# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_cu_nwn79_0m _database_code_depnum_ccdc_archive 'CCDC 900340' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H33 Cl2 N O6' _chemical_formula_weight 526.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6090(3) _cell_length_b 15.8952(4) _cell_length_c 16.3523(4) _cell_angle_alpha 93.8650(10) _cell_angle_beta 100.2260(10) _cell_angle_gamma 90.9150(10) _cell_volume 2706.45(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 118 _cell_measurement_theta_min 15.71 _cell_measurement_theta_max 75.15 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 2.488 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7026 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'ImuS-focus sealed tube' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'APEX II DUO' _diffrn_measurement_method 'omega/phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30958 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 66.59 _reflns_number_total 9133 _reflns_number_gt 8138 _reflns_threshold_expression >2sigma(I) _computing_data_collection COSMO _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. The Alert _diffrn_measured_fraction_theta_full Low is cause by the geometrical boarders of the machine. The three circuits didn't allow the 100 % measurement, with the choosen orientation of the crystal. Calc. and Reported SumFormula differ because one the CH2Cl2 is highly disordered and was refined with the SUMP card which gives an occupation near 100% but not exactly. The crystals had not the best quality; the were very small not clear in their appearence. ; _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^)+(0.0693P)^2^+2.9890P] 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 9133 _refine_ls_number_parameters 658 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1364 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _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 C2 C 1.0851(2) 0.18676(13) 0.96372(13) 0.0151(4) Uani 1 1 d . . . C3 C 1.1834(2) 0.17406(13) 1.04476(13) 0.0154(4) Uani 1 1 d . . . C4 C 1.2551(2) 0.25758(14) 1.06503(13) 0.0183(4) Uani 1 1 d . . . H4 H 1.3157 0.2724 1.0317 0.022 Uiso 1 1 calc R . . C5 C 1.2373(2) 0.31155(14) 1.12771(14) 0.0213(5) Uani 1 1 d . . . H5 H 1.2827 0.3643 1.1361 0.026 Uiso 1 1 calc R . . C6 C 1.1495(2) 0.29167(15) 1.18403(14) 0.0237(5) Uani 1 1 d . . . C7 C 1.0972(2) 0.20459(15) 1.17499(14) 0.0216(5) Uani 1 1 d . . . H7 H 1.0497 0.1865 1.2150 0.026 Uiso 1 1 calc R . . C8 C 1.1142(2) 0.15052(14) 1.11267(13) 0.0179(4) Uani 1 1 d . . . H8 H 1.0812 0.0944 1.1110 0.021 Uiso 1 1 calc R . . C9 C 1.2680(2) 0.10273(13) 1.01194(13) 0.0160(4) Uani 1 1 d . . . C10 C 1.4021(2) 0.10389(14) 1.06010(13) 0.0195(5) Uani 1 1 d . . . H10 H 1.4517 0.1549 1.0653 0.023 Uiso 1 1 calc R . . C11 C 1.4552(2) 0.03717(16) 1.09604(14) 0.0236(5) Uani 1 1 d . . . H11 H 1.5407 0.0425 1.1259 0.028 Uiso 1 1 calc R . . C12 C 1.3863(2) -0.04427(15) 1.09101(14) 0.0244(5) Uani 1 1 d . . . C13 C 1.2531(2) -0.04773(14) 1.04616(14) 0.0214(5) Uani 1 1 d . . . H13 H 1.2036 -0.0986 1.0431 0.026 Uiso 1 1 calc R . . C14 C 1.2004(2) 0.01878(13) 1.00982(13) 0.0181(4) Uani 1 1 d . . . H14 H 1.1146 0.0128 0.9807 0.022 Uiso 1 1 calc R . . C15 C 1.26530(19) 0.12482(13) 0.92014(13) 0.0162(4) Uani 1 1 d . . . H15A H 1.3359 0.1650 0.9163 0.019 Uiso 1 1 calc R . . H15B H 1.2717 0.0735 0.8835 0.019 Uiso 1 1 calc R . . C16 C 1.0710(2) 0.16936(13) 0.81423(12) 0.0158(4) Uani 1 1 d . . . H16 H 1.0178 0.2207 0.8139 0.019 Uiso 1 1 calc R . . C17 C 1.1592(2) 0.17706(13) 0.75030(13) 0.0182(4) Uani 1 1 d . . . H17A H 1.1122 0.1999 0.6991 0.022 Uiso 1 1 calc R . . H17B H 1.2334 0.2153 0.7734 0.022 Uiso 1 1 calc R . . C19 C 1.2676(2) 0.08229(15) 0.66226(13) 0.0201(5) Uani 1 1 d . . . C20 C 1.3895(2) 0.13723(16) 0.67684(14) 0.0250(5) Uani 1 1 d . . . H20A H 1.3669 0.1966 0.6739 0.038 Uiso 1 1 calc R . . H20B H 1.4405 0.1216 0.6340 0.038 Uiso 1 1 calc R . . H20C H 1.4394 0.1288 0.7320 0.038 Uiso 1 1 calc R . . C21 C 1.2990(3) -0.01023(16) 0.66196(15) 0.0295(5) Uani 1 1 d . . . H21A H 1.3541 -0.0211 0.7147 0.044 Uiso 1 1 calc R . . H21B H 1.3437 -0.0252 0.6157 0.044 Uiso 1 1 calc R . . H21C H 1.2196 -0.0443 0.6552 0.044 Uiso 1 1 calc R . . C22 C 1.1800(2) 0.10098(17) 0.58115(14) 0.0265(5) Uani 1 1 d . . . H22A H 1.0987 0.0692 0.5760 0.040 Uiso 1 1 calc R . . H22B H 1.2215 0.0842 0.5338 0.040 Uiso 1 1 calc R . . H22C H 1.1636 0.1615 0.5816 0.040 Uiso 1 1 calc R . . C23 C 0.9812(2) 0.09213(14) 0.78866(13) 0.0171(4) Uani 1 1 d . . . C25 C 0.8159(2) 0.03492(14) 0.67260(14) 0.0213(5) Uani 1 1 d . . . C26 C 0.8890(2) -0.04262(15) 0.65300(14) 0.0242(5) Uani 1 1 d . . . H26A H 0.9492 -0.0286 0.6167 0.036 Uiso 1 1 calc R . . H26B H 0.8286 -0.0872 0.6248 0.036 Uiso 1 1 calc R . . H26C H 0.9363 -0.0624 0.7049 0.036 Uiso 1 1 calc R . . C27 C 0.7546(2) 0.07452(16) 0.59388(15) 0.0282(5) Uani 1 1 d . . . H27A H 0.7110 0.1257 0.6088 0.042 Uiso 1 1 calc R . . H27B H 0.6923 0.0344 0.5600 0.042 Uiso 1 1 calc R . . H27C H 0.8209 0.0891 0.5621 0.042 Uiso 1 1 calc R . . C28 C 0.7160(2) 0.01726(18) 0.72613(15) 0.0296(6) Uani 1 1 d . . . H28A H 0.7555 -0.0125 0.7743 0.044 Uiso 1 1 calc R . . H28B H 0.6458 -0.0178 0.6931 0.044 Uiso 1 1 calc R . . H28C H 0.6824 0.0707 0.7453 0.044 Uiso 1 1 calc R . . C102 C 0.5805(2) 0.31562(13) 0.95571(13) 0.0166(4) Uani 1 1 d . . . C103 C 0.6782(2) 0.33590(13) 1.03804(13) 0.0161(4) Uani 1 1 d . . . C104 C 0.6109(2) 0.36682(14) 1.10708(13) 0.0183(4) Uani 1 1 d . . . H104 H 0.5715 0.4200 1.1038 0.022 Uiso 1 1 calc R . . C105 C 0.6040(2) 0.32299(15) 1.17254(14) 0.0236(5) Uani 1 1 d . . . H105 H 0.5581 0.3452 1.2136 0.028 Uiso 1 1 calc R . . C106 C 0.6649(3) 0.24161(17) 1.18363(15) 0.0314(6) Uani 1 1 d . . . C107 C 0.7395(2) 0.21190(15) 1.12027(14) 0.0226(5) Uani 1 1 d . . . H107 H 0.7834 0.1604 1.1262 0.027 Uiso 1 1 calc R . . C108 C 0.7468(2) 0.25573(13) 1.05480(13) 0.0179(4) Uani 1 1 d . . . H108 H 0.7984 0.2349 1.0165 0.021 Uiso 1 1 calc R . . C109 C 0.7671(2) 0.40480(13) 1.00843(13) 0.0161(4) Uani 1 1 d . . . C110 C 0.8997(2) 0.40878(14) 1.05946(13) 0.0179(4) Uani 1 1 d . . . H110 H 0.9479 0.3589 1.0617 0.021 Uiso 1 1 calc R . . C111 C 0.9531(2) 0.47874(15) 1.10172(13) 0.0210(5) Uani 1 1 d . . . H111 H 1.0367 0.4766 1.1339 0.025 Uiso 1 1 calc R . . C112 C 0.8869(2) 0.55908(14) 1.10007(14) 0.0220(5) Uani 1 1 d . . . C113 C 0.7563(2) 0.55780(14) 1.05150(14) 0.0207(5) Uani 1 1 d . . . H113 H 0.7089 0.6080 1.0504 0.025 Uiso 1 1 calc R . . C114 C 0.7027(2) 0.48790(14) 1.00891(13) 0.0189(4) Uani 1 1 d . . . H114 H 0.6190 0.4910 0.9771 0.023 Uiso 1 1 calc R . . C115 C 0.7661(2) 0.37212(14) 0.91629(13) 0.0171(4) Uani 1 1 d . . . H11A H 0.7761 0.4193 0.8812 0.020 Uiso 1 1 calc R . . H11B H 0.8350 0.3316 0.9123 0.020 Uiso 1 1 calc R . . C116 C 0.5733(2) 0.31329(14) 0.80670(13) 0.0178(4) Uani 1 1 d . . . H116 H 0.5157 0.2626 0.8055 0.021 Uiso 1 1 calc R . . C117 C 0.6628(2) 0.29389(14) 0.74469(13) 0.0190(4) Uani 1 1 d . . . H11C H 0.7340 0.2590 0.7695 0.023 Uiso 1 1 calc R . . H11D H 0.6155 0.2629 0.6936 0.023 Uiso 1 1 calc R . . C119 C 0.7727(2) 0.37302(14) 0.65287(13) 0.0201(5) Uani 1 1 d . . . C120 C 0.8906(2) 0.31931(16) 0.66457(14) 0.0246(5) Uani 1 1 d . . . H12A H 0.9461 0.3372 0.7176 0.037 Uiso 1 1 calc R . . H12B H 0.9373 0.3261 0.6187 0.037 Uiso 1 1 calc R . . H12C H 0.8644 0.2599 0.6649 0.037 Uiso 1 1 calc R . . C121 C 0.8095(3) 0.46559(15) 0.65107(16) 0.0294(5) Uani 1 1 d . . . H12D H 0.7322 0.4993 0.6460 0.044 Uiso 1 1 calc R . . H12E H 0.8518 0.4731 0.6033 0.044 Uiso 1 1 calc R . . H12F H 0.8681 0.4841 0.7027 0.044 Uiso 1 1 calc R . . C122 C 0.6789(2) 0.34304(16) 0.57380(14) 0.0263(5) Uani 1 1 d . . . H12G H 0.6587 0.2828 0.5750 0.040 Uiso 1 1 calc R . . H12H H 0.7177 0.3523 0.5249 0.040 Uiso 1 1 calc R . . H12I H 0.6000 0.3748 0.5708 0.040 Uiso 1 1 calc R . . C123 C 0.4893(2) 0.38699(15) 0.77924(13) 0.0197(5) Uani 1 1 d . . . C125 C 0.3265(2) 0.42489(16) 0.66154(15) 0.0261(5) Uani 1 1 d . . . C126 C 0.2263(2) 0.44834(18) 0.71452(17) 0.0330(6) Uani 1 1 d . . . H12J H 0.1920 0.3971 0.7337 0.049 Uiso 1 1 calc R . . H12K H 0.1566 0.4775 0.6812 0.049 Uiso 1 1 calc R . . H12L H 0.2658 0.4856 0.7628 0.049 Uiso 1 1 calc R . . C127 C 0.2668(3) 0.37259(19) 0.58263(17) 0.0385(6) Uani 1 1 d . . . H12M H 0.3346 0.3515 0.5537 0.058 Uiso 1 1 calc R . . H12N H 0.2097 0.4077 0.5462 0.058 Uiso 1 1 calc R . . H12O H 0.2177 0.3248 0.5971 0.058 Uiso 1 1 calc R . . C128 C 0.4005(3) 0.50085(17) 0.64158(16) 0.0314(6) Uani 1 1 d . . . H12P H 0.4446 0.5306 0.6935 0.047 Uiso 1 1 calc R . . H12Q H 0.3411 0.5389 0.6106 0.047 Uiso 1 1 calc R . . H12R H 0.4637 0.4822 0.6077 0.047 Uiso 1 1 calc R . . N1 N 1.14094(16) 0.16307(11) 0.89829(10) 0.0147(4) Uani 1 1 d . . . N101 N 0.63956(16) 0.33085(11) 0.89191(11) 0.0162(4) Uani 1 1 d . . . O2 O 0.97859(14) 0.21476(10) 0.96095(9) 0.0201(3) Uani 1 1 d . . . O6 O 1.1219(2) 0.34428(12) 1.23566(11) 0.0366(4) Uani 1 1 d . . . O12 O 1.43653(18) -0.10653(12) 1.12206(11) 0.0344(4) Uani 1 1 d . . . O18 O 1.20107(14) 0.09497(9) 0.73225(9) 0.0185(3) Uani 1 1 d . . . O23 O 0.97910(15) 0.03238(10) 0.83008(9) 0.0224(3) Uani 1 1 d . . . O24 O 0.90708(15) 0.10272(10) 0.71531(9) 0.0199(3) Uani 1 1 d . . . O102 O 0.47100(14) 0.28826(10) 0.95067(9) 0.0205(3) Uani 1 1 d . . . O106 O 0.6565(3) 0.20066(17) 1.24308(15) 0.0706(9) Uani 1 1 d . . . O112 O 0.93793(17) 0.62414(11) 1.13655(11) 0.0310(4) Uani 1 1 d . . . O118 O 0.71058(15) 0.37257(9) 0.72562(9) 0.0201(3) Uani 1 1 d . . . O123 O 0.48959(16) 0.45330(10) 0.81957(10) 0.0251(4) Uani 1 1 d . . . O124 O 0.41670(15) 0.36519(10) 0.70520(9) 0.0234(3) Uani 1 1 d . . . C100 C 1.4923(6) 0.2098(3) 0.3774(3) 0.0871(14) Uani 1 1 d U . . H10A H 1.5836 0.2285 0.3913 0.105 Uiso 1 1 calc R . . H10B H 1.4814 0.1721 0.3258 0.105 Uiso 1 1 calc R . . C200 C 0.9358(6) 0.3161(3) 1.3723(3) 0.0891(14) Uani 1 1 d DU . . H20D H 0.8530 0.3163 1.3333 0.107 Uiso 1 1 calc R . . H20E H 1.0044 0.3239 1.3394 0.107 Uiso 1 1 calc R . . Cl11 Cl 1.45654(7) 0.15277(5) 0.45722(5) 0.0476(2) Uani 1 1 d . . . Cl12 Cl 1.40042(14) 0.29660(9) 0.35813(7) 0.0921(4) Uani 1 1 d . . . Cl21 Cl 0.94214(7) 0.40295(4) 1.44440(4) 0.03874(17) Uani 1 1 d . . . Cl22 Cl 0.951(3) 0.2218(8) 1.4098(13) 0.120(3) Uani 0.30(3) 1 d PD . . Cl2A Cl 0.982(2) 0.2264(5) 1.4300(13) 0.120(3) Uani 0.43(3) 1 d P . . Cl2B Cl 0.8987(8) 0.2323(4) 1.3671(6) 0.083(3) Uani 0.230(7) 1 d P . . 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 C2 0.0174(10) 0.0110(10) 0.0179(10) 0.0005(8) 0.0060(8) -0.0013(8) C3 0.0167(10) 0.0130(10) 0.0175(10) 0.0007(8) 0.0059(8) 0.0003(9) C4 0.0185(10) 0.0160(11) 0.0207(10) 0.0021(8) 0.0040(8) -0.0014(9) C5 0.0242(11) 0.0154(11) 0.0231(11) -0.0007(8) 0.0018(9) -0.0016(9) C6 0.0286(12) 0.0228(12) 0.0189(11) -0.0029(9) 0.0030(9) 0.0048(10) C7 0.0240(11) 0.0235(12) 0.0198(11) 0.0046(9) 0.0091(9) 0.0045(10) C8 0.0183(10) 0.0158(10) 0.0209(11) 0.0039(8) 0.0066(8) 0.0011(9) C9 0.0162(10) 0.0153(10) 0.0171(10) 0.0001(8) 0.0046(8) 0.0014(8) C10 0.0178(10) 0.0230(12) 0.0183(10) -0.0012(9) 0.0055(8) 0.0019(9) C11 0.0199(11) 0.0333(13) 0.0182(11) 0.0012(9) 0.0044(9) 0.0081(10) C12 0.0332(13) 0.0248(12) 0.0188(11) 0.0038(9) 0.0125(9) 0.0140(11) C13 0.0281(12) 0.0154(11) 0.0234(11) 0.0000(9) 0.0117(9) 0.0037(9) C14 0.0195(10) 0.0172(11) 0.0184(10) -0.0018(8) 0.0071(8) -0.0001(9) C15 0.0136(10) 0.0170(10) 0.0185(10) 0.0007(8) 0.0045(8) 0.0033(8) C16 0.0163(10) 0.0156(10) 0.0156(10) 0.0011(8) 0.0033(8) 0.0012(8) C17 0.0216(11) 0.0166(11) 0.0178(10) 0.0025(8) 0.0066(8) -0.0001(9) C19 0.0205(11) 0.0262(12) 0.0148(10) -0.0016(8) 0.0073(8) 0.0018(10) C20 0.0199(11) 0.0347(14) 0.0218(11) 0.0003(10) 0.0077(9) 0.0006(10) C21 0.0377(14) 0.0272(13) 0.0259(12) -0.0016(10) 0.0125(10) 0.0071(11) C22 0.0271(12) 0.0354(14) 0.0172(11) 0.0006(9) 0.0053(9) -0.0017(11) C23 0.0160(10) 0.0200(11) 0.0161(10) 0.0000(8) 0.0050(8) 0.0012(9) C25 0.0206(11) 0.0222(12) 0.0196(11) -0.0021(9) 0.0010(9) -0.0040(9) C26 0.0280(12) 0.0224(12) 0.0217(11) -0.0017(9) 0.0041(9) -0.0012(10) C27 0.0305(13) 0.0279(13) 0.0225(12) -0.0013(9) -0.0041(10) -0.0003(11) C28 0.0209(11) 0.0409(15) 0.0261(12) -0.0045(10) 0.0052(9) -0.0058(11) C102 0.0184(10) 0.0123(10) 0.0202(10) 0.0007(8) 0.0065(8) 0.0012(9) C103 0.0149(10) 0.0155(10) 0.0192(10) 0.0011(8) 0.0067(8) -0.0012(9) C104 0.0161(10) 0.0174(11) 0.0218(11) -0.0026(8) 0.0057(8) 0.0010(9) C105 0.0245(11) 0.0276(12) 0.0202(11) -0.0009(9) 0.0091(9) 0.0019(10) C106 0.0390(14) 0.0345(14) 0.0239(12) 0.0086(10) 0.0111(11) 0.0073(12) C107 0.0221(11) 0.0189(11) 0.0270(12) 0.0037(9) 0.0042(9) 0.0027(9) C108 0.0155(10) 0.0154(10) 0.0234(11) -0.0016(8) 0.0062(8) -0.0001(9) C109 0.0158(10) 0.0139(10) 0.0194(10) 0.0015(8) 0.0053(8) -0.0014(9) C110 0.0154(10) 0.0186(11) 0.0207(10) 0.0041(8) 0.0052(8) 0.0000(9) C111 0.0178(10) 0.0259(12) 0.0194(10) 0.0031(9) 0.0031(8) -0.0039(9) C112 0.0281(12) 0.0200(11) 0.0201(11) 0.0016(9) 0.0105(9) -0.0072(10) C113 0.0263(11) 0.0138(10) 0.0239(11) 0.0037(8) 0.0091(9) 0.0005(9) C114 0.0169(10) 0.0190(11) 0.0219(11) 0.0048(8) 0.0048(8) 0.0017(9) C115 0.0141(10) 0.0191(11) 0.0183(10) 0.0004(8) 0.0044(8) -0.0030(9) C116 0.0172(10) 0.0191(11) 0.0171(10) -0.0005(8) 0.0039(8) -0.0029(9) C117 0.0209(10) 0.0159(11) 0.0211(11) 0.0000(8) 0.0070(9) -0.0004(9) C119 0.0218(11) 0.0224(12) 0.0177(10) 0.0000(8) 0.0083(9) -0.0015(9) C120 0.0207(11) 0.0310(13) 0.0238(11) 0.0029(9) 0.0080(9) 0.0004(10) C121 0.0391(14) 0.0226(12) 0.0297(13) 0.0016(10) 0.0159(11) -0.0040(11) C122 0.0253(12) 0.0334(13) 0.0204(11) 0.0020(9) 0.0043(9) 0.0002(10) C123 0.0158(10) 0.0244(12) 0.0200(11) 0.0013(9) 0.0066(8) -0.0001(9) C125 0.0230(11) 0.0295(13) 0.0256(12) 0.0062(10) 0.0016(9) 0.0056(10) C126 0.0233(12) 0.0424(16) 0.0350(14) 0.0097(11) 0.0070(10) 0.0064(11) C127 0.0370(15) 0.0418(16) 0.0318(14) 0.0044(12) -0.0080(11) 0.0056(13) C128 0.0317(13) 0.0344(14) 0.0310(13) 0.0096(11) 0.0101(10) 0.0080(12) N1 0.0130(8) 0.0155(9) 0.0161(8) 0.0007(7) 0.0041(7) 0.0017(7) N101 0.0136(8) 0.0175(9) 0.0180(9) 0.0002(7) 0.0050(7) -0.0024(7) O2 0.0158(7) 0.0223(8) 0.0243(8) 0.0043(6) 0.0081(6) 0.0060(6) O6 0.0514(12) 0.0298(10) 0.0297(9) -0.0097(8) 0.0147(8) 0.0047(9) O12 0.0437(10) 0.0314(10) 0.0328(9) 0.0124(8) 0.0140(8) 0.0213(9) O18 0.0236(8) 0.0176(8) 0.0166(7) 0.0015(6) 0.0096(6) 0.0026(6) O23 0.0241(8) 0.0227(8) 0.0203(8) 0.0049(6) 0.0029(6) -0.0053(7) O24 0.0223(8) 0.0187(8) 0.0173(7) 0.0006(6) -0.0001(6) -0.0014(6) O102 0.0145(7) 0.0224(8) 0.0257(8) -0.0009(6) 0.0076(6) -0.0041(6) O106 0.111(2) 0.0702(16) 0.0524(14) 0.0448(13) 0.0546(15) 0.0513(16) O112 0.0361(10) 0.0227(9) 0.0339(9) -0.0062(7) 0.0092(8) -0.0124(8) O118 0.0252(8) 0.0169(8) 0.0203(8) -0.0006(6) 0.0108(6) -0.0025(6) O123 0.0256(8) 0.0236(9) 0.0256(8) -0.0028(7) 0.0043(7) 0.0061(7) O124 0.0228(8) 0.0251(9) 0.0208(8) 0.0013(6) 0.0004(6) 0.0021(7) C100 0.118(3) 0.083(3) 0.078(3) 0.027(2) 0.057(2) 0.007(3) C200 0.125(3) 0.083(3) 0.067(2) -0.014(2) 0.044(2) -0.001(3) Cl11 0.0480(4) 0.0544(5) 0.0409(4) 0.0065(3) 0.0093(3) -0.0123(4) Cl12 0.1159(9) 0.1066(9) 0.0688(7) 0.0450(6) 0.0390(6) 0.0468(8) Cl21 0.0409(4) 0.0383(4) 0.0391(4) 0.0057(3) 0.0116(3) 0.0016(3) Cl22 0.203(9) 0.0425(12) 0.087(6) -0.021(2) -0.045(5) 0.048(2) Cl2A 0.203(9) 0.0425(12) 0.087(6) -0.021(2) -0.045(5) 0.048(2) Cl2B 0.100(5) 0.055(3) 0.098(6) -0.040(3) 0.050(4) -0.035(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 C2 O2 1.215(3) . ? C2 N1 1.347(3) . ? C2 C3 1.561(3) . ? C3 C8 1.499(3) . ? C3 C4 1.507(3) . ? C3 C9 1.582(3) . ? C4 C5 1.333(3) . ? C4 H4 0.9500 . ? C5 C6 1.466(3) . ? C5 H5 0.9500 . ? C6 O6 1.224(3) . ? C6 C7 1.471(3) . ? C7 C8 1.328(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.497(3) . ? C9 C14 1.500(3) . ? C9 C15 1.560(3) . ? C10 C11 1.332(3) . ? C10 H10 0.9500 . ? C11 C12 1.467(4) . ? C11 H11 0.9500 . ? C12 O12 1.229(3) . ? C12 C13 1.470(3) . ? C13 C14 1.330(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.458(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.452(3) . ? C16 C23 1.530(3) . ? C16 C17 1.531(3) . ? C16 H16 1.0000 . ? C17 O18 1.414(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C19 O18 1.452(2) . ? C19 C21 1.513(3) . ? C19 C20 1.522(3) . ? C19 C22 1.529(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O23 1.205(3) . ? C23 O24 1.335(3) . ? C25 O24 1.487(3) . ? C25 C26 1.513(3) . ? C25 C27 1.517(3) . ? C25 C28 1.524(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C102 O102 1.221(3) . ? C102 N101 1.342(3) . ? C102 C103 1.557(3) . ? C103 C108 1.495(3) . ? C103 C104 1.500(3) . ? C103 C109 1.589(3) . ? C104 C105 1.328(3) . ? C104 H104 0.9500 . ? C105 C106 1.463(4) . ? C105 H105 0.9500 . ? C106 O106 1.221(3) . ? C106 C107 1.470(3) . ? C107 C108 1.329(3) . ? C107 H107 0.9500 . ? C108 H108 0.9500 . ? C109 C114 1.497(3) . ? C109 C110 1.501(3) . ? C109 C115 1.558(3) . ? C110 C111 1.332(3) . ? C110 H110 0.9500 . ? C111 C112 1.467(3) . ? C111 H111 0.9500 . ? C112 O112 1.226(3) . ? C112 C113 1.469(3) . ? C113 C114 1.333(3) . ? C113 H113 0.9500 . ? C114 H114 0.9500 . ? C115 N101 1.462(3) . ? C115 H11A 0.9900 . ? C115 H11B 0.9900 . ? C116 N101 1.452(3) . ? C116 C123 1.526(3) . ? C116 C117 1.528(3) . ? C116 H116 1.0000 . ? C117 O118 1.417(3) . ? C117 H11C 0.9900 . ? C117 H11D 0.9900 . ? C119 O118 1.459(2) . ? C119 C120 1.517(3) . ? C119 C121 1.520(3) . ? C119 C122 1.528(3) . ? C120 H12A 0.9800 . ? C120 H12B 0.9800 . ? C120 H12C 0.9800 . ? C121 H12D 0.9800 . ? C121 H12E 0.9800 . ? C121 H12F 0.9800 . ? C122 H12G 0.9800 . ? C122 H12H 0.9800 . ? C122 H12I 0.9800 . ? C123 O123 1.205(3) . ? C123 O124 1.335(3) . ? C125 O124 1.484(3) . ? C125 C128 1.515(4) . ? C125 C127 1.518(4) . ? C125 C126 1.522(3) . ? C126 H12J 0.9800 . ? C126 H12K 0.9800 . ? C126 H12L 0.9800 . ? C127 H12M 0.9800 . ? C127 H12N 0.9800 . ? C127 H12O 0.9800 . ? C128 H12P 0.9800 . ? C128 H12Q 0.9800 . ? C128 H12R 0.9800 . ? C100 Cl12 1.716(5) . ? C100 Cl11 1.730(4) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? C200 Cl22 1.657(9) . ? C200 Cl21 1.746(4) . ? C200 H20D 0.9900 . ? C200 H20E 0.9900 . ? Cl22 Cl2B 0.839(15) . ? Cl2A Cl2B 1.24(2) . ? 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 C2 N1 126.7(2) . . ? O2 C2 C3 125.64(18) . . ? N1 C2 C3 107.66(17) . . ? C8 C3 C4 112.51(17) . . ? C8 C3 C2 110.03(17) . . ? C4 C3 C2 104.54(16) . . ? C8 C3 C9 115.32(17) . . ? C4 C3 C9 112.50(17) . . ? C2 C3 C9 100.69(16) . . ? C5 C4 C3 122.9(2) . . ? C5 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? O6 C6 C5 122.0(2) . . ? O6 C6 C7 122.0(2) . . ? C5 C6 C7 115.97(19) . . ? C8 C7 C6 122.0(2) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C7 C8 C3 122.9(2) . . ? C7 C8 H8 118.5 . . ? C3 C8 H8 118.5 . . ? C10 C9 C14 112.54(19) . . ? C10 C9 C15 111.57(17) . . ? C14 C9 C15 107.87(17) . . ? C10 C9 C3 113.11(17) . . ? C14 C9 C3 109.19(17) . . ? C15 C9 C3 101.95(16) . . ? C11 C10 C9 123.4(2) . . ? C11 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C10 C11 C12 122.2(2) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? O12 C12 C11 122.2(2) . . ? O12 C12 C13 121.5(2) . . ? C11 C12 C13 116.3(2) . . ? C14 C13 C12 121.4(2) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C9 124.1(2) . . ? C13 C14 H14 117.9 . . ? C9 C14 H14 117.9 . . ? N1 C15 C9 103.02(16) . . ? N1 C15 H15A 111.2 . . ? C9 C15 H15A 111.2 . . ? N1 C15 H15B 111.2 . . ? C9 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? N1 C16 C23 109.66(17) . . ? N1 C16 C17 112.87(17) . . ? C23 C16 C17 109.32(17) . . ? N1 C16 H16 108.3 . . ? C23 C16 H16 108.3 . . ? C17 C16 H16 108.3 . . ? O18 C17 C16 106.77(16) . . ? O18 C17 H17A 110.4 . . ? C16 C17 H17A 110.4 . . ? O18 C17 H17B 110.4 . . ? C16 C17 H17B 110.4 . . ? H17A C17 H17B 108.6 . . ? O18 C19 C21 103.41(17) . . ? O18 C19 C20 110.15(17) . . ? C21 C19 C20 110.8(2) . . ? O18 C19 C22 110.48(18) . . ? C21 C19 C22 110.69(19) . . ? C20 C19 C22 111.03(19) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O23 C23 O24 126.7(2) . . ? O23 C23 C16 123.98(19) . . ? O24 C23 C16 109.31(17) . . ? O24 C25 C26 109.66(18) . . ? O24 C25 C27 102.36(17) . . ? C26 C25 C27 111.50(19) . . ? O24 C25 C28 109.69(18) . . ? C26 C25 C28 112.6(2) . . ? C27 C25 C28 110.5(2) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O102 C102 N101 126.4(2) . . ? O102 C102 C103 125.62(18) . . ? N101 C102 C103 107.91(17) . . ? C108 C103 C104 113.11(18) . . ? C108 C103 C102 105.31(17) . . ? C104 C103 C102 110.77(17) . . ? C108 C103 C109 111.78(17) . . ? C104 C103 C109 114.67(18) . . ? C102 C103 C109 100.01(16) . . ? C105 C104 C103 122.8(2) . . ? C105 C104 H104 118.6 . . ? C103 C104 H104 118.6 . . ? C104 C105 C106 122.2(2) . . ? C104 C105 H105 118.9 . . ? C106 C105 H105 118.9 . . ? O106 C106 C105 122.1(2) . . ? O106 C106 C107 121.2(3) . . ? C105 C106 C107 116.6(2) . . ? C108 C107 C106 121.2(2) . . ? C108 C107 H107 119.4 . . ? C106 C107 H107 119.4 . . ? C107 C108 C103 123.7(2) . . ? C107 C108 H108 118.1 . . ? C103 C108 H108 118.1 . . ? C114 C109 C110 112.92(18) . . ? C114 C109 C115 108.61(17) . . ? C110 C109 C115 112.11(17) . . ? C114 C109 C103 108.97(17) . . ? C110 C109 C103 111.86(17) . . ? C115 C109 C103 101.75(16) . . ? C111 C110 C109 123.3(2) . . ? C111 C110 H110 118.3 . . ? C109 C110 H110 118.3 . . ? C110 C111 C112 122.0(2) . . ? C110 C111 H111 119.0 . . ? C112 C111 H111 119.0 . . ? O112 C112 C111 122.0(2) . . ? O112 C112 C113 121.6(2) . . ? C111 C112 C113 116.44(19) . . ? C114 C113 C112 121.6(2) . . ? C114 C113 H113 119.2 . . ? C112 C113 H113 119.2 . . ? C113 C114 C109 123.6(2) . . ? C113 C114 H114 118.2 . . ? C109 C114 H114 118.2 . . ? N101 C115 C109 102.79(16) . . ? N101 C115 H11A 111.2 . . ? C109 C115 H11A 111.2 . . ? N101 C115 H11B 111.2 . . ? C109 C115 H11B 111.2 . . ? H11A C115 H11B 109.1 . . ? N101 C116 C123 110.05(17) . . ? N101 C116 C117 113.73(18) . . ? C123 C116 C117 109.74(17) . . ? N101 C116 H116 107.7 . . ? C123 C116 H116 107.7 . . ? C117 C116 H116 107.7 . . ? O118 C117 C116 106.61(17) . . ? O118 C117 H11C 110.4 . . ? C116 C117 H11C 110.4 . . ? O118 C117 H11D 110.4 . . ? C116 C117 H11D 110.4 . . ? H11C C117 H11D 108.6 . . ? O118 C119 C120 110.42(18) . . ? O118 C119 C121 102.80(17) . . ? C120 C119 C121 111.0(2) . . ? O118 C119 C122 110.70(17) . . ? C120 C119 C122 111.16(19) . . ? C121 C119 C122 110.5(2) . . ? C119 C120 H12A 109.5 . . ? C119 C120 H12B 109.5 . . ? H12A C120 H12B 109.5 . . ? C119 C120 H12C 109.5 . . ? H12A C120 H12C 109.5 . . ? H12B C120 H12C 109.5 . . ? C119 C121 H12D 109.5 . . ? C119 C121 H12E 109.5 . . ? H12D C121 H12E 109.5 . . ? C119 C121 H12F 109.5 . . ? H12D C121 H12F 109.5 . . ? H12E C121 H12F 109.5 . . ? C119 C122 H12G 109.5 . . ? C119 C122 H12H 109.5 . . ? H12G C122 H12H 109.5 . . ? C119 C122 H12I 109.5 . . ? H12G C122 H12I 109.5 . . ? H12H C122 H12I 109.5 . . ? O123 C123 O124 126.7(2) . . ? O123 C123 C116 124.3(2) . . ? O124 C123 C116 109.06(18) . . ? O124 C125 C128 109.69(19) . . ? O124 C125 C127 102.2(2) . . ? C128 C125 C127 111.1(2) . . ? O124 C125 C126 109.36(19) . . ? C128 C125 C126 112.9(2) . . ? C127 C125 C126 111.1(2) . . ? C125 C126 H12J 109.5 . . ? C125 C126 H12K 109.5 . . ? H12J C126 H12K 109.5 . . ? C125 C126 H12L 109.5 . . ? H12J C126 H12L 109.5 . . ? H12K C126 H12L 109.5 . . ? C125 C127 H12M 109.5 . . ? C125 C127 H12N 109.5 . . ? H12M C127 H12N 109.5 . . ? C125 C127 H12O 109.5 . . ? H12M C127 H12O 109.5 . . ? H12N C127 H12O 109.5 . . ? C125 C128 H12P 109.5 . . ? C125 C128 H12Q 109.5 . . ? H12P C128 H12Q 109.5 . . ? C125 C128 H12R 109.5 . . ? H12P C128 H12R 109.5 . . ? H12Q C128 H12R 109.5 . . ? C2 N1 C16 119.52(18) . . ? C2 N1 C15 114.68(17) . . ? C16 N1 C15 125.51(17) . . ? C102 N101 C116 120.19(17) . . ? C102 N101 C115 114.55(17) . . ? C116 N101 C115 125.03(17) . . ? C17 O18 C19 117.64(16) . . ? C23 O24 C25 121.04(17) . . ? C117 O118 C119 117.21(16) . . ? C123 O124 C125 121.52(18) . . ? Cl12 C100 Cl11 114.5(3) . . ? Cl12 C100 H10A 108.6 . . ? Cl11 C100 H10A 108.6 . . ? Cl12 C100 H10B 108.6 . . ? Cl11 C100 H10B 108.6 . . ? H10A C100 H10B 107.6 . . ? Cl22 C200 Cl21 117.0(8) . . ? Cl22 C200 H20D 108.0 . . ? Cl21 C200 H20D 108.0 . . ? Cl22 C200 H20E 108.0 . . ? Cl21 C200 H20E 108.0 . . ? H20D C200 H20E 107.3 . . ? Cl2B Cl22 C200 55.9(7) . . ? Cl22 Cl2B Cl2A 7.7(15) . . ? 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 O2 C2 C3 C8 33.8(3) . . . . ? N1 C2 C3 C8 -147.65(18) . . . . ? O2 C2 C3 C4 -87.3(2) . . . . ? N1 C2 C3 C4 91.32(19) . . . . ? O2 C2 C3 C9 155.9(2) . . . . ? N1 C2 C3 C9 -25.5(2) . . . . ? C8 C3 C4 C5 -12.9(3) . . . . ? C2 C3 C4 C5 106.5(2) . . . . ? C9 C3 C4 C5 -145.1(2) . . . . ? C3 C4 C5 C6 2.6(4) . . . . ? C4 C5 C6 O6 -171.7(2) . . . . ? C4 C5 C6 C7 8.6(3) . . . . ? O6 C6 C7 C8 171.5(2) . . . . ? C5 C6 C7 C8 -8.7(3) . . . . ? C6 C7 C8 C3 -2.4(4) . . . . ? C4 C3 C8 C7 12.7(3) . . . . ? C2 C3 C8 C7 -103.4(2) . . . . ? C9 C3 C8 C7 143.6(2) . . . . ? C8 C3 C9 C10 -88.4(2) . . . . ? C4 C3 C9 C10 42.4(2) . . . . ? C2 C3 C9 C10 153.21(17) . . . . ? C8 C3 C9 C14 37.7(2) . . . . ? C4 C3 C9 C14 168.58(17) . . . . ? C2 C3 C9 C14 -80.65(19) . . . . ? C8 C3 C9 C15 151.64(17) . . . . ? C4 C3 C9 C15 -77.5(2) . . . . ? C2 C3 C9 C15 33.29(18) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C15 C9 C10 C11 -120.6(2) . . . . ? C3 C9 C10 C11 125.1(2) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 O12 177.8(2) . . . . ? C10 C11 C12 C13 -1.9(3) . . . . ? O12 C12 C13 C14 -177.3(2) . . . . ? C11 C12 C13 C14 2.3(3) . . . . ? C12 C13 C14 C9 -1.3(3) . . . . ? C10 C9 C14 C13 -0.3(3) . . . . ? C15 C9 C14 C13 123.2(2) . . . . ? C3 C9 C14 C13 -126.8(2) . . . . ? C10 C9 C15 N1 -151.37(17) . . . . ? C14 C9 C15 N1 84.5(2) . . . . ? C3 C9 C15 N1 -30.37(19) . . . . ? N1 C16 C17 O18 78.9(2) . . . . ? C23 C16 C17 O18 -43.5(2) . . . . ? N1 C16 C23 O23 -6.2(3) . . . . ? C17 C16 C23 O23 118.0(2) . . . . ? N1 C16 C23 O24 173.12(16) . . . . ? C17 C16 C23 O24 -62.6(2) . . . . ? O102 C102 C103 C108 89.3(2) . . . . ? N101 C102 C103 C108 -88.6(2) . . . . ? O102 C102 C103 C104 -33.3(3) . . . . ? N101 C102 C103 C104 148.75(18) . . . . ? O102 C102 C103 C109 -154.6(2) . . . . ? N101 C102 C103 C109 27.4(2) . . . . ? C108 C103 C104 C105 -5.7(3) . . . . ? C102 C103 C104 C105 112.3(2) . . . . ? C109 C103 C104 C105 -135.5(2) . . . . ? C103 C104 C105 C106 1.7(4) . . . . ? C104 C105 C106 O106 -178.6(3) . . . . ? C104 C105 C106 C107 2.6(4) . . . . ? O106 C106 C107 C108 178.8(3) . . . . ? C105 C106 C107 C108 -2.4(4) . . . . ? C106 C107 C108 C103 -2.0(4) . . . . ? C104 C103 C108 C107 5.9(3) . . . . ? C102 C103 C108 C107 -115.2(2) . . . . ? C109 C103 C108 C107 137.1(2) . . . . ? C108 C103 C109 C114 -169.01(18) . . . . ? C104 C103 C109 C114 -38.6(2) . . . . ? C102 C103 C109 C114 79.93(19) . . . . ? C108 C103 C109 C110 -43.4(2) . . . . ? C104 C103 C109 C110 87.0(2) . . . . ? C102 C103 C109 C110 -154.50(17) . . . . ? C108 C103 C109 C115 76.4(2) . . . . ? C104 C103 C109 C115 -153.17(18) . . . . ? C102 C103 C109 C115 -34.66(19) . . . . ? C114 C109 C110 C111 1.0(3) . . . . ? C115 C109 C110 C111 124.1(2) . . . . ? C103 C109 C110 C111 -122.3(2) . . . . ? C109 C110 C111 C112 -1.5(3) . . . . ? C110 C111 C112 O112 -177.3(2) . . . . ? C110 C111 C112 C113 2.0(3) . . . . ? O112 C112 C113 C114 177.1(2) . . . . ? C111 C112 C113 C114 -2.2(3) . . . . ? C112 C113 C114 C109 2.0(3) . . . . ? C110 C109 C114 C113 -1.3(3) . . . . ? C115 C109 C114 C113 -126.3(2) . . . . ? C103 C109 C114 C113 123.7(2) . . . . ? C114 C109 C115 N101 -83.97(19) . . . . ? C110 C109 C115 N101 150.55(18) . . . . ? C103 C109 C115 N101 30.9(2) . . . . ? N101 C116 C117 O118 -80.6(2) . . . . ? C123 C116 C117 O118 43.1(2) . . . . ? N101 C116 C123 O123 7.4(3) . . . . ? C117 C116 C123 O123 -118.4(2) . . . . ? N101 C116 C123 O124 -171.91(16) . . . . ? C117 C116 C123 O124 62.2(2) . . . . ? O2 C2 N1 C16 -0.7(3) . . . . ? C3 C2 N1 C16 -179.23(16) . . . . ? O2 C2 N1 C15 -174.9(2) . . . . ? C3 C2 N1 C15 6.6(2) . . . . ? C23 C16 N1 C2 -82.3(2) . . . . ? C17 C16 N1 C2 155.59(18) . . . . ? C23 C16 N1 C15 91.2(2) . . . . ? C17 C16 N1 C15 -30.9(3) . . . . ? C9 C15 N1 C2 15.8(2) . . . . ? C9 C15 N1 C16 -158.00(18) . . . . ? O102 C102 N101 C116 -1.1(3) . . . . ? C103 C102 N101 C116 176.86(18) . . . . ? O102 C102 N101 C115 173.7(2) . . . . ? C103 C102 N101 C115 -8.4(2) . . . . ? C123 C116 N101 C102 83.4(2) . . . . ? C117 C116 N101 C102 -153.06(19) . . . . ? C123 C116 N101 C115 -90.8(2) . . . . ? C117 C116 N101 C115 32.8(3) . . . . ? C109 C115 N101 C102 -15.1(2) . . . . ? C109 C115 N101 C116 159.37(19) . . . . ? C16 C17 O18 C19 169.22(17) . . . . ? C21 C19 O18 C17 179.31(18) . . . . ? C20 C19 O18 C17 60.8(2) . . . . ? C22 C19 O18 C17 -62.2(2) . . . . ? O23 C23 O24 C25 -4.6(3) . . . . ? C16 C23 O24 C25 176.07(17) . . . . ? C26 C25 O24 C23 -61.6(2) . . . . ? C27 C25 O24 C23 179.97(19) . . . . ? C28 C25 O24 C23 62.7(3) . . . . ? C116 C117 O118 C119 -165.18(17) . . . . ? C120 C119 O118 C117 -62.2(2) . . . . ? C121 C119 O118 C117 179.38(19) . . . . ? C122 C119 O118 C117 61.3(2) . . . . ? O123 C123 O124 C125 1.9(3) . . . . ? C116 C123 O124 C125 -178.75(17) . . . . ? C128 C125 O124 C123 62.5(3) . . . . ? C127 C125 O124 C123 -179.6(2) . . . . ? C126 C125 O124 C123 -61.8(3) . . . . ? Cl21 C200 Cl22 Cl2B 139.0(14) . . . . ? C200 Cl22 Cl2B Cl2A 9(21) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.092 _refine_diff_density_min -0.681 _refine_diff_density_rms 0.060 data_cu_nwn89_0ma _database_code_depnum_ccdc_archive 'CCDC 900341' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 N O4' _chemical_formula_weight 295.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 20.8667(4) _cell_length_b 5.20470(10) _cell_length_c 26.1797(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2843.24(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 127 _cell_measurement_theta_min 40.8 _cell_measurement_theta_max 130.9 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7529 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'ImuS-focus sealed tube' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'APEX II DUO' _diffrn_measurement_method omega/phi _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21209 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 66.64 _reflns_number_total 4961 _reflns_number_gt 4784 _reflns_threshold_expression >2sigma(I) _computing_data_collection COSMO _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. The absolute structure could not be determined because the compound is a weak anomalous scatterer (C,H,N,O) and the crystal was very small. The reflections for high theta values show less intensity. ; _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^)+(0.0363P)^2^+0.8759P] 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 0.46(14) _refine_ls_number_reflns 4961 _refine_ls_number_parameters 397 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 O4 O 0.62906(7) 0.6408(4) 0.00534(8) 0.0616(5) Uani 1 1 d . . . O7 O 0.42329(6) 0.2903(2) -0.07752(5) 0.0290(3) Uani 1 1 d . . . O8 O 0.35705(7) 0.0032(3) -0.10723(6) 0.0421(4) Uani 1 1 d . . . O17 O 0.39911(6) 0.7931(2) 0.01493(5) 0.0258(3) Uani 1 1 d . . . O104 O 0.13311(9) 0.1705(5) 0.28042(8) 0.0824(7) Uani 1 1 d . . . O107 O 0.34401(6) 0.5093(3) 0.35714(5) 0.0369(3) Uani 1 1 d . . . O108 O 0.40995(8) 0.8116(3) 0.38095(7) 0.0538(5) Uani 1 1 d . . . O111 O 0.35646(6) 0.0407(2) 0.25658(5) 0.0322(3) Uani 1 1 d . . . N10 N 0.32942(7) 0.4856(3) -0.01074(5) 0.0221(3) Uani 1 1 d . . . N110 N 0.42879(7) 0.3424(3) 0.28100(6) 0.0237(3) Uani 1 1 d . . . C1 C 0.44357(8) 0.4665(3) -0.03765(6) 0.0210(3) Uani 1 1 d . . . C2 C 0.48295(9) 0.6683(3) -0.06416(7) 0.0285(4) Uani 1 1 d . . . H2 H 0.4647 0.7592 -0.0921 0.034 Uiso 1 1 calc R . . C3 C 0.54229(10) 0.7233(4) -0.04981(8) 0.0353(5) Uani 1 1 d . . . H3 H 0.5646 0.8575 -0.0668 0.042 Uiso 1 1 calc R . . C4 C 0.57471(9) 0.5844(4) -0.00860(8) 0.0370(5) Uani 1 1 d . . . C5 C 0.53983(9) 0.3709(4) 0.01481(8) 0.0318(4) Uani 1 1 d . . . H5 H 0.5604 0.2710 0.0404 0.038 Uiso 1 1 calc R . . C6 C 0.48041(8) 0.3132(3) 0.00134(7) 0.0243(4) Uani 1 1 d . . . H6 H 0.4602 0.1695 0.0169 0.029 Uiso 1 1 calc R . . C8 C 0.36577(9) 0.1746(3) -0.07739(7) 0.0277(4) Uani 1 1 d . . . C9 C 0.31526(8) 0.2716(3) -0.04242(6) 0.0234(4) Uani 1 1 d . . . C11 C 0.38797(8) 0.5993(3) -0.00961(6) 0.0200(3) Uani 1 1 d . . . C12 C 0.27812(8) 0.5936(3) 0.02097(7) 0.0273(4) Uani 1 1 d . . . H12A H 0.2392 0.6149 -0.0003 0.033 Uiso 1 1 calc R . . H12B H 0.2913 0.7661 0.0329 0.033 Uiso 1 1 calc R . . C13 C 0.26161(8) 0.4294(3) 0.06699(7) 0.0241(4) Uani 1 1 d . . . C14 C 0.30406(10) 0.2635(5) 0.08966(8) 0.0429(5) Uani 1 1 d . . . H14 H 0.3459 0.2443 0.0760 0.052 Uiso 1 1 calc R . . C15 C 0.28607(12) 0.1229(5) 0.13269(8) 0.0481(6) Uani 1 1 d . . . H15 H 0.3157 0.0067 0.1478 0.058 Uiso 1 1 calc R . . C16 C 0.22707(11) 0.1502(4) 0.15316(8) 0.0424(5) Uani 1 1 d . . . H16 H 0.2155 0.0572 0.1830 0.051 Uiso 1 1 calc R . . C17 C 0.18427(13) 0.3126(6) 0.13064(11) 0.0655(8) Uani 1 1 d . . . H17 H 0.1424 0.3296 0.1445 0.079 Uiso 1 1 calc R . . C18 C 0.20127(11) 0.4529(5) 0.08776(9) 0.0510(6) Uani 1 1 d . . . H18 H 0.1711 0.5662 0.0726 0.061 Uiso 1 1 calc R . . C90 C 0.25827(9) 0.1585(4) -0.04391(7) 0.0321(4) Uani 1 1 d . . . H90A H 0.2244 0.2204 -0.0230 0.038 Uiso 1 1 calc R . . H90B H 0.2514 0.0158 -0.0658 0.038 Uiso 1 1 calc R . . C101 C 0.31890(8) 0.3492(3) 0.31640(7) 0.0243(4) Uani 1 1 d . . . C102 C 0.28217(10) 0.1429(4) 0.34309(8) 0.0364(5) Uani 1 1 d . . . H102 H 0.3029 0.0457 0.3690 0.044 Uiso 1 1 calc R . . C103 C 0.22212(11) 0.0909(4) 0.33204(8) 0.0417(6) Uani 1 1 d . . . H103 H 0.2012 -0.0451 0.3496 0.050 Uiso 1 1 calc R . . C104 C 0.18698(10) 0.2337(5) 0.29415(9) 0.0457(6) Uani 1 1 d . . . C105 C 0.21872(10) 0.4632(4) 0.27189(8) 0.0368(5) Uani 1 1 d . . . H105 H 0.1952 0.5731 0.2498 0.044 Uiso 1 1 calc R . . C106 C 0.27899(9) 0.5169(3) 0.28223(7) 0.0254(4) Uani 1 1 d . . . H106 H 0.2978 0.6661 0.2676 0.031 Uiso 1 1 calc R . . C108 C 0.39953(9) 0.6388(4) 0.35166(7) 0.0320(4) Uani 1 1 d . . . C109 C 0.44573(9) 0.5528(3) 0.31251(6) 0.0250(4) Uani 1 1 d . . . C111 C 0.37084(8) 0.2273(3) 0.28249(7) 0.0242(4) Uani 1 1 d . . . C112 C 0.47610(9) 0.2516(3) 0.24308(8) 0.0283(4) Uani 1 1 d . . . H11A H 0.4625 0.0822 0.2297 0.034 Uiso 1 1 calc R . . H11B H 0.5182 0.2292 0.2600 0.034 Uiso 1 1 calc R . . C113 C 0.48317(8) 0.4375(3) 0.19913(7) 0.0247(4) Uani 1 1 d . . . C114 C 0.54332(10) 0.5115(5) 0.18280(8) 0.0425(5) Uani 1 1 d . . . H114 H 0.5802 0.4479 0.1999 0.051 Uiso 1 1 calc R . . C115 C 0.55061(13) 0.6771(5) 0.14184(9) 0.0573(7) Uani 1 1 d . . . H115 H 0.5923 0.7243 0.1307 0.069 Uiso 1 1 calc R . . C116 C 0.49797(15) 0.7724(5) 0.11754(8) 0.0566(7) Uani 1 1 d . . . H116 H 0.5028 0.8881 0.0897 0.068 Uiso 1 1 calc R . . C117 C 0.43812(14) 0.7006(6) 0.13340(9) 0.0665(9) Uani 1 1 d . . . H117 H 0.4013 0.7645 0.1162 0.080 Uiso 1 1 calc R . . C118 C 0.43105(10) 0.5363(5) 0.17409(8) 0.0485(6) Uani 1 1 d . . . H118 H 0.3892 0.4903 0.1851 0.058 Uiso 1 1 calc R . . C190 C 0.50188(10) 0.6714(4) 0.31054(7) 0.0340(4) Uani 1 1 d . . . H19A H 0.5336 0.6162 0.2869 0.041 Uiso 1 1 calc R . . H19B H 0.5104 0.8118 0.3327 0.041 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 O4 0.0296(8) 0.0790(12) 0.0761(12) -0.0213(10) 0.0007(8) -0.0206(8) O7 0.0278(6) 0.0336(7) 0.0257(6) -0.0096(5) 0.0002(5) 0.0009(5) O8 0.0430(9) 0.0430(8) 0.0402(8) -0.0180(7) -0.0133(6) 0.0024(7) O17 0.0279(6) 0.0214(6) 0.0280(6) -0.0022(5) 0.0048(5) -0.0031(5) O104 0.0417(10) 0.140(2) 0.0652(12) -0.0395(13) 0.0083(9) -0.0457(12) O107 0.0278(7) 0.0524(8) 0.0303(7) -0.0182(6) 0.0017(5) 0.0076(6) O108 0.0399(8) 0.0655(11) 0.0561(10) -0.0382(9) -0.0172(7) 0.0129(8) O111 0.0355(7) 0.0252(6) 0.0357(7) -0.0073(5) 0.0145(6) -0.0083(5) N10 0.0188(7) 0.0209(7) 0.0266(7) 0.0017(6) 0.0023(6) -0.0007(6) N110 0.0240(7) 0.0200(7) 0.0273(7) 0.0000(6) 0.0067(6) 0.0015(6) C1 0.0206(8) 0.0202(8) 0.0223(8) -0.0003(7) 0.0010(6) -0.0013(7) C2 0.0343(10) 0.0196(8) 0.0314(9) 0.0076(7) 0.0169(8) 0.0068(8) C3 0.0372(11) 0.0220(8) 0.0468(11) -0.0034(8) 0.0232(9) -0.0061(8) C4 0.0231(9) 0.0399(11) 0.0480(12) -0.0139(10) 0.0053(8) -0.0081(8) C5 0.0272(9) 0.0341(10) 0.0342(10) -0.0015(8) -0.0042(8) 0.0038(8) C6 0.0278(9) 0.0178(8) 0.0274(9) 0.0016(6) 0.0035(7) 0.0000(7) C8 0.0297(9) 0.0278(9) 0.0255(8) -0.0004(7) -0.0088(7) 0.0022(8) C9 0.0258(9) 0.0226(8) 0.0217(8) 0.0055(7) -0.0071(7) -0.0022(7) C11 0.0209(8) 0.0194(8) 0.0198(8) 0.0025(7) 0.0006(6) -0.0015(7) C12 0.0206(8) 0.0227(9) 0.0384(10) 0.0049(8) 0.0068(7) 0.0023(7) C13 0.0248(9) 0.0211(8) 0.0265(8) -0.0028(7) 0.0034(7) -0.0017(7) C14 0.0339(10) 0.0562(13) 0.0387(11) 0.0133(10) 0.0127(9) 0.0166(10) C15 0.0542(14) 0.0540(14) 0.0362(11) 0.0141(10) 0.0103(10) 0.0218(11) C16 0.0548(13) 0.0467(12) 0.0257(10) 0.0039(9) 0.0124(9) 0.0021(11) C17 0.0491(14) 0.091(2) 0.0566(15) 0.0276(15) 0.0297(13) 0.0206(14) C18 0.0354(11) 0.0670(15) 0.0505(13) 0.0208(12) 0.0151(10) 0.0192(11) C90 0.0312(10) 0.0368(10) 0.0282(9) 0.0045(8) -0.0081(8) -0.0091(8) C101 0.0232(8) 0.0241(8) 0.0255(8) -0.0031(7) 0.0070(7) 0.0023(7) C102 0.0449(12) 0.0258(9) 0.0387(10) 0.0062(8) 0.0256(9) 0.0097(9) C103 0.0485(13) 0.0250(9) 0.0516(13) -0.0078(9) 0.0335(10) -0.0070(9) C104 0.0279(10) 0.0621(14) 0.0470(13) -0.0289(11) 0.0158(9) -0.0229(10) C105 0.0332(10) 0.0456(11) 0.0316(10) -0.0066(9) -0.0028(8) 0.0054(9) C106 0.0290(9) 0.0198(8) 0.0276(9) -0.0013(7) 0.0039(7) -0.0023(7) C108 0.0277(10) 0.0354(10) 0.0330(10) -0.0112(9) -0.0115(8) 0.0108(8) C109 0.0268(9) 0.0244(9) 0.0238(9) 0.0018(7) -0.0074(7) 0.0069(7) C111 0.0261(9) 0.0221(8) 0.0245(8) 0.0005(7) 0.0078(7) 0.0012(7) C112 0.0256(9) 0.0227(8) 0.0366(10) 0.0004(8) 0.0137(8) 0.0041(7) C113 0.0266(9) 0.0237(8) 0.0238(8) -0.0047(7) 0.0037(7) 0.0014(7) C114 0.0289(11) 0.0612(14) 0.0375(11) 0.0173(10) -0.0021(8) -0.0086(10) C115 0.0615(15) 0.0773(17) 0.0330(11) 0.0183(12) -0.0004(10) -0.0336(14) C116 0.100(2) 0.0484(13) 0.0216(10) 0.0082(10) 0.0037(12) 0.0118(14) C117 0.0784(19) 0.097(2) 0.0238(11) 0.0106(12) 0.0085(12) 0.0559(17) C118 0.0346(11) 0.0838(17) 0.0270(10) 0.0023(11) 0.0080(9) 0.0218(12) C190 0.0323(10) 0.0414(11) 0.0282(9) 0.0039(8) -0.0100(8) -0.0046(9) _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 O4 C4 1.227(3) . ? O7 C8 1.343(2) . ? O7 C1 1.453(2) . ? O8 C8 1.200(2) . ? O17 C11 1.219(2) . ? O104 C104 1.225(3) . ? O107 C108 1.348(2) . ? O107 C101 1.451(2) . ? O108 C108 1.201(2) . ? O111 C111 1.222(2) . ? N10 C11 1.358(2) . ? N10 C9 1.420(2) . ? N10 C12 1.467(2) . ? N110 C111 1.350(2) . ? N110 C109 1.416(2) . ? N110 C112 1.477(2) . ? C1 C2 1.503(2) . ? C1 C6 1.507(2) . ? C1 C11 1.537(2) . ? C2 C3 1.325(3) . ? C2 H2 0.9500 . ? C3 C4 1.464(3) . ? C3 H3 0.9500 . ? C4 C5 1.463(3) . ? C5 C6 1.323(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.485(3) . ? C9 C90 1.327(3) . ? C12 C13 1.517(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.372(3) . ? C13 C18 1.377(3) . ? C14 C15 1.395(3) . ? C14 H14 0.9500 . ? C15 C16 1.350(3) . ? C15 H15 0.9500 . ? C16 C17 1.364(3) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C90 H90A 0.9500 . ? C90 H90B 0.9500 . ? C101 C102 1.493(3) . ? C101 C106 1.502(3) . ? C101 C111 1.538(2) . ? C102 C103 1.314(3) . ? C102 H102 0.9500 . ? C103 C104 1.440(4) . ? C103 H103 0.9500 . ? C104 C105 1.485(3) . ? C105 C106 1.316(3) . ? C105 H105 0.9500 . ? C106 H106 0.9500 . ? C108 C109 1.477(3) . ? C109 C190 1.326(3) . ? C112 C113 1.511(3) . ? C112 H11A 0.9900 . ? C112 H11B 0.9900 . ? C113 C118 1.370(3) . ? C113 C114 1.381(3) . ? C114 C115 1.384(3) . ? C114 H114 0.9500 . ? C115 C116 1.363(4) . ? C115 H115 0.9500 . ? C116 C117 1.368(4) . ? C116 H116 0.9500 . ? C117 C118 1.374(4) . ? C117 H117 0.9500 . ? C118 H118 0.9500 . ? C190 H19A 0.9500 . ? C190 H19B 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 C8 O7 C1 122.80(13) . . ? C108 O107 C101 121.28(14) . . ? C11 N10 C9 122.80(14) . . ? C11 N10 C12 118.52(14) . . ? C9 N10 C12 118.66(14) . . ? C111 N110 C109 123.35(15) . . ? C111 N110 C112 118.43(14) . . ? C109 N110 C112 118.17(14) . . ? O7 C1 C2 105.58(14) . . ? O7 C1 C6 107.52(13) . . ? C2 C1 C6 113.83(15) . . ? O7 C1 C11 114.03(13) . . ? C2 C1 C11 108.61(13) . . ? C6 C1 C11 107.44(13) . . ? C3 C2 C1 122.06(17) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 122.26(17) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? O4 C4 C5 121.1(2) . . ? O4 C4 C3 121.9(2) . . ? C5 C4 C3 116.99(17) . . ? C6 C5 C4 121.80(18) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 122.57(16) . . ? C5 C6 H6 118.7 . . ? C1 C6 H6 118.7 . . ? O8 C8 O7 117.86(17) . . ? O8 C8 C9 123.14(17) . . ? O7 C8 C9 118.93(15) . . ? C90 C9 N10 123.46(17) . . ? C90 C9 C8 117.85(17) . . ? N10 C9 C8 118.64(15) . . ? O17 C11 N10 122.95(15) . . ? O17 C11 C1 118.69(14) . . ? N10 C11 C1 118.23(14) . . ? N10 C12 C13 113.53(14) . . ? N10 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N10 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C18 118.39(18) . . ? C14 C13 C12 123.47(16) . . ? C18 C13 C12 118.12(17) . . ? C13 C14 C15 120.38(19) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.4(2) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 120.6(2) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.5(2) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C9 C90 H90A 120.0 . . ? C9 C90 H90B 120.0 . . ? H90A C90 H90B 120.0 . . ? O107 C101 C102 104.73(16) . . ? O107 C101 C106 107.70(14) . . ? C102 C101 C106 114.34(16) . . ? O107 C101 C111 113.99(14) . . ? C102 C101 C111 109.60(14) . . ? C106 C101 C111 106.66(15) . . ? C103 C102 C101 122.3(2) . . ? C103 C102 H102 118.8 . . ? C101 C102 H102 118.8 . . ? C102 C103 C104 122.08(18) . . ? C102 C103 H103 119.0 . . ? C104 C103 H103 119.0 . . ? O104 C104 C103 122.1(2) . . ? O104 C104 C105 120.7(3) . . ? C103 C104 C105 117.27(17) . . ? C106 C105 C104 121.1(2) . . ? C106 C105 H105 119.5 . . ? C104 C105 H105 119.5 . . ? C105 C106 C101 121.92(17) . . ? C105 C106 H106 119.0 . . ? C101 C106 H106 119.0 . . ? O108 C108 O107 117.52(18) . . ? O108 C108 C109 123.48(19) . . ? O107 C108 C109 118.89(15) . . ? C190 C109 N110 123.94(17) . . ? C190 C109 C108 117.57(17) . . ? N110 C109 C108 118.43(16) . . ? O111 C111 N110 123.81(16) . . ? O111 C111 C101 118.36(16) . . ? N110 C111 C101 117.72(15) . . ? N110 C112 C113 111.84(14) . . ? N110 C112 H11A 109.2 . . ? C113 C112 H11A 109.2 . . ? N110 C112 H11B 109.2 . . ? C113 C112 H11B 109.2 . . ? H11A C112 H11B 107.9 . . ? C118 C113 C114 117.96(19) . . ? C118 C113 C112 121.83(18) . . ? C114 C113 C112 120.21(17) . . ? C113 C114 C115 120.9(2) . . ? C113 C114 H114 119.6 . . ? C115 C114 H114 119.6 . . ? C116 C115 C114 120.0(2) . . ? C116 C115 H115 120.0 . . ? C114 C115 H115 120.0 . . ? C115 C116 C117 119.6(2) . . ? C115 C116 H116 120.2 . . ? C117 C116 H116 120.2 . . ? C116 C117 C118 120.2(2) . . ? C116 C117 H117 119.9 . . ? C118 C117 H117 119.9 . . ? C113 C118 C117 121.3(2) . . ? C113 C118 H118 119.4 . . ? C117 C118 H118 119.4 . . ? C109 C190 H19A 120.0 . . ? C109 C190 H19B 120.0 . . ? H19A C190 H19B 120.0 . . ? 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 C8 O7 C1 C2 -144.29(16) . . . . ? C8 O7 C1 C6 93.85(18) . . . . ? C8 O7 C1 C11 -25.1(2) . . . . ? O7 C1 C2 C3 -125.13(18) . . . . ? C6 C1 C2 C3 -7.4(2) . . . . ? C11 C1 C2 C3 112.19(19) . . . . ? C1 C2 C3 C4 2.7(3) . . . . ? C2 C3 C4 O4 -178.09(19) . . . . ? C2 C3 C4 C5 3.0(3) . . . . ? O4 C4 C5 C6 177.72(19) . . . . ? C3 C4 C5 C6 -3.3(3) . . . . ? C4 C5 C6 C1 -1.9(3) . . . . ? O7 C1 C6 C5 123.67(18) . . . . ? C2 C1 C6 C5 7.1(2) . . . . ? C11 C1 C6 C5 -113.19(19) . . . . ? C1 O7 C8 O8 -168.63(16) . . . . ? C1 O7 C8 C9 14.2(2) . . . . ? C11 N10 C9 C90 179.98(16) . . . . ? C12 N10 C9 C90 -2.0(2) . . . . ? C11 N10 C9 C8 -2.6(2) . . . . ? C12 N10 C9 C8 175.45(15) . . . . ? O8 C8 C9 C90 1.3(3) . . . . ? O7 C8 C9 C90 178.29(16) . . . . ? O8 C8 C9 N10 -176.24(17) . . . . ? O7 C8 C9 N10 0.7(2) . . . . ? C9 N10 C11 O17 174.97(15) . . . . ? C12 N10 C11 O17 -3.1(2) . . . . ? C9 N10 C11 C1 -9.3(2) . . . . ? C12 N10 C11 C1 172.64(14) . . . . ? O7 C1 C11 O17 -161.97(14) . . . . ? C2 C1 C11 O17 -44.5(2) . . . . ? C6 C1 C11 O17 78.99(18) . . . . ? O7 C1 C11 N10 22.1(2) . . . . ? C2 C1 C11 N10 139.54(16) . . . . ? C6 C1 C11 N10 -96.92(17) . . . . ? C11 N10 C12 C13 -107.48(17) . . . . ? C9 N10 C12 C13 74.4(2) . . . . ? N10 C12 C13 C14 25.9(3) . . . . ? N10 C12 C13 C18 -155.67(19) . . . . ? C18 C13 C14 C15 0.0(3) . . . . ? C12 C13 C14 C15 178.4(2) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C14 C15 C16 C17 1.6(4) . . . . ? C15 C16 C17 C18 -1.3(4) . . . . ? C14 C13 C18 C17 0.3(4) . . . . ? C12 C13 C18 C17 -178.3(3) . . . . ? C16 C17 C18 C13 0.4(5) . . . . ? C108 O107 C101 C102 150.41(16) . . . . ? C108 O107 C101 C106 -87.50(19) . . . . ? C108 O107 C101 C111 30.6(2) . . . . ? O107 C101 C102 C103 126.67(19) . . . . ? C106 C101 C102 C103 9.0(3) . . . . ? C111 C101 C102 C103 -110.7(2) . . . . ? C101 C102 C103 C104 -1.5(3) . . . . ? C102 C103 C104 O104 173.0(2) . . . . ? C102 C103 C104 C105 -6.9(3) . . . . ? O104 C104 C105 C106 -172.6(2) . . . . ? C103 C104 C105 C106 7.3(3) . . . . ? C104 C105 C106 C101 0.6(3) . . . . ? O107 C101 C106 C105 -124.42(18) . . . . ? C102 C101 C106 C105 -8.5(2) . . . . ? C111 C101 C106 C105 112.8(2) . . . . ? C101 O107 C108 O108 162.81(18) . . . . ? C101 O107 C108 C109 -20.8(3) . . . . ? C111 N110 C109 C190 -178.28(17) . . . . ? C112 N110 C109 C190 -0.9(2) . . . . ? C111 N110 C109 C108 4.7(2) . . . . ? C112 N110 C109 C108 -177.96(15) . . . . ? O108 C108 C109 C190 1.1(3) . . . . ? O107 C108 C109 C190 -175.05(17) . . . . ? O108 C108 C109 N110 178.33(18) . . . . ? O107 C108 C109 N110 2.2(2) . . . . ? C109 N110 C111 O111 -177.64(16) . . . . ? C112 N110 C111 O111 5.0(3) . . . . ? C109 N110 C111 C101 6.2(2) . . . . ? C112 N110 C111 C101 -171.12(15) . . . . ? O107 C101 C111 O111 160.91(16) . . . . ? C102 C101 C111 O111 43.9(2) . . . . ? C106 C101 C111 O111 -80.37(19) . . . . ? O107 C101 C111 N110 -22.8(2) . . . . ? C102 C101 C111 N110 -139.76(17) . . . . ? C106 C101 C111 N110 95.96(18) . . . . ? C111 N110 C112 C113 105.38(18) . . . . ? C109 N110 C112 C113 -72.1(2) . . . . ? N110 C112 C113 C118 -48.2(2) . . . . ? N110 C112 C113 C114 132.21(19) . . . . ? C118 C113 C114 C115 -1.0(3) . . . . ? C112 C113 C114 C115 178.5(2) . . . . ? C113 C114 C115 C116 1.0(4) . . . . ? C114 C115 C116 C117 -0.9(4) . . . . ? C115 C116 C117 C118 1.0(4) . . . . ? C114 C113 C118 C117 1.1(3) . . . . ? C112 C113 C118 C117 -178.5(2) . . . . ? C116 C117 C118 C113 -1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 66.64 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.290 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.033