#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222705.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_2222705
loop_
_publ_author_name
'Huang, Peng-Mian'
'Wang, Xiao-Chun'
_publ_section_title
;
 9-Benzyl-3-bromo-9H-carbazole
;
_journal_coeditor_code           HB5016
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1763
_journal_paper_doi               10.1107/S1600536809024969
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H14 Br N'
_chemical_formula_moiety         'C19 H14 Br N'
_chemical_formula_sum            'C19 H14 Br N'
_chemical_formula_weight         336.22
_chemical_melting_point_gt       392
_chemical_melting_point_lt       394
_chemical_name_systematic
;
9-Benzyl-3-bromo-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                   17.629(3)
_cell_length_b                   14.666(2)
_cell_length_c                   5.6420(8)
_cell_measurement_reflns_used    3798
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.8
_cell_volume                     1458.7(4)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     0.71070
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14426
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.519
_refine_ls_abs_structure_details 'Flack (1983), 1521 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.005(10)
_refine_ls_extinction_coef       0.0148(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0359
_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)+(0.0241P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                2801
_reflns_number_total             3441
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5016.cif
_cod_data_source_block           I
_cod_database_code               2222705
_cod_database_fobs_code          2222705
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'-x, -y, 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 0.257493(13) 0.192950(18) 0.66598(14) 0.02943(11) Uani d . 1 . .
N N1 0.53686(13) 0.19508(14) 0.0539(4) 0.0196(5) Uani d . 1 . .
C C1 0.46874(12) 0.20289(15) 0.1699(6) 0.0180(5) Uani d . 1 . .
C C2 0.40547(16) 0.25415(17) 0.1164(5) 0.0229(7) Uani d . 1 . .
H H2 0.4049 0.2918 -0.0206 0.027 Uiso calc R 1 . .
C C3 0.34289(16) 0.25037(19) 0.2638(5) 0.0231(7) Uani d . 1 . .
H H3 0.2988 0.2849 0.2278 0.028 Uiso calc R 1 . .
C C4 0.34503(16) 0.19535(18) 0.4663(5) 0.0206(7) Uani d . 1 . .
C C5 0.40726(15) 0.14351(19) 0.5264(5) 0.0191(6) Uani d . 1 . .
H H5 0.4072 0.1064 0.6643 0.023 Uiso calc R 1 . .
C C6 0.47028(15) 0.14744(17) 0.3781(5) 0.0176(6) Uani d . 1 . .
C C7 0.58394(13) 0.13641(16) 0.1792(6) 0.0191(6) Uani d . 1 . .
C C8 0.65823(14) 0.10891(17) 0.1344(6) 0.0228(7) Uani d . 1 . .
H H8 0.6848 0.1303 -0.0013 0.027 Uiso calc R 1 . .
C C9 0.69198(16) 0.0502(2) 0.2913(5) 0.0269(7) Uani d . 1 . .
H H9 0.7424 0.0303 0.2617 0.032 Uiso calc R 1 . .
C C10 0.65424(18) 0.0186(2) 0.4947(5) 0.0260(7) Uani d . 1 . .
H H10 0.6794 -0.0215 0.6010 0.031 Uiso calc R 1 . .
C C11 0.58048(16) 0.04587(18) 0.5403(5) 0.0222(7) Uani d . 1 . .
H H11 0.5547 0.0246 0.6774 0.027 Uiso calc R 1 . .
C C12 0.54435(15) 0.10506(18) 0.3825(5) 0.0179(6) Uani d . 1 . .
C C13 0.56053(16) 0.25418(18) -0.1405(5) 0.0224(7) Uani d . 1 . .
H H13A 0.5185 0.2588 -0.2563 0.027 Uiso calc R 1 . .
H H13B 0.6042 0.2258 -0.2223 0.027 Uiso calc R 1 . .
C C14 0.58274(15) 0.34943(19) -0.0620(5) 0.0197(6) Uani d . 1 . .
C C15 0.62312(14) 0.36493(17) 0.1461(6) 0.0241(6) Uani d . 1 . .
H H15 0.6360 0.3154 0.2470 0.029 Uiso calc R 1 . .
C C16 0.64439(15) 0.4530(2) 0.2054(6) 0.0307(8) Uani d . 1 . .
H H16 0.6726 0.4631 0.3464 0.037 Uiso calc R 1 . .
C C17 0.6255(2) 0.5257(2) 0.0643(6) 0.0344(9) Uani d . 1 . .
H H17 0.6402 0.5858 0.1077 0.041 Uiso calc R 1 . .
C C18 0.58455(17) 0.5108(2) -0.1427(7) 0.0336(8) Uani d . 1 . .
H H18 0.5713 0.5605 -0.2424 0.040 Uiso calc R 1 . .
C C19 0.56306(16) 0.42221(19) -0.2030(6) 0.0261(7) Uani d . 1 . .
H H19 0.5345 0.4120 -0.3432 0.031 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
C1 N1 C7 . . 109.4(2) ?
C1 N1 C13 . . 124.0(2) ?
C7 N1 C13 . . 125.4(2) ?
N1 C1 C2 . . 130.5(3) ?
N1 C1 C6 . . 109.1(2) ?
C2 C1 C6 . . 120.4(3) ?
C1 C2 C3 . . 119.5(3) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
C2 C3 C4 . . 119.5(3) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C5 C4 C3 . . 122.8(3) ?
C5 C4 Br1 . . 119.2(2) ?
C3 C4 Br1 . . 118.1(2) ?
C4 C5 C6 . . 117.7(3) ?
C4 C5 H5 . . 121.2 ?
C6 C5 H5 . . 121.2 ?
C5 C6 C1 . . 120.2(2) ?
C5 C6 C12 . . 133.8(3) ?
C1 C6 C12 . . 106.0(2) ?
N1 C7 C8 . . 130.4(3) ?
N1 C7 C12 . . 108.6(2) ?
C8 C7 C12 . . 121.0(3) ?
C9 C8 C7 . . 118.2(3) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
C8 C9 C10 . . 121.9(3) ?
C8 C9 H9 . . 119.0 ?
C10 C9 H9 . . 119.0 ?
C11 C10 C9 . . 120.1(3) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C12 . . 119.3(3) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C11 C12 C7 . . 119.5(2) ?
C11 C12 C6 . . 133.6(3) ?
C7 C12 C6 . . 106.9(2) ?
N1 C13 C14 . . 113.7(2) ?
N1 C13 H13A . . 108.8 ?
C14 C13 H13A . . 108.8 ?
N1 C13 H13B . . 108.8 ?
C14 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
C19 C14 C15 . . 119.3(3) ?
C19 C14 C13 . . 118.7(3) ?
C15 C14 C13 . . 121.9(2) ?
C16 C15 C14 . . 119.6(3) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C17 C16 C15 . . 121.3(3) ?
C17 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C16 C17 C18 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C17 C18 C19 . . 119.5(3) ?
C17 C18 H18 . . 120.2 ?
C19 C18 H18 . . 120.2 ?
C14 C19 C18 . . 120.9(3) ?
C14 C19 H19 . . 119.6 ?
C18 C19 H19 . . 119.6 ?
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 C4 . 1.911(3) ?
N1 C1 . 1.373(3) ?
N1 C7 . 1.389(3) ?
N1 C13 . 1.459(3) ?
C1 C2 . 1.379(3) ?
C1 C6 . 1.429(4) ?
C2 C3 . 1.382(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.399(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.377(4) ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.9500 ?
C6 C12 . 1.446(3) ?
C7 C8 . 1.393(3) ?
C7 C12 . 1.419(4) ?
C8 C9 . 1.371(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.405(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.385(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.397(4) ?
C11 H11 . 0.9500 ?
C13 C14 . 1.517(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C19 . 1.376(4) ?
C14 C15 . 1.392(4) ?
C15 C16 . 1.385(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.373(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.390(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.395(4) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
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
C7 N1 C1 C2 . . . . 178.6(3) ?
C13 N1 C1 C2 . . . . 10.5(4) ?
C7 N1 C1 C6 . . . . -0.3(3) ?
C13 N1 C1 C6 . . . . -168.5(2) ?
N1 C1 C2 C3 . . . . -179.9(3) ?
C6 C1 C2 C3 . . . . -1.1(4) ?
C1 C2 C3 C4 . . . . 0.7(4) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C2 C3 C4 Br1 . . . . 179.5(2) ?
C3 C4 C5 C6 . . . . 0.5(4) ?
Br1 C4 C5 C6 . . . . -179.48(19) ?
C4 C5 C6 C1 . . . . -0.8(4) ?
C4 C5 C6 C12 . . . . 179.2(3) ?
N1 C1 C6 C5 . . . . -179.8(2) ?
C2 C1 C6 C5 . . . . 1.2(4) ?
N1 C1 C6 C12 . . . . 0.2(3) ?
C2 C1 C6 C12 . . . . -178.9(2) ?
C1 N1 C7 C8 . . . . -178.7(3) ?
C13 N1 C7 C8 . . . . -10.7(4) ?
C1 N1 C7 C12 . . . . 0.3(3) ?
C13 N1 C7 C12 . . . . 168.3(2) ?
N1 C7 C8 C9 . . . . 179.3(3) ?
C12 C7 C8 C9 . . . . 0.4(4) ?
C7 C8 C9 C10 . . . . -0.8(4) ?
C8 C9 C10 C11 . . . . 0.7(4) ?
C9 C10 C11 C12 . . . . -0.1(4) ?
C10 C11 C12 C7 . . . . -0.3(4) ?
C10 C11 C12 C6 . . . . -178.6(3) ?
N1 C7 C12 C11 . . . . -179.0(2) ?
C8 C7 C12 C11 . . . . 0.1(4) ?
N1 C7 C12 C6 . . . . -0.2(3) ?
C8 C7 C12 C6 . . . . 178.9(2) ?
C5 C6 C12 C11 . . . . -1.5(5) ?
C1 C6 C12 C11 . . . . 178.5(3) ?
C5 C6 C12 C7 . . . . 180.0(3) ?
C1 C6 C12 C7 . . . . 0.0(3) ?
C1 N1 C13 C14 . . . . 73.6(3) ?
C7 N1 C13 C14 . . . . -92.7(3) ?
N1 C13 C14 C19 . . . . -141.7(3) ?
N1 C13 C14 C15 . . . . 39.1(4) ?
C19 C14 C15 C16 . . . . -1.5(4) ?
C13 C14 C15 C16 . . . . 177.7(3) ?
C14 C15 C16 C17 . . . . 0.9(4) ?
C15 C16 C17 C18 . . . . -0.4(5) ?
C16 C17 C18 C19 . . . . 0.3(5) ?
C15 C14 C19 C18 . . . . 1.5(4) ?
C13 C14 C19 C18 . . . . -177.7(3) ?
C17 C18 C19 C14 . . . . -0.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3581720
