#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/43/2204332.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204332
loop_
_publ_author_name
'Homrighausen, Craig L.'
'Krause Bauer, Jeanette A.'
_publ_section_title
;
 2-(4-Chlorophenyl)-4,4-bis(methylsulfanyl)-1,3-butadiene-1,1-dicarbonitrile
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1828
_journal_page_last               o1829
_journal_paper_doi               10.1107/S1600536804022986
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C14 H11 Cl N2 S2'
_chemical_formula_moiety         'C14 H11 Cl N2 S2'
_chemical_formula_sum            'C14 H11 Cl N2 S2'
_chemical_formula_weight         306.82
_chemical_name_systematic
;
2-(4-Chlorophenyl)-4,4-bis(methylsulfanyl)-1,3-butadiene-1,1-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXTL v5.03'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1633(18)
_cell_length_b                   11.836(2)
_cell_length_c                   13.911(3)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      5.0
_cell_volume                     1492.6(5)
_computing_cell_refinement       P3/P4-PC
_computing_data_collection       'P3/P4-PC (Siemens, 1989)'
_computing_data_reduction        'XDISK (Siemens, 1989)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P3'
_diffrn_measurement_method       θ--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3649
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.6
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.52
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0365P)²+0.6836P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.102
_reflns_number_gt                2345
_reflns_number_total             3442
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er6001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204332
_cod_database_fobs_code          2204332
loop_
_symmetry_equiv_pos_as_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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.26745(10) 0.97560(7) 0.49461(5) 0.0814(3) Uani d . 1 Cl
S1 0.12018(8) 0.87710(6) 0.10780(5) 0.05283(18) Uani d . 1 S
S2 0.14420(9) 0.84396(6) -0.09845(5) 0.0594(2) Uani d . 1 S
N1 0.5335(3) 1.3189(2) 0.19990(17) 0.0707(7) Uani d . 1 N
N2 0.4318(3) 1.2400(2) -0.10914(17) 0.0644(6) Uani d . 1 N
C1 0.2917(3) 1.0080(2) 0.37617(16) 0.0487(6) Uani d . 1 C
C2 0.2142(3) 1.0966(2) 0.33022(18) 0.0512(6) Uani d . 1 C
H2 0.1490 1.1380 0.3617 0.061 Uiso calc R 1 H
C3 0.2345(3) 1.12338(19) 0.23643(17) 0.0456(5) Uani d . 1 C
H3 0.1849 1.1849 0.2054 0.055 Uiso calc R 1 H
C4 0.3274(2) 1.05992(17) 0.18836(15) 0.0379(5) Uani d . 1 C
C5 0.4049(3) 0.97193(19) 0.23698(17) 0.0459(5) Uani d . 1 C
H5 0.4690 0.9293 0.2055 0.055 Uiso calc R 1 H
C6 0.3886(3) 0.9464(2) 0.33146(17) 0.0501(6) Uani d . 1 C
H6 0.4428 0.8880 0.3643 0.060 Uiso calc R 1 H
C7 0.3433(2) 1.08571(18) 0.08595(15) 0.0393(5) Uani d . 1 C
C8 0.4130(3) 1.18447(18) 0.06690(16) 0.0424(5) Uani d . 1 C
C9 0.2899(3) 1.01202(19) 0.00832(15) 0.0432(5) Uani d . 1 C
H9 0.3235 1.0272 -0.0503 0.052 Uiso calc R 1 H
C10 0.4782(3) 1.2594(2) 0.14157(18) 0.0496(6) Uani d . 1 C
C11 0.4253(3) 1.2169(2) -0.03036(19) 0.0483(6) Uani d . 1 C
C12 0.1962(3) 0.92205(19) 0.00705(16) 0.0424(5) Uani d . 1 C
C13 -0.0076(3) 0.7681(2) 0.06349(19) 0.0587(7) Uani d . 1 C
H13A -0.0539 0.7393 0.1161 0.088 Uiso calc R 1 H
H13B 0.0440 0.7081 0.0365 0.088 Uiso calc R 1 H
H13C -0.0814 0.7985 0.0142 0.088 Uiso calc R 1 H
C14 0.2045(3) 0.9234(2) -0.19412(17) 0.0651(8) Uani d . 1 C
H14A 0.1785 0.8840 -0.2545 0.098 Uiso calc R 1 H
H14B 0.3096 0.9327 -0.1812 0.098 Uiso calc R 1 H
H14C 0.1579 0.9962 -0.1982 0.098 Uiso calc R 1 H
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'
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_publ_flag
C12 S1 C13 105.20(12) ?
C12 S2 C14 105.84(12) ?
C6 C1 C2 121.5(2) ?
C6 C1 Cl1 119.65(19) ?
C2 C1 Cl1 118.8(2) ?
C1 C2 C3 118.9(2) ?
C1 C2 H2 120.5 ?
C3 C2 H2 120.5 ?
C4 C3 C2 120.7(2) ?
C4 C3 H3 119.6 ?
C2 C3 H3 119.6 ?
C3 C4 C5 118.9(2) ?
C3 C4 C7 120.5(2) ?
C5 C4 C7 120.6(2) ?
C6 C5 C4 120.9(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
C1 C6 C5 119.0(2) ?
C1 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
C8 C7 C9 119.6(2) ?
C8 C7 C4 118.21(19) ?
C9 C7 C4 122.19(19) ?
C7 C8 C11 121.0(2) ?
C7 C8 C10 122.9(2) ?
C11 C8 C10 116.1(2) ?
C12 C9 C7 129.5(2) ?
C12 C9 H9 115.3 ?
C7 C9 H9 115.3 ?
N1 C10 C8 178.1(3) y
N2 C11 C8 177.7(3) y
C9 C12 S1 123.60(18) ?
C9 C12 S2 121.26(18) ?
S1 C12 S2 115.13(13) ?
S1 C13 H13A 109.5 ?
S1 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
S1 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
S2 C14 H14A 109.5 ?
S2 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
S2 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.737(2) ?
S1 C12 1.737(2) y
S1 C13 1.790(3) y
S2 C12 1.741(2) ?
S2 C14 1.782(3) ?
N1 C10 1.136(3) y
N2 C11 1.140(3) y
C1 C6 1.368(3) ?
C1 C2 1.371(3) ?
C2 C3 1.381(3) ?
C2 H2 0.9300 ?
C3 C4 1.380(3) ?
C3 H3 0.9300 ?
C4 C5 1.381(3) ?
C4 C7 1.485(3) y
C5 C6 1.378(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.376(3) y
C7 C9 1.419(3) y
C8 C11 1.427(3) y
C8 C10 1.429(3) y
C9 C12 1.366(3) y
C9 H9 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 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_publ_flag
C6 C1 C2 C3 0.3(4) ?
Cl1 C1 C2 C3 0.72(18) ?
C1 C2 C3 C4 2.1(4) ?
C2 C3 C4 C5 2.7(3) ?
C2 C3 C4 C7 2.9(2) ?
C3 C4 C5 C6 0.9(3) ?
C7 C4 C5 C6 1.1(2) ?
C2 C1 C6 C5 2.1(4) ?
Cl1 C1 C6 C5 1.03(18) ?
C4 C5 C6 C1 1.4(4) ?
C3 C4 C7 C8 69.0(3) ?
C5 C4 C7 C8 68.8(2) ?
C3 C4 C7 C9 68.7(3) ?
C5 C4 C7 C9 68.5(3) ?
C9 C7 C8 C11 3.4(3) ?
C4 C7 C8 C11 3.1(2) ?
C9 C7 C8 C10 4.2(2) y
C4 C7 C8 C10 3.9(3) ?
C8 C7 C9 C12 13.0(2) y
C4 C7 C9 C12 13.3(4) ?
C7 C8 C10 N1 53(9) ?
C7 C8 C11 N2 13(7) ?
C7 C9 C12 S1 0.4(4) y
C7 C9 C12 S2 0.65(19) ?
C13 S1 C12 C9 6.1(2) ?
C13 S1 C12 S2 5.88(17) ?
C14 S2 C12 C9 11.5(2) ?
C14 S2 C12 S1 11.69(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2006741
