##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1886881'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H19 N2 S +, C8 H7 O2 -'
_chemical_formula_sum     'C19 H26 N2 O2 S'
_chemical_formula_iupac     'C11 H19 N2 S +, C8 H7 O2 -'
_chemical_formula_weight     346.48
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P c'
_space_group_name_Hall     'P -2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    'x, -y, z+1/2'
_cell_length_a     10.1879(5)
_cell_length_b     11.6149(5)
_cell_length_c     8.7790(4)
_cell_angle_alpha     90
_cell_angle_beta     113.480(6)
_cell_angle_gamma     90
_cell_volume     952.82(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5914
_cell_measurement_theta_min     2.1700
_cell_measurement_theta_max     28.0830
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.240
_exptl_crystal_size_mid     0.110
_exptl_crystal_size_min     0.020
_exptl_crystal_density_diffrn     1.208
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     372
_exptl_absorpt_coefficient_mu     0.183
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2017)
;
_exptl_absorpt_correction_T_min     0.79337
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     173(2)
_diffrn_source     'rotating anode'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device_type     ' Rigaku XtaLAB P200 HPC '
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12189
_diffrn_reflns_av_R_equivalents     0.0290
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_theta_min     1.753
_diffrn_reflns_theta_max     29.024
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.882
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     4056
_reflns_number_gt     3440
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0497
_refine_ls_R_factor_gt     0.0377
_refine_ls_wR_factor_gt     0.0848
_refine_ls_wR_factor_ref     0.0892
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     4056
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0463P)²+0.0807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.203
_refine_diff_density_min     -0.172
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1371 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     0.03(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrystalClear-SM (Rigaku,  2017)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.3617(3) 0.6584(2) 0.8458(3) 0.0363(6) Uani d 1 . .
    C C2 0.2322(3) 0.6675(3) 0.8865(4) 0.0466(7) Uani d 1 . .
    C C3A 0.1685(10) 0.7939(8) 0.8152(12) 0.058(3) Uiso d 0.398(10) A 1
    H H3A1 0.0740 0.8028 0.8210 0.069 Uiso calc 0.398(10) A 1
    H H3A2 0.2329 0.8534 0.8878 0.069 Uiso calc 0.398(10) A 1
    C C4A 0.1525(10) 0.8143(9) 0.6457(13) 0.048(2) Uiso d 0.398(10) A 1
    H H4A1 0.1003 0.8874 0.6050 0.058 Uiso calc 0.398(10) A 1
    H H4A2 0.0957 0.7512 0.5735 0.058 Uiso calc 0.398(10) A 1
    C C3B 0.1217(6) 0.7333(5) 0.7440(7) 0.0467(18) Uiso d 0.602(10) A 2
    H H3B1 0.0401 0.7535 0.7730 0.056 Uiso calc 0.602(10) A 2
    H H3B2 0.0852 0.6836 0.6441 0.056 Uiso calc 0.602(10) A 2
    C C4B 0.1860(7) 0.8447(6) 0.7047(9) 0.0468(15) Uiso d 0.602(10) A 2
    H H4B1 0.1081 0.8907 0.6225 0.056 Uiso calc 0.602(10) A 2
    H H4B2 0.2291 0.8911 0.8074 0.056 Uiso calc 0.602(10) A 2
    C C5 0.3013(3) 0.8207(2) 0.6356(4) 0.0412(7) Uani d 1 . .
    C C6 0.3917(3) 0.7225(2) 0.7371(3) 0.0342(6) Uani d 1 . .
    C C7 0.5894(3) 0.6071(2) 0.8256(3) 0.0341(6) Uani d 1 . .
    C C8 0.1541(6) 0.5542(4) 0.8622(7) 0.111(2) Uani d 1 . .
    H H8A 0.0673 0.5643 0.8833 0.167 Uiso calc 1 . .
    H H8B 0.2164 0.4971 0.9397 0.167 Uiso calc 1 . .
    H H8C 0.1280 0.5275 0.7480 0.167 Uiso calc 1 . .
    C C9 0.2747(4) 0.7056(4) 1.0652(5) 0.0783(12) Uani d 1 . .
    H H9A 0.1884 0.7226 1.0847 0.117 Uiso calc 1 . .
    H H9B 0.3342 0.7749 1.0862 0.117 Uiso calc 1 . .
    H H9C 0.3288 0.6440 1.1401 0.117 Uiso calc 1 . .
    C C10 0.2527(4) 0.7945(3) 0.4504(4) 0.0648(10) Uani d 1 . .
    H H10A 0.1905 0.8566 0.3853 0.097 Uiso calc 1 . .
    H H10B 0.2000 0.7216 0.4246 0.097 Uiso calc 1 . .
    H H10C 0.3366 0.7886 0.4227 0.097 Uiso calc 1 . .
    C C11 0.3888(4) 0.9315(3) 0.6748(5) 0.0622(9) Uani d 1 . .
    H H11A 0.4216 0.9487 0.7935 0.093 Uiso calc 1 . .
    H H11B 0.3293 0.9950 0.6100 0.093 Uiso calc 1 . .
    H H11C 0.4718 0.9220 0.6461 0.093 Uiso calc 1 . .
    N N1 0.5199(2) 0.69242(19) 0.7257(3) 0.0352(5) Uani d 1 . .
    H H1N 0.559(3) 0.719(3) 0.660(4) 0.042 Uiso d 1 . .
    N N2 0.7129(3) 0.5644(2) 0.8356(3) 0.0406(6) Uani d 1 . .
    H H2N 0.738(3) 0.583(3) 0.759(4) 0.049 Uiso d 1 . .
    H H3N 0.742(3) 0.502(3) 0.900(4) 0.049 Uiso d 1 . .
    S S1 0.49793(8) 0.55753(6) 0.94144(8) 0.04197(19) Uani d 1 . .
    C C12 0.7414(3) 0.7561(2) 0.3383(3) 0.0353(6) Uani d 1 . .
    C C13 0.8440(3) 0.6995(3) 0.2992(3) 0.0393(6) Uani d 1 . .
    H H13 0.8915 0.6339 0.3613 0.047 Uiso calc 1 . .
    C C14 0.8774(3) 0.7387(3) 0.1694(3) 0.0428(7) Uani d 1 . .
    H H14 0.9470 0.6986 0.1432 0.051 Uiso calc 1 . .
    C C15 0.8121(3) 0.8343(3) 0.0779(4) 0.0457(7) Uani d 1 . .
    C C16 0.7089(4) 0.8898(3) 0.1168(4) 0.0533(8) Uani d 1 . .
    H H16 0.6618 0.9556 0.0547 0.064 Uiso calc 1 . .
    C C17 0.6734(3) 0.8509(3) 0.2443(4) 0.0474(8) Uani d 1 . .
    H H17 0.6015 0.8898 0.2678 0.057 Uiso calc 1 . .
    C C18 0.7053(3) 0.7165(2) 0.4803(3) 0.0382(6) Uani d 1 . .
    C C19 0.8510(4) 0.8777(4) -0.0609(4) 0.0688(10) Uani d 1 . .
    H H19A 0.8263 0.9595 -0.0806 0.103 Uiso calc 1 . .
    H H19B 0.7981 0.8339 -0.1624 0.103 Uiso calc 1 . .
    H H19C 0.9541 0.8680 -0.0298 0.103 Uiso calc 1 . .
    O O1 0.6233(2) 0.77900(19) 0.5192(3) 0.0518(5) Uani d 1 . .
    O O2 0.7604(2) 0.62322(16) 0.5523(2) 0.0428(5) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.338(4) ?
    C1 C2 . 1.502(4) ?
    C1 S1 . 1.753(3) ?
    C2 C8 . 1.509(5) ?
    C2 C3B . 1.514(6) ?
    C2 C9 . 1.518(5) ?
    C2 C3A . 1.626(9) ?
    C3A C4A . 1.451(14) ?
    C3A H3A1 . 0.9900 ?
    C3A H3A2 . 0.9900 ?
    C4A C5 . 1.555(9) ?
    C4A H4A1 . 0.9900 ?
    C4A H4A2 . 0.9900 ?
    C3B C4B . 1.551(9) ?
    C3B H3B1 . 0.9900 ?
    C3B H3B2 . 0.9900 ?
    C4B C5 . 1.547(6) ?
    C4B H4B1 . 0.9900 ?
    C4B H4B2 . 0.9900 ?
    C5 C6 . 1.514(4) ?
    C5 C11 . 1.524(4) ?
    C5 C10 . 1.529(4) ?
    C6 N1 . 1.394(4) ?
    C7 N2 . 1.322(4) ?
    C7 N1 . 1.325(3) ?
    C7 S1 . 1.729(3) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    N1 H1N . 0.88(3) ?
    N2 H2N . 0.83(3) ?
    N2 H3N . 0.89(3) ?
    C12 C17 . 1.385(4) ?
    C12 C13 . 1.389(4) ?
    C12 C18 . 1.506(4) ?
    C13 C14 . 1.389(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.377(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.386(4) ?
    C15 C19 . 1.510(4) ?
    C16 C17 . 1.383(4) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
    C18 O1 . 1.252(3) ?
    C18 O2 . 1.267(3) ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 127.0(3) ?
    C6 C1 S1 . . 110.6(2) ?
    C2 C1 S1 . . 122.4(2) ?
    C1 C2 C8 . . 111.6(3) ?
    C1 C2 C3B . . 105.9(3) ?
    C8 C2 C3B . . 98.4(4) ?
    C1 C2 C9 . . 110.6(3) ?
    C8 C2 C9 . . 108.5(3) ?
    C3B C2 C9 . . 121.2(4) ?
    C1 C2 C3A . . 103.1(4) ?
    C8 C2 C3A . . 128.8(5) ?
    C9 C2 C3A . . 92.3(4) ?
    C4A C3A C2 . . 114.0(8) ?
    C4A C3A H3A1 . . 108.8 ?
    C2 C3A H3A1 . . 108.8 ?
    C4A C3A H3A2 . . 108.8 ?
    C2 C3A H3A2 . . 108.8 ?
    H3A1 C3A H3A2 . . 107.7 ?
    C3A C4A C5 . . 110.6(8) ?
    C3A C4A H4A1 . . 109.5 ?
    C5 C4A H4A1 . . 109.5 ?
    C3A C4A H4A2 . . 109.5 ?
    C5 C4A H4A2 . . 109.5 ?
    H4A1 C4A H4A2 . . 108.1 ?
    C2 C3B C4B . . 111.3(5) ?
    C2 C3B H3B1 . . 109.4 ?
    C4B C3B H3B1 . . 109.4 ?
    C2 C3B H3B2 . . 109.4 ?
    C4B C3B H3B2 . . 109.4 ?
    H3B1 C3B H3B2 . . 108.0 ?
    C5 C4B C3B . . 113.0(5) ?
    C5 C4B H4B1 . . 109.0 ?
    C3B C4B H4B1 . . 109.0 ?
    C5 C4B H4B2 . . 109.0 ?
    C3B C4B H4B2 . . 109.0 ?
    H4B1 C4B H4B2 . . 107.8 ?
    C6 C5 C11 . . 109.8(2) ?
    C6 C5 C10 . . 109.8(2) ?
    C11 C5 C10 . . 108.7(3) ?
    C6 C5 C4B . . 106.5(3) ?
    C11 C5 C4B . . 103.1(4) ?
    C10 C5 C4B . . 118.6(4) ?
    C6 C5 C4A . . 107.9(4) ?
    C11 C5 C4A . . 121.6(5) ?
    C10 C5 C4A . . 98.1(5) ?
    C1 C6 N1 . . 113.5(2) ?
    C1 C6 C5 . . 125.6(3) ?
    N1 C6 C5 . . 121.0(2) ?
    N2 C7 N1 . . 124.6(2) ?
    N2 C7 S1 . . 123.9(2) ?
    N1 C7 S1 . . 111.6(2) ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C5 C11 H11A . . 109.5 ?
    C5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 N1 C6 . . 114.1(2) ?
    C7 N1 H1N . . 116(2) ?
    C6 N1 H1N . . 130.1(19) ?
    C7 N2 H2N . . 116(2) ?
    C7 N2 H3N . . 115(2) ?
    H2N N2 H3N . . 126(3) ?
    C7 S1 C1 . . 90.27(13) ?
    C17 C12 C13 . . 118.4(3) ?
    C17 C12 C18 . . 120.5(3) ?
    C13 C12 C18 . . 121.1(3) ?
    C14 C13 C12 . . 120.2(3) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 121.6(3) ?
    C15 C14 H14 . . 119.2 ?
    C13 C14 H14 . . 119.2 ?
    C14 C15 C16 . . 117.9(3) ?
    C14 C15 C19 . . 121.2(3) ?
    C16 C15 C19 . . 120.8(3) ?
    C17 C16 C15 . . 121.1(3) ?
    C17 C16 H16 . . 119.4 ?
    C15 C16 H16 . . 119.4 ?
    C16 C17 C12 . . 120.8(3) ?
    C16 C17 H17 . . 119.6 ?
    C12 C17 H17 . . 119.6 ?
    O1 C18 O2 . . 124.9(2) ?
    O1 C18 C12 . . 117.2(3) ?
    O2 C18 C12 . . 117.9(2) ?
    C15 C19 H19A . . 109.5 ?
    C15 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C15 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1N O1 . 0.88(3) 1.76(3) 2.632(3) 175(3)
    N2 H2N O2 . 0.83(3) 1.98(4) 2.801(3) 170(3)
    N2 H3N O2 2_565 0.89(3) 1.93(3) 2.805(3) 164(3)
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.957
_shelx_estimated_absorpt_T_max     0.996
data_II
_database_code_depnum_ccdc_archive 'CCDC 1886882'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H19 N2 S +, C7 H4 Br O2 -'
_chemical_formula_sum     'C18 H23 Br N2 O2 S'
_chemical_formula_iupac     'C11 H19 N2 S +, C7 H4 Br O2 -'
_chemical_formula_weight     411.35
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P c'
_space_group_name_Hall     'P -2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    'x, -y, z+1/2'
_cell_length_a     10.2506(5)
_cell_length_b     11.5855(4)
_cell_length_c     8.8269(4)
_cell_angle_alpha     90
_cell_angle_beta     113.807(6)
_cell_angle_gamma     90
_cell_volume     959.07(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6835
_cell_measurement_theta_min     2.1870
_cell_measurement_theta_max     28.2070
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.120
_exptl_crystal_size_mid     0.080
_exptl_crystal_size_min     0.020
_exptl_crystal_density_diffrn     1.424
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     2.264
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2017)
;
_exptl_absorpt_correction_T_min     0.76058
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     173(2)
_diffrn_source     'rotating anode'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device_type     ' Rigaku XtaLAB P200 HPC '
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12220
_diffrn_reflns_av_R_equivalents     0.0261
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_theta_min     2.172
_diffrn_reflns_theta_max     29.061
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.859
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     11
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     3993
_reflns_number_gt     3311
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0432
_refine_ls_R_factor_gt     0.0323
_refine_ls_wR_factor_gt     0.0793
_refine_ls_wR_factor_ref     0.0826
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     3993
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0407P)²+0.0111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.621
_refine_diff_density_min     -0.380
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1344 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     0.005(4)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrystalClear-SM (Rigaku,  2017)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.6357(4) 0.6587(3) 0.1418(5) 0.0359(8) Uani d 1 . .
    C C2 0.7655(5) 0.6679(4) 0.1027(5) 0.0446(9) Uani d 1 . .
    C C3 0.8711(8) 0.7399(8) 0.2385(10) 0.113(3) Uani d 1 . .
    H H3A 0.9213 0.6883 0.3338 0.136 Uiso calc 1 . .
    H H3B 0.9431 0.7681 0.1991 0.136 Uiso calc 1 . .
    C C4 0.8218(6) 0.8359(5) 0.2982(9) 0.0780(17) Uani d 1 . .
    H H4A 0.7931 0.8956 0.2105 0.094 Uiso calc 1 . .
    H H4B 0.9040 0.8673 0.3937 0.094 Uiso calc 1 . .
    C C5 0.6976(4) 0.8213(3) 0.3532(5) 0.0403(9) Uani d 1 . .
    C C6 0.6067(4) 0.7238(3) 0.2502(5) 0.0339(8) Uani d 1 . .
    C C7 0.4084(4) 0.6086(3) 0.1598(5) 0.0345(8) Uani d 1 . .
    C C8 0.8389(8) 0.5492(7) 0.1190(12) 0.110(3) Uani d 1 . .
    H H8A 0.9299 0.5590 0.1087 0.164 Uiso calc 1 . .
    H H8B 0.7771 0.4976 0.0314 0.164 Uiso calc 1 . .
    H H8C 0.8561 0.5156 0.2274 0.164 Uiso calc 1 . .
    C C9 0.7278(7) 0.7092(6) -0.0719(7) 0.0772(17) Uani d 1 . .
    H H9A 0.8147 0.7152 -0.0923 0.116 Uiso calc 1 . .
    H H9B 0.6820 0.7850 -0.0868 0.116 Uiso calc 1 . .
    H H9C 0.6622 0.6541 -0.1501 0.116 Uiso calc 1 . .
    C C10 0.7484(6) 0.7930(5) 0.5371(6) 0.0664(14) Uani d 1 . .
    H H10A 0.8122 0.8542 0.6028 0.100 Uiso calc 1 . .
    H H10B 0.7995 0.7193 0.5604 0.100 Uiso calc 1 . .
    H H10C 0.6659 0.7875 0.5663 0.100 Uiso calc 1 . .
    C C11 0.6095(6) 0.9320(4) 0.3150(6) 0.0578(12) Uani d 1 . .
    H H11A 0.5714 0.9473 0.1957 0.087 Uiso calc 1 . .
    H H11B 0.6699 0.9966 0.3751 0.087 Uiso calc 1 . .
    H H11C 0.5304 0.9231 0.3496 0.087 Uiso calc 1 . .
    N N1 0.4781(3) 0.6939(3) 0.2604(4) 0.0348(7) Uani d 1 . .
    H H1N 0.441(5) 0.732(4) 0.339(5) 0.042 Uiso d 1 . .
    N N2 0.2855(4) 0.5667(3) 0.1482(5) 0.0408(8) Uani d 1 . .
    H H2N 0.257(6) 0.582(4) 0.208(6) 0.049 Uiso d 1 . .
    H H3N 0.264(5) 0.505(4) 0.086(6) 0.049 Uiso d 1 . .
    S S1 0.49893(11) 0.55873(9) 0.04481(11) 0.0398(2) Uani d 1 . .
    C C12 0.2601(4) 0.7536(3) 0.6483(4) 0.0352(8) Uani d 1 . .
    C C13 0.1566(4) 0.6980(3) 0.6846(5) 0.0369(8) Uani d 1 . .
    H H13 0.1094 0.6326 0.6213 0.044 Uiso calc 1 . .
    C C14 0.1208(4) 0.7360(4) 0.8116(5) 0.0422(9) Uani d 1 . .
    H H14 0.0501 0.6970 0.8361 0.051 Uiso calc 1 . .
    C C15 0.1893(4) 0.8310(4) 0.9017(5) 0.0402(9) Uani d 1 . .
    C C16 0.2946(5) 0.8860(3) 0.8709(6) 0.0490(11) Uani d 1 . .
    H H16 0.3434 0.9499 0.9369 0.059 Uiso calc 1 . .
    C C17 0.3291(5) 0.8481(4) 0.7443(5) 0.0466(10) Uani d 1 . .
    H H17 0.4009 0.8871 0.7220 0.056 Uiso calc 1 . .
    C C18 0.2979(4) 0.7141(3) 0.5095(5) 0.0370(8) Uani d 1 . .
    O O1 0.3836(4) 0.7755(3) 0.4748(4) 0.0505(7) Uani d 1 . .
    O O2 0.2410(3) 0.6225(2) 0.4343(4) 0.0419(6) Uani d 1 . .
    Br Br1 0.13945(5) 0.88476(4) 1.07398(5) 0.0676(2) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.342(5) ?
    C1 C2 . 1.508(6) ?
    C1 S1 . 1.752(4) ?
    C2 C3 . 1.503(8) ?
    C2 C9 . 1.507(7) ?
    C2 C8 . 1.546(8) ?
    C3 C4 . 1.408(10) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.544(7) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.513(6) ?
    C5 C11 . 1.526(6) ?
    C5 C10 . 1.528(6) ?
    C6 N1 . 1.400(5) ?
    C7 N2 . 1.316(5) ?
    C7 N1 . 1.327(5) ?
    C7 S1 . 1.728(4) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    N1 H1N . 1.01(5) ?
    N2 H2N . 0.72(5) ?
    N2 H3N . 0.88(5) ?
    C12 C13 . 1.385(5) ?
    C12 C17 . 1.391(6) ?
    C12 C18 . 1.498(5) ?
    C13 C14 . 1.385(5) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.374(6) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.371(6) ?
    C15 Br1 . 1.895(4) ?
    C16 C17 . 1.373(7) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
    C18 O1 . 1.260(5) ?
    C18 O2 . 1.263(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 126.4(4) ?
    C6 C1 S1 . . 110.8(3) ?
    C2 C1 S1 . . 122.7(3) ?
    C3 C2 C9 . . 116.4(5) ?
    C3 C2 C1 . . 105.9(4) ?
    C9 C2 C1 . . 111.8(4) ?
    C3 C2 C8 . . 104.7(6) ?
    C9 C2 C8 . . 107.0(5) ?
    C1 C2 C8 . . 110.9(4) ?
    C4 C3 C2 . . 119.0(6) ?
    C4 C3 H3A . . 107.6 ?
    C2 C3 H3A . . 107.6 ?
    C4 C3 H3B . . 107.6 ?
    C2 C3 H3B . . 107.6 ?
    H3A C3 H3B . . 107.0 ?
    C3 C4 C5 . . 119.8(5) ?
    C3 C4 H4A . . 107.4 ?
    C5 C4 H4A . . 107.4 ?
    C3 C4 H4B . . 107.4 ?
    C5 C4 H4B . . 107.4 ?
    H4A C4 H4B . . 106.9 ?
    C6 C5 C11 . . 109.2(3) ?
    C6 C5 C10 . . 110.0(3) ?
    C11 C5 C10 . . 109.4(4) ?
    C6 C5 C4 . . 106.2(4) ?
    C11 C5 C4 . . 109.2(4) ?
    C10 C5 C4 . . 112.8(5) ?
    C1 C6 N1 . . 113.1(3) ?
    C1 C6 C5 . . 126.0(3) ?
    N1 C6 C5 . . 120.9(3) ?
    N2 C7 N1 . . 124.5(4) ?
    N2 C7 S1 . . 123.7(3) ?
    N1 C7 S1 . . 111.7(3) ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C5 C11 H11A . . 109.5 ?
    C5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 N1 C6 . . 114.0(3) ?
    C7 N1 H1N . . 122(2) ?
    C6 N1 H1N . . 124(2) ?
    C7 N2 H2N . . 121(4) ?
    C7 N2 H3N . . 110(3) ?
    H2N N2 H3N . . 126(5) ?
    C7 S1 C1 . . 90.29(18) ?
    C13 C12 C17 . . 118.3(4) ?
    C13 C12 C18 . . 121.5(3) ?
    C17 C12 C18 . . 120.2(4) ?
    C14 C13 C12 . . 121.2(4) ?
    C14 C13 H13 . . 119.4 ?
    C12 C13 H13 . . 119.4 ?
    C15 C14 C13 . . 118.9(4) ?
    C15 C14 H14 . . 120.6 ?
    C13 C14 H14 . . 120.6 ?
    C16 C15 C14 . . 121.2(4) ?
    C16 C15 Br1 . . 119.7(3) ?
    C14 C15 Br1 . . 119.2(3) ?
    C15 C16 C17 . . 119.6(4) ?
    C15 C16 H16 . . 120.2 ?
    C17 C16 H16 . . 120.2 ?
    C16 C17 C12 . . 120.9(4) ?
    C16 C17 H17 . . 119.5 ?
    C12 C17 H17 . . 119.5 ?
    O1 C18 O2 . . 124.5(4) ?
    O1 C18 C12 . . 117.5(4) ?
    O2 C18 C12 . . 118.0(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1N O1 . 1.01(5) 1.62(5) 2.626(4) 172(4)
    N2 H2N O2 . 0.72(5) 2.12(5) 2.816(5) 162(6)
    N2 H3N O2 2_564 0.88(5) 1.94(5) 2.808(5) 170(4)
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.773
_shelx_estimated_absorpt_T_max     0.956
data_III
_database_code_depnum_ccdc_archive 'CCDC 1886883'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H19 N2 S +, C7 H3 N2 O6 -'
_chemical_formula_sum     'C18 H22 N4 O6 S'
_chemical_formula_iupac     'C11 H19 N2 S +, C7 H3 N2 O6 -'
_chemical_formula_weight     422.45
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     17.3232(6)
_cell_length_b     5.84087(17)
_cell_length_c     21.0876(8)
_cell_angle_alpha     90
_cell_angle_beta     109.875(4)
_cell_angle_gamma     90
_cell_volume     2006.60(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10667
_cell_measurement_theta_min     2.0370
_cell_measurement_theta_max     27.7580
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.270
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.030
_exptl_crystal_density_diffrn     1.398
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     888
_exptl_absorpt_coefficient_mu     0.205
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2017)
;
_exptl_absorpt_correction_T_min     0.56607
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     173(2)
_diffrn_source     'rotating anode'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device_type     ' Rigaku XtaLAB P200 HPC '
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     25034
_diffrn_reflns_av_R_equivalents     0.0559
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_theta_min     1.868
_diffrn_reflns_theta_max     29.165
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.870
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     4698
_reflns_number_gt     3712
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0565
_refine_ls_R_factor_gt     0.0420
_refine_ls_wR_factor_gt     0.1079
_refine_ls_wR_factor_ref     0.1155
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     4698
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0567P)²+0.5151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.494
_refine_diff_density_min     -0.252
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrystalClear-SM (Rigaku,  2017)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.26545(9) 0.4584(3) 0.49126(7) 0.0264(3) Uani d 1 . .
    C C2 0.19150(9) 0.3629(3) 0.50428(8) 0.0298(3) Uani d 1 . .
    C C3 0.13800(10) 0.2456(3) 0.43879(9) 0.0419(4) Uani d 1 . .
    H H3A 0.0996 0.1392 0.4494 0.050 Uiso calc 1 . .
    H H3B 0.1048 0.3636 0.4077 0.050 Uiso calc 1 . .
    C C4 0.18675(11) 0.1131(3) 0.40303(9) 0.0397(4) Uani d 1 . .
    H H4A 0.1479 0.0344 0.3634 0.048 Uiso calc 1 . .
    H H4B 0.2196 -0.0059 0.4340 0.048 Uiso calc 1 . .
    C C5 0.24503(10) 0.2636(3) 0.37920(8) 0.0319(4) Uani d 1 . .
    C C6 0.28907(9) 0.4173(3) 0.43809(7) 0.0260(3) Uani d 1 . .
    C C7 0.39559(9) 0.6469(3) 0.49858(7) 0.0266(3) Uani d 1 . .
    C C8 0.21999(11) 0.1932(3) 0.56307(9) 0.0388(4) Uani d 1 . .
    H H8A 0.1720 0.1286 0.5713 0.058 Uiso calc 1 . .
    H H8B 0.2547 0.2727 0.6037 0.058 Uiso calc 1 . .
    H H8C 0.2514 0.0697 0.5518 0.058 Uiso calc 1 . .
    C C9 0.14165(11) 0.5539(3) 0.52232(10) 0.0427(4) Uani d 1 . .
    H H9A 0.0925 0.4881 0.5283 0.064 Uiso calc 1 . .
    H H9B 0.1253 0.6672 0.4859 0.064 Uiso calc 1 . .
    H H9C 0.1753 0.6282 0.5643 0.064 Uiso calc 1 . .
    C C10 0.30657(12) 0.1076(3) 0.36271(10) 0.0442(4) Uani d 1 . .
    H H10A 0.2769 -0.0070 0.3294 0.066 Uiso calc 1 . .
    H H10B 0.3410 0.0304 0.4039 0.066 Uiso calc 1 . .
    H H10C 0.3413 0.1996 0.3443 0.066 Uiso calc 1 . .
    C C11 0.19849(13) 0.4072(4) 0.31745(9) 0.0516(5) Uani d 1 . .
    H H11A 0.1707 0.3058 0.2795 0.077 Uiso calc 1 . .
    H H11B 0.2372 0.5057 0.3054 0.077 Uiso calc 1 . .
    H H11C 0.1577 0.5024 0.3278 0.077 Uiso calc 1 . .
    N N1 0.36224(8) 0.5279(2) 0.44229(6) 0.0271(3) Uani d 1 . .
    H H1N 0.3856(11) 0.524(3) 0.4110(9) 0.033 Uiso d 1 . .
    N N2 0.46553(9) 0.7605(3) 0.51363(7) 0.0337(3) Uani d 1 . .
    H H2N 0.4887(12) 0.780(3) 0.4812(10) 0.040 Uiso d 1 . .
    H H3N 0.4791(12) 0.857(3) 0.5486(10) 0.040 Uiso d 1 . .
    S S1 0.33701(2) 0.63371(7) 0.55004(2) 0.02882(12) Uani d 1 . .
    C C12 0.53091(9) 0.7205(3) 0.30278(7) 0.0283(3) Uani d 1 . .
    C C13 0.58549(9) 0.8968(3) 0.30559(8) 0.0304(3) Uani d 1 . .
    H H13 0.5992 1.0042 0.3416 0.037 Uiso calc 1 . .
    C C14 0.61975(9) 0.9144(3) 0.25552(8) 0.0313(4) Uani d 1 . .
    C C15 0.60233(9) 0.7633(3) 0.20218(8) 0.0327(4) Uani d 1 . .
    H H15 0.6256 0.7796 0.1676 0.039 Uiso calc 1 . .
    C C16 0.54918(9) 0.5872(3) 0.20198(8) 0.0306(3) Uani d 1 . .
    C C17 0.51322(9) 0.5616(3) 0.25084(7) 0.0294(3) Uani d 1 . .
    H H17 0.4770 0.4375 0.2489 0.035 Uiso calc 1 . .
    C C18 0.49110(10) 0.7013(3) 0.35667(8) 0.0312(3) Uani d 1 . .
    N N3 0.67709(8) 1.1050(3) 0.25924(7) 0.0380(3) Uani d 1 . .
    N N4 0.52907(8) 0.4200(3) 0.14618(7) 0.0386(4) Uani d 1 . .
    O O1 0.43858(8) 0.5479(2) 0.34910(6) 0.0427(3) Uani d 1 . .
    O O2 0.51480(8) 0.8407(2) 0.40440(6) 0.0410(3) Uani d 1 . .
    O O3 0.69300(8) 1.1515(2) 0.20855(7) 0.0500(4) Uani d 1 . .
    O O4 0.70535(9) 1.2066(3) 0.31259(7) 0.0596(4) Uani d 1 . .
    O O5 0.49224(9) 0.2464(3) 0.15173(7) 0.0508(3) Uani d 1 . .
    O O6 0.54967(8) 0.4645(3) 0.09754(6) 0.0522(4) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.340(2) ?
    C1 C2 . 1.506(2) ?
    C1 S1 . 1.7540(15) ?
    C2 C8 . 1.532(2) ?
    C2 C9 . 1.535(2) ?
    C2 C3 . 1.538(2) ?
    C3 C4 . 1.521(3) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.546(2) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.512(2) ?
    C5 C11 . 1.528(2) ?
    C5 C10 . 1.529(2) ?
    C6 N1 . 1.3981(19) ?
    C7 N2 . 1.322(2) ?
    C7 N1 . 1.3267(19) ?
    C7 S1 . 1.7211(15) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    N1 H1N . 0.885(19) ?
    N2 H2N . 0.91(2) ?
    N2 H3N . 0.90(2) ?
    C12 C13 . 1.385(2) ?
    C12 C17 . 1.388(2) ?
    C12 C18 . 1.521(2) ?
    C13 C14 . 1.380(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.380(2) ?
    C14 N3 . 1.476(2) ?
    C15 C16 . 1.380(2) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.381(2) ?
    C16 N4 . 1.477(2) ?
    C17 H17 . 0.9500 ?
    C18 O1 . 1.2475(19) ?
    C18 O2 . 1.2506(19) ?
    N3 O4 . 1.2178(19) ?
    N3 O3 . 1.2218(18) ?
    N4 O6 . 1.2231(19) ?
    N4 O5 . 1.224(2) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 127.39(14) ?
    C6 C1 S1 . . 110.64(11) ?
    C2 C1 S1 . . 121.88(11) ?
    C1 C2 C8 . . 109.11(13) ?
    C1 C2 C9 . . 111.17(13) ?
    C8 C2 C9 . . 108.85(13) ?
    C1 C2 C3 . . 106.95(12) ?
    C8 C2 C3 . . 111.61(14) ?
    C9 C2 C3 . . 109.15(14) ?
    C4 C3 C2 . . 113.90(14) ?
    C4 C3 H3A . . 108.8 ?
    C2 C3 H3A . . 108.8 ?
    C4 C3 H3B . . 108.8 ?
    C2 C3 H3B . . 108.8 ?
    H3A C3 H3B . . 107.7 ?
    C3 C4 C5 . . 113.96(15) ?
    C3 C4 H4A . . 108.8 ?
    C5 C4 H4A . . 108.8 ?
    C3 C4 H4B . . 108.8 ?
    C5 C4 H4B . . 108.8 ?
    H4A C4 H4B . . 107.7 ?
    C6 C5 C11 . . 110.26(14) ?
    C6 C5 C10 . . 110.14(13) ?
    C11 C5 C10 . . 109.86(15) ?
    C6 C5 C4 . . 105.88(12) ?
    C11 C5 C4 . . 112.06(15) ?
    C10 C5 C4 . . 108.56(14) ?
    C1 C6 N1 . . 113.12(13) ?
    C1 C6 C5 . . 125.55(13) ?
    N1 C6 C5 . . 121.31(12) ?
    N2 C7 N1 . . 124.23(14) ?
    N2 C7 S1 . . 124.04(12) ?
    N1 C7 S1 . . 111.72(11) ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C5 C11 H11A . . 109.5 ?
    C5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 N1 C6 . . 114.09(12) ?
    C7 N1 H1N . . 120.8(12) ?
    C6 N1 H1N . . 125.1(12) ?
    C7 N2 H2N . . 119.0(12) ?
    C7 N2 H3N . . 118.5(12) ?
    H2N N2 H3N . . 118.8(17) ?
    C7 S1 C1 . . 90.40(7) ?
    C13 C12 C17 . . 119.67(14) ?
    C13 C12 C18 . . 119.95(14) ?
    C17 C12 C18 . . 120.38(14) ?
    C14 C13 C12 . . 119.18(15) ?
    C14 C13 H13 . . 120.4 ?
    C12 C13 H13 . . 120.4 ?
    C13 C14 C15 . . 122.97(15) ?
    C13 C14 N3 . . 118.18(15) ?
    C15 C14 N3 . . 118.85(14) ?
    C16 C15 C14 . . 116.12(14) ?
    C16 C15 H15 . . 121.9 ?
    C14 C15 H15 . . 121.9 ?
    C15 C16 C17 . . 123.23(15) ?
    C15 C16 N4 . . 118.16(14) ?
    C17 C16 N4 . . 118.60(15) ?
    C16 C17 C12 . . 118.79(15) ?
    C16 C17 H17 . . 120.6 ?
    C12 C17 H17 . . 120.6 ?
    O1 C18 O2 . . 126.60(14) ?
    O1 C18 C12 . . 116.98(14) ?
    O2 C18 C12 . . 116.42(13) ?
    O4 N3 O3 . . 124.09(15) ?
    O4 N3 C14 . . 117.95(13) ?
    O3 N3 C14 . . 117.96(15) ?
    O6 N4 O5 . . 124.50(15) ?
    O6 N4 C16 . . 118.07(16) ?
    O5 N4 C16 . . 117.43(14) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C8 . . . . 109.98(18) ?
    S1 C1 C2 C8 . . . . -66.27(17) ?
    C6 C1 C2 C9 . . . . -129.96(17) ?
    S1 C1 C2 C9 . . . . 53.79(18) ?
    C6 C1 C2 C3 . . . . -10.9(2) ?
    S1 C1 C2 C3 . . . . 172.86(12) ?
    C1 C2 C3 C4 . . . . 40.0(2) ?
    C8 C2 C3 C4 . . . . -79.31(18) ?
    C9 C2 C3 C4 . . . . 160.33(15) ?
    C2 C3 C4 C5 . . . . -62.4(2) ?
    C3 C4 C5 C6 . . . . 46.04(19) ?
    C3 C4 C5 C11 . . . . -74.21(19) ?
    C3 C4 C5 C10 . . . . 164.27(15) ?
    C2 C1 C6 N1 . . . . -178.20(14) ?
    S1 C1 C6 N1 . . . . -1.60(17) ?
    C2 C1 C6 C5 . . . . 0.1(3) ?
    S1 C1 C6 C5 . . . . 176.71(13) ?
    C11 C5 C6 C1 . . . . 104.46(19) ?
    C10 C5 C6 C1 . . . . -134.13(17) ?
    C4 C5 C6 C1 . . . . -16.9(2) ?
    C11 C5 C6 N1 . . . . -77.36(19) ?
    C10 C5 C6 N1 . . . . 44.0(2) ?
    C4 C5 C6 N1 . . . . 161.23(14) ?
    N2 C7 N1 C6 . . . . 178.54(15) ?
    S1 C7 N1 C6 . . . . -1.05(17) ?
    C1 C6 N1 C7 . . . . 1.76(19) ?
    C5 C6 N1 C7 . . . . -176.63(14) ?
    N2 C7 S1 C1 . . . . -179.48(15) ?
    N1 C7 S1 C1 . . . . 0.11(12) ?
    C6 C1 S1 C7 . . . . 0.86(12) ?
    C2 C1 S1 C7 . . . . 177.68(13) ?
    C17 C12 C13 C14 . . . . 1.7(2) ?
    C18 C12 C13 C14 . . . . -178.67(14) ?
    C12 C13 C14 C15 . . . . -0.1(2) ?
    C12 C13 C14 N3 . . . . 179.39(13) ?
    C13 C14 C15 C16 . . . . -1.3(2) ?
    N3 C14 C15 C16 . . . . 179.18(13) ?
    C14 C15 C16 C17 . . . . 1.3(2) ?
    C14 C15 C16 N4 . . . . -179.58(13) ?
    C15 C16 C17 C12 . . . . 0.2(2) ?
    N4 C16 C17 C12 . . . . -178.97(14) ?
    C13 C12 C17 C16 . . . . -1.7(2) ?
    C18 C12 C17 C16 . . . . 178.65(14) ?
    C13 C12 C18 O1 . . . . 175.54(15) ?
    C17 C12 C18 O1 . . . . -4.8(2) ?
    C13 C12 C18 O2 . . . . -4.8(2) ?
    C17 C12 C18 O2 . . . . 174.86(15) ?
    C13 C14 N3 O4 . . . . 15.8(2) ?
    C15 C14 N3 O4 . . . . -164.70(16) ?
    C13 C14 N3 O3 . . . . -164.01(15) ?
    C15 C14 N3 O3 . . . . 15.5(2) ?
    C15 C16 N4 O6 . . . . -11.4(2) ?
    C17 C16 N4 O6 . . . . 167.84(14) ?
    C15 C16 N4 O5 . . . . 169.17(14) ?
    C17 C16 N4 O5 . . . . -11.6(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1N O1 . 0.885(19) 1.838(19) 2.7187(17) 173.4(17)
    N2 H3N O2 3_676 0.90(2) 2.01(2) 2.8509(19) 156.3(17)
    N2 H2N O2 . 0.91(2) 1.86(2) 2.7551(18) 168.3(18)
    C8 H8A O6 4_566 0.98 2.43 3.397(2) 170
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.947
_shelx_estimated_absorpt_T_max     0.994
data_IV
_database_code_depnum_ccdc_archive 'CCDC 1886884'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C11 H19 N2 S +), C4 H2 O4 2-'
_chemical_formula_sum     'C26 H40 N4 O4 S2'
_chemical_formula_iupac     '2C11 H19 N2 S +, C4 H2 O4 2-'
_chemical_formula_weight     536.74
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.0259(6)
_cell_length_b     14.7314(11)
_cell_length_c     11.1993(8)
_cell_angle_alpha     90
_cell_angle_beta     101.943(6)
_cell_angle_gamma     90
_cell_volume     1456.87(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4569
_cell_measurement_theta_min     2.3020
_cell_measurement_theta_max     23.7150
_cell_measurement_temperature     173(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.150
_exptl_crystal_size_mid     0.080
_exptl_crystal_size_min     0.020
_exptl_crystal_density_diffrn     1.224
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.219
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2017)
;
_exptl_absorpt_correction_T_min     0.33291
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     173(2)
_diffrn_source     'rotating anode'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device_type     ' Rigaku XtaLAB P200 HPC '
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19263
_diffrn_reflns_av_R_equivalents     0.0803
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_theta_min     1.859
_diffrn_reflns_theta_max     29.099
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.866
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     12
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     6424
_reflns_number_gt     3792
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1297
_refine_ls_R_factor_gt     0.0624
_refine_ls_wR_factor_gt     0.1099
_refine_ls_wR_factor_ref     0.1275
_refine_ls_goodness_of_fit_ref     1.002
_refine_ls_restrained_S_all     1.002
_refine_ls_number_reflns     6424
_refine_ls_number_parameters     350
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.266
_refine_diff_density_min     -0.257
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1279 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     0.46(7)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrystalClear-SM (Rigaku,  2017)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 1.2869(6) 0.3952(4) 0.6937(4) 0.0339(13) Uani d 1 . .
    C C2 1.3939(6) 0.4406(4) 0.7989(5) 0.0467(15) Uani d 1 . .
    C C3A 1.2984(8) 0.5068(7) 0.8546(8) 0.052(3) Uiso d 0.78(2) A 1
    H H3A1 1.2720 0.5596 0.7996 0.062 Uiso calc 0.78(2) A 1
    H H3A2 1.3578 0.5293 0.9334 0.062 Uiso calc 0.78(2) A 1
    C C4A 1.1520(10) 0.4615(8) 0.8755(8) 0.047(2) Uiso d 0.78(2) A 1
    H H4A1 1.1017 0.5022 0.9252 0.056 Uiso calc 0.78(2) A 1
    H H4A2 1.1780 0.4044 0.9216 0.056 Uiso calc 0.78(2) A 1
    C C3B 1.284(3) 0.456(3) 0.899(3) 0.063(12) Uiso d 0.22(2) A 2
    H H3B1 1.2677 0.3968 0.9362 0.075 Uiso calc 0.22(2) A 2
    H H3B2 1.3377 0.4959 0.9657 0.075 Uiso calc 0.22(2) A 2
    C C4B 1.130(3) 0.498(2) 0.846(3) 0.033(8) Uiso d 0.22(2) A 2
    H H4B1 1.0735 0.5078 0.9121 0.039 Uiso calc 0.22(2) A 2
    H H4B2 1.1445 0.5582 0.8102 0.039 Uiso calc 0.22(2) A 2
    C C5 1.0394(6) 0.4401(4) 0.7513(4) 0.0372(13) Uani d 1 . .
    C C6 1.1349(6) 0.3955(3) 0.6728(4) 0.0312(13) Uani d 1 . .
    C C7 1.1687(6) 0.3114(3) 0.5087(4) 0.0320(13) Uani d 1 . .
    C C8 1.4824(7) 0.3683(4) 0.8815(6) 0.067(2) Uani d 1 . .
    H H8A 1.5474 0.3975 0.9519 0.101 Uiso calc 1 . .
    H H8B 1.5451 0.3337 0.8359 0.101 Uiso calc 1 . .
    H H8C 1.4115 0.3272 0.9098 0.101 Uiso calc 1 . .
    C C9 1.5096(8) 0.4998(5) 0.7490(6) 0.076(2) Uani d 1 . .
    H H9A 1.5751 0.5316 0.8168 0.114 Uiso calc 1 . .
    H H9B 1.4553 0.5443 0.6909 0.114 Uiso calc 1 . .
    H H9C 1.5715 0.4610 0.7077 0.114 Uiso calc 1 . .
    C C10 0.9232(6) 0.3732(4) 0.7813(5) 0.0506(16) Uani d 1 . .
    H H10A 0.8700 0.4009 0.8400 0.076 Uiso calc 1 . .
    H H10B 0.9750 0.3180 0.8167 0.076 Uiso calc 1 . .
    H H10C 0.8501 0.3578 0.7065 0.076 Uiso calc 1 . .
    C C11 0.9553(8) 0.5223(5) 0.6843(6) 0.070(2) Uani d 1 . .
    H H11A 0.8941 0.5512 0.7364 0.105 Uiso calc 1 . .
    H H11B 0.8892 0.5020 0.6083 0.105 Uiso calc 1 . .
    H H11C 1.0291 0.5661 0.6656 0.105 Uiso calc 1 . .
    N N1 1.0694(5) 0.3476(3) 0.5669(4) 0.0298(11) Uani d 1 . .
    H H1N 0.976(6) 0.334(4) 0.544(4) 0.036 Uiso d 1 . .
    N N2 1.1307(6) 0.2614(4) 0.4096(4) 0.0452(13) Uani d 1 . .
    H H2N 1.029(7) 0.263(4) 0.369(5) 0.054 Uiso d 1 . .
    H H3N 1.202(6) 0.248(4) 0.365(5) 0.054 Uiso d 1 . .
    S S1 1.35226(14) 0.33370(9) 0.58194(12) 0.0396(4) Uani d 1 . .
    C C12 -0.1633(6) 0.1107(4) -0.1894(4) 0.0340(13) Uani d 1 . .
    C C13 -0.2578(6) 0.0698(4) -0.3022(5) 0.0408(14) Uani d 1 . .
    C C14 -0.1503(6) 0.0460(4) -0.3869(5) 0.0501(16) Uani d 1 . .
    H H14A -0.2031 0.0048 -0.4519 0.060 Uiso calc 1 . .
    H H14B -0.1244 0.1022 -0.4265 0.060 Uiso calc 1 . .
    C C15 -0.0046(6) 0.0005(4) -0.3204(5) 0.0493(15) Uani d 1 . .
    H H15A 0.0557 -0.0170 -0.3813 0.059 Uiso calc 1 . .
    H H15B -0.0312 -0.0558 -0.2816 0.059 Uiso calc 1 . .
    C C16 0.0948(6) 0.0599(4) -0.2219(4) 0.0353(13) Uani d 1 . .
    C C17 -0.0114(5) 0.1088(3) -0.1552(4) 0.0286(12) Uani d 1 . .
    C C18 -0.0619(6) 0.1945(4) 0.0014(5) 0.0338(13) Uani d 1 . .
    C C19 -0.3410(7) -0.0144(4) -0.2709(6) 0.0662(19) Uani d 1 . .
    H H19A -0.4097 -0.0366 -0.3446 0.099 Uiso calc 1 . .
    H H19B -0.3995 0.0012 -0.2092 0.099 Uiso calc 1 . .
    H H19C -0.2672 -0.0618 -0.2389 0.099 Uiso calc 1 . .
    C C20 -0.3760(6) 0.1378(4) -0.3673(6) 0.0556(17) Uani d 1 . .
    H H20A -0.4356 0.1098 -0.4412 0.083 Uiso calc 1 . .
    H H20B -0.3246 0.1919 -0.3896 0.083 Uiso calc 1 . .
    H H20C -0.4432 0.1552 -0.3127 0.083 Uiso calc 1 . .
    C C21 0.2029(6) -0.0017(4) -0.1334(5) 0.0498(15) Uani d 1 . .
    H H21A 0.2615 -0.0391 -0.1793 0.075 Uiso calc 1 . .
    H H21B 0.1441 -0.0412 -0.0901 0.075 Uiso calc 1 . .
    H H21C 0.2720 0.0357 -0.0743 0.075 Uiso calc 1 . .
    C C22 0.1855(7) 0.1290(4) -0.2784(5) 0.0520(17) Uani d 1 . .
    H H22A 0.2544 0.0971 -0.3212 0.078 Uiso calc 1 . .
    H H22B 0.2443 0.1671 -0.2140 0.078 Uiso calc 1 . .
    H H22C 0.1162 0.1671 -0.3364 0.078 Uiso calc 1 . .
    N N3 0.0446(5) 0.1575(3) -0.0477(4) 0.0329(11) Uani d 1 . .
    H H4N 0.151(6) 0.163(4) -0.013(4) 0.040 Uiso d 1 . .
    N N4 -0.0317(6) 0.2444(4) 0.1013(4) 0.0457(13) Uani d 1 . .
    H H5N 0.078(7) 0.242(4) 0.141(5) 0.055 Uiso d 1 . .
    H H6N -0.104(7) 0.256(4) 0.130(5) 0.055 Uiso d 1 . .
    S S2 -0.24072(14) 0.17401(9) -0.08375(12) 0.0386(4) Uani d 1 . .
    C C23 0.7409(6) 0.2901(4) 0.3641(5) 0.0358(13) Uani d 1 . .
    C C24 0.5781(6) 0.2738(4) 0.3122(5) 0.0392(14) Uani d 1 . .
    H H24 0.5076 0.2871 0.3621 0.047 Uiso calc 1 . .
    C C25 0.5242(6) 0.2420(4) 0.2013(5) 0.0380(13) Uani d 1 . .
    H H25 0.5942 0.2310 0.1502 0.046 Uiso calc 1 . .
    C C26 0.3622(6) 0.2223(4) 0.1512(5) 0.0371(14) Uani d 1 . .
    O O1 0.7763(4) 0.3234(3) 0.4689(3) 0.0469(10) Uani d 1 . .
    O O2 0.8346(4) 0.2695(3) 0.2995(3) 0.0591(12) Uani d 1 . .
    O O3 0.3301(4) 0.1922(3) 0.0429(3) 0.0473(11) Uani d 1 . .
    O O4 0.2689(4) 0.2349(4) 0.2157(3) 0.0642(14) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.344(7) ?
    C1 C2 . 1.514(7) ?
    C1 S1 . 1.744(5) ?
    C2 C3A . 1.520(9) ?
    C2 C8 . 1.524(8) ?
    C2 C9 . 1.551(9) ?
    C2 C3B . 1.66(3) ?
    C3A C4A . 1.541(14) ?
    C3A H3A1 . 0.9900 ?
    C3A H3A2 . 0.9900 ?
    C4A C5 . 1.575(10) ?
    C4A H4A1 . 0.9900 ?
    C4A H4A2 . 0.9900 ?
    C3B C4B . 1.53(5) ?
    C3B H3B1 . 0.9900 ?
    C3B H3B2 . 0.9900 ?
    C4B C5 . 1.47(2) ?
    C4B H4B1 . 0.9900 ?
    C4B H4B2 . 0.9900 ?
    C5 C6 . 1.504(7) ?
    C5 C10 . 1.526(8) ?
    C5 C11 . 1.540(8) ?
    C6 N1 . 1.401(6) ?
    C7 N2 . 1.318(6) ?
    C7 N1 . 1.325(6) ?
    C7 S1 . 1.721(5) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    N1 H1N . 0.85(5) ?
    N2 H2N . 0.94(6) ?
    N2 H3N . 0.91(6) ?
    C12 C17 . 1.345(7) ?
    C12 C13 . 1.496(7) ?
    C12 S2 . 1.761(5) ?
    C13 C19 . 1.527(8) ?
    C13 C14 . 1.532(7) ?
    C13 C20 . 1.533(8) ?
    C14 C15 . 1.526(8) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.542(7) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.513(7) ?
    C16 C22 . 1.523(7) ?
    C16 C21 . 1.536(7) ?
    C17 N3 . 1.404(6) ?
    C18 N4 . 1.319(7) ?
    C18 N3 . 1.320(6) ?
    C18 S2 . 1.723(5) ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    N3 H4N . 0.96(5) ?
    N4 H5N . 1.00(6) ?
    N4 H6N . 0.81(6) ?
    C23 O1 . 1.251(6) ?
    C23 O2 . 1.258(6) ?
    C23 C24 . 1.484(7) ?
    C24 C25 . 1.321(6) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.483(7) ?
    C25 H25 . 0.9500 ?
    C26 O4 . 1.232(6) ?
    C26 O3 . 1.267(6) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 126.7(5) ?
    C6 C1 S1 . . 111.2(4) ?
    C2 C1 S1 . . 122.1(4) ?
    C1 C2 C3A . . 106.1(5) ?
    C1 C2 C8 . . 109.5(5) ?
    C3A C2 C8 . . 118.0(6) ?
    C1 C2 C9 . . 109.7(5) ?
    C3A C2 C9 . . 105.5(6) ?
    C8 C2 C9 . . 107.7(5) ?
    C1 C2 C3B . . 102.3(11) ?
    C8 C2 C3B . . 89.8(15) ?
    C9 C2 C3B . . 134.9(15) ?
    C2 C3A C4A . . 111.1(9) ?
    C2 C3A H3A1 . . 109.4 ?
    C4A C3A H3A1 . . 109.4 ?
    C2 C3A H3A2 . . 109.4 ?
    C4A C3A H3A2 . . 109.4 ?
    H3A1 C3A H3A2 . . 108.0 ?
    C3A C4A C5 . . 111.7(8) ?
    C3A C4A H4A1 . . 109.3 ?
    C5 C4A H4A1 . . 109.3 ?
    C3A C4A H4A2 . . 109.3 ?
    C5 C4A H4A2 . . 109.3 ?
    H4A1 C4A H4A2 . . 107.9 ?
    C4B C3B C2 . . 114(3) ?
    C4B C3B H3B1 . . 108.7 ?
    C2 C3B H3B1 . . 108.7 ?
    C4B C3B H3B2 . . 108.7 ?
    C2 C3B H3B2 . . 108.7 ?
    H3B1 C3B H3B2 . . 107.6 ?
    C5 C4B C3B . . 112(3) ?
    C5 C4B H4B1 . . 109.3 ?
    C3B C4B H4B1 . . 109.3 ?
    C5 C4B H4B2 . . 109.3 ?
    C3B C4B H4B2 . . 109.3 ?
    H4B1 C4B H4B2 . . 107.9 ?
    C4B C5 C6 . . 112.1(10) ?
    C4B C5 C10 . . 121.4(12) ?
    C6 C5 C10 . . 110.5(5) ?
    C4B C5 C11 . . 92.1(15) ?
    C6 C5 C11 . . 110.1(4) ?
    C10 C5 C11 . . 108.9(5) ?
    C6 C5 C4A . . 105.1(5) ?
    C10 C5 C4A . . 106.4(5) ?
    C11 C5 C4A . . 115.8(6) ?
    C1 C6 N1 . . 112.5(4) ?
    C1 C6 C5 . . 126.0(4) ?
    N1 C6 C5 . . 121.5(4) ?
    N2 C7 N1 . . 123.7(5) ?
    N2 C7 S1 . . 124.4(4) ?
    N1 C7 S1 . . 111.8(4) ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C5 C11 H11A . . 109.5 ?
    C5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 N1 C6 . . 114.1(4) ?
    C7 N1 H1N . . 119(3) ?
    C6 N1 H1N . . 126(3) ?
    C7 N2 H2N . . 117(4) ?
    C7 N2 H3N . . 119(4) ?
    H2N N2 H3N . . 118(5) ?
    C7 S1 C1 . . 90.3(2) ?
    C17 C12 C13 . . 127.0(5) ?
    C17 C12 S2 . . 110.0(4) ?
    C13 C12 S2 . . 122.9(4) ?
    C12 C13 C19 . . 110.8(5) ?
    C12 C13 C14 . . 106.9(4) ?
    C19 C13 C14 . . 111.1(5) ?
    C12 C13 C20 . . 110.9(5) ?
    C19 C13 C20 . . 108.2(5) ?
    C14 C13 C20 . . 108.8(5) ?
    C15 C14 C13 . . 113.0(5) ?
    C15 C14 H14A . . 109.0 ?
    C13 C14 H14A . . 109.0 ?
    C15 C14 H14B . . 109.0 ?
    C13 C14 H14B . . 109.0 ?
    H14A C14 H14B . . 107.8 ?
    C14 C15 C16 . . 114.5(5) ?
    C14 C15 H15A . . 108.6 ?
    C16 C15 H15A . . 108.6 ?
    C14 C15 H15B . . 108.6 ?
    C16 C15 H15B . . 108.6 ?
    H15A C15 H15B . . 107.6 ?
    C17 C16 C22 . . 109.7(4) ?
    C17 C16 C21 . . 110.2(4) ?
    C22 C16 C21 . . 109.8(5) ?
    C17 C16 C15 . . 106.8(4) ?
    C22 C16 C15 . . 111.4(4) ?
    C21 C16 C15 . . 108.9(5) ?
    C12 C17 N3 . . 113.5(4) ?
    C12 C17 C16 . . 125.6(4) ?
    N3 C17 C16 . . 120.9(4) ?
    N4 C18 N3 . . 122.9(5) ?
    N4 C18 S2 . . 124.9(4) ?
    N3 C18 S2 . . 112.1(4) ?
    C13 C19 H19A . . 109.5 ?
    C13 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C13 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C13 C20 H20A . . 109.5 ?
    C13 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C13 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C16 C21 H21A . . 109.5 ?
    C16 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C16 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C16 C22 H22A . . 109.5 ?
    C16 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C16 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C18 N3 C17 . . 113.9(4) ?
    C18 N3 H4N . . 123(3) ?
    C17 N3 H4N . . 123(3) ?
    C18 N4 H5N . . 112(3) ?
    C18 N4 H6N . . 115(4) ?
    H5N N4 H6N . . 130(5) ?
    C18 S2 C12 . . 90.5(2) ?
    O1 C23 O2 . . 124.2(5) ?
    O1 C23 C24 . . 118.1(5) ?
    O2 C23 C24 . . 117.7(5) ?
    C25 C24 C23 . . 124.6(5) ?
    C25 C24 H24 . . 117.7 ?
    C23 C24 H24 . . 117.7 ?
    C24 C25 C26 . . 124.6(5) ?
    C24 C25 H25 . . 117.7 ?
    C26 C25 H25 . . 117.7 ?
    O4 C26 O3 . . 124.4(5) ?
    O4 C26 C25 . . 119.2(5) ?
    O3 C26 C25 . . 116.3(5) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3A . . . . -15.4(9) ?
    S1 C1 C2 C3A . . . . 165.0(6) ?
    C6 C1 C2 C8 . . . . 113.1(6) ?
    S1 C1 C2 C8 . . . . -66.6(6) ?
    C6 C1 C2 C9 . . . . -128.9(6) ?
    S1 C1 C2 C9 . . . . 51.4(6) ?
    C6 C1 C2 C3B . . . . 18.8(17) ?
    S1 C1 C2 C3B . . . . -160.8(16) ?
    C1 C2 C3A C4A . . . . 47.8(10) ?
    C8 C2 C3A C4A . . . . -75.5(9) ?
    C9 C2 C3A C4A . . . . 164.1(8) ?
    C2 C3A C4A C5 . . . . -69.2(12) ?
    C1 C2 C3B C4B . . . . -48(3) ?
    C8 C2 C3B C4B . . . . -158(3) ?
    C9 C2 C3B C4B . . . . 87(3) ?
    C2 C3B C4B C5 . . . . 62(4) ?
    C3B C4B C5 C6 . . . . -38(3) ?
    C3B C4B C5 C10 . . . . 95(3) ?
    C3B C4B C5 C11 . . . . -151(3) ?
    C3A C4A C5 C6 . . . . 47.3(10) ?
    C3A C4A C5 C10 . . . . 164.5(8) ?
    C3A C4A C5 C11 . . . . -74.4(10) ?
    C2 C1 C6 N1 . . . . 179.6(5) ?
    S1 C1 C6 N1 . . . . -0.7(5) ?
    C2 C1 C6 C5 . . . . -0.9(9) ?
    S1 C1 C6 C5 . . . . 178.8(4) ?
    C4B C5 C6 C1 . . . . 9.7(17) ?
    C10 C5 C6 C1 . . . . -129.1(5) ?
    C11 C5 C6 C1 . . . . 110.6(6) ?
    C4A C5 C6 C1 . . . . -14.7(8) ?
    C4B C5 C6 N1 . . . . -170.9(16) ?
    C10 C5 C6 N1 . . . . 50.4(6) ?
    C11 C5 C6 N1 . . . . -69.9(6) ?
    C4A C5 C6 N1 . . . . 164.7(6) ?
    N2 C7 N1 C6 . . . . 177.7(5) ?
    S1 C7 N1 C6 . . . . 0.3(6) ?
    C1 C6 N1 C7 . . . . 0.3(6) ?
    C5 C6 N1 C7 . . . . -179.2(5) ?
    N2 C7 S1 C1 . . . . -177.9(5) ?
    N1 C7 S1 C1 . . . . -0.6(4) ?
    C6 C1 S1 C7 . . . . 0.8(4) ?
    C2 C1 S1 C7 . . . . -179.5(5) ?
    C17 C12 C13 C19 . . . . 107.5(6) ?
    S2 C12 C13 C19 . . . . -75.3(6) ?
    C17 C12 C13 C14 . . . . -13.7(7) ?
    S2 C12 C13 C14 . . . . 163.5(4) ?
    C17 C12 C13 C20 . . . . -132.2(6) ?
    S2 C12 C13 C20 . . . . 45.0(6) ?
    C12 C13 C14 C15 . . . . 44.1(6) ?
    C19 C13 C14 C15 . . . . -77.0(6) ?
    C20 C13 C14 C15 . . . . 163.9(5) ?
    C13 C14 C15 C16 . . . . -62.5(7) ?
    C14 C15 C16 C17 . . . . 40.9(6) ?
    C14 C15 C16 C22 . . . . -78.9(6) ?
    C14 C15 C16 C21 . . . . 159.9(5) ?
    C13 C12 C17 N3 . . . . 176.7(5) ?
    S2 C12 C17 N3 . . . . -0.8(6) ?
    C13 C12 C17 C16 . . . . -3.4(8) ?
    S2 C12 C17 C16 . . . . 179.1(4) ?
    C22 C16 C17 C12 . . . . 111.1(6) ?
    C21 C16 C17 C12 . . . . -127.9(5) ?
    C15 C16 C17 C12 . . . . -9.8(7) ?
    C22 C16 C17 N3 . . . . -69.1(6) ?
    C21 C16 C17 N3 . . . . 51.9(6) ?
    C15 C16 C17 N3 . . . . 170.1(5) ?
    N4 C18 N3 C17 . . . . -178.6(5) ?
    S2 C18 N3 C17 . . . . -1.4(6) ?
    C12 C17 N3 C18 . . . . 1.5(6) ?
    C16 C17 N3 C18 . . . . -178.4(4) ?
    N4 C18 S2 C12 . . . . 177.9(5) ?
    N3 C18 S2 C12 . . . . 0.8(4) ?
    C17 C12 S2 C18 . . . . 0.0(4) ?
    C13 C12 S2 C18 . . . . -177.6(4) ?
    O1 C23 C24 C25 . . . . 177.5(5) ?
    O2 C23 C24 C25 . . . . -2.4(8) ?
    C23 C24 C25 C26 . . . . 177.5(5) ?
    C24 C25 C26 O4 . . . . -0.8(8) ?
    C24 C25 C26 O3 . . . . 179.9(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1N O1 . 0.85(5) 1.84(5) 2.670(5) 167(5)
    N2 H2N O2 . 0.94(6) 1.77(6) 2.704(6) 177(5)
    N2 H3N O4 1_655 0.91(6) 1.90(6) 2.746(6) 153(5)
    N3 H4N O3 . 0.96(5) 1.67(5) 2.617(5) 169(5)
    N4 H5N O4 . 1.00(6) 1.75(6) 2.754(7) 178(5)
    N4 H6N O2 1_455 0.81(6) 2.09(6) 2.763(6) 141(6)
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.968
_shelx_estimated_absorpt_T_max     0.996
data_V
_database_code_depnum_ccdc_archive 'CCDC 1886885'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;\
Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate--2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-\
benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety
      '1.5(C11 H19 N2 S ), 0.5(C4 H4 O4 2-), 0.5(C4 H5 O4 -), 0.5(C11 H18 N2 S)'
_chemical_formula_sum     'C26 H42 N4 O4 S2'
_chemical_formula_iupac
             '1.5C11 H19 N2 S +, 0.5C4 H4 O4 2-, 0.5C4 H5 O4 -, 0.5C11 H18 N2 S'
_chemical_formula_weight     538.75
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.9437(3)
_cell_length_b     14.7253(4)
_cell_length_c     11.2676(4)
_cell_angle_alpha     90
_cell_angle_beta     100.493(3)
_cell_angle_gamma     90
_cell_volume     1459.11(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9613
_cell_measurement_theta_min     2.3030
_cell_measurement_theta_max     27.9760
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.320
_exptl_crystal_size_mid     0.150
_exptl_crystal_size_min     0.020
_exptl_crystal_density_diffrn     1.226
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     580
_exptl_absorpt_coefficient_mu     0.219
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2017)
;
_exptl_absorpt_correction_T_min     0.77888
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     173(2)
_diffrn_source     'rotating anode'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device_type     ' Rigaku XtaLAB P200 HPC '
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19079
_diffrn_reflns_av_R_equivalents     0.0342
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_theta_min     2.300
_diffrn_reflns_theta_max     29.116
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.852
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     6272
_reflns_number_gt     5511
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0466
_refine_ls_R_factor_gt     0.0391
_refine_ls_wR_factor_gt     0.0906
_refine_ls_wR_factor_ref     0.0939
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     6272
_refine_ls_number_parameters     354
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0529P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.255
_refine_diff_density_min     -0.247
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack  x determined using 2211
quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     0.00(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrystalClear-SM (Rigaku,  2017)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku, 2017)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 1.2888(3) 0.39542(19) 0.6860(2) 0.0263(6) Uani d 1 . .
    C C2 1.3946(3) 0.4407(2) 0.7881(3) 0.0357(7) Uani d 1 . .
    C C3A 1.2962(6) 0.5069(4) 0.8461(5) 0.0365(17) Uiso d 0.593(11) A 1
    H H3A1 1.2689 0.5598 0.7923 0.044 Uiso calc 0.593(11) A 1
    H H3A2 1.3548 0.5293 0.9237 0.044 Uiso calc 0.593(11) A 1
    C C4A 1.1500(6) 0.4594(5) 0.8685(6) 0.0366(16) Uiso d 0.593(11) A 1
    H H4A1 1.0979 0.4985 0.9198 0.044 Uiso calc 0.593(11) A 1
    H H4A2 1.1768 0.4015 0.9118 0.044 Uiso calc 0.593(11) A 1
    C C3B 1.2917(10) 0.4598(8) 0.8865(9) 0.049(3) Uiso d 0.407(11) A 2
    H H3B1 1.2754 0.4020 0.9271 0.059 Uiso calc 0.407(11) A 2
    H H3B2 1.3468 0.5015 0.9483 0.059 Uiso calc 0.407(11) A 2
    C C4B 1.1399(9) 0.5005(7) 0.8353(8) 0.038(2) Uiso d 0.407(11) A 2
    H H4B1 1.1564 0.5586 0.7954 0.046 Uiso calc 0.407(11) A 2
    H H4B2 1.0860 0.5143 0.9025 0.046 Uiso calc 0.407(11) A 2
    C C5 1.0393(3) 0.4400(2) 0.7449(3) 0.0308(6) Uani d 1 . .
    C C6 1.1354(3) 0.39467(18) 0.6659(2) 0.0236(6) Uani d 1 . .
    C C7 1.1723(3) 0.30960(19) 0.5050(2) 0.0265(6) Uani d 1 . .
    C C8 1.4933(5) 0.3708(3) 0.8639(4) 0.0612(11) Uani d 1 . .
    H H8A 1.5574 0.4010 0.9324 0.092 Uiso calc 1 . .
    H H8B 1.5579 0.3404 0.8146 0.092 Uiso calc 1 . .
    H H8C 1.4285 0.3258 0.8939 0.092 Uiso calc 1 . .
    C C9 1.5000(5) 0.5061(3) 0.7370(4) 0.0690(12) Uani d 1 . .
    H H9A 1.5592 0.5414 0.8030 0.103 Uiso calc 1 . .
    H H9B 1.4390 0.5474 0.6793 0.103 Uiso calc 1 . .
    H H9C 1.5691 0.4714 0.6961 0.103 Uiso calc 1 . .
    C C10 0.9296(4) 0.3719(2) 0.7834(3) 0.0480(9) Uani d 1 . .
    H H10A 0.8715 0.4014 0.8385 0.072 Uiso calc 1 . .
    H H10B 0.9869 0.3207 0.8245 0.072 Uiso calc 1 . .
    H H10C 0.8596 0.3499 0.7121 0.072 Uiso calc 1 . .
    C C11 0.9468(5) 0.5170(3) 0.6769(4) 0.0669(13) Uani d 1 . .
    H H11A 0.8820 0.5444 0.7285 0.100 Uiso calc 1 . .
    H H11B 0.8830 0.4928 0.6036 0.100 Uiso calc 1 . .
    H H11C 1.0158 0.5631 0.6547 0.100 Uiso calc 1 . .
    N N1 1.0710(3) 0.34631(16) 0.5629(2) 0.0246(5) Uani d 1 . .
    H H1N 0.968(4) 0.335(2) 0.534(3) 0.030 Uiso d 1 . .
    N N2 1.1368(3) 0.2592(2) 0.4072(2) 0.0397(7) Uani d 1 . .
    H H2N 1.209(4) 0.241(3) 0.369(3) 0.048 Uiso d 1 . .
    H H3N 1.047(4) 0.257(3) 0.374(3) 0.048 Uiso d 1 . .
    S S1 1.35670(7) 0.33342(5) 0.57387(6) 0.03090(18) Uani d 1 . .
    C C12 -0.1518(3) 0.11232(19) -0.1824(3) 0.0261(6) Uani d 1 . .
    C C13 -0.2459(4) 0.0700(2) -0.2927(3) 0.0345(7) Uani d 1 . .
    C C14 -0.1355(4) 0.0472(2) -0.3784(3) 0.0405(8) Uani d 1 . .
    H H14A -0.1871 0.0066 -0.4431 0.049 Uiso calc 1 . .
    H H14B -0.1081 0.1038 -0.4167 0.049 Uiso calc 1 . .
    C C15 0.0097(4) 0.0011(2) -0.3133(3) 0.0426(8) Uani d 1 . .
    H H15A 0.0715 -0.0172 -0.3738 0.051 Uiso calc 1 . .
    H H15B -0.0183 -0.0547 -0.2736 0.051 Uiso calc 1 . .
    C C16 0.1071(3) 0.06150(19) -0.2180(3) 0.0295(6) Uani d 1 . .
    C C17 0.0007(3) 0.11035(18) -0.1495(2) 0.0245(6) Uani d 1 . .
    C C18 -0.0513(3) 0.19535(18) 0.0048(2) 0.0263(6) Uani d 1 . .
    C C19 -0.3270(5) -0.0149(3) -0.2585(4) 0.0581(10) Uani d 1 . .
    H H19A -0.3866 -0.0421 -0.3315 0.087 Uiso calc 1 . .
    H H19B -0.3950 0.0018 -0.2030 0.087 Uiso calc 1 . .
    H H19C -0.2516 -0.0588 -0.2193 0.087 Uiso calc 1 . .
    C C20 -0.3652(4) 0.1381(2) -0.3552(3) 0.0459(8) Uani d 1 . .
    H H20A -0.4216 0.1112 -0.4295 0.069 Uiso calc 1 . .
    H H20B -0.3141 0.1936 -0.3748 0.069 Uiso calc 1 . .
    H H20C -0.4358 0.1530 -0.3010 0.069 Uiso calc 1 . .
    C C21 0.2173(4) 0.0007(2) -0.1322(3) 0.0446(8) Uani d 1 . .
    H H21A 0.2785 -0.0351 -0.1789 0.067 Uiso calc 1 . .
    H H21B 0.1593 -0.0401 -0.0890 0.067 Uiso calc 1 . .
    H H21C 0.2844 0.0388 -0.0739 0.067 Uiso calc 1 . .
    C C22 0.1982(4) 0.1307(2) -0.2773(3) 0.0426(8) Uani d 1 . .
    H H22A 0.2681 0.0986 -0.3203 0.064 Uiso calc 1 . .
    H H22B 0.2564 0.1697 -0.2150 0.064 Uiso calc 1 . .
    H H22C 0.1283 0.1680 -0.3344 0.064 Uiso calc 1 . .
    N N3 0.0575(3) 0.15834(16) -0.0442(2) 0.0248(5) Uani d 1 . .
    H H4N 0.153(9) 0.165(5) -0.011(6) 0.030 Uiso d 0.50(5) . .
    N N4 -0.0255(3) 0.2469(2) 0.1041(2) 0.0387(7) Uani d 1 . .
    H H5N -0.096(4) 0.249(3) 0.142(3) 0.046 Uiso d 1 . .
    H H6N 0.073(4) 0.245(2) 0.147(3) 0.046 Uiso d 1 . .
    S S2 -0.23122(8) 0.17442(5) -0.07649(6) 0.02918(18) Uani d 1 . .
    C C26 0.3743(3) 0.22426(19) 0.1462(3) 0.0271(6) Uani d 1 . .
    C C25 0.5352(3) 0.2536(2) 0.1889(3) 0.0298(6) Uani d 1 . .
    H H25A 0.5538 0.3096 0.1451 0.036 Uiso calc 1 . .
    H H25B 0.6039 0.2060 0.1676 0.036 Uiso calc 1 . .
    C C24 0.5760(3) 0.2717(2) 0.3238(3) 0.0300(7) Uani d 1 . .
    H H24A 0.5202 0.3264 0.3427 0.036 Uiso calc 1 . .
    H H24B 0.5406 0.2199 0.3672 0.036 Uiso calc 1 . .
    C C23 0.7441(3) 0.2859(2) 0.3709(3) 0.0284(6) Uani d 1 . .
    O O1 0.7810(2) 0.32184(16) 0.47272(18) 0.0379(5) Uani d 1 . .
    O O2 0.8363(2) 0.2585(2) 0.3079(2) 0.0575(7) Uani d 1 . .
    O O3 0.3395(3) 0.20074(16) 0.03486(19) 0.0388(6) Uani d 1 . .
    H H1O 0.249(11) 0.191(5) 0.008(7) 0.047 Uiso d 0.50(5) . .
    O O4 0.2832(2) 0.2213(2) 0.21545(19) 0.0500(7) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.349(4) ?
    C1 C2 . 1.506(4) ?
    C1 S1 . 1.754(3) ?
    C2 C8 . 1.515(5) ?
    C2 C9 . 1.531(5) ?
    C2 C3A . 1.537(6) ?
    C2 C3B . 1.589(10) ?
    C3A C4A . 1.544(9) ?
    C3A H3A1 . 0.9900 ?
    C3A H3A2 . 0.9900 ?
    C4A C5 . 1.581(6) ?
    C4A H4A1 . 0.9900 ?
    C4A H4A2 . 0.9900 ?
    C3B C4B . 1.499(14) ?
    C3B H3B1 . 0.9900 ?
    C3B H3B2 . 0.9900 ?
    C4B C5 . 1.519(8) ?
    C4B H4B1 . 0.9900 ?
    C4B H4B2 . 0.9900 ?
    C5 C6 . 1.502(4) ?
    C5 C10 . 1.520(4) ?
    C5 C11 . 1.525(5) ?
    C6 N1 . 1.394(3) ?
    C7 N2 . 1.319(4) ?
    C7 N1 . 1.325(3) ?
    C7 S1 . 1.726(3) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    N1 H1N . 0.93(3) ?
    N2 H2N . 0.89(4) ?
    N2 H3N . 0.82(4) ?
    C12 C17 . 1.348(4) ?
    C12 C13 . 1.503(4) ?
    C12 S2 . 1.753(3) ?
    C13 C19 . 1.530(4) ?
    C13 C20 . 1.538(5) ?
    C13 C14 . 1.538(4) ?
    C14 C15 . 1.528(5) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.536(4) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.512(4) ?
    C16 C22 . 1.532(4) ?
    C16 C21 . 1.536(4) ?
    C17 N3 . 1.395(4) ?
    C18 N3 . 1.321(3) ?
    C18 N4 . 1.337(4) ?
    C18 S2 . 1.728(3) ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    N3 H4N . 0.87(8) ?
    N4 H5N . 0.82(4) ?
    N4 H6N . 0.92(4) ?
    C26 O4 . 1.228(3) ?
    C26 O3 . 1.283(4) ?
    C26 C25 . 1.496(4) ?
    C25 C24 . 1.521(4) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C24 C23 . 1.515(4) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C23 O2 . 1.249(4) ?
    C23 O1 . 1.252(3) ?
    O3 H1O . 0.82(10) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 127.6(3) ?
    C6 C1 S1 . . 110.5(2) ?
    C2 C1 S1 . . 122.0(2) ?
    C1 C2 C8 . . 110.5(3) ?
    C1 C2 C9 . . 109.6(3) ?
    C8 C2 C9 . . 107.7(3) ?
    C1 C2 C3A . . 106.1(3) ?
    C8 C2 C3A . . 120.8(4) ?
    C9 C2 C3A . . 101.6(4) ?
    C1 C2 C3B . . 104.4(4) ?
    C8 C2 C3B . . 94.5(5) ?
    C9 C2 C3B . . 128.7(5) ?
    C2 C3A C4A . . 110.5(5) ?
    C2 C3A H3A1 . . 109.6 ?
    C4A C3A H3A1 . . 109.6 ?
    C2 C3A H3A2 . . 109.6 ?
    C4A C3A H3A2 . . 109.6 ?
    H3A1 C3A H3A2 . . 108.1 ?
    C3A C4A C5 . . 110.5(5) ?
    C3A C4A H4A1 . . 109.5 ?
    C5 C4A H4A1 . . 109.5 ?
    C3A C4A H4A2 . . 109.5 ?
    C5 C4A H4A2 . . 109.5 ?
    H4A1 C4A H4A2 . . 108.1 ?
    C4B C3B C2 . . 113.6(8) ?
    C4B C3B H3B1 . . 108.8 ?
    C2 C3B H3B1 . . 108.8 ?
    C4B C3B H3B2 . . 108.8 ?
    C2 C3B H3B2 . . 108.8 ?
    H3B1 C3B H3B2 . . 107.7 ?
    C3B C4B C5 . . 114.1(8) ?
    C3B C4B H4B1 . . 108.7 ?
    C5 C4B H4B1 . . 108.7 ?
    C3B C4B H4B2 . . 108.7 ?
    C5 C4B H4B2 . . 108.7 ?
    H4B1 C4B H4B2 . . 107.6 ?
    C6 C5 C4B . . 109.0(4) ?
    C6 C5 C10 . . 110.2(2) ?
    C4B C5 C10 . . 122.0(4) ?
    C6 C5 C11 . . 110.4(3) ?
    C4B C5 C11 . . 95.9(5) ?
    C10 C5 C11 . . 108.3(3) ?
    C6 C5 C4A . . 105.6(3) ?
    C10 C5 C4A . . 101.6(3) ?
    C11 C5 C4A . . 120.2(4) ?
    C1 C6 N1 . . 113.4(2) ?
    C1 C6 C5 . . 124.8(3) ?
    N1 C6 C5 . . 121.7(2) ?
    N2 C7 N1 . . 124.0(3) ?
    N2 C7 S1 . . 123.7(2) ?
    N1 C7 S1 . . 112.3(2) ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C5 C11 H11A . . 109.5 ?
    C5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 N1 C6 . . 113.7(2) ?
    C7 N1 H1N . . 118.6(18) ?
    C6 N1 H1N . . 127.6(18) ?
    C7 N2 H2N . . 120(2) ?
    C7 N2 H3N . . 117(3) ?
    H2N N2 H3N . . 121(4) ?
    C7 S1 C1 . . 90.11(13) ?
    C17 C12 C13 . . 127.2(3) ?
    C17 C12 S2 . . 109.8(2) ?
    C13 C12 S2 . . 123.0(2) ?
    C12 C13 C19 . . 110.5(3) ?
    C12 C13 C20 . . 110.2(3) ?
    C19 C13 C20 . . 109.1(3) ?
    C12 C13 C14 . . 106.4(2) ?
    C19 C13 C14 . . 111.6(3) ?
    C20 C13 C14 . . 109.1(3) ?
    C15 C14 C13 . . 112.5(3) ?
    C15 C14 H14A . . 109.1 ?
    C13 C14 H14A . . 109.1 ?
    C15 C14 H14B . . 109.1 ?
    C13 C14 H14B . . 109.1 ?
    H14A C14 H14B . . 107.8 ?
    C14 C15 C16 . . 113.7(3) ?
    C14 C15 H15A . . 108.8 ?
    C16 C15 H15A . . 108.8 ?
    C14 C15 H15B . . 108.8 ?
    C16 C15 H15B . . 108.8 ?
    H15A C15 H15B . . 107.7 ?
    C17 C16 C22 . . 109.9(2) ?
    C17 C16 C21 . . 110.3(2) ?
    C22 C16 C21 . . 109.3(3) ?
    C17 C16 C15 . . 107.6(2) ?
    C22 C16 C15 . . 111.0(3) ?
    C21 C16 C15 . . 108.7(3) ?
    C12 C17 N3 . . 114.6(2) ?
    C12 C17 C16 . . 124.7(2) ?
    N3 C17 C16 . . 120.7(2) ?
    N3 C18 N4 . . 123.8(3) ?
    N3 C18 S2 . . 113.0(2) ?
    N4 C18 S2 . . 123.2(2) ?
    C13 C19 H19A . . 109.5 ?
    C13 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C13 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C13 C20 H20A . . 109.5 ?
    C13 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C13 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C16 C21 H21A . . 109.5 ?
    C16 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C16 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C16 C22 H22A . . 109.5 ?
    C16 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C16 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C18 N3 C17 . . 112.5(2) ?
    C18 N3 H4N . . 121(4) ?
    C17 N3 H4N . . 127(4) ?
    C18 N4 H5N . . 115(3) ?
    C18 N4 H6N . . 115(2) ?
    H5N N4 H6N . . 118(3) ?
    C18 S2 C12 . . 90.03(13) ?
    O4 C26 O3 . . 122.7(3) ?
    O4 C26 C25 . . 121.1(3) ?
    O3 C26 C25 . . 116.1(2) ?
    C26 C25 C24 . . 114.4(2) ?
    C26 C25 H25A . . 108.7 ?
    C24 C25 H25A . . 108.7 ?
    C26 C25 H25B . . 108.7 ?
    C24 C25 H25B . . 108.7 ?
    H25A C25 H25B . . 107.6 ?
    C23 C24 C25 . . 114.6(2) ?
    C23 C24 H24A . . 108.6 ?
    C25 C24 H24A . . 108.6 ?
    C23 C24 H24B . . 108.6 ?
    C25 C24 H24B . . 108.6 ?
    H24A C24 H24B . . 107.6 ?
    O2 C23 O1 . . 124.5(3) ?
    O2 C23 C24 . . 118.2(2) ?
    O1 C23 C24 . . 117.3(2) ?
    C26 O3 H1O . . 117(5) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C8 . . . . 117.8(4) ?
    S1 C1 C2 C8 . . . . -61.8(3) ?
    C6 C1 C2 C9 . . . . -123.7(3) ?
    S1 C1 C2 C9 . . . . 56.7(3) ?
    C6 C1 C2 C3A . . . . -14.8(5) ?
    S1 C1 C2 C3A . . . . 165.7(3) ?
    C6 C1 C2 C3B . . . . 17.2(6) ?
    S1 C1 C2 C3B . . . . -162.3(5) ?
    C1 C2 C3A C4A . . . . 47.7(6) ?
    C8 C2 C3A C4A . . . . -78.9(5) ?
    C9 C2 C3A C4A . . . . 162.2(5) ?
    C2 C3A C4A C5 . . . . -70.2(6) ?
    C1 C2 C3B C4B . . . . -46.1(9) ?
    C8 C2 C3B C4B . . . . -158.7(8) ?
    C9 C2 C3B C4B . . . . 84.4(9) ?
    C2 C3B C4B C5 . . . . 62.4(12) ?
    C3B C4B C5 C6 . . . . -40.4(10) ?
    C3B C4B C5 C10 . . . . 89.8(8) ?
    C3B C4B C5 C11 . . . . -154.4(8) ?
    C3A C4A C5 C6 . . . . 49.7(6) ?
    C3A C4A C5 C10 . . . . 164.7(5) ?
    C3A C4A C5 C11 . . . . -75.9(5) ?
    C2 C1 C6 N1 . . . . -179.9(3) ?
    S1 C1 C6 N1 . . . . -0.4(3) ?
    C2 C1 C6 C5 . . . . -0.4(5) ?
    S1 C1 C6 C5 . . . . 179.2(2) ?
    C4B C5 C6 C1 . . . . 10.6(6) ?
    C10 C5 C6 C1 . . . . -125.7(3) ?
    C11 C5 C6 C1 . . . . 114.7(3) ?
    C4A C5 C6 C1 . . . . -16.8(4) ?
    C4B C5 C6 N1 . . . . -169.9(5) ?
    C10 C5 C6 N1 . . . . 53.8(4) ?
    C11 C5 C6 N1 . . . . -65.8(4) ?
    C4A C5 C6 N1 . . . . 162.8(4) ?
    N2 C7 N1 C6 . . . . 178.3(3) ?
    S1 C7 N1 C6 . . . . -0.5(3) ?
    C1 C6 N1 C7 . . . . 0.6(3) ?
    C5 C6 N1 C7 . . . . -179.0(2) ?
    N2 C7 S1 C1 . . . . -178.5(3) ?
    N1 C7 S1 C1 . . . . 0.3(2) ?
    C6 C1 S1 C7 . . . . 0.1(2) ?
    C2 C1 S1 C7 . . . . 179.7(2) ?
    C17 C12 C13 C19 . . . . 105.9(4) ?
    S2 C12 C13 C19 . . . . -74.9(3) ?
    C17 C12 C13 C20 . . . . -133.5(3) ?
    S2 C12 C13 C20 . . . . 45.7(3) ?
    C17 C12 C13 C14 . . . . -15.3(4) ?
    S2 C12 C13 C14 . . . . 163.9(2) ?
    C12 C13 C14 C15 . . . . 45.6(3) ?
    C19 C13 C14 C15 . . . . -74.9(3) ?
    C20 C13 C14 C15 . . . . 164.5(3) ?
    C13 C14 C15 C16 . . . . -63.9(4) ?
    C14 C15 C16 C17 . . . . 42.2(3) ?
    C14 C15 C16 C22 . . . . -78.1(3) ?
    C14 C15 C16 C21 . . . . 161.6(3) ?
    C13 C12 C17 N3 . . . . 177.9(3) ?
    S2 C12 C17 N3 . . . . -1.4(3) ?
    C13 C12 C17 C16 . . . . -1.9(4) ?
    S2 C12 C17 C16 . . . . 178.8(2) ?
    C22 C16 C17 C12 . . . . 110.0(3) ?
    C21 C16 C17 C12 . . . . -129.4(3) ?
    C15 C16 C17 C12 . . . . -11.0(4) ?
    C22 C16 C17 N3 . . . . -69.8(3) ?
    C21 C16 C17 N3 . . . . 50.8(3) ?
    C15 C16 C17 N3 . . . . 169.2(3) ?
    N4 C18 N3 C17 . . . . -177.9(3) ?
    S2 C18 N3 C17 . . . . -0.6(3) ?
    C12 C17 N3 C18 . . . . 1.3(3) ?
    C16 C17 N3 C18 . . . . -178.9(2) ?
    N3 C18 S2 C12 . . . . -0.2(2) ?
    N4 C18 S2 C12 . . . . 177.2(3) ?
    C17 C12 S2 C18 . . . . 0.9(2) ?
    C13 C12 S2 C18 . . . . -178.4(2) ?
    O4 C26 C25 C24 . . . . 4.3(4) ?
    O3 C26 C25 C24 . . . . -174.1(3) ?
    C26 C25 C24 C23 . . . . 170.2(3) ?
    C25 C24 C23 O2 . . . . -18.9(4) ?
    C25 C24 C23 O1 . . . . 163.5(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1N O1 . 0.93(3) 1.70(3) 2.632(3) 175(3)
    N2 H2N O4 1_655 0.89(4) 1.98(4) 2.779(3) 149(3)
    N2 H3N O2 . 0.82(4) 1.89(4) 2.716(4) 176(4)
    N3 H4N O3 . 0.87(8) 1.73(8) 2.594(3) 166(6)
    N4 H5N O2 1_455 0.82(4) 2.07(4) 2.804(4) 148(4)
    N4 H6N O4 . 0.92(4) 1.93(4) 2.842(4) 169(3)
    O3 H1O N3 . 0.82(10) 1.78(10) 2.594(3) 174(8)
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.933
_shelx_estimated_absorpt_T_max     0.996
data_global
_journal_date_recd_electronic     2018-12-10
_journal_date_accepted     2018-12-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      2
_journal_page_first     167
_journal_page_last     174
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989018018224
_journal_coeditor_code     MW2140
_publ_contact_author_name     'William T A Harrison'
_publ_contact_author_address
;
Department of Chemistry
University of Aberdeen
Meston Walk
Aberdeen AB24 3UE
Scotland
;
_publ_contact_author_email     w.harrison@abdn.ac.uk
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with
carboxylates: a robust R₂²(8) supramolecular motif (even when
disordered)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mohammed A. E. Shaibah' .
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri
Mysuru 570 006
India
;
    'Belakavadi K. Sagar' .
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri
Mysuru 570 006
India
;
    'Hemmige S. Yathirajan' .
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri
Mysuru 570 006
India
;
    'Cordes, David B.' .
;
School of Chemistry
University of St Andrews
Fife KY16 9ST
Scotland
;
    'Slawin, Alexandra M. Z.' .
;
School of Chemistry
University of St Andrews
Fife KY16 9ST
Scotland
;
    'Harrison, William T. A.' .
;
Department of Chemistry
University of Aberdeen
Meston Walk
Aberdeen AB24 3UE
Scotland
;
_publ_section_synopsis
;
The syntheses and structures of five molecular salts of protonated
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine
(C₁₁H₁₉N₂S⁺) with different deprotonated carboxylic acids
(4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric
acid and succinic acid) are reported.In every case, the cation protonation
occurs at the N atom of the thiazole ring and the six-membered ring adopts a
half-chair conformation (in some cases, the deviating methylene groups are
disordered over two sets of sites). The C---N bond lengths of the nominal
--NH⁺=C---NH₂ fragment of the cation are indistinguishable, indicating
a significant contribution of the --NH---C=N⁺H₂ resonance form to the
structure.
;
