# 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_global data_i _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3R/S,5R/S)-methyl 3-acetamido-5-(dimethylcarbamoyl)-6-methyl-2-(phenylcarbamoyl)- 2,3,4,5-tetrahydropyridazine-3-carboxylate ; _chemical_formula_moiety 'C19 H25 N5 O5' _chemical_formula_sum 'C19 H25 N5 O5' _chemical_formula_weight 403.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9471(4) _cell_length_b 9.6297(3) _cell_length_c 18.1609(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.810(3) _cell_angle_gamma 90.00 _cell_volume 2084.74(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2900 _cell_measurement_theta_min 2.3903 _cell_measurement_theta_max 29.1248 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_min 0.99595 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0827 _diffrn_reflns_number 9580 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 29.19 _reflns_number_total 4739 _reflns_number_gt 2399 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0463P)^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 4739 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 0.813 _refine_ls_restrained_S_all 0.813 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.04280(11) 0.23282(12) 0.63314(7) 0.0341(3) Uani 1 1 d . . . N2 N 0.04207(11) 0.32825(13) 0.69045(7) 0.0371(3) Uani 1 1 d . . . C3 C 0.13347(14) 0.35972(16) 0.72731(9) 0.0388(4) Uani 1 1 d . . . C4 C 0.24532(13) 0.29766(16) 0.71403(9) 0.0398(4) Uani 1 1 d . . . H4 H 0.2576 0.2155 0.7454 0.048 Uiso 1 1 calc R . . C5 C 0.24876(13) 0.25534(17) 0.63375(9) 0.0437(4) Uani 1 1 d . . . H5A H 0.3123 0.1938 0.6295 0.052 Uiso 1 1 calc R . . H5B H 0.2624 0.3379 0.6051 0.052 Uiso 1 1 calc R . . C6 C 0.14312(13) 0.18261(14) 0.59873(9) 0.0337(4) Uani 1 1 d . . . C7 C -0.06051(13) 0.20763(15) 0.59556(9) 0.0325(4) Uani 1 1 d . . . O1 O -0.06463(9) 0.13915(11) 0.53847(6) 0.0415(3) Uani 1 1 d . . . N3 N -0.15003(11) 0.26351(13) 0.62728(8) 0.0353(3) Uani 1 1 d . . . H3 H -0.1342(13) 0.3180(16) 0.6663(9) 0.046(5) Uiso 1 1 d . . . C1' C -0.26266(13) 0.26168(15) 0.59772(9) 0.0360(4) Uani 1 1 d . . . C2' C -0.33431(15) 0.36151(18) 0.62193(10) 0.0514(5) Uani 1 1 d . . . H2' H -0.3085 0.4245 0.6580 0.062 Uiso 1 1 calc R . . C3' C -0.44406(16) 0.3688(2) 0.59308(12) 0.0649(6) Uani 1 1 d . . . H3' H -0.4914 0.4372 0.6094 0.078 Uiso 1 1 calc R . . C4' C -0.48346(16) 0.2759(2) 0.54054(11) 0.0686(6) Uani 1 1 d . . . H4' H -0.5566 0.2826 0.5199 0.082 Uiso 1 1 calc R . . C5' C -0.41386(17) 0.1728(2) 0.51878(11) 0.0650(6) Uani 1 1 d . . . H5' H -0.4412 0.1079 0.4842 0.078 Uiso 1 1 calc R . . C6' C -0.30372(15) 0.16312(18) 0.54714(10) 0.0513(5) Uani 1 1 d . . . H6' H -0.2579 0.0916 0.5325 0.062 Uiso 1 1 calc R . . C8 C 0.12438(16) 0.4619(2) 0.78851(10) 0.0642(6) Uani 1 1 d . . . H8A H 0.0484 0.4942 0.7888 0.096 Uiso 1 1 calc R . . H8B H 0.1732 0.5392 0.7812 0.096 Uiso 1 1 calc R . . H8C H 0.1457 0.4181 0.8348 0.096 Uiso 1 1 calc R . . C9 C 0.33927(14) 0.4022(2) 0.73188(11) 0.0461(5) Uani 1 1 d . . . O2 O 0.34512(11) 0.50540(13) 0.69290(8) 0.0679(4) Uani 1 1 d . . . N4 N 0.41290(13) 0.37864(17) 0.78919(9) 0.0603(5) Uani 1 1 d . . . C10 C 0.50099(19) 0.4825(3) 0.80560(13) 0.0999(9) Uani 1 1 d . . . H10A H 0.5732 0.4392 0.8045 0.150 Uiso 1 1 calc R . . H10B H 0.4928 0.5211 0.8537 0.150 Uiso 1 1 calc R . . H10C H 0.4945 0.5552 0.7694 0.150 Uiso 1 1 calc R . . C11 C 0.4094(2) 0.2641(3) 0.84117(13) 0.1024(9) Uani 1 1 d . . . H11A H 0.3848 0.2976 0.8872 0.154 Uiso 1 1 calc R . . H11B H 0.4829 0.2244 0.8491 0.154 Uiso 1 1 calc R . . H11C H 0.3580 0.1946 0.8215 0.154 Uiso 1 1 calc R . . N5 N 0.14912(12) 0.03183(13) 0.59952(8) 0.0373(4) Uani 1 1 d . . . H5 H 0.1293(15) -0.0050(18) 0.5588(10) 0.062(6) Uiso 1 1 d . . . C12 C 0.16823(14) -0.04863(17) 0.65975(11) 0.0434(4) Uani 1 1 d . . . O3 O 0.18783(11) -0.00202(12) 0.72181(7) 0.0612(4) Uani 1 1 d . . . C13 C 0.16392(18) -0.20275(16) 0.64576(11) 0.0667(6) Uani 1 1 d . . . H13A H 0.2357 -0.2430 0.6598 0.100 Uiso 1 1 calc R . . H13B H 0.1455 -0.2195 0.5943 0.100 Uiso 1 1 calc R . . H13C H 0.1078 -0.2439 0.6743 0.100 Uiso 1 1 calc R . . C14 C 0.14029(14) 0.22627(16) 0.51724(10) 0.0379(4) Uani 1 1 d . . . O4 O 0.18242(11) 0.16039(12) 0.47057(6) 0.0548(4) Uani 1 1 d . . . O5 O 0.09695(10) 0.35249(11) 0.50762(7) 0.0511(3) Uani 1 1 d . . . C15 C 0.1005(2) 0.4103(2) 0.43437(12) 0.0820(7) Uani 1 1 d . . . H15A H 0.1745 0.4449 0.4277 0.123 Uiso 1 1 calc R . . H15B H 0.0474 0.4849 0.4284 0.123 Uiso 1 1 calc R . . H15C H 0.0820 0.3395 0.3984 0.123 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 N1 0.0294(8) 0.0384(7) 0.0346(8) -0.0089(6) 0.0024(6) 0.0018(6) N2 0.0352(9) 0.0424(8) 0.0341(8) -0.0085(7) 0.0052(7) -0.0001(6) C3 0.0372(11) 0.0445(9) 0.0349(10) -0.0058(8) 0.0048(8) -0.0048(8) C4 0.0344(10) 0.0412(9) 0.0432(10) -0.0038(8) -0.0022(8) -0.0001(7) C5 0.0308(10) 0.0522(10) 0.0483(11) -0.0134(9) 0.0045(8) 0.0014(8) C6 0.0301(10) 0.0349(9) 0.0363(10) -0.0026(7) 0.0036(8) 0.0047(7) C7 0.0347(10) 0.0292(8) 0.0332(10) 0.0054(8) 0.0003(8) -0.0002(7) O1 0.0384(7) 0.0478(7) 0.0379(7) -0.0100(6) -0.0005(5) 0.0020(5) N3 0.0293(8) 0.0396(8) 0.0368(8) -0.0043(7) 0.0009(7) 0.0030(6) C1' 0.0310(10) 0.0429(9) 0.0341(9) 0.0030(8) 0.0024(8) 0.0005(8) C2' 0.0373(11) 0.0607(11) 0.0563(12) -0.0116(10) 0.0049(9) 0.0061(9) C3' 0.0386(12) 0.0812(14) 0.0751(15) -0.0109(12) 0.0053(11) 0.0157(10) C4' 0.0322(12) 0.1136(17) 0.0590(14) -0.0040(13) -0.0042(10) 0.0099(12) C5' 0.0446(13) 0.0917(15) 0.0578(14) -0.0203(12) -0.0038(11) -0.0072(11) C6' 0.0380(11) 0.0587(11) 0.0568(12) -0.0113(10) 0.0006(9) 0.0004(9) C8 0.0505(13) 0.0835(13) 0.0593(13) -0.0363(12) 0.0085(10) -0.0037(10) C9 0.0354(11) 0.0545(11) 0.0485(12) -0.0124(10) 0.0042(9) -0.0015(8) O2 0.0679(10) 0.0565(8) 0.0788(10) -0.0002(8) 0.0009(8) -0.0169(7) N4 0.0429(10) 0.0856(12) 0.0510(10) -0.0097(9) -0.0071(8) -0.0154(8) C10 0.0688(17) 0.147(2) 0.0824(18) -0.0239(16) -0.0084(14) -0.0499(16) C11 0.096(2) 0.125(2) 0.0797(18) 0.0145(17) -0.0434(16) -0.0160(16) N5 0.0454(10) 0.0333(8) 0.0329(9) -0.0011(7) 0.0000(7) 0.0081(6) C12 0.0374(11) 0.0456(10) 0.0468(12) 0.0061(10) -0.0001(9) 0.0043(8) O3 0.0818(11) 0.0584(8) 0.0412(8) 0.0058(7) -0.0124(7) -0.0060(7) C13 0.0904(17) 0.0416(11) 0.0666(15) 0.0102(10) -0.0058(12) 0.0083(10) C14 0.0362(10) 0.0338(9) 0.0441(11) -0.0015(8) 0.0056(8) -0.0014(8) O4 0.0740(10) 0.0505(7) 0.0417(8) -0.0020(6) 0.0183(7) 0.0106(7) O5 0.0605(9) 0.0360(6) 0.0582(9) 0.0113(6) 0.0143(7) 0.0093(6) C15 0.101(2) 0.0662(13) 0.0820(17) 0.0428(12) 0.0266(14) 0.0109(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 N2 1.3889(16) . ? N1 C7 1.3915(19) . ? N1 C6 1.4697(19) . ? N2 C3 1.2787(19) . ? C3 C8 1.494(2) . ? C3 C4 1.498(2) . ? C4 C5 1.517(2) . ? C4 C9 1.526(2) . ? C4 H4 0.9800 . ? C5 C6 1.543(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N5 1.4537(18) . ? C6 C14 1.537(2) . ? C7 O1 1.2270(17) . ? C7 N3 1.359(2) . ? N3 C1' 1.415(2) . ? N3 H3 0.891(16) . ? C1' C2' 1.378(2) . ? C1' C6' 1.388(2) . ? C2' C3' 1.381(2) . ? C2' H2' 0.9300 . ? C3' C4' 1.369(3) . ? C3' H3' 0.9300 . ? C4' C5' 1.370(3) . ? C4' H4' 0.9300 . ? C5' C6' 1.384(2) . ? C5' H5' 0.9300 . ? C6' H6' 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O2 1.225(2) . ? C9 N4 1.337(2) . ? N4 C11 1.455(3) . ? N4 C10 1.468(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N5 C12 1.347(2) . ? N5 H5 0.840(17) . ? C12 O3 1.2213(19) . ? C12 C13 1.506(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O4 1.1962(18) . ? C14 O5 1.3281(18) . ? O5 C15 1.445(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 N2 N1 C7 115.68(13) . . ? N2 N1 C6 125.61(12) . . ? C7 N1 C6 117.12(12) . . ? C3 N2 N1 120.09(14) . . ? N2 C3 C8 116.35(15) . . ? N2 C3 C4 124.13(14) . . ? C8 C3 C4 119.50(14) . . ? C3 C4 C5 110.08(13) . . ? C3 C4 C9 110.73(13) . . ? C5 C4 C9 108.35(14) . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? C9 C4 H4 109.2 . . ? C4 C5 C6 116.38(14) . . ? C4 C5 H5A 108.2 . . ? C6 C5 H5A 108.2 . . ? C4 C5 H5B 108.2 . . ? C6 C5 H5B 108.2 . . ? H5A C5 H5B 107.3 . . ? N5 C6 N1 111.44(13) . . ? N5 C6 C14 106.30(12) . . ? N1 C6 C14 110.67(12) . . ? N5 C6 C5 114.26(13) . . ? N1 C6 C5 110.07(12) . . ? C14 C6 C5 103.75(13) . . ? O1 C7 N3 125.62(15) . . ? O1 C7 N1 119.51(15) . . ? N3 C7 N1 114.86(14) . . ? C7 N3 C1' 126.11(14) . . ? C7 N3 H3 116.0(11) . . ? C1' N3 H3 117.0(11) . . ? C2' C1' C6' 119.24(16) . . ? C2' C1' N3 117.73(14) . . ? C6' C1' N3 123.02(15) . . ? C1' C2' C3' 120.57(17) . . ? C1' C2' H2' 119.7 . . ? C3' C2' H2' 119.7 . . ? C4' C3' C2' 120.33(18) . . ? C4' C3' H3' 119.8 . . ? C2' C3' H3' 119.8 . . ? C3' C4' C5' 119.18(18) . . ? C3' C4' H4' 120.4 . . ? C5' C4' H4' 120.4 . . ? C4' C5' C6' 121.46(18) . . ? C4' C5' H5' 119.3 . . ? C6' C5' H5' 119.3 . . ? C5' C6' C1' 119.06(17) . . ? C5' C6' H6' 120.5 . . ? C1' C6' H6' 120.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 N4 121.85(17) . . ? O2 C9 C4 118.80(16) . . ? N4 C9 C4 119.35(17) . . ? C9 N4 C11 126.01(16) . . ? C9 N4 C10 117.92(18) . . ? C11 N4 C10 115.88(17) . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 N5 C6 126.01(15) . . ? C12 N5 H5 119.7(12) . . ? C6 N5 H5 113.7(12) . . ? O3 C12 N5 123.34(15) . . ? O3 C12 C13 121.34(16) . . ? N5 C12 C13 115.32(16) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 O5 124.81(16) . . ? O4 C14 C6 123.63(14) . . ? O5 C14 C6 111.14(14) . . ? C14 O5 C15 116.01(14) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C7 N1 N2 C3 -178.82(14) . . . . ? C6 N1 N2 C3 -13.7(2) . . . . ? N1 N2 C3 C8 -179.27(13) . . . . ? N1 N2 C3 C4 -1.2(2) . . . . ? N2 C3 C4 C5 28.6(2) . . . . ? C8 C3 C4 C5 -153.39(15) . . . . ? N2 C3 C4 C9 148.37(17) . . . . ? C8 C3 C4 C9 -33.6(2) . . . . ? C3 C4 C5 C6 -42.63(19) . . . . ? C9 C4 C5 C6 -163.85(13) . . . . ? N2 N1 C6 N5 125.86(14) . . . . ? C7 N1 C6 N5 -69.19(16) . . . . ? N2 N1 C6 C14 -116.07(15) . . . . ? C7 N1 C6 C14 48.88(17) . . . . ? N2 N1 C6 C5 -1.97(19) . . . . ? C7 N1 C6 C5 162.98(13) . . . . ? C4 C5 C6 N5 -95.68(17) . . . . ? C4 C5 C6 N1 30.58(18) . . . . ? C4 C5 C6 C14 149.03(14) . . . . ? N2 N1 C7 O1 170.47(12) . . . . ? C6 N1 C7 O1 4.0(2) . . . . ? N2 N1 C7 N3 -9.65(19) . . . . ? C6 N1 C7 N3 -176.11(12) . . . . ? O1 C7 N3 C1' -4.9(2) . . . . ? N1 C7 N3 C1' 175.21(13) . . . . ? C7 N3 C1' C2' -157.34(15) . . . . ? C7 N3 C1' C6' 23.9(2) . . . . ? C6' C1' C2' C3' -3.8(3) . . . . ? N3 C1' C2' C3' 177.41(17) . . . . ? C1' C2' C3' C4' 0.7(3) . . . . ? C2' C3' C4' C5' 2.2(3) . . . . ? C3' C4' C5' C6' -1.9(3) . . . . ? C4' C5' C6' C1' -1.2(3) . . . . ? C2' C1' C6' C5' 4.0(3) . . . . ? N3 C1' C6' C5' -177.27(17) . . . . ? C3 C4 C9 O2 -67.4(2) . . . . ? C5 C4 C9 O2 53.5(2) . . . . ? C3 C4 C9 N4 112.86(18) . . . . ? C5 C4 C9 N4 -126.32(17) . . . . ? O2 C9 N4 C11 176.16(19) . . . . ? C4 C9 N4 C11 -4.1(3) . . . . ? O2 C9 N4 C10 1.3(3) . . . . ? C4 C9 N4 C10 -178.93(17) . . . . ? N1 C6 N5 C12 -68.8(2) . . . . ? C14 C6 N5 C12 170.50(15) . . . . ? C5 C6 N5 C12 56.7(2) . . . . ? C6 N5 C12 O3 -3.3(3) . . . . ? C6 N5 C12 C13 176.75(16) . . . . ? N5 C6 C14 O4 -28.7(2) . . . . ? N1 C6 C14 O4 -149.85(16) . . . . ? C5 C6 C14 O4 92.12(18) . . . . ? N5 C6 C14 O5 158.45(13) . . . . ? N1 C6 C14 O5 37.29(17) . . . . ? C5 C6 C14 O5 -80.74(15) . . . . ? O4 C14 O5 C15 1.2(2) . . . . ? C6 C14 O5 C15 173.94(15) . . . . ? _diffrn_measured_fraction_theta_max 0.841 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.157 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 863777' ####################################################################### # # 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_global data_ii _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3R/S,5S/R)-methyl 3-acetamido-5-(dimethylcarbamoyl)-6-methyl-2-(phenylcarbamoyl)- 2,3,4,5-tetrahydropyridazine-3-carboxylate compound with ethyl acetate ; _chemical_formula_moiety 'C19 H25 N5 O5, C4 H8 O2' _chemical_formula_sum 'C23 H33 N5 O7' _chemical_formula_weight 491.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.0057(7) _cell_length_b 9.0537(3) _cell_length_c 18.9373(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.479(4) _cell_angle_gamma 90.00 _cell_volume 2553.64(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3506 _cell_measurement_theta_min 2.2086 _cell_measurement_theta_max 28.9935 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_min 0.98234 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0827 _diffrn_reflns_number 11404 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 29.06 _reflns_number_total 5813 _reflns_number_gt 2867 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0516P)^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_number_reflns 5813 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0991 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _refine_ls_shift/su_max 0.040 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.45402(9) 0.21048(14) 0.84387(7) 0.0323(3) Uani 1 1 d . . . N2 N 0.44367(10) 0.26691(15) 0.77290(7) 0.0384(4) Uani 1 1 d . . . C3 C 0.36626(12) 0.3154(2) 0.73165(9) 0.0395(4) Uani 1 1 d . . . C4 C 0.28754(10) 0.31199(18) 0.75748(8) 0.0335(4) Uani 1 1 d . . . H4 H 0.2939 0.3933 0.7932 0.040 Uiso 1 1 calc R . . C5 C 0.29108(10) 0.16703(17) 0.79852(8) 0.0333(4) Uani 1 1 d . . . H5A H 0.2810 0.0862 0.7627 0.040 Uiso 1 1 calc R . . H5B H 0.2434 0.1651 0.8186 0.040 Uiso 1 1 calc R . . C6 C 0.38190(11) 0.14484(17) 0.86386(8) 0.0292(4) Uani 1 1 d . . . C7 C 0.53998(11) 0.21027(17) 0.89819(9) 0.0314(4) Uani 1 1 d . . . O1 O 0.55179(8) 0.16650(13) 0.96254(6) 0.0399(3) Uani 1 1 d . . . N3 N 0.60508(10) 0.26504(16) 0.87572(8) 0.0365(4) Uani 1 1 d . . . H3 H 0.5865(12) 0.298(2) 0.8305(10) 0.057(6) Uiso 1 1 d . . . C1' C 0.69628(11) 0.27872(18) 0.92163(9) 0.0334(4) Uani 1 1 d . . . C2' C 0.74589(12) 0.3865(2) 0.90248(9) 0.0432(5) Uani 1 1 d . . . H2' H 0.7178 0.4483 0.8614 0.052 Uiso 1 1 calc R . . C3' C 0.83634(13) 0.4030(2) 0.94375(11) 0.0539(5) Uani 1 1 d . . . H3' H 0.8690 0.4742 0.9295 0.065 Uiso 1 1 calc R . . C4' C 0.87840(14) 0.3156(2) 1.00543(12) 0.0614(6) Uani 1 1 d . . . H4' H 0.9392 0.3277 1.0337 0.074 Uiso 1 1 calc R . . C5' C 0.82917(14) 0.2090(2) 1.02513(11) 0.0607(6) Uani 1 1 d . . . H5' H 0.8572 0.1497 1.0673 0.073 Uiso 1 1 calc R . . C6' C 0.73890(12) 0.1889(2) 0.98307(10) 0.0456(5) Uani 1 1 d . . . H6' H 0.7070 0.1149 0.9962 0.055 Uiso 1 1 calc R . . C8 C 0.35622(14) 0.3752(3) 0.65525(10) 0.0727(7) Uani 1 1 d . . . H8A H 0.4138 0.3770 0.6503 0.109 Uiso 1 1 calc R . . H8B H 0.3324 0.4737 0.6501 0.109 Uiso 1 1 calc R . . H8C H 0.3160 0.3134 0.6164 0.109 Uiso 1 1 calc R . . C9 C 0.19866(12) 0.3286(2) 0.69184(9) 0.0396(4) Uani 1 1 d . . . O2 O 0.16257(9) 0.22024(16) 0.65443(7) 0.0650(4) Uani 1 1 d . . . N4 N 0.16290(10) 0.46402(18) 0.67475(8) 0.0494(4) Uani 1 1 d . . . C10 C 0.07961(14) 0.4821(3) 0.60932(12) 0.0775(7) Uani 1 1 d . . . H10A H 0.0529 0.3871 0.5930 0.116 Uiso 1 1 calc R . . H10B H 0.0923 0.5283 0.5687 0.116 Uiso 1 1 calc R . . H10C H 0.0388 0.5428 0.6232 0.116 Uiso 1 1 calc R . . C11 C 0.20137(16) 0.5981(2) 0.71660(12) 0.0749(7) Uani 1 1 d . . . H11A H 0.2013 0.5912 0.7672 0.112 Uiso 1 1 calc R . . H11B H 0.1662 0.6818 0.6914 0.112 Uiso 1 1 calc R . . H11C H 0.2619 0.6097 0.7188 0.112 Uiso 1 1 calc R . . N5 N 0.39737(9) -0.01128(15) 0.88216(8) 0.0330(4) Uani 1 1 d . . . H5 H 0.4102(10) -0.0369(17) 0.9281(9) 0.034(5) Uiso 1 1 d . . . C12 C 0.40379(11) -0.11351(19) 0.83279(9) 0.0359(4) Uani 1 1 d . . . O3 O 0.39385(8) -0.08409(14) 0.76736(6) 0.0512(4) Uani 1 1 d . . . C13 C 0.42440(14) -0.26709(19) 0.86368(10) 0.0551(6) Uani 1 1 d . . . H13A H 0.3704 -0.3130 0.8638 0.083 Uiso 1 1 calc R . . H13B H 0.4677 -0.2632 0.9146 0.083 Uiso 1 1 calc R . . H13C H 0.4483 -0.3234 0.8325 0.083 Uiso 1 1 calc R . . C14 C 0.37612(11) 0.22065(19) 0.93466(9) 0.0340(4) Uani 1 1 d . . . O4 O 0.35723(9) 0.15733(13) 0.98201(6) 0.0486(3) Uani 1 1 d . . . O5 O 0.38770(8) 0.36652(12) 0.93225(6) 0.0416(3) Uani 1 1 d . . . C15 C 0.37099(14) 0.4528(2) 0.99003(10) 0.0542(5) Uani 1 1 d . . . H15A H 0.3086 0.4791 0.9728 0.081 Uiso 1 1 calc R . . H15B H 0.4068 0.5409 0.9999 0.081 Uiso 1 1 calc R . . H15C H 0.3865 0.3957 1.0358 0.081 Uiso 1 1 calc R . . C16 C 0.13310(16) 0.2402(3) 0.95362(13) 0.0815(7) Uani 1 1 d . A . H16A H 0.1809 0.1750 0.9548 0.122 Uiso 1 1 calc R . . H16B H 0.0815 0.1832 0.9509 0.122 Uiso 1 1 calc R . . H16C H 0.1521 0.2995 0.9988 0.122 Uiso 1 1 calc R . . C17 C 0.11019(19) 0.3357(3) 0.88748(14) 0.0721(7) Uani 1 1 d . . . O7A O 0.0269(4) 0.3915(9) 0.8700(4) 0.0796(17) Uani 0.640(18) 1 d P A 1 C18A C -0.0099(7) 0.5074(8) 0.8093(5) 0.111(3) Uani 0.640(18) 1 d P A 1 H18A H -0.0534 0.5681 0.8205 0.133 Uiso 0.640(18) 1 calc PR A 1 H18B H 0.0384 0.5707 0.8079 0.133 Uiso 0.640(18) 1 calc PR A 1 C19A C -0.0482(11) 0.4417(18) 0.7435(8) 0.171(7) Uani 0.640(18) 1 d P A 1 H19A H -0.1016 0.3922 0.7425 0.256 Uiso 0.640(18) 1 calc PR A 1 H19B H -0.0074 0.3709 0.7362 0.256 Uiso 0.640(18) 1 calc PR A 1 H19C H -0.0635 0.5140 0.7037 0.256 Uiso 0.640(18) 1 calc PR A 1 O7B O 0.0232(9) 0.330(2) 0.8429(10) 0.106(4) Uani 0.360(18) 1 d P A 2 C18B C 0.0104(11) 0.439(4) 0.7842(14) 0.172(11) Uani 0.360(18) 1 d P A 2 H18C H 0.0412 0.4113 0.7507 0.207 Uiso 0.360(18) 1 calc PR A 2 H18D H 0.0320 0.5353 0.8061 0.207 Uiso 0.360(18) 1 calc PR A 2 C19B C -0.0864(14) 0.4413(17) 0.7440(13) 0.099(5) Uani 0.360(18) 1 d P A 2 H19D H -0.1066 0.3442 0.7250 0.148 Uiso 0.360(18) 1 calc PR A 2 H19E H -0.1012 0.5096 0.7024 0.148 Uiso 0.360(18) 1 calc PR A 2 H19F H -0.1153 0.4713 0.7781 0.148 Uiso 0.360(18) 1 calc PR A 2 O6 O 0.16044(13) 0.3792(2) 0.85876(10) 0.1092(7) Uani 1 1 d . A . 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 N1 0.0349(8) 0.0387(9) 0.0236(7) 0.0071(6) 0.0112(6) -0.0005(7) N2 0.0413(9) 0.0484(10) 0.0273(7) 0.0099(7) 0.0148(7) 0.0013(7) C3 0.0410(11) 0.0466(12) 0.0303(9) 0.0097(8) 0.0123(8) 0.0004(9) C4 0.0360(10) 0.0334(10) 0.0300(8) 0.0021(8) 0.0108(8) 0.0024(8) C5 0.0339(10) 0.0362(11) 0.0316(8) 0.0009(8) 0.0140(8) 0.0007(8) C6 0.0379(10) 0.0271(10) 0.0252(8) 0.0025(7) 0.0145(7) 0.0012(8) C7 0.0391(10) 0.0277(10) 0.0288(9) -0.0023(8) 0.0140(8) 0.0006(8) O1 0.0461(8) 0.0478(8) 0.0250(6) 0.0074(5) 0.0121(5) 0.0004(6) N3 0.0362(9) 0.0462(10) 0.0263(8) 0.0050(7) 0.0106(7) -0.0025(7) C1' 0.0360(10) 0.0348(10) 0.0294(9) -0.0046(8) 0.0119(8) 0.0016(8) C2' 0.0456(12) 0.0443(12) 0.0401(10) 0.0018(9) 0.0161(9) -0.0045(9) C3' 0.0515(13) 0.0532(13) 0.0573(12) -0.0058(11) 0.0201(11) -0.0125(11) C4' 0.0411(12) 0.0657(16) 0.0652(14) -0.0070(12) 0.0051(11) -0.0053(11) C5' 0.0503(13) 0.0648(15) 0.0551(12) 0.0130(11) 0.0055(11) 0.0077(11) C6' 0.0422(12) 0.0430(12) 0.0462(10) 0.0047(9) 0.0096(9) 0.0014(9) C8 0.0559(14) 0.117(2) 0.0487(11) 0.0425(13) 0.0231(10) 0.0152(13) C9 0.0421(11) 0.0407(12) 0.0348(10) 0.0036(9) 0.0128(8) 0.0011(9) O2 0.0665(10) 0.0538(10) 0.0527(8) -0.0026(7) -0.0042(7) -0.0049(8) N4 0.0452(10) 0.0493(11) 0.0482(9) 0.0115(8) 0.0109(8) 0.0126(8) C10 0.0546(15) 0.0931(19) 0.0706(15) 0.0256(13) 0.0061(12) 0.0252(13) C11 0.0944(19) 0.0425(14) 0.0797(15) 0.0108(13) 0.0224(14) 0.0172(13) N5 0.0487(10) 0.0285(9) 0.0228(7) 0.0026(7) 0.0143(7) 0.0025(7) C12 0.0390(11) 0.0350(11) 0.0308(9) -0.0053(9) 0.0093(8) 0.0026(8) O3 0.0687(9) 0.0568(9) 0.0275(6) -0.0004(6) 0.0168(6) 0.0190(7) C13 0.0764(16) 0.0342(12) 0.0488(11) -0.0038(9) 0.0161(11) 0.0025(10) C14 0.0395(10) 0.0315(10) 0.0320(9) 0.0015(8) 0.0142(8) 0.0010(8) O4 0.0798(10) 0.0388(8) 0.0419(7) 0.0025(6) 0.0395(7) -0.0001(7) O5 0.0621(9) 0.0294(7) 0.0393(6) -0.0039(6) 0.0257(6) -0.0007(6) C15 0.0800(16) 0.0388(12) 0.0500(11) -0.0137(9) 0.0311(11) 0.0044(10) C16 0.0751(18) 0.0855(19) 0.0774(16) 0.0081(15) 0.0200(13) -0.0026(14) C17 0.0736(19) 0.0721(18) 0.0764(17) -0.0032(14) 0.0343(16) -0.0002(15) O7A 0.057(2) 0.092(4) 0.082(3) 0.021(3) 0.017(2) 0.008(2) C18A 0.087(5) 0.117(5) 0.134(7) -0.030(5) 0.046(5) 0.009(4) C19A 0.140(16) 0.269(14) 0.093(7) 0.033(8) 0.031(8) -0.040(11) O7B 0.092(5) 0.117(10) 0.094(8) 0.025(6) 0.016(5) -0.004(6) C18B 0.106(12) 0.29(3) 0.121(15) 0.123(16) 0.039(9) 0.109(14) C19B 0.080(11) 0.086(8) 0.122(9) 0.040(6) 0.025(7) 0.016(6) O6 0.1050(15) 0.1319(17) 0.1182(14) 0.0245(12) 0.0735(13) 0.0181(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C7 1.384(2) . ? N1 N2 1.3898(16) . ? N1 C6 1.466(2) . ? N2 C3 1.276(2) . ? C3 C8 1.498(2) . ? C3 C4 1.510(2) . ? C4 C9 1.515(2) . ? C4 C5 1.516(2) . ? C4 H4 0.9800 . ? C5 C6 1.539(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N5 1.455(2) . ? C6 C14 1.539(2) . ? C7 O1 1.2284(17) . ? C7 N3 1.355(2) . ? N3 C1' 1.404(2) . ? N3 H3 0.853(17) . ? C1' C6' 1.378(2) . ? C1' C2' 1.388(2) . ? C2' C3' 1.379(2) . ? C2' H2' 0.9300 . ? C3' C4' 1.367(3) . ? C3' H3' 0.9300 . ? C4' C5' 1.381(3) . ? C4' H4' 0.9300 . ? C5' C6' 1.383(3) . ? C5' H5' 0.9300 . ? C6' H6' 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O2 1.224(2) . ? C9 N4 1.342(2) . ? N4 C11 1.457(3) . ? N4 C10 1.459(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N5 C12 1.346(2) . ? N5 H5 0.850(15) . ? C12 O3 1.2194(17) . ? C12 C13 1.498(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O4 1.1927(17) . ? C14 O5 1.3367(19) . ? O5 C15 1.4470(18) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.454(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O6 1.191(3) . ? C17 O7B 1.339(13) . ? C17 O7A 1.348(7) . ? O7A C18A 1.507(10) . ? C18A C19A 1.313(15) . ? C18A H18A 0.9700 . ? C18A H18B 0.9700 . ? C19A H19A 0.9600 . ? C19A H19B 0.9600 . ? C19A H19C 0.9600 . ? O7B C18B 1.447(19) . ? C18B C19B 1.45(3) . ? C18B H18C 0.9700 . ? C18B H18D 0.9700 . ? C19B H19D 0.9600 . ? C19B H19E 0.9600 . ? C19B H19F 0.9600 . ? 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 C7 N1 N2 116.95(13) . . ? C7 N1 C6 118.04(12) . . ? N2 N1 C6 124.92(13) . . ? C3 N2 N1 117.61(14) . . ? N2 C3 C8 116.90(16) . . ? N2 C3 C4 122.21(14) . . ? C8 C3 C4 120.89(15) . . ? C3 C4 C9 112.11(13) . . ? C3 C4 C5 107.74(13) . . ? C9 C4 C5 110.74(14) . . ? C3 C4 H4 108.7 . . ? C9 C4 H4 108.7 . . ? C5 C4 H4 108.7 . . ? C4 C5 C6 111.87(13) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N5 C6 N1 111.96(13) . . ? N5 C6 C5 110.29(13) . . ? N1 C6 C5 109.93(12) . . ? N5 C6 C14 106.56(12) . . ? N1 C6 C14 110.39(12) . . ? C5 C6 C14 107.57(13) . . ? O1 C7 N3 124.94(16) . . ? O1 C7 N1 119.19(15) . . ? N3 C7 N1 115.82(14) . . ? C7 N3 C1' 125.60(14) . . ? C7 N3 H3 114.8(13) . . ? C1' N3 H3 119.5(13) . . ? C6' C1' C2' 118.81(16) . . ? C6' C1' N3 123.48(16) . . ? C2' C1' N3 117.70(15) . . ? C3' C2' C1' 120.72(17) . . ? C3' C2' H2' 119.6 . . ? C1' C2' H2' 119.6 . . ? C4' C3' C2' 120.53(18) . . ? C4' C3' H3' 119.7 . . ? C2' C3' H3' 119.7 . . ? C3' C4' C5' 118.98(19) . . ? C3' C4' H4' 120.5 . . ? C5' C4' H4' 120.5 . . ? C4' C5' C6' 121.03(19) . . ? C4' C5' H5' 119.5 . . ? C6' C5' H5' 119.5 . . ? C1' C6' C5' 119.91(18) . . ? C1' C6' H6' 120.0 . . ? C5' C6' H6' 120.0 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 N4 121.57(17) . . ? O2 C9 C4 119.85(17) . . ? N4 C9 C4 118.55(17) . . ? C9 N4 C11 124.90(16) . . ? C9 N4 C10 118.93(17) . . ? C11 N4 C10 116.17(16) . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 N5 C6 123.52(13) . . ? C12 N5 H5 118.2(11) . . ? C6 N5 H5 117.7(11) . . ? O3 C12 N5 122.74(16) . . ? O3 C12 C13 121.86(15) . . ? N5 C12 C13 115.40(14) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 O5 125.25(14) . . ? O4 C14 C6 123.59(15) . . ? O5 C14 C6 110.95(13) . . ? C14 O5 C15 116.19(12) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O6 C17 O7B 116.4(7) . . ? O6 C17 O7A 122.4(4) . . ? O7B C17 O7A 32.2(7) . . ? O6 C17 C16 126.2(3) . . ? O7B C17 C16 113.3(6) . . ? O7A C17 C16 110.5(3) . . ? C17 O7A C18A 121.6(6) . . ? C19A C18A O7A 108.9(9) . . ? C19A C18A H18A 109.9 . . ? O7A C18A H18A 109.9 . . ? C19A C18A H18B 109.9 . . ? O7A C18A H18B 109.9 . . ? H18A C18A H18B 108.3 . . ? C17 O7B C18B 106.2(13) . . ? O7B C18B C19B 103.6(15) . . ? O7B C18B H18C 111.0 . . ? C19B C18B H18C 111.0 . . ? O7B C18B H18D 111.0 . . ? C19B C18B H18D 111.0 . . ? H18C C18B H18D 109.0 . . ? C18B C19B H19D 109.5 . . ? C18B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C18B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 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 C7 N1 N2 C3 -156.36(15) . . . . ? C6 N1 N2 C3 27.0(2) . . . . ? N1 N2 C3 C8 -179.78(16) . . . . ? N1 N2 C3 C4 -0.3(2) . . . . ? N2 C3 C4 C9 -161.84(17) . . . . ? C8 C3 C4 C9 17.6(2) . . . . ? N2 C3 C4 C5 -39.8(2) . . . . ? C8 C3 C4 C5 139.67(18) . . . . ? C3 C4 C5 C6 55.15(16) . . . . ? C9 C4 C5 C6 178.08(13) . . . . ? C7 N1 C6 N5 -61.51(17) . . . . ? N2 N1 C6 N5 115.13(15) . . . . ? C7 N1 C6 C5 175.54(13) . . . . ? N2 N1 C6 C5 -7.8(2) . . . . ? C7 N1 C6 C14 57.03(18) . . . . ? N2 N1 C6 C14 -126.32(15) . . . . ? C4 C5 C6 N5 -157.71(12) . . . . ? C4 C5 C6 N1 -33.78(17) . . . . ? C4 C5 C6 C14 86.45(15) . . . . ? N2 N1 C7 O1 177.33(13) . . . . ? C6 N1 C7 O1 -5.8(2) . . . . ? N2 N1 C7 N3 -0.3(2) . . . . ? C6 N1 C7 N3 176.63(13) . . . . ? O1 C7 N3 C1' 1.0(3) . . . . ? N1 C7 N3 C1' 178.43(15) . . . . ? C7 N3 C1' C6' 27.4(3) . . . . ? C7 N3 C1' C2' -154.18(16) . . . . ? C6' C1' C2' C3' 0.5(3) . . . . ? N3 C1' C2' C3' -178.06(16) . . . . ? C1' C2' C3' C4' -1.5(3) . . . . ? C2' C3' C4' C5' 0.9(3) . . . . ? C3' C4' C5' C6' 0.7(3) . . . . ? C2' C1' C6' C5' 1.1(3) . . . . ? N3 C1' C6' C5' 179.55(17) . . . . ? C4' C5' C6' C1' -1.7(3) . . . . ? C3 C4 C9 O2 83.9(2) . . . . ? C5 C4 C9 O2 -36.5(2) . . . . ? C3 C4 C9 N4 -93.98(18) . . . . ? C5 C4 C9 N4 145.67(15) . . . . ? O2 C9 N4 C11 179.67(18) . . . . ? C4 C9 N4 C11 -2.5(3) . . . . ? O2 C9 N4 C10 -0.8(3) . . . . ? C4 C9 N4 C10 176.99(16) . . . . ? N1 C6 N5 C12 -61.0(2) . . . . ? C5 C6 N5 C12 61.7(2) . . . . ? C14 C6 N5 C12 178.21(15) . . . . ? C6 N5 C12 O3 -2.8(3) . . . . ? C6 N5 C12 C13 177.07(15) . . . . ? N5 C6 C14 O4 -22.8(2) . . . . ? N1 C6 C14 O4 -144.61(17) . . . . ? C5 C6 C14 O4 95.45(19) . . . . ? N5 C6 C14 O5 162.24(13) . . . . ? N1 C6 C14 O5 40.45(18) . . . . ? C5 C6 C14 O5 -79.49(16) . . . . ? O4 C14 O5 C15 -3.4(2) . . . . ? C6 C14 O5 C15 171.42(14) . . . . ? O6 C17 O7A C18A 3.5(10) . . . . ? O7B C17 O7A C18A -85.5(15) . . . . ? C16 C17 O7A C18A 173.0(5) . . . . ? C17 O7A C18A C19A 87.9(18) . . . . ? O6 C17 O7B C18B -26.1(15) . . . . ? O7A C17 O7B C18B 83.3(19) . . . . ? C16 C17 O7B C18B 175.1(13) . . . . ? C17 O7B C18B C19B -173(3) . . . . ? _diffrn_measured_fraction_theta_max 0.851 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.198 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 863864'