#------------------------------------------------------------------------------
#$Date: 2022-03-25 09:38:15 +0200 (Fri, 25 Mar 2022) $
#$Revision: 273965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104851.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_8104851
loop_
_publ_author_name
'Bari, Ahmed'
'Hosten, Eric C.'
'Abdulrahman, AlObaid'
'Usman, Ghani'
_publ_section_title
;
 The crystal structure of N-(adamantan-1-yl)-piperidine-1-carbothioamide,
 C16H26N2S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              429
_journal_page_last               430
_journal_paper_doi               10.1515/ncrs-2020-0609
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C16 H26 N2 S'
_chemical_formula_sum            'C16 H26 N2 S'
_chemical_formula_weight         278.45
_chemical_melting_point          458.15
_chemical_name_common
;
N-(Adamantan-1-yl)-piperidine-1-carbothioamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 92.014(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4855(4)
_cell_length_b                   20.1110(12)
_cell_length_c                   11.2575(7)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      3.30
_cell_volume                     1467.41(16)
_computing_cell_refinement       'Bruker [1]'
_computing_data_collection       'Bruker [1]'
_computing_data_reduction        'Bruker [1]'
_computing_molecular_graphics    'Ortep [5]'
_computing_publication_material  'PLATON [6] and MERCURY [7]'
_computing_structure_refinement  'SHELXL [3] and ShelXle [4]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31238
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_min         2.025
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.632
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0324
_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)+(0.0443P)²+0.4616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3197
_reflns_number_total             3649
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0609_suppl.cif
_cod_data_source_block           ka184
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104851
_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   0.879
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
S1 S 0.14338(4) 0.62127(2) 0.49443(3) 0.03099(10) Uani 1 1 d . . . . .
N1 N 0.51615(15) 0.65768(5) 0.58063(9) 0.0258(2) Uani 1 1 d . . . . .
N2 N 0.42327(15) 0.54964(5) 0.61764(9) 0.0269(2) Uani 1 1 d . . . . .
C1 C 0.53564(15) 0.72243(5) 0.51914(9) 0.0186(2) Uani 1 1 d . . . . .
C2 C 0.36573(16) 0.77204(5) 0.54965(9) 0.0214(2) Uani 1 1 d . . . . .
H2A H 0.361900 0.777542 0.636934 0.026 Uiso 1 1 calc R U . . .
H2B H 0.229918 0.754948 0.520676 0.026 Uiso 1 1 calc R U . . .
C3 C 0.40885(16) 0.83942(5) 0.49113(10) 0.0227(2) Uani 1 1 d . . . . .
H3 H 0.296723 0.871442 0.510118 0.027 Uiso 1 1 calc R U . . .
C4 C 0.41424(17) 0.83028(6) 0.35653(10) 0.0252(2) Uani 1 1 d . . . . .
H4A H 0.439906 0.873645 0.318139 0.030 Uiso 1 1 calc R U . . .
H4B H 0.279379 0.813273 0.325836 0.030 Uiso 1 1 calc R U . . .
C5 C 0.58507(16) 0.78119(6) 0.32631(9) 0.0236(2) Uani 1 1 d . . . . .
H5 H 0.588147 0.775612 0.238121 0.028 Uiso 1 1 calc R U . . .
C6 C 0.79301(17) 0.80836(6) 0.37298(10) 0.0271(2) Uani 1 1 d . . . . .
H6A H 0.904487 0.776923 0.353787 0.033 Uiso 1 1 calc R U . . .
H6B H 0.821693 0.851436 0.334330 0.033 Uiso 1 1 calc R U . . .
C7 C 0.78747(16) 0.81778(5) 0.50745(10) 0.0230(2) Uani 1 1 d . . . . .
H7 H 0.923717 0.835082 0.538171 0.028 Uiso 1 1 calc R U . . .
C8 C 0.74292(16) 0.75089(5) 0.56604(10) 0.0220(2) Uani 1 1 d . . . . .
H8A H 0.739149 0.756802 0.653241 0.026 Uiso 1 1 calc R U . . .
H8B H 0.854957 0.719170 0.549298 0.026 Uiso 1 1 calc R U . . .
C9 C 0.54378(16) 0.71377(5) 0.38415(9) 0.0221(2) Uani 1 1 d . . . . .
H9A H 0.654715 0.682095 0.365122 0.027 Uiso 1 1 calc R U . . .
H9B H 0.411094 0.695517 0.352578 0.027 Uiso 1 1 calc R U . . .
C10 C 0.61694(17) 0.86709(5) 0.53740(11) 0.0254(2) Uani 1 1 d . . . . .
H10A H 0.643561 0.910629 0.499866 0.030 Uiso 1 1 calc R U . . .
H10B H 0.614575 0.873635 0.624503 0.030 Uiso 1 1 calc R U . . .
C11 C 0.37282(17) 0.60922(5) 0.56799(9) 0.0222(2) Uani 1 1 d . . . . .
C12 C 0.27274(19) 0.49579(6) 0.62979(11) 0.0308(3) Uani 1 1 d . . . . .
H12A H 0.322315 0.455324 0.589646 0.037 Uiso 1 1 calc R U . . .
H12B H 0.139363 0.508913 0.591210 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2426(2) 0.48108(7) 0.76015(12) 0.0354(3) Uani 1 1 d . . . . .
H13A H 0.147168 0.442992 0.767247 0.042 Uiso 1 1 calc R U . . .
H13B H 0.179208 0.520143 0.797987 0.042 Uiso 1 1 calc R U . . .
C14 C 0.4463(2) 0.46491(7) 0.82473(12) 0.0390(3) Uani 1 1 d . . . . .
H14A H 0.498674 0.421797 0.795882 0.047 Uiso 1 1 calc R U . . .
H14B H 0.424012 0.460654 0.910940 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6063(2) 0.51906(6) 0.80432(11) 0.0315(3) Uani 1 1 d . . . . .
H15A H 0.564713 0.560596 0.844144 0.038 Uiso 1 1 calc R U . . .
H15B H 0.741749 0.505107 0.839137 0.038 Uiso 1 1 calc R U . . .
C16 C 0.62444(17) 0.53150(6) 0.67231(10) 0.0264(2) Uani 1 1 d . . . . .
H16A H 0.724389 0.567835 0.659914 0.032 Uiso 1 1 calc R U . . .
H16B H 0.676761 0.490925 0.633714 0.032 Uiso 1 1 calc R U . . .
H1 H 0.619(2) 0.6474(8) 0.6210(14) 0.038(4) 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'
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 130.87(9) . .
C11 N1 H1 114.8(11) . .
C1 N1 H1 113.6(11) . .
C11 N2 C12 122.56(10) . .
C11 N2 C16 126.12(9) . .
C12 N2 C16 111.20(9) . .
N1 C1 C9 111.70(8) . .
N1 C1 C2 113.14(8) . .
C9 C1 C2 110.24(8) . .
N1 C1 C8 104.75(8) . .
C9 C1 C8 108.83(8) . .
C2 C1 C8 107.89(8) . .
C1 C2 C3 109.54(8) . .
C1 C2 H2A 109.8 . .
C3 C2 H2A 109.8 . .
C1 C2 H2B 109.8 . .
C3 C2 H2B 109.8 . .
H2A C2 H2B 108.2 . .
C4 C3 C10 109.26(9) . .
C4 C3 C2 109.26(9) . .
C10 C3 C2 110.21(9) . .
C4 C3 H3 109.4 . .
C10 C3 H3 109.4 . .
C2 C3 H3 109.4 . .
C3 C4 C5 109.87(8) . .
C3 C4 H4A 109.7 . .
C5 C4 H4A 109.7 . .
C3 C4 H4B 109.7 . .
C5 C4 H4B 109.7 . .
H4A C4 H4B 108.2 . .
C6 C5 C4 109.22(9) . .
C6 C5 C9 109.58(9) . .
C4 C5 C9 109.73(9) . .
C6 C5 H5 109.4 . .
C4 C5 H5 109.4 . .
C9 C5 H5 109.4 . .
C7 C6 C5 109.47(8) . .
C7 C6 H6A 109.8 . .
C5 C6 H6A 109.8 . .
C7 C6 H6B 109.8 . .
C5 C6 H6B 109.8 . .
H6A C6 H6B 108.2 . .
C6 C7 C8 109.24(9) . .
C6 C7 C10 109.93(9) . .
C8 C7 C10 109.00(9) . .
C6 C7 H7 109.6 . .
C8 C7 H7 109.6 . .
C10 C7 H7 109.6 . .
C7 C8 C1 110.81(8) . .
C7 C8 H8A 109.5 . .
C1 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C1 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
C5 C9 C1 109.48(8) . .
C5 C9 H9A 109.8 . .
C1 C9 H9A 109.8 . .
C5 C9 H9B 109.8 . .
C1 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
C7 C10 C3 108.90(8) . .
C7 C10 H10A 109.9 . .
C3 C10 H10A 109.9 . .
C7 C10 H10B 109.9 . .
C3 C10 H10B 109.9 . .
H10A C10 H10B 108.3 . .
N1 C11 N2 116.00(10) . .
N1 C11 S1 122.51(8) . .
N2 C11 S1 121.48(8) . .
N2 C12 C13 110.04(10) . .
N2 C12 H12A 109.7 . .
C13 C12 H12A 109.7 . .
N2 C12 H12B 109.7 . .
C13 C12 H12B 109.7 . .
H12A C12 H12B 108.2 . .
C12 C13 C14 111.42(11) . .
C12 C13 H13A 109.3 . .
C14 C13 H13A 109.3 . .
C12 C13 H13B 109.3 . .
C14 C13 H13B 109.3 . .
H13A C13 H13B 108.0 . .
C13 C14 C15 111.03(10) . .
C13 C14 H14A 109.4 . .
C15 C14 H14A 109.4 . .
C13 C14 H14B 109.4 . .
C15 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C16 C15 C14 109.99(10) . .
C16 C15 H15A 109.7 . .
C14 C15 H15A 109.7 . .
C16 C15 H15B 109.7 . .
C14 C15 H15B 109.7 . .
H15A C15 H15B 108.2 . .
N2 C16 C15 110.69(10) . .
N2 C16 H16A 109.5 . .
C15 C16 H16A 109.5 . .
N2 C16 H16B 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C11 1.6947(11) .
N1 C11 1.3508(14) .
N1 C1 1.4823(13) .
N1 H1 0.819(16) .
N2 C11 1.3574(14) .
N2 C12 1.4676(14) .
N2 C16 1.4689(14) .
C1 C9 1.5323(14) .
C1 C2 1.5344(14) .
C1 C8 1.5374(13) .
C2 C3 1.5368(15) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.5281(15) .
C3 C10 1.5339(15) .
C3 H3 1.0000 .
C4 C5 1.5312(15) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.5309(15) .
C5 C9 1.5317(15) .
C5 H5 1.0000 .
C6 C7 1.5272(16) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.5302(15) .
C7 C10 1.5318(15) .
C7 H7 1.0000 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C12 C13 1.5164(18) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.5205(19) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.5269(18) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.5156(16) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2B S1 0.99 2.76 3.4054(11) 123 . yes
C8 H8B S1 0.99 2.80 3.7866(11) 175 1_655 yes
C9 H9B S1 0.99 2.83 3.4601(11) 122 . yes
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 C9 -57.19(15) . . . .
C11 N1 C1 C2 67.91(15) . . . .
C11 N1 C1 C8 -174.83(11) . . . .
N1 C1 C2 C3 174.99(8) . . . .
C9 C1 C2 C3 -59.13(11) . . . .
C8 C1 C2 C3 59.59(11) . . . .
C1 C2 C3 C4 59.45(11) . . . .
C1 C2 C3 C10 -60.61(11) . . . .
C10 C3 C4 C5 60.47(11) . . . .
C2 C3 C4 C5 -60.18(11) . . . .
C3 C4 C5 C6 -59.96(11) . . . .
C3 C4 C5 C9 60.18(11) . . . .
C4 C5 C6 C7 59.46(12) . . . .
C9 C5 C6 C7 -60.77(11) . . . .
C5 C6 C7 C8 59.40(11) . . . .
C5 C6 C7 C10 -60.15(12) . . . .
C6 C7 C8 C1 -59.12(11) . . . .
C10 C7 C8 C1 61.01(11) . . . .
N1 C1 C8 C7 178.57(9) . . . .
C9 C1 C8 C7 58.99(11) . . . .
C2 C1 C8 C7 -60.63(11) . . . .
C6 C5 C9 C1 60.89(11) . . . .
C4 C5 C9 C1 -59.03(11) . . . .
N1 C1 C9 C5 -174.50(8) . . . .
C2 C1 C9 C5 58.81(10) . . . .
C8 C1 C9 C5 -59.34(10) . . . .
C6 C7 C10 C3 60.29(11) . . . .
C8 C7 C10 C3 -59.42(11) . . . .
C4 C3 C10 C7 -60.13(11) . . . .
C2 C3 C10 C7 59.94(11) . . . .
C1 N1 C11 N2 165.39(11) . . . .
C1 N1 C11 S1 -14.42(17) . . . .
C12 N2 C11 N1 169.21(10) . . . .
C16 N2 C11 N1 -6.57(17) . . . .
C12 N2 C11 S1 -10.97(16) . . . .
C16 N2 C11 S1 173.24(9) . . . .
C11 N2 C12 C13 -116.15(12) . . . .
C16 N2 C12 C13 60.20(13) . . . .
N2 C12 C13 C14 -55.73(14) . . . .
C12 C13 C14 C15 52.66(15) . . . .
C13 C14 C15 C16 -52.77(15) . . . .
C11 N2 C16 C15 114.66(12) . . . .
C12 N2 C16 C15 -61.53(12) . . . .
C14 C15 C16 N2 57.01(13) . . . .
