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_7250607
_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 H7 F N2 O3'
_chemical_formula_sum            'C10 H7 F N2 O3'
_chemical_formula_weight         222.18
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-09
_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                   11.3436(6)
_cell_length_b                   8.3777(4)
_cell_length_c                   20.5336(11)
_cell_measurement_reflns_used    1869
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.66
_cell_volume                     1951.38(17)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_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    -23.00  18.00   1.00   20.00    --  -15.29 -90.00 -25.00   41
  2  \w    -49.00  32.00   1.00   20.00    --  -15.29  90.00  89.00   81
  3  \w     12.00  37.00   1.00   20.00    --   17.71  77.00-180.00   25
  4  \w     -8.00  37.00   1.00   20.00    --   17.71  77.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0345481000
_diffrn_orient_matrix_UB_12      0.0647191000
_diffrn_orient_matrix_UB_13      0.0114717000
_diffrn_orient_matrix_UB_21      0.0106540000
_diffrn_orient_matrix_UB_22      0.0417436000
_diffrn_orient_matrix_UB_23      -0.0294623000
_diffrn_orient_matrix_UB_31      -0.0510180000
_diffrn_orient_matrix_UB_32      -0.0350977000
_diffrn_orient_matrix_UB_33      -0.0139457000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         1.984
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.126
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0391P)^2^+0.2046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1314
_reflns_number_total             1722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00492f2.cif
_cod_data_source_block           shi_6702_fldu_auto
_cod_depositor_comments
'Adding full bibliography for 7250606--7250610.cif.'
_cod_original_cell_volume        1951.37(17)
_cod_database_code               7250607
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N2O3F1
_chemical_oxdiff_usercomment     'FA_63, CSD: JADCOH'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_diffrn_oxdiff_digest_hkl
;
0132da43e87436a998c068de8c363739a9cedd
;
_diffrn_oxdiff_digest_od_ed
;

;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              3278
_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 1.064
_oxdiff_exptl_absorpt_empirical_full_min 0.942