#------------------------------------------------------------------------------
#$Date: 2023-04-20 11:18:55 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107095.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_8107095
loop_
_publ_author_name
'Zhang, Jingfang'
'Liu, Yulong'
'Borjihan, Gereltu'
'He, Wei'
_publ_section_title
;
 Crystal structure of
 2-(bromomethyl)-4-(4-chlorophenyl)-1-tosylpyrrolidine, C18H19BrClNO2S2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1057
_journal_page_last               1058
_journal_paper_doi               10.1515/ncrs-2016-0049
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C18 H19 Br Cl N O2 S'
_chemical_formula_weight         428.76
_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_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.558(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.324(6)
_cell_length_b                   5.8597(16)
_cell_length_c                   14.966(4)
_cell_measurement_reflns_used    1315
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.55
_cell_measurement_theta_min      2.88
_cell_volume                     1861.2(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8828
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         0.96
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  0.7202
_exptl_absorpt_correction_T_min  0.4729
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.060
_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     218
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0454
_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)+(0.0409P)²+1.4768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1991
_reflns_number_total             3294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0049_suppl.cif
_cod_data_source_block           xb9154
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8107095
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.29445(3) 0.60745(12) 0.44266(4) 0.0902(3) Uani 1 1 d . . .
Cl1 Cl 0.55481(7) 0.1519(3) 0.93250(10) 0.0947(5) Uani 1 1 d . . .
S1 S 0.16851(6) 0.6687(2) 0.63876(10) 0.0631(4) Uani 1 1 d . . .
N1 N 0.23440(16) 0.5427(7) 0.6284(2) 0.0511(10) Uani 1 1 d . . .
O1 O 0.18312(17) 0.8940(5) 0.6708(3) 0.0904(13) Uani 1 1 d . . .
O2 O 0.13075(16) 0.6354(7) 0.5553(2) 0.0915(13) Uani 1 1 d . . .
C1 C 0.0315(3) 0.2131(12) 0.9264(4) 0.094(2) Uani 1 1 d . . .
H1A H 0.0465 0.2733 0.9842 0.140 Uiso 1 1 calc R . .
H1B H 0.0380 0.0510 0.9260 0.140 Uiso 1 1 calc R . .
H1C H -0.0126 0.2454 0.9142 0.140 Uiso 1 1 calc R . .
C2 C 0.0672(2) 0.3227(9) 0.8550(3) 0.0568(13) Uani 1 1 d . . .
C3 C 0.1022(2) 0.5152(11) 0.8729(3) 0.0733(16) Uani 1 1 d . . .
H3 H 0.1048 0.5764 0.9304 0.088 Uiso 1 1 calc R . .
C4 C 0.1337(2) 0.6219(9) 0.8084(4) 0.0661(14) Uani 1 1 d . . .
H4 H 0.1570 0.7535 0.8223 0.079 Uiso 1 1 calc R . .
C5 C 0.13026(19) 0.5312(7) 0.7232(3) 0.0455(11) Uani 1 1 d . . .
C6 C 0.0962(2) 0.3362(8) 0.7041(3) 0.0519(12) Uani 1 1 d . . .
H6 H 0.0940 0.2730 0.6469 0.062 Uiso 1 1 calc R . .
C7 C 0.0650(2) 0.2336(8) 0.7700(3) 0.0566(13) Uani 1 1 d . . .
H7 H 0.0419 0.1012 0.7566 0.068 Uiso 1 1 calc R . .
C8 C 0.2836(2) 0.5450(8) 0.7046(3) 0.0573(13) Uani 1 1 d . . .
H8A H 0.2666 0.5954 0.7591 0.069 Uiso 1 1 calc R . .
H8B H 0.3181 0.6449 0.6925 0.069 Uiso 1 1 calc R . .
C9 C 0.3054(2) 0.2989(7) 0.7128(3) 0.0499(11) Uani 1 1 d . . .
H9 H 0.2740 0.2137 0.7431 0.060 Uiso 1 1 calc R . .
C10 C 0.2997(2) 0.2250(8) 0.6152(3) 0.0542(12) Uani 1 1 d . . .
H10A H 0.3354 0.2783 0.5856 0.065 Uiso 1 1 calc R . .
H10B H 0.2974 0.0601 0.6104 0.065 Uiso 1 1 calc R . .
C11 C 0.2393(2) 0.3334(8) 0.5739(3) 0.0554(12) Uani 1 1 d . . .
H11 H 0.2044 0.2325 0.5856 0.066 Uiso 1 1 calc R . .
C12 C 0.2351(3) 0.3768(9) 0.4738(3) 0.0737(16) Uani 1 1 d . . .
H12A H 0.1927 0.4257 0.4532 0.088 Uiso 1 1 calc R . .
H12B H 0.2433 0.2357 0.4432 0.088 Uiso 1 1 calc R . .
C13 C 0.3686(2) 0.2659(8) 0.7663(3) 0.0513(12) Uani 1 1 d . . .
C14 C 0.4063(2) 0.0825(8) 0.7529(4) 0.0666(14) Uani 1 1 d . . .
H14 H 0.3934 -0.0204 0.7075 0.080 Uiso 1 1 calc R . .
C15 C 0.4627(2) 0.0444(9) 0.8044(4) 0.0679(15) Uani 1 1 d . . .
H15 H 0.4869 -0.0832 0.7943 0.082 Uiso 1 1 calc R . .
C16 C 0.4821(2) 0.1958(10) 0.8698(3) 0.0665(14) Uani 1 1 d . . .
C17 C 0.4470(3) 0.3828(11) 0.8847(4) 0.099(2) Uani 1 1 d . . .
H17 H 0.4608 0.4870 0.9292 0.118 Uiso 1 1 calc R . .
C18 C 0.3907(3) 0.4164(10) 0.8331(4) 0.0837(19) Uani 1 1 d . . .
H18 H 0.3667 0.5444 0.8437 0.100 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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'
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
O1 S1 O2 120.3(2) . .
O1 S1 N1 107.0(2) . .
O2 S1 N1 106.0(2) . .
O1 S1 C5 106.4(2) . .
O2 S1 C5 107.6(2) . .
N1 S1 C5 109.15(19) . .
C8 N1 C11 110.5(3) . .
C8 N1 S1 119.0(3) . .
C11 N1 S1 122.8(3) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 117.8(4) . .
C3 C2 C1 121.0(5) . .
C7 C2 C1 121.2(5) . .
C2 C3 C4 122.1(5) . .
C2 C3 H3 118.9 . .
C4 C3 H3 118.9 . .
C3 C4 C5 119.2(5) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C6 C5 C4 119.6(4) . .
C6 C5 S1 120.4(4) . .
C4 C5 S1 120.0(4) . .
C5 C6 C7 119.9(4) . .
C5 C6 H6 120.1 . .
C7 C6 H6 120.1 . .
C2 C7 C6 121.4(5) . .
C2 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
N1 C8 C9 104.1(4) . .
N1 C8 H8A 110.9 . .
C9 C8 H8A 110.9 . .
N1 C8 H8B 110.9 . .
C9 C8 H8B 110.9 . .
H8A C8 H8B 108.9 . .
C13 C9 C8 114.5(4) . .
C13 C9 C10 117.2(4) . .
C8 C9 C10 101.4(4) . .
C13 C9 H9 107.7 . .
C8 C9 H9 107.7 . .
C10 C9 H9 107.7 . .
C11 C10 C9 105.1(4) . .
C11 C10 H10A 110.7 . .
C9 C10 H10A 110.7 . .
C11 C10 H10B 110.7 . .
C9 C10 H10B 110.7 . .
H10A C10 H10B 108.8 . .
N1 C11 C10 103.0(4) . .
N1 C11 C12 113.9(4) . .
C10 C11 C12 116.2(4) . .
N1 C11 H11 107.8 . .
C10 C11 H11 107.8 . .
C12 C11 H11 107.8 . .
C11 C12 Br1 112.2(3) . .
C11 C12 H12A 109.2 . .
Br1 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
Br1 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C14 C13 C18 116.4(5) . .
C14 C13 C9 121.9(4) . .
C18 C13 C9 121.6(4) . .
C13 C14 C15 122.5(5) . .
C13 C14 H14 118.8 . .
C15 C14 H14 118.8 . .
C16 C15 C14 119.1(5) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
C15 C16 C17 120.8(5) . .
C15 C16 Cl1 118.9(4) . .
C17 C16 Cl1 120.3(5) . .
C16 C17 C18 119.2(5) . .
C16 C17 H17 120.4 . .
C18 C17 H17 120.4 . .
C17 C18 C13 122.1(5) . .
C17 C18 H18 118.9 . .
C13 C18 H18 118.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C12 1.939(5) .
Cl1 C16 1.751(5) .
S1 O1 1.429(4) .
S1 O2 1.432(4) .
S1 N1 1.608(4) .
S1 C5 1.764(4) .
N1 C8 1.473(5) .
N1 C11 1.483(6) .
C1 C2 1.515(7) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.364(7) .
C2 C7 1.371(6) .
C3 C4 1.377(7) .
C3 H3 0.9300 .
C4 C5 1.377(6) .
C4 H4 0.9300 .
C5 C6 1.370(6) .
C6 C7 1.380(6) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.517(6) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C13 1.512(6) .
C9 C10 1.518(6) .
C9 H9 0.9800 .
C10 C11 1.513(6) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.513(6) .
C11 H11 0.9800 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.367(6) .
C13 C18 1.382(6) .
C14 C15 1.382(7) .
C14 H14 0.9300 .
C15 C16 1.356(7) .
C15 H15 0.9300 .
C16 C17 1.358(7) .
C17 C18 1.378(7) .
C17 H17 0.9300 .
C18 H18 0.9300 .
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
O1 S1 N1 C8 51.0(4) . . . .
O2 S1 N1 C8 -179.4(3) . . . .
C5 S1 N1 C8 -63.8(4) . . . .
O1 S1 N1 C11 -162.4(3) . . . .
O2 S1 N1 C11 -32.8(4) . . . .
C5 S1 N1 C11 82.8(4) . . . .
C7 C2 C3 C4 1.1(8) . . . .
C1 C2 C3 C4 -178.1(5) . . . .
C2 C3 C4 C5 -0.4(8) . . . .
C3 C4 C5 C6 -0.5(7) . . . .
C3 C4 C5 S1 178.4(4) . . . .
O1 S1 C5 C6 163.2(4) . . . .
O2 S1 C5 C6 32.9(4) . . . .
N1 S1 C5 C6 -81.7(4) . . . .
O1 S1 C5 C4 -15.8(4) . . . .
O2 S1 C5 C4 -146.0(4) . . . .
N1 S1 C5 C4 99.4(4) . . . .
C4 C5 C6 C7 0.7(7) . . . .
S1 C5 C6 C7 -178.2(3) . . . .
C3 C2 C7 C6 -0.9(7) . . . .
C1 C2 C7 C6 178.3(5) . . . .
C5 C6 C7 C2 0.0(7) . . . .
C11 N1 C8 C9 -17.8(5) . . . .
S1 N1 C8 C9 132.6(3) . . . .
N1 C8 C9 C13 162.0(4) . . . .
N1 C8 C9 C10 34.8(4) . . . .
C13 C9 C10 C11 -165.4(4) . . . .
C8 C9 C10 C11 -40.0(4) . . . .
C8 N1 C11 C10 -7.0(5) . . . .
S1 N1 C11 C10 -156.1(3) . . . .
C8 N1 C11 C12 -133.7(4) . . . .
S1 N1 C11 C12 77.2(5) . . . .
C9 C10 C11 N1 29.2(4) . . . .
C9 C10 C11 C12 154.5(4) . . . .
N1 C11 C12 Br1 52.6(5) . . . .
C10 C11 C12 Br1 -66.9(5) . . . .
C8 C9 C13 C14 -154.2(5) . . . .
C10 C9 C13 C14 -35.6(6) . . . .
C8 C9 C13 C18 27.7(6) . . . .
C10 C9 C13 C18 146.3(5) . . . .
C18 C13 C14 C15 1.5(8) . . . .
C9 C13 C14 C15 -176.6(4) . . . .
C13 C14 C15 C16 -1.0(8) . . . .
C14 C15 C16 C17 -0.2(8) . . . .
C14 C15 C16 Cl1 -177.9(4) . . . .
C15 C16 C17 C18 0.8(10) . . . .
Cl1 C16 C17 C18 178.5(5) . . . .
C16 C17 C18 C13 -0.2(10) . . . .
C14 C13 C18 C17 -0.9(9) . . . .
C9 C13 C18 C17 177.2(6) . . . .
