##############################################################################
#                                                                            #
# 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.                                        #
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##############################################################################
data_global
_audit_creation_method     'from SHELXL-2014'
_journal_date_recd_electronic     2020-02-14
_journal_date_accepted     2020-02-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue      4
_journal_page_first     488
_journal_page_last     495
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989020002844
_journal_coeditor_code     ZL2772
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Yathirajan, Hemmige S.'
;
Department of Studies in Chemistry,
University of Mysore,
Manasagangotri, Mysuru 570 006,
India
;
 yathirajan@hotmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structures of the recreational drug N-(4-methoxyphenyl)piperazine
(MeOPP) and three of its salts
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kiran Kumar, Haruvegowda' .
;  Department of Studies in Chemistry,
University of Mysore,
Manasagangotri, Mysuru 570 006,
India
;
    'Yathirajan, Hemmige S.' .
;  Department of Studies in Chemistry,
University of Mysore,
Manasagangotri, Mysuru 570 006,
India
;
    'Harish Chinthal, Chayanna' .
;  Department of Studies in Chemistry,
University of Mysore,
Manasagangotri, Mysuru 570 006,
India
;
    'Foro, Sabine' .
; Institute of Materials Science,
Darmstadt University of Technology,
Alarich-Weiss-Strasse 2,
D-64287 Darmstadt,
Germany
;
    'Glidewell, Christopher' .
;    School of Chemistry, University of St Andrews,
     St Andrews, Fife KY16 9ST, UK
;
_publ_section_synopsis
;
The hydrogen-bonded assemblies in N-(4-methoxyphenyl)piperazine and its
3,5-dinitrobenzoate, picrate, and monohydrated 4-aminobenzoate salts are,
respectively, one-, zero-, two- and three-dimensional.
;
data_I
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;
N-(4-Methoxyphenyl)piperazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H16 N2 O'
_chemical_formula_sum     'C11 H16 N2 O'
_chemical_formula_iupac     'C11 H16 N2 O'
_chemical_formula_weight     192.26
_chemical_melting_point     ?
_chemical_absolute_configuration     unk
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     6.9683(7)
_cell_length_b     7.9683(8)
_cell_length_c     18.975(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1053.60(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1984
_cell_measurement_theta_min     2.772
_cell_measurement_theta_max     27.706
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.480
_exptl_crystal_size_mid     0.480
_exptl_crystal_size_min     0.400
_exptl_crystal_density_diffrn     1.212
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     416
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.814
_exptl_absorpt_correction_T_max     0.969
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4066
_diffrn_reflns_av_R_equivalents     0.0119
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_theta_min     2.772
_diffrn_reflns_theta_max     27.706
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.938
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     1984
_reflns_number_gt     1545
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0508
_refine_ls_R_factor_gt     0.0355
_refine_ls_wR_factor_gt     0.0815
_refine_ls_wR_factor_ref     0.0884
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     1984
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0466P)²+0.0420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.104
_refine_diff_density_min     -0.116
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 546 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
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
    N N1 0.7092(4) 0.4549(3) 0.62326(14) 0.0784(6) Uani d 1 . .
    H H1 0.790(5) 0.480(4) 0.6597(19) 0.094 Uiso d 1 . .
    C C2 0.8074(4) 0.4800(3) 0.55762(17) 0.0709(7) Uani d 1 . .
    H H2A 0.9239 0.4134 0.5568 0.085 Uiso calc 1 . .
    H H2B 0.8428 0.5972 0.5528 0.085 Uiso calc 1 . .
    C C3 0.6799(3) 0.4296(3) 0.49739(15) 0.0617(6) Uani d 1 . .
    H H3A 0.7453 0.4509 0.4532 0.074 Uiso calc 1 . .
    H H3B 0.6531 0.3103 0.5002 0.074 Uiso calc 1 . .
    N N4 0.4997(3) 0.5231(2) 0.49904(11) 0.0502(4) Uani d 1 . .
    C C5 0.4049(3) 0.5099(3) 0.56726(13) 0.0582(6) Uani d 1 . .
    H H5A 0.3622 0.3954 0.5746 0.070 Uiso calc 1 . .
    H H5B 0.2930 0.5823 0.5680 0.070 Uiso calc 1 . .
    C C6 0.5390(4) 0.5596(4) 0.62554(15) 0.0716(7) Uani d 1 . .
    H H6A 0.5749 0.6765 0.6203 0.086 Uiso calc 1 . .
    H H6B 0.4754 0.5464 0.6707 0.086 Uiso calc 1 . .
    C C21 0.3791(3) 0.5080(2) 0.43961(12) 0.0465(5) Uani d 1 . .
    C C22 0.4222(3) 0.4034(3) 0.38284(13) 0.0568(6) Uani d 1 . .
    H H22 0.5303 0.3351 0.3848 0.068 Uiso calc 1 . .
    C C23 0.3067(4) 0.3998(3) 0.32390(13) 0.0614(6) Uani d 1 . .
    H H23 0.3391 0.3300 0.2864 0.074 Uiso calc 1 . .
    C C24 0.1445(4) 0.4975(3) 0.31948(13) 0.0568(7) Uani d 1 . .
    C C25 0.0979(3) 0.6002(3) 0.37552(14) 0.0567(6) Uani d 1 . .
    H H25 -0.0117 0.6665 0.3736 0.068 Uiso calc 1 . .
    C C26 0.2136(3) 0.6042(2) 0.43401(13) 0.0539(6) Uani d 1 . .
    H H26 0.1799 0.6739 0.4713 0.065 Uiso calc 1 . .
    O O24 0.0395(3) 0.4861(2) 0.25830(11) 0.0798(6) Uani d 1 . .
    C C27 -0.1153(4) 0.5990(5) 0.2494(2) 0.1065(12) Uani d 1 . .
    H H27A -0.1652 0.5889 0.2024 0.160 Uiso calc 1 . .
    H H27B -0.0713 0.7118 0.2570 0.160 Uiso calc 1 . .
    H H27C -0.2145 0.5731 0.2828 0.160 Uiso calc 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
    N1 C2 . 1.435(4) ?
    N1 C6 . 1.451(4) ?
    N1 H1 . 0.91(4) ?
    C2 C3 . 1.502(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N4 . 1.460(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    N4 C21 . 1.411(3) ?
    N4 C5 . 1.457(3) ?
    C5 C6 . 1.501(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C21 C26 . 1.389(3) ?
    C21 C22 . 1.395(3) ?
    C22 C23 . 1.378(4) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.375(3) ?
    C23 H23 . 0.9300 ?
    C24 O24 . 1.375(3) ?
    C24 C25 . 1.380(4) ?
    C25 C26 . 1.372(4) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    O24 C27 . 1.415(4) ?
    C27 H27A . 0.9600 ?
    C27 H27B . 0.9600 ?
    C27 H27C . 0.9600 ?
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
    C2 N1 C6 . . 109.6(2) ?
    C2 N1 H1 . . 110(2) ?
    C6 N1 H1 . . 111(2) ?
    N1 C2 C3 . . 109.9(2) ?
    N1 C2 H2A . . 109.7 ?
    C3 C2 H2A . . 109.7 ?
    N1 C2 H2B . . 109.7 ?
    C3 C2 H2B . . 109.7 ?
    H2A C2 H2B . . 108.2 ?
    N4 C3 C2 . . 110.8(2) ?
    N4 C3 H3A . . 109.5 ?
    C2 C3 H3A . . 109.5 ?
    N4 C3 H3B . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.1 ?
    C21 N4 C5 . . 115.72(15) ?
    C21 N4 C3 . . 116.8(2) ?
    C5 N4 C3 . . 111.8(2) ?
    N4 C5 C6 . . 110.71(18) ?
    N4 C5 H5A . . 109.5 ?
    C6 C5 H5A . . 109.5 ?
    N4 C5 H5B . . 109.5 ?
    C6 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 108.1 ?
    N1 C6 C5 . . 109.6(2) ?
    N1 C6 H6A . . 109.7 ?
    C5 C6 H6A . . 109.7 ?
    N1 C6 H6B . . 109.7 ?
    C5 C6 H6B . . 109.7 ?
    H6A C6 H6B . . 108.2 ?
    C26 C21 C22 . . 116.7(2) ?
    C26 C21 N4 . . 120.58(19) ?
    C22 C21 N4 . . 122.66(19) ?
    C23 C22 C21 . . 120.9(2) ?
    C23 C22 H22 . . 119.6 ?
    C21 C22 H22 . . 119.6 ?
    C24 C23 C22 . . 121.2(2) ?
    C24 C23 H23 . . 119.4 ?
    C22 C23 H23 . . 119.4 ?
    O24 C24 C23 . . 116.8(2) ?
    O24 C24 C25 . . 124.4(2) ?
    C23 C24 C25 . . 118.8(2) ?
    C26 C25 C24 . . 119.9(2) ?
    C26 C25 H25 . . 120.0 ?
    C24 C25 H25 . . 120.0 ?
    C25 C26 C21 . . 122.5(2) ?
    C25 C26 H26 . . 118.8 ?
    C21 C26 H26 . . 118.8 ?
    C24 O24 C27 . . 117.7(2) ?
    O24 C27 H27A . . 109.5 ?
    O24 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    O24 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
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 N1 C2 C3 . . . . -61.6(3) ?
    N1 C2 C3 N4 . . . . 57.0(3) ?
    C2 C3 N4 C21 . . . . 170.30(19) ?
    C2 C3 N4 C5 . . . . -53.1(3) ?
    C21 N4 C5 C6 . . . . -169.38(19) ?
    C3 N4 C5 C6 . . . . 53.5(2) ?
    C2 N1 C6 C5 . . . . 61.8(3) ?
    N4 C5 C6 N1 . . . . -57.4(3) ?
    C5 N4 C21 C26 . . . . 50.9(2) ?
    C3 N4 C21 C26 . . . . -174.17(19) ?
    C5 N4 C21 C22 . . . . -131.9(2) ?
    C3 N4 C21 C22 . . . . 3.0(3) ?
    C26 C21 C22 C23 . . . . 1.3(3) ?
    N4 C21 C22 C23 . . . . -176.0(2) ?
    C21 C22 C23 C24 . . . . -0.8(3) ?
    C22 C23 C24 O24 . . . . 179.5(2) ?
    C22 C23 C24 C25 . . . . -0.1(3) ?
    O24 C24 C25 C26 . . . . -179.1(2) ?
    C23 C24 C25 C26 . . . . 0.5(3) ?
    C24 C25 C26 C21 . . . . 0.1(3) ?
    C22 C21 C26 C25 . . . . -1.0(3) ?
    N4 C21 C26 C25 . . . . 176.40(19) ?
    C23 C24 O24 C27 . . . . -173.1(3) ?
    C25 C24 O24 C27 . . . . 6.6(4) ?
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
    _geom_hbond_publ_flag
    N1 H1 O24 2_665 0.91(4) 2.23(4) 3.139(3) 171(3) no
_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     0.963
_shelx_estimated_absorpt_T_max     0.969
_shelxl_version_number        2.014
data_II
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;
4-(4-Methoxyphenyl)piperazin-1-ium 3,5-dinitrobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H17 N2 O +, C7 H3 N2 O6 -'
_chemical_formula_sum     'C18 H20 N4 O7'
_chemical_formula_iupac     'C11 H17 N2 O +, C7 H3 N2 O6 -'
_chemical_formula_weight     404.38
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.4365(4)
_cell_length_b     10.6276(6)
_cell_length_c     13.2700(6)
_cell_angle_alpha     92.238(4)
_cell_angle_beta     97.057(4)
_cell_angle_gamma     108.618(5)
_cell_volume     982.92(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4210
_cell_measurement_theta_min     2.655
_cell_measurement_theta_max     27.755
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.500
_exptl_crystal_size_mid     0.480
_exptl_crystal_size_min     0.480
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     0.107
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.765
_exptl_absorpt_correction_T_max     0.950
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7013
_diffrn_reflns_av_R_equivalents     0.0105
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_theta_min     2.655
_diffrn_reflns_theta_max     27.534
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.928
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     4202
_reflns_number_gt     3057
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0600
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.1000
_refine_ls_wR_factor_ref     0.1097
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     4202
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0482P)²+0.2082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.146
_refine_diff_density_min     -0.187
_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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
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
    N N1 0.4909(2) 0.44996(14) 0.34081(10) 0.0521(3) Uani d 1 . .
    H H11 0.578(3) 0.5249(19) 0.3837(14) 0.063 Uiso d 1 . .
    H H12 0.464(3) 0.3711(18) 0.3776(14) 0.063 Uiso d 1 . .
    C C2 0.3094(3) 0.47725(16) 0.31197(13) 0.0579(4) Uani d 1 . .
    H H2A 0.2620 0.4993 0.3729 0.070 Uiso calc 1 . .
    H H2B 0.2140 0.3982 0.2761 0.070 Uiso calc 1 . .
    C C3 0.3399(3) 0.59140(16) 0.24455(12) 0.0518(4) Uani d 1 . .
    H H3A 0.2191 0.6068 0.2249 0.062 Uiso calc 1 . .
    H H3B 0.4290 0.6719 0.2819 0.062 Uiso calc 1 . .
    N N4 0.41580(19) 0.56126(12) 0.15311(9) 0.0475(3) Uani d 1 . .
    C C5 0.5974(3) 0.54000(17) 0.18174(12) 0.0532(4) Uani d 1 . .
    H H5A 0.6890 0.6204 0.2180 0.064 Uiso calc 1 . .
    H H5B 0.6473 0.5205 0.1209 0.064 Uiso calc 1 . .
    C C6 0.5732(3) 0.42574(17) 0.24871(13) 0.0601(5) Uani d 1 . .
    H H6A 0.4893 0.3441 0.2105 0.072 Uiso calc 1 . .
    H H6B 0.6967 0.4147 0.2689 0.072 Uiso calc 1 . .
    C C21 0.4128(2) 0.65236(14) 0.07691(11) 0.0443(3) Uani d 1 . .
    C C22 0.2377(2) 0.65974(17) 0.03241(12) 0.0555(4) Uani d 1 . .
    H H22 0.1256 0.6063 0.0536 0.067 Uiso calc 1 . .
    C C23 0.2264(2) 0.74413(18) -0.04220(13) 0.0572(4) Uani d 1 . .
    H H23 0.1074 0.7474 -0.0706 0.069 Uiso calc 1 . .
    C C24 0.3915(2) 0.82446(16) -0.07540(11) 0.0468(4) Uani d 1 . .
    C C25 0.5662(2) 0.81844(16) -0.03278(11) 0.0477(4) Uani d 1 . .
    H H25 0.6779 0.8715 -0.0546 0.057 Uiso calc 1 . .
    C C26 0.5764(2) 0.73326(16) 0.04294(11) 0.0477(4) Uani d 1 . .
    H H26 0.6957 0.7305 0.0714 0.057 Uiso calc 1 . .
    O O24 0.36537(16) 0.90394(12) -0.15109(9) 0.0609(3) Uani d 1 . .
    C C27 0.5312(2) 0.98606(18) -0.18771(14) 0.0595(4) Uani d 1 . .
    H H27A 0.4941 1.0364 -0.2401 0.089 Uiso calc 1 . .
    H H27B 0.6143 1.0459 -0.1327 0.089 Uiso calc 1 . .
    H H27C 0.5973 0.9314 -0.2151 0.089 Uiso calc 1 . .
    C C31 0.75477(19) 0.90885(13) 0.44906(10) 0.0370(3) Uani d 1 . .
    C C32 0.74671(19) 1.02627(13) 0.49332(11) 0.0379(3) Uani d 1 . .
    H H32 0.6919 1.0266 0.5526 0.045 Uiso calc 1 . .
    C C33 0.8211(2) 1.14339(13) 0.44845(11) 0.0397(3) Uani d 1 . .
    C C34 0.9027(2) 1.14837(15) 0.36080(11) 0.0425(3) Uani d 1 . .
    H H34 0.9502 1.2278 0.3310 0.051 Uiso calc 1 . .
    C C35 0.91080(19) 1.03023(15) 0.31926(10) 0.0416(3) Uani d 1 . .
    C C36 0.8395(2) 0.91119(14) 0.36128(11) 0.0413(3) Uani d 1 . .
    H H36 0.8480 0.8331 0.3312 0.050 Uiso calc 1 . .
    C C37 0.6792(2) 0.77976(14) 0.49869(12) 0.0442(3) Uani d 1 . .
    O O31 0.70674(18) 0.67975(10) 0.46073(10) 0.0624(3) Uani d 1 . .
    O O32 0.59993(18) 0.78544(11) 0.57568(10) 0.0617(3) Uani d 1 . .
    N N33 0.8205(2) 1.26892(13) 0.49865(12) 0.0556(4) Uani d 1 . .
    O O33 0.7947(3) 1.26858(14) 0.58726(12) 0.0877(5) Uani d 1 . .
    O O34 0.8460(2) 1.36548(11) 0.44914(12) 0.0745(4) Uani d 1 . .
    N N35 1.00278(19) 1.03268(17) 0.22712(11) 0.0575(4) Uani d 1 . .
    O O35 0.9969(2) 0.92646(16) 0.18661(11) 0.0886(5) Uani d 1 . .
    O O36 1.08186(19) 1.14064(15) 0.19653(10) 0.0723(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
    N1 C2 . 1.478(2) ?
    N1 C6 . 1.481(2) ?
    N1 H11 . 0.96(2) ?
    N1 H12 . 0.965(18) ?
    C2 C3 . 1.511(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N4 . 1.4654(19) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    N4 C21 . 1.4301(18) ?
    N4 C5 . 1.448(2) ?
    C5 C6 . 1.510(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C21 C26 . 1.386(2) ?
    C21 C22 . 1.389(2) ?
    C22 C23 . 1.374(2) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.387(2) ?
    C23 H23 . 0.9300 ?
    C24 O24 . 1.3724(18) ?
    C24 C25 . 1.373(2) ?
    C25 C26 . 1.390(2) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    O24 C27 . 1.4181(19) ?
    C27 H27A . 0.9600 ?
    C27 H27B . 0.9600 ?
    C27 H27C . 0.9600 ?
    C31 C32 . 1.3803(19) ?
    C31 C36 . 1.388(2) ?
    C31 C37 . 1.5169(19) ?
    C32 C33 . 1.3817(19) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.372(2) ?
    C33 N33 . 1.4693(19) ?
    C34 C35 . 1.374(2) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.376(2) ?
    C35 N35 . 1.4696(19) ?
    C36 H36 . 0.9300 ?
    C37 O31 . 1.2440(18) ?
    C37 O32 . 1.2495(19) ?
    N33 O33 . 1.2143(19) ?
    N33 O34 . 1.2165(17) ?
    N35 O35 . 1.2169(19) ?
    N35 O36 . 1.2211(18) ?
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
    C2 N1 C6 . . 110.43(13) ?
    C2 N1 H11 . . 108.2(11) ?
    C6 N1 H11 . . 111.1(11) ?
    C2 N1 H12 . . 108.4(11) ?
    C6 N1 H12 . . 108.7(10) ?
    H11 N1 H12 . . 110.0(15) ?
    N1 C2 C3 . . 110.47(14) ?
    N1 C2 H2A . . 109.6 ?
    C3 C2 H2A . . 109.6 ?
    N1 C2 H2B . . 109.6 ?
    C3 C2 H2B . . 109.6 ?
    H2A C2 H2B . . 108.1 ?
    N4 C3 C2 . . 110.40(13) ?
    N4 C3 H3A . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    N4 C3 H3B . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.1 ?
    C21 N4 C5 . . 115.97(12) ?
    C21 N4 C3 . . 113.26(12) ?
    C5 N4 C3 . . 109.90(12) ?
    N4 C5 C6 . . 110.50(14) ?
    N4 C5 H5A . . 109.6 ?
    C6 C5 H5A . . 109.6 ?
    N4 C5 H5B . . 109.6 ?
    C6 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.1 ?
    N1 C6 C5 . . 111.08(13) ?
    N1 C6 H6A . . 109.4 ?
    C5 C6 H6A . . 109.4 ?
    N1 C6 H6B . . 109.4 ?
    C5 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    C26 C21 C22 . . 117.42(14) ?
    C26 C21 N4 . . 123.45(14) ?
    C22 C21 N4 . . 119.12(14) ?
    C23 C22 C21 . . 121.53(15) ?
    C23 C22 H22 . . 119.2 ?
    C21 C22 H22 . . 119.2 ?
    C22 C23 C24 . . 120.35(15) ?
    C22 C23 H23 . . 119.8 ?
    C24 C23 H23 . . 119.8 ?
    O24 C24 C25 . . 124.83(14) ?
    O24 C24 C23 . . 116.04(14) ?
    C25 C24 C23 . . 119.13(14) ?
    C24 C25 C26 . . 120.16(14) ?
    C24 C25 H25 . . 119.9 ?
    C26 C25 H25 . . 119.9 ?
    C21 C26 C25 . . 121.40(15) ?
    C21 C26 H26 . . 119.3 ?
    C25 C26 H26 . . 119.3 ?
    C24 O24 C27 . . 117.47(13) ?
    O24 C27 H27A . . 109.5 ?
    O24 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    O24 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C32 C31 C36 . . 119.36(12) ?
    C32 C31 C37 . . 120.07(13) ?
    C36 C31 C37 . . 120.52(13) ?
    C31 C32 C33 . . 119.18(13) ?
    C31 C32 H32 . . 120.4 ?
    C33 C32 H32 . . 120.4 ?
    C34 C33 C32 . . 122.74(13) ?
    C34 C33 N33 . . 118.33(13) ?
    C32 C33 N33 . . 118.88(13) ?
    C33 C34 C35 . . 116.73(13) ?
    C33 C34 H34 . . 121.6 ?
    C35 C34 H34 . . 121.6 ?
    C34 C35 C36 . . 122.71(13) ?
    C34 C35 N35 . . 118.15(13) ?
    C36 C35 N35 . . 119.13(14) ?
    C35 C36 C31 . . 119.26(13) ?
    C35 C36 H36 . . 120.4 ?
    C31 C36 H36 . . 120.4 ?
    O31 C37 O32 . . 126.39(14) ?
    O31 C37 C31 . . 117.10(14) ?
    O32 C37 C31 . . 116.49(13) ?
    O33 N33 O34 . . 124.64(15) ?
    O33 N33 C33 . . 117.22(13) ?
    O34 N33 C33 . . 118.14(15) ?
    O35 N35 O36 . . 124.03(15) ?
    O35 N35 C35 . . 117.67(15) ?
    O36 N35 C35 . . 118.29(15) ?
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 N1 C2 C3 . . . . -55.07(17) ?
    N1 C2 C3 N4 . . . . 57.89(18) ?
    C2 C3 N4 C21 . . . . 168.46(14) ?
    C2 C3 N4 C5 . . . . -60.05(18) ?
    C21 N4 C5 C6 . . . . -170.46(12) ?
    C3 N4 C5 C6 . . . . 59.49(16) ?
    C2 N1 C6 C5 . . . . 54.81(19) ?
    N4 C5 C6 N1 . . . . -57.29(19) ?
    C5 N4 C21 C26 . . . . -10.3(2) ?
    C3 N4 C21 C26 . . . . 118.13(17) ?
    C5 N4 C21 C22 . . . . 168.48(14) ?
    C3 N4 C21 C22 . . . . -63.10(18) ?
    C26 C21 C22 C23 . . . . -0.2(2) ?
    N4 C21 C22 C23 . . . . -179.05(15) ?
    C21 C22 C23 C24 . . . . 0.2(3) ?
    C22 C23 C24 O24 . . . . 179.14(16) ?
    C22 C23 C24 C25 . . . . 0.0(3) ?
    O24 C24 C25 C26 . . . . -179.33(14) ?
    C23 C24 C25 C26 . . . . -0.3(2) ?
    C22 C21 C26 C25 . . . . -0.1(2) ?
    N4 C21 C26 C25 . . . . 178.71(14) ?
    C24 C25 C26 C21 . . . . 0.3(2) ?
    C25 C24 O24 C27 . . . . -0.2(2) ?
    C23 C24 O24 C27 . . . . -179.20(15) ?
    C36 C31 C32 C33 . . . . 0.8(2) ?
    C37 C31 C32 C33 . . . . 178.20(12) ?
    C31 C32 C33 C34 . . . . 0.3(2) ?
    C31 C32 C33 N33 . . . . -177.08(13) ?
    C32 C33 C34 C35 . . . . -1.1(2) ?
    N33 C33 C34 C35 . . . . 176.30(13) ?
    C33 C34 C35 C36 . . . . 0.8(2) ?
    C33 C34 C35 N35 . . . . -178.10(13) ?
    C34 C35 C36 C31 . . . . 0.3(2) ?
    N35 C35 C36 C31 . . . . 179.18(12) ?
    C32 C31 C36 C35 . . . . -1.1(2) ?
    C37 C31 C36 C35 . . . . -178.48(12) ?
    C32 C31 C37 O31 . . . . -173.38(14) ?
    C36 C31 C37 O31 . . . . 4.0(2) ?
    C32 C31 C37 O32 . . . . 4.7(2) ?
    C36 C31 C37 O32 . . . . -177.93(13) ?
    C34 C33 N33 O33 . . . . -161.49(16) ?
    C32 C33 N33 O33 . . . . 16.0(2) ?
    C34 C33 N33 O34 . . . . 18.4(2) ?
    C32 C33 N33 O34 . . . . -164.13(14) ?
    C34 C35 N35 O35 . . . . -174.75(15) ?
    C36 C35 N35 O35 . . . . 6.3(2) ?
    C34 C35 N35 O36 . . . . 6.0(2) ?
    C36 C35 N35 O36 . . . . -172.92(14) ?
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
    _geom_hbond_publ_flag
    N1 H11 O31 . 0.96(2) 1.814(19) 2.7638(18) 169(2) no
    N1 H12 O32 2_666 0.964(18) 1.740(18) 2.6953(18) 170.5(17) no
_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     0.948
_shelx_estimated_absorpt_T_max     0.950
_shelxl_version_number        2.014
data_III
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;
4-(4-Methoxyphenyl)piperazin-1-ium 2,4,6-trinitrophenolate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H17 N2 O +, C6 H2 N3 O7 -'
_chemical_formula_sum     'C17 H19 N5 O8'
_chemical_formula_iupac     'C11 H17 N2 O +, C6 H2 N3 O7 -'
_chemical_formula_weight     421.37
_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     8.7568(6)
_cell_length_b     6.6292(5)
_cell_length_c     34.024(2)
_cell_angle_alpha     90
_cell_angle_beta     96.987(6)
_cell_angle_gamma     90
_cell_volume     1960.4(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4353
_cell_measurement_theta_min     2.781
_cell_measurement_theta_max     27.943
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.480
_exptl_crystal_size_mid     0.420
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.428
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     880
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.844
_exptl_absorpt_correction_T_max     0.977
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14483
_diffrn_reflns_av_R_equivalents     0.0230
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_theta_min     2.781
_diffrn_reflns_theta_max     27.943
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.923
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -40
_diffrn_reflns_limit_l_max     42
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     4353
_reflns_number_gt     2844
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0970
_refine_ls_R_factor_gt     0.0575
_refine_ls_wR_factor_gt     0.1196
_refine_ls_wR_factor_ref     0.1360
_refine_ls_goodness_of_fit_ref     1.093
_refine_ls_restrained_S_all     1.072
_refine_ls_number_reflns     4353
_refine_ls_number_parameters     333
_refine_ls_number_restraints     216
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0408P)²+1.0520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.176
_refine_diff_density_min     -0.179
_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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
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
    N N1 0.0738(2) 0.1834(3) 0.59884(5) 0.0479(5) Uani d 1 . .
    H H11 0.151(3) 0.169(4) 0.5830(7) 0.058 Uiso d 1 . .
    H H12 -0.019(3) 0.169(4) 0.5837(7) 0.058 Uiso d 1 . .
    C C2 0.0862(3) 0.0294(4) 0.63061(6) 0.0525(6) Uani d 1 . .
    H H2A 0.0870 -0.1042 0.6190 0.063 Uiso calc 1 . .
    H H2B -0.0021 0.0387 0.6452 0.063 Uiso calc 1 . .
    C C3 0.2321(3) 0.0615(4) 0.65845(7) 0.0500(6) Uani d 1 . .
    H H3A 0.2374 -0.0366 0.6797 0.060 Uiso calc 1 . .
    H H3B 0.3205 0.0412 0.6443 0.060 Uiso calc 1 . .
    N N4 0.23682(19) 0.2647(3) 0.67506(5) 0.0400(4) Uani d 1 . .
    C C5 0.2311(3) 0.4129(4) 0.64346(6) 0.0466(6) Uani d 1 . .
    H H5A 0.3190 0.3950 0.6290 0.056 Uiso calc 1 . .
    H H5B 0.2362 0.5476 0.6547 0.056 Uiso calc 1 . .
    C C6 0.0844(3) 0.3897(4) 0.61558(7) 0.0541(6) Uani d 1 . .
    H H6A -0.0033 0.4153 0.6297 0.065 Uiso calc 1 . .
    H H6B 0.0827 0.4874 0.5943 0.065 Uiso calc 1 . .
    C C21 0.3552(2) 0.2940(3) 0.70738(6) 0.0395(5) Uani d 1 . .
    C C22 0.3572(3) 0.1707(4) 0.74060(6) 0.0484(6) Uani d 1 . .
    H H22 0.2840 0.0692 0.7409 0.058 Uiso calc 1 . .
    C C23 0.4660(3) 0.1966(4) 0.77304(6) 0.0544(7) Uani d 1 . .
    H H23 0.4667 0.1108 0.7947 0.065 Uiso calc 1 . .
    C C24 0.5738(3) 0.3482(4) 0.77367(6) 0.0528(6) Uani d 1 . .
    C C25 0.5737(3) 0.4715(4) 0.74137(7) 0.0562(7) Uani d 1 . .
    H H25 0.6457 0.5747 0.7415 0.067 Uiso calc 1 . .
    C C26 0.4657(3) 0.4422(4) 0.70826(6) 0.0487(6) Uani d 1 . .
    H H26 0.4684 0.5247 0.6862 0.058 Uiso calc 1 . .
    O O24 0.6749(2) 0.3618(3) 0.80799(5) 0.0735(6) Uani d 1 . .
    C C27 0.7871(4) 0.5171(6) 0.81017(8) 0.1008(13) Uani d 1 . .
    H H27A 0.8500 0.5107 0.8353 0.151 Uiso calc 1 . .
    H H27B 0.8505 0.4998 0.7893 0.151 Uiso calc 1 . .
    H H27C 0.7368 0.6458 0.8074 0.151 Uiso calc 1 . .
    C C31 0.3734(2) 0.2329(3) 0.52703(6) 0.0356(5) Uani d 1 . .
    O O31 0.32183(18) 0.2105(3) 0.55895(4) 0.0597(5) Uani d 1 . .
    C C33 0.5987(2) 0.2562(3) 0.48889(6) 0.0370(5) Uani d 1 . .
    H H33 0.7047 0.2625 0.4888 0.044 Uiso calc 1 A 1
    C C34 0.5007(2) 0.2576(3) 0.45381(6) 0.0383(5) Uani d 1 . .
    C C35 0.3436(2) 0.2518(3) 0.45352(6) 0.0393(5) Uani d 1 . .
    H H35 0.2796 0.2548 0.4296 0.047 Uiso calc 1 B 3
    C C32 0.5365(2) 0.2455(3) 0.52377(6) 0.0339(4) Uani d 0.531(16) C 1
    N N32 0.6471(5) 0.244(2) 0.55966(13) 0.036(3) Uani d 0.531(16) C 1
    O O32 0.6107(6) 0.1681(18) 0.58975(13) 0.068(2) Uani d 0.531(16) C 1
    O O33 0.7762(6) 0.3080(16) 0.55749(18) 0.0608(18) Uani d 0.531(16) C 1
    C C42 0.5365(2) 0.2455(3) 0.52377(6) 0.0339(4) Uani d 0.469(16) C 2
    N N42 0.6434(7) 0.242(3) 0.55983(17) 0.056(5) Uani d 0.469(16) C 2
    O O42 0.6039(6) 0.306(2) 0.59065(15) 0.071(3) Uani d 0.469(16) C 2
    O O43 0.7755(7) 0.191(2) 0.5573(2) 0.073(2) Uani d 0.469(16) C 2
    N N34 0.5657(2) 0.2627(3) 0.41672(5) 0.0514(5) Uani d 1 . .
    O O34 0.7052(2) 0.2600(3) 0.41785(5) 0.0689(5) Uani d 1 . .
    O O35 0.4782(2) 0.2684(3) 0.38591(5) 0.0800(6) Uani d 1 . .
    C C36 0.2819(2) 0.2416(3) 0.48841(6) 0.0370(5) Uani d 0.62(6) C 3
    N N36 0.1151(5) 0.2315(18) 0.4864(3) 0.056(3) Uani d 0.62(6) C 3
    O O36 0.0431(11) 0.178(4) 0.4554(4) 0.096(4) Uani d 0.62(6) C 3
    O O37 0.0549(12) 0.301(3) 0.5138(3) 0.084(3) Uani d 0.62(6) C 3
    C C46 0.2819(2) 0.2416(3) 0.48841(6) 0.0370(5) Uani d 0.38(6) C 4
    N N46 0.1144(7) 0.238(3) 0.4844(3) 0.055(5) Uani d 0.38(6) C 4
    O O46 0.0441(16) 0.215(5) 0.4518(4) 0.080(5) Uani d 0.38(6) C 4
    O O47 0.0510(15) 0.227(9) 0.5144(4) 0.089(7) Uani d 0.38(6) C 4
_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
    N1 C6 . 1.480(3) ?
    N1 C2 . 1.481(3) ?
    N1 H11 . 0.92(3) ?
    N1 H12 . 0.91(3) ?
    C2 C3 . 1.510(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N4 . 1.460(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    N4 C21 . 1.430(3) ?
    N4 C5 . 1.453(3) ?
    C5 C6 . 1.509(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C21 C26 . 1.377(3) ?
    C21 C22 . 1.393(3) ?
    C22 C23 . 1.378(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.377(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.369(3) ?
    C24 O24 . 1.380(3) ?
    C25 C26 . 1.393(3) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    O24 C27 . 1.419(4) ?
    C27 H27A . 0.9600 ?
    C27 H27B . 0.9600 ?
    C27 H27C . 0.9600 ?
    C31 O31 . 1.235(2) ?
    C31 C32 . 1.448(3) ?
    C31 C36 . 1.455(3) ?
    C33 C32 . 1.366(3) ?
    C33 C34 . 1.383(3) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.375(3) ?
    C34 N34 . 1.446(3) ?
    C35 C36 . 1.364(3) ?
    C35 H35 . 0.9300 ?
    C32 N32 . 1.463(4) ?
    N32 O32 . 1.218(7) ?
    N32 O33 . 1.218(7) ?
    N42 O43 . 1.218(7) ?
    N42 O42 . 1.222(8) ?
    N34 O34 . 1.217(2) ?
    N34 O35 . 1.221(2) ?
    C36 N36 . 1.455(5) ?
    N36 O36 . 1.213(5) ?
    N36 O37 . 1.218(7) ?
    N46 O46 . 1.213(7) ?
    N46 O47 . 1.220(8) ?
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 N1 C2 . . 111.14(18) ?
    C6 N1 H11 . . 107.7(16) ?
    C2 N1 H11 . . 111.3(15) ?
    C6 N1 H12 . . 108.7(16) ?
    C2 N1 H12 . . 108.8(16) ?
    H11 N1 H12 . . 109(2) ?
    N1 C2 C3 . . 110.02(19) ?
    N1 C2 H2A . . 109.7 ?
    C3 C2 H2A . . 109.7 ?
    N1 C2 H2B . . 109.7 ?
    C3 C2 H2B . . 109.7 ?
    H2A C2 H2B . . 108.2 ?
    N4 C3 C2 . . 110.8(2) ?
    N4 C3 H3A . . 109.5 ?
    C2 C3 H3A . . 109.5 ?
    N4 C3 H3B . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.1 ?
    C21 N4 C5 . . 115.72(17) ?
    C21 N4 C3 . . 114.01(17) ?
    C5 N4 C3 . . 109.92(17) ?
    N4 C5 C6 . . 110.26(19) ?
    N4 C5 H5A . . 109.6 ?
    C6 C5 H5A . . 109.6 ?
    N4 C5 H5B . . 109.6 ?
    C6 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.1 ?
    N1 C6 C5 . . 110.2(2) ?
    N1 C6 H6A . . 109.6 ?
    C5 C6 H6A . . 109.6 ?
    N1 C6 H6B . . 109.6 ?
    C5 C6 H6B . . 109.6 ?
    H6A C6 H6B . . 108.1 ?
    C26 C21 C22 . . 117.5(2) ?
    C26 C21 N4 . . 123.74(19) ?
    C22 C21 N4 . . 118.75(19) ?
    C23 C22 C21 . . 121.1(2) ?
    C23 C22 H22 . . 119.5 ?
    C21 C22 H22 . . 119.5 ?
    C24 C23 C22 . . 120.6(2) ?
    C24 C23 H23 . . 119.7 ?
    C22 C23 H23 . . 119.7 ?
    C25 C24 C23 . . 119.3(2) ?
    C25 C24 O24 . . 125.3(2) ?
    C23 C24 O24 . . 115.4(2) ?
    C24 C25 C26 . . 120.0(2) ?
    C24 C25 H25 . . 120.0 ?
    C26 C25 H25 . . 120.0 ?
    C21 C26 C25 . . 121.5(2) ?
    C21 C26 H26 . . 119.2 ?
    C25 C26 H26 . . 119.2 ?
    C24 O24 C27 . . 117.4(2) ?
    O24 C27 H27A . . 109.5 ?
    O24 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    O24 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    O31 C31 C32 . . 122.96(18) ?
    O31 C31 C36 . . 125.38(18) ?
    C32 C33 C34 . . 118.62(18) ?
    C32 C33 H33 . . 120.7 ?
    C34 C33 H33 . . 120.7 ?
    C35 C34 C33 . . 121.41(18) ?
    C35 C34 N34 . . 119.60(18) ?
    C33 C34 N34 . . 118.99(19) ?
    C36 C35 C34 . . 119.79(18) ?
    C36 C35 H35 . . 120.1 ?
    C34 C35 H35 . . 120.1 ?
    C33 C32 C31 . . 124.80(17) ?
    C33 C32 N32 . . 115.6(3) ?
    C31 C32 N32 . . 119.6(3) ?
    O32 N32 O33 . . 122.3(4) ?
    O32 N32 C32 . . 119.3(6) ?
    O33 N32 C32 . . 118.2(5) ?
    O43 N42 O42 . . 122.0(6) ?
    O34 N34 O35 . . 123.3(2) ?
    O34 N34 C34 . . 118.16(19) ?
    O35 N34 C34 . . 118.5(2) ?
    C35 C36 C31 . . 123.71(18) ?
    C35 C36 N36 . . 117.5(4) ?
    C31 C36 N36 . . 118.7(4) ?
    O36 N36 O37 . . 123.3(7) ?
    O36 N36 C36 . . 117.9(6) ?
    O37 N36 C36 . . 118.1(6) ?
    O46 N46 O47 . . 121.8(10) ?
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 N1 C2 C3 . . . . -54.9(3) ?
    N1 C2 C3 N4 . . . . 56.9(2) ?
    C2 C3 N4 C21 . . . . 168.24(18) ?
    C2 C3 N4 C5 . . . . -59.9(2) ?
    C21 N4 C5 C6 . . . . -168.80(19) ?
    C3 N4 C5 C6 . . . . 60.3(2) ?
    C2 N1 C6 C5 . . . . 55.6(2) ?
    N4 C5 C6 N1 . . . . -58.2(2) ?
    C5 N4 C21 C26 . . . . -4.7(3) ?
    C3 N4 C21 C26 . . . . 124.3(2) ?
    C5 N4 C21 C22 . . . . 173.2(2) ?
    C3 N4 C21 C22 . . . . -57.8(3) ?
    C26 C21 C22 C23 . . . . 0.0(3) ?
    N4 C21 C22 C23 . . . . -178.0(2) ?
    C21 C22 C23 C24 . . . . 1.3(4) ?
    C22 C23 C24 C25 . . . . -1.2(4) ?
    C22 C23 C24 O24 . . . . 178.8(2) ?
    C23 C24 C25 C26 . . . . -0.3(4) ?
    O24 C24 C25 C26 . . . . 179.8(2) ?
    C22 C21 C26 C25 . . . . -1.4(3) ?
    N4 C21 C26 C25 . . . . 176.5(2) ?
    C24 C25 C26 C21 . . . . 1.6(4) ?
    C25 C24 O24 C27 . . . . 0.6(4) ?
    C23 C24 O24 C27 . . . . -179.4(3) ?
    C32 C33 C34 C35 . . . . 1.1(3) ?
    C32 C33 C34 N34 . . . . -178.13(19) ?
    C33 C34 C35 C36 . . . . -0.9(3) ?
    N34 C34 C35 C36 . . . . 178.29(19) ?
    C34 C33 C32 C31 . . . . 0.7(3) ?
    C34 C33 C32 N32 . . . . 179.8(6) ?
    O31 C31 C32 C33 . . . . 175.2(2) ?
    C36 C31 C32 C33 . . . . -2.4(3) ?
    O31 C31 C32 N32 . . . . -3.8(7) ?
    C36 C31 C32 N32 . . . . 178.5(6) ?
    C33 C32 N32 O32 . . . . -155.0(10) ?
    C31 C32 N32 O32 . . . . 24.2(15) ?
    C33 C32 N32 O33 . . . . 20.3(13) ?
    C31 C32 N32 O33 . . . . -160.6(8) ?
    C35 C34 N34 O34 . . . . -177.3(2) ?
    C33 C34 N34 O34 . . . . 2.0(3) ?
    C35 C34 N34 O35 . . . . 2.4(3) ?
    C33 C34 N34 O35 . . . . -178.4(2) ?
    C34 C35 C36 C31 . . . . -1.1(3) ?
    C34 C35 C36 N36 . . . . -178.7(6) ?
    O31 C31 C36 C35 . . . . -175.0(2) ?
    C32 C31 C36 C35 . . . . 2.6(3) ?
    O31 C31 C36 N36 . . . . 2.6(6) ?
    C32 C31 C36 N36 . . . . -179.8(6) ?
    C35 C36 N36 O36 . . . . 19.8(18) ?
    C31 C36 N36 O36 . . . . -158.0(16) ?
    C35 C36 N36 O37 . . . . -151.0(14) ?
    C31 C36 N36 O37 . . . . 31.3(17) ?
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
    _geom_hbond_publ_flag
    N1 H11 O31 . 0.92(3) 1.81(3) 2.704(3) 163(2) no
    N1 H11 O37 . 0.92(3) 2.56(3) 2.982(11) 108.7(19) no
    N1 H11 O47 . 0.92(3) 2.42(3) 2.870(15) 110.1(19) no
    N1 H12 O33 1_455 0.91(3) 2.12(3) 2.926(6) 148(2) no
    N1 H12 O43 1_455 0.91(3) 1.92(3) 2.815(6) 168(2) no
    C22 H22 Cg1 2_546 0.93 2.86 3.769(3) 164 no
_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     0.977
_shelxl_version_number        2.014
data_IV
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;
4-(4-Methoxyphenyl)piperazin-1-ium 4-aminobenzoate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H6 N O2 +, C11 H17 N2 O -, H2 O'
_chemical_formula_sum     'C18 H25 N3 O4'
_chemical_formula_iupac     'C7 H6 N O2 +, C11 H17 N2 O -, H2 O'
_chemical_formula_weight     347.41
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.2590(7)
_cell_length_b     7.4549(9)
_cell_length_c     19.269(2)
_cell_angle_alpha     83.280(10)
_cell_angle_beta     84.7400(10)
_cell_angle_gamma     85.380(10)
_cell_volume     886.94(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3815
_cell_measurement_theta_min     2.846
_cell_measurement_theta_max     27.981
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.140
_exptl_crystal_density_diffrn     1.301
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     372
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.814
_exptl_absorpt_correction_T_max     0.987
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5786
_diffrn_reflns_av_R_equivalents     0.0308
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_theta_min     3.066
_diffrn_reflns_theta_max     26.044
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     3500
_reflns_number_gt     1923
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1315
_refine_ls_R_factor_gt     0.0688
_refine_ls_wR_factor_gt     0.1600
_refine_ls_wR_factor_ref     0.1868
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     3500
_refine_ls_number_parameters     240
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0852P)²+0.1253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.235
_refine_diff_density_min     -0.202
_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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
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
    N N1 0.2828(4) 0.7421(3) 0.95242(13) 0.0450(7) Uani d 1 . .
    H H11 0.2404(10) 0.622(3) 0.9597(2) 0.054 Uiso calc 1 . .
    H H12 0.3170(8) 0.7746(7) 0.9957(10) 0.054 Uiso calc 1 . .
    C C2 0.4741(5) 0.7531(5) 0.90102(16) 0.0497(8) Uani d 1 . .
    H H2A 0.5897 0.6695 0.9179 0.060 Uiso calc 1 . .
    H H2B 0.5230 0.8745 0.8959 0.060 Uiso calc 1 . .
    C C3 0.4195(5) 0.7068(4) 0.83065(15) 0.0441(8) Uani d 1 . .
    H H3A 0.5434 0.7229 0.7970 0.053 Uiso calc 1 . .
    H H3B 0.3885 0.5804 0.8349 0.053 Uiso calc 1 . .
    N N4 0.2361(4) 0.8177(3) 0.80430(12) 0.0364(6) Uani d 1 . .
    C C5 0.0500(5) 0.8148(4) 0.85669(15) 0.0439(7) Uani d 1 . .
    H H5A -0.0018 0.6943 0.8637 0.053 Uiso calc 1 . .
    H H5B -0.0648 0.8982 0.8391 0.053 Uiso calc 1 . .
    C C6 0.1042(5) 0.8661(4) 0.92564(15) 0.0483(8) Uani d 1 . .
    H H6A 0.1461 0.9898 0.9197 0.058 Uiso calc 1 . .
    H H6B -0.0212 0.8590 0.9591 0.058 Uiso calc 1 . .
    C C21 0.1873(4) 0.7910(4) 0.73590(14) 0.0360(7) Uani d 1 . .
    C C22 0.3250(5) 0.6885(4) 0.69232(16) 0.0486(8) Uani d 1 . .
    H H22 0.4527 0.6338 0.7084 0.058 Uiso calc 1 . .
    C C23 0.2747(5) 0.6671(5) 0.62568(17) 0.0560(9) Uani d 1 . .
    H H23 0.3696 0.5990 0.5974 0.067 Uiso calc 1 . .
    C C24 0.0876(5) 0.7445(5) 0.60071(16) 0.0492(8) Uani d 1 . .
    C C25 -0.0491(5) 0.8463(5) 0.64207(17) 0.0560(9) Uani d 1 . .
    H H25 -0.1761 0.9008 0.6254 0.067 Uiso calc 1 . .
    C C26 0.0006(5) 0.8689(4) 0.70887(16) 0.0524(9) Uani d 1 . .
    H H26 -0.0947 0.9387 0.7364 0.063 Uiso calc 1 . .
    O O24 0.0508(4) 0.7097(4) 0.53404(12) 0.0751(8) Uani d 1 . .
    C C27 -0.1543(7) 0.7604(7) 0.5111(2) 0.0904(15) Uani d 1 . .
    H H27A -0.2619 0.7136 0.5457 0.136 Uiso calc 1 . .
    H H27B -0.1664 0.7123 0.4676 0.136 Uiso calc 1 . .
    H H27C -0.1748 0.8901 0.5042 0.136 Uiso calc 1 . .
    C C31 0.2985(4) 0.7266(4) 1.20437(15) 0.0377(7) Uani d 1 . .
    C C32 0.1577(5) 0.6559(4) 1.25859(17) 0.0499(8) Uani d 1 . .
    H H32 0.0366 0.6033 1.2480 0.060 Uiso calc 1 . .
    C C33 0.1932(5) 0.6617(4) 1.32757(17) 0.0543(9) Uani d 1 . .
    H H33 0.0961 0.6128 1.3628 0.065 Uiso calc 1 . .
    C C34 0.3719(5) 0.7394(4) 1.34546(16) 0.0501(8) Uani d 1 . .
    C C35 0.5129(5) 0.8063(4) 1.29165(17) 0.0497(8) Uani d 1 . .
    H H35 0.6352 0.8570 1.3023 0.060 Uiso calc 1 . .
    C C36 0.4789(5) 0.8008(4) 1.22268(16) 0.0439(8) Uani d 1 . .
    H H36 0.5781 0.8474 1.1877 0.053 Uiso calc 1 . .
    C C37 0.2566(5) 0.7256(4) 1.12955(17) 0.0477(8) Uani d 1 . .
    O O31 0.3847(4) 0.7999(3) 1.08228(12) 0.0614(7) Uani d 1 . .
    O O32 0.0963(4) 0.6528(4) 1.11651(14) 0.0866(9) Uani d 1 . .
    N N34 0.4074(6) 0.7461(6) 1.41482(17) 0.0767(11) Uani d 1 . .
    H H341 0.312(7) 0.732(6) 1.447(2) 0.092 Uiso d 1 . .
    H H342 0.511(7) 0.811(6) 1.421(2) 0.092 Uiso d 1 . .
    O O41 0.2239(4) 0.3712(3) 0.96061(13) 0.0592(7) Uani d 1 . .
    H H41 0.122(5) 0.361(5) 0.9356(18) 0.089 Uiso d 1 . .
    H H42 0.329(5) 0.307(5) 0.943(2) 0.089 Uiso 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
    N1 C6 . 1.483(4) ?
    N1 C2 . 1.484(4) ?
    N1 H11 . 0.94(2) ?
    N1 H12 . 0.94(2) ?
    C2 C3 . 1.513(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N4 . 1.454(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    N4 C21 . 1.420(3) ?
    N4 C5 . 1.470(3) ?
    C5 C6 . 1.500(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C21 C26 . 1.381(4) ?
    C21 C22 . 1.393(4) ?
    C22 C23 . 1.380(4) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.366(4) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.362(4) ?
    C24 O24 . 1.383(4) ?
    C25 C26 . 1.384(4) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    O24 C27 . 1.405(4) ?
    C27 H27A . 0.9600 ?
    C27 H27B . 0.9600 ?
    C27 H27C . 0.9600 ?
    C31 C32 . 1.387(4) ?
    C31 C36 . 1.387(4) ?
    C31 C37 . 1.490(4) ?
    C32 C33 . 1.374(4) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.388(5) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.373(4) ?
    C34 N34 . 1.382(4) ?
    C35 C36 . 1.371(4) ?
    C35 H35 . 0.9300 ?
    C36 H36 . 0.9300 ?
    C37 O32 . 1.237(4) ?
    C37 O31 . 1.265(4) ?
    N34 H341 . 0.82(4) ?
    N34 H342 . 0.87(4) ?
    O41 H41 . 0.850(19) ?
    O41 H42 . 0.856(19) ?
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 N1 C2 . . 109.6(2) ?
    C6 N1 H11 . . 109.8 ?
    C2 N1 H11 . . 109.8 ?
    C6 N1 H12 . . 109.8 ?
    C2 N1 H12 . . 109.8 ?
    H11 N1 H12 . . 108.2 ?
    N1 C2 C3 . . 110.3(2) ?
    N1 C2 H2A . . 109.6 ?
    C3 C2 H2A . . 109.6 ?
    N1 C2 H2B . . 109.6 ?
    C3 C2 H2B . . 109.6 ?
    H2A C2 H2B . . 108.1 ?
    N4 C3 C2 . . 112.8(2) ?
    N4 C3 H3A . . 109.0 ?
    C2 C3 H3A . . 109.0 ?
    N4 C3 H3B . . 109.0 ?
    C2 C3 H3B . . 109.0 ?
    H3A C3 H3B . . 107.8 ?
    C21 N4 C3 . . 115.5(2) ?
    C21 N4 C5 . . 114.3(2) ?
    C3 N4 C5 . . 111.3(2) ?
    N4 C5 C6 . . 112.2(2) ?
    N4 C5 H5A . . 109.2 ?
    C6 C5 H5A . . 109.2 ?
    N4 C5 H5B . . 109.2 ?
    C6 C5 H5B . . 109.2 ?
    H5A C5 H5B . . 107.9 ?
    N1 C6 C5 . . 109.8(2) ?
    N1 C6 H6A . . 109.7 ?
    C5 C6 H6A . . 109.7 ?
    N1 C6 H6B . . 109.7 ?
    C5 C6 H6B . . 109.7 ?
    H6A C6 H6B . . 108.2 ?
    C26 C21 C22 . . 116.6(3) ?
    C26 C21 N4 . . 121.0(2) ?
    C22 C21 N4 . . 122.3(3) ?
    C23 C22 C21 . . 121.0(3) ?
    C23 C22 H22 . . 119.5 ?
    C21 C22 H22 . . 119.5 ?
    C24 C23 C22 . . 120.9(3) ?
    C24 C23 H23 . . 119.5 ?
    C22 C23 H23 . . 119.5 ?
    C25 C24 C23 . . 119.2(3) ?
    C25 C24 O24 . . 124.8(3) ?
    C23 C24 O24 . . 116.0(3) ?
    C24 C25 C26 . . 120.2(3) ?
    C24 C25 H25 . . 119.9 ?
    C26 C25 H25 . . 119.9 ?
    C21 C26 C25 . . 122.0(3) ?
    C21 C26 H26 . . 119.0 ?
    C25 C26 H26 . . 119.0 ?
    C24 O24 C27 . . 117.7(3) ?
    O24 C27 H27A . . 109.5 ?
    O24 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    O24 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C32 C31 C36 . . 117.2(3) ?
    C32 C31 C37 . . 121.5(3) ?
    C36 C31 C37 . . 121.3(3) ?
    C33 C32 C31 . . 121.5(3) ?
    C33 C32 H32 . . 119.3 ?
    C31 C32 H32 . . 119.3 ?
    C32 C33 C34 . . 121.0(3) ?
    C32 C33 H33 . . 119.5 ?
    C34 C33 H33 . . 119.5 ?
    C35 C34 N34 . . 121.6(3) ?
    C35 C34 C33 . . 117.4(3) ?
    N34 C34 C33 . . 121.1(3) ?
    C36 C35 C34 . . 122.0(3) ?
    C36 C35 H35 . . 119.0 ?
    C34 C35 H35 . . 119.0 ?
    C35 C36 C31 . . 120.9(3) ?
    C35 C36 H36 . . 119.5 ?
    C31 C36 H36 . . 119.5 ?
    O32 C37 O31 . . 122.9(3) ?
    O32 C37 C31 . . 118.2(3) ?
    O31 C37 C31 . . 118.9(3) ?
    C34 N34 H341 . . 122(3) ?
    C34 N34 H342 . . 115(3) ?
    H341 N34 H342 . . 117(4) ?
    H41 O41 H42 . . 104(4) ?
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 N1 C2 C3 . . . . -57.7(3) ?
    N1 C2 C3 N4 . . . . 54.8(3) ?
    C2 C3 N4 C21 . . . . 175.1(2) ?
    C2 C3 N4 C5 . . . . -52.3(3) ?
    C21 N4 C5 C6 . . . . -173.0(2) ?
    C3 N4 C5 C6 . . . . 53.8(3) ?
    C2 N1 C6 C5 . . . . 59.3(3) ?
    N4 C5 C6 N1 . . . . -57.6(3) ?
    C3 N4 C21 C26 . . . . 170.9(3) ?
    C5 N4 C21 C26 . . . . 39.7(4) ?
    C3 N4 C21 C22 . . . . -10.2(4) ?
    C5 N4 C21 C22 . . . . -141.4(3) ?
    C26 C21 C22 C23 . . . . -0.1(5) ?
    N4 C21 C22 C23 . . . . -179.0(3) ?
    C21 C22 C23 C24 . . . . -0.5(5) ?
    C22 C23 C24 C25 . . . . 1.0(5) ?
    C22 C23 C24 O24 . . . . -178.2(3) ?
    C23 C24 C25 C26 . . . . -0.8(5) ?
    O24 C24 C25 C26 . . . . 178.3(3) ?
    C22 C21 C26 C25 . . . . 0.3(5) ?
    N4 C21 C26 C25 . . . . 179.3(3) ?
    C24 C25 C26 C21 . . . . 0.1(5) ?
    C25 C24 O24 C27 . . . . -9.6(5) ?
    C23 C24 O24 C27 . . . . 169.5(4) ?
    C36 C31 C32 C33 . . . . 1.1(4) ?
    C37 C31 C32 C33 . . . . -178.0(3) ?
    C31 C32 C33 C34 . . . . 0.2(5) ?
    C32 C33 C34 C35 . . . . -1.3(5) ?
    C32 C33 C34 N34 . . . . 179.7(3) ?
    N34 C34 C35 C36 . . . . -179.8(3) ?
    C33 C34 C35 C36 . . . . 1.2(5) ?
    C34 C35 C36 C31 . . . . 0.0(5) ?
    C32 C31 C36 C35 . . . . -1.2(4) ?
    C37 C31 C36 C35 . . . . 177.9(3) ?
    C32 C31 C37 O32 . . . . -2.9(4) ?
    C36 C31 C37 O32 . . . . 178.0(3) ?
    C32 C31 C37 O31 . . . . 176.5(3) ?
    C36 C31 C37 O31 . . . . -2.6(4) ?
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
    _geom_hbond_publ_flag
    N1 H11 O41 . 0.95(2) 1.88(2) 2.803(3) 165.2(8) no
    N1 H12 O31 . 0.943(7) 1.793(18) 2.728(3) 171.2(7) no
    O41 H41 O32 2_567 0.85(3) 1.78(3) 2.631(4) 178(4) no
    O41 H42 O31 2_667 0.85(3) 1.95(3) 2.772(3) 164(3) no
    N34 H341 O24 1_556 0.82(4) 2.23(4) 3.057(4) 177(4) no
    C22 H22 Cg2 2_567 0.93 2.93 3.666(3) 137 no
    C26 H26 Cg2 2_577 0.93 2.77 3.531(3) 139 no
_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     0.964
_shelx_estimated_absorpt_T_max     0.987
_shelxl_version_number        2.014
