#------------------------------------------------------------------------------
#$Date: 2020-04-06 01:10:09 +0300 (Mon, 06 Apr 2020) $
#$Revision: 250390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243342.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_2243342
loop_
_publ_author_name
'Cui, Yu-Jin'
'Su, Feng'
'Jin, Wei-Jun'
_publ_section_title
;
 Structural and luminescent properties of co-crystals of tetraiodoethylene
 with two azaphenanthrenes
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              438
_journal_page_last               442
_journal_paper_doi               10.1107/S2056989020002182
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '0.5C2 I4 , C13 H9 N'
_chemical_formula_moiety         '0.5 (C2 I4) , (C13 H9 N)'
_chemical_formula_sum            'C14 H9 I2 N'
_chemical_formula_weight         445.02
_chemical_name_systematic
;
Tetraiodoethylene--benzo[f]quinoline (1/2)
;
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                97.050(2)
_cell_angle_beta                 92.059(2)
_cell_angle_gamma                95.579(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3179(4)
_cell_length_b                   8.1089(5)
_cell_length_c                   11.3252(7)
_cell_measurement_reflns_used    4699
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.80
_cell_volume                     663.02(7)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008),
DIAMOND (Brandenburg, 2005),
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8567
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.720
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.229
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.738
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0276
_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)+(0.0189P)²+0.7413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                2099
_reflns_number_total             2701
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2225sup1.cif
_cod_data_source_block           2
_cod_database_code               2243342
_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   0.289
_shelx_estimated_absorpt_t_max   0.332
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.20988(4) 0.45307(3) 0.82595(2) 0.04767(10) Uani d 1 . .
I I2 -0.08934(4) 0.75374(3) 0.91391(3) 0.05167(11) Uani d 1 . .
N N1 0.4565(5) 0.3596(5) 0.6400(3) 0.0518(9) Uani d 1 . .
C C1 0.6267(7) 0.4270(6) 0.6615(4) 0.0597(13) Uani d 1 . .
H H1 0.655445 0.495377 0.733212 0.072 Uiso calc 1 . .
C C2 0.7655(7) 0.4022(6) 0.5841(5) 0.0613(13) Uani d 1 . .
H H2 0.883874 0.453358 0.603495 0.074 Uiso calc 1 . .
C C3 0.7274(6) 0.3026(6) 0.4794(5) 0.0541(12) Uani d 1 . .
H H3 0.819507 0.286190 0.425958 0.065 Uiso calc 1 . .
C C4 0.5492(5) 0.2240(5) 0.4514(4) 0.0399(10) Uani d 1 . .
C C5 0.4171(5) 0.2587(5) 0.5350(4) 0.0389(9) Uani d 1 . .
C C6 0.2327(6) 0.1869(5) 0.5119(4) 0.0470(11) Uani d 1 . .
H H6 0.144788 0.211154 0.566982 0.056 Uiso calc 1 . .
C C7 0.1844(6) 0.0845(5) 0.4114(4) 0.0471(11) Uani d 1 . .
H H7 0.062732 0.038787 0.398340 0.057 Uiso calc 1 . .
C C8 0.3128(6) 0.0431(5) 0.3238(4) 0.0424(10) Uani d 1 . .
C C9 0.4960(6) 0.1144(5) 0.3424(4) 0.0418(10) Uani d 1 . .
C C10 0.6199(7) 0.0731(6) 0.2544(4) 0.0561(12) Uani d 1 . .
H H10 0.741510 0.119847 0.264207 0.067 Uiso calc 1 . .
C C11 0.5643(9) -0.0348(7) 0.1546(5) 0.0730(16) Uani d 1 . .
H H11 0.648615 -0.060734 0.097457 0.088 Uiso calc 1 . .
C C12 0.3842(9) -0.1063(7) 0.1373(4) 0.0716(16) Uani d 1 . .
H H12 0.347907 -0.180218 0.069304 0.086 Uiso calc 1 . .
C C13 0.2612(7) -0.0676(6) 0.2203(4) 0.0555(12) Uani d 1 . .
H H13 0.140145 -0.115380 0.208420 0.067 Uiso calc 1 . .
C C14 0.0238(6) 0.5360(5) 0.9536(4) 0.0449(10) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 . . 117.4(4) ?
N1 C1 C2 . . 123.8(5) ?
N1 C1 H1 . . 118.1 ?
C2 C1 H1 . . 118.1 ?
C3 C2 C1 . . 119.2(4) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 120.1(4) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 116.5(4) ?
C3 C4 C9 . . 124.0(4) ?
C5 C4 C9 . . 119.5(4) ?
N1 C5 C4 . . 123.0(4) ?
N1 C5 C6 . . 117.1(4) ?
C4 C5 C6 . . 119.9(4) ?
C7 C6 C5 . . 120.4(4) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 122.3(4) ?
C6 C7 H7 . . 118.9 ?
C8 C7 H7 . . 118.9 ?
C13 C8 C9 . . 119.4(4) ?
C13 C8 C7 . . 121.7(4) ?
C9 C8 C7 . . 118.9(4) ?
C10 C9 C8 . . 118.0(4) ?
C10 C9 C4 . . 123.0(4) ?
C8 C9 C4 . . 119.0(4) ?
C11 C10 C9 . . 120.9(5) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 121.0(5) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C13 C12 C11 . . 119.5(5) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C8 . . 121.3(5) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C14 C14 I2 2_567 . 121.4(4) ?
C14 C14 I1 2_567 . 126.2(4) ?
I2 C14 I1 . . 112.33(18) ?
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 C14 . 2.116(4) ?
I2 C14 . 2.111(4) ?
N1 C1 . 1.313(6) ?
N1 C5 . 1.363(5) ?
C1 C2 . 1.379(7) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.354(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.402(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.401(5) ?
C4 C9 . 1.448(6) ?
C5 C6 . 1.418(6) ?
C6 C7 . 1.339(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.423(6) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.402(6) ?
C8 C9 . 1.405(6) ?
C9 C10 . 1.403(6) ?
C10 C11 . 1.365(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(8) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.355(7) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C14 2_567 1.305(8) ?
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
C1 H1 I2 1_655 0.93 3.16 4.019(5) 155
C6 H6 I1 . 0.93 3.31 3.945(4) 127
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
C5 N1 C1 C2 . . . . 0.5(7) ?
N1 C1 C2 C3 . . . . -0.3(8) ?
C1 C2 C3 C4 . . . . -0.9(7) ?
C2 C3 C4 C5 . . . . 1.7(6) ?
C2 C3 C4 C9 . . . . -179.4(4) ?
C1 N1 C5 C4 . . . . 0.5(6) ?
C1 N1 C5 C6 . . . . -179.7(4) ?
C3 C4 C5 N1 . . . . -1.6(6) ?
C9 C4 C5 N1 . . . . 179.5(4) ?
C3 C4 C5 C6 . . . . 178.6(4) ?
C9 C4 C5 C6 . . . . -0.3(6) ?
N1 C5 C6 C7 . . . . -179.0(4) ?
C4 C5 C6 C7 . . . . 0.8(6) ?
C5 C6 C7 C8 . . . . -0.1(7) ?
C6 C7 C8 C13 . . . . 178.4(4) ?
C6 C7 C8 C9 . . . . -1.1(6) ?
C13 C8 C9 C10 . . . . 1.1(6) ?
C7 C8 C9 C10 . . . . -179.4(4) ?
C13 C8 C9 C4 . . . . -177.9(4) ?
C7 C8 C9 C4 . . . . 1.6(6) ?
C3 C4 C9 C10 . . . . 1.3(6) ?
C5 C4 C9 C10 . . . . -179.8(4) ?
C3 C4 C9 C8 . . . . -179.7(4) ?
C5 C4 C9 C8 . . . . -0.9(6) ?
C8 C9 C10 C11 . . . . -0.9(6) ?
C4 C9 C10 C11 . . . . 178.1(4) ?
C9 C10 C11 C12 . . . . 0.1(8) ?
C10 C11 C12 C13 . . . . 0.4(8) ?
C11 C12 C13 C8 . . . . -0.2(7) ?
C9 C8 C13 C12 . . . . -0.5(6) ?
C7 C8 C13 C12 . . . . 180.0(4) ?

_cod_database_fobs_code 2243342
