# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Fernando Avecilla' _publ_contact_author_email avecil@udc.es loop_ _publ_author_name 'Mannar R. Maurya' 'Manisha Bisht' 'Amit Kumar' 'Fernando Avecilla' 'J. Costa Pessoa' data_ups22mrm _database_code_depnum_ccdc_archive 'CCDC 812058' #TrackingRef 'ups22mrm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N4 O5 V, C H4 O' _chemical_formula_sum 'C23 H28 N4 O6 V' _chemical_formula_weight 507.43 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 11.9158(8) _cell_length_b 16.1483(12) _cell_length_c 12.7891(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.840(4) _cell_angle_gamma 90.00 _cell_volume 2424.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 0.455 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8948 _exptl_absorpt_correction_T_max 0.9560 _exptl_absorpt_process_details 'North et al., 1968' _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_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39550 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 30.54 _reflns_number_total 7395 _reflns_number_gt 6009 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART Apex CCD' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0763P)^2^+0.4317P] 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 0.0160(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7395 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _refine_ls_shift/su_max 0.001 _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 V1 V 0.63466(2) 0.120104(16) 0.89759(2) 0.01329(9) Uani 1 1 d . . . O1 O 0.52960(10) 0.14819(7) 0.95499(9) 0.0174(2) Uani 1 1 d . . . N1 N 0.75595(11) -0.19725(8) 0.91132(11) 0.0174(3) Uani 1 1 d . . . C1 C 0.67488(13) -0.05949(9) 0.90277(12) 0.0152(3) Uani 1 1 d . . . O1W O 0.84373(12) -0.34384(9) 1.00133(12) 0.0303(3) Uani 1 1 d . . . H1O H 0.823(3) -0.300(2) 0.982(3) 0.058(9) Uiso 1 1 d . . . C1W C 0.9453(2) -0.33566(19) 1.0724(3) 0.0744(11) Uani 1 1 d . . . H1W1 H 0.9885 -0.2905 1.0508 0.112 Uiso 1 1 calc R . . H1W2 H 0.9885 -0.3859 1.0734 0.112 Uiso 1 1 calc R . . H1W3 H 0.9291 -0.3249 1.1422 0.112 Uiso 1 1 calc R . . O2 O 0.66323(10) 0.00801(7) 0.95579(9) 0.0169(2) Uani 1 1 d . . . N2 N 0.54253(11) 0.06414(8) 0.76393(10) 0.0155(3) Uani 1 1 d . . . C2 C 0.73209(13) -0.12806(9) 0.95925(13) 0.0159(3) Uani 1 1 d . . . O3 O 0.76902(10) 0.09347(7) 0.81001(9) 0.0184(2) Uani 1 1 d . . . N3 N 0.60994(13) 0.31742(9) 0.67104(12) 0.0198(3) Uani 1 1 d . . . H3N H 0.587(2) 0.3328(18) 0.610(2) 0.051(8) Uiso 1 1 d . . . C3 C 0.72177(13) -0.20423(10) 0.80449(13) 0.0178(3) Uani 1 1 d . . . H3 H 0.7425(17) -0.2527(14) 0.7730(18) 0.025(5) Uiso 1 1 d . . . O4 O 0.76200(10) 0.15773(7) 1.00814(9) 0.0176(2) Uani 1 1 d . . . N4 N 0.63266(11) 0.23308(8) 0.81041(10) 0.0159(3) Uani 1 1 d . . . C4 C 0.65837(13) -0.14502(10) 0.74366(12) 0.0162(3) Uani 1 1 d . . . C5 C 0.63306(13) -0.07072(9) 0.79323(12) 0.0157(3) Uani 1 1 d . . . O5 O 0.65053(12) -0.09573(8) 0.56184(10) 0.0222(3) Uani 1 1 d . . . H5 H 0.711(2) -0.1045(14) 0.544(2) 0.027(6) Uiso 1 1 d . . . C6 C 0.76605(15) -0.12148(10) 1.07712(13) 0.0189(3) Uani 1 1 d . . . H6C H 0.805(2) -0.0694(16) 1.094(2) 0.036(6) Uiso 1 1 d . . . H6B H 0.809(2) -0.1692(16) 1.106(2) 0.037(6) Uiso 1 1 d . . . H6A H 0.7009(18) -0.1193(11) 1.1059(17) 0.014(5) Uiso 1 1 d . . . C7 C 0.61756(15) -0.15997(10) 0.62679(13) 0.0198(3) Uani 1 1 d . . . H7B H 0.5366(19) -0.1628(14) 0.6130(17) 0.024(5) Uiso 1 1 d . . . H7A H 0.6471(18) -0.2155(14) 0.6096(17) 0.024(5) Uiso 1 1 d . . . C8 C 0.55859(13) -0.00993(10) 0.73299(12) 0.0162(3) Uani 1 1 d . . . H8 H 0.5178(16) -0.0272(12) 0.6610(15) 0.014(5) Uiso 1 1 d . . . C9 C 0.46174(14) 0.11573(10) 0.69245(13) 0.0179(3) Uani 1 1 d . . . H9B H 0.4147(17) 0.0816(12) 0.6381(16) 0.015(5) Uiso 1 1 d . . . H9A H 0.4109(17) 0.1420(12) 0.7335(16) 0.014(5) Uiso 1 1 d . . . C10 C 0.52570(15) 0.17858(10) 0.63624(13) 0.0200(3) Uani 1 1 d . . . H10B H 0.465(2) 0.2100(15) 0.583(2) 0.034(6) Uiso 1 1 d . . . H10A H 0.5752(19) 0.1487(15) 0.5959(18) 0.026(5) Uiso 1 1 d . . . C11 C 0.59002(13) 0.24170(10) 0.70772(12) 0.0171(3) Uani 1 1 d . . . C12 C 0.67009(14) 0.36235(10) 0.75310(13) 0.0192(3) Uani 1 1 d . . . C13 C 0.71202(16) 0.44314(11) 0.75750(16) 0.0251(4) Uani 1 1 d . . . H13 H 0.700(2) 0.4774(15) 0.6992(19) 0.032(6) Uiso 1 1 d . . . C14 C 0.76552(16) 0.47087(11) 0.85589(17) 0.0271(4) Uani 1 1 d . . . H14 H 0.798(2) 0.5266(16) 0.8659(19) 0.037(6) Uiso 1 1 d . . . C15 C 0.77508(16) 0.42034(11) 0.94598(16) 0.0259(4) Uani 1 1 d . . . H15 H 0.8121(19) 0.4436(14) 1.0111(18) 0.026(6) Uiso 1 1 d . . . C16 C 0.73537(15) 0.33928(11) 0.94125(14) 0.0209(3) Uani 1 1 d . . . H16 H 0.7445(18) 0.3072(13) 1.0012(18) 0.022(5) Uiso 1 1 d . . . C17 C 0.68321(13) 0.30979(10) 0.84193(12) 0.0165(3) Uani 1 1 d . . . C18 C 0.93376(17) 0.17028(15) 1.12830(16) 0.0300(4) Uani 1 1 d . . . H18C H 0.901(2) 0.1452(16) 1.183(2) 0.037(6) Uiso 1 1 d . . . H18B H 1.010(2) 0.1575(17) 1.138(2) 0.042(7) Uiso 1 1 d . . . H18A H 0.926(2) 0.2285(19) 1.133(2) 0.052(8) Uiso 1 1 d . . . C19 C 0.86838(14) 0.14069(11) 1.02345(13) 0.0201(3) Uani 1 1 d . . . C20 C 0.92432(16) 0.10042(13) 0.95143(15) 0.0277(4) Uani 1 1 d . . . H20 H 1.010(2) 0.0854(16) 0.972(2) 0.038(7) Uiso 1 1 d . . . C21 C 0.87248(14) 0.08085(11) 0.84701(14) 0.0228(3) Uani 1 1 d . . . C22 C 0.94261(18) 0.04419(17) 0.77072(18) 0.0404(5) Uani 1 1 d . . . H22A H 0.8983 0.0034 0.7272 0.061 Uiso 1 1 calc R . . H22B H 1.0096 0.0186 0.8099 0.061 Uiso 1 1 calc R . . H22C H 0.9646 0.0872 0.7265 0.061 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 V1 0.01549(14) 0.01407(14) 0.01017(13) -0.00027(8) 0.00177(9) 0.00027(9) O1 0.0195(5) 0.0192(5) 0.0135(5) -0.0006(4) 0.0028(4) 0.0017(4) N1 0.0186(6) 0.0163(6) 0.0173(6) 0.0005(5) 0.0028(5) -0.0002(5) C1 0.0163(6) 0.0147(7) 0.0146(7) 0.0002(5) 0.0031(5) -0.0008(5) O1W 0.0304(7) 0.0213(7) 0.0399(8) 0.0079(6) 0.0077(6) 0.0044(5) C1W 0.0330(12) 0.0612(18) 0.117(3) 0.0521(19) -0.0197(15) -0.0019(12) O2 0.0228(6) 0.0150(5) 0.0124(5) -0.0006(4) 0.0018(4) 0.0016(4) N2 0.0167(6) 0.0160(6) 0.0137(6) 0.0012(5) 0.0020(5) 0.0001(5) C2 0.0153(6) 0.0161(7) 0.0157(7) 0.0009(5) 0.0009(5) -0.0019(5) O3 0.0180(5) 0.0219(6) 0.0157(5) -0.0016(4) 0.0041(4) -0.0001(4) N3 0.0271(7) 0.0180(7) 0.0152(6) 0.0033(5) 0.0061(5) 0.0008(5) C3 0.0191(7) 0.0150(7) 0.0194(7) -0.0030(6) 0.0036(6) -0.0012(5) O4 0.0190(5) 0.0188(6) 0.0142(5) -0.0011(4) 0.0010(4) -0.0010(4) N4 0.0196(6) 0.0156(6) 0.0125(6) -0.0006(5) 0.0025(5) -0.0005(5) C4 0.0178(7) 0.0148(7) 0.0159(7) -0.0015(5) 0.0027(5) -0.0029(5) C5 0.0160(6) 0.0152(7) 0.0154(7) -0.0006(5) 0.0015(5) -0.0016(5) O5 0.0273(6) 0.0225(6) 0.0170(6) 0.0014(5) 0.0047(5) 0.0012(5) C6 0.0229(8) 0.0182(8) 0.0149(7) 0.0013(6) 0.0015(6) 0.0024(6) C7 0.0242(8) 0.0188(8) 0.0156(7) -0.0034(6) 0.0009(6) -0.0023(6) C8 0.0171(7) 0.0186(7) 0.0124(7) -0.0008(5) 0.0017(5) -0.0024(5) C9 0.0178(7) 0.0184(7) 0.0160(7) 0.0008(6) -0.0013(6) 0.0012(6) C10 0.0276(8) 0.0193(7) 0.0124(7) 0.0005(6) 0.0016(6) 0.0004(6) C11 0.0205(7) 0.0178(7) 0.0137(7) 0.0014(5) 0.0050(6) 0.0022(6) C12 0.0207(7) 0.0182(7) 0.0202(8) 0.0013(6) 0.0080(6) 0.0012(6) C13 0.0273(8) 0.0177(8) 0.0325(9) 0.0047(7) 0.0111(7) 0.0009(6) C14 0.0255(8) 0.0146(8) 0.0419(11) -0.0025(7) 0.0080(8) -0.0008(6) C15 0.0248(8) 0.0199(8) 0.0319(9) -0.0068(7) 0.0012(7) -0.0003(6) C16 0.0227(8) 0.0193(8) 0.0202(8) -0.0030(6) 0.0023(6) 0.0015(6) C17 0.0184(7) 0.0147(7) 0.0172(7) -0.0007(5) 0.0055(6) 0.0003(5) C18 0.0238(9) 0.0437(12) 0.0201(9) -0.0046(8) -0.0034(7) -0.0048(8) C19 0.0193(7) 0.0231(8) 0.0169(7) 0.0013(6) 0.0000(6) -0.0040(6) C20 0.0182(8) 0.0403(10) 0.0237(9) -0.0027(8) 0.0007(7) 0.0030(7) C21 0.0202(7) 0.0261(9) 0.0227(8) -0.0025(7) 0.0052(6) 0.0005(6) C22 0.0250(9) 0.0637(15) 0.0331(11) -0.0171(10) 0.0063(8) 0.0077(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 V1 O1 1.6204(12) . ? V1 O2 1.9647(11) . ? V1 O4 1.9841(11) . ? V1 N2 2.0743(13) . ? V1 N4 2.1362(13) . ? V1 O3 2.1484(12) . ? N1 C2 1.328(2) . ? N1 C3 1.362(2) . ? C1 O2 1.3036(18) . ? C1 C5 1.416(2) . ? C1 C2 1.430(2) . ? O1W C1W 1.391(3) . ? O1W H1O 0.79(3) . ? C1W H1W1 0.9600 . ? C1W H1W2 0.9600 . ? C1W H1W3 0.9600 . ? N2 C8 1.284(2) . ? N2 C9 1.468(2) . ? C2 C6 1.496(2) . ? O3 C21 1.259(2) . ? N3 C11 1.345(2) . ? N3 C12 1.373(2) . ? N3 H3N 0.82(3) . ? C3 C4 1.374(2) . ? C3 H3 0.93(2) . ? O4 C19 1.279(2) . ? N4 C11 1.332(2) . ? N4 C17 1.406(2) . ? C4 C5 1.413(2) . ? C4 C7 1.510(2) . ? C5 C8 1.453(2) . ? O5 C7 1.425(2) . ? O5 H5 0.81(3) . ? C6 H6C 0.97(3) . ? C6 H6B 0.96(3) . ? C6 H6A 0.91(2) . ? C7 H7B 0.95(2) . ? C7 H7A 1.00(2) . ? C8 H8 1.005(19) . ? C9 C10 1.521(2) . ? C9 H9B 0.98(2) . ? C9 H9A 0.97(2) . ? C10 C11 1.491(2) . ? C10 H10B 1.04(2) . ? C10 H10A 0.98(2) . ? C12 C13 1.395(2) . ? C12 C17 1.405(2) . ? C13 C14 1.384(3) . ? C13 H13 0.92(2) . ? C14 C15 1.400(3) . ? C14 H14 0.98(3) . ? C15 C16 1.390(3) . ? C15 H15 0.95(2) . ? C16 C17 1.399(2) . ? C16 H16 0.92(2) . ? C18 C19 1.509(2) . ? C18 H18C 0.95(3) . ? C18 H18B 0.92(3) . ? C18 H18A 0.95(3) . ? C19 C20 1.388(3) . ? C20 C21 1.408(3) . ? C20 H20 1.04(3) . ? C21 C22 1.510(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 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 O1 V1 O2 100.58(5) . . ? O1 V1 O4 98.48(5) . . ? O2 V1 O4 87.15(5) . . ? O1 V1 N2 98.87(6) . . ? O2 V1 N2 86.78(5) . . ? O4 V1 N2 162.40(5) . . ? O1 V1 N4 93.26(6) . . ? O2 V1 N4 166.02(5) . . ? O4 V1 N4 92.83(5) . . ? N2 V1 N4 89.13(5) . . ? O1 V1 O3 173.95(5) . . ? O2 V1 O3 85.22(5) . . ? O4 V1 O3 83.42(5) . . ? N2 V1 O3 79.61(5) . . ? N4 V1 O3 80.89(5) . . ? C2 N1 C3 118.80(14) . . ? O2 C1 C5 124.81(14) . . ? O2 C1 C2 117.95(13) . . ? C5 C1 C2 117.23(14) . . ? C1W O1W H1O 109(2) . . ? O1W C1W H1W1 109.5 . . ? O1W C1W H1W2 109.5 . . ? H1W1 C1W H1W2 109.5 . . ? O1W C1W H1W3 109.5 . . ? H1W1 C1W H1W3 109.5 . . ? H1W2 C1W H1W3 109.5 . . ? C1 O2 V1 126.89(10) . . ? C8 N2 C9 116.93(13) . . ? C8 N2 V1 125.02(11) . . ? C9 N2 V1 117.66(10) . . ? N1 C2 C1 122.64(14) . . ? N1 C2 C6 118.84(14) . . ? C1 C2 C6 118.52(14) . . ? C21 O3 V1 127.26(11) . . ? C11 N3 C12 108.30(14) . . ? C11 N3 H3N 124(2) . . ? C12 N3 H3N 128(2) . . ? N1 C3 C4 123.46(15) . . ? N1 C3 H3 116.6(14) . . ? C4 C3 H3 120.0(14) . . ? C19 O4 V1 131.33(11) . . ? C11 N4 C17 105.26(13) . . ? C11 N4 V1 124.90(11) . . ? C17 N4 V1 129.55(10) . . ? C3 C4 C5 118.39(14) . . ? C3 C4 C7 120.13(14) . . ? C5 C4 C7 121.49(14) . . ? C4 C5 C1 119.11(14) . . ? C4 C5 C8 119.57(14) . . ? C1 C5 C8 121.19(14) . . ? C7 O5 H5 112.6(17) . . ? C2 C6 H6C 108.6(15) . . ? C2 C6 H6B 111.0(15) . . ? H6C C6 H6B 114(2) . . ? C2 C6 H6A 107.8(13) . . ? H6C C6 H6A 106.6(19) . . ? H6B C6 H6A 108(2) . . ? O5 C7 C4 112.72(13) . . ? O5 C7 H7B 107.3(13) . . ? C4 C7 H7B 109.6(13) . . ? O5 C7 H7A 112.4(12) . . ? C4 C7 H7A 107.1(12) . . ? H7B C7 H7A 107.5(18) . . ? N2 C8 C5 125.13(14) . . ? N2 C8 H8 117.8(11) . . ? C5 C8 H8 117.0(11) . . ? N2 C9 C10 110.16(13) . . ? N2 C9 H9B 110.8(11) . . ? C10 C9 H9B 108.1(12) . . ? N2 C9 H9A 108.5(12) . . ? C10 C9 H9A 112.0(12) . . ? H9B C9 H9A 107.2(16) . . ? C11 C10 C9 114.38(13) . . ? C11 C10 H10B 107.2(14) . . ? C9 C10 H10B 106.8(14) . . ? C11 C10 H10A 111.6(14) . . ? C9 C10 H10A 108.5(14) . . ? H10B C10 H10A 108.1(19) . . ? N4 C11 N3 112.23(14) . . ? N4 C11 C10 127.06(15) . . ? N3 C11 C10 120.70(14) . . ? N3 C12 C13 131.44(16) . . ? N3 C12 C17 105.68(14) . . ? C13 C12 C17 122.88(16) . . ? C14 C13 C12 116.44(17) . . ? C14 C13 H13 121.6(15) . . ? C12 C13 H13 121.8(15) . . ? C13 C14 C15 121.30(16) . . ? C13 C14 H14 121.7(15) . . ? C15 C14 H14 117.0(15) . . ? C16 C15 C14 122.26(17) . . ? C16 C15 H15 120.9(14) . . ? C14 C15 H15 116.8(14) . . ? C15 C16 C17 117.09(16) . . ? C15 C16 H16 120.4(14) . . ? C17 C16 H16 122.5(14) . . ? C16 C17 C12 119.95(15) . . ? C16 C17 N4 131.48(15) . . ? C12 C17 N4 108.50(14) . . ? C19 C18 H18C 107.9(16) . . ? C19 C18 H18B 113.4(17) . . ? H18C C18 H18B 109(2) . . ? C19 C18 H18A 109.1(18) . . ? H18C C18 H18A 109(2) . . ? H18B C18 H18A 109(2) . . ? O4 C19 C20 125.11(16) . . ? O4 C19 C18 114.55(16) . . ? C20 C19 C18 120.32(16) . . ? C19 C20 C21 123.50(16) . . ? C19 C20 H20 120.0(14) . . ? C21 C20 H20 116.5(14) . . ? O3 C21 C20 124.24(16) . . ? O3 C21 C22 115.80(16) . . ? C20 C21 C22 119.95(16) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C5 C1 O2 V1 -22.1(2) . . . . ? C2 C1 O2 V1 159.18(11) . . . . ? O1 V1 O2 C1 131.28(13) . . . . ? O4 V1 O2 C1 -130.61(13) . . . . ? N2 V1 O2 C1 32.85(13) . . . . ? N4 V1 O2 C1 -40.3(3) . . . . ? O3 V1 O2 C1 -46.98(12) . . . . ? O1 V1 N2 C8 -126.30(13) . . . . ? O2 V1 N2 C8 -26.09(13) . . . . ? O4 V1 N2 C8 43.9(2) . . . . ? N4 V1 N2 C8 140.54(13) . . . . ? O3 V1 N2 C8 59.64(13) . . . . ? O1 V1 N2 C9 61.07(12) . . . . ? O2 V1 N2 C9 161.28(11) . . . . ? O4 V1 N2 C9 -128.73(16) . . . . ? N4 V1 N2 C9 -32.10(11) . . . . ? O3 V1 N2 C9 -112.99(11) . . . . ? C3 N1 C2 C1 -1.9(2) . . . . ? C3 N1 C2 C6 177.91(14) . . . . ? O2 C1 C2 N1 -174.78(14) . . . . ? C5 C1 C2 N1 6.4(2) . . . . ? O2 C1 C2 C6 5.4(2) . . . . ? C5 C1 C2 C6 -173.45(14) . . . . ? O2 V1 O3 C21 -64.92(14) . . . . ? O4 V1 O3 C21 22.75(14) . . . . ? N2 V1 O3 C21 -152.51(15) . . . . ? N4 V1 O3 C21 116.70(15) . . . . ? C2 N1 C3 C4 -3.5(2) . . . . ? O1 V1 O4 C19 164.48(14) . . . . ? O2 V1 O4 C19 64.20(14) . . . . ? N2 V1 O4 C19 -5.7(3) . . . . ? N4 V1 O4 C19 -101.80(14) . . . . ? O3 V1 O4 C19 -21.31(14) . . . . ? O1 V1 N4 C11 -103.48(13) . . . . ? O2 V1 N4 C11 68.3(3) . . . . ? O4 V1 N4 C11 157.85(13) . . . . ? N2 V1 N4 C11 -4.64(13) . . . . ? O3 V1 N4 C11 74.98(13) . . . . ? O1 V1 N4 C17 83.56(13) . . . . ? O2 V1 N4 C17 -104.7(2) . . . . ? O4 V1 N4 C17 -15.11(13) . . . . ? N2 V1 N4 C17 -177.60(13) . . . . ? O3 V1 N4 C17 -97.98(13) . . . . ? N1 C3 C4 C5 4.0(2) . . . . ? N1 C3 C4 C7 -176.09(15) . . . . ? C3 C4 C5 C1 0.8(2) . . . . ? C7 C4 C5 C1 -179.11(14) . . . . ? C3 C4 C5 C8 -175.04(14) . . . . ? C7 C4 C5 C8 5.0(2) . . . . ? O2 C1 C5 C4 175.63(14) . . . . ? C2 C1 C5 C4 -5.6(2) . . . . ? O2 C1 C5 C8 -8.6(2) . . . . ? C2 C1 C5 C8 170.15(14) . . . . ? C3 C4 C7 O5 -125.44(16) . . . . ? C5 C4 C7 O5 54.5(2) . . . . ? C9 N2 C8 C5 -178.68(14) . . . . ? V1 N2 C8 C5 8.6(2) . . . . ? C4 C5 C8 N2 -169.39(15) . . . . ? C1 C5 C8 N2 14.8(2) . . . . ? C8 N2 C9 C10 -104.28(16) . . . . ? V1 N2 C9 C10 68.96(15) . . . . ? N2 C9 C10 C11 -65.85(18) . . . . ? C17 N4 C11 N3 0.43(18) . . . . ? V1 N4 C11 N3 -173.95(11) . . . . ? C17 N4 C11 C10 -178.94(15) . . . . ? V1 N4 C11 C10 6.7(2) . . . . ? C12 N3 C11 N4 0.48(19) . . . . ? C12 N3 C11 C10 179.90(14) . . . . ? C9 C10 C11 N4 27.1(2) . . . . ? C9 C10 C11 N3 -152.21(15) . . . . ? C11 N3 C12 C13 179.76(18) . . . . ? C11 N3 C12 C17 -1.17(18) . . . . ? N3 C12 C13 C14 177.13(17) . . . . ? C17 C12 C13 C14 -1.8(3) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C13 C14 C15 C16 2.3(3) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C12 -1.7(2) . . . . ? C15 C16 C17 N4 -178.47(16) . . . . ? N3 C12 C17 C16 -175.97(15) . . . . ? C13 C12 C17 C16 3.2(2) . . . . ? N3 C12 C17 N4 1.44(17) . . . . ? C13 C12 C17 N4 -179.39(15) . . . . ? C11 N4 C17 C16 175.85(17) . . . . ? V1 N4 C17 C16 -10.1(3) . . . . ? C11 N4 C17 C12 -1.16(17) . . . . ? V1 N4 C17 C12 172.86(11) . . . . ? V1 O4 C19 C20 12.1(3) . . . . ? V1 O4 C19 C18 -169.53(13) . . . . ? O4 C19 C20 C21 7.0(3) . . . . ? C18 C19 C20 C21 -171.29(19) . . . . ? V1 O3 C21 C20 -15.3(3) . . . . ? V1 O3 C21 C22 166.25(14) . . . . ? C19 C20 C21 O3 -4.2(3) . . . . ? C19 C20 C21 C22 174.3(2) . . . . ? 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 O1W H1O N1 0.79(3) 1.98(3) 2.7589(19) 171(3) . N3 H3N O1 0.82(3) 2.01(3) 2.8205(18) 171(3) 4_565 O5 H5 O1W 0.81(3) 1.94(3) 2.731(2) 165(2) 4 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.162 _refine_diff_density_min -0.728 _refine_diff_density_rms 0.232