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_4034999
_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         'C9 H13 N O3 S2'
_chemical_formula_sum            'C9 H13 N O3 S2'
_chemical_formula_weight         247.32
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-31
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.477(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7654(4)
_cell_length_b                   9.6690(4)
_cell_length_c                   12.0922(9)
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    103.0
_cell_measurement_theta_max      29.4970
_cell_measurement_theta_min      2.9629
_cell_volume                     1138.28(11)
_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      103.0
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -45.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -13.5222  -84.0000  -66.0000 56

  2 omega   45.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.6785 -121.0000 -121.0000 25

  3 omega   -4.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.6785 -121.0000   38.0000 51

  4 omega  -43.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.6785  -37.0000   60.0000 81

  5 omega   -7.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.6785   77.0000   60.0000 93

  6 omega    0.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.6785   37.0000 -150.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0376751000
_diffrn_orient_matrix_UB_12      -0.0121154000
_diffrn_orient_matrix_UB_13      0.0516198000
_diffrn_orient_matrix_UB_21      -0.0130181000
_diffrn_orient_matrix_UB_22      -0.0719476000
_diffrn_orient_matrix_UB_23      -0.0056944000
_diffrn_orient_matrix_UB_31      0.0609508000
_diffrn_orient_matrix_UB_32      -0.0078220000
_diffrn_orient_matrix_UB_33      -0.0277006000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8602
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97154
_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            white
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+0.7281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                2016
_reflns_number_total             2221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03061_si_003.cif
_cod_data_source_block           exp_3940
_cod_database_code               4034999
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32