# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d12336 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N2 O6' _chemical_formula_sum 'C22 H24 N2 O6' _chemical_formula_weight 412.43 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9679(3) _cell_length_b 19.0540(9) _cell_length_c 7.6683(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.428(2) _cell_angle_gamma 90.00 _cell_volume 1016.27(8) _cell_formula_units_Z 2 _cell_measurement_temperature 147(2) _cell_measurement_reflns_used 9970 _cell_measurement_theta_min 4.64 _cell_measurement_theta_max 66.30 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.819 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6930 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 147(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker ImuS' _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_measurement_device_type 'Bruker Kaapa APEX-DUO CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12698 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.64 _diffrn_reflns_theta_max 66.31 _reflns_number_total 3412 _reflns_number_gt 3391 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0402P)^2^+0.2123P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.16(14) # Hooft parameter 0.13(5) _refine_ls_number_reflns 3412 _refine_ls_number_parameters 283 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 O1 O 0.44557(19) 0.32207(6) 0.52025(17) 0.0384(3) Uani 1 1 d . . . O2 O 0.67708(17) 0.66301(7) 1.06590(17) 0.0371(3) Uani 1 1 d . . . O3 O 0.3030(3) 0.55543(8) 0.7322(3) 0.0784(6) Uani 1 1 d . . . O4 O 0.49704(16) 0.63887(6) 0.64998(15) 0.0309(3) Uani 1 1 d . . . O5 O 0.5173(3) 0.47828(8) 1.0189(3) 0.0901(8) Uani 1 1 d . . . O6 O 0.58607(15) 0.38573(6) 0.86093(13) 0.0262(2) Uani 1 1 d . . . N1 N 0.5003(2) 0.45816(7) 0.53735(16) 0.0268(3) Uani 1 1 d . . . N2 N 0.78159(19) 0.55679(7) 0.88089(16) 0.0260(3) Uani 1 1 d . . . C1 C 0.5994(3) 0.52035(8) 0.6119(2) 0.0287(4) Uani 1 1 d . . . C2 C 0.7246(2) 0.49445(8) 0.7780(2) 0.0274(3) Uani 1 1 d . . . C3 C 0.3520(2) 0.46553(8) 0.4325(2) 0.0291(3) Uani 1 1 d . . . H3A H 0.3110 0.5115 0.4003 0.035 Uiso 1 1 calc R . . C4 C 0.2443(2) 0.40577(8) 0.36109(19) 0.0255(3) Uani 1 1 d . . . C5 C 0.2954(2) 0.33666(9) 0.40579(19) 0.0274(3) Uani 1 1 d . . . C6 C 0.1909(3) 0.28037(9) 0.3314(2) 0.0336(4) Uani 1 1 d . . . H6A H 0.2265 0.2335 0.3607 0.040 Uiso 1 1 calc R . . C7 C 0.0364(2) 0.29316(11) 0.2158(2) 0.0364(4) Uani 1 1 d . . . H7A H -0.0322 0.2548 0.1631 0.044 Uiso 1 1 calc R . . C8 C -0.0206(3) 0.36106(11) 0.1750(2) 0.0429(5) Uani 1 1 d . . . H8A H -0.1303 0.3693 0.0981 0.051 Uiso 1 1 calc R . . C9 C 0.0831(3) 0.41673(10) 0.2467(2) 0.0368(4) Uani 1 1 d . . . H9A H 0.0443 0.4633 0.2180 0.044 Uiso 1 1 calc R . . C10 C 0.7250(3) 0.55314(10) 0.4761(2) 0.0378(4) Uani 1 1 d . . . H10A H 0.6428 0.5754 0.3838 0.057 Uiso 1 1 calc R . . H10B H 0.8029 0.5165 0.4251 0.057 Uiso 1 1 calc R . . H10C H 0.8098 0.5885 0.5327 0.057 Uiso 1 1 calc R . . C11 C 0.9532(2) 0.56396(8) 0.9476(2) 0.0260(3) Uani 1 1 d . . . H11A H 1.0489 0.5308 0.9206 0.031 Uiso 1 1 calc R . . C12 C 1.0041(2) 0.62235(8) 1.06484(19) 0.0245(3) Uani 1 1 d . . . C13 C 0.8639(2) 0.66899(9) 1.1209(2) 0.0271(3) Uani 1 1 d . . . C14 C 0.9173(3) 0.72312(9) 1.2369(2) 0.0323(4) Uani 1 1 d . . . H14A H 0.8228 0.7543 1.2765 0.039 Uiso 1 1 calc R . . C15 C 1.1075(3) 0.73106(9) 1.2937(2) 0.0333(4) Uani 1 1 d . . . H15A H 1.1431 0.7686 1.3706 0.040 Uiso 1 1 calc R . . C16 C 1.2483(2) 0.68543(10) 1.2409(2) 0.0330(4) Uani 1 1 d . . . H16A H 1.3786 0.6914 1.2820 0.040 Uiso 1 1 calc R . . C17 C 1.1965(2) 0.63126(9) 1.1279(2) 0.0298(4) Uani 1 1 d . . . H17A H 1.2919 0.5996 1.0923 0.036 Uiso 1 1 calc R . . C18 C 0.8899(2) 0.44806(9) 0.7228(2) 0.0335(4) Uani 1 1 d . . . H18A H 0.9485 0.4239 0.8254 0.050 Uiso 1 1 calc R . . H18B H 0.9868 0.4773 0.6703 0.050 Uiso 1 1 calc R . . H18C H 0.8403 0.4133 0.6372 0.050 Uiso 1 1 calc R . . C19 C 0.4482(3) 0.57276(9) 0.6719(2) 0.0317(4) Uani 1 1 d . . . C20 C 0.3600(3) 0.69039(10) 0.7062(2) 0.0362(4) Uani 1 1 d . . . H20A H 0.3930 0.7368 0.6614 0.054 Uiso 1 1 calc R . . H20B H 0.3643 0.6917 0.8341 0.054 Uiso 1 1 calc R . . H20C H 0.2303 0.6774 0.6609 0.054 Uiso 1 1 calc R . . C21 C 0.5945(2) 0.45359(9) 0.8996(2) 0.0316(4) Uani 1 1 d . . . C22 C 0.4659(2) 0.34344(10) 0.9666(2) 0.0335(4) Uani 1 1 d . . . H22A H 0.4701 0.2945 0.9281 0.050 Uiso 1 1 calc R . . H22B H 0.3333 0.3606 0.9541 0.050 Uiso 1 1 calc R . . H22C H 0.5130 0.3466 1.0894 0.050 Uiso 1 1 calc R . . H1O H 0.506(5) 0.360(2) 0.547(4) 0.100(12) Uiso 1 1 d . . . H2O H 0.670(3) 0.6265(13) 1.000(3) 0.050(6) 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 O1 0.0465(7) 0.0234(6) 0.0430(7) 0.0000(5) -0.0174(5) -0.0007(5) O2 0.0287(6) 0.0385(7) 0.0433(7) -0.0150(6) -0.0033(5) 0.0054(5) O3 0.0743(11) 0.0415(8) 0.1280(15) -0.0387(9) 0.0760(11) -0.0282(8) O4 0.0304(6) 0.0222(6) 0.0404(6) 0.0048(5) 0.0058(5) 0.0032(5) O5 0.1472(18) 0.0373(9) 0.0967(14) -0.0248(8) 0.0977(14) -0.0311(10) O6 0.0293(5) 0.0219(5) 0.0276(5) 0.0009(4) 0.0038(4) -0.0040(4) N1 0.0378(7) 0.0213(7) 0.0216(6) -0.0020(5) 0.0058(5) -0.0035(6) N2 0.0296(7) 0.0215(6) 0.0272(6) -0.0034(5) 0.0049(5) -0.0041(5) C1 0.0380(9) 0.0221(8) 0.0272(8) -0.0028(6) 0.0105(7) -0.0078(6) C2 0.0306(8) 0.0221(8) 0.0304(8) -0.0064(6) 0.0098(7) -0.0058(6) C3 0.0371(9) 0.0219(8) 0.0289(8) 0.0019(6) 0.0072(6) 0.0023(6) C4 0.0295(8) 0.0254(8) 0.0218(7) -0.0009(6) 0.0036(6) -0.0002(6) C5 0.0309(8) 0.0273(8) 0.0238(7) 0.0001(6) 0.0010(6) -0.0013(7) C6 0.0402(9) 0.0282(9) 0.0323(8) -0.0026(7) 0.0029(7) -0.0078(7) C7 0.0333(9) 0.0458(10) 0.0303(9) -0.0046(8) 0.0036(7) -0.0139(8) C8 0.0303(9) 0.0586(13) 0.0388(9) 0.0041(9) -0.0048(7) -0.0049(8) C9 0.0337(8) 0.0387(10) 0.0374(9) 0.0052(8) -0.0010(7) 0.0050(8) C10 0.0490(10) 0.0296(9) 0.0369(9) -0.0025(7) 0.0205(7) -0.0076(8) C11 0.0280(8) 0.0235(8) 0.0273(7) 0.0001(6) 0.0075(6) -0.0013(6) C12 0.0282(8) 0.0212(8) 0.0247(7) 0.0015(6) 0.0054(6) -0.0028(6) C13 0.0277(8) 0.0267(8) 0.0267(7) 0.0018(6) -0.0001(6) 0.0026(6) C14 0.0372(9) 0.0293(9) 0.0297(8) -0.0040(7) -0.0034(7) 0.0060(7) C15 0.0423(9) 0.0283(9) 0.0285(8) -0.0020(7) -0.0036(7) -0.0033(7) C16 0.0305(8) 0.0386(10) 0.0294(8) 0.0010(7) -0.0015(6) -0.0058(7) C17 0.0265(8) 0.0336(9) 0.0297(8) 0.0015(7) 0.0055(6) -0.0009(7) C18 0.0332(9) 0.0280(8) 0.0408(9) -0.0107(7) 0.0146(7) -0.0066(7) C19 0.0392(9) 0.0274(9) 0.0296(8) -0.0082(7) 0.0101(7) -0.0104(7) C20 0.0391(9) 0.0318(9) 0.0379(9) 0.0016(7) 0.0038(7) 0.0114(8) C21 0.0385(9) 0.0252(8) 0.0323(8) -0.0048(7) 0.0117(7) -0.0048(7) C22 0.0352(9) 0.0291(8) 0.0369(9) 0.0050(7) 0.0080(7) -0.0085(7) _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 C5 1.354(2) . ? O1 H1O 0.86(4) . ? O2 C13 1.349(2) . ? O2 H2O 0.86(3) . ? O3 C19 1.184(2) . ? O4 C19 1.318(2) . ? O4 C20 1.453(2) . ? O5 C21 1.186(2) . ? O6 C21 1.327(2) . ? O6 C22 1.4450(19) . ? N1 C3 1.278(2) . ? N1 C1 1.470(2) . ? N2 C11 1.280(2) . ? N2 C2 1.467(2) . ? C1 C10 1.533(2) . ? C1 C19 1.542(2) . ? C1 C2 1.579(2) . ? C2 C18 1.532(2) . ? C2 C21 1.549(2) . ? C3 C4 1.453(2) . ? C3 H3A 0.9500 . ? C4 C9 1.399(2) . ? C4 C5 1.401(2) . ? C5 C6 1.398(2) . ? C6 C7 1.375(3) . ? C6 H6A 0.9500 . ? C7 C8 1.384(3) . ? C7 H7A 0.9500 . ? C8 C9 1.379(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.461(2) . ? C11 H11A 0.9500 . ? C12 C13 1.407(2) . ? C12 C17 1.408(2) . ? C13 C14 1.398(2) . ? C14 C15 1.379(2) . ? C14 H14A 0.9500 . ? C15 C16 1.389(3) . ? C15 H15A 0.9500 . ? C16 C17 1.382(2) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C5 O1 H1O 109(2) . . ? C13 O2 H2O 106.0(15) . . ? C19 O4 C20 115.38(13) . . ? C21 O6 C22 115.92(12) . . ? C3 N1 C1 119.96(14) . . ? C11 N2 C2 121.19(14) . . ? N1 C1 C10 109.79(13) . . ? N1 C1 C19 108.96(13) . . ? C10 C1 C19 111.52(14) . . ? N1 C1 C2 106.61(12) . . ? C10 C1 C2 111.38(14) . . ? C19 C1 C2 108.43(12) . . ? N2 C2 C18 115.59(13) . . ? N2 C2 C21 103.43(12) . . ? C18 C2 C21 110.69(13) . . ? N2 C2 C1 107.43(12) . . ? C18 C2 C1 110.23(13) . . ? C21 C2 C1 109.13(13) . . ? N1 C3 C4 122.07(14) . . ? N1 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C9 C4 C5 118.44(15) . . ? C9 C4 C3 119.79(15) . . ? C5 C4 C3 121.76(14) . . ? O1 C5 C6 118.04(15) . . ? O1 C5 C4 121.78(14) . . ? C6 C5 C4 120.18(14) . . ? C7 C6 C5 119.70(17) . . ? C7 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C6 C7 C8 120.97(17) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 119.50(16) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 C4 121.14(17) . . ? C8 C9 H9A 119.4 . . ? C4 C9 H9A 119.4 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 120.94(14) . . ? N2 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C17 118.91(14) . . ? C13 C12 C11 121.44(14) . . ? C17 C12 C11 119.63(14) . . ? O2 C13 C14 118.44(14) . . ? O2 C13 C12 121.74(14) . . ? C14 C13 C12 119.82(14) . . ? C15 C14 C13 119.74(15) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C14 C15 C16 121.45(16) . . ? C14 C15 H15A 119.3 . . ? C16 C15 H15A 119.3 . . ? C17 C16 C15 119.20(16) . . ? C17 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C16 C17 C12 120.88(16) . . ? C16 C17 H17A 119.6 . . ? C12 C17 H17A 119.6 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 O4 123.32(17) . . ? O3 C19 C1 123.42(16) . . ? O4 C19 C1 113.26(13) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 C21 O6 122.90(16) . . ? O5 C21 C2 125.02(15) . . ? O6 C21 C2 112.00(13) . . ? O6 C22 H22A 109.5 . . ? O6 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O6 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C3 N1 C1 C10 -78.11(19) . . . . ? C3 N1 C1 C19 44.29(18) . . . . ? C3 N1 C1 C2 161.11(13) . . . . ? C11 N2 C2 C18 -13.0(2) . . . . ? C11 N2 C2 C21 108.15(16) . . . . ? C11 N2 C2 C1 -136.51(14) . . . . ? N1 C1 C2 N2 -164.66(12) . . . . ? C10 C1 C2 N2 75.59(16) . . . . ? C19 C1 C2 N2 -47.48(15) . . . . ? N1 C1 C2 C18 68.61(15) . . . . ? C10 C1 C2 C18 -51.14(17) . . . . ? C19 C1 C2 C18 -174.22(12) . . . . ? N1 C1 C2 C21 -53.15(15) . . . . ? C10 C1 C2 C21 -172.90(13) . . . . ? C19 C1 C2 C21 64.03(15) . . . . ? C1 N1 C3 C4 -177.38(13) . . . . ? N1 C3 C4 C9 -179.96(15) . . . . ? N1 C3 C4 C5 1.1(2) . . . . ? C9 C4 C5 O1 -177.71(14) . . . . ? C3 C4 C5 O1 1.2(2) . . . . ? C9 C4 C5 C6 2.5(2) . . . . ? C3 C4 C5 C6 -178.57(15) . . . . ? O1 C5 C6 C7 179.45(16) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C5 C6 C7 C8 -1.7(3) . . . . ? C6 C7 C8 C9 2.2(3) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C5 C4 C9 C8 -1.9(2) . . . . ? C3 C4 C9 C8 179.12(16) . . . . ? C2 N2 C11 C12 -173.55(13) . . . . ? N2 C11 C12 C13 5.8(2) . . . . ? N2 C11 C12 C17 -176.20(14) . . . . ? C17 C12 C13 O2 -179.66(15) . . . . ? C11 C12 C13 O2 -1.6(2) . . . . ? C17 C12 C13 C14 0.2(2) . . . . ? C11 C12 C13 C14 178.23(15) . . . . ? O2 C13 C14 C15 -179.21(15) . . . . ? C12 C13 C14 C15 1.0(2) . . . . ? C13 C14 C15 C16 -1.3(3) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C15 C16 C17 C12 0.6(2) . . . . ? C13 C12 C17 C16 -1.0(2) . . . . ? C11 C12 C17 C16 -179.07(14) . . . . ? C20 O4 C19 O3 0.4(3) . . . . ? C20 O4 C19 C1 -179.43(14) . . . . ? N1 C1 C19 O3 35.3(2) . . . . ? C10 C1 C19 O3 156.6(2) . . . . ? C2 C1 C19 O3 -80.4(2) . . . . ? N1 C1 C19 O4 -144.94(13) . . . . ? C10 C1 C19 O4 -23.6(2) . . . . ? C2 C1 C19 O4 99.40(15) . . . . ? C22 O6 C21 O5 3.8(3) . . . . ? C22 O6 C21 C2 -179.33(13) . . . . ? N2 C2 C21 O5 20.0(3) . . . . ? C18 C2 C21 O5 144.4(2) . . . . ? C1 C2 C21 O5 -94.2(3) . . . . ? N2 C2 C21 O6 -156.76(13) . . . . ? C18 C2 C21 O6 -32.37(19) . . . . ? C1 C2 C21 O6 89.11(16) . . . . ? 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 H1O N1 0.86(4) 1.87(4) 2.6232(17) 146(3) . O1 H1O O6 0.86(4) 2.48(3) 2.9914(17) 119(3) . O2 H2O N2 0.86(3) 1.82(3) 2.6006(18) 151(2) . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 66.31 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.175 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.045 _iucr_refine_instructions_details ; TITL cu_d12336_0m in P2(1) CELL 1.54178 6.9679 19.0540 7.6683 90.000 93.428 90.000 ZERR 2.00 0.0003 0.0009 0.0004 0.000 0.002 0.000 LATT -1 SYMM -x, y+1/2, -z SFAC C H N O UNIT 44 48 4 12 TEMP -126.130 SIZE 0.120 0.150 0.280 ACTA L.S. 4 FMAP 2 PLAN 20 HTAB O1 N1 HTAB O1 O6 HTAB O2 N2 BOND $H CONF WGHT 0.040200 0.212300 FVAR 0.36803 O1 4 0.445574 0.322065 0.520254 11.00000 0.04654 0.02341 = 0.04298 0.00005 -0.01740 -0.00068 O2 4 0.677081 0.663007 1.065905 11.00000 0.02870 0.03854 = 0.04328 -0.01499 -0.00329 0.00545 O3 4 0.303012 0.555429 0.732163 11.00000 0.07428 0.04148 = 0.12797 -0.03874 0.07595 -0.02820 O4 4 0.497040 0.638871 0.649979 11.00000 0.03045 0.02220 = 0.04040 0.00478 0.00585 0.00316 O5 4 0.517307 0.478281 1.018916 11.00000 0.14717 0.03730 = 0.09672 -0.02479 0.09775 -0.03108 O6 4 0.586067 0.385733 0.860927 11.00000 0.02927 0.02185 = 0.02765 0.00092 0.00379 -0.00405 N1 3 0.500264 0.458162 0.537348 11.00000 0.03783 0.02134 = 0.02159 -0.00195 0.00578 -0.00346 N2 3 0.781586 0.556786 0.880888 11.00000 0.02958 0.02154 = 0.02725 -0.00341 0.00485 -0.00405 C1 1 0.599380 0.520349 0.611905 11.00000 0.03797 0.02206 = 0.02724 -0.00283 0.01047 -0.00780 C2 1 0.724594 0.494455 0.777986 11.00000 0.03060 0.02214 = 0.03041 -0.00637 0.00975 -0.00581 C3 1 0.352040 0.465530 0.432540 11.00000 0.03711 0.02188 = 0.02895 0.00190 0.00720 0.00225 AFIX 43 H3A 2 0.311003 0.511528 0.400327 11.00000 -1.20000 AFIX 0 C4 1 0.244300 0.405769 0.361092 11.00000 0.02947 0.02540 = 0.02180 -0.00092 0.00364 -0.00022 C5 1 0.295359 0.336658 0.405786 11.00000 0.03094 0.02730 = 0.02380 0.00014 0.00099 -0.00128 C6 1 0.190916 0.280374 0.331433 11.00000 0.04024 0.02817 = 0.03234 -0.00263 0.00294 -0.00780 AFIX 43 H6A 2 0.226530 0.233515 0.360703 11.00000 -1.20000 AFIX 0 C7 1 0.036435 0.293157 0.215766 11.00000 0.03328 0.04582 = 0.03025 -0.00465 0.00357 -0.01386 AFIX 43 H7A 2 -0.032165 0.254808 0.163088 11.00000 -1.20000 AFIX 0 C8 1 -0.020584 0.361056 0.174957 11.00000 0.03030 0.05865 = 0.03880 0.00414 -0.00478 -0.00488 AFIX 43 H8A 2 -0.130297 0.369265 0.098081 11.00000 -1.20000 AFIX 0 C9 1 0.083079 0.416728 0.246743 11.00000 0.03374 0.03875 = 0.03743 0.00518 -0.00104 0.00496 AFIX 43 H9A 2 0.044315 0.463321 0.218028 11.00000 -1.20000 AFIX 0 C10 1 0.725035 0.553136 0.476141 11.00000 0.04902 0.02959 = 0.03692 -0.00247 0.02052 -0.00765 AFIX 137 H10A 2 0.642752 0.575351 0.383833 11.00000 -1.50000 H10B 2 0.802928 0.516500 0.425114 11.00000 -1.50000 H10C 2 0.809757 0.588519 0.532681 11.00000 -1.50000 AFIX 0 C11 1 0.953227 0.563959 0.947638 11.00000 0.02803 0.02347 = 0.02732 0.00008 0.00749 -0.00134 AFIX 43 H11A 2 1.048900 0.530830 0.920574 11.00000 -1.20000 AFIX 0 C12 1 1.004127 0.622355 1.064837 11.00000 0.02820 0.02119 = 0.02469 0.00148 0.00536 -0.00277 C13 1 0.863895 0.668990 1.120880 11.00000 0.02768 0.02674 = 0.02669 0.00181 -0.00014 0.00265 C14 1 0.917268 0.723123 1.236945 11.00000 0.03721 0.02927 = 0.02969 -0.00402 -0.00343 0.00596 AFIX 43 H14A 2 0.822808 0.754313 1.276542 11.00000 -1.20000 AFIX 0 C15 1 1.107520 0.731061 1.293701 11.00000 0.04230 0.02827 = 0.02853 -0.00197 -0.00365 -0.00326 AFIX 43 H15A 2 1.143127 0.768561 1.370619 11.00000 -1.20000 AFIX 0 C16 1 1.248287 0.685432 1.240887 11.00000 0.03052 0.03860 = 0.02944 0.00101 -0.00152 -0.00583 AFIX 43 H16A 2 1.378609 0.691399 1.281959 11.00000 -1.20000 AFIX 0 C17 1 1.196463 0.631258 1.127886 11.00000 0.02654 0.03364 = 0.02971 0.00145 0.00547 -0.00090 AFIX 43 H17A 2 1.291918 0.599601 1.092278 11.00000 -1.20000 AFIX 0 C18 1 0.889920 0.448062 0.722766 11.00000 0.03321 0.02798 = 0.04078 -0.01075 0.01461 -0.00658 AFIX 137 H18A 2 0.948464 0.423858 0.825424 11.00000 -1.50000 H18B 2 0.986809 0.477301 0.670315 11.00000 -1.50000 H18C 2 0.840266 0.413345 0.637227 11.00000 -1.50000 AFIX 0 C19 1 0.448231 0.572762 0.671909 11.00000 0.03916 0.02741 = 0.02958 -0.00819 0.01009 -0.01037 C20 1 0.359989 0.690389 0.706164 11.00000 0.03905 0.03177 = 0.03787 0.00161 0.00379 0.01139 AFIX 137 H20A 2 0.392951 0.736755 0.661419 11.00000 -1.50000 H20B 2 0.364252 0.691726 0.834093 11.00000 -1.50000 H20C 2 0.230310 0.677440 0.660883 11.00000 -1.50000 AFIX 0 C21 1 0.594473 0.453588 0.899631 11.00000 0.03850 0.02518 = 0.03225 -0.00478 0.01171 -0.00481 C22 1 0.465944 0.343445 0.966626 11.00000 0.03518 0.02907 = 0.03694 0.00505 0.00801 -0.00849 AFIX 137 H22A 2 0.470145 0.294456 0.928111 11.00000 -1.50000 H22B 2 0.333263 0.360615 0.954051 11.00000 -1.50000 H22C 2 0.512955 0.346582 1.089404 11.00000 -1.50000 AFIX 0 H1O 2 0.505775 0.360028 0.547349 11.00000 0.09952 H2O 2 0.669626 0.626540 1.000157 11.00000 0.04979 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_d12336_0m in P2(1) REM R1 = 0.0305 for 3391 Fo > 4sig(Fo) and 0.0306 for all 3412 data REM 283 parameters refined using 1 restraints END WGHT 0.0403 0.2106 REM Highest difference peak 0.175, deepest hole -0.217, 1-sigma level 0.045 Q1 1 0.4533 0.4760 0.9437 11.00000 0.05 0.18 Q2 1 0.3279 0.5449 0.7613 11.00000 0.05 0.14 Q3 1 0.5851 0.4631 1.0359 11.00000 0.05 0.14 Q4 1 0.2614 0.5678 0.6433 11.00000 0.05 0.13 Q5 1 0.2490 0.4202 0.7401 11.00000 0.05 0.12 Q6 1 0.5457 0.3868 1.2550 11.00000 0.05 0.12 Q7 1 0.9949 0.3770 0.5211 11.00000 0.05 0.11 Q8 1 0.7839 0.4297 0.4138 11.00000 0.05 0.11 Q9 1 0.6377 0.3312 1.2607 11.00000 0.05 0.11 Q10 1 0.7217 0.7217 1.3888 11.00000 0.05 0.10 Q11 1 0.7449 0.4486 0.4034 11.00000 0.05 0.10 Q12 1 0.6533 0.7292 0.9001 11.00000 0.05 0.10 Q13 1 0.8119 0.3640 0.4237 11.00000 0.05 0.10 Q14 1 0.2535 0.6689 0.8291 11.00000 0.05 0.10 Q15 1 0.6705 0.4117 1.3080 11.00000 0.05 0.10 Q16 1 0.1224 0.1626 0.3041 11.00000 0.05 0.10 Q17 1 0.5300 0.5974 0.2617 11.00000 0.05 0.09 Q18 1 0.7186 0.6468 0.3999 11.00000 0.05 0.09 Q19 1 0.7472 0.5098 0.3643 11.00000 0.05 0.09 Q20 1 0.1797 0.1844 0.4172 11.00000 0.05 0.09 ; _database_code_depnum_ccdc_archive 'CCDC 953697'