#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225353.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_2225353
loop_
_publ_author_name
'Xu, Guo-Yi'
'Geng, Wen-Qian'
'Zhou, Hong-Ping'
_publ_section_title
;
 9-Ethyl-3,6-bis(5-iodo-2-thienyl)-9H-carbazole
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o571
_journal_paper_doi               10.1107/S1600536810004484
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H15 I2 N S2'
_chemical_formula_moiety         'C22 H15 I2 N S2'
_chemical_formula_sum            'C22 H15 I2 N S2'
_chemical_formula_weight         611.29
_chemical_name_systematic
;
9-Ethyl-3,6-bis(5-iodo-2-thienyl)-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                90.00
_cell_angle_beta                 107.313(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.637(3)
_cell_length_b                   7.814(2)
_cell_length_c                   26.687(7)
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.37
_cell_volume                     2117.7(10)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 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     0.71069
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17471
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    3.174
_exptl_absorpt_correction_T_max  0.7419
_exptl_absorpt_correction_T_min  0.4493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.786
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0360
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                3065
_reflns_number_total             3738
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            rk2188.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_structure_factor_coef' value ' Fsqd' changed to
'Fsqd' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

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

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_structure_factor_coef' value ' Fsqd' changed
to 'Fsqd' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

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               2225353
_cod_database_fobs_code          2225353
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.25459(4) 1.46648(5) 1.073693(15) 0.0711(2) Uani d . 1 . .
I I2 -0.70485(4) 0.47106(5) 0.685869(19) 0.0818(2) Uani d . 1 . .
S S1 0.28672(13) 1.0941(2) 1.02087(5) 0.0797(5) Uani d . 1 . .
S S2 -0.39715(12) 0.45973(15) 0.75996(5) 0.0589(3) Uani d . 1 . .
N N1 0.2462(4) 0.3710(7) 0.87990(17) 0.0768(13) Uani d . 1 . .
C C1 0.3499(4) 0.6105(8) 0.94135(18) 0.0651(13) Uani d . 1 . .
H H1 0.4337 0.5626 0.9523 0.078 Uiso calc R 1 . .
C C2 0.3241(4) 0.7652(8) 0.96071(18) 0.0631(12) Uani d . 1 . .
H H2 0.3925 0.8228 0.9847 0.076 Uiso calc R 1 . .
C C3 0.1979(4) 0.8397(7) 0.94558(16) 0.0550(11) Uani d . 1 . .
C C4 0.0960(4) 0.7564(6) 0.90838(16) 0.0532(10) Uani d . 1 . .
H H4 0.0125 0.8050 0.8974 0.064 Uiso calc R 1 . .
C C5 -0.0883(5) 0.4929(6) 0.81521(18) 0.0513(11) Uani d . 1 . .
H H5 -0.1440 0.5816 0.8182 0.062 Uiso calc R 1 . .
C C6 -0.1344(4) 0.3655(6) 0.77807(17) 0.0543(11) Uani d . 1 . .
C C7 -0.0498(5) 0.2311(7) 0.7748(2) 0.0721(14) Uani d . 1 . .
H H7 -0.0812 0.1450 0.7502 0.087 Uiso calc R 1 . .
C C8 0.0776(5) 0.2224(8) 0.8067(2) 0.0792(16) Uani d . 1 . .
H H8 0.1326 0.1332 0.8035 0.095 Uiso calc R 1 . .
C C9 0.1219(5) 0.3487(7) 0.8434(2) 0.0674(13) Uani d . 1 . .
C C10 0.0396(5) 0.4886(6) 0.84774(19) 0.0526(11) Uani d . 1 . .
C C11 0.1197(4) 0.6004(6) 0.88770(16) 0.0504(10) Uani d . 1 . .
C C12 0.2465(5) 0.5279(7) 0.9049(2) 0.0612(13) Uani d . 1 . .
C C13 0.3602(6) 0.2581(11) 0.8866(3) 0.101(2) Uani d . 1 . .
H H13A 0.4207 0.2705 0.9217 0.121 Uiso calc R 1 . .
H H13B 0.3318 0.1397 0.8817 0.121 Uiso calc R 1 . .
C C14 0.4210(8) 0.3038(11) 0.8499(3) 0.120(3) Uani d . 1 . .
H H14A 0.4396 0.4243 0.8525 0.180 Uiso calc R 1 . .
H H14B 0.3641 0.2781 0.8154 0.180 Uiso calc R 1 . .
H H14C 0.5018 0.2411 0.8560 0.180 Uiso calc R 1 . .
C C15 0.1743(5) 1.0054(6) 0.96736(18) 0.0521(11) Uani d . 1 . .
C C16 0.0690(6) 1.1130(8) 0.9511(3) 0.0900(19) Uani d . 1 . .
H H16 -0.0044 1.0889 0.9227 0.108 Uiso calc R 1 . .
C C17 0.0809(6) 1.2599(9) 0.9803(3) 0.098(2) Uani d . 1 . .
H H17 0.0165 1.3445 0.9732 0.117 Uiso calc R 1 . .
C C18 0.1926(4) 1.2712(6) 1.01974(17) 0.0570(11) Uani d . 1 . .
C C19 -0.2682(4) 0.3707(6) 0.74207(17) 0.0520(10) Uani d . 1 . .
C C20 -0.3136(5) 0.3054(7) 0.69241(19) 0.0640(13) Uani d . 1 . .
H H20 -0.2592 0.2528 0.6754 0.077 Uiso calc R 1 . .
C C21 -0.4518(5) 0.3255(7) 0.6691(2) 0.0672(13) Uani d . 1 . .
H H21 -0.4972 0.2872 0.6356 0.081 Uiso calc R 1 . .
C C22 -0.5089(4) 0.4058(6) 0.7009(2) 0.0599(12) 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 0.0033 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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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
C18 S1 C15 . . 93.1(2) ?
C22 S2 C19 . . 92.1(2) ?
C12 N1 C9 . . 108.0(4) ?
C12 N1 C13 . . 125.9(5) ?
C9 N1 C13 . . 125.8(5) ?
C2 C1 C12 . . 117.8(4) ?
C2 C1 H1 . . 121.1 ?
C12 C1 H1 . . 121.1 ?
C1 C2 C3 . . 122.5(5) ?
C1 C2 H2 . . 118.8 ?
C3 C2 H2 . . 118.8 ?
C4 C3 C2 . . 119.0(5) ?
C4 C3 C15 . . 120.3(4) ?
C2 C3 C15 . . 120.8(4) ?
C11 C4 C3 . . 119.8(4) ?
C11 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C10 C5 C6 . . 120.3(4) ?
C10 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.0(4) ?
C5 C6 C19 . . 121.2(4) ?
C7 C6 C19 . . 119.8(4) ?
C8 C7 C6 . . 122.2(5) ?
C8 C7 H7 . . 118.9 ?
C6 C7 H7 . . 118.9 ?
C7 C8 C9 . . 118.2(5) ?
C7 C8 H8 . . 120.9 ?
C9 C8 H8 . . 120.9 ?
C8 C9 N1 . . 129.7(5) ?
C8 C9 C10 . . 121.4(5) ?
N1 C9 C10 . . 108.9(4) ?
C5 C10 C9 . . 118.8(4) ?
C5 C10 C11 . . 134.8(4) ?
C9 C10 C11 . . 106.4(4) ?
C4 C11 C12 . . 119.5(4) ?
C4 C11 C10 . . 133.3(4) ?
C12 C11 C10 . . 107.1(4) ?
C1 C12 N1 . . 129.1(4) ?
C1 C12 C11 . . 121.5(5) ?
N1 C12 C11 . . 109.5(4) ?
C14 C13 N1 . . 107.7(7) ?
C14 C13 H13A . . 110.2 ?
N1 C13 H13A . . 110.2 ?
C14 C13 H13B . . 110.2 ?
N1 C13 H13B . . 110.2 ?
H13A C13 H13B . . 108.5 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C3 . . 129.6(5) ?
C16 C15 S1 . . 108.6(4) ?
C3 C15 S1 . . 121.8(3) ?
C15 C16 C17 . . 114.0(5) ?
C15 C16 H16 . . 123.0 ?
C17 C16 H16 . . 123.0 ?
C18 C17 C16 . . 114.4(5) ?
C18 C17 H17 . . 122.8 ?
C16 C17 H17 . . 122.8 ?
C17 C18 S1 . . 109.9(4) ?
C17 C18 I1 . . 128.5(4) ?
S1 C18 I1 . . 121.6(2) ?
C20 C19 C6 . . 128.3(4) ?
C20 C19 S2 . . 109.8(3) ?
C6 C19 S2 . . 121.9(3) ?
C19 C20 C21 . . 113.7(4) ?
C19 C20 H20 . . 123.1 ?
C21 C20 H20 . . 123.1 ?
C22 C21 C20 . . 112.2(4) ?
C22 C21 H21 . . 123.9 ?
C20 C21 H21 . . 123.9 ?
C21 C22 S2 . . 112.1(4) ?
C21 C22 I2 . . 127.9(4) ?
S2 C22 I2 . . 120.0(3) ?
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
I1 C18 . 2.066(5) ?
I2 C22 . 2.066(5) ?
S1 C18 . 1.703(5) ?
S1 C15 . 1.713(5) ?
S2 C22 . 1.720(5) ?
S2 C19 . 1.727(4) ?
N1 C12 . 1.395(7) ?
N1 C9 . 1.400(6) ?
N1 C13 . 1.466(8) ?
C1 C2 . 1.374(8) ?
C1 C12 . 1.392(7) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.407(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.394(6) ?
C3 C15 . 1.471(7) ?
C4 C11 . 1.392(7) ?
C4 H4 . 0.9300 ?
C5 C10 . 1.380(7) ?
C5 C6 . 1.387(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.403(7) ?
C6 C19 . 1.462(6) ?
C7 C8 . 1.371(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.372(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.427(7) ?
C10 C11 . 1.444(7) ?
C11 C12 . 1.408(6) ?
C13 C14 . 1.373(9) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.364(7) ?
C16 C17 . 1.373(9) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.336(7) ?
C17 H17 . 0.9300 ?
C19 C20 . 1.367(6) ?
C20 C21 . 1.425(7) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.338(7) ?
C21 H21 . 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
C17 H17 I1 3_587 0.93 3.149 4.040(9) 161.1
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 C1 C2 C3 . . . . 1.0(8) ?
C1 C2 C3 C4 . . . . -2.0(8) ?
C1 C2 C3 C15 . . . . 179.8(5) ?
C2 C3 C4 C11 . . . . 1.3(7) ?
C15 C3 C4 C11 . . . . 179.5(4) ?
C10 C5 C6 C7 . . . . 1.2(7) ?
C10 C5 C6 C19 . . . . -178.0(4) ?
C5 C6 C7 C8 . . . . -0.9(8) ?
C19 C6 C7 C8 . . . . 178.3(5) ?
C6 C7 C8 C9 . . . . 1.2(9) ?
C7 C8 C9 N1 . . . . -179.2(6) ?
C7 C8 C9 C10 . . . . -1.7(9) ?
C12 N1 C9 C8 . . . . 174.0(6) ?
C13 N1 C9 C8 . . . . 0.0(11) ?
C12 N1 C9 C10 . . . . -3.7(6) ?
C13 N1 C9 C10 . . . . -177.7(6) ?
C6 C5 C10 C9 . . . . -1.8(7) ?
C6 C5 C10 C11 . . . . 176.5(5) ?
C8 C9 C10 C5 . . . . 2.1(8) ?
N1 C9 C10 C5 . . . . 180.0(5) ?
C8 C9 C10 C11 . . . . -176.6(5) ?
N1 C9 C10 C11 . . . . 1.3(6) ?
C3 C4 C11 C12 . . . . 0.4(7) ?
C3 C4 C11 C10 . . . . -176.4(5) ?
C5 C10 C11 C4 . . . . 0.2(9) ?
C9 C10 C11 C4 . . . . 178.5(5) ?
C5 C10 C11 C12 . . . . -176.8(5) ?
C9 C10 C11 C12 . . . . 1.5(5) ?
C2 C1 C12 N1 . . . . -179.3(5) ?
C2 C1 C12 C11 . . . . 0.7(8) ?
C9 N1 C12 C1 . . . . -175.2(6) ?
C13 N1 C12 C1 . . . . -1.2(10) ?
C9 N1 C12 C11 . . . . 4.7(7) ?
C13 N1 C12 C11 . . . . 178.7(6) ?
C4 C11 C12 C1 . . . . -1.4(7) ?
C10 C11 C12 C1 . . . . 176.1(5) ?
C4 C11 C12 N1 . . . . 178.6(4) ?
C10 C11 C12 N1 . . . . -3.9(6) ?
C12 N1 C13 C14 . . . . -90.0(8) ?
C9 N1 C13 C14 . . . . 83.0(9) ?
C4 C3 C15 C16 . . . . -12.0(8) ?
C2 C3 C15 C16 . . . . 166.2(6) ?
C4 C3 C15 S1 . . . . 168.4(4) ?
C2 C3 C15 S1 . . . . -13.4(6) ?
C18 S1 C15 C16 . . . . -0.7(5) ?
C18 S1 C15 C3 . . . . 179.0(4) ?
C3 C15 C16 C17 . . . . -178.9(6) ?
S1 C15 C16 C17 . . . . 0.8(8) ?
C15 C16 C17 C18 . . . . -0.5(10) ?
C16 C17 C18 S1 . . . . 0.0(8) ?
C16 C17 C18 I1 . . . . 179.7(5) ?
C15 S1 C18 C17 . . . . 0.4(5) ?
C15 S1 C18 I1 . . . . -179.4(3) ?
C5 C6 C19 C20 . . . . 151.0(5) ?
C7 C6 C19 C20 . . . . -28.1(8) ?
C5 C6 C19 S2 . . . . -31.6(6) ?
C7 C6 C19 S2 . . . . 149.2(4) ?
C22 S2 C19 C20 . . . . 0.6(4) ?
C22 S2 C19 C6 . . . . -177.3(4) ?
C6 C19 C20 C21 . . . . 177.0(5) ?
S2 C19 C20 C21 . . . . -0.6(6) ?
C19 C20 C21 C22 . . . . 0.4(7) ?
C20 C21 C22 S2 . . . . 0.1(6) ?
C20 C21 C22 I2 . . . . 178.7(4) ?
C19 S2 C22 C21 . . . . -0.4(4) ?
C19 S2 C22 I2 . . . . -179.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744454
