Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of a,B-unsaturated Y-butyrolactams with alkylidene malonates
Yang Yang; Shunxi Dong; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 48 (2012) 5040–; doi:10.1039/c2cc31470c

data_7107689
_publ_section_title
;
 Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction
 of a,B-unsaturated Y-butyrolactams with alkylidene malonates
;
_journal_name_full               Chem.Commun.
_journal_page_first              5040
_journal_paper_doi               10.1039/c2cc31470c
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 Br N O5'
_chemical_formula_sum            'C18 H19 Br N O5'
_chemical_formula_weight         409.25
_chemical_name_systematic
;
?
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-10
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3520(5)
_cell_length_b                   12.0788(10)
_cell_length_c                   21.7041(17)
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    135.05(10)
_cell_measurement_theta_max      29.1589
_cell_measurement_theta_min      2.9592
_cell_volume                     2189.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      135.05(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
1 omega 36.00 63.00 0.6000 35.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 178.0000 -60.0000 45

2 omega -42.00 61.20 0.6000 35.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -19.0000 -120.0000 172

3 omega -6.00 82.20 0.6000 35.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 38.0000 90.0000 147
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0810657000
_diffrn_orient_matrix_UB_12      -0.0167268000
_diffrn_orient_matrix_UB_13      0.0030213000
_diffrn_orient_matrix_UB_21      -0.0179500000
_diffrn_orient_matrix_UB_22      -0.0243516000
_diffrn_orient_matrix_UB_23      0.0288415000
_diffrn_orient_matrix_UB_31      -0.0181281000
_diffrn_orient_matrix_UB_32      -0.0507233000
_diffrn_orient_matrix_UB_33      -0.0150476000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8232
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_coef       0.0013(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1340
_refine_ls_R_factor_gt           0.0958
_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^)+(0.1540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2459
_refine_ls_wR_factor_ref         0.2810
_reflns_number_gt                2129
_reflns_number_total             3798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc31470c.txt
_cod_data_source_block           120104_s1_yy
_cod_database_code               7107689
_chemical_oxdiff_formula         C20H20O6N1Br1
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32