Phosphine-Catalysed Asymmetric Dearomative Formal [4 + 2] Cycloadditions of 3-Benzofuranyl Vinyl Ketones
Xiao, Ben-Xian; Jiang, Bo; Song, Xue; Du, Wei; Chen, Ying-Chun; Chemical Communications  (2019) –; doi:10.1039/C9CC00386J

data_7123001
_publ_section_title
;
 Phosphine-Catalysed Asymmetric Dearomative Formal [4 + 2] Cycloadditions
 of 3-Benzofuranyl Vinyl Ketones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00386J
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H23 F N2 O5'
_chemical_formula_sum            'C25 H23 F N2 O5'
_chemical_formula_weight         450.45
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2019-01-16 deposited with the CCDC.    2019-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2786(4)
_cell_length_b                   18.2786(4)
_cell_length_c                   13.4615(4)
_cell_measurement_reflns_used    6617
_cell_measurement_temperature    295.4(8)
_cell_measurement_theta_max      72.0620
_cell_measurement_theta_min      4.0510
_cell_volume                     4497.58(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      295.4(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_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    -65.00  29.00   1.00    3.10    --  -36.42  19.00-150.00   94
  2  \w    -55.00 -29.00   1.00    3.10    --  -36.42  77.00-180.00   26
  3  \w     22.00  48.00   1.00    3.10    --   36.42  38.00 150.00   26
  4  \w     40.00  66.00   1.00    3.10    --   36.42  19.00-120.00   26
  5  \w     10.00  62.00   1.00    3.10    --   36.42  77.00-150.00   52
  6  \w     10.00  39.00   1.00    3.10    --   36.42  77.00  90.00   29
  7  \w     76.00 101.00   1.00    3.10    --   36.42  38.00 150.00   25
  8  \w     44.00  70.00   1.00    3.10    --   36.42  19.00-150.00   26
  9  \w     36.00  88.00   1.00    3.10    --   36.42-128.00 138.00   52
 10  \w     31.00  63.00   1.00    3.10    --   36.42  57.00 150.00   32
 11  \w     29.00  54.00   1.00    3.10    --   36.42  38.00   0.00   25
 12  \w     10.00  40.00   1.00    3.10    --   36.42  19.00-150.00   30
 13  \w     20.00  64.00   1.00    3.10    --   36.42  57.00 120.00   44
 14  \w    150.00 175.00   1.00   12.41    --  108.71  77.00  90.00   25
 15  \w     91.00 117.00   1.00   12.41    --  108.71  45.00  90.00   26
 16  \w     82.00 108.00   1.00   12.41    --  108.71  77.00  90.00   26
 17  \w     87.00 113.00   1.00   12.41    --  108.71  30.00 150.00   26
 18  \w     92.00 117.00   1.00   12.41    --  108.71  61.00  60.00   25
 19  \w    131.00 157.00   1.00   12.41    --  108.71  77.00 150.00   26
 20  \w    100.00 171.00   1.00   12.41    --  108.71 111.00-150.00   71
 21  \w    151.00 176.00   1.00   12.41    --  108.71  77.00-180.00   25
 22  \w     82.00 108.00   1.00   12.41    --  108.71  77.00 150.00   26
 23  \w     83.00 110.00   1.00   12.41    --  108.71  77.00-180.00   27
 24  \w     96.00 122.00   1.00   12.41    --  108.71  45.00 150.00   26
 25  \w     82.00 108.00   1.00   12.41    --  108.71  77.00  30.00   26
 26  \w     75.00 111.00   1.00   12.41    --  108.71-111.00-180.00   36
 27  \w     82.00 108.00   1.00   12.41    --  108.71  77.00  60.00   26
 28  \w     87.00 113.00   1.00   12.41    --  108.71  30.00-180.00   26
 29  \w     39.00  87.00   1.00   12.41    --  108.71-111.00 -30.00   48
 30  \w     91.00 117.00   1.00   12.41    --  108.71  61.00 120.00   26
 31  \w     91.00 117.00   1.00   12.41    --  108.71  61.00  90.00   26
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0839907000
_diffrn_orient_matrix_UB_12      -0.0057607000
_diffrn_orient_matrix_UB_13      -0.0056268000
_diffrn_orient_matrix_UB_21      0.0054845000
_diffrn_orient_matrix_UB_22      -0.0838678000
_diffrn_orient_matrix_UB_23      0.0082191000
_diffrn_orient_matrix_UB_31      -0.0044816000
_diffrn_orient_matrix_UB_32      0.0057438000
_diffrn_orient_matrix_UB_33      0.1140270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21241
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.070
_diffrn_reflns_theta_min         3.419
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.330
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0515
_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^)+(0.1030P)^2^+0.1432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1457
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3936
_reflns_number_total             4402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00386j2.cif
_cod_data_source_block           3s
_cod_original_cell_volume        4497.6(2)
_cod_database_code               7123001
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.49
_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:
 C00F(H00F), C00I(H00I), C00J(H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00O(H00O), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C), C00R(H00G,H00H,H00K), C00U(H00M,H00N,H00P), C00X(H00Q,
 H00R,H00U)
;
_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 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.648