#------------------------------------------------------------------------------
#$Date: 2020-04-09 08:07:44 +0300 (Thu, 09 Apr 2020) $
#$Revision: 250534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/20/2022004.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022004
loop_
_publ_author_name
'Zheng, Kang'
'Xie, Changjian'
'Li, Xiaowei'
'Wu, Weiwei'
'Li, Ao'
'Qian, Shaosong'
'Pang, Qiuxiang'
_publ_section_title
;
 Crystal structures, thermal stabilities, and dissolution behaviours of
 tinidazole and the tinidazole--vanillic acid cocrystal: insights from
 energy frameworks
;
_journal_coeditor_code           DG3004
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620004180
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C8 H13 N3 O4 S, C8 H8 O4'
_chemical_formula_moiety         'C8 H13 N3 O4 S, C8 H8 O4'
_chemical_formula_sum            'C16 H21 N3 O8 S'
_chemical_formula_weight         415.42
_chemical_melting_point          404
_chemical_name_common
;
Tinidazole--vanillic acid (1/1)
;
_chemical_name_systematic
;
1-(2-Ethylsulfonylethyl)-2-methyl-5-nitroimidazole;
4-hydroxy-3-methoxybenzoic acid
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                98.0780(10)
_cell_angle_beta                 97.7930(10)
_cell_angle_gamma                99.7800(10)
_cell_formula_units_Z            4
_cell_length_a                   11.1206(5)
_cell_length_b                   12.6519(6)
_cell_length_c                   13.6042(6)
_cell_measurement_reflns_used    9002
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.492
_cell_measurement_theta_min      2.438
_cell_volume                     1842.42(15)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX3 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16552
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.060
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2016; Krause et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.251
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.482
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0476P)²+0.7942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                7034
_reflns_number_total             8425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3004sup1.cif
_cod_data_source_block           TNZ-VA
_cod_database_code               2022004
_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   0.880
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.46056(14) 0.86128(12) 0.26200(12) 0.0181(3) Uani d 1 . .
C C2 -0.36794(14) 0.80378(13) 0.27192(12) 0.0196(3) Uani d 1 . .
H H2 -0.303525 0.815954 0.328133 0.024 Uiso calc 1 . .
C C3 -0.48290(14) 0.73672(13) 0.12877(12) 0.0188(3) Uani d 1 . .
C C4 -0.52869(16) 0.67038(14) 0.02743(13) 0.0255(4) Uani d 1 . .
H H4A -0.519630 0.716963 -0.023929 0.038 Uiso calc 1 . .
H H4B -0.616105 0.637473 0.022657 0.038 Uiso calc 1 . .
H H4C -0.480551 0.612898 0.016672 0.038 Uiso calc 1 . .
C C5 -0.64659(13) 0.85083(12) 0.12261(12) 0.0172(3) Uani d 1 . .
H H5A -0.696638 0.872518 0.174146 0.021 Uiso calc 1 . .
H H5B -0.697934 0.789346 0.073279 0.021 Uiso calc 1 . .
C C6 -0.60737(13) 0.94607(12) 0.06971(11) 0.0165(3) Uani d 1 . .
H H6A -0.575349 0.918946 0.008476 0.020 Uiso calc 1 . .
H H6B -0.538864 0.998278 0.114686 0.020 Uiso calc 1 . .
C C7 -0.73585(17) 1.10524(15) 0.14532(13) 0.0283(4) Uani d 1 . .
H H7A -0.755094 1.063089 0.199162 0.034 Uiso calc 1 . .
H H7B -0.655148 1.155129 0.169154 0.034 Uiso calc 1 . .
C C8 -0.83651(19) 1.17061(17) 0.12190(17) 0.0411(5) Uani d 1 . .
H H8A -0.815246 1.214412 0.070539 0.062 Uiso calc 1 . .
H H8B -0.843111 1.218652 0.183242 0.062 Uiso calc 1 . .
H H8C -0.915777 1.120736 0.096896 0.062 Uiso calc 1 . .
N N1 -0.53583(11) 0.81701(10) 0.17062(10) 0.0163(3) Uani d 1 . .
N N2 -0.38173(12) 0.72649(11) 0.18929(10) 0.0201(3) Uani d 1 . .
N N3 -0.47884(12) 0.94978(11) 0.33122(10) 0.0210(3) Uani d 1 . .
O O1 -0.39776(11) 0.98249(10) 0.40576(9) 0.0293(3) Uani d 1 . .
O O2 -0.57235(11) 0.98869(10) 0.31472(9) 0.0278(3) Uani d 1 . .
O O3 -0.84376(10) 0.93943(9) 0.00736(9) 0.0272(3) Uani d 1 . .
O O4 -0.68905(12) 1.07976(11) -0.03874(10) 0.0326(3) Uani d 1 . .
S S1 -0.72785(3) 1.01561(3) 0.03492(3) 0.01782(10) Uani d 1 . .
C C9 0.01626(14) 0.47902(12) 0.29301(12) 0.0176(3) Uani d 1 . .
C C10 -0.01500(14) 0.43286(12) 0.19089(12) 0.0178(3) Uani d 1 . .
H H10 0.026078 0.378217 0.163946 0.021 Uiso calc 1 . .
C C11 -0.10512(14) 0.46637(12) 0.12932(12) 0.0180(3) Uani d 1 . .
C C12 -0.16802(14) 0.54533(13) 0.17106(12) 0.0201(3) Uani d 1 . .
C C13 -0.13652(15) 0.58994(13) 0.27226(12) 0.0224(3) Uani d 1 . .
H H13 -0.179388 0.642736 0.300050 0.027 Uiso calc 1 . .
C C14 -0.04333(14) 0.55866(13) 0.33361(12) 0.0198(3) Uani d 1 . .
H H14 -0.020594 0.591259 0.402434 0.024 Uiso calc 1 . .
C C15 0.11253(14) 0.43973(13) 0.35574(12) 0.0196(3) Uani d 1 . .
C C16 -0.07432(15) 0.35336(13) -0.01673(12) 0.0213(3) Uani d 1 . .
H H16A 0.014440 0.384254 -0.003279 0.032 Uiso calc 1 . .
H H16B -0.102977 0.337225 -0.089567 0.032 Uiso calc 1 . .
H H16C -0.089379 0.286175 0.011607 0.032 Uiso calc 1 . .
O O5 0.15118(11) 0.35713(10) 0.32573(9) 0.0287(3) Uani d 1 . .
O O6 0.15317(11) 0.49796(10) 0.44539(8) 0.0255(3) Uani d 1 . .
H H6 0.218012 0.476315 0.474978 0.038 Uiso d 1 . .
O O7 -0.14007(10) 0.42987(9) 0.02857(8) 0.0210(2) Uani d 1 . .
O O8 -0.25695(11) 0.57457(10) 0.10785(9) 0.0292(3) Uani d 1 . .
H H8 -0.294480 0.621059 0.139295 0.044 Uiso d 1 . .
C C17 0.94304(16) -0.07560(14) 0.59092(13) 0.0244(4) Uani d 1 . .
C C18 0.85017(16) -0.01837(15) 0.59093(14) 0.0287(4) Uani d 1 . .
H H18 0.776949 -0.033059 0.542351 0.034 Uiso calc 1 . .
C C19 0.98849(15) 0.05546(13) 0.72037(13) 0.0218(3) Uani d 1 . .
C C20 1.05196(17) 0.12934(15) 0.81456(14) 0.0297(4) Uani d 1 . .
H H20A 1.020283 0.197275 0.819536 0.044 Uiso calc 1 . .
H H20B 1.141145 0.145242 0.813689 0.044 Uiso calc 1 . .
H H20C 1.036305 0.094225 0.872592 0.044 Uiso calc 1 . .
C C21 1.15235(14) -0.05841(13) 0.70510(13) 0.0219(3) Uani d 1 . .
H H21A 1.208835 0.004903 0.748481 0.026 Uiso calc 1 . .
H H21B 1.189875 -0.078320 0.644839 0.026 Uiso calc 1 . .
C C22 1.13687(14) -0.15361(13) 0.76226(12) 0.0187(3) Uani d 1 . .
H H22A 1.073486 -0.214209 0.721798 0.022 Uiso calc 1 . .
H H22B 1.107962 -0.131091 0.826266 0.022 Uiso calc 1 . .
C C23 1.27814(15) -0.30524(13) 0.68857(12) 0.0224(3) Uani d 1 . .
H H23A 1.204977 -0.363532 0.684181 0.027 Uiso calc 1 . .
H H23B 1.273367 -0.277331 0.623995 0.027 Uiso calc 1 . .
C C24 1.39617(18) -0.35043(16) 0.70807(15) 0.0340(4) Uani d 1 . .
H H24A 1.468193 -0.292072 0.713354 0.051 Uiso calc 1 . .
H H24B 1.397172 -0.408358 0.652373 0.051 Uiso calc 1 . .
H H24C 1.399039 -0.379924 0.771038 0.051 Uiso calc 1 . .
N N4 1.03218(12) -0.02863(11) 0.67403(10) 0.0204(3) Uani d 1 . .
N N5 0.87873(13) 0.06310(12) 0.67142(11) 0.0261(3) Uani d 1 . .
N N6 0.95208(15) -0.16613(13) 0.51980(11) 0.0317(4) Uani d 1 . .
O O9 0.87115(15) -0.19110(14) 0.44492(11) 0.0552(5) Uani d 1 . .
O O10 1.03764(14) -0.21426(12) 0.53472(11) 0.0448(4) Uani d 1 . .
O O11 1.27991(11) -0.24272(10) 0.88032(9) 0.0270(3) Uani d 1 . .
O O12 1.37899(10) -0.11068(9) 0.78510(10) 0.0280(3) Uani d 1 . .
S S2 1.27955(3) -0.19896(3) 0.78827(3) 0.01716(9) Uani d 1 . .
C C25 0.50219(14) 0.32744(13) 0.55299(12) 0.0195(3) Uani d 1 . .
C C26 0.55642(14) 0.39283(13) 0.64589(12) 0.0189(3) Uani d 1 . .
H H26 0.522721 0.453611 0.670389 0.023 Uiso calc 1 . .
C C27 0.65868(14) 0.36881(12) 0.70163(12) 0.0185(3) Uani d 1 . .
C C28 0.70904(14) 0.27939(13) 0.66395(12) 0.0180(3) Uani d 1 . .
C C29 0.65570(15) 0.21639(13) 0.57145(12) 0.0202(3) Uani d 1 . .
H H29 0.690715 0.156907 0.545781 0.024 Uiso calc 1 . .
C C30 0.55186(15) 0.23925(13) 0.51603(12) 0.0210(3) Uani d 1 . .
H H30 0.515016 0.194962 0.453315 0.025 Uiso calc 1 . .
C C31 0.38976(15) 0.35374(13) 0.49928(12) 0.0224(3) Uani d 1 . .
C C32 0.66986(16) 0.51617(14) 0.83451(13) 0.0270(4) Uani d 1 . .
H H32A 0.680275 0.571157 0.790708 0.040 Uiso calc 1 . .
H H32B 0.715997 0.546457 0.902031 0.040 Uiso calc 1 . .
H H32C 0.581919 0.494700 0.838347 0.040 Uiso calc 1 . .
O O13 0.34422(12) 0.29145(10) 0.41124(9) 0.0306(3) Uani d 1 . .
H H13A 0.279267 0.318603 0.384668 0.046 Uiso d 1 . .
O O14 0.34167(12) 0.42777(11) 0.53397(9) 0.0328(3) Uani d 1 . .
O O15 0.71543(11) 0.42347(9) 0.79447(9) 0.0242(3) Uani d 1 . .
O O16 0.80696(10) 0.25822(9) 0.72288(8) 0.0226(2) Uani d 1 . .
H H16 0.831837 0.197997 0.697200 0.034 Uiso d 1 . .
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'
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 C1 N1 . . 107.11(13) ?
C2 C1 N3 . . 127.29(14) ?
N1 C1 N3 . . 125.59(13) ?
N2 C2 C1 . . 109.55(13) ?
N2 C2 H2 . . 125.2 ?
C1 C2 H2 . . 125.2 ?
N2 C3 N1 . . 111.38(13) ?
N2 C3 C4 . . 124.02(14) ?
N1 C3 C4 . . 124.57(14) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N1 C5 C6 . . 109.35(12) ?
N1 C5 H5A . . 109.8 ?
C6 C5 H5A . . 109.8 ?
N1 C5 H5B . . 109.8 ?
C6 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.3 ?
C5 C6 S1 . . 113.92(10) ?
C5 C6 H6A . . 108.8 ?
S1 C6 H6A . . 108.8 ?
C5 C6 H6B . . 108.8 ?
S1 C6 H6B . . 108.8 ?
H6A C6 H6B . . 107.7 ?
C8 C7 S1 . . 109.14(13) ?
C8 C7 H7A . . 109.9 ?
S1 C7 H7A . . 109.9 ?
C8 C7 H7B . . 109.9 ?
S1 C7 H7B . . 109.9 ?
H7A C7 H7B . . 108.3 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C3 N1 C1 . . 105.70(12) ?
C3 N1 C5 . . 125.06(13) ?
C1 N1 C5 . . 129.15(13) ?
C3 N2 C2 . . 106.23(13) ?
O2 N3 O1 . . 124.08(14) ?
O2 N3 C1 . . 119.59(13) ?
O1 N3 C1 . . 116.33(13) ?
O4 S1 O3 . . 117.56(8) ?
O4 S1 C6 . . 107.18(7) ?
O3 S1 C6 . . 109.72(7) ?
O4 S1 C7 . . 108.38(9) ?
O3 S1 C7 . . 107.94(8) ?
C6 S1 C7 . . 105.41(8) ?
C14 C9 C10 . . 120.52(14) ?
C14 C9 C15 . . 121.30(14) ?
C10 C9 C15 . . 118.17(14) ?
C11 C10 C9 . . 120.32(14) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
O7 C11 C10 . . 125.34(14) ?
O7 C11 C12 . . 115.45(13) ?
C10 C11 C12 . . 119.21(14) ?
O8 C12 C13 . . 123.13(14) ?
O8 C12 C11 . . 117.04(14) ?
C13 C12 C11 . . 119.82(14) ?
C12 C13 C14 . . 121.00(15) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C13 C14 C9 . . 119.08(14) ?
C13 C14 H14 . . 120.5 ?
C9 C14 H14 . . 120.5 ?
O5 C15 O6 . . 122.59(14) ?
O5 C15 C9 . . 121.99(14) ?
O6 C15 C9 . . 115.42(13) ?
O7 C16 H16A . . 109.5 ?
O7 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O7 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C15 O6 H6 . . 110.6 ?
C11 O7 C16 . . 116.75(12) ?
C12 O8 H8 . . 112.1 ?
C18 C17 N4 . . 107.55(15) ?
C18 C17 N6 . . 127.90(15) ?
N4 C17 N6 . . 124.54(14) ?
N5 C18 C17 . . 109.08(15) ?
N5 C18 H18 . . 125.5 ?
C17 C18 H18 . . 125.5 ?
N5 C19 N4 . . 111.28(14) ?
N5 C19 C20 . . 123.58(15) ?
N4 C19 C20 . . 125.14(14) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N4 C21 C22 . . 110.82(13) ?
N4 C21 H21A . . 109.5 ?
C22 C21 H21A . . 109.5 ?
N4 C21 H21B . . 109.5 ?
C22 C21 H21B . . 109.5 ?
H21A C21 H21B . . 108.1 ?
C21 C22 S2 . . 110.80(11) ?
C21 C22 H22A . . 109.5 ?
S2 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
S2 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
C24 C23 S2 . . 108.84(11) ?
C24 C23 H23A . . 109.9 ?
S2 C23 H23A . . 109.9 ?
C24 C23 H23B . . 109.9 ?
S2 C23 H23B . . 109.9 ?
H23A C23 H23B . . 108.3 ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C19 N4 C17 . . 105.48(13) ?
C19 N4 C21 . . 125.99(13) ?
C17 N4 C21 . . 128.48(14) ?
C19 N5 C18 . . 106.61(14) ?
O10 N6 O9 . . 123.71(15) ?
O10 N6 C17 . . 119.87(14) ?
O9 N6 C17 . . 116.42(15) ?
O11 S2 O12 . . 117.34(8) ?
O11 S2 C23 . . 108.82(8) ?
O12 S2 C23 . . 108.23(8) ?
O11 S2 C22 . . 107.58(7) ?
O12 S2 C22 . . 108.17(7) ?
C23 S2 C22 . . 106.16(8) ?
C30 C25 C26 . . 120.32(14) ?
C30 C25 C31 . . 121.99(14) ?
C26 C25 C31 . . 117.65(14) ?
C27 C26 C25 . . 120.07(14) ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
O15 C27 C26 . . 125.13(14) ?
O15 C27 C28 . . 115.31(13) ?
C26 C27 C28 . . 119.52(14) ?
O16 C28 C29 . . 123.28(14) ?
O16 C28 C27 . . 116.85(14) ?
C29 C28 C27 . . 119.85(14) ?
C30 C29 C28 . . 120.78(14) ?
C30 C29 H29 . . 119.6 ?
C28 C29 H29 . . 119.6 ?
C29 C30 C25 . . 119.45(15) ?
C29 C30 H30 . . 120.3 ?
C25 C30 H30 . . 120.3 ?
O14 C31 O13 . . 122.42(15) ?
O14 C31 C25 . . 122.36(15) ?
O13 C31 C25 . . 115.21(14) ?
O15 C32 H32A . . 109.5 ?
O15 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
O15 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 O13 H13A . . 106.3 ?
C27 O15 C32 . . 117.33(12) ?
C28 O16 H16 . . 113.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.361(2) ?
C1 N1 . 1.3865(19) ?
C1 N3 . 1.419(2) ?
C2 N2 . 1.355(2) ?
C2 H2 . 0.9500 ?
C3 N2 . 1.3374(19) ?
C3 N1 . 1.3542(19) ?
C3 C4 . 1.484(2) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 N1 . 1.4719(18) ?
C5 C6 . 1.520(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 S1 . 1.7716(15) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.527(2) ?
C7 S1 . 1.7724(17) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
N3 O2 . 1.2311(18) ?
N3 O1 . 1.2329(17) ?
O3 S1 . 1.4410(12) ?
O4 S1 . 1.4408(13) ?
C9 C14 . 1.389(2) ?
C9 C10 . 1.401(2) ?
C9 C15 . 1.474(2) ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.9500 ?
C11 O7 . 1.3636(18) ?
C11 C12 . 1.412(2) ?
C12 O8 . 1.3555(18) ?
C12 C13 . 1.386(2) ?
C13 C14 . 1.387(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 O5 . 1.2344(19) ?
C15 O6 . 1.3113(19) ?
C16 O7 . 1.4306(18) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
O6 H6 . 0.8811 ?
O8 H8 . 0.8742 ?
C17 C18 . 1.358(2) ?
C17 N4 . 1.386(2) ?
C17 N6 . 1.419(2) ?
C18 N5 . 1.356(2) ?
C18 H18 . 0.9500 ?
C19 N5 . 1.334(2) ?
C19 N4 . 1.355(2) ?
C19 C20 . 1.486(2) ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 N4 . 1.4728(19) ?
C21 C22 . 1.521(2) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 S2 . 1.7850(15) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.524(2) ?
C23 S2 . 1.7671(16) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
N6 O10 . 1.2234(19) ?
N6 O9 . 1.2295(19) ?
O11 S2 . 1.4385(12) ?
O12 S2 . 1.4418(12) ?
C25 C30 . 1.389(2) ?
C25 C26 . 1.406(2) ?
C25 C31 . 1.473(2) ?
C26 C27 . 1.382(2) ?
C26 H26 . 0.9500 ?
C27 O15 . 1.3645(18) ?
C27 C28 . 1.409(2) ?
C28 O16 . 1.3502(18) ?
C28 C29 . 1.388(2) ?
C29 C30 . 1.387(2) ?
C29 H29 . 0.9500 ?
C30 H30 . 0.9500 ?
C31 O14 . 1.225(2) ?
C31 O13 . 1.3217(19) ?
C32 O15 . 1.4235(19) ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
O13 H13A . 0.9048 ?
O16 H16 . 0.8956 ?
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
N1 C1 C2 N2 . . . . 0.99(18) ?
N3 C1 C2 N2 . . . . -179.26(15) ?
N1 C5 C6 S1 . . . . -165.63(10) ?
N2 C3 N1 C1 . . . . 1.63(18) ?
C4 C3 N1 C1 . . . . -176.71(15) ?
N2 C3 N1 C5 . . . . 178.45(13) ?
C4 C3 N1 C5 . . . . 0.1(2) ?
C2 C1 N1 C3 . . . . -1.56(17) ?
N3 C1 N1 C3 . . . . 178.68(15) ?
C2 C1 N1 C5 . . . . -178.21(14) ?
N3 C1 N1 C5 . . . . 2.0(3) ?
C6 C5 N1 C3 . . . . -94.54(17) ?
C6 C5 N1 C1 . . . . 81.51(19) ?
N1 C3 N2 C2 . . . . -1.04(18) ?
C4 C3 N2 C2 . . . . 177.31(16) ?
C1 C2 N2 C3 . . . . 0.00(19) ?
C2 C1 N3 O2 . . . . -174.86(16) ?
N1 C1 N3 O2 . . . . 4.8(2) ?
C2 C1 N3 O1 . . . . 4.8(2) ?
N1 C1 N3 O1 . . . . -175.50(15) ?
C5 C6 S1 O4 . . . . -163.08(11) ?
C5 C6 S1 O3 . . . . -34.38(13) ?
C5 C6 S1 C7 . . . . 81.61(13) ?
C8 C7 S1 O4 . . . . 64.52(16) ?
C8 C7 S1 O3 . . . . -63.80(16) ?
C8 C7 S1 C6 . . . . 179.01(14) ?
C14 C9 C10 C11 . . . . 0.3(2) ?
C15 C9 C10 C11 . . . . 179.54(15) ?
C9 C10 C11 O7 . . . . 177.72(14) ?
C9 C10 C11 C12 . . . . -1.9(2) ?
O7 C11 C12 O8 . . . . 1.2(2) ?
C10 C11 C12 O8 . . . . -179.13(15) ?
O7 C11 C12 C13 . . . . -178.05(14) ?
C10 C11 C12 C13 . . . . 1.6(2) ?
O8 C12 C13 C14 . . . . -178.90(16) ?
C11 C12 C13 C14 . . . . 0.3(3) ?
C12 C13 C14 C9 . . . . -1.9(3) ?
C10 C9 C14 C13 . . . . 1.6(2) ?
C15 C9 C14 C13 . . . . -177.60(15) ?
C14 C9 C15 O5 . . . . 167.39(16) ?
C10 C9 C15 O5 . . . . -11.9(2) ?
C14 C9 C15 O6 . . . . -12.1(2) ?
C10 C9 C15 O6 . . . . 168.64(14) ?
C10 C11 O7 C16 . . . . -2.3(2) ?
C12 C11 O7 C16 . . . . 177.37(14) ?
N4 C17 C18 N5 . . . . 0.1(2) ?
N6 C17 C18 N5 . . . . -178.96(18) ?
N4 C21 C22 S2 . . . . 173.86(11) ?
N5 C19 N4 C17 . . . . 0.1(2) ?
C20 C19 N4 C17 . . . . 179.02(17) ?
N5 C19 N4 C21 . . . . 177.60(15) ?
C20 C19 N4 C21 . . . . -3.5(3) ?
C18 C17 N4 C19 . . . . -0.1(2) ?
N6 C17 N4 C19 . . . . 179.01(17) ?
C18 C17 N4 C21 . . . . -177.57(16) ?
N6 C17 N4 C21 . . . . 1.6(3) ?
C22 C21 N4 C19 . . . . 100.69(18) ?
C22 C21 N4 C17 . . . . -82.4(2) ?
N4 C19 N5 C18 . . . . 0.0(2) ?
C20 C19 N5 C18 . . . . -178.95(17) ?
C17 C18 N5 C19 . . . . -0.1(2) ?
C18 C17 N6 O10 . . . . -174.3(2) ?
N4 C17 N6 O10 . . . . 6.8(3) ?
C18 C17 N6 O9 . . . . 6.1(3) ?
N4 C17 N6 O9 . . . . -172.85(19) ?
C24 C23 S2 O11 . . . . -62.57(15) ?
C24 C23 S2 O12 . . . . 65.97(15) ?
C24 C23 S2 C22 . . . . -178.11(13) ?
C21 C22 S2 O11 . . . . 150.14(11) ?
C21 C22 S2 O12 . . . . 22.48(14) ?
C21 C22 S2 C23 . . . . -93.49(13) ?
C30 C25 C26 C27 . . . . -0.8(2) ?
C31 C25 C26 C27 . . . . 177.05(15) ?
C25 C26 C27 O15 . . . . -176.95(15) ?
C25 C26 C27 C28 . . . . 0.9(2) ?
O15 C27 C28 O16 . . . . -0.3(2) ?
C26 C27 C28 O16 . . . . -178.35(14) ?
O15 C27 C28 C29 . . . . 178.07(14) ?
C26 C27 C28 C29 . . . . 0.0(2) ?
O16 C28 C29 C30 . . . . 177.21(15) ?
C27 C28 C29 C30 . . . . -1.0(2) ?
C28 C29 C30 C25 . . . . 1.1(3) ?
C26 C25 C30 C29 . . . . -0.2(2) ?
C31 C25 C30 C29 . . . . -177.97(16) ?
C30 C25 C31 O14 . . . . 176.00(17) ?
C26 C25 C31 O14 . . . . -1.8(3) ?
C30 C25 C31 O13 . . . . -3.7(2) ?
C26 C25 C31 O13 . . . . 178.44(15) ?
C26 C27 O15 C32 . . . . -3.7(2) ?
C28 C27 O15 C32 . . . . 178.38(14) ?

_cod_database_fobs_code 2022004
