#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/88/2218865.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_2218865
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Mirkhani, Valiollah'
'Kia, Reza'
'Vartooni, Akbar Rostami'
_publ_section_title
;
 N,N'-Bis(3-bromobenzylidene)ethane-1,2-diamine
;
_journal_coeditor_code           AT2587
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1471
_journal_paper_doi               10.1107/S1600536808021132
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H14 Br2 N2'
_chemical_formula_moiety         'C16 H14 Br2 N2'
_chemical_formula_sum            'C16 H14 Br2 N2'
_chemical_formula_weight         394.11
_chemical_name_systematic
;
N,N'-Bis(3-bromobenzylidene)ethane-1,2-diamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.5920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.25780(10)
_cell_length_b                   4.65490(10)
_cell_length_c                   25.3272(5)
_cell_measurement_reflns_used    8650
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      38.27
_cell_measurement_theta_min      3.22
_cell_volume                     736.32(2)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            24876
_diffrn_reflns_theta_full        37.49
_diffrn_reflns_theta_max         37.49
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.495
_exptl_absorpt_correction_T_max  0.3929
_exptl_absorpt_correction_T_min  0.1248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.615
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0284
_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)+(0.0244P)²+0.509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                2975
_reflns_number_total             3822
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2587.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218865
_cod_database_fobs_code          2218865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
Br Br1 0.30202(2) 0.03394(3) 0.278341(6) 0.02085(4) Uani d 1
N N1 0.35517(18) 0.8207(3) 0.44274(5) 0.0165(2) Uani d 1
C C1 0.2106(2) 0.3996(3) 0.36391(5) 0.0158(2) Uani d 1
C C2 0.1288(2) 0.1862(3) 0.33044(5) 0.0165(2) Uani d 1
C C3 -0.0766(2) 0.0762(3) 0.33433(6) 0.0188(3) Uani d 1
C C4 -0.2013(2) 0.1822(3) 0.37319(6) 0.0194(3) Uani d 1
C C5 -0.1226(2) 0.3970(3) 0.40730(6) 0.0181(2) Uani d 1
C C6 0.0838(2) 0.5062(3) 0.40303(5) 0.0158(2) Uani d 1
C C7 0.1634(2) 0.7313(3) 0.43991(6) 0.0162(2) Uani d 1
C C8 0.4077(2) 1.0477(3) 0.48093(6) 0.0171(2) Uani d 1
H H1 0.348(3) 0.476(4) 0.3617(9) 0.021(5) Uiso d 1
H H3 -0.128(3) -0.067(5) 0.3113(9) 0.026(6) Uiso d 1
H H4 -0.344(3) 0.115(5) 0.3752(8) 0.025(5) Uiso d 1
H H5 -0.207(4) 0.474(5) 0.4344(10) 0.030(6) Uiso d 1
H H7 0.064(3) 0.805(5) 0.4623(8) 0.019(5) Uiso d 1
H H8A 0.448(3) 1.212(5) 0.4612(8) 0.024(5) Uiso d 1
H H8B 0.283(3) 1.109(4) 0.5004(7) 0.014(4) Uiso d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.02520(7) 0.02173(8) 0.01584(6) 0.00015(5) 0.00296(4) -0.00294(6)
N1 0.0157(5) 0.0168(6) 0.0168(5) -0.0003(4) 0.0000(4) -0.0027(4)
C1 0.0152(5) 0.0160(6) 0.0160(5) 0.0002(4) -0.0002(4) 0.0008(5)
C2 0.0188(5) 0.0167(6) 0.0137(5) 0.0010(4) -0.0007(4) -0.0002(4)
C3 0.0206(6) 0.0168(7) 0.0183(6) -0.0013(5) -0.0037(4) -0.0018(5)
C4 0.0153(5) 0.0196(7) 0.0232(7) -0.0019(4) -0.0014(5) -0.0012(5)
C5 0.0154(5) 0.0184(7) 0.0205(6) -0.0008(4) 0.0012(4) -0.0019(5)
C6 0.0151(5) 0.0147(6) 0.0173(5) 0.0000(4) -0.0003(4) -0.0010(4)
C7 0.0154(5) 0.0162(6) 0.0170(6) 0.0007(4) 0.0001(4) -0.0015(5)
C8 0.0160(5) 0.0170(6) 0.0179(6) 0.0001(4) -0.0018(4) -0.0030(5)
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
C7 N1 C8 . . 116.70(12)
C2 C1 C6 . . 118.96(12)
C2 C1 H1 . . 122.9(13)
C6 C1 H1 . . 118.1(13)
C1 C2 C3 . . 121.90(13)
C1 C2 Br1 . . 119.28(10)
C3 C2 Br1 . . 118.81(11)
C4 C3 C2 . . 118.88(13)
C4 C3 H3 . . 121.0(14)
C2 C3 H3 . . 120.1(13)
C3 C4 C5 . . 120.27(13)
C3 C4 H4 . . 119.5(13)
C5 C4 H4 . . 120.1(13)
C4 C5 C6 . . 120.41(14)
C4 C5 H5 . . 121.6(14)
C6 C5 H5 . . 118.0(14)
C5 C6 C1 . . 119.58(13)
C5 C6 C7 . . 119.22(13)
C1 C6 C7 . . 121.20(12)
N1 C7 C6 . . 123.50(13)
N1 C7 H7 . . 120.7(12)
C6 C7 H7 . . 115.8(12)
N1 C8 C8 . 3_676 109.87(15)
N1 C8 H8A . . 106.8(12)
C8 C8 H8A 3_676 . 110.5(12)
N1 C8 H8B . . 112.9(11)
C8 C8 H8B 3_676 . 110.9(11)
H8A C8 H8B . . 105.7(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C2 . 1.8967(14)
N1 C7 . 1.2676(17)
N1 C8 . 1.4564(19)
C1 C2 . 1.383(2)
C1 C6 . 1.399(2)
C1 H1 . 0.93(2)
C2 C3 . 1.393(2)
C3 C4 . 1.385(2)
C3 H3 . 0.93(2)
C4 C5 . 1.391(2)
C4 H4 . 0.95(2)
C5 C6 . 1.3985(19)
C5 H5 . 0.96(2)
C6 C7 . 1.470(2)
C7 H7 . 0.93(2)
C8 C8 3_676 1.525(3)
C8 H8A . 0.96(2)
C8 H8B . 0.991(19)
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 . 0.5(2)
C6 C1 C2 Br1 . -178.55(10)
C1 C2 C3 C4 . -0.6(2)
Br1 C2 C3 C4 . 178.42(11)
C2 C3 C4 C5 . 0.7(2)
C3 C4 C5 C6 . -0.6(2)
C4 C5 C6 C1 . 0.5(2)
C4 C5 C6 C7 . -179.45(14)
C2 C1 C6 C5 . -0.4(2)
C2 C1 C6 C7 . 179.52(13)
C8 N1 C7 C6 . 179.20(13)
C5 C6 C7 N1 . 172.14(14)
C1 C6 C7 N1 . -7.8(2)
C7 N1 C8 C8 3_676 123.51(16)
