#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/43/2234353.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_2234353
loop_
_publ_author_name
'Xie, Yu-Zhong'
'Jin, Jing-Yi'
'Jin, Guang-De'
_publ_section_title
;
 3,6-Diiodo-9H-carbazole
;
_journal_coeditor_code           PK2397
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1242
_journal_paper_doi               10.1107/S1600536812012901
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H7 I2 N'
_chemical_formula_moiety         'C12 H7 I2 N'
_chemical_formula_sum            'C12 H7 I2 N'
_chemical_formula_weight         418.99
_chemical_name_common            3,6-diiodo-9H-carbazole
_chemical_name_systematic        3,6-Diiodo-9H-carbazole
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.8823(14)
_cell_length_b                   7.8835(9)
_cell_length_c                   24.835(3)
_cell_measurement_reflns_used    12303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      1.64
_cell_volume                     2326.4(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12303
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.372
_exptl_absorpt_correction_T_max  0.445
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.561
_refine_ls_extinction_coef       0.00021(4)
_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   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0256
_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)+(0.0193P)²+0.8116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0521
_reflns_number_gt                1879
_reflns_number_total             2456
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2397.cif
_cod_data_source_block           I
_cod_database_code               2234353
_cod_database_fobs_code          2234353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_symmetry_multiplicity
C C11 0.7583(3) 0.4740(4) 0.77946(15) 0.0445(9) Uani d . 1 1
H H11 0.8290 0.5240 0.7822 0.053 Uiso calc R 1 1
C C12 0.6978(3) 0.4308(4) 0.82476(14) 0.0406(9) Uani d . 1 1
H H12 0.7277 0.4525 0.8587 0.049 Uiso calc R 1 1
H H1N 0.807(3) 0.511(4) 0.6716(13) 0.032(11) Uiso d . 1 1
I I2 0.35650(2) 0.22435(4) 0.536173(10) 0.06040(11) Uani d . 1 1
I I1 0.50690(2) 0.28678(4) 0.891514(9) 0.04915(10) Uani d . 1 1
N N1 0.7525(3) 0.4684(4) 0.67876(13) 0.0460(8) Uani d . 1 1
C C5 0.4904(3) 0.2882(4) 0.63769(13) 0.0387(8) Uani d . 1 1
H H5 0.4264 0.2467 0.6548 0.046 Uiso calc R 1 1
C C4 0.5818(3) 0.3460(4) 0.66751(12) 0.0333(8) Uani d . 1 1
C C6 0.4967(3) 0.2939(5) 0.58238(14) 0.0432(9) Uani d . 1 1
C C9 0.6766(3) 0.4125(4) 0.64077(14) 0.0402(9) Uani d . 1 1
C C1 0.5918(3) 0.3545(4) 0.82033(13) 0.0373(8) Uani d . 1 1
C C2 0.5437(3) 0.3208(4) 0.77121(13) 0.0357(8) Uani d . 1 1
H H2 0.4730 0.2705 0.7690 0.043 Uiso calc R 1 1
C C3 0.6032(3) 0.3638(4) 0.72449(12) 0.0333(8) Uani d . 1 1
C C8 0.6826(3) 0.4177(5) 0.58496(14) 0.0478(10) Uani d . 1 1
H H8 0.7461 0.4603 0.5677 0.057 Uiso calc R 1 1
C C7 0.5931(3) 0.3587(5) 0.55598(14) 0.0492(10) Uani d . 1 1
H H7 0.5954 0.3612 0.5186 0.059 Uiso calc R 1 1
C C10 0.7105(3) 0.4408(4) 0.72961(14) 0.0375(8) Uani d . 1 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'
I I -0.4742 1.8119 '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
C12 C11 C10 117.9(3)
C12 C11 H11 121.0
C10 C11 H11 121.0
C11 C12 C1 120.8(3)
C11 C12 H12 119.6
C1 C12 H12 119.6
C10 N1 C9 109.9(3)
C10 N1 H1N 127(3)
C9 N1 H1N 123(3)
C6 C5 C4 118.5(3)
C6 C5 H5 120.7
C4 C5 H5 120.7
C5 C4 C9 119.7(3)
C5 C4 C3 133.7(3)
C9 C4 C3 106.6(3)
C5 C6 C7 121.2(3)
C5 C6 I2 119.6(3)
C7 C6 I2 118.9(3)
N1 C9 C8 129.8(3)
N1 C9 C4 108.7(3)
C8 C9 C4 121.5(3)
C2 C1 C12 121.8(3)
C2 C1 I1 119.8(3)
C12 C1 I1 118.3(3)
C1 C2 C3 118.6(3)
C1 C2 H2 120.7
C3 C2 H2 120.7
C2 C3 C10 118.9(3)
C2 C3 C4 134.4(3)
C10 C3 C4 106.7(3)
C7 C8 C9 118.4(4)
C7 C8 H8 120.8
C9 C8 H8 120.8
C8 C7 C6 120.6(3)
C8 C7 H7 119.7
C6 C7 H7 119.7
N1 C10 C11 129.9(3)
N1 C10 C3 108.2(3)
C11 C10 C3 121.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 C12 1.378(5)
C11 C10 1.387(5)
C11 H11 0.9300
C12 C1 1.400(5)
C12 H12 0.9300
I2 C6 2.096(4)
I1 C1 2.104(3)
N1 C10 1.375(4)
N1 C9 1.378(5)
N1 H1N 0.75(3)
C5 C6 1.376(5)
C5 C4 1.391(5)
C5 H5 0.9300
C4 C9 1.409(5)
C4 C3 1.445(4)
C6 C7 1.415(5)
C9 C8 1.389(5)
C1 C2 1.373(4)
C2 C3 1.400(4)
C2 H2 0.9300
C3 C10 1.418(5)
C8 C7 1.366(5)
C8 H8 0.9300
C7 H7 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
C10 C11 C12 C1 0.5(5)
C6 C5 C4 C9 1.7(5)
C6 C5 C4 C3 177.7(4)
C4 C5 C6 C7 -0.8(5)
C4 C5 C6 I2 -175.7(2)
C10 N1 C9 C8 178.7(4)
C10 N1 C9 C4 0.0(4)
C5 C4 C9 N1 177.0(3)
C3 C4 C9 N1 0.0(4)
C5 C4 C9 C8 -1.8(5)
C3 C4 C9 C8 -178.8(3)
C11 C12 C1 C2 -0.4(5)
C11 C12 C1 I1 178.5(3)
C12 C1 C2 C3 0.3(5)
I1 C1 C2 C3 -178.6(2)
C1 C2 C3 C10 -0.2(5)
C1 C2 C3 C4 178.7(4)
C5 C4 C3 C2 4.6(7)
C9 C4 C3 C2 -179.0(4)
C5 C4 C3 C10 -176.4(4)
C9 C4 C3 C10 0.1(4)
N1 C9 C8 C7 -177.6(4)
C4 C9 C8 C7 1.0(5)
C9 C8 C7 C6 -0.1(6)
C5 C6 C7 C8 0.0(6)
I2 C6 C7 C8 174.9(3)
C9 N1 C10 C11 178.8(4)
C9 N1 C10 C3 0.0(4)
C12 C11 C10 N1 -179.0(4)
C12 C11 C10 C3 -0.4(5)
C2 C3 C10 N1 179.1(3)
C4 C3 C10 N1 -0.1(4)
C2 C3 C10 C11 0.3(5)
C4 C3 C10 C11 -178.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2370235
