# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_GaL4 _database_code_depnum_ccdc_archive 'CCDC 921780' #TrackingRef 'web_deposit_cif_file_0_DmitryYufit_1359126946.GaL4.cif' _audit_creation_date 2012-11-12 _audit_creation_method ; Olex2 1.2-beta (compiled Nov 5 2012 18:22:26, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H26 Ga N3 O6' _chemical_formula_sum 'C20 H26 Ga N3 O6' _chemical_formula_weight 474.16 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 7.3312(7) _cell_length_b 13.9288(12) _cell_length_c 19.6479(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2006.3(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4522 _cell_measurement_temperature 100 _cell_measurement_theta_max 57.74 _cell_measurement_theta_min 3.89 _exptl_absorpt_coefficient_mu 2.262 _exptl_absorpt_correction_T_max 0.7514 _exptl_absorpt_correction_T_min 0.5136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0896 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.6835. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0467 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8432 _diffrn_reflns_theta_full 57.47 _diffrn_reflns_theta_max 57.47 _diffrn_reflns_theta_min 4.50 _diffrn_ambient_temperature 100 _diffrn_detector 'Bruker Pt-135' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device 'Bruker Proteum' _diffrn_measurement_device_type 'Bruker Proteum CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2304 _reflns_number_total 2584 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.60A (Bruker, 2009)' _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.849 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.088 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 2584 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0477 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1195 _refine_ls_wR_factor_ref 0.1237 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H1a,H1b} of C1, {H2a,H2b} of C2, H20 of C20, H3 of N3, H6 of C6, H8 of C8, H10 of C10, H16 of C16, H17 of C17, H18 of C18, H19 of C19, {H3a,H3b} of C3, {H5a,H5b} of C5 At 1.5 times of: {H12a,H12b,H12c} of C12, {H13a,H13b,H13c} of C13, {H14a,H14b,H14c} of C14 2.a Ternary CH refined with riding coordinates: N3(H3), C6(H6), C8(H8), C10(H10) 2.b Secondary CH2 refined with riding coordinates: C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b), C5(H5a,H5b) 2.c Aromatic/amide H refined with riding coordinates: C16(H16), C17(H17), C18(H18), C19(H19), C20(H20) 2.d Idealised Me refined as rotating group: C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,H14b,H14c) ; _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 Ga1 Ga 0.94085(7) 0.37343(5) 0.24963(4) 0.0449(2) Uani 1 1 d . . . O1 O 0.9018(5) 0.2450(3) 0.2104(2) 0.0552(10) Uani 1 1 d . . . O2 O 0.7629(5) 0.1047(3) 0.22832(19) 0.0555(11) Uani 1 1 d . . . O3 O 1.1226(5) 0.4017(3) 0.18455(19) 0.0495(10) Uani 1 1 d . . . O4 O 1.2227(6) 0.4922(3) 0.10015(19) 0.0550(10) Uani 1 1 d . . . O5 O 1.1009(5) 0.3182(3) 0.3167(2) 0.0528(10) Uani 1 1 d . . . O6 O 1.2459(6) 0.3432(3) 0.4145(2) 0.0611(12) Uani 1 1 d . . . N1 N 0.6603(7) 0.3501(3) 0.2685(3) 0.0516(13) Uani 1 1 d . . . N2 N 0.8023(6) 0.4898(3) 0.1939(2) 0.0422(11) Uani 1 1 d . . . N3 N 0.9182(6) 0.4803(3) 0.3246(2) 0.0427(11) Uani 1 1 d . . . H3 H 0.9896 0.5308 0.3123 0.051 Uiso 1 1 calc R . . C1 C 0.5627(8) 0.3702(5) 0.2014(3) 0.0524(14) Uani 1 1 d . . . H1A H 0.5356 0.3096 0.1792 0.063 Uiso 1 1 calc R . . H1B H 0.4478 0.4019 0.2109 0.063 Uiso 1 1 calc R . . C2 C 0.6709(8) 0.4309(5) 0.1541(3) 0.0514(15) Uani 1 1 d . . . H2A H 0.5901 0.4726 0.1285 0.062 Uiso 1 1 calc R . . H2B H 0.7365 0.3906 0.1222 0.062 Uiso 1 1 calc R . . C3 C 0.7066(7) 0.5521(4) 0.2447(3) 0.0416(11) Uani 1 1 d . . . H3A H 0.5795 0.5587 0.2318 0.050 Uiso 1 1 calc R . . H3B H 0.7612 0.6156 0.2444 0.050 Uiso 1 1 calc R . . C4 C 0.7185(7) 0.5097(4) 0.3165(3) 0.0416(13) Uani 1 1 d . . . C5 C 0.6033(8) 0.4164(4) 0.3221(3) 0.0479(14) Uani 1 1 d . . . H5A H 0.6213 0.3871 0.3663 0.057 Uiso 1 1 calc R . . H5B H 0.4748 0.4314 0.3170 0.057 Uiso 1 1 calc R . . C6 C 0.6412(9) 0.2449(4) 0.2836(4) 0.0596(16) Uani 1 1 d . . . H6 H 0.5179 0.2249 0.2707 0.071 Uiso 1 1 calc R . . C7 C 0.7774(8) 0.1937(5) 0.2368(3) 0.0551(16) Uani 1 1 d . . . C8 C 0.9429(9) 0.5406(4) 0.1525(3) 0.0467(13) Uani 1 1 d . . . H8 H 0.9859 0.5942 0.1805 0.056 Uiso 1 1 calc R . . C9 C 1.1097(8) 0.4728(4) 0.1429(3) 0.0470(14) Uani 1 1 d . . . C10 C 0.9850(8) 0.4428(5) 0.3900(3) 0.0477(15) Uani 1 1 d . . . H10 H 0.8811 0.4120 0.4126 0.057 Uiso 1 1 calc R . . C11 C 1.1250(8) 0.3625(4) 0.3739(3) 0.0500(14) Uani 1 1 d . . . C12 C 0.6725(10) 0.2166(5) 0.3564(4) 0.0681(19) Uani 1 1 d . . . H12A H 0.7890 0.2402 0.3712 0.102 Uiso 1 1 calc R . . H12B H 0.6703 0.1479 0.3603 0.102 Uiso 1 1 calc R . . H12C H 0.5783 0.2436 0.3844 0.102 Uiso 1 1 calc R . . C13 C 0.8760(9) 0.5840(5) 0.0875(3) 0.0625(17) Uani 1 1 d . . . H13A H 0.8284 0.5344 0.0586 0.094 Uiso 1 1 calc R . . H13B H 0.9751 0.6158 0.0649 0.094 Uiso 1 1 calc R . . H13C H 0.7815 0.6297 0.0974 0.094 Uiso 1 1 calc R . . C14 C 1.0562(9) 0.5172(4) 0.4377(3) 0.0533(14) Uani 1 1 d . . . H14A H 1.1402 0.5582 0.4140 0.080 Uiso 1 1 calc R . . H14B H 1.1178 0.4865 0.4749 0.080 Uiso 1 1 calc R . . H14C H 0.9566 0.5548 0.4549 0.080 Uiso 1 1 calc R . . C15 C 0.6606(7) 0.5828(4) 0.3699(3) 0.0406(12) Uani 1 1 d . . . C16 C 0.5415(8) 0.5585(4) 0.4230(3) 0.0465(13) Uani 1 1 d . . . H16 H 0.4918 0.4971 0.4248 0.056 Uiso 1 1 calc R . . C17 C 0.4973(7) 0.6242(5) 0.4724(3) 0.0502(15) Uani 1 1 d . . . H17 H 0.4192 0.6064 0.5075 0.060 Uiso 1 1 calc R . . C18 C 0.5673(7) 0.7169(4) 0.4708(3) 0.0442(13) Uani 1 1 d . . . H18 H 0.5358 0.7615 0.5041 0.053 Uiso 1 1 calc R . . C19 C 0.6848(7) 0.7412(4) 0.4187(2) 0.0419(12) Uani 1 1 d . . . H19 H 0.7333 0.8029 0.4169 0.050 Uiso 1 1 calc R . . C20 C 0.7307(7) 0.6759(4) 0.3697(3) 0.0413(12) Uani 1 1 d . . . H20 H 0.8108 0.6941 0.3353 0.050 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 Ga1 0.0322(4) 0.0400(4) 0.0625(4) -0.0076(4) 0.0015(4) 0.0021(2) O1 0.034(2) 0.039(3) 0.093(3) -0.012(2) 0.0057(19) 0.0002(18) O2 0.050(2) 0.040(3) 0.076(3) -0.0127(18) -0.0097(18) 0.0090(18) O3 0.036(2) 0.048(3) 0.065(2) -0.0075(19) -0.0006(17) 0.0035(17) O4 0.053(2) 0.058(3) 0.054(2) -0.0089(19) 0.0080(19) -0.005(2) O5 0.040(2) 0.046(3) 0.071(3) -0.001(2) 0.0011(19) 0.0102(18) O6 0.048(2) 0.058(3) 0.078(3) 0.009(2) -0.013(2) 0.006(2) N1 0.045(3) 0.033(3) 0.076(3) -0.009(2) 0.002(2) -0.004(2) N2 0.030(2) 0.037(3) 0.060(3) -0.009(2) 0.0011(19) -0.001(2) N3 0.027(2) 0.035(3) 0.066(3) -0.005(2) 0.004(2) -0.002(2) C1 0.040(3) 0.049(4) 0.068(3) -0.009(3) -0.008(3) -0.002(3) C2 0.034(3) 0.050(4) 0.070(4) -0.012(3) -0.011(3) 0.004(3) C3 0.035(3) 0.035(3) 0.054(3) -0.008(3) -0.003(3) 0.006(2) C4 0.029(3) 0.035(3) 0.060(3) -0.005(2) 0.002(2) 0.001(2) C5 0.031(3) 0.041(4) 0.072(3) -0.008(3) 0.002(3) -0.004(2) C6 0.049(4) 0.033(4) 0.097(5) -0.009(3) 0.000(3) -0.001(3) C7 0.039(3) 0.052(4) 0.074(4) -0.015(3) -0.008(3) 0.008(3) C8 0.050(3) 0.039(4) 0.051(3) -0.008(2) -0.004(3) 0.008(3) C9 0.045(3) 0.046(4) 0.050(3) -0.014(3) 0.000(3) -0.001(3) C10 0.042(3) 0.047(4) 0.055(3) 0.010(3) 0.001(2) 0.005(3) C11 0.047(3) 0.041(4) 0.063(3) 0.005(3) 0.004(3) -0.004(3) C12 0.069(5) 0.042(4) 0.093(5) -0.007(3) 0.019(4) 0.000(3) C13 0.054(4) 0.067(5) 0.066(4) -0.006(3) 0.001(3) 0.002(3) C14 0.048(3) 0.048(4) 0.064(3) -0.002(3) -0.007(3) 0.004(3) C15 0.033(3) 0.038(3) 0.050(3) 0.004(2) -0.005(2) 0.002(2) C16 0.039(3) 0.036(4) 0.064(3) 0.007(3) 0.008(3) 0.000(3) C17 0.050(4) 0.052(4) 0.048(3) 0.006(3) 0.008(2) -0.004(3) C18 0.038(3) 0.037(3) 0.057(3) -0.004(2) 0.001(3) -0.001(2) C19 0.041(3) 0.037(3) 0.048(3) 0.004(2) -0.002(2) -0.005(3) C20 0.037(3) 0.036(3) 0.050(3) 0.000(2) 0.000(2) -0.002(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 Ga1 O1 1.969(4) . ? Ga1 O3 1.888(4) . ? Ga1 O5 1.926(4) . ? Ga1 N1 2.115(5) . ? Ga1 N2 2.203(5) . ? Ga1 N3 2.101(4) . ? O1 C7 1.270(7) . ? O2 C7 1.255(8) . ? O3 C9 1.288(7) . ? O4 C9 1.211(7) . ? O5 C11 1.294(7) . ? O6 C11 1.221(7) . ? N1 C1 1.526(7) . ? N1 C5 1.461(7) . ? N1 C6 1.501(8) . ? N2 C2 1.487(7) . ? N2 C3 1.497(7) . ? N2 C8 1.492(8) . ? N3 H3 0.9100 . ? N3 C4 1.528(7) . ? N3 C10 1.472(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.486(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.533(8) . ? C4 C5 1.554(8) . ? C4 C15 1.522(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6 0.9800 . ? C6 C7 1.533(9) . ? C6 C12 1.503(10) . ? C8 H8 0.9800 . ? C8 C9 1.557(8) . ? C8 C13 1.494(8) . ? C10 H10 0.9800 . ? C10 C11 1.550(8) . ? C10 C14 1.492(8) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.401(7) . ? C15 C20 1.396(8) . ? C16 H16 0.9300 . ? C16 C17 1.373(8) . ? C17 H17 0.9300 . ? C17 C18 1.390(8) . ? C18 H18 0.9300 . ? C18 C19 1.380(7) . ? C19 H19 0.9300 . ? C19 C20 1.367(8) . ? C20 H20 0.9300 . ? 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 O1 Ga1 N1 77.75(17) . . ? O1 Ga1 N2 114.01(18) . . ? O1 Ga1 N3 155.08(18) . . ? O3 Ga1 O1 91.52(17) . . ? O3 Ga1 O5 96.72(17) . . ? O3 Ga1 N1 146.83(18) . . ? O3 Ga1 N2 80.55(16) . . ? O3 Ga1 N3 112.53(17) . . ? O5 Ga1 O1 89.65(18) . . ? O5 Ga1 N1 114.27(19) . . ? O5 Ga1 N2 156.17(17) . . ? O5 Ga1 N3 81.43(18) . . ? N1 Ga1 N2 75.64(18) . . ? N3 Ga1 N1 84.78(17) . . ? N3 Ga1 N2 77.91(17) . . ? C7 O1 Ga1 117.1(4) . . ? C9 O3 Ga1 122.6(3) . . ? C11 O5 Ga1 119.2(4) . . ? C1 N1 Ga1 106.0(3) . . ? C5 N1 Ga1 107.9(3) . . ? C5 N1 C1 111.9(4) . . ? C5 N1 C6 116.6(5) . . ? C6 N1 Ga1 106.0(4) . . ? C6 N1 C1 107.8(4) . . ? C2 N2 Ga1 98.9(3) . . ? C2 N2 C3 111.5(4) . . ? C2 N2 C8 114.9(4) . . ? C3 N2 Ga1 108.2(3) . . ? C8 N2 Ga1 107.6(3) . . ? C8 N2 C3 114.3(4) . . ? Ga1 N3 H3 108.4 . . ? C4 N3 Ga1 101.2(3) . . ? C4 N3 H3 108.4 . . ? C10 N3 Ga1 109.5(3) . . ? C10 N3 H3 108.4 . . ? C10 N3 C4 120.3(4) . . ? N1 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C2 C1 N1 113.2(5) . . ? C2 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? N2 C2 H2A 109.8 . . ? N2 C2 H2B 109.8 . . ? C1 C2 N2 109.3(5) . . ? C1 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? N2 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? N2 C3 C4 111.3(4) . . ? H3A C3 H3B 108.0 . . ? C4 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? N3 C4 C3 104.7(4) . . ? N3 C4 C5 106.8(4) . . ? C3 C4 C5 110.8(4) . . ? C15 C4 N3 112.1(4) . . ? C15 C4 C3 111.2(4) . . ? C15 C4 C5 111.1(5) . . ? N1 C5 C4 108.8(4) . . ? N1 C5 H5A 109.9 . . ? N1 C5 H5B 109.9 . . ? C4 C5 H5A 109.9 . . ? C4 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N1 C6 H6 108.2 . . ? N1 C6 C7 106.0(5) . . ? C7 C6 H6 108.2 . . ? C12 C6 N1 115.4(5) . . ? C12 C6 H6 108.2 . . ? C12 C6 C7 110.5(6) . . ? O1 C7 C6 116.8(6) . . ? O2 C7 O1 124.2(5) . . ? O2 C7 C6 118.9(6) . . ? N2 C8 H8 106.1 . . ? N2 C8 C9 108.7(4) . . ? N2 C8 C13 115.6(5) . . ? C9 C8 H8 106.1 . . ? C13 C8 H8 106.1 . . ? C13 C8 C9 113.6(5) . . ? O3 C9 C8 116.6(5) . . ? O4 C9 O3 124.2(5) . . ? O4 C9 C8 119.1(5) . . ? N3 C10 H10 107.0 . . ? N3 C10 C11 107.4(4) . . ? N3 C10 C14 114.7(5) . . ? C11 C10 H10 107.0 . . ? C14 C10 H10 107.0 . . ? C14 C10 C11 113.4(5) . . ? O5 C11 C10 115.5(5) . . ? O6 C11 O5 124.1(6) . . ? O6 C11 C10 120.4(5) . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C4 121.7(5) . . ? C20 C15 C4 121.1(5) . . ? C20 C15 C16 117.1(5) . . ? C15 C16 H16 119.6 . . ? C17 C16 C15 120.8(5) . . ? C17 C16 H16 119.6 . . ? C16 C17 H17 119.5 . . ? C16 C17 C18 121.1(5) . . ? C18 C17 H17 119.5 . . ? C17 C18 H18 120.8 . . ? C19 C18 C17 118.4(5) . . ? C19 C18 H18 120.8 . . ? C18 C19 H19 119.6 . . ? C20 C19 C18 120.9(5) . . ? C20 C19 H19 119.6 . . ? C15 C20 H20 119.1 . . ? C19 C20 C15 121.7(5) . . ? C19 C20 H20 119.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O2 0.91 2.23 3.090(6) 156.8 4_755