#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058311.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_7058311
loop_
_publ_author_name
'Torubaev, Yury V.'
'Rai, Dhirendra K.'
'Skabitsky, Ivan V.'
'Pakhira, Srimanta'
'Dmitrienko, Artem'
_publ_section_title
;
 Energy framework approach to the supramolecular reactions: interplay of
 the secondary bonding interaction in Ph2E2 (E = Se, Te)/p-I-C6F4-I
 co-crystals
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7941
_journal_paper_doi               10.1039/C9NJ00347A
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C3 F2 I, C12 H10 Se2'
_chemical_formula_sum            'C15 H10 F2 I Se2'
_chemical_formula_weight         513.07
_chemical_name_systematic
'diphenyl diseleride 1,2,4,5-tetrafluoro-3,6-diiodobenzene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2018-01-10 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.613(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1178(7)
_cell_length_b                   5.6743(4)
_cell_length_c                   26.6419(18)
_cell_measurement_reflns_used    5010
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.44
_cell_volume                     1524.59(18)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15346
_diffrn_reflns_theta_full        28.3654
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.882
_exptl_absorpt_correction_T_max  0.8257
_exptl_absorpt_correction_T_min  0.2606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.3156.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.2351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             954.2637
_exptl_crystal_size_max          0.668
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.6900
_refine_diff_density_min         -0.5801
_refine_diff_density_rms         0.1476
_refine_ls_d_res_high            0.7480
_refine_ls_d_res_low             8.3615
_refine_ls_goodness_of_fit_ref   1.0103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0103
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0229
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0221P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0461
_refine_ls_wR_factor_ref         0.0484
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                3214
_reflns_number_total             3816
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9nj00347a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7058311--7058312.cif.'
_cod_database_code               7058311
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C4(H4), C10(H10), C12(H12), C8(H8), C9(H9), C5(H5), C3(H3),
 C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,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_refinement_flags_posn
I1 I -0.777767(4) 0.120938(4) 0.565931(4) 0.02777(5) Uani 1.000000 .
Se2 Se -0.292035(4) 0.544498(4) 0.282702(4) 0.02357(6) Uani 1.000000 .
Se1 Se -0.372922(4) 0.163273(4) 0.283316(4) 0.02276(6) Uani 1.000000 .
F1 F -1.093883(4) 0.157650(4) 0.558587(4) 0.0344(3) Uani 1.000000 .
F4 F -0.736419(4) 0.550906(4) 0.490771(4) 0.0357(3) Uani 1.000000 .
C4 C -0.587747(4) 0.104113(4) 0.433169(4) 0.0308(4) Uani 1.000000 .
C5 C -0.602957(4) -0.066196(4) 0.395855(4) 0.0296(5) Uani 1.000000 .
C10 C 0.157332(4) 0.465539(4) 0.340440(4) 0.0336(5) Uani 1.000000 .
C3 C -0.507410(4) 0.297374(4) 0.426386(4) 0.0309(4) Uani 1.000000 .
C7 C -0.109278(4) 0.502553(4) 0.308378(4) 0.0198(4) Uani 1.000000 .
C11 C 0.068883(4) 0.292339(4) 0.352190(4) 0.0359(5) Uani 1.000000 .
C1 C -0.458380(4) 0.149918(4) 0.345627(4) 0.0204(4) Uani 1.000000 .
C13 C -0.910352(4) 0.346073(4) 0.526454(4) 0.0216(4) Uani 1.000000 .
C8 C -0.022699(4) 0.679278(4) 0.296671(4) 0.0257(4) Uani 1.000000 .
C12 C -0.063716(4) 0.309525(4) 0.336259(4) 0.0315(5) Uani 1.000000 .
C18 C -0.866672(4) 0.522286(4) 0.495858(4) 0.0233(4) Uani 1.000000 .
C6 C -0.539054(4) -0.044268(4) 0.352044(4) 0.0243(4) Uani 1.000000 .
C2 C -0.441823(4) 0.320194(4) 0.382685(4) 0.0259(4) Uani 1.000000 .
C9 C 0.111044(4) 0.659319(4) 0.313310(4) 0.0317(5) Uani 1.000000 .
C14 C -1.044833(4) 0.326792(4) 0.529954(4) 0.0227(4) Uani 1.000000 .
H2 H -0.387176(4) 0.449268(4) 0.378448(4) 0.0311(5) Uiso 1.000000 R
H4 H -0.631070(4) 0.088797(4) 0.462488(4) 0.0370(5) Uiso 1.000000 R
H8 H -0.053266(4) 0.809492(4) 0.277975(4) 0.0308(5) Uiso 1.000000 R
H5 H -0.656593(4) -0.196436(4) 0.400286(4) 0.0355(6) Uiso 1.000000 R
H3 H -0.497240(4) 0.412656(4) 0.451209(4) 0.0370(5) Uiso 1.000000 R
H9 H 0.169710(4) 0.778328(4) 0.305998(4) 0.0380(6) Uiso 1.000000 R
H12 H -0.122341(4) 0.191630(4) 0.344242(4) 0.0378(6) Uiso 1.000000 R
H10 H 0.247013(4) 0.451403(4) 0.350729(4) 0.0404(6) Uiso 1.000000 R
H6 H -0.550040(4) -0.158729(4) 0.327073(4) 0.0292(5) Uiso 1.000000 R
H11 H 0.099244(4) 0.162589(4) 0.371083(4) 0.0431(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C7 Se2 Se1 102.189(2) .
C1 Se1 Se2 103.036(4) .
C3 C4 C5 119.390(9) .
H4 C4 C5 120.305(4) .
H4 C4 C3 120.305(6) .
C6 C5 C4 120.630(4) .
H5 C5 C4 119.685(4) .
H5 C5 C6 119.685(2) .
C9 C10 C11 119.186(4) .
H10 C10 C11 120.407(3) .
H10 C10 C9 120.407(2) .
C2 C3 C4 120.462(7) .
H3 C3 C4 119.769(6) .
H3 C3 C2 119.769(3) .
C8 C7 Se2 115.833(5) .
C12 C7 Se2 123.773(3) .
C12 C7 C8 120.389(5) .
C12 C11 C10 120.810(6) .
H11 C11 C10 119.595(3) .
H11 C11 C12 119.595(3) .
C6 C1 Se1 116.370(7) .
C2 C1 Se1 123.298(4) .
C2 C1 C6 120.331(9) .
C18 C13 I1 121.244(4) .
C14 C13 I1 121.266(6) .
C14 C13 C18 117.488(5) .
C9 C8 C7 119.036(5) .
H8 C8 C7 120.482(3) .
H8 C8 C9 120.482(3) .
C11 C12 C7 119.756(4) .
H12 C12 C7 120.122(2) .
H12 C12 C11 120.122(3) .
C13 C18 F4 120.532(5) .
C14 C18 F4 118.415(7) 3_366
C14 C18 C13 121.053(5) 3_366
C1 C6 C5 119.575(7) .
H6 C6 C5 120.212(3) .
H6 C6 C1 120.212(6) .
C1 C2 C3 119.608(4) .
H2 C2 C3 120.196(3) .
H2 C2 C1 120.196(4) .
C8 C9 C10 120.807(4) .
H9 C9 C10 119.597(2) .
H9 C9 C8 119.597(3) .
C13 C14 F1 120.471(5) .
C18 C14 F1 118.068(5) 3_366
C18 C14 C13 121.459(7) 3_366
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C13 2.07622(12) .
Se2 Se1 2.31335(15) .
Se2 C7 1.93399(14) .
Se1 C1 1.93392(17) .
F1 C14 1.34545(12) .
F4 C18 1.34546(11) .
C4 C5 1.38609(13) .
C4 C3 1.38548(9) .
C4 H4 0.9300 .
C5 C6 1.38465(16) .
C5 H5 0.9300 .
C10 C11 1.38195(9) .
C10 C9 1.37708(11) .
C10 H10 0.9300 .
C3 C2 1.39173(16) .
C3 H3 0.9300 .
C7 C8 1.38353(9) .
C7 C12 1.38162(11) .
C11 C12 1.37767(11) .
C11 H11 0.9300 .
C1 C6 1.38998(9) .
C1 C2 1.38195(13) .
C13 C18 1.38474(12) .
C13 C14 1.37566(11) .
C8 C9 1.39426(11) .
C8 H8 0.9300 .
C12 H12 0.9300 .
C18 C14 1.38165(10) 3_366
C6 H6 0.9300 .
C2 H2 0.9300 .
C9 H9 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179229
