The role of S-bond in tenoxicam keto–enolic tautomerization
Arkhipov, Sergey G.; Sherin, Peter S.; Kiryutin, Alexey S.; Lazarenko, Vladimir A.; Tantardini, Christian; CrystEngComm 21 (2019) 5392–; doi:10.1039/C9CE00874H

data_7233209
_publ_section_title
;
 The role of S-bond in tenoxicam keto--enolic tautomerization
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5392
_journal_paper_doi               10.1039/C9CE00874H
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration syn
_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_name_common            'tenoxicam chloroform II solvate'
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2019-07-04 deposited with the CCDC.    2019-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5960(19)
_cell_length_b                   16.740(3)
_cell_length_c                   28.301(6)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      62.03
_cell_measurement_theta_min      3.156
_cell_volume                     4546.2(16)
_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)'
_diffrn_ambient_temperature      100(2)
_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_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
_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_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_description       needle
_exptl_crystal_F_000             2320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform under -18 ?'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.216
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.118
_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_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0636
_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/[\s^2^(Fo^2^)+(0.0875P)^2^+11.7036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1783
_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_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00874h2.cif
_cod_data_source_block           tnx_chcl3_II
_cod_depositor_comments
'Adding full bibliography for 7233208--7233213.cif.'
_cod_database_code               7233209
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.878
_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)
;
_shelx_res_checksum              60541
_olex2_submission_special_instructions 'No special instructions were received'