Selective Addition of Secondary Amines to C60: Formation of Penta- and Hexaamino[60]fullerenes.
Li, Yanbang; Gan, Liangbing; The Journal of organic chemistry 79 (2014) 8912–8916; doi:10.1021/jo5015867

data_4029908
_publ_section_title
;
 Selective Addition of Secondary Amines to C60: Formation of Penta- and
 Hexaamino[60]fullerenes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8912
_journal_page_last               8916
_journal_paper_doi               10.1021/jo5015867
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C80 H40 N5 O1, 2(C S2)'
_chemical_formula_sum            'C82 H41 N5 O S4'
_chemical_formula_weight         1240.44
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                67.063(6)
_cell_angle_beta                 88.451(5)
_cell_angle_gamma                61.280(6)
_cell_formula_units_Z            2
_cell_length_a                   14.0793(8)
_cell_length_b                   14.2340(9)
_cell_length_c                   16.9088(10)
_cell_measurement_reflns_used    4777
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      27.6770
_cell_measurement_theta_min      3.3530
_cell_volume                     2682.4(4)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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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      179.99(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.8161
_diffrn_measurement_details
;
  1 omega   -9.00   77.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   57.0000 -180.0000 86

  2 omega  -63.00   36.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -57.0000   30.0000 99

  3 omega  -75.00   13.00   1.0000    1.7000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -57.0000 -120.0000 88
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0411559000
_diffrn_orient_matrix_UB_12      0.0576342000
_diffrn_orient_matrix_UB_13      -0.0303357000
_diffrn_orient_matrix_UB_21      -0.0191847000
_diffrn_orient_matrix_UB_22      -0.0252635000
_diffrn_orient_matrix_UB_23      -0.0195953000
_diffrn_orient_matrix_UB_31      -0.0370598000
_diffrn_orient_matrix_UB_32      -0.0001166000
_diffrn_orient_matrix_UB_33      0.0292505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17683
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.859
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64945
_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    1.536
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     860
_refine_ls_number_reflns         10504
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0712
_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^)+(0.0683P)^2^+3.4678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6444
_reflns_number_total             10504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5015867_si_003.cif
_cod_data_source_block           exp_3660
_cod_depositor_comments
'Adding full bibliography for 4029907--4029908.cif.'
_cod_original_cell_volume        2682.4(3)
_cod_database_code               4029908
_chemical_oxdiff_formula         C23H18Cl1O4
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Rigid bond restraints
 N3, C69
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C69) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 1*[Sof(O1)]+1*[Sof(O1A)]+1*[Sof(O1B)]+1*[Sof(O1C)]=1 with esd of 0.0001
5.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,
 H65B), C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B),
 C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B),
  C75(H75A,H75B), C76(H76A,H76B), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,
 H79B), C80(H80A,H80B)
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.988
_shelxl_version_number           2013-3