Evaluation of halogen bonding proclivity of oxazole derivatives carrying multiple acceptor sites in cocrystals with perfluorinated iodobenzenes
Sušanj, Ruđer; Bedeković, Nikola; Cerovski, Sara; Baus Topić, Nea; Nemec, Vinko; Cinčić, Dominik; CrystEngComm 26 (2024) 4137–4145; doi:10.1039/D4CE00557K

data_7249017
_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
_chemical_name_systematic
'3-pyridyloxazole 2,4,5,6-tetrafluoro-1,3-diiodobenzene'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-18
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.99780(10)
_cell_length_b                   7.7740(2)
_cell_length_c                   32.9740(7)
_cell_measurement_reflns_used    19764
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      33.3580
_cell_measurement_theta_min      2.4680
_cell_volume                     1537.48(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 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -38.00  37.00   0.50    0.83    --   13.76 -77.00-120.00  150
  2  \w    -62.00  -9.00   0.50    0.83    --   13.76 -19.00-180.00  106
  3  \w     -7.00  36.00   0.50    0.83    --   13.76  77.00 -60.00   86
  4  \w     -7.00  18.00   0.50    0.83    --   13.76  77.00  90.00   50
  5  \w    -30.00  37.00   0.50    0.83    --   13.76 -77.00  90.00  134
  6  \w    -38.00   5.00   0.50    0.83    --  -12.98 -77.00 120.00   86
  7  \w    -16.00  45.00   0.50    0.83    --   13.76 -99.00 150.00  122
  8  \w     40.00  67.00   0.50    0.83    --   13.76-178.00 -90.00   54
  9  \w      3.00  42.00   0.50    0.83    --   13.76-111.00 -33.00   78
 10  \w    -85.00 -23.00   0.50    0.83    --  -12.98 -57.00 -30.00  124
 11  \w    -36.00  29.00   0.50    0.83    --  -12.98  77.00 -60.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0211748000
_diffrn_orient_matrix_UB_12      -0.0223607000
_diffrn_orient_matrix_UB_13      -0.0204951000
_diffrn_orient_matrix_UB_21      0.1135824000
_diffrn_orient_matrix_UB_22      0.0152137000
_diffrn_orient_matrix_UB_23      -0.0048009000
_diffrn_orient_matrix_UB_31      0.0252804000
_diffrn_orient_matrix_UB_32      -0.0871496000
_diffrn_orient_matrix_UB_33      0.0044197000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            28925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.471
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67841
_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    2.367
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1016
_exptl_crystal_preparation       'Crystallization from MTBE'
_exptl_crystal_recrystallization_method 'Crystalllization from MTBE'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.129(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0130P)^2^+0.7192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0361
_refine_ls_wR_factor_ref         0.0364
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4347
_reflns_number_total             4483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00557k2.cif
_cod_data_source_block           pox_13tfib
_cod_depositor_comments
'Adding full bibliography for 7249013--7249033.cif.'
_cod_database_code               7249017
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O I F H'
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.340
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.871(19)
 0.129(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C5(H5), C3(H3), C4(H4), C7(H7)
;
_shelx_res_checksum              77660
_shelx_hkl_checksum              89514
_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.779