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_7128639
_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         'C41 H31 Br N2 O3'
_chemical_formula_sum            'C41 H31 Br N2 O3'
_chemical_formula_weight         679.59
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-16 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.5300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.02430(10)
_cell_length_b                   11.28740(10)
_cell_length_c                   19.8460(2)
_cell_measurement_reflns_used    26591
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.6800
_cell_measurement_theta_min      2.2210
_cell_volume                     3813.45(6)
_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      99.99(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 0.982
_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     32.00 119.00   0.50    0.05    --   46.37  43.00 -41.00  174
  2  \w     30.00 118.00   0.50    0.05    --   46.37  57.00  30.00  176
  3  \w     30.00 118.00   0.50    0.05    --   46.37  57.00  90.00  176
  4  \w     32.00 120.00   0.50    0.05    --   46.37  38.00 120.00  176
  5  \w     94.00 138.00   0.50    0.50    --  107.00  77.00  90.00   88
  6  \w     92.00 178.00   0.50    0.50    --  107.00  43.00 -41.00  172
  7  \w     95.00 166.00   0.50    0.50    --  107.00  30.00 -90.00  142
  8  \w    126.00 177.00   0.50    0.50    --  107.00  61.00-150.00  102
  9  \w    140.00 167.00   0.50    0.50    --  107.00  15.00-180.00   54
 10  \w     34.00  73.00   0.50    0.50    --  107.00 -61.00  30.00   78
 11  \w     34.00 105.00   0.50    0.50    --  107.00 -77.00 150.00  142
 12  \w     35.00  60.00   0.50    0.50    --  107.00 -61.00 120.00   50
 13  \w     39.00  65.00   0.50    0.50    --  107.00 -77.00 -30.00   52
 14  \w     70.00 106.00   0.50    0.50    --  107.00 -77.00 -30.00   72
 15  \w     35.00  73.00   0.50    0.50    --  107.00 -61.00-150.00   76
 16  \w     35.00  73.00   0.50    0.50    --  107.00 -61.00-180.00   76
 17  \w     37.00 109.00   0.50    0.50    --  107.00-113.00   0.96  144
 18  \w    -62.00  27.00   0.50    0.05    --  -46.37  57.00-180.00  178
 19  \w    -46.00  27.00   0.50    0.05    --  -46.37  43.00 -41.00  146
 20  \w    -26.00  50.00   0.50    0.05    --   46.37 -43.00 167.00  152
 21  \w     84.00 142.00   0.50    0.50    --  107.00 125.00 150.00  116
 22  \w    -29.00  28.00   0.50    0.05    --   46.37 -19.00  30.00  114
 23  \w   -119.00 -32.00   0.50    0.05    --  -46.37 -43.00 167.00  174
 24  \w   -169.00-122.00   0.50    0.50    -- -100.00 -77.00 120.00   94
 25  \w   -146.00-120.00   0.50    0.50    -- -100.00 -77.00  90.00   52
 26  \w   -173.00 -76.00   0.50    0.50    -- -100.00 -77.00  60.00  194
 27  \w   -101.00 -76.00   0.50    0.50    -- -100.00 -77.00  90.00   50
 28  \w   -102.00 -76.00   0.50    0.50    -- -100.00 -77.00 120.00   52
 29  \w   -114.00 -76.00   0.50    0.50    -- -100.00 -76.00 129.11   76
 30  \w   -168.00-133.00   0.50    0.50    -- -100.00 -76.00 129.11   70
 31  \w   -166.00-138.00   0.50    0.50    -- -100.00 -73.00  78.70   56
 32  \w   -109.00 -77.00   0.50    0.50    -- -100.00 -75.00  23.25   64
 33  \w   -106.00 -80.00   0.50    0.50    -- -100.00 -71.00  29.78   52
 34  \w   -172.00-143.00   0.50    0.50    -- -100.00 -75.00  23.25   58
 35  \w   -167.00-141.00   0.50    0.50    -- -100.00 -71.00  29.78   52
 36  \w   -171.00-130.00   0.50    0.50    -- -100.00 -65.00  97.63   82
 37  \w   -118.00 -80.00   0.50    0.50    -- -100.00 -73.00  78.70   76
 38  \w   -107.00 -81.00   0.50    0.50    -- -100.00 -65.00  97.63   52
 39  \w   -108.00 -82.00   0.50    0.50    -- -100.00 -63.00  52.57   52
 40  \w   -107.00 -82.00   0.50    0.50    -- -100.00 -62.00  49.82   50
 41  \w   -173.00 -82.00   0.50    0.50    -- -100.00 -61.00  60.00  182
 42  \w   -159.00 -81.00   0.50    0.50    -- -100.00 -65.00  36.66  156
 43  \w   -173.00 -81.00   0.50    0.50    -- -100.00 -64.00  -3.02  184
 44  \w   -170.00-129.00   0.50    0.50    -- -100.00 -51.00 -51.84   82
 45  \w   -109.00 -84.00   0.50    0.50    -- -100.00 -51.00 -51.84   50
 46  \w   -120.00 -92.00   0.50    0.50    -- -100.00 -49.00 -83.14   56
 47  \w   -172.00-128.00   0.50    0.50    -- -100.00 -49.00 -83.14   88
 48  \w   -126.00 -85.00   0.50    0.50    -- -100.00 -45.00  60.00   82
 49  \w   -161.00 -83.00   0.50    0.50    -- -100.00 -60.00  22.94  156
 50  \w   -172.00 -84.00   0.50    0.50    -- -100.00 -46.00  33.02  176
 51  \w   -113.00 -86.00   0.50    0.50    -- -100.00 -56.00  91.84   54
 52  \w   -167.00 -91.00   0.50    0.50    -- -100.00 -55.00 128.59  152
 53  \w   -174.00 -85.00   0.50    0.50    -- -100.00 -43.00 167.00  178
 54  \w    -99.00 -73.00   0.50    0.50    -- -100.00  77.00  60.00   52
 55  \w    -69.00 -44.00   0.50    0.50    -- -100.00  61.00  60.00   50
 56  \w    -54.00 -28.00   0.50    0.50    -- -100.00  77.00  60.00   52
 57  \w    -69.00 -44.00   0.50    0.50    -- -100.00  61.00  90.00   50
 58  \w    -62.00 -32.00   0.50    0.50    -- -100.00  61.00 150.00   60
;
_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      -0.0005194000
_diffrn_orient_matrix_UB_12      -0.0337110000
_diffrn_orient_matrix_UB_13      -0.0751894000
_diffrn_orient_matrix_UB_21      0.0783736000
_diffrn_orient_matrix_UB_22      -0.0663055000
_diffrn_orient_matrix_UB_23      0.0098416000
_diffrn_orient_matrix_UB_31      -0.0453208000
_diffrn_orient_matrix_UB_32      -0.1144417000
_diffrn_orient_matrix_UB_33      0.0164402000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38776
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.796
_diffrn_reflns_theta_min         2.226
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79701
_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    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 3370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7732
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0813P)^2^+10.3921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                7535
_reflns_number_total             7732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02876f2.cif
_cod_data_source_block           yuanhx_201231
_cod_depositor_comments
'Adding full bibliography for 7128639--7128640.cif.'
_cod_database_code               7128639
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C00D(H00D), C00G(H00G), C00K(H00K), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C017(H017), C018(H018),
 C01A(H01A), C01B(H01B), C01D(H01D), C01E(H01E)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4187
_shelx_fab_checksum              50765
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.731