Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof Maria Gdaniec' _publ_contact_author_address ; Faculty of Chemistry Adam Mickiewicz University Poznan 60-780 POLAND ; _publ_contact_author_email MAGDAN@AMU.EDU.PL _publ_section_title ; Interplay of Hydrogen Bonding and Aromatic Ring Interactions in Supramolecular Complexes of Phenazine with N,N'-Bis(2-pyridyl) aryldiamines ; loop_ _publ_author_name 'Maria Gdaniec' 'Igor Bensemann' 'Tadeusz Polonski' data_1-phz _database_code_depnum_ccdc_archive 'CCDC 198837' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,4-diaminobenzene phenazine 1:4 complex ; _chemical_melting_point 171 _chemical_formula_moiety 'C16 H14 N4, 4(C12 H8 N2)' _chemical_formula_sum 'C64 H46 N12' _chemical_formula_weight 983.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8663(9) _cell_length_b 10.7948(9) _cell_length_c 12.5957(9) _cell_angle_alpha 108.446(7) _cell_angle_beta 101.895(7) _cell_angle_gamma 93.506(7) _cell_volume 1233.66(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 11 _cell_measurement_theta_max 28 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 0.637 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <1.5 _diffrn_reflns_number 4348 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 66.59 _reflns_number_total 4339 _reflns_number_gt 3580 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0617P)^2^+0.1403P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap,geom _refine_ls_hydrogen_treatment refu _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0048(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4339 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 N1 N 0.38482(11) -0.12354(11) 0.03664(9) 0.0523(3) Uani 1 1 d . . . C2 C 0.31920(12) -0.16193(11) 0.10549(10) 0.0435(3) Uani 1 1 d . . . C3 C 0.37903(14) -0.23424(13) 0.17367(11) 0.0532(3) Uani 1 1 d . . . H3 H 0.3285 -0.2577 0.2235 0.064(4) Uiso 1 1 d R . . C4 C 0.50900(15) -0.26741(15) 0.16875(13) 0.0641(4) Uani 1 1 d . . . H4 H 0.5513 -0.3165 0.2153 0.079(5) Uiso 1 1 d R . . C5 C 0.57865(15) -0.22870(15) 0.09725(13) 0.0641(4) Uani 1 1 d . . . H5 H 0.6707 -0.2513 0.0941 0.082(5) Uiso 1 1 d R . . C6 C 0.51374(14) -0.15734(14) 0.03530(12) 0.0599(4) Uani 1 1 d . . . H6 H 0.5580 -0.1281 -0.0153 0.067(4) Uiso 1 1 d R . . N7 N 0.18774(10) -0.13035(11) 0.11231(9) 0.0501(3) Uani 1 1 d . . . H7 H 0.1511 -0.1548 0.1636 0.055(4) Uiso 1 1 d R . . C8 C 0.09888(12) -0.06367(11) 0.05413(9) 0.0418(3) Uani 1 1 d . . . C9 C -0.02502(13) -0.03806(12) 0.08815(10) 0.0460(3) Uani 1 1 d . . . H9 H -0.0432 -0.0651 0.1501 0.048(3) Uiso 1 1 d R . . C10 C 0.12269(13) -0.02406(12) -0.03624(10) 0.0457(3) Uani 1 1 d . . . H10 H 0.2087 -0.0378 -0.0598 0.047(3) Uiso 1 1 d R . . N1A N 0.55680(13) 0.41239(11) 0.62061(10) 0.0584(3) Uani 1 1 d . . . C2A C 0.68130(16) 0.48825(13) 0.66580(11) 0.0550(3) Uani 1 1 d . . . C3A C 0.7147(2) 0.57103(16) 0.78302(13) 0.0716(4) Uani 1 1 d . . . H3A H 0.6418 0.5697 0.8228 0.081(5) Uiso 1 1 d R . . C4A C 0.8387(2) 0.65087(17) 0.82878(14) 0.0823(5) Uani 1 1 d . . . H4A H 0.8635 0.7051 0.9086 0.099(6) Uiso 1 1 d R . . C5A C 0.9373(2) 0.65231(16) 0.76230(16) 0.0781(5) Uani 1 1 d . . . H5A H 1.0257 0.7075 0.7974 0.105(7) Uiso 1 1 d R . . C6A C 0.91074(17) 0.57463(15) 0.65086(15) 0.0673(4) Uani 1 1 d . . . H6A H 0.9762 0.5693 0.6033 0.093(6) Uiso 1 1 d R . . C7A C 0.78196(15) 0.49000(13) 0.59884(12) 0.0534(3) Uani 1 1 d . . . N8A N 0.75682(13) 0.41367(11) 0.48785(10) 0.0566(3) Uani 1 1 d . . . C9A C 0.63189(16) 0.33818(12) 0.44287(11) 0.0541(3) Uani 1 1 d . . . C10A C 0.5975(2) 0.25571(15) 0.32499(13) 0.0694(4) Uani 1 1 d . . . H10A H 0.6703 0.2596 0.2855 0.079(5) Uiso 1 1 d R . . C11A C 0.4713(2) 0.17974(16) 0.27872(14) 0.0810(5) Uani 1 1 d . . . H11A H 0.4455 0.1255 0.1989 0.112(7) Uiso 1 1 d R . . C12A C 0.3714(2) 0.18162(16) 0.34396(15) 0.0782(5) Uani 1 1 d . . . H12A H 0.2806 0.1310 0.3082 0.090(6) Uiso 1 1 d R . . C13A C 0.39908(17) 0.25765(15) 0.45563(14) 0.0678(4) Uani 1 1 d . . . H13A H 0.3299 0.2606 0.4997 0.098(6) Uiso 1 1 d R . . C14A C 0.53058(15) 0.33776(13) 0.50928(12) 0.0536(3) Uani 1 1 d . . . N1B N 0.91824(11) 0.22876(10) 0.71159(9) 0.0500(3) Uani 1 1 d . . . C2B C 1.03157(13) 0.32089(12) 0.75471(11) 0.0476(3) Uani 1 1 d . . . C3B C 1.06938(15) 0.39370(14) 0.87422(12) 0.0581(3) Uani 1 1 d . . . H3B H 1.0121 0.3712 0.9202 0.075(5) Uiso 1 1 d R . . C4B C 1.18051(17) 0.48909(15) 0.91823(13) 0.0659(4) Uani 1 1 d . . . H4B H 1.2106 0.5367 0.9994 0.084(5) Uiso 1 1 d R . . C5B C 1.26176(16) 0.51732(15) 0.84644(14) 0.0659(4) Uani 1 1 d . . . H5B H 1.3416 0.5843 0.8784 0.086(5) Uiso 1 1 d R . . C6B C 1.23145(14) 0.44870(14) 0.73208(13) 0.0580(3) Uani 1 1 d . . . H6B H 1.2863 0.4637 0.6815 0.063(4) Uiso 1 1 d R . . C7B C 1.11523(13) 0.34736(12) 0.68221(11) 0.0482(3) Uani 1 1 d . . . N8B N 1.08614(12) 0.27981(11) 0.56897(9) 0.0524(3) Uani 1 1 d . . . C9B C 0.97177(14) 0.18964(12) 0.52583(11) 0.0499(3) Uani 1 1 d . . . C10B C 0.93364(17) 0.11629(15) 0.40591(12) 0.0626(4) Uani 1 1 d . . . H10B H 0.9949 0.1368 0.3619 0.078(5) Uiso 1 1 d R . . C11B C 0.81729(18) 0.02794(16) 0.36103(14) 0.0710(4) Uani 1 1 d . . . H11B H 0.7929 -0.0179 0.2794 0.091(6) Uiso 1 1 d R . . C12B C 0.73085(17) 0.00472(16) 0.43118(14) 0.0694(4) Uani 1 1 d . . . H12B H 0.6491 -0.0600 0.3967 0.089(5) Uiso 1 1 d R . . C13B C 0.76378(15) 0.07005(14) 0.54572(13) 0.0609(4) Uani 1 1 d . . . H13B H 0.7070 0.0573 0.5958 0.075(5) Uiso 1 1 d R . . C14B C 0.88557(14) 0.16480(12) 0.59749(11) 0.0489(3) 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 N1 0.0504(6) 0.0585(6) 0.0568(6) 0.0276(5) 0.0180(5) 0.0096(5) C2 0.0452(6) 0.0423(6) 0.0425(6) 0.0149(5) 0.0089(5) 0.0037(5) C3 0.0535(7) 0.0592(8) 0.0542(7) 0.0279(6) 0.0135(6) 0.0113(6) C4 0.0588(8) 0.0721(9) 0.0683(9) 0.0330(8) 0.0117(7) 0.0206(7) C5 0.0481(8) 0.0730(9) 0.0735(9) 0.0257(8) 0.0152(7) 0.0165(7) C6 0.0519(8) 0.0700(9) 0.0647(8) 0.0268(7) 0.0220(6) 0.0085(6) N7 0.0481(6) 0.0640(6) 0.0537(6) 0.0360(5) 0.0182(5) 0.0137(5) C8 0.0441(6) 0.0434(6) 0.0396(6) 0.0167(5) 0.0100(5) 0.0043(5) C9 0.0504(7) 0.0548(7) 0.0418(6) 0.0248(5) 0.0166(5) 0.0077(5) C10 0.0439(6) 0.0548(7) 0.0458(6) 0.0231(5) 0.0162(5) 0.0089(5) N1A 0.0702(8) 0.0581(7) 0.0531(7) 0.0247(5) 0.0187(5) 0.0083(6) C2A 0.0717(9) 0.0491(7) 0.0483(7) 0.0232(6) 0.0112(6) 0.0119(6) C3A 0.0980(12) 0.0666(9) 0.0494(8) 0.0197(7) 0.0147(8) 0.0141(9) C4A 0.1123(15) 0.0631(10) 0.0544(9) 0.0135(8) -0.0071(9) 0.0110(10) C5A 0.0817(11) 0.0602(9) 0.0810(12) 0.0266(8) -0.0077(9) 0.0015(8) C6A 0.0660(9) 0.0565(8) 0.0782(10) 0.0292(8) 0.0050(8) 0.0055(7) C7A 0.0637(8) 0.0464(7) 0.0548(8) 0.0245(6) 0.0107(6) 0.0127(6) N8A 0.0680(7) 0.0514(6) 0.0566(7) 0.0230(5) 0.0196(6) 0.0108(5) C9A 0.0726(9) 0.0444(7) 0.0501(7) 0.0215(6) 0.0153(6) 0.0109(6) C10A 0.1017(12) 0.0567(8) 0.0522(8) 0.0188(7) 0.0226(8) 0.0113(8) C11A 0.1208(15) 0.0556(9) 0.0535(9) 0.0149(7) 0.0023(9) -0.0023(9) C12A 0.0930(13) 0.0619(9) 0.0707(10) 0.0272(8) -0.0017(9) -0.0104(9) C13A 0.0700(10) 0.0616(9) 0.0733(10) 0.0298(8) 0.0117(8) -0.0007(7) C14A 0.0670(8) 0.0471(7) 0.0520(7) 0.0242(6) 0.0138(6) 0.0085(6) N1B 0.0531(6) 0.0553(6) 0.0504(6) 0.0262(5) 0.0175(5) 0.0084(5) C2B 0.0500(7) 0.0506(7) 0.0498(7) 0.0246(6) 0.0149(5) 0.0124(5) C3B 0.0635(8) 0.0637(8) 0.0510(7) 0.0217(6) 0.0169(6) 0.0127(7) C4B 0.0693(9) 0.0654(9) 0.0561(9) 0.0145(7) 0.0089(7) 0.0116(7) C5B 0.0586(8) 0.0568(8) 0.0750(10) 0.0176(7) 0.0082(7) 0.0039(7) C6B 0.0534(8) 0.0559(8) 0.0708(9) 0.0273(7) 0.0189(7) 0.0067(6) C7B 0.0506(7) 0.0484(7) 0.0535(7) 0.0241(6) 0.0166(6) 0.0128(5) N8B 0.0572(6) 0.0549(6) 0.0531(6) 0.0240(5) 0.0211(5) 0.0088(5) C9B 0.0559(7) 0.0503(7) 0.0510(7) 0.0234(6) 0.0176(6) 0.0116(6) C10B 0.0742(9) 0.0650(9) 0.0519(8) 0.0195(7) 0.0227(7) 0.0094(7) C11B 0.0818(11) 0.0680(9) 0.0554(9) 0.0132(7) 0.0122(7) 0.0064(8) C12B 0.0670(9) 0.0633(9) 0.0690(10) 0.0179(7) 0.0066(7) -0.0023(7) C13B 0.0592(8) 0.0617(8) 0.0659(9) 0.0276(7) 0.0163(7) 0.0008(7) C14B 0.0551(7) 0.0495(7) 0.0500(7) 0.0248(6) 0.0157(6) 0.0122(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 N1 C2 1.3301(15) . ? N1 C6 1.3465(17) . ? C2 N7 1.3738(15) . ? C2 C3 1.4024(17) . ? C3 C4 1.3606(19) . ? C3 H3 0.9600 . ? C4 C5 1.384(2) . ? C4 H4 0.9601 . ? C5 C6 1.359(2) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.4035(15) . ? N7 H7 0.9000 . ? C8 C9 1.3916(16) . ? C8 C10 1.3927(15) . ? C9 C10 1.3792(17) 2 ? C9 H9 0.9602 . ? C10 C9 1.3792(17) 2 ? C10 H10 0.9600 . ? N1A C14A 1.3388(18) . ? N1A C2A 1.3406(18) . ? C2A C3A 1.420(2) . ? C2A C7A 1.432(2) . ? C3A C4A 1.356(3) . ? C3A H3A 0.9600 . ? C4A C5A 1.410(3) . ? C4A H4A 0.9600 . ? C5A C6A 1.349(2) . ? C5A H5A 0.9600 . ? C6A C7A 1.419(2) . ? C6A H6A 0.9599 . ? C7A N8A 1.3409(17) . ? N8A C9A 1.3421(18) . ? C9A C10A 1.4252(19) . ? C9A C14A 1.4302(19) . ? C10A C11A 1.355(2) . ? C10A H10A 0.9600 . ? C11A C12A 1.405(3) . ? C11A H11A 0.9600 . ? C12A C13A 1.345(2) . ? C12A H12A 0.9600 . ? C13A C14A 1.421(2) . ? C13A H13A 0.9600 . ? N1B C14B 1.3416(16) . ? N1B C2B 1.3439(16) . ? C2B C3B 1.4167(18) . ? C2B C7B 1.4296(17) . ? C3B C4B 1.349(2) . ? C3B H3B 0.9599 . ? C4B C5B 1.413(2) . ? C4B H4B 0.9600 . ? C5B C6B 1.354(2) . ? C5B H5B 0.9600 . ? C6B C7B 1.4216(18) . ? C6B H6B 0.9599 . ? C7B N8B 1.3402(16) . ? N8B C9B 1.3396(17) . ? C9B C10B 1.4222(19) . ? C9B C14B 1.4322(17) . ? C10B C11B 1.343(2) . ? C10B H10B 0.9599 . ? C11B C12B 1.413(2) . ? C11B H11B 0.9600 . ? C12B C13B 1.349(2) . ? C12B H12B 0.9600 . ? C13B C14B 1.4212(19) . ? C13B H13B 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 C2 N1 C6 116.56(11) . . ? N1 C2 N7 120.03(11) . . ? N1 C2 C3 122.64(11) . . ? N7 C2 C3 117.33(10) . . ? C4 C3 C2 118.82(12) . . ? C4 C3 H3 121.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.33(13) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 117.99(13) . . ? C6 C5 H5 122.5 . . ? C4 C5 H5 119.5 . . ? N1 C6 C5 124.65(13) . . ? N1 C6 H6 114.4 . . ? C5 C6 H6 121.0 . . ? C2 N7 C8 131.36(10) . . ? C2 N7 H7 115.8 . . ? C8 N7 H7 112.9 . . ? C9 C8 C10 117.49(11) . . ? C9 C8 N7 116.93(10) . . ? C10 C8 N7 125.56(11) . . ? C10 C9 C8 122.67(10) 2 . ? C10 C9 H9 118.8 2 . ? C8 C9 H9 118.5 . . ? C9 C10 C8 119.84(11) 2 . ? C9 C10 H10 120.9 2 . ? C8 C10 H10 119.3 . . ? C14A N1A C2A 116.77(12) . . ? N1A C2A C3A 119.52(14) . . ? N1A C2A C7A 121.96(12) . . ? C3A C2A C7A 118.51(14) . . ? C4A C3A C2A 120.04(16) . . ? C4A C3A H3A 124.7 . . ? C2A C3A H3A 115.1 . . ? C3A C4A C5A 121.15(16) . . ? C3A C4A H4A 120.6 . . ? C5A C4A H4A 118.2 . . ? C6A C5A C4A 120.97(16) . . ? C6A C5A H5A 119.4 . . ? C4A C5A H5A 119.6 . . ? C5A C6A C7A 119.97(16) . . ? C5A C6A H6A 123.9 . . ? C7A C6A H6A 116.0 . . ? N8A C7A C6A 119.31(14) . . ? N8A C7A C2A 121.35(13) . . ? C6A C7A C2A 119.35(14) . . ? C7A N8A C9A 116.48(12) . . ? N8A C9A C10A 119.49(13) . . ? N8A C9A C14A 122.18(12) . . ? C10A C9A C14A 118.33(14) . . ? C11A C10A C9A 119.87(16) . . ? C11A C10A H10A 125.9 . . ? C9A C10A H10A 114.2 . . ? C10A C11A C12A 121.45(15) . . ? C10A C11A H11A 120.9 . . ? C12A C11A H11A 117.6 . . ? C13A C12A C11A 120.87(16) . . ? C13A C12A H12A 119.0 . . ? C11A C12A H12A 120.1 . . ? C12A C13A C14A 120.15(16) . . ? C12A C13A H13A 120.8 . . ? C14A C13A H13A 119.0 . . ? N1A C14A C13A 119.45(13) . . ? N1A C14A C9A 121.25(13) . . ? C13A C14A C9A 119.30(13) . . ? C14B N1B C2B 117.15(10) . . ? N1B C2B C3B 119.67(11) . . ? N1B C2B C7B 121.28(12) . . ? C3B C2B C7B 119.04(12) . . ? C4B C3B C2B 120.35(13) . . ? C4B C3B H3B 123.2 . . ? C2B C3B H3B 116.4 . . ? C3B C4B C5B 120.75(14) . . ? C3B C4B H4B 121.7 . . ? C5B C4B H4B 117.5 . . ? C6B C5B C4B 121.10(14) . . ? C6B C5B H5B 118.5 . . ? C4B C5B H5B 120.4 . . ? C5B C6B C7B 119.95(13) . . ? C5B C6B H6B 123.1 . . ? C7B C6B H6B 116.9 . . ? N8B C7B C6B 119.54(12) . . ? N8B C7B C2B 121.68(12) . . ? C6B C7B C2B 118.78(12) . . ? C9B N8B C7B 116.91(11) . . ? N8B C9B C10B 119.70(12) . . ? N8B C9B C14B 121.69(12) . . ? C10B C9B C14B 118.61(12) . . ? C11B C10B C9B 120.33(14) . . ? C11B C10B H10B 124.4 . . ? C9B C10B H10B 115.2 . . ? C10B C11B C12B 121.19(14) . . ? C10B C11B H11B 118.3 . . ? C12B C11B H11B 120.5 . . ? C13B C12B C11B 120.75(14) . . ? C13B C12B H12B 120.0 . . ? C11B C12B H12B 119.2 . . ? C12B C13B C14B 120.29(13) . . ? C12B C13B H13B 122.9 . . ? C14B C13B H13B 116.8 . . ? N1B C14B C13B 119.98(12) . . ? N1B C14B C9B 121.21(12) . . ? C13B C14B C9B 118.80(12) . . ? 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 N7 H7 N1B 0.90 2.18 3.0747(13) 173.3 2_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.207 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.034 _chemical_name_common "N,N'-Bis(2-pyridyl)-1,4-diaminobenzene phenazine 1:4 complex" #===END data_2-phz _database_code_depnum_ccdc_archive 'CCDC 198838' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-4,4'-oxybis(aminobenzene) phenazine 1:2 complex ; _chemical_melting_point 157-158 _chemical_formula_moiety 'C22 H18 N4 O, 2(C12 H8 N2)' _chemical_formula_sum 'C46 H34 N8 O' _chemical_formula_weight 714.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1084(5) _cell_length_b 12.7044(7) _cell_length_c 20.4711(12) _cell_angle_alpha 86.329(5) _cell_angle_beta 81.084(5) _cell_angle_gamma 77.767(5) _cell_volume 1783.96(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6289 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% negligible _diffrn_reflns_number 13404 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6281 _reflns_number_gt 4922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.157a, 1999' _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation, Siemens Analytical X-Ray Instruments, Inc., 1989. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0554P)^2^+1.4041P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap,geom _refine_ls_hydrogen_treatment refu _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6281 _refine_ls_number_parameters 530 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 N1 N 1.3565(2) 0.14241(14) 0.00829(8) 0.0299(4) Uani 1 1 d . . . C2 C 1.3244(3) 0.21939(16) 0.05231(9) 0.0267(4) Uani 1 1 d . . . C3 C 1.4537(3) 0.28964(17) 0.05319(11) 0.0327(5) Uani 1 1 d . . . H3 H 1.4228 0.3432 0.0864 0.041(7) Uiso 1 1 d R . . C4 C 1.6170(3) 0.2786(2) 0.00705(11) 0.0393(5) Uani 1 1 d . . . H4 H 1.7049 0.3267 0.0066 0.050(7) Uiso 1 1 d R . . C5 C 1.6533(3) 0.19835(19) -0.03920(11) 0.0369(5) Uani 1 1 d . . . H5 H 1.7674 0.1875 -0.0719 0.035(6) Uiso 1 1 d R . . C6 C 1.5201(3) 0.13291(19) -0.03618(10) 0.0344(5) Uani 1 1 d . . . H6 H 1.5406 0.0773 -0.0677 0.039(6) Uiso 1 1 d R . . N7 N 1.1584(2) 0.23408(14) 0.09857(8) 0.0294(4) Uani 1 1 d . . . H7 H 1.1450 0.2875 0.1268 0.039(6) Uiso 1 1 d R . . C8 C 1.0079(3) 0.17648(15) 0.11243(9) 0.0245(4) Uani 1 1 d . . . C9 C 0.8641(3) 0.21091(16) 0.16583(9) 0.0260(4) Uani 1 1 d . . . H9 H 0.8686 0.2718 0.1906 0.030(6) Uiso 1 1 d R . . C10 C 0.7103(3) 0.15928(17) 0.18466(10) 0.0289(5) Uani 1 1 d . . . H10 H 0.6092 0.1849 0.2202 0.035(6) Uiso 1 1 d R . . C11 C 0.6998(3) 0.07030(17) 0.15033(9) 0.0287(5) Uani 1 1 d . . . C12 C 0.8402(3) 0.03579(17) 0.09709(10) 0.0296(5) Uani 1 1 d . . . H12 H 0.8251 -0.0229 0.0724 0.033(6) Uiso 1 1 d R . . C13 C 0.9944(3) 0.08734(16) 0.07783(10) 0.0276(4) Uani 1 1 d . . . H13 H 1.0942 0.0651 0.0412 0.026(5) Uiso 1 1 d R . . O14 O 0.5437(2) 0.01771(14) 0.16200(7) 0.0405(4) Uani 1 1 d . . . C15 C 0.4437(3) 0.00727(16) 0.22482(10) 0.0277(4) Uani 1 1 d . . . C16 C 0.5288(3) -0.00813(16) 0.28221(10) 0.0285(4) Uani 1 1 d . . . H16 H 0.6634 -0.0060 0.2811 0.032(6) Uiso 1 1 d R . . C17 C 0.4176(3) -0.02542(16) 0.34253(10) 0.0275(4) Uani 1 1 d . . . H17 H 0.4730 -0.0354 0.3829 0.025(5) Uiso 1 1 d R . . C18 C 0.2208(3) -0.02722(16) 0.34629(9) 0.0248(4) Uani 1 1 d . . . C19 C 0.1384(3) -0.01043(17) 0.28784(10) 0.0294(5) Uani 1 1 d . . . H19 H 0.0017 -0.0076 0.2896 0.033(6) Uiso 1 1 d R . . C20 C 0.2484(3) 0.00530(16) 0.22781(10) 0.0274(4) Uani 1 1 d . . . H20 H 0.1902 0.0177 0.1880 0.034(6) Uiso 1 1 d R . . N21 N 0.1092(3) -0.04154(15) 0.40833(8) 0.0310(4) Uani 1 1 d . . . H21 H 0.1303 -0.0083 0.4432 0.043(7) Uiso 1 1 d R . . C22 C -0.0351(3) -0.10029(16) 0.42018(9) 0.0243(4) Uani 1 1 d . . . N23 N -0.1598(2) -0.07809(13) 0.47656(8) 0.0270(4) Uani 1 1 d . . . C24 C -0.2979(3) -0.13802(17) 0.49251(10) 0.0292(5) Uani 1 1 d . . . H24 H -0.3846 -0.1209 0.5330 0.027(5) Uiso 1 1 d R . . C25 C -0.3190(3) -0.21918(17) 0.45476(10) 0.0300(5) Uani 1 1 d . . . H25 H -0.4205 -0.2590 0.4667 0.033(6) Uiso 1 1 d R . . C26 C -0.1900(3) -0.24100(16) 0.39660(10) 0.0274(4) Uani 1 1 d . . . H26 H -0.1985 -0.2981 0.3694 0.032(6) Uiso 1 1 d R . . C27 C -0.0475(3) -0.18175(16) 0.37861(10) 0.0274(4) Uani 1 1 d . . . H27 H 0.0477 -0.1973 0.3399 0.038(6) Uiso 1 1 d R . . N1B N 0.6562(2) 0.37635(13) 0.28945(8) 0.0268(4) Uani 1 1 d . . . C2B C 0.5903(3) 0.47999(17) 0.27239(10) 0.0266(4) Uani 1 1 d . . . C3B C 0.5517(3) 0.50720(18) 0.20636(10) 0.0322(5) Uani 1 1 d . . . H3B H 0.5764 0.4491 0.1764 0.034(6) Uiso 1 1 d R . . C4B C 0.4816(3) 0.6114(2) 0.18807(12) 0.0385(5) Uani 1 1 d . . . H4B H 0.4543 0.6322 0.1440 0.031(6) Uiso 1 1 d R . . C5B C 0.4453(3) 0.69419(19) 0.23471(12) 0.0402(6) Uani 1 1 d . . . H5B H 0.3922 0.7670 0.2217 0.049(7) Uiso 1 1 d R . . C6B C 0.4812(3) 0.67220(17) 0.29798(12) 0.0339(5) Uani 1 1 d . . . H6B H 0.4607 0.7284 0.3291 0.043(7) Uiso 1 1 d R . . C7B C 0.5570(3) 0.56454(16) 0.31886(10) 0.0266(4) Uani 1 1 d . . . N8B N 0.5960(2) 0.54396(14) 0.38129(8) 0.0284(4) Uani 1 1 d . . . C9B C 0.6634(3) 0.44054(16) 0.39837(10) 0.0260(4) Uani 1 1 d . . . C10B C 0.7085(3) 0.41283(19) 0.46352(10) 0.0337(5) Uani 1 1 d . . . H10B H 0.6963 0.4705 0.4930 0.041(7) Uiso 1 1 d R . . C11B C 0.7699(3) 0.3090(2) 0.48202(11) 0.0384(5) Uani 1 1 d . . . H11B H 0.8001 0.2901 0.5259 0.048(7) Uiso 1 1 d R . . C12B C 0.7913(3) 0.2243(2) 0.43749(12) 0.0401(6) Uani 1 1 d . . . H12B H 0.8362 0.1515 0.4526 0.044(7) Uiso 1 1 d R . . C13B C 0.7544(3) 0.24692(17) 0.37431(11) 0.0343(5) Uani 1 1 d . . . H13B H 0.7745 0.1912 0.3429 0.040(6) Uiso 1 1 d R . . C14B C 0.6907(3) 0.35565(16) 0.35241(10) 0.0260(4) Uani 1 1 d . . . N1A N 1.1051(2) 0.42199(13) 0.18730(8) 0.0270(4) Uani 1 1 d . . . C2A C 1.0365(3) 0.52281(16) 0.16564(10) 0.0256(4) Uani 1 1 d . . . C3A C 1.0005(3) 0.54140(19) 0.09884(11) 0.0357(5) Uani 1 1 d . . . H3A H 1.0294 0.4799 0.0713 0.045(7) Uiso 1 1 d R . . C4A C 0.9267(3) 0.6424(2) 0.07665(12) 0.0419(6) Uani 1 1 d . . . H4A H 0.9005 0.6543 0.0318 0.049(7) Uiso 1 1 d R . . C5A C 0.8846(3) 0.7309(2) 0.11933(12) 0.0414(6) Uani 1 1 d . . . H5A H 0.8294 0.8007 0.1020 0.049(7) Uiso 1 1 d R . . C6A C 0.9185(3) 0.71691(18) 0.18325(11) 0.0347(5) Uani 1 1 d . . . H6A H 0.8887 0.7749 0.2135 0.038(6) Uiso 1 1 d R . . C7A C 0.9954(3) 0.61250(16) 0.20845(10) 0.0264(4) Uani 1 1 d . . . N8A N 1.0264(2) 0.59929(13) 0.27204(8) 0.0269(4) Uani 1 1 d . . . C9A C 1.0960(3) 0.49815(16) 0.29361(9) 0.0243(4) Uani 1 1 d . . . C10A C 1.1321(3) 0.47949(18) 0.36050(10) 0.0311(5) Uani 1 1 d . . . H10A H 1.1065 0.5416 0.3873 0.034(6) Uiso 1 1 d R . . C11A C 1.1986(3) 0.37808(19) 0.38340(11) 0.0358(5) Uani 1 1 d . . . H11A H 1.2185 0.3655 0.4288 0.035(6) Uiso 1 1 d R . . C12A C 1.2333(3) 0.28916(19) 0.34135(12) 0.0370(5) Uani 1 1 d . . . H12A H 1.2745 0.2171 0.3582 0.042(7) Uiso 1 1 d R . . C13A C 1.2034(3) 0.30335(17) 0.27712(11) 0.0319(5) Uani 1 1 d . . . H13A H 1.2221 0.2445 0.2480 0.035(6) Uiso 1 1 d R . . C14A C 1.1347(3) 0.40880(16) 0.25107(10) 0.0253(4) 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 N1 0.0292(9) 0.0337(10) 0.0253(9) -0.0030(7) -0.0012(7) -0.0042(7) C2 0.0281(10) 0.0299(11) 0.0210(10) 0.0009(8) -0.0038(8) -0.0038(8) C3 0.0353(12) 0.0326(12) 0.0325(11) -0.0025(9) -0.0065(9) -0.0106(9) C4 0.0345(12) 0.0453(14) 0.0405(13) 0.0030(10) -0.0044(10) -0.0159(10) C5 0.0300(11) 0.0448(13) 0.0326(12) 0.0041(10) -0.0009(9) -0.0044(10) C6 0.0348(12) 0.0404(12) 0.0259(11) -0.0033(9) -0.0012(9) -0.0045(10) N7 0.0325(9) 0.0312(9) 0.0257(9) -0.0077(7) 0.0021(7) -0.0121(8) C8 0.0270(10) 0.0240(10) 0.0228(10) 0.0004(8) -0.0046(8) -0.0051(8) C9 0.0287(10) 0.0272(10) 0.0219(10) -0.0039(8) -0.0025(8) -0.0054(8) C10 0.0279(10) 0.0343(11) 0.0230(10) -0.0035(8) 0.0001(8) -0.0054(9) C11 0.0307(11) 0.0381(12) 0.0201(10) 0.0009(8) -0.0016(8) -0.0153(9) C12 0.0432(12) 0.0276(11) 0.0208(10) -0.0050(8) -0.0034(9) -0.0130(9) C13 0.0331(11) 0.0270(10) 0.0221(10) -0.0009(8) -0.0009(8) -0.0069(9) O14 0.0478(9) 0.0604(11) 0.0213(7) -0.0070(7) 0.0040(7) -0.0336(8) C15 0.0325(11) 0.0286(11) 0.0229(10) -0.0040(8) 0.0017(8) -0.0115(9) C16 0.0260(10) 0.0323(11) 0.0279(11) -0.0029(8) -0.0020(8) -0.0086(9) C17 0.0299(11) 0.0304(11) 0.0231(10) 0.0000(8) -0.0081(8) -0.0055(9) C18 0.0274(10) 0.0251(10) 0.0228(10) -0.0039(8) -0.0006(8) -0.0087(8) C19 0.0245(10) 0.0330(11) 0.0316(11) -0.0005(9) -0.0053(8) -0.0067(9) C20 0.0311(11) 0.0295(11) 0.0239(10) 0.0032(8) -0.0088(8) -0.0091(9) N21 0.0349(10) 0.0400(10) 0.0227(9) -0.0074(7) 0.0013(7) -0.0202(8) C22 0.0256(10) 0.0273(10) 0.0207(9) -0.0011(8) -0.0027(8) -0.0070(8) N23 0.0288(9) 0.0291(9) 0.0241(9) -0.0027(7) -0.0032(7) -0.0082(7) C24 0.0308(11) 0.0334(11) 0.0225(10) -0.0006(8) -0.0008(8) -0.0068(9) C25 0.0294(11) 0.0323(11) 0.0292(11) 0.0023(9) -0.0036(8) -0.0100(9) C26 0.0303(11) 0.0247(10) 0.0293(11) -0.0029(8) -0.0091(8) -0.0061(8) C27 0.0279(10) 0.0300(11) 0.0235(10) -0.0047(8) -0.0010(8) -0.0051(8) N1B 0.0220(8) 0.0278(9) 0.0292(9) -0.0036(7) -0.0006(7) -0.0039(7) C2B 0.0162(9) 0.0330(11) 0.0300(11) -0.0033(8) -0.0001(8) -0.0052(8) C3B 0.0240(10) 0.0414(13) 0.0304(11) -0.0012(9) -0.0015(8) -0.0066(9) C4B 0.0277(11) 0.0512(14) 0.0370(12) 0.0094(11) -0.0068(9) -0.0103(10) C5B 0.0278(11) 0.0369(13) 0.0557(15) 0.0113(11) -0.0083(10) -0.0081(10) C6B 0.0256(11) 0.0281(11) 0.0486(14) -0.0024(10) -0.0055(9) -0.0067(9) C7B 0.0178(9) 0.0284(11) 0.0341(11) -0.0011(8) -0.0025(8) -0.0067(8) N8B 0.0244(9) 0.0307(9) 0.0313(9) -0.0059(7) -0.0020(7) -0.0080(7) C9B 0.0186(9) 0.0329(11) 0.0271(10) -0.0029(8) 0.0008(8) -0.0090(8) C10B 0.0288(11) 0.0442(13) 0.0285(11) -0.0017(10) -0.0019(9) -0.0099(10) C11B 0.0271(11) 0.0558(15) 0.0305(12) 0.0096(10) -0.0032(9) -0.0086(10) C12B 0.0309(12) 0.0402(13) 0.0454(14) 0.0116(11) -0.0045(10) -0.0032(10) C13B 0.0309(11) 0.0297(11) 0.0391(12) -0.0024(9) -0.0008(9) -0.0018(9) C14B 0.0184(9) 0.0314(11) 0.0261(10) -0.0016(8) 0.0021(8) -0.0040(8) N1A 0.0255(9) 0.0286(9) 0.0284(9) -0.0051(7) -0.0027(7) -0.0085(7) C2A 0.0211(10) 0.0289(11) 0.0283(10) 0.0002(8) -0.0029(8) -0.0095(8) C3A 0.0334(12) 0.0465(14) 0.0282(11) 0.0001(10) -0.0051(9) -0.0105(10) C4A 0.0424(13) 0.0540(15) 0.0316(12) 0.0121(11) -0.0119(10) -0.0140(11) C5A 0.0368(13) 0.0405(13) 0.0484(14) 0.0152(11) -0.0113(11) -0.0122(10) C6A 0.0298(11) 0.0304(11) 0.0444(13) 0.0029(10) -0.0057(10) -0.0078(9) C7A 0.0195(9) 0.0282(11) 0.0315(11) 0.0005(8) -0.0018(8) -0.0069(8) N8A 0.0224(8) 0.0294(9) 0.0286(9) -0.0049(7) -0.0008(7) -0.0059(7) C9A 0.0178(9) 0.0303(11) 0.0251(10) -0.0026(8) -0.0008(7) -0.0063(8) C10A 0.0239(10) 0.0420(13) 0.0266(11) -0.0058(9) 0.0000(8) -0.0062(9) C11A 0.0269(11) 0.0519(14) 0.0288(11) 0.0086(10) -0.0056(9) -0.0107(10) C12A 0.0281(11) 0.0349(12) 0.0482(14) 0.0111(10) -0.0099(10) -0.0076(9) C13A 0.0276(11) 0.0257(11) 0.0441(13) -0.0002(9) -0.0082(9) -0.0074(9) C14A 0.0191(9) 0.0289(11) 0.0278(10) -0.0001(8) -0.0015(8) -0.0063(8) _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 N1 C2 1.332(3) . ? N1 C6 1.350(3) . ? C2 N7 1.381(3) . ? C2 C3 1.413(3) . ? C3 C4 1.366(3) . ? C3 H3 0.9600 . ? C4 C5 1.393(3) . ? C4 H4 0.9600 . ? C5 C6 1.379(3) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.404(3) . ? N7 H7 0.9001 . ? C8 C9 1.399(3) . ? C8 C13 1.401(3) . ? C9 C10 1.384(3) . ? C9 H9 0.9600 . ? C10 C11 1.390(3) . ? C10 H10 0.9600 . ? C11 C12 1.384(3) . ? C11 O14 1.395(2) . ? C12 C13 1.387(3) . ? C12 H12 0.9600 . ? C13 H13 0.9600 . ? O14 C15 1.383(2) . ? C15 C20 1.385(3) . ? C15 C16 1.388(3) . ? C16 C17 1.391(3) . ? C16 H16 0.9600 . ? C17 C18 1.394(3) . ? C17 H17 0.9601 . ? C18 C19 1.397(3) . ? C18 N21 1.412(2) . ? C19 C20 1.378(3) . ? C19 H19 0.9600 . ? C20 H20 0.9600 . ? N21 C22 1.376(3) . ? N21 H21 0.9000 . ? C22 N23 1.348(2) . ? C22 C27 1.406(3) . ? N23 C24 1.355(3) . ? C24 C25 1.374(3) . ? C24 H24 0.9600 . ? C25 C26 1.390(3) . ? C25 H25 0.9600 . ? C26 C27 1.379(3) . ? C26 H26 0.9600 . ? C27 H27 0.9601 . ? N1B C2B 1.344(3) . ? N1B C14B 1.348(3) . ? C2B C3B 1.427(3) . ? C2B C7B 1.438(3) . ? C3B C4B 1.362(3) . ? C3B H3B 0.9600 . ? C4B C5B 1.422(3) . ? C4B H4B 0.9601 . ? C5B C6B 1.359(3) . ? C5B H5B 0.9600 . ? C6B C7B 1.424(3) . ? C6B H6B 0.9599 . ? C7B N8B 1.347(3) . ? N8B C9B 1.343(3) . ? C9B C10B 1.425(3) . ? C9B C14B 1.439(3) . ? C10B C11B 1.348(3) . ? C10B H10B 0.9599 . ? C11B C12B 1.423(3) . ? C11B H11B 0.9600 . ? C12B C13B 1.360(3) . ? C12B H12B 0.9600 . ? C13B C14B 1.426(3) . ? C13B H13B 0.9601 . ? N1A C2A 1.343(3) . ? N1A C14A 1.349(3) . ? C2A C3A 1.426(3) . ? C2A C7A 1.435(3) . ? C3A C4A 1.357(3) . ? C3A H3A 0.9600 . ? C4A C5A 1.421(4) . ? C4A H4A 0.9600 . ? C5A C6A 1.361(3) . ? C5A H5A 0.9600 . ? C6A C7A 1.420(3) . ? C6A H6A 0.9599 . ? C7A N8A 1.348(3) . ? N8A C9A 1.348(3) . ? C9A C10A 1.428(3) . ? C9A C14A 1.429(3) . ? C10A C11A 1.355(3) . ? C10A H10A 0.9599 . ? C11A C12A 1.421(3) . ? C11A H11A 0.9601 . ? C12A C13A 1.359(3) . ? C12A H12A 0.9600 . ? C13A C14A 1.425(3) . ? C13A H13A 0.9601 . ? 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 N1 C6 117.35(18) . . ? N1 C2 N7 120.12(18) . . ? N1 C2 C3 122.34(19) . . ? N7 C2 C3 117.53(18) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3 122.8 . . ? C2 C3 H3 118.3 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 117.7(2) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 122.0 . . ? N1 C6 C5 124.2(2) . . ? N1 C6 H6 116.3 . . ? C5 C6 H6 119.6 . . ? C2 N7 C8 131.51(17) . . ? C2 N7 H7 115.9 . . ? C8 N7 H7 112.5 . . ? C9 C8 C13 118.60(18) . . ? C9 C8 N7 116.40(17) . . ? C13 C8 N7 124.99(18) . . ? C10 C9 C8 121.50(18) . . ? C10 C9 H9 117.7 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 119.30(18) . . ? C9 C10 H10 121.3 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 119.86(18) . . ? C12 C11 O14 116.08(18) . . ? C10 C11 O14 123.78(18) . . ? C11 C12 C13 121.14(18) . . ? C11 C12 H12 118.3 . . ? C13 C12 H12 120.5 . . ? C12 C13 C8 119.60(18) . . ? C12 C13 H13 123.0 . . ? C8 C13 H13 117.3 . . ? C15 O14 C11 121.65(15) . . ? O14 C15 C20 115.54(18) . . ? O14 C15 C16 124.41(19) . . ? C20 C15 C16 119.90(18) . . ? C15 C16 C17 119.83(19) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 119.3 . . ? C16 C17 C18 120.88(18) . . ? C16 C17 H17 121.3 . . ? C18 C17 H17 117.8 . . ? C17 C18 C19 118.10(18) . . ? C17 C18 N21 119.92(18) . . ? C19 C18 N21 121.94(18) . . ? C20 C19 C18 121.29(19) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.5 . . ? C19 C20 C15 119.99(18) . . ? C19 C20 H20 120.7 . . ? C15 C20 H20 119.3 . . ? C22 N21 C18 125.47(16) . . ? C22 N21 H21 116.2 . . ? C18 N21 H21 118.3 . . ? N23 C22 N21 115.23(17) . . ? N23 C22 C27 121.75(17) . . ? N21 C22 C27 122.94(17) . . ? C22 N23 C24 117.61(17) . . ? N23 C24 C25 124.16(19) . . ? N23 C24 H24 116.1 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 117.69(19) . . ? C24 C25 H25 122.3 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 119.91(19) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.1 . . ? C26 C27 C22 118.88(18) . . ? C26 C27 H27 121.8 . . ? C22 C27 H27 119.3 . . ? C2B N1B C14B 116.52(17) . . ? N1B C2B C3B 119.21(19) . . ? N1B C2B C7B 121.87(18) . . ? C3B C2B C7B 118.91(19) . . ? C4B C3B C2B 120.4(2) . . ? C4B C3B H3B 122.6 . . ? C2B C3B H3B 117.0 . . ? C3B C4B C5B 120.3(2) . . ? C3B C4B H4B 122.3 . . ? C5B C4B H4B 117.4 . . ? C6B C5B C4B 121.4(2) . . ? C6B C5B H5B 119.0 . . ? C4B C5B H5B 119.7 . . ? C5B C6B C7B 120.1(2) . . ? C5B C6B H6B 121.4 . . ? C7B C6B H6B 118.4 . . ? N8B C7B C6B 119.65(19) . . ? N8B C7B C2B 121.47(18) . . ? C6B C7B C2B 118.87(19) . . ? C9B N8B C7B 116.81(17) . . ? N8B C9B C10B 119.90(19) . . ? N8B C9B C14B 121.61(18) . . ? C10B C9B C14B 118.50(19) . . ? C11B C10B C9B 120.5(2) . . ? C11B C10B H10B 121.7 . . ? C9B C10B H10B 117.7 . . ? C10B C11B C12B 121.3(2) . . ? C10B C11B H11B 120.7 . . ? C12B C11B H11B 118.0 . . ? C13B C12B C11B 120.3(2) . . ? C13B C12B H12B 121.0 . . ? C11B C12B H12B 118.6 . . ? C12B C13B C14B 120.3(2) . . ? C12B C13B H13B 121.6 . . ? C14B C13B H13B 118.1 . . ? N1B C14B C13B 119.31(18) . . ? N1B C14B C9B 121.66(18) . . ? C13B C14B C9B 119.02(18) . . ? C2A N1A C14A 117.02(17) . . ? N1A C2A C3A 119.46(19) . . ? N1A C2A C7A 121.58(18) . . ? C3A C2A C7A 118.95(19) . . ? C4A C3A C2A 120.2(2) . . ? C4A C3A H3A 122.7 . . ? C2A C3A H3A 117.1 . . ? C3A C4A C5A 120.7(2) . . ? C3A C4A H4A 119.8 . . ? C5A C4A H4A 119.4 . . ? C6A C5A C4A 121.0(2) . . ? C6A C5A H5A 120.9 . . ? C4A C5A H5A 118.1 . . ? C5A C6A C7A 120.0(2) . . ? C5A C6A H6A 122.8 . . ? C7A C6A H6A 117.1 . . ? N8A C7A C6A 119.59(19) . . ? N8A C7A C2A 121.32(18) . . ? C6A C7A C2A 119.08(19) . . ? C7A N8A C9A 117.02(17) . . ? N8A C9A C10A 119.40(18) . . ? N8A C9A C14A 121.54(17) . . ? C10A C9A C14A 119.06(18) . . ? C11A C10A C9A 120.2(2) . . ? C11A C10A H10A 123.2 . . ? C9A C10A H10A 116.6 . . ? C10A C11A C12A 120.6(2) . . ? C10A C11A H11A 120.0 . . ? C12A C11A H11A 119.3 . . ? C13A C12A C11A 121.2(2) . . ? C13A C12A H12A 118.3 . . ? C11A C12A H12A 120.5 . . ? C12A C13A C14A 119.9(2) . . ? C12A C13A H13A 122.9 . . ? C14A C13A H13A 117.2 . . ? N1A C14A C13A 119.46(18) . . ? N1A C14A C9A 121.51(18) . . ? C13A C14A C9A 119.02(18) . . ? 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 N7 H7 N1A 0.90 2.12 3.017(2) 175.4 . N21 H21 N23 0.90 2.09 2.991(2) 175.5 2_556 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.265 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.053 _chemical_name_common ;N,N'-Bis(2-pyridyl)-4,4'-oxybis(aminobenzene) phenazine 1:2 complex ; #===END data_3-phz _database_code_depnum_ccdc_archive 'CCDC 198839' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-4,4'-sulphonyldianiline phenazine 1:1 complex ; _chemical_melting_point 204-205 _chemical_formula_moiety 'C22 H18 N4 O2 S, C12 H8 N2' _chemical_formula_sum 'C34 H26 N6 O2 S' _chemical_formula_weight 582.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 14.1875(8) _cell_length_b 8.7245(5) _cell_length_c 23.0060(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.831(5) _cell_angle_gamma 90.00 _cell_volume 2787.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4833 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.161 _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 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% negligible _diffrn_reflns_number 14433 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4909 _reflns_number_gt 3383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.157a, 1999' _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation, Siemens Analytical X-Ray Instruments, Inc., 1989. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0494P)^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,difmap _refine_ls_hydrogen_treatment refu _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4909 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _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 N1A N 0.15659(11) 0.11799(17) 0.04481(7) 0.0253(4) Uani 1 1 d . . . C2A C 0.14614(13) 0.1667(2) -0.01155(8) 0.0244(4) Uani 1 1 d . . . C3A C 0.16294(14) 0.3228(2) -0.02307(10) 0.0342(5) Uani 1 1 d . . . H3AA H 0.1817 0.3933 0.0093 0.042(6) Uiso 1 1 d R . . C4A C 0.15288(15) 0.3729(3) -0.08010(11) 0.0442(6) Uani 1 1 d . . . H4AA H 0.1638 0.4790 -0.0877 0.044(6) Uiso 1 1 d R . . C5A C 0.12623(16) 0.2702(3) -0.12835(11) 0.0496(7) Uani 1 1 d . . . H5AA H 0.1200 0.3072 -0.1683 0.063(7) Uiso 1 1 d R . . C6A C 0.10946(15) 0.1212(3) -0.11901(10) 0.0420(6) Uani 1 1 d . . . H6AA H 0.0917 0.0531 -0.1522 0.053(7) Uiso 1 1 d R . . C7A C 0.11769(13) 0.0642(2) -0.06034(9) 0.0280(5) Uani 1 1 d . . . N8A N 0.09841(12) -0.08447(19) -0.05201(8) 0.0337(4) Uani 1 1 d . . . C9A C 0.10803(13) -0.1322(2) 0.00451(9) 0.0289(5) Uani 1 1 d . . . C10A C 0.08692(15) -0.2862(2) 0.01638(12) 0.0431(6) Uani 1 1 d . . . H10A H 0.0647 -0.3559 -0.0158 0.048(7) Uiso 1 1 d R . . C11A C 0.09789(16) -0.3358(3) 0.07324(13) 0.0520(7) Uani 1 1 d . . . H11A H 0.0830 -0.4403 0.0808 0.052(7) Uiso 1 1 d R . . C12A C 0.13076(16) -0.2368(3) 0.12158(12) 0.0466(6) Uani 1 1 d . . . H12A H 0.1390 -0.2752 0.1614 0.056(7) Uiso 1 1 d R . . C13A C 0.15093(15) -0.0886(2) 0.11247(10) 0.0367(5) Uani 1 1 d . . . H13A H 0.1732 -0.0220 0.1457 0.039(6) Uiso 1 1 d R . . C14A C 0.13879(13) -0.0310(2) 0.05337(9) 0.0249(4) Uani 1 1 d . . . N1 N 0.60286(11) 1.02038(17) -0.03737(7) 0.0264(4) Uani 1 1 d . . . C2 C 0.63605(13) 1.1136(2) 0.00800(8) 0.0243(4) Uani 1 1 d . . . C3 C 0.66135(14) 1.2670(2) 0.00019(10) 0.0321(5) Uani 1 1 d . . . H3A H 0.6855 1.3313 0.0338 0.035(6) Uiso 1 1 d R . . C4 C 0.65093(15) 1.3220(2) -0.05652(10) 0.0366(5) Uani 1 1 d . . . H4A H 0.6678 1.4262 -0.0631 0.044(6) Uiso 1 1 d R . . C5 C 0.61556(15) 1.2270(2) -0.10425(10) 0.0355(5) Uani 1 1 d . . . H5A H 0.6075 1.2632 -0.1444 0.029(5) Uiso 1 1 d R . . C6 C 0.59289(14) 1.0795(2) -0.09196(9) 0.0316(5) Uani 1 1 d . . . H6A H 0.5679 1.0138 -0.1250 0.030(5) Uiso 1 1 d R . . N7 N 0.64732(11) 1.06069(16) 0.06584(7) 0.0251(4) Uani 1 1 d . . . H7A H 0.6626 1.1341 0.0937 0.033(6) Uiso 1 1 d R . . C8 C 0.63933(12) 0.91497(19) 0.08868(8) 0.0210(4) Uani 1 1 d . . . C9 C 0.66309(13) 0.9017(2) 0.15050(8) 0.0241(4) Uani 1 1 d . . . H9A H 0.6814 0.9916 0.1741 0.021(5) Uiso 1 1 d R . . C10 C 0.66070(13) 0.7624(2) 0.17815(8) 0.0241(4) Uani 1 1 d . . . H10B H 0.6772 0.7548 0.2206 0.023(5) Uiso 1 1 d R . . C11 C 0.63383(13) 0.6322(2) 0.14353(8) 0.0227(4) Uani 1 1 d . . . C12 C 0.60807(13) 0.6451(2) 0.08213(8) 0.0242(4) Uani 1 1 d . . . H12B H 0.5882 0.5552 0.0587 0.026(5) Uiso 1 1 d R . . C13 C 0.61070(13) 0.7842(2) 0.05430(8) 0.0232(4) Uani 1 1 d . . . H13B H 0.5931 0.7916 0.0118 0.019(5) Uiso 1 1 d R . . S14 S 0.63278(4) 0.45400(5) 0.17867(2) 0.02890(15) Uani 1 1 d . . . O1 O 0.67530(10) 0.47341(15) 0.24045(6) 0.0372(4) Uani 1 1 d . . . O2 O 0.67357(10) 0.34145(14) 0.14479(6) 0.0344(4) Uani 1 1 d . . . C15 C 0.51102(14) 0.4085(2) 0.17286(8) 0.0256(5) Uani 1 1 d . . . C16 C 0.46074(15) 0.4691(2) 0.21325(8) 0.0302(5) Uani 1 1 d . . . H16A H 0.4944 0.5308 0.2454 0.029(5) Uiso 1 1 d R . . C17 C 0.36373(15) 0.4426(2) 0.20833(8) 0.0295(5) Uani 1 1 d . . . H17A H 0.3303 0.4853 0.2369 0.029(5) Uiso 1 1 d R . . C18 C 0.31388(14) 0.3524(2) 0.16135(8) 0.0253(5) Uani 1 1 d . . . C19 C 0.36530(14) 0.2913(2) 0.12064(8) 0.0253(5) Uani 1 1 d . . . H19A H 0.3322 0.2293 0.0884 0.025(5) Uiso 1 1 d R . . C20 C 0.46218(14) 0.3186(2) 0.12606(8) 0.0267(5) Uani 1 1 d . . . H20A H 0.4961 0.2760 0.0978 0.033(6) Uiso 1 1 d R . . N21 N 0.21676(12) 0.31583(17) 0.15158(7) 0.0297(4) Uani 1 1 d . . . H21A H 0.1966 0.2536 0.1203 0.047(7) Uiso 1 1 d R . . C22 C 0.14502(15) 0.3580(2) 0.18147(8) 0.0283(5) Uani 1 1 d . . . N23 N 0.16566(13) 0.45651(19) 0.22639(7) 0.0374(5) Uani 1 1 d . . . C24 C 0.09199(19) 0.4960(3) 0.25213(10) 0.0452(6) Uani 1 1 d . . . H24A H 0.1050 0.5680 0.2843 0.055(7) Uiso 1 1 d R . . C25 C 0.00004(18) 0.4420(2) 0.23582(10) 0.0421(6) Uani 1 1 d . . . H25A H -0.0493 0.4746 0.2560 0.062(7) Uiso 1 1 d R . . C26 C -0.01999(17) 0.3382(2) 0.18908(9) 0.0369(5) Uani 1 1 d . . . H26A H -0.0838 0.2975 0.1763 0.040(6) Uiso 1 1 d R . . C27 C 0.05310(15) 0.2952(2) 0.16154(9) 0.0318(5) Uani 1 1 d . . . H27A H 0.0413 0.2234 0.1293 0.033(5) Uiso 1 1 d 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 N1A 0.0238(9) 0.0255(9) 0.0271(9) -0.0019(7) 0.0065(7) -0.0014(7) C2A 0.0161(10) 0.0298(11) 0.0278(11) 0.0006(9) 0.0057(8) 0.0008(8) C3A 0.0248(12) 0.0306(12) 0.0469(14) 0.0056(11) 0.0068(10) -0.0007(9) C4A 0.0286(13) 0.0443(15) 0.0606(17) 0.0224(13) 0.0115(11) 0.0042(11) C5A 0.0321(14) 0.0786(19) 0.0401(15) 0.0269(14) 0.0120(11) 0.0122(13) C6A 0.0341(14) 0.0652(17) 0.0262(12) -0.0010(12) 0.0050(10) 0.0092(12) C7A 0.0181(11) 0.0363(12) 0.0296(12) -0.0047(9) 0.0048(8) 0.0018(9) N8A 0.0270(10) 0.0349(11) 0.0371(11) -0.0113(8) 0.0014(8) 0.0018(8) C9A 0.0185(11) 0.0259(11) 0.0415(13) -0.0027(10) 0.0040(9) 0.0015(8) C10A 0.0286(13) 0.0225(12) 0.0751(19) -0.0027(12) 0.0037(12) -0.0012(10) C11A 0.0331(14) 0.0282(13) 0.097(2) 0.0211(14) 0.0177(14) 0.0005(11) C12A 0.0393(15) 0.0458(15) 0.0597(17) 0.0225(13) 0.0215(12) 0.0091(12) C13A 0.0371(14) 0.0392(13) 0.0361(13) 0.0062(11) 0.0132(10) 0.0054(10) C14A 0.0176(11) 0.0251(11) 0.0329(12) 0.0006(9) 0.0074(8) 0.0012(9) N1 0.0295(10) 0.0257(9) 0.0244(9) 0.0031(7) 0.0064(7) 0.0026(7) C2 0.0182(10) 0.0234(10) 0.0314(12) 0.0041(9) 0.0054(8) 0.0040(8) C3 0.0259(12) 0.0228(11) 0.0452(14) 0.0060(10) 0.0021(10) -0.0010(9) C4 0.0320(13) 0.0241(12) 0.0549(16) 0.0155(11) 0.0117(11) 0.0013(9) C5 0.0364(13) 0.0343(12) 0.0380(14) 0.0158(11) 0.0127(10) 0.0087(10) C6 0.0350(13) 0.0307(12) 0.0295(12) 0.0059(10) 0.0077(9) 0.0091(10) N7 0.0288(10) 0.0182(8) 0.0267(9) -0.0015(7) 0.0017(7) -0.0033(7) C8 0.0163(10) 0.0194(10) 0.0268(11) 0.0010(8) 0.0033(8) -0.0008(8) C9 0.0245(11) 0.0202(10) 0.0255(11) -0.0062(8) 0.0005(8) -0.0023(8) C10 0.0248(11) 0.0240(11) 0.0220(11) -0.0004(8) 0.0011(8) -0.0029(8) C11 0.0211(11) 0.0201(10) 0.0249(11) 0.0002(8) 0.0003(8) -0.0005(8) C12 0.0263(11) 0.0199(10) 0.0240(11) -0.0027(8) -0.0004(8) 0.0001(8) C13 0.0234(11) 0.0227(10) 0.0223(11) 0.0002(8) 0.0017(8) 0.0019(8) S14 0.0335(3) 0.0213(3) 0.0269(3) 0.0038(2) -0.0056(2) -0.0009(2) O1 0.0441(9) 0.0328(8) 0.0262(8) 0.0058(6) -0.0129(6) -0.0035(7) O2 0.0349(9) 0.0216(7) 0.0424(9) -0.0017(6) -0.0020(7) 0.0050(6) C15 0.0335(12) 0.0190(10) 0.0210(10) 0.0051(8) -0.0019(9) -0.0043(9) C16 0.0436(14) 0.0231(11) 0.0196(11) 0.0003(8) -0.0039(9) -0.0080(10) C17 0.0429(13) 0.0241(11) 0.0208(11) -0.0013(8) 0.0051(9) -0.0066(10) C18 0.0344(12) 0.0191(10) 0.0210(11) 0.0039(8) 0.0023(9) -0.0033(9) C19 0.0363(13) 0.0185(10) 0.0186(10) -0.0012(8) -0.0002(9) -0.0032(9) C20 0.0354(13) 0.0202(10) 0.0232(11) 0.0039(8) 0.0026(9) -0.0007(9) N21 0.0352(11) 0.0287(9) 0.0250(9) -0.0086(8) 0.0059(8) -0.0060(8) C22 0.0414(13) 0.0228(11) 0.0210(11) 0.0020(9) 0.0075(9) -0.0016(9) N23 0.0549(13) 0.0319(10) 0.0299(10) -0.0067(8) 0.0194(9) -0.0112(9) C24 0.0678(18) 0.0394(13) 0.0351(14) -0.0101(11) 0.0263(12) -0.0141(12) C25 0.0572(17) 0.0358(13) 0.0407(14) -0.0004(11) 0.0271(12) -0.0030(12) C26 0.0428(15) 0.0340(12) 0.0352(13) 0.0050(10) 0.0106(11) -0.0003(11) C27 0.0406(14) 0.0279(11) 0.0269(12) -0.0023(9) 0.0071(10) -0.0015(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 N1A C2A 1.344(2) . ? N1A C14A 1.346(2) . ? C2A C3A 1.417(3) . ? C2A C7A 1.427(3) . ? C3A C4A 1.362(3) . ? C3A H3AA 0.9601 . ? C4A C5A 1.417(3) . ? C4A H4AA 0.9600 . ? C5A C6A 1.346(3) . ? C5A H5AA 0.9602 . ? C6A C7A 1.421(3) . ? C6A H6AA 0.9600 . ? C7A N8A 1.348(2) . ? N8A C9A 1.345(2) . ? C9A C10A 1.416(3) . ? C9A C14A 1.426(3) . ? C10A C11A 1.356(3) . ? C10A H10A 0.9600 . ? C11A C12A 1.410(3) . ? C11A H11A 0.9600 . ? C12A C13A 1.350(3) . ? C12A H12A 0.9599 . ? C13A C14A 1.427(3) . ? C13A H13A 0.9600 . ? N1 C2 1.331(2) . ? N1 C6 1.338(2) . ? C2 N7 1.386(2) . ? C2 C3 1.406(3) . ? C3 C4 1.369(3) . ? C3 H3A 0.9601 . ? C4 C5 1.385(3) . ? C4 H4A 0.9600 . ? C5 C6 1.369(3) . ? C5 H5A 0.9601 . ? C6 H6A 0.9600 . ? N7 C8 1.389(2) . ? N7 H7A 0.9001 . ? C8 C9 1.398(2) . ? C8 C13 1.400(2) . ? C9 C10 1.375(2) . ? C9 H9A 0.9599 . ? C10 C11 1.394(2) . ? C10 H10B 0.9599 . ? C11 C12 1.389(2) . ? C11 S14 1.7541(18) . ? C12 C13 1.376(2) . ? C12 H12B 0.9600 . ? C13 H13B 0.9600 . ? S14 O1 1.4357(13) . ? S14 O2 1.4463(14) . ? S14 C15 1.751(2) . ? C15 C16 1.387(3) . ? C15 C20 1.396(3) . ? C16 C17 1.377(3) . ? C16 H16A 0.9598 . ? C17 C18 1.405(3) . ? C17 H17A 0.9600 . ? C18 N21 1.387(2) . ? C18 C19 1.405(3) . ? C19 C20 1.375(3) . ? C19 H19A 0.9600 . ? C20 H20A 0.9600 . ? N21 C22 1.390(2) . ? N21 H21A 0.9001 . ? C22 N23 1.330(2) . ? C22 C27 1.402(3) . ? N23 C24 1.347(3) . ? C24 C25 1.365(3) . ? C24 H24A 0.9601 . ? C25 C26 1.390(3) . ? C25 H25A 0.9600 . ? C26 C27 1.374(3) . ? C26 H26A 0.9600 . ? C27 H27A 0.9601 . ? 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 C2A N1A C14A 117.38(16) . . ? N1A C2A C3A 119.68(18) . . ? N1A C2A C7A 121.20(17) . . ? C3A C2A C7A 119.11(18) . . ? C4A C3A C2A 120.0(2) . . ? C4A C3A H3AA 119.9 . . ? C2A C3A H3AA 120.1 . . ? C3A C4A C5A 120.7(2) . . ? C3A C4A H4AA 119.7 . . ? C5A C4A H4AA 119.7 . . ? C6A C5A C4A 120.9(2) . . ? C6A C5A H5AA 119.5 . . ? C4A C5A H5AA 119.6 . . ? C5A C6A C7A 120.4(2) . . ? C5A C6A H6AA 119.8 . . ? C7A C6A H6AA 119.8 . . ? N8A C7A C6A 119.50(19) . . ? N8A C7A C2A 121.63(18) . . ? C6A C7A C2A 118.87(19) . . ? C9A N8A C7A 116.86(17) . . ? N8A C9A C10A 119.78(19) . . ? N8A C9A C14A 121.65(17) . . ? C10A C9A C14A 118.58(19) . . ? C11A C10A C9A 120.1(2) . . ? C11A C10A H10A 119.8 . . ? C9A C10A H10A 120.0 . . ? C10A C11A C12A 121.3(2) . . ? C10A C11A H11A 119.4 . . ? C12A C11A H11A 119.3 . . ? C13A C12A C11A 120.7(2) . . ? C13A C12A H12A 119.6 . . ? C11A C12A H12A 119.7 . . ? C12A C13A C14A 119.8(2) . . ? C12A C13A H13A 120.2 . . ? C14A C13A H13A 120.0 . . ? N1A C14A C9A 121.24(17) . . ? N1A C14A C13A 119.35(18) . . ? C9A C14A C13A 119.41(18) . . ? C2 N1 C6 116.91(16) . . ? N1 C2 N7 120.12(16) . . ? N1 C2 C3 122.67(18) . . ? N7 C2 C3 117.21(17) . . ? C4 C3 C2 118.3(2) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 120.7 . . ? C3 C4 C5 119.77(19) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.2 . . ? C6 C5 C4 117.42(19) . . ? C6 C5 H5A 121.4 . . ? C4 C5 H5A 121.2 . . ? N1 C6 C5 124.9(2) . . ? N1 C6 H6A 117.6 . . ? C5 C6 H6A 117.5 . . ? C2 N7 C8 131.72(16) . . ? C2 N7 H7A 114.1 . . ? C8 N7 H7A 114.1 . . ? N7 C8 C9 116.08(16) . . ? N7 C8 C13 124.67(16) . . ? C9 C8 C13 119.25(16) . . ? C10 C9 C8 121.35(17) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C11 119.02(17) . . ? C9 C10 H10B 120.5 . . ? C11 C10 H10B 120.4 . . ? C12 C11 C10 119.96(16) . . ? C12 C11 S14 120.98(14) . . ? C10 C11 S14 119.06(14) . . ? C13 C12 C11 121.16(17) . . ? C13 C12 H12B 119.5 . . ? C11 C12 H12B 119.4 . . ? C12 C13 C8 119.23(17) . . ? C12 C13 H13B 120.4 . . ? C8 C13 H13B 120.3 . . ? O1 S14 O2 118.71(8) . . ? O1 S14 C15 108.06(9) . . ? O2 S14 C15 107.60(8) . . ? O1 S14 C11 108.06(8) . . ? O2 S14 C11 108.14(8) . . ? C15 S14 C11 105.51(9) . . ? C16 C15 C20 119.26(19) . . ? C16 C15 S14 119.82(15) . . ? C20 C15 S14 120.81(16) . . ? C17 C16 C15 121.57(18) . . ? C17 C16 H16A 119.2 . . ? C15 C16 H16A 119.2 . . ? C16 C17 C18 119.61(19) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? N21 C18 C19 116.05(17) . . ? N21 C18 C17 125.46(18) . . ? C19 C18 C17 118.49(19) . . ? C20 C19 C18 121.33(18) . . ? C20 C19 H19A 119.3 . . ? C18 C19 H19A 119.4 . . ? C19 C20 C15 119.73(19) . . ? C19 C20 H20A 120.2 . . ? C15 C20 H20A 120.1 . . ? C18 N21 C22 131.53(17) . . ? C18 N21 H21A 114.3 . . ? C22 N21 H21A 114.2 . . ? N23 C22 N21 119.26(18) . . ? N23 C22 C27 123.26(18) . . ? N21 C22 C27 117.47(17) . . ? C22 N23 C24 116.08(19) . . ? N23 C24 C25 125.1(2) . . ? N23 C24 H24A 117.6 . . ? C25 C24 H24A 117.3 . . ? C24 C25 C26 118.0(2) . . ? C24 C25 H25A 121.0 . . ? C26 C25 H25A 121.0 . . ? C27 C26 C25 118.7(2) . . ? C27 C26 H26A 120.8 . . ? C25 C26 H26A 120.5 . . ? C26 C27 C22 118.82(19) . . ? C26 C27 H27A 120.5 . . ? C22 C27 H27A 120.7 . . ? 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 C14A N1A C2A C3A 179.31(17) . . . . ? C14A N1A C2A C7A -0.3(3) . . . . ? N1A C2A C3A C4A 179.73(18) . . . . ? C7A C2A C3A C4A -0.7(3) . . . . ? C2A C3A C4A C5A -0.4(3) . . . . ? C3A C4A C5A C6A 0.6(3) . . . . ? C4A C5A C6A C7A 0.4(3) . . . . ? C5A C6A C7A N8A 178.45(19) . . . . ? C5A C6A C7A C2A -1.4(3) . . . . ? N1A C2A C7A N8A 1.3(3) . . . . ? C3A C2A C7A N8A -178.30(17) . . . . ? N1A C2A C7A C6A -178.84(17) . . . . ? C3A C2A C7A C6A 1.6(3) . . . . ? C6A C7A N8A C9A 179.57(17) . . . . ? C2A C7A N8A C9A -0.6(3) . . . . ? C7A N8A C9A C10A 178.65(18) . . . . ? C7A N8A C9A C14A -1.1(3) . . . . ? N8A C9A C10A C11A 178.97(19) . . . . ? C14A C9A C10A C11A -1.3(3) . . . . ? C9A C10A C11A C12A -0.4(3) . . . . ? C10A C11A C12A C13A 1.0(3) . . . . ? C11A C12A C13A C14A 0.1(3) . . . . ? C2A N1A C14A C9A -1.3(3) . . . . ? C2A N1A C14A C13A 178.67(17) . . . . ? N8A C9A C14A N1A 2.1(3) . . . . ? C10A C9A C14A N1A -177.61(17) . . . . ? N8A C9A C14A C13A -177.91(17) . . . . ? C10A C9A C14A C13A 2.4(3) . . . . ? C12A C13A C14A N1A 178.19(18) . . . . ? C12A C13A C14A C9A -1.8(3) . . . . ? C6 N1 C2 N7 179.35(16) . . . . ? C6 N1 C2 C3 -0.9(3) . . . . ? N1 C2 C3 C4 0.2(3) . . . . ? N7 C2 C3 C4 179.95(17) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C2 N1 C6 C5 1.0(3) . . . . ? C4 C5 C6 N1 -0.4(3) . . . . ? N1 C2 N7 C8 7.6(3) . . . . ? C3 C2 N7 C8 -172.12(17) . . . . ? C2 N7 C8 C9 175.26(18) . . . . ? C2 N7 C8 C13 -4.0(3) . . . . ? N7 C8 C9 C10 -178.06(16) . . . . ? C13 C8 C9 C10 1.3(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 -1.3(3) . . . . ? C9 C10 C11 S14 178.90(14) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? S14 C11 C12 C13 -178.64(14) . . . . ? C11 C12 C13 C8 -0.4(3) . . . . ? N7 C8 C13 C12 178.25(17) . . . . ? C9 C8 C13 C12 -1.0(3) . . . . ? C12 C11 S14 O1 171.97(15) . . . . ? C10 C11 S14 O1 -8.25(18) . . . . ? C12 C11 S14 O2 42.29(17) . . . . ? C10 C11 S14 O2 -137.94(15) . . . . ? C12 C11 S14 C15 -72.62(17) . . . . ? C10 C11 S14 C15 107.15(16) . . . . ? O1 S14 C15 C16 32.84(17) . . . . ? O2 S14 C15 C16 162.15(14) . . . . ? C11 S14 C15 C16 -82.57(16) . . . . ? O1 S14 C15 C20 -150.76(14) . . . . ? O2 S14 C15 C20 -21.45(17) . . . . ? C11 S14 C15 C20 93.83(16) . . . . ? C20 C15 C16 C17 0.1(3) . . . . ? S14 C15 C16 C17 176.53(14) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 N21 179.38(17) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? N21 C18 C19 C20 -179.44(16) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C15 0.1(3) . . . . ? C16 C15 C20 C19 0.0(3) . . . . ? S14 C15 C20 C19 -176.47(13) . . . . ? C19 C18 N21 C22 -178.38(18) . . . . ? C17 C18 N21 C22 2.4(3) . . . . ? C18 N21 C22 N23 3.7(3) . . . . ? C18 N21 C22 C27 -177.35(18) . . . . ? N21 C22 N23 C24 177.99(18) . . . . ? C27 C22 N23 C24 -0.9(3) . . . . ? C22 N23 C24 C25 0.5(3) . . . . ? N23 C24 C25 C26 0.0(3) . . . . ? C24 C25 C26 C27 -0.1(3) . . . . ? C25 C26 C27 C22 -0.2(3) . . . . ? N23 C22 C27 C26 0.8(3) . . . . ? N21 C22 C27 C26 -178.12(17) . . . . ? 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 N7 H7A O2 0.90 2.15 3.027(2) 165.8 1_565 N21 H21A N1A 0.90 2.08 2.980(2) 175.9 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.236 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.053 _chemical_name_common ;N,N'-Bis(2-pyridyl)-4,4'-sulphonyldianiline phenazine 1:1 complex ; #===END data_4-phz _database_code_depnum_ccdc_archive 'CCDC 198840' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,3-diamino-2-methylbenzene phenazine 2:1 ; _chemical_melting_point 165-166 _chemical_formula_moiety 'C17 H16 N4, 0.5(C12 H8 N2)' _chemical_formula_sum 'C23 H20 N5' _chemical_formula_weight 366.44 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 -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5174(7) _cell_length_b 8.6054(9) _cell_length_c 14.5408(11) _cell_angle_alpha 99.694(7) _cell_angle_beta 93.711(6) _cell_angle_gamma 115.471(9) _cell_volume 937.12(17) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 4828 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 386 _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 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% negligible _diffrn_reflns_number 7115 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3309 _reflns_number_gt 2469 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation, Siemens Analytical X-Ray Instruments, Inc., 1989. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap,geom _refine_ls_hydrogen_treatment refu _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3309 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 N1 N 0.10925(17) 0.31351(16) 0.22165(9) 0.0252(3) Uani 1 1 d . . . C2 C 0.10533(19) 0.4646(2) 0.21409(11) 0.0234(4) Uani 1 1 d . . . C3 C 0.0937(2) 0.5800(2) 0.29163(11) 0.0249(4) Uani 1 1 d . . . H3 H 0.0854 0.6841 0.2821 0.027(4) Uiso 1 1 d R . . C4 C 0.0863(2) 0.5351(2) 0.37774(12) 0.0282(4) Uani 1 1 d . . . H4 H 0.0790 0.6137 0.4307 0.030(4) Uiso 1 1 d R . . C5 C 0.0897(2) 0.3783(2) 0.38677(11) 0.0286(4) Uani 1 1 d . . . H5 H 0.0927 0.3465 0.4468 0.034(5) Uiso 1 1 d R . . C6 C 0.1007(2) 0.2744(2) 0.30763(11) 0.0272(4) Uani 1 1 d . . . H6 H 0.1072 0.1666 0.3103 0.023(4) Uiso 1 1 d R . . N7 N 0.11283(17) 0.50693(17) 0.12731(9) 0.0265(3) Uani 1 1 d . . . H7 H 0.1538 0.6230 0.1293 0.056(6) Uiso 1 1 d R . . C8 C 0.1101(2) 0.3952(2) 0.04296(11) 0.0238(4) Uani 1 1 d . . . C9 C -0.0381(2) 0.2347(2) 0.00534(11) 0.0229(4) Uani 1 1 d . . . C10 C -0.0336(2) 0.1345(2) -0.07993(11) 0.0236(4) Uani 1 1 d . . . C11 C 0.1121(2) 0.1933(2) -0.12696(12) 0.0293(4) Uani 1 1 d . . . H11 H 0.1120 0.1229 -0.1857 0.020(4) Uiso 1 1 d R . . C12 C 0.2553(2) 0.3533(2) -0.08923(12) 0.0317(4) Uani 1 1 d . . . H12 H 0.3553 0.3923 -0.1217 0.043(5) Uiso 1 1 d R . . C13 C 0.2548(2) 0.4539(2) -0.00475(12) 0.0287(4) Uani 1 1 d . . . H13 H 0.3542 0.5649 0.0228 0.028(4) Uiso 1 1 d R . . N14 N -0.18041(17) -0.03088(17) -0.12079(9) 0.0267(3) Uani 1 1 d . . . H14 H -0.1592 -0.1252 -0.1358 0.039(5) Uiso 1 1 d R . . C15 C -0.3283(2) -0.0429(2) -0.17172(11) 0.0241(4) Uani 1 1 d . . . N16 N -0.33814(17) 0.10746(16) -0.17482(9) 0.0269(3) Uani 1 1 d . . . C17 C -0.4830(2) 0.0948(2) -0.22564(12) 0.0304(4) Uani 1 1 d . . . H17 H -0.4860 0.2047 -0.2270 0.033(5) Uiso 1 1 d R . . C18 C -0.6191(2) -0.0600(2) -0.27377(12) 0.0332(4) Uani 1 1 d . . . H18 H -0.7160 -0.0568 -0.3096 0.033(5) Uiso 1 1 d R . . C19 C -0.6092(2) -0.2154(2) -0.26848(13) 0.0348(4) Uani 1 1 d . . . H19 H -0.7023 -0.3277 -0.3006 0.043(5) Uiso 1 1 d R . . C20 C -0.4642(2) -0.2083(2) -0.21748(12) 0.0299(4) Uani 1 1 d . . . H20 H -0.4507 -0.3123 -0.2137 0.028(4) Uiso 1 1 d R . . C21 C -0.1978(2) 0.1719(2) 0.05313(12) 0.0291(4) Uani 1 1 d . . . H21A H -0.2009 0.0863 0.0885 0.071(7) Uiso 1 1 d R . . H21B H -0.3044 0.1085 0.0085 0.043(5) Uiso 1 1 d R . . H21C H -0.1986 0.2683 0.0970 0.038(5) Uiso 1 1 d R . . N1A N 1.02852(17) 0.91140(17) 0.41589(9) 0.0283(4) Uani 1 1 d . . . C2A C 0.8662(2) 0.8631(2) 0.43882(11) 0.0249(4) Uani 1 1 d . . . C3A C 0.7203(2) 0.7187(2) 0.37938(12) 0.0321(4) Uani 1 1 d . . . H3A H 0.7461 0.6653 0.3227 0.026(4) Uiso 1 1 d R . . C4A C 0.5560(2) 0.6655(2) 0.40352(13) 0.0384(5) Uani 1 1 d . . . H4A H 0.4588 0.5644 0.3642 0.046(5) Uiso 1 1 d R . . C5A C 0.5288(2) 0.7561(3) 0.48715(13) 0.0424(5) Uani 1 1 d . . . H5A H 0.4123 0.7121 0.5034 0.060(6) Uiso 1 1 d R . . C6A C 0.6635(2) 0.8956(2) 0.54519(13) 0.0359(4) Uani 1 1 d . . . H6A H 0.6467 0.9554 0.6028 0.041(5) Uiso 1 1 d R . . C7A C 0.8381(2) 0.9538(2) 0.52376(11) 0.0271(4) 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 N1 0.0275(7) 0.0230(7) 0.0256(7) 0.0035(6) 0.0011(6) 0.0130(6) C2 0.0204(8) 0.0235(8) 0.0244(9) 0.0028(7) -0.0008(7) 0.0094(7) C3 0.0234(8) 0.0254(9) 0.0273(9) 0.0023(7) 0.0028(7) 0.0135(7) C4 0.0243(9) 0.0333(10) 0.0259(9) 0.0001(7) 0.0049(7) 0.0142(8) C5 0.0290(9) 0.0348(10) 0.0245(9) 0.0080(8) 0.0055(7) 0.0159(8) C6 0.0271(9) 0.0281(9) 0.0279(9) 0.0076(7) 0.0025(7) 0.0135(8) N7 0.0365(8) 0.0216(8) 0.0218(7) 0.0019(6) 0.0004(6) 0.0150(7) C8 0.0277(9) 0.0243(9) 0.0227(9) 0.0030(7) 0.0001(7) 0.0161(8) C9 0.0254(9) 0.0251(9) 0.0232(9) 0.0059(7) 0.0011(7) 0.0161(7) C10 0.0263(9) 0.0224(9) 0.0240(9) 0.0021(7) -0.0008(7) 0.0145(7) C11 0.0324(10) 0.0331(10) 0.0247(9) -0.0002(8) 0.0035(7) 0.0193(8) C12 0.0285(9) 0.0386(10) 0.0317(10) 0.0076(8) 0.0091(8) 0.0176(9) C13 0.0267(9) 0.0273(9) 0.0293(10) 0.0038(8) -0.0018(7) 0.0114(8) N14 0.0299(8) 0.0216(7) 0.0292(8) 0.0006(6) -0.0004(6) 0.0145(6) C15 0.0253(9) 0.0261(9) 0.0222(8) 0.0047(7) 0.0074(7) 0.0124(7) N16 0.0261(7) 0.0257(8) 0.0298(8) 0.0052(6) 0.0028(6) 0.0129(6) C17 0.0283(9) 0.0336(10) 0.0329(10) 0.0085(8) 0.0054(8) 0.0165(8) C18 0.0241(9) 0.0433(11) 0.0320(10) 0.0068(8) 0.0034(7) 0.0155(8) C19 0.0242(9) 0.0328(10) 0.0378(11) 0.0019(8) 0.0061(8) 0.0058(8) C20 0.0284(9) 0.0257(9) 0.0328(10) 0.0036(8) 0.0063(7) 0.0104(8) C21 0.0302(9) 0.0283(9) 0.0283(9) 0.0048(8) 0.0031(8) 0.0134(8) N1A 0.0307(8) 0.0293(8) 0.0283(8) 0.0062(6) 0.0040(6) 0.0166(7) C2A 0.0283(9) 0.0263(9) 0.0252(9) 0.0082(7) 0.0046(7) 0.0159(8) C3A 0.0349(10) 0.0326(10) 0.0282(10) 0.0023(8) 0.0021(8) 0.0165(9) C4A 0.0305(10) 0.0401(11) 0.0348(11) 0.0026(9) -0.0019(8) 0.0099(9) C5A 0.0266(10) 0.0539(12) 0.0403(12) 0.0077(10) 0.0058(9) 0.0131(10) C6A 0.0323(10) 0.0450(11) 0.0312(10) 0.0046(9) 0.0077(8) 0.0191(9) C7A 0.0290(9) 0.0281(9) 0.0278(9) 0.0063(7) 0.0031(7) 0.0162(8) _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 N1 C2 1.3373(19) . ? N1 C6 1.347(2) . ? C2 N7 1.369(2) . ? C2 C3 1.411(2) . ? C3 C4 1.369(2) . ? C3 H3 0.9600 . ? C4 C5 1.389(2) . ? C4 H4 0.9599 . ? C5 C6 1.368(2) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.4176(19) . ? N7 H7 0.9000 . ? C8 C13 1.396(2) . ? C8 C9 1.399(2) . ? C9 C10 1.399(2) . ? C9 C21 1.498(2) . ? C10 C11 1.397(2) . ? C10 N14 1.4247(19) . ? C11 C12 1.378(2) . ? C11 H11 0.9600 . ? C12 C13 1.380(2) . ? C12 H12 0.9599 . ? C13 H13 0.9600 . ? N14 C15 1.3741(19) . ? N14 H14 0.9001 . ? C15 N16 1.3397(19) . ? C15 C20 1.405(2) . ? N16 C17 1.349(2) . ? C17 C18 1.364(2) . ? C17 H17 0.9600 . ? C18 C19 1.391(2) . ? C18 H18 0.9600 . ? C19 C20 1.371(2) . ? C19 H19 0.9600 . ? C20 H20 0.9599 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1A C7A 1.342(2) 2_776 ? N1A C2A 1.344(2) . ? C2A C3A 1.417(2) . ? C2A C7A 1.438(2) . ? C3A C4A 1.363(2) . ? C3A H3A 0.9600 . ? C4A C5A 1.418(3) . ? C4A H4A 0.9600 . ? C5A C6A 1.349(3) . ? C5A H5A 0.9600 . ? C6A C7A 1.425(2) . ? C6A H6A 0.9600 . ? C7A N1A 1.342(2) 2_776 ? 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 N1 C6 116.88(13) . . ? N1 C2 N7 118.04(14) . . ? N1 C2 C3 122.50(14) . . ? N7 C2 C3 119.46(13) . . ? C4 C3 C2 118.49(14) . . ? C4 C3 H3 122.0 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.75(15) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 121.6 . . ? C6 C5 C4 117.68(15) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 121.9 . . ? N1 C6 C5 124.70(14) . . ? N1 C6 H6 114.2 . . ? C5 C6 H6 121.1 . . ? C2 N7 C8 124.53(13) . . ? C2 N7 H7 114.3 . . ? C8 N7 H7 118.7 . . ? C13 C8 C9 120.64(15) . . ? C13 C8 N7 118.37(14) . . ? C9 C8 N7 120.89(14) . . ? C10 C9 C8 117.66(14) . . ? C10 C9 C21 120.60(15) . . ? C8 C9 C21 121.74(14) . . ? C11 C10 C9 121.42(15) . . ? C11 C10 N14 118.67(14) . . ? C9 C10 N14 119.91(14) . . ? C12 C11 C10 119.80(15) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 119.89(16) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 120.8 . . ? C12 C13 C8 120.57(15) . . ? C12 C13 H13 120.8 . . ? C8 C13 H13 118.6 . . ? C15 N14 C10 122.08(13) . . ? C15 N14 H14 115.3 . . ? C10 N14 H14 117.3 . . ? N16 C15 N14 117.68(14) . . ? N16 C15 C20 121.93(14) . . ? N14 C15 C20 120.38(14) . . ? C15 N16 C17 117.37(14) . . ? N16 C17 C18 124.47(15) . . ? N16 C17 H17 115.5 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 117.67(16) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 123.3 . . ? C20 C19 C18 119.67(16) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 120.8 . . ? C19 C20 C15 118.87(15) . . ? C19 C20 H20 122.2 . . ? C15 C20 H20 118.9 . . ? C9 C21 H21A 111.8 . . ? C9 C21 H21B 111.9 . . ? H21A C21 H21B 102.9 . . ? C9 C21 H21C 110.6 . . ? H21A C21 H21C 106.8 . . ? H21B C21 H21C 112.5 . . ? C7A N1A C2A 116.93(14) 2_776 . ? N1A C2A C3A 119.72(15) . . ? N1A C2A C7A 121.10(15) . . ? C3A C2A C7A 119.18(15) . . ? C4A C3A C2A 120.10(16) . . ? C4A C3A H3A 124.2 . . ? C2A C3A H3A 115.7 . . ? C3A C4A C5A 120.49(17) . . ? C3A C4A H4A 119.5 . . ? C5A C4A H4A 120.0 . . ? C6A C5A C4A 121.41(17) . . ? C6A C5A H5A 120.3 . . ? C4A C5A H5A 118.3 . . ? C5A C6A C7A 120.09(17) . . ? C5A C6A H6A 121.9 . . ? C7A C6A H6A 118.0 . . ? N1A C7A C6A 119.30(15) 2_776 . ? N1A C7A C2A 121.97(15) 2_776 . ? C6A C7A C2A 118.71(16) . . ? 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 N7 H7 N16 0.90 2.12 2.9581(19) 154.4 2_565 N14 H14 N1 0.90 2.09 2.9351(18) 157.1 2 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.252 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.055 _chemical_name_common "N,N'-Bis(2-pyridyl)-1,3-diamino-2-methylbenzene phenazine 2:1" #===END data_6-phz _database_code_depnum_ccdc_archive 'CCDC 198841' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Diphenyl-1,4-diaminobenzene phenazine 1:1 complex ; _chemical_melting_point 128 _chemical_formula_moiety 'C18 H16 N2, C12 H8 N2' _chemical_formula_sum 'C30 H24 N4' _chemical_formula_weight 440.53 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 -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3360(8) _cell_length_b 10.8324(17) _cell_length_c 11.4215(17) _cell_angle_alpha 66.689(15) _cell_angle_beta 78.508(12) _cell_angle_gamma 81.096(13) _cell_volume 592.02(16) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5984 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour dark-brown _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% negligible _diffrn_reflns_number 4417 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2096 _reflns_number_gt 1570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.157a, 1999' _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation, Siemens Analytical X-Ray Instruments, Inc., 1989. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0563P)^2^+0.2296P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap,geom _refine_ls_hydrogen_treatment refu _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.067(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2096 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 C1A C -0.0267(5) 0.7982(3) 0.6917(3) 0.0711(7) Uani 1 1 d . . . H1A H -0.1500 0.7324 0.7215 0.080(8) Uiso 1 1 d R . . C2A C 0.1475(4) 0.8073(2) 0.5857(2) 0.0636(6) Uani 1 1 d . . . H2A H 0.1579 0.7503 0.5381 0.079(8) Uiso 1 1 d R . . C3A C 0.3313(4) 0.9046(2) 0.5394(2) 0.0521(5) Uani 1 1 d . . . N4A N 0.5063(3) 0.91297(17) 0.43408(18) 0.0547(5) Uani 1 1 d . . . C5A C 0.6749(4) 1.0066(2) 0.3945(2) 0.0516(5) Uani 1 1 d . . . C6A C 0.8631(5) 1.0191(2) 0.2847(2) 0.0637(6) Uani 1 1 d . . . H6A H 0.8649 0.9581 0.2422 0.080(8) Uiso 1 1 d R . . C7A C 1.0324(5) 1.1146(3) 0.2427(3) 0.0716(7) Uani 1 1 d . . . H7A H 1.1583 1.1251 0.1673 0.084(8) Uiso 1 1 d R . . C1 C 0.6386(4) 0.7003(2) 0.2117(2) 0.0510(5) Uani 1 1 d . . . C2 C 0.4687(5) 0.8067(2) 0.1484(2) 0.0640(6) Uani 1 1 d . . . H2 H 0.4071 0.8721 0.1870 0.067(7) Uiso 1 1 d R . . C3 C 0.3800(5) 0.8111(3) 0.0423(3) 0.0757(8) Uani 1 1 d . . . H3 H 0.2564 0.8834 0.0043 0.095(9) Uiso 1 1 d R . . C4 C 0.4598(5) 0.7118(3) -0.0075(3) 0.0769(8) Uani 1 1 d . . . H4 H 0.4006 0.7205 -0.0846 0.084(8) Uiso 1 1 d R . . C5 C 0.6333(5) 0.6088(3) 0.0518(3) 0.0709(7) Uani 1 1 d . . . H5 H 0.6978 0.5385 0.0197 0.077(8) Uiso 1 1 d R . . C6 C 0.7223(4) 0.6011(2) 0.1608(2) 0.0614(6) Uani 1 1 d . . . H6 H 0.8632 0.5336 0.1826 0.078(8) Uiso 1 1 d R . . N7 N 0.7074(4) 0.69803(18) 0.32328(19) 0.0614(5) Uani 1 1 d . . . H7 H 0.6097 0.7570 0.3545 0.075(8) Uiso 1 1 d R . . C8 C 0.8552(4) 0.5963(2) 0.4094(2) 0.0508(5) Uani 1 1 d . . . C9 C 1.0898(4) 0.5391(2) 0.3692(2) 0.0538(6) Uani 1 1 d . . . H9 H 1.1627 0.5665 0.2797 0.060(6) Uiso 1 1 d R . . C10 C 0.7673(4) 0.5556(2) 0.5413(2) 0.0552(6) Uani 1 1 d . . . H10 H 0.6017 0.5907 0.5713 0.062(6) Uiso 1 1 d 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 C1A 0.0602(14) 0.0595(14) 0.0855(18) -0.0200(13) -0.0070(13) -0.0070(12) C2A 0.0616(14) 0.0544(13) 0.0785(16) -0.0279(12) -0.0158(12) -0.0010(11) C3A 0.0525(12) 0.0443(11) 0.0613(13) -0.0209(10) -0.0164(10) 0.0036(9) N4A 0.0569(11) 0.0507(10) 0.0627(11) -0.0275(9) -0.0151(9) 0.0027(8) C5A 0.0528(12) 0.0459(11) 0.0581(13) -0.0215(10) -0.0158(10) 0.0053(9) C6A 0.0672(15) 0.0622(14) 0.0619(14) -0.0268(12) -0.0072(12) -0.0006(12) C7A 0.0669(15) 0.0686(16) 0.0682(16) -0.0200(13) -0.0014(13) -0.0013(13) C1 0.0513(12) 0.0462(11) 0.0565(12) -0.0187(10) -0.0097(10) -0.0067(9) C2 0.0691(15) 0.0536(13) 0.0679(15) -0.0206(12) -0.0174(12) 0.0015(11) C3 0.0784(17) 0.0710(17) 0.0701(17) -0.0137(14) -0.0263(14) -0.0007(14) C4 0.0832(18) 0.0862(19) 0.0620(16) -0.0209(14) -0.0228(14) -0.0134(15) C5 0.0715(16) 0.0789(17) 0.0748(17) -0.0396(14) -0.0152(13) -0.0076(13) C6 0.0567(13) 0.0610(14) 0.0737(16) -0.0315(12) -0.0162(11) -0.0007(11) N7 0.0721(12) 0.0525(11) 0.0688(12) -0.0324(10) -0.0254(10) 0.0135(9) C8 0.0502(12) 0.0462(11) 0.0636(13) -0.0254(10) -0.0157(10) -0.0039(9) C9 0.0478(12) 0.0589(13) 0.0587(13) -0.0257(11) -0.0064(10) -0.0083(10) C10 0.0456(12) 0.0590(13) 0.0674(14) -0.0317(11) -0.0089(10) -0.0006(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 C1A C2A 1.351(3) . ? C1A C7A 1.412(4) 2_676 ? C1A H1A 0.9600 . ? C2A C3A 1.423(3) . ? C2A H2A 0.9599 . ? C3A N4A 1.349(3) . ? C3A C5A 1.432(3) 2_676 ? N4A C5A 1.342(3) . ? C5A C6A 1.416(3) . ? C6A C7A 1.357(4) . ? C6A H6A 0.9601 . ? C7A H7A 0.9600 . ? C1 N7 1.385(3) . ? C1 C6 1.392(3) . ? C1 C2 1.397(3) . ? C2 C3 1.368(3) . ? C2 H2 0.9599 . ? C3 C4 1.380(4) . ? C3 H3 0.9600 . ? C4 C5 1.376(4) . ? C4 H4 0.9600 . ? C5 C6 1.387(3) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.409(3) . ? N7 H7 0.8999 . ? C8 C9 1.385(3) . ? C8 C10 1.392(3) . ? C9 C10 1.384(3) 2_766 ? C9 H9 0.9600 . ? C10 C9 1.384(3) 2_766 ? C10 H10 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 C2A C1A C7A 121.0(2) . 2_676 ? C2A C1A H1A 119.0 . . ? C7A C1A H1A 119.9 2_676 . ? C1A C2A C3A 120.0(2) . . ? C1A C2A H2A 123.8 . . ? C3A C2A H2A 116.2 . . ? N4A C3A C2A 120.0(2) . . ? N4A C3A C5A 121.02(19) . 2_676 ? C2A C3A C5A 119.0(2) . 2_676 ? C5A N4A C3A 117.51(18) . . ? N4A C5A C6A 119.7(2) . . ? N4A C5A C3A 121.5(2) . 2_676 ? C6A C5A C3A 118.9(2) . 2_676 ? C7A C6A C5A 120.2(2) . . ? C7A C6A H6A 122.2 . . ? C5A C6A H6A 117.6 . . ? C6A C7A C1A 120.9(2) . 2_676 ? C6A C7A H7A 120.8 . . ? C1A C7A H7A 118.3 2_676 . ? N7 C1 C6 124.0(2) . . ? N7 C1 C2 118.0(2) . . ? C6 C1 C2 117.9(2) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 H2 121.9 . . ? C1 C2 H2 116.7 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.2(2) . . ? C5 C4 H4 122.8 . . ? C3 C4 H4 118.8 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 116.9 . . ? C5 C6 C1 119.9(2) . . ? C5 C6 H6 112.4 . . ? C1 C6 H6 126.7 . . ? C1 N7 C8 128.40(18) . . ? C1 N7 H7 113.5 . . ? C8 N7 H7 115.7 . . ? C9 C8 C10 118.4(2) . . ? C9 C8 N7 122.9(2) . . ? C10 C8 N7 118.64(19) . . ? C10 C9 C8 120.4(2) 2_766 . ? C10 C9 H9 117.9 2_766 . ? C8 C9 H9 121.7 . . ? C9 C10 C8 121.3(2) 2_766 . ? C9 C10 H10 118.8 2_766 . ? C8 C10 H10 119.9 . . ? 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 N7 H7 N4A 0.90 2.17 3.032(2) 159.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.273 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.042 #===END _chemical_name_common "N,N'-Diphenyl-1,4-diaminobenzene phenazine 1:1 complex"