# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O3' _chemical_formula_sum 'C18 H17 N O3' _chemical_formula_weight 295.33 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.3972(2) _cell_length_b 16.1308(3) _cell_length_c 19.6022(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2971.39(10) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6558 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 32.15 _exptl_crystal_description Block _exptl_crystal_colour white _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ' SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 APEXII 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 10291 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4477 _reflns_number_gt 4074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII, Bruker,2004' _computing_cell_refinement 'APEXII/SAINT, Bruker,2004' _computing_data_reduction 'SAINT PLUS/XPREP, Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0427P)^2^+0.6507P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(10) _refine_ls_number_reflns 4477 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0813 _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 C1A C 0.5849(3) 0.68906(12) 0.42261(10) 0.0413(5) Uani 1 1 d . . . H1A H 0.5815 0.6944 0.4698 0.050 Uiso 1 1 calc R . . C2A C 0.6182(3) 0.61418(13) 0.39344(12) 0.0508(6) Uani 1 1 d . . . H2A H 0.6378 0.5689 0.4213 0.061 Uiso 1 1 calc R . . C3A C 0.6232(3) 0.60480(14) 0.32240(12) 0.0548(6) Uani 1 1 d . . . H3A H 0.6467 0.5534 0.3040 0.066 Uiso 1 1 calc R . . C4A C 0.5945(3) 0.66915(14) 0.27964(10) 0.0486(6) Uani 1 1 d . . . H4A H 0.5963 0.6625 0.2325 0.058 Uiso 1 1 calc R . . C5A C 0.5623(2) 0.74547(12) 0.30922(9) 0.0383(5) Uani 1 1 d . . . C6A C 0.5152(3) 0.87897(13) 0.32813(9) 0.0448(6) Uani 1 1 d . . . C7A C 0.5049(4) 0.96847(16) 0.31184(14) 0.0836(11) Uani 1 1 d . . . H7A1 H 0.5930 0.9945 0.3262 0.100 Uiso 1 1 calc R . . H7A2 H 0.4997 0.9737 0.2626 0.100 Uiso 1 1 calc R . . C8A C 0.3187(3) 0.97705(16) 0.39427(10) 0.0531(6) Uani 1 1 d . . . H8A1 H 0.2738 0.9265 0.3783 0.064 Uiso 1 1 calc R . . H8A2 H 0.2437 1.0148 0.4080 0.064 Uiso 1 1 calc R . . C9A C 0.4075(3) 0.95686(11) 0.45569(9) 0.0376(5) Uani 1 1 d . . . C10A C 0.3889(3) 1.00222(12) 0.51568(9) 0.0396(5) Uani 1 1 d . . . H10A H 0.3303 1.0487 0.5153 0.048 Uiso 1 1 calc R . . C11A C 0.4556(3) 0.97947(12) 0.57544(9) 0.0374(5) Uani 1 1 d . . . C12A C 0.5466(2) 0.91109(11) 0.57543(8) 0.0325(5) Uani 1 1 d . . . C13A C 0.5701(2) 0.86757(11) 0.51581(8) 0.0337(5) Uani 1 1 d . . . H13A H 0.6329 0.8230 0.5160 0.040 Uiso 1 1 calc R . . C14A C 0.5010(2) 0.88940(11) 0.45512(9) 0.0344(5) Uani 1 1 d . . . C15A C 0.5240(2) 0.84310(12) 0.39147(9) 0.0353(5) Uani 1 1 d . . . C16A C 0.5562(2) 0.75727(11) 0.38063(8) 0.0332(4) Uani 1 1 d . . . C17A C 0.3491(3) 1.08925(14) 0.63950(13) 0.0604(7) Uani 1 1 d . . . H17A H 0.3864 1.1320 0.6105 0.091 Uiso 1 1 calc R . . H17B H 0.3434 1.1094 0.6855 0.091 Uiso 1 1 calc R . . H17C H 0.2558 1.0738 0.6240 0.091 Uiso 1 1 calc R . . C18A C 0.7139(3) 0.82955(13) 0.63784(11) 0.0486(6) Uani 1 1 d . . . H18A H 0.6710 0.7776 0.6256 0.073 Uiso 1 1 calc R . . H18B H 0.7540 0.8254 0.6828 0.073 Uiso 1 1 calc R . . H18C H 0.7876 0.8428 0.6058 0.073 Uiso 1 1 calc R . . C1B C 0.5789(3) 1.08408(11) 0.93565(9) 0.0356(5) Uani 1 1 d . . . H1B H 0.5754 1.0715 0.9819 0.043 Uiso 1 1 calc R . . C2B C 0.6024(3) 1.16422(12) 0.91446(10) 0.0405(5) Uani 1 1 d . . . H2B H 0.6150 1.2057 0.9469 0.049 Uiso 1 1 calc R . . C3B C 0.6077(3) 1.18458(12) 0.84557(11) 0.0454(5) Uani 1 1 d . . . H3B H 0.6247 1.2392 0.8328 0.055 Uiso 1 1 calc R . . C4B C 0.5884(3) 1.12566(12) 0.79628(9) 0.0439(5) Uani 1 1 d . . . H4B H 0.5913 1.1393 0.7502 0.053 Uiso 1 1 calc R . . C5B C 0.5642(2) 1.04442(12) 0.81754(9) 0.0360(5) Uani 1 1 d . . . C6B C 0.5102(2) 0.90903(12) 0.82249(8) 0.0351(5) Uani 1 1 d . . . C7B C 0.4704(3) 0.82806(12) 0.79064(9) 0.0476(6) Uani 1 1 d . . . H7B1 H 0.3903 0.8371 0.7603 0.057 Uiso 1 1 calc R . . H7B2 H 0.5496 0.8089 0.7631 0.057 Uiso 1 1 calc R . . C8B C 0.3322(3) 0.79192(14) 0.88703(10) 0.0466(6) Uani 1 1 d . . . H8B1 H 0.2669 0.7469 0.8967 0.056 Uiso 1 1 calc R . . H8B2 H 0.2775 0.8379 0.8689 0.056 Uiso 1 1 calc R . . C9B C 0.4047(3) 0.81819(11) 0.95154(9) 0.0345(5) Uani 1 1 d . . . C10B C 0.3789(3) 0.77472(11) 1.01206(9) 0.0385(5) Uani 1 1 d . . . H10B H 0.3163 0.7301 1.0116 0.046 Uiso 1 1 calc R . . C11B C 0.4443(3) 0.79670(11) 1.07242(9) 0.0354(5) Uani 1 1 d . . . C12B C 0.5390(2) 0.86335(10) 1.07253(8) 0.0307(4) Uani 1 1 d . . . C13B C 0.5683(2) 0.90482(10) 1.01256(8) 0.0309(4) Uani 1 1 d . . . H13B H 0.6352 0.9473 1.0128 0.037 Uiso 1 1 calc R . . C14B C 0.4994(2) 0.88436(10) 0.95125(8) 0.0295(4) Uani 1 1 d . . . C15B C 0.5257(2) 0.93392(10) 0.88937(8) 0.0295(4) Uani 1 1 d . . . C16B C 0.5602(2) 1.02146(11) 0.88687(8) 0.0303(4) Uani 1 1 d . . . C17B C 0.3313(4) 0.68943(16) 1.13555(12) 0.0678(8) Uani 1 1 d . . . H17D H 0.2398 0.7051 1.1179 0.102 Uiso 1 1 calc R . . H17E H 0.3210 0.6704 1.1817 0.102 Uiso 1 1 calc R . . H17F H 0.3704 0.6458 1.1081 0.102 Uiso 1 1 calc R . . C18B C 0.6985(3) 0.94723(14) 1.13685(11) 0.0526(6) Uani 1 1 d . . . H18D H 0.7792 0.9333 1.1091 0.079 Uiso 1 1 calc R . . H18E H 0.7289 0.9556 1.1831 0.079 Uiso 1 1 calc R . . H18F H 0.6555 0.9971 1.1199 0.079 Uiso 1 1 calc R . . N1A N 0.5357(2) 0.82016(11) 0.27889(8) 0.0485(5) Uani 1 1 d . . . H1A1 H 0.5324 0.8288 0.2356 0.058 Uiso 1 1 calc R . . N1B N 0.5347(2) 0.97486(10) 0.77982(7) 0.0432(5) Uani 1 1 d . . . H1B1 H 0.5320 0.9728 0.7360 0.052 Uiso 1 1 calc R . . O1A O 0.3950(2) 1.01331(10) 0.33900(8) 0.0704(6) Uani 1 1 d . . . O2A O 0.44028(19) 1.01898(8) 0.63714(7) 0.0477(4) Uani 1 1 d . . . O3A O 0.60896(17) 0.89288(8) 0.63702(6) 0.0414(4) Uani 1 1 d . . . O1B O 0.4344(2) 0.76545(8) 0.83730(7) 0.0509(4) Uani 1 1 d . . . O2B O 0.4237(2) 0.75882(8) 1.13405(6) 0.0507(4) Uani 1 1 d . . . O3B O 0.59786(17) 0.88167(8) 1.13452(6) 0.0403(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 C1A 0.0402(16) 0.0464(12) 0.0371(10) 0.0035(8) 0.0016(9) 0.0008(10) C2A 0.0520(18) 0.0410(12) 0.0594(13) 0.0039(10) 0.0023(11) 0.0054(11) C3A 0.0502(18) 0.0500(13) 0.0643(14) -0.0190(11) 0.0019(12) 0.0042(11) C4A 0.0434(16) 0.0612(14) 0.0412(11) -0.0160(10) 0.0012(10) -0.0021(11) C5A 0.0337(14) 0.0497(12) 0.0314(9) -0.0028(8) -0.0024(8) -0.0029(10) C6A 0.0550(17) 0.0477(12) 0.0317(9) 0.0047(8) 0.0028(10) 0.0067(11) C7A 0.117(3) 0.0600(16) 0.0741(17) 0.0281(13) 0.0405(18) 0.0260(17) C8A 0.0553(19) 0.0654(15) 0.0386(11) 0.0042(10) -0.0049(11) 0.0186(13) C9A 0.0395(15) 0.0401(11) 0.0333(9) 0.0050(8) -0.0010(9) 0.0009(10) C10A 0.0393(15) 0.0379(11) 0.0417(10) 0.0028(8) 0.0004(9) 0.0084(9) C11A 0.0413(15) 0.0379(10) 0.0331(9) -0.0030(8) 0.0015(9) 0.0005(9) C12A 0.0333(14) 0.0359(10) 0.0284(9) 0.0014(7) -0.0022(8) -0.0012(8) C13A 0.0345(14) 0.0351(10) 0.0315(9) 0.0020(7) 0.0002(8) 0.0045(9) C14A 0.0378(14) 0.0365(11) 0.0289(8) 0.0039(8) 0.0006(8) -0.0010(9) C15A 0.0372(15) 0.0400(11) 0.0287(8) 0.0027(8) -0.0015(9) -0.0006(9) C16A 0.0300(13) 0.0405(10) 0.0291(9) 0.0000(7) 0.0005(8) -0.0037(9) C17A 0.067(2) 0.0497(13) 0.0645(14) -0.0205(12) -0.0078(13) 0.0205(12) C18A 0.0453(17) 0.0598(13) 0.0408(11) 0.0049(10) -0.0067(10) 0.0154(11) C1B 0.0404(14) 0.0354(10) 0.0309(9) 0.0029(7) 0.0017(9) 0.0001(9) C2B 0.0416(16) 0.0340(10) 0.0460(10) 0.0026(8) 0.0016(9) -0.0033(10) C3B 0.0449(16) 0.0383(11) 0.0531(12) 0.0164(9) 0.0003(10) -0.0017(9) C4B 0.0462(16) 0.0514(12) 0.0343(9) 0.0183(9) 0.0009(9) 0.0002(11) C5B 0.0375(14) 0.0413(10) 0.0293(8) 0.0046(7) 0.0038(8) 0.0047(9) C6B 0.0390(14) 0.0395(10) 0.0269(8) -0.0017(7) -0.0011(8) 0.0069(9) C7B 0.0600(18) 0.0511(12) 0.0315(9) -0.0100(9) -0.0029(10) -0.0006(11) C8B 0.0537(18) 0.0467(12) 0.0395(10) -0.0050(9) -0.0049(11) -0.0138(11) C9B 0.0381(14) 0.0328(10) 0.0326(9) -0.0034(7) -0.0014(9) -0.0014(9) C10B 0.0426(15) 0.0329(10) 0.0400(10) 0.0021(8) -0.0023(9) -0.0098(9) C11B 0.0427(15) 0.0339(10) 0.0296(8) 0.0061(7) 0.0004(9) -0.0018(9) C12B 0.0341(14) 0.0304(9) 0.0277(8) 0.0007(7) -0.0024(8) 0.0006(8) C13B 0.0360(13) 0.0273(9) 0.0294(8) 0.0007(7) -0.0011(8) -0.0034(8) C14B 0.0356(14) 0.0267(9) 0.0264(8) -0.0022(7) -0.0005(8) 0.0036(8) C15B 0.0304(13) 0.0320(10) 0.0260(8) 0.0002(7) -0.0016(8) 0.0041(8) C16B 0.0271(13) 0.0345(10) 0.0294(8) 0.0030(7) 0.0000(8) 0.0030(8) C17B 0.085(2) 0.0632(16) 0.0555(14) 0.0237(12) -0.0024(13) -0.0338(15) C18B 0.0603(18) 0.0598(14) 0.0378(11) 0.0036(10) -0.0128(11) -0.0229(12) N1A 0.0599(15) 0.0618(11) 0.0238(7) 0.0039(7) -0.0007(8) 0.0053(10) N1B 0.0572(14) 0.0501(10) 0.0223(7) 0.0022(7) -0.0012(8) 0.0024(9) O1A 0.0971(17) 0.0646(10) 0.0497(9) 0.0248(8) 0.0162(9) 0.0341(11) O2A 0.0530(12) 0.0527(8) 0.0374(7) -0.0126(6) -0.0026(7) 0.0140(8) O3A 0.0453(11) 0.0513(8) 0.0276(6) -0.0013(6) -0.0055(6) 0.0084(7) O1B 0.0757(13) 0.0384(7) 0.0385(7) -0.0108(6) -0.0014(8) -0.0010(8) O2B 0.0634(13) 0.0529(8) 0.0357(7) 0.0147(6) -0.0018(7) -0.0234(8) O3B 0.0498(11) 0.0445(7) 0.0266(6) 0.0052(5) -0.0070(6) -0.0135(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C2A 1.373(3) . ? C1A C16A 1.400(3) . ? C1A H1A 0.9300 . ? C2A C3A 1.402(3) . ? C2A H2A 0.9300 . ? C3A C4A 1.361(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.394(3) . ? C4A H4A 0.9300 . ? C5A N1A 1.367(3) . ? C5A C16A 1.414(2) . ? C6A N1A 1.367(2) . ? C6A C15A 1.372(2) . ? C6A C7A 1.482(3) . ? C7A O1A 1.368(3) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A O1A 1.425(3) . ? C8A C9A 1.501(3) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A C10A 1.396(3) . ? C9A C14A 1.399(3) . ? C10A C11A 1.379(3) . ? C10A H10A 0.9300 . ? C11A O2A 1.375(2) . ? C11A C12A 1.395(3) . ? C12A O3A 1.374(2) . ? C12A C13A 1.381(2) . ? C13A C14A 1.400(3) . ? C13A H13A 0.9300 . ? C14A C15A 1.470(2) . ? C15A C16A 1.433(3) . ? C17A O2A 1.422(3) . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C18A O3A 1.420(2) . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C1B C2B 1.376(3) . ? C1B C16B 1.402(2) . ? C1B H1B 0.9300 . ? C2B C3B 1.391(3) . ? C2B H2B 0.9300 . ? C3B C4B 1.367(3) . ? C3B H3B 0.9300 . ? C4B C5B 1.394(3) . ? C4B H4B 0.9300 . ? C5B N1B 1.372(2) . ? C5B C16B 1.409(2) . ? C6B N1B 1.371(2) . ? C6B C15B 1.379(2) . ? C6B C7B 1.495(3) . ? C7B O1B 1.404(2) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B O1B 1.433(3) . ? C8B C9B 1.498(3) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B C14B 1.390(3) . ? C9B C10B 1.399(3) . ? C10B C11B 1.380(3) . ? C10B H10B 0.9300 . ? C11B O2B 1.368(2) . ? C11B C12B 1.396(3) . ? C12B O3B 1.368(2) . ? C12B C13B 1.380(2) . ? C13B C14B 1.405(2) . ? C13B H13B 0.9300 . ? C14B C15B 1.473(2) . ? C15B C16B 1.450(3) . ? C17B O2B 1.417(3) . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? C18B O3B 1.420(3) . ? C18B H18D 0.9600 . ? C18B H18E 0.9600 . ? C18B H18F 0.9600 . ? N1A H1A1 0.8600 . ? N1B H1B1 0.8600 . ? 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 C2A C1A C16A 119.38(18) . . ? C2A C1A H1A 120.3 . . ? C16A C1A H1A 120.3 . . ? C1A C2A C3A 121.1(2) . . ? C1A C2A H2A 119.5 . . ? C3A C2A H2A 119.5 . . ? C4A C3A C2A 121.5(2) . . ? C4A C3A H3A 119.2 . . ? C2A C3A H3A 119.2 . . ? C3A C4A C5A 117.41(19) . . ? C3A C4A H4A 121.3 . . ? C5A C4A H4A 121.3 . . ? N1A C5A C4A 129.60(17) . . ? N1A C5A C16A 107.73(16) . . ? C4A C5A C16A 122.65(18) . . ? N1A C6A C15A 109.73(17) . . ? N1A C6A C7A 122.23(18) . . ? C15A C6A C7A 127.6(2) . . ? O1A C7A C6A 118.7(2) . . ? O1A C7A H7A1 107.6 . . ? C6A C7A H7A1 107.6 . . ? O1A C7A H7A2 107.6 . . ? C6A C7A H7A2 107.6 . . ? H7A1 C7A H7A2 107.1 . . ? O1A C8A C9A 114.8(2) . . ? O1A C8A H8A1 108.6 . . ? C9A C8A H8A1 108.6 . . ? O1A C8A H8A2 108.6 . . ? C9A C8A H8A2 108.6 . . ? H8A1 C8A H8A2 107.5 . . ? C10A C9A C14A 119.55(18) . . ? C10A C9A C8A 119.51(19) . . ? C14A C9A C8A 120.77(17) . . ? C11A C10A C9A 121.29(19) . . ? C11A C10A H10A 119.4 . . ? C9A C10A H10A 119.4 . . ? O2A C11A C10A 125.20(18) . . ? O2A C11A C12A 115.52(16) . . ? C10A C11A C12A 119.27(16) . . ? O3A C12A C13A 124.51(17) . . ? O3A C12A C11A 115.49(15) . . ? C13A C12A C11A 119.99(16) . . ? C12A C13A C14A 121.12(18) . . ? C12A C13A H13A 119.4 . . ? C14A C13A H13A 119.4 . . ? C9A C14A C13A 118.70(16) . . ? C9A C14A C15A 119.66(16) . . ? C13A C14A C15A 121.64(18) . . ? C6A C15A C16A 106.61(16) . . ? C6A C15A C14A 123.00(17) . . ? C16A C15A C14A 130.38(16) . . ? C1A C16A C5A 117.93(18) . . ? C1A C16A C15A 135.45(16) . . ? C5A C16A C15A 106.59(15) . . ? O2A C17A H17A 109.5 . . ? O2A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? O2A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? O3A C18A H18A 109.5 . . ? O3A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? O3A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C2B C1B C16B 119.42(17) . . ? C2B C1B H1B 120.3 . . ? C16B C1B H1B 120.3 . . ? C1B C2B C3B 121.39(19) . . ? C1B C2B H2B 119.3 . . ? C3B C2B H2B 119.3 . . ? C4B C3B C2B 121.15(18) . . ? C4B C3B H3B 119.4 . . ? C2B C3B H3B 119.4 . . ? C3B C4B C5B 117.64(17) . . ? C3B C4B H4B 121.2 . . ? C5B C4B H4B 121.2 . . ? N1B C5B C4B 129.85(16) . . ? N1B C5B C16B 107.42(16) . . ? C4B C5B C16B 122.67(18) . . ? N1B C6B C15B 109.68(16) . . ? N1B C6B C7B 117.63(15) . . ? C15B C6B C7B 132.68(17) . . ? O1B C7B C6B 114.62(15) . . ? O1B C7B H7B1 108.6 . . ? C6B C7B H7B1 108.6 . . ? O1B C7B H7B2 108.6 . . ? C6B C7B H7B2 108.6 . . ? H7B1 C7B H7B2 107.6 . . ? O1B C8B C9B 110.7(2) . . ? O1B C8B H8B1 109.5 . . ? C9B C8B H8B1 109.5 . . ? O1B C8B H8B2 109.5 . . ? C9B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 108.1 . . ? C14B C9B C10B 119.97(17) . . ? C14B C9B C8B 120.33(17) . . ? C10B C9B C8B 119.69(18) . . ? C11B C10B C9B 121.40(18) . . ? C11B C10B H10B 119.3 . . ? C9B C10B H10B 119.3 . . ? O2B C11B C10B 125.44(18) . . ? O2B C11B C12B 115.66(16) . . ? C10B C11B C12B 118.90(16) . . ? O3B C12B C13B 124.86(17) . . ? O3B C12B C11B 115.19(15) . . ? C13B C12B C11B 119.94(16) . . ? C12B C13B C14B 121.54(18) . . ? C12B C13B H13B 119.2 . . ? C14B C13B H13B 119.2 . . ? C9B C14B C13B 118.17(15) . . ? C9B C14B C15B 121.84(16) . . ? C13B C14B C15B 119.98(17) . . ? C6B C15B C16B 105.96(15) . . ? C6B C15B C14B 127.37(16) . . ? C16B C15B C14B 126.43(15) . . ? C1B C16B C5B 117.72(16) . . ? C1B C16B C15B 134.97(16) . . ? C5B C16B C15B 107.14(15) . . ? O2B C17B H17D 109.5 . . ? O2B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? O2B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? O3B C18B H18D 109.5 . . ? O3B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? O3B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C6A N1A C5A 109.30(15) . . ? C6A N1A H1A1 125.3 . . ? C5A N1A H1A1 125.3 . . ? C6B N1B C5B 109.79(14) . . ? C6B N1B H1B1 125.1 . . ? C5B N1B H1B1 125.1 . . ? C7A O1A C8A 117.30(18) . . ? C11A O2A C17A 117.48(16) . . ? C12A O3A C18A 117.40(14) . . ? C7B O1B C8B 112.97(16) . . ? C11B O2B C17B 117.25(16) . . ? C12B O3B C18B 117.32(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 C16A C1A C2A C3A -0.3(4) . . . . ? C1A C2A C3A C4A -0.4(4) . . . . ? C2A C3A C4A C5A 1.1(4) . . . . ? C3A C4A C5A N1A 176.9(3) . . . . ? C3A C4A C5A C16A -1.2(4) . . . . ? N1A C6A C7A O1A 131.5(3) . . . . ? C15A C6A C7A O1A -57.2(5) . . . . ? O1A C8A C9A C10A 110.9(2) . . . . ? O1A C8A C9A C14A -73.8(3) . . . . ? C14A C9A C10A C11A -3.2(3) . . . . ? C8A C9A C10A C11A 172.2(2) . . . . ? C9A C10A C11A O2A -178.05(19) . . . . ? C9A C10A C11A C12A 1.8(4) . . . . ? O2A C11A C12A O3A -0.3(3) . . . . ? C10A C11A C12A O3A 179.8(2) . . . . ? O2A C11A C12A C13A -179.45(18) . . . . ? C10A C11A C12A C13A 0.7(3) . . . . ? O3A C12A C13A C14A 179.2(2) . . . . ? C11A C12A C13A C14A -1.8(3) . . . . ? C10A C9A C14A C13A 2.1(3) . . . . ? C8A C9A C14A C13A -173.2(2) . . . . ? C10A C9A C14A C15A -178.14(19) . . . . ? C8A C9A C14A C15A 6.6(3) . . . . ? C12A C13A C14A C9A 0.4(3) . . . . ? C12A C13A C14A C15A -179.41(18) . . . . ? N1A C6A C15A C16A 1.8(3) . . . . ? C7A C6A C15A C16A -170.4(3) . . . . ? N1A C6A C15A C14A -177.4(2) . . . . ? C7A C6A C15A C14A 10.4(4) . . . . ? C9A C14A C15A C6A 30.4(3) . . . . ? C13A C14A C15A C6A -149.8(2) . . . . ? C9A C14A C15A C16A -148.6(2) . . . . ? C13A C14A C15A C16A 31.2(4) . . . . ? C2A C1A C16A C5A 0.3(3) . . . . ? C2A C1A C16A C15A -177.2(3) . . . . ? N1A C5A C16A C1A -178.0(2) . . . . ? C4A C5A C16A C1A 0.5(3) . . . . ? N1A C5A C16A C15A 0.2(3) . . . . ? C4A C5A C16A C15A 178.6(2) . . . . ? C6A C15A C16A C1A 176.5(3) . . . . ? C14A C15A C16A C1A -4.4(4) . . . . ? C6A C15A C16A C5A -1.2(2) . . . . ? C14A C15A C16A C5A 178.0(2) . . . . ? C16B C1B C2B C3B 0.1(4) . . . . ? C1B C2B C3B C4B 0.6(4) . . . . ? C2B C3B C4B C5B -0.4(4) . . . . ? C3B C4B C5B N1B 176.4(2) . . . . ? C3B C4B C5B C16B -0.5(4) . . . . ? N1B C6B C7B O1B -174.5(2) . . . . ? C15B C6B C7B O1B 3.9(4) . . . . ? O1B C8B C9B C14B 61.8(3) . . . . ? O1B C8B C9B C10B -116.9(2) . . . . ? C14B C9B C10B C11B 0.9(3) . . . . ? C8B C9B C10B C11B 179.6(2) . . . . ? C9B C10B C11B O2B 178.8(2) . . . . ? C9B C10B C11B C12B -0.6(3) . . . . ? O2B C11B C12B O3B -0.2(3) . . . . ? C10B C11B C12B O3B 179.25(19) . . . . ? O2B C11B C12B C13B 179.08(19) . . . . ? C10B C11B C12B C13B -1.5(3) . . . . ? O3B C12B C13B C14B -177.54(18) . . . . ? C11B C12B C13B C14B 3.2(3) . . . . ? C10B C9B C14B C13B 0.8(3) . . . . ? C8B C9B C14B C13B -177.9(2) . . . . ? C10B C9B C14B C15B -177.60(18) . . . . ? C8B C9B C14B C15B 3.7(3) . . . . ? C12B C13B C14B C9B -2.9(3) . . . . ? C12B C13B C14B C15B 175.57(17) . . . . ? N1B C6B C15B C16B 0.8(2) . . . . ? C7B C6B C15B C16B -177.7(2) . . . . ? N1B C6B C15B C14B 175.5(2) . . . . ? C7B C6B C15B C14B -3.0(4) . . . . ? C9B C14B C15B C6B -25.9(3) . . . . ? C13B C14B C15B C6B 155.7(2) . . . . ? C9B C14B C15B C16B 147.8(2) . . . . ? C13B C14B C15B C16B -30.6(3) . . . . ? C2B C1B C16B C5B -1.0(3) . . . . ? C2B C1B C16B C15B -175.5(2) . . . . ? N1B C5B C16B C1B -176.23(19) . . . . ? C4B C5B C16B C1B 1.2(3) . . . . ? N1B C5B C16B C15B -0.4(2) . . . . ? C4B C5B C16B C15B 177.1(2) . . . . ? C6B C15B C16B C1B 174.6(2) . . . . ? C14B C15B C16B C1B -0.2(4) . . . . ? C6B C15B C16B C5B -0.3(2) . . . . ? C14B C15B C16B C5B -175.0(2) . . . . ? C15A C6A N1A C5A -1.7(3) . . . . ? C7A C6A N1A C5A 170.9(3) . . . . ? C4A C5A N1A C6A -177.4(3) . . . . ? C16A C5A N1A C6A 0.9(3) . . . . ? C15B C6B N1B C5B -1.1(3) . . . . ? C7B C6B N1B C5B 177.6(2) . . . . ? C4B C5B N1B C6B -176.3(2) . . . . ? C16B C5B N1B C6B 0.9(2) . . . . ? C6A C7A O1A C8A 15.4(4) . . . . ? C9A C8A O1A C7A 59.1(3) . . . . ? C10A C11A O2A C17A -0.4(3) . . . . ? C12A C11A O2A C17A 179.7(2) . . . . ? C13A C12A O3A C18A 5.7(3) . . . . ? C11A C12A O3A C18A -173.34(19) . . . . ? C6B C7B O1B C8B 49.8(3) . . . . ? C9B C8B O1B C7B -96.6(2) . . . . ? C10B C11B O2B C17B 2.3(3) . . . . ? C12B C11B O2B C17B -178.3(2) . . . . ? C13B C12B O3B C18B -1.3(3) . . . . ? C11B C12B O3B C18B 178.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.146 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.031 _vrf_PLAT029_new ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.906 RESPONSE: : Even though crystal data was collected up to 0.73 \%A resolution, the crystal (the largest available) still diffracted quite weakly at high angle. On repeated recrystallisation we could get only small sized crystals. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 884176'