# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 1999 # CCDC Number: 440/146 data_(1) _audit_creation_method SHELXL-97 _chemical_name_systematic ; Z,2-(2-bromophenylhydrazono)-3-oxobutanenitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 Br N3 O' _chemical_formula_sum 'C10 H8 Br N3 O' _chemical_formula_weight 266.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Br' 'Br' -0.2901 2.4595 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/ 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 11.263(2) _cell_length_b 6.863(2) _cell_length_c 14.267(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.010(10) _cell_angle_gamma 90.00 _cell_volume 1100.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 14 _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 3.713 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 1. _exptl_absorpt_process_details ; (North, Phillips & Mathews, 1968) ; _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2751 _diffrn_reflns_av_R_equivalents 0.011 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2643 _reflns_number_gt 1287 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'CAD4 Enraf-Nonius, 1994' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1994' _computing_data_reduction 'MolEN, Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; PARST (Nardelli, 1983, 1995); 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^)+(0.0363P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2643 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 Br Br 0.33357(3) 0.50919(6) -0.11949(2) 0.07093(16) Uani 1 1 d . . . O1 O 0.6769(2) 0.5516(4) -0.09344(16) 0.0784(8) Uani 1 1 d . . . N1 N 0.5405(2) 0.5412(4) -0.2476(2) 0.0522(7) Uani 1 1 d . . . N2 N 0.6376(2) 0.5307(4) -0.29193(17) 0.0523(7) Uani 1 1 d . . . N3 N 0.9178(3) 0.5081(8) -0.3459(3) 0.139(2) Uani 1 1 d . . . C1 C 0.7616(3) 0.5412(5) -0.1411(3) 0.0671(10) Uani 1 1 d . . . C2 C 0.7409(3) 0.5305(5) -0.2437(2) 0.0591(9) Uani 1 1 d . . . C3 C 0.8882(4) 0.5383(11) -0.0987(4) 0.0926(16) Uani 1 1 d . . . C4 C 0.8397(3) 0.5185(7) -0.3015(3) 0.0837(12) Uani 1 1 d . . . C5 C 0.4295(2) 0.5415(4) -0.2979(2) 0.0490(8) Uani 1 1 d . . . C6 C 0.3250(3) 0.5280(5) -0.2518(2) 0.0523(8) Uani 1 1 d . . . C7 C 0.2168(3) 0.5271(6) -0.3020(3) 0.0641(9) Uani 1 1 d . . . C8 C 0.2091(3) 0.5393(5) -0.3975(3) 0.0652(10) Uani 1 1 d . . . C9 C 0.3109(3) 0.5546(5) -0.4446(3) 0.0657(11) Uani 1 1 d . . . C10 C 0.4205(3) 0.5592(5) -0.3964(2) 0.0577(9) Uani 1 1 d . . . H1 H 0.544(2) 0.540(4) -0.195(2) 0.033(8) Uiso 1 1 d . . . H31 H 0.876(4) 0.559(6) -0.031(3) 0.113(16) Uiso 1 1 d . . . H32 H 0.931(4) 0.634(7) -0.120(3) 0.13(2) Uiso 1 1 d . . . H33 H 0.937(5) 0.439(7) -0.126(4) 0.14(2) Uiso 1 1 d . . . H7 H 0.149(4) 0.523(5) -0.268(3) 0.084(12) Uiso 1 1 d . . . H8 H 0.144(3) 0.531(5) -0.433(2) 0.071(11) Uiso 1 1 d . . . H9 H 0.307(3) 0.560(5) -0.507(2) 0.064(10) Uiso 1 1 d . . . H10 H 0.486(3) 0.575(4) -0.4288(19) 0.044(8) 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 Br 0.0650(2) 0.0973(3) 0.05094(19) -0.0085(2) 0.00764(13) 0.0017(3) O1 0.0630(15) 0.118(2) 0.0519(13) 0.0067(14) -0.0101(11) -0.0079(15) N1 0.0462(14) 0.065(2) 0.0449(14) -0.0006(15) -0.0025(12) -0.0018(12) N2 0.0395(13) 0.0619(18) 0.0545(14) -0.0024(14) -0.0040(11) 0.0034(13) N3 0.0484(18) 0.262(6) 0.108(3) -0.016(4) 0.0049(19) 0.002(3) C1 0.055(2) 0.070(3) 0.073(2) 0.0073(19) -0.0191(18) -0.0032(18) C2 0.0442(17) 0.067(2) 0.065(2) 0.0027(18) -0.0070(14) -0.0005(17) C3 0.059(2) 0.129(5) 0.085(3) 0.009(4) -0.030(2) -0.005(3) C4 0.0406(17) 0.131(4) 0.078(2) -0.004(3) -0.0064(17) -0.002(3) C5 0.0418(15) 0.056(2) 0.0482(16) -0.0014(14) -0.0034(12) 0.0005(14) C6 0.0495(16) 0.060(2) 0.0471(15) -0.0034(16) 0.0005(12) -0.0019(16) C7 0.0406(16) 0.078(3) 0.074(2) -0.005(2) 0.0046(15) 0.0027(19) C8 0.0441(17) 0.078(3) 0.070(2) 0.001(2) -0.0172(16) 0.0038(18) C9 0.059(2) 0.084(3) 0.052(2) 0.0035(19) -0.0075(17) -0.0035(18) C10 0.0382(16) 0.078(3) 0.0560(19) 0.0012(17) -0.0013(14) -0.0023(16) _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 Br C6 1.888(3) . ? O1 C1 1.212(5) . ? N1 N2 1.303(3) . ? N1 C5 1.397(4) . ? N1 H1 0.75(3) . ? N2 C2 1.310(4) . ? N3 C4 1.122(5) . ? C1 C2 1.468(5) . ? C1 C3 1.509(5) . ? C2 C4 1.432(5) . ? C3 H31 1.00(4) . ? C3 H32 0.88(5) . ? C3 H33 0.98(5) . ? C5 C6 1.391(4) . ? C5 C10 1.407(4) . ? C6 C7 1.370(4) . ? C7 C8 1.362(5) . ? C7 H7 0.94(4) . ? C8 C9 1.373(5) . ? C8 H8 0.86(4) . ? C9 C10 1.370(5) . ? C9 H9 0.89(3) . ? C10 H10 0.90(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 N2 N1 C5 120.1(3) . . ? N2 N1 H1 120(2) . . ? C5 N1 H1 120(2) . . ? N1 N2 C2 119.3(3) . . ? O1 C1 C2 119.1(3) . . ? O1 C1 C3 122.3(4) . . ? C2 C1 C3 118.6(4) . . ? N2 C2 C4 113.2(3) . . ? N2 C2 C1 126.7(3) . . ? C4 C2 C1 120.1(3) . . ? C1 C3 H31 101(3) . . ? C1 C3 H32 112(3) . . ? H31 C3 H32 110(4) . . ? C1 C3 H33 113(3) . . ? H31 C3 H33 127(4) . . ? H32 C3 H33 93(5) . . ? N3 C4 C2 179.2(5) . . ? C6 C5 N1 120.9(3) . . ? C6 C5 C10 118.2(3) . . ? N1 C5 C10 120.9(3) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 Br 120.3(2) . . ? C5 C6 Br 119.4(2) . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 122(2) . . ? C6 C7 H7 117(2) . . ? C7 C8 C9 119.8(3) . . ? C7 C8 H8 126(2) . . ? C9 C8 H8 114(2) . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9 119(2) . . ? C8 C9 H9 121(2) . . ? C9 C10 C5 119.9(3) . . ? C9 C10 H10 119.0(18) . . ? C5 C10 H10 121.0(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.356 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.055 data_(2) _audit_creation_method SHELXL-97 _chemical_name_systematic ; Z,2-(2-methylphenylhydrazono)-3-oxobutanenitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O' _chemical_formula_sum 'C11 H11 N3 O' _chemical_formula_weight 201.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 7.565(2) _cell_length_b 14.423(2) _cell_length_c 19.793(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2159.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 13 _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.083 _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 'enraf-Nonis CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2580 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0992 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.95 _reflns_number_total 2580 _reflns_number_gt 940 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; PARST (Nardelli, 1983, 1985),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^)+(0.0511P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2580 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1945 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.886 _refine_ls_shift/su_max 0.004 _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 0.2974(3) -0.16235(12) 0.02368(9) 0.0748(6) Uani 1 1 d . . . N3 N 0.0461(4) 0.05033(18) -0.12809(12) 0.0862(8) Uani 1 1 d . . . N1 N 0.3487(3) 0.00352(15) 0.07074(10) 0.0520(5) Uani 1 1 d . . . N2 N 0.2706(3) 0.03518(15) 0.01695(10) 0.0547(6) Uani 1 1 d . . . C1 C 0.2193(3) -0.12596(18) -0.02388(13) 0.0586(7) Uani 1 1 d . . . C2 C 0.2099(3) -0.02550(18) -0.02801(11) 0.0516(6) Uani 1 1 d . . . C3 C 0.1325(6) -0.1826(3) -0.0776(2) 0.0822(10) Uani 1 1 d . . . C4 C 0.1200(4) 0.01770(19) -0.08385(13) 0.0632(7) Uani 1 1 d . . . C5 C 0.4068(3) 0.06423(16) 0.12157(12) 0.0504(6) Uani 1 1 d . . . C6 C 0.4820(3) 0.02506(17) 0.17927(12) 0.0559(7) Uani 1 1 d . . . C7 C 0.5418(4) 0.0856(2) 0.22888(15) 0.0703(8) Uani 1 1 d . . . C8 C 0.5262(4) 0.1787(2) 0.22239(17) 0.0772(9) Uani 1 1 d . . . C9 C 0.4497(4) 0.2167(2) 0.16579(16) 0.0727(9) Uani 1 1 d . . . C10 C 0.3905(4) 0.15922(19) 0.11503(14) 0.0598(7) Uani 1 1 d . . . C11 C 0.4965(6) -0.0781(2) 0.1882(2) 0.0803(10) Uani 1 1 d . . . H1 H 0.355(3) -0.0648(19) 0.0727(12) 0.076(8) Uiso 1 1 d . . . H31 H 0.154(5) -0.243(3) -0.0684(17) 0.144(16) Uiso 1 1 d . . . H32 H 0.023(5) -0.174(3) -0.080(2) 0.15(2) Uiso 1 1 d . . . H33 H 0.171(5) -0.162(3) -0.1263(19) 0.149(14) Uiso 1 1 d . . . H7 H 0.590(4) 0.056(2) 0.2684(16) 0.100(11) Uiso 1 1 d . . . H8 H 0.566(3) 0.2188(18) 0.2578(14) 0.080(9) Uiso 1 1 d . . . H9 H 0.440(3) 0.287(2) 0.1605(12) 0.082(9) Uiso 1 1 d . . . H10 H 0.344(3) 0.1848(16) 0.0727(12) 0.065(7) Uiso 1 1 d . . . H111 H 0.541(4) -0.091(2) 0.2304(15) 0.099(11) Uiso 1 1 d . . . H112 H 0.386(5) -0.108(2) 0.1843(15) 0.118(14) Uiso 1 1 d . . . H113 H 0.561(4) -0.105(2) 0.1514(17) 0.110(13) 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 O1 0.0867(14) 0.0589(11) 0.0788(12) 0.0071(10) -0.0063(11) 0.0011(11) N3 0.100(2) 0.0916(19) 0.0673(17) 0.0074(14) -0.0121(15) 0.0113(16) N1 0.0531(12) 0.0494(13) 0.0537(12) 0.0064(11) 0.0018(10) 0.0015(10) N2 0.0492(12) 0.0612(13) 0.0537(11) 0.0052(11) 0.0046(11) 0.0009(10) C1 0.0527(16) 0.0578(17) 0.0652(16) 0.0015(13) 0.0082(14) -0.0036(14) C2 0.0442(15) 0.0583(17) 0.0524(14) 0.0037(13) 0.0065(12) 0.0011(12) C3 0.083(3) 0.075(3) 0.088(3) -0.015(2) -0.007(2) -0.012(2) C4 0.0609(17) 0.0690(18) 0.0597(17) 0.0018(15) 0.0057(15) 0.0009(15) C5 0.0457(14) 0.0537(16) 0.0518(15) 0.0025(12) 0.0053(12) 0.0001(12) C6 0.0530(15) 0.0559(16) 0.0587(16) 0.0038(14) 0.0051(13) 0.0019(14) C7 0.070(2) 0.077(2) 0.0638(19) 0.0000(16) -0.0026(16) 0.0007(16) C8 0.080(2) 0.074(2) 0.078(2) -0.0124(19) -0.0047(19) -0.0078(18) C9 0.077(2) 0.0531(18) 0.088(2) -0.0071(17) 0.0080(18) -0.0045(16) C10 0.0594(17) 0.0534(17) 0.0667(18) 0.0062(15) 0.0039(15) 0.0044(14) C11 0.104(3) 0.068(2) 0.069(2) 0.0128(18) -0.011(2) 0.006(2) _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 1.229(3) . ? N3 C4 1.141(3) . ? N1 N2 1.300(2) . ? N1 C5 1.404(3) . ? N1 H1 0.99(3) . ? N2 C2 1.330(3) . ? C1 C2 1.453(3) . ? C1 C3 1.493(4) . ? C2 C4 1.439(4) . ? C3 H31 0.90(4) . ? C3 H32 0.84(4) . ? C3 H33 1.05(4) . ? C5 C10 1.382(3) . ? C5 C6 1.396(3) . ? C6 C7 1.390(4) . ? C6 C11 1.502(4) . ? C7 C8 1.355(4) . ? C7 H7 0.96(3) . ? C8 C9 1.375(4) . ? C8 H8 0.96(3) . ? C9 C10 1.378(4) . ? C9 H9 1.02(3) . ? C10 H10 0.98(2) . ? C11 H111 0.92(3) . ? C11 H112 0.94(4) . ? C11 H113 0.96(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 N2 N1 C5 120.6(2) . . ? N2 N1 H1 114.0(14) . . ? C5 N1 H1 125.3(14) . . ? N1 N2 C2 118.3(2) . . ? O1 C1 C2 119.5(2) . . ? O1 C1 C3 121.6(3) . . ? C2 C1 C3 118.9(3) . . ? N2 C2 C4 113.1(2) . . ? N2 C2 C1 127.0(2) . . ? C4 C2 C1 119.9(3) . . ? C1 C3 H31 108(2) . . ? C1 C3 H32 113(3) . . ? H31 C3 H32 110(4) . . ? C1 C3 H33 112(2) . . ? H31 C3 H33 114(3) . . ? H32 C3 H33 100(4) . . ? N3 C4 C2 178.5(3) . . ? C10 C5 C6 121.0(2) . . ? C10 C5 N1 121.6(2) . . ? C6 C5 N1 117.5(2) . . ? C7 C6 C5 117.2(2) . . ? C7 C6 C11 121.0(3) . . ? C5 C6 C11 121.8(3) . . ? C8 C7 C6 121.8(3) . . ? C8 C7 H7 123.3(18) . . ? C6 C7 H7 114.9(18) . . ? C7 C8 C9 120.6(3) . . ? C7 C8 H8 120.2(15) . . ? C9 C8 H8 119.2(15) . . ? C8 C9 C10 119.4(3) . . ? C8 C9 H9 120.6(15) . . ? C10 C9 H9 120.0(15) . . ? C9 C10 C5 120.0(3) . . ? C9 C10 H10 120.9(14) . . ? C5 C10 H10 119.0(14) . . ? C6 C11 H111 109.3(19) . . ? C6 C11 H112 112(2) . . ? H111 C11 H112 108(3) . . ? C6 C11 H113 110.7(19) . . ? H111 C11 H113 115(3) . . ? H112 C11 H113 102(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.153 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.041 data_(3) _audit_creation_method SHELXL-97 _chemical_name_systematic ; E,Methyl-2-(methoxyphenylhydrazono)-3-oxobutanoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2 O4' _chemical_formula_sum 'C12 H14 N2 O4' _chemical_formula_weight 250.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/n ' 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 12.720(2) _cell_length_b 6.9540(10) _cell_length_c 14.783(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.610(10) _cell_angle_gamma 90.00 _cell_volume 1215.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description 'prism' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.104 _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 'Enraf Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2752 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 26.97 _reflns_number_total 2633 _reflns_number_gt 1711 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1994' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1994' _computing_data_reduction 'MolEN, fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; PARST (Nardelli, 1983, 1995), 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^)+(0.0844P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2633 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.005 _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 0.21651(12) -0.1996(3) 0.07358(11) 0.0645(5) Uani 1 1 d . . . O2 O -0.10350(14) -0.1921(3) 0.08838(11) 0.0681(5) Uani 1 1 d . . . O3 O -0.16935(11) -0.3308(2) -0.05707(10) 0.0555(4) Uani 1 1 d . . . O4 O 0.29323(10) -0.3212(2) -0.13844(9) 0.0424(3) Uani 1 1 d . . . N1 N 0.10606(13) -0.2807(2) -0.10536(11) 0.0373(4) Uani 1 1 d . . . N2 N 0.01580(12) -0.2812(2) -0.08384(11) 0.0363(4) Uani 1 1 d . . . C1 C 0.12836(17) -0.2132(3) 0.08855(14) 0.0462(5) Uani 1 1 d . . . C2 C 0.02264(15) -0.2488(3) 0.00604(13) 0.0383(4) Uani 1 1 d . . . C3 C 0.1318(3) -0.1989(7) 0.19013(18) 0.0797(9) Uani 1 1 d . . . C4 C -0.08766(16) -0.2523(3) 0.01850(14) 0.0418(5) Uani 1 1 d . . . C5 C -0.2806(2) -0.3301(6) -0.0520(2) 0.0652(7) Uani 1 1 d . . . C6 C 0.09611(14) -0.3084(3) -0.20176(13) 0.0333(4) Uani 1 1 d . . . C7 C -0.00684(15) -0.3139(3) -0.27837(14) 0.0389(4) Uani 1 1 d . . . C8 C -0.01072(16) -0.3384(3) -0.37208(14) 0.0414(5) Uani 1 1 d . . . C9 C 0.08794(16) -0.3560(3) -0.38893(14) 0.0415(5) Uani 1 1 d . . . C10 C 0.19201(16) -0.3499(3) -0.31325(14) 0.0386(4) Uani 1 1 d . . . C11 C 0.19678(14) -0.3277(2) -0.21931(12) 0.0329(4) Uani 1 1 d . . . C12 C 0.39730(17) -0.3413(3) -0.15279(18) 0.0480(5) Uani 1 1 d . . . H1 H 0.1710(19) -0.250(3) -0.0587(17) 0.048(6) Uiso 1 1 d . . . H31 H 0.090(3) -0.310(6) 0.204(3) 0.124(13) Uiso 1 1 d . . . H32 H 0.214(3) -0.205(5) 0.232(3) 0.114(11) Uiso 1 1 d . . . H33 H 0.100(3) -0.073(7) 0.207(3) 0.156(16) Uiso 1 1 d . . . H51 H -0.277(2) -0.381(4) 0.008(2) 0.083(8) Uiso 1 1 d . . . H52 H -0.323(2) -0.426(4) -0.102(2) 0.083(9) Uiso 1 1 d . . . H53 H -0.310(2) -0.200(4) -0.067(2) 0.079(9) Uiso 1 1 d . . . H7 H -0.0746(17) -0.296(3) -0.2659(14) 0.044(5) Uiso 1 1 d . . . H8 H -0.0864(18) -0.340(3) -0.4279(16) 0.055(6) Uiso 1 1 d . . . H9 H 0.0900(16) -0.373(3) -0.4521(15) 0.047(5) Uiso 1 1 d . . . H10 H 0.2571(16) -0.364(3) -0.3272(13) 0.036(5) Uiso 1 1 d . . . H121 H 0.412(2) -0.234(4) -0.1900(19) 0.070(7) Uiso 1 1 d . . . H122 H 0.453(2) -0.344(4) -0.0888(19) 0.067(7) Uiso 1 1 d . . . H123 H 0.4015(17) -0.467(4) -0.1842(15) 0.061(6) 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 O1 0.0402(8) 0.1053(13) 0.0465(8) -0.0113(8) 0.0143(6) -0.0112(8) O2 0.0617(10) 0.1012(13) 0.0573(9) -0.0208(9) 0.0407(8) -0.0051(9) O3 0.0354(7) 0.0928(11) 0.0450(8) -0.0084(8) 0.0226(6) 0.0004(7) O4 0.0296(6) 0.0584(8) 0.0404(7) -0.0018(6) 0.0142(5) -0.0005(6) N1 0.0313(8) 0.0507(9) 0.0342(8) -0.0041(7) 0.0173(7) -0.0033(7) N2 0.0353(8) 0.0422(8) 0.0374(8) 0.0006(7) 0.0205(6) 0.0018(6) C1 0.0461(11) 0.0549(12) 0.0386(10) -0.0032(9) 0.0168(9) 0.0007(9) C2 0.0421(11) 0.0423(10) 0.0356(9) -0.0009(8) 0.0200(8) 0.0023(8) C3 0.0606(16) 0.137(3) 0.0390(12) -0.0097(16) 0.0157(12) -0.0007(19) C4 0.0454(10) 0.0477(11) 0.0402(10) 0.0023(8) 0.0250(9) 0.0054(9) C5 0.0389(12) 0.108(2) 0.0570(15) 0.0058(16) 0.0273(11) 0.0069(14) C6 0.0343(9) 0.0355(9) 0.0353(9) -0.0009(7) 0.0191(7) -0.0007(7) C7 0.0317(9) 0.0454(10) 0.0429(10) -0.0024(8) 0.0178(8) -0.0003(8) C8 0.0376(10) 0.0489(11) 0.0371(10) -0.0023(9) 0.0131(8) -0.0038(8) C9 0.0482(11) 0.0483(11) 0.0312(9) -0.0030(8) 0.0183(8) -0.0015(9) C10 0.0398(10) 0.0410(10) 0.0441(10) -0.0009(8) 0.0263(8) -0.0001(8) C11 0.0306(9) 0.0360(9) 0.0354(9) 0.0010(7) 0.0159(7) -0.0010(7) C12 0.0313(10) 0.0540(13) 0.0601(14) -0.0105(11) 0.0186(10) -0.0013(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 C1 1.224(2) . ? O2 C4 1.198(2) . ? O3 C4 1.331(2) . ? O3 C5 1.445(2) . ? O4 C11 1.362(2) . ? O4 C12 1.423(2) . ? N1 N2 1.2993(19) . ? N1 C6 1.397(2) . ? N1 H1 0.89(2) . ? N2 C2 1.319(2) . ? C1 C2 1.466(3) . ? C1 C3 1.489(3) . ? C2 C4 1.481(2) . ? C3 H31 1.00(4) . ? C3 H32 1.01(4) . ? C3 H33 1.04(5) . ? C5 H51 0.93(3) . ? C5 H52 1.00(3) . ? C5 H53 0.97(3) . ? C6 C7 1.381(3) . ? C6 C11 1.403(2) . ? C7 C8 1.378(3) . ? C7 H7 0.95(2) . ? C8 C9 1.372(3) . ? C8 H8 1.01(2) . ? C9 C10 1.384(3) . ? C9 H9 0.95(2) . ? C10 C11 1.376(2) . ? C10 H10 0.929(19) . ? C12 H121 0.98(3) . ? C12 H122 0.95(3) . ? C12 H123 1.00(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 C4 O3 C5 115.62(17) . . ? C11 O4 C12 116.91(15) . . ? N2 N1 C6 119.55(15) . . ? N2 N1 H1 117.7(13) . . ? C6 N1 H1 122.4(13) . . ? N1 N2 C2 120.66(15) . . ? O1 C1 C2 118.90(17) . . ? O1 C1 C3 119.2(2) . . ? C2 C1 C3 121.84(19) . . ? N2 C2 C1 124.55(16) . . ? N2 C2 C4 114.12(16) . . ? C1 C2 C4 121.33(16) . . ? C1 C3 H31 109(2) . . ? C1 C3 H32 104.8(19) . . ? H31 C3 H32 111(3) . . ? C1 C3 H33 115(2) . . ? H31 C3 H33 108(3) . . ? H32 C3 H33 108(3) . . ? O2 C4 O3 122.66(18) . . ? O2 C4 C2 124.70(19) . . ? O3 C4 C2 112.64(15) . . ? O3 C5 H51 109.6(16) . . ? O3 C5 H52 103.0(14) . . ? H51 C5 H52 106(2) . . ? O3 C5 H53 106.8(16) . . ? H51 C5 H53 117(2) . . ? H52 C5 H53 113(2) . . ? C7 C6 N1 122.88(15) . . ? C7 C6 C11 120.00(15) . . ? N1 C6 C11 117.11(15) . . ? C8 C7 C6 119.99(16) . . ? C8 C7 H7 120.6(12) . . ? C6 C7 H7 119.3(12) . . ? C9 C8 C7 119.80(17) . . ? C9 C8 H8 120.6(12) . . ? C7 C8 H8 119.5(12) . . ? C8 C9 C10 121.13(17) . . ? C8 C9 H9 123.2(12) . . ? C10 C9 H9 115.7(12) . . ? C11 C10 C9 119.52(16) . . ? C11 C10 H10 121.6(11) . . ? C9 C10 H10 118.9(11) . . ? O4 C11 C10 125.45(15) . . ? O4 C11 C6 115.01(14) . . ? C10 C11 C6 119.54(16) . . ? O4 C12 H121 112.6(15) . . ? O4 C12 H122 104.0(14) . . ? H121 C12 H122 110(2) . . ? O4 C12 H123 111.6(12) . . ? H121 C12 H123 110.4(19) . . ? H122 C12 H123 107.5(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.207 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.044 data_(4) _audit_creation_method SHELXL-97 _chemical_name_systematic ; E,Methyl-2-(2-cyanophenylhydrazono)3-oxobutanoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 N3 O3' _chemical_formula_sum 'C12 H11 N3 O3' _chemical_formula_weight 245.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _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 8.3020(10) _cell_length_b 8.516(2) _cell_length_c 9.333(2) _cell_angle_alpha 99.50(2) _cell_angle_beta 97.06(2) _cell_angle_gamma 108.21(2) _cell_volume 607.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 13 _exptl_crystal_description 'prism' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.099 _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3093 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.50 _reflns_number_total 2511 _reflns_number_gt 1170 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ;PARST (Nardelli, 1983, 1995); 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^)+(0.1035P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2511 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1506 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.1989 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.002 _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 -0.3373(3) 0.1952(4) -0.0504(3) 0.0781(9) Uani 1 1 d . . . O2 O 0.0259(4) 0.5614(4) 0.2916(3) 0.0884(10) Uani 1 1 d . . . O3 O 0.2246(3) 0.4653(3) 0.2142(3) 0.0829(9) Uani 1 1 d . . . N1 N -0.0741(4) 0.1273(3) -0.1139(3) 0.0486(7) Uani 1 1 d . . . N2 N 0.0161(3) 0.2463(3) -0.0010(3) 0.0485(7) Uani 1 1 d . . . N3 N -0.4168(4) -0.1555(5) -0.3745(4) 0.0908(13) Uani 1 1 d . . . C1 C -0.2442(5) 0.3065(5) 0.0538(4) 0.0580(9) Uani 1 1 d . . . C2 C -0.0585(4) 0.3332(4) 0.0812(3) 0.0479(8) Uani 1 1 d . . . C3 C -0.3223(9) 0.4096(8) 0.1485(8) 0.0926(16) Uani 1 1 d . . . C4 C 0.0628(5) 0.4636(4) 0.2051(4) 0.0581(9) Uani 1 1 d . . . C5 C 0.3470(8) 0.5840(8) 0.3324(7) 0.0968(17) Uani 1 1 d . . . C6 C 0.0089(4) 0.0424(4) -0.2045(3) 0.0445(8) Uani 1 1 d . . . C7 C 0.1865(4) 0.0816(5) -0.1742(4) 0.0542(9) Uani 1 1 d . . . C8 C 0.2605(5) -0.0078(5) -0.2666(5) 0.0627(11) Uani 1 1 d . . . C9 C 0.1648(5) -0.1310(5) -0.3848(4) 0.0620(10) Uani 1 1 d . . . C10 C -0.0114(4) -0.1706(5) -0.4155(4) 0.0552(9) Uani 1 1 d . . . C11 C -0.0888(4) -0.0843(4) -0.3246(3) 0.0441(8) Uani 1 1 d . . . C12 C -0.2711(4) -0.1245(5) -0.3525(4) 0.0602(10) Uani 1 1 d . . . H1 H -0.184(5) 0.090(5) -0.140(4) 0.068(12) Uiso 1 1 d . . . H31 H -0.252(8) 0.448(9) 0.242(8) 0.16(3) Uiso 1 1 d . . . H32 H -0.442(7) 0.378(6) 0.111(5) 0.114(18) Uiso 1 1 d . . . H33 H -0.267(6) 0.523(7) 0.139(5) 0.12(2) Uiso 1 1 d . . . H51 H 0.447(8) 0.582(8) 0.322(7) 0.16(3) Uiso 1 1 d . . . H52 H 0.347(6) 0.697(6) 0.337(5) 0.104(17) Uiso 1 1 d . . . H53 H 0.305(6) 0.564(6) 0.438(6) 0.120(18) Uiso 1 1 d . . . H7 H 0.247(4) 0.158(3) -0.095(3) 0.029(7) Uiso 1 1 d . . . H8 H 0.373(5) 0.019(5) -0.242(4) 0.082(12) Uiso 1 1 d . . . H9 H 0.209(5) -0.187(5) -0.457(4) 0.074(11) Uiso 1 1 d . . . H10 H -0.081(4) -0.260(4) -0.503(3) 0.045(8) 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 O1 0.0542(15) 0.094(2) 0.0848(19) -0.0052(16) 0.0105(13) 0.0376(14) O2 0.101(2) 0.0829(19) 0.0788(18) -0.0226(15) 0.0106(16) 0.0505(17) O3 0.0616(17) 0.0825(19) 0.0831(19) -0.0231(15) 0.0032(14) 0.0193(14) N1 0.0411(16) 0.0520(17) 0.0536(17) 0.0004(14) 0.0096(14) 0.0225(14) N2 0.0536(16) 0.0455(15) 0.0462(15) 0.0025(13) 0.0079(13) 0.0210(13) N3 0.0460(19) 0.117(3) 0.097(3) -0.011(2) 0.0048(17) 0.0310(19) C1 0.061(2) 0.057(2) 0.065(2) 0.0087(19) 0.0166(19) 0.0327(19) C2 0.059(2) 0.0417(17) 0.0484(19) 0.0071(15) 0.0123(15) 0.0243(15) C3 0.089(4) 0.090(4) 0.103(4) -0.008(3) 0.028(4) 0.047(3) C4 0.072(3) 0.047(2) 0.054(2) 0.0087(17) 0.0112(18) 0.0204(18) C5 0.075(3) 0.091(4) 0.093(4) -0.026(3) -0.009(3) 0.017(3) C6 0.0434(18) 0.0461(18) 0.0512(19) 0.0124(15) 0.0159(15) 0.0216(15) C7 0.0427(19) 0.054(2) 0.061(2) 0.0017(18) 0.0063(17) 0.0161(16) C8 0.039(2) 0.071(3) 0.086(3) 0.014(2) 0.019(2) 0.0306(19) C9 0.065(2) 0.066(2) 0.067(3) 0.008(2) 0.025(2) 0.038(2) C10 0.058(2) 0.058(2) 0.048(2) 0.0008(17) 0.0080(17) 0.0229(18) C11 0.0381(16) 0.0502(19) 0.0452(18) 0.0027(15) 0.0074(14) 0.0209(15) C12 0.046(2) 0.069(2) 0.059(2) -0.0053(17) 0.0055(16) 0.0223(18) _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 1.223(4) . ? O2 C4 1.199(4) . ? O3 C4 1.331(4) . ? O3 C5 1.409(5) . ? N1 N2 1.295(3) . ? N1 C6 1.403(4) . ? N1 H1 0.85(4) . ? N2 C2 1.318(4) . ? N3 C12 1.139(4) . ? C1 C2 1.469(5) . ? C1 C3 1.487(5) . ? C2 C4 1.475(5) . ? C3 H31 0.93(7) . ? C3 H32 0.95(5) . ? C3 H33 0.95(5) . ? C5 H51 0.86(6) . ? C5 H52 0.96(5) . ? C5 H53 1.10(5) . ? C6 C11 1.381(4) . ? C6 C7 1.387(4) . ? C7 C8 1.380(5) . ? C7 H7 0.87(3) . ? C8 C9 1.353(5) . ? C8 H8 0.88(4) . ? C9 C10 1.376(5) . ? C9 H9 0.94(4) . ? C10 C11 1.378(4) . ? C10 H10 0.99(3) . ? C11 C12 1.423(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 C4 O3 C5 116.4(4) . . ? N2 N1 C6 119.7(3) . . ? N2 N1 H1 127(3) . . ? C6 N1 H1 113(3) . . ? N1 N2 C2 120.7(3) . . ? O1 C1 C2 118.5(3) . . ? O1 C1 C3 119.2(4) . . ? C2 C1 C3 122.3(4) . . ? N2 C2 C1 124.2(3) . . ? N2 C2 C4 113.6(3) . . ? C1 C2 C4 122.1(3) . . ? C1 C3 H31 107(4) . . ? C1 C3 H32 110(3) . . ? H31 C3 H32 136(5) . . ? C1 C3 H33 104(3) . . ? H31 C3 H33 83(4) . . ? H32 C3 H33 109(4) . . ? O2 C4 O3 121.0(4) . . ? O2 C4 C2 125.7(3) . . ? O3 C4 C2 113.3(3) . . ? O3 C5 H51 108(4) . . ? O3 C5 H52 113(3) . . ? H51 C5 H52 108(5) . . ? O3 C5 H53 109(3) . . ? H51 C5 H53 119(5) . . ? H52 C5 H53 99(4) . . ? C11 C6 C7 119.7(3) . . ? C11 C6 N1 119.1(3) . . ? C7 C6 N1 121.2(3) . . ? C8 C7 C6 118.4(4) . . ? C8 C7 H7 122.4(17) . . ? C6 C7 H7 119.1(18) . . ? C9 C8 C7 121.8(3) . . ? C9 C8 H8 123(3) . . ? C7 C8 H8 115(3) . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 125(2) . . ? C10 C9 H9 114(2) . . ? C9 C10 C11 119.3(3) . . ? C9 C10 H10 119.9(17) . . ? C11 C10 H10 120.8(17) . . ? C10 C11 C6 120.6(3) . . ? C10 C11 C12 120.5(3) . . ? C6 C11 C12 118.9(3) . . ? N3 C12 C11 179.5(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.281 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.054 data_(5) _audit_creation_method SHELXL-97 _chemical_name_systematic ; Z,Methyl-2-(4-cyanophenylhydrazono)-3-oxobutanoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 N3 O3' _chemical_formula_sum 'C12 H11 N3 O3' _chemical_formula_weight 245.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting ' orthorhombic' _symmetry_space_group_name_H-M 'P b c m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y-1/2, z' _cell_length_a 12.651(2) _cell_length_b 14.571(2) _cell_length_c 6.6490(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1225.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 14 _exptl_crystal_description 'prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.098 _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 'Enraf-nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1595 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.96 _reflns_number_total 1595 _reflns_number_gt 1056 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ' ORTEPII (Johnson, 1976)' _computing_publication_material ; PARST (Nardelli, 1983, 1995), 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^)+(0.0905P)^2^+0.2856P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1595 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1746 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.010 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 -0.00210(19) -0.02855(16) 0.2500 0.0940(10) Uani 1 2 d S . . O2 O 0.32642(16) -0.00329(13) 0.2500 0.0621(6) Uani 1 2 d S . . O3 O 0.19079(19) -0.09947(14) 0.2500 0.0787(8) Uani 1 2 d S . . N1 N 0.28194(17) 0.17200(15) 0.2500 0.0429(5) Uani 1 2 d S . . N2 N 0.18318(17) 0.14519(15) 0.2500 0.0451(5) Uani 1 2 d S . . N3 N 0.3997(3) 0.6233(2) 0.2500 0.0910(11) Uani 1 2 d S . . C1 C 0.0377(2) 0.0465(2) 0.2500 0.0634(9) Uani 1 2 d S . . C2 C 0.1544(2) 0.05958(19) 0.2500 0.0482(7) Uani 1 2 d S . . C3 C -0.0302(3) 0.1298(3) 0.2500 0.0984(18) Uani 1 2 d S . . C4 C 0.2318(2) -0.01601(18) 0.2500 0.0501(7) Uani 1 2 d S . . C5 C 0.2641(4) -0.1745(2) 0.2500 0.0874(14) Uani 1 2 d S . . C6 C 0.30480(18) 0.26610(16) 0.2500 0.0393(6) Uani 1 2 d S . . C7 C 0.22574(19) 0.33189(18) 0.2500 0.0425(6) Uani 1 2 d S . . C8 C 0.2516(2) 0.42246(18) 0.2500 0.0459(6) Uani 1 2 d S . . C9 C 0.3566(2) 0.45060(17) 0.2500 0.0454(6) Uani 1 2 d S . . C10 C 0.4361(2) 0.38445(19) 0.2500 0.0511(7) Uani 1 2 d S . . C11 C 0.4102(2) 0.29230(18) 0.2500 0.0469(7) Uani 1 2 d S . . C12 C 0.3820(2) 0.5465(2) 0.2500 0.0602(8) Uani 1 2 d S . . H1 H 0.326(3) 0.128(2) 0.2500 0.055(9) Uiso 1 2 d S . . H7 H 0.158(2) 0.3150(18) 0.2500 0.037(6) Uiso 1 2 d S . . H8 H 0.191(3) 0.465(2) 0.2500 0.055(8) Uiso 1 2 d S . . H10 H 0.511(3) 0.395(2) 0.2500 0.065(9) Uiso 1 2 d S . . H11 H 0.468(2) 0.242(2) 0.2500 0.051(7) Uiso 1 2 d S . . H31 H -0.012(4) 0.161(3) 0.143(7) 0.18(2) Uiso 1 1 d . . . H32 H -0.104(4) 0.121(3) 0.2500 0.088(12) Uiso 1 2 d S . . H51 H 0.308(3) -0.167(3) 0.123(7) 0.149(15) Uiso 1 1 d . . . H52 H 0.222(4) -0.224(4) 0.2500 0.120 Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0512(12) 0.0588(13) 0.172(3) 0.000 0.000 -0.0205(11) O2 0.0501(12) 0.0404(10) 0.0959(18) 0.000 0.000 -0.0020(8) O3 0.0635(13) 0.0434(11) 0.129(2) 0.000 0.000 -0.0107(10) N1 0.0425(11) 0.0371(11) 0.0492(13) 0.000 0.000 0.0003(9) N2 0.0447(11) 0.0436(12) 0.0469(13) 0.000 0.000 -0.0063(9) N3 0.102(2) 0.0441(14) 0.127(3) 0.000 0.000 -0.0179(15) C1 0.0480(16) 0.0551(17) 0.087(2) 0.000 0.000 -0.0103(13) C2 0.0460(14) 0.0454(14) 0.0533(16) 0.000 0.000 -0.0061(11) C3 0.050(2) 0.058(2) 0.187(6) 0.000 0.000 -0.0051(16) C4 0.0506(15) 0.0415(14) 0.0581(17) 0.000 0.000 -0.0085(11) C5 0.083(3) 0.0394(18) 0.139(4) 0.000 0.000 -0.0037(16) C6 0.0398(12) 0.0368(13) 0.0412(13) 0.000 0.000 -0.0044(9) C7 0.0331(12) 0.0460(14) 0.0484(14) 0.000 0.000 -0.0013(10) C8 0.0415(13) 0.0424(14) 0.0537(16) 0.000 0.000 0.0057(11) C9 0.0488(14) 0.0357(12) 0.0516(15) 0.000 0.000 -0.0021(10) C10 0.0383(13) 0.0446(14) 0.0704(19) 0.000 0.000 -0.0059(10) C11 0.0381(12) 0.0402(13) 0.0623(17) 0.000 0.000 0.0029(10) C12 0.0577(17) 0.0441(16) 0.079(2) 0.000 0.000 -0.0083(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 C1 1.204(4) . ? O2 C4 1.211(4) . ? O3 C4 1.322(3) . ? O3 C5 1.434(5) . ? N1 N2 1.309(3) . ? N1 C6 1.401(3) . ? N1 H1 0.86(3) . ? N2 C2 1.300(3) . ? N3 C12 1.142(4) . ? C1 C3 1.487(5) . ? C1 C2 1.489(4) . ? C2 C4 1.474(4) . ? C3 H31 0.88(4) . ? C3 H32 0.95(5) . ? C5 H51 1.02(4) . ? C5 H52 0.89(5) . ? C6 C11 1.387(3) . ? C6 C7 1.385(3) . ? C7 C8 1.359(4) . ? C7 H7 0.89(3) . ? C8 C9 1.390(4) . ? C8 H8 0.98(3) . ? C9 C10 1.393(4) . ? C9 C12 1.433(4) . ? C10 C11 1.382(4) . ? C10 H10 0.97(3) . ? C11 H11 1.04(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 C4 O3 C5 116.6(3) . . ? N2 N1 C6 119.3(2) . . ? N2 N1 H1 114(2) . . ? C6 N1 H1 127(2) . . ? C2 N2 N1 123.6(2) . . ? O1 C1 C3 120.0(3) . . ? O1 C1 C2 122.1(3) . . ? C3 C1 C2 117.9(3) . . ? N2 C2 C4 122.1(3) . . ? N2 C2 C1 113.6(3) . . ? C4 C2 C1 124.3(3) . . ? C1 C3 H31 106(3) . . ? C1 C3 H32 117(3) . . ? H31 C3 H32 109(3) . . ? O2 C4 O3 121.9(3) . . ? O2 C4 C2 122.8(3) . . ? O3 C4 C2 115.2(3) . . ? O3 C5 H51 106(2) . . ? O3 C5 H52 103(3) . . ? H51 C5 H52 114(2) . . ? C11 C6 C7 120.2(2) . . ? C11 C6 N1 117.9(2) . . ? C7 C6 N1 121.9(2) . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 119.9(17) . . ? C6 C7 H7 120.2(17) . . ? C7 C8 C9 121.1(2) . . ? C7 C8 H8 115.1(18) . . ? C9 C8 H8 123.8(18) . . ? C10 C9 C8 119.0(2) . . ? C10 C9 C12 120.8(2) . . ? C8 C9 C12 120.1(2) . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 113(2) . . ? C9 C10 H10 127(2) . . ? C10 C11 C6 119.7(2) . . ? C10 C11 H11 121.8(16) . . ? C6 C11 H11 118.6(16) . . ? N3 C12 C9 178.3(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.241 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.050 data_(6) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,4-pentanetrione-3-(2-carboxyphenylhydrazone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N4 O8' _chemical_formula_sum 'C24 H24 N4 O8' _chemical_formula_weight 496.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting ' monoclinic' _symmetry_space_group_name_H-M ' P 21/n ' 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 11.411(2) _cell_length_b 13.828(3) _cell_length_c 15.143(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.450(10) _cell_angle_gamma 90.00 _cell_volume 2363.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description ' plate' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.107 _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5325 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.96 _reflns_number_total 5125 _reflns_number_gt 2517 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; PARST (Nardelli, 1983, 1995), 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^)+(0.0657P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5125 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1289 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 O11 O -0.03416(15) 0.31738(15) -0.14246(11) 0.0753(6) Uani 1 1 d . . . O21 O 0.16614(14) 0.32529(15) -0.35044(13) 0.0794(6) Uani 1 1 d . . . O31 O -0.29832(14) 0.34570(14) -0.11893(10) 0.0665(5) Uani 1 1 d . . . O41 O -0.49255(14) 0.36067(15) -0.12453(11) 0.0695(6) Uani 1 1 d . . . N11 N -0.20979(16) 0.32903(14) -0.27120(13) 0.0472(5) Uani 1 1 d . . . N21 N -0.12740(15) 0.33223(13) -0.32364(12) 0.0465(5) Uani 1 1 d . . . C11 C -0.01428(19) 0.33204(16) -0.29227(15) 0.0454(5) Uani 1 1 d . . . C21 C 0.0343(2) 0.32682(17) -0.19685(16) 0.0519(6) Uani 1 1 d . . . C31 C 0.0601(2) 0.33611(19) -0.36505(16) 0.0567(6) Uani 1 1 d . . . C41 C 0.1644(3) 0.3347(3) -0.1642(2) 0.0730(9) Uani 1 1 d . . . C51 C -0.0006(3) 0.3523(4) -0.4578(2) 0.0869(12) Uani 1 1 d . . . C61 C -0.32828(18) 0.32602(16) -0.31122(14) 0.0432(5) Uani 1 1 d . . . C71 C -0.3566(2) 0.3153(2) -0.40329(16) 0.0558(7) Uani 1 1 d . . . C81 C -0.4724(2) 0.3114(2) -0.44261(17) 0.0637(8) Uani 1 1 d . . . C91 C -0.5634(2) 0.3184(2) -0.39296(18) 0.0621(7) Uani 1 1 d . . . C101 C -0.5373(2) 0.32884(19) -0.30218(17) 0.0547(7) Uani 1 1 d . . . C111 C -0.42036(19) 0.33364(16) -0.25927(14) 0.0442(5) Uani 1 1 d . . . C121 C -0.39825(19) 0.34620(18) -0.16250(15) 0.0484(6) Uani 1 1 d . . . O12 O -0.69552(15) 0.40885(16) 0.06814(12) 0.0779(6) Uani 1 1 d . . . O22 O -0.90348(16) 0.42637(19) 0.27060(16) 0.1080(8) Uani 1 1 d . . . O32 O -0.43495(13) 0.38925(14) 0.04897(10) 0.0645(5) Uani 1 1 d . . . O42 O -0.24014(14) 0.38323(15) 0.05438(11) 0.0680(6) Uani 1 1 d . . . N12 N -0.52379(15) 0.41597(14) 0.19976(13) 0.0452(5) Uani 1 1 d . . . N22 N -0.60652(15) 0.41951(13) 0.25113(12) 0.0466(5) Uani 1 1 d . . . C12 C -0.71995(19) 0.42194(17) 0.21697(16) 0.0492(6) Uani 1 1 d . . . C22 C -0.7650(2) 0.42242(19) 0.12096(17) 0.0583(7) Uani 1 1 d . . . C32 C -0.7973(2) 0.4223(2) 0.28847(19) 0.0635(7) Uani 1 1 d . . . C42 C -0.8922(3) 0.4421(3) 0.0855(3) 0.0841(11) Uani 1 1 d . . . C52 C -0.7404(3) 0.4178(4) 0.3830(2) 0.0856(11) Uani 1 1 d . . . C62 C -0.40489(17) 0.41804(16) 0.24031(14) 0.0426(5) Uani 1 1 d . . . C72 C -0.3775(2) 0.4317(2) 0.33196(16) 0.0554(7) Uani 1 1 d . . . C82 C -0.2623(2) 0.4320(2) 0.37236(17) 0.0635(7) Uani 1 1 d . . . C92 C -0.1713(2) 0.4188(2) 0.32319(18) 0.0617(7) Uani 1 1 d . . . C102 C -0.19656(19) 0.40698(19) 0.23294(16) 0.0533(6) Uani 1 1 d . . . C112 C -0.31330(18) 0.40649(17) 0.18896(14) 0.0440(5) Uani 1 1 d . . . C122 C -0.33564(19) 0.39276(18) 0.09218(15) 0.0501(6) Uani 1 1 d . . . H11 H -0.191(2) 0.3287(18) -0.2124(18) 0.070(8) Uiso 1 1 d . . . H41 H -0.464(3) 0.373(2) -0.059(2) 0.105(11) Uiso 1 1 d . . . H71 H -0.2935(19) 0.3106(15) -0.4363(14) 0.050(6) Uiso 1 1 d . . . H81 H -0.486(2) 0.3014(17) -0.5061(17) 0.063(7) Uiso 1 1 d . . . H91 H -0.643(2) 0.3131(18) -0.4181(17) 0.073(8) Uiso 1 1 d . . . H101 H -0.596(2) 0.3330(16) -0.2669(15) 0.055(7) Uiso 1 1 d . . . H411 H 0.176(3) 0.336(2) -0.097(2) 0.105(11) Uiso 1 1 d . . . H421 H 0.201(2) 0.384(2) -0.1871(18) 0.070(9) Uiso 1 1 d . . . H431 H 0.211(3) 0.281(2) -0.191(2) 0.104(11) Uiso 1 1 d . . . H511 H 0.048(3) 0.355(2) -0.496(2) 0.092(10) Uiso 1 1 d . . . H521 H -0.060(3) 0.302(2) -0.473(2) 0.106(13) Uiso 1 1 d . . . H531 H -0.044(4) 0.413(3) -0.455(3) 0.168(19) Uiso 1 1 d . . . H12 H -0.5402(19) 0.4082(16) 0.1392(16) 0.053(7) Uiso 1 1 d . . . H42 H -0.262(2) 0.368(2) -0.007(2) 0.088(9) Uiso 1 1 d . . . H72 H -0.438(2) 0.4410(16) 0.3615(14) 0.050(6) Uiso 1 1 d . . . H82 H -0.245(2) 0.4447(16) 0.4377(17) 0.063(7) Uiso 1 1 d . . . H92 H -0.092(2) 0.4168(19) 0.3494(17) 0.081(9) Uiso 1 1 d . . . H102 H -0.1393(19) 0.3982(15) 0.1973(14) 0.045(6) Uiso 1 1 d . . . H412 H -0.901(3) 0.443(3) 0.021(3) 0.150(17) Uiso 1 1 d . . . H422 H -0.915(2) 0.503(2) 0.1096(19) 0.086(10) Uiso 1 1 d . . . H432 H -0.944(4) 0.398(3) 0.117(3) 0.162(19) Uiso 1 1 d . . . H512 H -0.681(3) 0.462(3) 0.399(2) 0.116(14) Uiso 1 1 d . . . H522 H -0.696(4) 0.358(3) 0.398(3) 0.146(18) Uiso 1 1 d . . . H532 H -0.802(3) 0.426(2) 0.418(2) 0.114(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 O11 0.0598(11) 0.1170(18) 0.0493(10) 0.0071(10) 0.0089(9) 0.0091(11) O21 0.0413(10) 0.1158(18) 0.0842(14) -0.0017(12) 0.0193(9) 0.0073(10) O31 0.0474(10) 0.1125(16) 0.0420(9) -0.0031(9) 0.0142(7) 0.0050(10) O41 0.0461(10) 0.1187(17) 0.0464(10) -0.0010(10) 0.0159(8) 0.0090(10) N11 0.0402(10) 0.0639(14) 0.0394(11) -0.0020(10) 0.0120(8) -0.0016(9) N21 0.0421(10) 0.0523(13) 0.0477(10) 0.0011(9) 0.0159(8) 0.0028(9) C11 0.0404(12) 0.0479(14) 0.0490(13) 0.0024(10) 0.0107(10) 0.0047(10) C21 0.0516(14) 0.0525(16) 0.0517(14) 0.0000(12) 0.0080(11) 0.0056(12) C31 0.0441(13) 0.0663(17) 0.0627(16) 0.0022(13) 0.0178(11) 0.0068(12) C41 0.0549(17) 0.090(3) 0.072(2) -0.0045(19) 0.0004(15) -0.0058(18) C51 0.0623(19) 0.149(4) 0.0559(17) 0.021(2) 0.0309(15) 0.017(2) C61 0.0403(11) 0.0471(14) 0.0436(12) 0.0004(10) 0.0111(9) -0.0010(10) C71 0.0467(13) 0.0756(19) 0.0474(14) -0.0085(12) 0.0148(11) -0.0042(12) C81 0.0531(15) 0.092(2) 0.0448(15) -0.0100(14) 0.0046(11) -0.0036(14) C91 0.0397(14) 0.087(2) 0.0588(16) -0.0067(14) 0.0035(12) -0.0039(13) C101 0.0435(13) 0.0664(18) 0.0576(16) -0.0008(13) 0.0190(12) -0.0024(12) C111 0.0427(12) 0.0472(14) 0.0446(12) 0.0010(11) 0.0126(10) -0.0026(10) C121 0.0428(13) 0.0602(16) 0.0450(13) 0.0042(11) 0.0158(10) 0.0035(11) O12 0.0502(10) 0.1234(18) 0.0586(11) -0.0052(11) 0.0035(9) 0.0108(10) O22 0.0402(11) 0.166(2) 0.1237(18) -0.0266(16) 0.0315(11) -0.0094(12) O32 0.0432(9) 0.1088(16) 0.0423(9) 0.0000(9) 0.0092(7) 0.0115(9) O42 0.0431(9) 0.1193(17) 0.0449(10) 0.0072(11) 0.0173(8) 0.0100(10) N12 0.0340(10) 0.0611(14) 0.0416(11) -0.0014(9) 0.0097(8) 0.0043(9) N22 0.0390(10) 0.0518(13) 0.0520(11) -0.0020(9) 0.0163(8) 0.0013(9) C12 0.0360(12) 0.0487(15) 0.0641(15) -0.0063(12) 0.0118(10) -0.0003(10) C22 0.0433(13) 0.0600(17) 0.0698(18) -0.0074(13) 0.0019(12) 0.0027(12) C32 0.0452(15) 0.0668(19) 0.084(2) -0.0110(14) 0.0271(13) -0.0061(13) C42 0.0495(17) 0.099(3) 0.099(3) -0.023(2) -0.0069(17) 0.0215(18) C52 0.067(2) 0.123(3) 0.075(2) -0.007(2) 0.0371(18) -0.011(2) C62 0.0363(11) 0.0455(14) 0.0459(13) 0.0021(10) 0.0061(9) 0.0039(10) C72 0.0416(13) 0.0764(19) 0.0499(15) -0.0049(13) 0.0124(11) 0.0026(13) C82 0.0525(15) 0.090(2) 0.0464(15) -0.0106(14) 0.0021(12) -0.0027(14) C92 0.0380(13) 0.088(2) 0.0563(16) 0.0017(14) -0.0021(11) -0.0026(13) C102 0.0360(13) 0.0721(19) 0.0527(15) 0.0031(13) 0.0095(11) 0.0030(12) C112 0.0365(11) 0.0516(15) 0.0449(12) 0.0028(10) 0.0091(9) 0.0034(10) C122 0.0413(13) 0.0652(17) 0.0459(13) 0.0088(12) 0.0134(10) 0.0070(11) _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 O11 C21 1.223(3) . ? O21 C31 1.207(3) . ? O31 C121 1.231(2) . ? O41 C121 1.308(3) . ? O41 H41 1.02(3) . ? N11 N21 1.318(2) . ? N11 C61 1.399(3) . ? N11 H11 0.88(3) . ? N21 C11 1.308(3) . ? C11 C21 1.471(3) . ? C11 C31 1.488(3) . ? C21 C41 1.498(4) . ? C31 C51 1.489(4) . ? C41 H411 1.01(3) . ? C41 H421 0.90(3) . ? C41 H431 1.04(3) . ? C51 H511 0.86(3) . ? C51 H521 0.98(3) . ? C51 H531 0.98(4) . ? C61 C71 1.392(3) . ? C61 C111 1.406(3) . ? C71 C81 1.368(3) . ? C71 H71 0.94(2) . ? C81 C91 1.372(3) . ? C81 H81 0.96(2) . ? C91 C101 1.371(4) . ? C91 H91 0.94(2) . ? C101 C111 1.398(3) . ? C101 H101 0.92(2) . ? C111 C121 1.460(3) . ? O12 C22 1.221(3) . ? O22 C32 1.203(3) . ? O32 C122 1.223(3) . ? O42 C122 1.310(2) . ? O42 H42 0.95(3) . ? N12 N22 1.309(2) . ? N12 C62 1.405(3) . ? N12 H12 0.92(2) . ? N22 C12 1.322(3) . ? C12 C22 1.469(3) . ? C12 C32 1.494(3) . ? C22 C42 1.497(4) . ? C32 C52 1.484(5) . ? C42 H412 0.96(4) . ? C42 H422 0.97(3) . ? C42 H432 1.01(4) . ? C52 H512 0.91(4) . ? C52 H522 0.98(4) . ? C52 H532 0.95(3) . ? C62 C72 1.390(3) . ? C62 C112 1.401(3) . ? C72 C82 1.366(3) . ? C72 H72 0.88(2) . ? C82 C92 1.377(3) . ? C82 H82 1.00(2) . ? C92 C102 1.365(3) . ? C92 H92 0.93(3) . ? C102 C112 1.399(3) . ? C102 H102 0.91(2) . ? C112 C122 1.463(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 C121 O41 H41 107.2(17) . . ? N21 N11 C61 118.03(19) . . ? N21 N11 H11 121.1(16) . . ? C61 N11 H11 120.9(16) . . ? C11 N21 N11 122.30(19) . . ? N21 C11 C21 124.5(2) . . ? N21 C11 C31 111.8(2) . . ? C21 C11 C31 123.8(2) . . ? O11 C21 C11 118.8(2) . . ? O11 C21 C41 119.1(2) . . ? C11 C21 C41 122.2(2) . . ? O21 C31 C11 121.7(2) . . ? O21 C31 C51 120.4(2) . . ? C11 C31 C51 117.9(2) . . ? C21 C41 H411 108.3(17) . . ? C21 C41 H421 114.9(18) . . ? H411 C41 H421 112(2) . . ? C21 C41 H431 111.1(17) . . ? H411 C41 H431 114(2) . . ? H421 C41 H431 96(2) . . ? C31 C51 H511 112(2) . . ? C31 C51 H521 109(2) . . ? H511 C51 H521 112(3) . . ? C31 C51 H531 105(3) . . ? H511 C51 H531 112(3) . . ? H521 C51 H531 106(3) . . ? C71 C61 N11 120.31(19) . . ? C71 C61 C111 119.0(2) . . ? N11 C61 C111 120.64(19) . . ? C81 C71 C61 120.5(2) . . ? C81 C71 H71 122.3(13) . . ? C61 C71 H71 117.2(13) . . ? C71 C81 C91 121.3(2) . . ? C71 C81 H81 116.1(14) . . ? C91 C81 H81 122.6(14) . . ? C101 C91 C81 119.1(2) . . ? C101 C91 H91 118.1(16) . . ? C81 C91 H91 122.7(16) . . ? C91 C101 C111 121.5(2) . . ? C91 C101 H101 121.3(14) . . ? C111 C101 H101 117.2(14) . . ? C101 C111 C61 118.5(2) . . ? C101 C111 C121 119.0(2) . . ? C61 C111 C121 122.5(2) . . ? O31 C121 O41 121.5(2) . . ? O31 C121 C111 123.17(19) . . ? O41 C121 C111 115.3(2) . . ? C122 O42 H42 109.3(17) . . ? N22 N12 C62 118.29(18) . . ? N22 N12 H12 122.7(14) . . ? C62 N12 H12 118.8(14) . . ? N12 N22 C12 121.23(19) . . ? N22 C12 C22 124.6(2) . . ? N22 C12 C32 111.4(2) . . ? C22 C12 C32 124.0(2) . . ? O12 C22 C12 118.8(2) . . ? O12 C22 C42 118.8(3) . . ? C12 C22 C42 122.4(3) . . ? O22 C32 C52 120.2(3) . . ? O22 C32 C12 121.3(3) . . ? C52 C32 C12 118.5(2) . . ? C22 C42 H412 109(2) . . ? C22 C42 H422 109.0(17) . . ? H412 C42 H422 112(3) . . ? C22 C42 H432 109(3) . . ? H412 C42 H432 120(3) . . ? H422 C42 H432 98(3) . . ? C32 C52 H512 116(2) . . ? C32 C52 H522 113(3) . . ? H512 C52 H522 99(3) . . ? C32 C52 H532 106(2) . . ? H512 C52 H532 110(3) . . ? H522 C52 H532 112(3) . . ? C72 C62 C112 119.6(2) . . ? C72 C62 N12 120.00(19) . . ? C112 C62 N12 120.44(19) . . ? C82 C72 C62 120.5(2) . . ? C82 C72 H72 122.8(14) . . ? C62 C72 H72 116.6(14) . . ? C72 C82 C92 120.7(3) . . ? C72 C82 H82 118.7(13) . . ? C92 C82 H82 120.6(13) . . ? C102 C92 C82 119.5(2) . . ? C102 C92 H92 118.2(16) . . ? C82 C92 H92 122.3(16) . . ? C92 C102 C112 121.6(2) . . ? C92 C102 H102 122.9(13) . . ? C112 C102 H102 115.5(13) . . ? C102 C112 C62 118.1(2) . . ? C102 C112 C122 119.42(19) . . ? C62 C112 C122 122.46(19) . . ? O32 C122 O42 121.8(2) . . ? O32 C122 C112 123.53(19) . . ? O42 C122 C112 114.66(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.166 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.036