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#$Date: 2024-09-06 03:18:20 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/90/7249024.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_7249024
loop_
_publ_author_name
'Sušanj, Ruđer'
'Bedeković, Nikola'
'Cerovski, Sara'
'Baus Topić, Nea'
'Nemec, Vinko'
'Cinčić, Dominik'
_publ_section_title
;
 Evaluation of halogen bonding proclivity of oxazole derivatives carrying
 multiple acceptor sites in cocrystals with perfluorinated iodobenzenes
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              4137
_journal_page_last               4145
_journal_paper_doi               10.1039/D4CE00557K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C6 F4 I2, C8 H6 N2 O'
_chemical_formula_sum            'C14 H6 F4 I2 N2 O'
_chemical_formula_weight         548.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9765(13)
_cell_length_b                   12.8650(13)
_cell_length_c                   13.6805(10)
_cell_measurement_reflns_used    4890
_cell_measurement_temperature    295
_cell_measurement_theta_max      25.0950
_cell_measurement_theta_min      4.3380
_cell_volume                     3163.9(5)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26107
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         4.171
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.692
_refine_diff_density_min         -1.232
_refine_diff_density_rms         0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1097P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.2040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1737
_reflns_number_total             2773
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00557k2.cif
_cod_data_source_block           pox_14tfib
_cod_depositor_comments
'Adding full bibliography for 7249013--7249033.cif.'
_cod_database_code               7249024
_shelx_shelxl_version_number     2019/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.57042(4) 0.81064(8) 0.38395(6) 0.0677(4) Uani 1 1 d . . . . .
I2 I 0.18958(4) 0.92300(7) 0.39079(6) 0.0682(4) Uani 1 1 d . . . . .
F1 F 0.4246(4) 0.6697(6) 0.3836(5) 0.081(2) Uani 1 1 d . . . . .
F4 F 0.4803(4) 1.0269(6) 0.3935(5) 0.080(2) Uani 1 1 d . . . . .
F3 F 0.3355(4) 1.0704(5) 0.4006(5) 0.081(2) Uani 1 1 d . . . . .
F2 F 0.2808(4) 0.7153(6) 0.3870(5) 0.080(2) Uani 1 1 d . . . . .
O1 O 0.5986(5) 0.4412(7) 0.3730(7) 0.090(3) Uani 1 1 d . . . . .
N1 N 0.7788(6) 0.2434(10) 0.3612(8) 0.077(3) Uani 1 1 d . . . . .
C12 C 0.3025(6) 0.8941(11) 0.3932(7) 0.058(3) Uani 1 1 d . . . . .
C9 C 0.4568(6) 0.8477(11) 0.3918(7) 0.060(3) Uani 1 1 d . . . . .
C10 C 0.4040(6) 0.7699(10) 0.3894(7) 0.060(3) Uani 1 1 d . . . . .
N2 N 0.4765(7) 0.4203(10) 0.3811(8) 0.082(3) Uani 1 1 d . . . . .
C14 C 0.4308(6) 0.9487(9) 0.3937(7) 0.055(3) Uani 1 1 d . . . . .
C11 C 0.3290(6) 0.7918(10) 0.3909(7) 0.058(3) Uani 1 1 d . . . . .
C13 C 0.3558(6) 0.9694(9) 0.3967(7) 0.056(3) Uani 1 1 d . . . . .
C6 C 0.5834(7) 0.3356(11) 0.3711(8) 0.061(3) Uani 1 1 d . . . . .
C2 C 0.6471(6) 0.2667(10) 0.3605(8) 0.059(3) Uani 1 1 d . . . . .
C1 C 0.7183(7) 0.3033(10) 0.3716(8) 0.064(3) Uani 1 1 d . . . . .
H1 H 0.724923 0.373090 0.387008 0.076 Uiso 1 1 calc R U . . .
C3 C 0.6356(7) 0.1636(10) 0.3429(9) 0.074(3) Uani 1 1 d . . . . .
H3 H 0.587711 0.136972 0.337806 0.089 Uiso 1 1 calc R U . . .
C5 C 0.7668(8) 0.1442(13) 0.3435(10) 0.085(4) Uani 1 1 d . . . . .
H5 H 0.808175 0.101246 0.337698 0.101 Uiso 1 1 calc R U . . .
C7 C 0.5080(7) 0.3228(12) 0.3747(8) 0.073(4) Uani 1 1 d . . . . .
H7 H 0.482508 0.259930 0.373137 0.088 Uiso 1 1 calc R U . . .
C4 C 0.6975(7) 0.0990(12) 0.3327(10) 0.086(4) Uani 1 1 d . . . . .
H4 H 0.692374 0.028548 0.319277 0.104 Uiso 1 1 calc R U . . .
C8 C 0.5306(9) 0.4857(14) 0.3777(11) 0.103(5) Uani 1 1 d . . . . .
H8 H 0.523579 0.557275 0.378444 0.124 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C8 O1 C6 103.8(11) . . ?
C5 N1 C1 116.3(12) . . ?
C13 C12 C11 115.5(11) . . ?
C13 C12 I2 124.2(10) . . ?
C11 C12 I2 120.3(9) . . ?
C14 C9 C10 116.7(11) . . ?
C14 C9 I1 123.0(9) . . ?
C10 C9 I1 120.2(10) . . ?
F1 C10 C11 117.9(11) . . ?
F1 C10 C9 120.5(10) . . ?
C11 C10 C9 121.6(12) . . ?
C8 N2 C7 106.4(12) . . ?
F4 C14 C13 120.3(11) . . ?
F4 C14 C9 118.7(11) . . ?
C13 C14 C9 121.0(11) . . ?
F2 C11 C10 119.4(12) . . ?
F2 C11 C12 118.8(11) . . ?
C10 C11 C12 121.8(11) . . ?
F3 C13 C12 119.8(10) . . ?
F3 C13 C14 116.9(10) . . ?
C12 C13 C14 123.3(12) . . ?
C7 C6 O1 108.2(11) . . ?
C7 C6 C2 135.4(13) . . ?
O1 C6 C2 116.3(11) . . ?
C3 C2 C1 119.6(12) . . ?
C3 C2 C6 119.4(11) . . ?
C1 C2 C6 120.9(12) . . ?
N1 C1 C2 123.2(12) . . ?
C2 C3 C4 118.4(12) . . ?
N1 C5 C4 125.1(14) . . ?
C6 C7 N2 107.5(12) . . ?
C5 C4 C3 117.2(14) . . ?
N2 C8 O1 114.1(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C9 2.100(11) . ?
I2 C12 2.065(11) . ?
F1 C10 1.344(14) . ?
F4 C14 1.344(12) . ?
F3 C13 1.350(12) . ?
F2 C11 1.313(14) . ?
O1 C8 1.350(19) . ?
O1 C6 1.386(14) . ?
N1 C5 1.317(18) . ?
N1 C1 1.340(15) . ?
C12 C13 1.363(17) . ?
C12 C11 1.399(17) . ?
C9 C14 1.381(17) . ?
C9 C10 1.381(18) . ?
C10 C11 1.376(16) . ?
N2 C8 1.287(19) . ?
N2 C7 1.378(17) . ?
C14 C13 1.375(16) . ?
C6 C7 1.366(17) . ?
C6 C2 1.456(16) . ?
C2 C3 1.363(16) . ?
C2 C1 1.373(16) . ?
C3 C4 1.395(17) . ?
C5 C4 1.383(17) . ?
