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#$Date: 2023-03-24 11:30:04 +0200 (Fri, 24 Mar 2023) $
#$Revision: 282038 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106976.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106976
loop_
_publ_author_name
'Yin, Guo-jie'
_publ_section_title
;
 Crystal structure of
 5,5-bis(4-iodophenyl)-5H-cyclopenta[2,1-b:3,4-b′]dipyridine,
 C23H14I2N2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              685
_journal_page_last               686
_journal_paper_doi               10.1515/ncrs-2015-0225
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C23 H14 I2 N2'
_chemical_formula_weight         572.16
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.86217(15)
_cell_length_b                   11.86217(15)
_cell_length_c                   13.9664(3)
_cell_measurement_reflns_used    2194
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6069
_cell_measurement_theta_min      3.1616
_cell_volume                     1965.23(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3918
_diffrn_reflns_theta_full        71.75
_diffrn_reflns_theta_max         71.75
_diffrn_reflns_theta_min         4.89
_exptl_absorpt_coefficient_mu    25.203
_exptl_absorpt_correction_T_max  0.006
_exptl_absorpt_correction_T_min  0.002
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0387
_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)+(0.0641P)²+1.0548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                1815
_reflns_number_total             1893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0225_suppl.cif
_cod_data_source_block           l3
_cod_original_cell_volume        1965.22(5)
_cod_original_sg_symbol_H-M      P41212
_cod_database_code               8106976
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.97978(5) 0.61916(3) 1.04178(3) 0.06421(19) Uani 1 1 d . . .
C10 C 0.9717(5) 0.7511(4) 0.9439(4) 0.0407(11) Uani 1 1 d . . .
C9 C 0.8772(5) 0.7716(5) 0.8921(4) 0.0470(12) Uani 1 1 d . . .
H9 H 0.8148 0.7250 0.8996 0.056 Uiso 1 1 calc R . .
C12 C 1.0623(5) 0.9075(5) 0.8677(5) 0.0508(14) Uani 1 1 d . . .
H12 H 1.1263 0.9515 0.8584 0.061 Uiso 1 1 calc R . .
C11 C 1.0658(6) 0.8199(6) 0.9330(5) 0.0505(13) Uani 1 1 d . . .
H11 H 1.1304 0.8070 0.9692 0.061 Uiso 1 1 calc R . .
C4 C 0.9532(4) 1.1422(4) 0.8130(4) 0.0371(10) Uani 1 1 d . . .
C7 C 0.9647(4) 0.9312(4) 0.8157(4) 0.0373(10) Uani 1 1 d . . .
C8 C 0.8718(5) 0.8625(5) 0.8268(4) 0.0442(11) Uani 1 1 d . . .
H8 H 0.8064 0.8758 0.7918 0.053 Uiso 1 1 calc R . .
C6 C 0.9636(4) 1.0364(4) 0.7500 0.0380(14) Uani 1 2 d S . .
C5 C 0.8557(4) 1.2018(4) 0.7911(4) 0.0394(10) Uani 1 1 d . . .
C2 C 0.9842(6) 1.2792(5) 0.9324(5) 0.0519(14) Uani 1 1 d . . .
H2 H 1.0282 1.3103 0.9808 0.062 Uiso 1 1 calc R . .
C1 C 0.8827(6) 1.3301(6) 0.9067(5) 0.0542(15) Uani 1 1 d . . .
H1 H 0.8587 1.3925 0.9415 0.065 Uiso 1 1 calc R . .
C3 C 1.0197(5) 1.1826(5) 0.8859(4) 0.0438(11) Uani 1 1 d . . .
H3 H 1.0861 1.1463 0.9033 0.053 Uiso 1 1 calc R . .
N1 N 0.8182(5) 1.2939(4) 0.8348(4) 0.0486(11) Uani 1 1 d . . .
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'
I I -0.3257 6.8362 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C9 C10 C11 119.9(5) . .
C9 C10 I1 121.6(4) . .
C11 C10 I1 118.4(5) . .
C10 C9 C8 121.3(5) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
C11 C12 C7 121.3(6) . .
C11 C12 H12 119.4 . .
C7 C12 H12 119.4 . .
C12 C11 C10 119.3(6) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C3 C4 C5 117.6(5) . .
C3 C4 C6 131.5(5) . .
C5 C4 C6 110.9(5) . .
C8 C7 C12 119.0(5) . .
C8 C7 C6 122.4(5) . .
C12 C7 C6 118.5(5) . .
C7 C8 C9 119.1(6) . .
C7 C8 H8 120.4 . .
C9 C8 H8 120.4 . .
C4 C6 C4 101.3(6) . 8_776
C4 C6 C7 114.2(3) . 8_776
C4 C6 C7 108.6(3) 8_776 8_776
C4 C6 C7 108.6(3) . .
C4 C6 C7 114.2(3) 8_776 .
C7 C6 C7 109.7(6) 8_776 .
N1 C5 C4 126.6(5) . .
N1 C5 C5 125.0(3) . 8_776
C4 C5 C5 108.4(3) . 8_776
C3 C2 C1 120.1(6) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
N1 C1 C2 123.3(6) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C4 C3 C2 117.5(6) . .
C4 C3 H3 121.2 . .
C2 C3 H3 121.2 . .
C5 N1 C1 114.8(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C10 2.080(5) .
C10 C9 1.356(9) .
C10 C11 1.392(9) .
C9 C8 1.414(8) .
C9 H9 0.9300 .
C12 C11 1.383(9) .
C12 C7 1.396(8) .
C12 H12 0.9300 .
C11 H11 0.9300 .
C4 C3 1.375(8) .
C4 C5 1.389(8) .
C4 C6 1.538(7) .
C7 C8 1.380(8) .
C7 C6 1.548(6) .
C8 H8 0.9300 .
C6 C4 1.538(7) 8_776
C6 C7 1.548(6) 8_776
C5 N1 1.328(8) .
C5 C5 1.499(11) 8_776
C2 C3 1.383(9) .
C2 C1 1.394(10) .
C2 H2 0.9300 .
C1 N1 1.334(9) .
C1 H1 0.9300 .
C3 H3 0.9300 .
