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_1562171
_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         'C17 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.34
_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             2018-12-04
_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                 99.6040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6905(2)
_cell_length_b                   12.90170(10)
_cell_length_c                   11.27500(10)
_cell_measurement_reflns_used    19351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0690
_cell_measurement_theta_min      5.2400
_cell_volume                     1533.32(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.990
_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    -87.00  19.00   1.00    1.00    --    0.00 -38.00  30.00  106
  2  \w    -16.00  44.00   1.00    1.00    --    0.00  19.00-180.00   60
  3  \w    -19.00  10.00   1.00    1.00    --    0.00  38.00 -60.00   29
  4  \w     21.00  54.00   1.00    1.00    --    0.00  82.00  90.00   33
  5  \w     40.00  71.00   1.00    1.00    --    0.00  77.00-150.00   31
  6  \w     24.00  85.00   1.00    1.00    --    0.00  38.00 -60.00   61
  7  \w    -30.00  32.00   1.00    1.00    --    0.00  77.00-150.00   62
  8  \w    -15.00  63.00   1.00    1.00    --    0.00  82.00-120.00   78
  9  \w    -31.00  19.00   1.00    1.00    --    0.00  82.00  90.00   50
 10  \w    -15.00  84.00   1.00    1.00    --    0.00  38.00   0.00   99
 11  \w     52.00  82.00   1.00    1.00    --    0.00  19.00-180.00   30
 12  \w      6.00 116.00   1.00    1.00    --   95.80 -82.00 120.00  110
 13  \w     73.00 183.00   1.00    1.00    --   95.80  53.00 113.45  110
 14  \w     59.00 107.00   1.00    1.00    --   95.80 -82.00  60.00   48
 15  \w      6.00 120.00   1.00    1.00    --   95.80 -61.00-120.00  114
 16  \w    160.00 185.00   1.00    1.00    --   95.80  82.00-175.04   25
 17  \w    155.00 185.00   1.00    1.00    --   95.80  64.00 149.50   30
 18  \w     74.00 149.00   1.00    1.00    --   95.80  50.00  20.94   75
 19  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 20  \w     63.00  97.00   1.00    1.00    --   95.80  82.00-175.04   34
 21  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 22  \w      6.00 116.00   1.00    1.00    --   95.80 -82.00-120.00  110
 23  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 24  \w    103.00 185.00   1.00    1.00    --   95.80  77.00-150.00   82
 25  \w     64.00  91.00   1.00    1.00    --   95.80  82.00  30.00   27
 26  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 27  \w    112.00 138.00   1.00    1.00    --   95.80  82.00 -60.00   26
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 29  \w     93.00 185.00   1.00    1.00    --   95.80  82.00 167.16   92
 30  \w     65.00  97.00   1.00    1.00    --   95.80  77.00-120.00   32
 31  \w     70.00 101.00   1.00    1.00    --   95.80  64.00 149.50   31
 32  \w     65.00  92.00   1.00    1.00    --   95.80  77.00  60.00   27
 33  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 34  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 35  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   27
 36  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 167.16   26
 37  \w     75.00 166.00   1.00    1.00    --   95.80  45.00   0.00   91
 38  \w     72.00  97.00   1.00    1.00    --   95.80  61.00  90.00   25
 39  \w     74.00 100.00   1.00    1.00    --   95.80  61.00 -60.00   26
 40  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 41  \w     71.00 158.00   1.00    1.00    --   95.80  61.00-120.00   87
 42  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 43  \w     76.00 152.00   1.00    1.00    --   95.80  45.00  90.00   76
 44  \w    123.00 178.00   1.00    1.00    --   95.80  82.00  60.00   55
 45  \w     41.00 106.00   1.00    1.00    --   95.80 -82.00   0.00   65
 46  \w     72.00  97.00   1.00    1.00    --   95.80  61.00 120.00   25
 47  \w      6.00 104.00   1.00    1.00    --   95.80 -61.00 120.00   98
 48  \w     76.00 102.00   1.00    1.00    --   95.80  30.00-120.00   26
 49  \w     75.00 115.00   1.00    1.00    --   95.80  61.00-180.00   40
 50  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 51  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  90.00   26
 52  \w     77.00 103.00   1.00    1.00    --   95.80  30.00 -60.00   26
 53  \w     76.00 123.00   1.00    1.00    --   95.80  45.00 -60.00   47
 54  \w     73.00 110.00   1.00    1.00    --   95.80  61.00  30.00   37
 55  \w     65.00  91.00   1.00    1.00    --   95.80  82.00-120.00   26
 56  \w     63.00  89.00   1.00    1.00    --   95.80  81.00 138.77   26
 57  \w     69.00 179.00   1.00    1.00    --   95.80  65.00 126.11  110
 58  \w    123.00 173.00   1.00    1.00    --   95.80  51.00 -31.85   50
 59  \w     74.00 107.00   1.00    1.00    --   95.80  51.00 -31.85   33
;
_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      -0.0595064000
_diffrn_orient_matrix_UB_12      0.1081548000
_diffrn_orient_matrix_UB_13      0.0060218000
_diffrn_orient_matrix_UB_21      -0.0096261000
_diffrn_orient_matrix_UB_22      0.0112716000
_diffrn_orient_matrix_UB_23      -0.1372317000
_diffrn_orient_matrix_UB_31      -0.1332073000
_diffrn_orient_matrix_UB_32      -0.0492638000
_diffrn_orient_matrix_UB_33      -0.0182130000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33570
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.410
_diffrn_reflns_theta_min         3.976
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21024
_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    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6136
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0626P)^2^+0.0552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                5734
_reflns_number_total             6136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00883h2.cif
_cod_data_source_block           exp_576
_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_formula_moiety     '2(C17 H22 O4)'
_cod_original_formula_sum        'C34 H44 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     580.69
_cod_database_code               1562171
_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), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C27(H27A,H27B), C28(H28A,
 H28B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7A)
;
_shelx_res_checksum              69032
_shelx_hkl_checksum              87452
_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 4.323
_oxdiff_exptl_absorpt_empirical_full_min 0.533