# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Ashwini Nangia' 'Roland Boese' 'Michael T. Kirchner' 'V. S. Senthil Kumar' _publ_contact_author_name 'Prof Ashwini Nangia' _publ_contact_author_address ; Prof Ashwini Nangia School of Chemistry University of Hyderabad Hyderabad 500 046 INDIA ; _publ_contact_author_email ANSC@UOHYD.ERNET.IN _publ_section_title ; Supramolecular synthesis of brick wall and honeycomb networks from T-shaped molecule 5-nitrosalicylic acid ; data_MNSA _database_code_CSD 198782 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Nitrosalicylic acid ; _chemical_name_common '5-Nitrosalicylic acid' _chemical_melting_point '501 K' _chemical_formula_moiety ? _chemical_formula_sum 'C7 H5 N O5' _chemical_formula_weight 183.12 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 5.2010(7) _cell_length_b 8.8753(13) _cell_length_c 9.2841(13) _cell_angle_alpha 62.449(2) _cell_angle_beta 75.388(2) _cell_angle_gamma 81.657(3) _cell_volume 367.47(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3097 _cell_measurement_theta_min 2.531 _cell_measurement_theta_max 28.212 _exptl_crystal_description block _exptl_crystal_colour 'brown t' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.887195 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4525 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1791 _reflns_number_gt 1565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1979-2000)' _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^)+(0.1448P)^2^+0.0067P] 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 1791 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1802 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4686(2) 0.27889(13) 0.57106(13) 0.0493(3) Uani 1 1 d . . . O1 O 0.30664(18) 0.32653(12) -0.01865(11) 0.0539(3) Uani 1 1 d . . . H1 H 0.4405 0.2601 -0.0545 0.081 Uiso 1 1 d R . . O2 O 0.73707(19) 0.12891(12) -0.02281(11) 0.0552(3) Uani 1 1 d . . . O3 O 0.92365(17) 0.01343(11) 0.19948(10) 0.0525(3) Uani 1 1 d . . . H2 H 1.0339 -0.0326 0.1437 0.079 Uiso 1 1 d R . . O4 O 0.6544(2) 0.19121(16) 0.62906(14) 0.0728(4) Uani 1 1 d . . . O5 O 0.3121(2) 0.35707(13) 0.63743(12) 0.0642(3) Uani 1 1 d . . . C1 C 0.3558(2) 0.30977(14) 0.12340(14) 0.0425(3) Uani 1 1 d . . . C2 C 0.5655(2) 0.20810(13) 0.19541(14) 0.0399(3) Uani 1 1 d . . . C3 C 0.6013(2) 0.19789(14) 0.34390(14) 0.0411(3) Uani 1 1 d . . . H3 H 0.7389 0.1306 0.3929 0.049 Uiso 1 1 d R . . C4 C 0.4291(2) 0.28931(14) 0.41685(14) 0.0420(3) Uani 1 1 d . . . C5 C 0.2219(2) 0.39069(16) 0.34659(15) 0.0481(3) Uani 1 1 d . . . H5 H 0.1091 0.4518 0.3974 0.058 Uiso 1 1 d R . . C6 C 0.1842(2) 0.40057(16) 0.20126(16) 0.0487(3) Uani 1 1 d . . . H6 H 0.0447 0.4677 0.1543 0.058 Uiso 1 1 d R . . C7 C 0.7504(2) 0.11327(14) 0.11419(15) 0.0430(3) 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 N1 0.0574(6) 0.0550(6) 0.0420(6) -0.0281(4) -0.0119(4) 0.0051(4) O1 0.0533(5) 0.0718(6) 0.0464(5) -0.0344(4) -0.0204(4) 0.0156(4) O2 0.0599(6) 0.0702(6) 0.0482(5) -0.0395(5) -0.0193(4) 0.0214(4) O3 0.0559(5) 0.0606(5) 0.0476(5) -0.0331(4) -0.0173(4) 0.0221(4) O4 0.0814(7) 0.0971(8) 0.0598(7) -0.0497(6) -0.0380(5) 0.0317(6) O5 0.0771(7) 0.0764(7) 0.0525(6) -0.0455(5) -0.0109(5) 0.0123(5) C1 0.0423(6) 0.0492(6) 0.0392(6) -0.0227(4) -0.0112(4) 0.0046(4) C2 0.0419(6) 0.0432(6) 0.0381(6) -0.0233(4) -0.0083(4) 0.0060(4) C3 0.0426(6) 0.0445(6) 0.0396(6) -0.0225(4) -0.0118(4) 0.0079(4) C4 0.0465(6) 0.0459(6) 0.0367(6) -0.0235(4) -0.0072(4) 0.0047(4) C5 0.0470(6) 0.0551(6) 0.0468(7) -0.0307(5) -0.0083(5) 0.0106(5) C6 0.0420(6) 0.0581(7) 0.0492(7) -0.0284(5) -0.0146(5) 0.0141(5) C7 0.0450(6) 0.0467(6) 0.0421(6) -0.0251(4) -0.0110(4) 0.0068(4) _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 N1 O4 1.2190(14) . ? N1 O5 1.2257(13) . ? N1 C4 1.4564(15) . ? O1 C1 1.3432(14) . ? O2 C7 1.2330(14) . ? O3 C7 1.3052(14) . ? C1 C6 1.4046(17) . ? C1 C2 1.4053(16) . ? C2 C3 1.3974(15) . ? C2 C7 1.4792(15) . ? C3 C4 1.3822(14) . ? C4 C5 1.3880(17) . ? C5 C6 1.3733(17) . ? 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 O4 N1 O5 123.06(11) . . ? O4 N1 C4 118.38(10) . . ? O5 N1 C4 118.56(10) . . ? O1 C1 C6 116.64(11) . . ? O1 C1 C2 123.69(10) . . ? C6 C1 C2 119.67(11) . . ? C3 C2 C1 119.77(10) . . ? C3 C2 C7 119.74(10) . . ? C1 C2 C7 120.48(10) . . ? C4 C3 C2 119.00(11) . . ? C3 C4 C5 121.76(11) . . ? C3 C4 N1 118.70(11) . . ? C5 C4 N1 119.54(10) . . ? C6 C5 C4 119.63(10) . . ? C5 C6 C1 120.17(11) . . ? O2 C7 O3 123.85(10) . . ? O2 C7 C2 121.57(11) . . ? O3 C7 C2 114.59(10) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.713 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.068 data_mnsa.dioxane _database_code_CSD 198783 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dioxane solvate of 5-Nitrosalicylic acid ; _chemical_name_common ; Dioxane solvate of 5-Nitrosalicylic acid ; _chemical_melting_point '497 K' _chemical_formula_moiety "'C9 H9 N O6'" _chemical_formula_sum 'C9 H9 N O6' _chemical_formula_weight 227.17 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 P21/c 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 5.3656(11) _cell_length_b 22.995(5) _cell_length_c 7.9984(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.79(3) _cell_angle_gamma 90.00 _cell_volume 986.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 10 _exptl_crystal_description needle _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.131 _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 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2602 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2371 _reflns_number_gt 1359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Data Collection Software' _computing_cell_refinement 'CAD4 Data Collection Software' _computing_data_reduction 'XTAL 3.5' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1979-2000)' _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^)+(0.0302P)^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 SHELXL _refine_ls_extinction_coef 0.042(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2371 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 O6 O 0.3563(2) 0.46615(4) -0.11179(13) 0.0569(3) Uani 1 1 d . . . C9 C 0.3436(3) 0.45795(7) 0.06518(19) 0.0586(4) Uani 1 1 d . . . H9A H 0.3077 0.4175 0.0889 0.070 Uiso 1 1 calc R . . H9B H 0.2091 0.4813 0.1092 0.070 Uiso 1 1 calc R . . C8 C 0.4181(3) 0.52529(7) -0.1490(2) 0.0595(4) Uani 1 1 d . . . H8A H 0.2856 0.5507 -0.1115 0.071 Uiso 1 1 calc R . . H8B H 0.4332 0.5300 -0.2690 0.071 Uiso 1 1 calc R . . C6 C 1.2151(3) 0.31451(8) -0.6210(2) 0.0623(4) Uani 1 1 d . . . H6A H 1.3546 0.3223 -0.6849 0.075 Uiso 1 1 calc R . . C7 C 0.7385(3) 0.39727(7) -0.37573(19) 0.0569(4) Uani 1 1 d . . . O3 O 0.5516(2) 0.38110(5) -0.28179(14) 0.0629(3) Uani 1 1 d . . . C3 C 0.7984(3) 0.29155(6) -0.43295(16) 0.0483(4) Uani 1 1 d . . . H3A H 0.6581 0.2832 -0.3704 0.058 Uiso 1 1 calc R . . C2 C 0.8730(3) 0.34894(6) -0.45466(17) 0.0489(4) Uani 1 1 d . . . O1 O 1.1674(3) 0.41417(6) -0.57788(17) 0.0784(4) Uani 1 1 d . . . N1 N 0.8539(3) 0.18760(6) -0.47738(16) 0.0579(4) Uani 1 1 d . . . O5 O 0.9814(2) 0.14867(5) -0.53418(16) 0.0765(4) Uani 1 1 d . . . O2 O 0.7983(3) 0.44804(5) -0.39586(15) 0.0764(4) Uani 1 1 d . . . C4 C 0.9319(3) 0.24742(6) -0.50378(16) 0.0482(4) Uani 1 1 d . . . C5 C 1.1422(3) 0.25830(8) -0.59764(18) 0.0564(4) Uani 1 1 d . . . H5A H 1.2320 0.2278 -0.6438 0.068 Uiso 1 1 calc R . . C1 C 1.0837(3) 0.36026(7) -0.55060(19) 0.0572(4) Uani 1 1 d . . . O4 O 0.6637(3) 0.17882(5) -0.39996(19) 0.0891(5) Uani 1 1 d . . . H3B H 0.484(4) 0.4159(10) -0.234(3) 0.108(8) Uiso 1 1 d . . . H1 H 1.050(6) 0.4378(13) -0.517(4) 0.158(12) Uiso 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 O6 0.0645(7) 0.0480(6) 0.0585(6) -0.0079(5) 0.0102(5) -0.0104(5) C9 0.0674(11) 0.0482(8) 0.0607(9) -0.0011(7) 0.0177(8) -0.0142(8) C8 0.0705(11) 0.0475(8) 0.0608(9) 0.0068(7) 0.0072(8) -0.0011(8) C6 0.0559(10) 0.0786(12) 0.0528(9) 0.0071(8) 0.0133(8) -0.0065(9) C7 0.0722(11) 0.0528(9) 0.0458(8) -0.0006(7) 0.0009(8) -0.0027(8) O3 0.0745(8) 0.0553(7) 0.0593(7) -0.0085(5) 0.0145(6) 0.0008(6) C3 0.0529(9) 0.0553(9) 0.0369(7) -0.0002(6) 0.0064(6) -0.0032(7) C2 0.0568(9) 0.0520(9) 0.0380(7) 0.0020(6) 0.0028(6) -0.0040(7) O1 0.0907(10) 0.0645(8) 0.0804(9) 0.0146(6) 0.0196(8) -0.0204(7) N1 0.0659(9) 0.0529(8) 0.0551(8) -0.0017(6) 0.0032(7) 0.0003(7) O5 0.0795(9) 0.0574(7) 0.0927(9) -0.0049(6) 0.0024(7) 0.0162(7) O2 0.1033(11) 0.0507(7) 0.0756(8) -0.0011(5) 0.0147(7) -0.0069(7) C4 0.0531(9) 0.0519(8) 0.0397(7) 0.0010(6) 0.0017(6) -0.0015(7) C5 0.0538(9) 0.0674(10) 0.0483(8) -0.0018(7) 0.0065(7) 0.0064(8) C1 0.0646(10) 0.0619(10) 0.0454(8) 0.0073(7) 0.0038(7) -0.0083(8) O4 0.0992(11) 0.0614(8) 0.1078(11) -0.0057(7) 0.0464(9) -0.0160(7) _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 O6 C9 1.4305(18) . ? O6 C8 1.4319(18) . ? C9 C8 1.486(2) 3_665 ? C8 C9 1.486(2) 3_665 ? C6 C5 1.364(2) . ? C6 C1 1.390(2) . ? C7 O2 1.2221(18) . ? C7 O3 1.3150(19) . ? C7 C2 1.472(2) . ? C3 C4 1.369(2) . ? C3 C2 1.391(2) . ? C2 C1 1.400(2) . ? O1 C1 1.337(2) . ? N1 O5 1.2182(17) . ? N1 O4 1.2183(18) . ? N1 C4 1.454(2) . ? C4 C5 1.387(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O6 C8 110.19(11) . . ? O6 C9 C8 111.08(13) . 3_665 ? O6 C8 C9 110.64(13) . 3_665 ? C5 C6 C1 120.94(15) . . ? O2 C7 O3 123.30(16) . . ? O2 C7 C2 122.25(16) . . ? O3 C7 C2 114.45(14) . . ? C4 C3 C2 119.92(14) . . ? C3 C2 C1 118.74(14) . . ? C3 C2 C7 121.29(14) . . ? C1 C2 C7 119.95(14) . . ? O5 N1 O4 123.13(15) . . ? O5 N1 C4 118.49(14) . . ? O4 N1 C4 118.38(13) . . ? C3 C4 C5 121.63(14) . . ? C3 C4 N1 119.21(13) . . ? C5 C4 N1 119.15(14) . . ? C6 C5 C4 118.81(15) . . ? O1 C1 C6 117.53(15) . . ? O1 C1 C2 122.51(16) . . ? C6 C1 C2 119.95(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.134 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.030