#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:51:24 +0100 (Tue 04 de Mar de 2025) $
#$Revision: 298216 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/98/7249891.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_7249891
loop_
_publ_author_name
'Dwivedi, Astha M.'
'Gonnade, Rajesh G.'
'Sahoo, Suban K.'
'Bedekar, Ashutosh V.'
_publ_section_title
;
 Separation of isomers of chiral thiourea derivatives via spontaneous
 resolution and rationale of molecular recognition
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1240
_journal_page_last               1247
_journal_paper_doi               10.1039/D4CE01226G
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H20 N2 S'
_chemical_formula_sum            'C17 H20 N2 S'
_chemical_formula_weight         284.41
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-14 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.2178(2)
_cell_length_b                   10.2178(2)
_cell_length_c                   13.0003(4)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.26
_cell_measurement_theta_min      5.00
_cell_volume                     1175.44(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36394
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.820
_diffrn_reflns_theta_min         4.998
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.010(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0318
_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/[σ²(Fo²)+(0.0177P)²+0.3307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                3036
_reflns_number_total             3228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01226g2.cif
_cod_data_source_block           cu_AD_05_11_Cu_0m_a
_cod_depositor_comments
'Adding full bibliography for 7249891--7249892.cif.'
_cod_original_cell_volume        1175.43(6)
_cod_database_code               7249891
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.792
_shelx_estimated_absorpt_t_max   0.918
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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
S1 S 0.11727(6) 0.47033(6) 0.63127(4) 0.02565(14) Uani 1 1 d . . . . .
N1 N 0.3107(2) 0.6732(2) 0.49524(15) 0.0247(4) Uani 1 1 d . . . . .
H1N H 0.372(3) 0.689(3) 0.449(2) 0.013(6) Uiso 1 1 d . . . . .
N2 N 0.2839(2) 0.4411(2) 0.48499(15) 0.0234(4) Uani 1 1 d . . . . .
H2N H 0.346(3) 0.479(3) 0.435(2) 0.032(8) Uiso 1 1 d . . . . .
C1 C 0.2766(3) 0.7927(3) 0.51991(18) 0.0261(5) Uani 1 1 d . . . . .
H1 H 0.208443 0.760420 0.581276 0.031 Uiso 1 1 calc R U . . .
C2 C 0.1942(3) 0.8144(2) 0.43007(17) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.2702(3) 0.8800(3) 0.33899(19) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.374268 0.910632 0.332743 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1957(3) 0.9012(3) 0.25730(19) 0.0348(6) Uani 1 1 d . . . . .
H4 H 0.248549 0.945278 0.195225 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0452(3) 0.8584(3) 0.2658(2) 0.0366(6) Uani 1 1 d . . . . .
H5 H -0.005027 0.874867 0.210138 0.044 Uiso 1 1 calc R U . . .
C6 C -0.0330(3) 0.7915(3) 0.3556(2) 0.0361(6) Uani 1 1 d . . . . .
H6 H -0.137273 0.760503 0.361227 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0424(3) 0.7701(3) 0.4373(2) 0.0282(5) Uani 1 1 d . . . . .
H7 H -0.011094 0.724407 0.498946 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4230(4) 0.9366(3) 0.5474(2) 0.0420(7) Uani 1 1 d . . . . .
H8A H 0.496478 0.961631 0.491764 0.063 Uiso 1 1 calc R U . . .
H8B H 0.463976 0.920645 0.611289 0.063 Uiso 1 1 calc R U . . .
H8C H 0.402469 1.019813 0.556758 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2437(2) 0.5326(2) 0.53194(16) 0.0205(4) Uani 1 1 d . . . . .
C10 C 0.2396(3) 0.2867(3) 0.51488(17) 0.0232(5) Uani 1 1 d . . . . .
H10 H 0.138259 0.240573 0.548720 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3499(3) 0.2796(3) 0.58946(17) 0.0235(5) Uani 1 1 d . . . . .
C12 C 0.2971(3) 0.1917(3) 0.67757(19) 0.0325(6) Uani 1 1 d . . . . .
H12 H 0.192283 0.142193 0.693298 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3950(3) 0.1750(3) 0.7431(2) 0.0400(7) Uani 1 1 d . . . . .
H13 H 0.357006 0.113335 0.802622 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5477(3) 0.2481(3) 0.7215(2) 0.0355(6) Uani 1 1 d . . . . .
H14 H 0.614993 0.236183 0.765817 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6024(3) 0.3384(3) 0.6352(2) 0.0348(6) Uani 1 1 d . . . . .
H15 H 0.707644 0.390023 0.620808 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5042(3) 0.3541(3) 0.56967(19) 0.0294(5) Uani 1 1 d . . . . .
H16 H 0.542753 0.416509 0.510495 0.035 Uiso 1 1 calc R U . . .
C17 C 0.2249(3) 0.1979(3) 0.41703(19) 0.0293(5) Uani 1 1 d . . . . .
H17A H 0.149944 0.200706 0.371417 0.044 Uiso 1 1 calc R U . . .
H17B H 0.192389 0.092825 0.434839 0.044 Uiso 1 1 calc R U . . .
H17C H 0.322825 0.243165 0.381971 0.044 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C9 N1 C1 127.8(2) . . ?
C9 N1 H1N 114.1(17) . . ?
C1 N1 H1N 117.7(17) . . ?
C9 N2 C10 126.47(19) . . ?
C9 N2 H2N 116(2) . . ?
C10 N2 H2N 117(2) . . ?
N1 C1 C2 109.51(18) . . ?
N1 C1 C8 109.1(2) . . ?
C2 C1 C8 112.8(2) . . ?
N1 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
C8 C1 H1 108.4 . . ?
C7 C2 C3 118.7(2) . . ?
C7 C2 C1 120.8(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 N2 114.7(2) . . ?
N1 C9 S1 123.84(18) . . ?
N2 C9 S1 121.50(17) . . ?
N2 C10 C11 112.70(19) . . ?
N2 C10 C17 107.81(19) . . ?
C11 C10 C17 111.07(19) . . ?
N2 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
C17 C10 H10 108.4 . . ?
C12 C11 C16 118.4(2) . . ?
C12 C11 C10 120.1(2) . . ?
C16 C11 C10 121.5(2) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
S1 C9 1.709(2) . ?
N1 C9 1.333(3) . ?
N1 C1 1.463(3) . ?
N1 H1N 0.83(3) . ?
N2 C9 1.342(3) . ?
N2 C10 1.459(3) . ?
N2 H2N 0.85(3) . ?
C1 C2 1.519(3) . ?
C1 C8 1.525(4) . ?
C1 H1 1.0000 . ?
C2 C7 1.385(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.516(3) . ?
C10 C17 1.526(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.388(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
C9 N1 C1 C2 -105.9(3) . . . . ?
C9 N1 C1 C8 130.2(3) . . . . ?
N1 C1 C2 C7 109.2(2) . . . . ?
C8 C1 C2 C7 -129.1(3) . . . . ?
N1 C1 C2 C3 -71.1(3) . . . . ?
C8 C1 C2 C3 50.6(3) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C1 C2 C7 C6 179.2(2) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C1 N1 C9 N2 171.1(2) . . . . ?
C1 N1 C9 S1 -9.4(3) . . . . ?
C10 N2 C9 N1 174.0(2) . . . . ?
C10 N2 C9 S1 -5.5(3) . . . . ?
C9 N2 C10 C11 -90.6(3) . . . . ?
C9 N2 C10 C17 146.5(2) . . . . ?
N2 C10 C11 C12 132.2(2) . . . . ?
C17 C10 C11 C12 -106.7(2) . . . . ?
N2 C10 C11 C16 -50.8(3) . . . . ?
C17 C10 C11 C16 70.3(3) . . . . ?
C16 C11 C12 C13 -1.7(4) . . . . ?
C10 C11 C12 C13 175.3(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C12 C11 C16 C15 1.3(4) . . . . ?
C10 C11 C16 C15 -175.7(2) . . . . ?
