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#$Date: 2023-04-19 12:01:15 +0300 (Wed, 19 Apr 2023) $
#$Revision: 282730 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107086.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_8107086
loop_
_publ_author_name
'Al-Omary, Fatmah A. M.'
'Al-Rasheed, Lamees S.'
'Ghabbour, Hazem A.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of 1-(adamantan-1-yl)-3-(4-bromophenyl)thiourea,
 C17H21BrN2S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1033
_journal_page_last               1035
_journal_paper_doi               10.1515/ncrs-2016-0037
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C17 H21 Br N2 S'
_chemical_formula_weight         365.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0675(7)
_cell_length_b                   8.3422(3)
_cell_length_c                   22.5970(8)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.62
_cell_measurement_theta_min      2.39
_cell_volume                     3217.4(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            94777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.177
_diffrn_reflns_theta_min         2.387
_exptl_absorpt_coefficient_mu    2.680
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.254
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0275P)²+1.8924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4365
_reflns_number_total             6159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0037_suppl.cif
_cod_data_source_block           a_a
_cod_database_code               8107086
_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   0.340
_shelx_estimated_absorpt_t_max   0.549
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
Br1 Br 0.85483(2) 1.08286(2) 0.49890(2) 0.02160(5) Uani 1 1 d . . . . .
S1 S 0.64189(2) 0.83748(4) 0.24363(2) 0.01154(7) Uani 1 1 d . . . . .
N1 N 0.68609(7) 0.53228(15) 0.22343(5) 0.0125(2) Uani 1 1 d . . . . .
N2 N 0.75715(7) 0.66164(14) 0.29236(5) 0.0112(2) Uani 1 1 d . . . . .
C1 C 0.63266(8) 0.48893(16) 0.17477(6) 0.0104(2) Uani 1 1 d . . . . .
C2 C 0.64562(9) 0.30820(17) 0.16505(6) 0.0138(3) Uani 1 1 d . . . . .
H2A H 0.7014 0.2882 0.1554 0.017 Uiso 1 1 calc R U . . .
H2B H 0.6330 0.2494 0.2019 0.017 Uiso 1 1 calc R U . . .
C3 C 0.59395(9) 0.24645(17) 0.11465(6) 0.0140(3) Uani 1 1 d . . . . .
H3A H 0.6031 0.1291 0.1090 0.017 Uiso 1 1 calc R U . . .
C4 C 0.50768(9) 0.27545(18) 0.13038(7) 0.0160(3) Uani 1 1 d . . . . .
H4A H 0.4737 0.2366 0.0979 0.019 Uiso 1 1 calc R U . . .
H4B H 0.4940 0.2157 0.1668 0.019 Uiso 1 1 calc R U . . .
C5 C 0.49436(9) 0.45499(18) 0.14001(6) 0.0143(3) Uani 1 1 d . . . . .
H5A H 0.4381 0.4740 0.1501 0.017 Uiso 1 1 calc R U . . .
C7 C 0.65316(8) 0.57777(17) 0.11726(6) 0.0128(3) Uani 1 1 d . . . . .
H7A H 0.7089 0.5594 0.1072 0.015 Uiso 1 1 calc R U . . .
H7B H 0.6452 0.6944 0.1226 0.015 Uiso 1 1 calc R U . . .
C6 C 0.54610(8) 0.51525(17) 0.19092(6) 0.0123(3) Uani 1 1 d . . . . .
H6A H 0.5333 0.4562 0.2277 0.015 Uiso 1 1 calc R U . . .
H6B H 0.5363 0.6307 0.1979 0.015 Uiso 1 1 calc R U . . .
C8 C 0.60047(9) 0.51604(17) 0.06686(6) 0.0137(3) Uani 1 1 d . . . . .
H8A H 0.6133 0.5750 0.0296 0.016 Uiso 1 1 calc R U . . .
C9 C 0.61444(9) 0.33604(18) 0.05753(6) 0.0154(3) Uani 1 1 d . . . . .
H9A H 0.5813 0.2966 0.0246 0.018 Uiso 1 1 calc R U . . .
H9B H 0.6700 0.3168 0.0471 0.018 Uiso 1 1 calc R U . . .
C10 C 0.51467(9) 0.54595(19) 0.08309(6) 0.0156(3) Uani 1 1 d . . . . .
H10A H 0.4803 0.5093 0.0505 0.019 Uiso 1 1 calc R U . . .
H10B H 0.5058 0.6622 0.0890 0.019 Uiso 1 1 calc R U . . .
C11 C 0.69582(8) 0.66934(16) 0.25352(6) 0.0104(2) Uani 1 1 d . . . . .
C12 C 0.77708(8) 0.76914(16) 0.33833(6) 0.0106(2) Uani 1 1 d . . . . .
C13 C 0.85588(9) 0.80530(17) 0.34672(6) 0.0137(3) Uani 1 1 d . . . . .
H13A H 0.8939 0.7654 0.3198 0.016 Uiso 1 1 calc R U . . .
C14 C 0.87940(9) 0.89946(17) 0.39434(7) 0.0160(3) Uani 1 1 d . . . . .
H14A H 0.9333 0.9232 0.4004 0.019 Uiso 1 1 calc R U . . .
C15 C 0.82321(10) 0.95804(17) 0.43279(6) 0.0146(3) Uani 1 1 d . . . . .
C16 C 0.74427(9) 0.92559(17) 0.42454(6) 0.0151(3) Uani 1 1 d . . . . .
H16A H 0.7063 0.9687 0.4508 0.018 Uiso 1 1 calc R U . . .
C17 C 0.72139(9) 0.82936(17) 0.37747(6) 0.0127(3) Uani 1 1 d . . . . .
H17A H 0.6676 0.8045 0.3720 0.015 Uiso 1 1 calc R U . . .
H1N1 H 0.7201(11) 0.465(2) 0.2302(8) 0.018(5) Uiso 1 1 d . . . . .
H1N2 H 0.7867(11) 0.576(2) 0.2892(8) 0.018(5) 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'
Br Br -0.2901 2.4595 '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 N1 C1 131.63(12) . .
C11 N1 H1N1 113.7(13) . .
C1 N1 H1N1 114.0(13) . .
C11 N2 C12 128.74(12) . .
C11 N2 H1N2 115.3(12) . .
C12 N2 H1N2 115.9(12) . .
N1 C1 C7 111.83(11) . .
N1 C1 C6 112.49(11) . .
C7 C1 C6 110.53(11) . .
N1 C1 C2 104.95(11) . .
C7 C1 C2 108.60(11) . .
C6 C1 C2 108.16(11) . .
C3 C2 C1 110.68(11) . .
C3 C2 H2A 109.5 . .
C1 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 108.1 . .
C2 C3 C9 109.36(12) . .
C2 C3 C4 109.13(12) . .
C9 C3 C4 109.71(12) . .
C2 C3 H3A 109.5 . .
C9 C3 H3A 109.5 . .
C4 C3 H3A 109.5 . .
C5 C4 C3 109.26(12) . .
C5 C4 H4A 109.8 . .
C3 C4 H4A 109.8 . .
C5 C4 H4B 109.8 . .
C3 C4 H4B 109.8 . .
H4A C4 H4B 108.3 . .
C4 C5 C10 109.36(12) . .
C4 C5 C6 109.98(12) . .
C10 C5 C6 109.67(12) . .
C4 C5 H5A 109.3 . .
C10 C5 H5A 109.3 . .
C6 C5 H5A 109.3 . .
C1 C7 C8 109.35(11) . .
C1 C7 H7A 109.8 . .
C8 C7 H7A 109.8 . .
C1 C7 H7B 109.8 . .
C8 C7 H7B 109.8 . .
H7A C7 H7B 108.3 . .
C5 C6 C1 109.16(11) . .
C5 C6 H6A 109.8 . .
C1 C6 H6A 109.8 . .
C5 C6 H6B 109.8 . .
C1 C6 H6B 109.8 . .
H6A C6 H6B 108.3 . .
C10 C8 C9 109.94(12) . .
C10 C8 C7 109.10(11) . .
C9 C8 C7 109.76(12) . .
C10 C8 H8A 109.3 . .
C9 C8 H8A 109.3 . .
C7 C8 H8A 109.3 . .
C3 C9 C8 109.03(11) . .
C3 C9 H9A 109.9 . .
C8 C9 H9A 109.9 . .
C3 C9 H9B 109.9 . .
C8 C9 H9B 109.9 . .
H9A C9 H9B 108.3 . .
C8 C10 C5 109.68(12) . .
C8 C10 H10A 109.7 . .
C5 C10 H10A 109.7 . .
C8 C10 H10B 109.7 . .
C5 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
N1 C11 N2 112.34(12) . .
N1 C11 S1 124.93(11) . .
N2 C11 S1 122.68(10) . .
C17 C12 C13 119.67(13) . .
C17 C12 N2 122.11(13) . .
C13 C12 N2 118.05(12) . .
C14 C13 C12 120.45(14) . .
C14 C13 H13A 119.8 . .
C12 C13 H13A 119.8 . .
C15 C14 C13 119.02(14) . .
C15 C14 H14A 120.5 . .
C13 C14 H14A 120.5 . .
C14 C15 C16 121.34(13) . .
C14 C15 Br1 119.39(12) . .
C16 C15 Br1 119.26(11) . .
C15 C16 C17 119.27(14) . .
C15 C16 H16A 120.4 . .
C17 C16 H16A 120.4 . .
C16 C17 C12 120.22(14) . .
C16 C17 H17A 119.9 . .
C12 C17 H17A 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C15 1.8993(14) .
S1 C11 1.6925(14) .
N1 C11 1.3406(18) .
N1 C1 1.4736(17) .
N1 H1N1 0.824(19) .
N2 C11 1.3675(17) .
N2 C12 1.4139(17) .
N2 H1N2 0.875(18) .
C1 C7 1.5364(19) .
C1 C6 1.5375(19) .
C1 C2 1.5396(19) .
C2 C3 1.530(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C9 1.532(2) .
C3 C4 1.534(2) .
C3 H3A 1.0000 .
C4 C5 1.530(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C10 1.533(2) .
C5 C6 1.5349(19) .
C5 H5A 1.0000 .
C7 C8 1.540(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C8 C10 1.530(2) .
C8 C9 1.535(2) .
C8 H8A 1.0000 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C12 C17 1.3920(19) .
C12 C13 1.391(2) .
C13 C14 1.391(2) .
C13 H13A 0.9500 .
C14 C15 1.383(2) .
C14 H14A 0.9500 .
C15 C16 1.387(2) .
C16 C17 1.3886(19) .
C16 H16A 0.9500 .
C17 H17A 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
C11 N1 C1 C7 68.20(19) . . . .
C11 N1 C1 C6 -56.9(2) . . . .
C11 N1 C1 C2 -174.25(14) . . . .
N1 C1 C2 C3 -179.33(11) . . . .
C7 C1 C2 C3 -59.60(15) . . . .
C6 C1 C2 C3 60.39(14) . . . .
C1 C2 C3 C9 59.96(15) . . . .
C1 C2 C3 C4 -60.06(15) . . . .
C2 C3 C4 C5 59.11(15) . . . .
C9 C3 C4 C5 -60.70(15) . . . .
C3 C4 C5 C10 60.20(15) . . . .
C3 C4 C5 C6 -60.29(15) . . . .
N1 C1 C7 C8 174.77(11) . . . .
C6 C1 C7 C8 -59.08(14) . . . .
C2 C1 C7 C8 59.43(14) . . . .
C4 C5 C6 C1 61.15(15) . . . .
C10 C5 C6 C1 -59.15(15) . . . .
N1 C1 C6 C5 -175.55(12) . . . .
C7 C1 C6 C5 58.67(15) . . . .
C2 C1 C6 C5 -60.11(14) . . . .
C1 C7 C8 C10 59.66(15) . . . .
C1 C7 C8 C9 -60.86(15) . . . .
C2 C3 C9 C8 -59.68(15) . . . .
C4 C3 C9 C8 59.99(15) . . . .
C10 C8 C9 C3 -59.43(15) . . . .
C7 C8 C9 C3 60.58(15) . . . .
C9 C8 C10 C5 59.55(15) . . . .
C7 C8 C10 C5 -60.87(15) . . . .
C4 C5 C10 C8 -59.76(15) . . . .
C6 C5 C10 C8 60.91(15) . . . .
C1 N1 C11 N2 -174.83(13) . . . .
C1 N1 C11 S1 2.7(2) . . . .
C12 N2 C11 N1 -167.94(13) . . . .
C12 N2 C11 S1 14.4(2) . . . .
C11 N2 C12 C17 45.3(2) . . . .
C11 N2 C12 C13 -139.45(15) . . . .
C17 C12 C13 C14 0.8(2) . . . .
N2 C12 C13 C14 -174.54(13) . . . .
C12 C13 C14 C15 -0.7(2) . . . .
C13 C14 C15 C16 -0.4(2) . . . .
C13 C14 C15 Br1 178.66(11) . . . .
C14 C15 C16 C17 1.5(2) . . . .
Br1 C15 C16 C17 -177.61(10) . . . .
C15 C16 C17 C12 -1.4(2) . . . .
C13 C12 C17 C16 0.3(2) . . . .
N2 C12 C17 C16 175.41(13) . . . .
