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_1562172
_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      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-04
_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                101.004(2)
_cell_angle_beta                 106.600(2)
_cell_angle_gamma                96.185(2)
_cell_formula_units_Z            4
_cell_length_a                   10.0882(2)
_cell_length_b                   11.6472(2)
_cell_length_c                   14.4851(3)
_cell_measurement_reflns_used    25453
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2670
_cell_measurement_theta_min      4.4930
_cell_volume                     1577.07(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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_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     40.00  66.00   1.00    1.00    --    0.00  57.00-120.00   26
  2  \w     59.00  86.00   1.00    1.00    --    0.00  38.00 150.00   27
  3  \w    -31.00  25.00   1.00    1.00    --    0.00  82.00-180.00   56
  4  \w    -62.00  23.00   1.00    1.00    --    0.00 -57.00-180.00   85
  5  \w     24.00  50.00   1.00    1.00    --    0.00  82.00 -90.00   26
  6  \w    -30.00   1.00   1.00    1.00    --    0.00  82.00 -90.00   31
  7  \w     51.00  88.00   1.00    1.00    --    0.00  82.00 -90.00   37
  8  \w     44.00  87.00   1.00    1.00    --    0.00  82.00-180.00   43
  9  \w    -16.00  18.00   1.00    1.00    --    0.00 -38.00 120.00   34
 10  \w     42.00  67.00   1.00    1.00    --    0.00  57.00-180.00   25
 11  \w    -23.00  42.00   1.00    1.00    --    0.00  19.00   0.00   65
 12  \w    -54.00 -28.00   1.00    1.00    --    0.00 -38.00 120.00   26
 13  \w    -17.00  34.00   1.00    1.00    --    0.00  38.00 150.00   51
 14  \w    -19.00  81.00   1.00    1.00    --    0.00  38.00  30.00  100
 15  \w    -23.00  22.00   1.00    1.00    --    0.00  57.00-120.00   45
 16  \w    -21.00  11.00   1.00    1.00    --    0.00  57.00-180.00   32
 17  \w     65.00 183.00   1.00    1.00    --   95.80  77.00  71.57  118
 18  \w    128.00 185.00   1.00    1.00    --   95.80  64.00-103.40   57
 19  \w    115.00 185.00   1.00    1.00    --   95.80  79.00   8.78   70
 20  \w     71.00  97.00   1.00    1.00    --   95.80  64.00-103.40   26
 21  \w     66.00 127.00   1.00    1.00    --   95.80 -82.00  60.00   61
 22  \w    159.00 185.00   1.00    1.00    --   95.80  76.00 -13.91   26
 23  \w     64.00  90.00   1.00    1.00    --   95.80  79.00   8.78   26
 24  \w     63.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   27
 25  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 26  \w     77.00 103.00   1.00    1.00    --   95.80  45.00 -60.00   26
 27  \w     78.00 105.00   1.00    1.00    --   95.80  45.00  60.00   27
 28  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 29  \w     65.00 148.00   1.00    1.00    --   95.80  77.00 150.00   83
 30  \w    150.00 176.00   1.00    1.00    --   95.80  77.00 150.00   26
 31  \w     76.00 141.00   1.00    1.00    --   95.80  42.00 -35.13   65
 32  \w     63.00 184.00   1.00    1.00    --   95.80  82.00-150.00  121
 33  \w    140.00 166.00   1.00    1.00    --   95.80  61.00  60.00   26
 34  \w     66.00  92.00   1.00    1.00    --   95.80  76.00 -13.91   26
 35  \w     71.00 122.00   1.00    1.00    --   95.80  61.00  60.00   51
 36  \w     33.00  74.00   1.00    1.00    --   95.80 -82.00 -30.00   41
 37  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00 -90.00  121
 38  \w     70.00 181.00   1.00    1.00    --   95.80  63.00  98.56  111
 39  \w     63.00 182.00   1.00    1.00    --   95.80  81.00-168.23  119
 40  \w     83.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   44
 41  \w     75.00 158.00   1.00    1.00    --   95.80  45.00   0.00   83
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 43  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 44  \w      9.00 114.00   1.00    1.00    --   95.80 -77.00 150.00  105
 45  \w     66.00  97.00   1.00    1.00    --   95.80  77.00 120.00   31
 46  \w     75.00 100.00   1.00    1.00    --   95.80  45.00 -90.00   25
 47  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 49  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 50  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 51  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-180.00   26
 52  \w     64.00  89.00   1.00    1.00    --   95.80  80.00 108.00   25
 53  \w     65.00 185.00   1.00    1.00    --   95.80  77.00   0.00  120
 54  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 55  \w     88.00 113.00   1.00    1.00    --   95.80 -82.00 120.00   25
 56  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 57  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 58  \w     47.00  84.00   1.00    1.00    --   95.80 -82.00 120.00   37
 59  \w     66.00 185.00   1.00    1.00    --   95.80  75.00 136.86  119
 60  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 150.00   26
 61  \w     58.00  83.00   1.00    1.00    --   95.80 -82.00-180.00   25
 62  \w     97.00 125.00   1.00    1.00    --   95.80 -82.00-180.00   28
 63  \w     70.00  96.00   1.00    1.00    --   95.80  63.00-171.65   26
 64  \w    145.00 185.00   1.00    1.00    --   95.80  42.00 -35.13   40
 65  \w     70.00 103.00   1.00    1.00    --   95.80  63.00 -12.59   33
 66  \w     76.00 134.00   1.00    1.00    --   95.80  36.00 -59.88   58
;
_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      0.0656955000
_diffrn_orient_matrix_UB_12      -0.0150937000
_diffrn_orient_matrix_UB_13      0.1059733000
_diffrn_orient_matrix_UB_21      -0.0177254000
_diffrn_orient_matrix_UB_22      -0.1349610000
_diffrn_orient_matrix_UB_23      -0.0403258000
_diffrn_orient_matrix_UB_31      0.1467693000
_diffrn_orient_matrix_UB_32      0.0164657000
_diffrn_orient_matrix_UB_33      -0.0128351000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36802
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.520
_diffrn_reflns_theta_min         3.925
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36233
_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    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 4906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_coef       0.0022(3)
_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   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         11615
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0528P)^2^+0.1658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                11303
_reflns_number_total             11615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00883h2.cif
_cod_data_source_block           exp_937
_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        1577.06(6)
_cod_original_formula_moiety     '4(C18 H24 O4)'
_cod_original_formula_sum        'C72 H96 O16'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1217.48
_cod_database_code               1562172
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.881
_shelx_estimated_absorpt_t_min   0.802
_reflns_odcompleteness_completeness 99.70
_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:
 C46(H46), C68(H68), C10(H10), C60(H60), C44(H44), C19(H19), C25(H25), C8(H8A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C48(H48A,H48B), C47(H47A,H47B), C23(H23A,H23B),
 C49(H49A,H49B), C43(H43A,H43B), C61(H61A,H61B), C32(H32A,H32B), C57(H57A,H57B),
  C50(H50A,H50B), C20(H20A,H20B), C21(H21A,H21B), C58(H58A,H58B), C59(H59A,
 H59B), C13(H13A,H13B), C11(H11A,H11B), C69(H69A,H69B), C22(H22A,H22B),
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C28(H28), C64(H64), C40(H40), C65(H65), C3(H3A), C39(H39), C29(H29)
2.d Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C72(H72A,H72B,H72C), C53(H53A,H53B,H53C), C36(H36A,H36B,
 H36C), C34(H34A,H34B,H34C), C52(H52A,H52B,H52C), C16(H16A,H16B,H16C), C15(H15A,
 H15B,H15C), C71(H71A,H71B,H71C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C),
 C02G(H02A,H02B,H02C)
2.e Idealised tetrahedral OH refined as rotating group:
 O15(H15), O3(H3), O8(H8)
;
_shelx_res_checksum              75902
_shelx_hkl_checksum              67246
_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 2.452
_oxdiff_exptl_absorpt_empirical_full_min 0.522