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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/7/24/90/7249025.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_7249025
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         'C9 H6 N2 O3, C6 F3 I3'
_chemical_formula_sum            'C15 H6 F3 I3 N2 O3'
_chemical_formula_weight         699.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.092(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9443(2)
_cell_length_b                   17.6264(6)
_cell_length_c                   21.8090(9)
_cell_measurement_reflns_used    13323
_cell_measurement_temperature    298.14(10)
_cell_measurement_theta_max      37.5160
_cell_measurement_theta_min      2.9670
_cell_volume                     1889.93(13)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.14(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8160
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.311
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13457
_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    2.460
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0302
_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)+(0.0192P)²+10.0424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.774
_reflns_Friedel_fraction_max     0.744
_reflns_number_gt                3299
_reflns_number_total             3592
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00557k2.cif
_cod_data_source_block           nox_135tfib
_cod_depositor_comments
'Adding full bibliography for 7249013--7249033.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7249025
_shelx_shelxl_version_number     2018/3
_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, -y, z+1/2'
'x+1/2, y+1/2, 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 0.88328(7) 0.25642(5) 0.51777(3) 0.0482(2) Uani 1 1 d . . . . .
I2 I 1.81087(8) 0.25732(5) 0.71827(3) 0.0526(3) Uani 1 1 d . . . . .
I3 I 1.3618(6) -0.04119(3) 0.61614(15) 0.1045(4) Uani 1 1 d . . . . .
F1 F 1.348(2) 0.3083(2) 0.6171(6) 0.0554(11) Uani 1 1 d . . . . .
F2 F 1.7174(19) 0.0790(6) 0.6956(5) 0.071(3) Uani 1 1 d . . . . .
C12 C 1.536(2) 0.1965(6) 0.6596(6) 0.036(3) Uani 1 1 d . . . . .
F3 F 0.992(2) 0.0797(5) 0.5397(5) 0.067(3) Uani 1 1 d . . . . .
C6 C -0.203(3) 0.4716(8) 0.3261(8) 0.059(4) Uani 1 1 d . . . . .
H6 H -0.178058 0.429508 0.301665 0.071 Uiso 1 1 calc R U . . .
C15 C 1.163(3) 0.1184(9) 0.5779(8) 0.051(4) Uani 1 1 d . . . . .
C9 C 0.398(4) 0.3233(11) 0.3877(10) 0.082(5) Uani 1 1 d . . . . .
H9 H 0.463324 0.279252 0.370899 0.098 Uiso 1 1 calc R U . . .
C11 C 1.341(4) 0.2325(4) 0.6152(10) 0.0388(17) Uani 1 1 d . . . . .
C14 C 1.356(4) 0.0765(4) 0.6176(10) 0.053(2) Uani 1 1 d . . . . .
C4 C -0.438(3) 0.5851(10) 0.3415(9) 0.061(4) Uani 1 1 d . . . . .
C7 C 0.156(2) 0.4224(8) 0.3982(6) 0.040(3) Uani 1 1 d . . . . .
N2 N 0.496(3) 0.3511(10) 0.4413(7) 0.070(4) Uani 1 1 d . . . . .
O1 O -0.799(3) 0.6321(10) 0.2799(8) 0.111(6) Uani 1 1 d . . . . .
C13 C 1.530(3) 0.1164(8) 0.6567(7) 0.045(3) Uani 1 1 d . . . . .
O3 O 0.1940(18) 0.3652(5) 0.3596(4) 0.076(3) Uani 1 1 d . . . . .
C10 C 1.161(3) 0.1941(8) 0.5774(7) 0.044(3) Uani 1 1 d . . . . .
C1 C -0.0462(18) 0.4804(5) 0.3801(5) 0.044(2) Uani 1 1 d . . . . .
C5 C -0.407(2) 0.5256(6) 0.3061(6) 0.061(3) Uani 1 1 d . . . . .
H5 H -0.514879 0.519314 0.268896 0.073 Uiso 1 1 calc R U . . .
C2 C -0.072(3) 0.5433(8) 0.4162(7) 0.048(3) Uani 1 1 d . . . . .
H2 H 0.042685 0.549877 0.452496 0.057 Uiso 1 1 calc R U . . .
C3 C -0.271(2) 0.5976(6) 0.3979(5) 0.060(3) Uani 1 1 d . . . . .
H3 H -0.293336 0.640394 0.421731 0.072 Uiso 1 1 calc R U . . .
N1 N -0.648(2) 0.6422(6) 0.3233(6) 0.072(3) Uani 1 1 d . . . . .
C8 C 0.347(2) 0.4132(7) 0.4491(5) 0.061(3) Uani 1 1 d . . . . .
H8 H 0.367371 0.445012 0.483246 0.073 Uiso 1 1 calc R U . . .
O2 O -0.650(3) 0.6994(8) 0.3517(8) 0.102(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'
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
C13 C12 C11 113.5(11) . . ?
C13 C12 I2 123.9(10) . . ?
C11 C12 I2 122.6(8) . . ?
C1 C6 C5 121.0(13) . . ?
F3 C15 C10 120.6(14) . . ?
F3 C15 C14 117.5(14) . . ?
C10 C15 C14 121.9(14) . . ?
N2 C9 O3 112.8(17) . . ?
C10 C11 F1 122.7(16) . . ?
C10 C11 C12 123.3(6) . . ?
F1 C11 C12 113.9(15) . . ?
C13 C14 C15 117.1(7) . . ?
C13 C14 I3 121.7(12) . . ?
C15 C14 I3 121.2(13) . . ?
C5 C4 C3 122.2(13) . . ?
C5 C4 N1 120.6(16) . . ?
C3 C4 N1 117.1(15) . . ?
O3 C7 C8 106.6(10) . . ?
O3 C7 C1 119.7(11) . . ?
C8 C7 C1 133.6(12) . . ?
C9 N2 C8 105.2(13) . . ?
C14 C13 F2 119.3(14) . . ?
C14 C13 C12 124.2(13) . . ?
F2 C13 C12 116.5(13) . . ?
C7 O3 C9 106.0(13) . . ?
C11 C10 C15 119.8(13) . . ?
C11 C10 I1 117.9(10) . . ?
C15 C10 I1 122.3(11) . . ?
C6 C1 C2 120.9(12) . . ?
C6 C1 C7 118.2(11) . . ?
C2 C1 C7 120.9(10) . . ?
C4 C5 C6 118.5(13) . . ?
C1 C2 C3 119.5(12) . . ?
C2 C3 C4 117.9(11) . . ?
O1 N1 O2 121.1(15) . . ?
O1 N1 C4 119.6(15) . . ?
O2 N1 C4 119.2(16) . . ?
N2 C8 C7 109.4(12) . . ?
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 C10 2.098(14) . ?
I2 C12 2.065(13) . ?
I3 C14 2.075(7) . ?
F1 C11 1.338(8) . ?
F2 C13 1.361(16) . ?
C12 C13 1.413(18) . ?
C12 C11 1.44(2) . ?
F3 C15 1.316(17) . ?
C6 C1 1.348(19) . ?
C6 C5 1.419(18) . ?
C15 C10 1.34(2) . ?
C15 C14 1.42(2) . ?
C9 N2 1.31(3) . ?
C9 O3 1.346(17) . ?
C11 C10 1.33(2) . ?
C14 C13 1.34(2) . ?
C4 C5 1.32(2) . ?
C4 C3 1.42(2) . ?
C4 N1 1.468(19) . ?
C7 O3 1.340(16) . ?
C7 C8 1.387(17) . ?
C7 C1 1.455(14) . ?
N2 C8 1.340(18) . ?
O1 N1 1.156(19) . ?
C1 C2 1.374(17) . ?
C2 C3 1.401(17) . ?
N1 O2 1.186(18) . ?
