data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year 2012 _journal_volume 14 _journal_page_first ? _publ_contact_author_address ; Department of Chemistry University of Calcutta 92 Acharya Prafulla Chandra Road Kolkata 700 009 India ; _publ_contact_author_email nguchhait@yahoo.com loop_ _publ_author_name _publ_author_address 'Sasanka Dalapati' ; Department of Chemistry University of Calcutta 92, Acharya Prafulla Chandra Road Kolkata 700 009 India ; Md.A.Alam ; Department of Chemistry University of Calcutta 92, Acharya Prafulla Chandra Road Kolkata 700 009 India ; 'Sankar Jana' ; Department of Chemistry University of Calcutta 92, Acharya Prafulla Chandra Road Kolkata 700 009 India ; 'Nikhil Guchhait' '' data_2.H2PO4- _database_code_depnum_ccdc_archive 'CCDC 867101' #TrackingRef '2.H2PO4-.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N3 O2, C16 H36 N, H2 O4 P, H2 O' _chemical_formula_sum 'C29 H53 N4 O7 P' _chemical_formula_weight 600.72 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.7398(15) _cell_length_b 14.884(2) _cell_length_c 23.545(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.880(2) _cell_angle_gamma 90.00 _cell_volume 3372.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 26.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 23482 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.48 _reflns_number_total 6400 _reflns_number_gt 3731 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0896P)^2^+2.2371P] 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 6400 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.2101 _refine_ls_wR_factor_gt 0.1780 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 P1 P -0.21625(11) 0.98233(6) 0.98196(5) 0.0782(3) Uani 1 1 d . . . N4 N 0.0604(2) 0.70876(14) 0.99920(10) 0.0493(6) Uani 1 1 d . . . O7 O -0.3279(3) 1.04766(15) 0.96000(11) 0.0852(8) Uani 1 1 d . . . H7 H -0.3822 1.0522 0.9832 0.128 Uiso 1 1 calc R . . O5 O -0.1472(3) 1.00516(18) 1.04278(11) 0.0831(8) Uani 1 1 d . . . O2 O -0.0245(4) 0.50165(18) 1.12297(12) 0.0938(9) Uani 1 1 d . . . O1W O -0.5478(3) 0.86839(17) 0.96361(12) 0.0893(8) Uani 1 1 d . . . H1W1 H -0.4645 0.8549 0.9774 0.107 Uiso 1 1 d R . . H2W1 H -0.5455 0.9022 0.9347 0.107 Uiso 1 1 d R . . N2 N 0.1368(4) 0.4744(3) 1.33202(18) 0.0806(10) Uani 1 1 d . . . O6 O -0.1088(3) 0.9680(3) 0.94295(13) 0.1258(13) Uani 1 1 d . . . N3 N -0.1346(5) 0.49900(18) 1.14289(15) 0.0805(9) Uani 1 1 d . . . O1 O -0.2478(4) 0.5015(2) 1.11184(14) 0.1135(11) Uani 1 1 d . . . N1 N -0.1073(5) 0.4727(3) 1.38017(16) 0.0836(10) Uani 1 1 d . . . C21 C 0.0192(3) 0.77003(19) 1.04542(13) 0.0551(7) Uani 1 1 d . . . H21A H 0.0933 0.8133 1.0559 0.066 Uiso 1 1 calc R . . H21B H -0.0630 0.8033 1.0290 0.066 Uiso 1 1 calc R . . C17 C -0.0530(3) 0.64117(18) 0.97893(14) 0.0546(8) Uani 1 1 d . . . H17A H -0.0190 0.6006 0.9520 0.066 Uiso 1 1 calc R . . H17B H -0.0695 0.6057 1.0118 0.066 Uiso 1 1 calc R . . C5 C -0.0002(4) 0.4863(2) 1.23822(15) 0.0644(9) Uani 1 1 d . . . H5 H 0.0800 0.4875 1.2213 0.077 Uiso 1 1 calc R . . C29 C 0.0873(3) 0.77112(18) 0.95081(12) 0.0528(7) Uani 1 1 d . . . H29A H 0.0021 0.8035 0.9374 0.063 Uiso 1 1 calc R . . H29B H 0.1562 0.8150 0.9667 0.063 Uiso 1 1 calc R . . C20 C -0.0103(3) 0.7247(2) 1.09971(13) 0.0611(8) Uani 1 1 d . . . H20A H -0.0856 0.6820 1.0903 0.073 Uiso 1 1 calc R . . H20B H 0.0714 0.6919 1.1173 0.073 Uiso 1 1 calc R . . C28 C 0.1360(4) 0.7283(2) 0.89971(14) 0.0636(8) Uani 1 1 d . . . H28A H 0.0671 0.6856 0.8821 0.076 Uiso 1 1 calc R . . H28B H 0.2221 0.6961 0.9119 0.076 Uiso 1 1 calc R . . C25 C 0.1891(3) 0.65417(19) 1.02187(14) 0.0561(8) Uani 1 1 d . . . H25A H 0.1672 0.6153 1.0523 0.067 Uiso 1 1 calc R . . H25B H 0.2108 0.6159 0.9911 0.067 Uiso 1 1 calc R . . O4 O -0.2822(4) 0.88891(18) 0.9900(2) 0.1594(18) Uani 1 1 d . . . C6 C 0.0102(4) 0.4792(2) 1.29733(15) 0.0636(9) Uani 1 1 d . . . C1 C -0.1147(4) 0.4767(2) 1.32150(16) 0.0660(9) Uani 1 1 d . . . C4 C -0.1285(4) 0.4917(2) 1.20412(15) 0.0667(9) Uani 1 1 d . . . C24 C 0.3168(3) 0.7078(2) 1.04480(16) 0.0707(9) Uani 1 1 d . . . H24A H 0.3006 0.7405 1.0788 0.085 Uiso 1 1 calc R . . H24B H 0.3348 0.7512 1.0161 0.085 Uiso 1 1 calc R . . C27 C 0.1589(4) 0.7999(2) 0.85653(14) 0.0703(9) Uani 1 1 d . . . H27A H 0.0700 0.8261 0.8408 0.084 Uiso 1 1 calc R . . H27B H 0.2162 0.8472 0.8762 0.084 Uiso 1 1 calc R . . C16 C -0.1896(3) 0.6791(2) 0.95069(16) 0.0680(9) Uani 1 1 d . . . H16A H -0.1760 0.7123 0.9165 0.082 Uiso 1 1 calc R . . H16B H -0.2248 0.7205 0.9768 0.082 Uiso 1 1 calc R . . C23 C 0.4422(4) 0.6475(3) 1.05989(19) 0.0824(11) Uani 1 1 d . . . H23A H 0.4563 0.6135 1.0261 0.099 Uiso 1 1 calc R . . H23B H 0.4247 0.6051 1.0892 0.099 Uiso 1 1 calc R . . C8 C 0.2943(4) 0.5719(3) 1.28446(15) 0.0698(9) Uani 1 1 d . . . C3 C -0.2498(4) 0.4902(2) 1.22718(18) 0.0780(11) Uani 1 1 d . . . H3 H -0.3357 0.4941 1.2037 0.094 Uiso 1 1 calc R . . C19 C -0.0492(5) 0.7928(3) 1.14121(16) 0.0858(11) Uani 1 1 d . . . H19A H 0.0270 0.8349 1.1503 0.103 Uiso 1 1 calc R . . H19B H -0.1293 0.8262 1.1227 0.103 Uiso 1 1 calc R . . C7 C 0.2671(4) 0.4824(3) 1.31087(17) 0.0783(10) Uani 1 1 d . . . H7A H 0.2712 0.4359 1.2823 0.094 Uiso 1 1 calc R . . H7B H 0.3415 0.4709 1.3425 0.094 Uiso 1 1 calc R . . C2 C -0.2410(4) 0.4830(2) 1.28580(18) 0.0779(10) Uani 1 1 d . . . H2 H -0.3223 0.4823 1.3019 0.094 Uiso 1 1 calc R . . C13 C 0.2530(4) 0.6520(3) 1.30593(18) 0.0850(11) Uani 1 1 d . . . H13 H 0.2039 0.6515 1.3368 0.102 Uiso 1 1 calc R . . C9 C 0.3675(5) 0.5758(4) 1.2389(2) 0.0982(13) Uani 1 1 d . . . H9 H 0.3960 0.5229 1.2233 0.118 Uiso 1 1 calc R . . C15 C -0.2950(4) 0.6047(3) 0.9342(2) 0.0900(12) Uani 1 1 d . . . H15A H -0.2564 0.5613 0.9103 0.108 Uiso 1 1 calc R . . H15B H -0.3120 0.5739 0.9688 0.108 Uiso 1 1 calc R . . C18 C -0.0822(5) 0.7540(3) 1.19569(17) 0.1048(15) Uani 1 1 d . . . H18A H -0.1070 0.8015 1.2198 0.157 Uiso 1 1 calc R . . H18B H -0.0024 0.7228 1.2152 0.157 Uiso 1 1 calc R . . H18C H -0.1585 0.7129 1.1873 0.157 Uiso 1 1 calc R . . C26 C 0.2272(5) 0.7648(3) 0.80814(18) 0.1022(14) Uani 1 1 d . . . H26A H 0.2389 0.8130 0.7822 0.153 Uiso 1 1 calc R . . H26B H 0.1701 0.7188 0.7880 0.153 Uiso 1 1 calc R . . H26C H 0.3165 0.7401 0.8233 0.153 Uiso 1 1 calc R . . C22 C 0.5737(4) 0.7006(3) 1.0817(2) 0.1088(16) Uani 1 1 d . . . H22A H 0.6506 0.6600 1.0905 0.163 Uiso 1 1 calc R . . H22B H 0.5611 0.7331 1.1157 0.163 Uiso 1 1 calc R . . H22C H 0.5922 0.7421 1.0526 0.163 Uiso 1 1 calc R . . C12 C 0.2836(5) 0.7325(3) 1.2823(2) 0.1049(14) Uani 1 1 d . . . H12 H 0.2545 0.7860 1.2970 0.126 Uiso 1 1 calc R . . C14 C -0.4307(4) 0.6391(3) 0.9025(2) 0.1122(16) Uani 1 1 d . . . H14A H -0.4934 0.5896 0.8929 0.168 Uiso 1 1 calc R . . H14B H -0.4148 0.6686 0.8678 0.168 Uiso 1 1 calc R . . H14C H -0.4707 0.6809 0.9264 0.168 Uiso 1 1 calc R . . C11 C 0.3567(6) 0.7344(4) 1.2371(2) 0.1135(16) Uani 1 1 d . . . H11 H 0.3770 0.7890 1.2210 0.136 Uiso 1 1 calc R . . C10 C 0.3988(6) 0.6573(5) 1.2161(2) 0.1220(18) Uani 1 1 d . . . H10 H 0.4499 0.6586 1.1858 0.146 Uiso 1 1 calc R . . H1B H -0.022(4) 0.455(2) 1.3990(14) 0.057(10) Uiso 1 1 d . . . H1A H -0.179(4) 0.464(2) 1.3891(16) 0.066(13) Uiso 1 1 d . . . H5A H -0.052(3) 1.0160(16) 1.0488(10) 0.030(7) Uiso 1 1 d . . . H2A H 0.136(4) 0.469(3) 1.3627(17) 0.076(14) 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 P1 0.0844(7) 0.0564(5) 0.0910(8) -0.0132(5) 0.0045(6) 0.0045(5) N4 0.0548(14) 0.0382(11) 0.0562(14) 0.0024(10) 0.0128(11) 0.0014(10) O7 0.0977(19) 0.0609(14) 0.0954(19) 0.0016(13) 0.0104(15) 0.0102(13) O5 0.088(2) 0.0889(18) 0.0724(17) -0.0075(13) 0.0122(15) 0.0075(15) O2 0.137(3) 0.0720(17) 0.0750(18) -0.0097(13) 0.0251(19) -0.0014(17) O1W 0.0774(17) 0.0778(17) 0.111(2) 0.0117(15) 0.0107(15) -0.0028(13) N2 0.081(3) 0.096(2) 0.066(2) 0.0069(19) 0.016(2) 0.0029(18) O6 0.097(2) 0.199(4) 0.0787(19) -0.054(2) 0.0039(17) 0.025(2) N3 0.119(3) 0.0478(16) 0.071(2) -0.0094(14) 0.001(2) 0.0049(17) O1 0.138(3) 0.105(2) 0.086(2) -0.0045(16) -0.020(2) 0.014(2) N1 0.077(3) 0.096(3) 0.081(3) -0.0040(19) 0.024(2) -0.016(2) C21 0.0631(19) 0.0437(15) 0.0597(18) -0.0052(13) 0.0133(15) 0.0003(14) C17 0.0603(19) 0.0399(14) 0.0648(19) -0.0028(13) 0.0130(15) -0.0046(13) C5 0.074(2) 0.0522(17) 0.069(2) -0.0052(15) 0.0172(18) 0.0032(16) C29 0.0613(19) 0.0414(14) 0.0562(18) 0.0072(13) 0.0110(14) 0.0010(13) C20 0.064(2) 0.0574(18) 0.063(2) 0.0019(15) 0.0132(16) 0.0010(15) C28 0.077(2) 0.0543(17) 0.062(2) 0.0067(15) 0.0199(17) 0.0057(16) C25 0.062(2) 0.0433(15) 0.0640(19) 0.0074(14) 0.0134(16) 0.0081(14) O4 0.108(2) 0.0476(15) 0.304(5) 0.009(2) -0.026(3) 0.0017(16) C6 0.073(2) 0.0488(17) 0.067(2) -0.0020(15) 0.0078(19) 0.0027(16) C1 0.082(3) 0.0499(18) 0.070(2) -0.0052(15) 0.024(2) -0.0093(16) C4 0.086(3) 0.0429(16) 0.069(2) -0.0091(15) 0.006(2) 0.0022(16) C24 0.064(2) 0.0589(19) 0.088(2) 0.0142(17) 0.0102(18) 0.0030(16) C27 0.086(2) 0.064(2) 0.064(2) 0.0060(16) 0.0179(18) 0.0007(18) C16 0.064(2) 0.0550(18) 0.083(2) 0.0001(16) 0.0062(18) -0.0030(16) C23 0.065(2) 0.084(3) 0.097(3) 0.017(2) 0.009(2) 0.0083(19) C8 0.062(2) 0.083(2) 0.063(2) -0.0020(18) 0.0062(17) 0.0062(18) C3 0.077(3) 0.068(2) 0.085(3) -0.0160(19) -0.003(2) 0.0009(19) C19 0.120(3) 0.071(2) 0.073(2) -0.0085(19) 0.035(2) -0.005(2) C7 0.075(3) 0.080(2) 0.079(2) -0.0018(19) 0.009(2) 0.019(2) C2 0.066(2) 0.077(2) 0.092(3) -0.018(2) 0.018(2) -0.0109(19) C13 0.084(3) 0.085(3) 0.088(3) -0.003(2) 0.020(2) 0.011(2) C9 0.098(3) 0.114(4) 0.087(3) -0.014(3) 0.030(3) -0.004(3) C15 0.073(3) 0.075(2) 0.119(3) -0.012(2) 0.004(2) -0.015(2) C18 0.139(4) 0.113(3) 0.071(3) 0.000(2) 0.043(3) 0.006(3) C26 0.135(4) 0.099(3) 0.085(3) 0.019(2) 0.055(3) 0.027(3) C22 0.062(3) 0.116(3) 0.145(4) 0.038(3) 0.004(3) 0.000(2) C12 0.112(4) 0.081(3) 0.118(4) 0.006(3) 0.006(3) 0.006(3) C14 0.067(3) 0.121(4) 0.140(4) -0.007(3) -0.010(3) -0.010(3) C11 0.119(4) 0.118(4) 0.099(4) 0.031(3) 0.004(3) -0.019(3) C10 0.144(5) 0.149(5) 0.081(3) 0.003(3) 0.039(3) -0.026(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 P1 O7 1.490(3) . ? P1 O6 1.510(3) . ? P1 O5 1.524(3) . ? P1 O4 1.555(3) . ? N4 C17 1.516(4) . ? N4 C25 1.519(4) . ? N4 C21 1.520(4) . ? N4 C29 1.523(3) . ? O7 H7 0.8200 . ? O5 H5A 0.93(3) . ? O2 N3 1.235(4) . ? O1W H1W1 0.8500 . ? O1W H2W1 0.8499 . ? N2 C6 1.372(5) . ? N2 C7 1.438(5) . ? N2 H2A 0.73(4) . ? N3 O1 1.226(4) . ? N3 C4 1.438(5) . ? N1 C1 1.373(5) . ? N1 H1B 0.92(3) . ? N1 H1A 0.77(4) . ? C21 C20 1.512(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C17 C16 1.503(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C5 C4 1.379(5) . ? C5 C6 1.384(5) . ? C5 H5 0.9300 . ? C29 C28 1.502(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C20 C19 1.497(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C28 C27 1.512(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C25 C24 1.506(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C6 C1 1.421(5) . ? C1 C2 1.382(5) . ? C4 C3 1.375(5) . ? C24 C23 1.514(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C27 C26 1.499(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C16 C15 1.519(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C23 C22 1.525(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C8 C13 1.379(5) . ? C8 C9 1.378(6) . ? C8 C7 1.510(5) . ? C3 C2 1.374(5) . ? C3 H3 0.9300 . ? C19 C18 1.486(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C2 H2 0.9300 . ? C13 C12 1.374(6) . ? C13 H13 0.9300 . ? C9 C10 1.379(7) . ? C9 H9 0.9300 . ? C15 C14 1.505(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C12 C11 1.369(7) . ? C12 H12 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C11 C10 1.339(7) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? 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 O7 P1 O6 114.72(19) . . ? O7 P1 O5 111.91(15) . . ? O6 P1 O5 110.87(17) . . ? O7 P1 O4 109.42(17) . . ? O6 P1 O4 106.6(2) . . ? O5 P1 O4 102.5(2) . . ? C17 N4 C25 106.1(2) . . ? C17 N4 C21 111.3(2) . . ? C25 N4 C21 111.3(2) . . ? C17 N4 C29 111.7(2) . . ? C25 N4 C29 111.2(2) . . ? C21 N4 C29 105.3(2) . . ? P1 O7 H7 109.5 . . ? P1 O5 H5A 117.8(16) . . ? H1W1 O1W H2W1 107.7 . . ? C6 N2 C7 123.3(4) . . ? C6 N2 H2A 117(3) . . ? C7 N2 H2A 120(3) . . ? O1 N3 O2 121.7(4) . . ? O1 N3 C4 119.6(4) . . ? O2 N3 C4 118.6(4) . . ? C1 N1 H1B 114(2) . . ? C1 N1 H1A 112(3) . . ? H1B N1 H1A 128(4) . . ? C20 C21 N4 116.3(2) . . ? C20 C21 H21A 108.2 . . ? N4 C21 H21A 108.2 . . ? C20 C21 H21B 108.2 . . ? N4 C21 H21B 108.2 . . ? H21A C21 H21B 107.4 . . ? C16 C17 N4 116.3(2) . . ? C16 C17 H17A 108.2 . . ? N4 C17 H17A 108.2 . . ? C16 C17 H17B 108.2 . . ? N4 C17 H17B 108.2 . . ? H17A C17 H17B 107.4 . . ? C4 C5 C6 120.6(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C28 C29 N4 116.9(2) . . ? C28 C29 H29A 108.1 . . ? N4 C29 H29A 108.1 . . ? C28 C29 H29B 108.1 . . ? N4 C29 H29B 108.1 . . ? H29A C29 H29B 107.3 . . ? C19 C20 C21 110.5(3) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C29 C28 C27 109.7(3) . . ? C29 C28 H28A 109.7 . . ? C27 C28 H28A 109.7 . . ? C29 C28 H28B 109.7 . . ? C27 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? C24 C25 N4 115.7(2) . . ? C24 C25 H25A 108.4 . . ? N4 C25 H25A 108.4 . . ? C24 C25 H25B 108.4 . . ? N4 C25 H25B 108.4 . . ? H25A C25 H25B 107.4 . . ? N2 C6 C5 121.5(4) . . ? N2 C6 C1 120.4(3) . . ? C5 C6 C1 118.1(3) . . ? N1 C1 C2 121.2(4) . . ? N1 C1 C6 119.2(4) . . ? C2 C1 C6 119.4(3) . . ? C3 C4 C5 121.7(4) . . ? C3 C4 N3 119.5(4) . . ? C5 C4 N3 118.8(4) . . ? C25 C24 C23 111.2(3) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C26 C27 C28 113.2(3) . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27B 108.9 . . ? C28 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C17 C16 C15 110.8(3) . . ? C17 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C24 C23 C22 112.2(3) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C13 C8 C9 117.6(4) . . ? C13 C8 C7 122.1(3) . . ? C9 C8 C7 120.2(4) . . ? C4 C3 C2 118.3(4) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C18 C19 C20 114.3(3) . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? N2 C7 C8 115.9(3) . . ? N2 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? N2 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C3 C2 C1 121.9(4) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C8 C13 C12 120.8(4) . . ? C8 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C10 C9 C8 120.9(5) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C14 C15 C16 112.7(3) . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C27 C26 H26A 109.5 . . ? C27 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C27 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C11 C12 C13 120.3(5) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C11 C12 119.6(5) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C10 C9 120.8(5) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.613 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.040 data_2 _database_code_depnum_ccdc_archive 'CCDC 867102' #TrackingRef '2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N3 O2' _chemical_formula_sum 'C13 H13 N3 O2' _chemical_formula_weight 243.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.1110(4) _cell_length_b 5.9151(2) _cell_length_c 16.3090(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.0120(10) _cell_angle_gamma 90.00 _cell_volume 1188.44(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 26.40 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.995 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 12238 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2431 _reflns_number_gt 1958 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0574P)^2^+0.2633P] 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 2431 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O1 O 0.62374(11) 0.0333(3) 0.52329(7) 0.0762(4) Uani 1 1 d . . . O2 O 0.69691(11) 0.3460(2) 0.58249(7) 0.0742(4) Uani 1 1 d . . . N3 N 0.65660(10) 0.1598(3) 0.58675(7) 0.0521(3) Uani 1 1 d . . . N2 N 0.74755(11) 0.2723(2) 0.89901(8) 0.0485(3) Uani 1 1 d . . . N1 N 0.62797(13) -0.1089(3) 0.90554(10) 0.0580(4) Uani 1 1 d . . . C1 C 0.64962(10) 0.0864(2) 0.66912(8) 0.0402(3) Uani 1 1 d . . . C2 C 0.69957(10) 0.2185(2) 0.74272(8) 0.0384(3) Uani 1 1 d . . . H2 H 0.7359 0.3501 0.7379 0.046 Uiso 1 1 calc R . . C3 C 0.69502(10) 0.1539(2) 0.82289(8) 0.0364(3) Uani 1 1 d . . . C4 C 0.81704(12) 0.4631(2) 0.90018(9) 0.0471(3) Uani 1 1 d . . . H4A H 0.8352 0.5386 0.9562 0.057 Uiso 1 1 calc R . . H4B H 0.7772 0.5696 0.8555 0.057 Uiso 1 1 calc R . . C5 C 0.92106(11) 0.4000(2) 0.88516(8) 0.0391(3) Uani 1 1 d . . . C6 C 0.97069(13) 0.5553(3) 0.84790(10) 0.0519(4) Uani 1 1 d . . . H6 H 0.9383 0.6954 0.8304 0.062 Uiso 1 1 calc R . . C7 C 1.06806(14) 0.5053(3) 0.83623(11) 0.0610(4) Uani 1 1 d . . . H7 H 1.1004 0.6113 0.8108 0.073 Uiso 1 1 calc R . . C8 C 1.11681(13) 0.2994(3) 0.86216(10) 0.0580(4) Uani 1 1 d . . . H8 H 1.1826 0.2661 0.8550 0.070 Uiso 1 1 calc R . . C9 C 0.59595(11) -0.1109(3) 0.67304(9) 0.0469(3) Uani 1 1 d . . . H9 H 0.5645 -0.1987 0.6235 0.056 Uiso 1 1 calc R . . C10 C 0.59011(11) -0.1747(2) 0.75271(10) 0.0460(3) Uani 1 1 d . . . H10 H 0.5536 -0.3071 0.7564 0.055 Uiso 1 1 calc R . . C11 C 0.63742(10) -0.0460(2) 0.82776(9) 0.0402(3) Uani 1 1 d . . . C12 C 1.06797(13) 0.1433(3) 0.89869(11) 0.0549(4) Uani 1 1 d . . . H12 H 1.1008 0.0037 0.9163 0.066 Uiso 1 1 calc R . . C13 C 0.97022(12) 0.1921(2) 0.90952(9) 0.0470(3) Uani 1 1 d . . . H13 H 0.9372 0.0839 0.9335 0.056 Uiso 1 1 calc R . . H2A H 0.7186(16) 0.273(3) 0.9338(13) 0.069(6) Uiso 1 1 d . . . H1A H 0.5962(17) -0.244(4) 0.9052(13) 0.076(6) Uiso 1 1 d . . . H1B H 0.6638(19) -0.040(4) 0.9532(17) 0.091(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 O1 0.0767(8) 0.1156(11) 0.0366(6) -0.0197(6) 0.0196(5) -0.0116(8) O2 0.0909(9) 0.0893(9) 0.0461(6) 0.0101(6) 0.0283(6) -0.0193(8) N3 0.0434(7) 0.0801(9) 0.0329(6) -0.0013(6) 0.0133(5) 0.0024(6) N2 0.0474(7) 0.0680(8) 0.0355(6) -0.0107(5) 0.0211(5) -0.0088(6) N1 0.0668(9) 0.0644(9) 0.0492(8) 0.0090(7) 0.0282(7) -0.0071(7) C1 0.0347(7) 0.0547(8) 0.0314(6) -0.0003(5) 0.0117(5) 0.0040(6) C2 0.0356(7) 0.0451(7) 0.0359(7) 0.0001(5) 0.0140(5) -0.0004(5) C3 0.0309(6) 0.0467(7) 0.0329(6) -0.0006(5) 0.0125(5) 0.0035(5) C4 0.0492(8) 0.0502(8) 0.0411(7) -0.0118(6) 0.0145(6) -0.0006(6) C5 0.0425(7) 0.0415(7) 0.0298(6) -0.0052(5) 0.0080(5) -0.0043(5) C6 0.0581(9) 0.0451(8) 0.0502(8) 0.0041(6) 0.0156(7) -0.0053(7) C7 0.0590(10) 0.0710(10) 0.0580(9) 0.0017(8) 0.0264(8) -0.0182(8) C8 0.0454(9) 0.0742(11) 0.0565(9) -0.0154(8) 0.0204(7) -0.0085(8) C9 0.0405(7) 0.0549(8) 0.0422(7) -0.0109(6) 0.0103(6) -0.0013(6) C10 0.0391(7) 0.0437(7) 0.0544(8) 0.0008(6) 0.0151(6) -0.0028(6) C11 0.0333(7) 0.0476(7) 0.0415(7) 0.0065(6) 0.0154(5) 0.0063(5) C12 0.0466(9) 0.0519(8) 0.0631(9) -0.0048(7) 0.0148(7) 0.0043(7) C13 0.0475(8) 0.0453(8) 0.0475(8) 0.0039(6) 0.0155(6) -0.0028(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 O1 N3 1.2296(17) . ? O2 N3 1.2338(18) . ? N3 C1 1.4442(17) . ? N2 C3 1.3859(17) . ? N2 C4 1.447(2) . ? N2 H2A 0.78(2) . ? N1 C11 1.3675(18) . ? N1 H1A 0.90(2) . ? N1 H1B 0.86(3) . ? C1 C9 1.376(2) . ? C1 C2 1.3936(19) . ? C2 C3 1.3829(17) . ? C2 H2 0.9300 . ? C3 C11 1.4201(19) . ? C4 C5 1.513(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.381(2) . ? C5 C13 1.3821(19) . ? C6 C7 1.386(2) . ? C6 H6 0.9300 . ? C7 C8 1.373(3) . ? C7 H7 0.9300 . ? C8 C12 1.370(2) . ? C8 H8 0.9300 . ? C9 C10 1.380(2) . ? C9 H9 0.9300 . ? C10 C11 1.394(2) . ? C10 H10 0.9300 . ? C12 C13 1.383(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 O1 N3 O2 121.98(13) . . ? O1 N3 C1 118.97(14) . . ? O2 N3 C1 119.04(12) . . ? C3 N2 C4 121.58(12) . . ? C3 N2 H2A 115.8(15) . . ? C4 N2 H2A 116.5(15) . . ? C11 N1 H1A 115.1(13) . . ? C11 N1 H1B 120.8(16) . . ? H1A N1 H1B 122(2) . . ? C9 C1 C2 122.19(12) . . ? C9 C1 N3 119.64(12) . . ? C2 C1 N3 118.16(13) . . ? C3 C2 C1 119.98(12) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 N2 122.56(12) . . ? C2 C3 C11 118.62(12) . . ? N2 C3 C11 118.78(11) . . ? N2 C4 C5 113.83(12) . . ? N2 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N2 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C13 118.35(13) . . ? C6 C5 C4 119.58(13) . . ? C13 C5 C4 122.05(13) . . ? C5 C6 C7 120.89(15) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.04(15) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C12 C8 C7 119.60(15) . . ? C12 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C1 C9 C10 118.02(12) . . ? C1 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? C9 C10 C11 121.75(13) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? N1 C11 C10 120.78(14) . . ? N1 C11 C3 119.81(14) . . ? C10 C11 C3 119.41(12) . . ? C8 C12 C13 120.43(15) . . ? C8 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C5 C13 C12 120.68(14) . . ? C5 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.147 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.033 data_3 _database_code_depnum_ccdc_archive 'CCDC 867103' #TrackingRef '3.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N4 O2' _chemical_formula_sum 'C12 H12 N4 O2' _chemical_formula_weight 244.26 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 15.007(13) _cell_length_b 10.891(9) _cell_length_c 16.137(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.279(10) _cell_angle_gamma 90.00 _cell_volume 2404(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.995 _cell_measurement_theta_max 0.998 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 2.39 _exptl_absorpt_correction_T_max 26.46 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 8321 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.46 _reflns_number_total 2289 _reflns_number_gt 1235 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0643P)^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 2289 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 N4 N 1.06767(14) 0.98955(18) 0.18641(12) 0.0601(5) Uani 1 1 d . . . O1 O 0.80664(15) 0.34825(17) -0.05325(11) 0.0869(6) Uani 1 1 d . . . C13 C 0.98376(16) 1.0093(2) 0.11266(14) 0.0501(6) Uani 1 1 d . . . N2 N 0.89212(15) 0.83502(19) 0.13177(13) 0.0563(6) Uani 1 1 d . . . O2 O 0.85182(16) 0.51167(17) -0.09978(12) 0.0939(7) Uani 1 1 d . . . N1 N 0.86093(16) 0.7105(2) 0.26806(14) 0.0644(6) Uani 1 1 d . . . C1 C 1.0968(2) 1.2052(3) 0.19316(19) 0.0767(8) Uani 1 1 d . . . H1 H 1.1377 1.2706 0.2218 0.092 Uiso 1 1 calc R . . C2 C 1.12123(19) 1.0885(3) 0.22494(17) 0.0724(8) Uani 1 1 d . . . H2 H 1.1788 1.0770 0.2767 0.087 Uiso 1 1 calc R . . C3 C 0.92664(17) 0.8952(2) 0.07024(14) 0.0576(6) Uani 1 1 d . . . H3A H 0.8712 0.9167 0.0145 0.069 Uiso 1 1 calc R . . H3B H 0.9678 0.8391 0.0550 0.069 Uiso 1 1 calc R . . C4 C 0.86890(14) 0.71111(19) 0.12116(13) 0.0455(5) Uani 1 1 d . . . C5 C 0.85997(15) 0.6458(2) 0.04444(13) 0.0500(6) Uani 1 1 d . . . H5 H 0.8692 0.6856 -0.0025 0.060 Uiso 1 1 calc R . . C6 C 0.83741(16) 0.5217(2) 0.03709(13) 0.0515(6) Uani 1 1 d . . . N3 N 0.83168(15) 0.4569(2) -0.04266(12) 0.0643(6) Uani 1 1 d . . . C8 C 1.0115(2) 1.2244(2) 0.1187(2) 0.0737(8) Uani 1 1 d . . . H8 H 0.9929 1.3033 0.0960 0.088 Uiso 1 1 calc R . . C9 C 0.95321(17) 1.1244(2) 0.07769(16) 0.0610(7) Uani 1 1 d . . . H9 H 0.8943 1.1349 0.0273 0.073 Uiso 1 1 calc R . . C10 C 0.85352(15) 0.6478(2) 0.19175(13) 0.0493(6) Uani 1 1 d . . . C11 C 0.83002(17) 0.5240(2) 0.18099(14) 0.0617(7) Uani 1 1 d . . . H11 H 0.8193 0.4833 0.2267 0.074 Uiso 1 1 calc R . . C12 C 0.82203(18) 0.4592(2) 0.10474(15) 0.0620(7) Uani 1 1 d . . . H12 H 0.8068 0.3760 0.0990 0.074 Uiso 1 1 calc R . . H2A H 0.9111(17) 0.864(2) 0.1805(16) 0.068(8) Uiso 1 1 d . . . H1A H 0.8557(18) 0.670(2) 0.3083(17) 0.082(9) Uiso 1 1 d . . . H1B H 0.881(2) 0.798(3) 0.2778(19) 0.122(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 N4 0.0659(13) 0.0607(14) 0.0522(11) 0.0038(9) 0.0228(11) -0.0063(10) O1 0.1360(17) 0.0567(12) 0.0620(11) -0.0159(9) 0.0346(11) -0.0096(11) C13 0.0577(14) 0.0569(16) 0.0429(12) 0.0028(10) 0.0279(11) -0.0049(11) N2 0.0802(14) 0.0540(14) 0.0454(12) -0.0075(10) 0.0365(11) -0.0169(10) O2 0.1513(19) 0.0910(15) 0.0618(11) -0.0202(10) 0.0666(13) -0.0284(12) N1 0.0964(17) 0.0618(16) 0.0458(12) -0.0041(10) 0.0403(11) -0.0156(12) C1 0.094(2) 0.063(2) 0.0805(19) -0.0134(15) 0.0435(17) -0.0228(16) C2 0.0717(18) 0.075(2) 0.0624(16) -0.0012(14) 0.0193(14) -0.0143(15) C3 0.0708(16) 0.0604(16) 0.0472(13) 0.0017(11) 0.0297(12) -0.0120(12) C4 0.0508(13) 0.0468(14) 0.0405(12) 0.0000(9) 0.0202(10) -0.0044(10) C5 0.0596(14) 0.0563(16) 0.0379(12) 0.0015(10) 0.0240(10) -0.0033(11) C6 0.0655(15) 0.0507(15) 0.0379(12) -0.0057(10) 0.0208(11) -0.0019(11) N3 0.0839(15) 0.0617(15) 0.0458(12) -0.0108(10) 0.0250(11) -0.0041(11) C8 0.093(2) 0.0489(17) 0.091(2) 0.0086(14) 0.0504(18) 0.0018(15) C9 0.0654(16) 0.0596(17) 0.0619(15) 0.0124(12) 0.0301(13) 0.0006(13) C10 0.0588(14) 0.0531(15) 0.0389(12) -0.0014(10) 0.0231(11) -0.0063(11) C11 0.0894(18) 0.0565(17) 0.0462(13) 0.0048(11) 0.0350(13) -0.0087(13) C12 0.0878(18) 0.0490(15) 0.0507(13) 0.0002(11) 0.0300(13) -0.0040(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 N4 C2 1.335(3) . ? N4 C13 1.348(3) . ? O1 N3 1.232(3) . ? C13 C9 1.374(3) . ? C13 C3 1.505(3) . ? N2 C4 1.387(3) . ? N2 C3 1.451(3) . ? N2 H2A 0.79(2) . ? O2 N3 1.235(2) . ? N1 C10 1.372(3) . ? N1 H1A 0.82(3) . ? N1 H1B 0.99(3) . ? C1 C2 1.363(4) . ? C1 C8 1.365(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.385(3) . ? C4 C10 1.429(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C12 1.384(3) . ? C6 N3 1.439(3) . ? C8 C9 1.383(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.387(3) . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 N4 C13 116.6(2) . . ? N4 C13 C9 122.8(2) . . ? N4 C13 C3 114.9(2) . . ? C9 C13 C3 122.4(2) . . ? C4 N2 C3 119.82(19) . . ? C4 N2 H2A 119.3(17) . . ? C3 N2 H2A 114.6(18) . . ? C10 N1 H1A 116.3(19) . . ? C10 N1 H1B 121.7(18) . . ? H1A N1 H1B 121(2) . . ? C2 C1 C8 119.0(2) . . ? C2 C1 H1 120.5 . . ? C8 C1 H1 120.5 . . ? N4 C2 C1 124.1(3) . . ? N4 C2 H2 118.0 . . ? C1 C2 H2 118.0 . . ? N2 C3 C13 111.00(18) . . ? N2 C3 H3A 109.4 . . ? C13 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? C13 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 N2 122.45(19) . . ? C5 C4 C10 118.5(2) . . ? N2 C4 C10 119.06(19) . . ? C4 C5 C6 120.46(19) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C12 C6 C5 121.7(2) . . ? C12 C6 N3 119.8(2) . . ? C5 C6 N3 118.49(19) . . ? O1 N3 O2 121.0(2) . . ? O1 N3 C6 119.8(2) . . ? O2 N3 C6 119.2(2) . . ? C1 C8 C9 118.7(2) . . ? C1 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C13 C9 C8 118.9(2) . . ? C13 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? N1 C10 C11 121.2(2) . . ? N1 C10 C4 119.7(2) . . ? C11 C10 C4 119.04(19) . . ? C12 C11 C10 122.2(2) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C6 118.1(2) . . ? C11 C12 H12 121.0 . . ? C6 C12 H12 121.0 . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.132 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.047 data_3.H2PO4- _database_code_depnum_ccdc_archive 'CCDC 867417' #TrackingRef '3.H2PO4-.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N4 O2, C16 H36 N,H2 O4 P, H2 O' _chemical_formula_sum 'C28 H52 N5 O7 P' _chemical_formula_weight 601.72 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' P P 0.1023 0.0942 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.602(5) _cell_length_b 13.194(5) _cell_length_c 15.104(5) _cell_angle_alpha 113.014(5) _cell_angle_beta 94.332(5) _cell_angle_gamma 105.702(5) _cell_volume 1659.6(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 26.40 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 20066 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.40 _reflns_number_total 6579 _reflns_number_gt 5090 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0863P)^2^+0.5845P] 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 6579 _refine_ls_number_parameters 398 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 1.045 _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 P001 P 0.68440(6) 0.44455(5) 0.46652(4) 0.04699(18) Uani 1 1 d . . . O7 O 0.78571(18) 0.39398(15) 0.50200(11) 0.0588(4) Uani 1 1 d . . . O6 O 0.69438(16) 0.56534(14) 0.53715(12) 0.0606(4) Uani 1 1 d . . . O3 O 0.9923(2) 0.4601(2) 0.34081(15) 0.0672(5) Uani 1 1 d . . . O4 O 0.7175(2) 0.4454(2) 0.36670(13) 0.0741(6) Uani 1 1 d . . . O5 O 0.5233(2) 0.36109(15) 0.43753(16) 0.0761(6) Uani 1 1 d . . . N5 N 0.53968(19) 0.43867(15) 0.76685(12) 0.0471(4) Uani 1 1 d . . . N1 N 0.0024(3) -0.26647(18) 0.58640(17) 0.0622(5) Uani 1 1 d . . . N2 N 0.3049(2) -0.1503(2) 0.65242(17) 0.0644(6) Uani 1 1 d . . . O1 O 0.1161(3) 0.24428(19) 0.90051(16) 0.0968(7) Uani 1 1 d . . . O2 O 0.3386(3) 0.23786(16) 0.90992(14) 0.0821(6) Uani 1 1 d . . . C16 C 0.4614(2) 0.4728(2) 0.85212(15) 0.0512(5) Uani 1 1 d . . . H16A H 0.4160 0.4037 0.8619 0.061 Uiso 1 1 calc R . . H16B H 0.5353 0.5275 0.9110 0.061 Uiso 1 1 calc R . . C7 C 0.2075(2) -0.09359(18) 0.68981(16) 0.0492(5) Uani 1 1 d . . . C24 C 0.6449(2) 0.3816(2) 0.79172(16) 0.0538(5) Uani 1 1 d . . . H24A H 0.7114 0.4367 0.8538 0.065 Uiso 1 1 calc R . . H24B H 0.5877 0.3152 0.8012 0.065 Uiso 1 1 calc R . . C25 C 0.4308(3) 0.3558(2) 0.67056(15) 0.0541(5) Uani 1 1 d . . . H25A H 0.3666 0.3956 0.6568 0.065 Uiso 1 1 calc R . . H25B H 0.4858 0.3383 0.6183 0.065 Uiso 1 1 calc R . . C20 C 0.6228(2) 0.54496(19) 0.75203(15) 0.0504(5) Uani 1 1 d . . . H20A H 0.6644 0.5187 0.6939 0.061 Uiso 1 1 calc R . . H20B H 0.5521 0.5804 0.7391 0.061 Uiso 1 1 calc R . . N3 N 0.2048(3) 0.19194(18) 0.87369(15) 0.0675(6) Uani 1 1 d . . . C8 C 0.0530(2) -0.15251(18) 0.65321(15) 0.0486(5) Uani 1 1 d . . . C11 C 0.1514(3) 0.07422(19) 0.79739(16) 0.0536(5) Uani 1 1 d . . . C12 C 0.2542(3) 0.01921(19) 0.76344(16) 0.0528(5) Uani 1 1 d . . . H12 H 0.3544 0.0582 0.7902 0.063 Uiso 1 1 calc R . . C9 C -0.0453(3) -0.0933(2) 0.68898(17) 0.0554(5) Uani 1 1 d . . . H9 H -0.1461 -0.1314 0.6640 0.066 Uiso 1 1 calc R . . C10 C 0.0022(3) 0.0202(2) 0.76031(18) 0.0588(6) Uani 1 1 d . . . H10 H -0.0648 0.0589 0.7826 0.071 Uiso 1 1 calc R . . C1 C 0.5289(2) -0.0754(2) 0.78365(19) 0.0622(6) Uani 1 1 d . . . N4 N 0.6525(3) 0.0166(2) 0.82845(19) 0.0853(7) Uani 1 1 d . . . C15 C 0.3441(3) 0.5264(2) 0.84245(17) 0.0616(6) Uani 1 1 d . . . H15A H 0.2672 0.4720 0.7851 0.074 Uiso 1 1 calc R . . H15B H 0.3873 0.5963 0.8335 0.074 Uiso 1 1 calc R . . C19 C 0.7457(3) 0.6377(2) 0.83635(17) 0.0611(6) Uani 1 1 d . . . H19A H 0.8185 0.6042 0.8498 0.073 Uiso 1 1 calc R . . H19B H 0.7058 0.6666 0.8949 0.073 Uiso 1 1 calc R . . C6 C 0.4634(3) -0.0943(2) 0.68227(19) 0.0652(6) Uani 1 1 d . . . H6A H 0.4876 -0.0194 0.6797 0.078 Uiso 1 1 calc R . . H6B H 0.5097 -0.1414 0.6352 0.078 Uiso 1 1 calc R . . C18 C 0.8190(3) 0.7375(2) 0.81155(18) 0.0575(5) Uani 1 1 d . . . H18A H 0.8484 0.7068 0.7489 0.069 Uiso 1 1 calc R . . H18B H 0.7483 0.7757 0.8049 0.069 Uiso 1 1 calc R . . C23 C 0.7368(3) 0.3406(3) 0.7167(2) 0.0683(7) Uani 1 1 d . . . H23A H 0.6718 0.2868 0.6538 0.082 Uiso 1 1 calc R . . H23B H 0.7987 0.4069 0.7090 0.082 Uiso 1 1 calc R . . C14 C 0.2776(3) 0.5566(3) 0.93303(19) 0.0731(7) Uani 1 1 d . . . H14A H 0.3553 0.6106 0.9900 0.088 Uiso 1 1 calc R . . H14B H 0.2355 0.4864 0.9418 0.088 Uiso 1 1 calc R . . C26 C 0.3354(3) 0.2421(2) 0.6677(2) 0.0804(8) Uani 1 1 d . . . H26A H 0.2694 0.2573 0.7132 0.096 Uiso 1 1 calc R . . H26B H 0.3975 0.2047 0.6878 0.096 Uiso 1 1 calc R . . C29 C 0.4706(3) -0.1480(3) 0.8257(2) 0.0726(7) Uani 1 1 d . . . H29 H 0.3848 -0.2114 0.7929 0.087 Uiso 1 1 calc R . . C22 C 0.8327(4) 0.2815(3) 0.7463(3) 0.0858(9) Uani 1 1 d . . . H22A H 0.7704 0.2118 0.7490 0.103 Uiso 1 1 calc R . . H22B H 0.8920 0.3332 0.8116 0.103 Uiso 1 1 calc R . . C5 C 0.5415(4) -0.1255(3) 0.9176(2) 0.0845(8) Uani 1 1 d . . . H5 H 0.5034 -0.1734 0.9477 0.101 Uiso 1 1 calc R . . C4 C 0.6667(4) -0.0335(4) 0.9637(2) 0.0926(10) Uani 1 1 d . . . H4 H 0.7159 -0.0167 1.0258 0.111 Uiso 1 1 calc R . . C17 C 0.9526(3) 0.8256(3) 0.8888(2) 0.0824(8) Uani 1 1 d . . . H17A H 0.9952 0.8873 0.8704 0.124 Uiso 1 1 calc R . . H17B H 1.0241 0.7886 0.8945 0.124 Uiso 1 1 calc R . . H17C H 0.9239 0.8571 0.9507 0.124 Uiso 1 1 calc R . . C21 C 0.9335(4) 0.2488(4) 0.6761(3) 0.1098(12) Uani 1 1 d . . . H21A H 0.9929 0.2118 0.6980 0.165 Uiso 1 1 calc R . . H21B H 0.9965 0.3176 0.6739 0.165 Uiso 1 1 calc R . . H21C H 0.8753 0.1960 0.6116 0.165 Uiso 1 1 calc R . . C27 C 0.2457(4) 0.1620(3) 0.5646(3) 0.1084(13) Uani 1 1 d D . . H27A H 0.1426 0.1388 0.5692 0.130 Uiso 1 1 calc R . . H27B H 0.2555 0.2074 0.5267 0.130 Uiso 1 1 calc R . . C13 C 0.1587(4) 0.6107(4) 0.9274(3) 0.1055(11) Uani 1 1 d . . . H13A H 0.1202 0.6281 0.9866 0.158 Uiso 1 1 calc R . . H13B H 0.0803 0.5571 0.8720 0.158 Uiso 1 1 calc R . . H13C H 0.2001 0.6813 0.9203 0.158 Uiso 1 1 calc R . . C3 C 0.7184(4) 0.0337(3) 0.9169(3) 0.0994(11) Uani 1 1 d . . . H3 H 0.8057 0.0960 0.9483 0.119 Uiso 1 1 calc R . . C28 C 0.2746(15) 0.0711(7) 0.5162(4) 0.378(10) Uani 1 1 d D . . H28A H 0.2085 0.0290 0.4532 0.567 Uiso 1 1 calc R . . H28B H 0.2627 0.0232 0.5511 0.567 Uiso 1 1 calc R . . H28C H 0.3746 0.0917 0.5073 0.567 Uiso 1 1 calc R . . H1A H -0.092(4) -0.301(3) 0.566(2) 0.079(9) Uiso 1 1 d . . . H1B H 0.063(3) -0.294(2) 0.557(2) 0.068(8) Uiso 1 1 d . . . H2A H 0.274(3) -0.216(2) 0.6051(19) 0.058(7) Uiso 1 1 d . . . H3B H 1.060(4) 0.508(3) 0.391(2) 0.082(10) Uiso 1 1 d . . . H4A H 0.808(4) 0.455(3) 0.363(2) 0.092(11) Uiso 1 1 d . . . H3A H 0.984(5) 0.392(4) 0.332(3) 0.132(17) Uiso 1 1 d . . . H5A H 0.448(5) 0.389(3) 0.446(3) 0.123(14) 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 P001 0.0424(3) 0.0539(3) 0.0430(3) 0.0164(3) 0.0080(2) 0.0200(2) O7 0.0622(9) 0.0718(11) 0.0524(9) 0.0294(8) 0.0114(7) 0.0328(8) O6 0.0450(8) 0.0533(9) 0.0666(10) 0.0100(8) 0.0072(7) 0.0151(7) O3 0.0596(11) 0.0815(14) 0.0623(11) 0.0326(11) 0.0142(9) 0.0227(10) O4 0.0719(12) 0.1224(17) 0.0554(10) 0.0477(11) 0.0195(9) 0.0571(12) O5 0.0487(10) 0.0528(10) 0.1024(15) 0.0100(10) 0.0119(9) 0.0158(8) N5 0.0508(9) 0.0511(10) 0.0393(9) 0.0228(8) 0.0029(7) 0.0131(8) N1 0.0477(12) 0.0506(12) 0.0717(14) 0.0149(10) 0.0022(10) 0.0110(10) N2 0.0489(11) 0.0538(12) 0.0682(13) 0.0079(11) 0.0015(9) 0.0138(9) O1 0.135(2) 0.0697(13) 0.0828(14) 0.0164(11) 0.0174(13) 0.0544(14) O2 0.1011(16) 0.0549(11) 0.0656(11) 0.0156(9) 0.0035(11) 0.0074(10) C16 0.0562(12) 0.0567(13) 0.0400(10) 0.0233(10) 0.0084(9) 0.0138(10) C7 0.0520(12) 0.0464(12) 0.0493(11) 0.0227(10) 0.0064(9) 0.0139(9) C24 0.0550(12) 0.0602(13) 0.0518(12) 0.0321(11) 0.0034(9) 0.0171(10) C25 0.0597(13) 0.0569(13) 0.0394(11) 0.0172(10) -0.0023(9) 0.0180(10) C20 0.0580(12) 0.0524(12) 0.0444(11) 0.0266(10) 0.0090(9) 0.0149(10) N3 0.1018(18) 0.0500(12) 0.0505(11) 0.0230(10) 0.0118(12) 0.0231(12) C8 0.0508(11) 0.0467(12) 0.0500(11) 0.0253(10) 0.0046(9) 0.0129(9) C11 0.0727(15) 0.0438(12) 0.0476(12) 0.0239(10) 0.0111(10) 0.0176(10) C12 0.0557(12) 0.0469(12) 0.0522(12) 0.0239(10) 0.0036(10) 0.0095(10) C9 0.0520(12) 0.0568(14) 0.0624(13) 0.0308(12) 0.0083(10) 0.0183(10) C10 0.0706(15) 0.0587(14) 0.0606(14) 0.0324(12) 0.0195(11) 0.0297(12) C1 0.0432(12) 0.0606(14) 0.0673(15) 0.0120(12) 0.0084(10) 0.0174(11) N4 0.0552(13) 0.0835(16) 0.0841(17) 0.0181(13) 0.0003(12) 0.0031(12) C15 0.0706(15) 0.0706(16) 0.0463(12) 0.0249(12) 0.0102(11) 0.0278(12) C19 0.0634(14) 0.0620(14) 0.0533(13) 0.0294(11) 0.0022(10) 0.0088(11) C6 0.0497(13) 0.0629(15) 0.0706(16) 0.0199(13) 0.0120(11) 0.0132(11) C18 0.0577(13) 0.0546(13) 0.0581(13) 0.0240(11) 0.0106(10) 0.0155(10) C23 0.0722(16) 0.0813(18) 0.0667(15) 0.0392(14) 0.0159(12) 0.0365(14) C14 0.0798(18) 0.0872(19) 0.0579(15) 0.0316(14) 0.0210(13) 0.0332(15) C26 0.0824(19) 0.0559(15) 0.0815(19) 0.0236(14) -0.0198(15) 0.0089(13) C29 0.0604(15) 0.0667(16) 0.0801(18) 0.0243(14) 0.0088(13) 0.0173(12) C22 0.0819(19) 0.099(2) 0.111(2) 0.066(2) 0.0294(17) 0.0472(18) C5 0.087(2) 0.095(2) 0.0800(19) 0.0359(18) 0.0189(17) 0.0446(18) C4 0.080(2) 0.114(3) 0.0655(18) 0.0126(19) 0.0030(16) 0.046(2) C17 0.0732(17) 0.0678(17) 0.091(2) 0.0387(16) -0.0093(15) 0.0011(14) C21 0.107(3) 0.117(3) 0.148(3) 0.072(3) 0.050(2) 0.072(2) C27 0.088(2) 0.077(2) 0.100(3) -0.0071(19) -0.0257(19) 0.0168(18) C13 0.109(3) 0.128(3) 0.094(2) 0.039(2) 0.037(2) 0.068(2) C3 0.0666(18) 0.103(3) 0.081(2) 0.008(2) -0.0133(16) 0.0113(17) C28 0.81(3) 0.205(8) 0.082(4) -0.028(4) -0.095(8) 0.300(13) _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 P001 O7 1.4935(16) . ? P001 O6 1.5033(18) . ? P001 O5 1.5476(19) . ? P001 O4 1.5682(18) . ? O3 H3B 0.86(3) . ? O3 H3A 0.83(5) . ? O4 H4A 0.85(3) . ? O5 H5A 0.89(4) . ? N5 C24 1.518(3) . ? N5 C16 1.518(3) . ? N5 C25 1.520(3) . ? N5 C20 1.523(3) . ? N1 C8 1.364(3) . ? N1 H1A 0.86(3) . ? N1 H1B 0.83(3) . ? N2 C7 1.372(3) . ? N2 C6 1.446(3) . ? N2 H2A 0.83(3) . ? O1 N3 1.232(3) . ? O2 N3 1.237(3) . ? C16 C15 1.509(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C7 C12 1.386(3) . ? C7 C8 1.424(3) . ? C24 C23 1.512(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.514(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C20 C19 1.511(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? N3 C11 1.444(3) . ? C8 C9 1.393(3) . ? C11 C10 1.374(4) . ? C11 C12 1.392(3) . ? C12 H12 0.9300 . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C1 N4 1.340(3) . ? C1 C29 1.368(4) . ? C1 C6 1.508(4) . ? N4 C3 1.340(4) . ? C15 C14 1.510(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C19 C18 1.515(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C18 C17 1.505(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C23 C22 1.501(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C14 C13 1.515(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C26 C27 1.517(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C29 C5 1.379(4) . ? C29 H29 0.9300 . ? C22 C21 1.507(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C5 C4 1.351(5) . ? C5 H5 0.9300 . ? C4 C3 1.355(5) . ? C4 H4 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C27 C28 1.255(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C3 H3 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 P001 O6 114.72(10) . . ? O7 P001 O5 109.79(11) . . ? O6 P001 O5 110.50(10) . . ? O7 P001 O4 108.68(9) . . ? O6 P001 O4 109.24(11) . . ? O5 P001 O4 103.29(12) . . ? H3B O3 H3A 110(4) . . ? P001 O4 H4A 113(2) . . ? P001 O5 H5A 121(3) . . ? C24 N5 C16 106.53(15) . . ? C24 N5 C25 110.84(17) . . ? C16 N5 C25 111.58(17) . . ? C24 N5 C20 111.08(17) . . ? C16 N5 C20 110.93(17) . . ? C25 N5 C20 105.96(15) . . ? C8 N1 H1A 118(2) . . ? C8 N1 H1B 117(2) . . ? H1A N1 H1B 122(3) . . ? C7 N2 C6 122.5(2) . . ? C7 N2 H2A 120.2(18) . . ? C6 N2 H2A 116.7(18) . . ? C15 C16 N5 116.70(17) . . ? C15 C16 H16A 108.1 . . ? N5 C16 H16A 108.1 . . ? C15 C16 H16B 108.1 . . ? N5 C16 H16B 108.1 . . ? H16A C16 H16B 107.3 . . ? N2 C7 C12 122.2(2) . . ? N2 C7 C8 119.3(2) . . ? C12 C7 C8 118.5(2) . . ? C23 C24 N5 116.08(18) . . ? C23 C24 H24A 108.3 . . ? N5 C24 H24A 108.3 . . ? C23 C24 H24B 108.3 . . ? N5 C24 H24B 108.3 . . ? H24A C24 H24B 107.4 . . ? C26 C25 N5 115.46(19) . . ? C26 C25 H25A 108.4 . . ? N5 C25 H25A 108.4 . . ? C26 C25 H25B 108.4 . . ? N5 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? C19 C20 N5 116.07(17) . . ? C19 C20 H20A 108.3 . . ? N5 C20 H20A 108.3 . . ? C19 C20 H20B 108.3 . . ? N5 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? O1 N3 O2 121.8(2) . . ? O1 N3 C11 119.1(3) . . ? O2 N3 C11 119.1(2) . . ? N1 C8 C9 120.7(2) . . ? N1 C8 C7 120.2(2) . . ? C9 C8 C7 119.1(2) . . ? C10 C11 C12 122.1(2) . . ? C10 C11 N3 119.6(2) . . ? C12 C11 N3 118.3(2) . . ? C7 C12 C11 120.1(2) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C10 C9 C8 122.1(2) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C11 C10 C9 118.0(2) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? N4 C1 C29 122.3(3) . . ? N4 C1 C6 114.5(2) . . ? C29 C1 C6 123.2(2) . . ? C3 N4 C1 116.6(3) . . ? C16 C15 C14 110.51(19) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C20 C19 C18 110.46(18) . . ? C20 C19 H19A 109.6 . . ? C18 C19 H19A 109.6 . . ? C20 C19 H19B 109.6 . . ? C18 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? N2 C6 C1 115.0(2) . . ? N2 C6 H6A 108.5 . . ? C1 C6 H6A 108.5 . . ? N2 C6 H6B 108.5 . . ? C1 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C17 C18 C19 112.2(2) . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C22 C23 C24 111.9(2) . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C15 C14 C13 112.9(2) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C25 C26 C27 110.1(3) . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26B 109.6 . . ? C27 C26 H26B 109.6 . . ? H26A C26 H26B 108.2 . . ? C1 C29 C5 118.8(3) . . ? C1 C29 H29 120.6 . . ? C5 C29 H29 120.6 . . ? C23 C22 C21 112.4(3) . . ? C23 C22 H22A 109.1 . . ? C21 C22 H22A 109.1 . . ? C23 C22 H22B 109.1 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? C4 C5 C29 119.7(3) . . ? C4 C5 H5 120.1 . . ? C29 C5 H5 120.1 . . ? C5 C4 C3 118.0(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C28 C27 C26 118.9(5) . . ? C28 C27 H27A 107.6 . . ? C26 C27 H27A 107.6 . . ? C28 C27 H27B 107.6 . . ? C26 C27 H27B 107.6 . . ? H27A C27 H27B 107.0 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C3 C4 124.5(3) . . ? N4 C3 H3 117.8 . . ? C4 C3 H3 117.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.704 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.042