# Electronic Supplementary Material (ESI) for CrystEngComm # 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_publication_text data_INHHBAhydrateI #TrackingRef 'CIF-Srinivasulu INH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 N3 O5' _chemical_formula_weight 293.28 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.0070(14) _cell_length_b 11.224(2) _cell_length_c 16.950(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.95(3) _cell_angle_gamma 90.00 _cell_volume 1332.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4247 _cell_measurement_theta_min 1.8143 _cell_measurement_theta_max 31.0059 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9558 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10544 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3307 _reflns_number_gt 2941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0947P)^2^+0.6295P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3307 _refine_ls_number_parameters 219 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.2000 _refine_ls_wR_factor_gt 0.1913 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.201 _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 O4 O 0.0994(2) 0.35645(15) 0.62553(9) 0.0277(4) Uani 1 1 d D . . O3 O 0.1152(3) 0.31695(15) 0.99769(9) 0.0328(4) Uani 1 1 d D . . O2 O 0.1447(3) 0.12355(16) 0.96666(10) 0.0356(4) Uani 1 1 d . . . C10 C 0.1107(3) 0.3232(2) 0.70269(12) 0.0230(5) Uani 1 1 d . . . C7 C 0.1284(3) 0.2654(2) 0.86295(12) 0.0232(5) Uani 1 1 d . . . C12 C 0.0837(3) 0.3817(2) 0.83896(13) 0.0239(5) Uani 1 1 d . . . H12 H 0.0600 0.4412 0.8773 0.029 Uiso 1 1 calc R . . C9 C 0.1591(3) 0.2078(2) 0.72617(13) 0.0242(5) Uani 1 1 d . . . H9 H 0.1857 0.1488 0.6879 0.029 Uiso 1 1 calc R . . C11 C 0.0738(3) 0.4103(2) 0.75915(13) 0.0248(5) Uani 1 1 d . . . H11 H 0.0421 0.4891 0.7429 0.030 Uiso 1 1 calc R . . C8 C 0.1681(3) 0.1799(2) 0.80606(13) 0.0234(5) Uani 1 1 d . . . H8 H 0.2017 0.1013 0.8222 0.028 Uiso 1 1 calc R . . C13 C 0.1313(3) 0.2279(2) 0.94720(12) 0.0244(5) Uani 1 1 d . . . O5 O 0.1508(3) 0.45689(16) 0.43742(10) 0.0320(4) Uani 1 1 d . . . O1 O 0.0896(3) 0.02006(14) 0.39707(9) 0.0306(4) Uani 1 1 d . . . N1 N 0.1192(3) 0.24287(18) 0.14356(11) 0.0256(4) Uani 1 1 d . . . N3 N 0.1305(4) 0.16952(19) 0.52269(11) 0.0308(5) Uani 1 1 d . . . C5 C 0.1709(3) 0.2884(2) 0.28106(12) 0.0232(5) Uani 1 1 d . . . H5 H 0.2089 0.3445 0.3205 0.028 Uiso 1 1 calc R . . N2 N 0.1237(3) 0.20817(19) 0.44299(11) 0.0271(4) Uani 1 1 d . . . C1 C 0.1111(3) 0.17450(19) 0.30141(12) 0.0218(4) Uani 1 1 d . . . C6 C 0.1059(3) 0.1277(2) 0.38452(12) 0.0239(5) Uani 1 1 d . . . C3 C 0.0620(3) 0.1334(2) 0.16307(12) 0.0256(5) Uani 1 1 d . . . H3 H 0.0234 0.0797 0.1223 0.031 Uiso 1 1 calc R . . C4 C 0.1735(3) 0.3177(2) 0.20134(13) 0.0248(5) Uani 1 1 d . . . H4 H 0.2162 0.3950 0.1873 0.030 Uiso 1 1 calc R . . C2 C 0.0573(3) 0.0955(2) 0.24125(12) 0.0240(5) Uani 1 1 d . . . H2 H 0.0178 0.0168 0.2534 0.029 Uiso 1 1 calc R . . H10 H 0.121(6) 0.290(4) 1.0495(13) 0.079(12) Uiso 1 1 d D . . H14 H 0.221(5) 0.493(3) 0.465(2) 0.056(11) Uiso 1 1 d . . . H15 H 0.051(6) 0.506(4) 0.422(2) 0.064(11) Uiso 1 1 d . . . H1 H 0.131(4) 0.292(3) 0.432(2) 0.052(9) Uiso 1 1 d . . . H7 H 0.248(5) 0.127(3) 0.530(2) 0.055(10) Uiso 1 1 d . . . H6 H 0.036(5) 0.124(3) 0.5292(19) 0.042(9) Uiso 1 1 d . . . H13 H 0.119(6) 0.290(3) 0.596(2) 0.095(15) Uiso 1 1 d 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 O4 0.0390(9) 0.0273(9) 0.0167(7) 0.0020(6) 0.0020(6) 0.0007(7) O3 0.0510(11) 0.0278(9) 0.0196(8) -0.0006(6) 0.0009(7) -0.0002(7) O2 0.0550(11) 0.0284(9) 0.0233(8) 0.0042(7) -0.0005(7) 0.0029(8) C10 0.0225(10) 0.0263(11) 0.0203(10) 0.0001(8) 0.0014(8) -0.0028(8) C7 0.0264(10) 0.0238(11) 0.0195(10) 0.0005(8) 0.0005(8) -0.0013(8) C12 0.0248(10) 0.0237(11) 0.0232(10) -0.0009(8) 0.0018(8) -0.0010(8) C9 0.0263(10) 0.0256(11) 0.0206(10) -0.0020(8) 0.0006(8) -0.0014(8) C11 0.0271(11) 0.0236(11) 0.0240(10) 0.0001(8) 0.0025(8) -0.0005(8) C8 0.0237(10) 0.0231(11) 0.0234(10) 0.0017(8) 0.0005(8) -0.0006(8) C13 0.0258(11) 0.0267(12) 0.0206(10) 0.0001(8) -0.0010(8) 0.0006(9) O5 0.0411(10) 0.0254(9) 0.0291(9) -0.0039(7) -0.0035(7) -0.0008(8) O1 0.0479(10) 0.0220(8) 0.0221(8) 0.0018(6) 0.0047(7) 0.0001(7) N1 0.0272(9) 0.0298(10) 0.0197(9) -0.0004(7) 0.0012(7) 0.0031(8) N3 0.0453(13) 0.0283(11) 0.0188(9) 0.0037(7) 0.0024(8) -0.0011(10) C5 0.0234(10) 0.0238(11) 0.0224(10) -0.0020(8) 0.0016(8) 0.0002(8) N2 0.0383(11) 0.0252(10) 0.0176(9) 0.0022(7) 0.0009(7) -0.0002(8) C1 0.0226(10) 0.0236(11) 0.0193(9) 0.0003(8) 0.0016(7) 0.0024(8) C6 0.0256(10) 0.0258(11) 0.0205(10) 0.0007(8) 0.0030(8) 0.0001(8) C3 0.0281(11) 0.0272(11) 0.0213(10) -0.0026(8) -0.0016(8) 0.0015(9) C4 0.0275(11) 0.0252(11) 0.0215(10) 0.0009(8) 0.0016(8) -0.0004(8) C2 0.0270(11) 0.0233(11) 0.0216(10) -0.0007(8) 0.0016(8) 0.0009(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 O4 C10 1.360(3) . ? O4 H13 0.917(19) . ? O3 C13 1.323(3) . ? O3 H10 0.928(19) . ? O2 C13 1.219(3) . ? C10 C9 1.393(3) . ? C10 C11 1.399(3) . ? C7 C8 1.396(3) . ? C7 C12 1.399(3) . ? C7 C13 1.488(3) . ? C12 C11 1.390(3) . ? C12 H12 0.9500 . ? C9 C8 1.389(3) . ? C9 H9 0.9500 . ? C11 H11 0.9500 . ? C8 H8 0.9500 . ? O5 H14 0.78(4) . ? O5 H15 0.92(4) . ? O1 C6 1.233(3) . ? N1 C4 1.336(3) . ? N1 C3 1.338(3) . ? N3 N2 1.418(3) . ? N3 H7 0.96(4) . ? N3 H6 0.85(3) . ? C5 C4 1.392(3) . ? C5 C1 1.392(3) . ? C5 H5 0.9500 . ? N2 C6 1.344(3) . ? N2 H1 0.96(4) . ? C1 C2 1.394(3) . ? C1 C6 1.505(3) . ? C3 C2 1.393(3) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C2 H2 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 C10 O4 H13 107(3) . . ? C13 O3 H10 111(3) . . ? O4 C10 C9 122.4(2) . . ? O4 C10 C11 117.4(2) . . ? C9 C10 C11 120.2(2) . . ? C8 C7 C12 119.27(19) . . ? C8 C7 C13 118.1(2) . . ? C12 C7 C13 122.6(2) . . ? C11 C12 C7 120.1(2) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C8 C9 C10 119.4(2) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? O2 C13 O3 123.9(2) . . ? O2 C13 C7 122.0(2) . . ? O3 C13 C7 114.1(2) . . ? H14 O5 H15 108(4) . . ? C4 N1 C3 118.49(19) . . ? N2 N3 H7 106(2) . . ? N2 N3 H6 108(2) . . ? H7 N3 H6 111(3) . . ? C4 C5 C1 118.2(2) . . ? C4 C5 H5 120.9 . . ? C1 C5 H5 120.9 . . ? C6 N2 N3 119.8(2) . . ? C6 N2 H1 121(2) . . ? N3 N2 H1 119(2) . . ? C5 C1 C2 118.63(19) . . ? C5 C1 C6 124.71(19) . . ? C2 C1 C6 116.63(19) . . ? O1 C6 N2 122.6(2) . . ? O1 C6 C1 120.6(2) . . ? N2 C6 C1 116.81(19) . . ? N1 C3 C2 122.2(2) . . ? N1 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? N1 C4 C5 123.4(2) . . ? N1 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.426 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 935247' ####################################################################### # # 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_publication_text #====END data_INHHBAhydrateII #TrackingRef 'CIF-Srinivasulu INH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 N3 O5' _chemical_formula_weight 293.28 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8143(14) _cell_length_b 22.419(5) _cell_length_c 8.8759(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.85(3) _cell_angle_gamma 90.00 _cell_volume 1327.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4302 _cell_measurement_theta_min 3.0546 _cell_measurement_theta_max 31.0602 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9752 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10379 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5747 _reflns_number_gt 5323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0744P)^2^+0.3823P] 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 5747 _refine_ls_number_parameters 435 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 O3A O 0.8232(3) 0.20930(8) 0.0945(2) 0.0268(4) Uani 1 1 d D . . O2A O 0.8158(3) 0.10960(8) 0.0914(2) 0.0273(4) Uani 1 1 d . . . O1A O 0.6639(3) 0.13645(8) 0.6845(2) 0.0292(4) Uani 1 1 d . . . C1A C 0.4329(3) 0.19359(11) 0.7944(2) 0.0213(4) Uani 1 1 d . . . O4A O 0.1116(3) 0.17598(9) 0.4384(2) 0.0323(4) Uani 1 1 d . . . C7A C 0.5856(3) 0.16244(11) 0.2132(3) 0.0211(4) Uani 1 1 d . . . N1A N 0.1121(3) 0.19911(10) 0.9437(2) 0.0238(4) Uani 1 1 d . . . C9A C 0.3320(4) 0.11405(12) 0.3256(3) 0.0253(5) Uani 1 1 d . . . H9A H 0.2683 0.0787 0.3502 0.030 Uiso 1 1 calc R . . C5A C 0.3678(3) 0.24794(11) 0.8397(3) 0.0224(4) Uani 1 1 d . . . H5A H 0.4317 0.2840 0.8204 0.027 Uiso 1 1 calc R . . C11A C 0.3593(4) 0.22163(12) 0.3290(3) 0.0268(5) Uani 1 1 d . . . H11A H 0.3145 0.2595 0.3564 0.032 Uiso 1 1 calc R . . C12A C 0.5177(3) 0.21772(11) 0.2532(3) 0.0239(5) Uani 1 1 d . . . H12A H 0.5806 0.2531 0.2282 0.029 Uiso 1 1 calc R . . C4A C 0.2079(4) 0.24864(11) 0.9137(3) 0.0224(5) Uani 1 1 d . . . H4A H 0.1637 0.2860 0.9448 0.027 Uiso 1 1 calc R . . N2A N 0.6889(3) 0.23641(10) 0.6743(2) 0.0244(4) Uani 1 1 d . . . C10A C 0.2661(4) 0.16948(12) 0.3648(3) 0.0244(5) Uani 1 1 d . . . C8A C 0.4915(4) 0.11049(11) 0.2502(3) 0.0236(5) Uani 1 1 d . . . H8A H 0.5369 0.0726 0.2237 0.028 Uiso 1 1 calc R . . C3A C 0.1753(4) 0.14684(12) 0.9007(3) 0.0266(5) Uani 1 1 d . . . H3A H 0.1096 0.1115 0.9229 0.032 Uiso 1 1 calc R . . C13A C 0.7516(3) 0.15749(11) 0.1286(3) 0.0218(4) Uani 1 1 d . . . N3A N 0.8479(3) 0.23426(10) 0.5939(2) 0.0253(4) Uani 1 1 d . . . C2A C 0.3346(4) 0.14188(11) 0.8244(3) 0.0251(5) Uani 1 1 d . . . H2A H 0.3749 0.1040 0.7936 0.030 Uiso 1 1 calc R . . O5A O 0.9568(3) 0.08224(9) 0.5438(2) 0.0323(4) Uani 1 1 d . . . C6A C 0.6049(4) 0.18616(11) 0.7123(3) 0.0225(5) Uani 1 1 d . . . O3 O 0.6440(3) 0.45827(8) 0.6882(2) 0.0303(4) Uani 1 1 d D . . O1 O 0.2399(3) 0.38801(8) -0.1472(2) 0.0267(4) Uani 1 1 d . . . O2 O 0.6336(3) 0.35897(8) 0.69204(19) 0.0280(4) Uani 1 1 d . . . C1 C 0.3250(3) 0.44398(11) 0.0853(3) 0.0222(5) Uani 1 1 d . . . C7 C 0.7541(3) 0.41077(11) 0.9273(3) 0.0214(4) Uani 1 1 d . . . N1 N 0.4756(3) 0.44839(10) 0.4013(2) 0.0241(4) Uani 1 1 d . . . C12 C 0.7807(4) 0.46561(11) 1.0024(3) 0.0233(5) Uani 1 1 d . . . H12 H 0.7488 0.5012 0.9444 0.028 Uiso 1 1 calc R . . C9 C 0.8785(4) 0.36165(12) 1.1713(3) 0.0248(5) Uani 1 1 d . . . H9 H 0.9131 0.3261 1.2290 0.030 Uiso 1 1 calc R . . C10 C 0.9014(3) 0.41695(12) 1.2440(3) 0.0249(5) Uani 1 1 d . . . N2 N 0.1986(3) 0.48807(10) -0.1656(2) 0.0239(4) Uani 1 1 d . . . C8 C 0.8044(3) 0.35885(11) 1.0131(3) 0.0225(4) Uani 1 1 d . . . H8 H 0.7879 0.3212 0.9631 0.027 Uiso 1 1 calc R . . O4 O 0.9714(3) 0.42335(9) 1.3976(2) 0.0330(4) Uani 1 1 d . . . C13 C 0.6717(4) 0.40652(11) 0.7590(3) 0.0229(5) Uani 1 1 d . . . C2 C 0.3814(4) 0.39226(11) 0.1695(3) 0.0239(5) Uani 1 1 d . . . H2 H 0.3695 0.3546 0.1195 0.029 Uiso 1 1 calc R . . C6 C 0.2500(3) 0.43759(11) -0.0859(3) 0.0219(5) Uani 1 1 d . . . C5 C 0.3431(4) 0.49801(11) 0.1637(3) 0.0232(5) Uani 1 1 d . . . H5 H 0.3031 0.5342 0.1104 0.028 Uiso 1 1 calc R . . N3 N 0.1322(3) 0.48611(11) -0.3283(2) 0.0288(5) Uani 1 1 d . . . C4 C 0.4207(4) 0.49838(11) 0.3212(3) 0.0252(5) Uani 1 1 d . . . H4 H 0.4353 0.5355 0.3740 0.030 Uiso 1 1 calc R . . C11 C 0.8527(4) 0.46934(11) 1.1598(3) 0.0255(5) Uani 1 1 d . . . H11 H 0.8687 0.5070 1.2097 0.031 Uiso 1 1 calc R . . C3 C 0.4553(4) 0.39610(11) 0.3270(3) 0.0257(5) Uani 1 1 d . . . H3 H 0.4925 0.3605 0.3839 0.031 Uiso 1 1 calc R . . O5 O 0.1070(3) 0.33118(9) 0.5619(2) 0.0327(4) Uani 1 1 d . . . H1 H 0.201(4) 0.5236(14) -0.120(3) 0.017(6) Uiso 1 1 d . . . H10A H 0.926(6) 0.203(2) 0.043(5) 0.078(14) Uiso 1 1 d D . . H7 H -0.001(5) 0.4683(14) -0.357(4) 0.032(8) Uiso 1 1 d . . . H13 H 0.987(7) 0.387(2) 1.448(5) 0.065(13) Uiso 1 1 d . . . H6A H 0.940(5) 0.2038(15) 0.642(4) 0.032(8) Uiso 1 1 d . . . H7A H 0.805(4) 0.2197(12) 0.496(3) 0.019(6) Uiso 1 1 d . . . H6 H 0.215(6) 0.4594(19) -0.372(4) 0.052(10) Uiso 1 1 d . . . H14A H 0.907(7) 0.053(2) 0.461(6) 0.084(15) Uiso 1 1 d . . . H10 H 0.586(7) 0.453(3) 0.586(3) 0.088(16) Uiso 1 1 d D . . H15A H 0.853(6) 0.0924(19) 0.579(5) 0.057(12) Uiso 1 1 d . . . H13A H 0.071(6) 0.1394(17) 0.464(4) 0.048(11) Uiso 1 1 d . . . H1A H 0.643(4) 0.2727(15) 0.692(3) 0.025(7) Uiso 1 1 d . . . H15 H 0.157(8) 0.349(3) 0.659(7) 0.100(18) Uiso 1 1 d . . . H14 H 0.021(6) 0.3006(19) 0.575(4) 0.051(11) 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 O3A 0.0261(8) 0.0225(9) 0.0346(9) 0.0018(7) 0.0130(7) 0.0003(7) O2A 0.0303(9) 0.0222(9) 0.0324(9) -0.0021(7) 0.0130(7) -0.0008(7) O1A 0.0335(9) 0.0191(9) 0.0379(10) -0.0032(7) 0.0145(8) 0.0004(7) C1A 0.0205(10) 0.0223(12) 0.0209(10) -0.0006(9) 0.0043(8) 0.0007(9) O4A 0.0334(10) 0.0324(10) 0.0360(10) 0.0011(8) 0.0183(8) 0.0016(8) C7A 0.0215(10) 0.0209(12) 0.0207(10) 0.0003(8) 0.0039(8) 0.0004(8) N1A 0.0210(9) 0.0264(11) 0.0239(9) 0.0028(8) 0.0045(7) 0.0000(8) C9A 0.0249(11) 0.0264(13) 0.0263(11) 0.0007(9) 0.0095(9) -0.0009(10) C5A 0.0212(10) 0.0220(12) 0.0237(10) 0.0018(9) 0.0039(8) -0.0016(9) C11A 0.0309(12) 0.0221(13) 0.0283(12) -0.0007(9) 0.0081(10) 0.0046(10) C12A 0.0258(11) 0.0209(12) 0.0249(11) 0.0018(9) 0.0051(9) -0.0009(9) C4A 0.0250(11) 0.0203(12) 0.0214(10) -0.0013(8) 0.0037(8) 0.0019(9) N2A 0.0256(10) 0.0221(11) 0.0281(10) -0.0016(8) 0.0115(8) 0.0009(8) C10A 0.0236(10) 0.0278(13) 0.0226(11) -0.0013(9) 0.0066(9) 0.0005(10) C8A 0.0256(11) 0.0218(12) 0.0245(11) -0.0004(9) 0.0078(9) 0.0015(9) C3A 0.0280(11) 0.0216(12) 0.0302(12) 0.0031(9) 0.0057(9) -0.0014(10) C13A 0.0205(10) 0.0214(12) 0.0238(10) 0.0000(9) 0.0053(8) -0.0002(9) N3A 0.0252(10) 0.0266(11) 0.0262(10) -0.0026(8) 0.0099(8) 0.0009(8) C2A 0.0280(11) 0.0189(12) 0.0287(12) 0.0019(9) 0.0065(9) 0.0022(9) O5A 0.0308(9) 0.0326(11) 0.0362(10) -0.0048(8) 0.0127(8) -0.0034(8) C6A 0.0233(10) 0.0220(12) 0.0222(10) -0.0006(9) 0.0045(8) -0.0001(9) O3 0.0463(11) 0.0199(9) 0.0221(8) 0.0011(7) 0.0013(8) -0.0001(8) O1 0.0325(9) 0.0213(9) 0.0252(8) -0.0008(7) 0.0033(7) -0.0004(7) O2 0.0401(10) 0.0191(9) 0.0242(8) -0.0001(7) 0.0055(7) 0.0002(8) C1 0.0208(10) 0.0225(12) 0.0244(11) 0.0020(9) 0.0072(8) 0.0001(9) C7 0.0209(10) 0.0223(12) 0.0219(10) -0.0016(9) 0.0068(8) -0.0004(8) N1 0.0267(9) 0.0229(10) 0.0232(9) 0.0006(8) 0.0065(7) 0.0006(8) C12 0.0236(11) 0.0212(13) 0.0261(11) 0.0005(9) 0.0071(9) 0.0017(9) C9 0.0242(10) 0.0249(12) 0.0253(11) 0.0040(9) 0.0052(9) 0.0015(9) C10 0.0197(10) 0.0294(13) 0.0258(11) -0.0016(10) 0.0047(8) -0.0013(9) N2 0.0286(10) 0.0223(11) 0.0203(9) 0.0017(8) 0.0040(8) -0.0011(8) C8 0.0265(11) 0.0190(11) 0.0229(11) -0.0030(8) 0.0070(9) -0.0008(9) O4 0.0415(10) 0.0292(10) 0.0248(9) 0.0009(8) -0.0010(8) -0.0006(8) C13 0.0252(11) 0.0234(12) 0.0210(10) -0.0003(9) 0.0069(8) 0.0015(9) C2 0.0271(11) 0.0175(11) 0.0269(11) -0.0020(9) 0.0049(9) -0.0022(9) C6 0.0189(9) 0.0240(13) 0.0236(11) -0.0013(9) 0.0059(8) -0.0017(9) C5 0.0239(10) 0.0206(12) 0.0256(11) 0.0024(9) 0.0060(9) 0.0010(9) N3 0.0337(11) 0.0290(12) 0.0220(10) 0.0006(8) 0.0017(8) -0.0002(9) C4 0.0293(11) 0.0201(12) 0.0278(12) -0.0036(9) 0.0091(9) -0.0001(9) C11 0.0229(11) 0.0246(13) 0.0299(12) -0.0059(10) 0.0072(9) -0.0016(9) C3 0.0292(12) 0.0216(12) 0.0260(11) 0.0030(9) 0.0051(9) 0.0013(9) O5 0.0391(10) 0.0293(10) 0.0279(9) 0.0051(8) 0.0029(8) -0.0068(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 O3A C13A 1.319(3) . ? O3A H10A 0.922(19) . ? O2A C13A 1.230(3) . ? O1A C6A 1.227(3) . ? C1A C5A 1.384(3) . ? C1A C2A 1.392(3) . ? C1A C6A 1.511(3) . ? O4A C10A 1.356(3) . ? O4A H13A 0.91(4) . ? C7A C12A 1.394(3) . ? C7A C8A 1.401(3) . ? C7A C13A 1.485(3) . ? N1A C3A 1.331(3) . ? N1A C4A 1.342(3) . ? C9A C10A 1.390(4) . ? C9A C8A 1.391(3) . ? C9A H9A 0.9500 . ? C5A C4A 1.383(3) . ? C5A H5A 0.9500 . ? C11A C12A 1.387(3) . ? C11A C10A 1.398(3) . ? C11A H11A 0.9500 . ? C12A H12A 0.9500 . ? C4A H4A 0.9500 . ? N2A C6A 1.338(3) . ? N2A N3A 1.415(3) . ? N2A H1A 0.90(3) . ? C8A H8A 0.9500 . ? C3A C2A 1.397(3) . ? C3A H3A 0.9500 . ? N3A H6A 0.97(3) . ? N3A H7A 0.92(3) . ? C2A H2A 0.9500 . ? O5A H14A 0.99(5) . ? O5A H15A 0.86(4) . ? O3 C13 1.314(3) . ? O3 H10 0.919(19) . ? O1 C6 1.233(3) . ? O2 C13 1.222(3) . ? C1 C5 1.390(4) . ? C1 C2 1.390(3) . ? C1 C6 1.507(3) . ? C7 C12 1.392(3) . ? C7 C8 1.394(3) . ? C7 C13 1.487(3) . ? N1 C3 1.338(3) . ? N1 C4 1.339(3) . ? C12 C11 1.385(3) . ? C12 H12 0.9500 . ? C9 C10 1.392(4) . ? C9 C8 1.393(3) . ? C9 H9 0.9500 . ? C10 O4 1.356(3) . ? C10 C11 1.395(4) . ? N2 C6 1.343(3) . ? N2 N3 1.422(3) . ? N2 H1 0.89(3) . ? C8 H8 0.9500 . ? O4 H13 0.93(5) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C5 C4 1.389(3) . ? C5 H5 0.9500 . ? N3 H7 0.98(3) . ? N3 H6 0.96(4) . ? C4 H4 0.9500 . ? C11 H11 0.9500 . ? C3 H3 0.9500 . ? O5 H15 0.95(6) . ? O5 H14 0.92(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 C13A O3A H10A 109(3) . . ? C5A C1A C2A 118.8(2) . . ? C5A C1A C6A 124.3(2) . . ? C2A C1A C6A 116.9(2) . . ? C10A O4A H13A 109(2) . . ? C12A C7A C8A 119.2(2) . . ? C12A C7A C13A 121.5(2) . . ? C8A C7A C13A 119.3(2) . . ? C3A N1A C4A 118.22(19) . . ? C10A C9A C8A 119.8(2) . . ? C10A C9A H9A 120.1 . . ? C8A C9A H9A 120.1 . . ? C4A C5A C1A 118.6(2) . . ? C4A C5A H5A 120.7 . . ? C1A C5A H5A 120.7 . . ? C12A C11A C10A 119.5(2) . . ? C12A C11A H11A 120.2 . . ? C10A C11A H11A 120.2 . . ? C11A C12A C7A 120.8(2) . . ? C11A C12A H12A 119.6 . . ? C7A C12A H12A 119.6 . . ? N1A C4A C5A 123.2(2) . . ? N1A C4A H4A 118.4 . . ? C5A C4A H4A 118.4 . . ? C6A N2A N3A 120.7(2) . . ? C6A N2A H1A 123(2) . . ? N3A N2A H1A 117(2) . . ? O4A C10A C9A 122.7(2) . . ? O4A C10A C11A 117.0(2) . . ? C9A C10A C11A 120.4(2) . . ? C9A C8A C7A 120.4(2) . . ? C9A C8A H8A 119.8 . . ? C7A C8A H8A 119.8 . . ? N1A C3A C2A 122.6(2) . . ? N1A C3A H3A 118.7 . . ? C2A C3A H3A 118.7 . . ? O2A C13A O3A 122.6(2) . . ? O2A C13A C7A 123.4(2) . . ? O3A C13A C7A 114.0(2) . . ? N2A N3A H6A 107.2(18) . . ? N2A N3A H7A 111.1(17) . . ? H6A N3A H7A 103(3) . . ? C1A C2A C3A 118.6(2) . . ? C1A C2A H2A 120.7 . . ? C3A C2A H2A 120.7 . . ? H14A O5A H15A 105(4) . . ? O1A C6A N2A 122.6(2) . . ? O1A C6A C1A 121.0(2) . . ? N2A C6A C1A 116.3(2) . . ? C13 O3 H10 110(4) . . ? C5 C1 C2 118.1(2) . . ? C5 C1 C6 124.4(2) . . ? C2 C1 C6 117.5(2) . . ? C12 C7 C8 118.9(2) . . ? C12 C7 C13 121.5(2) . . ? C8 C7 C13 119.6(2) . . ? C3 N1 C4 118.9(2) . . ? C11 C12 C7 121.4(2) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? C10 C9 C8 119.4(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O4 C10 C9 122.9(2) . . ? O4 C10 C11 116.5(2) . . ? C9 C10 C11 120.6(2) . . ? C6 N2 N3 120.2(2) . . ? C6 N2 H1 122.2(17) . . ? N3 N2 H1 117.5(18) . . ? C9 C8 C7 120.7(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 O4 H13 112(3) . . ? O2 C13 O3 122.8(2) . . ? O2 C13 C7 122.9(2) . . ? O3 C13 C7 114.3(2) . . ? C3 C2 C1 119.5(2) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? O1 C6 N2 122.8(2) . . ? O1 C6 C1 120.5(2) . . ? N2 C6 C1 116.7(2) . . ? C4 C5 C1 119.0(2) . . ? C4 C5 H5 120.5 . . ? C1 C5 H5 120.5 . . ? N2 N3 H7 111.4(19) . . ? N2 N3 H6 110(2) . . ? H7 N3 H6 103(3) . . ? N1 C4 C5 122.4(2) . . ? N1 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C12 C11 C10 119.1(2) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? N1 C3 C2 122.0(2) . . ? N1 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? H15 O5 H14 108(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.310 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 935248' ####################################################################### # # 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_publication_text #====END data_INHFAI #TrackingRef 'CIF-Srinivasulu INH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N6 O6' _chemical_formula_weight 390.36 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8906(16) _cell_length_b 8.7030(17) _cell_length_c 12.517(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.84(3) _cell_angle_gamma 90.00 _cell_volume 851.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1968 _cell_measurement_theta_min 2.8595 _cell_measurement_theta_max 30.9019 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9494 _exptl_absorpt_correction_T_max 0.9742 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6538 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2113 _reflns_number_gt 2014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0560P)^2^+0.3743P] 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 2113 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 O3 O 0.12740(13) 0.31662(11) 1.02198(8) 0.0240(3) Uani 1 1 d . . . O1 O 0.64440(15) 0.84774(12) 0.72167(9) 0.0288(3) Uani 1 1 d . . . O2 O 0.23971(14) 0.14120(12) 0.92193(9) 0.0261(3) Uani 1 1 d . . . N1 N 0.30191(15) 0.51372(13) 0.93761(9) 0.0209(3) Uani 1 1 d . . . N3 N 0.53944(17) 1.14890(14) 0.74586(11) 0.0245(3) Uani 1 1 d . . . C7 C 0.14022(17) 0.17930(15) 0.98499(11) 0.0196(3) Uani 1 1 d . . . N2 N 0.49293(15) 1.02083(13) 0.80547(10) 0.0213(3) Uani 1 1 d . . . C3 C 0.29878(18) 0.65607(16) 0.97828(11) 0.0211(3) Uani 1 1 d . . . H3 H 0.2410 0.6736 1.0390 0.025 Uiso 1 1 calc R . . C2 C 0.37769(17) 0.77826(16) 0.93398(11) 0.0203(3) Uani 1 1 d . . . H2 H 0.3740 0.8785 0.9637 0.024 Uiso 1 1 calc R . . C6 C 0.54292(17) 0.87743(16) 0.78549(11) 0.0201(3) Uani 1 1 d . . . C5 C 0.47063(18) 0.60223(16) 0.80612(11) 0.0213(3) Uani 1 1 d . . . H5 H 0.5321 0.5805 0.7477 0.026 Uiso 1 1 calc R . . C1 C 0.46268(17) 0.75155(15) 0.84489(10) 0.0192(3) Uani 1 1 d . . . C8 C 0.01966(17) 0.06659(15) 1.02480(11) 0.0205(3) Uani 1 1 d . . . H8 H -0.0304 0.0910 1.0875 0.025 Uiso 1 1 calc R . . C4 C 0.38758(18) 0.48527(16) 0.85389(11) 0.0223(3) Uani 1 1 d . . . H4 H 0.3913 0.3834 0.8270 0.027 Uiso 1 1 calc R . . H1 H 0.403(3) 1.038(2) 0.8470(16) 0.036(5) Uiso 1 1 d . . . H7 H 0.645(3) 1.179(2) 0.7729(17) 0.040(6) Uiso 1 1 d . . . H6 H 0.543(3) 1.120(2) 0.6750(18) 0.041(5) Uiso 1 1 d . . . H9 H 0.218(3) 0.406(3) 0.9785(19) 0.063(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 O3 0.0288(5) 0.0163(5) 0.0292(5) -0.0037(4) 0.0126(4) -0.0046(4) O1 0.0322(6) 0.0235(5) 0.0346(6) 0.0046(4) 0.0191(5) 0.0054(4) O2 0.0265(5) 0.0213(5) 0.0334(6) -0.0037(4) 0.0153(4) -0.0024(4) N1 0.0203(6) 0.0178(6) 0.0247(6) 0.0009(4) 0.0036(4) -0.0015(4) N3 0.0273(7) 0.0184(6) 0.0300(6) 0.0047(5) 0.0120(5) -0.0015(5) C7 0.0194(6) 0.0182(6) 0.0219(6) 0.0005(5) 0.0050(5) -0.0010(5) N2 0.0237(6) 0.0168(5) 0.0253(6) 0.0023(4) 0.0105(5) -0.0010(4) C3 0.0207(6) 0.0194(6) 0.0241(6) 0.0013(5) 0.0062(5) 0.0000(5) C2 0.0211(6) 0.0177(6) 0.0229(6) 0.0003(5) 0.0066(5) -0.0006(5) C6 0.0196(6) 0.0197(6) 0.0219(6) 0.0013(5) 0.0055(5) 0.0007(5) C5 0.0220(6) 0.0199(7) 0.0224(6) -0.0012(5) 0.0043(5) 0.0014(5) C1 0.0171(6) 0.0191(6) 0.0213(6) 0.0019(5) 0.0026(5) 0.0007(5) C8 0.0206(6) 0.0180(6) 0.0243(6) 0.0003(5) 0.0078(5) -0.0012(5) C4 0.0233(7) 0.0181(6) 0.0254(7) 0.0000(5) 0.0028(5) -0.0001(5) _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 O3 C7 1.2905(16) . ? O3 H9 1.23(3) . ? O1 C6 1.2332(17) . ? O2 C7 1.2323(17) . ? N1 C3 1.3409(18) . ? N1 C4 1.3452(18) . ? N1 H9 1.29(3) . ? N3 N2 1.4173(16) . ? N3 H7 0.89(2) . ? N3 H6 0.93(2) . ? C7 C8 1.4983(18) . ? N2 C6 1.3426(18) . ? N2 H1 0.95(2) . ? C3 C2 1.3858(19) . ? C3 H3 0.9500 . ? C2 C1 1.3969(19) . ? C2 H2 0.9500 . ? C6 C1 1.5107(18) . ? C5 C4 1.389(2) . ? C5 C1 1.3916(19) . ? C5 H5 0.9500 . ? C8 C8 1.331(3) 3_557 ? C8 H8 0.9500 . ? C4 H4 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 C7 O3 H9 110.3(11) . . ? C3 N1 C4 120.21(12) . . ? C3 N1 H9 118.9(11) . . ? C4 N1 H9 120.9(11) . . ? N2 N3 H7 109.0(13) . . ? N2 N3 H6 109.5(13) . . ? H7 N3 H6 107.1(19) . . ? O2 C7 O3 124.54(13) . . ? O2 C7 C8 121.72(12) . . ? O3 C7 C8 113.73(12) . . ? C6 N2 N3 121.95(12) . . ? C6 N2 H1 120.7(13) . . ? N3 N2 H1 115.6(13) . . ? N1 C3 C2 121.63(13) . . ? N1 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C2 C1 118.86(13) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? O1 C6 N2 123.27(13) . . ? O1 C6 C1 121.31(13) . . ? N2 C6 C1 115.40(12) . . ? C4 C5 C1 119.20(13) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? C5 C1 C2 118.89(12) . . ? C5 C1 C6 117.63(12) . . ? C2 C1 C6 123.46(12) . . ? C8 C8 C7 122.21(16) 3_557 . ? C8 C8 H8 118.9 3_557 . ? C7 C8 H8 118.9 . . ? N1 C4 C5 121.13(13) . . ? N1 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.263 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 935249' ####################################################################### # # 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_publication_text #====END data_INHFAI_I #TrackingRef 'CIF-Srinivasulu INH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N6 O6' _chemical_formula_weight 390.36 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.7036(7) _cell_length_b 7.8401(16) _cell_length_c 29.573(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.63(3) _cell_angle_gamma 90.00 _cell_volume 858.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1961 _cell_measurement_theta_min 2.5979 _cell_measurement_theta_max 30.9137 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9498 _exptl_absorpt_correction_T_max 0.9744 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6384 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2095 _reflns_number_gt 1881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1181P)^2^+0.2933P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2095 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.2067 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 O3 O 1.2223(4) 0.26365(18) 0.03442(5) 0.0283(4) Uani 1 1 d . . . N2 N 0.4364(5) 0.9616(2) 0.17626(6) 0.0240(4) Uani 1 1 d . . . O2 O 1.1869(4) 0.06940(19) 0.08927(5) 0.0295(4) Uani 1 1 d . . . N1 N 0.9573(4) 0.4574(2) 0.09441(6) 0.0247(4) Uani 1 1 d . . . O1 O 0.6957(4) 0.80498(19) 0.23190(5) 0.0290(4) Uani 1 1 d . . . C1 C 0.7266(5) 0.6969(2) 0.15660(6) 0.0210(4) Uani 1 1 d . . . C5 C 0.7448(5) 0.7367(2) 0.11064(7) 0.0238(4) Uani 1 1 d . . . H5 H 0.6788 0.8469 0.1001 0.029 Uiso 1 1 calc R . . C2 C 0.8240(5) 0.5339(2) 0.17052(7) 0.0243(4) Uani 1 1 d . . . H2 H 0.8125 0.5030 0.2015 0.029 Uiso 1 1 calc R . . C8 C 1.4121(5) -0.0194(2) 0.01883(6) 0.0246(4) Uani 1 1 d . . . H8 H 1.3787 -0.1364 0.0260 0.030 Uiso 1 1 calc R . . C4 C 0.8605(5) 0.6130(3) 0.08064(7) 0.0258(4) Uani 1 1 d . . . H4 H 0.8713 0.6398 0.0494 0.031 Uiso 1 1 calc R . . N3 N 0.3091(5) 1.0926(2) 0.20493(6) 0.0279(4) Uani 1 1 d . . . C6 C 0.6176(5) 0.8262(2) 0.19176(6) 0.0223(4) Uani 1 1 d . . . C3 C 0.9388(5) 0.4165(2) 0.13842(7) 0.0250(4) Uani 1 1 d . . . H3 H 1.0056 0.3049 0.1479 0.030 Uiso 1 1 calc R . . C7 C 1.2650(5) 0.1109(3) 0.05028(7) 0.0241(4) Uani 1 1 d . . . H1 H 0.373(7) 0.974(3) 0.1462(9) 0.027(6) Uiso 1 1 d . . . H6 H 0.495(7) 1.143(3) 0.2190(9) 0.030(6) Uiso 1 1 d . . . H7 H 0.187(11) 1.033(5) 0.2278(13) 0.069(11) Uiso 1 1 d . . . H9 H 1.093(10) 0.350(5) 0.0644(12) 0.064(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 O3 0.0372(8) 0.0257(7) 0.0221(7) -0.0005(5) 0.0036(6) 0.0044(6) N2 0.0300(9) 0.0211(8) 0.0210(8) -0.0028(6) -0.0019(6) 0.0039(6) O2 0.0364(8) 0.0302(8) 0.0219(8) 0.0000(6) 0.0009(6) 0.0066(6) N1 0.0264(8) 0.0238(8) 0.0239(8) -0.0029(6) -0.0001(6) 0.0025(6) O1 0.0363(8) 0.0305(8) 0.0200(7) -0.0007(6) -0.0027(6) 0.0055(6) C1 0.0211(8) 0.0209(9) 0.0212(9) -0.0027(7) 0.0005(6) 0.0015(6) C5 0.0284(9) 0.0220(9) 0.0210(9) -0.0006(7) 0.0003(7) 0.0037(7) C2 0.0266(10) 0.0239(9) 0.0225(9) 0.0002(7) -0.0002(7) 0.0012(7) C8 0.0278(10) 0.0222(9) 0.0238(9) -0.0026(7) -0.0023(7) 0.0043(7) C4 0.0281(9) 0.0267(9) 0.0224(9) -0.0001(7) 0.0003(7) 0.0035(7) N3 0.0323(9) 0.0262(9) 0.0253(9) -0.0058(7) -0.0026(7) 0.0059(7) C6 0.0210(9) 0.0226(9) 0.0232(9) -0.0006(7) 0.0003(6) -0.0004(6) C3 0.0268(9) 0.0241(9) 0.0242(10) 0.0000(7) -0.0008(7) 0.0019(7) C7 0.0235(9) 0.0262(9) 0.0227(9) -0.0024(7) -0.0021(7) 0.0020(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 O3 C7 1.295(2) . ? O3 H9 1.22(4) . ? N2 C6 1.335(2) . ? N2 N3 1.416(2) . ? N2 H1 0.92(3) . ? O2 C7 1.235(2) . ? N1 C4 1.334(3) . ? N1 C3 1.343(3) . ? N1 H9 1.33(4) . ? O1 C6 1.230(2) . ? C1 C2 1.389(3) . ? C1 C5 1.397(3) . ? C1 C6 1.510(3) . ? C5 C4 1.385(3) . ? C5 H5 0.9500 . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C8 C8 1.331(4) 3_855 ? C8 C7 1.489(3) . ? C8 H8 0.9500 . ? C4 H4 0.9500 . ? N3 H6 0.89(3) . ? N3 H7 0.95(4) . ? C3 H3 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 C7 O3 H9 107.2(17) . . ? C6 N2 N3 122.74(16) . . ? C6 N2 H1 122.5(16) . . ? N3 N2 H1 114.6(16) . . ? C4 N1 C3 119.87(17) . . ? C4 N1 H9 118.7(16) . . ? C3 N1 H9 121.3(16) . . ? C2 C1 C5 118.60(16) . . ? C2 C1 C6 118.94(17) . . ? C5 C1 C6 122.42(16) . . ? C4 C5 C1 119.05(17) . . ? C4 C5 H5 120.5 . . ? C1 C5 H5 120.5 . . ? C1 C2 C3 119.11(17) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C8 C8 C7 123.5(2) 3_855 . ? C8 C8 H8 118.3 3_855 . ? C7 C8 H8 118.3 . . ? N1 C4 C5 121.91(18) . . ? N1 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? N2 N3 H6 109.8(17) . . ? N2 N3 H7 103(2) . . ? H6 N3 H7 105(3) . . ? O1 C6 N2 123.45(17) . . ? O1 C6 C1 120.79(17) . . ? N2 C6 C1 115.77(17) . . ? N1 C3 C2 121.47(18) . . ? N1 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? O2 C7 O3 123.57(18) . . ? O2 C7 C8 119.55(18) . . ? O3 C7 C8 116.88(17) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.461 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 935250' ####################################################################### # # 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_publication_text #====END data_INHNAFA #TrackingRef 'CIF-Srinivasulu INH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N5 O6' _chemical_formula_weight 375.35 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.0595(10) _cell_length_b 17.246(3) _cell_length_c 19.056(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.25(3) _cell_angle_gamma 90.00 _cell_volume 1649.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5411 _cell_measurement_theta_min 2.1547 _cell_measurement_theta_max 31.2504 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9498 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22825 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4045 _reflns_number_gt 3988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0783P)^2^+0.8775P] 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 4045 _refine_ls_number_parameters 272 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1548 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.185 _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 O3 O -0.1169(3) 0.83655(7) 0.12857(7) 0.0291(3) Uani 1 1 d . . . O6 O 0.6865(2) 0.96741(7) 0.26194(7) 0.0265(3) Uani 1 1 d D . . O4 O -0.2218(3) 0.92521(8) 0.04346(7) 0.0283(3) Uani 1 1 d D . . O5 O 0.5167(3) 1.06496(7) 0.19254(7) 0.0289(3) Uani 1 1 d . . . C16 C 0.5098(3) 0.99797(10) 0.21369(9) 0.0223(3) Uani 1 1 d . . . C13 C -0.0743(3) 0.89777(9) 0.09953(9) 0.0226(3) Uani 1 1 d . . . C15 C 0.2934(3) 0.94260(10) 0.18765(9) 0.0247(3) Uani 1 1 d . . . H15 H 0.2575 0.9000 0.2167 0.030 Uiso 1 1 calc R . . C14 C 0.1495(3) 0.95126(10) 0.12499(9) 0.0245(3) Uani 1 1 d . . . H14 H 0.1901 0.9928 0.0954 0.029 Uiso 1 1 calc R . . N1 N -0.3823(3) 0.15793(8) 0.01262(7) 0.0237(3) Uani 1 1 d . . . N3 N 0.6501(3) 0.28154(9) 0.21772(8) 0.0261(3) Uani 1 1 d . . . N2 N 0.4385(3) 0.24364(9) 0.17506(8) 0.0238(3) Uani 1 1 d . . . C1 C 0.0276(3) 0.23528(9) 0.09495(8) 0.0206(3) Uani 1 1 d . . . C6 C 0.2327(3) 0.28246(10) 0.14047(8) 0.0219(3) Uani 1 1 d . . . O1 O 0.2079(3) 0.35307(7) 0.14519(7) 0.0317(3) Uani 1 1 d . . . C3 C -0.2251(3) 0.12086(10) 0.06374(9) 0.0238(3) Uani 1 1 d . . . H3 H -0.2561 0.0674 0.0713 0.029 Uiso 1 1 calc R . . C5 C -0.1328(4) 0.27331(10) 0.04075(9) 0.0253(3) Uani 1 1 d . . . H5 H -0.1029 0.3264 0.0310 0.030 Uiso 1 1 calc R . . C2 C -0.0186(3) 0.15739(9) 0.10617(9) 0.0230(3) Uani 1 1 d . . . H2 H 0.0887 0.1295 0.1422 0.028 Uiso 1 1 calc R . . C4 C -0.3359(4) 0.23289(10) 0.00124(9) 0.0265(4) Uani 1 1 d . . . H4 H -0.4462 0.2593 -0.0352 0.032 Uiso 1 1 calc R . . O2 O -0.3333(3) 0.59205(7) 0.02592(7) 0.0278(3) Uani 1 1 d . . . C7 C 0.0482(3) 0.58099(9) 0.11130(8) 0.0212(3) Uani 1 1 d . . . N4 N 0.4585(3) 0.56435(8) 0.18695(8) 0.0232(3) Uani 1 1 d . . . C11 C 0.0580(3) 0.66018(10) 0.12481(9) 0.0242(3) Uani 1 1 d . . . H11 H -0.0798 0.6933 0.1037 0.029 Uiso 1 1 calc R . . C9 C 0.4666(3) 0.64042(10) 0.20006(9) 0.0246(3) Uani 1 1 d . . . H9 H 0.6110 0.6608 0.2314 0.030 Uiso 1 1 calc R . . N5 N -0.2176(3) 0.47118(9) 0.06499(8) 0.0254(3) Uani 1 1 d . . . C8 C 0.2545(3) 0.53496(10) 0.14291(9) 0.0226(3) Uani 1 1 d . . . H8 H 0.2515 0.4809 0.1331 0.027 Uiso 1 1 calc R . . C12 C -0.1837(3) 0.54817(10) 0.06388(8) 0.0220(3) Uani 1 1 d . . . C10 C 0.2720(4) 0.69058(10) 0.16968(9) 0.0252(3) Uani 1 1 d . . . H10 H 0.2838 0.7446 0.1791 0.030 Uiso 1 1 calc R . . H1 H 0.457(5) 0.1925(14) 0.1693(13) 0.034(6) Uiso 1 1 d . . . H13 H -0.366(5) 0.4511(15) 0.0377(14) 0.038(6) Uiso 1 1 d . . . H12 H -0.110(5) 0.4413(15) 0.0925(14) 0.039(6) Uiso 1 1 d . . . H7 H 0.688(5) 0.3273(17) 0.1944(15) 0.045(7) Uiso 1 1 d . . . H16 H -0.361(5) 0.8912(15) 0.0277(15) 0.055(8) Uiso 1 1 d D . . H6 H 0.583(6) 0.2964(16) 0.2599(15) 0.048(7) Uiso 1 1 d . . . H17 H 0.811(5) 1.0065(15) 0.2768(16) 0.064(9) Uiso 1 1 d 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 O3 0.0301(7) 0.0235(6) 0.0312(7) 0.0020(5) -0.0054(5) -0.0021(5) O6 0.0233(6) 0.0244(6) 0.0295(6) -0.0007(5) -0.0059(5) -0.0009(5) O4 0.0267(6) 0.0264(6) 0.0287(6) 0.0038(5) -0.0086(5) -0.0056(5) O5 0.0283(6) 0.0254(6) 0.0310(6) 0.0041(5) -0.0040(5) -0.0037(5) C16 0.0198(7) 0.0242(8) 0.0226(7) -0.0019(6) 0.0009(6) -0.0011(6) C13 0.0220(7) 0.0214(7) 0.0234(7) -0.0020(6) -0.0012(6) 0.0012(6) C15 0.0214(8) 0.0255(8) 0.0263(8) -0.0010(6) -0.0005(6) -0.0030(6) C14 0.0224(8) 0.0233(7) 0.0267(8) -0.0020(6) -0.0005(6) -0.0009(6) N1 0.0220(7) 0.0250(7) 0.0230(7) 0.0000(5) -0.0019(5) -0.0014(5) N3 0.0234(7) 0.0262(7) 0.0270(7) -0.0037(6) -0.0037(6) -0.0026(6) N2 0.0220(7) 0.0215(7) 0.0261(7) -0.0024(5) -0.0035(5) 0.0003(5) C1 0.0198(7) 0.0218(7) 0.0200(7) -0.0009(5) 0.0018(6) 0.0004(6) C6 0.0233(8) 0.0205(7) 0.0218(7) 0.0003(6) 0.0022(6) -0.0012(6) O1 0.0338(7) 0.0193(6) 0.0392(7) -0.0030(5) -0.0068(6) -0.0001(5) C3 0.0256(8) 0.0208(7) 0.0240(8) 0.0003(6) -0.0007(6) -0.0007(6) C5 0.0280(8) 0.0197(7) 0.0269(8) 0.0033(6) -0.0016(6) -0.0019(6) C2 0.0248(8) 0.0208(7) 0.0219(7) 0.0005(6) -0.0025(6) 0.0012(6) C4 0.0280(8) 0.0253(8) 0.0245(8) 0.0030(6) -0.0030(6) 0.0003(7) O2 0.0238(6) 0.0248(6) 0.0318(6) 0.0027(5) -0.0078(5) -0.0001(5) C7 0.0183(7) 0.0231(7) 0.0215(7) 0.0002(6) 0.0003(6) -0.0011(6) N4 0.0190(6) 0.0239(7) 0.0256(7) 0.0019(5) -0.0011(5) -0.0001(5) C11 0.0214(7) 0.0231(8) 0.0275(8) 0.0002(6) 0.0005(6) 0.0015(6) C9 0.0230(8) 0.0259(8) 0.0243(8) -0.0027(6) 0.0005(6) -0.0043(6) N5 0.0245(7) 0.0220(7) 0.0276(7) 0.0004(5) -0.0047(6) -0.0003(5) C8 0.0196(7) 0.0217(8) 0.0258(8) -0.0002(6) -0.0001(6) -0.0016(6) C12 0.0199(7) 0.0244(8) 0.0211(7) -0.0004(6) 0.0001(6) 0.0007(6) C10 0.0256(8) 0.0213(8) 0.0282(8) -0.0015(6) 0.0014(6) -0.0014(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 O3 C13 1.224(2) . ? O6 C16 1.309(2) . ? O6 H17 0.941(18) . ? O4 C13 1.312(2) . ? O4 H16 0.935(17) . ? O5 C16 1.226(2) . ? C16 C15 1.490(2) . ? C13 C14 1.493(2) . ? C15 C14 1.326(2) . ? C15 H15 0.9500 . ? C14 H14 0.9500 . ? N1 C4 1.336(2) . ? N1 C3 1.340(2) . ? N3 N2 1.419(2) . ? N3 H7 0.94(3) . ? N3 H6 0.95(3) . ? N2 C6 1.339(2) . ? N2 H1 0.89(2) . ? C1 C2 1.385(2) . ? C1 C5 1.394(2) . ? C1 C6 1.505(2) . ? C6 O1 1.229(2) . ? C3 C2 1.389(2) . ? C3 H3 0.9500 . ? C5 C4 1.383(2) . ? C5 H5 0.9500 . ? C2 H2 0.9500 . ? C4 H4 0.9500 . ? O2 C12 1.237(2) . ? C7 C8 1.387(2) . ? C7 C11 1.390(2) . ? C7 C12 1.499(2) . ? N4 C9 1.335(2) . ? N4 C8 1.345(2) . ? C11 C10 1.395(2) . ? C11 H11 0.9500 . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? N5 C12 1.339(2) . ? N5 H13 0.92(3) . ? N5 H12 0.88(3) . ? C8 H8 0.9500 . ? C10 H10 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 O6 H17 107.1(19) . . ? C13 O4 H16 111.3(18) . . ? O5 C16 O6 124.42(15) . . ? O5 C16 C15 123.01(15) . . ? O6 C16 C15 112.57(15) . . ? O3 C13 O4 124.38(16) . . ? O3 C13 C14 123.76(15) . . ? O4 C13 C14 111.84(14) . . ? C14 C15 C16 121.64(16) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C14 C13 122.04(16) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C4 N1 C3 118.64(14) . . ? N2 N3 H7 107.5(17) . . ? N2 N3 H6 106.6(17) . . ? H7 N3 H6 107(2) . . ? C6 N2 N3 122.35(14) . . ? C6 N2 H1 121.3(16) . . ? N3 N2 H1 116.1(16) . . ? C2 C1 C5 118.49(15) . . ? C2 C1 C6 123.58(14) . . ? C5 C1 C6 117.86(15) . . ? O1 C6 N2 122.66(15) . . ? O1 C6 C1 120.58(15) . . ? N2 C6 C1 116.76(14) . . ? N1 C3 C2 122.74(15) . . ? N1 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C4 C5 C1 119.28(15) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? C1 C2 C3 118.65(15) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? N1 C4 C5 122.19(15) . . ? N1 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C8 C7 C11 118.36(15) . . ? C8 C7 C12 122.32(15) . . ? C11 C7 C12 119.32(14) . . ? C9 N4 C8 119.33(14) . . ? C7 C11 C10 119.32(15) . . ? C7 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? N4 C9 C10 122.25(15) . . ? N4 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C12 N5 H13 117.3(16) . . ? C12 N5 H12 121.5(17) . . ? H13 N5 H12 121(2) . . ? N4 C8 C7 122.12(15) . . ? N4 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? O2 C12 N5 123.04(15) . . ? O2 C12 C7 119.75(15) . . ? N5 C12 C7 117.21(14) . . ? C9 C10 C11 118.60(15) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.309 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 935251' ####################################################################### # # 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_publication_text #====END data_INHNASA #TrackingRef 'CIF-Srinivasulu INH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N5 O6' _chemical_formula_weight 377.36 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.1175(10) _cell_length_b 17.467(4) _cell_length_c 18.763(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.71(3) _cell_angle_gamma 90.00 _cell_volume 1665.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5612 _cell_measurement_theta_min 2.1858 _cell_measurement_theta_max 31.0512 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9502 _exptl_absorpt_correction_T_max 0.9656 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11614 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4027 _reflns_number_gt 3888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0683P)^2^+0.6278P] 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 4027 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 O3 O -0.09357(18) 0.16542(5) 0.12350(5) 0.0233(2) Uani 1 1 d . . . O6 O 0.71228(17) 0.03906(5) 0.25967(5) 0.0226(2) Uani 1 1 d . . . O4 O -0.25597(18) 0.07177(5) 0.04979(5) 0.0237(2) Uani 1 1 d . . . O5 O 0.50978(18) -0.05562(5) 0.19414(5) 0.0228(2) Uani 1 1 d . . . C13 C -0.0839(2) 0.10029(7) 0.10105(7) 0.0177(2) Uani 1 1 d . . . C16 C 0.5242(2) 0.01141(7) 0.21254(7) 0.0178(2) Uani 1 1 d . . . C15 C 0.3288(2) 0.07241(7) 0.18492(7) 0.0189(2) Uani 1 1 d . . . H15A H 0.2432 0.0931 0.2255 0.023 Uiso 1 1 calc R . . H15B H 0.4235 0.1149 0.1643 0.023 Uiso 1 1 calc R . . C14 C 0.1205(2) 0.04188(7) 0.12850(7) 0.0191(2) Uani 1 1 d . . . H4A H 0.2070 0.0225 0.0876 0.023 Uiso 1 1 calc R . . H4B H 0.0313 -0.0019 0.1489 0.023 Uiso 1 1 calc R . . N4 N 0.4488(2) 0.43830(6) 0.18776(6) 0.0191(2) Uani 1 1 d . . . C7 C 0.0418(2) 0.42030(7) 0.11259(6) 0.0170(2) Uani 1 1 d . . . O2 O -0.33274(18) 0.40878(5) 0.02597(5) 0.0238(2) Uani 1 1 d . . . C12 C -0.1863(2) 0.45231(7) 0.06419(7) 0.0176(2) Uani 1 1 d . . . N5 N -0.2215(2) 0.52823(6) 0.06536(6) 0.0210(2) Uani 1 1 d . . . C8 C 0.2465(2) 0.46616(7) 0.14354(7) 0.0185(2) Uani 1 1 d . . . H8 H 0.2427 0.5194 0.1329 0.022 Uiso 1 1 calc R . . C11 C 0.0531(2) 0.34211(7) 0.12696(7) 0.0192(2) Uani 1 1 d . . . H11 H -0.0824 0.3090 0.1062 0.023 Uiso 1 1 calc R . . C9 C 0.4572(2) 0.36309(7) 0.20180(7) 0.0201(2) Uani 1 1 d . . . H9 H 0.6002 0.3434 0.2333 0.024 Uiso 1 1 calc R . . C10 C 0.2646(2) 0.31304(7) 0.17198(7) 0.0207(3) Uani 1 1 d . . . H10 H 0.2770 0.2598 0.1821 0.025 Uiso 1 1 calc R . . N3 N 0.6485(2) 0.72057(6) 0.21739(6) 0.0221(2) Uani 1 1 d . . . N1 N -0.3736(2) 0.83817(6) 0.00940(6) 0.0201(2) Uani 1 1 d . . . N2 N 0.4414(2) 0.75674(6) 0.17290(6) 0.0202(2) Uani 1 1 d . . . O1 O 0.2147(2) 0.64788(5) 0.14502(5) 0.0264(2) Uani 1 1 d . . . C1 C 0.0354(2) 0.76305(7) 0.09221(7) 0.0178(2) Uani 1 1 d . . . C4 C -0.2100(2) 0.87612(7) 0.05800(7) 0.0215(3) Uani 1 1 d . . . H4 H -0.2362 0.9295 0.0636 0.026 Uiso 1 1 calc R . . C6 C 0.2386(2) 0.71753(7) 0.13872(7) 0.0184(2) Uani 1 1 d . . . C2 C -0.1309(2) 0.72383(7) 0.04057(7) 0.0210(3) Uani 1 1 d . . . H2 H -0.1061 0.6707 0.0327 0.025 Uiso 1 1 calc R . . C3 C -0.3328(2) 0.76324(7) 0.00078(7) 0.0219(3) Uani 1 1 d . . . H3 H -0.4467 0.7360 -0.0340 0.026 Uiso 1 1 calc R . . C5 C -0.0040(2) 0.84114(7) 0.10057(7) 0.0208(3) Uani 1 1 d . . . H5 H 0.1076 0.8699 0.1347 0.025 Uiso 1 1 calc R . . H7 H 0.691(4) 0.6743(12) 0.1952(11) 0.037(5) Uiso 1 1 d . . . H12 H -0.121(4) 0.5579(11) 0.0969(11) 0.034(5) Uiso 1 1 d . . . H6 H 0.581(3) 0.7048(10) 0.2597(10) 0.025(4) Uiso 1 1 d . . . H13 H -0.364(4) 0.5493(12) 0.0363(11) 0.042(5) Uiso 1 1 d . . . H1 H 0.461(4) 0.8070(11) 0.1680(11) 0.035(5) Uiso 1 1 d . . . H17 H 0.831(4) -0.0030(13) 0.2767(12) 0.053(6) Uiso 1 1 d . . . H16 H -0.383(5) 0.1124(15) 0.0307(13) 0.061(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 O3 0.0240(4) 0.0176(4) 0.0269(5) -0.0007(3) -0.0028(4) 0.0012(3) O6 0.0185(4) 0.0213(4) 0.0259(5) 0.0002(4) -0.0055(4) 0.0008(3) O4 0.0230(4) 0.0206(4) 0.0247(5) -0.0025(4) -0.0092(4) 0.0036(3) O5 0.0227(4) 0.0199(4) 0.0248(5) -0.0017(3) -0.0016(4) 0.0026(3) C13 0.0170(5) 0.0180(5) 0.0178(6) 0.0009(4) 0.0011(4) -0.0007(4) C16 0.0156(5) 0.0205(6) 0.0172(6) 0.0018(4) 0.0014(4) 0.0002(4) C15 0.0166(5) 0.0173(5) 0.0218(6) -0.0002(4) -0.0020(4) 0.0013(4) C14 0.0178(5) 0.0186(5) 0.0200(6) -0.0001(4) -0.0018(4) 0.0023(4) N4 0.0161(5) 0.0198(5) 0.0207(5) -0.0012(4) -0.0001(4) -0.0003(4) C7 0.0154(5) 0.0187(5) 0.0170(6) -0.0005(4) 0.0021(4) 0.0009(4) O2 0.0208(4) 0.0208(5) 0.0277(5) -0.0018(4) -0.0055(4) -0.0007(3) C12 0.0151(5) 0.0196(5) 0.0179(6) 0.0008(4) 0.0010(4) -0.0006(4) N5 0.0202(5) 0.0179(5) 0.0235(6) 0.0003(4) -0.0035(4) 0.0008(4) C8 0.0172(5) 0.0181(5) 0.0199(6) 0.0007(4) 0.0013(4) 0.0009(4) C11 0.0187(5) 0.0175(6) 0.0211(6) -0.0012(4) 0.0012(4) -0.0016(4) C9 0.0183(5) 0.0223(6) 0.0194(6) 0.0017(5) 0.0012(4) 0.0035(4) C10 0.0222(6) 0.0165(5) 0.0233(6) 0.0019(4) 0.0027(5) 0.0011(4) N3 0.0201(5) 0.0224(5) 0.0228(6) 0.0033(4) -0.0022(4) 0.0043(4) N1 0.0190(5) 0.0215(5) 0.0190(5) 0.0002(4) -0.0009(4) 0.0012(4) N2 0.0195(5) 0.0180(5) 0.0223(5) 0.0031(4) -0.0016(4) 0.0005(4) O1 0.0312(5) 0.0169(4) 0.0290(5) 0.0021(4) -0.0056(4) 0.0008(4) C1 0.0187(5) 0.0179(6) 0.0168(6) 0.0011(4) 0.0021(4) -0.0002(4) C4 0.0239(6) 0.0166(6) 0.0228(6) -0.0010(4) -0.0018(5) 0.0012(4) C6 0.0202(5) 0.0179(5) 0.0173(6) -0.0003(4) 0.0027(4) 0.0015(4) C2 0.0251(6) 0.0165(5) 0.0207(6) -0.0013(4) 0.0002(5) 0.0005(4) C3 0.0235(6) 0.0213(6) 0.0200(6) -0.0018(5) -0.0009(5) -0.0008(4) C5 0.0215(6) 0.0182(6) 0.0214(6) -0.0005(4) -0.0028(5) -0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C13 1.2161(15) . ? O6 C16 1.3201(15) . ? O6 H17 0.98(2) . ? O4 C13 1.3231(16) . ? O4 H16 1.00(3) . ? O5 C16 1.2205(16) . ? C13 C14 1.5081(16) . ? C16 C15 1.5110(16) . ? C15 C14 1.5093(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C14 H4A 0.9900 . ? C14 H4B 0.9900 . ? N4 C9 1.3397(16) . ? N4 C8 1.3403(16) . ? C7 C8 1.3905(17) . ? C7 C11 1.3920(17) . ? C7 C12 1.5010(17) . ? O2 C12 1.2362(15) . ? C12 N5 1.3389(16) . ? N5 H12 0.90(2) . ? N5 H13 0.93(2) . ? C8 H8 0.9500 . ? C11 C10 1.3892(18) . ? C11 H11 0.9500 . ? C9 C10 1.3856(18) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N3 N2 1.4184(15) . ? N3 H7 0.95(2) . ? N3 H6 0.943(18) . ? N1 C3 1.3382(17) . ? N1 C4 1.3393(17) . ? N2 C6 1.3426(16) . ? N2 H1 0.89(2) . ? O1 C6 1.2298(16) . ? C1 C5 1.3904(17) . ? C1 C2 1.3928(17) . ? C1 C6 1.5042(17) . ? C4 C5 1.3877(18) . ? C4 H4 0.9500 . ? C2 C3 1.3850(18) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C5 H5 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 O6 H17 108.6(13) . . ? C13 O4 H16 110.1(14) . . ? O3 C13 O4 123.61(11) . . ? O3 C13 C14 124.69(11) . . ? O4 C13 C14 111.69(10) . . ? O5 C16 O6 123.77(11) . . ? O5 C16 C15 124.31(11) . . ? O6 C16 C15 111.91(10) . . ? C14 C15 C16 112.11(10) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C13 C14 C15 113.92(10) . . ? C13 C14 H4A 108.8 . . ? C15 C14 H4A 108.8 . . ? C13 C14 H4B 108.8 . . ? C15 C14 H4B 108.8 . . ? H4A C14 H4B 107.7 . . ? C9 N4 C8 118.85(11) . . ? C8 C7 C11 118.18(11) . . ? C8 C7 C12 122.20(11) . . ? C11 C7 C12 119.62(11) . . ? O2 C12 N5 123.04(11) . . ? O2 C12 C7 119.86(11) . . ? N5 C12 C7 117.09(11) . . ? C12 N5 H12 120.8(12) . . ? C12 N5 H13 118.5(13) . . ? H12 N5 H13 120.3(18) . . ? N4 C8 C7 122.63(11) . . ? N4 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? C10 C11 C7 119.21(11) . . ? C10 C11 H11 120.4 . . ? C7 C11 H11 120.4 . . ? N4 C9 C10 122.29(11) . . ? N4 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C9 C10 C11 118.82(11) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N2 N3 H7 108.4(12) . . ? N2 N3 H6 107.8(11) . . ? H7 N3 H6 104.3(16) . . ? C3 N1 C4 118.18(11) . . ? C6 N2 N3 122.45(11) . . ? C6 N2 H1 122.9(13) . . ? N3 N2 H1 114.6(13) . . ? C5 C1 C2 118.44(11) . . ? C5 C1 C6 123.55(11) . . ? C2 C1 C6 117.92(11) . . ? N1 C4 C5 123.12(11) . . ? N1 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? O1 C6 N2 122.58(11) . . ? O1 C6 C1 120.61(11) . . ? N2 C6 C1 116.80(11) . . ? C3 C2 C1 119.15(11) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? N1 C3 C2 122.57(11) . . ? N1 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C4 C5 C1 118.52(11) . . ? C4 C5 H5 120.7 . . ? C1 C5 H5 120.7 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.352 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.054 #====END _database_code_depnum_ccdc_archive 'CCDC 935252'