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#$Date: 2022-11-21 10:13:03 +0200 (Mon, 21 Nov 2022) $
#$Revision: 279420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106172.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_8106172
loop_
_publ_author_name
'Tao, Lu'
'Xu-Liang, Nie'
'Zhong-Chao, Li'
'Ping, Lin'
'Xin-Chen, Shang-guan'
'Zhong-Ping, Yin'
'Da-Yong, Peng'
_publ_section_title
;
 Crystal structure of
 2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione,
 C14H15Cl2N3OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              427
_journal_page_last               429
_journal_paper_doi               10.1515/ncrs-2017-0328
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C14 H14 Cl2 N3 O S'
_chemical_formula_sum            'C14 H14 Cl2 N3 O S'
_chemical_formula_weight         344.25
_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
_cell_angle_alpha                90
_cell_angle_beta                 92.7020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9215(8)
_cell_length_b                   9.5992(7)
_cell_length_c                   16.5801(13)
_cell_measurement_reflns_used    8920
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.34
_cell_volume                     1577.3(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0170
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11684
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         2.345
_exptl_absorpt_coefficient_mu    0.545
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             712.0
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0094(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0344P)²+0.6146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2656
_reflns_number_total             2936
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0328_suppl.cif
_cod_data_source_block           3112_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106172
_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   0.693
_shelx_estimated_absorpt_t_max   0.723
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
C1 C 0.7323(2) 0.66482(17) 0.61436(10) 0.0516(4) Uani 1 1 d . . . . .
H1 H 0.6794 0.7376 0.5935 0.062 Uiso 1 1 calc R U . . .
C2 C 0.84031(14) 0.53053(14) 0.70284(9) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.92735(15) 0.36509(15) 0.60076(9) 0.0361(3) Uani 1 1 d . . . . .
H3A H 0.9895 0.3362 0.6445 0.043 Uiso 1 1 calc R U . . .
H3B H 0.9804 0.3911 0.5554 0.043 Uiso 1 1 calc R U . . .
C4 C 0.83687(15) 0.24171(15) 0.57598(8) 0.0329(3) Uani 1 1 d . . . . .
C5 C 0.92447(16) 0.11124(15) 0.56248(9) 0.0381(3) Uani 1 1 d . . . . .
H5A H 0.8649 0.0354 0.5457 0.046 Uiso 1 1 calc R U . . .
H5B H 0.9821 0.1305 0.5181 0.046 Uiso 1 1 calc R U . . .
C6 C 1.01250(15) 0.06181(15) 0.63334(9) 0.0347(3) Uani 1 1 d . . . . .
C7 C 0.96042(17) -0.02691(17) 0.69042(11) 0.0457(4) Uani 1 1 d . . . . .
H7 H 0.8705 -0.0539 0.6842 0.055 Uiso 1 1 calc R U . . .
C8 C 1.0371(2) -0.0763(2) 0.75583(12) 0.0591(5) Uani 1 1 d . . . . .
H8 H 0.9989 -0.1356 0.7928 0.071 Uiso 1 1 calc R U . . .
C9 C 1.1700(2) -0.0377(2) 0.76620(12) 0.0640(5) Uani 1 1 d . . . . .
H9 H 1.2217 -0.0693 0.8107 0.077 Uiso 1 1 calc R U . . .
C10 C 1.22629(19) 0.0479(2) 0.71047(12) 0.0563(5) Uani 1 1 d . . . . .
H10 H 1.3165 0.0738 0.7169 0.068 Uiso 1 1 calc R U . . .
C11 C 1.14863(15) 0.09504(16) 0.64506(9) 0.0397(3) Uani 1 1 d . . . . .
C12 C 0.75051(17) 0.26781(17) 0.49824(10) 0.0431(4) Uani 1 1 d . . . . .
C13 C 0.61365(19) 0.3310(2) 0.49738(13) 0.0613(5) Uani 1 1 d . . . . .
H13A H 0.5885 0.3944 0.4537 0.074 Uiso 1 1 calc R U . . .
H13B H 0.5769 0.3541 0.5489 0.074 Uiso 1 1 calc R U . . .
C14 C 0.6296(2) 0.1794(2) 0.47708(13) 0.0633(5) Uani 1 1 d . . . . .
H14A H 0.6028 0.1113 0.5164 0.076 Uiso 1 1 calc R U . . .
H14B H 0.6144 0.1517 0.4211 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl 1.22774(5) 0.19811(5) 0.57459(3) 0.05949(15) Uani 1 1 d . . . . .
Cl2 Cl 0.84950(6) 0.31206(6) 0.41537(3) 0.06604(17) Uani 1 1 d . . . . .
N1 N 0.76161(14) 0.64550(13) 0.69401(8) 0.0401(3) Uani 1 1 d . . . . .
N2 N 0.78618(17) 0.57066(14) 0.57046(8) 0.0518(4) Uani 1 1 d . . . . .
N3 N 0.85275(13) 0.48627(12) 0.62649(7) 0.0365(3) Uani 1 1 d . . . . .
O1 O 0.75012(11) 0.22343(11) 0.64115(6) 0.0385(2) Uani 1 1 d . . . . .
H1A H 0.7121 0.1478 0.6367 0.058 Uiso 1 1 calc R U . . .
S1 S 0.90906(4) 0.46187(4) 0.78907(2) 0.03918(12) Uani 1 1 d . . . . .
H2 H 0.7362(18) 0.6930(19) 0.7305(11) 0.043(5) 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'
O O 0.0106 0.0060 '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
N2 C1 N1 112.26(15) . .
N3 C2 N1 103.49(12) . .
N3 C2 S1 128.43(11) . .
N1 C2 S1 128.07(11) . .
N3 C3 C4 113.43(12) . .
O1 C4 C3 105.05(11) . .
O1 C4 C12 108.91(12) . .
C3 C4 C12 113.36(13) . .
O1 C4 C5 111.96(12) . .
C3 C4 C5 109.81(12) . .
C12 C4 C5 107.82(12) . .
C6 C5 C4 116.81(12) . .
C7 C6 C11 115.74(14) . .
C7 C6 C5 120.20(14) . .
C11 C6 C5 124.01(14) . .
C8 C7 C6 122.48(16) . .
C9 C8 C7 119.77(17) . .
C8 C9 C10 119.72(17) . .
C9 C10 C11 119.73(17) . .
C10 C11 C6 122.52(16) . .
C10 C11 Cl1 117.46(13) . .
C6 C11 Cl1 120.01(12) . .
C13 C12 C14 60.51(13) . .
C13 C12 C4 123.25(15) . .
C14 C12 C4 120.93(15) . .
C13 C12 Cl2 115.63(13) . .
C14 C12 Cl2 114.83(13) . .
C4 C12 Cl2 112.42(11) . .
C12 C13 C14 60.09(12) . .
C12 C14 C13 59.40(12) . .
C1 N1 C2 108.26(13) . .
C1 N2 N3 103.26(13) . .
C2 N3 N2 112.72(12) . .
C2 N3 C3 126.80(12) . .
N2 N3 C3 120.48(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.292(2) .
C1 N1 1.352(2) .
C2 N3 1.3464(18) .
C2 N1 1.3558(19) .
C2 S1 1.6888(15) .
C3 N3 1.4536(18) .
C3 C4 1.531(2) .
C4 O1 1.4236(17) .
C4 C12 1.534(2) .
C4 C5 1.5468(19) .
C5 C6 1.507(2) .
C6 C7 1.391(2) .
C6 C11 1.393(2) .
C7 C8 1.379(3) .
C8 C9 1.373(3) .
C9 C10 1.375(3) .
C10 C11 1.377(2) .
C11 Cl1 1.7455(16) .
C12 C13 1.487(2) .
C12 C14 1.497(3) .
C12 Cl2 1.7777(17) .
C13 C14 1.503(3) .
N2 N3 1.3775(18) .
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 H2 S1 0.807(19) 2.966(18) 3.4948(14) 125.2(15) 2_656
N1 H2 O1 0.807(19) 2.146(19) 2.8413(17) 144.3(17) 2_656
O1 H1A S1 0.82 2.51 3.2107(11) 144.7 2_646
C10 H10 S1 0.93 2.93 3.7105(19) 142.0 2_746
C5 H5B Cl1 0.97 2.65 3.1196(17) 110.1 .
C5 H5B Cl1 0.97 2.65 3.1196(17) 110.1 .
C10 H10 S1 0.93 2.93 3.7105(19) 142.0 2_746
O1 H1A S1 0.82 2.51 3.2107(11) 144.7 2_646
N1 H2 O1 0.807(19) 2.146(19) 2.8413(17) 144.3(17) 2_656
N1 H2 S1 0.807(19) 2.966(18) 3.4948(14) 125.2(15) 2_656
