Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles.
Deng, Yu-Hua; Zhang, Xiang-Zhi; Yu, Ke-Yin; Yan, Xu; Du, Ji-Yuan; Huang, Hanmin; Fan, Chun-An; Chemical communications (Cambridge, England) 52 (2016) 4183–4186; doi:10.1039/c5cc10502a

data_7118757
_publ_section_title
;
 Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic
 1,6-conjugate addition/aromatization of para-quinone methides with
 oxindoles.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4183
_journal_page_last               4186
_journal_paper_doi               10.1039/c5cc10502a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C38 H41 N O2'
_chemical_formula_sum            'C38 H41 N O2'
_chemical_formula_weight         543.72
_chemical_melting_point          443
_chemical_name_systematic        'Diarylmethine-substituted Oxindole 3ab'
_chemical_properties_physical    Light-sensitive
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-07-01
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-11 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.295(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5705(3)
_cell_length_b                   20.6075(7)
_cell_length_c                   15.8172(4)
_cell_measurement_reflns_used    12473
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.7180
_cell_measurement_theta_min      4.6040
_cell_volume                     3119.49(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
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_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
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;
  1 omega   24.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 99

  2 omega  119.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  104.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   69.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   53.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 26

  6 omega   44.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 35

  7 omega   35.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 33

  8 omega   46.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 46

  9 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 25

 10 omega   39.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 77

 11 omega   35.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 47

 12 omega   37.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 40

 13 omega   54.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 36

 14 omega    9.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   30.0000 78

 15 omega  -16.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 86

 16 omega   39.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 27

 17 omega    5.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 33

 18 omega  -67.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 39

 19 omega  -18.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 31

 20 omega  -46.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -64.0000  -54.0000 27

 21 omega   39.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 27

 22 omega   44.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -90.0000 36

 23 omega   27.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 47

 24 omega   44.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 36

 25 omega   30.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   90.0000 92

 26 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 26

 27 omega  115.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 30

 28 omega   79.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000    0.0000 96

 29 omega   61.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 43

 30 omega   62.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 51

 31 omega  146.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0570350000
_diffrn_orient_matrix_UB_12      -0.0533891000
_diffrn_orient_matrix_UB_13      0.0586552000
_diffrn_orient_matrix_UB_21      0.1488512000
_diffrn_orient_matrix_UB_22      -0.0127565000
_diffrn_orient_matrix_UB_23      0.0336784000
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_diffrn_orient_matrix_UB_32      0.0508041000
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_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18325
_diffrn_reflns_point_group_measured_fraction_full 0.765
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.862
_diffrn_reflns_theta_min         3.523
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether / dichloromethane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         8860
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0507P)^2^+0.5086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.504
_reflns_Friedel_fraction_full    0.532
_reflns_Friedel_fraction_max     0.518
_reflns_number_gt                8510
_reflns_number_total             8860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10502a2.cif
_cod_data_source_block           dengyh0630_3
_cod_depositor_comments          'Adding full bibliography for 7118757.cif.'
_cod_original_cell_volume        3119.50(17)
_cod_database_code               7118757
_reflns_odcompleteness_completeness 98.38
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C30(H30), C40(H40), C41(H41), C42(H42), C43(H43), C48(H48), C51(H51),
 C52(H52), C53(H53), C54(H54), C55(H55), C58(H58), C59(H59), C60(H60), C61(H61),
  C62(H62), C64(H64), C68(H68)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C49(H49A,H49B)
2.e Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C70(H70A,H70B,H70C), C71(H71A,
 H71B,H71C), C72(H72A,H72B,H72C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C),
 C76(H76A,H76B,H76C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_shelx_res_checksum              46151
_shelx_hkl_checksum              99714
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'