Carbene-organocatalyzed enantioselective [5+5] annulation of dienols and dienals towards tetrahydroisochromen-1-ones.
Xu, Ke; Zhao, Jiayi; Lin, Kejun; Zhu, Tingshun; Chemical communications (Cambridge, England) 61 (2025) 10602–10605; doi:10.1039/d5cc02347e

data_7134669
_publ_section_title
;
 Carbene-organocatalyzed enantioselective [5+5] annulation of dienols and
 dienals towards tetrahydroisochromen-1-ones.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10602
_journal_page_last               10605
_journal_paper_doi               10.1039/d5cc02347e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C31 H28 Br2 O5'
_chemical_formula_sum            'C31 H28 Br2 O5'
_chemical_formula_weight         640.35
_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             2023-02-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2025-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.45320(10)
_cell_length_b                   14.99130(10)
_cell_length_c                   12.68540(10)
_cell_measurement_reflns_used    12134
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      74.0960
_cell_measurement_theta_min      3.5450
_cell_volume                     2696.37(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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    -27.00  17.00   0.50    0.50    --    0.00 -38.00 -30.00   88
  2  \w    -31.00  -2.00   0.50    0.50    --    0.00 -82.00-120.00   58
  3  \w    -33.00  -2.00   0.50    0.50    --    0.00 -82.00 150.00   62
  4  \w    -28.00  29.00   0.50    0.50    --    0.00 -82.00 -90.00  114
  5  \w     71.00 102.00   0.50    0.50    --   95.80 -82.00 -30.00   62
  6  \w     56.00  87.00   0.50    0.50    --   95.80 -61.00 120.00   62
  7  \w     15.00  57.00   0.50    0.50    --   95.80 -30.00  60.00   84
  8  \w    136.00 185.00   0.50    0.50    --   95.80  30.00-120.00   98
  9  \w     89.00 167.00   0.50    0.50    --   95.80  45.00-150.00  156
 10  \w     79.00 117.00   0.50    0.50    --   95.80  30.00-120.00   76
 11  \w     73.00 161.00   0.50    0.50    --   95.80  15.00   0.00  176
 12  \w     34.00 127.00   0.50    0.50    --   95.80 -82.00  30.00  186
 13  \w     66.00 108.00   0.50    0.50    --   95.80 -30.00  60.00   84
 14  \w      8.00 116.00   0.50    0.50    --   95.80 -61.00  30.00  216
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0326126000
_diffrn_orient_matrix_UB_12      -0.0041642000
_diffrn_orient_matrix_UB_13      -0.1229703000
_diffrn_orient_matrix_UB_21      0.1032432000
_diffrn_orient_matrix_UB_22      -0.0100016000
_diffrn_orient_matrix_UB_23      -0.0130636000
_diffrn_orient_matrix_UB_31      -0.0086366000
_diffrn_orient_matrix_UB_32      -0.1022029000
_diffrn_orient_matrix_UB_33      0.0062857000
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15346
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.502
_diffrn_reflns_theta_min         4.292
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (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    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+2.2895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5130
_reflns_number_total             5330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02347e2.cif
_cod_data_source_block           tr16-fck39_collect
_cod_depositor_comments
'Adding full bibliography for 7134660--7134669.cif.'
_cod_database_code               7134669
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C124 H116 Br8 N4 O16 '
_shelx_estimated_absorpt_t_max   0.615
_shelx_estimated_absorpt_t_min   0.523
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C15(H15), C17(H17), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C26(H26), C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C31(H31A,H31B,H31C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.599