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#$Date: 2022-10-21 10:02:44 +0300 (Fri, 21 Oct 2022) $
#$Revision: 278685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105918.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_8105918
loop_
_publ_author_name
'Al-Ghulikah, Hanan A.'
'Ghabbour, Hazem A.'
'Tiekink, Edward R.T.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of 4-bromobenzyl
 (Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C22H29BrN2OS
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1001
_journal_page_last               1003
_journal_paper_doi               10.1515/ncrs-2019-0216
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C22 H29 Br N2 O S'
_chemical_formula_sum            'C22 H29 Br N2 O S'
_chemical_formula_weight         449.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                73.607(2)
_cell_angle_beta                 84.7020(10)
_cell_angle_gamma                88.7210(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1722(3)
_cell_length_b                   10.2350(4)
_cell_length_c                   14.8756(6)
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.26
_cell_measurement_theta_min      2.83
_cell_volume                     1043.11(7)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29518
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.805
_diffrn_reflns_theta_min         2.074
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_max  0.8000
_exptl_absorpt_correction_T_min  0.4592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         8337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0319P)²+0.2184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5322
_reflns_number_total             8337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0216_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8105918
_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.
;
_shelx_estimated_absorpt_t_min   0.461
_shelx_estimated_absorpt_t_max   0.803
loop_
_space_group_symop_operation_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_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 1.20216(3) 0.36045(2) 0.54756(2) 0.02552(6) Uani 1 1 d . . . . .
S1 S 0.55468(6) 0.14208(4) 0.28378(3) 0.01351(9) Uani 1 1 d . . . . .
O1 O 1.14454(17) 0.01989(12) 0.07956(9) 0.0182(3) Uani 1 1 d . . . . .
N1 N 0.87498(18) 0.15584(14) 0.17322(9) 0.0113(3) Uani 1 1 d . . . . .
N2 N 0.73859(18) 0.36611(14) 0.16104(9) 0.0118(3) Uani 1 1 d . . . . .
C1 C 0.7319(2) 0.23870(16) 0.19672(11) 0.0108(3) Uani 1 1 d . . . . .
C2 C 0.7038(2) 0.03562(17) 0.36897(12) 0.0163(3) Uani 1 1 d . . . . .
H2A H 0.6252 -0.0259 0.4189 0.020 Uiso 1 1 calc R U . . .
H2B H 0.7840 -0.0192 0.3380 0.020 Uiso 1 1 calc R U . . .
C3 C 0.8239(2) 0.11681(16) 0.41139(11) 0.0140(3) Uani 1 1 d . . . . .
C4 C 1.0159(2) 0.12684(18) 0.38708(12) 0.0161(3) Uani 1 1 d . . . . .
H4 H 1.0697 0.0843 0.3435 0.019 Uiso 1 1 calc R U . . .
C5 C 1.1287(2) 0.19982(18) 0.42722(12) 0.0166(3) Uani 1 1 d . . . . .
H5 H 1.2571 0.2063 0.4107 0.020 Uiso 1 1 calc R U . . .
C6 C 1.0475(2) 0.26246(17) 0.49185(12) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.8560(3) 0.25542(18) 0.51715(12) 0.0196(4) Uani 1 1 d . . . . .
H7 H 0.8027 0.2982 0.5607 0.023 Uiso 1 1 calc R U . . .
C8 C 0.7465(2) 0.18307(18) 0.47583(12) 0.0181(4) Uani 1 1 d . . . . .
H8 H 0.6177 0.1786 0.4915 0.022 Uiso 1 1 calc R U . . .
C9 C 1.0376(2) 0.22895(17) 0.11485(12) 0.0146(3) Uani 1 1 d . . . . .
H9A H 1.0759 0.3009 0.1400 0.018 Uiso 1 1 calc R U . . .
H9B H 1.0053 0.2698 0.0511 0.018 Uiso 1 1 calc R U . . .
C10 C 1.1958(2) 0.12835(18) 0.11499(13) 0.0163(3) Uani 1 1 d . . . . .
H10A H 1.3042 0.1755 0.0767 0.020 Uiso 1 1 calc R U . . .
H10B H 1.2305 0.0911 0.1787 0.020 Uiso 1 1 calc R U . . .
C11 C 0.9860(2) -0.05104(17) 0.13587(13) 0.0175(4) Uani 1 1 d . . . . .
H11A H 1.0193 -0.0918 0.1995 0.021 Uiso 1 1 calc R U . . .
H11B H 0.9510 -0.1238 0.1108 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8209(2) 0.04254(17) 0.13826(12) 0.0142(3) Uani 1 1 d . . . . .
H12A H 0.7803 0.0779 0.0756 0.017 Uiso 1 1 calc R U . . .
H12B H 0.7175 -0.0077 0.1791 0.017 Uiso 1 1 calc R U . . .
C13 C 0.6064(2) 0.46803(16) 0.18183(11) 0.0111(3) Uani 1 1 d . . . . .
C14 C 0.5903(2) 0.47399(17) 0.28468(11) 0.0137(3) Uani 1 1 d . . . . .
H14A H 0.5425 0.3879 0.3261 0.016 Uiso 1 1 calc R U . . .
H14B H 0.7129 0.4895 0.3023 0.016 Uiso 1 1 calc R U . . .
C15 C 0.4107(2) 0.44547(17) 0.15427(12) 0.0139(3) Uani 1 1 d . . . . .
H15A H 0.4202 0.4413 0.0897 0.017 Uiso 1 1 calc R U . . .
H15B H 0.3600 0.3594 0.1943 0.017 Uiso 1 1 calc R U . . .
C16 C 0.6827(2) 0.60650(16) 0.11913(12) 0.0140(3) Uani 1 1 d . . . . .
H16A H 0.8054 0.6223 0.1367 0.017 Uiso 1 1 calc R U . . .
H16B H 0.6966 0.6048 0.0540 0.017 Uiso 1 1 calc R U . . .
C17 C 0.4575(2) 0.58975(17) 0.29518(12) 0.0166(4) Uani 1 1 d . . . . .
H17 H 0.4466 0.5923 0.3608 0.020 Uiso 1 1 calc R U . . .
C18 C 0.2631(2) 0.56547(18) 0.26744(13) 0.0192(4) Uani 1 1 d . . . . .
H18A H 0.1790 0.6379 0.2751 0.023 Uiso 1 1 calc R U . . .
H18B H 0.2121 0.4798 0.3080 0.023 Uiso 1 1 calc R U . . .
C19 C 0.2790(2) 0.56173(18) 0.16454(13) 0.0177(4) Uani 1 1 d . . . . .
H19 H 0.1549 0.5461 0.1468 0.021 Uiso 1 1 calc R U . . .
C20 C 0.3584(3) 0.69740(18) 0.10043(13) 0.0196(4) Uani 1 1 d . . . . .
H20A H 0.2746 0.7710 0.1059 0.024 Uiso 1 1 calc R U . . .
H20B H 0.3693 0.6949 0.0355 0.024 Uiso 1 1 calc R U . . .
C21 C 0.5518(2) 0.72245(17) 0.12900(12) 0.0164(4) Uani 1 1 d . . . . .
H21 H 0.6027 0.8092 0.0881 0.020 Uiso 1 1 calc R U . . .
C22 C 0.5343(3) 0.72672(17) 0.23178(12) 0.0178(4) Uani 1 1 d . . . . .
H22A H 0.6560 0.7442 0.2497 0.021 Uiso 1 1 calc R U . . .
H22B H 0.4506 0.7995 0.2390 0.021 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 0.0033 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'
Br Br -0.2901 2.4595 '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
C1 S1 C2 100.28(7) . .
C10 O1 C11 109.80(13) . .
C1 N1 C9 115.19(13) . .
C1 N1 C12 117.52(13) . .
C9 N1 C12 110.47(13) . .
C1 N2 C13 127.47(14) . .
N2 C1 N1 120.50(14) . .
N2 C1 S1 127.11(13) . .
N1 C1 S1 112.33(11) . .
C3 C2 S1 113.10(12) . .
C3 C2 H2A 109.0 . .
S1 C2 H2A 109.0 . .
C3 C2 H2B 109.0 . .
S1 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
C4 C3 C8 118.49(16) . .
C4 C3 C2 120.36(16) . .
C8 C3 C2 121.15(16) . .
C5 C4 C3 120.78(17) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C6 C5 C4 119.12(16) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
C7 C6 C5 121.59(17) . .
C7 C6 Br1 119.36(14) . .
C5 C6 Br1 119.05(13) . .
C6 C7 C8 118.26(17) . .
C6 C7 H7 120.9 . .
C8 C7 H7 120.9 . .
C7 C8 C3 121.74(16) . .
C7 C8 H8 119.1 . .
C3 C8 H8 119.1 . .
N1 C9 C10 108.47(13) . .
N1 C9 H9A 110.0 . .
C10 C9 H9A 110.0 . .
N1 C9 H9B 110.0 . .
C10 C9 H9B 110.0 . .
H9A C9 H9B 108.4 . .
O1 C10 C9 111.81(13) . .
O1 C10 H10A 109.3 . .
C9 C10 H10A 109.3 . .
O1 C10 H10B 109.3 . .
C9 C10 H10B 109.3 . .
H10A C10 H10B 107.9 . .
O1 C11 C12 111.76(14) . .
O1 C11 H11A 109.3 . .
C12 C11 H11A 109.3 . .
O1 C11 H11B 109.3 . .
C12 C11 H11B 109.3 . .
H11A C11 H11B 107.9 . .
N1 C12 C11 109.58(13) . .
N1 C12 H12A 109.8 . .
C11 C12 H12A 109.8 . .
N1 C12 H12B 109.8 . .
C11 C12 H12B 109.8 . .
H12A C12 H12B 108.2 . .
N2 C13 C15 110.43(13) . .
N2 C13 C16 105.34(13) . .
C15 C13 C16 108.81(13) . .
N2 C13 C14 115.05(13) . .
C15 C13 C14 109.22(13) . .
C16 C13 C14 107.74(13) . .
C17 C14 C13 109.61(13) . .
C17 C14 H14A 109.7 . .
C13 C14 H14A 109.7 . .
C17 C14 H14B 109.7 . .
C13 C14 H14B 109.7 . .
H14A C14 H14B 108.2 . .
C19 C15 C13 110.44(14) . .
C19 C15 H15A 109.6 . .
C13 C15 H15A 109.6 . .
C19 C15 H15B 109.6 . .
C13 C15 H15B 109.6 . .
H15A C15 H15B 108.1 . .
C21 C16 C13 111.17(13) . .
C21 C16 H16A 109.4 . .
C13 C16 H16A 109.4 . .
C21 C16 H16B 109.4 . .
C13 C16 H16B 109.4 . .
H16A C16 H16B 108.0 . .
C18 C17 C22 109.12(14) . .
C18 C17 C14 109.93(14) . .
C22 C17 C14 110.14(14) . .
C18 C17 H17 109.2 . .
C22 C17 H17 109.2 . .
C14 C17 H17 109.2 . .
C17 C18 C19 109.52(14) . .
C17 C18 H18A 109.8 . .
C19 C18 H18A 109.8 . .
C17 C18 H18B 109.8 . .
C19 C18 H18B 109.8 . .
H18A C18 H18B 108.2 . .
C20 C19 C15 109.47(14) . .
C20 C19 C18 109.72(15) . .
C15 C19 C18 108.90(14) . .
C20 C19 H19 109.6 . .
C15 C19 H19 109.6 . .
C18 C19 H19 109.6 . .
C19 C20 C21 109.49(14) . .
C19 C20 H20A 109.8 . .
C21 C20 H20A 109.8 . .
C19 C20 H20B 109.8 . .
C21 C20 H20B 109.8 . .
H20A C20 H20B 108.2 . .
C16 C21 C20 109.16(14) . .
C16 C21 C22 109.14(13) . .
C20 C21 C22 109.72(14) . .
C16 C21 H21 109.6 . .
C20 C21 H21 109.6 . .
C22 C21 H21 109.6 . .
C17 C22 C21 109.12(14) . .
C17 C22 H22A 109.9 . .
C21 C22 H22A 109.9 . .
C17 C22 H22B 109.9 . .
C21 C22 H22B 109.9 . .
H22A C22 H22B 108.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C6 1.9004(17) .
S1 C1 1.8167(16) .
S1 C2 1.8319(17) .
O1 C10 1.425(2) .
O1 C11 1.428(2) .
N1 C1 1.399(2) .
N1 C9 1.469(2) .
N1 C12 1.471(2) .
N2 C1 1.262(2) .
N2 C13 1.472(2) .
C2 C3 1.503(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.390(2) .
C3 C8 1.393(3) .
C4 C5 1.392(2) .
C4 H4 0.9300 .
C5 C6 1.379(3) .
C5 H5 0.9300 .
C6 C7 1.388(3) .
C7 C8 1.384(3) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C10 1.515(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.511(2) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C15 1.538(2) .
C13 C16 1.540(2) .
C13 C14 1.542(2) .
C14 C17 1.537(2) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C19 1.536(2) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C21 1.528(2) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.535(2) .
C17 C22 1.533(2) .
C17 H17 0.9800 .
C18 C19 1.536(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.533(3) .
C19 H19 0.9800 .
C20 C21 1.535(2) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.535(2) .
C21 H21 0.9800 .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
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
C13 N2 C1 N1 -176.37(14) . . . .
C13 N2 C1 S1 0.9(2) . . . .
C9 N1 C1 N2 6.9(2) . . . .
C12 N1 C1 N2 -125.98(16) . . . .
C9 N1 C1 S1 -170.70(11) . . . .
C12 N1 C1 S1 56.40(16) . . . .
C2 S1 C1 N2 -130.63(15) . . . .
C2 S1 C1 N1 46.80(13) . . . .
C1 S1 C2 C3 61.56(14) . . . .
S1 C2 C3 C4 -108.48(16) . . . .
S1 C2 C3 C8 71.76(18) . . . .
C8 C3 C4 C5 0.9(2) . . . .
C2 C3 C4 C5 -178.87(15) . . . .
C3 C4 C5 C6 0.0(2) . . . .
C4 C5 C6 C7 -0.6(3) . . . .
C4 C5 C6 Br1 179.35(12) . . . .
C5 C6 C7 C8 0.1(3) . . . .
Br1 C6 C7 C8 -179.79(13) . . . .
C6 C7 C8 C3 0.9(3) . . . .
C4 C3 C8 C7 -1.4(3) . . . .
C2 C3 C8 C7 178.41(15) . . . .
C1 N1 C9 C10 166.79(14) . . . .
C12 N1 C9 C10 -57.11(17) . . . .
C11 O1 C10 C9 -59.41(17) . . . .
N1 C9 C10 O1 58.98(18) . . . .
C10 O1 C11 C12 58.15(18) . . . .
C1 N1 C12 C11 -168.44(14) . . . .
C9 N1 C12 C11 56.60(17) . . . .
O1 C11 C12 N1 -57.01(18) . . . .
C1 N2 C13 C15 -63.1(2) . . . .
C1 N2 C13 C16 179.58(15) . . . .
C1 N2 C13 C14 61.1(2) . . . .
N2 C13 C14 C17 176.60(13) . . . .
C15 C13 C14 C17 -58.58(17) . . . .
C16 C13 C14 C17 59.46(17) . . . .
N2 C13 C15 C19 -173.08(13) . . . .
C16 C13 C15 C19 -57.92(17) . . . .
C14 C13 C15 C19 59.45(17) . . . .
N2 C13 C16 C21 176.56(13) . . . .
C15 C13 C16 C21 58.14(17) . . . .
C14 C13 C16 C21 -60.17(17) . . . .
C13 C14 C17 C18 59.49(17) . . . .
C13 C14 C17 C22 -60.79(18) . . . .
C22 C17 C18 C19 60.57(18) . . . .
C14 C17 C18 C19 -60.32(18) . . . .
C13 C15 C19 C20 59.82(18) . . . .
C13 C15 C19 C18 -60.14(17) . . . .
C17 C18 C19 C20 -59.75(18) . . . .
C17 C18 C19 C15 60.05(18) . . . .
C15 C19 C20 C21 -60.39(19) . . . .
C18 C19 C20 C21 59.06(18) . . . .
C13 C16 C21 C20 -59.46(18) . . . .
C13 C16 C21 C22 60.44(18) . . . .
C19 C20 C21 C16 59.98(18) . . . .
C19 C20 C21 C22 -59.57(18) . . . .
C18 C17 C22 C21 -60.83(18) . . . .
C14 C17 C22 C21 59.93(18) . . . .
C16 C21 C22 C17 -59.04(18) . . . .
C20 C21 C22 C17 60.52(18) . . . .
