Synthesis and chemical reactivity of tetrahydro[60]fullerene epoxides with both amino and aryl addends.
Liang, Sisi; Xu, Liang; Gan, Liangbing; The Journal of organic chemistry 80 (2015) 3957–3964; doi:10.1021/acs.joc.5b00287

data_4036159
_publ_section_title
;
 Synthesis and chemical reactivity of tetrahydro[60]fullerene epoxides
 with both amino and aryl addends.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3957
_journal_page_last               3964
_journal_paper_doi               10.1021/acs.joc.5b00287
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C84 H41 N3 O'
_chemical_formula_sum            'C84 H41 N3 O'
_chemical_formula_weight         1108.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-07-27
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.204(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.1629(8)
_cell_length_b                   20.3663(4)
_cell_length_c                   19.4299(3)
_cell_measurement_reflns_used    29154
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.8950
_cell_measurement_theta_min      3.2770
_cell_volume                     13105.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9131
_diffrn_measurement_details
;
  1 omega   -7.00   60.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579 -111.0000  -33.0643 67

  2 omega  -45.00   40.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -57.0000 -180.0000 85

  3 omega  -14.00   67.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   77.0000   30.0000 81

  4 omega   -5.00   87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   38.0000  150.0000 92

  5 omega  -59.00   37.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -38.0000   90.0000 96

  6 omega  -20.00   92.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   19.0000  -90.0000 112

  7 omega  -20.00   30.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -99.0000 -120.0000 50

  8 omega  -70.00  -24.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  126.0000  -20.1878 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0047861000
_diffrn_orient_matrix_UB_12      -0.0322739000
_diffrn_orient_matrix_UB_13      0.0089794000
_diffrn_orient_matrix_UB_21      -0.0207029000
_diffrn_orient_matrix_UB_22      0.0059260000
_diffrn_orient_matrix_UB_23      -0.0159516000
_diffrn_orient_matrix_UB_31      0.0027159000
_diffrn_orient_matrix_UB_32      -0.0116771000
_diffrn_orient_matrix_UB_33      -0.0328947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            96995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.063
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description
;
;
_exptl_crystal_F_000             4592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     796
_refine_ls_number_reflns         12844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0817
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1490P)^2^+12.5457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2338
_refine_ls_wR_factor_ref         0.2481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9286
_reflns_number_total             12844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00287_si_002.cif
_cod_data_source_block           exp_3894-sr
_cod_database_code               4036159
_chemical_oxdiff_formula         C77H22N3O1
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 Riding coordinates:
 C3(H3), C9(H9), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B),
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B),
  C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C)
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.993
_shelxl_version_number           2013-3