Copper-Catalyzed Aerobic Oxidative Reaction of C<sub>60</sub> with Aliphatic Primary Amines and CS<sub>2</sub>.
Wu, Sheng-Li; Gao, Xiang; The Journal of organic chemistry 83 (2018) 2125–2130; doi:10.1021/acs.joc.7b03061

data_4034998
_publ_section_title
;
 Copper-Catalyzed Aerobic Oxidative Reaction of C<sub>60</sub> with
 Aliphatic Primary Amines and CS<sub>2</sub>.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2125
_journal_page_last               2130
_journal_paper_doi               10.1021/acs.joc.7b03061
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         '2(C32.5 H4.5 N0.5 S), 2(C0.25 S0.5)'
_chemical_formula_sum            'C65.5 H9 N S3'
_chemical_formula_weight         905.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-29
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.462(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0873(8)
_cell_length_b                   13.9444(13)
_cell_length_c                   12.7124(19)
_cell_measurement_reflns_used    1867
_cell_measurement_temperature    103.3
_cell_measurement_theta_max      29.6403
_cell_measurement_theta_min      3.0314
_cell_volume                     1714.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      103.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -14.00   17.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772 -111.0000  163.0000 31

  2 omega   -8.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000  -60.0000 94

  3 omega   -6.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000   60.0000 91

  4 omega   27.00   61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000 -120.0000 34

  5 omega  -34.00   -5.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000  150.0000 29

  6 omega  -49.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -77.0000  -90.0000 51

  7 omega  -49.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000   30.0000 85
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0244360000
_diffrn_orient_matrix_UB_12      0.0426046000
_diffrn_orient_matrix_UB_13      0.0297089000
_diffrn_orient_matrix_UB_21      -0.0565728000
_diffrn_orient_matrix_UB_22      0.0257567000
_diffrn_orient_matrix_UB_23      -0.0342407000
_diffrn_orient_matrix_UB_31      -0.0396944000
_diffrn_orient_matrix_UB_32      -0.0104860000
_diffrn_orient_matrix_UB_33      0.0366159000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14234
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             914
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.8890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                2478
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03061_si_002.cif
_cod_data_source_block           exp_3270
_cod_original_formula_sum        'C65.50 H9 N S3'
_cod_database_code               4034998
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32