#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/99/2219904.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_2219904
loop_
_publ_author_name
'Gagnon, Eric'
'Laliberté, Dominic'
_publ_section_title
;
 2,7-Dibromo-9-octyl-9H-carbazole
;
_journal_coeditor_code           IS2343
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2147
_journal_paper_doi               10.1107/S1600536808032121
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C20 H23 Br2 N'
_chemical_formula_moiety         'C20 H23 Br2 N'
_chemical_formula_sum            'C20 H23 Br2 N'
_chemical_formula_weight         437.21
_chemical_name_systematic
;
2,7-Dibromo-9-octyl-9H-carbazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 95.9450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7256(4)
_cell_length_b                   4.65780(10)
_cell_length_c                   19.7236(4)
_cell_measurement_reflns_used    20371
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.78
_cell_measurement_theta_min      2.94
_cell_volume                     1893.79(7)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Material Studio (Accelrys, 2005)
;
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30701
_diffrn_reflns_theta_full        68.17
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_min         4.29
_diffrn_standards_decay_%        9.40
_diffrn_standards_interval_time  900
_diffrn_standards_number         136
_exptl_absorpt_coefficient_mu    5.404
_exptl_absorpt_correction_T_max  0.8056
_exptl_absorpt_correction_T_min  0.6330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.385
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0302
_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)+(0.0431P)²+0.9966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                3158
_reflns_number_total             3301
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2343.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (48
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (87
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (46
times).

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (48
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (87
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (46
times).

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219904
_cod_database_fobs_code          2219904
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br Br1 0.277870(14) 0.91023(7) 0.562136(14) 0.05940(12) Uani d . 1
Br Br2 0.056608(12) 0.45377(7) 0.073002(13) 0.05584(12) Uani d . 1
C C1 0.23693(9) 0.8734(4) 0.42106(11) 0.0366(5) Uani d . 1
H H1 0.2690 1.0155 0.4159 0.044 Uiso calc R 1
C C2 0.22615(11) 0.7662(5) 0.48414(11) 0.0411(5) Uani d . 1
C C3 0.17985(12) 0.5585(5) 0.49381(12) 0.0452(5) Uani d . 1
H H3 0.1744 0.4921 0.5384 0.054 Uiso calc R 1
C C4 0.14194(11) 0.4495(4) 0.43831(12) 0.0405(5) Uani d . 1
H H4 0.1100 0.3080 0.4443 0.049 Uiso calc R 1
C C5 0.07350(9) 0.2906(4) 0.27976(11) 0.0368(5) Uani d . 1
H H5 0.0533 0.1671 0.3096 0.044 Uiso calc R 1
C C6 0.05563(9) 0.2808(4) 0.21101(12) 0.0396(5) Uani d . 1
H H6 0.0231 0.1502 0.1930 0.047 Uiso calc R 1
C C7 0.08542(10) 0.4637(4) 0.16739(12) 0.0377(5) Uani d . 1
C C8 0.13427(9) 0.6544(4) 0.19041(10) 0.0340(4) Uani d . 1
H H8 0.1547 0.7739 0.1600 0.041 Uiso calc R 1
C C9 0.15163(8) 0.6612(4) 0.26027(10) 0.0296(4) Uani d . 1
C C10 0.12158(9) 0.4832(4) 0.30598(11) 0.0313(4) Uani d . 1
C C11 0.15084(9) 0.5491(4) 0.37300(11) 0.0333(4) Uani d . 1
C C12 0.19845(9) 0.7622(4) 0.36566(10) 0.0317(4) Uani d . 1
C C13 0.24263(9) 1.0219(4) 0.26789(10) 0.0312(4) Uani d . 1
H H13A 0.2547 1.1795 0.3004 0.037 Uiso calc R 1
H H13B 0.2208 1.1080 0.2257 0.037 Uiso calc R 1
C C14 0.30385(9) 0.8674(4) 0.25132(11) 0.0319(4) Uani d . 1
H H14A 0.3277 0.7976 0.2942 0.038 Uiso calc R 1
H H14B 0.2914 0.6981 0.2226 0.038 Uiso calc R 1
C C15 0.34861(9) 1.0575(4) 0.21437(11) 0.0327(4) Uani d . 1
H H15A 0.3241 1.1362 0.1728 0.039 Uiso calc R 1
H H15B 0.3631 1.2212 0.2442 0.039 Uiso calc R 1
C C16 0.40776(9) 0.8980(4) 0.19451(11) 0.0341(4) Uani d . 1
H H16A 0.3931 0.7254 0.1680 0.041 Uiso calc R 1
H H16B 0.4339 0.8325 0.2365 0.041 Uiso calc R 1
C C17 0.45074(10) 1.0767(4) 0.15261(12) 0.0364(5) Uani d . 1
H H17A 0.4241 1.1515 0.1119 0.044 Uiso calc R 1
H H17B 0.4676 1.2434 0.1801 0.044 Uiso calc R 1
C C18 0.50750(10) 0.9090(4) 0.12985(12) 0.0396(5) Uani d . 1
H H18A 0.5331 0.8288 0.1706 0.048 Uiso calc R 1
H H18B 0.4904 0.7457 0.1013 0.048 Uiso calc R 1
C C19 0.55238(10) 1.0841(5) 0.08983(13) 0.0442(5) Uani d . 1
H H19A 0.5698 1.2473 0.1182 0.053 Uiso calc R 1
H H19B 0.5270 1.1638 0.0488 0.053 Uiso calc R 1
C C20 0.60875(12) 0.9104(6) 0.06785(16) 0.0586(7) Uani d . 1
H H20A 0.6350 0.8366 0.1083 0.088 Uiso calc R 1
H H20B 0.6356 1.0334 0.0418 0.088 Uiso calc R 1
H H20C 0.5920 0.7494 0.0393 0.088 Uiso calc R 1
N N1 0.19774(7) 0.8298(3) 0.29719(8) 0.0309(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 C12 116.24(19) n
C2 C1 H1 121.9 n
C12 C1 H1 121.9 n
C1 C2 C3 123.7(2) n
C1 C2 Br1 118.09(17) n
C3 C2 Br1 118.25(17) n
C4 C3 C2 119.5(2) n
C4 C3 H3 120.2 n
C2 C3 H3 120.2 n
C3 C4 C11 119.4(2) n
C3 C4 H4 120.3 n
C11 C4 H4 120.3 n
C6 C5 C10 119.78(18) n
C6 C5 H5 120.1 n
C10 C5 H5 120.1 n
C5 C6 C7 119.84(19) n
C5 C6 H6 120.1 n
C7 C6 H6 120.1 n
C8 C7 C6 122.8(2) n
C8 C7 Br2 118.81(16) n
C6 C7 Br2 118.36(16) n
C7 C8 C9 116.41(18) n
C7 C8 H8 121.8 n
C9 C8 H8 121.8 n
N1 C9 C8 128.98(17) n
N1 C9 C10 108.81(17) n
C8 C9 C10 122.21(18) n
C5 C10 C9 118.90(19) n
C5 C10 C11 134.20(18) n
C9 C10 C11 106.90(17) n
C4 C11 C12 119.1(2) n
C4 C11 C10 134.14(19) n
C12 C11 C10 106.81(17) n
C1 C12 N1 129.14(18) n
C1 C12 C11 122.11(18) n
N1 C12 C11 108.76(18) n
N1 C13 C14 112.13(15) n
N1 C13 H13A 109.2 n
C14 C13 H13A 109.2 n
N1 C13 H13B 109.2 n
C14 C13 H13B 109.2 n
H13A C13 H13B 107.9 n
C15 C14 C13 113.00(15) n
C15 C14 H14A 109.0 n
C13 C14 H14A 109.0 n
C15 C14 H14B 109.0 n
C13 C14 H14B 109.0 n
H14A C14 H14B 107.8 n
C16 C15 C14 112.77(15) n
C16 C15 H15A 109.0 n
C14 C15 H15A 109.0 n
C16 C15 H15B 109.0 n
C14 C15 H15B 109.0 n
H15A C15 H15B 107.8 n
C15 C16 C17 113.92(16) n
C15 C16 H16A 108.8 n
C17 C16 H16A 108.8 n
C15 C16 H16B 108.8 n
C17 C16 H16B 108.8 n
H16A C16 H16B 107.7 n
C18 C17 C16 113.20(16) n
C18 C17 H17A 108.9 n
C16 C17 H17A 108.9 n
C18 C17 H17B 108.9 n
C16 C17 H17B 108.9 n
H17A C17 H17B 107.8 n
C19 C18 C17 114.38(17) n
C19 C18 H18A 108.7 n
C17 C18 H18A 108.7 n
C19 C18 H18B 108.7 n
C17 C18 H18B 108.7 n
H18A C18 H18B 107.6 n
C18 C19 C20 113.13(19) n
C18 C19 H19A 109.0 n
C20 C19 H19A 109.0 n
C18 C19 H19B 109.0 n
C20 C19 H19B 109.0 n
H19A C19 H19B 107.8 n
C19 C20 H20A 109.5 n
C19 C20 H20B 109.5 n
H20A C20 H20B 109.5 n
C19 C20 H20C 109.5 n
H20A C20 H20C 109.5 n
H20B C20 H20C 109.5 n
C9 N1 C12 108.71(15) n
C9 N1 C13 125.15(16) n
C12 N1 C13 125.82(17) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 1.904(2) n
Br2 C7 1.896(2) n
C1 C2 1.380(3) n
C1 C12 1.385(3) n
C1 H1 0.9500 n
C2 C3 1.390(3) n
C3 C4 1.376(4) n
C3 H3 0.9500 n
C4 C11 1.399(3) n
C4 H4 0.9500 n
C5 C6 1.369(3) n
C5 C10 1.399(3) n
C5 H5 0.9500 n
C6 C7 1.399(3) n
C6 H6 0.9500 n
C7 C8 1.387(3) n
C8 C9 1.388(3) n
C8 H8 0.9500 n
C9 N1 1.384(3) n
C9 C10 1.416(3) n
C10 C11 1.429(3) n
C11 C12 1.417(3) n
C12 N1 1.385(2) n
C13 N1 1.453(2) n
C13 C14 1.523(2) n
C13 H13A 0.9900 n
C13 H13B 0.9900 n
C14 C15 1.522(2) n
C14 H14A 0.9900 n
C14 H14B 0.9900 n
C15 C16 1.519(3) n
C15 H15A 0.9900 n
C15 H15B 0.9900 n
C16 C17 1.524(3) n
C16 H16A 0.9900 n
C16 H16B 0.9900 n
C17 C18 1.518(3) n
C17 H17A 0.9900 n
C17 H17B 0.9900 n
C18 C19 1.518(3) n
C18 H18A 0.9900 n
C18 H18B 0.9900 n
C19 C20 1.520(3) n
C19 H19A 0.9900 n
C19 H19B 0.9900 n
C20 H20A 0.9800 n
C20 H20B 0.9800 n
C20 H20C 0.9800 n
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
C13 H13A Cg1 1_565 0.98 2.96 3.582(2) 121 y
C13 H13A Cg2 1_565 0.98 2.99 3.566(2) 119 y
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
C12 C1 C2 C3 0.0(3) n
C12 C1 C2 Br1 179.77(14) n
C1 C2 C3 C4 0.0(3) n
Br1 C2 C3 C4 -179.72(16) n
C2 C3 C4 C11 0.3(3) n
C10 C5 C6 C7 -0.1(3) n
C5 C6 C7 C8 1.5(3) n
C5 C6 C7 Br2 -177.43(14) n
C6 C7 C8 C9 -1.5(3) n
Br2 C7 C8 C9 177.42(13) n
C7 C8 C9 N1 -179.35(17) n
C7 C8 C9 C10 0.2(3) n
C6 C5 C10 C9 -1.1(3) n
C6 C5 C10 C11 179.62(19) n
N1 C9 C10 C5 -179.27(16) n
C8 C9 C10 C5 1.1(3) n
N1 C9 C10 C11 0.18(19) n
C8 C9 C10 C11 -179.46(16) n
C3 C4 C11 C12 -0.5(3) n
C3 C4 C11 C10 179.1(2) n
C5 C10 C11 C4 -1.2(4) n
C9 C10 C11 C4 179.4(2) n
C5 C10 C11 C12 178.5(2) n
C9 C10 C11 C12 -0.84(19) n
C2 C1 C12 N1 179.21(18) n
C2 C1 C12 C11 -0.4(3) n
C4 C11 C12 C1 0.6(3) n
C10 C11 C12 C1 -179.15(17) n
C4 C11 C12 N1 -179.03(16) n
C10 C11 C12 N1 1.2(2) n
N1 C13 C14 C15 174.47(17) n
C13 C14 C15 C16 -176.84(18) n
C14 C15 C16 C17 175.50(18) n
C15 C16 C17 C18 -176.75(19) n
C16 C17 C18 C19 -178.2(2) n
C17 C18 C19 C20 179.9(2) n
C8 C9 N1 C12 -179.81(18) n
C10 C9 N1 C12 0.58(19) n
C8 C9 N1 C13 -6.1(3) n
C10 C9 N1 C13 174.33(16) n
C1 C12 N1 C9 179.27(18) n
C11 C12 N1 C9 -1.12(19) n
C1 C12 N1 C13 5.6(3) n
C11 C12 N1 C13 -174.82(16) n
C14 C13 N1 C9 -86.0(2) n
C14 C13 N1 C12 86.7(2) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740902
