Catalytic asymmetric construction of bridged bicyclo[<i>m</i>.3.1] rings using an intramolecular Diels-Alder reaction.
Li, Kai; Zhao, Zhengxing; Qin, Wenling; Liu, Yidong; Yan, Hailong; Chemical communications (Cambridge, England) 60 (2024) 9570–9573; doi:10.1039/d4cc02850c

data_7133411
_publ_section_title
;
 Catalytic asymmetric construction of bridged bicyclo[<i>m</i>.3.1] rings
 using an intramolecular Diels-Alder reaction.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9570
_journal_page_last               9573
_journal_paper_doi               10.1039/d4cc02850c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.34
_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             2022-02-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.0554(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.48375(11)
_cell_length_b                   23.7768(5)
_cell_length_c                   8.95801(13)
_cell_measurement_reflns_used    10596
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      71.6240
_cell_measurement_theta_min      4.9430
_cell_volume                     1589.99(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00 -60.00   88
  2  \w    -90.00  -3.00   1.00    1.00    --  -35.97 126.00 -90.00   87
  3  \w    -33.00  55.00   1.00    1.00    --   35.97 -38.00-150.00   88
  4  \w      1.00  75.00   1.00    1.00    --   35.97 -99.00-180.00   74
  5  \w     19.00 103.00   1.00    1.00    --   35.97  57.00  30.00   84
  6  \w     87.00 178.00   1.00    1.00    --  107.97  30.00 -60.00   91
  7  \w     38.00 129.00   1.00    1.00    --  107.97 -30.00 -60.00   91
  8  \w     91.00 176.00   1.00    1.00    --  107.97  45.00  30.00   85
  9  \w     39.00 110.00   1.00    1.00    --  107.97 -95.00 -90.00   71
 10  \w     41.00 126.00   1.00    1.00    --  107.97 -61.00 120.00   85
 11  \w     39.00 110.00   1.00    1.00    --  107.97 -95.00  90.00   71
 12  \w     40.00 125.00   1.00    1.00    --  107.97 -45.00-150.00   85
 13  \w     39.00 110.00   1.00    1.00    --  107.97 -95.00  30.00   71
 14  \w   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00-150.00   95
 15  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
 16  \w   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00 -60.00   95
 17  \w    -31.00  53.00   1.00    1.00    --   35.97 -57.00  60.00   84
 18  \w     87.00 178.00   1.00    1.00    --  107.97  30.00-120.00   91
 19  \w     81.00 176.00   1.00    1.00    --  107.97  77.00 -30.00   95
 20  \w     70.00 178.00   1.00    1.00    --  107.97  15.00 150.00  108
 21  \w     91.00 176.00   1.00    1.00    --  107.97  45.00  60.00   85
 22  \w     91.00 176.00   1.00    1.00    --  107.97  45.00-180.00   85
 23  \w     81.00 141.00   1.00    1.00    --  107.97  77.00 -60.00   60
 24  \w     81.00 176.00   1.00    1.00    --  107.97  77.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0093427000
_diffrn_orient_matrix_UB_12      0.0054691000
_diffrn_orient_matrix_UB_13      0.1717989000
_diffrn_orient_matrix_UB_21      -0.2050703000
_diffrn_orient_matrix_UB_22      -0.0062043000
_diffrn_orient_matrix_UB_23      -0.0029191000
_diffrn_orient_matrix_UB_31      0.0205045000
_diffrn_orient_matrix_UB_32      -0.0642601000
_diffrn_orient_matrix_UB_33      0.0148865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15193
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.700
_diffrn_reflns_theta_min         4.949
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.3349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.668
_reflns_Friedel_fraction_max     0.651
_reflns_number_gt                5051
_reflns_number_total             5126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           2bg-c_zzx-913-new
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133411
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'C1 H1 O1'
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.751
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C33(H33A,H33B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
  C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
 C37(H37), C38(H38), C39(H39), C40(H40)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              71368
_shelx_hkl_checksum              26417
_shelx_fab_checksum              98866
_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 1.969
_oxdiff_exptl_absorpt_empirical_full_min 0.590