# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_5e _database_code_depnum_ccdc_archive 'CCDC 896683' #TrackingRef '13308_web_deposit_cif_file_0_RoyMcBurney_1345113143.5e.cif' _chemical_formula_sum 'C17 H17 N O4' _chemical_formula_moiety 'C17 H17 N O4' _chemical_formula_weight 299.33 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.892(3) _cell_length_b 7.5168(13) _cell_length_c 17.092(4) _cell_angle_alpha 90.0000 _cell_angle_beta 95.099(8) _cell_angle_gamma 90.0000 _cell_volume 1521.8(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5752 _cell_measurement_theta_min 4.75 _cell_measurement_theta_max 66.81 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632.00 _exptl_absorpt_coefficient_mu 0.772 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.9138 _exptl_absorpt_correction_T_max 0.9774 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 16358 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_theta_max 67.54 _diffrn_reflns_theta_full 67.55 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measured_fraction_theta_full 0.963 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2628 _reflns_number_gt 2293 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1086 _refine_ls_wR_factor_ref 0.3165 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2628 _refine_ls_number_parameters 199 _refine_ls_goodness_of_fit_ref 1.465 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1051P)^2^+2.9953P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.004 _refine_diff_density_max 0.320 _refine_diff_density_min -0.330 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O4 O 0.9085(4) 0.0668(6) 0.0504(3) 0.0486(11) Uani 1.0 4 d . . . O9 O 0.8914(3) 0.1688(5) 0.4931(2) 0.0413(10) Uani 1.0 4 d . . . O10 O 1.0578(4) 0.3173(6) 0.5183(3) 0.0464(11) Uani 1.0 4 d . . . O11 O 0.9254(3) 0.2969(5) 0.6041(2) 0.0422(10) Uani 1.0 4 d . . . N8 N 0.9193(4) 0.1543(6) 0.4135(3) 0.0389(12) Uani 1.0 4 d . . . C1 C 0.8645(5) 0.0425(7) 0.2889(3) 0.0339(12) Uani 1.0 4 d . . . C2 C 0.7826(5) -0.0265(7) 0.2344(4) 0.0361(13) Uani 1.0 4 d . . . C3 C 0.7942(5) -0.0231(7) 0.1548(4) 0.0362(13) Uani 1.0 4 d . . . C4 C 0.8896(5) 0.0510(7) 0.1273(3) 0.0382(13) Uani 1.0 4 d . . . C5 C 0.9743(5) 0.1179(8) 0.1813(4) 0.0413(14) Uani 1.0 4 d . . . C6 C 0.9622(5) 0.1116(7) 0.2601(4) 0.0387(13) Uani 1.0 4 d . . . C7 C 0.8471(5) 0.0544(7) 0.3738(3) 0.0343(12) Uani 1.0 4 d . . . C10 C 0.9693(5) 0.2681(7) 0.5367(3) 0.0345(12) Uani 1.0 4 d . . . C12 C 0.9939(5) 0.4083(8) 0.6592(4) 0.0441(14) Uani 1.0 4 d . . . C13 C 0.9296(5) 0.4369(7) 0.7296(3) 0.0340(12) Uani 1.0 4 d . . . C14 C 0.9685(6) 0.3650(8) 0.8013(4) 0.0444(15) Uani 1.0 4 d . . . C15 C 0.9090(7) 0.3908(10) 0.8664(4) 0.0597(18) Uani 1.0 4 d . . . C16 C 0.8095(7) 0.4865(11) 0.8592(5) 0.066(2) Uani 1.0 4 d . . . C17 C 0.7710(6) 0.5571(9) 0.7881(5) 0.0586(18) Uani 1.0 4 d . . . C18 C 0.8305(5) 0.5324(8) 0.7238(4) 0.0443(14) Uani 1.0 4 d . . . C19 C 0.8273(5) -0.0096(10) -0.0064(4) 0.0533(17) Uani 1.0 4 d . . . C20 C 0.7503(6) -0.0338(9) 0.4070(4) 0.0488(15) Uani 1.0 4 d . . . H2 H 0.7165 -0.0777 0.2524 0.0434 Uiso 1.0 4 calc R . . H3 H 0.7366 -0.0716 0.1189 0.0435 Uiso 1.0 4 calc R . . H5 H 1.0406 0.1679 0.1632 0.0495 Uiso 1.0 4 calc R . . H6 H 1.0214 0.1549 0.2960 0.0465 Uiso 1.0 4 calc R . . H12A H 1.0094 0.5238 0.6345 0.0529 Uiso 1.0 4 calc R . . H12B H 1.0668 0.3492 0.6749 0.0529 Uiso 1.0 4 calc R . . H14 H 1.0363 0.2976 0.8060 0.0533 Uiso 1.0 4 calc R . . H15 H 0.9365 0.3428 0.9159 0.0717 Uiso 1.0 4 calc R . . H16 H 0.7678 0.5032 0.9036 0.0792 Uiso 1.0 4 calc R . . H17 H 0.7028 0.6236 0.7832 0.0703 Uiso 1.0 4 calc R . . H18 H 0.8030 0.5818 0.6747 0.0532 Uiso 1.0 4 calc R . . H19A H 0.8475 0.0190 -0.0593 0.0639 Uiso 1.0 4 calc R . . H19B H 0.7524 0.0388 0.0007 0.0639 Uiso 1.0 4 calc R . . H19C H 0.8263 -0.1391 0.0004 0.0639 Uiso 1.0 4 calc R . . H20A H 0.7014 0.0565 0.4276 0.0585 Uiso 1.0 4 calc R . . H20B H 0.7784 -0.1140 0.4495 0.0585 Uiso 1.0 4 calc R . . H20C H 0.7072 -0.1022 0.3657 0.0585 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O4 0.043(3) 0.065(3) 0.038(3) -0.007(2) 0.0067(18) -0.0094(19) O9 0.039(2) 0.049(3) 0.037(2) -0.0111(18) 0.0069(17) -0.0099(17) O10 0.036(3) 0.057(3) 0.047(3) -0.0101(19) 0.0080(18) -0.0040(19) O11 0.042(3) 0.048(3) 0.037(2) -0.0139(18) 0.0072(17) -0.0102(17) N8 0.045(3) 0.041(3) 0.031(3) 0.001(2) 0.007(2) -0.002(2) C1 0.033(3) 0.027(3) 0.041(3) 0.007(3) -0.001(3) -0.001(3) C2 0.030(3) 0.033(3) 0.045(4) 0.000(3) 0.003(3) 0.002(3) C3 0.034(3) 0.032(3) 0.041(3) 0.002(3) -0.004(3) -0.006(3) C4 0.041(3) 0.036(3) 0.038(3) 0.005(3) 0.004(3) -0.005(3) C5 0.034(3) 0.043(4) 0.046(4) -0.007(3) 0.005(3) -0.009(3) C6 0.034(3) 0.037(3) 0.044(4) 0.001(3) -0.000(3) -0.008(3) C7 0.033(3) 0.026(3) 0.042(3) -0.000(3) -0.003(3) -0.003(3) C10 0.037(3) 0.033(3) 0.034(3) 0.002(3) 0.005(3) -0.002(3) C12 0.045(4) 0.044(4) 0.044(4) -0.009(3) 0.006(3) -0.011(3) C13 0.034(3) 0.030(3) 0.037(3) -0.004(3) -0.003(3) -0.003(3) C14 0.048(4) 0.038(4) 0.047(4) 0.004(3) 0.003(3) 0.001(3) C15 0.079(5) 0.066(5) 0.034(4) -0.009(4) 0.001(4) 0.007(3) C16 0.075(5) 0.074(5) 0.053(5) -0.007(4) 0.027(4) -0.014(4) C17 0.049(4) 0.047(4) 0.081(6) 0.003(3) 0.016(4) -0.017(4) C18 0.047(4) 0.036(3) 0.047(4) 0.003(3) -0.006(3) -0.000(3) C19 0.045(4) 0.073(5) 0.042(4) -0.001(3) 0.001(3) -0.013(3) C20 0.050(4) 0.055(4) 0.042(4) -0.014(3) 0.004(3) -0.003(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O4 C4 1.357(7) yes . . O4 C19 1.428(7) yes . . O9 N8 1.432(6) yes . . O9 C10 1.359(7) yes . . O10 C10 1.184(7) yes . . O11 C10 1.325(7) yes . . O11 C12 1.454(7) yes . . N8 C7 1.288(7) yes . . C1 C2 1.388(7) yes . . C1 C6 1.402(8) yes . . C1 C7 1.485(8) yes . . C2 C3 1.381(8) yes . . C3 C4 1.383(8) yes . . C4 C5 1.398(8) yes . . C5 C6 1.367(8) yes . . C7 C20 1.484(9) yes . . C12 C13 1.497(8) yes . . C13 C14 1.381(8) yes . . C13 C18 1.376(8) yes . . C14 C15 1.384(10) yes . . C15 C16 1.381(11) yes . . C16 C17 1.368(11) yes . . C17 C18 1.371(10) yes . . C2 H2 0.950 no . . C3 H3 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C12 H12A 0.990 no . . C12 H12B 0.990 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19A 0.980 no . . C19 H19B 0.980 no . . C19 H19C 0.980 no . . C20 H20A 0.980 no . . C20 H20B 0.980 no . . C20 H20C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C4 O4 C19 117.6(5) yes . . . N8 O9 C10 111.0(4) yes . . . C10 O11 C12 114.6(5) yes . . . O9 N8 C7 110.2(5) yes . . . C2 C1 C6 117.1(5) yes . . . C2 C1 C7 121.9(5) yes . . . C6 C1 C7 120.9(5) yes . . . C1 C2 C3 122.0(5) yes . . . C2 C3 C4 119.9(5) yes . . . O4 C4 C3 125.1(5) yes . . . O4 C4 C5 115.9(5) yes . . . C3 C4 C5 119.0(5) yes . . . C4 C5 C6 120.4(6) yes . . . C1 C6 C5 121.5(5) yes . . . N8 C7 C1 114.0(5) yes . . . N8 C7 C20 124.2(5) yes . . . C1 C7 C20 121.7(5) yes . . . O9 C10 O10 127.2(5) yes . . . O9 C10 O11 105.3(5) yes . . . O10 C10 O11 127.4(5) yes . . . O11 C12 C13 107.9(5) yes . . . C12 C13 C14 120.2(5) yes . . . C12 C13 C18 120.8(5) yes . . . C14 C13 C18 119.0(6) yes . . . C13 C14 C15 120.3(6) yes . . . C14 C15 C16 119.8(6) yes . . . C15 C16 C17 119.8(7) yes . . . C16 C17 C18 120.3(7) yes . . . C13 C18 C17 120.9(6) yes . . . C1 C2 H2 118.999 no . . . C3 C2 H2 119.015 no . . . C2 C3 H3 120.032 no . . . C4 C3 H3 120.030 no . . . C4 C5 H5 119.817 no . . . C6 C5 H5 119.828 no . . . C1 C6 H6 119.252 no . . . C5 C6 H6 119.245 no . . . O11 C12 H12A 110.132 no . . . O11 C12 H12B 110.133 no . . . C13 C12 H12A 110.132 no . . . C13 C12 H12B 110.131 no . . . H12A C12 H12B 108.448 no . . . C13 C14 H14 119.856 no . . . C15 C14 H14 119.855 no . . . C14 C15 H15 120.101 no . . . C16 C15 H15 120.105 no . . . C15 C16 H16 120.104 no . . . C17 C16 H16 120.098 no . . . C16 C17 H17 119.870 no . . . C18 C17 H17 119.858 no . . . C13 C18 H18 119.553 no . . . C17 C18 H18 119.559 no . . . O4 C19 H19A 109.472 no . . . O4 C19 H19B 109.478 no . . . O4 C19 H19C 109.472 no . . . H19A C19 H19B 109.468 no . . . H19A C19 H19C 109.466 no . . . H19B C19 H19C 109.472 no . . . C7 C20 H20A 109.476 no . . . C7 C20 H20B 109.478 no . . . C7 C20 H20C 109.479 no . . . H20A C20 H20B 109.462 no . . . H20A C20 H20C 109.462 no . . . H20B C20 H20C 109.471 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C19 O4 C4 C3 -4.4(8) no . . . . C19 O4 C4 C5 176.2(5) no . . . . N8 O9 C10 O10 -10.5(7) no . . . . N8 O9 C10 O11 169.8(4) no . . . . C10 O9 N8 C7 177.6(4) no . . . . C10 O11 C12 C13 176.6(4) no . . . . C12 O11 C10 O9 -177.6(4) no . . . . C12 O11 C10 O10 2.7(8) no . . . . O9 N8 C7 C1 175.7(4) no . . . . O9 N8 C7 C20 -0.8(7) no . . . . C2 C1 C6 C5 2.8(8) no . . . . C6 C1 C2 C3 -2.0(8) no . . . . C2 C1 C7 N8 -166.1(5) no . . . . C2 C1 C7 C20 10.5(7) no . . . . C7 C1 C2 C3 174.0(4) no . . . . C6 C1 C7 N8 9.9(7) no . . . . C6 C1 C7 C20 -173.6(5) no . . . . C7 C1 C6 C5 -173.3(4) no . . . . C1 C2 C3 C4 -0.1(8) no . . . . C2 C3 C4 O4 -177.8(5) no . . . . C2 C3 C4 C5 1.5(8) no . . . . O4 C4 C5 C6 178.7(5) no . . . . C3 C4 C5 C6 -0.7(8) no . . . . C4 C5 C6 C1 -1.5(8) no . . . . O11 C12 C13 C14 112.8(5) no . . . . O11 C12 C13 C18 -66.2(6) no . . . . C12 C13 C14 C15 -179.8(5) no . . . . C12 C13 C18 C17 179.3(5) no . . . . C14 C13 C18 C17 0.3(8) no . . . . C18 C13 C14 C15 -0.8(8) no . . . . C13 C14 C15 C16 1.0(10) no . . . . C14 C15 C16 C17 -0.8(11) no . . . . C15 C16 C17 C18 0.4(11) no . . . . C16 C17 C18 C13 -0.1(10) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O4 C6 3.599(7) no . . O9 C12 3.489(7) no . . O9 C20 2.620(7) no . . O10 N8 2.627(6) no . . O10 C12 2.678(8) no . . O11 N8 3.424(6) no . . O11 C14 3.403(7) no . . O11 C18 3.000(7) no . . N8 C6 2.735(7) no . . C1 C4 2.806(8) no . . C2 C5 2.751(8) no . . C2 C20 3.008(9) no . . C3 C6 2.760(8) no . . C3 C19 2.819(9) no . . C7 C10 3.424(8) no . . C13 C16 2.766(10) no . . C14 C17 2.748(9) no . . C15 C18 2.745(9) no . . O4 O4 3.063(6) no . 3_755 O4 C19 3.323(8) no . 3_755 O9 N8 3.589(6) no . 3_756 O9 C19 3.573(8) no . 2_655 O10 O10 3.110(6) no . 3_766 O10 O11 3.592(6) no . 3_766 O10 C7 3.481(7) no . 3_756 O10 C10 3.263(7) no . 3_766 O10 C19 3.575(8) no . 4_555 O10 C20 3.295(8) no . 3_756 O11 O10 3.592(6) no . 3_766 O11 C17 3.586(8) no . 2_646 N8 O9 3.589(6) no . 3_756 N8 C10 3.515(7) no . 3_756 C4 C20 3.560(9) no . 2_655 C7 O10 3.481(7) no . 3_756 C7 C10 3.520(7) no . 3_756 C10 O10 3.263(7) no . 3_766 C10 N8 3.515(7) no . 3_756 C10 C7 3.520(7) no . 3_756 C17 O11 3.586(8) no . 2_656 C19 O4 3.323(8) no . 3_755 C19 O9 3.573(8) no . 2_645 C19 O10 3.575(8) no . 4_454 C20 O10 3.295(8) no . 3_756 C20 C4 3.560(9) no . 2_645 O4 H3 2.6555 no . . O4 H5 2.4945 no . . O9 H20A 2.5734 no . . O9 H20B 2.5891 no . . O9 H20C 3.5838 no . . O10 H12A 2.6245 no . . O10 H12B 2.6794 no . . O11 H14 3.5831 no . . O11 H18 2.9106 no . . N8 H6 2.4376 no . . N8 H20A 2.7247 no . . N8 H20B 2.7267 no . . N8 H20C 3.2220 no . . C1 H3 3.2729 no . . C1 H5 3.2705 no . . C1 H20A 3.1948 no . . C1 H20B 3.2343 no . . C1 H20C 2.6154 no . . C2 H6 3.2409 no . . C2 H20A 3.5766 no . . C2 H20C 2.5535 no . . C3 H5 3.2554 no . . C3 H19B 2.6763 no . . C3 H19C 2.8369 no . . C4 H2 3.2452 no . . C4 H6 3.2527 no . . C4 H19A 3.1932 no . . C4 H19B 2.5928 no . . C4 H19C 2.6499 no . . C5 H3 3.2586 no . . C6 H2 3.2420 no . . C7 H2 2.6692 no . . C7 H6 2.6688 no . . C10 H12A 2.5649 no . . C10 H12B 2.6098 no . . C12 H14 2.6490 no . . C12 H18 2.6518 no . . C13 H15 3.2549 no . . C13 H17 3.2435 no . . C14 H12A 3.1679 no . . C14 H12B 2.5496 no . . C14 H16 3.2506 no . . C14 H18 3.2336 no . . C15 H17 3.2366 no . . C16 H14 3.2488 no . . C16 H18 3.2288 no . . C17 H15 3.2361 no . . C18 H12A 2.7271 no . . C18 H12B 3.3027 no . . C18 H14 3.2346 no . . C18 H16 3.2324 no . . C19 H3 2.5246 no . . C20 H2 2.6564 no . . H2 H3 2.3171 no . . H2 H20A 3.1796 no . . H2 H20B 3.3939 no . . H2 H20C 1.9576 no . . H3 H19A 3.4914 no . . H3 H19B 2.2064 no . . H3 H19C 2.4246 no . . H5 H6 2.3035 no . . H12A H14 3.3789 no . . H12A H18 2.6435 no . . H12B H14 2.3342 no . . H12B H18 3.5915 no . . H14 H15 2.3330 no . . H15 H16 2.3339 no . . H16 H17 2.3172 no . . H17 H18 2.3123 no . . O4 H15 3.1378 no . 1_554 O4 H19A 2.9626 no . 3_755 O4 H19C 3.3883 no . 3_755 O4 H20B 3.2709 no . 2_655 O4 H20C 3.2385 no . 2_655 O9 H3 3.0444 no . 2_655 O9 H12A 3.4559 no . 3_766 O9 H16 2.9750 no . 2_646 O9 H19B 3.2715 no . 2_655 O9 H19C 2.9753 no . 2_655 O10 H3 3.2370 no . 4_555 O10 H12A 2.9190 no . 3_766 O10 H19B 2.5958 no . 4_555 O10 H20B 2.4980 no . 3_756 O11 H16 3.1804 no . 2_646 O11 H17 2.8730 no . 2_646 O11 H19B 3.2113 no . 2_655 O11 H19C 3.3804 no . 2_655 N8 H3 2.7943 no . 2_655 N8 H12A 2.7154 no . 3_766 C1 H2 3.0751 no . 2_655 C1 H3 3.5607 no . 2_655 C1 H12B 3.1034 no . 3_756 C1 H14 3.3022 no . 3_756 C2 H2 3.3812 no . 2_655 C2 H12A 3.5328 no . 4_454 C2 H12B 3.3168 no . 3_756 C2 H12B 2.9884 no . 4_454 C2 H14 3.0878 no . 3_756 C3 H12A 3.3730 no . 4_454 C3 H12B 3.0499 no . 4_454 C3 H14 2.9211 no . 3_756 C3 H20A 3.4622 no . 2_645 C3 H20C 3.1826 no . 2_655 C4 H14 2.9605 no . 3_756 C4 H19A 3.4706 no . 3_755 C4 H20B 3.4038 no . 2_655 C4 H20C 2.8560 no . 2_655 C5 H2 3.4823 no . 2_655 C5 H14 3.1336 no . 3_756 C5 H17 3.5871 no . 4_554 C5 H19A 3.2681 no . 3_755 C5 H20C 3.0695 no . 2_655 C6 H2 3.1528 no . 2_655 C6 H12A 3.2811 no . 3_766 C6 H14 3.2767 no . 3_756 C6 H17 3.3563 no . 4_554 C6 H20C 3.5407 no . 2_655 C7 H2 3.5470 no . 2_655 C7 H3 2.9887 no . 2_655 C7 H12B 3.3313 no . 3_756 C10 H12A 3.3475 no . 3_766 C10 H19B 3.3471 no . 2_655 C10 H19C 3.5849 no . 2_655 C10 H20B 3.2046 no . 3_756 C12 H2 3.2283 no . 4_555 C12 H3 3.2668 no . 4_555 C12 H6 3.3801 no . 3_766 C12 H17 3.3808 no . 2_646 C13 H2 3.5600 no . 4_555 C13 H5 3.4914 no . 3_766 C13 H6 3.1606 no . 3_766 C13 H17 2.8313 no . 2_646 C14 H2 3.5204 no . 4_555 C14 H5 3.5661 no . 3_766 C14 H17 3.0011 no . 2_646 C14 H20A 3.4082 no . 4_555 C14 H20C 3.4485 no . 4_555 C15 H5 3.4164 no . 3_766 C15 H17 3.4256 no . 2_646 C15 H18 3.4536 no . 2_646 C15 H19A 3.1819 no . 1_556 C15 H20A 3.5628 no . 4_555 C16 H5 3.1930 no . 3_766 C16 H18 3.3526 no . 2_646 C16 H20B 3.5997 no . 2_656 C17 H5 3.1065 no . 3_766 C17 H6 3.3827 no . 4_455 C17 H17 3.5025 no . 2_646 C18 H5 3.2595 no . 3_766 C18 H6 2.9745 no . 3_766 C18 H17 3.0994 no . 2_646 C18 H19A 3.3679 no . 2_655 C19 H5 3.4371 no . 3_755 C19 H15 3.2832 no . 1_554 C19 H18 3.2177 no . 2_645 C19 H20A 3.5566 no . 2_645 C19 H20B 3.4037 no . 2_655 C20 H3 3.5079 no . 2_655 C20 H12B 3.5845 no . 3_756 C20 H14 3.4390 no . 4_454 C20 H16 3.2761 no . 2_646 C20 H19B 3.5802 no . 2_645 C20 H19C 3.5214 no . 2_655 H2 C1 3.0751 no . 2_645 H2 C2 3.3812 no . 2_645 H2 C5 3.4823 no . 2_645 H2 C6 3.1528 no . 2_645 H2 C7 3.5470 no . 2_645 H2 C12 3.2283 no . 4_454 H2 C13 3.5600 no . 4_454 H2 C14 3.5204 no . 4_454 H2 H6 3.5092 no . 2_645 H2 H12A 3.0674 no . 4_454 H2 H12B 3.4320 no . 3_756 H2 H12B 2.7307 no . 4_454 H2 H14 3.5907 no . 3_756 H2 H14 3.1958 no . 4_454 H3 O9 3.0444 no . 2_645 H3 O10 3.2370 no . 4_454 H3 N8 2.7943 no . 2_645 H3 C1 3.5607 no . 2_645 H3 C7 2.9887 no . 2_645 H3 C12 3.2668 no . 4_454 H3 C20 3.5079 no . 2_645 H3 H12A 2.7624 no . 4_454 H3 H12B 2.8521 no . 4_454 H3 H14 3.3482 no . 3_756 H3 H20A 3.0160 no . 2_645 H3 H20C 3.5960 no . 2_655 H5 C13 3.4914 no . 3_766 H5 C14 3.5661 no . 3_766 H5 C15 3.4164 no . 3_766 H5 C16 3.1930 no . 3_766 H5 C17 3.1065 no . 3_766 H5 C18 3.2595 no . 3_766 H5 C19 3.4371 no . 3_755 H5 H17 3.4795 no . 3_766 H5 H17 3.4672 no . 4_554 H5 H19A 2.7047 no . 3_755 H5 H19C 3.3400 no . 3_755 H5 H20C 3.4138 no . 2_655 H6 C12 3.3801 no . 3_766 H6 C13 3.1606 no . 3_766 H6 C17 3.3827 no . 4_554 H6 C18 2.9745 no . 3_766 H6 H2 3.5092 no . 2_655 H6 H12A 2.7302 no . 3_766 H6 H16 3.5248 no . 4_554 H6 H17 3.0280 no . 4_554 H6 H18 2.8886 no . 3_766 H12A O9 3.4559 no . 3_766 H12A O10 2.9190 no . 3_766 H12A N8 2.7154 no . 3_766 H12A C2 3.5328 no . 4_555 H12A C3 3.3730 no . 4_555 H12A C6 3.2811 no . 3_766 H12A C10 3.3475 no . 3_766 H12A H2 3.0674 no . 4_555 H12A H3 2.7624 no . 4_555 H12A H6 2.7302 no . 3_766 H12B C1 3.1034 no . 3_756 H12B C2 3.3168 no . 3_756 H12B C2 2.9884 no . 4_555 H12B C3 3.0499 no . 4_555 H12B C7 3.3313 no . 3_756 H12B C20 3.5845 no . 3_756 H12B H2 3.4320 no . 3_756 H12B H2 2.7307 no . 4_555 H12B H3 2.8521 no . 4_555 H12B H20B 3.4247 no . 3_756 H12B H20C 3.3889 no . 3_756 H14 C1 3.3022 no . 3_756 H14 C2 3.0878 no . 3_756 H14 C3 2.9211 no . 3_756 H14 C4 2.9605 no . 3_756 H14 C5 3.1336 no . 3_756 H14 C6 3.2767 no . 3_756 H14 C20 3.4390 no . 4_555 H14 H2 3.5907 no . 3_756 H14 H2 3.1958 no . 4_555 H14 H3 3.3482 no . 3_756 H14 H17 3.3690 no . 2_646 H14 H20A 2.9415 no . 4_555 H14 H20C 3.1694 no . 4_555 H15 O4 3.1378 no . 1_556 H15 C19 3.2832 no . 1_556 H15 H19A 2.7034 no . 1_556 H15 H19B 3.5619 no . 1_556 H15 H19C 3.4106 no . 3_756 H15 H20A 3.2277 no . 4_555 H16 O9 2.9750 no . 2_656 H16 O11 3.1804 no . 2_656 H16 C20 3.2761 no . 2_656 H16 H6 3.5248 no . 4_455 H16 H18 3.5117 no . 2_646 H16 H19C 3.2011 no . 1_566 H16 H20A 2.9033 no . 2_656 H16 H20B 2.7623 no . 2_656 H17 O11 2.8730 no . 2_656 H17 C5 3.5871 no . 4_455 H17 C6 3.3563 no . 4_455 H17 C12 3.3808 no . 2_656 H17 C13 2.8313 no . 2_656 H17 C14 3.0011 no . 2_656 H17 C15 3.4256 no . 2_656 H17 C17 3.5025 no . 2_656 H17 C18 3.0994 no . 2_656 H17 H5 3.4795 no . 3_766 H17 H5 3.4672 no . 4_455 H17 H6 3.0280 no . 4_455 H17 H14 3.3690 no . 2_656 H17 H18 3.5209 no . 2_656 H18 C15 3.4536 no . 2_656 H18 C16 3.3526 no . 2_656 H18 C19 3.2177 no . 2_655 H18 H6 2.8886 no . 3_766 H18 H16 3.5117 no . 2_656 H18 H17 3.5209 no . 2_646 H18 H19A 2.5857 no . 2_655 H18 H19B 3.0291 no . 2_655 H19A O4 2.9626 no . 3_755 H19A C4 3.4706 no . 3_755 H19A C5 3.2681 no . 3_755 H19A C15 3.1819 no . 1_554 H19A C18 3.3679 no . 2_645 H19A H5 2.7047 no . 3_755 H19A H15 2.7034 no . 1_554 H19A H18 2.5857 no . 2_645 H19B O9 3.2715 no . 2_645 H19B O10 2.5958 no . 4_454 H19B O11 3.2113 no . 2_645 H19B C10 3.3471 no . 2_645 H19B C20 3.5802 no . 2_655 H19B H15 3.5619 no . 1_554 H19B H18 3.0291 no . 2_645 H19B H20B 2.7789 no . 2_655 H19B H20C 3.5396 no . 2_655 H19C O4 3.3883 no . 3_755 H19C O9 2.9753 no . 2_645 H19C O11 3.3804 no . 2_645 H19C C10 3.5849 no . 2_645 H19C C20 3.5214 no . 2_645 H19C H5 3.3400 no . 3_755 H19C H15 3.4106 no . 3_756 H19C H16 3.2011 no . 1_544 H19C H20A 2.6330 no . 2_645 H20A C3 3.4622 no . 2_655 H20A C14 3.4082 no . 4_454 H20A C15 3.5628 no . 4_454 H20A C19 3.5566 no . 2_655 H20A H3 3.0160 no . 2_655 H20A H14 2.9415 no . 4_454 H20A H15 3.2277 no . 4_454 H20A H16 2.9033 no . 2_646 H20A H19C 2.6330 no . 2_655 H20B O4 3.2709 no . 2_645 H20B O10 2.4980 no . 3_756 H20B C4 3.4038 no . 2_645 H20B C10 3.2046 no . 3_756 H20B C16 3.5997 no . 2_646 H20B C19 3.4037 no . 2_645 H20B H12B 3.4247 no . 3_756 H20B H16 2.7623 no . 2_646 H20B H19B 2.7789 no . 2_645 H20C O4 3.2385 no . 2_645 H20C C3 3.1826 no . 2_645 H20C C4 2.8560 no . 2_645 H20C C5 3.0695 no . 2_645 H20C C6 3.5407 no . 2_645 H20C C14 3.4485 no . 4_454 H20C H3 3.5960 no . 2_645 H20C H5 3.4138 no . 2_645 H20C H12B 3.3889 no . 3_756 H20C H14 3.1694 no . 4_454 H20C H19B 3.5396 no . 2_645 data_9a _database_code_depnum_ccdc_archive 'CCDC 896684' #TrackingRef '13309_web_deposit_cif_file_1_RoyMcBurney_1345113143.9a.cif' _chemical_formula_sum 'C11 H9 N O3' _chemical_formula_moiety 'C11 H9 N O3' _chemical_formula_weight 203.20 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2+Z 3 +X,1/2-Y,+Z 4 1/2-X,-Y,1/2+Z 5 -X,-Y,-Z 6 1/2+X,1/2-Y,1/2-Z 7 -X,1/2+Y,-Z 8 1/2+X,+Y,1/2-Z #------------------------------------------------------------------------------ _cell_length_a 19.168(13) _cell_length_b 6.189(5) _cell_length_c 8.461(5) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1003.7(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2859 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424.00 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.990 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 5804 _diffrn_reflns_av_R_equivalents 0.1655 _diffrn_reflns_theta_max 25.37 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1006 _reflns_number_gt 814 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.2968 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1006 _refine_ls_number_parameters 92 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.132 _refine_diff_density_max 0.700 _refine_diff_density_min -0.410 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O9 O 0.59412(14) 0.7500 -0.0557(3) 0.0502(10) Uani 1.0 4 d . . . O10 O 0.47705(12) 0.7500 0.0015(3) 0.0495(11) Uani 1.0 4 d . . . O11 O 0.52096(12) 0.7500 -0.2473(3) 0.0465(10) Uani 1.0 4 d . . . N8 N 0.60559(16) 0.7500 0.1130(4) 0.0461(11) Uani 1.0 4 d . . . C1 C 0.70018(19) 0.7500 0.2963(5) 0.0441(12) Uani 1.0 4 d . . . C2 C 0.6579(2) 0.7500 0.4311(5) 0.0506(12) Uani 1.0 4 d . . . C3 C 0.6880(2) 0.7500 0.5792(4) 0.0516(13) Uani 1.0 4 d . . . C4 C 0.7600(2) 0.7500 0.5963(5) 0.0517(12) Uani 1.0 4 d . . . C5 C 0.8029(2) 0.7500 0.4647(5) 0.0515(12) Uani 1.0 4 d . . . C6 C 0.77310(19) 0.7500 0.3141(5) 0.0462(12) Uani 1.0 4 d . . . C7 C 0.6708(2) 0.7500 0.1354(4) 0.0447(11) Uani 1.0 4 d . . . C10 C 0.52486(19) 0.7500 -0.0884(5) 0.0427(12) Uani 1.0 4 d . . . C12 C 0.4499(2) 0.7500 -0.3060(4) 0.0463(12) Uani 1.0 4 d . . . C13 C 0.45361(19) 0.7500 -0.4797(4) 0.0448(11) Uani 1.0 4 d . . . C14 C 0.45514(19) 0.7500 -0.6208(5) 0.0479(12) Uani 1.0 4 d . . . H2 H 0.6085 0.7500 0.4207 0.0607 Uiso 1.0 4 calc R . . H3 H 0.6591 0.7500 0.6705 0.0619 Uiso 1.0 4 calc R . . H4 H 0.7800 0.7500 0.6990 0.0621 Uiso 1.0 4 calc R . . H5 H 0.8521 0.7500 0.4767 0.0618 Uiso 1.0 4 calc R . . H6 H 0.8022 0.7500 0.2233 0.0554 Uiso 1.0 4 calc R . . H7 H 0.7014 0.7500 0.0470 0.0536 Uiso 1.0 4 calc R . . H12A H 0.4247 0.8798 -0.2682 0.0556 Uiso 0.5000 8 calc R . . H12B H 0.4247 0.6202 -0.2682 0.0556 Uiso 0.5000 8 calc R . . H14 H 0.4564 0.7500 -0.7330 0.0575 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O9 0.0462(18) 0.077(2) 0.0276(16) 0.0000 0.0017(11) 0.0000 O10 0.0391(18) 0.076(3) 0.0336(16) 0.0000 0.0008(11) 0.0000 O11 0.0418(19) 0.073(3) 0.0248(16) 0.0000 0.0028(10) 0.0000 N8 0.044(2) 0.069(3) 0.0258(18) 0.0000 -0.0015(12) 0.0000 C1 0.043(3) 0.053(3) 0.037(3) 0.0000 -0.0028(16) 0.0000 C2 0.040(3) 0.065(3) 0.047(3) 0.0000 0.0009(17) 0.0000 C3 0.051(3) 0.066(3) 0.038(3) 0.0000 0.0013(17) 0.0000 C4 0.052(3) 0.059(3) 0.044(3) 0.0000 -0.0109(18) 0.0000 C5 0.043(3) 0.055(3) 0.056(3) 0.0000 -0.0109(19) 0.0000 C6 0.039(3) 0.059(3) 0.040(3) 0.0000 0.0025(16) 0.0000 C7 0.043(3) 0.053(3) 0.038(3) 0.0000 0.0069(16) 0.0000 C10 0.041(3) 0.053(3) 0.034(3) 0.0000 0.0061(15) 0.0000 C12 0.042(3) 0.064(3) 0.033(3) 0.0000 -0.0023(16) 0.0000 C13 0.044(3) 0.055(3) 0.035(3) 0.0000 -0.0021(16) 0.0000 C14 0.045(3) 0.062(3) 0.037(3) 0.0000 -0.0032(17) 0.0000 #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'Superflip (Palatinus, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O9 N8 1.444(5) yes . . O9 C10 1.356(5) yes . . O10 C10 1.191(5) yes . . O11 C10 1.346(5) yes . . O11 C12 1.450(5) yes . . N8 C7 1.264(5) yes . . C1 C2 1.399(6) yes . . C1 C6 1.406(6) yes . . C1 C7 1.473(6) yes . . C2 C3 1.379(6) yes . . C3 C4 1.388(6) yes . . C4 C5 1.384(6) yes . . C5 C6 1.396(6) yes . . C12 C13 1.471(5) yes . . C13 C14 1.194(6) yes . . C2 H2 0.951 no . . C3 H3 0.951 no . . C4 H4 0.950 no . . C5 H5 0.949 no . . C6 H6 0.950 no . . C7 H7 0.951 no . . C12 H12A 0.990 no . . C12 H12A 0.990 no . 3_565 C12 H12B 0.990 no . . C12 H12B 0.990 no . 3_565 C14 H14 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 N8 O9 C10 110.5(3) yes . . . C10 O11 C12 113.2(3) yes . . . O9 N8 C7 107.4(3) yes . . . C2 C1 C6 119.2(4) yes . . . C2 C1 C7 122.1(4) yes . . . C6 C1 C7 118.6(4) yes . . . C1 C2 C3 119.9(4) yes . . . C2 C3 C4 120.7(4) yes . . . C3 C4 C5 120.5(4) yes . . . C4 C5 C6 119.4(4) yes . . . C1 C6 C5 120.3(4) yes . . . N8 C7 C1 121.1(4) yes . . . O9 C10 O10 128.5(4) yes . . . O9 C10 O11 105.0(3) yes . . . O10 C10 O11 126.5(4) yes . . . O11 C12 C13 107.3(3) yes . . . C12 C13 C14 178.6(4) yes . . . C1 C2 H2 120.075 no . . . C3 C2 H2 120.045 no . . . C2 C3 H3 119.616 no . . . C4 C3 H3 119.676 no . . . C3 C4 H4 119.791 no . . . C5 C4 H4 119.746 no . . . C4 C5 H5 120.298 no . . . C6 C5 H5 120.295 no . . . C1 C6 H6 119.873 no . . . C5 C6 H6 119.831 no . . . N8 C7 H7 119.495 no . . . C1 C7 H7 119.410 no . . . O11 C12 H12A 110.314 no . . . O11 C12 H12A 110.314 no . . 3_565 O11 C12 H12B 110.314 no . . . O11 C12 H12B 110.314 no . . 3_565 C13 C12 H12A 110.235 no . . . C13 C12 H12A 110.235 no . . 3_565 C13 C12 H12B 110.235 no . . . C13 C12 H12B 110.235 no . . 3_565 H12A C12 H12A 108.483 no . . 3_565 H12A C12 H12B 108.483 no . . . H12A C12 H12B 0.000 no . . 3_565 H12A C12 H12B 0.000 no 3_565 . . H12A C12 H12B 108.483 no 3_565 . 3_565 H12B C12 H12B 108.483 no . . 3_565 C13 C14 H14 179.985 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N8 O9 C10 O10 0.0 no . . . . N8 O9 C10 O11 180.0 no . . . . C10 O9 N8 C7 180.0 no . . . . C10 O11 C12 C13 180.0 no . . . . C12 O11 C10 O9 180.0 no . . . . C12 O11 C10 O10 0.0 no . . . . O9 N8 C7 C1 180.0 no . . . . C2 C1 C6 C5 0.0 no . . . . C6 C1 C2 C3 0.0 no . . . . C2 C1 C7 N8 0.0 no . . . . C7 C1 C2 C3 180.0 no . . . . C6 C1 C7 N8 180.0 no . . . . C7 C1 C6 C5 180.0 no . . . . C1 C2 C3 C4 0.0 no . . . . C2 C3 C4 C5 0.0 no . . . . C3 C4 C5 C6 0.0 no . . . . C4 C5 C6 C1 0.0 no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O9 C12 3.482(5) no . . O10 N8 2.638(5) no . . O10 C12 2.653(5) no . . O11 N8 3.453(5) no . . O11 C14 3.403(6) no . . N8 C2 2.872(6) no . . C1 C4 2.785(6) no . . C2 C5 2.794(6) no . . C3 C6 2.773(6) no . . C7 C10 3.378(6) no . . C10 C13 3.581(6) no . . O9 O10 3.413(3) no . 5_665 O9 O10 3.413(3) no . 5_675 O9 C3 3.575(5) no . 1_554 O10 O9 3.413(3) no . 5_665 O10 O9 3.413(3) no . 5_675 O10 O10 3.217(3) no . 5_665 O10 O10 3.217(3) no . 5_675 O10 C5 3.350(5) no . 6_465 O10 C10 3.181(3) no . 5_665 O10 C10 3.181(3) no . 5_675 O10 C14 3.223(6) no . 1_556 O11 C3 3.522(5) no . 1_554 O11 C14 3.322(3) no . 5_664 O11 C14 3.322(3) no . 5_674 C3 O9 3.575(5) no . 1_556 C3 O11 3.522(5) no . 1_556 C4 C7 3.383(3) no . 2_645 C4 C7 3.383(3) no . 2_655 C5 O10 3.350(5) no . 6_565 C5 C7 3.452(3) no . 2_645 C5 C7 3.452(3) no . 2_655 C7 C4 3.383(3) no . 2_644 C7 C4 3.383(3) no . 2_654 C7 C5 3.452(3) no . 2_644 C7 C5 3.452(3) no . 2_654 C10 O10 3.181(3) no . 5_665 C10 O10 3.181(3) no . 5_675 C10 C10 3.567(4) no . 5_665 C10 C10 3.567(4) no . 5_675 C13 C13 3.586(4) no . 5_664 C13 C13 3.586(4) no . 5_674 C14 O10 3.223(6) no . 1_554 C14 O11 3.322(3) no . 5_664 C14 O11 3.322(3) no . 5_674 O9 H7 2.2326 no . . O10 H12A 2.6190 no . . O10 H12A 2.6190 no . 3_565 O10 H12B 2.6190 no . . O10 H12B 2.6190 no . 3_565 N8 H2 2.6038 no . . C1 H3 3.2623 no . . C1 H5 3.2886 no . . C2 H4 3.2580 no . . C2 H6 3.2780 no . . C2 H7 3.3549 no . . C3 H5 3.2636 no . . C4 H2 3.2616 no . . C4 H6 3.2579 no . . C5 H3 3.2603 no . . C6 H2 3.2810 no . . C6 H4 3.2592 no . . C6 H7 2.6447 no . . C7 H2 2.6927 no . . C7 H6 2.6269 no . . C10 H7 3.5727 no . . C10 H12A 2.5776 no . . C10 H12A 2.5776 no . 3_565 C10 H12B 2.5776 no . . C10 H12B 2.5776 no . 3_565 C14 H12A 3.1438 no . . C14 H12A 3.1438 no . 3_565 C14 H12B 3.1438 no . . C14 H12B 3.1438 no . 3_565 H2 H3 2.3251 no . . H3 H4 2.3301 no . . H4 H5 2.3344 no . . H5 H6 2.3477 no . . H6 H7 2.4413 no . . O9 H3 2.6302 no . 1_554 O9 H5 3.2731 no . 2_644 O9 H5 3.2731 no . 2_654 O9 H12A 3.5904 no . 5_675 O9 H12A 3.5904 no . 7_645 O9 H12B 3.5904 no . 5_665 O9 H12B 3.5904 no . 7_655 O10 H5 2.4011 no . 6_465 O10 H14 2.2808 no . 1_556 O11 H2 3.2723 no . 1_554 O11 H3 2.7375 no . 1_554 O11 H14 3.1295 no . 5_664 O11 H14 3.1295 no . 5_674 N8 H5 3.4004 no . 2_644 N8 H5 3.4004 no . 2_654 N8 H12A 2.7041 no . 5_675 N8 H12A 2.7041 no . 7_645 N8 H12B 2.7041 no . 5_665 N8 H12B 2.7041 no . 7_655 N8 H14 3.1429 no . 1_556 C1 H4 3.2248 no . 2_644 C1 H4 3.2248 no . 2_654 C1 H12A 3.3224 no . 5_675 C1 H12A 3.3224 no . 7_645 C1 H12B 3.3224 no . 5_665 C1 H12B 3.3224 no . 7_655 C2 H12A 3.1075 no . 5_675 C2 H12A 3.1075 no . 7_645 C2 H12B 3.1075 no . 5_665 C2 H12B 3.1075 no . 7_655 C3 H6 3.3315 no . 2_645 C3 H6 3.3315 no . 2_655 C4 H6 3.4865 no . 2_645 C4 H6 3.4865 no . 2_655 C4 H7 3.2091 no . 2_645 C4 H7 3.2091 no . 2_655 C4 H12A 3.5681 no . 6_565 C4 H12A 3.5681 no . 8_555 C4 H12B 3.5681 no . 6_565 C4 H12B 3.5681 no . 8_555 C5 H7 3.1732 no . 2_645 C5 H7 3.1732 no . 2_655 C5 H12A 3.5628 no . 6_565 C5 H12A 3.5628 no . 8_555 C5 H12B 3.5628 no . 6_565 C5 H12B 3.5628 no . 8_555 C5 H14 3.5349 no . 6_564 C6 H3 3.5698 no . 2_644 C6 H3 3.5698 no . 2_654 C6 H4 3.4003 no . 2_644 C6 H4 3.4003 no . 2_654 C6 H14 3.5792 no . 6_564 C7 H4 3.2797 no . 2_644 C7 H4 3.2797 no . 2_654 C7 H5 3.4020 no . 2_644 C7 H5 3.4020 no . 2_654 C7 H12A 3.1409 no . 5_675 C7 H12A 3.1409 no . 7_645 C7 H12B 3.1409 no . 5_665 C7 H12B 3.1409 no . 7_655 C10 H3 3.2835 no . 1_554 C10 H5 3.4426 no . 6_465 C10 H14 3.2808 no . 1_556 C10 H14 3.4626 no . 5_664 C10 H14 3.4626 no . 5_674 C12 H2 3.4311 no . 5_665 C12 H2 3.4311 no . 5_675 C12 H4 3.3801 no . 6_465 C12 H5 3.3573 no . 6_465 C12 H14 3.5936 no . 5_664 C12 H14 3.5936 no . 5_674 C13 H2 3.0866 no . 1_554 C13 H2 3.3534 no . 5_665 C13 H2 3.3534 no . 5_675 C13 H6 3.5590 no . 6_464 C14 H2 2.9608 no . 1_554 C14 H6 3.0564 no . 6_464 C14 H12A 3.3813 no . 5_674 C14 H12A 3.3813 no . 7_644 C14 H12B 3.3813 no . 5_664 C14 H12B 3.3813 no . 7_654 H2 O11 3.2723 no . 1_556 H2 C12 3.4311 no . 5_665 H2 C12 3.4311 no . 5_675 H2 C13 3.0866 no . 1_556 H2 C13 3.3534 no . 5_665 H2 C13 3.3534 no . 5_675 H2 C14 2.9608 no . 1_556 H2 H12A 2.7054 no . 5_675 H2 H12A 2.7054 no . 7_645 H2 H12B 2.7054 no . 5_665 H2 H12B 2.7054 no . 7_655 H2 H14 3.1931 no . 1_556 H3 O9 2.6302 no . 1_556 H3 O11 2.7375 no . 1_556 H3 C6 3.5698 no . 2_645 H3 C6 3.5698 no . 2_655 H3 C10 3.2835 no . 1_556 H3 H6 3.2135 no . 2_645 H3 H6 3.2135 no . 2_655 H3 H7 3.2873 no . 1_556 H4 C1 3.2248 no . 2_645 H4 C1 3.2248 no . 2_655 H4 C6 3.4003 no . 2_645 H4 C6 3.4003 no . 2_655 H4 C7 3.2797 no . 2_645 H4 C7 3.2797 no . 2_655 H4 C12 3.3801 no . 6_565 H4 H6 3.4792 no . 2_645 H4 H6 3.4792 no . 2_655 H4 H7 3.3073 no . 1_556 H4 H7 3.3702 no . 2_645 H4 H7 3.3702 no . 2_655 H4 H12A 2.9470 no . 6_565 H4 H12A 2.9470 no . 8_555 H4 H12B 2.9470 no . 6_565 H4 H12B 2.9470 no . 8_555 H5 O9 3.2731 no . 2_645 H5 O9 3.2731 no . 2_655 H5 O10 2.4011 no . 6_565 H5 N8 3.4004 no . 2_645 H5 N8 3.4004 no . 2_655 H5 C7 3.4020 no . 2_645 H5 C7 3.4020 no . 2_655 H5 C10 3.4426 no . 6_565 H5 C12 3.3573 no . 6_565 H5 H7 3.3144 no . 2_645 H5 H7 3.3144 no . 2_655 H5 H12A 2.9435 no . 6_565 H5 H12A 2.9435 no . 8_555 H5 H12B 2.9435 no . 6_565 H5 H12B 2.9435 no . 8_555 H5 H14 2.8709 no . 6_564 H6 C3 3.3315 no . 2_644 H6 C3 3.3315 no . 2_654 H6 C4 3.4865 no . 2_644 H6 C4 3.4865 no . 2_654 H6 C13 3.5590 no . 6_564 H6 C14 3.0564 no . 6_564 H6 H3 3.2135 no . 2_644 H6 H3 3.2135 no . 2_654 H6 H4 3.4792 no . 2_644 H6 H4 3.4792 no . 2_654 H6 H14 2.9554 no . 6_564 H7 C4 3.2091 no . 2_644 H7 C4 3.2091 no . 2_654 H7 C5 3.1732 no . 2_644 H7 C5 3.1732 no . 2_654 H7 H3 3.2873 no . 1_554 H7 H4 3.3073 no . 1_554 H7 H4 3.3702 no . 2_644 H7 H4 3.3702 no . 2_654 H7 H5 3.3144 no . 2_644 H7 H5 3.3144 no . 2_654 H12A O9 3.5904 no . 5_675 H12A N8 2.7041 no . 5_675 H12A C1 3.3224 no . 5_675 H12A C2 3.1075 no . 5_675 H12A C4 3.5681 no . 6_465 H12A C5 3.5628 no . 6_465 H12A C7 3.1409 no . 5_675 H12A C14 3.3813 no . 5_674 H12A H2 2.7054 no . 5_675 H12A H4 2.9470 no . 6_465 H12A H5 2.9435 no . 6_465 H12A H14 3.2316 no . 5_674 H12B O9 3.5904 no . 5_665 H12B N8 2.7041 no . 5_665 H12B C1 3.3224 no . 5_665 H12B C2 3.1075 no . 5_665 H12B C4 3.5681 no . 6_465 H12B C5 3.5628 no . 6_465 H12B C7 3.1409 no . 5_665 H12B C14 3.3813 no . 5_664 H12B H2 2.7054 no . 5_665 H12B H4 2.9470 no . 6_465 H12B H5 2.9435 no . 6_465 H12B H14 3.2316 no . 5_664 H14 O10 2.2808 no . 1_554 H14 O11 3.1295 no . 5_664 H14 O11 3.1295 no . 5_674 H14 N8 3.1429 no . 1_554 H14 C5 3.5349 no . 6_464 H14 C6 3.5792 no . 6_464 H14 C10 3.2808 no . 1_554 H14 C10 3.4626 no . 5_664 H14 C10 3.4626 no . 5_674 H14 C12 3.5936 no . 5_664 H14 C12 3.5936 no . 5_674 H14 H2 3.1931 no . 1_554 H14 H5 2.8709 no . 6_464 H14 H6 2.9554 no . 6_464 H14 H12A 3.2316 no . 5_674 H14 H12A 3.2316 no . 7_644 H14 H12B 3.2316 no . 5_664 H14 H12B 3.2316 no . 7_654 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================