#------------------------------------------------------------------------------
#$Date: 2017-11-29 12:24:48 +0200 (Wed, 29 Nov 2017) $
#$Revision: 203787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/83/1548324.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_1548324
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         'C48 Cl18'
_chemical_formula_sum            'C48 Cl18'
_chemical_formula_weight         1214.58
_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                 97.155(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.861(2)
_cell_length_b                   28.435(4)
_cell_length_c                   10.629(3)
_cell_measurement_temperature    173(2)
_cell_volume                     3856.8(14)
_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 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9190
_diffrn_reflns_theta_full        64.99
_diffrn_reflns_theta_max         64.99
_diffrn_reflns_theta_min         3.80
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    12.097
_exptl_absorpt_correction_T_max  0.4090
_exptl_absorpt_correction_T_min  0.2641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.751
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0825
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1717P)²+13.0550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2390
_refine_ls_wR_factor_ref         0.2542
_reflns_number_gt                2510
_reflns_number_total             3161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            2.cif
_cod_data_source_block           2
_cod_original_cell_volume        3856.7(13)
_cod_database_code               1548324
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
Cl1 Cl 0.04028(14) 0.06062(6) 0.08741(19) 0.0402(5) Uani 1 1 d . . .
Cl2 Cl 0.12388(14) -0.14458(5) -0.13631(18) 0.0370(5) Uani 1 1 d . . .
Cl3 Cl 0.22540(14) -0.11742(5) 0.13437(17) 0.0361(5) Uani 1 1 d . . .
Cl4 Cl 0.12610(14) -0.02827(5) 0.21670(17) 0.0368(5) Uani 1 1 d . . .
Cl5 Cl 0.12255(16) 0.15158(6) -0.0006(2) 0.0472(6) Uani 1 1 d . . .
Cl6 Cl 0.53425(15) 0.19013(5) -0.10852(19) 0.0442(6) Uani 1 1 d . . .
Cl7 Cl 0.41132(17) -0.29183(5) -0.1699(2) 0.0487(6) Uani 1 1 d . . .
Cl8 Cl 0.33162(16) 0.19890(5) 0.0055(2) 0.0467(6) Uani 1 1 d . . .
Cl9 Cl 0.20791(16) -0.23822(5) -0.2094(2) 0.0460(6) Uani 1 1 d . . .
C1 C 0.2962(6) -0.0677(2) -0.0572(7) 0.0286(15) Uani 1 1 d . . .
C2 C 0.2568(6) -0.1507(2) -0.1389(7) 0.0305(16) Uani 1 1 d . . .
C3 C 0.4599(6) 0.0184(2) -0.2108(7) 0.0306(16) Uani 1 1 d . . .
C4 C 0.3009(6) 0.0183(2) -0.0454(7) 0.0307(16) Uani 1 1 d . . .
C5 C 0.3586(6) 0.1463(2) -0.0648(7) 0.0343(17) Uani 1 1 d . . .
C6 C 0.1961(6) -0.0255(2) 0.0873(7) 0.0294(15) Uani 1 1 d . . .
C7 C 0.3383(6) -0.0247(2) -0.0914(7) 0.0304(16) Uani 1 1 d . . .
C8 C 0.4102(6) -0.1104(2) -0.1846(7) 0.0314(16) Uani 1 1 d . . .
C9 C 0.2034(6) 0.1030(2) 0.0033(7) 0.0351(17) Uani 1 1 d . . .
C10 C 0.4226(6) 0.0617(2) -0.1650(6) 0.0290(15) Uani 1 1 d . . .
C11 C 0.4573(6) -0.0675(2) -0.2124(6) 0.0291(16) Uani 1 1 d . . .
C12 C 0.4178(6) -0.0246(2) -0.1731(6) 0.0283(15) Uani 1 1 d . . .
C13 C 0.2189(6) 0.0180(2) 0.0322(7) 0.0308(15) Uani 1 1 d . . .
C14 C 0.2948(6) -0.1928(2) -0.1748(7) 0.0344(17) Uani 1 1 d . . .
C15 C 0.3416(6) 0.0620(2) -0.0842(7) 0.0293(15) Uani 1 1 d . . .
C16 C 0.2366(6) -0.0668(2) 0.0470(7) 0.0316(16) Uani 1 1 d . . .
C17 C 0.4520(6) -0.1540(2) -0.2235(7) 0.0348(17) Uani 1 1 d . . .
C18 C 0.3207(6) -0.1101(2) -0.1215(7) 0.0319(16) Uani 1 1 d . . .
C19 C 0.4544(6) -0.2387(2) -0.2226(8) 0.0399(19) Uani 1 1 d . . .
C20 C 0.4663(5) 0.1045(2) -0.2009(7) 0.0320(16) Uani 1 1 d . . .
C21 C 0.1652(5) 0.0610(2) 0.0438(7) 0.0307(15) Uani 1 1 d . . .
C22 C 0.3005(6) 0.1049(2) -0.0459(8) 0.0376(18) Uani 1 1 d . . .
C23 C 0.4018(6) -0.1965(2) -0.1997(7) 0.0376(18) Uani 1 1 d . . .
C24 C 0.4445(6) 0.1452(2) -0.1288(8) 0.0357(17) 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
C7 C1 C16 116.6(6) . .
C7 C1 C18 119.5(6) . .
C16 C1 C18 123.8(6) . .
C14 C2 Cl2 119.0(5) . .
C14 C2 C18 121.9(7) . .
C18 C2 Cl2 118.5(5) . .
C3 C3 C10 120.3(4) 2_654 .
C3 C3 C12 120.2(4) 2_654 .
C12 C3 C10 119.5(6) . .
C7 C4 C15 119.8(6) . .
C13 C4 C7 120.2(6) . .
C13 C4 C15 119.9(6) . .
C22 C5 Cl8 121.2(5) . .
C24 C5 Cl8 116.9(5) . .
C24 C5 C22 121.6(6) . .
C13 C6 Cl4 121.5(5) . .
C16 C6 Cl4 117.5(5) . .
C16 C6 C13 120.7(6) . .
C1 C7 C4 120.1(6) . .
C1 C7 C12 119.4(6) . .
C12 C7 C4 120.5(6) . .
C11 C8 C17 120.2(6) . .
C18 C8 C11 119.7(6) . .
C18 C8 C17 120.1(6) . .
C21 C9 Cl5 117.6(5) . .
C21 C9 C22 120.9(6) . .
C22 C9 Cl5 121.1(5) . .
C3 C10 C15 120.5(6) . .
C20 C10 C3 119.3(6) . .
C20 C10 C15 120.2(6) . .
C8 C11 C11 119.6(4) . 2_654
C12 C11 C8 120.6(6) . .
C12 C11 C11 119.7(4) . 2_654
C3 C12 C7 120.4(6) . .
C11 C12 C3 120.0(6) . .
C11 C12 C7 119.6(6) . .
C4 C13 C21 116.8(6) . .
C6 C13 C4 117.0(6) . .
C6 C13 C21 126.1(6) . .
C2 C14 Cl9 118.2(6) . .
C2 C14 C23 120.0(6) . .
C23 C14 Cl9 121.2(5) . .
C4 C15 C10 119.3(6) . .
C22 C15 C4 120.4(6) . .
C22 C15 C10 120.3(6) . .
C1 C16 Cl3 119.4(5) . .
C6 C16 Cl3 118.9(5) . .
C6 C16 C1 121.4(6) . .
C17 C17 C8 119.4(4) 2_654 .
C23 C17 C8 119.6(6) . .
C23 C17 C17 120.9(4) . 2_654
C2 C18 C1 125.9(6) . .
C8 C18 C1 118.2(6) . .
C8 C18 C2 115.6(6) . .
C19 C19 Cl7 117.6(3) 2_654 .
C19 C19 C23 121.7(4) 2_654 .
C23 C19 Cl7 120.5(5) . .
C10 C20 C20 119.5(4) . 2_654
C10 C20 C24 116.1(6) . .
C24 C20 C20 124.3(4) . 2_654
C9 C21 Cl1 117.9(5) . .
C9 C21 C13 121.6(6) . .
C13 C21 Cl1 119.8(5) . .
C9 C22 C5 126.1(6) . .
C15 C22 C5 117.0(6) . .
C15 C22 C9 116.9(6) . .
C17 C23 C14 116.2(6) . .
C17 C23 C19 117.2(7) . .
C19 C23 C14 125.7(6) . .
C5 C24 Cl6 119.5(5) . .
C5 C24 C20 120.5(6) . .
C20 C24 Cl6 119.6(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C21 1.727(7) .
Cl2 C2 1.722(7) .
Cl3 C16 1.730(6) .
Cl4 C6 1.737(7) .
Cl5 C9 1.726(7) .
Cl6 C24 1.717(7) .
Cl7 C19 1.727(7) .
Cl8 C5 1.727(7) .
Cl9 C14 1.719(7) .
C1 C7 1.403(9) .
C1 C16 1.423(10) .
C1 C18 1.440(9) .
C2 C14 1.365(9) .
C2 C18 1.415(9) .
C3 C3 1.405(13) 2_654
C3 C10 1.429(9) .
C3 C12 1.415(9) .
C4 C7 1.423(9) .
C4 C13 1.417(9) .
C4 C15 1.429(8) .
C5 C22 1.421(10) .
C5 C24 1.368(10) .
C6 C13 1.414(9) .
C6 C16 1.374(9) .
C7 C12 1.421(9) .
C8 C11 1.409(9) .
C8 C17 1.433(9) .
C8 C18 1.403(10) .
C9 C21 1.380(9) .
C9 C22 1.414(10) .
C10 C15 1.431(9) .
C10 C20 1.411(9) .
C11 C11 1.437(13) 2_654
C11 C12 1.405(9) .
C13 C21 1.418(9) .
C14 C23 1.437(10) .
C15 C22 1.411(9) .
C17 C17 1.419(14) 2_654
C17 C23 1.407(9) .
C19 C19 1.372(14) 2_654
C19 C23 1.415(10) .
C20 C20 1.437(13) 2_654
C20 C24 1.436(9) .
