# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _publ_requested_journal 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _journal_volume ? _journal_year ? _journal_page_first ? _publ_contact_author_name 'Juliusz Pernak' _publ_contact_author_address ;Poznan University of Technology Faculty of Chemical Technology Poznan, Poland ; _publ_section_title ; Synthesis and Properties of Chiral Imidazolium Ionic Liquids with a (1R,2S,5R)-(--)-Menthoxymethyl Substituent ; loop_ _publ_author_name _publ_author_address 'Pernak, Juliusz' ;Poznan University of Technology Faculty of Chemical Technology Poznan, Poland ; 'Feder-Kubis, J.' ;Poznan University of Technology Faculty of Chemical Technology Poznan, Poland ; 'Cieniecka-Roslonkiewicz, A.' ;Institute of Industrial Organic Chemistry Warsaw, Poland ; 'Fischmeister, C.' ;CNRS-Universit\'e de Rennes 1 Rennes, France ; 'Griffin, S. T.' ;Department of Chemistry and Center for Green Manufacturing The University of Alabama Tuscaloosa, AL 35487 USA ; 'Rogers, R. D.' ;Department of Chemistry and Center for Green Manufacturing The University of Alabama Tuscaloosa, AL 35487 USA ; data_1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-methylimidazolium chloride hydrate ; _chemical_name_common ? _chemical_melting_point 137 _chemical_formula_moiety 'C15H27N2O, H2O, Cl' _chemical_formula_sum 'C15 H29 Cl N2 O2' _chemical_formula_weight 304.85 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2722(11) _cell_length_b 11.2447(16) _cell_length_c 37.776(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3513.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6025 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.55 _exptl_crystal_description Rectangular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7231 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details '(Sheldrick 2004, 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22770 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.37 _reflns_number_total 8353 _reflns_number_gt 6171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0316P)^2^+0.1776P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 3353 Friedel pairs' _refine_ls_abs_structure_Flack -0.01(4) _chemical_absolute_configuration syn _refine_ls_number_reflns 8353 _refine_ls_number_parameters 594 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.42922(7) 0.72498(5) 0.173489(16) 0.03594(15) Uani 1 1 d . . . O2 O 0.7760(3) 0.79865(16) 0.19917(6) 0.0442(5) Uani 1 1 d . . . H1W H 0.773(4) 0.806(3) 0.2209(9) 0.075(11) Uiso 1 1 d . . . H2W H 0.689(4) 0.790(3) 0.1935(8) 0.071(12) Uiso 1 1 d . . . O2' O 0.5364(2) 0.51342(18) 0.22503(4) 0.0383(4) Uani 1 1 d . . . H3W H 0.437(4) 0.467(3) 0.2225(8) 0.088(11) Uiso 1 1 d . . . H4W H 0.510(3) 0.568(2) 0.2149(7) 0.045(9) Uiso 1 1 d . . . O1 O 0.48344(17) 0.37984(12) 0.10770(4) 0.0261(3) Uani 1 1 d . . . N1 N 0.9152(2) 0.50148(15) 0.16321(4) 0.0286(4) Uani 1 1 d . . . N2 N 0.6827(2) 0.42683(15) 0.14990(4) 0.0233(4) Uani 1 1 d . . . C1 C 0.5375(3) 0.5114(2) 0.01748(7) 0.0378(6) Uani 1 1 d . . . H1B H 0.617(3) 0.5713(19) 0.0226(5) 0.027(6) Uiso 1 1 d . . . H1A H 0.565(3) 0.4737(19) -0.0058(7) 0.048(7) Uiso 1 1 d . . . C2 C 0.3332(3) 0.5388(2) 0.07955(7) 0.0310(5) Uani 1 1 d . . . H2B H 0.251(3) 0.4791(18) 0.0745(5) 0.026(5) Uiso 1 1 d . . . H2A H 0.312(2) 0.5736(18) 0.1022(6) 0.029(6) Uiso 1 1 d . . . C3 C 0.3299(3) 0.6322(2) 0.05035(6) 0.0345(6) Uani 1 1 d . . . H3 H 0.417(3) 0.6855(19) 0.0563(6) 0.036(6) Uiso 1 1 d . . . C4 C 0.3758(3) 0.5750(3) 0.01537(7) 0.0420(6) Uani 1 1 d . . . H4B H 0.303(3) 0.522(2) 0.0083(6) 0.036(7) Uiso 1 1 d . . . H4A H 0.374(2) 0.6368(19) -0.0032(6) 0.031(6) Uiso 1 1 d . . . C5 C 0.5425(3) 0.41732(19) 0.04659(5) 0.0263(5) Uani 1 1 d . . . H5 H 0.459(2) 0.3575(16) 0.0408(5) 0.016(5) Uiso 1 1 d . . . C6 C 0.4938(3) 0.47436(18) 0.08185(5) 0.0234(5) Uani 1 1 d . . . H6 H 0.577(2) 0.5314(15) 0.0895(4) 0.005(4) Uiso 1 1 d . . . C7 C 0.1685(4) 0.6957(3) 0.04860(10) 0.0517(8) Uani 1 1 d . . . H7C H 0.141(3) 0.731(2) 0.0711(7) 0.056(9) Uiso 1 1 d . . . H7B H 0.165(3) 0.760(2) 0.0308(7) 0.065(9) Uiso 1 1 d . . . H7A H 0.089(4) 0.637(3) 0.0396(8) 0.085(10) Uiso 1 1 d . . . C8 C 0.7039(3) 0.3495(2) 0.04887(6) 0.0326(5) Uani 1 1 d . . . H8 H 0.700(2) 0.3039(17) 0.0708(5) 0.023(5) Uiso 1 1 d . . . C9 C 0.9352(3) 0.3805(2) 0.15927(6) 0.0321(5) Uani 1 1 d . . . H9 H 1.031(3) 0.3453(19) 0.1624(5) 0.031(6) Uiso 1 1 d . . . C10 C 1.0424(3) 0.5876(3) 0.17205(9) 0.0441(6) Uani 1 1 d . . . H10G H 0.991(3) 0.662(3) 0.1812(7) 0.070(9) Uiso 1 1 d . . . H10H H 1.109(3) 0.551(2) 0.1906(8) 0.067(9) Uiso 1 1 d . . . H10I H 1.108(4) 0.603(2) 0.1530(8) 0.071(10) Uiso 1 1 d . . . C11 C 0.7914(3) 0.3350(2) 0.15096(5) 0.0285(5) Uani 1 1 d . . . H11 H 0.757(2) 0.2582(18) 0.1465(5) 0.026(6) Uiso 1 1 d . . . C12 C 0.7607(3) 0.5265(2) 0.15745(5) 0.0276(5) Uani 1 1 d . . . H12 H 0.715(3) 0.6004(19) 0.1586(5) 0.026(6) Uiso 1 1 d . . . C13 C 0.5081(3) 0.4165(2) 0.14254(6) 0.0263(5) Uani 1 1 d . . . H13E H 0.469(2) 0.3597(17) 0.1584(5) 0.018(5) Uiso 1 1 d . . . H13F H 0.452(2) 0.4963(18) 0.1477(5) 0.024(5) Uiso 1 1 d . . . C14 C 0.8507(3) 0.4301(3) 0.05195(9) 0.0500(7) Uani 1 1 d . . . H14G H 0.847(3) 0.485(2) 0.0713(7) 0.047(8) Uiso 1 1 d . . . H14H H 0.943(4) 0.382(2) 0.0560(7) 0.061(9) Uiso 1 1 d . . . H14I H 0.860(3) 0.470(2) 0.0302(8) 0.056(9) Uiso 1 1 d . . . C15 C 0.7240(4) 0.2629(3) 0.01798(8) 0.0531(8) Uani 1 1 d . . . H15G H 0.820(4) 0.216(3) 0.0207(8) 0.079(10) Uiso 1 1 d . . . H15H H 0.631(4) 0.206(3) 0.0145(8) 0.076(10) Uiso 1 1 d . . . H15I H 0.733(3) 0.303(2) -0.0041(7) 0.050(8) Uiso 1 1 d . . . O1' O 0.52315(18) 0.11322(11) 0.15992(3) 0.0281(3) Uani 1 1 d . . . N1' N 0.80086(19) 0.25802(14) 0.24156(4) 0.0239(4) Uani 1 1 d . . . N2' N 0.65760(18) 0.12911(14) 0.21361(4) 0.0212(4) Uani 1 1 d . . . C1' C 0.3807(3) -0.0167(2) 0.07405(6) 0.0331(6) Uani 1 1 d . . . H1C H 0.318(3) -0.080(2) 0.0819(5) 0.024(6) Uiso 1 1 d . . . H1D H 0.323(3) 0.0200(19) 0.0539(6) 0.033(6) Uiso 1 1 d . . . C2' C 0.6581(3) -0.0272(2) 0.12113(6) 0.0315(5) Uani 1 1 d . . . H2C H 0.718(2) 0.0385(17) 0.1120(5) 0.017(5) Uiso 1 1 d . . . H2D H 0.708(2) -0.0625(17) 0.1414(5) 0.024(6) Uiso 1 1 d . . . C3' C 0.6355(3) -0.1209(2) 0.09218(6) 0.0335(6) Uani 1 1 d . . . H3A H 0.572(2) -0.1795(18) 0.1027(5) 0.024(5) Uiso 1 1 d . . . C4' C 0.5432(3) -0.0644(2) 0.06170(6) 0.0342(6) Uani 1 1 d . . . H4C H 0.607(2) -0.0002(19) 0.0524(5) 0.023(5) Uiso 1 1 d . . . H4D H 0.533(2) -0.1230(18) 0.0433(6) 0.031(6) Uiso 1 1 d . . . C5' C 0.3960(3) 0.0745(2) 0.10401(5) 0.0258(5) Uani 1 1 d . . . H5A H 0.451(2) 0.1375(17) 0.0947(5) 0.014(5) Uiso 1 1 d . . . C6' C 0.4972(3) 0.02124(19) 0.13368(5) 0.0248(5) Uani 1 1 d . . . H6A H 0.447(2) -0.0380(16) 0.1437(5) 0.008(5) Uiso 1 1 d . . . C7' C 0.7949(4) -0.1745(3) 0.08104(9) 0.0537(8) Uani 1 1 d . . . H7D H 0.779(3) -0.235(2) 0.0622(7) 0.065(9) Uiso 1 1 d . . . H7E H 0.864(3) -0.108(2) 0.0715(6) 0.032(6) Uiso 1 1 d . . . H7F H 0.841(3) -0.207(2) 0.1003(7) 0.056(9) Uiso 1 1 d . . . C8' C 0.2332(3) 0.1231(2) 0.11759(6) 0.0344(5) Uani 1 1 d . . . H8A H 0.261(2) 0.1918(18) 0.1354(5) 0.028(5) Uiso 1 1 d . . . C9' C 0.9031(3) 0.1687(2) 0.23113(6) 0.0283(5) Uani 1 1 d . . . H9A H 1.017(3) 0.1720(19) 0.2353(6) 0.042(7) Uiso 1 1 d . . . C10' C 0.8465(3) 0.3650(2) 0.26159(7) 0.0350(6) Uani 1 1 d . . . H10D H 0.777(3) 0.428(2) 0.2563(6) 0.037(7) Uiso 1 1 d . . . H10E H 0.846(3) 0.342(2) 0.2855(8) 0.061(9) Uiso 1 1 d . . . H10F H 0.956(4) 0.390(2) 0.2545(7) 0.069(9) Uiso 1 1 d . . . C11' C 0.8134(3) 0.0879(2) 0.21362(6) 0.0270(5) Uani 1 1 d . . . H11A H 0.842(2) 0.0139(19) 0.2044(5) 0.026(6) Uiso 1 1 d . . . C12' C 0.6533(2) 0.2319(2) 0.23074(5) 0.0238(5) Uani 1 1 d . . . H12A H 0.564(2) 0.2774(16) 0.2342(5) 0.017(5) Uiso 1 1 d . . . C13' C 0.5190(3) 0.0754(2) 0.19533(5) 0.0259(5) Uani 1 1 d . . . H13C H 0.520(2) -0.0134(18) 0.1984(5) 0.018(5) Uiso 1 1 d . . . H13D H 0.418(3) 0.1003(17) 0.2075(5) 0.028(6) Uiso 1 1 d . . . C14' C 0.1298(4) 0.0316(3) 0.13653(9) 0.0565(8) Uani 1 1 d . . . H14D H 0.023(4) 0.079(3) 0.1443(8) 0.088(10) Uiso 1 1 d . . . H14E H 0.106(4) -0.029(3) 0.1204(10) 0.105(14) Uiso 1 1 d . . . H14F H 0.181(3) -0.001(2) 0.1568(7) 0.060(8) Uiso 1 1 d . . . C15' C 0.1372(4) 0.1818(3) 0.08799(8) 0.0463(7) Uani 1 1 d . . . H15D H 0.045(4) 0.224(3) 0.0984(8) 0.081(10) Uiso 1 1 d . . . H15E H 0.196(3) 0.237(2) 0.0749(7) 0.045(8) Uiso 1 1 d . . . H15F H 0.092(3) 0.122(2) 0.0706(7) 0.044(7) Uiso 1 1 d . . . Cl1 Cl 0.25557(6) 0.32650(5) 0.217618(15) 0.03698(15) 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 Cl1' 0.0359(3) 0.0277(3) 0.0443(3) 0.0050(3) -0.0008(3) -0.0015(3) O2 0.0427(13) 0.0437(11) 0.0462(13) -0.0073(9) -0.0010(9) -0.0028(9) O2' 0.0459(11) 0.0353(10) 0.0338(10) 0.0016(8) -0.0003(8) 0.0048(9) O1 0.0324(8) 0.0238(8) 0.0221(8) 0.0007(6) -0.0010(6) -0.0035(7) N1 0.0251(10) 0.0320(11) 0.0287(10) -0.0047(8) -0.0016(8) -0.0015(9) N2 0.0255(9) 0.0255(10) 0.0189(9) -0.0023(7) 0.0027(7) -0.0017(8) C1 0.0452(15) 0.0418(15) 0.0264(13) 0.0057(11) -0.0004(11) 0.0059(13) C2 0.0275(13) 0.0315(14) 0.0341(14) -0.0044(10) -0.0009(10) 0.0012(11) C3 0.0300(13) 0.0277(13) 0.0456(15) 0.0020(11) -0.0077(11) -0.0001(11) C4 0.0484(17) 0.0443(16) 0.0333(14) 0.0071(13) -0.0124(12) 0.0012(14) C5 0.0285(12) 0.0263(12) 0.0241(12) -0.0016(9) -0.0013(9) -0.0015(10) C6 0.0239(11) 0.0210(11) 0.0251(11) 0.0008(9) -0.0019(9) -0.0036(10) C7 0.0449(17) 0.0374(17) 0.073(2) 0.0041(16) -0.0137(16) 0.0055(14) C8 0.0343(13) 0.0338(14) 0.0295(13) 0.0032(10) 0.0039(10) 0.0058(10) C9 0.0299(13) 0.0334(13) 0.0329(13) -0.0001(10) -0.0030(10) 0.0070(12) C10 0.0350(15) 0.0442(17) 0.0531(18) -0.0110(15) -0.0004(14) -0.0103(13) C11 0.0337(13) 0.0259(13) 0.0260(12) 0.0009(10) -0.0013(9) 0.0014(11) C12 0.0311(12) 0.0246(12) 0.0270(12) -0.0034(9) 0.0034(10) 0.0002(11) C13 0.0238(11) 0.0324(13) 0.0229(12) -0.0001(10) 0.0030(9) -0.0028(11) C14 0.0323(16) 0.059(2) 0.058(2) 0.0029(17) 0.0013(14) 0.0061(15) C15 0.063(2) 0.0544(19) 0.0417(17) -0.0068(15) 0.0093(15) 0.0194(18) O1' 0.0419(9) 0.0223(8) 0.0202(8) 0.0008(6) -0.0056(7) -0.0043(7) N1' 0.0223(9) 0.0242(10) 0.0252(9) -0.0023(7) -0.0009(7) -0.0009(8) N2' 0.0198(9) 0.0251(9) 0.0186(9) 0.0014(7) 0.0006(7) -0.0013(7) C1' 0.0383(14) 0.0353(14) 0.0257(13) -0.0041(11) -0.0046(10) -0.0040(12) C2' 0.0333(13) 0.0330(14) 0.0281(13) 0.0052(11) 0.0008(10) -0.0003(12) C3' 0.0408(14) 0.0299(14) 0.0298(13) 0.0015(10) 0.0066(11) 0.0010(12) C4' 0.0490(16) 0.0273(13) 0.0263(13) -0.0025(10) 0.0061(11) -0.0033(12) C5' 0.0294(12) 0.0260(12) 0.0222(11) 0.0020(10) -0.0017(9) -0.0053(10) C6' 0.0294(12) 0.0216(11) 0.0235(11) 0.0014(9) 0.0017(9) -0.0074(10) C7' 0.0585(19) 0.060(2) 0.0421(18) -0.0008(17) 0.0095(15) 0.0218(18) C8' 0.0311(13) 0.0431(14) 0.0291(12) -0.0037(11) -0.0039(10) 0.0006(12) C9' 0.0212(11) 0.0300(12) 0.0336(13) 0.0037(10) -0.0015(9) 0.0022(11) C10' 0.0308(14) 0.0327(15) 0.0413(16) -0.0102(12) -0.0064(12) -0.0045(12) C11' 0.0260(11) 0.0250(12) 0.0299(12) -0.0026(10) 0.0011(9) 0.0057(10) C12' 0.0195(11) 0.0298(13) 0.0223(11) -0.0023(9) 0.0007(8) 0.0019(10) C13' 0.0266(12) 0.0282(13) 0.0230(11) -0.0003(9) 0.0016(9) -0.0044(10) C14' 0.0342(15) 0.085(3) 0.050(2) 0.0153(19) 0.0050(14) -0.0028(17) C15' 0.0407(15) 0.0541(19) 0.0441(17) 0.0035(15) -0.0038(13) 0.0149(16) Cl1 0.0239(3) 0.0465(3) 0.0406(3) 0.0057(3) 0.0010(3) 0.0006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.394(2) . ? O1 C6 1.446(2) . ? N1 C12 1.326(3) . ? N1 C9 1.378(3) . ? N1 C10 1.469(3) . ? N2 C12 1.324(3) . ? N2 C11 1.370(3) . ? N2 C13 1.475(3) . ? C1 C4 1.519(3) . ? C1 C5 1.526(3) . ? C2 C6 1.516(3) . ? C2 C3 1.524(3) . ? C3 C7 1.516(4) . ? C3 C4 1.518(4) . ? C5 C6 1.532(3) . ? C5 C8 1.540(3) . ? C8 C14 1.520(4) . ? C8 C15 1.529(4) . ? C9 C11 1.333(3) . ? O1' C13' 1.404(2) . ? O1' C6' 1.449(2) . ? N1' C12' 1.320(2) . ? N1' C9' 1.371(3) . ? N1' C10' 1.471(3) . ? N2' C12' 1.325(3) . ? N2' C11' 1.369(3) . ? N2' C13' 1.468(3) . ? C1' C4' 1.521(3) . ? C1' C5' 1.532(3) . ? C2' C6' 1.514(3) . ? C2' C3' 1.530(3) . ? C3' C7' 1.510(4) . ? C3' C4' 1.520(3) . ? C5' C6' 1.522(3) . ? C5' C8' 1.541(3) . ? C8' C14' 1.517(4) . ? C8' C15' 1.523(3) . ? C9' C11' 1.346(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 C13 O1 C6 114.30(16) . . ? C12 N1 C9 107.91(19) . . ? C12 N1 C10 126.0(2) . . ? C9 N1 C10 126.1(2) . . ? C12 N2 C11 108.19(18) . . ? C12 N2 C13 125.74(19) . . ? C11 N2 C13 126.05(19) . . ? C4 C1 C5 112.8(2) . . ? C6 C2 C3 112.74(19) . . ? C7 C3 C4 112.5(2) . . ? C7 C3 C2 111.9(2) . . ? C4 C3 C2 109.5(2) . . ? C3 C4 C1 112.0(2) . . ? C1 C5 C6 109.22(18) . . ? C1 C5 C8 114.01(18) . . ? C6 C5 C8 112.72(17) . . ? O1 C6 C2 109.73(17) . . ? O1 C6 C5 107.17(16) . . ? C2 C6 C5 112.36(18) . . ? C14 C8 C15 110.6(2) . . ? C14 C8 C5 113.7(2) . . ? C15 C8 C5 111.5(2) . . ? C11 C9 N1 107.3(2) . . ? C9 C11 N2 107.6(2) . . ? N2 C12 N1 109.0(2) . . ? O1 C13 N2 110.16(16) . . ? C13' O1' C6' 115.59(16) . . ? C12' N1' C9' 108.56(17) . . ? C12' N1' C10' 125.36(18) . . ? C9' N1' C10' 126.08(18) . . ? C12' N2' C11' 108.66(17) . . ? C12' N2' C13' 124.60(18) . . ? C11' N2' C13' 126.55(17) . . ? C4' C1' C5' 112.94(19) . . ? C6' C2' C3' 111.36(19) . . ? C7' C3' C4' 113.2(2) . . ? C7' C3' C2' 111.5(2) . . ? C4' C3' C2' 108.39(19) . . ? C3' C4' C1' 111.03(19) . . ? C6' C5' C1' 109.01(19) . . ? C6' C5' C8' 112.01(17) . . ? C1' C5' C8' 114.24(18) . . ? O1' C6' C2' 109.93(17) . . ? O1' C6' C5' 107.72(16) . . ? C2' C6' C5' 113.23(18) . . ? C14' C8' C15' 110.3(2) . . ? C14' C8' C5' 114.2(2) . . ? C15' C8' C5' 111.4(2) . . ? C11' C9' N1' 107.17(18) . . ? C9' C11' N2' 106.92(19) . . ? N1' C12' N2' 108.69(19) . . ? O1' C13' N2' 107.72(16) . . ? 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 N2 C13 O1 C6 -81.2(2) . . . . ? N2' C13' O1' C6' 134.30(17) . . . . ? 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 O2' H3W Cl1 0.98(3) 2.19(3) 3.145(2) 166(3) . O2 H1W Cl1 0.83(3) 2.34(3) 3.170(2) 176(3) 3_655 O2 H2W Cl1' 0.76(3) 2.39(3) 3.140(2) 170(3) . O2' H4W Cl1' 0.76(3) 2.45(3) 3.200(2) 171(3) . C10 H10G O2 1.01(3) 2.44(3) 3.397(4) 158(2) . C12' H12A Cl1 0.911(19) 2.681(19) 3.493(2) 149.1(15) . C9' H9A Cl1 0.96(2) 2.71(2) 3.451(2) 134.6(17) 1_655 C11' H11A O2 0.93(2) 2.49(2) 3.313(3) 147.2(17) 1_545 C10' H10D O2' 0.93(2) 2.51(2) 3.358(3) 151.4(18) . C13 H13F Cl1' 1.03(2) 2.76(2) 3.718(2) 155.8(15) . C9 H9 Cl1 0.90(2) 2.80(2) 3.500(3) 135.9(17) 1_655 C12 H12 Cl1' 0.91(2) 2.81(2) 3.587(2) 144.3(16) . C11 H11 O1' 0.92(2) 2.58(2) 3.355(3) 141.6(16) . _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.327 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.041 data_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-[(1R,2S,5R)--(--)--menthoxymethyl]-3-ethylimidazolium chloride hemihydrate ; _chemical_name_common ; ? ; _chemical_melting_point 144 _chemical_formula_moiety 'C16H29N2O, 0.5 H2O, Cl' _chemical_formula_sum 'C16 H30 Cl N2 O1.50' _chemical_formula_weight 309.87 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 P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.0143(14) _cell_length_b 8.0671(8) _cell_length_c 17.9287(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.636(2) _cell_angle_gamma 90.00 _cell_volume 1829.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3386 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 23.53 _exptl_crystal_description Rectangular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7468 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details '(Sheldrick 2004, 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11927 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 28.26 _reflns_number_total 7007 _reflns_number_gt 4228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0963P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0030(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2421 Friedel pairs' _refine_ls_abs_structure_Flack 0.22(7) _chemical_absolute_configuration syn _refine_ls_number_reflns 7007 _refine_ls_number_parameters 371 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1668 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 Cl1 Cl -0.15422(8) 0.20680(16) -0.38585(5) 0.0672(3) Uani 1 1 d . . . Cl2 Cl -0.62380(8) 1.01606(13) -0.37404(6) 0.0672(3) Uani 1 1 d . . . O1 O -0.33956(16) 0.2349(3) -0.22120(12) 0.0459(5) Uani 1 1 d . . . O1' O 0.16436(16) -0.7773(3) -0.23172(12) 0.0430(5) Uani 1 1 d . . . O2 O -0.1819(3) 0.5116(5) -0.4917(2) 0.1262(16) Uani 1 1 d . . . N1 N -0.4107(5) 0.6276(6) -0.3861(3) 0.1056(17) Uani 1 1 d . . . N1' N 0.0849(3) -0.4364(4) -0.40933(18) 0.0610(9) Uani 1 1 d . . . N2 N -0.4124(2) 0.3913(4) -0.33153(17) 0.0555(8) Uani 1 1 d . . . N2' N 0.1335(2) -0.6737(3) -0.35806(15) 0.0438(7) Uani 1 1 d . . . C1 C -0.0918(3) 0.4118(5) -0.0966(2) 0.0501(9) Uani 1 1 d . . . H1B H -0.0681 0.4801 -0.1353 0.060 Uiso 1 1 calc R . . H1C H -0.0788 0.4761 -0.0483 0.060 Uiso 1 1 calc R . . C1' C 0.4075(3) -0.5989(5) -0.1014(2) 0.0499(9) Uani 1 1 d . . . H1'A H 0.4349 -0.5363 -0.1401 0.060 Uiso 1 1 calc R . . H1'B H 0.4176 -0.5295 -0.0547 0.060 Uiso 1 1 calc R . . C2 C -0.1647(3) 0.1158(4) -0.1841(2) 0.0417(8) Uani 1 1 d . . . H2A H -0.1773 0.0529 -0.2328 0.050 Uiso 1 1 calc R . . H2B H -0.1898 0.0473 -0.1461 0.050 Uiso 1 1 calc R . . C2' C 0.3348(3) -0.9062(4) -0.1808(2) 0.0443(8) Uani 1 1 d . . . H2'A H 0.3236 -0.9785 -0.2266 0.053 Uiso 1 1 calc R . . H2'B H 0.3064 -0.9640 -0.1412 0.053 Uiso 1 1 calc R . . C3 C -0.0462(3) 0.1465(4) -0.1551(2) 0.0455(8) Uani 1 1 d . . . H3A H -0.0211 0.2090 -0.1956 0.055 Uiso 1 1 calc R . . C3' C 0.4534(3) -0.8752(4) -0.1500(2) 0.0455(8) Uani 1 1 d . . . H3'A H 0.4799 -0.8188 -0.1915 0.055 Uiso 1 1 calc R . . C4 C -0.0268(3) 0.2537(5) -0.0830(2) 0.0511(9) Uani 1 1 d . . . H4A H -0.0453 0.1901 -0.0408 0.061 Uiso 1 1 calc R . . H4B H 0.0492 0.2824 -0.0671 0.061 Uiso 1 1 calc R . . C4' C 0.4705(3) -0.7576(5) -0.08202(19) 0.0497(9) Uani 1 1 d . . . H4'A H 0.4494 -0.8135 -0.0388 0.060 Uiso 1 1 calc R . . H4'B H 0.5466 -0.7302 -0.0653 0.060 Uiso 1 1 calc R . . C5 C -0.2105(2) 0.3789(4) -0.12431(18) 0.0411(8) Uani 1 1 d . . . H5A H -0.2315 0.3085 -0.0845 0.049 Uiso 1 1 calc R . . C5' C 0.2893(3) -0.6308(4) -0.13270(19) 0.0436(8) Uani 1 1 d . . . H5'A H 0.2646 -0.6942 -0.0922 0.052 Uiso 1 1 calc R . . C6 C -0.2275(2) 0.2751(4) -0.19720(18) 0.0381(7) Uani 1 1 d . . . H6A H -0.2062 0.3409 -0.2384 0.046 Uiso 1 1 calc R . . C6' C 0.2763(2) -0.7452(4) -0.20175(18) 0.0390(7) Uani 1 1 d . . . H6'A H 0.3048 -0.6885 -0.2422 0.047 Uiso 1 1 calc R . . C7 C 0.0145(3) -0.0152(5) -0.1407(2) 0.0589(10) Uani 1 1 d . . . H7A H 0.0902 0.0082 -0.1231 0.088 Uiso 1 1 calc R . . H7B H 0.0017 -0.0796 -0.1883 0.088 Uiso 1 1 calc R . . H7C H -0.0093 -0.0787 -0.1013 0.088 Uiso 1 1 calc R . . C7' C 0.5142(3) -1.0389(5) -0.1316(2) 0.0590(10) Uani 1 1 d . . . H7'A H 0.5896 -1.0155 -0.1122 0.088 Uiso 1 1 calc R . . H7'B H 0.5039 -1.1062 -0.1782 0.088 Uiso 1 1 calc R . . H7'C H 0.4878 -1.0994 -0.0925 0.088 Uiso 1 1 calc R . . C8 C -0.2797(3) 0.5358(5) -0.1335(2) 0.0516(9) Uani 1 1 d . . . H8A H -0.3538 0.5015 -0.1578 0.062 Uiso 1 1 calc R . . C8' C 0.2211(3) -0.4729(5) -0.1486(2) 0.0530(9) Uani 1 1 d . . . H8'A H 0.1467 -0.5088 -0.1708 0.064 Uiso 1 1 calc R . . C9 C -0.4931(5) 0.6314(7) -0.3513(3) 0.0963(19) Uani 1 1 d . . . H9A H -0.5396 0.7219 -0.3507 0.116 Uiso 1 1 calc R . . C9' C 0.1744(3) -0.4849(6) -0.4326(2) 0.0649(11) Uani 1 1 d . . . H9'A H 0.2082 -0.4245 -0.4656 0.078 Uiso 1 1 calc R . . C10 C -0.3452(7) 0.8015(11) -0.4167(4) 0.143(3) Uani 1 1 d . . . H10A H -0.3338 0.8951 -0.3799 0.171 Uiso 1 1 calc R . . H10B H -0.2788 0.7720 -0.4314 0.171 Uiso 1 1 calc R . . C10' C 0.0255(4) -0.2798(7) -0.4306(3) 0.0949(17) Uani 1 1 d . . . H10C H -0.0302 -0.2974 -0.4781 0.114 Uiso 1 1 calc R . . H10D H 0.0742 -0.1933 -0.4411 0.114 Uiso 1 1 calc R . . C11 C -0.4962(3) 0.4791(6) -0.3172(2) 0.0677(12) Uani 1 1 d . . . H11A H -0.5458 0.4424 -0.2896 0.081 Uiso 1 1 calc R . . C11' C 0.2045(3) -0.6302(5) -0.40088(19) 0.0561(10) Uani 1 1 d . . . H11B H 0.2640 -0.6930 -0.4065 0.067 Uiso 1 1 calc R . . C12 C -0.3623(4) 0.4849(6) -0.3734(3) 0.0793(14) Uani 1 1 d . . . H12A H -0.3018 0.4530 -0.3909 0.095 Uiso 1 1 calc R . . C12' C 0.0611(3) -0.5541(5) -0.3662(2) 0.0591(10) Uani 1 1 d . . . H12B H 0.0015 -0.5544 -0.3442 0.071 Uiso 1 1 calc R . . C13 C -0.3787(3) 0.2266(5) -0.29999(19) 0.0487(8) Uani 1 1 d . . . H13A H -0.4396 0.1494 -0.3119 0.058 Uiso 1 1 calc R . . H13B H -0.3233 0.1830 -0.3242 0.058 Uiso 1 1 calc R . . C13' C 0.1361(3) -0.8206(4) -0.3087(2) 0.0487(9) Uani 1 1 d . . . H13C H 0.0655 -0.8737 -0.3203 0.058 Uiso 1 1 calc R . . H13D H 0.1876 -0.9018 -0.3198 0.058 Uiso 1 1 calc R . . C14 C -0.2477(4) 0.6679(5) -0.1855(3) 0.0659(11) Uani 1 1 d . . . H14A H -0.2483 0.6190 -0.2357 0.099 Uiso 1 1 calc R . . H14B H -0.1765 0.7085 -0.1619 0.099 Uiso 1 1 calc R . . H14C H -0.2979 0.7603 -0.1922 0.099 Uiso 1 1 calc R . . C14' C 0.2526(4) -0.3578(5) -0.2071(2) 0.0694(12) Uani 1 1 d . . . H14D H 0.2067 -0.2599 -0.2148 0.104 Uiso 1 1 calc R . . H14E H 0.2451 -0.4164 -0.2559 0.104 Uiso 1 1 calc R . . H14F H 0.3263 -0.3231 -0.1880 0.104 Uiso 1 1 calc R . . C15 C -0.2797(4) 0.6102(6) -0.0554(2) 0.0772(14) Uani 1 1 d . . . H15A H -0.3235 0.7103 -0.0624 0.116 Uiso 1 1 calc R . . H15B H -0.2072 0.6388 -0.0287 0.116 Uiso 1 1 calc R . . H15C H -0.3084 0.5293 -0.0249 0.116 Uiso 1 1 calc R . . C15' C 0.2218(4) -0.3783(6) -0.0740(3) 0.0827(15) Uani 1 1 d . . . H15D H 0.1778 -0.2789 -0.0859 0.124 Uiso 1 1 calc R . . H15E H 0.2945 -0.3460 -0.0493 0.124 Uiso 1 1 calc R . . H15F H 0.1938 -0.4498 -0.0393 0.124 Uiso 1 1 calc R . . C16 C -0.4257(7) 0.823(2) -0.4753(6) 0.254(9) Uani 1 1 d . . . H16A H -0.4117 0.9169 -0.5060 0.382 Uiso 1 1 calc R . . H16B H -0.4895 0.8448 -0.4569 0.382 Uiso 1 1 calc R . . H16C H -0.4361 0.7224 -0.5071 0.382 Uiso 1 1 calc R . . C16' C -0.0264(6) -0.2193(8) -0.3657(4) 0.138(3) Uani 1 1 d . . . H16D H -0.0649 -0.1159 -0.3815 0.207 Uiso 1 1 calc R . . H16E H 0.0287 -0.2000 -0.3188 0.207 Uiso 1 1 calc R . . H16F H -0.0756 -0.3039 -0.3558 0.207 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 0.0588(6) 0.0928(8) 0.0479(5) -0.0026(5) 0.0082(4) 0.0228(6) Cl2 0.0556(6) 0.0654(6) 0.0722(6) -0.0122(5) -0.0015(5) 0.0122(5) O1 0.0351(11) 0.0489(14) 0.0510(12) -0.0031(11) 0.0049(10) -0.0034(11) O1' 0.0345(11) 0.0438(13) 0.0461(12) 0.0075(11) 0.0003(9) -0.0023(11) O2 0.115(3) 0.083(2) 0.138(3) 0.004(2) -0.056(2) 0.004(2) N1 0.166(5) 0.077(3) 0.092(3) 0.043(2) 0.067(3) 0.057(3) N1' 0.059(2) 0.053(2) 0.0629(19) 0.0198(17) -0.0032(16) 0.0056(16) N2 0.0536(18) 0.0542(19) 0.0518(17) -0.0008(16) -0.0014(15) 0.0144(16) N2' 0.0434(16) 0.0398(15) 0.0433(15) 0.0029(13) 0.0002(13) 0.0063(13) C1 0.0461(19) 0.045(2) 0.0531(19) -0.0039(17) -0.0001(16) 0.0059(17) C1' 0.0445(19) 0.045(2) 0.053(2) -0.0025(17) -0.0033(16) 0.0023(17) C2 0.0460(19) 0.0334(17) 0.0457(18) -0.0037(14) 0.0106(15) 0.0014(14) C2' 0.048(2) 0.0359(18) 0.0452(18) 0.0033(15) 0.0039(15) 0.0045(15) C3 0.0373(18) 0.047(2) 0.0526(19) 0.0064(16) 0.0113(15) 0.0089(15) C3' 0.0390(19) 0.048(2) 0.0476(19) 0.0051(16) 0.0068(15) 0.0075(16) C4 0.0342(17) 0.056(2) 0.057(2) 0.0004(18) -0.0011(15) 0.0052(16) C4' 0.0383(17) 0.052(2) 0.0514(19) 0.0032(17) -0.0034(15) 0.0056(17) C5 0.0390(18) 0.0414(19) 0.0413(17) -0.0029(15) 0.0059(14) 0.0031(15) C5' 0.0428(19) 0.0410(19) 0.0438(18) 0.0043(16) 0.0037(15) 0.0037(15) C6 0.0307(16) 0.0357(18) 0.0458(17) 0.0016(14) 0.0048(14) 0.0003(13) C6' 0.0348(16) 0.0400(19) 0.0392(16) 0.0061(14) 0.0025(13) -0.0011(14) C7 0.051(2) 0.059(3) 0.066(2) 0.005(2) 0.0112(18) 0.0206(19) C7' 0.049(2) 0.049(2) 0.074(2) -0.003(2) 0.0049(19) 0.0117(17) C8 0.053(2) 0.044(2) 0.053(2) -0.0072(18) 0.0019(16) 0.0127(17) C8' 0.053(2) 0.0426(19) 0.055(2) -0.0043(18) -0.0041(17) 0.0110(18) C9 0.130(5) 0.096(4) 0.061(3) 0.010(3) 0.019(3) 0.069(4) C9' 0.074(3) 0.073(3) 0.047(2) 0.013(2) 0.0125(19) 0.005(2) C10 0.178(8) 0.164(7) 0.089(4) 0.026(5) 0.039(5) 0.059(6) C10' 0.083(3) 0.079(3) 0.120(4) 0.051(4) 0.020(3) 0.037(3) C11 0.058(2) 0.080(3) 0.064(2) 0.009(2) 0.0127(19) 0.024(2) C11' 0.062(2) 0.065(3) 0.0425(19) -0.0041(19) 0.0146(18) 0.006(2) C12 0.102(4) 0.072(3) 0.074(3) 0.018(3) 0.040(3) 0.030(3) C12' 0.054(2) 0.052(2) 0.067(2) 0.009(2) 0.0053(19) 0.0085(19) C13 0.0398(18) 0.050(2) 0.0506(19) -0.0045(18) 0.0002(15) 0.0030(17) C13' 0.0427(18) 0.0396(19) 0.058(2) -0.0017(17) -0.0006(16) -0.0017(15) C14 0.074(3) 0.034(2) 0.087(3) 0.004(2) 0.014(2) 0.0080(18) C14' 0.079(3) 0.038(2) 0.077(3) 0.008(2) -0.011(2) 0.0002(19) C15 0.084(3) 0.070(3) 0.070(3) -0.019(2) 0.003(2) 0.025(3) C15' 0.091(4) 0.070(3) 0.077(3) -0.018(2) 0.000(3) 0.036(3) C16 0.146(8) 0.45(3) 0.174(9) -0.131(13) 0.046(7) 0.075(11) C16' 0.159(7) 0.082(4) 0.135(5) -0.010(4) -0.043(5) 0.054(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.386(4) . ? O1 C6 1.457(4) . ? O1' C13' 1.387(4) . ? O1' C6' 1.452(4) . ? N1 C12 1.306(6) . ? N1 C9 1.362(8) . ? N1 C10 1.793(10) . ? N1' C12' 1.307(5) . ? N1' C9' 1.383(6) . ? N1' C10' 1.484(6) . ? N2 C12 1.337(6) . ? N2 C11 1.374(5) . ? N2 C13 1.470(5) . ? N2' C12' 1.332(5) . ? N2' C11' 1.379(5) . ? N2' C13' 1.475(4) . ? C1 C4 1.518(5) . ? C1 C5 1.530(5) . ? C1 H1B 0.9900 . ? C1 H1C 0.9900 . ? C1' C4' 1.516(5) . ? C1' C5' 1.530(5) . ? C1' H1'A 0.9900 . ? C1' H1'B 0.9900 . ? C2 C6 1.512(4) . ? C2 C3 1.526(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2' C6' 1.507(5) . ? C2' C3' 1.532(5) . ? C2' H2'A 0.9900 . ? C2' H2'B 0.9900 . ? C3 C7 1.515(5) . ? C3 C4 1.526(5) . ? C3 H3A 1.0000 . ? C3' C4' 1.519(5) . ? C3' C7' 1.534(5) . ? C3' H3'A 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4' H4'A 0.9900 . ? C4' H4'B 0.9900 . ? C5 C6 1.524(5) . ? C5 C8 1.539(5) . ? C5 H5A 1.0000 . ? C5' C6' 1.521(5) . ? C5' C8' 1.540(5) . ? C5' H5'A 1.0000 . ? C6 H6A 1.0000 . ? C6' H6'A 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7' H7'A 0.9800 . ? C7' H7'B 0.9800 . ? C7' H7'C 0.9800 . ? C8 C15 1.523(5) . ? C8 C14 1.537(6) . ? C8 H8A 1.0000 . ? C8' C14' 1.527(6) . ? C8' C15' 1.538(6) . ? C8' H8'A 1.0000 . ? C9 C11 1.377(7) . ? C9 H9A 0.9500 . ? C9' C11' 1.322(6) . ? C9' H9'A 0.9500 . ? C10 C16 1.309(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10' C16' 1.555(9) . ? C10' H10C 0.9900 . ? C10' H10D 0.9900 . ? C11 H11A 0.9500 . ? C11' H11B 0.9500 . ? C12 H12A 0.9500 . ? C12' H12B 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14' H14D 0.9800 . ? C14' H14E 0.9800 . ? C14' H14F 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16' H16D 0.9800 . ? C16' H16E 0.9800 . ? C16' H16F 0.9800 . ? 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 C13 O1 C6 114.4(2) . . ? C13' O1' C6' 114.9(2) . . ? C12 N1 C9 109.8(5) . . ? C12 N1 C10 119.9(5) . . ? C9 N1 C10 127.2(5) . . ? C12' N1' C9' 107.9(3) . . ? C12' N1' C10' 126.0(4) . . ? C9' N1' C10' 126.0(4) . . ? C12 N2 C11 109.1(4) . . ? C12 N2 C13 125.9(3) . . ? C11 N2 C13 124.9(3) . . ? C12' N2' C11' 107.7(3) . . ? C12' N2' C13' 124.3(3) . . ? C11' N2' C13' 127.9(3) . . ? C4 C1 C5 112.9(3) . . ? C4 C1 H1B 109.0 . . ? C5 C1 H1B 109.0 . . ? C4 C1 H1C 109.0 . . ? C5 C1 H1C 109.0 . . ? H1B C1 H1C 107.8 . . ? C4' C1' C5' 112.6(3) . . ? C4' C1' H1'A 109.1 . . ? C5' C1' H1'A 109.1 . . ? C4' C1' H1'B 109.1 . . ? C5' C1' H1'B 109.1 . . ? H1'A C1' H1'B 107.8 . . ? C6 C2 C3 112.4(3) . . ? C6 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C6 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C6' C2' C3' 110.9(3) . . ? C6' C2' H2'A 109.5 . . ? C3' C2' H2'A 109.5 . . ? C6' C2' H2'B 109.5 . . ? C3' C2' H2'B 109.5 . . ? H2'A C2' H2'B 108.1 . . ? C7 C3 C4 111.6(3) . . ? C7 C3 C2 111.3(3) . . ? C4 C3 C2 109.4(3) . . ? C7 C3 H3A 108.2 . . ? C4 C3 H3A 108.2 . . ? C2 C3 H3A 108.2 . . ? C4' C3' C2' 109.6(3) . . ? C4' C3' C7' 113.2(3) . . ? C2' C3' C7' 111.2(3) . . ? C4' C3' H3'A 107.5 . . ? C2' C3' H3'A 107.5 . . ? C7' C3' H3'A 107.5 . . ? C1 C4 C3 111.4(3) . . ? C1 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C1 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C1' C4' C3' 112.0(3) . . ? C1' C4' H4'A 109.2 . . ? C3' C4' H4'A 109.2 . . ? C1' C4' H4'B 109.2 . . ? C3' C4' H4'B 109.2 . . ? H4'A C4' H4'B 107.9 . . ? C6 C5 C1 107.8(3) . . ? C6 C5 C8 113.4(3) . . ? C1 C5 C8 114.4(3) . . ? C6 C5 H5A 107.0 . . ? C1 C5 H5A 107.0 . . ? C8 C5 H5A 107.0 . . ? C6' C5' C1' 108.0(3) . . ? C6' C5' C8' 113.7(3) . . ? C1' C5' C8' 114.4(3) . . ? C6' C5' H5'A 106.7 . . ? C1' C5' H5'A 106.7 . . ? C8' C5' H5'A 106.7 . . ? O1 C6 C2 108.9(3) . . ? O1 C6 C5 108.0(2) . . ? C2 C6 C5 111.7(3) . . ? O1 C6 H6A 109.4 . . ? C2 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O1' C6' C2' 110.0(3) . . ? O1' C6' C5' 108.6(3) . . ? C2' C6' C5' 111.5(3) . . ? O1' C6' H6'A 108.9 . . ? C2' C6' H6'A 108.9 . . ? C5' C6' H6'A 108.9 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3' C7' H7'A 109.5 . . ? C3' C7' H7'B 109.5 . . ? H7'A C7' H7'B 109.5 . . ? C3' C7' H7'C 109.5 . . ? H7'A C7' H7'C 109.5 . . ? H7'B C7' H7'C 109.5 . . ? C15 C8 C14 110.1(4) . . ? C15 C8 C5 110.7(3) . . ? C14 C8 C5 113.6(3) . . ? C15 C8 H8A 107.4 . . ? C14 C8 H8A 107.4 . . ? C5 C8 H8A 107.4 . . ? C14' C8' C15' 110.3(4) . . ? C14' C8' C5' 113.2(3) . . ? C15' C8' C5' 111.4(3) . . ? C14' C8' H8'A 107.2 . . ? C15' C8' H8'A 107.2 . . ? C5' C8' H8'A 107.2 . . ? N1 C9 C11 107.0(4) . . ? N1 C9 H9A 126.5 . . ? C11 C9 H9A 126.5 . . ? C11' C9' N1' 107.8(4) . . ? C11' C9' H9'A 126.1 . . ? N1' C9' H9'A 126.1 . . ? C16 C10 N1 90.0(10) . . ? C16 C10 H10A 113.6 . . ? N1 C10 H10A 113.6 . . ? C16 C10 H10B 113.6 . . ? N1 C10 H10B 113.6 . . ? H10A C10 H10B 110.9 . . ? N1' C10' C16' 111.5(4) . . ? N1' C10' H10C 109.3 . . ? C16' C10' H10C 109.3 . . ? N1' C10' H10D 109.3 . . ? C16' C10' H10D 109.3 . . ? H10C C10' H10D 108.0 . . ? N2 C11 C9 105.6(4) . . ? N2 C11 H11A 127.2 . . ? C9 C11 H11A 127.2 . . ? C9' C11' N2' 107.2(4) . . ? C9' C11' H11B 126.4 . . ? N2' C11' H11B 126.4 . . ? N1 C12 N2 108.5(5) . . ? N1 C12 H12A 125.7 . . ? N2 C12 H12A 125.7 . . ? N1' C12' N2' 109.3(4) . . ? N1' C12' H12B 125.3 . . ? N2' C12' H12B 125.3 . . ? O1 C13 N2 110.7(3) . . ? O1 C13 H13A 109.5 . . ? N2 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O1' C13' N2' 111.0(3) . . ? O1' C13' H13C 109.4 . . ? N2' C13' H13C 109.4 . . ? O1' C13' H13D 109.4 . . ? N2' C13' H13D 109.4 . . ? H13C C13' H13D 108.0 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8' C14' H14D 109.5 . . ? C8' C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? C8' C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8' C15' H15D 109.5 . . ? C8' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C8' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C10' C16' H16D 109.5 . . ? C10' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? C10' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C2 C3 C7 178.6(3) . . . . ? C6 C2 C3 C4 54.9(4) . . . . ? C6' C2' C3' C4' 56.4(4) . . . . ? C6' C2' C3' C7' -177.7(3) . . . . ? C5 C1 C4 C3 56.9(4) . . . . ? C7 C3 C4 C1 -177.2(3) . . . . ? C2 C3 C4 C1 -53.7(4) . . . . ? C5' C1' C4' C3' 55.3(4) . . . . ? C2' C3' C4' C1' -53.9(4) . . . . ? C7' C3' C4' C1' -178.6(3) . . . . ? C4 C1 C5 C6 -56.9(4) . . . . ? C4 C1 C5 C8 176.1(3) . . . . ? C4' C1' C5' C6' -55.7(4) . . . . ? C4' C1' C5' C8' 176.5(3) . . . . ? C13 O1 C6 C2 -92.6(3) . . . . ? C13 O1 C6 C5 145.9(3) . . . . ? C3 C2 C6 O1 -177.4(3) . . . . ? C3 C2 C6 C5 -58.2(4) . . . . ? C1 C5 C6 O1 176.6(3) . . . . ? C8 C5 C6 O1 -55.8(4) . . . . ? C1 C5 C6 C2 56.9(4) . . . . ? C8 C5 C6 C2 -175.5(3) . . . . ? C13' O1' C6' C2' -82.4(3) . . . . ? C13' O1' C6' C5' 155.3(3) . . . . ? C3' C2' C6' O1' 179.2(3) . . . . ? C3' C2' C6' C5' -60.3(4) . . . . ? C1' C5' C6' O1' 179.7(3) . . . . ? C8' C5' C6' O1' -52.1(4) . . . . ? C1' C5' C6' C2' 58.3(4) . . . . ? C8' C5' C6' C2' -173.5(3) . . . . ? C6 C5 C8 C15 166.0(3) . . . . ? C1 C5 C8 C15 -69.9(4) . . . . ? C6 C5 C8 C14 -69.6(4) . . . . ? C1 C5 C8 C14 54.5(4) . . . . ? C6' C5' C8' C14' -65.3(4) . . . . ? C1' C5' C8' C14' 59.6(4) . . . . ? C6' C5' C8' C15' 169.7(3) . . . . ? C1' C5' C8' C15' -65.4(5) . . . . ? C12 N1 C9 C11 -1.7(7) . . . . ? C10 N1 C9 C11 -161.6(5) . . . . ? C12' N1' C9' C11' -1.8(5) . . . . ? C10' N1' C9' C11' 179.2(4) . . . . ? C12 N1 C10 C16 126.6(7) . . . . ? C9 N1 C10 C16 -75.3(8) . . . . ? C12' N1' C10' C16' 32.3(7) . . . . ? C9' N1' C10' C16' -148.9(5) . . . . ? C12 N2 C11 C9 -1.0(5) . . . . ? C13 N2 C11 C9 174.2(4) . . . . ? N1 C9 C11 N2 1.7(6) . . . . ? N1' C9' C11' N2' 0.5(4) . . . . ? C12' N2' C11' C9' 1.0(4) . . . . ? C13' N2' C11' C9' -176.6(3) . . . . ? C9 N1 C12 N2 1.1(7) . . . . ? C10 N1 C12 N2 162.7(4) . . . . ? C11 N2 C12 N1 0.0(6) . . . . ? C13 N2 C12 N1 -175.2(4) . . . . ? C9' N1' C12' N2' 2.5(4) . . . . ? C10' N1' C12' N2' -178.5(4) . . . . ? C11' N2' C12' N1' -2.2(4) . . . . ? C13' N2' C12' N1' 175.5(3) . . . . ? C6 O1 C13 N2 -86.8(3) . . . . ? C12 N2 C13 O1 107.4(4) . . . . ? C11 N2 C13 O1 -67.0(4) . . . . ? C6' O1' C13' N2' -76.9(3) . . . . ? C12' N2' C13' O1' -70.3(4) . . . . ? C11' N2' C13' O1' 106.9(4) . . . . ? N2 C13 O1 C6 -86.8(3) . . . . ? N2' C13' O1' C6' -76.9(3) . . . . ? C12 N1 C10 C16 126.6(7) . . . . ? C12' N1' C10' C16' 32.3(7) . . . . ? C12 N2 C13 O1 107.4(4) . . . . ? C12' N2' C13' O1' -70.3(4) . . . . ? 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 C12 H12A O2 0.95 2.69 3.523(7) 146.2 . C13' H13D Cl2 0.99 2.92 3.821(4) 151.4 1_635 C16 H16B Cl2 0.98 2.90 3.819(8) 157.1 . C13' H13C Cl1 0.99 2.90 3.711(4) 140.0 1_545 C10' H10C O2 0.99 2.47 3.150(7) 125.4 1_545 C16' H16D Cl1 0.98 2.84 3.799(6) 164.8 . C9' H9'A Cl1 0.95 2.80 3.556(4) 137.5 2_544 C3' H3'A O1 1.00 2.57 3.361(4) 136.4 1_645 C12' H12B Cl1 0.95 2.77 3.352(4) 120.5 1_545 C12 H12A Cl1 0.95 2.75 3.565(5) 144.3 . C11' H11B Cl2 0.95 2.75 3.586(4) 146.8 1_635 C10' H10C O2 0.99 2.47 3.150(7) 125.4 1_545 C13 H13B Cl1 0.99 2.69 3.613(4) 154.9 . C9 H9A Cl2 0.95 2.61 3.516(5) 160.5 . C13 H13A Cl2 0.99 2.62 3.581(4) 162.5 1_545 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.468 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.047 data_1c _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-[(1R,2S,5R)--(--)--menthoxymethyl]-3-propylimidazolium chloride hemihydrate ; _chemical_name_common ? _chemical_melting_point 73 _chemical_formula_moiety 'C17H31N2O, 0.5 H2O, Cl' _chemical_formula_sum 'C17 H32 Cl N2 O1.50' _chemical_formula_weight 323.90 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 P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4408(10) _cell_length_b 34.119(4) _cell_length_c 12.1754(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.292(2) _cell_angle_gamma 90.00 _cell_volume 3921.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4932 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.56 _exptl_crystal_description Rectangular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7557 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details '(Sheldrick 2004, 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25347 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.1150 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.42 _reflns_number_total 17433 _reflns_number_gt 9974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 8051 Friedel pairs' _refine_ls_abs_structure_Flack -0.02(5) _chemical_absolute_configuration syn _refine_ls_number_reflns 17433 _refine_ls_number_parameters 846 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1471 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.001 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 1.24648(10) 0.22940(3) 0.23401(7) 0.0450(3) Uani 1 1 d . . . Cl2 Cl 0.87830(11) 0.31222(3) -0.18323(8) 0.0458(3) Uani 1 1 d . . . Cl3 Cl 1.37242(11) 0.15342(3) 0.90607(8) 0.0474(3) Uani 1 1 d . . . Cl4 Cl 0.73863(10) 0.23687(3) 0.48997(8) 0.0461(3) Uani 1 1 d . . . O1' O 0.9769(3) 0.32440(7) 0.1881(2) 0.0439(7) Uani 1 1 d . . . O1 O 1.4681(3) 0.14133(7) 0.5343(2) 0.0508(8) Uani 1 1 d . . . O2 O -0.0951(3) 0.36598(7) 0.4913(2) 0.0394(6) Uani 1 1 d . . . O2' O 0.4135(3) 0.09755(8) 0.2225(2) 0.0465(7) Uani 1 1 d . . . O10 O 0.5912(4) 0.28033(14) 0.6928(4) 0.0721(12) Uani 1 1 d . . . H1AW H 0.635(5) 0.2695(13) 0.636(4) 0.058(15) Uiso 1 1 d . . . H1BW H 1.138(5) 0.1988(14) 0.080(4) 0.061(16) Uiso 1 1 d . . . O11 O 1.0906(4) 0.18807(15) 0.0303(4) 0.0758(12) Uani 1 1 d . . . H2BW H 1.153(6) 0.1774(16) -0.008(5) 0.09(2) Uiso 1 1 d . . . H2AW H 0.649(5) 0.2864(15) 0.724(4) 0.053(18) Uiso 1 1 d . . . N1 N 1.3129(3) 0.19159(9) 0.5894(3) 0.0381(8) Uani 1 1 d . . . N1' N 0.8153(3) 0.27504(8) 0.1334(2) 0.0323(7) Uani 1 1 d . . . N2 N 1.1115(3) 0.20618(9) 0.6631(2) 0.0364(7) Uani 1 1 d . . . N2' N 0.6137(3) 0.26020(8) 0.0591(2) 0.0328(7) Uani 1 1 d . . . N3 N 0.0639(3) 0.31343(9) 0.5185(2) 0.0340(7) Uani 1 1 d . . . N3' N 0.5643(3) 0.15253(9) 0.2021(2) 0.0360(7) Uani 1 1 d . . . N4' N 0.7802(3) 0.16584(9) 0.2457(2) 0.0374(8) Uani 1 1 d . . . N4 N 0.2827(3) 0.30248(9) 0.4765(3) 0.0396(8) Uani 1 1 d . . . C1' C 0.9353(5) 0.42681(13) 0.0733(4) 0.0602(13) Uani 1 1 d . . . H1'A H 0.8673 0.4222 0.0125 0.072 Uiso 1 1 calc R . . H1'B H 0.9085 0.4517 0.1096 0.072 Uiso 1 1 calc R . . C1 C 1.4153(6) 0.04037(13) 0.6518(4) 0.0700(15) Uani 1 1 d . . . H1A H 1.3554 0.0470 0.7156 0.084 Uiso 1 1 calc R . . H1B H 1.3774 0.0160 0.6188 0.084 Uiso 1 1 calc R . . C2' C 1.1246(5) 0.36053(13) 0.0593(4) 0.0553(12) Uani 1 1 d . . . H2'A H 1.1915 0.3662 0.1202 0.066 Uiso 1 1 calc R . . H2'B H 1.1544 0.3356 0.0246 0.066 Uiso 1 1 calc R . . C2 C 1.6202(5) 0.10358(14) 0.6555(4) 0.0632(13) Uani 1 1 d . . . H2A H 1.6558 0.1278 0.6908 0.076 Uiso 1 1 calc R . . H2B H 1.6813 0.0979 0.5916 0.076 Uiso 1 1 calc R . . C3' C 1.1336(5) 0.39293(15) -0.0242(5) 0.0701(14) Uani 1 1 d . . . H3'A H 1.0682 0.3861 -0.0862 0.084 Uiso 1 1 calc R . . C3 C 1.6313(5) 0.06983(16) 0.7371(5) 0.0710(14) Uani 1 1 d . . . H3A H 1.5757 0.0776 0.8033 0.085 Uiso 1 1 calc R . . C4' C 1.0807(5) 0.43100(15) 0.0266(5) 0.0769(16) Uani 1 1 d . . . H4'A H 1.1469 0.4392 0.0856 0.092 Uiso 1 1 calc R . . H4'B H 1.0798 0.4518 -0.0301 0.092 Uiso 1 1 calc R . . C4 C 1.5623(7) 0.03310(16) 0.6907(5) 0.0853(18) Uani 1 1 d . . . H4A H 1.6197 0.0232 0.6288 0.102 Uiso 1 1 calc R . . H4B H 1.5610 0.0126 0.7482 0.102 Uiso 1 1 calc R . . C5' C 0.9228(5) 0.39278(12) 0.1577(3) 0.0471(10) Uani 1 1 d . . . H5'A H 0.9886 0.3992 0.2199 0.056 Uiso 1 1 calc R . . C5 C 1.4045(6) 0.07361(12) 0.5666(4) 0.0578(12) Uani 1 1 d . . . H5A H 1.4645 0.0659 0.5027 0.069 Uiso 1 1 calc R . . C6' C 0.9768(4) 0.35549(11) 0.1060(3) 0.0421(10) Uani 1 1 d . . . H6'A H 0.9111 0.3479 0.0450 0.051 Uiso 1 1 calc R . . C6 C 1.4705(5) 0.11030(11) 0.6160(3) 0.0465(11) Uani 1 1 d . . . H6A H 1.4119 0.1187 0.6799 0.056 Uiso 1 1 calc R . . C7' C 1.2818(6) 0.39715(17) -0.0714(6) 0.104(2) Uani 1 1 d . . . H7'A H 1.3102 0.3724 -0.1057 0.156 Uiso 1 1 calc R . . H7'B H 1.3485 0.4037 -0.0123 0.156 Uiso 1 1 calc R . . H7'C H 1.2820 0.4180 -0.1267 0.156 Uiso 1 1 calc R . . C7 C 1.7838(6) 0.0632(2) 0.7751(7) 0.130(3) Uani 1 1 d . . . H7A H 1.7883 0.0398 0.8215 0.195 Uiso 1 1 calc R . . H7B H 1.8161 0.0860 0.8174 0.195 Uiso 1 1 calc R . . H7C H 1.8448 0.0597 0.7110 0.195 Uiso 1 1 calc R . . C8' C 0.7744(5) 0.38884(14) 0.2069(3) 0.0553(12) Uani 1 1 d . . . H8'A H 0.7756 0.3655 0.2564 0.066 Uiso 1 1 calc R . . C8 C 1.2537(7) 0.07997(14) 0.5226(4) 0.0769(17) Uani 1 1 d . . . H8A H 1.2570 0.1035 0.4739 0.092 Uiso 1 1 calc R . . C9 C 1.2216(5) 0.20266(11) 0.5054(3) 0.0438(10) Uani 1 1 d . . . H9A H 1.2428 0.2037 0.4293 0.053 Uiso 1 1 calc R . . C9' C 0.7249(4) 0.26489(11) 0.2170(3) 0.0403(10) Uani 1 1 d . . . H9'A H 0.7470 0.2645 0.2932 0.048 Uiso 1 1 calc R . . C10 C 0.9994(4) 0.21258(12) 0.7448(3) 0.0486(11) Uani 1 1 d . . . H10A H 0.9480 0.2370 0.7264 0.058 Uiso 1 1 calc R . . H10B H 1.0436 0.2161 0.8181 0.058 Uiso 1 1 calc R . . C10' C 0.5027(4) 0.25331(12) -0.0230(3) 0.0456(10) Uani 1 1 d . . . H10C H 0.4521 0.2288 -0.0043 0.055 Uiso 1 1 calc R . . H10D H 0.5476 0.2495 -0.0956 0.055 Uiso 1 1 calc R . . C11' C 0.6004(4) 0.25578(11) 0.1713(3) 0.0392(9) Uani 1 1 d . . . H11A H 0.5176 0.2477 0.2091 0.047 Uiso 1 1 calc R . . C11 C 1.0972(5) 0.21160(12) 0.5526(3) 0.0449(10) Uani 1 1 d . . . H11B H 1.0140 0.2202 0.5155 0.054 Uiso 1 1 calc R . . C12 C 1.2432(4) 0.19384(10) 0.6838(3) 0.0324(8) Uani 1 1 d . . . H12A H 1.2808 0.1877 0.7542 0.039 Uiso 1 1 calc R . . C12' C 0.7458(4) 0.27184(10) 0.0383(3) 0.0318(8) Uani 1 1 d . . . H12B H 0.7838 0.2770 -0.0323 0.038 Uiso 1 1 calc R . . C13' C 0.9641(4) 0.28663(11) 0.1441(4) 0.0454(10) Uani 1 1 d . . . H13A H 1.0141 0.2678 0.1924 0.054 Uiso 1 1 calc R . . H13B H 1.0096 0.2858 0.0711 0.054 Uiso 1 1 calc R . . C13 C 1.4601(4) 0.17894(11) 0.5773(4) 0.0501(11) Uani 1 1 d . . . H13C H 1.5103 0.1974 0.5281 0.060 Uiso 1 1 calc R . . H13D H 1.5079 0.1796 0.6498 0.060 Uiso 1 1 calc R . . C14' C 0.6607(5) 0.38177(16) 0.1202(5) 0.0768(16) Uani 1 1 d . . . H14A H 0.6920 0.3611 0.0699 0.115 Uiso 1 1 calc R . . H14B H 0.6441 0.4060 0.0789 0.115 Uiso 1 1 calc R . . H14C H 0.5727 0.3736 0.1560 0.115 Uiso 1 1 calc R . . C14 C 1.1455(6) 0.08858(18) 0.6111(5) 0.0910(19) Uani 1 1 d . . . H14D H 1.0560 0.0966 0.5767 0.137 Uiso 1 1 calc R . . H14E H 1.1806 0.1097 0.6585 0.137 Uiso 1 1 calc R . . H14F H 1.1299 0.0650 0.6552 0.137 Uiso 1 1 calc R . . C15' C 0.7360(6) 0.42441(16) 0.2769(4) 0.0836(17) Uani 1 1 d . . . H15A H 0.6483 0.4191 0.3170 0.125 Uiso 1 1 calc R . . H15B H 0.7223 0.4473 0.2294 0.125 Uiso 1 1 calc R . . H15C H 0.8127 0.4297 0.3294 0.125 Uiso 1 1 calc R . . C15 C 1.206(2) 0.0454(3) 0.4505(9) 0.139(5) Uani 1 1 d . . . H15D H 1.284(13) 0.041(4) 0.395(11) 0.26(8) Uiso 1 1 d . . . H15E H 1.146(13) 0.055(4) 0.416(11) 0.24(7) Uiso 1 1 d . . . H15F H 1.189(7) 0.023(2) 0.499(6) 0.13(3) Uiso 1 1 d . . . C16' C 0.3989(5) 0.28554(13) -0.0313(4) 0.0571(12) Uani 1 1 d . . . H16A H 0.4475 0.3098 -0.0549 0.069 Uiso 1 1 calc R . . H16B H 0.3564 0.2904 0.0416 0.069 Uiso 1 1 calc R . . C16 C 0.8967(5) 0.17978(14) 0.7499(4) 0.0584(13) Uani 1 1 d . . . H16C H 0.9470 0.1554 0.7709 0.070 Uiso 1 1 calc R . . H16D H 0.8539 0.1757 0.6764 0.070 Uiso 1 1 calc R . . C17' C 0.2838(5) 0.27533(15) -0.1131(4) 0.0627(13) Uani 1 1 d . . . H17A H 0.2252 0.2985 -0.1272 0.094 Uiso 1 1 calc R . . H17B H 0.2246 0.2543 -0.0831 0.094 Uiso 1 1 calc R . . H17C H 0.3269 0.2665 -0.1818 0.094 Uiso 1 1 calc R . . C17 C 0.7815(5) 0.18805(15) 0.8319(4) 0.0687(14) Uani 1 1 d . . . H17D H 0.7186 0.1653 0.8371 0.103 Uiso 1 1 calc R . . H17E H 0.7268 0.2110 0.8080 0.103 Uiso 1 1 calc R . . H17F H 0.8241 0.1933 0.9040 0.103 Uiso 1 1 calc R . . C21 C -0.0477(5) 0.45395(13) 0.6724(4) 0.0631(13) Uani 1 1 d . . . H21A H 0.0200 0.4428 0.7265 0.076 Uiso 1 1 calc R . . H21B H -0.0173 0.4811 0.6561 0.076 Uiso 1 1 calc R . . C21' C 0.4849(6) 0.01459(14) 0.0287(4) 0.0749(16) Uani 1 1 d . . . H21C H 0.5254 -0.0118 0.0413 0.090 Uiso 1 1 calc R . . H21D H 0.5451 0.0282 -0.0256 0.090 Uiso 1 1 calc R . . C22 C -0.2439(4) 0.39006(13) 0.6393(3) 0.0493(11) Uani 1 1 d . . . H22A H -0.2764 0.3630 0.6543 0.059 Uiso 1 1 calc R . . H22B H -0.3092 0.4018 0.5846 0.059 Uiso 1 1 calc R . . C22' C 0.2666(5) 0.07203(14) 0.0764(4) 0.0559(12) Uani 1 1 d . . . H22C H 0.2242 0.0982 0.0643 0.067 Uiso 1 1 calc R . . H22D H 0.2086 0.0582 0.1317 0.067 Uiso 1 1 calc R . . C23' C 0.2643(6) 0.04898(15) -0.0316(4) 0.0731(16) Uani 1 1 d . . . H23A H 0.3193 0.0643 -0.0868 0.088 Uiso 1 1 calc R . . C23 C -0.2493(5) 0.41386(14) 0.7449(4) 0.0592(13) Uani 1 1 d . . . H23B H -0.1849 0.4010 0.7996 0.071 Uiso 1 1 calc R . . C24 C -0.1917(6) 0.45496(13) 0.7222(4) 0.0672(14) Uani 1 1 d . . . H24A H -0.2574 0.4688 0.6719 0.081 Uiso 1 1 calc R . . H24B H -0.1876 0.4699 0.7919 0.081 Uiso 1 1 calc R . . C24' C 0.3350(6) 0.01031(14) -0.0185(4) 0.0741(16) Uani 1 1 d . . . H24C H 0.3398 -0.0029 -0.0908 0.089 Uiso 1 1 calc R . . H24D H 0.2780 -0.0064 0.0310 0.089 Uiso 1 1 calc R . . C25 C -0.0419(4) 0.42973(12) 0.5669(3) 0.0482(10) Uani 1 1 d . . . H25A H -0.1107 0.4418 0.5141 0.058 Uiso 1 1 calc R . . C25' C 0.4876(5) 0.03737(13) 0.1361(4) 0.0598(13) Uani 1 1 d . . . H25B H 0.4297 0.0223 0.1903 0.072 Uiso 1 1 calc R . . C26 C -0.0953(4) 0.38875(11) 0.5922(3) 0.0392(9) Uani 1 1 d . . . H26A H -0.0302 0.3761 0.6467 0.047 Uiso 1 1 calc R . . C26' C 0.4162(4) 0.07668(12) 0.1195(3) 0.0441(10) Uani 1 1 d . . . H26B H 0.4722 0.0923 0.0654 0.053 Uiso 1 1 calc R . . C27' C 0.1123(7) 0.04476(18) -0.0754(5) 0.100(2) Uani 1 1 d . . . H27A H 0.1146 0.0345 -0.1506 0.149 Uiso 1 1 calc R . . H27B H 0.0658 0.0704 -0.0751 0.149 Uiso 1 1 calc R . . H27C H 0.0596 0.0266 -0.0285 0.149 Uiso 1 1 calc R . . C27 C -0.3969(6) 0.41428(18) 0.7927(5) 0.0931(19) Uani 1 1 d . . . H27D H -0.4340 0.3875 0.7951 0.140 Uiso 1 1 calc R . . H27E H -0.4587 0.4306 0.7467 0.140 Uiso 1 1 calc R . . H27F H -0.3934 0.4251 0.8672 0.140 Uiso 1 1 calc R . . C28 C 0.1031(5) 0.42939(14) 0.5103(5) 0.0755(16) Uani 1 1 d . . . H28A H 0.0987 0.4090 0.4513 0.091 Uiso 1 1 calc R . . C28' C 0.6374(7) 0.04174(19) 0.1851(6) 0.096(2) Uani 1 1 d . . . H28B H 0.6286 0.0654 0.2329 0.115 Uiso 1 1 calc R . . C29 C 0.1382(4) 0.30903(11) 0.6156(3) 0.0373(9) Uani 1 1 d . . . H29A H 0.1001 0.3106 0.6875 0.045 Uiso 1 1 calc R . . C29' C 0.6355(4) 0.15867(11) 0.1046(3) 0.0394(9) Uani 1 1 d . . . H29B H 0.5972 0.1574 0.0324 0.047 Uiso 1 1 calc R . . C30' C 0.9098(4) 0.17060(14) 0.3111(4) 0.0553(12) Uani 1 1 d . D . H30A H 0.8855 0.1818 0.3837 0.066 Uiso 1 1 calc R . . H30B H 0.9739 0.1892 0.2736 0.066 Uiso 1 1 calc R . . C30 C 0.4140(4) 0.29890(14) 0.4130(4) 0.0534(12) Uani 1 1 d . C . H30C H 0.3923 0.2880 0.3395 0.064 Uiso 1 1 calc R . . H30D H 0.4797 0.2807 0.4509 0.064 Uiso 1 1 calc R . . C31 C 0.2741(4) 0.30210(11) 0.5899(3) 0.0409(10) Uani 1 1 d . . . H31A H 0.3499 0.2978 0.6401 0.049 Uiso 1 1 calc R . . C31' C 0.7701(4) 0.16675(11) 0.1330(3) 0.0386(9) Uani 1 1 d . . . H31B H 0.8453 0.1722 0.0838 0.046 Uiso 1 1 calc R . . C32' C 0.6536(4) 0.15707(11) 0.2851(3) 0.0402(9) Uani 1 1 d . . . H32A H 0.6308 0.1545 0.3607 0.048 Uiso 1 1 calc R . . C32 C 0.1558(4) 0.30934(11) 0.4360(3) 0.0420(10) Uani 1 1 d . . . H32B H 0.1328 0.3111 0.3601 0.050 Uiso 1 1 calc R . . C33 C -0.0853(4) 0.32583(11) 0.5060(3) 0.0386(9) Uani 1 1 d . . . H33A H -0.1281 0.3123 0.4420 0.046 Uiso 1 1 calc R . . H33B H -0.1390 0.3182 0.5723 0.046 Uiso 1 1 calc R . . C33' C 0.4158(4) 0.13817(12) 0.2122(3) 0.0445(10) Uani 1 1 d . . . H33C H 0.3711 0.1502 0.2774 0.053 Uiso 1 1 calc R . . H33D H 0.3606 0.1461 0.1465 0.053 Uiso 1 1 calc R . . C34 C 0.2253(6) 0.41833(17) 0.5864(7) 0.113(3) Uani 1 1 d . . . H34A H 0.1986 0.3955 0.6304 0.170 Uiso 1 1 calc R . . H34B H 0.2468 0.4404 0.6352 0.170 Uiso 1 1 calc R . . H34C H 0.3090 0.4120 0.5426 0.170 Uiso 1 1 calc R . . C34' C 0.7463(8) 0.0526(3) 0.1100(10) 0.177(5) Uani 1 1 d . . . H34D H 0.7413 0.0809 0.0960 0.266 Uiso 1 1 calc R . . H34E H 0.7333 0.0384 0.0408 0.266 Uiso 1 1 calc R . . H34F H 0.8390 0.0461 0.1417 0.266 Uiso 1 1 calc R . . C35' C 0.6631(12) 0.0117(5) 0.2608(14) 0.330(12) Uani 1 1 d . . . H35A H 0.6847 0.0231 0.3328 0.495 Uiso 1 1 calc R . . H35B H 0.7437 -0.0041 0.2362 0.495 Uiso 1 1 calc R . . H35C H 0.5789 -0.0050 0.2663 0.495 Uiso 1 1 calc R . . C35 C 0.1318(7) 0.46877(17) 0.4539(6) 0.111(2) Uani 1 1 d . . . H35D H 0.2227 0.4676 0.4156 0.166 Uiso 1 1 calc R . . H35E H 0.1351 0.4896 0.5093 0.166 Uiso 1 1 calc R . . H35F H 0.0559 0.4743 0.4009 0.166 Uiso 1 1 calc R . . C36 C 0.4837(6) 0.33836(17) 0.4006(5) 0.0873(18) Uani 1 1 d . . . H36A H 0.5328 0.3432 0.4714 0.105 Uiso 0.50 1 calc PR A 1 H36B H 0.5593 0.3345 0.3456 0.105 Uiso 0.50 1 calc PR A 1 H36C H 0.5795 0.3358 0.3687 0.105 Uiso 0.50 1 d PR A 2 H36D H 0.4917 0.3516 0.4727 0.105 Uiso 0.50 1 d PR A 2 C36' C 0.9842(6) 0.1323(2) 0.3272(6) 0.096(2) Uani 1 1 d . . . H36E H 1.0621 0.1369 0.3805 0.115 Uiso 0.55 1 calc PR B 1 H36F H 1.0290 0.1255 0.2564 0.115 Uiso 0.55 1 calc PR B 1 H36G H 1.0625 0.1364 0.3804 0.115 Uiso 0.45 1 d PR B 2 H36H H 0.9170 0.1136 0.3605 0.115 Uiso 0.45 1 d PR B 2 C37A C 0.4224(17) 0.3721(5) 0.3742(17) 0.161(8) Uani 0.50 1 d P C 1 H37A H 0.4815 0.3939 0.4001 0.241 Uiso 0.50 1 calc PR C 1 H37B H 0.3290 0.3737 0.4087 0.241 Uiso 0.50 1 calc PR C 1 H37C H 0.4116 0.3738 0.2942 0.241 Uiso 0.50 1 calc PR C 1 C37C C 0.9028(14) 0.0960(4) 0.3662(15) 0.171(8) Uani 0.55 1 d P D 1 H37D H 0.9659 0.0732 0.3659 0.256 Uiso 0.55 1 calc PR D 1 H37E H 0.8224 0.0912 0.3168 0.256 Uiso 0.55 1 calc PR D 1 H37F H 0.8680 0.1005 0.4409 0.256 Uiso 0.55 1 calc PR D 1 C37B C 0.3795(11) 0.3642(4) 0.3240(10) 0.097(4) Uani 0.50 1 d P C 2 H37G H 0.4182 0.3907 0.3162 0.145 Uiso 0.50 1 calc PR C 2 H37H H 0.2857 0.3657 0.3579 0.145 Uiso 0.50 1 calc PR C 2 H37I H 0.3712 0.3520 0.2514 0.145 Uiso 0.50 1 calc PR C 2 C37D C 1.0360(16) 0.1171(4) 0.2407(13) 0.079(4) Uani 0.45 1 d P D 2 H37J H 1.078(11) 0.091(3) 0.258(8) 0.07(3) Uiso 0.45 1 d P E 2 H37K H 1.077(17) 0.134(5) 0.178(15) 0.16(7) Uiso 0.45 1 d P F 2 H37L H 0.943(10) 0.108(3) 0.181(8) 0.06(3) Uiso 0.45 1 d P G 2 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 0.0395(6) 0.0589(7) 0.0366(5) 0.0065(5) 0.0007(4) 0.0030(5) Cl2 0.0516(6) 0.0526(6) 0.0333(5) 0.0082(5) 0.0097(4) 0.0006(5) Cl3 0.0583(7) 0.0482(6) 0.0356(5) 0.0074(5) -0.0108(5) -0.0021(5) Cl4 0.0444(6) 0.0564(6) 0.0375(5) 0.0071(5) -0.0001(4) -0.0073(5) O1' 0.0518(18) 0.0380(16) 0.0417(15) 0.0025(12) -0.0101(13) -0.0034(13) O1 0.065(2) 0.0375(16) 0.0504(17) -0.0037(13) 0.0194(15) 0.0020(14) O2 0.0397(16) 0.0448(17) 0.0338(15) 0.0028(12) 0.0004(12) 0.0015(12) O2' 0.0488(18) 0.0519(18) 0.0387(16) 0.0017(13) 0.0022(13) -0.0099(14) O10 0.041(2) 0.116(3) 0.059(3) -0.009(2) 0.005(2) 0.002(2) O11 0.045(2) 0.124(4) 0.059(2) -0.010(2) -0.007(2) -0.007(2) N1 0.042(2) 0.0327(17) 0.039(2) -0.0016(14) 0.0030(16) -0.0048(14) N1' 0.0349(18) 0.0324(16) 0.0297(17) 0.0022(13) 0.0039(14) -0.0002(13) N2 0.038(2) 0.0362(17) 0.0348(18) 0.0013(14) -0.0052(15) 0.0000(15) N2' 0.0349(19) 0.0309(16) 0.0325(18) -0.0001(13) 0.0037(14) 0.0022(14) N3 0.0323(17) 0.0350(17) 0.0349(18) -0.0011(14) 0.0052(14) -0.0036(14) N3' 0.0344(18) 0.0375(17) 0.0362(18) -0.0003(15) 0.0021(14) 0.0036(15) N4' 0.0327(19) 0.0412(19) 0.0385(19) -0.0052(14) -0.0013(15) 0.0003(14) N4 0.0353(19) 0.049(2) 0.0348(19) -0.0024(14) 0.0048(15) 0.0009(15) C1' 0.065(3) 0.046(3) 0.070(3) 0.014(2) 0.013(3) 0.015(2) C1 0.107(5) 0.038(3) 0.064(3) 0.001(2) 0.001(3) 0.000(3) C2' 0.042(3) 0.047(3) 0.077(3) 0.011(2) 0.003(2) 0.004(2) C2 0.050(3) 0.062(3) 0.078(3) 0.005(3) 0.016(3) 0.006(2) C3' 0.060(3) 0.059(3) 0.092(4) 0.015(3) 0.023(3) 0.000(2) C3 0.053(3) 0.071(4) 0.089(4) 0.017(3) -0.005(3) 0.014(3) C4' 0.072(4) 0.052(3) 0.107(4) 0.026(3) 0.020(3) -0.003(3) C4 0.101(5) 0.069(4) 0.087(4) 0.022(3) 0.024(4) 0.032(4) C5' 0.051(3) 0.040(2) 0.050(3) 0.004(2) -0.001(2) 0.002(2) C5 0.090(4) 0.039(2) 0.045(3) -0.005(2) 0.002(2) 0.007(2) C6' 0.044(3) 0.036(2) 0.046(2) 0.0058(18) -0.005(2) 0.0016(18) C6 0.059(3) 0.040(2) 0.041(2) 0.0013(19) 0.014(2) 0.004(2) C7' 0.067(4) 0.079(4) 0.166(7) 0.038(4) 0.051(4) 0.004(3) C7 0.064(4) 0.142(7) 0.185(8) 0.068(6) -0.008(5) 0.023(4) C8' 0.069(3) 0.056(3) 0.041(3) 0.004(2) 0.013(2) 0.009(2) C8 0.118(5) 0.046(3) 0.066(3) 0.000(2) -0.025(4) -0.023(3) C9 0.066(3) 0.040(2) 0.025(2) 0.0028(17) -0.005(2) -0.008(2) C9' 0.055(3) 0.041(2) 0.025(2) 0.0026(17) 0.0078(19) 0.006(2) C10 0.046(3) 0.050(3) 0.051(3) -0.012(2) 0.005(2) 0.010(2) C10' 0.039(2) 0.048(3) 0.050(3) -0.0118(19) -0.002(2) -0.001(2) C11' 0.042(3) 0.041(2) 0.034(2) 0.0022(17) 0.0103(19) -0.0037(19) C11 0.050(3) 0.045(2) 0.039(2) 0.0037(19) -0.015(2) -0.001(2) C12 0.038(2) 0.028(2) 0.031(2) 0.0011(16) -0.0021(17) -0.0025(17) C12' 0.035(2) 0.033(2) 0.027(2) 0.0049(16) 0.0082(17) 0.0053(17) C13' 0.045(3) 0.032(2) 0.059(3) 0.0003(19) -0.004(2) -0.0006(18) C13 0.048(3) 0.039(2) 0.064(3) -0.001(2) 0.015(2) -0.005(2) C14' 0.052(3) 0.088(4) 0.091(4) -0.007(3) 0.020(3) 0.002(3) C14 0.085(4) 0.085(4) 0.102(5) 0.001(3) -0.027(4) -0.025(3) C15' 0.111(5) 0.082(4) 0.059(3) -0.004(3) 0.020(3) 0.027(3) C15 0.259(14) 0.057(4) 0.100(6) -0.007(4) -0.060(9) -0.048(6) C16' 0.071(3) 0.055(3) 0.045(3) -0.009(2) -0.016(2) 0.014(2) C16 0.075(4) 0.056(3) 0.045(3) -0.008(2) 0.021(2) -0.012(2) C17' 0.059(3) 0.079(3) 0.051(3) -0.003(2) -0.017(2) 0.015(3) C17 0.067(3) 0.091(4) 0.048(3) -0.005(3) 0.020(2) 0.002(3) C21 0.070(3) 0.046(3) 0.073(3) -0.009(2) -0.004(3) 0.004(2) C21' 0.103(5) 0.047(3) 0.074(4) -0.005(3) 0.004(3) -0.005(3) C22 0.043(3) 0.051(2) 0.055(3) 0.012(2) 0.011(2) 0.008(2) C22' 0.050(3) 0.066(3) 0.052(3) 0.014(2) -0.010(2) -0.014(2) C23' 0.100(4) 0.065(3) 0.054(3) 0.015(2) -0.024(3) -0.038(3) C23 0.061(3) 0.061(3) 0.056(3) 0.008(2) 0.017(2) 0.017(2) C24 0.090(4) 0.053(3) 0.059(3) -0.010(2) 0.006(3) 0.022(3) C24' 0.111(5) 0.053(3) 0.059(3) 0.001(2) -0.010(3) -0.030(3) C25 0.047(3) 0.042(2) 0.056(3) 0.002(2) 0.002(2) -0.005(2) C25' 0.069(3) 0.055(3) 0.055(3) 0.000(2) -0.002(2) -0.006(2) C26 0.041(2) 0.045(2) 0.032(2) -0.0014(18) -0.0017(18) 0.0048(19) C26' 0.048(3) 0.047(2) 0.038(2) 0.0074(19) 0.0001(19) -0.014(2) C27' 0.113(5) 0.098(4) 0.088(4) 0.014(3) -0.056(4) -0.042(4) C27 0.089(4) 0.102(5) 0.089(4) 0.005(3) 0.047(3) 0.021(4) C28 0.063(4) 0.053(3) 0.111(4) -0.011(3) 0.032(3) -0.022(3) C28' 0.083(5) 0.087(4) 0.117(5) -0.014(4) -0.035(4) 0.023(4) C29 0.041(2) 0.034(2) 0.037(2) 0.0053(17) 0.0037(18) -0.0013(18) C29' 0.045(2) 0.035(2) 0.038(2) 0.0029(17) -0.0033(18) 0.0029(18) C30' 0.038(3) 0.075(3) 0.053(3) -0.007(2) -0.012(2) -0.005(2) C30 0.040(3) 0.075(3) 0.046(3) -0.012(2) 0.010(2) 0.001(2) C31 0.042(3) 0.041(2) 0.040(2) 0.0048(17) -0.0024(18) -0.0007(19) C31' 0.042(2) 0.035(2) 0.039(2) 0.0000(17) 0.0015(18) -0.0003(18) C32' 0.043(2) 0.041(2) 0.037(2) -0.0011(18) -0.0014(19) 0.005(2) C32 0.047(3) 0.042(2) 0.037(2) -0.0060(18) 0.004(2) -0.007(2) C33 0.030(2) 0.039(2) 0.047(2) -0.0022(18) 0.0040(18) -0.0061(17) C33' 0.034(2) 0.054(3) 0.046(2) -0.002(2) -0.0011(18) 0.0015(19) C34 0.052(4) 0.062(4) 0.226(8) 0.004(4) 0.009(5) 0.000(3) C34' 0.065(5) 0.177(9) 0.290(13) -0.075(9) 0.026(7) -0.017(5) C35' 0.130(9) 0.42(2) 0.44(2) 0.294(19) -0.160(12) -0.053(11) C35 0.116(5) 0.075(4) 0.142(6) -0.005(4) 0.062(4) -0.048(4) C36 0.059(4) 0.096(4) 0.107(5) -0.001(4) 0.044(3) -0.007(3) C36' 0.066(4) 0.114(5) 0.108(5) 0.012(4) -0.044(4) 0.001(4) C37A 0.123(14) 0.122(14) 0.24(2) -0.020(14) 0.114(14) -0.032(12) C37C 0.124(11) 0.090(9) 0.30(2) 0.075(12) -0.144(13) -0.020(8) C37B 0.056(7) 0.125(10) 0.109(10) 0.078(8) 0.021(6) 0.011(7) C37D 0.087(10) 0.076(9) 0.074(9) -0.008(8) -0.018(8) 0.053(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1' C13' 1.400(4) . ? O1' C6' 1.458(4) . ? O1 C13 1.388(4) . ? O1 C6 1.453(4) . ? O2 C33 1.385(4) . ? O2 C26 1.453(4) . ? O2' C33' 1.392(5) . ? O2' C26' 1.442(5) . ? N1 C12 1.329(5) . ? N1 C9 1.386(5) . ? N1 C13 1.464(5) . ? N1' C12' 1.332(4) . ? N1' C9' 1.376(5) . ? N1' C13' 1.465(5) . ? N2 C12 1.335(4) . ? N2 C11 1.365(5) . ? N2 C10 1.472(5) . ? N2' C12' 1.334(4) . ? N2' C11' 1.380(5) . ? N2' C10' 1.464(5) . ? N3 C32 1.337(4) . ? N3 C29 1.379(5) . ? N3 C33 1.478(5) . ? N3' C32' 1.323(4) . ? N3' C29' 1.383(5) . ? N3' C33' 1.491(5) . ? N4' C32' 1.324(5) . ? N4' C31' 1.375(5) . ? N4' C30' 1.466(5) . ? N4 C32 1.315(5) . ? N4 C31 1.384(5) . ? N4 C30 1.469(5) . ? C1' C4' 1.496(6) . ? C1' C5' 1.556(6) . ? C1 C4 1.485(7) . ? C1 C5 1.540(6) . ? C2' C3' 1.505(6) . ? C2' C6' 1.519(6) . ? C2 C6 1.508(6) . ? C2 C3 1.523(7) . ? C3' C7' 1.522(7) . ? C3' C4' 1.524(7) . ? C3 C4 1.520(8) . ? C3 C7 1.527(7) . ? C5' C6' 1.510(6) . ? C5' C8' 1.532(6) . ? C5 C6 1.521(6) . ? C5 C8 1.534(7) . ? C8' C14' 1.521(7) . ? C8' C15' 1.528(6) . ? C8 C14 1.518(8) . ? C8 C15 1.538(8) . ? C9 C11 1.345(6) . ? C9' C11' 1.335(5) . ? C10 C16 1.482(6) . ? C10' C16' 1.476(5) . ? C16' C17' 1.510(6) . ? C16 C17 1.508(6) . ? C21 C24 1.492(6) . ? C21 C25 1.529(6) . ? C21' C25' 1.521(6) . ? C21' C24' 1.532(8) . ? C22 C26 1.519(5) . ? C22 C23 1.522(6) . ? C22' C26' 1.513(6) . ? C22' C23' 1.532(7) . ? C23' C24' 1.487(7) . ? C23' C27' 1.535(7) . ? C23 C27 1.512(6) . ? C23 C24 1.530(7) . ? C25 C26 1.518(5) . ? C25 C28 1.536(6) . ? C25' C26' 1.514(6) . ? C25' C28' 1.540(8) . ? C28 C34 1.523(8) . ? C28 C35 1.533(7) . ? C28' C35' 1.399(11) . ? C28' C34' 1.429(11) . ? C29 C31 1.343(5) . ? C29' C31' 1.344(5) . ? C30' C36' 1.495(7) . ? C30 C36 1.506(7) . ? C36 C37A 1.329(18) . ? C36 C37B 1.616(11) . ? C36' C37D 1.275(13) . ? C36' C37C 1.534(14) . ? 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 C13' O1' C6' 114.1(3) . . ? C13 O1 C6 114.6(3) . . ? C33 O2 C26 114.9(3) . . ? C33' O2' C26' 114.4(3) . . ? C12 N1 C9 108.3(3) . . ? C12 N1 C13 125.4(3) . . ? C9 N1 C13 126.3(3) . . ? C12' N1' C9' 108.5(3) . . ? C12' N1' C13' 124.6(3) . . ? C9' N1' C13' 126.8(3) . . ? C12 N2 C11 108.4(3) . . ? C12 N2 C10 126.3(3) . . ? C11 N2 C10 125.3(3) . . ? C12' N2' C11' 108.1(3) . . ? C12' N2' C10' 125.7(3) . . ? C11' N2' C10' 126.2(3) . . ? C32 N3 C29 107.7(3) . . ? C32 N3 C33 125.0(3) . . ? C29 N3 C33 126.8(3) . . ? C32' N3' C29' 109.1(3) . . ? C32' N3' C33' 124.8(3) . . ? C29' N3' C33' 125.6(3) . . ? C32' N4' C31' 108.0(3) . . ? C32' N4' C30' 125.5(3) . . ? C31' N4' C30' 126.4(3) . . ? C32 N4 C31 108.5(3) . . ? C32 N4 C30 126.0(3) . . ? C31 N4 C30 125.3(3) . . ? C4' C1' C5' 113.3(4) . . ? C4 C1 C5 113.3(5) . . ? C3' C2' C6' 113.0(4) . . ? C6 C2 C3 112.6(4) . . ? C2' C3' C7' 112.3(4) . . ? C2' C3' C4' 109.4(4) . . ? C7' C3' C4' 112.1(4) . . ? C4 C3 C2 110.7(4) . . ? C4 C3 C7 113.1(5) . . ? C2 C3 C7 111.7(5) . . ? C1' C4' C3' 112.1(4) . . ? C1 C4 C3 112.2(4) . . ? C6' C5' C8' 113.6(3) . . ? C6' C5' C1' 109.0(3) . . ? C8' C5' C1' 113.3(4) . . ? C6 C5 C8 113.5(4) . . ? C6 C5 C1 108.3(4) . . ? C8 C5 C1 113.4(4) . . ? O1' C6' C5' 109.0(3) . . ? O1' C6' C2' 110.0(3) . . ? C5' C6' C2' 111.9(3) . . ? O1 C6 C2 109.9(3) . . ? O1 C6 C5 108.9(3) . . ? C2 C6 C5 112.5(4) . . ? C14' C8' C15' 110.1(4) . . ? C14' C8' C5' 112.8(4) . . ? C15' C8' C5' 111.6(4) . . ? C14 C8 C5 114.0(4) . . ? C14 C8 C15 110.8(8) . . ? C5 C8 C15 111.2(8) . . ? C11 C9 N1 106.7(3) . . ? C11' C9' N1' 107.3(3) . . ? N2 C10 C16 112.9(3) . . ? N2' C10' C16' 113.5(3) . . ? C9' C11' N2' 107.6(3) . . ? C9 C11 N2 107.9(4) . . ? N1 C12 N2 108.7(3) . . ? N1' C12' N2' 108.4(3) . . ? O1' C13' N1' 111.3(3) . . ? O1 C13 N1 111.3(3) . . ? C10' C16' C17' 110.4(4) . . ? C10 C16 C17 111.2(4) . . ? C24 C21 C25 113.0(4) . . ? C25' C21' C24' 112.5(5) . . ? C26 C22 C23 111.7(4) . . ? C26' C22' C23' 111.1(4) . . ? C24' C23' C22' 111.1(4) . . ? C24' C23' C27' 111.9(4) . . ? C22' C23' C27' 110.8(5) . . ? C27 C23 C22 111.4(4) . . ? C27 C23 C24 112.9(4) . . ? C22 C23 C24 108.8(4) . . ? C21 C24 C23 112.2(4) . . ? C23' C24' C21' 111.7(4) . . ? C26 C25 C21 108.3(3) . . ? C26 C25 C28 112.4(3) . . ? C21 C25 C28 114.7(4) . . ? C26' C25' C21' 109.4(4) . . ? C26' C25' C28' 111.9(4) . . ? C21' C25' C28' 113.2(5) . . ? O2 C26 C25 108.6(3) . . ? O2 C26 C22 109.9(3) . . ? C25 C26 C22 111.0(3) . . ? O2' C26' C22' 109.5(3) . . ? O2' C26' C25' 109.4(3) . . ? C22' C26' C25' 111.6(4) . . ? C34 C28 C35 110.7(5) . . ? C34 C28 C25 113.7(5) . . ? C35 C28 C25 110.7(5) . . ? C35' C28' C34' 119.3(9) . . ? C35' C28' C25' 109.9(7) . . ? C34' C28' C25' 116.1(6) . . ? C31 C29 N3 107.6(3) . . ? C31' C29' N3' 105.9(3) . . ? N4' C30' C36' 111.4(4) . . ? N4 C30 C36 110.4(4) . . ? C29 C31 N4 106.9(3) . . ? C29' C31' N4' 108.2(3) . . ? N3' C32' N4' 108.8(3) . . ? N4 C32 N3 109.3(3) . . ? O2 C33 N3 111.0(3) . . ? O2' C33' N3' 110.5(3) . . ? C37A C36 C30 127.6(9) . . ? C37A C36 C37B 28.7(9) . . ? C30 C36 C37B 106.3(6) . . ? C37D C36' C30' 115.5(8) . . ? C37D C36' C37C 97.0(10) . . ? C30' C36' C37C 120.6(7) . . ? 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 N2 C10 C16 C17 -178.3(4) . . . . ? N2' C10' C16' C17' -176.9(4) . . . . ? N4 C30 C36 C37A -45.0(13) . . . . ? N4 C30 C36 C37B -66.9(6) . . . . ? N4' C30' C36' C37C -49.1(10) . . . . ? N4' C30' C36' C37D 67.0(11) . . . . ? 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 C32' H32A O1 0.95 2.66 3.551(5) 157.1 1_455 C32 H32B O1' 0.95 2.59 3.489(5) 157.2 1_455 C30 H30C Cl1 0.99 2.74 3.583(4) 143.1 1_455 C31' H31B O11 0.95 2.47 3.359(6) 156.1 . C31 H31A O10 0.95 2.44 3.323(6) 155.1 . C11 H11B Cl4 0.95 2.68 3.572(5) 156.9 . C30' H30A Cl4 0.99 2.67 3.535(5) 145.7 . C11' H11A Cl1 0.95 2.65 3.547(4) 157.0 1_455 C29 H29A Cl2 0.95 2.63 3.478(4) 149.4 1_456 C29' H29B Cl3 0.95 2.62 3.462(4) 148.2 1_454 C13' H13A Cl1 0.99 2.60 3.476(4) 147.3 . C13 H13C Cl4 0.99 2.59 3.461(4) 147.2 1_655 C9' H9'A Cl4 0.95 2.58 3.460(4) 155.0 . C9 H9A Cl1 0.95 2.53 3.438(4) 158.8 . C12' H12B Cl2 0.95 2.37 3.282(4) 160.0 . C12 H12A Cl3 0.95 2.35 3.268(4) 162.8 . O11 H1BW Cl1 0.83(5) 2.38(5) 3.205(5) 173(4) . O11 H2BW Cl3 0.83(6) 2.47(6) 3.287(5) 168(5) 1_554 O10 H1AW Cl4 0.89(5) 2.32(5) 3.204(5) 175(4) . O10 H2AW Cl2 0.70(5) 2.59(5) 3.281(5) 173(5) 1_556 _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.362 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.052