# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/269 data_global # SUPPLEMENTARY CRYSTALLOGRAPHIC DATA OF THE MANUSCRIPT: # On the Isomerism/Tautomerism of Hydrazones. # Crystal Structures, Study in Solution and Theoretical Calculations # of New Series of a-N-Heterocyclic Hydrazones _audit_creation_date 'May 23, 2000' _audit_creation_method 'PARSTCIF' # SUBMISSION DETAILS _publ_contact_author_name 'Gianluca Giorgi, Ph. D.' _publ_contact_author_address ; Centro Interdipartimentale di Analisi e Determinazioni Strutturali, Universit\`a degli Studi di Siena Via Aldo Moro I-53100 Siena Italy ; _publ_contact_author_email 'gianluca.giorgi@unisi.it' _publ_contact_author_fax '+39 0577 234135' _publ_contact_author_phone '+39 0577 234137' _publ_contact_letter ? _publ_requested_journal 'Journal of the Chemical Society, Perkin Transactions 2' #-------------------------- data section of block --------------------------- data_(5) #Quinoline derivative # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_type_symbol _atom_type_number_in_cell _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source # # symbol number description f' f'' source # 'O ' 8 'Oxygen ' 0.0106 0.0060 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'N ' 12 'Nitrogen ' 0.0061 0.0033 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'C ' 60 'Carbon ' 0.0033 0.0016 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'H ' 68 'Hydrogen ' 0.0000 0.0000 'Int. Tab. C, 4.2.6.8, 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_group # # Table of coordinates # -------------------- # #label x/a y/b z/c Ueq tmf typ calc sof dis O13 -0.0106(6) 0.7775(3) 0.0657(2) 0.0741(15) Uani O . . . O16 -0.0196(6) 0.9026(3) 0.1683(2) 0.0651(14) Uani O . . . N1 0.2793(5) 0.2662(3) 0.1900(2) 0.0396(12) Uani N . . . N9 0.1811(5) 0.4754(3) 0.1799(2) 0.0471(14) Uani N . . . N10 0.1193(5) 0.5796(3) 0.1412(2) 0.0434(13) Uani N . . . C2 0.2269(6) 0.3579(4) 0.1435(2) 0.0376(15) Uani C . . . C3 0.2138(6) 0.3448(4) 0.0653(2) 0.0411(16) Uani C . . . C4 0.2604(6) 0.2299(4) 0.0328(2) 0.0428(16) Uani C . . . C4A 0.3223(6) 0.1253(4) 0.0800(3) 0.0429(18) Uani C . . . C5 0.3829(7) 0.0010(5) 0.0525(3) 0.0574(21) Uani C . . . C6 0.4478(7) -0.0896(5) 0.1002(3) 0.0686(23) Uani C . . . C7 0.4482(7) -0.0661(5) 0.1781(3) 0.0572(22) Uani C . . . C8 0.3896(7) 0.0488(4) 0.2088(3) 0.0463(18) Uani C . . . C8A 0.3305(6) 0.1486(4) 0.1590(3) 0.0405(16) Uani C . . . C11 0.0922(6) 0.6856(4) 0.1790(3) 0.0415(16) Uani C . . . C12 0.0155(7) 0.7996(5) 0.1381(3) 0.0478(17) Uani C . . . C14 -0.0867(8) 0.8860(5) 0.0237(3) 0.0928(28) Uani C . . . C15 0.1318(6) 0.7044(4) 0.2610(2) 0.0538(18) Uani C . . . C17 0.2442(8) 0.2102(5) -0.0510(2) 0.0691(22) Uani C . . . C18 0.3840(7) 0.0687(5) 0.2926(2) 0.0620(20) Uani C . . . HN9 0.18912(0) 0.48196(0) 0.22895(0) 0.0566(60) Uiso H . . . H3 0.15748(0) 0.42122(0) 0.03630(0) 0.0566(60) Uiso H . . . H5 0.36905(0) -0.02075(0) -0.00162(0) 0.0566(60) Uiso H . . . H6 0.48136(0) -0.17241(0) 0.08438(0) 0.0566(60) Uiso H . . . H7 0.49784(0) -0.13132(0) 0.21251(0) 0.0566(60) Uiso H . . . H14A -0.09712(0) 0.86156(0) -0.02825(0) 0.0800(0) Uiso H calc . . H14B -0.01533(0) 0.96269(0) 0.02793(0) 0.0800(0) Uiso H calc . . H14C -0.19774(0) 0.90523(0) 0.04380(0) 0.0800(0) Uiso H calc . . H15A 0.11145(0) 0.79473(0) 0.27470(0) 0.0800(0) Uiso H calc . . H15B 0.24935(0) 0.68281(0) 0.27014(0) 0.0800(0) Uiso H calc . . H15C 0.05982(0) 0.64781(0) 0.29048(0) 0.0800(0) Uiso H calc . . H17A 0.16423(0) 0.14044(0) -0.06094(0) 0.0800(0) Uiso H calc . . H17B 0.35360(0) 0.18718(0) -0.07161(0) 0.0800(0) Uiso H calc . . H17C 0.20439(0) 0.29031(0) -0.07392(0) 0.0800(0) Uiso H calc . . H18A 0.27427(0) 0.10293(0) 0.30668(0) 0.0800(0) Uiso H calc . . H18B 0.47145(0) 0.13001(0) 0.30712(0) 0.0800(0) Uiso H calc . . H18C 0.40280(0) -0.01425(0) 0.31735(0) 0.0800(0) Uiso H calc . . 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 #label U11 U22 U33 U23 U13 U12 O13 0.1224(35) 0.0481(20) 0.0518(20) -0.0002(17) -0.0241(26) 0.0291(26) O16 0.0998(31) 0.0368(18) 0.0588(22) -0.0009(17) 0.0069(25) 0.0171(22) N1 0.0520(26) 0.0276(19) 0.0393(19) -0.0003(17) 0.0035(22) -0.0010(20) N9 0.0707(32) 0.0329(20) 0.0377(22) 0.0035(18) -0.0018(24) 0.0054(23) N10 0.0495(24) 0.0359(21) 0.0449(23) 0.0055(19) 0.0086(23) 0.0082(21) C2 0.0385(29) 0.0302(25) 0.0441(26) -0.0017(23) -0.0004(25) -0.0041(25) C3 0.0377(29) 0.0488(28) 0.0367(25) 0.0068(24) -0.0039(25) 0.0016(26) C4 0.0385(30) 0.0481(28) 0.0417(26) -0.0008(24) 0.0044(27) -0.0021(27) C4A 0.0407(30) 0.0327(26) 0.0554(31) -0.0053(24) 0.0043(26) -0.0097(26) C5 0.0634(37) 0.0492(30) 0.0595(33) -0.0154(27) 0.0066(31) 0.0039(31) C6 0.0807(50) 0.0411(29) 0.0839(41) -0.0080(32) 0.0094(39) 0.0126(33) C7 0.0617(42) 0.0371(27) 0.0727(37) 0.0067(29) 0.0010(33) 0.0055(30) C8 0.0520(34) 0.0333(26) 0.0537(31) 0.0033(24) 0.0008(28) -0.0052(28) C8A 0.0331(30) 0.0342(26) 0.0543(29) -0.0016(23) 0.0047(25) -0.0044(25) C11 0.0468(32) 0.0335(26) 0.0441(27) 0.0012(22) 0.0030(26) 0.0049(24) C12 0.0542(34) 0.0415(29) 0.0476(29) 0.0017(24) -0.0031(32) 0.0064(29) C14 0.1352(64) 0.0591(36) 0.0841(42) 0.0071(32) -0.0349(44) 0.0455(41) C15 0.0651(36) 0.0435(28) 0.0527(29) -0.0093(25) 0.0014(30) 0.0034(30) C17 0.0825(46) 0.0820(37) 0.0428(29) -0.0045(28) 0.0089(34) 0.0017(41) C18 0.0761(40) 0.0460(29) 0.0640(34) 0.0088(28) 0.0046(33) 0.0175(34) # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O13 C12 1.324(6) . . no O13 C14 1.456(6) . . no O16 C12 1.205(6) . . no N1 C2 1.310(5) . . no N1 C8A 1.372(5) . . no N9 N10 1.351(5) . . no N9 C2 1.402(5) . . no N9 HN9 0.876(4) . . no N10 C11 1.284(6) . . no C2 C3 1.401(6) . . no C3 C4 1.350(6) . . no C3 H3 1.029(4) . . no C4 C4A 1.436(6) . . no C4 C17 1.509(6) . . no C4A C5 1.432(6) . . no C4A C8A 1.426(7) . . no C5 C6 1.350(7) . . no C5 H5 0.993(5) . . no C6 C7 1.406(8) . . no C6 H6 0.923(5) . . no C7 C8 1.365(7) . . no C7 H7 0.980(5) . . no C8 C8A 1.422(6) . . no C8 C18 1.503(6) . . no C11 C12 1.491(6) . . no C11 C15 1.503(6) . . no C14 H14A 0.960(5) . . no C14 H14B 0.960(5) . . no C14 H14C 0.960(6) . . no C15 H15A 0.960(5) . . no C15 H15B 0.960(5) . . no C15 H15C 0.960(5) . . no C17 H17A 0.960(6) . . no C17 H17B 0.960(6) . . no C17 H17C 0.960(5) . . no C18 H18A 0.960(5) . . no C18 H18B 0.960(5) . . no C18 H18C 0.960(5) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O13 C14 115.7(4) . . . no C2 N1 C8A 117.0(3) . . . no N10 N9 C2 121.3(3) . . . no N10 N9 HN9 118.3(4) . . . no C2 N9 HN9 120.4(4) . . . no N9 N10 C11 116.5(3) . . . no N1 C2 N9 113.0(3) . . . no N1 C2 C3 125.6(4) . . . no N9 C2 C3 121.4(4) . . . no C2 C3 C4 119.1(4) . . . no C2 C3 H3 117.2(4) . . . no C4 C3 H3 123.4(4) . . . no C3 C4 C4A 118.5(4) . . . no C3 C4 C17 121.0(4) . . . no C4A C4 C17 120.5(4) . . . no C4 C4A C5 124.1(4) . . . no C4 C4A C8A 118.0(4) . . . no C5 C4A C8A 117.8(4) . . . no C4A C5 C6 120.5(4) . . . no C4A C5 H5 119.3(5) . . . no C6 C5 H5 120.0(5) . . . no C5 C6 C7 120.4(5) . . . no C5 C6 H6 122.2(5) . . . no C7 C6 H6 117.0(5) . . . no C6 C7 C8 122.5(5) . . . no C6 C7 H7 120.1(5) . . . no C8 C7 H7 117.3(4) . . . no C7 C8 C8A 117.8(4) . . . no C7 C8 C18 121.3(4) . . . no C8A C8 C18 120.8(4) . . . no N1 C8A C4A 121.7(4) . . . no N1 C8A C8 117.5(4) . . . no C4A C8A C8 120.7(4) . . . no N10 C11 C12 117.3(4) . . . no N10 C11 C15 125.4(4) . . . no C12 C11 C15 117.2(4) . . . no O13 C12 O16 123.0(4) . . . no O13 C12 C11 113.9(4) . . . no O16 C12 C11 123.0(4) . . . no O13 C14 H14A 109.5(4) . . . no O13 C14 H14B 109.5(4) . . . no O13 C14 H14C 109.5(5) . . . no H14A C14 H14B 109.5(5) . . . no H14A C14 H14C 109.5(5) . . . no H14B C14 H14C 109.5(6) . . . no C11 C15 H15A 109.5(4) . . . no C11 C15 H15B 109.5(4) . . . no C11 C15 H15C 109.5(4) . . . no H15A C15 H15B 109.5(4) . . . no H15A C15 H15C 109.5(4) . . . no H15B C15 H15C 109.5(5) . . . no C4 C17 H17A 109.5(4) . . . no C4 C17 H17B 109.5(4) . . . no C4 C17 H17C 109.5(4) . . . no H17A C17 H17B 109.5(6) . . . no H17A C17 H17C 109.5(5) . . . no H17B C17 H17C 109.5(6) . . . no C8 C18 H18A 109.5(4) . . . no C8 C18 H18B 109.5(4) . . . no C8 C18 H18C 109.5(4) . . . no H18A C18 H18B 109.5(5) . . . no H18A C18 H18C 109.5(5) . . . no H18B C18 H18C 109.5(5) . . . no # CHEMICAL DATA 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 7.8280(10) _cell_length_b 10.1310(10) _cell_length_c 17.783(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1410.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 2 _cell_measurement_theta_max 35 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type 'none' _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 'Siemens P4' _diffrn_measurement_method 'omega scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_reflns_number 1976 _diffrn_reflns_av_R_equivalents 0.0124 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.177 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.038 _reflns_number_total 1810 _reflns_number_gt 1052 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0404P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 1810 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1181 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 #===END #-------------------------- data section of block --------------------------- data_(6) #Phthalazine derivative # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_type_symbol _atom_type_number_in_cell _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source # # symbol number description f' f'' source # 'O ' 8 'Oxygen ' 0.0106 0.0060 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'N ' 16 'Nitrogen ' 0.0061 0.0033 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'C ' 48 'Carbon ' 0.0033 0.0016 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'H ' 48 'Hydrogen ' 0.0000 0.0000 'Int. Tab. C, 4.2.6.8, 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_group # # Table of coordinates # -------------------- # #label x/a y/b z/c Ueq tmf typ calc sof dis O13 0.6421(3) 0.4397(2) 0.1798(3) 0.0628(12) Uani O . . . O16 0.4991(2) 0.3236(2) 0.2026(3) 0.0711(14) Uani O . . . N2 1.0806(3) 0.4230(2) -0.0542(4) 0.0553(14) Uani N . . . N3 0.9757(3) 0.3770(2) -0.0194(3) 0.0469(12) Uani N . . . N9 0.8532(2) 0.2394(2) 0.0211(3) 0.0416(12) Uani N . . . N10 0.7781(3) 0.3111(2) 0.0672(3) 0.0408(12) Uani N . . . C1 1.1651(3) 0.3678(3) -0.0935(5) 0.0541(17) Uani C . . . C4 0.9533(3) 0.2795(2) -0.0189(4) 0.0383(15) Uani C . . . C4A 1.0482(3) 0.2182(2) -0.0682(4) 0.0368(15) Uani C . . . C5 1.0342(4) 0.1176(2) -0.0789(4) 0.0491(18) Uani C . . . C6 1.1274(4) 0.0635(3) -0.1231(4) 0.0587(18) Uani C . . . C7 1.2356(4) 0.1082(3) -0.1565(5) 0.0575(19) Uani C . . . C8 1.2499(3) 0.2075(3) -0.1479(5) 0.0518(17) Uani C . . . C8A 1.1550(3) 0.2637(3) -0.1040(4) 0.0434(15) Uani C . . . C11 0.6832(3) 0.2765(2) 0.1166(4) 0.0401(14) Uani C . . . C12 0.5986(4) 0.3475(3) 0.1696(4) 0.0452(15) Uani C . . . C14 0.5604(4) 0.5096(3) 0.2307(5) 0.0731(21) Uani C . . . C15 0.6509(3) 0.1713(2) 0.1267(5) 0.0548(16) Uani C . . . H3 0.93059(0) 0.41984(0) 0.01602(0) 0.0564(40) Uiso H . . . H1 1.23632(0) 0.40346(0) -0.11994(0) 0.0564(40) Uiso H . . . H5 0.95779(0) 0.08394(0) -0.06208(0) 0.0564(40) Uiso H . . . H6 1.11748(0) -0.00681(0) -0.12769(0) 0.0564(40) Uiso H . . . H7 1.29739(0) 0.06779(0) -0.18814(0) 0.0564(40) Uiso H . . . H8 1.32093(0) 0.24159(0) -0.17415(0) 0.0564(40) Uiso H . . . H14A 0.60650(0) 0.57214(0) 0.23630(0) 0.0800(0) Uiso H calc . . H14B 0.54885(0) 0.48508(0) 0.32741(0) 0.0800(0) Uiso H calc . . H14C 0.45741(0) 0.50954(0) 0.16179(0) 0.0800(0) Uiso H calc . . H15A 0.55749(0) 0.16320(0) 0.07539(0) 0.0800(0) Uiso H calc . . H15B 0.64970(0) 0.15278(0) 0.23027(0) 0.0800(0) Uiso H calc . . H15C 0.70168(0) 0.12860(0) 0.08434(0) 0.0800(0) Uiso H calc . . 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 #label U11 U22 U33 U23 U13 U12 O13 0.0698(17) 0.0487(16) 0.0964(22) -0.0023(15) 0.0619(17) 0.0031(13) O16 0.0546(15) 0.0769(18) 0.1041(23) -0.0172(17) 0.0558(16) -0.0097(15) N2 0.0537(18) 0.0435(17) 0.0849(26) 0.0040(17) 0.0444(19) -0.0025(15) N3 0.0475(17) 0.0378(17) 0.0685(23) -0.0018(16) 0.0368(17) 0.0027(14) N9 0.0398(14) 0.0415(17) 0.0528(20) 0.0001(14) 0.0277(15) 0.0005(14) N10 0.0375(14) 0.0423(18) 0.0483(20) -0.0031(15) 0.0224(15) 0.0007(13) C1 0.0465(22) 0.0534(24) 0.0755(31) 0.0027(22) 0.0378(22) -0.0034(18) C4 0.0386(18) 0.0367(21) 0.0438(24) 0.0011(18) 0.0197(18) 0.0038(16) C4A 0.0330(17) 0.0430(21) 0.0360(22) 0.0028(18) 0.0142(16) 0.0036(16) C5 0.0509(21) 0.0399(21) 0.0652(27) -0.0023(21) 0.0315(21) -0.0027(17) C6 0.0628(24) 0.0441(22) 0.0809(32) -0.0029(23) 0.0399(24) 0.0112(19) C7 0.0533(24) 0.0632(26) 0.0657(30) -0.0034(24) 0.0332(22) 0.0133(20) C8 0.0446(22) 0.0580(26) 0.0643(30) -0.0004(22) 0.0333(21) 0.0041(18) C8A 0.0383(19) 0.0483(22) 0.0514(27) 0.0020(19) 0.0257(19) 0.0029(17) C11 0.0355(18) 0.0490(21) 0.0422(23) 0.0007(18) 0.0216(18) -0.0026(16) C12 0.0409(19) 0.0518(24) 0.0473(24) -0.0040(20) 0.0212(18) -0.0015(19) C14 0.0844(28) 0.0579(26) 0.1094(36) -0.0033(26) 0.0741(29) 0.0089(23) C15 0.0508(20) 0.0514(22) 0.0757(28) 0.0009(22) 0.0391(21) -0.0060(19) # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O13 C12 1.333(4) . . no O13 C14 1.448(5) . . no O16 C12 1.202(5) . . no N2 N3 1.373(5) . . no N2 C1 1.289(5) . . no N3 C4 1.357(4) . . no N3 H3 0.874(3) . . no N9 N10 1.398(4) . . no N9 C4 1.319(5) . . no N10 C11 1.291(5) . . no C1 C8A 1.432(5) . . no C1 H1 0.974(4) . . no C4 C4A 1.465(5) . . no C4A C5 1.387(5) . . no C4A C8A 1.391(5) . . no C5 C6 1.373(6) . . no C5 H5 0.965(4) . . no C6 C7 1.388(6) . . no C6 H6 0.969(4) . . no C7 C8 1.369(5) . . no C7 H7 0.956(4) . . no C8 C8A 1.400(5) . . no C8 H8 0.961(4) . . no C11 C12 1.488(5) . . no C11 C15 1.491(5) . . no C14 H14A 0.971(4) . . no C14 H14B 0.969(5) . . no C14 H14C 1.012(3) . . no C15 H15A 0.906(3) . . no C15 H15B 0.960(4) . . no C15 H15C 0.946(4) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O13 C14 115.7(3) . . . no N3 N2 C1 116.5(3) . . . no N2 N3 C4 126.9(3) . . . no N2 N3 H3 109.2(3) . . . no C4 N3 H3 123.4(3) . . . no N10 N9 C4 110.4(3) . . . no N9 N10 C11 113.7(3) . . . no N2 C1 C8A 124.3(3) . . . no N2 C1 H1 113.8(3) . . . no C8A C1 H1 121.8(3) . . . no N3 C4 N9 124.0(3) . . . no N3 C4 C4A 115.7(3) . . . no N9 C4 C4A 120.3(3) . . . no C4 C4A C5 121.8(3) . . . no C4 C4A C8A 118.1(3) . . . no C5 C4A C8A 120.0(3) . . . no C4A C5 C6 119.5(3) . . . no C4A C5 H5 122.4(3) . . . no C6 C5 H5 118.1(4) . . . no C5 C6 C7 120.8(4) . . . no C5 C6 H6 118.5(3) . . . no C7 C6 H6 120.7(4) . . . no C6 C7 C8 120.3(3) . . . no C6 C7 H7 118.0(4) . . . no C8 C7 H7 121.6(4) . . . no C7 C8 C8A 119.5(3) . . . no C7 C8 H8 123.0(4) . . . no C8A C8 H8 117.4(3) . . . no C1 C8A C4A 118.4(3) . . . no C1 C8A C8 121.7(3) . . . no C4A C8A C8 119.8(3) . . . no N10 C11 C12 117.4(3) . . . no N10 C11 C15 125.9(3) . . . no C12 C11 C15 116.6(3) . . . no O13 C12 O16 122.3(3) . . . no O13 C12 C11 115.1(3) . . . no O16 C12 C11 122.6(3) . . . no O13 C14 H14A 106.1(3) . . . no O13 C14 H14B 108.4(3) . . . no O13 C14 H14C 113.7(3) . . . no H14A C14 H14B 118.2(4) . . . no H14A C14 H14C 114.4(4) . . . no H14B C14 H14C 96.0(3) . . . no C11 C15 H15A 107.8(3) . . . no C11 C15 H15B 113.2(3) . . . no C11 C15 H15C 114.2(3) . . . no H15A C15 H15B 94.4(3) . . . no H15A C15 H15C 110.8(4) . . . no H15B C15 H15C 114.6(4) . . . no # CHEMICAL DATA 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 10.2350(10) _cell_length_b 13.717(2) _cell_length_c 8.8950(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.000(10) _cell_angle_gamma 90.00 _cell_volume 1165.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 45 _cell_measurement_theta_min 2 _cell_measurement_theta_max 34 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'none' _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 'Siemens P4' _diffrn_measurement_method 'omega scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_reflns_number 4349 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.1051 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2050 _reflns_number_gt 978 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0406P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2050 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1572 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.002 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.151 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.039