# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Parthasarathi Dastidar' _publ_contact_author_address ; Analytical Science Discipline CSMCRI G B Marg Bhavnagar Gujarat 364002 INDIA ; _publ_contact_author_email PARTHOD123@REDIFFMAIL.COM _publ_section_title ; First Snapshot of A Nonpolymeric Hydrogelator Interacting with its Gelling solvents ; loop_ _publ_author_name 'Parthasarathi Dastidar' 'Amitava Das' 'D.Amilan Jose' 'D.Krishna Kumar' data_4pyuream _database_code_depnum_ccdc_archive 'CCDC 267563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 N4 O4' _chemical_formula_weight 294.31 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 ORTHORHOMBIC _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1836(7) _cell_length_b 10.6011(10) _cell_length_c 16.4345(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1425.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8692 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1956 _reflns_number_gt 1807 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics "PLATON, 'MERCURY 1.3" _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^)+(0.0591P)^2^+0.1149P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(12) _refine_ls_number_reflns 1956 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N 0.5850(2) 0.21771(16) 0.74367(10) 0.0188(4) Uani 1 1 d . . . C2 C 0.6418(3) 0.1744(2) 0.81485(13) 0.0200(4) Uani 1 1 d . . . C3 C 0.6140(3) 0.22965(19) 0.89009(12) 0.0176(4) Uani 1 1 d . . . C5 C 0.4538(3) 0.38261(19) 0.81907(12) 0.0179(4) Uani 1 1 d . . . C4 C 0.5182(2) 0.33869(17) 0.89258(11) 0.0145(4) Uani 1 1 d . . . C6 C 0.4919(3) 0.32150(18) 0.74769(13) 0.0186(4) Uani 1 1 d . . . N7 N 0.4816(2) 0.40675(15) 0.96279(9) 0.0155(3) Uani 1 1 d . . . H7 H 0.4083 0.4646 0.9586 0.019 Uiso 1 1 calc R . . C8 C 0.5515(2) 0.39026(18) 1.03830(11) 0.0140(4) Uani 1 1 d . . . O9 O 0.65696(18) 0.31182(13) 1.05298(9) 0.0182(3) Uani 1 1 d . . . N10 N 0.4912(2) 0.47472(15) 1.09450(10) 0.0158(3) Uani 1 1 d . . . C11 C 0.5404(2) 0.48594(18) 1.17549(11) 0.0149(4) Uani 1 1 d . . . C12 C 0.6670(2) 0.4181(2) 1.21202(12) 0.0177(4) Uani 1 1 d . . . C13 C 0.6962(3) 0.4361(2) 1.29446(12) 0.0193(4) Uani 1 1 d . . . N14 N 0.6120(2) 0.51538(17) 1.34214(10) 0.0198(4) Uani 1 1 d . . . C15 C 0.4947(3) 0.5833(2) 1.30564(13) 0.0216(4) Uani 1 1 d . . . C16 C 0.4567(3) 0.5728(2) 1.22393(12) 0.0191(4) Uani 1 1 d . . . O17 O 0.66253(18) 0.13822(13) 0.59128(9) 0.0194(3) Uani 1 1 d . . . C18 C 0.7946(3) 0.2152(2) 0.56475(12) 0.0177(4) Uani 1 1 d . . . C19 C 0.7950(3) 0.2199(2) 0.47318(13) 0.0190(4) Uani 1 1 d . . . O20 O 0.80598(19) 0.09702(14) 0.43725(8) 0.0192(3) Uani 1 1 d . . . O21 O 0.59046(19) 0.50158(15) 1.51039(9) 0.0218(3) Uani 1 1 d . . . H2 H 0.707(3) 0.097(2) 0.8122(14) 0.023(6) Uiso 1 1 d . . . H3 H 0.654(3) 0.197(2) 0.9365(16) 0.022(6) Uiso 1 1 d . . . H5 H 0.387(4) 0.455(3) 0.8205(18) 0.039(8) Uiso 1 1 d . . . H6 H 0.451(3) 0.351(2) 1.6976(15) 0.015(6) Uiso 1 1 d . . . H10 H 0.403(3) 0.518(2) 1.0832(15) 0.022(6) Uiso 1 1 d . . . H12 H 0.726(3) 0.357(2) 1.1862(15) 0.021(6) Uiso 1 1 d . . . H13 H 0.784(3) 0.391(2) 1.3211(15) 0.027(7) Uiso 1 1 d . . . H15 H 0.433(3) 0.643(2) 1.3395(16) 0.026(7) Uiso 1 1 d . . . H16 H 0.371(3) 0.622(2) 1.2022(14) 0.017(6) Uiso 1 1 d . . . H17 H 0.639(3) 0.164(2) 0.6411(18) 0.026(7) Uiso 1 1 d . . . H18A H 0.897(3) 0.179(2) 0.5837(15) 0.016(6) Uiso 1 1 d . . . H18B H 0.782(3) 0.296(2) 0.5857(16) 0.024(6) Uiso 1 1 d . . . H19A H 0.880(3) 0.275(2) 1.4537(14) 0.020(6) Uiso 1 1 d . . . H19B H 0.695(3) 0.258(2) 0.4547(15) 0.023(6) Uiso 1 1 d . . . H20 H 0.898(4) 0.066(3) 0.4540(18) 0.038(8) Uiso 1 1 d . . . H21A H 0.601(3) 0.503(2) 1.4576(18) 0.030(7) Uiso 1 1 d . . . H21B H 0.630(4) 0.565(3) 1.530(2) 0.052(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0208(9) 0.0217(8) 0.0138(8) -0.0031(7) 0.0021(7) -0.0013(7) C2 0.0208(10) 0.0207(10) 0.0186(10) -0.0023(8) -0.0001(8) 0.0043(8) C3 0.0209(10) 0.0182(9) 0.0136(9) 0.0008(8) -0.0024(8) 0.0008(8) C5 0.0217(10) 0.0162(9) 0.0157(9) -0.0005(8) -0.0036(8) 0.0012(8) C4 0.0158(9) 0.0167(9) 0.0109(8) -0.0016(7) 0.0005(7) -0.0036(7) C6 0.0240(10) 0.0195(9) 0.0124(9) 0.0006(7) -0.0013(8) -0.0029(8) N7 0.0170(8) 0.0166(8) 0.0129(8) -0.0009(6) -0.0002(6) 0.0033(7) C8 0.0141(8) 0.0153(9) 0.0126(9) -0.0012(7) 0.0015(7) -0.0023(7) O9 0.0216(7) 0.0189(7) 0.0140(7) -0.0005(5) -0.0013(6) 0.0040(6) N10 0.0155(8) 0.0184(8) 0.0135(8) -0.0012(7) -0.0009(6) 0.0020(7) C11 0.0161(8) 0.0157(8) 0.0128(9) 0.0007(7) 0.0014(7) -0.0049(7) C12 0.0174(9) 0.0199(9) 0.0159(9) -0.0034(8) -0.0001(8) 0.0005(8) C13 0.0193(9) 0.0214(10) 0.0172(10) 0.0011(8) -0.0014(8) -0.0012(8) N14 0.0211(8) 0.0239(9) 0.0145(8) -0.0021(7) -0.0005(7) -0.0033(7) C15 0.0238(10) 0.0226(10) 0.0185(10) -0.0055(8) 0.0021(8) -0.0005(9) C16 0.0184(9) 0.0203(9) 0.0187(10) -0.0013(8) -0.0003(8) 0.0030(8) O17 0.0244(7) 0.0210(7) 0.0129(7) -0.0038(6) 0.0047(6) -0.0058(6) C18 0.0186(10) 0.0185(9) 0.0161(9) -0.0022(8) 0.0011(8) -0.0028(8) C19 0.0193(9) 0.0195(10) 0.0181(9) 0.0020(8) 0.0003(8) -0.0030(9) O20 0.0171(7) 0.0265(8) 0.0140(7) -0.0038(6) -0.0006(6) -0.0001(6) O21 0.0241(8) 0.0271(9) 0.0142(7) -0.0036(6) 0.0017(6) -0.0044(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.340(3) . ? N1 C2 1.340(3) . ? C2 N1 1.340(3) 1 ? C2 C3 1.387(3) . ? C2 H2 0.98(3) . ? C3 C4 1.397(3) . ? C3 H3 0.90(3) . ? C5 C6 1.376(3) . ? C5 C4 1.398(3) . ? C5 H5 0.94(3) . ? C4 N7 1.393(2) . ? C6 N1 1.340(3) 1 ? N7 C8 1.378(2) . ? N7 H7 0.8600 . ? C8 O9 1.223(2) . ? C8 N10 1.378(2) . ? N10 C11 1.396(2) . ? N10 H10 0.88(3) . ? C11 C16 1.397(3) . ? C11 C12 1.397(3) . ? C12 C13 1.389(3) . ? C12 H12 0.91(3) . ? C13 N14 1.340(3) 1 ? C13 N14 1.340(3) . ? C13 H13 0.97(3) . ? N14 C15 1.342(3) . ? C15 N14 1.342(3) 1 ? C15 C16 1.383(3) . ? C15 H15 0.98(3) . ? C16 H16 0.94(2) . ? O17 C18 1.423(2) . ? O17 H17 0.88(3) . ? C18 C19 1.506(3) . ? C18 H18A 0.98(2) . ? C18 H18B 0.92(3) . ? C19 O20 1.433(2) . ? C19 H19B 0.96(3) . ? O20 H20 0.87(3) . ? O21 H21A 0.87(3) . ? O21 H21B 0.81(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 N1 N1 C6 0(10) 1 . ? N1 N1 C2 0(10) 1 . ? C6 N1 C2 115.83(18) . . ? N1 C2 C3 125.19(19) 1 . ? N1 C2 C3 125.19(19) . . ? N1 C2 H2 115.9(14) 1 . ? N1 C2 H2 115.9(14) . . ? C3 C2 H2 118.9(14) . . ? C2 C3 C4 117.90(18) . . ? C2 C3 H3 122.3(16) . . ? C4 C3 H3 119.8(16) . . ? C6 C5 C4 119.65(18) . . ? C6 C5 H5 122.4(18) . . ? C4 C5 H5 117.9(18) . . ? N7 C4 C5 117.52(17) . . ? N7 C4 C3 124.98(17) . . ? C5 C4 C3 117.50(18) . . ? N1 C6 C5 123.88(19) 1 . ? N1 C6 C5 123.88(19) . . ? C8 N7 C4 126.22(16) . . ? C8 N7 H7 116.9 . . ? C4 N7 H7 116.9 . . ? O9 C8 N10 124.24(17) . . ? O9 C8 N7 123.86(17) . . ? N10 C8 N7 111.88(17) . . ? C8 N10 C11 126.25(17) . . ? C8 N10 H10 119.6(16) . . ? C11 N10 H10 113.3(16) . . ? N10 C11 C16 117.28(18) . . ? N10 C11 C12 125.46(18) . . ? C16 C11 C12 117.27(18) . . ? C13 C12 C11 118.43(19) . . ? C13 C12 H12 117.5(15) . . ? C11 C12 H12 123.8(15) . . ? N14 C13 C12 124.6(2) 1 . ? N14 C13 C12 124.6(2) . . ? N14 C13 H13 115.4(15) 1 . ? N14 C13 H13 115.4(15) . . ? C12 C13 H13 120.0(15) . . ? N14 N14 C13 0(10) 1 . ? N14 N14 C15 0(10) 1 . ? C13 N14 C15 116.30(18) . . ? N14 C15 C16 123.5(2) 1 . ? N14 C15 C16 123.5(2) . . ? N14 C15 H15 117.4(15) 1 . ? N14 C15 H15 117.4(15) . . ? C16 C15 H15 119.1(15) . . ? C15 C16 C11 119.74(19) . . ? C15 C16 H16 119.4(14) . . ? C11 C16 H16 120.8(14) . . ? C18 O17 H17 106.0(17) . . ? O17 C18 C19 109.09(17) . . ? O17 C18 H18A 109.2(13) . . ? C19 C18 H18A 109.2(14) . . ? O17 C18 H18B 109.2(16) . . ? C19 C18 H18B 110.0(16) . . ? H18A C18 H18B 110(2) . . ? O20 C19 C18 112.44(17) . . ? O20 C19 H19B 107.9(15) . . ? C18 C19 H19B 109.1(15) . . ? C19 O20 H20 106(2) . . ? H21A O21 H21B 110(3) . . ? 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 N7 H7 O17 0.86 2.10 2.864(2) 148.2 3_656 N10 H10 O20 0.88(3) 1.93(3) 2.805(2) 173(2) 3_656 O17 H17 N1 0.88(3) 1.83(3) 2.717(2) 179(3) 1 O20 H20 O21 0.87(3) 1.83(3) 2.693(2) 179(3) 4_557 O21 H21A N14 0.87(3) 1.90(3) 2.775(2) 176(3) 1 O21 H21B O9 0.81(4) 2.21(4) 2.945(2) 150(3) 2_665 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.277 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048 data_ureahclm _database_code_depnum_ccdc_archive 'CCDC 267564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Cl2 N8 O5.32' _chemical_formula_weight 560.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8236(12) _cell_length_b 10.2628(12) _cell_length_c 13.9993(17) _cell_angle_alpha 101.696(2) _cell_angle_beta 95.602(2) _cell_angle_gamma 101.734(2) _cell_volume 1338.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 585 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7687 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5734 _reflns_number_gt 4359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics "PLATON, 'MERCURY 1.3" _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^)+(0.0818P)^2^+0.7564P] 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 5734 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1639 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.33706(7) 0.26407(7) 0.50500(5) 0.02597(19) Uani 1 1 d . . . Cl2 Cl 0.26537(7) 0.26376(7) 0.79793(5) 0.02388(19) Uani 1 1 d . . . N1 N 0.3969(2) 0.8781(2) 1.07194(17) 0.0212(5) Uani 1 1 d . . . H1 H 0.4491 0.9528 1.1080 0.025 Uiso 1 1 calc R . . C2 C 0.2586(3) 0.8672(3) 1.0512(2) 0.0208(6) Uani 1 1 d . . . H2 H 0.2212 0.9412 1.0760 0.025 Uiso 1 1 calc R . . C3 C 0.1703(3) 0.7498(3) 0.99421(19) 0.0186(5) Uani 1 1 d . . . H3 H 0.0743 0.7436 0.9812 0.022 Uiso 1 1 calc R . . C4 C 0.2286(3) 0.6391(3) 0.95607(19) 0.0168(5) Uani 1 1 d . . . C5 C 0.3743(3) 0.6530(3) 0.9794(2) 0.0189(6) Uani 1 1 d . . . H5 H 0.4153 0.5811 0.9557 0.023 Uiso 1 1 calc R . . C6 C 0.4555(3) 0.7731(3) 1.0370(2) 0.0230(6) Uani 1 1 d . . . H6 H 0.5518 0.7825 1.0521 0.028 Uiso 1 1 calc R . . N7 N 0.1541(2) 0.5183(2) 0.89685(17) 0.0182(5) Uani 1 1 d . . . C8 C 0.0092(3) 0.4790(3) 0.86665(19) 0.0179(5) Uani 1 1 d . . . O9 O -0.07233(19) 0.54962(19) 0.89013(15) 0.0247(5) Uani 1 1 d . . . N10 N -0.0259(2) 0.3488(2) 0.80847(17) 0.0175(5) Uani 1 1 d . . . C11 C -0.1595(3) 0.2740(3) 0.76441(18) 0.0159(5) Uani 1 1 d . . . C12 C -0.2793(3) 0.3274(3) 0.76048(19) 0.0177(5) Uani 1 1 d . . . H12 H -0.2746 0.4187 0.7886 0.021 Uiso 1 1 calc R . . C13 C -0.4058(3) 0.2398(3) 0.71319(19) 0.0191(5) Uani 1 1 d . . . H13 H -0.4855 0.2753 0.7104 0.023 Uiso 1 1 calc R . . N14 N -0.4198(2) 0.1069(2) 0.67133(16) 0.0189(5) Uani 1 1 d . . . C15 C -0.3033(3) 0.0579(3) 0.6757(2) 0.0204(6) Uani 1 1 d . . . H15 H -0.3109 -0.0336 0.6465 0.025 Uiso 1 1 calc R . . C16 C -0.1732(3) 0.1355(3) 0.72094(19) 0.0194(6) Uani 1 1 d . . . H16 H -0.0956 0.0967 0.7226 0.023 Uiso 1 1 calc R . . N14' N 0.4440(2) 0.8790(2) 0.81550(17) 0.0216(5) Uani 1 1 d . . . C15' C 0.3041(3) 0.8508(3) 0.7974(2) 0.0200(6) Uani 1 1 d . . . H15' H 0.2594 0.9180 0.8249 0.024 Uiso 1 1 calc R . . C16' C 0.2205(3) 0.7299(3) 0.74089(19) 0.0179(5) Uani 1 1 d . . . H16' H 0.1232 0.7164 0.7306 0.022 Uiso 1 1 calc R . . C11' C 0.2872(3) 0.6276(3) 0.69935(19) 0.0170(5) Uani 1 1 d . . . C12' C 0.4339(3) 0.6551(3) 0.7179(2) 0.0218(6) Uani 1 1 d . . . H12' H 0.4816 0.5899 0.6915 0.026 Uiso 1 1 calc R . . C13' C 0.5069(3) 0.7796(3) 0.7755(2) 0.0233(6) Uani 1 1 d . . . H13' H 0.6044 0.7962 0.7876 0.028 Uiso 1 1 calc R . . N10' N 0.2186(2) 0.5012(2) 0.63974(17) 0.0180(5) Uani 1 1 d . . . C8' C 0.0768(3) 0.4536(3) 0.60895(19) 0.0162(5) Uani 1 1 d . . . O9' O -0.01216(19) 0.51665(19) 0.63105(14) 0.0219(4) Uani 1 1 d . . . N7' N 0.0483(2) 0.3228(2) 0.55038(17) 0.0165(5) Uani 1 1 d . . . C4' C -0.0812(3) 0.2423(3) 0.50522(18) 0.0159(5) Uani 1 1 d . . . C5' C -0.2103(3) 0.2780(3) 0.51543(19) 0.0162(5) Uani 1 1 d . . . H5' H -0.2136 0.3633 0.5524 0.019 Uiso 1 1 calc R . . C6' C -0.3318(3) 0.1849(3) 0.46988(18) 0.0164(5) Uani 1 1 d . . . H6' H -0.4178 0.2078 0.4768 0.020 Uiso 1 1 calc R . . N1' N -0.3298(2) 0.0615(2) 0.41565(16) 0.0181(5) Uani 1 1 d . . . H1' H -0.4077 0.0048 0.3888 0.022 Uiso 1 1 calc R . . C2' C -0.2072(3) 0.0255(3) 0.4028(2) 0.0195(6) Uani 1 1 d . . . H2' H -0.2075 -0.0598 0.3642 0.023 Uiso 1 1 calc R . . C3' C -0.0818(3) 0.1137(3) 0.4462(2) 0.0187(6) Uani 1 1 d . . . H3' H 0.0025 0.0886 0.4367 0.022 Uiso 1 1 calc R . . O1 O 0.2094(3) 0.3275(3) 0.3040(2) 0.0525(8) Uani 1 1 d . . . O3 O 0.1271(4) 0.0954(4) 0.9422(3) 0.0591(9) Uani 1 1 d . . . O2 O 0.1067(3) 0.1157(3) 0.1388(2) 0.0445(7) Uani 1 1 d . . . H7' H 0.116(4) 0.296(3) 0.531(2) 0.025(9) Uiso 1 1 d . . . H7 H 0.200(3) 0.462(3) 0.884(2) 0.014(7) Uiso 1 1 d . . . H10 H 0.041(4) 0.304(4) 0.799(2) 0.032(9) Uiso 1 1 d . . . H10' H 0.269(4) 0.452(4) 0.616(2) 0.029(9) Uiso 1 1 d . . . H1A H 0.225(6) 0.285(6) 0.359(4) 0.12(2) Uiso 1 1 d . . . H1B H 0.151(4) 0.380(4) 0.317(3) 0.034(10) Uiso 1 1 d . . . H2A H 0.129(5) 0.191(5) 0.195(4) 0.067(14) Uiso 1 1 d . . . H2B H 0.113(3) 0.140(3) 0.086(3) 0.023(9) Uiso 1 1 d . . . H3A H 0.174(6) 0.133(6) 0.908(4) 0.079(19) Uiso 1 1 d . . . H3B H 0.076(6) 0.035(6) 0.905(4) 0.08(2) Uiso 1 1 d . . . O1W O 0.602(2) 0.479(2) 0.5738(15) 0.072(6) Uiso 0.16 1 d P . . O2W O -0.315(2) 0.636(2) 0.9323(17) 0.074(6) Uiso 0.16 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0201(4) 0.0272(4) 0.0293(4) -0.0011(3) 0.0057(3) 0.0091(3) Cl2 0.0190(3) 0.0252(4) 0.0246(4) -0.0023(3) 0.0029(3) 0.0066(3) N1 0.0204(12) 0.0162(11) 0.0178(11) -0.0062(9) -0.0022(9) -0.0043(9) C2 0.0260(15) 0.0154(13) 0.0175(13) -0.0010(11) 0.0034(11) 0.0017(11) C3 0.0164(13) 0.0183(13) 0.0175(13) -0.0007(11) 0.0014(10) 0.0013(10) C4 0.0172(13) 0.0142(12) 0.0147(12) -0.0013(10) 0.0006(10) -0.0011(10) C5 0.0195(14) 0.0161(13) 0.0189(13) 0.0007(11) 0.0002(10) 0.0033(10) C6 0.0186(14) 0.0260(15) 0.0212(14) 0.0058(12) -0.0026(11) 0.0003(11) N7 0.0131(11) 0.0143(11) 0.0222(12) -0.0051(9) 0.0010(9) 0.0014(9) C8 0.0126(12) 0.0201(13) 0.0169(13) 0.0007(11) 0.0004(10) -0.0013(10) O9 0.0161(10) 0.0201(10) 0.0311(11) -0.0058(9) -0.0007(8) 0.0022(8) N10 0.0126(11) 0.0131(11) 0.0212(12) -0.0064(9) 0.0003(9) 0.0011(8) C11 0.0165(13) 0.0157(13) 0.0117(12) -0.0001(10) 0.0008(9) -0.0012(10) C12 0.0161(13) 0.0182(13) 0.0146(12) -0.0012(10) 0.0011(10) 0.0003(10) C13 0.0169(13) 0.0219(14) 0.0160(13) 0.0008(11) 0.0022(10) 0.0023(10) N14 0.0156(11) 0.0213(12) 0.0146(11) 0.0011(9) -0.0013(9) -0.0032(9) C15 0.0199(14) 0.0185(13) 0.0183(13) -0.0003(11) 0.0000(10) -0.0003(10) C16 0.0153(13) 0.0214(14) 0.0185(13) 0.0000(11) 0.0008(10) 0.0029(10) N14' 0.0216(12) 0.0182(12) 0.0182(12) -0.0038(9) -0.0006(9) -0.0015(9) C15' 0.0218(14) 0.0154(13) 0.0185(13) -0.0013(11) 0.0022(11) 0.0003(10) C16' 0.0178(13) 0.0151(12) 0.0174(13) -0.0016(10) 0.0026(10) 0.0012(10) C11' 0.0171(13) 0.0146(12) 0.0153(12) 0.0000(10) -0.0003(10) -0.0012(10) C12' 0.0161(13) 0.0187(13) 0.0258(15) -0.0019(11) -0.0009(11) 0.0016(10) C13' 0.0155(13) 0.0205(14) 0.0278(15) 0.0006(12) -0.0011(11) -0.0025(10) N10' 0.0153(11) 0.0127(11) 0.0212(12) -0.0054(9) 0.0001(9) 0.0025(9) C8' 0.0128(12) 0.0172(13) 0.0145(12) -0.0005(10) -0.0008(9) -0.0008(10) O9' 0.0146(9) 0.0184(10) 0.0280(11) -0.0034(8) 0.0014(8) 0.0025(7) N7' 0.0094(10) 0.0147(11) 0.0202(11) -0.0049(9) -0.0003(9) 0.0010(8) C4' 0.0145(12) 0.0171(13) 0.0130(12) 0.0016(10) 0.0013(9) -0.0008(10) C5' 0.0153(13) 0.0152(13) 0.0158(12) 0.0007(10) 0.0015(10) 0.0016(10) C6' 0.0141(12) 0.0188(13) 0.0149(12) 0.0029(10) 0.0025(10) 0.0015(10) N1' 0.0144(11) 0.0182(11) 0.0164(11) 0.0017(9) -0.0022(8) -0.0039(8) C2' 0.0220(14) 0.0139(12) 0.0186(13) -0.0015(10) 0.0013(11) 0.0009(10) C3' 0.0151(13) 0.0165(13) 0.0213(14) -0.0014(11) 0.0012(10) 0.0027(10) O1 0.0620(19) 0.068(2) 0.0352(15) -0.0002(14) 0.0032(13) 0.0468(16) O3 0.067(2) 0.054(2) 0.054(2) 0.0260(17) 0.0043(17) -0.0024(17) O2 0.0554(17) 0.0376(15) 0.0399(16) 0.0044(13) -0.0008(13) 0.0171(12) _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 N1 C2 1.338(4) . ? N1 C6 1.351(4) . ? N1 H1 0.8600 . ? C2 C3 1.375(4) . ? C2 H2 0.9300 . ? C3 C4 1.407(4) . ? C3 H3 0.9300 . ? C4 N7 1.362(3) . ? C4 C5 1.409(4) . ? C5 C6 1.370(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.396(3) . ? N7 H7 0.81(3) . ? C8 O9 1.210(3) . ? C8 N10 1.373(3) . ? N10 C11 1.391(3) . ? N10 H10 0.88(4) . ? C11 C12 1.396(4) . ? C11 C16 1.401(4) . ? C12 C13 1.391(4) . ? C12 H12 0.9300 . ? C13 N14 1.344(3) . ? C13 H13 0.9300 . ? N14 C15 1.341(4) . ? C15 C16 1.376(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N14' C15' 1.334(4) . ? N14' C13' 1.352(4) . ? C15' C16' 1.379(4) . ? C15' H15' 0.9300 . ? C16' C11' 1.405(4) . ? C16' H16' 0.9300 . ? C11' N10' 1.389(3) . ? C11' C12' 1.398(4) . ? C12' C13' 1.377(4) . ? C12' H12' 0.9300 . ? C13' H13' 0.9300 . ? N10' C8' 1.373(3) . ? N10' H10' 0.82(4) . ? C8' O9' 1.217(3) . ? C8' N7' 1.381(3) . ? N7' C4' 1.379(3) . ? N7' H7' 0.82(3) . ? C4' C5' 1.403(4) . ? C4' C3' 1.406(4) . ? C5' C6' 1.373(3) . ? C5' H5' 0.9300 . ? C6' N1' 1.343(3) . ? C6' H6' 0.9300 . ? N1' C2' 1.348(4) . ? N1' H1' 0.8600 . ? C2' C3' 1.372(4) . ? C2' H2' 0.9300 . ? C3' H3' 0.9300 . ? O1 H1A 0.97(6) . ? O1 H1B 0.88(4) . ? O3 H3A 0.79(6) . ? O3 H3B 0.77(6) . ? O2 H2A 0.95(5) . ? O2 H2B 0.82(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 C2 N1 C6 120.9(2) . . ? C2 N1 H1 119.6 . . ? C6 N1 H1 119.6 . . ? N1 C2 C3 121.9(3) . . ? N1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C2 C3 C4 118.5(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? N7 C4 C3 124.7(2) . . ? N7 C4 C5 116.9(2) . . ? C3 C4 C5 118.4(2) . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 120.6(3) . . ? N1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C4 N7 C8 127.4(2) . . ? C4 N7 H7 114(2) . . ? C8 N7 H7 118(2) . . ? O9 C8 N10 125.8(2) . . ? O9 C8 N7 124.4(2) . . ? N10 C8 N7 109.8(2) . . ? C8 N10 C11 127.1(2) . . ? C8 N10 H10 119(2) . . ? C11 N10 H10 114(2) . . ? N10 C11 C12 124.6(2) . . ? N10 C11 C16 117.0(2) . . ? C12 C11 C16 118.4(2) . . ? C13 C12 C11 117.9(2) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? N14 C13 C12 124.0(3) . . ? N14 C13 H13 118.0 . . ? C12 C13 H13 118.0 . . ? C15 N14 C13 117.0(2) . . ? N14 C15 C16 123.7(3) . . ? N14 C15 H15 118.2 . . ? C16 C15 H15 118.2 . . ? C15 C16 C11 118.9(3) . . ? C15 C16 H16 120.5 . . ? C11 C16 H16 120.5 . . ? C15' N14' C13' 116.6(2) . . ? N14' C15' C16' 125.0(3) . . ? N14' C15' H15' 117.5 . . ? C16' C15' H15' 117.5 . . ? C15' C16' C11' 117.8(2) . . ? C15' C16' H16' 121.1 . . ? C11' C16' H16' 121.1 . . ? N10' C11' C12' 117.1(2) . . ? N10' C11' C16' 125.0(2) . . ? C12' C11' C16' 118.0(2) . . ? C13' C12' C11' 119.3(3) . . ? C13' C12' H12' 120.3 . . ? C11' C12' H12' 120.3 . . ? N14' C13' C12' 123.3(3) . . ? N14' C13' H13' 118.4 . . ? C12' C13' H13' 118.4 . . ? C8' N10' C11' 127.5(2) . . ? C8' N10' H10' 116(2) . . ? C11' N10' H10' 116(2) . . ? O9' C8' N10' 124.9(2) . . ? O9' C8' N7' 124.4(2) . . ? N10' C8' N7' 110.7(2) . . ? C4' N7' C8' 127.6(2) . . ? C4' N7' H7' 115(2) . . ? C8' N7' H7' 116(2) . . ? N7' C4' C5' 125.1(2) . . ? N7' C4' C3' 116.6(2) . . ? C5' C4' C3' 118.3(2) . . ? C6' C5' C4' 118.8(2) . . ? C6' C5' H5' 120.6 . . ? C4' C5' H5' 120.6 . . ? N1' C6' C5' 121.7(2) . . ? N1' C6' H6' 119.1 . . ? C5' C6' H6' 119.1 . . ? C6' N1' C2' 120.8(2) . . ? C6' N1' H1' 119.6 . . ? C2' N1' H1' 119.6 . . ? N1' C2' C3' 120.5(2) . . ? N1' C2' H2' 119.8 . . ? C3' C2' H2' 119.8 . . ? C2' C3' C4' 119.8(2) . . ? C2' C3' H3' 120.1 . . ? C4' C3' H3' 120.1 . . ? H1A O1 H1B 109(4) . . ? H3A O3 H3B 103(5) . . ? H2A O2 H2B 113(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 N1 H1 N14' 0.86 1.88 2.736(3) 176.9 2_677 N1' H1' N14 0.86 1.85 2.712(3) 175.9 2_456 N7' H7' Cl1 0.82(3) 2.31(3) 3.116(2) 166(3) 1 N7 H7 Cl2 0.81(3) 2.38(3) 3.151(2) 159(3) 1 N10 H10 Cl2 0.88(4) 2.32(4) 3.164(2) 159(3) 1 N10' H10' Cl1 0.82(4) 2.48(4) 3.249(2) 159(3) 1 O1 H1A Cl1 0.97(6) 2.30(6) 3.209(3) 156(5) 1 O1 H1B O9' 0.88(4) 1.99(4) 2.856(3) 169(3) 2_566 O2 H2A O1 0.95(5) 1.84(5) 2.776(4) 168(4) 1 O2 H2B O3 0.82(4) 2.00(4) 2.748(5) 150(3) 1_554 O3 H3A Cl2 0.79(6) 2.37(6) 3.148(4) 167(5) 1 O3 H3B O2 0.77(6) 2.07(6) 2.779(5) 153(6) 2_556 _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 0.691 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.096 data_kb377dr _database_code_depnum_ccdc_archive 'CCDC 267565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N4 O' _chemical_formula_weight 214.23 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 ORTHORHOMBIC _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 13.713(6) _cell_length_b 6.977(3) _cell_length_c 10.013(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 957.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2651 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.26 _reflns_number_total 592 _reflns_number_gt 583 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics "PLATON, 'MERCURY 1.3" _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^)+(0.0638P)^2^+0.1905P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 592 _refine_ls_number_parameters 94 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.099 _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 O9 O 0.5000 0.0000 0.72785(19) 0.0236(5) Uani 1 2 d S . . C8 C 0.5000 0.0000 0.8501(3) 0.0162(5) Uani 1 2 d S . . N7 N 0.45025(12) 0.1325(2) 0.92547(16) 0.0177(4) Uani 1 1 d . . . N1 N 0.36917(10) 0.5234(2) 0.69934(17) 0.0198(4) Uani 1 1 d . . . C5 C 0.32831(13) 0.5998(3) 0.9255(2) 0.0204(4) Uani 1 1 d . . . C6 C 0.32999(13) 0.6420(3) 0.7900(2) 0.0207(4) Uani 1 1 d . . . C4 C 0.36936(13) 0.4297(3) 0.9698(2) 0.0183(4) Uani 1 1 d . . . C3 C 0.40901(12) 0.3024(3) 0.87642(19) 0.0156(4) Uani 1 1 d . . . C2 C 0.40639(14) 0.3554(3) 0.7414(2) 0.0190(4) Uani 1 1 d . . . H2 H 0.4331(17) 0.272(4) 0.678(3) 0.023(7) Uiso 1 1 d . . . H6 H 0.3016(17) 0.768(4) 0.757(3) 0.026(6) Uiso 1 1 d . . . H5 H 0.2984(16) 0.685(4) 0.989(3) 0.021(6) Uiso 1 1 d . . . H4 H 0.3710(16) 0.396(4) 1.061(3) 0.017(5) Uiso 1 1 d . . . H7 H 0.4367(17) 0.104(4) 1.005(3) 0.019(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9 0.0365(10) 0.0179(9) 0.0163(11) 0.000 0.000 0.0050(8) C8 0.0213(11) 0.0137(11) 0.0137(14) 0.000 0.000 -0.0028(9) N7 0.0275(8) 0.0156(8) 0.0100(7) 0.0024(6) 0.0016(7) 0.0027(6) N1 0.0236(8) 0.0204(7) 0.0155(7) 0.0043(7) -0.0009(7) 0.0008(6) C5 0.0233(9) 0.0189(8) 0.0190(9) -0.0012(8) 0.0022(8) 0.0027(7) C6 0.0224(9) 0.0193(8) 0.0204(9) 0.0057(8) -0.0008(8) 0.0026(7) C4 0.0222(9) 0.0182(9) 0.0146(9) 0.0000(8) -0.0003(7) -0.0004(7) C3 0.0178(9) 0.0127(8) 0.0162(8) 0.0013(7) -0.0024(7) -0.0002(6) C2 0.0223(9) 0.0182(8) 0.0165(9) 0.0002(7) 0.0023(7) -0.0001(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 O9 C8 1.224(3) . ? C8 N7 1.375(2) 2_655 ? C8 N7 1.375(2) . ? N7 C3 1.403(2) . ? N7 H7 0.84(3) . ? N1 C6 1.340(3) . ? N1 C2 1.347(2) . ? C5 C4 1.387(3) . ? C5 C6 1.389(3) . ? C5 H5 0.96(3) . ? C6 H6 1.02(3) . ? C4 C3 1.399(3) . ? C4 H4 0.94(3) . ? C3 C2 1.401(3) . ? C2 H2 0.93(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 C8 N7 123.31(11) . 2_655 ? O9 C8 N7 123.31(11) . . ? N7 C8 N7 113.4(2) 2_655 . ? C8 N7 C3 125.19(18) . . ? C8 N7 H7 118.1(17) . . ? C3 N7 H7 116.2(17) . . ? C6 N1 C2 118.53(18) . . ? C4 C5 C6 119.16(19) . . ? C4 C5 H5 119.6(16) . . ? C6 C5 H5 121.2(16) . . ? N1 C6 C5 122.50(17) . . ? N1 C6 H6 117.6(16) . . ? C5 C6 H6 119.9(16) . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 122.1(16) . . ? C3 C4 H4 118.7(16) . . ? C4 C3 C2 117.85(17) . . ? C4 C3 N7 117.33(18) . . ? C2 C3 N7 124.81(17) . . ? N1 C2 C3 122.76(17) . . ? N1 C2 H2 118.6(17) . . ? C3 C2 H2 118.7(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 N1 0.84(3) 2.23(3) 3.055(3) 168(2) 5_545 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.252 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.052 data_kkb256g _database_code_depnum_ccdc_archive 'CCDC 267566' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16.50 H19 N6 O3.50' _chemical_formula_weight 357.38 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'C 2/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 13.073(4) _cell_length_b 11.793(7) _cell_length_c 22.678(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.03(3) _cell_angle_gamma 90.00 _cell_volume 3443(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description PLATE _exptl_crystal_colour 'PALE YELLOW' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OMEGA TWO THETA' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1HR _diffrn_standards_decay_% ? _diffrn_reflns_number 2239 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 22.45 _reflns_number_total 2239 _reflns_number_gt 1494 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-PC _computing_cell_refinement CAD4-PC _computing_data_reduction NRCVAX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.3' _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^)+(0.0581P)^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 2239 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _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 N1 N 0.14087(16) 0.33608(18) 0.26383(10) 0.0612(6) Uani 1 1 d . . . C2 C 0.1234(2) 0.2288(2) 0.27717(12) 0.0590(7) Uani 1 1 d . . . H2 H 0.0876(17) 0.2165(19) 0.3119(11) 0.071 Uiso 1 1 d . . . C3 C 0.15654(19) 0.1406(2) 0.24635(12) 0.0610(7) Uani 1 1 d . . . H3 H 0.1426 0.0665 0.2565 0.073 Uiso 1 1 calc R . . C4 C 0.21027(18) 0.16044(19) 0.20042(11) 0.0555(7) Uani 1 1 d . . . H4 H 0.2333 0.1005 0.1795 0.067 Uiso 1 1 calc R . . C5 C 0.22930(17) 0.27068(18) 0.18600(10) 0.0461(6) Uani 1 1 d . . . C6 C 0.1921(2) 0.3546(2) 0.21938(12) 0.0570(7) Uani 1 1 d . . . H6 H 0.2066(17) 0.429(2) 0.2080(10) 0.068 Uiso 1 1 d . . . N7 N 0.28251(16) 0.30471(16) 0.14057(9) 0.0533(6) Uani 1 1 d . . . C8 C 0.31431(17) 0.23846(18) 0.09779(10) 0.0446(6) Uani 1 1 d . . . O9 O 0.30688(13) 0.13576(12) 0.09657(7) 0.0564(5) Uani 1 1 d . . . N10 N 0.35472(15) 0.29944(16) 0.05666(9) 0.0502(5) Uani 1 1 d . . . C11 C 0.40395(17) 0.25813(17) 0.01136(10) 0.0448(6) Uani 1 1 d . . . C12 C 0.40715(18) 0.14670(18) -0.00633(11) 0.0538(7) Uani 1 1 d . . . H12 H 0.3742 0.0904 0.0122 0.065 Uiso 1 1 calc R . . C13 C 0.4598(2) 0.1203(2) -0.05167(11) 0.0616(7) Uani 1 1 d . . . H13 H 0.4635 0.0454 -0.0639 0.074 Uiso 1 1 calc R . . C14 C 0.5070(2) 0.2035(2) -0.07894(12) 0.0653(7) Uani 1 1 d . . . H14 H 0.5426 0.1835 -0.1095 0.078 Uiso 1 1 calc R . . N15 N 0.50405(16) 0.31210(17) -0.06367(10) 0.0631(6) Uani 1 1 d . . . C16 C 0.45325(18) 0.33700(19) -0.01965(12) 0.0551(7) Uani 1 1 d . . . H16 H 0.4503 0.4128 -0.0087 0.066 Uiso 1 1 calc R . . N17 N 0.68539(16) 0.20032(17) 0.08848(10) 0.0612(6) Uani 1 1 d . . . C18 C 0.6987(2) 0.3081(2) 0.07391(13) 0.0616(7) Uani 1 1 d . . . H18 H 0.738(2) 0.3197(19) 0.0419(12) 0.074 Uiso 1 1 d . . . C19 C 0.65795(19) 0.3960(2) 0.10136(11) 0.0592(7) Uani 1 1 d . . . H19 H 0.6685 0.4701 0.0898 0.071 Uiso 1 1 calc R . . C20 C 0.60125(19) 0.37571(18) 0.14607(11) 0.0549(7) Uani 1 1 d . . . H20 H 0.5725 0.4353 0.1645 0.066 Uiso 1 1 calc R . . C21 C 0.58796(17) 0.26495(17) 0.16291(11) 0.0444(6) Uani 1 1 d . . . C22 C 0.63169(19) 0.1815(2) 0.13181(12) 0.0548(7) Uani 1 1 d . . . H22 H 0.6188(17) 0.1034(19) 0.1417(10) 0.066 Uiso 1 1 d . . . N23 N 0.53627(15) 0.22889(15) 0.20831(9) 0.0512(5) Uani 1 1 d . . . C24 C 0.5000 0.2930(3) 0.2500 0.0466(8) Uani 1 2 d S . . O25 O 0.5000 0.39639(17) 0.2500 0.0669(7) Uani 1 2 d S . . O2A O 0.04502(15) 0.50809(15) 0.32220(9) 0.0652(6) Uani 1 1 d . . . O1A O 0.83940(17) 0.03156(14) 0.08743(10) 0.0760(6) Uani 1 1 d . . . H1A H 0.784(2) 0.088(3) 0.0795(15) 0.132(13) Uiso 1 1 d . . . H1B H 0.896(2) 0.076(3) 0.0867(14) 0.117(13) Uiso 1 1 d . . . H2A H 0.091(2) 0.535(3) 0.3493(14) 0.097(13) Uiso 1 1 d . . . H2B H 0.071(2) 0.444(3) 0.2994(14) 0.117(11) Uiso 1 1 d . . . H7 H 0.2944(18) 0.376(2) 0.1371(11) 0.070(8) Uiso 1 1 d . . . H10 H 0.3540(18) 0.369(2) 0.0593(11) 0.067(9) Uiso 1 1 d . . . H23 H 0.5230(16) 0.1518(18) 0.2072(9) 0.055(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0644(14) 0.0617(14) 0.0602(14) -0.0122(11) 0.0185(12) 0.0114(11) C2 0.0597(18) 0.0668(18) 0.0529(17) -0.0047(14) 0.0170(14) 0.0068(14) C3 0.0709(18) 0.0504(15) 0.0672(18) -0.0013(13) 0.0274(15) 0.0023(13) C4 0.0680(17) 0.0428(14) 0.0608(17) -0.0050(11) 0.0260(14) 0.0009(12) C5 0.0464(14) 0.0437(13) 0.0479(15) -0.0038(11) 0.0074(12) 0.0026(11) C6 0.0622(17) 0.0417(14) 0.0668(18) -0.0069(13) 0.0104(15) 0.0057(12) N7 0.0652(14) 0.0348(12) 0.0635(14) -0.0016(10) 0.0212(11) 0.0004(10) C8 0.0460(14) 0.0365(14) 0.0519(15) 0.0034(12) 0.0106(12) 0.0015(11) O9 0.0807(12) 0.0347(9) 0.0580(11) 0.0008(7) 0.0240(9) -0.0020(8) N10 0.0568(13) 0.0331(12) 0.0652(14) 0.0033(10) 0.0229(11) -0.0002(10) C11 0.0406(14) 0.0401(13) 0.0524(15) 0.0042(11) 0.0049(12) -0.0003(10) C12 0.0622(16) 0.0415(14) 0.0619(17) 0.0040(11) 0.0225(14) -0.0004(11) C13 0.0799(19) 0.0497(14) 0.0591(17) -0.0030(13) 0.0231(15) 0.0019(13) C14 0.073(2) 0.0699(18) 0.0567(17) 0.0033(14) 0.0229(15) 0.0033(15) N15 0.0677(15) 0.0607(14) 0.0658(15) 0.0062(11) 0.0247(12) -0.0074(11) C16 0.0564(16) 0.0455(14) 0.0643(17) 0.0048(12) 0.0130(14) -0.0046(12) N17 0.0646(14) 0.0561(14) 0.0668(15) 0.0019(11) 0.0229(12) 0.0044(11) C18 0.0630(18) 0.0639(18) 0.0600(17) 0.0042(14) 0.0162(14) -0.0006(14) C19 0.0723(18) 0.0474(14) 0.0576(17) 0.0070(12) 0.0105(15) -0.0082(13) C20 0.0652(17) 0.0415(13) 0.0580(16) -0.0016(12) 0.0113(14) -0.0007(12) C21 0.0432(15) 0.0368(12) 0.0526(15) -0.0013(11) 0.0069(12) -0.0019(10) C22 0.0538(16) 0.0434(14) 0.0693(18) 0.0012(13) 0.0167(14) 0.0013(12) N23 0.0581(14) 0.0327(11) 0.0668(15) -0.0025(10) 0.0225(11) -0.0025(9) C24 0.045(2) 0.0356(19) 0.059(2) 0.000 0.0085(18) 0.000 O25 0.094(2) 0.0332(13) 0.0816(18) 0.000 0.0383(15) 0.000 O2A 0.0773(14) 0.0450(10) 0.0749(14) -0.0100(10) 0.0171(12) 0.0071(10) O1A 0.0824(14) 0.0368(10) 0.1203(18) 0.0003(10) 0.0493(14) 0.0013(10) _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 N1 C6 1.322(3) . ? N1 C2 1.330(3) . ? C2 N1 1.330(3) 1 ? C2 C3 1.365(3) . ? C2 H2 0.99(2) . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C4 C5 1.374(3) . ? C4 H4 0.9300 . ? C5 C6 1.385(3) . ? C5 N7 1.399(3) . ? C6 N1 1.322(3) 1 ? C6 H6 0.94(2) . ? N7 C8 1.366(3) . ? N7 H7 0.86(2) . ? C8 O9 1.215(2) . ? C8 N10 1.356(3) . ? N10 C11 1.392(3) . ? N10 H10 0.82(2) . ? C11 C12 1.377(3) . ? C11 C16 1.390(3) . ? C12 C13 1.369(3) . ? C12 H12 0.9300 . ? C13 C14 1.363(3) . ? C13 H13 0.9300 . ? C14 N15 1.329(3) . ? C14 H14 0.9300 . ? N15 C16 1.325(3) . ? C16 H16 0.9300 . ? N17 C22 1.322(3) . ? N17 C18 1.333(3) . ? C18 N17 1.333(3) 1 ? C18 C19 1.364(3) . ? C18 H18 0.97(3) . ? C19 C20 1.377(3) . ? C19 H19 0.9300 . ? C20 C21 1.380(3) . ? C20 H20 0.9300 . ? C21 C22 1.391(3) . ? C21 N23 1.393(3) . ? C22 N17 1.322(3) 1 ? C22 H22 0.97(2) . ? N23 C24 1.359(2) . ? N23 H23 0.93(2) . ? C24 O25 1.220(3) . ? C24 N23 1.359(2) 2_655 ? O2A H2A 0.84(3) . ? O2A H2B 1.01(3) . ? O1A H1A 0.99(3) . ? O1A H1B 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C6 0(10) 1 . ? N1 N1 C2 0(10) 1 . ? C6 N1 C2 117.4(2) . . ? N1 C2 N1 0.0(2) 1 . ? N1 C2 C3 121.8(3) 1 . ? N1 C2 C3 121.8(3) . . ? N1 C2 H2 116.2(14) 1 . ? N1 C2 H2 116.2(14) . . ? C3 C2 H2 122.0(14) . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 116.8(2) . . ? C4 C5 N7 125.5(2) . . ? C6 C5 N7 117.7(2) . . ? N1 C6 N1 0.0(3) 1 . ? N1 C6 C5 124.9(2) 1 . ? N1 C6 C5 124.9(2) . . ? N1 C6 H6 121.1(14) 1 . ? N1 C6 H6 121.1(14) . . ? C5 C6 H6 114.1(15) . . ? C8 N7 C5 127.7(2) . . ? C8 N7 H7 114.3(17) . . ? C5 N7 H7 117.9(17) . . ? O9 C8 N10 123.5(2) . . ? O9 C8 N7 123.6(2) . . ? N10 C8 N7 112.9(2) . . ? C8 N10 C11 127.4(2) . . ? C8 N10 H10 117.9(18) . . ? C11 N10 H10 114.6(18) . . ? C12 C11 C16 116.8(2) . . ? C12 C11 N10 126.2(2) . . ? C16 C11 N10 117.0(2) . . ? C13 C12 C11 118.7(2) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? N15 C14 C13 122.7(2) . . ? N15 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? C16 N15 C14 116.8(2) . . ? N15 C16 C11 124.8(2) . . ? N15 C16 H16 117.6 . . ? C11 C16 H16 117.6 . . ? N17 N17 C22 0(10) 1 . ? N17 N17 C18 0(10) 1 . ? C22 N17 C18 117.0(2) . . ? N17 C18 N17 0.0(2) 1 . ? N17 C18 C19 122.2(3) 1 . ? N17 C18 C19 122.2(3) . . ? N17 C18 H18 115.5(14) 1 . ? N17 C18 H18 115.5(14) . . ? C19 C18 H18 122.3(14) . . ? C18 C19 C20 120.5(2) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C21 118.5(2) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C22 116.5(2) . . ? C20 C21 N23 126.5(2) . . ? C22 C21 N23 117.0(2) . . ? N17 C22 C21 125.2(2) 1 . ? N17 C22 C21 125.2(2) . . ? N17 C22 H22 117.9(14) 1 . ? N17 C22 H22 117.9(14) . . ? C21 C22 H22 116.8(14) . . ? C24 N23 C21 128.13(19) . . ? C24 N23 H23 118.7(13) . . ? C21 N23 H23 113.1(13) . . ? O25 C24 N23 123.80(13) . 2_655 ? O25 C24 N23 123.80(13) . . ? N23 C24 N23 112.4(3) 2_655 . ? H2A O2A H2B 113(3) . . ? H1A O1A H1B 101(3) . . ? 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 O1A H1A N17 0.99(3) 1.88(3) 2.834(3) 164(3) 1 O1A H1B N15 0.91(3) 1.99(3) 2.874(3) 164(3) 7_655 O2A H2A O9 0.84(3) 2.03(3) 2.858(3) 166(3) 4 O2A H2B N1 1.01(3) 1.83(3) 2.831(3) 170(2) 1 N7 H7 O1A 0.86(2) 2.28(2) 3.078(3) 154(2) 3_455 N10 H10 O1A 0.82(2) 2.04(2) 2.841(3) 164(2) 3_455 N23 H23 O2A 0.93(2) 1.97(2) 2.852(3) 157.5(19) 4_545 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 22.45 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.168 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.066