# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'CIFs.cif' _publ_contact_author_name 'Thomas Gelbrich' _publ_contact_author_address ; Institut f\"ur Pharmazie, Universit\"at Innsbruck, Innrain 52, 6020 Innsbruck, Austria ; _publ_contact_author_email thomas.gelbrich@uibk.ac.at loop_ _publ_author_name 'D. Rossi' 'T. Gelbrich' 'V. Kahlenberg' 'U. J. Griesser' #===================================================== #==================================================== data_Nbtl-I _database_code_depnum_ccdc_archive 'CCDC 848445' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-ethyl,5-(1-methylbutyl)barbituric acid ; _chemical_name_common 'pentobarbital, nembutal' _chemical_melting_point ? _chemical_formula_moiety 'C11 H18 N2 O3' _chemical_formula_sum 'C11 H18 N2 O3' _chemical_formula_weight 226.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.7361(6) _cell_length_b 11.1568(9) _cell_length_c 10.1886(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.205(6) _cell_angle_gamma 90.00 _cell_volume 1251.97(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2641 _cell_measurement_theta_min 3.9613 _cell_measurement_theta_max 67.1325 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas colourless _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_T_min 0.61046 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.3575 _diffrn_reflns_number 6203 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.64 _diffrn_reflns_theta_max 66.50 _reflns_number_total 2098 _reflns_number_gt 1330 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. a) Distance restraints were applied to obtain sensible values for all C(sp3)-C(sp3) bond distances of the 1-methylbutyl group: DFIX 1.52 .01 C5 C7 C7 C8 C5 C9 C9 C13 C9 C10 C10 C11 C11 C12 SADI .01 C5 C7 C7 C8 C5 C9 C9 C13 C9 C10 C10 C11 C11 C12 b) H atoms attached N were included in the refinement with isotropic U(iso) values and an N-H distance restraint of 0.88(2) %A was applied: DFIX 0.88 .02 N1 H1 N3 H3 ; _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^)+(0.0100P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2098 _refine_ls_number_parameters 162 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1233 _refine_ls_R_factor_gt 0.0880 _refine_ls_wR_factor_ref 0.1740 _refine_ls_wR_factor_gt 0.1612 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.4378(2) 0.1330(3) 0.5801(2) 0.0707(9) Uani 1 1 d . . . O4 O 0.6623(2) 0.1344(3) 0.3032(2) 0.0749(10) Uani 1 1 d . . . O6 O 0.8372(2) 0.2031(3) 0.7918(2) 0.0639(8) Uani 1 1 d . . . N1 N 0.6397(2) 0.1645(3) 0.6844(3) 0.0496(8) Uani 1 1 d D . . H1 H 0.641(4) 0.158(4) 0.7689(19) 0.080(14) Uiso 1 1 d D . . N3 N 0.5519(2) 0.1499(3) 0.4432(3) 0.0522(9) Uani 1 1 d D . . H3 H 0.4884(19) 0.151(3) 0.369(2) 0.049(10) Uiso 1 1 d D . . C2 C 0.5378(3) 0.1489(4) 0.5715(3) 0.0484(9) Uani 1 1 d . . . C4 C 0.6608(3) 0.1520(4) 0.4205(3) 0.0529(10) Uani 1 1 d . . . C5 C 0.7753(3) 0.1805(3) 0.5422(3) 0.0570(11) Uani 1 1 d D . . C6 C 0.7551(3) 0.1859(4) 0.6839(3) 0.0473(9) Uani 1 1 d . . . C7 C 0.8721(3) 0.0839(4) 0.5527(4) 0.0773(17) Uani 1 1 d D . . H7A H 0.8789 0.0735 0.4593 0.101(16) Uiso 1 1 calc R . . H7B H 0.9514 0.1133 0.6167 0.071(12) Uiso 1 1 calc R . . C8 C 0.8473(4) -0.0382(4) 0.6045(5) 0.0774(15) Uani 1 1 d D . . H8A H 0.8493 -0.0310 0.7011 0.077(13) Uiso 1 1 calc R . . H8B H 0.9095 -0.0953 0.6007 0.12(2) Uiso 1 1 calc R . . H8C H 0.7671 -0.0668 0.5449 0.112(18) Uiso 1 1 calc R . . C9 C 0.8238(4) 0.3031(4) 0.5188(5) 0.0800(14) Uani 1 1 d D . . H9 H 0.8916 0.3217 0.6078 0.116(19) Uiso 1 1 calc R . . C10 C 0.8805(5) 0.3060(6) 0.4048(6) 0.1003(18) Uani 1 1 d D . . H10A H 0.8167 0.2978 0.3130 0.150 Uiso 1 1 calc R . . H10B H 0.9384 0.2398 0.4190 0.150 Uiso 1 1 calc R . . H10C H 0.9230 0.3823 0.4091 0.150 Uiso 1 1 calc R . . C11 C 0.7299(5) 0.3990(4) 0.5047(6) 0.0987(18) Uani 1 1 d D . . H11A H 0.6945 0.3874 0.5790 0.118 Uiso 1 1 calc R . . H11B H 0.6637 0.3892 0.4135 0.118 Uiso 1 1 calc R . . C12 C 0.7788(8) 0.5260(6) 0.5145(9) 0.148(3) Uani 1 1 d D . . H12A H 0.8100 0.5418 0.4374 0.178 Uiso 1 1 calc R . . H12B H 0.8457 0.5382 0.6046 0.178 Uiso 1 1 calc R . . C13 C 0.6730(9) 0.6091(9) 0.5036(11) 0.215(5) Uani 1 1 d D . . H13A H 0.6089 0.5981 0.4125 0.323 Uiso 1 1 calc R . . H13B H 0.7010 0.6925 0.5130 0.323 Uiso 1 1 calc R . . H13C H 0.6411 0.5902 0.5783 0.323 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0313(12) 0.144(3) 0.0401(13) -0.0066(15) 0.0168(11) -0.0105(15) O4 0.0318(12) 0.162(3) 0.0302(12) 0.0010(15) 0.0100(10) -0.0028(15) O6 0.0362(13) 0.115(2) 0.0341(12) -0.0059(14) 0.0040(10) -0.0084(14) N1 0.0320(13) 0.090(3) 0.0268(13) 0.0020(14) 0.0105(11) -0.0011(14) N3 0.0261(13) 0.103(3) 0.0274(13) 0.0000(15) 0.0088(11) -0.0031(15) C2 0.0288(16) 0.084(3) 0.0311(15) -0.0016(17) 0.0086(13) -0.0040(17) C4 0.0296(16) 0.096(3) 0.0318(16) 0.0050(18) 0.0096(13) -0.0067(18) C5 0.0302(16) 0.106(4) 0.0337(17) 0.0043(19) 0.0095(14) -0.0122(19) C6 0.0316(16) 0.077(3) 0.0299(16) 0.0016(16) 0.0067(13) -0.0057(17) C7 0.0236(16) 0.177(6) 0.0313(18) -0.006(2) 0.0099(14) 0.010(2) C8 0.038(2) 0.114(4) 0.073(3) -0.021(3) 0.010(2) 0.003(2) C9 0.072(3) 0.100(4) 0.065(3) 0.003(3) 0.020(2) -0.022(3) C11 0.113(5) 0.088(4) 0.093(4) 0.006(3) 0.033(3) -0.031(4) C12 0.154(7) 0.120(7) 0.169(8) 0.014(5) 0.054(6) -0.013(6) C13 0.186(10) 0.183(10) 0.228(11) 0.084(9) 0.008(9) 0.054(9) C10 0.097(4) 0.120(5) 0.097(4) 0.016(3) 0.050(3) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.219(4) . ? O4 C4 1.217(4) . ? O6 C6 1.201(4) . ? N1 C2 1.354(4) . ? N1 C6 1.377(4) . ? N1 H1 0.859(10) . ? N3 C2 1.373(4) . ? N3 C4 1.375(4) . ? N3 H3 0.859(10) . ? C4 C5 1.514(4) . ? C5 C9 1.532(4) . ? C5 C7 1.542(4) . ? C5 C6 1.543(4) . ? C7 C8 1.525(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.508(5) . ? C9 C10 1.525(4) . ? C9 H9 1.0000 . ? C11 C12 1.519(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 N1 C6 126.9(3) . . ? C2 N1 H1 123(3) . . ? C6 N1 H1 110(3) . . ? C2 N3 C4 125.8(3) . . ? C2 N3 H3 119(2) . . ? C4 N3 H3 115(2) . . ? O2 C2 N1 123.2(3) . . ? O2 C2 N3 120.4(3) . . ? N1 C2 N3 116.4(3) . . ? O4 C4 N3 119.5(3) . . ? O4 C4 C5 121.8(3) . . ? N3 C4 C5 118.6(3) . . ? C4 C5 C9 109.4(3) . . ? C4 C5 C7 109.5(3) . . ? C9 C5 C7 109.3(3) . . ? C4 C5 C6 113.3(2) . . ? C9 C5 C6 107.2(3) . . ? C7 C5 C6 108.0(3) . . ? O6 C6 N1 120.2(3) . . ? O6 C6 C5 122.0(3) . . ? N1 C6 C5 117.8(3) . . ? C8 C7 C5 115.1(3) . . ? C8 C7 H7A 108.5 . . ? C5 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C5 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 114.2(4) . . ? C11 C9 C5 110.5(3) . . ? C10 C9 C5 114.9(4) . . ? C11 C9 H9 105.4 . . ? C10 C9 H9 105.4 . . ? C5 C9 H9 105.4 . . ? C9 C11 C12 114.1(5) . . ? C9 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C9 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 106.4(7) . . ? C11 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? C11 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.859(10) 2.07(2) 2.867(3) 154(4) 2_656 N3 H3 O4 0.859(10) 2.025(12) 2.880(3) 173(4) 2_655 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 66.50 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.424 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.050 #==================================================== #==================================================== data_Nbtl-III _database_code_depnum_ccdc_archive 'CCDC 848446' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-ethyl,5-(1-methylbutyl)barbituric acid ; _chemical_name_common 'pentobarbital, nembutal' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N2 O3' _chemical_formula_weight 226.27 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 orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 16.7545(15) _cell_length_b 9.8660(8) _cell_length_c 7.1799(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1186.84(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12496 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9926 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type ; Bruker-Nonius APEX II CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 6337 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1981 _reflns_number_gt 1603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H atoms attached N were included in the refinement with isotropic U(iso) values and an N-H distance restraint of 0.88(2) %A was applied: DFIX .88 .02 N1 H1 N3 H3 ; _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^)+(0.0291P)^2^+0.9131P] 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_number_reflns 1981 _refine_ls_number_parameters 169 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1149 _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 0.23119(17) 0.8780(3) 0.5322(5) 0.0242(6) Uani 1 1 d D . . H1 H 0.2037(19) 0.939(3) 0.601(5) 0.028(10) Uiso 1 1 d D . . O2 O 0.11557(13) 0.7906(3) 0.4235(4) 0.0292(6) Uani 1 1 d . . . N3 N 0.23122(18) 0.6936(3) 0.3280(4) 0.0240(7) Uani 1 1 d D . . H3 H 0.2035(18) 0.633(3) 0.271(4) 0.014(9) Uiso 1 1 d D . . O4 O 0.34485(14) 0.5964(2) 0.2277(4) 0.0307(6) Uani 1 1 d . . . O6 O 0.34488(14) 0.9783(2) 0.6290(3) 0.0272(6) Uani 1 1 d . . . C2 C 0.18727(19) 0.7883(3) 0.4292(5) 0.0228(7) Uani 1 1 d . . . C4 C 0.3125(2) 0.6826(3) 0.3255(5) 0.0233(8) Uani 1 1 d . . . C5 C 0.36233(19) 0.7771(3) 0.4457(5) 0.0239(7) Uani 1 1 d . . . C6 C 0.31335(19) 0.8864(3) 0.5422(5) 0.0227(8) Uani 1 1 d . . . C7 C 0.4242(2) 0.8489(4) 0.3161(5) 0.0273(8) Uani 1 1 d . . . H7A H 0.4573 0.9112 0.3916 0.022(9) Uiso 1 1 calc R . . H7B H 0.4600 0.7798 0.2613 0.022(9) Uiso 1 1 calc R . . C8 C 0.3847(2) 0.9284(4) 0.1600(5) 0.0347(9) Uani 1 1 d . . . H8A H 0.4259 0.9693 0.0810 0.036(11) Uiso 1 1 calc R . . H8B H 0.3512 1.0000 0.2133 0.038(11) Uiso 1 1 calc R . . H8C H 0.3516 0.8673 0.0850 0.049(13) Uiso 1 1 calc R . . C9 C 0.4034(2) 0.6841(4) 0.5962(5) 0.0276(8) Uani 1 1 d . . . H9 H 0.4310 0.6103 0.5258 0.021(8) Uiso 1 1 calc R . . C10 C 0.3408(2) 0.6145(4) 0.7176(6) 0.0343(9) Uani 1 1 d . . . H10A H 0.3012 0.5700 0.6379 0.052 Uiso 1 1 calc R . . H10B H 0.3142 0.6821 0.7960 0.052 Uiso 1 1 calc R . . H10C H 0.3667 0.5467 0.7968 0.052 Uiso 1 1 calc R . . C11 C 0.4674(2) 0.7538(4) 0.7121(5) 0.0298(8) Uani 1 1 d . . . H11A H 0.4421 0.8252 0.7890 0.025(9) Uiso 1 1 calc R . . H11B H 0.5059 0.7984 0.6274 0.037(10) Uiso 1 1 calc R . . C12 C 0.5128(2) 0.6557(4) 0.8405(6) 0.0347(9) Uani 1 1 d . . . H12A H 0.4765 0.6235 0.9399 0.039(11) Uiso 1 1 calc R . . H12B H 0.5303 0.5759 0.7675 0.076(17) Uiso 1 1 calc R . . C13 C 0.5850(2) 0.7224(4) 0.9284(6) 0.0398(9) Uani 1 1 d . . . H13A H 0.6118 0.6575 1.0107 0.061(14) Uiso 1 1 calc R . . H13B H 0.5679 0.8014 1.0010 0.089(19) Uiso 1 1 calc R . . H13C H 0.6220 0.7514 0.8306 0.035(10) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0244(15) 0.0226(16) 0.0255(15) -0.0089(13) 0.0020(13) 0.0002(12) O2 0.0235(14) 0.0293(13) 0.0347(13) -0.0060(11) 0.0001(12) -0.0034(11) N3 0.0233(16) 0.0197(15) 0.0290(16) -0.0081(14) -0.0036(13) -0.0014(12) O4 0.0280(14) 0.0266(13) 0.0374(14) -0.0114(12) -0.0018(13) 0.0011(11) O6 0.0258(12) 0.0201(12) 0.0357(14) -0.0115(11) -0.0007(12) -0.0021(10) C2 0.0265(19) 0.0193(16) 0.0226(17) 0.0012(13) 0.0017(17) -0.0012(16) C4 0.029(2) 0.0168(17) 0.0243(18) -0.0008(16) -0.0016(17) 0.0017(14) C5 0.0243(17) 0.0170(15) 0.0305(19) -0.0057(14) -0.0009(17) -0.0003(15) C6 0.0259(18) 0.0206(18) 0.0215(18) -0.0002(15) 0.0062(15) -0.0017(15) C7 0.0258(19) 0.0265(18) 0.030(2) -0.0050(16) 0.0014(17) -0.0018(15) C8 0.036(2) 0.034(2) 0.034(2) -0.0008(17) 0.0034(18) -0.0062(18) C9 0.032(2) 0.0229(19) 0.028(2) 0.0029(14) -0.0003(16) 0.0014(16) C10 0.033(2) 0.031(2) 0.039(2) 0.0086(17) -0.0029(18) -0.0068(16) C11 0.035(2) 0.0254(18) 0.0291(19) -0.0023(16) 0.0010(17) 0.0016(15) C12 0.039(2) 0.034(2) 0.031(2) 0.0042(17) -0.0073(18) 0.0048(18) C13 0.038(2) 0.042(2) 0.040(2) 0.0068(19) -0.010(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.368(5) . ? N1 C6 1.381(4) . ? O2 C2 1.202(4) . ? N3 C4 1.366(4) . ? N3 C2 1.394(5) . ? O4 C4 1.229(4) . ? O6 C6 1.220(4) . ? C4 C5 1.521(5) . ? C5 C6 1.522(5) . ? C5 C7 1.563(5) . ? C5 C9 1.576(5) . ? C7 C8 1.520(5) . ? C9 C11 1.521(5) . ? C9 C10 1.527(5) . ? C11 C12 1.538(5) . ? C12 C13 1.515(5) . ? 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 N1 C6 127.1(3) . . ? C4 N3 C2 125.9(3) . . ? O2 C2 N1 122.9(3) . . ? O2 C2 N3 121.5(3) . . ? N1 C2 N3 115.5(3) . . ? O4 C4 N3 120.2(3) . . ? O4 C4 C5 120.4(3) . . ? N3 C4 C5 119.4(3) . . ? C4 C5 C6 113.4(3) . . ? C4 C5 C7 107.7(3) . . ? C6 C5 C7 107.9(3) . . ? C4 C5 C9 105.8(3) . . ? C6 C5 C9 109.6(3) . . ? C7 C5 C9 112.5(3) . . ? O6 C6 N1 120.2(3) . . ? O6 C6 C5 121.7(3) . . ? N1 C6 C5 118.1(3) . . ? C8 C7 C5 112.6(3) . . ? C11 C9 C10 112.1(3) . . ? C11 C9 C5 114.8(3) . . ? C10 C9 C5 110.7(3) . . ? C9 C11 C12 113.1(3) . . ? C13 C12 C11 111.8(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.901(18) 1.98(2) 2.870(4) 170(3) 4 N3 H3 O6 0.863(18) 2.004(19) 2.860(4) 171(3) 4_544 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.201 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.052 #==================================================== #==================================================== data_Nbtl-IV _database_code_depnum_ccdc_archive 'CCDC 848447' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-ethyl,5-(1-methylbutyl)barbituric acid ; _chemical_name_common 'pentobarbital, nembutal' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N2 O3' _chemical_formula_weight 226.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 14.5136(10) _cell_length_b 6.8344(3) _cell_length_c 12.4979(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.762(6) _cell_angle_gamma 90.00 _cell_volume 1198.77(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1627 _cell_measurement_theta_min 3.6607 _cell_measurement_theta_max 62.7308 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.754 _exptl_absorpt_correction_T_min 0.85416 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_reflns_number 4960 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 7.21 _diffrn_reflns_theta_max 62.69 _reflns_number_total 1839 _reflns_number_gt 1051 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The butyl chain of the 1-methylbutyl group is disordered over two positions: component 1 (fraction 0.59): C9-C10-C11-C12-C13 component 2 (fraction 0.41): C9-C10'-C11'-C12'-C13' --------------------------------------------------------------------------- a) Distance restraints were applied to obtain sensible values for all C(sp3)-C(sp3) bond distances of the disordered 1-methylbutyl groups: DFIX 1.52 .005 C9 C10 C9 C10' DFIX 1.52 .008 C5 C9 C9 C11 C11 C12 C12 C13 C9 C11' C11' C12' C12' C13' DFIX 1.52 .008 C5 C7 C7 C8 C5 C9 C9 C10 SADI .01 C9 C12 C11 C13 C9 C12' C11' C13' b) H atoms attached N were included in the refinement with isotropic U(iso) values and an N-H distance restraint of 0.88(2) %A was applied: DFIX .88 .02 H1 N1 H3 N3 ; _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^)+(0.0300P)^2^+0.7000P] 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_number_reflns 1839 _refine_ls_number_parameters 183 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.146 _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 O2 O 0.5135(2) 0.2246(3) 0.73147(19) 0.0528(7) Uani 1 1 d . . . O4 O 0.38297(19) 0.0449(3) 1.00731(17) 0.0472(7) Uani 1 1 d . . . O6 O 0.2127(2) 0.4302(4) 0.70459(19) 0.0552(7) Uani 1 1 d . . . N1 N 0.3609(2) 0.3203(4) 0.7186(2) 0.0429(8) Uani 1 1 d D . . H1 H 0.358(2) 0.372(5) 0.6518(19) 0.051 Uiso 1 1 d D . . N3 N 0.4457(2) 0.1407(4) 0.8697(2) 0.0449(8) Uani 1 1 d D . . H3 H 0.4996(18) 0.084(5) 0.910(3) 0.054 Uiso 1 1 d D . . C2 C 0.4450(3) 0.2285(5) 0.7696(3) 0.0397(9) Uani 1 1 d . . . C4 C 0.3727(3) 0.1310(4) 0.9181(3) 0.0386(9) Uani 1 1 d . . . C5 C 0.2783(3) 0.2294(4) 0.8630(2) 0.0401(9) Uani 1 1 d D A . C6 C 0.2811(3) 0.3367(5) 0.7569(3) 0.0407(9) Uani 1 1 d . . . C7 C 0.2590(3) 0.3840(5) 0.9454(3) 0.0482(10) Uani 1 1 d D . . H7A H 0.2003 0.4568 0.9095 0.058 Uiso 1 1 calc R . . H7B H 0.2475 0.3156 1.0106 0.058 Uiso 1 1 calc R . . C8 C 0.3401(3) 0.5298(5) 0.9846(3) 0.0607(12) Uani 1 1 d D . . H8A H 0.3972 0.4606 1.0261 0.073 Uiso 1 1 calc R . . H8B H 0.3216 0.6278 1.0324 0.073 Uiso 1 1 calc R . . H8C H 0.3537 0.5949 0.9204 0.073 Uiso 1 1 calc R . . C9 C 0.2012(3) 0.0687(5) 0.8308(3) 0.0679(13) Uani 1 1 d D . . H9 H 0.1450 0.1441 0.7874 0.081 Uiso 0.587(9) 1 calc PR A 1 H9' H 0.2175 -0.0158 0.8984 0.081 Uiso 0.413(9) 1 calc PR A 2 C10 C 0.2209(4) -0.0708(6) 0.7441(3) 0.0749(14) Uani 1 1 d D A . H10A H 0.1724 -0.1738 0.7287 0.112 Uiso 1 1 calc R . . H10B H 0.2840 -0.1299 0.7719 0.112 Uiso 1 1 calc R . . H10C H 0.2190 0.0017 0.6760 0.112 Uiso 1 1 calc R . . C11 C 0.1615(4) -0.0319(9) 0.9149(5) 0.050(2) Uani 0.587(9) 1 d PD A 1 H11A H 0.2087 -0.1297 0.9535 0.059 Uiso 0.587(9) 1 calc PR A 1 H11B H 0.1545 0.0663 0.9706 0.059 Uiso 0.587(9) 1 calc PR A 1 C12 C 0.0680(7) -0.133(2) 0.8737(9) 0.071(3) Uani 0.587(9) 1 d PD A 1 H12A H 0.0717 -0.2208 0.8119 0.085 Uiso 0.587(9) 1 calc PR A 1 H12B H 0.0182 -0.0342 0.8443 0.085 Uiso 0.587(9) 1 calc PR A 1 C13 C 0.0385(7) -0.2530(16) 0.9622(8) 0.083(3) Uani 0.587(9) 1 d PD A 1 H13A H 0.0866 -0.3538 0.9903 0.125 Uiso 0.587(9) 1 calc PR A 1 H13B H -0.0231 -0.3153 0.9301 0.125 Uiso 0.587(9) 1 calc PR A 1 H13C H 0.0332 -0.1669 1.0230 0.125 Uiso 0.587(9) 1 calc PR A 1 C11' C 0.1026(6) 0.1171(14) 0.8249(10) 0.077(4) Uani 0.413(9) 1 d PD A 2 H11C H 0.0791 0.2077 0.7621 0.093 Uiso 0.413(9) 1 calc PR A 2 H11D H 0.1002 0.1876 0.8934 0.093 Uiso 0.413(9) 1 calc PR A 2 C12' C 0.0353(7) -0.0573(19) 0.8110(15) 0.111(6) Uani 0.413(9) 1 d PD A 2 H12C H 0.0422 -0.1375 0.7475 0.133 Uiso 0.413(9) 1 calc PR A 2 H12D H -0.0313 -0.0101 0.7948 0.133 Uiso 0.413(9) 1 calc PR A 2 C13' C 0.0565(15) -0.183(3) 0.9151(18) 0.123(9) Uani 0.413(9) 1 d PD A 2 H13D H 0.1147 -0.2592 0.9198 0.184 Uiso 0.413(9) 1 calc PR A 2 H13E H 0.0031 -0.2724 0.9121 0.184 Uiso 0.413(9) 1 calc PR A 2 H13F H 0.0654 -0.0988 0.9803 0.184 Uiso 0.413(9) 1 calc PR A 2 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 O2 0.071(2) 0.0446(15) 0.0504(16) 0.0114(12) 0.0300(15) 0.0069(13) O4 0.087(2) 0.0292(12) 0.0316(12) 0.0048(10) 0.0268(12) 0.0091(12) O6 0.0674(19) 0.0532(16) 0.0444(15) 0.0100(13) 0.0132(14) 0.0079(15) N1 0.065(2) 0.0362(16) 0.0302(15) 0.0090(12) 0.0173(16) 0.0017(15) N3 0.070(2) 0.0375(16) 0.0332(16) 0.0106(13) 0.0242(16) 0.0144(15) C2 0.060(3) 0.0319(18) 0.0321(19) 0.0029(15) 0.0213(19) 0.0002(18) C4 0.068(3) 0.0243(16) 0.0285(17) 0.0018(14) 0.0210(18) 0.0044(16) C5 0.062(3) 0.0293(17) 0.0328(18) -0.0008(14) 0.0198(17) 0.0022(17) C6 0.059(3) 0.0314(19) 0.0327(19) -0.0021(15) 0.0143(19) -0.0020(18) C7 0.077(3) 0.0359(19) 0.0361(19) -0.0012(15) 0.0225(19) 0.0135(18) C8 0.109(4) 0.0281(19) 0.047(2) -0.0044(17) 0.024(2) 0.004(2) C9 0.100(4) 0.050(2) 0.067(3) -0.015(2) 0.044(3) -0.031(3) C10 0.112(4) 0.054(3) 0.070(3) -0.027(2) 0.044(3) -0.036(3) C11 0.066(6) 0.040(4) 0.047(4) 0.010(3) 0.023(3) -0.004(3) C12 0.051(7) 0.082(9) 0.084(8) 0.001(7) 0.026(6) -0.018(6) C13 0.091(8) 0.081(8) 0.087(7) 0.010(6) 0.037(6) -0.004(6) C11' 0.080(10) 0.071(8) 0.076(8) 0.010(6) 0.012(7) 0.005(7) C12' 0.098(13) 0.080(10) 0.148(17) 0.050(10) 0.022(11) 0.012(10) C13' 0.119(15) 0.082(16) 0.21(3) 0.038(15) 0.112(17) 0.016(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.207(4) . ? O4 C4 1.236(3) . ? O6 C6 1.221(4) . ? N1 C6 1.366(4) . ? N1 C2 1.376(5) . ? N1 H1 0.898(19) . ? N3 C4 1.349(4) . ? N3 C2 1.385(4) . ? N3 H3 0.906(19) . ? C4 C5 1.524(5) . ? C5 C6 1.524(4) . ? C5 C9 1.546(4) . ? C5 C7 1.550(4) . ? C7 C8 1.525(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11' 1.453(7) . ? C9 C11 1.489(5) . ? C9 C10 1.524(3) . ? C9 H9 1.0000 . ? C9 H9' 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.493(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.521(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C11' C12' 1.523(8) . ? C11' H11C 0.9900 . ? C11' H11D 0.9900 . ? C12' C13' 1.525(8) . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13' H13D 0.9800 . ? C13' H13E 0.9800 . ? C13' H13F 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 C6 N1 C2 127.4(3) . . ? C6 N1 H1 117(2) . . ? C2 N1 H1 116(2) . . ? C4 N3 C2 126.9(3) . . ? C4 N3 H3 113(2) . . ? C2 N3 H3 120(2) . . ? O2 C2 N1 123.4(3) . . ? O2 C2 N3 122.0(4) . . ? N1 C2 N3 114.6(3) . . ? O4 C4 N3 120.0(3) . . ? O4 C4 C5 120.4(3) . . ? N3 C4 C5 119.6(3) . . ? C6 C5 C4 112.7(3) . . ? C6 C5 C9 107.1(3) . . ? C4 C5 C9 108.2(3) . . ? C6 C5 C7 107.4(3) . . ? C4 C5 C7 107.1(3) . . ? C9 C5 C7 114.6(3) . . ? O6 C6 N1 120.1(3) . . ? O6 C6 C5 121.3(3) . . ? N1 C6 C5 118.6(3) . . ? C8 C7 C5 113.8(3) . . ? C8 C7 H7A 108.8 . . ? C5 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C5 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11' C9 C11 65.6(5) . . ? C11' C9 C10 117.9(6) . . ? C11 C9 C10 112.9(4) . . ? C11' C9 C5 119.3(5) . . ? C11 C9 C5 122.0(3) . . ? C10 C9 C5 112.0(3) . . ? C11' C9 H9 36.7 . . ? C11 C9 H9 102.2 . . ? C10 C9 H9 102.2 . . ? C5 C9 H9 102.2 . . ? C11' C9 H9' 101.1 . . ? C11 C9 H9' 35.8 . . ? C10 C9 H9' 101.1 . . ? C5 C9 H9' 101.1 . . ? H9 C9 H9' 137.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C9 116.9(6) . . ? C12 C11 H11A 108.1 . . ? C9 C11 H11A 108.1 . . ? C12 C11 H11B 108.1 . . ? C9 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C11 C12 C13 113.4(8) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C9 C11' C12' 115.0(7) . . ? C9 C11' H11C 108.5 . . ? C12' C11' H11C 108.5 . . ? C9 C11' H11D 108.5 . . ? C12' C11' H11D 108.5 . . ? H11C C11' H11D 107.5 . . ? C11' C12' C13' 111.1(8) . . ? C11' C12' H12C 109.4 . . ? C13' C12' H12C 109.4 . . ? C11' C12' H12D 109.4 . . ? C13' C12' H12D 109.4 . . ? H12C C12' H12D 108.0 . . ? C12' C13' H13D 109.5 . . ? C12' C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C12' C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.898(19) 2.01(2) 2.891(3) 166(3) 4_565 N3 H3 O4 0.906(19) 1.96(2) 2.865(4) 177(3) 3_657 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 62.69 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.245 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.048 #====================================================== #====================================================== data_Pbtl_Nbtl_cocryst _database_code_depnum_ccdc_archive 'CCDC 848448' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common 'co-crystal phenobarbital + nembutal' _chemical_melting_point ? _chemical_formula_moiety '(C12 H12 N2 O3), (C11 H18 N2 O3)' _chemical_formula_sum 'C23 H30 N4 O6' _chemical_formula_weight 458.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/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 12.6733(11) _cell_length_b 20.6887(19) _cell_length_c 10.2529(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.458(9) _cell_angle_gamma 90.00 _cell_volume 2363.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3956 _cell_measurement_theta_min 3.9622 _cell_measurement_theta_max 67.2157 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_T_min 0.73360 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_reflns_number 7009 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.08 _diffrn_reflns_theta_max 67.28 _reflns_number_total 2029 _reflns_number_gt 1508 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 1. Molecules of the two crystal components are 50/50 disordered 2. The 1-methylbutyl group of the nembutal molecule is disordered over two positions. >From this, the following disorder components result: component 1 (phenobarbital; fraction 0.50): C9-C10-C11-C12-C13-C14 component 2 (nembutal; fraction 0.27): C9'-C10'-C11'-C12'-C13' component 3 (nembutal; fraction 0.23): C9'-C10"-C11"-C12"-C13" H atoms were not determined for the latter disorder component. ------------------------------------------------------------------------- a) Distance restraints were applied to obtain sensible values for all C(sp3)-C(sp3) bond distances and associated bond angles of the disordered 1-methylbutyl groups: DFIX 1.53 .015 C5 C9' C9' c10' C9' C11' C11' C12' C12' C13' DFIX 1.53 .015 C9' c10" C9' C11" C11" C12" C12" C13" DFIX 2.58 .015 C5 C10' C5 C11' C10' C11' C9' C12' C11' C13' DFIX 2.58 .015 C5 C10" C5 C11" C10" C11" C9' C12" C11" C13" DFIX 2.58 .015 C7 C9 C7 C9' DFIX -2.5 C10' C13' C10" C13" b) Carbon atoms in the same disorder component (phenyl or 1-methylbutyl) were refined with a common isotropic displacement parameter EADP C9 C9' EADP C10 > C14 eadp C10' > C13' EADP C10" > C13" ; _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^)+(0.0010P)^2^+8.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2029 _refine_ls_number_parameters 148 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.1026 _refine_ls_wR_factor_ref 0.1813 _refine_ls_wR_factor_gt 0.1762 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.119 _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 O2 O 1.0648(2) 0.42427(17) 0.6420(2) 0.0693(9) Uani 1 1 d . . . O4 O 0.8417(2) 0.43034(18) 0.1480(2) 0.0763(11) Uani 1 1 d . . . O6 O 0.6670(2) 0.3995(2) 0.4608(3) 0.1088(15) Uani 1 1 d . . . N1 N 0.8648(2) 0.4116(2) 0.5488(3) 0.0652(11) Uani 1 1 d . . . H1 H 0.8736 0.4113 0.6393 0.078 Uiso 1 1 calc R . . N3 N 0.9512(2) 0.42189(17) 0.3940(3) 0.0526(9) Uani 1 1 d . . . H3 H 1.0166 0.4249 0.3847 0.063 Uiso 1 1 calc R . . C2 C 0.9659(3) 0.4193(2) 0.5362(3) 0.0543(10) Uani 1 1 d . . . C4 C 0.8447(3) 0.4202(2) 0.2672(3) 0.0604(12) Uani 1 1 d . A . C5 C 0.7329(3) 0.4021(3) 0.2777(4) 0.0736(14) Uani 1 1 d D . . C6 C 0.7499(3) 0.4042(3) 0.4342(4) 0.0747(15) Uani 1 1 d . A . C7 C 0.6308(3) 0.4473(3) 0.1817(4) 0.101(2) Uani 1 1 d D A . H7A H 0.6225 0.4481 0.0807 0.122 Uiso 1 1 calc R . . H7B H 0.5552 0.4298 0.1738 0.122 Uiso 1 1 calc R . . C8 C 0.6474(4) 0.5159(4) 0.2401(7) 0.112(2) Uani 1 1 d . . . H8A H 0.6413 0.5166 0.3317 0.167 Uiso 1 1 calc R A . H8B H 0.5852 0.5436 0.1658 0.167 Uiso 1 1 calc R . . H8C H 0.7267 0.5317 0.2604 0.167 Uiso 1 1 calc R . . C9 C 0.7229(12) 0.3296(5) 0.2317(18) 0.126(3) Uani 0.50 1 d PGD A 1 C10 C 0.7952(11) 0.2811(7) 0.3256(15) 0.186(4) Uiso 0.50 1 d PGD A 1 H10 H 0.8540 0.2914 0.4241 0.223 Uiso 0.50 1 calc PR A 1 C11 C 0.7814(13) 0.2177(6) 0.2755(18) 0.186(4) Uiso 0.50 1 d PGD A 1 H11 H 0.8308 0.1846 0.3398 0.223 Uiso 0.50 1 calc PR A 1 C12 C 0.6954(14) 0.2027(5) 0.1314(19) 0.186(4) Uiso 0.50 1 d PGD A 1 H12 H 0.6860 0.1594 0.0972 0.223 Uiso 0.50 1 calc PR A 1 C13 C 0.6231(13) 0.2512(8) 0.0375(14) 0.186(4) Uiso 0.50 1 d PGD A 1 H13 H 0.5643 0.2410 -0.0610 0.223 Uiso 0.50 1 calc PR A 1 C14 C 0.6369(12) 0.3147(7) 0.0876(17) 0.186(4) Uiso 0.50 1 d PGD A 1 H14 H 0.5875 0.3478 0.0233 0.223 Uiso 0.50 1 calc PR A 1 C9' C 0.6933(13) 0.3309(5) 0.2208(17) 0.126(3) Uani 0.50 1 d PD A 2 H9' H 0.6119 0.3312 0.2137 0.151 Uiso 0.27 1 calc PR A 2 C10' C 0.656(3) 0.3257(12) 0.0541(19) 0.179(8) Uiso 0.27 1 d PD A 2 H10A H 0.7022 0.3566 0.0295 0.269 Uiso 0.27 1 calc PR A 2 H10B H 0.5700 0.3355 -0.0046 0.269 Uiso 0.27 1 calc PR A 2 H10C H 0.6710 0.2818 0.0316 0.269 Uiso 0.27 1 calc PR A 2 C11' C 0.745(3) 0.2769(7) 0.321(2) 0.179(8) Uiso 0.27 1 d PD A 2 H11A H 0.7159 0.2783 0.3952 0.215 Uiso 0.27 1 calc PR A 2 H11B H 0.8331 0.2823 0.3749 0.215 Uiso 0.27 1 calc PR A 2 C12' C 0.715(3) 0.2087(7) 0.245(4) 0.179(8) Uiso 0.27 1 d PD A 2 H12A H 0.7051 0.1771 0.3105 0.215 Uiso 0.27 1 calc PR A 2 H12B H 0.6383 0.2110 0.1509 0.215 Uiso 0.27 1 calc PR A 2 C13' C 0.815(3) 0.1859(16) 0.212(4) 0.179(8) Uiso 0.27 1 d PD A 2 H13A H 0.8142 0.2122 0.1318 0.269 Uiso 0.27 1 calc PR A 2 H13B H 0.8017 0.1404 0.1812 0.269 Uiso 0.27 1 calc PR A 2 H13C H 0.8927 0.1904 0.3012 0.269 Uiso 0.27 1 calc PR A 2 C10" C 0.805(3) 0.2858(11) 0.280(7) 0.230(13) Uiso 0.23 1 d PD B 3 C11" C 0.600(4) 0.3061(13) 0.267(5) 0.230(13) Uiso 0.23 1 d PD C 3 C12" C 0.552(4) 0.2390(16) 0.202(6) 0.230(13) Uiso 0.23 1 d PD . 3 C13" C 0.590(6) 0.219(2) 0.086(6) 0.230(13) Uiso 0.23 1 d PD D 3 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 O2 0.0419(13) 0.140(3) 0.0276(11) -0.0046(13) 0.0179(11) -0.0111(15) O4 0.0400(13) 0.169(3) 0.0258(11) -0.0031(14) 0.0200(10) -0.0032(16) O6 0.0403(14) 0.254(5) 0.0407(14) 0.006(2) 0.0262(12) -0.007(2) N1 0.0400(15) 0.137(3) 0.0268(13) -0.0017(16) 0.0223(12) -0.0043(17) N3 0.0361(13) 0.103(3) 0.0246(12) -0.0037(14) 0.0192(11) -0.0060(14) C2 0.0394(17) 0.100(3) 0.0283(15) -0.0044(17) 0.0203(14) -0.0064(18) C4 0.0391(18) 0.118(4) 0.0287(15) -0.0091(18) 0.0200(14) -0.0062(19) C5 0.0440(19) 0.151(5) 0.0327(17) -0.016(2) 0.0239(15) -0.025(2) C6 0.0397(18) 0.156(5) 0.0350(17) -0.003(2) 0.0230(15) -0.012(2) C7 0.0283(19) 0.242(8) 0.0316(19) 0.006(3) 0.0122(16) -0.009(3) C8 0.045(3) 0.202(8) 0.091(4) 0.044(4) 0.035(3) 0.014(3) C9 0.107(7) 0.203(8) 0.096(5) -0.061(5) 0.072(5) -0.090(6) C9' 0.107(7) 0.203(8) 0.096(5) -0.061(5) 0.072(5) -0.090(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.209(4) . ? O4 C4 1.223(4) . ? O6 C6 1.208(4) . ? N1 C2 1.357(4) . ? N1 C6 1.377(4) . ? N3 C4 1.357(4) . ? N3 C2 1.381(4) . ? C4 C5 1.518(5) . ? C5 C6 1.515(5) . ? C5 C7 1.518(7) . ? C5 C9 1.558(12) . ? C5 C9' 1.576(10) . ? C7 C8 1.516(9) . ? C9 C10 1.3900 . ? C9 C14 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C9' C11' 1.445(12) . ? C9' C10' 1.543(12) . ? C11' C12' 1.570(14) . ? C12' C13' 1.532(15) . ? C11" C12" 1.534(14) . ? C12" C13" 1.549(15) . ? C12" C12" 1.97(7) 2_655 ? 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 N1 C6 126.5(3) . . ? C4 N3 C2 125.7(3) . . ? O2 C2 N1 123.2(3) . . ? O2 C2 N3 120.3(3) . . ? N1 C2 N3 116.5(3) . . ? O4 C4 N3 119.7(3) . . ? O4 C4 C5 121.9(3) . . ? N3 C4 C5 118.3(3) . . ? C6 C5 C4 113.7(3) . . ? C6 C5 C7 108.4(4) . . ? C4 C5 C7 109.8(4) . . ? C6 C5 C9 107.4(6) . . ? C4 C5 C9 99.2(4) . . ? C7 C5 C9 118.4(7) . . ? C6 C5 C9' 106.2(6) . . ? C4 C5 C9' 110.4(6) . . ? C7 C5 C9' 108.3(6) . . ? C9 C5 C9' 12.3(8) . . ? O6 C6 N1 119.7(3) . . ? O6 C6 C5 122.5(3) . . ? N1 C6 C5 117.8(3) . . ? C8 C7 C5 114.0(4) . . ? C10 C9 C14 120.0 . . ? C10 C9 C5 123.5(10) . . ? C14 C9 C5 116.5(10) . . ? C9 C10 C11 120.0 . . ? C12 C11 C10 120.0 . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C9 120.0 . . ? C11' C9' C10' 122.1(11) . . ? C11' C9' C5 120.2(11) . . ? C10' C9' C5 110.5(10) . . ? C9' C11' C12' 114.8(14) . . ? C13' C12' C11' 111.0(14) . . ? C11" C12" C13" 111.2(14) . . ? C11" C12" C12" 90.7(18) . 2_655 ? C13" C12" C12" 156(4) . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O4 0.88 1.98 2.860(3) 176.8 2_755 N1 H1 O2 0.88 2.01 2.867(3) 164.1 2_756 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 67.28 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.515 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.053 data_Nbtl-II _database_code_depnum_ccdc_archive 'CCDC 854425' #TrackingRef 'Nbtl-II.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'nembutal, pentobarbital' _chemical_melting_point ? _chemical_formula_moiety 'C11 H18 N2 O3' _chemical_formula_sum 'C11 H18 N2 O3' _chemical_formula_weight 226.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8675(10) _cell_length_b 21.824(3) _cell_length_c 10.2201(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.476(9) _cell_angle_gamma 90.00 _cell_volume 2479.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2189 _cell_measurement_theta_min 3.9729 _cell_measurement_theta_max 66.8912 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.729 _exptl_absorpt_correction_T_min 0.97678 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.3575 _diffrn_reflns_number 16190 _diffrn_reflns_av_R_equivalents 0.0777 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 67.00 _reflns_number_total 4337 _reflns_number_gt 2291 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Disorder of 1-methylbutyl groups: molecule 1: disorder of the 1-methyl group between C10 and C10B (10:30) molecule 2 a) conformation A disorder between methyl groups C13 and C13C: C10-C9-C11-c12-C13 (42%) and C10-C9-C11-c12-C13 (43%) b) conformation B (15%) C10A-C9-C11A-C12A-C13A ------------------------------------------------------------------- C(sp3) bond distances and associated angles of the disordered 1-methylbutyl groups: DFIX 1.52 .01 C9 C10 C9 C11 C11 C12 C12 C13 DFIX 1.52 .01 C9 C10A C9 C11A C11A C12A C12A C13A DFIX 1.52 .01 C9' C10' C9' C11' C11' C12' C12' C13' C9' C10B DFIX 2.55 .02 C7 C9 C5 C10 C5 C11 C9 C12 C11 C13 C10 C11 DFIX 2.55 .02 C5 C10A C5 C11A C9 C12A C11A C13A C10A C11A DFIX 2.55 .02 C7' C9' C5' C10' C5' C11' C9' C12' C11' C13' DFIX 2.55 .02 C5' C10B C10B C11' b) Antibumping restraints were used to obtain sensible conformations of disordered chains: DFIX -1.85 H13D H10D DFIX -1.85 H13D H10E DFIX -1.85 H13D H10F DFIX -1.85 H13E H10D DFIX -1.85 H13E H10E DFIX -1.85 H13E H10F DFIX -1.85 H13F H10D DFIX -1.85 H13F H10E DFIX -1.85 H13F H10F c) H atoms attached N were included in the refinement with isotropic U(iso) values and an N-H distance restraint of 0.88(2) %A was applied: DFIX 0.88 .02 N1 H1 N3 H3 N1' H1' N3' H3' ; _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^)+(0.0017P)^2^+3.7690P] 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 4337 _refine_ls_number_parameters 338 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.1538 _refine_ls_R_factor_gt 0.0874 _refine_ls_wR_factor_ref 0.1469 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.101 _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 O2 O 0.6257(2) 0.32953(16) -0.0317(3) 0.0623(9) Uani 1 1 d . . . O6 O 0.2252(3) 0.34877(17) -0.2468(3) 0.0683(10) Uani 1 1 d . . . O4 O 0.3985(2) 0.31132(18) 0.2388(3) 0.0719(11) Uani 1 1 d . . . N1 N 0.4241(3) 0.33710(18) -0.1375(3) 0.0495(9) Uani 1 1 d D . . H1 H 0.434(3) 0.3287(18) -0.216(2) 0.045(11) Uiso 1 1 d D . . N3 N 0.5099(3) 0.32606(19) 0.1033(3) 0.0500(10) Uani 1 1 d D . . H3 H 0.566(2) 0.3177(17) 0.185(2) 0.041(11) Uiso 1 1 d D . . C2 C 0.5253(3) 0.3313(2) -0.0237(4) 0.0482(11) Uani 1 1 d . . . C4 C 0.4014(3) 0.3241(2) 0.1235(4) 0.0559(12) Uani 1 1 d . . . C5 C 0.2887(4) 0.3410(2) 0.0028(4) 0.0556(12) Uani 1 1 d D B . C6 C 0.3075(4) 0.3423(2) -0.1390(4) 0.0492(11) Uani 1 1 d . . . C7 C 0.1885(4) 0.2940(3) -0.0095(4) 0.0733(18) Uani 1 1 d D . . H7A H 0.1806 0.2895 0.0833 0.088 Uiso 1 1 calc R . . H7B H 0.1114 0.3105 -0.0741 0.088 Uiso 1 1 calc R . . C8 C 0.2080(4) 0.2310(3) -0.0607(5) 0.0755(16) Uani 1 1 d . . . H8A H 0.2130 0.2345 -0.1541 0.113 Uiso 1 1 calc R . . H8B H 0.1405 0.2042 -0.0647 0.113 Uiso 1 1 calc R . . H8C H 0.2830 0.2135 0.0036 0.113 Uiso 1 1 calc R . . C9 C 0.2481(5) 0.4071(3) 0.0276(6) 0.094(2) Uani 1 1 d D . . H9 H 0.1811 0.4190 -0.0597 0.113 Uiso 0.85 1 calc PR A 1 H9A H 0.3257 0.4299 0.0671 0.113 Uiso 0.15 1 calc PR A 2 C10 C 0.1957(12) 0.4070(5) 0.1470(11) 0.161(5) Uani 0.85 1 d PD B 1 H10A H 0.2579 0.3938 0.2341 0.242 Uiso 0.85 1 calc PR B 1 H10B H 0.1274 0.3786 0.1235 0.242 Uiso 0.85 1 calc PR B 1 H10C H 0.1687 0.4484 0.1588 0.242 Uiso 0.85 1 calc PR B 1 C11 C 0.3451(7) 0.4538(3) 0.0504(9) 0.115(3) Uani 0.85 1 d PD B 1 H11A H 0.3767 0.4517 -0.0272 0.138 Uiso 0.85 1 calc PR B 1 H11B H 0.4120 0.4444 0.1383 0.138 Uiso 0.85 1 calc PR B 1 C12 C 0.2990(11) 0.5186(4) 0.0587(10) 0.170(5) Uani 0.85 1 d PD B 1 H12A H 0.3578 0.5488 0.0488 0.204 Uiso 0.85 1 calc PRD B 1 H12B H 0.2915 0.5248 0.1513 0.204 Uiso 0.85 1 calc PRD B 1 C13 C 0.1759(14) 0.5295(9) -0.057(2) 0.154(8) Uiso 0.42 1 d PD B 1 H13A H 0.1692 0.5726 -0.0854 0.231 Uiso 0.42 1 calc PR B 1 H13B H 0.1116 0.5195 -0.0208 0.231 Uiso 0.42 1 calc PR B 1 H13C H 0.1687 0.5034 -0.1371 0.231 Uiso 0.42 1 calc PR B 1 C13C C 0.2411(17) 0.5359(9) -0.0918(17) 0.133(7) Uiso 0.43 1 d PD C 3 H13G H 0.288(8) 0.519(5) -0.144(3) 0.200 Uiso 0.43 1 d PD D 3 H13H H 0.239(11) 0.5805(10) -0.099(3) 0.200 Uiso 0.43 1 d PD E 3 H13I H 0.159(5) 0.519(6) -0.126(5) 0.200 Uiso 0.43 1 d PD F 3 C10A C 0.181(6) 0.4417(19) -0.105(3) 0.209(19) Uiso 0.15 1 d PD B 2 H10D H 0.1372 0.4759 -0.0839 0.313 Uiso 0.15 1 calc PRD B 2 H10E H 0.1248 0.4141 -0.1721 0.313 Uiso 0.15 1 calc PRD B 2 H10F H 0.2392 0.4576 -0.1459 0.313 Uiso 0.15 1 calc PRD B 2 C11A C 0.191(7) 0.415(2) 0.138(6) 0.209(19) Uiso 0.15 1 d PD B 2 H11C H 0.2510 0.4046 0.2310 0.251 Uiso 0.15 1 calc PR B 2 H11D H 0.1229 0.3859 0.1194 0.251 Uiso 0.15 1 calc PR B 2 C12A C 0.146(5) 0.4804(17) 0.141(6) 0.209(19) Uiso 0.15 1 d PD B 2 H12C H 0.1816 0.4966 0.2376 0.251 Uiso 0.15 1 calc PR B 2 H12D H 0.1749 0.5063 0.0800 0.251 Uiso 0.15 1 calc PR B 2 C13A C 0.009(5) 0.486(3) 0.094(7) 0.209(19) Uiso 0.15 1 d PD B 2 H13D H -0.0137 0.5291 0.0768 0.313 Uiso 0.15 1 calc PRD B 2 H13E H -0.0180 0.4700 0.1678 0.313 Uiso 0.15 1 calc PRD B 2 H13F H -0.0275 0.4622 0.0086 0.313 Uiso 0.15 1 calc PRD B 2 O2' O 0.4953(2) 0.18032(16) 0.1238(3) 0.0608(9) Uani 1 1 d . . . O4' O 0.7154(2) 0.19334(16) -0.1513(3) 0.0629(9) Uani 1 1 d . . . O6' O 0.8916(2) 0.14752(18) 0.3299(3) 0.0712(10) Uani 1 1 d . . . N1' N 0.6955(3) 0.16361(17) 0.2254(3) 0.0449(9) Uani 1 1 d D . . H1' H 0.685(3) 0.1550(18) 0.305(2) 0.050(12) Uiso 1 1 d D . . N3' N 0.6080(3) 0.18267(18) -0.0119(3) 0.0483(9) Uani 1 1 d D . . H3' H 0.5368(15) 0.1833(15) -0.079(2) 0.024(9) Uiso 1 1 d D . . C2' C 0.5933(3) 0.1755(2) 0.1154(4) 0.0438(10) Uani 1 1 d . . . C4' C 0.7146(3) 0.1809(2) -0.0355(4) 0.0492(11) Uani 1 1 d . . . C5' C 0.8265(3) 0.1608(2) 0.0823(4) 0.0498(11) Uani 1 1 d D H . C6' C 0.8085(3) 0.1566(2) 0.2221(4) 0.0479(11) Uani 1 1 d . . . C7' C 0.9289(3) 0.2064(2) 0.0945(4) 0.0595(14) Uani 1 1 d D . . H7'1 H 1.0052 0.1897 0.1603 0.071 Uiso 1 1 calc R . . H7'2 H 0.9377 0.2105 0.0020 0.071 Uiso 1 1 calc R . . C8' C 0.9075(4) 0.2693(3) 0.1446(5) 0.0746(16) Uani 1 1 d . . . H8'1 H 0.8297 0.2851 0.0832 0.112 Uiso 1 1 calc R . . H8'2 H 0.9716 0.2972 0.1427 0.112 Uiso 1 1 calc R . . H8'3 H 0.9074 0.2662 0.2402 0.112 Uiso 1 1 calc R . . C9' C 0.8571(4) 0.0949(2) 0.0432(5) 0.0686(14) Uani 1 1 d D . . H9' H 0.9186 0.0780 0.1297 0.082 Uiso 0.70 1 calc PR G 1 H9'B H 0.8783 0.0983 -0.0430 0.082 Uiso 0.30 1 calc PR G 2 C10' C 0.9187(7) 0.0967(4) -0.0692(8) 0.092(2) Uani 0.70 1 d PD H 1 H10U H 0.9960 0.1181 -0.0310 0.138 Uiso 0.70 1 calc PR H 1 H10V H 0.8666 0.1185 -0.1522 0.138 Uiso 0.70 1 calc PR H 1 H10W H 0.9320 0.0548 -0.0948 0.138 Uiso 0.70 1 calc PR H 1 C11' C 0.7477(5) 0.0532(2) 0.0107(6) 0.0868(18) Uani 1 1 d D H . H11X H 0.7165 0.0563 0.0885 0.104 Uiso 1 1 calc R . . H11Y H 0.6843 0.0687 -0.0744 0.104 Uiso 1 1 calc R . . C12' C 0.7688(6) -0.0135(3) -0.0114(8) 0.112(2) Uani 1 1 d D . . H12X H 0.8286 -0.0306 0.0748 0.134 Uiso 1 1 calc R H . H12Y H 0.8017 -0.0175 -0.0876 0.134 Uiso 1 1 calc R . . C13' C 0.6527(8) -0.0494(3) -0.0483(9) 0.143(3) Uani 1 1 d D H . H13X H 0.6194 -0.0448 0.0265 0.215 Uiso 1 1 calc R . . H13Y H 0.6685 -0.0928 -0.0593 0.215 Uiso 1 1 calc R . . H13Z H 0.5948 -0.0337 -0.1359 0.215 Uiso 1 1 calc R . . C10B C 0.9628(11) 0.0647(8) 0.1570(15) 0.092(2) Uani 0.30 1 d PD H 2 H10X H 0.9771 0.0858 0.2460 0.138 Uiso 0.30 1 calc PR H 2 H10Y H 1.0350 0.0675 0.1317 0.138 Uiso 0.30 1 calc PR H 2 H10Z H 0.9440 0.0216 0.1663 0.138 Uiso 0.30 1 calc PR H 2 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 O2 0.0399(16) 0.112(3) 0.0371(15) 0.0041(17) 0.0159(12) 0.0081(16) O6 0.0425(16) 0.119(3) 0.0333(15) 0.0083(17) 0.0011(13) -0.0061(18) O4 0.0394(16) 0.148(3) 0.0292(15) -0.0050(18) 0.0128(12) -0.0040(18) N1 0.0387(18) 0.081(3) 0.0278(17) 0.0021(18) 0.0100(14) 0.0028(18) N3 0.0349(18) 0.091(3) 0.0239(16) -0.0007(18) 0.0106(14) 0.0001(18) C2 0.038(2) 0.070(3) 0.035(2) 0.001(2) 0.0101(17) 0.001(2) C4 0.037(2) 0.091(4) 0.038(2) -0.010(2) 0.0113(18) 0.002(2) C5 0.039(2) 0.089(4) 0.035(2) -0.009(2) 0.0081(17) 0.008(2) C6 0.042(2) 0.067(3) 0.036(2) 0.000(2) 0.0098(18) 0.000(2) C7 0.027(2) 0.166(6) 0.028(2) 0.011(3) 0.0100(17) 0.006(3) C8 0.047(3) 0.101(5) 0.068(3) 0.008(3) 0.007(2) -0.004(3) C9 0.089(4) 0.115(5) 0.068(4) -0.024(4) 0.014(3) 0.034(4) C10 0.172(10) 0.201(11) 0.115(7) -0.054(7) 0.057(7) 0.078(9) C11 0.111(6) 0.068(5) 0.138(7) -0.023(5) 0.008(5) 0.017(5) C12 0.262(15) 0.090(7) 0.118(8) -0.002(6) 0.015(8) -0.006(8) O2' 0.0351(15) 0.111(3) 0.0378(15) 0.0049(16) 0.0148(12) 0.0046(16) O4' 0.0400(16) 0.117(3) 0.0323(15) 0.0035(16) 0.0134(12) -0.0007(16) O6' 0.0405(16) 0.129(3) 0.0407(17) 0.0158(18) 0.0098(14) 0.0042(18) N1' 0.0353(17) 0.071(3) 0.0264(16) 0.0006(17) 0.0085(14) -0.0031(17) N3' 0.0246(16) 0.087(3) 0.0283(17) 0.0009(17) 0.0029(14) 0.0012(17) C2' 0.037(2) 0.065(3) 0.029(2) -0.0033(19) 0.0116(17) -0.002(2) C4' 0.034(2) 0.084(4) 0.028(2) -0.004(2) 0.0089(16) 0.000(2) C5' 0.036(2) 0.078(3) 0.035(2) -0.005(2) 0.0118(17) 0.010(2) C6' 0.033(2) 0.075(3) 0.032(2) -0.003(2) 0.0063(17) 0.001(2) C7' 0.031(2) 0.110(4) 0.038(2) 0.004(2) 0.0128(18) -0.002(2) C8' 0.042(3) 0.096(4) 0.078(3) 0.012(3) 0.013(2) -0.006(3) C9' 0.056(3) 0.088(4) 0.058(3) -0.007(3) 0.015(2) 0.010(3) C10' 0.080(5) 0.112(7) 0.097(6) -0.007(5) 0.048(4) 0.011(5) C11' 0.089(4) 0.084(4) 0.085(4) -0.022(3) 0.027(3) 0.012(3) C12' 0.129(6) 0.107(6) 0.115(6) -0.008(4) 0.062(5) 0.011(5) C13' 0.186(9) 0.097(6) 0.164(8) -0.043(6) 0.084(7) -0.034(6) C10B 0.080(5) 0.112(7) 0.097(6) -0.007(5) 0.048(4) 0.011(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 O2 C2 1.223(4) . ? O6 C6 1.198(5) . ? O4 C4 1.223(5) . ? N1 C2 1.354(5) . ? N1 C6 1.383(5) . ? N1 H1 0.872(10) . ? N3 C4 1.374(5) . ? N3 C2 1.377(5) . ? N3 H3 0.890(10) . ? C4 C5 1.514(6) . ? C5 C6 1.542(5) . ? C5 C7 1.543(7) . ? C5 C9 1.568(7) . ? C7 C8 1.518(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.493(7) . ? C9 C10A 1.513(10) . ? C9 C11A 1.518(10) . ? C9 C10 1.551(7) . ? C9 H9 1.0000 . ? C9 H9A 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.530(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.541(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13C H13G 0.976(10) . ? C13C H13H 0.975(10) . ? C13C H13I 0.977(10) . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? C11A C12A 1.533(10) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A C13A 1.525(11) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? O2' C2' 1.200(4) . ? O4' C4' 1.218(4) . ? O6' C6' 1.211(4) . ? N1' C2' 1.360(5) . ? N1' C6' 1.362(5) . ? N1' H1' 0.878(10) . ? N3' C4' 1.369(5) . ? N3' C2' 1.381(5) . ? N3' H3' 0.881(10) . ? C4' C5' 1.512(5) . ? C5' C6' 1.520(5) . ? C5' C7' 1.542(6) . ? C5' C9' 1.568(6) . ? C7' C8' 1.518(7) . ? C7' H7'1 0.9900 . ? C7' H7'2 0.9900 . ? C8' H8'1 0.9800 . ? C8' H8'2 0.9800 . ? C8' H8'3 0.9800 . ? C9' C11' 1.524(6) . ? C9' C10B 1.530(9) . ? C9' C10' 1.563(7) . ? C9' H9' 1.0000 . ? C9' H9'B 1.0000 . ? C10' H10U 0.9800 . ? C10' H10V 0.9800 . ? C10' H10W 0.9800 . ? C11' C12' 1.508(6) . ? C11' H11X 0.9900 . ? C11' H11Y 0.9900 . ? C12' C13' 1.513(7) . ? C12' H12X 0.9900 . ? C12' H12Y 0.9900 . ? C13' H13X 0.9800 . ? C13' H13Y 0.9800 . ? C13' H13Z 0.9800 . ? C10B H10X 0.9800 . ? C10B H10Y 0.9800 . ? C10B H10Z 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 N1 C6 126.9(3) . . ? C2 N1 H1 114(3) . . ? C6 N1 H1 118(3) . . ? C4 N3 C2 125.8(3) . . ? C4 N3 H3 107(2) . . ? C2 N3 H3 127(2) . . ? O2 C2 N1 122.5(3) . . ? O2 C2 N3 120.9(3) . . ? N1 C2 N3 116.5(3) . . ? O4 C4 N3 119.7(4) . . ? O4 C4 C5 121.8(4) . . ? N3 C4 C5 118.5(4) . . ? C4 C5 C6 113.1(3) . . ? C4 C5 C7 109.9(4) . . ? C6 C5 C7 107.2(3) . . ? C4 C5 C9 109.0(4) . . ? C6 C5 C9 106.8(4) . . ? C7 C5 C9 110.7(4) . . ? O6 C6 N1 120.7(4) . . ? O6 C6 C5 121.8(4) . . ? N1 C6 C5 117.5(3) . . ? C8 C7 C5 115.2(4) . . ? C8 C7 H7A 108.5 . . ? C5 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C5 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10A 86(3) . . ? C11 C9 C11A 109(3) . . ? C10A C9 C11A 112.6(15) . . ? C11 C9 C10 112.2(7) . . ? C10A C9 C10 119(2) . . ? C11A C9 C10 7.0(13) . . ? C11 C9 C5 112.9(5) . . ? C10A C9 C5 114.1(14) . . ? C11A C9 C5 117.7(14) . . ? C10 C9 C5 110.9(5) . . ? C11 C9 H9 106.8 . . ? C10A C9 H9 21.0 . . ? C11A C9 H9 102.3 . . ? C10 C9 H9 106.8 . . ? C5 C9 H9 106.8 . . ? C11 C9 H9A 17.4 . . ? C10A C9 H9A 103.4 . . ? C11A C9 H9A 103.4 . . ? C10 C9 H9A 104.4 . . ? C5 C9 H9A 103.4 . . ? H9 C9 H9A 124.2 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? C9 C11 C12 111.7(7) . . ? C9 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C9 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 111.2(9) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 H13H 84(3) . . ? H13A C13 H13H 36.1 . . ? H13B C13 H13H 144.4 . . ? H13C C13 H13H 95.5 . . ? C12 C13 H13I 125(9) . . ? H13A C13 H13I 91.8 . . ? H13B C13 H13I 109.3 . . ? H13C C13 H13I 19.6 . . ? H13H C13 H13I 86(5) . . ? H13G C13C H13H 110.3(15) . . ? H13G C13C H13I 110.3(15) . . ? H13H C13C H13I 110.2(15) . . ? C9 C10A H10D 109.5 . . ? C9 C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? C9 C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? C9 C11A C12A 111.6(15) . . ? C9 C11A H11C 109.3 . . ? C12A C11A H11C 109.3 . . ? C9 C11A H11D 109.3 . . ? C12A C11A H11D 109.3 . . ? H11C C11A H11D 108.0 . . ? C13A C12A C11A 114.1(17) . . ? C13A C12A H12C 108.7 . . ? C11A C12A H12C 108.7 . . ? C13A C12A H12D 108.7 . . ? C11A C12A H12D 108.7 . . ? H12C C12A H12D 107.6 . . ? C12A C13A H13D 109.5 . . ? C12A C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C12A C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C2' N1' C6' 127.0(3) . . ? C2' N1' H1' 116(3) . . ? C6' N1' H1' 117(3) . . ? C4' N3' C2' 126.3(3) . . ? C4' N3' H3' 124(2) . . ? C2' N3' H3' 109(2) . . ? O2' C2' N1' 124.3(3) . . ? O2' C2' N3' 120.1(3) . . ? N1' C2' N3' 115.5(3) . . ? O4' C4' N3' 119.2(3) . . ? O4' C4' C5' 122.3(3) . . ? N3' C4' C5' 118.5(3) . . ? C4' C5' C6' 113.1(3) . . ? C4' C5' C7' 109.0(4) . . ? C6' C5' C7' 109.2(3) . . ? C4' C5' C9' 106.2(3) . . ? C6' C5' C9' 107.8(4) . . ? C7' C5' C9' 111.5(3) . . ? O6' C6' N1' 119.4(3) . . ? O6' C6' C5' 121.8(3) . . ? N1' C6' C5' 118.7(3) . . ? C8' C7' C5' 113.0(3) . . ? C8' C7' H7'1 109.0 . . ? C5' C7' H7'1 109.0 . . ? C8' C7' H7'2 109.0 . . ? C5' C7' H7'2 109.0 . . ? H7'1 C7' H7'2 107.8 . . ? C7' C8' H8'1 109.5 . . ? C7' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C7' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? C11' C9' C10B 108.5(7) . . ? C11' C9' C10' 115.9(5) . . ? C10B C9' C10' 95.7(8) . . ? C11' C9' C5' 110.4(4) . . ? C10B C9' C5' 113.7(7) . . ? C10' C9' C5' 111.9(5) . . ? C11' C9' H9' 106.0 . . ? C10B C9' H9' 10.7 . . ? C10' C9' H9' 106.0 . . ? C5' C9' H9' 106.0 . . ? C11' C9' H9'B 108.0 . . ? C10B C9' H9'B 108.0 . . ? C10' C9' H9'B 12.6 . . ? C5' C9' H9'B 108.0 . . ? H9' C9' H9'B 118.4 . . ? C9' C10' H10U 109.5 . . ? C9' C10' H10V 109.5 . . ? C9' C10' H10W 109.5 . . ? C12' C11' C9' 115.9(5) . . ? C12' C11' H11X 108.3 . . ? C9' C11' H11X 108.3 . . ? C12' C11' H11Y 108.3 . . ? C9' C11' H11Y 108.3 . . ? H11X C11' H11Y 107.4 . . ? C11' C12' C13' 110.6(5) . . ? C11' C12' H12X 109.5 . . ? C13' C12' H12X 109.5 . . ? C11' C12' H12Y 109.5 . . ? C13' C12' H12Y 109.5 . . ? H12X C12' H12Y 108.1 . . ? C12' C13' H13X 109.5 . . ? C12' C13' H13Y 109.5 . . ? H13X C13' H13Y 109.5 . . ? C12' C13' H13Z 109.5 . . ? H13X C13' H13Z 109.5 . . ? H13Y C13' H13Z 109.5 . . ? C9' C10B H10X 109.5 . . ? C9' C10B H10Y 109.5 . . ? H10X C10B H10Y 109.5 . . ? C9' C10B H10Z 109.5 . . ? H10X C10B H10Z 109.5 . . ? H10Y C10B H10Z 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2' 0.872(10) 2.018(14) 2.872(4) 166(4) 4_565 N3 H3 O4' 0.890(10) 1.977(14) 2.853(4) 168(3) 4_566 N1' H1' O2 0.878(10) 2.06(2) 2.883(4) 155(4) 4_566 N3' H3' O4 0.881(10) 2.011(13) 2.873(4) 166(3) 4_565 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.350 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.049