An NHC-Catalyzed [3+2] Cyclization of β-Disubstituted Enals with Benzoyl Cyanides
Liu, Wangsheng; Zhang, Linrui; Liao, Xiaoyun; Chen, Jiean; Huang, Yong; Chemical Communications  (2022) –; doi:10.1039/D2CC04025E

data_7130444
_publ_section_title
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 An NHC-Catalyzed [3+2] Cyclization of \b-Disubstituted Enals with Benzoyl
 Cyanides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04025E
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N O3 S'
_chemical_formula_sum            'C20 H19 N O3 S'
_chemical_formula_weight         353.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-03-05 deposited with the CCDC.	2022-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.485(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3004(6)
_cell_length_b                   7.2388(7)
_cell_length_c                   16.6311(14)
_cell_measurement_reflns_used    1689
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.8280
_cell_measurement_theta_min      2.6210
_cell_volume                     866.87(13)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      1.00  28.00   1.00    2.00    --  -11.27 -99.00  30.00   27
  2  \w    -22.00  85.00   1.00    2.00    --   11.59  19.00-180.00  107
  3  \w    -20.00  51.00   1.00    2.00    --   11.59 -99.00-150.00   71
;
_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      -0.0886236000
_diffrn_orient_matrix_UB_12      -0.0341709000
_diffrn_orient_matrix_UB_13      -0.0175435000
_diffrn_orient_matrix_UB_21      0.0398450000
_diffrn_orient_matrix_UB_22      -0.0432685000
_diffrn_orient_matrix_UB_23      -0.0312335000
_diffrn_orient_matrix_UB_31      0.0165732000
_diffrn_orient_matrix_UB_32      -0.0808988000
_diffrn_orient_matrix_UB_33      0.0242623000
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3983
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79429
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0369P)^2^+0.2128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.560
_reflns_Friedel_fraction_full    0.665
_reflns_Friedel_fraction_max     0.665
_reflns_number_gt                2340
_reflns_number_total             2600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04025e2.cif
_cod_data_source_block           zlr
_cod_database_code               7130444
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C10(H10), C14(H14), C9(H9), C13(H13), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              23489
_shelx_hkl_checksum              92405
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.764