# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_120510_s1_lxh _audit_creation_date 2012-05-10 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H26 N4 O5' _chemical_formula_sum 'C21 H26 N4 O5' _chemical_formula_weight 414.46 _chemical_melting_point ? _chemical_oxdiff_formula C12H12N4O6 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.4737(3) _cell_length_b 16.6247(5) _cell_length_c 28.3411(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.637(2) _cell_angle_gamma 90.00 _cell_volume 3984.5(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2711 _cell_measurement_temperature 135.00(10) _cell_measurement_theta_max 29.2194 _cell_measurement_theta_min 2.8749 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87895 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1760 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_unetI/netI 0.0357 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 7866 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.88 _diffrn_ambient_temperature 135.00(10) _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -93.00 -33.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.0486 178.0000 -150.0000 200 #__ type_ start__ end____ width___ exp.time_ 2 omega -73.00 -19.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.0486 123.0000 126.0000 180 #__ type_ start__ end____ width___ exp.time_ 3 omega -24.00 75.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 19.0000 120.0000 330 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0105187000 _diffrn_orient_matrix_UB_12 -0.0422165000 _diffrn_orient_matrix_UB_13 0.0019451000 _diffrn_orient_matrix_UB_21 -0.0034872000 _diffrn_orient_matrix_UB_22 0.0027784000 _diffrn_orient_matrix_UB_23 0.0248854000 _diffrn_orient_matrix_UB_31 -0.0831591000 _diffrn_orient_matrix_UB_32 -0.0054570000 _diffrn_orient_matrix_UB_33 -0.0023884000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3274 _reflns_number_total 4031 _reflns_odcompleteness_completeness 98.68 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.202 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.053 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 275 _refine_ls_number_reflns 4031 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0405 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+1.7038P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.1014 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O2 O 0.98091(12) 0.23771(6) 0.55844(4) 0.0220(2) Uani 1 1 d . . . O4 O 0.99899(12) 0.00147(6) 0.59792(4) 0.0221(2) Uani 1 1 d . . . O5 O 1.80021(13) 0.03952(6) 0.22356(4) 0.0275(3) Uani 1 1 d . . . N1 N 1.36284(14) 0.11196(7) 0.45384(4) 0.0195(3) Uani 1 1 d . . . H1 H 1.3945 0.1622 0.4570 0.023 Uiso 1 1 calc R . . O1 O 1.36971(12) 0.00060(6) 0.40630(4) 0.0230(3) Uani 1 1 d . . . N2 N 1.49399(14) 0.11683(7) 0.38642(4) 0.0188(3) Uani 1 1 d . . . H2 H 1.5077 0.1674 0.3949 0.023 Uiso 1 1 calc R . . N4 N 1.83002(15) 0.19746(8) 0.21046(5) 0.0260(3) Uani 1 1 d . . . H4 H 1.8454 0.1478 0.2010 0.031 Uiso 1 1 calc R . . C2 C 1.27088(16) 0.08021(9) 0.48953(5) 0.0168(3) Uani 1 1 d . . . O3 O 1.73104(15) 0.27758(7) 0.26480(4) 0.0351(3) Uani 1 1 d . . . C3 C 1.16487(16) 0.13064(8) 0.51029(5) 0.0161(3) Uani 1 1 d . . . H3 H 1.1549 0.1847 0.4996 0.019 Uiso 1 1 calc R . . N3 N 0.82992(13) 0.13706(7) 0.58380(4) 0.0190(3) Uani 1 1 d . . . H3A H 0.8212 0.0849 0.5883 0.023 Uiso 1 1 calc R . . C4 C 1.07234(16) 0.10462(8) 0.54632(5) 0.0153(3) Uani 1 1 d . . . C6 C 1.19753(16) -0.02552(9) 0.54170(5) 0.0185(3) Uani 1 1 d . . . H6 H 1.2098 -0.0794 0.5525 0.022 Uiso 1 1 calc R . . C15 C 0.95723(16) 0.16447(9) 0.56401(5) 0.0162(3) Uani 1 1 d . . . C5 C 1.08982(16) 0.02477(9) 0.56218(5) 0.0166(3) Uani 1 1 d . . . C11 C 1.72342(17) 0.05576(9) 0.26375(5) 0.0204(3) Uani 1 1 d . . . C7 C 1.28690(16) 0.00174(9) 0.50584(5) 0.0184(3) Uani 1 1 d . . . H7 H 1.3598 -0.0335 0.4923 0.022 Uiso 1 1 calc R . . C10 C 1.69948(16) 0.13678(9) 0.27574(5) 0.0180(3) Uani 1 1 d . . . C9 C 1.61785(16) 0.15296(9) 0.31582(5) 0.0174(3) Uani 1 1 d . . . H9 H 1.5974 0.2074 0.3235 0.021 Uiso 1 1 calc R . . C13 C 1.59246(18) 0.01326(9) 0.33307(5) 0.0224(3) Uani 1 1 d . . . H13 H 1.5584 -0.0290 0.3526 0.027 Uiso 1 1 calc R . . C19 C 1.75351(17) 0.20967(9) 0.24978(5) 0.0205(3) Uani 1 1 d . . . C1 C 1.40647(16) 0.07081(9) 0.41482(5) 0.0170(3) Uani 1 1 d . . . C8 C 1.56521(16) 0.09288(9) 0.34493(5) 0.0172(3) Uani 1 1 d . . . C14 C 1.00557(18) -0.08047(9) 0.61279(6) 0.0238(3) Uani 1 1 d . . . H14A H 0.9852 -0.1156 0.5853 0.036 Uiso 1 1 calc R . . H14B H 0.9254 -0.0900 0.6356 0.036 Uiso 1 1 calc R . . H14C H 1.1107 -0.0921 0.6277 0.036 Uiso 1 1 calc R . . C16 C 0.70387(17) 0.18947(9) 0.59845(5) 0.0204(3) Uani 1 1 d . . . H16A H 0.7484 0.2432 0.6064 0.024 Uiso 1 1 calc R . . H16B H 0.6603 0.1671 0.6273 0.024 Uiso 1 1 calc R . . C12 C 1.66966(18) -0.00444(9) 0.29255(6) 0.0242(3) Uani 1 1 d . . . H12 H 1.6860 -0.0591 0.2844 0.029 Uiso 1 1 calc R . . C18 C 1.8114(2) -0.04270(10) 0.20911(6) 0.0302(4) Uani 1 1 d . . . H18A H 1.8690 -0.0457 0.1803 0.045 Uiso 1 1 calc R . . H18B H 1.7049 -0.0649 0.2029 0.045 Uiso 1 1 calc R . . H18C H 1.8678 -0.0738 0.2343 0.045 Uiso 1 1 calc R . . C20 C 1.88846(19) 0.26361(10) 0.18289(6) 0.0274(4) Uani 1 1 d . . . H20A H 1.9770 0.2442 0.1648 0.033 Uiso 1 1 calc R . . H20B H 1.9297 0.3064 0.2046 0.033 Uiso 1 1 calc R . . C21 C 1.7619(2) 0.29844(12) 0.14914(6) 0.0410(5) Uani 1 1 d . . . H21A H 1.7251 0.2571 0.1263 0.061 Uiso 1 1 calc R . . H21B H 1.8052 0.3440 0.1323 0.061 Uiso 1 1 calc R . . H21C H 1.6730 0.3168 0.1669 0.061 Uiso 1 1 calc R . . C17 C 0.5726(2) 0.19830(12) 0.56049(6) 0.0383(5) Uani 1 1 d . . . H17A H 0.6152 0.2206 0.5319 0.057 Uiso 1 1 calc R . . H17B H 0.4915 0.2345 0.5715 0.057 Uiso 1 1 calc R . . H17C H 0.5257 0.1455 0.5533 0.057 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 O2 0.0278(6) 0.0133(5) 0.0260(6) -0.0010(4) 0.0090(4) -0.0027(4) O4 0.0264(6) 0.0172(6) 0.0238(6) 0.0073(4) 0.0110(4) 0.0018(4) O5 0.0439(7) 0.0164(6) 0.0242(6) -0.0032(5) 0.0173(5) -0.0010(5) N1 0.0246(7) 0.0150(6) 0.0198(6) -0.0014(5) 0.0084(5) -0.0049(5) O1 0.0277(6) 0.0174(6) 0.0249(6) -0.0039(5) 0.0102(4) -0.0073(4) N2 0.0252(7) 0.0134(6) 0.0187(6) -0.0018(5) 0.0086(5) -0.0032(5) N4 0.0380(8) 0.0181(7) 0.0233(7) 0.0005(6) 0.0133(6) -0.0028(6) C2 0.0157(7) 0.0187(8) 0.0163(7) -0.0008(6) 0.0033(5) -0.0040(6) O3 0.0550(8) 0.0170(6) 0.0358(7) -0.0005(5) 0.0219(6) -0.0027(5) C3 0.0192(7) 0.0117(7) 0.0174(7) -0.0001(6) 0.0017(5) -0.0024(6) N3 0.0204(6) 0.0135(6) 0.0239(7) 0.0011(5) 0.0079(5) -0.0002(5) C4 0.0153(7) 0.0152(7) 0.0154(7) -0.0034(6) 0.0007(5) -0.0019(6) C6 0.0190(7) 0.0164(7) 0.0201(7) 0.0021(6) 0.0013(6) 0.0010(6) C15 0.0197(7) 0.0149(7) 0.0141(7) -0.0006(6) 0.0012(5) -0.0022(6) C5 0.0159(7) 0.0184(7) 0.0156(7) 0.0012(6) 0.0019(5) -0.0032(6) C11 0.0240(8) 0.0210(8) 0.0167(7) -0.0021(6) 0.0061(6) 0.0001(6) C7 0.0164(7) 0.0190(8) 0.0199(7) -0.0020(6) 0.0026(5) 0.0005(6) C10 0.0190(7) 0.0182(8) 0.0169(7) -0.0003(6) 0.0013(5) -0.0010(6) C9 0.0199(7) 0.0146(7) 0.0177(7) -0.0019(6) 0.0013(5) -0.0005(6) C13 0.0279(8) 0.0162(8) 0.0242(8) 0.0017(6) 0.0098(6) -0.0021(6) C19 0.0238(8) 0.0179(8) 0.0200(8) -0.0006(6) 0.0028(6) -0.0017(6) C1 0.0159(7) 0.0171(7) 0.0183(7) 0.0010(6) 0.0029(5) -0.0008(6) C8 0.0174(7) 0.0182(7) 0.0163(7) -0.0009(6) 0.0034(5) -0.0008(6) C14 0.0266(8) 0.0184(8) 0.0273(8) 0.0097(7) 0.0081(6) 0.0007(6) C16 0.0212(8) 0.0189(8) 0.0219(8) -0.0028(6) 0.0082(6) 0.0004(6) C12 0.0331(9) 0.0138(8) 0.0267(8) -0.0014(6) 0.0093(6) -0.0008(6) C18 0.0450(10) 0.0192(9) 0.0277(9) -0.0054(7) 0.0133(7) 0.0037(7) C20 0.0364(9) 0.0233(8) 0.0235(8) 0.0022(7) 0.0096(7) -0.0078(7) C21 0.0524(12) 0.0356(10) 0.0336(10) 0.0075(9) -0.0076(8) -0.0160(9) C17 0.0367(10) 0.0436(11) 0.0339(10) -0.0091(9) -0.0040(7) 0.0186(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 O2 C15 1.2456(17) . ? O4 C5 1.3665(17) . ? O4 C14 1.4259(17) . ? O5 C11 1.3740(18) . ? O5 C18 1.4318(19) . ? N1 H1 0.8800 . ? N1 C2 1.4174(18) . ? N1 C1 1.3711(18) . ? O1 C1 1.2281(17) . ? N2 H2 0.8800 . ? N2 C1 1.3633(18) . ? N2 C8 1.4126(18) . ? N4 H4 0.8800 . ? N4 C19 1.340(2) . ? N4 C20 1.454(2) . ? C2 C3 1.387(2) . ? C2 C7 1.388(2) . ? O3 C19 1.2258(19) . ? C3 H3 0.9500 . ? C3 C4 1.395(2) . ? N3 H3A 0.8800 . ? N3 C15 1.3277(18) . ? N3 C16 1.4590(18) . ? C4 C15 1.502(2) . ? C4 C5 1.406(2) . ? C6 H6 0.9500 . ? C6 C5 1.391(2) . ? C6 C7 1.382(2) . ? C11 C10 1.407(2) . ? C11 C12 1.386(2) . ? C7 H7 0.9500 . ? C10 C9 1.393(2) . ? C10 C19 1.504(2) . ? C9 H9 0.9500 . ? C9 C8 1.387(2) . ? C13 H13 0.9500 . ? C13 C8 1.389(2) . ? C13 C12 1.389(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.505(2) . ? C12 H12 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.507(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C5 O4 C14 118.47(12) . . ? C11 O5 C18 117.92(12) . . ? C2 N1 H1 117.3 . . ? C1 N1 H1 117.3 . . ? C1 N1 C2 125.34(12) . . ? C1 N2 H2 116.2 . . ? C1 N2 C8 127.61(12) . . ? C8 N2 H2 116.2 . . ? C19 N4 H4 118.9 . . ? C19 N4 C20 122.11(14) . . ? C20 N4 H4 118.9 . . ? C3 C2 N1 118.54(13) . . ? C3 C2 C7 118.65(13) . . ? C7 C2 N1 122.76(13) . . ? C2 C3 H3 118.9 . . ? C2 C3 C4 122.17(13) . . ? C4 C3 H3 118.9 . . ? C15 N3 H3A 118.5 . . ? C15 N3 C16 122.98(12) . . ? C16 N3 H3A 118.5 . . ? C3 C4 C15 116.49(12) . . ? C3 C4 C5 118.28(13) . . ? C5 C4 C15 125.19(13) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C7 C6 C5 120.95(14) . . ? O2 C15 N3 122.06(13) . . ? O2 C15 C4 119.48(13) . . ? N3 C15 C4 118.42(12) . . ? O4 C5 C4 116.85(13) . . ? O4 C5 C6 123.64(13) . . ? C6 C5 C4 119.51(13) . . ? O5 C11 C10 118.13(13) . . ? O5 C11 C12 122.46(14) . . ? C12 C11 C10 119.41(14) . . ? C2 C7 H7 119.8 . . ? C6 C7 C2 120.44(14) . . ? C6 C7 H7 119.8 . . ? C11 C10 C19 126.88(13) . . ? C9 C10 C11 117.93(14) . . ? C9 C10 C19 115.20(13) . . ? C10 C9 H9 118.6 . . ? C8 C9 C10 122.75(14) . . ? C8 C9 H9 118.6 . . ? C8 C13 H13 120.1 . . ? C8 C13 C12 119.77(14) . . ? C12 C13 H13 120.1 . . ? N4 C19 C10 117.60(13) . . ? O3 C19 N4 121.50(15) . . ? O3 C19 C10 120.89(14) . . ? O1 C1 N1 123.70(13) . . ? O1 C1 N2 123.92(13) . . ? N2 C1 N1 112.38(12) . . ? C9 C8 N2 117.56(13) . . ? C9 C8 C13 118.53(13) . . ? C13 C8 N2 123.82(13) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C16 H16A 109.2 . . ? N3 C16 H16B 109.2 . . ? N3 C16 C17 112.09(13) . . ? H16A C16 H16B 107.9 . . ? C17 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C11 C12 C13 121.56(14) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? O5 C18 H18A 109.5 . . ? O5 C18 H18B 109.5 . . ? O5 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C20 H20A 109.2 . . ? N4 C20 H20B 109.2 . . ? N4 C20 C21 112.26(13) . . ? H20A C20 H20B 107.9 . . ? C21 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _database_code_depnum_ccdc_archive 'CCDC 938513'