Asymmetric Synthesis of Enantioenriched 6-Hydroxyl Butyrolactams Promoted by N-Heterocyclic Carbene.
Hu, Zhouli; Zhu, Ying; Fu, Zhenqian; Huang, Wei; The Journal of organic chemistry 84 (2019) 10328–10337; doi:10.1021/acs.joc.9b01490

data_4034053
_publ_section_title
;
 Asymmetric Synthesis of Enantioenriched 6-Hydroxyl Butyrolactams Promoted
 by N-Heterocyclic Carbene.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10328
_journal_page_last               10337
_journal_paper_doi               10.1021/acs.joc.9b01490
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 N O4 S'
_chemical_formula_sum            'C24 H23 N O4 S'
_chemical_formula_weight         421.49
_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             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.131(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0345(6)
_cell_length_b                   13.5168(6)
_cell_length_c                   9.3716(6)
_cell_measurement_reflns_used    4082
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.7460
_cell_measurement_theta_min      2.6410
_cell_volume                     1052.43(12)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 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    -83.00  10.00   1.00    2.50    --  -11.59 -37.00  30.00   93
  2  \w    -69.00  18.00   1.00    2.50    --  -11.59 -19.00  90.00   87
  3  \w    -15.00  29.00   1.00    2.50    --  -11.59 -99.00 -60.00   44
  4  \w     40.00  68.00   1.00    2.50    --  -11.59  19.00-150.00   28
  5  \w    -19.00  52.00   1.00    2.50    --   11.74 -99.00 -60.00   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      -0.0780180000
_diffrn_orient_matrix_UB_12      0.0203011000
_diffrn_orient_matrix_UB_13      -0.0204095000
_diffrn_orient_matrix_UB_21      -0.0124835000
_diffrn_orient_matrix_UB_22      -0.0020748000
_diffrn_orient_matrix_UB_23      -0.0795393000
_diffrn_orient_matrix_UB_31      -0.0322445000
_diffrn_orient_matrix_UB_32      -0.0483675000
_diffrn_orient_matrix_UB_33      -0.0052601000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0520
_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       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7771
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.363
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49915
_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    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0414P)^2^+0.0530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                3261
_reflns_number_total             3485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01490_si_002.cif
_cod_data_source_block           single-1
_cod_original_cell_volume        1052.45(12)
_cod_database_code               4034053
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C22(H22), C13(H13), C6(H6), C4(H4A), C17(H17), C20(H20), C5(H5),
 C15(H15), C14(H14), C16(H16), C2(H2), C19(H19), C3(H3)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.447