#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017706.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_2017706
loop_
_publ_author_name
'Quiroz-Guzman, Mauricio'
'Brown, Seth N.'
_publ_section_title
;
 Tris(4-bromophenyl)aminium hexachloridoantimonate (`Magic Blue'): a
 strong oxidant with low inner-sphere reorganization
;
_journal_coeditor_code           FN3059
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m171
_journal_page_last               m173
_journal_paper_doi               10.1107/S0108270110019748
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H12 Br3 N'
_chemical_formula_moiety         'C18 H12 Br3 N'
_chemical_formula_sum            'C18 H12 Br3 N'
_chemical_formula_weight         482.02
_chemical_melting_point_gt       141
_chemical_melting_point_lt       143
_chemical_name_common            Tris(4-bromophenyl)amine
_chemical_name_systematic
;
4-bromo-N,N-bis(4-bromophenyl)aniline
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.534(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3970(6)
_cell_length_b                   16.0352(15)
_cell_length_c                   11.3688(7)
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.777
_cell_measurement_theta_min      7.181
_cell_volume                     1633.5(2)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2007; Sheldrick, 2008b)
;
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008b)'
_computing_publication_material
;
XCIF (Sheldrick, 2008b) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker d8 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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13565
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    7.404
_exptl_absorpt_correction_T_max  0.5247
_exptl_absorpt_correction_T_min  0.3659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.574
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0304
_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)+(0.0233P)²+1.6729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                2692
_reflns_number_total             3379
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3059.cif
_cod_data_source_block           II
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2017706
_cod_database_fobs_code          2017706
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.11627(4) 0.00634(2) 0.11657(3) 0.02229(10) Uani d . 1 . .
Br Br3 0.43055(4) 0.11736(3) 1.02807(3) 0.02652(11) Uani d . 1 . .
Br Br2 0.99074(4) 0.26014(3) 0.37581(3) 0.02854(11) Uani d . 1 . .
N N1 0.4493(3) 0.12544(19) 0.4997(2) 0.0154(6) Uani d . 1 . .
C C11 0.3189(3) 0.0978(2) 0.4082(3) 0.0149(7) Uani d . 1 . .
C C12 0.2277(4) 0.0385(2) 0.4383(3) 0.0159(7) Uani d . 1 . .
H H12 0.2547 0.0162 0.5195 0.019 Uiso calc R 1 . .
C C13 0.0981(4) 0.0115(2) 0.3518(3) 0.0181(8) Uani d . 1 . .
H H13 0.0351 -0.0281 0.3735 0.022 Uiso calc R 1 . .
C C14 0.0620(3) 0.0432(2) 0.2332(3) 0.0160(7) Uani d . 1 . .
C C15 0.1517(3) 0.1012(2) 0.2009(3) 0.0144(7) Uani d . 1 . .
H H15 0.1263 0.1219 0.1189 0.017 Uiso calc R 1 . .
C C16 0.2786(3) 0.1288(2) 0.2887(3) 0.0141(7) Uani d . 1 . .
H H16 0.3396 0.1697 0.2671 0.017 Uiso calc R 1 . .
C C31 0.4482(4) 0.1271(2) 0.6243(3) 0.0150(7) Uani d . 1 . .
C C32 0.5689(4) 0.0950(2) 0.7179(3) 0.0162(7) Uani d . 1 . .
H H32 0.6537 0.0739 0.6986 0.019 Uiso calc R 1 . .
C C33 0.5649(4) 0.0939(2) 0.8377(3) 0.0190(8) Uani d . 1 . .
H H33 0.6475 0.0730 0.9016 0.023 Uiso calc R 1 . .
C C34 0.4403(4) 0.1232(2) 0.8644(3) 0.0180(8) Uani d . 1 . .
C C35 0.3207(4) 0.1560(2) 0.7737(3) 0.0197(8) Uani d . 1 . .
H H35 0.2357 0.1764 0.7934 0.024 Uiso calc R 1 . .
C C36 0.3266(4) 0.1586(2) 0.6540(3) 0.0181(8) Uani d . 1 . .
H H36 0.2461 0.1825 0.5912 0.022 Uiso calc R 1 . .
C C21 0.5765(3) 0.1551(2) 0.4704(3) 0.0142(7) Uani d . 1 . .
C C22 0.6151(4) 0.1242(2) 0.3699(3) 0.0160(7) Uani d . 1 . .
H H22 0.5561 0.0818 0.3201 0.019 Uiso calc R 1 . .
C C23 0.7386(3) 0.1548(2) 0.3417(3) 0.0158(7) Uani d . 1 . .
H H23 0.7637 0.1342 0.2722 0.019 Uiso calc R 1 . .
C C24 0.8245(3) 0.2152(2) 0.4156(3) 0.0169(8) Uani d . 1 . .
C C25 0.7925(4) 0.2451(2) 0.5188(3) 0.0168(7) Uani d . 1 . .
H H25 0.8546 0.2857 0.5705 0.020 Uiso calc R 1 . .
C C26 0.6684(4) 0.2146(2) 0.5450(3) 0.0162(7) Uani d . 1 . .
H H26 0.6450 0.2347 0.6156 0.019 Uiso calc R 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
_geom_angle_publ_flag
C21 N1 C11 . . 122.4(3) ?
C21 N1 C31 . . 119.3(3) ?
C11 N1 C31 . . 118.2(3) ?
C16 C11 C12 . . 118.7(3) ?
C16 C11 N1 . . 121.8(3) ?
C12 C11 N1 . . 119.6(3) ?
C13 C12 C11 . . 121.0(3) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C14 C13 C12 . . 118.8(3) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C15 C14 C13 . . 121.2(3) ?
C15 C14 Br1 . . 120.5(2) ?
C13 C14 Br1 . . 118.3(3) ?
C16 C15 C14 . . 119.3(3) ?
C16 C15 H15 . . 120.3 ?
C14 C15 H15 . . 120.3 ?
C15 C16 C11 . . 121.0(3) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
C36 C31 C32 . . 119.3(3) ?
C36 C31 N1 . . 120.4(3) ?
C32 C31 N1 . . 120.3(3) ?
C33 C32 C31 . . 120.1(3) ?
C33 C32 H32 . . 120.0 ?
C31 C32 H32 . . 120.0 ?
C32 C33 C34 . . 119.5(3) ?
C32 C33 H33 . . 120.2 ?
C34 C33 H33 . . 120.2 ?
C33 C34 C35 . . 121.4(3) ?
C33 C34 Br3 . . 119.7(2) ?
C35 C34 Br3 . . 118.9(2) ?
C36 C35 C34 . . 118.9(3) ?
C36 C35 H35 . . 120.6 ?
C34 C35 H35 . . 120.6 ?
C35 C36 C31 . . 120.8(3) ?
C35 C36 H36 . . 119.6 ?
C31 C36 H36 . . 119.6 ?
C22 C21 C26 . . 118.5(3) ?
C22 C21 N1 . . 121.5(3) ?
C26 C21 N1 . . 120.0(3) ?
C23 C22 C21 . . 120.7(3) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C24 C23 C22 . . 119.2(3) ?
C24 C23 H23 . . 120.4 ?
C22 C23 H23 . . 120.4 ?
C23 C24 C25 . . 121.7(3) ?
C23 C24 Br2 . . 119.8(2) ?
C25 C24 Br2 . . 118.5(3) ?
C26 C25 C24 . . 118.4(3) ?
C26 C25 H25 . . 120.8 ?
C24 C25 H25 . . 120.8 ?
C25 C26 C21 . . 121.5(3) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C14 . 1.891(3) ?
Br3 C34 . 1.893(3) ?
Br2 C24 . 1.895(3) ?
N1 C21 . 1.416(4) ?
N1 C11 . 1.419(4) ?
N1 C31 . 1.420(4) ?
C11 C16 . 1.388(4) ?
C11 C12 . 1.390(5) ?
C12 C13 . 1.384(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.378(5) ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C31 C36 . 1.381(4) ?
C31 C32 . 1.399(4) ?
C32 C33 . 1.373(4) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.378(5) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.380(5) ?
C35 C36 . 1.379(4) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C21 C22 . 1.390(4) ?
C21 C26 . 1.391(5) ?
C22 C23 . 1.383(4) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.374(5) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.382(5) ?
C25 C26 . 1.377(5) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 226401
