Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes.
Jiang, Bo; Du, Wei; Chen, Ying-Chun; Chemical communications (Cambridge, England) 56 (2020) 7257–7260; doi:10.1039/d0cc02836c

data_7126587
_publ_section_title
;
 Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations
 of cyclobutenones and 1-azadienes.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7257
_journal_page_last               7260
_journal_paper_doi               10.1039/d0cc02836c
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H27 N O4 S'
_chemical_formula_sum            'C33 H27 N O4 S'
_chemical_formula_weight         533.61
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-19 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   27.6807(5)
_cell_length_b                   27.6807(5)
_cell_length_c                   9.6164(3)
_cell_measurement_reflns_used    7132
_cell_measurement_temperature    293.3(7)
_cell_measurement_theta_max      71.6710
_cell_measurement_theta_min      5.9010
_cell_volume                     6381.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.3(7)
_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 0.990
_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    -53.00  31.00   1.00    2.79    --  -36.04  57.00  90.00   84
  2  \w   -103.00 -19.00   1.00    2.79    --  -36.04 -57.00 -60.00   84
  3  \w      9.00 104.00   1.00    2.79    --   36.04  77.00 -30.00   95
  4  \w     36.00  97.00   1.00    2.79    --   36.04  38.00-150.00   61
  5  \w     20.00  45.00   1.00    2.79    --   36.04  57.00-120.00   25
  6  \w     23.00  49.00   1.00    2.79    --   36.04  38.00 -90.00   26
  7  \w     21.00  47.00   1.00    2.79    --   36.04  57.00 150.00   26
  8  \w     25.00  54.00   1.00    2.79    --   36.04  57.00-180.00   29
  9  \w     18.00  48.00   1.00    2.79    --   36.04  77.00 -90.00   30
 10  \w      2.00  75.00   1.00    2.79    --   36.04 -99.00 150.00   73
 11  \w    132.00 165.00   1.00   11.17    --  106.21  77.00-150.00   33
 12  \w     79.00 105.00   1.00   11.17    --  106.21  77.00-120.00   26
 13  \w     79.00 105.00   1.00   11.17    --  106.21  77.00 -90.00   26
 14  \w     79.00 105.00   1.00   11.17    --  106.21  77.00-150.00   26
 15  \w     90.00 115.00   1.00   11.17    --  106.21  61.00-150.00   25
 16  \w     88.00 114.00   1.00   11.17    --  106.21  61.00 -60.00   26
 17  \w    150.00 176.00   1.00   11.17    --  106.21  15.00 -90.00   26
 18  \w     88.00 114.00   1.00   11.17    --  106.21  61.00-120.00   26
 19  \w     91.00 118.00   1.00   11.17    --  106.21  61.00 -90.00   27
 20  \w     85.00 113.00   1.00   11.17    --  106.21-111.00-180.00   28
 21  \w     71.00  97.00   1.00   11.17    --  106.21  15.00 -60.00   26
 22  \w    120.00 173.00   1.00   11.17    --  106.21  77.00 -60.00   53
 23  \w     71.00  97.00   1.00   11.17    --  106.21  15.00 -30.00   26
 24  \w     87.00 113.00   1.00   11.17    --  106.21  30.00 -90.00   26
 25  \w     38.00  63.00   1.00   11.17    --  106.21-111.00-180.00   25
 26  \w     88.00 114.00   1.00   11.17    --  106.21  61.00 150.00   26
 27  \w     88.00 145.00   1.00   11.17    --  106.21  61.00-180.00   57
 28  \w     87.00 122.00   1.00   11.17    --  106.21  30.00 -30.00   35
 29  \w     89.00 115.00   1.00   11.17    --  106.21  61.00 -30.00   26
 30  \w     79.00 104.00   1.00   11.17    --  106.21  77.00 -60.00   25
 31  \w    137.00 164.00   1.00   11.17    --  106.21  77.00 -90.00   27
 32  \w    112.00 174.00   1.00   11.17    --  106.21  77.00-120.00   62
 33  \w     91.00 117.00   1.00   11.17    --  106.21  30.00-120.00   26
 34  \w     89.00 115.00   1.00   11.17    --  106.21  30.00 -60.00   26
 35  \w     81.00 108.00   1.00   11.17    --  106.21  77.00 -30.00   27
 36  \w     69.00  94.00   1.00   11.17    --  106.21  15.00 -90.00   25
 37  \w     40.00 120.00   1.00   11.17    --  106.21 -77.00  60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0262665000
_diffrn_orient_matrix_UB_12      -0.0639296000
_diffrn_orient_matrix_UB_13      -0.0001838000
_diffrn_orient_matrix_UB_21      -0.0585924000
_diffrn_orient_matrix_UB_22      -0.0065406000
_diffrn_orient_matrix_UB_23      0.0067697000
_diffrn_orient_matrix_UB_31      -0.0024258000
_diffrn_orient_matrix_UB_32      -0.0001832000
_diffrn_orient_matrix_UB_33      -0.1600352000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13695
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.683
_diffrn_reflns_theta_min         4.955
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.250
_exptl_crystal_description       needle
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1858 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0507
_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^)+(0.1040P)^2^+1.3196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.764
_reflns_Friedel_fraction_max     0.741
_reflns_number_gt                4569
_reflns_number_total             4776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02836c2.cif
_cod_data_source_block           3y
_cod_depositor_comments          'Adding full bibliography for 7126587.cif.'
_cod_original_cell_volume        6381.2(3)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               7126587
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.88
_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
2.a Ternary CH refined with riding coordinates:
 C00J(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G), C00K(H00K), C00M(H00M),
 C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012), C013(H013)
2.d Idealised Me refined as rotating group:
 C00T(H00D,H00H,H00I), C011(H01A,H01B,H01C)
;
_shelx_res_checksum              19977
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.783
_oxdiff_exptl_absorpt_empirical_full_min 0.663