Highly Regio-, Diastereo- and Enantioselective Deracemization of Axially Chiral 3-Alkylideneoxindoles
Mei, Hongjiang; Lin, Lili; Wang, Lifeng; Dai, Li; Liu, Xiaohua; Feng, Xiaoming; Chem. Commun.  (2017) –; doi:10.1039/C7CC05164F

data_7120446
_publ_section_title
;
 Highly Regio-, Diastereo- and Enantioselective Deracemization of Axially
 Chiral 3-Alkylideneoxindoles
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC05164F
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H28 Br N O2'
_chemical_formula_sum            'C30 H28 Br N O2'
_chemical_formula_weight         514.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-03-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.778(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4694(6)
_cell_length_b                   29.3171(7)
_cell_length_c                   9.33198(18)
_cell_measurement_reflns_used    7913
_cell_measurement_temperature    293.57(10)
_cell_measurement_theta_max      70.2200
_cell_measurement_theta_min      5.0320
_cell_volume                     5599.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293.57(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   30.0000 84

  2 omega  -31.00   53.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -120.0000 84

  3 omega    1.00   75.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

  4 omega   20.00  104.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -30.0000 84

  5 omega   20.00  104.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

  6 omega   23.00   90.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000 -180.0000 67

  7 omega   23.00   90.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  -60.0000 67

  8 omega  -31.00   53.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  120.0000 84

  9 omega  -31.00   53.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -180.0000 84

 10 omega  -31.00   53.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -60.0000 84

 11 omega   18.00  106.00   1.0000    4.9950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  120.0000 88

 12 omega   40.00   98.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 13 omega   38.00   91.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 14 omega   39.00  109.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 15 omega   40.00   98.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 16 omega   41.00  126.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

 17 omega   39.00  109.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 18 omega   91.00  176.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 19 omega   41.00  126.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 85

 20 omega   39.00  109.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 21 omega   40.00   98.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 22 omega   38.00   91.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 23 omega   38.00  116.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 78

 24 omega   37.00  146.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000    0.0000 109

 25 omega   38.00  113.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -107.0000  107.0000 75

 26 omega   39.00  139.00   1.0000   19.9750
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0202535000
_diffrn_orient_matrix_UB_12      -0.0460211000
_diffrn_orient_matrix_UB_13      -0.0656293000
_diffrn_orient_matrix_UB_21      0.0663388000
_diffrn_orient_matrix_UB_22      0.0205871000
_diffrn_orient_matrix_UB_23      -0.0416493000
_diffrn_orient_matrix_UB_31      0.0292374000
_diffrn_orient_matrix_UB_32      -0.0148167000
_diffrn_orient_matrix_UB_33      0.1456494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            25155
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.320
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.220
_exptl_crystal_description       prism
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 3231 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         9968
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0713
_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^)+(0.1431P)^2^+0.7734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2186
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                8155
_reflns_number_total             9968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05164f2.cif
_cod_data_source_block           fxm-mhj-pbr
_cod_depositor_comments
;

2017-11-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C30 H28 Br N O2)'
_cod_original_formula_sum        'C60 H56 Br2 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1028.88
_cod_database_code               7120446
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C00I(H00I), C00J(H00J), C00T(H00T), C011(H011), C01D(H01G)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00C), C00N(H00D,H00E), C00V(H00F,H00G), C010(H01Q,H01R), C015(H01A,
 H01B), C018(H01C,H01D), C01B(H01E,H01F), C01F(H01X,H01Y)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), N00A(H00A), C00P(H00P), C00U(H00U), C00X(H00X), C00Z(H00Z),
 C013(H013), C014(H014), C016(H016), C017(H017), C019(H019), C01A(H01S),
 C01C(H01T), C01E(H01H), C01G(H01Z), C01H(H01I), C01I(H01J), C01J(H01K),
 C01K(H01), C01L(H0AA), C01M(H01M), C01N(H01N), C01O(H1AA), C01P(H2AA),
 C01S(H4AA), C01U(H01U), C01V(H01V), C01W(H01W)
2.d Idealised Me refined as rotating group:
 C01R(H3AA,H,HA), C01T(H01L,H01O,H01P)
;
_olex2_date_sample_data_collection 2017-02-22
_olex2_submission_special_instructions 'No special instructions were received'