#------------------------------------------------------------------------------
#$Date: 2017-10-18 11:37:31 +0300 (Wed, 18 Oct 2017) $
#$Revision: 202121 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/77/1547724.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_1547724
loop_
_publ_author_name
'Akitoshi Shiotari'
'Takahiro Nakae'
'Kota Iwata'
'Shigeki Mori'
'Tetsuo Okujima'
'Hidemitsu Uno'
'Hiroshi Sakaguchi'
'Yoshiaki Sugimoto'
_publ_section_title
;
 Strain-induced skeletal rearrangement of a polycyclic aromatic
 hydrocarbon on a copper surface
;
_journal_name_full               'Nature Communications'
_journal_page_first              16089
_journal_paper_doi               10.1038/ncomms16089
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C30 H18'
_chemical_formula_sum            'C30 H18'
_chemical_formula_weight         378.47
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.123(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   37.630(13)
_cell_length_b                   6.3613(19)
_cell_length_c                   16.724(6)
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.25
_cell_measurement_theta_min      2.21
_cell_volume                     3734(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34350
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.357
_diffrn_reflns_theta_min         2.800
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1584.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     343
_refine_ls_number_reflns         14607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1352P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2263
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3849
_reflns_number_total             5744
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ncomms16089-s3.cif
_cod_data_source_block           Nakae
_cod_database_code               1547724
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.64120(5) -0.2106(3) 0.43809(11) 0.0282(4) Uani 1 1 d . . . . .
C2 C 0.63587(6) -0.3986(3) 0.39058(11) 0.0320(4) Uani 1 1 d . . . . .
C3 C 0.60392(6) -0.5218(3) 0.35665(11) 0.0312(4) Uani 1 1 d . . . . .
C4 C 0.56688(6) -0.4889(3) 0.35643(11) 0.0299(4) Uani 1 1 d . . . . .
C5 C 0.55396(5) -0.3225(3) 0.39223(10) 0.0267(4) Uani 1 1 d . . . . .
C6 C 0.57454(5) -0.1509(2) 0.43963(10) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.55783(5) 0.0046(3) 0.47299(10) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.58636(5) 0.1499(2) 0.51760(10) 0.0222(3) Uani 1 1 d . . . . .
C9 C 0.58223(4) 0.3360(2) 0.56079(9) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.54920(5) 0.4162(3) 0.57051(10) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.55846(4) 0.6021(3) 0.61683(10) 0.0229(3) Uani 1 1 d . . . . .
C12 C 0.53222(5) 0.7212(3) 0.63965(10) 0.0247(3) Uani 1 1 d . . . . .
C13 C 0.53751(5) 0.9077(3) 0.68532(11) 0.0264(4) Uani 1 1 d . . . . .
C14 C 0.57075(5) 1.0271(3) 0.71904(10) 0.0259(3) Uani 1 1 d . . . . .
C15 C 0.60627(5) 0.9882(3) 0.71558(10) 0.0257(3) Uani 1 1 d . . . . .
C16 C 0.61944(5) 0.8186(3) 0.67924(10) 0.0237(3) Uani 1 1 d . . . . .
C17 C 0.59991(4) 0.6430(2) 0.63646(9) 0.0206(3) Uani 1 1 d . . . . .
C18 C 0.61386(4) 0.4711(2) 0.60071(9) 0.0212(3) Uani 1 1 d . . . . .
C19 C 0.65114(4) 0.4137(2) 0.59970(9) 0.0216(3) Uani 1 1 d . . . . .
C20 C 0.68328(5) 0.5397(3) 0.63671(11) 0.0276(4) Uani 1 1 d . . . . .
C21 C 0.71971(5) 0.4850(3) 0.63808(11) 0.0270(4) Uani 1 1 d . . . . .
C22 C 0.75181(5) 0.6195(3) 0.67486(13) 0.0341(4) Uani 1 1 d . . . . .
C23 C 0.78708(5) 0.5598(3) 0.67693(13) 0.0360(4) Uani 1 1 d . . . . .
C24 C 0.79187(5) 0.3628(3) 0.64237(12) 0.0353(4) Uani 1 1 d . . . . .
C25 C 0.76179(5) 0.2296(3) 0.60763(11) 0.0337(4) Uani 1 1 d . . . . .
C26 C 0.72459(5) 0.2879(3) 0.60364(10) 0.0268(4) Uani 1 1 d . . . . .
C27 C 0.69230(5) 0.1593(3) 0.56585(10) 0.0263(4) Uani 1 1 d . . . . .
C28 C 0.65585(4) 0.2168(2) 0.55962(9) 0.0223(3) Uani 1 1 d . . . . .
C29 C 0.62216(4) 0.0901(2) 0.51496(9) 0.0212(3) Uani 1 1 d . . . . .
C30 C 0.61568(5) -0.0994(3) 0.46397(10) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.6677(6) -0.156(3) 0.4544(13) 0.028(5) Uiso 1 1 d . . . . .
H2 H 0.6596(6) -0.448(4) 0.3772(14) 0.041(6) Uiso 1 1 d . . . . .
H3 H 0.6065(7) -0.657(4) 0.3285(15) 0.045(6) Uiso 1 1 d . . . . .
H4 H 0.5483(6) -0.600(3) 0.3258(14) 0.038(6) Uiso 1 1 d . . . . .
H5 H 0.5250(6) -0.324(3) 0.3833(13) 0.035(6) Uiso 1 1 d . . . . .
H7 H 0.5283(6) 0.014(3) 0.4676(15) 0.039(6) Uiso 1 1 d . . . . .
H10 H 0.5230(6) 0.346(3) 0.5458(13) 0.035(5) Uiso 1 1 d . . . . .
H12 H 0.5045(6) 0.653(3) 0.6194(13) 0.029(5) Uiso 1 1 d . . . . .
H13 H 0.5135(6) 0.967(3) 0.6936(13) 0.036(6) Uiso 1 1 d . . . . .
H14 H 0.5690(6) 1.162(3) 0.7499(14) 0.036(6) Uiso 1 1 d . . . . .
H15 H 0.6270(6) 1.104(3) 0.7437(13) 0.028(5) Uiso 1 1 d . . . . .
H16 H 0.6470(6) 0.832(3) 0.6822(12) 0.026(5) Uiso 1 1 d . . . . .
H20 H 0.6830(7) 0.691(4) 0.6640(16) 0.052(7) Uiso 1 1 d . . . . .
H22 H 0.7474(6) 0.759(4) 0.6951(15) 0.048(7) Uiso 1 1 d . . . . .
H23 H 0.8089(7) 0.662(4) 0.7022(15) 0.043(6) Uiso 1 1 d . . . . .
H24 H 0.8190(6) 0.322(3) 0.6446(13) 0.035(5) Uiso 1 1 d . . . . .
H25 H 0.7658(6) 0.086(4) 0.5844(15) 0.044(6) Uiso 1 1 d . . . . .
H27 H 0.6970(6) 0.011(3) 0.5472(13) 0.029(5) 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 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
C30 C1 C2 129.59(18) . .
C30 C1 H1 118.5(11) . .
C2 C1 H1 111.9(11) . .
C3 C2 C1 129.92(17) . .
C3 C2 H2 115.5(12) . .
C1 C2 H2 114.6(13) . .
C2 C3 C4 129.34(17) . .
C2 C3 H3 117.7(14) . .
C4 C3 H3 112.9(14) . .
C5 C4 C3 127.77(17) . .
C5 C4 H4 118.3(12) . .
C3 C4 H4 113.9(12) . .
C4 C5 C6 128.92(17) . .
C4 C5 H5 116.1(11) . .
C6 C5 H5 115.0(11) . .
C7 C6 C5 122.75(16) . .
C7 C6 C30 108.02(14) . .
C5 C6 C30 129.23(15) . .
C6 C7 C8 108.07(15) . .
C6 C7 H7 127.2(11) . .
C8 C7 H7 124.7(11) . .
C7 C8 C29 111.03(14) . .
C7 C8 C9 127.73(15) . .
C29 C8 C9 121.24(15) . .
C10 C9 C18 110.59(14) . .
C10 C9 C8 128.51(15) . .
C18 C9 C8 120.89(14) . .
C11 C10 C9 108.59(15) . .
C11 C10 H10 127.6(11) . .
C9 C10 H10 123.8(11) . .
C10 C11 C12 123.55(15) . .
C10 C11 C17 107.63(14) . .
C12 C11 C17 128.82(15) . .
C13 C12 C11 129.56(16) . .
C13 C12 H12 116.9(11) . .
C11 C12 H12 113.6(11) . .
C12 C13 C14 128.18(15) . .
C12 C13 H13 115.4(12) . .
C14 C13 H13 116.4(12) . .
C15 C14 C13 128.67(16) . .
C15 C14 H14 114.5(12) . .
C13 C14 H14 116.9(12) . .
C14 C15 C16 130.54(15) . .
C14 C15 H15 115.3(11) . .
C16 C15 H15 114.2(11) . .
C17 C16 C15 129.40(15) . .
C17 C16 H16 115.6(11) . .
C15 C16 H16 114.9(11) . .
C16 C17 C18 128.65(14) . .
C16 C17 C11 124.76(14) . .
C18 C17 C11 106.57(13) . .
C9 C18 C17 106.61(13) . .
C9 C18 C19 119.33(14) . .
C17 C18 C19 134.04(14) . .
C20 C19 C18 122.41(14) . .
C20 C19 C28 117.81(14) . .
C18 C19 C28 119.78(14) . .
C19 C20 C21 123.30(16) . .
C19 C20 H20 124.6(13) . .
C21 C20 H20 112.1(13) . .
C20 C21 C26 118.68(15) . .
C20 C21 C22 121.84(16) . .
C26 C21 C22 119.47(16) . .
C23 C22 C21 120.46(18) . .
C23 C22 H22 121.5(13) . .
C21 C22 H22 117.9(13) . .
C22 C23 C24 119.97(18) . .
C22 C23 H23 117.7(13) . .
C24 C23 H23 122.3(13) . .
C25 C24 C23 120.93(17) . .
C25 C24 H24 120.7(12) . .
C23 C24 H24 118.3(12) . .
C24 C25 C26 120.54(18) . .
C24 C25 H25 120.1(13) . .
C26 C25 H25 119.3(13) . .
C27 C26 C21 118.53(15) . .
C27 C26 C25 122.85(16) . .
C21 C26 C25 118.61(16) . .
C28 C27 C26 123.33(15) . .
C28 C27 H27 119.5(11) . .
C26 C27 H27 117.0(11) . .
C27 C28 C29 123.08(14) . .
C27 C28 C19 118.15(14) . .
C29 C28 C19 118.78(14) . .
C8 C29 C30 106.42(14) . .
C8 C29 C28 119.73(14) . .
C30 C29 C28 133.85(14) . .
C1 C30 C29 128.55(16) . .
C1 C30 C6 124.97(16) . .
C29 C30 C6 106.42(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C30 1.382(2) .
C1 C2 1.410(2) .
C1 H1 1.00(2) .
C2 C3 1.375(3) .
C2 H2 1.04(2) .
C3 C4 1.408(3) .
C3 H3 1.00(2) .
C4 C5 1.387(2) .
C4 H4 0.99(2) .
C5 C6 1.406(2) .
C5 H5 1.04(2) .
C6 C7 1.392(2) .
C6 C30 1.489(2) .
C7 C8 1.410(2) .
C7 H7 1.09(2) .
C8 C29 1.416(2) .
C8 C9 1.424(2) .
C9 C10 1.406(2) .
C9 C18 1.424(2) .
C10 C11 1.388(2) .
C10 H10 1.02(2) .
C11 C12 1.402(2) .
C11 C17 1.497(2) .
C12 C13 1.386(2) .
C12 H12 1.06(2) .
C13 C14 1.397(2) .
C13 H13 1.04(2) .
C14 C15 1.381(2) .
C14 H14 1.02(2) .
C15 C16 1.412(2) .
C15 H15 1.05(2) .
C16 C17 1.386(2) .
C16 H16 1.03(2) .
C17 C18 1.434(2) .
C18 C19 1.455(2) .
C19 C20 1.396(2) .
C19 C28 1.462(2) .
C20 C21 1.406(2) .
C20 H20 1.07(2) .
C21 C26 1.419(2) .
C21 C22 1.426(3) .
C22 C23 1.369(3) .
C22 H22 0.99(2) .
C23 C24 1.418(3) .
C23 H23 1.01(2) .
C24 C25 1.365(3) .
C24 H24 1.04(2) .
C25 C26 1.426(2) .
C25 H25 1.02(2) .
C26 C27 1.411(2) .
C27 C28 1.387(2) .
C27 H27 1.026(19) .
C28 C29 1.460(2) .
C29 C30 1.445(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C30 C1 C2 C3 0.5(3) . . . .
C1 C2 C3 C4 3.4(3) . . . .
C2 C3 C4 C5 -1.0(3) . . . .
C3 C4 C5 C6 -2.4(3) . . . .
C4 C5 C6 C7 -179.09(16) . . . .
C4 C5 C6 C30 0.5(3) . . . .
C5 C6 C7 C8 179.16(15) . . . .
C30 C6 C7 C8 -0.51(17) . . . .
C6 C7 C8 C29 -0.76(18) . . . .
C6 C7 C8 C9 178.91(15) . . . .
C7 C8 C9 C10 1.3(3) . . . .
C29 C8 C9 C10 -179.03(14) . . . .
C7 C8 C9 C18 -177.87(14) . . . .
C29 C8 C9 C18 1.8(2) . . . .
C18 C9 C10 C11 -0.36(18) . . . .
C8 C9 C10 C11 -179.63(15) . . . .
C9 C10 C11 C12 -178.61(14) . . . .
C9 C10 C11 C17 0.82(18) . . . .
C10 C11 C12 C13 179.96(17) . . . .
C17 C11 C12 C13 0.7(3) . . . .
C11 C12 C13 C14 1.4(3) . . . .
C12 C13 C14 C15 -0.4(3) . . . .
C13 C14 C15 C16 -1.2(3) . . . .
C14 C15 C16 C17 0.1(3) . . . .
C15 C16 C17 C18 -179.29(16) . . . .
C15 C16 C17 C11 2.6(3) . . . .
C10 C11 C17 C16 177.52(14) . . . .
C12 C11 C17 C16 -3.1(3) . . . .
C10 C11 C17 C18 -0.98(17) . . . .
C12 C11 C17 C18 178.41(15) . . . .
C10 C9 C18 C17 -0.27(17) . . . .
C8 C9 C18 C17 179.06(14) . . . .
C10 C9 C18 C19 178.57(13) . . . .
C8 C9 C18 C19 -2.1(2) . . . .
C16 C17 C18 C9 -177.68(15) . . . .
C11 C17 C18 C9 0.75(16) . . . .
C16 C17 C18 C19 3.7(3) . . . .
C11 C17 C18 C19 -177.85(16) . . . .
C9 C18 C19 C20 179.27(15) . . . .
C17 C18 C19 C20 -2.3(3) . . . .
C9 C18 C19 C28 -1.4(2) . . . .
C17 C18 C19 C28 177.07(15) . . . .
C18 C19 C20 C21 178.56(15) . . . .
C28 C19 C20 C21 -0.8(2) . . . .
C19 C20 C21 C26 -2.9(3) . . . .
C19 C20 C21 C22 178.64(16) . . . .
C20 C21 C22 C23 178.54(18) . . . .
C26 C21 C22 C23 0.1(3) . . . .
C21 C22 C23 C24 0.0(3) . . . .
C22 C23 C24 C25 -0.7(3) . . . .
C23 C24 C25 C26 1.4(3) . . . .
C20 C21 C26 C27 2.9(2) . . . .
C22 C21 C26 C27 -178.60(16) . . . .
C20 C21 C26 C25 -177.96(16) . . . .
C22 C21 C26 C25 0.5(2) . . . .
C24 C25 C26 C27 177.81(17) . . . .
C24 C25 C26 C21 -1.3(3) . . . .
C21 C26 C27 C28 0.8(3) . . . .
C25 C26 C27 C28 -178.25(16) . . . .
C26 C27 C28 C29 175.40(15) . . . .
C26 C27 C28 C19 -4.5(2) . . . .
C20 C19 C28 C27 4.4(2) . . . .
C18 C19 C28 C27 -174.95(14) . . . .
C20 C19 C28 C29 -175.52(14) . . . .
C18 C19 C28 C29 5.1(2) . . . .
C7 C8 C29 C30 1.73(17) . . . .
C9 C8 C29 C30 -177.97(14) . . . .
C7 C8 C29 C28 -178.22(13) . . . .
C9 C8 C29 C28 2.1(2) . . . .
C27 C28 C29 C8 174.60(14) . . . .
C19 C28 C29 C8 -5.5(2) . . . .
C27 C28 C29 C30 -5.3(3) . . . .
C19 C28 C29 C30 174.61(15) . . . .
C2 C1 C30 C29 177.93(17) . . . .
C2 C1 C30 C6 -5.2(3) . . . .
C8 C29 C30 C1 175.37(16) . . . .
C28 C29 C30 C1 -4.7(3) . . . .
C8 C29 C30 C6 -1.95(16) . . . .
C28 C29 C30 C6 177.98(16) . . . .
C7 C6 C30 C1 -175.90(15) . . . .
C5 C6 C30 C1 4.5(3) . . . .
C7 C6 C30 C29 1.54(17) . . . .
C5 C6 C30 C29 -178.09(15) . . . .
