Organocatalytic enantioselective direct vinylogous Michael addition of γ-substituted deconjugate butenolides to azadienes
Lin, Wei; Lin, Xiao; Cheng, Yuyu; Chang, Xiaoyong; Zhou, San; Li, Pengfei; Li, Wenjun; Organic Chemistry Frontiers 6 (2019) 2452–; doi:10.1039/C9QO00597H

data_1554957
_publ_section_title
;
 Organocatalytic enantioselective direct vinylogous Michael addition of
 \g-substituted deconjugate butenolides to azadienes
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2452
_journal_paper_doi               10.1039/C9QO00597H
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 Cl N O5 S'
_chemical_formula_sum            'C27 H22 Cl N O5 S'
_chemical_formula_weight         507.96
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-24 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1603(5)
_cell_length_b                   10.1730(4)
_cell_length_c                   23.5179(10)
_cell_measurement_reflns_used    9045
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.65
_cell_volume                     2430.83(18)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.1
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            35426
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.181
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0867 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.9276. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.030(16)
_refine_ls_extinction_coef       0.0066(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0313P)^2^+0.8530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5340
_reflns_number_total             5612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00597h2.cif
_cod_data_source_block           cxy0570_0m
_cod_database_code               1554957
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'