Organocatalytic asymmetric vinylogous Michael addition of 3-alkylidene oxindoles to α-substituted β-nitroacrylates: Facile construction of chiral all-carbon quaternary center
Zhong, Yuan; Ma, Shixiong; Xu, Zhaoqing; Chang, Min; Wang, Rui; RSC Adv.  (2014) –; doi:10.1039/C4RA09128K

data_7218266
_publ_section_title
;
 Organocatalytic asymmetric vinylogous Michael addition of 3-alkylidene
 oxindoles to \a-substituted \b-nitroacrylates: Facile construction of
 chiral all-carbon quaternary center
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA09128K
_journal_year                    2014
_chemical_formula_moiety         'C21 H19 Cl N2 O5, 0.25(C H2 Cl2)'
_chemical_formula_sum            'C21.25 H19.5 Cl1.5 N2 O5'
_chemical_formula_weight         436.06
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.764(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3843(3)
_cell_length_b                   9.8961(3)
_cell_length_c                   28.9183(7)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    292.1(6)
_cell_measurement_theta_max      69.8060
_cell_measurement_theta_min      4.6510
_cell_volume                     4044.05(18)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.1(6)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -28.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 45

  2 omega  -74.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 38

  3 omega   23.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 49

  4 omega  -61.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 25

  5 omega -110.00  -84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -180.0000 26

  6 omega   44.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  150.0000 35

  7 omega   32.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 93

  8 omega  100.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  151.0000   65.0000 25

  9 omega   37.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 26

 10 omega   27.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000   90.0000 95

 11 omega   77.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 26

 12 omega   23.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 86

 13 omega   73.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 26

 14 omega   50.00  102.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 52

 15 omega   42.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 72

 16 omega   60.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 33

 17 omega  107.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -60.0000 26

 18 omega   44.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -60.0000 50

 19 omega   46.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 40

 20 omega   48.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -90.0000 39

 21 omega   63.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 28

 22 omega  126.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 51

 23 omega   42.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   90.0000 49

 24 omega   96.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   90.0000 77

 25 omega   97.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  122.0000  -96.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0649506000
_diffrn_orient_matrix_UB_12      0.1130793000
_diffrn_orient_matrix_UB_13      -0.0243135000
_diffrn_orient_matrix_UB_21      0.0601454000
_diffrn_orient_matrix_UB_22      0.1058671000
_diffrn_orient_matrix_UB_23      0.0312927000
_diffrn_orient_matrix_UB_31      0.0635953000
_diffrn_orient_matrix_UB_32      0.0152933000
_diffrn_orient_matrix_UB_33      -0.0370440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9128
_diffrn_reflns_point_group_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.571
_diffrn_reflns_theta_min         4.670
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68816
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             1812
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.006(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         6189
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0800P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.530
_reflns_Friedel_fraction_full    0.613
_reflns_Friedel_fraction_max     0.588
_reflns_number_gt                5805
_reflns_number_total             6189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra09128k2.cif
_cod_data_source_block           zhangyuan0608
_cod_original_cell_volume        4044.06(17)
_cod_original_formula_sum        'C21.25 H19.50 Cl1.50 N2 O5'
_cod_database_code               7218266
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H45A(0.5) H45B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C32(H32A,H32B), C41(H41A,H41B), C45(H45A,H45B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16),
 C17(H17), N3(H3A), C24(H24), C25(H25), C26(H26), C27(H27), C35(H35), C36(H36),
 C38(H38), C39(H39)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C40(H40A,H40B,H40C), C44(H44A,H44B,
 H44C)
;
_shelx_res_checksum              62408
_olex2_submission_special_instructions 'No special instructions were received'