Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global #==================================================================== _audit_creation_method 'from SHELXL97 CIF, local template and enCIFer' #=================================================================== _journal_coden_Cambridge 1350 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Scott McKay' _publ_contact_author_address ; Central Missouri State University Department of Chemistry and Physics Warrensburg, MO 64093 ; _publ_contact_author_email mckay@cmsu1.cmsu.edu _publ_contact_author_fax 660-543-4843 _publ_contact_author_phone 660-543-4949 _publ_contact_letter ; Please consider this CIF submission for publication as a communication in CrystEngComm. The CIF has passed the Chester CHECKCIF routines (please see #_publ_section_exptl_refinement) and gives a satisfactory PRINTCIF file. Scott McKay ; _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; A molecular salt of tricyanomethanide anion and a N,N'-dianisylphenazinium dication: cooperative affects of methoxy...methoxy and C=N...N+ intermolecular contacts ; loop_ _publ_author_name _publ_author_address _publ_author_footnote 'McKay, Scott E.' ; Central Missouri State University Department of Chemistry and Physics Warrensburg, MO 64093 ; ? 'Wheeler, Kraig A.' ; Eastern Illinois University Department of Chemistry 600 Lincoln Avenue Charleston, IL 61920 ; ? 'Blackstock, Silas C.' ; University of Alabama Department of Chemistry Tuscaloosa, Alabama 35487 ; ? _publ_section_exptl_refinement ; All H atoms were treated as riding with C---H distances of 0.95 (C~Ar~---H), 0.98 (CH~3~), and U~iso~(H) = 1.2 U~eq~(C) [1.5 U~eq~ for methyl hydrogen atoms]. Riding methyl hydrogen atoms were allowed to rotate freely during refinement. ; #===================================================================== data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 290608' # 5. Chemical Data _chemical_name_systematic ; 2,7-Dimethoxy-5,10-bis(p-anisyl)-5,10-dihydrophenazine tricyanomethanide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H26 N2 O4, C4 N3 ' _chemical_formula_sum 'C32 H26 N5 O4' _chemical_formula_weight 544.58 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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.4791(9) _cell_length_b 21.8079(12) _cell_length_c 7.8598(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.85(3) _cell_angle_gamma 90.00 _cell_volume 2730.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'transparent block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 453 _diffrn_standards_interval_count ? _diffrn_standards_interval_time variable _diffrn_standards_decay_% none _diffrn_reflns_number 7248 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2497 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v5.625 (Bruker, 2001a)' _computing_cell_refinement 'Bruker SMART v5.625 (Bruker, 2001a)' _computing_data_reduction ; Bruker SAINT v6.36A (Bruker, 2002), Bruker XPREP v6.12 (Bruker, 2001b) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000)' _computing_publication_material 'X-SEED, Barbour, 2001' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _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^)+(0.0871P)^2^+1.4252P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2497 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1652 _refine_ls_wR_factor_gt 0.1461 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40583(11) 0.44784(7) 1.1568(2) 0.0414(5) Uani 1 1 d . . . O2 O 0.10497(11) 0.44138(8) 0.2786(2) 0.0416(5) Uani 1 1 d . . . N1 N 0.22241(12) 0.28707(8) 0.8532(2) 0.0268(5) Uani 1 1 d . . . N2 N 0.08789(16) 0.29346(11) 0.0779(3) 0.0510(7) Uani 1 1 d . . . N3 N 0.0000 0.11722(14) 0.2500 0.0601(11) Uani 1 2 d S . . C1 C 0.37274(15) 0.39037(10) 1.1416(3) 0.0313(6) Uani 1 1 d . . . C2 C 0.31359(14) 0.36920(10) 0.9966(3) 0.0298(5) Uani 1 1 d . . . H2 H 0.2942 0.3949 0.8968 0.036 Uiso 1 1 calc R . . C3 C 0.28189(14) 0.30914(10) 0.9973(3) 0.0274(5) Uani 1 1 d . . . C4 C 0.18949(15) 0.22819(9) 0.8535(3) 0.0263(5) Uani 1 1 d . . . C5 C 0.12841(15) 0.20586(10) 0.7093(3) 0.0303(6) Uani 1 1 d . . . H5 H 0.1079 0.2313 0.6094 0.036 Uiso 1 1 calc R . . C6 C 0.09757(15) 0.14716(11) 0.7109(3) 0.0324(6) Uani 1 1 d . . . H6 H 0.0562 0.1322 0.6121 0.039 Uiso 1 1 calc R . . C7 C 0.19235(15) 0.32607(10) 0.7012(3) 0.0276(5) Uani 1 1 d . . . C8 C 0.23968(16) 0.33282(11) 0.5822(3) 0.0332(6) Uani 1 1 d . . . H8 H 0.2912 0.3112 0.5985 0.040 Uiso 1 1 calc R . . C9 C 0.21234(16) 0.37125(11) 0.4375(3) 0.0335(6) Uani 1 1 d . . . H9 H 0.2451 0.3762 0.3551 0.040 Uiso 1 1 calc R . . C10 C 0.13678(15) 0.40224(10) 0.4147(3) 0.0314(6) Uani 1 1 d . . . C11 C 0.08904(16) 0.39469(11) 0.5343(3) 0.0366(6) Uani 1 1 d . . . H11 H 0.0371 0.4157 0.5175 0.044 Uiso 1 1 calc R . . C12 C 0.11670(15) 0.35667(11) 0.6785(3) 0.0338(6) Uani 1 1 d . . . H12 H 0.0841 0.3516 0.7612 0.041 Uiso 1 1 calc R . . C13 C 0.3849(2) 0.48670(12) 1.0056(4) 0.0515(8) Uani 1 1 d . . . H13A H 0.4007 0.4665 0.9074 0.077 Uiso 1 1 calc R . . H13B H 0.4153 0.5256 1.0324 0.077 Uiso 1 1 calc R . . H13C H 0.3244 0.4946 0.9733 0.077 Uiso 1 1 calc R . . C14 C 0.14888(19) 0.44620(12) 0.1443(3) 0.0450(7) Uani 1 1 d . . . H14A H 0.2039 0.4651 0.1934 0.067 Uiso 1 1 calc R . . H14B H 0.1164 0.4716 0.0479 0.067 Uiso 1 1 calc R . . H14C H 0.1565 0.4052 0.0996 0.067 Uiso 1 1 calc R . . C15 C 0.04844(17) 0.26742(11) 0.1551(3) 0.0354(6) Uani 1 1 d . . . C16 C 0.0000 0.23530(15) 0.2500 0.0332(8) Uani 1 2 d S . . C17 C 0.0000 0.17062(17) 0.2500 0.0403(9) Uani 1 2 d S . . 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 O1 0.0499(11) 0.0282(9) 0.0408(10) 0.0000(7) 0.0018(8) -0.0111(8) O2 0.0480(11) 0.0339(9) 0.0418(10) 0.0136(8) 0.0095(8) 0.0078(8) N1 0.0289(10) 0.0260(10) 0.0244(10) 0.0003(7) 0.0047(8) -0.0009(8) N2 0.0574(16) 0.0407(13) 0.0649(16) -0.0052(12) 0.0340(14) -0.0030(11) N3 0.096(3) 0.0286(18) 0.049(2) 0.000 0.0070(19) 0.000 C1 0.0323(13) 0.0271(12) 0.0352(13) -0.0021(10) 0.0101(10) -0.0037(10) C2 0.0322(13) 0.0263(12) 0.0301(12) 0.0001(9) 0.0067(10) 0.0014(10) C3 0.0268(12) 0.0280(12) 0.0280(12) -0.0017(9) 0.0079(10) 0.0009(9) C4 0.0277(12) 0.0241(11) 0.0280(12) -0.0021(9) 0.0089(9) 0.0003(9) C5 0.0316(13) 0.0313(12) 0.0266(11) 0.0004(9) 0.0051(10) 0.0010(10) C6 0.0306(13) 0.0325(13) 0.0314(12) -0.0048(10) 0.0032(10) -0.0035(10) C7 0.0318(13) 0.0242(11) 0.0253(11) -0.0014(9) 0.0047(10) -0.0019(9) C8 0.0336(14) 0.0340(13) 0.0319(13) -0.0002(10) 0.0080(10) 0.0069(10) C9 0.0377(14) 0.0326(12) 0.0320(13) 0.0026(10) 0.0122(11) 0.0008(11) C10 0.0364(14) 0.0242(11) 0.0305(12) 0.0023(9) 0.0029(11) -0.0013(10) C11 0.0311(13) 0.0321(13) 0.0455(14) 0.0074(11) 0.0077(11) 0.0063(10) C12 0.0300(13) 0.0340(13) 0.0395(14) 0.0012(10) 0.0127(11) -0.0010(11) C13 0.069(2) 0.0309(13) 0.0477(16) 0.0058(12) 0.0025(15) -0.0163(13) C14 0.0553(18) 0.0389(14) 0.0411(15) 0.0101(11) 0.0130(13) -0.0018(13) C15 0.0389(14) 0.0294(12) 0.0381(14) -0.0049(11) 0.0100(12) 0.0044(11) C16 0.040(2) 0.0255(16) 0.0339(18) 0.000 0.0089(16) 0.000 C17 0.049(2) 0.038(2) 0.0297(18) 0.000 0.0025(16) 0.000 _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 O1 C1 1.360(3) . ? O1 C13 1.428(3) . ? O2 C10 1.364(3) . ? O2 C14 1.428(3) . ? N1 C3 1.381(3) . y N1 C4 1.394(3) . y N1 C7 1.447(3) . y N2 C15 1.147(3) . y N3 C17 1.165(5) . y C1 C2 1.375(3) . ? C1 C6 1.401(3) 7_557 ? C2 C3 1.411(3) . ? C2 H2 0.9500 . ? C3 C4 1.406(3) 7_557 y C4 C5 1.396(3) . ? C4 C3 1.406(3) 7_557 ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 C1 1.401(3) 7_557 ? C6 H6 0.9500 . ? C7 C8 1.371(3) . ? C7 C12 1.385(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.381(4) . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.410(3) . y C16 C15 1.410(3) 2 ? C16 C17 1.411(5) . y 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 C1 O1 C13 117.89(18) . . ? C10 O2 C14 117.4(2) . . ? C3 N1 C4 120.97(18) . . y C3 N1 C7 119.56(18) . . y C4 N1 C7 119.45(17) . . y O1 C1 C2 124.4(2) . . ? O1 C1 C6 114.7(2) . 7_557 ? C2 C1 C6 120.8(2) . 7_557 ? C1 C2 C3 119.5(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? N1 C3 C4 119.9(2) . 7_557 y N1 C3 C2 120.4(2) . . ? C4 C3 C2 119.7(2) 7_557 . ? N1 C4 C5 121.3(2) . . ? N1 C4 C3 119.15(19) . 7_557 ? C5 C4 C3 119.5(2) . 7_557 ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.9(2) . 7_557 ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 7_557 . ? C8 C7 C12 120.8(2) . . ? C8 C7 N1 119.5(2) . . ? C12 C7 N1 119.7(2) . . ? C7 C8 C9 120.0(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 119.4(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O2 C10 C11 115.9(2) . . ? O2 C10 C9 123.9(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 119.4(2) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 179.9(3) . . ? C15 C16 C15 120.4(3) 2 . y C15 C16 C17 119.78(15) 2 . y C15 C16 C17 119.78(15) . . y N3 C17 C16 180.0 . . ? 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 C13 O1 C1 C2 -7.2(4) . . . . Y C13 O1 C1 C6 173.9(2) . . . 7_557 ? O1 C1 C2 C3 -178.2(2) . . . . ? C6 C1 C2 C3 0.6(4) 7_557 . . . ? C4 N1 C3 C4 0.5(4) . . . 7_557 ? C7 N1 C3 C4 179.1(2) . . . 7_557 ? C4 N1 C3 C2 -178.8(2) . . . . ? C7 N1 C3 C2 -0.3(3) . . . . ? C1 C2 C3 N1 179.9(2) . . . . ? C1 C2 C3 C4 0.6(4) . . . 7_557 ? C3 N1 C4 C5 179.0(2) . . . . ? C7 N1 C4 C5 0.5(3) . . . . ? C3 N1 C4 C3 -0.5(4) . . . 7_557 ? C7 N1 C4 C3 -179.1(2) . . . 7_557 ? N1 C4 C5 C6 179.0(2) . . . . ? C3 C4 C5 C6 -1.5(4) 7_557 . . . ? C4 C5 C6 C1 0.3(4) . . . 7_557 ? C3 N1 C7 C8 80.2(3) . . . . Y C4 N1 C7 C8 -101.2(3) . . . . ? C3 N1 C7 C12 -99.1(3) . . . . ? C4 N1 C7 C12 79.5(3) . . . . ? C12 C7 C8 C9 0.7(3) . . . . ? N1 C7 C8 C9 -178.6(2) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C14 O2 C10 C11 -174.7(2) . . . . ? C14 O2 C10 C9 5.7(3) . . . . Y C8 C9 C10 O2 179.3(2) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? O2 C10 C11 C12 -179.0(2) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C7 -0.4(4) . . . . ? C8 C7 C12 C11 -0.3(3) . . . . ? N1 C7 C12 C11 178.9(2) . . . . ? N2 C15 C16 C15 -178(100) . . . 2 ? N2 C15 C16 C17 2(100) . . . . ? C15 C16 C17 N3 -144(100) 2 . . . ? C15 C16 C17 N3 36(100) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.216 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.075