# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_C20H18N4O2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N4 O2' _chemical_formula_weight 346.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0659(7) _cell_length_b 15.2611(19) _cell_length_c 19.086(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.971(2) _cell_angle_gamma 90.00 _cell_volume 1745.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1044 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 17.53 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 13202 _diffrn_reflns_av_R_equivalents 0.1215 _diffrn_reflns_av_sigmaI/netI 0.1640 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3033 _reflns_number_gt 1116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0643P)^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 SHELXL _refine_ls_extinction_coef 0.0072(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3033 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1861 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1876 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 O2 O 0.4663(6) 0.3554(2) 0.4193(2) 0.0747(13) Uani 1 1 d . . . H2B H 0.4628 0.3498 0.3691 0.129 Uiso 1 1 d . . . H2A H 0.3187 0.3229 0.4331 0.126 Uiso 1 1 d . . . O1 O -0.6964(6) 0.1628(2) 0.73425(18) 0.0556(11) Uani 1 1 d . . . C3 C 0.0501(8) 0.1481(3) 0.4383(3) 0.0358(12) Uani 1 1 d . . . C4 C -0.1092(8) 0.1162(3) 0.4768(2) 0.0416(14) Uani 1 1 d . . . H4 H -0.1811 0.0623 0.4711 0.050 Uiso 1 1 calc R . . C5 C -0.1390(8) 0.1801(3) 0.5248(2) 0.0351(12) Uani 1 1 d . . . C6 C 0.0286(9) 0.3326(3) 0.5442(3) 0.0416(13) Uani 1 1 d . . . C7 C 0.2380(9) 0.3581(4) 0.5758(3) 0.0549(16) Uani 1 1 d . . . H7 H 0.3629 0.3228 0.5758 0.066 Uiso 1 1 calc R . . C8 C 0.2509(11) 0.4416(4) 0.6082(3) 0.0679(19) Uani 1 1 d . . . H8 H 0.3862 0.4625 0.6319 0.081 Uiso 1 1 calc R . . C9 C 0.0620(14) 0.4909(4) 0.6042(4) 0.080(2) Uani 1 1 d . . . H9 H 0.0684 0.5459 0.6252 0.096 Uiso 1 1 calc R . . C10 C -0.1360(12) 0.4600(4) 0.5696(3) 0.069(2) Uani 1 1 d . . . H10 H -0.2621 0.4953 0.5671 0.083 Uiso 1 1 calc R . . C11 C 0.1431(8) 0.1040(3) 0.3799(3) 0.0350(12) Uani 1 1 d . . . C12 C 0.3428(8) 0.1273(3) 0.3599(3) 0.0483(15) Uani 1 1 d . . . H12 H 0.4295 0.1718 0.3833 0.058 Uiso 1 1 calc R . . C13 C 0.4120(9) 0.0825(4) 0.3038(3) 0.0562(16) Uani 1 1 d . . . H13 H 0.5482 0.0960 0.2898 0.067 Uiso 1 1 calc R . . C14 C 0.2786(10) 0.0183(3) 0.2689(3) 0.0556(16) Uani 1 1 d . . . H14 H 0.3194 -0.0108 0.2302 0.067 Uiso 1 1 calc R . . C15 C 0.0825(10) -0.0013(4) 0.2934(3) 0.0569(16) Uani 1 1 d . . . H15 H -0.0064 -0.0457 0.2707 0.068 Uiso 1 1 calc R . . C16 C -0.2772(8) 0.1805(3) 0.5820(3) 0.0355(12) Uani 1 1 d . . . C17 C -0.2228(8) 0.2237(3) 0.6452(3) 0.0445(14) Uani 1 1 d . . . H17 H -0.0918 0.2563 0.6534 0.053 Uiso 1 1 calc R . . C18 C -0.3571(9) 0.2200(3) 0.6969(3) 0.0484(15) Uani 1 1 d . . . H18 H -0.3180 0.2508 0.7390 0.058 Uiso 1 1 calc R . . C19 C -0.5508(8) 0.1705(3) 0.6862(3) 0.0405(13) Uani 1 1 d . . . C20 C -0.6072(8) 0.1250(3) 0.6239(3) 0.0428(14) Uani 1 1 d . . . H20 H -0.7361 0.0911 0.6167 0.051 Uiso 1 1 calc R . . C21 C -0.4733(8) 0.1296(3) 0.5726(3) 0.0388(13) Uani 1 1 d . . . H21 H -0.5126 0.0986 0.5306 0.047 Uiso 1 1 calc R . . C22 C -0.6628(10) 0.2162(4) 0.7962(3) 0.0671(18) Uani 1 1 d . . . H22A H -0.5154 0.2065 0.8216 0.101 Uiso 1 1 calc R . . H22B H -0.7710 0.2013 0.8259 0.101 Uiso 1 1 calc R . . H22C H -0.6794 0.2767 0.7827 0.101 Uiso 1 1 calc R . . N1 N 0.0037(6) 0.2473(2) 0.5128(2) 0.0358(11) Uani 1 1 d . . . N2 N 0.1230(7) 0.2280(3) 0.4603(2) 0.0411(11) Uani 1 1 d . . . N1' N -0.1563(7) 0.3804(3) 0.5388(2) 0.0505(12) Uani 1 1 d . . . N1'' N 0.0112(7) 0.0401(3) 0.3485(2) 0.0480(12) 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 O2 0.079(3) 0.069(3) 0.083(3) 0.005(2) 0.034(2) -0.005(2) O1 0.062(3) 0.061(3) 0.048(2) -0.014(2) 0.021(2) -0.019(2) C3 0.037(3) 0.029(3) 0.042(3) 0.002(2) 0.007(3) -0.002(2) C4 0.041(3) 0.043(3) 0.042(3) -0.003(3) 0.009(3) 0.000(3) C5 0.035(3) 0.032(3) 0.040(3) 0.000(2) 0.012(3) -0.006(2) C6 0.037(3) 0.039(3) 0.051(4) 0.004(3) 0.014(3) -0.006(3) C7 0.057(4) 0.054(4) 0.054(4) -0.006(3) 0.011(3) -0.010(3) C8 0.070(5) 0.068(5) 0.070(5) -0.017(4) 0.025(4) -0.029(4) C9 0.108(6) 0.055(4) 0.089(5) -0.023(4) 0.056(5) -0.034(4) C10 0.095(6) 0.033(4) 0.091(5) 0.005(3) 0.049(5) 0.008(4) C11 0.030(3) 0.035(3) 0.038(3) 0.004(2) 0.001(3) 0.000(2) C12 0.039(3) 0.041(3) 0.065(4) -0.003(3) 0.010(3) -0.002(3) C13 0.044(4) 0.059(4) 0.070(4) -0.005(3) 0.023(3) 0.012(3) C14 0.072(5) 0.042(3) 0.055(4) 0.004(3) 0.018(4) 0.010(3) C15 0.062(4) 0.054(4) 0.056(4) -0.015(3) 0.014(4) -0.011(3) C16 0.032(3) 0.033(3) 0.041(3) 0.002(2) 0.003(3) 0.000(2) C17 0.040(3) 0.048(3) 0.044(4) -0.005(3) 0.003(3) -0.011(3) C18 0.054(4) 0.047(3) 0.045(4) -0.007(3) 0.009(3) -0.013(3) C19 0.038(3) 0.043(3) 0.043(4) -0.003(3) 0.013(3) -0.001(3) C20 0.035(3) 0.044(3) 0.049(3) -0.004(3) 0.003(3) -0.011(2) C21 0.040(3) 0.035(3) 0.042(3) -0.003(2) 0.006(3) -0.006(2) C22 0.090(5) 0.057(4) 0.058(4) -0.013(3) 0.023(4) -0.009(3) N1 0.039(3) 0.030(2) 0.038(3) -0.006(2) 0.008(2) -0.0044(19) N2 0.043(3) 0.040(3) 0.041(3) 0.000(2) 0.007(2) 0.003(2) N1' 0.053(3) 0.039(3) 0.064(3) 0.008(2) 0.021(3) -0.001(2) N1'' 0.043(3) 0.051(3) 0.050(3) -0.011(2) 0.010(2) -0.008(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 O2 H2B 0.9597 . ? O2 H2A 1.0908 . ? O1 C19 1.374(5) . ? O1 C22 1.424(5) . ? C3 N2 1.342(5) . ? C3 C4 1.390(6) . ? C3 C11 1.486(6) . ? C4 C5 1.370(6) . ? C4 H4 0.9300 . ? C5 N1 1.383(5) . ? C5 C16 1.477(6) . ? C6 N1' 1.328(6) . ? C6 C7 1.375(6) . ? C6 N1 1.431(6) . ? C7 C8 1.413(7) . ? C7 H7 0.9300 . ? C8 C9 1.363(8) . ? C8 H8 0.9300 . ? C9 C10 1.361(8) . ? C9 H9 0.9300 . ? C10 N1' 1.347(6) . ? C10 H10 0.9300 . ? C11 N1'' 1.342(6) . ? C11 C12 1.372(6) . ? C12 C13 1.389(6) . ? C12 H12 0.9300 . ? C13 C14 1.374(7) . ? C13 H13 0.9300 . ? C14 C15 1.377(7) . ? C14 H14 0.9300 . ? C15 N1'' 1.355(6) . ? C15 H15 0.9300 . ? C16 C17 1.368(6) . ? C16 C21 1.408(6) . ? C17 C18 1.375(6) . ? C17 H17 0.9300 . ? C18 C19 1.385(6) . ? C18 H18 0.9300 . ? C19 C20 1.372(6) . ? C20 C21 1.369(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N1 N2 1.356(5) . ? 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 H2B O2 H2A 108.0 . . ? C19 O1 C22 118.8(4) . . ? N2 C3 C4 112.0(4) . . ? N2 C3 C11 120.1(4) . . ? C4 C3 C11 127.9(4) . . ? C5 C4 C3 106.2(4) . . ? C5 C4 H4 126.9 . . ? C3 C4 H4 126.9 . . ? C4 C5 N1 105.5(4) . . ? C4 C5 C16 130.3(4) . . ? N1 C5 C16 124.1(4) . . ? N1' C6 C7 126.1(5) . . ? N1' C6 N1 115.8(5) . . ? C7 C6 N1 118.1(5) . . ? C6 C7 C8 115.6(5) . . ? C6 C7 H7 122.2 . . ? C8 C7 H7 122.2 . . ? C9 C8 C7 119.0(6) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 120.5(6) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N1' C10 C9 122.5(6) . . ? N1' C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N1'' C11 C12 123.6(5) . . ? N1'' C11 C3 113.2(4) . . ? C12 C11 C3 123.1(5) . . ? C11 C12 C13 118.3(5) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C14 C13 C12 119.8(5) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 117.8(5) . . ? C13 C14 H14 121.1 . . ? C15 C14 H14 121.1 . . ? N1'' C15 C14 124.0(5) . . ? N1'' C15 H15 118.0 . . ? C14 C15 H15 118.0 . . ? C17 C16 C21 117.4(5) . . ? C17 C16 C5 124.5(4) . . ? C21 C16 C5 118.0(4) . . ? C16 C17 C18 121.6(5) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C19 120.0(5) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? O1 C19 C20 115.8(4) . . ? O1 C19 C18 124.5(5) . . ? C20 C19 C18 119.7(5) . . ? C21 C20 C19 119.9(5) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C16 121.4(5) . . ? C20 C21 H21 119.3 . . ? C16 C21 H21 119.3 . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N2 N1 C5 112.4(4) . . ? N2 N1 C6 118.2(4) . . ? C5 N1 C6 129.3(4) . . ? C3 N2 N1 103.9(4) . . ? C6 N1' C10 116.3(5) . . ? C11 N1'' C15 116.5(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 N2 C3 C4 C5 0.8(5) . . . . ? C11 C3 C4 C5 179.6(5) . . . . ? C3 C4 C5 N1 0.0(5) . . . . ? C3 C4 C5 C16 -176.0(5) . . . . ? N1' C6 C7 C8 3.4(8) . . . . ? N1 C6 C7 C8 -177.7(4) . . . . ? C6 C7 C8 C9 -2.0(8) . . . . ? C7 C8 C9 C10 0.1(10) . . . . ? C8 C9 C10 N1' 0.8(10) . . . . ? N2 C3 C11 N1'' -159.9(4) . . . . ? C4 C3 C11 N1'' 21.3(7) . . . . ? N2 C3 C11 C12 19.3(7) . . . . ? C4 C3 C11 C12 -159.4(5) . . . . ? N1'' C11 C12 C13 0.3(7) . . . . ? C3 C11 C12 C13 -178.9(4) . . . . ? C11 C12 C13 C14 1.6(8) . . . . ? C12 C13 C14 C15 -2.4(8) . . . . ? C13 C14 C15 N1'' 1.5(8) . . . . ? C4 C5 C16 C17 147.0(5) . . . . ? N1 C5 C16 C17 -28.3(7) . . . . ? C4 C5 C16 C21 -29.7(7) . . . . ? N1 C5 C16 C21 154.9(4) . . . . ? C21 C16 C17 C18 -2.0(7) . . . . ? C5 C16 C17 C18 -178.7(5) . . . . ? C16 C17 C18 C19 1.2(8) . . . . ? C22 O1 C19 C20 -172.6(4) . . . . ? C22 O1 C19 C18 7.3(7) . . . . ? C17 C18 C19 O1 -179.7(5) . . . . ? C17 C18 C19 C20 0.2(8) . . . . ? O1 C19 C20 C21 179.2(4) . . . . ? C18 C19 C20 C21 -0.7(7) . . . . ? C19 C20 C21 C16 -0.1(7) . . . . ? C17 C16 C21 C20 1.4(7) . . . . ? C5 C16 C21 C20 178.4(4) . . . . ? C4 C5 N1 N2 -0.7(5) . . . . ? C16 C5 N1 N2 175.6(4) . . . . ? C4 C5 N1 C6 174.8(4) . . . . ? C16 C5 N1 C6 -8.9(8) . . . . ? N1' C6 N1 N2 120.0(5) . . . . ? C7 C6 N1 N2 -59.0(6) . . . . ? N1' C6 N1 C5 -55.2(7) . . . . ? C7 C6 N1 C5 125.7(5) . . . . ? C4 C3 N2 N1 -1.2(5) . . . . ? C11 C3 N2 N1 179.9(4) . . . . ? C5 N1 N2 C3 1.2(5) . . . . ? C6 N1 N2 C3 -174.9(4) . . . . ? C7 C6 N1' C10 -2.6(8) . . . . ? N1 C6 N1' C10 178.5(4) . . . . ? C9 C10 N1' C6 0.3(8) . . . . ? C12 C11 N1'' C15 -1.1(7) . . . . ? C3 C11 N1'' C15 178.1(4) . . . . ? C14 C15 N1'' C11 0.2(8) . . . . ? 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 O2 H2A N2 1.09 1.99 3.039(5) 159.8 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.290 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 948534' ####################################################################### # # 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_C20H16Cl2N4O1Zn1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl2 N4 O Zn' _chemical_formula_weight 464.64 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' Cl Cl 0.1484 0.1585 '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' Zn Zn 0.2839 1.4301 '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 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 13.105(3) _cell_length_b 21.483(5) _cell_length_c 8.0777(19) _cell_angle_alpha 90.00 _cell_angle_beta 103.413(4) _cell_angle_gamma 90.00 _cell_volume 2212.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1428 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 17.17 _exptl_crystal_description thin _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 16529 _diffrn_reflns_av_R_equivalents 0.1271 _diffrn_reflns_av_sigmaI/netI 0.2220 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3876 _reflns_number_gt 1322 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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 ; The paper reports that unspecified disordered solvent molecules were not modelled and the disordered density was taken into account using the SQUEEZE/PLATON procedure. 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^)+(0.0710P)^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_extinction_coef ? _refine_ls_number_reflns 3876 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1856 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_ref 0.2039 _refine_ls_wR_factor_gt 0.1895 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.000 _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 C5 C 0.3258(8) 0.2449(4) 0.1326(12) 0.039(3) Uani 1 1 d . . . C4 C 0.3984(8) 0.2896(4) 0.1971(13) 0.043(3) Uani 1 1 d . . . H4 H 0.3904 0.3324 0.1824 0.052 Uiso 1 1 calc R . . C3 C 0.4861(9) 0.2585(5) 0.2885(12) 0.047(3) Uani 1 1 d . . . C6 C 0.2185(8) 0.2469(5) 0.0133(12) 0.041(3) Uani 1 1 d . . . C7 C 0.1687(9) 0.3010(5) -0.0482(12) 0.050(3) Uani 1 1 d . . . H7 H 0.1989 0.3394 -0.0134 0.060 Uiso 1 1 calc R . . C8 C 0.0730(9) 0.2975(6) -0.1626(16) 0.066(3) Uani 1 1 d . . . H8 H 0.0371 0.3335 -0.2059 0.079 Uiso 1 1 calc R . . C9 C 0.0307(9) 0.2386(7) -0.2128(14) 0.073(4) Uani 1 1 d . . . H9 H -0.0322 0.2352 -0.2940 0.087 Uiso 1 1 calc R . . C10 C 0.0841(10) 0.1842(6) -0.1394(14) 0.068(4) Uani 1 1 d . . . H10 H 0.0545 0.1452 -0.1673 0.082 Uiso 1 1 calc R . . C11 C 0.5166(8) 0.1391(5) 0.3463(15) 0.045(3) Uani 1 1 d . . . C12 C 0.5927(8) 0.1361(5) 0.4852(13) 0.054(3) Uani 1 1 d . . . H12 H 0.6130 0.1718 0.5496 0.065 Uiso 1 1 calc R . . C13 C 0.6405(9) 0.0826(5) 0.5337(13) 0.063(3) Uani 1 1 d . . . H13 H 0.6943 0.0802 0.6316 0.075 Uiso 1 1 calc R . . C14 C 0.6082(10) 0.0298(5) 0.4343(16) 0.069(4) Uani 1 1 d . . . H14 H 0.6403 -0.0085 0.4638 0.083 Uiso 1 1 calc R . . C15 C 0.5282(9) 0.0357(5) 0.2925(15) 0.057(3) Uani 1 1 d . . . H15 H 0.5088 0.0010 0.2238 0.068 Uiso 1 1 calc R . . C16 C 0.5893(8) 0.2851(4) 0.3704(12) 0.046(3) Uani 1 1 d . . . C17 C 0.5910(9) 0.3429(4) 0.4485(12) 0.051(3) Uani 1 1 d . . . H17 H 0.5278 0.3610 0.4564 0.062 Uiso 1 1 calc R . . C18 C 0.6831(9) 0.3741(5) 0.5144(12) 0.051(3) Uani 1 1 d . . . H18 H 0.6833 0.4125 0.5678 0.061 Uiso 1 1 calc R . . C19 C 0.7760(9) 0.3460(6) 0.4979(13) 0.055(3) Uani 1 1 d . . . C20 C 0.7740(10) 0.2882(5) 0.4219(13) 0.064(3) Uani 1 1 d . . . H20 H 0.8368 0.2687 0.4175 0.076 Uiso 1 1 calc R . . C21 C 0.6801(8) 0.2589(5) 0.3525(13) 0.057(3) Uani 1 1 d . . . H21 H 0.6791 0.2215 0.2940 0.069 Uiso 1 1 calc R . . C22 C 0.8766(10) 0.4352(5) 0.628(2) 0.143(7) Uani 1 1 d . . . H22A H 0.8242 0.4600 0.5538 0.214 Uiso 1 1 calc R . . H22B H 0.9446 0.4528 0.6333 0.214 Uiso 1 1 calc R . . H22C H 0.8632 0.4347 0.7398 0.214 Uiso 1 1 calc R . . Cl1 Cl 0.2047(2) 0.05568(12) 0.2420(4) 0.0687(9) Uani 1 1 d . . . Cl2 Cl 0.3069(2) 0.06673(13) -0.1594(4) 0.0749(10) Uani 1 1 d . . . N1 N 0.4600(7) 0.1956(4) 0.2773(10) 0.042(2) Uani 1 1 d . . . N2 N 0.3598(7) 0.1874(3) 0.1749(10) 0.047(2) Uani 1 1 d . . . N1'' N 0.1775(7) 0.1896(4) -0.0298(11) 0.052(2) Uani 1 1 d . . . N1' N 0.4765(7) 0.0890(4) 0.2478(10) 0.055(2) Uani 1 1 d . . . O1 O 0.8731(6) 0.3702(4) 0.5607(11) 0.089(3) Uani 1 1 d . . . Zn1 Zn 0.28522(10) 0.10986(5) 0.07830(15) 0.0575(5) 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 C5 0.047(7) 0.032(6) 0.045(7) 0.010(5) 0.024(6) 0.005(6) C4 0.047(7) 0.025(6) 0.064(7) -0.003(5) 0.026(6) 0.009(6) C3 0.060(8) 0.057(7) 0.026(6) -0.005(5) 0.013(6) -0.006(7) C6 0.038(7) 0.053(7) 0.030(6) 0.011(6) 0.007(5) 0.004(6) C7 0.056(8) 0.047(7) 0.048(7) 0.027(6) 0.015(6) 0.018(6) C8 0.035(8) 0.080(10) 0.083(10) 0.031(8) 0.015(7) 0.016(7) C9 0.043(8) 0.119(12) 0.050(8) 0.041(9) -0.002(6) 0.024(9) C10 0.043(8) 0.116(11) 0.043(8) 0.017(8) 0.003(7) -0.004(8) C11 0.048(7) 0.040(7) 0.049(7) 0.006(6) 0.017(6) 0.013(6) C12 0.060(8) 0.081(9) 0.018(6) 0.004(6) 0.003(6) 0.013(7) C13 0.101(10) 0.047(7) 0.037(7) 0.017(6) 0.011(7) 0.040(7) C14 0.077(10) 0.059(8) 0.073(9) 0.019(7) 0.020(8) 0.044(7) C15 0.061(8) 0.028(6) 0.076(9) -0.001(6) 0.005(7) 0.010(6) C16 0.044(7) 0.042(6) 0.048(7) -0.007(5) 0.003(6) 0.006(6) C17 0.065(8) 0.040(6) 0.051(7) -0.002(6) 0.016(6) 0.002(6) C18 0.052(8) 0.048(7) 0.048(7) -0.007(5) 0.000(6) 0.000(6) C19 0.031(7) 0.076(9) 0.048(7) 0.008(7) -0.012(6) -0.007(7) C20 0.083(10) 0.052(8) 0.065(8) 0.021(7) 0.037(8) 0.013(7) C21 0.043(7) 0.068(8) 0.067(8) 0.008(6) 0.026(6) -0.002(7) C22 0.080(10) 0.036(8) 0.28(2) -0.008(10) -0.032(12) -0.019(7) Cl1 0.074(2) 0.0623(19) 0.076(2) 0.0111(16) 0.0296(17) -0.0025(16) Cl2 0.099(2) 0.0651(19) 0.069(2) -0.0128(16) 0.0379(19) -0.0089(18) N1 0.046(6) 0.037(5) 0.046(6) -0.006(4) 0.015(5) -0.002(5) N2 0.052(6) 0.039(5) 0.049(6) 0.001(4) 0.011(5) 0.009(5) N1'' 0.055(7) 0.058(6) 0.045(6) -0.008(5) 0.016(5) -0.006(5) N1' 0.077(7) 0.033(5) 0.059(6) 0.003(5) 0.024(5) 0.003(5) O1 0.062(6) 0.068(6) 0.129(7) -0.001(5) 0.006(5) 0.000(5) Zn1 0.0786(10) 0.0424(7) 0.0590(8) -0.0052(7) 0.0315(7) -0.0059(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 C5 N2 1.329(10) . ? C5 C4 1.368(12) . ? C5 C6 1.510(12) . ? C4 C3 1.385(12) . ? C4 H4 0.9300 . ? C3 N1 1.392(11) . ? C3 C16 1.476(13) . ? C6 N1'' 1.355(11) . ? C6 C7 1.369(12) . ? C7 C8 1.376(13) . ? C7 H7 0.9300 . ? C8 C9 1.403(15) . ? C8 H8 0.9300 . ? C9 C10 1.419(14) . ? C9 H9 0.9300 . ? C10 N1'' 1.339(12) . ? C10 H10 0.9300 . ? C11 C12 1.319(12) . ? C11 N1' 1.369(12) . ? C11 N1 1.463(12) . ? C12 C13 1.324(12) . ? C12 H12 0.9300 . ? C13 C14 1.397(14) . ? C13 H13 0.9300 . ? C14 C15 1.367(13) . ? C14 H14 0.9300 . ? C15 N1' 1.336(11) . ? C15 H15 0.9300 . ? C16 C21 1.354(12) . ? C16 C17 1.391(12) . ? C17 C18 1.375(12) . ? C17 H17 0.9300 . ? C18 C19 1.393(13) . ? C18 H18 0.9300 . ? C19 C20 1.385(13) . ? C19 O1 1.359(11) . ? C20 C21 1.380(13) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 O1 1.496(13) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? Cl1 Zn1 2.205(3) . ? Cl2 Zn1 2.209(3) . ? N1 N2 1.392(10) . ? N2 Zn1 1.997(8) . ? N1'' Zn1 2.263(9) . ? 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 N2 C5 C4 113.1(9) . . ? N2 C5 C6 113.5(9) . . ? C4 C5 C6 133.2(9) . . ? C3 C4 C5 106.4(9) . . ? C3 C4 H4 126.8 . . ? C5 C4 H4 126.8 . . ? N1 C3 C4 105.8(9) . . ? N1 C3 C16 126.2(10) . . ? C4 C3 C16 127.8(10) . . ? N1'' C6 C7 123.4(10) . . ? N1'' C6 C5 113.1(9) . . ? C7 C6 C5 123.5(10) . . ? C6 C7 C8 118.7(11) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C7 C8 C9 118.8(11) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C10 C9 C8 119.9(11) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N1'' C10 C9 119.4(12) . . ? N1'' C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 N1' 124.6(10) . . ? C12 C11 N1 125.6(11) . . ? N1' C11 N1 109.8(9) . . ? C13 C12 C11 120.5(11) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 118.3(11) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C13 C14 C15 118.6(10) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N1' C15 C14 123.2(10) . . ? N1' C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C21 C16 C17 119.9(10) . . ? C21 C16 C3 121.9(10) . . ? C17 C16 C3 117.7(9) . . ? C16 C17 C18 122.1(10) . . ? C16 C17 H17 119.0 . . ? C18 C17 H17 119.0 . . ? C17 C18 C19 117.4(10) . . ? C17 C18 H18 121.3 . . ? C19 C18 H18 121.3 . . ? C20 C19 O1 115.3(11) . . ? C20 C19 C18 120.3(11) . . ? O1 C19 C18 124.3(11) . . ? C19 C20 C21 120.8(11) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C16 C21 C20 119.4(11) . . ? C16 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 N1 N2 110.2(8) . . ? C3 N1 C11 133.3(10) . . ? N2 N1 C11 116.5(8) . . ? C5 N2 N1 104.5(8) . . ? C5 N2 Zn1 124.7(8) . . ? N1 N2 Zn1 130.3(6) . . ? C10 N1'' C6 119.7(10) . . ? C10 N1'' Zn1 125.6(8) . . ? C6 N1'' Zn1 114.4(7) . . ? C11 N1' C15 114.5(9) . . ? C19 O1 C22 116.1(9) . . ? N2 Zn1 Cl1 117.7(2) . . ? N2 Zn1 Cl2 122.7(2) . . ? Cl1 Zn1 Cl2 118.40(11) . . ? N2 Zn1 N1'' 74.0(3) . . ? Cl1 Zn1 N1'' 106.8(2) . . ? Cl2 Zn1 N1'' 100.2(2) . . ? 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 N2 C5 C4 C3 -0.1(11) . . . . ? C6 C5 C4 C3 -174.8(8) . . . . ? C5 C4 C3 N1 -1.4(10) . . . . ? C5 C4 C3 C16 174.2(8) . . . . ? N2 C5 C6 N1'' -0.7(10) . . . . ? C4 C5 C6 N1'' 174.0(9) . . . . ? N2 C5 C6 C7 -179.3(8) . . . . ? C4 C5 C6 C7 -4.6(15) . . . . ? N1'' C6 C7 C8 -1.4(14) . . . . ? C5 C6 C7 C8 177.0(8) . . . . ? C6 C7 C8 C9 -0.5(15) . . . . ? C7 C8 C9 C10 3.0(16) . . . . ? C8 C9 C10 N1'' -3.7(15) . . . . ? N1' C11 C12 C13 4.0(15) . . . . ? N1 C11 C12 C13 -178.3(9) . . . . ? C11 C12 C13 C14 0.0(16) . . . . ? C12 C13 C14 C15 -0.6(16) . . . . ? C13 C14 C15 N1' -2.7(16) . . . . ? N1 C3 C16 C21 41.4(14) . . . . ? C4 C3 C16 C21 -133.3(11) . . . . ? N1 C3 C16 C17 -147.1(9) . . . . ? C4 C3 C16 C17 38.1(13) . . . . ? C21 C16 C17 C18 -2.3(15) . . . . ? C3 C16 C17 C18 -173.9(9) . . . . ? C16 C17 C18 C19 1.0(14) . . . . ? C17 C18 C19 C20 -1.7(15) . . . . ? C17 C18 C19 O1 -178.0(9) . . . . ? O1 C19 C20 C21 -179.7(9) . . . . ? C18 C19 C20 C21 3.7(15) . . . . ? C17 C16 C21 C20 4.2(15) . . . . ? C3 C16 C21 C20 175.4(9) . . . . ? C19 C20 C21 C16 -4.9(15) . . . . ? C4 C3 N1 N2 2.5(10) . . . . ? C16 C3 N1 N2 -173.2(8) . . . . ? C4 C3 N1 C11 -179.3(8) . . . . ? C16 C3 N1 C11 5.0(15) . . . . ? C12 C11 N1 C3 26.2(15) . . . . ? N1' C11 N1 C3 -155.8(9) . . . . ? C12 C11 N1 N2 -155.7(9) . . . . ? N1' C11 N1 N2 22.4(10) . . . . ? C4 C5 N2 N1 1.7(10) . . . . ? C6 C5 N2 N1 177.4(6) . . . . ? C4 C5 N2 Zn1 -170.7(6) . . . . ? C6 C5 N2 Zn1 5.1(10) . . . . ? C3 N1 N2 C5 -2.6(9) . . . . ? C11 N1 N2 C5 178.9(7) . . . . ? C3 N1 N2 Zn1 169.2(6) . . . . ? C11 N1 N2 Zn1 -9.4(11) . . . . ? C9 C10 N1'' C6 1.8(13) . . . . ? C9 C10 N1'' Zn1 -172.3(7) . . . . ? C7 C6 N1'' C10 0.8(14) . . . . ? C5 C6 N1'' C10 -177.8(7) . . . . ? C7 C6 N1'' Zn1 175.5(7) . . . . ? C5 C6 N1'' Zn1 -3.0(9) . . . . ? C12 C11 N1' C15 -6.8(14) . . . . ? N1 C11 N1' C15 175.1(8) . . . . ? C14 C15 N1' C11 6.0(14) . . . . ? C20 C19 O1 C22 174.2(10) . . . . ? C18 C19 O1 C22 -9.3(16) . . . . ? C5 N2 Zn1 Cl1 -106.0(7) . . . . ? N1 N2 Zn1 Cl1 83.7(7) . . . . ? C5 N2 Zn1 Cl2 86.8(7) . . . . ? N1 N2 Zn1 Cl2 -83.5(7) . . . . ? C5 N2 Zn1 N1'' -5.1(7) . . . . ? N1 N2 Zn1 N1'' -175.4(8) . . . . ? C10 N1'' Zn1 N2 178.6(8) . . . . ? C6 N1'' Zn1 N2 4.2(6) . . . . ? C10 N1'' Zn1 Cl1 -66.7(7) . . . . ? C6 N1'' Zn1 Cl1 118.9(6) . . . . ? C10 N1'' Zn1 Cl2 57.3(7) . . . . ? C6 N1'' Zn1 Cl2 -117.1(6) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.000 150 40 ' ' 2 0.000 1.000 0.500 150 40 ' ' _platon_squeeze_details ; The final refinement show high values of residual non-modelled electronic density. Therefore, the Squeeze program was used to remove its contribution to the overal intensity data. An improvement was observed in all refinement parameters and residual when this procedure is applied. ; _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.613 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 948535' ####################################################################### # # 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_C21H16Cl4N4O1Pd1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 Cl4 N4 O Pd' _chemical_formula_weight 588.58 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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.6930(11) _cell_length_b 13.8330(11) _cell_length_c 28.947(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.969(3) _cell_angle_gamma 90.00 _cell_volume 4647.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3066 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.82 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 1.280 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 20530 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5082 _reflns_number_gt 2766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0670P)^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_extinction_coef ? _refine_ls_number_reflns 5082 _refine_ls_number_parameters 269 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.999 _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 Pd1 Pd 0.19330(4) 0.77970(3) 0.442113(16) 0.03877(17) Uani 1 1 d . . . Cl1 Cl 0.02441(14) 0.78393(12) 0.47437(6) 0.0562(5) Uani 1 1 d . . . N2 N 0.3445(4) 0.7950(3) 0.41404(16) 0.0377(12) Uani 1 1 d . . . O1 O 0.8700(4) 0.6535(5) 0.28992(17) 0.0834(17) Uani 1 1 d . . . Cl2 Cl 0.15483(14) 0.62273(12) 0.42152(6) 0.0545(4) Uani 1 1 d . . . N1 N 0.4166(4) 0.7408(3) 0.39120(17) 0.0411(12) Uani 1 1 d . . . N1'' N 0.2357(4) 0.9188(3) 0.46112(16) 0.0380(12) Uani 1 1 d . . . C5 C 0.5161(5) 0.7913(4) 0.3872(2) 0.0436(15) Uani 1 1 d . . . Cl3 Cl 0.1687(4) 0.4054(4) 0.21042(17) 0.223(2) Uiso 1 1 d D A . C4 C 0.5065(5) 0.8790(4) 0.4085(2) 0.0435(15) Uani 1 1 d . . . H4 H 0.5604 0.9286 0.4115 0.052 Uiso 1 1 calc R . . N1' N 0.3157(5) 0.6428(4) 0.33428(18) 0.0512(14) Uani 1 1 d . . . C3 C 0.4005(5) 0.8782(4) 0.4247(2) 0.0411(15) Uani 1 1 d . . . C6 C 0.3401(5) 0.9494(4) 0.45038(19) 0.0387(14) Uani 1 1 d . . . C7 C 0.3821(6) 1.0394(4) 0.4628(2) 0.0483(16) Uani 1 1 d . . . H7 H 0.4536 1.0589 0.4552 0.058 Uiso 1 1 calc R . . C8 C 0.3173(5) 1.1009(4) 0.4867(2) 0.0495(17) Uani 1 1 d . . . H8 H 0.3441 1.1626 0.4949 0.059 Uiso 1 1 calc R . . C9 C 0.2133(5) 1.0703(4) 0.4981(2) 0.0488(16) Uani 1 1 d . . . H9 H 0.1687 1.1102 0.5146 0.059 Uiso 1 1 calc R . . C10 C 0.1760(5) 0.9789(5) 0.4848(2) 0.0503(17) Uani 1 1 d . . . H10 H 0.1053 0.9581 0.4927 0.060 Uiso 1 1 calc R . . C11 C 0.3857(5) 0.6456(4) 0.3736(2) 0.0414(15) Uani 1 1 d . . . C12 C 0.4328(6) 0.5677(5) 0.3980(2) 0.0538(18) Uani 1 1 d . . . H12 H 0.4832 0.5753 0.4252 0.065 Uiso 1 1 calc R . . C13 C 0.4023(7) 0.4784(5) 0.3807(3) 0.067(2) Uani 1 1 d . . . H13 H 0.4325 0.4230 0.3958 0.081 Uiso 1 1 calc R . . C14 C 0.3267(7) 0.4711(5) 0.3408(3) 0.067(2) Uani 1 1 d . . . H14 H 0.3029 0.4109 0.3290 0.081 Uiso 1 1 calc R . . C15 C 0.2871(6) 0.5538(5) 0.3186(3) 0.063(2) Uani 1 1 d . . . H15 H 0.2374 0.5481 0.2911 0.076 Uiso 1 1 calc R . . C16 C 0.6084(5) 0.7521(4) 0.3629(2) 0.0429(16) Uani 1 1 d . . . C17 C 0.7179(6) 0.7430(5) 0.3852(2) 0.0505(17) Uani 1 1 d . . . H17 H 0.7322 0.7601 0.4164 0.061 Uiso 1 1 calc R . . C18 C 0.8095(6) 0.7086(5) 0.3625(2) 0.0531(18) Uani 1 1 d . . . H18 H 0.8830 0.7024 0.3786 0.064 Uiso 1 1 calc R . . C19 C 0.7893(6) 0.6846(5) 0.3168(2) 0.0520(17) Uani 1 1 d . . . C20 C 0.6801(6) 0.6934(6) 0.2932(3) 0.076(3) Uani 1 1 d . . . H20 H 0.6668 0.6768 0.2619 0.091 Uiso 1 1 calc R . . C21 C 0.5887(6) 0.7271(5) 0.3161(2) 0.066(2) Uani 1 1 d . . . H21 H 0.5152 0.7327 0.3001 0.079 Uiso 1 1 calc R . . C22 C 0.9841(7) 0.6353(9) 0.3141(3) 0.125(4) Uani 1 1 d . . . H22A H 1.0342 0.6140 0.2923 0.187 Uiso 1 1 calc R . . H22B H 0.9794 0.5861 0.3372 0.187 Uiso 1 1 calc R . . H22C H 1.0140 0.6936 0.3289 0.187 Uiso 1 1 calc R . . C23 C 0.2997(7) 0.3428(7) 0.2079(5) 0.206(7) Uiso 1 1 d D . . Cl4A Cl 0.3551(7) 0.4316(6) 0.1739(3) 0.232(3) Uiso 0.60 1 d PD A 1 Cl4B Cl 0.4335(9) 0.4003(9) 0.2229(4) 0.238(6) Uiso 0.40 1 d PD . 2 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 Pd1 0.0330(3) 0.0424(3) 0.0414(3) 0.0022(2) 0.0066(2) -0.0088(2) Cl1 0.0384(9) 0.0592(10) 0.0742(12) 0.0006(9) 0.0204(8) -0.0111(8) N2 0.040(3) 0.037(3) 0.037(3) 0.001(2) 0.007(2) -0.007(2) O1 0.050(3) 0.143(5) 0.058(3) -0.005(3) 0.010(3) 0.029(3) Cl2 0.0525(10) 0.0454(9) 0.0674(11) -0.0051(8) 0.0147(9) -0.0162(8) N1 0.036(3) 0.048(3) 0.041(3) -0.004(2) 0.011(2) -0.004(2) N1'' 0.036(3) 0.043(3) 0.037(3) -0.002(2) 0.011(2) -0.006(2) C5 0.041(4) 0.053(4) 0.039(4) -0.002(3) 0.011(3) -0.006(3) C4 0.040(4) 0.043(4) 0.050(4) -0.006(3) 0.015(3) -0.011(3) N1' 0.060(4) 0.048(3) 0.045(3) -0.003(3) 0.001(3) -0.009(3) C3 0.040(4) 0.042(3) 0.042(4) 0.002(3) 0.009(3) -0.009(3) C6 0.038(4) 0.042(3) 0.036(3) 0.002(3) 0.002(3) -0.010(3) C7 0.049(4) 0.045(4) 0.053(4) 0.004(3) 0.013(3) -0.013(3) C8 0.050(4) 0.039(3) 0.061(4) -0.005(3) 0.015(3) -0.007(3) C9 0.048(4) 0.043(4) 0.059(4) -0.008(3) 0.016(3) 0.001(3) C10 0.038(4) 0.056(4) 0.058(4) -0.007(3) 0.011(3) -0.008(3) C11 0.040(4) 0.039(3) 0.047(4) 0.000(3) 0.013(3) -0.004(3) C12 0.055(4) 0.060(5) 0.046(4) 0.011(4) 0.001(3) 0.007(4) C13 0.083(6) 0.041(4) 0.078(6) 0.010(4) 0.012(5) 0.003(4) C14 0.091(6) 0.046(4) 0.068(5) -0.012(4) 0.024(5) -0.008(4) C15 0.068(5) 0.059(5) 0.059(5) -0.021(4) -0.003(4) -0.007(4) C16 0.038(4) 0.049(4) 0.043(4) 0.000(3) 0.010(3) -0.004(3) C17 0.048(4) 0.059(4) 0.045(4) -0.003(3) 0.009(3) -0.013(3) C18 0.043(4) 0.066(5) 0.048(4) 0.002(4) -0.003(3) 0.004(3) C19 0.045(4) 0.070(5) 0.045(4) -0.003(3) 0.018(3) 0.008(3) C20 0.055(5) 0.130(8) 0.043(4) -0.018(4) 0.006(4) 0.015(5) C21 0.041(4) 0.104(6) 0.051(5) -0.014(4) 0.000(3) 0.011(4) C22 0.048(5) 0.251(14) 0.077(6) -0.013(7) 0.012(5) 0.056(7) _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 Pd1 N2 2.044(5) . ? Pd1 N1'' 2.046(5) . ? Pd1 Cl2 2.2819(17) . ? Pd1 Cl1 2.2853(16) . ? N2 C3 1.342(7) . ? N2 N1 1.358(6) . ? O1 C19 1.364(7) . ? O1 C22 1.451(8) . ? N1 C5 1.374(7) . ? N1 C11 1.443(7) . ? N1'' C10 1.327(7) . ? N1'' C6 1.363(7) . ? C5 C4 1.373(8) . ? C5 C16 1.461(8) . ? Cl3 C23 1.769(5) . ? C4 C3 1.376(8) . ? C4 H4 0.9300 . ? N1' C11 1.318(7) . ? N1' C15 1.340(8) . ? C3 C6 1.466(8) . ? C6 C7 1.370(8) . ? C7 C8 1.379(8) . ? C7 H7 0.9300 . ? C8 C9 1.366(8) . ? C8 H8 0.9300 . ? C9 C10 1.378(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.368(8) . ? C12 C13 1.365(9) . ? C12 H12 0.9300 . ? C13 C14 1.370(10) . ? C13 H13 0.9300 . ? C14 C15 1.365(10) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.367(8) . ? C16 C21 1.390(9) . ? C17 C18 1.406(9) . ? C17 H17 0.9300 . ? C18 C19 1.356(9) . ? C18 H18 0.9300 . ? C19 C20 1.380(9) . ? C20 C21 1.404(9) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 Cl4A 1.748(5) . ? C23 Cl4B 1.762(5) . ? Cl4B Cl4B 2.07(2) 2_655 ? 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 N2 Pd1 N1'' 79.42(18) . . ? N2 Pd1 Cl2 98.45(13) . . ? N1'' Pd1 Cl2 177.34(14) . . ? N2 Pd1 Cl1 172.58(13) . . ? N1'' Pd1 Cl1 93.41(13) . . ? Cl2 Pd1 Cl1 88.76(6) . . ? C3 N2 N1 105.7(5) . . ? C3 N2 Pd1 114.8(4) . . ? N1 N2 Pd1 139.0(4) . . ? C19 O1 C22 115.9(6) . . ? N2 N1 C5 110.1(5) . . ? N2 N1 C11 122.1(4) . . ? C5 N1 C11 127.7(5) . . ? C10 N1'' C6 117.7(5) . . ? C10 N1'' Pd1 127.0(4) . . ? C6 N1'' Pd1 115.2(4) . . ? C4 C5 N1 107.1(5) . . ? C4 C5 C16 130.6(6) . . ? N1 C5 C16 122.4(5) . . ? C5 C4 C3 105.8(5) . . ? C5 C4 H4 127.1 . . ? C3 C4 H4 127.1 . . ? C11 N1' C15 115.0(6) . . ? N2 C3 C4 111.3(5) . . ? N2 C3 C6 116.2(5) . . ? C4 C3 C6 132.5(5) . . ? N1'' C6 C7 121.6(6) . . ? N1'' C6 C3 114.0(5) . . ? C7 C6 C3 124.4(5) . . ? C6 C7 C8 119.4(6) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 119.3(6) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 118.5(6) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? N1'' C10 C9 123.4(6) . . ? N1'' C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N1' C11 C12 126.3(6) . . ? N1' C11 N1 115.8(5) . . ? C12 C11 N1 117.9(6) . . ? C13 C12 C11 116.9(6) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C12 C13 C14 119.3(7) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 118.8(7) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? N1' C15 C14 123.7(7) . . ? N1' C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C17 C16 C21 118.2(6) . . ? C17 C16 C5 120.8(6) . . ? C21 C16 C5 121.0(6) . . ? C16 C17 C18 122.3(6) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 119.1(6) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 O1 125.7(6) . . ? C18 C19 C20 120.2(6) . . ? O1 C19 C20 114.1(6) . . ? C19 C20 C21 120.5(6) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 119.8(6) . . ? C16 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? Cl4A C23 Cl4B 56.2(5) . . ? Cl4A C23 Cl3 93.5(5) . . ? Cl4B C23 Cl3 121.1(8) . . ? C23 Cl4B Cl4B 138.6(10) . 2_655 ? 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 N1'' Pd1 N2 C3 6.0(4) . . . . ? Cl2 Pd1 N2 C3 -172.3(4) . . . . ? Cl1 Pd1 N2 C3 21.2(13) . . . . ? N1'' Pd1 N2 N1 175.9(6) . . . . ? Cl2 Pd1 N2 N1 -2.5(6) . . . . ? Cl1 Pd1 N2 N1 -169.0(7) . . . . ? C3 N2 N1 C5 -0.9(6) . . . . ? Pd1 N2 N1 C5 -171.3(4) . . . . ? C3 N2 N1 C11 -179.3(5) . . . . ? Pd1 N2 N1 C11 10.3(9) . . . . ? N2 Pd1 N1'' C10 179.2(5) . . . . ? Cl2 Pd1 N1'' C10 -144(3) . . . . ? Cl1 Pd1 N1'' C10 1.2(5) . . . . ? N2 Pd1 N1'' C6 -5.0(4) . . . . ? Cl2 Pd1 N1'' C6 32(3) . . . . ? Cl1 Pd1 N1'' C6 177.0(4) . . . . ? N2 N1 C5 C4 0.7(7) . . . . ? C11 N1 C5 C4 179.0(6) . . . . ? N2 N1 C5 C16 -178.2(5) . . . . ? C11 N1 C5 C16 0.1(10) . . . . ? N1 C5 C4 C3 -0.2(7) . . . . ? C16 C5 C4 C3 178.6(6) . . . . ? N1 N2 C3 C4 0.8(7) . . . . ? Pd1 N2 C3 C4 173.9(4) . . . . ? N1 N2 C3 C6 -179.3(5) . . . . ? Pd1 N2 C3 C6 -6.2(7) . . . . ? C5 C4 C3 N2 -0.4(7) . . . . ? C5 C4 C3 C6 179.7(6) . . . . ? C10 N1'' C6 C7 -0.9(9) . . . . ? Pd1 N1'' C6 C7 -177.1(5) . . . . ? C10 N1'' C6 C3 179.4(5) . . . . ? Pd1 N1'' C6 C3 3.2(6) . . . . ? N2 C3 C6 N1'' 2.0(8) . . . . ? C4 C3 C6 N1'' -178.1(6) . . . . ? N2 C3 C6 C7 -177.7(6) . . . . ? C4 C3 C6 C7 2.2(11) . . . . ? N1'' C6 C7 C8 -0.2(9) . . . . ? C3 C6 C7 C8 179.5(6) . . . . ? C6 C7 C8 C9 1.1(10) . . . . ? C7 C8 C9 C10 -0.9(10) . . . . ? C6 N1'' C10 C9 1.1(9) . . . . ? Pd1 N1'' C10 C9 176.8(5) . . . . ? C8 C9 C10 N1'' -0.2(10) . . . . ? C15 N1' C11 C12 2.2(10) . . . . ? C15 N1' C11 N1 -179.4(5) . . . . ? N2 N1 C11 N1' 78.5(7) . . . . ? C5 N1 C11 N1' -99.6(7) . . . . ? N2 N1 C11 C12 -103.0(7) . . . . ? C5 N1 C11 C12 78.9(8) . . . . ? N1' C11 C12 C13 -1.7(10) . . . . ? N1 C11 C12 C13 180.0(6) . . . . ? C11 C12 C13 C14 -0.7(11) . . . . ? C12 C13 C14 C15 2.2(11) . . . . ? C11 N1' C15 C14 -0.5(10) . . . . ? C13 C14 C15 N1' -1.7(12) . . . . ? C4 C5 C16 C17 58.6(10) . . . . ? N1 C5 C16 C17 -122.8(7) . . . . ? C4 C5 C16 C21 -118.6(8) . . . . ? N1 C5 C16 C21 60.0(9) . . . . ? C21 C16 C17 C18 -0.6(10) . . . . ? C5 C16 C17 C18 -177.8(6) . . . . ? C16 C17 C18 C19 0.7(10) . . . . ? C17 C18 C19 O1 177.6(7) . . . . ? C17 C18 C19 C20 -0.4(11) . . . . ? C22 O1 C19 C18 7.0(12) . . . . ? C22 O1 C19 C20 -174.9(8) . . . . ? C18 C19 C20 C21 -0.1(12) . . . . ? O1 C19 C20 C21 -178.3(7) . . . . ? C17 C16 C21 C20 0.1(11) . . . . ? C5 C16 C21 C20 177.4(7) . . . . ? C19 C20 C21 C16 0.2(12) . . . . ? Cl4A C23 Cl4B Cl4B 177.5(15) . . . 2_655 ? Cl3 C23 Cl4B Cl4B 106.1(12) . . . 2_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.116 _refine_diff_density_min -1.015 _refine_diff_density_rms 0.109 #=======================================================================END _database_code_depnum_ccdc_archive 'CCDC 948536'