#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180197 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/93/7109315.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_7109315
loop_
_publ_author_name
'Shin-ichiro Kawano'
'Martin Baumgarten'
'Dennis Chercka'
'Volker Enkelmann'
'Klaus Mullen'
_publ_section_title
;
 Electron donors and acceptors based on 2,7-functionalized
 pyrene-4,5,9,10-tetraone
;
_journal_name_full               Chem.Commun.
_journal_page_first              5058
_journal_paper_doi               10.1039/c3cc39141h
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C32 H22 N4 O4'
_chemical_formula_sum            'C32 H22 N4 O4'
_chemical_formula_weight         526.55
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             10-08-10
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 115.853(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2441(5)
_cell_length_b                   14.6744(7)
_cell_length_c                   13.2556(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2493.43(17)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11259
_diffrn_reflns_theta_full        30.021
_diffrn_reflns_theta_max         30.021
_diffrn_reflns_theta_min         3.120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0674
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000329
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
1.91 0.883 1.38
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0632
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0591
_reflns_limit_h_max              18
_reflns_limit_h_min              -20
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2457
_reflns_number_total             3640
_reflns_threshold_expression     I>3.0σ(I)
_cod_data_source_file            c3cc39141h.txt
_cod_data_source_block           4Omepytcnq
_cod_original_cell_volume        2493.44(17)
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               7109315
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.29447(8) 0.37732(7) -0.23365(8) 0.0229 1.0000 Uani . .
O2 O 0.20630(9) 0.31580(8) 0.26077(8) 0.0254 1.0000 Uani . .
C1 C 0.24883(10) 0.29814(9) 0.00651(10) 0.0171 1.0000 Uani . .
C2 C 0.26203(10) 0.35701(9) -0.07121(11) 0.0180 1.0000 Uani . .
C3 C 0.26083(11) 0.45187(10) -0.05714(11) 0.0211 1.0000 Uani . .
C4 C 0.24641(11) 0.48731(10) 0.03274(12) 0.0227 1.0000 Uani . .
C5 C 0.23395(11) 0.43051(10) 0.11000(11) 0.0213 1.0000 Uani . .
C6 C 0.23510(10) 0.33538(9) 0.09823(10) 0.0176 1.0000 Uani . .
C7 C 0.27839(10) 0.31788(10) -0.16201(11) 0.0193 1.0000 Uani . .
C8 C 0.40264(12) 0.38471(12) -0.20975(14) 0.0294 1.0000 Uani . .
C9 C 0.22231(10) 0.27428(10) 0.17661(10) 0.0189 1.0000 Uani . .
C10 C 0.26112(13) 0.28083(12) 0.37266(12) 0.0291 1.0000 Uani . .
C11 C 0.51023(13) 0.36331(11) 0.16354(13) 0.0292 1.0000 Uani . .
C12 C 0.5000 0.31186(15) 0.2500 0.0236 1.0000 Uani S T
C13 C 0.5000 0.21798(14) 0.2500 0.0204 1.0000 Uani S T
C14 C 0.49716(11) 0.16788(11) 0.34220(11) 0.0214 1.0000 Uani . .
C15 C 0.49882(11) 0.07577(10) 0.34302(11) 0.0210 1.0000 Uani . .
C16 C 0.5000 0.02511(14) 0.2500 0.0194 1.0000 Uani S T
C17 C 0.5000 -0.06890(14) 0.2500 0.0204 1.0000 Uani S T
C18 C 0.48483(11) -0.12021(10) 0.15233(12) 0.0222 1.0000 Uani . .
N11 N 0.52141(14) 0.40322(11) 0.09473(13) 0.0402 1.0000 Uani . .
N12 N 0.46740(11) -0.16121(10) 0.07197(11) 0.0305 1.0000 Uani . .
H31 H 0.2701 0.4917 -0.1086 0.0266 1.0000 Uiso R .
H41 H 0.2450 0.5515 0.0413 0.0301 1.0000 Uiso R .
H51 H 0.2243 0.4558 0.1708 0.0271 1.0000 Uiso R .
H81 H 0.4101 0.4263 -0.2607 0.0384 1.0000 Uiso R .
H82 H 0.4414 0.4060 -0.1352 0.0384 1.0000 Uiso R .
H83 H 0.4280 0.3265 -0.2176 0.0384 1.0000 Uiso R .
H101 H 0.2432 0.3154 0.4223 0.0378 1.0000 Uiso R .
H102 H 0.3341 0.2850 0.3955 0.0378 1.0000 Uiso R .
H103 H 0.2424 0.2189 0.3742 0.0378 1.0000 Uiso R .
H141 H 0.4940 0.1999 0.4029 0.0270 1.0000 Uiso R .
H151 H 0.4990 0.0437 0.4053 0.0267 1.0000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . O1 C8 . 112.34(11) yes
C9 . O2 C10 . 118.15(11) yes
C1 4_555 C1 C2 . 119.88(14) yes
C1 4_555 C1 C6 . 120.24(15) yes
C2 . C1 C6 . 119.87(12) yes
C1 . C2 C3 . 119.58(12) yes
C1 . C2 C7 . 119.00(12) yes
C3 . C2 C7 . 121.40(12) yes
C2 . C3 C4 . 119.83(12) yes
C2 . C3 H31 . 120.0 no
C4 . C3 H31 . 120.2 no
C3 . C4 C5 . 121.28(13) yes
C3 . C4 H41 . 119.4 no
C5 . C4 H41 . 119.3 no
C4 . C5 C6 . 120.14(12) yes
C4 . C5 H51 . 120.2 no
C6 . C5 H51 . 119.7 no
C1 . C6 C5 . 119.29(12) yes
C1 . C6 C9 . 118.97(12) yes
C5 . C6 C9 . 121.74(12) yes
C2 . C7 O1 . 117.30(12) yes
C2 . C7 C9 4_555 121.26(12) yes
O1 . C7 C9 4_555 121.43(12) yes
O1 . C8 H81 . 109.5 no
O1 . C8 H82 . 109.6 no
H81 . C8 H82 . 109.5 no
O1 . C8 H83 . 109.3 no
H81 . C8 H83 . 109.5 no
H82 . C8 H83 . 109.5 no
C6 . C9 O2 . 115.26(12) yes
C6 . C9 C7 4_555 120.58(12) yes
O2 . C9 C7 4_555 124.08(12) yes
O2 . C10 H101 . 109.6 no
O2 . C10 H102 . 109.4 no
H101 . C10 H102 . 109.5 no
O2 . C10 H103 . 109.4 no
H101 . C10 H103 . 109.5 no
H102 . C10 H103 . 109.5 no
C12 . C11 N11 . 177.79(18) yes
C11 . C12 C11 5_655 116.4(2) yes
C11 . C12 C13 . 121.82(10) yes
C11 5_655 C12 C13 . 121.82(10) yes
C14 5_655 C13 C12 . 120.66(9) yes
C14 5_655 C13 C14 . 118.68(19) yes
C12 . C13 C14 . 120.66(9) yes
C13 . C14 C15 . 120.65(14) yes
C13 . C14 H141 . 119.7 no
C15 . C14 H141 . 119.7 no
C14 . C15 C16 . 120.92(14) yes
C14 . C15 H151 . 119.7 no
C16 . C15 H151 . 119.3 no
C15 . C16 C15 5_655 118.13(18) yes
C15 . C16 C17 . 120.93(9) yes
C15 5_655 C16 C17 . 120.93(9) yes
C18 5_655 C17 C16 . 121.77(9) yes
C18 5_655 C17 C18 . 116.47(18) yes
C16 . C17 C18 . 121.77(9) yes
C17 . C18 N12 . 176.63(15) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.3801(16) yes
O1 C8 . 1.4354(18) yes
O2 C9 . 1.3746(16) yes
O2 C10 . 1.4363(17) yes
C1 C1 4_555 1.425(3) yes
C1 C2 . 1.4184(18) yes
C1 C6 . 1.4221(17) yes
C2 C3 . 1.4056(19) yes
C2 C7 . 1.4413(18) yes
C3 C4 . 1.395(2) yes
C3 H31 . 0.950 no
C4 C5 . 1.3906(19) yes
C4 H41 . 0.950 no
C5 C6 . 1.405(2) yes
C5 H51 . 0.950 no
C6 C9 . 1.4429(18) yes
C7 C9 4_555 1.366(2) yes
C8 H81 . 0.950 no
C8 H82 . 0.950 no
C8 H83 . 0.950 no
C10 H101 . 0.950 no
C10 H102 . 0.950 no
C10 H103 . 0.950 no
C11 C12 . 1.432(2) yes
C11 N11 . 1.152(2) yes
C12 C13 . 1.378(3) yes
C13 C14 5_655 1.4419(17) yes
C13 C14 . 1.4419(17) yes
C14 C15 . 1.352(2) yes
C14 H141 . 0.950 no
C15 C16 . 1.4462(17) yes
C15 H151 . 0.950 no
C16 C17 . 1.379(3) yes
C17 C18 5_655 1.4304(18) yes
C17 C18 . 1.4304(18) yes
C18 N12 . 1.152(2) yes
