Facial Access to 2,2-Difluoro-2,3-dihydrofuran Skeleton without Extra Additive: DMF-Promoted Difluorocarbene Formation of ClCF2CO2Na
Chen, Zunsheng; Xie, Xin; Chen, Weiming; Luo, Nianhua; Li, Xiaoning; Yu, Fuchao; Huang, Jiuzhong; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01542K

data_7158911
_publ_section_title
;
 Facial Access to 2,2-Difluoro-2,3-dihydrofuran Skeleton without Extra
 Additive: DMF-Promoted Difluorocarbene Formation of ClCF2CO2Na
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01542K
_journal_year                    2022
_chemical_formula_moiety         'C12 H12 Cl F2 N O'
_chemical_formula_sum            'C12 H12 Cl F2 N O'
_chemical_formula_weight         259.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.098(11)
_cell_angle_beta                 97.747(11)
_cell_angle_gamma                110.017(13)
_cell_formula_units_Z            4
_cell_length_a                   8.8005(12)
_cell_length_b                   11.8789(16)
_cell_length_c                   12.2138(17)
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2000
_cell_measurement_theta_min      2.4260
_cell_volume                     1187.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -57.00  40.00   1.00    2.50    --   12.05 -57.00  60.00   97
  2  \w    -12.00  76.00   1.00    2.50    --   12.05  73.00 -29.00   88
  3  \w    -11.00  85.00   1.00    2.50    --   12.05  57.00-150.00   96
  4  \w     -2.00  12.00   1.00    6.00    --   11.82 -99.00   0.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0638037000
_diffrn_orient_matrix_UB_12      0.0565710000
_diffrn_orient_matrix_UB_13      0.0045456000
_diffrn_orient_matrix_UB_21      -0.0283384000
_diffrn_orient_matrix_UB_22      0.0163354000
_diffrn_orient_matrix_UB_23      0.0471601000
_diffrn_orient_matrix_UB_31      0.0513821000
_diffrn_orient_matrix_UB_32      -0.0241278000
_diffrn_orient_matrix_UB_33      0.0346309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4184
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.421
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1238P)^2^+1.3044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2200
_refine_ls_wR_factor_ref         0.2424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3124
_reflns_number_total             4184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01542k2.cif
_cod_data_source_block           4-1
_cod_database_code               7158911
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.432(4)
 0.568(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C20(H20)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C14(H14), C16(H16), C17(H17),
 C19(H19), C24(H24)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              90708
_shelx_hkl_checksum              11970
_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 2.403
_oxdiff_exptl_absorpt_empirical_full_min 0.629