#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:46:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180195 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/91/7109188.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_7109188
loop_
_publ_author_name
'Hai Xia'
'Danqing Liu'
'Xiaomin Xua'
'Qian Miao'
_publ_section_title
;
 Ambipolar organic semiconductors from electron-accepting cyclopenta-fused
 anthracene
;
_journal_name_full               Chem.Commun.
_journal_page_first              4301
_journal_paper_doi               10.1039/c2cc34992b
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31
_chemical_name_systematic
;
2,7-dimethylcyclopenta[hi]aceanthrylene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.507(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2176(15)
_cell_length_b                   10.4839(15)
_cell_length_c                   12.2150(17)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      -15
_cell_volume                     1307.2(3)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9471
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5479
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0581
_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)+(0.0938P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1835
_reflns_number_gt                1355
_reflns_number_total             2374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc34992b.txt
_cod_data_source_block           dimethylDCPA
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7109188
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.1764(3) 0.3144(3) 1.1238(3) 0.0614(9) Uani 1 1 d .
H1A H 0.2054 0.3887 1.1638 0.092 Uiso 1 1 calc R
H1B H 0.1533 0.2488 1.1743 0.092 Uiso 1 1 calc R
H1C H 0.1013 0.3356 1.0774 0.092 Uiso 1 1 calc R
C2 C 0.2840(3) 0.2677(3) 1.0553(2) 0.0438(7) Uani 1 1 d .
C3 C 0.2733(3) 0.1546(3) 0.9827(2) 0.0392(7) Uani 1 1 d .
C4 C 0.1774(3) 0.0674(3) 0.9578(2) 0.0468(8) Uani 1 1 d .
H4A H 0.0955 0.0742 0.9878 0.056 Uiso 1 1 calc R
C5 C 0.2051(3) -0.0344(3) 0.8849(2) 0.0484(8) Uani 1 1 d .
H5A H 0.1399 -0.0943 0.8687 0.058 Uiso 1 1 calc R
C6 C 0.3225(3) -0.0479(3) 0.8381(2) 0.0447(7) Uani 1 1 d .
H6A H 0.3358 -0.1159 0.7910 0.054 Uiso 1 1 calc R
C7 C 0.4255(3) 0.0416(2) 0.86074(19) 0.0360(7) Uani 1 1 d .
C8 C 0.3962(3) 0.1412(2) 0.93366(19) 0.0359(7) Uani 1 1 d .
C9 C 0.6379(3) 0.1422(2) 0.85983(19) 0.0353(7) Uani 1 1 d .
C10 C 0.5538(3) 0.0437(2) 0.82233(19) 0.0364(7) Uani 1 1 d .
C11 C 0.6304(3) -0.0355(3) 0.7499(2) 0.0441(7) Uani 1 1 d .
H11A H 0.5994 -0.1080 0.7134 0.053 Uiso 1 1 calc R
C12 C 0.7531(3) 0.0123(3) 0.7438(2) 0.0442(7) Uani 1 1 d .
C13 C 0.8638(3) -0.0385(3) 0.6805(2) 0.0570(9) Uani 1 1 d .
H13A H 0.8352 -0.1131 0.6405 0.086 Uiso 1 1 calc R
H13B H 0.9357 -0.0605 0.7302 0.086 Uiso 1 1 calc R
H13C H 0.8915 0.0253 0.6302 0.086 Uiso 1 1 calc R
C14 C 0.7621(3) 0.1269(3) 0.81452(19) 0.0385(7) Uani 1 1 d .
C15 C 0.8599(3) 0.2098(3) 0.8433(2) 0.0463(8) Uani 1 1 d .
H15A H 0.9425 0.2012 0.8150 0.056 Uiso 1 1 calc R
C16 C 0.8334(3) 0.3099(3) 0.9178(2) 0.0492(8) Uani 1 1 d .
H16A H 0.9000 0.3671 0.9369 0.059 Uiso 1 1 calc R
C17 C 0.7142(3) 0.3256(3) 0.9624(2) 0.0453(7) Uani 1 1 d .
H17A H 0.7015 0.3920 1.0113 0.054 Uiso 1 1 calc R
C18 C 0.6089(3) 0.2402(3) 0.93415(19) 0.0369(7) Uani 1 1 d .
C19 C 0.4809(3) 0.2382(2) 0.97214(19) 0.0366(7) Uani 1 1 d .
C20 C 0.4069(3) 0.3155(3) 1.0484(2) 0.0438(7) Uani 1 1 d .
H20A H 0.4394 0.3865 1.0863 0.053 Uiso 1 1 calc R
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 0.0000 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
C20 C2 C3 107.6(2)
C20 C2 C1 128.2(3)
C3 C2 C1 124.1(3)
C4 C3 C8 118.6(3)
C4 C3 C2 134.7(3)
C8 C3 C2 106.8(2)
C3 C4 C5 118.7(3)
C6 C5 C4 122.9(3)
C5 C6 C7 120.5(3)
C10 C7 C8 115.0(2)
C10 C7 C6 129.3(2)
C8 C7 C6 115.7(3)
C19 C8 C7 127.1(2)
C19 C8 C3 109.2(2)
C7 C8 C3 123.7(2)
C10 C9 C18 126.9(2)
C10 C9 C14 109.6(2)
C18 C9 C14 123.4(2)
C9 C10 C7 117.8(2)
C9 C10 C11 106.1(2)
C7 C10 C11 136.1(3)
C12 C11 C10 110.1(3)
C11 C12 C14 107.6(2)
C11 C12 C13 128.2(3)
C14 C12 C13 124.2(3)
C15 C14 C9 119.2(3)
C15 C14 C12 134.1(3)
C9 C14 C12 106.6(2)
C14 C15 C16 118.6(3)
C17 C16 C15 122.8(3)
C16 C17 C18 120.2(3)
C19 C18 C9 115.2(2)
C19 C18 C17 129.1(2)
C9 C18 C17 115.7(2)
C8 C19 C18 118.0(2)
C8 C19 C20 106.6(2)
C18 C19 C20 135.4(3)
C2 C20 C19 109.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.494(4)
C2 C20 1.358(4)
C2 C3 1.481(4)
C3 C4 1.366(4)
C3 C8 1.422(4)
C4 C5 1.426(4)
C5 C6 1.358(4)
C6 C7 1.428(4)
C7 C10 1.412(4)
C7 C8 1.413(4)
C8 C19 1.403(4)
C9 C10 1.408(4)
C9 C18 1.411(4)
C9 C14 1.415(4)
C10 C11 1.465(4)
C11 C12 1.355(4)
C12 C14 1.480(4)
C12 C13 1.496(4)
C14 C15 1.359(4)
C15 C16 1.423(4)
C16 C17 1.365(4)
C17 C18 1.430(4)
C18 C19 1.407(4)
C19 C20 1.469(3)
