#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238666.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_2238666
loop_
_publ_author_name
'Huang, Lina'
'Du, Zhengyin'
'Liu, Wei'
'Che, Fushou'
_publ_section_title
;
 4,6-Dibromo-N-{3-[(4,6-dibromo-2,3-dimethylphenyl)imino]butan-2-ylidene}-2,3-dimethylaniline
;
_journal_coeditor_code           RK2409
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1496
_journal_paper_doi               10.1107/S1600536813023921
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C20 H20 Br4 N2'
_chemical_formula_moiety         'C20 H20 Br4 N2'
_chemical_formula_sum            'C20 H20 Br4 N2'
_chemical_formula_weight         607.98
_chemical_name_systematic
4,6-Dibromo-N-{3-[(4,6-dibromo-2,3-dimethylphenyl)imino]butan-2-ylidene}-2,3-dimethylaniline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.782(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.5582(6)
_cell_length_b                   12.8881(15)
_cell_length_c                   14.8377(11)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.3940
_cell_measurement_theta_min      3.3990
_cell_volume                     1050.43(19)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2013)'
_computing_molecular_graphics
'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_solution
'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9324
_diffrn_measured_fraction_theta_max 0.9943
_diffrn_measurement_device_type  'Agilent SuperNova (Dual, Cu at zero, Eos)'
_diffrn_measurement_method       ω--scans
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4675
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         4.57
_exptl_absorpt_coefficient_mu    9.398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.704
_refine_diff_density_min         -1.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0442
_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)+(0.0802P)²+2.2115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                1777
_reflns_number_total             1921
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            rk2409.cif
_cod_data_source_block           I
_cod_database_code               2238666
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 Br2 0.84461(11) 0.31214(5) 0.68427(4) 0.0431(2) Uani d . 1 1
N N1 0.5517(8) 0.5134(4) 0.6182(3) 0.0327(9) Uani d . 1 1
C C2 0.2754(9) 0.4881(4) 0.8311(3) 0.0269(9) Uani d . 1 1
C C3 0.6169(9) 0.3862(4) 0.7425(3) 0.0277(10) Uani d . 1 1
C C4 0.4939(9) 0.4723(4) 0.7012(3) 0.0275(10) Uani d . 1 1
C C5 0.3261(10) 0.5238(4) 0.7464(3) 0.0296(10) Uani d . 1 1
C C6 0.4633(10) 0.4739(4) 0.5417(3) 0.0341(11) Uani d . 1 1
C C7 0.5762(9) 0.3504(4) 0.8271(3) 0.0293(10) Uani d . 1 1
H H7 0.6616 0.2939 0.8548 0.035 Uiso calc R 1 1
C C1 0.1862(10) 0.6189(4) 0.7022(3) 0.0341(11) Uani d . 1 1
H H1A 0.0200 0.5999 0.6813 0.051 Uiso calc R 1 1
H H1B 0.2604 0.6422 0.6515 0.051 Uiso calc R 1 1
H H1C 0.1912 0.6736 0.7463 0.051 Uiso calc R 1 1
C C8 0.2980(12) 0.3814(5) 0.5268(3) 0.0438(14) Uani d . 1 1
H H8A 0.1479 0.4010 0.4898 0.066 Uiso calc R 1 1
H H8B 0.2654 0.3560 0.5845 0.066 Uiso calc R 1 1
H H8C 0.3751 0.3278 0.4964 0.066 Uiso calc R 1 1
C C9 0.0867(10) 0.5414(4) 0.8773(4) 0.0378(12) Uani d . 1 1
H H9A 0.1616 0.5968 0.9148 0.057 Uiso calc R 1 1
H H9B 0.0170 0.4924 0.9146 0.057 Uiso calc R 1 1
H H9C -0.0388 0.5691 0.8321 0.057 Uiso calc R 1 1
C C10 0.4039(9) 0.4017(4) 0.8689(3) 0.0277(10) Uani d . 1 1
Br Br1 0.34078(11) 0.34478(4) 0.98167(3) 0.0379(2) 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 0.0181 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_3
_geom_angle
C6 N1 C4 . 121.1(4)
C5 C2 C9 . 120.5(5)
C10 C2 C5 . 117.4(4)
C10 C2 C9 . 122.1(4)
C4 C3 Br2 . 121.1(3)
C7 C3 Br2 . 117.2(4)
C7 C3 C4 . 121.6(4)
C3 C4 N1 . 121.1(4)
C3 C4 C5 . 119.1(4)
C5 C4 N1 . 119.6(4)
C2 C5 C1 . 118.9(5)
C4 C5 C2 . 120.9(4)
C4 C5 C1 . 120.2(4)
N1 C6 C6 3_666 115.8(6)
N1 C6 C8 . 126.4(4)
C8 C6 C6 3_666 117.8(5)
C3 C7 H7 . 121.1
C10 C7 C3 . 117.8(5)
C10 C7 H7 . 121.1
C5 C1 H1A . 109.5
C5 C1 H1B . 109.5
C5 C1 H1C . 109.5
H1A C1 H1B . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C6 C8 H8A . 109.5
C6 C8 H8B . 109.5
C6 C8 H8C . 109.5
H8A C8 H8B . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C2 C9 H9A . 109.5
C2 C9 H9B . 109.5
C2 C9 H9C . 109.5
H9A C9 H9B . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C2 C10 Br1 . 120.6(4)
C7 C10 C2 . 123.2(4)
C7 C10 Br1 . 116.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br2 C3 . 1.895(5)
N1 C4 . 1.422(6)
N1 C6 . 1.273(6)
C2 C5 . 1.406(6)
C2 C9 . 1.504(7)
C2 C10 . 1.395(7)
C3 C4 . 1.395(7)
C3 C7 . 1.388(6)
C4 C5 . 1.397(7)
C5 C1 . 1.543(7)
C6 C6 3_666 1.518(9)
C6 C8 . 1.501(7)
C7 H7 . 0.9300
C7 C10 . 1.385(7)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
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 Br1 . 1.908(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_site_symmetry_4
_geom_torsion
Br2 C3 C4 N1 . -6.1(6)
Br2 C3 C4 C5 . 179.4(3)
Br2 C3 C7 C10 . -177.8(4)
N1 C4 C5 C2 . -176.5(4)
N1 C4 C5 C1 . 5.7(7)
C3 C4 C5 C2 . -1.9(7)
C3 C4 C5 C1 . -179.7(4)
C3 C7 C10 C2 . -1.5(7)
C3 C7 C10 Br1 . 176.5(4)
C4 N1 C6 C6 3_666 179.2(6)
C4 N1 C6 C8 . -1.5(10)
C4 C3 C7 C10 . 1.5(7)
C5 C2 C10 C7 . -0.1(7)
C5 C2 C10 Br1 . -178.0(4)
C6 N1 C4 C3 . 82.4(7)
C6 N1 C4 C5 . -103.1(6)
C7 C3 C4 N1 . 174.7(4)
C7 C3 C4 C5 . 0.2(7)
C9 C2 C5 C4 . -177.4(5)
C9 C2 C5 C1 . 0.4(7)
C9 C2 C10 C7 . 179.1(5)
C9 C2 C10 Br1 . 1.2(7)
C10 C2 C5 C4 . 1.8(7)
C10 C2 C5 C1 . 179.6(4)
