# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 loop_ _publ_author_name _publ_author_address G.Bruni 'Centro Grandi Strumenti, University of Pavia, Italy' M.Maietta ? V.Berbenni ? M.Bini '' S.Ferrari '' D.Capsoni '' M.BoiocchiC.Milanese '' A.Marini '' #TrackingRef '- monoclinic_new.cif' _publ_contact_author ; ?NAME? Dipartimento di Chimica Generale University of Pavia via Taramelli 12, I-27100 Pavia, ITALY ; _publ_contact_author_email giovanna.bruni@unipv.it _publ_section_title ; ? ; _publ_contact_author_name 'Bruni, Giovanna' data_1:1.5 _database_code_depnum_ccdc_archive 'CCDC 826306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 Cl N O2, 1.5(C10 H8 N2)' _chemical_formula_sum 'C30 H24 Cl N4 O2' _chemical_formula_weight 507.98 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' Cl Cl 0.1484 0.1585 '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 'P 21/c' _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 19.030(8) _cell_length_b 5.5550(15) _cell_length_c 25.191(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.33(3) _cell_angle_gamma 90.00 _cell_volume 2497.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4 _cell_measurement_theta_max 7 _exptl_crystal_description 'PLATY PRISM' _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9778 _exptl_absorpt_correction_T_max 0.9997 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 300 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2436 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.1307 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 20.05 _reflns_number_total 2341 _reflns_number_gt 1254 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'PROFIT (Streltsov & Zavodnik, 1989)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0928P)^2^+18.1751P] 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 2341 _refine_ls_number_parameters 335 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2039 _refine_ls_R_factor_gt 0.1322 _refine_ls_wR_factor_ref 0.3415 _refine_ls_wR_factor_gt 0.2950 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.006 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 Cl1 Cl -0.0598(2) 0.2896(8) 0.15011(19) 0.0970(16) Uani 1 1 d . . . C1 C 0.3066(10) 0.424(3) 0.1142(7) 0.087(5) Uani 1 1 d . . . H1 H 0.3291 0.3108 0.0981 0.104 Uiso 1 1 calc R . . C2 C 0.2347(10) 0.378(3) 0.1159(6) 0.076(5) Uani 1 1 d . . . H2 H 0.2072 0.2441 0.0981 0.091 Uiso 1 1 calc R . . C3 C 0.2067(9) 0.541(3) 0.1449(6) 0.069(4) Uani 1 1 d . . . C4 C 0.1368(9) 0.555(3) 0.1567(6) 0.067(4) Uani 1 1 d . . . C5 C 0.0767(9) 0.405(3) 0.1470(6) 0.067(4) Uani 1 1 d . . . H5 H 0.0738 0.2609 0.1274 0.081 Uiso 1 1 calc R . . C6 C 0.0212(8) 0.471(3) 0.1666(6) 0.076(5) Uani 1 1 d . . . C7 C 0.0239(8) 0.672(3) 0.1976(7) 0.079(5) Uani 1 1 d . . . H7 H -0.0151 0.7061 0.2106 0.095 Uiso 1 1 calc R . . C8 C 0.0850(10) 0.826(3) 0.2103(6) 0.088(5) Uani 1 1 d . . . H8 H 0.0881 0.9635 0.2322 0.105 Uiso 1 1 calc R . . C9 C 0.1422(9) 0.767(3) 0.1886(6) 0.064(4) Uani 1 1 d . . . C10 C 0.2464(9) 0.745(3) 0.1677(7) 0.078(5) Uani 1 1 d . . . C11 C 0.3162(9) 0.793(3) 0.1632(6) 0.070(4) Uani 1 1 d . . . H11 H 0.3430 0.9316 0.1786 0.084 Uiso 1 1 calc R . . C12 C 0.3434(9) 0.627(3) 0.1351(7) 0.072(4) Uani 1 1 d . . . C13 C 0.4236(9) 0.673(3) 0.1328(7) 0.093(6) Uani 1 1 d . . . H13 H 0.4291 0.5389 0.1093 0.112 Uiso 1 1 calc R . . C14 C 0.4823(9) 0.631(3) 0.1839(7) 0.110(6) Uani 1 1 d . . . H14A H 0.5286 0.6180 0.1768 0.165 Uiso 1 1 calc R . . H14B H 0.4731 0.4844 0.2005 0.165 Uiso 1 1 calc R . . H14C H 0.4855 0.7626 0.2094 0.165 Uiso 1 1 calc R . . C15 C 0.4260(10) 0.883(4) 0.0979(9) 0.091(6) Uani 1 1 d . . . N1 N 0.2082(6) 0.885(2) 0.1950(5) 0.069(3) Uani 1 1 d . . . H1N H 0.2232 1.0182 0.2125 0.083 Uiso 1 1 calc R . . O1 O 0.4654(8) 1.060(3) 0.1182(8) 0.158(7) Uani 1 1 d . . . O2 O 0.3848(8) 0.892(2) 0.0478(6) 0.131(5) Uani 1 1 d . . . H2O H 0.3836 1.0309 0.0363 0.158 Uiso 1 1 calc R . . C16 C 0.3128(13) 1.394(4) -0.0316(9) 0.124(8) Uani 1 1 d . . . H16 H 0.2802 1.3447 -0.0134 0.149 Uiso 1 1 calc R . . C17 C 0.2902(9) 1.576(4) -0.0692(8) 0.104(6) Uani 1 1 d . . . H17 H 0.2440 1.6480 -0.0753 0.125 Uiso 1 1 calc R . . C18 C 0.3331(8) 1.653(2) -0.0976(6) 0.064(4) Uani 1 1 d . . . C19 C 0.4005(9) 1.542(4) -0.0840(8) 0.114(7) Uani 1 1 d . . . H19 H 0.4338 1.5868 -0.1019 0.137 Uiso 1 1 calc R . . C20 C 0.4187(13) 1.372(4) -0.0459(10) 0.139(9) Uani 1 1 d . . . H20 H 0.4667 1.3081 -0.0370 0.166 Uiso 1 1 calc R . . C21 C 0.2277(10) 2.167(4) -0.1865(8) 0.105(6) Uani 1 1 d U . . H21 H 0.1868 2.2604 -0.1874 0.126 Uiso 1 1 calc R . . C22 C 0.2470(11) 1.988(3) -0.1461(8) 0.115(7) Uani 1 1 d . . . H22 H 0.2201 1.9635 -0.1220 0.138 Uiso 1 1 calc R . . C23 C 0.3075(9) 1.850(3) -0.1431(7) 0.073(4) Uani 1 1 d . . . C24 C 0.3470(8) 1.913(3) -0.1779(8) 0.090(5) Uani 1 1 d . . . H24 H 0.3920 1.8383 -0.1744 0.108 Uiso 1 1 calc R . . C25 C 0.3183(10) 2.086(3) -0.2169(7) 0.086(5) Uani 1 1 d . . . H25 H 0.3434 2.1127 -0.2422 0.104 Uiso 1 1 calc R . . N2 N 0.3775(11) 1.279(3) -0.0185(6) 0.099(5) Uani 1 1 d . . . N3 N 0.2583(8) 2.224(3) -0.2238(5) 0.087(4) Uani 1 1 d . . . C26 C 0.1181(12) 0.187(4) -0.0484(8) 0.118(7) Uani 1 1 d . . . H26 H 0.1254 0.3059 -0.0719 0.141 Uiso 1 1 calc R . . C27 C 0.0498(10) 0.178(3) -0.0379(8) 0.098(6) Uani 1 1 d . . . H27 H 0.0141 0.2963 -0.0534 0.118 Uiso 1 1 calc R . . C28 C 0.0351(7) 0.009(3) -0.0071(6) 0.061(4) Uani 1 1 d . . . C29 C 0.0938(9) -0.150(3) 0.0192(7) 0.080(5) Uani 1 1 d . . . H29 H 0.0890 -0.2641 0.0447 0.096 Uiso 1 1 calc R . . C30 C 0.1588(8) -0.136(3) 0.0071(7) 0.075(5) Uani 1 1 d . . . H30 H 0.1959 -0.2501 0.0228 0.090 Uiso 1 1 calc R . . N4 N 0.1708(8) 0.030(3) -0.0256(6) 0.091(4) 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 Cl1 0.074(3) 0.086(3) 0.126(4) 0.017(3) 0.028(2) -0.012(3) C1 0.089(13) 0.054(12) 0.135(16) 0.013(11) 0.062(12) 0.026(10) C2 0.110(14) 0.048(10) 0.073(11) -0.010(9) 0.037(10) 0.014(10) C3 0.072(11) 0.044(10) 0.077(11) 0.013(9) 0.008(9) 0.013(10) C4 0.065(11) 0.055(11) 0.073(11) 0.013(9) 0.014(9) 0.000(9) C5 0.081(11) 0.043(9) 0.072(11) -0.006(8) 0.017(9) 0.011(9) C6 0.066(11) 0.094(13) 0.066(11) -0.013(11) 0.021(9) -0.026(10) C7 0.055(10) 0.097(13) 0.089(12) -0.031(11) 0.028(9) -0.007(10) C8 0.101(13) 0.086(13) 0.078(12) 0.000(10) 0.033(11) 0.016(12) C9 0.080(12) 0.045(10) 0.061(10) -0.003(8) 0.018(9) 0.007(9) C10 0.070(11) 0.074(12) 0.112(13) -0.002(11) 0.058(10) 0.004(11) C11 0.090(12) 0.052(10) 0.068(10) 0.011(9) 0.027(9) 0.002(10) C12 0.084(12) 0.029(9) 0.113(13) 0.013(9) 0.048(10) 0.014(9) C13 0.088(13) 0.077(12) 0.097(14) 0.053(11) 0.011(11) 0.037(10) C14 0.100(14) 0.107(15) 0.134(17) 0.014(14) 0.055(13) 0.000(12) C15 0.072(13) 0.115(18) 0.093(14) 0.054(15) 0.038(12) 0.037(12) N1 0.056(8) 0.050(7) 0.098(10) -0.011(7) 0.021(7) -0.006(7) O1 0.117(12) 0.080(10) 0.243(19) 0.034(11) 0.018(11) -0.014(9) O2 0.191(14) 0.065(8) 0.125(11) 0.047(9) 0.039(11) -0.012(9) C16 0.133(18) 0.129(18) 0.119(17) 0.079(15) 0.057(15) -0.036(15) C17 0.067(11) 0.135(17) 0.127(16) 0.037(15) 0.053(12) 0.010(12) C18 0.048(9) 0.049(9) 0.090(11) -0.002(9) 0.019(9) -0.028(8) C19 0.055(11) 0.153(19) 0.150(18) 0.065(16) 0.054(11) 0.046(12) C20 0.17(2) 0.125(18) 0.15(2) 0.098(17) 0.099(18) 0.085(16) C21 0.102(9) 0.111(10) 0.110(10) 0.008(8) 0.046(8) 0.012(8) C22 0.163(18) 0.088(13) 0.136(17) 0.052(13) 0.105(15) 0.044(14) C23 0.084(11) 0.046(9) 0.100(12) -0.001(9) 0.048(10) -0.001(9) C24 0.054(10) 0.101(14) 0.117(14) 0.035(12) 0.031(10) 0.015(10) C25 0.092(13) 0.076(12) 0.092(13) 0.010(11) 0.033(11) 0.021(11) N2 0.148(15) 0.071(10) 0.063(10) 0.012(8) 0.016(10) 0.011(11) N3 0.102(10) 0.083(10) 0.075(9) 0.012(8) 0.030(8) -0.002(9) C26 0.118(16) 0.102(17) 0.150(19) 0.047(15) 0.067(15) -0.015(15) C27 0.114(15) 0.048(11) 0.139(16) 0.046(11) 0.053(13) 0.024(10) C28 0.057(10) 0.056(9) 0.059(9) 0.016(8) 0.008(8) 0.011(9) C29 0.065(10) 0.075(12) 0.105(13) 0.024(10) 0.033(10) 0.005(10) C30 0.054(11) 0.059(10) 0.109(13) 0.032(10) 0.023(9) 0.013(8) N4 0.087(11) 0.085(11) 0.107(11) 0.018(10) 0.041(9) 0.015(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl1 C6 1.766(14) . ? C1 C12 1.34(2) . ? C1 C2 1.408(19) . ? C1 H1 0.9300 . ? C2 C3 1.380(18) . ? C2 H2 0.9300 . ? C3 C10 1.37(2) . ? C3 C4 1.46(2) . ? C4 C5 1.367(18) . ? C4 C9 1.412(19) . ? C5 C6 1.364(18) . ? C5 H5 0.9300 . ? C6 C7 1.35(2) . ? C7 C8 1.39(2) . ? C7 H7 0.9300 . ? C8 C9 1.416(19) . ? C8 H8 0.9300 . ? C9 N1 1.374(16) . ? C10 N1 1.397(17) . ? C10 C11 1.397(18) . ? C11 C12 1.367(18) . ? C11 H11 0.9300 . ? C12 C13 1.57(2) . ? C13 C14 1.401(19) . ? C13 C15 1.47(2) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O2 1.234(19) . ? C15 O1 1.24(2) . ? N1 H1N 0.8600 . ? O2 H2O 0.8200 . ? C16 N2 1.32(2) . ? C16 C17 1.35(2) . ? C16 H16 0.9300 . ? C17 C18 1.330(18) . ? C17 H17 0.9300 . ? C18 C19 1.355(18) . ? C18 C23 1.537(19) . ? C19 C20 1.31(2) . ? C19 H19 0.9300 . ? C20 N2 1.32(2) . ? C20 H20 0.9300 . ? C21 N3 1.304(19) . ? C21 C22 1.38(2) . ? C21 H21 0.9300 . ? C22 C23 1.36(2) . ? C22 H22 0.9300 . ? C23 C24 1.383(19) . ? C24 C25 1.35(2) . ? C24 H24 0.9300 . ? C25 N3 1.336(18) . ? C25 H25 0.9300 . ? C26 N4 1.30(2) . ? C26 C27 1.41(2) . ? C26 H26 0.9300 . ? C27 C28 1.307(18) . ? C27 H27 0.9300 . ? C28 C29 1.398(18) . ? C28 C28 1.50(3) 3 ? C29 C30 1.374(17) . ? C29 H29 0.9300 . ? C30 N4 1.308(17) . ? C30 H30 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C1 C2 121.6(14) . . ? C12 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C3 C2 C1 117.0(15) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C10 C3 C2 120.3(15) . . ? C10 C3 C4 106.2(14) . . ? C2 C3 C4 133.5(16) . . ? C5 C4 C9 120.1(15) . . ? C5 C4 C3 134.0(16) . . ? C9 C4 C3 105.6(14) . . ? C6 C5 C4 118.5(14) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.8 . . ? C7 C6 C5 123.5(14) . . ? C7 C6 Cl1 117.5(13) . . ? C5 C6 Cl1 119.0(14) . . ? C6 C7 C8 120.3(14) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C9 117.5(15) . . ? C7 C8 H8 121.3 . . ? C9 C8 H8 121.3 . . ? N1 C9 C4 110.2(13) . . ? N1 C9 C8 129.7(15) . . ? C4 C9 C8 120.0(15) . . ? C3 C10 N1 111.0(13) . . ? C3 C10 C11 121.6(15) . . ? N1 C10 C11 127.3(16) . . ? C12 C11 C10 117.0(15) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? C1 C12 C11 122.2(15) . . ? C1 C12 C13 120.4(15) . . ? C11 C12 C13 117.2(15) . . ? C14 C13 C15 120.1(17) . . ? C14 C13 C12 114.6(14) . . ? C15 C13 C12 112.6(13) . . ? C14 C13 H13 102.0 . . ? C15 C13 H13 102.1 . . ? C12 C13 H13 102.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 O1 117.7(19) . . ? O2 C15 C13 120(2) . . ? O1 C15 C13 121.7(19) . . ? C9 N1 C10 106.9(12) . . ? C9 N1 H1N 126.6 . . ? C10 N1 H1N 126.6 . . ? C15 O2 H2O 109.5 . . ? N2 C16 C17 125.1(17) . . ? N2 C16 H16 117.5 . . ? C17 C16 H16 117.4 . . ? C18 C17 C16 121.0(17) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 114.9(16) . . ? C17 C18 C23 122.4(15) . . ? C19 C18 C23 122.7(15) . . ? C20 C19 C18 120.1(17) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 120.0 . . ? C19 C20 N2 127.8(19) . . ? C19 C20 H20 116.1 . . ? N2 C20 H20 116.1 . . ? N3 C21 C22 129.6(17) . . ? N3 C21 H21 115.2 . . ? C22 C21 H21 115.2 . . ? C23 C22 C21 116.7(15) . . ? C23 C22 H22 121.6 . . ? C21 C22 H22 121.7 . . ? C22 C23 C24 117.1(15) . . ? C22 C23 C18 119.1(14) . . ? C24 C23 C18 123.4(15) . . ? C25 C24 C23 118.2(15) . . ? C25 C24 H24 120.9 . . ? C23 C24 H24 120.9 . . ? N3 C25 C24 127.8(16) . . ? N3 C25 H25 116.1 . . ? C24 C25 H25 116.1 . . ? C20 N2 C16 110.9(15) . . ? C21 N3 C25 110.1(15) . . ? N4 C26 C27 120.7(16) . . ? N4 C26 H26 119.7 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 122.5(15) . . ? C28 C27 H27 118.7 . . ? C26 C27 H27 118.8 . . ? C27 C28 C29 115.6(13) . . ? C27 C28 C28 125.5(18) . 3 ? C29 C28 C28 118.4(17) . 3 ? C30 C29 C28 119.4(14) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? N4 C30 C29 123.2(14) . . ? N4 C30 H30 118.4 . . ? C29 C30 H30 118.4 . . ? C26 N4 C30 118.1(14) . . ? 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 C12 C1 C2 C3 -6(2) . . . . ? C1 C2 C3 C10 4(2) . . . . ? C1 C2 C3 C4 -179.2(14) . . . . ? C10 C3 C4 C5 -177.1(16) . . . . ? C2 C3 C4 C5 6(3) . . . . ? C10 C3 C4 C9 -2.6(15) . . . . ? C2 C3 C4 C9 -179.7(15) . . . . ? C9 C4 C5 C6 3(2) . . . . ? C3 C4 C5 C6 176.7(15) . . . . ? C4 C5 C6 C7 -3(2) . . . . ? C4 C5 C6 Cl1 175.6(11) . . . . ? C5 C6 C7 C8 1(2) . . . . ? Cl1 C6 C7 C8 -177.7(12) . . . . ? C6 C7 C8 C9 1(2) . . . . ? C5 C4 C9 N1 177.5(12) . . . . ? C3 C4 C9 N1 2.1(15) . . . . ? C5 C4 C9 C8 0(2) . . . . ? C3 C4 C9 C8 -175.8(13) . . . . ? C7 C8 C9 N1 -179.0(14) . . . . ? C7 C8 C9 C4 -2(2) . . . . ? C2 C3 C10 N1 179.8(13) . . . . ? C4 C3 C10 N1 2.3(17) . . . . ? C2 C3 C10 C11 -1(2) . . . . ? C4 C3 C10 C11 -178.8(13) . . . . ? C3 C10 C11 C12 0(2) . . . . ? N1 C10 C11 C12 178.8(14) . . . . ? C2 C1 C12 C11 5(3) . . . . ? C2 C1 C12 C13 179.8(13) . . . . ? C10 C11 C12 C1 -2(2) . . . . ? C10 C11 C12 C13 -176.7(13) . . . . ? C1 C12 C13 C14 -101(2) . . . . ? C11 C12 C13 C14 73.6(19) . . . . ? C1 C12 C13 C15 116.8(19) . . . . ? C11 C12 C13 C15 -68(2) . . . . ? C14 C13 C15 O2 163.1(17) . . . . ? C12 C13 C15 O2 -57(2) . . . . ? C14 C13 C15 O1 -21(3) . . . . ? C12 C13 C15 O1 118(2) . . . . ? C4 C9 N1 C10 -0.7(15) . . . . ? C8 C9 N1 C10 176.9(15) . . . . ? C3 C10 N1 C9 -1.0(17) . . . . ? C11 C10 N1 C9 -179.9(14) . . . . ? N2 C16 C17 C18 1(3) . . . . ? C16 C17 C18 C19 -2(3) . . . . ? C16 C17 C18 C23 176.6(16) . . . . ? C17 C18 C19 C20 0(3) . . . . ? C23 C18 C19 C20 -178.5(18) . . . . ? C18 C19 C20 N2 3(4) . . . . ? N3 C21 C22 C23 1(3) . . . . ? C21 C22 C23 C24 5(3) . . . . ? C21 C22 C23 C18 178.2(15) . . . . ? C17 C18 C23 C22 15(2) . . . . ? C19 C18 C23 C22 -166.1(18) . . . . ? C17 C18 C23 C24 -171.9(17) . . . . ? C19 C18 C23 C24 7(2) . . . . ? C22 C23 C24 C25 -8(2) . . . . ? C18 C23 C24 C25 178.8(14) . . . . ? C23 C24 C25 N3 6(3) . . . . ? C19 C20 N2 C16 -4(3) . . . . ? C17 C16 N2 C20 2(3) . . . . ? C22 C21 N3 C25 -3(3) . . . . ? C24 C25 N3 C21 -1(2) . . . . ? N4 C26 C27 C28 -3(3) . . . . ? C26 C27 C28 C29 6(3) . . . . ? C26 C27 C28 C28 178.3(18) . . . 3 ? C27 C28 C29 C30 -7(2) . . . . ? C28 C28 C29 C30 -179.6(16) 3 . . . ? C28 C29 C30 N4 4(2) . . . . ? C27 C26 N4 C30 0(3) . . . . ? C29 C30 N4 C26 -1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 20.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.260 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.066 # Attachment '- triclinic_cocrystal.cif' data_2:1 _database_code_depnum_ccdc_archive 'CCDC 826307' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C15 H12 Cl N O2), C10 H8 N2' _chemical_formula_sum 'C40 H32 Cl2 N4 O4' _chemical_formula_weight 703.60 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' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2681(9) _cell_length_b 12.4755(16) _cell_length_c 16.074(3) _cell_angle_alpha 73.308(12) _cell_angle_beta 82.774(14) _cell_angle_gamma 75.228(9) _cell_volume 1718.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 16 _exptl_crystal_description PRISM _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9778 _exptl_absorpt_correction_T_max 0.9997 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 300 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6441 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6030 _reflns_number_gt 4109 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0460P)^2^+0.7452P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6030 _refine_ls_number_parameters 465 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.62695(9) 0.67468(7) 0.83884(6) 0.0776(3) Uani 1 1 d . . . Cl2 Cl 0.11187(10) 0.60393(8) 0.56635(6) 0.0916(3) Uani 1 1 d . . . C1 C 1.1507(3) 0.6852(3) 1.14433(18) 0.0668(8) Uani 1 1 d . . . H1 H 1.1218 0.7056 1.1963 0.080 Uiso 1 1 calc R . . C2 C 1.0423(3) 0.6831(3) 1.09429(19) 0.0662(8) Uani 1 1 d . . . H2 H 0.9420 0.7001 1.1129 0.079 Uiso 1 1 calc R . . C3 C 1.0841(3) 0.6554(2) 1.01554(16) 0.0535(7) Uani 1 1 d . . . C4 C 1.0036(3) 0.6463(2) 0.94765(17) 0.0528(7) Uani 1 1 d . . . C5 C 0.8531(3) 0.6637(2) 0.93454(18) 0.0573(7) Uani 1 1 d . . . H5 H 0.7797 0.6847 0.9757 0.069 Uiso 1 1 calc R . . C6 C 0.8158(3) 0.6491(2) 0.85923(19) 0.0591(7) Uani 1 1 d . . . C7 C 0.9230(3) 0.6138(3) 0.79801(19) 0.0671(8) Uani 1 1 d . . . H7 H 0.8936 0.6018 0.7488 0.081 Uiso 1 1 calc R . . C8 C 1.0721(3) 0.5965(3) 0.80973(19) 0.0693(8) Uani 1 1 d . . . H8 H 1.1446 0.5741 0.7686 0.083 Uiso 1 1 calc R . . C9 C 1.1116(3) 0.6133(2) 0.88452(17) 0.0574(7) Uani 1 1 d . . . C10 C 1.2370(3) 0.6282(2) 0.99094(16) 0.0540(7) Uani 1 1 d . . . C11 C 1.3469(3) 0.6288(2) 1.04214(17) 0.0575(7) Uani 1 1 d . . . H11 H 1.4475 0.6101 1.0246 0.069 Uiso 1 1 calc R . . C12 C 1.3031(3) 0.6578(2) 1.11989(17) 0.0568(7) Uani 1 1 d . . . C13 C 1.4155(3) 0.6572(2) 1.18134(17) 0.0600(7) Uani 1 1 d . . . H13 H 1.3659 0.7104 1.2163 0.072 Uiso 1 1 calc R . . C14 C 1.4531(3) 0.5374(2) 1.24264(17) 0.0528(6) Uani 1 1 d . . . C15 C 1.5581(4) 0.6928(3) 1.1388(2) 0.0837(10) Uani 1 1 d . . . H15A H 1.6205 0.6905 1.1829 0.126 Uiso 1 1 calc R . . H15B H 1.5335 0.7694 1.1013 0.126 Uiso 1 1 calc R . . H15C H 1.6105 0.6408 1.1052 0.126 Uiso 1 1 calc R . . C16 C 0.7961(3) 0.1382(3) 0.63623(19) 0.0635(8) Uani 1 1 d . . . H16 H 0.8925 0.1481 0.6191 0.076 Uiso 1 1 calc R . . C17 C 0.6778(3) 0.2330(3) 0.61928(18) 0.0607(7) Uani 1 1 d . . . H17 H 0.6942 0.3058 0.5920 0.073 Uiso 1 1 calc R . . C18 C 0.5330(3) 0.2176(2) 0.64391(17) 0.0521(6) Uani 1 1 d . . . C19 C 0.3867(3) 0.2944(2) 0.63715(16) 0.0522(6) Uani 1 1 d . . . C20 C 0.3338(3) 0.4121(3) 0.60396(18) 0.0612(7) Uani 1 1 d . . . H20 H 0.3994 0.4599 0.5804 0.073 Uiso 1 1 calc R . . C21 C 0.1814(3) 0.4564(3) 0.60687(18) 0.0641(8) Uani 1 1 d . . . C22 C 0.0812(3) 0.3869(3) 0.6416(2) 0.0703(8) Uani 1 1 d . . . H22 H -0.0209 0.4196 0.6421 0.084 Uiso 1 1 calc R . . C23 C 0.1313(3) 0.2703(3) 0.67528(19) 0.0664(8) Uani 1 1 d . . . H23 H 0.0647 0.2233 0.6989 0.080 Uiso 1 1 calc R . . C24 C 0.2845(3) 0.2251(3) 0.67284(17) 0.0554(7) Uani 1 1 d . . . C25 C 0.5132(3) 0.1063(2) 0.68459(17) 0.0529(7) Uani 1 1 d . . . C26 C 0.6332(3) 0.0114(2) 0.70220(18) 0.0566(7) Uani 1 1 d . . . H26 H 0.6175 -0.0615 0.7296 0.068 Uiso 1 1 calc R . . C27 C 0.7756(3) 0.0274(2) 0.67846(19) 0.0581(7) Uani 1 1 d . . . C28 C 0.9102(3) -0.0747(3) 0.6971(2) 0.0656(8) Uani 1 1 d . . . H28 H 0.8741 -0.1410 0.7342 0.079 Uiso 1 1 calc R . . C29 C 1.0200(3) -0.0507(2) 0.7472(2) 0.0580(7) Uani 1 1 d . . . C30 C 0.9854(4) -0.1064(3) 0.6163(2) 0.0933(11) Uani 1 1 d . . . H30A H 1.0193 -0.0420 0.5779 0.140 Uiso 1 1 calc R . . H30B H 0.9156 -0.1269 0.5878 0.140 Uiso 1 1 calc R . . H30C H 1.0692 -0.1704 0.6317 0.140 Uiso 1 1 calc R . . C31 C 1.1720(4) 0.0328(3) 0.9669(3) 0.1018(13) Uani 1 1 d . . . H31 H 1.0766 0.0720 0.9809 0.122 Uiso 1 1 calc R . . C32 C 1.2904(4) 0.0465(3) 1.0023(3) 0.0971(13) Uani 1 1 d . . . H32 H 1.2736 0.0928 1.0404 0.117 Uiso 1 1 calc R . . C33 C 1.4343(3) -0.0076(2) 0.98216(18) 0.0616(7) Uani 1 1 d . . . C34 C 1.4480(4) -0.0762(3) 0.9270(2) 0.0845(11) Uani 1 1 d . . . H34 H 1.5421 -0.1151 0.9107 0.101 Uiso 1 1 calc R . . C35 C 1.3220(4) -0.0874(3) 0.8959(2) 0.0885(11) Uani 1 1 d . . . H35 H 1.3347 -0.1364 0.8601 0.106 Uiso 1 1 calc R . . C36 C 1.3178(3) 0.2495(2) 1.45175(18) 0.0580(7) Uani 1 1 d . . . H36 H 1.2246 0.2949 1.4624 0.070 Uiso 1 1 calc R . . C37 C 1.3455(3) 0.1337(2) 1.49245(17) 0.0525(6) Uani 1 1 d . . . H37 H 1.2717 0.1030 1.5291 0.063 Uiso 1 1 calc R . . C38 C 1.4828(3) 0.0625(2) 1.47907(15) 0.0454(6) Uani 1 1 d . . . C39 C 1.5845(3) 0.1164(3) 1.4229(2) 0.0707(8) Uani 1 1 d . . . H39 H 1.6788 0.0736 1.4110 0.085 Uiso 1 1 calc R . . C40 C 1.5472(3) 0.2321(3) 1.3848(2) 0.0759(9) Uani 1 1 d . . . H40 H 1.6181 0.2653 1.3471 0.091 Uiso 1 1 calc R . . N1 N 1.2517(3) 0.6028(2) 0.91148(15) 0.0639(6) Uani 1 1 d D . . H1N H 1.3442(18) 0.583(2) 0.8799(16) 0.077 Uiso 1 1 d D . . N2 N 0.3620(2) 0.1120(2) 0.70225(15) 0.0596(6) Uani 1 1 d D . . H2N H 0.314(3) 0.0494(17) 0.7219(17) 0.071 Uiso 1 1 d D . . N3 N 1.1860(3) -0.0335(2) 0.91344(17) 0.0768(7) Uani 1 1 d . . . N4 N 1.4159(3) 0.29978(19) 1.39851(14) 0.0588(6) Uani 1 1 d . . . O1 O 1.5629(2) 0.46412(17) 1.23189(12) 0.0643(5) Uani 1 1 d . . . O2 O 1.3541(2) 0.51886(16) 1.30801(12) 0.0652(5) Uani 1 1 d D . . H2O H 1.375(3) 0.4393(11) 1.3401(16) 0.078 Uiso 1 1 d D . . O3 O 1.1382(2) -0.0284(2) 0.71637(13) 0.0763(6) Uani 1 1 d . . . O4 O 0.9736(2) -0.0561(2) 0.82765(15) 0.0864(7) Uani 1 1 d D . . H4O H 1.053(3) -0.043(3) 0.853(2) 0.104 Uiso 1 1 d 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 Cl1 0.0683(5) 0.0764(5) 0.0911(6) -0.0263(4) -0.0062(4) -0.0168(4) Cl2 0.0846(6) 0.0798(6) 0.0912(6) -0.0159(5) -0.0002(5) 0.0048(5) C1 0.074(2) 0.073(2) 0.0485(17) -0.0227(15) 0.0089(15) -0.0078(16) C2 0.0630(18) 0.072(2) 0.0588(18) -0.0233(15) 0.0143(15) -0.0092(15) C3 0.0610(17) 0.0480(15) 0.0449(15) -0.0099(12) 0.0080(12) -0.0089(12) C4 0.0592(17) 0.0432(15) 0.0489(15) -0.0084(12) 0.0076(13) -0.0089(12) C5 0.0630(18) 0.0480(16) 0.0559(17) -0.0134(13) 0.0123(13) -0.0118(13) C6 0.0602(17) 0.0473(16) 0.0660(19) -0.0125(14) -0.0003(14) -0.0104(13) C7 0.078(2) 0.0635(19) 0.0615(18) -0.0230(15) -0.0047(15) -0.0115(16) C8 0.070(2) 0.077(2) 0.0604(19) -0.0290(16) 0.0055(15) -0.0080(16) C9 0.0659(18) 0.0524(16) 0.0482(16) -0.0128(13) 0.0046(13) -0.0084(13) C10 0.0632(17) 0.0508(16) 0.0426(15) -0.0118(12) 0.0105(13) -0.0107(13) C11 0.0596(17) 0.0534(17) 0.0531(16) -0.0097(13) 0.0064(13) -0.0116(13) C12 0.0726(19) 0.0463(15) 0.0456(15) -0.0077(12) 0.0061(13) -0.0132(13) C13 0.0743(19) 0.0537(17) 0.0506(16) -0.0115(13) 0.0030(14) -0.0180(14) C14 0.0578(17) 0.0569(17) 0.0472(15) -0.0174(13) 0.0026(12) -0.0183(14) C15 0.108(3) 0.086(2) 0.063(2) -0.0076(17) -0.0003(18) -0.049(2) C16 0.0409(15) 0.077(2) 0.079(2) -0.0283(17) 0.0032(13) -0.0202(14) C17 0.0551(17) 0.0650(19) 0.0682(19) -0.0209(15) 0.0015(14) -0.0237(14) C18 0.0451(14) 0.0649(18) 0.0534(16) -0.0234(14) -0.0003(12) -0.0176(13) C19 0.0482(15) 0.0648(18) 0.0502(15) -0.0237(14) -0.0002(12) -0.0163(13) C20 0.0586(17) 0.076(2) 0.0552(17) -0.0244(15) 0.0009(13) -0.0201(15) C21 0.0606(18) 0.071(2) 0.0567(17) -0.0216(15) -0.0040(14) -0.0031(15) C22 0.0498(17) 0.089(2) 0.070(2) -0.0308(18) 0.0023(15) -0.0034(16) C23 0.0498(17) 0.084(2) 0.0695(19) -0.0301(17) 0.0078(14) -0.0175(15) C24 0.0448(15) 0.074(2) 0.0532(16) -0.0271(14) 0.0018(12) -0.0158(14) C25 0.0443(15) 0.0695(19) 0.0541(16) -0.0250(14) 0.0024(12) -0.0223(13) C26 0.0488(16) 0.0591(17) 0.0682(18) -0.0211(14) -0.0031(13) -0.0188(13) C27 0.0496(16) 0.0606(18) 0.0726(19) -0.0259(15) -0.0025(13) -0.0190(13) C28 0.0480(16) 0.0664(19) 0.088(2) -0.0292(17) 0.0003(15) -0.0153(14) C29 0.0465(16) 0.0567(17) 0.0698(19) -0.0186(14) -0.0003(14) -0.0096(13) C30 0.075(2) 0.107(3) 0.116(3) -0.062(2) -0.019(2) -0.010(2) C31 0.081(3) 0.101(3) 0.144(4) -0.064(3) 0.037(2) -0.043(2) C32 0.085(3) 0.105(3) 0.133(3) -0.076(3) 0.043(2) -0.052(2) C33 0.081(2) 0.0432(15) 0.0520(17) -0.0049(13) 0.0088(14) -0.0134(14) C34 0.089(2) 0.091(2) 0.061(2) -0.0341(18) -0.0258(18) 0.0267(19) C35 0.102(3) 0.091(3) 0.066(2) -0.0313(19) -0.036(2) 0.018(2) C36 0.0496(16) 0.0596(18) 0.0584(17) -0.0145(14) -0.0024(13) -0.0032(13) C37 0.0431(14) 0.0591(17) 0.0528(16) -0.0131(13) 0.0009(11) -0.0111(12) C38 0.0432(14) 0.0524(14) 0.0424(14) -0.0148(11) -0.0042(11) -0.0106(12) C39 0.0507(16) 0.0588(19) 0.084(2) -0.0057(16) 0.0154(15) -0.0044(14) C40 0.067(2) 0.063(2) 0.082(2) -0.0044(17) 0.0179(16) -0.0145(16) N1 0.0572(15) 0.0794(17) 0.0543(14) -0.0264(13) 0.0094(11) -0.0103(12) N2 0.0472(13) 0.0668(17) 0.0675(15) -0.0182(13) 0.0035(11) -0.0208(12) N3 0.090(2) 0.0723(18) 0.0649(17) -0.0134(14) -0.0013(14) -0.0195(15) N4 0.0611(14) 0.0533(14) 0.0547(14) -0.0088(11) -0.0001(11) -0.0082(11) O1 0.0575(12) 0.0690(13) 0.0589(12) -0.0157(10) 0.0095(9) -0.0088(10) O2 0.0699(12) 0.0554(12) 0.0570(12) -0.0093(9) 0.0189(10) -0.0081(10) O3 0.0544(12) 0.1135(18) 0.0731(14) -0.0331(13) 0.0075(10) -0.0366(12) O4 0.0740(15) 0.120(2) 0.0720(15) -0.0312(14) 0.0137(12) -0.0360(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl1 C6 1.752(3) . ? Cl2 C21 1.744(3) . ? C1 C2 1.373(4) . ? C1 C12 1.399(4) . ? C1 H1 0.9300 . ? C2 C3 1.390(4) . ? C2 H2 0.9300 . ? C3 C10 1.403(4) . ? C3 C4 1.442(4) . ? C4 C5 1.389(4) . ? C4 C9 1.405(3) . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 C7 1.389(4) . ? C7 C8 1.371(4) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 N1 1.383(4) . ? C10 N1 1.384(3) . ? C10 C11 1.390(4) . ? C11 C12 1.384(4) . ? C11 H11 0.9300 . ? C12 C13 1.521(4) . ? C13 C14 1.517(4) . ? C13 C15 1.519(4) . ? C13 H13 0.9800 . ? C14 O1 1.214(3) . ? C14 O2 1.314(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.380(4) . ? C16 C27 1.404(4) . ? C16 H16 0.9300 . ? C17 C18 1.396(3) . ? C17 H17 0.9300 . ? C18 C25 1.403(4) . ? C18 C19 1.443(4) . ? C19 C20 1.389(4) . ? C19 C24 1.403(4) . ? C20 C21 1.379(4) . ? C20 H20 0.9300 . ? C21 C22 1.388(4) . ? C22 C23 1.375(4) . ? C22 H22 0.9300 . ? C23 C24 1.388(4) . ? C23 H23 0.9300 . ? C24 N2 1.384(4) . ? C25 N2 1.382(3) . ? C25 C26 1.390(4) . ? C26 C27 1.375(4) . ? C26 H26 0.9300 . ? C27 C28 1.527(4) . ? C28 C30 1.501(4) . ? C28 C29 1.508(4) . ? C28 H28 0.9800 . ? C29 O3 1.209(3) . ? C29 O4 1.299(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 N3 1.328(4) . ? C31 C32 1.366(5) . ? C31 H31 0.9300 . ? C32 C33 1.378(4) . ? C32 H32 0.9300 . ? C33 C34 1.374(4) . ? C33 C33 1.484(6) 2_857 ? C34 C35 1.379(5) . ? C34 H34 0.9300 . ? C35 N3 1.307(4) . ? C35 H35 0.9300 . ? C36 N4 1.319(3) . ? C36 C37 1.375(4) . ? C36 H36 0.9300 . ? C37 C38 1.386(3) . ? C37 H37 0.9300 . ? C38 C39 1.384(4) . ? C38 C38 1.479(5) 2_858 ? C39 C40 1.367(4) . ? C39 H39 0.9300 . ? C40 N4 1.326(4) . ? C40 H40 0.9300 . ? N1 H1N 0.952(10) . ? N2 H2N 0.950(10) . ? O2 H2O 0.961(10) . ? O4 H4O 0.956(10) . ? 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 C2 C1 C12 122.3(3) . . ? C2 C1 H1 118.8 . . ? C12 C1 H1 118.8 . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C10 118.3(3) . . ? C2 C3 C4 134.4(3) . . ? C10 C3 C4 107.3(2) . . ? C5 C4 C9 119.3(3) . . ? C5 C4 C3 134.1(2) . . ? C9 C4 C3 106.5(2) . . ? C6 C5 C4 118.2(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C7 122.2(3) . . ? C5 C6 Cl1 119.5(2) . . ? C7 C6 Cl1 118.3(2) . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 118.1(3) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? N1 C9 C8 129.7(3) . . ? N1 C9 C4 108.6(2) . . ? C8 C9 C4 121.7(3) . . ? N1 C10 C11 129.5(2) . . ? N1 C10 C3 108.2(2) . . ? C11 C10 C3 122.4(2) . . ? C12 C11 C10 118.5(3) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C1 119.2(3) . . ? C11 C12 C13 122.1(3) . . ? C1 C12 C13 118.7(2) . . ? C14 C13 C15 110.0(2) . . ? C14 C13 C12 107.6(2) . . ? C15 C13 C12 116.1(2) . . ? C14 C13 H13 107.6 . . ? C15 C13 H13 107.6 . . ? C12 C13 H13 107.6 . . ? O1 C14 O2 122.7(2) . . ? O1 C14 C13 123.5(2) . . ? O2 C14 C13 113.9(2) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C27 122.2(2) . . ? C17 C16 H16 118.9 . . ? C27 C16 H16 118.9 . . ? C16 C17 C18 118.7(3) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C17 C18 C25 118.8(2) . . ? C17 C18 C19 133.9(3) . . ? C25 C18 C19 107.3(2) . . ? C20 C19 C24 119.3(2) . . ? C20 C19 C18 134.6(2) . . ? C24 C19 C18 106.1(2) . . ? C21 C20 C19 118.3(3) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C20 C21 C22 121.9(3) . . ? C20 C21 Cl2 119.3(2) . . ? C22 C21 Cl2 118.8(2) . . ? C23 C22 C21 120.7(3) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 117.7(3) . . ? C22 C23 H23 121.2 . . ? C24 C23 H23 121.2 . . ? N2 C24 C23 128.7(3) . . ? N2 C24 C19 109.2(2) . . ? C23 C24 C19 122.0(3) . . ? N2 C25 C26 129.4(3) . . ? N2 C25 C18 108.5(2) . . ? C26 C25 C18 122.1(2) . . ? C27 C26 C25 118.8(3) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? C26 C27 C16 119.4(3) . . ? C26 C27 C28 120.3(3) . . ? C16 C27 C28 120.3(2) . . ? C30 C28 C29 110.8(2) . . ? C30 C28 C27 113.0(3) . . ? C29 C28 C27 110.1(2) . . ? C30 C28 H28 107.6 . . ? C29 C28 H28 107.6 . . ? C27 C28 H28 107.6 . . ? O3 C29 O4 123.3(3) . . ? O3 C29 C28 124.2(3) . . ? O4 C29 C28 112.5(2) . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N3 C31 C32 123.5(3) . . ? N3 C31 H31 118.2 . . ? C32 C31 H31 118.2 . . ? C31 C32 C33 120.6(3) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 115.6(3) . . ? C34 C33 C33 122.4(3) . 2_857 ? C32 C33 C33 122.0(3) . 2_857 ? C33 C34 C35 120.0(3) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? N3 C35 C34 124.1(3) . . ? N3 C35 H35 117.9 . . ? C34 C35 H35 117.9 . . ? N4 C36 C37 123.7(2) . . ? N4 C36 H36 118.2 . . ? C37 C36 H36 118.2 . . ? C36 C37 C38 120.3(2) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? C39 C38 C37 115.3(2) . . ? C39 C38 C38 122.5(3) . 2_858 ? C37 C38 C38 122.2(3) . 2_858 ? C40 C39 C38 120.5(3) . . ? C40 C39 H39 119.7 . . ? C38 C39 H39 119.7 . . ? N4 C40 C39 123.8(3) . . ? N4 C40 H40 118.1 . . ? C39 C40 H40 118.1 . . ? C9 N1 C10 109.4(2) . . ? C9 N1 H1N 125.8(17) . . ? C10 N1 H1N 124.8(18) . . ? C25 N2 C24 108.9(2) . . ? C25 N2 H2N 127.2(17) . . ? C24 N2 H2N 123.1(17) . . ? C35 N3 C31 116.1(3) . . ? C36 N4 C40 116.4(2) . . ? C14 O2 H2O 110.8(17) . . ? C29 O4 H4O 105(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 C12 C1 C2 C3 -1.5(5) . . . . ? C1 C2 C3 C10 1.3(4) . . . . ? C1 C2 C3 C4 -179.1(3) . . . . ? C2 C3 C4 C5 1.3(5) . . . . ? C10 C3 C4 C5 -179.1(3) . . . . ? C2 C3 C4 C9 -179.4(3) . . . . ? C10 C3 C4 C9 0.2(3) . . . . ? C9 C4 C5 C6 -0.7(4) . . . . ? C3 C4 C5 C6 178.5(3) . . . . ? C4 C5 C6 C7 2.3(4) . . . . ? C4 C5 C6 Cl1 -178.0(2) . . . . ? C5 C6 C7 C8 -2.5(4) . . . . ? Cl1 C6 C7 C8 177.8(2) . . . . ? C6 C7 C8 C9 1.1(4) . . . . ? C7 C8 C9 N1 -179.4(3) . . . . ? C7 C8 C9 C4 0.5(4) . . . . ? C5 C4 C9 N1 179.3(2) . . . . ? C3 C4 C9 N1 -0.2(3) . . . . ? C5 C4 C9 C8 -0.7(4) . . . . ? C3 C4 C9 C8 179.9(3) . . . . ? C2 C3 C10 N1 179.5(2) . . . . ? C4 C3 C10 N1 -0.2(3) . . . . ? C2 C3 C10 C11 -0.4(4) . . . . ? C4 C3 C10 C11 179.9(2) . . . . ? N1 C10 C11 C12 179.8(3) . . . . ? C3 C10 C11 C12 -0.3(4) . . . . ? C10 C11 C12 C1 0.1(4) . . . . ? C10 C11 C12 C13 178.1(2) . . . . ? C2 C1 C12 C11 0.8(4) . . . . ? C2 C1 C12 C13 -177.3(3) . . . . ? C11 C12 C13 C14 -88.9(3) . . . . ? C1 C12 C13 C14 89.0(3) . . . . ? C11 C12 C13 C15 34.7(4) . . . . ? C1 C12 C13 C15 -147.3(3) . . . . ? C15 C13 C14 O1 -29.9(4) . . . . ? C12 C13 C14 O1 97.4(3) . . . . ? C15 C13 C14 O2 151.4(2) . . . . ? C12 C13 C14 O2 -81.3(3) . . . . ? C27 C16 C17 C18 -0.9(4) . . . . ? C16 C17 C18 C25 -0.3(4) . . . . ? C16 C17 C18 C19 179.8(3) . . . . ? C17 C18 C19 C20 -0.1(5) . . . . ? C25 C18 C19 C20 180.0(3) . . . . ? C17 C18 C19 C24 178.9(3) . . . . ? C25 C18 C19 C24 -1.1(3) . . . . ? C24 C19 C20 C21 -0.5(4) . . . . ? C18 C19 C20 C21 178.3(3) . . . . ? C19 C20 C21 C22 -0.1(4) . . . . ? C19 C20 C21 Cl2 179.6(2) . . . . ? C20 C21 C22 C23 0.5(4) . . . . ? Cl2 C21 C22 C23 -179.2(2) . . . . ? C21 C22 C23 C24 -0.3(4) . . . . ? C22 C23 C24 N2 179.9(3) . . . . ? C22 C23 C24 C19 -0.3(4) . . . . ? C20 C19 C24 N2 -179.5(2) . . . . ? C18 C19 C24 N2 1.4(3) . . . . ? C20 C19 C24 C23 0.7(4) . . . . ? C18 C19 C24 C23 -178.4(2) . . . . ? C17 C18 C25 N2 -179.6(2) . . . . ? C19 C18 C25 N2 0.4(3) . . . . ? C17 C18 C25 C26 1.0(4) . . . . ? C19 C18 C25 C26 -179.1(2) . . . . ? N2 C25 C26 C27 -179.7(3) . . . . ? C18 C25 C26 C27 -0.4(4) . . . . ? C25 C26 C27 C16 -0.8(4) . . . . ? C25 C26 C27 C28 179.7(2) . . . . ? C17 C16 C27 C26 1.5(4) . . . . ? C17 C16 C27 C28 -179.0(3) . . . . ? C26 C27 C28 C30 109.6(3) . . . . ? C16 C27 C28 C30 -69.8(3) . . . . ? C26 C27 C28 C29 -125.9(3) . . . . ? C16 C27 C28 C29 54.6(4) . . . . ? C30 C28 C29 O3 19.1(4) . . . . ? C27 C28 C29 O3 -106.6(3) . . . . ? C30 C28 C29 O4 -161.2(3) . . . . ? C27 C28 C29 O4 73.1(3) . . . . ? N3 C31 C32 C33 1.4(6) . . . . ? C31 C32 C33 C34 -1.4(5) . . . . ? C31 C32 C33 C33 178.5(4) . . . 2_857 ? C32 C33 C34 C35 -0.1(5) . . . . ? C33 C33 C34 C35 179.9(3) 2_857 . . . ? C33 C34 C35 N3 2.0(6) . . . . ? N4 C36 C37 C38 0.3(4) . . . . ? C36 C37 C38 C39 -0.4(4) . . . . ? C36 C37 C38 C38 -179.5(3) . . . 2_858 ? C37 C38 C39 C40 0.0(4) . . . . ? C38 C38 C39 C40 179.1(3) 2_858 . . . ? C38 C39 C40 N4 0.5(5) . . . . ? C8 C9 N1 C10 -180.0(3) . . . . ? C4 C9 N1 C10 0.1(3) . . . . ? C11 C10 N1 C9 -180.0(3) . . . . ? C3 C10 N1 C9 0.1(3) . . . . ? C26 C25 N2 C24 179.9(3) . . . . ? C18 C25 N2 C24 0.5(3) . . . . ? C23 C24 N2 C25 178.6(3) . . . . ? C19 C24 N2 C25 -1.2(3) . . . . ? C34 C35 N3 C31 -2.0(5) . . . . ? C32 C31 N3 C35 0.3(6) . . . . ? C37 C36 N4 C40 0.2(4) . . . . ? C39 C40 N4 C36 -0.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.254 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.033 data_bin4_2 _database_code_depnum_ccdc_archive 'CCDC 842706' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 Cl N O2, 1.5(C10 H8 N2)' _chemical_formula_sum 'C30 H24 Cl N4 O2' _chemical_formula_weight 507.98 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' Cl Cl 0.1484 0.1585 '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 'P 21/c' _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 19.0685(15) _cell_length_b 5.5501(5) _cell_length_c 25.148(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.116(2) _cell_angle_gamma 90.00 _cell_volume 2499.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3266 _cell_measurement_theta_min 2 _cell_measurement_theta_max 21 _exptl_crystal_description 'PLATY PRISM' _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _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 'Bruker-Axs Smart-Apex CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21045 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4438 _reflns_number_gt 2716 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker-Axs Inc)' _computing_cell_refinement 'SAINT (Bruker-Axs Inc)' _computing_data_reduction 'SAINT (Bruker-Axs Inc)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0909P)^2^+0.8941P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4438 _refine_ls_number_parameters 341 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1895 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Cl1 Cl -0.05983(5) 0.29026(19) 0.15067(4) 0.0870(4) Uani 1 1 d . . . C1 C 0.3026(2) 0.4228(6) 0.10941(15) 0.0689(9) Uani 1 1 d . . . H1 H 0.3220 0.3123 0.0904 0.083 Uiso 1 1 calc R . . C2 C 0.2344(2) 0.3797(6) 0.11397(14) 0.0644(9) Uani 1 1 d . . . H2 H 0.2078 0.2420 0.0979 0.077 Uiso 1 1 calc R . . C3 C 0.20483(17) 0.5439(5) 0.14296(13) 0.0553(8) Uani 1 1 d . . . C4 C 0.13786(17) 0.5516(5) 0.15666(12) 0.0531(7) Uani 1 1 d . . . C5 C 0.07559(18) 0.4024(5) 0.14540(13) 0.0593(8) Uani 1 1 d . . . H5 H 0.0716 0.2618 0.1244 0.071 Uiso 1 1 calc R . . C6 C 0.02037(19) 0.4680(6) 0.16600(14) 0.0640(9) Uani 1 1 d . . . C7 C 0.0250(2) 0.6775(7) 0.19751(15) 0.0716(10) Uani 1 1 d . . . H7 H -0.0135 0.7171 0.2107 0.086 Uiso 1 1 calc R . . C8 C 0.0857(2) 0.8252(6) 0.20922(14) 0.0673(9) Uani 1 1 d . . . H8 H 0.0894 0.9640 0.2307 0.081 Uiso 1 1 calc R . . C9 C 0.14188(19) 0.7642(5) 0.18842(13) 0.0582(8) Uani 1 1 d . . . C10 C 0.24643(19) 0.7495(5) 0.16616(13) 0.0585(8) Uani 1 1 d . . . C11 C 0.31596(19) 0.7939(6) 0.16120(15) 0.0660(9) Uani 1 1 d . . . H11 H 0.3429 0.9318 0.1768 0.079 Uiso 1 1 calc R . . C12 C 0.34379(19) 0.6273(6) 0.13247(14) 0.0653(9) Uani 1 1 d . . . C13 C 0.4206(2) 0.6603(7) 0.12783(16) 0.0750(10) Uani 1 1 d . . . H13 H 0.4273 0.5280 0.1042 0.090 Uiso 1 1 calc R . . C14 C 0.4824(2) 0.6366(9) 0.18443(18) 0.1010(13) Uani 1 1 d . . . H14A H 0.5299 0.6489 0.1793 0.152 Uiso 1 1 calc R . . H14B H 0.4787 0.4830 0.2008 0.152 Uiso 1 1 calc R . . H14C H 0.4779 0.7628 0.2092 0.152 Uiso 1 1 calc R . . C15 C 0.4257(2) 0.8913(6) 0.09744(17) 0.0656(9) Uani 1 1 d . . . N1 N 0.20715(16) 0.8834(5) 0.19345(12) 0.0656(7) Uani 1 1 d D . . H1N H 0.2262(17) 1.019(4) 0.2178(11) 0.079 Uiso 1 1 d D . . O1 O 0.46281(17) 1.0621(5) 0.11941(15) 0.1153(11) Uani 1 1 d . . . O2 O 0.3841(2) 0.8917(5) 0.04515(14) 0.1125(11) Uani 1 1 d D . . H2O H 0.393(2) 1.034(5) 0.0265(18) 0.135 Uiso 1 1 d D . . C16 C 0.3108(3) 1.3929(9) -0.03298(19) 0.0985(13) Uani 1 1 d . . . H16 H 0.2784 1.3400 -0.0150 0.118 Uiso 1 1 calc R . . C17 C 0.2874(2) 1.5814(8) -0.07135(18) 0.0942(13) Uani 1 1 d . . . H17 H 0.2410 1.6526 -0.0779 0.113 Uiso 1 1 calc R . . C18 C 0.33247(19) 1.6614(6) -0.09934(14) 0.0610(8) Uani 1 1 d . . . C19 C 0.4006(3) 1.5547(8) -0.08515(19) 0.1013(14) Uani 1 1 d . . . H19 H 0.4347 1.6075 -0.1016 0.122 Uiso 1 1 calc R . . C20 C 0.4195(3) 1.3693(9) -0.0466(2) 0.1131(16) Uani 1 1 d . . . H20 H 0.4663 1.2990 -0.0385 0.136 Uiso 1 1 calc R . . C21 C 0.2247(3) 2.1716(8) -0.1892(2) 0.0998(14) Uani 1 1 d . . . H21 H 0.1825 2.2622 -0.1919 0.120 Uiso 1 1 calc R . . C22 C 0.2459(2) 1.9943(8) -0.14839(19) 0.0937(13) Uani 1 1 d . . . H22 H 0.2182 1.9682 -0.1249 0.112 Uiso 1 1 calc R . . C23 C 0.30792(18) 1.8561(6) -0.14233(13) 0.0597(8) Uani 1 1 d . . . C24 C 0.3452(2) 1.9086(7) -0.17867(16) 0.0776(10) Uani 1 1 d . . . H24 H 0.3879 1.8229 -0.1766 0.093 Uiso 1 1 calc R . . C25 C 0.3192(2) 2.0894(7) -0.21853(16) 0.0795(10) Uani 1 1 d . . . H25 H 0.3454 2.1197 -0.2429 0.095 Uiso 1 1 calc R . . N2 N 0.3756(2) 1.2848(5) -0.02045(14) 0.0834(9) Uani 1 1 d . . . N3 N 0.25987(19) 2.2206(5) -0.22413(13) 0.0761(8) Uani 1 1 d . . . C26 C 0.1167(3) 0.1861(8) -0.0480(2) 0.0998(14) Uani 1 1 d . . . H26 H 0.1237 0.3065 -0.0714 0.120 Uiso 1 1 calc R . . C27 C 0.0498(2) 0.1833(7) -0.03885(19) 0.0918(13) Uani 1 1 d . . . H27 H 0.0140 0.3004 -0.0553 0.110 Uiso 1 1 calc R . . C28 C 0.03571(18) 0.0067(5) -0.00525(13) 0.0600(8) Uani 1 1 d . . . C29 C 0.0938(2) -0.1534(6) 0.01761(16) 0.0773(10) Uani 1 1 d . . . H29 H 0.0885 -0.2772 0.0409 0.093 Uiso 1 1 calc R . . C30 C 0.1591(2) -0.1327(7) 0.00656(17) 0.0825(11) Uani 1 1 d . . . H30 H 0.1969 -0.2431 0.0235 0.099 Uiso 1 1 calc R . . N4 N 0.17190(18) 0.0320(6) -0.02627(14) 0.0826(9) 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 Cl1 0.0723(7) 0.0840(7) 0.1028(8) 0.0088(5) 0.0278(5) -0.0120(5) C1 0.079(3) 0.0492(18) 0.084(2) 0.0103(17) 0.036(2) 0.0122(17) C2 0.077(2) 0.0462(17) 0.075(2) 0.0032(16) 0.0331(19) 0.0065(16) C3 0.063(2) 0.0428(15) 0.0592(18) 0.0085(14) 0.0200(16) 0.0052(14) C4 0.063(2) 0.0415(15) 0.0538(17) 0.0048(13) 0.0191(15) 0.0059(14) C5 0.071(2) 0.0467(16) 0.0597(19) 0.0053(14) 0.0219(17) 0.0018(16) C6 0.067(2) 0.0595(19) 0.065(2) 0.0079(17) 0.0223(18) -0.0012(16) C7 0.073(2) 0.075(2) 0.077(2) 0.0124(19) 0.0381(19) 0.0115(19) C8 0.082(3) 0.0531(18) 0.073(2) -0.0029(16) 0.0345(19) 0.0031(18) C9 0.066(2) 0.0497(17) 0.0620(19) 0.0077(15) 0.0254(17) 0.0039(15) C10 0.066(2) 0.0466(17) 0.0637(19) 0.0067(14) 0.0238(16) 0.0079(15) C11 0.070(2) 0.0500(17) 0.076(2) 0.0125(16) 0.0225(18) -0.0034(16) C12 0.068(2) 0.0580(19) 0.074(2) 0.0173(17) 0.0291(18) 0.0174(17) C13 0.074(2) 0.064(2) 0.088(3) 0.0129(19) 0.030(2) 0.0109(18) C14 0.085(3) 0.110(3) 0.095(3) 0.020(3) 0.014(2) 0.004(2) C15 0.067(2) 0.0466(18) 0.087(3) 0.0014(18) 0.031(2) 0.0034(16) N1 0.075(2) 0.0490(15) 0.0759(19) -0.0048(13) 0.0300(16) -0.0025(14) O1 0.105(2) 0.0735(19) 0.146(3) 0.0130(19) 0.015(2) -0.0122(17) O2 0.162(3) 0.0673(17) 0.090(2) 0.0164(16) 0.021(2) -0.0187(18) C16 0.095(3) 0.107(3) 0.098(3) 0.029(3) 0.038(3) -0.012(3) C17 0.078(3) 0.107(3) 0.099(3) 0.034(3) 0.034(2) 0.006(2) C18 0.063(2) 0.0577(18) 0.062(2) -0.0005(15) 0.0212(17) -0.0055(16) C19 0.094(3) 0.109(3) 0.117(3) 0.052(3) 0.056(3) 0.032(3) C20 0.114(4) 0.113(4) 0.127(4) 0.047(3) 0.060(3) 0.044(3) C21 0.097(3) 0.100(3) 0.109(3) 0.032(3) 0.043(3) 0.032(3) C22 0.088(3) 0.099(3) 0.107(3) 0.035(3) 0.049(2) 0.018(2) C23 0.060(2) 0.0559(17) 0.0600(19) -0.0002(15) 0.0170(16) -0.0064(16) C24 0.076(2) 0.079(2) 0.080(2) 0.014(2) 0.029(2) 0.0075(19) C25 0.086(3) 0.077(2) 0.076(2) 0.011(2) 0.030(2) -0.004(2) N2 0.102(3) 0.0669(19) 0.079(2) 0.0106(16) 0.027(2) -0.0001(19) N3 0.086(2) 0.0618(17) 0.0725(19) 0.0038(15) 0.0177(17) -0.0018(17) C26 0.093(3) 0.091(3) 0.124(4) 0.046(3) 0.048(3) 0.013(3) C27 0.080(3) 0.079(3) 0.122(3) 0.041(2) 0.043(3) 0.023(2) C28 0.070(2) 0.0514(17) 0.0546(18) 0.0018(14) 0.0157(16) 0.0028(16) C29 0.082(3) 0.066(2) 0.085(3) 0.0250(19) 0.030(2) 0.0127(19) C30 0.078(3) 0.077(2) 0.093(3) 0.019(2) 0.030(2) 0.016(2) N4 0.082(2) 0.079(2) 0.088(2) 0.0082(18) 0.0312(18) 0.0025(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl1 C6 1.748(3) . ? C1 C2 1.365(4) . ? C1 C12 1.388(5) . ? C1 H1 0.9300 . ? C2 C3 1.401(4) . ? C2 H2 0.9300 . ? C3 C10 1.398(4) . ? C3 C4 1.433(4) . ? C4 C5 1.394(4) . ? C4 C9 1.412(4) . ? C5 C6 1.373(4) . ? C5 H5 0.9300 . ? C6 C7 1.393(5) . ? C7 C8 1.366(5) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 N1 1.376(4) . ? C10 N1 1.392(4) . ? C10 C11 1.396(5) . ? C11 C12 1.386(5) . ? C11 H11 0.9300 . ? C12 C13 1.520(5) . ? C13 C14 1.509(5) . ? C13 C15 1.512(5) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O1 1.198(4) . ? C15 O2 1.281(4) . ? N1 H1N 0.958(10) . ? O2 H2O 0.963(10) . ? C16 N2 1.310(5) . ? C16 C17 1.389(6) . ? C16 H16 0.9300 . ? C17 C18 1.359(5) . ? C17 H17 0.9300 . ? C18 C19 1.359(5) . ? C18 C23 1.486(4) . ? C19 C20 1.374(6) . ? C19 H19 0.9300 . ? C20 N2 1.317(5) . ? C20 H20 0.9300 . ? C21 N3 1.305(5) . ? C21 C22 1.377(5) . ? C21 H21 0.9300 . ? C22 C23 1.373(5) . ? C22 H22 0.9300 . ? C23 C24 1.368(5) . ? C24 C25 1.384(5) . ? C24 H24 0.9300 . ? C25 N3 1.312(5) . ? C25 H25 0.9300 . ? C26 N4 1.320(5) . ? C26 C27 1.371(6) . ? C26 H26 0.9300 . ? C27 C28 1.380(5) . ? C27 H27 0.9300 . ? C28 C29 1.382(4) . ? C28 C28 1.476(6) 3 ? C29 C30 1.371(5) . ? C29 H29 0.9300 . ? C30 N4 1.310(5) . ? C30 H30 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C12 121.8(3) . . ? C2 C1 H1 119.1 . . ? C12 C1 H1 119.1 . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C10 C3 C2 118.4(3) . . ? C10 C3 C4 107.5(3) . . ? C2 C3 C4 134.1(3) . . ? C5 C4 C9 119.2(3) . . ? C5 C4 C3 134.5(3) . . ? C9 C4 C3 106.4(3) . . ? C6 C5 C4 118.4(3) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C7 121.9(3) . . ? C5 C6 Cl1 119.6(3) . . ? C7 C6 Cl1 118.4(3) . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 118.7(3) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? N1 C9 C8 129.8(3) . . ? N1 C9 C4 109.0(3) . . ? C8 C9 C4 121.3(3) . . ? N1 C10 C11 129.7(3) . . ? N1 C10 C3 108.5(3) . . ? C11 C10 C3 121.8(3) . . ? C12 C11 C10 118.3(3) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C1 120.0(3) . . ? C11 C12 C13 120.8(3) . . ? C1 C12 C13 119.2(3) . . ? C14 C13 C15 112.7(3) . . ? C14 C13 C12 112.2(3) . . ? C15 C13 C12 111.8(3) . . ? C14 C13 H13 106.6 . . ? C15 C13 H13 106.6 . . ? C12 C13 H13 106.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 O2 122.1(3) . . ? O1 C15 C13 124.6(4) . . ? O2 C15 C13 113.3(3) . . ? C9 N1 C10 108.7(3) . . ? C9 N1 H1N 125(2) . . ? C10 N1 H1N 126(2) . . ? C15 O2 H2O 110(3) . . ? N2 C16 C17 124.3(4) . . ? N2 C16 H16 117.8 . . ? C17 C16 H16 117.8 . . ? C18 C17 C16 119.7(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 116.1(3) . . ? C17 C18 C23 121.2(3) . . ? C19 C18 C23 122.8(3) . . ? C18 C19 C20 120.4(4) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? N2 C20 C19 124.2(4) . . ? N2 C20 H20 117.9 . . ? C19 C20 H20 117.9 . . ? N3 C21 C22 124.2(4) . . ? N3 C21 H21 117.9 . . ? C22 C21 H21 117.9 . . ? C23 C22 C21 120.2(4) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 115.6(3) . . ? C24 C23 C18 122.4(3) . . ? C22 C23 C18 122.1(3) . . ? C23 C24 C25 120.0(4) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? N3 C25 C24 124.1(4) . . ? N3 C25 H25 117.9 . . ? C24 C25 H25 117.9 . . ? C16 N2 C20 115.2(4) . . ? C21 N3 C25 115.8(3) . . ? N4 C26 C27 125.4(4) . . ? N4 C26 H26 117.3 . . ? C27 C26 H26 117.3 . . ? C26 C27 C28 120.0(4) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C29 114.5(3) . . ? C27 C28 C28 122.1(4) . 3 ? C29 C28 C28 123.4(4) . 3 ? C30 C29 C28 121.1(3) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? N4 C30 C29 124.4(4) . . ? N4 C30 H30 117.8 . . ? C29 C30 H30 117.8 . . ? C30 N4 C26 114.7(3) . . ? 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 C12 C1 C2 C3 -0.5(5) . . . . ? C1 C2 C3 C10 0.4(4) . . . . ? C1 C2 C3 C4 -178.1(3) . . . . ? C10 C3 C4 C5 179.5(3) . . . . ? C2 C3 C4 C5 -1.8(6) . . . . ? C10 C3 C4 C9 -0.4(3) . . . . ? C2 C3 C4 C9 178.3(3) . . . . ? C9 C4 C5 C6 -0.3(4) . . . . ? C3 C4 C5 C6 179.8(3) . . . . ? C4 C5 C6 C7 0.0(5) . . . . ? C4 C5 C6 Cl1 177.9(2) . . . . ? C5 C6 C7 C8 -0.3(5) . . . . ? Cl1 C6 C7 C8 -178.3(3) . . . . ? C6 C7 C8 C9 1.0(5) . . . . ? C7 C8 C9 N1 178.8(3) . . . . ? C7 C8 C9 C4 -1.3(5) . . . . ? C5 C4 C9 N1 -179.1(3) . . . . ? C3 C4 C9 N1 0.8(3) . . . . ? C5 C4 C9 C8 0.9(4) . . . . ? C3 C4 C9 C8 -179.1(3) . . . . ? C2 C3 C10 N1 -179.1(3) . . . . ? C4 C3 C10 N1 -0.2(3) . . . . ? C2 C3 C10 C11 -0.1(4) . . . . ? C4 C3 C10 C11 178.8(3) . . . . ? N1 C10 C11 C12 178.6(3) . . . . ? C3 C10 C11 C12 -0.2(5) . . . . ? C10 C11 C12 C1 0.1(5) . . . . ? C10 C11 C12 C13 -177.4(3) . . . . ? C2 C1 C12 C11 0.2(5) . . . . ? C2 C1 C12 C13 177.8(3) . . . . ? C11 C12 C13 C14 66.9(4) . . . . ? C1 C12 C13 C14 -110.6(4) . . . . ? C11 C12 C13 C15 -60.8(4) . . . . ? C1 C12 C13 C15 121.7(4) . . . . ? C14 C13 C15 O1 -15.9(5) . . . . ? C12 C13 C15 O1 111.6(4) . . . . ? C14 C13 C15 O2 166.2(4) . . . . ? C12 C13 C15 O2 -66.4(4) . . . . ? C8 C9 N1 C10 179.0(3) . . . . ? C4 C9 N1 C10 -0.9(3) . . . . ? C11 C10 N1 C9 -178.2(3) . . . . ? C3 C10 N1 C9 0.7(3) . . . . ? N2 C16 C17 C18 1.2(7) . . . . ? C16 C17 C18 C19 -3.1(6) . . . . ? C16 C17 C18 C23 177.5(4) . . . . ? C17 C18 C19 C20 3.0(7) . . . . ? C23 C18 C19 C20 -177.6(4) . . . . ? C18 C19 C20 N2 -1.1(8) . . . . ? N3 C21 C22 C23 0.3(7) . . . . ? C21 C22 C23 C24 0.2(6) . . . . ? C21 C22 C23 C18 -179.4(4) . . . . ? C17 C18 C23 C24 -167.2(4) . . . . ? C19 C18 C23 C24 13.5(5) . . . . ? C17 C18 C23 C22 12.4(5) . . . . ? C19 C18 C23 C22 -166.9(4) . . . . ? C22 C23 C24 C25 -0.7(5) . . . . ? C18 C23 C24 C25 179.0(3) . . . . ? C23 C24 C25 N3 0.7(6) . . . . ? C17 C16 N2 C20 0.8(7) . . . . ? C19 C20 N2 C16 -0.9(7) . . . . ? C22 C21 N3 C25 -0.3(7) . . . . ? C24 C25 N3 C21 -0.1(6) . . . . ? N4 C26 C27 C28 -1.0(8) . . . . ? C26 C27 C28 C29 1.3(6) . . . . ? C26 C27 C28 C28 -179.1(4) . . . 3 ? C27 C28 C29 C30 -0.3(5) . . . . ? C28 C28 C29 C30 -179.9(4) 3 . . . ? C28 C29 C30 N4 -1.2(7) . . . . ? C29 C30 N4 C26 1.4(6) . . . . ? C27 C26 N4 C30 -0.3(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.394 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.044