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_7133412
_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_formula_moiety         '2(C22 H17 Br O2)'
_chemical_formula_sum            'C44 H34 Br2 O4'
_chemical_formula_weight         786.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-15
_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                 92.223(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.1188(8)
_cell_length_b                   7.6926(2)
_cell_length_c                   15.6637(5)
_cell_measurement_reflns_used    8621
_cell_measurement_temperature    200.01(10)
_cell_measurement_theta_max      28.5290
_cell_measurement_theta_min      3.5940
_cell_volume                     3385.61(17)
_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_environment      N~2~
_diffrn_ambient_temperature      200.01(10)
_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 0.893
_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    -36.00  48.00   1.00   27.50    --   18.58 -19.00 120.00   84
  2  \w    -50.00  27.00   1.00   27.50    --   18.58 -38.00  60.00   77
  3  \w    -44.00  34.00   1.00   27.50    --   18.58 -57.00-120.00   78
  4  \w    -42.00  11.00   1.00   27.50    --  -18.78 -77.00 -60.00   53
  5  \w    -39.00  11.00   1.00   27.50    --  -18.78 -77.00-150.00   50
  6  \w    -80.00  -4.00   1.00   27.50    --  -18.78 -57.00  30.00   76
;
_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      0.0113368000
_diffrn_orient_matrix_UB_12      -0.0228455000
_diffrn_orient_matrix_UB_13      0.0396827000
_diffrn_orient_matrix_UB_21      0.0063130000
_diffrn_orient_matrix_UB_22      0.0882340000
_diffrn_orient_matrix_UB_23      0.0070328000
_diffrn_orient_matrix_UB_31      -0.0216608000
_diffrn_orient_matrix_UB_32      0.0137852000
_diffrn_orient_matrix_UB_33      0.0207320000
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27434
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.036
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75813
_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    1.543
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.652
_refine_diff_density_min         -1.488
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0781
_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^)+38.4785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6205
_reflns_number_total             8072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           20220114-lk-zzx-1474-up
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133412
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N Br'
_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
2.a Ternary CH refined with riding coordinates:
 C00R(H00R), C00T(H00T), C012(H012), C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C010(H01F,H01G)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00F(H00F), C00G(H00G), C00M(H00M), C00N(H00N),
 C00O(H00O), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C013(H013), C015(H015), C018(H018), C019(H019), C01A(H01D), C01C(H01K),
 C01D(H01L), C01E(H01E)
2.d Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C016(H01H,H01I,H01J)
;
_shelx_res_checksum              19336
_shelx_hkl_checksum              37011
_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.807