# Supplementary Material (ESI) for Catalysis Science & Technology # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Cat.Sci.Tech. _journal_coden_cambridge 1486 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name C.Redshaw C.Lorber E.Despagnet-Ayoub L.Vendier A.Arbaoui _publ_contact_author_name 'Redshaw, Carl' _publ_contact_author_email carl.redshaw@uea.ac.uk data_3 _database_code_depnum_ccdc_archive 'CCDC 802723' #TrackingRef '- CL1184_2.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H34 N1 O4 V1' _chemical_formula_sum 'C24 H34 N O4 V' _chemical_formula_weight 451.46 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.4832(12) _cell_length_b 11.5025(16) _cell_length_c 24.140(3) _cell_angle_alpha 90 _cell_angle_beta 94.873(12) _cell_angle_gamma 90 _cell_volume 2347.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180 _cell_measurement_reflns_used 2431 _cell_measurement_theta_min 2.6324 _cell_measurement_theta_max 27.999 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.27 (release 29-05-2008 CrysAlis171 .NET) (compiled May 29 2008,13:12:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.984 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _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 'Oxford Diffraction Xcalibur' _diffrn_measurement_method \w-\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_orient_matrix_ub_11 -0.0078759959 _diffrn_orient_matrix_ub_12 -0.0005810484 _diffrn_orient_matrix_ub_13 0.0291892969 _diffrn_orient_matrix_ub_21 -0.0833417934 _diffrn_orient_matrix_ub_22 0.007749268 _diffrn_orient_matrix_ub_23 -0.0052735623 _diffrn_orient_matrix_ub_31 -0.0104704705 _diffrn_orient_matrix_ub_32 -0.0615616867 _diffrn_orient_matrix_ub_33 -0.0009645225 _diffrn_reflns_av_R_equivalents 0.1848 _diffrn_reflns_av_unetI/netI 0.192 _diffrn_reflns_number 16030 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4289 _reflns_number_gt 1908 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0461P)^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_number_reflns 4289 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1833 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.396 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.087 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.5125(5) -0.1184(4) 0.6479(2) 0.0261(12) Uani 1 1 d . . . H1A H 0.6128 -0.0778 0.6537 0.031 Uiso 1 1 calc R . . H1B H 0.4894 -0.1279 0.6081 0.031 Uiso 1 1 calc R . . C2 C 0.5328(6) -0.2379(4) 0.6736(2) 0.0390(15) Uani 1 1 d . . . H2A H 0.439 -0.2842 0.6638 0.047 Uiso 1 1 calc R . . H2B H 0.546 -0.2311 0.7138 0.047 Uiso 1 1 calc R . . C3 C 0.6762(7) -0.2973(4) 0.6530(2) 0.0496(17) Uani 1 1 d . . . H3A H 0.6643 -0.3016 0.6131 0.074 Uiso 1 1 calc R . . H3B H 0.6856 -0.3743 0.6682 0.074 Uiso 1 1 calc R . . H3C H 0.7696 -0.2535 0.6646 0.074 Uiso 1 1 calc R . . C4 C 0.5567(6) 0.2886(4) 0.5636(2) 0.0354(14) Uani 1 1 d . . . H4 H 0.6375 0.2301 0.5744 0.042 Uiso 1 1 calc R . . C5 C 0.5165(7) 0.2812(5) 0.5019(2) 0.0487(16) Uani 1 1 d . . . H5A H 0.4754 0.2053 0.4925 0.073 Uiso 1 1 calc R . . H5B H 0.6101 0.2947 0.483 0.073 Uiso 1 1 calc R . . H5C H 0.4384 0.3388 0.4906 0.073 Uiso 1 1 calc R . . C6 C 0.6192(7) 0.4064(4) 0.5820(3) 0.063(2) Uani 1 1 d . . . H6A H 0.5378 0.4637 0.5746 0.094 Uiso 1 1 calc R . . H6B H 0.7086 0.4258 0.5619 0.094 Uiso 1 1 calc R . . H6C H 0.651 0.4047 0.6211 0.094 Uiso 1 1 calc R . . C7 C 0.2323(6) -0.0456(4) 0.5543(2) 0.0244(12) Uani 1 1 d . . . C8 C 0.1839(6) -0.0692(4) 0.4981(2) 0.0266(13) Uani 1 1 d . . . C9 C 0.0864(6) -0.1627(4) 0.4856(2) 0.0303(13) Uani 1 1 d . . . H9 H 0.0534 -0.1773 0.4485 0.036 Uiso 1 1 calc R . . C10 C 0.0352(6) -0.2360(4) 0.5258(2) 0.0302(13) Uani 1 1 d . . . C11 C 0.0876(6) -0.2134(4) 0.5804(2) 0.0260(12) Uani 1 1 d . . . H11 H 0.0592 -0.2638 0.608 0.031 Uiso 1 1 calc R . . C12 C 0.1815(5) -0.1176(4) 0.5956(2) 0.0253(12) Uani 1 1 d . . . C13 C 0.2272(6) -0.0945(4) 0.6567(2) 0.0287(13) Uani 1 1 d . . . H13A H 0.1496 -0.0425 0.6705 0.034 Uiso 1 1 calc R . . H13B H 0.2229 -0.1672 0.6768 0.034 Uiso 1 1 calc R . . C14 C 0.2428(6) 0.0070(4) 0.4537(2) 0.0354(14) Uani 1 1 d . . . H14A H 0.3556 -0.0003 0.4541 0.053 Uiso 1 1 calc R . . H14B H 0.2157 0.0864 0.4606 0.053 Uiso 1 1 calc R . . H14C H 0.1946 -0.0166 0.418 0.053 Uiso 1 1 calc R . . C15 C -0.0706(6) -0.3372(4) 0.5099(2) 0.0425(15) Uani 1 1 d . . . H15A H -0.1549 -0.3122 0.4835 0.064 Uiso 1 1 calc R . . H15B H -0.1142 -0.3673 0.5424 0.064 Uiso 1 1 calc R . . H15C H -0.0105 -0.3969 0.4935 0.064 Uiso 1 1 calc R . . C16 C 0.6484(6) 0.1017(4) 0.7179(2) 0.0265(13) Uani 1 1 d . . . C17 C 0.8023(6) 0.1404(4) 0.7349(2) 0.0294(13) Uani 1 1 d . . . C18 C 0.8778(6) 0.0919(4) 0.7832(2) 0.0348(14) Uani 1 1 d . . . H18 H 0.9795 0.117 0.7948 0.042 Uiso 1 1 calc R . . C19 C 0.8091(7) 0.0085(4) 0.8146(2) 0.0322(13) Uani 1 1 d . . . C20 C 0.6588(6) -0.0282(4) 0.7958(2) 0.0318(13) Uani 1 1 d . . . H20 H 0.6111 -0.0858 0.8156 0.038 Uiso 1 1 calc R . . C21 C 0.5758(6) 0.0171(4) 0.7486(2) 0.0252(12) Uani 1 1 d . . . C22 C 0.4127(6) -0.0238(4) 0.7297(2) 0.0270(12) Uani 1 1 d . . . H22A H 0.3924 -0.096 0.7485 0.032 Uiso 1 1 calc R . . H22B H 0.3369 0.0332 0.7406 0.032 Uiso 1 1 calc R . . C23 C 0.8811(6) 0.2300(4) 0.7019(2) 0.0391(14) Uani 1 1 d . . . H23A H 0.8174 0.2991 0.6991 0.059 Uiso 1 1 calc R . . H23B H 0.8934 0.2004 0.6653 0.059 Uiso 1 1 calc R . . H23C H 0.9832 0.2481 0.7201 0.059 Uiso 1 1 calc R . . C24 C 0.8919(7) -0.0389(4) 0.8668(2) 0.0480(16) Uani 1 1 d . . . H24A H 1.0041 -0.0304 0.8656 0.072 Uiso 1 1 calc R . . H24B H 0.8663 -0.1198 0.8702 0.072 Uiso 1 1 calc R . . H24C H 0.8584 0.0029 0.8981 0.072 Uiso 1 1 calc R . . N1 N 0.3872(4) -0.0426(3) 0.66882(16) 0.0222(10) Uani 1 1 d . . . O1 O 0.4202(4) 0.2645(2) 0.59203(14) 0.0320(9) Uani 1 1 d . . . O2 O 0.3290(4) 0.0463(3) 0.56641(13) 0.0293(9) Uani 1 1 d . . . O3 O 0.5735(4) 0.1469(3) 0.67065(14) 0.0316(9) Uani 1 1 d . . . O4 O 0.2345(4) 0.1661(3) 0.65950(15) 0.0428(10) Uani 1 1 d . . . V1 V 0.38404(10) 0.13326(7) 0.62810(4) 0.0272(3) Uani 1 1 d . . . 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 0.031(3) 0.024(3) 0.025(3) -0.003(2) 0.007(2) -0.001(2) C2 0.047(4) 0.030(3) 0.042(4) 0.007(3) 0.013(3) 0.004(3) C3 0.056(4) 0.042(3) 0.052(5) 0.009(3) 0.007(3) 0.019(3) C4 0.028(3) 0.029(3) 0.050(4) 0.002(3) 0.005(3) 0.003(2) C5 0.050(4) 0.056(4) 0.042(5) 0.007(3) 0.013(3) 0.003(3) C6 0.075(5) 0.050(4) 0.067(5) -0.004(3) 0.030(4) -0.025(3) C7 0.032(3) 0.021(3) 0.021(3) 0.002(2) 0.009(2) 0.007(2) C8 0.032(3) 0.027(3) 0.020(4) 0.001(3) 0.002(2) 0.012(2) C9 0.031(3) 0.034(3) 0.025(3) -0.008(3) -0.001(2) 0.005(3) C10 0.034(4) 0.027(3) 0.030(4) 0.001(3) 0.006(3) 0.004(2) C11 0.033(3) 0.027(3) 0.019(3) 0.001(2) 0.007(2) -0.002(2) C12 0.028(3) 0.030(3) 0.017(3) 0.000(3) 0.002(2) -0.001(2) C13 0.034(3) 0.031(3) 0.021(3) 0.000(2) 0.007(2) -0.006(2) C14 0.049(4) 0.038(3) 0.020(3) 0.003(3) 0.008(3) 0.005(3) C15 0.044(4) 0.042(3) 0.040(4) -0.002(3) -0.002(3) -0.007(3) C16 0.033(4) 0.023(3) 0.024(3) -0.008(2) 0.004(3) 0.001(2) C17 0.035(3) 0.021(3) 0.033(4) -0.002(3) 0.008(3) -0.003(3) C18 0.030(3) 0.029(3) 0.045(4) -0.007(3) -0.004(3) 0.001(2) C19 0.039(4) 0.028(3) 0.028(4) -0.003(3) -0.005(3) 0.005(3) C20 0.044(4) 0.027(3) 0.025(4) -0.002(3) 0.004(3) -0.002(3) C21 0.033(3) 0.023(3) 0.020(3) -0.004(2) 0.002(2) -0.005(2) C22 0.036(3) 0.026(3) 0.020(3) -0.001(2) 0.008(2) -0.007(2) C23 0.034(4) 0.047(3) 0.037(4) -0.002(3) 0.005(3) -0.007(3) C24 0.057(4) 0.039(3) 0.045(4) 0.007(3) -0.013(3) -0.003(3) N1 0.027(3) 0.024(2) 0.016(3) 0.0015(19) 0.0018(18) -0.0057(19) O1 0.036(2) 0.0250(18) 0.036(2) 0.0013(17) 0.0123(17) 0.0013(16) O2 0.037(2) 0.0237(17) 0.028(2) 0.0025(16) 0.0033(16) -0.0054(16) O3 0.030(2) 0.036(2) 0.028(2) 0.0093(18) -0.0036(16) -0.0072(17) O4 0.047(3) 0.032(2) 0.053(3) 0.0033(18) 0.0249(19) 0.0089(17) V1 0.0313(5) 0.0229(4) 0.0281(6) 0.0017(5) 0.0074(4) 0.0024(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 1.496(5) . ? C1 C2 1.512(6) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.516(7) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 O1 1.423(5) . ? C4 C5 1.503(7) . ? C4 C6 1.507(7) . ? C4 H4 0.98 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7 O2 1.355(5) . ? C7 C12 1.392(6) . ? C7 C8 1.411(7) . ? C8 C9 1.375(6) . ? C8 C14 1.501(6) . ? C9 C10 1.383(6) . ? C9 H9 0.93 . ? C10 C11 1.379(7) . ? C10 C15 1.501(6) . ? C11 C12 1.390(6) . ? C11 H11 0.93 . ? C12 C13 1.516(6) . ? C13 N1 1.489(6) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 O3 1.361(6) . ? C16 C21 1.397(6) . ? C16 C17 1.406(7) . ? C17 C18 1.399(7) . ? C17 C23 1.494(7) . ? C18 C19 1.381(7) . ? C18 H18 0.93 . ? C19 C20 1.383(7) . ? C19 C24 1.493(7) . ? C20 C21 1.389(6) . ? C20 H20 0.93 . ? C21 C22 1.495(6) . ? C22 N1 1.482(6) . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C23 H23A 0.96 . ? C23 H23B 0.96 . ? C23 H23C 0.96 . ? C24 H24A 0.96 . ? C24 H24B 0.96 . ? C24 H24C 0.96 . ? N1 V1 2.248(4) . ? O1 V1 1.782(3) . ? O2 V1 1.821(3) . ? O3 V1 1.839(3) . ? O4 V1 1.578(3) . ? 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 N1 C1 C2 116.8(4) . . ? N1 C1 H1A 108.1 . . ? C2 C1 H1A 108.1 . . ? N1 C1 H1B 108.1 . . ? C2 C1 H1B 108.1 . . ? H1A C1 H1B 107.3 . . ? C1 C2 C3 110.0(4) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C5 110.0(4) . . ? O1 C4 C6 108.3(4) . . ? C5 C4 C6 112.8(5) . . ? O1 C4 H4 108.6 . . ? C5 C4 H4 108.6 . . ? C6 C4 H4 108.6 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C7 C12 121.9(4) . . ? O2 C7 C8 118.6(4) . . ? C12 C7 C8 119.5(4) . . ? C9 C8 C7 118.8(4) . . ? C9 C8 C14 122.1(5) . . ? C7 C8 C14 119.1(4) . . ? C8 C9 C10 122.9(5) . . ? C8 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 117.4(5) . . ? C11 C10 C15 121.9(5) . . ? C9 C10 C15 120.6(5) . . ? C10 C11 C12 122.1(5) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C11 C12 C7 119.2(4) . . ? C11 C12 C13 119.3(4) . . ? C7 C12 C13 121.5(4) . . ? N1 C13 C12 114.6(4) . . ? N1 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? N1 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 C21 120.9(5) . . ? O3 C16 C17 118.6(4) . . ? C21 C16 C17 120.5(5) . . ? C18 C17 C16 117.7(4) . . ? C18 C17 C23 121.7(5) . . ? C16 C17 C23 120.7(5) . . ? C19 C18 C17 123.3(5) . . ? C19 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? C18 C19 C20 116.9(5) . . ? C18 C19 C24 121.8(5) . . ? C20 C19 C24 121.3(5) . . ? C19 C20 C21 123.0(5) . . ? C19 C20 H20 118.5 . . ? C21 C20 H20 118.5 . . ? C20 C21 C16 118.6(5) . . ? C20 C21 C22 121.6(4) . . ? C16 C21 C22 119.7(5) . . ? N1 C22 C21 113.7(4) . . ? N1 C22 H22A 108.8 . . ? C21 C22 H22A 108.8 . . ? N1 C22 H22B 108.8 . . ? C21 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 N1 C13 107.9(3) . . ? C22 N1 C1 111.8(4) . . ? C13 N1 C1 111.2(3) . . ? C22 N1 V1 107.3(3) . . ? C13 N1 V1 107.3(3) . . ? C1 N1 V1 111.1(3) . . ? C4 O1 V1 125.6(3) . . ? C7 O2 V1 135.5(3) . . ? C16 O3 V1 139.4(3) . . ? O4 V1 O1 102.15(15) . . ? O4 V1 O2 111.32(18) . . ? O1 V1 O2 96.22(15) . . ? O4 V1 O3 114.29(18) . . ? O1 V1 O3 91.27(15) . . ? O2 V1 O3 130.88(15) . . ? O4 V1 N1 89.18(15) . . ? O1 V1 N1 168.40(15) . . ? O2 V1 N1 81.74(14) . . ? O3 V1 N1 81.66(14) . . ?