#------------------------------------------------------------------------------
#$Date: 2023-11-11 01:08:25 +0200 (Sat, 11 Nov 2023) $
#$Revision: 287522 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132317.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7132317
loop_
_publ_author_name
'Spoletti, Enrico'
'Verma, Vivek'
'Cappuccino, Chiara'
'Lusi, Matteo'
_publ_section_title
;
 Solid Solution Polymorphs afford two High-Soluble Co-Drug Forms of
 Tolbutamide and Chlorpropamide
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04725C
_journal_year                    2023
_chemical_formula_sum            'C10.91 H15.28 Cl0.54 N2 O3 S'
_chemical_formula_weight         273.86
_chemical_name_common            'Chloropropamide Tolbutamide'
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1171(17)
_cell_length_b                   7.5762(7)
_cell_length_c                   9.1129(7)
_cell_measurement_reflns_used    342
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      4
_cell_volume                     1388.9(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.427
_diffrn_reflns_theta_min         2.873
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 948 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0341
_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)+(0.0477P)²+0.2142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2218
_reflns_number_total             2549
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04725c2.cif
_cod_data_source_block           SS1_54
_cod_database_code               7132317
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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
S01 S 0.39664(4) 0.33756(12) 0.46500(9) 0.0577(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2354(3) 1.0306(7) 0.5804(7) 0.117(2) Uani 0.544(10) 1 d D . P A 1
O3 O 0.40527(13) 0.2434(4) 0.5986(3) 0.0695(7) Uani 1 1 d . . . . .
O1 O 0.50276(14) 0.5356(4) 0.6134(3) 0.0761(8) Uani 1 1 d . . . . .
O2 O 0.36696(15) 0.2492(4) 0.3433(3) 0.0695(8) Uani 1 1 d . . . . .
N2 N 0.54875(16) 0.6189(4) 0.3975(3) 0.0622(8) Uani 1 1 d . . . . .
H2 H 0.5514 0.5975 0.3050 0.075 Uiso 1 1 calc R U . . .
N1 N 0.46830(15) 0.4046(5) 0.4020(3) 0.0591(8) Uani 1 1 d . . . . .
C8 C 0.50774(16) 0.5240(5) 0.4788(3) 0.0567(8) Uani 1 1 d . . . . .
C5 C 0.35237(18) 0.5329(6) 0.5024(3) 0.0595(9) Uani 1 1 d . . . . .
C9 C 0.58944(19) 0.7587(5) 0.4600(5) 0.0710(10) Uani 1 1 d . . . . .
H9A H 0.6291 0.7726 0.4007 0.085 Uiso 1 1 calc R U . . .
H9B H 0.6033 0.7238 0.5577 0.085 Uiso 1 1 calc R U . . .
C6 C 0.3560(2) 0.6740(6) 0.4074(5) 0.0754(12) Uani 1 1 d . . . . .
H6 H 0.3823 0.6661 0.3237 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3212(3) 0.8264(6) 0.4352(6) 0.0838(13) Uani 1 1 d . . . . .
H7 H 0.3238 0.9215 0.3709 0.101 Uiso 1 1 calc R U . . .
C2 C 0.2823(2) 0.8367(6) 0.5595(6) 0.0834(13) Uani 1 1 d D . . . .
C4 C 0.3138(2) 0.5430(7) 0.6266(5) 0.0850(13) Uani 1 1 d . . . . .
H4 H 0.3120 0.4488 0.6919 0.102 Uiso 1 1 calc R U . . .
C3 C 0.2781(3) 0.6937(8) 0.6530(6) 0.0986(17) Uani 1 1 d . . . . .
H3 H 0.2506 0.6998 0.7350 0.118 Uiso 1 1 calc R U . . .
C10 C 0.5541(4) 0.9336(7) 0.4693(10) 0.133(2) Uani 1 1 d . . . . .
H10A H 0.5407 0.9701 0.3717 0.159 Uiso 1 1 calc R U . . .
H10B H 0.5144 0.9206 0.5285 0.159 Uiso 1 1 calc R U . . .
C11 C 0.5978(7) 1.0737(11) 0.5357(15) 0.184(5) Uani 1 1 d . . . . .
H11A H 0.5710 1.1538 0.5938 0.221 Uiso 1 1 calc R U . A 2
H11B H 0.6303 1.0191 0.6001 0.221 Uiso 1 1 calc R U . A 2
H1 H 0.4718(19) 0.399(5) 0.315(5) 0.060(11) Uiso 1 1 d . . . . .
C12 C 0.625(2) 1.152(5) 0.445(6) 0.28(3) Uani 0.456(10) 1 d . . P A 2
H12A H 0.5935 1.1879 0.3714 0.426 Uiso 0.456(10) 1 calc R U P A 2
H12B H 0.6582 1.0779 0.4002 0.426 Uiso 0.456(10) 1 calc R U P A 2
H12C H 0.6458 1.2540 0.4864 0.426 Uiso 0.456(10) 1 calc R U P A 2
C1 C 0.2510(11) 1.021(3) 0.647(3) 0.088(6) Uani 0.456(10) 1 d D . P A 2
H1A H 0.2437 1.1134 0.5766 0.132 Uiso 0.456(10) 1 calc R U P A 2
H1B H 0.2823 1.0611 0.7197 0.132 Uiso 0.456(10) 1 calc R U P A 2
H1C H 0.2097 0.9921 0.6941 0.132 Uiso 0.456(10) 1 calc R U P A 2
H11 H 0.620(5) 1.136(18) 0.448(11) 0.05(3) Uiso 0.544(10) 1 d . . P A 1
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'
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 S01 O2 118.78(16) . . ?
O3 S01 N1 110.46(17) . . ?
O2 S01 N1 104.00(16) . . ?
O3 S01 C5 108.55(17) . . ?
O2 S01 C5 109.45(18) . . ?
N1 S01 C5 104.67(18) . . ?
C8 N2 C9 121.8(3) . . ?
C8 N2 H2 119.1 . . ?
C9 N2 H2 119.1 . . ?
C8 N1 S01 121.9(2) . . ?
C8 N1 H1 119(3) . . ?
S01 N1 H1 114(3) . . ?
O1 C8 N2 124.7(3) . . ?
O1 C8 N1 120.0(3) . . ?
N2 C8 N1 115.3(3) . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 S01 119.5(3) . . ?
C6 C5 S01 120.3(3) . . ?
N2 C9 C10 113.4(4) . . ?
N2 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C7 C2 C3 119.9(4) . . ?
C7 C2 C1 129.2(9) . . ?
C3 C2 C1 109.0(9) . . ?
C7 C2 Cl1 116.2(5) . . ?
C3 C2 Cl1 123.7(4) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C11 C10 C9 111.6(6) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 110(3) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C10 C11 H11 105(7) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
S01 O3 1.422(3) . ?
S01 O2 1.426(3) . ?
S01 N1 1.633(3) . ?
S01 C5 1.760(4) . ?
Cl1 C2 1.757(7) . ?
O1 C8 1.234(4) . ?
N2 C8 1.322(4) . ?
N2 C9 1.455(5) . ?
N2 H2 0.8600 . ?
N1 C8 1.392(5) . ?
N1 H1 0.80(4) . ?
C5 C4 1.375(5) . ?
C5 C6 1.378(5) . ?
C9 C10 1.506(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 C7 1.374(6) . ?
C6 H6 0.9300 . ?
C7 C2 1.379(7) . ?
C7 H7 0.9300 . ?
C2 C3 1.381(7) . ?
C2 C1 1.730(18) . ?
C4 C3 1.370(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C10 C11 1.505(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.16(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11 1.03(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
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
O3 S01 N1 C8 -63.2(4) . . . . ?
O2 S01 N1 C8 168.3(3) . . . . ?
C5 S01 N1 C8 53.5(3) . . . . ?
C9 N2 C8 O1 -4.6(6) . . . . ?
C9 N2 C8 N1 175.2(3) . . . . ?
S01 N1 C8 O1 25.5(5) . . . . ?
S01 N1 C8 N2 -154.3(3) . . . . ?
O3 S01 C5 C4 -22.1(4) . . . . ?
O2 S01 C5 C4 108.9(3) . . . . ?
N1 S01 C5 C4 -140.1(3) . . . . ?
O3 S01 C5 C6 158.3(3) . . . . ?
O2 S01 C5 C6 -70.7(4) . . . . ?
N1 S01 C5 C6 40.3(4) . . . . ?
C8 N2 C9 C10 -85.9(6) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
S01 C5 C6 C7 179.5(4) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
C6 C7 C2 C3 -0.9(7) . . . . ?
C6 C7 C2 C1 161.6(10) . . . . ?
C6 C7 C2 Cl1 -176.1(5) . . . . ?
C6 C5 C4 C3 1.3(7) . . . . ?
S01 C5 C4 C3 -178.3(4) . . . . ?
C5 C4 C3 C2 -2.4(8) . . . . ?
C7 C2 C3 C4 2.2(8) . . . . ?
C1 C2 C3 C4 -163.5(9) . . . . ?
Cl1 C2 C3 C4 176.9(5) . . . . ?
N2 C9 C10 C11 179.6(8) . . . . ?
C9 C10 C11 C12 94(3) . . . . ?
