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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/7/24/90/7249016.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_7249016
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 F3 I3, C8 H6 N2 O'
_chemical_formula_sum            'C14 H6 F3 I3 N2 O'
_chemical_formula_weight         655.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 95.150(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9988(3)
_cell_length_b                   17.7100(8)
_cell_length_c                   19.4968(10)
_cell_measurement_reflns_used    6158
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.7520
_cell_measurement_theta_min      4.5870
_cell_volume                     1719.06(16)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16079
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_min         4.291
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.534
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.354
_refine_diff_density_min         -1.798
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0556
_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)+(0.0375P)²+7.3685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3112
_reflns_number_total             3748
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00557k2.cif
_cod_data_source_block           pox_135tfib
_cod_depositor_comments
'Adding full bibliography for 7249013--7249033.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249016
_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'
'x-1/2, -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_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 0.42913(11) 0.43183(3) 0.34683(3) 0.05318(18) Uani 1 1 d . . . . .
I3 I -0.47469(11) 0.45067(3) 0.11862(3) 0.05616(18) Uani 1 1 d . . . . .
I2 I 0.03805(19) 0.73416(4) 0.23749(5) 0.1045(4) Uani 1 1 d . . . . .
F1 F 0.3775(11) 0.6070(3) 0.3201(3) 0.0698(15) Uani 1 1 d . . . . .
F3 F -0.0327(10) 0.3875(3) 0.2306(3) 0.0624(13) Uani 1 1 d . . . . .
F2 F -0.3506(11) 0.6224(3) 0.1525(3) 0.0719(15) Uani 1 1 d . . . . .
O1 O 1.2836(13) 0.1657(4) 0.4572(3) 0.0693(18) Uani 1 1 d . . . . .
N1 N 0.8003(15) 0.3594(4) 0.4500(4) 0.0586(18) Uani 1 1 d . . . . .
C9 C 0.1698(15) 0.4959(4) 0.2791(4) 0.0409(16) Uani 1 1 d . . . . .
C12 C -0.1783(17) 0.5805(4) 0.1935(4) 0.0506(19) Uani 1 1 d . . . . .
C13 C -0.1957(15) 0.5040(4) 0.1894(4) 0.0428(16) Uani 1 1 d . . . . .
N2 N 1.6240(16) 0.1257(5) 0.5273(4) 0.073(2) Uani 1 1 d . . . . .
C2 C 1.1576(15) 0.2854(4) 0.5059(4) 0.0492(19) Uani 1 1 d . . . . .
C6 C 1.3276(14) 0.2191(5) 0.5073(4) 0.0477(19) Uani 1 1 d . . . . .
C1 C 0.9577(17) 0.2982(5) 0.4523(4) 0.054(2) Uani 1 1 d . . . . .
H1 H 0.933304 0.262931 0.416903 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0211(15) 0.4635(4) 0.2333(4) 0.0443(17) Uani 1 1 d . . . . .
C10 C 0.1849(17) 0.5728(4) 0.2785(4) 0.0498(19) Uani 1 1 d . . . . .
C7 C 1.5357(18) 0.1940(6) 0.5488(5) 0.068(3) Uani 1 1 d . . . . .
H7 H 1.610859 0.219704 0.587442 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0081(17) 0.6179(4) 0.2369(4) 0.054(2) Uani 1 1 d . . . . .
C5 C 0.837(2) 0.4077(5) 0.5016(5) 0.071(3) Uani 1 1 d . . . . .
H5 H 0.724496 0.449543 0.501146 0.085 Uiso 1 1 calc R U . . .
C3 C 1.1904(19) 0.3372(6) 0.5583(5) 0.066(3) Uani 1 1 d . . . . .
H3 H 1.319935 0.329702 0.594918 0.079 Uiso 1 1 calc R U . . .
C4 C 1.030(2) 0.4001(6) 0.5560(5) 0.076(3) Uani 1 1 d . . . . .
H4 H 1.051939 0.436669 0.590313 0.092 Uiso 1 1 calc R U . . .
C8 C 1.470(2) 0.1117(6) 0.4732(5) 0.074(3) Uani 1 1 d . . . . .
H8 H 1.483786 0.068155 0.447122 0.089 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 105.2(7) . . ?
C5 N1 C1 117.4(8) . . ?
C10 C9 C14 116.6(7) . . ?
C10 C9 I1 120.9(6) . . ?
C14 C9 I1 122.5(5) . . ?
F2 C12 C13 118.7(7) . . ?
F2 C12 C11 117.6(7) . . ?
C13 C12 C11 123.6(7) . . ?
C12 C13 C14 116.8(7) . . ?
C12 C13 I3 121.6(6) . . ?
C14 C13 I3 121.6(5) . . ?
C8 N2 C7 103.8(8) . . ?
C3 C2 C1 118.6(8) . . ?
C3 C2 C6 119.8(7) . . ?
C1 C2 C6 121.6(8) . . ?
C7 C6 O1 105.6(8) . . ?
C7 C6 C2 134.8(9) . . ?
O1 C6 C2 119.5(6) . . ?
N1 C1 C2 122.3(8) . . ?
F3 C14 C13 118.4(6) . . ?
F3 C14 C9 117.9(7) . . ?
C13 C14 C9 123.6(7) . . ?
F1 C10 C9 118.8(7) . . ?
F1 C10 C11 118.3(7) . . ?
C9 C10 C11 122.9(7) . . ?
C6 C7 N2 111.4(9) . . ?
C12 C11 C10 116.2(7) . . ?
C12 C11 I2 122.0(6) . . ?
C10 C11 I2 121.7(6) . . ?
N1 C5 C4 124.3(9) . . ?
C2 C3 C4 119.3(8) . . ?
C3 C4 C5 118.1(9) . . ?
N2 C8 O1 114.0(9) . . ?
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(7) . ?
I3 C13 2.096(7) . ?
I2 C11 2.065(8) . ?
F1 C10 1.347(9) . ?
F3 C14 1.349(8) . ?
F2 C12 1.344(9) . ?
O1 C8 1.351(11) . ?
O1 C6 1.363(10) . ?
N1 C5 1.320(12) . ?
N1 C1 1.337(11) . ?
C9 C10 1.363(10) . ?
C9 C14 1.372(10) . ?
C12 C13 1.359(11) . ?
C12 C11 1.371(11) . ?
C13 C14 1.370(10) . ?
N2 C8 1.274(12) . ?
N2 C7 1.366(13) . ?
C2 C3 1.372(12) . ?
C2 C1 1.398(10) . ?
C2 C6 1.449(11) . ?
C6 C7 1.336(11) . ?
C10 C11 1.396(11) . ?
C5 C4 1.377(14) . ?
C3 C4 1.369(13) . ?
