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_7134667
_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         '2(C31 H29 N O8)'
_chemical_formula_sum            'C62 H58 N2 O16'
_chemical_formula_weight         1087.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 110.983(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0372(3)
_cell_length_b                   9.66930(10)
_cell_length_c                   26.7286(4)
_cell_measurement_reflns_used    14980
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6540
_cell_measurement_theta_min      3.5230
_cell_volume                     5317.76(14)
_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                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.968
_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    -44.00  12.00   0.50    1.00    --    0.00 -77.00 120.00  112
  2  \w    -21.00  29.00   0.50    1.00    --    0.00 -82.00   0.00  100
  3  \w     21.00  85.00   0.50    1.00    --    0.00  38.00 150.00  128
  4  \w    -14.00  29.00   0.50    1.00    --    0.00 -82.00 -90.00   86
  5  \w    146.00 174.00   0.50    3.00    --   95.80  82.00  30.00   56
  6  \w     76.00 185.00   0.50    3.00    --   95.80  45.00 -30.00  218
  7  \w     85.00 115.00   0.50    3.00    --   95.80 -45.00 150.00   60
  8  \w     94.00 119.00   0.50    3.00    --   95.80 -61.00-150.00   50
  9  \w     88.00 129.00   0.50    3.00    --   95.80  82.00  30.00   82
 10  \w    109.00 160.00   0.50    3.00    --   95.80  82.00-180.00  102
 11  \w      6.00  54.00   0.50    3.00    --   95.80 -61.00-150.00   96
 12  \w     34.00 119.00   0.50    3.00    --   95.80 -61.00-180.00  170
 13  \w    147.00 176.00   0.50    3.00    --   95.80  82.00-150.00   58
 14  \w     79.00 184.00   0.50    3.00    --   95.80  45.00 -60.00  210
 15  \w     94.00 169.00   0.50    3.00    --   95.80  30.00 -90.00  150
;
_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      0.0149491000
_diffrn_orient_matrix_UB_12      -0.0414939000
_diffrn_orient_matrix_UB_13      0.0588790000
_diffrn_orient_matrix_UB_21      -0.0404125000
_diffrn_orient_matrix_UB_22      -0.1327825000
_diffrn_orient_matrix_UB_23      -0.0186286000
_diffrn_orient_matrix_UB_31      0.0612044000
_diffrn_orient_matrix_UB_32      -0.0776334000
_diffrn_orient_matrix_UB_33      0.0003707000
_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  0.0591
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            30744
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_min         3.236
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82374
_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    1.358
_exptl_crystal_description       plate
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         10519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0955P)^2^+1.4269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8938
_reflns_number_total             10519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02347e2.cif
_cod_data_source_block           tr9-rac_collect
_cod_depositor_comments
'Adding full bibliography for 7134660--7134669.cif.'
_cod_database_code               7134667
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C248 H232 N8 O64 '
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 99.79
_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:
 C4(H4), C5(H5), C3(H3), C6(H6), C42(H42), C8(H8), C46(H46), C47(H47),
 C44(H44), C45(H45)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C31(H31), C30(H30), C22(H22), C21(H21), C66(H66), C20(H20),
 C12(H12), C28(H28), C19(H19), C62(H62), C61(H61), C67(H67), C16(H16), C58(H58),
  C69(H69), C68(H68), C59(H59), C14(H14), C15(H15), C13(H13), C56(H56),
 C52(H52), C54(H54), C55(H55), C53(H53)
2.c Idealised Me refined as rotating group:
 C80(H80A,H80B,H80C), C36(H36A,H36B,H36C), C76(H76A,H76B,H76C), C40(H40A,H40B,
 H40C), C33(H33A,H33B,H33C), C64(H64A,H64B,H64C)
2.d Idealised tetrahedral OH refined as rotating group:
 O39(H39), O38(H38), O77(H77), O79(H79)
;
_shelx_res_checksum              43524
_shelx_hkl_checksum              71197
_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 2.847
_oxdiff_exptl_absorpt_empirical_full_min 0.444