# Supplementary Material (ESI) for PCCP # This journal is © the Owner Societies 2010 data_global _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Graeme Day' 'Bjorn Dalhus' 'Carl Henrik Gorbitz' _publ_contact_author_name 'Graeme Day' _publ_contact_author_email GMD27@CAM.AC.UK _publ_section_title ; Pseudoracemic amino acid complexes: blind predictions for flexible two-component crystals ; # Attachment 'C004055J.cif' ############################################################################## ### CIF submission form for molecular structure report (Acta Cryst. C) ### ### Version: 2.0.2 (6 July 1998) ### ############################################################################## #============================================================================== data_I _database_code_depnum_ccdc_archive 'CCDC 772920' #TrackingRef 'C004055J.cif' _audit_creation_method SHELXL _chemical_name_systematic ; (S,R)-2-amino-3-methylpentanoic acid:R-2-amino-4-methylpentaoic acid ; _chemical_name_common L-allo-isoleucine:D-leucine _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 N O2, C6 H13 N O2' _chemical_formula_sum 'C12 H26 N2 O4' _chemical_formula_weight 262.35 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.23570(10) _cell_length_b 5.42510(10) _cell_length_c 13.5733(2) _cell_angle_alpha 87.4160(10) _cell_angle_beta 88.9940(10) _cell_angle_gamma 69.4310(10) _cell_volume 360.593(11) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 40.51 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method ? _exptl_crystal_F_000 144 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8000 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'Sets of exposures each taken over 0.3\% \w rotation' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9984 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 40.51 _reflns_number_total 6493 _reflns_number_observed 5779 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT+ (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement 'SHELXTL (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Data were collected by measuring six sets of exposures with the detector set at 2\q = 29\% and 65\%, crystal-to-detector distance 5.00 cm. Refinement of F^2^ against ALL reflections. ; _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^)+(0.0629P)^2^+0.0000P] 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_extinction_coef ? _refine_ls_number_reflns 6493 _refine_ls_number_parameters 185 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.74840(13) 0.14953(12) 0.41165(5) 0.01588(12) Uani 1 1 d . . . O2A O 0.29891(13) 0.28757(13) 0.37909(5) 0.01542(12) Uani 1 1 d . . . N1A N 0.75692(15) 0.63855(14) 0.42164(6) 0.01264(12) Uani 1 1 d . . . H1A H 0.922(4) 0.532(3) 0.3989(12) 0.019 Uiso 1 1 d . . . H2A H 0.760(3) 0.816(3) 0.4147(12) 0.019 Uiso 1 1 d . . . H3A H 0.754(3) 0.593(3) 0.4877(13) 0.019 Uiso 1 1 d . . . C1A C 0.52219(17) 0.32454(15) 0.38869(6) 0.01140(13) Uani 1 1 d . . . C2A C 0.51945(16) 0.60869(15) 0.36996(6) 0.01174(13) Uani 1 1 d . . . H21A H 0.3482 0.7321 0.3993 0.014 Uiso 1 1 calc R . . C3A C 0.52317(19) 0.68622(17) 0.25843(7) 0.01454(14) Uani 1 1 d . . . H31A H 0.5940 0.8351 0.2522 0.017 Uiso 1 1 calc R . . C4A C 0.2315(2) 0.7872(2) 0.21765(8) 0.0260(2) Uani 1 1 d . . . H41A H 0.1127 0.9203 0.2608 0.039 Uiso 1 1 calc R . . H42A H 0.1647 0.6401 0.2150 0.039 Uiso 1 1 calc R . . H43A H 0.2308 0.8658 0.1512 0.039 Uiso 1 1 calc R . . C5A C 0.7149(2) 0.45859(19) 0.19917(7) 0.01985(16) Uani 1 1 d . . . H51A H 0.8959 0.3911 0.2314 0.024 Uiso 1 1 calc R . . H52A H 0.6415 0.3133 0.2006 0.024 Uiso 1 1 calc R . . C6A C 0.7506(3) 0.5391(3) 0.09120(8) 0.0325(2) Uani 1 1 d . . . H61A H 0.8870 0.3912 0.0592 0.049 Uiso 1 1 calc R . . H62A H 0.8116 0.6906 0.0890 0.049 Uiso 1 1 calc R . . H63A H 0.5761 0.5867 0.0566 0.049 Uiso 1 1 calc R . . O1B O 0.14965(14) 0.60259(13) 0.58726(6) 0.01704(13) Uani 1 1 d . . . O2B O 0.60283(13) 0.45593(13) 0.61426(5) 0.01617(12) Uani 1 1 d . . . N1B N 0.15115(16) 0.10668(15) 0.57107(6) 0.01342(13) Uani 1 1 d . . . H1B H -0.023(4) 0.217(3) 0.5881(12) 0.020 Uiso 1 1 d . . . H2B H 0.162(4) -0.055(3) 0.5779(12) 0.020 Uiso 1 1 d . . . H3B H 0.170(4) 0.145(3) 0.5113(13) 0.020 Uiso 1 1 d . . . C1B C 0.37550(17) 0.42484(16) 0.60906(6) 0.01152(13) Uani 1 1 d . . . C2B C 0.36658(17) 0.14615(15) 0.63334(6) 0.01182(13) Uani 1 1 d . . . H21B H 0.5480 0.0100 0.6189 0.014 Uiso 1 1 calc R . . C3B C 0.2912(2) 0.11763(19) 0.74248(7) 0.01649(15) Uani 1 1 d . . . H31B H 0.1258 0.2695 0.7579 0.020 Uiso 1 1 calc R . . H32B H 0.2449 -0.0439 0.7518 0.020 Uiso 1 1 calc R . . C4B C 0.5158(2) 0.10284(19) 0.81633(7) 0.01989(16) Uani 1 1 d . . . H41B H 0.5978 0.2380 0.7955 0.024 Uiso 1 1 calc R . . C5B C 0.3897(3) 0.1662(3) 0.91957(9) 0.0370(3) Uani 1 1 d . . . H51B H 0.2584 0.3470 0.9184 0.056 Uiso 1 1 calc R . . H52B H 0.5342 0.1485 0.9672 0.056 Uiso 1 1 calc R . . H53B H 0.2963 0.0434 0.9388 0.056 Uiso 1 1 calc R . . C6B C 0.7423(2) -0.1697(2) 0.81897(9) 0.0275(2) Uani 1 1 d . . . H61B H 0.8137 -0.2120 0.7522 0.041 Uiso 1 1 calc R . . H62B H 0.6679 -0.3027 0.8442 0.041 Uiso 1 1 calc R . . H63B H 0.8898 -0.1684 0.8621 0.041 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 O1A 0.0143(3) 0.0093(2) 0.0235(3) 0.0011(2) -0.0036(2) -0.0035(2) O2A 0.0131(3) 0.0143(3) 0.0204(3) -0.0014(2) 0.0017(2) -0.0067(2) N1A 0.0134(3) 0.0090(3) 0.0156(3) 0.0001(2) -0.0013(2) -0.0041(2) C1A 0.0131(3) 0.0091(3) 0.0122(3) -0.0011(2) 0.0015(2) -0.0041(3) C2A 0.0115(3) 0.0089(3) 0.0147(3) -0.0006(2) 0.0002(2) -0.0034(3) C3A 0.0159(3) 0.0123(3) 0.0154(3) 0.0024(3) -0.0013(2) -0.0054(3) C4A 0.0191(4) 0.0288(5) 0.0261(5) 0.0079(4) -0.0086(3) -0.0041(4) C5A 0.0228(4) 0.0197(4) 0.0157(4) -0.0019(3) 0.0025(3) -0.0058(3) C6A 0.0385(6) 0.0435(7) 0.0160(4) -0.0015(4) 0.0041(4) -0.0150(6) O1B 0.0152(3) 0.0095(2) 0.0263(3) 0.0012(2) -0.0024(2) -0.0042(2) O2B 0.0133(3) 0.0153(3) 0.0216(3) -0.0009(2) 0.0010(2) -0.0072(2) N1B 0.0140(3) 0.0101(3) 0.0168(3) 0.0003(2) -0.0025(2) -0.0050(3) C1B 0.0132(3) 0.0100(3) 0.0117(3) -0.0013(2) 0.0013(2) -0.0044(3) C2B 0.0117(3) 0.0095(3) 0.0143(3) 0.0003(3) -0.0005(2) -0.0038(3) C3B 0.0178(4) 0.0176(4) 0.0143(3) 0.0019(3) 0.0013(3) -0.0069(3) C4B 0.0253(4) 0.0201(4) 0.0157(3) 0.0012(3) -0.0036(3) -0.0098(3) C5B 0.0487(8) 0.0374(6) 0.0171(4) -0.0049(4) -0.0016(4) -0.0048(6) C6B 0.0232(4) 0.0299(5) 0.0235(4) 0.0037(4) -0.0043(3) -0.0025(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 O1A C1A 1.2639(11) . ? O2A C1A 1.2634(11) . ? N1A C2A 1.4989(11) . ? N1A H1A 0.913(18) . ? N1A H2A 0.966(17) . ? N1A H3A 0.920(17) . ? C1A C2A 1.5461(11) . ? C2A C3A 1.5545(12) . ? C2A H21A 1.0000 . ? C3A C4A 1.5338(13) . ? C3A C5A 1.5393(13) . ? C3A H31A 1.0000 . ? C4A H41A 0.9800 . ? C4A H42A 0.9800 . ? C4A H43A 0.9800 . ? C5A C6A 1.5374(14) . ? C5A H51A 0.9900 . ? C5A H52A 0.9900 . ? C6A H61A 0.9800 . ? C6A H62A 0.9800 . ? C6A H63A 0.9800 . ? O1B C1B 1.2653(11) . ? O2B C1B 1.2630(11) . ? N1B C2B 1.5006(11) . ? N1B H1B 0.928(18) . ? N1B H2B 0.858(17) . ? N1B H3B 0.843(17) . ? C1B C2B 1.5495(12) . ? C2B C3B 1.5415(12) . ? C2B H21B 1.0000 . ? C3B C4B 1.5370(13) . ? C3B H31B 0.9900 . ? C3B H32B 0.9900 . ? C4B C6B 1.5357(15) . ? C4B C5B 1.5392(15) . ? C4B H41B 1.0000 . ? C5B H51B 0.9800 . ? C5B H52B 0.9800 . ? C5B H53B 0.9800 . ? C6B H61B 0.9800 . ? C6B H62B 0.9800 . ? C6B H63B 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 C2A N1A H1A 113.6(10) . . ? C2A N1A H2A 112.7(10) . . ? H1A N1A H2A 105.3(14) . . ? C2A N1A H3A 110.3(11) . . ? H1A N1A H3A 105.7(15) . . ? H2A N1A H3A 108.8(14) . . ? O2A C1A O1A 125.82(8) . . ? O2A C1A C2A 117.20(7) . . ? O1A C1A C2A 116.97(7) . . ? N1A C2A C1A 109.34(7) . . ? N1A C2A C3A 110.48(7) . . ? C1A C2A C3A 112.80(7) . . ? N1A C2A H21A 108.0 . . ? C1A C2A H21A 108.0 . . ? C3A C2A H21A 108.0 . . ? C4A C3A C5A 112.03(8) . . ? C4A C3A C2A 109.84(8) . . ? C5A C3A C2A 112.09(7) . . ? C4A C3A H31A 107.6 . . ? C5A C3A H31A 107.6 . . ? C2A C3A H31A 107.6 . . ? C3A C4A H41A 109.5 . . ? C3A C4A H42A 109.5 . . ? H41A C4A H42A 109.5 . . ? C3A C4A H43A 109.5 . . ? H41A C4A H43A 109.5 . . ? H42A C4A H43A 109.5 . . ? C6A C5A C3A 113.34(9) . . ? C6A C5A H51A 108.9 . . ? C3A C5A H51A 108.9 . . ? C6A C5A H52A 108.9 . . ? C3A C5A H52A 108.9 . . ? H51A C5A H52A 107.7 . . ? C5A C6A H61A 109.5 . . ? C5A C6A H62A 109.5 . . ? H61A C6A H62A 109.5 . . ? C5A C6A H63A 109.5 . . ? H61A C6A H63A 109.5 . . ? H62A C6A H63A 109.5 . . ? C2B N1B H1B 111.9(10) . . ? C2B N1B H2B 108.8(11) . . ? H1B N1B H2B 109.9(15) . . ? C2B N1B H3B 110.9(12) . . ? H1B N1B H3B 105.3(16) . . ? H2B N1B H3B 110.1(15) . . ? O2B C1B O1B 126.00(8) . . ? O2B C1B C2B 117.97(7) . . ? O1B C1B C2B 116.02(7) . . ? N1B C2B C3B 107.99(7) . . ? N1B C2B C1B 108.80(7) . . ? C3B C2B C1B 110.74(7) . . ? N1B C2B H21B 109.8 . . ? C3B C2B H21B 109.8 . . ? C1B C2B H21B 109.8 . . ? C4B C3B C2B 114.74(8) . . ? C4B C3B H31B 108.6 . . ? C2B C3B H31B 108.6 . . ? C4B C3B H32B 108.6 . . ? C2B C3B H32B 108.6 . . ? H31B C3B H32B 107.6 . . ? C6B C4B C3B 111.35(8) . . ? C6B C4B C5B 110.27(9) . . ? C3B C4B C5B 109.48(10) . . ? C6B C4B H41B 108.6 . . ? C3B C4B H41B 108.6 . . ? C5B C4B H41B 108.6 . . ? C4B C5B H51B 109.5 . . ? C4B C5B H52B 109.5 . . ? H51B C5B H52B 109.5 . . ? C4B C5B H53B 109.5 . . ? H51B C5B H53B 109.5 . . ? H52B C5B H53B 109.5 . . ? C4B C6B H61B 109.5 . . ? C4B C6B H62B 109.5 . . ? H61B C6B H62B 109.5 . . ? C4B C6B H63B 109.5 . . ? H61B C6B H63B 109.5 . . ? H62B C6B H63B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2A C1A C2A N1A 157.60(7) . . . . ? O1A C1A C2A N1A -22.83(10) . . . . ? O2A C1A C2A C3A -79.04(9) . . . . ? O1A C1A C2A C3A 100.52(9) . . . . ? N1A C2A C3A C4A -152.09(8) . . . . ? C1A C2A C3A C4A 85.20(9) . . . . ? N1A C2A C3A C5A 82.69(9) . . . . ? C1A C2A C3A C5A -40.03(10) . . . . ? C4A C3A C5A C6A 63.13(11) . . . . ? C2A C3A C5A C6A -172.86(9) . . . . ? O2B C1B C2B N1B -147.36(8) . . . . ? O1B C1B C2B N1B 33.82(10) . . . . ? O2B C1B C2B C3B 94.10(9) . . . . ? O1B C1B C2B C3B -84.73(9) . . . . ? N1B C2B C3B C4B 169.52(7) . . . . ? C1B C2B C3B C4B -71.45(10) . . . . ? C2B C3B C4B C6B -76.28(11) . . . . ? C2B C3B C4B C5B 161.52(9) . . . . ? 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 N1A H1A O2A 0.913(18) 1.974(18) 2.8734(10) 168.1(15) 1_655 N1A H2A O1A 0.966(17) 1.790(17) 2.7540(10) 175.0(15) 1_565 N1A H3A O2B 0.920(17) 2.093(17) 2.9532(10) 155.1(15) . N1B H1B O2B 0.928(18) 1.971(18) 2.8973(10) 176.0(15) 1_455 N1B H2B O1B 0.858(17) 1.882(17) 2.7365(10) 174.0(17) 1_545 N1B H3B O2A 0.843(17) 2.113(18) 2.9298(11) 163.4(16) . _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.331 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.070 data_II _database_code_depnum_ccdc_archive 'CCDC 772921' #TrackingRef 'C004055J.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; S-2-aminopentanoic acid : R-methionine (1:1) ; _chemical_name_common L-norvaline:D-methionine _chemical_melting_point ? _chemical_formula_moiety 'C5 H11 N O2, C5 H11 N O2 S' _chemical_formula_sum 'C10 H22 N2 O4 S' _chemical_formula_weight 266.36 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.89650(10) _cell_length_b 4.69630(10) _cell_length_c 16.11880(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.9890(10) _cell_angle_gamma 90.00 _cell_volume 716.460(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 49.82 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8000 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'Sets of exposures each taken over 0.3\% \w rotation' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 20822 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 49.82 _reflns_number_total 11256 _reflns_number_gt 8842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT+ (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement 'SHELXTL (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Data were collected by measuring six sets of exposures with the detector set at 2\q = 29\% and 65\%, crystal-to-detector distance 5.00 cm. Refinement of F^2^ against ALL reflections. ; _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^)+(0.0634P)^2^+0.0133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(4) _refine_ls_number_reflns 11256 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.91560(5) 0.21942(13) 0.43123(3) 0.01800(9) Uani 1 1 d . . . O2A O 0.72761(5) 0.49154(14) 0.36794(4) 0.02250(11) Uani 1 1 d . . . N1A N 1.09681(6) 0.60459(14) 0.40112(4) 0.01576(10) Uani 1 1 d . . . H1A H 1.1336(15) 0.447(4) 0.3983(9) 0.024 Uiso 1 1 d . . . H2A H 1.1454(14) 0.751(3) 0.3841(9) 0.024 Uiso 1 1 d . . . H3A H 1.0967(13) 0.625(3) 0.4542(8) 0.024 Uiso 1 1 d . . . C1A C 0.85698(6) 0.42587(14) 0.38585(4) 0.01385(10) Uani 1 1 d . . . C2A C 0.94775(6) 0.60913(15) 0.34410(4) 0.01459(10) Uani 1 1 d . . . H21A H 0.9118 0.8094 0.3382 0.018 Uiso 1 1 calc R . . C3A C 0.93800(8) 0.48938(19) 0.25387(4) 0.02047(13) Uani 1 1 d . . . H31A H 0.9684 0.2877 0.2603 0.025 Uiso 1 1 calc R . . H32A H 0.8378 0.4934 0.2182 0.025 Uiso 1 1 calc R . . C4A C 1.02592(16) 0.6473(3) 0.20526(7) 0.0466(3) Uani 1 1 d . . . H41A H 0.9922 0.8464 0.1955 0.056 Uiso 1 1 calc R . . H42A H 1.1256 0.6518 0.2418 0.056 Uiso 1 1 calc R . . C5A C 1.01921(17) 0.5134(4) 0.11872(7) 0.0501(3) Uani 1 1 d . . . H51A H 1.0746 0.6280 0.0896 0.075 Uiso 1 1 calc R . . H52A H 0.9207 0.5055 0.0825 0.075 Uiso 1 1 calc R . . H53A H 1.0580 0.3201 0.1281 0.075 Uiso 1 1 calc R . . S1B S 0.53616(3) 1.13864(8) 0.110554(16) 0.03970(7) Uani 1 1 d . . . O1B O 0.41687(5) 1.37620(13) 0.43153(3) 0.01734(9) Uani 1 1 d . . . O2B O 0.22934(5) 1.10166(13) 0.36894(4) 0.02174(11) Uani 1 1 d . . . N1B N 0.59909(5) 0.98990(14) 0.40350(4) 0.01544(9) Uani 1 1 d . . . H1B H 0.6406(14) 1.157(4) 0.3994(8) 0.023 Uiso 1 1 d . . . H2B H 0.6446(14) 0.847(3) 0.3881(9) 0.023 Uiso 1 1 d . . . H3B H 0.5972(14) 0.955(3) 0.4579(9) 0.023 Uiso 1 1 d . . . C1B C 0.35863(6) 1.16624(15) 0.38714(4) 0.01363(10) Uani 1 1 d . . . C2B C 0.45045(6) 0.98401(14) 0.34623(4) 0.01333(9) Uani 1 1 d . . . H21B H 0.4148 0.7836 0.3395 0.016 Uiso 1 1 calc R . . C3B C 0.44172(7) 1.10959(18) 0.25685(4) 0.01847(12) Uani 1 1 d . . . H31B H 0.3427 1.0971 0.2197 0.022 Uiso 1 1 calc R . . H32B H 0.4672 1.3138 0.2641 0.022 Uiso 1 1 calc R . . C4B C 0.53674(10) 0.9639(2) 0.21037(5) 0.02923(16) Uani 1 1 d . . . H41B H 0.5051 0.7645 0.1975 0.035 Uiso 1 1 calc R . . H42B H 0.6346 0.9597 0.2495 0.035 Uiso 1 1 calc R . . C5B C 0.35861(17) 1.0697(4) 0.04440(7) 0.0529(4) Uani 1 1 d . . . H51B H 0.3468 1.1401 -0.0145 0.079 Uiso 1 1 calc R . . H52B H 0.2918 1.1671 0.0692 0.079 Uiso 1 1 calc R . . H53B H 0.3406 0.8642 0.0425 0.079 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 O1A 0.0182(2) 0.0163(2) 0.0211(2) 0.00376(16) 0.00821(16) 0.00025(17) O2A 0.01150(17) 0.0186(3) 0.0391(3) 0.0010(2) 0.01016(18) 0.00170(19) N1A 0.01303(19) 0.0168(3) 0.0191(2) -0.00222(18) 0.00731(16) -0.00302(19) C1A 0.0117(2) 0.0125(3) 0.0190(2) -0.00116(18) 0.00699(17) -0.00022(18) C2A 0.0136(2) 0.0129(3) 0.0187(2) 0.0010(2) 0.00709(17) 0.0009(2) C3A 0.0213(3) 0.0235(4) 0.0171(2) -0.0001(2) 0.0063(2) -0.0007(3) C4A 0.0821(9) 0.0372(5) 0.0354(4) -0.0077(5) 0.0404(5) -0.0219(6) C5A 0.0633(7) 0.0688(9) 0.0257(4) -0.0057(5) 0.0249(5) -0.0097(7) S1B 0.05604(15) 0.04450(14) 0.02886(9) 0.00228(10) 0.02853(10) -0.00313(12) O1B 0.01768(19) 0.0161(2) 0.0194(2) -0.00390(16) 0.00721(16) -0.00100(17) O2B 0.01226(17) 0.0187(3) 0.0366(3) -0.0013(2) 0.01073(17) -0.00049(19) N1B 0.01211(19) 0.0163(3) 0.0193(2) 0.00265(18) 0.00665(16) 0.00258(19) C1B 0.0120(2) 0.0135(3) 0.0171(2) 0.00141(18) 0.00690(16) 0.00048(19) C2B 0.0126(2) 0.0121(3) 0.0167(2) 0.00006(18) 0.00656(16) 0.0004(2) C3B 0.0212(3) 0.0195(3) 0.0165(2) 0.0010(2) 0.00825(19) 0.0028(3) C4B 0.0376(4) 0.0313(4) 0.0260(3) 0.0030(3) 0.0207(3) 0.0075(4) C5B 0.0631(8) 0.0748(11) 0.0232(4) -0.0006(5) 0.0162(4) 0.0072(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.2504(9) . ? O2A C1A 1.2655(8) . ? N1A C2A 1.4930(8) . ? N1A H1A 0.832(17) . ? N1A H2A 0.924(15) . ? N1A H3A 0.862(13) . ? C1A C2A 1.5343(9) . ? C2A C3A 1.5358(9) . ? C2A H21A 1.0000 . ? C3A C4A 1.5230(12) . ? C3A H31A 0.9900 . ? C3A H32A 0.9900 . ? C4A C5A 1.5136(15) . ? C4A H41A 0.9900 . ? C4A H42A 0.9900 . ? C5A H51A 0.9800 . ? C5A H52A 0.9800 . ? C5A H53A 0.9800 . ? S1B C5B 1.7985(16) . ? S1B C4B 1.8047(9) . ? O1B C1B 1.2552(9) . ? O2B C1B 1.2633(7) . ? N1B C2B 1.4911(8) . ? N1B H1B 0.897(16) . ? N1B H2B 0.883(15) . ? N1B H3B 0.898(14) . ? C1B C2B 1.5308(8) . ? C2B C3B 1.5355(9) . ? C2B H21B 1.0000 . ? C3B C4B 1.5250(10) . ? C3B H31B 0.9900 . ? C3B H32B 0.9900 . ? C4B H41B 0.9900 . ? C4B H42B 0.9900 . ? C5B H51B 0.9800 . ? C5B H52B 0.9800 . ? C5B H53B 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 C2A N1A H1A 110.4(10) . . ? C2A N1A H2A 108.3(8) . . ? H1A N1A H2A 111.7(13) . . ? C2A N1A H3A 108.8(8) . . ? H1A N1A H3A 106.4(13) . . ? H2A N1A H3A 111.2(13) . . ? O1A C1A O2A 126.01(6) . . ? O1A C1A C2A 117.42(5) . . ? O2A C1A C2A 116.50(6) . . ? N1A C2A C1A 108.77(5) . . ? N1A C2A C3A 110.80(5) . . ? C1A C2A C3A 109.10(6) . . ? N1A C2A H21A 109.4 . . ? C1A C2A H21A 109.4 . . ? C3A C2A H21A 109.4 . . ? C4A C3A C2A 114.94(7) . . ? C4A C3A H31A 108.5 . . ? C2A C3A H31A 108.5 . . ? C4A C3A H32A 108.5 . . ? C2A C3A H32A 108.5 . . ? H31A C3A H32A 107.5 . . ? C5A C4A C3A 113.21(10) . . ? C5A C4A H41A 108.9 . . ? C3A C4A H41A 108.9 . . ? C5A C4A H42A 108.9 . . ? C3A C4A H42A 108.9 . . ? H41A C4A H42A 107.7 . . ? C4A C5A H51A 109.5 . . ? C4A C5A H52A 109.5 . . ? H51A C5A H52A 109.5 . . ? C4A C5A H53A 109.5 . . ? H51A C5A H53A 109.5 . . ? H52A C5A H53A 109.5 . . ? C5B S1B C4B 101.23(6) . . ? C2B N1B H1B 111.1(8) . . ? C2B N1B H2B 107.7(9) . . ? H1B N1B H2B 111.2(12) . . ? C2B N1B H3B 107.7(8) . . ? H1B N1B H3B 111.8(12) . . ? H2B N1B H3B 107.2(12) . . ? O1B C1B O2B 125.88(6) . . ? O1B C1B C2B 116.96(5) . . ? O2B C1B C2B 117.02(6) . . ? N1B C2B C1B 108.98(5) . . ? N1B C2B C3B 110.41(5) . . ? C1B C2B C3B 108.16(5) . . ? N1B C2B H21B 109.8 . . ? C1B C2B H21B 109.8 . . ? C3B C2B H21B 109.8 . . ? C4B C3B C2B 114.51(6) . . ? C4B C3B H31B 108.6 . . ? C2B C3B H31B 108.6 . . ? C4B C3B H32B 108.6 . . ? C2B C3B H32B 108.6 . . ? H31B C3B H32B 107.6 . . ? C3B C4B S1B 113.09(6) . . ? C3B C4B H41B 109.0 . . ? S1B C4B H41B 109.0 . . ? C3B C4B H42B 109.0 . . ? S1B C4B H42B 109.0 . . ? H41B C4B H42B 107.8 . . ? S1B C5B H51B 109.5 . . ? S1B C5B H52B 109.5 . . ? H51B C5B H52B 109.5 . . ? S1B C5B H53B 109.5 . . ? H51B C5B H53B 109.5 . . ? H52B C5B H53B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A C2A N1A -30.33(8) . . . . ? O2A C1A C2A N1A 152.57(6) . . . . ? O1A C1A C2A C3A 90.64(7) . . . . ? O2A C1A C2A C3A -86.46(8) . . . . ? N1A C2A C3A C4A -59.02(11) . . . . ? C1A C2A C3A C4A -178.74(9) . . . . ? C2A C3A C4A C5A 177.04(11) . . . . ? O1B C1B C2B N1B 31.25(8) . . . . ? O2B C1B C2B N1B -152.84(6) . . . . ? O1B C1B C2B C3B -88.82(7) . . . . ? O2B C1B C2B C3B 87.10(7) . . . . ? N1B C2B C3B C4B 56.51(9) . . . . ? C1B C2B C3B C4B 175.68(7) . . . . ? C2B C3B C4B S1B -174.42(6) . . . . ? C5B S1B C4B C3B -67.85(9) . . . . ? 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 N1A H1A O2B 0.832(17) 2.004(17) 2.8223(9) 168.0(14) 1_645 N1A H2A O2B 0.924(15) 1.893(15) 2.7993(8) 166.1(13) 1_655 N1A H3A O1A 0.862(13) 1.937(13) 2.7934(7) 172.4(14) 2_756 N1B H1B O2A 0.897(16) 1.930(16) 2.8147(9) 168.8(12) 1_565 N1B H2B O2A 0.883(15) 1.930(15) 2.8019(8) 169.0(14) . N1B H3B O1B 0.898(14) 1.865(14) 2.7615(7) 176.8(13) 2_646 _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 43.10 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.547 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.059 data_III _database_code_depnum_ccdc_archive 'CCDC 772922' #TrackingRef 'C004055J.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; S-2-aminobutanoic acid : R-2-aminohexanoic acid (1:1) ; _chemical_name_common 'L-aminobutyric acid:D-norleucine' _chemical_melting_point ? _chemical_formula_moiety 'C4 H9 N O2, C6 H13 N O2' _chemical_formula_sum 'C10 H22 N2 O4' _chemical_formula_weight 234.30 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.1725(3) _cell_length_b 5.3955(3) _cell_length_c 12.3952(7) _cell_angle_alpha 92.631(2) _cell_angle_beta 94.747(2) _cell_angle_gamma 113.103(2) _cell_volume 315.93(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 36.31 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 128 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8000 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'Sets of exposures each taken over 0.3\% \w rotation' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5342 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 36.31 _reflns_number_total 3647 _reflns_number_gt 2946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT+ (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement 'SHELXTL (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Data were collected by measuring six sets of exposures with the detector set at 2\q = 29\% and 65\%, crystal-to-detector distance 5.00 cm. Refinement of F^2^ against ALL reflections. ; _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^)+(0.0484P)^2^+0.1313P] 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 3647 _refine_ls_number_parameters 164 _refine_ls_number_restraints 56 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 O1A O 0.7772(4) 0.7010(5) 0.7144(2) 0.0215(6) Uani 1 1 d . . . O2A O 0.3159(4) 0.5632(5) 0.7327(2) 0.0188(5) Uani 1 1 d . . . N1A N 0.7456(5) 0.1906(5) 0.6912(2) 0.0146(5) Uani 1 1 d U . . H1A H 0.9187 0.3250 0.7118 0.022 Uiso 1 1 calc R . . H2A H 0.7015 0.1866 0.6184 0.022 Uiso 1 1 calc R . . H3A H 0.7488 0.0290 0.7075 0.022 Uiso 1 1 calc R . . C1A C 0.5373(6) 0.5247(6) 0.7304(3) 0.0166(7) Uani 1 1 d . . . C2A C 0.5269(6) 0.2423(7) 0.7507(3) 0.0170(6) Uani 1 1 d U . . H21A H 0.3357 0.1046 0.7216 0.020 Uiso 1 1 calc R . . C3A C 0.5798(7) 0.2086(7) 0.8708(3) 0.0223(8) Uani 1 1 d . . . H31A H 0.7538 0.3620 0.9031 0.027 Uiso 1 1 calc R . . H32A H 0.6113 0.0403 0.8781 0.027 Uiso 1 1 calc R . . C4A C 0.3344(9) 0.1966(11) 0.9336(4) 0.0391(12) Uani 1 1 d . . . H41A H 0.3760 0.1701 1.0098 0.059 Uiso 1 1 calc R . . H42A H 0.1613 0.0456 0.9018 0.059 Uiso 1 1 calc R . . H43A H 0.3081 0.3664 0.9296 0.059 Uiso 1 1 calc R . . O1B O 0.0675(4) 0.1728(4) 0.50245(19) 0.0196(5) Uani 0.794(5) 1 d PD A 1 O2B O 0.5266(4) 0.3104(5) 0.4821(2) 0.0196(5) Uani 0.794(5) 1 d PD A 1 N1B N 0.0977(5) 0.6785(5) 0.5240(2) 0.0159(6) Uani 0.794(5) 1 d PD A 1 H1B H -0.0754 0.5663 0.4908 0.024 Uiso 0.794(5) 1 calc PR A 1 H2B H 0.1181 0.8533 0.5210 0.024 Uiso 0.794(5) 1 calc PR A 1 H3B H 0.1135 0.6422 0.5946 0.024 Uiso 0.794(5) 1 calc PR A 1 C1B C 0.3012(5) 0.3478(6) 0.4853(2) 0.0115(6) Uani 0.794(5) 1 d PDU A 1 C2B C 0.3181(7) 0.6360(6) 0.4685(3) 0.0115(6) Uani 0.794(5) 1 d PDU A 1 H21B H 0.5075 0.7715 0.5007 0.017 Uiso 0.794(5) 1 calc PR A 1 C3B C 0.2772(8) 0.6715(8) 0.3464(3) 0.0174(9) Uani 0.794(5) 1 d PD A 1 H31B H 0.1119 0.5132 0.3115 0.021 Uiso 0.794(5) 1 calc PR A 1 H32B H 0.2356 0.8341 0.3379 0.021 Uiso 0.794(5) 1 calc PR A 1 C4B C 0.5343(9) 0.7004(10) 0.2885(3) 0.0234(10) Uani 0.794(5) 1 d PD A 1 H41B H 0.7049 0.8416 0.3295 0.028 Uiso 0.794(5) 1 calc PR A 1 H42B H 0.5594 0.5276 0.2874 0.028 Uiso 0.794(5) 1 calc PR A 1 C5B C 0.5073(8) 0.7749(9) 0.1730(3) 0.0410(9) Uani 0.794(5) 1 d PDU A 1 H51B H 0.4754 0.9442 0.1739 0.049 Uiso 0.794(5) 1 calc PR A 1 H52B H 0.3405 0.6305 0.1313 0.049 Uiso 0.794(5) 1 calc PR A 1 C6B C 0.7687(10) 0.8134(13) 0.1162(4) 0.0563(13) Uani 0.794(5) 1 d PDU A 1 H61B H 0.9289 0.9734 0.1507 0.085 Uiso 0.794(5) 1 calc PR A 1 H62B H 0.7324 0.8382 0.0394 0.085 Uiso 0.794(5) 1 calc PR A 1 H63B H 0.8132 0.6535 0.1219 0.085 Uiso 0.794(5) 1 calc PR A 1 O12B O 0.0675(4) 0.1728(4) 0.50245(19) 0.0196(5) Uani 0.206(5) 1 d PD A 2 O22B O 0.5266(4) 0.3104(5) 0.4821(2) 0.0196(5) Uani 0.206(5) 1 d PD A 2 N12B N 0.0977(5) 0.6785(5) 0.5240(2) 0.0159(6) Uani 0.206(5) 1 d PD A 2 H4B H -0.0823 0.5563 0.5040 0.024 Uiso 0.206(5) 1 calc PR A 2 H5B H 0.1071 0.8483 0.5154 0.024 Uiso 0.206(5) 1 calc PR A 2 H6B H 0.1486 0.6657 0.5949 0.024 Uiso 0.206(5) 1 calc PR A 2 C12B C 0.3012(5) 0.3478(6) 0.4853(2) 0.0115(6) Uani 0.206(5) 1 d PD A 2 C22B C 0.2936(16) 0.6215(12) 0.4548(5) 0.0115(6) Uani 0.206(5) 1 d PD A 2 H22B H 0.4872 0.7685 0.4701 0.017 Uiso 0.206(5) 1 calc PR A 2 C32B C 0.184(2) 0.607(2) 0.3343(5) 0.017 Uiso 0.206(5) 1 d PD A 2 H33B H 0.0108 0.4388 0.3175 0.020 Uiso 0.206(5) 1 calc PR A 2 H34B H 0.1291 0.7610 0.3239 0.020 Uiso 0.206(5) 1 calc PR A 2 C42B C 0.389(2) 0.6103(18) 0.2529(7) 0.022 Uiso 0.206(5) 1 d PD A 2 H43B H 0.4825 0.4884 0.2744 0.026 Uiso 0.206(5) 1 calc PR A 2 H44B H 0.2817 0.5390 0.1805 0.026 Uiso 0.206(5) 1 calc PR A 2 C52B C 0.614(2) 0.889(2) 0.2444(11) 0.039 Uiso 0.206(5) 1 d PD A 2 H53B H 0.7448 0.9437 0.3122 0.047 Uiso 0.206(5) 1 calc PR A 2 H54B H 0.5214 1.0182 0.2385 0.047 Uiso 0.206(5) 1 calc PR A 2 C62B C 0.784(4) 0.909(3) 0.1485(16) 0.056 Uiso 0.206(5) 1 d PD A 2 H64B H 0.9312 1.0927 0.1509 0.084 Uiso 0.206(5) 1 calc PR A 2 H65B H 0.6589 0.8699 0.0806 0.084 Uiso 0.206(5) 1 calc PR A 2 H66B H 0.8728 0.7789 0.1523 0.084 Uiso 0.206(5) 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 O1A 0.0156(11) 0.0113(11) 0.0401(16) 0.0056(11) 0.0087(10) 0.0066(9) O2A 0.0155(10) 0.0146(11) 0.0292(13) 0.0016(10) 0.0037(9) 0.0089(9) N1A 0.0144(10) 0.0099(11) 0.0216(12) 0.0022(10) 0.0051(9) 0.0064(8) C1A 0.0159(13) 0.0113(13) 0.0211(15) 0.0025(12) 0.0023(11) 0.0037(10) C2A 0.0128(11) 0.0143(12) 0.0237(13) 0.0000(10) 0.0049(9) 0.0048(9) C3A 0.0280(17) 0.0231(19) 0.0258(19) 0.0075(15) 0.0093(14) 0.0189(15) C4A 0.037(2) 0.058(3) 0.032(2) 0.012(2) 0.0154(18) 0.026(2) O1B 0.0177(11) 0.0105(11) 0.0313(14) 0.0042(10) 0.0068(10) 0.0053(9) O2B 0.0152(10) 0.0144(11) 0.0308(14) 0.0019(10) 0.0023(9) 0.0076(9) N1B 0.0168(11) 0.0092(11) 0.0231(13) 0.0030(10) 0.0055(9) 0.0058(9) C1B 0.0127(11) 0.0085(11) 0.0154(12) -0.0010(10) 0.0005(9) 0.0068(9) C2B 0.0116(11) 0.0053(10) 0.0193(12) 0.0037(9) 0.0029(9) 0.0047(8) C3B 0.0151(17) 0.018(2) 0.019(2) 0.0054(16) 0.0023(14) 0.0052(15) C4B 0.0229(18) 0.037(2) 0.018(2) 0.0110(17) 0.0073(14) 0.0178(16) C5B 0.0342(17) 0.071(2) 0.0284(17) 0.0209(17) 0.0125(13) 0.0292(17) C6B 0.049(2) 0.097(3) 0.037(2) 0.031(2) 0.0216(18) 0.039(2) O12B 0.0177(11) 0.0105(11) 0.0313(14) 0.0042(10) 0.0068(10) 0.0053(9) O22B 0.0152(10) 0.0144(11) 0.0308(14) 0.0019(10) 0.0023(9) 0.0076(9) N12B 0.0168(11) 0.0092(11) 0.0231(13) 0.0030(10) 0.0055(9) 0.0058(9) C12B 0.0127(11) 0.0085(11) 0.0154(12) -0.0010(10) 0.0005(9) 0.0068(9) C22B 0.0116(11) 0.0053(10) 0.0193(12) 0.0037(9) 0.0029(9) 0.0047(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.271(4) . ? O2A C1A 1.244(4) . ? N1A C2A 1.506(5) . ? N1A H1A 0.9100 . ? N1A H2A 0.9100 . ? N1A H3A 0.9100 . ? C1A C2A 1.536(5) . ? C2A C3A 1.523(5) . ? C2A H21A 1.0000 . ? C3A C4A 1.525(6) . ? C3A H31A 0.9900 . ? C3A H32A 0.9900 . ? C4A H41A 0.9800 . ? C4A H42A 0.9800 . ? C4A H43A 0.9800 . ? O1B C1B 1.250(4) . ? O2B C1B 1.262(4) . ? N1B C2B 1.465(5) . ? N1B H1B 0.9100 . ? N1B H2B 0.9100 . ? N1B H3B 0.9100 . ? C1B C2B 1.548(4) . ? C2B C3B 1.541(5) . ? C2B H21B 1.0000 . ? C3B C4B 1.521(6) . ? C3B H31B 0.9900 . ? C3B H32B 0.9900 . ? C4B C5B 1.515(5) . ? C4B H41B 0.9900 . ? C4B H42B 0.9900 . ? C5B C6B 1.523(5) . ? C5B H51B 0.9900 . ? C5B H52B 0.9900 . ? C6B H61B 0.9800 . ? C6B H62B 0.9800 . ? C6B H63B 0.9800 . ? C22B C32B 1.539(6) . ? C22B H22B 1.0000 . ? C32B C42B 1.520(7) . ? C32B H33B 0.9900 . ? C32B H34B 0.9900 . ? C42B C52B 1.510(7) . ? C42B H43B 0.9900 . ? C42B H44B 0.9900 . ? C52B C62B 1.521(7) . ? C52B H53B 0.9900 . ? C52B H54B 0.9900 . ? C62B H64B 0.9800 . ? C62B H65B 0.9800 . ? C62B H66B 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 C2A N1A H1A 109.5 . . ? C2A N1A H2A 109.5 . . ? H1A N1A H2A 109.5 . . ? C2A N1A H3A 109.5 . . ? H1A N1A H3A 109.5 . . ? H2A N1A H3A 109.5 . . ? O2A C1A O1A 125.7(3) . . ? O2A C1A C2A 118.3(3) . . ? O1A C1A C2A 116.0(3) . . ? N1A C2A C3A 108.7(3) . . ? N1A C2A C1A 109.6(2) . . ? C3A C2A C1A 112.7(3) . . ? N1A C2A H21A 108.6 . . ? C3A C2A H21A 108.6 . . ? C1A C2A H21A 108.6 . . ? C2A C3A C4A 112.5(3) . . ? C2A C3A H31A 109.1 . . ? C4A C3A H31A 109.1 . . ? C2A C3A H32A 109.1 . . ? C4A C3A H32A 109.1 . . ? H31A C3A H32A 107.8 . . ? C3A C4A H41A 109.5 . . ? C3A C4A H42A 109.5 . . ? H41A C4A H42A 109.5 . . ? C3A C4A H43A 109.5 . . ? H41A C4A H43A 109.5 . . ? H42A C4A H43A 109.5 . . ? O1B C1B O2B 125.5(3) . . ? O1B C1B C2B 117.5(2) . . ? O2B C1B C2B 117.0(3) . . ? N1B C2B C3B 110.0(3) . . ? N1B C2B C1B 108.8(2) . . ? C3B C2B C1B 110.4(3) . . ? N1B C2B H21B 109.2 . . ? C3B C2B H21B 109.2 . . ? C1B C2B H21B 109.2 . . ? C4B C3B C2B 113.1(3) . . ? C4B C3B H31B 109.0 . . ? C2B C3B H31B 109.0 . . ? C4B C3B H32B 109.0 . . ? C2B C3B H32B 109.0 . . ? H31B C3B H32B 107.8 . . ? C5B C4B C3B 112.4(3) . . ? C5B C4B H41B 109.1 . . ? C3B C4B H41B 109.1 . . ? C5B C4B H42B 109.1 . . ? C3B C4B H42B 109.1 . . ? H41B C4B H42B 107.9 . . ? C4B C5B C6B 112.4(3) . . ? C4B C5B H51B 109.1 . . ? C6B C5B H51B 109.1 . . ? C4B C5B H52B 109.1 . . ? C6B C5B H52B 109.1 . . ? H51B C5B H52B 107.9 . . ? C5B C6B H61B 109.5 . . ? C5B C6B H62B 109.5 . . ? H61B C6B H62B 109.5 . . ? C5B C6B H63B 109.5 . . ? H61B C6B H63B 109.5 . . ? H62B C6B H63B 109.5 . . ? C32B C22B H22B 109.7 . . ? C42B C32B C22B 115.9(6) . . ? C42B C32B H33B 108.3 . . ? C22B C32B H33B 108.3 . . ? C42B C32B H34B 108.3 . . ? C22B C32B H34B 108.3 . . ? H33B C32B H34B 107.4 . . ? C52B C42B C32B 113.4(6) . . ? C52B C42B H43B 108.9 . . ? C32B C42B H43B 108.9 . . ? C52B C42B H44B 108.9 . . ? C32B C42B H44B 108.9 . . ? H43B C42B H44B 107.7 . . ? C42B C52B C62B 114.5(7) . . ? C42B C52B H53B 108.6 . . ? C62B C52B H53B 108.6 . . ? C42B C52B H54B 108.6 . . ? C62B C52B H54B 108.6 . . ? H53B C52B H54B 107.6 . . ? C52B C62B H64B 109.5 . . ? C52B C62B H65B 109.5 . . ? H64B C62B H65B 109.5 . . ? C52B C62B H66B 109.5 . . ? H64B C62B H66B 109.5 . . ? H65B C62B H66B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2A C1A C2A N1A 151.0(3) . . . . ? O1A C1A C2A N1A -30.1(4) . . . . ? O2A C1A C2A C3A -87.8(4) . . . . ? O1A C1A C2A C3A 91.1(3) . . . . ? N1A C2A C3A C4A -167.6(4) . . . . ? C1A C2A C3A C4A 70.7(4) . . . . ? O1B C1B C2B N1B 25.8(4) . . . . ? O2B C1B C2B N1B -153.1(3) . . . . ? O1B C1B C2B C3B -95.0(3) . . . . ? O2B C1B C2B C3B 86.1(4) . . . . ? N1B C2B C3B C4B 165.6(4) . . . . ? C1B C2B C3B C4B -74.3(4) . . . . ? C2B C3B C4B C5B -171.8(4) . . . . ? C3B C4B C5B C6B 178.0(5) . . . . ? C22B C32B C42B C52B -77.6(12) . . . . ? C32B C42B C52B C62B -168.3(13) . . . . ? 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 N1A H1A O2A 0.91 1.94 2.830(3) 166.7 1_655 N1A H3A O1A 0.91 1.84 2.736(4) 169.0 1_545 N1A H2A O2B 0.91 2.11 2.943(4) 152.2 . N1B H1B O2B 0.91 1.97 2.826(3) 156.4 1_455 N1B H2B O1B 0.91 1.86 2.756(4) 166.1 1_565 N1B H3B O2A 0.91 2.08 2.927(4) 154.4 . _diffrn_measured_fraction_theta_max 0.825 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.334 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.063