#------------------------------------------------------------------------------
#$Date: 2019-07-18 11:32:51 +0300 (Thu, 18 Jul 2019) $
#$Revision: 217152 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233201.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_7233201
loop_
_publ_author_name
'Afshin Dadvand'
'Wei-Hsin Sun'
'Andrey G. Moiseev'
'Francine Belanger-Gariepy'
'Federico Rosei'
'Hong Meng'
'Dmitrii F. Perepichka'
_publ_section_title
;
 1,5-, 2,6- and 9,10-distyrylanthracenes as luminescent organic
 semiconductors
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2817
_journal_page_last               2825
_journal_paper_doi               10.1039/C3TC30247D
_journal_volume                  1
_journal_year                    2013
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C40 H42'
_chemical_formula_sum            'C40 H42'
_chemical_formula_weight         522.74
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.0975(16)
_cell_angle_beta                 99.8398(18)
_cell_angle_gamma                105.7088(16)
_cell_formula_units_Z            1
_cell_length_a                   6.5844(3)
_cell_length_b                   9.2194(3)
_cell_length_c                   13.5405(5)
_cell_measurement_reflns_used    12181
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.50
_cell_measurement_theta_min      3.41
_cell_volume                     758.05(5)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24364
_diffrn_reflns_theta_full        70.81
_diffrn_reflns_theta_max         70.81
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.8227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0532
_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)+(0.1082P)²+0.2318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                2527
_reflns_number_total             2804
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.1347(2) 0.91825(16) 0.45910(10) 0.0263(3) Uani 1 1 d . . .
C2 C 0.0152(2) 0.86273(15) 0.52928(10) 0.0263(3) Uani 1 1 d . . .
C3 C 0.0173(2) 0.72005(16) 0.55706(11) 0.0299(3) Uani 1 1 d . . .
H3 H 0.1084 0.6660 0.5313 0.036 Uiso 1 1 calc R . .
C4 C -0.1078(3) 0.66006(17) 0.61932(11) 0.0333(4) Uani 1 1 d . . .
H4 H -0.1037 0.5650 0.6362 0.040 Uiso 1 1 calc R . .
C5 C -0.2446(3) 0.73941(17) 0.65919(11) 0.0331(4) Uani 1 1 d . . .
H5 H -0.3323 0.6970 0.7024 0.040 Uiso 1 1 calc R . .
C6 C -0.2500(2) 0.87601(16) 0.63547(11) 0.0299(3) Uani 1 1 d . . .
H6 H -0.3417 0.9278 0.6631 0.036 Uiso 1 1 calc R . .
C7 C -0.1220(2) 0.94407(15) 0.57029(10) 0.0261(3) Uani 1 1 d . . .
C8 C 0.2700(2) 0.82923(15) 0.41732(11) 0.0272(3) Uani 1 1 d . . .
H8 H 0.3806 0.8126 0.4648 0.033 Uiso 1 1 calc R . .
C9 C 0.2464(2) 0.77090(15) 0.31728(11) 0.0277(3) Uani 1 1 d . . .
H9 H 0.1399 0.7930 0.2707 0.033 Uiso 1 1 calc R . .
C10 C 0.3688(2) 0.67573(15) 0.27171(11) 0.0276(3) Uani 1 1 d . . .
C11 C 0.2962(2) 0.59731(16) 0.16821(11) 0.0304(3) Uani 1 1 d . . .
H11 H 0.1727 0.6104 0.1275 0.036 Uiso 1 1 calc R . .
C12 C 0.4012(3) 0.50025(16) 0.12340(11) 0.0327(4) Uani 1 1 d . . .
H12 H 0.3462 0.4461 0.0532 0.039 Uiso 1 1 calc R . .
C13 C 0.5856(3) 0.48127(16) 0.17994(12) 0.0320(4) Uani 1 1 d . . .
C14 C 0.6616(2) 0.56274(17) 0.28281(12) 0.0339(4) Uani 1 1 d . . .
H14 H 0.7888 0.5530 0.3225 0.041 Uiso 1 1 calc R . .
C15 C 0.5555(2) 0.65752(17) 0.32828(11) 0.0318(3) Uani 1 1 d . . .
H15 H 0.6101 0.7108 0.3987 0.038 Uiso 1 1 calc R . .
C16 C 0.6971(3) 0.37318(18) 0.13255(13) 0.0384(4) Uani 1 1 d . . .
H16A H 0.8560 0.4226 0.1563 0.046 Uiso 1 1 calc R . .
H16B H 0.6592 0.3581 0.0567 0.046 Uiso 1 1 calc R . .
C17 C 0.6376(3) 0.21464(17) 0.15894(12) 0.0337(4) Uani 1 1 d . . .
H17A H 0.6679 0.2289 0.2348 0.040 Uiso 1 1 calc R . .
H17B H 0.4805 0.1613 0.1312 0.040 Uiso 1 1 calc R . .
C18 C 0.7655(3) 0.11396(17) 0.11429(12) 0.0346(4) Uani 1 1 d . . .
H18A H 0.7257 0.0936 0.0381 0.042 Uiso 1 1 calc R . .
H18B H 0.9221 0.1722 0.1372 0.042 Uiso 1 1 calc R . .
C19 C 0.7266(3) -0.04003(18) 0.14554(13) 0.0400(4) Uani 1 1 d . . .
H19A H 0.7644 -0.0205 0.2217 0.048 Uiso 1 1 calc R . .
H19B H 0.5707 -0.1000 0.1213 0.048 Uiso 1 1 calc R . .
C20 C 0.8587(3) -0.13439(18) 0.10148(13) 0.0441(4) Uani 1 1 d . . .
H20A H 0.8217 -0.1541 0.0261 0.066 Uiso 1 1 calc R . .
H20B H 0.8270 -0.2332 0.1223 0.066 Uiso 1 1 calc R . .
H20C H 1.0134 -0.0771 0.1274 0.066 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 0.0181 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C7 . . 2_576 119.75(12) y
C2 C1 C8 . . . 118.73(12) y
C7 C1 C8 2_576 . . 121.52(12) y
C1 C2 C3 . . . 121.05(12) y
C1 C2 C7 . . . 120.59(12) y
C3 C2 C7 . . . 118.27(13) y
C4 C3 C2 . . . 121.72(13) y
C4 C3 H3 . . . 119.1 ?
C2 C3 H3 . . . 119.1 ?
C3 C4 C5 . . . 120.12(13) y
C3 C4 H4 . . . 119.9 ?
C5 C4 H4 . . . 119.9 ?
C6 C5 C4 . . . 120.06(13) y
C6 C5 H5 . . . 120.0 ?
C4 C5 H5 . . . 120.0 ?
C5 C6 C7 . . . 122.08(13) y
C5 C6 H6 . . . 119.0 ?
C7 C6 H6 . . . 119.0 ?
C1 C7 C6 2_576 . . 122.51(12) y
C1 C7 C2 2_576 . . 119.66(13) y
C6 C7 C2 . . . 117.74(12) y
C9 C8 C1 . . . 124.15(12) y
C9 C8 H8 . . . 117.9 ?
C1 C8 H8 . . . 117.9 ?
C8 C9 C10 . . . 126.54(13) y
C8 C9 H9 . . . 116.7 ?
C10 C9 H9 . . . 116.7 ?
C11 C10 C15 . . . 117.73(13) y
C11 C10 C9 . . . 119.40(13) y
C15 C10 C9 . . . 122.87(13) y
C12 C11 C10 . . . 121.22(14) y
C12 C11 H11 . . . 119.4 ?
C10 C11 H11 . . . 119.4 ?
C11 C12 C13 . . . 120.97(13) y
C11 C12 H12 . . . 119.5 ?
C13 C12 H12 . . . 119.5 ?
C12 C13 C14 . . . 117.83(13) y
C12 C13 C16 . . . 121.23(13) y
C14 C13 C16 . . . 120.92(14) y
C15 C14 C13 . . . 121.42(14) y
C15 C14 H14 . . . 119.3 ?
C13 C14 H14 . . . 119.3 ?
C14 C15 C10 . . . 120.80(13) y
C14 C15 H15 . . . 119.6 ?
C10 C15 H15 . . . 119.6 ?
C13 C16 C17 . . . 113.88(12) y
C13 C16 H16A . . . 108.8 ?
C17 C16 H16A . . . 108.8 ?
C13 C16 H16B . . . 108.8 ?
C17 C16 H16B . . . 108.8 ?
H16A C16 H16B . . . 107.7 ?
C18 C17 C16 . . . 111.48(12) y
C18 C17 H17A . . . 109.3 ?
C16 C17 H17A . . . 109.3 ?
C18 C17 H17B . . . 109.3 ?
C16 C17 H17B . . . 109.3 ?
H17A C17 H17B . . . 108.0 ?
C19 C18 C17 . . . 113.76(13) y
C19 C18 H18A . . . 108.8 ?
C17 C18 H18A . . . 108.8 ?
C19 C18 H18B . . . 108.8 ?
C17 C18 H18B . . . 108.8 ?
H18A C18 H18B . . . 107.7 ?
C20 C19 C18 . . . 112.04(14) y
C20 C19 H19A . . . 109.2 ?
C18 C19 H19A . . . 109.2 ?
C20 C19 H19B . . . 109.2 ?
C18 C19 H19B . . . 109.2 ?
H19A C19 H19B . . . 107.9 ?
C19 C20 H20A . . . 109.5 ?
C19 C20 H20B . . . 109.5 ?
H20A C20 H20B . . . 109.5 ?
C19 C20 H20C . . . 109.5 ?
H20A C20 H20C . . . 109.5 ?
H20B C20 H20C . . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.411(2) y
C1 C7 . 2_576 1.4141(19) y
C1 C8 . . 1.4807(18) y
C2 C3 . . 1.4330(19) y
C2 C7 . . 1.4422(18) y
C3 C4 . . 1.360(2) y
C3 H3 . . 0.9500 ?
C4 C5 . . 1.422(2) y
C4 H4 . . 0.9500 ?
C5 C6 . . 1.361(2) y
C5 H5 . . 0.9500 ?
C6 C7 . . 1.430(2) y
C6 H6 . . 0.9500 ?
C7 C1 . 2_576 1.4141(19) y
C8 C9 . . 1.333(2) y
C8 H8 . . 0.9500 ?
C9 C10 . . 1.4707(18) y
C9 H9 . . 0.9500 ?
C10 C11 . . 1.394(2) y
C10 C15 . . 1.400(2) y
C11 C12 . . 1.3910(19) y
C11 H11 . . 0.9500 ?
C12 C13 . . 1.391(2) y
C12 H12 . . 0.9500 ?
C13 C14 . . 1.395(2) y
C13 C16 . . 1.5088(18) y
C14 C15 . . 1.3855(19) y
C14 H14 . . 0.9500 ?
C15 H15 . . 0.9500 ?
C16 C17 . . 1.529(2) y
C16 H16a . . 0.9900 ?
C16 H16b . . 0.9900 ?
C17 C18 . . 1.5287(19) y
C17 H17a . . 0.9900 ?
C17 H17b . . 0.9900 ?
C18 C19 . . 1.520(2) y
C18 H18a . . 0.9900 ?
C18 H18b . . 0.9900 ?
C19 C20 . . 1.508(2) y
C19 H19a . . 0.9900 ?
C19 H19b . . 0.9900 ?
C20 H20a . . 0.9800 ?
C20 H20b . . 0.9800 ?
C20 H20c . . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C1 C2 C3 2_576 . . . 177.25(12) y
C8 C1 C2 C3 . . . . -2.3(2) y
C7 C1 C2 C7 2_576 . . . 0.8(2) y
C8 C1 C2 C7 . . . . -178.76(11) y
C1 C2 C3 C4 . . . . -175.70(13) y
C7 C2 C3 C4 . . . . 0.8(2) y
C2 C3 C4 C5 . . . . -0.3(2) y
C3 C4 C5 C6 . . . . -0.3(2) y
C4 C5 C6 C7 . . . . 0.4(2) y
C5 C6 C7 C1 . . . 2_576 176.68(13) y
C5 C6 C7 C2 . . . . 0.2(2) y
C1 C2 C7 C1 . . . 2_576 -0.8(2) y
C3 C2 C7 C1 . . . 2_576 -177.35(12) y
C1 C2 C7 C6 . . . . 175.81(12) y
C3 C2 C7 C6 . . . . -0.72(19) y
C2 C1 C8 C9 . . . . 121.22(15) y
C7 C1 C8 C9 2_576 . . . -58.3(2) y
C1 C8 C9 C10 . . . . -176.96(12) y
C8 C9 C10 C11 . . . . 166.90(14) y
C8 C9 C10 C15 . . . . -12.0(2) y
C15 C10 C11 C12 . . . . 2.1(2) y
C9 C10 C11 C12 . . . . -176.90(12) y
C10 C11 C12 C13 . . . . -1.6(2) y
C11 C12 C13 C14 . . . . 0.0(2) y
C11 C12 C13 C16 . . . . 178.49(12) y
C12 C13 C14 C15 . . . . 1.1(2) y
C16 C13 C14 C15 . . . . -177.39(13) y
C13 C14 C15 C10 . . . . -0.6(2) y
C11 C10 C15 C14 . . . . -1.0(2) y
C9 C10 C15 C14 . . . . 177.96(12) y
C12 C13 C16 C17 . . . . -98.74(17) y
C14 C13 C16 C17 . . . . 79.74(18) y
C13 C16 C17 C18 . . . . -176.57(13) y
C16 C17 C18 C19 . . . . 175.23(13) y
C17 C18 C19 C20 . . . . -178.97(12) y
