Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality.
Yuan, Xi; Wu, Xudong; Peng, Fei; Yang, Haijun; Zhu, Changjin; Fu, Hua; Chemical communications (Cambridge, England) 56 (2020) 12648–12651; doi:10.1039/d0cc05432a

data_7127321
_publ_section_title
;
 Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with
 both axial and central chirality.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12648
_journal_page_last               12651
_journal_paper_doi               10.1039/d0cc05432a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H22 N2 O5'
_chemical_formula_sum            'C30 H22 N2 O5'
_chemical_formula_weight         490.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-22 deposited with the CCDC.	2020-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.549(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8477(2)
_cell_length_b                   14.2309(2)
_cell_length_c                   9.63710(10)
_cell_measurement_reflns_used    5687
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      71.3030
_cell_measurement_theta_min      4.5860
_cell_volume                     1207.73(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -55.00 -18.00   1.00    1.00    --  -40.81 125.00-150.00   37
  2  \w   -115.00 -17.00   1.00    1.00    --  -40.81 -39.00  56.00   98
  3  \w    -91.00 -65.00   1.00    1.00    --  -40.81 125.00-150.00   26
  4  \w   -110.00 -27.00   1.00    1.00    --  -40.81 -38.00 150.00   83
  5  \w      7.00  82.00   1.00    1.00    --   40.81 -99.00 -30.00   75
  6  \w    124.00 167.00   1.00    1.00    --  100.91  61.00-120.00   43
  7  \w     30.00  65.00   1.00    1.00    --  100.91 -45.00  90.00   35
  8  \w     31.00  83.00   1.00    1.00    --  100.91 -77.00  90.00   52
  9  \w     41.00 123.00   1.00    1.00    --  100.91 -45.00-180.00   82
 10  \w     54.00 110.00   1.00    1.00    --  100.91 -95.00  60.00   56
 11  \w     32.00  58.00   1.00    1.00    --  100.91 -61.00 -60.00   26
 12  \w     87.00 121.00   1.00    1.00    --  100.91 -45.00  90.00   34
 13  \w     39.00 127.00   1.00    1.00    --  100.91 -45.00 -60.00   88
 14  \w     30.00 110.00   1.00    1.00    --  100.91 -95.00-180.00   80
 15  \w     55.00 110.00   1.00    1.00    --  100.91 -95.00 -60.00   55
 16  \w     13.00 172.00   1.00    1.00    --  100.91   0.00-120.00  159
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1587583000
_diffrn_orient_matrix_UB_12      -0.0361087000
_diffrn_orient_matrix_UB_13      0.0270017000
_diffrn_orient_matrix_UB_21      -0.0655368000
_diffrn_orient_matrix_UB_22      0.0391599000
_diffrn_orient_matrix_UB_23      -0.1424001000
_diffrn_orient_matrix_UB_31      0.0333736000
_diffrn_orient_matrix_UB_32      -0.0942017000
_diffrn_orient_matrix_UB_33      -0.0692892000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7961
_diffrn_reflns_point_group_measured_fraction_full 0.743
_diffrn_reflns_point_group_measured_fraction_max 0.724
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.409
_diffrn_reflns_theta_min         4.610
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0588P)^2^+0.1718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.407
_reflns_Friedel_fraction_full    0.463
_reflns_Friedel_fraction_max     0.438
_reflns_number_gt                3298
_reflns_number_total             3401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05432a2.cif
_cod_data_source_block           20190115yuanxi
_cod_depositor_comments          'Adding full bibliography for 7127321.cif.'
_cod_database_code               7127321
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N006(H006), N007(H007), C00K(H00K), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010), C011(H011)
2.b Idealised Me refined as rotating group:
 C00Z(H00A,H00B,H00C)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O005(H005)
;
_shelx_res_checksum              1176
_shelx_hkl_checksum              73714
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.710