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#$Date: 2022-07-04 12:21:41 +0300 (Mon, 04 Jul 2022) $
#$Revision: 276532 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105632.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_8105632
loop_
_publ_author_name
'Al-Sehemi, Abdullah G.'
'Pannipara, Mehboobali'
'Asiri, Abdullah M.'
'Arshad, Muhammad Nadeem'
'Kalam, Abul'
_publ_section_title
;
 The crystal structure of
 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              327
_journal_page_last               328
_journal_paper_doi               10.1515/ncrs-2018-0379
_journal_volume                  234
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C9 H6 N2 S'
_chemical_formula_sum            'C9 H6 N2 S'
_chemical_formula_weight         174.22
_chemical_name_common
;
[(3-Methylthiophen-2-yl)methylidene]propanedinitrile
;
_chemical_name_systematic
;
[(3-Methylthiophen-2-yl)methylidene]propanedinitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                86.522(11)
_cell_angle_beta                 87.209(10)
_cell_angle_gamma                80.673(10)
_cell_formula_units_Z            2
_cell_length_a                   3.9497(4)
_cell_length_b                   9.0268(13)
_cell_length_c                   12.2935(16)
_cell_measurement_reflns_used    1122
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.0992
_cell_measurement_theta_min      2.8966
_cell_volume                     431.37(10)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    'ORTEP [4] and PLATON [5]'
_computing_structure_refinement  'SHELXL-2016/16 (Sheldrick, 2015)[3]'
_computing_structure_solution    'SHELXL-2016/16 (Sheldrick, 2015)[2]'
_diffrn_ambient_temperature      296(3)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3141
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.133
_diffrn_reflns_theta_min         2.900
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0496
_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)+(0.015P)²+3.2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1432
_reflns_number_total             2002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0379_suppl.cif
_cod_data_source_block           exp_1115
_cod_database_code               8105632
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.8402(5) 0.1934(3) 0.76250(17) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.7663(6) 0.3487(3) 0.74636(18) 0.0457(6) Uani 1 1 d . . . . .
C3 C 0.5738(6) 0.4145(3) 0.8356(2) 0.0573(7) Uani 1 1 d . . . . .
H3 H 0.499989 0.517416 0.838691 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5069(7) 0.3136(3) 0.9160(2) 0.0599(7) Uani 1 1 d . . . . .
H4 H 0.382893 0.339822 0.980138 0.072 Uiso 1 1 calc R U . . .
C5 C 1.0300(5) 0.0960(3) 0.68699(17) 0.0417(5) Uani 1 1 d . . . . .
H5 H 1.115141 0.144226 0.625061 0.050 Uiso 1 1 calc R U . . .
C6 C 1.1072(5) -0.0561(3) 0.69057(17) 0.0418(5) Uani 1 1 d . . . . .
C7 C 1.3052(6) -0.1318(3) 0.60350(19) 0.0478(6) Uani 1 1 d . . . . .
C8 C 0.9981(6) -0.1540(3) 0.7767(2) 0.0517(6) Uani 1 1 d . . . . .
C9 C 0.8726(7) 0.4370(3) 0.6469(2) 0.0596(7) Uani 1 1 d . . . . .
H9A H 1.088037 0.387309 0.617444 0.089 Uiso 1 1 calc R U . . .
H9B H 0.896778 0.536081 0.666167 0.089 Uiso 1 1 calc R U . . .
H9C H 0.701171 0.444003 0.593236 0.089 Uiso 1 1 calc R U . . .
N1 N 1.4635(6) -0.1930(3) 0.53487(19) 0.0657(6) Uani 1 1 d . . . . .
N2 N 0.9128(7) -0.2348(3) 0.8435(2) 0.0810(8) Uani 1 1 d . . . . .
S1 S 0.67250(16) 0.13381(8) 0.88799(5) 0.0529(2) Uani 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'
S S 0.1246 0.1234 '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 C5 124.6(2) . .
C2 C1 S1 111.12(17) . .
C5 C1 S1 124.31(18) . .
C1 C2 C3 111.4(2) . .
C1 C2 C9 125.0(2) . .
C3 C2 C9 123.6(2) . .
C2 C3 H3 123.3 . .
C4 C3 C2 113.4(3) . .
C4 C3 H3 123.3 . .
C3 C4 H4 123.5 . .
C3 C4 S1 113.0(2) . .
S1 C4 H4 123.5 . .
C1 C5 H5 114.8 . .
C6 C5 C1 130.4(2) . .
C6 C5 H5 114.8 . .
C5 C6 C7 120.8(2) . .
C5 C6 C8 124.7(2) . .
C8 C6 C7 114.6(2) . .
N1 C7 C6 179.5(3) . .
N2 C8 C6 178.3(3) . .
C2 C9 H9A 109.5 . .
C2 C9 H9B 109.5 . .
C2 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C4 S1 C1 91.05(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.389(3) .
C1 C5 1.420(3) .
C1 S1 1.739(2) .
C2 C3 1.409(3) .
C2 C9 1.499(3) .
C3 H3 0.9300 .
C3 C4 1.349(4) .
C4 H4 0.9300 .
C4 S1 1.698(3) .
C5 H5 0.9300 .
C5 C6 1.356(3) .
C6 C7 1.435(3) .
C6 C8 1.433(3) .
C7 N1 1.140(3) .
C8 N2 1.140(3) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
C4 H4 N2 0.93 2.61 3.413(4) 144.4 2_657
C5 H5 N1 0.93 2.58 3.457(3) 158.1 2_856
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
C1 C2 C3 C4 0.4(3) . . . .
C1 C5 C6 C7 179.9(2) . . . .
C1 C5 C6 C8 1.3(4) . . . .
C2 C1 C5 C6 -176.9(2) . . . .
C2 C1 S1 C4 0.39(18) . . . .
C2 C3 C4 S1 -0.1(3) . . . .
C3 C4 S1 C1 -0.2(2) . . . .
C5 C1 C2 C3 179.9(2) . . . .
C5 C1 C2 C9 0.5(4) . . . .
C5 C1 S1 C4 179.9(2) . . . .
C9 C2 C3 C4 179.9(2) . . . .
S1 C1 C2 C3 -0.5(3) . . . .
S1 C1 C2 C9 -179.97(19) . . . .
S1 C1 C5 C6 3.6(4) . . . .
