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_7133415
_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 H15 Br O2'
_chemical_formula_sum            'C21 H15 Br O2'
_chemical_formula_weight         379.24
_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             2021-11-17
_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                 114.336(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8697(4)
_cell_length_b                   22.6968(7)
_cell_length_c                   8.9630(5)
_cell_measurement_reflns_used    4427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8520
_cell_measurement_theta_min      4.2130
_cell_volume                     1644.05(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.895
_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     38.00  95.00   1.00    4.00    --   18.74-178.00 -90.00   57
  2  \w    -12.00  91.00   1.00    4.00    --   18.74  19.00-120.00  103
  3  \w     48.00  83.00   1.00    4.00    --   18.74  57.00-120.00   35
  4  \w     46.00  72.00   1.00    4.00    --   18.74 178.00 -30.00   26
  5  \w    -64.00  25.00   1.00    4.00    --  -18.85 -19.00 -30.00   89
  6  \w    -41.00  36.00   1.00    4.00    --  -18.85  38.00 120.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0574829000
_diffrn_orient_matrix_UB_12      0.0048946000
_diffrn_orient_matrix_UB_13      -0.0819763000
_diffrn_orient_matrix_UB_21      0.0469931000
_diffrn_orient_matrix_UB_22      0.0245828000
_diffrn_orient_matrix_UB_23      -0.0051090000
_diffrn_orient_matrix_UB_31      0.0468252000
_diffrn_orient_matrix_UB_32      -0.0186635000
_diffrn_orient_matrix_UB_33      -0.0282931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13047
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.012
_diffrn_reflns_theta_min         3.591
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0257P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                5045
_reflns_number_total             7480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           20211117-zzx-968
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133415
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H15 Br O2'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C14(H14A,H14B), C35(H35A,H35B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C2(H2), C23(H23), C24(H24), C28(H28), C19(H19), C37(H37), C7(H7),
 C40(H40), C25(H25), C8(H8), C38(H38), C26(H26), C5(H5), C39(H39), C16(H16),
 C3(H3), C18(H18), C17(H17), C4(H4)
;
_shelx_res_checksum              729
_shelx_hkl_checksum              68090
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.799