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_7112411
_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 ad
_chemical_formula_moiety         'C19 H20 Cl3 N O4'
_chemical_formula_sum            'C19 H20 Cl3 N O4'
_chemical_formula_weight         432.71
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-24
_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                   11.6604(10)
_cell_length_b                   11.6604(10)
_cell_length_c                   27.212(2)
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    295.90(10)
_cell_measurement_theta_max      21.3510
_cell_measurement_theta_min      3.5390
_cell_volume                     3204.2(5)
_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      295.90(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.6046
_diffrn_measurement_details
;
  1 omega   23.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512 -154.0000   54.0000 63

  2 omega    6.00   32.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -180.0000 26

  3 omega   25.00   84.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -19.0000  -60.0000 59
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0219757000
_diffrn_orient_matrix_UB_12      -0.0452435000
_diffrn_orient_matrix_UB_13      0.0064549000
_diffrn_orient_matrix_UB_21      0.0019765000
_diffrn_orient_matrix_UB_22      0.0177933000
_diffrn_orient_matrix_UB_23      0.0250123000
_diffrn_orient_matrix_UB_31      -0.0665488000
_diffrn_orient_matrix_UB_32      -0.0502663000
_diffrn_orient_matrix_UB_33      0.0029786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7776
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23804
_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    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.3700
_exptl_crystal_size_mid          0.3500
_exptl_crystal_size_min          0.2400
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         5737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0654
_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^)+(0.0836P)^2^+0.1274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                3946
_reflns_number_total             5737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44059a.txt
_cod_data_source_block           zhangjl0524
_cod_database_code               7112411
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C26(H26), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;