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#$Date: 2023-01-24 12:24:51 +0200 (Tue, 24 Jan 2023) $
#$Revision: 280556 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106567.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_8106567
loop_
_publ_author_name
'El-Emam, Ali A.'
'Al-Omary, Fatmah A. M.'
'Al-Rasheed, Lamees S.'
'Ghabbour, Hazem A.'
'Al-Abdullah, Ebtehal S.'
_publ_section_title
;
 Crystal structure of
 (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea,
 C24H27ClN2S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              453
_journal_page_last               456
_journal_paper_doi               10.1515/ncrs-2016-0315
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C24 H27 Cl N2 S'
_chemical_formula_weight         410.99
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                109.605(2)
_cell_angle_beta                 96.515(2)
_cell_angle_gamma                97.312(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1670(3)
_cell_length_b                   12.2734(6)
_cell_length_c                   13.1560(6)
_cell_measurement_reflns_used    9393
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.85
_cell_volume                     1066.08(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18387
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9078
_exptl_absorpt_correction_T_min  0.8806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0604P)²+0.4331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                3483
_reflns_number_total             4883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0315_suppl.cif
_cod_data_source_block           a_a
_cod_original_cell_volume        1066.08(8)
_cod_database_code               8106567
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.35386(12) 0.25966(7) 0.81108(8) 0.0840(3) Uani 1 1 d . . .
S1 S 0.74453(7) 0.64574(5) 0.76585(5) 0.04242(17) Uani 1 1 d . . .
N1 N 0.5284(2) 0.71345(15) 0.63081(14) 0.0363(4) Uani 1 1 d . . .
N2 N 0.3577(2) 0.64492(16) 0.74092(14) 0.0412(4) Uani 1 1 d . . .
C1 C 0.4607(3) 0.7930(2) 0.48916(19) 0.0474(5) Uani 1 1 d . . .
H1A H 0.5428 0.7427 0.4462 0.057 Uiso 1 1 calc R . .
H1B H 0.5417 0.8689 0.5359 0.057 Uiso 1 1 calc R . .
C2 C 0.3050(3) 0.8142(2) 0.4111(2) 0.0539(6) Uani 1 1 d . . .
H2A H 0.3659 0.8528 0.3642 0.065 Uiso 1 1 calc R . .
C3 C 0.1829(4) 0.6971(2) 0.33911(19) 0.0582(7) Uani 1 1 d . . .
H3A H 0.0820 0.7101 0.2887 0.070 Uiso 1 1 calc R . .
H3B H 0.2628 0.6465 0.2946 0.070 Uiso 1 1 calc R . .
C4 C 0.0929(3) 0.6370(2) 0.4092(2) 0.0521(6) Uani 1 1 d . . .
H4A H 0.0128 0.5601 0.3612 0.062 Uiso 1 1 calc R . .
C5 C 0.2475(3) 0.61608(18) 0.48742(18) 0.0427(5) Uani 1 1 d . . .
H5A H 0.1873 0.5764 0.5328 0.051 Uiso 1 1 calc R . .
H5B H 0.3285 0.5645 0.4449 0.051 Uiso 1 1 calc R . .
C6 C 0.3703(3) 0.73327(16) 0.56108(15) 0.0327(4) Uani 1 1 d . . .
C7 C 0.2463(3) 0.8132(2) 0.62741(18) 0.0493(6) Uani 1 1 d . . .
H7A H 0.3258 0.8897 0.6740 0.059 Uiso 1 1 calc R . .
H7B H 0.1882 0.7766 0.6756 0.059 Uiso 1 1 calc R . .
C8 C 0.0886(4) 0.8323(2) 0.5487(2) 0.0598(7) Uani 1 1 d . . .
H8A H 0.0052 0.8829 0.5919 0.072 Uiso 1 1 calc R . .
C9 C -0.0311(3) 0.7146(3) 0.4759(2) 0.0614(7) Uani 1 1 d . . .
H9A H -0.0911 0.6754 0.5217 0.074 Uiso 1 1 calc R . .
H9B H -0.1339 0.7271 0.4263 0.074 Uiso 1 1 calc R . .
C10 C 0.1821(4) 0.8939(2) 0.4782(2) 0.0653(7) Uani 1 1 d . . .
H10A H 0.0826 0.9096 0.4289 0.078 Uiso 1 1 calc R . .
H10B H 0.2621 0.9699 0.5257 0.078 Uiso 1 1 calc R . .
C11 C 0.5148(3) 0.66702(16) 0.70927(15) 0.0337(4) Uani 1 1 d . . .
C12 C 0.7813(3) 0.76904(19) 0.89527(17) 0.0443(5) Uani 1 1 d . . .
H12A H 0.6744 0.7595 0.9348 0.053 Uiso 1 1 calc R . .
H12B H 0.9005 0.7686 0.9411 0.053 Uiso 1 1 calc R . .
C13 C 0.7939(3) 0.88483(18) 0.87905(16) 0.0431(5) Uani 1 1 d . . .
C14 C 0.9561(5) 0.9309(2) 0.8505(2) 0.0732(8) Uani 1 1 d . . .
H14A H 1.0618 0.8911 0.8435 0.088 Uiso 1 1 calc R . .
C15 C 0.9643(8) 1.0352(3) 0.8322(3) 0.1201(19) Uani 1 1 d . . .
H15A H 1.0755 1.0660 0.8109 0.144 Uiso 1 1 calc R . .
C16 C 0.8166(11) 1.0949(3) 0.8442(3) 0.136(3) Uani 1 1 d . . .
H16A H 0.8257 1.1678 0.8330 0.164 Uiso 1 1 calc R . .
C17 C 0.6540(8) 1.0492(3) 0.8724(3) 0.1100(15) Uani 1 1 d . . .
H17A H 0.5490 1.0896 0.8794 0.132 Uiso 1 1 calc R . .
C18 C 0.6432(4) 0.9439(2) 0.8905(2) 0.0685(7) Uani 1 1 d . . .
H18A H 0.5313 0.9126 0.9109 0.082 Uiso 1 1 calc R . .
C19 C 0.3344(3) 0.58260(19) 0.81193(17) 0.0384(5) Uani 1 1 d . . .
C20 C 0.3618(3) 0.4667(2) 0.78347(18) 0.0435(5) Uani 1 1 d . . .
H20A H 0.4082 0.4299 0.7178 0.052 Uiso 1 1 calc R . .
C21 C 0.3212(3) 0.4058(2) 0.8511(2) 0.0508(6) Uani 1 1 d . . .
C22 C 0.2558(4) 0.4555(3) 0.9473(2) 0.0631(7) Uani 1 1 d . . .
H22A H 0.2294 0.4119 0.9931 0.076 Uiso 1 1 calc R . .
C23 C 0.2298(4) 0.5701(3) 0.9752(2) 0.0638(7) Uani 1 1 d . . .
H23A H 0.1858 0.6065 1.0419 0.077 Uiso 1 1 calc R . .
C24 C 0.2662(3) 0.6337(2) 0.9084(2) 0.0511(6) Uani 1 1 d . . .
H24A H 0.2446 0.7124 0.9284 0.061 Uiso 1 1 calc R . .
H1N1 H 0.642(3) 0.7350(19) 0.6208(17) 0.039(6) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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'
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
C11 S1 C12 97.44(9) . .
C11 N1 C6 127.04(17) . .
C11 N1 H1N1 116.5(14) . .
C6 N1 H1N1 116.5(14) . .
C11 N2 C19 123.64(16) . .
C6 C1 C2 110.24(17) . .
C6 C1 H1A 109.6 . .
C2 C1 H1A 109.6 . .
C6 C1 H1B 109.6 . .
C2 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
C3 C2 C10 110.0(2) . .
C3 C2 C1 109.17(19) . .
C10 C2 C1 109.1(2) . .
C3 C2 H2A 109.5 . .
C10 C2 H2A 109.5 . .
C1 C2 H2A 109.5 . .
C4 C3 C2 109.96(19) . .
C4 C3 H3A 109.7 . .
C2 C3 H3A 109.7 . .
C4 C3 H3B 109.7 . .
C2 C3 H3B 109.7 . .
H3A C3 H3B 108.2 . .
C3 C4 C9 109.3(2) . .
C3 C4 C5 110.26(19) . .
C9 C4 C5 108.82(19) . .
C3 C4 H4A 109.5 . .
C9 C4 H4A 109.5 . .
C5 C4 H4A 109.5 . .
C6 C5 C4 109.77(17) . .
C6 C5 H5A 109.7 . .
C4 C5 H5A 109.7 . .
C6 C5 H5B 109.7 . .
C4 C5 H5B 109.7 . .
H5A C5 H5B 108.2 . .
N1 C6 C5 110.19(15) . .
N1 C6 C1 106.68(15) . .
C5 C6 C1 108.70(17) . .
N1 C6 C7 112.57(16) . .
C5 C6 C7 109.99(17) . .
C1 C6 C7 108.57(17) . .
C6 C7 C8 109.30(17) . .
C6 C7 H7A 109.8 . .
C8 C7 H7A 109.8 . .
C6 C7 H7B 109.8 . .
C8 C7 H7B 109.8 . .
H7A C7 H7B 108.3 . .
C9 C8 C10 110.0(2) . .
C9 C8 C7 109.7(2) . .
C10 C8 C7 108.8(2) . .
C9 C8 H8A 109.4 . .
C10 C8 H8A 109.4 . .
C7 C8 H8A 109.4 . .
C4 C9 C8 110.1(2) . .
C4 C9 H9A 109.6 . .
C8 C9 H9A 109.6 . .
C4 C9 H9B 109.6 . .
C8 C9 H9B 109.6 . .
H9A C9 H9B 108.2 . .
C2 C10 C8 108.56(19) . .
C2 C10 H10A 110.0 . .
C8 C10 H10A 110.0 . .
C2 C10 H10B 110.0 . .
C8 C10 H10B 110.0 . .
H10A C10 H10B 108.4 . .
N2 C11 N1 122.56(17) . .
N2 C11 S1 125.22(15) . .
N1 C11 S1 112.19(14) . .
C13 C12 S1 112.16(14) . .
C13 C12 H12A 109.2 . .
S1 C12 H12A 109.2 . .
C13 C12 H12B 109.2 . .
S1 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C18 C13 C14 119.8(3) . .
C18 C13 C12 120.4(2) . .
C14 C13 C12 119.8(2) . .
C13 C14 C15 119.5(4) . .
C13 C14 H14A 120.2 . .
C15 C14 H14A 120.2 . .
C16 C15 C14 121.2(4) . .
C16 C15 H15A 119.4 . .
C14 C15 H15A 119.4 . .
C15 C16 C17 119.6(3) . .
C15 C16 H16A 120.2 . .
C17 C16 H16A 120.2 . .
C16 C17 C18 119.9(4) . .
C16 C17 H17A 120.1 . .
C18 C17 H17A 120.1 . .
C13 C18 C17 120.0(4) . .
C13 C18 H18A 120.0 . .
C17 C18 H18A 120.0 . .
C24 C19 C20 118.9(2) . .
C24 C19 N2 119.47(19) . .
C20 C19 N2 121.39(19) . .
C21 C20 C19 119.4(2) . .
C21 C20 H20A 120.3 . .
C19 C20 H20A 120.3 . .
C22 C21 C20 122.4(2) . .
C22 C21 Cl1 119.70(19) . .
C20 C21 Cl1 117.9(2) . .
C21 C22 C23 118.0(2) . .
C21 C22 H22A 121.0 . .
C23 C22 H22A 121.0 . .
C22 C23 C24 121.3(2) . .
C22 C23 H23A 119.3 . .
C24 C23 H23A 119.3 . .
C23 C24 C19 120.0(2) . .
C23 C24 H24A 120.0 . .
C19 C24 H24A 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C21 1.747(2) .
S1 C11 1.8155(19) .
S1 C12 1.824(2) .
N1 C11 1.343(3) .
N1 C6 1.473(2) .
N1 H1N1 0.86(2) .
N2 C11 1.272(3) .
N2 C19 1.403(2) .
C1 C6 1.528(3) .
C1 C2 1.536(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.518(4) .
C2 C10 1.526(4) .
C2 H2A 1.0000 .
C3 C4 1.510(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C9 1.516(3) .
C4 C5 1.531(3) .
C4 H4A 1.0000 .
C5 C6 1.527(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.529(3) .
C7 C8 1.540(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.519(4) .
C8 C10 1.537(4) .
C8 H8A 1.0000 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C12 C13 1.500(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C18 1.370(4) .
C13 C14 1.373(4) .
C14 C15 1.375(5) .
C14 H14A 0.9500 .
C15 C16 1.356(7) .
C15 H15A 0.9500 .
C16 C17 1.372(7) .
C16 H16A 0.9500 .
C17 C18 1.385(4) .
C17 H17A 0.9500 .
C18 H18A 0.9500 .
C19 C24 1.388(3) .
C19 C20 1.390(3) .
C20 C21 1.373(3) .
C20 H20A 0.9500 .
C21 C22 1.371(4) .
C22 C23 1.373(4) .
C22 H22A 0.9500 .
C23 C24 1.383(3) .
C23 H23A 0.9500 .
C24 H24A 0.9500 .
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
C6 C1 C2 C3 -59.8(2) . . . .
C6 C1 C2 C10 60.5(3) . . . .
C10 C2 C3 C4 -60.6(2) . . . .
C1 C2 C3 C4 59.2(2) . . . .
C2 C3 C4 C9 60.0(2) . . . .
C2 C3 C4 C5 -59.5(3) . . . .
C3 C4 C5 C6 59.6(2) . . . .
C9 C4 C5 C6 -60.2(2) . . . .
C11 N1 C6 C5 -64.8(2) . . . .
C11 N1 C6 C1 177.42(19) . . . .
C11 N1 C6 C7 58.4(3) . . . .
C4 C5 C6 N1 -175.67(16) . . . .
C4 C5 C6 C1 -59.1(2) . . . .
C4 C5 C6 C7 59.7(2) . . . .
C2 C1 C6 N1 178.52(18) . . . .
C2 C1 C6 C5 59.7(2) . . . .
C2 C1 C6 C7 -59.9(2) . . . .
N1 C6 C7 C8 178.36(18) . . . .
C5 C6 C7 C8 -58.3(2) . . . .
C1 C6 C7 C8 60.5(2) . . . .
C6 C7 C8 C9 58.5(3) . . . .
C6 C7 C8 C10 -61.9(3) . . . .
C3 C4 C9 C8 -59.6(2) . . . .
C5 C4 C9 C8 60.8(3) . . . .
C10 C8 C9 C4 59.4(2) . . . .
C7 C8 C9 C4 -60.3(3) . . . .
C3 C2 C10 C8 59.0(3) . . . .
C1 C2 C10 C8 -60.7(3) . . . .
C9 C8 C10 C2 -58.5(3) . . . .
C7 C8 C10 C2 61.7(3) . . . .
C19 N2 C11 N1 171.30(19) . . . .
C19 N2 C11 S1 -11.0(3) . . . .
C6 N1 C11 N2 -7.6(3) . . . .
C6 N1 C11 S1 174.46(14) . . . .
C12 S1 C11 N2 -73.01(19) . . . .
C12 S1 C11 N1 104.87(15) . . . .
C11 S1 C12 C13 -62.60(17) . . . .
S1 C12 C13 C18 104.2(2) . . . .
S1 C12 C13 C14 -74.6(2) . . . .
C18 C13 C14 C15 -0.9(4) . . . .
C12 C13 C14 C15 177.9(2) . . . .
C13 C14 C15 C16 1.4(5) . . . .
C14 C15 C16 C17 -1.6(6) . . . .
C15 C16 C17 C18 1.3(6) . . . .
C14 C13 C18 C17 0.6(4) . . . .
C12 C13 C18 C17 -178.2(2) . . . .
C16 C17 C18 C13 -0.8(5) . . . .
C11 N2 C19 C24 123.8(2) . . . .
C11 N2 C19 C20 -61.9(3) . . . .
C24 C19 C20 C21 -0.1(3) . . . .
N2 C19 C20 C21 -174.31(19) . . . .
C19 C20 C21 C22 -0.7(3) . . . .
C19 C20 C21 Cl1 178.91(16) . . . .
C20 C21 C22 C23 0.4(4) . . . .
Cl1 C21 C22 C23 -179.2(2) . . . .
C21 C22 C23 C24 0.6(4) . . . .
C22 C23 C24 C19 -1.4(4) . . . .
C20 C19 C24 C23 1.1(3) . . . .
N2 C19 C24 C23 175.4(2) . . . .
