Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones.
Lu, Fo-Yun; Chen, Yu-Jue; Chen, Yuan; Ding, Xuan; Guan, Zhi; He, Yan-Hong; Chemical communications (Cambridge, England) 56 (2020) 623–626; doi:10.1039/c9cc09178e

data_7125907
_publ_section_title
;
 Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones.
;
_journal_issue                   4
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              623
_journal_page_last               626
_journal_paper_doi               10.1039/c9cc09178e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety
'0.5(C20 H16.55 Cl N O2), 0.5(C20 H18 Cl N O2)'
_chemical_formula_sum            'C20 H17.27 Cl N O2'
_chemical_formula_weight         339.07
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.00050(10)
_cell_length_b                   15.08900(10)
_cell_length_c                   23.6172(2)
_cell_measurement_reflns_used    19779
_cell_measurement_temperature    278(30)
_cell_measurement_theta_max      71.4920
_cell_measurement_theta_min      4.7390
_cell_volume                     3563.78(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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      air
_diffrn_ambient_temperature      278(30)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -53.00  31.00   1.00    1.00    --  -35.97  57.00 -30.00   84
  2  \w   -105.00  33.00   1.00    1.00    --  -35.97   0.00 150.00  138
  3  \w    -53.00  31.00   1.00    1.00    --  -35.97  57.00-180.00   84
  4  \w    -33.00  55.00   1.00    1.00    --   35.97 -38.00  60.00   88
  5  \w     24.00  90.00   1.00    1.00    --   35.97-126.00 120.00   66
  6  \w     24.00  90.00   1.00    1.00    --   35.97-126.00  60.00   66
  7  \w     24.00  90.00   1.00    1.00    --   35.97-126.00 -60.00   66
  8  \w     24.00  90.00   1.00    1.00    --   35.97-126.00-120.00   66
  9  \w     38.00 129.00   1.00    2.15    --  107.97 -30.00 120.00   91
 10  \w     40.00 125.00   1.00    2.15    --  107.97 -45.00  60.00   85
 11  \w     40.00 135.00   1.00    2.15    --  107.97 -77.00 120.00   95
 12  \w     38.00 112.00   1.00    2.15    --  107.97-112.00 120.00   74
 13  \w     39.00 110.00   1.00    2.15    --  107.97 -95.00 -90.00   71
 14  \w     39.00 110.00   1.00    2.15    --  107.97 -95.00-180.00   71
 15  \w     41.00 126.00   1.00    2.15    --  107.97 -61.00-120.00   85
 16  \w     39.00 110.00   1.00    2.15    --  107.97 -95.00  30.00   71
 17  \w     40.00 125.00   1.00    2.15    --  107.97 -45.00-120.00   85
 18  \w     87.00 178.00   1.00    2.15    --  107.97  30.00  60.00   91
 19  \w     40.00 125.00   1.00    2.15    --  107.97 -45.00 -30.00   85
 20  \w     38.00 112.00   1.00    2.15    --  107.97-112.00   0.00   74
 21  \w     39.00 110.00   1.00    2.15    --  107.97 -95.00 150.00   71
 22  \w     39.00 177.00   1.00    2.15    --  107.97   0.00   0.00  138
 23  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  30.00   84
 24  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00 120.00   84
 25  \w     17.00 105.00   1.00    1.00    --   35.97  38.00  60.00   88
 26  \w      9.00 104.00   1.00    1.00    --   35.97  77.00  60.00   95
 27  \w      9.00 104.00   1.00    1.00    --   35.97  77.00-150.00   95
 28  \w      9.00 104.00   1.00    1.00    --   35.97  77.00 -60.00   95
 29  \w     70.00 155.00   1.00    2.15    --  107.97  15.00-180.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1280650000
_diffrn_orient_matrix_UB_12      -0.0565457000
_diffrn_orient_matrix_UB_13      -0.0032411000
_diffrn_orient_matrix_UB_21      0.0856659000
_diffrn_orient_matrix_UB_22      0.0846190000
_diffrn_orient_matrix_UB_23      0.0041750000
_diffrn_orient_matrix_UB_31      0.0008491000
_diffrn_orient_matrix_UB_32      -0.0082340000
_diffrn_orient_matrix_UB_33      0.0649990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40048
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.881
_diffrn_reflns_theta_min         3.476
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       needle
_exptl_crystal_F_000             1418
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         6958
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0550P)^2^+0.4360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6632
_reflns_number_total             6958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09178e2.cif
_cod_data_source_block           gz190604_lfy
_cod_database_code               7125907
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
_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, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C37 \\sim C0AA \\sim C38 \\sim C1AA \\sim C39 \\sim C0 \\sim C36: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
3. Others
 Sof(H36A)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(C0)=
 Sof(H0)=1-FVAR(1)
 Sof(H36)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(C37)=
 Sof(H37A)=Sof(H37B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C35(H35)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C17(H17A,H17B), C39(H39A,H39B), C19(H19A,H19B), C38(H38A,
 H38B), C37(H37A,H37B), C18(H18A,H18B), C0AA(H0AA,H0AB), C1AA(H1AA,H1AB)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C22(H22), C25(H25), C2(H2A), C10(H10), C30(H30), C23(H23),
 C5(H5), C3(H3), C34(H34), C33(H33), C14(H14), C32(H32), C11(H11), C31(H31),
 C12(H12), C13(H13), C0(H0)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2019-06-04
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.631