#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/22/2222291.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_2222291
loop_
_publ_author_name
'Xiao, Zi-Dan'
'Pan, Tong'
'Yang, Dao-Wu'
_publ_section_title
;
 3-Bromo-9-(4-chlorobenzyl)-9H-carbazole
;
_journal_coeditor_code           DN2457
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1476
_journal_paper_doi               10.1107/S1600536809019448
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H13 Br Cl N'
_chemical_formula_moiety         'C19 H13 Br Cl N'
_chemical_formula_sum            'C19 H13 Br Cl N'
_chemical_formula_weight         370.66
_chemical_melting_point          432
_chemical_name_systematic
;
3-Bromo-9-(4-chlorobenzyl)-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                   17.272(4)
_cell_length_b                   15.789(3)
_cell_length_c                   5.5948(11)
_cell_measurement_reflns_used    5012
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.892
_cell_measurement_theta_min      1.747
_cell_volume                     1525.7(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10796
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.864
_exptl_absorpt_correction_T_max  0.8033
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.465
_refine_ls_abs_structure_details 'Flack (1983), 1163 Friedel pairs'
_refine_ls_abs_structure_Flack   0.014(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0232
_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)+(0.0295P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                2401
_reflns_number_total             2664
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2457.cif
_cod_data_source_block           I
_cod_database_code               2222291
_cod_database_fobs_code          2222291
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 0.258680(12) 0.185476(15) 1.32912(10) 0.02288(9) Uani d . 1 . .
Cl Cl1 0.65120(4) 0.59416(4) 0.8259(2) 0.02847(16) Uani d . 1 . .
N N1 0.53701(13) 0.18736(14) 0.6844(4) 0.0167(5) Uani d . 1 . .
C C1 0.58534(13) 0.13162(15) 0.8041(6) 0.0152(6) Uani d . 1 . .
C C2 0.66094(15) 0.10636(17) 0.7491(5) 0.0209(7) Uani d . 1 . .
H H2 0.6862 0.1270 0.6143 0.025 Uiso calc R 1 . .
C C3 0.69681(15) 0.04979(18) 0.9013(5) 0.0224(7) Uani d . 1 . .
H H3 0.7471 0.0322 0.8682 0.027 Uiso calc R 1 . .
C C4 0.65932(16) 0.01831(19) 1.1042(6) 0.0233(7) Uani d . 1 . .
H H4 0.6848 -0.0198 1.2038 0.028 Uiso calc R 1 . .
C C5 0.58446(15) 0.04349(18) 1.1579(5) 0.0186(7) Uani d . 1 . .
H H5 0.5597 0.0227 1.2934 0.022 Uiso calc R 1 . .
C C6 0.54667(15) 0.10001(16) 1.0080(5) 0.0167(6) Uani d . 1 . .
C C7 0.47140(14) 0.13996(16) 1.0130(5) 0.0135(6) Uani d . 1 . .
C C8 0.40812(14) 0.13595(18) 1.1675(5) 0.0160(6) Uani d . 1 . .
H H8 0.4082 0.1001 1.2993 0.019 Uiso calc R 1 . .
C C9 0.34553(15) 0.18694(17) 1.1181(5) 0.0174(6) Uani d . 1 . .
C C10 0.34293(15) 0.24129(18) 0.9223(5) 0.0210(7) Uani d . 1 . .
H H10 0.2993 0.2746 0.8960 0.025 Uiso calc R 1 . .
C C11 0.40475(15) 0.24581(18) 0.7676(5) 0.0202(7) Uani d . 1 . .
H H11 0.4040 0.2824 0.6373 0.024 Uiso calc R 1 . .
C C12 0.46844(13) 0.19405(14) 0.8117(6) 0.0147(5) Uani d . 1 . .
C C13 0.55872(15) 0.24502(16) 0.4941(5) 0.0193(7) Uani d . 1 . .
H H13A 0.5160 0.2495 0.3822 0.023 Uiso calc R 1 . .
H H13B 0.6026 0.2214 0.4087 0.023 Uiso calc R 1 . .
C C14 0.57980(15) 0.33317(17) 0.5812(5) 0.0151(6) Uani d . 1 . .
C C15 0.62228(15) 0.34401(18) 0.7921(6) 0.0227(7) Uani d . 1 . .
H H15 0.6358 0.2971 0.8835 0.027 Uiso calc R 1 . .
C C16 0.64432(14) 0.42472(17) 0.8658(6) 0.0215(7) Uani d . 1 . .
H H16 0.6729 0.4319 1.0052 0.026 Uiso calc R 1 . .
C C17 0.62343(16) 0.49356(17) 0.7311(5) 0.0187(6) Uani d . 1 . .
C C18 0.58085(15) 0.48457(18) 0.5212(6) 0.0223(7) Uani d . 1 . .
H H18 0.5671 0.5318 0.4313 0.027 Uiso calc R 1 . .
C C19 0.55924(15) 0.40353(17) 0.4486(5) 0.0192(7) Uani d . 1 . .
H H19 0.5306 0.3967 0.3091 0.023 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'
Cl Cl 0.1484 0.1585 '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 C12 . . 108.4(2) ?
C1 N1 C13 . . 126.7(2) ?
C12 N1 C13 . . 123.4(2) ?
N1 C1 C2 . . 129.6(3) ?
N1 C1 C6 . . 109.2(2) ?
C2 C1 C6 . . 121.2(3) ?
C3 C2 C1 . . 117.9(3) ?
C3 C2 H2 . . 121.1 ?
C1 C2 H2 . . 121.1 ?
C2 C3 C4 . . 121.5(3) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 119.5(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.5(2) ?
C5 C6 C7 . . 133.8(3) ?
C1 C6 C7 . . 106.7(2) ?
C8 C7 C12 . . 119.5(2) ?
C8 C7 C6 . . 134.2(3) ?
C12 C7 C6 . . 106.3(2) ?
C9 C8 C7 . . 117.7(3) ?
C9 C8 H8 . . 121.2 ?
C7 C8 H8 . . 121.2 ?
C8 C9 C10 . . 123.0(3) ?
C8 C9 Br1 . . 119.1(2) ?
C10 C9 Br1 . . 117.9(2) ?
C11 C10 C9 . . 120.1(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 118.1(3) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
N1 C12 C11 . . 129.0(3) ?
N1 C12 C7 . . 109.4(2) ?
C11 C12 C7 . . 121.6(3) ?
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 . . 120.2(3) ?
C15 C14 C13 . . 120.5(3) ?
C16 C15 C14 . . 120.3(3) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C17 C16 C15 . . 119.4(3) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C16 C17 C18 . . 121.4(3) ?
C16 C17 Cl1 . . 118.9(2) ?
C18 C17 Cl1 . . 119.7(2) ?
C17 C18 C19 . . 118.8(3) ?
C17 C18 H18 . . 120.6 ?
C19 C18 H18 . . 120.6 ?
C14 C19 C18 . . 120.8(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 C9 . 1.909(3) ?
Cl1 C17 . 1.742(3) ?
N1 C1 . 1.385(3) ?
N1 C12 . 1.386(3) ?
N1 C13 . 1.450(3) ?
C1 C2 . 1.399(3) ?
C1 C6 . 1.413(4) ?
C2 C3 . 1.381(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.398(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.445(3) ?
C7 C8 . 1.395(4) ?
C7 C12 . 1.415(4) ?
C8 C9 . 1.376(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.392(4) ?
C10 C11 . 1.376(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.393(4) ?
C11 H11 . 0.9300 ?
C13 C14 . 1.519(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.382(4) ?
C14 C15 . 1.400(4) ?
C15 C16 . 1.392(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.371(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.393(4) ?
C18 C19 . 1.393(4) ?
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 . . . . -12.0(4) ?
C12 N1 C1 C6 . . . . 1.6(3) ?
C13 N1 C1 C6 . . . . 167.8(2) ?
N1 C1 C2 C3 . . . . 179.4(3) ?
C6 C1 C2 C3 . . . . -0.4(4) ?
C1 C2 C3 C4 . . . . 0.1(4) ?
C2 C3 C4 C5 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
C4 C5 C6 C7 . . . . -178.3(3) ?
N1 C1 C6 C5 . . . . -179.2(2) ?
C2 C1 C6 C5 . . . . 0.6(4) ?
N1 C1 C6 C7 . . . . -0.9(3) ?
C2 C1 C6 C7 . . . . 178.9(2) ?
C5 C6 C7 C8 . . . . -1.2(5) ?
C1 C6 C7 C8 . . . . -179.1(3) ?
C5 C6 C7 C12 . . . . 177.8(3) ?
C1 C6 C7 C12 . . . . -0.1(3) ?
C12 C7 C8 C9 . . . . -1.3(4) ?
C6 C7 C8 C9 . . . . 177.6(3) ?
C7 C8 C9 C10 . . . . 0.2(4) ?
C7 C8 C9 Br1 . . . . -178.51(19) ?
C8 C9 C10 C11 . . . . 0.0(4) ?
Br1 C9 C10 C11 . . . . 178.8(2) ?
C9 C10 C11 C12 . . . . 0.8(4) ?
C1 N1 C12 C11 . . . . 176.2(3) ?
C13 N1 C12 C11 . . . . 9.5(4) ?
C1 N1 C12 C7 . . . . -1.7(3) ?
C13 N1 C12 C7 . . . . -168.4(2) ?
C10 C11 C12 N1 . . . . -179.6(3) ?
C10 C11 C12 C7 . . . . -1.9(4) ?
C8 C7 C12 N1 . . . . -179.7(2) ?
C6 C7 C12 N1 . . . . 1.2(3) ?
C8 C7 C12 C11 . . . . 2.2(4) ?
C6 C7 C12 C11 . . . . -177.0(2) ?
C1 N1 C13 C14 . . . . -93.3(3) ?
C12 N1 C13 C14 . . . . 70.8(3) ?
N1 C13 C14 C19 . . . . -142.8(3) ?
N1 C13 C14 C15 . . . . 39.3(4) ?
C19 C14 C15 C16 . . . . -0.7(4) ?
C13 C14 C15 C16 . . . . 177.2(2) ?
C14 C15 C16 C17 . . . . 0.6(4) ?
C15 C16 C17 C18 . . . . -0.3(4) ?
C15 C16 C17 Cl1 . . . . 179.8(2) ?
C16 C17 C18 C19 . . . . 0.1(4) ?
Cl1 C17 C18 C19 . . . . 180.0(2) ?
C15 C14 C19 C18 . . . . 0.6(4) ?
C13 C14 C19 C18 . . . . -177.4(2) ?
C17 C18 C19 C14 . . . . -0.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742459
