# Electronic Supplementary Material (ESI) for Chemical Communications # 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_ke1110m _audit_creation_method SHELXL-97 _chemical_name_systematic ; KEDP1 3H-imidazo[4,5-b]pyridine, 1,3-diphenylurea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H5 N3) (C13 H12 N2 O) ; _chemical_formula_sum 'C19 H17 N5 O' _chemical_formula_weight 331.38 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 C2/c 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' '-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 24.508(3) _cell_length_b 19.467(3) _cell_length_c 6.9054(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.327(6) _cell_angle_gamma 90.00 _cell_volume 3218.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3576 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 29.82 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13000 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 32.03 _reflns_number_total 4476 _reflns_number_gt 2785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^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 4476 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.06485(8) 0.58627(9) -0.0152(2) 0.0355(4) Uani 1 1 d . . . H11 H 0.0265 0.5965 -0.0652 0.043 Uiso 1 1 calc R . . C12 C 0.08278(7) 0.51814(9) -0.0015(2) 0.0338(4) Uani 1 1 d . . . H12 H 0.0555 0.4836 -0.0436 0.041 Uiso 1 1 calc R . . N13 N 0.13544(6) 0.49776(7) 0.06625(19) 0.0308(3) Uani 1 1 d . . . C14 C 0.17134(7) 0.54918(8) 0.1235(2) 0.0267(4) Uani 1 1 d . . . C15 C 0.15693(7) 0.61897(8) 0.1150(2) 0.0279(4) Uani 1 1 d . . . C16 C 0.10252(7) 0.63903(9) 0.0437(2) 0.0333(4) Uani 1 1 d . . . H16 H 0.0916 0.6859 0.0356 0.040 Uiso 1 1 calc R . . N17 N 0.20632(6) 0.65274(7) 0.1876(2) 0.0314(3) Uani 1 1 d . . . H17 H 0.2140(7) 0.7000(11) 0.212(2) 0.038 Uiso 1 1 d . . . C18 C 0.24618(8) 0.60439(8) 0.2349(2) 0.0328(4) Uani 1 1 d . . . H18 H 0.2842 0.6150 0.2890 0.039 Uiso 1 1 calc R . . N19 N 0.22787(6) 0.54089(7) 0.1996(2) 0.0309(3) Uani 1 1 d . . . C21 C 0.24764(7) 0.34730(7) 0.2252(2) 0.0227(3) Uani 1 1 d . . . O21 O 0.26869(5) 0.29023(5) 0.26285(17) 0.0317(3) Uani 1 1 d . . . C31 C 0.14927(6) 0.30807(8) 0.1501(2) 0.0227(3) Uani 1 1 d . . . N31 N 0.19169(5) 0.35800(7) 0.16543(19) 0.0246(3) Uani 1 1 d . . . H31 H 0.1806(7) 0.4002(9) 0.132(2) 0.030 Uiso 1 1 d . . . C32 C 0.09770(7) 0.32340(8) 0.0312(2) 0.0263(3) Uani 1 1 d . . . H32 H 0.0930 0.3648 -0.0435 0.032 Uiso 1 1 calc R . . C33 C 0.05308(7) 0.27925(9) 0.0198(2) 0.0316(4) Uani 1 1 d . . . H33 H 0.0177 0.2908 -0.0598 0.038 Uiso 1 1 calc R . . C34 C 0.05995(7) 0.21794(8) 0.1248(2) 0.0310(4) Uani 1 1 d . . . H34 H 0.0295 0.1871 0.1162 0.037 Uiso 1 1 calc R . . C35 C 0.11125(7) 0.20214(8) 0.2413(2) 0.0278(4) Uani 1 1 d . . . H35 H 0.1161 0.1600 0.3124 0.033 Uiso 1 1 calc R . . C36 C 0.15601(7) 0.24682(8) 0.2565(2) 0.0247(3) Uani 1 1 d . . . H36 H 0.1911 0.2357 0.3391 0.030 Uiso 1 1 calc R . . C41 C 0.33650(6) 0.40841(8) 0.3133(2) 0.0220(3) Uani 1 1 d . . . N41 N 0.27844(5) 0.40586(7) 0.23966(19) 0.0249(3) Uani 1 1 d . . . H41 H 0.2599(7) 0.4474(9) 0.229(2) 0.030 Uiso 1 1 d . . . C42 C 0.35761(6) 0.46212(8) 0.4409(2) 0.0255(3) Uani 1 1 d . . . H42 H 0.3328 0.4946 0.4779 0.031 Uiso 1 1 calc R . . C43 C 0.41431(7) 0.46845(8) 0.5138(2) 0.0281(4) Uani 1 1 d . . . H43 H 0.4283 0.5054 0.5998 0.034 Uiso 1 1 calc R . . C44 C 0.45080(7) 0.42120(8) 0.4621(2) 0.0271(4) Uani 1 1 d . . . H44 H 0.4898 0.4251 0.5138 0.033 Uiso 1 1 calc R . . C45 C 0.42999(7) 0.36815(8) 0.3346(2) 0.0273(4) Uani 1 1 d . . . H45 H 0.4550 0.3357 0.2988 0.033 Uiso 1 1 calc R . . C46 C 0.37327(7) 0.36160(8) 0.2584(2) 0.0249(3) Uani 1 1 d . . . H46 H 0.3595 0.3254 0.1690 0.030 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 C11 0.0379(11) 0.0326(10) 0.0378(9) 0.0062(7) 0.0119(8) 0.0054(8) C12 0.0362(11) 0.0281(10) 0.0374(8) 0.0026(7) 0.0087(8) -0.0010(7) N13 0.0341(9) 0.0219(7) 0.0365(7) 0.0017(6) 0.0080(6) -0.0024(6) C14 0.0337(10) 0.0195(8) 0.0290(7) 0.0025(6) 0.0113(7) 0.0004(6) C15 0.0393(10) 0.0184(8) 0.0299(8) 0.0024(6) 0.0158(7) -0.0001(7) C16 0.0428(11) 0.0229(9) 0.0386(9) 0.0078(7) 0.0184(8) 0.0085(7) N17 0.0415(9) 0.0169(7) 0.0378(7) 0.0001(6) 0.0128(7) -0.0003(6) C18 0.0393(11) 0.0222(9) 0.0376(8) 0.0014(7) 0.0102(8) -0.0010(7) N19 0.0355(9) 0.0183(7) 0.0395(7) 0.0006(6) 0.0092(6) 0.0004(6) C21 0.0257(9) 0.0176(8) 0.0249(7) -0.0001(6) 0.0058(6) -0.0009(6) O21 0.0280(7) 0.0159(6) 0.0507(7) 0.0029(5) 0.0073(5) 0.0012(5) C31 0.0241(9) 0.0192(8) 0.0253(7) -0.0038(6) 0.0068(6) -0.0021(6) N31 0.0236(8) 0.0157(7) 0.0342(7) 0.0032(5) 0.0051(6) 0.0002(5) C32 0.0282(9) 0.0230(8) 0.0274(7) -0.0004(6) 0.0053(7) 0.0008(6) C33 0.0266(9) 0.0343(10) 0.0322(8) -0.0045(7) 0.0025(7) -0.0025(7) C34 0.0323(10) 0.0266(9) 0.0356(8) -0.0052(7) 0.0106(7) -0.0082(7) C35 0.0317(10) 0.0225(8) 0.0304(7) -0.0001(7) 0.0090(7) -0.0040(7) C36 0.0271(9) 0.0207(8) 0.0264(7) -0.0001(6) 0.0059(6) -0.0014(6) C41 0.0224(8) 0.0173(8) 0.0263(7) 0.0029(6) 0.0051(6) -0.0016(6) N41 0.0239(7) 0.0142(7) 0.0357(7) -0.0001(5) 0.0045(6) 0.0001(5) C42 0.0289(9) 0.0190(8) 0.0300(7) -0.0023(6) 0.0097(7) -0.0007(6) C43 0.0314(10) 0.0231(8) 0.0300(7) -0.0019(7) 0.0073(7) -0.0063(7) C44 0.0236(9) 0.0253(9) 0.0321(8) 0.0050(7) 0.0048(6) -0.0039(6) C45 0.0275(9) 0.0241(9) 0.0327(8) 0.0023(6) 0.0113(7) 0.0023(6) C46 0.0281(9) 0.0193(8) 0.0279(7) -0.0016(6) 0.0076(7) -0.0012(6) _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 C11 C16 1.383(2) . ? C11 C12 1.394(2) . ? C11 H11 0.9500 . ? C12 N13 1.336(2) . ? C12 H12 0.9500 . ? N13 C14 1.336(2) . ? C14 N19 1.382(2) . ? C14 C15 1.402(2) . ? C15 N17 1.375(2) . ? C15 C16 1.376(2) . ? C16 H16 0.9500 . ? N17 C18 1.346(2) . ? N17 H17 0.95(2) . ? C18 N19 1.320(2) . ? C18 H18 0.9500 . ? C21 O21 1.2290(17) . ? C21 N41 1.3592(19) . ? C21 N31 1.361(2) . ? C31 C32 1.385(2) . ? C31 C36 1.392(2) . ? C31 N31 1.4106(19) . ? N31 H31 0.881(18) . ? C32 C33 1.380(2) . ? C32 H32 0.9500 . ? C33 C34 1.388(2) . ? C33 H33 0.9500 . ? C34 C35 1.375(2) . ? C34 H34 0.9500 . ? C35 C36 1.386(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.390(2) . ? C41 C42 1.394(2) . ? C41 N41 1.4059(19) . ? N41 H41 0.924(18) . ? C42 C43 1.379(2) . ? C42 H42 0.9500 . ? C43 C44 1.382(2) . ? C43 H43 0.9500 . ? C44 C45 1.382(2) . ? C44 H44 0.9500 . ? C45 C46 1.383(2) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? 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 C16 C11 C12 120.38(17) . . ? C16 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? N13 C12 C11 124.98(16) . . ? N13 C12 H12 117.5 . . ? C11 C12 H12 117.5 . . ? C14 N13 C12 114.03(14) . . ? N13 C14 N19 124.64(14) . . ? N13 C14 C15 124.75(15) . . ? N19 C14 C15 110.62(14) . . ? N17 C15 C16 134.87(15) . . ? N17 C15 C14 104.71(14) . . ? C16 C15 C14 120.42(15) . . ? C15 C16 C11 115.45(16) . . ? C15 C16 H16 122.3 . . ? C11 C16 H16 122.3 . . ? C18 N17 C15 106.92(14) . . ? C18 N17 H17 122.1(11) . . ? C15 N17 H17 130.9(11) . . ? N19 C18 N17 114.18(16) . . ? N19 C18 H18 122.9 . . ? N17 C18 H18 122.9 . . ? C18 N19 C14 103.56(13) . . ? O21 C21 N41 122.76(15) . . ? O21 C21 N31 123.56(14) . . ? N41 C21 N31 113.69(13) . . ? C32 C31 C36 119.21(14) . . ? C32 C31 N31 117.44(14) . . ? C36 C31 N31 123.24(14) . . ? C21 N31 C31 126.58(13) . . ? C21 N31 H31 117.2(11) . . ? C31 N31 H31 116.2(11) . . ? C33 C32 C31 120.75(15) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C34 119.99(16) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C35 C34 C33 119.45(15) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 120.92(15) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? C35 C36 C31 119.67(15) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C46 C41 C42 119.31(14) . . ? C46 C41 N41 122.88(13) . . ? C42 C41 N41 117.76(13) . . ? C21 N41 C41 124.03(13) . . ? C21 N41 H41 118.2(10) . . ? C41 N41 H41 116.2(10) . . ? C43 C42 C41 120.46(14) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C42 C43 C44 120.24(15) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? C43 C44 C45 119.40(15) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C44 C45 C46 121.02(15) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? C45 C46 C41 119.54(14) . . ? C45 C46 H46 120.2 . . ? C41 C46 H46 120.2 . . ? 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 C16 C11 C12 N13 0.0(3) . . . . ? C11 C12 N13 C14 0.3(2) . . . . ? C12 N13 C14 N19 179.64(13) . . . . ? C12 N13 C14 C15 -0.3(2) . . . . ? N13 C14 C15 N17 -179.95(14) . . . . ? N19 C14 C15 N17 0.13(17) . . . . ? N13 C14 C15 C16 -0.1(2) . . . . ? N19 C14 C15 C16 -179.97(13) . . . . ? N17 C15 C16 C11 -179.80(16) . . . . ? C14 C15 C16 C11 0.3(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C16 C15 N17 C18 179.92(17) . . . . ? C14 C15 N17 C18 -0.21(17) . . . . ? C15 N17 C18 N19 0.23(19) . . . . ? N17 C18 N19 C14 -0.14(18) . . . . ? N13 C14 N19 C18 -179.92(14) . . . . ? C15 C14 N19 C18 0.00(17) . . . . ? O21 C21 N31 C31 4.6(2) . . . . ? N41 C21 N31 C31 -175.37(13) . . . . ? C32 C31 N31 C21 -160.33(14) . . . . ? C36 C31 N31 C21 23.4(2) . . . . ? C36 C31 C32 C33 1.0(2) . . . . ? N31 C31 C32 C33 -175.41(14) . . . . ? C31 C32 C33 C34 -1.5(2) . . . . ? C32 C33 C34 C35 0.7(2) . . . . ? C33 C34 C35 C36 0.5(2) . . . . ? C34 C35 C36 C31 -1.0(2) . . . . ? C32 C31 C36 C35 0.3(2) . . . . ? N31 C31 C36 C35 176.43(14) . . . . ? O21 C21 N41 C41 -5.3(2) . . . . ? N31 C21 N41 C41 174.74(12) . . . . ? C46 C41 N41 C21 45.1(2) . . . . ? C42 C41 N41 C21 -137.48(15) . . . . ? C46 C41 C42 C43 -0.7(2) . . . . ? N41 C41 C42 C43 -178.24(13) . . . . ? C41 C42 C43 C44 -0.5(2) . . . . ? C42 C43 C44 C45 0.9(2) . . . . ? C43 C44 C45 C46 -0.1(2) . . . . ? C44 C45 C46 C41 -1.1(2) . . . . ? C42 C41 C46 C45 1.5(2) . . . . ? N41 C41 C46 C45 178.88(13) . . . . ? 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 N31 H31 N13 0.881(18) 2.196(19) 3.061(2) 167.0(15) . N41 H41 N19 0.924(18) 1.974(18) 2.8942(19) 173.5(15) . N17 H17 O21 0.95(2) 1.81(2) 2.7508(18) 174.7(16) 4 _diffrn_measured_fraction_theta_max 0.797 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.212 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 937212' ####################################################################### # # 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_ke1201m _audit_creation_method SHELXL-97 _chemical_name_systematic ; KEDP5 3H-imidazo[4,5-b]pyridine, 1,4-diiodotetrafluorobenzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H5 N3) (C6 F4 I2) ; _chemical_formula_sum 'C12 H5 F4 I2 N3' _chemical_formula_weight 520.99 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 13.0356(7) _cell_length_b 23.2353(13) _cell_length_c 9.7061(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.229(2) _cell_angle_gamma 90.00 _cell_volume 2836.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 31.70 _exptl_crystal_description prism _exptl_crystal_colour bronze _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 4.475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4997 _exptl_absorpt_correction_T_max 0.8413 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25846 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 31.76 _reflns_number_total 8706 _reflns_number_gt 6561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8706 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 N11 N 0.4650(5) 0.0723(2) 0.3356(7) 0.0290(12) Uani 1 1 d . . . C12 C 0.3969(5) 0.0509(3) 0.4015(8) 0.0278(14) Uani 1 1 d . . . H12 H 0.3872 0.0108 0.4124 0.033 Uiso 1 1 calc R . . N13 N 0.3419(4) 0.0918(2) 0.4525(7) 0.0251(11) Uani 1 1 d . . . H13 H 0.2928 0.0860 0.4983 0.030 Uiso 1 1 calc R . . C14 C 0.3780(5) 0.1438(3) 0.4188(7) 0.0226(12) Uani 1 1 d . . . N15 N 0.3483(4) 0.1957(2) 0.4509(6) 0.0248(11) Uani 1 1 d . . . C16 C 0.3977(6) 0.2392(3) 0.4028(9) 0.0288(15) Uani 1 1 d . . . H16 H 0.3808 0.2774 0.4241 0.035 Uiso 1 1 calc R . . C17 C 0.4714(6) 0.2320(3) 0.3244(9) 0.0323(16) Uani 1 1 d . . . H17 H 0.5014 0.2649 0.2919 0.039 Uiso 1 1 calc R . . C18 C 0.5022(6) 0.1774(3) 0.2923(8) 0.0302(15) Uani 1 1 d . . . H18 H 0.5535 0.1719 0.2397 0.036 Uiso 1 1 calc R . . C19 C 0.4535(5) 0.1310(3) 0.3418(8) 0.0241(12) Uani 1 1 d . . . N21 N 0.0836(5) 0.2107(2) 0.7487(7) 0.0260(12) Uani 1 1 d . . . C22 C 0.1552(6) 0.2317(3) 0.6902(8) 0.0282(14) Uani 1 1 d . . . H22 H 0.1736 0.2714 0.6951 0.034 Uiso 1 1 calc R . . N23 N 0.2012(4) 0.1924(2) 0.6220(7) 0.0251(11) Uani 1 1 d . . . H23 H 0.2512 0.1987 0.5781 0.030 Uiso 1 1 calc R . . C24 C 0.1538(5) 0.1407(3) 0.6354(8) 0.0241(13) Uani 1 1 d . . . N25 N 0.1758(4) 0.0896(2) 0.5901(7) 0.0236(11) Uani 1 1 d . . . C26 C 0.1153(5) 0.0464(3) 0.6193(8) 0.0252(13) Uani 1 1 d . . . H26 H 0.1243 0.0091 0.5842 0.030 Uiso 1 1 calc R . . C27 C 0.0408(6) 0.0533(3) 0.6975(8) 0.0272(14) Uani 1 1 d . . . H27 H 0.0023 0.0208 0.7166 0.033 Uiso 1 1 calc R . . C28 C 0.0220(5) 0.1075(3) 0.7485(8) 0.0268(13) Uani 1 1 d . . . H28 H -0.0280 0.1131 0.8031 0.032 Uiso 1 1 calc R . . C29 C 0.0802(5) 0.1525(3) 0.7148(7) 0.0224(12) Uani 1 1 d . . . C31 C 0.6945(5) -0.0185(3) 0.0759(8) 0.0228(12) Uani 1 1 d . . . I1 I 0.59881(3) 0.019526(17) 0.19333(5) 0.02427(11) Uani 1 1 d . . . C32 C 0.7681(5) 0.0139(3) 0.0290(7) 0.0225(12) Uani 1 1 d . . . F32 F 0.7784(3) 0.07040(16) 0.0567(5) 0.0292(9) Uani 1 1 d . . . C33 C 0.8287(5) -0.0108(3) -0.0525(8) 0.0233(13) Uani 1 1 d . . . F33 F 0.8964(3) 0.02296(16) -0.0982(5) 0.0308(9) Uani 1 1 d . . . C34 C 0.8241(5) -0.0685(3) -0.0814(7) 0.0230(12) Uani 1 1 d . . . I2 I 0.92603(4) -0.106872(18) -0.18768(5) 0.02763(12) Uani 1 1 d . . . C35 C 0.7531(5) -0.1012(3) -0.0323(8) 0.0240(13) Uani 1 1 d . . . F35 F 0.7453(3) -0.15821(16) -0.0549(5) 0.0303(9) Uani 1 1 d . . . C36 C 0.6891(5) -0.0763(3) 0.0437(8) 0.0255(13) Uani 1 1 d . . . F36 F 0.6220(3) -0.11001(16) 0.0906(5) 0.0323(10) Uani 1 1 d . . . C41 C -0.1743(5) 0.3052(3) 0.9535(7) 0.0231(12) Uani 1 1 d . . . I3 I -0.06454(3) 0.267121(17) 0.85852(5) 0.02455(11) Uani 1 1 d . . . C42 C -0.2375(6) 0.2719(2) 1.0163(8) 0.0270(14) Uani 1 1 d . . . F42 F -0.2391(3) 0.21468(16) 1.0009(5) 0.0324(10) Uani 1 1 d . . . C43 C -0.3017(5) 0.2961(3) 1.0938(8) 0.0239(12) Uani 1 1 d . . . F43 F -0.3593(3) 0.26161(17) 1.1527(5) 0.0315(9) Uani 1 1 d . . . C44 C -0.3040(5) 0.3551(3) 1.1110(8) 0.0237(12) Uani 1 1 d . . . I4 I -0.39844(3) 0.391302(18) 1.23066(5) 0.02741(12) Uani 1 1 d . . . C45 C -0.2423(5) 0.3885(2) 1.0477(8) 0.0239(13) Uani 1 1 d . . . F45 F -0.2403(3) 0.44630(16) 1.0644(5) 0.0297(9) Uani 1 1 d . . . C46 C -0.1796(5) 0.3641(3) 0.9681(8) 0.0249(13) Uani 1 1 d . . . F46 F -0.1200(3) 0.39921(16) 0.9114(5) 0.0313(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.031(3) 0.020(2) 0.042(4) -0.004(2) 0.021(3) 0.002(2) C12 0.032(3) 0.015(2) 0.044(4) -0.005(3) 0.024(3) -0.002(2) N13 0.025(3) 0.019(2) 0.037(3) -0.001(2) 0.018(2) -0.0004(18) C14 0.026(3) 0.019(2) 0.026(3) -0.001(2) 0.013(3) -0.001(2) N15 0.027(3) 0.019(2) 0.033(3) 0.005(2) 0.017(2) 0.0029(19) C16 0.033(3) 0.014(2) 0.044(4) 0.005(3) 0.019(3) 0.001(2) C17 0.038(4) 0.023(3) 0.044(4) 0.009(3) 0.024(3) -0.003(3) C18 0.030(3) 0.031(3) 0.037(4) 0.001(3) 0.021(3) -0.004(3) C19 0.024(3) 0.024(3) 0.028(3) 0.000(2) 0.012(3) 0.002(2) N21 0.033(3) 0.023(2) 0.029(3) 0.000(2) 0.020(3) 0.004(2) C22 0.037(4) 0.019(3) 0.036(4) -0.001(3) 0.021(3) 0.004(2) N23 0.027(3) 0.018(2) 0.036(3) -0.001(2) 0.019(3) 0.0001(19) C24 0.022(3) 0.020(3) 0.036(4) 0.007(2) 0.016(3) 0.004(2) N25 0.029(3) 0.018(2) 0.029(3) 0.003(2) 0.017(2) 0.0025(18) C26 0.027(3) 0.021(3) 0.032(4) 0.000(2) 0.016(3) 0.000(2) C27 0.032(3) 0.023(3) 0.031(4) 0.005(3) 0.018(3) 0.000(2) C28 0.027(3) 0.027(3) 0.033(4) 0.002(3) 0.018(3) 0.000(2) C29 0.023(3) 0.022(3) 0.028(3) 0.003(2) 0.017(3) 0.003(2) C31 0.020(3) 0.023(3) 0.028(3) 0.001(2) 0.012(3) 0.002(2) I1 0.0255(2) 0.02234(18) 0.0295(2) -0.00196(15) 0.01527(17) 0.00134(14) C32 0.024(3) 0.022(3) 0.026(3) 0.003(2) 0.014(3) 0.005(2) F32 0.036(2) 0.0177(16) 0.039(2) -0.0028(16) 0.0193(19) -0.0001(14) C33 0.025(3) 0.021(3) 0.030(3) 0.001(2) 0.018(3) -0.001(2) F33 0.038(2) 0.0221(17) 0.042(3) 0.0002(17) 0.027(2) -0.0039(15) C34 0.022(3) 0.025(3) 0.026(3) -0.002(2) 0.012(3) 0.000(2) I2 0.0301(2) 0.0252(2) 0.0343(3) -0.00390(17) 0.02037(19) -0.00032(15) C35 0.026(3) 0.017(2) 0.035(4) 0.002(2) 0.019(3) 0.006(2) F35 0.037(2) 0.0167(16) 0.044(3) 0.0004(16) 0.023(2) 0.0008(14) C36 0.025(3) 0.021(3) 0.036(4) 0.005(3) 0.018(3) 0.001(2) F36 0.034(2) 0.0238(18) 0.048(3) 0.0000(17) 0.028(2) -0.0021(15) C41 0.023(3) 0.019(3) 0.030(3) -0.004(2) 0.012(3) -0.001(2) I3 0.0260(2) 0.02249(18) 0.0293(2) -0.00325(16) 0.01446(17) -0.00024(14) C42 0.033(3) 0.013(2) 0.038(4) -0.004(2) 0.014(3) -0.003(2) F42 0.040(2) 0.0159(16) 0.049(3) -0.0021(17) 0.025(2) -0.0019(15) C43 0.022(3) 0.026(3) 0.028(3) 0.000(3) 0.013(3) -0.004(2) F43 0.033(2) 0.0249(18) 0.045(3) 0.0006(17) 0.024(2) -0.0051(15) C44 0.025(3) 0.021(3) 0.030(3) -0.002(2) 0.014(3) 0.002(2) I4 0.0297(2) 0.0247(2) 0.0334(3) -0.00097(16) 0.01804(19) 0.00184(14) C45 0.028(3) 0.016(2) 0.030(4) 0.002(2) 0.013(3) 0.001(2) F45 0.034(2) 0.0167(16) 0.044(3) -0.0004(16) 0.0189(19) -0.0004(14) C46 0.024(3) 0.023(3) 0.032(4) 0.001(3) 0.014(3) -0.004(2) F46 0.038(2) 0.0213(17) 0.043(3) 0.0000(17) 0.026(2) -0.0036(15) _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 N11 C12 1.320(8) . ? N11 C19 1.376(8) . ? C12 N13 1.360(8) . ? C12 H12 0.9500 . ? N13 C14 1.367(8) . ? N13 H13 0.8800 . ? C14 N15 1.329(8) . ? C14 C19 1.415(8) . ? N15 C16 1.346(8) . ? C16 C17 1.384(10) . ? C16 H16 0.9500 . ? C17 C18 1.390(10) . ? C17 H17 0.9500 . ? C18 C19 1.399(9) . ? C18 H18 0.9500 . ? N21 C22 1.308(8) . ? N21 C29 1.389(8) . ? C22 N23 1.356(8) . ? C22 H22 0.9500 . ? N23 C24 1.372(8) . ? N23 H23 0.8800 . ? C24 N25 1.323(8) . ? C24 C29 1.407(8) . ? N25 C26 1.351(8) . ? C26 C27 1.391(9) . ? C26 H26 0.9500 . ? C27 C28 1.400(9) . ? C27 H27 0.9500 . ? C28 C29 1.380(8) . ? C28 H28 0.9500 . ? C31 C36 1.377(9) . ? C31 C32 1.386(8) . ? C31 I1 2.094(6) . ? C32 F32 1.340(7) . ? C32 C33 1.381(8) . ? C33 F33 1.341(7) . ? C33 C34 1.369(9) . ? C34 C35 1.376(8) . ? C34 I2 2.084(6) . ? C35 F35 1.343(7) . ? C35 C36 1.377(8) . ? C36 F36 1.340(7) . ? C41 C46 1.380(9) . ? C41 C42 1.383(9) . ? C41 I3 2.091(6) . ? C42 F42 1.338(7) . ? C42 C43 1.383(9) . ? C43 F43 1.326(7) . ? C43 C44 1.383(9) . ? C44 C45 1.372(9) . ? C44 I4 2.079(6) . ? C45 F45 1.352(7) . ? C45 C46 1.385(9) . ? C46 F46 1.340(7) . ? 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 C12 N11 C19 104.8(5) . . ? N11 C12 N13 113.6(5) . . ? N11 C12 H12 123.2 . . ? N13 C12 H12 123.2 . . ? C12 N13 C14 106.5(5) . . ? C12 N13 H13 126.8 . . ? C14 N13 H13 126.8 . . ? N15 C14 N13 127.3(6) . . ? N15 C14 C19 127.0(6) . . ? N13 C14 C19 105.7(5) . . ? C14 N15 C16 113.8(5) . . ? N15 C16 C17 124.4(6) . . ? N15 C16 H16 117.8 . . ? C17 C16 H16 117.8 . . ? C16 C17 C18 121.1(6) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C19 116.3(6) . . ? C17 C18 H18 121.9 . . ? C19 C18 H18 121.9 . . ? N11 C19 C18 133.2(6) . . ? N11 C19 C14 109.4(5) . . ? C18 C19 C14 117.4(6) . . ? C22 N21 C29 104.1(5) . . ? N21 C22 N23 114.7(6) . . ? N21 C22 H22 122.7 . . ? N23 C22 H22 122.7 . . ? C22 N23 C24 106.0(5) . . ? C22 N23 H23 127.0 . . ? C24 N23 H23 127.0 . . ? N25 C24 N23 127.7(6) . . ? N25 C24 C29 126.5(6) . . ? N23 C24 C29 105.7(5) . . ? C24 N25 C26 114.1(5) . . ? N25 C26 C27 124.0(6) . . ? N25 C26 H26 118.0 . . ? C27 C26 H26 118.0 . . ? C26 C27 C28 120.5(6) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C29 C28 C27 116.1(6) . . ? C29 C28 H28 121.9 . . ? C27 C28 H28 121.9 . . ? C28 C29 N21 131.8(6) . . ? C28 C29 C24 118.6(6) . . ? N21 C29 C24 109.6(5) . . ? C36 C31 C32 117.0(6) . . ? C36 C31 I1 122.2(5) . . ? C32 C31 I1 120.8(4) . . ? F32 C32 C33 118.7(5) . . ? F32 C32 C31 120.5(5) . . ? C33 C32 C31 120.8(6) . . ? F33 C33 C34 120.1(5) . . ? F33 C33 C32 118.2(5) . . ? C34 C33 C32 121.6(6) . . ? C33 C34 C35 117.8(5) . . ? C33 C34 I2 121.4(4) . . ? C35 C34 I2 120.7(5) . . ? F35 C35 C36 118.1(5) . . ? F35 C35 C34 121.0(5) . . ? C36 C35 C34 120.8(6) . . ? F36 C36 C35 118.5(5) . . ? F36 C36 C31 119.5(6) . . ? C35 C36 C31 121.9(6) . . ? C46 C41 C42 117.2(6) . . ? C46 C41 I3 121.6(5) . . ? C42 C41 I3 120.9(4) . . ? F42 C42 C41 120.0(6) . . ? F42 C42 C43 118.1(6) . . ? C41 C42 C43 121.9(5) . . ? F43 C43 C42 118.8(6) . . ? F43 C43 C44 121.0(6) . . ? C42 C43 C44 120.2(6) . . ? C45 C44 C43 118.2(6) . . ? C45 C44 I4 121.6(4) . . ? C43 C44 I4 120.2(5) . . ? F45 C45 C44 120.2(6) . . ? F45 C45 C46 118.5(5) . . ? C44 C45 C46 121.3(5) . . ? F46 C46 C41 120.7(6) . . ? F46 C46 C45 118.1(5) . . ? C41 C46 C45 121.1(6) . . ? 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 C19 N11 C12 N13 -0.7(9) . . . . ? N11 C12 N13 C14 -0.8(9) . . . . ? C12 N13 C14 N15 -178.2(7) . . . . ? C12 N13 C14 C19 1.9(8) . . . . ? N13 C14 N15 C16 -179.8(7) . . . . ? C19 C14 N15 C16 0.0(11) . . . . ? C14 N15 C16 C17 1.2(11) . . . . ? N15 C16 C17 C18 -1.7(13) . . . . ? C16 C17 C18 C19 0.9(12) . . . . ? C12 N11 C19 C18 180.0(9) . . . . ? C12 N11 C19 C14 2.0(8) . . . . ? C17 C18 C19 N11 -177.7(8) . . . . ? C17 C18 C19 C14 0.2(11) . . . . ? N15 C14 C19 N11 177.7(7) . . . . ? N13 C14 C19 N11 -2.5(8) . . . . ? N15 C14 C19 C18 -0.7(11) . . . . ? N13 C14 C19 C18 179.2(7) . . . . ? C29 N21 C22 N23 -1.0(9) . . . . ? N21 C22 N23 C24 1.0(9) . . . . ? C22 N23 C24 N25 -177.3(7) . . . . ? C22 N23 C24 C29 -0.5(8) . . . . ? N23 C24 N25 C26 179.9(7) . . . . ? C29 C24 N25 C26 3.7(11) . . . . ? C24 N25 C26 C27 -3.8(11) . . . . ? N25 C26 C27 C28 1.8(12) . . . . ? C26 C27 C28 C29 0.7(11) . . . . ? C27 C28 C29 N21 -178.7(7) . . . . ? C27 C28 C29 C24 -1.0(11) . . . . ? C22 N21 C29 C28 178.5(8) . . . . ? C22 N21 C29 C24 0.6(8) . . . . ? N25 C24 C29 C28 -1.4(12) . . . . ? N23 C24 C29 C28 -178.3(7) . . . . ? N25 C24 C29 N21 176.8(7) . . . . ? N23 C24 C29 N21 -0.1(8) . . . . ? C36 C31 C32 F32 -179.7(6) . . . . ? I1 C31 C32 F32 -0.8(9) . . . . ? C36 C31 C32 C33 3.3(11) . . . . ? I1 C31 C32 C33 -177.8(5) . . . . ? F32 C32 C33 F33 1.1(10) . . . . ? C31 C32 C33 F33 178.2(6) . . . . ? F32 C32 C33 C34 178.1(6) . . . . ? C31 C32 C33 C34 -4.8(11) . . . . ? F33 C33 C34 C35 -179.9(6) . . . . ? C32 C33 C34 C35 3.1(11) . . . . ? F33 C33 C34 I2 2.9(10) . . . . ? C32 C33 C34 I2 -174.0(5) . . . . ? C33 C34 C35 F35 -179.1(7) . . . . ? I2 C34 C35 F35 -1.9(10) . . . . ? C33 C34 C35 C36 -0.2(11) . . . . ? I2 C34 C35 C36 177.0(6) . . . . ? F35 C35 C36 F36 -0.4(10) . . . . ? C34 C35 C36 F36 -179.3(7) . . . . ? F35 C35 C36 C31 177.8(7) . . . . ? C34 C35 C36 C31 -1.1(12) . . . . ? C32 C31 C36 F36 177.7(6) . . . . ? I1 C31 C36 F36 -1.2(10) . . . . ? C32 C31 C36 C35 -0.4(11) . . . . ? I1 C31 C36 C35 -179.3(6) . . . . ? C46 C41 C42 F42 177.3(7) . . . . ? I3 C41 C42 F42 -8.6(10) . . . . ? C46 C41 C42 C43 -1.6(11) . . . . ? I3 C41 C42 C43 172.5(6) . . . . ? F42 C42 C43 F43 2.0(10) . . . . ? C41 C42 C43 F43 -179.1(7) . . . . ? F42 C42 C43 C44 -179.1(7) . . . . ? C41 C42 C43 C44 -0.2(11) . . . . ? F43 C43 C44 C45 179.8(6) . . . . ? C42 C43 C44 C45 0.9(11) . . . . ? F43 C43 C44 I4 0.0(10) . . . . ? C42 C43 C44 I4 -178.9(6) . . . . ? C43 C44 C45 F45 -178.5(6) . . . . ? I4 C44 C45 F45 1.2(10) . . . . ? C43 C44 C45 C46 0.3(11) . . . . ? I4 C44 C45 C46 180.0(5) . . . . ? C42 C41 C46 F46 179.4(7) . . . . ? I3 C41 C46 F46 5.4(10) . . . . ? C42 C41 C46 C45 2.7(11) . . . . ? I3 C41 C46 C45 -171.3(5) . . . . ? F45 C45 C46 F46 -0.1(10) . . . . ? C44 C45 C46 F46 -178.9(7) . . . . ? F45 C45 C46 C41 176.7(6) . . . . ? C44 C45 C46 C41 -2.1(11) . . . . ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 4.412 _refine_diff_density_min -1.447 _refine_diff_density_rms 0.287 _database_code_depnum_ccdc_archive 'CCDC 937213' ####################################################################### # # 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_ke1203m _audit_creation_method SHELXL-97 _chemical_name_systematic ; KEDPU7 3H-imidazo[4,5-b]pyridine, N-phenyl-N-(4-bromophenyl)-urea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H5 N3) (C13 H11 Br N2 O) ; _chemical_formula_sum 'C19 H16 Br N5 O' _chemical_formula_weight 410.28 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' Br Br -0.2901 2.4595 '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 13.5679(17) _cell_length_b 18.536(3) _cell_length_c 6.9157(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.335(7) _cell_angle_gamma 90.00 _cell_volume 1736.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5521 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 30.80 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5712 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26024 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5191 _reflns_number_gt 3484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+8.0000P] 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 5191 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.2119 _refine_ls_wR_factor_gt 0.1932 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Br1 Br 0.93486(4) 0.32568(3) 0.07429(8) 0.03208(18) Uani 1 1 d . . . N11 N 0.3964(3) 0.0915(2) 0.2416(6) 0.0238(8) Uani 1 1 d . . . H11 H 0.409(4) 0.048(4) 0.256(9) 0.029 Uiso 1 1 d . . . C12 C 0.4646(4) 0.1441(3) 0.2350(7) 0.0226(9) Uani 1 1 d . . . H12 H 0.5331 0.1346 0.2282 0.027 Uiso 1 1 calc R . . N13 N 0.4279(3) 0.2100(2) 0.2390(6) 0.0253(9) Uani 1 1 d . . . C14 C 0.3279(4) 0.1991(2) 0.2492(7) 0.0214(9) Uani 1 1 d . . . N15 N 0.2609(3) 0.2519(2) 0.2564(6) 0.0251(8) Uani 1 1 d . . . C16 C 0.1689(4) 0.2288(3) 0.2640(7) 0.0284(10) Uani 1 1 d . . . H16 H 0.1188 0.2641 0.2736 0.034 Uiso 1 1 calc R . . C17 C 0.1398(4) 0.1562(3) 0.2590(8) 0.0291(11) Uani 1 1 d . . . H17 H 0.0718 0.1441 0.2606 0.035 Uiso 1 1 calc R . . C18 C 0.2094(4) 0.1023(3) 0.2518(7) 0.0271(10) Uani 1 1 d . . . H18 H 0.1918 0.0527 0.2486 0.032 Uiso 1 1 calc R . . C19 C 0.3065(4) 0.1250(3) 0.2494(6) 0.0222(9) Uani 1 1 d . . . C21 C 0.4456(4) 0.4147(2) 0.2419(6) 0.0202(9) Uani 1 1 d . . . O21 O 0.4818(3) 0.47620(18) 0.2425(5) 0.0258(7) Uani 1 1 d . . . C31 C 0.6005(3) 0.3513(3) 0.1852(7) 0.0201(9) Uani 1 1 d . . . N31 N 0.5008(3) 0.3543(2) 0.2201(6) 0.0215(8) Uani 1 1 d . . . H31 H 0.482(5) 0.320(4) 0.227(9) 0.026 Uiso 1 1 d . . . C32 C 0.6501(4) 0.4043(3) 0.0839(7) 0.0223(9) Uani 1 1 d . . . H32 H 0.6151 0.4457 0.0367 0.027 Uiso 1 1 calc R . . C33 C 0.7487(4) 0.3974(3) 0.0519(6) 0.0222(9) Uani 1 1 d . . . H33 H 0.7819 0.4341 -0.0145 0.027 Uiso 1 1 calc R . . C34 C 0.7997(4) 0.3358(3) 0.1179(7) 0.0237(9) Uani 1 1 d . . . C35 C 0.7516(4) 0.2822(3) 0.2152(7) 0.0232(9) Uani 1 1 d . . . H35 H 0.7862 0.2400 0.2578 0.028 Uiso 1 1 calc R . . C36 C 0.6536(4) 0.2902(2) 0.2500(7) 0.0216(9) Uani 1 1 d . . . H36 H 0.6213 0.2537 0.3192 0.026 Uiso 1 1 calc R . . C41 C 0.2772(4) 0.4540(2) 0.3053(6) 0.0204(9) Uani 1 1 d . . . N41 N 0.3486(3) 0.4018(2) 0.2628(6) 0.0218(8) Uani 1 1 d . . . H41 H 0.327(4) 0.358(4) 0.259(9) 0.026 Uiso 1 1 d . . . C42 C 0.2993(4) 0.5191(3) 0.3979(7) 0.0225(9) Uani 1 1 d . . . H42 H 0.3660 0.5315 0.4317 0.027 Uiso 1 1 calc R . . C43 C 0.2242(4) 0.5660(3) 0.4411(7) 0.0247(10) Uani 1 1 d . . . H43 H 0.2402 0.6102 0.5050 0.030 Uiso 1 1 calc R . . C44 C 0.1267(4) 0.5497(3) 0.3932(7) 0.0277(10) Uani 1 1 d . . . H44 H 0.0756 0.5820 0.4241 0.033 Uiso 1 1 calc R . . C45 C 0.1044(4) 0.4847(3) 0.2985(7) 0.0276(10) Uani 1 1 d . . . H45 H 0.0376 0.4726 0.2643 0.033 Uiso 1 1 calc R . . C46 C 0.1788(4) 0.4377(3) 0.2541(7) 0.0233(9) Uani 1 1 d . . . H46 H 0.1628 0.3939 0.1881 0.028 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 Br1 0.0249(3) 0.0387(3) 0.0330(3) 0.0019(2) 0.00478(18) 0.0027(2) N11 0.033(2) 0.0130(18) 0.026(2) -0.0008(15) 0.0016(16) 0.0010(16) C12 0.029(2) 0.017(2) 0.021(2) -0.0019(17) -0.0019(18) 0.0021(18) N13 0.031(2) 0.0159(19) 0.029(2) -0.0010(15) -0.0004(17) 0.0032(16) C14 0.031(2) 0.0123(19) 0.021(2) 0.0006(16) 0.0000(18) 0.0003(17) N15 0.030(2) 0.0178(19) 0.028(2) -0.0001(15) 0.0033(16) 0.0050(16) C16 0.034(3) 0.024(2) 0.027(2) -0.0021(19) 0.003(2) 0.005(2) C17 0.029(3) 0.031(3) 0.028(2) -0.006(2) 0.005(2) -0.005(2) C18 0.035(3) 0.023(2) 0.023(2) -0.0015(18) 0.0058(19) -0.003(2) C19 0.034(3) 0.015(2) 0.017(2) -0.0009(16) 0.0023(18) 0.0022(18) C21 0.028(2) 0.016(2) 0.0157(19) 0.0003(15) 0.0016(17) -0.0016(17) O21 0.0298(18) 0.0128(15) 0.0356(19) -0.0001(13) 0.0075(14) -0.0027(13) C31 0.024(2) 0.016(2) 0.020(2) -0.0030(16) 0.0008(17) -0.0005(17) N31 0.028(2) 0.0098(17) 0.028(2) 0.0006(15) 0.0050(16) -0.0015(15) C32 0.028(2) 0.017(2) 0.021(2) 0.0013(17) 0.0005(17) -0.0011(18) C33 0.031(2) 0.018(2) 0.017(2) 0.0000(16) -0.0002(17) -0.0006(18) C34 0.025(2) 0.025(2) 0.021(2) -0.0024(18) -0.0024(17) 0.0020(18) C35 0.032(2) 0.020(2) 0.017(2) 0.0028(16) -0.0003(18) 0.0023(18) C36 0.031(2) 0.015(2) 0.019(2) 0.0034(16) 0.0022(17) -0.0032(17) C41 0.027(2) 0.016(2) 0.019(2) 0.0004(16) 0.0041(17) 0.0028(17) N41 0.028(2) 0.0120(17) 0.0251(19) -0.0020(15) 0.0029(16) 0.0003(15) C42 0.030(2) 0.019(2) 0.018(2) -0.0001(16) 0.0010(17) 0.0011(18) C43 0.039(3) 0.017(2) 0.018(2) 0.0023(16) 0.0052(19) 0.0012(19) C44 0.034(3) 0.025(2) 0.026(2) 0.0025(19) 0.008(2) 0.007(2) C45 0.027(2) 0.031(3) 0.025(2) 0.0007(19) 0.0019(19) 0.002(2) C46 0.028(2) 0.021(2) 0.021(2) 0.0013(17) 0.0019(18) 0.0002(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 Br1 C34 1.886(5) . ? N11 C12 1.347(7) . ? N11 C19 1.372(7) . ? N11 H11 0.82(7) . ? C12 N13 1.320(6) . ? C12 H12 0.9500 . ? N13 C14 1.377(7) . ? C14 N15 1.338(6) . ? C14 C19 1.404(7) . ? N15 C16 1.323(7) . ? C16 C17 1.403(8) . ? C16 H16 0.9500 . ? C17 C18 1.377(8) . ? C17 H17 0.9500 . ? C18 C19 1.384(7) . ? C18 H18 0.9500 . ? C21 O21 1.241(6) . ? C21 N41 1.353(6) . ? C21 N31 1.360(6) . ? C31 N31 1.390(6) . ? C31 C36 1.401(7) . ? C31 C32 1.402(7) . ? N31 H31 0.69(7) . ? C32 C33 1.374(7) . ? C32 H32 0.9500 . ? C33 C34 1.397(7) . ? C33 H33 0.9500 . ? C34 C35 1.385(7) . ? C35 C36 1.372(7) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.392(7) . ? C41 C46 1.394(7) . ? C41 N41 1.412(6) . ? N41 H41 0.87(7) . ? C42 C43 1.383(7) . ? C42 H42 0.9500 . ? C43 C44 1.379(8) . ? C43 H43 0.9500 . ? C44 C45 1.396(8) . ? C44 H44 0.9500 . ? C45 C46 1.381(7) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? 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 C12 N11 C19 106.8(4) . . ? C12 N11 H11 124(4) . . ? C19 N11 H11 128(4) . . ? N13 C12 N11 114.0(5) . . ? N13 C12 H12 123.0 . . ? N11 C12 H12 123.0 . . ? C12 N13 C14 103.9(4) . . ? N15 C14 N13 124.6(4) . . ? N15 C14 C19 125.0(5) . . ? N13 C14 C19 110.3(4) . . ? C16 N15 C14 114.2(4) . . ? N15 C16 C17 125.1(5) . . ? N15 C16 H16 117.5 . . ? C17 C16 H16 117.5 . . ? C18 C17 C16 120.2(5) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 115.8(5) . . ? C17 C18 H18 122.1 . . ? C19 C18 H18 122.1 . . ? N11 C19 C18 135.4(5) . . ? N11 C19 C14 104.9(4) . . ? C18 C19 C14 119.6(5) . . ? O21 C21 N41 123.2(4) . . ? O21 C21 N31 122.5(4) . . ? N41 C21 N31 114.3(4) . . ? N31 C31 C36 117.6(4) . . ? N31 C31 C32 124.0(4) . . ? C36 C31 C32 118.3(4) . . ? C21 N31 C31 126.8(4) . . ? C21 N31 H31 123(6) . . ? C31 N31 H31 110(6) . . ? C33 C32 C31 120.9(4) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C32 C33 C34 119.5(4) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C35 C34 C33 120.4(5) . . ? C35 C34 Br1 119.8(4) . . ? C33 C34 Br1 119.8(4) . . ? C36 C35 C34 119.8(4) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C31 121.0(4) . . ? C35 C36 H36 119.5 . . ? C31 C36 H36 119.5 . . ? C42 C41 C46 118.8(4) . . ? C42 C41 N41 124.0(4) . . ? C46 C41 N41 117.2(4) . . ? C21 N41 C41 125.8(4) . . ? C21 N41 H41 119(4) . . ? C41 N41 H41 115(4) . . ? C43 C42 C41 120.2(5) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C44 C43 C42 121.3(5) . . ? C44 C43 H43 119.4 . . ? C42 C43 H43 119.4 . . ? C43 C44 C45 118.7(5) . . ? C43 C44 H44 120.7 . . ? C45 C44 H44 120.7 . . ? C46 C45 C44 120.5(5) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C41 120.6(5) . . ? C45 C46 H46 119.7 . . ? C41 C46 H46 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N11 C12 N13 0.4(6) . . . . ? N11 C12 N13 C14 0.1(5) . . . . ? C12 N13 C14 N15 179.9(5) . . . . ? C12 N13 C14 C19 -0.5(5) . . . . ? N13 C14 N15 C16 179.4(5) . . . . ? C19 C14 N15 C16 -0.1(7) . . . . ? C14 N15 C16 C17 -2.0(7) . . . . ? N15 C16 C17 C18 2.2(8) . . . . ? C16 C17 C18 C19 -0.2(7) . . . . ? C12 N11 C19 C18 177.3(5) . . . . ? C12 N11 C19 C14 -0.6(5) . . . . ? C17 C18 C19 N11 -179.4(5) . . . . ? C17 C18 C19 C14 -1.7(7) . . . . ? N15 C14 C19 N11 -179.7(4) . . . . ? N13 C14 C19 N11 0.7(5) . . . . ? N15 C14 C19 C18 1.9(7) . . . . ? N13 C14 C19 C18 -177.6(4) . . . . ? O21 C21 N31 C31 -3.9(7) . . . . ? N41 C21 N31 C31 176.1(4) . . . . ? C36 C31 N31 C21 152.2(5) . . . . ? C32 C31 N31 C21 -30.0(7) . . . . ? N31 C31 C32 C33 -178.9(4) . . . . ? C36 C31 C32 C33 -1.2(7) . . . . ? C31 C32 C33 C34 1.3(7) . . . . ? C32 C33 C34 C35 -0.2(7) . . . . ? C32 C33 C34 Br1 179.9(3) . . . . ? C33 C34 C35 C36 -1.1(7) . . . . ? Br1 C34 C35 C36 178.8(4) . . . . ? C34 C35 C36 C31 1.3(7) . . . . ? N31 C31 C36 C35 177.8(4) . . . . ? C32 C31 C36 C35 -0.1(7) . . . . ? O21 C21 N41 C41 -6.1(7) . . . . ? N31 C21 N41 C41 173.8(4) . . . . ? C42 C41 N41 C21 -24.0(7) . . . . ? C46 C41 N41 C21 157.5(4) . . . . ? C46 C41 C42 C43 1.2(7) . . . . ? N41 C41 C42 C43 -177.4(4) . . . . ? C41 C42 C43 C44 -0.3(7) . . . . ? C42 C43 C44 C45 -0.3(7) . . . . ? C43 C44 C45 C46 0.1(8) . . . . ? C44 C45 C46 C41 0.8(7) . . . . ? C42 C41 C46 C45 -1.4(7) . . . . ? N41 C41 C46 C45 177.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N31 H31 N13 0.69(7) 2.17(7) 2.857(6) 177(8) . N41 H41 N15 0.87(7) 2.16(7) 3.023(6) 175(6) . N11 H11 O21 0.82(7) 1.99(7) 2.701(5) 144(6) 2_645 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 2.802 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.142 _database_code_depnum_ccdc_archive 'CCDC 937214' ####################################################################### # # 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_ke1220m _audit_creation_method SHELXL-97 _chemical_name_systematic ; KEDPX2 3H-imidazo[4,5-b]pyridine, 1,2-diiodotetrafluorobenzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H5 N3) (C6 F4 I2) ; _chemical_formula_sum 'C12 H5 F4 I2 N3' _chemical_formula_weight 520.99 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 11.5283(11) _cell_length_b 14.7657(14) _cell_length_c 8.7953(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.886(3) _cell_angle_gamma 90.00 _cell_volume 1398.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9985 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 33.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 4.537 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4639 _exptl_absorpt_correction_T_max 0.7725 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19188 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 33.14 _reflns_number_total 5009 _reflns_number_gt 4227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5009 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 N11 N 0.2649(3) 0.4756(2) 0.3212(4) 0.0247(6) Uani 1 1 d . . . C12 C 0.1892(3) 0.5418(2) 0.3223(4) 0.0249(7) Uani 1 1 d . . . H12 H 0.1903 0.5993 0.2744 0.030 Uiso 1 1 calc R . . N13 N 0.1089(3) 0.52008(19) 0.3988(3) 0.0213(5) Uani 1 1 d . . . H13 H 0.0516 0.5553 0.4120 0.026 Uiso 1 1 calc R . . C14 C 0.1351(3) 0.4327(2) 0.4506(4) 0.0186(5) Uani 1 1 d . . . N15 N 0.0784(2) 0.38275(19) 0.5296(3) 0.0215(5) Uani 1 1 d . . . C16 C 0.1244(3) 0.2990(2) 0.5651(4) 0.0254(6) Uani 1 1 d . . . H16 H 0.0876 0.2598 0.6207 0.030 Uiso 1 1 calc R . . C17 C 0.2233(3) 0.2655(2) 0.5254(5) 0.0257(7) Uani 1 1 d . . . H17 H 0.2521 0.2056 0.5561 0.031 Uiso 1 1 calc R . . C18 C 0.2797(3) 0.3183(2) 0.4421(4) 0.0240(6) Uani 1 1 d . . . H18 H 0.3467 0.2963 0.4136 0.029 Uiso 1 1 calc R . . C19 C 0.2333(3) 0.4050(2) 0.4024(4) 0.0203(6) Uani 1 1 d . . . C21 C 0.6492(3) 0.4380(2) 0.2112(4) 0.0183(5) Uani 1 1 d . . . I1 I 0.486885(18) 0.463924(15) 0.26031(2) 0.02083(6) Uani 1 1 d . . . C22 C 0.6978(3) 0.3510(2) 0.2163(4) 0.0188(5) Uani 1 1 d . . . I2 I 0.61358(2) 0.235480(16) 0.26605(3) 0.02570(6) Uani 1 1 d . . . C23 C 0.8047(3) 0.3393(2) 0.1805(4) 0.0208(6) Uani 1 1 d . . . F23 F 0.8555(2) 0.25707(15) 0.1846(3) 0.0302(5) Uani 1 1 d . . . C24 C 0.8613(3) 0.4113(2) 0.1354(4) 0.0218(6) Uani 1 1 d . . . F24 F 0.96174(18) 0.39761(15) 0.0960(3) 0.0291(4) Uani 1 1 d . . . C25 C 0.8134(3) 0.4965(2) 0.1294(4) 0.0218(6) Uani 1 1 d . . . F25 F 0.8684(2) 0.56653(15) 0.0874(3) 0.0293(4) Uani 1 1 d . . . C26 C 0.7089(3) 0.5090(2) 0.1688(4) 0.0199(6) Uani 1 1 d . . . F26 F 0.66480(19) 0.59383(14) 0.1608(3) 0.0258(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0242(13) 0.0245(14) 0.0306(14) 0.0004(11) 0.0160(11) 0.0010(11) C12 0.0232(14) 0.0241(17) 0.0325(17) 0.0029(13) 0.0163(13) 0.0020(12) N13 0.0222(12) 0.0174(12) 0.0290(14) 0.0008(10) 0.0149(11) 0.0015(10) C14 0.0174(12) 0.0182(14) 0.0212(14) -0.0015(11) 0.0081(11) 0.0007(11) N15 0.0220(12) 0.0181(13) 0.0273(13) 0.0003(10) 0.0121(10) -0.0001(10) C16 0.0270(15) 0.0190(16) 0.0307(17) 0.0015(13) 0.0111(13) 0.0000(12) C17 0.0282(16) 0.0162(15) 0.0323(17) -0.0035(13) 0.0103(14) 0.0027(12) C18 0.0230(14) 0.0231(16) 0.0267(15) -0.0031(13) 0.0096(12) 0.0064(12) C19 0.0173(12) 0.0220(15) 0.0226(14) -0.0026(12) 0.0081(11) 0.0016(11) C21 0.0183(12) 0.0213(14) 0.0158(12) 0.0002(11) 0.0067(10) 0.0012(11) I1 0.01915(9) 0.02441(11) 0.02122(10) -0.00228(7) 0.00998(7) 0.00198(7) C22 0.0210(13) 0.0171(14) 0.0193(13) -0.0001(11) 0.0084(11) -0.0016(11) I2 0.02615(11) 0.02241(11) 0.03286(12) 0.00375(8) 0.01582(9) -0.00042(8) C23 0.0197(13) 0.0197(15) 0.0244(14) -0.0009(12) 0.0098(11) 0.0022(11) F23 0.0272(10) 0.0215(10) 0.0474(13) 0.0011(9) 0.0202(10) 0.0049(8) C24 0.0185(13) 0.0244(16) 0.0249(15) -0.0023(12) 0.0108(11) 0.0004(11) F24 0.0232(9) 0.0301(11) 0.0409(12) -0.0011(9) 0.0200(9) 0.0009(8) C25 0.0235(14) 0.0198(15) 0.0243(15) 0.0002(12) 0.0114(12) -0.0031(12) F25 0.0309(10) 0.0232(10) 0.0396(12) 0.0030(9) 0.0197(9) -0.0037(8) C26 0.0207(13) 0.0163(14) 0.0238(14) -0.0004(11) 0.0092(11) 0.0020(11) F26 0.0289(10) 0.0185(9) 0.0329(11) -0.0006(8) 0.0145(8) 0.0030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.314(4) . ? N11 C19 1.383(4) . ? C12 N13 1.362(4) . ? C12 H12 0.9500 . ? N13 C14 1.366(4) . ? N13 H13 0.8800 . ? C14 N15 1.334(4) . ? C14 C19 1.404(4) . ? N15 C16 1.338(4) . ? C16 C17 1.395(5) . ? C16 H16 0.9500 . ? C17 C18 1.381(5) . ? C17 H17 0.9500 . ? C18 C19 1.383(5) . ? C18 H18 0.9500 . ? C21 C26 1.376(4) . ? C21 C22 1.396(5) . ? C21 I1 2.101(3) . ? C22 C23 1.387(4) . ? C22 I2 2.085(3) . ? C23 F23 1.343(4) . ? C23 C24 1.378(5) . ? C24 F24 1.337(3) . ? C24 C25 1.367(5) . ? C25 F25 1.332(4) . ? C25 C26 1.379(4) . ? C26 F26 1.345(4) . ? 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 C12 N11 C19 105.0(3) . . ? N11 C12 N13 113.5(3) . . ? N11 C12 H12 123.3 . . ? N13 C12 H12 123.3 . . ? C12 N13 C14 106.2(3) . . ? C12 N13 H13 126.9 . . ? C14 N13 H13 126.9 . . ? N15 C14 N13 127.2(3) . . ? N15 C14 C19 126.5(3) . . ? N13 C14 C19 106.3(3) . . ? C14 N15 C16 113.9(3) . . ? N15 C16 C17 124.1(3) . . ? N15 C16 H16 118.0 . . ? C17 C16 H16 118.0 . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 116.3(3) . . ? C17 C18 H18 121.8 . . ? C19 C18 H18 121.8 . . ? N11 C19 C18 132.7(3) . . ? N11 C19 C14 109.0(3) . . ? C18 C19 C14 118.3(3) . . ? C26 C21 C22 118.4(3) . . ? C26 C21 I1 119.0(2) . . ? C22 C21 I1 122.6(2) . . ? C23 C22 C21 119.1(3) . . ? C23 C22 I2 117.7(2) . . ? C21 C22 I2 123.2(2) . . ? F23 C23 C24 117.3(3) . . ? F23 C23 C22 121.3(3) . . ? C24 C23 C22 121.3(3) . . ? F24 C24 C25 120.3(3) . . ? F24 C24 C23 120.0(3) . . ? C25 C24 C23 119.7(3) . . ? F25 C25 C24 119.9(3) . . ? F25 C25 C26 120.8(3) . . ? C24 C25 C26 119.3(3) . . ? F26 C26 C21 120.5(3) . . ? F26 C26 C25 117.3(3) . . ? C21 C26 C25 122.2(3) . . ? 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 C19 N11 C12 N13 -0.1(4) . . . . ? N11 C12 N13 C14 -0.1(4) . . . . ? C12 N13 C14 N15 -179.0(3) . . . . ? C12 N13 C14 C19 0.3(4) . . . . ? N13 C14 N15 C16 -180.0(3) . . . . ? C19 C14 N15 C16 0.9(5) . . . . ? C14 N15 C16 C17 0.4(5) . . . . ? N15 C16 C17 C18 -1.1(6) . . . . ? C16 C17 C18 C19 0.4(5) . . . . ? C12 N11 C19 C18 -179.2(4) . . . . ? C12 N11 C19 C14 0.3(4) . . . . ? C17 C18 C19 N11 -179.9(4) . . . . ? C17 C18 C19 C14 0.8(5) . . . . ? N15 C14 C19 N11 178.9(3) . . . . ? N13 C14 C19 N11 -0.3(4) . . . . ? N15 C14 C19 C18 -1.6(5) . . . . ? N13 C14 C19 C18 179.2(3) . . . . ? C26 C21 C22 C23 0.8(4) . . . . ? I1 C21 C22 C23 179.3(2) . . . . ? C26 C21 C22 I2 -176.7(2) . . . . ? I1 C21 C22 I2 1.9(4) . . . . ? C21 C22 C23 F23 179.6(3) . . . . ? I2 C22 C23 F23 -2.8(4) . . . . ? C21 C22 C23 C24 -2.0(5) . . . . ? I2 C22 C23 C24 175.5(3) . . . . ? F23 C23 C24 F24 0.8(5) . . . . ? C22 C23 C24 F24 -177.6(3) . . . . ? F23 C23 C24 C25 -179.9(3) . . . . ? C22 C23 C24 C25 1.6(5) . . . . ? F24 C24 C25 F25 -1.4(5) . . . . ? C23 C24 C25 F25 179.4(3) . . . . ? F24 C24 C25 C26 179.3(3) . . . . ? C23 C24 C25 C26 0.0(5) . . . . ? C22 C21 C26 F26 179.4(3) . . . . ? I1 C21 C26 F26 0.8(4) . . . . ? C22 C21 C26 C25 0.9(5) . . . . ? I1 C21 C26 C25 -177.7(2) . . . . ? F25 C25 C26 F26 0.8(5) . . . . ? C24 C25 C26 F26 -179.8(3) . . . . ? F25 C25 C26 C21 179.3(3) . . . . ? C24 C25 C26 C21 -1.3(5) . . . . ? 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 N13 H13 N15 0.88 1.97 2.843(4) 169.6 3_566 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.084 _refine_diff_density_min -1.579 _refine_diff_density_rms 0.176 _database_code_depnum_ccdc_archive 'CCDC 937215' ####################################################################### # # 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_ke1238m _audit_creation_method SHELXL-97 _chemical_name_systematic ; KEDPK24 3H-imidazo[4,5-b]pyridine, N-(2-methylphenyl)-N-(2-nitrophenyl)-urea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H5 N3) (C14 H13 N3 O3) ; _chemical_formula_sum 'C20 H18 N6 O3' _chemical_formula_weight 390.40 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7996(19) _cell_length_b 13.972(2) _cell_length_c 14.171(2) _cell_angle_alpha 119.480(10) _cell_angle_beta 104.641(11) _cell_angle_gamma 93.902(11) _cell_volume 1915.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3238 _cell_measurement_theta_min 3.80 _cell_measurement_theta_max 62.27 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8101 _exptl_absorpt_correction_T_max 0.8980 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23161 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0730 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 67.70 _reflns_number_total 6651 _reflns_number_gt 3947 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0030(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6651 _refine_ls_number_parameters 544 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.1978 _refine_ls_wR_factor_gt 0.1736 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11_1 N 1.1663(3) -0.0729(2) 0.4121(2) 0.0480(8) Uani 1 1 d . . . H11_1 H 1.227(3) -0.121(3) 0.415(3) 0.058 Uiso 1 1 d . . . C12_1 C 1.0536(3) -0.1089(3) 0.3351(3) 0.0507(9) Uani 1 1 d . . . H12_1 H 1.0211 -0.1852 0.2739 0.061 Uiso 1 1 calc R . . N13_1 N 0.9926(3) -0.0283(2) 0.3525(2) 0.0475(7) Uani 1 1 d . . . C14_1 C 1.0730(3) 0.0679(3) 0.4499(3) 0.0445(8) Uani 1 1 d . . . N15_1 N 1.0475(3) 0.1714(2) 0.5013(3) 0.0513(8) Uani 1 1 d . . . C16_1 C 1.1385(4) 0.2506(3) 0.5958(3) 0.0546(10) Uani 1 1 d . . . H16_1 H 1.1257 0.3247 0.6358 0.066 Uiso 1 1 calc R . . C17_1 C 1.2502(4) 0.2333(3) 0.6400(3) 0.0573(10) Uani 1 1 d . . . H17_1 H 1.3093 0.2947 0.7067 0.069 Uiso 1 1 calc R . . C18_1 C 1.2755(3) 0.1257(3) 0.5864(3) 0.0550(10) Uani 1 1 d . . . H18_1 H 1.3503 0.1109 0.6139 0.066 Uiso 1 1 calc R . . C19_1 C 1.1820(3) 0.0426(3) 0.4898(3) 0.0457(9) Uani 1 1 d . . . C21_1 C 0.7362(3) 0.0844(3) 0.2496(3) 0.0472(9) Uani 1 1 d . . . O21_1 O 0.6444(2) 0.09882(18) 0.1955(2) 0.0531(7) Uani 1 1 d . . . C31_1 C 0.6699(3) -0.1263(3) 0.1436(3) 0.0446(9) Uani 1 1 d . . . N31_1 N 0.7523(3) -0.0217(2) 0.2268(3) 0.0469(8) Uani 1 1 d . . . H31_1 H 0.831(3) -0.027(3) 0.261(3) 0.056 Uiso 1 1 d . . . C32_1 C 0.5477(3) -0.1390(3) 0.0881(3) 0.0497(9) Uani 1 1 d . . . H32_1 H 0.5148 -0.0744 0.1057 0.060 Uiso 1 1 calc R . . C33_1 C 0.4753(3) -0.2465(3) 0.0075(3) 0.0503(9) Uani 1 1 d . . . H33_1 H 0.3928 -0.2557 -0.0304 0.060 Uiso 1 1 calc R . . C34_1 C 0.5242(3) -0.3405(3) -0.0173(3) 0.0465(9) Uani 1 1 d . . . N34_1 N 0.4458(3) -0.4547(2) -0.1029(3) 0.0539(8) Uani 1 1 d . . . O34_1 O 0.3358(2) -0.4637(2) -0.1407(2) 0.0656(8) Uani 1 1 d . . . O35_1 O 0.4932(2) -0.53694(19) -0.1319(2) 0.0651(8) Uani 1 1 d . . . C35_1 C 0.6436(3) -0.3310(3) 0.0361(3) 0.0498(9) Uani 1 1 d . . . H35_1 H 0.6752 -0.3964 0.0176 0.060 Uiso 1 1 calc R . . C36_1 C 0.7167(3) -0.2236(3) 0.1177(3) 0.0479(9) Uani 1 1 d . . . H36_1 H 0.7986 -0.2157 0.1561 0.057 Uiso 1 1 calc R . . C41_1 C 0.8340(3) 0.2872(3) 0.3717(3) 0.0439(9) Uani 1 1 d . . . N41_1 N 0.8305(3) 0.1701(2) 0.3359(3) 0.0485(8) Uani 1 1 d . . . H41_1 H 0.890(3) 0.158(3) 0.393(3) 0.058 Uiso 1 1 d . . . C42_1 C 0.8420(3) 0.3265(3) 0.2991(3) 0.0471(9) Uani 1 1 d . . . C43_1 C 0.8514(3) 0.4435(3) 0.3445(3) 0.0485(9) Uani 1 1 d . . . H43_1 H 0.8562 0.4727 0.2973 0.058 Uiso 1 1 calc R . . C44_1 C 0.8538(3) 0.5172(3) 0.4565(3) 0.0496(9) Uani 1 1 d . . . H44_1 H 0.8604 0.5954 0.4846 0.060 Uiso 1 1 calc R . . C45_1 C 0.8465(3) 0.4763(3) 0.5269(3) 0.0481(9) Uani 1 1 d . . . H45_1 H 0.8498 0.5265 0.6038 0.058 Uiso 1 1 calc R . . C46_1 C 0.8344(3) 0.3603(3) 0.4836(3) 0.0481(9) Uani 1 1 d . . . H46_1 H 0.8264 0.3312 0.5303 0.058 Uiso 1 1 calc R . . C47_1 C 0.8458(3) 0.2489(3) 0.1788(3) 0.0552(10) Uani 1 1 d . . . H47A_1 H 0.9106 0.2093 0.1825 0.083 Uiso 1 1 calc R . . H47B_1 H 0.8606 0.2938 0.1456 0.083 Uiso 1 1 calc R . . H47C_1 H 0.7687 0.1937 0.1308 0.083 Uiso 1 1 calc R . . N11_2 N 0.4919(3) 0.7368(2) 0.7620(2) 0.0463(7) Uani 1 1 d . . . H11_2 H 0.438(3) 0.786(3) 0.765(3) 0.056 Uiso 1 1 d . . . C12_2 C 0.4562(3) 0.6231(3) 0.6824(3) 0.0482(9) Uani 1 1 d . . . H12_2 H 0.3763 0.5864 0.6310 0.058 Uiso 1 1 calc R . . N13_2 N 0.5459(3) 0.5689(2) 0.6844(2) 0.0492(8) Uani 1 1 d . . . C14_2 C 0.6453(3) 0.6546(3) 0.7685(3) 0.0439(8) Uani 1 1 d . . . N15_2 N 0.7580(3) 0.6393(2) 0.7990(3) 0.0500(8) Uani 1 1 d . . . C16_2 C 0.8406(3) 0.7354(3) 0.8831(3) 0.0554(10) Uani 1 1 d . . . H16_2 H 0.9213 0.7296 0.9066 0.067 Uiso 1 1 calc R . . C17_2 C 0.8162(3) 0.8436(3) 0.9385(3) 0.0521(9) Uani 1 1 d . . . H17_2 H 0.8791 0.9068 0.9977 0.063 Uiso 1 1 calc R . . C18_2 C 0.6998(3) 0.8578(3) 0.9066(3) 0.0491(9) Uani 1 1 d . . . H18_2 H 0.6804 0.9295 0.9426 0.059 Uiso 1 1 calc R . . C19_2 C 0.6132(3) 0.7602(3) 0.8184(3) 0.0446(8) Uani 1 1 d . . . C21_2 C 0.6494(3) 0.2976(3) 0.6141(3) 0.0470(9) Uani 1 1 d . . . O21_2 O 0.6614(2) 0.19862(19) 0.5795(2) 0.0568(7) Uani 1 1 d . . . C31_2 C 0.4507(3) 0.2451(3) 0.4681(3) 0.0448(9) Uani 1 1 d . . . N31_2 N 0.5519(3) 0.3232(2) 0.5612(3) 0.0474(8) Uani 1 1 d . . . H31_2 H 0.551(3) 0.399(3) 0.600(3) 0.057 Uiso 1 1 d . . . C32_2 C 0.4457(3) 0.1295(3) 0.3921(3) 0.0528(10) Uani 1 1 d . . . H32_2 H 0.5151 0.1003 0.4023 0.063 Uiso 1 1 calc R . . C33_2 C 0.3407(3) 0.0591(3) 0.3033(3) 0.0529(10) Uani 1 1 d . . . H33_2 H 0.3382 -0.0183 0.2534 0.063 Uiso 1 1 calc R . . C34_2 C 0.2391(3) 0.1011(3) 0.2867(3) 0.0465(9) Uani 1 1 d . . . N34_2 N 0.1283(3) 0.0264(2) 0.1927(3) 0.0544(8) Uani 1 1 d . . . O34_2 O 0.1318(2) -0.0715(2) 0.1212(2) 0.0690(8) Uani 1 1 d . . . O35_2 O 0.0358(2) 0.0634(2) 0.1854(2) 0.0603(7) Uani 1 1 d . . . C35_2 C 0.2419(3) 0.2155(3) 0.3593(3) 0.0487(9) Uani 1 1 d . . . H35_2 H 0.1721 0.2438 0.3477 0.058 Uiso 1 1 calc R . . C36_2 C 0.3463(3) 0.2865(3) 0.4476(3) 0.0469(9) Uani 1 1 d . . . H36_2 H 0.3484 0.3642 0.4954 0.056 Uiso 1 1 calc R . . C41_2 C 0.8374(3) 0.3800(3) 0.7789(3) 0.0453(9) Uani 1 1 d . . . N41_2 N 0.7333(2) 0.3897(2) 0.7070(3) 0.0472(8) Uani 1 1 d . . . H41_2 H 0.732(3) 0.465(3) 0.724(3) 0.057 Uiso 1 1 d . . . C42_2 C 0.8227(3) 0.3308(3) 0.8429(3) 0.0482(9) Uani 1 1 d . . . C43_2 C 0.9284(3) 0.3289(3) 0.9157(3) 0.0504(9) Uani 1 1 d . . . H43_2 H 0.9214 0.2948 0.9584 0.060 Uiso 1 1 calc R . . C44_2 C 1.0426(3) 0.3758(3) 0.9265(3) 0.0507(9) Uani 1 1 d . . . H44_2 H 1.1120 0.3747 0.9773 0.061 Uiso 1 1 calc R . . C45_2 C 1.0551(3) 0.4245(3) 0.8624(3) 0.0509(9) Uani 1 1 d . . . H45_2 H 1.1327 0.4560 0.8688 0.061 Uiso 1 1 calc R . . C46_2 C 0.9514(3) 0.4261(3) 0.7890(3) 0.0490(9) Uani 1 1 d . . . H46_2 H 0.9590 0.4590 0.7454 0.059 Uiso 1 1 calc R . . C47_2 C 0.7006(3) 0.2849(3) 0.8385(3) 0.0599(10) Uani 1 1 d . . . H47A_2 H 0.6508 0.3401 0.8471 0.090 Uiso 1 1 calc R . . H47B_2 H 0.7101 0.2707 0.9009 0.090 Uiso 1 1 calc R . . H47C_2 H 0.6618 0.2142 0.7646 0.090 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 N11_1 0.0491(18) 0.0351(15) 0.0508(18) 0.0178(14) 0.0119(15) 0.0151(13) C12_1 0.052(2) 0.0383(19) 0.053(2) 0.0192(18) 0.0133(18) 0.0119(16) N13_1 0.0512(18) 0.0392(16) 0.0475(17) 0.0201(14) 0.0135(15) 0.0172(14) C14_1 0.046(2) 0.0395(18) 0.046(2) 0.0216(17) 0.0121(17) 0.0129(15) N15_1 0.063(2) 0.0391(16) 0.0558(19) 0.0244(15) 0.0245(17) 0.0216(15) C16_1 0.066(3) 0.039(2) 0.055(2) 0.0213(18) 0.020(2) 0.0170(18) C17_1 0.069(3) 0.042(2) 0.051(2) 0.0204(18) 0.014(2) 0.0091(18) C18_1 0.052(2) 0.050(2) 0.054(2) 0.0236(19) 0.0109(18) 0.0075(17) C19_1 0.048(2) 0.0391(19) 0.046(2) 0.0207(17) 0.0123(17) 0.0127(16) C21_1 0.047(2) 0.0393(19) 0.050(2) 0.0192(17) 0.0146(18) 0.0154(16) O21_1 0.0482(15) 0.0382(13) 0.0593(16) 0.0201(12) 0.0074(12) 0.0155(11) C31_1 0.043(2) 0.0387(18) 0.049(2) 0.0215(17) 0.0123(17) 0.0117(15) N31_1 0.0409(17) 0.0364(15) 0.0525(18) 0.0201(14) 0.0053(14) 0.0111(13) C32_1 0.045(2) 0.0395(19) 0.055(2) 0.0208(18) 0.0113(18) 0.0108(16) C33_1 0.040(2) 0.051(2) 0.060(2) 0.0304(19) 0.0113(18) 0.0132(16) C34_1 0.045(2) 0.0349(18) 0.050(2) 0.0182(16) 0.0105(17) 0.0083(15) N34_1 0.0470(19) 0.0477(18) 0.056(2) 0.0253(16) 0.0064(16) 0.0071(15) O34_1 0.0481(16) 0.0545(16) 0.0729(19) 0.0284(15) 0.0005(14) 0.0046(13) O35_1 0.0642(18) 0.0363(14) 0.0745(19) 0.0202(13) 0.0110(15) 0.0135(13) C35_1 0.051(2) 0.0379(19) 0.054(2) 0.0229(17) 0.0104(18) 0.0124(16) C36_1 0.041(2) 0.0425(19) 0.048(2) 0.0197(17) 0.0045(16) 0.0124(15) C41_1 0.0417(19) 0.0358(18) 0.048(2) 0.0183(16) 0.0127(16) 0.0122(15) N41_1 0.0508(19) 0.0369(16) 0.0501(18) 0.0203(14) 0.0092(15) 0.0139(13) C42_1 0.042(2) 0.0425(19) 0.049(2) 0.0199(17) 0.0128(17) 0.0124(15) C43_1 0.044(2) 0.048(2) 0.059(2) 0.0310(19) 0.0168(18) 0.0154(16) C44_1 0.047(2) 0.0387(19) 0.054(2) 0.0192(18) 0.0131(18) 0.0131(16) C45_1 0.047(2) 0.0402(19) 0.045(2) 0.0156(17) 0.0100(17) 0.0111(16) C46_1 0.049(2) 0.0420(19) 0.049(2) 0.0216(17) 0.0128(17) 0.0117(16) C47_1 0.068(3) 0.052(2) 0.056(2) 0.0302(19) 0.029(2) 0.0269(19) N11_2 0.0427(17) 0.0347(15) 0.0520(18) 0.0188(14) 0.0091(14) 0.0108(13) C12_2 0.046(2) 0.0391(19) 0.053(2) 0.0234(17) 0.0078(17) 0.0103(16) N13_2 0.0436(17) 0.0389(16) 0.0573(19) 0.0227(15) 0.0096(15) 0.0130(13) C14_2 0.042(2) 0.0418(19) 0.045(2) 0.0214(16) 0.0129(16) 0.0146(15) N15_2 0.0426(17) 0.0498(17) 0.0539(18) 0.0267(15) 0.0107(15) 0.0136(14) C16_2 0.042(2) 0.064(2) 0.057(2) 0.031(2) 0.0111(19) 0.0109(18) C17_2 0.053(2) 0.046(2) 0.047(2) 0.0220(18) 0.0083(18) 0.0066(17) C18_2 0.053(2) 0.0386(19) 0.048(2) 0.0198(17) 0.0112(18) 0.0103(16) C19_2 0.043(2) 0.0401(18) 0.049(2) 0.0229(16) 0.0130(17) 0.0112(15) C21_2 0.043(2) 0.0404(19) 0.053(2) 0.0222(17) 0.0124(17) 0.0159(16) O21_2 0.0525(16) 0.0382(13) 0.0622(17) 0.0184(12) 0.0079(13) 0.0162(11) C31_2 0.045(2) 0.0375(18) 0.045(2) 0.0183(16) 0.0109(16) 0.0103(15) N31_2 0.0462(17) 0.0334(15) 0.0507(18) 0.0173(14) 0.0072(14) 0.0136(13) C32_2 0.052(2) 0.042(2) 0.052(2) 0.0170(18) 0.0131(18) 0.0180(17) C33_2 0.055(2) 0.0384(19) 0.053(2) 0.0197(17) 0.0078(19) 0.0125(17) C34_2 0.043(2) 0.0390(19) 0.046(2) 0.0191(17) 0.0066(16) 0.0059(15) N34_2 0.056(2) 0.0443(18) 0.057(2) 0.0260(16) 0.0111(16) 0.0080(15) O34_2 0.0726(19) 0.0375(14) 0.0649(18) 0.0136(13) 0.0040(15) 0.0079(13) O35_2 0.0472(16) 0.0540(16) 0.0636(18) 0.0259(14) 0.0052(13) 0.0093(12) C35_2 0.049(2) 0.042(2) 0.050(2) 0.0212(18) 0.0131(18) 0.0153(16) C36_2 0.049(2) 0.0370(18) 0.047(2) 0.0180(16) 0.0124(17) 0.0131(15) C41_2 0.044(2) 0.0388(19) 0.044(2) 0.0172(17) 0.0099(16) 0.0152(16) N41_2 0.0405(17) 0.0374(15) 0.0519(18) 0.0189(14) 0.0062(14) 0.0140(13) C42_2 0.050(2) 0.0390(19) 0.047(2) 0.0168(17) 0.0143(18) 0.0157(16) C43_2 0.058(2) 0.0369(19) 0.048(2) 0.0178(17) 0.0136(19) 0.0183(17) C44_2 0.053(2) 0.0419(19) 0.044(2) 0.0157(17) 0.0083(18) 0.0172(17) C45_2 0.047(2) 0.045(2) 0.047(2) 0.0172(18) 0.0110(18) 0.0119(16) C46_2 0.049(2) 0.0404(19) 0.047(2) 0.0164(17) 0.0134(17) 0.0134(16) C47_2 0.059(3) 0.058(2) 0.065(3) 0.034(2) 0.022(2) 0.0147(19) _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 N11_1 C12_1 1.359(4) . ? N11_1 C19_1 1.399(4) . ? N11_1 H11_1 1.02(3) . ? C12_1 N13_1 1.332(4) . ? C12_1 H12_1 0.9500 . ? N13_1 C14_1 1.397(4) . ? C14_1 N15_1 1.359(4) . ? C14_1 C19_1 1.411(4) . ? N15_1 C16_1 1.350(5) . ? C16_1 C17_1 1.402(5) . ? C16_1 H16_1 0.9500 . ? C17_1 C18_1 1.406(5) . ? C17_1 H17_1 0.9500 . ? C18_1 C19_1 1.391(5) . ? C18_1 H18_1 0.9500 . ? C21_1 O21_1 1.251(4) . ? C21_1 N41_1 1.362(4) . ? C21_1 N31_1 1.391(4) . ? C31_1 C32_1 1.408(5) . ? C31_1 C36_1 1.414(4) . ? C31_1 N31_1 1.415(4) . ? N31_1 H31_1 0.96(3) . ? C32_1 C33_1 1.391(5) . ? C32_1 H32_1 0.9500 . ? C33_1 C34_1 1.390(4) . ? C33_1 H33_1 0.9500 . ? C34_1 C35_1 1.383(5) . ? C34_1 N34_1 1.483(4) . ? N34_1 O35_1 1.241(3) . ? N34_1 O34_1 1.245(4) . ? C35_1 C36_1 1.395(5) . ? C35_1 H35_1 0.9500 . ? C36_1 H36_1 0.9500 . ? C41_1 C46_1 1.399(4) . ? C41_1 C42_1 1.401(5) . ? C41_1 N41_1 1.450(4) . ? N41_1 H41_1 1.02(4) . ? C42_1 C43_1 1.415(5) . ? C42_1 C47_1 1.520(5) . ? C43_1 C44_1 1.395(5) . ? C43_1 H43_1 0.9500 . ? C44_1 C45_1 1.388(5) . ? C44_1 H44_1 0.9500 . ? C45_1 C46_1 1.404(5) . ? C45_1 H45_1 0.9500 . ? C46_1 H46_1 0.9500 . ? C47_1 H47A_1 0.9800 . ? C47_1 H47B_1 0.9800 . ? C47_1 H47C_1 0.9800 . ? N11_2 C12_2 1.370(4) . ? N11_2 C19_2 1.377(4) . ? N11_2 H11_2 0.97(3) . ? C12_2 N13_2 1.346(4) . ? C12_2 H12_2 0.9500 . ? N13_2 C14_2 1.388(4) . ? C14_2 N15_2 1.355(4) . ? C14_2 C19_2 1.416(4) . ? N15_2 C16_2 1.354(4) . ? C16_2 C17_2 1.410(5) . ? C16_2 H16_2 0.9500 . ? C17_2 C18_2 1.394(5) . ? C17_2 H17_2 0.9500 . ? C18_2 C19_2 1.397(5) . ? C18_2 H18_2 0.9500 . ? C21_2 O21_2 1.252(4) . ? C21_2 N41_2 1.368(4) . ? C21_2 N31_2 1.378(4) . ? C31_2 N31_2 1.402(4) . ? C31_2 C32_2 1.420(4) . ? C31_2 C36_2 1.420(4) . ? N31_2 H31_2 0.93(3) . ? C32_2 C33_2 1.383(5) . ? C32_2 H32_2 0.9500 . ? C33_2 C34_2 1.388(5) . ? C33_2 H33_2 0.9500 . ? C34_2 C35_2 1.404(4) . ? C34_2 N34_2 1.462(4) . ? N34_2 O35_2 1.241(3) . ? N34_2 O34_2 1.250(3) . ? C35_2 C36_2 1.378(5) . ? C35_2 H35_2 0.9500 . ? C36_2 H36_2 0.9500 . ? C41_2 C46_2 1.392(5) . ? C41_2 C42_2 1.416(5) . ? C41_2 N41_2 1.446(4) . ? N41_2 H41_2 0.96(3) . ? C42_2 C43_2 1.415(5) . ? C42_2 C47_2 1.510(5) . ? C43_2 C44_2 1.394(5) . ? C43_2 H43_2 0.9500 . ? C44_2 C45_2 1.405(5) . ? C44_2 H44_2 0.9500 . ? C45_2 C46_2 1.401(5) . ? C45_2 H45_2 0.9500 . ? C46_2 H46_2 0.9500 . ? C47_2 H47A_2 0.9800 . ? C47_2 H47B_2 0.9800 . ? C47_2 H47C_2 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 C12_1 N11_1 C19_1 106.7(3) . . ? C12_1 N11_1 H11_1 127.3(19) . . ? C19_1 N11_1 H11_1 125.9(19) . . ? N13_1 C12_1 N11_1 114.5(3) . . ? N13_1 C12_1 H12_1 122.8 . . ? N11_1 C12_1 H12_1 122.8 . . ? C12_1 N13_1 C14_1 103.3(3) . . ? N15_1 C14_1 N13_1 124.1(3) . . ? N15_1 C14_1 C19_1 124.7(3) . . ? N13_1 C14_1 C19_1 111.2(3) . . ? C16_1 N15_1 C14_1 113.2(3) . . ? N15_1 C16_1 C17_1 125.8(3) . . ? N15_1 C16_1 H16_1 117.1 . . ? C17_1 C16_1 H16_1 117.1 . . ? C16_1 C17_1 C18_1 120.5(4) . . ? C16_1 C17_1 H17_1 119.8 . . ? C18_1 C17_1 H17_1 119.8 . . ? C19_1 C18_1 C17_1 114.5(4) . . ? C19_1 C18_1 H18_1 122.8 . . ? C17_1 C18_1 H18_1 122.8 . . ? C18_1 C19_1 N11_1 134.4(3) . . ? C18_1 C19_1 C14_1 121.3(3) . . ? N11_1 C19_1 C14_1 104.3(3) . . ? O21_1 C21_1 N41_1 123.8(3) . . ? O21_1 C21_1 N31_1 123.0(3) . . ? N41_1 C21_1 N31_1 113.2(3) . . ? C32_1 C31_1 C36_1 119.3(3) . . ? C32_1 C31_1 N31_1 124.9(3) . . ? C36_1 C31_1 N31_1 115.7(3) . . ? C21_1 N31_1 C31_1 126.4(3) . . ? C21_1 N31_1 H31_1 117(2) . . ? C31_1 N31_1 H31_1 115(2) . . ? C33_1 C32_1 C31_1 119.8(3) . . ? C33_1 C32_1 H32_1 120.1 . . ? C31_1 C32_1 H32_1 120.1 . . ? C34_1 C33_1 C32_1 119.6(3) . . ? C34_1 C33_1 H33_1 120.2 . . ? C32_1 C33_1 H33_1 120.2 . . ? C35_1 C34_1 C33_1 122.1(3) . . ? C35_1 C34_1 N34_1 118.8(3) . . ? C33_1 C34_1 N34_1 119.1(3) . . ? O35_1 N34_1 O34_1 123.2(3) . . ? O35_1 N34_1 C34_1 118.2(3) . . ? O34_1 N34_1 C34_1 118.6(3) . . ? C34_1 C35_1 C36_1 118.7(3) . . ? C34_1 C35_1 H35_1 120.6 . . ? C36_1 C35_1 H35_1 120.6 . . ? C35_1 C36_1 C31_1 120.5(3) . . ? C35_1 C36_1 H36_1 119.7 . . ? C31_1 C36_1 H36_1 119.7 . . ? C46_1 C41_1 C42_1 121.5(3) . . ? C46_1 C41_1 N41_1 117.0(3) . . ? C42_1 C41_1 N41_1 121.4(3) . . ? C21_1 N41_1 C41_1 122.4(3) . . ? C21_1 N41_1 H41_1 120(2) . . ? C41_1 N41_1 H41_1 115.0(19) . . ? C41_1 C42_1 C43_1 116.9(3) . . ? C41_1 C42_1 C47_1 122.1(3) . . ? C43_1 C42_1 C47_1 120.9(3) . . ? C44_1 C43_1 C42_1 122.0(4) . . ? C44_1 C43_1 H43_1 119.0 . . ? C42_1 C43_1 H43_1 119.0 . . ? C45_1 C44_1 C43_1 120.0(3) . . ? C45_1 C44_1 H44_1 120.0 . . ? C43_1 C44_1 H44_1 120.0 . . ? C44_1 C45_1 C46_1 119.4(3) . . ? C44_1 C45_1 H45_1 120.3 . . ? C46_1 C45_1 H45_1 120.3 . . ? C41_1 C46_1 C45_1 120.2(4) . . ? C41_1 C46_1 H46_1 119.9 . . ? C45_1 C46_1 H46_1 119.9 . . ? C42_1 C47_1 H47A_1 109.5 . . ? C42_1 C47_1 H47B_1 109.5 . . ? H47A_1 C47_1 H47B_1 109.5 . . ? C42_1 C47_1 H47C_1 109.5 . . ? H47A_1 C47_1 H47C_1 109.5 . . ? H47B_1 C47_1 H47C_1 109.5 . . ? C12_2 N11_2 C19_2 107.3(3) . . ? C12_2 N11_2 H11_2 121(2) . . ? C19_2 N11_2 H11_2 131(2) . . ? N13_2 C12_2 N11_2 113.1(3) . . ? N13_2 C12_2 H12_2 123.4 . . ? N11_2 C12_2 H12_2 123.4 . . ? C12_2 N13_2 C14_2 103.7(3) . . ? N15_2 C14_2 N13_2 124.6(3) . . ? N15_2 C14_2 C19_2 124.5(3) . . ? N13_2 C14_2 C19_2 110.9(3) . . ? C16_2 N15_2 C14_2 114.1(3) . . ? N15_2 C16_2 C17_2 125.1(3) . . ? N15_2 C16_2 H16_2 117.4 . . ? C17_2 C16_2 H16_2 117.4 . . ? C18_2 C17_2 C16_2 120.1(3) . . ? C18_2 C17_2 H17_2 120.0 . . ? C16_2 C17_2 H17_2 120.0 . . ? C17_2 C18_2 C19_2 115.9(3) . . ? C17_2 C18_2 H18_2 122.0 . . ? C19_2 C18_2 H18_2 122.0 . . ? N11_2 C19_2 C18_2 134.8(3) . . ? N11_2 C19_2 C14_2 105.0(3) . . ? C18_2 C19_2 C14_2 120.3(3) . . ? O21_2 C21_2 N41_2 122.6(3) . . ? O21_2 C21_2 N31_2 123.1(3) . . ? N41_2 C21_2 N31_2 114.3(3) . . ? N31_2 C31_2 C32_2 125.1(3) . . ? N31_2 C31_2 C36_2 116.9(3) . . ? C32_2 C31_2 C36_2 118.0(3) . . ? C21_2 N31_2 C31_2 126.0(3) . . ? C21_2 N31_2 H31_2 114(2) . . ? C31_2 N31_2 H31_2 119(2) . . ? C33_2 C32_2 C31_2 120.6(3) . . ? C33_2 C32_2 H32_2 119.7 . . ? C31_2 C32_2 H32_2 119.7 . . ? C32_2 C33_2 C34_2 120.3(3) . . ? C32_2 C33_2 H33_2 119.9 . . ? C34_2 C33_2 H33_2 119.9 . . ? C33_2 C34_2 C35_2 120.4(3) . . ? C33_2 C34_2 N34_2 120.1(3) . . ? C35_2 C34_2 N34_2 119.5(3) . . ? O35_2 N34_2 O34_2 122.8(3) . . ? O35_2 N34_2 C34_2 118.9(3) . . ? O34_2 N34_2 C34_2 118.3(3) . . ? C36_2 C35_2 C34_2 119.8(3) . . ? C36_2 C35_2 H35_2 120.1 . . ? C34_2 C35_2 H35_2 120.1 . . ? C35_2 C36_2 C31_2 120.9(3) . . ? C35_2 C36_2 H36_2 119.5 . . ? C31_2 C36_2 H36_2 119.5 . . ? C46_2 C41_2 C42_2 121.0(3) . . ? C46_2 C41_2 N41_2 118.7(3) . . ? C42_2 C41_2 N41_2 120.1(3) . . ? C21_2 N41_2 C41_2 122.5(3) . . ? C21_2 N41_2 H41_2 122(2) . . ? C41_2 N41_2 H41_2 115(2) . . ? C43_2 C42_2 C41_2 117.3(3) . . ? C43_2 C42_2 C47_2 120.1(4) . . ? C41_2 C42_2 C47_2 122.6(3) . . ? C44_2 C43_2 C42_2 121.7(4) . . ? C44_2 C43_2 H43_2 119.1 . . ? C42_2 C43_2 H43_2 119.1 . . ? C43_2 C44_2 C45_2 120.1(4) . . ? C43_2 C44_2 H44_2 119.9 . . ? C45_2 C44_2 H44_2 119.9 . . ? C46_2 C45_2 C44_2 118.9(4) . . ? C46_2 C45_2 H45_2 120.5 . . ? C44_2 C45_2 H45_2 120.5 . . ? C41_2 C46_2 C45_2 120.9(4) . . ? C41_2 C46_2 H46_2 119.5 . . ? C45_2 C46_2 H46_2 119.5 . . ? C42_2 C47_2 H47A_2 109.5 . . ? C42_2 C47_2 H47B_2 109.5 . . ? H47A_2 C47_2 H47B_2 109.5 . . ? C42_2 C47_2 H47C_2 109.5 . . ? H47A_2 C47_2 H47C_2 109.5 . . ? H47B_2 C47_2 H47C_2 109.5 . . ? 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 C19_1 N11_1 C12_1 N13_1 0.9(4) . . . . ? N11_1 C12_1 N13_1 C14_1 -0.4(4) . . . . ? C12_1 N13_1 C14_1 N15_1 -178.3(3) . . . . ? C12_1 N13_1 C14_1 C19_1 -0.3(4) . . . . ? N13_1 C14_1 N15_1 C16_1 178.5(3) . . . . ? C19_1 C14_1 N15_1 C16_1 0.7(5) . . . . ? C14_1 N15_1 C16_1 C17_1 0.6(6) . . . . ? N15_1 C16_1 C17_1 C18_1 -0.8(6) . . . . ? C16_1 C17_1 C18_1 C19_1 -0.2(5) . . . . ? C17_1 C18_1 C19_1 N11_1 -179.4(4) . . . . ? C17_1 C18_1 C19_1 C14_1 1.3(5) . . . . ? C12_1 N11_1 C19_1 C18_1 179.7(4) . . . . ? C12_1 N11_1 C19_1 C14_1 -1.0(4) . . . . ? N15_1 C14_1 C19_1 C18_1 -1.7(6) . . . . ? N13_1 C14_1 C19_1 C18_1 -179.8(3) . . . . ? N15_1 C14_1 C19_1 N11_1 178.8(3) . . . . ? N13_1 C14_1 C19_1 N11_1 0.8(4) . . . . ? O21_1 C21_1 N31_1 C31_1 -1.3(6) . . . . ? N41_1 C21_1 N31_1 C31_1 179.1(3) . . . . ? C32_1 C31_1 N31_1 C21_1 -15.2(6) . . . . ? C36_1 C31_1 N31_1 C21_1 165.8(3) . . . . ? C36_1 C31_1 C32_1 C33_1 -1.1(5) . . . . ? N31_1 C31_1 C32_1 C33_1 180.0(3) . . . . ? C31_1 C32_1 C33_1 C34_1 0.2(6) . . . . ? C32_1 C33_1 C34_1 C35_1 0.2(6) . . . . ? C32_1 C33_1 C34_1 N34_1 179.6(3) . . . . ? C35_1 C34_1 N34_1 O35_1 -7.2(5) . . . . ? C33_1 C34_1 N34_1 O35_1 173.4(3) . . . . ? C35_1 C34_1 N34_1 O34_1 171.7(3) . . . . ? C33_1 C34_1 N34_1 O34_1 -7.8(5) . . . . ? C33_1 C34_1 C35_1 C36_1 0.3(6) . . . . ? N34_1 C34_1 C35_1 C36_1 -179.2(3) . . . . ? C34_1 C35_1 C36_1 C31_1 -1.1(6) . . . . ? C32_1 C31_1 C36_1 C35_1 1.5(5) . . . . ? N31_1 C31_1 C36_1 C35_1 -179.4(3) . . . . ? O21_1 C21_1 N41_1 C41_1 -1.3(6) . . . . ? N31_1 C21_1 N41_1 C41_1 178.3(3) . . . . ? C46_1 C41_1 N41_1 C21_1 115.9(4) . . . . ? C42_1 C41_1 N41_1 C21_1 -66.8(5) . . . . ? C46_1 C41_1 C42_1 C43_1 0.4(5) . . . . ? N41_1 C41_1 C42_1 C43_1 -176.7(3) . . . . ? C46_1 C41_1 C42_1 C47_1 178.0(3) . . . . ? N41_1 C41_1 C42_1 C47_1 0.8(5) . . . . ? C41_1 C42_1 C43_1 C44_1 0.6(5) . . . . ? C47_1 C42_1 C43_1 C44_1 -177.0(3) . . . . ? C42_1 C43_1 C44_1 C45_1 -0.2(5) . . . . ? C43_1 C44_1 C45_1 C46_1 -1.3(5) . . . . ? C42_1 C41_1 C46_1 C45_1 -1.9(5) . . . . ? N41_1 C41_1 C46_1 C45_1 175.3(3) . . . . ? C44_1 C45_1 C46_1 C41_1 2.3(5) . . . . ? C19_2 N11_2 C12_2 N13_2 1.6(4) . . . . ? N11_2 C12_2 N13_2 C14_2 -1.8(4) . . . . ? C12_2 N13_2 C14_2 N15_2 -178.8(3) . . . . ? C12_2 N13_2 C14_2 C19_2 1.4(4) . . . . ? N13_2 C14_2 N15_2 C16_2 179.9(3) . . . . ? C19_2 C14_2 N15_2 C16_2 -0.2(5) . . . . ? C14_2 N15_2 C16_2 C17_2 1.2(5) . . . . ? N15_2 C16_2 C17_2 C18_2 -0.9(6) . . . . ? C16_2 C17_2 C18_2 C19_2 -0.3(5) . . . . ? C12_2 N11_2 C19_2 C18_2 -179.9(4) . . . . ? C12_2 N11_2 C19_2 C14_2 -0.6(4) . . . . ? C17_2 C18_2 C19_2 N11_2 -179.6(4) . . . . ? C17_2 C18_2 C19_2 C14_2 1.2(5) . . . . ? N15_2 C14_2 C19_2 N11_2 179.6(3) . . . . ? N13_2 C14_2 C19_2 N11_2 -0.5(4) . . . . ? N15_2 C14_2 C19_2 C18_2 -1.0(6) . . . . ? N13_2 C14_2 C19_2 C18_2 178.9(3) . . . . ? O21_2 C21_2 N31_2 C31_2 4.2(6) . . . . ? N41_2 C21_2 N31_2 C31_2 -176.7(3) . . . . ? C32_2 C31_2 N31_2 C21_2 -19.3(6) . . . . ? C36_2 C31_2 N31_2 C21_2 162.2(3) . . . . ? N31_2 C31_2 C32_2 C33_2 179.4(4) . . . . ? C36_2 C31_2 C32_2 C33_2 -2.2(5) . . . . ? C31_2 C32_2 C33_2 C34_2 0.7(6) . . . . ? C32_2 C33_2 C34_2 C35_2 0.4(6) . . . . ? C32_2 C33_2 C34_2 N34_2 180.0(3) . . . . ? C33_2 C34_2 N34_2 O35_2 174.0(3) . . . . ? C35_2 C34_2 N34_2 O35_2 -6.5(5) . . . . ? C33_2 C34_2 N34_2 O34_2 -7.8(5) . . . . ? C35_2 C34_2 N34_2 O34_2 171.7(3) . . . . ? C33_2 C34_2 C35_2 C36_2 0.0(6) . . . . ? N34_2 C34_2 C35_2 C36_2 -179.6(3) . . . . ? C34_2 C35_2 C36_2 C31_2 -1.5(6) . . . . ? N31_2 C31_2 C36_2 C35_2 -178.8(3) . . . . ? C32_2 C31_2 C36_2 C35_2 2.6(5) . . . . ? O21_2 C21_2 N41_2 C41_2 -5.5(6) . . . . ? N31_2 C21_2 N41_2 C41_2 175.3(3) . . . . ? C46_2 C41_2 N41_2 C21_2 120.0(4) . . . . ? C42_2 C41_2 N41_2 C21_2 -63.9(4) . . . . ? C46_2 C41_2 C42_2 C43_2 -1.0(5) . . . . ? N41_2 C41_2 C42_2 C43_2 -177.0(3) . . . . ? C46_2 C41_2 C42_2 C47_2 177.1(3) . . . . ? N41_2 C41_2 C42_2 C47_2 1.1(5) . . . . ? C41_2 C42_2 C43_2 C44_2 1.5(5) . . . . ? C47_2 C42_2 C43_2 C44_2 -176.6(3) . . . . ? C42_2 C43_2 C44_2 C45_2 -1.3(5) . . . . ? C43_2 C44_2 C45_2 C46_2 0.6(5) . . . . ? C42_2 C41_2 C46_2 C45_2 0.4(5) . . . . ? N41_2 C41_2 C46_2 C45_2 176.4(3) . . . . ? C44_2 C45_2 C46_2 C41_2 -0.2(5) . . . . ? 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 N11_1 H11_1 O21_2 1.02(3) 1.77(4) 2.794(4) 177(3) 2_756 N11_2 H11_2 O21_1 0.97(3) 1.85(3) 2.803(3) 167(3) 2_666 N31_1 H31_1 N13_1 0.96(3) 2.02(4) 2.978(4) 172(3) . N31_2 H31_2 N13_2 0.93(3) 2.08(3) 3.005(4) 179(4) . N41_1 H41_1 N15_1 1.02(4) 2.02(4) 2.994(4) 160(3) . N41_2 H41_2 N15_2 0.96(3) 2.08(3) 3.024(4) 166(3) . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 67.70 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.461 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.119 _database_code_depnum_ccdc_archive 'CCDC 937216' ####################################################################### # # 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_ke1305m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 N6 O' _chemical_formula_weight 356.39 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.547(4) _cell_length_b 9.842(4) _cell_length_c 10.684(5) _cell_angle_alpha 76.349(9) _cell_angle_beta 89.136(10) _cell_angle_gamma 79.581(10) _cell_volume 858.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9768 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 2891 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 24.68 _reflns_number_total 2237 _reflns_number_gt 1589 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 2237 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.2270 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 1.496 _refine_ls_restrained_S_all 1.496 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.2815(4) 0.0613(4) 0.5403(3) 0.0369(9) Uani 1 1 d . . . H11 H 0.266(5) -0.030(5) 0.558(4) 0.044 Uiso 1 1 d . . . C12 C 0.2083(5) 0.1899(5) 0.4733(4) 0.0377(11) Uani 1 1 d . . . H12 H 0.1260 0.2025 0.4106 0.045 Uiso 1 1 calc R . . N13 N 0.2612(4) 0.2978(4) 0.5026(3) 0.0365(9) Uani 1 1 d . . . C14 C 0.3802(5) 0.2309(4) 0.5960(4) 0.0294(10) Uani 1 1 d . . . N15 N 0.4670(4) 0.2980(4) 0.6541(3) 0.0353(9) Uani 1 1 d . . . C16 C 0.5742(5) 0.2115(5) 0.7429(4) 0.0398(11) Uani 1 1 d . . . H16 H 0.6383 0.2540 0.7887 0.048 Uiso 1 1 calc R . . C17 C 0.5961(6) 0.0644(5) 0.7708(4) 0.0445(12) Uani 1 1 d . . . H17 H 0.6749 0.0099 0.8334 0.053 Uiso 1 1 calc R . . C18 C 0.5049(5) -0.0046(5) 0.7090(4) 0.0408(11) Uani 1 1 d . . . H18 H 0.5187 -0.1053 0.7262 0.049 Uiso 1 1 calc R . . C19 C 0.3927(5) 0.0840(5) 0.6206(4) 0.0322(10) Uani 1 1 d . . . C21 C 0.2196(5) 0.6790(4) 0.5439(4) 0.0327(10) Uani 1 1 d . . . O21 O 0.1843(3) 0.8074(3) 0.5408(3) 0.0389(8) Uani 1 1 d . . . C31 C 0.3814(5) 0.6273(4) 0.7443(4) 0.0326(10) Uani 1 1 d . . . N31 N 0.3168(4) 0.5873(4) 0.6414(3) 0.0330(9) Uani 1 1 d . . . H31 H 0.360(5) 0.503(5) 0.622(4) 0.040 Uiso 1 1 d . . . C32 C 0.2888(5) 0.6954(4) 0.8278(4) 0.0315(10) Uani 1 1 d . . . C33 C 0.3548(5) 0.7292(4) 0.9314(4) 0.0364(10) Uani 1 1 d . . . H33 H 0.2897 0.7790 0.9850 0.044 Uiso 1 1 calc R . . C34 C 0.5192(5) 0.6886(5) 0.9559(4) 0.0385(11) Uani 1 1 d . . . H34 H 0.5669 0.7088 1.0276 0.046 Uiso 1 1 calc R . . C35 C 0.6114(5) 0.6189(5) 0.8747(4) 0.0376(11) Uani 1 1 d . . . H35 H 0.7228 0.5905 0.8916 0.045 Uiso 1 1 calc R . . C36 C 0.5444(5) 0.5897(4) 0.7691(4) 0.0332(10) Uani 1 1 d . . . H36 H 0.6104 0.5437 0.7133 0.040 Uiso 1 1 calc R . . C37 C 0.1166(5) 0.7269(4) 0.8108(4) 0.0340(10) Uani 1 1 d . . . N37 N -0.0194(5) 0.7486(4) 0.8072(4) 0.0464(10) Uani 1 1 d . . . C41 C 0.0773(5) 0.6800(4) 0.3428(4) 0.0302(10) Uani 1 1 d . . . N41 N 0.1652(4) 0.6153(4) 0.4591(3) 0.0321(9) Uani 1 1 d . . . H41 H 0.176(6) 0.537(5) 0.464(4) 0.038 Uiso 1 1 d . . . C42 C 0.0336(5) 0.8266(4) 0.2931(4) 0.0351(11) Uani 1 1 d . . . H42 H 0.0611 0.8905 0.3397 0.042 Uiso 1 1 calc R . . C43 C -0.0479(5) 0.8786(5) 0.1782(4) 0.0374(11) Uani 1 1 d . . . H43 H -0.0750 0.9785 0.1447 0.045 Uiso 1 1 calc R . . C44 C -0.0919(5) 0.7873(5) 0.1095(4) 0.0444(12) Uani 1 1 d . . . H44 H -0.1505 0.8243 0.0302 0.053 Uiso 1 1 calc R . . C45 C -0.0497(5) 0.6426(5) 0.1576(4) 0.0437(12) Uani 1 1 d . . . H45 H -0.0787 0.5794 0.1110 0.052 Uiso 1 1 calc R . . C46 C 0.0335(5) 0.5898(5) 0.2718(4) 0.0373(11) Uani 1 1 d . . . H46 H 0.0623 0.4898 0.3037 0.045 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 N11 0.036(2) 0.031(2) 0.044(2) -0.0052(18) 0.0036(17) -0.0114(18) C12 0.031(2) 0.039(3) 0.041(3) -0.005(2) 0.0016(19) -0.007(2) N13 0.029(2) 0.040(2) 0.047(2) -0.0144(18) 0.0014(17) -0.0168(17) C14 0.025(2) 0.035(2) 0.031(2) -0.0079(19) 0.0077(18) -0.0094(19) N15 0.030(2) 0.039(2) 0.042(2) -0.0130(17) 0.0051(17) -0.0136(17) C16 0.031(2) 0.051(3) 0.041(3) -0.011(2) 0.002(2) -0.015(2) C17 0.040(3) 0.046(3) 0.044(3) -0.004(2) 0.003(2) -0.009(2) C18 0.037(3) 0.035(3) 0.050(3) -0.005(2) 0.006(2) -0.010(2) C19 0.027(2) 0.041(3) 0.033(2) -0.013(2) 0.0075(19) -0.014(2) C21 0.029(2) 0.033(3) 0.037(2) -0.005(2) 0.0077(19) -0.013(2) O21 0.0341(17) 0.0339(18) 0.0521(19) -0.0121(14) 0.0029(14) -0.0127(14) C31 0.036(2) 0.026(2) 0.033(2) 0.0027(18) 0.0032(19) -0.0099(19) N31 0.030(2) 0.037(2) 0.036(2) -0.0111(17) -0.0016(16) -0.0112(16) C32 0.032(2) 0.028(2) 0.032(2) -0.0003(19) 0.0019(19) -0.0074(19) C33 0.036(2) 0.039(2) 0.036(2) -0.008(2) 0.000(2) -0.011(2) C34 0.032(2) 0.044(3) 0.042(3) -0.007(2) 0.000(2) -0.015(2) C35 0.027(2) 0.041(3) 0.043(3) -0.003(2) -0.002(2) -0.012(2) C36 0.030(2) 0.030(2) 0.036(2) 0.0005(19) 0.0017(19) -0.0087(19) C37 0.033(3) 0.040(3) 0.032(2) -0.010(2) 0.0021(19) -0.013(2) N37 0.036(2) 0.057(3) 0.045(2) -0.010(2) 0.0041(18) -0.009(2) C41 0.025(2) 0.038(2) 0.030(2) -0.0078(19) 0.0042(17) -0.0129(19) N41 0.034(2) 0.029(2) 0.035(2) -0.0068(17) -0.0014(16) -0.0124(18) C42 0.034(2) 0.037(3) 0.037(2) -0.009(2) 0.004(2) -0.011(2) C43 0.037(3) 0.041(3) 0.034(2) -0.005(2) -0.002(2) -0.011(2) C44 0.038(3) 0.052(3) 0.040(3) -0.005(2) -0.005(2) -0.008(2) C45 0.040(3) 0.050(3) 0.047(3) -0.019(2) -0.001(2) -0.013(2) C46 0.029(2) 0.040(3) 0.044(3) -0.010(2) -0.003(2) -0.009(2) _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 N11 C12 1.342(5) . ? N11 C19 1.372(5) . ? N11 H11 0.91(5) . ? C12 N13 1.328(5) . ? C12 H12 0.9500 . ? N13 C14 1.394(5) . ? C14 N15 1.325(5) . ? C14 C19 1.392(6) . ? N15 C16 1.352(5) . ? C16 C17 1.385(6) . ? C16 H16 0.9500 . ? C17 C18 1.386(6) . ? C17 H17 0.9500 . ? C18 C19 1.381(6) . ? C18 H18 0.9500 . ? C21 O21 1.238(5) . ? C21 N41 1.348(5) . ? C21 N31 1.378(5) . ? C31 C36 1.388(6) . ? C31 C32 1.394(6) . ? C31 N31 1.404(5) . ? N31 H31 0.92(4) . ? C32 C33 1.383(6) . ? C32 C37 1.453(6) . ? C33 C34 1.400(6) . ? C33 H33 0.9500 . ? C34 C35 1.382(6) . ? C34 H34 0.9500 . ? C35 C36 1.384(6) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N37 1.143(5) . ? C41 C46 1.396(6) . ? C41 C42 1.397(6) . ? C41 N41 1.413(5) . ? N41 H41 0.75(5) . ? C42 C43 1.361(6) . ? C42 H42 0.9500 . ? C43 C44 1.389(6) . ? C43 H43 0.9500 . ? C44 C45 1.377(6) . ? C44 H44 0.9500 . ? C45 C46 1.363(6) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? 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 C12 N11 C19 106.8(4) . . ? C12 N11 H11 138(3) . . ? C19 N11 H11 113(3) . . ? N13 C12 N11 114.1(4) . . ? N13 C12 H12 123.0 . . ? N11 C12 H12 123.0 . . ? C12 N13 C14 103.3(4) . . ? N15 C14 C19 125.1(4) . . ? N15 C14 N13 124.7(4) . . ? C19 C14 N13 110.1(4) . . ? C14 N15 C16 114.5(4) . . ? N15 C16 C17 123.8(4) . . ? N15 C16 H16 118.1 . . ? C17 C16 H16 118.1 . . ? C16 C17 C18 121.1(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 115.0(4) . . ? C19 C18 H18 122.5 . . ? C17 C18 H18 122.5 . . ? N11 C19 C18 134.0(4) . . ? N11 C19 C14 105.6(4) . . ? C18 C19 C14 120.4(4) . . ? O21 C21 N41 124.9(4) . . ? O21 C21 N31 120.8(4) . . ? N41 C21 N31 114.2(4) . . ? C36 C31 C32 118.2(4) . . ? C36 C31 N31 118.5(4) . . ? C32 C31 N31 123.2(4) . . ? C21 N31 C31 124.7(4) . . ? C21 N31 H31 114(3) . . ? C31 N31 H31 120(3) . . ? C33 C32 C31 122.1(4) . . ? C33 C32 C37 118.0(4) . . ? C31 C32 C37 119.8(4) . . ? C32 C33 C34 118.9(4) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C35 C34 C33 119.2(4) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? C34 C35 C36 121.3(4) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C35 C36 C31 120.3(4) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? N37 C37 C32 174.9(5) . . ? C46 C41 C42 118.0(4) . . ? C46 C41 N41 117.1(4) . . ? C42 C41 N41 124.9(4) . . ? C21 N41 C41 128.1(4) . . ? C21 N41 H41 127(4) . . ? C41 N41 H41 105(4) . . ? C43 C42 C41 120.5(4) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C42 C43 C44 120.8(4) . . ? C42 C43 H43 119.6 . . ? C44 C43 H43 119.6 . . ? C45 C44 C43 119.3(4) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? C46 C45 C44 120.2(4) . . ? C46 C45 H45 119.9 . . ? C44 C45 H45 119.9 . . ? C45 C46 C41 121.2(4) . . ? C45 C46 H46 119.4 . . ? C41 C46 H46 119.4 . . ? 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 C19 N11 C12 N13 -0.2(5) . . . . ? N11 C12 N13 C14 0.6(4) . . . . ? C12 N13 C14 N15 -179.9(4) . . . . ? C12 N13 C14 C19 -0.8(4) . . . . ? C19 C14 N15 C16 0.2(5) . . . . ? N13 C14 N15 C16 179.2(4) . . . . ? C14 N15 C16 C17 1.2(6) . . . . ? N15 C16 C17 C18 -1.0(7) . . . . ? C16 C17 C18 C19 -0.6(6) . . . . ? C12 N11 C19 C18 -178.3(4) . . . . ? C12 N11 C19 C14 -0.3(4) . . . . ? C17 C18 C19 N11 179.7(4) . . . . ? C17 C18 C19 C14 1.9(6) . . . . ? N15 C14 C19 N11 179.8(3) . . . . ? N13 C14 C19 N11 0.7(4) . . . . ? N15 C14 C19 C18 -1.9(6) . . . . ? N13 C14 C19 C18 179.1(3) . . . . ? O21 C21 N31 C31 1.1(6) . . . . ? N41 C21 N31 C31 -176.7(3) . . . . ? C36 C31 N31 C21 -127.5(4) . . . . ? C32 C31 N31 C21 56.5(5) . . . . ? C36 C31 C32 C33 1.6(6) . . . . ? N31 C31 C32 C33 177.6(4) . . . . ? C36 C31 C32 C37 -175.4(4) . . . . ? N31 C31 C32 C37 0.6(6) . . . . ? C31 C32 C33 C34 -2.5(6) . . . . ? C37 C32 C33 C34 174.5(4) . . . . ? C32 C33 C34 C35 1.4(6) . . . . ? C33 C34 C35 C36 0.6(6) . . . . ? C34 C35 C36 C31 -1.5(6) . . . . ? C32 C31 C36 C35 0.4(6) . . . . ? N31 C31 C36 C35 -175.8(3) . . . . ? C33 C32 C37 N37 -38(5) . . . . ? C31 C32 C37 N37 139(5) . . . . ? O21 C21 N41 C41 9.2(6) . . . . ? N31 C21 N41 C41 -173.1(3) . . . . ? C46 C41 N41 C21 -179.5(4) . . . . ? C42 C41 N41 C21 1.6(6) . . . . ? C46 C41 C42 C43 -0.5(6) . . . . ? N41 C41 C42 C43 178.3(4) . . . . ? C41 C42 C43 C44 1.2(6) . . . . ? C42 C43 C44 C45 -1.2(6) . . . . ? C43 C44 C45 C46 0.4(7) . . . . ? C44 C45 C46 C41 0.3(6) . . . . ? C42 C41 C46 C45 -0.2(6) . . . . ? N41 C41 C46 C45 -179.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O21 0.91(5) 1.90(5) 2.771(5) 159(4) 1_545 N31 H31 N15 0.92(4) 2.01(5) 2.876(5) 158(4) . N41 H41 N13 0.75(5) 2.27(5) 3.009(5) 167(5) . _diffrn_measured_fraction_theta_max 0.768 _diffrn_reflns_theta_full 24.68 _diffrn_measured_fraction_theta_full 0.768 _refine_diff_density_max 0.317 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 937217'