Construction of polycyclic structures with vicinal all-carbon quaternary stereocenters <i>via</i> an enantioselective photoenolization/Diels-Alder reaction.
Hou, Min; Xu, Mengmeng; Yang, Baochao; He, Haibing; Gao, Shuanhu; Chemical science 12 (2021) 7575–7582; doi:10.1039/d1sc00883h

data_1562173
_publ_section_title
;
 Construction of polycyclic structures with vicinal all-carbon quaternary
 stereocenters <i>via</i> an enantioselective photoenolization/Diels-Alder
 reaction.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              7575
_journal_page_last               7582
_journal_paper_doi               10.1039/d1sc00883h
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H28 O4'
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-15 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.73630(10)
_cell_length_b                   7.52970(10)
_cell_length_c                   13.3695(2)
_cell_measurement_reflns_used    15601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9280
_cell_measurement_theta_min      5.0540
_cell_volume                     879.45(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -88.00 -36.00   1.00    1.00    --    0.00 -57.00-180.00   52
  2  \w    -88.00  18.00   1.00    1.00    --    0.00 -38.00-120.00  106
  3  \w    -83.00 -47.00   1.00    1.00    --    0.00 -19.00 -30.00   36
  4  \w    -22.00  19.00   1.00    1.00    --    0.00 -57.00-180.00   41
  5  \w    -23.00  14.00   1.00    1.00    --    0.00  57.00-120.00   37
  6  \w    -40.00  19.00   1.00    1.00    --    0.00 -19.00 -30.00   59
  7  \w    -17.00  15.00   1.00    1.00    --    0.00  38.00 120.00   32
  8  \w    -45.00 -19.00   1.00    1.00    --    0.00 -38.00  30.00   26
  9  \w    -71.00  -3.00   1.00    1.00    --    0.00 -38.00 -60.00   68
 10  \w    -61.00  19.00   1.00    1.00    --    0.00 -38.00  90.00   80
 11  \w    -18.00  19.00   1.00    1.00    --    0.00 -38.00  30.00   37
 12  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 13  \w    121.00 161.00   1.00    1.00    --   95.80  80.00 104.93   40
 14  \w    121.00 147.00   1.00    1.00    --   95.80  82.00-120.00   26
 15  \w     76.00 133.00   1.00    1.00    --   95.80  61.00  90.00   57
 16  \w     63.00  93.00   1.00    1.00    --   95.80  82.00-150.00   30
 17  \w     64.00  90.00   1.00    1.00    --   95.80  80.00 104.93   26
 18  \w     71.00 121.00   1.00    1.00    --   95.80  66.00 -28.25   50
 19  \w     75.00 128.00   1.00    1.00    --   95.80 -82.00-180.00   53
 20  \w     69.00 105.00   1.00    1.00    --   95.80  68.00  97.47   36
 21  \w      6.00  67.00   1.00    1.00    --   95.80 -82.00-180.00   61
 22  \w    119.00 145.00   1.00    1.00    --   95.80  45.00-180.00   26
 23  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 24  \w     50.00 120.00   1.00    1.00    --   95.80 -82.00 -60.00   70
 25  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-120.00   26
 26  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 27  \w     71.00 182.00   1.00    1.00    --   95.80  61.00  60.00  111
 28  \w     72.00  99.00   1.00    1.00    --   95.80  61.00 -90.00   27
 29  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 120.00   26
 30  \w    116.00 184.00   1.00    1.00    --   95.80  82.00 120.00   68
 31  \w    145.00 185.00   1.00    1.00    --   95.80  80.00 -17.60   40
 32  \w     75.00 185.00   1.00    1.00    --   95.80  55.00-165.24  110
 33  \w     76.00 102.00   1.00    1.00    --   95.80  45.00-180.00   26
 34  \w     64.00  90.00   1.00    1.00    --   95.80  80.00 -17.60   26
 35  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 150.00   27
 36  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 37  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 38  \w      8.00  62.00   1.00    1.00    --   95.80 -61.00  30.00   54
 39  \w     67.00 120.00   1.00    1.00    --   95.80 -61.00  30.00   53
 40  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 41  \w     66.00  92.00   1.00    1.00    --   95.80  82.00  90.00   26
 42  \w    110.00 182.00   1.00    1.00    --   95.80  82.00  90.00   72
 43  \w     75.00 159.00   1.00    1.00    --   95.80  45.00 -90.00   84
 44  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 45  \w     36.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   91
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 47  \w      6.00 126.00   1.00    1.00    --   95.80 -77.00 150.00  120
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 49  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-180.00   26
 50  \w     71.00 185.00   1.00    1.00    --   95.80  61.00   0.00  114
 51  \w     66.00 138.00   1.00    1.00    --   95.80  82.00 -90.00   72
 52  \w     69.00  95.00   1.00    1.00    --   95.80  65.00  68.67   26
 53  \w    123.00 148.00   1.00    1.00    --   95.80  66.00 -28.25   25
 54  \w     75.00 181.00   1.00    1.00    --   95.80  45.00 -30.00  106
 55  \w    155.00 180.00   1.00    1.00    --   95.80  58.00  41.45   25
 56  \w     65.00 115.00   1.00    1.00    --   95.80  77.00 120.00   50
 57  \w     77.00 102.00   1.00    1.00    --   95.80  30.00 -90.00   25
 58  \w     71.00 114.00   1.00    1.00    --   95.80  61.00-150.00   43
 59  \w     72.00  98.00   1.00    1.00    --   95.80  58.00  41.45   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1515152000
_diffrn_orient_matrix_UB_12      0.0017990000
_diffrn_orient_matrix_UB_13      -0.0582962000
_diffrn_orient_matrix_UB_21      -0.0893333000
_diffrn_orient_matrix_UB_22      -0.0238616000
_diffrn_orient_matrix_UB_23      -0.0987334000
_diffrn_orient_matrix_UB_31      -0.0120533000
_diffrn_orient_matrix_UB_32      0.2033197000
_diffrn_orient_matrix_UB_33      -0.0110276000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17821
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         5.063
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0383P)^2^+0.1762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2931
_reflns_number_total             2951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00883h2.cif
_cod_data_source_block           exp_764
_cod_depositor_comments
'Adding full bibliography for 1562171--1562180.cif.'
_cod_database_code               1562173
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.94
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C18(H18)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              84236
_shelx_hkl_checksum              11198
_shelx_fab_checksum              10237
_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 2.118
_oxdiff_exptl_absorpt_empirical_full_min 0.547