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_1562178
_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         'C19 H26 O4'
_chemical_formula_sum            'C19 H26 O4'
_chemical_formula_weight         318.39
_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             2019-06-20
_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                 115.900(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2554(2)
_cell_length_b                   19.3711(3)
_cell_length_c                   10.2742(2)
_cell_measurement_reflns_used    22645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.3030
_cell_measurement_theta_min      4.5260
_cell_volume                     1657.02(6)
_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    -48.00  10.00   1.00    1.00    --    0.00 -19.00-128.00   58
  2  \w     24.00  50.00   1.00    1.00    --    0.00  19.00  38.00   26
  3  \w     71.00 176.00   1.00    1.00    --   95.80  19.00  38.00  105
  4  \w     61.00  87.00   1.00    1.00    --   95.80 -19.00-128.00   26
  5  \w    -16.00  22.00   1.00    1.00    --    0.00  57.00   0.00   38
  6  \w     37.00  88.00   1.00    1.00    --    0.00  38.00-180.00   51
  7  \w     33.00  89.00   1.00    1.00    --    0.00  57.00 120.00   56
  8  \w    -23.00   9.00   1.00    1.00    --    0.00  57.00  60.00   32
  9  \w    -19.00  68.00   1.00    1.00    --    0.00  38.00   0.00   87
 10  \w     53.00  79.00   1.00    1.00    --    0.00  57.00   0.00   26
 11  \w    -19.00  33.00   1.00    1.00    --    0.00  38.00-180.00   52
 12  \w    -23.00  29.00   1.00    1.00    --    0.00  57.00 120.00   52
 13  \w    -21.00  53.00   1.00    1.00    --    0.00  57.00-120.00   74
 14  \w     13.00  69.00   1.00    1.00    --    0.00  57.00  60.00   56
 15  \w    -87.00  19.00   1.00    1.00    --    0.00 -38.00  60.00  106
 16  \w     50.00  77.00   1.00    1.00    --    0.00  82.00 -90.00   27
 17  \w    -27.00   5.00   1.00    1.00    --    0.00  82.00 -90.00   32
 18  \w    153.00 184.00   1.00    1.00    --   95.80  77.00 -30.00   31
 19  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 20  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 21  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 22  \w    149.00 175.00   1.00    1.00    --   95.80  82.00  60.00   26
 23  \w      6.00 126.00   1.00    1.00    --   95.80 -77.00   0.00  120
 24  \w     79.00 128.00   1.00    1.00    --   95.80 -82.00-180.00   49
 25  \w    141.00 167.00   1.00    1.00    --   95.80  45.00-180.00   26
 26  \w     75.00 118.00   1.00    1.00    --   95.80  45.00-180.00   43
 27  \w     63.00 100.00   1.00    1.00    --   95.80  82.00 -90.00   37
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  12.94   26
 29  \w    131.00 157.00   1.00    1.00    --   95.80  82.00  12.94   26
 30  \w     68.00  98.00   1.00    1.00    --   95.80  71.00-131.57   30
 31  \w    140.00 170.00   1.00    1.00    --   95.80  71.00-131.57   30
 32  \w     73.00 119.00   1.00    1.00    --   95.80  54.00  17.07   46
 33  \w     67.00  92.00   1.00    1.00    --   95.80  72.00  88.37   25
 34  \w     40.00  67.00   1.00    1.00    --   95.80 -82.00  60.00   27
 35  \w     64.00  89.00   1.00    1.00    --   95.80  82.00  60.00   25
 36  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 37  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 38  \w    140.00 166.00   1.00    1.00    --   95.80  82.00 120.00   26
 39  \w    116.00 144.00   1.00    1.00    --   95.80  77.00-180.00   28
 40  \w     65.00  92.00   1.00    1.00    --   95.80  77.00  60.00   27
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 42  \w     78.00 127.00   1.00    1.00    --   95.80 -82.00-120.00   49
 43  \w     94.00 183.00   1.00    1.00    --   95.80  77.00-100.11   89
 44  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-100.11   26
 45  \w     14.00  67.00   1.00    1.00    --   95.80 -82.00-120.00   53
 46  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 47  \w     39.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   88
 48  \w     75.00 110.00   1.00    1.00    --   95.80  45.00 -30.00   35
 49  \w     71.00 184.00   1.00    1.00    --   95.80  61.00-180.00  113
 50  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 51  \w     38.00 127.00   1.00    1.00    --   95.80 -82.00 150.00   89
 52  \w     71.00  97.00   1.00    1.00    --   95.80  61.00   0.00   26
 53  \w     64.00  93.00   1.00    1.00    --   95.80  82.00 120.00   29
 54  \w     71.00 178.00   1.00    1.00    --   95.80  61.00-150.00  107
 55  \w     75.00 180.00   1.00    1.00    --   95.80  50.00  84.10  105
 56  \w     75.00 101.00   1.00    1.00    --   95.80  47.00 -43.72   26
 57  \w    120.00 185.00   1.00    1.00    --   95.80  47.00 -43.72   65
 58  \w     74.00 102.00   1.00    1.00    --   95.80  56.00 115.04   28
 59  \w     72.00 173.00   1.00    1.00    --   95.80  55.00  58.71  101
 60  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 61  \w     74.00 120.00   1.00    1.00    --   95.80  54.00  43.48   46
 62  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  60.00   26
 63  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 64  \w     75.00 140.00   1.00    1.00    --   95.80  45.00 150.00   65
 65  \w     75.00 101.00   1.00    1.00    --   95.80  45.00   0.00   26
 66  \w     86.00 126.00   1.00    1.00    --   95.80 -82.00  60.00   40
 67  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  30.00   26
 68  \w     92.00 117.00   1.00    1.00    --   95.80  77.00-150.00   25
 69  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 70  \w     22.00  75.00   1.00    1.00    --   95.80 -82.00-180.00   53
 71  \w     65.00 178.00   1.00    1.00    --   95.80  77.00-120.00  113
;
_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      0.1707455000
_diffrn_orient_matrix_UB_12      0.0143598000
_diffrn_orient_matrix_UB_13      0.1182020000
_diffrn_orient_matrix_UB_21      -0.0571833000
_diffrn_orient_matrix_UB_22      -0.0142287000
_diffrn_orient_matrix_UB_23      0.1175232000
_diffrn_orient_matrix_UB_31      0.0425860000
_diffrn_orient_matrix_UB_32      -0.0769192000
_diffrn_orient_matrix_UB_33      0.0002380000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            37450
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.565
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51615
_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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0652P)^2^+0.2424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                5499
_reflns_number_total             5673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00883h2.cif
_cod_data_source_block           exp_907
_cod_depositor_comments
;
Adding full bibliography for 1562171--1562180.cif.

2022-05-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1657.01(6)
_cod_original_formula_moiety     '2(C19 H26 O4)'
_cod_original_formula_sum        'C38 H52 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     636.79
_cod_database_code               1562178
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.97
_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:
 C7(H7), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C15(H15a,H15b), C10(H10a,H10b), C29(H29a,H29b), C14(H14a,
 H14b), C12(H12a,H12b), C30(H30a,H30b), C13(H13a,H13b), C32(H32a,H32b),
 C33(H33a,H33b), C34(H34a,H34b), C31(H31a,H31b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C4(H4), C3(H3a), C35(H35), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C36(H36a,H36b,H36c), C37(H37a,H37b,
 H37c), C19(H19a,H19b,H19c), C38(H38a,H38b,H38c)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O3(H3)
;
_shelx_res_checksum              71504
_shelx_hkl_checksum              6866
_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 2.073
_oxdiff_exptl_absorpt_empirical_full_min 0.465