#------------------------------------------------------------------------------
#$Date: 2021-12-16 13:43:25 +0200 (Thu, 16 Dec 2021) $
#$Revision: 271475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/65/4106572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4106572
loop_
_publ_author_name
'Huaping Li'
'Chad Risko'
'Jung Hwa Seo'
'Casey Campbell'
'Guang Wu'
'Jean-Luc Brédas'
'Guillermo C. Bazan'
_publ_section_title
;
 Fullerene-Carbene Lewis Acid-Base Adducts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12410
_journal_page_last               12413
_journal_paper_doi               10.1021/ja204974m
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C87 H36 N2'
_chemical_formula_weight         1109.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.382(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.215(6)
_cell_length_b                   18.138(9)
_cell_length_c                   17.386(8)
_cell_measurement_temperature    293(2)
_cell_volume                     3655(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_sigmaI/netI    0.1058
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19587
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.191
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1644
_refine_diff_density_max         8.174
_refine_diff_density_min         -1.415
_refine_diff_density_rms         0.572
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.469
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.469
_refine_ls_R_factor_all          0.4684
_refine_ls_R_factor_gt           0.4000
_refine_ls_shift/su_max          0.096
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.7571
_refine_ls_wR_factor_ref         0.7908
_reflns_number_gt                4114
_reflns_number_total             7426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja204974m_si_001.cif
_cod_data_source_block           plot
_cod_depositor_comments
;

2021-12-16
Formula fixed to be consistent with given Z
                 miguel
;
_cod_original_formula_sum            'C120 H30 Cl3 N3'
_cod_original_formula_weight         1619.82
_cod_original_cell_volume        3656(3)
_cod_database_code               4106572
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N N 0.4894(9) 0.3095(7) 0.2212(6) 0.020(3) Uani 1 1 d .
C3 C 0.4732(11) 0.3874(7) 0.1981(8) 0.021(3) Uani 1 1 d .
C4 C 0.5774(13) 0.2875(9) 0.2900(9) 0.029(4) Uani 1 1 d .
H4 H 0.6266 0.3182 0.3285 0.035 Uiso 1 1 calc R
C66 C 0.4360(15) 0.2500 0.1797(12) 0.018(4) Uani 1 2 d S
C8 C 0.4003(12) 0.4286(9) 0.2298(9) 0.029(4) Uani 1 1 d .
C9 C 0.3358(15) 0.2500 0.1014(12) 0.018(4) Uani 1 2 d S
C10 C 0.5369(11) 0.4160(8) 0.1520(9) 0.024(3) Uani 1 1 d .
C11 C 0.3605(13) 0.3115(11) -0.0252(10) 0.039(4) Uani 1 1 d .
C12 C 0.3746(16) 0.2500 0.0251(13) 0.032(6) Uani 1 2 d S
C13 C 0.3912(14) 0.5038(9) 0.2089(10) 0.034(4) Uani 1 1 d .
H13 H 0.3446 0.5341 0.2285 0.041 Uiso 1 1 calc R
C14 C 0.5227(13) 0.4891(9) 0.1329(10) 0.031(4) Uani 1 1 d .
H14 H 0.5628 0.5098 0.1007 0.038 Uiso 1 1 calc R
C15 C -0.2203(18) 0.2500 -0.2212(16) 0.042(6) Uani 1 2 d S
C16 C 0.2510(14) 0.3157(9) 0.0946(9) 0.032(4) Uani 1 1 d .
C17 C -0.1636(18) 0.2500 -0.2791(12) 0.028(5) Uani 1 2 d S
C18 C 0.3370(14) 0.3970(10) 0.2835(9) 0.030(4) Uani 1 1 d .
H18 H 0.328(14) 0.344(10) 0.273(10) 0.036 Uiso 1 1 calc .
C19 C 0.4494(13) 0.5337(9) 0.1604(10) 0.030(4) Uani 1 1 d .
H19 H 0.4401 0.5833 0.1459 0.037 Uiso 1 1 calc R
C20 C -0.0982(15) 0.3143(10) -0.2912(9) 0.038(4) Uani 1 1 d .
C21 C 0.3070(18) 0.3781(12) -0.0146(13) 0.059(6) Uani 1 1 d .
C22 C 0.6245(13) 0.3701(10) 0.1241(10) 0.033(4) Uani 1 1 d .
H22 H 0.602(14) 0.318(11) 0.123(10) 0.040 Uiso 1 1 calc .
C23 C 0.0042(14) 0.2866(11) -0.3082(9) 0.047(5) Uani 1 1 d .
C24 C 0.2446(16) 0.3760(9) 0.0430(12) 0.046(5) Uani 1 1 d .
C25 C 0.6283(15) 0.3897(10) 0.0414(11) 0.041(5) Uani 1 1 d .
H25A H 0.5512 0.3918 0.0043 0.061 Uiso 1 1 calc R
H25B H 0.6715 0.3530 0.0235 0.061 Uiso 1 1 calc R
H25C H 0.6648 0.4368 0.0433 0.061 Uiso 1 1 calc R
C26 C 0.3527(14) 0.2874(12) -0.1077(10) 0.056(6) Uani 1 1 d .
C27 C 0.2175(15) 0.4300(10) 0.2701(11) 0.044(5) Uani 1 1 d .
H27A H 0.2252 0.4805 0.2876 0.066 Uiso 1 1 calc R
H27B H 0.1782 0.4027 0.3007 0.066 Uiso 1 1 calc R
H27C H 0.1740 0.4278 0.2135 0.066 Uiso 1 1 calc R
C28 C 0.015(2) 0.4169(11) -0.2105(13) 0.069(7) Uani 1 1 d .
C29 C -0.0915(17) 0.3751(10) -0.2439(12) 0.053(5) Uani 1 1 d .
C30 C -0.2010(15) 0.2917(16) -0.0880(15) 0.081(9) Uani 1 1 d .
C31 C 0.0449(17) 0.3289(17) 0.0792(12) 0.066(7) Uani 1 1 d .
C32 C 0.1492(13) 0.2894(12) 0.1107(9) 0.049(6) Uani 1 1 d .
C33 C 0.2138(15) 0.2897(14) -0.2436(10) 0.071(8) Uani 1 1 d .
C34 C -0.078(2) 0.4172(11) -0.1141(14) 0.061(7) Uani 1 1 d .
C35 C 0.139(2) 0.4156(10) 0.0120(13) 0.059(6) Uani 1 1 d .
C36 C -0.0633(15) 0.2871(15) 0.0482(12) 0.081(11) Uani 1 1 d .
C37 C 0.2868(18) 0.3256(17) -0.1745(12) 0.070(8) Uani 1 1 d .
C38 C 0.024(2) 0.4406(10) -0.1310(16) 0.074(8) Uani 1 1 d .
C39 C -0.1501(17) 0.3752(10) -0.1826(13) 0.049(5) Uani 1 1 d .
C40 C 0.115(2) 0.3900(14) -0.2269(13) 0.064(7) Uani 1 1 d .
C41 C 0.1087(17) 0.3279(15) -0.2769(11) 0.062(7) Uani 1 1 d .
C42 C 0.4095(17) 0.4080(13) 0.3741(10) 0.053(5) Uani 1 1 d .
H42A H 0.4840 0.3856 0.3842 0.079 Uiso 1 1 calc R
H42B H 0.3705 0.3855 0.4081 0.079 Uiso 1 1 calc R
H42C H 0.4188 0.4598 0.3859 0.079 Uiso 1 1 calc R
C43 C 0.039(2) 0.3914(15) 0.0308(14) 0.074(8) Uani 1 1 d .
C44 C -0.2107(15) 0.3182(15) -0.1718(10) 0.055(6) Uani 1 1 d .
C46 C -0.1375(18) 0.326(2) -0.0239(12) 0.082(10) Uani 1 1 d .
C47 C 0.231(2) 0.4149(12) -0.0847(16) 0.072(8) Uani 1 1 d .
C48 C 0.7456(15) 0.3782(12) 0.1863(12) 0.050(5) Uani 1 1 d .
H48A H 0.8011 0.3543 0.1662 0.075 Uiso 1 1 calc R
H48B H 0.7466 0.3559 0.2366 0.075 Uiso 1 1 calc R
H48C H 0.7644 0.4296 0.1949 0.075 Uiso 1 1 calc R
C50 C 0.130(2) 0.4394(10) -0.0704(14) 0.075(8) Uani 1 1 d .
C53 C -0.070(2) 0.3967(16) -0.0380(16) 0.081(9) Uani 1 1 d .
C54 C 0.2249(19) 0.3915(15) -0.1629(15) 0.070(8) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C66 N C4 110.1(12) . .
C66 N C3 128.6(12) . .
C4 N C3 120.9(12) . .
C10 C3 C8 124.9(13) . .
C10 C3 N 117.9(12) . .
C8 C3 N 117.0(12) . .
C4 C4 N 106.6(8) 4_565 .
C4 C4 H4 126.7 4_565 .
N C4 H4 126.7 . .
N C66 N 106.4(16) . 4_565
N C66 C9 126.8(8) . .
N C66 C9 126.8(8) 4_565 .
C3 C8 C13 115.0(14) . .
C3 C8 C18 123.8(14) . .
C13 C8 C18 121.2(13) . .
C66 C9 C12 113.1(15) . .
C66 C9 C16 113.3(10) . 4_565
C12 C9 C16 108.2(11) . 4_565
C66 C9 C16 113.3(10) . .
C12 C9 C16 108.2(11) . .
C16 C9 C16 99.7(16) 4_565 .
C14 C10 C3 117.0(13) . .
C14 C10 C22 119.6(13) . .
C3 C10 C22 123.4(13) . .
C12 C11 C21 124.9(17) . .
C12 C11 C26 109.3(18) . .
C21 C11 C26 119.3(17) . .
C11 C12 C11 106(2) 4_565 .
C11 C12 C9 122.0(12) 4_565 .
C11 C12 C9 122.0(12) . .
C19 C13 C8 121.8(14) . .
C19 C13 H13 119.1 . .
C8 C13 H13 119.1 . .
C10 C14 C19 121.7(14) . .
C10 C14 H14 119.2 . .
C19 C14 H14 119.2 . .
C17 C15 C44 116.8(13) . .
C17 C15 C44 116.8(13) . 4_565
C44 C15 C44 112(2) . 4_565
C24 C16 C32 120.4(16) . .
C24 C16 C9 123.1(15) . .
C32 C16 C9 109.1(15) . .
C15 C17 C20 121.5(11) . .
C15 C17 C20 121.5(11) . 4_565
C20 C17 C20 105(2) . 4_565
C8 C18 C27 114.2(14) . .
C8 C18 C42 109.8(13) . .
C27 C18 C42 108.3(14) . .
C8 C18 H18 108(10) . .
C27 C18 H18 109(9) . .
C42 C18 H18 108(10) . .
C13 C19 C14 119.5(14) . .
C13 C19 H19 120.3 . .
C14 C19 H19 120.3 . .
C29 C20 C23 120.4(17) . .
C29 C20 C17 119.4(17) . .
C23 C20 C17 107.2(16) . .
C11 C21 C24 115.9(16) . .
C11 C21 C47 119(2) . .
C24 C21 C47 105(2) . .
C25 C22 C48 109.8(13) . .
C25 C22 C10 114.0(14) . .
C48 C22 C10 109.5(14) . .
C25 C22 H22 108(10) . .
C48 C22 H22 108(10) . .
C10 C22 H22 107(10) . .
C23 C23 C41 121.6(13) 4_565 .
C23 C23 C20 110.0(10) 4_565 .
C41 C23 C20 117.4(19) . .
C16 C24 C35 120(2) . .
C16 C24 C21 122.2(16) . .
C35 C24 C21 109.7(19) . .
C22 C25 H25A 109.5 . .
C22 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C22 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C26 C26 C37 120.3(15) 4_565 .
C26 C26 C11 107.2(11) 4_565 .
C37 C26 C11 121(2) . .
C18 C27 H27A 109.5 . .
C18 C27 H27B 109.4 . .
H27A C27 H27B 109.5 . .
C18 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C38 C28 C40 119(2) . .
C38 C28 C29 110(2) . .
C40 C28 C29 117(2) . .
C20 C29 C39 119.3(18) . .
C20 C29 C28 123(2) . .
C39 C29 C28 106.8(19) . .
C46 C30 C44 121(3) . .
C46 C30 C30 118.6(19) . 4_565
C44 C30 C30 108.6(14) . 4_565
C43 C31 C32 121(2) . .
C43 C31 C36 109.2(19) . .
C32 C31 C36 118(2) . .
C31 C32 C32 120.5(14) . 4_565
C31 C32 C16 119(2) . .
C32 C32 C16 109.3(10) 4_565 .
C37 C33 C41 112(2) . .
C37 C33 C33 117.5(15) . 4_565
C41 C33 C33 119.4(14) . 4_565
C53 C34 C38 119(2) . .
C53 C34 C39 120(3) . .
C38 C34 C39 109(2) . .
C24 C35 C43 120(2) . .
C24 C35 C50 108(2) . .
C43 C35 C50 120(2) . .
C36 C36 C46 118.6(16) 4_565 .
C36 C36 C31 121.0(14) 4_565 .
C46 C36 C31 108(2) . .
C26 C37 C33 122(3) . .
C26 C37 C54 119(2) . .
C33 C37 C54 106(2) . .
C50 C38 C28 120(3) . .
C50 C38 C34 120(3) . .
C28 C38 C34 107(2) . .
C44 C39 C34 121(2) . .
C44 C39 C29 122.0(18) . .
C34 C39 C29 107(2) . .
C41 C40 C28 120.9(18) . .
C41 C40 C54 110(2) . .
C28 C40 C54 119(2) . .
C33 C41 C40 105.9(18) . .
C33 C41 C23 119(2) . .
C40 C41 C23 121(2) . .
C18 C42 H42A 109.5 . .
C18 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C18 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
C31 C43 C35 120.0(18) . .
C31 C43 C53 113(3) . .
C35 C43 C53 114(3) . .
C39 C44 C15 121.0(18) . .
C39 C44 C30 121(2) . .
C15 C44 C30 105(2) . .
C30 C46 C36 123(3) . .
C30 C46 C53 117(2) . .
C36 C46 C53 108(2) . .
C54 C47 C50 119(2) . .
C54 C47 C21 120(3) . .
C50 C47 C21 111(2) . .
C22 C48 H48A 109.5 . .
C22 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C22 C48 H48C 109.4 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C38 C50 C47 122(3) . .
C38 C50 C35 121(3) . .
C47 C50 C35 106.1(19) . .
C34 C53 C43 125(3) . .
C34 C53 C46 120(2) . .
C43 C53 C46 102(2) . .
C47 C54 C40 120(3) . .
C47 C54 C37 120(2) . .
C40 C54 C37 106(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C66 1.347(16) .
N C4 1.390(19) .
N C3 1.467(18) .
C3 C10 1.38(2) .
C3 C8 1.40(2) .
C4 C4 1.36(3) 4_565
C4 H4 0.9300 .
C66 N 1.347(16) 4_565
C66 C9 1.52(3) .
C8 C13 1.41(2) .
C8 C18 1.50(2) .
C9 C12 1.54(3) .
C9 C16 1.56(2) 4_565
C9 C16 1.56(2) .
C10 C14 1.37(2) .
C10 C22 1.55(2) .
C11 C12 1.39(2) .
C11 C21 1.41(3) .
C11 C26 1.47(2) .
C12 C11 1.39(2) 4_565
C13 C19 1.37(2) .
C13 H13 0.9300 .
C14 C19 1.40(2) .
C14 H14 0.9300 .
C15 C17 1.39(3) .
C15 C44 1.49(3) .
C15 C44 1.49(3) 4_565
C16 C24 1.40(3) .
C16 C32 1.44(2) .
C17 C20 1.46(2) .
C17 C20 1.46(2) 4_565
C18 C27 1.53(2) .
C18 C42 1.56(2) .
C18 H18 0.97(17) .
C19 H19 0.9300 .
C20 C29 1.36(3) .
C20 C23 1.46(2) .
C21 C24 1.44(3) .
C21 C47 1.44(3) .
C22 C25 1.50(2) .
C22 C48 1.54(3) .
C22 H22 0.99(19) .
C23 C23 1.33(4) 4_565
C23 C41 1.43(3) .
C24 C35 1.42(3) .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C26 C26 1.36(4) 4_565
C26 C37 1.37(3) .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 C38 1.42(4) .
C28 C40 1.43(4) .
C28 C29 1.45(3) .
C29 C39 1.46(3) .
C30 C46 1.30(3) .
C30 C44 1.50(3) .
C30 C30 1.51(6) 4_565
C31 C43 1.40(4) .
C31 C32 1.41(3) .
C31 C36 1.47(3) .
C32 C32 1.43(4) 4_565
C33 C37 1.41(3) .
C33 C41 1.41(3) .
C33 C33 1.44(5) 4_565
C34 C53 1.35(4) .
C34 C38 1.43(4) .
C34 C39 1.45(3) .
C35 C43 1.43(4) .
C35 C50 1.47(3) .
C36 C36 1.35(6) 4_565
C36 C46 1.47(3) .
C37 C54 1.46(4) .
C38 C50 1.39(3) .
C39 C44 1.32(3) .
C40 C41 1.41(4) .
C40 C54 1.45(3) .
C42 H42A 0.9600 .
C42 H42B 0.9600 .
C42 H42C 0.9600 .
C43 C53 1.49(3) .
C46 C53 1.58(4) .
C47 C54 1.40(4) .
C47 C50 1.41(4) .
C48 H48A 0.9600 .
C48 H48B 0.9600 .
C48 H48C 0.9600 .
