#------------------------------------------------------------------------------
#$Date: 2017-11-29 12:25:12 +0200 (Wed, 29 Nov 2017) $
#$Revision: 203789 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/83/1548326.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_1548326
loop_
_publ_author_name
'Yuan-Zhi Tan'
'Bo Yang'
'Khaled Parvez'
'Akimitsu Narita'
'Silvio Osella'
'David Beljonne'
'Xinliang Feng'
'Klaus Mullen'
_publ_section_title
;
 Atomically precise edge chlorination of nanographenes and its application
 in graphene nanoribbons
;
_journal_name_full               'Nature Communications'
_journal_page_first              2646
_journal_paper_doi               10.1038/ncomms3646
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C60 Cl24'
_chemical_formula_sum            'C60 Cl24'
_chemical_formula_weight         1571.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.949(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.4128(7)
_cell_length_b                   22.9777(6)
_cell_length_c                   15.0794(5)
_cell_measurement_temperature    173(2)
_cell_volume                     6689.5(4)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12430
_diffrn_reflns_theta_full        66.49
_diffrn_reflns_theta_max         66.49
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    9.277
_exptl_absorpt_correction_T_max  0.3784
_exptl_absorpt_correction_T_min  0.2347
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                4652
_reflns_number_total             5897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            4.cif
_cod_data_source_block           4
_cod_database_code               1548326
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl10 Cl 0.16016(3) 0.36689(3) 0.95699(4) 0.02615(15) Uani 1 1 d . . .
Cl9 Cl 0.21383(3) 0.48062(3) 1.05147(4) 0.02663(15) Uani 1 1 d . . .
Cl6 Cl 0.31175(4) 0.68242(3) 1.22205(5) 0.03364(17) Uani 1 1 d . . .
Cl7 Cl 0.17085(4) 0.65212(3) 1.24576(4) 0.02901(16) Uani 1 1 d . . .
Cl11 Cl 0.01923(4) 0.32047(3) 0.96270(5) 0.02917(16) Uani 1 1 d . . .
Cl8 Cl 0.11756(4) 0.53651(3) 1.14942(4) 0.02722(16) Uani 1 1 d . . .
Cl4 Cl 0.31223(4) 0.91416(4) 1.23223(6) 0.0403(2) Uani 1 1 d . . .
Cl5 Cl 0.36421(4) 0.79634(4) 1.33200(5) 0.0401(2) Uani 1 1 d . . .
Cl3 Cl 0.21239(4) 0.91117(3) 1.02843(6) 0.03924(19) Uani 1 1 d . . .
Cl1 Cl -0.03649(4) 0.90313(3) 0.82785(5) 0.03307(17) Uani 1 1 d . . .
Cl2 Cl 0.06239(4) 0.89933(3) 1.03006(5) 0.03211(17) Uani 1 1 d . . .
Cl12 Cl -0.00483(4) 0.20324(3) 0.85277(6) 0.03933(19) Uani 1 1 d . . .
C13 C 0.04728(14) 0.42615(12) 0.84280(18) 0.0199(5) Uani 1 1 d . . .
C14 C 0.02450(13) 0.58654(11) 0.79564(18) 0.0194(5) Uani 1 1 d . . .
C15 C 0.11688(14) 0.80005(12) 0.98297(19) 0.0233(6) Uani 1 1 d . . .
C16 C 0.05094(13) 0.63995(12) 0.83955(18) 0.0186(5) Uani 1 1 d . . .
C17 C 0.09947(14) 0.74779(12) 0.93250(18) 0.0212(5) Uani 1 1 d . . .
C18 C 0.11369(13) 0.58733(12) 0.98445(18) 0.0206(5) Uani 1 1 d . . .
C19 C 0.01977(14) 0.80032(12) 0.79963(19) 0.0231(6) Uani 1 1 d . . .
C20 C 0.10866(14) 0.42811(12) 0.92264(18) 0.0215(5) Uani 1 1 d . . .
C21 C 0.20193(15) 0.74719(13) 1.11298(19) 0.0237(6) Uani 1 1 d . . .
C22 C 0.04897(13) 0.53272(12) 0.84182(18) 0.0187(5) Uani 1 1 d . . .
C23 C 0.21938(16) 0.85064(13) 1.0986(2) 0.0278(6) Uani 1 1 d . . .
C24 C 0.01641(13) 0.37181(12) 0.79920(18) 0.0201(5) Uani 1 1 d . . .
C25 C 0.12396(13) 0.69331(12) 0.97859(18) 0.0203(5) Uani 1 1 d . . .
C26 C 0.26541(15) 0.74626(14) 1.1875(2) 0.0280(6) Uani 1 1 d . . .
C27 C 0.00302(15) 0.26730(12) 0.7981(2) 0.0287(6) Uani 1 1 d . . .
C28 C 0.16460(14) 0.69417(12) 1.07432(19) 0.0221(5) Uani 1 1 d . . .
C29 C 0.02481(13) 0.47933(12) 0.79667(18) 0.0194(5) Uani 1 1 d . . .
C30 C 0.02643(13) 0.69315(12) 0.79471(18) 0.0201(5) Uani 1 1 d . . .
C31 C 0.17832(15) 0.80054(13) 1.06715(19) 0.0243(6) Uani 1 1 d . . .
C32 C 0.09822(14) 0.53284(12) 0.93409(18) 0.0206(5) Uani 1 1 d . . .
C33 C 0.27271(15) 0.85015(14) 1.1844(2) 0.0297(7) Uani 1 1 d . . .
C34 C 0.29562(15) 0.79778(15) 1.2288(2) 0.0308(7) Uani 1 1 d . . .
C35 C 0.02375(15) 0.84802(12) 0.8609(2) 0.0246(6) Uani 1 1 d . . .
C36 C 0.13345(13) 0.48016(13) 0.96583(18) 0.0227(6) Uani 1 1 d . . .
C37 C 0.09835(13) 0.64030(12) 0.93395(18) 0.0202(5) Uani 1 1 d . . .
C38 C 0.07039(15) 0.84689(12) 0.9520(2) 0.0251(6) Uani 1 1 d . . .
C39 C 0.13467(14) 0.59260(13) 1.08331(19) 0.0225(6) Uani 1 1 d . . .
C40 C 0.15865(14) 0.64453(13) 1.12701(19) 0.0237(6) Uani 1 1 d . . .
C43 C 0.04960(14) 0.74727(12) 0.84113(19) 0.0200(5) Uani 1 1 d . . .
C44 C 0.01534(14) 0.31904(13) 0.8466(2) 0.0245(6) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C20 C13 C24 122.7(2) . .
C29 C13 C20 116.4(2) . .
C29 C13 C24 119.9(2) . .
C14 C14 C16 119.79(15) 2_556 .
C14 C14 C22 119.96(15) 2_556 .
C16 C14 C22 120.2(2) . .
C17 C15 C31 118.1(3) . .
C17 C15 C38 116.6(2) . .
C38 C15 C31 125.1(3) . .
C14 C16 C37 120.0(2) . .
C30 C16 C14 120.4(2) . .
C30 C16 C37 119.4(2) . .
C15 C17 C25 119.6(2) . .
C15 C17 C43 120.5(3) . .
C43 C17 C25 119.2(3) . .
C37 C18 C32 119.3(2) . .
C37 C18 C39 115.5(2) . .
C39 C18 C32 124.5(3) . .
C35 C19 C19 124.51(18) . 2_556
C43 C19 C19 118.13(17) . 2_556
C43 C19 C35 116.9(2) . .
C13 C20 Cl10 120.5(2) . .
C36 C20 Cl10 118.0(2) . .
C36 C20 C13 120.9(2) . .
C26 C21 C28 122.1(3) . .
C31 C21 C26 118.8(3) . .
C31 C21 C28 118.7(2) . .
C14 C22 C32 119.9(2) . .
C29 C22 C14 120.4(2) . .
C29 C22 C32 119.8(2) . .
C31 C23 Cl3 121.9(2) . .
C33 C23 Cl3 117.4(2) . .
C33 C23 C31 120.3(3) . .
C24 C24 C13 117.47(16) 2_556 .
C44 C24 C13 125.7(2) . .
C44 C24 C24 116.81(17) . 2_556
C28 C25 C17 118.5(3) . .
C37 C25 C17 120.3(2) . .
C37 C25 C28 120.3(3) . .
C21 C26 Cl6 121.5(2) . .
C34 C26 Cl6 118.0(2) . .
C34 C26 C21 120.2(3) . .
C27 C27 Cl12 120.03(12) 2_556 .
C44 C27 Cl12 121.0(2) . .
C44 C27 C27 119.00(18) . 2_556
C25 C28 C21 118.6(3) . .
C25 C28 C40 115.6(2) . .
C40 C28 C21 125.3(2) . .
C13 C29 C22 120.6(2) . .
C13 C29 C29 119.68(15) . 2_556
C22 C29 C29 119.67(15) . 2_556
C16 C30 C30 119.69(15) . 2_556
C16 C30 C43 120.7(2) . .
C30 C30 C43 119.39(15) 2_556 .
C21 C31 C15 118.5(2) . .
C23 C31 C15 123.0(3) . .
C23 C31 C21 118.2(3) . .
C22 C32 C18 118.6(2) . .
C36 C32 C18 124.4(2) . .
C36 C32 C22 116.7(2) . .
C23 C33 Cl4 120.1(3) . .
C34 C33 Cl4 120.2(2) . .
C34 C33 C23 119.7(3) . .
C26 C34 Cl5 120.1(3) . .
C33 C34 Cl5 120.1(2) . .
C33 C34 C26 119.7(3) . .
C19 C35 Cl1 119.7(2) . .
C38 C35 Cl1 119.6(2) . .
C38 C35 C19 120.2(3) . .
C20 C36 Cl9 118.2(2) . .
C20 C36 C32 121.1(2) . .
C32 C36 Cl9 120.3(2) . .
C18 C37 C16 119.2(2) . .
C25 C37 C16 120.3(2) . .
C25 C37 C18 120.2(2) . .
C15 C38 Cl2 120.6(2) . .
C35 C38 Cl2 118.2(2) . .
C35 C38 C15 120.7(3) . .
C18 C39 Cl8 119.6(2) . .
C40 C39 Cl8 118.5(2) . .
C40 C39 C18 121.2(3) . .
C28 C40 Cl7 119.2(2) . .
C39 C40 Cl7 119.5(2) . .
C39 C40 C28 120.8(2) . .
C17 C43 C30 120.0(2) . .
C19 C43 C17 119.4(3) . .
C19 C43 C30 120.4(2) . .
C24 C44 Cl11 119.6(2) . .
C27 C44 Cl11 119.7(2) . .
C27 C44 C24 120.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl10 C20 1.731(3) .
Cl9 C36 1.727(3) .
Cl6 C26 1.731(3) .
Cl7 C40 1.735(3) .
Cl11 C44 1.726(3) .
Cl8 C39 1.733(3) .
Cl4 C33 1.719(3) .
Cl5 C34 1.723(3) .
Cl3 C23 1.726(3) .
Cl1 C35 1.722(3) .
Cl2 C38 1.729(3) .
Cl12 C27 1.719(3) .
C13 C20 1.429(4) .
C13 C24 1.456(4) .
C13 C29 1.407(4) .
C14 C14 1.415(5) 2_556
C14 C16 1.415(4) .
C14 C22 1.427(4) .
C15 C17 1.404(4) .
C15 C31 1.466(4) .
C15 C38 1.410(4) .
C16 C30 1.408(4) .
C16 C37 1.438(4) .
C17 C25 1.440(4) .
C17 C43 1.423(4) .
C18 C32 1.445(4) .
C18 C37 1.416(4) .
C18 C39 1.416(4) .
C19 C19 1.452(5) 2_556
C19 C35 1.419(4) .
C19 C43 1.415(4) .
C20 C36 1.377(4) .
C21 C26 1.413(4) .
C21 C28 1.455(4) .
C21 C31 1.413(4) .
C22 C29 1.412(4) .
C22 C32 1.428(4) .
C23 C31 1.412(4) .
C23 C33 1.394(4) .
C24 C24 1.416(5) 2_556
C24 C44 1.411(4) .
C25 C28 1.412(4) .
C25 C37 1.408(4) .
C26 C34 1.386(4) .
C27 C27 1.417(6) 2_556
C27 C44 1.375(4) .
C28 C40 1.418(4) .
C29 C29 1.443(5) 2_556
C30 C30 1.428(5) 2_556
C30 C43 1.430(4) .
C32 C36 1.410(4) .
C33 C34 1.382(5) .
C35 C38 1.395(4) .
C39 C40 1.374(4) .
