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_4034054
_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_formula_moiety         'C24 H27 N O4 S'
_chemical_formula_sum            'C24 H27 N O4 S'
_chemical_formula_weight         425.52
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.067(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2321(15)
_cell_length_b                   7.4711(9)
_cell_length_c                   13.3738(16)
_cell_measurement_reflns_used    4701
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.73
_cell_volume                     1148.0(2)
_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_temperature      300.66
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10231
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.783
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0726P)^2^+0.3004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                4041
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01490_si_003.cif
_cod_data_source_block           1111
_cod_database_code               4034054
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C1-O1
 1.4 with sigma of 0.02
 C00C-O1 \\sim C00C-O1A
 with sigma of 0.04
 C00C-C1 \\sim C00C-C1A
 with sigma of 0.02
 C1-O1 \\sim C1A-O1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
4. Others
 Sof(H00E)=Sof(H00D)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(O1A)=Sof(H1AC)=1-FVAR(1)
 Sof(H00A)=Sof(H00C)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(O1)=Sof(H1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C009(H009), C00D(H00F), C00J(H00J)
5.b Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00C), C00C(H00E,H00D), C1(H1A,H1B), C1A(H1AA,H1AB)
5.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00F(H00G), C00H(H00H), C00I(H00I),
 C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
5.d Tetrahedral OH refined with riding coordinates:
 O004(H004), O1(H1), O1A(H1AC)
5.e Idealised Me refined as rotating group:
 C00N(H00K,H00N,H00O)
;
_shelx_res_checksum              45487
_shelx_hkl_checksum              88433
_olex2_submission_special_instructions 'No special instructions were received'