Synthesis of [60]fullerene-fused dihydroindolizines via copper-catalyzed dearomative N-heteroannulation
Zhang, Qian-Wen; Liu, Yuanyuan; Yin, Zheng-Chun; Qiu, Wen-Jie; Huang, Xinmin; Li, Jian-Feng; Wang, Guan-Wu; Chemical Communications 61 (2025) 5653–5656; doi:10.1039/D5CC00820D

data_7134335
_publ_section_title
;
 Synthesis of [60]fullerene-fused dihydroindolizines via copper-catalyzed
 dearomative N-heteroannulation
;
_journal_issue                   30
_journal_name_full               'Chemical Communications'
_journal_page_first              5653
_journal_page_last               5656
_journal_paper_doi               10.1039/D5CC00820D
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C S2, C69 H9 N O2'
_chemical_formula_sum            'C70 H9 N O2 S2'
_chemical_formula_weight         959.90
_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             2023-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-18 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.966(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8911(2)
_cell_length_b                   14.7000(2)
_cell_length_c                   20.0129(4)
_cell_measurement_reflns_used    4803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7760
_cell_measurement_theta_min      4.6530
_cell_volume                     3646.14(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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     -1.00  33.00   1.00    4.00    --  -41.76  38.00  30.00   34
  2  \w    -66.00 -31.00   1.00    4.00    --  -41.76  38.00  30.00   35
  3  \w    -83.00  -6.00   1.00    4.00    --  -41.76 125.00 150.00   77
  4  \w   -114.00 -20.00   1.00    4.00    --  -41.76 -38.00  60.00   94
  5  \w    113.00 153.00   1.00    8.00    --  106.05  77.00  90.00   40
  6  \w     55.00 134.00   1.00    8.00    --  106.05 -77.00 150.00   79
  7  \w     34.00 127.00   1.00    8.00    --  106.05 -45.00   0.00   93
  8  \w     39.00 134.00   1.00    8.00    --  106.05 -61.00 -90.00   95
  9  \w     71.00 111.00   1.00    8.00    --  106.05-125.00  90.00   40
 10  \w     56.00 102.00   1.00    8.00    --  106.05-125.00-180.00   46
 11  \w    127.00 175.00   1.00    8.00    --  106.05  30.00-120.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0370747000
_diffrn_orient_matrix_UB_12      -0.0881682000
_diffrn_orient_matrix_UB_13      0.0412499000
_diffrn_orient_matrix_UB_21      -0.0996064000
_diffrn_orient_matrix_UB_22      -0.0500746000
_diffrn_orient_matrix_UB_23      -0.0454100000
_diffrn_orient_matrix_UB_31      0.0644500000
_diffrn_orient_matrix_UB_32      -0.0265526000
_diffrn_orient_matrix_UB_33      -0.0514365000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14855
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.078
_diffrn_reflns_theta_min         3.566
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         7077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0739P)^2^+0.8520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5317
_reflns_number_total             7077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00820d2.cif
_cod_data_source_block           zqw20230821-1_auto
_cod_depositor_comments          'Adding full bibliography for 7134335.cif.'
_cod_database_code               7134335
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C70H6O2N1
_reflns_odcompleteness_completeness 99.91
_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 Secondary CH2 refined with riding coordinates:
 C020(H02A,H02B)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C01B(H01B), C01S(H01S), C01Y(H01Y)
2.c Idealised Me refined as rotating group:
 C023(H02C,H02D,H02E)
;
_shelx_res_checksum              45366
_shelx_hkl_checksum              83260
_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 3.220
_oxdiff_exptl_absorpt_empirical_full_min 0.458