# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Karl Wallace' _publ_contact_author_address ; Chemistry and Biochemistry University of Texas at Austin Austin 78712 UNITED STATES OF AMERICA ; _publ_contact_author_email KARLWALLACE2003@YAHOO.COM _publ_section_title ; Detection of Chemical Warfare Simulants by Phosphorylation of a Coumarin Oximate ; loop_ _publ_author_name 'Karl Wallace' 'Eric V. Anslyn' 'Ruth I. Fagbemi' 'Frantz J. Folmer-Andersen' ; V.M.Lynch ; 'Jeroni Morey' # Attachment 'X-Ray for 2a1.CIF' data_kw16 _database_code_depnum_ccdc_archive 'CCDC 614391' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 N2 O3' _chemical_formula_weight 316.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 14.9783(4) _cell_length_b 16.9346(6) _cell_length_c 13.5481(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.484(2) _cell_angle_gamma 90.00 _cell_volume 3389.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 423(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lathes _exptl_crystal_colour orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.085 _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 -117(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 'Nonius Kappa CCD' _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 10984 _diffrn_reflns_av_R_equivalents 0.1388 _diffrn_reflns_av_sigmaI/netI 0.2229 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5895 _reflns_number_gt 2259 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0200P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5895 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2382 _refine_ls_R_factor_gt 0.0786 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.011 _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 O1' O 0.59068(18) 0.43505(18) 0.56675(19) 0.0350(8) Uani 1 1 d . . . C2' C 0.5672(3) 0.3684(3) 0.5115(3) 0.0342(12) Uani 1 1 d . . . C3' C 0.5786(3) 0.3679(3) 0.4079(3) 0.0313(11) Uani 1 1 d . . . C4' C 0.6093(3) 0.4331(3) 0.3643(3) 0.0325(12) Uani 1 1 d . . . C5' C 0.6313(3) 0.5020(3) 0.4241(3) 0.0300(11) Uani 1 1 d . . . C6' C 0.6618(3) 0.5746(3) 0.3907(3) 0.0388(12) Uani 1 1 d . . . H6' H 0.6687 0.5792 0.3217 0.047 Uiso 1 1 d R . . C7' C 0.6811(3) 0.6383(3) 0.4520(3) 0.0397(12) Uani 1 1 d . . . H7' H 0.7005 0.6870 0.4261 0.048 Uiso 1 1 d R . . C8' C 0.6726(3) 0.6347(3) 0.5551(3) 0.0387(12) Uani 1 1 d . . . C9' C 0.6411(3) 0.5638(3) 0.5894(3) 0.0340(11) Uani 1 1 d . . . H9' H 0.6340 0.5583 0.6582 0.041 Uiso 1 1 d R . . C10' C 0.6220(3) 0.5025(3) 0.5247(3) 0.0330(11) Uani 1 1 d . . . O11' O 0.53855(19) 0.31400(18) 0.5574(2) 0.0414(8) Uani 1 1 d . . . C12' C 0.5524(3) 0.2908(3) 0.3616(3) 0.0412(13) Uani 1 1 d . . . H12' H 0.5312 0.2509 0.4025 0.049 Uiso 1 1 d R . . N13' N 0.5552(2) 0.2731(2) 0.2703(3) 0.0439(10) Uani 1 1 d . . . O14' O 0.5223(2) 0.1957(2) 0.2507(2) 0.0551(10) Uani 1 1 d . . . C15' C 0.6192(3) 0.4328(3) 0.2558(3) 0.0452(13) Uani 1 1 d . . . H15C H 0.6483 0.3844 0.2420 0.054 Uiso 1 1 d R . . H15D H 0.6571 0.4758 0.2422 0.054 Uiso 1 1 d R . . C16' C 0.5295(4) 0.4412(3) 0.1857(4) 0.0735(18) Uani 1 1 d . . . H16C H 0.4883 0.4028 0.2049 0.088 Uiso 1 1 d R . . H16D H 0.5368 0.4306 0.1179 0.088 Uiso 1 1 d R . . C17' C 0.4886(4) 0.5173(3) 0.1888(4) 0.0719(17) Uani 1 1 d . . . H17C H 0.5316 0.5557 0.1737 0.086 Uiso 1 1 d R . . H17D H 0.4780 0.5266 0.2558 0.086 Uiso 1 1 d R . . C18' C 0.3954(4) 0.5275(3) 0.1137(4) 0.090(2) Uani 1 1 d . . . H18D H 0.3718 0.5798 0.1189 0.135 Uiso 1 1 d R . . H18E H 0.4064 0.5188 0.0467 0.135 Uiso 1 1 d R . . H18F H 0.3523 0.4895 0.1295 0.135 Uiso 1 1 d R . . N19' N 0.6934(2) 0.6982(2) 0.6172(3) 0.0459(10) Uani 1 1 d . . . C20' C 0.6860(3) 0.6937(3) 0.7236(3) 0.0504(14) Uani 1 1 d . . . H20C H 0.6313 0.6665 0.7314 0.060 Uiso 1 1 d R . . H20D H 0.6825 0.7465 0.7484 0.060 Uiso 1 1 d R . . C21' C 0.7661(3) 0.6531(3) 0.7867(3) 0.0614(16) Uani 1 1 d . . . H21D H 0.7599 0.6518 0.8561 0.092 Uiso 1 1 d R . . H21E H 0.7690 0.6001 0.7623 0.092 Uiso 1 1 d R . . H21F H 0.8206 0.6807 0.7794 0.092 Uiso 1 1 d R . . C22' C 0.7261(3) 0.7731(3) 0.5840(3) 0.0502(14) Uani 1 1 d . . . H22C H 0.7624 0.7637 0.5330 0.060 Uiso 1 1 d R . . H22D H 0.7636 0.7978 0.6397 0.060 Uiso 1 1 d R . . C23' C 0.6496(3) 0.8301(3) 0.5441(4) 0.0653(16) Uani 1 1 d . . . H23D H 0.6731 0.8790 0.5235 0.098 Uiso 1 1 d R . . H23E H 0.6126 0.8056 0.4877 0.098 Uiso 1 1 d R . . H23F H 0.6138 0.8400 0.5954 0.098 Uiso 1 1 d R . . O1 O 0.88300(18) 0.57744(18) 0.56072(19) 0.0353(8) Uani 1 1 d . . . C2 C 0.9096(3) 0.6368(3) 0.5020(3) 0.0372(12) Uani 1 1 d . . . C3 C 0.9260(3) 0.6170(3) 0.4033(3) 0.0319(11) Uani 1 1 d . . . C4 C 0.9170(3) 0.5412(3) 0.3687(3) 0.0336(12) Uani 1 1 d . . . C5 C 0.8869(3) 0.4813(3) 0.4310(3) 0.0326(12) Uani 1 1 d . . . C6 C 0.8729(3) 0.4010(3) 0.4066(3) 0.0406(13) Uani 1 1 d . . . H6 H 0.8854 0.3837 0.3427 0.049 Uiso 1 1 d R . . C7 C 0.8431(3) 0.3472(3) 0.4685(3) 0.0388(13) Uani 1 1 d . . . H7 H 0.8337 0.2932 0.4480 0.047 Uiso 1 1 d R . . C8 C 0.8251(3) 0.3701(3) 0.5631(3) 0.0395(12) Uani 1 1 d . . . C9 C 0.8385(3) 0.4496(3) 0.5898(3) 0.0352(12) Uani 1 1 d . . . H9 H 0.8266 0.4674 0.6535 0.042 Uiso 1 1 d R . . C10 C 0.8680(3) 0.5018(3) 0.5243(3) 0.0307(11) Uani 1 1 d . . . O11 O 0.9191(2) 0.70246(18) 0.5401(2) 0.0451(9) Uani 1 1 d . . . C12 C 0.9561(3) 0.6863(3) 0.3525(3) 0.0386(12) Uani 1 1 d . . . H12 H 0.9886 0.7268 0.3931 0.046 Uiso 1 1 d R . . N13 N 0.9420(2) 0.6958(2) 0.2571(3) 0.0411(10) Uani 1 1 d . . . O14 O 0.9798(2) 0.7691(2) 0.2336(3) 0.0483(9) Uani 1 1 d . . . C15 C 0.9362(3) 0.5182(2) 0.2661(3) 0.0350(12) Uani 1 1 d . . . H15A H 0.9648 0.4673 0.2687 0.042 Uiso 1 1 d R . . H15B H 0.9771 0.5563 0.2458 0.042 Uiso 1 1 d R . . C16 C 0.8501(3) 0.5168(3) 0.1865(3) 0.0450(13) Uani 1 1 d . . . H16A H 0.8195 0.5665 0.1873 0.054 Uiso 1 1 d R . . H16B H 0.8110 0.4763 0.2045 0.054 Uiso 1 1 d R . . C17 C 0.8691(3) 0.5024(3) 0.0808(3) 0.0543(14) Uani 1 1 d . . . H17A H 0.8134 0.4912 0.0370 0.065 Uiso 1 1 d R . . H17B H 0.9070 0.4565 0.0826 0.065 Uiso 1 1 d R . . C18 C 0.9163(3) 0.5692(3) 0.0369(3) 0.0631(16) Uani 1 1 d . . . H18A H 0.9274 0.5562 -0.0290 0.095 Uiso 1 1 d R . . H18B H 0.8781 0.6150 0.0335 0.095 Uiso 1 1 d R . . H18C H 0.9727 0.5800 0.0796 0.095 Uiso 1 1 d R . . N19 N 0.7947(2) 0.3176(2) 0.6277(2) 0.0420(10) Uani 1 1 d . . . C20 C 0.7617(3) 0.3421(3) 0.7181(3) 0.0474(13) Uani 1 1 d . . . H20A H 0.7191 0.3038 0.7343 0.057 Uiso 1 1 d R . . H20B H 0.7307 0.3916 0.7053 0.057 Uiso 1 1 d R . . C21 C 0.8367(3) 0.3524(3) 0.8083(3) 0.0570(15) Uani 1 1 d . . . H21A H 0.8124 0.3690 0.8662 0.085 Uiso 1 1 d R . . H21B H 0.8672 0.3028 0.8217 0.085 Uiso 1 1 d R . . H21C H 0.8789 0.3913 0.7925 0.085 Uiso 1 1 d R . . C22 C 0.8028(3) 0.2304(3) 0.6131(4) 0.0537(14) Uani 1 1 d . . . H22A H 0.8165 0.2053 0.6774 0.064 Uiso 1 1 d R . . H22B H 0.8519 0.2202 0.5774 0.064 Uiso 1 1 d R . . C23 C 0.7176(3) 0.1957(3) 0.5569(4) 0.0650(16) Uani 1 1 d . . . H23A H 0.7245 0.1398 0.5487 0.097 Uiso 1 1 d R . . H23B H 0.6687 0.2053 0.5931 0.097 Uiso 1 1 d R . . H23C H 0.7045 0.2203 0.4923 0.097 Uiso 1 1 d R . . H14' H 0.522(3) 0.190(3) 0.180(4) 0.085(18) Uiso 1 1 d . . . H14 H 0.952(4) 0.777(4) 0.166(5) 0.15(3) 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 O1' 0.039(2) 0.035(2) 0.0306(18) -0.0008(17) 0.0060(15) 0.0019(16) C2' 0.027(3) 0.034(3) 0.041(3) -0.001(3) 0.006(2) 0.005(2) C3' 0.031(3) 0.039(3) 0.023(3) -0.001(2) 0.002(2) 0.001(2) C4' 0.027(3) 0.049(3) 0.023(3) -0.001(3) 0.006(2) 0.001(2) C5' 0.022(3) 0.042(3) 0.027(3) 0.000(3) 0.007(2) 0.002(2) C6' 0.036(3) 0.050(3) 0.033(3) -0.001(3) 0.013(2) 0.000(3) C7' 0.039(3) 0.040(3) 0.040(3) 0.010(3) 0.005(2) 0.001(3) C8' 0.028(3) 0.044(4) 0.042(3) -0.004(3) 0.000(2) 0.005(3) C9' 0.036(3) 0.031(3) 0.036(3) -0.004(3) 0.009(2) -0.003(2) C10' 0.030(3) 0.031(3) 0.039(3) 0.006(3) 0.008(2) 0.006(2) O11' 0.049(2) 0.042(2) 0.0343(19) -0.0011(17) 0.0087(16) -0.0007(17) C12' 0.040(3) 0.052(4) 0.032(3) -0.002(3) 0.006(2) -0.001(3) N13' 0.055(3) 0.044(3) 0.034(3) -0.006(2) 0.010(2) -0.002(2) O14' 0.083(3) 0.045(2) 0.041(2) -0.010(2) 0.020(2) -0.012(2) C15' 0.045(3) 0.060(4) 0.030(3) 0.004(3) 0.004(3) -0.007(3) C16' 0.099(5) 0.075(5) 0.046(4) 0.012(4) 0.010(4) -0.013(4) C17' 0.074(4) 0.066(5) 0.078(4) -0.002(4) 0.022(4) 0.000(4) C18' 0.069(4) 0.064(5) 0.124(6) 0.000(4) -0.023(4) 0.005(3) N19' 0.052(3) 0.043(3) 0.044(3) 0.001(2) 0.010(2) 0.000(2) C20' 0.063(4) 0.049(3) 0.041(3) -0.008(3) 0.013(3) -0.005(3) C21' 0.055(4) 0.083(4) 0.042(3) -0.008(3) -0.004(3) -0.016(3) C22' 0.057(3) 0.040(3) 0.056(3) -0.005(3) 0.018(3) -0.014(3) C23' 0.059(4) 0.051(4) 0.090(4) 0.012(3) 0.025(3) 0.000(3) O1 0.0363(19) 0.039(2) 0.0306(18) -0.0012(17) 0.0072(15) 0.0088(16) C2 0.035(3) 0.037(3) 0.038(3) 0.011(3) 0.002(2) 0.005(3) C3 0.031(3) 0.032(3) 0.032(3) -0.002(3) 0.004(2) 0.002(2) C4 0.031(3) 0.044(3) 0.026(3) 0.008(2) 0.004(2) 0.007(2) C5 0.032(3) 0.035(3) 0.030(3) -0.001(3) 0.003(2) 0.006(2) C6 0.037(3) 0.051(4) 0.036(3) -0.005(3) 0.014(2) 0.004(3) C7 0.042(3) 0.036(3) 0.041(3) -0.004(2) 0.013(3) -0.005(2) C8 0.036(3) 0.041(4) 0.043(3) 0.003(3) 0.012(3) -0.001(3) C9 0.033(3) 0.044(3) 0.030(3) 0.002(3) 0.007(2) 0.006(2) C10 0.028(3) 0.028(3) 0.035(3) -0.002(3) 0.002(2) 0.002(2) O11 0.062(2) 0.036(2) 0.038(2) -0.0038(17) 0.0099(17) 0.0040(18) C12 0.038(3) 0.039(3) 0.038(3) 0.000(3) 0.003(2) -0.001(3) N13 0.045(3) 0.036(3) 0.043(3) 0.007(2) 0.010(2) -0.001(2) O14 0.052(2) 0.046(2) 0.047(2) 0.0112(19) 0.0071(19) -0.0031(18) C15 0.036(3) 0.037(3) 0.036(3) -0.004(2) 0.014(2) 0.001(2) C16 0.052(3) 0.061(4) 0.020(3) -0.004(2) 0.001(2) 0.000(3) C17 0.060(4) 0.060(4) 0.045(3) -0.003(3) 0.013(3) -0.012(3) C18 0.061(4) 0.088(4) 0.042(3) -0.006(3) 0.015(3) 0.006(3) N19 0.050(3) 0.039(3) 0.038(2) -0.002(2) 0.009(2) -0.002(2) C20 0.039(3) 0.057(4) 0.050(3) 0.004(3) 0.017(3) -0.004(3) C21 0.053(3) 0.072(4) 0.046(3) 0.008(3) 0.008(3) 0.005(3) C22 0.056(4) 0.051(4) 0.054(3) 0.008(3) 0.010(3) -0.011(3) C23 0.055(4) 0.063(4) 0.078(4) 0.004(3) 0.016(3) -0.001(3) _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 O1' C2' 1.368(5) . ? O1' C10' 1.391(5) . ? C2' O11' 1.229(5) . ? C2' C3' 1.440(5) . ? C3' C4' 1.367(5) . ? C3' C12' 1.473(6) . ? C4' C5' 1.428(5) . ? C4' C15' 1.502(5) . ? C5' C10' 1.394(5) . ? C5' C6' 1.411(6) . ? C6' C7' 1.363(5) . ? C6' H6' 0.9601 . ? C7' C8' 1.425(5) . ? C7' H7' 0.9598 . ? C8' N19' 1.369(5) . ? C8' C9' 1.398(5) . ? C9' C10' 1.357(5) . ? C9' H9' 0.9600 . ? C12' N13' 1.280(5) . ? C12' H12' 0.9599 . ? N13' O14' 1.410(4) . ? O14' H14' 0.95(5) . ? C15' C16' 1.519(6) . ? C15' H15C 0.9600 . ? C15' H15D 0.9601 . ? C16' C17' 1.431(6) . ? C16' H16C 0.9600 . ? C16' H16D 0.9600 . ? C17' C18' 1.595(6) . ? C17' H17C 0.9600 . ? C17' H17D 0.9600 . ? C18' H18D 0.9599 . ? C18' H18E 0.9599 . ? C18' H18F 0.9600 . ? N19' C22' 1.457(5) . ? N19' C20' 1.466(5) . ? C20' C21' 1.519(6) . ? C20' H20C 0.9600 . ? C20' H20D 0.9600 . ? C21' H21D 0.9600 . ? C21' H21E 0.9600 . ? C21' H21F 0.9601 . ? C22' C23' 1.527(6) . ? C22' H22C 0.9601 . ? C22' H22D 0.9600 . ? C23' H23D 0.9600 . ? C23' H23E 0.9601 . ? C23' H23F 0.9601 . ? O1 C10 1.378(5) . ? O1 C2 1.380(5) . ? C2 O11 1.225(5) . ? C2 C3 1.439(6) . ? C3 C4 1.365(5) . ? C3 C12 1.468(6) . ? C4 C5 1.439(5) . ? C4 C15 1.516(5) . ? C5 C10 1.384(5) . ? C5 C6 1.407(5) . ? C6 C7 1.363(5) . ? C6 H6 0.9600 . ? C7 C8 1.407(5) . ? C7 H7 0.9600 . ? C8 N19 1.377(5) . ? C8 C9 1.399(5) . ? C9 C10 1.375(5) . ? C9 H9 0.9600 . ? C12 N13 1.285(5) . ? C12 H12 0.9601 . ? N13 O14 1.422(4) . ? O14 H14 0.96(6) . ? C15 C16 1.539(5) . ? C15 H15A 0.9599 . ? C15 H15B 0.9599 . ? C16 C17 1.524(5) . ? C16 H16A 0.9599 . ? C16 H16B 0.9602 . ? C17 C18 1.507(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9598 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N19 C20 1.456(5) . ? N19 C22 1.497(5) . ? C20 C21 1.527(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9599 . ? C21 H21A 0.9599 . ? C21 H21B 0.9598 . ? C21 H21C 0.9602 . ? C22 C23 1.495(6) . ? C22 H22A 0.9600 . ? C22 H22B 0.9601 . ? C23 H23A 0.9599 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2' O1' C10' 121.8(3) . . ? O11' C2' O1' 114.9(4) . . ? O11' C2' C3' 126.6(4) . . ? O1' C2' C3' 118.5(4) . . ? C4' C3' C2' 121.2(4) . . ? C4' C3' C12' 128.0(4) . . ? C2' C3' C12' 110.8(4) . . ? C3' C4' C5' 118.5(4) . . ? C3' C4' C15' 121.0(4) . . ? C5' C4' C15' 120.5(4) . . ? C10' C5' C6' 113.5(4) . . ? C10' C5' C4' 120.6(4) . . ? C6' C5' C4' 126.0(4) . . ? C7' C6' C5' 122.8(4) . . ? C7' C6' H6' 118.9 . . ? C5' C6' H6' 118.3 . . ? C6' C7' C8' 121.3(4) . . ? C6' C7' H7' 120.2 . . ? C8' C7' H7' 118.4 . . ? N19' C8' C9' 121.7(4) . . ? N19' C8' C7' 121.4(4) . . ? C9' C8' C7' 116.8(4) . . ? C10' C9' C8' 119.3(4) . . ? C10' C9' H9' 120.5 . . ? C8' C9' H9' 120.2 . . ? C9' C10' O1' 114.4(4) . . ? C9' C10' C5' 126.2(4) . . ? O1' C10' C5' 119.4(4) . . ? N13' C12' C3' 124.8(4) . . ? N13' C12' H12' 117.3 . . ? C3' C12' H12' 117.9 . . ? C12' N13' O14' 109.5(4) . . ? N13' O14' H14' 103(3) . . ? C4' C15' C16' 113.1(4) . . ? C4' C15' H15C 108.3 . . ? C16' C15' H15C 110.0 . . ? C4' C15' H15D 110.0 . . ? C16' C15' H15D 107.4 . . ? H15C C15' H15D 107.9 . . ? C17' C16' C15' 113.9(5) . . ? C17' C16' H16C 107.7 . . ? C15' C16' H16C 108.0 . . ? C17' C16' H16D 108.3 . . ? C15' C16' H16D 110.6 . . ? H16C C16' H16D 108.3 . . ? C16' C17' C18' 114.3(5) . . ? C16' C17' H17C 107.4 . . ? C18' C17' H17C 109.8 . . ? C16' C17' H17D 108.3 . . ? C18' C17' H17D 108.7 . . ? H17C C17' H17D 108.2 . . ? C17' C18' H18D 110.3 . . ? C17' C18' H18E 108.5 . . ? H18D C18' H18E 109.5 . . ? C17' C18' H18F 109.6 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? C8' N19' C22' 123.2(4) . . ? C8' N19' C20' 121.1(4) . . ? C22' N19' C20' 115.7(4) . . ? N19' C20' C21' 113.3(4) . . ? N19' C20' H20C 109.7 . . ? C21' C20' H20C 109.3 . . ? N19' C20' H20D 108.2 . . ? C21' C20' H20D 108.0 . . ? H20C C20' H20D 108.2 . . ? C20' C21' H21D 111.5 . . ? C20' C21' H21E 107.8 . . ? H21D C21' H21E 109.5 . . ? C20' C21' H21F 109.1 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? N19' C22' C23' 112.9(4) . . ? N19' C22' H22C 109.7 . . ? C23' C22' H22C 109.3 . . ? N19' C22' H22D 108.7 . . ? C23' C22' H22D 108.1 . . ? H22C C22' H22D 108.1 . . ? C22' C23' H23D 111.1 . . ? C22' C23' H23E 108.0 . . ? H23D C23' H23E 109.5 . . ? C22' C23' H23F 109.3 . . ? H23D C23' H23F 109.5 . . ? H23E C23' H23F 109.5 . . ? C10 O1 C2 121.1(3) . . ? O11 C2 O1 116.3(4) . . ? O11 C2 C3 125.3(4) . . ? O1 C2 C3 118.4(4) . . ? C4 C3 C2 121.0(4) . . ? C4 C3 C12 127.7(4) . . ? C2 C3 C12 111.2(4) . . ? C3 C4 C5 119.0(4) . . ? C3 C4 C15 122.2(4) . . ? C5 C4 C15 118.8(4) . . ? C10 C5 C6 114.4(4) . . ? C10 C5 C4 119.3(4) . . ? C6 C5 C4 126.3(4) . . ? C7 C6 C5 123.5(4) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 117.6 . . ? C6 C7 C8 120.6(4) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 119.0 . . ? N19 C8 C9 120.4(4) . . ? N19 C8 C7 122.2(4) . . ? C9 C8 C7 117.3(4) . . ? C10 C9 C8 120.0(4) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 119.7 . . ? C9 C10 O1 114.7(4) . . ? C9 C10 C5 124.3(4) . . ? O1 C10 C5 120.9(4) . . ? N13 C12 C3 124.0(4) . . ? N13 C12 H12 118.1 . . ? C3 C12 H12 117.9 . . ? C12 N13 O14 109.1(4) . . ? N13 O14 H14 102(4) . . ? C4 C15 C16 112.5(3) . . ? C4 C15 H15A 110.3 . . ? C16 C15 H15A 109.2 . . ? C4 C15 H15B 108.4 . . ? C16 C15 H15B 108.1 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 113.4(4) . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 109.9 . . ? C15 C16 H16B 108.0 . . ? H16A C16 H16B 108.1 . . ? C18 C17 C16 115.0(4) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17B 107.7 . . ? C16 C17 H17B 107.8 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 111.1 . . ? C17 C18 H18B 108.1 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.2 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 N19 C20 122.9(4) . . ? C8 N19 C22 120.8(4) . . ? C20 N19 C22 116.0(4) . . ? N19 C20 C21 113.5(3) . . ? N19 C20 H20A 109.2 . . ? C21 C20 H20A 108.9 . . ? N19 C20 H20B 108.6 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 108.0 . . ? C20 C21 H21A 111.0 . . ? C20 C21 H21B 108.4 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 108.9 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 N19 112.0(4) . . ? C23 C22 H22A 109.0 . . ? N19 C22 H22A 109.0 . . ? C23 C22 H22B 109.4 . . ? N19 C22 H22B 109.2 . . ? H22A C22 H22B 108.1 . . ? C22 C23 H23A 110.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 108.8 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10' O1' C2' O11' -178.2(3) . . . . ? C10' O1' C2' C3' 2.3(6) . . . . ? O11' C2' C3' C4' 178.5(4) . . . . ? O1' C2' C3' C4' -2.1(6) . . . . ? O11' C2' C3' C12' -1.0(6) . . . . ? O1' C2' C3' C12' 178.4(3) . . . . ? C2' C3' C4' C5' 0.8(6) . . . . ? C12' C3' C4' C5' -179.7(4) . . . . ? C2' C3' C4' C15' -178.7(4) . . . . ? C12' C3' C4' C15' 0.8(7) . . . . ? C3' C4' C5' C10' 0.3(6) . . . . ? C15' C4' C5' C10' 179.8(4) . . . . ? C3' C4' C5' C6' -178.4(4) . . . . ? C15' C4' C5' C6' 1.1(6) . . . . ? C10' C5' C6' C7' 0.8(6) . . . . ? C4' C5' C6' C7' 179.6(4) . . . . ? C5' C6' C7' C8' 0.9(7) . . . . ? C6' C7' C8' N19' 178.9(4) . . . . ? C6' C7' C8' C9' -1.9(6) . . . . ? N19' C8' C9' C10' -179.6(4) . . . . ? C7' C8' C9' C10' 1.2(6) . . . . ? C8' C9' C10' O1' -179.7(4) . . . . ? C8' C9' C10' C5' 0.6(7) . . . . ? C2' O1' C10' C9' 179.1(4) . . . . ? C2' O1' C10' C5' -1.2(6) . . . . ? C6' C5' C10' C9' -1.6(6) . . . . ? C4' C5' C10' C9' 179.5(4) . . . . ? C6' C5' C10' O1' 178.7(3) . . . . ? C4' C5' C10' O1' -0.1(6) . . . . ? C4' C3' C12' N13' 0.4(7) . . . . ? C2' C3' C12' N13' 179.9(4) . . . . ? C3' C12' N13' O14' -177.9(4) . . . . ? C3' C4' C15' C16' 76.6(6) . . . . ? C5' C4' C15' C16' -102.9(5) . . . . ? C4' C15' C16' C17' 69.0(6) . . . . ? C15' C16' C17' C18' 178.7(4) . . . . ? C9' C8' N19' C22' -179.8(4) . . . . ? C7' C8' N19' C22' -0.7(7) . . . . ? C9' C8' N19' C20' 1.9(7) . . . . ? C7' C8' N19' C20' -179.0(4) . . . . ? C8' N19' C20' C21' 80.0(5) . . . . ? C22' N19' C20' C21' -98.5(5) . . . . ? C8' N19' C22' C23' 88.9(5) . . . . ? C20' N19' C22' C23' -92.7(5) . . . . ? C10 O1 C2 O11 178.2(4) . . . . ? C10 O1 C2 C3 -3.1(5) . . . . ? O11 C2 C3 C4 177.4(4) . . . . ? O1 C2 C3 C4 -1.1(6) . . . . ? O11 C2 C3 C12 0.1(6) . . . . ? O1 C2 C3 C12 -178.4(3) . . . . ? C2 C3 C4 C5 2.7(6) . . . . ? C12 C3 C4 C5 179.5(4) . . . . ? C2 C3 C4 C15 -178.3(4) . . . . ? C12 C3 C4 C15 -1.5(7) . . . . ? C3 C4 C5 C10 -0.2(6) . . . . ? C15 C4 C5 C10 -179.2(4) . . . . ? C3 C4 C5 C6 179.1(4) . . . . ? C15 C4 C5 C6 0.1(6) . . . . ? C10 C5 C6 C7 0.2(6) . . . . ? C4 C5 C6 C7 -179.1(4) . . . . ? C5 C6 C7 C8 -0.6(7) . . . . ? C6 C7 C8 N19 179.8(4) . . . . ? C6 C7 C8 C9 0.4(7) . . . . ? N19 C8 C9 C10 -179.3(4) . . . . ? C7 C8 C9 C10 0.1(6) . . . . ? C8 C9 C10 O1 -176.9(4) . . . . ? C8 C9 C10 C5 -0.5(7) . . . . ? C2 O1 C10 C9 -177.7(4) . . . . ? C2 O1 C10 C5 5.8(6) . . . . ? C6 C5 C10 C9 0.4(6) . . . . ? C4 C5 C10 C9 179.7(4) . . . . ? C6 C5 C10 O1 176.6(3) . . . . ? C4 C5 C10 O1 -4.1(6) . . . . ? C4 C3 C12 N13 31.5(7) . . . . ? C2 C3 C12 N13 -151.4(4) . . . . ? C3 C12 N13 O14 179.9(3) . . . . ? C3 C4 C15 C16 -95.5(5) . . . . ? C5 C4 C15 C16 83.5(5) . . . . ? C4 C15 C16 C17 173.9(4) . . . . ? C15 C16 C17 C18 -69.1(5) . . . . ? C9 C8 N19 C20 9.8(6) . . . . ? C7 C8 N19 C20 -169.6(4) . . . . ? C9 C8 N19 C22 -164.0(4) . . . . ? C7 C8 N19 C22 16.6(6) . . . . ? C8 N19 C20 C21 -85.6(5) . . . . ? C22 N19 C20 C21 88.5(5) . . . . ? C8 N19 C22 C23 -96.0(5) . . . . ? C20 N19 C22 C23 89.8(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 O14 H14 O11 0.96(6) 1.73(6) 2.673(4) 170(6) 4_575 O14' H14' O11' 0.95(5) 1.73(5) 2.674(4) 171(4) 4_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.558 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.059