Organocatalytic Enantioselective Vinylogous Michael-Aldol Cascade for the Synthesis of Spirocyclic Compounds.
Mondal, Santigopal; Mukherjee, Subrata; Yetra, Santhivardhana Reddy; Gonnade, Rajesh G.; Biju, Akkattu T.; Organic letters 19 (2017) 4367–4370; doi:10.1021/acs.orglett.7b02085

data_1547063
_publ_section_title
;
 Organocatalytic Enantioselective Vinylogous Michael-Aldol Cascade for the
 Synthesis of Spirocyclic Compounds.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4367
_journal_page_last               4370
_journal_paper_doi               10.1021/acs.orglett.7b02085
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H25 N3 O4'
_chemical_formula_sum            'C32 H25 N3 O4'
_chemical_formula_weight         515.55
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9278(8)
_cell_length_b                   13.8213(12)
_cell_length_c                   19.0453(15)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.42
_cell_measurement_theta_min      33.46
_cell_volume                     2613.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23261
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.277
_diffrn_reflns_theta_min         5.642
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.102
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
;
 Flack x determined using 2098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0416P)^2^+0.2600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                5023
_reflns_number_total             5209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02085_si_002.cif
_cod_data_source_block           cu_SUM_SE_184NEW_0m
_cod_database_code               1547063
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.832
_shelx_estimated_absorpt_t_max   0.895
_shelx_res_checksum              36822
_shelx_hkl_checksum              47667