#------------------------------------------------------------------------------
#$Date: 2016-07-23 04:15:45 +0300 (Sat, 23 Jul 2016) $
#$Revision: 184624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241785.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_2241785
loop_
_publ_author_name
'Chaabene, Marwa'
'Khatyr, Abderrahim'
'Knorr, Michael'
'Askri, Moheddine'
'Rousselin, Yoann'
'Kubicki, Marek M.'
_publ_section_title
;
 Crystal structure of
 4,4-dibromo-1-(3,4-dimethoxyphenyl)-2-azabuta-1,3-diene-1-carbonitrile
;
_journal_coeditor_code           PK2582
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1167
_journal_page_last               1170
_journal_paper_doi               10.1107/S2056989016011075
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H10 Br2 N2 O2'
_chemical_formula_moiety         'C12 H10 Br2 N2 O2'
_chemical_formula_sum            'C12 H10 Br2 N2 O2'
_chemical_formula_weight         374.04
_chemical_name_systematic
;
4,4-Dibromo-1-(3,4-dimethoxyphenyl)-2-azabuta-1,3-diene-1-carbonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                106.162(2)
_cell_angle_beta                 100.887(2)
_cell_angle_gamma                110.009(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6878(4)
_cell_length_b                   9.2782(5)
_cell_length_c                   10.8111(6)
_cell_measurement_reflns_used    8732
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.527
_cell_measurement_theta_min      2.97
_cell_volume                     660.57(6)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23955
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.619
_diffrn_reflns_theta_min         2.971
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.131
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_description       plqte
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.415
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0272
_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)+(0.0307P)²+0.5386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                2442
_reflns_number_total             3045
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2582sup1.cif
_cod_data_source_block           I
_cod_database_code               2241785
_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_min   0.309
_shelx_estimated_absorpt_t_max   0.579
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_occupancy
C C1 0.5229(4) 0.2556(4) 0.9031(3) 0.0198(6) Uani d 1
H H1A 0.5402 0.1716 0.8346 0.030 Uiso calc 1
H H1B 0.3876 0.2129 0.9037 0.030 Uiso calc 1
H H1C 0.6109 0.2824 0.9927 0.030 Uiso calc 1
C C2 0.6815(5) 0.8341(4) 0.8299(3) 0.0246(7) Uani d 1
H H2A 0.7114 0.8389 0.7465 0.037 Uiso calc 1
H H2B 0.7909 0.9196 0.9088 0.037 Uiso calc 1
H H2C 0.5636 0.8527 0.8307 0.037 Uiso calc 1
C C3 0.4518(4) 0.3908(3) 0.7558(3) 0.0163(6) Uani d 1
C C4 0.3008(4) 0.2473(3) 0.6590(3) 0.0160(6) Uani d 1
H H4 0.2729 0.1450 0.6709 0.019 Uiso calc 1
C C5 0.1904(4) 0.2535(3) 0.5444(3) 0.0156(6) Uani d 1
H H5 0.0857 0.1552 0.4792 0.019 Uiso calc 1
C C6 0.2308(4) 0.4007(3) 0.5242(3) 0.0149(5) Uani d 1
C C7 0.3852(4) 0.5476(3) 0.6221(3) 0.0154(6) Uani d 1
H H7 0.4130 0.6496 0.6096 0.019 Uiso calc 1
C C8 0.4946(4) 0.5419(3) 0.7352(3) 0.0149(5) Uani d 1
C C9 0.1186(4) 0.4092(3) 0.4029(3) 0.0148(5) Uani d 1
C C10 -0.0396(4) 0.2543(4) 0.3038(3) 0.0210(6) Uani d 1
C C11 0.0555(4) 0.5495(3) 0.2655(3) 0.0175(6) Uani d 1
H H11 -0.0400 0.4495 0.1958 0.021 Uiso calc 1
C C12 0.0911(4) 0.6927(3) 0.2490(3) 0.0139(5) Uani d 1
N N1 0.1576(3) 0.5463(3) 0.3839(2) 0.0145(5) Uani d 1
N N2 -0.1661(4) 0.1374(3) 0.2229(3) 0.0356(7) Uani d 1
O O1 0.5666(3) 0.4013(2) 0.8715(2) 0.0195(4) Uani d 1
O O2 0.6500(3) 0.6752(2) 0.8351(2) 0.0195(4) Uani d 1
Br Br1 0.27146(4) 0.89631(3) 0.38235(3) 0.01976(9) Uani d 1
Br Br2 -0.04365(4) 0.69810(3) 0.08743(3) 0.01900(9) 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 0.0033 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'
O O 0.0106 0.0060 '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
H1A C1 H1B 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C1 H1A 109.5
O1 C1 H1B 109.5
O1 C1 H1C 109.5
H2A C2 H2B 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
O2 C2 H2A 109.5
O2 C2 H2B 109.5
O2 C2 H2C 109.5
C4 C3 C8 119.4(3)
O1 C3 C4 125.4(3)
O1 C3 C8 115.1(2)
C3 C4 H4 120.1
C3 C4 C5 119.8(3)
C5 C4 H4 120.1
C4 C5 H5 119.5
C6 C5 C4 120.9(3)
C6 C5 H5 119.5
C5 C6 C7 119.6(3)
C5 C6 C9 121.7(2)
C7 C6 C9 118.7(2)
C6 C7 H7 120.2
C8 C7 C6 119.6(3)
C8 C7 H7 120.2
C7 C8 C3 120.5(3)
O2 C8 C3 114.7(2)
O2 C8 C7 124.8(2)
C6 C9 C10 117.0(2)
N1 C9 C6 121.6(2)
N1 C9 C10 121.5(3)
N2 C10 C9 176.7(3)
C12 C11 H11 120.0
C12 C11 N1 120.0(3)
N1 C11 H11 120.0
C11 C12 Br1 123.0(2)
C11 C12 Br2 120.4(2)
Br1 C12 Br2 116.65(14)
C9 N1 C11 120.4(2)
C3 O1 C1 118.0(2)
C8 O2 C2 116.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C1 O1 1.431(3)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C2 O2 1.430(3)
C3 C4 1.387(4)
C3 C8 1.418(4)
C3 O1 1.345(3)
C4 H4 0.9500
C4 C5 1.391(4)
C5 H5 0.9500
C5 C6 1.383(4)
C6 C7 1.415(4)
C6 C9 1.464(4)
C7 H7 0.9500
C7 C8 1.372(4)
C8 O2 1.372(3)
C9 C10 1.465(4)
C9 N1 1.288(3)
C10 N2 1.147(4)
C11 H11 0.9500
C11 C12 1.332(4)
C11 N1 1.384(4)
C12 Br1 1.872(3)
C12 Br2 1.878(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1A Br1 1_555 1_555 2_666 0.98 3.013 3.867(4) 146.4
C1 H1B Br2 1_555 1_555 2_566 0.98 3.038 3.869(4) 143.4
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
C3 C4 C5 C6 1.1(4)
C3 C8 O2 C2 -171.0(2)
C4 C3 C8 C7 1.5(4)
C4 C3 C8 O2 -178.2(2)
C4 C3 O1 C1 -4.4(4)
C4 C5 C6 C7 -0.7(4)
C4 C5 C6 C9 178.7(3)
C5 C6 C7 C8 0.8(4)
C5 C6 C9 C10 0.3(4)
C5 C6 C9 N1 -179.5(3)
C6 C7 C8 C3 -1.2(4)
C6 C7 C8 O2 178.5(2)
C6 C9 N1 C11 176.9(2)
C7 C6 C9 C10 179.8(2)
C7 C6 C9 N1 0.0(4)
C7 C8 O2 C2 9.3(4)
C8 C3 C4 C5 -1.4(4)
C8 C3 O1 C1 175.8(2)
C9 C6 C7 C8 -178.7(2)
C10 C9 N1 C11 -2.9(4)
C12 C11 N1 C9 177.2(3)
N1 C11 C12 Br1 -1.7(4)
N1 C11 C12 Br2 179.0(2)
O1 C3 C4 C5 178.8(3)
O1 C3 C8 C7 -178.7(3)
O1 C3 C8 O2 1.5(4)

_cod_database_fobs_code 2241785
