##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2015-06-14
_journal_date_accepted     2015-09-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue     11
_journal_page_first     o820
_journal_page_last     o821
_journal_paper_category     HO
_journal_paper_doi     10.1107/S205698901501806X
_journal_coeditor_code     JJ2193
_publ_contact_author_name     'A. Subbiah Pandi'
_publ_contact_author_address
;
Department of Physics
Presidency College
Chennai 600 005
India
;
_publ_contact_author_email     'aspandian59@gmail.com'
_publ_contact_author_fax     '044 091 2854 4894'
_publ_contact_author_phone     '044 091 24471061'
_publ_section_title
;
Crystal structure of
N-[(4-ethoxyphenyl)carbamothioyl]cyclohexanecarboxamide
;
loop_
    _publ_author_name
    _publ_author_address
    'G. Vimala'
;
Department of Physics
Presidency College (Autonomous)
Chennai 600 005
India
;
    'J. Haribabu'
;
Department of Chemistry
National Institute of Technology
Trichy 620 015
India
;
    'S. Srividya'
;
Department of Chemistry
National Institute of Technology
Trichy 620 015
India
;
    'R. Karvembu'
;
Department of Chemistry
National Institute of Technology
Trichy 620 015
India
;
    'A. SubbiahPandi'
;
Department of Physics
Presidency College (Autonomous)
Chennai 600 005
India
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1427899'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
N-[(4-Ethoxyphenyl)carbamothioyl]cyclohexanecarboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H22 N2 O2 S'
_chemical_formula_sum     'C16 H22 N2 O2 S'
_chemical_formula_iupac     'C16 H22 N2 O2 S'
_chemical_formula_weight     306.41
_chemical_melting_point     ?
_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.
;
_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     10.2273(7)
_cell_length_b     12.0946(7)
_cell_length_c     15.2099(10)
_cell_angle_alpha     70.792(3)
_cell_angle_beta     89.100(3)
_cell_angle_gamma     69.737(3)
_cell_volume     1656.42(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3444
_cell_measurement_theta_min     2.295
_cell_measurement_theta_max     25.000
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.300
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.229
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.201
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_shelx_estimated_absorpt_T_min     0.942
_shelx_estimated_absorpt_T_max     0.961
_exptl_absorpt_correction_T_min     0.942
_exptl_absorpt_correction_T_max     0.961
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'ω and φ scan'
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     35699
_diffrn_reflns_av_R_equivalents     0.0491
_diffrn_reflns_theta_min     2.295
_diffrn_reflns_theta_max     25.000
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details     ?
_reflns_number_total     5827
_reflns_number_gt     3444
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1174
_refine_ls_R_factor_gt     0.0602
_refine_ls_wR_factor_gt     0.1452
_refine_ls_wR_factor_ref     0.2051
_refine_ls_goodness_of_fit_ref     1.097
_refine_ls_restrained_S_all     1.112
_refine_ls_number_reflns     5827
_refine_ls_number_parameters     503
_refine_ls_number_restraints     97
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0708P)²+1.8566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.008
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.382
_refine_diff_density_min     -0.306
_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
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
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 C3A 0.6065(5) 0.4664(5) 0.6568(3) 0.0699(12) Uani d 1 . .
    C C4A 0.6435(5) 0.3687(4) 0.7381(3) 0.0724(12) Uani d 1 . .
    H H4A 0.7200 0.2965 0.7433 0.087 Uiso calc 1 . .
    C C5A 0.5696(4) 0.3749(4) 0.8131(3) 0.0641(11) Uani d 1 . .
    H H5A 0.5961 0.3065 0.8687 0.077 Uiso calc 1 . .
    C C6A 0.4571(4) 0.4806(4) 0.8074(3) 0.0538(9) Uani d 1 . .
    C C7A 0.4174(5) 0.5790(4) 0.7246(3) 0.0747(13) Uani d 1 . .
    H H7A 0.3398 0.6505 0.7191 0.090 Uiso calc 1 . .
    C C8A 0.4926(5) 0.5725(5) 0.6489(3) 0.0802(14) Uani d 1 . .
    H H8A 0.4661 0.6400 0.5927 0.096 Uiso calc 1 . .
    C C9A 0.3402(4) 0.5683(3) 0.9253(2) 0.0513(9) Uani d 1 . .
    C C10A 0.2564(4) 0.4308(4) 1.0544(3) 0.0568(10) Uani d 1 . .
    C C11A 0.1943(6) 0.4272(7) 1.1454(4) 0.0594(14) Uani d 0.841(10) A 5
    H H11A 0.1917 0.5013 1.1595 0.071 Uiso calc 0.841(10) A 5
    C C12A 0.2760(7) 0.3116(8) 1.2256(4) 0.091(2) Uani d 0.841(10) A 5
    H H12A 0.3716 0.3079 1.2331 0.109 Uiso calc 0.841(10) A 5
    H H12B 0.2788 0.2379 1.2120 0.109 Uiso calc 0.841(10) A 5
    C C13A 0.2113(7) 0.3106(9) 1.3156(4) 0.102(2) Uani d 0.841(10) A 5
    H H13A 0.2632 0.2328 1.3655 0.122 Uiso calc 0.841(10) A 5
    H H13B 0.2169 0.3796 1.3327 0.122 Uiso calc 0.841(10) A 5
    C C14A 0.0626(13) 0.3229(14) 1.3048(7) 0.101(3) Uani d 0.841(10) A 5
    H H14A 0.0224 0.3236 1.3629 0.121 Uiso calc 0.841(10) A 5
    H H14B 0.0575 0.2513 1.2916 0.121 Uiso calc 0.841(10) A 5
    C C15A -0.0204(7) 0.4420(9) 1.2265(4) 0.111(3) Uani d 0.841(10) A 5
    H H15A -0.0160 0.5146 1.2386 0.134 Uiso calc 0.841(10) A 5
    H H15B -0.1179 0.4502 1.2204 0.134 Uiso calc 0.841(10) A 5
    C C16A 0.0492(7) 0.4315(11) 1.1333(5) 0.127(4) Uani d 0.841(10) A 5
    H H16A 0.0498 0.3560 1.1235 0.153 Uiso calc 0.841(10) A 5
    H H16B -0.0037 0.5035 1.0794 0.153 Uiso calc 0.841(10) A 5
    C C11' 0.157(3) 0.446(5) 1.1254(18) 0.0594(14) Uani d 0.159(10) A 6
    H H11' 0.1460 0.5334 1.1146 0.071 Uiso calc 0.159(10) A 6
    C C12' 0.249(3) 0.394(4) 1.2150(19) 0.080(9) Uani d 0.159(10) A 6
    H H12C 0.3113 0.4397 1.2124 0.096 Uiso calc 0.159(10) A 6
    H H12D 0.3051 0.3061 1.2282 0.096 Uiso calc 0.159(10) A 6
    C C13' 0.148(4) 0.410(4) 1.291(3) 0.095(10) Uani d 0.159(10) A 6
    H H13C 0.2041 0.3842 1.3503 0.114 Uiso calc 0.159(10) A 6
    H H13D 0.0920 0.4985 1.2748 0.114 Uiso calc 0.159(10) A 6
    C C14' 0.049(6) 0.337(5) 1.306(3) 0.072(9) Uani d 0.159(10) A 6
    H H14C 0.1025 0.2479 1.3339 0.087 Uiso calc 0.159(10) A 6
    H H14D -0.0174 0.3617 1.3485 0.087 Uiso calc 0.159(10) A 6
    C C15' -0.029(3) 0.363(2) 1.213(2) 0.070(7) Uani d 0.159(10) A 6
    H H15C -0.0033 0.2885 1.1965 0.084 Uiso calc 0.159(10) A 6
    H H15D -0.1297 0.3958 1.2151 0.084 Uiso calc 0.159(10) A 6
    C C16' 0.020(3) 0.461(2) 1.147(2) 0.056(5) Uani d 0.159(10) A 6
    H H16C -0.0363 0.4892 1.0878 0.068 Uiso calc 0.159(10) A 6
    H H16D -0.0100 0.5314 1.1695 0.068 Uiso calc 0.159(10) A 6
    C C3B -0.4223(6) 0.9039(7) 0.1897(4) 0.0888(16) Uani d 1 . .
    C C4B -0.3314(6) 0.7967(5) 0.1788(3) 0.0853(15) Uani d 1 . .
    H H4B -0.3251 0.7187 0.2209 0.102 Uiso calc 1 . .
    C C5B -0.2503(5) 0.8033(4) 0.1071(3) 0.0706(12) Uani d 1 . .
    H H5B -0.1893 0.7299 0.1000 0.085 Uiso calc 1 . .
    C C6B -0.2580(4) 0.9180(4) 0.0450(3) 0.0543(9) Uani d 1 . .
    C C7B -0.3527(4) 1.0252(4) 0.0530(3) 0.0680(11) Uani d 1 . .
    H H7B -0.3611 1.1029 0.0096 0.082 Uiso calc 1 . .
    C C8B -0.4358(5) 1.0185(5) 0.1255(4) 0.0831(14) Uani d 1 . .
    H H8B -0.5007 1.0915 0.1307 0.100 Uiso calc 1 . .
    C C9B -0.0343(4) 0.8755(3) -0.0218(2) 0.0530(9) Uani d 1 . .
    C C10B -0.0317(5) 0.9956(4) -0.1891(3) 0.0596(10) Uani d 1 . .
    C C11B 0.0708(4) 1.0160(4) -0.2589(3) 0.0645(11) Uani d 1 . .
    H H11B 0.1621 0.9908 -0.2238 0.077 Uiso calc 1 . .
    C C12B 0.0870(6) 0.9341(4) -0.3166(3) 0.0835(14) Uani d 1 . .
    H H12E -0.0036 0.9536 -0.3488 0.100 Uiso calc 1 . .
    H H12F 0.1195 0.8470 -0.2757 0.100 Uiso calc 1 . .
    C C13B 0.1893(7) 0.9515(6) -0.3879(4) 0.118(2) Uani d 1 . .
    H H13E 0.2826 0.9221 -0.3559 0.142 Uiso calc 1 . .
    H H13F 0.1914 0.9017 -0.4270 0.142 Uiso calc 1 . .
    C C14B 0.1479(7) 1.0875(6) -0.4484(4) 0.111(2) Uani d 1 . .
    H H14E 0.2193 1.0971 -0.4899 0.133 Uiso calc 1 . .
    H H14F 0.0605 1.1132 -0.4868 0.133 Uiso calc 1 . .
    C C15B 0.1305(7) 1.1697(5) -0.3922(4) 0.1058(19) Uani d 1 . .
    H H15E 0.0968 1.2566 -0.4337 0.127 Uiso calc 1 . .
    H H15F 0.2210 1.1518 -0.3607 0.127 Uiso calc 1 . .
    C C16B 0.0288(6) 1.1527(4) -0.3196(3) 0.0879(15) Uani d 1 . .
    H H16E 0.0279 1.2023 -0.2806 0.106 Uiso calc 1 . .
    H H16F -0.0651 1.1823 -0.3508 0.106 Uiso calc 1 . .
    N N1A 0.3837(3) 0.4788(3) 0.8879(2) 0.0570(8) Uani d 1 . .
    N N2A 0.2747(3) 0.5405(3) 1.0059(2) 0.0529(8) Uani d 1 . .
    N N1B -0.1730(3) 0.9287(3) -0.0299(2) 0.0571(8) Uani d 1 . .
    N N2B 0.0275(4) 0.9065(3) -0.1033(2) 0.0576(9) Uani d 1 . .
    O O2A 0.2912(3) 0.3411(3) 1.0280(2) 0.0735(8) Uani d 1 . .
    O O2B -0.1578(3) 1.0514(3) -0.20668(19) 0.0787(9) Uani d 1 . .
    S S1A 0.36072(12) 0.70593(10) 0.88640(8) 0.0664(3) Uani d 1 . .
    S S1B 0.06988(12) 0.78100(10) 0.07648(7) 0.0643(3) Uani d 1 . .
    C C1A 0.7842(10) 0.5119(10) 0.4461(6) 0.102(3) Uani d 0.867(13) B 1
    H H1A 0.8710 0.5065 0.4736 0.153 Uiso calc 0.867(13) B 1
    H H1B 0.7622 0.5724 0.3838 0.153 Uiso calc 0.867(13) B 1
    H H1C 0.7928 0.4313 0.4439 0.153 Uiso calc 0.867(13) B 1
    C C2A 0.6698(8) 0.5516(6) 0.5040(4) 0.087(2) Uani d 0.867(13) B 1
    H H2A 0.6723 0.6239 0.5174 0.104 Uiso calc 0.867(13) B 1
    H H2B 0.5790 0.5741 0.4707 0.104 Uiso calc 0.867(13) B 1
    O O1A 0.6919(7) 0.4496(5) 0.5875(3) 0.089(2) Uani d 0.867(13) B 1
    C C1A' 0.800(13) 0.453(7) 0.457(6) 0.24(7) Uani d 0.133(13) B 2
    H H1'1 0.8898 0.3905 0.4595 0.354 Uiso calc 0.133(13) B 2
    H H1'2 0.7327 0.4499 0.4161 0.354 Uiso calc 0.133(13) B 2
    H H1'3 0.8071 0.5348 0.4351 0.354 Uiso calc 0.133(13) B 2
    C C2A' 0.754(4) 0.429(5) 0.554(4) 0.12(2) Uani d 0.133(13) B 2
    H H2'1 0.7514 0.3448 0.5758 0.141 Uiso calc 0.133(13) B 2
    H H2'2 0.8256 0.4294 0.5947 0.141 Uiso calc 0.133(13) B 2
    O O1A' 0.625(3) 0.512(4) 0.5633(14) 0.113(19) Uani d 0.133(13) B 2
    C C1B -0.608(2) 0.913(3) 0.3917(12) 0.162(10) Uani d 0.705(13) C 3
    H H1D -0.6418 0.8479 0.3911 0.243 Uiso calc 0.705(13) C 3
    H H1E -0.6811 0.9766 0.4070 0.243 Uiso calc 0.705(13) C 3
    H H1F -0.5282 0.8774 0.4377 0.243 Uiso calc 0.705(13) C 3
    C C2B -0.5672(9) 0.9695(9) 0.2959(8) 0.096(3) Uani d 0.705(13) C 3
    H H2D -0.6494 1.0189 0.2505 0.115 Uiso calc 0.705(13) C 3
    H H2E -0.5159 1.0228 0.2981 0.115 Uiso calc 0.705(13) C 3
    O O1B -0.4816(6) 0.8658(7) 0.2729(5) 0.094(2) Uani d 0.705(13) C 3
    O O1B' -0.5264(13) 0.9542(12) 0.2458(8) 0.077(5) Uani d 0.295(13) C 4
    C C1B' -0.622(3) 0.897(6) 0.391(2) 0.094(12) Uani d 0.295(13) C 4
    H H1G -0.7127 0.8934 0.3821 0.141 Uiso calc 0.295(13) C 4
    H H1H -0.6312 0.9823 0.3809 0.141 Uiso calc 0.295(13) C 4
    H H1I -0.5803 0.8455 0.4542 0.141 Uiso calc 0.295(13) C 4
    C C2B' -0.530(2) 0.8499(16) 0.3233(12) 0.076(6) Uani d 0.295(13) C 4
    H H2F -0.4355 0.7989 0.3542 0.091 Uiso calc 0.295(13) C 4
    H H2G -0.5661 0.7982 0.3015 0.091 Uiso calc 0.295(13) C 4
    H H3 -0.208(4) 0.983(3) -0.0843(17) 0.064(12) Uiso d 1 . .
    H H1 0.373(4) 0.409(2) 0.920(3) 0.069(13) Uiso d 1 . .
    H H4 0.115(2) 0.868(3) -0.094(2) 0.052(11) Uiso d 1 . .
    H H2 0.259(7) 0.612(3) 1.011(4) 0.18(3) Uiso d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    C3A C4A . 1.346(6) ?
    C3A C8A . 1.373(6) ?
    C3A O1A . 1.381(6) ?
    C3A O1A' . 1.383(19) ?
    C4A C5A . 1.366(5) ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.370(5) ?
    C5A H5A . 0.9300 ?
    C6A C7A . 1.364(5) ?
    C6A N1A . 1.423(5) ?
    C7A C8A . 1.384(6) ?
    C7A H7A . 0.9300 ?
    C8A H8A . 0.9300 ?
    C9A N1A . 1.326(5) ?
    C9A N2A . 1.387(4) ?
    C9A S1A . 1.659(4) ?
    C10A O2A . 1.216(4) ?
    C10A N2A . 1.366(5) ?
    C10A C11' . 1.482(17) ?
    C10A C11A . 1.508(6) ?
    C11A C16A . 1.479(8) ?
    C11A C12A . 1.497(7) ?
    C11A H11A . 0.9800 ?
    C12A C13A . 1.510(7) ?
    C12A H12A . 0.9700 ?
    C12A H12B . 0.9700 ?
    C13A C14A . 1.482(11) ?
    C13A H13A . 0.9700 ?
    C13A H13B . 0.9700 ?
    C14A C15A . 1.506(12) ?
    C14A H14A . 0.9700 ?
    C14A H14B . 0.9700 ?
    C15A C16A . 1.599(9) ?
    C15A H15A . 0.9700 ?
    C15A H15B . 0.9700 ?
    C16A H16A . 0.9700 ?
    C16A H16B . 0.9700 ?
    C11' C16' . 1.402(18) ?
    C11' C12' . 1.485(19) ?
    C11' H11' . 0.9800 ?
    C12' C13' . 1.555(19) ?
    C12' H12C . 0.9700 ?
    C12' H12D . 0.9700 ?
    C13' C14' . 1.53(2) ?
    C13' H13C . 0.9700 ?
    C13' H13D . 0.9700 ?
    C14' C15' . 1.51(2) ?
    C14' H14C . 0.9700 ?
    C14' H14D . 0.9700 ?
    C15' C16' . 1.505(19) ?
    C15' H15C . 0.9700 ?
    C15' H15D . 0.9700 ?
    C16' H16C . 0.9700 ?
    C16' H16D . 0.9700 ?
    C3B C4B . 1.369(7) ?
    C3B C8B . 1.370(7) ?
    C3B O1B . 1.403(7) ?
    C3B O1B' . 1.448(12) ?
    C4B C5B . 1.358(6) ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.373(5) ?
    C5B H5B . 0.9300 ?
    C6B C7B . 1.366(5) ?
    C6B N1B . 1.421(5) ?
    C7B C8B . 1.379(6) ?
    C7B H7B . 0.9300 ?
    C8B H8B . 0.9300 ?
    C9B N1B . 1.328(5) ?
    C9B N2B . 1.382(5) ?
    C9B S1B . 1.661(4) ?
    C10B O2B . 1.217(5) ?
    C10B N2B . 1.371(5) ?
    C10B C11B . 1.502(5) ?
    C11B C12B . 1.494(6) ?
    C11B C16B . 1.512(6) ?
    C11B H11B . 0.9800 ?
    C12B C13B . 1.510(6) ?
    C12B H12E . 0.9700 ?
    C12B H12F . 0.9700 ?
    C13B C14B . 1.505(7) ?
    C13B H13E . 0.9700 ?
    C13B H13F . 0.9700 ?
    C14B C15B . 1.479(8) ?
    C14B H14E . 0.9700 ?
    C14B H14F . 0.9700 ?
    C15B C16B . 1.519(7) ?
    C15B H15E . 0.9700 ?
    C15B H15F . 0.9700 ?
    C16B H16E . 0.9700 ?
    C16B H16F . 0.9700 ?
    N1A H1 . 0.871(19) ?
    N2A H2 . 0.85(2) ?
    N1B H3 . 0.855(19) ?
    N2B H4 . 0.841(18) ?
    C1A C2A . 1.493(9) ?
    C1A H1A . 0.9600 ?
    C1A H1B . 0.9600 ?
    C1A H1C . 0.9600 ?
    C2A O1A . 1.404(7) ?
    C2A H2A . 0.9700 ?
    C2A H2B . 0.9700 ?
    C1A' C2A' . 1.49(2) ?
    C1A' H1'1 . 0.9600 ?
    C1A' H1'2 . 0.9600 ?
    C1A' H1'3 . 0.9600 ?
    C2A' O1A' . 1.40(2) ?
    C2A' H2'1 . 0.9700 ?
    C2A' H2'2 . 0.9700 ?
    C1B C2B . 1.515(17) ?
    C1B H1D . 0.9600 ?
    C1B H1E . 0.9600 ?
    C1B H1F . 0.9600 ?
    C2B O1B . 1.408(9) ?
    C2B H2D . 0.9700 ?
    C2B H2E . 0.9700 ?
    O1B' C2B' . 1.426(15) ?
    C1B' C2B' . 1.51(2) ?
    C1B' H1G . 0.9600 ?
    C1B' H1H . 0.9600 ?
    C1B' H1I . 0.9600 ?
    C2B' H2F . 0.9700 ?
    C2B' H2G . 0.9700 ?
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
    C4A C3A C8A . . 119.7(4) ?
    C4A C3A O1A . . 114.8(4) ?
    C8A C3A O1A . . 125.5(5) ?
    C4A C3A O1A' . . 147.5(17) ?
    C8A C3A O1A' . . 92.4(16) ?
    C3A C4A C5A . . 120.5(4) ?
    C3A C4A H4A . . 119.7 ?
    C5A C4A H4A . . 119.7 ?
    C4A C5A C6A . . 120.9(4) ?
    C4A C5A H5A . . 119.6 ?
    C6A C5A H5A . . 119.6 ?
    C7A C6A C5A . . 118.8(4) ?
    C7A C6A N1A . . 123.6(3) ?
    C5A C6A N1A . . 117.5(3) ?
    C6A C7A C8A . . 120.1(4) ?
    C6A C7A H7A . . 119.9 ?
    C8A C7A H7A . . 119.9 ?
    C3A C8A C7A . . 119.9(4) ?
    C3A C8A H8A . . 120.1 ?
    C7A C8A H8A . . 120.1 ?
    N1A C9A N2A . . 115.5(3) ?
    N1A C9A S1A . . 126.3(3) ?
    N2A C9A S1A . . 118.2(3) ?
    O2A C10A N2A . . 122.9(4) ?
    O2A C10A C11' . . 123(2) ?
    N2A C10A C11' . . 112(2) ?
    O2A C10A C11A . . 122.2(4) ?
    N2A C10A C11A . . 114.9(4) ?
    C16A C11A C12A . . 109.2(6) ?
    C16A C11A C10A . . 108.1(5) ?
    C12A C11A C10A . . 112.5(5) ?
    C16A C11A H11A . . 109.0 ?
    C12A C11A H11A . . 109.0 ?
    C10A C11A H11A . . 109.0 ?
    C11A C12A C13A . . 111.3(5) ?
    C11A C12A H12A . . 109.4 ?
    C13A C12A H12A . . 109.4 ?
    C11A C12A H12B . . 109.4 ?
    C13A C12A H12B . . 109.4 ?
    H12A C12A H12B . . 108.0 ?
    C14A C13A C12A . . 110.6(7) ?
    C14A C13A H13A . . 109.5 ?
    C12A C13A H13A . . 109.5 ?
    C14A C13A H13B . . 109.5 ?
    C12A C13A H13B . . 109.5 ?
    H13A C13A H13B . . 108.1 ?
    C13A C14A C15A . . 110.8(7) ?
    C13A C14A H14A . . 109.5 ?
    C15A C14A H14A . . 109.5 ?
    C13A C14A H14B . . 109.5 ?
    C15A C14A H14B . . 109.5 ?
    H14A C14A H14B . . 108.1 ?
    C14A C15A C16A . . 106.3(10) ?
    C14A C15A H15A . . 110.5 ?
    C16A C15A H15A . . 110.5 ?
    C14A C15A H15B . . 110.5 ?
    C16A C15A H15B . . 110.5 ?
    H15A C15A H15B . . 108.7 ?
    C11A C16A C15A . . 107.4(7) ?
    C11A C16A H16A . . 110.2 ?
    C15A C16A H16A . . 110.2 ?
    C11A C16A H16B . . 110.2 ?
    C15A C16A H16B . . 110.2 ?
    H16A C16A H16B . . 108.5 ?
    C16' C11' C10A . . 146(3) ?
    C16' C11' C12' . . 108(2) ?
    C10A C11' C12' . . 104.1(17) ?
    C16' C11' H11' . . 94.8 ?
    C10A C11' H11' . . 94.8 ?
    C12' C11' H11' . . 94.8 ?
    C11' C12' C13' . . 106(2) ?
    C11' C12' H12C . . 110.6 ?
    C13' C12' H12C . . 110.6 ?
    C11' C12' H12D . . 110.6 ?
    C13' C12' H12D . . 110.6 ?
    H12C C12' H12D . . 108.8 ?
    C14' C13' C12' . . 116(4) ?
    C14' C13' H13C . . 108.3 ?
    C12' C13' H13C . . 108.3 ?
    C14' C13' H13D . . 108.3 ?
    C12' C13' H13D . . 108.3 ?
    H13C C13' H13D . . 107.4 ?
    C15' C14' C13' . . 110(3) ?
    C15' C14' H14C . . 109.6 ?
    C13' C14' H14C . . 109.6 ?
    C15' C14' H14D . . 109.6 ?
    C13' C14' H14D . . 109.6 ?
    H14C C14' H14D . . 108.1 ?
    C16' C15' C14' . . 102(3) ?
    C16' C15' H15C . . 111.4 ?
    C14' C15' H15C . . 111.4 ?
    C16' C15' H15D . . 111.4 ?
    C14' C15' H15D . . 111.4 ?
    H15C C15' H15D . . 109.2 ?
    C11' C16' C15' . . 127(3) ?
    C11' C16' H16C . . 105.6 ?
    C15' C16' H16C . . 105.6 ?
    C11' C16' H16D . . 105.6 ?
    C15' C16' H16D . . 105.5 ?
    H16C C16' H16D . . 106.1 ?
    C4B C3B C8B . . 119.7(4) ?
    C4B C3B O1B . . 106.5(6) ?
    C8B C3B O1B . . 133.8(6) ?
    C4B C3B O1B' . . 145.2(7) ?
    C8B C3B O1B' . . 95.1(6) ?
    C5B C4B C3B . . 120.5(5) ?
    C5B C4B H4B . . 119.7 ?
    C3B C4B H4B . . 119.7 ?
    C4B C5B C6B . . 120.2(4) ?
    C4B C5B H5B . . 119.9 ?
    C6B C5B H5B . . 119.9 ?
    C7B C6B C5B . . 119.6(4) ?
    C7B C6B N1B . . 118.5(4) ?
    C5B C6B N1B . . 121.8(4) ?
    C6B C7B C8B . . 120.2(4) ?
    C6B C7B H7B . . 119.9 ?
    C8B C7B H7B . . 119.9 ?
    C3B C8B C7B . . 119.7(5) ?
    C3B C8B H8B . . 120.2 ?
    C7B C8B H8B . . 120.2 ?
    N1B C9B N2B . . 115.7(3) ?
    N1B C9B S1B . . 126.3(3) ?
    N2B C9B S1B . . 117.9(3) ?
    O2B C10B N2B . . 121.7(4) ?
    O2B C10B C11B . . 123.5(3) ?
    N2B C10B C11B . . 114.7(4) ?
    C12B C11B C10B . . 110.1(4) ?
    C12B C11B C16B . . 111.5(4) ?
    C10B C11B C16B . . 111.7(4) ?
    C12B C11B H11B . . 107.8 ?
    C10B C11B H11B . . 107.8 ?
    C16B C11B H11B . . 107.8 ?
    C11B C12B C13B . . 112.0(4) ?
    C11B C12B H12E . . 109.2 ?
    C13B C12B H12E . . 109.2 ?
    C11B C12B H12F . . 109.2 ?
    C13B C12B H12F . . 109.2 ?
    H12E C12B H12F . . 107.9 ?
    C14B C13B C12B . . 110.8(5) ?
    C14B C13B H13E . . 109.5 ?
    C12B C13B H13E . . 109.5 ?
    C14B C13B H13F . . 109.5 ?
    C12B C13B H13F . . 109.5 ?
    H13E C13B H13F . . 108.1 ?
    C15B C14B C13B . . 112.1(5) ?
    C15B C14B H14E . . 109.2 ?
    C13B C14B H14E . . 109.2 ?
    C15B C14B H14F . . 109.2 ?
    C13B C14B H14F . . 109.2 ?
    H14E C14B H14F . . 107.9 ?
    C14B C15B C16B . . 112.7(5) ?
    C14B C15B H15E . . 109.1 ?
    C16B C15B H15E . . 109.1 ?
    C14B C15B H15F . . 109.1 ?
    C16B C15B H15F . . 109.1 ?
    H15E C15B H15F . . 107.8 ?
    C11B C16B C15B . . 110.6(4) ?
    C11B C16B H16E . . 109.5 ?
    C15B C16B H16E . . 109.5 ?
    C11B C16B H16F . . 109.5 ?
    C15B C16B H16F . . 109.5 ?
    H16E C16B H16F . . 108.1 ?
    C9A N1A C6A . . 127.3(3) ?
    C9A N1A H1 . . 115(3) ?
    C6A N1A H1 . . 118(3) ?
    C10A N2A C9A . . 128.4(3) ?
    C10A N2A H2 . . 138(3) ?
    C9A N2A H2 . . 93(2) ?
    C9B N1B C6B . . 125.7(3) ?
    C9B N1B H3 . . 113(3) ?
    C6B N1B H3 . . 120(3) ?
    C10B N2B C9B . . 129.1(3) ?
    C10B N2B H4 . . 119(3) ?
    C9B N2B H4 . . 112(3) ?
    C2A C1A H1A . . 109.5 ?
    C2A C1A H1B . . 109.5 ?
    H1A C1A H1B . . 109.5 ?
    C2A C1A H1C . . 109.5 ?
    H1A C1A H1C . . 109.5 ?
    H1B C1A H1C . . 109.5 ?
    O1A C2A C1A . . 107.2(7) ?
    O1A C2A H2A . . 110.3 ?
    C1A C2A H2A . . 110.3 ?
    O1A C2A H2B . . 110.3 ?
    C1A C2A H2B . . 110.3 ?
    H2A C2A H2B . . 108.5 ?
    C3A O1A C2A . . 118.4(6) ?
    C2A' C1A' H1'1 . . 109.5 ?
    C2A' C1A' H1'2 . . 109.5 ?
    H1'1 C1A' H1'2 . . 109.5 ?
    C2A' C1A' H1'3 . . 109.5 ?
    H1'1 C1A' H1'3 . . 109.5 ?
    H1'2 C1A' H1'3 . . 109.5 ?
    O1A' C2A' C1A' . . 117(5) ?
    O1A' C2A' H2'1 . . 108.1 ?
    C1A' C2A' H2'1 . . 108.0 ?
    O1A' C2A' H2'2 . . 108.0 ?
    C1A' C2A' H2'2 . . 108.1 ?
    H2'1 C2A' H2'2 . . 107.3 ?
    C3A O1A' C2A' . . 105(4) ?
    C2B C1B H1D . . 109.5 ?
    C2B C1B H1E . . 109.5 ?
    H1D C1B H1E . . 109.5 ?
    C2B C1B H1F . . 109.5 ?
    H1D C1B H1F . . 109.5 ?
    H1E C1B H1F . . 109.5 ?
    O1B C2B C1B . . 104.7(14) ?
    O1B C2B H2D . . 110.8 ?
    C1B C2B H2D . . 110.8 ?
    O1B C2B H2E . . 110.8 ?
    C1B C2B H2E . . 110.8 ?
    H2D C2B H2E . . 108.9 ?
    C3B O1B C2B . . 111.4(8) ?
    C2B' O1B' C3B . . 106.7(14) ?
    C2B' C1B' H1G . . 109.5 ?
    C2B' C1B' H1H . . 109.5 ?
    H1G C1B' H1H . . 109.5 ?
    C2B' C1B' H1I . . 109.5 ?
    H1G C1B' H1I . . 109.5 ?
    H1H C1B' H1I . . 109.5 ?
    O1B' C2B' C1B' . . 109(3) ?
    O1B' C2B' H2F . . 109.8 ?
    C1B' C2B' H2F . . 109.8 ?
    O1B' C2B' H2G . . 109.8 ?
    C1B' C2B' H2G . . 109.8 ?
    H2F C2B' H2G . . 108.3 ?
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
    C8A C3A C4A C5A . . . . -0.7(7) ?
    O1A C3A C4A C5A . . . . 178.3(5) ?
    O1A' C3A C4A C5A . . . . -171(4) ?
    C3A C4A C5A C6A . . . . -0.4(7) ?
    C4A C5A C6A C7A . . . . 1.6(7) ?
    C4A C5A C6A N1A . . . . 178.7(4) ?
    C5A C6A C7A C8A . . . . -1.7(7) ?
    N1A C6A C7A C8A . . . . -178.6(4) ?
    C4A C3A C8A C7A . . . . 0.6(8) ?
    O1A C3A C8A C7A . . . . -178.2(5) ?
    O1A' C3A C8A C7A . . . . 175(2) ?
    C6A C7A C8A C3A . . . . 0.6(8) ?
    O2A C10A C11A C16A . . . . -73.2(7) ?
    N2A C10A C11A C16A . . . . 108.9(7) ?
    O2A C10A C11A C12A . . . . 47.5(8) ?
    N2A C10A C11A C12A . . . . -130.4(6) ?
    C16A C11A C12A C13A . . . . -59.9(9) ?
    C10A C11A C12A C13A . . . . -180.0(6) ?
    C11A C12A C13A C14A . . . . 56.1(10) ?
    C12A C13A C14A C15A . . . . -58.2(13) ?
    C13A C14A C15A C16A . . . . 61.0(13) ?
    C12A C11A C16A C15A . . . . 63.0(11) ?
    C10A C11A C16A C15A . . . . -174.2(8) ?
    C14A C15A C16A C11A . . . . -63.5(11) ?
    O2A C10A C11' C16' . . . . -63(7) ?
    N2A C10A C11' C16' . . . . 101(7) ?
    O2A C10A C11' C12' . . . . 95(3) ?
    N2A C10A C11' C12' . . . . -101(3) ?
    C16' C11' C12' C13' . . . . -14(5) ?
    C10A C11' C12' C13' . . . . 179(3) ?
    C11' C12' C13' C14' . . . . 63(5) ?
    C12' C13' C14' C15' . . . . -52(6) ?
    C13' C14' C15' C16' . . . . -4(5) ?
    C10A C11' C16' C15' . . . . 105(7) ?
    C12' C11' C16' C15' . . . . -52(6) ?
    C14' C15' C16' C11' . . . . 63(5) ?
    C8B C3B C4B C5B . . . . 2.8(8) ?
    O1B C3B C4B C5B . . . . -175.7(5) ?
    O1B' C3B C4B C5B . . . . 179.8(12) ?
    C3B C4B C5B C6B . . . . 0.5(7) ?
    C4B C5B C6B C7B . . . . -3.2(7) ?
    C4B C5B C6B N1B . . . . 178.8(4) ?
    C5B C6B C7B C8B . . . . 2.7(7) ?
    N1B C6B C7B C8B . . . . -179.2(4) ?
    C4B C3B C8B C7B . . . . -3.2(8) ?
    O1B C3B C8B C7B . . . . 174.8(6) ?
    O1B' C3B C8B C7B . . . . 178.5(7) ?
    C6B C7B C8B C3B . . . . 0.5(7) ?
    O2B C10B C11B C12B . . . . -86.4(5) ?
    N2B C10B C11B C12B . . . . 92.4(5) ?
    O2B C10B C11B C16B . . . . 38.1(6) ?
    N2B C10B C11B C16B . . . . -143.2(4) ?
    C10B C11B C12B C13B . . . . 180.0(4) ?
    C16B C11B C12B C13B . . . . 55.4(6) ?
    C11B C12B C13B C14B . . . . -54.8(7) ?
    C12B C13B C14B C15B . . . . 54.1(8) ?
    C13B C14B C15B C16B . . . . -54.3(7) ?
    C12B C11B C16B C15B . . . . -53.8(6) ?
    C10B C11B C16B C15B . . . . -177.5(4) ?
    C14B C15B C16B C11B . . . . 53.7(7) ?
    N2A C9A N1A C6A . . . . -178.0(3) ?
    S1A C9A N1A C6A . . . . 0.3(6) ?
    C7A C6A N1A C9A . . . . -47.9(6) ?
    C5A C6A N1A C9A . . . . 135.1(4) ?
    O2A C10A N2A C9A . . . . -4.3(7) ?
    C11' C10A N2A C9A . . . . -168.6(14) ?
    C11A C10A N2A C9A . . . . 173.6(4) ?
    N1A C9A N2A C10A . . . . 4.1(6) ?
    S1A C9A N2A C10A . . . . -174.4(3) ?
    N2B C9B N1B C6B . . . . -175.4(3) ?
    S1B C9B N1B C6B . . . . 2.4(6) ?
    C7B C6B N1B C9B . . . . 128.5(4) ?
    C5B C6B N1B C9B . . . . -53.5(6) ?
    O2B C10B N2B C9B . . . . -9.1(7) ?
    C11B C10B N2B C9B . . . . 172.1(4) ?
    N1B C9B N2B C10B . . . . 8.7(6) ?
    S1B C9B N2B C10B . . . . -169.2(3) ?
    C4A C3A O1A C2A . . . . -173.4(6) ?
    C8A C3A O1A C2A . . . . 5.5(10) ?
    C1A C2A O1A C3A . . . . 174.4(6) ?
    C4A C3A O1A' C2A' . . . . -19(7) ?
    C8A C3A O1A' C2A' . . . . 170(4) ?
    C1A' C2A' O1A' C3A . . . . 178(6) ?
    C4B C3B O1B C2B . . . . 174.2(6) ?
    C8B C3B O1B C2B . . . . -4.0(10) ?
    C1B C2B O1B C3B . . . . -173.5(11) ?
    C4B C3B O1B' C2B' . . . . 5(2) ?
    C8B C3B O1B' C2B' . . . . -177.8(11) ?
    C3B O1B' C2B' C1B' . . . . 172.4(19) ?
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
    C2B H2D O2B 2_475 0.97 2.57 3.264(10) 128.2
    N1B H3 O2B . 0.855(19) 1.91(3) 2.641(4) 142(4)
    N1A H1 O2A . 0.871(19) 1.90(3) 2.628(4) 140(4)
    N2B H4 S1A 1_554 0.841(18) 2.68(2) 3.469(3) 157(3)
    N2A H2 S1B 1_556 0.85(2) 2.73(3) 3.430(3) 140(3)
    C12' H12C Cg1 2_667 0.90 2.49(2) 3.420(10)
                                             159
