#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/74/2237426.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_2237426
loop_
_publ_author_name
'Zhang, Cun'
'Wu, Guo-Fan'
'Huang, Bao-Mei'
'Lu, Xiao-Quan'
_publ_section_title
;
 (Z)-4-Bromo-N-{(Z)-3-[(4-bromo-2,6-diisopropylphenyl)imino]butan-2-ylidene}-2,6-diisopropylaniline
;
_journal_coeditor_code           XU5664
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o216
_journal_paper_doi               10.1107/S160053681205194X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C28 H38 Br2 N2'
_chemical_formula_moiety         'C28 H38 Br2 N2'
_chemical_formula_sum            'C28 H38 Br2 N2'
_chemical_formula_weight         562.42
_chemical_name_systematic
;
(Z)-4-Bromo-N-{(Z)-3-[(4-bromo-2,6-
diisopropylphenyl)imino]butan-2-ylidene}-2,6-diisopropylaniline
;
_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                 104.905(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.099(3)
_cell_length_b                   12.199(4)
_cell_length_c                   13.566(5)
_cell_measurement_reflns_used    1370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.37
_cell_measurement_theta_min      2.86
_cell_volume                     1455.1(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7266
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    2.802
_exptl_absorpt_correction_T_max  0.6181
_exptl_absorpt_correction_T_min  0.5410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0524
_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)+(0.1000P)²+0.7029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                1460
_reflns_number_total             2685
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5664.cif
_cod_data_source_block           I
_cod_original_cell_volume        1455.2(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2237426
_cod_database_fobs_code          2237426
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 0.35688(8) 0.65673(6) 0.10127(7) 0.0922(4) Uani d . 1 1
C C1 0.7029(6) 0.8851(4) 0.1392(4) 0.0489(12) Uani d U 1 1
C C2 0.5759(6) 0.8270(4) 0.1476(4) 0.0533(14) Uani d . 1 1
H H2 0.5247 0.8477 0.1958 0.064 Uiso calc R 1 1
C C3 0.5254(6) 0.7392(5) 0.0851(4) 0.0539(14) Uani d . 1 1
C C4 0.5971(7) 0.7079(4) 0.0117(4) 0.0557(15) Uani d . 1 1
H H4 0.5608 0.6482 -0.0301 0.067 Uiso calc R 1 1
C C5 0.7232(7) 0.7651(4) -0.0001(5) 0.0585(14) Uani d U 1 1
C C6 0.7756(6) 0.8543(4) 0.0646(4) 0.0452(13) Uani d . 1 1
C C7 0.7611(8) 0.9814(5) 0.2083(5) 0.0662(14) Uani d U 1 1
H H7 0.8701 0.9872 0.2130 0.079 Uiso calc R 1 1
C C8 0.6907(11) 1.0865(6) 0.1624(7) 0.126(3) Uani d U 1 1
H H8A 0.7162 1.0991 0.0990 0.188 Uiso calc R 1 1
H H8B 0.7283 1.1459 0.2084 0.188 Uiso calc R 1 1
H H8C 0.5822 1.0819 0.1505 0.188 Uiso calc R 1 1
C C9 0.7469(11) 0.9636(8) 0.3149(6) 0.120(3) Uani d U 1 1
H H9A 0.8150 1.0122 0.3607 0.180 Uiso calc R 1 1
H H9B 0.7725 0.8891 0.3348 0.180 Uiso calc R 1 1
H H9C 0.6443 0.9783 0.3175 0.180 Uiso calc R 1 1
C C10 0.8059(9) 0.7265(6) -0.0773(6) 0.0804(16) Uani d U 1 1
H H10 0.8666 0.7876 -0.0923 0.096 Uiso calc R 1 1
C C11 0.9126(12) 0.6347(7) -0.0315(8) 0.132(3) Uani d U 1 1
H H11A 0.9847 0.6606 0.0287 0.199 Uiso calc R 1 1
H H11B 0.9656 0.6101 -0.0802 0.199 Uiso calc R 1 1
H H11C 0.8555 0.5750 -0.0139 0.199 Uiso calc R 1 1
C C12 0.6986(12) 0.6892(8) -0.1768(7) 0.126(3) Uani d U 1 1
H H12A 0.6336 0.6323 -0.1632 0.189 Uiso calc R 1 1
H H12B 0.7566 0.6616 -0.2214 0.189 Uiso calc R 1 1
H H12C 0.6378 0.7500 -0.2086 0.189 Uiso calc R 1 1
C C13 0.9228(6) 0.9765(4) -0.0034(4) 0.0512(14) Uani d . 1 1
C C14 0.7932(7) 1.0159(6) -0.0879(5) 0.081(2) Uani d . 1 1
H H14A 0.8104 0.9956 -0.1523 0.122 Uiso calc R 1 1
H H14B 0.7856 1.0942 -0.0843 0.122 Uiso calc R 1 1
H H14C 0.7003 0.9831 -0.0812 0.122 Uiso calc R 1 1
N N1 0.9141(5) 0.9060(3) 0.0633(3) 0.0504(11) Uani d . 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_3
_geom_angle
C2 C1 C6 . 118.8(5)
C2 C1 C7 . 120.9(5)
C6 C1 C7 . 120.2(5)
C3 C2 C1 . 120.2(5)
C3 C2 H2 . 119.9
C1 C2 H2 . 119.9
C2 C3 C4 . 121.2(5)
C2 C3 Br1 . 119.7(4)
C4 C3 Br1 . 119.0(4)
C3 C4 C5 . 120.3(5)
C3 C4 H4 . 119.8
C5 C4 H4 . 119.8
C4 C5 C6 . 118.4(5)
C4 C5 C10 . 119.8(5)
C6 C5 C10 . 121.7(5)
C1 C6 C5 . 121.1(5)
C1 C6 N1 . 118.6(5)
C5 C6 N1 . 119.9(5)
C8 C7 C9 . 113.0(7)
C8 C7 C1 . 111.3(5)
C9 C7 C1 . 112.5(5)
C8 C7 H7 . 106.5
C9 C7 H7 . 106.5
C1 C7 H7 . 106.5
C7 C8 H8A . 109.5
C7 C8 H8B . 109.5
H8A C8 H8B . 109.5
C7 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C7 C9 H9A . 109.5
C7 C9 H9B . 109.5
H9A C9 H9B . 109.5
C7 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C11 C10 C5 . 109.2(6)
C11 C10 C12 . 110.1(7)
C5 C10 C12 . 112.8(6)
C11 C10 H10 . 108.2
C5 C10 H10 . 108.2
C12 C10 H10 . 108.2
C10 C11 H11A . 109.5
C10 C11 H11B . 109.5
H11A C11 H11B . 109.5
C10 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
C10 C12 H12A . 109.5
C10 C12 H12B . 109.5
H12A C12 H12B . 109.5
C10 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
N1 C13 C14 . 125.7(5)
N1 C13 C13 3_775 116.6(6)
C14 C13 C13 3_775 117.8(6)
C13 C14 H14A . 109.5
C13 C14 H14B . 109.5
H14A C14 H14B . 109.5
C13 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
C13 N1 C6 . 122.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C3 . 1.894(5)
C1 C2 . 1.384(7)
C1 C6 . 1.396(7)
C1 C7 . 1.511(8)
C2 C3 . 1.371(7)
C2 H2 . 0.9300
C3 C4 . 1.376(8)
C4 C5 . 1.387(7)
C4 H4 . 0.9300
C5 C6 . 1.402(7)
C5 C10 . 1.513(8)
C6 N1 . 1.414(7)
C7 C8 . 1.495(10)
C7 C9 . 1.501(9)
C7 H7 . 0.9800
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 C11 . 1.507(11)
C10 C12 . 1.517(11)
C10 H10 . 0.9800
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 N1 . 1.265(6)
C13 C14 . 1.497(8)
C13 C13 3_775 1.498(10)
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
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
C6 C1 C2 C3 . 1.6(8)
C7 C1 C2 C3 . -179.3(5)
C1 C2 C3 C4 . -1.3(9)
C1 C2 C3 Br1 . 177.3(4)
C2 C3 C4 C5 . 0.2(9)
Br1 C3 C4 C5 . -178.4(4)
C3 C4 C5 C6 . 0.4(9)
C3 C4 C5 C10 . 176.9(6)
C2 C1 C6 C5 . -0.9(8)
C7 C1 C6 C5 . 180.0(5)
C2 C1 C6 N1 . -173.4(5)
C7 C1 C6 N1 . 7.5(8)
C4 C5 C6 C1 . -0.1(8)
C10 C5 C6 C1 . -176.4(6)
C4 C5 C6 N1 . 172.3(5)
C10 C5 C6 N1 . -4.1(9)
C2 C1 C7 C8 . -90.6(8)
C6 C1 C7 C8 . 88.5(8)
C2 C1 C7 C9 . 37.4(8)
C6 C1 C7 C9 . -143.5(6)
C4 C5 C10 C11 . -81.6(8)
C6 C5 C10 C11 . 94.7(8)
C4 C5 C10 C12 . 41.1(9)
C6 C5 C10 C12 . -142.6(7)
C14 C13 N1 C6 . 0.5(9)
C13 C13 N1 C6 3_775 -179.2(6)
C1 C6 N1 C13 . -106.2(6)
C5 C6 N1 C13 . 81.2(7)
