Synthesis of Fullerotetrahydroquinolines via [4 + 2] Cycloaddition Reaction of [60]Fullerene with in Situ Generated Aza-o-quinone Methides.
Jiang, Sheng-Peng; Lu, Wen-Qiang; Liu, Zhan; Wang, Guan-Wu; The Journal of organic chemistry 83 (2018) 1959–1968; doi:10.1021/acs.joc.7b02897

data_4034985
_publ_section_title
;
 Synthesis of Fullerotetrahydroquinolines via [4 + 2] Cycloaddition
 Reaction of [60]Fullerene with in Situ Generated Aza-o-quinone Methides.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1959
_journal_page_last               1968
_journal_paper_doi               10.1021/acs.joc.7b02897
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C14 H14 Cl2 Cu N2 O S'
_chemical_formula_weight         392.77
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                94.801(3)
_cell_angle_beta                 95.419(3)
_cell_angle_gamma                108.835(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4487(2)
_cell_length_b                   9.8574(3)
_cell_length_c                   11.7142(4)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      70.9800
_cell_measurement_theta_min      4.7600
_cell_volume                     804.44(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4878
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.096
_diffrn_reflns_theta_min         3.819
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0220(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0821P)^2^+0.1839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2888
_reflns_number_total             3003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02897_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4034985
_shelx_estimated_absorpt_t_min   0.307
_shelx_estimated_absorpt_t_max   0.344
_shelxl_version_number           2013-4
_shelx_res_checksum              69347
_shelx_hkl_checksum              34779