A catalytic asymmetric hetero-Diels-Alder reaction of olefinic azlactones and isatins: facile access to chiral spirooxindole dihydropyranones
Tai-Ping Gao; Jun-Bing Lin; Xiu-Qin Hu; Peng-Fei Xu; Chem.Commun. 50 (2014) 8934–; doi:10.1039/C4cc03896G

data_7115396
_publ_section_title
;
 A catalytic asymmetric hetero-Diels-Alder reaction of olefinic azlactones
 and isatins: facile access to chiral spirooxindole dihydropyranones
;
_journal_name_full               Chem.Commun.
_journal_page_first              8934
_journal_paper_doi               10.1039/C4cc03896G
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration none
_chemical_formula_moiety         'C27 H21 Br N2 O4'
_chemical_formula_sum            'C27 H21 Br N2 O4'
_chemical_formula_weight         517.37
_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
_audit_creation_date             2014-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3254(6)
_cell_length_b                   10.3246(8)
_cell_length_c                   26.4259(17)
_cell_measurement_reflns_used    1497
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.9410
_cell_measurement_theta_min      3.6170
_cell_volume                     2817.1(3)
_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)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0245830000
_diffrn_orient_matrix_UB_12      0.0307416000
_diffrn_orient_matrix_UB_13      -0.0219955000
_diffrn_orient_matrix_UB_21      -0.0150118000
_diffrn_orient_matrix_UB_22      -0.0613730000
_diffrn_orient_matrix_UB_23      -0.0105356000
_diffrn_orient_matrix_UB_31      -0.0623782000
_diffrn_orient_matrix_UB_32      0.0026483000
_diffrn_orient_matrix_UB_33      0.0112036000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_unetI/netI     0.1779
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15851
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         3.037
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12705
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.030(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.796
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.796
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0641P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2028
_reflns_number_total             5465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc03896g3.cif
_cod_data_source_block           gaotp_0313-sr
_cod_original_cell_volume        2817.2(3)
_cod_database_code               7115396
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), N2(H2), C23(H23), C21(H21), C11(H11), C13(H13), C1(H1), C3(H3),
 C14(H14), C5(H5), C4(H4), C2(H2A), C12(H12), C15(H15)
2.c Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              47376
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'