# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/161 data_global _publ_contact_author_name 'Prof. Dr. Roland Boese' _publ_contact_author_email boese@structchem.uni-essen.de _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Role of weak hydrogen bonds in the crystal structures of phenazine, 5,10-dihydrophenazine and their 1:1 and 3:1 molecular complexes ; # CIF for Compound 2 data_compound-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '5,10-Dihydrophenazine' _chemical_formula_moiety 'C12 H10 N2' _chemical_formula_sum 'C12 H10 N2' _chemical_formula_weight 182.22 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 orhorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.7727(14) _cell_length_b 7.5924(9) _cell_length_c 21.775(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1781.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 ;Nicolet R3m/V four circle diffractometer ; _diffrn_measurement_method 'Wyckoff scan mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2482 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1458 _reflns_number_gt 1217 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SIEMENS SHELXTL-Ver.5.03, 1994' _computing_cell_refinement 'SIEMENS SHELXL-97 UNIX Vers. Release97-1' _computing_data_reduction 'SIEMENS XDISK V.4.20.2 PC' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version Release 97-1' _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 w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.4046P] 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 SHELXL _refine_ls_extinction_coef 0.0058(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1458 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.32438(12) 0.2359(2) 0.85408(6) 0.0238(4) Uani 1 d . . . H1 H 0.2879 0.2686 0.8926 0.029 Uiso 1 d R . . C2 C 0.26554(12) 0.2817(2) 0.79910(6) 0.0218(4) Uani 1 d . . . H2 H 0.1900 0.3488 0.8001 0.026 Uiso 1 d R . . C3 C 0.31539(11) 0.23073(19) 0.74307(6) 0.0188(3) Uani 1 d . . . N4 N 0.25943(10) 0.26956(17) 0.68657(5) 0.0218(3) Uani 1 d . . . H4 H 0.1939 0.3577 0.6883 0.026 Uiso 1 d R . . C5 C 0.33011(12) 0.26668(19) 0.63234(6) 0.0197(3) Uani 1 d . . . C6 C 0.29491(13) 0.3567(2) 0.57978(6) 0.0246(4) Uani 1 d . . . H6 H 0.2211 0.4276 0.5800 0.030 Uiso 1 d R . . C7 C 0.36607(14) 0.3444(2) 0.52652(6) 0.0301(4) Uani 1 d . . . H7 H 0.3411 0.4068 0.4902 0.036 Uiso 1 d R . . C11 C 0.43497(13) 0.1437(2) 0.85307(6) 0.0231(4) Uani 1 d . . . H11 H 0.4763 0.1142 0.8908 0.028 Uiso 1 d R . . C12 C 0.48621(12) 0.0937(2) 0.79685(7) 0.0214(3) Uani 1 d . . . H12 H 0.5637 0.0315 0.7960 0.026 Uiso 1 d R . . C13 C 0.42646(12) 0.13304(19) 0.74225(6) 0.0189(3) Uani 1 d . . . N14 N 0.46765(10) 0.06779(16) 0.68516(5) 0.0218(3) Uani 1 d . . . H14 H 0.5442 0.0094 0.6858 0.026 Uiso 1 d R . . C15 C 0.43882(12) 0.16488(18) 0.63162(6) 0.0196(3) Uani 1 d . . . C16 C 0.50903(13) 0.1541(2) 0.57867(6) 0.0256(4) Uani 1 d . . . H16 H 0.5835 0.0846 0.5783 0.031 Uiso 1 d R . . C17 C 0.47244(14) 0.2433(2) 0.52578(7) 0.0306(4) Uani 1 d . . . H17 H 0.5210 0.2345 0.4889 0.037 Uiso 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 C1 0.0265(7) 0.0219(9) 0.0230(7) -0.0002(6) 0.0044(6) -0.0030(7) C2 0.0179(7) 0.0187(9) 0.0289(7) 0.0006(6) 0.0035(5) -0.0002(6) C3 0.0169(6) 0.0154(8) 0.0241(7) 0.0017(6) 0.0002(5) -0.0039(6) N4 0.0173(5) 0.0251(8) 0.0229(6) 0.0016(5) 0.0007(5) 0.0034(5) C5 0.0198(6) 0.0176(8) 0.0216(7) -0.0049(6) -0.0010(5) -0.0035(6) C6 0.0271(7) 0.0218(9) 0.0250(7) -0.0029(6) -0.0053(6) 0.0031(7) C7 0.0409(9) 0.0290(10) 0.0204(7) -0.0005(7) -0.0026(6) 0.0035(8) C11 0.0245(7) 0.0214(9) 0.0235(7) 0.0022(6) -0.0031(6) -0.0047(6) C12 0.0179(6) 0.0176(8) 0.0287(7) 0.0029(6) -0.0017(5) -0.0022(6) C13 0.0178(6) 0.0155(8) 0.0234(7) 0.0004(6) 0.0030(5) -0.0039(6) N14 0.0192(6) 0.0224(8) 0.0239(6) 0.0000(5) 0.0012(4) 0.0050(5) C15 0.0206(7) 0.0164(8) 0.0219(7) -0.0018(6) -0.0031(5) -0.0032(6) C16 0.0244(7) 0.0246(9) 0.0279(7) -0.0045(6) 0.0019(6) 0.0013(6) C17 0.0370(8) 0.0333(10) 0.0214(7) -0.0033(7) 0.0052(6) 0.0020(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 C1 C11 1.382(2) . ? C1 C2 1.3988(19) . ? C1 H1 0.9600 . ? C2 C3 1.3880(18) . ? C2 H2 0.9600 . ? C3 N4 1.4015(16) . ? C3 C13 1.408(2) . ? N4 C5 1.4053(16) . ? N4 H4 0.9734 . ? C5 C6 1.3859(19) . ? C5 C15 1.4033(19) . ? C6 C7 1.393(2) . ? C6 H6 0.9600 . ? C7 C17 1.379(2) . ? C7 H7 0.9600 . ? C11 C12 1.3955(19) . ? C11 H11 0.9599 . ? C12 C13 1.3845(19) . ? C12 H12 0.9600 . ? C13 N14 1.4098(17) . ? N14 C15 1.4138(17) . ? N14 H14 0.9369 . ? C15 C16 1.3814(18) . ? C16 C17 1.393(2) . ? C16 H16 0.9600 . ? C17 H17 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 C11 C1 C2 120.20(13) . . ? C11 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 120.51(13) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.8 . . ? C2 C3 N4 123.13(12) . . ? C2 C3 C13 119.14(12) . . ? N4 C3 C13 117.72(12) . . ? C3 N4 C5 120.09(11) . . ? C3 N4 H4 115.0 . . ? C5 N4 H4 115.8 . . ? C6 C5 C15 119.39(12) . . ? C6 C5 N4 122.55(12) . . ? C15 C5 N4 118.04(12) . . ? C5 C6 C7 120.25(13) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C17 C7 C6 120.28(14) . . ? C17 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C1 C11 C12 119.51(13) . . ? C1 C11 H11 120.3 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.73(13) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.7 . . ? C12 C13 C3 119.85(12) . . ? C12 C13 N14 122.35(12) . . ? C3 C13 N14 117.64(11) . . ? C13 N14 C15 118.34(11) . . ? C13 N14 H14 115.5 . . ? C15 N14 H14 116.9 . . ? C16 C15 C5 119.93(13) . . ? C16 C15 N14 122.48(12) . . ? C5 C15 N14 117.48(12) . . ? C15 C16 C17 120.41(13) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C7 C17 C16 119.74(13) . . ? C7 C17 H17 120.1 . . ? C16 C17 H17 120.2 . . ? 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 C11 C1 C2 C3 1.9(2) . . . . ? C1 C2 C3 N4 178.66(13) . . . . ? C1 C2 C3 C13 -0.4(2) . . . . ? C2 C3 N4 C5 159.48(13) . . . . ? C13 C3 N4 C5 -21.5(2) . . . . ? C3 N4 C5 C6 -158.09(14) . . . . ? C3 N4 C5 C15 23.4(2) . . . . ? C15 C5 C6 C7 0.8(2) . . . . ? N4 C5 C6 C7 -177.70(14) . . . . ? C5 C6 C7 C17 -0.4(2) . . . . ? C2 C1 C11 C12 -1.2(2) . . . . ? C1 C11 C12 C13 -1.0(2) . . . . ? C11 C12 C13 C3 2.6(2) . . . . ? C11 C12 C13 N14 -172.60(13) . . . . ? C2 C3 C13 C12 -1.9(2) . . . . ? N4 C3 C13 C12 179.02(12) . . . . ? C2 C3 C13 N14 173.55(12) . . . . ? N4 C3 C13 N14 -5.52(19) . . . . ? C12 C13 N14 C15 -154.05(13) . . . . ? C3 C13 N14 C15 30.61(18) . . . . ? C6 C5 C15 C16 -0.5(2) . . . . ? N4 C5 C15 C16 178.04(13) . . . . ? C6 C5 C15 N14 -176.69(12) . . . . ? N4 C5 C15 N14 1.86(18) . . . . ? C13 N14 C15 C16 155.25(13) . . . . ? C13 N14 C15 C5 -28.69(18) . . . . ? C5 C15 C16 C17 -0.2(2) . . . . ? N14 C15 C16 C17 175.80(14) . . . . ? C6 C7 C17 C16 -0.3(2) . . . . ? C15 C16 C17 C7 0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.623 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.623 _refine_diff_density_max 0.181 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.035 # CIF for Complex 3 data_complex-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1:1 molecular complex of phenazine and 5,10-dihydrophenazine ; _chemical_formula_moiety '(C12H8N2). (c12H10N2)' _chemical_formula_sum 'C24 H18 N4' _chemical_formula_weight 362.42 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 monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 11.6466(3) _cell_length_b 6.2335(2) _cell_length_c 12.5573(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.612(2) _cell_angle_gamma 90.00 _cell_volume 903.61(5) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2775 _cell_measurement_theta_min 3 _cell_measurement_theta_max 55 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'Siemens SADABS multi-scan' _exptl_absorpt_correction_T_min 0.715 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 'Siemens SMART CCD area detector system' _diffrn_measurement_method ;Fullsphere data collection in Omega at 0.3 deg, 120 frames, phi=0 deg in phi at 0.3 deg scan with four runs with 600 frames, omega 135,143,156,169 ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ;area detector data,no standard reflections ; _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6224 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 28.18 _reflns_number_total 895 _reflns_number_gt 755 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'Siemens SMART CCD area detector system' _computing_cell_refinement 'Siemens SAINT program Vers.4.050' _computing_data_reduction 'Siemens SAINT program Vers.4.050' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Siemens SHELXL-97 UNIX Version Release 97-1' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version Release 97-1' _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 w=1/[\s^2^(Fo^2^)+(0.0947P)^2^+0.2950P] 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 895 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N4 N 0.61928(8) 0.0372(2) 0.00753(12) 0.0503(5) Uani 1 d . . . H4 H 0.6960 0.0613 0.0123 0.058(10) Uiso 0.50 d PR . . C1 C 0.61340(13) -0.4503(3) 0.17009(14) 0.0508(5) Uani 1 d . . . H1 H 0.6648 -0.5430 0.2100 0.061 Uiso 1 d R . . C2 C 0.65496(11) -0.2772(3) 0.11955(12) 0.0444(4) Uani 1 d . . . H2 H 0.7344 -0.2538 0.1253 0.053 Uiso 1 d R . . C3 C 0.57859(10) -0.1350(2) 0.05889(12) 0.0384(4) Uani 1 d . . . C5 C 0.54300(10) 0.1726(2) -0.05124(12) 0.0389(4) Uani 1 d . . . C6 C 0.58285(11) 0.3512(3) -0.10387(13) 0.0454(4) Uani 1 d . . . H6 H 0.6620 0.3765 -0.0995 0.054 Uiso 1 d R . . C7 C 0.50631(13) 0.4883(3) -0.16219(14) 0.0515(5) Uani 1 d . . . H7 H 0.5338 0.6066 -0.1962 0.062 Uiso 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 N4 0.0217(5) 0.0586(9) 0.0709(10) 0.0129(7) 0.0066(5) -0.0011(4) C1 0.0464(8) 0.0532(11) 0.0519(10) 0.0026(8) 0.0035(6) 0.0080(6) C2 0.0295(6) 0.0544(10) 0.0486(9) -0.0025(7) 0.0028(5) 0.0042(5) C3 0.0250(6) 0.0452(9) 0.0453(9) -0.0040(6) 0.0053(5) -0.0006(5) C5 0.0260(6) 0.0455(9) 0.0458(9) -0.0040(6) 0.0069(5) -0.0021(5) C6 0.0339(7) 0.0505(10) 0.0527(10) -0.0014(7) 0.0096(6) -0.0068(5) C7 0.0524(9) 0.0485(10) 0.0550(11) 0.0019(7) 0.0119(7) -0.0056(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 N4 C5 1.3685(18) . ? N4 C3 1.3692(19) . ? N4 H4 0.9000 . ? C1 C2 1.372(2) . ? C1 C7 1.405(2) 5_655 ? C1 H1 0.9300 . ? C2 C3 1.4063(19) . ? C2 H2 0.9300 . ? C3 C5 1.4260(17) 5_655 ? C5 C6 1.405(2) . ? C5 C3 1.4260(17) 5_655 ? C6 C7 1.374(2) . ? C6 H6 0.9301 . ? C7 C1 1.405(2) 5_655 ? C7 H7 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 N4 C3 119.82(10) . . ? C5 N4 H4 120.1 . . ? C3 N4 H4 120.1 . . ? C2 C1 C7 120.52(14) . 5_655 ? C2 C1 H1 119.8 . . ? C7 C1 H1 119.7 5_655 . ? C1 C2 C3 120.63(12) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.6 . . ? N4 C3 C2 121.06(11) . . ? N4 C3 C5 119.99(13) . 5_655 ? C2 C3 C5 118.96(13) . 5_655 ? N4 C5 C6 120.75(11) . . ? N4 C5 C3 120.19(13) . 5_655 ? C6 C5 C3 119.05(13) . 5_655 ? C7 C6 C5 120.80(12) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C1 120.04(15) . 5_655 ? C6 C7 H7 119.9 . . ? C1 C7 H7 120.0 5_655 . ? _diffrn_measured_fraction_theta_max 0.368 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.368 _refine_diff_density_max 0.320 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.051 # CIF for Complex 4 data_complex-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 3:1 molecular complex of phenazine and 5,10-dihydrophenazine ; _chemical_formula_moiety '3(C12H8N2).(C12H10N2)' _chemical_formula_sum 'C48 H34 N8' _chemical_formula_weight 722.83 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' '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0262(15) _cell_length_b 9.6761(15) _cell_length_c 11.2416(18) _cell_angle_alpha 72.522(2) _cell_angle_beta 80.196(3) _cell_angle_gamma 77.597(3) _cell_volume 908.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1082 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 25.70 _exptl_crystal_description rod _exptl_crystal_colour violet _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_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 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Fullsphere data collection in omega at 0.3 deg scan width, 120 frames, phi=0 deg in phi at 0.3 deg scan width four runs with 600 frames, omega = 135,143,156,169 (deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ; area detector data, no standard reflections ; _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3221 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 22.48 _reflns_number_total 2294 _reflns_number_gt 1296 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'Siemens SMART CCD area detector system' _computing_cell_refinement 'Siemens SAINT program Vers.4.050' _computing_data_reduction 'Siemens SAINT program Vers.4.050' _computing_structure_solution 'Siemens SHELXTL Vers.5.03, SGI-Version' _computing_structure_refinement 'Siemens SHELXL-97 UNIX VERSION Release 97-1' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX VERSION Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX VERSION Release 97-1' _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 w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+0.0916P] 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 2294 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.2075 _refine_ls_wR_factor_gt 0.1579 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.005 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2518(5) 0.2671(5) 0.3093(4) 0.0787(12) Uani 1 d . . . H1 H 0.1559 0.2532 0.2928 0.094 Uiso 1 d R . . C2 C 0.2748(4) 0.4032(5) 0.2995(3) 0.0686(11) Uani 1 d . . . H2 H 0.1953 0.4861 0.2748 0.082 Uiso 1 d R . . C3 C 0.4150(4) 0.4261(4) 0.3250(3) 0.0540(9) Uani 1 d . . . N4 N 0.4345(3) 0.5624(3) 0.3148(2) 0.0588(8) Uani 1 d . . . C5 C 0.5705(4) 0.5776(4) 0.3373(3) 0.0540(9) Uani 1 d . . . C6 C 0.6009(5) 0.7181(4) 0.3271(3) 0.0701(11) Uani 1 d . . . H6 H 0.5226 0.8032 0.3063 0.084 Uiso 1 d R . . C7 C 0.7392(6) 0.7347(5) 0.3462(4) 0.0784(13) Uani 1 d . . . H7 H 0.7575 0.8313 0.3390 0.094 Uiso 1 d R . . C11 C 0.3682(6) 0.1445(5) 0.3440(4) 0.0818(13) Uani 1 d . . . H11 H 0.3506 0.0477 0.3508 0.098 Uiso 1 d R . . C12 C 0.5042(5) 0.1607(4) 0.3681(3) 0.0681(11) Uani 1 d . . . H12 H 0.5819 0.0757 0.3916 0.082 Uiso 1 d R . . C13 C 0.5330(4) 0.3017(4) 0.3584(3) 0.0540(10) Uani 1 d . . . N14 N 0.6692(3) 0.3157(3) 0.3816(3) 0.0594(8) Uani 1 d . . . C15 C 0.6897(4) 0.4532(4) 0.3697(3) 0.0530(9) Uani 1 d . . . C16 C 0.8329(4) 0.4756(5) 0.3893(3) 0.0698(11) Uani 1 d . . . H16 H 0.9132 0.3928 0.4118 0.084 Uiso 1 d R . . C17 C 0.8560(5) 0.6119(6) 0.3771(4) 0.0807(13) Uani 1 d . . . H17 H 0.9540 0.6262 0.3888 0.097 Uiso 1 d R . . C21 C 0.8026(5) 0.6703(5) 0.0358(4) 0.0741(12) Uani 1 d . . . H21 H 0.8993 0.6838 0.0509 0.089 Uiso 1 d R . . C22 C 0.7807(4) 0.5347(4) 0.0430(3) 0.0646(11) Uani 1 d . . . H22 H 0.8618 0.4521 0.0632 0.078 Uiso 1 d R . . C23 C 0.6394(4) 0.5131(4) 0.0206(3) 0.0508(9) Uani 1 d . . . N24 N 0.6183(3) 0.3773(3) 0.0276(2) 0.0549(8) Uani 1 d . . . C25 C 0.4812(4) 0.3629(4) 0.0066(3) 0.0519(9) Uani 1 d . . . C26 C 0.4518(4) 0.2225(4) 0.0143(3) 0.0673(11) Uani 1 d . . . H26 H 0.5304 0.1375 0.0342 0.081 Uiso 1 d R . . C27 C 0.3155(5) 0.2065(5) -0.0069(4) 0.0785(12) Uani 1 d . . . H27 H 0.2976 0.1104 -0.0017 0.094 Uiso 1 d R . . C31 C 0.9857(5) 0.0163(4) 0.3240(4) 0.0725(12) Uani 1 d . . . H31 H 0.9546 0.0475 0.3991 0.087 Uiso 1 d R . . C32 C 0.9122(4) 0.0886(4) 0.2187(4) 0.0626(10) Uani 1 d . . . H32 H 0.8303 0.1699 0.2211 0.075 Uiso 1 d R . . C33 C 0.9551(4) 0.0450(4) 0.1102(3) 0.0520(10) Uani 1 d . . . N34 N 0.8825(4) 0.1161(3) 0.0027(3) 0.0766(10) Uani 1 d . . . H34 H 0.7888 0.2105 0.0066 0.092 Uiso 1 d R . . C35 C 0.9255(4) 0.0744(4) -0.1073(3) 0.0533(9) Uani 1 d . . . C36 C 0.8520(4) 0.1445(4) -0.2130(4) 0.0609(11) Uani 1 d . . . H36 H 0.7692 0.2252 -0.2113 0.073 Uiso 1 d R . . C37 C 0.8966(5) 0.0990(4) -0.3219(4) 0.0704(12) Uani 1 d . . . H37 H 0.8454 0.1486 -0.3953 0.084 Uiso 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 C1 0.075(3) 0.097(4) 0.072(3) -0.027(2) -0.003(2) -0.032(3) C2 0.063(3) 0.069(3) 0.073(3) -0.018(2) -0.011(2) -0.008(2) C3 0.051(2) 0.057(3) 0.051(2) -0.0151(18) -0.0028(17) -0.0077(19) N4 0.057(2) 0.054(2) 0.064(2) -0.0174(15) -0.0090(15) -0.0037(15) C5 0.057(2) 0.053(2) 0.050(2) -0.0167(17) -0.0046(18) -0.0042(19) C6 0.084(3) 0.051(3) 0.076(3) -0.022(2) -0.007(2) -0.007(2) C7 0.096(4) 0.077(3) 0.074(3) -0.030(2) 0.000(2) -0.035(3) C11 0.096(4) 0.066(3) 0.091(3) -0.026(2) -0.002(3) -0.029(3) C12 0.080(3) 0.053(3) 0.069(3) -0.0190(19) 0.000(2) -0.009(2) C13 0.060(3) 0.046(2) 0.055(2) -0.0143(17) -0.0052(18) -0.0049(19) N14 0.059(2) 0.056(2) 0.059(2) -0.0158(15) -0.0088(15) -0.0009(16) C15 0.058(2) 0.052(2) 0.048(2) -0.0140(17) -0.0054(17) -0.009(2) C16 0.062(3) 0.078(3) 0.069(3) -0.017(2) -0.013(2) -0.011(2) C17 0.074(3) 0.101(4) 0.075(3) -0.028(3) -0.005(2) -0.031(3) C21 0.063(3) 0.087(3) 0.081(3) -0.032(2) -0.003(2) -0.022(3) C22 0.058(3) 0.067(3) 0.067(3) -0.021(2) -0.0102(19) -0.001(2) C23 0.049(2) 0.051(2) 0.049(2) -0.0124(17) -0.0051(16) -0.0031(19) N24 0.051(2) 0.0468(19) 0.062(2) -0.0151(14) -0.0070(14) 0.0034(14) C25 0.054(2) 0.046(2) 0.051(2) -0.0110(16) -0.0035(17) -0.0026(19) C26 0.067(3) 0.048(3) 0.083(3) -0.020(2) -0.005(2) -0.003(2) C27 0.078(3) 0.061(3) 0.101(3) -0.032(2) 0.000(2) -0.017(2) C31 0.088(3) 0.071(3) 0.065(3) -0.024(2) -0.014(2) -0.015(2) C32 0.068(3) 0.055(2) 0.068(3) -0.022(2) -0.008(2) -0.0092(19) C33 0.049(2) 0.043(2) 0.061(3) -0.0134(18) -0.0097(18) 0.0008(18) N34 0.079(2) 0.078(2) 0.066(2) -0.0314(19) -0.0298(18) 0.0357(18) C35 0.053(2) 0.046(2) 0.061(2) -0.0140(18) -0.0151(18) -0.0014(18) C36 0.054(2) 0.048(2) 0.078(3) -0.011(2) -0.019(2) -0.0033(18) C37 0.082(3) 0.069(3) 0.062(3) -0.007(2) -0.024(2) -0.018(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 C2 1.346(5) . ? C1 C11 1.411(5) . ? C2 C3 1.420(5) . ? C3 N4 1.336(4) . ? C3 C13 1.427(5) . ? N4 C5 1.341(4) . ? C5 C6 1.412(5) . ? C5 C15 1.433(5) . ? C6 C7 1.352(5) . ? C7 C17 1.408(5) . ? C11 C12 1.351(5) . ? C12 C13 1.413(5) . ? C13 N14 1.342(4) . ? N14 C15 1.346(4) . ? C15 C16 1.419(5) . ? C16 C17 1.342(5) . ? C21 C22 1.345(5) . ? C21 C27 1.415(5) 2_665 ? C22 C23 1.410(5) . ? C23 N24 1.345(4) . ? C23 C25 1.432(5) 2_665 ? N24 C25 1.342(4) . ? C25 C26 1.414(5) . ? C25 C23 1.432(5) 2_665 ? C26 C27 1.341(5) . ? C27 C21 1.415(5) 2_665 ? C31 C37 1.368(5) 2_755 ? C31 C32 1.378(5) . ? C32 C33 1.376(5) . ? C33 N34 1.393(4) . ? C33 C35 1.404(4) 2_755 ? N34 C35 1.383(4) . ? C35 C36 1.379(4) . ? C35 C33 1.405(4) 2_755 ? C36 C37 1.391(5) . ? C37 C31 1.368(5) 2_755 ? 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 C11 120.2(4) . . ? C1 C2 C3 121.0(4) . . ? N4 C3 C2 119.7(4) . . ? N4 C3 C13 121.8(3) . . ? C2 C3 C13 118.5(3) . . ? C3 N4 C5 117.0(3) . . ? N4 C5 C6 120.5(4) . . ? N4 C5 C15 121.3(3) . . ? C6 C5 C15 118.1(4) . . ? C7 C6 C5 120.8(4) . . ? C6 C7 C17 120.7(4) . . ? C12 C11 C1 121.1(4) . . ? C11 C12 C13 120.4(4) . . ? N14 C13 C12 119.6(3) . . ? N14 C13 C3 121.6(3) . . ? C12 C13 C3 118.8(3) . . ? C13 N14 C15 116.6(3) . . ? N14 C15 C16 119.3(3) . . ? N14 C15 C5 121.6(3) . . ? C16 C15 C5 119.2(3) . . ? C17 C16 C15 120.2(4) . . ? C16 C17 C7 121.1(4) . . ? C22 C21 C27 120.9(4) . 2_665 ? C21 C22 C23 120.4(4) . . ? N24 C23 C22 120.1(3) . . ? N24 C23 C25 121.0(3) . 2_665 ? C22 C23 C25 118.9(3) . 2_665 ? C25 N24 C23 117.6(3) . . ? N24 C25 C26 120.1(3) . . ? N24 C25 C23 121.4(3) . 2_665 ? C26 C25 C23 118.5(3) . 2_665 ? C27 C26 C25 120.7(4) . . ? C26 C27 C21 120.6(4) . 2_665 ? C37 C31 C32 120.6(4) 2_755 . ? C33 C32 C31 120.5(4) . . ? C32 C33 N34 121.6(3) . . ? C32 C33 C35 119.5(3) . 2_755 ? N34 C33 C35 118.9(3) . 2_755 ? C35 N34 C33 122.2(3) . . ? C36 C35 N34 121.8(3) . . ? C36 C35 C33 119.3(3) . 2_755 ? N34 C35 C33 118.9(3) . 2_755 ? C35 C36 C37 120.5(4) . . ? C31 C37 C36 119.6(4) 2_755 . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.292 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.054 ## END