# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_DHP _database_code_CSD 185376 _journal_coden_Cambridge 188 loop_ _publ_author_name 'Lambert, Christoph' 'Holzapfel, Marco' 'Selinka, Carola' 'Stalke, Dietmar' _publ_contact_author_name 'Prof Christoph Lambert' _publ_contact_author_address ; Institut fur Organische Chemie Universitat Wurzburg Am Hubland Würzburg D-97074 GERMANY ; _publ_contact_author_email 'lambert@chemie.uni-wuerzburg.de' _journal_name_full 'J. Chem. Soc. Perkin 2' _publ_section_title ; Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres ; _ccdc_compound_id 'DHP' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common N,N-dihydrodimethylphenazine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N2' _chemical_formula_weight 210.27 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 hexagonal _symmetry_space_group_name_H-M P63/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 13.178(6) _cell_length_b 13.178(6) _cell_length_c 11.091(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1668.1(13) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type 'empiric' _exptl_absorpt_correction_T_min 0.579650 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS2.0 (Sheldrick 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'BRUKER SMART APEX with D8-Goniometer' _diffrn_measurement_method 'omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4471 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1067 _reflns_number_gt 1062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V5/6.0' _computing_data_reduction 'SAINT-NT V5/6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL-97' _computing_publication_material 'XP in SHELXTL-97' _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^)+(0.0585P)^2^+0.1316P] 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 1062 _refine_ls_number_parameters 81 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.65958(10) 0.83194(9) 0.14231(10) 0.0206(3) Uani 1 1 d . . . C2 C 0.56904(9) 0.85999(9) 0.14253(10) 0.0205(3) Uani 1 1 d . . . C3 C 0.50200(10) 0.84067(10) 0.03975(11) 0.0241(3) Uani 1 1 d . . . H3 H 0.4400 0.8578 0.0400 0.029 Uiso 1 1 calc R . . C4 C 0.52528(11) 0.79614(10) -0.06408(11) 0.0273(3) Uani 1 1 d . . . H4 H 0.4802 0.7847 -0.1348 0.033 Uiso 1 1 calc R . . C5 C 0.61328(11) 0.76869(10) -0.06465(11) 0.0273(3) Uani 1 1 d . . . H5 H 0.6288 0.7386 -0.1358 0.033 Uiso 1 1 calc R . . C6 C 0.67979(10) 0.78500(9) 0.03922(11) 0.0248(3) Uani 1 1 d . . . H6 H 0.7390 0.7639 0.0392 0.030 Uiso 1 1 calc R . . N1 N 0.72498(12) 0.85476(12) 0.2500 0.0228(4) Uani 1 2 d S . . C7 C 0.82527(15) 0.83646(16) 0.2500 0.0304(4) Uani 1 2 d S . . H7A H 0.7977 0.7523 0.2540 0.046 Uiso 1 2 calc SR . . H7B H 0.8749 0.8757 0.3201 0.046 Uiso 0.50 1 calc PR . . H7C H 0.8707 0.8690 0.1759 0.046 Uiso 0.50 1 calc PR . . N2 N 0.55449(11) 0.90912(11) 0.2500 0.0206(3) Uani 1 2 d S . . C8 C 0.46907(16) 0.94838(16) 0.2500 0.0290(4) Uani 1 2 d S . . H8A H 0.3899 0.8803 0.2462 0.044 Uiso 1 2 calc SR . . H8B H 0.4823 0.9987 0.1798 0.044 Uiso 0.50 1 calc PR . . H8C H 0.4775 0.9926 0.3240 0.044 Uiso 0.50 1 calc PR . . 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 0.0213(6) 0.0165(6) 0.0216(7) 0.0037(4) 0.0018(5) 0.0077(5) C2 0.0219(6) 0.0165(6) 0.0207(6) 0.0024(4) 0.0022(5) 0.0079(5) C3 0.0236(6) 0.0217(6) 0.0254(7) 0.0026(5) -0.0009(5) 0.0101(5) C4 0.0342(7) 0.0229(6) 0.0197(7) 0.0011(5) -0.0034(5) 0.0104(5) C5 0.0393(7) 0.0209(6) 0.0196(7) 0.0013(4) 0.0050(5) 0.0134(5) C6 0.0294(7) 0.0210(6) 0.0265(7) 0.0036(5) 0.0058(5) 0.0145(5) N1 0.0221(7) 0.0264(8) 0.0227(8) 0.000 0.000 0.0142(6) C7 0.0257(9) 0.0356(10) 0.0343(11) 0.000 0.000 0.0188(8) N2 0.0218(7) 0.0235(7) 0.0196(8) 0.000 0.000 0.0137(6) C8 0.0313(10) 0.0344(10) 0.0295(10) 0.000 0.000 0.0226(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 C6 1.3877(17) . ? C1 N1 1.4145(14) . ? C1 C2 1.4147(17) . ? C2 C3 1.3856(17) . ? C2 N2 1.4144(14) . ? C3 C4 1.3946(17) . ? C4 C5 1.3766(19) . ? C5 C6 1.3976(18) . ? N1 C1 1.4145(14) 10_556 ? N1 C7 1.457(2) . ? N2 C2 1.4144(14) 10_556 ? N2 C8 1.455(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 N1 123.93(11) . . ? C6 C1 C2 119.53(10) . . ? N1 C1 C2 116.54(10) . . ? C3 C2 N2 123.89(11) . . ? C3 C2 C1 119.61(10) . . ? N2 C2 C1 116.49(10) . . ? C2 C3 C4 120.16(11) . . ? C5 C4 C3 120.39(11) . . ? C4 C5 C6 120.12(11) . . ? C1 C6 C5 120.15(11) . . ? C1 N1 C1 115.22(13) . 10_556 ? C1 N1 C7 118.13(7) . . ? C1 N1 C7 118.13(7) 10_556 . ? C2 N2 C2 114.86(12) 10_556 . ? C2 N2 C8 117.95(7) 10_556 . ? C2 N2 C8 117.95(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.201 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.038