# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 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_ThyAcetate_Cmpd3 _database_code_depnum_ccdc_archive 'CCDC 888370' #TrackingRef '12132_web_deposit_cif_file_0_PriscillaJohnston_1340593910.ThyAcetate_Cmpd3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Thymine Acetate ; _chemical_name_common ThyAcetate _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N2 O4' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.0700(10) _cell_length_b 22.070(4) _cell_length_c 8.3100(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.85(3) _cell_angle_gamma 90.00 _cell_volume 913.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9977 _exptl_absorpt_correction_T_max 0.9977 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71068 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'MX1 Beamline, Australian Synchrotron' _diffrn_radiation_monochromator 'silicone double crystal' _diffrn_measurement_device_type '\f goniostat with quantum 210r detector' _diffrn_measurement_method 'f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5903 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1526 _reflns_number_gt 1349 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu Ice' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material CIFTAB _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^)+(0.0664P)^2^+0.7331P] 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 1526 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.6049(3) 0.16466(7) 0.89385(19) 0.0121(4) Uani 1 1 d . . . C2 C 0.8263(4) 0.13786(8) 0.9888(2) 0.0133(4) Uani 1 1 d . . . N3 N 0.8431(3) 0.07620(7) 0.9668(2) 0.0151(4) Uani 1 1 d . . . C4 C 0.6617(4) 0.04011(8) 0.8657(2) 0.0139(4) Uani 1 1 d . . . C5 C 0.4327(4) 0.07139(8) 0.7708(2) 0.0137(4) Uani 1 1 d . . . C6 C 0.4164(4) 0.13162(8) 0.7894(2) 0.0120(4) Uani 1 1 d . . . H6 H 0.2671 0.1524 0.7272 0.014 Uiso 1 1 calc R . . O7 O 0.9924(3) 0.16664(6) 1.08280(17) 0.0193(4) Uani 1 1 d . . . O8 O 0.6997(3) -0.01500(6) 0.85889(18) 0.0202(4) Uani 1 1 d . . . C9 C 0.2274(4) 0.03550(9) 0.6563(3) 0.0203(5) Uani 1 1 d . . . H9A H 0.0835 0.0625 0.6033 0.030 Uiso 1 1 calc R . . H9B H 0.1522 0.0042 0.7180 0.030 Uiso 1 1 calc R . . H9C H 0.3124 0.0164 0.5726 0.030 Uiso 1 1 calc R . . C10 C 0.5813(4) 0.23028(8) 0.9086(2) 0.0127(4) Uani 1 1 d . . . H10A H 0.5787 0.2409 1.0240 0.015 Uiso 1 1 calc R . . H10B H 0.4099 0.2440 0.8407 0.015 Uiso 1 1 calc R . . C11 C 0.8119(4) 0.26246(8) 0.8540(2) 0.0112(4) Uani 1 1 d . . . O12 O 0.9465(3) 0.24169(6) 0.76258(16) 0.0159(4) Uani 1 1 d . . . O13 O 0.8385(3) 0.31782(6) 0.91885(16) 0.0161(4) Uani 1 1 d . . . C14 C 1.0297(5) 0.35712(9) 0.8612(3) 0.0224(5) Uani 1 1 d . . . H14A H 1.2100 0.3396 0.8904 0.034 Uiso 1 1 calc R . . H14B H 1.0275 0.3971 0.9122 0.034 Uiso 1 1 calc R . . H14C H 0.9809 0.3612 0.7418 0.034 Uiso 1 1 calc R . . H1 H 0.977(5) 0.0586(11) 1.025(3) 0.020(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0133(9) 0.0101(8) 0.0131(8) 0.0010(6) 0.0026(6) 0.0012(6) C2 0.0158(11) 0.0121(9) 0.0122(9) 0.0017(7) 0.0036(8) 0.0006(7) N3 0.0133(9) 0.0105(8) 0.0195(9) 0.0024(6) -0.0018(7) 0.0028(6) C4 0.0147(11) 0.0114(9) 0.0161(9) 0.0019(7) 0.0043(8) -0.0006(7) C5 0.0122(10) 0.0141(9) 0.0149(9) 0.0003(7) 0.0030(8) 0.0005(7) C6 0.0102(10) 0.0143(9) 0.0120(9) 0.0027(7) 0.0030(8) 0.0012(7) O7 0.0191(8) 0.0150(7) 0.0201(7) -0.0026(5) -0.0059(6) -0.0009(6) O8 0.0170(8) 0.0095(7) 0.0317(8) 0.0000(6) -0.0015(6) 0.0021(5) C9 0.0173(11) 0.0165(10) 0.0248(11) -0.0034(8) -0.0017(9) -0.0007(8) C10 0.0142(10) 0.0087(9) 0.0154(9) -0.0013(7) 0.0032(7) 0.0030(7) C11 0.0127(10) 0.0102(9) 0.0090(8) 0.0003(7) -0.0023(7) 0.0036(7) O12 0.0171(8) 0.0139(7) 0.0181(7) 0.0010(5) 0.0073(6) 0.0048(5) O13 0.0218(8) 0.0098(6) 0.0172(7) -0.0034(5) 0.0049(6) -0.0025(5) C14 0.0232(12) 0.0122(10) 0.0325(12) -0.0002(8) 0.0074(9) -0.0056(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.373(2) . ? N1 C2 1.378(3) . ? N1 C10 1.460(2) . ? C2 O7 1.214(2) . ? C2 N3 1.378(2) . ? N3 C4 1.377(3) . ? C4 O8 1.234(2) . ? C4 C5 1.450(3) . ? C5 C6 1.343(3) . ? C5 C9 1.498(3) . ? C10 C11 1.509(3) . ? C11 O12 1.203(2) . ? C11 O13 1.332(2) . ? O13 C14 1.448(2) . ? 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 C6 N1 C2 121.94(15) . . ? C6 N1 C10 121.41(15) . . ? C2 N1 C10 116.65(15) . . ? O7 C2 N3 123.32(17) . . ? O7 C2 N1 122.35(17) . . ? N3 C2 N1 114.33(16) . . ? C4 N3 C2 126.98(16) . . ? O8 C4 N3 120.40(17) . . ? O8 C4 C5 124.06(17) . . ? N3 C4 C5 115.53(17) . . ? C6 C5 C4 117.98(17) . . ? C6 C5 C9 123.12(17) . . ? C4 C5 C9 118.89(17) . . ? C5 C6 N1 123.22(16) . . ? N1 C10 C11 111.18(15) . . ? O12 C11 O13 125.35(17) . . ? O12 C11 C10 125.04(17) . . ? O13 C11 C10 109.58(15) . . ? C11 O13 C14 116.01(15) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.287 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.057 data_ThyPropOate_Cmpd5 _database_code_depnum_ccdc_archive 'CCDC 888371' #TrackingRef '12133_web_deposit_cif_file_1_PriscillaJohnston_1340593910.ThyPropOate_Cmpd5_.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ThyPropOate ; _chemical_name_common ThyPropOate _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 N2 O4' _chemical_formula_sum 'C9 H12 N2 O4' _chemical_formula_weight 212.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.9270(18) _cell_length_b 14.369(3) _cell_length_c 7.7640(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.60(3) _cell_angle_gamma 90.00 _cell_volume 995.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9978 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71253 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'MX1 Beamline, Australian Synchrotron' _diffrn_radiation_monochromator 'silicon double crystal' _diffrn_measurement_device_type '\f goniostat with quantum 210r detector' _diffrn_measurement_method 'f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12566 _diffrn_reflns_av_R_equivalents 0.2761 _diffrn_reflns_av_sigmaI/netI 0.1631 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1702 _reflns_number_gt 1572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu Ice' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material CIFTAB _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^)+(0.1114P)^2^+0.3181P] 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 0.22(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1702 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.2106 _refine_ls_wR_factor_gt 0.2074 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 O8 O 0.62738(16) 0.08222(10) 0.08130(18) 0.0149(5) Uani 1 1 d . . . O7 O 0.20406(15) -0.02422(10) 0.33386(18) 0.0142(5) Uani 1 1 d . . . O13 O 0.22423(17) 0.28190(11) 0.6665(2) 0.0192(5) Uani 1 1 d . . . N3 N 0.41948(19) 0.02853(11) 0.2139(2) 0.0090(5) Uani 1 1 d . . . O14 O 0.01053(17) 0.29161(10) 0.5139(2) 0.0160(5) Uani 1 1 d . . . N1 N 0.34312(19) 0.08449(12) 0.4785(2) 0.0095(5) Uani 1 1 d . . . C10 C 0.2347(2) 0.08464(14) 0.6194(3) 0.0118(6) Uani 1 1 d . . . H10A H 0.2832 0.1102 0.7244 0.014 Uiso 1 1 calc R . . H10B H 0.2044 0.0198 0.6443 0.014 Uiso 1 1 calc R . . C4 C 0.5430(2) 0.08590(13) 0.2055(3) 0.0091(6) Uani 1 1 d . . . C6 C 0.4644(2) 0.14351(13) 0.4792(2) 0.0093(6) Uani 1 1 d . . . H6 H 0.4778 0.1837 0.5753 0.011 Uiso 1 1 calc R . . C5 C 0.5654(2) 0.14771(14) 0.3518(3) 0.0100(6) Uani 1 1 d . . . C2 C 0.3139(2) 0.02630(14) 0.3411(3) 0.0094(6) Uani 1 1 d . . . C12 C 0.1216(2) 0.24499(14) 0.5913(2) 0.0096(6) Uani 1 1 d . . . C11 C 0.0962(2) 0.14176(14) 0.5765(3) 0.0109(6) Uani 1 1 d . . . H11A H 0.0631 0.1271 0.4574 0.013 Uiso 1 1 calc R . . H11B H 0.0146 0.1236 0.6551 0.013 Uiso 1 1 calc R . . C9 C 0.6998(2) 0.21010(15) 0.3556(3) 0.0155(6) Uani 1 1 d . . . H9A H 0.6884 0.2565 0.4469 0.023 Uiso 1 1 calc R . . H9B H 0.7088 0.2416 0.2443 0.023 Uiso 1 1 calc R . . H9C H 0.7899 0.1729 0.3780 0.023 Uiso 1 1 calc R . . C15 C 0.0139(3) 0.39133(14) 0.5305(3) 0.0171(6) Uani 1 1 d . . . H15A H 0.0028 0.4084 0.6519 0.026 Uiso 1 1 calc R . . H15B H -0.0684 0.4185 0.4627 0.026 Uiso 1 1 calc R . . H15C H 0.1097 0.4150 0.4882 0.026 Uiso 1 1 calc R . . H3 H 0.406(3) -0.009(2) 0.129(4) 0.020(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O8 0.0161(9) 0.0158(10) 0.0130(9) -0.0049(5) 0.0027(7) -0.0058(6) O7 0.0131(9) 0.0104(9) 0.0192(9) -0.0005(6) -0.0007(6) -0.0062(5) O13 0.0158(9) 0.0125(10) 0.0291(10) -0.0047(6) -0.0097(7) -0.0001(6) N3 0.0118(10) 0.0048(10) 0.0103(9) -0.0020(7) -0.0019(7) -0.0013(6) O14 0.0151(9) 0.0080(9) 0.0247(9) -0.0029(6) -0.0070(6) 0.0015(6) N1 0.0114(10) 0.0068(10) 0.0101(9) 0.0005(6) -0.0016(7) 0.0007(6) C10 0.0148(12) 0.0096(12) 0.0110(11) 0.0033(7) 0.0014(8) 0.0006(7) C4 0.0089(11) 0.0055(11) 0.0128(11) 0.0005(7) -0.0040(8) 0.0001(7) C6 0.0119(11) 0.0063(11) 0.0096(10) -0.0010(7) -0.0057(8) 0.0019(7) C5 0.0120(11) 0.0058(11) 0.0121(10) 0.0001(7) -0.0047(8) 0.0009(7) C2 0.0097(11) 0.0049(11) 0.0134(11) 0.0030(7) -0.0037(8) 0.0015(7) C12 0.0109(11) 0.0094(12) 0.0085(10) -0.0014(7) 0.0007(8) -0.0008(7) C11 0.0088(11) 0.0096(11) 0.0142(11) -0.0001(7) -0.0006(8) -0.0029(7) C9 0.0140(12) 0.0153(12) 0.0171(12) -0.0049(8) -0.0009(9) -0.0056(8) C15 0.0215(12) 0.0086(12) 0.0209(12) -0.0015(8) -0.0033(9) 0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O8 C4 1.231(3) . ? O7 C2 1.221(3) . ? O13 C12 1.204(2) . ? N3 C2 1.373(3) . ? N3 C4 1.379(3) . ? N3 H3 0.86(3) . ? O14 C12 1.335(2) . ? O14 C15 1.439(3) . ? N1 C6 1.375(3) . ? N1 C2 1.378(3) . ? N1 C10 1.468(3) . ? C10 C11 1.518(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C4 C5 1.454(3) . ? C6 C5 1.347(3) . ? C6 H6 0.9500 . ? C5 C9 1.497(3) . ? C12 C11 1.505(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 N3 C4 127.15(17) . . ? C2 N3 H3 116.1(17) . . ? C4 N3 H3 116.7(17) . . ? C12 O14 C15 116.39(16) . . ? C6 N1 C2 121.33(17) . . ? C6 N1 C10 121.42(16) . . ? C2 N1 C10 117.16(17) . . ? N1 C10 C11 112.29(16) . . ? N1 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N1 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? O8 C4 N3 120.53(18) . . ? O8 C4 C5 123.92(18) . . ? N3 C4 C5 115.54(19) . . ? C5 C6 N1 123.90(18) . . ? C5 C6 H6 118.1 . . ? N1 C6 H6 118.1 . . ? C6 C5 C4 117.33(18) . . ? C6 C5 C9 123.68(18) . . ? C4 C5 C9 118.97(18) . . ? O7 C2 N3 122.55(18) . . ? O7 C2 N1 122.82(19) . . ? N3 C2 N1 114.63(17) . . ? O13 C12 O14 123.73(19) . . ? O13 C12 C11 125.79(18) . . ? O14 C12 C11 110.44(16) . . ? C12 C11 C10 113.20(16) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O14 C15 H15A 109.5 . . ? O14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 C6 N1 C10 C11 98.0(2) . . . . ? C2 N1 C10 C11 -78.6(2) . . . . ? C2 N3 C4 O8 -178.23(17) . . . . ? C2 N3 C4 C5 2.7(3) . . . . ? C2 N1 C6 C5 -2.1(3) . . . . ? C10 N1 C6 C5 -178.51(17) . . . . ? N1 C6 C5 C4 0.2(3) . . . . ? N1 C6 C5 C9 -178.14(18) . . . . ? O8 C4 C5 C6 -179.42(18) . . . . ? N3 C4 C5 C6 -0.4(3) . . . . ? O8 C4 C5 C9 -1.0(3) . . . . ? N3 C4 C5 C9 178.01(17) . . . . ? C4 N3 C2 O7 176.59(18) . . . . ? C4 N3 C2 N1 -4.4(3) . . . . ? C6 N1 C2 O7 -177.13(18) . . . . ? C10 N1 C2 O7 -0.5(3) . . . . ? C6 N1 C2 N3 3.9(3) . . . . ? C10 N1 C2 N3 -179.53(15) . . . . ? C15 O14 C12 O13 -2.8(3) . . . . ? C15 O14 C12 C11 175.00(16) . . . . ? O13 C12 C11 C10 -17.2(3) . . . . ? O14 C12 C11 C10 165.09(16) . . . . ? N1 C10 C11 C12 -77.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.434 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.124 data_ThyPropOic_Cmpd6 _database_code_depnum_ccdc_archive 'CCDC 888372' #TrackingRef '12134_web_deposit_cif_file_2_PriscillaJohnston_1340593910.ThyPropOic_Cmpd6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Thymine propanoic acid ; _chemical_name_common 'Thymine PropOic' _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N2 O4' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.9130(10) _cell_length_b 20.405(4) _cell_length_c 8.5920(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.90(3) _cell_angle_gamma 90.00 _cell_volume 842.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9949 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71072 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'MX1 Beamline, Australian Synchrotron' _diffrn_radiation_monochromator 'silicone double crystal' _diffrn_measurement_device_type '\f goniostat with quantum 210r detector' _diffrn_measurement_method 'f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8717 _diffrn_reflns_av_R_equivalents 0.1273 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1336 _reflns_number_gt 1245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu Ice' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material CIFTAB _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^)+(0.0885P)^2^+0.5739P] 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 1336 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.6393(3) 0.16465(7) 0.77830(16) 0.0143(4) Uani 1 1 d . . . O2 O 0.4448(3) 0.37968(7) 1.07087(15) 0.0136(4) Uani 1 1 d . . . O3 O 0.9970(3) 0.49301(7) 0.80099(16) 0.0138(5) Uani 1 1 d . . . O4 O 0.4257(3) 0.23323(7) 0.58997(16) 0.0147(4) Uani 1 1 d . . . N5 N 0.7147(4) 0.43591(8) 0.93116(19) 0.0103(5) Uani 1 1 d . . . N6 N 0.3950(3) 0.35974(7) 0.80360(18) 0.0078(5) Uani 1 1 d . . . C7 C 0.4658(4) 0.21360(9) 0.7258(2) 0.0094(5) Uani 1 1 d . . . C8 C 0.3247(4) 0.24130(9) 0.8509(2) 0.0086(5) Uani 1 1 d . . . H8A H 0.4636 0.2457 0.9517 0.010 Uiso 1 1 calc R . . H8B H 0.1806 0.2100 0.8695 0.010 Uiso 1 1 calc R . . C9 C 0.7413(4) 0.43746(9) 0.4942(2) 0.0116(5) Uani 1 1 d . . . H9A H 0.9310 0.4224 0.4952 0.017 Uiso 1 1 calc R . . H9B H 0.7312 0.4850 0.4784 0.017 Uiso 1 1 calc R . . H9C H 0.6116 0.4159 0.4075 0.017 Uiso 1 1 calc R . . C10 C 0.5122(4) 0.39124(9) 0.9432(2) 0.0089(5) Uani 1 1 d . . . C11 C 0.1894(4) 0.30774(9) 0.8068(2) 0.0084(5) Uani 1 1 d . . . H11A H 0.0645 0.3046 0.7008 0.010 Uiso 1 1 calc R . . H11B H 0.0746 0.3195 0.8848 0.010 Uiso 1 1 calc R . . C12 C 0.4682(4) 0.37651(9) 0.6622(2) 0.0089(5) Uani 1 1 d . . . H12 H 0.3736 0.3555 0.5678 0.011 Uiso 1 1 calc R . . C13 C 0.8072(4) 0.45326(9) 0.7948(2) 0.0095(5) Uani 1 1 d . . . C14 C 0.6651(4) 0.42081(9) 0.6499(2) 0.0087(5) Uani 1 1 d . . . H7 H 0.727(7) 0.1471(14) 0.699(4) 0.039(8) Uiso 1 1 d . . . H1 H 0.788(6) 0.4556(14) 1.014(3) 0.025(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 0.0165(9) 0.0177(8) 0.0075(7) 0.0012(5) -0.0006(6) 0.0076(6) O2 0.0173(9) 0.0191(8) 0.0042(7) -0.0019(5) 0.0019(6) -0.0049(6) O3 0.0142(9) 0.0177(8) 0.0087(8) -0.0019(5) 0.0005(6) -0.0077(6) O4 0.0195(9) 0.0189(8) 0.0055(7) 0.0029(5) 0.0020(6) 0.0051(6) N5 0.0128(10) 0.0131(9) 0.0042(9) -0.0029(6) -0.0004(7) -0.0035(6) N6 0.0089(9) 0.0110(8) 0.0033(8) -0.0001(6) 0.0010(7) -0.0011(6) C7 0.0082(10) 0.0095(9) 0.0086(10) -0.0014(7) -0.0026(8) -0.0031(7) C8 0.0075(11) 0.0128(10) 0.0046(9) 0.0002(7) -0.0011(8) -0.0013(7) C9 0.0134(12) 0.0144(10) 0.0067(10) 0.0009(7) 0.0012(8) -0.0018(7) C10 0.0092(10) 0.0115(9) 0.0045(10) -0.0013(7) -0.0022(8) 0.0022(7) C11 0.0076(10) 0.0130(10) 0.0036(9) -0.0013(7) -0.0011(8) -0.0010(7) C12 0.0103(11) 0.0103(9) 0.0050(9) 0.0004(7) -0.0014(8) 0.0027(7) C13 0.0099(10) 0.0110(9) 0.0070(10) 0.0004(7) 0.0000(8) 0.0017(7) C14 0.0089(10) 0.0104(9) 0.0052(10) 0.0012(7) -0.0020(8) 0.0028(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 O1 C7 1.330(2) . ? O2 C10 1.232(2) . ? O3 C13 1.229(2) . ? O4 C7 1.211(2) . ? N5 C10 1.369(3) . ? N5 C13 1.387(3) . ? N6 C10 1.378(2) . ? N6 C12 1.379(3) . ? N6 C11 1.469(2) . ? C7 C8 1.504(3) . ? C8 C11 1.523(3) . ? C9 C14 1.501(3) . ? C12 C14 1.344(3) . ? C13 C14 1.455(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N5 C13 127.12(16) . . ? C10 N6 C12 120.86(17) . . ? C10 N6 C11 119.09(15) . . ? C12 N6 C11 120.05(15) . . ? O4 C7 O1 122.8(2) . . ? O4 C7 C8 123.84(18) . . ? O1 C7 C8 113.40(16) . . ? C7 C8 C11 113.48(16) . . ? O2 C10 N5 121.84(17) . . ? O2 C10 N6 123.01(18) . . ? N5 C10 N6 115.14(17) . . ? N6 C11 C8 112.40(16) . . ? C14 C12 N6 123.96(17) . . ? O3 C13 N5 120.63(17) . . ? O3 C13 C14 124.32(18) . . ? N5 C13 C14 115.04(18) . . ? C12 C14 C13 117.73(17) . . ? C12 C14 C9 122.57(17) . . ? C13 C14 C9 119.70(17) . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.308 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.073 data_ThyPropAmide_Cmpd7 _database_code_depnum_ccdc_archive 'CCDC 888373' #TrackingRef '12135_web_deposit_cif_file_3_PriscillaJohnston_1340593910.ThyPropAmide_Cmpd7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ThyPropAmide ; _chemical_name_common ThyPropAmide _chemical_melting_point ? _chemical_formula_moiety 'C8 H11 N3 O3' _chemical_formula_sum 'C8 H11 N3 O3' _chemical_formula_weight 197.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 7.3571(15) _cell_length_b 15.243(3) _cell_length_c 15.854(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.18(3) _cell_angle_gamma 90.00 _cell_volume 1777.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12491 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10151 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2947 _reflns_number_gt 2350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material CIFTAB _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^)+(0.0372P)^2^+0.5800P] 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 2947 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1424(2) 0.41873(10) 0.23575(10) 0.0237(4) Uani 1 1 d . . . O3 O 0.22019(17) 0.50728(8) 0.34520(8) 0.0303(3) Uani 1 1 d . . . O5 O 0.07773(17) 0.33222(8) 0.12193(8) 0.0292(3) Uani 1 1 d . . . N7 N 0.04326(19) 0.27571(9) 0.25420(9) 0.0212(3) Uani 1 1 d . . . N11 N 0.4439(2) 0.09949(10) 0.25578(11) 0.0252(4) Uani 1 1 d . . . C12 C 0.1614(2) 0.43565(11) 0.32146(11) 0.0224(4) Uani 1 1 d . . . O14 O 0.19444(18) 0.07692(10) 0.33313(8) 0.0405(4) Uani 1 1 d . . . C15 C 0.2651(2) 0.10179(11) 0.26677(11) 0.0240(4) Uani 1 1 d . . . C19 C 0.0867(2) 0.34143(11) 0.19873(11) 0.0218(4) Uani 1 1 d . . . C21 C 0.1087(2) 0.36396(11) 0.37614(11) 0.0218(4) Uani 1 1 d . . . C22 C 0.0539(2) 0.28866(11) 0.34014(11) 0.0214(4) Uani 1 1 d . . . H22 H 0.0204 0.2415 0.3761 0.026 Uiso 1 1 calc R . . C23 C -0.0108(2) 0.18948(11) 0.22015(11) 0.0247(4) Uani 1 1 d . . . H23A H -0.0917 0.1983 0.1709 0.030 Uiso 1 1 calc R . . H23B H -0.0800 0.1570 0.2636 0.030 Uiso 1 1 calc R . . C26 C 0.1522(2) 0.13535(11) 0.19367(11) 0.0248(4) Uani 1 1 d . . . H26A H 0.1092 0.0847 0.1601 0.030 Uiso 1 1 calc R . . H26B H 0.2305 0.1716 0.1568 0.030 Uiso 1 1 calc R . . C27 C 0.1184(3) 0.37538(12) 0.47009(11) 0.0298(5) Uani 1 1 d . . . H27A H 0.0887 0.3197 0.4977 0.045 Uiso 1 1 calc R . . H27B H 0.0314 0.4205 0.4876 0.045 Uiso 1 1 calc R . . H27C H 0.2416 0.3934 0.4863 0.045 Uiso 1 1 calc R . . O2 O 0.42879(17) 0.71216(8) 0.38330(8) 0.0275(3) Uani 1 1 d . . . O4 O 0.29856(16) 0.95432(8) 0.60964(8) 0.0298(3) Uani 1 1 d . . . N6 N 0.3641(2) 0.61563(10) 0.48865(10) 0.0243(4) Uani 1 1 d . . . O8 O 0.3100(2) 0.51445(8) 0.59001(8) 0.0410(4) Uani 1 1 d . . . N9 N 0.46201(19) 0.75649(9) 0.52023(9) 0.0219(3) Uani 1 1 d . . . N10 N 0.0592(2) 0.90399(10) 0.53541(11) 0.0275(4) Uani 1 1 d . . . C13 C 0.3545(2) 0.90177(11) 0.46904(11) 0.0245(4) Uani 1 1 d . . . H13A H 0.3984 0.9574 0.4441 0.029 Uiso 1 1 calc R . . H13B H 0.2817 0.8708 0.4257 0.029 Uiso 1 1 calc R . . C16 C 0.2345(2) 0.92232(10) 0.54384(11) 0.0216(4) Uani 1 1 d . . . C17 C 0.5173(2) 0.84523(11) 0.49311(12) 0.0249(4) Uani 1 1 d . . . H17A H 0.5997 0.8403 0.4441 0.030 Uiso 1 1 calc R . . H17B H 0.5851 0.8741 0.5395 0.030 Uiso 1 1 calc R . . C18 C 0.3992(2) 0.65661(11) 0.63372(11) 0.0229(4) Uani 1 1 d . . . C20 C 0.4189(2) 0.69607(11) 0.45895(11) 0.0215(4) Uani 1 1 d . . . C24 C 0.3540(2) 0.58940(11) 0.57259(11) 0.0250(4) Uani 1 1 d . . . C25 C 0.4500(2) 0.73562(11) 0.60486(11) 0.0231(4) Uani 1 1 d . . . H25 H 0.4794 0.7798 0.6449 0.028 Uiso 1 1 calc R . . C1 C 0.3882(3) 0.63385(12) 0.72549(11) 0.0292(4) Uani 1 1 d . . . H1A H 0.4107 0.6865 0.7594 0.044 Uiso 1 1 calc R . . H1B H 0.4798 0.5893 0.7390 0.044 Uiso 1 1 calc R . . H1C H 0.2669 0.6108 0.7381 0.044 Uiso 1 1 calc R . . H11A H 0.517(3) 0.0762(13) 0.2971(13) 0.034(6) Uiso 1 1 d . . . H10B H 0.014(3) 0.8839(13) 0.4861(14) 0.036(6) Uiso 1 1 d . . . H11B H 0.495(3) 0.1170(13) 0.2066(14) 0.041(6) Uiso 1 1 d . . . H10A H -0.017(3) 0.9173(14) 0.5805(15) 0.051(7) Uiso 1 1 d . . . H6 H 0.334(3) 0.5779(14) 0.4503(13) 0.039(6) Uiso 1 1 d . . . H1 H 0.172(3) 0.4594(14) 0.1996(13) 0.040(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0264(9) 0.0233(8) 0.0215(9) 0.0034(7) 0.0001(7) -0.0027(7) O3 0.0356(8) 0.0240(7) 0.0312(8) -0.0028(6) -0.0019(6) -0.0056(6) O5 0.0344(8) 0.0337(7) 0.0195(7) 0.0005(6) -0.0015(6) 0.0003(6) N7 0.0225(8) 0.0211(8) 0.0200(8) -0.0014(6) -0.0005(6) -0.0001(6) N11 0.0250(11) 0.0307(9) 0.0200(9) -0.0008(7) 0.0005(8) 0.0003(7) C12 0.0191(10) 0.0239(9) 0.0243(10) -0.0002(8) -0.0003(8) 0.0025(7) O14 0.0348(8) 0.0573(10) 0.0295(8) 0.0133(7) 0.0124(6) 0.0112(7) C15 0.0299(13) 0.0201(9) 0.0221(10) -0.0032(7) 0.0057(8) 0.0023(7) C19 0.0187(10) 0.0248(9) 0.0218(11) 0.0010(8) -0.0003(7) 0.0035(7) C21 0.0201(10) 0.0232(9) 0.0221(10) -0.0010(7) -0.0001(7) 0.0022(7) C22 0.0189(10) 0.0247(9) 0.0205(10) 0.0036(8) 0.0019(7) 0.0029(7) C23 0.0250(10) 0.0240(9) 0.0251(10) -0.0029(8) -0.0033(8) -0.0022(7) C26 0.0282(11) 0.0244(9) 0.0218(10) -0.0033(8) 0.0008(8) 0.0014(8) C27 0.0346(12) 0.0315(10) 0.0232(11) -0.0018(8) 0.0004(8) -0.0015(8) O2 0.0363(8) 0.0255(7) 0.0207(7) -0.0004(5) 0.0035(6) -0.0007(5) O4 0.0302(8) 0.0347(7) 0.0244(7) -0.0077(6) -0.0024(6) 0.0038(6) N6 0.0334(9) 0.0198(8) 0.0196(8) -0.0033(7) -0.0011(7) -0.0036(7) O8 0.0668(10) 0.0270(8) 0.0292(8) 0.0040(6) -0.0019(7) -0.0156(7) N9 0.0246(9) 0.0194(7) 0.0218(8) -0.0028(6) 0.0022(6) -0.0006(6) N10 0.0291(11) 0.0333(9) 0.0201(9) -0.0034(7) 0.0000(8) -0.0013(7) C13 0.0309(11) 0.0204(9) 0.0222(10) 0.0003(7) 0.0039(8) -0.0018(8) C16 0.0293(12) 0.0157(8) 0.0198(10) 0.0030(7) -0.0026(8) 0.0026(7) C17 0.0268(11) 0.0197(9) 0.0284(11) -0.0022(8) 0.0070(8) -0.0046(7) C18 0.0205(10) 0.0248(10) 0.0235(10) -0.0011(8) 0.0010(8) 0.0029(7) C20 0.0197(10) 0.0221(9) 0.0227(10) -0.0010(8) 0.0023(7) 0.0034(7) C24 0.0263(11) 0.0245(10) 0.0241(11) 0.0009(8) 0.0001(8) -0.0008(8) C25 0.0222(10) 0.0245(9) 0.0227(10) -0.0063(8) -0.0011(8) 0.0028(7) C1 0.0348(12) 0.0293(10) 0.0235(10) -0.0007(8) -0.0010(8) 0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C19 1.378(2) . ? N1 C12 1.390(2) . ? O3 C12 1.233(2) . ? O5 C19 1.227(2) . ? N7 C19 1.371(2) . ? N7 C22 1.379(2) . ? N7 C23 1.475(2) . ? N11 C15 1.328(2) . ? C12 C21 1.449(2) . ? O14 C15 1.234(2) . ? C15 C26 1.513(2) . ? C21 C22 1.343(2) . ? C21 C27 1.501(2) . ? C23 C26 1.516(2) . ? O2 C20 1.227(2) . ? O4 C16 1.243(2) . ? N6 C20 1.374(2) . ? N6 C24 1.392(2) . ? O8 C24 1.219(2) . ? N9 C20 1.375(2) . ? N9 C25 1.382(2) . ? N9 C17 1.477(2) . ? N10 C16 1.326(2) . ? C13 C16 1.513(2) . ? C13 C17 1.523(2) . ? C18 C25 1.342(2) . ? C18 C24 1.448(2) . ? C18 C1 1.498(2) . ? 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 N1 C12 127.17(16) . . ? C19 N7 C22 121.11(15) . . ? C19 N7 C23 118.64(14) . . ? C22 N7 C23 120.24(14) . . ? O3 C12 N1 119.82(16) . . ? O3 C12 C21 125.43(16) . . ? N1 C12 C21 114.75(15) . . ? O14 C15 N11 121.56(18) . . ? O14 C15 C26 121.69(17) . . ? N11 C15 C26 116.74(16) . . ? O5 C19 N7 122.74(16) . . ? O5 C19 N1 122.38(16) . . ? N7 C19 N1 114.89(16) . . ? C22 C21 C12 118.10(16) . . ? C22 C21 C27 122.27(16) . . ? C12 C21 C27 119.63(16) . . ? C21 C22 N7 123.93(16) . . ? N7 C23 C26 111.93(14) . . ? C15 C26 C23 113.87(15) . . ? C20 N6 C24 126.91(16) . . ? C20 N9 C25 121.09(14) . . ? C20 N9 C17 118.09(14) . . ? C25 N9 C17 120.80(14) . . ? C16 C13 C17 112.39(14) . . ? O4 C16 N10 122.23(17) . . ? O4 C16 C13 121.22(16) . . ? N10 C16 C13 116.55(16) . . ? N9 C17 C13 111.98(14) . . ? C25 C18 C24 118.05(16) . . ? C25 C18 C1 123.71(16) . . ? C24 C18 C1 118.24(16) . . ? O2 C20 N6 122.13(16) . . ? O2 C20 N9 122.86(16) . . ? N6 C20 N9 115.01(15) . . ? O8 C24 N6 120.06(16) . . ? O8 C24 C18 124.87(17) . . ? N6 C24 C18 115.07(16) . . ? C18 C25 N9 123.81(16) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.150 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.042 data_ButBisThyPropOic_Cmpd9 _database_code_depnum_ccdc_archive 'CCDC 888374' #TrackingRef '12136_web_deposit_cif_file_4_PriscillaJohnston_1340593910.ButBisThyPropOic_Cmpd9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ButBisThyPropOic ; _chemical_name_common ButBisThyPropOic_Compound9 _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 N4 O8, 2(H2 O)' _chemical_formula_sum 'C20 H30 N4 O10' _chemical_formula_weight 486.48 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6000(15) _cell_length_b 8.9000(18) _cell_length_c 9.4500(19) _cell_angle_alpha 96.93(3) _cell_angle_beta 111.13(3) _cell_angle_gamma 101.53(3) _cell_volume 571.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9921 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'MX1 Beamline, Australian Synchrotron' _diffrn_radiation_monochromator 'silicon double crystal' _diffrn_measurement_device_type '\f goniostat with quantum 210r detector' _diffrn_measurement_method 'f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7078 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1856 _reflns_number_gt 1687 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu Ice' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material CIFTAB _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^)+(0.0602P)^2^+0.2804P] 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 1856 _refine_ls_number_parameters 167 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2393(2) 0.34296(18) 0.40716(18) 0.0195(4) Uani 1 1 d . . . C2 C 0.2544(2) 0.3328(2) 0.5548(2) 0.0189(4) Uani 1 1 d . . . N3 N 0.2572(2) 0.46853(17) 0.64615(17) 0.0174(4) Uani 1 1 d . . . C4 C 0.2465(2) 0.6097(2) 0.5975(2) 0.0182(4) Uani 1 1 d . . . C5 C 0.2289(2) 0.6109(2) 0.4404(2) 0.0189(4) Uani 1 1 d . . . C6 C 0.2242(2) 0.4777(2) 0.3531(2) 0.0199(4) Uani 1 1 d . . . H6 H 0.2098 0.4772 0.2489 0.024 Uiso 1 1 calc R . . O7 O 0.2647(2) 0.21251(15) 0.60311(16) 0.0272(4) Uani 1 1 d . . . O8 O 0.25065(19) 0.72356(14) 0.68798(15) 0.0242(4) Uani 1 1 d . . . C9 C 0.2142(3) 0.7590(2) 0.3818(2) 0.0246(4) Uani 1 1 d . . . H9A H 0.1860 0.7387 0.2705 0.037 Uiso 1 1 calc R . . H9B H 0.3382 0.8396 0.4375 0.037 Uiso 1 1 calc R . . H9C H 0.1088 0.7957 0.3990 0.037 Uiso 1 1 calc R . . C10 C 0.2400(3) 0.2011(2) 0.3080(2) 0.0261(5) Uani 1 1 d . . . H10A H 0.3344 0.1495 0.3724 0.031 Uiso 1 1 calc R . . H10B H 0.2850 0.2331 0.2274 0.031 Uiso 1 1 calc R . . C11 C 0.0407(3) 0.0839(2) 0.2296(2) 0.0242(4) Uani 1 1 d . . . H11A H 0.0585 -0.0201 0.1971 0.029 Uiso 1 1 calc R . . H11B H -0.0198 0.0744 0.3061 0.029 Uiso 1 1 calc R . . C12 C -0.0971(3) 0.1270(2) 0.0899(2) 0.0232(4) Uani 1 1 d . . . O13 O -0.0575(2) 0.24318(15) 0.04132(16) 0.0293(4) Uani 1 1 d . . . O14 O -0.2655(2) 0.01775(16) 0.02364(17) 0.0302(4) Uani 1 1 d . . . C15 C 0.2774(2) 0.4622(2) 0.8062(2) 0.0198(4) Uani 1 1 d . . . H15A H 0.2122 0.3552 0.8089 0.024 Uiso 1 1 calc R . . H15B H 0.2113 0.5359 0.8400 0.024 Uiso 1 1 calc R . . C16 C 0.4910(2) 0.5049(2) 0.9180(2) 0.0212(4) Uani 1 1 d . . . H16A H 0.5578 0.4323 0.8837 0.025 Uiso 1 1 calc R . . H16B H 0.5559 0.6127 0.9171 0.025 Uiso 1 1 calc R . . O1W O -0.50888(19) 0.02331(15) -0.25123(16) 0.0264(4) Uani 1 1 d D . . H2W H -0.584(3) 0.095(2) -0.282(3) 0.058(8) Uiso 1 1 d D . . H3W H -0.608(3) -0.0687(17) -0.267(3) 0.057(8) Uiso 1 1 d D . . H14 H -0.339(5) 0.050(3) -0.068(4) 0.059(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0153(7) 0.0259(8) 0.0181(9) 0.0030(6) 0.0062(6) 0.0092(6) C2 0.0120(8) 0.0247(9) 0.0191(10) 0.0049(7) 0.0036(7) 0.0070(7) N3 0.0148(7) 0.0224(8) 0.0139(8) 0.0040(6) 0.0040(6) 0.0056(6) C4 0.0100(8) 0.0214(9) 0.0215(11) 0.0044(7) 0.0051(7) 0.0029(6) C5 0.0112(8) 0.0250(9) 0.0188(10) 0.0061(7) 0.0042(7) 0.0033(7) C6 0.0120(8) 0.0316(10) 0.0178(10) 0.0076(7) 0.0068(7) 0.0062(7) O7 0.0300(7) 0.0257(7) 0.0262(8) 0.0091(6) 0.0071(6) 0.0139(6) O8 0.0278(7) 0.0210(7) 0.0238(8) 0.0024(5) 0.0120(6) 0.0044(5) C9 0.0222(9) 0.0261(10) 0.0233(11) 0.0088(7) 0.0070(8) 0.0036(7) C10 0.0263(10) 0.0326(11) 0.0243(12) 0.0037(8) 0.0124(8) 0.0152(8) C11 0.0274(10) 0.0250(9) 0.0234(11) 0.0038(7) 0.0112(8) 0.0121(8) C12 0.0274(10) 0.0241(9) 0.0214(11) 0.0015(7) 0.0124(8) 0.0106(7) O13 0.0342(8) 0.0277(7) 0.0242(8) 0.0068(6) 0.0092(6) 0.0082(6) O14 0.0272(8) 0.0302(8) 0.0289(9) 0.0062(6) 0.0072(6) 0.0058(6) C15 0.0168(9) 0.0258(9) 0.0162(10) 0.0059(7) 0.0064(7) 0.0038(7) C16 0.0168(9) 0.0292(10) 0.0159(10) 0.0061(7) 0.0057(7) 0.0031(7) O1W 0.0225(7) 0.0244(7) 0.0323(8) 0.0091(6) 0.0091(6) 0.0079(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.368(2) . ? N1 C2 1.374(2) . ? N1 C10 1.481(2) . ? C2 O7 1.219(2) . ? C2 N3 1.390(2) . ? N3 C4 1.397(2) . ? N3 C15 1.474(2) . ? C4 O8 1.232(2) . ? C4 C5 1.444(3) . ? C5 C6 1.347(3) . ? C5 C9 1.499(2) . ? C10 C11 1.518(3) . ? C11 C12 1.507(3) . ? C12 O13 1.209(2) . ? C12 O14 1.324(2) . ? C15 C16 1.522(2) . ? C16 C16 1.520(3) 2_667 ? 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 C6 N1 C2 121.90(15) . . ? C6 N1 C10 121.06(15) . . ? C2 N1 C10 117.03(15) . . ? O7 C2 N1 122.38(16) . . ? O7 C2 N3 121.87(17) . . ? N1 C2 N3 115.76(15) . . ? C2 N3 C4 124.50(15) . . ? C2 N3 C15 117.04(14) . . ? C4 N3 C15 118.44(15) . . ? O8 C4 N3 119.35(16) . . ? O8 C4 C5 124.12(16) . . ? N3 C4 C5 116.53(15) . . ? C6 C5 C4 118.09(17) . . ? C6 C5 C9 123.28(17) . . ? C4 C5 C9 118.63(16) . . ? C5 C6 N1 123.20(17) . . ? N1 C10 C11 113.09(15) . . ? C12 C11 C10 113.97(16) . . ? O13 C12 O14 124.19(19) . . ? O13 C12 C11 124.68(18) . . ? O14 C12 C11 111.09(16) . . ? N3 C15 C16 111.62(14) . . ? C16 C16 C15 110.90(18) 2_667 . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.286 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.052