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_1562176
_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_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
_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             2019-03-04
_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                 107.6040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.09720(10)
_cell_length_b                   7.08550(10)
_cell_length_c                   13.1638(2)
_cell_measurement_reflns_used    13242
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0320
_cell_measurement_theta_min      5.7170
_cell_volume                     719.875(18)
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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 -35.00   1.00    1.00    --    0.00 -38.00 -90.00   53
  2  \w     17.00  43.00   1.00    1.00    --    0.00  57.00   0.00   26
  3  \w    -14.00  21.00   1.00    1.00    --    0.00 -57.00 120.00   35
  4  \w    -88.00 -46.00   1.00    1.00    --    0.00 -57.00   0.00   42
  5  \w    -78.00 -53.00   1.00    1.00    --    0.00 -57.00 120.00   25
  6  \w     20.00  52.00   1.00    1.00    --    0.00  82.00 120.00   32
  7  \w    -30.00   5.00   1.00    1.00    --    0.00  82.00 120.00   35
  8  \w    -83.00 -32.00   1.00    1.00    --    0.00 -19.00  60.00   51
  9  \w    -24.00  22.00   1.00    1.00    --    0.00 -57.00   0.00   46
 10  \w     50.00  89.00   1.00    1.00    --    0.00  57.00   0.00   39
 11  \w    -10.00  19.00   1.00    1.00    --    0.00 -38.00 -90.00   29
 12  \w     38.00  82.00   1.00    1.00    --    0.00  82.00-180.00   44
 13  \w    -29.00  21.00   1.00    1.00    --    0.00 -19.00  60.00   50
 14  \w    -31.00  18.00   1.00    1.00    --    0.00  82.00-180.00   49
 15  \w     71.00 106.00   1.00    1.00    --   95.80  61.00-180.00   35
 16  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00-120.00  122
 17  \w     71.00 105.00   1.00    1.00    --   95.80  60.00 -44.34   34
 18  \w     47.00 120.00   1.00    1.00    --   95.80 -82.00  60.00   73
 19  \w     10.00  36.00   1.00    1.00    --   95.80 -82.00  60.00   26
 20  \w     66.00  91.00   1.00    1.00    --   95.80  75.00 109.73   25
 21  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  93.16   26
 22  \w     63.00  94.00   1.00    1.00    --   95.80  82.00 -60.00   31
 23  \w    129.00 184.00   1.00    1.00    --   95.80  82.00 -60.00   55
 24  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  60.00   26
 25  \w     61.00 110.00   1.00    1.00    --   95.80 -82.00-180.00   49
 26  \w     77.00 120.00   1.00    1.00    --   95.80  30.00  60.00   43
 27  \w     65.00  92.00   1.00    1.00    --   95.80  82.00 -90.00   27
 28  \w    104.00 142.00   1.00    1.00    --   95.80  82.00 -90.00   38
 29  \w     76.00 115.00   1.00    1.00    --   95.80  45.00  60.00   39
 30  \w     76.00 102.00   1.00    1.00    --   95.80  45.00-120.00   26
 31  \w     59.00 125.00   1.00    1.00    --   95.80 -77.00   0.00   66
 32  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-180.00   26
 33  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  60.00   26
 34  \w    143.00 184.00   1.00    1.00    --   95.80  61.00 -90.00   41
 35  \w     68.00  93.00   1.00    1.00    --   95.80  68.00  98.77   25
 36  \w     73.00 138.00   1.00    1.00    --   95.80  61.00 -90.00   65
 37  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 38  \w    125.00 184.00   1.00    1.00    --   95.80  82.00 -30.00   59
 39  \w     71.00 145.00   1.00    1.00    --   95.80  61.00 150.00   74
 40  \w     72.00 184.00   1.00    1.00    --   95.80  61.00-120.00  112
 41  \w     65.00 100.00   1.00    1.00    --   95.80  77.00-180.00   35
 42  \w    150.00 175.00   1.00    1.00    --   95.80  77.00-180.00   25
 43  \w     63.00  98.00   1.00    1.00    --   95.80  82.00 -30.00   35
 44  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 45  \w    160.00 185.00   1.00    1.00    --   95.80  77.00-150.00   25
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 47  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 48  \w     65.00 124.00   1.00    1.00    --   95.80  77.00   0.00   59
 49  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 50  \w    127.00 178.00   1.00    1.00    --   95.80  77.00  60.00   51
 51  \w    119.00 144.00   1.00    1.00    --   95.80  45.00-120.00   25
 52  \w    132.00 184.00   1.00    1.00    --   95.80  61.00-180.00   52
 53  \w    153.00 178.00   1.00    1.00    --   95.80  60.00 -44.34   25
 54  \w     79.00 125.00   1.00    1.00    --   95.80  45.00 120.00   46
 55  \w     71.00 184.00   1.00    1.00    --   95.80  61.00 120.00  113
 56  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 57  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 58  \w     76.00 130.00   1.00    1.00    --   95.80  30.00-150.00   54
 59  \w     82.00 118.00   1.00    1.00    --   95.80  30.00   0.00   36
 60  \w    155.00 181.00   1.00    1.00    --   95.80  77.00  93.16   26
 61  \w    125.00 173.00   1.00    1.00    --   95.80  45.00  95.18   48
 62  \w      6.00 116.00   1.00    1.00    --   95.80 -61.00-120.00  110
 63  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 150.00   26
 64  \w    142.00 176.00   1.00    1.00    --   95.80  82.00 150.00   34
 65  \w     76.00 112.00   1.00    1.00    --   95.80  45.00  95.18   36
;
_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      -0.0655881000
_diffrn_orient_matrix_UB_12      0.0079234000
_diffrn_orient_matrix_UB_13      -0.1226116000
_diffrn_orient_matrix_UB_21      0.1781358000
_diffrn_orient_matrix_UB_22      -0.0682232000
_diffrn_orient_matrix_UB_23      -0.0046579000
_diffrn_orient_matrix_UB_31      -0.0615397000
_diffrn_orient_matrix_UB_32      -0.2064245000
_diffrn_orient_matrix_UB_33      -0.0031614000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15309
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.280
_diffrn_reflns_theta_min         5.733
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26323
_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    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_coef       0.0145(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0424P)^2^+0.1310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2824
_reflns_number_total             2836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00883h2.cif
_cod_data_source_block           exp_678
_cod_depositor_comments
'Adding full bibliography for 1562171--1562180.cif.'
_cod_database_code               1562176
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.93
_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:
 C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C14(H14A,H14B,
 H14C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              36569
_shelx_hkl_checksum              77995
_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 3.063
_oxdiff_exptl_absorpt_empirical_full_min 0.488