Organocatalytic Tandem Enantioselective Michael-Cyclization of Isatin-Derived β, γ-Unsaturated α-Ketoesters with 3-Hydroxy-4H-Chromen-4-One or 2-Hydroxy-1,4-Naphthoquinone Derivatives
Yin, Shao-Jie; Zhang, Shao-Yun; Zhang, Jun-Qi; Sun, Bing-Bing; Fan, Wei-Tai; Wu, Bing; Wang, Xingwang; RSC Adv.  (2016) –; doi:10.1039/C6RA17400K

data_7226301
_publ_section_title
;
 Organocatalytic Tandem Enantioselective Michael-Cyclization of
 Isatin-Derived \b, \g-Unsaturated \a-Ketoesters with
 3-Hydroxy-4H-Chromen-4-One or 2-Hydroxy-1,4-Naphthoquinone Derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA17400K
_journal_year                    2016
_chemical_formula_moiety         '2(C23 H18 Br N O7), 0.5(C6H14)'
_chemical_formula_sum            'C49 H43 Br2 N2 O14'
_chemical_formula_weight         1036.62
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-09 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.421(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.7894(8)
_cell_length_b                   17.4413(12)
_cell_length_c                   10.9644(7)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7830
_cell_measurement_theta_min      4.7670
_cell_volume                     2430.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  -27.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000 -150.0000 58

  2 omega -111.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -77.0000  -90.0000 102

  3 omega   -9.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000 -120.0000 39

  4 omega    9.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343   77.0000  150.0000 27

  5 omega   87.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343   77.0000  150.0000 25

  6 omega   46.00   86.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   30.0000 40

  7 omega   32.00   97.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -120.0000 65

  8 omega   38.00   64.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -180.0000 26

  9 omega   38.00   64.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -30.0000 26

 10 omega  112.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  178.0000  -30.0000 31

 11 omega   47.00   82.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -94.0000 -180.0000 35

 12 omega   78.00  166.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   30.0000 -120.0000 88

 13 omega   41.00   94.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  -60.0000 53

 14 omega   29.00   90.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   90.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0264197000
_diffrn_orient_matrix_UB_12      -0.0337765000
_diffrn_orient_matrix_UB_13      -0.1297125000
_diffrn_orient_matrix_UB_21      -0.1181218000
_diffrn_orient_matrix_UB_22      0.0108716000
_diffrn_orient_matrix_UB_23      0.0104289000
_diffrn_orient_matrix_UB_31      0.0047349000
_diffrn_orient_matrix_UB_32      0.0808884000
_diffrn_orient_matrix_UB_33      -0.0555765000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9219
_diffrn_reflns_theta_full        73.37
_diffrn_reflns_theta_max         73.37
_diffrn_reflns_theta_min         4.30
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0653
_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^)+(0.1156P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2246
_reflns_number_gt                3166
_reflns_number_total             4746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra17400k2.cif
_cod_data_source_block           g160108a
_cod_database_code               7226301
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C25-C26 = C25-C24
 1.5 with sigma of 0.01
3. Rigid bond restraints
 C24, C26, C25
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C24 \\sim C26 \\sim C25: within 1.7A with sigma of 0.005 and sigma for terminal
atoms of 0.01
5. Others
 Fixed Sof: C24(0.5) C26(0.5) C25(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C11(H11A,H11B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C0AA(H0AA), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C)
6.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_date_sample_data_collection 2015-10-19
_olex2_submission_special_instructions 'No special instructions were received'