# Electronic Supplementary Material (ESI) for CrystEngComm # 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_formIabscor _database_code_depnum_ccdc_archive 'CCDC 892946' #TrackingRef 'form1abscor.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 Cl N O5' _chemical_formula_weight 373.78 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' Cl Cl 0.1484 0.1585 '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 7.7265(16) _cell_length_b 9.864(2) _cell_length_c 22.541(5) _cell_angle_alpha 79.457(4) _cell_angle_beta 89.924(7) _cell_angle_gamma 89.993(4) _cell_volume 1688.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7270 _cell_measurement_theta_min 0.92 _cell_measurement_theta_max 33.72 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8797 _exptl_absorpt_correction_T_max 0.8928 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12503 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0990 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 0.92 _diffrn_reflns_theta_max 33.72 _reflns_number_total 12496 _reflns_number_gt 7270 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 Following ALERTS were generated <<< #------------------------------------------ Format: alert-number_ALERT_alert-type_alert-level text PLAT022_ALERT_3_G Ratio Unique / Expected Reflections (too) Low .. 0.927 The model is complete and looks reasonable. We suspect this is due to the crystal having been a non-merohedral twin. ; _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^)+(0.0495P)^2^+0.2630P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12503 _refine_ls_number_parameters 476 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1270 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 Cl1A Cl -0.06505(10) -0.08316(6) 0.31819(3) 0.03602(16) Uani 1 1 d . . . C2A C -0.0372(3) 0.0204(2) 0.24716(10) 0.0247(5) Uani 1 1 d . . . C3A C -0.0661(3) -0.0354(2) 0.19625(11) 0.0254(5) Uani 1 1 d . . . H3A H -0.1039 -0.1282 0.1997 0.030 Uiso 1 1 calc R . . C4A C -0.0391(3) 0.0466(2) 0.13956(11) 0.0243(5) Uani 1 1 d . . . H4A H -0.0563 0.0086 0.1042 0.029 Uiso 1 1 calc R . . C5A C 0.0130(3) 0.1836(2) 0.13439(10) 0.0210(4) Uani 1 1 d . . . C6A C 0.0424(3) 0.2364(2) 0.18663(11) 0.0258(5) Uani 1 1 d . . . H6A H 0.0807 0.3289 0.1836 0.031 Uiso 1 1 calc R . . C7A C 0.0166(3) 0.1554(2) 0.24314(11) 0.0284(5) Uani 1 1 d . . . H7A H 0.0356 0.1924 0.2787 0.034 Uiso 1 1 calc R . . C8A C 0.0597(3) 0.2742(2) 0.07554(10) 0.0200(4) Uani 1 1 d . . . O9A O 0.1886(2) 0.34798(16) 0.07286(7) 0.0255(3) Uani 1 1 d . . . N10A N -0.0381(2) 0.27218(17) 0.02482(8) 0.0190(4) Uani 1 1 d . . . C11A C 0.0281(3) 0.3199(2) -0.03500(10) 0.0178(4) Uani 1 1 d . . . C12A C 0.1996(3) 0.3487(2) -0.05400(10) 0.0214(4) Uani 1 1 d . . . H12A H 0.2906 0.3457 -0.0255 0.026 Uiso 1 1 calc R . . C13A C 0.2324(3) 0.3816(2) -0.11549(11) 0.0245(5) Uani 1 1 d . . . H13A H 0.3478 0.4008 -0.1291 0.029 Uiso 1 1 calc R . . C14A C 0.1001(3) 0.3870(2) -0.15778(10) 0.0234(5) Uani 1 1 d . . . O15A O 0.1533(2) 0.41699(19) -0.21724(8) 0.0334(4) Uani 1 1 d . . . C16A C 0.0226(4) 0.4279(3) -0.26188(12) 0.0379(6) Uani 1 1 d . . . H16A H -0.0364 0.3390 -0.2589 0.057 Uiso 1 1 calc R . . H16B H 0.0752 0.4537 -0.3020 0.057 Uiso 1 1 calc R . . H16C H -0.0612 0.4985 -0.2557 0.057 Uiso 1 1 calc R . . C17A C -0.0709(3) 0.3612(2) -0.13848(10) 0.0227(4) Uani 1 1 d . . . H17A H -0.1626 0.3663 -0.1668 0.027 Uiso 1 1 calc R . . C18A C -0.1033(3) 0.3278(2) -0.07658(10) 0.0192(4) Uani 1 1 d . . . C19A C -0.2762(3) 0.2965(2) -0.04498(10) 0.0194(4) Uani 1 1 d . . . O20A O -0.38295(19) 0.41398(15) -0.04854(8) 0.0248(3) Uani 1 1 d . . . H20A H -0.3209 0.4847 -0.0510 0.037 Uiso 1 1 calc R . . C21A C -0.3770(3) 0.1815(2) -0.06544(11) 0.0221(5) Uani 1 1 d . . . H21B H -0.5023 0.1898 -0.0574 0.027 Uiso 1 1 calc R . . H21A H -0.3599 0.1833 -0.1091 0.027 Uiso 1 1 calc R . . C22A C -0.3043(3) 0.0519(2) -0.02876(10) 0.0217(4) Uani 1 1 d . . . O23A O -0.3143(2) -0.06456(16) -0.03708(8) 0.0309(4) Uani 1 1 d . . . O24A O -0.2207(2) 0.08167(15) 0.02004(7) 0.0227(3) Uani 1 1 d . . . C25A C -0.2198(3) 0.2301(2) 0.02067(10) 0.0187(4) Uani 1 1 d . . . C26A C -0.3414(3) 0.2611(2) 0.06973(11) 0.0258(5) Uani 1 1 d . . . H26A H -0.4606 0.2401 0.0597 0.039 Uiso 1 1 calc R . . H26B H -0.3324 0.3588 0.0725 0.039 Uiso 1 1 calc R . . H26C H -0.3093 0.2043 0.1085 0.039 Uiso 1 1 calc R . . Cl1B Cl 0.57117(11) 0.02092(7) 0.80582(3) 0.04167(18) Uani 1 1 d . . . C2B C 0.5373(3) 0.1059(2) 0.73205(11) 0.0273(5) Uani 1 1 d . . . C3B C 0.5519(3) 0.0311(2) 0.68568(11) 0.0257(5) Uani 1 1 d . . . H3B H 0.5813 -0.0640 0.6943 0.031 Uiso 1 1 calc R . . C4B C 0.5230(3) 0.0966(2) 0.62667(10) 0.0227(5) Uani 1 1 d . . . H4B H 0.5304 0.0459 0.5948 0.027 Uiso 1 1 calc R . . C5B C 0.4831(3) 0.2371(2) 0.61406(10) 0.0197(4) Uani 1 1 d . . . C6B C 0.4675(3) 0.3093(2) 0.66170(11) 0.0274(5) Uani 1 1 d . . . H6B H 0.4370 0.4042 0.6534 0.033 Uiso 1 1 calc R . . C7B C 0.4955(3) 0.2449(2) 0.72047(12) 0.0311(6) Uani 1 1 d . . . H7B H 0.4864 0.2950 0.7525 0.037 Uiso 1 1 calc R . . C8B C 0.4404(3) 0.3113(2) 0.55208(10) 0.0187(4) Uani 1 1 d . . . O9B O 0.3167(2) 0.39097(16) 0.54386(7) 0.0248(3) Uani 1 1 d . . . N10B N 0.5369(2) 0.28466(17) 0.50342(8) 0.0182(4) Uani 1 1 d . . . C11B C 0.4756(3) 0.31400(19) 0.44294(10) 0.0174(4) Uani 1 1 d . . . C12B C 0.3057(3) 0.3401(2) 0.42311(10) 0.0206(4) Uani 1 1 d . . . H12B H 0.2143 0.3475 0.4506 0.025 Uiso 1 1 calc R . . C13B C 0.2763(3) 0.3547(2) 0.36181(10) 0.0234(5) Uani 1 1 d . . . H13B H 0.1618 0.3721 0.3471 0.028 Uiso 1 1 calc R . . C14B C 0.4106(3) 0.3447(2) 0.32039(10) 0.0223(5) Uani 1 1 d . . . O15B O 0.3609(2) 0.36025(19) 0.26129(8) 0.0327(4) Uani 1 1 d . . . C16B C 0.4925(4) 0.3503(3) 0.21684(12) 0.0385(6) Uani 1 1 d . . . H16D H 0.5457 0.2586 0.2256 0.058 Uiso 1 1 calc R . . H16F H 0.5811 0.4207 0.2181 0.058 Uiso 1 1 calc R . . H16E H 0.4399 0.3647 0.1766 0.058 Uiso 1 1 calc R . . C17B C 0.5797(3) 0.3206(2) 0.34042(10) 0.0199(4) Uani 1 1 d . . . H17B H 0.6719 0.3142 0.3131 0.024 Uiso 1 1 calc R . . C18B C 0.6085(3) 0.3060(2) 0.40217(10) 0.0174(4) Uani 1 1 d . . . C19B C 0.7800(3) 0.2845(2) 0.43423(10) 0.0170(4) Uani 1 1 d . . . O20B O 0.88714(19) 0.40277(15) 0.42180(7) 0.0216(3) Uani 1 1 d . . . H20B H 0.8323 0.4716 0.4289 0.032 Uiso 1 1 calc R . . C21B C 0.8811(3) 0.1594(2) 0.42237(10) 0.0211(4) Uani 1 1 d . . . H21C H 0.8610 0.1436 0.3808 0.025 Uiso 1 1 calc R . . H21D H 1.0067 0.1714 0.4283 0.025 Uiso 1 1 calc R . . C22B C 0.8105(3) 0.0426(2) 0.46809(10) 0.0204(4) Uani 1 1 d . . . O23B O 0.8242(2) -0.08007(15) 0.46945(8) 0.0289(4) Uani 1 1 d . . . O24B O 0.7244(2) 0.09081(14) 0.51284(7) 0.0216(3) Uani 1 1 d . . . C25B C 0.7203(3) 0.2422(2) 0.50241(10) 0.0180(4) Uani 1 1 d . . . C26B C 0.8378(3) 0.2937(2) 0.54650(10) 0.0229(5) Uani 1 1 d . . . H26D H 0.9583 0.2734 0.5376 0.034 Uiso 1 1 calc R . . H26F H 0.8087 0.2477 0.5876 0.034 Uiso 1 1 calc R . . H26E H 0.8232 0.3935 0.5430 0.034 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 Cl1A 0.0517(4) 0.0319(3) 0.0224(3) 0.0004(2) 0.0022(3) -0.0033(3) C2A 0.0283(12) 0.0246(11) 0.0196(11) 0.0000(9) 0.0004(9) 0.0005(9) C3A 0.0316(13) 0.0197(10) 0.0246(12) -0.0033(9) -0.0010(10) -0.0016(9) C4A 0.0312(13) 0.0202(10) 0.0222(12) -0.0052(9) -0.0038(9) -0.0017(9) C5A 0.0199(11) 0.0200(10) 0.0228(12) -0.0028(8) -0.0014(9) -0.0018(8) C6A 0.0318(13) 0.0203(10) 0.0257(12) -0.0048(9) -0.0020(10) -0.0059(9) C7A 0.0369(14) 0.0288(12) 0.0220(13) -0.0110(10) 0.0009(10) -0.0025(10) C8A 0.0216(11) 0.0169(9) 0.0225(11) -0.0058(8) -0.0001(9) -0.0003(8) O9A 0.0273(9) 0.0220(8) 0.0274(9) -0.0048(7) -0.0018(7) -0.0068(7) N10A 0.0174(9) 0.0188(8) 0.0202(9) -0.0022(7) -0.0008(7) -0.0029(7) C11A 0.0193(10) 0.0145(9) 0.0189(11) -0.0014(8) -0.0011(8) -0.0002(7) C12A 0.0188(11) 0.0222(10) 0.0223(12) -0.0021(9) -0.0002(9) 0.0008(8) C13A 0.0190(11) 0.0247(11) 0.0279(13) 0.0001(9) 0.0029(9) 0.0011(9) C14A 0.0277(12) 0.0209(10) 0.0207(12) -0.0014(9) 0.0023(9) 0.0028(9) O15A 0.0319(10) 0.0435(10) 0.0225(9) 0.0001(8) 0.0033(7) 0.0014(8) C16A 0.0430(16) 0.0484(16) 0.0201(13) -0.0006(11) -0.0022(11) 0.0111(13) C17A 0.0239(11) 0.0203(10) 0.0224(11) 0.0000(8) -0.0043(9) 0.0023(8) C18A 0.0197(10) 0.0160(9) 0.0218(11) -0.0034(8) -0.0003(8) -0.0001(8) C19A 0.0174(10) 0.0161(9) 0.0248(12) -0.0039(8) -0.0027(8) 0.0006(8) O20A 0.0177(8) 0.0162(7) 0.0397(10) -0.0029(7) -0.0015(7) -0.0004(6) C21A 0.0207(11) 0.0179(10) 0.0280(13) -0.0046(9) -0.0027(9) -0.0022(8) C22A 0.0199(11) 0.0206(10) 0.0251(12) -0.0058(9) 0.0036(9) -0.0034(8) O23A 0.0348(10) 0.0189(8) 0.0407(11) -0.0096(7) -0.0019(8) -0.0027(7) O24A 0.0256(8) 0.0152(7) 0.0265(9) -0.0020(6) -0.0031(7) -0.0020(6) C25A 0.0201(11) 0.0153(9) 0.0215(11) -0.0054(8) -0.0006(8) -0.0022(8) C26A 0.0218(12) 0.0288(12) 0.0274(13) -0.0066(10) 0.0038(9) -0.0012(9) Cl1B 0.0638(5) 0.0394(3) 0.0213(3) -0.0040(3) -0.0073(3) 0.0060(3) C2B 0.0334(13) 0.0284(11) 0.0199(12) -0.0040(9) -0.0023(10) 0.0017(10) C3B 0.0327(13) 0.0199(10) 0.0244(12) -0.0040(9) -0.0001(10) 0.0020(9) C4B 0.0281(12) 0.0202(10) 0.0208(12) -0.0059(9) 0.0040(9) 0.0002(9) C5B 0.0192(10) 0.0210(10) 0.0194(11) -0.0051(8) 0.0030(8) -0.0003(8) C6B 0.0338(13) 0.0203(10) 0.0296(13) -0.0081(9) -0.0013(10) 0.0035(9) C7B 0.0421(15) 0.0286(12) 0.0256(13) -0.0127(10) -0.0027(11) 0.0035(10) C8B 0.0198(10) 0.0158(9) 0.0216(11) -0.0063(8) 0.0012(8) -0.0007(8) O9B 0.0233(8) 0.0238(8) 0.0284(9) -0.0079(7) -0.0009(7) 0.0083(6) N10B 0.0148(8) 0.0193(8) 0.0202(9) -0.0030(7) -0.0017(7) 0.0035(7) C11B 0.0192(10) 0.0133(8) 0.0187(11) -0.0006(7) -0.0015(8) 0.0003(7) C12B 0.0166(10) 0.0208(10) 0.0247(12) -0.0049(9) 0.0001(8) 0.0024(8) C13B 0.0192(11) 0.0261(11) 0.0242(12) -0.0029(9) -0.0058(9) 0.0011(9) C14B 0.0262(12) 0.0195(10) 0.0211(11) -0.0027(8) -0.0052(9) -0.0008(8) O15B 0.0287(9) 0.0486(11) 0.0208(9) -0.0066(8) -0.0049(7) -0.0010(8) C16B 0.0415(16) 0.0538(17) 0.0188(13) -0.0034(12) 0.0013(11) -0.0100(13) C17B 0.0203(11) 0.0203(10) 0.0193(11) -0.0039(8) -0.0005(8) 0.0002(8) C18B 0.0175(10) 0.0144(9) 0.0203(11) -0.0031(8) -0.0013(8) 0.0013(7) C19B 0.0148(10) 0.0145(9) 0.0216(11) -0.0029(8) 0.0006(8) 0.0040(7) O20B 0.0178(8) 0.0166(7) 0.0306(9) -0.0046(6) 0.0026(6) 0.0013(6) C21B 0.0197(11) 0.0212(10) 0.0230(12) -0.0056(9) 0.0007(8) 0.0057(8) C22B 0.0173(10) 0.0217(10) 0.0233(12) -0.0071(9) -0.0040(8) 0.0034(8) O23B 0.0328(10) 0.0172(7) 0.0374(11) -0.0066(7) -0.0015(8) 0.0056(7) O24B 0.0236(8) 0.0161(7) 0.0241(8) -0.0012(6) 0.0008(6) 0.0046(6) C25B 0.0181(10) 0.0139(9) 0.0219(11) -0.0034(8) -0.0017(8) 0.0054(7) C26B 0.0198(11) 0.0260(11) 0.0238(12) -0.0070(9) -0.0052(9) 0.0030(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 Cl1A C2A 1.747(2) . ? C2A C3A 1.379(3) . ? C2A C7A 1.382(3) . ? C3A C4A 1.397(3) . ? C4A C5A 1.394(3) . ? C5A C6A 1.391(3) . ? C5A C8A 1.501(3) . ? C6A C7A 1.388(3) . ? C8A O9A 1.228(3) . ? C8A N10A 1.375(3) . ? N10A C11A 1.438(3) . ? N10A C25A 1.472(3) . ? C11A C18A 1.375(3) . ? C11A C12A 1.405(3) . ? C12A C13A 1.388(3) . ? C13A C14A 1.393(3) . ? C14A O15A 1.381(3) . ? C14A C17A 1.399(3) . ? O15A C16A 1.416(3) . ? C17A C18A 1.396(3) . ? C18A C19A 1.518(3) . ? C19A O20A 1.412(2) . ? C19A C21A 1.516(3) . ? C19A C25A 1.567(3) . ? C21A C22A 1.500(3) . ? C22A O23A 1.200(3) . ? C22A O24A 1.354(3) . ? O24A C25A 1.467(2) . ? C25A C26A 1.523(3) . ? Cl1B C2B 1.740(2) . ? C2B C7B 1.387(3) . ? C2B C3B 1.390(3) . ? C3B C4B 1.387(3) . ? C4B C5B 1.397(3) . ? C5B C6B 1.398(3) . ? C5B C8B 1.491(3) . ? C6B C7B 1.378(3) . ? C8B O9B 1.229(2) . ? C8B N10B 1.390(3) . ? N10B C11B 1.423(3) . ? N10B C25B 1.479(3) . ? C11B C18B 1.389(3) . ? C11B C12B 1.396(3) . ? C12B C13B 1.382(3) . ? C13B C14B 1.411(3) . ? C14B O15B 1.368(3) . ? C14B C17B 1.389(3) . ? O15B C16B 1.442(3) . ? C17B C18B 1.391(3) . ? C18B C19B 1.507(3) . ? C19B O20B 1.416(2) . ? C19B C21B 1.524(3) . ? C19B C25B 1.585(3) . ? C21B C22B 1.501(3) . ? C22B O23B 1.209(3) . ? C22B O24B 1.364(3) . ? O24B C25B 1.469(2) . ? C25B C26B 1.503(3) . ? 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 C3A C2A C7A 121.4(2) . . ? C3A C2A Cl1A 119.15(18) . . ? C7A C2A Cl1A 119.43(18) . . ? C2A C3A C4A 119.0(2) . . ? C5A C4A C3A 120.6(2) . . ? C6A C5A C4A 118.9(2) . . ? C6A C5A C8A 117.01(19) . . ? C4A C5A C8A 123.6(2) . . ? C7A C6A C5A 120.8(2) . . ? C2A C7A C6A 119.3(2) . . ? O9A C8A N10A 120.3(2) . . ? O9A C8A C5A 119.29(19) . . ? N10A C8A C5A 120.40(19) . . ? C8A N10A C11A 122.17(18) . . ? C8A N10A C25A 128.73(19) . . ? C11A N10A C25A 109.05(16) . . ? C18A C11A C12A 120.4(2) . . ? C18A C11A N10A 110.17(19) . . ? C12A C11A N10A 129.30(19) . . ? C13A C12A C11A 118.2(2) . . ? C12A C13A C14A 121.5(2) . . ? O15A C14A C13A 114.9(2) . . ? O15A C14A C17A 125.1(2) . . ? C13A C14A C17A 119.9(2) . . ? C14A O15A C16A 117.0(2) . . ? C18A C17A C14A 118.4(2) . . ? C11A C18A C17A 121.5(2) . . ? C11A C18A C19A 110.44(19) . . ? C17A C18A C19A 128.05(19) . . ? O20A C19A C21A 109.51(17) . . ? O20A C19A C18A 113.13(17) . . ? C21A C19A C18A 114.12(19) . . ? O20A C19A C25A 114.43(18) . . ? C21A C19A C25A 102.95(16) . . ? C18A C19A C25A 102.19(16) . . ? C22A C21A C19A 104.42(17) . . ? O23A C22A O24A 120.9(2) . . ? O23A C22A C21A 129.3(2) . . ? O24A C22A C21A 109.73(17) . . ? C22A O24A C25A 112.05(16) . . ? O24A C25A N10A 107.39(16) . . ? O24A C25A C26A 109.72(17) . . ? N10A C25A C26A 116.41(18) . . ? O24A C25A C19A 103.60(16) . . ? N10A C25A C19A 104.63(17) . . ? C26A C25A C19A 114.12(18) . . ? C7B C2B C3B 121.3(2) . . ? C7B C2B Cl1B 120.15(18) . . ? C3B C2B Cl1B 118.51(18) . . ? C4B C3B C2B 119.3(2) . . ? C3B C4B C5B 120.1(2) . . ? C4B C5B C6B 119.2(2) . . ? C4B C5B C8B 122.58(19) . . ? C6B C5B C8B 117.94(19) . . ? C7B C6B C5B 121.0(2) . . ? C6B C7B C2B 119.0(2) . . ? O9B C8B N10B 120.3(2) . . ? O9B C8B C5B 120.3(2) . . ? N10B C8B C5B 119.26(18) . . ? C8B N10B C11B 122.86(18) . . ? C8B N10B C25B 128.35(18) . . ? C11B N10B C25B 108.29(16) . . ? C18B C11B C12B 120.8(2) . . ? C18B C11B N10B 111.17(18) . . ? C12B C11B N10B 127.9(2) . . ? C13B C12B C11B 117.1(2) . . ? C12B C13B C14B 122.2(2) . . ? O15B C14B C17B 124.3(2) . . ? O15B C14B C13B 115.3(2) . . ? C17B C14B C13B 120.3(2) . . ? C14B O15B C16B 117.90(19) . . ? C14B C17B C18B 117.2(2) . . ? C11B C18B C17B 122.38(19) . . ? C11B C18B C19B 110.65(18) . . ? C17B C18B C19B 126.95(19) . . ? O20B C19B C18B 112.37(16) . . ? O20B C19B C21B 109.28(17) . . ? C18B C19B C21B 114.47(17) . . ? O20B C19B C25B 114.98(17) . . ? C18B C19B C25B 101.47(16) . . ? C21B C19B C25B 103.93(15) . . ? C22B C21B C19B 103.80(17) . . ? O23B C22B O24B 120.5(2) . . ? O23B C22B C21B 128.7(2) . . ? O24B C22B C21B 110.87(17) . . ? C22B O24B C25B 111.98(17) . . ? O24B C25B N10B 107.51(16) . . ? O24B C25B C26B 109.73(17) . . ? N10B C25B C26B 116.03(17) . . ? O24B C25B C19B 103.20(15) . . ? N10B C25B C19B 105.53(16) . . ? C26B C25B C19B 113.90(18) . . ? 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 C7A C2A C3A C4A 0.5(4) . . . . ? Cl1A C2A C3A C4A -178.25(19) . . . . ? C2A C3A C4A C5A -1.3(3) . . . . ? C3A C4A C5A C6A 1.9(3) . . . . ? C3A C4A C5A C8A 174.4(2) . . . . ? C4A C5A C6A C7A -1.6(3) . . . . ? C8A C5A C6A C7A -174.6(2) . . . . ? C3A C2A C7A C6A -0.2(4) . . . . ? Cl1A C2A C7A C6A 178.52(19) . . . . ? C5A C6A C7A C2A 0.7(4) . . . . ? C6A C5A C8A O9A 36.5(3) . . . . ? C4A C5A C8A O9A -136.1(2) . . . . ? C6A C5A C8A N10A -145.0(2) . . . . ? C4A C5A C8A N10A 42.3(3) . . . . ? O9A C8A N10A C11A 18.9(3) . . . . ? C5A C8A N10A C11A -159.55(18) . . . . ? O9A C8A N10A C25A -158.3(2) . . . . ? C5A C8A N10A C25A 23.2(3) . . . . ? C8A N10A C11A C18A -170.21(18) . . . . ? C25A N10A C11A C18A 7.5(2) . . . . ? C8A N10A C11A C12A 13.8(3) . . . . ? C25A N10A C11A C12A -168.5(2) . . . . ? C18A C11A C12A C13A -1.6(3) . . . . ? N10A C11A C12A C13A 174.04(19) . . . . ? C11A C12A C13A C14A 0.3(3) . . . . ? C12A C13A C14A O15A -178.1(2) . . . . ? C12A C13A C14A C17A 1.1(3) . . . . ? C13A C14A O15A C16A -178.1(2) . . . . ? C17A C14A O15A C16A 2.7(3) . . . . ? O15A C14A C17A C18A 177.92(19) . . . . ? C13A C14A C17A C18A -1.2(3) . . . . ? C12A C11A C18A C17A 1.4(3) . . . . ? N10A C11A C18A C17A -174.95(18) . . . . ? C12A C11A C18A C19A -178.28(18) . . . . ? N10A C11A C18A C19A 5.3(2) . . . . ? C14A C17A C18A C11A 0.0(3) . . . . ? C14A C17A C18A C19A 179.6(2) . . . . ? C11A C18A C19A O20A 108.7(2) . . . . ? C17A C18A C19A O20A -71.0(3) . . . . ? C11A C18A C19A C21A -125.20(19) . . . . ? C17A C18A C19A C21A 55.1(3) . . . . ? C11A C18A C19A C25A -14.8(2) . . . . ? C17A C18A C19A C25A 165.5(2) . . . . ? O20A C19A C21A C22A -148.13(18) . . . . ? C18A C19A C21A C22A 83.9(2) . . . . ? C25A C19A C21A C22A -26.0(2) . . . . ? C19A C21A C22A O23A -162.4(2) . . . . ? C19A C21A C22A O24A 18.9(3) . . . . ? O23A C22A O24A C25A 178.5(2) . . . . ? C21A C22A O24A C25A -2.6(3) . . . . ? C22A O24A C25A N10A -124.51(19) . . . . ? C22A O24A C25A C26A 108.1(2) . . . . ? C22A O24A C25A C19A -14.1(2) . . . . ? C8A N10A C25A O24A -89.2(2) . . . . ? C11A N10A C25A O24A 93.27(18) . . . . ? C8A N10A C25A C26A 34.2(3) . . . . ? C11A N10A C25A C26A -143.34(19) . . . . ? C8A N10A C25A C19A 161.12(19) . . . . ? C11A N10A C25A C19A -16.4(2) . . . . ? O20A C19A C25A O24A 143.28(17) . . . . ? C21A C19A C25A O24A 24.5(2) . . . . ? C18A C19A C25A O24A -94.07(18) . . . . ? O20A C19A C25A N10A -104.33(19) . . . . ? C21A C19A C25A N10A 136.92(17) . . . . ? C18A C19A C25A N10A 18.32(19) . . . . ? O20A C19A C25A C26A 24.0(2) . . . . ? C21A C19A C25A C26A -94.7(2) . . . . ? C18A C19A C25A C26A 146.68(18) . . . . ? C7B C2B C3B C4B -0.4(4) . . . . ? Cl1B C2B C3B C4B 179.13(19) . . . . ? C2B C3B C4B C5B 1.3(4) . . . . ? C3B C4B C5B C6B -2.0(3) . . . . ? C3B C4B C5B C8B -176.2(2) . . . . ? C4B C5B C6B C7B 1.8(4) . . . . ? C8B C5B C6B C7B 176.4(2) . . . . ? C5B C6B C7B C2B -1.0(4) . . . . ? C3B C2B C7B C6B 0.3(4) . . . . ? Cl1B C2B C7B C6B -179.3(2) . . . . ? C4B C5B C8B O9B 134.9(2) . . . . ? C6B C5B C8B O9B -39.5(3) . . . . ? C4B C5B C8B N10B -42.2(3) . . . . ? C6B C5B C8B N10B 143.5(2) . . . . ? O9B C8B N10B C11B -17.7(3) . . . . ? C5B C8B N10B C11B 159.38(18) . . . . ? O9B C8B N10B C25B 153.1(2) . . . . ? C5B C8B N10B C25B -29.8(3) . . . . ? C8B N10B C11B C18B 167.09(18) . . . . ? C25B N10B C11B C18B -5.4(2) . . . . ? C8B N10B C11B C12B -16.6(3) . . . . ? C25B N10B C11B C12B 170.9(2) . . . . ? C18B C11B C12B C13B 1.2(3) . . . . ? N10B C11B C12B C13B -174.8(2) . . . . ? C11B C12B C13B C14B -0.3(3) . . . . ? C12B C13B C14B O15B 179.42(19) . . . . ? C12B C13B C14B C17B -0.6(3) . . . . ? C17B C14B O15B C16B 0.3(3) . . . . ? C13B C14B O15B C16B -179.7(2) . . . . ? O15B C14B C17B C18B -179.48(19) . . . . ? C13B C14B C17B C18B 0.5(3) . . . . ? C12B C11B C18B C17B -1.3(3) . . . . ? N10B C11B C18B C17B 175.27(18) . . . . ? C12B C11B C18B C19B 177.05(18) . . . . ? N10B C11B C18B C19B -6.3(2) . . . . ? C14B C17B C18B C11B 0.4(3) . . . . ? C14B C17B C18B C19B -177.68(19) . . . . ? C11B C18B C19B O20B -109.1(2) . . . . ? C17B C18B C19B O20B 69.1(3) . . . . ? C11B C18B C19B C21B 125.43(19) . . . . ? C17B C18B C19B C21B -56.3(3) . . . . ? C11B C18B C19B C25B 14.2(2) . . . . ? C17B C18B C19B C25B -167.52(19) . . . . ? O20B C19B C21B C22B 147.21(18) . . . . ? C18B C19B C21B C22B -85.8(2) . . . . ? C25B C19B C21B C22B 24.0(2) . . . . ? C19B C21B C22B O23B 164.2(2) . . . . ? C19B C21B C22B O24B -17.2(2) . . . . ? O23B C22B O24B C25B -179.24(19) . . . . ? C21B C22B O24B C25B 2.0(2) . . . . ? C22B O24B C25B N10B 124.69(18) . . . . ? C22B O24B C25B C26B -108.3(2) . . . . ? C22B O24B C25B C19B 13.4(2) . . . . ? C8B N10B C25B O24B 92.5(2) . . . . ? C11B N10B C25B O24B -95.63(18) . . . . ? C8B N10B C25B C26B -30.8(3) . . . . ? C11B N10B C25B C26B 141.14(19) . . . . ? C8B N10B C25B C19B -157.90(19) . . . . ? C11B N10B C25B C19B 14.0(2) . . . . ? O20B C19B C25B O24B -142.42(16) . . . . ? C18B C19B C25B O24B 96.05(16) . . . . ? C21B C19B C25B O24B -23.0(2) . . . . ? O20B C19B C25B N10B 104.89(18) . . . . ? C18B C19B C25B N10B -16.64(19) . . . . ? C21B C19B C25B N10B -135.72(16) . . . . ? O20B C19B C25B C26B -23.5(2) . . . . ? C18B C19B C25B C26B -145.05(17) . . . . ? C21B C19B C25B C26B 95.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.370 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.067 data_formII _database_code_depnum_ccdc_archive 'CCDC 892947' #TrackingRef 'form2abscor.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 Cl N O5' _chemical_formula_weight 373.78 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' Cl Cl 0.1484 0.1585 '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 8.6273(17) _cell_length_b 9.5152(19) _cell_length_c 10.644(2) _cell_angle_alpha 81.61(3) _cell_angle_beta 75.88(3) _cell_angle_gamma 86.06(3) _cell_volume 837.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9450 _exptl_absorpt_correction_T_max 0.9547 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20045 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.64 _reflns_number_total 3166 _reflns_number_gt 2781 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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. ; _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^)+(0.0319P)^2^+0.4263P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3166 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Cl1 Cl 0.26934(6) 0.57338(5) 0.04388(4) 0.04341(15) Uani 1 1 d . . . C2 C 0.22591(17) 0.63836(16) -0.10543(15) 0.0276(3) Uani 1 1 d . . . C3 C 0.17492(18) 0.54605(16) -0.17548(16) 0.0298(3) Uani 1 1 d . . . H3 H 0.1674 0.4475 -0.1437 0.036 Uiso 1 1 calc R . . C4 C 0.13504(17) 0.59899(15) -0.29227(16) 0.0274(3) Uani 1 1 d . . . H4 H 0.0990 0.5367 -0.3404 0.033 Uiso 1 1 calc R . . C5 C 0.14766(16) 0.74359(15) -0.33935(14) 0.0238(3) Uani 1 1 d . . . C6 C 0.20567(16) 0.83310(15) -0.27027(15) 0.0246(3) Uani 1 1 d . . . H6 H 0.2198 0.9305 -0.3045 0.030 Uiso 1 1 calc R . . C7 C 0.24295(17) 0.78183(16) -0.15231(15) 0.0270(3) Uani 1 1 d . . . H7 H 0.2796 0.8438 -0.1042 0.032 Uiso 1 1 calc R . . C8 C 0.10192(16) 0.80832(14) -0.46222(14) 0.0229(3) Uani 1 1 d . . . O9 O 0.18840(12) 0.89129(11) -0.54424(10) 0.0291(2) Uani 1 1 d . . . N10 N -0.04156(13) 0.77015(12) -0.48054(11) 0.0219(3) Uani 1 1 d . . . C11 C -0.08468(17) 0.79816(14) -0.60320(14) 0.0220(3) Uani 1 1 d . . . C12 C 0.01380(18) 0.81973(16) -0.72927(15) 0.0276(3) Uani 1 1 d . . . H12 H 0.1267 0.8221 -0.7430 0.033 Uiso 1 1 calc R . . C13 C -0.05863(19) 0.83764(16) -0.83352(15) 0.0301(3) Uani 1 1 d . . . H13 H 0.0061 0.8543 -0.9200 0.036 Uiso 1 1 calc R . . C14 C -0.22435(19) 0.83188(15) -0.81503(15) 0.0276(3) Uani 1 1 d . . . O15 O -0.28064(14) 0.85125(13) -0.92663(11) 0.0396(3) Uani 1 1 d . . . C16 C -0.4468(2) 0.8300(3) -0.90939(19) 0.0539(5) Uani 1 1 d . . . H16B H -0.4717 0.7332 -0.8664 0.081 Uiso 1 1 calc R . . H16A H -0.4735 0.8436 -0.9948 0.081 Uiso 1 1 calc R . . H16C H -0.5093 0.8985 -0.8551 0.081 Uiso 1 1 calc R . . C17 C -0.32170(18) 0.80808(15) -0.68952(14) 0.0253(3) Uani 1 1 d . . . H17 H -0.4343 0.8026 -0.6754 0.030 Uiso 1 1 calc R . . C18 C -0.24862(16) 0.79269(14) -0.58560(14) 0.0220(3) Uani 1 1 d . . . C19 C -0.32918(16) 0.77162(14) -0.44262(14) 0.0219(3) Uani 1 1 d . . . O20 O -0.41704(12) 0.89334(10) -0.39964(10) 0.0266(2) Uani 1 1 d . . . H20 H -0.3618 0.9654 -0.4292 0.032 Uiso 1 1 calc R . . C21 C -0.43472(17) 0.64368(15) -0.40007(15) 0.0250(3) Uani 1 1 d . . . H21B H -0.5180 0.6562 -0.3197 0.030 Uiso 1 1 calc R . . H21A H -0.4873 0.6286 -0.4697 0.030 Uiso 1 1 calc R . . C22 C -0.32205(17) 0.52158(15) -0.37522(14) 0.0252(3) Uani 1 1 d . . . O23 O -0.34169(14) 0.39648(11) -0.36501(12) 0.0356(3) Uani 1 1 d . . . O24 O -0.18357(12) 0.57025(10) -0.36098(10) 0.0256(2) Uani 1 1 d . . . C25 C -0.18440(16) 0.72587(14) -0.37821(14) 0.0222(3) Uani 1 1 d . . . C26 C -0.20590(18) 0.77758(16) -0.24717(14) 0.0277(3) Uani 1 1 d . . . H26A H -0.3165 0.7641 -0.1969 0.042 Uiso 1 1 calc R . . H26C H -0.1824 0.8787 -0.2605 0.042 Uiso 1 1 calc R . . H26B H -0.1328 0.7234 -0.1992 0.042 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 Cl1 0.0518(3) 0.0413(3) 0.0382(3) 0.00617(18) -0.0192(2) -0.00279(19) C2 0.0224(7) 0.0292(8) 0.0290(8) -0.0005(6) -0.0045(6) 0.0003(6) C3 0.0252(8) 0.0210(7) 0.0413(9) 0.0011(6) -0.0073(7) -0.0017(6) C4 0.0232(7) 0.0207(7) 0.0396(9) -0.0058(6) -0.0082(6) -0.0030(6) C5 0.0172(7) 0.0224(7) 0.0310(8) -0.0038(6) -0.0041(6) -0.0006(5) C6 0.0208(7) 0.0199(7) 0.0318(8) -0.0028(6) -0.0036(6) -0.0024(5) C7 0.0246(7) 0.0258(8) 0.0311(8) -0.0062(6) -0.0060(6) -0.0026(6) C8 0.0203(7) 0.0170(7) 0.0312(8) -0.0061(6) -0.0040(6) -0.0009(5) O9 0.0273(5) 0.0259(5) 0.0329(6) -0.0006(4) -0.0044(4) -0.0094(4) N10 0.0195(6) 0.0218(6) 0.0238(6) -0.0021(5) -0.0038(5) -0.0029(5) C11 0.0234(7) 0.0169(6) 0.0256(7) -0.0035(5) -0.0045(6) -0.0024(5) C12 0.0250(7) 0.0262(7) 0.0294(8) -0.0055(6) -0.0007(6) -0.0027(6) C13 0.0343(8) 0.0289(8) 0.0240(8) -0.0054(6) 0.0010(6) -0.0041(6) C14 0.0361(8) 0.0226(7) 0.0259(8) -0.0044(6) -0.0096(6) -0.0038(6) O15 0.0436(7) 0.0512(7) 0.0270(6) -0.0041(5) -0.0128(5) -0.0089(6) C16 0.0470(11) 0.0820(15) 0.0384(10) -0.0027(10) -0.0216(9) -0.0117(10) C17 0.0257(7) 0.0203(7) 0.0304(8) -0.0030(6) -0.0070(6) -0.0039(6) C18 0.0226(7) 0.0152(6) 0.0268(7) -0.0025(5) -0.0031(6) -0.0028(5) C19 0.0194(7) 0.0190(7) 0.0267(7) -0.0026(5) -0.0037(6) -0.0024(5) O20 0.0227(5) 0.0195(5) 0.0342(6) -0.0031(4) -0.0006(4) -0.0010(4) C21 0.0216(7) 0.0231(7) 0.0289(8) -0.0001(6) -0.0040(6) -0.0055(6) C22 0.0253(7) 0.0250(8) 0.0244(7) -0.0015(6) -0.0039(6) -0.0067(6) O23 0.0381(6) 0.0200(6) 0.0500(7) -0.0013(5) -0.0137(5) -0.0066(4) O24 0.0246(5) 0.0188(5) 0.0333(6) 0.0006(4) -0.0082(4) -0.0034(4) C25 0.0214(7) 0.0176(7) 0.0257(7) -0.0007(5) -0.0026(6) -0.0038(5) C26 0.0254(8) 0.0311(8) 0.0256(8) -0.0038(6) -0.0031(6) -0.0041(6) _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 Cl1 C2 1.7380(16) . ? C2 C3 1.388(2) . ? C2 C7 1.388(2) . ? C3 C4 1.386(2) . ? C4 C5 1.396(2) . ? C5 C6 1.392(2) . ? C5 C8 1.493(2) . ? C6 C7 1.384(2) . ? C8 O9 1.2265(18) . ? C8 N10 1.3793(18) . ? N10 C11 1.4269(19) . ? N10 C25 1.4714(18) . ? C11 C18 1.384(2) . ? C11 C12 1.397(2) . ? C12 C13 1.385(2) . ? C13 C14 1.399(2) . ? C14 O15 1.3734(19) . ? C14 C17 1.390(2) . ? O15 C16 1.424(2) . ? C17 C18 1.387(2) . ? C18 C19 1.501(2) . ? C19 O20 1.4106(17) . ? C19 C21 1.5187(19) . ? C19 C25 1.573(2) . ? C21 C22 1.498(2) . ? C22 O23 1.1993(18) . ? C22 O24 1.3601(18) . ? O24 C25 1.4650(16) . ? C25 C26 1.511(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 C3 C2 C7 121.26(14) . . ? C3 C2 Cl1 119.45(12) . . ? C7 C2 Cl1 119.29(12) . . ? C4 C3 C2 119.34(14) . . ? C3 C4 C5 120.19(14) . . ? C6 C5 C4 119.44(14) . . ? C6 C5 C8 117.62(13) . . ? C4 C5 C8 122.94(13) . . ? C7 C6 C5 120.77(13) . . ? C6 C7 C2 118.91(14) . . ? O9 C8 N10 121.10(14) . . ? O9 C8 C5 121.65(13) . . ? N10 C8 C5 117.24(12) . . ? C8 N10 C11 123.23(12) . . ? C8 N10 C25 126.83(12) . . ? C11 N10 C25 108.65(11) . . ? C18 C11 C12 120.07(14) . . ? C18 C11 N10 110.57(12) . . ? C12 C11 N10 129.23(13) . . ? C13 C12 C11 117.78(14) . . ? C12 C13 C14 121.83(14) . . ? O15 C14 C17 123.87(14) . . ? O15 C14 C13 115.93(13) . . ? C17 C14 C13 120.21(14) . . ? C14 O15 C16 116.17(13) . . ? C18 C17 C14 117.63(13) . . ? C11 C18 C17 122.46(13) . . ? C11 C18 C19 110.47(13) . . ? C17 C18 C19 127.07(13) . . ? O20 C19 C18 113.09(12) . . ? O20 C19 C21 109.41(11) . . ? C18 C19 C21 114.31(12) . . ? O20 C19 C25 114.36(11) . . ? C18 C19 C25 102.15(11) . . ? C21 C19 C25 103.04(11) . . ? C22 C21 C19 104.39(11) . . ? O23 C22 O24 120.75(14) . . ? O23 C22 C21 129.02(14) . . ? O24 C22 C21 110.21(12) . . ? C22 O24 C25 111.72(11) . . ? O24 C25 N10 107.28(11) . . ? O24 C25 C26 109.77(12) . . ? N10 C25 C26 117.54(12) . . ? O24 C25 C19 103.78(11) . . ? N10 C25 C19 104.86(11) . . ? C26 C25 C19 112.58(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.267 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.039