#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228621.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_2228621
loop_
_publ_author_name
'Kang, Tai-Ran'
_publ_section_title
;
 2-[(E)-4-(2-Bromophenyl)but-3-en-2-ylidene]malononitrile
;
_journal_coeditor_code           XU5097
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3365
_journal_paper_doi               10.1107/S1600536810049536
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 Br N2'
_chemical_formula_moiety         'C13 H9 Br N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13
_chemical_name_common
;
2-[(E)-4-(2-Bromophenyl)but-3-en-2-ylidene]malononitrile
;
_chemical_name_systematic
;
2-[(E)-4-(2-Bromophenyl)but-3-en-2-ylidene]propanedinitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.192(6)
_cell_angle_beta                 76.628(8)
_cell_angle_gamma                66.038(9)
_cell_formula_units_Z            2
_cell_length_a                   7.0353(7)
_cell_length_b                   7.0765(5)
_cell_length_c                   13.3229(8)
_cell_measurement_reflns_used    3664
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.9063
_cell_measurement_theta_min      6.8336
_cell_volume                     589.03(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED(Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 7.9575
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Sapphire3 Gemini ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4500
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         6.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.523
_exptl_absorpt_correction_T_max  0.4099
_exptl_absorpt_correction_T_min  0.2928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.550
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.0933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                1923
_reflns_number_total             2062
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5097.cif
_cod_data_source_block           I
_cod_original_cell_volume        589.03(8)
_cod_database_code               2228621
_cod_database_fobs_code          2228621
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br Br1 0.67339(5) 0.15902(4) 0.54256(2) 0.06643(19) Uani d . 1 . .
C C8 0.8775(4) -0.3609(4) 0.7789(2) 0.0493(6) Uani d . 1 . .
H H8 0.8557 -0.3515 0.8499 0.059 Uiso calc R 1 . .
N N2 1.2571(5) -1.0939(4) 0.7188(2) 0.0735(8) Uani d . 1 . .
C C11 1.0519(4) -0.7373(4) 0.7984(2) 0.0455(5) Uani d . 1 . .
C C4 0.5298(5) 0.2647(5) 0.8955(2) 0.0598(7) Uani d . 1 . .
H H4 0.4994 0.2887 0.9655 0.072 Uiso calc R 1 . .
C C13 1.0087(4) -0.7342(4) 0.9092(2) 0.0527(6) Uani d . 1 . .
C C5 0.6402(5) 0.0655(4) 0.8620(2) 0.0563(6) Uani d . 1 . .
H H5 0.6835 -0.0433 0.9103 0.068 Uiso calc R 1 . .
C C9 0.9905(4) -0.5636(4) 0.7362(2) 0.0461(5) Uani d . 1 . .
C C7 0.8037(4) -0.1879(4) 0.7217(2) 0.0516(6) Uani d . 1 . .
H H7 0.8277 -0.2024 0.6510 0.062 Uiso calc R 1 . .
C C2 0.5107(4) 0.3937(4) 0.7208(3) 0.0563(7) Uani d . 1 . .
H H2 0.4684 0.5041 0.6732 0.068 Uiso calc R 1 . .
C C10 1.0389(5) -0.5797(5) 0.6211(2) 0.0584(7) Uani d . 1 . .
H H10A 1.1160 -0.7222 0.6044 0.088 Uiso calc R 1 . .
H H10B 1.1228 -0.5013 0.5895 0.088 Uiso calc R 1 . .
H H10C 0.9087 -0.5260 0.5958 0.088 Uiso calc R 1 . .
C C6 0.6889(4) 0.0226(4) 0.7573(2) 0.0478(6) Uani d . 1 . .
N N1 0.9737(5) -0.7329(5) 0.9974(2) 0.0749(8) Uani d . 1 . .
C C3 0.4644(4) 0.4289(4) 0.8242(3) 0.0604(7) Uani d . 1 . .
H H3 0.3891 0.5629 0.8466 0.072 Uiso calc R 1 . .
C C12 1.1667(4) -0.9376(4) 0.7555(2) 0.0532(6) Uani d . 1 . .
C C1 0.6206(4) 0.1936(4) 0.6873(2) 0.0496(6) Uani d . 1 . .
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'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 C8 C9 . . 123.3(3) ?
C7 C8 H8 . . 118.4 ?
C9 C8 H8 . . 118.4 ?
C9 C11 C12 . . 120.8(2) ?
C9 C11 C13 . . 123.1(2) ?
C12 C11 C13 . . 116.1(2) ?
C5 C4 C3 . . 119.7(3) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
N1 C13 C11 . . 179.5(3) ?
C4 C5 C6 . . 121.9(3) ?
C4 C5 H5 . . 119.0 ?
C6 C5 H5 . . 119.0 ?
C11 C9 C8 . . 121.1(2) ?
C11 C9 C10 . . 120.0(2) ?
C8 C9 C10 . . 119.0(2) ?
C8 C7 C6 . . 127.4(3) ?
C8 C7 H7 . . 116.3 ?
C6 C7 H7 . . 116.3 ?
C3 C2 C1 . . 120.0(3) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C5 C6 C1 . . 116.6(2) ?
C5 C6 C7 . . 122.1(2) ?
C1 C6 C7 . . 121.3(3) ?
C2 C3 C4 . . 120.2(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
N2 C12 C11 . . 178.1(3) ?
C2 C1 C6 . . 121.5(3) ?
C2 C1 Br1 . . 117.1(2) ?
C6 C1 Br1 . . 121.4(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.908(3) ?
C8 C7 . 1.327(4) ?
C8 C9 . 1.449(4) ?
C8 H8 . 0.9300 ?
N2 C12 . 1.140(4) ?
C11 C9 . 1.358(4) ?
C11 C12 . 1.437(4) ?
C11 C13 . 1.438(4) ?
C4 C5 . 1.383(4) ?
C4 C3 . 1.390(5) ?
C4 H4 . 0.9300 ?
C13 N1 . 1.144(4) ?
C5 C6 . 1.401(4) ?
C5 H5 . 0.9300 ?
C9 C10 . 1.502(4) ?
C7 C6 . 1.461(4) ?
C7 H7 . 0.9300 ?
C2 C3 . 1.373(5) ?
C2 C1 . 1.387(4) ?
C2 H2 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C6 C1 . 1.412(4) ?
C3 H3 . 0.9300 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C11 C13 N1 . . . . 13E1(4) ?
C12 C11 C13 N1 . . . . -5E1(5) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C12 C11 C9 C8 . . . . -179.0(2) ?
C13 C11 C9 C8 . . . . 0.7(4) ?
C12 C11 C9 C10 . . . . 1.1(4) ?
C13 C11 C9 C10 . . . . -179.1(3) ?
C7 C8 C9 C11 . . . . -176.0(3) ?
C7 C8 C9 C10 . . . . 3.8(4) ?
C9 C8 C7 C6 . . . . -179.9(3) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
C4 C5 C6 C7 . . . . -179.4(3) ?
C8 C7 C6 C5 . . . . -0.8(5) ?
C8 C7 C6 C1 . . . . 179.5(3) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C5 C4 C3 C2 . . . . -0.5(5) ?
C9 C11 C12 N2 . . . . -6(10) ?
C13 C11 C12 N2 . . . . 175(10) ?
C3 C2 C1 C6 . . . . -0.6(4) ?
C3 C2 C1 Br1 . . . . 178.9(2) ?
C5 C6 C1 C2 . . . . 0.0(4) ?
C7 C6 C1 C2 . . . . 179.7(3) ?
C5 C6 C1 Br1 . . . . -179.5(2) ?
C7 C6 C1 Br1 . . . . 0.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656405
