Organocatalytic Reaction of Chromone-Oxindole Synthon: Access to Chromanone-Based Spirocyclohexaneoxindoles with Five Adjacent Stereocenters.
Zuo, Xiong; Liu, Xiong-Li; Wang, Jun-Xin; Yao, Yi-Ming; Zhou, Yan-You; Wei, Qi-Di; Gong, Yi; Zhou, Ying; The Journal of organic chemistry 84 (2019) 6679–6688; doi:10.1021/acs.joc.9b00326

data_4034602
_publ_section_title
;
 Organocatalytic Reaction of Chromone-Oxindole Synthon: Access to
 Chromanone-Based Spirocyclohexaneoxindoles with Five Adjacent
 Stereocenters.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6679
_journal_page_last               6688
_journal_paper_doi               10.1021/acs.joc.9b00326
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H27 N3 O9'
_chemical_formula_sum            'C31 H27 N3 O9'
_chemical_formula_weight         585.55
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5106(4)
_cell_length_b                   8.1242(3)
_cell_length_c                   46.103(3)
_cell_measurement_reflns_used    5321
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4470
_cell_measurement_theta_min      2.8700
_cell_volume                     2813.1(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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   -115.00 -16.00   0.50    0.50    --  -40.73 -38.00 -60.00  198
  2  \w      1.00  82.00   0.50    0.50    --   40.73 -99.00-180.00  162
  3  \w    -31.00  69.00   0.50    0.50    --   40.73 -57.00-180.00  200
  4  \w     31.00 135.00   0.50    0.50    --  106.95 -30.00 150.00  208
  5  \w     31.00 135.00   0.50    0.50    --  106.95 -30.00-120.00  208
  6  \w     25.00 109.00   0.50    0.50    --  106.95 -95.00-150.00  168
  7  \w     94.00 178.00   0.50    0.50    --  106.95 125.00-120.00  168
  8  \w     25.00 109.00   0.50    0.50    --  106.95 -95.00   0.00  168
  9  \w     35.00 136.00   0.50    0.50    --  106.95 -61.00  60.00  202
 10  \w   -113.00 -29.00   0.50    0.50    --  -40.73 -57.00 150.00  168
;
_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      0.1879045000
_diffrn_orient_matrix_UB_12      0.0069646000
_diffrn_orient_matrix_UB_13      -0.0134658000
_diffrn_orient_matrix_UB_21      0.0819741000
_diffrn_orient_matrix_UB_22      -0.0218328000
_diffrn_orient_matrix_UB_23      0.0303715000
_diffrn_orient_matrix_UB_31      -0.0025115000
_diffrn_orient_matrix_UB_32      -0.1880947000
_diffrn_orient_matrix_UB_33      -0.0040176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            14921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.996
_diffrn_reflns_theta_min         1.917
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56886
_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    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0594P)^2^+6.7313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                5170
_reflns_number_total             5535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00326_si_002.cif
_cod_data_source_block           yym_11
_cod_database_code               4034602
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.97
_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:
 C7(H7), C8(H8), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C25(H25), C26(H26), C17(H17), C22(H22), C18(H18), C20(H20), C19(H19),
 C4(H4), C24(H24), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.469
_oxdiff_exptl_absorpt_empirical_full_min 0.562