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#$Date: 2024-07-05 18:32:37 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292970 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/85/7248557.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_7248557
loop_
_publ_author_name
'Yeo, Chien Ing'
'Kwong, Huey Chong'
'Tan, Sang Loon'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Variable non-covalent interactions in the crystals of a series of
 4-Y-benzyl pyrrolidine-1-carbodithioates: Y = Cl, Br, I, Me and NO2
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              2711
_journal_page_last               2722
_journal_paper_doi               10.1039/D4CE00158C
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C12 H14 N2 O2 S2'
_chemical_formula_sum            'C12 H14 N2 O2 S2'
_chemical_formula_weight         282.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-02-17 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9471(5)
_cell_length_b                   11.0713(3)
_cell_length_c                   8.2857(3)
_cell_measurement_reflns_used    5643
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4990
_cell_measurement_theta_min      5.0620
_cell_volume                     1279.42(7)
_computing_cell_refinement
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_collection
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8946
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.047
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_min         5.101
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.746
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.067
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0717P)²+0.2125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2169
_reflns_number_total             2255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00158c2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7248556--7248560.cif.'
_cod_database_code               7248557
_shelx_shelxl_version_number     2018/3
_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   0.787
_shelx_estimated_absorpt_t_max   0.847
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'
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 0.36599(7) 0.67729(8) 0.45589(12) 0.0176(3) Uani 1 1 d . . . . .
S2 S 0.38231(6) 0.40387(7) 0.49568(12) 0.0166(3) Uani 1 1 d . . . . .
O1 O -0.1114(2) 0.5436(3) 0.2327(4) 0.0262(7) Uani 1 1 d . . . . .
O2 O -0.1046(2) 0.3489(3) 0.2082(4) 0.0260(7) Uani 1 1 d . . . . .
N1 N 0.5092(2) 0.5394(3) 0.3559(4) 0.0152(7) Uani 1 1 d . . . . .
N2 N -0.0729(3) 0.4450(3) 0.2593(4) 0.0189(8) Uani 1 1 d . . . . .
C1 C 0.4252(3) 0.5471(3) 0.4285(5) 0.0159(8) Uani 1 1 d . . . . .
C2 C 0.5598(3) 0.6462(4) 0.2915(6) 0.0205(9) Uani 1 1 d . . . . .
H2A H 0.572933 0.705492 0.378237 0.025 Uiso 1 1 calc R U . . .
H2B H 0.521609 0.685931 0.205978 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6529(3) 0.5953(4) 0.2233(7) 0.0274(10) Uani 1 1 d . . . . .
H3A H 0.706660 0.652218 0.240818 0.033 Uiso 1 1 calc R U . . .
H3B H 0.646701 0.579283 0.106222 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6688(3) 0.4784(4) 0.3164(7) 0.0269(10) Uani 1 1 d . . . . .
H4A H 0.709372 0.421579 0.254277 0.032 Uiso 1 1 calc R U . . .
H4B H 0.699343 0.494211 0.422134 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5682(3) 0.4291(3) 0.3374(5) 0.0186(9) Uani 1 1 d . . . . .
H5A H 0.548077 0.381956 0.241693 0.022 Uiso 1 1 calc R U . . .
H5B H 0.563783 0.377169 0.434410 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2783(3) 0.4406(4) 0.6175(5) 0.0170(8) Uani 1 1 d . . . . .
H6A H 0.273271 0.381167 0.706386 0.020 Uiso 1 1 calc R U . . .
H6B H 0.288036 0.521196 0.666697 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1854(3) 0.4416(3) 0.5256(5) 0.0155(8) Uani 1 1 d . . . . .
C8 C 0.1514(3) 0.3364(3) 0.4521(5) 0.0164(8) Uani 1 1 d . . . . .
H8 H 0.187050 0.263645 0.461899 0.020 Uiso 1 1 calc R U . . .
C9 C 0.0664(3) 0.3361(3) 0.3653(5) 0.0173(8) Uani 1 1 d . . . . .
H9 H 0.043880 0.264622 0.314599 0.021 Uiso 1 1 calc R U . . .
C10 C 0.0152(3) 0.4436(4) 0.3545(5) 0.0159(8) Uani 1 1 d . . . . .
C11 C 0.0458(3) 0.5494(3) 0.4275(5) 0.0176(8) Uani 1 1 d . . . . .
H11 H 0.009344 0.621628 0.418749 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1309(3) 0.5473(3) 0.5135(5) 0.0179(8) Uani 1 1 d . . . . .
H12 H 0.152577 0.618805 0.565210 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C1 S2 C6 104.04(18) . . ?
C1 N1 C2 122.5(3) . . ?
C1 N1 C5 126.4(3) . . ?
C2 N1 C5 110.9(3) . . ?
O2 N2 O1 123.2(3) . . ?
O2 N2 C10 118.7(3) . . ?
O1 N2 C10 118.1(3) . . ?
N1 C1 S1 123.7(3) . . ?
N1 C1 S2 112.5(3) . . ?
S1 C1 S2 123.8(2) . . ?
N1 C2 C3 104.2(3) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 104.5(4) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 103.3(4) . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C4 103.3(3) . . ?
N1 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 S2 114.1(3) . . ?
C7 C6 H6A 108.7 . . ?
S2 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
S2 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C12 118.7(4) . . ?
C8 C7 C6 120.6(3) . . ?
C12 C7 C6 120.7(3) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.1(3) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 122.4(4) . . ?
C11 C10 N2 119.1(3) . . ?
C9 C10 N2 118.5(4) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.677(4) . ?
S2 C1 1.784(4) . ?
S2 C6 1.814(4) . ?
O1 N2 1.237(5) . ?
O2 N2 1.228(5) . ?
N1 C1 1.320(5) . ?
N1 C2 1.477(5) . ?
N1 C5 1.481(5) . ?
N2 C10 1.459(5) . ?
C2 C3 1.524(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.398(5) . ?
C7 C12 1.400(5) . ?
C8 C9 1.386(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9500 . ?
C12 H12 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
_geom_torsion_publ_flag
C2 N1 C1 S1 0.2(6) . . . . ?
C5 N1 C1 S1 175.6(3) . . . . ?
C2 N1 C1 S2 -179.3(3) . . . . ?
C5 N1 C1 S2 -3.8(5) . . . . ?
C6 S2 C1 N1 171.1(3) . . . . ?
C6 S2 C1 S1 -8.4(3) . . . . ?
C1 N1 C2 C3 178.8(4) . . . . ?
C5 N1 C2 C3 2.7(5) . . . . ?
N1 C2 C3 C4 -24.3(5) . . . . ?
C2 C3 C4 C5 36.7(5) . . . . ?
C1 N1 C5 C4 -155.9(4) . . . . ?
C2 N1 C5 C4 20.0(5) . . . . ?
C3 C4 C5 N1 -34.3(5) . . . . ?
C1 S2 C6 C7 91.6(3) . . . . ?
S2 C6 C7 C8 62.3(5) . . . . ?
S2 C6 C7 C12 -118.5(4) . . . . ?
C12 C7 C8 C9 1.6(6) . . . . ?
C6 C7 C8 C9 -179.2(4) . . . . ?
C7 C8 C9 C10 -0.7(6) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C8 C9 C10 N2 178.2(4) . . . . ?
O2 N2 C10 C11 -173.0(4) . . . . ?
O1 N2 C10 C11 7.8(6) . . . . ?
O2 N2 C10 C9 8.5(6) . . . . ?
O1 N2 C10 C9 -170.7(4) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
N2 C10 C11 C12 -178.2(4) . . . . ?
C10 C11 C12 C7 0.6(6) . . . . ?
C8 C7 C12 C11 -1.5(6) . . . . ?
C6 C7 C12 C11 179.2(4) . . . . ?
