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_1562175
_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         'C18 H24 O4'
_chemical_formula_sum            'C18 H24 O4'
_chemical_formula_weight         304.37
_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             2018-12-19
_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                 116.508(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8205(2)
_cell_length_b                   17.9401(3)
_cell_length_c                   6.9699(2)
_cell_measurement_reflns_used    10362
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1780
_cell_measurement_theta_min      4.9240
_cell_volume                     763.18(4)
_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 0.990
_diffrn_measured_fraction_theta_max 0.983
_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    -19.00  51.00   1.00    1.00    --    0.00  38.00   0.00   70
  2  \w    -23.00  68.00   1.00    1.00    --    0.00  57.00  90.00   91
  3  \w     58.00  89.00   1.00    1.00    --    0.00  82.00  30.00   31
  4  \w    -69.00   4.00   1.00    1.00    --    0.00 -38.00  60.00   73
  5  \w    -32.00   5.00   1.00    1.00    --    0.00  82.00  30.00   37
  6  \w     -5.00  88.00   1.00    1.00    --    0.00  57.00-150.00   93
  7  \w    -28.00  56.00   1.00    1.00    --    0.00  77.00 150.00   84
  8  \w     11.00  47.00   1.00    1.00    --    0.00  82.00  30.00   36
  9  \w     65.00  96.00   1.00    1.00    --   95.80  77.00  90.00   31
 10  \w     85.00 123.00   1.00    1.00    --   95.80 -77.00  60.00   38
 11  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 12  \w     98.00 124.00   1.00    1.00    --   95.80  77.00-180.00   26
 13  \w     72.00 180.00   1.00    1.00    --   95.80  61.00 -90.00  108
 14  \w    124.00 164.00   1.00    1.00    --   95.80  61.00-180.00   40
 15  \w     95.00 185.00   1.00    1.00    --   95.80  77.00 150.00   90
 16  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  30.00   26
 17  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 18  \w    111.00 180.00   1.00    1.00    --   95.80  77.00  60.00   69
 19  \w    143.00 172.00   1.00    1.00    --   95.80  77.00-150.00   29
 20  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 21  \w    121.00 147.00   1.00    1.00    --   95.80  77.00 -60.00   26
 22  \w      8.00  77.00   1.00    1.00    --   95.80 -77.00  60.00   69
 23  \w     75.00 111.00   1.00    1.00    --   95.80  45.00  60.00   36
 24  \w     76.00 154.00   1.00    1.00    --   95.80  45.00 150.00   78
 25  \w     65.00  93.00   1.00    1.00    --   95.80  77.00 -90.00   28
 26  \w    160.00 185.00   1.00    1.00    --   95.80  77.00 -90.00   25
 27  \w     51.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   77
 28  \w     74.00 101.00   1.00    1.00    --   95.80  61.00-180.00   27
 29  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 30  \w     72.00 148.00   1.00    1.00    --   95.80  61.00  90.00   76
 31  \w    111.00 184.00   1.00    1.00    --   95.80  82.00   0.00   73
 32  \w     65.00 125.00   1.00    1.00    --   95.80 -82.00   0.00   60
 33  \w     65.00  93.00   1.00    1.00    --   95.80  77.00  30.00   28
 34  \w     52.00 115.00   1.00    1.00    --   95.80 -82.00 -90.00   63
 35  \w     98.00 123.00   1.00    1.00    --   95.80  45.00  30.00   25
 36  \w    140.00 176.00   1.00    1.00    --   95.80  45.00  30.00   36
 37  \w     71.00 181.00   1.00    1.00    --   95.80  61.00 -30.00  110
 38  \w     63.00  99.00   1.00    1.00    --   95.80  82.00   0.00   36
 39  \w     63.00  95.00   1.00    1.00    --   95.80  82.00-180.00   32
 40  \w    148.00 174.00   1.00    1.00    --   95.80  82.00-120.00   26
 41  \w     67.00  93.00   1.00    1.00    --   95.80  82.00  90.00   26
 42  \w    131.00 185.00   1.00    1.00    --   95.80  82.00  90.00   54
 43  \w     92.00 127.00   1.00    1.00    --   95.80 -82.00  90.00   35
 44  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   26
 45  \w     75.00 100.00   1.00    1.00    --   95.80  45.00 -30.00   25
 46  \w     75.00 118.00   1.00    1.00    --   95.80  45.00-120.00   43
 47  \w     63.00  96.00   1.00    1.00    --   95.80  82.00 120.00   33
 48  \w     76.00 101.00   1.00    1.00    --   95.80  45.00  90.00   25
 49  \w     71.00 157.00   1.00    1.00    --   95.80  61.00   0.00   86
 50  \w    148.00 173.00   1.00    1.00    --   95.80  77.00  90.00   25
 51  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-150.00   26
 52  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 150.00   26
 53  \w     69.00 176.00   1.00    1.00    --   95.80  65.00-111.91  107
;
_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      -0.2149803000
_diffrn_orient_matrix_UB_12      0.0448363000
_diffrn_orient_matrix_UB_13      -0.0857698000
_diffrn_orient_matrix_UB_21      -0.1319331000
_diffrn_orient_matrix_UB_22      -0.0732196000
_diffrn_orient_matrix_UB_23      -0.0537567000
_diffrn_orient_matrix_UB_31      0.0101766000
_diffrn_orient_matrix_UB_32      -0.0004038000
_diffrn_orient_matrix_UB_33      0.2253021000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14686
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.290
_diffrn_reflns_theta_min         4.930
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55059
_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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0721P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2920
_reflns_number_total             3037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00883h2.cif
_cod_data_source_block           exp_594
_cod_depositor_comments
'Adding full bibliography for 1562171--1562180.cif.'
_cod_database_code               1562175
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.775
_reflns_odcompleteness_completeness 99.22
_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:
 C13(H13)
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), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              43304
_shelx_hkl_checksum              1009
_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 3.267
_oxdiff_exptl_absorpt_empirical_full_min 0.206