H/F replacement in secondary alcohols of sydnones as examples of isostructural OH⋯OC hydrogen bonded dimer structures
Dumitrascu, Florea; Popa, Marcel Mirel; Shova, Sergiu; Man, Isabela C.; Draghici, Constantin; Caira, Mino R.; CrystEngComm 27 (2025) 5162–5172; doi:10.1039/D5CE00492F

data_7250608
_publ_section_title
;
 H/F replacement in secondary alcohols of sydnones as examples of
 isostructural OH&#x22EF;O&#xE001;C hydrogen bonded dimer structures
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              5162
_journal_page_last               5172
_journal_paper_doi               10.1039/D5CE00492F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C10 H9 F N2 O3'
_chemical_formula_sum            'C10 H9 F N2 O3'
_chemical_formula_weight         224.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-03-11 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8617(14)
_cell_length_b                   6.9928(8)
_cell_length_c                   19.4887(14)
_cell_measurement_reflns_used    1590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2420
_cell_measurement_theta_min      2.0780
_cell_volume                     2025.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_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    -22.00  19.00   1.00   15.00    --  -15.60 -99.00 120.00   41
  2  \w     -2.00  25.00   1.00   15.00    --   17.79 -57.00 -90.00   27
  3  \w    -34.00  -6.00   1.00   15.00    --  -15.60 -57.00-150.00   28
  4  \w      4.00  76.00   1.00   15.00    --   17.79  57.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0115130000
_diffrn_orient_matrix_UB_12      0.0213386000
_diffrn_orient_matrix_UB_13      0.0344728000
_diffrn_orient_matrix_UB_21      0.0403914000
_diffrn_orient_matrix_UB_22      0.0437673000
_diffrn_orient_matrix_UB_23      -0.0114016000
_diffrn_orient_matrix_UB_31      -0.0226206000
_diffrn_orient_matrix_UB_32      0.0889893000
_diffrn_orient_matrix_UB_33      -0.0027061000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5671
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.090
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0015(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0607
_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/[\s^2^(Fo^2^)+(0.0508P)^2^+0.9221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1401
_reflns_number_total             1795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00492f2.cif
_cod_data_source_block           shi_3473_fldu
_cod_depositor_comments
'Adding full bibliography for 7250606--7250610.cif.'
_cod_database_code               7250608
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N4 O2 F1'
_chemical_oxdiff_usercomment     RT_104
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              15417
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.915