#------------------------------------------------------------------------------
#$Date: 2022-03-07 12:08:27 +0200 (Mon, 07 Mar 2022) $
#$Revision: 273499 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104671.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_8104671
loop_
_publ_author_name
'Manana, Pholani'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 4-chloro-thiophenol, C6H5ClS
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1079
_journal_page_last               1081
_journal_paper_doi               10.1515/ncrs-2021-0225
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C6 H5 Cl S'
_chemical_formula_sum            'C6 H5 Cl S'
_chemical_formula_weight         144.61
_chemical_name_common            4-chloro-thiophenol
_chemical_name_systematic        4-chloro-thiophenol
_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   difmap
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.869(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7461(2)
_cell_length_b                   9.7601(4)
_cell_length_c                   5.7466(3)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.56
_cell_volume                     320.59(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2752
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         4.131
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0216
_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)+(0.018200P)²+0.084200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0545
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                740
_reflns_number_total             795
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL aa016c_a.res in P2(1)/n
    aa016c.res
    created by SHELXL-2018/3 at 13:18:37 on 27-Apr-2021
REM Old TITL aa016c_na2_P21n in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.100, Rweak 0.002, Alpha 0.006
REM <I/s>   0.361 for   44 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C3 Cl
CELL  0.71073   5.7461   9.7601   5.7466   90.000   95.869   90.000
ZERR    2.000   0.0002   0.0004   0.0003    0.000    0.002    0.000
LATT  1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C H S CL
UNIT 12 10 2 2

EQIV $2 x+1/2, -y+3/2, z+1/2
EQIV $3 x-1/2, -y+3/2, z-1/2

HTAB S1 S1_$2
HTAB S1 S1_$3

ACTA NOHKL
BOND $H
CONF
FMAP 2
HTAB
L.S. 100
LIST 4
PLAN -20
SIZE 0.164 0.327 0.548
TEMP 23.000

REM WGHT 0.018200 0.084200
REM WGHT 0.018200 0.084200
REM WGHT 0.018200 0.084200
WGHT    0.018200    0.084200
FVAR       0.64040
C1    1    0.375926    0.590882    0.624101    11.00000    0.02847    0.02358 =
         0.02904    0.00088    0.00748   -0.00061
C2    1    0.281137    0.545654    0.405790    11.00000    0.02573    0.03132 =
         0.03052    0.00248    0.00208    0.00106
AFIX  43
H2    2    0.134751    0.576427    0.343306    11.00000   -1.20000
AFIX   0
C3    1    0.405709    0.454326    0.281152    11.00000    0.02963    0.03152 =
         0.02613   -0.00118    0.00216   -0.00245
AFIX  43
H3    2    0.343171    0.423547    0.134799    11.00000   -1.20000
AFIX   0
PART 1
CL1   4    0.218015    0.705834    0.782062    10.50000    0.02699    0.02849 =
         0.02681   -0.00658    0.00424    0.00731

PART 2
S1    3    0.217258    0.705849    0.782605    10.50000    0.05759    0.05029 =
         0.06021   -0.01186    0.01275    0.01028
H1A   2    0.353815    0.724450    0.941710    10.25000    0.03736
H1B   2    0.043520    0.716429    0.661485    10.25000    0.02975
HKLF 4




REM  aa016c_a.res in P2(1)/n
REM wR2 = 0.0545, GooF = S = 1.218, Restrained GooF = 1.218 for all data
REM R1 = 0.0216 for 740 Fo > 4sig(Fo) and 0.0231 for all 795 data
REM 54 parameters refined using 0 restraints

END  
     
WGHT      0.0182      0.0842 

REM Instructions for potential hydrogen bonds
HTAB S1 S1_$2
HTAB S1 S1_$3

REM Highest difference peak  0.257,  deepest hole -0.189,  1-sigma level  0.039
Q1    1   0.5002  0.5798  0.6453  11.00000  0.05    0.26
Q2    1   0.3498  0.5802  0.5005  11.00000  0.05    0.25
Q3    1   0.4692  0.5536  0.6709  11.00000  0.05    0.24
Q4    1   0.3641  0.4991  0.3577  11.00000  0.05    0.24
Q5    1   0.3197  0.6139  0.6734  11.00000  0.05    0.13
Q6    1   0.0264  0.6511  0.7235  11.00000  0.05    0.10
Q7    1   0.3961  0.7619  0.8521  11.00000  0.05    0.09
Q8    1   0.2957  0.6645  0.9836  11.00000  0.05    0.08
Q9    1   0.1080  0.7469  0.6005  11.00000  0.05    0.08
Q10   1   0.0378  0.5471  0.9601  11.00000  0.05    0.08
Q11   1   0.0767  0.4827  0.8751  11.00000  0.05    0.08
Q12   1   0.5963  0.5468  0.7882  11.00000  0.05    0.07
Q13   1  -0.0736  0.5935  0.9592  11.00000  0.05    0.07
Q14   1   0.4288  0.7853  0.7890  11.00000  0.05    0.07
Q15   1   0.2093  0.7923  0.6064  11.00000  0.05    0.07
Q16   1   0.2192  0.8304  0.6194  11.00000  0.05    0.07
Q17   1   0.0080  0.5594  0.2718  11.00000  0.05    0.07
Q18   1   0.2580  0.3772  0.1517  11.00000  0.05    0.06
Q19   1   0.0266  0.6706  0.8567  11.00000  0.05    0.06
Q20   1  -0.0422  0.6586  1.0305  11.00000  0.05    0.06
;
_cod_data_source_file            suppl_j_ncrs-2021-0225_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104671
_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   0.668
_shelx_estimated_absorpt_t_max   0.880
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 0.37593(19) 0.59088(10) 0.62410(19) 0.0267(2) Uani 1 1 d . . . . .
C2 C 0.28114(19) 0.54565(11) 0.40579(19) 0.0292(3) Uani 1 1 d . . . . .
H2 H 0.134751 0.576427 0.343306 0.035 Uiso 1 1 calc R U . . .
C3 C 0.40571(19) 0.45433(11) 0.28115(19) 0.0291(3) Uani 1 1 d . . . . .
H3 H 0.343171 0.423547 0.134799 0.035 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2180(4) 0.7058(2) 0.7821(3) 0.0273(5) Uani 0.5 1 d . . P A 1
S1 S 0.2173(7) 0.7058(4) 0.7826(6) 0.0556(13) Uani 0.5 1 d . . P A 2
H1A H 0.354(12) 0.724(6) 0.942(12) 0.037(15) Uiso 0.25 1 d . . P B 2
H1B H 0.044(11) 0.716(6) 0.661(11) 0.030(14) Uiso 0.25 1 d . . P C 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0285(5) 0.0236(5) 0.0290(5) 0.0009(4) 0.0075(4) -0.0006(4)
C2 0.0257(5) 0.0313(5) 0.0305(5) 0.0025(4) 0.0021(4) 0.0011(4)
C3 0.0296(5) 0.0315(5) 0.0261(5) -0.0012(4) 0.0022(4) -0.0024(4)
Cl1 0.0270(10) 0.0285(12) 0.0268(9) -0.0066(8) 0.0042(7) 0.0073(8)
S1 0.058(2) 0.050(2) 0.060(2) -0.0119(15) 0.0128(16) 0.0103(16)
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'
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
C2 C1 C3 120.61(10) . 3_666
C2 C1 Cl1 119.70(11) . .
C3 C1 Cl1 119.69(11) 3_666 .
C2 C1 S1 119.68(15) . .
C3 C1 S1 119.72(15) 3_666 .
C3 C2 C1 119.71(10) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C2 C3 C1 119.69(10) . 3_666
C2 C3 H3 120.2 . .
C1 C3 H3 120.2 3_666 .
C1 S1 H1A 99(3) . .
C1 S1 H1B 102(3) . .
H1A S1 H1B 159(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3877(16) .
C1 C3 1.3877(16) 3_666
C1 Cl1 1.753(2) .
C1 S1 1.758(4) .
C2 C3 1.3874(15) .
C2 H2 0.9300 .
C3 H3 0.9300 .
S1 H1A 1.16(8) .
S1 H1B 1.16(7) .
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
S1^b H1A^b S1^b 1.16(8) 2.80(7) 3.9452(16) 172(4) 4_676
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
C3 C1 C2 C3 0.05(17) 3_666 . . .
Cl1 C1 C2 C3 -179.77(11) . . . .
S1 C1 C2 C3 -179.64(16) . . . .
C1 C2 C3 C1 -0.05(17) . . . 3_666
