Organocatalytic cascade reactions for multi-functionalized chiral cyclic ethers through vinylidene <i>ortho</i>-quinone methides.
Jia, Shiqi; Chang, Yu; Tian, Yuhong; Mao, Hui; Qin, Wenling; Wang, Pengfei; Yan, Hailong; Chemical communications (Cambridge, England) 57 (2021) 11334–11337; doi:10.1039/d1cc05340j

data_7129059
_publ_section_title
;
 Organocatalytic cascade reactions for multi-functionalized chiral cyclic
 ethers through vinylidene <i>ortho</i>-quinone methides.
;
_journal_issue                   86
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11334
_journal_page_last               11337
_journal_paper_doi               10.1039/d1cc05340j
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H22 Br2 O3'
_chemical_formula_sum            'C32 H22 Br2 O3'
_chemical_formula_weight         614.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8735(3)
_cell_length_b                   13.6168(5)
_cell_length_c                   24.1689(10)
_cell_measurement_reflns_used    2481
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7970
_cell_measurement_theta_min      3.9080
_cell_volume                     2591.19(17)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_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     62.00  90.00   1.00   11.47    --   18.58 178.00  90.00   28
  2  \w    -44.00  53.00   1.00   11.47    --  -18.81  38.00 120.00   97
  3  \w    -75.00  -2.00   1.00   11.47    --  -18.81   0.00 120.00   73
;
_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      0.0788812000
_diffrn_orient_matrix_UB_12      0.0006520000
_diffrn_orient_matrix_UB_13      -0.0141675000
_diffrn_orient_matrix_UB_21      -0.0120995000
_diffrn_orient_matrix_UB_22      -0.0496808000
_diffrn_orient_matrix_UB_23      -0.0079050000
_diffrn_orient_matrix_UB_31      -0.0417518000
_diffrn_orient_matrix_UB_32      0.0156667000
_diffrn_orient_matrix_UB_33      -0.0244597000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10534
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.042
_diffrn_reflns_theta_min         3.372
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71683
_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            brown
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0230P)^2^+0.0878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.817
_reflns_number_gt                4360
_reflns_number_total             5957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05340j2.cif
_cod_data_source_block           20210412-yanhl-jsq-2899
_cod_depositor_comments          'Adding full bibliography for 7129059.cif.'
_cod_original_cell_volume        2591.18(19)
_cod_database_code               7129059
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H22 Br2 O3'
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C31(H31), C16(H16), C18(H18), C25(H25), C19(H19), C13(H13),
 C26(H26), C17(H17), C8(H8), C6(H6), C7(H7), C12(H12), C30(H30), C11(H11),
 C28(H28), C10(H10), C29(H29)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              43465
_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.763