#------------------------------------------------------------------------------
#$Date: 2017-09-11 17:12:43 +0300 (Mon, 11 Sep 2017) $
#$Revision: 200466 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/28/4032819.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_4032819
loop_
_publ_author_name
'Li, Zong-Jun'
'Wang, Sisi'
'Li, Shu-Hui'
'Sun, Tao'
'Yang, Wei-Wei'
'Shoyama, Kazutaka'
'Nakagawa, Takafumi'
'Jeon, Il'
'Yang, Xiaoniu'
'Matsuo, Yutaka'
'Gao, Xiang'
_publ_section_title
;
 Regiocontrolled Electrosynthesis of [60]Fullerene Bisadducts:
 Photovoltaic Performance and Crystal Structures of C60 o-Quinodimethane
 Bisadducts.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8676
_journal_page_last               8685
_journal_paper_doi               10.1021/acs.joc.7b01732
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C39 H9 Cl3'
_chemical_formula_sum            'C39 H9 Cl3'
_chemical_formula_weight         583.81
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 100.0560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.3397(19)
_cell_length_b                   10.2812(9)
_cell_length_c                   20.0732(17)
_cell_measurement_reflns_used    2352
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.85
_cell_volume                     4539.6(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      188(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13778
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2352
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0782P)²+4.4465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                3301
_reflns_number_total             4457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01732_si_002.cif
_cod_data_source_block           lzj_trans3_C60(QM)2
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4032819
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl1 Cl 0.19954(4) 0.05926(10) 0.07713(4) 0.0530(3) Uani 1 1 d
Cl2 Cl 0.09329(5) -0.10484(10) 0.05781(5) 0.0623(3) Uani 1 1 d
Cl3 Cl 0.09639(6) 0.12150(11) -0.02546(5) 0.0735(4) Uani 1 1 d
C77 C 0.13931(17) -0.0029(3) 0.01768(16) 0.0418(8) Uani 1 1 d
C9 C 0.15796(11) 0.4205(3) 0.24644(14) 0.0246(6) Uani 1 1 d
C14 C 0.02947(12) 0.0873(2) 0.24291(14) 0.0233(6) Uani 1 1 d
C5 C 0.10268(11) 0.2837(3) 0.38606(12) 0.0217(6) Uani 1 1 d
C21 C 0.10154(12) 0.5582(3) 0.38612(14) 0.0276(6) Uani 1 1 d
C3 C 0.08021(12) 0.1268(3) 0.29259(14) 0.0238(6) Uani 1 1 d
C12 C 0.09642(12) 0.1962(3) 0.18550(13) 0.0246(6) Uani 1 1 d
C63 C 0.21993(14) -0.0791(3) 0.36057(16) 0.0327(7) Uani 1 1 d
C10 C 0.13352(12) 0.4207(3) 0.17922(14) 0.0268(6) Uani 1 1 d
C28 C 0.05104(12) 0.3490(3) 0.09822(13) 0.0280(6) Uani 1 1 d
C38 C 0.00327(13) 0.5582(3) 0.41178(14) 0.0314(7) Uani 1 1 d
C26 C 0.10165(12) 0.5336(3) 0.14797(14) 0.0303(7) Uani 1 1 d
C20 C 0.06064(12) 0.4883(3) 0.42128(13) 0.0278(6) Uani 1 1 d
C1 C 0.16702(11) 0.2986(3) 0.29107(13) 0.0232(6) Uani 1 1 d
C23 C 0.07984(13) 0.7148(3) 0.29222(16) 0.0328(7) Uani 1 1 d
C7 C 0.14046(11) 0.4888(3) 0.35221(13) 0.0254(6) Uani 1 1 d
C13 C 0.03950(12) 0.1291(3) 0.17719(14) 0.0247(6) Uani 1 1 d
C11 C 0.10189(12) 0.3039(3) 0.14758(13) 0.0269(6) Uani 1 1 d
C42 C 0.02929(13) 0.7589(3) 0.24264(16) 0.0340(7) Uani 1 1 d
C22 C 0.07010(13) 0.6728(3) 0.35497(15) 0.0321(7) Uani 1 1 d
C6 C 0.14208(11) 0.3504(3) 0.35319(13) 0.0223(6) Uani 1 1 d
C8 C 0.15050(11) 0.5329(3) 0.28613(14) 0.0264(6) Uani 1 1 d
C24 C 0.12116(12) 0.6441(3) 0.25757(15) 0.0299(7) Uani 1 1 d
C27 C 0.05120(13) 0.4898(3) 0.09796(13) 0.0310(7) Uani 1 1 d
C29 C -0.00416(12) 0.2824(3) 0.08903(12) 0.0265(6) Uani 1 1 d
C19 C 0.06088(12) 0.3533(3) 0.42055(13) 0.0256(6) Uani 1 1 d
C68 C 0.23635(12) 0.2687(3) 0.31261(15) 0.0284(6) Uani 1 1 d
C62 C 0.21498(12) 0.0373(3) 0.32564(14) 0.0271(6) Uani 1 1 d
C25 C 0.09632(13) 0.6449(3) 0.18621(15) 0.0323(7) Uani 1 1 d
C67 C 0.24528(11) 0.1476(3) 0.35466(14) 0.0269(6) Uani 1 1 d
C43 C 0.03947(13) 0.7158(3) 0.17649(16) 0.0338(7) Uani 1 1 d
C4 C 0.07107(12) 0.1673(3) 0.35469(13) 0.0229(6) Uani 1 1 d
C30 C -0.00996(12) 0.1694(3) 0.12928(13) 0.0254(6) Uani 1 1 d
C65 C 0.28572(15) 0.0233(4) 0.45381(17) 0.0387(8) Uani 1 1 d
C2 C 0.13220(11) 0.1722(3) 0.25735(13) 0.0230(6) Uani 1 1 d
C39 C 0.00933(13) 0.6730(3) 0.37126(15) 0.0329(7) Uani 1 1 d
C66 C 0.27977(13) 0.1405(3) 0.41903(16) 0.0335(7) Uani 1 1 d
C61 C 0.17760(13) 0.0569(3) 0.25667(15) 0.0292(6) Uani 1 1 d
C64 C 0.25591(14) -0.0865(3) 0.42455(17) 0.0379(8) Uani 1 1 d
H9 H 0.1608(14) -0.055(3) -0.0140(16) 0.035(8) Uiso 1 1 d
H1 H 0.2562(12) 0.347(3) 0.3382(14) 0.022(7) Uiso 1 1 d
H3 H 0.3003(13) 0.219(3) 0.4385(14) 0.027(7) Uiso 1 1 d
H2 H 0.2543(13) 0.260(3) 0.2698(15) 0.028(8) Uiso 1 1 d
H8 H 0.1547(14) -0.020(3) 0.2425(15) 0.034(8) Uiso 1 1 d
H7 H 0.2044(15) 0.075(3) 0.2218(17) 0.044(9) Uiso 1 1 d
H6 H 0.1981(14) -0.149(3) 0.3410(16) 0.033(9) Uiso 1 1 d
H4 H 0.3099(16) 0.017(3) 0.4947(18) 0.049(10) Uiso 1 1 d
H5 H 0.2618(15) -0.168(4) 0.4495(18) 0.048(10) Uiso 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'
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
Cl3 C77 Cl1 111.2(2) . .
Cl3 C77 Cl2 110.6(2) . .
Cl1 C77 Cl2 110.22(17) . .
C10 C9 C8 119.0(3) . .
C10 C9 C1 124.6(3) . .
C8 C9 C1 110.6(2) . .
C14 C14 C3 121.2(3) 2 .
C14 C14 C13 119.3(3) 2 .
C3 C14 C13 108.8(2) . .
C6 C5 C19 120.4(3) . .
C6 C5 C4 120.0(2) . .
C19 C5 C4 107.8(2) . .
C7 C21 C20 119.2(3) . .
C7 C21 C22 120.1(3) . .
C20 C21 C22 108.3(2) . .
C4 C3 C14 119.8(2) . .
C4 C3 C2 125.1(2) . .
C14 C3 C2 109.6(2) . .
C11 C12 C13 119.5(3) . .
C11 C12 C2 124.8(2) . .
C13 C12 C2 109.7(2) . .
C62 C63 C64 119.8(3) . .
C9 C10 C26 120.8(3) . .
C9 C10 C11 120.1(3) . .
C26 C10 C11 107.6(2) . .
C29 C28 C27 119.6(3) . .
C29 C28 C11 120.2(3) . .
C27 C28 C11 108.7(2) . .
C27 C38 C20 119.9(3) 2 .
C27 C38 C39 119.8(3) 2 .
C20 C38 C39 108.0(2) . .
C25 C26 C27 120.5(3) . .
C25 C26 C10 120.2(3) . .
C27 C26 C10 108.5(3) . .
C19 C20 C21 119.3(2) . .
C19 C20 C38 119.9(3) . .
C21 C20 C38 108.0(3) . .
C9 C1 C6 99.2(2) . .
C9 C1 C68 110.2(2) . .
C6 C1 C68 108.9(2) . .
C9 C1 C2 114.3(2) . .
C6 C1 C2 113.8(2) . .
C68 C1 C2 110.0(2) . .
C22 C23 C42 119.8(3) . .
C22 C23 C24 119.8(3) . .
C42 C23 C24 108.4(3) . .
C21 C7 C6 121.5(2) . .
C21 C7 C8 119.7(3) . .
C6 C7 C8 108.4(2) . .
C30 C13 C12 121.2(3) . .
C30 C13 C14 119.2(2) . .
C12 C13 C14 108.3(2) . .
C12 C11 C28 120.5(3) . .
C12 C11 C10 120.2(2) . .
C28 C11 C10 107.0(3) . .
C42 C42 C23 120.4(4) 2 .
C42 C42 C43 119.8(3) 2 .
C23 C42 C43 107.8(3) . .
C23 C22 C39 120.4(3) . .
C23 C22 C21 120.2(3) . .
C39 C22 C21 107.7(3) . .
C5 C6 C7 119.3(2) . .
C5 C6 C1 124.5(2) . .
C7 C6 C1 110.2(2) . .
C24 C8 C9 121.8(3) . .
C24 C8 C7 119.7(3) . .
C9 C8 C7 107.9(2) . .
C8 C24 C25 119.0(3) . .
C8 C24 C23 120.6(3) . .
C25 C24 C23 107.9(3) . .
C38 C27 C26 119.9(3) 2 .
C38 C27 C28 120.3(3) 2 .
C26 C27 C28 108.2(2) . .
C28 C29 C30 119.2(2) . .
C28 C29 C19 120.3(3) . 2
C30 C29 C19 108.7(2) . 2
C20 C19 C5 120.3(2) . .
C20 C19 C29 120.1(3) . 2
C5 C19 C29 108.1(2) . 2
C67 C68 C1 110.3(2) . .
C63 C62 C67 120.2(3) . .
C63 C62 C61 124.5(3) . .
C67 C62 C61 115.3(3) . .
C26 C25 C24 119.1(3) . .
C26 C25 C43 119.8(3) . .
C24 C25 C43 108.2(3) . .
C66 C67 C62 119.8(3) . .
C66 C67 C68 124.5(3) . .
C62 C67 C68 115.7(2) . .
C39 C43 C25 119.8(3) 2 .
C39 C43 C42 119.8(3) 2 .
C25 C43 C42 107.7(3) . .
C3 C4 C30 120.2(2) . 2
C3 C4 C5 120.1(2) . .
C30 C4 C5 106.9(2) 2 .
C13 C30 C29 119.4(2) . .
C13 C30 C4 120.2(2) . 2
C29 C30 C4 108.5(2) . 2
C66 C65 C64 119.8(3) . .
C3 C2 C12 99.8(2) . .
C3 C2 C61 108.5(2) . .
C12 C2 C61 110.1(2) . .
C3 C2 C1 113.7(2) . .
C12 C2 C1 113.6(2) . .
C61 C2 C1 110.6(2) . .
C43 C39 C22 119.8(3) 2 .
C43 C39 C38 120.3(3) 2 .
C22 C39 C38 107.9(3) . .
C67 C66 C65 120.3(3) . .
C62 C61 C2 110.6(2) . .
C65 C64 C63 120.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C77 1.756(4) .
Cl2 C77 1.759(4) .
Cl3 C77 1.737(3) .
C9 C10 1.364(4) .
C9 C8 1.430(4) .
C9 C1 1.533(4) .
C14 C14 1.395(5) 2
C14 C3 1.432(4) .
C14 C13 1.442(4) .
C5 C6 1.372(4) .
C5 C19 1.445(4) .
C5 C4 1.474(4) .
C21 C7 1.391(4) .
C21 C20 1.440(4) .
C21 C22 1.455(4) .
C3 C4 1.363(4) .
C3 C2 1.534(4) .
C12 C11 1.361(4) .
C12 C13 1.431(4) .
C12 C2 1.542(4) .
C63 C62 1.381(4) .
C63 C64 1.393(5) .
C10 C26 1.446(4) .
C10 C11 1.479(4) .
C28 C29 1.395(4) .
C28 C27 1.447(4) .
C28 C11 1.447(4) .
C38 C27 1.389(4) 2
C38 C20 1.453(4) .
C38 C39 1.454(4) .
C26 C25 1.395(4) .
C26 C27 1.444(4) .
C20 C19 1.388(4) .
C1 C6 1.547(4) .
C1 C68 1.564(4) .
C1 C2 1.602(4) .
C23 C22 1.384(4) .
C23 C42 1.442(4) .
C23 C24 1.445(4) .
C7 C6 1.423(4) .
C7 C8 1.456(4) .
C13 C30 1.395(4) .
C42 C42 1.391(6) 2
C42 C43 1.455(5) .
C22 C39 1.451(4) .
C8 C24 1.391(4) .
C24 C25 1.443(4) .
C27 C38 1.389(4) 2
C29 C30 1.433(4) .
C29 C19 1.445(4) 2
C19 C29 1.445(4) 2
C68 C67 1.498(4) .
C62 C67 1.395(4) .
C62 C61 1.500(4) .
C25 C43 1.448(4) .
C67 C66 1.386(4) .
C43 C39 1.391(4) 2
C4 C30 1.456(4) 2
C30 C4 1.456(4) 2
C65 C66 1.387(5) .
C65 C64 1.388(5) .
C2 C61 1.562(4) .
C39 C43 1.391(4) 2
