# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tnx_aceton
_database_code_depnum_ccdc_archive 'CCDC 1538111'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'tenoxicam acetone solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O4 S2, C3 H6 O'
_chemical_formula_sum            'C16 H17 N3 O5 S2'
_chemical_formula_weight         395.44
_chemical_melting_point          ?
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'

_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_IT_number           2
_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                   8.9341(4)
_cell_length_b                   8.9659(5)
_cell_length_c                   11.9315(6)
_cell_angle_alpha                75.325(4)
_cell_angle_beta                 81.348(4)
_cell_angle_gamma                89.620(4)
_cell_volume                     913.55(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6678
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3360
_cell_measurement_theta_min      3.8000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         3.295
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -11.00   1.00   15.00    --  -11.43 147.00-108.90   72
  2  ω    -90.00 -18.00   1.00   15.00    --  -11.43 157.00 153.69   72
  3  ω    -90.00 -16.00   1.00   15.00    --  -11.43 156.00 -16.45   74
  4  ω    -58.00  41.00   1.00   15.00    --   11.59 -57.00 150.00   99
  5  ω    -15.00  87.00   1.00   15.00    --   11.59  38.00-150.00  102
  6  ω    -17.00  78.00   1.00   15.00    --   11.59  57.00 -60.00   95
  7  ω    -13.00  90.00   1.00   15.00    --   11.59  77.00  60.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3370
_reflns_number_total             4269
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.052
_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)+(0.0532P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
3.a Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64679(5) 0.55748(5) 0.81132(3) 0.04193(13) Uani 1 1 d . . . . .
S2 S 0.27683(5) 0.45221(6) 0.66354(4) 0.05121(15) Uani 1 1 d . . . . .
O3 O 0.60687(14) 0.68953(15) 0.85451(10) 0.0518(3) Uani 1 1 d . . . . .
O1 O 0.88141(13) 0.87648(14) 0.52662(10) 0.0512(3) Uani 1 1 d . . . . .
O2 O 0.44108(13) 0.74202(15) 0.50341(10) 0.0506(3) Uani 1 1 d . . . . .
N3 N 0.74324(15) 0.61764(15) 0.68037(11) 0.0399(3) Uani 1 1 d . . . . .
N2 N 0.68142(17) 0.92368(16) 0.42450(12) 0.0428(3) Uani 1 1 d . . . . .
H2 H 0.592(2) 0.888(2) 0.4218(17) 0.051 Uiso 1 1 d R . . . .
O4 O 0.72845(15) 0.43924(16) 0.87912(11) 0.0602(4) Uani 1 1 d . . . . .
N1 N 0.88008(16) 1.10430(16) 0.33983(12) 0.0432(3) Uani 1 1 d . . . . .
H1 H 0.925(2) 1.066(2) 0.3994(18) 0.052 Uiso 1 1 d R . . . .
C6 C 0.75133(18) 0.84071(18) 0.51692(14) 0.0395(4) Uani 1 1 d . . . . .
C9 C 0.44093(18) 0.54107(19) 0.67474(14) 0.0393(3) Uani 1 1 d . . . . .
C5 C 0.74400(18) 1.04460(18) 0.33679(13) 0.0386(3) Uani 1 1 d . . . . .
C7 C 0.66255(18) 0.71435(18) 0.59417(13) 0.0380(3) Uani 1 1 d . . . . .
C10 C 0.48391(19) 0.47792(19) 0.78157(14) 0.0412(4) Uani 1 1 d . . . . .
C13 C 0.8429(3) 0.5075(3) 0.63485(19) 0.0587(5) Uani 1 1 d . . . . .
H13A H 0.891(3) 0.445(3) 0.700(2) 0.088 Uiso 1 1 d R . . . .
H13B H 0.915(3) 0.568(3) 0.569(2) 0.088 Uiso 1 1 d R . . . .
H13C H 0.783(3) 0.438(3) 0.605(2) 0.088 Uiso 1 1 d R . . . .
C8 C 0.51527(18) 0.67263(19) 0.58291(13) 0.0388(3) Uani 1 1 d . . . . .
O5 O 0.9728(2) 0.1431(2) 0.7884(2) 0.1103(7) Uani 1 1 d . . . . .
C1 C 0.9503(2) 1.2214(2) 0.25378(17) 0.0514(4) Uani 1 1 d . . . . .
H1A H 1.041(2) 1.245(2) 0.2667(19) 0.062 Uiso 1 1 d R . . . .
C4 C 0.6711(2) 1.1111(2) 0.24150(15) 0.0482(4) Uani 1 1 d . . . . .
H4 H 0.575(2) 1.066(2) 0.2393(18) 0.058 Uiso 1 1 d R . . . .
C11 C 0.3863(2) 0.3577(2) 0.85458(17) 0.0549(5) Uani 1 1 d . . . . .
H11 H 0.394(2) 0.305(3) 0.931(2) 0.066 Uiso 1 1 d R . . . .
C2 C 0.8831(2) 1.2855(2) 0.15983(17) 0.0538(5) Uani 1 1 d . . . . .
H2A H 0.930(2) 1.367(3) 0.103(2) 0.065 Uiso 1 1 d R . . . .
C3 C 0.7409(2) 1.2303(2) 0.15438(16) 0.0514(4) Uani 1 1 d . . . . .
H3 H 0.689(2) 1.275(2) 0.0907(19) 0.062 Uiso 1 1 d R . . . .
C12 C 0.2703(2) 0.3321(2) 0.80033(18) 0.0599(5) Uani 1 1 d . . . . .
H12 H 0.192(3) 0.258(3) 0.824(2) 0.072 Uiso 1 1 d R . . . .
C14 C 0.7546(4) 0.0955(4) 0.7163(3) 0.0891(8) Uani 1 1 d . . . . .
H14A H 0.671(4) 0.168(4) 0.720(3) 0.134 Uiso 1 1 d R . . . .
H14B H 0.712(4) -0.006(4) 0.723(3) 0.134 Uiso 1 1 d R . . . .
H14C H 0.827(4) 0.146(4) 0.637(3) 0.134 Uiso 1 1 d R . . . .
C15 C 0.8457(3) 0.0907(2) 0.8108(2) 0.0697(6) Uani 1 1 d . . . . .
C16 C 0.782(2) 0.001(3) 0.9325(12) 0.111(5) Uani 0.58(6) 1 d . . P A 1
H16A H 0.846597 0.015698 0.986218 0.167 Uiso 0.58(6) 1 calc GR . P A 1
H16B H 0.774258 -0.106326 0.934893 0.167 Uiso 0.58(6) 1 calc GR . P A 1
H16C H 0.682569 0.037111 0.954222 0.167 Uiso 0.58(6) 1 calc GR . P A 1
C16A C 0.760(4) 0.046(3) 0.922(3) 0.199(16) Uani 0.42(6) 1 d . . P A 2
H16D H 0.787943 -0.054437 0.961682 0.298 Uiso 0.42(6) 1 calc GR . P A 2
H16E H 0.654428 0.044520 0.914851 0.298 Uiso 0.42(6) 1 calc GR . P A 2
H16F H 0.778455 0.118810 0.965754 0.298 Uiso 0.42(6) 1 calc GR . P A 2


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4292(13) . ?
S1 N3 1.6275(14) . ?
S1 O4 1.4295(13) . ?
S1 C10 1.7464(16) . ?
S2 C9 1.7118(16) . ?
S2 C12 1.705(2) . ?
O1 C6 1.2373(19) . ?
O2 C8 1.2692(19) . ?
N3 C7 1.4465(19) . ?
N3 C13 1.476(2) . ?
N2 H2 0.87(2) . ?
N2 C6 1.395(2) . ?
N2 C5 1.357(2) . ?
N1 H1 0.86(2) . ?
N1 C5 1.341(2) . ?
N1 C1 1.349(2) . ?
C6 C7 1.423(2) . ?
C9 C10 1.368(2) . ?
C9 C8 1.473(2) . ?
C5 C4 1.395(2) . ?
C7 C8 1.405(2) . ?
C10 C11 1.411(2) . ?
C13 H13A 0.98(3) . ?
C13 H13B 0.98(3) . ?
C13 H13C 0.99(3) . ?
O5 C15 1.198(3) . ?
C1 H1A 0.89(2) . ?
C1 C2 1.349(3) . ?
C4 H4 0.96(2) . ?
C4 C3 1.364(3) . ?
C11 H11 0.92(2) . ?
C11 C12 1.351(3) . ?
C2 H2A 0.91(2) . ?
C2 C3 1.383(3) . ?
C3 H3 0.95(2) . ?
C12 H12 0.93(2) . ?
C14 H14A 0.99(4) . ?
C14 H14B 0.97(4) . ?
C14 H14C 1.07(4) . ?
C14 C15 1.478(4) . ?
C15 C16 1.498(14) . ?
C15 C16A 1.39(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N3 107.92(7) . . ?
O3 S1 O4 118.44(8) . . ?
O3 S1 C10 108.98(8) . . ?
N3 S1 C10 101.43(7) . . ?
O4 S1 N3 108.73(8) . . ?
O4 S1 C10 109.97(8) . . ?
C12 S2 C9 91.66(9) . . ?
C7 N3 S1 115.36(11) . . ?
C7 N3 C13 114.08(14) . . ?
C13 N3 S1 117.73(12) . . ?
C6 N2 H2 115.1(13) . . ?
C5 N2 H2 118.7(13) . . ?
C5 N2 C6 126.11(15) . . ?
C5 N1 H1 118.7(13) . . ?
C5 N1 C1 122.99(15) . . ?
C1 N1 H1 118.3(13) . . ?
O1 C6 N2 120.74(14) . . ?
O1 C6 C7 124.60(14) . . ?
N2 C6 C7 114.65(14) . . ?
C10 C9 S2 110.12(12) . . ?
C10 C9 C8 126.79(15) . . ?
C8 C9 S2 122.98(12) . . ?
N2 C5 C4 122.12(16) . . ?
N1 C5 N2 120.11(14) . . ?
N1 C5 C4 117.76(15) . . ?
C6 C7 N3 114.00(13) . . ?
C8 C7 N3 120.86(13) . . ?
C8 C7 C6 124.77(14) . . ?
C9 C10 S1 116.95(13) . . ?
C9 C10 C11 114.37(16) . . ?
C11 C10 S1 128.66(13) . . ?
N3 C13 H13A 108.5(15) . . ?
N3 C13 H13B 107.2(14) . . ?
N3 C13 H13C 110.0(15) . . ?
H13A C13 H13B 114(2) . . ?
H13A C13 H13C 109(2) . . ?
H13B C13 H13C 108(2) . . ?
O2 C8 C9 118.39(14) . . ?
O2 C8 C7 125.39(15) . . ?
C7 C8 C9 116.17(13) . . ?
N1 C1 H1A 112.5(14) . . ?
N1 C1 C2 120.17(18) . . ?
C2 C1 H1A 127.3(15) . . ?
C5 C4 H4 117.1(12) . . ?
C3 C4 C5 119.65(18) . . ?
C3 C4 H4 123.2(12) . . ?
C10 C11 H11 126.7(14) . . ?
C12 C11 C10 110.62(17) . . ?
C12 C11 H11 122.6(13) . . ?
C1 C2 H2A 119.8(14) . . ?
C1 C2 C3 118.87(17) . . ?
C3 C2 H2A 121.2(14) . . ?
C4 C3 C2 120.52(17) . . ?
C4 C3 H3 118.6(13) . . ?
C2 C3 H3 120.8(12) . . ?
S2 C12 H12 115.8(14) . . ?
C11 C12 S2 113.23(15) . . ?
C11 C12 H12 130.9(14) . . ?
H14A C14 H14B 109(3) . . ?
H14A C14 H14C 105(3) . . ?
H14B C14 H14C 116(3) . . ?
C15 C14 H14A 111(2) . . ?
C15 C14 H14B 110(2) . . ?
C15 C14 H14C 105.7(18) . . ?
O5 C15 C14 120.6(3) . . ?
O5 C15 C16 121.1(6) . . ?
O5 C15 C16A 125.8(13) . . ?
C14 C15 C16 117.9(6) . . ?
C16A C15 C14 112.6(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16A H16D 109.5 . . ?
C15 C16A H16E 109.5 . . ?
C15 C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.87(2) 1.86(2) 2.6098(19) 143.0(18) . yes
N1 H1 O1 0.86(2) 1.97(2) 2.6155(18) 130.9(17) . yes
N1 H1 O1 0.86(2) 2.18(2) 2.8767(18) 138.2(17) 2_776 yes

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N3 C7 C6 139.80(13) . . . . ?
S1 N3 C7 C8 -46.84(19) . . . . ?
S1 C10 C11 C12 178.51(16) . . . . ?
S2 C9 C10 S1 -178.21(9) . . . . ?
S2 C9 C10 C11 0.3(2) . . . . ?
S2 C9 C8 O2 14.0(2) . . . . ?
S2 C9 C8 C7 -168.41(12) . . . . ?
O3 S1 N3 C7 -62.44(13) . . . . ?
O3 S1 N3 C13 158.17(14) . . . . ?
O3 S1 C10 C9 84.28(15) . . . . ?
O3 S1 C10 C11 -94.04(19) . . . . ?
O1 C6 C7 N3 -6.4(2) . . . . ?
O1 C6 C7 C8 -179.47(16) . . . . ?
N3 S1 C10 C9 -29.40(16) . . . . ?
N3 S1 C10 C11 152.28(18) . . . . ?
N3 C7 C8 O2 -173.18(16) . . . . ?
N3 C7 C8 C9 9.4(2) . . . . ?
N2 C6 C7 N3 172.41(14) . . . . ?
N2 C6 C7 C8 -0.7(2) . . . . ?
N2 C5 C4 C3 -178.50(17) . . . . ?
O4 S1 N3 C7 167.91(11) . . . . ?
O4 S1 N3 C13 28.51(16) . . . . ?
O4 S1 C10 C9 -144.36(14) . . . . ?
O4 S1 C10 C11 37.3(2) . . . . ?
N1 C5 C4 C3 1.6(3) . . . . ?
N1 C1 C2 C3 0.8(3) . . . . ?
C6 N2 C5 N1 -6.6(3) . . . . ?
C6 N2 C5 C4 173.52(16) . . . . ?
C6 C7 C8 O2 -0.6(3) . . . . ?
C6 C7 C8 C9 -177.93(16) . . . . ?
C9 S2 C12 C11 0.70(19) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C5 N2 C6 O1 1.7(3) . . . . ?
C5 N2 C6 C7 -177.21(16) . . . . ?
C5 N1 C1 C2 0.9(3) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C10 S1 N3 C7 52.03(13) . . . . ?
C10 S1 N3 C13 -87.37(15) . . . . ?
C10 C9 C8 O2 -161.84(17) . . . . ?
C10 C9 C8 C7 15.7(3) . . . . ?
C10 C11 C12 S2 -0.6(3) . . . . ?
C13 N3 C7 C6 -79.32(19) . . . . ?
C13 N3 C7 C8 94.05(19) . . . . ?
C8 C9 C10 S1 -1.9(3) . . . . ?
C8 C9 C10 C11 176.65(17) . . . . ?
C1 N1 C5 N2 177.99(17) . . . . ?
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C12 S2 C9 C10 -0.58(15) . . . . ?
C12 S2 C9 C8 -177.05(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tnx_chcl3_II
_database_code_depnum_ccdc_archive 'CCDC 1904023'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'tenoxicam chloroform II solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O4 S2, 2(C H Cl3)'
_chemical_formula_sum            'C15 H13 Cl6 N3 O4 S2'
_chemical_formula_weight         576.10
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 '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'
Cl Cl 0.1750 0.1990 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1470 0.1550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5960(19)
_cell_length_b                   16.740(3)
_cell_length_c                   28.301(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4546.2(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      62.03
_cell_measurement_theta_min      3.156
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    1.332
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            38347
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        28.439
_diffrn_reflns_theta_max         31.009
_diffrn_reflns_theta_min         1.873
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       /f
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7937
_diffrn_source                   ?
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                7832
_reflns_number_total             10006
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.216
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     552
_refine_ls_number_reflns         10006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0875P)²+11.7036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C15A(0.5) H15A(0.5) C1(0.5) H1(0.5)
3.a Ternary CH refined with riding coordinates:
 C14B(H14B), C14A(H14A), C15B(H15B), C15A(H15A), C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 N2B(H2B), N2A(H2A), N1B(H1B), N1A(H1A), C4A(H4A), C4B(H4B), C2B(H2BA),
 C11B(H11B), C11A(H11A), C3A(H3A), C3B(H3B), C1B(H1BA), C12B(H12B), C1A(H1AA),
 C2A(H2AA), C12A(H12A)
3.c Idealised Me refined as rotating group:
 C13A(H13D,H13E,H13F), C13B(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1B S 1.0592(2) 0.86244(12) 0.91204(6) 0.0305(4) Uani 1 1 d . . . . .
S1A S 1.4248(2) 0.70239(13) 0.59746(6) 0.0328(5) Uani 1 1 d . . . . .
S2B S 1.4046(2) 0.70885(13) 0.91372(7) 0.0352(5) Uani 1 1 d . . . . .
Cl3B Cl 1.4729(3) 0.58646(14) 0.72999(7) 0.0434(5) Uani 1 1 d . . . . .
Cl2B Cl 1.5351(3) 0.49301(13) 0.81405(8) 0.0429(5) Uani 1 1 d . . . . .
S2A S 1.0592(3) 0.83938(14) 0.60731(7) 0.0363(5) Uani 1 1 d . . . . .
Cl5B Cl 1.1336(3) 0.61259(14) 0.99301(9) 0.0452(6) Uani 1 1 d . . . . .
Cl1B Cl 1.6294(3) 0.65681(13) 0.80670(8) 0.0421(5) Uani 1 1 d . . . . .
Cl4B Cl 1.2008(4) 0.44850(16) 1.01134(10) 0.0588(7) Uani 1 1 d . . . . .
Cl6B Cl 1.2202(3) 0.50990(18) 0.91624(9) 0.0591(7) Uani 1 1 d . . . . .
Cl5A Cl 0.8286(3) 0.47568(18) 1.01159(11) 0.0619(8) Uani 1 1 d . . . . .
Cl3A Cl 1.1872(3) 0.4662(2) 0.78946(11) 0.0679(9) Uani 1 1 d . . . . .
Cl1A Cl 0.9591(4) 0.4680(2) 0.72441(12) 0.0866(13) Uani 1 1 d . . . . .
Cl6A Cl 0.5613(4) 0.3995(3) 1.00345(10) 0.0807(11) Uani 1 1 d . . . . .
Cl4A Cl 0.6350(4) 0.5258(2) 0.93882(10) 0.0737(9) Uani 1 1 d . . . . .
Cl2A Cl 0.9350(4) 0.5404(2) 0.81818(15) 0.0870(12) Uani 1 1 d . . . . .
O3B O 1.1050(7) 0.9291(3) 0.88429(19) 0.0337(13) Uani 1 1 d . . . . .
O2A O 1.2030(7) 0.8371(4) 0.70180(19) 0.0340(13) Uani 1 1 d . . . . .
O1A O 1.6297(6) 0.7914(4) 0.71911(18) 0.0328(13) Uani 1 1 d . . . . .
O1B O 0.8614(7) 0.7756(4) 0.78863(19) 0.0359(14) Uani 1 1 d . . . . .
O4A O 1.5056(7) 0.6956(4) 0.55517(18) 0.0384(14) Uani 1 1 d . . . . .
O4B O 0.9746(7) 0.8773(4) 0.95278(19) 0.0352(13) Uani 1 1 d . . . . .
O3A O 1.3901(7) 0.6314(3) 0.6230(2) 0.0349(14) Uani 1 1 d . . . . .
O2B O 1.2709(7) 0.7027(4) 0.81762(19) 0.0360(13) Uani 1 1 d . . . . .
N2B N 1.0591(8) 0.7127(4) 0.7616(2) 0.0320(15) Uani 1 1 d . . . . .
H2B H 1.147010 0.702248 0.767872 0.038 Uiso 1 1 calc R . . . .
N3A N 1.5035(8) 0.7629(4) 0.6333(2) 0.0306(15) Uani 1 1 d . . . . .
N2A N 1.4262(8) 0.8334(4) 0.7532(2) 0.0302(15) Uani 1 1 d . . . . .
H2A H 1.334901 0.831050 0.750785 0.036 Uiso 1 1 calc R . . . .
N3B N 0.9782(8) 0.8003(4) 0.8772(2) 0.0319(15) Uani 1 1 d . . . . .
N1B N 0.8759(8) 0.7007(4) 0.7069(2) 0.0329(15) Uani 1 1 d . . . . .
H1B H 0.823979 0.728597 0.726546 0.039 Uiso 1 1 calc R . . . .
N1A N 1.6160(8) 0.8627(4) 0.8024(2) 0.0316(15) Uani 1 1 d . . . . .
H1A H 1.669879 0.837497 0.782144 0.038 Uiso 1 1 calc R . . . .
C8A C 1.2835(9) 0.8106(5) 0.6690(3) 0.0295(17) Uani 1 1 d . . . . .
C6A C 1.5020(9) 0.8031(5) 0.7157(2) 0.0277(16) Uani 1 1 d . . . . .
C6B C 0.9843(10) 0.7537(5) 0.7961(3) 0.0343(19) Uani 1 1 d . . . . .
C7A C 1.4218(9) 0.7904(5) 0.6734(3) 0.0298(17) Uani 1 1 d . . . . .
C5A C 1.4781(9) 0.8667(5) 0.7939(3) 0.0290(17) Uani 1 1 d . . . . .
C4A C 1.3923(10) 0.9041(5) 0.8265(3) 0.0332(18) Uani 1 1 d . . . . .
H4A H 1.294344 0.906203 0.821878 0.040 Uiso 1 1 calc R . . . .
C4B C 1.0943(10) 0.6471(5) 0.6869(3) 0.0333(18) Uani 1 1 d . . . . .
H4B H 1.190003 0.638808 0.693938 0.040 Uiso 1 1 calc R . . . .
C2B C 0.8979(10) 0.6321(5) 0.6347(3) 0.0354(19) Uani 1 1 d . . . . .
H2BA H 0.858859 0.611973 0.606245 0.042 Uiso 1 1 calc R . . . .
C8B C 1.1944(9) 0.7373(5) 0.8472(3) 0.0314(18) Uani 1 1 d . . . . .
C10B C 1.2048(10) 0.8057(5) 0.9279(3) 0.0319(18) Uani 1 1 d . . . . .
C10A C 1.2711(10) 0.7525(5) 0.5852(3) 0.0324(18) Uani 1 1 d . . . . .
C9A C 1.2194(10) 0.7992(5) 0.6219(3) 0.0325(18) Uani 1 1 d . . . . .
C11B C 1.2864(10) 0.8097(5) 0.9694(3) 0.0336(19) Uani 1 1 d . . . . .
H11B H 1.266877 0.843063 0.995770 0.040 Uiso 1 1 calc R . . . .
C11A C 1.1823(10) 0.7528(5) 0.5455(3) 0.0350(19) Uani 1 1 d . . . . .
H11A H 1.202738 0.725562 0.516855 0.042 Uiso 1 1 calc R . . . .
C9B C 1.2555(9) 0.7545(5) 0.8949(3) 0.0312(18) Uani 1 1 d . . . . .
C5B C 1.0089(10) 0.6868(5) 0.7185(3) 0.0334(19) Uani 1 1 d . . . . .
C7B C 1.0603(9) 0.7650(5) 0.8396(3) 0.0298(17) Uani 1 1 d . . . . .
C3A C 1.4532(10) 0.9383(5) 0.8661(3) 0.0342(19) Uani 1 1 d . . . . .
H3A H 1.395172 0.964196 0.888630 0.041 Uiso 1 1 calc R . . . .
C3B C 1.0382(10) 0.6196(5) 0.6449(3) 0.0355(19) Uani 1 1 d . . . . .
H3B H 1.095601 0.592112 0.622887 0.043 Uiso 1 1 calc R . . . .
C1B C 0.8169(10) 0.6734(5) 0.6658(3) 0.0351(19) Uani 1 1 d . . . . .
H1BA H 0.721326 0.683060 0.659161 0.042 Uiso 1 1 calc R . . . .
C14B C 1.4963(11) 0.5895(6) 0.7924(3) 0.038(2) Uani 1 1 d . . . . .
H14B H 1.407670 0.608307 0.807319 0.045 Uiso 1 1 calc R . . . .
C12B C 1.3966(10) 0.7590(5) 0.9664(3) 0.037(2) Uani 1 1 d . . . . .
H12B H 1.462690 0.752098 0.991024 0.044 Uiso 1 1 calc R . . . .
C1A C 1.6741(10) 0.8962(5) 0.8411(3) 0.036(2) Uani 1 1 d . . . . .
H1AA H 1.771899 0.892186 0.845745 0.044 Uiso 1 1 calc R . . . .
C2A C 1.5940(10) 0.9362(5) 0.8739(3) 0.036(2) Uani 1 1 d . . . . .
H2AA H 1.634649 0.961050 0.900748 0.043 Uiso 1 1 calc R . . . .
C12A C 1.0647(11) 0.7961(6) 0.5524(3) 0.039(2) Uani 1 1 d . . . . .
H12A H 0.993329 0.801895 0.529358 0.046 Uiso 1 1 calc R . . . .
C13A C 1.5919(10) 0.8269(5) 0.6112(3) 0.036(2) Uani 1 1 d . . . . .
H13D H 1.640236 0.804954 0.583557 0.054 Uiso 1 1 calc GR . . . .
H13E H 1.660596 0.845874 0.634194 0.054 Uiso 1 1 calc GR . . . .
H13F H 1.532514 0.871485 0.601300 0.054 Uiso 1 1 calc GR . . . .
C13B C 0.8821(10) 0.7421(6) 0.9012(3) 0.0371(19) Uani 1 1 d . . . . .
H13A H 0.937076 0.699342 0.915801 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.818259 0.719091 0.877879 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.828364 0.769898 0.925657 0.056 Uiso 1 1 calc GR . . . .
C14A C 1.0083(12) 0.4642(7) 0.7848(4) 0.052(3) Uani 1 1 d . . . . .
H14A H 0.975020 0.412149 0.798033 0.063 Uiso 1 1 calc R . . . .
C15B C 1.2412(11) 0.5328(6) 0.9765(3) 0.041(2) Uani 1 1 d . . . . .
H15B H 1.340502 0.548144 0.982230 0.049 Uiso 1 1 calc R . . . .
C15A C 0.6988(19) 0.4507(11) 0.9718(6) 0.036(4) Uani 0.5 1 d . . P A 2
H15A H 0.740114 0.411090 0.949332 0.043 Uiso 0.5 1 calc R . P A 2
C1 C 0.652(3) 0.4775(15) 0.9989(8) 0.059(6) Uani 0.5 1 d . . P A 1
H1 H 0.610874 0.516447 1.021680 0.071 Uiso 0.5 1 calc R . P A 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1B O3B 1.434(6) . ?
S1B O4B 1.432(6) . ?
S1B N3B 1.630(7) . ?
S1B C10B 1.748(10) . ?
S1A O4A 1.431(6) . ?
S1A O3A 1.430(6) . ?
S1A N3A 1.621(7) . ?
S1A C10A 1.732(9) . ?
S2B C9B 1.707(9) . ?
S2B C12B 1.712(9) . ?
Cl3B C14B 1.781(8) . ?
Cl2B C14B 1.767(10) . ?
S2A C9A 1.728(10) . ?
S2A C12A 1.716(9) . ?
Cl5B C15B 1.752(10) . ?
Cl1B C14B 1.750(11) . ?
Cl4B C15B 1.766(10) . ?
Cl6B C15B 1.759(10) . ?
Cl5A C15A 1.731(18) . ?
Cl5A C1 1.73(3) . ?
Cl3A C14A 1.722(12) . ?
Cl1A C14A 1.774(11) . ?
Cl6A C15A 1.812(19) . ?
Cl6A C1 1.58(2) . ?
Cl4A C15A 1.680(19) . ?
Cl4A C1 1.89(2) . ?
Cl2A C14A 1.736(13) . ?
O2A C8A 1.287(10) . ?
O1A C6A 1.244(10) . ?
O1B C6B 1.253(11) . ?
O2B C8B 1.255(10) . ?
N2B H2B 0.8800 . ?
N2B C6B 1.392(11) . ?
N2B C5B 1.380(10) . ?
N3A C7A 1.454(10) . ?
N3A C13A 1.503(11) . ?
N2A H2A 0.8800 . ?
N2A C6A 1.383(10) . ?
N2A C5A 1.371(9) . ?
N3B C7B 1.452(10) . ?
N3B C13B 1.504(11) . ?
N1B H1B 0.8800 . ?
N1B C5B 1.337(12) . ?
N1B C1B 1.373(10) . ?
N1A H1A 0.8800 . ?
N1A C5A 1.347(11) . ?
N1A C1A 1.350(10) . ?
C8A C7A 1.376(12) . ?
C8A C9A 1.479(10) . ?
C6A C7A 1.438(11) . ?
C6B C7B 1.444(11) . ?
C5A C4A 1.386(11) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.389(11) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.384(12) . ?
C4B C3B 1.385(12) . ?
C2B H2BA 0.9500 . ?
C2B C3B 1.393(14) . ?
C2B C1B 1.362(12) . ?
C8B C9B 1.501(11) . ?
C8B C7B 1.384(12) . ?
C10B C11B 1.415(11) . ?
C10B C9B 1.357(12) . ?
C10A C9A 1.392(11) . ?
C10A C11A 1.411(11) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.358(13) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.355(13) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.369(14) . ?
C3B H3B 0.9500 . ?
C1B H1BA 0.9500 . ?
C14B H14B 1.0000 . ?
C12B H12B 0.9500 . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.379(12) . ?
C2A H2AA 0.9500 . ?
C12A H12A 0.9500 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C13B H13A 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C14A H14A 1.0000 . ?
C15B H15B 1.0000 . ?
C15A H15A 1.0000 . ?
C1 H1 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3B S1B N3B 108.2(3) . . ?
O3B S1B C10B 108.6(4) . . ?
O4B S1B O3B 118.7(4) . . ?
O4B S1B N3B 109.1(4) . . ?
O4B S1B C10B 110.0(4) . . ?
N3B S1B C10B 100.9(4) . . ?
O4A S1A N3A 108.7(4) . . ?
O4A S1A C10A 109.4(4) . . ?
O3A S1A O4A 118.8(4) . . ?
O3A S1A N3A 108.2(4) . . ?
O3A S1A C10A 107.8(4) . . ?
N3A S1A C10A 102.7(4) . . ?
C9B S2B C12B 90.8(4) . . ?
C12A S2A C9A 91.5(4) . . ?
C6B N2B H2B 116.8 . . ?
C5B N2B H2B 116.8 . . ?
C5B N2B C6B 126.4(8) . . ?
C7A N3A S1A 115.8(6) . . ?
C7A N3A C13A 113.9(7) . . ?
C13A N3A S1A 116.5(5) . . ?
C6A N2A H2A 116.5 . . ?
C5A N2A H2A 116.5 . . ?
C5A N2A C6A 127.0(8) . . ?
C7B N3B S1B 116.4(6) . . ?
C7B N3B C13B 113.6(7) . . ?
C13B N3B S1B 115.7(5) . . ?
C5B N1B H1B 118.5 . . ?
C5B N1B C1B 122.9(8) . . ?
C1B N1B H1B 118.5 . . ?
C5A N1A H1A 119.0 . . ?
C5A N1A C1A 122.0(8) . . ?
C1A N1A H1A 119.0 . . ?
O2A C8A C7A 126.7(7) . . ?
O2A C8A C9A 116.4(8) . . ?
C7A C8A C9A 116.8(7) . . ?
O1A C6A N2A 121.0(7) . . ?
O1A C6A C7A 124.6(7) . . ?
N2A C6A C7A 114.3(7) . . ?
O1B C6B N2B 120.8(7) . . ?
O1B C6B C7B 125.5(8) . . ?
N2B C6B C7B 113.7(8) . . ?
C8A C7A N3A 121.8(7) . . ?
C8A C7A C6A 123.8(7) . . ?
C6A C7A N3A 114.1(7) . . ?
N2A C5A C4A 121.8(8) . . ?
N1A C5A N2A 119.1(7) . . ?
N1A C5A C4A 119.1(7) . . ?
C5A C4A H4A 120.8 . . ?
C5A C4A C3A 118.4(9) . . ?
C3A C4A H4A 120.8 . . ?
C5B C4B H4B 120.5 . . ?
C3B C4B H4B 120.5 . . ?
C3B C4B C5B 119.0(9) . . ?
C3B C2B H2BA 120.2 . . ?
C1B C2B H2BA 120.2 . . ?
C1B C2B C3B 119.6(8) . . ?
O2B C8B C9B 117.4(8) . . ?
O2B C8B C7B 126.5(8) . . ?
C7B C8B C9B 116.0(7) . . ?
C11B C10B S1B 129.0(7) . . ?
C9B C10B S1B 117.0(6) . . ?
C9B C10B C11B 113.8(8) . . ?
C9A C10A S1A 115.2(6) . . ?
C9A C10A C11A 112.2(8) . . ?
C11A C10A S1A 132.6(7) . . ?
C8A C9A S2A 122.3(6) . . ?
C10A C9A S2A 110.9(6) . . ?
C10A C9A C8A 126.7(8) . . ?
C10B C11B H11B 124.8 . . ?
C12B C11B C10B 110.4(8) . . ?
C12B C11B H11B 124.8 . . ?
C10A C11A H11A 123.5 . . ?
C12A C11A C10A 113.0(7) . . ?
C12A C11A H11A 123.5 . . ?
C8B C9B S2B 121.5(6) . . ?
C10B C9B S2B 111.6(6) . . ?
C10B C9B C8B 126.9(8) . . ?
N2B C5B C4B 121.0(8) . . ?
N1B C5B N2B 119.7(8) . . ?
N1B C5B C4B 119.3(8) . . ?
C6B C7B N3B 113.9(7) . . ?
C8B C7B N3B 121.8(7) . . ?
C8B C7B C6B 123.9(7) . . ?
C4A C3A H3A 118.9 . . ?
C2A C3A C4A 122.3(8) . . ?
C2A C3A H3A 118.9 . . ?
C4B C3B C2B 120.2(8) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
N1B C1B H1BA 120.6 . . ?
C2B C1B N1B 118.8(9) . . ?
C2B C1B H1BA 120.6 . . ?
Cl3B C14B H14B 108.7 . . ?
Cl2B C14B Cl3B 110.1(5) . . ?
Cl2B C14B H14B 108.7 . . ?
Cl1B C14B Cl3B 109.8(5) . . ?
Cl1B C14B Cl2B 110.8(5) . . ?
Cl1B C14B H14B 108.7 . . ?
S2B C12B H12B 123.3 . . ?
C11B C12B S2B 113.4(6) . . ?
C11B C12B H12B 123.3 . . ?
N1A C1A H1AA 119.4 . . ?
N1A C1A C2A 121.1(9) . . ?
C2A C1A H1AA 119.4 . . ?
C3A C2A C1A 117.0(8) . . ?
C3A C2A H2AA 121.5 . . ?
C1A C2A H2AA 121.5 . . ?
S2A C12A H12A 123.8 . . ?
C11A C12A S2A 112.4(6) . . ?
C11A C12A H12A 123.8 . . ?
N3A C13A H13D 109.5 . . ?
N3A C13A H13E 109.5 . . ?
N3A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
N3B C13B H13A 109.5 . . ?
N3B C13B H13B 109.5 . . ?
N3B C13B H13C 109.5 . . ?
H13A C13B H13B 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
Cl3A C14A Cl1A 109.7(6) . . ?
Cl3A C14A Cl2A 110.3(6) . . ?
Cl3A C14A H14A 107.9 . . ?
Cl1A C14A H14A 107.9 . . ?
Cl2A C14A Cl1A 112.9(7) . . ?
Cl2A C14A H14A 107.9 . . ?
Cl5B C15B Cl4B 109.3(5) . . ?
Cl5B C15B Cl6B 111.0(6) . . ?
Cl5B C15B H15B 108.9 . . ?
Cl4B C15B H15B 108.9 . . ?
Cl6B C15B Cl4B 110.0(5) . . ?
Cl6B C15B H15B 108.9 . . ?
Cl5A C15A Cl6A 108.4(10) . . ?
Cl5A C15A H15A 106.8 . . ?
Cl6A C15A H15A 106.8 . . ?
Cl4A C15A Cl5A 116.3(11) . . ?
Cl4A C15A Cl6A 111.3(10) . . ?
Cl4A C15A H15A 106.8 . . ?
Cl5A C1 Cl4A 106.3(12) . . ?
Cl5A C1 H1 105.5 . . ?
Cl6A C1 Cl5A 120.7(17) . . ?
Cl6A C1 Cl4A 112.3(13) . . ?
Cl6A C1 H1 105.5 . . ?
Cl4A C1 H1 105.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2B H2B O2B 0.88 1.84 2.584(9) 140.6 . yes
N2A H2A O2A 0.88 1.88 2.591(9) 136.6 . yes
N1B H1B O1A 0.88 2.15 2.830(10) 133.5 1_455 yes
N1B H1B O1B 0.88 1.96 2.634(8) 132.5 . yes
N1A H1A O1A 0.88 1.98 2.645(8) 131.2 . yes
N1A H1A O1B 0.88 2.12 2.797(10) 133.5 1_655 yes
C14B H14B O2B 1.00 2.07 2.963(11) 146.8 . yes
C14A H14A O2A 1.00 2.12 2.962(12) 140.7 3_746 yes

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1B N3B C7B C6B -143.7(6) . . . . ?
S1B N3B C7B C8B 42.9(10) . . . . ?
S1B C10B C11B C12B -175.5(7) . . . . ?
S1B C10B C9B S2B 175.5(5) . . . . ?
S1B C10B C9B C8B -4.4(12) . . . . ?
S1A N3A C7A C8A -40.5(10) . . . . ?
S1A N3A C7A C6A 146.4(6) . . . . ?
S1A C10A C9A S2A -175.1(5) . . . . ?
S1A C10A C9A C8A 1.1(12) . . . . ?
S1A C10A C11A C12A 174.6(8) . . . . ?
O3B S1B N3B C7B 62.7(7) . . . . ?
O3B S1B N3B C13B -160.0(6) . . . . ?
O3B S1B C10B C11B 93.8(8) . . . . ?
O3B S1B C10B C9B -80.5(7) . . . . ?
O2A C8A C7A N3A -178.4(8) . . . . ?
O2A C8A C7A C6A -6.0(14) . . . . ?
O2A C8A C9A S2A 14.4(11) . . . . ?
O2A C8A C9A C10A -161.4(8) . . . . ?
O1A C6A C7A N3A -0.7(12) . . . . ?
O1A C6A C7A C8A -173.7(8) . . . . ?
O1B C6B C7B N3B 4.2(13) . . . . ?
O1B C6B C7B C8B 177.4(9) . . . . ?
O4A S1A N3A C7A 167.0(6) . . . . ?
O4A S1A N3A C13A 28.9(7) . . . . ?
O4A S1A C10A C9A -147.7(7) . . . . ?
O4A S1A C10A C11A 35.7(10) . . . . ?
O4B S1B N3B C7B -166.9(6) . . . . ?
O4B S1B N3B C13B -29.7(7) . . . . ?
O4B S1B C10B C11B -37.6(9) . . . . ?
O4B S1B C10B C9B 148.2(7) . . . . ?
O3A S1A N3A C7A -62.7(7) . . . . ?
O3A S1A N3A C13A 159.2(6) . . . . ?
O3A S1A C10A C9A 81.8(7) . . . . ?
O3A S1A C10A C11A -94.8(9) . . . . ?
O2B C8B C9B S2B -15.6(11) . . . . ?
O2B C8B C9B C10B 164.3(9) . . . . ?
O2B C8B C7B N3B 176.5(8) . . . . ?
O2B C8B C7B C6B 3.8(14) . . . . ?
N2B C6B C7B N3B -174.0(7) . . . . ?
N2B C6B C7B C8B -0.7(13) . . . . ?
N3A S1A C10A C9A -32.3(7) . . . . ?
N3A S1A C10A C11A 151.1(9) . . . . ?
N2A C6A C7A N3A 176.7(7) . . . . ?
N2A C6A C7A C8A 3.7(12) . . . . ?
N2A C5A C4A C3A -178.2(8) . . . . ?
N3B S1B C10B C11B -152.6(8) . . . . ?
N3B S1B C10B C9B 33.1(8) . . . . ?
N1A C5A C4A C3A 2.0(12) . . . . ?
N1A C1A C2A C3A 1.7(14) . . . . ?
C6A N2A C5A N1A -8.4(13) . . . . ?
C6A N2A C5A C4A 171.8(8) . . . . ?
C6B N2B C5B N1B -0.2(14) . . . . ?
C6B N2B C5B C4B 179.4(8) . . . . ?
C7A C8A C9A S2A -166.9(7) . . . . ?
C7A C8A C9A C10A 17.3(13) . . . . ?
C5A N2A C6A O1A 12.2(13) . . . . ?
C5A N2A C6A C7A -165.3(8) . . . . ?
C5A N1A C1A C2A 0.2(13) . . . . ?
C5A C4A C3A C2A -0.1(14) . . . . ?
C4A C3A C2A C1A -1.7(14) . . . . ?
C10B S1B N3B C7B -51.2(6) . . . . ?
C10B S1B N3B C13B 86.1(7) . . . . ?
C10B C11B C12B S2B 1.4(10) . . . . ?
C10A S1A N3A C7A 51.1(7) . . . . ?
C10A S1A N3A C13A -87.0(7) . . . . ?
C10A C11A C12A S2A 0.9(11) . . . . ?
C9A S2A C12A C11A 0.3(8) . . . . ?
C9A C8A C7A N3A 3.1(12) . . . . ?
C9A C8A C7A C6A 175.5(8) . . . . ?
C9A C10A C11A C12A -2.0(12) . . . . ?
C11B C10B C9B S2B 0.4(10) . . . . ?
C11B C10B C9B C8B -179.5(8) . . . . ?
C11A C10A C9A S2A 2.2(10) . . . . ?
C11A C10A C9A C8A 178.4(8) . . . . ?
C9B S2B C12B C11B -1.0(7) . . . . ?
C9B C8B C7B N3B -6.9(12) . . . . ?
C9B C8B C7B C6B -179.6(8) . . . . ?
C9B C10B C11B C12B -1.1(11) . . . . ?
C5B N2B C6B O1B -4.8(14) . . . . ?
C5B N2B C6B C7B 173.4(8) . . . . ?
C5B N1B C1B C2B -1.8(13) . . . . ?
C5B C4B C3B C2B 0.2(13) . . . . ?
C7B C8B C9B S2B 167.5(7) . . . . ?
C7B C8B C9B C10B -12.7(13) . . . . ?
C3B C4B C5B N2B 177.6(8) . . . . ?
C3B C4B C5B N1B -2.8(13) . . . . ?
C3B C2B C1B N1B -0.9(14) . . . . ?
C1B N1B C5B N2B -176.7(8) . . . . ?
C1B N1B C5B C4B 3.7(13) . . . . ?
C1B C2B C3B C4B 1.7(14) . . . . ?
C12B S2B C9B C8B -179.8(7) . . . . ?
C12B S2B C9B C10B 0.4(7) . . . . ?
C1A N1A C5A N2A 178.1(8) . . . . ?
C1A N1A C5A C4A -2.1(13) . . . . ?
C12A S2A C9A C8A -177.8(8) . . . . ?
C12A S2A C9A C10A -1.4(7) . . . . ?
C13A N3A C7A C8A 98.7(9) . . . . ?
C13A N3A C7A C6A -74.4(9) . . . . ?
C13B N3B C7B C6B 78.2(9) . . . . ?
C13B N3B C7B C8B -95.2(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform under -18 ?'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tnx_acetonitrile
_database_code_depnum_ccdc_archive 'CCDC 1904101'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'tenoxicam acetonitrile solvat'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O4 S2, C2 H3 N'
_chemical_formula_sum            'C15 H14 N4 O4 S2'
_chemical_formula_weight         378.42
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                   9.1718(3)
_cell_length_b                   8.9965(3)
_cell_length_c                   21.1092(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.591(4)
_cell_angle_gamma                90
_cell_volume                     1722.26(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6671
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1550
_cell_measurement_theta_min      3.7050
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.190
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00   2.00   1.00   90.00    --  -11.27 127.00-122.49   72
  2  ω    -74.00  -2.00   1.00   90.00    --  -11.27 133.00 -23.53   72
  3  ω    -67.00  -5.00   1.00   90.00    --  -11.27 122.00  98.73   62
  4  ω    -90.00 -28.00   1.00   90.00    --  -11.27 -77.00-150.00   62
  5  ω    -85.00  16.00   1.00   90.00    --  -11.27 -57.00  90.00  101
  6  ω    -87.00  13.00   1.00   90.00    --  -11.27 -38.00-120.00  100
  7  ω    -74.00  48.00   1.00   90.00    --  -11.27   0.00 -60.00  122
  8  ω    -77.00 -45.00   1.00   90.00    --   11.43 178.00-150.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0755395000
_diffrn_orient_matrix_UB_12      0.0150364000
_diffrn_orient_matrix_UB_13      -0.0010261000
_diffrn_orient_matrix_UB_21      0.0114499000
_diffrn_orient_matrix_UB_22      0.0127030000
_diffrn_orient_matrix_UB_23      0.0335194000
_diffrn_orient_matrix_UB_31      0.0168119000
_diffrn_orient_matrix_UB_32      -0.0763684000
_diffrn_orient_matrix_UB_33      0.0053893000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2809
_reflns_number_total             3527
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.5668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C2(H2A), C1(H1A), C11(H11), C3(H3), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26080(6) 0.15844(6) 0.66918(2) 0.03739(16) Uani 1 1 d . . . . .
S2 S -0.15771(6) 0.00952(7) 0.58450(3) 0.04344(17) Uani 1 1 d . . . . .
O2 O -0.05353(15) 0.25012(17) 0.49995(7) 0.0444(4) Uani 1 1 d . . . . .
O1 O 0.38693(16) 0.39632(18) 0.51737(7) 0.0483(4) Uani 1 1 d . . . . .
O3 O 0.23540(17) 0.30263(18) 0.69419(7) 0.0494(4) Uani 1 1 d . . . . .
O4 O 0.36648(17) 0.0632(2) 0.70598(8) 0.0569(5) Uani 1 1 d . . . . .
N1 N 0.31803(18) 0.56170(18) 0.41385(8) 0.0350(4) Uani 1 1 d . . . . .
H1 H 0.382351 0.545439 0.447148 0.042 Uiso 1 1 calc R . . . .
N3 N 0.30769(18) 0.18048(19) 0.59807(8) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.15581(19) 0.4041(2) 0.45818(8) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.066367 0.373544 0.456137 0.047 Uiso 1 1 calc R . . . .
C5 C 0.1854(2) 0.4966(2) 0.41028(9) 0.0334(5) Uani 1 1 d . . . . .
C7 C 0.1965(2) 0.2504(2) 0.55090(9) 0.0325(5) Uani 1 1 d . . . . .
C8 C 0.0479(2) 0.2057(2) 0.54358(9) 0.0328(5) Uani 1 1 d . . . . .
C6 C 0.2562(2) 0.3543(2) 0.50995(10) 0.0353(5) Uani 1 1 d . . . . .
C10 C 0.0912(2) 0.0671(2) 0.65065(10) 0.0354(5) Uani 1 1 d . . . . .
C9 C 0.0078(2) 0.1019(2) 0.59272(10) 0.0327(5) Uani 1 1 d . . . . .
C4 C 0.0817(2) 0.5250(3) 0.35618(11) 0.0440(6) Uani 1 1 d . . . . .
H4 H -0.011260 0.481679 0.352329 0.053 Uiso 1 1 calc R . . . .
C2 C 0.2558(2) 0.6813(3) 0.31455(10) 0.0418(5) Uani 1 1 d . . . . .
H2A H 0.280208 0.743811 0.282656 0.050 Uiso 1 1 calc R . . . .
C1 C 0.3552(2) 0.6516(2) 0.36755(10) 0.0397(5) Uani 1 1 d . . . . .
H1A H 0.448899 0.693361 0.371932 0.048 Uiso 1 1 calc R . . . .
C11 C 0.0231(3) -0.0351(3) 0.68807(11) 0.0479(6) Uani 1 1 d . . . . .
H11 H 0.065247 -0.069965 0.728114 0.057 Uiso 1 1 calc R . . . .
C3 C 0.1164(3) 0.6161(3) 0.30895(11) 0.0465(6) Uani 1 1 d . . . . .
H3 H 0.047032 0.634738 0.272985 0.056 Uiso 1 1 calc R . . . .
C13 C 0.3864(3) 0.0557(3) 0.57243(12) 0.0518(6) Uani 1 1 d . . . . .
H13A H 0.463946 0.021483 0.604759 0.078 Uiso 1 1 calc GR . . . .
H13B H 0.427731 0.088782 0.535696 0.078 Uiso 1 1 calc GR . . . .
H13C H 0.318489 -0.024091 0.560205 0.078 Uiso 1 1 calc GR . . . .
C12 C -0.1124(3) -0.0752(3) 0.65747(12) 0.0528(6) Uani 1 1 d . . . . .
H12 H -0.173970 -0.141691 0.674400 0.063 Uiso 1 1 calc R . . . .
C14 C 0.5451(3) 0.3041(3) 0.35379(14) 0.0570(7) Uani 1 1 d . . . . .
N4 N 0.4237(3) 0.2770(3) 0.34459(15) 0.0906(9) Uani 1 1 d . . . . .
C15 C 0.7008(3) 0.3389(3) 0.36419(16) 0.0741(9) Uani 1 1 d . . . . .
H15A H 0.749285 0.284238 0.334309 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.742395 0.312048 0.407115 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.713980 0.443491 0.358068 0.111 Uiso 1 1 calc GR . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4327(17) . ?
S1 O4 1.4324(16) . ?
S1 N3 1.6341(18) . ?
S1 C10 1.751(2) . ?
S2 C9 1.717(2) . ?
S2 C12 1.713(3) . ?
O2 C8 1.272(2) . ?
O1 C6 1.244(2) . ?
N1 H1 0.8600 . ?
N1 C5 1.342(3) . ?
N1 C1 1.351(3) . ?
N3 C7 1.457(2) . ?
N3 C13 1.480(3) . ?
N2 H2 0.8600 . ?
N2 C5 1.368(3) . ?
N2 C6 1.394(3) . ?
C5 C4 1.396(3) . ?
C7 C8 1.408(3) . ?
C7 C6 1.436(3) . ?
C8 C9 1.482(3) . ?
C10 C9 1.378(3) . ?
C10 C11 1.416(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.364(3) . ?
C2 H2A 0.9300 . ?
C2 C1 1.360(3) . ?
C2 C3 1.396(3) . ?
C1 H1A 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.361(3) . ?
C3 H3 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12 0.9300 . ?
C14 N4 1.129(3) . ?
C14 C15 1.446(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N3 107.96(9) . . ?
O3 S1 C10 108.62(10) . . ?
O4 S1 O3 118.41(10) . . ?
O4 S1 N3 108.73(10) . . ?
O4 S1 C10 110.31(10) . . ?
N3 S1 C10 101.46(9) . . ?
C12 S2 C9 91.86(11) . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 123.03(17) . . ?
C1 N1 H1 118.5 . . ?
C7 N3 S1 115.27(14) . . ?
C7 N3 C13 114.01(17) . . ?
C13 N3 S1 116.97(14) . . ?
C5 N2 H2 116.8 . . ?
C5 N2 C6 126.46(17) . . ?
C6 N2 H2 116.8 . . ?
N1 C5 N2 120.16(17) . . ?
N1 C5 C4 117.84(18) . . ?
N2 C5 C4 122.00(19) . . ?
C8 C7 N3 121.27(17) . . ?
C8 C7 C6 124.74(18) . . ?
C6 C7 N3 113.69(17) . . ?
O2 C8 C7 125.54(19) . . ?
O2 C8 C9 118.27(18) . . ?
C7 C8 C9 116.15(17) . . ?
O1 C6 N2 120.84(19) . . ?
O1 C6 C7 124.64(18) . . ?
N2 C6 C7 114.48(18) . . ?
C9 C10 S1 116.63(15) . . ?
C9 C10 C11 114.20(19) . . ?
C11 C10 S1 129.11(16) . . ?
C8 C9 S2 122.86(15) . . ?
C10 C9 S2 110.16(15) . . ?
C10 C9 C8 126.97(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C1 C2 H2A 120.7 . . ?
C1 C2 C3 118.7(2) . . ?
C3 C2 H2A 120.7 . . ?
N1 C1 C2 120.2(2) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C10 C11 H11 124.6 . . ?
C12 C11 C10 110.8(2) . . ?
C12 C11 H11 124.6 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C12 H12 123.5 . . ?
C11 C12 S2 112.98(18) . . ?
C11 C12 H12 123.5 . . ?
N4 C14 C15 178.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.86 2.00 2.641(2) 131.1 . yes
N1 H1 O1 0.86 2.20 2.898(2) 138.2 3_666 yes
N2 H2 O2 0.86 1.90 2.624(2) 141.3 . yes

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N3 C7 C8 -45.8(2) . . . . ?
S1 N3 C7 C6 140.23(16) . . . . ?
S1 C10 C9 S2 -176.98(11) . . . . ?
S1 C10 C9 C8 1.7(3) . . . . ?
S1 C10 C11 C12 177.01(19) . . . . ?
O2 C8 C9 S2 14.0(3) . . . . ?
O2 C8 C9 C10 -164.5(2) . . . . ?
O3 S1 N3 C7 -61.83(16) . . . . ?
O3 S1 N3 C13 160.00(16) . . . . ?
O3 S1 C10 C9 81.77(18) . . . . ?
O3 S1 C10 C11 -95.5(2) . . . . ?
O4 S1 N3 C7 168.53(14) . . . . ?
O4 S1 N3 C13 30.36(18) . . . . ?
O4 S1 C10 C9 -146.94(17) . . . . ?
O4 S1 C10 C11 35.8(2) . . . . ?
N1 C5 C4 C3 0.1(3) . . . . ?
N3 S1 C10 C9 -31.82(19) . . . . ?
N3 S1 C10 C11 150.9(2) . . . . ?
N3 C7 C8 O2 -172.98(19) . . . . ?
N3 C7 C8 C9 9.2(3) . . . . ?
N3 C7 C6 O1 -8.0(3) . . . . ?
N3 C7 C6 N2 170.09(18) . . . . ?
N2 C5 C4 C3 -178.9(2) . . . . ?
C5 N1 C1 C2 0.8(3) . . . . ?
C5 N2 C6 O1 1.9(3) . . . . ?
C5 N2 C6 C7 -176.30(19) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C7 C8 C9 S2 -168.03(16) . . . . ?
C7 C8 C9 C10 13.4(3) . . . . ?
C8 C7 C6 O1 178.3(2) . . . . ?
C8 C7 C6 N2 -3.7(3) . . . . ?
C6 N2 C5 N1 -7.3(3) . . . . ?
C6 N2 C5 C4 171.7(2) . . . . ?
C6 C7 C8 O2 0.3(3) . . . . ?
C6 C7 C8 C9 -177.50(19) . . . . ?
C10 S1 N3 C7 52.26(16) . . . . ?
C10 S1 N3 C13 -85.91(17) . . . . ?
C10 C11 C12 S2 -0.2(3) . . . . ?
C9 S2 C12 C11 0.5(2) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C1 N1 C5 N2 178.57(19) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C11 C10 C9 S2 0.7(2) . . . . ?
C11 C10 C9 C8 179.4(2) . . . . ?
C3 C2 C1 N1 -0.6(3) . . . . ?
C13 N3 C7 C8 93.6(2) . . . . ?
C13 N3 C7 C6 -80.4(2) . . . . ?
C12 S2 C9 C8 -179.44(19) . . . . ?
C12 S2 C9 C10 -0.69(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.910
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tnx_dmfa
_database_code_depnum_ccdc_archive 'CCDC 1538134'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'tenoxicam dimethylformamide solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O4 S2, C3 H7 N O'
_chemical_formula_sum            'C16 H18 N4 O5 S2'
_chemical_formula_weight         410.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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_IT_number           2
_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                   9.1060(4)
_cell_length_b                   9.4381(4)
_cell_length_c                   11.6586(6)
_cell_angle_alpha                74.530(4)
_cell_angle_beta                 77.500(4)
_cell_angle_gamma                85.545(3)
_cell_volume                     942.56(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1190
_cell_measurement_theta_min      1.8380
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.144
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         1.851
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  22.00   1.00   50.00    --  -23.36 -57.00  30.00   62
  2  ω    -43.00  68.00   1.00   50.00    --  -23.36  37.00-120.00  111
  3  ω    -31.00  28.00   1.00   50.00    --   22.89  96.00 -51.00   59
  4  ω     73.00 112.00   1.00   50.00    --   22.89-178.00 -90.00   39
  5  ω    -44.00  76.00   1.00   50.00    --  -23.36  77.00  60.00  120
  6  ω    -80.00  29.00   1.00   50.00    --  -23.36 -37.00 120.00  109
  7  ω    -77.00  29.00   1.00   50.00    --  -23.36  96.00 -51.00  106
  8  ω   -122.00 -84.00   1.00   50.00    --  -23.36 -37.00 120.00   38
  9  ω   -127.00   5.00   1.00   50.00    --  -23.36 -57.00 -30.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0534944000
_diffrn_orient_matrix_UB_12      -0.0562865000
_diffrn_orient_matrix_UB_13      0.0167089000
_diffrn_orient_matrix_UB_21      -0.0111266000
_diffrn_orient_matrix_UB_22      0.0139338000
_diffrn_orient_matrix_UB_23      0.0581610000
_diffrn_orient_matrix_UB_31      -0.0581645000
_diffrn_orient_matrix_UB_32      -0.0521634000
_diffrn_orient_matrix_UB_33      0.0222609000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2958
_reflns_number_total             3857
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+0.1452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H16A)=Sof(O5A)=1-FVAR(1)
 Sof(H16)=Sof(O5B)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C4(H4), C3(H3), C11(H11), C1(H1A), C2(H2A), C12(H12),
 C16(H16), C16(H16A)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35865(6) 0.92496(6) 0.18845(4) 0.04924(17) Uani 1 1 d . . . . .
S2 S 0.69544(7) 1.00371(7) 0.35625(5) 0.0622(2) Uani 1 1 d . . . . .
O3 O 0.41329(17) 0.80319(17) 0.13895(13) 0.0581(4) Uani 1 1 d . . . . .
O1 O 0.11404(17) 0.61233(16) 0.47383(13) 0.0601(4) Uani 1 1 d . . . . .
O2 O 0.53585(17) 0.72437(17) 0.50832(13) 0.0583(4) Uani 1 1 d . . . . .
O4 O 0.27804(18) 1.04101(18) 0.11992(14) 0.0672(5) Uani 1 1 d . . . . .
N3 N 0.25239(18) 0.86108(18) 0.32157(14) 0.0456(4) Uani 1 1 d . . . . .
N2 N 0.30084(19) 0.55867(19) 0.58290(15) 0.0523(4) Uani 1 1 d . . . . .
H2 H 0.389447 0.581561 0.585481 0.063 Uiso 1 1 calc R . . . .
N1 N 0.1038(2) 0.39472(19) 0.66938(15) 0.0524(4) Uani 1 1 d . . . . .
H1 H 0.063598 0.434906 0.607865 0.063 Uiso 1 1 calc R . . . .
C5 C 0.2360(2) 0.4440(2) 0.67318(18) 0.0479(5) Uani 1 1 d . . . . .
C9 C 0.5423(2) 0.9260(2) 0.33681(18) 0.0481(5) Uani 1 1 d . . . . .
C7 C 0.3270(2) 0.7633(2) 0.41123(17) 0.0451(5) Uani 1 1 d . . . . .
C6 C 0.2389(2) 0.6424(2) 0.48718(18) 0.0478(5) Uani 1 1 d . . . . .
C8 C 0.4672(2) 0.7973(2) 0.42670(17) 0.0468(5) Uani 1 1 d . . . . .
C10 C 0.5073(2) 0.9950(2) 0.22682(18) 0.0484(5) Uani 1 1 d . . . . .
N4 N 0.7999(3) 0.5891(2) 0.8162(3) 0.0779(6) Uani 1 1 d . . . . .
C4 C 0.3025(3) 0.3762(2) 0.7712(2) 0.0570(6) Uani 1 1 d . . . . .
H4 H 0.395329 0.406757 0.775525 0.068 Uiso 1 1 calc R . . . .
C3 C 0.2303(3) 0.2643(3) 0.8610(2) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.274589 0.218331 0.926539 0.076 Uiso 1 1 calc R . . . .
C11 C 0.6035(3) 1.1119(3) 0.1577(2) 0.0603(6) Uani 1 1 d . . . . .
H11 H 0.595284 1.169419 0.080913 0.072 Uiso 1 1 calc R . . . .
C1 C 0.0306(3) 0.2845(2) 0.7579(2) 0.0603(6) Uani 1 1 d . . . . .
H1A H -0.061518 0.254025 0.751852 0.072 Uiso 1 1 calc R . . . .
C2 C 0.0918(3) 0.2187(3) 0.8553(2) 0.0661(7) Uani 1 1 d . . . . .
H2A H 0.041570 0.144090 0.917481 0.079 Uiso 1 1 calc R . . . .
C13 C 0.1400(3) 0.9623(3) 0.3699(2) 0.0651(6) Uani 1 1 d . . . . .
H13A H 0.189360 1.029916 0.396928 0.098 Uiso 1 1 calc GR . . . .
H13B H 0.068623 0.907079 0.437124 0.098 Uiso 1 1 calc GR . . . .
H13C H 0.088571 1.015897 0.307363 0.098 Uiso 1 1 calc GR . . . .
C12 C 0.7093(3) 1.1285(3) 0.2188(2) 0.0683(7) Uani 1 1 d . . . . .
H12 H 0.781847 1.200549 0.188695 0.082 Uiso 1 1 calc R . . . .
C15 C 0.7273(6) 0.6178(5) 0.7171(4) 0.1445(18) Uani 1 1 d . . . . .
H15A H 0.692175 0.527382 0.710813 0.217 Uiso 1 1 calc GR . . . .
H15B H 0.796887 0.661379 0.643646 0.217 Uiso 1 1 calc GR . . . .
H15C H 0.643472 0.684125 0.729233 0.217 Uiso 1 1 calc GR . . . .
C14 C 0.7195(6) 0.5060(5) 0.9315(4) 0.158(2) Uani 1 1 d . . . . .
H14A H 0.640362 0.566307 0.964158 0.237 Uiso 1 1 calc GR . . . .
H14B H 0.787242 0.474488 0.986448 0.237 Uiso 1 1 calc GR . . . .
H14C H 0.676943 0.421512 0.920871 0.237 Uiso 1 1 calc GR . . . .
C16 C 0.9315(5) 0.6388(5) 0.8105(8) 0.158(3) Uani 1 1 d . . . . .
H16 H 0.962864 0.703204 0.734550 0.190 Uiso 0.346(18) 1 calc R . P A 1
H16A H 0.945401 0.610516 0.890243 0.190 Uiso 0.654(18) 1 calc R . P A 2
O5B O 1.0177(9) 0.6309(9) 0.8642(13) 0.090(4) Uani 0.346(18) 1 d . . P A 1
O5A O 1.0235(6) 0.6914(10) 0.7639(14) 0.146(5) Uani 0.654(18) 1 d . . P A 2


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4291(16) . ?
S1 O4 1.4279(15) . ?
S1 N3 1.6278(17) . ?
S1 C10 1.740(2) . ?
S2 C9 1.708(2) . ?
S2 C12 1.703(3) . ?
O1 C6 1.244(2) . ?
O2 C8 1.269(2) . ?
N3 C7 1.450(2) . ?
N3 C13 1.471(3) . ?
N2 H2 0.8600 . ?
N2 C5 1.360(3) . ?
N2 C6 1.386(2) . ?
N1 H1 0.8600 . ?
N1 C5 1.337(3) . ?
N1 C1 1.353(3) . ?
C5 C4 1.389(3) . ?
C9 C8 1.477(3) . ?
C9 C10 1.367(3) . ?
C7 C6 1.423(3) . ?
C7 C8 1.400(3) . ?
C10 C11 1.416(3) . ?
N4 C15 1.407(4) . ?
N4 C14 1.434(5) . ?
N4 C16 1.303(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.365(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.356(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.352(3) . ?
C2 H2A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16 0.9300 . ?
C16 H16A 0.9300 . ?
C16 O5B 1.092(11) . ?
C16 O5A 0.983(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N3 107.93(9) . . ?
O3 S1 C10 108.75(10) . . ?
O4 S1 O3 118.48(10) . . ?
O4 S1 N3 108.44(10) . . ?
O4 S1 C10 110.37(10) . . ?
N3 S1 C10 101.49(9) . . ?
C12 S2 C9 91.78(11) . . ?
C7 N3 S1 115.56(13) . . ?
C7 N3 C13 114.51(16) . . ?
C13 N3 S1 117.59(14) . . ?
C5 N2 H2 116.6 . . ?
C5 N2 C6 126.73(18) . . ?
C6 N2 H2 116.6 . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 122.97(19) . . ?
C1 N1 H1 118.5 . . ?
N2 C5 C4 121.9(2) . . ?
N1 C5 N2 119.80(18) . . ?
N1 C5 C4 118.32(19) . . ?
C8 C9 S2 122.70(15) . . ?
C10 C9 S2 110.54(15) . . ?
C10 C9 C8 126.70(19) . . ?
C6 C7 N3 114.14(17) . . ?
C8 C7 N3 121.01(17) . . ?
C8 C7 C6 124.55(18) . . ?
O1 C6 N2 120.63(18) . . ?
O1 C6 C7 124.64(18) . . ?
N2 C6 C7 114.72(18) . . ?
O2 C8 C9 118.14(18) . . ?
O2 C8 C7 125.48(19) . . ?
C7 C8 C9 116.34(17) . . ?
C9 C10 S1 116.93(15) . . ?
C9 C10 C11 113.94(19) . . ?
C11 C10 S1 129.09(17) . . ?
C15 N4 C14 117.3(4) . . ?
C16 N4 C15 124.0(5) . . ?
C16 N4 C14 118.6(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C10 C11 H11 124.7 . . ?
C12 C11 C10 110.7(2) . . ?
C12 C11 H11 124.7 . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 N1 119.7(2) . . ?
C2 C1 H1A 120.1 . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2A 120.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C12 H12 123.5 . . ?
C11 C12 S2 113.05(18) . . ?
C11 C12 H12 123.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C16 H16 109.2 . . ?
N4 C16 H16A 104.5 . . ?
O5B C16 N4 141.7(11) . . ?
O5B C16 H16 109.2 . . ?
O5A C16 N4 151.0(13) . . ?
O5A C16 H16A 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.86 1.88 2.602(2) 141.2 . yes
N1 H1 O1 0.86 2.17 2.871(2) 137.9 2_566 yes
N1 H1 O1 0.86 1.97 2.620(2) 131.8 . yes

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N3 C7 C6 -141.06(16) . . . . ?
S1 N3 C7 C8 45.1(2) . . . . ?
S1 C10 C11 C12 -177.67(19) . . . . ?
S2 C9 C8 O2 -14.5(3) . . . . ?
S2 C9 C8 C7 167.80(15) . . . . ?
S2 C9 C10 S1 177.26(11) . . . . ?
S2 C9 C10 C11 -0.4(3) . . . . ?
O3 S1 N3 C7 62.41(16) . . . . ?
O3 S1 N3 C13 -157.35(16) . . . . ?
O3 S1 C10 C9 -82.94(19) . . . . ?
O3 S1 C10 C11 94.3(2) . . . . ?
O4 S1 N3 C7 -168.08(14) . . . . ?
O4 S1 N3 C13 -27.83(19) . . . . ?
O4 S1 C10 C9 145.51(17) . . . . ?
O4 S1 C10 C11 -37.2(3) . . . . ?
N3 S1 C10 C9 30.68(19) . . . . ?
N3 S1 C10 C11 -152.1(2) . . . . ?
N3 C7 C6 O1 6.1(3) . . . . ?
N3 C7 C6 N2 -172.22(17) . . . . ?
N3 C7 C8 O2 174.60(19) . . . . ?
N3 C7 C8 C9 -7.9(3) . . . . ?
N2 C5 C4 C3 178.1(2) . . . . ?
N1 C5 C4 C3 -1.3(3) . . . . ?
N1 C1 C2 C3 -1.2(4) . . . . ?
C5 N2 C6 O1 -3.2(3) . . . . ?
C5 N2 C6 C7 175.2(2) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C9 S2 C12 C11 -1.0(2) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C6 N2 C5 N1 5.5(3) . . . . ?
C6 N2 C5 C4 -173.9(2) . . . . ?
C6 C7 C8 O2 1.4(3) . . . . ?
C6 C7 C8 C9 178.93(19) . . . . ?
C8 C9 C10 S1 0.3(3) . . . . ?
C8 C9 C10 C11 -177.4(2) . . . . ?
C8 C7 C6 O1 179.7(2) . . . . ?
C8 C7 C6 N2 1.4(3) . . . . ?
C10 S1 N3 C7 -51.83(16) . . . . ?
C10 S1 N3 C13 88.42(17) . . . . ?
C10 C9 C8 O2 162.2(2) . . . . ?
C10 C9 C8 C7 -15.6(3) . . . . ?
C10 C11 C12 S2 1.0(3) . . . . ?
C4 C3 C2 C1 1.5(4) . . . . ?
C1 N1 C5 N2 -177.8(2) . . . . ?
C1 N1 C5 C4 1.7(3) . . . . ?
C13 N3 C7 C6 77.5(2) . . . . ?
C13 N3 C7 C8 -96.4(2) . . . . ?
C12 S2 C9 C8 177.92(19) . . . . ?
C12 S2 C9 C10 0.79(18) . . . . ?
C15 N4 C16 O5B -173.7(9) . . . . ?
C15 N4 C16 O5A -5.6(12) . . . . ?
C14 N4 C16 O5B 9.6(11) . . . . ?
C14 N4 C16 O5A 177.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.814
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMFA'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tnx_chcl3_III
_database_code_depnum_ccdc_archive 'CCDC 1904022'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'tenoxicam  chloroform III solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O4 S2, C H Cl3'
_chemical_formula_sum            'C14 H12 Cl3 N3 O4 S2'
_chemical_formula_weight         456.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0021 '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'
Cl Cl 0.1752 0.1990 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0149 0.0078 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1474 0.1548 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.579(3)
_cell_length_b                   10.135(2)
_cell_length_c                   14.880(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.58(3)
_cell_angle_gamma                90
_cell_volume                     1831.3(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      62.018
_cell_measurement_theta_min      3.746
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    1.037
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17905
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        28.439
_diffrn_reflns_theta_max         31.009
_diffrn_reflns_theta_min         1.873
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       /f
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7937
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3593
_reflns_number_total             4021
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+1.8294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C4(H4), C2(H2A), C1(H1A), C11(H11), C3(H3), C12(H12)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25364(4) 0.16931(5) 0.68506(4) 0.02317(14) Uani 1 1 d . . . . .
S2 S 0.05269(5) 0.40120(6) 0.43571(4) 0.02657(14) Uani 1 1 d . . . . .
Cl2 Cl 0.20697(5) 0.65664(6) 0.35327(5) 0.03248(15) Uani 1 1 d . . . . .
Cl3 Cl 0.06387(5) 0.87197(6) 0.34536(5) 0.03238(15) Uani 1 1 d . . . . .
Cl1 Cl 0.28931(5) 0.86807(7) 0.50112(5) 0.04031(17) Uani 1 1 d . . . . .
O4 O 0.21063(14) 0.05859(15) 0.71635(13) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.23034(13) 0.57656(15) 0.59179(12) 0.0264(3) Uani 1 1 d . . . . .
O1 O 0.42286(13) 0.46319(15) 0.89212(12) 0.0260(3) Uani 1 1 d . . . . .
O3 O 0.35526(13) 0.15433(15) 0.67901(13) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.37384(16) 0.62970(17) 0.77445(15) 0.0236(4) Uani 1 1 d . . . . .
H2 H 0.332387 0.649745 0.710976 0.028 Uiso 1 1 calc R . . . .
N1 N 0.50341(15) 0.70430(18) 0.93226(14) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.500098 0.626216 0.956629 0.028 Uiso 1 1 calc R . . . .
N3 N 0.26620(15) 0.29413(18) 0.75938(14) 0.0228(4) Uani 1 1 d . . . . .
C6 C 0.36552(17) 0.5013(2) 0.80418(17) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.44001(17) 0.7271(2) 0.83428(17) 0.0220(4) Uani 1 1 d . . . . .
C8 C 0.22502(17) 0.4626(2) 0.62551(17) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.28650(17) 0.4206(2) 0.72562(17) 0.0222(4) Uani 1 1 d . . . . .
C4 C 0.44225(18) 0.8529(2) 0.79579(18) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.395944 0.872900 0.727256 0.029 Uiso 1 1 calc R . . . .
C9 C 0.15211(18) 0.3628(2) 0.55414(18) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.15369(18) 0.2291(2) 0.57016(17) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.18592(19) 0.3017(2) 0.80151(19) 0.0285(5) Uani 1 1 d . . . . .
H13A H 0.114805 0.332467 0.749468 0.043 Uiso 1 1 calc GR . . . .
H13B H 0.212946 0.363453 0.858151 0.043 Uiso 1 1 calc GR . . . .
H13C H 0.176961 0.214057 0.824742 0.043 Uiso 1 1 calc GR . . . .
C2 C 0.57950(19) 0.9183(2) 0.95995(18) 0.0273(5) Uani 1 1 d . . . . .
H2A H 0.628984 0.982577 1.003110 0.033 Uiso 1 1 calc R . . . .
C1 C 0.57253(18) 0.7961(2) 0.99570(18) 0.0260(5) Uani 1 1 d . . . . .
H1A H 0.615889 0.775533 1.064662 0.031 Uiso 1 1 calc R . . . .
C11 C 0.0738(2) 0.1575(2) 0.48872(18) 0.0280(5) Uani 1 1 d . . . . .
H11 H 0.064067 0.064611 0.488239 0.034 Uiso 1 1 calc R . . . .
C3 C 0.51242(19) 0.9468(2) 0.85866(18) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.515366 1.031773 0.833065 0.032 Uiso 1 1 calc R . . . .
C12 C 0.01252(19) 0.2391(2) 0.41107(18) 0.0298(5) Uani 1 1 d . . . . .
H12 H -0.046072 0.209723 0.349886 0.036 Uiso 1 1 calc R . . . .
C14 C 0.17425(19) 0.7703(2) 0.42575(18) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.150577 0.720093 0.470602 0.033 Uiso 1 1 calc R . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4354(16) . ?
S1 O3 1.4305(17) . ?
S1 N3 1.6382(19) . ?
S1 C10 1.748(2) . ?
S2 C9 1.718(2) . ?
S2 C12 1.718(3) . ?
Cl2 C14 1.766(2) . ?
Cl3 C14 1.770(2) . ?
Cl1 C14 1.764(2) . ?
O2 C8 1.274(3) . ?
O1 C6 1.247(3) . ?
N2 H2 0.8800 . ?
N2 C6 1.395(3) . ?
N2 C5 1.363(3) . ?
N1 H1 0.8800 . ?
N1 C5 1.340(3) . ?
N1 C1 1.358(3) . ?
N3 C7 1.448(3) . ?
N3 C13 1.483(3) . ?
C6 C7 1.437(3) . ?
C5 C4 1.404(3) . ?
C8 C7 1.409(3) . ?
C8 C9 1.480(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.375(3) . ?
C9 C10 1.374(3) . ?
C10 C11 1.413(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 H2A 0.9500 . ?
C2 C1 1.367(3) . ?
C2 C3 1.399(3) . ?
C1 H1A 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.361(4) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 N3 108.62(10) . . ?
O4 S1 C10 109.74(10) . . ?
O3 S1 O4 118.78(10) . . ?
O3 S1 N3 108.21(10) . . ?
O3 S1 C10 108.90(11) . . ?
N3 S1 C10 101.14(10) . . ?
C9 S2 C12 91.78(11) . . ?
C6 N2 H2 116.9 . . ?
C5 N2 H2 116.9 . . ?
C5 N2 C6 126.3(2) . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 123.07(19) . . ?
C1 N1 H1 118.5 . . ?
C7 N3 S1 115.35(15) . . ?
C7 N3 C13 113.03(17) . . ?
C13 N3 S1 116.81(15) . . ?
O1 C6 N2 121.37(19) . . ?
O1 C6 C7 124.43(19) . . ?
N2 C6 C7 114.20(19) . . ?
N2 C5 C4 121.3(2) . . ?
N1 C5 N2 120.04(19) . . ?
N1 C5 C4 118.7(2) . . ?
O2 C8 C7 125.4(2) . . ?
O2 C8 C9 118.3(2) . . ?
C7 C8 C9 116.24(19) . . ?
C6 C7 N3 114.24(19) . . ?
C8 C7 N3 121.31(19) . . ?
C8 C7 C6 124.20(19) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C8 C9 S2 123.20(17) . . ?
C10 C9 S2 110.21(17) . . ?
C10 C9 C8 126.6(2) . . ?
C9 C10 S1 117.17(17) . . ?
C9 C10 C11 114.3(2) . . ?
C11 C10 S1 128.53(18) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
N1 C1 C2 119.8(2) . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C10 C11 H11 124.5 . . ?
C12 C11 C10 111.0(2) . . ?
C12 C11 H11 124.5 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
S2 C12 H12 123.7 . . ?
C11 C12 S2 112.66(18) . . ?
C11 C12 H12 123.7 . . ?
Cl2 C14 Cl3 109.60(13) . . ?
Cl2 C14 H14 108.6 . . ?
Cl3 C14 H14 108.6 . . ?
Cl1 C14 Cl2 111.19(13) . . ?
Cl1 C14 Cl3 110.12(13) . . ?
Cl1 C14 H14 108.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.88 1.85 2.595(3) 141.4 . yes
N1 H1 O1 0.88 2.21 2.893(2) 134.5 3_667 yes
N1 H1 O1 0.88 1.96 2.634(2) 132.1 . yes

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N3 C7 C6 -139.58(17) . . . . ?
S1 N3 C7 C8 46.0(3) . . . . ?
S1 C10 C11 C12 -178.30(18) . . . . ?
S2 C9 C10 S1 177.41(12) . . . . ?
S2 C9 C10 C11 -1.4(3) . . . . ?
O4 S1 N3 C7 -167.59(15) . . . . ?
O4 S1 N3 C13 -31.18(19) . . . . ?
O4 S1 C10 C9 146.19(18) . . . . ?
O4 S1 C10 C11 -35.2(2) . . . . ?
O2 C8 C7 N3 173.2(2) . . . . ?
O2 C8 C7 C6 -0.7(4) . . . . ?
O2 C8 C9 S2 -14.7(3) . . . . ?
O2 C8 C9 C10 164.2(2) . . . . ?
O1 C6 C7 N3 8.3(3) . . . . ?
O1 C6 C7 C8 -177.4(2) . . . . ?
O3 S1 N3 C7 62.20(18) . . . . ?
O3 S1 N3 C13 -161.38(16) . . . . ?
O3 S1 C10 C9 -82.2(2) . . . . ?
O3 S1 C10 C11 96.4(2) . . . . ?
N2 C6 C7 N3 -171.57(18) . . . . ?
N2 C6 C7 C8 2.7(3) . . . . ?
N2 C5 C4 C3 -178.4(2) . . . . ?
N1 C5 C4 C3 2.6(3) . . . . ?
N3 S1 C10 C9 31.6(2) . . . . ?
N3 S1 C10 C11 -149.8(2) . . . . ?
C6 N2 C5 N1 -1.5(3) . . . . ?
C6 N2 C5 C4 179.5(2) . . . . ?
C5 N2 C6 O1 -1.6(3) . . . . ?
C5 N2 C6 C7 178.3(2) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C5 C4 C3 C2 -1.0(3) . . . . ?
C8 C9 C10 S1 -1.6(3) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C7 C8 C9 S2 167.65(17) . . . . ?
C7 C8 C9 C10 -13.5(3) . . . . ?
C9 S2 C12 C11 -1.4(2) . . . . ?
C9 C8 C7 N3 -9.4(3) . . . . ?
C9 C8 C7 C6 176.7(2) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 S1 N3 C7 -52.15(17) . . . . ?
C10 S1 N3 C13 84.27(17) . . . . ?
C10 C11 C12 S2 0.9(3) . . . . ?
C13 N3 C7 C6 82.4(2) . . . . ?
C13 N3 C7 C8 -92.1(2) . . . . ?
C1 N1 C5 N2 178.9(2) . . . . ?
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C3 C2 C1 N1 1.7(3) . . . . ?
C12 S2 C9 C8 -179.4(2) . . . . ?
C12 S2 C9 C10 1.58(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform under -18 Celsius degree'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tnx_chcl3_I
_database_code_depnum_ccdc_archive 'CCDC 1890995'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'tenoxicam chloroform I solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 N3 O4 S2), 2(C H Cl3)'
_chemical_formula_sum            'C28 H24 Cl6 N6 O8 S4'
_chemical_formula_weight         913.47
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6019(12)
_cell_length_b                   12.7810(10)
_cell_length_c                   28.841(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.076(10)
_cell_angle_gamma                90
_cell_volume                     3905.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.3050
_cell_measurement_theta_min      3.4580
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform under room temperature'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2467
_diffrn_reflns_av_unetI/netI     0.1322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            54415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.231
_diffrn_ambient_temperature      293(3)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00   2.00   1.00   60.00    --  -11.27 127.00  94.42   72
  2  ω    -20.00  54.00   1.00   60.00    --   11.43  77.00 150.00   74
  3  ω    -18.00  58.00   1.00   60.00    --   11.43  57.00 -90.00   76
  4  ω    -58.00  41.00   1.00   60.00    --   11.43 -57.00-120.00   99
  5  ω    -61.00  41.00   1.00   60.00    --   11.43 -57.00  90.00  102
  6  ω    -65.00  45.00   1.00   60.00    --   11.43 -77.00   0.00  110
  7  ω    -14.00  90.00   1.00   60.00    --   11.43  77.00   0.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2586
_reflns_number_total             6880
_reflns_special_details          
;
One chlorform molecule has a common C-H moiety (C14A H14A,H14B) with three 
 disordered chlorine sites (Cl1 and Cl1A, Cl2 and Cl2A, Cl3 and Cl3A) with 0.64(4) and 0.36(4) 
 atom occupancy ratio. Second chloroform molecule is completely disordered 
 (atom occupancy ratio is 0.545(13) and 0.455(13)). It was refine isotropically 
 with constraining the C-Cl distances equal d=1.78(2) angstrom.
 
Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         6880
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2576
_refine_ls_R_factor_gt           0.1163
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1678P)²+8.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3158
_refine_ls_wR_factor_ref         0.3957
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl4-C141 = Cl6-C141 = Cl5-C141 = Cl5A-C142 = Cl4A-C142 = Cl6A-C142
 1.78 with sigma of 0.02
3. Others
 Sof(H14B)=Sof(Cl2A)=Sof(Cl3A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl2)=Sof(Cl3)=Sof(Cl1)=Sof(H14A)=FVAR(1)
 Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=Sof(C142)=Sof(H142)=1-FVAR(2)
 Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(C141)=Sof(H141)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14A(H14B), C141(H141), C142(H142)
4.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1B(H1B), N2A(H2A), N2B(H2B), C2A(H2AA), C3A(H3A), C11A(H11A),
 C12A(H12A), C4A(H4A), C4B(H4B), C2B(H2BA), C11B(H11B), C1A(H1AA), C3B(H3B),
 C12B(H12B), C1B(H1BA)
4.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2A S 0.0736(3) 0.7459(2) 0.38459(9) 0.0708(9) Uani 1 1 d . . . . .
S1A S 0.1433(3) 0.8446(2) 0.52189(9) 0.0741(10) Uani 1 1 d . . . . .
S1B S 0.1598(4) 0.1690(2) 0.73255(10) 0.0871(11) Uani 1 1 d . . . . .
S2B S 0.1023(4) 0.2607(3) 0.86890(10) 0.0982(12) Uani 1 1 d . . . . .
O1A O 0.2518(7) 0.5625(5) 0.5831(2) 0.074(2) Uani 1 1 d . . . . .
Cl2 Cl 0.5942(19) 1.1427(14) 0.6331(7) 0.169(7) Uani 0.63(4) 1 d . . P A 1
O2A O 0.1084(7) 0.5565(5) 0.4456(2) 0.075(2) Uani 1 1 d . . . . .
O1B O 0.2737(8) 0.4500(5) 0.6757(2) 0.081(2) Uani 1 1 d . . . . .
Cl3 Cl 0.5936(13) 0.9958(12) 0.5600(4) 0.145(6) Uani 0.63(4) 1 d . . P A 1
N1A N 0.2402(8) 0.3550(6) 0.5846(3) 0.065(2) Uani 1 1 d . . . . .
H1A H 0.244481 0.409910 0.601789 0.078 Uiso 1 1 calc R . . . .
O4A O 0.2122(9) 0.9381(5) 0.5342(3) 0.097(3) Uani 1 1 d . . . . .
Cl1 Cl 0.517(2) 0.9280(19) 0.6458(7) 0.209(9) Uani 0.63(4) 1 d . . P A 1
O2B O 0.1480(9) 0.4512(6) 0.8117(2) 0.098(3) Uani 1 1 d . . . . .
N1B N 0.2410(9) 0.6551(6) 0.6736(3) 0.076(3) Uani 1 1 d . . . . .
H1B H 0.251594 0.599929 0.657121 0.092 Uiso 1 1 calc R . . . .
N2A N 0.1902(9) 0.4620(6) 0.5210(3) 0.073(3) Uani 1 1 d . . . . .
H2A H 0.159345 0.463808 0.493043 0.087 Uiso 1 1 calc R . . . .
N3A N 0.2350(10) 0.7445(6) 0.5314(3) 0.070(3) Uani 1 1 d . . . . .
O3B O 0.0450(10) 0.1965(7) 0.7085(3) 0.109(3) Uani 1 1 d . . . . .
C10A C 0.1172(10) 0.8386(7) 0.4628(3) 0.059(3) Uani 1 1 d . . . . .
C6A C 0.2135(10) 0.5589(7) 0.5419(3) 0.063(3) Uani 1 1 d . . . . .
O3A O 0.0287(9) 0.8252(6) 0.5439(3) 0.093(3) Uani 1 1 d . . . . .
C9A C 0.1159(10) 0.7420(8) 0.4429(3) 0.061(3) Uani 1 1 d . . . . .
N2B N 0.2188(10) 0.5493(7) 0.7379(3) 0.085(3) Uani 1 1 d . . . . .
H2B H 0.198879 0.546359 0.766471 0.102 Uiso 1 1 calc R . . . .
N3B N 0.2596(10) 0.2644(6) 0.7265(3) 0.073(3) Uani 1 1 d . . . . .
C8A C 0.1414(10) 0.6411(7) 0.4666(3) 0.058(3) Uani 1 1 d . . . . .
O4B O 0.2203(10) 0.0736(6) 0.7205(3) 0.116(3) Uani 1 1 d . . . . .
C10B C 0.1342(11) 0.1713(8) 0.7909(4) 0.073(3) Uani 1 1 d . . . . .
C2A C 0.2574(12) 0.1719(8) 0.5796(4) 0.082(4) Uani 1 1 d . . . . .
H2AA H 0.272279 0.106764 0.593107 0.099 Uiso 1 1 calc R . . . .
C5A C 0.2096(10) 0.3672(7) 0.5389(3) 0.057(3) Uani 1 1 d . . . . .
C3A C 0.2267(13) 0.1816(8) 0.5330(5) 0.091(4) Uani 1 1 d . . . . .
H3A H 0.222701 0.121758 0.514626 0.109 Uiso 1 1 calc R . . . .
C8B C 0.1722(11) 0.3677(8) 0.7901(3) 0.069(3) Uani 1 1 d . . . . .
C7A C 0.1907(11) 0.6465(7) 0.5121(3) 0.065(3) Uani 1 1 d . . . . .
C9B C 0.1416(11) 0.2683(9) 0.8127(3) 0.075(3) Uani 1 1 d . . . . .
C11A C 0.0857(10) 0.9180(8) 0.4307(4) 0.072(3) Uani 1 1 d . . . . .
H11A H 0.081844 0.988559 0.438387 0.086 Uiso 1 1 calc R . . . .
C5B C 0.2232(11) 0.6448(8) 0.7193(4) 0.073(3) Uani 1 1 d . . . . .
C12A C 0.0612(11) 0.8804(8) 0.3867(4) 0.076(3) Uani 1 1 d . . . . .
H12A H 0.040519 0.922314 0.361213 0.092 Uiso 1 1 calc R . . . .
C4A C 0.2018(12) 0.2776(9) 0.5127(4) 0.088(4) Uani 1 1 d . . . . .
H4A H 0.179709 0.281572 0.481234 0.106 Uiso 1 1 calc R . . . .
C6B C 0.2432(10) 0.4515(7) 0.7161(4) 0.064(3) Uani 1 1 d . . . . .
C7B C 0.2197(12) 0.3646(7) 0.7454(3) 0.076(3) Uani 1 1 d . . . . .
C4B C 0.2117(12) 0.7335(9) 0.7456(4) 0.090(4) Uani 1 1 d . . . . .
H4B H 0.201950 0.728554 0.777416 0.108 Uiso 1 1 calc R . . . .
C2B C 0.2294(12) 0.8376(8) 0.6778(4) 0.085(4) Uani 1 1 d . . . . .
H2BA H 0.230223 0.902811 0.663509 0.102 Uiso 1 1 calc R . . . .
C11B C 0.0937(11) 0.0924(11) 0.8207(4) 0.090(4) Uani 1 1 d . . . . .
H11B H 0.081742 0.023127 0.811749 0.109 Uiso 1 1 calc R . . . .
C1A C 0.2650(11) 0.2596(9) 0.6048(4) 0.079(3) Uani 1 1 d . . . . .
H1AA H 0.287140 0.255939 0.636255 0.095 Uiso 1 1 calc R . . . .
C13A C 0.3733(13) 0.7598(9) 0.5249(4) 0.092(4) Uani 1 1 d . . . . .
H13A H 0.390691 0.753736 0.492618 0.138 Uiso 1 1 calc GR . . . .
H13B H 0.419942 0.707357 0.542167 0.138 Uiso 1 1 calc GR . . . .
H13C H 0.398008 0.827912 0.535921 0.138 Uiso 1 1 calc GR . . . .
C3B C 0.2146(14) 0.8291(10) 0.7245(5) 0.099(4) Uani 1 1 d . . . . .
H3B H 0.206447 0.889411 0.742157 0.119 Uiso 1 1 calc R . . . .
C12B C 0.0744(12) 0.1279(11) 0.8629(5) 0.098(4) Uani 1 1 d . . . . .
H12B H 0.048489 0.085576 0.887016 0.118 Uiso 1 1 calc R . . . .
C1B C 0.2427(12) 0.7491(9) 0.6529(4) 0.083(4) Uani 1 1 d . . . . .
H1BA H 0.253215 0.753395 0.621070 0.100 Uiso 1 1 calc R . . . .
C13B C 0.3945(15) 0.2389(10) 0.7349(5) 0.112(5) Uani 1 1 d . . . . .
H13D H 0.409243 0.221160 0.767031 0.168 Uiso 1 1 calc GR . . . .
H13E H 0.445159 0.298304 0.727363 0.168 Uiso 1 1 calc GR . . . .
H13F H 0.416811 0.180538 0.715919 0.168 Uiso 1 1 calc GR . . . .
C14A C 0.6176(15) 1.0092(12) 0.6196(5) 0.125(5) Uani 1 1 d . . . . .
H14A H 0.704635 0.989491 0.628318 0.150 Uiso 0.63(4) 1 calc R . P A 1
H14B H 0.705603 0.995394 0.629332 0.150 Uiso 0.37(4) 1 calc R . P A 2
Cl4 Cl 0.5672(9) 0.6284(7) 0.6321(4) 0.121(3) Uiso 0.539(15) 1 d D . P B 1
Cl5 Cl 0.5490(10) 0.4719(10) 0.5568(4) 0.160(5) Uiso 0.539(15) 1 d D . P B 1
Cl6 Cl 0.6185(13) 0.4072(12) 0.6483(6) 0.203(6) Uiso 0.539(15) 1 d D . P B 1
C141 C 0.631(2) 0.5068(14) 0.6079(6) 0.121(10) Uiso 0.539(15) 1 d D . P B 1
H141 H 0.720611 0.517259 0.601307 0.145 Uiso 0.539(15) 1 calc R . P B 1
Cl2A Cl 0.605(4) 1.140(3) 0.6179(17) 0.223(18) Uani 0.37(4) 1 d . . P A 2
Cl3A Cl 0.594(4) 0.944(7) 0.575(3) 0.39(3) Uani 0.37(4) 1 d . . P A 2
Cl1A Cl 0.526(3) 0.966(4) 0.6670(19) 0.220(18) Uani 0.37(4) 1 d . . P A 2
Cl4A Cl 0.5994(13) 0.6292(10) 0.6098(6) 0.164(5) Uiso 0.461(15) 1 d D . P B 2
Cl5A Cl 0.5673(16) 0.4154(16) 0.5819(7) 0.214(7) Uiso 0.461(15) 1 d D . P B 2
Cl6A Cl 0.6123(13) 0.4527(13) 0.6754(6) 0.179(6) Uiso 0.461(15) 1 d D . P B 2
C142 C 0.529(3) 0.5045(16) 0.6260(7) 0.135(13) Uiso 0.461(15) 1 d D . P B 2
H142 H 0.438025 0.509600 0.630271 0.163 Uiso 0.461(15) 1 calc R . P B 2


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2A C9A 1.725(10) . ?
S2A C12A 1.726(10) . ?
S1A O4A 1.439(7) . ?
S1A N3A 1.624(9) . ?
S1A C10A 1.717(10) . ?
S1A O3A 1.413(9) . ?
S1B O3B 1.424(10) . ?
S1B N3B 1.627(10) . ?
S1B O4B 1.427(8) . ?
S1B C10B 1.716(11) . ?
S2B C9B 1.691(11) . ?
S2B C12B 1.731(15) . ?
O1A C6A 1.241(10) . ?
Cl2 C14A 1.77(2) . ?
O2A C8A 1.283(10) . ?
O1B C6B 1.222(11) . ?
Cl3 C14A 1.74(2) . ?
N1A H1A 0.8600 . ?
N1A C5A 1.353(11) . ?
N1A C1A 1.374(12) . ?
Cl1 C14A 1.68(2) . ?
O2B C8B 1.267(11) . ?
N1B H1B 0.8600 . ?
N1B C5B 1.345(13) . ?
N1B C1B 1.342(12) . ?
N2A H2A 0.8600 . ?
N2A C6A 1.395(12) . ?
N2A C5A 1.330(11) . ?
N3A C7A 1.443(12) . ?
N3A C13A 1.497(15) . ?
C10A C9A 1.361(13) . ?
C10A C11A 1.408(13) . ?
C6A C7A 1.427(13) . ?
C9A C8A 1.481(13) . ?
N2B H2B 0.8600 . ?
N2B C5B 1.334(12) . ?
N2B C6B 1.426(12) . ?
N3B C7B 1.460(12) . ?
N3B C13B 1.479(16) . ?
C8A C7A 1.396(13) . ?
C10B C9B 1.390(14) . ?
C10B C11B 1.401(15) . ?
C2A H2AA 0.9300 . ?
C2A C3A 1.379(16) . ?
C2A C1A 1.335(15) . ?
C5A C4A 1.374(14) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.380(15) . ?
C8B C9B 1.468(15) . ?
C8B C7B 1.402(14) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.371(14) . ?
C5B C4B 1.372(14) . ?
C12A H12A 0.9300 . ?
C4A H4A 0.9300 . ?
C6B C7B 1.423(13) . ?
C4B H4B 0.9300 . ?
C4B C3B 1.367(16) . ?
C2B H2BA 0.9300 . ?
C2B C3B 1.364(15) . ?
C2B C1B 1.350(14) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.322(16) . ?
C1A H1AA 0.9300 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C3B H3B 0.9300 . ?
C12B H12B 0.9300 . ?
C1B H1BA 0.9300 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A Cl2A 1.67(4) . ?
C14A Cl3A 1.54(4) . ?
C14A Cl1A 1.79(4) . ?
Cl4 C141 1.844(17) . ?
Cl5 C141 1.743(17) . ?
Cl6 C141 1.735(17) . ?
C141 H141 0.9800 . ?
Cl4A C142 1.827(18) . ?
Cl5A C142 1.764(18) . ?
Cl6A C142 1.776(18) . ?
C142 H142 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A S2A C12A 90.6(5) . . ?
O4A S1A N3A 108.5(5) . . ?
O4A S1A C10A 110.2(5) . . ?
N3A S1A C10A 101.9(4) . . ?
O3A S1A O4A 118.1(5) . . ?
O3A S1A N3A 107.8(5) . . ?
O3A S1A C10A 109.1(5) . . ?
O3B S1B N3B 108.1(5) . . ?
O3B S1B O4B 118.4(6) . . ?
O3B S1B C10B 108.1(6) . . ?
N3B S1B C10B 102.7(5) . . ?
O4B S1B N3B 108.4(6) . . ?
O4B S1B C10B 110.0(5) . . ?
C9B S2B C12B 90.5(6) . . ?
C5A N1A H1A 118.3 . . ?
C5A N1A C1A 123.4(9) . . ?
C1A N1A H1A 118.3 . . ?
C5B N1B H1B 119.0 . . ?
C1B N1B H1B 119.0 . . ?
C1B N1B C5B 121.9(9) . . ?
C6A N2A H2A 115.9 . . ?
C5A N2A H2A 115.9 . . ?
C5A N2A C6A 128.1(8) . . ?
C7A N3A S1A 115.8(7) . . ?
C7A N3A C13A 111.8(8) . . ?
C13A N3A S1A 117.4(7) . . ?
C9A C10A S1A 117.3(7) . . ?
C9A C10A C11A 112.1(9) . . ?
C11A C10A S1A 130.3(8) . . ?
O1A C6A N2A 119.5(8) . . ?
O1A C6A C7A 126.1(8) . . ?
N2A C6A C7A 114.3(9) . . ?
C10A C9A S2A 112.6(7) . . ?
C10A C9A C8A 126.5(9) . . ?
C8A C9A S2A 120.8(7) . . ?
C5B N2B H2B 116.0 . . ?
C5B N2B C6B 128.0(9) . . ?
C6B N2B H2B 116.0 . . ?
C7B N3B S1B 114.8(8) . . ?
C7B N3B C13B 115.0(10) . . ?
C13B N3B S1B 116.5(7) . . ?
O2A C8A C9A 118.3(9) . . ?
O2A C8A C7A 124.9(8) . . ?
C7A C8A C9A 116.6(8) . . ?
C9B C10B S1B 116.7(8) . . ?
C9B C10B C11B 112.3(11) . . ?
C11B C10B S1B 130.6(10) . . ?
C3A C2A H2AA 121.2 . . ?
C1A C2A H2AA 121.2 . . ?
C1A C2A C3A 117.6(10) . . ?
N1A C5A C4A 116.6(9) . . ?
N2A C5A N1A 120.7(8) . . ?
N2A C5A C4A 122.7(10) . . ?
C2A C3A H3A 119.1 . . ?
C2A C3A C4A 121.9(10) . . ?
C4A C3A H3A 119.1 . . ?
O2B C8B C9B 117.3(10) . . ?
O2B C8B C7B 124.2(10) . . ?
C7B C8B C9B 118.4(9) . . ?
C6A C7A N3A 113.8(8) . . ?
C8A C7A N3A 120.6(8) . . ?
C8A C7A C6A 125.3(8) . . ?
C10B C9B S2B 111.7(8) . . ?
C10B C9B C8B 125.5(10) . . ?
C8B C9B S2B 122.7(8) . . ?
C10A C11A H11A 123.6 . . ?
C12A C11A C10A 112.9(10) . . ?
C12A C11A H11A 123.6 . . ?
N1B C5B C4B 118.6(10) . . ?
N2B C5B N1B 119.5(9) . . ?
N2B C5B C4B 121.9(11) . . ?
S2A C12A H12A 124.1 . . ?
C11A C12A S2A 111.7(8) . . ?
C11A C12A H12A 124.1 . . ?
C5A C4A C3A 120.0(11) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
O1B C6B N2B 119.4(9) . . ?
O1B C6B C7B 127.8(9) . . ?
C7B C6B N2B 112.7(9) . . ?
C8B C7B N3B 119.1(8) . . ?
C8B C7B C6B 126.9(9) . . ?
C6B C7B N3B 113.8(9) . . ?
C5B C4B H4B 120.4 . . ?
C3B C4B C5B 119.3(12) . . ?
C3B C4B H4B 120.4 . . ?
C3B C2B H2BA 120.8 . . ?
C1B C2B H2BA 120.8 . . ?
C1B C2B C3B 118.5(11) . . ?
C10B C11B H11B 123.9 . . ?
C12B C11B C10B 112.2(13) . . ?
C12B C11B H11B 123.9 . . ?
N1A C1A H1AA 119.8 . . ?
C2A C1A N1A 120.5(11) . . ?
C2A C1A H1AA 119.8 . . ?
N3A C13A H13A 109.5 . . ?
N3A C13A H13B 109.5 . . ?
N3A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B C4B 121.0(11) . . ?
C2B C3B H3B 119.5 . . ?
S2B C12B H12B 123.3 . . ?
C11B C12B S2B 113.3(10) . . ?
C11B C12B H12B 123.3 . . ?
N1B C1B C2B 120.7(11) . . ?
N1B C1B H1BA 119.7 . . ?
C2B C1B H1BA 119.7 . . ?
N3B C13B H13D 109.5 . . ?
N3B C13B H13E 109.5 . . ?
N3B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
Cl2 C14A H14A 109.3 . . ?
Cl3 C14A Cl2 107.2(11) . . ?
Cl3 C14A H14A 109.3 . . ?
Cl1 C14A Cl2 113.6(14) . . ?
Cl1 C14A Cl3 108.1(12) . . ?
Cl1 C14A H14A 109.3 . . ?
Cl2A C14A H14B 105.4 . . ?
Cl2A C14A Cl1A 106(2) . . ?
Cl3A C14A H14B 105.4 . . ?
Cl3A C14A Cl2A 120(4) . . ?
Cl3A C14A Cl1A 113(2) . . ?
Cl1A C14A H14B 105.4 . . ?
Cl4 C141 H141 109.3 . . ?
Cl5 C141 Cl4 110.8(11) . . ?
Cl5 C141 H141 109.3 . . ?
Cl6 C141 Cl4 108.9(12) . . ?
Cl6 C141 Cl5 109.3(13) . . ?
Cl6 C141 H141 109.3 . . ?
Cl4A C142 H142 112.7 . . ?
Cl5A C142 Cl4A 105.8(14) . . ?
Cl5A C142 Cl6A 102.5(14) . . ?
Cl5A C142 H142 112.7 . . ?
Cl6A C142 Cl4A 109.5(14) . . ?
Cl6A C142 H142 112.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.86 2.03 2.655(10) 129.3 . yes
N1A H1A O1B 0.86 2.20 2.905(11) 138.7 . yes
N1B H1B O1A 0.86 2.19 2.872(11) 136.3 . yes
N1B H1B O1B 0.86 2.00 2.645(10) 130.9 . yes
N2A H2A O2A 0.86 1.87 2.608(10) 142.3 . yes
N2B H2B O2B 0.86 1.88 2.606(11) 141.4 . yes

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2A C9A C8A O2A -13.2(14) . . . . ?
S2A C9A C8A C7A 171.9(8) . . . . ?
S1A N3A C7A C6A -140.0(8) . . . . ?
S1A N3A C7A C8A 45.5(13) . . . . ?
S1A C10A C9A S2A 174.1(6) . . . . ?
S1A C10A C9A C8A -3.5(15) . . . . ?
S1A C10A C11A C12A -174.4(9) . . . . ?
S1B N3B C7B C8B 47.3(13) . . . . ?
S1B N3B C7B C6B -137.0(9) . . . . ?
S1B C10B C9B S2B 175.2(6) . . . . ?
S1B C10B C9B C8B -1.5(16) . . . . ?
S1B C10B C11B C12B -174.2(10) . . . . ?
O1A C6A C7A N3A 9.4(17) . . . . ?
O1A C6A C7A C8A -176.5(11) . . . . ?
O2A C8A C7A N3A 174.7(10) . . . . ?
O2A C8A C7A C6A 0.9(18) . . . . ?
O1B C6B C7B N3B 11.9(18) . . . . ?
O1B C6B C7B C8B -172.8(12) . . . . ?
N1A C5A C4A C3A -1.0(17) . . . . ?
O4A S1A N3A C7A -167.7(7) . . . . ?
O4A S1A N3A C13A -32.1(9) . . . . ?
O4A S1A C10A C9A 146.7(9) . . . . ?
O4A S1A C10A C11A -39.3(12) . . . . ?
O2B C8B C9B S2B -11.6(15) . . . . ?
O2B C8B C9B C10B 164.7(11) . . . . ?
O2B C8B C7B N3B 171.9(11) . . . . ?
O2B C8B C7B C6B -3(2) . . . . ?
N1B C5B C4B C3B 2.0(19) . . . . ?
N2A C6A C7A N3A -170.1(9) . . . . ?
N2A C6A C7A C8A 4.1(17) . . . . ?
N2A C5A C4A C3A 178.0(11) . . . . ?
N3A S1A C10A C9A 31.7(10) . . . . ?
N3A S1A C10A C11A -154.4(10) . . . . ?
O3B S1B N3B C7B 61.0(8) . . . . ?
O3B S1B N3B C13B -160.4(9) . . . . ?
O3B S1B C10B C9B -82.7(10) . . . . ?
O3B S1B C10B C11B 89.8(12) . . . . ?
C10A S1A N3A C7A -51.5(9) . . . . ?
C10A S1A N3A C13A 84.1(8) . . . . ?
C10A C9A C8A O2A 164.1(10) . . . . ?
C10A C9A C8A C7A -10.7(16) . . . . ?
C10A C11A C12A S2A 1.2(13) . . . . ?
C6A N2A C5A N1A 9.6(17) . . . . ?
C6A N2A C5A C4A -169.4(11) . . . . ?
O3A S1A N3A C7A 63.3(8) . . . . ?
O3A S1A N3A C13A -161.1(8) . . . . ?
O3A S1A C10A C9A -82.1(9) . . . . ?
O3A S1A C10A C11A 91.8(11) . . . . ?
C9A S2A C12A C11A -1.5(9) . . . . ?
C9A C10A C11A C12A -0.2(14) . . . . ?
C9A C8A C7A N3A -10.8(15) . . . . ?
C9A C8A C7A C6A 175.4(10) . . . . ?
N2B C5B C4B C3B -178.8(12) . . . . ?
N2B C6B C7B N3B -172.3(10) . . . . ?
N2B C6B C7B C8B 3.0(17) . . . . ?
N3B S1B C10B C9B 31.3(10) . . . . ?
N3B S1B C10B C11B -156.1(11) . . . . ?
O4B S1B N3B C7B -169.5(8) . . . . ?
O4B S1B N3B C13B -30.9(10) . . . . ?
O4B S1B C10B C9B 146.5(9) . . . . ?
O4B S1B C10B C11B -40.9(13) . . . . ?
C10B S1B N3B C7B -53.1(8) . . . . ?
C10B S1B N3B C13B 85.5(9) . . . . ?
C10B C11B C12B S2B 0.9(14) . . . . ?
C2A C3A C4A C5A 1(2) . . . . ?
C5A N1A C1A C2A -1.2(17) . . . . ?
C5A N2A C6A O1A -3.7(18) . . . . ?
C5A N2A C6A C7A 175.7(10) . . . . ?
C3A C2A C1A N1A 1.3(19) . . . . ?
C9B S2B C12B C11B -0.2(11) . . . . ?
C9B C10B C11B C12B -1.4(15) . . . . ?
C9B C8B C7B N3B -11.6(17) . . . . ?
C9B C8B C7B C6B 173.4(11) . . . . ?
C11A C10A C9A S2A -1.0(12) . . . . ?
C11A C10A C9A C8A -178.5(10) . . . . ?
C5B N1B C1B C2B 1.6(19) . . . . ?
C5B N2B C6B O1B 1.0(18) . . . . ?
C5B N2B C6B C7B -175.2(12) . . . . ?
C5B C4B C3B C2B 0(2) . . . . ?
C12A S2A C9A C10A 1.4(9) . . . . ?
C12A S2A C9A C8A 179.1(9) . . . . ?
C6B N2B C5B N1B 6.7(18) . . . . ?
C6B N2B C5B C4B -172.4(12) . . . . ?
C7B C8B C9B S2B 171.6(9) . . . . ?
C7B C8B C9B C10B -12.0(18) . . . . ?
C11B C10B C9B S2B 1.3(13) . . . . ?
C11B C10B C9B C8B -175.4(11) . . . . ?
C1A N1A C5A N2A -178.1(10) . . . . ?
C1A N1A C5A C4A 1.0(16) . . . . ?
C1A C2A C3A C4A -1(2) . . . . ?
C13A N3A C7A C6A 82.0(12) . . . . ?
C13A N3A C7A C8A -92.5(12) . . . . ?
C3B C2B C1B N1B 0(2) . . . . ?
C12B S2B C9B C10B -0.6(10) . . . . ?
C12B S2B C9B C8B 176.2(10) . . . . ?
C1B N1B C5B N2B 178.1(11) . . . . ?
C1B N1B C5B C4B -2.7(18) . . . . ?
C1B C2B C3B C4B -1(2) . . . . ?
C13B N3B C7B C8B -91.9(13) . . . . ?
C13B N3B C7B C6B 83.8(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_chemical_properties_physical    Heat-sensitive
