#------------------------------------------------------------------------------
#$Date: 2019-08-27 12:02:30 +0300 (Tue, 27 Aug 2019) $
#$Revision: 217760 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/34/7233497.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_7233497
loop_
_publ_author_name
'Chenguang Wang'
'Dong Chen'
'Weiping Chen'
'Shanyong Chen'
'Kaiqi Ye'
'Hongyu Zhang'
'Jingying Zhang'
'Yue Wang'
_publ_section_title
;
 Polymorph, assembly, luminescence and semiconductor properties of a
 quinacridone derivative with extended pi-conjugated framework
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5548
_journal_page_last               5556
_journal_paper_doi               10.1039/C3TC30803K
_journal_volume                  1
_journal_year                    2013
_chemical_formula_sum            'C64 H82 N4 O2'
_chemical_formula_weight         939.34
_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_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.358(17)
_cell_angle_beta                 100.19(2)
_cell_angle_gamma                90.81(2)
_cell_formula_units_Z            1
_cell_length_a                   8.958(6)
_cell_length_b                   10.065(5)
_cell_length_c                   15.398(8)
_cell_measurement_reflns_used    8278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      3.03
_cell_volume                     1342.6(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13284
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0525
_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)+(0.0815P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                3089
_reflns_number_total             6080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_original_cell_volume        1342.6(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233497
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 0.4103(2) 0.40999(18) 0.29514(12) 0.0491(4) Uani 1 1 d . . .
C2 C 0.3567(2) 0.47381(19) 0.22289(14) 0.0601(5) Uani 1 1 d . . .
H2 H 0.2750 0.5297 0.2241 0.072 Uiso 1 1 calc R . .
C3 C 0.4279(3) 0.4515(2) 0.15044(15) 0.0703(6) Uani 1 1 d . . .
H3 H 0.3944 0.4929 0.1016 0.084 Uiso 1 1 calc R . .
C4 C 0.5496(3) 0.3679(2) 0.14885(14) 0.0704(6) Uani 1 1 d . . .
H4 H 0.5956 0.3538 0.0985 0.084 Uiso 1 1 calc R . .
C5 C 0.6041(2) 0.3053(2) 0.21982(12) 0.0588(5) Uani 1 1 d . . .
H5 H 0.6860 0.2499 0.2173 0.071 Uiso 1 1 calc R . .
C6 C 0.5355(2) 0.32548(17) 0.29577(12) 0.0470(4) Uani 1 1 d . . .
C7 C 0.55557(19) 0.27817(16) 0.38140(11) 0.0429(4) Uani 1 1 d . . .
C8 C 0.65963(19) 0.19434(16) 0.42616(11) 0.0423(4) Uani 1 1 d . . .
C9 C 0.63394(19) 0.16593(16) 0.50944(11) 0.0440(4) Uani 1 1 d . . .
C10 C 0.5130(2) 0.22413(19) 0.54834(12) 0.0501(4) Uani 1 1 d . . .
H10 H 0.4974 0.2045 0.6029 0.060 Uiso 1 1 calc R . .
C11 C 0.4187(2) 0.30866(18) 0.50714(12) 0.0518(5) Uani 1 1 d . . .
H11 H 0.3412 0.3483 0.5342 0.062 Uiso 1 1 calc R . .
C12 C 0.4397(2) 0.33475(17) 0.42482(12) 0.0466(4) Uani 1 1 d . . .
C13 C 0.7919(2) 0.14302(17) 0.39097(12) 0.0469(4) Uani 1 1 d . . .
C14 C 0.8981(2) 0.07078(16) 0.44891(11) 0.0434(4) Uani 1 1 d . . .
C15 C 0.86319(19) 0.04118(17) 0.52916(11) 0.0441(4) Uani 1 1 d . . .
C16 C 1.0318(2) 0.03027(17) 0.42087(12) 0.0476(4) Uani 1 1 d . . .
H16 H 1.0522 0.0511 0.3676 0.057 Uiso 1 1 calc R . .
C17 C 0.2284(2) 0.49570(18) 0.39713(13) 0.0538(5) Uani 1 1 d . . .
H17A H 0.2259 0.5753 0.3696 0.065 Uiso 1 1 calc R . .
H17B H 0.2469 0.5262 0.4617 0.065 Uiso 1 1 calc R . .
C18 C 0.0750(2) 0.42093(19) 0.36879(14) 0.0567(5) Uani 1 1 d . . .
H18A H 0.0662 0.3577 0.4085 0.068 Uiso 1 1 calc R . .
H18B H 0.0673 0.3694 0.3084 0.068 Uiso 1 1 calc R . .
C19 C -0.0552(2) 0.5165(2) 0.37099(14) 0.0597(5) Uani 1 1 d . . .
H19A H -0.1478 0.4653 0.3710 0.072 Uiso 1 1 calc R . .
H19B H -0.0341 0.5829 0.4262 0.072 Uiso 1 1 calc R . .
C20 C -0.0795(2) 0.5892(2) 0.29169(16) 0.0701(6) Uani 1 1 d . . .
H20A H 0.0129 0.6418 0.2933 0.084 Uiso 1 1 calc R . .
H20B H -0.0954 0.5218 0.2369 0.084 Uiso 1 1 calc R . .
C21 C -0.2106(2) 0.6824(2) 0.28707(15) 0.0676(6) Uani 1 1 d . . .
H21A H -0.1936 0.7533 0.3400 0.081 Uiso 1 1 calc R . .
H21B H -0.3036 0.6317 0.2869 0.081 Uiso 1 1 calc R . .
C22 C -0.2291(3) 0.7464(3) 0.20307(17) 0.0833(7) Uani 1 1 d . . .
H22A H -0.1373 0.8004 0.2057 0.100 Uiso 1 1 calc R . .
H22B H -0.2380 0.6745 0.1510 0.100 Uiso 1 1 calc R . .
C23 C -0.3607(3) 0.8330(3) 0.18954(18) 0.0881(8) Uani 1 1 d . . .
H23A H -0.3533 0.9047 0.2416 0.106 Uiso 1 1 calc R . .
H23B H -0.4533 0.7791 0.1851 0.106 Uiso 1 1 calc R . .
C24 C -0.3707(4) 0.8954(3) 0.10617(19) 0.1146(11) Uani 1 1 d . . .
H24A H -0.2797 0.9494 0.1102 0.172 Uiso 1 1 calc R . .
H24B H -0.4566 0.9514 0.1015 0.172 Uiso 1 1 calc R . .
H24C H -0.3823 0.8250 0.0540 0.172 Uiso 1 1 calc R . .
C25 C 0.6840(2) 0.02919(17) 0.63122(11) 0.0485(4) Uani 1 1 d . . .
H25A H 0.7190 -0.0618 0.6298 0.058 Uiso 1 1 calc R . .
H25B H 0.5740 0.0235 0.6226 0.058 Uiso 1 1 calc R . .
C26 C 0.7452(2) 0.11306(18) 0.72276(12) 0.0559(5) Uani 1 1 d . . .
H26A H 0.6890 0.1946 0.7313 0.067 Uiso 1 1 calc R . .
H26B H 0.8509 0.1396 0.7261 0.067 Uiso 1 1 calc R . .
C27 C 0.7320(3) 0.0337(2) 0.79757(13) 0.0625(5) Uani 1 1 d . . .
H27A H 0.7360 0.0970 0.8535 0.075 Uiso 1 1 calc R . .
H27B H 0.6339 -0.0151 0.7836 0.075 Uiso 1 1 calc R . .
C28 C 0.8558(3) -0.0662(2) 0.81044(13) 0.0683(6) Uani 1 1 d . . .
H28A H 0.8423 -0.1374 0.7577 0.082 Uiso 1 1 calc R . .
H28B H 0.9536 -0.0201 0.8155 0.082 Uiso 1 1 calc R . .
C29 C 0.8568(3) -0.1292(2) 0.89217(14) 0.0708(6) Uani 1 1 d . . .
H29A H 0.7638 -0.1843 0.8838 0.085 Uiso 1 1 calc R . .
H29B H 0.8576 -0.0578 0.9438 0.085 Uiso 1 1 calc R . .
C30 C 0.9916(3) -0.2164(2) 0.91192(14) 0.0773(7) Uani 1 1 d . . .
H30A H 0.9878 -0.2908 0.8617 0.093 Uiso 1 1 calc R . .
H30B H 1.0847 -0.1627 0.9173 0.093 Uiso 1 1 calc R . .
C31 C 0.9954(3) -0.2721(2) 0.99573(16) 0.0829(7) Uani 1 1 d . . .
H31A H 0.9042 -0.3287 0.9895 0.100 Uiso 1 1 calc R . .
H31B H 0.9953 -0.1979 1.0456 0.100 Uiso 1 1 calc R . .
C32 C 1.1326(3) -0.3543(3) 1.01703(19) 0.0990(9) Uani 1 1 d . . .
H32A H 1.1306 -0.4307 0.9694 0.148 Uiso 1 1 calc R . .
H32B H 1.1309 -0.3852 1.0723 0.148 Uiso 1 1 calc R . .
H32C H 1.2234 -0.2991 1.0229 0.148 Uiso 1 1 calc R . .
N1 N 0.35414(17) 0.41566(15) 0.37324(10) 0.0516(4) Uani 1 1 d . . .
N2 N 0.72892(17) 0.08231(14) 0.55593(9) 0.0474(4) Uani 1 1 d . . .
O1 O 0.82028(16) 0.15954(16) 0.31817(9) 0.0714(4) 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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N1 C1 C2 127.76(18) . .
N1 C1 C6 109.85(15) . .
C2 C1 C6 122.38(18) . .
C3 C2 C1 118.01(19) . .
C3 C2 H2 121.0 . .
C1 C2 H2 121.0 . .
C2 C3 C4 120.79(19) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C5 C4 C3 121.7(2) . .
C5 C4 H4 119.1 . .
C3 C4 H4 119.1 . .
C4 C5 C6 119.66(19) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C5 C6 C1 117.43(16) . .
C5 C6 C7 136.59(17) . .
C1 C6 C7 105.96(16) . .
C12 C7 C8 118.42(16) . .
C12 C7 C6 105.75(14) . .
C8 C7 C6 135.83(17) . .
C9 C8 C7 118.07(16) . .
C9 C8 C13 119.56(14) . .
C7 C8 C13 122.32(16) . .
N2 C9 C10 118.43(15) . .
N2 C9 C8 121.20(16) . .
C10 C9 C8 120.36(14) . .
C11 C10 C9 121.09(17) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C10 C11 C12 119.32(17) . .
C10 C11 H11 120.3 . .
C12 C11 H11 120.3 . .
C11 C12 N1 127.08(17) . .
C11 C12 C7 122.62(15) . .
N1 C12 C7 110.30(16) . .
O1 C13 C8 123.75(15) . .
O1 C13 C14 119.82(17) . .
C8 C13 C14 116.41(15) . .
C16 C14 C15 120.89(14) . .
C16 C14 C13 117.98(15) . .
C15 C14 C13 121.11(16) . .
N2 C15 C16 122.44(15) . 2_756
N2 C15 C14 120.02(14) . .
C16 C15 C14 117.55(16) 2_756 .
C14 C16 C15 121.56(16) . 2_756
C14 C16 H16 119.2 . .
C15 C16 H16 119.2 2_756 .
N1 C17 C18 114.15(16) . .
N1 C17 H17A 108.7 . .
C18 C17 H17A 108.7 . .
N1 C17 H17B 108.7 . .
C18 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C17 C18 C19 112.17(16) . .
C17 C18 H18A 109.2 . .
C19 C18 H18A 109.2 . .
C17 C18 H18B 109.2 . .
C19 C18 H18B 109.2 . .
H18A C18 H18B 107.9 . .
C20 C19 C18 112.56(18) . .
C20 C19 H19A 109.1 . .
C18 C19 H19A 109.1 . .
C20 C19 H19B 109.1 . .
C18 C19 H19B 109.1 . .
H19A C19 H19B 107.8 . .
C21 C20 C19 115.87(18) . .
C21 C20 H20A 108.3 . .
C19 C20 H20A 108.3 . .
C21 C20 H20B 108.3 . .
C19 C20 H20B 108.3 . .
H20A C20 H20B 107.4 . .
C20 C21 C22 111.76(19) . .
C20 C21 H21A 109.3 . .
C22 C21 H21A 109.3 . .
C20 C21 H21B 109.3 . .
C22 C21 H21B 109.3 . .
H21A C21 H21B 107.9 . .
C23 C22 C21 115.8(2) . .
C23 C22 H22A 108.3 . .
C21 C22 H22A 108.3 . .
C23 C22 H22B 108.3 . .
C21 C22 H22B 108.3 . .
H22A C22 H22B 107.4 . .
C22 C23 C24 113.2(2) . .
C22 C23 H23A 108.9 . .
C24 C23 H23A 108.9 . .
C22 C23 H23B 108.9 . .
C24 C23 H23B 108.9 . .
H23A C23 H23B 107.7 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
N2 C25 C26 114.34(15) . .
N2 C25 H25A 108.7 . .
C26 C25 H25A 108.7 . .
N2 C25 H25B 108.7 . .
C26 C25 H25B 108.7 . .
H25A C25 H25B 107.6 . .
C25 C26 C27 111.15(16) . .
C25 C26 H26A 109.4 . .
C27 C26 H26A 109.4 . .
C25 C26 H26B 109.4 . .
C27 C26 H26B 109.4 . .
H26A C26 H26B 108.0 . .
C28 C27 C26 113.40(18) . .
C28 C27 H27A 108.9 . .
C26 C27 H27A 108.9 . .
C28 C27 H27B 108.9 . .
C26 C27 H27B 108.9 . .
H27A C27 H27B 107.7 . .
C29 C28 C27 113.42(19) . .
C29 C28 H28A 108.9 . .
C27 C28 H28A 108.9 . .
C29 C28 H28B 108.9 . .
C27 C28 H28B 108.9 . .
H28A C28 H28B 107.7 . .
C28 C29 C30 113.8(2) . .
C28 C29 H29A 108.8 . .
C30 C29 H29A 108.8 . .
C28 C29 H29B 108.8 . .
C30 C29 H29B 108.8 . .
H29A C29 H29B 107.7 . .
C31 C30 C29 113.1(2) . .
C31 C30 H30A 109.0 . .
C29 C30 H30A 109.0 . .
C31 C30 H30B 109.0 . .
C29 C30 H30B 109.0 . .
H30A C30 H30B 107.8 . .
C30 C31 C32 113.0(2) . .
C30 C31 H31A 109.0 . .
C32 C31 H31A 109.0 . .
C30 C31 H31B 109.0 . .
C32 C31 H31B 109.0 . .
H31A C31 H31B 107.8 . .
C31 C32 H32A 109.5 . .
C31 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C31 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C1 N1 C12 108.11(15) . .
C1 N1 C17 125.26(15) . .
C12 N1 C17 126.62(16) . .
C15 N2 C9 120.90(14) . .
C15 N2 C25 118.15(13) . .
C9 N2 C25 120.85(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.376(2) .
C1 C2 1.399(3) .
C1 C6 1.416(3) .
C2 C3 1.367(3) .
C2 H2 0.9300 .
C3 C4 1.387(3) .
C3 H3 0.9300 .
C4 C5 1.377(3) .
C4 H4 0.9300 .
C5 C6 1.400(3) .
C5 H5 0.9300 .
C6 C7 1.463(2) .
C7 C12 1.405(3) .
C7 C8 1.435(2) .
C8 C9 1.419(2) .
C8 C13 1.452(3) .
C9 N2 1.402(2) .
C9 C10 1.413(3) .
C10 C11 1.366(2) .
C10 H10 0.9300 .
C11 C12 1.383(3) .
C11 H11 0.9300 .
C12 N1 1.384(2) .
C13 O1 1.231(2) .
C13 C14 1.477(2) .
C14 C16 1.386(2) .
C14 C15 1.407(2) .
C15 N2 1.384(2) .
C15 C16 1.398(2) 2_756
C16 C15 1.398(2) 2_756
C16 H16 0.9300 .
C17 N1 1.455(2) .
C17 C18 1.512(3) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.523(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.519(3) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.514(3) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.530(3) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.483(3) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.517(3) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 N2 1.474(2) .
C25 C26 1.512(3) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C27 1.535(3) .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
C27 C28 1.519(3) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 C29 1.506(3) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C29 C30 1.523(3) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C30 C31 1.492(3) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C31 C32 1.511(3) .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
