# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1558 data_shel93 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H17 Cl N4 O3 V' _chemical_formula_weight 435.76 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 '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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 17.07(2) _cell_length_b 9.82(1) _cell_length_c 11.51(1) _cell_angle_alpha 90.00 _cell_angle_beta 94.03(4) _cell_angle_gamma 90.00 _cell_volume 1925(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.5 _cell_measurement_theta_max 10.5 _exptl_crystal_description 'parallelipiped' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 1.48 _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'floating method' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 0.682 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Crystal Logic Dual Goniometer diffractometer' _diffrn_measurement_method 'theta-2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.9 _diffrn_reflns_number 2591 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 23.97 _reflns_number_total 2457 _reflns_number_observed 1544 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Program COLLECT (UCLA Crystallographic package, C.E.Strouse, 1994)' _computing_cell_refinement 'Program LEAST (UCLA Crystallographic package, C.E.Strouse, 1994)' _computing_data_reduction 'Program REDUCE (UCLA Crystallographic package, C.E.Strouse, 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 150 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+9.8064P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2307 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_obs 0.0663 _refine_ls_wR_factor_all 0.1923 _refine_ls_wR_factor_obs 0.1453 _refine_ls_goodness_of_fit_all 1.063 _refine_ls_goodness_of_fit_obs 1.126 _refine_ls_restrained_S_all 1.136 _refine_ls_restrained_S_obs 1.126 _refine_ls_shift/esd_max 0.217 _refine_ls_shift/esd_mean 0.011 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group V V 0.41988(8) 0.06412(14) 0.19893(12) 0.0452(4) Uani 1 d . . Cl Cl 0.47925(15) 0.2577(2) 0.3269(2) 0.0626(7) Uani 1 d . . O1 O 0.4033(3) -0.0547(5) 0.1020(4) 0.0410(12) Uani 1 d . . N1 N 0.5357(4) -0.0192(6) 0.2451(5) 0.044(2) Uani 1 d . . N2 N 0.4046(4) -0.0396(6) 0.3532(5) 0.043(2) Uani 1 d . . N3 N 0.3113(4) 0.1239(6) 0.2333(5) 0.044(2) Uani 1 d . . N4 N 0.4003(4) 0.2261(7) 0.0787(5) 0.045(2) Uani 1 d . . C1 C 0.6010(5) -0.0107(10) 0.1907(9) 0.052(2) Uani 1 d . . C2 C 0.6680(5) -0.0848(10) 0.2204(8) 0.058(2) Uani 1 d . . C3 C 0.6679(5) -0.1745(9) 0.3123(8) 0.054(2) Uani 1 d . . C4 C 0.6009(5) -0.1854(9) 0.3744(8) 0.053(2) Uani 1 d . . C5 C 0.5356(5) -0.1068(8) 0.3384(7) 0.045(2) Uani 1 d . . C6 C 0.4625(5) -0.1134(8) 0.3964(7) 0.047(2) Uani 1 d . . C7 C 0.3292(5) -0.0282(8) 0.3952(7) 0.046(2) Uani 1 d . . C8 C 0.3055(5) -0.0975(9) 0.4922(7) 0.048(2) Uani 1 d . . C9 C 0.2295(6) -0.0781(10) 0.5263(8) 0.057(2) Uani 1 d . . C10 C 0.1779(5) 0.0094(9) 0.4623(7) 0.052(2) Uani 1 d . . C11 C 0.2022(5) 0.0800(10) 0.3655(8) 0.051(2) Uani 1 d . . C12 C 0.2776(4) 0.0607(8) 0.3286(7) 0.045(2) Uani 1 d . . C13 C 0.2737(5) 0.2177(8) 0.1646(7) 0.047(2) Uani 1 d . . O2 O 0.2056(4) 0.2602(7) 0.1670(6) 0.073(2) Uani 1 d . . C14 C 0.3270(5) 0.2744(8) 0.0761(7) 0.048(2) Uani 1 d . . C15 C 0.3007(6) 0.3719(10) -0.0051(8) 0.058(3) Uani 1 d . . C16 C 0.3513(6) 0.4262(11) -0.0796(8) 0.066(3) Uani 1 d . . C17 C 0.4275(6) 0.3787(10) -0.0759(8) 0.062(3) Uani 1 d . . C18 C 0.4492(6) 0.2785(10) 0.0060(8) 0.061(3) Uani 1 d . . O3 O 0.0425(5) 0.0812(10) 0.6879(8) 0.110(3) Uani 1 d . . C19 C 0.1107(7) 0.0981(14) 0.7564(11) 0.104(4) Uani 1 d . . H19A H 0.1424(22) 0.1664(60) 0.7227(40) 0.135(29) Uiso 1 calc R . H19B H 0.1390(24) 0.0136(25) 0.7615(57) 0.135(29) Uiso 1 calc R . H19C H 0.0985(7) 0.1263(80) 0.8329(24) 0.135(29) Uiso 1 calc R . HO3 H 0.0318(91) -0.0257(178) 0.6362(146) 0.204 Uiso 1 d . . H1 H 0.6000(42) 0.0369(76) 0.1465(62) 0.024(25) Uiso 1 d . . H2 H 0.7116(46) -0.0778(81) 0.1782(67) 0.049(23) Uiso 1 d . . H3 H 0.7205(59) -0.2345(105) 0.3412(89) 0.102(35) Uiso 1 d . . H4 H 0.6028(49) -0.2278(90) 0.4382(76) 0.064(29) Uiso 1 d . . H6 H 0.4560(42) -0.1766(80) 0.4750(66) 0.054(22) Uiso 1 d . . H8 H 0.3380(44) -0.1520(81) 0.5396(69) 0.051(25) Uiso 1 d . . H9 H 0.2136(47) -0.1250(85) 0.5902(72) 0.058(26) Uiso 1 d . . H10 H 0.1214(68) 0.0248(118) 0.4912(100) 0.124(42) Uiso 1 d . . H11 H 0.1710(47) 0.1134(87) 0.3262(73) 0.049(29) Uiso 1 d . . H15 H 0.2579(55) 0.3948(102) -0.0005(86) 0.069(34) Uiso 1 d . . H16 H 0.3397(53) 0.5025(96) -0.1260(82) 0.076(30) Uiso 1 d . . H17 H 0.4594(49) 0.4117(91) -0.1237(77) 0.064(29) Uiso 1 d . . H18 H 0.4900(41) 0.2386(70) 0.0025(59) 0.025(20) Uiso 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 V 0.0494(8) 0.0462(9) 0.0393(8) 0.0070(7) -0.0019(6) 0.0032(7) Cl 0.085(2) 0.0486(13) 0.0515(13) -0.0016(10) -0.0151(11) -0.0051(12) O1 0.050(3) 0.043(3) 0.029(3) -0.007(2) -0.003(2) 0.002(3) N1 0.053(4) 0.043(4) 0.036(4) 0.003(3) -0.008(3) 0.004(3) N2 0.050(4) 0.043(4) 0.036(4) -0.001(3) -0.004(3) 0.000(3) N3 0.053(4) 0.043(4) 0.036(4) 0.012(3) 0.002(3) 0.006(3) N4 0.045(4) 0.049(4) 0.039(4) -0.006(3) -0.003(3) -0.005(3) C1 0.054(6) 0.051(6) 0.050(6) 0.010(5) 0.000(5) -0.002(5) C2 0.041(5) 0.070(7) 0.063(6) -0.009(5) -0.004(4) -0.002(5) C3 0.052(6) 0.056(6) 0.054(5) 0.009(5) -0.005(4) 0.008(4) C4 0.054(6) 0.055(6) 0.047(5) 0.016(5) -0.009(5) 0.007(4) C5 0.050(5) 0.042(5) 0.043(5) -0.001(4) -0.008(4) -0.005(4) C6 0.056(5) 0.041(5) 0.042(5) 0.010(4) -0.010(4) -0.007(4) C7 0.052(5) 0.044(5) 0.041(5) -0.010(4) 0.004(4) -0.009(4) C8 0.067(6) 0.049(5) 0.031(4) 0.003(4) 0.012(4) -0.014(5) C9 0.075(7) 0.058(6) 0.040(5) -0.002(5) 0.013(5) -0.019(5) C10 0.054(5) 0.061(6) 0.043(5) -0.011(4) 0.010(4) -0.011(5) C11 0.053(5) 0.050(6) 0.049(6) -0.013(5) -0.001(5) -0.004(5) C12 0.042(4) 0.049(5) 0.044(5) -0.002(4) 0.006(4) 0.000(4) C13 0.053(5) 0.049(5) 0.037(4) 0.000(4) -0.001(4) 0.002(4) O2 0.057(4) 0.080(5) 0.083(5) 0.021(4) 0.019(3) 0.030(4) C14 0.062(6) 0.038(5) 0.042(5) -0.003(4) -0.004(4) 0.007(4) C15 0.067(7) 0.064(6) 0.042(5) 0.008(5) -0.002(5) 0.016(6) C16 0.085(7) 0.065(7) 0.047(6) 0.023(5) -0.001(5) 0.007(6) C17 0.074(7) 0.069(7) 0.043(5) 0.018(5) 0.006(5) -0.007(5) C18 0.058(6) 0.062(7) 0.062(6) 0.010(5) 0.004(5) 0.011(5) O3 0.105(7) 0.101(7) 0.121(7) -0.006(6) 0.000(6) 0.017(5) C19 0.081(8) 0.124(12) 0.105(9) -0.010(9) 0.005(8) 0.014(8) _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 V O1 1.626(5) . ? V N3 2.010(7) . ? V N2 2.079(6) . ? V N4 2.120(7) . ? V N1 2.171(7) . ? V Cl 2.569(3) . ? N1 C1 1.319(11) . ? N1 C5 1.376(10) . ? N2 C6 1.296(10) . ? N2 C7 1.411(10) . ? N3 C13 1.346(10) . ? N3 C12 1.418(10) . ? N4 C18 1.326(11) . ? N4 C14 1.337(10) . ? C1 C2 1.377(13) . ? C2 C3 1.376(13) . ? C3 C4 1.395(12) . ? C4 C5 1.395(11) . ? C5 C6 1.458(11) . ? C7 C8 1.393(11) . ? C7 C12 1.425(11) . ? C8 C9 1.395(12) . ? C9 C10 1.402(13) . ? C10 C11 1.400(13) . ? C11 C12 1.396(11) . ? C13 O2 1.238(9) . ? C13 C14 1.519(11) . ? C14 C15 1.390(12) . ? C15 C16 1.368(14) . ? C16 C17 1.379(13) . ? C17 C18 1.395(13) . ? O3 C19 1.369(13) . ? 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 V N3 103.1(3) . . ? O1 V N2 102.0(3) . . ? N3 V N2 78.6(2) . . ? O1 V N4 94.5(3) . . ? N3 V N4 78.7(3) . . ? N2 V N4 154.4(3) . . ? O1 V N1 90.5(3) . . ? N3 V N1 154.0(2) . . ? N2 V N1 76.9(3) . . ? N4 V N1 122.8(3) . . ? O1 V Cl 165.3(2) . . ? N3 V Cl 90.2(2) . . ? N2 V Cl 86.6(2) . . ? N4 V Cl 81.8(2) . . ? N1 V Cl 79.8(2) . . ? C1 N1 C5 117.2(7) . . ? C1 N1 V 130.3(6) . . ? C5 N1 V 112.0(5) . . ? C6 N2 C7 127.0(7) . . ? C6 N2 V 117.6(5) . . ? C7 N2 V 115.2(5) . . ? C13 N3 C12 123.4(7) . . ? C13 N3 V 119.5(5) . . ? C12 N3 V 117.0(5) . . ? C18 N4 C14 118.6(8) . . ? C18 N4 V 128.7(6) . . ? C14 N4 V 112.6(5) . . ? N1 C1 C2 124.3(10) . . ? C3 C2 C1 118.9(9) . . ? C2 C3 C4 119.2(8) . . ? C5 C4 C3 118.2(8) . . ? N1 C5 C4 122.1(8) . . ? N1 C5 C6 115.7(7) . . ? C4 C5 C6 122.2(8) . . ? N2 C6 C5 116.9(7) . . ? C8 C7 N2 124.0(8) . . ? C8 C7 C12 121.8(8) . . ? N2 C7 C12 114.2(7) . . ? C7 C8 C9 119.2(9) . . ? C8 C9 C10 119.9(8) . . ? C11 C10 C9 120.7(9) . . ? C12 C11 C10 120.4(9) . . ? C11 C12 N3 127.5(8) . . ? C11 C12 C7 117.9(8) . . ? N3 C12 C7 114.5(6) . . ? O2 C13 N3 128.9(8) . . ? O2 C13 C14 119.9(7) . . ? N3 C13 C14 111.1(7) . . ? N4 C14 C15 121.1(9) . . ? N4 C14 C13 117.4(7) . . ? C15 C14 C13 121.5(8) . . ? C16 C15 C14 120.1(10) . . ? C15 C16 C17 119.0(9) . . ? C16 C17 C18 117.7(10) . . ? N4 C18 C17 123.4(10) . . ? _refine_diff_density_max 0.890 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.083