#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/28/2102830.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_2102830
loop_
_publ_author_name
'Ojala, William H.'
'Smieja, Jonathan M.'
'Spude, Jill M.'
'Arola, Trina M.'
'Kuspa, Marika K.'
'Herrera, Nell'
'Ojala, Charles R.'
_publ_section_title
;
 Isostructuralism among `bridge-flipped' isomeric benzylideneanilines
 and phenylhydrazones
;
_journal_coeditor_code           GP5015
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              485
_journal_page_last               496
_journal_paper_doi               10.1107/S0108768107018034
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C14 H12 Br N'
_chemical_formula_sum            'C14 H12 Br N'
_chemical_formula_weight         274.16
_chemical_melting_point          .79E-80
_chemical_name_systematic
;
 N-(2-methylbenzylidene)-2-bromoaniline
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.3550(12)
_cell_length_b                   11.6667(11)
_cell_length_c                   14.9529(14)
_cell_measurement_reflns_used    3828
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.004
_cell_measurement_theta_min      2.318
_cell_volume                     2329.8(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21202
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    3.498
_exptl_absorpt_correction_T_max  0.589
_exptl_absorpt_correction_T_min  0.293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0292
_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)+(0.0269P)²+2.7709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0673
_reflns_number_gt                1865
_reflns_number_total             2059
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gp5015.cif
_cod_data_source_block           VI
_cod_database_code               2102830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
Br Br1 0.403961(19) 0.13753(2) 0.436421(19) 0.03074(11) Uani d . 1
C C1 0.22137(18) 0.2653(2) 0.43832(15) 0.0205(5) Uani d . 1
C C2 0.26762(18) 0.1651(2) 0.40779(16) 0.0204(5) Uani d . 1
C C3 0.2174(2) 0.0840(2) 0.35753(16) 0.0248(6) Uani d . 1
H H3 0.2505 0.0160 0.3388 0.030 Uiso calc R 1
C C4 0.1181(2) 0.1031(2) 0.33470(18) 0.0280(6) Uani d . 1
H H4 0.0829 0.0482 0.2997 0.034 Uiso calc R 1
C C5 0.0702(2) 0.2017(2) 0.36277(18) 0.0286(6) Uani d . 1
H H5 0.0022 0.2145 0.3472 0.034 Uiso calc R 1
C C6 0.12122(19) 0.2820(2) 0.41361(17) 0.0242(6) Uani d . 1
H H6 0.0876 0.3498 0.4321 0.029 Uiso calc R 1
C C7 0.28321(18) 0.4964(2) 0.59680(16) 0.0196(5) Uani d . 1
C C8 0.23004(19) 0.5637(2) 0.65885(15) 0.0216(5) Uani d . 1
C C9 0.2798(2) 0.6546(2) 0.69962(17) 0.0261(6) Uani d . 1
H H9 0.2447 0.7019 0.7408 0.031 Uiso calc R 1
C C10 0.3793(2) 0.6774(2) 0.68137(18) 0.0292(6) Uani d . 1
H H10 0.4119 0.7394 0.7105 0.035 Uiso calc R 1
C C11 0.4320(2) 0.6107(2) 0.62096(18) 0.0272(6) Uani d . 1
H H11 0.5004 0.6264 0.6086 0.033 Uiso calc R 1
C C12 0.38379(18) 0.5211(2) 0.57910(16) 0.0234(6) Uani d . 1
H H12 0.4195 0.4753 0.5374 0.028 Uiso calc R 1
C C13 0.23428(18) 0.4020(2) 0.54873(15) 0.0206(5) Uani d . 1
H H13 0.1682 0.3807 0.5654 0.025 Uiso calc R 1
C C14 0.11913(18) 0.5398(2) 0.68217(17) 0.0246(6) Uani d . 1
H H14A 0.0959 0.5960 0.7263 0.037 Uiso calc R 1
H H14B 0.1129 0.4624 0.7071 0.037 Uiso calc R 1
H H14C 0.0783 0.5457 0.6279 0.037 Uiso calc R 1
N N1 0.27694(15) 0.34772(17) 0.48573(13) 0.0217(5) Uani d . 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
_geom_angle_publ_flag
C2 C1 C6 116.9(2) n
C2 C1 N1 120.2(2) n
C6 C1 N1 122.8(2) n
C3 C2 C1 122.4(2) n
C3 C2 Br1 118.14(19) n
C1 C2 Br1 119.48(18) n
C2 C3 C4 119.2(2) n
C2 C3 H3 120 n
C4 C3 H3 120 n
C5 C4 C3 120.1(2) n
C5 C4 H4 120 n
C3 C4 H4 120 n
C4 C5 C6 120.1(2) n
C4 C5 H5 120 n
C6 C5 H5 120 n
C5 C6 C1 121.3(2) n
C5 C6 H6 119 n
C1 C6 H6 119 n
C12 C7 C8 119.6(2) n
C12 C7 C13 119.3(2) n
C8 C7 C13 121.1(2) n
C9 C8 C7 118.2(2) n
C9 C8 C14 119.7(2) n
C7 C8 C14 122.1(2) n
C10 C9 C8 121.3(2) n
C10 C9 H9 119 n
C8 C9 H9 119 n
C9 C10 C11 120.6(2) n
C9 C10 H10 120 n
C11 C10 H10 120 n
C12 C11 C10 119.0(2) n
C12 C11 H11 121 n
C10 C11 H11 121 n
C11 C12 C7 121.3(2) n
C11 C12 H12 119 n
C7 C12 H12 119 n
N1 C13 C7 122.5(2) y
N1 C13 H13 119 n
C7 C13 H13 119 n
C8 C14 H14A 110 n
C8 C14 H14B 110 n
H14A C14 H14B 110 n
C8 C14 H14C 110 n
H14A C14 H14C 110 n
H14B C14 H14C 110 n
C13 N1 C1 118.6(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 1.898(2) y
C1 C2 1.398(3) n
C1 C6 1.401(3) n
C1 N1 1.407(3) y
C2 C3 1.383(4) n
C3 C4 1.388(4) n
C3 H3 0.95 n
C4 C5 1.382(4) n
C4 H4 0.95 n
C5 C6 1.385(4) n
C5 H5 0.95 n
C6 H6 0.95 n
C7 C12 1.399(3) n
C7 C8 1.408(3) n
C7 C13 1.469(3) y
C8 C9 1.392(4) n
C8 C14 1.547(3) y
C9 C10 1.383(4) n
C9 H9 0.95 n
C10 C11 1.385(4) n
C10 H10 0.95 n
C11 C12 1.377(4) n
C11 H11 0.95 n
C12 H12 0.95 n
C13 N1 1.270(3) y
C13 H13 0.95 n
C14 H14A 0.98 n
C14 H14B 0.98 n
C14 H14C 0.98 n
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.7(3) n
N1 C1 C2 C3 -177.1(2) n
C6 C1 C2 Br1 178.79(18) n
N1 C1 C2 Br1 3.4(3) n
C1 C2 C3 C4 1.4(4) n
Br1 C2 C3 C4 -179.09(19) n
C2 C3 C4 C5 -0.6(4) n
C3 C4 C5 C6 0.1(4) n
C4 C5 C6 C1 -0.5(4) n
C2 C1 C6 C5 1.2(4) n
N1 C1 C6 C5 176.5(2) n
C12 C7 C8 C9 1.0(3) n
C13 C7 C8 C9 -177.6(2) n
C12 C7 C8 C14 -179.2(2) n
C13 C7 C8 C14 2.1(3) n
C7 C8 C9 C10 -1.2(4) n
C14 C8 C9 C10 179.0(2) n
C8 C9 C10 C11 0.7(4) n
C9 C10 C11 C12 0.1(4) n
C10 C11 C12 C7 -0.3(4) n
C8 C7 C12 C11 -0.3(4) n
C13 C7 C12 C11 178.4(2) n
C12 C7 C13 N1 -6.3(4) y
C8 C7 C13 N1 172.3(2) n
C7 C13 N1 C1 -174.6(2) y
C2 C1 N1 C13 -144.3(2) n
C6 C1 N1 C13 40.6(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654485
