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_7249020
_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         '2(C6 F4 I2), C9 H7 N O'
_chemical_formula_sum            'C21 H7 F8 I4 N O'
_chemical_formula_weight         948.88
_chemical_name_systematic        phen-ox_14tfib_2
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 127.927(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.7446(14)
_cell_length_b                   8.7558(2)
_cell_length_c                   24.0108(11)
_cell_measurement_reflns_used    27837
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      33.8840
_cell_measurement_theta_min      2.4670
_cell_volume                     4932.6(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      170.00(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    -86.00   1.00   0.50    3.00    --  -12.98 -74.00  47.00  174
  2  \w    -58.00   1.00   0.50    3.00    --   13.76 -74.00  47.00  118
  3  \w     -7.00  73.00   0.50    3.00    --   13.76  74.00 176.00  160
  4  \w     -1.00  81.00   0.50    3.00    --   13.76  57.00 -30.00  164
  5  \w     44.00  87.00   0.50    3.00    --   13.76 178.00 -30.00   86
  6  \w    -53.00 -27.00   0.50    3.00    --   13.76 -19.00 -30.00   52
  7  \w    -22.00   5.00   0.50    3.00    --   13.76 -19.00 -30.00   54
  8  \w     -9.00  33.00   0.50    3.00    --   13.76  77.00-120.00   84
  9  \w     -9.00  35.00   0.50    3.00    --   13.76  77.00   0.00   88
 10  \w     45.00  86.00   0.50    3.00    --   13.76 178.00-150.00   82
 11  \w    -55.00  12.00   0.50    3.00    --   13.76 -38.00  90.00  134
 12  \w     39.00  64.00   0.50    3.00    --   13.76-178.00   0.00   50
;
_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      0.0272995000
_diffrn_orient_matrix_UB_12      -0.0040845000
_diffrn_orient_matrix_UB_13      0.0081792000
_diffrn_orient_matrix_UB_21      -0.0125203000
_diffrn_orient_matrix_UB_22      -0.0295298000
_diffrn_orient_matrix_UB_23      -0.0341816000
_diffrn_orient_matrix_UB_31      -0.0034327000
_diffrn_orient_matrix_UB_32      0.0753107000
_diffrn_orient_matrix_UB_33      -0.0129476000
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            48908
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38769
_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    2.555
_exptl_crystal_description       plate
_exptl_crystal_F_000             3456
_exptl_crystal_preparation       'Crystallization from'
_exptl_crystal_recrystallization_method 'Crystallization from'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.074
_refine_diff_density_max         1.720
_refine_diff_density_min         -1.612
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0178P)^2^+15.8162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6133
_reflns_number_total             7186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00557k2.cif
_cod_data_source_block           phox_12tfib_2
_cod_depositor_comments
'Adding full bibliography for 7249013--7249033.cif.'
_cod_original_cell_volume        4932.6(5)
_cod_database_code               7249020
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H7 N O I2 F4'
_chemical_oxdiff_usercomment     phox+12tfib
_shelx_estimated_absorpt_t_max   0.703
_shelx_estimated_absorpt_t_min   0.240
_reflns_odcompleteness_completeness 99.94
_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:
 C6(H6), C5(H5), C2(H2), C9(H9), C3(H3), C4(H4), C8(H8)
;
_shelx_res_checksum              32249
_shelx_hkl_checksum              68725
_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 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.682