Synthesis of homoazafullerene [C59N(CH2)]R and azahomoazafullerene [C59N(NH)]R
Xu, Dan; Li, Yanbang; Lou, Ning; Gan, Liangbing; Organic Chemistry Frontiers 4 (2017) 750–; doi:10.1039/C7QO00098G

data_1553736
_publ_section_title
;
 Synthesis of homoazafullerene [C59N(CH2)]R and azahomoazafullerene
 [C59N(NH)]R
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              750
_journal_paper_doi               10.1039/C7QO00098G
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C76 H38 Br N O8'
_chemical_formula_sum            'C76 H38 Br N O8'
_chemical_formula_weight         1172.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-12-14 deposited with the CCDC.
2017-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.444(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8397(9)
_cell_length_b                   24.2642(13)
_cell_length_c                   16.7166(13)
_cell_measurement_reflns_used    2689
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      24.1730
_cell_measurement_theta_min      3.3940
_cell_volume                     5293.4(7)
_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, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -20.00   52.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -99.0000   90.0000 72

  2 omega  -12.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   57.0000  -90.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0127320000
_diffrn_orient_matrix_UB_12      -0.0271233000
_diffrn_orient_matrix_UB_13      -0.0158553000
_diffrn_orient_matrix_UB_21      0.0376119000
_diffrn_orient_matrix_UB_22      -0.0107809000
_diffrn_orient_matrix_UB_23      0.0366887000
_diffrn_orient_matrix_UB_31      -0.0370718000
_diffrn_orient_matrix_UB_32      -0.0016185000
_diffrn_orient_matrix_UB_33      0.0207163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1648
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.072
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61067
_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_density_diffrn    1.472
_exptl_crystal_F_000             2400
_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         0.735
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     787
_refine_ls_number_reflns         10314
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0705P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5220
_reflns_number_total             10314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00098g2.cif
_cod_data_source_block           exp_6568-sr
_cod_database_code               1553736
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C76 N1 O8 Br1'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.920
_reflns_odcompleteness_completeness 99.02
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.01
Uanis(C49) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.002
Uanis(C57) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C63) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,
 H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,
 H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'