# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Sergiy Rosokha' 'Jay K. Kochi' 'Jian Jiang Lu' 'Yakov P. Nizhnik' _publ_contact_author_name 'Sergiy Rosokha' _publ_contact_author_email SROSOKHA@UH.EDU _publ_section_title ; Trimorphism of Model Carcinogen 4-Nitroquinoline-N-oxide ; # Attachment 'formI.cif' data_yak03 _database_code_depnum_ccdc_archive 'CCDC 724991' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 N2 O3' _chemical_formula_sum 'C9 H6 N2 O3' _chemical_formula_weight 190.16 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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.435(2) _cell_length_b 6.1034(19) _cell_length_c 17.069(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.094(7) _cell_angle_gamma 90.00 _cell_volume 774.5(4) _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 block _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9752 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _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 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6874 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 30.45 _reflns_number_total 2289 _reflns_number_gt 1757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0097P)^2^+2.8510P] 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 2289 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.1963 _refine_ls_wR_factor_gt 0.1895 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 0.0530(4) -0.4367(4) 0.12135(15) 0.0316(6) Uani 1 1 d . . . O2 O 0.3463(4) 0.4329(4) 0.24985(14) 0.0341(6) Uani 1 1 d . . . O3 O 0.4788(4) 0.4488(5) 0.13767(16) 0.0378(7) Uani 1 1 d . . . N1 N 0.1261(4) -0.2476(5) 0.13357(16) 0.0234(6) Uani 1 1 d . . . N2 N 0.3762(4) 0.3599(5) 0.18357(17) 0.0275(6) Uani 1 1 d . . . C1 C 0.1396(5) -0.1683(6) 0.20669(19) 0.0268(7) Uani 1 1 d . . . H1 H 0.0929 -0.2510 0.2492 0.032 Uiso 1 1 calc R . . C2 C 0.2206(5) 0.0320(6) 0.22118(19) 0.0263(7) Uani 1 1 d . . . H2 H 0.2296 0.0842 0.2735 0.032 Uiso 1 1 calc R . . C3 C 0.2874(4) 0.1548(5) 0.16149(19) 0.0237(6) Uani 1 1 d . . . C4 C 0.2720(4) 0.0847(5) 0.08202(18) 0.0214(6) Uani 1 1 d . . . C5 C 0.3242(5) 0.2033(5) 0.01423(19) 0.0256(7) Uani 1 1 d . . . H5 H 0.3767 0.3444 0.0197 0.031 Uiso 1 1 calc R . . C6 C 0.2998(5) 0.1164(6) -0.05891(19) 0.0280(7) Uani 1 1 d . . . H6 H 0.3346 0.1991 -0.1035 0.034 Uiso 1 1 calc R . . C7 C 0.2242(5) -0.0931(6) -0.06940(19) 0.0278(7) Uani 1 1 d . . . H7 H 0.2117 -0.1519 -0.1206 0.033 Uiso 1 1 calc R . . C8 C 0.1685(5) -0.2123(6) -0.00580(19) 0.0258(7) Uani 1 1 d . . . H8 H 0.1157 -0.3529 -0.0125 0.031 Uiso 1 1 calc R . . C9 C 0.1910(4) -0.1231(5) 0.06930(18) 0.0220(6) 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 0.0372(15) 0.0232(12) 0.0344(13) 0.0009(10) 0.0001(11) -0.0089(10) O2 0.0484(17) 0.0271(13) 0.0268(12) -0.0080(10) -0.0064(11) 0.0007(12) O3 0.0390(16) 0.0359(15) 0.0385(14) -0.0037(12) 0.0050(12) -0.0144(12) N1 0.0243(14) 0.0201(12) 0.0258(13) 0.0003(10) 0.0003(11) -0.0008(10) N2 0.0288(15) 0.0231(14) 0.0306(14) -0.0007(11) -0.0055(12) -0.0003(11) C1 0.0284(17) 0.0287(17) 0.0232(15) 0.0040(13) 0.0013(13) 0.0008(13) C2 0.0272(17) 0.0289(17) 0.0227(14) -0.0027(13) -0.0001(13) 0.0026(14) C3 0.0224(15) 0.0216(15) 0.0270(15) -0.0031(12) -0.0017(12) -0.0001(12) C4 0.0199(15) 0.0216(15) 0.0228(14) -0.0006(11) 0.0000(11) 0.0048(11) C5 0.0267(17) 0.0206(15) 0.0294(16) 0.0029(13) 0.0020(13) -0.0013(12) C6 0.0281(18) 0.0309(17) 0.0249(15) 0.0051(13) 0.0032(13) 0.0024(14) C7 0.0293(18) 0.0312(18) 0.0231(15) -0.0039(13) -0.0006(13) 0.0046(14) C8 0.0271(17) 0.0233(16) 0.0269(15) -0.0025(13) -0.0037(13) 0.0019(13) C9 0.0224(15) 0.0212(14) 0.0223(14) 0.0020(12) 0.0003(11) 0.0032(12) _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 N1 1.293(4) . ? O2 N2 1.236(4) . ? O3 N2 1.222(4) . ? N1 C1 1.342(4) . ? N1 C9 1.420(4) . ? N2 C3 1.464(4) . ? C1 C2 1.385(5) . ? C1 H1 0.9500 . ? C2 C3 1.360(5) . ? C2 H2 0.9500 . ? C3 C4 1.427(4) . ? C4 C5 1.419(4) . ? C4 C9 1.420(4) . ? C5 C6 1.368(5) . ? C5 H5 0.9500 . ? C6 C7 1.408(5) . ? C6 H6 0.9500 . ? C7 C8 1.371(5) . ? C7 H7 0.9500 . ? C8 C9 1.403(4) . ? C8 H8 0.9500 . ? 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 O1 N1 C1 120.2(3) . . ? O1 N1 C9 119.8(3) . . ? C1 N1 C9 120.1(3) . . ? O3 N2 O2 122.7(3) . . ? O3 N2 C3 119.8(3) . . ? O2 N2 C3 117.5(3) . . ? N1 C1 C2 121.1(3) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 N2 116.3(3) . . ? C4 C3 N2 122.4(3) . . ? C5 C4 C9 116.5(3) . . ? C5 C4 C3 126.9(3) . . ? C9 C4 C3 116.5(3) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 118.8(3) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C8 C9 N1 117.3(3) . . ? C8 C9 C4 122.4(3) . . ? N1 C9 C4 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 29.80 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.353 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.082 # Attachment 'formII.cif' data_yak13 _database_code_depnum_ccdc_archive 'CCDC 724992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 N2 O3' _chemical_formula_sum 'C9 H6 N2 O3' _chemical_formula_weight 190.16 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 5.0709(10) _cell_length_b 6.1246(12) _cell_length_c 25.500(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 792.0(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 plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _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 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5994 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 30.60 _reflns_number_total 2335 _reflns_number_gt 1696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0376P)^2^+0.0972P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 2335 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 -0.2435(3) -0.3112(2) 0.10055(7) 0.0495(5) Uani 1 1 d . . . O3 O 0.1494(3) 0.5704(3) 0.19597(6) 0.0470(5) Uani 1 1 d . . . O2 O -0.2358(3) 0.5332(3) 0.23031(7) 0.0459(4) Uani 1 1 d . . . N1 N -0.2020(4) -0.1245(3) 0.12238(8) 0.0359(5) Uani 1 1 d . . . N2 N -0.0608(3) 0.4728(3) 0.20042(7) 0.0330(4) Uani 1 1 d . . . C1 C -0.3497(4) -0.0566(4) 0.16264(9) 0.0369(5) Uani 1 1 d . . . H1 H -0.4899 -0.1464 0.1747 0.044 Uiso 1 1 calc R . . C2 C -0.3034(4) 0.1409(4) 0.18717(8) 0.0319(5) Uani 1 1 d . . . H2 H -0.4108 0.1849 0.2158 0.038 Uiso 1 1 calc R . . C3 C -0.1036(4) 0.2729(3) 0.17035(8) 0.0260(4) Uani 1 1 d . . . C4 C 0.0557(4) 0.2143(3) 0.12652(8) 0.0259(5) Uani 1 1 d . . . C5 C 0.2576(4) 0.3407(3) 0.10330(8) 0.0291(5) Uani 1 1 d . . . H5 H 0.2968 0.4808 0.1173 0.035 Uiso 1 1 calc R . . C6 C 0.3977(4) 0.2660(4) 0.06120(8) 0.0359(5) Uani 1 1 d . . . H6 H 0.5324 0.3545 0.0464 0.043 Uiso 1 1 calc R . . C7 C 0.3450(4) 0.0611(4) 0.03963(8) 0.0402(6) Uani 1 1 d . . . H7 H 0.4452 0.0103 0.0106 0.048 Uiso 1 1 calc R . . C8 C 0.1500(4) -0.0662(4) 0.06011(9) 0.0380(5) Uani 1 1 d . . . H8 H 0.1138 -0.2056 0.0454 0.046 Uiso 1 1 calc R . . C9 C 0.0033(4) 0.0094(3) 0.10295(9) 0.0289(5) 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 0.0508(10) 0.0242(9) 0.0734(12) -0.0043(8) -0.0169(10) -0.0069(8) O3 0.0405(9) 0.0535(11) 0.0471(9) -0.0155(9) 0.0012(8) -0.0161(8) O2 0.0429(9) 0.0498(11) 0.0450(9) -0.0092(8) 0.0088(8) 0.0109(9) N1 0.0320(9) 0.0260(10) 0.0495(12) 0.0029(9) -0.0131(8) -0.0020(8) N2 0.0326(9) 0.0358(11) 0.0306(9) 0.0013(8) -0.0019(8) 0.0032(8) C1 0.0255(10) 0.0379(14) 0.0473(13) 0.0142(12) -0.0033(10) -0.0045(10) C2 0.0250(10) 0.0385(13) 0.0321(12) 0.0094(10) -0.0015(8) 0.0009(9) C3 0.0233(9) 0.0268(12) 0.0279(10) 0.0028(9) -0.0037(8) 0.0014(8) C4 0.0231(9) 0.0281(12) 0.0265(10) 0.0033(9) -0.0051(8) 0.0019(9) C5 0.0275(10) 0.0299(11) 0.0300(11) 0.0038(9) -0.0044(9) -0.0035(9) C6 0.0313(11) 0.0441(15) 0.0322(11) 0.0066(11) 0.0018(10) 0.0036(10) C7 0.0398(12) 0.0508(16) 0.0300(11) -0.0020(11) 0.0019(10) 0.0123(11) C8 0.0425(12) 0.0320(13) 0.0396(12) -0.0088(11) -0.0108(11) 0.0079(10) C9 0.0272(10) 0.0263(12) 0.0331(11) 0.0017(10) -0.0095(8) 0.0019(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 O1 N1 1.289(2) . ? O3 N2 1.227(2) . ? O2 N2 1.227(2) . ? N1 C1 1.337(3) . ? N1 C9 1.415(3) . ? N2 C3 1.461(3) . ? C1 C2 1.382(3) . ? C1 H1 0.9500 . ? C2 C3 1.365(3) . ? C2 H2 0.9500 . ? C3 C4 1.425(3) . ? C4 C5 1.414(3) . ? C4 C9 1.417(3) . ? C5 C6 1.366(3) . ? C5 H5 0.9500 . ? C6 C7 1.396(3) . ? C6 H6 0.9500 . ? C7 C8 1.363(3) . ? C7 H7 0.9500 . ? C8 C9 1.400(3) . ? C8 H8 0.9500 . ? 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 O1 N1 C1 121.1(2) . . ? O1 N1 C9 118.9(2) . . ? C1 N1 C9 120.05(19) . . ? O2 N2 O3 122.62(19) . . ? O2 N2 C3 118.10(17) . . ? O3 N2 C3 119.25(18) . . ? N1 C1 C2 121.6(2) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C3 C2 C1 120.2(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 121.2(2) . . ? C2 C3 N2 116.22(19) . . ? C4 C3 N2 122.57(17) . . ? C5 C4 C9 116.31(19) . . ? C5 C4 C3 126.96(19) . . ? C9 C4 C3 116.71(19) . . ? C6 C5 C4 121.5(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 120.8(2) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.1(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 N1 118.2(2) . . ? C8 C9 C4 121.6(2) . . ? N1 C9 C4 120.18(19) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.244 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.053