Electronic Supplementary Material for CrystEngComm this journal is (c) The royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm #============================================================================== # SUBMISSION DETAILS _journal_coden_Cambridge 1350 #============================================================================== _audit_creation_method 'manual editing of form.cif' _publ_contact_author_name 'Krzysztof Wozniak' _publ_contact_author_address ; Chemistry Department, Warsaw University, ul. Pasteura 1, 02-093 Warszawa, Poland ; _publ_contact_author_email kwozniak@chem.uw.edu.pl _publ_contact_author_fax 48(22)8222892 _publ_contact_author_phone '48(22)8220211 (ext. 216)' # TITLE AND AUTHOR LIST _publ_section_title ; Stacks of DMANH+ scaffolding for ribbon shaped Cl- bridged oxonium ions ; _publ_section_title_footnote ; Contribution No. ... ; loop_ _publ_author_name _publ_author_address 'Lukasz Dobrzycki' ; Chemistry Department, Warsaw University, ul. Pasteura 1, 02-093 Warszawa, Poland ; 'Maksymilian Chruszcz' ; Department of Molecular Physiology and Biological Physics, University of Virginia, Charlottesville, Virginia 22908, USA ; 'Wladek Minor' ; Department of Molecular Physiology and Biological Physics, University of Virginia, Charlottesville, Virginia 22908,USA ; K.Wozniak ; Chemistry Department, Warsaw University, ul. Pasteura 1, 02-093 Warszawa, Poland. ; _publ_section_abstract ; ? ; _publ_section_experimental ; ? ; _publ_section_comment ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; ############################################################# data_1 _database_code_depnum_ccdc_archive 'CCDC 622710' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Cl2 N2 O2' _chemical_formula_weight 323.25 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0850(10) _cell_length_b 9.8110(10) _cell_length_c 17.9150(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.6390(10) _cell_angle_gamma 90.00 _cell_volume 1736.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'RIGAKU R-AXIS RAPID' _diffrn_measurement_method 'omega scan with kappa offset' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10757 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 40.00 _reflns_number_total 10757 _reflns_number_gt 9211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL2000 (Otwinowski & Minor, 1997)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0539P)^2^+0.1626P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0114(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10757 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _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 0.012267(15) 0.900805(14) 0.667957(8) 0.02737(4) Uani 1 1 d . . . Cl2 Cl 0.476878(13) 0.908649(14) 0.845936(8) 0.02531(3) Uani 1 1 d . . . O1 O 0.13855(6) 0.64942(5) 0.74293(3) 0.02964(9) Uani 1 1 d . . . O2 O 0.38228(6) 0.65830(5) 0.75294(3) 0.03421(10) Uani 1 1 d . . . H1OA H 0.1030(14) 0.5836(14) 0.7179(8) 0.058(4) Uiso 1 1 d . . . H1OB H 0.1005(13) 0.7166(15) 0.7226(8) 0.056(4) Uiso 1 1 d . . . H2OA H 0.4127(15) 0.7209(17) 0.7787(8) 0.066(4) Uiso 1 1 d . . . H2OB H 0.4169(14) 0.5908(14) 0.7756(8) 0.058(4) Uiso 1 1 d . . . H3O H 0.2587(18) 0.650(2) 0.7461(9) 0.098(7) Uiso 1 1 d . . . N1 N 0.83470(4) 0.84192(4) 0.88232(2) 0.02007(7) Uani 1 1 d . . . N2 N 0.72557(4) 0.75195(4) 0.99264(2) 0.01831(6) Uani 1 1 d . . . C1 C 0.96605(5) 0.79633(5) 0.92471(3) 0.01899(7) Uani 1 1 d . . . C2 C 1.08152(5) 0.81874(6) 0.89676(3) 0.02378(9) Uani 1 1 d . . . C3 C 1.20919(5) 0.77519(6) 0.93742(3) 0.02604(9) Uani 1 1 d . . . C4 C 1.21936(5) 0.70864(6) 1.00547(3) 0.02360(9) Uani 1 1 d . . . C5 C 1.11363(6) 0.61167(6) 1.10605(3) 0.02404(9) Uani 1 1 d . . . C6 C 1.00137(6) 0.58433(7) 1.13573(3) 0.02701(10) Uani 1 1 d . . . C7 C 0.87266(6) 0.62931(6) 1.09747(3) 0.02396(9) Uani 1 1 d . . . C8 C 0.85915(5) 0.69955(5) 1.03009(3) 0.01850(7) Uani 1 1 d . . . C9 C 0.97229(5) 0.72676(5) 0.99559(3) 0.01767(7) Uani 1 1 d . . . C10 C 1.10211(5) 0.68169(5) 1.03578(3) 0.01979(7) Uani 1 1 d . . . C11 C 0.79205(6) 0.76543(8) 0.81018(3) 0.02979(11) Uani 1 1 d . . . C12 C 0.83103(7) 0.99054(7) 0.86906(5) 0.03504(14) Uani 1 1 d . . . C13 C 0.67617(6) 0.86034(6) 1.03850(3) 0.02711(10) Uani 1 1 d . . . C14 C 0.62301(6) 0.64201(6) 0.97236(3) 0.02548(9) Uani 1 1 d . . . H2N H 0.7479(13) 0.8027(13) 0.9407(8) 0.057(3) Uiso 1 1 d . . . H2 H 1.0732(12) 0.8668(12) 0.8460(7) 0.044(3) Uiso 1 1 d . . . H3 H 1.2906(11) 0.7901(11) 0.9164(6) 0.041(3) Uiso 1 1 d . . . H4 H 1.3049(10) 0.6762(10) 1.0336(6) 0.032(2) Uiso 1 1 d . . . H5 H 1.2017(11) 0.5829(10) 1.1306(6) 0.033(2) Uiso 1 1 d . . . H6 H 1.0103(10) 0.5369(11) 1.1830(6) 0.038(3) Uiso 1 1 d . . . H7 H 0.7912(11) 0.6135(10) 1.1185(6) 0.034(2) Uiso 1 1 d . . . H11A H 0.7932(11) 0.6657(11) 0.8218(6) 0.040(3) Uiso 1 1 d . . . H11B H 0.8540(12) 0.7827(12) 0.7758(7) 0.049(3) Uiso 1 1 d . . . H11C H 0.6990(11) 0.7934(11) 0.7877(6) 0.036(2) Uiso 1 1 d . . . H12A H 0.8647(12) 1.0421(13) 0.9184(7) 0.049(3) Uiso 1 1 d . . . H12B H 0.8890(12) 1.0163(12) 0.8339(7) 0.049(3) Uiso 1 1 d . . . H12C H 0.7378(10) 1.0139(11) 0.8472(6) 0.035(2) Uiso 1 1 d . . . H13A H 0.6563(11) 0.8207(12) 1.0849(7) 0.043(3) Uiso 1 1 d . . . H13B H 0.7453(11) 0.9268(10) 1.0520(6) 0.036(3) Uiso 1 1 d . . . H13C H 0.5949(11) 0.8991(11) 1.0078(7) 0.036(3) Uiso 1 1 d . . . H14A H 0.6062(12) 0.5973(11) 1.0180(7) 0.041(3) Uiso 1 1 d . . . H14B H 0.6576(11) 0.5771(11) 0.9395(6) 0.035(3) Uiso 1 1 d . . . H14C H 0.5449(10) 0.6818(10) 0.9420(6) 0.030(2) Uiso 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 0.02754(6) 0.02397(6) 0.02834(6) 0.00175(4) 0.00026(4) 0.00015(4) Cl2 0.02392(6) 0.02386(6) 0.02882(6) 0.00321(4) 0.00690(4) 0.00139(4) O1 0.0398(2) 0.02202(18) 0.02529(17) -0.00097(14) 0.00232(16) 0.00038(16) O2 0.0396(3) 0.0254(2) 0.0346(2) 0.00321(17) 0.00005(19) -0.00048(17) N1 0.02081(16) 0.01985(16) 0.02019(15) 0.00259(12) 0.00566(12) 0.00125(12) N2 0.01880(14) 0.01845(15) 0.01874(14) -0.00169(11) 0.00630(12) -0.00057(11) C1 0.01947(16) 0.01890(17) 0.01967(16) 0.00107(13) 0.00654(13) 0.00021(13) C2 0.02232(19) 0.0260(2) 0.0252(2) 0.00399(17) 0.01013(16) 0.00043(16) C3 0.02062(19) 0.0281(2) 0.0318(2) 0.00341(19) 0.01082(17) 0.00036(16) C4 0.01928(18) 0.0237(2) 0.0283(2) 0.00050(16) 0.00601(16) 0.00083(15) C5 0.0242(2) 0.0268(2) 0.02057(18) 0.00192(16) 0.00336(15) 0.00316(17) C6 0.0286(2) 0.0329(3) 0.02000(19) 0.00567(17) 0.00603(17) 0.00343(19) C7 0.0252(2) 0.0287(2) 0.01940(17) 0.00356(16) 0.00797(15) 0.00095(17) C8 0.01934(16) 0.01963(17) 0.01734(15) -0.00058(13) 0.00560(13) -0.00023(13) C9 0.01880(16) 0.01722(16) 0.01769(15) -0.00105(12) 0.00538(12) -0.00048(13) C10 0.01970(17) 0.01949(17) 0.02042(17) -0.00104(14) 0.00457(13) 0.00036(14) C11 0.0276(2) 0.0419(3) 0.01959(19) -0.00287(19) 0.00406(17) 0.0041(2) C12 0.0275(2) 0.0226(2) 0.0558(4) 0.0122(2) 0.0104(3) 0.00262(19) C13 0.0311(2) 0.0260(2) 0.0257(2) -0.00565(18) 0.00935(18) 0.00542(19) C14 0.0235(2) 0.0231(2) 0.0286(2) 0.00061(17) 0.00241(17) -0.00545(16) _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 H1OA 0.826(14) . ? O1 H1OB 0.811(15) . ? O1 H3O 1.202(18) . ? O2 H2OA 0.792(16) . ? O2 H2OB 0.818(14) . ? O2 H3O 1.230(18) . ? N1 C1 1.4579(7) . ? N1 C12 1.4766(8) . ? N1 C11 1.4813(7) . ? N2 C8 1.4713(6) . ? N2 C14 1.4878(7) . ? N2 C13 1.4897(7) . ? N2 H2N 1.117(13) . ? C1 C2 1.3749(7) . ? C1 C9 1.4318(6) . ? C2 C3 1.4116(8) . ? C2 H2 1.013(12) . ? C3 C4 1.3683(8) . ? C3 H3 0.981(11) . ? C4 C10 1.4220(7) . ? C4 H4 0.961(10) . ? C5 C6 1.3708(8) . ? C5 C10 1.4182(7) . ? C5 H5 0.951(11) . ? C6 C7 1.4109(8) . ? C6 H6 0.955(11) . ? C7 C8 1.3727(7) . ? C7 H7 0.984(11) . ? C8 C9 1.4281(6) . ? C9 C10 1.4310(7) . ? C11 H11A 1.000(11) . ? C11 H11B 0.977(12) . ? C11 H11C 0.983(11) . ? C12 H12A 1.015(13) . ? C12 H12B 0.976(12) . ? C12 H12C 0.970(10) . ? C13 H13A 0.974(12) . ? C13 H13B 0.949(11) . ? C13 H13C 0.968(11) . ? C14 H14A 0.971(12) . ? C14 H14B 0.979(11) . ? C14 H14C 0.947(10) . ? 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 H1OA O1 H1OB 106.2(13) . . ? H1OA O1 H3O 110.7(13) . . ? H1OB O1 H3O 113.4(13) . . ? H2OA O2 H2OB 105.2(14) . . ? H2OA O2 H3O 112.0(13) . . ? H2OB O2 H3O 108.7(14) . . ? C1 N1 C12 112.18(4) . . ? C1 N1 C11 111.86(4) . . ? C12 N1 C11 111.49(5) . . ? C8 N2 C14 112.67(4) . . ? C8 N2 C13 112.04(4) . . ? C14 N2 C13 111.03(4) . . ? C8 N2 H2N 102.5(7) . . ? C14 N2 H2N 111.5(7) . . ? C13 N2 H2N 106.7(7) . . ? C2 C1 C9 120.68(4) . . ? C2 C1 N1 120.57(4) . . ? C9 C1 N1 118.74(4) . . ? C1 C2 C3 121.00(5) . . ? C1 C2 H2 118.6(7) . . ? C3 C2 H2 120.4(7) . . ? C4 C3 C2 120.05(5) . . ? C4 C3 H3 119.7(7) . . ? C2 C3 H3 120.2(7) . . ? C3 C4 C10 120.69(5) . . ? C3 C4 H4 121.5(6) . . ? C10 C4 H4 117.8(6) . . ? C6 C5 C10 120.85(5) . . ? C6 C5 H5 122.0(6) . . ? C10 C5 H5 117.1(6) . . ? C5 C6 C7 120.09(5) . . ? C5 C6 H6 120.1(6) . . ? C7 C6 H6 119.8(6) . . ? C8 C7 C6 120.17(5) . . ? C8 C7 H7 118.3(6) . . ? C6 C7 H7 121.5(6) . . ? C7 C8 C9 121.89(4) . . ? C7 C8 N2 119.71(4) . . ? C9 C8 N2 118.38(4) . . ? C8 C9 C10 117.02(4) . . ? C8 C9 C1 125.23(4) . . ? C10 C9 C1 117.75(4) . . ? C5 C10 C4 120.24(5) . . ? C5 C10 C9 119.94(4) . . ? C4 C10 C9 119.82(4) . . ? N1 C11 H11A 108.9(6) . . ? N1 C11 H11B 110.6(7) . . ? H11A C11 H11B 108.6(9) . . ? N1 C11 H11C 107.6(6) . . ? H11A C11 H11C 109.2(9) . . ? H11B C11 H11C 111.9(10) . . ? N1 C12 H12A 111.1(7) . . ? N1 C12 H12B 111.2(7) . . ? H12A C12 H12B 107.1(10) . . ? N1 C12 H12C 106.8(6) . . ? H12A C12 H12C 111.1(9) . . ? H12B C12 H12C 109.7(9) . . ? N2 C13 H13A 109.5(7) . . ? N2 C13 H13B 108.7(6) . . ? H13A C13 H13B 108.8(10) . . ? N2 C13 H13C 107.8(7) . . ? H13A C13 H13C 110.2(9) . . ? H13B C13 H13C 111.7(9) . . ? N2 C14 H14A 110.6(7) . . ? N2 C14 H14B 107.7(6) . . ? H14A C14 H14B 110.8(9) . . ? N2 C14 H14C 107.4(6) . . ? H14A C14 H14C 113.8(9) . . ? H14B C14 H14C 106.2(9) . . ? 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 C12 N1 C1 C2 -58.82(7) . . . . ? C11 N1 C1 C2 67.33(6) . . . . ? C12 N1 C1 C9 121.75(5) . . . . ? C11 N1 C1 C9 -112.11(5) . . . . ? C9 C1 C2 C3 -0.67(8) . . . . ? N1 C1 C2 C3 179.90(5) . . . . ? C1 C2 C3 C4 0.50(9) . . . . ? C2 C3 C4 C10 0.45(9) . . . . ? C10 C5 C6 C7 -1.83(9) . . . . ? C5 C6 C7 C8 0.57(9) . . . . ? C6 C7 C8 C9 1.48(8) . . . . ? C6 C7 C8 N2 -176.94(5) . . . . ? C14 N2 C8 C7 -60.09(6) . . . . ? C13 N2 C8 C7 65.97(6) . . . . ? C14 N2 C8 C9 121.43(5) . . . . ? C13 N2 C8 C9 -112.50(5) . . . . ? C7 C8 C9 C10 -2.16(7) . . . . ? N2 C8 C9 C10 176.28(4) . . . . ? C7 C8 C9 C1 178.46(5) . . . . ? N2 C8 C9 C1 -3.10(7) . . . . ? C2 C1 C9 C8 179.28(5) . . . . ? N1 C1 C9 C8 -1.28(7) . . . . ? C2 C1 C9 C10 -0.09(7) . . . . ? N1 C1 C9 C10 179.35(4) . . . . ? C6 C5 C10 C4 -179.63(5) . . . . ? C6 C5 C10 C9 1.06(8) . . . . ? C3 C4 C10 C5 179.49(5) . . . . ? C3 C4 C10 C9 -1.20(8) . . . . ? C8 C9 C10 C5 0.89(7) . . . . ? C1 C9 C10 C5 -179.68(5) . . . . ? C8 C9 C10 C4 -178.42(5) . . . . ? C1 C9 C10 C4 1.01(7) . . . . ? 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 O1 H1OA Cl2 0.826(14) 2.129(14) 2.9533(5) 176.6(13) 2_546 O1 H1OB Cl1 0.811(15) 2.160(15) 2.9697(5) 176.2(13) . O2 H2OA Cl2 0.792(16) 2.224(16) 3.0129(6) 173.6(15) . O2 H2OB Cl1 0.818(14) 2.171(14) 2.9855(6) 173.8(14) 2_546 O1 H3O O2 1.202(18) 1.230(18) 2.4297(9) 175.5(18) . N2 H2N N1 1.117(13) 1.542(13) 2.6027(6) 155.9(11) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 40.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.572 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.049 data_2 _database_code_depnum_ccdc_archive 'CCDC 622711' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Cl2 N2 O2' _chemical_formula_weight 323.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6460(10) _cell_length_b 9.9010(10) _cell_length_c 10.1480(10) _cell_angle_alpha 70.5390(10) _cell_angle_beta 74.1320(10) _cell_angle_gamma 80.8870(10) _cell_volume 876.57(15) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'RIGAKU R-AXIS RAPID' _diffrn_measurement_method 'omega scan with kappa offset' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 10832 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0102 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 39.99 _reflns_number_total 10832 _reflns_number_gt 9861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL2000 (Otwinowski & Minor, 1997)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0542P)^2^+0.0644P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.040(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10832 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.165378(13) 0.133794(15) 0.195968(14) 0.02813(3) Uani 1 1 d . . . Cl2 Cl 0.675652(13) 0.173009(13) 0.168876(13) 0.02611(3) Uani 1 1 d . . . O1 O 0.46895(5) 0.11171(5) 0.02974(5) 0.02952(7) Uani 1 1 d . . . O2 O 0.97863(5) 0.11984(5) 0.01293(5) 0.03059(8) Uani 1 1 d . . . H1OA H 0.3883(15) 0.1183(14) 0.0739(14) 0.053(3) Uiso 1 1 d . . . H1OB H 0.5268(14) 0.1259(14) 0.0699(14) 0.052(3) Uiso 1 1 d . . . H2OA H 0.8959(14) 0.1322(13) 0.0562(13) 0.047(3) Uiso 1 1 d . . . H2OB H 1.0259(15) 0.1295(15) 0.0604(15) 0.061(4) Uiso 1 1 d . . . H3O1 H 0.5000 0.0000 0.0000 0.099(8) Uiso 1 2 d S . . H3O2 H 1.0000 0.0000 0.0000 0.103(8) Uiso 1 2 d S . . N1 N 0.23085(4) 0.45411(4) 0.26292(4) 0.01734(5) Uani 1 1 d . . . N2 N 0.22204(4) 0.23043(4) 0.48804(4) 0.01800(5) Uani 1 1 d . . . C1 C 0.26404(4) 0.53842(4) 0.34248(4) 0.01779(6) Uani 1 1 d . . . C2 C 0.28830(6) 0.68139(5) 0.27745(5) 0.02620(8) Uani 1 1 d . . . C3 C 0.31765(7) 0.76404(5) 0.35486(7) 0.03162(10) Uani 1 1 d . . . C4 C 0.32032(6) 0.70294(5) 0.49670(6) 0.02763(9) Uani 1 1 d . . . C5 C 0.30109(6) 0.49271(6) 0.71389(6) 0.02811(9) Uani 1 1 d . . . C6 C 0.28026(8) 0.35017(6) 0.78218(6) 0.03224(11) Uani 1 1 d . . . C7 C 0.25568(7) 0.26317(5) 0.70664(5) 0.02667(8) Uani 1 1 d . . . C8 C 0.24958(4) 0.32131(4) 0.56499(4) 0.01804(6) Uani 1 1 d . . . C9 C 0.26988(4) 0.46956(4) 0.48922(4) 0.01676(6) Uani 1 1 d . . . C10 C 0.29774(5) 0.55526(5) 0.56692(5) 0.02125(7) Uani 1 1 d . . . C11 C 0.34682(6) 0.45220(5) 0.13322(5) 0.02564(8) Uani 1 1 d . . . C12 C 0.08892(6) 0.50202(6) 0.22605(6) 0.02761(9) Uani 1 1 d . . . C13 C 0.07996(7) 0.16731(8) 0.55383(6) 0.03402(12) Uani 1 1 d . . . C14 C 0.34168(7) 0.11791(5) 0.47140(6) 0.02837(9) Uani 1 1 d . . . H2N H 0.2238(13) 0.3133(13) 0.3752(13) 0.056(3) Uiso 1 1 d . . . H2 H 0.2865(11) 0.7233(12) 0.1782(12) 0.041(3) Uiso 1 1 d . . . H3 H 0.3291(13) 0.8682(14) 0.3042(13) 0.054(3) Uiso 1 1 d . . . H4 H 0.3389(12) 0.7574(12) 0.5509(12) 0.043(3) Uiso 1 1 d . . . H5 H 0.3206(12) 0.5530(12) 0.7616(12) 0.044(3) Uiso 1 1 d . . . H6 H 0.2810(13) 0.3066(13) 0.8812(13) 0.053(3) Uiso 1 1 d . . . H7 H 0.2415(12) 0.1618(12) 0.7559(12) 0.041(3) Uiso 1 1 d . . . H11A H 0.4363(11) 0.4145(11) 0.1620(11) 0.034(2) Uiso 1 1 d . . . H11B H 0.3578(11) 0.5496(11) 0.0647(11) 0.039(2) Uiso 1 1 d . . . H11C H 0.3240(11) 0.3897(10) 0.0907(10) 0.033(2) Uiso 1 1 d . . . H12A H 0.0133(11) 0.5020(11) 0.3114(11) 0.037(2) Uiso 1 1 d . . . H12B H 0.0898(12) 0.5993(12) 0.1596(12) 0.040(3) Uiso 1 1 d . . . H12C H 0.0692(11) 0.4345(11) 0.1859(10) 0.033(2) Uiso 1 1 d . . . H13A H 0.0818(13) 0.0990(13) 0.6442(13) 0.049(3) Uiso 1 1 d . . . H13B H 0.0076(13) 0.2426(13) 0.5662(13) 0.047(3) Uiso 1 1 d . . . H13C H 0.0660(12) 0.1226(12) 0.4859(12) 0.041(3) Uiso 1 1 d . . . H14A H 0.3510(11) 0.0551(12) 0.5625(12) 0.042(3) Uiso 1 1 d . . . H14B H 0.4308(11) 0.1631(11) 0.4226(11) 0.039(2) Uiso 1 1 d . . . H14C H 0.3148(12) 0.0682(12) 0.4181(12) 0.043(3) Uiso 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 0.02475(5) 0.03323(6) 0.03116(6) -0.01498(5) -0.00763(4) -0.00254(4) Cl2 0.02379(5) 0.02845(5) 0.02830(5) -0.01184(4) -0.00691(4) 0.00003(4) O1 0.02515(16) 0.03568(19) 0.03033(17) -0.01284(15) -0.00767(13) -0.00165(14) O2 0.02386(16) 0.0408(2) 0.02971(17) -0.01400(15) -0.00638(13) -0.00263(14) N1 0.01773(12) 0.01768(12) 0.01553(11) -0.00520(9) -0.00292(9) 0.00023(9) N2 0.02008(13) 0.01581(11) 0.01713(12) -0.00486(9) -0.00204(10) -0.00311(10) C1 0.01865(14) 0.01587(12) 0.01738(13) -0.00454(10) -0.00206(10) -0.00218(10) C2 0.0347(2) 0.01702(15) 0.02330(17) -0.00315(13) -0.00277(15) -0.00574(14) C3 0.0414(3) 0.01888(17) 0.0336(2) -0.00731(16) -0.0037(2) -0.01019(17) C4 0.0300(2) 0.02254(17) 0.0344(2) -0.01282(16) -0.00624(17) -0.00691(15) C5 0.0335(2) 0.0306(2) 0.0278(2) -0.01380(17) -0.01452(17) -0.00036(17) C6 0.0474(3) 0.0310(2) 0.02322(18) -0.00890(16) -0.0179(2) 0.0013(2) C7 0.0389(2) 0.02209(17) 0.01922(16) -0.00375(13) -0.01143(16) -0.00044(16) C8 0.02069(15) 0.01677(13) 0.01671(13) -0.00490(10) -0.00493(11) -0.00110(11) C9 0.01602(13) 0.01650(13) 0.01794(13) -0.00580(10) -0.00347(10) -0.00151(10) C10 0.02073(16) 0.02178(15) 0.02486(16) -0.01059(13) -0.00654(13) -0.00223(12) C11 0.0289(2) 0.02492(17) 0.01839(15) -0.00737(13) 0.00277(14) -0.00178(15) C12 0.02425(19) 0.02803(19) 0.0339(2) -0.01188(17) -0.01349(17) 0.00547(15) C13 0.0325(2) 0.0429(3) 0.0279(2) -0.0142(2) 0.00572(18) -0.0216(2) C14 0.0374(2) 0.02138(17) 0.02668(19) -0.00979(15) -0.01110(17) 0.00849(16) _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 H1OA 0.790(14) . ? O1 H1OB 0.827(13) . ? O1 H3O1 1.2133(5) . ? O2 H2OA 0.811(13) . ? O2 H2OB 0.783(15) . ? O2 H3O2 1.2162(5) . ? N1 C1 1.4581(5) . ? N1 C11 1.4795(6) . ? N1 C12 1.4817(6) . ? N1 H2N 1.475(12) . ? N2 C8 1.4654(5) . ? N2 C13 1.4857(6) . ? N2 C14 1.4877(6) . ? N2 H2N 1.163(12) . ? C1 C2 1.3755(6) . ? C1 C9 1.4293(6) . ? C2 C3 1.4108(8) . ? C2 H2 0.957(11) . ? C3 C4 1.3688(9) . ? C3 H3 0.996(13) . ? C4 C10 1.4195(7) . ? C4 H4 0.953(11) . ? C5 C6 1.3691(8) . ? C5 C10 1.4191(7) . ? C5 H5 0.951(11) . ? C6 C7 1.4107(7) . ? C6 H6 0.954(12) . ? C7 C8 1.3730(6) . ? C7 H7 0.973(11) . ? C8 C9 1.4286(6) . ? C9 C10 1.4310(6) . ? C11 H11A 0.965(10) . ? C11 H11B 0.985(11) . ? C11 H11C 0.944(10) . ? C12 H12A 0.968(10) . ? C12 H12B 0.975(11) . ? C12 H12C 0.956(10) . ? C13 H13A 0.943(12) . ? C13 H13B 0.953(12) . ? C13 H13C 0.981(11) . ? C14 H14A 0.945(11) . ? C14 H14B 0.962(11) . ? C14 H14C 0.947(11) . ? 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 H1OA O1 H1OB 111.8(12) . . ? H1OA O1 H3O1 112.9(9) . . ? H1OB O1 H3O1 112.2(9) . . ? H2OA O2 H2OB 104.7(13) . . ? H2OA O2 H3O2 110.1(9) . . ? H2OB O2 H3O2 111.5(11) . . ? C1 N1 C11 112.14(4) . . ? C1 N1 C12 112.10(3) . . ? C11 N1 C12 111.04(4) . . ? C1 N1 H2N 98.5(5) . . ? C11 N1 H2N 112.1(5) . . ? C12 N1 H2N 110.4(5) . . ? C8 N2 C13 112.50(4) . . ? C8 N2 C14 112.00(4) . . ? C13 N2 C14 111.47(4) . . ? C8 N2 H2N 100.9(6) . . ? C13 N2 H2N 111.3(6) . . ? C14 N2 H2N 108.1(6) . . ? C2 C1 C9 120.91(4) . . ? C2 C1 N1 120.49(4) . . ? C9 C1 N1 118.60(3) . . ? C1 C2 C3 120.67(5) . . ? C1 C2 H2 118.7(7) . . ? C3 C2 H2 120.6(7) . . ? C4 C3 C2 120.16(4) . . ? C4 C3 H3 122.4(7) . . ? C2 C3 H3 117.3(7) . . ? C3 C4 C10 120.77(4) . . ? C3 C4 H4 121.3(7) . . ? C10 C4 H4 117.9(7) . . ? C6 C5 C10 120.76(4) . . ? C6 C5 H5 121.8(7) . . ? C10 C5 H5 117.4(7) . . ? C5 C6 C7 120.19(5) . . ? C5 C6 H6 121.9(7) . . ? C7 C6 H6 117.9(7) . . ? C8 C7 C6 120.31(5) . . ? C8 C7 H7 120.0(6) . . ? C6 C7 H7 119.7(6) . . ? C7 C8 C9 121.60(4) . . ? C7 C8 N2 119.88(4) . . ? C9 C8 N2 118.51(3) . . ? C8 C9 C1 125.03(3) . . ? C8 C9 C10 117.21(4) . . ? C1 C9 C10 117.76(4) . . ? C5 C10 C4 120.39(4) . . ? C5 C10 C9 119.91(4) . . ? C4 C10 C9 119.69(4) . . ? N1 C11 H11A 108.8(6) . . ? N1 C11 H11B 110.8(6) . . ? H11A C11 H11B 109.8(8) . . ? N1 C11 H11C 108.6(6) . . ? H11A C11 H11C 108.1(8) . . ? H11B C11 H11C 110.8(8) . . ? N1 C12 H12A 110.7(6) . . ? N1 C12 H12B 110.9(6) . . ? H12A C12 H12B 107.7(9) . . ? N1 C12 H12C 107.1(6) . . ? H12A C12 H12C 108.5(8) . . ? H12B C12 H12C 111.9(8) . . ? N2 C13 H13A 109.8(7) . . ? N2 C13 H13B 108.4(7) . . ? H13A C13 H13B 109.4(10) . . ? N2 C13 H13C 105.5(7) . . ? H13A C13 H13C 111.5(9) . . ? H13B C13 H13C 112.2(9) . . ? N2 C14 H14A 110.4(7) . . ? N2 C14 H14B 109.2(6) . . ? H14A C14 H14B 108.7(9) . . ? N2 C14 H14C 105.1(7) . . ? H14A C14 H14C 110.8(9) . . ? H14B C14 H14C 112.7(9) . . ? 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 C11 N1 C1 C2 58.86(5) . . . . ? C12 N1 C1 C2 -66.84(5) . . . . ? C11 N1 C1 C9 -121.52(4) . . . . ? C12 N1 C1 C9 112.79(4) . . . . ? C9 C1 C2 C3 -0.86(8) . . . . ? N1 C1 C2 C3 178.75(5) . . . . ? C1 C2 C3 C4 -0.91(9) . . . . ? C2 C3 C4 C10 1.76(9) . . . . ? C10 C5 C6 C7 0.26(10) . . . . ? C5 C6 C7 C8 -1.30(10) . . . . ? C6 C7 C8 C9 0.99(8) . . . . ? C6 C7 C8 N2 -179.17(5) . . . . ? C13 N2 C8 C7 61.02(6) . . . . ? C14 N2 C8 C7 -65.47(6) . . . . ? C13 N2 C8 C9 -119.13(5) . . . . ? C14 N2 C8 C9 114.38(4) . . . . ? C7 C8 C9 C1 -179.47(4) . . . . ? N2 C8 C9 C1 0.69(6) . . . . ? C7 C8 C9 C10 0.34(6) . . . . ? N2 C8 C9 C10 -179.51(4) . . . . ? C2 C1 C9 C8 -178.49(4) . . . . ? N1 C1 C9 C8 1.89(6) . . . . ? C2 C1 C9 C10 1.71(6) . . . . ? N1 C1 C9 C10 -177.92(3) . . . . ? C6 C5 C10 C4 -179.61(6) . . . . ? C6 C5 C10 C9 1.08(8) . . . . ? C3 C4 C10 C5 179.82(5) . . . . ? C3 C4 C10 C9 -0.87(8) . . . . ? C8 C9 C10 C5 -1.36(6) . . . . ? C1 C9 C10 C5 178.46(4) . . . . ? C8 C9 C10 C4 179.33(4) . . . . ? C1 C9 C10 C4 -0.85(6) . . . . ? 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 O1 H1OA Cl1 0.790(14) 2.179(14) 2.9682(5) 179.3(13) . O1 H1OB Cl2 0.827(13) 2.145(13) 2.9717(5) 177.4(13) . O2 H2OA Cl2 0.811(13) 2.166(13) 2.9768(5) 178.0(12) . O2 H2OB Cl1 0.783(15) 2.185(15) 2.9654(5) 174.2(14) 1_655 O1 H3O1 O1 1.21 1.21 2.4267(9) 180.00(4) 2_655 O2 H3O2 O2 1.22 1.22 2.4324(10) 180.00(4) 2_755 N2 H2N N1 1.163(12) 1.475(12) 2.5910(5) 158.2(11) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 39.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.517 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.051 data_3 _database_code_depnum_ccdc_archive 'CCDC 622712' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H51 Cl3 N4 O6' _chemical_formula_weight 646.08 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)/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 23.2912(9) _cell_length_b 11.9028(4) _cell_length_c 13.1852(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.417(3) _cell_angle_gamma 90.00 _cell_volume 3523.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 KM4CCD _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 153798 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.1283 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 39.50 _reflns_number_total 20845 _reflns_number_gt 9309 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.0444P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 20845 _refine_ls_number_parameters 589 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 0.806 _refine_ls_restrained_S_all 0.806 _refine_ls_shift/su_max 0.003 _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 0.981844(11) 0.21477(2) 0.651818(18) 0.02274(5) Uani 1 1 d . . . Cl2 Cl 0.749611(12) 0.15323(2) 0.64465(2) 0.03030(6) Uani 1 1 d . . . Cl3 Cl 0.518188(11) 0.27072(2) 0.64505(2) 0.02560(6) Uani 1 1 d . . . O1 O 0.88240(4) 0.27556(9) 0.27331(7) 0.0410(2) Uani 1 1 d . . . O2 O 0.88906(3) 0.33171(7) 0.47455(7) 0.02870(17) Uani 1 1 d . . . O3 O 0.78353(4) 0.32798(8) 0.49855(7) 0.0376(2) Uani 1 1 d . . . O4A O 0.70699(6) 0.34898(12) 0.33957(10) 0.0314(3) Uani 0.60 1 d P . . O4B O 0.72104(9) 0.22907(19) 0.32589(16) 0.0347(5) Uani 0.40 1 d P . . O5A O 0.62473(11) 0.20979(19) 0.3375(2) 0.0359(5) Uani 0.60 1 d P . . O5B O 0.61775(16) 0.2607(3) 0.3413(3) 0.0382(8) Uani 0.40 1 d P . . O6 O 0.61019(4) 0.17307(7) 0.52884(7) 0.03431(19) Uani 1 1 d . . . H1OA H 0.9072(7) 0.2785(12) 0.2375(12) 0.049(4) Uiso 1 1 d . . . H1OB H 0.8485(8) 0.2933(13) 0.2363(13) 0.058(5) Uiso 1 1 d . . . H2OA H 0.8907(6) 0.3095(10) 0.4142(11) 0.029(3) Uiso 1 1 d . . . H2OB H 0.9165(7) 0.3034(13) 0.5222(12) 0.054(5) Uiso 1 1 d . . . H3OA H 0.8239(9) 0.3224(14) 0.4961(13) 0.076(6) Uiso 1 1 d . . . H3OB H 0.7790(8) 0.2748(14) 0.5473(14) 0.069(5) Uiso 1 1 d . . . H4O H 0.7224(9) 0.3197(17) 0.2729(16) 0.103 Uiso 1 1 d . . . H5OA H 0.6169(7) 0.2117(15) 0.3963(14) 0.062(5) Uiso 1 1 d . . . H5OB H 0.5924(12) 0.241(2) 0.288(2) 0.127(10) Uiso 1 1 d . . . H6OA H 0.6470(7) 0.1744(12) 0.5717(12) 0.052(4) Uiso 1 1 d . . . H6OB H 0.5878(8) 0.1973(15) 0.5657(14) 0.078 Uiso 1 1 d . . . H7O H 0.7483(9) 0.3102(16) 0.4082(16) 0.088(6) Uiso 1 1 d . . . H8O H 0.6711(13) 0.275(2) 0.3320(19) 0.131 Uiso 1 1 d . . . N1A N 0.91379(3) 0.66038(6) 0.58166(6) 0.01458(14) Uani 1 1 d . . . N2A N 0.93379(3) 0.87276(6) 0.61523(6) 0.01482(14) Uani 1 1 d . . . C1A C 0.87021(4) 0.68747(7) 0.48297(7) 0.01404(16) Uani 1 1 d . . . C2A C 0.83996(4) 0.60366(8) 0.41901(7) 0.01720(17) Uani 1 1 d . . . C3A C 0.79665(4) 0.62963(8) 0.32509(7) 0.01895(18) Uani 1 1 d . . . C4A C 0.78429(4) 0.73930(8) 0.29678(7) 0.01853(18) Uani 1 1 d . . . C5A C 0.80250(4) 0.94186(8) 0.32949(7) 0.02070(19) Uani 1 1 d . . . C6A C 0.83300(5) 1.02777(9) 0.38888(8) 0.0239(2) Uani 1 1 d . . . C7A C 0.87671(4) 1.00452(8) 0.48327(8) 0.02049(19) Uani 1 1 d . . . C8A C 0.88900(4) 0.89589(7) 0.51524(7) 0.01532(16) Uani 1 1 d . . . C9A C 0.85944(4) 0.80301(7) 0.45514(7) 0.01389(16) Uani 1 1 d . . . C10A C 0.81507(4) 0.82834(8) 0.36009(7) 0.01590(17) Uani 1 1 d . . . C11A C 0.88647(5) 0.60057(9) 0.65516(8) 0.0230(2) Uani 1 1 d . . . C12A C 0.96545(4) 0.59832(9) 0.56485(8) 0.0225(2) Uani 1 1 d . . . C13A C 0.99527(4) 0.90633(9) 0.61327(8) 0.02045(18) Uani 1 1 d . . . C14A C 0.91687(5) 0.92248(9) 0.70692(8) 0.0226(2) Uani 1 1 d . . . H2NA H 0.9318(7) 0.7794(12) 0.6187(11) 0.055(4) Uiso 1 1 d . . . H2A H 0.8487(5) 0.5289(9) 0.4383(8) 0.017(3) Uiso 1 1 d . . . H3A H 0.7773(5) 0.5727(9) 0.2840(9) 0.021(3) Uiso 1 1 d . . . H4A H 0.7552(5) 0.7591(9) 0.2347(8) 0.018(3) Uiso 1 1 d . . . H5A H 0.7740(5) 0.9596(10) 0.2664(9) 0.025(3) Uiso 1 1 d . . . H6A H 0.8258(5) 1.1028(10) 0.3666(9) 0.027(3) Uiso 1 1 d . . . H7A H 0.8985(5) 1.0628(10) 0.5260(9) 0.028(3) Uiso 1 1 d . . . H11A H 0.8517(5) 0.6411(10) 0.6633(9) 0.023(3) Uiso 1 1 d . . . H11B H 0.8713(5) 0.5321(11) 0.6274(10) 0.032(3) Uiso 1 1 d . . . H11C H 0.9134(5) 0.6025(9) 0.7248(9) 0.022(3) Uiso 1 1 d . . . H12A H 0.9796(5) 0.6366(10) 0.5104(9) 0.025(3) Uiso 1 1 d . . . H12B H 0.9541(5) 0.5282(11) 0.5371(9) 0.031(3) Uiso 1 1 d . . . H12C H 0.9950(5) 0.5950(9) 0.6308(9) 0.024(3) Uiso 1 1 d . . . H13A H 0.9969(5) 0.9910(9) 0.6111(8) 0.021(3) Uiso 1 1 d . . . H13B H 1.0039(5) 0.8713(10) 0.5528(9) 0.028(3) Uiso 1 1 d . . . H13C H 1.0230(5) 0.8759(10) 0.6785(9) 0.024(3) Uiso 1 1 d . . . H14A H 0.9193(5) 1.0059(10) 0.7055(9) 0.025(3) Uiso 1 1 d . . . H14B H 0.8766(5) 0.9012(10) 0.7026(9) 0.025(3) Uiso 1 1 d . . . H14C H 0.9424(5) 0.8946(9) 0.7702(9) 0.024(3) Uiso 1 1 d . . . N1B N 0.58696(3) 0.83659(6) 0.67418(6) 0.01638(15) Uani 1 1 d . . . N2B N 0.56598(3) 0.62416(7) 0.68773(6) 0.01650(15) Uani 1 1 d . . . C1B C 0.63143(4) 0.80883(7) 0.61825(7) 0.01499(16) Uani 1 1 d . . . C2B C 0.66380(4) 0.89133(8) 0.58699(7) 0.01891(18) Uani 1 1 d . . . C3B C 0.70786(4) 0.86437(8) 0.53527(7) 0.02029(18) Uani 1 1 d . . . C4B C 0.71797(4) 0.75523(8) 0.51518(7) 0.01834(18) Uani 1 1 d . . . C5B C 0.69707(4) 0.55341(8) 0.52607(7) 0.02006(18) Uani 1 1 d . . . C6B C 0.66599(5) 0.46787(8) 0.55561(8) 0.0235(2) Uani 1 1 d . . . C7B C 0.62189(4) 0.49196(8) 0.60764(8) 0.02091(19) Uani 1 1 d . . . C8B C 0.61033(4) 0.60040(8) 0.62908(7) 0.01593(16) Uani 1 1 d . . . C9B C 0.64073(4) 0.69306(7) 0.59868(6) 0.01424(16) Uani 1 1 d . . . C10B C 0.68546(4) 0.66670(8) 0.54592(7) 0.01574(16) Uani 1 1 d . . . C11B C 0.50486(4) 0.58722(9) 0.63073(9) 0.0228(2) Uani 1 1 d . . . C12B C 0.58500(5) 0.57743(10) 0.79649(8) 0.0255(2) Uani 1 1 d . . . C13B C 0.61388(5) 0.89157(10) 0.77588(8) 0.0255(2) Uani 1 1 d . . . C14B C 0.53723(5) 0.90320(9) 0.60936(9) 0.0258(2) Uani 1 1 d . . . H2NB H 0.5654(6) 0.7107(12) 0.6922(11) 0.047(4) Uiso 1 1 d . . . H2B H 0.6588(5) 0.9675(10) 0.6018(9) 0.024(3) Uiso 1 1 d . . . H3B H 0.7314(5) 0.9208(9) 0.5159(8) 0.022(3) Uiso 1 1 d . . . H4B H 0.7470(5) 0.7373(9) 0.4818(8) 0.019(3) Uiso 1 1 d . . . H5B H 0.7283(5) 0.5347(9) 0.4936(8) 0.022(3) Uiso 1 1 d . . . H6B H 0.6725(5) 0.3975(10) 0.5420(9) 0.023(3) Uiso 1 1 d . . . H7B H 0.6018(5) 0.4366(10) 0.6282(9) 0.032(3) Uiso 1 1 d . . . H11D H 0.4942(5) 0.6177(10) 0.5588(9) 0.024(3) Uiso 1 1 d . . . H11E H 0.5031(5) 0.5096(10) 0.6202(9) 0.024(3) Uiso 1 1 d . . . H11F H 0.4791(5) 0.6114(10) 0.6717(9) 0.026(3) Uiso 1 1 d . . . H12D H 0.6256(6) 0.6021(10) 0.8284(9) 0.028(3) Uiso 1 1 d . . . H12E H 0.5868(5) 0.5009(11) 0.7944(9) 0.029(3) Uiso 1 1 d . . . H12F H 0.5579(5) 0.5989(10) 0.8347(9) 0.029(3) Uiso 1 1 d . . . H13D H 0.6275(5) 0.9617(11) 0.7656(9) 0.031(3) Uiso 1 1 d . . . H13E H 0.6467(6) 0.8501(11) 0.8138(10) 0.036(3) Uiso 1 1 d . . . H13F H 0.5858(5) 0.8884(10) 0.8163(9) 0.024(3) Uiso 1 1 d . . . H14D H 0.5486(5) 0.9773(11) 0.5965(10) 0.034(3) Uiso 1 1 d . . . H14E H 0.5224(5) 0.8640(11) 0.5443(10) 0.035(3) Uiso 1 1 d . . . H14F H 0.5089(6) 0.9089(11) 0.6476(10) 0.042(4) Uiso 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 0.02294(11) 0.02186(11) 0.02145(11) -0.00206(9) 0.00245(8) -0.00017(9) Cl2 0.02595(12) 0.03658(15) 0.02776(13) 0.00030(10) 0.00610(10) -0.00458(11) Cl3 0.02406(12) 0.02548(12) 0.02832(12) 0.00210(9) 0.00881(9) -0.00391(9) O1 0.0247(4) 0.0663(7) 0.0318(5) 0.0125(4) 0.0070(4) 0.0083(4) O2 0.0223(4) 0.0316(4) 0.0310(4) 0.0052(3) 0.0050(3) 0.0044(3) O3 0.0274(4) 0.0484(5) 0.0403(5) 0.0160(4) 0.0148(4) 0.0095(4) O4A 0.0300(7) 0.0382(8) 0.0268(7) -0.0007(6) 0.0088(5) 0.0043(6) O4B 0.0255(10) 0.0452(12) 0.0334(11) 0.0069(9) 0.0078(8) 0.0060(9) O5A 0.0296(10) 0.0488(13) 0.0278(9) -0.0034(10) 0.0049(7) -0.0051(10) O5B 0.0228(13) 0.061(2) 0.0295(13) -0.0040(17) 0.0056(9) -0.0021(16) O6 0.0249(4) 0.0392(5) 0.0380(5) -0.0014(4) 0.0069(4) 0.0021(3) N1A 0.0144(3) 0.0140(3) 0.0156(3) 0.0015(3) 0.0045(3) 0.0008(3) N2A 0.0152(3) 0.0147(4) 0.0144(3) -0.0011(3) 0.0036(3) -0.0016(3) C1A 0.0125(4) 0.0166(4) 0.0142(4) 0.0000(3) 0.0057(3) 0.0004(3) C2A 0.0175(4) 0.0158(4) 0.0195(4) -0.0020(3) 0.0070(3) -0.0010(3) C3A 0.0177(4) 0.0220(5) 0.0172(4) -0.0054(3) 0.0048(3) -0.0043(4) C4A 0.0147(4) 0.0268(5) 0.0139(4) -0.0003(3) 0.0034(3) -0.0011(3) C5A 0.0204(5) 0.0235(5) 0.0173(4) 0.0044(4) 0.0033(3) 0.0037(4) C6A 0.0278(5) 0.0175(5) 0.0254(5) 0.0057(4) 0.0050(4) 0.0034(4) C7A 0.0229(5) 0.0157(4) 0.0218(5) 0.0002(3) 0.0041(4) -0.0015(4) C8A 0.0145(4) 0.0165(4) 0.0150(4) 0.0005(3) 0.0040(3) -0.0001(3) C9A 0.0121(4) 0.0167(4) 0.0142(4) 0.0001(3) 0.0058(3) -0.0001(3) C10A 0.0148(4) 0.0202(4) 0.0139(4) 0.0013(3) 0.0058(3) 0.0005(3) C11A 0.0245(5) 0.0261(5) 0.0184(5) 0.0045(4) 0.0057(4) -0.0057(4) C12A 0.0160(4) 0.0221(5) 0.0283(5) -0.0029(4) 0.0039(4) 0.0043(4) C13A 0.0159(4) 0.0199(5) 0.0248(5) 0.0007(4) 0.0040(4) -0.0028(4) C14A 0.0275(5) 0.0241(5) 0.0172(4) -0.0024(4) 0.0077(4) 0.0028(4) N1B 0.0149(3) 0.0153(4) 0.0191(4) -0.0025(3) 0.0047(3) 0.0005(3) N2B 0.0153(4) 0.0165(4) 0.0193(4) -0.0005(3) 0.0075(3) -0.0010(3) C1B 0.0137(4) 0.0165(4) 0.0140(4) -0.0004(3) 0.0023(3) -0.0006(3) C2B 0.0202(4) 0.0147(4) 0.0209(4) 0.0005(3) 0.0039(3) -0.0015(3) C3B 0.0210(5) 0.0206(5) 0.0199(4) 0.0025(3) 0.0066(3) -0.0059(4) C4B 0.0163(4) 0.0234(5) 0.0161(4) 0.0003(3) 0.0056(3) -0.0030(3) C5B 0.0210(5) 0.0211(5) 0.0206(4) -0.0033(4) 0.0098(4) 0.0004(4) C6B 0.0275(5) 0.0154(5) 0.0313(5) -0.0051(4) 0.0141(4) 0.0003(4) C7B 0.0230(5) 0.0163(4) 0.0264(5) -0.0005(4) 0.0117(4) -0.0034(4) C8B 0.0148(4) 0.0175(4) 0.0166(4) -0.0015(3) 0.0062(3) -0.0009(3) C9B 0.0130(4) 0.0164(4) 0.0130(4) -0.0006(3) 0.0028(3) -0.0018(3) C10B 0.0144(4) 0.0199(4) 0.0131(4) -0.0008(3) 0.0039(3) -0.0014(3) C11B 0.0164(4) 0.0206(5) 0.0324(6) -0.0037(4) 0.0085(4) -0.0035(4) C12B 0.0307(6) 0.0279(6) 0.0210(5) 0.0042(4) 0.0121(4) 0.0067(4) C13B 0.0245(5) 0.0295(6) 0.0234(5) -0.0091(4) 0.0079(4) -0.0041(4) C14B 0.0180(5) 0.0236(5) 0.0341(6) 0.0011(4) 0.0041(4) 0.0047(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 H1OA 0.838(16) . ? O1 H1OB 0.838(17) . ? O2 H2OA 0.849(13) . ? O2 H2OB 0.839(17) . ? O3 H3OA 0.952(19) . ? O3 H3OB 0.928(18) . ? O3 H7O 1.27(2) . ? O4A O4B 1.486(3) . ? O4A H4O 1.09(2) . ? O4A H7O 1.22(2) . ? O4A H8O 1.20(3) . ? O4B H4O 1.29(2) . ? O4B H7O 1.46(2) . ? O4B H8O 1.31(3) . ? O5A O5B 0.633(3) . ? O5A H5OA 0.843(18) . ? O5A H5OB 0.93(3) . ? O5A H8O 1.35(3) . ? O5B H5OA 0.936(18) . ? O5B H5OB 0.82(3) . ? O5B H8O 1.29(3) . ? O6 H6OA 0.893(16) . ? O6 H6OB 0.853(19) . ? N1A C1A 1.4578(11) . ? N1A C11A 1.4761(12) . ? N1A C12A 1.4778(12) . ? N2A C8A 1.4735(11) . ? N2A C14A 1.4903(12) . ? N2A C13A 1.4933(12) . ? N2A H2NA 1.113(15) . ? C1A C2A 1.3736(12) . ? C1A C9A 1.4282(12) . ? C2A C3A 1.4081(13) . ? C2A H2A 0.933(11) . ? C3A C4A 1.3671(14) . ? C3A H3A 0.909(11) . ? C4A C10A 1.4198(13) . ? C4A H4A 0.944(11) . ? C5A C6A 1.3666(14) . ? C5A C10A 1.4182(13) . ? C5A H5A 0.941(11) . ? C6A C7A 1.4100(14) . ? C6A H6A 0.941(12) . ? C7A C8A 1.3665(13) . ? C7A H7A 0.951(12) . ? C8A C9A 1.4262(12) . ? C9A C10A 1.4286(12) . ? C11A H11A 0.974(12) . ? C11A H11B 0.924(13) . ? C11A H11C 0.966(12) . ? C12A H12A 0.979(12) . ? C12A H12B 0.922(13) . ? C12A H12C 0.956(12) . ? C13A H13A 1.009(11) . ? C13A H13B 0.967(12) . ? C13A H13C 0.997(12) . ? C14A H14A 0.995(12) . ? C14A H14B 0.957(12) . ? C14A H14C 0.947(12) . ? N1B C1B 1.4600(11) . ? N1B C13B 1.4739(12) . ? N1B C14B 1.4746(12) . ? N2B C8B 1.4729(11) . ? N2B C11B 1.4887(12) . ? N2B C12B 1.4914(13) . ? N2B H2NB 1.033(14) . ? C1B C2B 1.3666(13) . ? C1B C9B 1.4291(12) . ? C2B C3B 1.4119(13) . ? C2B H2B 0.941(12) . ? C3B C4B 1.3589(14) . ? C3B H3B 0.945(11) . ? C4B C10B 1.4182(13) . ? C4B H4B 0.924(11) . ? C5B C6B 1.3648(14) . ? C5B C10B 1.4133(13) . ? C5B H5B 0.963(11) . ? C6B C7B 1.4080(13) . ? C6B H6B 0.878(12) . ? C7B C8B 1.3634(13) . ? C7B H7B 0.892(12) . ? C8B C9B 1.4245(12) . ? C9B C10B 1.4329(12) . ? C11B H11D 0.984(12) . ? C11B H11E 0.933(12) . ? C11B H11F 0.952(12) . ? C12B H12D 0.974(12) . ? C12B H12E 0.912(13) . ? C12B H12F 0.942(12) . ? C13B H13D 0.915(13) . ? C13B H13E 0.936(13) . ? C13B H13F 0.948(11) . ? C14B H14D 0.949(13) . ? C14B H14E 0.956(13) . ? C14B H14F 0.933(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 H1OA O1 H1OB 110.2(15) . . ? H2OA O2 H2OB 111.2(13) . . ? H3OA O3 H3OB 105.7(14) . . ? H3OA O3 H7O 110.7(13) . . ? H3OB O3 H7O 111.8(13) . . ? O4B O4A H4O 57.7(11) . . ? O4B O4A H7O 64.6(9) . . ? H4O O4A H7O 96.5(13) . . ? O4B O4A H8O 57.0(12) . . ? H4O O4A H8O 94.0(15) . . ? H7O O4A H8O 100.2(14) . . ? O4A O4B H4O 45.6(9) . . ? O4A O4B H7O 48.9(8) . . ? H4O O4B H7O 77.4(11) . . ? O4A O4B H8O 50.4(11) . . ? H4O O4B H8O 80.4(13) . . ? H7O O4B H8O 84.0(13) . . ? O5B O5A H5OA 77.3(13) . . ? O5B O5A H5OB 59.9(17) . . ? H5OA O5A H5OB 107(2) . . ? O5B O5A H8O 71.3(12) . . ? H5OA O5A H8O 114.0(16) . . ? H5OB O5A H8O 104.2(19) . . ? O5A O5B H5OA 61.4(12) . . ? O5A O5B H5OB 78(2) . . ? H5OA O5B H5OB 109(2) . . ? O5A O5B H8O 81.1(12) . . ? H5OA O5B H8O 112.0(15) . . ? H5OB O5B H8O 117(2) . . ? H6OA O6 H6OB 105.3(15) . . ? C1A N1A C11A 111.92(7) . . ? C1A N1A C12A 112.22(7) . . ? C11A N1A C12A 111.57(8) . . ? C8A N2A C14A 112.00(7) . . ? C8A N2A C13A 112.87(7) . . ? C14A N2A C13A 111.68(8) . . ? C8A N2A H2NA 101.3(8) . . ? C14A N2A H2NA 109.9(8) . . ? C13A N2A H2NA 108.5(8) . . ? C2A C1A C9A 121.00(8) . . ? C2A C1A N1A 120.60(8) . . ? C9A C1A N1A 118.39(7) . . ? C1A C2A C3A 120.74(9) . . ? C1A C2A H2A 119.1(7) . . ? C3A C2A H2A 120.2(6) . . ? C4A C3A C2A 119.95(9) . . ? C4A C3A H3A 120.9(7) . . ? C2A C3A H3A 119.1(7) . . ? C3A C4A C10A 121.03(9) . . ? C3A C4A H4A 121.7(7) . . ? C10A C4A H4A 117.2(7) . . ? C6A C5A C10A 120.89(9) . . ? C6A C5A H5A 118.4(7) . . ? C10A C5A H5A 120.6(7) . . ? C5A C6A C7A 120.15(9) . . ? C5A C6A H6A 120.6(7) . . ? C7A C6A H6A 119.2(7) . . ? C8A C7A C6A 120.06(9) . . ? C8A C7A H7A 118.2(7) . . ? C6A C7A H7A 121.7(7) . . ? C7A C8A C9A 122.10(8) . . ? C7A C8A N2A 119.55(8) . . ? C9A C8A N2A 118.34(7) . . ? C8A C9A C1A 125.29(8) . . ? C8A C9A C10A 116.97(8) . . ? C1A C9A C10A 117.74(8) . . ? C5A C10A C4A 120.68(8) . . ? C5A C10A C9A 119.81(8) . . ? C4A C10A C9A 119.51(8) . . ? N1A C11A H11A 110.5(7) . . ? N1A C11A H11B 110.6(8) . . ? H11A C11A H11B 103.9(10) . . ? N1A C11A H11C 109.2(7) . . ? H11A C11A H11C 103.5(9) . . ? H11B C11A H11C 118.7(10) . . ? N1A C12A H12A 108.9(7) . . ? N1A C12A H12B 110.7(7) . . ? H12A C12A H12B 104.3(10) . . ? N1A C12A H12C 107.5(7) . . ? H12A C12A H12C 112.7(9) . . ? H12B C12A H12C 112.6(10) . . ? N2A C13A H13A 108.1(6) . . ? N2A C13A H13B 108.0(7) . . ? H13A C13A H13B 112.9(9) . . ? N2A C13A H13C 107.0(7) . . ? H13A C13A H13C 111.6(9) . . ? H13B C13A H13C 109.0(9) . . ? N2A C14A H14A 110.6(6) . . ? N2A C14A H14B 108.2(7) . . ? H14A C14A H14B 108.8(9) . . ? N2A C14A H14C 109.6(7) . . ? H14A C14A H14C 109.9(9) . . ? H14B C14A H14C 109.6(9) . . ? C1B N1B C13B 111.88(7) . . ? C1B N1B C14B 112.48(8) . . ? C13B N1B C14B 111.54(8) . . ? C8B N2B C11B 112.85(7) . . ? C8B N2B C12B 111.27(7) . . ? C11B N2B C12B 112.02(8) . . ? C8B N2B H2NB 104.0(8) . . ? C11B N2B H2NB 107.4(8) . . ? C12B N2B H2NB 108.8(8) . . ? C2B C1B C9B 121.07(8) . . ? C2B C1B N1B 120.80(8) . . ? C9B C1B N1B 118.12(7) . . ? C1B C2B C3B 120.83(9) . . ? C1B C2B H2B 121.5(7) . . ? C3B C2B H2B 117.6(7) . . ? C4B C3B C2B 119.82(9) . . ? C4B C3B H3B 118.9(7) . . ? C2B C3B H3B 121.2(7) . . ? C3B C4B C10B 121.42(9) . . ? C3B C4B H4B 120.0(7) . . ? C10B C4B H4B 118.6(7) . . ? C6B C5B C10B 121.11(9) . . ? C6B C5B H5B 118.4(7) . . ? C10B C5B H5B 120.5(7) . . ? C5B C6B C7B 119.88(9) . . ? C5B C6B H6B 121.4(7) . . ? C7B C6B H6B 118.8(7) . . ? C8B C7B C6B 120.24(9) . . ? C8B C7B H7B 119.3(8) . . ? C6B C7B H7B 120.5(8) . . ? C7B C8B C9B 122.30(8) . . ? C7B C8B N2B 119.69(8) . . ? C9B C8B N2B 118.00(8) . . ? C8B C9B C1B 125.82(8) . . ? C8B C9B C10B 116.55(8) . . ? C1B C9B C10B 117.61(8) . . ? C5B C10B C4B 120.86(8) . . ? C5B C10B C9B 119.90(8) . . ? C4B C10B C9B 119.24(8) . . ? N2B C11B H11D 109.9(7) . . ? N2B C11B H11E 111.4(7) . . ? H11D C11B H11E 103.4(9) . . ? N2B C11B H11F 106.6(7) . . ? H11D C11B H11F 113.6(10) . . ? H11E C11B H11F 112.1(10) . . ? N2B C12B H12D 108.0(7) . . ? N2B C12B H12E 110.3(7) . . ? H12D C12B H12E 105.5(10) . . ? N2B C12B H12F 110.1(7) . . ? H12D C12B H12F 113.5(10) . . ? H12E C12B H12F 109.3(10) . . ? N1B C13B H13D 110.5(8) . . ? N1B C13B H13E 109.9(8) . . ? H13D C13B H13E 107.1(11) . . ? N1B C13B H13F 107.7(7) . . ? H13D C13B H13F 115.9(10) . . ? H13E C13B H13F 105.5(10) . . ? N1B C14B H14D 112.9(8) . . ? N1B C14B H14E 107.4(7) . . ? H14D C14B H14E 110.1(10) . . ? N1B C14B H14F 106.6(8) . . ? H14D C14B H14F 107.5(11) . . ? H14E C14B H14F 112.4(11) . . ? 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 C11A N1A C1A C2A -61.79(10) . . . . ? C12A N1A C1A C2A 64.54(10) . . . . ? C11A N1A C1A C9A 117.64(9) . . . . ? C12A N1A C1A C9A -116.02(9) . . . . ? C9A C1A C2A C3A -1.20(13) . . . . ? N1A C1A C2A C3A 178.22(8) . . . . ? C1A C2A C3A C4A -0.06(14) . . . . ? C2A C3A C4A C10A 0.81(14) . . . . ? C10A C5A C6A C7A -1.48(15) . . . . ? C5A C6A C7A C8A 0.49(15) . . . . ? C6A C7A C8A C9A 0.90(14) . . . . ? C6A C7A C8A N2A -178.62(8) . . . . ? C14A N2A C8A C7A 61.14(11) . . . . ? C13A N2A C8A C7A -65.92(11) . . . . ? C14A N2A C8A C9A -118.39(9) . . . . ? C13A N2A C8A C9A 114.54(9) . . . . ? C7A C8A C9A C1A 179.48(8) . . . . ? N2A C8A C9A C1A -0.99(12) . . . . ? C7A C8A C9A C10A -1.25(13) . . . . ? N2A C8A C9A C10A 178.28(7) . . . . ? C2A C1A C9A C8A -179.08(8) . . . . ? N1A C1A C9A C8A 1.49(12) . . . . ? C2A C1A C9A C10A 1.65(12) . . . . ? N1A C1A C9A C10A -177.78(7) . . . . ? C6A C5A C10A C4A -178.42(9) . . . . ? C6A C5A C10A C9A 1.09(14) . . . . ? C3A C4A C10A C5A 179.21(9) . . . . ? C3A C4A C10A C9A -0.31(13) . . . . ? C8A C9A C10A C5A 0.25(12) . . . . ? C1A C9A C10A C5A 179.58(8) . . . . ? C8A C9A C10A C4A 179.77(8) . . . . ? C1A C9A C10A C4A -0.90(12) . . . . ? C13B N1B C1B C2B -62.28(11) . . . . ? C14B N1B C1B C2B 64.19(11) . . . . ? C13B N1B C1B C9B 116.77(9) . . . . ? C14B N1B C1B C9B -116.76(9) . . . . ? C9B C1B C2B C3B -0.64(13) . . . . ? N1B C1B C2B C3B 178.38(8) . . . . ? C1B C2B C3B C4B 0.68(14) . . . . ? C2B C3B C4B C10B -0.57(14) . . . . ? C10B C5B C6B C7B -0.59(15) . . . . ? C5B C6B C7B C8B -0.32(16) . . . . ? C6B C7B C8B C9B 1.31(15) . . . . ? C6B C7B C8B N2B -177.27(9) . . . . ? C11B N2B C8B C7B -63.16(11) . . . . ? C12B N2B C8B C7B 63.76(11) . . . . ? C11B N2B C8B C9B 118.20(9) . . . . ? C12B N2B C8B C9B -114.88(9) . . . . ? C7B C8B C9B C1B -179.83(9) . . . . ? N2B C8B C9B C1B -1.23(13) . . . . ? C7B C8B C9B C10B -1.32(13) . . . . ? N2B C8B C9B C10B 177.28(7) . . . . ? C2B C1B C9B C8B 178.97(9) . . . . ? N1B C1B C9B C8B -0.08(12) . . . . ? C2B C1B C9B C10B 0.48(12) . . . . ? N1B C1B C9B C10B -178.57(7) . . . . ? C6B C5B C10B C4B 179.90(9) . . . . ? C6B C5B C10B C9B 0.53(14) . . . . ? C3B C4B C10B C5B -178.96(9) . . . . ? C3B C4B C10B C9B 0.42(13) . . . . ? C8B C9B C10B C5B 0.40(12) . . . . ? C1B C9B C10B C5B 179.03(8) . . . . ? C8B C9B C10B C4B -178.99(8) . . . . ? C1B C9B C10B C4B -0.35(12) . . . . ? 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 H2OA O1 0.849(13) 1.860(14) 2.7003(13) 170.0(12) . O3 H3OA O2 0.952(19) 1.620(19) 2.5608(11) 168.8(16) . O4A H7O O3 1.22(2) 1.27(2) 2.3764(16) 144.6(16) . O4A H8O O5A 1.20(3) 1.35(3) 2.528(3) 166(2) . O5B H8O O4B 1.29(3) 1.31(3) 2.496(4) 148(2) . O5A H5OA O6 0.843(18) 1.853(18) 2.669(3) 162.6(18) . O5B H5OA O6 0.936(18) 1.853(18) 2.733(4) 155.6(17) . O1 H1OA Cl1 0.838(16) 2.313(17) 3.1491(10) 175.2(14) 4_565 O1 H1OB Cl2 0.838(17) 2.385(18) 3.2205(10) 175.1(14) 4_565 O4A H4O Cl2 1.09(2) 1.98(2) 2.9913(13) 152.0(16) 4_565 O5B H5OB Cl3 0.82(3) 2.20(3) 3.003(4) 166(3) 4_565 O2 H2OB Cl1 0.839(17) 2.228(17) 3.0635(9) 173.6(14) . O6 H6OA Cl2 0.893(16) 2.340(16) 3.2086(9) 164.2(13) . O6 H6OB Cl3 0.853(19) 2.32(2) 3.1681(9) 172.4(17) . N2A H2NA N1A 1.113(15) 1.521(15) 2.5872(10) 158.1(13) . N2B H2NB N1B 1.033(14) 1.617(14) 2.5905(11) 155.2(12) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 39.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.560 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.053 data_4 _database_code_depnum_ccdc_archive 'CCDC 622713' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H38 Cl3 N4 O6' _chemical_formula_weight 632.97 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.1816(3) _cell_length_b 11.8826(3) _cell_length_c 22.3500(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3500.72(14) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1332 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 KM4CCD _diffrn_measurement_method 'omeg ascan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 63320 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6150 _reflns_number_gt 5518 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET) (compiled Nov 11 2005,15:50:43) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXTL-97 _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^)+(0.1196P)^2^+3.0706P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(8) _refine_ls_number_reflns 6150 _refine_ls_number_parameters 399 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1746 _refine_ls_wR_factor_gt 0.1687 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.063 _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 0.28643(9) 0.21320(9) 0.35788(5) 0.0348(3) Uani 1 1 d . . . Cl2 Cl 0.40147(11) 0.15637(13) 0.59039(7) 0.0499(4) Uani 1 1 d . . . Cl3 Cl 0.51665(8) 0.27096(9) 0.82095(5) 0.0333(3) Uani 1 1 d . . . O1 O -0.0411(4) 0.2750(4) 0.45669(18) 0.0597(12) Uani 1 1 d . . . O2 O 0.1557(3) 0.3294(3) 0.45054(17) 0.0509(10) Uani 1 1 d . . . O3 O 0.2351(4) 0.3257(4) 0.5566(2) 0.0685(14) Uani 1 1 d . . . O4A O 0.1143(6) 0.3411(6) 0.6323(4) 0.0626(19) Uani 0.60 1 d P . . O4B O 0.0950(8) 0.2245(9) 0.6198(5) 0.057(3) Uani 0.40 1 d P . . O5A O 0.1603(10) 0.2014(6) 0.7149(5) 0.052(2) Uani 0.60 1 d PU . . O5B O 0.1594(13) 0.2517(12) 0.7224(7) 0.054(3) Uani 0.40 1 d PU . . O6 O 0.3566(3) 0.1734(3) 0.72897(16) 0.0504(10) Uani 1 1 d . . . N1A N 0.2554(2) 0.6610(3) 0.42570(14) 0.0166(7) Uani 1 1 d . . . N2A N 0.2763(2) 0.8744(3) 0.40645(15) 0.0168(7) Uani 1 1 d . . . H2NA H 0.2849 0.8072 0.4056 0.020 Uiso 1 1 calc R . . C1A C 0.1758(3) 0.6852(3) 0.46909(16) 0.0154(8) Uani 1 1 d . . . C2A C 0.1278(3) 0.5999(3) 0.49861(18) 0.0194(8) Uani 1 1 d . . . H2A H 0.1442 0.5238 0.4897 0.023 Uiso 1 1 calc R . . C3A C 0.0539(3) 0.6245(4) 0.54239(19) 0.0231(9) Uani 1 1 d . . . H3A H 0.0207 0.5651 0.5630 0.028 Uiso 1 1 calc R . . C4A C 0.0303(3) 0.7329(3) 0.55490(18) 0.0188(8) Uani 1 1 d . . . H4A H -0.0195 0.7483 0.5845 0.023 Uiso 1 1 calc R . . C5A C 0.0520(3) 0.9375(3) 0.53859(18) 0.0213(8) Uani 1 1 d . . . H5A H 0.0032 0.9529 0.5688 0.026 Uiso 1 1 calc R . . C6A C 0.0962(3) 1.0233(3) 0.5088(2) 0.0254(9) Uani 1 1 d . . . H6A H 0.0776 1.0986 0.5181 0.031 Uiso 1 1 calc R . . C7A C 0.1695(3) 1.0032(3) 0.46418(19) 0.0231(9) Uani 1 1 d . . . H7A H 0.1995 1.0641 0.4431 0.028 Uiso 1 1 calc R . . C8A C 0.1965(3) 0.8951(3) 0.45173(17) 0.0175(8) Uani 1 1 d . . . C9A C 0.1524(3) 0.8018(3) 0.48074(16) 0.0143(7) Uani 1 1 d . . . C10A C 0.0779(3) 0.8242(3) 0.52509(17) 0.0182(8) Uani 1 1 d . . . C11A C 0.3436(3) 0.6071(4) 0.4540(2) 0.0255(9) Uani 1 1 d . . . H11A H 0.3584 0.6446 0.4920 0.038 Uiso 1 1 calc R . . H11B H 0.4025 0.6134 0.4274 0.038 Uiso 1 1 calc R . . H11C H 0.3286 0.5275 0.4613 0.038 Uiso 1 1 calc R . . C12A C 0.2184(4) 0.5954(3) 0.37372(18) 0.0254(9) Uani 1 1 d . . . H12A H 0.2033 0.5182 0.3864 0.038 Uiso 1 1 calc R . . H12B H 0.2707 0.5941 0.3426 0.038 Uiso 1 1 calc R . . H12C H 0.1567 0.6304 0.3579 0.038 Uiso 1 1 calc R . . C13A C 0.2446(3) 0.9080(3) 0.34467(18) 0.0253(9) Uani 1 1 d . . . H13A H 0.1798 0.8721 0.3349 0.038 Uiso 1 1 calc R . . H13B H 0.2964 0.8839 0.3159 0.038 Uiso 1 1 calc R . . H13C H 0.2370 0.9900 0.3428 0.038 Uiso 1 1 calc R . . C14A C 0.3749(3) 0.9247(4) 0.4237(2) 0.0266(9) Uani 1 1 d . . . H14A H 0.3712 1.0067 0.4196 0.040 Uiso 1 1 calc R . . H14B H 0.4284 0.8954 0.3976 0.040 Uiso 1 1 calc R . . H14C H 0.3903 0.9053 0.4653 0.040 Uiso 1 1 calc R . . N1B N 0.4968(2) 0.8396(3) 0.75318(14) 0.0164(6) Uani 1 1 d . . . N2B N 0.5247(2) 0.6276(3) 0.77453(14) 0.0173(7) Uani 1 1 d . . . H2NB H 0.5312 0.7171 0.7761 0.021 Uiso 1 1 calc R . . C1B C 0.4212(3) 0.8085(3) 0.70779(17) 0.0155(7) Uani 1 1 d . . . C2B C 0.3733(3) 0.8906(3) 0.67525(17) 0.0200(8) Uani 1 1 d . . . H2B H 0.3884 0.9675 0.6825 0.024 Uiso 1 1 calc R . . C3B C 0.3021(3) 0.8617(3) 0.63135(18) 0.0203(8) Uani 1 1 d . . . H3B H 0.2706 0.9192 0.6084 0.024 Uiso 1 1 calc R . . C4B C 0.2774(3) 0.7512(3) 0.62119(18) 0.0187(8) Uani 1 1 d . . . H4B H 0.2281 0.7328 0.5917 0.022 Uiso 1 1 calc R . . C5B C 0.3020(3) 0.5511(3) 0.64313(18) 0.0216(8) Uani 1 1 d . . . H5B H 0.2541 0.5331 0.6129 0.026 Uiso 1 1 calc R . . C6B C 0.3474(3) 0.4666(3) 0.67487(18) 0.0246(9) Uani 1 1 d . . . H6B H 0.3291 0.3905 0.6675 0.029 Uiso 1 1 calc R . . C7B C 0.4205(3) 0.4919(3) 0.71811(18) 0.0217(8) Uani 1 1 d . . . H7B H 0.4530 0.4329 0.7394 0.026 Uiso 1 1 calc R . . C8B C 0.4452(3) 0.6014(3) 0.72984(17) 0.0158(7) Uani 1 1 d . . . C9B C 0.3989(3) 0.6926(3) 0.69891(16) 0.0150(7) Uani 1 1 d . . . C10B C 0.3253(3) 0.6634(3) 0.65467(17) 0.0176(8) Uani 1 1 d . . . C11B C 0.4975(3) 0.5903(3) 0.83533(17) 0.0219(9) Uani 1 1 d . . . H11D H 0.4300 0.6191 0.8457 0.033 Uiso 1 1 calc R . . H11E H 0.5474 0.6191 0.8640 0.033 Uiso 1 1 calc R . . H11F H 0.4968 0.5079 0.8368 0.033 Uiso 1 1 calc R . . C12B C 0.6257(3) 0.5834(4) 0.7552(2) 0.0256(9) Uani 1 1 d . . . H12D H 0.6226 0.5012 0.7520 0.038 Uiso 1 1 calc R . . H12E H 0.6772 0.6045 0.7848 0.038 Uiso 1 1 calc R . . H12F H 0.6436 0.6156 0.7163 0.038 Uiso 1 1 calc R . . C13B C 0.5833(3) 0.9009(3) 0.7263(2) 0.0264(9) Uani 1 1 d . . . H13D H 0.6109 0.8571 0.6929 0.040 Uiso 1 1 calc R . . H13E H 0.6362 0.9118 0.7566 0.040 Uiso 1 1 calc R . . H13F H 0.5602 0.9743 0.7117 0.040 Uiso 1 1 calc R . . C14B C 0.4520(4) 0.9013(4) 0.80345(19) 0.0282(9) Uani 1 1 d . . . H14D H 0.4282 0.9750 0.7896 0.042 Uiso 1 1 calc R . . H14E H 0.5031 0.9117 0.8348 0.042 Uiso 1 1 calc R . . H14F H 0.3946 0.8585 0.8196 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0408(6) 0.0265(5) 0.0371(6) 0.0037(5) 0.0045(5) -0.0080(5) Cl2 0.0515(8) 0.0558(8) 0.0424(6) 0.0039(6) 0.0026(6) 0.0038(6) Cl3 0.0331(6) 0.0272(5) 0.0396(6) 0.0031(5) -0.0083(5) 0.0061(4) O1 0.064(3) 0.082(3) 0.034(2) -0.007(2) -0.0048(19) 0.020(2) O2 0.081(3) 0.0340(19) 0.0379(19) -0.0031(16) -0.007(2) 0.0089(19) O3 0.079(3) 0.067(3) 0.060(3) -0.019(2) -0.032(2) 0.020(2) O4A 0.049(4) 0.056(4) 0.083(5) 0.004(4) -0.013(4) -0.005(3) O4B 0.055(7) 0.065(7) 0.050(6) -0.019(5) -0.010(5) 0.016(5) O5A 0.079(5) 0.035(5) 0.043(4) -0.006(4) 0.002(4) -0.003(5) O5B 0.053(5) 0.068(9) 0.042(6) -0.002(7) 0.008(5) 0.004(8) O6 0.079(3) 0.039(2) 0.0336(18) 0.0011(16) -0.0075(19) -0.0072(19) N1A 0.0179(16) 0.0114(14) 0.0204(17) -0.0014(12) -0.0007(13) 0.0043(13) N2A 0.0169(16) 0.0112(15) 0.0224(17) 0.0029(12) 0.0046(13) 0.0015(12) C1A 0.0169(19) 0.0126(17) 0.0167(18) 0.0011(14) -0.0074(14) -0.0015(14) C2A 0.0161(18) 0.0166(18) 0.025(2) -0.0004(15) -0.0011(16) 0.0004(15) C3A 0.0169(19) 0.027(2) 0.026(2) 0.0054(17) -0.0012(16) -0.0083(17) C4A 0.0104(18) 0.028(2) 0.018(2) 0.0017(15) 0.0019(14) 0.0006(15) C5A 0.0171(19) 0.024(2) 0.023(2) -0.0053(16) -0.0003(15) 0.0039(17) C6A 0.025(2) 0.0166(19) 0.035(2) -0.0036(17) 0.0015(18) 0.0055(16) C7A 0.023(2) 0.0155(19) 0.031(2) 0.0021(16) -0.0028(17) 0.0008(15) C8A 0.0143(17) 0.0174(19) 0.0208(19) 0.0021(15) -0.0004(15) 0.0013(14) C9A 0.0093(17) 0.0157(18) 0.0179(18) -0.0007(14) -0.0054(14) 0.0021(14) C10A 0.0152(19) 0.0179(19) 0.0215(19) -0.0012(15) -0.0035(15) 0.0019(15) C11A 0.020(2) 0.026(2) 0.030(2) 0.0077(17) -0.0011(17) 0.0054(16) C12A 0.038(2) 0.0234(19) 0.015(2) -0.0050(15) 0.0003(17) -0.0032(18) C13A 0.030(2) 0.0206(19) 0.025(2) 0.0057(16) -0.0008(17) 0.0020(17) C14A 0.0178(19) 0.025(2) 0.037(2) -0.0040(18) 0.0058(18) -0.0055(16) N1B 0.0188(16) 0.0142(15) 0.0162(15) -0.0005(12) -0.0014(13) -0.0008(13) N2B 0.0162(16) 0.0162(16) 0.0194(17) -0.0019(13) -0.0034(13) 0.0008(12) C1B 0.0139(18) 0.0133(16) 0.0194(19) -0.0026(14) 0.0035(14) 0.0014(14) C2B 0.026(2) 0.0130(17) 0.0212(19) 0.0032(15) 0.0017(16) 0.0057(16) C3B 0.0162(19) 0.0211(19) 0.024(2) 0.0087(16) 0.0017(15) 0.0044(16) C4B 0.017(2) 0.0218(19) 0.017(2) 0.0049(15) 0.0027(14) 0.0025(15) C5B 0.0195(19) 0.023(2) 0.023(2) -0.0018(16) -0.0025(16) -0.0042(16) C6B 0.029(2) 0.0163(18) 0.029(2) 0.0005(16) -0.0056(17) -0.0056(17) C7B 0.022(2) 0.0199(19) 0.023(2) 0.0032(15) -0.0054(16) 0.0018(16) C8B 0.0155(18) 0.0144(17) 0.0176(18) 0.0017(14) -0.0008(15) -0.0017(14) C9B 0.0149(18) 0.0153(17) 0.0149(18) 0.0002(14) 0.0039(15) 0.0007(14) C10B 0.0115(18) 0.0203(19) 0.0210(19) 0.0033(15) -0.0001(15) 0.0018(14) C11B 0.026(2) 0.0202(18) 0.019(2) 0.0048(15) -0.0036(16) -0.0038(16) C12B 0.0149(19) 0.025(2) 0.037(2) -0.0037(18) -0.0006(17) 0.0028(16) C13B 0.025(2) 0.023(2) 0.031(2) 0.0068(18) -0.0023(18) -0.0114(17) C14B 0.035(2) 0.024(2) 0.026(2) -0.0045(16) -0.0031(18) 0.0040(18) _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 O4A O4B 1.435(13) . ? O5A O5B 0.621(13) . ? N1A C1A 1.457(5) . ? N1A C11A 1.470(5) . ? N1A C12A 1.482(5) . ? N2A C8A 1.480(5) . ? N2A C14A 1.482(5) . ? N2A C13A 1.497(5) . ? N2A H2NA 0.8063 . ? C1A C2A 1.365(5) . ? C1A C9A 1.443(5) . ? C2A C3A 1.412(6) . ? C2A H2A 0.9500 . ? C3A C4A 1.354(6) . ? C3A H3A 0.9500 . ? C4A C10A 1.419(6) . ? C4A H4A 0.9500 . ? C5A C6A 1.350(6) . ? C5A C10A 1.421(5) . ? C5A H5A 0.9500 . ? C6A C7A 1.408(6) . ? C6A H6A 0.9500 . ? C7A C8A 1.362(5) . ? C7A H7A 0.9500 . ? C8A C9A 1.409(5) . ? C9A C10A 1.420(5) . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? N1B C14B 1.467(5) . ? N1B C1B 1.469(5) . ? N1B C13B 1.480(5) . ? N2B C11B 1.474(5) . ? N2B C8B 1.481(5) . ? N2B C12B 1.495(5) . ? N2B H2NB 1.0676 . ? C1B C2B 1.371(5) . ? C1B C9B 1.421(5) . ? C2B C3B 1.400(6) . ? C2B H2B 0.9500 . ? C3B C4B 1.372(6) . ? C3B H3B 0.9500 . ? C4B C10B 1.431(5) . ? C4B H4B 0.9500 . ? C5B C6B 1.368(6) . ? C5B C10B 1.393(6) . ? C5B H5B 0.9500 . ? C6B C7B 1.397(6) . ? C6B H6B 0.9500 . ? C7B C8B 1.367(5) . ? C7B H7B 0.9500 . ? C8B C9B 1.424(5) . ? C9B C10B 1.428(5) . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 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 C1A N1A C11A 111.7(3) . . ? C1A N1A C12A 112.9(3) . . ? C11A N1A C12A 111.6(3) . . ? C8A N2A C14A 112.2(3) . . ? C8A N2A C13A 112.8(3) . . ? C14A N2A C13A 112.1(3) . . ? C8A N2A H2NA 106.4 . . ? C14A N2A H2NA 106.4 . . ? C13A N2A H2NA 106.4 . . ? C2A C1A C9A 121.8(4) . . ? C2A C1A N1A 120.6(3) . . ? C9A C1A N1A 117.6(3) . . ? C1A C2A C3A 120.1(4) . . ? C1A C2A H2A 120.0 . . ? C3A C2A H2A 120.0 . . ? C4A C3A C2A 119.9(4) . . ? C4A C3A H3A 120.0 . . ? C2A C3A H3A 120.0 . . ? C3A C4A C10A 121.9(4) . . ? C3A C4A H4A 119.0 . . ? C10A C4A H4A 119.0 . . ? C6A C5A C10A 120.5(4) . . ? C6A C5A H5A 119.8 . . ? C10A C5A H5A 119.8 . . ? C5A C6A C7A 121.1(4) . . ? C5A C6A H6A 119.4 . . ? C7A C6A H6A 119.4 . . ? C8A C7A C6A 118.9(4) . . ? C8A C7A H7A 120.5 . . ? C6A C7A H7A 120.5 . . ? C7A C8A C9A 122.7(4) . . ? C7A C8A N2A 118.8(3) . . ? C9A C8A N2A 118.5(3) . . ? C8A C9A C10A 117.3(3) . . ? C8A C9A C1A 125.7(3) . . ? C10A C9A C1A 117.0(3) . . ? C4A C10A C9A 119.3(3) . . ? C4A C10A C5A 121.2(4) . . ? C9A C10A C5A 119.5(4) . . ? N1A C11A H11A 109.5 . . ? N1A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? N1A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? N1A C12A H12A 109.5 . . ? N1A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? N1A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? N2A C13A H13A 109.5 . . ? N2A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? N2A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? N2A C14A H14A 109.5 . . ? N2A C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? N2A C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? C14B N1B C1B 112.4(3) . . ? C14B N1B C13B 112.0(3) . . ? C1B N1B C13B 111.5(3) . . ? C11B N2B C8B 112.7(3) . . ? C11B N2B C12B 112.2(3) . . ? C8B N2B C12B 111.2(3) . . ? C11B N2B H2NB 106.8 . . ? C8B N2B H2NB 106.8 . . ? C12B N2B H2NB 106.8 . . ? C2B C1B C9B 121.3(4) . . ? C2B C1B N1B 120.0(3) . . ? C9B C1B N1B 118.7(3) . . ? C1B C2B C3B 120.4(4) . . ? C1B C2B H2B 119.8 . . ? C3B C2B H2B 119.8 . . ? C4B C3B C2B 120.6(4) . . ? C4B C3B H3B 119.7 . . ? C2B C3B H3B 119.7 . . ? C3B C4B C10B 120.4(4) . . ? C3B C4B H4B 119.8 . . ? C10B C4B H4B 119.8 . . ? C6B C5B C10B 120.7(4) . . ? C6B C5B H5B 119.6 . . ? C10B C5B H5B 119.6 . . ? C5B C6B C7B 120.1(4) . . ? C5B C6B H6B 119.9 . . ? C7B C6B H6B 119.9 . . ? C8B C7B C6B 120.2(4) . . ? C8B C7B H7B 119.9 . . ? C6B C7B H7B 119.9 . . ? C7B C8B C9B 122.0(4) . . ? C7B C8B N2B 119.9(3) . . ? C9B C8B N2B 118.1(3) . . ? C1B C9B C8B 125.5(3) . . ? C1B C9B C10B 118.2(3) . . ? C8B C9B C10B 116.3(3) . . ? C5B C10B C9B 120.7(3) . . ? C5B C10B C4B 120.2(4) . . ? C9B C10B C4B 119.0(4) . . ? N2B C11B H11D 109.5 . . ? N2B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? N2B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? N2B C12B H12D 109.5 . . ? N2B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? N2B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? N1B C13B H13D 109.5 . . ? N1B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? N1B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? N1B C14B H14D 109.5 . . ? N1B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? N1B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 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 C11A N1A C1A C2A -63.9(4) . . . . ? C12A N1A C1A C2A 62.8(4) . . . . ? C11A N1A C1A C9A 114.3(4) . . . . ? C12A N1A C1A C9A -119.0(4) . . . . ? C9A C1A C2A C3A -0.8(6) . . . . ? N1A C1A C2A C3A 177.3(3) . . . . ? C1A C2A C3A C4A 0.3(6) . . . . ? C2A C3A C4A C10A 0.1(6) . . . . ? C10A C5A C6A C7A -0.6(6) . . . . ? C5A C6A C7A C8A -0.8(6) . . . . ? C6A C7A C8A C9A 1.5(6) . . . . ? C6A C7A C8A N2A -177.7(4) . . . . ? C14A N2A C8A C7A 61.5(5) . . . . ? C13A N2A C8A C7A -66.4(5) . . . . ? C14A N2A C8A C9A -117.8(4) . . . . ? C13A N2A C8A C9A 114.4(4) . . . . ? C7A C8A C9A C10A -0.9(6) . . . . ? N2A C8A C9A C10A 178.4(3) . . . . ? C7A C8A C9A C1A 178.8(4) . . . . ? N2A C8A C9A C1A -2.0(5) . . . . ? C2A C1A C9A C8A -178.7(4) . . . . ? N1A C1A C9A C8A 3.1(5) . . . . ? C2A C1A C9A C10A 0.9(5) . . . . ? N1A C1A C9A C10A -177.2(3) . . . . ? C3A C4A C10A C9A 0.1(6) . . . . ? C3A C4A C10A C5A 179.7(4) . . . . ? C8A C9A C10A C4A 179.1(3) . . . . ? C1A C9A C10A C4A -0.6(5) . . . . ? C8A C9A C10A C5A -0.5(5) . . . . ? C1A C9A C10A C5A 179.8(3) . . . . ? C6A C5A C10A C4A -178.4(4) . . . . ? C6A C5A C10A C9A 1.2(6) . . . . ? C14B N1B C1B C2B 66.0(5) . . . . ? C13B N1B C1B C2B -60.8(4) . . . . ? C14B N1B C1B C9B -113.6(4) . . . . ? C13B N1B C1B C9B 119.6(4) . . . . ? C9B C1B C2B C3B -1.3(6) . . . . ? N1B C1B C2B C3B 179.2(3) . . . . ? C1B C2B C3B C4B 1.6(6) . . . . ? C2B C3B C4B C10B -1.1(6) . . . . ? C10B C5B C6B C7B -2.1(6) . . . . ? C5B C6B C7B C8B 1.5(6) . . . . ? C6B C7B C8B C9B -0.3(6) . . . . ? C6B C7B C8B N2B -178.3(4) . . . . ? C11B N2B C8B C7B -63.3(5) . . . . ? C12B N2B C8B C7B 63.8(5) . . . . ? C11B N2B C8B C9B 118.6(4) . . . . ? C12B N2B C8B C9B -114.3(4) . . . . ? C2B C1B C9B C8B 179.2(4) . . . . ? N1B C1B C9B C8B -1.2(5) . . . . ? C2B C1B C9B C10B 0.5(5) . . . . ? N1B C1B C9B C10B -180.0(3) . . . . ? C7B C8B C9B C1B -179.1(4) . . . . ? N2B C8B C9B C1B -1.0(6) . . . . ? C7B C8B C9B C10B -0.3(5) . . . . ? N2B C8B C9B C10B 177.8(3) . . . . ? C6B C5B C10B C9B 1.5(6) . . . . ? C6B C5B C10B C4B -180.0(4) . . . . ? C1B C9B C10B C5B 178.6(3) . . . . ? C8B C9B C10B C5B -0.3(5) . . . . ? C1B C9B C10B C4B 0.0(5) . . . . ? C8B C9B C10B C4B -178.8(3) . . . . ? C3B C4B C10B C5B -178.3(4) . . . . ? C3B C4B C10B C9B 0.3(6) . . . . ? 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 N2A H2NA N1A 0.81 1.84 2.586(5) 154.2 . N2B H2NB N1B 1.07 1.61 2.590(4) 150.3 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.362 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.107 #=END