#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222306.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_2222306
loop_
_publ_author_name
'Wang, Cheng-Feng'
_publ_section_title
;
 3-Bromo-9-(4-fluorobenzyl)-9H-carbazole
;
_journal_coeditor_code           GK2211
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1589
_journal_paper_doi               10.1107/S160053680901976X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H13 Br F N'
_chemical_formula_moiety         'C19 H13 Br F N'
_chemical_formula_sum            'C19 H13 Br F N'
_chemical_formula_weight         354.21
_chemical_melting_point_gt       420
_chemical_melting_point_lt       422
_chemical_name_systematic
;
3-Bromo-9-(4-fluorobenzyl)-9H-carbazole
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   17.407(4)
_cell_length_b                   15.068(3)
_cell_length_c                   5.5865(11)
_cell_measurement_reflns_used    4959
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.79
_cell_volume                     1465.3(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  'confocal multilayer X-ray optic'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9581
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.811
_exptl_absorpt_correction_T_max  0.8064
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.690
_refine_ls_abs_structure_details 'Flack (1983), 1139 Friedel pairs'
_refine_ls_abs_structure_Flack   0.004(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0325P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                2294
_reflns_number_total             2577
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2211.cif
_cod_data_source_block           I
_cod_database_code               2222306
_cod_database_fobs_code          2222306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_disorder_assembly
_atom_site_disorder_group
Br Br1 0.257719(15) 0.68839(2) 1.21455(15) 0.02390(12) Uani d . 1 . .
F F1 0.64152(11) 1.09557(12) 0.7028(5) 0.0424(5) Uani d . 1 . .
N N1 0.53809(16) 0.69284(17) 0.5849(5) 0.0157(7) Uani d . 1 . .
C C1 0.58579(15) 0.63539(19) 0.7103(7) 0.0154(6) Uani d . 1 . .
C C2 0.66123(18) 0.6094(2) 0.6612(6) 0.0195(8) Uani d . 1 . .
H H2 0.6871 0.6304 0.5270 0.023 Uiso calc R 1 . .
C C3 0.69613(18) 0.5514(2) 0.8188(6) 0.0224(9) Uani d . 1 . .
H H3 0.7461 0.5328 0.7882 0.027 Uiso calc R 1 . .
C C4 0.6585(2) 0.5198(2) 1.0230(7) 0.0240(9) Uani d . 1 . .
H H4 0.6837 0.4815 1.1273 0.029 Uiso calc R 1 . .
C C5 0.58356(18) 0.5459(2) 1.0697(6) 0.0187(8) Uani d . 1 . .
H H5 0.5582 0.5247 1.2046 0.022 Uiso calc R 1 . .
C C6 0.54659(18) 0.6037(2) 0.9140(6) 0.0156(8) Uani d . 1 . .
C C7 0.47175(18) 0.6440(2) 0.9118(6) 0.0137(7) Uani d . 1 . .
C C8 0.40789(17) 0.6400(2) 1.0641(5) 0.0163(8) Uani d . 1 . .
H H8 0.4078 0.6034 1.1982 0.020 Uiso calc R 1 . .
C C9 0.34574(19) 0.6916(2) 1.0091(6) 0.0165(8) Uani d . 1 . .
C C10 0.34296(18) 0.7470(2) 0.8090(6) 0.0183(8) Uani d . 1 . .
H H10 0.2991 0.7804 0.7778 0.022 Uiso calc R 1 . .
C C11 0.40517(18) 0.7520(2) 0.6580(6) 0.0199(8) Uani d . 1 . .
H H11 0.4044 0.7896 0.5260 0.024 Uiso calc R 1 . .
C C12 0.46916(15) 0.70008(18) 0.7062(8) 0.0144(6) Uani d . 1 . .
C C13 0.56110(19) 0.7523(2) 0.3949(6) 0.0188(8) Uani d . 1 . .
H H13A 0.5193 0.7572 0.2808 0.023 Uiso calc R 1 . .
H H13B 0.6047 0.7268 0.3119 0.023 Uiso calc R 1 . .
C C14 0.58251(18) 0.8443(2) 0.4797(6) 0.0136(7) Uani d . 1 . .
C C15 0.62396(17) 0.8572(2) 0.6911(8) 0.0210(7) Uani d . 1 . .
H H15 0.6382 0.8084 0.7833 0.025 Uiso calc R 1 . .
C C16 0.64408(18) 0.9420(2) 0.7646(6) 0.0253(10) Uani d . 1 . .
H H16 0.6720 0.9504 0.9047 0.030 Uiso calc R 1 . .
C C17 0.6225(2) 1.0122(2) 0.6294(6) 0.0258(9) Uani d . 1 . .
C C18 0.5814(2) 1.0036(2) 0.4166(7) 0.0280(9) Uani d . 1 . .
H H18 0.5677 1.0528 0.3257 0.034 Uiso calc R 1 . .
C C19 0.56160(18) 0.9178(2) 0.3464(6) 0.0211(8) Uani d . 1 . .
H H19 0.5336 0.9097 0.2062 0.025 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'
F F 0.0171 0.0103 '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
C12 N1 C1 . . 108.7(3) ?
C12 N1 C13 . . 123.5(3) ?
C1 N1 C13 . . 126.2(3) ?
N1 C1 C2 . . 129.6(3) ?
N1 C1 C6 . . 109.2(3) ?
C2 C1 C6 . . 121.2(3) ?
C3 C2 C1 . . 117.8(3) ?
C3 C2 H2 . . 121.1 ?
C1 C2 H2 . . 121.1 ?
C2 C3 C4 . . 121.9(3) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 119.8(3) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 119.7(3) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 C1 . . 119.6(3) ?
C5 C6 C7 . . 133.6(3) ?
C1 C6 C7 . . 106.8(3) ?
C8 C7 C12 . . 119.3(3) ?
C8 C7 C6 . . 134.1(3) ?
C12 C7 C6 . . 106.6(3) ?
C9 C8 C7 . . 117.8(3) ?
C9 C8 H8 . . 121.1 ?
C7 C8 H8 . . 121.1 ?
C8 C9 C10 . . 123.2(3) ?
C8 C9 Br1 . . 118.9(3) ?
C10 C9 Br1 . . 117.9(3) ?
C11 C10 C9 . . 119.8(3) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 118.9(3) ?
C10 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
N1 C12 C11 . . 130.3(3) ?
N1 C12 C7 . . 108.7(2) ?
C11 C12 C7 . . 121.0(3) ?
N1 C13 C14 . . 114.0(3) ?
N1 C13 H13A . . 108.8 ?
C14 C13 H13A . . 108.8 ?
N1 C13 H13B . . 108.8 ?
C14 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.6 ?
C19 C14 C15 . . 118.7(3) ?
C19 C14 C13 . . 120.0(3) ?
C15 C14 C13 . . 121.3(3) ?
C16 C15 C14 . . 120.5(3) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C17 C16 C15 . . 119.0(3) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C16 C17 F1 . . 119.0(4) ?
C16 C17 C18 . . 123.1(3) ?
F1 C17 C18 . . 117.8(4) ?
C17 C18 C19 . . 116.9(3) ?
C17 C18 H18 . . 121.5 ?
C19 C18 H18 . . 121.5 ?
C14 C19 C18 . . 121.7(3) ?
C14 C19 H19 . . 119.1 ?
C18 C19 H19 . . 119.1 ?
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 C9 . 1.915(3) ?
F1 C17 . 1.363(4) ?
N1 C12 . 1.382(4) ?
N1 C1 . 1.389(4) ?
N1 C13 . 1.446(4) ?
C1 C2 . 1.398(4) ?
C1 C6 . 1.410(5) ?
C2 C3 . 1.381(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.399(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.437(4) ?
C7 C8 . 1.401(4) ?
C7 C12 . 1.427(5) ?
C8 C9 . 1.368(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.396(5) ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(4) ?
C11 H11 . 0.9300 ?
C13 C14 . 1.512(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.383(4) ?
C14 C15 . 1.397(5) ?
C15 C16 . 1.387(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.353(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.394(6) ?
C18 C19 . 1.394(5) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N1 C1 C2 . . . . -178.2(3) ?
C13 N1 C1 C2 . . . . -12.3(5) ?
C12 N1 C1 C6 . . . . 1.0(3) ?
C13 N1 C1 C6 . . . . 166.9(3) ?
N1 C1 C2 C3 . . . . 179.3(3) ?
C6 C1 C2 C3 . . . . 0.1(5) ?
C1 C2 C3 C4 . . . . -0.7(5) ?
C2 C3 C4 C5 . . . . 0.9(5) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
C4 C5 C6 C1 . . . . -0.1(5) ?
C4 C5 C6 C7 . . . . -178.7(3) ?
N1 C1 C6 C5 . . . . -179.0(3) ?
C2 C1 C6 C5 . . . . 0.3(5) ?
N1 C1 C6 C7 . . . . -0.1(4) ?
C2 C1 C6 C7 . . . . 179.2(3) ?
C5 C6 C7 C8 . . . . -0.4(7) ?
C1 C6 C7 C8 . . . . -179.1(4) ?
C5 C6 C7 C12 . . . . 177.9(4) ?
C1 C6 C7 C12 . . . . -0.8(4) ?
C12 C7 C8 C9 . . . . -0.8(5) ?
C6 C7 C8 C9 . . . . 177.3(3) ?
C7 C8 C9 C10 . . . . 0.5(5) ?
C7 C8 C9 Br1 . . . . -179.6(2) ?
C8 C9 C10 C11 . . . . -0.8(5) ?
Br1 C9 C10 C11 . . . . 179.4(2) ?
C9 C10 C11 C12 . . . . 1.3(5) ?
C1 N1 C12 C11 . . . . 176.9(3) ?
C13 N1 C12 C11 . . . . 10.5(5) ?
C1 N1 C12 C7 . . . . -1.6(3) ?
C13 N1 C12 C7 . . . . -167.9(3) ?
C10 C11 C12 N1 . . . . -179.9(3) ?
C10 C11 C12 C7 . . . . -1.7(5) ?
C8 C7 C12 N1 . . . . -180.0(3) ?
C6 C7 C12 N1 . . . . 1.5(4) ?
C8 C7 C12 C11 . . . . 1.4(5) ?
C6 C7 C12 C11 . . . . -177.1(3) ?
C12 N1 C13 C14 . . . . 72.0(4) ?
C1 N1 C13 C14 . . . . -92.0(4) ?
N1 C13 C14 C19 . . . . -141.1(3) ?
N1 C13 C14 C15 . . . . 39.5(4) ?
C19 C14 C15 C16 . . . . -0.4(5) ?
C13 C14 C15 C16 . . . . 179.1(3) ?
C14 C15 C16 C17 . . . . 0.5(5) ?
C15 C16 C17 F1 . . . . 179.3(3) ?
C15 C16 C17 C18 . . . . -0.7(5) ?
C16 C17 C18 C19 . . . . 0.8(5) ?
F1 C17 C18 C19 . . . . -179.2(3) ?
C15 C14 C19 C18 . . . . 0.5(5) ?
C13 C14 C19 C18 . . . . -178.9(3) ?
C17 C18 C19 C14 . . . . -0.7(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742475
