# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name "Paul O'Neill" _publ_contact_author_email P.M.ONEILL01@LIVERPOOL.AC.UK _publ_section_title ; Synthesis, In Vitro and In Vivo Antimalarial Assessment of Sulfide, Sulfone and Vinyl Amide Substituted 1,2,4-Trioxanes prepared via Thiol-Olefin Co-Oxygenation (TOCO) of Allylic Alcohols ; loop_ _publ_author_name "P O'Neill" 'Richard Amewu' 'John Bacsa' 'Jill Davies' 'Peter D. Gibbons' 'Charlotte Hall' ; A.E.Mercer ; 'Amira Mukhtar' 'Gemma Nixon' 'Karen Rimmer' 'Andrew Stachulski' 'Paul A. Stocks' 'Livia Vivas' ; S.A.Ward ; # Attachment 'rka1302m_compound35_DMF.cif' data_rka1302m _database_code_depnum_ccdc_archive 'CCDC 680267' #TrackingRef 'rka1302m_compound35_DMF.cif' _audit_update_record ; 2008-03-04 # Formatted by J.Bacsa ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common rka1302 _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 Cl O5 S, C3 H7 N O' _chemical_formula_sum 'C24 H30 Cl N O6 S' _chemical_formula_weight 496.00 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' Cl Cl 0.1484 0.1585 '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' S S 0.1246 0.1234 '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 5.6889(13) _cell_length_b 13.461(3) _cell_length_c 16.663(4) _cell_angle_alpha 67.393(4) _cell_angle_beta 80.926(5) _cell_angle_gamma 83.493(4) _cell_volume 1161.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7046 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 25.979 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8661 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details 'SADABS-2007/4 (Bruker, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6737 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.73 _reflns_number_total 4786 _reflns_number_gt 3862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v6.45a (Bruker, 2005)' _computing_data_reduction 'SAINT v6.45a (Bruker, 2005)' _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^)+(0.0380P)^2^+0.6165P] 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 4786 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani 0.66406(11) 0.03028(4) 0.59454(4) 1.000 0.0274(2) . . S1 S Uani 0.95563(9) 0.50137(4) 0.37893(3) 1.000 0.0119(1) . . O1 O Uani 1.1237(3) 0.64651(10) 0.13849(9) 1.000 0.0143(4) . . O2 O Uani 1.1134(3) 0.52860(11) 0.17165(9) 1.000 0.0152(4) . . O3 O Uani 0.7422(3) 0.66974(11) 0.09961(9) 1.000 0.0155(4) . . O4 O Uani 1.2082(3) 0.49863(11) 0.35172(9) 1.000 0.0155(4) . . O5 O Uani 0.8560(3) 0.57089(11) 0.42474(9) 1.000 0.0164(4) . . C1 C Uani 0.9846(4) 0.69279(16) 0.06692(13) 1.000 0.0147(6) . . C2 C Uani 0.8736(4) 0.50268(16) 0.21191(13) 1.000 0.0135(6) . . C3 C Uani 0.7088(4) 0.55681(16) 0.14088(13) 1.000 0.0141(6) . . C4 C Uani 0.9990(4) 0.81344(16) 0.04037(14) 1.000 0.0179(6) . . C5 C Uani 1.2478(4) 0.85096(18) -0.00161(14) 1.000 0.0215(7) . . C6 C Uani 1.3349(5) 0.81535(18) -0.07835(14) 1.000 0.0237(7) . . C7 C Uani 1.3249(4) 0.69363(18) -0.05034(14) 1.000 0.0213(7) . . C8 C Uani 1.0769(4) 0.65619(17) -0.00864(13) 1.000 0.0179(7) . . C9 C Uani 0.7979(4) 0.54587(16) 0.28576(13) 1.000 0.0132(6) . . C10 C Uani 0.8743(4) 0.36836(16) 0.44288(13) 1.000 0.0128(6) . . C11 C Uani 0.6463(4) 0.35092(16) 0.48783(13) 1.000 0.0142(6) . . C12 C Uani 0.5819(4) 0.24607(17) 0.53553(13) 1.000 0.0162(6) . . C13 C Uani 0.7473(4) 0.16170(17) 0.53708(13) 1.000 0.0170(6) . . C14 C Uani 0.9762(4) 0.17860(17) 0.49409(13) 1.000 0.0175(6) . . C15 C Uani 1.0406(4) 0.28320(16) 0.44617(13) 1.000 0.0150(6) . . C16 C Uani 0.8685(4) 0.38112(16) 0.24147(13) 1.000 0.0131(6) . . C17 C Uani 0.6570(4) 0.33253(17) 0.28435(13) 1.000 0.0158(6) . . C18 C Uani 0.6443(4) 0.22163(17) 0.31090(13) 1.000 0.0176(7) . . C19 C Uani 0.8411(4) 0.15842(17) 0.29472(14) 1.000 0.0181(7) . . C20 C Uani 1.0513(4) 0.20724(17) 0.25173(14) 1.000 0.0179(7) . . C21 C Uani 1.0661(4) 0.31776(17) 0.22512(13) 1.000 0.0151(6) . . O6 O Uani -0.1616(3) 0.90807(15) 0.28090(14) 1.000 0.0427(7) . . N1 N Uani 0.2166(3) 0.85243(14) 0.24227(12) 1.000 0.0187(6) . . C22 C Uani -0.0005(4) 0.83856(19) 0.28715(17) 1.000 0.0267(8) . . C23 C Uani 0.2893(5) 0.95826(18) 0.18322(16) 1.000 0.0285(8) . . C24 C Uani 0.3953(4) 0.76352(17) 0.25456(15) 1.000 0.0212(7) . . H3A H Uiso 0.74240 0.52340 0.09640 1.000 0.0170 calc R H3B H Uiso 0.54080 0.54540 0.16740 1.000 0.0170 calc R H4A H Uiso 0.95390 0.83240 0.09280 1.000 0.0210 calc R H4B H Uiso 0.88320 0.85190 -0.00160 1.000 0.0210 calc R H5A H Uiso 1.36010 0.82080 0.04280 1.000 0.0260 calc R H5B H Uiso 1.24490 0.93050 -0.02250 1.000 0.0260 calc R H6A H Uiso 1.50100 0.83610 -0.10130 1.000 0.0280 calc R H6B H Uiso 1.23440 0.85260 -0.12590 1.000 0.0280 calc R H7A H Uiso 1.37190 0.67360 -0.10220 1.000 0.0250 calc R H7B H Uiso 1.44030 0.65650 -0.00790 1.000 0.0250 calc R H8A H Uiso 1.08100 0.57650 0.01310 1.000 0.0210 calc R H8B H Uiso 0.96600 0.68510 -0.05360 1.000 0.0210 calc R H9A H Uiso 0.62890 0.52960 0.30760 1.000 0.0160 calc R H9B H Uiso 0.80270 0.62530 0.25880 1.000 0.0160 calc R H11 H Uiso 0.53590 0.41000 0.48590 1.000 0.0170 calc R H12 H Uiso 0.42670 0.23230 0.56670 1.000 0.0190 calc R H14 H Uiso 1.08750 0.11940 0.49740 1.000 0.0210 calc R H15 H Uiso 1.19680 0.29670 0.41580 1.000 0.0180 calc R H17 H Uiso 0.52060 0.37520 0.29560 1.000 0.0190 calc R H18 H Uiso 0.49930 0.18900 0.34040 1.000 0.0210 calc R H19 H Uiso 0.83220 0.08270 0.31280 1.000 0.0220 calc R H20 H Uiso 1.18720 0.16440 0.24030 1.000 0.0210 calc R H21 H Uiso 1.21130 0.35010 0.19570 1.000 0.0180 calc R H22 H Uiso -0.03290 0.76790 0.32780 1.000 0.0320 calc R H23A H Uiso 0.15510 1.01130 0.18120 1.000 0.0430 calc R H23B H Uiso 0.33950 0.95750 0.12440 1.000 0.0430 calc R H23C H Uiso 0.42260 0.97750 0.20410 1.000 0.0430 calc R H24A H Uiso 0.32860 0.69750 0.29880 1.000 0.0320 calc R H24B H Uiso 0.53470 0.77970 0.27420 1.000 0.0320 calc R H24C H Uiso 0.44310 0.75330 0.19900 1.000 0.0320 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 0.0319(4) 0.0140(3) 0.0298(3) -0.0027(2) 0.0026(3) -0.0049(2) S1 0.0117(3) 0.0115(2) 0.0123(2) -0.0041(2) -0.0024(2) 0.0003(2) O1 0.0178(8) 0.0096(7) 0.0147(7) -0.0021(6) -0.0054(6) -0.0014(6) O2 0.0141(8) 0.0110(7) 0.0179(7) -0.0029(6) -0.0017(6) -0.0001(6) O3 0.0133(8) 0.0139(7) 0.0170(7) -0.0027(6) -0.0034(6) -0.0002(6) O4 0.0126(8) 0.0161(7) 0.0167(7) -0.0046(6) -0.0029(6) -0.0005(6) O5 0.0195(8) 0.0140(7) 0.0168(7) -0.0072(6) -0.0033(6) 0.0015(6) C1 0.0138(11) 0.0163(10) 0.0133(10) -0.0043(8) -0.0039(8) 0.0000(8) C2 0.0111(11) 0.0159(10) 0.0127(10) -0.0055(8) 0.0015(8) -0.0009(8) C3 0.0140(11) 0.0132(10) 0.0141(10) -0.0027(8) -0.0038(8) -0.0023(8) C4 0.0244(13) 0.0124(10) 0.0161(10) -0.0039(9) -0.0055(9) 0.0006(9) C5 0.0266(13) 0.0165(11) 0.0200(11) -0.0037(9) -0.0046(10) -0.0049(10) C6 0.0261(14) 0.0250(12) 0.0179(11) -0.0046(10) 0.0001(10) -0.0095(10) C7 0.0252(13) 0.0230(12) 0.0154(11) -0.0070(9) -0.0002(9) -0.0046(10) C8 0.0229(13) 0.0180(11) 0.0127(10) -0.0047(9) -0.0037(9) -0.0030(9) C9 0.0128(11) 0.0118(10) 0.0141(10) -0.0040(8) -0.0027(8) 0.0016(8) C10 0.0172(12) 0.0112(10) 0.0109(9) -0.0038(8) -0.0048(8) -0.0010(8) C11 0.0155(11) 0.0152(10) 0.0132(10) -0.0073(8) -0.0033(8) 0.0030(8) C12 0.0141(11) 0.0207(11) 0.0138(10) -0.0065(9) 0.0005(9) -0.0039(9) C13 0.0230(13) 0.0145(10) 0.0121(10) -0.0021(8) -0.0030(9) -0.0044(9) C14 0.0194(12) 0.0137(10) 0.0190(11) -0.0061(9) -0.0052(9) 0.0045(9) C15 0.0119(11) 0.0185(11) 0.0140(10) -0.0058(9) -0.0010(8) -0.0003(9) C16 0.0157(11) 0.0151(10) 0.0105(9) -0.0058(8) -0.0057(8) 0.0002(8) C17 0.0145(11) 0.0167(11) 0.0165(10) -0.0070(9) -0.0031(9) 0.0022(9) C18 0.0186(12) 0.0168(11) 0.0174(11) -0.0057(9) -0.0022(9) -0.0041(9) C19 0.0237(13) 0.0127(10) 0.0188(11) -0.0060(9) -0.0061(9) 0.0002(9) C20 0.0197(12) 0.0178(11) 0.0187(11) -0.0101(9) -0.0055(9) 0.0052(9) C21 0.0142(11) 0.0181(11) 0.0132(10) -0.0058(8) -0.0030(8) 0.0004(9) O6 0.0200(10) 0.0352(11) 0.0831(15) -0.0359(11) -0.0037(10) 0.0037(8) N1 0.0191(10) 0.0125(9) 0.0243(10) -0.0073(8) -0.0031(8) 0.0014(7) C22 0.0213(14) 0.0225(12) 0.0430(15) -0.0193(11) -0.0022(11) -0.0046(10) C23 0.0392(16) 0.0154(12) 0.0272(13) -0.0052(10) -0.0007(11) -0.0012(11) C24 0.0213(13) 0.0183(11) 0.0250(12) -0.0094(10) -0.0050(10) 0.0029(9) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C13 1.736(2) . . yes S1 O4 1.4376(18) . . yes S1 O5 1.4395(17) . . yes S1 C9 1.782(2) . . yes S1 C10 1.767(2) . . yes O1 O2 1.471(2) . . yes O1 C1 1.432(3) . . yes O2 C2 1.440(3) . . yes O3 C1 1.423(3) . . yes O3 C3 1.428(3) . . yes O6 C22 1.220(3) . . yes N1 C24 1.452(3) . . yes N1 C23 1.448(3) . . yes N1 C22 1.332(3) . . yes C1 C8 1.521(3) . . no C1 C4 1.519(3) . . no C2 C9 1.538(3) . . no C2 C16 1.519(3) . . no C2 C3 1.531(3) . . no C4 C5 1.525(3) . . no C5 C6 1.526(3) . . no C6 C7 1.527(4) . . no C7 C8 1.520(3) . . no C10 C15 1.391(3) . . no C10 C11 1.388(3) . . no C11 C12 1.386(3) . . no C12 C13 1.385(3) . . no C13 C14 1.381(3) . . no C14 C15 1.384(3) . . no C16 C17 1.391(3) . . no C16 C21 1.389(3) . . no C17 C18 1.391(3) . . no C18 C19 1.384(3) . . no C19 C20 1.386(3) . . no C20 C21 1.388(3) . . no C3 H3A 0.9900 . . no C3 H3B 0.9900 . . no C4 H4A 0.9900 . . no C4 H4B 0.9900 . . no C5 H5B 0.9900 . . no C5 H5A 0.9900 . . no C6 H6A 0.9900 . . no C6 H6B 0.9900 . . no C7 H7A 0.9900 . . no C7 H7B 0.9900 . . no C8 H8B 0.9900 . . no C8 H8A 0.9900 . . no C9 H9B 0.9900 . . no C9 H9A 0.9900 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C17 H17 0.9500 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21 0.9500 . . no C22 H22 0.9500 . . no C23 H23A 0.9800 . . no C23 H23B 0.9800 . . no C23 H23C 0.9800 . . no C24 H24A 0.9800 . . no C24 H24B 0.9800 . . no C24 H24C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O5 118.92(10) . . . yes O4 S1 C9 110.00(9) . . . yes O4 S1 C10 108.36(10) . . . yes O5 S1 C9 103.56(10) . . . yes O5 S1 C10 108.98(10) . . . yes C9 S1 C10 106.32(10) . . . yes O2 O1 C1 108.29(15) . . . yes O1 O2 C2 107.69(15) . . . yes C1 O3 C3 112.76(17) . . . yes C23 N1 C24 117.09(19) . . . yes C22 N1 C23 121.3(2) . . . yes C22 N1 C24 121.5(2) . . . yes O1 C1 C4 103.94(17) . . . yes O3 C1 C8 112.63(18) . . . yes O1 C1 C8 112.77(18) . . . yes O3 C1 C4 106.63(18) . . . yes O1 C1 O3 108.39(16) . . . yes C4 C1 C8 111.94(17) . . . no O2 C2 C16 105.87(18) . . . yes C3 C2 C16 109.12(18) . . . no C9 C2 C16 114.21(17) . . . no C3 C2 C9 108.53(18) . . . no O2 C2 C3 107.36(16) . . . yes O2 C2 C9 111.52(18) . . . yes O3 C3 C2 110.89(18) . . . yes C1 C4 C5 112.34(19) . . . no C4 C5 C6 111.3(2) . . . no C5 C6 C7 111.11(18) . . . no C6 C7 C8 111.7(2) . . . no C1 C8 C7 112.07(19) . . . no S1 C9 C2 120.64(16) . . . yes S1 C10 C11 119.57(17) . . . yes S1 C10 C15 118.94(17) . . . yes C11 C10 C15 121.5(2) . . . no C10 C11 C12 119.1(2) . . . no C11 C12 C13 119.0(2) . . . no Cl1 C13 C12 118.97(17) . . . yes Cl1 C13 C14 118.85(18) . . . yes C12 C13 C14 122.2(2) . . . no C13 C14 C15 118.9(2) . . . no C10 C15 C14 119.3(2) . . . no C2 C16 C17 118.6(2) . . . no C17 C16 C21 119.2(2) . . . no C2 C16 C21 122.1(2) . . . no C16 C17 C18 120.3(2) . . . no C17 C18 C19 120.6(2) . . . no C18 C19 C20 119.0(2) . . . no C19 C20 C21 120.9(2) . . . no C16 C21 C20 120.0(2) . . . no C2 C3 H3B 109.00 . . . no H3A C3 H3B 108.00 . . . no O3 C3 H3B 109.00 . . . no C2 C3 H3A 109.00 . . . no O3 C3 H3A 109.00 . . . no C1 C4 H4A 109.00 . . . no C1 C4 H4B 109.00 . . . no H4A C4 H4B 108.00 . . . no C5 C4 H4A 109.00 . . . no C5 C4 H4B 109.00 . . . no C4 C5 H5B 109.00 . . . no H5A C5 H5B 108.00 . . . no C6 C5 H5A 109.00 . . . no C6 C5 H5B 109.00 . . . no C4 C5 H5A 109.00 . . . no C7 C6 H6B 109.00 . . . no H6A C6 H6B 108.00 . . . no C5 C6 H6B 109.00 . . . no C7 C6 H6A 109.00 . . . no C5 C6 H6A 109.00 . . . no C6 C7 H7A 109.00 . . . no C6 C7 H7B 109.00 . . . no H7A C7 H7B 108.00 . . . no C8 C7 H7B 109.00 . . . no C8 C7 H7A 109.00 . . . no C7 C8 H8A 109.00 . . . no C1 C8 H8B 109.00 . . . no C1 C8 H8A 109.00 . . . no C7 C8 H8B 109.00 . . . no H8A C8 H8B 108.00 . . . no S1 C9 H9A 107.00 . . . no H9A C9 H9B 107.00 . . . no S1 C9 H9B 107.00 . . . no C2 C9 H9A 107.00 . . . no C2 C9 H9B 107.00 . . . no C10 C11 H11 120.00 . . . no C12 C11 H11 120.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 121.00 . . . no C15 C14 H14 121.00 . . . no C13 C14 H14 121.00 . . . no C14 C15 H15 120.00 . . . no C10 C15 H15 120.00 . . . no C16 C17 H17 120.00 . . . no C18 C17 H17 120.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 120.00 . . . no C20 C19 H19 121.00 . . . no C18 C19 H19 120.00 . . . no C19 C20 H20 120.00 . . . no C21 C20 H20 120.00 . . . no C16 C21 H21 120.00 . . . no C20 C21 H21 120.00 . . . no O6 C22 N1 126.1(2) . . . yes O6 C22 H22 117.00 . . . no N1 C22 H22 117.00 . . . no N1 C23 H23A 109.00 . . . no N1 C23 H23B 109.00 . . . no N1 C23 H23C 109.00 . . . no H23A C23 H23B 110.00 . . . no H23A C23 H23C 110.00 . . . no H23B C23 H23C 109.00 . . . no N1 C24 H24A 109.00 . . . no N1 C24 H24B 109.00 . . . no N1 C24 H24C 109.00 . . . no H24A C24 H24B 109.00 . . . no H24A C24 H24C 109.00 . . . no H24B C24 H24C 109.00 . . . no 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 O4 S1 C9 C2 43.5(2) . . . . no O5 S1 C9 C2 171.62(17) . . . . no C10 S1 C9 C2 -73.60(19) . . . . no O4 S1 C10 C11 170.54(17) . . . . no O4 S1 C10 C15 -10.1(2) . . . . no O5 S1 C10 C11 39.8(2) . . . . no O5 S1 C10 C15 -140.90(17) . . . . no C9 S1 C10 C11 -71.26(19) . . . . no C9 S1 C10 C15 108.06(18) . . . . no C1 O1 O2 C2 -68.38(18) . . . . no O2 O1 C1 O3 64.63(19) . . . . no O2 O1 C1 C4 177.79(15) . . . . no O2 O1 C1 C8 -60.8(2) . . . . no O1 O2 C2 C3 61.10(19) . . . . no O1 O2 C2 C9 -57.66(19) . . . . no O1 O2 C2 C16 177.56(14) . . . . no C3 O3 C1 O1 -58.6(2) . . . . no C3 O3 C1 C4 -169.99(16) . . . . no C3 O3 C1 C8 66.9(2) . . . . no C1 O3 C3 C2 53.7(2) . . . . no C24 N1 C22 O6 -179.7(2) . . . . no C23 N1 C22 O6 4.4(4) . . . . no O3 C1 C4 C5 -176.33(16) . . . . no O1 C1 C4 C5 69.3(2) . . . . no O3 C1 C8 C7 172.82(18) . . . . no C4 C1 C8 C7 52.7(3) . . . . no C8 C1 C4 C5 -52.7(2) . . . . no O1 C1 C8 C7 -64.1(2) . . . . no C16 C2 C3 O3 -168.99(17) . . . . no O2 C2 C3 O3 -54.7(2) . . . . no C9 C2 C3 O3 66.0(2) . . . . no C16 C2 C9 S1 59.1(2) . . . . no O2 C2 C16 C17 179.05(18) . . . . no O2 C2 C16 C21 -2.6(3) . . . . no C3 C2 C16 C17 -65.7(2) . . . . no C3 C2 C16 C21 112.7(2) . . . . no C9 C2 C16 C17 56.0(3) . . . . no C9 C2 C16 C21 -125.6(2) . . . . no O2 C2 C9 S1 -60.9(2) . . . . no C3 C2 C9 S1 -178.99(15) . . . . no C1 C4 C5 C6 54.0(2) . . . . no C4 C5 C6 C7 -54.9(3) . . . . no C5 C6 C7 C8 55.2(3) . . . . no C6 C7 C8 C1 -54.1(2) . . . . no S1 C10 C15 C14 -178.18(16) . . . . no S1 C10 C11 C12 177.94(16) . . . . no C15 C10 C11 C12 -1.4(3) . . . . no C11 C10 C15 C14 1.1(3) . . . . no C10 C11 C12 C13 0.1(3) . . . . no C11 C12 C13 C14 1.4(3) . . . . no C11 C12 C13 Cl1 -178.36(16) . . . . no Cl1 C13 C14 C15 178.13(16) . . . . no C12 C13 C14 C15 -1.6(3) . . . . no C13 C14 C15 C10 0.3(3) . . . . no C2 C16 C17 C18 178.78(19) . . . . no C17 C16 C21 C20 -0.2(3) . . . . no C21 C16 C17 C18 0.3(3) . . . . no C2 C16 C21 C20 -178.59(19) . . . . no C16 C17 C18 C19 -0.3(3) . . . . no C17 C18 C19 C20 0.1(3) . . . . no C18 C19 C20 C21 0.1(3) . . . . no C19 C20 C21 C16 0.0(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C3 H3B O2 0.9900 2.4500 3.387(3) 157.00 1_455 yes C8 H8A O2 0.9900 2.5000 2.858(3) 101.00 . yes C9 H9A O4 0.9900 2.4200 3.413(3) 176.00 1_455 yes C9 H9B O1 0.9900 2.4400 2.806(3) 101.00 . yes C9 H9B O3 0.9900 2.5600 2.952(3) 104.00 . yes C11 H11 O5 0.9500 2.5200 3.253(3) 134.00 2_666 yes C15 H15 O4 0.9500 2.5100 2.905(3) 105.00 . yes C19 H19 O6 0.9500 2.6000 3.467(3) 152.00 1_645 yes C21 H21 O2 0.9500 2.3000 2.660(3) 102.00 . yes C23 H23A O6 0.9800 2.4100 2.814(3) 104.00 . yes _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.333 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.060 # Attachment 'rka269_Cl_H2O.cif' data_rka269 _database_code_depnum_ccdc_archive 'CCDC 680268' #TrackingRef 'rka269_Cl_H2O.cif' _audit_update_record ; 2008-03-04 # Formatted by J.Bacsa ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common RKA269 _chemical_melting_point ? _chemical_formula_moiety 'C22 H37 N2 O4, H2 O, Cl' _chemical_formula_sum 'C22 H39 Cl N2 O5' _chemical_formula_weight 447.00 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 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 18.705(3) _cell_length_b 7.6876(13) _cell_length_c 16.257(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.288(3) _cell_angle_gamma 90.00 _cell_volume 2333.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10985 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9074 _exptl_absorpt_correction_T_max 0.9804 _exptl_absorpt_process_details 'SADABS-2007/4 (Bruker, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14079 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4241 _reflns_number_gt 3573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v6.45a (Bruker, 2005)' _computing_data_reduction 'SAINT v6.45a (Bruker, 2005)' _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^)+(0.0617P)^2^+3.6453P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4241 _refine_ls_number_parameters 293 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1611 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.81413(13) 0.0778(3) 0.39824(14) 1.000 0.0250(8) . . O2 O Uani 0.83545(13) 0.2081(3) 0.46133(15) 1.000 0.0264(8) . . O3 O Uani 0.80147(12) -0.1318(3) 0.49626(14) 1.000 0.0219(7) . . O4 O Uani 0.56728(12) 0.2745(3) 0.49708(13) 1.000 0.0184(7) . . N1 N Uani 0.58338(14) 0.3883(3) 0.37295(15) 1.000 0.0154(8) . . N2 N Uani 0.38585(14) 0.3252(3) 0.32264(15) 1.000 0.0170(8) . . C1 C Uani 0.83851(18) -0.0877(4) 0.4261(2) 1.000 0.0196(10) . . C2 C Uani 0.81421(18) -0.2150(5) 0.3592(2) 1.000 0.0224(11) . . C3 C Uani 0.8493(2) -0.1687(5) 0.2790(2) 1.000 0.0311(11) . . C4 C Uani 0.9300(2) -0.1783(6) 0.2931(2) 1.000 0.0373(14) . . C5 C Uani 0.9539(2) -0.0485(6) 0.3599(2) 1.000 0.0332(12) . . C6 C Uani 0.91988(18) -0.0946(5) 0.4403(2) 1.000 0.0240(11) . . C7 C Uani 0.83620(19) -0.3978(5) 0.3860(2) 1.000 0.0281(12) . . C8 C Uani 0.9174(2) -0.4063(5) 0.3994(3) 1.000 0.0350(12) . . C9 C Uani 0.9413(2) -0.2785(5) 0.4674(2) 1.000 0.0309(12) . . C10 C Uani 0.9516(2) -0.3597(6) 0.3199(3) 1.000 0.0398(14) . . C11 C Uani 0.81202(18) -0.0085(5) 0.5608(2) 1.000 0.0213(10) . . C12 C Uani 0.79541(18) 0.1739(4) 0.5319(2) 1.000 0.0194(10) . . C13 C Uani 0.71637(18) 0.2045(4) 0.5153(2) 1.000 0.0196(10) . . C14 C Uani 0.68552(19) 0.2754(4) 0.4494(2) 1.000 0.0176(10) . . C15 C Uani 0.60816(17) 0.3109(4) 0.44302(18) 1.000 0.0145(9) . . C16 C Uani 0.8241(2) 0.3012(5) 0.5968(2) 1.000 0.0308(12) . . C17 C Uani 0.50961(17) 0.4420(4) 0.36055(18) 1.000 0.0140(9) . . C18 C Uani 0.46416(17) 0.2882(4) 0.33027(18) 1.000 0.0145(9) . . C20 C Uani 0.35396(19) 0.3722(5) 0.4018(2) 1.000 0.0244(11) . . C21 C Uani 0.3745(2) 0.2504(5) 0.4716(2) 1.000 0.0276(11) . . C22 C Uani 0.3633(2) 0.4579(4) 0.2584(2) 1.000 0.0232(11) . . C23 C Uani 0.3835(2) 0.4043(5) 0.1738(2) 1.000 0.0250(11) . . O1W O Uani 0.44550(13) -0.1648(3) 0.34317(14) 1.000 0.0245(8) . . Cl1 Cl Uani 0.30671(4) -0.00603(10) 0.26567(5) 1.000 0.0184(2) . . H1 H Uiso 0.61290 0.40670 0.33360 1.000 0.029(11) calc R H2 H Uiso 0.76090 -0.20930 0.35000 1.000 0.0270 calc R H2N H Uiso 0.36400 0.22150 0.30560 1.000 0.024(10) calc R H3A H Uiso 0.83320 -0.25090 0.23490 1.000 0.0380 calc R H3B H Uiso 0.83510 -0.04980 0.26130 1.000 0.0380 calc R H4 H Uiso 0.95310 -0.14870 0.24090 1.000 0.0450 calc R H5A H Uiso 0.93950 0.07040 0.34250 1.000 0.0400 calc R H5B H Uiso 1.00680 -0.05100 0.36840 1.000 0.0400 calc R H6 H Uiso 0.93570 -0.00960 0.48420 1.000 0.0290 calc R H7A H Uiso 0.81980 -0.48250 0.34300 1.000 0.0340 calc R H7B H Uiso 0.81360 -0.42820 0.43760 1.000 0.0340 calc R H8 H Uiso 0.93200 -0.52680 0.41640 1.000 0.0420 calc R H9A H Uiso 0.99380 -0.28520 0.47810 1.000 0.0370 calc R H9B H Uiso 0.91830 -0.30840 0.51890 1.000 0.0370 calc R H10A H Uiso 1.00440 -0.36640 0.32830 1.000 0.0480 calc R H10B H Uiso 0.93620 -0.44380 0.27630 1.000 0.0480 calc R H11A H Uiso 0.86240 -0.01420 0.58300 1.000 0.0260 calc R H11B H Uiso 0.78090 -0.03870 0.60590 1.000 0.0260 calc R H13 H Uiso 0.689(2) 0.167(5) 0.559(2) 1.000 0.030(10) . . H14 H Uiso 0.708(2) 0.312(5) 0.407(2) 1.000 0.024(10) . . H16A H Uiso 0.87590 0.28550 0.60580 1.000 0.0470 calc R H16B H Uiso 0.80090 0.28010 0.64840 1.000 0.0470 calc R H16C H Uiso 0.81400 0.42030 0.57800 1.000 0.0470 calc R H17A H Uiso 0.50570 0.53710 0.31950 1.000 0.0170 calc R H17B H Uiso 0.49210 0.48600 0.41300 1.000 0.0170 calc R H18A H Uiso 0.47990 0.25140 0.27580 1.000 0.0170 calc R H18B H Uiso 0.47270 0.18980 0.36890 1.000 0.0170 calc R H20A H Uiso 0.30110 0.37320 0.39300 1.000 0.0290 calc R H20B H Uiso 0.36940 0.49140 0.41760 1.000 0.0290 calc R H21A H Uiso 0.36520 0.13020 0.45400 1.000 0.0410 calc R H21B H Uiso 0.34620 0.27730 0.51880 1.000 0.0410 calc R H21C H Uiso 0.42550 0.26430 0.48740 1.000 0.0410 calc R H22A H Uiso 0.38620 0.57080 0.27290 1.000 0.0280 calc R H22B H Uiso 0.31070 0.47400 0.25800 1.000 0.0280 calc R H23A H Uiso 0.43540 0.41560 0.17020 1.000 0.0380 calc R H23B H Uiso 0.35900 0.47930 0.13250 1.000 0.0380 calc R H23C H Uiso 0.36930 0.28310 0.16380 1.000 0.0380 calc R H1WA H Uiso 0.3992(11) -0.124(6) 0.320(2) 1.000 0.052(14) . . H1WB H Uiso 0.4380(19) -0.184(6) 0.4015(9) 1.000 0.053(14) . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0333(15) 0.0201(13) 0.0211(12) 0.0021(10) -0.0027(10) -0.0005(10) O2 0.0274(14) 0.0243(13) 0.0276(13) -0.0012(11) 0.0034(11) -0.0023(11) O3 0.0241(13) 0.0206(12) 0.0216(12) 0.0035(10) 0.0078(10) -0.0002(10) O4 0.0190(12) 0.0227(12) 0.0141(11) 0.0033(9) 0.0058(9) 0.0016(9) N1 0.0200(15) 0.0156(14) 0.0110(13) 0.0010(10) 0.0051(11) 0.0013(11) N2 0.0226(15) 0.0147(14) 0.0136(13) -0.0043(11) 0.0014(11) -0.0004(11) C1 0.0221(18) 0.0174(17) 0.0195(17) 0.0050(13) 0.0018(14) 0.0017(13) C2 0.0130(17) 0.030(2) 0.0241(18) -0.0003(15) -0.0007(14) -0.0030(14) C3 0.036(2) 0.034(2) 0.0231(19) -0.0023(16) 0.0001(16) 0.0012(17) C4 0.034(2) 0.053(3) 0.026(2) -0.0118(19) 0.0126(17) -0.009(2) C5 0.022(2) 0.043(2) 0.036(2) -0.0091(18) 0.0127(17) -0.0078(17) C6 0.0212(19) 0.0241(19) 0.0266(19) -0.0047(15) 0.0005(15) 0.0007(14) C7 0.026(2) 0.025(2) 0.033(2) -0.0010(16) -0.0014(16) 0.0015(15) C8 0.034(2) 0.025(2) 0.045(2) -0.0096(18) -0.0069(18) 0.0063(17) C9 0.021(2) 0.034(2) 0.037(2) -0.0007(17) -0.0051(16) 0.0077(16) C10 0.025(2) 0.051(3) 0.043(2) -0.024(2) -0.0004(18) 0.0029(19) C11 0.0158(17) 0.0286(19) 0.0196(16) 0.0026(14) 0.0020(13) 0.0035(14) C12 0.0180(18) 0.0235(18) 0.0167(16) -0.0012(14) 0.0020(13) -0.0009(13) C13 0.0219(19) 0.0167(17) 0.0205(17) -0.0020(13) 0.0050(14) -0.0003(13) C14 0.026(2) 0.0129(16) 0.0142(16) -0.0050(13) 0.0040(14) -0.0019(13) C15 0.0219(18) 0.0105(15) 0.0113(15) -0.0037(12) 0.0039(13) -0.0012(13) C16 0.030(2) 0.034(2) 0.028(2) -0.0098(17) -0.0016(16) -0.0005(17) C17 0.0231(17) 0.0086(14) 0.0102(14) 0.0027(12) 0.0006(12) 0.0010(12) C18 0.0226(18) 0.0110(15) 0.0098(14) -0.0018(12) -0.0003(12) 0.0015(13) C20 0.0215(19) 0.030(2) 0.0221(18) -0.0133(15) 0.0057(14) -0.0005(15) C21 0.033(2) 0.034(2) 0.0166(17) -0.0056(15) 0.0092(15) -0.0101(16) C22 0.029(2) 0.0143(17) 0.0254(18) 0.0028(14) -0.0062(15) 0.0010(14) C23 0.030(2) 0.0219(18) 0.0227(18) 0.0065(14) -0.0023(15) -0.0018(15) O1W 0.0327(15) 0.0245(13) 0.0167(12) 0.0071(10) 0.0057(10) 0.0048(11) Cl1 0.0224(4) 0.0187(4) 0.0144(4) -0.0020(3) 0.0036(3) -0.0011(3) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 O2 1.472(3) . . yes O1 C1 1.417(4) . . yes O2 C12 1.430(4) . . yes O3 C1 1.410(4) . . yes O3 C11 1.419(4) . . yes O4 C15 1.230(4) . . yes O1W H1WB 0.978(17) . . no O1W H1WA 0.98(3) . . no N1 C15 1.344(4) . . yes N1 C17 1.443(4) . . yes N2 C22 1.503(4) . . yes N2 C20 1.494(4) . . yes N2 C18 1.490(4) . . yes N1 H1 0.8800 . . no N2 H2N 0.9300 . . no C1 C6 1.527(5) . . no C1 C2 1.513(5) . . no C2 C3 1.535(5) . . no C2 C7 1.521(5) . . no C3 C4 1.516(5) . . no C4 C10 1.509(6) . . no C4 C5 1.523(6) . . no C5 C6 1.528(5) . . no C6 C9 1.527(5) . . no C7 C8 1.523(5) . . no C8 C9 1.527(6) . . no C8 C10 1.518(7) . . no C11 C12 1.506(5) . . no C12 C16 1.515(5) . . no C12 C13 1.506(5) . . no C13 C14 1.307(5) . . no C14 C15 1.470(5) . . no C17 C18 1.522(4) . . no C20 C21 1.504(5) . . no C22 C23 1.505(5) . . no C2 H2 1.0000 . . no C3 H3A 0.9900 . . no C3 H3B 0.9900 . . no C4 H4 1.0000 . . no C5 H5B 0.9900 . . no C5 H5A 0.9900 . . no C6 H6 1.0000 . . no C7 H7B 0.9900 . . no C7 H7A 0.9900 . . no C8 H8 1.0000 . . no C9 H9A 0.9900 . . no C9 H9B 0.9900 . . no C10 H10A 0.9900 . . no C10 H10B 0.9900 . . no C11 H11B 0.9900 . . no C11 H11A 0.9900 . . no C13 H13 0.94(3) . . no C14 H14 0.87(4) . . no C16 H16B 0.9800 . . no C16 H16A 0.9800 . . no C16 H16C 0.9800 . . no C17 H17A 0.9900 . . no C17 H17B 0.9900 . . no C18 H18B 0.9900 . . no C18 H18A 0.9900 . . no C20 H20A 0.9900 . . no C20 H20B 0.9900 . . no C21 H21A 0.9800 . . no C21 H21C 0.9800 . . no C21 H21B 0.9800 . . no C22 H22B 0.9900 . . no C22 H22A 0.9900 . . no C23 H23C 0.9800 . . no C23 H23A 0.9800 . . no C23 H23B 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 O1 C1 108.6(2) . . . yes O1 O2 C12 107.5(2) . . . yes C1 O3 C11 112.6(2) . . . yes H1WA O1W H1WB 104(3) . . . no C15 N1 C17 121.7(3) . . . yes C18 N2 C20 114.4(2) . . . yes C20 N2 C22 108.9(2) . . . yes C18 N2 C22 115.0(2) . . . yes C17 N1 H1 119.00 . . . no C15 N1 H1 119.00 . . . no C18 N2 H2N 106.00 . . . no C20 N2 H2N 106.00 . . . no C22 N2 H2N 106.00 . . . no O1 C1 O3 108.1(3) . . . yes O1 C1 C6 112.3(3) . . . yes O3 C1 C2 106.5(3) . . . yes C2 C1 C6 110.0(3) . . . no O1 C1 C2 105.8(3) . . . yes O3 C1 C6 113.7(3) . . . yes C1 C2 C3 109.6(3) . . . no C1 C2 C7 109.1(3) . . . no C3 C2 C7 109.6(3) . . . no C2 C3 C4 109.3(3) . . . no C5 C4 C10 109.7(3) . . . no C3 C4 C10 109.7(3) . . . no C3 C4 C5 109.0(3) . . . no C4 C5 C6 109.8(3) . . . no C1 C6 C9 108.6(3) . . . no C5 C6 C9 110.3(3) . . . no C1 C6 C5 108.8(3) . . . no C2 C7 C8 109.4(3) . . . no C7 C8 C9 108.9(3) . . . no C7 C8 C10 109.5(3) . . . no C9 C8 C10 110.2(3) . . . no C6 C9 C8 109.0(3) . . . no C4 C10 C8 110.2(3) . . . no O3 C11 C12 112.0(3) . . . yes C13 C12 C16 109.2(3) . . . no O2 C12 C13 112.4(3) . . . yes O2 C12 C11 108.3(3) . . . yes C11 C12 C16 109.0(3) . . . no C11 C12 C13 112.6(3) . . . no O2 C12 C16 105.0(3) . . . yes C12 C13 C14 126.5(3) . . . no C13 C14 C15 121.5(3) . . . no O4 C15 C14 123.9(3) . . . yes O4 C15 N1 120.5(3) . . . yes N1 C15 C14 115.6(3) . . . yes N1 C17 C18 109.6(2) . . . yes N2 C18 C17 114.0(2) . . . yes N2 C20 C21 113.7(3) . . . yes N2 C22 C23 112.0(3) . . . yes C3 C2 H2 110.00 . . . no C7 C2 H2 110.00 . . . no C1 C2 H2 110.00 . . . no C2 C3 H3B 110.00 . . . no C4 C3 H3A 110.00 . . . no C2 C3 H3A 110.00 . . . no H3A C3 H3B 108.00 . . . no C4 C3 H3B 110.00 . . . no C5 C4 H4 109.00 . . . no C10 C4 H4 109.00 . . . no C3 C4 H4 110.00 . . . no C4 C5 H5B 110.00 . . . no C6 C5 H5A 110.00 . . . no C4 C5 H5A 110.00 . . . no H5A C5 H5B 108.00 . . . no C6 C5 H5B 110.00 . . . no C1 C6 H6 110.00 . . . no C5 C6 H6 110.00 . . . no C9 C6 H6 110.00 . . . no C2 C7 H7A 110.00 . . . no C2 C7 H7B 110.00 . . . no C8 C7 H7B 110.00 . . . no H7A C7 H7B 108.00 . . . no C8 C7 H7A 110.00 . . . no C9 C8 H8 109.00 . . . no C10 C8 H8 109.00 . . . no C7 C8 H8 109.00 . . . no C6 C9 H9A 110.00 . . . no C8 C9 H9A 110.00 . . . no C8 C9 H9B 110.00 . . . no C6 C9 H9B 110.00 . . . no H9A C9 H9B 108.00 . . . no C4 C10 H10B 110.00 . . . no C8 C10 H10A 110.00 . . . no C4 C10 H10A 110.00 . . . no H10A C10 H10B 108.00 . . . no C8 C10 H10B 110.00 . . . no O3 C11 H11A 109.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no H11A C11 H11B 108.00 . . . no O3 C11 H11B 109.00 . . . no C12 C13 H13 113(2) . . . no C14 C13 H13 121(2) . . . no C13 C14 H14 125(2) . . . no C15 C14 H14 114(2) . . . no C12 C16 H16B 109.00 . . . no C12 C16 H16C 109.00 . . . no H16A C16 H16B 110.00 . . . no H16A C16 H16C 109.00 . . . no H16B C16 H16C 110.00 . . . no C12 C16 H16A 109.00 . . . no N1 C17 H17A 110.00 . . . no C18 C17 H17A 110.00 . . . no C18 C17 H17B 110.00 . . . no H17A C17 H17B 108.00 . . . no N1 C17 H17B 110.00 . . . no N2 C18 H18A 109.00 . . . no N2 C18 H18B 109.00 . . . no C17 C18 H18B 109.00 . . . no H18A C18 H18B 108.00 . . . no C17 C18 H18A 109.00 . . . no N2 C20 H20B 109.00 . . . no C21 C20 H20A 109.00 . . . no C21 C20 H20B 109.00 . . . no H20A C20 H20B 108.00 . . . no N2 C20 H20A 109.00 . . . no C20 C21 H21A 109.00 . . . no C20 C21 H21B 109.00 . . . no H21A C21 H21B 109.00 . . . no H21A C21 H21C 109.00 . . . no H21B C21 H21C 109.00 . . . no C20 C21 H21C 109.00 . . . no N2 C22 H22A 109.00 . . . no C23 C22 H22A 109.00 . . . no C23 C22 H22B 109.00 . . . no N2 C22 H22B 109.00 . . . no H22A C22 H22B 108.00 . . . no C22 C23 H23B 109.00 . . . no C22 C23 H23C 109.00 . . . no C22 C23 H23A 109.00 . . . no H23A C23 H23C 110.00 . . . no H23B C23 H23C 110.00 . . . no H23A C23 H23B 109.00 . . . no 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 C1 O1 O2 C12 -67.7(3) . . . . no O2 O1 C1 O3 65.5(3) . . . . no O2 O1 C1 C2 179.4(2) . . . . no O2 O1 C1 C6 -60.6(3) . . . . no O1 O2 C12 C11 58.9(3) . . . . no O1 O2 C12 C13 -66.1(3) . . . . no O1 O2 C12 C16 175.3(2) . . . . no C11 O3 C1 O1 -58.9(3) . . . . no C11 O3 C1 C2 -172.2(3) . . . . no C11 O3 C1 C6 66.5(3) . . . . no C1 O3 C11 C12 52.8(3) . . . . no C17 N1 C15 O4 4.2(4) . . . . no C17 N1 C15 C14 -175.6(3) . . . . no C15 N1 C17 C18 -83.8(3) . . . . no C20 N2 C18 C17 -61.9(3) . . . . no C22 N2 C18 C17 65.4(3) . . . . no C18 N2 C20 C21 -48.2(4) . . . . no C22 N2 C20 C21 -178.5(3) . . . . no C18 N2 C22 C23 59.1(4) . . . . no C20 N2 C22 C23 -170.9(3) . . . . no O1 C1 C2 C3 62.0(3) . . . . no O1 C1 C2 C7 -178.0(3) . . . . no O3 C1 C2 C3 176.9(3) . . . . no O3 C1 C2 C7 -63.1(3) . . . . no C6 C1 C2 C3 -59.5(4) . . . . no C6 C1 C2 C7 60.5(3) . . . . no O1 C1 C6 C5 -58.2(4) . . . . no O1 C1 C6 C9 -178.2(3) . . . . no O3 C1 C6 C5 178.8(3) . . . . no O3 C1 C6 C9 58.7(3) . . . . no C2 C1 C6 C5 59.4(4) . . . . no C2 C1 C6 C9 -60.6(3) . . . . no C1 C2 C3 C4 60.1(4) . . . . no C7 C2 C3 C4 -59.6(4) . . . . no C1 C2 C7 C8 -60.5(4) . . . . no C3 C2 C7 C8 59.5(4) . . . . no C2 C3 C4 C5 -60.5(4) . . . . no C2 C3 C4 C10 59.5(4) . . . . no C3 C4 C5 C6 61.2(4) . . . . no C10 C4 C5 C6 -58.9(4) . . . . no C3 C4 C10 C8 -60.1(4) . . . . no C5 C4 C10 C8 59.5(4) . . . . no C4 C5 C6 C1 -60.1(4) . . . . no C4 C5 C6 C9 58.9(4) . . . . no C1 C6 C9 C8 60.7(4) . . . . no C5 C6 C9 C8 -58.5(4) . . . . no C2 C7 C8 C9 61.1(4) . . . . no C2 C7 C8 C10 -59.4(4) . . . . no C7 C8 C9 C6 -61.3(4) . . . . no C10 C8 C9 C6 58.8(4) . . . . no C7 C8 C10 C4 59.9(4) . . . . no C9 C8 C10 C4 -59.9(4) . . . . no O3 C11 C12 O2 -53.0(3) . . . . no O3 C11 C12 C13 72.0(3) . . . . no O3 C11 C12 C16 -166.7(3) . . . . no O2 C12 C13 C14 -8.6(5) . . . . no C11 C12 C13 C14 -131.3(3) . . . . no C16 C12 C13 C14 107.5(4) . . . . no C12 C13 C14 C15 -175.1(3) . . . . no C13 C14 C15 O4 -1.5(5) . . . . no C13 C14 C15 N1 178.3(3) . . . . no N1 C17 C18 N2 174.8(2) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 Cl1 0.8800 2.3700 3.240(3) 172.00 2_655 yes O1W H1WA Cl1 0.98(3) 2.10(3) 3.073(3) 172(3) . yes O1W H1WB O4 0.978(17) 1.80(2) 2.754(3) 165(4) 3_656 yes N2 H2N Cl1 0.9300 2.1300 3.062(3) 176.00 . yes C11 H11B Cl1 0.9900 2.7500 3.691(3) 159.00 3_656 yes C17 H17A O1W 0.9900 2.5900 3.258(4) 125.00 1_565 yes C18 H18A O1W 0.9900 2.5300 3.389(4) 145.00 2_655 yes C20 H20B O4 0.9900 2.5300 3.460(4) 157.00 3_666 yes C22 H22A O1W 0.9900 2.5500 3.526(4) 167.00 1_565 yes C23 H23A O1W 0.9800 2.3300 3.270(5) 159.00 2_655 yes _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.771 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.078