#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240327.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_2240327
loop_
_publ_author_name
'Hauptvogel, Ines'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Crystal structure of 4,4'-(ethane-1,2-diyl)bis(2,6-dibromoaniline)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              97
_journal_page_last               99
_journal_paper_doi               10.1107/S2056989014027182
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H12 Br4 N2'
_chemical_formula_moiety         'C14 H12 Br4 N2'
_chemical_formula_sum            'C14 H12 Br4 N2'
_chemical_formula_weight         527.86
_chemical_name_common
;
4,4'-Diamino-3,3',5,5'-tetrabromobibenzyl
;
_chemical_name_systematic
;
4,4'-(Ethane-1,2-diyl)bis(2,6-dibromoaniline)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.706(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1219(4)
_cell_length_b                   4.4962(2)
_cell_length_c                   21.5327(9)
_cell_measurement_reflns_used    3117
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.59
_cell_volume                     780.94(6)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6211
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    10.297
_exptl_absorpt_correction_T_max  0.4930
_exptl_absorpt_correction_T_min  0.1482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1356
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0228
_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)+(0.0287P)²+0.4643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0573
_reflns_number_gt                1213
_reflns_number_total             1356
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5742sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        780.95(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2240327
_cod_database_fobs_code          2240327
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_symmetry_multiplicity
Br Br1 0.57978(4) 0.36821(8) 0.225361(14) 0.03020(13) Uani d . 1 1
Br Br2 -0.06304(4) 0.52607(9) 0.094219(15) 0.03690(14) Uani d . 1 1
N N1 0.2009(3) 0.2907(7) 0.19806(11) 0.0243(6) Uani d D 1 1
H H1A 0.260(3) 0.140(5) 0.2143(13) 0.020(9) Uiso d D 1 1
H H1B 0.102(2) 0.223(8) 0.1841(14) 0.033(9) Uiso d D 1 1
C C1 0.3975(4) 0.8813(7) 0.07282(13) 0.0216(7) Uani d . 1 1
C C2 0.4981(3) 0.7477(7) 0.12150(13) 0.0221(7) Uani d . 1 1
H H2 0.6107 0.7920 0.1274 0.026 Uiso calc R 1 1
C C3 0.4334(3) 0.5501(7) 0.16131(13) 0.0203(7) Uani d . 1 1
C C4 0.2654(3) 0.4736(7) 0.15549(12) 0.0190(7) Uani d . 1 1
C C5 0.1679(3) 0.6141(7) 0.10623(13) 0.0210(7) Uani d . 1 1
C C6 0.2309(4) 0.8108(7) 0.06593(13) 0.0222(7) Uani d . 1 1
H H6 0.1604 0.8969 0.0338 0.027 Uiso calc R 1 1
C C7 0.4705(4) 1.0862(8) 0.02740(14) 0.0279(7) Uani d . 1 1
H H7A 0.5633 1.1936 0.0493 0.034 Uiso calc R 1 1
H H7B 0.3875 1.2306 0.0113 0.034 Uiso calc R 1 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'
N N 0.0061 0.0033 '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'
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
C4 N1 H1A . . 119.6(19)
C4 N1 H1B . . 113(2)
H1A N1 H1B . . 108(3)
C6 C1 C2 . . 117.7(3)
C6 C1 C7 . . 121.5(3)
C2 C1 C7 . . 120.7(3)
C3 C2 C1 . . 120.9(3)
C3 C2 H2 . . 119.5
C1 C2 H2 . . 119.5
C2 C3 C4 . . 122.8(3)
C2 C3 Br1 . . 118.5(2)
C4 C3 Br1 . . 118.8(2)
N1 C4 C3 . . 122.0(3)
N1 C4 C5 . . 123.2(3)
C3 C4 C5 . . 114.7(3)
C6 C5 C4 . . 123.3(3)
C6 C5 Br2 . . 118.6(2)
C4 C5 Br2 . . 118.1(2)
C5 C6 C1 . . 120.7(3)
C5 C6 H6 . . 119.7
C1 C6 H6 . . 119.7
C1 C7 C7 . 3_675 111.7(4)
C1 C7 H7A . . 109.3
C7 C7 H7A 3_675 . 109.3
C1 C7 H7B . . 109.3
C7 C7 H7B 3_675 . 109.3
H7A C7 H7B . . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C3 . 1.898(3)
Br2 C5 . 1.905(3)
N1 C4 . 1.380(4)
N1 H1A . 0.877(10)
N1 H1B . 0.879(10)
C1 C6 . 1.381(4)
C1 C2 . 1.388(4)
C1 C7 . 1.514(4)
C2 C3 . 1.381(4)
C2 H2 . 0.9300
C3 C4 . 1.398(4)
C4 C5 . 1.398(4)
C5 C6 . 1.378(4)
C6 H6 . 0.9300
C7 C7 3_675 1.535(6)
C7 H7A . 0.9700
C7 H7B . 0.9700
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
N1 H1A N1 2_545 0.88(2) 2.45(3) 3.206(4) 145(2)
N1 H1B Br1 2_545 0.88(2) 3.03(3) 3.521(4) 117(2)
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_4
_geom_torsion
C6 C1 C2 C3 . 0.4(4)
C7 C1 C2 C3 . -177.0(3)
C1 C2 C3 C4 . -0.2(5)
C1 C2 C3 Br1 . 178.3(2)
C2 C3 C4 N1 . -175.7(3)
Br1 C3 C4 N1 . 5.8(4)
C2 C3 C4 C5 . -0.2(4)
Br1 C3 C4 C5 . -178.7(2)
N1 C4 C5 C6 . 176.0(3)
C3 C4 C5 C6 . 0.5(4)
N1 C4 C5 Br2 . -4.4(4)
C3 C4 C5 Br2 . -179.9(2)
C4 C5 C6 C1 . -0.4(5)
Br2 C5 C6 C1 . 180.0(2)
C2 C1 C6 C5 . -0.1(4)
C7 C1 C6 C5 . 177.3(3)
C6 C1 C7 C7 3_675 -89.9(4)
C2 C1 C7 C7 3_675 87.4(4)
