# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/207 # Title of paper (ref. 9/08214J): # Crystal Engineering Using Co-crystallisation of Phenazine with # Dicarboxylic Acids. data_2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzopyrazine trans-2-butenedioc acid ; _chemical_name_common 'Phenazine fumaric acid' _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2, C4 H4 O4' _chemical_formula_sum 'C16 H12 N2 O4' _chemical_formula_weight 296.28 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 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.3361(6) _cell_length_b 8.7650(8) _cell_length_c 14.9520(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.871(8) _cell_angle_gamma 90.00 _cell_volume 690.95(11) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description block _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1261 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 24.94 _reflns_number_total 1212 _reflns_number_gt 1005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 ' _computing_cell_refinement 'CAD4, SETANG ' _computing_data_reduction 'TEXSAN ' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'TEXSAN ' _computing_publication_material 'SHELXS-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^)+(0.0595P)^2^+0.1602P] 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 1212 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.003 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1522(2) 0.23405(13) 0.04879(7) 0.0384(3) Uani 1 1 d . . . H1O H 0.004(4) 0.281(3) 0.0269(14) 0.067(6) Uiso 1 1 d . . . O2 O 0.0901(2) 0.10892(14) -0.08276(8) 0.0451(3) Uani 1 1 d . . . N1 N 0.7107(2) 0.40156(14) 0.00738(8) 0.0304(3) Uani 1 1 d . . . C1 C 0.7820(3) 0.5598(2) 0.23392(11) 0.0431(4) Uani 1 1 d . . . H1 H 0.8909 0.5527 0.2887 0.050(3) Uiso 1 1 calc R . . C2 C 0.8258(3) 0.4737(2) 0.16281(11) 0.0384(4) Uani 1 1 d . . . H2 H 0.9635 0.4074 0.1693 0.050(3) Uiso 1 1 calc R . . C3 C 0.6631(3) 0.48389(17) 0.07842(10) 0.0295(4) Uani 1 1 d . . . C4 C 0.5519(3) 0.41540(17) -0.07108(10) 0.0289(4) Uani 1 1 d . . . C5 C 0.5915(3) 0.32807(19) -0.14738(10) 0.0366(4) Uani 1 1 d . . . H5 H 0.7301 0.2627 -0.1435 0.050(3) Uiso 1 1 calc R . . C6 C 0.4281(3) 0.3394(2) -0.22592(11) 0.0417(4) Uani 1 1 d . . . H6 H 0.4540 0.2802 -0.2753 0.050(3) Uiso 1 1 calc R . . C7 C 0.2129(3) 0.13197(16) -0.00963(10) 0.0301(4) Uani 1 1 d . . . C8 C 0.4500(3) 0.04943(18) 0.02483(10) 0.0332(4) Uani 1 1 d . . . H8 H 0.5302 0.0684 0.0835 0.042(5) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0362(6) 0.0365(6) 0.0406(6) -0.0057(5) 0.0004(5) 0.0139(5) O2 0.0409(6) 0.0482(7) 0.0424(7) -0.0086(5) -0.0058(5) 0.0146(5) N1 0.0284(6) 0.0280(7) 0.0343(7) 0.0020(5) 0.0032(5) 0.0050(5) C1 0.0445(9) 0.0487(10) 0.0331(8) 0.0029(8) -0.0034(7) 0.0059(8) C2 0.0335(8) 0.0390(9) 0.0407(9) 0.0045(7) -0.0007(7) 0.0104(7) C3 0.0277(7) 0.0264(8) 0.0343(8) 0.0039(6) 0.0042(6) 0.0020(6) C4 0.0265(7) 0.0269(8) 0.0329(8) 0.0040(6) 0.0035(6) 0.0012(6) C5 0.0364(8) 0.0353(9) 0.0386(9) 0.0004(7) 0.0075(7) 0.0077(7) C6 0.0480(9) 0.0444(10) 0.0326(9) -0.0019(7) 0.0064(7) 0.0069(8) C7 0.0295(7) 0.0253(7) 0.0351(8) -0.0001(6) 0.0041(6) 0.0022(6) C8 0.0320(8) 0.0321(8) 0.0343(8) -0.0016(6) 0.0013(6) 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 O1 C7 1.3251(18) . ? O2 C7 1.2022(18) . ? N1 C3 1.3405(19) . ? N1 C4 1.3427(19) . ? C1 C2 1.353(2) . ? C1 C6 1.418(2) 3_665 ? C2 C3 1.420(2) . ? C3 C4 1.438(2) 3_665 ? C4 C5 1.416(2) . ? C4 C3 1.438(2) 3_665 ? C5 C6 1.354(2) . ? C6 C1 1.418(2) 3_665 ? C7 C8 1.479(2) . ? C8 C8 1.307(3) 3_655 ? 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 C3 N1 C4 118.19(12) . . ? C2 C1 C6 120.76(15) . 3_665 ? C1 C2 C3 120.46(14) . . ? N1 C3 C2 120.37(13) . . ? N1 C3 C4 121.10(13) . 3_665 ? C2 C3 C4 118.53(14) . 3_665 ? N1 C4 C5 120.16(13) . . ? N1 C4 C3 120.71(13) . 3_665 ? C5 C4 C3 119.11(13) . 3_665 ? C6 C5 C4 120.19(14) . . ? C5 C6 C1 120.92(15) . 3_665 ? O2 C7 O1 123.96(13) . . ? O2 C7 C8 123.49(14) . . ? O1 C7 C8 112.55(12) . . ? C8 C8 C7 121.89(18) 3_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.6(3) 3_665 . . . ? C4 N1 C3 C2 -179.78(13) . . . . ? C4 N1 C3 C4 -0.1(2) . . . 3_665 ? C1 C2 C3 N1 178.22(15) . . . . ? C1 C2 C3 C4 -1.5(2) . . . 3_665 ? C3 N1 C4 C5 -178.58(13) . . . . ? C3 N1 C4 C3 0.1(2) . . . 3_665 ? N1 C4 C5 C6 178.50(15) . . . . ? C3 C4 C5 C6 -0.2(2) 3_665 . . . ? C4 C5 C6 C1 1.1(3) . . . 3_665 ? O2 C7 C8 C8 3.9(3) . . . 3_655 ? O1 C7 C8 C8 -175.83(19) . . . 3_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.133 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.044 #===END data_2d _audit_creation_method SHELXL _chemical_name_systematic ; dibenzopyrazine trans-2-methyl-2-butenedioic acid ; _chemical_name_common 'Phenazine mesaconic acid' _chemical_formula_moiety 'C12 H8 N2, C5 H6 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H14 N2 O4' _chemical_formula_weight 310.30 _chemical_melting_point ? _chemical_compound_source Aldrich 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 'C 1 2/c 1' 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 26.833(26) _cell_length_b 7.095(4) _cell_length_c 19.613(27) _cell_angle_alpha 90.00 _cell_angle_beta 127.46(7) _cell_angle_gamma 90.00 _cell_volume 2963.9(53) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description 'rectangular plate ' _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured ' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2689 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2601 _reflns_number_observed 1733 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 ' _computing_cell_refinement 'CAD4, SETANG ' _computing_data_reduction 'TEXSAN ' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'TEXSAN ' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0606P)^2^+1.0880P] 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 0.0059(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2601 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_obs 0.0407 _refine_ls_wR_factor_all 0.1183 _refine_ls_wR_factor_obs 0.1010 _refine_ls_goodness_of_fit_all 1.014 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.014 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max 0.011 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O3 O 0.46646(7) 0.7227(2) 0.04498(9) 0.0493(4) Uani 1 d . . H3O H 0.4274(13) 0.6864(42) 0.0230(17) 0.084(9) Uiso 1 d . . O1 O 0.63187(8) 0.8758(3) -0.04958(11) 0.0593(5) Uani 1 d . . H1O H 0.6737(15) 0.9134(44) -0.0206(18) 0.100(10) Uiso 1 d . . O2 O 0.65233(7) 0.9206(3) 0.07641(10) 0.0786(7) Uani 1 d . . O4 O 0.42986(7) 0.6705(3) -0.08961(11) 0.0724(6) Uani 1 d . . N1 N 0.64893(7) 0.3835(3) -0.00896(10) 0.0383(4) Uani 1 d . . N2 N 0.75412(8) 0.5105(2) 0.00410(11) 0.0359(4) Uani 1 d . . C16 C 0.47176(9) 0.7201(3) -0.01811(13) 0.0397(5) Uani 1 d . . C15 C 0.53428(9) 0.7829(3) 0.01041(13) 0.0403(5) Uani 1 d . . H15 H 0.56479(9) 0.8035(3) 0.06888(13) 0.044(6) Uiso 1 calc R . C14 C 0.55039(9) 0.8122(3) -0.04060(12) 0.0379(5) Uani 1 d . . C17 C 0.50881(11) 0.7927(5) -0.13614(14) 0.0677(8) Uani 1 d . . H17A H 0.5256(7) 0.6983(27) -0.1521(2) 0.153(9) Uiso 1 calc R . H17B H 0.5067(10) 0.9111(11) -0.1615(2) 0.153(9) Uiso 1 calc R . H17C H 0.4675(4) 0.7563(38) -0.1562(2) 0.153(9) Uiso 1 calc R . C13 C 0.61712(9) 0.8750(3) 0.00318(13) 0.0408(5) Uani 1 d . . C11 C 0.70704(10) 0.4222(4) 0.14256(13) 0.0487(6) Uani 1 d . . H11 H 0.67325(10) 0.3772(4) 0.13969(13) 0.060(2) Uiso 1 calc R . C10 C 0.76027(11) 0.4752(4) 0.21901(14) 0.0556(7) Uani 1 d . . H10 H 0.76276(11) 0.4655(4) 0.26829(14) 0.060(2) Uiso 1 calc R . C9 C 0.81216(10) 0.5452(4) 0.22527(14) 0.0505(6) Uani 1 d . . H9 H 0.84808(10) 0.5830(4) 0.27838(14) 0.060(2) Uiso 1 calc R . C8 C 0.81022(9) 0.5577(3) 0.15519(13) 0.0431(5) Uani 1 d . . H8 H 0.84483(9) 0.6033(3) 0.16024(13) 0.060(2) Uiso 1 calc R . C7 C 0.75559(9) 0.5016(3) 0.07368(12) 0.0333(5) Uani 1 d . . C6 C 0.70088(8) 0.4583(3) -0.07194(12) 0.0331(5) Uani 1 d . . C5 C 0.69726(10) 0.4665(3) -0.14681(13) 0.0435(5) Uani 1 d . . H5 H 0.73188(10) 0.5065(3) -0.14302(13) 0.060(2) Uiso 1 calc R . C4 C 0.64420(11) 0.4171(4) -0.22349(14) 0.0526(6) Uani 1 d . . H4 H 0.64223(11) 0.4247(4) -0.27242(14) 0.060(2) Uiso 1 calc R . C3 C 0.59136(10) 0.3535(4) -0.23034(14) 0.0530(7) Uani 1 d . . H3 H 0.55503(10) 0.3192(4) -0.28375(14) 0.060(2) Uiso 1 calc R . C2 C 0.59301(9) 0.3421(4) -0.16027(13) 0.0485(6) Uani 1 d . . H2 H 0.55788(9) 0.2996(4) -0.16593(13) 0.060(2) Uiso 1 calc R . C1 C 0.64751(9) 0.3941(3) -0.07850(12) 0.0352(5) Uani 1 d . . C12 C 0.70236(9) 0.4346(3) 0.06703(12) 0.0352(5) Uani 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 O3 0.0391(8) 0.0728(12) 0.0462(9) 0.0002(8) 0.0312(8) -0.0100(8) O1 0.0446(9) 0.0915(14) 0.0572(10) -0.0154(9) 0.0390(8) -0.0245(9) O2 0.0413(10) 0.149(2) 0.0469(10) -0.0167(11) 0.0275(9) -0.0333(11) O4 0.0423(9) 0.130(2) 0.0541(11) -0.0205(10) 0.0341(9) -0.0301(10) N1 0.0301(9) 0.0526(12) 0.0400(9) 0.0022(8) 0.0253(8) -0.0001(8) N2 0.0329(9) 0.0419(11) 0.0419(9) 0.0007(7) 0.0274(8) -0.0037(7) C16 0.0324(10) 0.0504(14) 0.0411(12) 0.0006(10) 0.0248(10) -0.0032(10) C15 0.0309(10) 0.0502(14) 0.0407(12) 0.0012(10) 0.0222(10) -0.0038(10) C14 0.0318(10) 0.0454(13) 0.0414(11) -0.0010(9) 0.0247(9) -0.0038(9) C17 0.0471(13) 0.117(2) 0.0439(14) -0.0112(14) 0.0305(12) -0.024(2) C13 0.0343(11) 0.0530(14) 0.0415(12) 0.0003(10) 0.0264(10) -0.0049(10) C11 0.0370(12) 0.078(2) 0.0422(12) -0.0002(11) 0.0297(10) -0.0054(12) C10 0.0462(13) 0.089(2) 0.0403(12) -0.0028(12) 0.0308(11) 0.0001(13) C9 0.0380(12) 0.069(2) 0.0428(12) -0.0080(11) 0.0237(10) -0.0047(12) C8 0.0350(11) 0.0501(14) 0.0485(12) -0.0066(10) 0.0276(10) -0.0079(10) C7 0.0320(10) 0.0349(12) 0.0398(11) -0.0014(9) 0.0253(9) -0.0016(9) C6 0.0310(10) 0.0352(12) 0.0398(11) 0.0042(9) 0.0250(9) 0.0025(9) C5 0.0441(12) 0.0548(15) 0.0466(12) 0.0052(11) 0.0353(11) -0.0022(11) C4 0.0550(14) 0.072(2) 0.0397(12) 0.0046(11) 0.0332(11) 0.0015(13) C3 0.0373(12) 0.079(2) 0.0374(12) -0.0033(11) 0.0199(10) -0.0028(12) C2 0.0306(11) 0.072(2) 0.0451(12) -0.0028(11) 0.0239(10) -0.0038(11) C1 0.0305(10) 0.0426(13) 0.0395(11) 0.0025(9) 0.0249(9) 0.0020(9) C12 0.0296(10) 0.0440(12) 0.0384(11) 0.0005(9) 0.0240(9) 0.0003(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C16 1.329(3) . ? O1 C13 1.314(3) . ? O2 C13 1.187(3) . ? O4 C16 1.198(3) . ? N1 C1 1.343(3) . ? N1 C12 1.345(3) . ? N2 C7 1.343(3) . ? N2 C6 1.346(3) . ? C16 C15 1.478(3) . ? C15 C14 1.326(3) . ? C14 C17 1.494(4) . ? C14 C13 1.507(3) . ? C11 C10 1.351(4) . ? C11 C12 1.411(3) . ? C10 C9 1.411(3) . ? C9 C8 1.346(3) . ? C8 C7 1.419(3) . ? C7 C12 1.434(3) . ? C6 C5 1.413(3) . ? C6 C1 1.432(3) . ? C5 C4 1.344(4) . ? C4 C3 1.414(3) . ? C3 C2 1.350(3) . ? C2 C1 1.412(3) . ? 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 N1 C12 117.6(2) . . ? C7 N2 C6 118.0(2) . . ? O4 C16 O3 122.6(2) . . ? O4 C16 C15 124.9(2) . . ? O3 C16 C15 112.5(2) . . ? C14 C15 C16 125.3(2) . . ? C15 C14 C17 126.5(2) . . ? C15 C14 C13 115.9(2) . . ? C17 C14 C13 117.6(2) . . ? O2 C13 O1 123.5(2) . . ? O2 C13 C14 124.4(2) . . ? O1 C13 C14 112.0(2) . . ? C10 C11 C12 120.4(2) . . ? C11 C10 C9 121.1(2) . . ? C8 C9 C10 120.7(2) . . ? C9 C8 C7 120.2(2) . . ? N2 C7 C8 120.2(2) . . ? N2 C7 C12 120.7(2) . . ? C8 C7 C12 119.0(2) . . ? N2 C6 C5 119.8(2) . . ? N2 C6 C1 121.1(2) . . ? C5 C6 C1 119.1(2) . . ? C4 C5 C6 120.6(2) . . ? C5 C4 C3 120.5(2) . . ? C2 C3 C4 120.8(2) . . ? C3 C2 C1 120.7(2) . . ? N1 C1 C2 120.6(2) . . ? N1 C1 C6 121.2(2) . . ? C2 C1 C6 118.2(2) . . ? N1 C12 C11 120.0(2) . . ? N1 C12 C7 121.4(2) . . ? C11 C12 C7 118.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C16 C15 C14 7.6(4) . . . . ? O3 C16 C15 C14 -172.8(2) . . . . ? C16 C15 C14 C17 1.6(4) . . . . ? C16 C15 C14 C13 -179.7(2) . . . . ? C15 C14 C13 O2 -9.5(3) . . . . ? C17 C14 C13 O2 169.3(3) . . . . ? C15 C14 C13 O1 171.2(2) . . . . ? C17 C14 C13 O1 -10.0(3) . . . . ? C12 C11 C10 C9 0.4(4) . . . . ? C11 C10 C9 C8 -1.1(4) . . . . ? C10 C9 C8 C7 0.4(4) . . . . ? C6 N2 C7 C8 -179.1(2) . . . . ? C6 N2 C7 C12 1.3(3) . . . . ? C9 C8 C7 N2 -178.6(2) . . . . ? C9 C8 C7 C12 1.0(3) . . . . ? C7 N2 C6 C5 179.6(2) . . . . ? C7 N2 C6 C1 -0.4(3) . . . . ? N2 C6 C5 C4 -179.2(2) . . . . ? C1 C6 C5 C4 0.8(3) . . . . ? C6 C5 C4 C3 -0.9(4) . . . . ? C5 C4 C3 C2 0.3(4) . . . . ? C4 C3 C2 C1 0.2(4) . . . . ? C12 N1 C1 C2 179.8(2) . . . . ? C12 N1 C1 C6 -0.3(3) . . . . ? C3 C2 C1 N1 179.7(2) . . . . ? C3 C2 C1 C6 -0.3(3) . . . . ? N2 C6 C1 N1 -0.2(3) . . . . ? C5 C6 C1 N1 179.8(2) . . . . ? N2 C6 C1 C2 179.8(2) . . . . ? C5 C6 C1 C2 -0.3(3) . . . . ? C1 N1 C12 C11 -178.5(2) . . . . ? C1 N1 C12 C7 1.2(3) . . . . ? C10 C11 C12 N1 -179.2(2) . . . . ? C10 C11 C12 C7 1.0(3) . . . . ? N2 C7 C12 N1 -1.8(3) . . . . ? C8 C7 C12 N1 178.6(2) . . . . ? N2 C7 C12 C11 177.9(2) . . . . ? C8 C7 C12 C11 -1.7(3) . . . . ? _refine_diff_density_max 0.208 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.039 #===END data_3c _audit_creation_method SHELXL _chemical_name_systematic ; dibenzopyrazine bis(cis-2-butenedioic acid) ; _chemical_name_common 'Phenazine bis(maleic acid)' _chemical_formula_moiety 'C12 H8 N2, 2(C4 H4 O4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H16 N2 O8' _chemical_formula_weight 412.35 _chemical_melting_point ? _chemical_compound_source 'Sigma-Aldrich Company Ltd.' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.513(2) _cell_length_b 6.733(2) _cell_length_c 13.026(7) _cell_angle_alpha 95.32(3) _cell_angle_beta 99.39(4) _cell_angle_gamma 100.24(3) _cell_volume 465.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 15 _exptl_crystal_description yellow _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured ' _exptl_crystal_F_000 214 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1723 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1644 _reflns_number_observed 1368 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 ' _computing_cell_refinement 'CAD4, SETANG ' _computing_data_reduction 'TEXSAN ' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'TEXSAN ' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0524P)^2^+0.1590P] 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 0.1299(120) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1644 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_obs 0.0339 _refine_ls_wR_factor_all 0.0986 _refine_ls_wR_factor_obs 0.0887 _refine_ls_goodness_of_fit_all 1.005 _refine_ls_goodness_of_fit_obs 1.002 _refine_ls_restrained_S_all 1.005 _refine_ls_restrained_S_obs 1.002 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1864(2) 0.3680(2) 0.95486(10) 0.0523(4) Uani 1 d . . H1O H 0.3324(62) 0.4593(53) 0.9341(26) 0.126(12) Uiso 1 d . . O2 O 0.4439(3) 0.3968(2) 1.10778(11) 0.0647(5) Uani 1 d . . O3 O 0.3536(2) 0.0872(2) 1.31305(9) 0.0470(4) Uani 1 d . . H3O H 0.4981(48) 0.0559(38) 1.3432(20) 0.076(7) Uiso 1 d . . O4 O 0.4483(3) -0.0349(3) 1.16363(11) 0.0677(5) Uani 1 d . . N1 N 0.2222(2) -0.0133(2) 0.56730(10) 0.0329(3) Uani 1 d . . C1 C 0.2389(3) 0.3306(2) 1.05085(13) 0.0390(4) Uani 1 d . . C2 C 0.0332(3) 0.2039(2) 1.08774(13) 0.0369(4) Uani 1 d . . H2 H -0.1303(3) 0.2095(2) 1.05798(13) 0.045(5) Uiso 1 calc R . C3 C 0.0662(3) 0.0824(2) 1.16060(12) 0.0347(4) Uani 1 d . . H3 H -0.0761(3) 0.0168(2) 1.18250(12) 0.045(5) Uiso 1 calc R . C4 C 0.3124(3) 0.0416(2) 1.21067(12) 0.0353(4) Uani 1 d . . C5 C 0.0835(3) 0.4503(3) 0.68736(14) 0.0450(4) Uani 1 d . . H5 H 0.1511(3) 0.5515(3) 0.74345(14) 0.048(3) Uiso 1 calc R . C6 C 0.2039(3) 0.2961(3) 0.66991(13) 0.0389(4) Uani 1 d . . H6 H 0.3523(3) 0.2909(3) 0.71429(13) 0.048(3) Uiso 1 calc R . C7 C 0.1045(3) 0.1418(2) 0.58401(12) 0.0311(4) Uani 1 d . . C8 C 0.1229(3) -0.1546(2) 0.48463(12) 0.0308(4) Uani 1 d . . C9 C 0.2442(3) -0.3188(3) 0.46222(13) 0.0385(4) Uani 1 d . . H9 H 0.3926(3) -0.3285(3) 0.50528(13) 0.048(3) Uiso 1 calc R . C10 C 0.1447(3) -0.4605(3) 0.37864(14) 0.0441(4) Uani 1 d . . H10 H 0.2267(3) -0.5663(3) 0.36413(14) 0.048(3) Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0494(8) 0.0621(9) 0.0409(7) 0.0199(6) -0.0032(6) 0.0025(6) O2 0.0493(8) 0.0810(10) 0.0503(8) 0.0287(7) -0.0127(6) -0.0139(7) O3 0.0425(7) 0.0638(8) 0.0370(7) 0.0052(6) -0.0031(5) 0.0264(6) O4 0.0574(9) 0.1128(13) 0.0475(8) 0.0144(8) 0.0124(7) 0.0507(9) N1 0.0295(6) 0.0382(7) 0.0316(7) 0.0076(5) 0.0011(5) 0.0112(5) C1 0.0401(9) 0.0378(9) 0.0376(9) 0.0088(7) -0.0016(7) 0.0092(7) C2 0.0307(8) 0.0423(9) 0.0367(9) 0.0054(7) -0.0011(6) 0.0112(7) C3 0.0292(8) 0.0394(9) 0.0350(9) 0.0050(7) 0.0040(6) 0.0071(6) C4 0.0329(8) 0.0387(9) 0.0366(9) 0.0122(7) 0.0058(7) 0.0096(7) C5 0.0504(10) 0.0443(10) 0.0373(9) -0.0027(7) 0.0006(8) 0.0125(8) C6 0.0364(9) 0.0449(9) 0.0335(8) 0.0033(7) -0.0016(7) 0.0114(7) C7 0.0289(8) 0.0359(8) 0.0305(8) 0.0094(6) 0.0046(6) 0.0099(6) C8 0.0282(7) 0.0355(8) 0.0299(8) 0.0086(6) 0.0033(6) 0.0091(6) C9 0.0339(8) 0.0433(9) 0.0408(9) 0.0080(7) 0.0024(7) 0.0167(7) C10 0.0476(10) 0.0416(9) 0.0465(10) 0.0027(8) 0.0073(8) 0.0205(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 O1 C1 1.295(2) . ? O2 C1 1.230(2) . ? O3 C4 1.313(2) . ? O4 C4 1.196(2) . ? N1 C8 1.340(2) . ? N1 C7 1.343(2) . ? C1 C2 1.468(2) . ? C2 C3 1.320(2) . ? C3 C4 1.490(2) . ? C5 C6 1.349(2) . ? C5 C10 1.420(3) 2_556 ? C6 C7 1.419(2) . ? C7 C8 1.437(2) 2_556 ? C8 C9 1.421(2) . ? C8 C7 1.437(2) 2_556 ? C9 C10 1.351(3) . ? C10 C5 1.420(3) 2_556 ? 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 C8 N1 C7 118.24(13) . . ? O2 C1 O1 123.1(2) . . ? O2 C1 C2 122.0(2) . . ? O1 C1 C2 114.87(15) . . ? C3 C2 C1 123.97(15) . . ? C2 C3 C4 125.45(15) . . ? O4 C4 O3 124.3(2) . . ? O4 C4 C3 123.8(2) . . ? O3 C4 C3 111.79(14) . . ? C6 C5 C10 121.0(2) . 2_556 ? C5 C6 C7 120.2(2) . . ? N1 C7 C6 120.26(14) . . ? N1 C7 C8 120.72(14) . 2_556 ? C6 C7 C8 119.02(14) . 2_556 ? N1 C8 C9 120.27(14) . . ? N1 C8 C7 121.04(14) . 2_556 ? C9 C8 C7 118.68(14) . 2_556 ? C10 C9 C8 120.24(15) . . ? C9 C10 C5 120.9(2) . 2_556 ? 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 O2 C1 C2 C3 -29.3(3) . . . . ? O1 C1 C2 C3 151.3(2) . . . . ? C1 C2 C3 C4 -5.1(3) . . . . ? C2 C3 C4 O4 -61.7(3) . . . . ? C2 C3 C4 O3 122.5(2) . . . . ? C10 C5 C6 C7 0.6(3) 2_556 . . . ? C8 N1 C7 C6 -179.38(14) . . . . ? C8 N1 C7 C8 0.5(2) . . . 2_556 ? C5 C6 C7 N1 -179.1(2) . . . . ? C5 C6 C7 C8 1.0(2) . . . 2_556 ? C7 N1 C8 C9 178.41(14) . . . . ? C7 N1 C8 C7 -0.5(2) . . . 2_556 ? N1 C8 C9 C10 -179.7(2) . . . . ? C7 C8 C9 C10 -0.8(2) 2_556 . . . ? C8 C9 C10 C5 -0.9(3) . . . 2_556 ? _refine_diff_density_max 0.243 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.034 #===END data_3d _audit_creation_method SHELXL _chemical_name_systematic ; dibenzopyrazine bis(cis-2-methyl-2-butenedioic acid) ; _chemical_name_common 'Phenazine bis (citraconic acid)' _chemical_formula_moiety 'C12 H8 N2, 2(C5 H6 O4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H10 N O4' _chemical_formula_weight 220.20 _chemical_melting_point ? _chemical_compound_source 'Sigma-Aldrich Company Ltd.' 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 'P 1 21/n 1' 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 6.6790(9) _cell_length_b 18.660(2) _cell_length_c 8.9330(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.13(2) _cell_angle_gamma 90.00 _cell_volume 1074.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description parallelopiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1844 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.96 _reflns_number_total 938 _reflns_number_observed 495 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 ' _computing_cell_refinement 'CAD4, SETANG ' _computing_data_reduction 'TEXSAN ' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'TEXSAN ' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0742P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 938 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_obs 0.0393 _refine_ls_wR_factor_all 0.1262 _refine_ls_wR_factor_obs 0.0867 _refine_ls_goodness_of_fit_all 0.926 _refine_ls_goodness_of_fit_obs 0.963 _refine_ls_restrained_S_all 0.926 _refine_ls_restrained_S_obs 0.963 _refine_ls_shift/esd_max -0.024 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.4791(9) 0.8279(3) 0.2233(8) 0.076(4) Uani 1 d . . O2 O 0.4549(7) 0.8883(2) 0.4349(5) 0.063(2) Uani 1 d . . H2O H 0.5901(132) 0.9103(35) 0.4278(111) 0.116(26) Uiso 1 d . . O3 O 0.1565(6) 0.9548(2) 0.1417(5) 0.061(2) Uani 1 d . . O4 O -0.1691(6) 0.9282(2) 0.0198(5) 0.063(2) Uani 1 d . . H4O H -0.1672(117) 0.9744(31) -0.0346(82) 0.101(21) Uiso 1 d . . N1 N 0.1779(7) 0.0432(2) 0.5346(6) 0.052(2) Uani 1 d . . C1 C 0.3290(9) -0.0924(3) 0.8283(7) 0.068(4) Uani 1 d . . H1 H 0.4414(9) -0.1040(3) 0.9109(7) 0.065(7) Uiso 1 calc R . C2 C 0.3374(8) -0.0344(3) 0.7447(6) 0.059(3) Uani 1 d . . H2 H 0.4552(8) -0.0057(3) 0.7699(6) 0.065(7) Uiso 1 calc R . C3 C 0.1688(8) -0.0154(3) 0.6167(6) 0.043(3) Uani 1 d . . C4 C 0.0117(9) 0.0602(2) 0.4164(7) 0.051(3) Uani 1 d . . C5 C -0.0135(9) -0.1216(3) 0.6745(7) 0.056(3) Uani 1 d . . H5 H -0.1288(9) -0.1515(3) 0.6522(7) 0.065(7) Uiso 1 calc R . C6 C 0.1505(10) -0.1372(3) 0.7937(8) 0.074(4) Uani 1 d . . H6 H 0.1472(10) -0.1776(3) 0.8540(8) 0.065(7) Uiso 1 calc R . C8 C 0.3854(12) 0.8469(3) 0.3129(9) 0.047(4) Uani 1 d . . C9 C 0.1671(9) 0.8210(2) 0.3092(7) 0.037(3) Uani 1 d . . C10 C 0.0007(9) 0.8524(2) 0.2183(7) 0.047(3) Uani 1 d . . H10 H -0.1281(9) 0.8324(2) 0.2143(7) 0.049(14) Uiso 1 calc R . C11 C 0.0057(8) 0.9156(2) 0.1249(7) 0.041(3) Uani 1 d . . C12 C 0.1601(11) 0.7569(3) 0.4060(9) 0.075(4) Uani 1 d . . H12A H 0.2261(69) 0.7676(8) 0.5126(12) 0.122(15) Uiso 1 calc R . H12B H 0.2313(61) 0.7179(8) 0.3722(37) 0.122(15) Uiso 1 calc R . H12C H 0.0183(11) 0.7437(16) 0.3960(43) 0.122(15) Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.056(5) 0.083(3) 0.096(5) -0.015(3) 0.034(6) -0.008(3) O2 0.047(3) 0.084(2) 0.056(3) -0.011(3) 0.011(3) -0.020(3) O3 0.046(3) 0.055(2) 0.072(3) 0.011(2) -0.006(3) -0.009(2) O4 0.039(3) 0.064(2) 0.073(3) 0.007(2) -0.007(3) -0.002(2) N1 0.041(3) 0.056(2) 0.052(3) -0.014(3) 0.000(4) -0.002(2) C1 0.053(5) 0.076(4) 0.062(5) 0.002(4) -0.008(5) 0.002(3) C2 0.043(4) 0.066(3) 0.059(4) -0.005(3) -0.002(5) -0.004(3) C3 0.037(4) 0.052(3) 0.042(4) -0.005(3) 0.013(5) 0.000(3) C4 0.044(4) 0.051(3) 0.053(5) -0.012(3) 0.003(5) -0.002(3) C5 0.048(5) 0.059(3) 0.064(4) -0.001(4) 0.018(5) -0.006(3) C6 0.064(5) 0.066(3) 0.082(5) 0.012(4) 0.002(6) 0.000(3) C8 0.037(5) 0.046(3) 0.056(6) 0.002(4) 0.011(6) 0.003(3) C9 0.037(4) 0.043(2) 0.040(4) 0.002(3) 0.027(5) -0.008(3) C10 0.036(4) 0.052(3) 0.053(5) -0.010(3) 0.014(5) -0.006(3) C11 0.031(3) 0.048(3) 0.046(4) -0.008(3) 0.012(4) 0.000(3) C12 0.066(5) 0.065(3) 0.095(6) 0.023(4) 0.020(7) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.192(12) . ? O2 C8 1.317(8) . ? O3 C11 1.220(7) . ? O4 C11 1.314(4) . ? N1 C3 1.326(7) . ? N1 C4 1.355(5) . ? C1 C2 1.324(8) . ? C1 C6 1.422(9) . ? C2 C3 1.424(5) . ? C3 C4 1.433(8) 3_556 ? C4 C5 1.406(8) 3_556 ? C4 C3 1.433(8) 3_556 ? C5 C6 1.346(6) . ? C5 C4 1.406(8) 3_556 ? C8 C9 1.528(13) . ? C9 C10 1.329(6) . ? C9 C12 1.483(9) . ? C10 C11 1.451(8) . ? 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 C3 N1 C4 118.6(4) . . ? C2 C1 C6 120.9(4) . . ? C1 C2 C3 121.0(5) . . ? N1 C3 C2 120.6(4) . . ? N1 C3 C4 121.6(4) . 3_556 ? C2 C3 C4 117.8(5) . 3_556 ? N1 C4 C5 120.9(5) . 3_556 ? N1 C4 C3 119.8(5) . 3_556 ? C5 C4 C3 119.3(4) 3_556 3_556 ? C6 C5 C4 120.4(5) . 3_556 ? C5 C6 C1 120.5(6) . . ? O1 C8 O2 126.6(8) . . ? O1 C8 C9 123.8(6) . . ? O2 C8 C9 109.4(9) . . ? C10 C9 C12 124.3(6) . . ? C10 C9 C8 120.9(6) . . ? C12 C9 C8 114.7(5) . . ? C9 C10 C11 124.7(6) . . ? O3 C11 O4 122.1(5) . . ? O3 C11 C10 123.9(3) . . ? O4 C11 C10 114.0(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.5(11) . . . . ? C4 N1 C3 C2 -178.3(6) . . . . ? C4 N1 C3 C4 -0.3(10) . . . 3_556 ? C1 C2 C3 N1 179.3(8) . . . . ? C1 C2 C3 C4 1.3(10) . . . 3_556 ? C3 N1 C4 C5 -179.8(8) . . . 3_556 ? C3 N1 C4 C3 0.3(10) . . . 3_556 ? C4 C5 C6 C1 -0.7(12) 3_556 . . . ? C2 C1 C6 C5 0.2(12) . . . . ? O1 C8 C9 C10 -84.9(8) . . . . ? O2 C8 C9 C10 99.6(8) . . . . ? O1 C8 C9 C12 91.6(10) . . . . ? O2 C8 C9 C12 -84.0(7) . . . . ? C12 C9 C10 C11 179.1(7) . . . . ? C8 C9 C10 C11 -4.8(10) . . . . ? C9 C10 C11 O3 -14.8(11) . . . . ? C9 C10 C11 O4 166.0(6) . . . . ? _refine_diff_density_max 0.096 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.028 #===END data_4c _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzopyrazine butanedioic acid ; _chemical_name_common 'Phenazine succinic acid' _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2, C4 H6 O4' _chemical_formula_sum 'C8 H7 N O2' _chemical_formula_weight 149.15 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 'P 1 21/n 1' 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 5.2792(4) _cell_length_b 9.0570(10) _cell_length_c 15.0540(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.141(7) _cell_angle_gamma 90.00 _cell_volume 710.65(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description kite _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9508 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1292 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 24.93 _reflns_number_total 1244 _reflns_number_gt 1070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 ' _computing_cell_refinement 'CAD4, SETANG ' _computing_data_reduction 'TEXSAN ' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'TEXSAN ' _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^)+(0.0694P)^2^+0.2246P] 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 0.079(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1244 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.211 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6146(3) 0.73948(16) 0.94714(10) 0.0424(4) Uani 1 1 d . . . H1O H 0.488(6) 0.780(3) 0.9672(18) 0.070(8) Uiso 1 1 d . . . O2 O 0.6644(3) 0.61573(18) 1.07591(10) 0.0517(5) Uani 1 1 d . . . N1 N 0.2066(3) 0.90559(17) 0.99105(10) 0.0328(4) Uani 1 1 d . . . C1 C 0.0560(4) 1.0529(3) 0.76526(14) 0.0472(6) Uani 1 1 d . . . H1 H 0.1122 1.0448 0.7100 0.056(3) Uiso 1 1 calc R . . C2 C 0.1710(4) 0.9724(2) 0.83560(13) 0.0411(5) Uani 1 1 d . . . H2 H 0.3048 0.9091 0.8283 0.056(3) Uiso 1 1 calc R . . C3 C 0.0890(3) 0.9839(2) 0.92094(12) 0.0314(5) Uani 1 1 d . . . C4 C 0.1211(3) 0.9196(2) 1.07016(12) 0.0317(5) Uani 1 1 d . . . C5 C 0.2377(4) 0.8374(2) 1.14617(13) 0.0395(5) Uani 1 1 d . . . H5 H 0.3744 0.7747 1.1414 0.056(3) Uiso 1 1 calc R . . C6 C 0.1498(4) 0.8503(3) 1.22558(14) 0.0458(6) Uani 1 1 d . . . H6 H 0.2254 0.7950 1.2748 0.056(3) Uiso 1 1 calc R . . C7 C 0.7241(3) 0.6368(2) 1.00350(12) 0.0316(5) Uani 1 1 d . . . C8 C 0.9270(4) 0.5524(2) 0.96586(13) 0.0356(5) Uani 1 1 d . . . H8A H 1.0466 0.6215 0.9459 0.055(5) Uiso 1 1 calc R . . H8B H 0.8475 0.4964 0.9139 0.055(5) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0423(8) 0.0419(8) 0.0455(9) 0.0060(6) 0.0149(7) 0.0169(6) O2 0.0565(9) 0.0563(10) 0.0480(9) 0.0117(7) 0.0263(7) 0.0235(7) N1 0.0302(8) 0.0321(8) 0.0373(9) -0.0034(7) 0.0088(7) 0.0033(6) C1 0.0503(12) 0.0611(14) 0.0327(10) -0.0037(10) 0.0140(9) 0.0060(10) C2 0.0402(11) 0.0475(12) 0.0377(10) -0.0040(9) 0.0128(9) 0.0087(9) C3 0.0293(9) 0.0322(9) 0.0331(10) -0.0043(8) 0.0062(7) 0.0001(7) C4 0.0290(9) 0.0314(9) 0.0355(10) -0.0055(8) 0.0076(7) -0.0011(8) C5 0.0360(10) 0.0396(11) 0.0430(11) 0.0003(9) 0.0069(8) 0.0075(8) C6 0.0485(12) 0.0502(12) 0.0382(11) 0.0043(9) 0.0055(9) 0.0090(10) C7 0.0290(9) 0.0286(9) 0.0382(10) -0.0001(8) 0.0083(8) 0.0022(7) C8 0.0351(10) 0.0337(10) 0.0403(11) 0.0009(8) 0.0128(8) 0.0067(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 O1 C7 1.327(2) . ? O2 C7 1.197(2) . ? N1 C3 1.339(2) . ? N1 C4 1.345(2) . ? C1 C2 1.348(3) . ? C1 C6 1.420(3) 3_577 ? C2 C3 1.423(3) . ? C3 C4 1.435(3) 3_577 ? C4 C5 1.421(3) . ? C4 C3 1.435(3) 3_577 ? C5 C6 1.354(3) . ? C6 C1 1.420(3) 3_577 ? C7 C8 1.499(2) . ? C8 C8 1.517(4) 3_767 ? 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 C3 N1 C4 117.96(15) . . ? C2 C1 C6 120.91(19) . 3_577 ? C1 C2 C3 120.40(18) . . ? N1 C3 C2 120.22(16) . . ? N1 C3 C4 121.14(17) . 3_577 ? C2 C3 C4 118.64(17) . 3_577 ? N1 C4 C5 119.99(16) . . ? N1 C4 C3 120.90(17) . 3_577 ? C5 C4 C3 119.11(17) . 3_577 ? C6 C5 C4 120.01(18) . . ? C5 C6 C1 120.92(19) . 3_577 ? O2 C7 O1 122.89(16) . . ? O2 C7 C8 124.75(17) . . ? O1 C7 C8 112.36(15) . . ? C7 C8 C8 112.34(19) . 3_767 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(3) 3_577 . . . ? C4 N1 C3 C2 -179.67(17) . . . . ? C4 N1 C3 C4 0.3(3) . . . 3_577 ? C1 C2 C3 N1 -178.89(19) . . . . ? C1 C2 C3 C4 1.2(3) . . . 3_577 ? C3 N1 C4 C5 179.22(17) . . . . ? C3 N1 C4 C3 -0.3(3) . . . 3_577 ? N1 C4 C5 C6 -179.28(19) . . . . ? C3 C4 C5 C6 0.2(3) 3_577 . . . ? C4 C5 C6 C1 -1.0(3) . . . 3_577 ? O2 C7 C8 C8 -6.7(3) . . . 3_767 ? O1 C7 C8 C8 173.4(2) . . . 3_767 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.206 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.057 #===END data_4d _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzopyrazine bis(pentanedioic acid) ; _chemical_name_common 'Phenazine bis(glutaric acid) _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2, 2(C5 H8 O4)' _chemical_formula_sum 'C11 H12 N O4' _chemical_formula_weight 222.22 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' '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6755(5) _cell_length_b 9.997(2) _cell_length_c 10.8660(10) _cell_angle_alpha 116.611(10) _cell_angle_beta 95.117(11) _cell_angle_gamma 90.044(10) _cell_volume 548.44(13) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description Prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 234 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2017 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.94 _reflns_number_total 1906 _reflns_number_gt 1069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 ' _computing_cell_refinement 'CAD4, SETANG ' _computing_data_reduction 'TEXSAN ' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'TEXSAN ' _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^)+(0.0721P)^2^+0.0038P] 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 1906 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1099 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0049(4) 0.4480(2) 0.7306(2) 0.0754(6) Uani 1 1 d . . . H1O H -0.126(6) 0.443(4) 0.776(4) 0.117(12) Uiso 1 1 d . . . O2 O -0.1572(3) 0.2478(3) 0.54841(19) 0.0933(7) Uani 1 1 d . . . O3 O 0.3107(3) 0.0445(2) 0.11471(19) 0.0731(6) Uani 1 1 d . . . O4 O 0.6338(3) 0.1778(3) 0.1288(2) 0.0815(6) Uani 1 1 d . . . H4O H 0.660(7) 0.095(4) 0.040(5) 0.135(14) Uiso 1 1 d . . . N1 N -0.3408(3) 0.4668(2) 0.8993(2) 0.0522(6) Uani 1 1 d . . . C1 C -0.5119(4) 0.3671(3) 0.8848(2) 0.0500(6) Uani 1 1 d . . . C2 C -0.5339(5) 0.2257(3) 0.7669(3) 0.0605(7) Uani 1 1 d . . . H2 H -0.4271 0.2019 0.7007 0.070(4) Uiso 1 1 calc R . . C3 C -0.7088(5) 0.1249(3) 0.7495(3) 0.0674(8) Uani 1 1 d . . . H3 H -0.7234 0.0331 0.6707 0.070(4) Uiso 1 1 calc R . . C4 C -0.8703(5) 0.1588(3) 0.8512(3) 0.0687(8) Uani 1 1 d . . . H4 H -0.9892 0.0883 0.8384 0.070(4) Uiso 1 1 calc R . . C5 C -0.8540(4) 0.2914(3) 0.9660(3) 0.0614(7) Uani 1 1 d . . . H5 H -0.9611 0.3114 1.0315 0.070(4) Uiso 1 1 calc R . . C6 C -0.6733(4) 0.4011(3) 0.9876(2) 0.0504(6) Uani 1 1 d . . . C7 C -0.0034(5) 0.3434(3) 0.6014(3) 0.0585(7) Uani 1 1 d . . . C8 C 0.2003(5) 0.3613(3) 0.5304(3) 0.0611(7) Uani 1 1 d . . . H8A H 0.3466 0.3619 0.5841 0.086(4) Uiso 1 1 calc R . . H8B H 0.1930 0.4578 0.5295 0.086(4) Uiso 1 1 calc R . . C9 C 0.2078(5) 0.2413(3) 0.3838(3) 0.0661(8) Uani 1 1 d . . . H9A H 0.2264 0.1449 0.3839 0.086(4) Uiso 1 1 calc R . . H9B H 0.0593 0.2366 0.3300 0.086(4) Uiso 1 1 calc R . . C10 C 0.4091(5) 0.2727(3) 0.3177(3) 0.0639(7) Uani 1 1 d . . . H10A H 0.3815 0.3654 0.3117 0.086(4) Uiso 1 1 calc R . . H10B H 0.5540 0.2881 0.3779 0.086(4) Uiso 1 1 calc R . . C11 C 0.4451(5) 0.1543(3) 0.1781(3) 0.0598(7) 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 O1 0.0768(14) 0.0719(13) 0.0623(13) 0.0128(10) 0.0295(10) -0.0081(10) O2 0.0709(13) 0.1273(18) 0.0584(12) 0.0197(12) 0.0138(10) -0.0369(13) O3 0.0692(12) 0.0808(13) 0.0615(12) 0.0225(10) 0.0212(9) -0.0185(10) O4 0.0666(13) 0.0912(14) 0.0713(13) 0.0191(12) 0.0287(10) -0.0217(11) N1 0.0460(12) 0.0585(13) 0.0509(12) 0.0223(11) 0.0122(9) -0.0006(10) C1 0.0454(14) 0.0549(15) 0.0506(14) 0.0239(12) 0.0091(10) 0.0007(11) C2 0.0611(16) 0.0588(17) 0.0566(16) 0.0198(14) 0.0153(12) 0.0019(13) C3 0.0729(19) 0.0535(16) 0.0661(18) 0.0176(14) 0.0108(14) -0.0048(14) C4 0.0623(18) 0.0651(18) 0.0751(19) 0.0279(17) 0.0089(14) -0.0140(14) C5 0.0524(15) 0.0658(17) 0.0666(18) 0.0290(15) 0.0136(12) -0.0075(13) C6 0.0459(14) 0.0561(16) 0.0507(14) 0.0247(13) 0.0093(10) -0.0007(11) C7 0.0513(15) 0.0750(19) 0.0491(16) 0.0270(15) 0.0096(12) -0.0003(14) C8 0.0544(15) 0.0700(17) 0.0573(16) 0.0264(14) 0.0100(12) -0.0049(13) C9 0.0569(16) 0.0797(19) 0.0558(16) 0.0238(15) 0.0140(12) -0.0070(14) C10 0.0554(15) 0.0733(18) 0.0602(17) 0.0260(15) 0.0143(12) -0.0062(13) C11 0.0532(15) 0.0716(18) 0.0596(16) 0.0326(15) 0.0133(12) -0.0038(13) _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 C7 1.319(3) . ? O2 C7 1.193(3) . ? O3 C11 1.220(3) . ? O4 C11 1.305(3) . ? N1 C6 1.338(3) 2_467 ? N1 C1 1.338(3) . ? C1 C2 1.416(3) . ? C1 C6 1.430(3) . ? C2 C3 1.353(3) . ? C3 C4 1.422(4) . ? C4 C5 1.349(4) . ? C5 C6 1.426(3) . ? C6 N1 1.338(3) 2_467 ? C7 C8 1.499(3) . ? C8 C9 1.509(4) . ? C9 C10 1.506(3) . ? C10 C11 1.481(4) . ? 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 N1 C1 117.9(2) 2_467 . ? N1 C1 C2 119.9(2) . . ? N1 C1 C6 120.8(2) . . ? C2 C1 C6 119.2(2) . . ? C3 C2 C1 120.6(2) . . ? C2 C3 C4 120.2(3) . . ? C5 C4 C3 121.1(3) . . ? C4 C5 C6 120.3(3) . . ? N1 C6 C5 120.2(2) 2_467 . ? N1 C6 C1 121.3(2) 2_467 . ? C5 C6 C1 118.5(2) . . ? O2 C7 O1 123.4(2) . . ? O2 C7 C8 124.8(2) . . ? O1 C7 C8 111.8(2) . . ? C7 C8 C9 114.7(2) . . ? C10 C9 C8 111.1(2) . . ? C11 C10 C9 115.3(2) . . ? O3 C11 O4 123.0(3) . . ? O3 C11 C10 123.1(2) . . ? O4 C11 C10 113.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C1 C2 -179.9(2) 2_467 . . . ? C6 N1 C1 C6 -0.3(4) 2_467 . . . ? N1 C1 C2 C3 -178.7(2) . . . . ? C6 C1 C2 C3 1.6(4) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 N1 179.2(2) . . . 2_467 ? C4 C5 C6 C1 0.2(4) . . . . ? N1 C1 C6 N1 0.3(4) . . . 2_467 ? C2 C1 C6 N1 180.0(2) . . . 2_467 ? N1 C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? O2 C7 C8 C9 -3.2(4) . . . . ? O1 C7 C8 C9 177.5(2) . . . . ? C7 C8 C9 C10 176.7(2) . . . . ? C8 C9 C10 C11 174.7(2) . . . . ? C9 C10 C11 O3 6.1(4) . . . . ? C9 C10 C11 O4 -173.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.130 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.050 #===END