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_7134666
_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         'C32 H29 F O5'
_chemical_formula_sum            'C32 H29 F O5'
_chemical_formula_weight         512.55
_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             2023-02-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-02-25 deposited with the CCDC.	2025-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.427(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7735(2)
_cell_length_b                   28.0445(5)
_cell_length_c                   8.8667(2)
_cell_measurement_reflns_used    6368
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8340
_cell_measurement_theta_min      4.2320
_cell_volume                     2594.48(9)
_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 1.5 (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_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    -30.00   4.00   0.50    1.00    --    0.00 -82.00-180.00   68
  2  \w     41.00  68.00   0.50    1.00    --    0.00  38.00 -90.00   54
  3  \w    -16.00  31.00   0.50    1.00    --    0.00  38.00 -90.00   94
  4  \w    -33.00  30.00   0.50    1.00    --    0.00 -82.00-120.00  126
  5  \w     13.00 113.00   0.50    7.00    --   95.80 -45.00  60.00  200
  6  \w     12.00  45.00   0.50    7.00    --   95.80 -30.00 150.00   66
  7  \w    134.00 184.00   0.50    7.00    --   95.80   0.00 -30.00  100
  8  \w     52.00 104.00   0.50    7.00    --   95.80 -45.00 -90.00  104
  9  \w     83.00 112.00   0.50    7.00    --   95.80 -30.00 150.00   58
 10  \w      8.00  55.00   0.50    7.00    --   95.80 -15.00 -90.00   94
 11  \w     92.00 118.00   0.50    7.00    --   95.80 -15.00 -90.00   52
 12  \w     12.00 112.00   0.50    7.00    --   95.80 -30.00-120.00  200
 13  \w     95.00 122.00   0.50    7.00    --   95.80   0.00 -30.00   54
 14  \w      7.00  76.00   0.50    7.00    --   95.80   0.00 -30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1269869000
_diffrn_orient_matrix_UB_12      0.0253454000
_diffrn_orient_matrix_UB_13      -0.0768999000
_diffrn_orient_matrix_UB_21      -0.0663943000
_diffrn_orient_matrix_UB_22      -0.0261744000
_diffrn_orient_matrix_UB_23      0.1112998000
_diffrn_orient_matrix_UB_31      0.0358219000
_diffrn_orient_matrix_UB_32      0.0410887000
_diffrn_orient_matrix_UB_33      0.1177993000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13083
_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         74.186
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69690
_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    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1092P)^2^+0.2899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.1942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3815
_reflns_number_total             5108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02347e2.cif
_cod_data_source_block           23rac_collect
_cod_depositor_comments
'Adding full bibliography for 7134660--7134669.cif.'
_cod_database_code               7134666
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C132 H128 N4 O20 '
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained planarity
 C19, F1, C20', C21, C22, C23, C24
 with sigma of 0.1
 C19, F1', C20, C21', C22', C23', C24'
 with sigma of 0.1
3. Rigid body (RIGU) restrains
 F1, C20', C21, C22, C23, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1', C20, C21', C22', C23', C24'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(F1')=Sof(C20)=Sof(H20)=Sof(C21')=Sof(H21')=Sof(C22')=Sof(H22')=Sof(C23')=
 Sof(H23')=Sof(C24')=1-FVAR(1)
 Sof(F1)=Sof(C20')=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C20(H20),
 C21'(H21'), C22'(H22'), C23'(H23')
5.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C31(H31A,H31B,H31C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              31954
_shelx_hkl_checksum              24641
_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 1.633
_oxdiff_exptl_absorpt_empirical_full_min 0.709