#------------------------------------------------------------------------------
#$Date: 2021-05-25 03:53:24 +0300 (Tue, 25 May 2021) $
#$Revision: 265471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/28/1562835.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_1562835
loop_
_publ_author_name
'Bhide, Malavika'
'Mears, Kristian Luke'
'Carmalt, Claire J.'
'Knapp, Caroline E.'
_publ_section_title
;
 Synthesis, solution dynamics and chemical vapour deposition of
 heteroleptic zinc complexes via ethyl and amide zinc thioureides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01846A
_journal_year                    2021
_chemical_formula_moiety         'C9 H12 N2 S'
_chemical_formula_sum            'C9 H12 N2 S'
_chemical_formula_weight         180.27
_chemical_name_systematic        xstr1192
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-16
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-03-19 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.114(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.63230(10)
_cell_length_b                   13.4731(2)
_cell_length_c                   12.4161(3)
_cell_measurement_reflns_used    9412
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.3440
_cell_measurement_theta_min      4.8410
_cell_volume                     927.55(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  -6.00   1.00    1.00    --  -42.75 125.00  60.00   39
  2  ω    -81.00  -8.00   1.00    1.00    --  -42.75 125.00 150.00   73
  3  ω   -100.00 -15.00   1.00    1.00    --  -42.75 -57.00-150.00   85
  4  ω   -113.00 -16.00   1.00    1.00    --  -42.75 -57.00 -60.00   97
  5  ω    -49.00 -15.00   1.00    1.00    --  -42.75 -57.00  90.00   34
  6  ω   -101.00 -18.00   1.00    1.00    --  -42.75 -38.00   0.00   83
  7  ω   -109.00 -53.00   1.00    1.00    --  -42.75 -57.00-180.00   56
  8  ω    -78.00 -51.00   1.00    1.00    --  -42.75 -57.00  90.00   27
  9  ω    -57.00  31.00   1.00    1.00    --  -42.75  38.00 -30.00   88
 10  ω    -86.00 -10.00   1.00    1.00    --  -42.75 125.00 -30.00   76
 11  ω     11.00  42.00   1.00    1.00    --   42.75  79.00 -32.47   31
 12  ω     10.00  41.00   1.00    1.00    --   42.75  76.00-109.07   31
 13  ω     13.00  41.00   1.00    1.00    --   42.75  79.00 167.10   28
 14  ω      9.00  36.00   1.00    1.00    --   42.75  82.00  55.66   27
 15  ω      9.00  35.00   1.00    1.00    --   42.75  82.00 135.34   26
 16  ω    108.00 137.00   1.00    1.00    --  104.49 -77.00  90.00   29
 17  ω     29.00  88.00   1.00    1.00    --  104.49 -77.00  90.00   59
 18  ω     76.00 102.00   1.00    1.00    --  104.49  58.00-128.50   26
 19  ω     75.00 102.00   1.00    1.00    --  104.49  61.00 120.00   27
 20  ω     31.00 113.00   1.00    1.00    --  104.49-125.00  90.00   82
 21  ω     32.00  99.00   1.00    1.00    --  104.49-125.00  30.00   67
 22  ω     75.00 101.00   1.00    1.00    --  104.49  63.00 -68.00   26
 23  ω    113.00 175.00   1.00    1.00    --  104.49  61.00 -30.00   62
 24  ω     75.00 175.00   1.00    1.00    --  104.49  61.00 -90.00  100
 25  ω     75.00 108.00   1.00    1.00    --  104.49  61.00 -30.00   33
 26  ω     31.00 113.00   1.00    1.00    --  104.49-125.00 -60.00   82
 27  ω     31.00 110.00   1.00    1.00    --  104.49-125.00-150.00   79
 28  ω    115.00 162.00   1.00    1.00    --  104.49 125.00  60.00   47
 29  ω     75.00 156.00   1.00    1.00    --  104.49  61.00-120.00   81
 30  ω     75.00 105.00   1.00    1.00    --  104.49  61.00-180.00   30
 31  ω     77.00 106.00   1.00    1.00    --  104.49  61.00   6.04   29
 32  ω     80.00 162.00   1.00    1.00    --  104.49  37.00  49.96   82
 33  ω     76.00 106.00   1.00    1.00    --  104.49  63.00-170.62   30
 34  ω     75.00 102.00   1.00    1.00    --  104.49  61.00  30.00   27
 35  ω     75.00 173.00   1.00    1.00    --  104.49  61.00  90.00   98
 36  ω     74.00 101.00   1.00    1.00    --  104.49  66.00  45.91   27
 37  ω     75.00 101.00   1.00    1.00    --  104.49  61.00   0.00   26
 38  ω    135.00 177.00   1.00    1.00    --  104.49  61.00   0.00   42
 39  ω     79.00 106.00   1.00    1.00    --  104.49  45.00   0.00   27
 40  ω     83.00 109.00   1.00    1.00    --  104.49  45.00  90.00   26
 41  ω     86.00 117.00   1.00    1.00    --  104.49  45.00 150.00   31
 42  ω     76.00 173.00   1.00    1.00    --  104.49  61.00 150.00   97
 43  ω     80.00 107.00   1.00    1.00    --  104.49  45.00 -30.00   27
 44  ω     78.00 105.00   1.00    1.00    --  104.49  61.00  60.00   27
 45  ω     76.00 137.00   1.00    1.00    --  104.49  61.00-150.00   61
 46  ω    145.00 172.00   1.00    1.00    --  104.49  58.00-128.50   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0766084000
_diffrn_orient_matrix_UB_12      0.1071817000
_diffrn_orient_matrix_UB_13      0.0203136000
_diffrn_orient_matrix_UB_21      -0.2601412000
_diffrn_orient_matrix_UB_22      -0.0242275000
_diffrn_orient_matrix_UB_23      -0.0554986000
_diffrn_orient_matrix_UB_31      -0.0604341000
_diffrn_orient_matrix_UB_32      -0.0316292000
_diffrn_orient_matrix_UB_33      0.1113205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.694
_diffrn_reflns_theta_min         4.885
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_preparation       'PhSCN + HNMe2'
_exptl_crystal_recrystallization_method
'Crystallised from a toluene/THF solution'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0329
_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)+(0.0512P)²+0.4834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1736
_reflns_number_total             1823
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc01846a2.cif
_cod_data_source_block           xstr1192
_cod_database_code               1562835
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C9 H12 N2 S '
_chemical_oxdiff_usercomment     'CEK MAB'
_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_max   0.879
_shelx_estimated_absorpt_t_min   0.620
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C9(H9), C6(H6), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_olex2_date_sample_data_collection 2020-03-10
_olex2_exptl_crystal_mounting_method 'Nylon loop'
_olex2_submission_original_sample_id xstr1192
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.022
_oxdiff_exptl_absorpt_empirical_full_min 0.735
loop_
_space_group_symop_operation_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_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 1.02553(6) 0.28813(3) 0.39936(3) 0.02347(14) Uani 1 1 d . . . . .
N1 N 0.7634(2) 0.25772(9) 0.55473(10) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.6313(2) 0.38407(9) 0.43609(10) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.5191 0.3919 0.4742 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6306(3) 0.44837(10) 0.34521(12) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.7974(2) 0.31053(10) 0.46751(11) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.8250(3) 0.51009(11) 0.33793(12) 0.0225(3) Uani 1 1 d . . . . .
H5 H 0.9615 0.5090 0.3923 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4247(3) 0.45222(11) 0.26493(12) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.2933 0.4119 0.2704 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8142(3) 0.57328(11) 0.24909(13) 0.0248(3) Uani 1 1 d . . . . .
H6 H 0.9448 0.6141 0.2438 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6101(3) 0.57636(12) 0.16777(13) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.6046 0.6184 0.1080 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5842(3) 0.28483(12) 0.62163(13) 0.0270(3) Uani 1 1 d . . . . .
H3A H 0.5808 0.3557 0.6294 0.041 Uiso 1 1 calc R U . . .
H3B H 0.6259 0.2548 0.6925 0.041 Uiso 1 1 calc R U . . .
H3C H 0.4281 0.2618 0.5869 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4154(3) 0.51622(12) 0.17676(13) 0.0285(3) Uani 1 1 d . . . . .
H8 H 0.2773 0.5187 0.1233 0.034 Uiso 1 1 calc R U . . .
C2 C 0.9032(3) 0.16844(12) 0.58863(13) 0.0297(4) Uani 1 1 d . . . . .
H2A H 0.9770 0.1451 0.5293 0.045 Uiso 1 1 calc R U . . .
H2B H 0.7986 0.1180 0.6085 0.045 Uiso 1 1 calc R U . . .
H2C H 1.0262 0.1835 0.6504 0.045 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'
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 N1 C3 122.59(12) . . ?
C1 N1 C2 121.69(12) . . ?
C2 N1 C3 115.71(12) . . ?
C4 N2 H2 117.5 . . ?
C1 N2 H2 117.5 . . ?
C1 N2 C4 124.93(12) . . ?
C5 C4 N2 121.55(13) . . ?
C5 C4 C9 119.87(13) . . ?
C9 C4 N2 118.51(13) . . ?
N1 C1 S1 122.79(11) . . ?
N1 C1 N2 115.29(13) . . ?
N2 C1 S1 121.92(11) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.58(13) . . ?
C6 C5 H5 120.2 . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 119.99(14) . . ?
C8 C9 H9 120.0 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.76(14) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.31(14) . . ?
C8 C7 H7 120.3 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.47(14) . . ?
C7 C8 H8 119.8 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
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 1.6852(15) . ?
N1 C1 1.3374(19) . ?
N1 C3 1.4617(19) . ?
N1 C2 1.4588(19) . ?
N2 H2 0.8600 . ?
N2 C4 1.4219(18) . ?
N2 C1 1.3715(18) . ?
C4 C5 1.391(2) . ?
C4 C9 1.391(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.387(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C8 H8 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
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
N2 C4 C5 C6 -178.48(13) . . . . ?
N2 C4 C9 C8 178.18(14) . . . . ?
C4 N2 C1 S1 0.1(2) . . . . ?
C4 N2 C1 N1 -179.24(13) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C4 C9 C8 C7 0.1(2) . . . . ?
C1 N2 C4 C5 -59.5(2) . . . . ?
C1 N2 C4 C9 123.59(15) . . . . ?
C5 C4 C9 C8 1.2(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C9 C4 C5 C6 -1.6(2) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
C3 N1 C1 S1 172.27(11) . . . . ?
C3 N1 C1 N2 -8.4(2) . . . . ?
C2 N1 C1 S1 -8.1(2) . . . . ?
C2 N1 C1 N2 171.14(13) . . . . ?
