Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam.
Zhang, Jinlong; Liu, Xihong; Ma, Xiaojuan; Wang, Rui; Chemical communications (Cambridge, England) 49 (2013) 9329–9331; doi:10.1039/c3cc44059a

data_7112410
_publ_section_title
;
 Organocatalyzed asymmetric vinylogous Michael addition of
 \a,\b-unsaturated \g-butyrolactam.
;
_journal_issue                   81
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9329
_journal_page_last               9331
_journal_paper_doi               10.1039/c3cc44059a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H22 N4 O6'
_chemical_formula_sum            'C22 H22 N4 O6'
_chemical_formula_weight         438.44
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   19.4670(10)
_cell_length_b                   19.4670(10)
_cell_length_c                   10.8548(6)
_cell_measurement_reflns_used    2275
_cell_measurement_temperature    296.24(10)
_cell_measurement_theta_max      20.8630
_cell_measurement_theta_min      3.6910
_cell_volume                     3562.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      296.24(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.7908
_diffrn_measurement_details
;
  1 omega  -25.00   42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000  120.0000 67

  2 omega  -22.00   56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000    0.0000 78
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0212528000
_diffrn_orient_matrix_UB_12      -0.0228668000
_diffrn_orient_matrix_UB_13      0.0518798000
_diffrn_orient_matrix_UB_21      -0.0192098000
_diffrn_orient_matrix_UB_22      0.0226956000
_diffrn_orient_matrix_UB_23      0.0055380000
_diffrn_orient_matrix_UB_31      -0.0307888000
_diffrn_orient_matrix_UB_32      -0.0270304000
_diffrn_orient_matrix_UB_33      -0.0393573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8537
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.3300
_exptl_crystal_size_mid          0.2200
_exptl_crystal_size_min          0.1800
_platon_squeeze_details
;
;
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0869
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2303
_refine_ls_wR_factor_ref         0.2721
_reflns_number_gt                2620
_reflns_number_total             4102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44059a.txt
_cod_data_source_block           zhangjl0510
_cod_database_code               7112410
_reflns_odcompleteness_completeness 99.77
_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. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;