Preparation of Azafullerene C59NR5 and Fullerene Derivative C60NAr5 with a Pyridine Moiety on the Cage Skeleton.
Lou, Ning; Li, Yanbang; Cui, Chengxing; Liu, Yajun; Gan, Liangbing; Organic letters 18 (2016) 2236–2239; doi:10.1021/acs.orglett.6b00872

data_1543142
_publ_section_title
;
 Preparation of Azafullerene C59NR5 and Fullerene Derivative C60NAr5 with
 a Pyridine Moiety on the Cage Skeleton.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2236
_journal_page_last               2239
_journal_paper_doi               10.1021/acs.orglett.6b00872
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C90 H21 Cl F5 N'
_chemical_formula_sum            'C90 H21 Cl F5 N'
_chemical_formula_weight         1246.53
_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             2015-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                91.044(6)
_cell_angle_beta                 108.456(6)
_cell_angle_gamma                109.296(6)
_cell_formula_units_Z            2
_cell_length_a                   13.9563(9)
_cell_length_b                   14.4188(10)
_cell_length_c                   15.4405(11)
_cell_measurement_reflns_used    4691
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.1260
_cell_measurement_theta_min      3.2900
_cell_volume                     2755.5(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
;
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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.866
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega   13.00   39.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -57.0000   60.0000 26

  2 omega  -62.00   39.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -57.0000 -150.0000 101

  3 omega  -55.00   26.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -38.0000  -90.0000 81

  4 omega   67.00  101.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  178.0000  -60.0000 34

  5 omega   47.00   92.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454 -178.0000 -120.0000 45

  6 omega    4.00   44.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   38.0000   60.0000 40

  7 omega  -19.00   30.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -99.0000  -60.0000 49

  8 omega  -86.00  -59.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -38.0000 -150.0000 27

  9 omega  -93.00  -56.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  178.0000  -60.0000 37
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0563794000
_diffrn_orient_matrix_UB_12      0.0245352000
_diffrn_orient_matrix_UB_13      0.0223757000
_diffrn_orient_matrix_UB_21      -0.0102005000
_diffrn_orient_matrix_UB_22      0.0280576000
_diffrn_orient_matrix_UB_23      0.0319835000
_diffrn_orient_matrix_UB_31      0.0007602000
_diffrn_orient_matrix_UB_32      -0.0371413000
_diffrn_orient_matrix_UB_33      0.0294394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_Laue_measured_fraction_full 0.866
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24752
_diffrn_reflns_point_group_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.106
_diffrn_reflns_theta_min         2.884
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96908
_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    1.502
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     893
_refine_ls_number_reflns         8642
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0976
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1536P)^2^+1.4069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2564
_refine_ls_wR_factor_ref         0.2894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5062
_reflns_number_total             8642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00872_si_002.cif
_cod_data_source_block           exp_5451-sr
_cod_depositor_comments          'Adding full bibliography for 1543142.cif.'
_cod_database_code               1543142
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C90 H1 Cl1 N1 F5'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.81
_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 N(H) groups
2. Restrained distances
 C33-N1B
 1.5 with sigma of 0.01
 C32-N1B
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq, Uanis(Cl1B) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.005
Uanis(C30) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.2
Uanis(N1B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
4. Others
 Sof(Cl1B)=Sof(N1B)=Sof(H1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(N1A)=Sof(H1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
  C27(H27), C29(H29), C30(H30), N1A(H1A), N1B(H1B)
;
_olex2_submission_special_instructions 'No special instructions were received'