Catalytic asymmetric coupling of vinylogous species <i>via</i> deconjugated butenolide addition to vinylogous imines <i>in situ</i> generated from arylsulfonyl indoles.
Yuan, Shu-Pei; Zhang, Xia-Yan; Jia, Yun-Qing; Wang, Zhen-Hua; Zhao, Jian-Qiang; You, Yong; Zhou, Ming-Qiang; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 57 (2021) 4938–4941; doi:10.1039/d1cc00777g

data_7128171
_publ_section_title
;
 Catalytic asymmetric coupling of vinylogous species <i>via</i>
 deconjugated butenolide addition to vinylogous imines <i>in situ</i>
 generated from arylsulfonyl indoles.
;
_journal_issue                   40
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4938
_journal_page_last               4941
_journal_paper_doi               10.1039/d1cc00777g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-01 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                93.016(7)
_cell_angle_beta                 99.314(7)
_cell_angle_gamma                116.142(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2533(10)
_cell_length_b                   10.7469(10)
_cell_length_c                   11.7360(9)
_cell_measurement_reflns_used    1324
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3740
_cell_measurement_theta_min      3.8310
_cell_volume                     1134.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -102.00 -15.00   1.00    1.50    --  -33.50 -57.00 -60.00   87
  2  \w   -108.00 -32.00   1.00    1.50    --  -33.50 178.00  90.00   76
  3  \w   -108.00 -32.00   1.00    1.50    --  -33.50 178.00 -30.00   76
  4  \w    -71.00  39.00   1.00    1.50    --  -33.50  19.00 120.00  110
  5  \w     59.00  97.00   1.00    1.50    --   36.47 178.00 -30.00   38
  6  \w     27.00  54.00   1.00    1.50    --   36.47  77.00   0.00   27
  7  \w     -3.00  25.00   1.00    1.50    --   36.47 -99.00   0.00   28
  8  \w     27.00  75.00   1.00    1.50    --   36.47 -99.00   0.00   48
  9  \w     41.00  74.00   1.00    1.50    --   36.47 -99.00-180.00   33
 10  \w     52.00 104.00   1.00    1.50    --   36.47  19.00 150.00   52
 11  \w     32.00  70.00   1.00    1.50    --   36.47  37.00-150.00   38
 12  \w     74.00 105.00   1.00    1.50    --   36.47  77.00   0.00   31
 13  \w     36.00  75.00   1.00    1.50    --   36.47 -99.00 -90.00   39
 14  \w      0.00  44.00   1.00    1.50    --   36.47  19.00 150.00   44
 15  \w     -3.00  30.00   1.00    1.50    --   36.47 -99.00 -90.00   33
 16  \w     66.00  91.00   1.00    1.50    --   36.47 178.00  60.00   25
 17  \w     67.00 108.00   1.00    1.50    --   36.47 178.00-150.00   41
 18  \w     70.00 112.00   1.00    7.00    --  108.00-111.00 -90.00   42
 19  \w    126.00 173.00   1.00    7.00    --  108.00 111.00 120.00   47
 20  \w     53.00 134.00   1.00    7.00    --  108.00 -77.00  90.00   81
 21  \w     85.00 110.00   1.00    7.00    --  108.00-111.00 120.00   25
 22  \w    115.00 147.00   1.00    7.00    --  108.00 178.00 120.00   32
 23  \w     43.00 125.00   1.00    7.00    --  108.00 -61.00-150.00   82
 24  \w     39.00  65.00   1.00    7.00    --  108.00-111.00 120.00   26
 25  \w     80.00 112.00   1.00    7.00    --  108.00 178.00 120.00   32
 26  \w    125.00 176.00   1.00    7.00    --  108.00  61.00-180.00   51
 27  \w     51.00 149.00   1.00    7.00    --  108.00 -15.00-150.00   98
 28  \w     70.00 122.00   1.00    7.00    --  108.00 -30.00 150.00   52
 29  \w     38.00  64.00   1.00    7.00    --  108.00 -30.00 150.00   26
 30  \w     46.00  91.00   1.00    7.00    --  108.00 -94.00-180.00   45
 31  \w     88.00 175.00   1.00    7.00    --  108.00  45.00-120.00   87
 32  \w     38.00 126.00   1.00    7.00    --  108.00 -30.00  60.00   88
 33  \w    114.00 169.00   1.00    7.00    --  108.00 131.00-174.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1133619000
_diffrn_orient_matrix_UB_12      -0.0535379000
_diffrn_orient_matrix_UB_13      -0.1168162000
_diffrn_orient_matrix_UB_21      -0.1277820000
_diffrn_orient_matrix_UB_22      -0.0405771000
_diffrn_orient_matrix_UB_23      0.0662547000
_diffrn_orient_matrix_UB_31      0.0089931000
_diffrn_orient_matrix_UB_32      0.1466108000
_diffrn_orient_matrix_UB_33      -0.0036513000
_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     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         3.855
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0554P)^2^+0.0907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2581
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00777g2.cif
_cod_data_source_block           202010214
_cod_depositor_comments
'Adding full bibliography for 7128170--7128171.cif.'
_cod_original_cell_volume        1134.4(2)
_cod_database_code               7128171
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C27(H27A,H27B,H27C)
;
_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.878