#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/84/2208458.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_2208458
loop_
_publ_author_name
'Duan, Xue-Min'
'Huang, Peng-Mian'
'Li, Jiang-Sheng'
'Zheng, Peng-Wu'
_publ_section_title
;
 (3,6-Dibromo-9H-carbazol-9-yl)(phenyl)methanone
;
_journal_coeditor_code           XU2001
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o995
_journal_page_last               o996
_journal_paper_doi               10.1107/S1600536806004144
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H11 Br2 N O'
_chemical_formula_moiety         'C19 H11 Br2 N O'
_chemical_formula_sum            'C19 H11 Br2 N O'
_chemical_formula_weight         429.11
_chemical_melting_point          .483E-305
_chemical_name_systematic
;
(3,6-Dibromo-9H-carbazol-9-yl)(phenyl)methanone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                61.384(4)
_cell_angle_beta                 80.036(5)
_cell_angle_gamma                72.641(5)
_cell_formula_units_Z            2
_cell_length_a                   7.398(2)
_cell_length_b                   11.223(3)
_cell_length_c                   11.431(4)
_cell_measurement_reflns_used    1944
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.9
_cell_volume                     794.7(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART 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  0.034
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4061
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.103
_exptl_absorpt_correction_T_max  0.362
_exptl_absorpt_correction_T_min  0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.63
_refine_ls_extinction_coef       0.081(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.042
_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)+(0.0624P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.116
_reflns_number_gt                2170
_reflns_number_total             2780
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2001.cif
_cod_data_source_block           I
_cod_database_code               2208458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.25133(7) 1.00740(5) 0.91158(5) 0.0593(2) Uani d . 1
Br Br2 0.30606(7) 0.13097(5) 1.38699(5) 0.0662(2) Uani d . 1
O O1 0.1005(5) 0.4341(3) 0.7158(3) 0.0614(9) Uani d . 1
N N1 0.2153(4) 0.5385(3) 0.8036(3) 0.0358(7) Uani d . 1
C C1 0.2197(5) 0.6618(4) 0.8077(4) 0.0340(8) Uani d . 1
C C2 0.1881(6) 0.8001(4) 0.7088(4) 0.0399(9) Uani d . 1
H H2 0.1633 0.8238 0.6222 0.048 Uiso calc R 1
C C3 0.1947(6) 0.9003(4) 0.7432(4) 0.0417(9) Uani d . 1
H H3 0.1738 0.9935 0.6788 0.050 Uiso calc R 1
C C4 0.2323(5) 0.8648(4) 0.8730(4) 0.0392(9) Uani d . 1
C C5 0.2548(5) 0.7300(4) 0.9738(4) 0.0387(9) Uani d . 1
H H5 0.2754 0.7077 1.0607 0.046 Uiso calc R 1
C C6 0.2453(5) 0.6287(4) 0.9399(3) 0.0325(8) Uani d . 1
C C7 0.2548(5) 0.4811(4) 1.0196(4) 0.0344(8) Uani d . 1
C C8 0.2774(5) 0.3929(4) 1.1564(4) 0.0385(9) Uani d . 1
H H8 0.2907 0.4264 1.2139 0.046 Uiso calc R 1
C C9 0.2791(6) 0.2555(4) 1.2018(4) 0.0434(10) Uani d . 1
C C10 0.2593(6) 0.2020(4) 1.1177(4) 0.0496(11) Uani d . 1
H H10 0.2629 0.1076 1.1523 0.059 Uiso calc R 1
C C11 0.2345(6) 0.2894(4) 0.9841(4) 0.0452(10) Uani d . 1
H H11 0.2190 0.2556 0.9275 0.054 Uiso calc R 1
C C12 0.2330(5) 0.4290(4) 0.9351(4) 0.0343(8) Uani d . 1
C C13 0.1767(6) 0.5241(4) 0.6958(4) 0.0410(9) Uani d . 1
C C14 0.2415(6) 0.6166(4) 0.5600(4) 0.0423(9) Uani d . 1
C C15 0.4143(6) 0.6492(4) 0.5361(4) 0.0471(10) Uani d . 1
H H15 0.4888 0.6202 0.6072 0.056 Uiso calc R 1
C C16 0.4772(7) 0.7249(5) 0.4066(4) 0.0567(12) Uani d . 1
H H16 0.5945 0.7455 0.3910 0.068 Uiso calc R 1
C C17 0.3673(8) 0.7695(5) 0.3015(5) 0.0630(13) Uani d . 1
H H17 0.4092 0.8213 0.2149 0.076 Uiso calc R 1
C C18 0.1927(8) 0.7373(5) 0.3243(5) 0.0656(14) Uani d . 1
H H18 0.1173 0.7689 0.2530 0.079 Uiso calc R 1
C C19 0.1314(7) 0.6585(5) 0.4528(4) 0.0525(11) Uani d . 1
H H19 0.0174 0.6334 0.4678 0.063 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'
O O 0.0106 0.0060 '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
C13 N1 C12 123.3(3)
C13 N1 C1 128.6(3)
C12 N1 C1 107.6(3)
C2 C1 C6 120.4(3)
C2 C1 N1 130.6(3)
C6 C1 N1 108.7(3)
C3 C2 C1 117.8(3)
C3 C2 H2 121.1
C1 C2 H2 121.1
C2 C3 C4 121.2(4)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 122.0(4)
C5 C4 Br1 119.1(3)
C3 C4 Br1 118.9(3)
C4 C5 C6 117.0(3)
C4 C5 H5 121.5
C6 C5 H5 121.5
C5 C6 C1 121.4(3)
C5 C6 C7 131.6(3)
C1 C6 C7 107.0(3)
C12 C7 C8 120.4(3)
C12 C7 C6 107.8(3)
C8 C7 C6 131.7(3)
C9 C8 C7 117.3(3)
C9 C8 H8 121.4
C7 C8 H8 121.4
C8 C9 C10 122.8(4)
C8 C9 Br2 119.2(3)
C10 C9 Br2 118.0(3)
C11 C10 C9 119.7(4)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 118.9(4)
C10 C11 H11 120.6
C12 C11 H11 120.6
C11 C12 C7 121.0(3)
C11 C12 N1 130.2(3)
C7 C12 N1 108.8(3)
O1 C13 N1 119.8(4)
O1 C13 C14 122.1(4)
N1 C13 C14 118.0(3)
C15 C14 C19 119.6(4)
C15 C14 C13 122.1(3)
C19 C14 C13 117.9(4)
C14 C15 C16 120.3(4)
C14 C15 H15 119.9
C16 C15 H15 119.9
C17 C16 C15 120.2(4)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C18 120.0(5)
C16 C17 H17 120.0
C18 C17 H17 120.0
C19 C18 C17 120.1(4)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C14 119.7(4)
C18 C19 H19 120.2
C14 C19 H19 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.900(4)
Br2 C9 1.903(4)
O1 C13 1.210(4)
N1 C13 1.402(5)
N1 C12 1.411(5)
N1 C1 1.417(4)
C1 C2 1.391(5)
C1 C6 1.406(5)
C2 C3 1.373(5)
C2 H2 0.9300
C3 C4 1.396(6)
C3 H3 0.9300
C4 C5 1.375(5)
C5 C6 1.387(5)
C5 H5 0.9300
C6 C7 1.444(5)
C7 C12 1.397(5)
C7 C8 1.400(5)
C8 C9 1.368(5)
C8 H8 0.9300
C9 C10 1.400(6)
C10 C11 1.372(6)
C10 H10 0.9300
C11 C12 1.385(5)
C11 H11 0.9300
C13 C14 1.488(6)
C14 C15 1.380(6)
C14 C19 1.396(6)
C15 C16 1.387(6)
C15 H15 0.9300
C16 C17 1.369(6)
C16 H16 0.9300
C17 C18 1.392(7)
C17 H17 0.9300
C18 C19 1.383(7)
C18 H18 0.9300
C19 H19 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11 Br1 1_545 0.93 2.82 3.600(6) 143 yes
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
C13 N1 C1 C2 0.0(7)
C12 N1 C1 C2 -172.4(4)
C13 N1 C1 C6 174.0(4)
C12 N1 C1 C6 1.6(4)
C6 C1 C2 C3 4.0(5)
N1 C1 C2 C3 177.4(4)
C1 C2 C3 C4 0.1(6)
C2 C3 C4 C5 -3.4(6)
C2 C3 C4 Br1 177.0(3)
C3 C4 C5 C6 2.3(6)
Br1 C4 C5 C6 -178.1(3)
C4 C5 C6 C1 1.9(5)
C4 C5 C6 C7 -177.1(4)
C2 C1 C6 C5 -5.1(6)
N1 C1 C6 C5 -179.9(3)
C2 C1 C6 C7 174.1(3)
N1 C1 C6 C7 -0.6(4)
C5 C6 C7 C12 178.6(4)
C1 C6 C7 C12 -0.6(4)
C5 C6 C7 C8 -0.4(7)
C1 C6 C7 C8 -179.5(4)
C12 C7 C8 C9 0.7(5)
C6 C7 C8 C9 179.5(4)
C7 C8 C9 C10 -0.1(6)
C7 C8 C9 Br2 -179.2(3)
C8 C9 C10 C11 -0.8(6)
Br2 C9 C10 C11 178.3(3)
C9 C10 C11 C12 1.1(6)
C10 C11 C12 C7 -0.5(6)
C10 C11 C12 N1 178.2(4)
C8 C7 C12 C11 -0.4(6)
C6 C7 C12 C11 -179.5(3)
C8 C7 C12 N1 -179.4(3)
C6 C7 C12 N1 1.6(4)
C13 N1 C12 C11 6.3(6)
C1 N1 C12 C11 179.2(4)
C13 N1 C12 C7 -174.9(4)
C1 N1 C12 C7 -2.0(4)
C12 N1 C13 O1 22.9(6)
C1 N1 C13 O1 -148.5(4)
C12 N1 C13 C14 -153.9(4)
C1 N1 C13 C14 34.8(6)
O1 C13 C14 C15 -137.1(5)
N1 C13 C14 C15 39.5(6)
O1 C13 C14 C19 36.0(6)
N1 C13 C14 C19 -147.4(4)
C19 C14 C15 C16 1.0(6)
C13 C14 C15 C16 174.0(4)
C14 C15 C16 C17 0.8(7)
C15 C16 C17 C18 -0.8(8)
C16 C17 C18 C19 -1.0(8)
C17 C18 C19 C14 2.8(8)
C15 C14 C19 C18 -2.8(7)
C13 C14 C19 C18 -176.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128634
