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#$Date: 2022-06-03 10:41:30 +0300 (Fri, 03 Jun 2022) $
#$Revision: 275762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105331.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_8105331
loop_
_publ_author_name
'Zhang, Lingfan'
'Ding, Man-Hua'
_publ_section_title
;
 The crystal structure of
 1,8-bis(pyridin-4-ylethynyl)anthracene-1,2,4,5-tetrafluoro-3,6-diiodobenzene
 (2/1), C62H32F4I2N4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              919
_journal_page_last               921
_journal_paper_doi               10.1515/ncrs-2020-0102
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C31 H16 F2 I N2'
_chemical_formula_weight         581.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                106.740(9)
_cell_angle_beta                 98.981(9)
_cell_angle_gamma                115.198(9)
_cell_formula_units_Z            2
_cell_length_a                   10.201(9)
_cell_length_b                   10.897(9)
_cell_length_c                   13.499(12)
_cell_measurement_reflns_used    7433
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.20
_cell_volume                     1231.1(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11786
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.664
_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       prism
_exptl_crystal_F_000             574
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.230
_exptl_transmission_factor_max   0.75
_exptl_transmission_factor_min   0.60
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0274P)²+0.4209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0673
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3920
_reflns_number_total             4317
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0102_suppl.cif
_cod_data_source_block           1907311_0m_a
_cod_original_cell_volume        1231.1(18)
_cod_database_code               8105331
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.603
_shelx_estimated_absorpt_t_max   0.748
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.16536(2) 0.83169(2) 0.77971(2) 0.06046(8) Uani 1 1 d . . . . .
F1 F 0.36054(18) 1.15645(16) 0.97117(13) 0.0677(4) Uani 1 1 d . . . . .
F2 F 0.38611(18) 0.71614(15) 0.86054(12) 0.0659(4) Uani 1 1 d . . . . .
N1 N 0.8650(3) 0.6543(3) 0.6110(2) 0.0788(7) Uani 1 1 d . . . . .
N2 N 1.0337(4) 0.3256(4) 0.7559(3) 0.1050(11) Uani 1 1 d . . . . .
C1 C 0.7440(4) 0.5694(3) 0.6318(2) 0.0750(8) Uani 1 1 d . . . . .
H1 H 0.7423 0.5987 0.7032 0.090 Uiso 1 1 calc R U . . .
C2 C 0.6205(3) 0.4406(3) 0.5545(2) 0.0696(7) Uani 1 1 d . . . . .
H2 H 0.5379 0.3854 0.5736 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6209(3) 0.3942(3) 0.4478(2) 0.0536(6) Uani 1 1 d . . . . .
C4 C 0.7459(3) 0.4819(3) 0.4249(2) 0.0749(8) Uani 1 1 d . . . . .
H4 H 0.7511 0.4556 0.3543 0.090 Uiso 1 1 calc R U . . .
C5 C 0.8639(4) 0.6101(4) 0.5089(3) 0.0914(11) Uani 1 1 d . . . . .
H5 H 0.9476 0.6687 0.4924 0.110 Uiso 1 1 calc R U . . .
C6 C 0.4948(3) 0.2604(3) 0.3640(2) 0.0598(6) Uani 1 1 d . . . . .
C7 C 0.3914(3) 0.1505(3) 0.2926(2) 0.0554(6) Uani 1 1 d . . . . .
C8 C 0.2738(3) 0.0166(2) 0.2027(2) 0.0518(5) Uani 1 1 d . . . . .
C9 C 0.1474(3) 0.0114(3) 0.1459(2) 0.0653(7) Uani 1 1 d . . . . .
H9 H 0.1341 0.0932 0.1677 0.078 Uiso 1 1 calc R U . . .
C10 C 0.0364(3) -0.1176(3) 0.0540(2) 0.0701(8) Uani 1 1 d . . . . .
H10 H -0.0513 -0.1212 0.0176 0.084 Uiso 1 1 calc R U . . .
C11 C 0.0561(3) -0.2359(3) 0.0184(2) 0.0632(7) Uani 1 1 d . . . . .
H11 H -0.0159 -0.3175 -0.0445 0.076 Uiso 1 1 calc R U . . .
C12 C 0.1846(3) -0.2384(2) 0.07492(19) 0.0507(5) Uani 1 1 d . . . . .
C13 C 0.2057(3) -0.3595(3) 0.0415(2) 0.0571(6) Uani 1 1 d . . . . .
H13 H 0.1379 -0.4396 -0.0234 0.069 Uiso 1 1 calc R U . . .
C14 C 0.3251(3) -0.3648(3) 0.1021(2) 0.0555(6) Uani 1 1 d . . . . .
C15 C 0.4293(3) -0.2408(2) 0.20265(19) 0.0484(5) Uani 1 1 d . . . . .
C16 C 0.4128(3) -0.1160(2) 0.23321(18) 0.0468(5) Uani 1 1 d . . . . .
H16 H 0.4833 -0.0340 0.2964 0.056 Uiso 1 1 calc R U . . .
C17 C 0.2941(3) -0.1105(2) 0.17208(18) 0.0464(5) Uani 1 1 d . . . . .
C18 C 0.3466(4) -0.4897(3) 0.0697(3) 0.0739(8) Uani 1 1 d . . . . .
H18 H 0.2817 -0.5692 0.0037 0.089 Uiso 1 1 calc R U . . .
C19 C 0.4581(4) -0.4950(3) 0.1322(3) 0.0844(9) Uani 1 1 d . . . . .
H19 H 0.4698 -0.5777 0.1090 0.101 Uiso 1 1 calc R U . . .
C20 C 0.5579(4) -0.3766(3) 0.2327(3) 0.0758(8) Uani 1 1 d . . . . .
H20 H 0.6332 -0.3833 0.2759 0.091 Uiso 1 1 calc R U . . .
C21 C 0.5459(3) -0.2515(3) 0.2681(2) 0.0576(6) Uani 1 1 d . . . . .
C22 C 0.6467(3) -0.1326(3) 0.3715(2) 0.0593(6) Uani 1 1 d . . . . .
C23 C 0.7273(3) -0.0343(3) 0.4583(2) 0.0637(7) Uani 1 1 d . . . . .
C24 C 0.8289(3) 0.0867(3) 0.5603(2) 0.0640(7) Uani 1 1 d . . . . .
C25 C 0.8165(4) 0.2129(4) 0.5962(3) 0.0823(9) Uani 1 1 d . . . . .
H25 H 0.7398 0.2205 0.5557 0.099 Uiso 1 1 calc R U . . .
C26 C 0.9222(6) 0.3279(4) 0.6946(3) 0.1035(13) Uani 1 1 d . . . . .
H26 H 0.9131 0.4120 0.7184 0.124 Uiso 1 1 calc R U . . .
C27 C 1.0416(4) 0.2026(5) 0.7217(3) 0.0967(12) Uani 1 1 d . . . . .
H27 H 1.1178 0.1976 0.7651 0.116 Uiso 1 1 calc R U . . .
C28 C 0.9439(3) 0.0821(4) 0.6259(3) 0.0774(8) Uani 1 1 d . . . . .
H28 H 0.9551 -0.0011 0.6056 0.093 Uiso 1 1 calc R U . . .
C29 C 0.3666(3) 0.9329(2) 0.91049(18) 0.0473(5) Uani 1 1 d . . . . .
C30 C 0.4283(3) 1.0770(2) 0.9843(2) 0.0489(5) Uani 1 1 d . . . . .
C31 C 0.4411(3) 0.8580(2) 0.92884(19) 0.0479(5) 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 0.0033 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 N1 C1 116.5(3) . .
C26 N2 C27 116.6(4) . .
N1 C1 C2 124.1(3) . .
N1 C1 H1 117.9 . .
C2 C1 H1 117.9 . .
C1 C2 C3 119.0(3) . .
C1 C2 H2 120.5 . .
C3 C2 H2 120.5 . .
C4 C3 C2 117.5(2) . .
C4 C3 C6 121.3(3) . .
C2 C3 C6 121.2(3) . .
C3 C4 C5 118.8(3) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
N1 C5 C4 124.1(3) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
C7 C6 C3 178.4(3) . .
C6 C7 C8 176.1(3) . .
C9 C8 C17 120.5(2) . .
C9 C8 C7 120.7(2) . .
C17 C8 C7 118.8(2) . .
C8 C9 C10 120.4(3) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C11 C10 C9 120.8(3) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C10 C11 C12 121.6(2) . .
C10 C11 H11 119.2 . .
C12 C11 H11 119.2 . .
C13 C12 C11 122.7(2) . .
C13 C12 C17 119.3(2) . .
C11 C12 C17 118.0(2) . .
C12 C13 C14 122.0(2) . .
C12 C13 H13 119.0 . .
C14 C13 H13 119.0 . .
C13 C14 C18 122.6(2) . .
C13 C14 C15 118.8(2) . .
C18 C14 C15 118.6(3) . .
C16 C15 C21 122.6(2) . .
C16 C15 C14 119.1(2) . .
C21 C15 C14 118.3(2) . .
C17 C16 C15 121.9(2) . .
C17 C16 H16 119.1 . .
C15 C16 H16 119.1 . .
C16 C17 C12 118.7(2) . .
C16 C17 C8 122.9(2) . .
C12 C17 C8 118.4(2) . .
C19 C18 C14 121.4(3) . .
C19 C18 H18 119.3 . .
C14 C18 H18 119.3 . .
C18 C19 C20 120.7(3) . .
C18 C19 H19 119.7 . .
C20 C19 H19 119.7 . .
C21 C20 C19 121.1(3) . .
C21 C20 H20 119.5 . .
C19 C20 H20 119.5 . .
C20 C21 C22 120.5(3) . .
C20 C21 C15 119.9(3) . .
C22 C21 C15 119.6(2) . .
C23 C22 C21 178.3(3) . .
C22 C23 C24 177.5(3) . .
C28 C24 C25 117.7(3) . .
C28 C24 C23 121.0(3) . .
C25 C24 C23 121.3(3) . .
C24 C25 C26 118.1(4) . .
C24 C25 H25 120.9 . .
C26 C25 H25 121.0 . .
N2 C26 C25 124.5(4) . .
N2 C26 H26 117.8 . .
C25 C26 H26 117.8 . .
N2 C27 C28 124.1(4) . .
N2 C27 H27 118.0 . .
C28 C27 H27 118.0 . .
C27 C28 C24 119.0(4) . .
C27 C28 H28 120.5 . .
C24 C28 H28 120.5 . .
C31 C29 C30 117.1(2) . .
C31 C29 I1 121.50(17) . .
C30 C29 I1 121.39(17) . .
F1 C30 C31 118.8(2) . 2_677
F1 C30 C29 120.1(2) . .
C31 C30 C29 121.1(2) 2_677 .
F2 C31 C30 118.0(2) . 2_677
F2 C31 C29 120.2(2) . .
C30 C31 C29 121.8(2) 2_677 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C29 2.090(3) .
F1 C30 1.348(3) .
F2 C31 1.354(3) .
N1 C5 1.318(4) .
N1 C1 1.320(4) .
N2 C26 1.312(6) .
N2 C27 1.328(6) .
C1 C2 1.373(4) .
C1 H1 0.9300 .
C2 C3 1.384(4) .
C2 H2 0.9300 .
C3 C4 1.375(4) .
C3 C6 1.435(3) .
C4 C5 1.384(4) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C7 1.191(3) .
C7 C8 1.441(3) .
C8 C9 1.363(4) .
C8 C17 1.441(4) .
C9 C10 1.414(4) .
C9 H9 0.9300 .
C10 C11 1.351(4) .
C10 H10 0.9300 .
C11 C12 1.425(4) .
C11 H11 0.9300 .
C12 C13 1.385(4) .
C12 C17 1.440(3) .
C13 C14 1.390(4) .
C13 H13 0.9300 .
C14 C18 1.426(4) .
C14 C15 1.438(3) .
C15 C16 1.393(3) .
C15 C21 1.435(4) .
C16 C17 1.389(3) .
C16 H16 0.9300 .
C18 C19 1.340(5) .
C18 H18 0.9300 .
C19 C20 1.408(5) .
C19 H19 0.9300 .
C20 C21 1.374(4) .
C20 H20 0.9300 .
C21 C22 1.435(4) .
C22 C23 1.193(4) .
C23 C24 1.433(4) .
C24 C28 1.384(4) .
C24 C25 1.388(5) .
C25 C26 1.393(5) .
C25 H25 0.9300 .
C26 H26 0.9300 .
C27 C28 1.376(5) .
C27 H27 0.9300 .
C28 H28 0.9300 .
C29 C31 1.375(3) .
C29 C30 1.384(3) .
C30 C31 1.372(3) 2_677
C31 C30 1.372(3) 2_677
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 0.2(5) . . . .
N1 C1 C2 C3 0.5(5) . . . .
C1 C2 C3 C4 -0.7(4) . . . .
C1 C2 C3 C6 179.9(3) . . . .
C2 C3 C4 C5 0.4(5) . . . .
C6 C3 C4 C5 179.7(3) . . . .
C1 N1 C5 C4 -0.6(6) . . . .
C3 C4 C5 N1 0.3(6) . . . .
C17 C8 C9 C10 -1.8(4) . . . .
C7 C8 C9 C10 176.4(3) . . . .
C8 C9 C10 C11 -2.5(4) . . . .
C9 C10 C11 C12 3.3(4) . . . .
C10 C11 C12 C13 178.5(3) . . . .
C10 C11 C12 C17 0.1(4) . . . .
C11 C12 C13 C14 -174.9(2) . . . .
C17 C12 C13 C14 3.5(4) . . . .
C12 C13 C14 C18 178.8(2) . . . .
C12 C13 C14 C15 0.2(4) . . . .
C13 C14 C15 C16 -3.6(3) . . . .
C18 C14 C15 C16 177.7(2) . . . .
C13 C14 C15 C21 175.9(2) . . . .
C18 C14 C15 C21 -2.8(3) . . . .
C21 C15 C16 C17 -176.3(2) . . . .
C14 C15 C16 C17 3.2(3) . . . .
C15 C16 C17 C12 0.6(3) . . . .
C15 C16 C17 C8 179.3(2) . . . .
C13 C12 C17 C16 -3.9(3) . . . .
C11 C12 C17 C16 174.6(2) . . . .
C13 C12 C17 C8 177.3(2) . . . .
C11 C12 C17 C8 -4.2(3) . . . .
C9 C8 C17 C16 -173.6(2) . . . .
C7 C8 C17 C16 8.1(3) . . . .
C9 C8 C17 C12 5.1(3) . . . .
C7 C8 C17 C12 -173.2(2) . . . .
C13 C14 C18 C19 -176.7(3) . . . .
C15 C14 C18 C19 1.9(4) . . . .
C14 C18 C19 C20 0.2(5) . . . .
C18 C19 C20 C21 -1.5(5) . . . .
C19 C20 C21 C22 179.0(3) . . . .
C19 C20 C21 C15 0.6(4) . . . .
C16 C15 C21 C20 -179.0(2) . . . .
C14 C15 C21 C20 1.6(4) . . . .
C16 C15 C21 C22 2.6(4) . . . .
C14 C15 C21 C22 -176.9(2) . . . .
C28 C24 C25 C26 1.3(5) . . . .
C23 C24 C25 C26 -178.0(3) . . . .
C27 N2 C26 C25 -1.9(6) . . . .
C24 C25 C26 N2 0.3(6) . . . .
C26 N2 C27 C28 2.0(6) . . . .
N2 C27 C28 C24 -0.5(5) . . . .
C25 C24 C28 C27 -1.2(4) . . . .
C23 C24 C28 C27 178.1(3) . . . .
C31 C29 C30 F1 -179.8(2) . . . .
I1 C29 C30 F1 -1.7(3) . . . .
C31 C29 C30 C31 0.7(4) . . . 2_677
I1 C29 C30 C31 178.81(18) . . . 2_677
C30 C29 C31 F2 179.2(2) . . . .
I1 C29 C31 F2 1.1(3) . . . .
C30 C29 C31 C30 -0.7(4) . . . 2_677
I1 C29 C31 C30 -178.81(18) . . . 2_677
