Organocatalytic asymmetric Michael addition between 3-subsituted oxindoles and enals catalyzed by camphor sulfonyl hydrazine.
Cheng, Wen-Fu; Chen, Ling-Yan; Xu, Fang-Fang; Lin, Wei-Yu; Ren, Xinfeng; Li, Ya; Organic & biomolecular chemistry 17 (2019) 885–891; doi:10.1039/c8ob02934b

data_7156649
_publ_section_title
;
 Organocatalytic asymmetric Michael addition between 3-subsituted
 oxindoles and enals catalyzed by camphor sulfonyl hydrazine.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              885
_journal_page_last               891
_journal_paper_doi               10.1039/c8ob02934b
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C38 H42 N2 O4'
_chemical_formula_weight         590.73
_chemical_name_systematic
(R)-3-benzyl-3-((R)-4-hydroxybutan-2-yl)indolin-2-one
_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_Hall           'P 62'
_space_group_name_H-M_alt        'P 62'
_symmetry_space_group_name_Hall  'P 62'
_symmetry_space_group_name_H-M   'P 62'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-10-28 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   16.0980(5)
_cell_length_b                   16.0980(5)
_cell_length_c                   10.9326(4)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      139.969
_cell_measurement_theta_min      6.340
_cell_volume                     2453.57(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30554
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.970
_diffrn_reflns_theta_min         3.170
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.016(2)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0468P)^2^+0.1994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2725
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02934b2.cif
_cod_data_source_block           cu_d8v18832_0m
_cod_depositor_comments          'Adding full bibliography for 7156649.cif.'
_cod_original_cell_volume        2453.57(18)
_cod_database_code               7156649
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.930
_shelxl_version_number           2013-4
_shelx_res_checksum              22969
_shelx_hkl_checksum              97544