#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:18:20 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/90/7249023.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_7249023
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, C9 H7 N O'
_chemical_formula_sum            'C15 H7 F4 I2 N O'
_chemical_formula_weight         547.02
_chemical_name_systematic        phox_13tfib
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                103.811(3)
_cell_angle_beta                 95.582(3)
_cell_angle_gamma                101.302(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1512(3)
_cell_length_b                   9.2659(4)
_cell_length_c                   11.0875(4)
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      32.7060
_cell_measurement_theta_min      2.3050
_cell_volume                     788.26(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  42.00   0.50    0.34    --   13.92-117.00  68.00   52
  2  ω     41.00  84.00   0.50    0.34    --   13.92-178.00 -30.00   86
  3  ω     33.00  88.00   0.50    0.34    --   13.92-165.00 -78.00  110
  4  ω    -11.00  43.00   0.50    0.34    --   13.92 -99.00  30.00  108
  5  ω    -15.00  34.00   0.50    0.34    --  -12.98  77.00 -60.00   98
  6  ω      8.00  82.00   0.50    0.34    --   13.92  38.00-150.00  148
  7  ω      2.00  33.00   0.50    0.34    --   13.92  77.00-150.00   62
  8  ω     -9.00  32.00   0.50    0.34    --   13.92  77.00 -30.00   82
  9  ω      5.00  78.00   0.50    0.34    --   13.92  19.00   0.00  146
 10  ω    -30.00  38.00   0.50    0.34    --  -12.98  77.00  60.00  136
 11  ω     -9.00  31.00   0.50    0.34    --   13.92  77.00  90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0154595000
_diffrn_orient_matrix_UB_12      -0.0639080000
_diffrn_orient_matrix_UB_13      0.0253977000
_diffrn_orient_matrix_UB_21      -0.0068069000
_diffrn_orient_matrix_UB_22      -0.0495298000
_diffrn_orient_matrix_UB_23      -0.0607940000
_diffrn_orient_matrix_UB_31      0.0881677000
_diffrn_orient_matrix_UB_32      0.0036602000
_diffrn_orient_matrix_UB_33      0.0100245000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14109
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.033
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.305
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_preparation
'Crystallization from diethyl-ether and hexane (V/V = 1/1)'
_exptl_crystal_recrystallization_method
'Crystallization from diethyl-ether and hexane (V/V = 1/1)'
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0361
_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)+(0.0190P)²+0.4082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0542
_refine_ls_wR_factor_ref         0.0565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3861
_reflns_number_total             4595
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00557k2.cif
_cod_data_source_block           phox_13tfib
_cod_depositor_comments
'Adding full bibliography for 7249013--7249033.cif.'
_cod_original_cell_volume        788.26(5)
_cod_database_code               7249023
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H7 N O I2 F4'
_chemical_oxdiff_usercomment     phox+13tfib
_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_max   0.604
_shelx_estimated_absorpt_t_min   0.287
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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), C8(H8), C3(H3), C5(H5), C4(H4), C9(H9)
;
_olex2_exptl_crystal_mounting_method 'Nylon loop in oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.693
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.65521(2) 0.62617(2) 0.39985(2) 0.02951(6) Uani 1 1 d . . . . .
I2 I 0.51702(3) 1.19026(2) 0.26624(2) 0.03674(6) Uani 1 1 d . . . . .
F4 F 0.4288(2) 0.48834(18) 0.12481(16) 0.0387(4) Uani 1 1 d . . . . .
F1 F 0.6431(2) 0.96879(19) 0.41401(15) 0.0365(4) Uani 1 1 d . . . . .
F2 F 0.3199(2) 0.9264(2) 0.02744(16) 0.0392(4) Uani 1 1 d . . . . .
F3 F 0.2817(2) 0.6223(2) -0.03231(16) 0.0434(4) Uani 1 1 d . . . . .
O1 O 0.9237(3) 0.4889(2) 0.7877(2) 0.0420(5) Uani 1 1 d . . . . .
N1 N 0.8226(3) 0.5117(3) 0.6016(3) 0.0456(7) Uani 1 1 d . . . . .
C12 C 0.4856(3) 0.9546(3) 0.2215(2) 0.0256(5) Uani 1 1 d . . . . .
C1 C 0.9668(3) 0.2306(3) 0.7456(3) 0.0274(6) Uani 1 1 d . . . . .
C7 C 0.9118(3) 0.3519(3) 0.7013(3) 0.0298(6) Uani 1 1 d . . . . .
C10 C 0.5427(3) 0.7266(3) 0.2735(2) 0.0247(5) Uani 1 1 d . . . . .
C13 C 0.3942(3) 0.8638(3) 0.1084(2) 0.0273(6) Uani 1 1 d . . . . .
C11 C 0.5562(3) 0.8818(3) 0.3019(2) 0.0267(5) Uani 1 1 d . . . . .
C15 C 0.4502(3) 0.6409(3) 0.1584(3) 0.0276(6) Uani 1 1 d . . . . .
C14 C 0.3747(3) 0.7081(3) 0.0767(3) 0.0293(6) Uani 1 1 d . . . . .
C2 C 1.0512(3) 0.2562(3) 0.8673(3) 0.0336(6) Uani 1 1 d . . . . .
H2 H 1.071527 0.354284 0.924605 0.040 Uiso 1 1 calc R U . . .
C6 C 0.9375(3) 0.0858(3) 0.6640(3) 0.0338(6) Uani 1 1 d . . . . .
H6 H 0.879236 0.066550 0.581336 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8501(4) 0.3660(4) 0.5891(3) 0.0412(7) Uani 1 1 d . . . . .
H8 H 0.828419 0.288021 0.512497 0.049 Uiso 1 1 calc R U . . .
C3 C 1.1054(4) 0.1385(4) 0.9042(3) 0.0376(7) Uani 1 1 d . . . . .
H3 H 1.163207 0.156695 0.986977 0.045 Uiso 1 1 calc R U . . .
C5 C 0.9923(4) -0.0304(4) 0.7019(3) 0.0383(7) Uani 1 1 d . . . . .
H5 H 0.972267 -0.128743 0.645051 0.046 Uiso 1 1 calc R U . . .
C4 C 1.0767(4) -0.0041(4) 0.8228(3) 0.0371(7) Uani 1 1 d . . . . .
H4 H 1.114152 -0.084203 0.848917 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8668(4) 0.5765(4) 0.7187(4) 0.0484(9) Uani 1 1 d . . . . .
H9 H 0.860325 0.678686 0.754815 0.058 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'
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'
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'
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
C9 O1 C7 104.0(3) . . ?
C9 N1 C8 103.9(3) . . ?
C13 C12 I2 120.83(19) . . ?
C13 C12 C11 117.1(2) . . ?
C11 C12 I2 122.1(2) . . ?
C2 C1 C7 122.0(3) . . ?
C6 C1 C7 119.2(2) . . ?
C6 C1 C2 118.8(2) . . ?
O1 C7 C1 118.0(2) . . ?
C8 C7 O1 107.2(3) . . ?
C8 C7 C1 134.8(3) . . ?
C11 C10 I1 121.15(19) . . ?
C11 C10 C15 116.9(2) . . ?
C15 C10 I1 121.98(19) . . ?
F2 C13 C12 120.2(2) . . ?
F2 C13 C14 118.4(2) . . ?
C14 C13 C12 121.5(2) . . ?
F1 C11 C12 117.8(2) . . ?
F1 C11 C10 118.6(2) . . ?
C10 C11 C12 123.6(2) . . ?
F4 C15 C10 120.4(2) . . ?
F4 C15 C14 118.1(2) . . ?
C14 C15 C10 121.5(2) . . ?
F3 C14 C13 120.2(2) . . ?
F3 C14 C15 120.3(3) . . ?
C13 C14 C15 119.4(2) . . ?
C3 C2 C1 120.0(3) . . ?
C5 C6 C1 120.7(3) . . ?
C7 C8 N1 109.8(3) . . ?
C4 C3 C2 120.8(3) . . ?
C6 C5 C4 120.3(3) . . ?
C3 C4 C5 119.5(3) . . ?
N1 C9 O1 115.1(3) . . ?
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 2.092(2) . ?
I2 C12 2.078(3) . ?
F4 C15 1.344(3) . ?
F1 C11 1.350(3) . ?
F2 C13 1.338(3) . ?
F3 C14 1.339(3) . ?
O1 C7 1.376(4) . ?
O1 C9 1.354(4) . ?
N1 C8 1.388(4) . ?
N1 C9 1.276(5) . ?
C12 C13 1.379(4) . ?
C12 C11 1.386(4) . ?
C1 C7 1.457(4) . ?
C1 C2 1.397(4) . ?
C1 C6 1.389(4) . ?
C7 C8 1.342(4) . ?
C10 C11 1.376(4) . ?
C10 C15 1.387(4) . ?
C13 C14 1.374(4) . ?
C15 C14 1.378(4) . ?
C2 C3 1.386(4) . ?
C6 C5 1.379(4) . ?
C3 C4 1.373(5) . ?
C5 C4 1.388(4) . ?
