#------------------------------------------------------------------------------
#$Date: 2023-11-11 01:08:25 +0200 (Sat, 11 Nov 2023) $
#$Revision: 287522 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132322.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_7132322
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            'C11.07 H15.66 Cl0.47 N2 O3 S'
_chemical_formula_weight         273.35
_chemical_name_common            'Chloropropamide Tolbutamide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_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            8
_cell_length_a                   15.1745(11)
_cell_length_b                   9.3155(5)
_cell_length_c                   19.5240(12)
_cell_measurement_reflns_used    543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      2
_cell_volume                     2759.9(3)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0590
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33581
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_min         2.481
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       0.039(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0937
_refine_ls_shift/su_max          4.541
_refine_ls_shift/su_mean         0.112
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1449P)²+2.4113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2588
_refine_ls_wR_factor_ref         0.3051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1562
_reflns_number_total             2530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04725c2.cif
_cod_data_source_block           SS2_46
_cod_database_code               7132322
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
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
Cl1 Cl 0.1820(4) 0.0226(6) 0.91517(16) 0.170(3) Uani 0.469(14) 1 d . . P A 1
C1 C 0.1820(4) 0.0226(6) 0.91517(16) 0.170(3) Uani 0.531(14) 1 d . . P A 2
H1A H 0.1283 0.0219 0.9412 0.256 Uiso 0.531(14) 1 calc R U P A 2
H1B H 0.2216 0.0924 0.9341 0.256 Uiso 0.531(14) 1 calc R U P A 2
H1C H 0.2088 -0.0706 0.9170 0.256 Uiso 0.531(14) 1 calc R U P A 2
C2 C 0.1595(5) 0.0654(10) 0.8327(3) 0.112(2) Uani 1 1 d . . . . .
C3 C 0.1432(7) 0.1993(10) 0.8134(5) 0.148(3) Uani 1 1 d . . . . .
H3 H 0.1432 0.2717 0.8462 0.177 Uiso 1 1 calc R U . . .
C4 C 0.1261(7) 0.2348(8) 0.7448(4) 0.140(3) Uani 1 1 d . . . . .
H4 H 0.1147 0.3295 0.7326 0.169 Uiso 1 1 calc R U . . .
C5 C 0.1260(4) 0.1319(6) 0.6972(3) 0.0835(15) Uani 1 1 d . . . . .
C6 C 0.1408(6) -0.0047(8) 0.7173(3) 0.130(3) Uani 1 1 d . . . . .
H6 H 0.1410 -0.0777 0.6848 0.156 Uiso 1 1 calc R U . . .
C7 C 0.1555(7) -0.0378(9) 0.7846(4) 0.153(4) Uani 1 1 d . . . . .
H7 H 0.1628 -0.1333 0.7973 0.184 Uiso 1 1 calc R U . . .
S8 S 0.10312(11) 0.17254(15) 0.61095(8) 0.0893(7) Uani 1 1 d . . . . .
N9 N 0.1943(3) 0.2382(4) 0.5800(2) 0.0872(14) Uani 1 1 d . . . . .
H9 H 0.1943 0.3262 0.5666 0.105 Uiso 1 1 calc R U . . .
C10 C 0.2721(4) 0.1599(5) 0.5741(2) 0.0788(15) Uani 1 1 d . . . . .
N11 N 0.3426(4) 0.2389(5) 0.5605(2) 0.0937(16) Uani 1 1 d . . . . .
H11 H 0.3362 0.3303 0.5567 0.112 Uiso 1 1 calc R U . . .
C12 C 0.4297(5) 0.1786(8) 0.5516(4) 0.116(2) Uani 1 1 d . . . . .
H12A H 0.4618 0.2348 0.5180 0.139 Uiso 1 1 calc R U . . .
H12B H 0.4245 0.0814 0.5343 0.139 Uiso 1 1 calc R U . . .
C13 C 0.4808(7) 0.1766(10) 0.6177(7) 0.177(5) Uani 1 1 d . . . . .
H13A H 0.4853 0.2738 0.6351 0.213 Uiso 1 1 calc R U . . .
H13B H 0.4486 0.1202 0.6512 0.213 Uiso 1 1 calc R U . . .
C14 C 0.5683(9) 0.1176(14) 0.6103(9) 0.217(7) Uani 1 1 d . . . . .
H14A H 0.6080 0.1843 0.5878 0.260 Uiso 1 1 calc R U . A 2
H14B H 0.5679 0.0273 0.5856 0.260 Uiso 1 1 calc R U . A 2
C15 C 0.5914(11) 0.097(2) 0.6853(10) 0.152(11) Uani 0.531(14) 1 d . U P A 2
H15A H 0.5419 0.1241 0.7132 0.228 Uiso 0.531(14) 1 calc R U P A 2
H15B H 0.6411 0.1563 0.6967 0.228 Uiso 0.531(14) 1 calc R U P A 2
H15C H 0.6057 -0.0017 0.6935 0.228 Uiso 0.531(14) 1 calc R U P A 2
O3 O 0.0434(3) 0.2904(5) 0.6090(3) 0.1189(16) Uani 1 1 d . . . . .
O2 O 0.0814(3) 0.0431(4) 0.5763(2) 0.1030(14) Uani 1 1 d . . . . .
O4 O 0.2718(3) 0.0306(4) 0.5808(2) 0.0985(14) Uani 1 1 d . . . . .
H15 H 0.5914(11) 0.097(2) 0.6853(10) 0.3(2) Uiso 0.469(14) 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'
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'
Cl Cl 0.1484 0.1585 '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
C3 C2 C7 117.7(7) . . ?
C3 C2 Cl1 122.0(6) . . ?
C7 C2 Cl1 120.3(7) . . ?
C2 C3 C4 121.9(7) . . ?
C5 C4 C3 119.6(7) . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 S8 120.7(5) . . ?
C6 C5 S8 120.9(4) . . ?
C5 C6 C7 121.2(7) . . ?
C2 C7 C6 121.1(8) . . ?
O2 S8 O3 119.6(3) . . ?
O2 S8 N9 109.8(3) . . ?
O3 S8 N9 103.9(3) . . ?
O2 S8 C5 108.6(3) . . ?
O3 S8 C5 108.5(3) . . ?
N9 S8 C5 105.5(3) . . ?
C10 N9 S8 123.6(3) . . ?
O4 C10 N11 125.2(6) . . ?
O4 C10 N9 120.6(5) . . ?
N11 C10 N9 114.2(4) . . ?
C10 N11 C12 123.1(5) . . ?
N11 C12 C13 111.9(7) . . ?
C14 C13 C12 113.1(11) . . ?
C13 C14 C15 99.4(13) . . ?
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
Cl1 C2 1.693(8) . ?
C2 C3 1.326(11) . ?
C2 C7 1.346(10) . ?
C3 C4 1.403(12) . ?
C4 C5 1.335(8) . ?
C5 C6 1.350(9) . ?
C5 S8 1.762(6) . ?
C6 C7 1.367(9) . ?
S8 O2 1.421(4) . ?
S8 O3 1.424(4) . ?
S8 N9 1.629(5) . ?
N9 C10 1.394(7) . ?
C10 O4 1.211(6) . ?
C10 N11 1.325(7) . ?
N11 C12 1.447(8) . ?
C12 C13 1.505(13) . ?
C13 C14 1.445(15) . ?
C14 C15 1.518(19) . ?
