Single-crystal to single-crystal conformational polymorphic transformation in tolbutamide at 313 K. Relation to other polymorphic transformations in tolbutamide and chlorpropamide
Drebushchak, T. N.; Drebushchak, V. A.; Pankrushina, N. A.; Boldyreva, E. V.; CrystEngComm 18 (2016) 5736–; doi:10.1039/C6CE00764C

data_7225538
_publ_section_title
;
 Single-crystal to single-crystal conformational polymorphic
 transformation in tolbutamide at 313 K. Relation to other polymorphic
 transformations in tolbutamide and chlorpropamide
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              5736
_journal_paper_doi               10.1039/C6CE00764C
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C12 H18 N2 O3 S'
_chemical_formula_sum            'C12 H18 N2 O3 S'
_chemical_formula_weight         270.34
_chemical_name_common            'Tolbutamide form I^L^'
_chemical_name_systematic        N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-03-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4331(3)
_cell_length_b                   7.8010(1)
_cell_length_c                   9.0277(1)
_cell_measurement_reflns_used    28126
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.1508
_cell_measurement_theta_min      3.3422
_cell_volume                     1368.58(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_molecular_graphics
;
 ORTEP-3 for Windows (Farrugia, 1997) 
;
_computing_publication_material
;
 SHELXL-2014/6 (Sheldrick, 2014), WinGX (Farrugia, 
 1999), Mercury (Macrae et al., 2008)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47528
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_min         3.349
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'from solution of tolbutamide in ethyl acetate'
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         6600
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0504P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6147
_reflns_number_total             6600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00764c2.cif
_cod_data_source_block           TB-IL_100
_cod_depositor_comments
'Adding full bibliography for 7225535--7225539.cif.'
_cod_database_code               7225538
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2014/6
_shelx_res_checksum              2096