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_7250609
_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 H10 N2 O3'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-03-19 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.053(4)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   41.5257(16)
_cell_length_b                   12.1880(5)
_cell_length_c                   7.6472(4)
_cell_measurement_reflns_used    3494
_cell_measurement_temperature    288(19)
_cell_measurement_theta_max      69.1560
_cell_measurement_theta_min      4.1940
_cell_volume                     3870.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.137a 64-bit (release 10-09-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_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      air
_diffrn_ambient_temperature      288(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -50.00  20.00   0.50   40.00    --  -47.51  59.00  96.00  140
  2  \w     39.00  77.00   0.50   50.00    --  106.68 -72.00 102.00   76
  3  \w     39.00 103.00   0.50   50.00    --  106.68 -96.00-141.00  128
  4  \w     91.00 177.00   0.50   50.00    --  106.68  59.00  96.00  172
  5  \w    -25.00  28.00   0.50   40.00    --  -47.51  19.00-120.00  106
  6  \w    -14.00  21.00   0.50   40.00    --  -47.51  19.00 -30.00   70
  7  \w     -7.00  20.00   0.50   40.00    --   47.51 -19.00 -60.00   54
  8  \w    -49.00 -23.00   0.50   50.00    --  -91.75  45.00-180.00   52
  9  \w   -114.00 -85.00   0.50   50.00    --  -91.75 -45.00-150.00   58
 10  \w   -163.00-122.00   0.50   50.00    --  -91.75 -45.00-150.00   82
 11  \w    -49.00 -21.00   0.50   50.00    --  -91.75  45.00 -60.00   56
 12  \w    -51.00 -26.00   0.50   50.00    --  -91.75  45.00  30.00   50
 13  \w     34.00  59.00   0.50   50.00    --  106.68 -59.00 -43.00   50
 14  \w     53.00  81.00   0.50   50.00    --  106.68 -77.00 -90.00   56
 15  \w   -107.00 -35.00   0.50   40.00    --  -47.64 -68.00 -45.00  144
 16  \w    -18.00   8.00   0.50   40.00    --   47.64 -19.00 -90.00   52
 17  \w   -163.00-130.00   0.50   50.00    --  -91.75 -95.00-150.00   66
 18  \w   -116.00 -87.00   0.50   50.00    --  -91.75-125.00-150.00   58
 19  \w    -47.00 -21.00   0.50   50.00    --  -91.75  45.00 -30.00   52
 20  \w   -117.00 -89.00   0.50   50.00    --  -91.75 -95.00-150.00   56
 21  \w    -49.00 -23.00   0.50   50.00    --  -91.75  45.00-120.00   52
 22  \w     35.00  70.00   0.50   50.00    --  106.68 -61.00 -30.00   70
 23  \w     41.00  67.00   0.50   50.00    --  106.68 -61.00-150.00   52
 24  \w     37.00  71.00   0.50   50.00    --  106.68 -61.00   0.00   68
 25  \w     38.00  69.00   0.50   50.00    --  106.68 -61.00  30.00   62
 26  \w    140.00 170.00   0.50   50.00    --  106.68  15.00  90.00   60
 27  \w     93.00 128.00   0.50   50.00    --  106.68  15.00  90.00   70
 28  \w     72.00 104.00   0.50   50.00    --  106.68 -95.00  90.00   64
 29  \w    -85.00 -41.00   0.50   50.00    --  -91.75  69.00  86.00   88
 30  \w    -13.00  23.00   0.50   40.00    --  -47.64  19.00  90.00   72
 31  \w    -14.00  12.00   0.50   40.00    --   47.64 -19.00 -90.00   52
 32  \w    -51.00 -26.00   0.50   50.00    --  -91.75  45.00 120.00   50
 33  \w    -71.00 -46.00   0.50   50.00    --  -91.75  61.00  60.00   50
 34  \w     98.00 124.00   0.50   50.00    --  106.68  45.00 -60.00   52
 35  \w    142.00 168.00   0.50   50.00    --  106.68  45.00 -60.00   52
 36  \w    115.00 158.00   0.50   50.00    --  106.68  61.00   0.00   86
;
_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      0.0250808000
_diffrn_orient_matrix_UB_12      -0.0920046000
_diffrn_orient_matrix_UB_13      0.0234426000
_diffrn_orient_matrix_UB_21      -0.0049218000
_diffrn_orient_matrix_UB_22      -0.0347548000
_diffrn_orient_matrix_UB_23      -0.1919640000
_diffrn_orient_matrix_UB_31      0.0268712000
_diffrn_orient_matrix_UB_32      0.0793852000
_diffrn_orient_matrix_UB_33      -0.0567400000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            30898
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.193
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         6826
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1703
_refine_ls_R_factor_gt           0.1195
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.029
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2992
_refine_ls_wR_factor_ref         0.3429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3931
_reflns_number_total             6826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00492f2.cif
_cod_data_source_block           monocl
_cod_depositor_comments
'Adding full bibliography for 7250606--7250610.cif.'
_cod_original_cell_volume        3870.3(3)
_cod_database_code               7250609
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N2O2
_chemical_oxdiff_usercomment     'DC-470 '
_diffrn_oxdiff_ac3_digest_hkl    41b4b73ebd5d4db7e0e51647ffd288ec7a6caa
_diffrn_oxdiff_digest_hkl
;
4342d1e7fdf9a6452a3091c45ecf368d1f39c9
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.504(4)
 0.496(4)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C6B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1A(H1AA), C1C(H1CA), C1D(H1DA), C1B(H1BA)
4.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C9A(H9A), C4C(H4C), C5C(H5C),
 C7C(H7C), C8C(H8C), C9C(H9C), C4D(H4D), C5D(H5D), C7D(H7D), C8D(H8D), C9D(H9D),
  C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), C9B(H9B)
4.c Idealised Me refined as rotating group:
 C2A(H2AA,H2AB,H2AC), C2C(H2CA,H2CB,H2CC), C2D(H2DA,H2DB,H2DC), C2B(H2BA,H2BB,
 H2BC)
4.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1C(H1C), O1D(H1D), O1B(H1B)
;
_shelx_res_checksum              43997
_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 2.949
_oxdiff_exptl_absorpt_empirical_full_min 0.444