#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/55/2015579.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_2015579
loop_
_publ_author_name
'Cobo, Debora'
'Quiroga, Jairo'
'Torre, José M. de la'
'Cobo, Justo'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 Three substituted (E)-3-aryl-2-(thienyl)acrylonitriles:
 isolated molecules, simple hydrogen-bonded chains and hydrogen-bonded
 sheets
;
_journal_coeditor_code           SK3037
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o550
_journal_page_last               o553
_journal_paper_doi               10.1107/S0108270106026874
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H8 Br N S'
_chemical_formula_moiety         'C13 H8 Br N S'
_chemical_formula_sum            'C13 H8 Br N S'
_chemical_formula_weight         290.17
_chemical_name_systematic
;
(E)-3-(4-bromophenyl)-2-(2-thienyl)acrylonitrile
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.877(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8557(2)
_cell_length_b                   24.0484(7)
_cell_length_c                   12.5466(4)
_cell_measurement_reflns_used    2598
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.35
_cell_volume                     1154.99(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12766
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.708
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.762
_refine_ls_extinction_coef       0.0211(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0401
_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)+(0.0320P)²+0.6935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                1983
_reflns_number_total             2598
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3037.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015579
_cod_database_fobs_code          2015579
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_type_symbol
_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_disorder_assembly
_atom_site_disorder_group
S S1 0.2321(3) 0.14823(4) 0.54665(9) 0.0221(3) Uani d P 0.798(3) A -1
C C1 0.264(6) 0.13968(19) 0.5189(9) 0.025 Uiso d PD 0.202(3) A -2
C C2 0.3661(7) 0.16218(11) 0.4236(2) 0.0207(6) Uani d D 1 . .
C C3 0.4157(13) 0.11210(18) 0.3703(4) 0.0246(6) Uani d P 0.798(3) A -1
S S3 0.4109(14) 0.10914(14) 0.3378(3) 0.025 Uiso d PD 0.202(3) A -2
C C4 0.3362(8) 0.06369(12) 0.4311(2) 0.0246(6) Uani d D 1 . .
C C5 0.2416(8) 0.07953(13) 0.5257(3) 0.0287(7) Uani d D 1 A .
C C27 0.4262(7) 0.21857(12) 0.3872(2) 0.0190(6) Uani d . 1 A .
C C271 0.5318(7) 0.22230(12) 0.2807(2) 0.0220(7) Uani d . 1 . .
N N27 0.6257(7) 0.22288(11) 0.1977(2) 0.0321(7) Uani d . 1 A .
C C17 0.4092(7) 0.26435(12) 0.4483(2) 0.0217(6) Uani d . 1 . .
C C11 0.4573(7) 0.32203(12) 0.4150(2) 0.0196(6) Uani d . 1 A .
C C12 0.3298(7) 0.34148(12) 0.3129(2) 0.0213(6) Uani d . 1 . .
C C13 0.3837(7) 0.39590(12) 0.2839(2) 0.0211(6) Uani d . 1 A .
C C14 0.5699(7) 0.43113(12) 0.3564(2) 0.0219(7) Uani d . 1 . .
Br Br14 0.66118(7) 0.504938(12) 0.31339(3) 0.02715(14) Uani d . 1 A .
C C15 0.6937(7) 0.41383(12) 0.4589(3) 0.0251(7) Uani d . 1 A .
C C16 0.6312(8) 0.35932(12) 0.4881(2) 0.0249(7) Uani d . 1 . .
H H1 0.2122 0.1629 0.5762 0.030 Uiso calc PR 0.202(3) A -2
H H3 0.4935 0.1102 0.3014 0.029 Uiso calc PR 0.798(3) A -1
H H4 0.3491 0.0263 0.4076 0.029 Uiso calc R 1 A .
H H5 0.1836 0.0535 0.5776 0.034 Uiso calc R 1 . .
H H17 0.3613 0.2587 0.5200 0.026 Uiso calc R 1 A .
H H12 0.2046 0.3170 0.2628 0.026 Uiso calc R 1 A .
H H13 0.2933 0.4090 0.2147 0.025 Uiso calc R 1 . .
H H15 0.8187 0.4387 0.5084 0.030 Uiso calc R 1 . .
H H16 0.7083 0.3472 0.5591 0.030 Uiso calc R 1 A .
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'
Br Br -0.2901 2.4595 '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_publ_flag
C5 S1 C2 92.13(15) no
C2 C1 C5 117.2(4) no
C2 C1 H1 121.4 no
C5 C1 H1 121.4 no
C3 C2 C1 98.2(4) no
C3 C2 C27 127.9(3) no
C1 C2 C27 133.9(3) no
C1 C2 S3 108.1(3) no
C27 C2 S3 118.0(2) no
C3 C2 S1 109.5(3) no
C27 C2 S1 122.6(2) no
S3 C2 S1 119.3(2) no
C2 C3 C4 113.0(4) no
C2 C3 H3 123.5 no
C4 C3 H3 123.5 no
C4 S3 C2 90.5(2) no
C5 C4 C3 109.7(3) no
C5 C4 S3 122.0(3) no
C5 C4 H4 125.2 no
C3 C4 H4 125.2 no
S3 C4 H4 112.7 no
C4 C5 C1 102.0(3) no
C4 C5 S1 115.7(2) no
C4 C5 H5 122.1 no
C1 C5 H5 135.9 no
S1 C5 H5 122.1 no
C17 C27 C271 120.9(3) no
C17 C27 C2 124.2(3) no
C271 C27 C2 114.8(2) no
N27 C271 C27 176.5(3) no
C27 C17 C11 126.5(3) no
C27 C17 H17 116.7 no
C11 C17 H17 116.7 no
C16 C11 C12 118.4(3) no
C16 C11 C17 119.2(3) no
C12 C11 C17 122.4(3) no
C13 C12 C11 120.8(3) no
C13 C12 H12 119.6 no
C11 C12 H12 119.6 no
C14 C13 C12 119.4(3) no
C14 C13 H13 120.3 no
C12 C13 H13 120.3 no
C13 C14 C15 121.5(3) no
C13 C14 Br14 119.1(2) no
C15 C14 Br14 119.4(2) no
C14 C15 C16 118.5(3) no
C14 C15 H15 120.7 no
C16 C15 H15 120.7 no
C15 C16 C11 121.2(3) no
C15 C16 H16 119.4 no
C11 C16 H16 119.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 1.674(3) no
S1 C2 1.718(3) no
C1 C2 1.411(3) no
C1 C5 1.452(3) no
C1 H1 0.95 no
C2 C3 1.402(5) no
C2 C27 1.458(4) no
C2 S3 1.691(3) no
C3 C4 1.445(5) no
C3 H3 0.95 no
S3 C4 1.652(3) no
C4 C5 1.338(4) no
C4 H4 0.95 no
C5 H5 0.95 no
C27 C17 1.347(4) no
C27 C271 1.446(4) y
C271 N27 1.143(4) y
C17 C11 1.467(4) no
C17 H17 0.95 no
C11 C16 1.396(4) no
C11 C12 1.397(4) no
C12 C13 1.381(4) no
C12 H12 0.95 no
C13 C14 1.380(4) no
C13 H13 0.95 no
C14 C15 1.382(4) no
C14 Br14 1.900(3) no
C15 C16 1.390(4) no
C15 H15 0.95 no
C16 H16 0.95 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C17 H17 N27 4_455 0.95 2.55 3.450(4) 159 y
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
C5 C1 C2 C3 -1.3(18) no
C5 C1 C2 C27 -178.3(7) no
C5 C1 C2 S3 4(2) no
C5 C1 C2 S1 176(7) no
C5 S1 C2 C3 -0.3(3) no
C5 S1 C2 C1 -3(5) no
C5 S1 C2 C27 -178.2(2) no
C5 S1 C2 S3 5.0(3) no
C1 C2 C3 C4 1.6(11) no
C27 C2 C3 C4 178.9(3) no
S3 C2 C3 C4 -154(2) no
S1 C2 C3 C4 1.1(4) no
C3 C2 S3 C4 21.0(16) no
C1 C2 S3 C4 -5.0(11) no
C27 C2 S3 C4 176.5(2) no
S1 C2 S3 C4 -6.6(4) no
C2 C3 C4 C5 -1.5(5) no
C2 C3 C4 S3 157.8(18) no
C2 S3 C4 C5 6.4(4) no
C2 S3 C4 C3 -16.7(13) no
C3 C4 C5 C1 0.6(11) no
S3 C4 C5 C1 -4.9(11) no
C3 C4 C5 S1 1.2(4) no
S3 C4 C5 S1 -4.2(4) no
C2 C1 C5 C4 0.5(19) no
C2 C1 C5 S1 -177(6) no
C2 S1 C5 C4 -0.6(3) no
C2 S1 C5 C1 2(4) no
C3 C2 C27 C17 -172.3(4) no
C1 C2 C27 C17 4.0(15) no
S1 C2 C27 C17 5.2(4) y
S3 C2 C27 C17 -178.0(3) no
C3 C2 C27 C271 3.6(5) no
C1 C2 C27 C271 179.8(15) no
S3 C2 C27 C271 -2.1(4) no
S1 C2 C27 C271 -178.9(2) no
C271 C27 C17 C11 6.2(5) no
C2 C27 C17 C11 -178.1(3) y
C27 C17 C11 C16 -142.4(3) no
C27 C17 C11 C12 38.7(4) y
C16 C11 C12 C13 1.9(4) no
C17 C11 C12 C13 -179.2(2) no
C11 C12 C13 C14 0.9(4) no
C12 C13 C14 C15 -2.4(4) no
C12 C13 C14 Br14 177.1(2) no
C13 C14 C15 C16 0.9(4) no
Br14 C14 C15 C16 -178.5(2) no
C14 C15 C16 C11 2.0(4) no
C12 C11 C16 C15 -3.4(4) no
C17 C11 C16 C15 177.7(3) no
