# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/287 data_20 _publ_requested_journal 'J. Chem. Soc., Perkin 1' _audit_creation_method 'manual edited SHELXL-97 .cif file' _chemical_name_systematic ; 4-Ethyl 14-Methyl 3-Methyl-15-oxo-17-oxa-2,16-diazapentacyclo[12.2.1.0^1,12^. 0^5,16^.0^6,11^]heptadeca-6,8,10-triene-4,14-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 N2 O6' _chemical_formula_sum 'C20 H22 N2 O6' _chemical_formula_weight 386.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 14.998(3) _cell_length_b 9.397(2) _cell_length_c 14.153(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.847(18) _cell_angle_gamma 90.00 _cell_volume 1851.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 71 _cell_measurement_theta_min 12.57 _cell_measurement_theta_max 14.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe 4-circle' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 5051 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4024 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'local program' _computing_cell_refinement 'local program' _computing_data_reduction 'local program' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1965)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The H-atoms of the tertiary C-H groups were refined with all X-C-H angles equal at a C-H distance of 0.98 \%A (AFIX 13 of SHELXL97). The H-atoms of the CH~2~ groups were refined with common isotropic displacement parameters for the H-atoms of the same group and idealized geometry with approximately tetrahedral angles and C-H distances of 0.97 \%A (AFIX 23 of SHELXL97). The H-atoms of the methyl groups were refined with common isotropic displacement parameters for the H-atoms of the same group and idealized geometry with tetrahedral angles, staggered conformation, and C-H distances of 0.96 \%A (AFIX 33 of SHELXL97). The C atoms of the phenyl ring were refined without any constraints. The H-atoms H7, H8, H9 and H10 were put at the external bisector of the C-C-C angle at a C-H distance of 0.93 \%A and refined with one common isotropic displacement parameter (AFIX 43 of SHELXL97). ; _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^)+(0.0434P)^2^+0.6168P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4024 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.79601(13) 0.8907(2) 0.40429(15) 0.0323(4) Uani 1 1 d . . . N2 N 0.73703(13) 0.9518(2) 0.30973(14) 0.0373(4) Uani 1 1 d . . . H2 H 0.7111(17) 1.025(3) 0.3205(18) 0.046(7) Uiso 1 1 d . . . C3 C 0.65818(14) 0.8527(2) 0.25288(15) 0.0368(5) Uani 1 1 d . . . H3 H 0.6886 0.7687 0.2369 0.033(5) Uiso 1 1 calc R . . C31 C 0.59660(17) 0.9191(3) 0.15160(17) 0.0509(6) Uani 1 1 d . . . H311 H 0.6369 0.9488 0.1161 0.067(5) Uiso 1 1 calc R . . H312 H 0.5631 1.0000 0.1635 0.067(5) Uiso 1 1 calc R . . H313 H 0.5509 0.8503 0.1113 0.067(5) Uiso 1 1 calc R . . C4 C 0.60043(13) 0.7995(2) 0.31704(15) 0.0339(5) Uani 1 1 d . . . H4 H 0.5592 0.7212 0.2796 0.032(5) Uiso 1 1 calc R . . C5 C 0.66948(13) 0.7393(2) 0.42178(15) 0.0315(4) Uani 1 1 d . . . H5 H 0.6331 0.7188 0.4652 0.025(5) Uiso 1 1 calc R . . C6 C 0.71999(13) 0.6050(2) 0.40794(15) 0.0328(4) Uani 1 1 d . . . C7 C 0.67920(15) 0.4710(2) 0.40705(17) 0.0408(5) Uani 1 1 d . . . H7 H 0.6219 0.4636 0.4178 0.051(3) Uiso 1 1 calc R . . C8 C 0.72307(17) 0.3495(2) 0.39039(19) 0.0494(6) Uani 1 1 d . . . H8 H 0.6959 0.2607 0.3910 0.051(3) Uiso 1 1 calc R . . C9 C 0.80783(17) 0.3605(2) 0.37276(19) 0.0498(6) Uani 1 1 d . . . H9 H 0.8372 0.2792 0.3604 0.051(3) Uiso 1 1 calc R . . C10 C 0.84841(15) 0.4926(2) 0.37360(18) 0.0442(6) Uani 1 1 d . . . H10 H 0.9050 0.4990 0.3613 0.051(3) Uiso 1 1 calc R . . C11 C 0.80662(13) 0.6167(2) 0.39251(15) 0.0334(5) Uani 1 1 d . . . C12 C 0.85827(13) 0.7589(2) 0.40280(16) 0.0334(5) Uani 1 1 d . . . H12 H 0.8845 0.7691 0.3493 0.038(6) Uiso 1 1 calc R . . C13 C 0.93991(14) 0.7753(2) 0.51044(16) 0.0376(5) Uani 1 1 d . . . H131 H 0.9478 0.6892 0.5504 0.047(4) Uiso 1 1 calc R . . H132 H 1.0007 0.8000 0.5052 0.047(4) Uiso 1 1 calc R . . C14 C 0.90061(14) 0.8991(2) 0.55599(16) 0.0364(5) Uani 1 1 d . . . C15 C 0.80847(14) 0.8396(2) 0.56701(16) 0.0342(5) Uani 1 1 d . . . O15 O 0.79880(11) 0.78915(18) 0.64146(11) 0.0489(4) Uani 1 1 d . . . N16 N 0.74153(11) 0.84929(17) 0.46930(12) 0.0310(4) Uani 1 1 d . . . O17 O 0.86172(10) 0.99181(14) 0.46875(11) 0.0383(4) Uani 1 1 d . . . C41 C 0.53588(14) 0.9119(2) 0.33621(15) 0.0360(5) Uani 1 1 d . . . O41 O 0.54573(11) 1.03919(17) 0.33433(13) 0.0515(4) Uani 1 1 d . . . O42 O 0.46558(10) 0.84863(16) 0.35718(13) 0.0482(4) Uani 1 1 d . . . C42 C 0.39367(15) 0.9382(3) 0.37487(19) 0.0492(6) Uani 1 1 d . . . H421 H 0.3556 0.9885 0.3132 0.061(5) Uiso 1 1 calc R . . H422 H 0.4243 1.0074 0.4279 0.061(5) Uiso 1 1 calc R . . C43 C 0.3320(2) 0.8398(3) 0.4067(2) 0.0737(9) Uani 1 1 d . . . H431 H 0.2831 0.8935 0.4193 0.103(7) Uiso 1 1 calc R . . H432 H 0.3707 0.7908 0.4677 0.103(7) Uiso 1 1 calc R . . H433 H 0.3024 0.7719 0.3535 0.103(7) Uiso 1 1 calc R . . C51 C 0.96851(15) 0.9749(2) 0.64929(17) 0.0420(5) Uani 1 1 d . . . O51 O 0.96446(13) 1.09961(19) 0.66477(15) 0.0689(6) Uani 1 1 d . . . O52 O 1.03077(12) 0.88330(18) 0.70990(12) 0.0560(5) Uani 1 1 d . . . C52 C 1.09738(18) 0.9367(3) 0.80742(19) 0.0612(7) Uani 1 1 d . . . H521 H 1.1387 0.8609 0.8440 0.148(10) Uiso 1 1 calc R . . H522 H 1.0618 0.9723 0.8465 0.148(10) Uiso 1 1 calc R . . H523 H 1.1354 1.0119 0.7959 0.148(10) Uiso 1 1 calc R . . 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 C1 0.0321(10) 0.0293(10) 0.0354(11) 0.0013(9) 0.0124(9) -0.0040(8) N2 0.0375(9) 0.0341(10) 0.0393(10) 0.0047(8) 0.0134(8) 0.0019(8) C3 0.0341(10) 0.0393(12) 0.0364(11) -0.0011(9) 0.0125(9) 0.0044(9) C31 0.0485(13) 0.0612(16) 0.0402(13) 0.0038(12) 0.0131(11) 0.0042(12) C4 0.0286(9) 0.0341(11) 0.0378(11) -0.0028(9) 0.0109(8) 0.0000(8) C5 0.0288(9) 0.0299(10) 0.0383(11) -0.0002(9) 0.0153(9) -0.0022(8) C6 0.0313(10) 0.0290(10) 0.0358(11) 0.0014(9) 0.0099(8) 0.0007(8) C7 0.0413(12) 0.0323(11) 0.0497(13) -0.0001(10) 0.0179(10) -0.0047(9) C8 0.0573(14) 0.0272(11) 0.0606(15) -0.0014(11) 0.0186(12) -0.0041(10) C9 0.0532(14) 0.0315(12) 0.0635(16) -0.0056(11) 0.0204(12) 0.0094(11) C10 0.0357(11) 0.0412(13) 0.0561(14) -0.0041(11) 0.0175(11) 0.0046(10) C11 0.0310(10) 0.0322(11) 0.0362(11) 0.0007(9) 0.0114(9) 0.0022(8) C12 0.0306(10) 0.0338(11) 0.0382(11) -0.0002(9) 0.0154(9) -0.0008(8) C13 0.0303(10) 0.0371(12) 0.0444(12) 0.0013(10) 0.0126(9) -0.0008(9) C14 0.0344(10) 0.0331(11) 0.0385(11) 0.0001(9) 0.0097(9) -0.0036(9) C15 0.0357(10) 0.0297(10) 0.0365(11) -0.0014(9) 0.0125(9) 0.0014(9) O15 0.0487(9) 0.0609(11) 0.0385(9) 0.0071(8) 0.0177(7) -0.0043(8) N16 0.0308(8) 0.0280(8) 0.0348(9) 0.0003(7) 0.0129(7) -0.0012(7) O17 0.0402(8) 0.0301(7) 0.0418(8) 0.0014(6) 0.0122(7) -0.0071(6) C41 0.0314(10) 0.0398(12) 0.0339(11) 0.0004(9) 0.0087(9) 0.0054(9) O41 0.0509(9) 0.0355(9) 0.0710(12) 0.0018(8) 0.0262(9) 0.0069(7) O42 0.0405(8) 0.0434(9) 0.0692(11) 0.0000(8) 0.0303(8) 0.0070(7) C42 0.0401(12) 0.0564(15) 0.0557(15) -0.0012(12) 0.0234(11) 0.0147(11) C43 0.0678(17) 0.080(2) 0.096(2) 0.0126(18) 0.0565(18) 0.0168(16) C51 0.0399(11) 0.0409(13) 0.0450(13) -0.0042(11) 0.0157(10) -0.0073(10) O51 0.0679(12) 0.0461(11) 0.0736(13) -0.0188(10) 0.0041(10) -0.0029(9) O52 0.0550(10) 0.0513(10) 0.0449(9) -0.0040(8) -0.0010(8) -0.0029(9) C52 0.0477(14) 0.080(2) 0.0441(14) -0.0094(14) 0.0034(12) -0.0088(14) _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 C1 N2 1.422(3) . yes C1 O17 1.427(2) . yes C1 N16 1.492(2) . yes C1 C12 1.556(3) . yes N2 C3 1.485(3) . yes N2 H2 0.83(2) . ? C3 C31 1.520(3) . ? C3 C4 1.552(3) . yes C3 H3 0.9800 . ? C31 H311 0.9600 . ? C31 H312 0.9600 . ? C31 H313 0.9600 . ? C4 C41 1.524(3) . ? C4 C5 1.565(3) . yes C4 H4 0.9800 . ? C5 N16 1.466(2) . yes C5 C6 1.521(3) . yes C5 H5 0.9800 . ? C6 C7 1.398(3) . ? C6 C11 1.400(3) . yes C7 C8 1.381(3) . ? C7 H7 0.9300 . ? C8 C9 1.387(3) . ? C8 H8 0.9300 . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.396(3) . ? C10 H10 0.9300 . ? C11 C12 1.524(3) . yes C12 C13 1.567(3) . yes C12 H12 0.9800 . ? C13 C14 1.548(3) . yes C13 H131 0.9700 . ? C13 H132 0.9700 . ? C14 O17 1.445(2) . yes C14 C51 1.512(3) . ? C14 C15 1.551(3) . yes C15 O15 1.212(2) . yes C15 N16 1.377(3) . yes C41 O41 1.207(3) . ? C41 O42 1.336(2) . ? O42 C42 1.461(2) . ? C42 C43 1.491(4) . ? C42 H421 0.9700 . ? C42 H422 0.9700 . ? C43 H431 0.9600 . ? C43 H432 0.9600 . ? C43 H433 0.9600 . ? C51 O51 1.198(3) . ? C51 O52 1.324(3) . ? O52 C52 1.459(3) . ? C52 H521 0.9600 . ? C52 H522 0.9600 . ? C52 H523 0.9600 . ? 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 C1 O17 111.87(16) . . yes N2 C1 N16 113.21(15) . . ? O17 C1 N16 100.71(15) . . yes N2 C1 C12 118.36(17) . . ? O17 C1 C12 105.28(15) . . yes N16 C1 C12 105.66(15) . . yes C1 N2 C3 110.36(16) . . yes C1 N2 H2 109.3(17) . . ? C3 N2 H2 106.5(17) . . ? N2 C3 C31 109.62(18) . . ? N2 C3 C4 112.96(16) . . ? C31 C3 C4 114.08(17) . . ? N2 C3 H3 106.5 . . ? C31 C3 H3 106.5 . . ? C4 C3 H3 106.5 . . ? C3 C31 H311 109.5 . . ? C3 C31 H312 109.5 . . ? H311 C31 H312 109.5 . . ? C3 C31 H313 109.5 . . ? H311 C31 H313 109.5 . . ? H312 C31 H313 109.5 . . ? C41 C4 C3 114.27(17) . . ? C41 C4 C5 108.82(16) . . ? C3 C4 C5 110.73(15) . . ? C41 C4 H4 107.6 . . ? C3 C4 H4 107.6 . . ? C5 C4 H4 107.6 . . ? N16 C5 C6 109.06(15) . . ? N16 C5 C4 107.14(15) . . ? C6 C5 C4 111.35(16) . . ? N16 C5 H5 109.7 . . ? C6 C5 H5 109.7 . . ? C4 C5 H5 109.7 . . ? C7 C6 C11 119.84(19) . . ? C7 C6 C5 120.74(17) . . ? C11 C6 C5 119.39(17) . . ? C8 C7 C6 120.78(19) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.7(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 121.7(2) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C6 118.25(19) . . ? C10 C11 C12 120.15(17) . . ? C6 C11 C12 121.48(17) . . ? C11 C12 C1 114.39(15) . . ? C11 C12 C13 111.41(17) . . ? C1 C12 C13 99.43(15) . . yes C11 C12 H12 110.4 . . ? C1 C12 H12 110.4 . . ? C13 C12 H12 110.4 . . ? C14 C13 C12 101.43(15) . . yes C14 C13 H131 111.5 . . ? C12 C13 H131 111.5 . . ? C14 C13 H132 111.5 . . ? C12 C13 H132 111.5 . . ? H131 C13 H132 109.3 . . ? O17 C14 C51 112.87(17) . . ? O17 C14 C13 101.08(16) . . yes C51 C14 C13 118.70(17) . . ? O17 C14 C15 102.23(15) . . yes C51 C14 C15 114.67(17) . . ? C13 C14 C15 105.23(16) . . ? O15 C15 N16 128.36(19) . . yes O15 C15 C14 128.86(19) . . ? N16 C15 C14 102.65(16) . . yes C15 N16 C5 123.49(16) . . ? C15 N16 C1 105.95(15) . . yes C5 N16 C1 112.36(15) . . ? C1 O17 C14 96.19(14) . . yes O41 C41 O42 124.0(2) . . ? O41 C41 C4 126.3(2) . . ? O42 C41 C4 109.72(18) . . ? C41 O42 C42 118.39(17) . . ? O42 C42 C43 106.0(2) . . ? O42 C42 H421 110.5 . . ? C43 C42 H421 110.5 . . ? O42 C42 H422 110.5 . . ? C43 C42 H422 110.5 . . ? H421 C42 H422 108.7 . . ? C42 C43 H431 109.5 . . ? C42 C43 H432 109.5 . . ? H431 C43 H432 109.5 . . ? C42 C43 H433 109.5 . . ? H431 C43 H433 109.5 . . ? H432 C43 H433 109.5 . . ? O51 C51 O52 126.1(2) . . ? O51 C51 C14 123.8(2) . . ? O52 C51 C14 110.07(19) . . ? C51 O52 C52 117.3(2) . . ? O52 C52 H521 109.5 . . ? O52 C52 H522 109.5 . . ? H521 C52 H522 109.5 . . ? O52 C52 H523 109.5 . . ? H521 C52 H523 109.5 . . ? H522 C52 H523 109.5 . . ? 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 O17 C1 N2 C3 -169.50(15) . . . . yes N16 C1 N2 C3 -56.5(2) . . . . ? C12 C1 N2 C3 67.9(2) . . . . ? C1 N2 C3 C31 -179.37(17) . . . . yes C1 N2 C3 C4 52.2(2) . . . . ? N2 C3 C4 C41 71.9(2) . . . . ? C31 C3 C4 C41 -54.2(2) . . . . ? N2 C3 C4 C5 -51.4(2) . . . . ? C31 C3 C4 C5 -177.45(18) . . . . yes C41 C4 C5 N16 -73.51(19) . . . . ? C3 C4 C5 N16 52.9(2) . . . . ? C41 C4 C5 C6 167.32(16) . . . . yes C3 C4 C5 C6 -66.3(2) . . . . ? N16 C5 C6 C7 152.10(19) . . . . ? C4 C5 C6 C7 -89.9(2) . . . . ? N16 C5 C6 C11 -30.1(2) . . . . ? C4 C5 C6 C11 87.9(2) . . . . ? C11 C6 C7 C8 -0.4(3) . . . . ? C5 C6 C7 C8 177.4(2) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? C7 C8 C9 C10 1.0(4) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C9 C10 C11 C6 -1.8(3) . . . . ? C9 C10 C11 C12 174.2(2) . . . . ? C7 C6 C11 C10 1.8(3) . . . . ? C5 C6 C11 C10 -176.01(19) . . . . ? C7 C6 C11 C12 -174.15(19) . . . . ? C5 C6 C11 C12 8.0(3) . . . . yes C10 C11 C12 C1 169.57(19) . . . . ? C6 C11 C12 C1 -14.5(3) . . . . yes C10 C11 C12 C13 -78.6(2) . . . . ? C6 C11 C12 C13 97.3(2) . . . . ? N2 C1 C12 C11 -86.6(2) . . . . ? O17 C1 C12 C11 147.56(16) . . . . ? N16 C1 C12 C11 41.5(2) . . . . ? N2 C1 C12 C13 154.65(17) . . . . ? O17 C1 C12 C13 28.77(18) . . . . ? N16 C1 C12 C13 -77.29(17) . . . . ? C11 C12 C13 C14 -113.71(17) . . . . ? C1 C12 C13 C14 7.27(18) . . . . yes C12 C13 C14 O17 -40.63(18) . . . . ? C12 C13 C14 C51 -164.59(18) . . . . ? C12 C13 C14 C15 65.45(18) . . . . ? O17 C14 C15 O15 -157.8(2) . . . . ? C51 C14 C15 O15 -35.3(3) . . . . ? C13 C14 C15 O15 96.9(2) . . . . ? O17 C14 C15 N16 26.11(19) . . . . ? C51 C14 C15 N16 148.60(18) . . . . ? C13 C14 C15 N16 -79.12(18) . . . . ? O15 C15 N16 C5 -36.5(3) . . . . ? C14 C15 N16 C5 139.57(17) . . . . ? O15 C15 N16 C1 -168.1(2) . . . . ? C14 C15 N16 C1 8.00(19) . . . . yes C6 C5 N16 C15 -66.2(2) . . . . ? C4 C5 N16 C15 173.15(16) . . . . yes C6 C5 N16 C1 62.7(2) . . . . ? C4 C5 N16 C1 -57.91(19) . . . . ? N2 C1 N16 C15 -159.83(17) . . . . ? O17 C1 N16 C15 -40.26(18) . . . . ? C12 C1 N16 C15 69.10(18) . . . . ? N2 C1 N16 C5 62.6(2) . . . . ? O17 C1 N16 C5 -177.84(14) . . . . yes C12 C1 N16 C5 -68.48(18) . . . . ? N2 C1 O17 C14 175.21(16) . . . . yes N16 C1 O17 C14 54.67(16) . . . . ? C12 C1 O17 C14 -54.99(17) . . . . ? C51 C14 O17 C1 -173.48(17) . . . . ? C13 C14 O17 C1 58.66(16) . . . . ? C15 C14 O17 C1 -49.77(17) . . . . ? C3 C4 C41 O41 -23.3(3) . . . . ? C5 C4 C41 O41 101.0(2) . . . . ? C3 C4 C41 O42 157.43(17) . . . . ? C5 C4 C41 O42 -78.3(2) . . . . ? O41 C41 O42 C42 2.6(3) . . . . ? C4 C41 O42 C42 -178.10(17) . . . . ? C41 O42 C42 C43 -174.2(2) . . . . ? O17 C14 C51 O51 27.0(3) . . . . ? C13 C14 C51 O51 144.9(2) . . . . ? C15 C14 C51 O51 -89.5(3) . . . . ? O17 C14 C51 O52 -153.64(17) . . . . ? C13 C14 C51 O52 -35.7(3) . . . . ? C15 C14 C51 O52 89.8(2) . . . . ? O51 C51 O52 C52 3.8(4) . . . . ? C14 C51 O52 C52 -175.60(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.246 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.039