# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_ba9 #TrackingRef '- DDC13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 N O3' _chemical_formula_sum 'C16 H11 N O3' _chemical_formula_weight 265.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7162(10) _cell_length_b 15.008(3) _cell_length_c 15.078(2) _cell_angle_alpha 74.238(12) _cell_angle_beta 83.545(13) _cell_angle_gamma 80.741(14) _cell_volume 1225.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5167 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.0 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.101 _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 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16166 _diffrn_reflns_av_R_equivalents 0.1110 _diffrn_reflns_av_sigmaI/netI 0.1245 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.96 _reflns_number_total 4563 _reflns_number_gt 2728 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0816P)^2^] 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 4563 _refine_ls_number_parameters 368 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1470 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.2091 _refine_ls_wR_factor_gt 0.1841 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 N1 N 0.5339(5) 0.6019(2) 0.1111(2) 0.0282(7) Uani 1 1 d . . . O1 O 0.8825(4) 0.69403(17) 0.03509(18) 0.0358(6) Uani 1 1 d D . . H1 H 0.820(6) 0.6469(17) 0.062(2) 0.054 Uiso 1 1 d D . . O2 O 0.1536(4) 0.26659(17) 0.19304(16) 0.0324(6) Uani 1 1 d . . . O3 O 0.1741(4) 0.11986(18) 0.18836(18) 0.0433(7) Uani 1 1 d . . . C1 C 0.4302(6) 0.6732(3) 0.1358(3) 0.0346(9) Uani 1 1 d . . . H1B H 0.2791 0.6707 0.1691 0.042 Uiso 1 1 calc R . . C2 C 0.4262(6) 0.5175(2) 0.1324(2) 0.0258(8) Uani 1 1 d . . . C3 C 0.5619(6) 0.4417(3) 0.1073(2) 0.0302(8) Uani 1 1 d . . . H3 H 0.7139 0.4485 0.0756 0.036 Uiso 1 1 calc R . . C4 C 0.4772(5) 0.3554(3) 0.1281(2) 0.0280(8) Uani 1 1 d . . . C5 C 0.2484(5) 0.3494(2) 0.1701(2) 0.0257(7) Uani 1 1 d . . . C6 C 0.1101(5) 0.4247(2) 0.1940(2) 0.0314(8) Uani 1 1 d . . . H6 H -0.0454 0.4187 0.2226 0.038 Uiso 1 1 calc R . . C7 C 0.1975(5) 0.5088(3) 0.1763(2) 0.0318(8) Uani 1 1 d . . . H7 H 0.1038 0.5606 0.1936 0.038 Uiso 1 1 calc R . . C8 C 0.2759(6) 0.1874(3) 0.1699(3) 0.0372(9) Uani 1 1 d . . . C9 C 0.5174(6) 0.1921(2) 0.1285(2) 0.0346(9) Uani 1 1 d . . . H9 H 0.6097 0.1383 0.1148 0.041 Uiso 1 1 calc R . . C10 C 0.6108(6) 0.2734(2) 0.1093(2) 0.0302(8) Uani 1 1 d . . . H10 H 0.7692 0.2755 0.0827 0.036 Uiso 1 1 calc R . . C11 C 0.5356(6) 0.7580(3) 0.1148(2) 0.0312(8) Uani 1 1 d . . . C12 C 0.7582(6) 0.7661(2) 0.0655(2) 0.0315(8) Uani 1 1 d . . . C13 C 0.8563(6) 0.8491(3) 0.0482(3) 0.0402(9) Uani 1 1 d . . . H13 H 1.0097 0.8536 0.0171 0.048 Uiso 1 1 calc R . . C14 C 0.7326(7) 0.9241(2) 0.0760(3) 0.0408(9) Uani 1 1 d . . . H14 H 0.8006 0.9805 0.0622 0.049 Uiso 1 1 calc R . . C15 C 0.5080(7) 0.9200(3) 0.1241(3) 0.0404(9) Uani 1 1 d . . . H15 H 0.4230 0.9723 0.1431 0.048 Uiso 1 1 calc R . . C16 C 0.4154(6) 0.8366(2) 0.1428(2) 0.0320(8) Uani 1 1 d . . . H16 H 0.2644 0.8322 0.1760 0.038 Uiso 1 1 calc R . . N1A N 0.4434(4) 0.10622(19) 0.38579(19) 0.0255(7) Uani 1 1 d . . . O1A O 0.0750(4) 0.20369(16) 0.45031(18) 0.0336(6) Uani 1 1 d D . . H1A H 0.156(6) 0.165(2) 0.426(2) 0.050 Uiso 1 1 d D . . O2A O 0.8534(4) -0.22999(17) 0.30835(17) 0.0342(6) Uani 1 1 d . . . O3A O 0.8421(4) -0.37546(17) 0.30877(18) 0.0426(7) Uani 1 1 d . . . C1A C 0.5512(5) 0.1789(2) 0.3675(2) 0.0247(8) Uani 1 1 d . . . H1A1 H 0.7090 0.1755 0.3399 0.030 Uiso 1 1 calc R . . C2A C 0.5577(5) 0.0218(2) 0.3651(2) 0.0258(8) Uani 1 1 d . . . C3A C 0.4281(5) -0.0528(2) 0.3916(2) 0.0287(8) Uani 1 1 d . . . H3A H 0.2747 -0.0456 0.4224 0.034 Uiso 1 1 calc R . . C4A C 0.5219(6) -0.1390(2) 0.3730(2) 0.0245(7) Uani 1 1 d . . . C5A C 0.7491(5) -0.1473(2) 0.3291(2) 0.0274(8) Uani 1 1 d . . . C6A C 0.8782(6) -0.0732(2) 0.3015(2) 0.0317(8) Uani 1 1 d . . . H6A H 1.0313 -0.0803 0.2703 0.038 Uiso 1 1 calc R . . C7A C 0.7839(5) 0.0115(2) 0.3194(2) 0.0318(8) Uani 1 1 d . . . H7A H 0.8725 0.0628 0.3007 0.038 Uiso 1 1 calc R . . C8A C 0.7337(6) -0.3067(2) 0.3277(2) 0.0314(8) Uani 1 1 d . . . C9A C 0.4972(6) -0.2984(2) 0.3723(2) 0.0344(9) Uani 1 1 d . . . H9A H 0.4089 -0.3496 0.3857 0.041 Uiso 1 1 calc R . . C10A C 0.3994(6) -0.2187(2) 0.3954(2) 0.0290(8) Uani 1 1 d . . . H10A H 0.2461 -0.2158 0.4270 0.035 Uiso 1 1 calc R . . C11A C 0.4395(6) 0.2657(2) 0.3878(2) 0.0288(8) Uani 1 1 d . . . C12A C 0.2073(5) 0.2758(2) 0.4290(2) 0.0263(7) Uani 1 1 d . . . C13A C 0.1079(6) 0.3602(2) 0.4462(2) 0.0324(8) Uani 1 1 d . . . H13A H -0.0499 0.3670 0.4734 0.039 Uiso 1 1 calc R . . C14A C 0.2364(6) 0.4351(3) 0.4239(3) 0.0383(9) Uani 1 1 d . . . H14A H 0.1663 0.4927 0.4364 0.046 Uiso 1 1 calc R . . C15A C 0.4685(6) 0.4267(2) 0.3833(3) 0.0350(8) Uani 1 1 d . . . H15A H 0.5564 0.4781 0.3672 0.042 Uiso 1 1 calc R . . C16A C 0.5670(6) 0.3411(2) 0.3671(2) 0.0300(8) Uani 1 1 d . . . H16A H 0.7261 0.3339 0.3412 0.036 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 N1 0.0238(14) 0.0313(17) 0.0280(17) -0.0072(14) 0.0043(12) -0.0048(12) O1 0.0342(13) 0.0291(14) 0.0431(16) -0.0102(12) 0.0087(11) -0.0079(11) O2 0.0257(12) 0.0386(15) 0.0317(15) -0.0023(12) 0.0018(10) -0.0149(11) O3 0.0412(14) 0.0377(15) 0.0514(18) -0.0082(13) 0.0046(12) -0.0180(12) C1 0.0245(17) 0.048(2) 0.033(2) -0.014(2) 0.0012(15) -0.0075(17) C2 0.0292(17) 0.0224(19) 0.027(2) -0.0060(15) -0.0001(14) -0.0080(14) C3 0.0252(17) 0.039(2) 0.024(2) -0.0038(16) 0.0002(14) -0.0070(15) C4 0.0205(16) 0.038(2) 0.0245(19) -0.0051(16) 0.0005(13) -0.0065(14) C5 0.0272(16) 0.0306(19) 0.0204(18) -0.0054(15) -0.0001(13) -0.0103(14) C6 0.0232(16) 0.037(2) 0.030(2) -0.0045(16) 0.0037(14) -0.0049(14) C7 0.0250(16) 0.039(2) 0.0282(19) -0.0073(17) 0.0053(13) -0.0031(15) C8 0.0362(19) 0.037(2) 0.032(2) 0.0027(16) 0.0018(15) -0.0109(17) C9 0.0304(18) 0.036(2) 0.035(2) -0.0097(18) 0.0091(15) -0.0074(16) C10 0.0246(16) 0.035(2) 0.030(2) -0.0074(16) -0.0030(14) -0.0030(14) C11 0.0333(18) 0.038(2) 0.023(2) -0.0090(17) -0.0012(15) -0.0062(16) C12 0.0297(18) 0.032(2) 0.029(2) -0.0016(16) -0.0015(15) -0.0029(15) C13 0.039(2) 0.044(2) 0.038(2) -0.0082(19) 0.0007(17) -0.0139(18) C14 0.051(2) 0.030(2) 0.044(2) -0.0111(18) -0.0032(18) -0.0112(17) C15 0.042(2) 0.035(2) 0.040(2) -0.0055(18) -0.0021(17) -0.0016(17) C16 0.0341(19) 0.034(2) 0.030(2) -0.0126(17) -0.0034(15) -0.0021(15) N1A 0.0232(14) 0.0288(17) 0.0249(16) -0.0065(13) 0.0010(11) -0.0073(12) O1A 0.0231(11) 0.0286(13) 0.0478(16) -0.0104(12) 0.0069(10) -0.0051(9) O2A 0.0261(12) 0.0349(14) 0.0394(16) -0.0135(12) 0.0056(10) 0.0038(10) O3A 0.0479(15) 0.0318(15) 0.0488(17) -0.0190(13) 0.0038(12) 0.0021(12) C1A 0.0198(15) 0.0303(19) 0.0220(19) -0.0056(15) 0.0001(13) -0.0006(13) C2A 0.0236(16) 0.0278(19) 0.027(2) -0.0104(16) 0.0004(14) -0.0029(14) C3A 0.0199(15) 0.036(2) 0.0258(19) -0.0046(16) 0.0027(13) -0.0003(14) C4A 0.0219(15) 0.0253(17) 0.0252(19) -0.0057(15) -0.0009(13) -0.0020(13) C5A 0.0233(16) 0.035(2) 0.0236(19) -0.0099(16) 0.0006(13) -0.0010(14) C6A 0.0238(16) 0.036(2) 0.036(2) -0.0138(17) 0.0065(14) -0.0045(14) C7A 0.0248(16) 0.036(2) 0.034(2) -0.0064(16) 0.0043(14) -0.0096(14) C8A 0.0387(19) 0.0275(19) 0.029(2) -0.0091(16) -0.0038(15) -0.0026(15) C9A 0.0366(19) 0.035(2) 0.033(2) -0.0102(17) 0.0025(16) -0.0086(16) C10A 0.0253(16) 0.0265(18) 0.033(2) -0.0053(16) 0.0006(14) -0.0032(14) C11A 0.0257(17) 0.035(2) 0.026(2) -0.0072(17) -0.0022(14) -0.0053(15) C12A 0.0280(16) 0.0281(18) 0.0243(19) -0.0074(15) 0.0032(14) -0.0112(14) C13A 0.0234(16) 0.040(2) 0.038(2) -0.0162(18) -0.0025(14) -0.0046(15) C14A 0.039(2) 0.032(2) 0.038(2) -0.0024(17) -0.0003(16) 0.0011(16) C15A 0.0369(19) 0.0255(19) 0.042(2) -0.0048(16) -0.0037(16) -0.0094(15) C16A 0.0266(16) 0.037(2) 0.029(2) -0.0099(16) -0.0010(14) -0.0101(15) _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 N1 C1 1.264(4) . ? N1 C2 1.439(4) . ? O1 C12 1.354(4) . ? O1 H1 0.825(10) . ? O2 C5 1.378(4) . ? O2 C8 1.388(4) . ? O3 C8 1.202(4) . ? C1 C11 1.438(5) . ? C1 H1B 0.9500 . ? C2 C3 1.387(5) . ? C2 C7 1.406(4) . ? C3 C4 1.399(5) . ? C3 H3 0.9500 . ? C4 C5 1.393(4) . ? C4 C10 1.421(5) . ? C5 C6 1.379(5) . ? C6 C7 1.381(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.454(4) . ? C9 C10 1.356(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.406(4) . ? C11 C16 1.410(5) . ? C12 C13 1.397(5) . ? C13 C14 1.369(5) . ? C13 H13 0.9500 . ? C14 C15 1.404(5) . ? C14 H14 0.9500 . ? C15 C16 1.382(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N1A C1A 1.289(4) . ? N1A C2A 1.426(4) . ? O1A C12A 1.366(4) . ? O1A H1A 0.831(10) . ? O2A C8A 1.381(4) . ? O2A C5A 1.387(4) . ? O3A C8A 1.201(4) . ? C1A C11A 1.450(5) . ? C1A H1A1 0.9500 . ? C2A C3A 1.384(5) . ? C2A C7A 1.402(4) . ? C3A C4A 1.408(5) . ? C3A H3A 0.9500 . ? C4A C5A 1.393(4) . ? C4A C10A 1.425(4) . ? C5A C6A 1.378(5) . ? C6A C7A 1.383(5) . ? C6A H6A 0.9500 . ? C7A H7A 0.9500 . ? C8A C9A 1.443(5) . ? C9A C10A 1.354(5) . ? C9A H9A 0.9500 . ? C10A H10A 0.9500 . ? C11A C16A 1.390(5) . ? C11A C12A 1.404(4) . ? C12A C13A 1.381(5) . ? C13A C14A 1.386(5) . ? C13A H13A 0.9500 . ? C14A C15A 1.399(5) . ? C14A H14A 0.9500 . ? C15A C16A 1.390(5) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? 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 C1 N1 C2 121.0(3) . . ? C12 O1 H1 107(3) . . ? C5 O2 C8 121.4(3) . . ? N1 C1 C11 121.6(3) . . ? N1 C1 H1B 119.2 . . ? C11 C1 H1B 119.2 . . ? C3 C2 C7 119.9(3) . . ? C3 C2 N1 116.2(3) . . ? C7 C2 N1 123.9(3) . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.1(3) . . ? C5 C4 C10 118.0(3) . . ? C3 C4 C10 123.9(3) . . ? O2 C5 C6 116.9(3) . . ? O2 C5 C4 121.3(3) . . ? C6 C5 C4 121.7(3) . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C2 119.6(3) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O3 C8 O2 116.7(3) . . ? O3 C8 C9 125.7(4) . . ? O2 C8 C9 117.6(3) . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C4 121.5(3) . . ? C9 C10 H10 119.2 . . ? C4 C10 H10 119.2 . . ? C12 C11 C16 117.7(3) . . ? C12 C11 C1 121.9(3) . . ? C16 C11 C1 120.4(3) . . ? O1 C12 C13 118.9(3) . . ? O1 C12 C11 121.1(3) . . ? C13 C12 C11 120.0(3) . . ? C14 C13 C12 120.3(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.8(3) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 117.3(4) . . ? C16 C15 H15 121.4 . . ? C14 C15 H15 121.4 . . ? C15 C16 C11 122.8(4) . . ? C15 C16 H16 118.6 . . ? C11 C16 H16 118.6 . . ? C1A N1A C2A 120.9(3) . . ? C12A O1A H1A 103(3) . . ? C8A O2A C5A 121.5(3) . . ? N1A C1A C11A 122.2(3) . . ? N1A C1A H1A1 118.9 . . ? C11A C1A H1A1 118.9 . . ? C3A C2A C7A 119.9(3) . . ? C3A C2A N1A 115.7(3) . . ? C7A C2A N1A 124.4(3) . . ? C2A C3A C4A 120.5(3) . . ? C2A C3A H3A 119.7 . . ? C4A C3A H3A 119.7 . . ? C5A C4A C3A 118.1(3) . . ? C5A C4A C10A 117.4(3) . . ? C3A C4A C10A 124.5(3) . . ? C6A C5A O2A 116.7(3) . . ? C6A C5A C4A 121.8(3) . . ? O2A C5A C4A 121.4(3) . . ? C5A C6A C7A 119.7(3) . . ? C5A C6A H6A 120.2 . . ? C7A C6A H6A 120.2 . . ? C6A C7A C2A 120.0(3) . . ? C6A C7A H7A 120.0 . . ? C2A C7A H7A 120.0 . . ? O3A C8A O2A 116.1(3) . . ? O3A C8A C9A 126.4(3) . . ? O2A C8A C9A 117.4(3) . . ? C10A C9A C8A 120.9(3) . . ? C10A C9A H9A 119.6 . . ? C8A C9A H9A 119.6 . . ? C9A C10A C4A 121.3(3) . . ? C9A C10A H10A 119.4 . . ? C4A C10A H10A 119.4 . . ? C16A C11A C12A 118.7(3) . . ? C16A C11A C1A 119.1(3) . . ? C12A C11A C1A 122.1(3) . . ? O1A C12A C13A 119.2(3) . . ? O1A C12A C11A 120.8(3) . . ? C13A C12A C11A 120.0(3) . . ? C12A C13A C14A 120.5(3) . . ? C12A C13A H13A 119.7 . . ? C14A C13A H13A 119.7 . . ? C13A C14A C15A 120.6(3) . . ? C13A C14A H14A 119.7 . . ? C15A C14A H14A 119.7 . . ? C16A C15A C14A 118.3(3) . . ? C16A C15A H15A 120.9 . . ? C14A C15A H15A 120.9 . . ? C11A C16A C15A 121.9(3) . . ? C11A C16A H16A 119.1 . . ? C15A C16A H16A 119.1 . . ? 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 C2 N1 C1 C11 -179.9(4) . . . . ? C1 N1 C2 C3 -176.0(4) . . . . ? C1 N1 C2 C7 3.9(5) . . . . ? C7 C2 C3 C4 -2.4(5) . . . . ? N1 C2 C3 C4 177.5(3) . . . . ? C2 C3 C4 C5 3.5(5) . . . . ? C2 C3 C4 C10 -176.3(4) . . . . ? C8 O2 C5 C6 178.3(3) . . . . ? C8 O2 C5 C4 -4.2(5) . . . . ? C3 C4 C5 O2 -179.7(3) . . . . ? C10 C4 C5 O2 0.1(5) . . . . ? C3 C4 C5 C6 -2.4(5) . . . . ? C10 C4 C5 C6 177.5(3) . . . . ? O2 C5 C6 C7 177.5(3) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C2 1.1(5) . . . . ? C3 C2 C7 C6 0.1(5) . . . . ? N1 C2 C7 C6 -179.8(3) . . . . ? C5 O2 C8 O3 -176.1(3) . . . . ? C5 O2 C8 C9 5.8(5) . . . . ? O3 C8 C9 C10 178.7(4) . . . . ? O2 C8 C9 C10 -3.4(5) . . . . ? C8 C9 C10 C4 -0.5(6) . . . . ? C5 C4 C10 C9 2.2(5) . . . . ? C3 C4 C10 C9 -178.0(4) . . . . ? N1 C1 C11 C12 0.3(6) . . . . ? N1 C1 C11 C16 179.7(4) . . . . ? C16 C11 C12 O1 -179.0(3) . . . . ? C1 C11 C12 O1 0.4(5) . . . . ? C16 C11 C12 C13 2.0(5) . . . . ? C1 C11 C12 C13 -178.6(4) . . . . ? O1 C12 C13 C14 178.3(4) . . . . ? C11 C12 C13 C14 -2.6(5) . . . . ? C12 C13 C14 C15 1.6(6) . . . . ? C13 C14 C15 C16 0.1(6) . . . . ? C14 C15 C16 C11 -0.7(6) . . . . ? C12 C11 C16 C15 -0.3(5) . . . . ? C1 C11 C16 C15 -179.7(4) . . . . ? C2A N1A C1A C11A -180.0(3) . . . . ? C1A N1A C2A C3A 177.3(4) . . . . ? C1A N1A C2A C7A -4.1(5) . . . . ? C7A C2A C3A C4A 0.1(5) . . . . ? N1A C2A C3A C4A 178.8(3) . . . . ? C2A C3A C4A C5A 1.1(5) . . . . ? C2A C3A C4A C10A -178.2(4) . . . . ? C8A O2A C5A C6A -175.9(4) . . . . ? C8A O2A C5A C4A 2.1(5) . . . . ? C3A C4A C5A C6A -1.9(5) . . . . ? C10A C4A C5A C6A 177.5(4) . . . . ? C3A C4A C5A O2A -179.9(3) . . . . ? C10A C4A C5A O2A -0.5(5) . . . . ? O2A C5A C6A C7A 179.5(3) . . . . ? C4A C5A C6A C7A 1.5(5) . . . . ? C5A C6A C7A C2A -0.2(5) . . . . ? C3A C2A C7A C6A -0.6(5) . . . . ? N1A C2A C7A C6A -179.2(3) . . . . ? C5A O2A C8A O3A -178.4(3) . . . . ? C5A O2A C8A C9A -1.4(5) . . . . ? O3A C8A C9A C10A 175.7(4) . . . . ? O2A C8A C9A C10A -1.0(5) . . . . ? C8A C9A C10A C4A 2.6(5) . . . . ? C5A C4A C10A C9A -1.9(5) . . . . ? C3A C4A C10A C9A 177.5(4) . . . . ? N1A C1A C11A C16A 179.4(4) . . . . ? N1A C1A C11A C12A 0.3(5) . . . . ? C16A C11A C12A O1A 179.8(3) . . . . ? C1A C11A C12A O1A -1.2(5) . . . . ? C16A C11A C12A C13A 1.6(5) . . . . ? C1A C11A C12A C13A -179.4(3) . . . . ? O1A C12A C13A C14A -178.9(4) . . . . ? C11A C12A C13A C14A -0.7(5) . . . . ? C12A C13A C14A C15A 0.3(5) . . . . ? C13A C14A C15A C16A -0.8(6) . . . . ? C12A C11A C16A C15A -2.1(5) . . . . ? C1A C11A C16A C15A 178.8(3) . . . . ? C14A C15A C16A C11A 1.8(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.825(10) 1.87(2) 2.590(4) 145(4) . O1A H1A N1A 0.831(10) 1.85(2) 2.616(4) 152(4) . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.211 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 857625'