# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_lgl17 #TrackingRef 'lgl17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H30 Cd N5 O6' _chemical_formula_weight 777.08 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' Cd Cd -0.8075 1.2024 '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 20.048(4) _cell_length_b 12.245(2) _cell_length_c 29.217(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.84(3) _cell_angle_gamma 90.00 _cell_volume 6788(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3160 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7528 _exptl_absorpt_correction_T_max 0.8444 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21737 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5882 _reflns_number_gt 4810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+403.9642P] 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 5882 _refine_ls_number_parameters 460 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.1142 _refine_ls_wR_factor_ref 0.2390 _refine_ls_wR_factor_gt 0.2314 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.184 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1957(6) 0.4419(9) 0.1497(4) 0.021(2) Uani 1 1 d . . . C2 C 0.2112(6) 0.5508(10) 0.1370(4) 0.026(3) Uani 1 1 d . . . H2 H 0.2399 0.5951 0.1613 0.031 Uiso 1 1 calc R . . C3 C 0.1871(6) 0.5904(9) 0.0932(4) 0.020(2) Uani 1 1 d . . . H3 H 0.1631 0.5412 0.0693 0.024 Uiso 1 1 calc R . . C4 C 0.1929(6) 0.7020(10) 0.0769(4) 0.024(3) Uani 1 1 d . . . C5 C 0.2207(7) 0.7847(10) 0.1091(5) 0.034(3) Uani 1 1 d . . . H5 H 0.2379 0.7701 0.1421 0.041 Uiso 1 1 calc R . . C6 C 0.2230(7) 0.8915(11) 0.0921(5) 0.032(3) Uani 1 1 d . . . H6 H 0.2399 0.9463 0.1149 0.038 Uiso 1 1 calc R . . C7 C 0.1757(6) 0.8389(10) 0.0132(4) 0.024(3) Uani 1 1 d U . . C8 C 0.1542(8) 0.8700(12) -0.0351(5) 0.044(4) Uani 1 1 d . . . H8 H 0.1564 0.9429 -0.0434 0.053 Uiso 1 1 calc R . . C9 C 0.1295(9) 0.7913(13) -0.0708(5) 0.048(4) Uani 1 1 d . . . H9 H 0.1191 0.8097 -0.1032 0.058 Uiso 1 1 calc R . . C10 C 0.1202(8) 0.6845(12) -0.0574(5) 0.040(3) Uani 1 1 d U . . H10 H 0.0993 0.6339 -0.0815 0.048 Uiso 1 1 calc R . . C11 C 0.1408(7) 0.6516(11) -0.0104(5) 0.036(3) Uani 1 1 d . . . H11 H 0.1358 0.5789 -0.0028 0.043 Uiso 1 1 calc R . . C12 C 0.1695(6) 0.7278(9) 0.0266(4) 0.021(2) Uani 1 1 d . . . C13 C 0.1334(5) 0.1420(9) 0.2587(4) 0.016(2) Uani 1 1 d U . . C14 C 0.1177(6) 0.0933(11) 0.2951(4) 0.029(3) Uani 1 1 d U . . H14 H 0.1320 0.1253 0.3256 0.035 Uiso 1 1 calc R . . C15 C 0.0771(14) -0.012(2) 0.2871(10) 0.107(9) Uani 1 1 d . . . C16 C 0.0596(11) -0.078(2) 0.3269(8) 0.107(9) Uani 1 1 d DU . . C17 C 0.1080(10) -0.0965(13) 0.3708(5) 0.059(5) Uani 1 1 d DU . . H17 H 0.1503 -0.0588 0.3776 0.070 Uiso 1 1 calc R . . C18 C 0.1013(8) -0.1644(12) 0.4063(5) 0.050(4) Uani 1 1 d DU . . H18 H 0.1375 -0.1767 0.4352 0.060 Uiso 1 1 calc R . . C19 C -0.0136(10) -0.1977(17) 0.3517(7) 0.081(5) Uani 1 1 d DU . . C20 C -0.0786(9) -0.249(2) 0.3411(9) 0.109(9) Uani 1 1 d D . . H20 H -0.0855 -0.2926 0.3653 0.131 Uiso 1 1 calc R . . C21 C -0.1327(11) -0.243(2) 0.2992(8) 0.114(12) Uani 1 1 d D . . H21 H -0.1753 -0.2788 0.2942 0.137 Uiso 1 1 calc R . . C22 C -0.1199(11) -0.1784(19) 0.2646(10) 0.145(15) Uani 1 1 d D . . H22 H -0.1555 -0.1729 0.2349 0.174 Uiso 1 1 calc R . . C23 C -0.0585(10) -0.121(2) 0.2701(8) 0.122(11) Uani 1 1 d D . . C24 C -0.0040(9) -0.1356(16) 0.3140(7) 0.080(6) Uani 1 1 d D . . C25 C 0.2851(6) 0.1775(10) 0.1535(5) 0.028(3) Uani 1 1 d . . . H25 H 0.2707 0.2373 0.1330 0.033 Uiso 1 1 calc R . . C26 C 0.3459(6) 0.1231(9) 0.1544(5) 0.026(3) Uani 1 1 d . . . H26 H 0.3726 0.1467 0.1356 0.031 Uiso 1 1 calc R . . C27 C 0.2646(5) 0.0591(9) 0.2085(4) 0.018(2) Uani 1 1 d . . . H27 H 0.2368 0.0363 0.2268 0.022 Uiso 1 1 calc R . . C28 C 0.0721(8) 0.0469(11) 0.1078(5) 0.040(4) Uani 1 1 d . . . H28 H 0.0860 0.0123 0.1378 0.048 Uiso 1 1 calc R . . C29 C 0.0430(8) -0.0165(10) 0.0668(4) 0.037(3) Uani 1 1 d . . . H29 H 0.0407 -0.0920 0.0695 0.044 Uiso 1 1 calc R . . C30 C 0.0175(6) 0.0325(9) 0.0221(4) 0.021(2) Uani 1 1 d . . . C31 C 0.0246(8) 0.1433(11) 0.0208(4) 0.040(4) Uani 1 1 d . . . H31 H 0.0096 0.1806 -0.0085 0.048 Uiso 1 1 calc R . . C32 C 0.0543(8) 0.1991(11) 0.0635(5) 0.047(4) Uani 1 1 d . . . H32 H 0.0556 0.2749 0.0620 0.056 Uiso 1 1 calc R . . C33 C -0.0087(5) 0.3009(9) 0.1861(4) 0.017(2) Uani 1 1 d . . . H33 H -0.0081 0.2250 0.1876 0.021 Uiso 1 1 calc R . . C34 C -0.0675(6) 0.3549(9) 0.1881(4) 0.022(2) Uani 1 1 d . . . H34 H -0.1055 0.3166 0.1919 0.027 Uiso 1 1 calc R . . C35 C -0.0692(6) 0.4694(9) 0.1845(4) 0.019(2) Uani 1 1 d . . . C36 C -0.0100(6) 0.5217(10) 0.1800(5) 0.029(3) Uani 1 1 d . . . H36 H -0.0089 0.5974 0.1781 0.035 Uiso 1 1 calc R . . C37 C 0.0466(6) 0.4612(10) 0.1784(5) 0.027(3) Uani 1 1 d . . . H37 H 0.0852 0.4974 0.1746 0.033 Uiso 1 1 calc R . . C38 C -0.1334(6) 0.5309(10) 0.1848(4) 0.024(3) Uani 1 1 d . . . C39 C -0.1755(6) 0.4991(9) 0.2109(4) 0.022(2) Uani 1 1 d . . . H39 H -0.1641 0.4373 0.2304 0.026 Uiso 1 1 calc R . . Cd1 Cd 0.14573(4) 0.24911(8) 0.17651(3) 0.0192(2) Uani 1 1 d . . . N1 N 0.2034(6) 0.9193(9) 0.0469(4) 0.039(3) Uani 1 1 d . . . N2 N 0.0362(9) -0.2126(15) 0.3954(6) 0.093(5) Uani 1 1 d DU . . N3 N 0.2454(5) 0.1469(7) 0.1813(3) 0.019(2) Uani 1 1 d . . . N4 N 0.0811(5) 0.1529(8) 0.1067(3) 0.020(2) Uani 1 1 d . . . N5 N 0.0487(5) 0.3530(8) 0.1819(3) 0.023(2) Uani 1 1 d . . . O1 O 0.2118(4) 0.4152(6) 0.1943(3) 0.0239(18) Uani 1 1 d . . . O2 O 0.1638(4) 0.3740(6) 0.1173(3) 0.0245(18) Uani 1 1 d . . . O3 O 0.1024(4) 0.1088(6) 0.2153(3) 0.0249(18) Uani 1 1 d . . . O4 O 0.1754(4) 0.2183(6) 0.2661(3) 0.0267(19) Uani 1 1 d . . . O5 O 0.2184(12) 0.1262(12) 0.0117(8) 0.167(11) Uani 1 1 d . . . H5A H 0.2173 0.0607 0.0211 0.201 Uiso 1 1 d R . . H5B H 0.2507 0.1316 -0.0011 0.201 Uiso 1 1 d R . . O6 O 0.1857(11) 0.3344(13) 0.0283(6) 0.119(6) Uani 1 1 d . . . H6B H 0.1799 0.3133 0.0545 0.142 Uiso 1 1 d R . . H6A H 0.1530 0.3095 0.0041 0.142 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.014(5) 0.022(6) 0.029(6) -0.007(5) 0.008(5) 0.000(5) C2 0.019(6) 0.028(6) 0.033(7) -0.002(5) 0.010(5) 0.001(5) C3 0.019(6) 0.022(6) 0.021(6) -0.006(5) 0.010(5) -0.009(5) C4 0.013(6) 0.027(6) 0.030(6) 0.005(5) 0.005(5) -0.004(5) C5 0.042(8) 0.029(7) 0.027(6) 0.002(5) 0.006(6) -0.018(6) C6 0.026(7) 0.035(7) 0.033(7) -0.006(6) 0.008(6) -0.003(6) C7 0.011(5) 0.040(7) 0.027(6) 0.005(5) 0.014(5) 0.000(5) C8 0.053(9) 0.036(8) 0.042(8) 0.015(7) 0.013(7) -0.009(7) C9 0.065(10) 0.064(10) 0.022(7) 0.010(7) 0.020(7) -0.006(8) C10 0.051(7) 0.045(7) 0.030(6) 0.001(5) 0.021(5) -0.016(6) C11 0.040(8) 0.032(7) 0.029(7) -0.004(6) 0.001(6) 0.002(6) C12 0.024(6) 0.019(6) 0.024(6) 0.004(4) 0.011(5) 0.005(5) C13 0.007(4) 0.022(5) 0.017(5) 0.000(4) 0.001(4) 0.002(4) C14 0.020(5) 0.051(7) 0.020(5) -0.006(5) 0.013(4) -0.014(5) C15 0.13(2) 0.098(18) 0.12(2) 0.053(16) 0.080(18) 0.063(17) C16 0.095(18) 0.098(18) 0.088(15) 0.019(14) -0.025(11) -0.033(15) C17 0.084(13) 0.039(9) 0.046(8) 0.003(7) 0.012(7) 0.001(9) C18 0.048(8) 0.052(9) 0.053(8) -0.016(7) 0.019(7) -0.009(7) C19 0.085(9) 0.081(9) 0.083(8) 0.004(7) 0.036(7) 0.002(7) C20 0.058(12) 0.093(17) 0.17(3) -0.070(19) 0.030(15) -0.018(14) C21 0.095(18) 0.13(2) 0.15(2) -0.10(2) 0.086(18) -0.087(18) C22 0.041(13) 0.11(2) 0.25(4) -0.10(3) -0.002(19) -0.005(13) C23 0.071(15) 0.12(2) 0.12(2) -0.015(17) -0.052(14) 0.019(15) C24 0.062(13) 0.069(13) 0.111(18) 0.009(12) 0.031(12) 0.006(11) C25 0.016(6) 0.020(6) 0.046(7) 0.005(5) 0.009(5) 0.007(5) C26 0.019(6) 0.017(6) 0.047(7) 0.012(5) 0.018(5) 0.009(5) C27 0.008(5) 0.023(6) 0.026(6) 0.006(5) 0.008(4) 0.002(4) C28 0.069(10) 0.028(7) 0.023(6) -0.002(5) 0.014(7) -0.022(7) C29 0.074(10) 0.013(6) 0.019(6) -0.001(5) 0.008(6) -0.009(6) C30 0.014(5) 0.018(6) 0.029(6) 0.001(5) 0.005(5) -0.004(4) C31 0.054(9) 0.030(7) 0.017(6) 0.002(5) -0.013(6) -0.014(6) C32 0.074(11) 0.022(7) 0.025(7) 0.005(6) -0.011(7) -0.003(7) C33 0.011(5) 0.017(5) 0.021(5) 0.001(4) -0.001(4) 0.003(4) C34 0.018(6) 0.024(6) 0.024(6) 0.002(5) 0.005(5) -0.006(5) C35 0.016(6) 0.020(6) 0.023(6) 0.002(5) 0.010(5) 0.009(5) C36 0.018(6) 0.016(6) 0.053(8) 0.000(5) 0.010(6) 0.009(5) C37 0.014(6) 0.022(6) 0.046(7) -0.004(5) 0.010(5) 0.002(5) C38 0.015(6) 0.027(6) 0.025(6) 0.001(5) -0.002(5) 0.008(5) C39 0.023(6) 0.020(6) 0.021(6) 0.004(5) 0.004(5) 0.009(5) Cd1 0.0202(4) 0.0173(4) 0.0192(4) -0.0013(4) 0.0051(3) 0.0026(4) N1 0.048(7) 0.034(6) 0.035(6) 0.004(5) 0.014(5) -0.005(5) N2 0.093(5) 0.093(5) 0.093(5) -0.0002(10) 0.0297(18) 0.0001(10) N3 0.012(4) 0.022(5) 0.022(5) -0.002(4) 0.004(4) 0.006(4) N4 0.014(5) 0.026(5) 0.020(5) 0.000(4) 0.004(4) 0.004(4) N5 0.025(5) 0.021(5) 0.023(5) 0.002(4) 0.006(4) 0.007(4) O1 0.023(4) 0.024(4) 0.024(4) 0.006(3) 0.007(3) 0.004(3) O2 0.025(4) 0.021(4) 0.023(4) 0.000(3) 0.002(3) -0.014(3) O3 0.017(4) 0.025(4) 0.029(4) 0.001(4) 0.003(3) -0.001(3) O4 0.025(4) 0.025(5) 0.033(4) -0.003(3) 0.014(4) -0.001(3) O5 0.26(3) 0.043(9) 0.31(3) 0.041(13) 0.24(2) 0.023(12) O6 0.194(19) 0.086(11) 0.106(13) -0.014(10) 0.090(13) 0.007(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.268(13) . ? C1 O1 1.278(13) . ? C1 C2 1.445(17) . ? C2 C3 1.307(16) . ? C3 C4 1.465(16) . ? C4 C5 1.373(16) . ? C4 C12 1.425(15) . ? C5 C6 1.407(18) . ? C6 N1 1.295(16) . ? C7 N1 1.375(16) . ? C7 C8 1.389(17) . ? C7 C12 1.432(16) . ? C8 C9 1.39(2) . ? C9 C10 1.39(2) . ? C10 C11 1.363(18) . ? C11 C12 1.403(17) . ? C13 O4 1.229(13) . ? C13 O3 1.285(13) . ? C13 C14 1.343(15) . ? C14 C15 1.50(3) . ? C15 C16 1.55(3) . ? C16 C17 1.354(16) . ? C16 C24 1.397(17) . ? C17 C18 1.370(15) . ? C18 N2 1.374(15) . ? C19 N2 1.355(16) . ? C19 C20 1.390(17) . ? C19 C24 1.401(16) . ? C20 C21 1.351(18) . ? C21 C22 1.368(10) . ? C22 C23 1.382(18) . ? C23 C24 1.401(17) . ? C25 N3 1.359(15) . ? C25 C26 1.382(15) . ? C26 C38 1.413(16) 3_545 ? C27 N3 1.319(14) . ? C27 C39 1.391(15) 3_545 ? C28 N4 1.313(16) . ? C28 C29 1.389(17) . ? C29 C30 1.377(16) . ? C30 C31 1.366(17) . ? C30 C30 1.49(2) 5 ? C31 C32 1.378(17) . ? C32 N4 1.328(15) . ? C33 C34 1.370(15) . ? C33 N5 1.354(14) . ? C34 C35 1.406(16) . ? C35 C36 1.391(16) . ? C35 C38 1.494(14) . ? C36 C37 1.369(16) . ? C37 N5 1.328(15) . ? C38 C39 1.364(16) . ? C38 C26 1.413(16) 3_455 ? C39 C27 1.391(15) 3_455 ? Cd1 N3 2.324(9) . ? Cd1 N4 2.350(9) . ? Cd1 N5 2.372(9) . ? Cd1 O3 2.372(8) . ? Cd1 O1 2.392(8) . ? Cd1 O2 2.422(8) . ? Cd1 O4 2.519(8) . ? 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 O2 C1 O1 119.6(10) . . ? O2 C1 C2 120.8(11) . . ? O1 C1 C2 119.6(10) . . ? C3 C2 C1 123.5(11) . . ? C2 C3 C4 128.5(11) . . ? C5 C4 C12 118.0(11) . . ? C5 C4 C3 121.4(10) . . ? C12 C4 C3 120.6(10) . . ? C4 C5 C6 119.7(11) . . ? N1 C6 C5 124.9(12) . . ? N1 C7 C8 116.8(12) . . ? N1 C7 C12 122.4(10) . . ? C8 C7 C12 120.8(12) . . ? C9 C8 C7 119.4(13) . . ? C8 C9 C10 119.2(12) . . ? C11 C10 C9 122.4(14) . . ? C10 C11 C12 119.7(13) . . ? C11 C12 C4 124.2(11) . . ? C11 C12 C7 118.2(11) . . ? C4 C12 C7 117.6(10) . . ? O4 C13 O3 120.1(10) . . ? O4 C13 C14 121.3(10) . . ? O3 C13 C14 118.6(10) . . ? C13 C14 C15 120.9(14) . . ? C14 C15 C16 125(2) . . ? C17 C16 C24 119.0(19) . . ? C17 C16 C15 122(2) . . ? C24 C16 C15 118.1(18) . . ? C16 C17 C18 127.1(18) . . ? C17 C18 N2 113.7(16) . . ? N2 C19 C20 120.0(18) . . ? N2 C19 C24 124.5(17) . . ? C20 C19 C24 115.4(19) . . ? C21 C20 C19 127(2) . . ? C20 C21 C22 115(2) . . ? C21 C22 C23 125(2) . . ? C22 C23 C24 116(2) . . ? C19 C24 C16 114.0(17) . . ? C19 C24 C23 121.6(19) . . ? C16 C24 C23 123.8(18) . . ? N3 C25 C26 122.5(11) . . ? C25 C26 C38 118.4(11) . 3_545 ? N3 C27 C39 122.6(10) . 3_545 ? N4 C28 C29 123.6(12) . . ? C30 C29 C28 119.9(11) . . ? C31 C30 C29 116.7(11) . . ? C31 C30 C30 122.2(13) . 5 ? C29 C30 C30 121.1(13) . 5 ? C30 C31 C32 119.0(12) . . ? N4 C32 C31 125.0(12) . . ? C34 C33 N5 123.0(10) . . ? C33 C34 C35 118.6(11) . . ? C36 C35 C34 117.7(10) . . ? C36 C35 C38 122.1(10) . . ? C34 C35 C38 120.2(10) . . ? C37 C36 C35 119.7(11) . . ? N5 C37 C36 122.9(12) . . ? C39 C38 C26 118.1(10) . 3_455 ? C39 C38 C35 123.3(10) . . ? C26 C38 C35 118.5(10) 3_455 . ? C38 C39 C27 120.1(10) . 3_455 ? N3 Cd1 N4 90.2(3) . . ? N3 Cd1 N5 173.1(3) . . ? N4 Cd1 N5 95.3(3) . . ? N3 Cd1 O3 91.3(3) . . ? N4 Cd1 O3 82.4(3) . . ? N5 Cd1 O3 85.5(3) . . ? N3 Cd1 O1 92.2(3) . . ? N4 Cd1 O1 136.6(3) . . ? N5 Cd1 O1 86.5(3) . . ? O3 Cd1 O1 140.8(3) . . ? N3 Cd1 O2 93.3(3) . . ? N4 Cd1 O2 82.2(3) . . ? N5 Cd1 O2 91.4(3) . . ? O3 Cd1 O2 163.9(2) . . ? O1 Cd1 O2 54.4(2) . . ? N3 Cd1 O4 87.0(3) . . ? N4 Cd1 O4 134.9(3) . . ? N5 Cd1 O4 86.2(3) . . ? O3 Cd1 O4 52.8(3) . . ? O1 Cd1 O4 88.5(3) . . ? O2 Cd1 O4 142.9(3) . . ? C6 N1 C7 117.4(11) . . ? C19 N2 C18 121.1(17) . . ? C27 N3 C25 118.3(9) . . ? C27 N3 Cd1 123.5(7) . . ? C25 N3 Cd1 118.2(7) . . ? C28 N4 C32 115.4(11) . . ? C28 N4 Cd1 121.0(8) . . ? C32 N4 Cd1 123.5(8) . . ? C37 N5 C33 118.0(10) . . ? C37 N5 Cd1 122.4(8) . . ? C33 N5 Cd1 119.5(7) . . ? C1 O1 Cd1 93.2(7) . . ? C1 O2 Cd1 92.1(7) . . ? C13 O3 Cd1 96.1(6) . . ? C13 O4 Cd1 90.7(6) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.514 _refine_diff_density_min -0.846 _refine_diff_density_rms 0.159 _database_code_depnum_ccdc_archive 'CCDC 867075' ####################################################################### # # 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_lgl18 #TrackingRef 'lgl18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Cd N2 O5' _chemical_formula_weight 526.80 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' Cd Cd -0.8075 1.2024 '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 15.5371(6) _cell_length_b 15.4888(6) _cell_length_c 9.0606(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.8770(10) _cell_angle_gamma 90.00 _cell_volume 2177.69(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.041 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6459 _exptl_absorpt_correction_T_max 0.7384 _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 29055 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5277 _reflns_number_gt 4397 _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^)+(0.0223P)^2^+0.9222P] 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 5277 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0554 _refine_ls_wR_factor_gt 0.0506 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Cd1 Cd 0.284619(9) 0.205542(8) 0.431667(14) 0.03037(5) Uani 1 1 d . . . O5 O 0.16066(11) 0.26186(11) 0.3364(2) 0.0463(4) Uani 1 1 d . . . O3 O 0.34561(10) 0.33752(9) 0.45974(15) 0.0449(4) Uani 1 1 d . . . N2 N 0.41476(11) 0.14769(10) 0.54511(18) 0.0364(4) Uani 1 1 d . . . C23 C 0.34694(12) 0.35594(12) 0.5951(2) 0.0326(4) Uani 1 1 d . . . O1 O 0.20692(10) 0.05580(10) 0.41105(16) 0.0478(4) Uani 1 1 d . . . C15 C 0.54564(13) 0.04366(12) 0.6830(2) 0.0340(4) Uani 1 1 d . . . O2 O 0.20478(9) 0.14101(9) 0.60430(16) 0.0449(4) Uani 1 1 d . . . O4 O 0.30691(9) 0.18655(9) 0.18633(15) 0.0407(3) Uani 1 1 d . . . C17 C 0.56511(12) 0.09927(12) 0.5634(2) 0.0341(4) Uani 1 1 d . . . C22 C 0.49760(13) 0.15053(12) 0.4976(2) 0.0363(4) Uani 1 1 d . . . C4 C 0.06757(14) -0.05293(13) 0.8366(2) 0.0414(5) Uani 1 1 d . . . C1 C 0.18254(13) 0.07285(13) 0.5358(2) 0.0372(4) Uani 1 1 d . . . C24 C 0.40327(14) 0.42934(14) 0.6431(2) 0.0432(5) Uani 1 1 d . . . H24 H 0.4507 0.4407 0.5876 0.052 Uiso 1 1 calc R . . C16 C 0.60825(13) -0.02045(12) 0.7428(2) 0.0353(4) Uani 1 1 d . . . H16 H 0.6599 -0.0257 0.6962 0.042 Uiso 1 1 calc R . . C21 C 0.51502(16) 0.20475(14) 0.3778(3) 0.0511(6) Uani 1 1 d . . . H21 H 0.4713 0.2388 0.3348 0.061 Uiso 1 1 calc R . . C20 C 0.59512(17) 0.20759(18) 0.3248(3) 0.0692(8) Uani 1 1 d . . . H20 H 0.6057 0.2435 0.2455 0.083 Uiso 1 1 calc R . . N1 N -0.04247(13) -0.15863(13) 0.9950(2) 0.0500(5) Uani 1 1 d . . . C3 C 0.12219(14) 0.00649(14) 0.7550(2) 0.0432(5) Uani 1 1 d . . . H3 H 0.1566 0.0448 0.8107 0.052 Uiso 1 1 calc R . . C5 C -0.01709(14) -0.06402(15) 0.7938(2) 0.0474(5) Uani 1 1 d . . . H5 H -0.0400 -0.0361 0.7098 0.057 Uiso 1 1 calc R . . C14 C 0.46382(14) 0.04760(14) 0.7314(2) 0.0417(5) Uani 1 1 d . . . H14 H 0.4497 0.0151 0.8131 0.050 Uiso 1 1 calc R . . C7 C 0.04253(15) -0.14967(14) 1.0410(2) 0.0465(5) Uani 1 1 d . . . C12 C 0.10042(14) -0.09741(13) 0.9647(2) 0.0418(5) Uani 1 1 d . . . C18 C 0.64770(14) 0.10477(14) 0.5047(3) 0.0465(5) Uani 1 1 d . . . H18 H 0.6928 0.0720 0.5465 0.056 Uiso 1 1 calc R . . C13 C 0.40115(14) 0.09951(13) 0.6606(2) 0.0403(5) Uani 1 1 d . . . H13 H 0.3464 0.1000 0.6975 0.048 Uiso 1 1 calc R . . C8 C 0.0727(2) -0.19360(18) 1.1707(3) 0.0700(8) Uani 1 1 d . . . H8 H 0.0351 -0.2281 1.2214 0.084 Uiso 1 1 calc R . . C6 C -0.06984(15) -0.11743(15) 0.8761(3) 0.0497(6) Uani 1 1 d . . . H6 H -0.1273 -0.1237 0.8442 0.060 Uiso 1 1 calc R . . C19 C 0.66200(16) 0.15722(18) 0.3881(3) 0.0652(7) Uani 1 1 d . . . H19 H 0.7165 0.1596 0.3502 0.078 Uiso 1 1 calc R . . C2 C 0.12649(14) 0.01005(14) 0.6112(2) 0.0431(5) Uani 1 1 d . . . H2 H 0.0932 -0.0282 0.5535 0.052 Uiso 1 1 calc R . . C11 C 0.18682(16) -0.09198(17) 1.0205(3) 0.0592(6) Uani 1 1 d . . . H11 H 0.2260 -0.0584 0.9716 0.071 Uiso 1 1 calc R . . C10 C 0.21329(19) -0.1355(2) 1.1456(4) 0.0787(9) Uani 1 1 d . . . H10 H 0.2704 -0.1316 1.1808 0.094 Uiso 1 1 calc R . . C9 C 0.1553(2) -0.1859(2) 1.2211(4) 0.0856(10) Uani 1 1 d . . . H9 H 0.1739 -0.2145 1.3072 0.103 Uiso 1 1 calc R . . H50 H 0.134(2) 0.2831(19) 0.386(4) 0.076(11) Uiso 1 1 d . . . H51 H 0.1639(17) 0.3000(17) 0.257(3) 0.067(8) Uiso 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 Cd1 0.03165(8) 0.03089(8) 0.02901(8) 0.00146(5) 0.00584(5) 0.00029(6) O5 0.0426(9) 0.0524(9) 0.0451(9) 0.0051(8) 0.0133(7) 0.0174(7) O3 0.0656(10) 0.0411(8) 0.0285(7) -0.0036(6) 0.0072(7) -0.0145(7) N2 0.0383(9) 0.0384(9) 0.0322(8) -0.0017(7) -0.0008(7) 0.0063(7) C23 0.0356(10) 0.0329(9) 0.0296(10) -0.0024(7) 0.0032(8) -0.0025(8) O1 0.0509(9) 0.0519(9) 0.0420(8) 0.0020(7) 0.0172(7) 0.0015(7) C15 0.0416(11) 0.0307(9) 0.0295(9) -0.0039(7) 0.0001(8) 0.0050(8) O2 0.0506(9) 0.0456(8) 0.0392(8) 0.0005(6) 0.0095(7) -0.0163(7) O4 0.0485(9) 0.0433(8) 0.0310(7) 0.0019(6) 0.0103(6) 0.0135(6) C17 0.0366(11) 0.0303(9) 0.0351(10) -0.0020(8) -0.0012(8) 0.0008(8) C22 0.0408(11) 0.0315(9) 0.0363(10) 0.0000(8) -0.0004(8) -0.0005(8) C4 0.0443(12) 0.0414(11) 0.0393(11) 0.0002(9) 0.0106(9) -0.0105(9) C1 0.0303(10) 0.0437(11) 0.0378(11) 0.0081(9) 0.0045(8) -0.0002(8) C24 0.0468(13) 0.0480(12) 0.0356(11) -0.0045(9) 0.0093(9) -0.0176(10) C16 0.0372(11) 0.0335(10) 0.0354(10) -0.0005(8) 0.0044(8) 0.0051(8) C21 0.0466(13) 0.0484(13) 0.0578(14) 0.0194(11) -0.0027(11) 0.0007(10) C20 0.0520(16) 0.0753(18) 0.081(2) 0.0443(15) 0.0080(14) -0.0042(13) N1 0.0517(12) 0.0533(11) 0.0461(11) 0.0010(9) 0.0116(9) -0.0186(9) C3 0.0428(12) 0.0433(11) 0.0440(12) 0.0020(9) 0.0072(10) -0.0103(9) C5 0.0467(13) 0.0558(13) 0.0397(12) 0.0061(10) 0.0032(10) -0.0096(10) C14 0.0475(12) 0.0486(12) 0.0295(10) 0.0069(9) 0.0061(9) 0.0119(9) C7 0.0517(14) 0.0455(12) 0.0429(12) 0.0018(10) 0.0081(10) -0.0124(10) C12 0.0426(12) 0.0412(11) 0.0422(11) 0.0005(9) 0.0079(9) -0.0101(9) C18 0.0379(12) 0.0449(12) 0.0566(14) 0.0109(10) 0.0002(10) 0.0016(9) C13 0.0415(12) 0.0482(12) 0.0316(10) -0.0018(9) 0.0068(9) 0.0089(9) C8 0.078(2) 0.0706(18) 0.0611(17) 0.0245(14) 0.0049(15) -0.0179(15) C6 0.0422(13) 0.0593(14) 0.0481(13) -0.0053(11) 0.0072(10) -0.0147(11) C19 0.0416(14) 0.0723(17) 0.0828(19) 0.0339(15) 0.0125(13) -0.0020(12) C2 0.0419(12) 0.0452(12) 0.0426(12) 0.0008(9) 0.0056(9) -0.0128(9) C11 0.0492(14) 0.0633(16) 0.0649(16) 0.0116(13) -0.0005(12) -0.0135(12) C10 0.0588(18) 0.092(2) 0.083(2) 0.0217(18) -0.0180(16) -0.0108(16) C9 0.088(2) 0.092(2) 0.074(2) 0.0341(18) -0.0189(18) -0.0128(19) _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 Cd1 O5 2.2469(16) . ? Cd1 O3 2.2621(14) . ? Cd1 O2 2.2758(13) . ? Cd1 O4 2.2858(13) . ? Cd1 N2 2.3957(16) . ? Cd1 O1 2.6170(15) . ? O3 C23 1.259(2) . ? N2 C13 1.311(3) . ? N2 C22 1.378(3) . ? C23 O4 1.247(2) 4_566 ? C23 C24 1.486(3) . ? O1 C1 1.238(2) . ? C15 C14 1.367(3) . ? C15 C17 1.428(3) . ? C15 C16 1.474(3) . ? O2 C1 1.264(2) . ? O4 C23 1.247(2) 4_565 ? C17 C18 1.416(3) . ? C17 C22 1.423(3) . ? C22 C21 1.409(3) . ? C4 C5 1.363(3) . ? C4 C12 1.423(3) . ? C4 C3 1.475(3) . ? C1 C2 1.494(3) . ? C24 C16 1.313(3) 2_656 ? C16 C24 1.313(3) 2_646 ? C21 C20 1.357(4) . ? C20 C19 1.399(4) . ? N1 C6 1.305(3) . ? N1 C7 1.372(3) . ? C3 C2 1.310(3) . ? C5 C6 1.405(3) . ? C14 C13 1.394(3) . ? C7 C12 1.415(3) . ? C7 C8 1.417(3) . ? C12 C11 1.413(3) . ? C18 C19 1.360(3) . ? C8 C9 1.345(4) . ? C11 C10 1.364(4) . ? C10 C9 1.398(4) . ? 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 O5 Cd1 O3 92.21(6) . . ? O5 Cd1 O2 87.03(6) . . ? O3 Cd1 O2 124.01(5) . . ? O5 Cd1 O4 81.10(6) . . ? O3 Cd1 O4 98.20(5) . . ? O2 Cd1 O4 136.58(5) . . ? O5 Cd1 N2 177.16(6) . . ? O3 Cd1 N2 87.13(6) . . ? O2 Cd1 N2 91.05(6) . . ? O4 Cd1 N2 101.73(5) . . ? O5 Cd1 O1 86.17(6) . . ? O3 Cd1 O1 176.39(5) . . ? O2 Cd1 O1 52.73(5) . . ? O4 Cd1 O1 84.75(5) . . ? N2 Cd1 O1 94.33(5) . . ? C23 O3 Cd1 107.50(12) . . ? C13 N2 C22 117.25(17) . . ? C13 N2 Cd1 112.88(13) . . ? C22 N2 Cd1 129.46(13) . . ? O4 C23 O3 122.82(17) 4_566 . ? O4 C23 C24 121.07(17) 4_566 . ? O3 C23 C24 116.04(16) . . ? C1 O1 Cd1 84.67(12) . . ? C14 C15 C17 116.91(18) . . ? C14 C15 C16 121.26(18) . . ? C17 C15 C16 121.62(17) . . ? C1 O2 Cd1 100.04(12) . . ? C23 O4 Cd1 144.82(13) 4_565 . ? C18 C17 C22 118.16(18) . . ? C18 C17 C15 123.49(18) . . ? C22 C17 C15 118.34(18) . . ? N2 C22 C21 118.55(19) . . ? N2 C22 C17 122.14(17) . . ? C21 C22 C17 119.30(19) . . ? C5 C4 C12 118.21(18) . . ? C5 C4 C3 120.5(2) . . ? C12 C4 C3 121.27(19) . . ? O1 C1 O2 122.52(18) . . ? O1 C1 C2 119.39(19) . . ? O2 C1 C2 118.08(18) . . ? C16 C24 C23 125.58(18) 2_656 . ? C24 C16 C15 125.11(18) 2_646 . ? C20 C21 C22 120.4(2) . . ? C21 C20 C19 120.8(2) . . ? C6 N1 C7 118.06(18) . . ? C2 C3 C4 125.7(2) . . ? C4 C5 C6 120.2(2) . . ? C15 C14 C13 121.14(19) . . ? N1 C7 C12 122.4(2) . . ? N1 C7 C8 118.5(2) . . ? C12 C7 C8 119.2(2) . . ? C11 C12 C7 118.4(2) . . ? C11 C12 C4 123.97(19) . . ? C7 C12 C4 117.7(2) . . ? C19 C18 C17 120.9(2) . . ? N2 C13 C14 123.97(19) . . ? C9 C8 C7 120.7(3) . . ? N1 C6 C5 123.5(2) . . ? C18 C19 C20 120.3(2) . . ? C3 C2 C1 122.9(2) . . ? C10 C11 C12 120.6(2) . . ? C11 C10 C9 120.5(3) . . ? C8 C9 C10 120.7(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 O5 Cd1 O3 C23 105.00(14) . . . . ? O2 Cd1 O3 C23 17.09(16) . . . . ? O4 Cd1 O3 C23 -173.68(13) . . . . ? N2 Cd1 O3 C23 -72.24(14) . . . . ? O1 Cd1 O3 C23 41.8(9) . . . . ? O5 Cd1 N2 C13 48.4(13) . . . . ? O3 Cd1 N2 C13 124.98(14) . . . . ? O2 Cd1 N2 C13 0.98(14) . . . . ? O4 Cd1 N2 C13 -137.24(14) . . . . ? O1 Cd1 N2 C13 -51.72(14) . . . . ? O5 Cd1 N2 C22 -139.2(12) . . . . ? O3 Cd1 N2 C22 -62.64(16) . . . . ? O2 Cd1 N2 C22 173.36(16) . . . . ? O4 Cd1 N2 C22 35.14(17) . . . . ? O1 Cd1 N2 C22 120.67(16) . . . . ? Cd1 O3 C23 O4 -11.4(2) . . . 4_566 ? Cd1 O3 C23 C24 165.41(15) . . . . ? O5 Cd1 O1 C1 -88.03(13) . . . . ? O3 Cd1 O1 C1 -24.6(9) . . . . ? O2 Cd1 O1 C1 1.15(12) . . . . ? O4 Cd1 O1 C1 -169.43(12) . . . . ? N2 Cd1 O1 C1 89.16(12) . . . . ? O5 Cd1 O2 C1 86.31(13) . . . . ? O3 Cd1 O2 C1 176.97(12) . . . . ? O4 Cd1 O2 C1 12.59(16) . . . . ? N2 Cd1 O2 C1 -95.78(13) . . . . ? O1 Cd1 O2 C1 -1.14(12) . . . . ? O5 Cd1 O4 C23 -156.9(2) . . . 4_565 ? O3 Cd1 O4 C23 112.1(2) . . . 4_565 ? O2 Cd1 O4 C23 -80.9(3) . . . 4_565 ? N2 Cd1 O4 C23 23.4(2) . . . 4_565 ? O1 Cd1 O4 C23 -70.0(2) . . . 4_565 ? C14 C15 C17 C18 177.7(2) . . . . ? C16 C15 C17 C18 -7.5(3) . . . . ? C14 C15 C17 C22 -3.7(3) . . . . ? C16 C15 C17 C22 171.04(17) . . . . ? C13 N2 C22 C21 -177.2(2) . . . . ? Cd1 N2 C22 C21 10.7(3) . . . . ? C13 N2 C22 C17 4.2(3) . . . . ? Cd1 N2 C22 C17 -167.92(14) . . . . ? C18 C17 C22 N2 178.35(18) . . . . ? C15 C17 C22 N2 -0.3(3) . . . . ? C18 C17 C22 C21 -0.2(3) . . . . ? C15 C17 C22 C21 -178.91(19) . . . . ? Cd1 O1 C1 O2 -1.9(2) . . . . ? Cd1 O1 C1 C2 179.65(18) . . . . ? Cd1 O2 C1 O1 2.3(2) . . . . ? Cd1 O2 C1 C2 -179.31(16) . . . . ? O4 C23 C24 C16 -30.3(3) 4_566 . . 2_656 ? O3 C23 C24 C16 152.8(2) . . . 2_656 ? C14 C15 C16 C24 -9.0(3) . . . 2_646 ? C17 C15 C16 C24 176.4(2) . . . 2_646 ? N2 C22 C21 C20 -178.1(2) . . . . ? C17 C22 C21 C20 0.6(4) . . . . ? C22 C21 C20 C19 -0.3(4) . . . . ? C5 C4 C3 C2 -47.0(3) . . . . ? C12 C4 C3 C2 135.6(2) . . . . ? C12 C4 C5 C6 0.7(3) . . . . ? C3 C4 C5 C6 -176.9(2) . . . . ? C17 C15 C14 C13 4.1(3) . . . . ? C16 C15 C14 C13 -170.75(19) . . . . ? C6 N1 C7 C12 0.3(3) . . . . ? C6 N1 C7 C8 179.5(2) . . . . ? N1 C7 C12 C11 179.9(2) . . . . ? C8 C7 C12 C11 0.7(3) . . . . ? N1 C7 C12 C4 0.3(3) . . . . ? C8 C7 C12 C4 -178.8(2) . . . . ? C5 C4 C12 C11 179.7(2) . . . . ? C3 C4 C12 C11 -2.8(3) . . . . ? C5 C4 C12 C7 -0.8(3) . . . . ? C3 C4 C12 C7 176.7(2) . . . . ? C22 C17 C18 C19 -0.4(3) . . . . ? C15 C17 C18 C19 178.2(2) . . . . ? C22 N2 C13 C14 -4.1(3) . . . . ? Cd1 N2 C13 C14 169.33(17) . . . . ? C15 C14 C13 N2 -0.1(3) . . . . ? N1 C7 C8 C9 -179.2(3) . . . . ? C12 C7 C8 C9 0.0(4) . . . . ? C7 N1 C6 C5 -0.5(3) . . . . ? C4 C5 C6 N1 0.0(4) . . . . ? C17 C18 C19 C20 0.7(4) . . . . ? C21 C20 C19 C18 -0.4(5) . . . . ? C4 C3 C2 C1 179.2(2) . . . . ? O1 C1 C2 C3 155.6(2) . . . . ? O2 C1 C2 C3 -22.9(3) . . . . ? C7 C12 C11 C10 -0.6(4) . . . . ? C4 C12 C11 C10 178.9(3) . . . . ? C12 C11 C10 C9 -0.3(5) . . . . ? C7 C8 C9 C10 -0.9(5) . . . . ? C11 C10 C9 C8 1.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.466 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 867076' ####################################################################### # # 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_lgl22 #TrackingRef 'lgl22.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H24 Cd N4 O4' _chemical_formula_weight 664.97 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' Cd Cd -0.8075 1.2024 '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 24.217(13) _cell_length_b 11.868(7) _cell_length_c 10.137(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.156(8) _cell_angle_gamma 90.00 _cell_volume 2848(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3262 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.26 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.814 _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 6542 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2462 _reflns_number_gt 2182 _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^)+(0.0795P)^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 2462 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Cd1 Cd 0.0000 0.03011(3) 0.7500 0.02589(18) Uani 1 2 d S . . O1 O 0.07910(12) 0.0460(3) 0.6668(3) 0.0428(8) Uani 1 1 d . . . O2 O 0.05890(12) -0.0449(2) 0.4674(3) 0.0377(7) Uani 1 1 d . . . C1 C 0.09137(16) 0.0083(3) 0.5592(4) 0.0286(8) Uani 1 1 d . . . C3 C 0.17552(17) -0.0158(3) 0.4550(4) 0.0320(9) Uani 1 1 d . . . H3 H 0.1527 -0.0580 0.3875 0.038 Uiso 1 1 calc R . . C15 C 0.0000 0.4670(4) 0.7500 0.0329(13) Uani 1 2 d S . . N2 N 0.0000 0.2305(4) 0.7500 0.0309(10) Uani 1 2 d S . . N3 N 0.0000 -0.1694(4) 0.7500 0.0335(10) Uani 1 2 d S . . C2 C 0.15172(18) 0.0290(3) 0.5493(4) 0.0371(10) Uani 1 1 d . . . H2 H 0.1736 0.0760 0.6130 0.045 Uiso 1 1 calc R . . N1 N 0.35111(16) 0.0268(3) 0.4328(5) 0.0504(11) Uani 1 1 d . . . C16 C 0.0000 0.5932(4) 0.7500 0.0305(12) Uani 1 2 d S . . C4 C 0.23563(17) -0.0032(4) 0.4499(4) 0.0319(8) Uani 1 1 d . . . C12 C 0.26472(16) -0.0900(4) 0.3926(4) 0.0341(9) Uani 1 1 d . . . C5 C 0.26612(17) 0.0915(4) 0.4991(4) 0.0402(9) Uani 1 1 d . . . H5 H 0.2492 0.1481 0.5402 0.048 Uiso 1 1 calc R . . C11 C 0.24001(18) -0.1962(3) 0.3475(4) 0.0399(10) Uani 1 1 d . . . H11 H 0.2022 -0.2094 0.3480 0.048 Uiso 1 1 calc R . . C17 C 0.02007(18) 0.6548(4) 0.8682(4) 0.0388(10) Uani 1 1 d . . . H17 H 0.0347 0.6177 0.9488 0.047 Uiso 1 1 calc R . . C18 C 0.01796(19) 0.7710(3) 0.8643(4) 0.0422(10) Uani 1 1 d . . . H18 H 0.0295 0.8102 0.9448 0.051 Uiso 1 1 calc R . . C7 C 0.32229(17) -0.0713(4) 0.3880(4) 0.0416(10) Uani 1 1 d . . . C6 C 0.32314(18) 0.1029(4) 0.4872(5) 0.0464(11) Uani 1 1 d . . . H6 H 0.3421 0.1686 0.5200 0.056 Uiso 1 1 calc R . . C9 C 0.3285(2) -0.2598(5) 0.2998(5) 0.0582(14) Uani 1 1 d . . . H9 H 0.3493 -0.3169 0.2707 0.070 Uiso 1 1 calc R . . C10 C 0.2713(2) -0.2788(4) 0.3037(5) 0.0497(12) Uani 1 1 d . . . H10 H 0.2548 -0.3480 0.2763 0.060 Uiso 1 1 calc R . . C8 C 0.35339(19) -0.1591(5) 0.3379(5) 0.0552(13) Uani 1 1 d . . . H8 H 0.3907 -0.1468 0.3317 0.066 Uiso 1 1 calc R . . C14 C 0.04499(19) 0.4061(3) 0.8227(5) 0.0509(12) Uani 1 1 d . . . H14 H 0.0764 0.4431 0.8725 0.061 Uiso 1 1 calc R . . C13 C 0.04288(19) 0.2886(3) 0.8208(5) 0.0500(12) Uani 1 1 d . . . H13 H 0.0731 0.2490 0.8718 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0305(3) 0.0116(2) 0.0365(3) 0.000 0.00916(17) 0.000 O1 0.0348(16) 0.0504(18) 0.0455(18) -0.0107(13) 0.0140(13) -0.0023(13) O2 0.0337(15) 0.0347(15) 0.0433(17) -0.0036(12) 0.0048(13) -0.0008(12) C1 0.031(2) 0.0238(17) 0.033(2) -0.0005(16) 0.0109(16) 0.0032(16) C3 0.033(2) 0.025(2) 0.039(2) -0.0011(16) 0.0091(17) -0.0001(16) C15 0.035(3) 0.015(3) 0.048(4) 0.000 0.008(3) 0.000 N2 0.039(2) 0.012(2) 0.042(3) 0.000 0.009(2) 0.000 N3 0.040(3) 0.013(2) 0.048(3) 0.000 0.010(2) 0.000 C2 0.035(2) 0.037(3) 0.039(2) -0.0096(17) 0.0086(18) -0.0073(17) N1 0.0309(19) 0.063(3) 0.057(3) 0.007(2) 0.0090(18) -0.0011(18) C16 0.029(3) 0.015(3) 0.049(3) 0.000 0.010(2) 0.000 C4 0.033(2) 0.0283(18) 0.036(2) 0.0019(18) 0.0097(16) 0.0020(17) C12 0.035(2) 0.036(2) 0.032(2) 0.0050(17) 0.0085(16) 0.0080(18) C5 0.043(2) 0.038(2) 0.042(2) 0.0002(19) 0.0127(18) -0.001(2) C11 0.048(2) 0.037(2) 0.035(2) 0.0006(18) 0.0095(18) 0.0053(19) C17 0.053(2) 0.0190(19) 0.042(2) 0.0037(17) 0.0042(19) -0.0010(18) C18 0.059(3) 0.0172(19) 0.046(3) -0.0006(17) 0.001(2) -0.0044(19) C7 0.037(2) 0.048(3) 0.040(2) 0.007(2) 0.0087(18) 0.009(2) C6 0.038(2) 0.049(3) 0.051(3) 0.001(2) 0.0090(19) -0.008(2) C9 0.072(3) 0.055(3) 0.053(3) 0.009(2) 0.027(3) 0.034(3) C10 0.078(3) 0.034(2) 0.038(2) -0.0014(18) 0.015(2) 0.011(2) C8 0.042(2) 0.071(4) 0.055(3) 0.009(3) 0.016(2) 0.022(3) C14 0.045(2) 0.0172(19) 0.079(3) -0.001(2) -0.012(2) -0.0020(19) C13 0.045(2) 0.017(2) 0.077(3) 0.003(2) -0.013(2) 0.0031(19) _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 Cd1 O1 2.258(3) . ? Cd1 O1 2.258(3) 2_556 ? Cd1 O2 2.366(3) 6_556 ? Cd1 O2 2.366(3) 5_556 ? Cd1 N3 2.367(5) . ? Cd1 N2 2.379(4) . ? O1 C1 1.270(5) . ? O2 C1 1.255(5) . ? O2 Cd1 2.366(3) 5_556 ? C1 C2 1.506(6) . ? C3 C2 1.327(6) . ? C3 C4 1.475(5) . ? C15 C14 1.384(5) 2_556 ? C15 C14 1.384(5) . ? C15 C16 1.497(8) . ? N2 C13 1.324(5) . ? N2 C13 1.324(5) 2_556 ? N3 C18 1.350(5) 1_545 ? N3 C18 1.350(5) 2_546 ? N1 C6 1.317(6) . ? N1 C7 1.384(6) . ? C16 C17 1.401(5) . ? C16 C17 1.401(5) 2_556 ? C4 C5 1.379(6) . ? C4 C12 1.438(6) . ? C12 C7 1.422(5) . ? C12 C11 1.429(6) . ? C5 C6 1.418(6) . ? C11 C10 1.369(6) . ? C17 C18 1.380(6) . ? C18 N3 1.350(5) 1_565 ? C7 C8 1.439(7) . ? C9 C8 1.358(8) . ? C9 C10 1.411(7) . ? C14 C13 1.395(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 O1 170.42(16) . 2_556 ? O1 Cd1 O2 87.09(11) . 6_556 ? O1 Cd1 O2 92.20(12) 2_556 6_556 ? O1 Cd1 O2 92.20(12) . 5_556 ? O1 Cd1 O2 87.09(11) 2_556 5_556 ? O2 Cd1 O2 171.49(13) 6_556 5_556 ? O1 Cd1 N3 94.79(8) . . ? O1 Cd1 N3 94.79(8) 2_556 . ? O2 Cd1 N3 94.26(7) 6_556 . ? O2 Cd1 N3 94.26(7) 5_556 . ? O1 Cd1 N2 85.21(8) . . ? O1 Cd1 N2 85.21(8) 2_556 . ? O2 Cd1 N2 85.74(7) 6_556 . ? O2 Cd1 N2 85.74(7) 5_556 . ? N3 Cd1 N2 180.000(1) . . ? C1 O1 Cd1 131.4(3) . . ? C1 O2 Cd1 144.5(3) . 5_556 ? O2 C1 O1 126.2(4) . . ? O2 C1 C2 119.8(3) . . ? O1 C1 C2 113.9(3) . . ? C2 C3 C4 124.5(4) . . ? C14 C15 C14 117.0(5) 2_556 . ? C14 C15 C16 121.5(2) 2_556 . ? C14 C15 C16 121.5(2) . . ? C13 N2 C13 117.3(5) . 2_556 ? C13 N2 Cd1 121.3(2) . . ? C13 N2 Cd1 121.3(2) 2_556 . ? C18 N3 C18 116.7(5) 1_545 2_546 ? C18 N3 Cd1 121.7(2) 1_545 . ? C18 N3 Cd1 121.7(2) 2_546 . ? C3 C2 C1 123.9(4) . . ? C6 N1 C7 116.5(4) . . ? C17 C16 C17 117.0(5) . 2_556 ? C17 C16 C15 121.5(2) . . ? C17 C16 C15 121.5(2) 2_556 . ? C5 C4 C12 117.4(4) . . ? C5 C4 C3 121.8(4) . . ? C12 C4 C3 120.8(4) . . ? C7 C12 C11 118.3(4) . . ? C7 C12 C4 118.0(4) . . ? C11 C12 C4 123.6(4) . . ? C4 C5 C6 120.3(4) . . ? C10 C11 C12 120.8(4) . . ? C18 C17 C16 119.5(4) . . ? N3 C18 C17 123.5(4) 1_565 . ? N1 C7 C12 123.4(4) . . ? N1 C7 C8 117.4(4) . . ? C12 C7 C8 119.2(4) . . ? N1 C6 C5 124.5(4) . . ? C8 C9 C10 120.9(4) . . ? C11 C10 C9 120.5(5) . . ? C9 C8 C7 120.2(4) . . ? C15 C14 C13 119.5(4) . . ? N2 C13 C14 123.3(4) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.415 _refine_diff_density_min -1.657 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 867077'