# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Bis(4-fluorophenyl)-N,N'-di(n-butyl) quinaridonediimine ; _chemical_name_common ; N,N-Bis(4-fluorophenyl)-N,N'-di(n-butyl) quinaridonediimine ; _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 F2 N4' _chemical_formula_sum 'C40 H36 F2 N4' _chemical_formula_weight 610.73 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1105(14) _cell_length_b 9.868(2) _cell_length_c 12.576(3) _cell_angle_alpha 73.23(3) _cell_angle_beta 78.56(3) _cell_angle_gamma 70.79(3) _cell_volume 792.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 263(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 263(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7761 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3580 _reflns_number_gt 2728 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.0772P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3580 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 F1 F 1.15775(17) -0.19158(13) 0.03173(12) 0.0960(5) Uani 1 1 d . . . N1 N -0.07131(16) 0.23519(12) 0.31033(9) 0.0378(3) Uani 1 1 d . . . N2 N 0.46880(17) -0.09491(12) 0.32550(10) 0.0433(3) Uani 1 1 d . . . C1 C 0.2139(2) 0.43773(15) 0.08033(12) 0.0442(3) Uani 1 1 d . . . H1 H 0.1910 0.5288 0.0286 0.053 Uiso 1 1 calc R . . C2 C 0.4038(2) 0.33910(15) 0.08046(12) 0.0444(3) Uani 1 1 d . . . H2 H 0.5082 0.3630 0.0287 0.053 Uiso 1 1 calc R . . C3 C 0.4371(2) 0.20538(14) 0.15762(11) 0.0391(3) Uani 1 1 d . . . H3 H 0.5658 0.1400 0.1580 0.047 Uiso 1 1 calc R . . C4 C 0.28268(19) 0.16447(13) 0.23596(10) 0.0333(3) Uani 1 1 d . . . C5 C 0.08855(19) 0.26610(14) 0.23469(10) 0.0348(3) Uani 1 1 d . . . C6 C 0.0589(2) 0.40295(14) 0.15553(11) 0.0415(3) Uani 1 1 d . . . H6 H -0.0680 0.4709 0.1543 0.050 Uiso 1 1 calc R . . C7 C 0.31683(18) 0.02194(13) 0.32019(10) 0.0339(3) Uani 1 1 d . . . C8 C 0.15414(18) 0.01392(13) 0.41276(10) 0.0336(3) Uani 1 1 d . . . C9 C -0.03605(19) 0.11869(13) 0.40473(10) 0.0342(3) Uani 1 1 d . . . C10 C -0.18656(19) 0.10180(13) 0.49264(11) 0.0367(3) Uani 1 1 d . . . H10 H -0.3128 0.1702 0.4878 0.044 Uiso 1 1 calc R . . C11 C -0.27834(19) 0.32393(15) 0.29234(11) 0.0399(3) Uani 1 1 d . . . H11A H -0.3648 0.2601 0.3214 0.048 Uiso 1 1 calc R . . H11B H -0.2862 0.3606 0.2125 0.048 Uiso 1 1 calc R . . C12 C -0.3582(2) 0.45469(16) 0.34615(13) 0.0487(4) Uani 1 1 d . . . H12A H -0.3452 0.4196 0.4255 0.058 Uiso 1 1 calc R . . H12B H -0.2779 0.5224 0.3140 0.058 Uiso 1 1 calc R . . C13 C -0.5762(3) 0.5368(2) 0.33003(17) 0.0697(5) Uani 1 1 d . . . H13A H -0.6120 0.6279 0.3541 0.084 Uiso 1 1 calc R . . H13B H -0.5903 0.5633 0.2509 0.084 Uiso 1 1 calc R . . C14 C -0.7209(3) 0.4514(3) 0.3921(2) 0.0940(8) Uani 1 1 d . . . H14A H -0.7054 0.3721 0.3584 0.141 Uiso 1 1 calc R . . H14B H -0.8554 0.5159 0.3890 0.141 Uiso 1 1 calc R . . H14C H -0.6945 0.4116 0.4687 0.141 Uiso 1 1 calc R . . C15 C 0.64054(19) -0.11523(13) 0.24725(12) 0.0393(3) Uani 1 1 d . . . C16 C 0.8216(2) -0.12245(17) 0.27777(15) 0.0530(4) Uani 1 1 d . . . H16 H 0.8259 -0.1107 0.3479 0.064 Uiso 1 1 calc R . . C17 C 0.9952(2) -0.14685(19) 0.20492(17) 0.0624(5) Uani 1 1 d . . . H17 H 1.1158 -0.1490 0.2244 0.075 Uiso 1 1 calc R . . C18 C 0.9863(2) -0.16768(17) 0.10434(16) 0.0604(5) Uani 1 1 d . . . C19 C 0.8133(3) -0.16725(17) 0.07265(15) 0.0583(4) Uani 1 1 d . . . H19 H 0.8129 -0.1843 0.0037 0.070 Uiso 1 1 calc R . . C20 C 0.6383(2) -0.14092(16) 0.14496(13) 0.0490(4) Uani 1 1 d . . . H20 H 0.5191 -0.1405 0.1248 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0642(7) 0.0754(7) 0.1228(11) -0.0337(7) 0.0570(7) -0.0175(6) N1 0.0301(6) 0.0399(6) 0.0338(6) -0.0021(4) -0.0010(4) -0.0049(4) N2 0.0358(6) 0.0385(6) 0.0434(7) -0.0060(5) 0.0069(5) -0.0049(5) C1 0.0495(8) 0.0382(7) 0.0391(7) 0.0009(5) -0.0036(6) -0.0152(6) C2 0.0431(8) 0.0435(7) 0.0438(8) -0.0055(6) 0.0063(6) -0.0198(6) C3 0.0342(7) 0.0365(6) 0.0437(7) -0.0088(5) 0.0028(5) -0.0114(5) C4 0.0339(6) 0.0341(6) 0.0317(6) -0.0087(5) 0.0001(5) -0.0112(5) C5 0.0351(7) 0.0370(6) 0.0301(6) -0.0069(5) -0.0003(5) -0.0108(5) C6 0.0388(7) 0.0391(7) 0.0380(7) -0.0028(5) -0.0033(6) -0.0065(6) C7 0.0306(6) 0.0359(6) 0.0336(6) -0.0099(5) 0.0015(5) -0.0094(5) C8 0.0310(6) 0.0336(6) 0.0332(6) -0.0085(5) 0.0019(5) -0.0080(5) C9 0.0340(7) 0.0333(6) 0.0311(6) -0.0057(5) -0.0003(5) -0.0082(5) C10 0.0306(6) 0.0351(6) 0.0367(7) -0.0065(5) 0.0009(5) -0.0040(5) C11 0.0345(7) 0.0450(7) 0.0350(7) -0.0055(5) -0.0050(5) -0.0077(6) C12 0.0491(9) 0.0442(8) 0.0468(8) -0.0106(6) -0.0042(7) -0.0070(6) C13 0.0547(10) 0.0684(11) 0.0701(12) -0.0268(9) -0.0127(9) 0.0150(8) C14 0.0476(11) 0.129(2) 0.127(2) -0.0827(17) 0.0041(12) -0.0165(12) C15 0.0337(7) 0.0304(6) 0.0443(8) -0.0061(5) 0.0057(6) -0.0051(5) C16 0.0412(8) 0.0556(9) 0.0570(10) -0.0141(7) -0.0028(7) -0.0085(7) C17 0.0337(8) 0.0591(9) 0.0859(13) -0.0144(9) 0.0025(8) -0.0103(7) C18 0.0429(9) 0.0409(8) 0.0812(12) -0.0178(8) 0.0290(8) -0.0090(7) C19 0.0669(11) 0.0517(9) 0.0557(10) -0.0245(7) 0.0193(8) -0.0219(8) C20 0.0446(8) 0.0504(8) 0.0520(9) -0.0169(7) 0.0065(7) -0.0167(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C18 1.3670(17) . ? N1 C5 1.3863(16) . ? N1 C9 1.3908(16) . ? N1 C11 1.4678(17) . ? N2 C7 1.2908(17) . ? N2 C15 1.4057(17) . ? C1 C6 1.3693(19) . ? C1 C2 1.380(2) . ? C1 H1 0.9300 . ? C2 C3 1.3731(19) . ? C2 H2 0.9300 . ? C3 C4 1.4045(17) . ? C3 H3 0.9300 . ? C4 C5 1.4142(19) . ? C4 C7 1.4753(18) . ? C5 C6 1.4068(18) . ? C6 H6 0.9300 . ? C7 C8 1.4739(17) . ? C8 C10 1.3871(18) 2_556 ? C8 C9 1.4078(18) . ? C9 C10 1.3917(18) . ? C10 C8 1.3871(18) 2_556 ? C10 H10 0.9300 . ? C11 C12 1.522(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.518(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.500(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.385(2) . ? C15 C16 1.389(2) . ? C16 C17 1.380(2) . ? C16 H16 0.9300 . ? C17 C18 1.355(3) . ? C17 H17 0.9300 . ? C18 C19 1.365(3) . ? C19 C20 1.385(2) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 _geom_angle_publ_flag C5 N1 C9 119.84(11) . . ? C5 N1 C11 120.89(11) . . ? C9 N1 C11 119.27(11) . . ? C7 N2 C15 126.50(11) . . ? C6 C1 C2 120.69(12) . . ? C6 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 119.42(13) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 121.94(13) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 118.14(12) . . ? C3 C4 C7 122.52(12) . . ? C5 C4 C7 119.32(11) . . ? N1 C5 C6 119.49(12) . . ? N1 C5 C4 121.73(11) . . ? C6 C5 C4 118.77(12) . . ? C1 C6 C5 121.03(13) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N2 C7 C8 115.69(11) . . ? N2 C7 C4 129.59(12) . . ? C8 C7 C4 114.71(11) . . ? C10 C8 C9 119.50(12) 2_556 . ? C10 C8 C7 119.50(11) 2_556 . ? C9 C8 C7 120.95(11) . . ? N1 C9 C10 121.31(11) . . ? N1 C9 C8 120.25(12) . . ? C10 C9 C8 118.44(11) . . ? C8 C10 C9 122.06(12) 2_556 . ? C8 C10 H10 119.0 2_556 . ? C9 C10 H10 119.0 . . ? N1 C11 C12 114.87(11) . . ? N1 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? N1 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 112.33(14) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 114.43(17) . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 119.05(14) . . ? C20 C15 N2 122.10(13) . . ? C16 C15 N2 118.61(14) . . ? C17 C16 C15 120.59(16) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 118.65(16) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 122.71(15) . . ? C17 C18 F1 118.89(17) . . ? C19 C18 F1 118.40(18) . . ? C18 C19 C20 118.80(16) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C19 C20 C15 120.11(15) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.6(2) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 C7 -179.26(12) . . . . ? C9 N1 C5 C6 -164.40(12) . . . . ? C11 N1 C5 C6 15.58(18) . . . . ? C9 N1 C5 C4 14.50(18) . . . . ? C11 N1 C5 C4 -165.53(11) . . . . ? C3 C4 C5 N1 -178.96(11) . . . . ? C7 C4 C5 N1 -0.27(18) . . . . ? C3 C4 C5 C6 -0.06(18) . . . . ? C7 C4 C5 C6 178.63(11) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? N1 C5 C6 C1 179.33(13) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? C15 N2 C7 C8 179.16(12) . . . . ? C15 N2 C7 C4 -2.2(2) . . . . ? C3 C4 C7 N2 -14.1(2) . . . . ? C5 C4 C7 N2 167.25(13) . . . . ? C3 C4 C7 C8 164.57(11) . . . . ? C5 C4 C7 C8 -14.05(16) . . . . ? N2 C7 C8 C10 11.83(17) . . . 2_556 ? C4 C7 C8 C10 -167.05(11) . . . 2_556 ? N2 C7 C8 C9 -165.65(12) . . . . ? C4 C7 C8 C9 15.47(17) . . . . ? C5 N1 C9 C10 167.43(12) . . . . ? C11 N1 C9 C10 -12.55(18) . . . . ? C5 N1 C9 C8 -13.09(18) . . . . ? C11 N1 C9 C8 166.93(11) . . . . ? C10 C8 C9 N1 -179.83(12) 2_556 . . . ? C7 C8 C9 N1 -2.35(18) . . . . ? C10 C8 C9 C10 -0.3(2) 2_556 . . . ? C7 C8 C9 C10 177.15(11) . . . . ? N1 C9 C10 C8 179.83(12) . . . 2_556 ? C8 C9 C10 C8 0.3(2) . . . 2_556 ? C5 N1 C11 C12 -91.73(15) . . . . ? C9 N1 C11 C12 88.24(15) . . . . ? N1 C11 C12 C13 -176.83(13) . . . . ? C11 C12 C13 C14 68.2(2) . . . . ? C7 N2 C15 C20 -75.12(19) . . . . ? C7 N2 C15 C16 110.58(17) . . . . ? C20 C15 C16 C17 3.5(2) . . . . ? N2 C15 C16 C17 177.98(13) . . . . ? C15 C16 C17 C18 -1.8(2) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C16 C17 C18 F1 179.85(14) . . . . ? C17 C18 C19 C20 1.6(3) . . . . ? F1 C18 C19 C20 -179.04(13) . . . . ? C18 C19 C20 C15 0.2(2) . . . . ? C16 C15 C20 C19 -2.7(2) . . . . ? N2 C15 C20 C19 -176.94(12) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.220 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 923157' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Diphenyl-N,N'-di(n-butyl)-2,9-difluoro quinacridonediimine ; _chemical_name_common ; N,N-Diphenyl-N,N'-di(n-butyl)-2,9-difluoro quinacridonediimine ; _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 F2 N4, C H2 Cl2 ' _chemical_formula_sum 'C41 H38 Cl2 F2 N4' _chemical_formula_weight 695.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.602(5) _cell_length_b 13.889(8) _cell_length_c 15.854(10) _cell_angle_alpha 70.40(2) _cell_angle_beta 79.41(2) _cell_angle_gamma 88.920(18) _cell_volume 1752.1(17) _cell_formula_units_Z 2 _cell_measurement_temperature 263(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 263(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13676 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6111 _reflns_number_gt 3853 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1477P)^2^+0.1939P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6111 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.2208 _refine_ls_wR_factor_gt 0.1935 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.8377(3) 0.5595(2) -0.0543(2) 0.0603(7) Uani 1 1 d . . . C2 C 0.7923(3) 0.5363(2) 0.0379(2) 0.0630(8) Uani 1 1 d . . . H2 H 0.8326 0.5760 0.0682 0.076 Uiso 1 1 calc R . . C3 C 0.6869(3) 0.4542(2) 0.0861(2) 0.0566(7) Uani 1 1 d . . . H3 H 0.6555 0.4367 0.1503 0.068 Uiso 1 1 calc R . . C4 C 0.6254(3) 0.39603(18) 0.04057(18) 0.0449(6) Uani 1 1 d . . . C5 C 0.6752(3) 0.42178(18) -0.05356(18) 0.0469(6) Uani 1 1 d . . . C6 C 0.7842(3) 0.5046(2) -0.1000(2) 0.0561(7) Uani 1 1 d . . . H6 H 0.8206 0.5223 -0.1638 0.067 Uiso 1 1 calc R . . C7 C 0.6117(3) 0.36702(18) -0.10574(18) 0.0463(6) Uani 1 1 d . . . C8 C 0.6073(4) 0.3767(2) -0.26178(19) 0.0630(8) Uani 1 1 d . . . C9 C 0.4733(5) 0.4135(3) -0.2953(3) 0.0837(10) Uani 1 1 d . . . H9 H 0.4000 0.4477 -0.2638 0.100 Uiso 1 1 calc R . . C10 C 0.4437(6) 0.4015(3) -0.3743(3) 0.1056(14) Uani 1 1 d . . . H10 H 0.3506 0.4274 -0.3965 0.127 Uiso 1 1 calc R . . C11 C 0.5474(7) 0.3529(3) -0.4200(3) 0.1064(15) Uani 1 1 d . . . H11 H 0.5280 0.3468 -0.4751 0.128 Uiso 1 1 calc R . . C12 C 0.6776(6) 0.3134(3) -0.3877(3) 0.1002(14) Uani 1 1 d . . . H12 H 0.7472 0.2774 -0.4192 0.120 Uiso 1 1 calc R . . C13 C 0.7113(5) 0.3245(3) -0.3087(2) 0.0831(10) Uani 1 1 d . . . H13 H 0.8039 0.2971 -0.2868 0.100 Uiso 1 1 calc R . . C14 C 0.4522(3) 0.2977(2) 0.18526(18) 0.0506(6) Uani 1 1 d . . . C15 C 0.5500(3) 0.2305(2) 0.25065(19) 0.0576(7) Uani 1 1 d . . . H15A H 0.5342 0.1584 0.2550 0.069 Uiso 1 1 calc R . . H15B H 0.6635 0.2506 0.2264 0.069 Uiso 1 1 calc R . . C16 C 0.5057(4) 0.2386(3) 0.3449(2) 0.0684(8) Uani 1 1 d . . . H16A H 0.5350 0.3085 0.3415 0.082 Uiso 1 1 calc R . . H16B H 0.3895 0.2280 0.3652 0.082 Uiso 1 1 calc R . . C17 C 0.5843(5) 0.1631(3) 0.4142(2) 0.0963(12) Uani 1 1 d . . . H17A H 0.5519 0.0935 0.4201 0.145 Uiso 1 1 calc R . . H17B H 0.5529 0.1733 0.4731 0.145 Uiso 1 1 calc R . . H17C H 0.6995 0.1731 0.3947 0.145 Uiso 1 1 calc R . . C18 C 0.4678(3) 0.25203(18) 0.04548(17) 0.0412(6) Uani 1 1 d . . . C19 C 0.3748(3) 0.16366(18) 0.09553(17) 0.0418(6) Uani 1 1 d . . . H19 H 0.3459 0.1478 0.1596 0.050 Uiso 1 1 calc R . . C20 C 0.3214(3) 0.09674(17) 0.05703(16) 0.0391(5) Uani 1 1 d . . . C21 C 0.3734(3) 0.11582(18) -0.03746(16) 0.0403(5) Uani 1 1 d . . . C22 C 0.4636(3) 0.20577(18) -0.08789(17) 0.0431(6) Uani 1 1 d . . . H22 H 0.4939 0.2213 -0.1519 0.052 Uiso 1 1 calc R . . C23 C 0.5118(3) 0.27427(17) -0.04955(16) 0.0416(6) Uani 1 1 d . . . C24 C 0.4007(3) 0.0647(2) -0.17558(18) 0.0484(6) Uani 1 1 d . . . C25 C 0.2836(3) 0.1143(2) -0.23579(19) 0.0592(7) Uani 1 1 d . . . H25A H 0.1773 0.0810 -0.2067 0.071 Uiso 1 1 calc R . . H25B H 0.2779 0.1873 -0.2412 0.071 Uiso 1 1 calc R . . C26 C 0.3277(4) 0.1067(3) -0.3300(2) 0.0801(10) Uani 1 1 d . . . H26A H 0.4344 0.1394 -0.3587 0.096 Uiso 1 1 calc R . . H26B H 0.3326 0.0336 -0.3245 0.096 Uiso 1 1 calc R . . C27 C 0.2132(5) 0.1563(4) -0.3902(3) 0.1215(17) Uani 1 1 d . . . H27A H 0.1073 0.1241 -0.3623 0.182 Uiso 1 1 calc R . . H27B H 0.2462 0.1479 -0.4498 0.182 Uiso 1 1 calc R . . H27C H 0.2111 0.2293 -0.3980 0.182 Uiso 1 1 calc R . . C28 C 0.2208(3) 0.00531(18) 0.11337(17) 0.0420(6) Uani 1 1 d . . . C29 C 0.1454(3) 0.0307(2) 0.25929(17) 0.0495(6) Uani 1 1 d . . . C30 C 0.0570(3) 0.1173(2) 0.2479(2) 0.0582(7) Uani 1 1 d . . . H30 H 0.0145 0.1457 0.1940 0.070 Uiso 1 1 calc R . . C31 C 0.0303(4) 0.1624(3) 0.3145(2) 0.0724(9) Uani 1 1 d . . . H31 H -0.0295 0.2220 0.3057 0.087 Uiso 1 1 calc R . . C32 C 0.0889(4) 0.1222(3) 0.3929(2) 0.0800(10) Uani 1 1 d . . . H32 H 0.0694 0.1531 0.4387 0.096 Uiso 1 1 calc R . . C33 C 0.1763(4) 0.0367(3) 0.4047(2) 0.0784(10) Uani 1 1 d . . . H33 H 0.2178 0.0088 0.4590 0.094 Uiso 1 1 calc R . . C34 C 0.2048(4) -0.0095(2) 0.33916(19) 0.0620(7) Uani 1 1 d . . . H34 H 0.2652 -0.0689 0.3486 0.074 Uiso 1 1 calc R . . C35 C 0.1883(3) -0.06445(18) 0.06544(17) 0.0422(6) Uani 1 1 d . . . C36 C 0.0964(3) -0.15456(19) 0.11498(19) 0.0507(6) Uani 1 1 d . . . H36 H 0.0597 -0.1714 0.1787 0.061 Uiso 1 1 calc R . . C37 C 0.0600(3) -0.2179(2) 0.0713(2) 0.0550(7) Uani 1 1 d . . . C38 C 0.1080(3) -0.1964(2) -0.0204(2) 0.0567(7) Uani 1 1 d . . . H38 H 0.0791 -0.2415 -0.0492 0.068 Uiso 1 1 calc R . . C39 C 0.1990(3) -0.1084(2) -0.07021(19) 0.0518(6) Uani 1 1 d . . . H39 H 0.2330 -0.0929 -0.1340 0.062 Uiso 1 1 calc R . . C40 C 0.2428(3) -0.04063(18) -0.02847(17) 0.0434(6) Uani 1 1 d . . . C41 C 0.0067(9) 0.4764(5) 0.3637(5) 0.175(3) Uani 1 1 d . . . H41A H -0.0516 0.5196 0.3964 0.210 Uiso 1 1 calc R . . H41B H 0.0797 0.5222 0.3099 0.210 Uiso 1 1 calc R . . Cl1 Cl -0.1210(2) 0.41956(14) 0.32823(17) 0.1793(9) Uani 1 1 d . . . Cl2 Cl 0.1195(3) 0.39175(17) 0.4363(2) 0.2276(11) Uani 1 1 d . . . F1 F 0.9412(2) 0.64117(13) -0.10115(14) 0.0853(6) Uani 1 1 d . . . F2 F -0.0293(2) -0.30538(13) 0.12089(13) 0.0804(6) Uani 1 1 d . . . N1 N 0.5160(2) 0.31527(16) 0.08884(14) 0.0466(5) Uani 1 1 d . . . N2 N 0.6521(3) 0.40584(18) -0.19277(16) 0.0639(7) Uani 1 1 d . . . N3 N 0.1576(3) -0.02380(16) 0.19881(15) 0.0529(6) Uani 1 1 d . . . N4 N 0.3373(2) 0.04700(15) -0.07854(13) 0.0440(5) Uani 1 1 d . . . H14B H 0.442(3) 0.363(2) 0.1922(18) 0.052(7) Uiso 1 1 d . . . H14A H 0.339(3) 0.2713(19) 0.1997(17) 0.048(7) Uiso 1 1 d . . . H24B H 0.428(3) 0.0007(19) -0.1792(16) 0.042(6) Uiso 1 1 d . . . H24A H 0.506(3) 0.1049(19) -0.1920(17) 0.048(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0579(16) 0.0407(15) 0.081(2) -0.0142(15) -0.0220(15) -0.0120(12) C2 0.0648(17) 0.0494(16) 0.090(2) -0.0342(16) -0.0322(16) -0.0026(14) C3 0.0611(16) 0.0495(16) 0.0712(19) -0.0298(15) -0.0242(14) -0.0002(13) C4 0.0477(13) 0.0381(13) 0.0543(15) -0.0179(12) -0.0183(11) 0.0008(11) C5 0.0472(13) 0.0387(13) 0.0569(16) -0.0147(12) -0.0176(11) 0.0004(11) C6 0.0576(15) 0.0435(14) 0.0666(18) -0.0141(13) -0.0181(13) -0.0047(12) C7 0.0509(13) 0.0401(13) 0.0486(15) -0.0127(12) -0.0153(11) -0.0026(11) C8 0.089(2) 0.0501(16) 0.0447(16) -0.0063(13) -0.0152(15) -0.0195(15) C9 0.105(3) 0.081(2) 0.079(2) -0.035(2) -0.037(2) 0.005(2) C10 0.152(4) 0.090(3) 0.094(3) -0.035(3) -0.064(3) 0.009(3) C11 0.182(5) 0.078(3) 0.065(2) -0.019(2) -0.045(3) -0.012(3) C12 0.153(4) 0.073(2) 0.071(3) -0.031(2) 0.003(3) -0.015(3) C13 0.110(3) 0.071(2) 0.067(2) -0.0215(18) -0.0151(19) -0.005(2) C14 0.0577(16) 0.0514(16) 0.0515(16) -0.0283(13) -0.0108(12) -0.0013(13) C15 0.0637(16) 0.0629(17) 0.0526(16) -0.0256(14) -0.0159(13) 0.0035(14) C16 0.0717(18) 0.087(2) 0.0540(17) -0.0320(17) -0.0125(14) -0.0063(17) C17 0.099(3) 0.131(3) 0.053(2) -0.022(2) -0.0161(18) 0.003(2) C18 0.0428(12) 0.0399(13) 0.0483(14) -0.0205(11) -0.0163(11) 0.0013(10) C19 0.0440(12) 0.0446(13) 0.0401(13) -0.0174(11) -0.0102(10) -0.0003(11) C20 0.0383(11) 0.0405(13) 0.0423(13) -0.0160(11) -0.0129(10) 0.0005(10) C21 0.0423(12) 0.0408(13) 0.0423(13) -0.0166(11) -0.0137(10) -0.0011(10) C22 0.0501(13) 0.0432(13) 0.0380(13) -0.0146(11) -0.0117(10) -0.0017(11) C23 0.0446(12) 0.0370(12) 0.0445(14) -0.0129(11) -0.0135(10) -0.0003(10) C24 0.0517(15) 0.0528(16) 0.0480(15) -0.0259(13) -0.0106(12) 0.0027(13) C25 0.0664(17) 0.0620(17) 0.0518(16) -0.0184(14) -0.0194(13) 0.0040(14) C26 0.088(2) 0.108(3) 0.0521(18) -0.0333(19) -0.0206(16) -0.005(2) C27 0.110(3) 0.182(5) 0.061(2) -0.014(3) -0.035(2) -0.037(3) C28 0.0418(12) 0.0433(13) 0.0438(14) -0.0159(11) -0.0128(10) 0.0011(10) C29 0.0518(14) 0.0557(15) 0.0398(14) -0.0166(12) -0.0034(11) -0.0153(12) C30 0.0593(15) 0.0652(18) 0.0546(16) -0.0244(14) -0.0137(13) -0.0013(14) C31 0.0667(18) 0.079(2) 0.079(2) -0.0428(19) -0.0013(16) -0.0033(16) C32 0.088(2) 0.103(3) 0.058(2) -0.047(2) 0.0034(17) -0.018(2) C33 0.095(2) 0.099(3) 0.0425(17) -0.0214(18) -0.0174(16) -0.021(2) C34 0.0684(17) 0.0640(18) 0.0506(16) -0.0137(14) -0.0137(13) -0.0081(14) C35 0.0400(12) 0.0403(13) 0.0505(15) -0.0183(11) -0.0130(10) -0.0005(10) C36 0.0483(13) 0.0465(14) 0.0574(16) -0.0184(13) -0.0079(12) -0.0044(12) C37 0.0548(15) 0.0434(14) 0.0697(19) -0.0209(14) -0.0137(13) -0.0107(12) C38 0.0617(16) 0.0477(15) 0.073(2) -0.0309(15) -0.0230(14) -0.0029(13) C39 0.0582(15) 0.0510(15) 0.0555(16) -0.0264(13) -0.0175(12) -0.0022(12) C40 0.0445(12) 0.0428(13) 0.0489(15) -0.0194(12) -0.0155(11) -0.0007(11) C41 0.181(6) 0.112(4) 0.219(8) -0.064(5) 0.013(6) -0.026(4) Cl1 0.1385(12) 0.1518(15) 0.266(2) -0.1069(16) -0.0150(14) 0.0040(11) Cl2 0.204(2) 0.1573(17) 0.315(3) -0.0579(19) -0.078(2) 0.0336(16) F1 0.0963(13) 0.0556(10) 0.1021(15) -0.0188(10) -0.0257(11) -0.0324(9) F2 0.0916(12) 0.0577(10) 0.0895(13) -0.0271(10) -0.0026(10) -0.0351(9) N1 0.0521(11) 0.0456(12) 0.0482(12) -0.0218(10) -0.0128(9) -0.0056(10) N2 0.0835(16) 0.0549(14) 0.0497(14) -0.0095(11) -0.0166(12) -0.0236(12) N3 0.0624(13) 0.0515(13) 0.0458(13) -0.0185(10) -0.0068(10) -0.0124(10) N4 0.0529(11) 0.0437(11) 0.0412(11) -0.0199(10) -0.0121(9) -0.0046(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.350(4) . ? C1 F1 1.364(3) . ? C1 C2 1.368(5) . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? C3 C4 1.416(3) . ? C3 H3 0.9500 . ? C4 N1 1.389(3) . ? C4 C5 1.397(4) . ? C5 C6 1.401(4) . ? C5 C7 1.472(3) . ? C6 H6 0.9500 . ? C7 N2 1.283(3) . ? C7 C23 1.477(3) . ? C8 C9 1.376(5) . ? C8 N2 1.403(4) . ? C8 C13 1.404(5) . ? C9 C10 1.385(5) . ? C9 H9 0.9500 . ? C10 C11 1.358(7) . ? C10 H10 0.9500 . ? C11 C12 1.348(6) . ? C11 H11 0.9500 . ? C12 C13 1.393(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N1 1.464(3) . ? C14 C15 1.515(4) . ? C14 H14B 0.95(3) . ? C14 H14A 1.01(3) . ? C15 C16 1.514(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.495(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.388(3) . ? C18 N1 1.393(3) . ? C18 C23 1.411(4) . ? C19 C20 1.396(3) . ? C19 H19 0.9500 . ? C20 C21 1.416(3) . ? C20 C28 1.468(3) . ? C21 N4 1.392(3) . ? C21 C22 1.393(3) . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C24 N4 1.472(3) . ? C24 C25 1.512(4) . ? C24 H24B 0.93(2) . ? C24 H24A 1.02(3) . ? C25 C26 1.510(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.495(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 N3 1.290(3) . ? C28 C35 1.475(3) . ? C29 C34 1.389(4) . ? C29 C30 1.389(4) . ? C29 N3 1.397(3) . ? C30 C31 1.382(4) . ? C30 H30 0.9500 . ? C31 C32 1.365(5) . ? C31 H31 0.9500 . ? C32 C33 1.371(5) . ? C32 H32 0.9500 . ? C33 C34 1.378(4) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.399(3) . ? C35 C40 1.402(4) . ? C36 C37 1.360(4) . ? C36 H36 0.9500 . ? C37 F2 1.362(3) . ? C37 C38 1.366(4) . ? C38 C39 1.375(4) . ? C38 H38 0.9500 . ? C39 C40 1.410(3) . ? C39 H39 0.9500 . ? C40 N4 1.387(3) . ? C41 Cl1 1.645(7) . ? C41 Cl2 1.763(8) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? 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 _geom_angle_publ_flag C6 C1 F1 119.3(3) . . ? C6 C1 C2 122.4(3) . . ? F1 C1 C2 118.3(2) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N1 C4 C5 120.7(2) . . ? N1 C4 C3 120.3(2) . . ? C5 C4 C3 119.0(2) . . ? C6 C5 C4 118.9(2) . . ? C6 C5 C7 119.2(2) . . ? C4 C5 C7 121.8(2) . . ? C1 C6 C5 120.3(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N2 C7 C5 115.7(2) . . ? N2 C7 C23 129.6(2) . . ? C5 C7 C23 114.7(2) . . ? C9 C8 N2 120.4(3) . . ? C9 C8 C13 118.1(3) . . ? N2 C8 C13 120.6(3) . . ? C8 C9 C10 120.9(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 120.4(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.8(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 119.5(4) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? N1 C14 C15 114.6(2) . . ? N1 C14 H14B 107.0(16) . . ? C15 C14 H14B 110.7(16) . . ? N1 C14 H14A 109.0(14) . . ? C15 C14 H14A 112.3(15) . . ? H14B C14 H14A 102(2) . . ? C16 C15 C14 112.1(2) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 113.4(3) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N1 120.4(2) . . ? C19 C18 C23 117.7(2) . . ? N1 C18 C23 121.9(2) . . ? C18 C19 C20 123.7(2) . . ? C18 C19 H19 118.1 . . ? C20 C19 H19 118.1 . . ? C19 C20 C21 118.4(2) . . ? C19 C20 C28 121.2(2) . . ? C21 C20 C28 120.3(2) . . ? N4 C21 C22 121.0(2) . . ? N4 C21 C20 121.4(2) . . ? C22 C21 C20 117.5(2) . . ? C23 C22 C21 123.6(2) . . ? C23 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? C22 C23 C18 118.8(2) . . ? C22 C23 C7 121.4(2) . . ? C18 C23 C7 119.8(2) . . ? N4 C24 C25 112.4(2) . . ? N4 C24 H24B 105.7(15) . . ? C25 C24 H24B 112.2(15) . . ? N4 C24 H24A 107.5(14) . . ? C25 C24 H24A 114.1(15) . . ? H24B C24 H24A 104(2) . . ? C26 C25 C24 112.6(2) . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C24 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C25 112.9(3) . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26B 109.0 . . ? C25 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C28 C20 129.7(2) . . ? N3 C28 C35 115.0(2) . . ? C20 C28 C35 115.3(2) . . ? C34 C29 C30 118.4(2) . . ? C34 C29 N3 119.5(3) . . ? C30 C29 N3 121.6(2) . . ? C31 C30 C29 120.4(3) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C32 C31 C30 120.7(3) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 119.2(3) . . ? C31 C32 H32 120.4 . . ? C33 C32 H32 120.4 . . ? C32 C33 C34 121.1(3) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C33 C34 C29 120.1(3) . . ? C33 C34 H34 120.0 . . ? C29 C34 H34 120.0 . . ? C36 C35 C40 119.8(2) . . ? C36 C35 C28 118.7(2) . . ? C40 C35 C28 121.5(2) . . ? C37 C36 C35 119.6(3) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C36 C37 F2 118.6(3) . . ? C36 C37 C38 122.4(2) . . ? F2 C37 C38 118.9(2) . . ? C37 C38 C39 118.8(2) . . ? C37 C38 H38 120.6 . . ? C39 C38 H38 120.6 . . ? C38 C39 C40 121.3(3) . . ? C38 C39 H39 119.3 . . ? C40 C39 H39 119.3 . . ? N4 C40 C35 120.8(2) . . ? N4 C40 C39 121.2(2) . . ? C35 C40 C39 118.0(2) . . ? Cl1 C41 Cl2 114.2(4) . . ? Cl1 C41 H41A 108.7 . . ? Cl2 C41 H41A 108.7 . . ? Cl1 C41 H41B 108.7 . . ? Cl2 C41 H41B 108.7 . . ? H41A C41 H41B 107.6 . . ? C4 N1 C18 120.0(2) . . ? C4 N1 C14 119.33(19) . . ? C18 N1 C14 120.6(2) . . ? C7 N2 C8 130.5(2) . . ? C28 N3 C29 129.0(2) . . ? C40 N4 C21 120.6(2) . . ? C40 N4 C24 118.57(19) . . ? C21 N4 C24 120.8(2) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.5(5) . . . . ? F1 C1 C2 C3 179.6(2) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 N1 -178.2(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? N1 C4 C5 C6 179.2(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? N1 C4 C5 C7 1.7(4) . . . . ? C3 C4 C5 C7 -177.7(2) . . . . ? F1 C1 C6 C5 -178.6(2) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C7 C5 C6 C1 176.5(2) . . . . ? C6 C5 C7 N2 -5.8(4) . . . . ? C4 C5 C7 N2 171.7(2) . . . . ? C6 C5 C7 C23 173.6(2) . . . . ? C4 C5 C7 C23 -8.9(3) . . . . ? N2 C8 C9 C10 167.6(3) . . . . ? C13 C8 C9 C10 -1.4(5) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 C12 1.9(7) . . . . ? C10 C11 C12 C13 -2.2(7) . . . . ? C11 C12 C13 C8 0.7(6) . . . . ? C9 C8 C13 C12 1.1(5) . . . . ? N2 C8 C13 C12 -168.0(3) . . . . ? N1 C14 C15 C16 164.2(2) . . . . ? C14 C15 C16 C17 172.3(3) . . . . ? N1 C18 C19 C20 179.8(2) . . . . ? C23 C18 C19 C20 -0.8(4) . . . . ? C18 C19 C20 C21 4.5(4) . . . . ? C18 C19 C20 C28 -178.9(2) . . . . ? C19 C20 C21 N4 173.7(2) . . . . ? C28 C20 C21 N4 -2.9(3) . . . . ? C19 C20 C21 C22 -5.7(3) . . . . ? C28 C20 C21 C22 177.6(2) . . . . ? N4 C21 C22 C23 -175.8(2) . . . . ? C20 C21 C22 C23 3.6(4) . . . . ? C21 C22 C23 C18 0.1(4) . . . . ? C21 C22 C23 C7 178.0(2) . . . . ? C19 C18 C23 C22 -1.6(3) . . . . ? N1 C18 C23 C22 177.9(2) . . . . ? C19 C18 C23 C7 -179.5(2) . . . . ? N1 C18 C23 C7 -0.1(4) . . . . ? N2 C7 C23 C22 9.4(4) . . . . ? C5 C7 C23 C22 -169.8(2) . . . . ? N2 C7 C23 C18 -172.7(3) . . . . ? C5 C7 C23 C18 8.0(3) . . . . ? N4 C24 C25 C26 -164.4(2) . . . . ? C24 C25 C26 C27 -179.5(3) . . . . ? C19 C20 C28 N3 5.9(4) . . . . ? C21 C20 C28 N3 -177.5(2) . . . . ? C19 C20 C28 C35 -173.4(2) . . . . ? C21 C20 C28 C35 3.2(3) . . . . ? C34 C29 C30 C31 0.5(4) . . . . ? N3 C29 C30 C31 171.8(2) . . . . ? C29 C30 C31 C32 -0.6(4) . . . . ? C30 C31 C32 C33 0.6(5) . . . . ? C31 C32 C33 C34 -0.4(5) . . . . ? C32 C33 C34 C29 0.3(5) . . . . ? C30 C29 C34 C33 -0.3(4) . . . . ? N3 C29 C34 C33 -171.8(3) . . . . ? N3 C28 C35 C36 -0.9(3) . . . . ? C20 C28 C35 C36 178.5(2) . . . . ? N3 C28 C35 C40 177.0(2) . . . . ? C20 C28 C35 C40 -3.6(3) . . . . ? C40 C35 C36 C37 -0.4(4) . . . . ? C28 C35 C36 C37 177.5(2) . . . . ? C35 C36 C37 F2 179.9(2) . . . . ? C35 C36 C37 C38 -1.0(4) . . . . ? C36 C37 C38 C39 1.2(4) . . . . ? F2 C37 C38 C39 -179.6(2) . . . . ? C37 C38 C39 C40 -0.1(4) . . . . ? C36 C35 C40 N4 -178.4(2) . . . . ? C28 C35 C40 N4 3.8(4) . . . . ? C36 C35 C40 C39 1.5(4) . . . . ? C28 C35 C40 C39 -176.4(2) . . . . ? C38 C39 C40 N4 178.6(2) . . . . ? C38 C39 C40 C35 -1.2(4) . . . . ? C5 C4 N1 C18 7.0(4) . . . . ? C3 C4 N1 C18 -173.6(2) . . . . ? C5 C4 N1 C14 -172.9(2) . . . . ? C3 C4 N1 C14 6.5(3) . . . . ? C19 C18 N1 C4 171.6(2) . . . . ? C23 C18 N1 C4 -7.8(3) . . . . ? C19 C18 N1 C14 -8.5(3) . . . . ? C23 C18 N1 C14 172.0(2) . . . . ? C15 C14 N1 C4 -87.5(3) . . . . ? C15 C14 N1 C18 92.6(3) . . . . ? C5 C7 N2 C8 -176.5(3) . . . . ? C23 C7 N2 C8 4.3(5) . . . . ? C9 C8 N2 C7 87.3(4) . . . . ? C13 C8 N2 C7 -103.9(4) . . . . ? C20 C28 N3 C29 11.3(4) . . . . ? C35 C28 N3 C29 -169.4(2) . . . . ? C34 C29 N3 C28 -124.4(3) . . . . ? C30 C29 N3 C28 64.3(4) . . . . ? C35 C40 N4 C21 -3.3(3) . . . . ? C39 C40 N4 C21 176.9(2) . . . . ? C35 C40 N4 C24 175.7(2) . . . . ? C39 C40 N4 C24 -4.1(3) . . . . ? C22 C21 N4 C40 -177.7(2) . . . . ? C20 C21 N4 C40 2.9(3) . . . . ? C22 C21 N4 C24 3.3(3) . . . . ? C20 C21 N4 C24 -176.1(2) . . . . ? C25 C24 N4 C40 83.7(3) . . . . ? C25 C24 N4 C21 -97.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C38 H38 F1 0.95 2.46 3.395(3) 166.2 1_445 C2 H2 F2 0.95 2.49 3.426(3) 169.7 1_665 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.331 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 923158' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Bis(4-fluorophenyl)-N,N'-di(n-butyl)-1,3,8,10- tetramethylquinacridonediimine ; _chemical_name_common ; N,N-Bis(4-fluorophenyl)-N,N'-di(n-butyl)-1,3,8,10- tetramethylquinacridonediimine ; _chemical_melting_point ? _chemical_formula_moiety 'C44 H44 F2 N4' _chemical_formula_sum 'C44 H44 F2 N4' _chemical_formula_weight 666.83 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.778(5) _cell_length_b 9.171(6) _cell_length_c 13.365(8) _cell_angle_alpha 71.67(3) _cell_angle_beta 72.14(2) _cell_angle_gamma 62.81(3) _cell_volume 891.3(10) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'pale red' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8855 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4050 _reflns_number_gt 2788 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0832P)^2^+0.1195P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4050 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1479 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.001 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 -0.0896(3) 0.8722(3) 0.46915(16) 0.0579(6) Uani 1 1 d . . . C2 C 0.0107(3) 0.7079(3) 0.46836(16) 0.0631(6) Uani 1 1 d . . . H2 H -0.0026 0.6240 0.5296 0.076 Uiso 1 1 calc R . . C3 C 0.1325(3) 0.6647(3) 0.37695(15) 0.0552(5) Uani 1 1 d . . . H3 H 0.2037 0.5499 0.3758 0.066 Uiso 1 1 calc R . . C4 C 0.1528(2) 0.7857(2) 0.28689(13) 0.0391(4) Uani 1 1 d . . . C5 C 0.0481(3) 0.9523(3) 0.29087(16) 0.0474(5) Uani 1 1 d . . . H5 H 0.0599 1.0373 0.2301 0.057 Uiso 1 1 calc R . . C6 C -0.0737(3) 0.9963(3) 0.38261(17) 0.0585(6) Uani 1 1 d . . . H6 H -0.1449 1.1106 0.3853 0.070 Uiso 1 1 calc R . . C7 C 0.2937(2) 0.7819(2) 0.10229(13) 0.0317(4) Uani 1 1 d . . . C8 C 0.4618(2) 0.7322(2) 0.02664(13) 0.0317(4) Uani 1 1 d . . . C9 C 0.6063(2) 0.5793(2) 0.04943(13) 0.0348(4) Uani 1 1 d . . . C10 C 0.5971(2) 0.4468(2) 0.14897(15) 0.0432(4) Uani 1 1 d . . . H10A H 0.6946 0.3399 0.1384 0.065 Uiso 1 1 calc R . . H10B H 0.4865 0.4348 0.1633 0.065 Uiso 1 1 calc R . . H10C H 0.6040 0.4794 0.2101 0.065 Uiso 1 1 calc R . . C11 C 0.7609(2) 0.5477(2) -0.02478(14) 0.0392(4) Uani 1 1 d . . . H11 H 0.8571 0.4442 -0.0105 0.047 Uiso 1 1 calc R . . C12 C 0.7808(2) 0.6623(2) -0.11998(14) 0.0395(4) Uani 1 1 d . . . C13 C 0.9493(3) 0.6169(3) -0.2007(2) 0.0561(5) Uani 1 1 d . . . C14 C 0.6411(2) 0.8119(2) -0.14153(14) 0.0379(4) Uani 1 1 d . . . H14 H 0.6546 0.8921 -0.2051 0.045 Uiso 1 1 calc R . . C15 C 0.4792(2) 0.8469(2) -0.07065(13) 0.0325(4) Uani 1 1 d . . . C16 C 0.16756(19) 1.0001(2) -0.04840(12) 0.0305(3) Uani 1 1 d . . . C17 C 0.0226(2) 1.1115(2) -0.09509(13) 0.0316(4) Uani 1 1 d . . . H17 H 0.0370 1.1899 -0.1596 0.038 Uiso 1 1 calc R . . C18 C 0.1420(2) 0.8896(2) 0.04952(13) 0.0307(3) Uani 1 1 d . . . C19 C 0.3596(2) 1.1335(2) -0.17991(14) 0.0376(4) Uani 1 1 d . . . H19A H 0.4691 1.1368 -0.1767 0.045 Uiso 1 1 calc R . . H19B H 0.2627 1.2385 -0.1619 0.045 Uiso 1 1 calc R . . C20 C 0.3679(3) 1.1319(3) -0.29524(15) 0.0492(5) Uani 1 1 d . . . H20A H 0.2526 1.1477 -0.3032 0.059 Uiso 1 1 calc R . . H20B H 0.4544 1.0222 -0.3122 0.059 Uiso 1 1 calc R . . C21 C 0.4197(4) 1.2714(4) -0.3732(2) 0.0898(9) Uani 1 1 d . . . H21A H 0.3283 1.3805 -0.3581 0.108 Uiso 1 1 calc R . . H21B H 0.5296 1.2600 -0.3595 0.108 Uiso 1 1 calc R . . C22 C 0.4444(4) 1.2733(5) -0.4877(2) 0.1148(13) Uani 1 1 d . . . H22A H 0.5336 1.1655 -0.5037 0.172 Uiso 1 1 calc R . . H22B H 0.4818 1.3633 -0.5319 0.172 Uiso 1 1 calc R . . H22C H 0.3340 1.2925 -0.5035 0.172 Uiso 1 1 calc R . . F1 F -0.2084(2) 0.9147(2) 0.55927(11) 0.0883(5) Uani 1 1 d . . . N1 N 0.29474(18) 0.73281(19) 0.20320(11) 0.0394(4) Uani 1 1 d . . . N2 N 0.33499(16) 0.99360(17) -0.09725(11) 0.0336(3) Uani 1 1 d . . . H13B H 0.951(3) 0.701(3) -0.2657(17) 0.047 Uiso 1 1 d . . . H13A H 1.038(3) 0.587(3) -0.1706(16) 0.047 Uiso 1 1 d . . . H13C H 0.969(3) 0.518(3) -0.2281(15) 0.047 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0494(12) 0.0878(17) 0.0377(10) -0.0227(11) 0.0044(9) -0.0301(12) C2 0.0625(14) 0.0786(17) 0.0370(10) -0.0018(10) -0.0028(10) -0.0295(13) C3 0.0498(12) 0.0569(13) 0.0410(10) -0.0005(9) -0.0069(9) -0.0135(10) C4 0.0295(8) 0.0543(11) 0.0335(9) -0.0067(8) -0.0093(7) -0.0163(8) C5 0.0503(11) 0.0525(11) 0.0436(10) -0.0132(9) -0.0036(9) -0.0253(10) C6 0.0555(13) 0.0642(14) 0.0586(13) -0.0297(11) 0.0004(10) -0.0225(11) C7 0.0258(8) 0.0345(9) 0.0347(8) -0.0061(7) -0.0078(6) -0.0114(7) C8 0.0241(8) 0.0367(9) 0.0353(8) -0.0085(7) -0.0088(6) -0.0103(7) C9 0.0295(8) 0.0368(9) 0.0388(9) -0.0078(7) -0.0114(7) -0.0110(7) C10 0.0372(10) 0.0403(10) 0.0446(10) -0.0029(8) -0.0124(8) -0.0102(8) C11 0.0264(8) 0.0375(9) 0.0474(10) -0.0100(8) -0.0094(7) -0.0052(7) C12 0.0260(8) 0.0433(10) 0.0462(10) -0.0133(8) -0.0041(7) -0.0105(7) C13 0.0326(11) 0.0567(13) 0.0598(13) -0.0109(11) 0.0007(10) -0.0086(10) C14 0.0259(8) 0.0421(10) 0.0421(9) -0.0065(8) -0.0037(7) -0.0139(7) C15 0.0232(8) 0.0355(9) 0.0377(8) -0.0083(7) -0.0070(7) -0.0098(7) C16 0.0234(8) 0.0334(8) 0.0350(8) -0.0078(7) -0.0056(6) -0.0112(6) C17 0.0260(8) 0.0336(8) 0.0331(8) -0.0046(7) -0.0067(6) -0.0111(7) C18 0.0233(7) 0.0324(8) 0.0346(8) -0.0078(7) -0.0067(6) -0.0084(6) C19 0.0281(8) 0.0355(9) 0.0469(10) -0.0016(7) -0.0071(7) -0.0153(7) C20 0.0352(10) 0.0592(12) 0.0441(10) 0.0012(9) -0.0079(8) -0.0188(9) C21 0.096(2) 0.104(2) 0.0616(16) 0.0177(15) -0.0165(15) -0.0557(19) C22 0.087(2) 0.138(3) 0.0724(19) 0.032(2) -0.0198(17) -0.038(2) F1 0.0772(10) 0.1266(14) 0.0512(8) -0.0382(9) 0.0190(7) -0.0393(10) N1 0.0286(7) 0.0492(9) 0.0348(7) -0.0058(6) -0.0076(6) -0.0119(7) N2 0.0222(7) 0.0346(7) 0.0390(7) -0.0026(6) -0.0061(6) -0.0102(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.355(4) . ? C1 F1 1.358(2) . ? C1 C6 1.368(3) . ? C2 C3 1.382(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 N1 1.404(2) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.282(2) . ? C7 C8 1.472(2) . ? C7 C18 1.477(2) . ? C8 C15 1.409(2) . ? C8 C9 1.418(2) . ? C9 C11 1.380(2) . ? C9 C10 1.504(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.395(3) . ? C11 H11 0.9500 . ? C12 C14 1.378(3) . ? C12 C13 1.505(3) . ? C13 H13B 0.97(2) . ? C13 H13A 0.88(2) . ? C13 H13C 1.01(2) . ? C14 C15 1.403(2) . ? C14 H14 0.9500 . ? C15 N2 1.399(2) . ? C16 N2 1.395(2) . ? C16 C17 1.396(2) . ? C16 C18 1.408(2) . ? C17 C18 1.389(2) 2_575 ? C17 H17 0.9500 . ? C18 C17 1.389(2) 2_575 ? C19 N2 1.459(2) . ? C19 C20 1.525(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.527(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.473(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 _geom_angle_publ_flag C2 C1 F1 118.8(2) . . ? C2 C1 C6 122.13(19) . . ? F1 C1 C6 119.1(2) . . ? C1 C2 C3 118.8(2) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.22(18) . . ? C3 C4 N1 117.39(18) . . ? C5 C4 N1 123.75(17) . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.9(2) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N1 C7 C8 118.27(15) . . ? N1 C7 C18 127.90(15) . . ? C8 C7 C18 113.80(14) . . ? C15 C8 C9 119.45(15) . . ? C15 C8 C7 117.42(14) . . ? C9 C8 C7 123.08(15) . . ? C11 C9 C8 118.66(16) . . ? C11 C9 C10 118.32(15) . . ? C8 C9 C10 122.97(15) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C12 122.30(16) . . ? C9 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C14 C12 C11 119.07(16) . . ? C14 C12 C13 120.93(18) . . ? C11 C12 C13 119.88(17) . . ? C12 C13 H13B 114.7(12) . . ? C12 C13 H13A 110.6(13) . . ? H13B C13 H13A 111.4(18) . . ? C12 C13 H13C 109.8(11) . . ? H13B C13 H13C 102.7(16) . . ? H13A C13 H13C 107.2(18) . . ? C12 C14 C15 120.75(17) . . ? C12 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? N2 C15 C14 120.19(16) . . ? N2 C15 C8 120.12(14) . . ? C14 C15 C8 119.68(15) . . ? N2 C16 C17 121.82(15) . . ? N2 C16 C18 119.92(14) . . ? C17 C16 C18 118.24(14) . . ? C18 C17 C16 121.59(16) 2_575 . ? C18 C17 H17 119.2 2_575 . ? C16 C17 H17 119.2 . . ? C17 C18 C16 120.12(14) 2_575 . ? C17 C18 C7 122.21(15) 2_575 . ? C16 C18 C7 117.63(14) . . ? N2 C19 C20 116.64(15) . . ? N2 C19 H19A 108.1 . . ? C20 C19 H19A 108.1 . . ? N2 C19 H19B 108.1 . . ? C20 C19 H19B 108.1 . . ? H19A C19 H19B 107.3 . . ? C19 C20 C21 110.3(2) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C20 114.8(3) . . ? C22 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? C22 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C7 N1 C4 126.57(15) . . ? C16 N2 C15 119.02(14) . . ? C16 N2 C19 120.54(13) . . ? C15 N2 C19 120.32(14) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 C3 -179.5(2) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 N1 171.63(19) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? N1 C4 C5 C6 -170.70(18) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? F1 C1 C6 C5 179.83(19) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? N1 C7 C8 C15 -145.87(16) . . . . ? C18 C7 C8 C15 32.3(2) . . . . ? N1 C7 C8 C9 31.5(2) . . . . ? C18 C7 C8 C9 -150.33(15) . . . . ? C15 C8 C9 C11 0.2(2) . . . . ? C7 C8 C9 C11 -177.09(15) . . . . ? C15 C8 C9 C10 -177.33(15) . . . . ? C7 C8 C9 C10 5.3(2) . . . . ? C8 C9 C11 C12 1.5(2) . . . . ? C10 C9 C11 C12 179.19(15) . . . . ? C9 C11 C12 C14 -0.7(3) . . . . ? C9 C11 C12 C13 -176.62(18) . . . . ? C11 C12 C14 C15 -1.9(3) . . . . ? C13 C12 C14 C15 173.97(18) . . . . ? C12 C14 C15 N2 -175.23(15) . . . . ? C12 C14 C15 C8 3.6(2) . . . . ? C9 C8 C15 N2 176.12(14) . . . . ? C7 C8 C15 N2 -6.4(2) . . . . ? C9 C8 C15 C14 -2.8(2) . . . . ? C7 C8 C15 C14 174.72(14) . . . . ? N2 C16 C17 C18 175.96(14) . . . 2_575 ? C18 C16 C17 C18 -2.6(3) . . . 2_575 ? N2 C16 C18 C17 -176.03(14) . . . 2_575 ? C17 C16 C18 C17 2.6(2) . . . 2_575 ? N2 C16 C18 C7 6.1(2) . . . . ? C17 C16 C18 C7 -175.28(14) . . . . ? N1 C7 C18 C17 -32.1(3) . . . 2_575 ? C8 C7 C18 C17 149.95(15) . . . 2_575 ? N1 C7 C18 C16 145.70(17) . . . . ? C8 C7 C18 C16 -32.2(2) . . . . ? N2 C19 C20 C21 -171.92(18) . . . . ? C19 C20 C21 C22 175.7(2) . . . . ? C8 C7 N1 C4 170.47(16) . . . . ? C18 C7 N1 C4 -7.4(3) . . . . ? C3 C4 N1 C7 138.91(19) . . . . ? C5 C4 N1 C7 -50.4(3) . . . . ? C17 C16 N2 C15 -157.06(15) . . . . ? C18 C16 N2 C15 21.5(2) . . . . ? C17 C16 N2 C19 19.0(2) . . . . ? C18 C16 N2 C19 -162.41(14) . . . . ? C14 C15 N2 C16 157.46(15) . . . . ? C8 C15 N2 C16 -21.4(2) . . . . ? C14 C15 N2 C19 -18.6(2) . . . . ? C8 C15 N2 C19 162.48(14) . . . . ? C20 C19 N2 C16 -87.92(19) . . . . ? C20 C19 N2 C15 88.12(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C22 H22A F1 0.98 2.51 3.349(4) 143.1 1_654 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.329 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 923159' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Bis(2,3,4,5,6-pentafluorophenyl)-N,N'- di(n-butyl)quinaridonediimine ; _chemical_name_common ; N,N-Bis(2,3,4,5,6-pentafluorophenyl)-N,N'- di(n-butyl)quinaridonediimine ; _chemical_melting_point ? _chemical_formula_moiety 'C40 H28 F10 N4' _chemical_formula_sum 'C40 H28 F10 N4' _chemical_formula_weight 754.66 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3925(15) _cell_length_b 9.2554(19) _cell_length_c 12.899(3) _cell_angle_alpha 88.42(3) _cell_angle_beta 75.51(3) _cell_angle_gamma 87.38(3) _cell_volume 853.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 263(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 386 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 263(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6758 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2979 _reflns_number_gt 2039 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0961P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2979 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1831 _refine_ls_wR_factor_gt 0.1677 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 F1 F 0.1359(3) -0.0398(2) 0.35096(17) 0.0852(6) Uani 1 1 d . . . F2 F 0.1910(4) -0.2565(2) 0.2124(3) 0.1403(11) Uani 1 1 d . . . F3 F 0.2675(5) -0.1994(4) -0.0030(3) 0.1890(17) Uani 1 1 d . . . F4 F 0.2827(5) 0.0769(4) -0.0753(2) 0.1703(14) Uani 1 1 d . . . F5 F 0.2251(4) 0.2940(3) 0.06393(16) 0.1137(8) Uani 1 1 d . . . N1 N 0.1264(3) 0.2510(2) 0.28066(17) 0.0538(6) Uani 1 1 d . . . N2 N 0.2773(3) 0.3237(2) 0.56009(16) 0.0496(5) Uani 1 1 d . . . C1 C 0.1801(3) 0.1348(3) 0.2122(2) 0.0551(7) Uani 1 1 d . . . C2 C 0.1732(4) -0.0079(3) 0.2452(3) 0.0635(8) Uani 1 1 d . . . C3 C 0.2010(5) -0.1199(4) 0.1742(4) 0.0918(12) Uani 1 1 d . . . C4 C 0.2395(6) -0.0909(6) 0.0661(4) 0.1136(17) Uani 1 1 d . . . C5 C 0.2470(6) 0.0474(6) 0.0314(3) 0.1056(14) Uani 1 1 d . . . C6 C 0.2168(5) 0.1598(4) 0.1017(3) 0.0774(9) Uani 1 1 d . . . C7 C 0.2006(3) 0.2829(3) 0.35785(19) 0.0451(6) Uani 1 1 d . . . C8 C 0.1016(3) 0.3967(3) 0.43001(19) 0.0452(6) Uani 1 1 d . . . C9 C 0.1390(3) 0.4113(3) 0.53076(19) 0.0455(6) Uani 1 1 d . . . C10 C 0.4058(3) 0.2458(3) 0.4827(2) 0.0454(6) Uani 1 1 d . . . C11 C 0.3734(3) 0.2248(2) 0.38055(19) 0.0452(6) Uani 1 1 d . . . C12 C 0.5142(3) 0.1546(3) 0.3024(2) 0.0518(6) Uani 1 1 d . . . H12 H 0.4964 0.1431 0.2343 0.062 Uiso 1 1 calc R . . C13 C 0.6772(4) 0.1025(3) 0.3244(2) 0.0607(7) Uani 1 1 d . . . H13 H 0.7694 0.0570 0.2715 0.073 Uiso 1 1 calc R . . C14 C 0.7038(4) 0.1181(3) 0.4258(2) 0.0601(7) Uani 1 1 d . . . H14 H 0.8130 0.0804 0.4413 0.072 Uiso 1 1 calc R . . C15 C 0.5717(4) 0.1884(3) 0.5039(2) 0.0546(7) Uani 1 1 d . . . H15 H 0.5923 0.1981 0.5715 0.066 Uiso 1 1 calc R . . C16 C -0.0351(3) 0.4840(3) 0.4011(2) 0.0497(6) Uani 1 1 d . . . H16 H -0.0584 0.4726 0.3343 0.060 Uiso 1 1 calc R . . C17 C 0.2928(4) 0.3248(3) 0.6713(2) 0.0520(6) Uani 1 1 d . . . H17A H 0.3459 0.2319 0.6881 0.062 Uiso 1 1 calc R . . H17B H 0.1682 0.3359 0.7183 0.062 Uiso 1 1 calc R . . C18 C 0.4107(4) 0.4425(3) 0.6944(2) 0.0650(8) Uani 1 1 d . . . H18A H 0.3712 0.5339 0.6667 0.078 Uiso 1 1 calc R . . H18B H 0.5401 0.4221 0.6572 0.078 Uiso 1 1 calc R . . C19 C 0.3970(6) 0.4568(5) 0.8134(3) 0.0933(12) Uani 1 1 d . . . H19A H 0.4134 0.3617 0.8441 0.112 Uiso 1 1 calc R . . H19B H 0.4970 0.5157 0.8226 0.112 Uiso 1 1 calc R . . C20 C 0.2150(7) 0.5232(6) 0.8711(3) 0.1218(16) Uani 1 1 d . . . H20A H 0.1880 0.6089 0.8332 0.183 Uiso 1 1 calc R . . H20B H 0.2206 0.5479 0.9420 0.183 Uiso 1 1 calc R . . H20C H 0.1184 0.4557 0.8755 0.183 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0732(12) 0.0718(12) 0.1018(15) 0.0083(10) -0.0089(11) 0.0121(9) F2 0.1055(17) 0.0617(14) 0.235(3) -0.0388(17) -0.0039(18) -0.0031(12) F3 0.201(3) 0.161(3) 0.193(3) -0.139(3) -0.011(2) -0.011(2) F4 0.223(3) 0.211(4) 0.0704(16) -0.0649(19) -0.0202(18) -0.004(3) F5 0.167(2) 0.1039(18) 0.0638(12) 0.0002(11) -0.0182(13) 0.0072(16) N1 0.0545(12) 0.0563(13) 0.0507(12) -0.0157(10) -0.0141(10) 0.0114(10) N2 0.0509(12) 0.0483(12) 0.0495(12) -0.0067(9) -0.0140(10) 0.0119(9) C1 0.0453(14) 0.0609(18) 0.0583(16) -0.0205(13) -0.0113(12) 0.0084(12) C2 0.0442(15) 0.0605(19) 0.082(2) -0.0160(16) -0.0081(14) 0.0062(13) C3 0.062(2) 0.060(2) 0.145(4) -0.037(2) -0.005(2) -0.0026(16) C4 0.102(3) 0.110(4) 0.122(4) -0.076(3) -0.006(3) -0.009(3) C5 0.111(3) 0.131(4) 0.072(2) -0.052(3) -0.014(2) 0.000(3) C6 0.085(2) 0.086(2) 0.0598(19) -0.0249(18) -0.0129(17) 0.0020(18) C7 0.0437(13) 0.0423(13) 0.0459(13) -0.0054(11) -0.0050(11) 0.0023(10) C8 0.0436(13) 0.0436(13) 0.0466(13) -0.0070(11) -0.0083(11) 0.0043(10) C9 0.0441(13) 0.0436(13) 0.0480(13) -0.0064(11) -0.0107(11) 0.0062(11) C10 0.0411(12) 0.0393(13) 0.0528(14) -0.0030(11) -0.0062(11) 0.0023(10) C11 0.0418(13) 0.0389(13) 0.0521(14) -0.0047(11) -0.0061(11) 0.0002(10) C12 0.0453(14) 0.0498(14) 0.0562(15) -0.0092(12) -0.0048(12) 0.0032(11) C13 0.0422(14) 0.0576(17) 0.0748(19) -0.0150(14) -0.0009(13) 0.0074(12) C14 0.0446(14) 0.0584(17) 0.0758(19) -0.0053(14) -0.0139(14) 0.0100(12) C15 0.0479(14) 0.0504(15) 0.0648(16) -0.0029(13) -0.0139(13) 0.0064(12) C16 0.0524(14) 0.0508(14) 0.0454(13) -0.0094(11) -0.0121(12) 0.0074(11) C17 0.0549(15) 0.0488(15) 0.0518(14) 0.0016(11) -0.0133(12) 0.0041(12) C18 0.0628(17) 0.0610(18) 0.0739(19) -0.0071(15) -0.0222(15) 0.0005(14) C19 0.100(3) 0.108(3) 0.081(2) -0.023(2) -0.041(2) 0.006(2) C20 0.159(4) 0.112(3) 0.089(3) -0.030(3) -0.020(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.350(4) . ? F2 C3 1.342(5) . ? F3 C4 1.335(4) . ? F4 C5 1.356(5) . ? F5 C6 1.320(4) . ? N1 C7 1.297(3) . ? N1 C1 1.390(3) . ? N2 C10 1.387(3) . ? N2 C9 1.395(3) . ? N2 C17 1.468(3) . ? C1 C2 1.376(4) . ? C1 C6 1.398(4) . ? C2 C3 1.377(5) . ? C3 C4 1.373(7) . ? C4 C5 1.343(7) . ? C5 C6 1.373(5) . ? C7 C11 1.457(3) . ? C7 C8 1.468(3) . ? C8 C16 1.382(3) . ? C8 C9 1.406(3) . ? C9 C16 1.393(3) 2_566 ? C10 C15 1.400(3) . ? C10 C11 1.417(3) . ? C11 C12 1.404(3) . ? C12 C13 1.369(4) . ? C12 H12 0.9300 . ? C13 C14 1.382(4) . ? C13 H13 0.9300 . ? C14 C15 1.370(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C9 1.393(3) 2_566 ? C16 H16 0.9300 . ? C17 C18 1.507(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.521(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.480(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 _geom_angle_publ_flag C7 N1 C1 126.0(2) . . ? C10 N2 C9 119.7(2) . . ? C10 N2 C17 121.1(2) . . ? C9 N2 C17 119.0(2) . . ? C2 C1 N1 124.2(3) . . ? C2 C1 C6 115.9(3) . . ? N1 C1 C6 119.1(3) . . ? F1 C2 C1 119.1(3) . . ? F1 C2 C3 118.6(3) . . ? C1 C2 C3 122.4(3) . . ? F2 C3 C4 121.1(4) . . ? F2 C3 C2 119.0(4) . . ? C4 C3 C2 119.9(4) . . ? F3 C4 C5 120.8(5) . . ? F3 C4 C3 120.0(5) . . ? C5 C4 C3 119.2(3) . . ? C4 C5 F4 119.5(4) . . ? C4 C5 C6 121.3(4) . . ? F4 C5 C6 119.2(5) . . ? F5 C6 C5 119.3(4) . . ? F5 C6 C1 119.4(3) . . ? C5 C6 C1 121.3(4) . . ? N1 C7 C11 128.7(2) . . ? N1 C7 C8 116.0(2) . . ? C11 C7 C8 115.2(2) . . ? C16 C8 C9 120.2(2) . . ? C16 C8 C7 119.9(2) . . ? C9 C8 C7 119.8(2) . . ? C16 C9 N2 121.7(2) 2_566 . ? C16 C9 C8 117.9(2) 2_566 . ? N2 C9 C8 120.4(2) . . ? N2 C10 C15 120.3(2) . . ? N2 C10 C11 120.8(2) . . ? C15 C10 C11 118.9(2) . . ? C12 C11 C10 118.5(2) . . ? C12 C11 C7 122.0(2) . . ? C10 C11 C7 119.4(2) . . ? C13 C12 C11 121.4(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 119.6(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 121.0(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 120.6(3) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C8 C16 C9 121.9(2) . 2_566 ? C8 C16 H16 119.1 . . ? C9 C16 H16 119.1 2_566 . ? N2 C17 C18 114.3(2) . . ? N2 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? N2 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 112.8(3) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 112.0(3) . . ? 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_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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 C2 61.2(4) . . . . ? C7 N1 C1 C6 -129.1(3) . . . . ? N1 C1 C2 F1 -9.1(4) . . . . ? C6 C1 C2 F1 -179.1(3) . . . . ? N1 C1 C2 C3 170.2(3) . . . . ? C6 C1 C2 C3 0.2(4) . . . . ? F1 C2 C3 F2 -0.3(5) . . . . ? C1 C2 C3 F2 -179.6(3) . . . . ? F1 C2 C3 C4 -179.9(3) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? F2 C3 C4 F3 0.1(6) . . . . ? C2 C3 C4 F3 179.7(3) . . . . ? F2 C3 C4 C5 179.6(4) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? F3 C4 C5 F4 0.3(7) . . . . ? C3 C4 C5 F4 -179.2(4) . . . . ? F3 C4 C5 C6 179.4(4) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C4 C5 C6 F5 -179.9(4) . . . . ? F4 C5 C6 F5 -0.7(6) . . . . ? C4 C5 C6 C1 1.1(6) . . . . ? F4 C5 C6 C1 -179.8(3) . . . . ? C2 C1 C6 F5 179.8(3) . . . . ? N1 C1 C6 F5 9.3(4) . . . . ? C2 C1 C6 C5 -1.1(5) . . . . ? N1 C1 C6 C5 -171.7(3) . . . . ? C1 N1 C7 C11 12.0(4) . . . . ? C1 N1 C7 C8 -170.6(3) . . . . ? N1 C7 C8 C16 -14.0(4) . . . . ? C11 C7 C8 C16 163.8(2) . . . . ? N1 C7 C8 C9 162.5(2) . . . . ? C11 C7 C8 C9 -19.8(3) . . . . ? C10 N2 C9 C16 -164.9(2) . . . 2_566 ? C17 N2 C9 C16 10.3(4) . . . 2_566 ? C10 N2 C9 C8 14.5(4) . . . . ? C17 N2 C9 C8 -170.2(2) . . . . ? C16 C8 C9 C16 -0.3(4) . . . 2_566 ? C7 C8 C9 C16 -176.8(2) . . . 2_566 ? C16 C8 C9 N2 -179.8(2) . . . . ? C7 C8 C9 N2 3.7(4) . . . . ? C9 N2 C10 C15 163.3(2) . . . . ? C17 N2 C10 C15 -11.8(4) . . . . ? C9 N2 C10 C11 -15.7(3) . . . . ? C17 N2 C10 C11 169.2(2) . . . . ? N2 C10 C11 C12 175.3(2) . . . . ? C15 C10 C11 C12 -3.7(4) . . . . ? N2 C10 C11 C7 -1.5(4) . . . . ? C15 C10 C11 C7 179.5(2) . . . . ? N1 C7 C11 C12 19.4(4) . . . . ? C8 C7 C11 C12 -158.1(2) . . . . ? N1 C7 C11 C10 -164.0(3) . . . . ? C8 C7 C11 C10 18.6(3) . . . . ? C10 C11 C12 C13 2.2(4) . . . . ? C7 C11 C12 C13 178.9(2) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C15 -1.8(4) . . . . ? C13 C14 C15 C10 0.2(4) . . . . ? N2 C10 C15 C14 -176.4(2) . . . . ? C11 C10 C15 C14 2.6(4) . . . . ? C9 C8 C16 C9 0.3(4) . . . 2_566 ? C7 C8 C16 C9 176.8(2) . . . 2_566 ? C10 N2 C17 C18 89.2(3) . . . . ? C9 N2 C17 C18 -86.0(3) . . . . ? N2 C17 C18 C19 170.2(2) . . . . ? C17 C18 C19 C20 -73.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.616 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 923160' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Bis(3,5-dimethylphenyl)-N,N'-di(n-butyl)-2,9- difluoroquinacridonediimine ; _chemical_name_common ; N,N-Bis(3,5-dimethylphenyl)-N,N'-di(n-butyl)-2,9- difluoroquinacridonediimine ; _chemical_melting_point ? _chemical_formula_moiety 'C44 H44 F2 N4' _chemical_formula_sum 'C44 H44 F2 N4' _chemical_formula_weight 666.83 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.453(3) _cell_length_b 7.2220(14) _cell_length_c 31.554(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.38(3) _cell_angle_gamma 90.00 _cell_volume 3514.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13280 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3092 _reflns_number_gt 1789 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3092 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1218 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1620 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.14887(17) 0.4439(4) 0.02270(10) 0.0426(8) Uani 1 1 d . . . C2 C 0.11627(18) 0.4807(4) -0.02289(10) 0.0448(8) Uani 1 1 d . . . H2 H 0.0556 0.4787 -0.0390 0.054 Uiso 1 1 calc R . . C3 C 0.17317(17) 0.5202(4) -0.04467(9) 0.0420(8) Uani 1 1 d . . . H3 H 0.1514 0.5461 -0.0762 0.050 Uiso 1 1 calc R . . C4 C 0.26319(16) 0.5233(4) -0.02123(8) 0.0346(7) Uani 1 1 d . . . C5 C 0.29395(15) 0.4845(4) 0.02521(8) 0.0313(6) Uani 1 1 d . . . C6 C 0.23490(17) 0.4443(4) 0.04692(9) 0.0374(7) Uani 1 1 d . . . H6 H 0.2550 0.4175 0.0784 0.045 Uiso 1 1 calc R . . C7 C 0.28711(17) 0.6322(4) -0.09047(8) 0.0414(7) Uani 1 1 d . . . H7A H 0.3316 0.7111 -0.0960 0.050 Uiso 1 1 calc R . . H7B H 0.2356 0.7105 -0.0944 0.050 Uiso 1 1 calc R . . C8 C 0.2620(2) 0.4794(5) -0.12557(9) 0.0538(9) Uani 1 1 d . . . H8A H 0.2237 0.3903 -0.1178 0.065 Uiso 1 1 calc R . . H8B H 0.3149 0.4120 -0.1248 0.065 Uiso 1 1 calc R . . C9 C 0.2156(2) 0.5521(6) -0.17335(10) 0.0677(11) Uani 1 1 d . . . H9A H 0.2473 0.6617 -0.1783 0.081 Uiso 1 1 calc R . . H9B H 0.2177 0.4558 -0.1953 0.081 Uiso 1 1 calc R . . C10 C 0.1245(2) 0.6040(8) -0.18269(12) 0.0974(16) Uani 1 1 d . . . H10A H 0.0943 0.5021 -0.1739 0.146 Uiso 1 1 calc R . . H10B H 0.0965 0.6293 -0.2150 0.146 Uiso 1 1 calc R . . H10C H 0.1221 0.7151 -0.1653 0.146 Uiso 1 1 calc R . . C11 C 0.41012(15) 0.5352(4) -0.02157(8) 0.0317(7) Uani 1 1 d . . . C12 C 0.46671(15) 0.5370(4) -0.04559(8) 0.0332(7) Uani 1 1 d . . . H12 H 0.4442 0.5649 -0.0770 0.040 Uiso 1 1 calc R . . C13 C 0.44501(16) 0.5002(4) 0.02558(8) 0.0310(6) Uani 1 1 d . . . C14 C 0.38659(16) 0.5005(4) 0.05219(8) 0.0349(7) Uani 1 1 d . . . C15 C 0.48402(17) 0.5616(5) 0.12867(8) 0.0407(8) Uani 1 1 d . . . C16 C 0.52380(17) 0.7297(5) 0.12769(9) 0.0460(8) Uani 1 1 d . . . H16 H 0.5035 0.8036 0.1012 0.055 Uiso 1 1 calc R . . C17 C 0.59292(19) 0.7929(5) 0.16472(10) 0.0541(9) Uani 1 1 d . . . C18 C 0.6344(3) 0.9775(6) 0.16234(13) 0.0851(13) Uani 1 1 d . . . H18A H 0.6628 1.0258 0.1930 0.128 Uiso 1 1 calc R . . H18B H 0.5897 1.0649 0.1448 0.128 Uiso 1 1 calc R . . H18C H 0.6775 0.9616 0.1477 0.128 Uiso 1 1 calc R . . C19 C 0.6211(2) 0.6826(6) 0.20273(10) 0.0604(10) Uani 1 1 d . . . H19 H 0.6678 0.7246 0.2283 0.072 Uiso 1 1 calc R . . C20 C 0.5839(2) 0.5134(6) 0.20483(9) 0.0581(10) Uani 1 1 d . . . C21 C 0.51477(19) 0.4542(5) 0.16761(9) 0.0517(9) Uani 1 1 d . . . H21 H 0.4880 0.3386 0.1687 0.062 Uiso 1 1 calc R . . C22 C 0.6171(3) 0.3934(7) 0.24706(11) 0.0927(15) Uani 1 1 d . . . H22A H 0.6790 0.3684 0.2542 0.139 Uiso 1 1 calc R . . H22B H 0.5851 0.2762 0.2417 0.139 Uiso 1 1 calc R . . H22C H 0.6085 0.4584 0.2725 0.139 Uiso 1 1 calc R . . F1 F 0.09193(10) 0.4066(3) 0.04457(6) 0.0614(6) Uani 1 1 d . . . N1 N 0.40515(14) 0.5101(4) 0.09526(7) 0.0438(7) Uani 1 1 d . . . N2 N 0.32123(13) 0.5650(3) -0.04323(6) 0.0360(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0336(16) 0.043(2) 0.0624(19) 0.0008(14) 0.0309(14) -0.0010(13) C2 0.0273(15) 0.048(2) 0.0581(19) 0.0004(15) 0.0142(13) 0.0043(14) C3 0.0304(15) 0.048(2) 0.0467(16) 0.0005(14) 0.0127(12) 0.0044(13) C4 0.0294(15) 0.0339(19) 0.0428(16) -0.0014(12) 0.0152(12) 0.0027(12) C5 0.0258(14) 0.0299(18) 0.0406(15) -0.0029(12) 0.0147(11) 0.0020(12) C6 0.0356(16) 0.0348(19) 0.0460(16) 0.0013(13) 0.0193(12) 0.0032(13) C7 0.0340(15) 0.049(2) 0.0418(16) 0.0053(14) 0.0144(12) 0.0049(14) C8 0.0432(17) 0.064(3) 0.0501(18) -0.0052(16) 0.0102(14) 0.0065(16) C9 0.054(2) 0.101(4) 0.0447(19) 0.0012(18) 0.0130(15) 0.003(2) C10 0.068(3) 0.153(5) 0.066(2) 0.020(3) 0.017(2) 0.035(3) C11 0.0252(14) 0.0355(19) 0.0341(15) -0.0014(11) 0.0097(11) 0.0016(12) C12 0.0269(14) 0.0395(19) 0.0333(14) -0.0023(12) 0.0105(11) -0.0013(12) C13 0.0289(14) 0.0307(17) 0.0353(14) -0.0014(12) 0.0137(11) -0.0003(12) C14 0.0314(15) 0.037(2) 0.0389(16) -0.0009(12) 0.0152(11) 0.0013(12) C15 0.0311(15) 0.061(2) 0.0341(15) -0.0023(13) 0.0162(12) 0.0032(15) C16 0.0382(16) 0.061(2) 0.0407(16) -0.0021(14) 0.0167(13) 0.0039(16) C17 0.0446(18) 0.065(3) 0.054(2) -0.0178(17) 0.0190(15) -0.0007(17) C18 0.078(3) 0.079(4) 0.092(3) -0.020(2) 0.022(2) -0.023(2) C19 0.0424(18) 0.095(3) 0.0389(18) -0.0146(18) 0.0088(14) 0.001(2) C20 0.0435(19) 0.091(3) 0.0381(17) 0.0040(18) 0.0120(14) 0.0065(19) C21 0.0437(18) 0.069(3) 0.0459(18) 0.0034(16) 0.0203(14) 0.0002(16) C22 0.074(3) 0.139(5) 0.054(2) 0.029(2) 0.0083(18) 0.012(3) F1 0.0377(10) 0.0815(16) 0.0769(12) 0.0116(10) 0.0349(9) -0.0007(9) N1 0.0319(13) 0.066(2) 0.0361(13) 0.0004(12) 0.0154(10) -0.0042(12) N2 0.0252(12) 0.0504(17) 0.0330(12) 0.0049(10) 0.0110(9) 0.0046(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.354(4) . ? C1 F1 1.370(3) . ? C1 C2 1.375(4) . ? C2 C3 1.370(4) . ? C2 H2 0.9500 . ? C3 C4 1.407(4) . ? C3 H3 0.9500 . ? C4 N2 1.395(3) . ? C4 C5 1.402(4) . ? C5 C6 1.400(3) . ? C5 C14 1.469(3) . ? C6 H6 0.9500 . ? C7 N2 1.480(3) . ? C7 C8 1.515(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.527(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.471(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.390(3) . ? C11 N2 1.399(3) . ? C11 C13 1.419(4) . ? C12 C13 1.394(3) 5_665 ? C12 H12 0.9500 . ? C13 C12 1.394(3) 5_665 ? C13 C14 1.480(3) . ? C14 N1 1.287(3) . ? C15 C16 1.385(4) . ? C15 C21 1.391(4) . ? C15 N1 1.407(3) . ? C16 C17 1.393(4) . ? C16 H16 0.9500 . ? C17 C19 1.378(5) . ? C17 C18 1.512(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.379(5) . ? C19 H19 0.9500 . ? C20 C21 1.387(4) . ? C20 C22 1.522(5) . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 _geom_angle_publ_flag C6 C1 F1 118.7(3) . . ? C6 C1 C2 122.7(2) . . ? F1 C1 C2 118.6(2) . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? N2 C4 C5 120.2(2) . . ? N2 C4 C3 121.3(2) . . ? C5 C4 C3 118.5(2) . . ? C6 C5 C4 119.6(2) . . ? C6 C5 C14 119.3(2) . . ? C4 C5 C14 120.9(2) . . ? C1 C6 C5 119.4(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? N2 C7 C8 114.1(3) . . ? N2 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N2 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 112.7(3) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 114.2(3) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N2 121.1(2) . . ? C12 C11 C13 118.0(2) . . ? N2 C11 C13 120.8(2) . . ? C11 C12 C13 122.8(2) . 5_665 ? C11 C12 H12 118.6 . . ? C13 C12 H12 118.6 5_665 . ? C12 C13 C11 119.1(2) 5_665 . ? C12 C13 C14 121.6(2) 5_665 . ? C11 C13 C14 119.3(2) . . ? N1 C14 C5 115.7(2) . . ? N1 C14 C13 129.6(2) . . ? C5 C14 C13 114.8(2) . . ? C16 C15 C21 118.6(3) . . ? C16 C15 N1 122.3(3) . . ? C21 C15 N1 118.1(3) . . ? C15 C16 C17 121.5(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C19 C17 C16 118.0(3) . . ? C19 C17 C18 122.1(3) . . ? C16 C17 C18 119.9(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C17 122.2(3) . . ? C20 C19 H19 118.9 . . ? C17 C19 H19 118.9 . . ? C19 C20 C21 118.6(3) . . ? C19 C20 C22 121.1(3) . . ? C21 C20 C22 120.3(4) . . ? C20 C21 C15 121.0(3) . . ? C20 C21 H21 119.5 . . ? C15 C21 H21 119.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 N1 C15 128.5(2) . . ? C4 N2 C11 120.3(2) . . ? C4 N2 C7 119.1(2) . . ? C11 N2 C7 120.5(2) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.3(5) . . . . ? F1 C1 C2 C3 179.2(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 N2 -179.5(3) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? N2 C4 C5 C6 179.5(3) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? N2 C4 C5 C14 4.6(4) . . . . ? C3 C4 C5 C14 -175.0(3) . . . . ? F1 C1 C6 C5 -179.2(3) . . . . ? C2 C1 C6 C5 0.4(5) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C14 C5 C6 C1 174.8(3) . . . . ? N2 C7 C8 C9 172.0(2) . . . . ? C7 C8 C9 C10 -76.4(4) . . . . ? N2 C11 C12 C13 -177.1(3) . . . 5_665 ? C13 C11 C12 C13 2.3(5) . . . 5_665 ? C12 C11 C13 C12 -2.2(4) . . . 5_665 ? N2 C11 C13 C12 177.2(3) . . . 5_665 ? C12 C11 C13 C14 179.0(3) . . . . ? N2 C11 C13 C14 -1.7(4) . . . . ? C6 C5 C14 N1 -12.5(4) . . . . ? C4 C5 C14 N1 162.4(3) . . . . ? C6 C5 C14 C13 166.6(2) . . . . ? C4 C5 C14 C13 -18.5(4) . . . . ? C12 C13 C14 N1 17.0(5) 5_665 . . . ? C11 C13 C14 N1 -164.2(3) . . . . ? C12 C13 C14 C5 -162.0(3) 5_665 . . . ? C11 C13 C14 C5 16.9(4) . . . . ? C21 C15 C16 C17 -0.4(4) . . . . ? N1 C15 C16 C17 168.4(2) . . . . ? C15 C16 C17 C19 0.1(4) . . . . ? C15 C16 C17 C18 -179.8(3) . . . . ? C16 C17 C19 C20 0.7(5) . . . . ? C18 C17 C19 C20 -179.4(3) . . . . ? C17 C19 C20 C21 -1.1(5) . . . . ? C17 C19 C20 C22 179.2(3) . . . . ? C19 C20 C21 C15 0.8(5) . . . . ? C22 C20 C21 C15 -179.6(3) . . . . ? C16 C15 C21 C20 0.0(4) . . . . ? N1 C15 C21 C20 -169.3(3) . . . . ? C5 C14 N1 C15 -166.4(3) . . . . ? C13 C14 N1 C15 14.7(5) . . . . ? C16 C15 N1 C14 56.1(5) . . . . ? C21 C15 N1 C14 -135.1(3) . . . . ? C5 C4 N2 C11 12.0(4) . . . . ? C3 C4 N2 C11 -168.5(3) . . . . ? C5 C4 N2 C7 -171.1(3) . . . . ? C3 C4 N2 C7 8.5(4) . . . . ? C12 C11 N2 C4 165.9(3) . . . . ? C13 C11 N2 C4 -13.4(4) . . . . ? C12 C11 N2 C7 -11.0(4) . . . . ? C13 C11 N2 C7 169.7(3) . . . . ? C8 C7 N2 C4 -86.2(3) . . . . ? C8 C7 N2 C11 90.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.202 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 923161' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-Bis(4-cyanophenyl)-N,N'-di(n-octyl) quinacridonediimine ; _chemical_name_common ; N,N-Bis(4-cyanophenyl)-N,N'-di(n-octyl) quinacridonediimine ; _chemical_melting_point ? _chemical_formula_moiety 'C50 H52 N6' _chemical_formula_sum 'C50 H52 N6' _chemical_formula_weight 736.98 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8472(18) _cell_length_b 9.2195(18) _cell_length_c 14.044(3) _cell_angle_alpha 84.46(3) _cell_angle_beta 76.26(3) _cell_angle_gamma 64.35(3) _cell_volume 1003.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 263(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 394 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 263(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9921 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.1078 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4544 _reflns_number_gt 2000 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4544 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1607 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1580 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.7595(3) 0.2506(3) 0.01199(18) 0.0395(6) Uani 1 1 d . . . C2 C 0.7326(4) 0.1129(3) 0.00722(19) 0.0517(8) Uani 1 1 d . . . H2 H 0.8091 0.0313 -0.0398 0.062 Uiso 1 1 calc R . . C3 C 0.5972(4) 0.0944(4) 0.0695(2) 0.0594(9) Uani 1 1 d . . . H3 H 0.5808 -0.0001 0.0666 0.071 Uiso 1 1 calc R . . C4 C 0.4850(4) 0.2148(4) 0.1367(2) 0.0635(9) Uani 1 1 d . . . H4 H 0.3894 0.2033 0.1787 0.076 Uiso 1 1 calc R . . C5 C 0.5086(3) 0.3498(4) 0.1441(2) 0.0543(8) Uani 1 1 d . . . H5 H 0.4302 0.4308 0.1910 0.065 Uiso 1 1 calc R . . C6 C 0.6500(3) 0.3690(3) 0.08167(18) 0.0402(6) Uani 1 1 d . . . C7 C 0.8371(3) 0.5035(3) 0.04408(17) 0.0374(6) Uani 1 1 d . . . C8 C 0.9491(3) 0.3913(3) -0.03017(17) 0.0356(6) Uani 1 1 d . . . C9 C 0.8954(3) 0.2758(3) -0.06132(18) 0.0403(6) Uani 1 1 d . . . C10 C 0.8898(3) 0.6118(3) 0.07231(17) 0.0386(6) Uani 1 1 d . . . H10 H 0.8142 0.6899 0.1215 0.046 Uiso 1 1 calc R . . C11 C 1.0483(3) 0.2236(3) -0.22974(19) 0.0447(7) Uani 1 1 d . . . C12 C 1.1958(4) 0.0977(4) -0.2770(2) 0.0527(7) Uani 1 1 d . . . H12 H 1.2421 -0.0010 -0.2435 0.063 Uiso 1 1 calc R . . C13 C 1.2767(4) 0.1131(4) -0.3717(2) 0.0554(8) Uani 1 1 d . . . H13 H 1.3783 0.0258 -0.4029 0.066 Uiso 1 1 calc R . . C14 C 1.2089(4) 0.2573(4) -0.4217(2) 0.0503(7) Uani 1 1 d . . . C15 C 1.0648(3) 0.3844(4) -0.3740(2) 0.0535(8) Uani 1 1 d . . . H15 H 1.0195 0.4837 -0.4071 0.064 Uiso 1 1 calc R . . C16 C 0.9856(3) 0.3690(3) -0.27906(19) 0.0491(7) Uani 1 1 d . . . H16 H 0.8874 0.4582 -0.2469 0.059 Uiso 1 1 calc R . . C17 C 1.2852(4) 0.2702(4) -0.5225(2) 0.0625(9) Uani 1 1 d . . . C18 C 0.5462(3) 0.6404(3) 0.15110(18) 0.0423(6) Uani 1 1 d . . . H18A H 0.4319 0.6552 0.1436 0.051 Uiso 1 1 calc R . . H18B H 0.5604 0.7393 0.1272 0.051 Uiso 1 1 calc R . . C19 C 0.5490(3) 0.6222(4) 0.25931(19) 0.0482(7) Uani 1 1 d . . . H19A H 0.5665 0.5112 0.2796 0.058 Uiso 1 1 calc R . . H19B H 0.6473 0.6387 0.2697 0.058 Uiso 1 1 calc R . . C20 C 0.3849(3) 0.7401(4) 0.3232(2) 0.0575(8) Uani 1 1 d . . . H20A H 0.3825 0.8489 0.3152 0.069 Uiso 1 1 calc R . . H20B H 0.2853 0.7439 0.3008 0.069 Uiso 1 1 calc R . . C21 C 0.3673(4) 0.6963(4) 0.4308(2) 0.0587(8) Uani 1 1 d . . . H21A H 0.3845 0.5827 0.4372 0.070 Uiso 1 1 calc R . . H21B H 0.4605 0.7043 0.4543 0.070 Uiso 1 1 calc R . . C22 C 0.1992(3) 0.7976(4) 0.4964(2) 0.0571(8) Uani 1 1 d . . . H22A H 0.1053 0.7928 0.4719 0.069 Uiso 1 1 calc R . . H22B H 0.1836 0.9108 0.4922 0.069 Uiso 1 1 calc R . . C23 C 0.1831(3) 0.7474(4) 0.60277(19) 0.0541(7) Uani 1 1 d . . . H23A H 0.2087 0.6316 0.6063 0.065 Uiso 1 1 calc R . . H23B H 0.2709 0.7612 0.6288 0.065 Uiso 1 1 calc R . . C24 C 0.0096(4) 0.8395(4) 0.6675(2) 0.0614(8) Uani 1 1 d . . . H24A H -0.0782 0.8260 0.6415 0.074 Uiso 1 1 calc R . . H24B H -0.0159 0.9554 0.6641 0.074 Uiso 1 1 calc R . . C25 C -0.0061(4) 0.7890(4) 0.7736(2) 0.0724(10) Uani 1 1 d . . . H25A H 0.0114 0.6762 0.7784 0.109 Uiso 1 1 calc R . . H25B H -0.1209 0.8569 0.8112 0.109 Uiso 1 1 calc R . . H25C H 0.0808 0.8010 0.8002 0.109 Uiso 1 1 calc R . . N1 N 0.6779(2) 0.5052(3) 0.08906(15) 0.0409(5) Uani 1 1 d . . . N2 N 0.9514(3) 0.1965(3) -0.14192(16) 0.0494(6) Uani 1 1 d . . . N3 N 1.3430(4) 0.2827(4) -0.6035(2) 0.0877(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0444(15) 0.0478(16) 0.0342(14) 0.0046(13) -0.0153(12) -0.0242(14) C2 0.0690(19) 0.060(2) 0.0402(16) 0.0070(14) -0.0188(14) -0.0384(18) C3 0.078(2) 0.068(2) 0.0537(19) 0.0093(17) -0.0194(17) -0.049(2) C4 0.062(2) 0.091(3) 0.057(2) 0.0078(19) -0.0104(16) -0.054(2) C5 0.0489(17) 0.072(2) 0.0515(18) 0.0004(16) -0.0083(14) -0.0355(18) C6 0.0408(14) 0.0518(17) 0.0347(14) 0.0019(13) -0.0126(12) -0.0240(14) C7 0.0364(14) 0.0450(16) 0.0330(14) 0.0006(12) -0.0104(11) -0.0180(13) C8 0.0354(13) 0.0446(16) 0.0295(13) 0.0006(12) -0.0092(11) -0.0182(13) C9 0.0428(15) 0.0465(17) 0.0366(15) -0.0003(13) -0.0114(12) -0.0221(14) C10 0.0404(14) 0.0437(16) 0.0294(13) -0.0044(12) -0.0051(11) -0.0161(13) C11 0.0483(16) 0.0534(18) 0.0386(15) -0.0128(14) -0.0067(13) -0.0260(16) C12 0.0562(18) 0.0499(19) 0.0475(18) -0.0061(15) -0.0077(15) -0.0189(17) C13 0.0476(17) 0.062(2) 0.0473(18) -0.0173(16) 0.0001(14) -0.0168(17) C14 0.0467(16) 0.068(2) 0.0376(15) -0.0087(15) -0.0053(13) -0.0260(17) C15 0.0494(17) 0.065(2) 0.0455(18) 0.0013(16) -0.0144(14) -0.0222(18) C16 0.0455(16) 0.0518(18) 0.0459(17) -0.0087(14) -0.0059(13) -0.0172(15) C17 0.0523(18) 0.086(3) 0.0464(19) -0.0106(17) -0.0076(15) -0.0260(19) C18 0.0347(14) 0.0492(17) 0.0394(15) -0.0030(13) -0.0065(12) -0.0147(14) C19 0.0399(15) 0.0616(19) 0.0400(15) -0.0059(14) -0.0071(12) -0.0181(15) C20 0.0440(16) 0.066(2) 0.0501(18) -0.0078(16) -0.0077(14) -0.0120(16) C21 0.0485(17) 0.069(2) 0.0486(18) -0.0075(16) -0.0084(14) -0.0152(17) C22 0.0472(17) 0.062(2) 0.0496(18) -0.0030(16) -0.0068(14) -0.0129(16) C23 0.0492(17) 0.062(2) 0.0461(17) -0.0022(15) -0.0076(14) -0.0195(16) C24 0.0559(19) 0.075(2) 0.0518(19) -0.0009(17) -0.0108(15) -0.0261(19) C25 0.077(2) 0.089(3) 0.053(2) -0.0040(19) -0.0042(17) -0.041(2) N1 0.0350(11) 0.0513(14) 0.0387(12) -0.0068(11) -0.0050(10) -0.0207(12) N2 0.0578(15) 0.0568(16) 0.0402(13) -0.0103(12) -0.0029(11) -0.0321(14) N3 0.080(2) 0.125(3) 0.0486(18) -0.0052(18) -0.0034(15) -0.039(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.388(4) . ? C1 C2 1.399(3) . ? C1 C9 1.473(3) . ? C2 C3 1.371(4) . ? C2 H2 0.9500 . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.365(4) . ? C4 H4 0.9500 . ? C5 C6 1.416(3) . ? C5 H5 0.9500 . ? C6 N1 1.398(3) . ? C7 N1 1.394(3) . ? C7 C10 1.393(3) . ? C7 C8 1.403(3) . ? C8 C10 1.397(3) 2_765 ? C8 C9 1.475(3) . ? C9 N2 1.281(3) . ? C10 C8 1.397(3) 2_765 ? C10 H10 0.9500 . ? C11 C12 1.384(4) . ? C11 C16 1.394(4) . ? C11 N2 1.393(3) . ? C12 C13 1.379(4) . ? C12 H12 0.9500 . ? C13 C14 1.396(4) . ? C13 H13 0.9500 . ? C14 C15 1.378(4) . ? C14 C17 1.434(4) . ? C15 C16 1.377(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N3 1.149(4) . ? C18 N1 1.463(3) . ? C18 C19 1.518(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.516(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.514(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.499(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.513(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.504(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.511(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 _geom_angle_publ_flag C6 C1 C2 119.9(2) . . ? C6 C1 C9 119.9(2) . . ? C2 C1 C9 120.1(3) . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 N1 120.5(2) . . ? C1 C6 C5 118.7(2) . . ? N1 C6 C5 120.8(3) . . ? N1 C7 C10 120.9(2) . . ? N1 C7 C8 120.8(2) . . ? C10 C7 C8 118.3(2) . . ? C10 C8 C7 120.0(2) 2_765 . ? C10 C8 C9 120.9(2) 2_765 . ? C7 C8 C9 119.1(2) . . ? N2 C9 C1 117.2(2) . . ? N2 C9 C8 128.8(2) . . ? C1 C9 C8 114.0(2) . . ? C7 C10 C8 121.7(2) . 2_765 ? C7 C10 H10 119.1 . . ? C8 C10 H10 119.1 2_765 . ? C12 C11 C16 118.5(2) . . ? C12 C11 N2 119.9(3) . . ? C16 C11 N2 120.9(3) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.8(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.2(3) . . ? C15 C14 C17 120.7(3) . . ? C13 C14 C17 120.1(3) . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 120.6(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? N3 C17 C14 178.6(4) . . ? N1 C18 C19 115.0(2) . . ? N1 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? N1 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C20 C19 C18 112.8(2) . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19B 109.0 . . ? C18 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C19 112.9(2) . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C20 115.4(2) . . ? C22 C21 H21A 108.4 . . ? C20 C21 H21A 108.4 . . ? C22 C21 H21B 108.4 . . ? C20 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? C21 C22 C23 114.2(2) . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22B 108.7 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C22 114.5(2) . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C23 C24 C25 114.4(3) . . ? C23 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? C23 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C7 N1 C6 119.1(2) . . ? C7 N1 C18 121.1(2) . . ? C6 N1 C18 119.55(19) . . ? C9 N2 C11 128.2(2) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.2(4) . . . . ? C9 C1 C2 C3 -174.3(2) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C2 C3 C4 C5 -1.7(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C2 C1 C6 N1 178.3(2) . . . . ? C9 C1 C6 N1 -6.3(3) . . . . ? C2 C1 C6 C5 -2.5(3) . . . . ? C9 C1 C6 C5 172.9(2) . . . . ? C4 C5 C6 C1 1.8(4) . . . . ? C4 C5 C6 N1 -179.0(2) . . . . ? N1 C7 C8 C10 -178.0(2) . . . 2_765 ? C10 C7 C8 C10 1.3(4) . . . 2_765 ? N1 C7 C8 C9 0.8(3) . . . . ? C10 C7 C8 C9 -179.8(2) . . . . ? C6 C1 C9 N2 -156.0(2) . . . . ? C2 C1 C9 N2 19.5(4) . . . . ? C6 C1 C9 C8 24.3(3) . . . . ? C2 C1 C9 C8 -160.3(2) . . . . ? C10 C8 C9 N2 -22.3(4) 2_765 . . . ? C7 C8 C9 N2 158.8(3) . . . . ? C10 C8 C9 C1 157.4(2) 2_765 . . . ? C7 C8 C9 C1 -21.5(3) . . . . ? N1 C7 C10 C8 178.0(2) . . . 2_765 ? C8 C7 C10 C8 -1.3(4) . . . 2_765 ? C16 C11 C12 C13 -2.0(4) . . . . ? N2 C11 C12 C13 168.1(2) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C15 2.2(4) . . . . ? C12 C13 C14 C17 -175.5(2) . . . . ? C13 C14 C15 C16 -1.5(4) . . . . ? C17 C14 C15 C16 176.2(2) . . . . ? C14 C15 C16 C11 -1.0(4) . . . . ? C12 C11 C16 C15 2.7(4) . . . . ? N2 C11 C16 C15 -167.2(2) . . . . ? C15 C14 C17 N3 -30(15) . . . . ? C13 C14 C17 N3 148(15) . . . . ? N1 C18 C19 C20 -164.4(2) . . . . ? C18 C19 C20 C21 165.4(2) . . . . ? C19 C20 C21 C22 -173.5(2) . . . . ? C20 C21 C22 C23 178.0(2) . . . . ? C21 C22 C23 C24 -175.2(2) . . . . ? C22 C23 C24 C25 179.9(3) . . . . ? C10 C7 N1 C6 -160.6(2) . . . . ? C8 C7 N1 C6 18.7(3) . . . . ? C10 C7 N1 C18 13.6(3) . . . . ? C8 C7 N1 C18 -167.1(2) . . . . ? C1 C6 N1 C7 -15.9(3) . . . . ? C5 C6 N1 C7 164.9(2) . . . . ? C1 C6 N1 C18 169.8(2) . . . . ? C5 C6 N1 C18 -9.4(3) . . . . ? C19 C18 N1 C7 -91.8(3) . . . . ? C19 C18 N1 C6 82.4(3) . . . . ? C1 C9 N2 C11 164.2(3) . . . . ? C8 C9 N2 C11 -16.0(5) . . . . ? C12 C11 N2 C9 130.3(3) . . . . ? C16 C11 N2 C9 -59.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.204 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 923162'