# 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_Compound1 _database_code_depnum_ccdc_archive 'CCDC 841955' #TrackingRef 'Compound1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Butyl-linked bis-thymine propanoate ; _chemical_name_common 'Butyl-linked bis-thymine propanoate' _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N4 O8' _chemical_formula_sum 'C22 H30 N4 O8' _chemical_formula_weight 478.50 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 9.5800(19) _cell_length_b 16.550(3) _cell_length_c 7.6900(15) _cell_angle_alpha 90.00 _cell_angle_beta 112.13(3) _cell_angle_gamma 90.00 _cell_volume 1129.4(4) _cell_formula_units_Z 2 _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 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.108 _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 15282 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.21 _reflns_number_total 2341 _reflns_number_gt 2190 _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^)+(0.0548P)^2^+0.6745P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2341 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.09954(11) -0.23336(6) 0.22747(15) 0.0232(3) Uani 1 1 d . . . N1 N 0.43698(12) -0.07274(6) 0.14148(14) 0.0144(3) Uani 1 1 d . . . C1 C -0.04277(17) -0.21600(12) 0.2441(3) 0.0341(4) Uani 1 1 d . . . H1A H -0.0326 -0.1675 0.3211 0.051 Uiso 1 1 calc R . . H1B H -0.0721 -0.2618 0.3035 0.051 Uiso 1 1 calc R . . H1C H -0.1201 -0.2069 0.1190 0.051 Uiso 1 1 calc R . . O2 O 0.08277(11) -0.11585(6) 0.07580(16) 0.0266(3) Uani 1 1 d . . . N2 N 0.65083(11) -0.01753(6) 0.37497(15) 0.0130(3) Uani 1 1 d . . . C2 C 0.15139(15) -0.17656(8) 0.14239(18) 0.0175(3) Uani 1 1 d . . . O3 O 0.65144(11) -0.14713(6) 0.27181(15) 0.0231(3) Uani 1 1 d . . . C3 C 0.30089(15) -0.20132(8) 0.13850(18) 0.0172(3) Uani 1 1 d . . . H3A H 0.2910 -0.2557 0.0814 0.021 Uiso 1 1 calc R . . H3B H 0.3752 -0.2051 0.2691 0.021 Uiso 1 1 calc R . . C4 C 0.36024(15) -0.14311(8) 0.02923(18) 0.0190(3) Uani 1 1 d . . . H4A H 0.4315 -0.1722 -0.0141 0.023 Uiso 1 1 calc R . . H4B H 0.2751 -0.1241 -0.0832 0.023 Uiso 1 1 calc R . . C5 C 0.58432(14) -0.08386(8) 0.26308(17) 0.0146(3) Uani 1 1 d . . . C6 C 0.36205(14) -0.00124(8) 0.13303(17) 0.0147(3) Uani 1 1 d . . . H6 H 0.2601 0.0027 0.0483 0.018 Uiso 1 1 calc R . . C7 C 0.42575(14) 0.06358(8) 0.23877(17) 0.0139(3) Uani 1 1 d . . . C8 C 0.34433(15) 0.14175(8) 0.2291(2) 0.0211(3) Uani 1 1 d . . . H8A H 0.3872 0.1834 0.1734 0.032 Uiso 1 1 calc R . . H8B H 0.3553 0.1583 0.3559 0.032 Uiso 1 1 calc R . . H8C H 0.2373 0.1347 0.1516 0.032 Uiso 1 1 calc R . . C9 C 0.57980(14) 0.05668(7) 0.37134(17) 0.0128(3) Uani 1 1 d . . . C10 C 0.80711(13) -0.02653(8) 0.50817(17) 0.0153(3) Uani 1 1 d . . . H10A H 0.8283 -0.0844 0.5392 0.018 Uiso 1 1 calc R . . H10B H 0.8197 0.0025 0.6256 0.018 Uiso 1 1 calc R . . C11 C 0.91965(13) 0.00616(8) 0.42972(17) 0.0160(3) Uani 1 1 d . . . H11A H 0.9010 0.0645 0.4020 0.019 Uiso 1 1 calc R . . H11B H 0.9064 -0.0220 0.3110 0.019 Uiso 1 1 calc R . . O4 O 0.64847(11) 0.11115(6) 0.47767(13) 0.0193(2) Uani 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 0.0158(5) 0.0264(5) 0.0251(5) 0.0071(4) 0.0050(4) -0.0037(4) N1 0.0114(5) 0.0164(5) 0.0144(5) -0.0017(4) 0.0037(4) -0.0034(4) C1 0.0180(8) 0.0486(10) 0.0376(9) 0.0165(8) 0.0126(6) -0.0001(7) O2 0.0176(5) 0.0236(5) 0.0362(6) 0.0082(4) 0.0075(4) 0.0023(4) N2 0.0073(5) 0.0140(5) 0.0165(5) 0.0008(4) 0.0031(4) -0.0016(4) C2 0.0147(6) 0.0183(6) 0.0153(6) -0.0007(5) 0.0009(5) -0.0046(5) O3 0.0172(5) 0.0175(5) 0.0340(6) -0.0041(4) 0.0091(4) 0.0022(4) C3 0.0159(6) 0.0146(6) 0.0185(6) -0.0030(5) 0.0035(5) -0.0032(5) C4 0.0185(7) 0.0216(7) 0.0160(6) -0.0059(5) 0.0055(5) -0.0068(5) C5 0.0111(6) 0.0164(6) 0.0173(6) -0.0004(5) 0.0065(5) -0.0024(4) C6 0.0104(6) 0.0201(6) 0.0132(6) 0.0044(5) 0.0039(4) -0.0009(5) C7 0.0116(6) 0.0154(6) 0.0156(6) 0.0048(4) 0.0060(5) 0.0000(4) C8 0.0176(7) 0.0174(6) 0.0282(7) 0.0065(5) 0.0087(5) 0.0039(5) C9 0.0118(6) 0.0138(6) 0.0140(6) 0.0027(4) 0.0061(4) -0.0022(4) C10 0.0068(6) 0.0199(6) 0.0167(6) 0.0042(5) 0.0018(4) -0.0014(4) C11 0.0079(6) 0.0213(6) 0.0169(6) 0.0034(5) 0.0024(5) -0.0020(5) O4 0.0188(5) 0.0152(5) 0.0210(5) -0.0019(4) 0.0040(4) -0.0047(3) _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 C2 1.3429(17) . ? O1 C1 1.4453(19) . ? N1 C6 1.3727(17) . ? N1 C5 1.3806(17) . ? N1 C4 1.4710(16) . ? O2 C2 1.2044(17) . ? N2 C5 1.3923(16) . ? N2 C9 1.3992(16) . ? N2 C10 1.4688(16) . ? C2 C3 1.5008(19) . ? O3 C5 1.2172(17) . ? C3 C4 1.5223(18) . ? C6 C7 1.3456(19) . ? C7 C9 1.4480(18) . ? C7 C8 1.4979(18) . ? C9 O4 1.2283(16) . ? C10 C11 1.5196(17) . ? C11 C11 1.525(2) 3_756 ? 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 O1 C1 116.00(12) . . ? C6 N1 C5 122.00(11) . . ? C6 N1 C4 121.19(11) . . ? C5 N1 C4 116.70(11) . . ? C5 N2 C9 125.02(11) . . ? C5 N2 C10 117.38(11) . . ? C9 N2 C10 117.59(10) . . ? O2 C2 O1 123.25(13) . . ? O2 C2 C3 126.26(13) . . ? O1 C2 C3 110.46(11) . . ? C2 C3 C4 113.32(11) . . ? N1 C4 C3 112.65(11) . . ? O3 C5 N1 122.42(12) . . ? O3 C5 N2 122.34(12) . . ? N1 C5 N2 115.24(11) . . ? C7 C6 N1 123.27(12) . . ? C6 C7 C9 118.19(12) . . ? C6 C7 C8 123.33(12) . . ? C9 C7 C8 118.46(11) . . ? O4 C9 N2 119.77(11) . . ? O4 C9 C7 123.99(12) . . ? N2 C9 C7 116.25(11) . . ? N2 C10 C11 112.10(10) . . ? C10 C11 C11 110.42(13) . 3_756 ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.413 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.049 data_Compound2 _database_code_depnum_ccdc_archive 'CCDC 841956' #TrackingRef 'Compound2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Hexyl-linked bis-thymine propanoate ; _chemical_name_common 'Hexyl-linked bis-thymine propanoate' _chemical_melting_point ? _chemical_formula_moiety 'C24 H34 N4 O8, H2 O' _chemical_formula_sum 'C24 H36 N4 O9' _chemical_formula_weight 524.57 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.4706(5) _cell_length_b 9.3600(19) _cell_length_c 16.0501(3) _cell_angle_alpha 90.00 _cell_angle_beta 131.959(3) _cell_angle_gamma 90.00 _cell_volume 2510.3(5) _cell_formula_units_Z 4 _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 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9979 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.710699 _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 15754 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2179 _reflns_number_gt 1961 _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^)+(0.0614P)^2^+3.5841P] 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 2179 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.53358(8) 0.33511(15) 0.64011(11) 0.0257(3) Uani 1 1 d . . . O2 O 0.35979(8) 0.00711(14) 0.36849(11) 0.0251(3) Uani 1 1 d . . . O3 O 0.78269(7) 0.18225(14) 0.70111(11) 0.0255(3) Uani 1 1 d . . . N4 N 0.44466(8) 0.17344(16) 0.50296(12) 0.0185(3) Uani 1 1 d . . . O5 O 0.67938(8) 0.21371(16) 0.51645(11) 0.0299(4) Uani 1 1 d . . . N6 N 0.53363(8) 0.29770(16) 0.50037(12) 0.0185(3) Uani 1 1 d . . . C7 C 0.50215(10) 0.22909(19) 0.40231(14) 0.0197(4) Uani 1 1 d . . . H7 H 0.5223 0.2524 0.3676 0.024 Uiso 1 1 calc R . . C8 C 0.41220(10) 0.09635(19) 0.40550(14) 0.0188(4) Uani 1 1 d . . . C9 C 0.40775(10) 0.1507(2) 0.55096(14) 0.0212(4) Uani 1 1 d . . . H9A H 0.4468 0.1757 0.6315 0.025 Uiso 1 1 calc R . . H9B H 0.3938 0.0485 0.5444 0.025 Uiso 1 1 calc R . . C11 C 0.50589(10) 0.27232(19) 0.55370(14) 0.0191(4) Uani 1 1 d . . . C12 C 0.44411(10) 0.13070(19) 0.35409(14) 0.0195(4) Uani 1 1 d . . . C13 C 0.59968(10) 0.4004(2) 0.55231(15) 0.0240(4) Uani 1 1 d . . . H13A H 0.5896 0.4840 0.5792 0.029 Uiso 1 1 calc R . . H13B H 0.6007 0.4345 0.4949 0.029 Uiso 1 1 calc R . . C14 C 0.40812(11) 0.0567(2) 0.24657(15) 0.0264(4) Uani 1 1 d . . . H14A H 0.4330 0.0927 0.2187 0.040 Uiso 1 1 calc R . . H14B H 0.3504 0.0754 0.1909 0.040 Uiso 1 1 calc R . . H14C H 0.4174 -0.0464 0.2598 0.040 Uiso 1 1 calc R . . C15 C 0.29078(10) 0.2134(2) 0.53531(15) 0.0213(4) Uani 1 1 d . . . H15A H 0.2837 0.1092 0.5360 0.026 Uiso 1 1 calc R . . H15B H 0.3253 0.2483 0.6134 0.026 Uiso 1 1 calc R . . C16 C 0.68075(11) 0.3371(2) 0.64974(15) 0.0249(4) Uani 1 1 d . . . H16A H 0.7196 0.4156 0.6945 0.030 Uiso 1 1 calc R . . H16B H 0.6763 0.2839 0.6987 0.030 Uiso 1 1 calc R . . C17 C 0.71184(11) 0.2384(2) 0.61260(15) 0.0225(4) Uani 1 1 d . . . C18 C 0.81816(12) 0.0878(2) 0.67290(17) 0.0305(5) Uani 1 1 d . . . H18A H 0.8233 0.1383 0.6245 0.046 Uiso 1 1 calc R . . H18B H 0.7839 0.0037 0.6334 0.046 Uiso 1 1 calc R . . H18C H 0.8712 0.0574 0.7417 0.046 Uiso 1 1 calc R . . C19 C 0.33243(11) 0.2414(2) 0.49103(15) 0.0221(4) Uani 1 1 d . . . H19A H 0.2948 0.2202 0.4098 0.027 Uiso 1 1 calc R . . H19B H 0.3470 0.3437 0.5011 0.027 Uiso 1 1 calc R . . O4 O 0.5000 0.5083(3) 0.7500 0.0459(6) Uani 1 2 d S . . H1 H 0.4940(18) 0.451(3) 0.788(2) 0.063(9) 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 0.0238(7) 0.0315(7) 0.0232(7) -0.0083(6) 0.0163(6) -0.0044(6) O2 0.0216(7) 0.0262(7) 0.0256(7) -0.0018(5) 0.0150(6) -0.0052(5) O3 0.0199(7) 0.0281(7) 0.0248(7) -0.0005(5) 0.0134(6) 0.0009(5) N4 0.0162(7) 0.0223(8) 0.0191(7) 0.0021(6) 0.0126(6) 0.0008(6) O5 0.0255(7) 0.0390(8) 0.0266(8) 0.0015(6) 0.0180(6) 0.0018(6) N6 0.0154(7) 0.0199(8) 0.0210(7) -0.0010(6) 0.0125(6) -0.0006(6) C7 0.0186(9) 0.0238(9) 0.0195(9) 0.0024(7) 0.0138(8) 0.0031(7) C8 0.0149(8) 0.0199(9) 0.0183(8) 0.0027(7) 0.0098(7) 0.0034(7) C9 0.0181(9) 0.0289(10) 0.0204(9) 0.0021(7) 0.0144(8) 0.0007(7) C11 0.0167(9) 0.0208(9) 0.0191(9) 0.0009(7) 0.0117(7) 0.0035(7) C12 0.0169(8) 0.0223(9) 0.0181(8) 0.0017(7) 0.0113(7) 0.0040(7) C13 0.0219(9) 0.0221(9) 0.0279(10) -0.0031(8) 0.0166(8) -0.0039(7) C14 0.0224(9) 0.0341(11) 0.0221(9) -0.0049(8) 0.0147(8) -0.0004(8) C15 0.0203(9) 0.0249(9) 0.0217(9) 0.0022(7) 0.0153(8) 0.0025(7) C16 0.0184(9) 0.0288(10) 0.0243(9) -0.0028(8) 0.0129(8) -0.0035(7) C17 0.0184(9) 0.0245(9) 0.0229(9) 0.0002(7) 0.0132(8) -0.0036(7) C18 0.0273(10) 0.0305(11) 0.0317(10) 0.0011(8) 0.0188(9) 0.0048(8) C19 0.0208(9) 0.0240(9) 0.0253(9) 0.0029(7) 0.0170(8) 0.0013(7) O4 0.0749(18) 0.0337(12) 0.0692(17) 0.000 0.0648(16) 0.000 _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 C11 1.226(2) . ? O2 C8 1.226(2) . ? O3 C17 1.343(2) . ? O3 C18 1.451(2) . ? N4 C11 1.384(2) . ? N4 C8 1.405(2) . ? N4 C9 1.477(2) . ? O5 C17 1.209(2) . ? N6 C11 1.375(2) . ? N6 C7 1.379(2) . ? N6 C13 1.472(2) . ? C7 C12 1.341(3) . ? C8 C12 1.445(2) . ? C9 C19 1.528(3) . ? C12 C14 1.499(2) . ? C13 C16 1.519(3) . ? C15 C15 1.528(3) 7_556 ? C15 C19 1.530(2) . ? C16 C17 1.501(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 C17 O3 C18 114.73(14) . . ? C11 N4 C8 124.79(14) . . ? C11 N4 C9 118.27(14) . . ? C8 N4 C9 116.88(14) . . ? C11 N6 C7 122.00(15) . . ? C11 N6 C13 117.72(15) . . ? C7 N6 C13 120.27(15) . . ? C12 C7 N6 122.51(16) . . ? O2 C8 N4 120.33(16) . . ? O2 C8 C12 123.89(16) . . ? N4 C8 C12 115.78(15) . . ? N4 C9 C19 111.31(14) . . ? O1 C11 N6 121.53(16) . . ? O1 C11 N4 122.66(16) . . ? N6 C11 N4 115.80(15) . . ? C7 C12 C8 119.04(16) . . ? C7 C12 C14 123.36(16) . . ? C8 C12 C14 117.57(16) . . ? N6 C13 C16 112.90(15) . . ? C15 C15 C19 112.43(18) 7_556 . ? C17 C16 C13 112.81(16) . . ? O5 C17 O3 123.52(18) . . ? O5 C17 C16 125.49(17) . . ? O3 C17 C16 110.97(15) . . ? C9 C19 C15 112.13(14) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.298 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.051 data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 841957' #TrackingRef 'Compound3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Butyl-linked bis-thymine propamide ; _chemical_name_common 'Butyl-linked bis-thymine propamide' _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 N6 O6, H2 O' _chemical_formula_sum 'C20 H30 N6 O7' _chemical_formula_weight 466.50 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 tetragonal _symmetry_space_group_name_H-M P42/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x+1/2, z+1/2' '-x+1/2, -y+1/2, z' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'y, -x-1/2, -z-1/2' 'x-1/2, y-1/2, -z' '-y-1/2, x, -z-1/2' _cell_length_a 22.260(3) _cell_length_b 22.260(3) _cell_length_c 4.7700(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2363.6(7) _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 0.025 _exptl_crystal_size_mid 0.005 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9980 _exptl_absorpt_correction_T_max 0.9990 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.710702 _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 28507 _diffrn_reflns_av_R_equivalents 0.1751 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2084 _reflns_number_gt 1532 _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^)+(0.0864P)^2^+1.1368P] 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 2084 _refine_ls_number_parameters 171 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1452 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.076 _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 0.63200(8) 0.39808(8) -0.3428(4) 0.0238(5) Uani 1 1 d . . . O2 O 0.49535(8) 0.35009(9) 0.3335(4) 0.0272(5) Uani 1 1 d . . . N3 N 0.53384(9) 0.27495(10) 0.0646(5) 0.0209(5) Uani 1 1 d . . . N4 N 0.56419(9) 0.37434(9) -0.0016(4) 0.0172(5) Uani 1 1 d . . . C5 C 0.60372(11) 0.35904(11) -0.2177(5) 0.0172(6) Uani 1 1 d . . . C6 C 0.57436(12) 0.25722(12) -0.1364(6) 0.0205(6) Uani 1 1 d . . . H6 H 0.5775 0.2156 -0.1780 0.025 Uiso 1 1 calc R . . C7 C 0.55822(12) 0.43833(11) 0.0790(6) 0.0218(6) Uani 1 1 d . . . H7A H 0.5944 0.4605 0.0170 0.026 Uiso 1 1 calc R . . H7B H 0.5559 0.4413 0.2858 0.026 Uiso 1 1 calc R . . C8 C 0.52877(11) 0.33412(12) 0.1442(6) 0.0194(6) Uani 1 1 d . . . C9 C 0.65442(12) 0.27589(12) -0.4908(6) 0.0223(6) Uani 1 1 d . . . H9A H 0.6951 0.2825 -0.4186 0.033 Uiso 1 1 calc R . . H9B H 0.6488 0.2992 -0.6629 0.033 Uiso 1 1 calc R . . H9C H 0.6488 0.2331 -0.5314 0.033 Uiso 1 1 calc R . . C10 C 0.50298(12) 0.46738(11) -0.0485(6) 0.0213(6) Uani 1 1 d . . . H10A H 0.4667 0.4446 0.0076 0.026 Uiso 1 1 calc R . . H10B H 0.5060 0.4662 -0.2555 0.026 Uiso 1 1 calc R . . C11 C 0.49568(12) 0.23000(12) 0.2028(6) 0.0254(7) Uani 1 1 d . . . H11A H 0.4855 0.2442 0.3936 0.031 Uiso 1 1 calc R . . H11B H 0.5185 0.1920 0.2220 0.031 Uiso 1 1 calc R . . C12 C 0.60952(11) 0.29548(11) -0.2761(5) 0.0173(6) Uani 1 1 d . . . C13 C 0.43839(16) 0.21785(15) 0.0437(7) 0.0387(8) Uani 1 1 d . . . H13A H 0.4475 0.2113 -0.1572 0.046 Uiso 1 1 calc R . . H13B H 0.4111 0.2528 0.0593 0.046 Uiso 1 1 calc R . . O14 O 0.40824(14) 0.15438(12) 0.4199(5) 0.0661(9) Uani 1 1 d U . . N15 N 0.38489(13) 0.12417(13) -0.0149(6) 0.0385(7) Uani 1 1 d . . . C16 C 0.40846(16) 0.16239(15) 0.1655(7) 0.0401(8) Uani 1 1 d . . . H1 H 0.3887(15) 0.1295(16) -0.196(8) 0.041(10) Uiso 1 1 d . . . H4 H 0.3740(19) 0.089(2) 0.061(9) 0.071(14) Uiso 1 1 d . . . O3 O 0.2570(15) 0.2384(8) 0.481(5) 0.34(2) Uani 0.50 1 d PDU A -1 H1W H 0.275(4) 0.205(3) 0.421(16) 0.09(3) Uiso 0.50 1 d PD B -1 H4W H 0.260(5) 0.237(5) 0.666(5) 0.04(3) Uiso 0.50 1 d PD C -1 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 0.0220(10) 0.0197(10) 0.0297(11) 0.0017(8) 0.0052(8) -0.0054(8) O2 0.0239(10) 0.0308(11) 0.0270(11) 0.0029(9) 0.0066(9) 0.0084(8) N3 0.0162(11) 0.0191(11) 0.0276(13) 0.0059(10) 0.0041(9) 0.0014(9) N4 0.0185(11) 0.0139(11) 0.0191(12) -0.0013(9) 0.0012(9) 0.0021(8) C5 0.0130(12) 0.0200(13) 0.0186(14) 0.0008(11) -0.0036(10) -0.0016(10) C6 0.0201(13) 0.0164(13) 0.0250(14) 0.0008(11) -0.0009(11) 0.0038(10) C7 0.0253(14) 0.0164(13) 0.0236(14) -0.0040(11) -0.0009(12) 0.0014(11) C8 0.0165(13) 0.0203(14) 0.0215(14) 0.0033(11) -0.0012(12) 0.0056(10) C9 0.0194(13) 0.0221(14) 0.0254(15) -0.0019(12) 0.0004(11) 0.0006(11) C10 0.0265(14) 0.0165(14) 0.0210(13) -0.0015(11) 0.0013(12) 0.0030(11) C11 0.0225(14) 0.0209(14) 0.0329(17) 0.0112(12) 0.0070(12) 0.0034(11) C12 0.0148(12) 0.0177(13) 0.0194(13) -0.0003(11) -0.0036(11) 0.0020(10) C13 0.052(2) 0.0365(18) 0.0275(17) 0.0055(14) -0.0048(15) -0.0261(16) O14 0.113(2) 0.0640(18) 0.0219(12) 0.0069(12) 0.0012(14) -0.0602(17) N15 0.0567(19) 0.0355(16) 0.0234(15) 0.0048(13) 0.0011(13) -0.0278(14) C16 0.052(2) 0.0422(19) 0.0261(17) 0.0068(15) 0.0030(15) -0.0261(16) O3 0.18(2) 0.070(17) 0.77(6) -0.02(3) 0.03(5) 0.066(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.228(3) . ? O2 C8 1.222(3) . ? N3 C6 1.374(3) . ? N3 C8 1.375(3) . ? N3 C11 1.469(3) . ? N4 C8 1.381(3) . ? N4 C5 1.397(3) . ? N4 C7 1.481(3) . ? C5 C12 1.448(4) . ? C6 C12 1.335(4) . ? C7 C10 1.517(4) . ? C9 C12 1.496(4) . ? C10 C10 1.530(5) 5_665 ? C11 C13 1.508(4) . ? C13 C16 1.518(4) . ? O14 C16 1.226(4) . ? N15 C16 1.319(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N3 C8 121.5(2) . . ? C6 N3 C11 119.8(2) . . ? C8 N3 C11 118.7(2) . . ? C8 N4 C5 125.0(2) . . ? C8 N4 C7 116.2(2) . . ? C5 N4 C7 118.8(2) . . ? O1 C5 N4 120.6(2) . . ? O1 C5 C12 123.5(2) . . ? N4 C5 C12 115.9(2) . . ? C12 C6 N3 123.3(2) . . ? N4 C7 C10 112.3(2) . . ? O2 C8 N3 122.2(2) . . ? O2 C8 N4 122.1(2) . . ? N3 C8 N4 115.8(2) . . ? C7 C10 C10 110.7(3) . 5_665 ? N3 C11 C13 112.7(2) . . ? C6 C12 C5 118.4(2) . . ? C6 C12 C9 123.2(2) . . ? C5 C12 C9 118.4(2) . . ? C11 C13 C16 108.9(3) . . ? O14 C16 N15 123.4(3) . . ? O14 C16 C13 119.9(3) . . ? N15 C16 C13 116.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.322 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.063