An asymmetric iminium ion catalysis-enabled cascade cycloaddition reaction of chromone-oxindole synthons with enals: construction of a spirooxindole-hexahydroxanthone framework.
Zhang, Wen-Hui; Zhou, Yan-You; He, Xue-Wen; Gong, Yi; Liu, Xiong-Li; Zhou, Ying; Organic & biomolecular chemistry 17 (2019) 8369–8373; doi:10.1039/c9ob01670h

data_7157054
_publ_section_title
;
 An asymmetric iminium ion catalysis-enabled cascade cycloaddition
 reaction of chromone-oxindole synthons with enals: construction of a
 spirooxindole-hexahydroxanthone framework.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8369
_journal_page_last               8373
_journal_paper_doi               10.1039/c9ob01670h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C33 H30 Br N O6'
_chemical_formula_sum            'C33 H30 Br N O6'
_chemical_formula_weight         616.49
_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     direct
_audit_creation_date             2019-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.    2019-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.195(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1114(12)
_cell_length_b                   35.404(3)
_cell_length_c                   9.9824(15)
_cell_measurement_reflns_used    1006
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      63.8030
_cell_measurement_theta_min      2.4540
_cell_volume                     2779.2(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      4.00  74.00   1.00    4.00    --   40.98 -99.00 -60.00   70
  2  \w     62.00  93.00   1.00    5.00    --  106.95 -45.00 -60.00   31
  3  \w     97.00 130.00   1.00    5.00    --  106.95 -45.00 -60.00   33
  4  \w     82.00 108.00   1.00    5.00    --  106.95 -61.00  90.00   26
  5  \w     79.00 178.00   1.00    5.00    --  106.95  30.00 120.00   99
  6  \w     94.00 156.00   1.00    5.00    --  106.95 125.00  30.00   62
  7  \w     36.00  87.00   1.00    4.00    --   40.98  38.00-180.00   51
  8  \w     28.00 108.00   1.00    5.00    --  106.95 -95.00   0.00   80
  9  \w     39.00 113.00   1.00    5.00    --  106.95-125.00-120.00   74
 10  \w   -117.00 -10.00   1.00    4.00    --  -40.98 -77.00  60.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0581055000
_diffrn_orient_matrix_UB_12      -0.0399212000
_diffrn_orient_matrix_UB_13      0.0532528000
_diffrn_orient_matrix_UB_21      0.1300764000
_diffrn_orient_matrix_UB_22      0.0173246000
_diffrn_orient_matrix_UB_23      0.1233946000
_diffrn_orient_matrix_UB_31      -0.1346282000
_diffrn_orient_matrix_UB_32      -0.0003165000
_diffrn_orient_matrix_UB_33      0.0851915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.1324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.775
_diffrn_reflns_theta_min         2.496
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.628
_refine_diff_density_min         -1.047
_refine_diff_density_rms         0.094
_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     374
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0809
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+0.0550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3099
_reflns_number_total             5417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01670h2.cif
_cod_data_source_block           2yy-c-3
_cod_depositor_comments          'Adding full bibliography for 7157054.cif.'
_cod_original_cell_volume        2779.1(7)
_cod_database_code               7157054
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.777
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C22(H22), C20(H20), C25(H25), C2(H2), C5(H5), C18(H18),
 C26(H26), C19(H19), C27(H27), C4(H4)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C31(H31A,H31B,
 H31C)
;
_olex2_date_sample_data_collection 2019-03-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.562