Hydrogen-Bond-Directed Formal [5 + 1] Annulations of Oxindoles with Ester-Linked Bisenones: Facile Access to Chiral Spirooxindole δ-Lactones.
Zhao, Shuai; Lin, Jun-Bing; Zhao, Yuan-Yuan; Liang, Yong-Min; Xu, Peng-Fei; Organic letters 16 (2014) 1802–1805; doi:10.1021/ol500547e

data_1513939
_publ_section_title
;
 Hydrogen-Bond-Directed Formal [5 + 1] Annulations of Oxindoles with
 Ester-Linked Bisenones: Facile Access to Chiral Spirooxindole
 \d-Lactones.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1802
_journal_page_last               1805
_journal_paper_doi               10.1021/ol500547e
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration none
_chemical_formula_moiety         'C29 H24 Br N O5'
_chemical_formula_sum            'C29 H24 Br N O5'
_chemical_formula_weight         546.40
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-08-02
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9150(5)
_cell_length_b                   11.1839(5)
_cell_length_c                   25.1030(11)
_cell_measurement_reflns_used    2640
_cell_measurement_temperature    291.31(12)
_cell_measurement_theta_max      22.7500
_cell_measurement_theta_min      3.7280
_cell_volume                     2502.9(2)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      291.31(12)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.8656
_diffrn_measurement_details
;
  1 omega  -20.00   16.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000 -120.0000 36

  2 omega  -43.00  -15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   57.0000  -90.0000 28

  3 omega   -3.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  150.0000 91

  4 omega   21.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000 -120.0000 55
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0059250000
_diffrn_orient_matrix_UB_12      -0.0072329000
_diffrn_orient_matrix_UB_13      -0.0279918000
_diffrn_orient_matrix_UB_21      0.0629069000
_diffrn_orient_matrix_UB_22      0.0380075000
_diffrn_orient_matrix_UB_23      -0.0036247000
_diffrn_orient_matrix_UB_31      0.0484126000
_diffrn_orient_matrix_UB_32      -0.0502123000
_diffrn_orient_matrix_UB_33      0.0013225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8601
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.033
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67446
_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_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0328P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                3419
_reflns_number_total             4816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500547e_si_001.cif
_cod_data_source_block           zhaoshuai0718
_cod_database_code               1513939
_reflns_odcompleteness_completeness 99.63
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C21(H21), C22(H22),
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_hkl_checksum              70498
_shelx_res_checksum              52767
_shelxl_version_number           2013-2