#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:12:46 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/06/7230620.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_7230620
loop_
_publ_author_name
'Voronin, Alexander P.'
'Volkova, Tatiana V.'
'Ilyukhin, Andrey B.'
'Trofimova, Tatiana P.'
'Perlovich, German L.'
_publ_section_title
;
 Structural and energetic aspects of adamantane and memantine derivatives
 of sulfonamide molecular crystals: experimental and theoretical
 characterisation
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              3476
_journal_paper_doi               10.1039/C8CE00426A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C18 H24 Br N O2 S'
_chemical_formula_sum            'C18 H24 Br N O2 S'
_chemical_formula_weight         398.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-12-08T21:18:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-12-09 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.420(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5014(3)
_cell_length_b                   15.4718(4)
_cell_length_c                   11.3326(3)
_cell_measurement_reflns_used    4153
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      35.75
_cell_measurement_theta_min      3.11
_cell_volume                     1766.17(9)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.206
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.839
_diffrn_reflns_theta_min         3.232
_diffrn_standards_number         16653
_exptl_absorpt_coefficient_mu    2.455
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SCALE3
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       ' prism'
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         7633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0
_reflns_number_gt                5678
_reflns_number_total             7633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00426a2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7230615--7230621.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7230620
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br Br 0.04606(2) 0.66763(2) 0.92323(2) 0.02965(5) Uani 1 1 d
S S -0.16457(3) 0.58420(2) 1.39032(3) 0.01354(6) Uani 1 1 d
O1 O -0.05438(10) 0.59986(7) 1.49795(10) 0.0191(2) Uani 1 1 d
O2 O -0.28337(10) 0.63412(7) 1.37433(9) 0.01736(19) Uani 1 1 d
N1 N -0.19732(11) 0.48340(7) 1.39357(11) 0.0148(2) Uani 1 1 d
H1A H -0.132(2) 0.4533(13) 1.4265(18) 0.025(5) Uiso 1 1 d
C1 C -0.10640(13) 0.60565(9) 1.26074(13) 0.0149(2) Uani 1 1 d
C2 C -0.00505(14) 0.55571(10) 1.23905(14) 0.0203(3) Uani 1 1 d
H2A H 0.031(2) 0.5094(14) 1.2892(19) 0.030(5) Uiso 1 1 d
C3 C 0.04050(15) 0.57378(11) 1.13783(15) 0.0226(3) Uani 1 1 d
H3A H 0.114(2) 0.5391(15) 1.123(2) 0.035(6) Uiso 1 1 d
C4 C -0.01517(15) 0.64211(10) 1.06136(14) 0.0199(3) Uani 1 1 d
C5 C -0.11558(16) 0.69255(11) 1.08250(15) 0.0233(3) Uani 1 1 d
H5A H -0.156(2) 0.7362(16) 1.025(2) 0.041(6) Uiso 1 1 d
C6 C -0.16161(16) 0.67352(10) 1.18295(15) 0.0209(3) Uani 1 1 d
H6A H -0.230(2) 0.7074(14) 1.2019(18) 0.028(5) Uiso 1 1 d
C7 C -0.31453(12) 0.43685(8) 1.31403(11) 0.0126(2) Uani 1 1 d
C8 C -0.34293(14) 0.46154(10) 1.17783(12) 0.0160(2) Uani 1 1 d
H8A H -0.3648(17) 0.5240(12) 1.1661(16) 0.014(4) Uiso 1 1 d
H8B H -0.2662(18) 0.4504(12) 1.1483(17) 0.019(4) Uiso 1 1 d
C9 C -0.46067(14) 0.40796(10) 1.10186(12) 0.0180(3) Uani 1 1 d
H9A H -0.4761(19) 0.4226(13) 1.0149(17) 0.024(5) Uiso 1 1 d
C10 C -0.58289(14) 0.42728(10) 1.14544(13) 0.0184(3) Uani 1 1 d
H10A H -0.6610(18) 0.3947(12) 1.0969(16) 0.018(4) Uiso 1 1 d
H10B H -0.6049(18) 0.4898(12) 1.1351(17) 0.018(4) Uiso 1 1 d
C11 C -0.55697(13) 0.40219(9) 1.28158(12) 0.0159(2) Uani 1 1 d
C12 C -0.43744(13) 0.45471(9) 1.35781(12) 0.0148(2) Uani 1 1 d
H12A H -0.4582(18) 0.5169(12) 1.3535(17) 0.018(4) Uiso 1 1 d
H12B H -0.4176(18) 0.4384(13) 1.4452(17) 0.022(5) Uiso 1 1 d
C13 C -0.28055(14) 0.34054(9) 1.32932(13) 0.0168(2) Uani 1 1 d
H13A H -0.267(2) 0.3261(12) 1.418(2) 0.027(5) Uiso 1 1 d
H13B H -0.2006(19) 0.3292(12) 1.3029(18) 0.019(5) Uiso 1 1 d
C14 C -0.39732(14) 0.28576(9) 1.25379(13) 0.0182(3) Uani 1 1 d
C15 C -0.52118(15) 0.30593(10) 1.29550(13) 0.0184(3) Uani 1 1 d
H15A H -0.5896(18) 0.2725(12) 1.2448(17) 0.021(5) Uiso 1 1 d
H15B H -0.501(2) 0.2898(13) 1.3825(19) 0.027(5) Uiso 1 1 d
C16 C -0.42718(16) 0.31181(10) 1.11796(13) 0.0205(3) Uani 1 1 d
H16A H -0.351(2) 0.3008(13) 1.0869(18) 0.026(5) Uiso 1 1 d
H16B H -0.499(2) 0.2745(13) 1.0672(17) 0.024(5) Uiso 1 1 d
C17 C -0.36329(19) 0.18990(11) 1.26960(19) 0.0306(4) Uani 1 1 d
H17A H -0.284(2) 0.1781(13) 1.2387(19) 0.025(5) Uiso 1 1 d
H17B H -0.437(2) 0.1549(15) 1.221(2) 0.043(7) Uiso 1 1 d
H17C H -0.343(2) 0.1707(14) 1.354(2) 0.037(6) Uiso 1 1 d
C18 C -0.67866(16) 0.42088(13) 1.32551(17) 0.0269(3) Uani 1 1 d
H18A H -0.763(2) 0.3901(14) 1.2707(18) 0.028(5) Uiso 1 1 d
H18B H -0.703(2) 0.4836(15) 1.320(2) 0.034(6) Uiso 1 1 d
H18C H -0.661(2) 0.4023(17) 1.407(2) 0.053(7) 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 0 '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 0.006 '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
O2 S O1 118.47(6)
O2 S N1 110.05(6)
O1 S N1 105.67(6)
O2 S C1 106.58(6)
O1 S C1 106.65(7)
N1 S C1 109.15(6)
C7 N1 S 127.13(9)
C7 N1 H1A 116.0(14)
S N1 H1A 114.0(15)
C6 C1 C2 120.71(14)
C6 C1 S 119.18(11)
C2 C1 S 120.11(11)
C3 C2 C1 119.50(14)
C3 C2 H2A 119.0(14)
C1 C2 H2A 121.5(14)
C4 C3 C2 119.10(14)
C4 C3 H3A 121.3(13)
C2 C3 H3A 119.6(13)
C5 C4 C3 121.87(14)
C5 C4 Br 118.55(12)
C3 C4 Br 119.57(12)
C4 C5 C6 118.72(14)
C4 C5 H5A 119.3(14)
C6 C5 H5A 121.8(14)
C1 C6 C5 120.10(14)
C1 C6 H6A 118.4(13)
C5 C6 H6A 121.5(12)
N1 C7 C13 106.01(10)
N1 C7 C12 110.14(11)
C13 C7 C12 109.24(11)
N1 C7 C8 112.36(11)
C13 C7 C8 109.20(11)
C12 C7 C8 109.78(11)
C9 C8 C7 109.05(11)
C9 C8 H8A 109.3(10)
C7 C8 H8A 110.4(10)
C9 C8 H8B 109.1(11)
C7 C8 H8B 111.0(11)
H8A C8 H8B 108.0(15)
C16 C9 C10 109.73(12)
C16 C9 C8 109.71(12)
C10 C9 C8 109.26(12)
C16 C9 H9A 108.2(12)
C10 C9 H9A 111.4(11)
C8 C9 H9A 108.5(12)
C9 C10 C11 110.35(11)
C9 C10 H10A 111.2(11)
C11 C10 H10A 108.3(11)
C9 C10 H10B 109.9(11)
C11 C10 H10B 109.5(11)
H10A C10 H10B 107.6(15)
C18 C11 C15 110.76(12)
C18 C11 C10 110.65(12)
C15 C11 C10 108.47(11)
C18 C11 C12 110.03(12)
C15 C11 C12 108.53(11)
C10 C11 C12 108.34(11)
C7 C12 C11 110.54(11)
C7 C12 H12A 110.8(11)
C11 C12 H12A 110.7(10)
C7 C12 H12B 108.7(11)
C11 C12 H12B 109.6(11)
H12A C12 H12B 106.4(16)
C7 C13 C14 110.49(11)
C7 C13 H13A 107.2(11)
C14 C13 H13A 107.6(12)
C7 C13 H13B 109.3(11)
C14 C13 H13B 110.3(11)
H13A C13 H13B 111.9(17)
C17 C14 C16 110.36(13)
C17 C14 C15 110.63(13)
C16 C14 C15 107.72(12)
C17 C14 C13 110.33(12)
C16 C14 C13 108.57(12)
C15 C14 C13 109.17(12)
C11 C15 C14 111.71(11)
C11 C15 H15A 110.4(12)
C14 C15 H15A 105.5(12)
C11 C15 H15B 109.1(12)
C14 C15 H15B 107.4(12)
H15A C15 H15B 112.6(17)
C9 C16 C14 110.50(12)
C9 C16 H16A 108.2(12)
C14 C16 H16A 111.2(12)
C9 C16 H16B 112.8(11)
C14 C16 H16B 109.6(12)
H16A C16 H16B 104.5(17)
C14 C17 H17A 109.0(11)
C14 C17 H17B 110.6(14)
H17A C17 H17B 107.8(19)
C14 C17 H17C 113.2(13)
H17A C17 H17C 108.2(18)
H17B C17 H17C 108(2)
C11 C18 H18A 111.6(12)
C11 C18 H18B 112.4(13)
H18A C18 H18B 104.4(16)
C11 C18 H18C 108.4(16)
H18A C18 H18C 110.2(19)
H18B C18 H18C 110(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C4 1.8944(15)
S O2 1.4346(10)
S O1 1.4448(10)
S N1 1.5996(12)
S C1 1.7740(14)
N1 C7 1.4897(17)
N1 H1A 0.82(2)
C1 C6 1.388(2)
C1 C2 1.392(2)
C2 C3 1.390(2)
C2 H2A 0.93(2)
C3 C4 1.387(2)
C3 H3A 0.99(2)
C4 C5 1.386(2)
C5 C6 1.388(2)
C5 H5A 0.95(2)
C6 H6A 0.96(2)
C7 C13 1.5306(19)
C7 C12 1.5331(19)
C7 C8 1.5353(18)
C8 C9 1.5347(19)
C8 H8A 0.993(18)
C8 H8B 0.972(19)
C9 C16 1.528(2)
C9 C10 1.529(2)
C9 H9A 0.979(19)
C10 C11 1.5388(19)
C10 H10A 0.987(18)
C10 H10B 0.994(19)
C11 C18 1.524(2)
C11 C15 1.533(2)
C11 C12 1.5392(19)
C12 H12A 0.984(18)
C12 H12B 0.985(19)
C13 C14 1.5366(19)
C13 H13A 1.00(2)
C13 H13B 0.98(2)
C14 C17 1.524(2)
C14 C16 1.535(2)
C14 C15 1.536(2)
C15 H15A 0.938(19)
C15 H15B 0.98(2)
C16 H16A 0.97(2)
C16 H16B 0.99(2)
C17 H17A 1.01(2)
C17 H17B 0.98(2)
C17 H17C 0.97(2)
C18 H18A 1.04(2)
C18 H18B 1.00(2)
C18 H18C 0.93(3)
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
N1 H1A O1 0.82(2) 2.07(2) 2.8845(15) 168(2) 3_568
C12 H12A O2 0.984(18) 2.544(18) 3.1917(17) 123.3(13) .
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
O2 S N1 C7 41.21(13)
O1 S N1 C7 170.22(11)
C1 S N1 C7 -75.43(13)
O2 S C1 C6 11.91(13)
O1 S C1 C6 -115.54(12)
N1 S C1 C6 130.74(12)
O2 S C1 C2 -169.17(11)
O1 S C1 C2 63.38(13)
N1 S C1 C2 -50.34(13)
C6 C1 C2 C3 -0.5(2)
S C1 C2 C3 -179.36(12)
C1 C2 C3 C4 0.8(2)
C2 C3 C4 C5 -0.4(2)
C2 C3 C4 Br 179.90(12)
C3 C4 C5 C6 -0.3(2)
Br C4 C5 C6 179.38(12)
C2 C1 C6 C5 -0.3(2)
S C1 C6 C5 178.64(12)
C4 C5 C6 C1 0.6(2)
S N1 C7 C13 165.07(10)
S N1 C7 C12 -76.87(14)
S N1 C7 C8 45.85(16)
N1 C7 C8 C9 177.46(11)
C13 C7 C8 C9 60.13(14)
C12 C7 C8 C9 -59.61(15)
C7 C8 C9 C16 -59.98(15)
C7 C8 C9 C10 60.35(15)
C16 C9 C10 C11 59.17(15)
C8 C9 C10 C11 -61.15(15)
C9 C10 C11 C18 -179.74(13)
C9 C10 C11 C15 -58.06(15)
C9 C10 C11 C12 59.57(15)
N1 C7 C12 C11 -176.28(11)
C13 C7 C12 C11 -60.23(14)
C8 C7 C12 C11 59.48(14)
C18 C11 C12 C7 -179.69(12)
C15 C11 C12 C7 58.97(14)
C10 C11 C12 C7 -58.61(15)
N1 C7 C13 C14 178.23(11)
C12 C7 C13 C14 59.57(14)
C8 C7 C13 C14 -60.50(15)
C7 C13 C14 C17 -179.81(14)
C7 C13 C14 C16 59.14(15)
C7 C13 C14 C15 -58.04(15)
C18 C11 C15 C14 -179.04(12)
C10 C11 C15 C14 59.34(14)
C12 C11 C15 C14 -58.16(14)
C17 C14 C15 C11 179.52(12)
C16 C14 C15 C11 -59.79(15)
C13 C14 C15 C11 57.92(15)
C10 C9 C16 C14 -60.18(15)
C8 C9 C16 C14 59.87(15)
C17 C14 C16 C9 -179.72(13)
C15 C14 C16 C9 59.42(15)
C13 C14 C16 C9 -58.68(15)
