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#$Date: 2016-03-21 03:41:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178438 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/59/4025999.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_4025999
loop_
_publ_author_name
'Susanne C. Martens'
'Till Riehm'
'Sonja Geib'
'Hubert Wadepohl'
'Lutz H. Gade'
_publ_section_title
;
 Substitutent Effects in the Periphery of 2,9-Bisaryl-tetraazaperopyrene
 Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              609
_journal_page_last               617
_journal_paper_doi               10.1021/jo102141w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C34 H8 F10 N4'
_chemical_formula_weight         662.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_tr14
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.652(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.602(4)
_cell_length_b                   3.7260(13)
_cell_length_c                   28.062(10)
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.58
_cell_measurement_theta_min      2.65
_cell_volume                     1204.9(7)
_computing_cell_refinement
;
SAINT (Bruker AXS, 1997-2008).
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT (Bruker AXS, 1997-2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al., 2004)'
_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23373
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.8141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0517
_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)+(0.0982P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1518
_reflns_number_gt                1774
_reflns_number_total             2754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102141w_si_005.cif
_cod_data_source_block           compound_6a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
F1 F -0.05907(11) 0.6256(4) 0.08741(5) 0.0195(3) Uani 1 1 d
F2 F -0.20735(11) 0.8185(4) 0.14831(5) 0.0264(4) Uani 1 1 d
F3 F -0.15323(12) 0.7237(4) 0.24468(5) 0.0298(4) Uani 1 1 d
F4 F 0.05111(12) 0.4090(4) 0.27848(5) 0.0272(4) Uani 1 1 d
F5 F 0.20027(11) 0.2033(4) 0.21815(5) 0.0197(3) Uani 1 1 d
N1 N 0.12954(15) 0.1692(5) 0.07601(6) 0.0124(4) Uani 1 1 d
N2 N 0.27724(15) 0.4147(5) 0.13426(6) 0.0137(4) Uani 1 1 d
C1 C 0.21061(18) 0.0883(6) 0.04692(8) 0.0115(5) Uani 1 1 d
C2 C 0.17813(19) -0.0772(6) 0.00147(8) 0.0134(5) Uani 1 1 d
H2 H 0.101(2) -0.124(6) -0.0072(9) 0.016 Uiso 1 1 d
C3 C 0.25927(19) -0.1547(6) -0.02789(8) 0.0124(5) Uani 1 1 d
H3 H 0.235(2) -0.276(7) -0.0590(9) 0.015 Uiso 1 1 d
C4 C 0.38076(18) -0.0801(6) -0.01518(8) 0.0109(5) Uani 1 1 d
C5 C 0.41531(18) 0.0816(5) 0.03002(8) 0.0105(4) Uani 1 1 d
C6 C 0.32953(18) 0.1642(6) 0.06058(8) 0.0107(4) Uani 1 1 d
C7 C 0.35896(18) 0.3289(6) 0.10565(8) 0.0123(5) Uani 1 1 d
C8 C 0.47838(19) 0.4061(6) 0.12092(8) 0.0136(5) Uani 1 1 d
H8 H 0.497(2) 0.516(7) 0.1520(9) 0.016 Uiso 1 1 d
C9 C 0.56039(18) 0.3252(6) 0.09198(8) 0.0127(5) Uani 1 1 d
H9 H 0.643(2) 0.381(6) 0.1032(8) 0.015 Uiso 1 1 d
C10 C 0.53322(18) 0.1610(6) 0.04580(8) 0.0116(5) Uani 1 1 d
C21 C 0.16825(19) 0.3277(6) 0.11763(8) 0.0134(5) Uani 1 1 d
C23 C 0.08010(18) 0.4196(6) 0.15033(8) 0.0125(5) Uani 1 1 d
C24 C -0.02751(18) 0.5677(6) 0.13421(8) 0.0138(5) Uani 1 1 d
C25 C -0.10581(19) 0.6692(6) 0.16561(9) 0.0183(5) Uani 1 1 d
C26 C -0.0782(2) 0.6194(6) 0.21411(9) 0.0206(5) Uani 1 1 d
C27 C 0.0261(2) 0.4666(6) 0.23123(8) 0.0165(5) Uani 1 1 d
C28 C 0.10313(18) 0.3678(6) 0.19963(8) 0.0138(5) 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'
F F 0.0171 0.0103 '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'
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
C21 N1 C1 116.07(18) . .
C21 N2 C7 115.87(19) . .
N1 C1 C6 121.1(2) . .
N1 C1 C2 120.45(19) . .
C6 C1 C2 118.43(19) . .
C3 C2 C1 120.4(2) . .
C3 C2 H2 121.5(15) . .
C1 C2 H2 118.1(15) . .
C2 C3 C4 122.6(2) . .
C2 C3 H3 119.0(14) . .
C4 C3 H3 118.4(14) . .
C5 C4 C10 118.98(19) . 3_655
C5 C4 C3 118.04(19) . .
C10 C4 C3 123.0(2) 3_655 .
C10 C5 C4 122.0(2) . .
C10 C5 C6 118.9(2) . .
C4 C5 C6 119.10(19) . .
C7 C6 C1 117.13(19) . .
C7 C6 C5 121.43(19) . .
C1 C6 C5 121.4(2) . .
N2 C7 C6 121.48(19) . .
N2 C7 C8 119.8(2) . .
C6 C7 C8 118.74(19) . .
C9 C8 C7 119.9(2) . .
C9 C8 H8 122.7(14) . .
C7 C8 H8 117.4(14) . .
C8 C9 C10 122.7(2) . .
C8 C9 H9 118.7(14) . .
C10 C9 H9 118.6(14) . .
C5 C10 C4 119.1(2) . 3_655
C5 C10 C9 118.27(19) . .
C4 C10 C9 122.67(19) 3_655 .
N2 C21 N1 128.3(2) . .
N2 C21 C23 114.72(19) . .
N1 C21 C23 116.96(19) . .
C24 C23 C28 116.1(2) . .
C24 C23 C21 123.0(2) . .
C28 C23 C21 120.90(19) . .
F1 C24 C25 117.0(2) . .
F1 C24 C23 121.0(2) . .
C25 C24 C23 122.0(2) . .
F2 C25 C26 120.6(2) . .
F2 C25 C24 119.6(2) . .
C26 C25 C24 119.8(2) . .
F3 C26 C27 120.3(2) . .
F3 C26 C25 119.8(2) . .
C27 C26 C25 119.9(2) . .
F4 C27 C26 119.6(2) . .
F4 C27 C28 120.7(2) . .
C26 C27 C28 119.7(2) . .
F5 C28 C27 116.9(2) . .
F5 C28 C23 120.47(19) . .
C27 C28 C23 122.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C24 1.339(3) .
F2 C25 1.342(3) .
F3 C26 1.348(3) .
F4 C27 1.341(3) .
F5 C28 1.334(2) .
N1 C21 1.339(3) .
N1 C1 1.349(3) .
N2 C21 1.336(3) .
N2 C7 1.350(3) .
C1 C6 1.417(3) .
C1 C2 1.427(3) .
C2 C3 1.352(3) .
C2 H2 0.91(2) .
C3 C4 1.440(3) .
C3 H3 0.99(2) .
C4 C5 1.420(3) .
C4 C10 1.423(3) 3_655
C5 C10 1.419(3) .
C5 C6 1.421(3) .
C6 C7 1.412(3) .
C7 C8 1.431(3) .
C8 C9 1.355(3) .
C8 H8 0.96(3) .
C9 C10 1.435(3) .
C9 H9 1.00(2) .
C10 C4 1.423(3) 3_655
C21 C23 1.491(3) .
C23 C24 1.392(3) .
C23 C28 1.392(3) .
C24 C25 1.389(3) .
C25 C26 1.374(3) .
C26 C27 1.372(3) .
C27 C28 1.380(3) .
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_4
C21 N1 C1 C6 0.9(3) . .
C21 N1 C1 C2 -179.24(19) . .
N1 C1 C2 C3 179.3(2) . .
C6 C1 C2 C3 -0.8(3) . .
C1 C2 C3 C4 0.6(3) . .
C2 C3 C4 C5 -0.1(3) . .
C2 C3 C4 C10 179.9(2) . 3_655
C10 C4 C5 C10 -0.8(3) 3_655 .
C3 C4 C5 C10 179.3(2) . .
C10 C4 C5 C6 179.71(19) 3_655 .
C3 C4 C5 C6 -0.3(3) . .
N1 C1 C6 C7 -0.3(3) . .
C2 C1 C6 C7 179.80(19) . .
N1 C1 C6 C5 -179.65(19) . .
C2 C1 C6 C5 0.5(3) . .
C10 C5 C6 C7 1.2(3) . .
C4 C5 C6 C7 -179.2(2) . .
C10 C5 C6 C1 -179.5(2) . .
C4 C5 C6 C1 0.1(3) . .
C21 N2 C7 C6 1.2(3) . .
C21 N2 C7 C8 -178.9(2) . .
C1 C6 C7 N2 -0.8(3) . .
C5 C6 C7 N2 178.54(19) . .
C1 C6 C7 C8 179.31(19) . .
C5 C6 C7 C8 -1.3(3) . .
N2 C7 C8 C9 -179.0(2) . .
C6 C7 C8 C9 0.9(3) . .
C7 C8 C9 C10 -0.2(3) . .
C4 C5 C10 C4 0.8(3) . 3_655
C6 C5 C10 C4 -179.71(19) . 3_655
C4 C5 C10 C9 179.90(19) . .
C6 C5 C10 C9 -0.6(3) . .
C8 C9 C10 C5 0.1(3) . .
C8 C9 C10 C4 179.2(2) . 3_655
C7 N2 C21 N1 -0.6(3) . .
C7 N2 C21 C23 178.97(18) . .
C1 N1 C21 N2 -0.4(3) . .
C1 N1 C21 C23 179.98(18) . .
N2 C21 C23 C24 138.1(2) . .
N1 C21 C23 C24 -42.3(3) . .
N2 C21 C23 C28 -40.4(3) . .
N1 C21 C23 C28 139.2(2) . .
C28 C23 C24 F1 -179.32(18) . .
C21 C23 C24 F1 2.1(3) . .
C28 C23 C24 C25 2.1(3) . .
C21 C23 C24 C25 -176.4(2) . .
F1 C24 C25 F2 -0.2(3) . .
C23 C24 C25 F2 178.5(2) . .
F1 C24 C25 C26 -179.5(2) . .
C23 C24 C25 C26 -0.9(3) . .
F2 C25 C26 F3 -0.5(3) . .
C24 C25 C26 F3 178.8(2) . .
F2 C25 C26 C27 -179.9(2) . .
C24 C25 C26 C27 -0.6(3) . .
F3 C26 C27 F4 2.5(3) . .
C25 C26 C27 F4 -178.0(2) . .
F3 C26 C27 C28 -178.7(2) . .
C25 C26 C27 C28 0.8(3) . .
F4 C27 C28 F5 2.2(3) . .
C26 C27 C28 F5 -176.5(2) . .
F4 C27 C28 C23 179.4(2) . .
C26 C27 C28 C23 0.6(3) . .
C24 C23 C28 F5 175.05(19) . .
C21 C23 C28 F5 -6.4(3) . .
C24 C23 C28 C27 -2.0(3) . .
C21 C23 C28 C27 176.6(2) . .
