#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:58:16 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/47/1554725.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_1554725
loop_
_publ_author_name
'Ma, Yue'
'Uchiyama, Kouya'
'Ueno, Hiroshi'
'Okada, Hiroshi'
'Moriyama, Hiroshi'
'Matsuo, Yutaka'
_publ_section_title
;
 Highly soluble C2v-symmetrical fullerene derivatives: efficient
 synthesis, characterization, and electrochemical study
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1372
_journal_paper_doi               10.1039/C9QO00056A
_journal_volume                  6
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C76 H32 F8 O8'
_chemical_formula_sum            'C76 H32 F8 O8'
_chemical_formula_weight         1225.02
_chemical_name_systematic
;
 C60(OCH2CH2F)8
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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_date             2018-12-15T16:08:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-12-15 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.518(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.035(12)
_cell_length_b                   15.426(7)
_cell_length_c                   17.593(10)
_cell_measurement_reflns_used    7644
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      3.091
_cell_measurement_wavelength     0.71073
_cell_volume                     5098(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.2085
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5754
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2496
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0915
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0162P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                3565
_reflns_number_total             5754
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c9qo00056a2.cif
_cod_data_source_block           octaF8
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1554725
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
_atom_site_refinement_flags
C1 C 0.9104(2) 0.9532(2) 0.2499(3) 0.0194(9) Uani 1 1 d .
C2 C 0.9649(2) 0.9321(2) 0.2218(3) 0.0182(8) Uani 1 1 d .
C3 C 0.9297(2) 0.9521(2) 0.1214(3) 0.0197(9) Uani 1 1 d .
C4 C 0.8621(2) 1.0176(2) 0.1781(3) 0.0189(8) Uani 1 1 d .
C5 C 0.8704(2) 1.0173(3) 0.1079(3) 0.0203(9) Uani 1 1 d .
C6 C 0.8181(2) 1.0848(3) 0.1925(3) 0.0203(9) Uani 1 1 d .
C7 C 0.8384(2) 1.0857(3) 0.0336(3) 0.0188(9) Uani 1 1 d .
C8 C 0.9804(2) 0.9991(3) 0.1032(3) 0.0215(9) Uani 1 1 d .
C9 C 1.0529(2) 0.9992(3) 0.1609(3) 0.0199(9) Uani 1 1 d .
C10 C 0.9176(2) 1.0772(3) 0.3557(3) 0.0208(9) Uani 1 1 d .
C11 C 0.8609(2) 1.1209(3) 0.2883(3) 0.0188(8) Uani 1 1 d .
C12 C 0.81094(19) 1.1678(3) 0.1390(3) 0.0188(8) Uani 1 1 d .
C13 C 0.8211(2) 1.1670(3) 0.0686(3) 0.0188(9) Uani 1 1 d .
C14 C 0.8964(2) 1.1204(3) 0.0188(3) 0.0204(9) Uani 1 1 d .
C15 C 0.9594(2) 1.0772(3) 0.0463(2) 0.0197(9) Uani 1 1 d .
C16 C 0.8616(2) 1.2144(3) 0.2876(3) 0.0206(9) Uani 1 1 d .
C17 C 0.8312(2) 1.2430(3) 0.1958(3) 0.0219(9) Uani 1 1 d .
C18 C 0.8506(2) 1.2434(3) 0.0503(3) 0.0201(9) Uani 1 1 d .
C19 C 0.8976(2) 1.2146(2) 0.0211(3) 0.0192(9) Uani 1 1 d .
C20 C 1.0247(2) 1.1236(3) 0.0718(3) 0.0210(9) Uani 1 1 d .
C21 C 0.9162(2) 1.2613(3) 0.3570(3) 0.0208(9) Uani 1 1 d .
C22 C 0.8579(2) 1.3168(3) 0.1785(3) 0.0201(9) Uani 1 1 d .
C23 C 0.8686(2) 1.3175(3) 0.1036(3) 0.0215(9) Uani 1 1 d .
C24 C 0.9594(2) 1.2611(3) 0.0441(3) 0.0231(9) Uani 1 1 d .
C25 C 1.0242(2) 1.2138(3) 0.0701(3) 0.0213(9) Uani 1 1 d .
C26 C 0.9463(2) 1.3375(3) 0.3391(3) 0.0266(10) Uani 1 1 d .
C27 C 0.9164(2) 1.3652(3) 0.2504(3) 0.0229(9) Uani 1 1 d .
C28 C 0.9332(2) 1.3655(3) 0.1292(3) 0.0237(10) Uani 1 1 d .
C29 C 0.9777(2) 1.3377(3) 0.1007(3) 0.0222(9) Uani 1 1 d .
C30 C 0.9637(2) 1.3945(3) 0.2211(3) 0.0246(9) Uani 1 1 d .
C31 C 0.9046(2) 0.8158(3) 0.3114(3) 0.0249(10) Uani 1 1 d .
H31A H 0.9243 0.8399 0.3707 0.03 Uiso 1 1 calc R
H31B H 0.9436 0.7933 0.3064 0.03 Uiso 1 1 calc R
C32 C 0.8540(3) 0.7455(3) 0.2964(4) 0.0444(13) Uani 1 1 d .
H32A H 0.8311 0.7255 0.2353 0.053 Uiso 1 1 calc R
H32B H 0.8794 0.6971 0.3354 0.053 Uiso 1 1 calc R
C33 C 0.8616(2) 0.8172(3) 0.0729(3) 0.0275(10) Uani 1 1 d .
H33A H 0.8173 0.8441 0.0597 0.033 Uiso 1 1 calc R
H33B H 0.886 0.7958 0.1336 0.033 Uiso 1 1 calc R
C34 C 0.8471(3) 0.7444(3) 0.0092(3) 0.0379(12) Uani 1 1 d .
H34A H 0.8103 0.707 0.0056 0.045 Uiso 1 1 calc R
H34B H 0.8306 0.7673 -0.0498 0.045 Uiso 1 1 calc R
C35 C 0.7023(2) 1.0232(3) 0.0890(3) 0.0294(10) Uani 1 1 d .
H35A H 0.7241 0.9813 0.0694 0.035 Uiso 1 1 calc R
H35B H 0.6876 1.0729 0.0494 0.035 Uiso 1 1 calc R
C36 C 0.6401(2) 0.9842(3) 0.0860(3) 0.0316(11) Uani 1 1 d .
H36A H 0.6083 0.9605 0.0271 0.038 Uiso 1 1 calc R
H36B H 0.6557 0.9371 0.1287 0.038 Uiso 1 1 calc R
C37 C 0.7843(2) 1.0037(3) -0.1044(3) 0.0233(9) Uani 1 1 d .
H37A H 0.8244 0.9648 -0.071 0.028 Uiso 1 1 calc R
H37B H 0.7939 1.0399 -0.142 0.028 Uiso 1 1 calc R
C38 C 0.7175(2) 0.9528(3) -0.1601(3) 0.0266(10) Uani 1 1 d .
H38A H 0.6767 0.9913 -0.1846 0.032 Uiso 1 1 calc R
H38B H 0.7184 0.926 -0.2094 0.032 Uiso 1 1 calc R
O1 O 0.86731(14) 0.88131(17) 0.24582(18) 0.0220(6) Uani 1 1 d .
O2 O 0.90497(14) 0.87837(17) 0.06241(17) 0.0199(6) Uani 1 1 d .
O3 O 0.75265(15) 1.04981(18) 0.17875(18) 0.0231(7) Uani 1 1 d .
O4 O 0.77424(15) 1.05649(18) -0.04447(18) 0.0225(7) Uani 1 1 d .
F1 F 0.80358(18) 0.7750(3) 0.3133(2) 0.0786(13) Uani 1 1 d .
F2 F 0.91027(19) 0.69694(19) 0.0399(2) 0.0572(9) Uani 1 1 d .
F3 F 0.60406(15) 1.0449(2) 0.1055(2) 0.0566(10) Uani 1 1 d .
F4 F 0.71107(16) 0.88841(19) -0.10820(19) 0.0472(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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O1 C1 C9 113.2(3) . 2_755
O1 C1 C4 107.8(3) . .
C9 C1 C4 108.5(3) 2_755 .
O1 C1 C2 115.0(3) . .
C9 C1 C2 110.2(3) 2_755 .
C4 C1 C2 101.1(3) . .
C2 C2 C3 123.2(4) 2_755 .
C2 C2 C1 123.5(4) 2_755 .
C3 C2 C1 108.2(3) . .
O2 C3 C8 105.7(3) . .
O2 C3 C2 116.1(3) . .
C8 C3 C2 110.8(3) . .
O2 C3 C5 115.3(3) . .
C8 C3 C5 108.3(3) . .
C2 C3 C5 100.5(3) . .
C5 C4 C1 113.0(4) . .
C5 C4 C6 124.0(4) . .
C1 C4 C6 122.3(3) . .
C4 C5 C7 124.1(4) . .
C4 C5 C3 111.6(3) . .
C7 C5 C3 123.1(3) . .
O3 C6 C4 112.7(3) . .
O3 C6 C11 107.8(3) . .
C4 C6 C11 110.4(3) . .
O3 C6 C12 115.7(3) . .
C4 C6 C12 109.4(3) . .
C11 C6 C12 100.1(3) . .
O4 C7 C14 116.1(3) . .
O4 C7 C13 108.3(3) . .
C14 C7 C13 100.8(3) . .
O4 C7 C5 112.6(3) . .
C14 C7 C5 109.5(3) . .
C13 C7 C5 108.7(3) . .
C9 C8 C15 109.4(3) . .
C9 C8 C3 123.5(4) . .
C15 C8 C3 122.2(4) . .
C8 C9 C10 108.6(3) . 2_755
C8 C9 C1 123.3(4) . 2_755
C10 C9 C1 122.5(3) 2_755 2_755
C11 C10 C20 120.5(4) . 2_755
C11 C10 C9 122.1(4) . 2_755
C20 C10 C9 107.8(3) 2_755 2_755
C10 C11 C16 119.4(4) . .
C10 C11 C6 121.9(4) . .
C16 C11 C6 110.8(3) . .
C13 C12 C17 119.8(4) . .
C13 C12 C6 122.0(4) . .
C17 C12 C6 110.4(3) . .
C12 C13 C18 119.7(4) . .
C12 C13 C7 124.3(4) . .
C18 C13 C7 109.8(3) . .
C15 C14 C19 118.3(4) . .
C15 C14 C7 123.2(4) . .
C19 C14 C7 110.5(3) . .
C14 C15 C20 121.5(4) . .
C14 C15 C8 122.3(4) . .
C20 C15 C8 106.4(3) . .
C21 C16 C11 121.5(4) . .
C21 C16 C17 120.2(4) . .
C11 C16 C17 108.2(3) . .
C22 C17 C12 121.4(4) . .
C22 C17 C16 119.4(4) . .
C12 C17 C16 108.8(3) . .
C23 C18 C19 119.0(4) . .
C23 C18 C13 120.9(4) . .
C19 C18 C13 108.4(3) . .
C24 C19 C18 120.6(4) . .
C24 C19 C14 121.4(4) . .
C18 C19 C14 108.1(3) . .
C25 C20 C10 120.7(4) . 2_755
C25 C20 C15 119.5(4) . .
C10 C20 C15 107.7(3) 2_755 .
C16 C21 C25 118.5(4) . 2_755
C16 C21 C26 120.7(4) . .
C25 C21 C26 106.9(4) 2_755 .
C17 C22 C27 121.0(4) . .
C17 C22 C23 119.6(4) . .
C27 C22 C23 107.1(4) . .
C18 C23 C28 120.9(4) . .
C18 C23 C22 118.6(4) . .
C28 C23 C22 108.6(4) . .
C19 C24 C25 118.8(4) . .
C19 C24 C29 119.5(4) . .
C25 C24 C29 108.5(4) . .
C20 C25 C24 120.4(4) . .
C20 C25 C21 119.2(4) . 2_755
C24 C25 C21 108.0(4) . 2_755
C27 C26 C29 120.5(4) . 2_755
C27 C26 C21 118.8(4) . .
C29 C26 C21 109.1(4) 2_755 .
C26 C27 C22 119.8(4) . .
C26 C27 C30 118.7(4) . .
C22 C27 C30 108.9(4) . .
C29 C28 C23 119.7(4) . .
C29 C28 C30 119.6(4) . .
C23 C28 C30 108.0(4) . .
C28 C29 C26 120.4(4) . 2_755
C28 C29 C24 120.2(4) . .
C26 C29 C24 107.5(4) 2_755 .
C30 C30 C27 120.6(5) 2_755 .
C30 C30 C28 120.2(5) 2_755 .
C27 C30 C28 107.3(4) . .
O1 C31 C32 108.2(4) . .
F1 C32 C31 110.0(4) . .
O2 C33 C34 107.3(3) . .
F2 C34 C33 108.7(4) . .
O3 C35 C36 109.0(4) . .
F3 C36 C35 111.1(4) . .
O4 C37 C38 107.5(3) . .
F4 C38 C37 110.1(3) . .
C31 O1 C1 114.8(3) . .
C33 O2 C3 117.2(3) . .
C35 O3 C6 115.0(3) . .
C7 O4 C37 115.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.437(5) .
C1 C9 1.515(5) 2_755
C1 C4 1.520(5) .
C1 C2 1.554(5) .
C2 C2 1.331(8) 2_755
C2 C3 1.543(6) .
C3 O2 1.442(4) .
C3 C8 1.500(5) .
C3 C5 1.566(5) .
C4 C5 1.338(5) .
C4 C6 1.528(5) .
C5 C7 1.535(5) .
C6 O3 1.437(5) .
C6 C11 1.543(6) .
C6 C12 1.547(5) .
C7 O4 1.434(5) .
C7 C14 1.530(5) .
C7 C13 1.531(5) .
C8 C9 1.374(6) .
C8 C15 1.477(5) .
C9 C10 1.467(5) 2_755
C9 C1 1.515(5) 2_755
C10 C11 1.368(5) .
C10 C20 1.436(6) 2_755
C10 C9 1.467(5) 2_755
C11 C16 1.442(5) .
C12 C13 1.368(5) .
C12 C17 1.442(5) .
C13 C18 1.462(6) .
C14 C15 1.379(5) .
C14 C19 1.453(5) .
C15 C20 1.453(6) .
C16 C21 1.387(6) .
C16 C17 1.456(6) .
C17 C22 1.386(5) .
C18 C23 1.398(5) .
C18 C19 1.445(5) .
C19 C24 1.399(5) .
C20 C25 1.391(6) .
C20 C10 1.436(6) 2_755
C21 C25 1.465(5) 2_755
C21 C26 1.464(6) .
C22 C27 1.455(6) .
C22 C23 1.455(6) .
C23 C28 1.451(6) .
C24 C25 1.449(6) .
C24 C29 1.458(6) .
C25 C21 1.465(5) 2_755
C26 C27 1.406(6) .
C26 C29 1.439(6) 2_755
C27 C30 1.454(6) .
C28 C29 1.383(6) .
C28 C30 1.460(6) .
C29 C26 1.439(6) 2_755
C30 C30 1.377(8) 2_755
C31 O1 1.427(5) .
C31 C32 1.478(6) .
C32 F1 1.368(6) .
C33 O2 1.421(4) .
C33 C34 1.498(6) .
C34 F2 1.408(6) .
C35 O3 1.435(5) .
C35 C36 1.473(6) .
C36 F3 1.382(5) .
C37 O4 1.439(5) .
C37 C38 1.495(6) .
C38 F4 1.406(5) .
