# 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_exp_1345 #TrackingRef '18390_web_deposit_cif_file_2_QianTao_1362724506.exp_1345-SA-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common phenazopyridine _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N5, C7 H5 O3' _chemical_formula_sum 'C18 H17 N5 O3' _chemical_formula_weight 351.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2907(10) _cell_length_b 5.1776(4) _cell_length_c 25.343(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.038(6) _cell_angle_gamma 90.00 _cell_volume 1638.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1107 _cell_measurement_theta_min 2.3360 _cell_measurement_theta_max 70.7855 _exptl_crystal_description NEEDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 5434 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 66.48 _reflns_number_total 2829 _reflns_number_gt 2018 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0740P)^2^+0.0241P] 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 2829 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 N3 N 0.01766(15) -0.1039(4) 0.20386(9) 0.0328(5) Uani 1 1 d . . . N2 N 0.15687(14) 0.0108(3) 0.17446(7) 0.0239(4) Uani 1 1 d . . . C1 C 0.14579(18) 0.3536(4) 0.11021(9) 0.0264(5) Uani 1 1 d . . . C2 C 0.03957(19) 0.3931(4) 0.10773(10) 0.0309(5) Uani 1 1 d . . . H20 H -0.0007 0.5226 0.0846 0.037 Uiso 1 1 calc R . . C3 C -0.00598(18) 0.2482(5) 0.13802(10) 0.0311(5) Uani 1 1 d . . . H3C H -0.0763 0.2789 0.1358 0.037 Uiso 1 1 calc R . . C4 C 0.05427(18) 0.0501(4) 0.17303(9) 0.0269(5) Uani 1 1 d . . . C5 C 0.20445(18) 0.1554(4) 0.14544(9) 0.0242(5) Uani 1 1 d . . . C6 C 0.21074(19) 0.8066(4) 0.02246(9) 0.0306(5) Uani 1 1 d . . . C7 C 0.3134(2) 0.7349(5) 0.02507(10) 0.0357(6) Uani 1 1 d . . . H7 H 0.3464 0.5919 0.0461 0.043 Uiso 1 1 calc R . . C8 C 0.3662(2) 0.8767(5) -0.00366(11) 0.0388(6) Uani 1 1 d . . . H8 H 0.4348 0.8292 -0.0017 0.047 Uiso 1 1 calc R . . C9 C 0.3177(2) 1.0881(5) -0.03514(10) 0.0388(6) Uani 1 1 d . . . H9 H 0.3537 1.1840 -0.0541 0.047 Uiso 1 1 calc R . . C10 C 0.2153(2) 1.1571(5) -0.03841(11) 0.0405(6) Uani 1 1 d . . . H10 H 0.1823 1.2986 -0.0600 0.049 Uiso 1 1 calc R . . C11 C 0.1617(2) 1.0181(5) -0.00988(10) 0.0354(6) Uani 1 1 d . . . H11 H 0.0928 1.0658 -0.0123 0.043 Uiso 1 1 calc R . . N5 N 0.14942(16) 0.6723(4) 0.05030(8) 0.0318(5) Uani 1 1 d . . . N4 N 0.20205(16) 0.4953(3) 0.08248(7) 0.0289(4) Uani 1 1 d . . . N1 N 0.30607(14) 0.0994(4) 0.15149(8) 0.0300(5) Uani 1 1 d . . . H1B H 0.3385 -0.0247 0.1732 0.036 Uiso 1 1 d R . . H1A H 0.3389 0.1877 0.1336 0.036 Uiso 1 1 d R . . H2 H 0.1931 -0.1130 0.1950 0.036 Uiso 1 1 d R . . H3B H 0.0582 -0.2232 0.2239 0.036 Uiso 1 1 d R . . H3A H -0.0464 -0.0849 0.2041 0.036 Uiso 1 1 d R . . O1 O 0.15712(12) -0.4812(3) 0.26322(7) 0.0331(4) Uani 1 1 d . . . O2 O 0.29207(12) -0.3640(3) 0.23540(6) 0.0271(4) Uani 1 1 d . . . C12 C 0.25150(17) -0.5056(4) 0.26413(9) 0.0235(5) Uani 1 1 d . . . C13 C 0.32023(17) -0.7121(4) 0.30023(9) 0.0233(5) Uani 1 1 d . . . C14 C 0.42875(18) -0.7335(4) 0.30756(9) 0.0258(5) Uani 1 1 d . . . C15 C 0.49088(19) -0.9225(5) 0.34281(10) 0.0326(5) Uani 1 1 d . . . H26A H 0.5636 -0.9340 0.3482 0.039 Uiso 1 1 calc R . . C16 C 0.4452(2) -1.0926(5) 0.36969(10) 0.0341(6) Uani 1 1 d . . . H27A H 0.4873 -1.2187 0.3932 0.041 Uiso 1 1 calc R . . C17 C 0.3366(2) -1.0774(4) 0.36204(10) 0.0319(5) Uani 1 1 d . . . H28A H 0.3056 -1.1937 0.3799 0.038 Uiso 1 1 calc R . . C18 C 0.27586(19) -0.8883(4) 0.32777(9) 0.0285(5) Uani 1 1 d . . . H29A H 0.2033 -0.8773 0.3228 0.034 Uiso 1 1 calc R . . O3 O 0.47871(12) -0.5740(3) 0.28164(7) 0.0325(4) Uani 1 1 d . . . H4 H 0.4383 -0.4651 0.2644 0.049 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N3 0.0303(10) 0.0307(10) 0.0415(12) 0.0074(9) 0.0177(9) 0.0057(8) N2 0.0255(9) 0.0201(9) 0.0237(10) 0.0013(7) 0.0053(8) 0.0024(8) C1 0.0286(11) 0.0240(11) 0.0231(11) -0.0009(9) 0.0043(9) -0.0010(9) C2 0.0314(12) 0.0258(12) 0.0287(12) 0.0014(10) 0.0017(10) 0.0042(10) C3 0.0251(11) 0.0321(13) 0.0339(13) -0.0002(10) 0.0073(10) 0.0048(10) C4 0.0272(11) 0.0228(11) 0.0284(12) -0.0047(10) 0.0066(10) 0.0008(10) C5 0.0287(11) 0.0219(11) 0.0198(11) -0.0058(9) 0.0057(9) -0.0040(9) C6 0.0364(13) 0.0275(12) 0.0242(12) -0.0044(10) 0.0056(10) -0.0070(10) C7 0.0434(14) 0.0319(13) 0.0265(13) 0.0047(10) 0.0052(11) -0.0011(11) C8 0.0389(14) 0.0412(14) 0.0358(14) 0.0048(11) 0.0123(12) -0.0017(12) C9 0.0494(15) 0.0336(13) 0.0332(14) 0.0044(11) 0.0139(12) -0.0055(12) C10 0.0532(17) 0.0297(13) 0.0352(14) 0.0068(11) 0.0106(13) 0.0015(12) C11 0.0418(14) 0.0297(12) 0.0308(13) -0.0009(10) 0.0074(11) 0.0013(11) N5 0.0366(11) 0.0269(10) 0.0265(10) 0.0013(8) 0.0040(9) -0.0008(9) N4 0.0367(11) 0.0232(10) 0.0229(10) -0.0016(8) 0.0051(8) -0.0019(8) N1 0.0257(10) 0.0281(10) 0.0352(11) 0.0038(9) 0.0093(8) 0.0003(8) O1 0.0248(8) 0.0343(9) 0.0395(10) 0.0058(7) 0.0103(7) 0.0000(7) O2 0.0272(8) 0.0272(8) 0.0267(8) 0.0020(6) 0.0091(7) 0.0013(6) C12 0.0244(11) 0.0211(11) 0.0234(11) -0.0032(9) 0.0060(9) -0.0019(9) C13 0.0258(11) 0.0210(11) 0.0212(11) -0.0040(9) 0.0057(9) 0.0002(9) C14 0.0299(12) 0.0232(11) 0.0235(11) -0.0040(9) 0.0080(9) -0.0027(9) C15 0.0290(12) 0.0326(13) 0.0326(13) 0.0012(11) 0.0061(10) 0.0059(10) C16 0.0429(14) 0.0265(12) 0.0279(12) 0.0025(10) 0.0057(11) 0.0078(11) C17 0.0425(14) 0.0242(12) 0.0276(12) 0.0009(10) 0.0102(11) -0.0026(11) C18 0.0309(12) 0.0273(12) 0.0281(12) -0.0030(10) 0.0110(10) -0.0029(10) O3 0.0260(8) 0.0316(9) 0.0396(10) 0.0077(7) 0.0108(7) 0.0033(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 N3 C4 1.320(3) . ? N3 H3B 0.8614 . ? N3 H3A 0.8591 . ? N2 C5 1.349(3) . ? N2 C4 1.367(3) . ? N2 H2 0.8609 . ? C1 N4 1.397(3) . ? C1 C2 1.406(3) . ? C1 C5 1.408(3) . ? C2 C3 1.355(3) . ? C2 H20 0.9300 . ? C3 C4 1.412(3) . ? C3 H3C 0.9300 . ? C5 N1 1.338(3) . ? C6 C11 1.389(3) . ? C6 C7 1.394(4) . ? C6 N5 1.428(3) . ? C7 C8 1.382(3) . ? C7 H7 0.9300 . ? C8 C9 1.377(4) . ? C8 H8 0.9300 . ? C9 C10 1.381(4) . ? C9 H9 0.9300 . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N5 N4 1.266(3) . ? N1 H1B 0.8597 . ? N1 H1A 0.8599 . ? O1 C12 1.253(3) . ? O2 C12 1.276(3) . ? C12 C13 1.497(3) . ? C13 C14 1.394(3) . ? C13 C18 1.396(3) . ? C14 O3 1.361(3) . ? C14 C15 1.390(3) . ? C15 C16 1.375(4) . ? C15 H26A 0.9300 . ? C16 C17 1.392(4) . ? C16 H27A 0.9300 . ? C17 C18 1.372(3) . ? C17 H28A 0.9300 . ? C18 H29A 0.9300 . ? O3 H4 0.7977 . ? 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 C4 N3 H3B 119.9 . . ? C4 N3 H3A 120.2 . . ? H3B N3 H3A 119.9 . . ? C5 N2 C4 123.54(19) . . ? C5 N2 H2 118.3 . . ? C4 N2 H2 118.2 . . ? N4 C1 C2 127.1(2) . . ? N4 C1 C5 115.24(19) . . ? C2 C1 C5 117.6(2) . . ? C3 C2 C1 122.0(2) . . ? C3 C2 H20 119.0 . . ? C1 C2 H20 119.0 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3C 120.3 . . ? C4 C3 H3C 120.3 . . ? N3 C4 N2 117.4(2) . . ? N3 C4 C3 124.5(2) . . ? N2 C4 C3 118.1(2) . . ? N1 C5 N2 117.4(2) . . ? N1 C5 C1 123.3(2) . . ? N2 C5 C1 119.3(2) . . ? C11 C6 C7 119.5(2) . . ? C11 C6 N5 116.3(2) . . ? C7 C6 N5 124.2(2) . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.6(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 119.9(2) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? N4 N5 C6 112.82(19) . . ? N5 N4 C1 115.56(19) . . ? C5 N1 H1B 120.1 . . ? C5 N1 H1A 119.9 . . ? H1B N1 H1A 120.0 . . ? O1 C12 O2 123.2(2) . . ? O1 C12 C13 118.71(19) . . ? O2 C12 C13 118.07(18) . . ? C14 C13 C18 118.5(2) . . ? C14 C13 C12 121.66(19) . . ? C18 C13 C12 119.88(19) . . ? O3 C14 C15 117.2(2) . . ? O3 C14 C13 122.7(2) . . ? C15 C14 C13 120.1(2) . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H26A 119.9 . . ? C14 C15 H26A 119.9 . . ? C15 C16 C17 120.5(2) . . ? C15 C16 H27A 119.8 . . ? C17 C16 H27A 119.8 . . ? C18 C17 C16 119.0(2) . . ? C18 C17 H28A 120.5 . . ? C16 C17 H28A 120.5 . . ? C17 C18 C13 121.7(2) . . ? C17 C18 H29A 119.2 . . ? C13 C18 H29A 119.2 . . ? C14 O3 H4 110.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C3 -177.8(2) . . . . ? C5 C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C5 N2 C4 N3 -179.4(2) . . . . ? C5 N2 C4 C3 1.9(3) . . . . ? C2 C3 C4 N3 -179.3(2) . . . . ? C2 C3 C4 N2 -0.7(3) . . . . ? C4 N2 C5 N1 178.68(19) . . . . ? C4 N2 C5 C1 -2.0(3) . . . . ? N4 C1 C5 N1 -1.5(3) . . . . ? C2 C1 C5 N1 -179.8(2) . . . . ? N4 C1 C5 N2 179.15(18) . . . . ? C2 C1 C5 N2 0.9(3) . . . . ? C11 C6 C7 C8 1.1(4) . . . . ? N5 C6 C7 C8 179.6(2) . . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C6 0.0(4) . . . . ? C7 C6 C11 C10 -0.9(4) . . . . ? N5 C6 C11 C10 -179.6(2) . . . . ? C11 C6 N5 N4 -174.67(19) . . . . ? C7 C6 N5 N4 6.7(3) . . . . ? C6 N5 N4 C1 -178.92(18) . . . . ? C2 C1 N4 N5 -2.6(3) . . . . ? C5 C1 N4 N5 179.35(18) . . . . ? O1 C12 C13 C14 -173.5(2) . . . . ? O2 C12 C13 C14 7.0(3) . . . . ? O1 C12 C13 C18 6.1(3) . . . . ? O2 C12 C13 C18 -173.39(19) . . . . ? C18 C13 C14 O3 178.71(19) . . . . ? C12 C13 C14 O3 -1.7(3) . . . . ? C18 C13 C14 C15 -1.7(3) . . . . ? C12 C13 C14 C15 177.9(2) . . . . ? O3 C14 C15 C16 -179.1(2) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C14 C15 C16 C17 -0.1(4) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? C16 C17 C18 C13 0.4(3) . . . . ? C14 C13 C18 C17 0.9(3) . . . . ? C12 C13 C18 C17 -178.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B O2 0.86 2.57 3.253(2) 136.8 . N2 H2 O2 0.86 1.88 2.734(2) 169.7 . N3 H3B O1 0.86 1.90 2.758(2) 173.8 . O3 H4 O2 0.80 1.90 2.592(2) 144.4 . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 66.48 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.256 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 928350' ####################################################################### # # 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_tq_5_110618 #TrackingRef '18391_web_deposit_cif_file_3_QianTao_1362724506.tq_5_110618-SA-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common phenazopyridine _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N5, C7 H5 O3' _chemical_formula_sum 'C18 H17 N5 O3' _chemical_formula_weight 351.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.7841(2) _cell_length_b 9.3170(3) _cell_length_c 18.9162(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.498(2) _cell_angle_gamma 90.00 _cell_volume 842.36(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1107 _cell_measurement_theta_min 2.3360 _cell_measurement_theta_max 70.7855 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.809 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8883 _exptl_absorpt_correction_T_max 0.9235 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 3140 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 70.92 _reflns_number_total 2233 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0896P)^2^+0.0754P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(5) _refine_ls_number_reflns 2233 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1438 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.2674(6) 0.4495(4) 0.22366(15) 0.0621(7) Uani 1 1 d . . . N3 N 0.2617(7) 0.3673(5) 0.10983(16) 0.0778(9) Uani 1 1 d . . . H2 H 0.1331 0.5061 0.2105 0.093 Uiso 1 1 d R . . N1 N 0.2445(7) 0.5520(4) 0.33278(17) 0.0723(9) Uani 1 1 d . . . H1B H 0.1153 0.6071 0.3151 0.087 Uiso 1 1 d R . . H1A H 0.2969 0.5600 0.3767 0.087 Uiso 1 1 d R . . H3B H 0.1296 0.4273 0.0999 0.087 Uiso 1 1 d R . . H3A H 0.3227 0.3122 0.0773 0.087 Uiso 1 1 d R . . N4 N 0.6954(6) 0.3495(4) 0.38387(16) 0.0643(8) Uani 1 1 d . . . N5 N 0.6083(7) 0.4369(3) 0.42956(15) 0.0634(7) Uani 1 1 d . . . C15 C 0.3626(7) 0.4547(4) 0.29228(18) 0.0595(8) Uani 1 1 d . . . C16 C 0.5758(7) 0.3598(4) 0.31543(18) 0.0588(8) Uani 1 1 d . . . C17 C 0.6825(8) 0.2652(5) 0.2653(2) 0.0686(9) Uani 1 1 d . . . H17 H 0.8268 0.2004 0.2800 0.082 Uiso 1 1 calc R . . C18 C 0.5869(8) 0.2629(5) 0.19664(19) 0.0693(10) Uani 1 1 d . . . H18 H 0.6624 0.1976 0.1640 0.083 Uiso 1 1 calc R . . C19 C 0.3720(8) 0.3601(4) 0.17469(18) 0.0621(8) Uani 1 1 d . . . C20 C 0.7421(8) 0.4209(4) 0.49764(18) 0.0630(9) Uani 1 1 d . . . C21 C 0.6502(9) 0.5091(5) 0.5505(2) 0.0714(10) Uani 1 1 d . . . H21 H 0.5046 0.5762 0.5402 0.086 Uiso 1 1 calc R . . C22 C 0.7674(10) 0.5005(6) 0.6174(2) 0.0807(12) Uani 1 1 d . . . H22 H 0.7041 0.5628 0.6531 0.097 Uiso 1 1 calc R . . C23 C 0.9759(10) 0.4027(5) 0.6340(2) 0.0770(11) Uani 1 1 d . . . H23 H 1.0546 0.3964 0.6809 0.092 Uiso 1 1 calc R . . C24 C 1.0689(9) 0.3141(5) 0.5817(2) 0.0769(11) Uani 1 1 d . . . H24 H 1.2146 0.2473 0.5924 0.092 Uiso 1 1 calc R . . C25 C 0.9521(8) 0.3217(5) 0.51422(19) 0.0700(10) Uani 1 1 d . . . H25 H 1.0151 0.2590 0.4787 0.084 Uiso 1 1 calc R . . O1 O -0.1641(7) 0.6394(4) 0.21708(16) 0.0925(10) Uani 1 1 d . . . O2 O -0.1563(7) 0.5798(4) 0.10342(19) 0.0947(10) Uani 1 1 d . . . O3 O -0.4624(9) 0.7055(4) 0.01266(16) 0.1000(11) Uani 1 1 d . . . H4 H -0.3444 0.6492 0.0283 0.150 Uiso 1 1 d R . . C1 C -0.2439(8) 0.6545(5) 0.1547(2) 0.0718(11) Uani 1 1 d . . . C2 C -0.4687(7) 0.7629(5) 0.13637(18) 0.0620(9) Uani 1 1 d . . . C3 C -0.5636(8) 0.7823(5) 0.06639(17) 0.0684(10) Uani 1 1 d . . . C4 C -0.7673(11) 0.8866(6) 0.0500(2) 0.0865(13) Uani 1 1 d . . . H4A H -0.8308 0.9004 0.0022 0.104 Uiso 1 1 calc R . . C5 C -0.8745(11) 0.9679(6) 0.1016(3) 0.0862(12) Uani 1 1 d . . . H5A H -1.0117 1.0388 0.0898 0.103 Uiso 1 1 calc R . . C6 C -0.7854(11) 0.9480(6) 0.1704(3) 0.0879(12) Uani 1 1 d . . . H6A H -0.8624 1.0039 0.2068 0.105 Uiso 1 1 calc R . . C7 C -0.5865(9) 0.8481(5) 0.1868(2) 0.0737(11) Uani 1 1 d . . . H7A H -0.5258 0.8364 0.2350 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.0536(15) 0.0643(17) 0.0680(16) 0.0020(15) -0.0010(12) -0.0054(14) N3 0.076(2) 0.092(3) 0.0638(17) -0.0073(17) -0.0052(14) 0.0044(19) N1 0.0727(19) 0.072(2) 0.0717(18) -0.0055(16) -0.0005(14) 0.0120(17) N4 0.0615(16) 0.0625(18) 0.0686(16) 0.0011(15) 0.0008(13) -0.0002(15) N5 0.0653(16) 0.0634(18) 0.0615(15) 0.0005(14) 0.0036(12) -0.0001(15) C15 0.0541(17) 0.061(2) 0.0636(19) 0.0040(16) 0.0037(14) -0.0044(17) C16 0.0561(18) 0.0571(19) 0.0631(18) 0.0007(16) 0.0036(14) -0.0022(17) C17 0.065(2) 0.068(2) 0.073(2) 0.0020(19) 0.0045(16) 0.0053(19) C18 0.068(2) 0.067(2) 0.074(2) -0.0057(18) 0.0040(17) 0.0032(19) C19 0.0581(18) 0.066(2) 0.0628(18) -0.0003(16) 0.0060(14) -0.0076(17) C20 0.064(2) 0.065(2) 0.0604(18) 0.0055(17) 0.0035(15) -0.0082(18) C21 0.073(2) 0.068(2) 0.073(2) 0.0012(19) 0.0063(18) 0.003(2) C22 0.093(3) 0.083(3) 0.066(2) -0.009(2) 0.002(2) -0.005(3) C23 0.085(3) 0.081(3) 0.064(2) 0.0038(19) -0.0029(18) -0.012(2) C24 0.074(2) 0.079(3) 0.077(2) 0.014(2) 0.0003(18) 0.006(2) C25 0.072(2) 0.073(2) 0.066(2) 0.0004(18) 0.0080(16) 0.003(2) O1 0.0807(18) 0.106(3) 0.089(2) 0.0329(18) -0.0197(15) -0.0136(19) O2 0.087(2) 0.087(2) 0.111(2) 0.0035(19) 0.0083(17) 0.0109(19) O3 0.133(3) 0.102(2) 0.0657(17) 0.0042(16) 0.0060(16) 0.017(2) C1 0.065(2) 0.074(3) 0.075(2) 0.020(2) -0.0075(18) -0.019(2) C2 0.0539(17) 0.072(2) 0.0595(18) 0.0149(17) -0.0045(14) -0.0132(17) C3 0.073(2) 0.080(3) 0.0522(18) 0.0056(18) 0.0007(15) -0.007(2) C4 0.092(3) 0.097(3) 0.069(2) 0.024(2) -0.017(2) -0.006(3) C5 0.079(3) 0.077(3) 0.103(3) 0.007(2) 0.008(2) 0.006(2) C6 0.087(3) 0.081(3) 0.097(3) -0.001(2) 0.016(2) -0.001(3) C7 0.072(2) 0.084(3) 0.065(2) -0.0035(19) 0.0040(17) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C19 1.357(5) . ? N2 C15 1.358(4) . ? N3 C19 1.316(5) . ? N1 C15 1.329(5) . ? N4 N5 1.271(4) . ? N4 C16 1.396(5) . ? N5 C20 1.421(5) . ? C15 C16 1.406(5) . ? C16 C17 1.407(5) . ? C17 C18 1.358(5) . ? C18 C19 1.418(6) . ? C20 C21 1.380(6) . ? C20 C25 1.391(6) . ? C21 C22 1.365(6) . ? C22 C23 1.377(7) . ? C23 C24 1.377(6) . ? C24 C25 1.372(6) . ? O1 C1 1.233(5) . ? O2 C1 1.279(6) . ? O3 C3 1.350(5) . ? C1 C2 1.505(6) . ? C2 C7 1.381(6) . ? C2 C3 1.392(5) . ? C3 C4 1.401(7) . ? C4 C5 1.353(7) . ? C5 C6 1.365(7) . ? C6 C7 1.357(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 N2 C15 123.8(3) . . ? N5 N4 C16 117.0(3) . . ? N4 N5 C20 113.7(3) . . ? N1 C15 N2 116.3(3) . . ? N1 C15 C16 124.8(3) . . ? N2 C15 C16 118.9(3) . . ? N4 C16 C15 126.5(3) . . ? N4 C16 C17 115.8(3) . . ? C15 C16 C17 117.6(3) . . ? C18 C17 C16 122.5(4) . . ? C17 C18 C19 118.7(4) . . ? N3 C19 N2 117.4(4) . . ? N3 C19 C18 124.2(4) . . ? N2 C19 C18 118.4(3) . . ? C21 C20 C25 118.8(3) . . ? C21 C20 N5 116.7(4) . . ? C25 C20 N5 124.5(3) . . ? C22 C21 C20 120.4(4) . . ? C21 C22 C23 120.9(4) . . ? C22 C23 C24 119.1(4) . . ? C25 C24 C23 120.4(4) . . ? C24 C25 C20 120.3(4) . . ? O1 C1 O2 124.4(5) . . ? O1 C1 C2 119.1(4) . . ? O2 C1 C2 116.5(3) . . ? C7 C2 C3 117.2(4) . . ? C7 C2 C1 122.4(3) . . ? C3 C2 C1 120.4(4) . . ? O3 C3 C2 122.3(4) . . ? O3 C3 C4 118.1(3) . . ? C2 C3 C4 119.7(4) . . ? C5 C4 C3 120.7(4) . . ? C4 C5 C6 119.9(5) . . ? C7 C6 C5 119.9(5) . . ? C6 C7 C2 122.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N4 N5 C20 -179.3(3) . . . . ? C19 N2 C15 N1 177.6(3) . . . . ? C19 N2 C15 C16 -2.1(5) . . . . ? N5 N4 C16 C15 -1.9(5) . . . . ? N5 N4 C16 C17 177.9(3) . . . . ? N1 C15 C16 N4 1.1(6) . . . . ? N2 C15 C16 N4 -179.2(3) . . . . ? N1 C15 C16 C17 -178.7(4) . . . . ? N2 C15 C16 C17 1.0(5) . . . . ? N4 C16 C17 C18 -179.9(4) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C19 0.2(6) . . . . ? C15 N2 C19 N3 -179.3(3) . . . . ? C15 N2 C19 C18 2.2(5) . . . . ? C17 C18 C19 N3 -179.6(4) . . . . ? C17 C18 C19 N2 -1.2(6) . . . . ? N4 N5 C20 C21 -177.7(3) . . . . ? N4 N5 C20 C25 1.0(5) . . . . ? C25 C20 C21 C22 1.1(6) . . . . ? N5 C20 C21 C22 179.9(4) . . . . ? C20 C21 C22 C23 -1.0(7) . . . . ? C21 C22 C23 C24 0.9(7) . . . . ? C22 C23 C24 C25 -1.0(7) . . . . ? C23 C24 C25 C20 1.2(7) . . . . ? C21 C20 C25 C24 -1.3(6) . . . . ? N5 C20 C25 C24 -179.9(4) . . . . ? O1 C1 C2 C7 1.1(5) . . . . ? O2 C1 C2 C7 178.5(4) . . . . ? O1 C1 C2 C3 -179.9(4) . . . . ? O2 C1 C2 C3 -2.5(5) . . . . ? C7 C2 C3 O3 179.7(4) . . . . ? C1 C2 C3 O3 0.6(6) . . . . ? C7 C2 C3 C4 0.9(6) . . . . ? C1 C2 C3 C4 -178.2(4) . . . . ? O3 C3 C4 C5 -179.3(5) . . . . ? C2 C3 C4 C5 -0.6(7) . . . . ? C3 C4 C5 C6 -0.4(8) . . . . ? C4 C5 C6 C7 1.0(8) . . . . ? C5 C6 C7 C2 -0.6(7) . . . . ? C3 C2 C7 C6 -0.4(6) . . . . ? C1 C2 C7 C6 178.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.86 1.90 2.717(5) 159.3 . N1 H1B O1 0.86 2.26 2.983(4) 142.1 . N3 H3B O2 0.86 1.98 2.813(5) 164.9 . N3 H3A O3 0.86 2.11 2.959(5) 171.0 2_545 O3 H4 O2 0.82 1.77 2.499(5) 147.6 . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 70.92 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.320 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 928351' ####################################################################### # # 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_5 #TrackingRef '18392_web_deposit_cif_file_4_QianTao_1362724506.5-PAP-H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common phenazopyridine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N5 O4' _chemical_formula_weight 369.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.8924(7) _cell_length_b 5.13320(10) _cell_length_c 13.0371(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.854(3) _cell_angle_gamma 90.00 _cell_volume 1767.50(8) _cell_formula_units_Z 34 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 1.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 3400 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 70.94 _reflns_number_total 2506 _reflns_number_gt 2142 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0520P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.6(3) _refine_ls_number_reflns 2506 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.105 _refine_ls_shift/su_mean 0.007 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 N2 N 0.83878(8) -0.1088(5) 0.83146(17) 0.0297(5) Uani 1 1 d . . . N5 N 0.69909(9) -0.0056(5) 0.63715(17) 0.0340(6) Uani 1 1 d . . . N4 N 0.73532(9) 0.1482(5) 0.62875(17) 0.0337(6) Uani 1 1 d . . . C1 C 0.82010(11) 0.2788(6) 0.6864(2) 0.0338(6) Uani 1 1 d . . . C2 C 0.78085(10) 0.1072(6) 0.6960(2) 0.0302(6) Uani 1 1 d . . . C3 C 0.79108(10) -0.0940(6) 0.7724(2) 0.0294(6) Uani 1 1 d . . . N3 N 0.92233(9) 0.0150(5) 0.87961(19) 0.0357(6) Uani 1 1 d . . . N1 N 0.75687(9) -0.2659(5) 0.78983(19) 0.0336(5) Uani 1 1 d . . . C6 C 0.59828(12) 0.2607(7) 0.4271(2) 0.0414(7) Uani 1 1 d . . . C7 C 0.61532(11) -0.1386(7) 0.5704(2) 0.0380(7) Uani 1 1 d . . . C8 C 0.87690(10) 0.0569(6) 0.8204(2) 0.0304(6) Uani 1 1 d . . . C10 C 0.64450(11) 0.2433(6) 0.4937(2) 0.0351(6) Uani 1 1 d . . . C11 C 0.65317(10) 0.0402(6) 0.56572(19) 0.0320(6) Uani 1 1 d . . . C15 C 0.56041(12) 0.0810(7) 0.4307(2) 0.0408(7) Uani 1 1 d . . . C16 C 0.86727(11) 0.2599(6) 0.7464(2) 0.0348(6) Uani 1 1 d . . . C18 C 0.56915(11) -0.1212(7) 0.5027(2) 0.0413(7) Uani 1 1 d . . . H1 H 0.8118(10) 0.416(7) 0.626(2) 0.031(8) Uiso 1 1 d . . . H2 H 0.6204(11) -0.286(8) 0.624(2) 0.036(8) Uiso 1 1 d . . . H3B H 0.9290(12) -0.140(8) 0.931(2) 0.045(9) Uiso 1 1 d . . . H6 H 0.6698(13) 0.366(10) 0.494(3) 0.056(11) Uiso 1 1 d . . . H8 H 0.5906(13) 0.395(9) 0.376(3) 0.049(10) Uiso 1 1 d . . . H1B H 0.7637(13) -0.398(9) 0.849(3) 0.054(10) Uiso 1 1 d . . . H10 H 0.5426(13) -0.248(9) 0.507(3) 0.053(10) Uiso 1 1 d . . . H2 H 0.8434(12) -0.250(8) 0.885(3) 0.049(10) Uiso 1 1 d . . . H13 H 0.8951(13) 0.384(10) 0.741(3) 0.056(10) Uiso 1 1 d . . . H3B H 0.9472(14) 0.115(9) 0.872(3) 0.051(10) Uiso 1 1 d . . . H15 H 0.5273(13) 0.092(8) 0.382(2) 0.047(9) Uiso 1 1 d . . . H1A H 0.7226(15) -0.252(10) 0.743(3) 0.066(12) Uiso 1 1 d . . . O1 O 0.85864(7) -0.4961(4) 0.97893(15) 0.0342(5) Uani 1 1 d . . . O3 O 0.99945(7) -0.6254(4) 1.16376(16) 0.0376(5) Uani 1 1 d . . . H3 H 0.9910 -0.5270 1.1140 0.056 Uiso 1 1 calc R . . O2 O 0.94059(7) -0.4020(4) 1.01744(15) 0.0358(5) Uani 1 1 d . . . C4 C 0.91086(10) -0.7358(6) 1.1149(2) 0.0294(6) Uani 1 1 d . . . C5 C 0.95891(10) -0.7729(6) 1.1770(2) 0.0311(6) Uani 1 1 d . . . C9 C 0.87186(11) -0.9029(6) 1.1312(2) 0.0336(6) Uani 1 1 d . . . C12 C 0.90247(10) -0.5305(6) 1.0320(2) 0.0294(6) Uani 1 1 d . . . C13 C 0.96656(11) -0.9634(7) 1.2537(2) 0.0376(7) Uani 1 1 d . . . C14 C 0.92760(12) -1.1251(7) 1.2683(2) 0.0389(7) Uani 1 1 d . . . C17 C 0.87962(11) -1.0942(7) 1.2067(2) 0.0386(7) Uani 1 1 d . . . H4A H 0.8494(13) -1.200(8) 1.212(3) 0.053(10) Uiso 1 1 d . . . H5A H 0.8377(12) -0.879(8) 1.086(2) 0.046(9) Uiso 1 1 d . . . H7A H 0.9999(12) -0.988(8) 1.298(2) 0.045(9) Uiso 1 1 d . . . H11A H 0.9326(11) -1.255(7) 1.326(2) 0.035(8) Uiso 1 1 d . . . O4 O 0.76237(8) -0.6172(5) 0.96201(17) 0.0406(5) Uani 1 1 d . . . H4B H 0.7985(17) -0.604(11) 0.976(3) 0.072(12) Uiso 1 1 d . . . H4A H 0.7538(19) -0.775(13) 0.978(4) 0.084(16) 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 N2 0.0292(11) 0.0268(12) 0.0328(12) 0.0008(11) 0.0050(9) 0.0008(10) N5 0.0367(12) 0.0330(14) 0.0323(12) 0.0034(10) 0.0064(10) 0.0021(11) N4 0.0356(12) 0.0349(14) 0.0311(12) 0.0011(10) 0.0078(10) 0.0035(11) C1 0.0426(15) 0.0285(15) 0.0323(14) 0.0040(12) 0.0120(12) 0.0034(13) C2 0.0343(13) 0.0288(15) 0.0279(13) 0.0000(11) 0.0066(11) 0.0034(12) C3 0.0311(13) 0.0268(14) 0.0305(13) -0.0014(12) 0.0060(10) 0.0030(12) N3 0.0307(12) 0.0332(14) 0.0426(13) 0.0016(12) 0.0052(10) -0.0010(11) N1 0.0294(11) 0.0334(13) 0.0360(12) 0.0050(11) 0.0009(10) -0.0020(11) C6 0.0479(17) 0.0377(17) 0.0371(15) 0.0066(14) 0.0041(13) 0.0089(15) C7 0.0380(15) 0.0362(16) 0.0382(15) 0.0049(14) 0.0032(12) 0.0031(14) C8 0.0320(13) 0.0265(14) 0.0336(13) -0.0017(12) 0.0090(11) 0.0030(12) C10 0.0401(16) 0.0294(16) 0.0350(15) -0.0001(13) 0.0051(12) 0.0031(14) C11 0.0358(14) 0.0326(15) 0.0274(13) -0.0031(12) 0.0050(11) 0.0069(13) C15 0.0388(15) 0.0414(18) 0.0388(16) -0.0033(14) -0.0016(13) 0.0103(14) C16 0.0350(14) 0.0305(15) 0.0401(16) 0.0014(13) 0.0103(12) -0.0019(13) C18 0.0394(15) 0.0357(16) 0.0465(17) -0.0005(15) 0.0025(13) 0.0017(15) O1 0.0295(9) 0.0344(11) 0.0362(10) 0.0091(9) 0.0000(8) 0.0008(8) O3 0.0295(10) 0.0363(11) 0.0447(11) 0.0070(10) 0.0013(8) 0.0008(10) O2 0.0294(9) 0.0356(11) 0.0415(11) 0.0105(9) 0.0045(8) 0.0006(9) C4 0.0319(13) 0.0258(13) 0.0307(13) -0.0004(11) 0.0060(11) 0.0018(11) C5 0.0278(13) 0.0298(15) 0.0352(14) -0.0007(13) 0.0049(11) 0.0030(12) C9 0.0336(14) 0.0320(16) 0.0348(15) 0.0015(13) 0.0055(12) 0.0031(13) C12 0.0294(13) 0.0276(14) 0.0315(13) -0.0014(11) 0.0065(11) -0.0002(11) C13 0.0395(15) 0.0373(17) 0.0343(14) 0.0022(13) 0.0029(12) 0.0119(14) C14 0.0458(16) 0.0352(16) 0.0364(15) 0.0099(14) 0.0090(13) 0.0066(15) C17 0.0417(16) 0.0355(17) 0.0390(15) 0.0008(14) 0.0082(12) -0.0021(14) O4 0.0339(11) 0.0375(12) 0.0494(12) 0.0113(11) 0.0048(9) 0.0022(11) _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 N2 C8 1.360(4) . ? N2 C3 1.368(3) . ? N2 H2 1.00(4) . ? N5 N4 1.274(3) . ? N5 C11 1.419(3) . ? N4 C2 1.381(3) . ? C1 C16 1.363(4) . ? C1 C2 1.399(4) . ? C1 H1 1.04(3) . ? C2 C3 1.425(4) . ? C3 N1 1.325(4) . ? N3 C8 1.334(4) . ? N3 H3B 1.04(4) . ? N3 H3B 0.86(4) . ? N1 H1B 1.02(4) . ? N1 H1A 1.01(4) . ? C6 C10 1.379(4) . ? C6 C15 1.381(5) . ? C6 H8 0.96(4) . ? C7 C11 1.380(4) . ? C7 C18 1.384(4) . ? C7 H2 1.03(4) . ? C8 C16 1.411(4) . ? C10 C11 1.393(4) . ? C10 H6 0.93(4) . ? C15 C18 1.389(5) . ? C15 H15 0.99(3) . ? C16 H13 0.99(4) . ? C18 H10 0.98(4) . ? O1 C12 1.262(3) . ? O3 C5 1.365(3) . ? O3 H3 0.8200 . ? O2 C12 1.263(3) . ? C4 C9 1.402(4) . ? C4 C5 1.403(4) . ? C4 C12 1.496(4) . ? C5 C13 1.387(4) . ? C9 C17 1.378(4) . ? C9 H5A 1.00(3) . ? C13 C14 1.378(5) . ? C13 H7A 0.98(3) . ? C14 C17 1.395(4) . ? C14 H11A 0.99(3) . ? C17 H4A 0.99(4) . ? O4 H4B 0.96(4) . ? O4 H4A 0.87(6) . ? 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 C8 N2 C3 123.4(2) . . ? C8 N2 H2 122(2) . . ? C3 N2 H2 114(2) . . ? N4 N5 C11 115.2(2) . . ? N5 N4 C2 116.8(2) . . ? C16 C1 C2 122.7(3) . . ? C16 C1 H1 121.5(17) . . ? C2 C1 H1 115.6(17) . . ? N4 C2 C1 116.2(2) . . ? N4 C2 C3 125.8(2) . . ? C1 C2 C3 118.0(2) . . ? N1 C3 N2 118.3(3) . . ? N1 C3 C2 123.6(2) . . ? N2 C3 C2 118.1(2) . . ? C8 N3 H3B 121.9(18) . . ? C8 N3 H3B 119(3) . . ? H3B N3 H3B 119(3) . . ? C3 N1 H1B 123(2) . . ? C3 N1 H1A 116(3) . . ? H1B N1 H1A 121(3) . . ? C10 C6 C15 121.2(3) . . ? C10 C6 H8 123(2) . . ? C15 C6 H8 116(2) . . ? C11 C7 C18 120.6(3) . . ? C11 C7 H2 121.2(18) . . ? C18 C7 H2 118.2(18) . . ? N3 C8 N2 117.7(3) . . ? N3 C8 C16 123.0(3) . . ? N2 C8 C16 119.3(2) . . ? C6 C10 C11 119.3(3) . . ? C6 C10 H6 122(2) . . ? C11 C10 H6 118(2) . . ? C7 C11 C10 119.7(3) . . ? C7 C11 N5 114.8(3) . . ? C10 C11 N5 125.5(3) . . ? C6 C15 C18 119.3(3) . . ? C6 C15 H15 121(2) . . ? C18 C15 H15 119(2) . . ? C1 C16 C8 118.5(3) . . ? C1 C16 H13 123(2) . . ? C8 C16 H13 118(2) . . ? C7 C18 C15 119.7(3) . . ? C7 C18 H10 120(2) . . ? C15 C18 H10 120(2) . . ? C5 O3 H3 109.5 . . ? C9 C4 C5 117.6(3) . . ? C9 C4 C12 121.7(2) . . ? C5 C4 C12 120.7(2) . . ? O3 C5 C13 118.0(2) . . ? O3 C5 C4 121.5(3) . . ? C13 C5 C4 120.5(3) . . ? C17 C9 C4 121.8(3) . . ? C17 C9 H5A 120(2) . . ? C4 C9 H5A 118(2) . . ? O1 C12 O2 123.1(3) . . ? O1 C12 C4 119.5(2) . . ? O2 C12 C4 117.4(2) . . ? C14 C13 C5 120.7(3) . . ? C14 C13 H7A 118(2) . . ? C5 C13 H7A 121(2) . . ? C13 C14 C17 119.8(3) . . ? C13 C14 H11A 120.7(18) . . ? C17 C14 H11A 119.3(18) . . ? C9 C17 C14 119.5(3) . . ? C9 C17 H4A 115(2) . . ? C14 C17 H4A 125(2) . . ? H4B O4 H4A 109(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3B O2 1.04(4) 1.74(4) 2.778(3) 179(3) . N1 H1B O4 1.02(4) 1.85(4) 2.861(3) 168(3) . N2 H2 O1 1.00(4) 1.75(4) 2.747(3) 174(3) . N3 H3B O3 0.86(4) 2.07(4) 2.933(3) 173(3) 2_767 N1 H1A N5 1.01(4) 1.89(4) 2.645(3) 129(4) . O3 H3 O2 0.82 1.79 2.514(3) 147.0 . O4 H4B O1 0.96(4) 1.70(4) 2.631(3) 163(5) . O4 H4A O4 0.87(6) 2.01(6) 2.874(2) 171(5) 4_647 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 70.94 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.144 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 928352'