#------------------------------------------------------------------------------
#$Date: 2017-10-18 11:37:19 +0300 (Wed, 18 Oct 2017) $
#$Revision: 202120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/77/1547723.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_1547723
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         378.44
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.488(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.0759(15)
_cell_length_b                   12.6702(5)
_cell_length_c                   7.9552(3)
_cell_measurement_reflns_used    12020
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      3.69
_cell_volume                     3760.9(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21350
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.185
_diffrn_reflns_theta_min         3.684
_diffrn_source                   'Varimax 40 kV 30 mA Rotating anode'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0800P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1475
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2340
_reflns_number_total             3443
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms16089-s2.cif
_cod_data_source_block           20140218
_cod_database_code               1547723
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2013-2
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 0.53728(7) 0.39265(16) 0.1162(3) 0.0613(6) Uani 1 1 d . . . . .
C2 C 0.55770(6) 0.45822(17) 0.2271(3) 0.0614(6) Uani 1 1 d . . . . .
C3 C 0.59452(6) 0.43546(14) 0.2932(3) 0.0560(5) Uani 1 1 d . . . . .
C4 C 0.61615(7) 0.51057(16) 0.3990(3) 0.0604(6) Uani 1 1 d . . . . .
C5 C 0.65216(7) 0.49973(16) 0.4444(3) 0.0600(6) Uani 1 1 d . . . . .
C6 C 0.66843(5) 0.41251(14) 0.3788(3) 0.0544(5) Uani 1 1 d . . . . .
C7 C 0.70563(6) 0.39454(14) 0.3788(3) 0.0544(5) Uani 1 1 d . . . . .
C8 C 0.73347(6) 0.45644(18) 0.4573(3) 0.0622(6) Uani 1 1 d . . . . .
C9 C 0.77040(7) 0.44524(19) 0.4601(3) 0.0672(6) Uani 1 1 d . . . . .
C10 C 0.78711(7) 0.37065(19) 0.3803(3) 0.0676(6) Uani 1 1 d . . . . .
C11 C 0.77268(6) 0.28461(19) 0.2756(3) 0.0649(6) Uani 1 1 d . . . . .
C12 C 0.73755(6) 0.25372(17) 0.2275(3) 0.0594(6) Uani 1 1 d . . . . .
C13 C 0.70684(6) 0.29892(14) 0.2705(3) 0.0534(5) Uani 1 1 d . . . . .
C14 C 0.67193(5) 0.26448(15) 0.2167(3) 0.0520(5) Uani 1 1 d . . . . .
C15 C 0.64764(5) 0.33225(14) 0.2823(3) 0.0512(5) Uani 1 1 d . . . . .
C16 C 0.60932(5) 0.33857(14) 0.2472(3) 0.0521(5) Uani 1 1 d . . . . .
C17 C 0.58521(5) 0.25964(15) 0.1569(3) 0.0515(5) Uani 1 1 d . . . . .
C18 C 0.59248(5) 0.14864(14) 0.1540(2) 0.0501(5) Uani 1 1 d . . . . .
C19 C 0.62049(5) 0.08499(15) 0.2508(3) 0.0519(5) Uani 1 1 d . . . . .
C20 C 0.61337(5) -0.02048(14) 0.2163(3) 0.0495(5) Uani 1 1 d . . . . .
C21 C 0.63365(6) -0.10588(15) 0.2935(3) 0.0557(5) Uani 1 1 d . . . . .
C22 C 0.62827(6) -0.21188(16) 0.2646(3) 0.0593(6) Uani 1 1 d . . . . .
C23 C 0.60078(6) -0.26280(17) 0.1499(3) 0.0597(6) Uani 1 1 d . . . . .
C24 C 0.57162(6) -0.22199(17) 0.0432(3) 0.0605(6) Uani 1 1 d . . . . .
C25 C 0.56146(6) -0.11524(16) 0.0173(3) 0.0554(5) Uani 1 1 d . . . . .
C26 C 0.57891(5) -0.02700(14) 0.0891(3) 0.0515(5) Uani 1 1 d . . . . .
C27 C 0.56692(5) 0.07959(15) 0.0573(3) 0.0517(5) Uani 1 1 d . . . . .
C28 C 0.53410(6) 0.11713(17) -0.0380(3) 0.0596(6) Uani 1 1 d . . . . .
C29 C 0.52584(6) 0.22025(18) -0.0241(3) 0.0611(6) Uani 1 1 d . . . . .
C30 C 0.54963(6) 0.29113(16) 0.0800(3) 0.0570(5) Uani 1 1 d . . . . .
H1 H 0.5117(5) 0.4059(14) 0.064(2) 0.062(6) Uiso 1 1 d . . . . .
H2 H 0.5492(5) 0.5277(17) 0.263(2) 0.070(6) Uiso 1 1 d . . . . .
H3 H 0.6029(5) 0.5769(16) 0.433(3) 0.074(6) Uiso 1 1 d . . . . .
H4 H 0.6661(5) 0.5532(15) 0.518(3) 0.062(6) Uiso 1 1 d . . . . .
H5 H 0.7260(5) 0.5184(16) 0.527(3) 0.068(6) Uiso 1 1 d . . . . .
H6 H 0.7864(5) 0.4971(15) 0.528(3) 0.067(6) Uiso 1 1 d . . . . .
H7 H 0.8130(6) 0.3752(16) 0.402(3) 0.077(7) Uiso 1 1 d . . . . .
H8 H 0.7892(6) 0.2378(17) 0.232(3) 0.080(7) Uiso 1 1 d . . . . .
H9 H 0.7332(4) 0.1881(14) 0.148(2) 0.049(5) Uiso 1 1 d . . . . .
H10 H 0.6661(5) 0.2004(14) 0.143(2) 0.057(5) Uiso 1 1 d . . . . .
H11 H 0.6421(5) 0.1144(14) 0.339(2) 0.054(5) Uiso 1 1 d . . . . .
H12 H 0.6558(5) -0.0841(15) 0.385(3) 0.073(6) Uiso 1 1 d . . . . .
H13 H 0.6464(5) -0.2617(15) 0.336(3) 0.067(6) Uiso 1 1 d . . . . .
H14 H 0.6023(4) -0.3383(15) 0.143(2) 0.053(5) Uiso 1 1 d . . . . .
H15 H 0.5552(5) -0.2683(15) -0.029(2) 0.056(6) Uiso 1 1 d . . . . .
H16 H 0.5385(5) -0.0984(15) -0.064(3) 0.067(6) Uiso 1 1 d . . . . .
H17 H 0.5167(6) 0.0676(16) -0.108(3) 0.073(7) Uiso 1 1 d . . . . .
H18 H 0.5018(5) 0.2492(15) -0.078(3) 0.063(6) 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 0.0181 0.0091 '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'
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
C2 C1 C30 121.5(2) . .
C2 C1 H1 124.2(11) . .
C30 C1 H1 113.8(11) . .
C1 C2 C3 121.1(2) . .
C1 C2 H2 123.7(11) . .
C3 C2 H2 115.1(11) . .
C4 C3 C2 119.66(19) . .
C4 C3 C16 121.1(2) . .
C2 C3 C16 119.23(19) . .
C5 C4 C3 121.8(2) . .
C5 C4 H3 121.9(11) . .
C3 C4 H3 116.1(11) . .
C4 C5 C6 118.4(2) . .
C4 C5 H4 119.3(11) . .
C6 C5 H4 122.3(11) . .
C5 C6 C15 121.42(19) . .
C5 C6 C7 128.92(18) . .
C15 C6 C7 109.32(17) . .
C8 C7 C6 125.8(2) . .
C8 C7 C13 128.3(2) . .
C6 C7 C13 105.84(16) . .
C7 C8 C9 129.1(2) . .
C7 C8 H5 114.3(11) . .
C9 C8 H5 116.6(11) . .
C10 C9 C8 128.2(2) . .
C10 C9 H6 115.1(12) . .
C8 C9 H6 116.7(12) . .
C9 C10 C11 130.2(2) . .
C9 C10 H7 115.5(13) . .
C11 C10 H7 114.3(13) . .
C12 C11 C10 128.8(2) . .
C12 C11 H8 112.8(13) . .
C10 C11 H8 118.4(13) . .
C11 C12 C13 128.9(2) . .
C11 C12 H9 115.1(9) . .
C13 C12 H9 115.9(9) . .
C14 C13 C12 126.3(2) . .
C14 C13 C7 107.25(18) . .
C12 C13 C7 126.48(19) . .
C13 C14 C15 110.36(18) . .
C13 C14 H10 121.7(10) . .
C15 C14 H10 127.9(10) . .
C6 C15 C16 120.21(17) . .
C6 C15 C14 107.20(18) . .
C16 C15 C14 131.91(18) . .
C3 C16 C15 115.87(17) . .
C3 C16 C17 118.51(18) . .
C15 C16 C17 125.39(17) . .
C30 C17 C18 115.90(17) . .
C30 C17 C16 118.25(17) . .
C18 C17 C16 125.44(17) . .
C27 C18 C19 107.55(17) . .
C27 C18 C17 120.03(17) . .
C19 C18 C17 131.95(17) . .
C20 C19 C18 110.03(17) . .
C20 C19 H11 125.4(10) . .
C18 C19 H11 124.4(10) . .
C19 C20 C21 126.35(19) . .
C19 C20 C26 107.45(16) . .
C21 C20 C26 126.11(18) . .
C22 C21 C20 129.3(2) . .
C22 C21 H12 116.9(11) . .
C20 C21 H12 113.8(11) . .
C21 C22 C23 128.9(2) . .
C21 C22 H13 116.8(11) . .
C23 C22 H13 114.3(11) . .
C24 C23 C22 130.0(2) . .
C24 C23 H14 113.2(10) . .
C22 C23 H14 116.8(10) . .
C23 C24 C25 128.5(2) . .
C23 C24 H15 119.7(11) . .
C25 C24 H15 111.8(11) . .
C26 C25 C24 128.9(2) . .
C26 C25 H16 112.7(11) . .
C24 C25 H16 118.5(11) . .
C25 C26 C27 125.92(19) . .
C25 C26 C20 128.16(19) . .
C27 C26 C20 105.91(16) . .
C28 C27 C18 121.57(18) . .
C28 C27 C26 129.11(18) . .
C18 C27 C26 109.04(17) . .
C29 C28 C27 118.5(2) . .
C29 C28 H17 120.9(12) . .
C27 C28 H17 120.5(12) . .
C28 C29 C30 121.8(2) . .
C28 C29 H18 121.8(11) . .
C30 C29 H18 116.2(11) . .
C1 C30 C29 119.6(2) . .
C1 C30 C17 119.40(19) . .
C29 C30 C17 120.94(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.341(3) .
C1 C30 1.419(3) .
C1 H1 0.993(19) .
C2 C3 1.426(3) .
C2 H2 1.00(2) .
C3 C4 1.420(3) .
C3 C16 1.429(3) .
C4 C5 1.353(3) .
C4 H3 1.04(2) .
C5 C6 1.416(3) .
C5 H4 0.98(2) .
C6 C15 1.417(2) .
C6 C7 1.435(3) .
C7 C8 1.366(3) .
C7 C13 1.492(3) .
C8 C9 1.409(3) .
C8 H5 1.03(2) .
C9 C10 1.364(3) .
C9 H6 0.98(2) .
C10 C11 1.415(3) .
C10 H7 0.97(2) .
C11 C12 1.373(3) .
C11 H8 0.98(2) .
C12 C13 1.404(3) .
C12 H9 1.039(17) .
C13 C14 1.383(3) .
C14 C15 1.434(3) .
C14 H10 1.001(19) .
C15 C16 1.432(3) .
C16 C17 1.448(3) .
C17 C30 1.428(3) .
C17 C18 1.434(2) .
C18 C27 1.416(2) .
C18 C19 1.433(3) .
C19 C20 1.380(2) .
C19 H11 1.037(18) .
C20 C21 1.398(3) .
C20 C26 1.491(3) .
C21 C22 1.371(3) .
C21 H12 1.03(2) .
C22 C23 1.401(3) .
C22 H13 1.02(2) .
C23 C24 1.358(3) .
C23 H14 0.960(18) .
C24 C25 1.411(3) .
C24 H15 0.961(19) .
C25 C26 1.366(3) .
C25 H16 1.00(2) .
C26 C27 1.432(2) .
C27 C28 1.409(3) .
C28 C29 1.353(3) .
C28 H17 1.00(2) .
C29 C30 1.419(3) .
C29 H18 1.000(19) .
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 9.7(3) . . . .
C1 C2 C3 C4 174.8(2) . . . .
C1 C2 C3 C16 -3.2(3) . . . .
C2 C3 C4 C5 -170.2(2) . . . .
C16 C3 C4 C5 7.7(3) . . . .
C3 C4 C5 C6 2.1(3) . . . .
C4 C5 C6 C15 -6.3(3) . . . .
C4 C5 C6 C7 166.4(2) . . . .
C5 C6 C7 C8 6.0(3) . . . .
C15 C6 C7 C8 179.34(19) . . . .
C5 C6 C7 C13 -171.6(2) . . . .
C15 C6 C7 C13 1.7(2) . . . .
C6 C7 C8 C9 -178.6(2) . . . .
C13 C7 C8 C9 -1.5(4) . . . .
C7 C8 C9 C10 1.9(4) . . . .
C8 C9 C10 C11 -0.6(4) . . . .
C9 C10 C11 C12 -0.3(4) . . . .
C10 C11 C12 C13 -0.5(4) . . . .
C11 C12 C13 C14 179.5(2) . . . .
C11 C12 C13 C7 1.2(3) . . . .
C8 C7 C13 C14 -178.79(19) . . . .
C6 C7 C13 C14 -1.3(2) . . . .
C8 C7 C13 C12 -0.2(3) . . . .
C6 C7 C13 C12 177.27(19) . . . .
C12 C13 C14 C15 -178.20(18) . . . .
C7 C13 C14 C15 0.3(2) . . . .
C5 C6 C15 C16 0.7(3) . . . .
C7 C6 C15 C16 -173.21(16) . . . .
C5 C6 C15 C14 172.38(18) . . . .
C7 C6 C15 C14 -1.6(2) . . . .
C13 C14 C15 C6 0.7(2) . . . .
C13 C14 C15 C16 171.02(19) . . . .
C4 C3 C16 C15 -12.7(3) . . . .
C2 C3 C16 C15 165.23(18) . . . .
C4 C3 C16 C17 172.52(17) . . . .
C2 C3 C16 C17 -9.5(3) . . . .
C6 C15 C16 C3 8.5(3) . . . .
C14 C15 C16 C3 -160.7(2) . . . .
C6 C15 C16 C17 -177.13(18) . . . .
C14 C15 C16 C17 13.6(3) . . . .
C3 C16 C17 C30 15.7(3) . . . .
C15 C16 C17 C30 -158.47(19) . . . .
C3 C16 C17 C18 -156.60(19) . . . .
C15 C16 C17 C18 29.2(3) . . . .
C30 C17 C18 C27 9.0(3) . . . .
C16 C17 C18 C27 -178.53(18) . . . .
C30 C17 C18 C19 -162.1(2) . . . .
C16 C17 C18 C19 10.4(3) . . . .
C27 C18 C19 C20 0.5(2) . . . .
C17 C18 C19 C20 172.4(2) . . . .
C18 C19 C20 C21 -176.38(19) . . . .
C18 C19 C20 C26 0.4(2) . . . .
C19 C20 C21 C22 -179.5(2) . . . .
C26 C20 C21 C22 4.3(3) . . . .
C20 C21 C22 C23 -0.3(4) . . . .
C21 C22 C23 C24 -3.2(4) . . . .
C22 C23 C24 C25 1.2(4) . . . .
C23 C24 C25 C26 2.1(4) . . . .
C24 C25 C26 C27 -179.8(2) . . . .
C24 C25 C26 C20 -0.8(3) . . . .
C19 C20 C26 C25 179.78(19) . . . .
C21 C20 C26 C25 -3.5(3) . . . .
C19 C20 C26 C27 -1.1(2) . . . .
C21 C20 C26 C27 175.64(18) . . . .
C19 C18 C27 C28 173.16(19) . . . .
C17 C18 C27 C28 0.1(3) . . . .
C19 C18 C27 C26 -1.3(2) . . . .
C17 C18 C27 C26 -174.32(17) . . . .
C25 C26 C27 C28 6.7(3) . . . .
C20 C26 C27 C28 -172.4(2) . . . .
C25 C26 C27 C18 -179.41(19) . . . .
C20 C26 C27 C18 1.5(2) . . . .
C18 C27 C28 C29 -5.6(3) . . . .
C26 C27 C28 C29 167.6(2) . . . .
C27 C28 C29 C30 1.5(3) . . . .
C2 C1 C30 C29 173.5(2) . . . .
C2 C1 C30 C17 -3.0(3) . . . .
C28 C29 C30 C1 -168.2(2) . . . .
C28 C29 C30 C17 8.2(3) . . . .
C18 C17 C30 C1 163.29(18) . . . .
C16 C17 C30 C1 -9.8(3) . . . .
C18 C17 C30 C29 -13.1(3) . . . .
C16 C17 C30 C29 173.83(18) . . . .
