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_7233211
_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         'C13 H11 N3 O4 S2, C3 H7 N O'
_chemical_formula_sum            'C16 H18 N4 O5 S2'
_chemical_formula_weight         410.46
_chemical_name_common            'tenoxicam dimethylformamide solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_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                74.530(4)
_cell_angle_beta                 77.500(4)
_cell_angle_gamma                85.545(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1060(4)
_cell_length_b                   9.4381(4)
_cell_length_c                   11.6586(6)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1190
_cell_measurement_theta_min      1.8380
_cell_volume                     942.58(8)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -40.00  22.00   1.00   50.00    --  -23.36 -57.00  30.00   62
  2  \w    -43.00  68.00   1.00   50.00    --  -23.36  37.00-120.00  111
  3  \w    -31.00  28.00   1.00   50.00    --   22.89  96.00 -51.00   59
  4  \w     73.00 112.00   1.00   50.00    --   22.89-178.00 -90.00   39
  5  \w    -44.00  76.00   1.00   50.00    --  -23.36  77.00  60.00  120
  6  \w    -80.00  29.00   1.00   50.00    --  -23.36 -37.00 120.00  109
  7  \w    -77.00  29.00   1.00   50.00    --  -23.36  96.00 -51.00  106
  8  \w   -122.00 -84.00   1.00   50.00    --  -23.36 -37.00 120.00   38
  9  \w   -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       '\w 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_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_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_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_description       block
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMFA'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.042
_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_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0586P)^2^+0.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2958
_reflns_number_total             3857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00874h2.cif
_cod_data_source_block           tnx_dmfa
_cod_depositor_comments
'Adding full bibliography for 7233208--7233213.cif.'
_cod_original_cell_volume        942.56(8)
_cod_database_code               7233211
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.870
_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)
;
_shelx_res_checksum              18611
_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