Enantioselective assembly of 3,3-disubstituted succinimides <i>via</i> three-component reaction of vinyl diazosuccinimides with alcohols and imines.
Yuan, Haoxuan; Hong, Kemiao; Liu, Xiangrong; Qian, Yu; Xu, Xinfang; Hu, Wenhao; Chemical communications (Cambridge, England) 57 (2021) 8043–8046; doi:10.1039/d1cc02876f

data_7128640
_publ_section_title
;
 Enantioselective assembly of 3,3-disubstituted succinimides <i>via</i>
 three-component reaction of vinyl diazosuccinimides with alcohols and
 imines.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8043
_journal_page_last               8046
_journal_paper_doi               10.1039/d1cc02876f
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H27 Br3 N2 O3'
_chemical_formula_sum            'C37 H27 Br3 N2 O3'
_chemical_formula_weight         787.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-16 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.42920(10)
_cell_length_b                   17.26420(10)
_cell_length_c                   22.5485(2)
_cell_measurement_reflns_used    18860
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6390
_cell_measurement_theta_min      3.2150
_cell_volume                     3281.33(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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     82.00 128.00   0.50    0.05    --  107.00 124.00  42.00   92
  2  \w    130.00 156.00   0.50    0.05    --  107.00 124.00  42.00   52
  3  \w    115.00 159.00   0.50    0.05    --  107.00  33.00 -18.00   88
  4  \w    -19.00  40.00   0.50    0.05    --   46.62 -33.00-177.00  118
  5  \w     37.00  71.00   0.50    0.05    --  107.00 -61.00 -90.00   68
  6  \w     34.00  59.00   0.50    0.05    --  107.00 -61.00 -60.00   50
  7  \w    -29.00  27.00   0.50    0.05    --   46.62 -19.00  60.00  112
  8  \w     34.00  59.00   0.50    0.05    --  107.00 -61.00  60.00   50
  9  \w    -78.00 -29.00   0.50    0.05    -- -100.00  90.00 151.00   98
 10  \w    -95.00 -41.00   0.50    0.05    -- -100.00  77.00 150.00  108
 11  \w   -102.00 -36.00   0.50    0.05    -- -100.00  77.00 120.00  132
 12  \w   -102.00 -33.00   0.50    0.05    -- -100.00  77.00-120.00  138
 13  \w    -18.00  29.00   0.50    0.05    --  -46.62  19.00  60.00   94
 14  \w   -119.00 -83.00   0.50    0.05    --  -46.62-125.00   0.00   72
 15  \w     59.00 108.00   0.50    0.05    --   46.37  33.00 -18.00   98
 16  \w     -5.00  22.00   0.50    0.05    --  -46.37  19.00 -30.00   54
 17  \w    -69.00 -44.00   0.50    0.05    -- -100.00  61.00 120.00   50
 18  \w     34.00  73.00   0.50    0.05    --  107.00 -61.00  90.00   78
 19  \w     43.00  90.00   0.50    0.05    --  107.00 -90.00  37.00   94
 20  \w     38.00  95.00   0.50    0.05    --  107.00 -77.00-120.00  114
 21  \w     38.00  65.00   0.50    0.05    --  107.00-125.00-150.00   54
 22  \w    128.00 164.00   0.50    0.05    --  107.00  77.00 120.00   72
 23  \w     83.00 118.00   0.50    0.05    --  107.00  77.00 120.00   70
 24  \w     48.00  79.00   0.50    0.05    --  107.00 -94.00  90.00   62
 25  \w    142.00 170.00   0.50    0.05    --  107.00  30.00  30.00   56
 26  \w     69.00 106.00   0.50    0.05    --  107.00 -77.00 -90.00   74
 27  \w     37.00  94.00   0.50    0.05    --  107.00 -77.00-180.00  114
 28  \w    140.00 176.00   0.50    0.05    --  107.00  45.00-150.00   72
 29  \w     85.00 111.00   0.50    0.05    --  107.00-125.00-150.00   52
 30  \w     93.00 131.00   0.50    0.05    --  107.00  45.00-150.00   76
 31  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00-120.00  190
 32  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00  30.00  190
 33  \w   -118.00 -56.00   0.50    0.05    --  -46.37 -57.00 -60.00  124
 34  \w   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00 120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1819416000
_diffrn_orient_matrix_UB_12      0.0066337000
_diffrn_orient_matrix_UB_13      0.0039596000
_diffrn_orient_matrix_UB_21      -0.0079334000
_diffrn_orient_matrix_UB_22      -0.0810189000
_diffrn_orient_matrix_UB_23      0.0285061000
_diffrn_orient_matrix_UB_31      0.0152607000
_diffrn_orient_matrix_UB_32      0.0368292000
_diffrn_orient_matrix_UB_33      0.0619616000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.960
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 2567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                6367
_reflns_number_total             6776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02876f2.cif
_cod_data_source_block           yuanhx_210225
_cod_depositor_comments
'Adding full bibliography for 7128639--7128640.cif.'
_cod_database_code               7128640
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.641
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C24(H24), C6(H6), C26(H26), C25(H25), C3(H3), C14(H14), C23(H23),
 C22(H22), C13(H13), C27(H27), C41(H41), C29(H29), C31(H31), C5(H5), C12(H12),
 C11(H11), C32(H32), C30(H30), C33(H33), C37(H37), C39(H39), C40(H40), C38(H38)
;
_shelx_res_checksum              78103
_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 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.739