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_7134663
_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 N O7'
_chemical_formula_sum            'C32 H29 N O7'
_chemical_formula_weight         539.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                102.425(3)
_cell_angle_beta                 99.324(3)
_cell_angle_gamma                101.043(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3074(3)
_cell_length_b                   10.5620(4)
_cell_length_c                   12.7619(4)
_cell_measurement_reflns_used    5577
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8340
_cell_measurement_theta_min      3.6460
_cell_volume                     1301.40(8)
_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      149.99(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.960
_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  19.00   0.50    1.00    --    0.00 -82.00-150.00   98
  2  \w    -44.00  28.00   0.50    1.00    --    0.00 -77.00 -90.00  144
  3  \w    -33.00  26.00   0.50    1.00    --    0.00 -82.00  30.00  118
  4  \w    -21.00  28.00   0.50    1.00    --    0.00 -82.00 -30.00   98
  5  \w     -4.00  21.00   0.50    1.00    --    0.00 -82.00 120.00   50
  6  \w     52.00 110.00   0.50    1.80    --   95.80 -30.00 150.00  116
  7  \w     29.00 123.00   0.50    1.80    --   95.80 -82.00 -60.00  188
  8  \w     27.00 119.00   0.50    1.80    --   95.80 -82.00  30.00  184
  9  \w     11.00  86.00   0.50    1.80    --   95.80 -61.00 -60.00  150
 10  \w     70.00 126.00   0.50    1.80    --   95.80 -82.00 120.00  112
 11  \w      9.00  86.00   0.50    1.80    --   95.80 -30.00  60.00  154
 12  \w    102.00 127.00   0.50    1.80    --   95.80 -82.00  60.00   50
 13  \w      8.00  52.00   0.50    1.80    --   95.80 -82.00 150.00   88
 14  \w     94.00 126.00   0.50    1.80    --   95.80 -82.00 150.00   64
 15  \w     63.00 105.00   0.50    1.80    --   95.80 -82.00-120.00   84
 16  \w      6.00 119.00   0.50    1.80    --   95.80 -15.00 120.00  226
 17  \w     53.00  78.00   0.50    1.80    --   95.80 -77.00-150.00   50
 18  \w    114.00 184.00   0.50    1.80    --   95.80   0.00-180.00  140
 19  \w     10.00  91.00   0.50    1.80    --   95.80 -61.00  30.00  162
 20  \w     60.00 118.00   0.50    1.80    --   95.80 -61.00  90.00  116
 21  \w     40.00 101.00   0.50    1.80    --   95.80   0.00-180.00  122
;
_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      0.1479273000
_diffrn_orient_matrix_UB_12      -0.0105919000
_diffrn_orient_matrix_UB_13      0.0062963000
_diffrn_orient_matrix_UB_21      -0.0400407000
_diffrn_orient_matrix_UB_22      -0.1453855000
_diffrn_orient_matrix_UB_23      0.0077080000
_diffrn_orient_matrix_UB_31      -0.0282026000
_diffrn_orient_matrix_UB_32      -0.0485962000
_diffrn_orient_matrix_UB_33      -0.1260947000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12729
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.539
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86418
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0481P)^2^+0.5315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4312
_reflns_number_total             5112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02347e2.cif
_cod_data_source_block           fck8-rac_collect
_cod_depositor_comments
'Adding full bibliography for 7134660--7134669.cif.'
_cod_database_code               7134663
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C64 H58 N2 O14 '
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.61
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C3(H3), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C27(H27), C6(H6), C25(H25), C28(H28), C21(H21), C31(H31),
 C12(H12), C13(H13), C30(H30), C24(H24), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C33(H33A,H33B,H33C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              84315
_shelx_hkl_checksum              1727
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.740