# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 1145/276 data_global _audit_creation_method SHELXL #------------------ SUBMISSION DETAILS --------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Gainsford, Graeme J.' _publ_contact_author_address ;Industrial Research Limited PO Box 31-310 Lower Hutt New Zealand ; _publ_contact_author_email g.gainsford@irl.cri.nz _publ_contact_author_fax '64(4)5690142' _publ_contact_author_phone '64(4)5690815' #--------_publ_requested_journal 'test' _publ_requested_journal 'J Mat. Chem.' _publ_contact_letter # Include date of submission ; Date of submission September-October , 2000 This CIF submission is supplementary data for a publication in J Materials Chemistry ; # _publ_requested_category 'FM' #------------------ TITLE AND AUTHOR LIST------------------------------------# _publ_section_title ; C~19~H~18~N~2~O~4~ ; loop_ _publ_author_name _publ_author_address 'Woolhouse, Antony D.' ;Industrial Research Limited PO Box 31-310 Lower Hutt New Zealand ; 'Gainsford, Graeme J.' ;Industrial Research Limited PO Box 31-310 Lower Hutt New Zealand ; #------------------ TEXT ----------------------------------------------------# _publ_section_synopsis ; The title compound C~19~H~18~N~2~O~4~ is presented. ; _publ_section_abstract ; The title compound C~19~H~18~N~2~O~4~ is presented. ; _publ_section_comment ; No comments ... see J Mat. Chem. ; _publ_section_exptl_prep ; See J Mat. Chem. ; _publ_section_exptl_refinement ; All hydrogens were constrained to an isotropic thermal parameter 1.2 times that of the equivalent U of their parent atom. ; # Insert blank lines between references _publ_section_references ; ConQuest Version 1.0, Cambridge Structural Database version 5.19 (April 2000), The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, U.K. CB2 1EZ. Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, p 565. Farrugia, L. J. (1999) WinGX - A Windows Program for Crystal Structure Analysis, J. Appl. Cryst. 32, 837-838. Johnson, C.K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. SAINT & SADABS software (1994-1996), Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. SMART software (1996), Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Spek, A.L., (1990). PLATON, Acta Cryst. A46, C34. ; _publ_section_figure_captions ; Fig 1. C~19~H~18~N~2~O~4~ [Johnson(1976), Farrugia(1997), Farrugia(1999), Spek(1990)] Displacement ellipsoids are drawn at the 30% probability level. ; _publ_section_acknowledgements ; We wish to thank Professor Ward T. Robinson, University of Canterbury, for collection of the diffraction data. ; data_w922 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H18 N2 O4' _chemical_formula_weight 338.35 _chemical_melting_point ? _chemical_compound_source ? 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 7.761(6) _cell_length_b 10.257(7) _cell_length_c 11.119(8) _cell_angle_alpha 73.408(12) _cell_angle_beta 80.744(12) _cell_angle_gamma 70.240(14) _cell_volume 796.3(10) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2500 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 24.2 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'CCD area detector' _diffrn_radiation_monochromator graphite _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 8.192 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4056 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.2525 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.08 _reflns_number_total 2902 _reflns_number_observed 896 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2902 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2327 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.1719 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_all 0.793 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 0.793 _refine_ls_restrained_S_obs 1.217 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.424 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.047 _atoms_sites_solution_primary 'direct methods' _atoms_sites_solution_secondary 'Fourier difference' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2085(7) 0.2363(5) 0.7902(4) 0.1035(17) Uani 1 d . . H1 H 0.2514 0.3034 0.7524 0.155 Uiso 1 calc R . O3 O 0.3454(6) 0.4612(4) -0.2735(4) 0.0706(14) Uani 1 d . . N1 N 0.3657(7) 0.3302(5) 0.3858(4) 0.0461(13) Uani 1 d . . N2 N 0.0242(6) 0.7906(5) -0.3779(4) 0.0550(14) Uani 1 d . . C1 C 0.2855(10) 0.1164(7) 0.7267(5) 0.091(2) Uani 1 d . . H1A H 0.2169 0.0461 0.7570 0.109 Uiso 1 calc R . H1B H 0.4165 0.0669 0.7424 0.109 Uiso 1 calc R . C3 C 0.3950(8) 0.2714(6) 0.5213(5) 0.0552(17) Uani 1 d . . H3A H 0.3773 0.3506 0.5609 0.066 Uiso 1 calc R . H3B H 0.5225 0.2072 0.5320 0.066 Uiso 1 calc R . C4 C 0.2380(8) 0.4548(6) 0.3437(5) 0.0558(17) Uani 1 d . . H4 H 0.1707 0.5088 0.4021 0.067 Uiso 1 calc R . C5 C 0.2007(7) 0.5069(6) 0.2217(5) 0.0499(16) Uani 1 d . . H5 H 0.1054 0.5942 0.1966 0.060 Uiso 1 calc R . C6 C 0.3015(7) 0.4333(6) 0.1318(5) 0.0411(15) Uani 1 d . . C7 C 0.4329(7) 0.3034(6) 0.1792(5) 0.0464(15) Uani 1 d . . H7 H 0.5028 0.2470 0.1231 0.056 Uiso 1 calc R . C8 C 0.4634(8) 0.2555(6) 0.3031(5) 0.0538(17) Uani 1 d . . H8 H 0.5557 0.1673 0.3317 0.065 Uiso 1 calc R . C9 C 0.2735(7) 0.4834(6) 0.0003(5) 0.0485(16) Uani 1 d . . H9 H 0.3415 0.4203 -0.0509 0.058 Uiso 1 calc R . C10 C 0.1627(7) 0.6085(6) -0.0581(5) 0.0500(16) Uani 1 d . . H10 H 0.0972 0.6726 -0.0074 0.060 Uiso 1 calc R . C11 C 0.1318(7) 0.6566(6) -0.1884(5) 0.0402(15) Uani 1 d . . C14 C 0.2266(9) 0.5758(7) -0.2776(5) 0.0573(18) Uani 1 d . . O13 O 0.1555(6) 0.6589(4) -0.3919(3) 0.0657(12) Uani 1 d . . C12 C 0.0149(8) 0.7865(6) -0.2576(5) 0.0484(16) Uani 1 d . . C15 C -0.1056(7) 0.9160(6) -0.2187(5) 0.0434(15) Uani 1 d . . C16 C -0.1378(8) 1.0456(6) -0.3038(5) 0.0517(16) Uani 1 d . . H16 H -0.0868 1.0509 -0.3880 0.062 Uiso 1 calc R . C17 C -0.2426(8) 1.1680(6) -0.2694(6) 0.0588(18) Uani 1 d . . H17 H -0.2637 1.2573 -0.3300 0.071 Uiso 1 calc R . C18 C -0.3170(8) 1.1635(7) -0.1494(6) 0.0667(19) Uani 1 d . . H18 H -0.3862 1.2491 -0.1251 0.080 Uiso 1 calc R . C19 C -0.2904(9) 1.0327(7) -0.0638(5) 0.069(2) Uani 1 d . . H19 H -0.3454 1.0281 0.0194 0.083 Uiso 1 calc R . C20 C -0.1848(8) 0.9080(6) -0.0970(5) 0.0617(18) Uani 1 d . . H20 H -0.1668 0.8181 -0.0374 0.074 Uiso 1 calc R . C2 C 0.2624(11) 0.1893(7) 0.5858(5) 0.0546(17) Uani 1 d . . H21_a H 0.1344 0.2561 0.5760 0.066 Uiso 1 calc R 1 O2A_a O 0.2808(7) 0.0728(5) 0.5351(5) 0.068(2) Uani 0.801(7) d P 1 H2A_a H 0.2238 0.1027 0.4695 0.102 Uiso 0.801(7) calc PR 1 O2B_b O 0.101(2) 0.270(2) 0.5684(14) 0.046(7) Uani 0.199(7) d P 2 H2B_b H 0.0568 0.2461 0.5172 0.068 Uiso 0.199(7) calc PR 2 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 0.104(4) 0.119(4) 0.074(3) -0.011(3) -0.005(3) -0.028(4) O3 0.077(3) 0.058(3) 0.066(3) -0.031(2) -0.008(2) 0.007(3) N1 0.053(3) 0.042(3) 0.038(3) -0.014(2) -0.005(2) -0.004(3) N2 0.060(3) 0.058(3) 0.041(3) -0.015(3) -0.009(3) -0.004(3) C1 0.098(6) 0.110(6) 0.057(4) -0.052(4) -0.033(4) 0.016(5) C3 0.060(4) 0.062(4) 0.037(3) -0.006(3) -0.013(3) -0.010(4) C4 0.067(5) 0.046(4) 0.049(4) -0.023(3) 0.004(4) -0.005(4) C5 0.043(4) 0.049(4) 0.047(4) -0.008(3) -0.009(3) -0.001(3) C6 0.038(4) 0.046(4) 0.037(3) -0.011(3) 0.003(3) -0.011(3) C7 0.048(4) 0.043(4) 0.044(4) -0.019(3) -0.008(3) -0.001(3) C8 0.046(4) 0.053(4) 0.054(4) -0.007(3) -0.017(3) -0.004(3) C9 0.045(4) 0.048(4) 0.047(4) -0.015(3) 0.000(3) -0.007(3) C10 0.044(4) 0.057(4) 0.048(4) -0.026(3) -0.004(3) -0.003(3) C11 0.043(4) 0.047(4) 0.034(3) -0.008(3) -0.004(3) -0.020(3) C14 0.065(5) 0.069(5) 0.046(4) -0.024(4) -0.012(4) -0.018(4) O13 0.082(3) 0.065(3) 0.045(2) -0.027(2) -0.003(2) -0.006(3) C12 0.047(4) 0.062(4) 0.036(3) -0.008(3) -0.010(3) -0.017(4) C15 0.043(4) 0.050(4) 0.034(3) -0.009(3) -0.007(3) -0.010(3) C16 0.066(4) 0.046(4) 0.039(3) -0.001(3) -0.004(3) -0.020(4) C17 0.059(5) 0.049(4) 0.068(5) -0.010(4) -0.019(4) -0.012(4) C18 0.064(5) 0.062(5) 0.058(4) -0.019(4) -0.006(4) 0.004(4) C19 0.072(5) 0.070(5) 0.043(4) -0.008(4) -0.004(3) 0.000(4) C20 0.056(4) 0.055(4) 0.046(4) -0.005(3) -0.007(3) 0.013(4) C2 0.082(6) 0.043(4) 0.041(4) -0.008(3) -0.016(4) -0.019(4) O2A_a 0.063(4) 0.076(4) 0.069(4) -0.030(3) -0.022(3) -0.010(3) O2B_b 0.025(12) 0.076(15) 0.028(10) -0.043(10) -0.007(9) 0.021(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 O1 C1 1.494(6) . Y O1 H1 0.8400 . N O3 C14 1.219(6) . Y N1 C8 1.340(6) . Y N1 C4 1.337(6) . Y N1 C3 1.478(6) . Y N2 C12 1.318(6) . Y N2 O13 1.423(5) . Y C1 C2 1.542(7) . Y C1 H1A 0.9900 . N C1 H1B 0.9900 . N C3 C2 1.512(7) . Y C3 H3A 0.9900 . N C3 H3B 0.9900 . N C4 C5 1.348(7) . Y C4 H4 0.9500 . N C5 C6 1.401(6) . Y C5 H5 0.9500 . N C6 C7 1.395(6) . Y C6 C9 1.431(7) . Y C7 C8 1.354(7) . Y C7 H7 0.9500 . N C8 H8 0.9500 . N C9 C10 1.328(6) . Y C9 H9 0.9500 . N C10 C11 1.423(7) . Y C10 H10 0.9500 . N C11 C12 1.418(6) . Y C11 C14 1.426(7) . Y C14 O13 1.391(6) . Y C12 C15 1.478(7) . Y C15 C16 1.364(6) . N C15 C20 1.384(7) . N C16 C17 1.366(7) . N C16 H16 0.9500 . N C17 C18 1.361(7) . N C17 H17 0.9500 . N C18 C19 1.376(7) . N C18 H18 0.9500 . N C19 C20 1.381(7) . N C19 H19 0.9500 . N C20 H20 0.9500 . N C2 O2B_b 1.253(15) . N C2 O2A_a 1.418(6) . N C2 H21_a 1.0000 . N O2A_a H2A_a 0.8400 . N O2B_b H2B_b 0.8400 . N loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5(4) . . N C8 N1 C4 118.7(5) . . Y C8 N1 C3 119.9(5) . . Y C4 N1 C3 121.4(5) . . N C12 N2 O13 105.5(4) . . Y O1 C1 C2 104.4(5) . . N O1 C1 H1A 110.9(4) . . N C2 C1 H1A 110.9(4) . . N O1 C1 H1B 110.9(3) . . N C2 C1 H1B 110.9(4) . . N H1A C1 H1B 108.9 . . N N1 C3 C2 110.7(4) . . N N1 C3 H3A 109.5(3) . . N C2 C3 H3A 109.5(3) . . N N1 C3 H3B 109.5(3) . . N C2 C3 H3B 109.5(4) . . N H3A C3 H3B 108.1 . . N N1 C4 C5 122.7(5) . . N N1 C4 H4 118.7(3) . . N C5 C4 H4 118.7(4) . . N C4 C5 C6 120.5(5) . . N C4 C5 H5 119.8(4) . . N C6 C5 H5 119.8(3) . . N C5 C6 C7 115.2(5) . . N C5 C6 C9 123.8(5) . . N C7 C6 C9 121.0(5) . . N C8 C7 C6 121.8(5) . . N C8 C7 H7 119.1(4) . . N C6 C7 H7 119.1(3) . . N N1 C8 C7 121.1(5) . . N N1 C8 H8 119.4(3) . . N C7 C8 H8 119.4(4) . . N C10 C9 C6 127.0(5) . . Y C10 C9 H9 116.5(3) . . N C6 C9 H9 116.5(3) . . N C9 C10 C11 126.9(5) . . Y C9 C10 H10 116.5(3) . . N C11 C10 H10 116.5(3) . . N C12 C11 C14 106.2(5) . . Y C12 C11 C10 130.6(5) . . Y C14 C11 C10 123.2(5) . . N O3 C14 O13 119.6(5) . . N O3 C14 C11 135.4(6) . . N O13 C14 C11 104.9(5) . . N C14 O13 N2 111.1(4) . . Y N2 C12 C11 112.2(5) . . N N2 C12 C15 116.5(5) . . N C11 C12 C15 131.2(5) . . N C16 C15 C20 119.5(5) . . N C16 C15 C12 119.3(5) . . N C20 C15 C12 121.1(5) . . N C17 C16 C15 120.8(5) . . N C17 C16 H16 119.6(4) . . N C15 C16 H16 119.6(3) . . N C16 C17 C18 120.8(6) . . N C16 C17 H17 119.6(4) . . N C18 C17 H17 119.6(4) . . N C17 C18 C19 118.8(6) . . N C17 C18 H18 120.6(4) . . N C19 C18 H18 120.6(4) . . N C20 C19 C18 121.0(6) . . N C20 C19 H19 119.5(3) . . N C18 C19 H19 119.5(4) . . N C19 C20 C15 119.0(5) . . N C19 C20 H20 120.5(3) . . N C15 C20 H20 120.5(4) . . N O2B_b C2 C3 109.1(11) . . N O2A_a C2 C3 112.8(6) . . N O2B_b C2 C1 110.9(10) . . N O2A_a C2 C1 102.3(5) . . N C3 C2 C1 115.6(5) . . N O2A_a C2 H21_a 108.6(4) . . N C3 C2 H21_a 108.6(4) . . N C1 C2 H21_a 108.6(4) . . N C2 O2A_a H2A_a 109.5(3) . . N C2 O2B_b H2B_b 109.5(8) . . N loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C3 C2 -92.8(6) . . . . N C4 N1 C3 C2 84.5(7) . . . . N C8 N1 C4 C5 1.4(9) . . . . N C3 N1 C4 C5 -175.9(6) . . . . N N1 C4 C5 C6 -2.4(9) . . . . N C4 C5 C6 C7 2.6(8) . . . . N C4 C5 C6 C9 -178.3(6) . . . . N C5 C6 C7 C8 -2.1(8) . . . . N C9 C6 C7 C8 178.9(6) . . . . N C4 N1 C8 C7 -0.8(8) . . . . N C3 N1 C8 C7 176.6(5) . . . . N C6 C7 C8 N1 1.2(9) . . . . N C5 C6 C9 C10 5.9(9) . . . . Y C7 C6 C9 C10 -175.1(6) . . . . N C6 C9 C10 C11 -178.4(5) . . . . Y C9 C10 C11 C12 178.9(6) . . . . Y C9 C10 C11 C14 -3.2(9) . . . . Y C12 C11 C14 O3 177.1(7) . . . . N C10 C11 C14 O3 -1.2(11) . . . . N C12 C11 C14 O13 -2.4(6) . . . . N C10 C11 C14 O13 179.3(5) . . . . N O3 C14 O13 N2 -177.7(5) . . . . N C11 C14 O13 N2 1.9(6) . . . . N C12 N2 O13 C14 -0.6(6) . . . . N O13 N2 C12 C11 -1.0(6) . . . . N O13 N2 C12 C15 176.5(4) . . . . N C14 C11 C12 N2 2.2(6) . . . . N C10 C11 C12 N2 -179.7(5) . . . . N C14 C11 C12 C15 -174.9(6) . . . . N C10 C11 C12 C15 3.3(10) . . . . N N2 C12 C15 C16 -27.0(8) . . . . N C11 C12 C15 C16 150.0(6) . . . . N N2 C12 C15 C20 153.6(5) . . . . N C11 C12 C15 C20 -29.4(9) . . . . N C20 C15 C16 C17 2.0(8) . . . . N C12 C15 C16 C17 -177.4(5) . . . . N C15 C16 C17 C18 0.1(9) . . . . N C16 C17 C18 C19 -2.2(9) . . . . N C17 C18 C19 C20 2.2(10) . . . . N C18 C19 C20 C15 -0.1(9) . . . . N C16 C15 C20 C19 -2.0(8) . . . . N C12 C15 C20 C19 177.4(6) . . . . N N1 C3 C2 O2B_b -57.0(10) . . . . N N1 C3 C2 O2A_a 59.8(7) . . . . N N1 C3 C2 C1 177.2(5) . . . . N O1 C1 C2 O2B_b -50.2(12) . . . . N O1 C1 C2 O2A_a -162.2(5) . . . . N O1 C1 C2 C3 74.7(8) . . . . N