# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name R.E.Grigg _publ_contact_author_address ; Department of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_email R.Grigg@chemistry.leeds.ac.uk _publ_contact_author_phone '+44 (0)113 34 36501' loop_ _publ_author_name _publ_author_address R.E.Grigg ; Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; V.Sridharana ; Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; A.M.Derrick '' A.Keep '' C.Kilner '' 'Christian Lofberg' '' _publ_section_title ; Sequential One-Pot Bimetallic Ir(III) / Pd(0) Catalysed Mono- / Bis-Alkylation and Spirocyclisation Processes of 1,3-Dimethylbarbituric Acid and Allenes ; data_6b _database_code_depnum_ccdc_archive 'CCDC 622415' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 N2 O3' _chemical_formula_sum 'C22 H26 N2 O3' _chemical_formula_weight 366.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.0482(16) _cell_length_b 16.1047(16) _cell_length_c 32.609(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7902.7(15) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6524 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 22.33 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3136 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; graphite model mounted in "parallel" mode ; _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_radiation_detector 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 125890 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.99 _reflns_number_total 7760 _reflns_number_gt 5139 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution 'SHELXTL version 5.1(Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure solved in the orthorhombic space group Pbca with two molecules per asymmetric unit. Both molecules have the same numbering scheme and are distinguished with the suffixes A and B. Some hydrogen atoms could be located in the Fourier difference map but, in the final stages of the refinement, hydrogen atoms attached to carbon were placed in calculated positions and refined using a riding model. C-H distances: CH3, 0.98\A; CH2, 0.99\A; CH, 1.00\A; aromatic, 0.95\A; olefinic, 0.95\A. Methyl hydrogen atoms attached to C12B were disordered over two positions. C.Kilner 2 March 2006 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^)+(0.0403P)^2^+4.0377P] 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 SHELXL _refine_ls_extinction_coef 0.00020(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7760 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.004 _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 N12A N 0.16305(9) 0.06832(9) 0.70681(5) 0.0227(3) Uani 1 1 d . . . N14B N 0.17881(9) 0.15348(9) 0.29690(4) 0.0211(3) Uani 1 1 d . . . N14A N 0.31841(9) 0.09951(9) 0.69851(4) 0.0219(3) Uani 1 1 d . . . N12B N 0.33588(9) 0.18208(9) 0.29354(5) 0.0216(3) Uani 1 1 d . . . O13A O 0.22462(8) 0.18906(8) 0.73196(4) 0.0300(3) Uani 1 1 d . . . O13B O 0.27656(8) 0.06065(8) 0.26852(4) 0.0291(3) Uani 1 1 d . . . O11A O 0.10536(8) -0.05554(8) 0.68543(4) 0.0323(3) Uani 1 1 d . . . O11B O 0.39013(8) 0.30918(8) 0.31219(4) 0.0313(3) Uani 1 1 d . . . O15B O 0.08249(8) 0.25693(8) 0.31608(4) 0.0348(3) Uani 1 1 d . . . O15A O 0.41439(8) -0.00552(8) 0.68126(4) 0.0327(3) Uani 1 1 d . . . C15B C 0.15891(11) 0.23186(11) 0.31401(6) 0.0217(4) Uani 1 1 d . . . C13A C 0.23461(11) 0.12303(11) 0.71357(5) 0.0216(4) Uani 1 1 d . . . C10B C 0.23776(11) 0.27970(11) 0.33226(5) 0.0207(4) Uani 1 1 d . . . C13B C 0.26449(11) 0.12785(11) 0.28545(5) 0.0209(4) Uani 1 1 d . . . C8A C 0.34233(11) -0.15540(11) 0.63420(6) 0.0247(4) Uani 1 1 d . . . C10A C 0.25872(11) -0.02971(11) 0.66629(5) 0.0210(4) Uani 1 1 d . . . C2A C 0.31972(11) -0.02514(11) 0.59210(6) 0.0234(4) Uani 1 1 d . . . C15A C 0.33796(11) 0.01979(11) 0.68283(6) 0.0220(4) Uani 1 1 d . . . C8B C 0.16995(11) 0.40867(11) 0.37010(6) 0.0250(4) Uani 1 1 d . . . C1B C 0.25340(11) 0.24742(11) 0.37787(5) 0.0226(4) Uani 1 1 d . . . H1B1 H 0.2605 0.1863 0.3775 0.027 Uiso 1 1 calc R . . H1B2 H 0.3090 0.2718 0.3887 0.027 Uiso 1 1 calc R . . C1A C 0.24140(11) -0.00434(12) 0.61980(5) 0.0239(4) Uani 1 1 d . . . H1A1 H 0.1879 -0.0337 0.6097 0.029 Uiso 1 1 calc R . . H1A2 H 0.2295 0.0561 0.6183 0.029 Uiso 1 1 calc R . . C3A C 0.35750(11) -0.11093(11) 0.59726(6) 0.0229(4) Uani 1 1 d . . . C3B C 0.15460(11) 0.36099(11) 0.40574(6) 0.0233(4) Uani 1 1 d . . . C12B C 0.42566(11) 0.15570(12) 0.27886(6) 0.0303(5) Uani 1 1 d . . . H12A H 0.4220 0.0995 0.2675 0.045 Uiso 0.50 1 calc PR . . H12B H 0.4675 0.1562 0.3019 0.045 Uiso 0.50 1 calc PR . . H12C H 0.4463 0.1941 0.2576 0.045 Uiso 0.50 1 calc PR . . H12D H 0.4685 0.2004 0.2838 0.045 Uiso 0.50 1 calc PR . . H12E H 0.4230 0.1437 0.2494 0.045 Uiso 0.50 1 calc PR . . H12F H 0.4443 0.1057 0.2937 0.045 Uiso 0.50 1 calc PR . . C21B C 0.12974(12) 0.21512(11) 0.42847(6) 0.0288(4) Uani 1 1 d . . . H21B H 0.0828 0.2376 0.4445 0.035 Uiso 1 1 calc R . . C14B C 0.10439(12) 0.09726(12) 0.28507(6) 0.0301(5) Uani 1 1 d . . . H14A H 0.0497 0.1151 0.2988 0.045 Uiso 1 1 calc R . . H14B H 0.1186 0.0403 0.2933 0.045 Uiso 1 1 calc R . . H14C H 0.0959 0.0994 0.2553 0.045 Uiso 1 1 calc R . . C11B C 0.32689(11) 0.26118(11) 0.31087(5) 0.0216(4) Uani 1 1 d . . . C2B C 0.17657(11) 0.27027(11) 0.40611(6) 0.0238(4) Uani 1 1 d . . . C14A C 0.39417(12) 0.15699(12) 0.70696(6) 0.0291(4) Uani 1 1 d . . . H14D H 0.4102 0.1537 0.7360 0.044 Uiso 1 1 calc R . . H14E H 0.3766 0.2140 0.7002 0.044 Uiso 1 1 calc R . . H14F H 0.4454 0.1410 0.6901 0.044 Uiso 1 1 calc R . . C11A C 0.17016(11) -0.00939(11) 0.68772(6) 0.0225(4) Uani 1 1 d . . . C22B C 0.14225(13) 0.12166(12) 0.43145(6) 0.0327(5) Uani 1 1 d . . . H22B H 0.2065 0.1089 0.4268 0.039 Uiso 1 1 calc R . . C21A C 0.35465(12) 0.03054(11) 0.56551(6) 0.0282(4) Uani 1 1 d . . . H21A H 0.4015 0.0108 0.5486 0.034 Uiso 1 1 calc R . . C9B C 0.21826(13) 0.37442(11) 0.33223(6) 0.0278(4) Uani 1 1 d . . . H9B1 H 0.2754 0.4043 0.3294 0.033 Uiso 1 1 calc R . . H9B2 H 0.1821 0.3875 0.3077 0.033 Uiso 1 1 calc R . . C12A C 0.07524(12) 0.08977(12) 0.72536(6) 0.0318(5) Uani 1 1 d . . . H12H H 0.0293 0.0887 0.7041 0.048 Uiso 1 1 calc R . . H12G H 0.0782 0.1454 0.7374 0.048 Uiso 1 1 calc R . . H12I H 0.0606 0.0493 0.7468 0.048 Uiso 1 1 calc R . . C9A C 0.27927(12) -0.12412(11) 0.66782(6) 0.0255(4) Uani 1 1 d . . . H9A1 H 0.3057 -0.1373 0.6949 0.031 Uiso 1 1 calc R . . H9A2 H 0.2226 -0.1550 0.6657 0.031 Uiso 1 1 calc R . . C23A C 0.38056(14) 0.17678(12) 0.58963(6) 0.0335(5) Uani 1 1 d . . . H23A H 0.3684 0.1590 0.6182 0.040 Uiso 1 1 calc R . . H23B H 0.4451 0.1706 0.5845 0.040 Uiso 1 1 calc R . . C4A C 0.40900(12) -0.14934(12) 0.56607(6) 0.0297(4) Uani 1 1 d . . . H4A H 0.4175 -0.1211 0.5408 0.036 Uiso 1 1 calc R . . C4B C 0.11856(12) 0.40076(12) 0.44103(6) 0.0314(5) Uani 1 1 d . . . H4B H 0.1108 0.3699 0.4656 0.038 Uiso 1 1 calc R . . C7A C 0.38341(13) -0.23338(12) 0.63973(7) 0.0331(5) Uani 1 1 d . . . H7A H 0.3755 -0.2621 0.6649 0.040 Uiso 1 1 calc R . . C22A C 0.32812(12) 0.12055(11) 0.55948(6) 0.0284(4) Uani 1 1 d . . . H22A H 0.2634 0.1260 0.5658 0.034 Uiso 1 1 calc R . . C5B C 0.09450(13) 0.48429(13) 0.44004(7) 0.0381(5) Uani 1 1 d . . . H5B H 0.0709 0.5100 0.4639 0.046 Uiso 1 1 calc R . . C6A C 0.43557(14) -0.26942(12) 0.60896(7) 0.0398(5) Uani 1 1 d . . . H6A H 0.4628 -0.3219 0.6133 0.048 Uiso 1 1 calc R . . C27A C 0.34366(13) 0.15059(12) 0.51475(6) 0.0329(5) Uani 1 1 d . . . H27A H 0.4075 0.1456 0.5078 0.039 Uiso 1 1 calc R . . H27B H 0.3097 0.1150 0.4956 0.039 Uiso 1 1 calc R . . C23B C 0.08727(16) 0.07566(13) 0.39857(7) 0.0438(6) Uani 1 1 d . . . H23C H 0.1057 0.0949 0.3710 0.053 Uiso 1 1 calc R . . H23D H 0.0236 0.0894 0.4021 0.053 Uiso 1 1 calc R . . C5A C 0.44743(14) -0.22740(12) 0.57155(7) 0.0368(5) Uani 1 1 d . . . H5A H 0.4813 -0.2520 0.5502 0.044 Uiso 1 1 calc R . . C27B C 0.11595(13) 0.08913(12) 0.47454(7) 0.0357(5) Uani 1 1 d . . . H27C H 0.1531 0.1168 0.4956 0.043 Uiso 1 1 calc R . . H27D H 0.0531 0.1034 0.4801 0.043 Uiso 1 1 calc R . . C7B C 0.14294(13) 0.49246(12) 0.36944(7) 0.0344(5) Uani 1 1 d . . . H7B H 0.1505 0.5239 0.3451 0.041 Uiso 1 1 calc R . . C24A C 0.35402(15) 0.26844(12) 0.58444(7) 0.0426(6) Uani 1 1 d . . . H24A H 0.2916 0.2757 0.5933 0.051 Uiso 1 1 calc R . . H24B H 0.3919 0.3031 0.6024 0.051 Uiso 1 1 calc R . . C26A C 0.31398(14) 0.24183(13) 0.50973(7) 0.0418(6) Uani 1 1 d . . . H26A H 0.3260 0.2603 0.4813 0.050 Uiso 1 1 calc R . . H26B H 0.2492 0.2460 0.5146 0.050 Uiso 1 1 calc R . . C6B C 0.10514(13) 0.53033(13) 0.40397(7) 0.0399(6) Uani 1 1 d . . . H6B H 0.0869 0.5868 0.4029 0.048 Uiso 1 1 calc R . . C25A C 0.36342(15) 0.29866(13) 0.54001(8) 0.0450(6) Uani 1 1 d . . . H25A H 0.4272 0.3005 0.5326 0.054 Uiso 1 1 calc R . . H25B H 0.3395 0.3557 0.5378 0.054 Uiso 1 1 calc R . . C24B C 0.09959(18) -0.01956(13) 0.40136(8) 0.0540(7) Uani 1 1 d . . . H24C H 0.0616 -0.0469 0.3806 0.065 Uiso 1 1 calc R . . H24D H 0.1622 -0.0338 0.3952 0.065 Uiso 1 1 calc R . . C25B C 0.07526(16) -0.05225(13) 0.44417(8) 0.0502(6) Uani 1 1 d . . . H25C H 0.0885 -0.1124 0.4457 0.060 Uiso 1 1 calc R . . H25D H 0.0108 -0.0447 0.4489 0.060 Uiso 1 1 calc R . . C26B C 0.12820(15) -0.00576(13) 0.47778(8) 0.0491(6) Uani 1 1 d . . . H26C H 0.1080 -0.0247 0.5051 0.059 Uiso 1 1 calc R . . H26D H 0.1921 -0.0194 0.4751 0.059 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 N12A 0.0183(7) 0.0245(8) 0.0253(9) 0.0041(7) 0.0028(7) 0.0030(6) N14B 0.0173(7) 0.0228(8) 0.0233(8) 0.0006(7) -0.0017(6) -0.0007(6) N14A 0.0189(7) 0.0234(8) 0.0234(9) -0.0017(7) 0.0014(6) -0.0007(6) N12B 0.0153(7) 0.0231(8) 0.0264(9) -0.0008(7) 0.0023(6) 0.0002(6) O13A 0.0321(7) 0.0259(7) 0.0321(8) -0.0037(6) 0.0017(6) 0.0040(6) O13B 0.0316(7) 0.0224(7) 0.0333(8) -0.0051(6) 0.0020(6) 0.0014(5) O11A 0.0252(7) 0.0367(8) 0.0350(8) -0.0005(6) 0.0029(6) -0.0098(6) O11B 0.0277(7) 0.0325(8) 0.0337(8) -0.0046(6) 0.0057(6) -0.0111(6) O15B 0.0226(7) 0.0374(8) 0.0442(9) -0.0012(7) 0.0003(6) 0.0077(6) O15A 0.0199(7) 0.0342(8) 0.0438(9) -0.0055(6) 0.0006(6) 0.0038(5) C15B 0.0200(9) 0.0242(10) 0.0210(10) 0.0036(8) 0.0025(8) 0.0032(7) C13A 0.0237(9) 0.0236(10) 0.0175(10) 0.0055(8) -0.0009(8) 0.0031(7) C10B 0.0231(9) 0.0204(9) 0.0186(10) 0.0032(8) 0.0036(8) 0.0005(7) C13B 0.0222(9) 0.0211(10) 0.0193(10) 0.0035(8) -0.0011(8) 0.0012(7) C8A 0.0254(9) 0.0204(9) 0.0282(11) -0.0009(8) -0.0019(8) -0.0026(7) C10A 0.0211(9) 0.0209(9) 0.0209(10) 0.0009(8) 0.0003(8) -0.0011(7) C2A 0.0243(9) 0.0237(10) 0.0223(10) 0.0008(8) -0.0013(8) 0.0005(7) C15A 0.0213(9) 0.0242(10) 0.0207(10) 0.0028(8) 0.0020(8) 0.0010(7) C8B 0.0242(9) 0.0213(9) 0.0294(11) -0.0004(8) 0.0044(8) -0.0020(7) C1B 0.0239(8) 0.0204(9) 0.0235(10) 0.0025(8) 0.0008(8) -0.0009(7) C1A 0.0239(9) 0.0245(10) 0.0233(10) 0.0037(8) -0.0001(8) 0.0014(7) C3A 0.0227(9) 0.0205(9) 0.0256(11) -0.0005(8) -0.0013(8) -0.0023(7) C3B 0.0216(9) 0.0233(10) 0.0249(10) -0.0033(8) 0.0033(8) -0.0035(7) C12B 0.0187(9) 0.0336(11) 0.0387(12) -0.0047(9) 0.0054(8) 0.0017(8) C21B 0.0299(10) 0.0284(10) 0.0282(11) 0.0025(9) 0.0094(9) 0.0027(8) C14B 0.0222(9) 0.0355(11) 0.0325(12) -0.0021(9) -0.0040(9) -0.0071(8) C11B 0.0234(9) 0.0242(10) 0.0173(10) 0.0021(8) -0.0001(8) -0.0013(7) C2B 0.0247(9) 0.0252(10) 0.0214(10) 0.0015(8) 0.0003(8) -0.0007(7) C14A 0.0234(9) 0.0318(11) 0.0322(12) -0.0048(9) -0.0031(9) -0.0046(8) C11A 0.0215(9) 0.0259(10) 0.0200(10) 0.0051(8) -0.0011(8) -0.0015(7) C22B 0.0321(10) 0.0282(11) 0.0379(13) 0.0103(9) 0.0125(9) 0.0020(8) C21A 0.0291(10) 0.0257(10) 0.0297(11) 0.0023(9) 0.0066(9) 0.0027(8) C9B 0.0364(10) 0.0193(9) 0.0277(11) 0.0034(8) 0.0061(9) 0.0010(8) C12A 0.0208(9) 0.0361(11) 0.0387(12) 0.0025(10) 0.0073(9) 0.0049(8) C9A 0.0303(10) 0.0227(10) 0.0235(10) 0.0039(8) 0.0007(8) -0.0001(8) C23A 0.0416(12) 0.0302(11) 0.0287(11) 0.0042(9) 0.0050(10) 0.0008(9) C4A 0.0343(10) 0.0268(10) 0.0281(11) 0.0000(9) 0.0022(9) -0.0017(8) C4B 0.0300(10) 0.0336(11) 0.0306(12) -0.0056(9) 0.0077(9) -0.0064(8) C7A 0.0386(11) 0.0256(11) 0.0351(12) 0.0062(9) 0.0020(10) 0.0026(8) C22A 0.0288(10) 0.0235(10) 0.0330(11) 0.0067(9) 0.0061(9) 0.0027(8) C5B 0.0310(10) 0.0355(12) 0.0478(14) -0.0171(11) 0.0160(10) -0.0073(9) C6A 0.0452(12) 0.0237(11) 0.0506(14) 0.0022(10) 0.0050(11) 0.0104(9) C27A 0.0356(11) 0.0335(11) 0.0296(12) 0.0060(9) 0.0037(9) 0.0023(9) C23B 0.0652(15) 0.0327(12) 0.0334(13) 0.0058(10) 0.0085(11) -0.0055(11) C5A 0.0408(12) 0.0291(11) 0.0405(13) -0.0074(10) 0.0072(10) 0.0059(9) C27B 0.0329(11) 0.0357(12) 0.0385(13) 0.0142(10) 0.0031(9) 0.0006(9) C7B 0.0339(10) 0.0226(10) 0.0467(14) 0.0023(9) 0.0106(10) 0.0004(8) C24A 0.0455(13) 0.0274(11) 0.0549(15) -0.0027(10) 0.0073(11) 0.0022(9) C26A 0.0407(12) 0.0389(13) 0.0457(14) 0.0220(11) -0.0002(11) 0.0012(10) C6B 0.0352(11) 0.0218(10) 0.0627(16) -0.0070(11) 0.0158(11) -0.0005(8) C25A 0.0452(13) 0.0249(11) 0.0648(17) 0.0168(11) 0.0016(12) 0.0013(9) C24B 0.0711(17) 0.0305(13) 0.0604(17) -0.0013(12) 0.0218(14) -0.0081(11) C25B 0.0530(14) 0.0275(12) 0.0700(18) 0.0147(12) 0.0176(13) -0.0005(10) C26B 0.0461(13) 0.0391(13) 0.0622(17) 0.0253(12) 0.0109(12) 0.0061(10) _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 N12A C11A 1.402(2) . ? N12A C13A 1.409(2) . ? N12A C12A 1.494(2) . ? N14B C13B 1.404(2) . ? N14B C15B 1.412(2) . ? N14B C14B 1.491(2) . ? N14A C13A 1.405(2) . ? N14A C15A 1.413(2) . ? N14A C14A 1.494(2) . ? N12B C11B 1.400(2) . ? N12B C13B 1.409(2) . ? N12B C12B 1.495(2) . ? O13A C13A 1.230(2) . ? O13B C13B 1.228(2) . ? O11A C11A 1.228(2) . ? O11B C11B 1.227(2) . ? O15B C15B 1.221(2) . ? O15A C15A 1.221(2) . ? C15B C10B 1.535(2) . ? C10B C11B 1.541(2) . ? C10B C9B 1.554(2) . ? C10B C1B 1.593(2) . ? C8A C7A 1.411(3) . ? C8A C3A 1.420(3) . ? C8A C9A 1.535(3) . ? C10A C15A 1.532(2) . ? C10A C11A 1.540(2) . ? C10A C9A 1.552(2) . ? C10A C1A 1.592(2) . ? C2A C21A 1.354(3) . ? C2A C3A 1.503(2) . ? C2A C1A 1.522(2) . ? C8B C7B 1.409(3) . ? C8B C3B 1.412(3) . ? C8B C9B 1.535(3) . ? C1B C2B 1.523(2) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C3A C4A 1.421(3) . ? C3B C4B 1.424(3) . ? C3B C2B 1.498(2) . ? C12B H12A 0.9800 . ? C12B H12B 0.9800 . ? C12B H12C 0.9800 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C21B C2B 1.348(2) . ? C21B C22B 1.520(3) . ? C21B H21B 0.9500 . ? C14B H14A 0.9800 . ? C14B H14B 0.9800 . ? C14B H14C 0.9800 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C22B C23B 1.544(3) . ? C22B C27B 1.551(3) . ? C22B H22B 1.0000 . ? C21A C22A 1.516(2) . ? C21A H21A 0.9500 . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C12A H12H 0.9800 . ? C12A H12G 0.9800 . ? C12A H12I 0.9800 . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C23A C24A 1.538(3) . ? C23A C22A 1.552(3) . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? C4A C5A 1.395(3) . ? C4A H4A 0.9500 . ? C4B C5B 1.394(3) . ? C4B H4B 0.9500 . ? C7A C6A 1.400(3) . ? C7A H7A 0.9500 . ? C22A C27A 1.554(3) . ? C22A H22A 1.0000 . ? C5B C6B 1.400(3) . ? C5B H5B 0.9500 . ? C6A C5A 1.406(3) . ? C6A H6A 0.9500 . ? C27A C26A 1.544(3) . ? C27A H27A 0.9900 . ? C27A H27B 0.9900 . ? C23B C24B 1.547(3) . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? C5A H5A 0.9500 . ? C27B C26B 1.543(3) . ? C27B H27C 0.9900 . ? C27B H27D 0.9900 . ? C7B C6B 1.401(3) . ? C7B H7B 0.9500 . ? C24A C25A 1.535(3) . ? C24A H24A 0.9900 . ? C24A H24B 0.9900 . ? C26A C25A 1.538(3) . ? C26A H26A 0.9900 . ? C26A H26B 0.9900 . ? C6B H6B 0.9500 . ? C25A H25A 0.9900 . ? C25A H25B 0.9900 . ? C24B C25B 1.536(3) . ? C24B H24C 0.9900 . ? C24B H24D 0.9900 . ? C25B C26B 1.548(3) . ? C25B H25C 0.9900 . ? C25B H25D 0.9900 . ? C26B H26C 0.9900 . ? C26B H26D 0.9900 . ? 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 C11A N12A C13A 124.71(14) . . ? C11A N12A C12A 116.99(14) . . ? C13A N12A C12A 117.92(15) . . ? C13B N14B C15B 124.22(14) . . ? C13B N14B C14B 116.25(14) . . ? C15B N14B C14B 119.07(14) . . ? C13A N14A C15A 123.93(14) . . ? C13A N14A C14A 116.95(14) . . ? C15A N14A C14A 118.09(14) . . ? C11B N12B C13B 124.46(14) . . ? C11B N12B C12B 118.36(14) . . ? C13B N12B C12B 116.92(14) . . ? O15B C15B N14B 121.15(16) . . ? O15B C15B C10B 122.74(16) . . ? N14B C15B C10B 115.97(14) . . ? O13A C13A N14A 120.87(16) . . ? O13A C13A N12A 121.57(16) . . ? N14A C13A N12A 117.56(15) . . ? C15B C10B C11B 113.59(14) . . ? C15B C10B C9B 110.28(14) . . ? C11B C10B C9B 110.75(14) . . ? C15B C10B C1B 108.20(14) . . ? C11B C10B C1B 103.35(13) . . ? C9B C10B C1B 110.42(15) . . ? O13B C13B N14B 120.94(16) . . ? O13B C13B N12B 121.16(15) . . ? N14B C13B N12B 117.89(15) . . ? C7A C8A C3A 119.13(17) . . ? C7A C8A C9A 118.14(17) . . ? C3A C8A C9A 122.66(16) . . ? C15A C10A C11A 113.79(14) . . ? C15A C10A C9A 110.07(14) . . ? C11A C10A C9A 111.47(14) . . ? C15A C10A C1A 109.21(14) . . ? C11A C10A C1A 103.64(13) . . ? C9A C10A C1A 108.33(15) . . ? C21A C2A C3A 122.26(16) . . ? C21A C2A C1A 122.33(16) . . ? C3A C2A C1A 115.38(15) . . ? O15A C15A N14A 120.96(16) . . ? O15A C15A C10A 122.99(16) . . ? N14A C15A C10A 115.98(14) . . ? C7B C8B C3B 119.07(17) . . ? C7B C8B C9B 117.92(17) . . ? C3B C8B C9B 122.96(16) . . ? C2B C1B C10B 111.92(14) . . ? C2B C1B H1B1 109.2 . . ? C10B C1B H1B1 109.2 . . ? C2B C1B H1B2 109.2 . . ? C10B C1B H1B2 109.2 . . ? H1B1 C1B H1B2 107.9 . . ? C2A C1A C10A 112.45(14) . . ? C2A C1A H1A1 109.1 . . ? C10A C1A H1A1 109.1 . . ? C2A C1A H1A2 109.1 . . ? C10A C1A H1A2 109.1 . . ? H1A1 C1A H1A2 107.8 . . ? C8A C3A C4A 118.39(16) . . ? C8A C3A C2A 119.85(16) . . ? C4A C3A C2A 121.76(16) . . ? C8B C3B C4B 118.87(17) . . ? C8B C3B C2B 120.06(16) . . ? C4B C3B C2B 121.07(17) . . ? N12B C12B H12A 109.5 . . ? N12B C12B H12B 109.5 . . ? H12A C12B H12B 109.5 . . ? N12B C12B H12C 109.5 . . ? H12A C12B H12C 109.5 . . ? H12B C12B H12C 109.5 . . ? N12B C12B H12D 109.5 . . ? H12A C12B H12D 141.1 . . ? H12B C12B H12D 56.3 . . ? H12C C12B H12D 56.3 . . ? N12B C12B H12E 109.5 . . ? H12A C12B H12E 56.3 . . ? H12B C12B H12E 141.1 . . ? H12C C12B H12E 56.3 . . ? H12D C12B H12E 109.5 . . ? N12B C12B H12F 109.5 . . ? H12A C12B H12F 56.3 . . ? H12B C12B H12F 56.3 . . ? H12C C12B H12F 141.1 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C2B C21B C22B 128.48(17) . . ? C2B C21B H21B 115.8 . . ? C22B C21B H21B 115.8 . . ? N14B C14B H14A 109.5 . . ? N14B C14B H14B 109.5 . . ? H14A C14B H14B 109.5 . . ? N14B C14B H14C 109.5 . . ? H14A C14B H14C 109.5 . . ? H14B C14B H14C 109.5 . . ? O11B C11B N12B 120.84(16) . . ? O11B C11B C10B 122.50(16) . . ? N12B C11B C10B 116.29(14) . . ? C21B C2B C3B 122.12(16) . . ? C21B C2B C1B 124.37(16) . . ? C3B C2B C1B 113.47(15) . . ? N14A C14A H14D 109.5 . . ? N14A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? N14A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? O11A C11A N12A 120.43(16) . . ? O11A C11A C10A 122.07(16) . . ? N12A C11A C10A 117.21(14) . . ? C21B C22B C23B 111.38(17) . . ? C21B C22B C27B 111.15(16) . . ? C23B C22B C27B 109.29(16) . . ? C21B C22B H22B 108.3 . . ? C23B C22B H22B 108.3 . . ? C27B C22B H22B 108.3 . . ? C2A C21A C22A 127.90(17) . . ? C2A C21A H21A 116.1 . . ? C22A C21A H21A 116.1 . . ? C8B C9B C10B 116.21(15) . . ? C8B C9B H9B1 108.2 . . ? C10B C9B H9B1 108.2 . . ? C8B C9B H9B2 108.2 . . ? C10B C9B H9B2 108.2 . . ? H9B1 C9B H9B2 107.4 . . ? N12A C12A H12H 109.5 . . ? N12A C12A H12G 109.5 . . ? H12H C12A H12G 109.5 . . ? N12A C12A H12I 109.5 . . ? H12H C12A H12I 109.5 . . ? H12G C12A H12I 109.5 . . ? C8A C9A C10A 114.95(15) . . ? C8A C9A H9A1 108.5 . . ? C10A C9A H9A1 108.5 . . ? C8A C9A H9A2 108.5 . . ? C10A C9A H9A2 108.5 . . ? H9A1 C9A H9A2 107.5 . . ? C24A C23A C22A 110.98(17) . . ? C24A C23A H23A 109.4 . . ? C22A C23A H23A 109.4 . . ? C24A C23A H23B 109.4 . . ? C22A C23A H23B 109.4 . . ? H23A C23A H23B 108.0 . . ? C5A C4A C3A 121.78(18) . . ? C5A C4A H4A 119.1 . . ? C3A C4A H4A 119.1 . . ? C5B C4B C3B 120.96(19) . . ? C5B C4B H4B 119.5 . . ? C3B C4B H4B 119.5 . . ? C6A C7A C8A 121.53(19) . . ? C6A C7A H7A 119.2 . . ? C8A C7A H7A 119.2 . . ? C21A C22A C23A 109.98(16) . . ? C21A C22A C27A 112.31(16) . . ? C23A C22A C27A 109.65(16) . . ? C21A C22A H22A 108.3 . . ? C23A C22A H22A 108.3 . . ? C27A C22A H22A 108.3 . . ? C4B C5B C6B 120.07(19) . . ? C4B C5B H5B 120.0 . . ? C6B C5B H5B 120.0 . . ? C7A C6A C5A 119.56(19) . . ? C7A C6A H6A 120.2 . . ? C5A C6A H6A 120.2 . . ? C26A C27A C22A 110.61(17) . . ? C26A C27A H27A 109.5 . . ? C22A C27A H27A 109.5 . . ? C26A C27A H27B 109.5 . . ? C22A C27A H27B 109.5 . . ? H27A C27A H27B 108.1 . . ? C22B C23B C24B 111.75(19) . . ? C22B C23B H23C 109.3 . . ? C24B C23B H23C 109.3 . . ? C22B C23B H23D 109.3 . . ? C24B C23B H23D 109.3 . . ? H23C C23B H23D 107.9 . . ? C4A C5A C6A 119.48(19) . . ? C4A C5A H5A 120.3 . . ? C6A C5A H5A 120.3 . . ? C26B C27B C22B 111.47(18) . . ? C26B C27B H27C 109.3 . . ? C22B C27B H27C 109.3 . . ? C26B C27B H27D 109.3 . . ? C22B C27B H27D 109.3 . . ? H27C C27B H27D 108.0 . . ? C6B C7B C8B 121.4(2) . . ? C6B C7B H7B 119.3 . . ? C8B C7B H7B 119.3 . . ? C25A C24A C23A 112.60(18) . . ? C25A C24A H24A 109.1 . . ? C23A C24A H24A 109.1 . . ? C25A C24A H24B 109.1 . . ? C23A C24A H24B 109.1 . . ? H24A C24A H24B 107.8 . . ? C25A C26A C27A 110.99(17) . . ? C25A C26A H26A 109.4 . . ? C27A C26A H26A 109.4 . . ? C25A C26A H26B 109.4 . . ? C27A C26A H26B 109.4 . . ? H26A C26A H26B 108.0 . . ? C5B C6B C7B 119.42(19) . . ? C5B C6B H6B 120.3 . . ? C7B C6B H6B 120.3 . . ? C24A C25A C26A 111.87(17) . . ? C24A C25A H25A 109.2 . . ? C26A C25A H25A 109.2 . . ? C24A C25A H25B 109.2 . . ? C26A C25A H25B 109.2 . . ? H25A C25A H25B 107.9 . . ? C25B C24B C23B 111.38(19) . . ? C25B C24B H24C 109.4 . . ? C23B C24B H24C 109.4 . . ? C25B C24B H24D 109.4 . . ? C23B C24B H24D 109.4 . . ? H24C C24B H24D 108.0 . . ? C24B C25B C26B 110.79(19) . . ? C24B C25B H25C 109.5 . . ? C26B C25B H25C 109.5 . . ? C24B C25B H25D 109.5 . . ? C26B C25B H25D 109.5 . . ? H25C C25B H25D 108.1 . . ? C27B C26B C25B 111.66(19) . . ? C27B C26B H26C 109.3 . . ? C25B C26B H26C 109.3 . . ? C27B C26B H26D 109.3 . . ? C25B C26B H26D 109.3 . . ? H26C C26B H26D 107.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.261 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.041 data_8b _database_code_depnum_ccdc_archive 'CCDC 622416' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl2 N2 O5' _chemical_formula_sum 'C24 H24 Cl2 N2 O5' _chemical_formula_weight 491.35 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 monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.6087(2) _cell_length_b 8.62390(10) _cell_length_c 19.4116(2) _cell_angle_alpha 90.00 _cell_angle_beta 123.8230(10) _cell_angle_gamma 90.00 _cell_volume 2309.81(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 71120 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 86679 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4522 _reflns_number_gt 3999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2004)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Cryst. 1994, 27, 435-436. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III Version 1.08 (Farrugia, 2005) ; _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure solved in the monoclinic spacegroup P21/n and was transformed to the standard setting P21/c. All hydrogen atoms could be located in the Fourier difference map but, in the final stages of the refinement, they were placed in calculated positions and refined using a riding model. C-H distances: CH3, 0.98\A; CH2, 0.99\A; aromatic, 0.95\A, ethylinic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. There is a high positive residual electron density of 1.18 e \A\^3 located 2.04\A from Cl(25) and 1.18\A from Cl(26). C.Kilner 20 June 2006 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^)+(0.0890P)^2^+1.8606P] 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 4522 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1473 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.32047(15) 0.3478(2) -0.37124(13) 0.0302(4) Uani 1 1 d . . . C2 C -0.28213(15) 0.4466(2) -0.41163(13) 0.0308(4) Uani 1 1 d . . . C3 C -0.15460(19) 0.5160(3) -0.43118(17) 0.0464(6) Uani 1 1 d . . . H3A H -0.0916 0.4777 -0.4172 0.056 Uiso 1 1 calc R . . H3B H -0.1474 0.6224 -0.4107 0.056 Uiso 1 1 calc R . . H3C H -0.2009 0.5145 -0.4915 0.056 Uiso 1 1 calc R . . C4 C -0.12853(15) 0.3014(2) -0.33813(14) 0.0324(5) Uani 1 1 d . . . C5 C -0.10073(18) 0.0782(3) -0.25017(16) 0.0437(6) Uani 1 1 d . . . H5A H -0.1130 0.0599 -0.2070 0.052 Uiso 1 1 calc R . . H5B H -0.0331 0.1100 -0.2244 0.052 Uiso 1 1 calc R . . H5C H -0.1129 -0.0174 -0.2819 0.052 Uiso 1 1 calc R . . C6 C -0.25651(15) 0.2126(2) -0.32005(13) 0.0308(4) Uani 1 1 d . . . C10 C -0.41983(15) 0.2795(3) -0.44113(14) 0.0339(5) Uani 1 1 d . . . H10A H -0.4468 0.2161 -0.4160 0.041 Uiso 1 1 calc R . . H10B H -0.4656 0.3653 -0.4723 0.041 Uiso 1 1 calc R . . C11 C -0.41008(14) 0.1802(2) -0.50030(14) 0.0320(5) Uani 1 1 d . . . C13 C -0.40188(15) 0.1615(2) -0.62108(13) 0.0309(4) Uani 1 1 d . . . C14 C -0.38053(15) 0.0021(2) -0.60591(14) 0.0325(5) Uani 1 1 d . . . C20 C -0.33214(16) 0.4582(3) -0.31348(14) 0.0347(5) Uani 1 1 d . . . H20A H -0.3839 0.5346 -0.3480 0.042 Uiso 1 1 calc R . . H20B H -0.3525 0.3966 -0.2827 0.042 Uiso 1 1 calc R . . C21 C -0.23888(18) 0.5445(3) -0.25180(15) 0.0378(5) Uani 1 1 d . . . C22 C -0.2275(2) 0.6927(3) -0.26420(17) 0.0490(6) Uani 1 1 d . . . H22A H -0.1682 0.7443 -0.2265 0.059 Uiso 1 1 calc R . . H22B H -0.2788 0.7467 -0.3108 0.059 Uiso 1 1 calc R . . C23 C -0.15916(17) 0.4584(3) -0.17914(14) 0.0345(5) Uani 1 1 d . . . C25 C 0.01179(16) 0.4050(3) -0.08239(15) 0.0375(5) Uani 1 1 d . . . C26 C -0.00870(17) 0.2985(3) -0.04081(14) 0.0371(5) Uani 1 1 d . . . C31 C -0.40494(18) 0.3851(3) -0.69526(15) 0.0375(5) Uani 1 1 d . . . H31A H -0.3998 0.4130 -0.7416 0.045 Uiso 1 1 calc R . . H31B H -0.3492 0.4270 -0.6436 0.045 Uiso 1 1 calc R . . H31C H -0.4649 0.4283 -0.7047 0.045 Uiso 1 1 calc R . . C41 C -0.35357(18) -0.2364(3) -0.65147(17) 0.0436(6) Uani 1 1 d . . . H41A H -0.3461 -0.2778 -0.6946 0.052 Uiso 1 1 calc R . . H41B H -0.4106 -0.2832 -0.6569 0.052 Uiso 1 1 calc R . . H41C H -0.2957 -0.2610 -0.5968 0.052 Uiso 1 1 calc R . . C12 C -0.41695(14) 0.2483(2) -0.56929(13) 0.0310(4) Uani 1 1 d . . . H12 H -0.4321 0.3554 -0.5804 0.037 Uiso 1 1 calc R . . C15 C -0.37519(15) -0.0661(2) -0.53910(14) 0.0353(5) Uani 1 1 d . . . H15 H -0.3617 -0.1738 -0.5288 0.042 Uiso 1 1 calc R . . C16 C -0.38961(15) 0.0228(3) -0.48653(14) 0.0344(5) Uani 1 1 d . . . H16 H -0.3853 -0.0254 -0.4406 0.041 Uiso 1 1 calc R . . C24 C -0.06163(17) 0.4851(3) -0.15069(15) 0.0375(5) Uani 1 1 d . . . H24 H -0.0462 0.5580 -0.1783 0.045 Uiso 1 1 calc R . . C28 C -0.17855(17) 0.3511(3) -0.13669(14) 0.0381(5) Uani 1 1 d . . . H28 H -0.2438 0.3312 -0.1549 0.046 Uiso 1 1 calc R . . C27 C -0.10404(18) 0.2724(3) -0.06800(15) 0.0404(5) Uani 1 1 d . . . H27 H -0.1188 0.2002 -0.0396 0.048 Uiso 1 1 calc R . . N3 N -0.19028(13) 0.4161(2) -0.39229(11) 0.0324(4) Uani 1 1 d . . . N5 N -0.16557(13) 0.2015(2) -0.30620(11) 0.0316(4) Uani 1 1 d . . . O2 O -0.33001(12) 0.55165(18) -0.45849(10) 0.0378(4) Uani 1 1 d . . . O4 O -0.04649(12) 0.2883(2) -0.32021(12) 0.0445(4) Uani 1 1 d . . . O6 O -0.28334(12) 0.11798(19) -0.29092(10) 0.0388(4) Uani 1 1 d . . . O30 O -0.40632(11) 0.21962(17) -0.68923(9) 0.0345(4) Uani 1 1 d . . . O40 O -0.36568(12) -0.07182(17) -0.66042(10) 0.0379(4) Uani 1 1 d . . . Cl25 Cl 0.13139(4) 0.44123(7) -0.05009(4) 0.0472(2) Uani 1 1 d . . . Cl26 Cl 0.08221(5) 0.19658(8) 0.04468(4) 0.0465(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0277(10) 0.0281(10) 0.0348(11) 0.0036(9) 0.0174(9) 0.0013(8) C2 0.0311(10) 0.0278(10) 0.0306(10) -0.0010(8) 0.0152(9) -0.0033(8) C3 0.0450(14) 0.0470(14) 0.0526(14) 0.0065(12) 0.0305(12) -0.0082(11) C4 0.0314(11) 0.0273(10) 0.0366(11) -0.0036(8) 0.0177(9) -0.0021(8) C5 0.0409(13) 0.0365(13) 0.0476(14) 0.0128(10) 0.0208(11) 0.0125(10) C6 0.0323(11) 0.0269(10) 0.0300(10) 0.0007(8) 0.0154(9) -0.0010(8) C10 0.0261(10) 0.0345(11) 0.0389(12) 0.0021(9) 0.0168(9) -0.0006(8) C11 0.0221(9) 0.0320(11) 0.0366(11) 0.0001(9) 0.0130(9) -0.0017(8) C13 0.0249(10) 0.0271(10) 0.0338(10) 0.0005(8) 0.0120(8) -0.0005(8) C14 0.0244(10) 0.0260(10) 0.0401(11) -0.0026(9) 0.0136(9) -0.0021(8) C20 0.0367(11) 0.0313(11) 0.0380(11) 0.0027(9) 0.0221(10) 0.0045(9) C21 0.0450(13) 0.0323(12) 0.0414(12) -0.0031(9) 0.0273(11) -0.0036(9) C22 0.0580(16) 0.0357(13) 0.0438(14) 0.0022(10) 0.0226(12) -0.0040(11) C23 0.0376(12) 0.0314(11) 0.0365(11) -0.0068(9) 0.0218(10) -0.0043(9) C25 0.0349(11) 0.0348(11) 0.0390(12) -0.0109(9) 0.0181(10) -0.0029(9) C26 0.0377(12) 0.0366(12) 0.0335(11) -0.0050(9) 0.0177(10) 0.0029(9) C31 0.0450(13) 0.0262(11) 0.0389(12) 0.0035(9) 0.0220(10) 0.0037(9) C41 0.0424(13) 0.0239(11) 0.0556(15) -0.0042(10) 0.0218(12) 0.0008(9) C12 0.0240(9) 0.0259(10) 0.0356(11) 0.0021(8) 0.0121(9) 0.0010(8) C15 0.0275(10) 0.0249(10) 0.0454(12) 0.0006(9) 0.0153(10) -0.0033(8) C16 0.0291(10) 0.0295(11) 0.0398(12) 0.0037(9) 0.0161(9) -0.0037(8) C24 0.0439(13) 0.0307(11) 0.0430(12) -0.0064(9) 0.0275(11) -0.0058(9) C28 0.0360(12) 0.0392(12) 0.0410(12) -0.0034(10) 0.0226(10) -0.0037(10) C27 0.0427(13) 0.0417(13) 0.0392(12) 0.0004(10) 0.0243(11) 0.0009(10) N3 0.0314(9) 0.0299(9) 0.0372(10) 0.0027(7) 0.0199(8) -0.0030(7) N5 0.0294(9) 0.0264(9) 0.0357(9) 0.0030(7) 0.0162(8) 0.0030(7) O2 0.0390(9) 0.0306(8) 0.0384(8) 0.0081(7) 0.0182(7) 0.0025(6) O4 0.0317(8) 0.0388(9) 0.0633(11) -0.0010(8) 0.0267(8) -0.0003(7) O6 0.0417(9) 0.0334(8) 0.0420(9) 0.0071(7) 0.0238(7) -0.0023(7) O30 0.0391(8) 0.0255(7) 0.0365(8) 0.0006(6) 0.0195(7) 0.0024(6) O40 0.0406(9) 0.0240(8) 0.0468(9) -0.0032(6) 0.0229(8) 0.0008(6) Cl25 0.0347(3) 0.0448(4) 0.0563(4) -0.0045(3) 0.0217(3) -0.0031(2) Cl26 0.0455(4) 0.0491(4) 0.0367(3) 0.0004(2) 0.0179(3) 0.0101(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 C1 C6 1.517(3) . ? C1 C2 1.517(3) . ? C1 C10 1.555(3) . ? C1 C20 1.563(3) . ? C2 O2 1.215(3) . ? C2 N3 1.378(3) . ? C3 N3 1.470(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 O4 1.210(3) . ? C4 N5 1.389(3) . ? C4 N3 1.391(3) . ? C5 N5 1.473(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 O6 1.210(3) . ? C6 N5 1.382(3) . ? C10 C11 1.512(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.388(3) . ? C11 C12 1.408(3) . ? C13 O30 1.378(3) . ? C13 C12 1.383(3) . ? C13 C14 1.410(3) . ? C14 O40 1.370(3) . ? C14 C15 1.381(3) . ? C20 C21 1.524(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.333(3) . ? C21 C23 1.488(3) . ? C22 H22A 0.9500 . ? C22 H22B 0.9500 . ? C23 C28 1.391(3) . ? C23 C24 1.409(3) . ? C25 C26 1.384(3) . ? C25 C24 1.386(3) . ? C25 Cl25 1.746(2) . ? C26 C27 1.381(3) . ? C26 Cl26 1.737(2) . ? C31 O30 1.433(3) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C41 O40 1.431(3) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C12 H12 0.9500 . ? C15 C16 1.400(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C24 H24 0.9500 . ? C28 C27 1.390(3) . ? C28 H28 0.9500 . ? C27 H27 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 C6 C1 C2 115.33(17) . . ? C6 C1 C10 107.23(17) . . ? C2 C1 C10 107.99(17) . . ? C6 C1 C20 108.63(17) . . ? C2 C1 C20 106.50(17) . . ? C10 C1 C20 111.20(17) . . ? O2 C2 N3 120.7(2) . . ? O2 C2 C1 121.17(19) . . ? N3 C2 C1 118.13(18) . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O4 C4 N5 121.4(2) . . ? O4 C4 N3 121.5(2) . . ? N5 C4 N3 117.07(18) . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O6 C6 N5 120.6(2) . . ? O6 C6 C1 121.26(19) . . ? N5 C6 C1 118.15(18) . . ? C11 C10 C1 111.54(17) . . ? C11 C10 H10A 109.3 . . ? C1 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C1 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C16 C11 C12 118.2(2) . . ? C16 C11 C10 121.7(2) . . ? C12 C11 C10 120.01(19) . . ? O30 C13 C12 124.52(19) . . ? O30 C13 C14 115.35(19) . . ? C12 C13 C14 120.1(2) . . ? O40 C14 C15 125.6(2) . . ? O40 C14 C13 115.1(2) . . ? C15 C14 C13 119.3(2) . . ? C21 C20 C1 112.54(18) . . ? C21 C20 H20A 109.1 . . ? C1 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? C1 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C23 120.6(2) . . ? C22 C21 C20 120.7(2) . . ? C23 C21 C20 118.7(2) . . ? C21 C22 H22A 120.0 . . ? C21 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? C28 C23 C24 118.1(2) . . ? C28 C23 C21 121.1(2) . . ? C24 C23 C21 120.8(2) . . ? C26 C25 C24 121.1(2) . . ? C26 C25 Cl25 120.60(19) . . ? C24 C25 Cl25 118.25(19) . . ? C27 C26 C25 119.2(2) . . ? C27 C26 Cl26 118.99(19) . . ? C25 C26 Cl26 121.85(18) . . ? O30 C31 H31A 109.5 . . ? O30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O40 C41 H41A 109.5 . . ? O40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C13 C12 C11 120.94(19) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C15 C16 120.2(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 121.2(2) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C25 C24 C23 120.0(2) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C27 C28 C23 121.1(2) . . ? C27 C28 H28 119.4 . . ? C23 C28 H28 119.4 . . ? C26 C27 C28 120.4(2) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C2 N3 C4 125.44(18) . . ? C2 N3 C3 116.74(19) . . ? C4 N3 C3 117.81(19) . . ? C6 N5 C4 125.28(18) . . ? C6 N5 C5 117.66(18) . . ? C4 N5 C5 117.00(18) . . ? C13 O30 C31 116.48(17) . . ? C14 O40 C41 116.19(19) . . ? 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 C6 C1 C2 O2 175.05(19) . . . . ? C10 C1 C2 O2 55.2(3) . . . . ? C20 C1 C2 O2 -64.4(2) . . . . ? C6 C1 C2 N3 -6.4(3) . . . . ? C10 C1 C2 N3 -126.2(2) . . . . ? C20 C1 C2 N3 114.2(2) . . . . ? C2 C1 C6 O6 -173.5(2) . . . . ? C10 C1 C6 O6 -53.1(3) . . . . ? C20 C1 C6 O6 67.1(3) . . . . ? C2 C1 C6 N5 7.6(3) . . . . ? C10 C1 C6 N5 127.9(2) . . . . ? C20 C1 C6 N5 -111.8(2) . . . . ? C6 C1 C10 C11 -64.8(2) . . . . ? C2 C1 C10 C11 60.1(2) . . . . ? C20 C1 C10 C11 176.59(17) . . . . ? C1 C10 C11 C16 88.7(2) . . . . ? C1 C10 C11 C12 -88.1(2) . . . . ? O30 C13 C14 O40 1.0(3) . . . . ? C12 C13 C14 O40 -179.14(18) . . . . ? O30 C13 C14 C15 -179.63(18) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C6 C1 C20 C21 70.2(2) . . . . ? C2 C1 C20 C21 -54.6(2) . . . . ? C10 C1 C20 C21 -172.05(18) . . . . ? C1 C20 C21 C22 102.5(3) . . . . ? C1 C20 C21 C23 -75.1(2) . . . . ? C22 C21 C23 C28 142.5(3) . . . . ? C20 C21 C23 C28 -39.9(3) . . . . ? C22 C21 C23 C24 -36.6(3) . . . . ? C20 C21 C23 C24 141.0(2) . . . . ? C24 C25 C26 C27 -0.2(3) . . . . ? Cl25 C25 C26 C27 -179.91(18) . . . . ? C24 C25 C26 Cl26 179.80(17) . . . . ? Cl25 C25 C26 Cl26 0.0(3) . . . . ? O30 C13 C12 C11 -179.35(19) . . . . ? C14 C13 C12 C11 0.8(3) . . . . ? C16 C11 C12 C13 -1.2(3) . . . . ? C10 C11 C12 C13 175.68(18) . . . . ? O40 C14 C15 C16 178.45(19) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C12 C11 C16 C15 0.6(3) . . . . ? C10 C11 C16 C15 -176.25(19) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C26 C25 C24 C23 -0.2(3) . . . . ? Cl25 C25 C24 C23 179.53(17) . . . . ? C28 C23 C24 C25 0.2(3) . . . . ? C21 C23 C24 C25 179.3(2) . . . . ? C24 C23 C28 C27 0.1(3) . . . . ? C21 C23 C28 C27 -178.9(2) . . . . ? C25 C26 C27 C28 0.5(3) . . . . ? Cl26 C26 C27 C28 -179.42(18) . . . . ? C23 C28 C27 C26 -0.5(4) . . . . ? O2 C2 N3 C4 178.5(2) . . . . ? C1 C2 N3 C4 -0.1(3) . . . . ? O2 C2 N3 C3 -0.2(3) . . . . ? C1 C2 N3 C3 -178.8(2) . . . . ? O4 C4 N3 C2 -175.2(2) . . . . ? N5 C4 N3 C2 5.5(3) . . . . ? O4 C4 N3 C3 3.5(3) . . . . ? N5 C4 N3 C3 -175.8(2) . . . . ? O6 C6 N5 C4 178.4(2) . . . . ? C1 C6 N5 C4 -2.6(3) . . . . ? O6 C6 N5 C5 -4.4(3) . . . . ? C1 C6 N5 C5 174.52(19) . . . . ? O4 C4 N5 C6 176.6(2) . . . . ? N3 C4 N5 C6 -4.0(3) . . . . ? O4 C4 N5 C5 -0.5(3) . . . . ? N3 C4 N5 C5 178.82(19) . . . . ? C12 C13 O30 C31 14.4(3) . . . . ? C14 C13 O30 C31 -165.73(19) . . . . ? C15 C14 O40 C41 6.8(3) . . . . ? C13 C14 O40 C41 -173.93(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.179 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.072