Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality
Jianlin Zhang; Yulong Zhang; Lili Lin; Qian Yao; Xiaohua Liu; Xiaoming Feng; Chem.Commun. 51 (2015) 10554–; doi:10.1039/C5cc03203B

data_7117317
_publ_section_title
;
 Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient
 construction of both atom chirality and axial chirality
;
_journal_name_full               Chem.Commun.
_journal_page_first              10554
_journal_paper_doi               10.1039/C5cc03203B
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H30 N2 O4'
_chemical_formula_sum            'C30 H30 N2 O4'
_chemical_formula_weight         482.56
_space_group_crystal_system      tetragonal
_space_group_IT_number           80
_space_group_name_Hall           'I 4bw'
_space_group_name_H-M_alt        'I 41'
_symmetry_space_group_name_Hall  'I 4bw'
_symmetry_space_group_name_H-M   'I 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-26
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;
_audit_update_record
;
2014-12-03 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4485(2)
_cell_length_b                   17.4485(2)
_cell_length_c                   16.7110(3)
_cell_measurement_reflns_used    6304
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.4450
_cell_measurement_theta_min      5.0320
_cell_volume                     5087.67(12)
_computing_cell_refinement
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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_data_collection
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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_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)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000  -60.0000 84

  2 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000   30.0000 88

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  -90.0000 74

  4 omega   -8.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -91.0000   26.0000 79

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000   30.0000 67

  6 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -120.0000 84

  7 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000   90.0000 67

  8 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   19.0000 -150.0000 101

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -150.0000 67

 10 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000  150.0000 67

 11 omega   81.00  176.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 12 omega   39.00  109.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 13 omega   40.00   98.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 14 omega   38.00   91.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 15 omega   91.00  176.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

 16 omega   38.00  116.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 17 omega   39.00   64.00   1.0000    3.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 25
;
_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      -0.0784534000
_diffrn_orient_matrix_UB_12      -0.0102134000
_diffrn_orient_matrix_UB_13      -0.0408562000
_diffrn_orient_matrix_UB_21      -0.0079173000
_diffrn_orient_matrix_UB_22      -0.0800265000
_diffrn_orient_matrix_UB_23      0.0382114000
_diffrn_orient_matrix_UB_31      -0.0397190000
_diffrn_orient_matrix_UB_32      0.0359887000
_diffrn_orient_matrix_UB_33      0.0732186000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13326
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         5.070
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54114
_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
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_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0544
_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^)+(0.1048P)^2^+2.8745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.768
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                3878
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03203b2.cif
_cod_data_source_block           fxm-2jl1-100
_cod_original_cell_volume        5087.68(15)
_cod_database_code               7117317
_reflns_odcompleteness_completeness 99.79
_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:
 C00K(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00P(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00C(H00C), C00D(H00D), C00G(H00G), C00I(H00I), C00J(H00J),
 C00L(H00L), C00N(H00N), C00R(H00R), C00S(H00S), C00V(H00V), C00X(H00X),
 C00Y(H00Y)
2.d Idealised Me refined as rotating group:
 C00T(H00H,H00M,H00O), C00U(H00P,H00Q,H00T), C00Z(H00U,H00W,H00Z), C010(H01A,
 H01B,H01C)
;
_shelx_res_checksum              92188
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'