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_7233213
_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_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_name_common            'tenoxicam chloroform I solvate'
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.076(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6019(12)
_cell_length_b                   12.7810(10)
_cell_length_c                   28.841(2)
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.3050
_cell_measurement_theta_min      3.4580
_cell_volume                     3905.5(6)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00   2.00   1.00   60.00    --  -11.27 127.00  94.42   72
  2  \w    -20.00  54.00   1.00   60.00    --   11.43  77.00 150.00   74
  3  \w    -18.00  58.00   1.00   60.00    --   11.43  57.00 -90.00   76
  4  \w    -58.00  41.00   1.00   60.00    --   11.43 -57.00-120.00   99
  5  \w    -61.00  41.00   1.00   60.00    --   11.43 -57.00  90.00  102
  6  \w    -65.00  45.00   1.00   60.00    --   11.43 -77.00   0.00  110
  7  \w    -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       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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
_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_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_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
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.094
_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_restrained_S_all      1.035
_refine_ls_R_factor_all          0.2576
_refine_ls_R_factor_gt           0.1163
_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^)+(0.1678P)^2^+8.2269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3158
_refine_ls_wR_factor_ref         0.3957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2586
_reflns_number_total             6880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00874h2.cif
_cod_data_source_block           tnx_chcl3_I
_cod_depositor_comments
'Adding full bibliography for 7233208--7233213.cif.'
_cod_database_code               7233213
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.816
_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)
;
_shelx_res_checksum              62744
_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
;