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#$Date: 2021-03-05 03:43:07 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262554 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/21/7242131.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_7242131
loop_
_publ_author_name
'Tan, Sang Loon'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Non-covalent interactions involving remote substituents influence the
 topologies of supramolecular chains featuring
 hydroxyl-O--H⋯O(hydroxyl) hydrogen bonding in crystals of
 (HOCH2CH2)2NC(S)N(H)(C6H4Y-4) for Y = H, Me, Cl and NO2
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1723
_journal_page_last               1743
_journal_paper_doi               10.1039/D0CE01810D
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C11 H15 Cl N2 O2 S'
_chemical_formula_sum            'C11 H15 Cl N2 O2 S'
_chemical_formula_weight         274.76
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-29 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.221(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1366(2)
_cell_length_b                   10.7767(3)
_cell_length_c                   16.6259(4)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2652
_cell_measurement_theta_min      2.6983
_cell_volume                     1258.39(6)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4685
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        74.933
_diffrn_reflns_theta_max         74.933
_diffrn_reflns_theta_min         4.914
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0308
_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)+(0.0398P)²+0.2198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2243
_reflns_number_total             2554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01810d2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7242130--7242133.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7242131
_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   0.573
_shelx_estimated_absorpt_t_max   0.818
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
Cl1 Cl 0.80245(6) 0.59295(4) 0.47362(3) 0.02599(12) Uani 1 1 d . . . . .
S1 S 0.13297(5) 0.64270(4) 0.13426(2) 0.01620(11) Uani 1 1 d . . . . .
O1 O -0.15441(17) 0.92972(12) 0.30553(8) 0.0240(3) Uani 1 1 d D . . . .
H1O H -0.180(3) 0.958(2) 0.3492(9) 0.036 Uiso 1 1 d D U . . .
O2 O -0.26300(17) 0.52693(11) 0.05416(8) 0.0195(3) Uani 1 1 d D . . . .
H2O H -0.1480(15) 0.544(2) 0.0634(13) 0.029 Uiso 1 1 d D U . . .
N1 N 0.05327(19) 0.72513(14) 0.27682(8) 0.0172(3) Uani 1 1 d D . . . .
H1N H -0.004(3) 0.7849(14) 0.2993(11) 0.021 Uiso 1 1 d D U . . .
N2 N -0.19119(18) 0.73888(12) 0.16804(8) 0.0132(3) Uani 1 1 d . . . . .
C1 C -0.0088(2) 0.70438(14) 0.19580(10) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.2332(2) 0.69068(15) 0.32209(9) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.2987(2) 0.56889(15) 0.32485(10) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.223863 0.506315 0.294262 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4728(2) 0.53854(16) 0.37206(11) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.518225 0.455553 0.373733 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5801(2) 0.63075(16) 0.41686(10) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.5162(2) 0.75170(16) 0.41644(10) 0.0162(3) Uani 1 1 d . . . . .
H6 H 0.590218 0.813474 0.448237 0.019 Uiso 1 1 calc R U . . .
C7 C 0.3416(2) 0.78163(15) 0.36864(9) 0.0159(3) Uani 1 1 d . . . . .
H7 H 0.295876 0.864512 0.367721 0.019 Uiso 1 1 calc R U . . .
C8 C -0.3272(2) 0.76749(16) 0.22264(10) 0.0160(3) Uani 1 1 d . . . . .
H8A H -0.297522 0.714467 0.271885 0.019 Uiso 1 1 calc R U . . .
H8B H -0.457067 0.745975 0.194308 0.019 Uiso 1 1 calc R U . . .
C9 C -0.3255(2) 0.90244(16) 0.24936(10) 0.0184(3) Uani 1 1 d . . . . .
H9A H -0.334752 0.957028 0.200921 0.022 Uiso 1 1 calc R U . . .
H9B H -0.437057 0.918841 0.275684 0.022 Uiso 1 1 calc R U . . .
C10 C -0.2666(2) 0.75086(15) 0.08015(9) 0.0146(3) Uani 1 1 d . . . . .
H10A H -0.159341 0.765499 0.050865 0.018 Uiso 1 1 calc R U . . .
H10B H -0.351316 0.824189 0.071287 0.018 Uiso 1 1 calc R U . . .
C11 C -0.3766(2) 0.63750(15) 0.04398(10) 0.0171(3) Uani 1 1 d . . . . .
H11A H -0.488947 0.625879 0.070602 0.020 Uiso 1 1 calc R U . . .
H11B H -0.423125 0.651626 -0.015020 0.020 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'
Cl Cl 0.3639 0.7018 '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
C9 O1 H1O 110.6(17) . . ?
C11 O2 H2O 110.7(16) . . ?
C1 N1 C2 126.00(14) . . ?
C1 N1 H1N 116.6(13) . . ?
C2 N1 H1N 114.2(13) . . ?
C1 N2 C10 121.54(13) . . ?
C1 N2 C8 123.07(13) . . ?
C10 N2 C8 115.39(12) . . ?
N2 C1 N1 114.64(14) . . ?
N2 C1 S1 122.83(12) . . ?
N1 C1 S1 122.52(12) . . ?
C3 C2 C7 119.65(15) . . ?
C3 C2 N1 122.14(15) . . ?
C7 C2 N1 118.11(15) . . ?
C4 C3 C2 120.24(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.25(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.56(15) . . ?
C6 C5 Cl1 119.41(13) . . ?
C4 C5 Cl1 119.03(13) . . ?
C5 C6 C7 118.88(15) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 120.40(15) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N2 C8 C9 114.09(14) . . ?
N2 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O1 C9 C8 110.42(13) . . ?
O1 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 113.29(13) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O2 C11 C10 112.34(13) . . ?
O2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
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
Cl1 C5 1.7448(17) . ?
S1 C1 1.6968(16) . ?
O1 C9 1.430(2) . ?
O1 H1O 0.836(9) . ?
O2 C11 1.434(2) . ?
O2 H2O 0.829(9) . ?
N1 C1 1.360(2) . ?
N1 C2 1.418(2) . ?
N1 H1N 0.880(9) . ?
N2 C1 1.354(2) . ?
N2 C10 1.4705(19) . ?
N2 C8 1.4743(19) . ?
C2 C3 1.391(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
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
C10 N2 C1 N1 165.29(14) . . . . ?
C8 N2 C1 N1 -14.4(2) . . . . ?
C10 N2 C1 S1 -13.6(2) . . . . ?
C8 N2 C1 S1 166.73(12) . . . . ?
C2 N1 C1 N2 175.81(15) . . . . ?
C2 N1 C1 S1 -5.3(2) . . . . ?
C1 N1 C2 C3 -55.6(2) . . . . ?
C1 N1 C2 C7 128.01(17) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
N1 C2 C3 C4 -177.84(15) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 Cl1 -178.00(13) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
Cl1 C5 C6 C7 177.75(12) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C3 C2 C7 C6 1.3(2) . . . . ?
N1 C2 C7 C6 177.74(14) . . . . ?
C1 N2 C8 C9 88.74(18) . . . . ?
C10 N2 C8 C9 -90.96(16) . . . . ?
N2 C8 C9 O1 -71.15(17) . . . . ?
C1 N2 C10 C11 97.77(17) . . . . ?
C8 N2 C10 C11 -82.53(17) . . . . ?
N2 C10 C11 O2 -58.80(18) . . . . ?
