Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Carl Henrik Gorbitz' _publ_contact_author_address ; Department of Chemistry University of Oslo PO Box 1033 Blindern Oslo NO-0315 NORWAY ; _publ_contact_author_email C.H.GORBITZ@KJEMI.UIO.NO _publ_section_title ; Monoclinic nanoporous crystal structures for L-valyl-L-alanine acetonitrile solvate hydrate and L-valyl-L-serine trifluoroethanol solvate ; _publ_author_name 'Carl Gorbitz' #_vrf_PLAT773_VS-tfe20 #; #PROBLEM: Suspect C-C Bond in CIF: C1D -C2D .. 1.76 Ang. #RESPONSE: These are distances associated with low occupancy positions #for disordered solvent molecules and do not represent covalent bonds. #; # end Validation Reply Form data_VA-aw _database_code_depnum_ccdc_archive 'CCDC 283665' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Valyl-L-alanine acetonitrile solvate 0.85 hydrate ; _chemical_name_common 'L-Valyl-L-alanine acetonitrile solvate 0.85 hydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8.67 H17.57 N2.33 O3.29' _chemical_formula_weight 207.08 _chemical_absolute_configuration 'known for the purchased material' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.7281(5) _cell_length_b 10.1400(4) _cell_length_c 13.8928(6) _cell_angle_alpha 90.00 _cell_angle_beta 118.5780(10) _cell_angle_gamma 90.00 _cell_volume 1698.30(12) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 5245 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 35.00 _exptl_crystal_description 'Thick needle' _exptl_crystal_colour Colourless _exptl_crystal_size_max 1.200 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 673 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8215 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 105(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_% none _diffrn_reflns_number 22766 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 35.00 _reflns_number_total 7755 _reflns_number_gt 7002 _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 ; 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^)+(0.0588P)^2^+0.0761P] 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 7755 _refine_ls_number_parameters 457 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.004 _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 0.64885(9) 0.46825(11) 0.81543(8) 0.02321(19) Uani 1 1 d . . . O2A O 0.44885(11) 0.36250(12) 0.43541(9) 0.0301(2) Uani 1 1 d . . . O3A O 0.44974(8) 0.18561(10) 0.53118(7) 0.01990(17) Uani 1 1 d . . . N1A N 0.77978(8) 0.67395(11) 0.84965(8) 0.01372(16) Uani 1 1 d . . . H1A H 0.7288(17) 0.709(2) 0.8662(17) 0.021 Uiso 1 1 d . . . H2A H 0.8304(17) 0.731(2) 0.8602(17) 0.021 Uiso 1 1 d . . . H3A H 0.8176(17) 0.604(2) 0.8900(17) 0.021 Uiso 1 1 d . . . N2A N 0.54536(9) 0.50350(11) 0.63120(8) 0.01749(18) Uani 1 1 d . . . H4A H 0.5376(17) 0.552(2) 0.5800(17) 0.021 Uiso 1 1 d . . . C1A C 0.71136(9) 0.63271(12) 0.73286(9) 0.01375(17) Uani 1 1 d . . . H11A H 0.6674 0.7104 0.6895 0.016 Uiso 1 1 calc R . . C2A C 0.78293(11) 0.58225(14) 0.68207(10) 0.0199(2) Uani 1 1 d . . . H21A H 0.7310 0.5428 0.6093 0.024 Uiso 1 1 calc R . . C3A C 0.86433(17) 0.47354(19) 0.75005(16) 0.0375(4) Uani 1 1 d . . . H31A H 0.9022 0.4397 0.7106 0.056 Uiso 1 1 calc R . . H32A H 0.8237 0.4017 0.7621 0.056 Uiso 1 1 calc R . . H33A H 0.9192 0.5097 0.8208 0.056 Uiso 1 1 calc R . . C4A C 0.84307(12) 0.69557(17) 0.66040(12) 0.0260(3) Uani 1 1 d . . . H41A H 0.8886 0.6606 0.6293 0.039 Uiso 1 1 calc R . . H42A H 0.8907 0.7412 0.7294 0.039 Uiso 1 1 calc R . . H43A H 0.7885 0.7577 0.6086 0.039 Uiso 1 1 calc R . . C5A C 0.63097(9) 0.52713(12) 0.73030(9) 0.01485(18) Uani 1 1 d . . . C6A C 0.46478(10) 0.39886(13) 0.61181(9) 0.0168(2) Uani 1 1 d . . . H61A H 0.4905 0.3456 0.6803 0.020 Uiso 1 1 calc R . . C7A C 0.35049(12) 0.45653(16) 0.58045(13) 0.0252(3) Uani 1 1 d . . . H71A H 0.3555 0.5126 0.6401 0.038 Uiso 1 1 calc R . . H72A H 0.2979 0.3847 0.5676 0.038 Uiso 1 1 calc R . . H73A H 0.3248 0.5092 0.5135 0.038 Uiso 1 1 calc R . . C8A C 0.45544(9) 0.30819(13) 0.51884(9) 0.01505(18) Uani 1 1 d . . . O1B O 0.67163(7) 0.15793(10) -0.10907(8) 0.01707(16) Uani 1 1 d . . . O2B O 1.04676(7) 0.03687(11) -0.01899(8) 0.02025(17) Uani 1 1 d . . . O3B O 0.95580(7) -0.15433(10) -0.08068(8) 0.01813(16) Uani 1 1 d . . . N1B N 0.67044(8) 0.36147(11) 0.00524(8) 0.01266(15) Uani 1 1 d . . . H1B H 0.6349(16) 0.381(2) -0.0671(16) 0.019 Uiso 1 1 d . . . H2B H 0.6738(16) 0.438(2) 0.0399(16) 0.019 Uiso 1 1 d . . . H3B H 0.6310(16) 0.298(2) 0.0155(17) 0.019 Uiso 1 1 d . . . N2B N 0.85630(8) 0.15871(11) -0.05349(9) 0.01493(17) Uani 1 1 d . . . H4B H 0.9168(16) 0.194(2) -0.0188(16) 0.018 Uiso 1 1 d . . . C1B C 0.78358(8) 0.31372(11) 0.03055(9) 0.01158(16) Uani 1 1 d . . . H11B H 0.8237 0.3877 0.0171 0.014 Uiso 1 1 calc R . . C2B C 0.85309(9) 0.26787(12) 0.15018(9) 0.01503(19) Uani 1 1 d . . . H21B H 0.9223 0.2278 0.1562 0.018 Uiso 1 1 calc R . . C3B C 0.79543(12) 0.16010(15) 0.18116(11) 0.0228(2) Uani 1 1 d . . . H31B H 0.8456 0.1283 0.2553 0.034 Uiso 1 1 calc R . . H32B H 0.7756 0.0868 0.1291 0.034 Uiso 1 1 calc R . . H33B H 0.7281 0.1960 0.1789 0.034 Uiso 1 1 calc R . . C4B C 0.88944(10) 0.38446(14) 0.22987(10) 0.0197(2) Uani 1 1 d . . . H41B H 0.9352 0.3523 0.3049 0.029 Uiso 1 1 calc R . . H42B H 0.8238 0.4293 0.2245 0.029 Uiso 1 1 calc R . . H43B H 0.9326 0.4465 0.2112 0.029 Uiso 1 1 calc R . . C5B C 0.76598(8) 0.20362(12) -0.05117(9) 0.01232(17) Uani 1 1 d . . . C6B C 0.84912(9) 0.04363(12) -0.11993(9) 0.01456(18) Uani 1 1 d . . . H61B H 0.7900 -0.0164 -0.1228 0.017 Uiso 1 1 calc R . . C7B C 0.81980(12) 0.08253(16) -0.23772(11) 0.0239(2) Uani 1 1 d . . . H71B H 0.7503 0.1327 -0.2708 0.036 Uiso 1 1 calc R . . H72B H 0.8109 0.0028 -0.2810 0.036 Uiso 1 1 calc R . . H73B H 0.8794 0.1369 -0.2364 0.036 Uiso 1 1 calc R . . C8B C 0.96006(9) -0.03117(12) -0.06731(9) 0.01388(18) Uani 1 1 d . . . O1C O 0.39183(8) 0.32142(11) 0.15036(8) 0.01877(16) Uani 1 1 d . . . O2C O 0.50236(8) 0.16783(10) 0.00962(8) 0.01764(16) Uani 1 1 d . . . O3C O 0.32252(8) 0.11050(10) -0.08449(8) 0.01972(17) Uani 1 1 d . . . N1C N 0.47394(8) 0.52631(11) 0.29223(8) 0.01302(15) Uani 1 1 d . . . H1C H 0.4070(17) 0.560(2) 0.2447(17) 0.020 Uiso 1 1 d . . . H2C H 0.5097(16) 0.579(2) 0.3506(16) 0.020 Uiso 1 1 d . . . H3C H 0.4622(16) 0.454(2) 0.3203(17) 0.020 Uiso 1 1 d . . . N2C N 0.44166(8) 0.42064(10) 0.03321(8) 0.01257(15) Uani 1 1 d . . . H4C H 0.4666(15) 0.492(2) 0.0259(15) 0.015 Uiso 1 1 d . . . C1C C 0.52579(9) 0.49656(12) 0.22182(9) 0.01254(17) Uani 1 1 d . . . H11C H 0.5322 0.5807 0.1877 0.015 Uiso 1 1 calc R . . C2C C 0.64230(10) 0.43604(13) 0.28711(10) 0.0183(2) Uani 1 1 d . . . H21C H 0.6682 0.4146 0.2328 0.022 Uiso 1 1 calc R . . C3C C 0.64397(14) 0.3073(2) 0.3444(2) 0.0414(4) Uani 1 1 d . . . H31C H 0.7183 0.2685 0.3764 0.062 Uiso 1 1 calc R . . H32C H 0.5901 0.2458 0.2911 0.062 Uiso 1 1 calc R . . H33C H 0.6246 0.3248 0.4025 0.062 Uiso 1 1 calc R . . C4C C 0.72422(11) 0.53674(18) 0.36662(12) 0.0284(3) Uani 1 1 d . . . H41C H 0.7985 0.4977 0.4042 0.043 Uiso 1 1 calc R . . H42C H 0.7011 0.5621 0.4208 0.043 Uiso 1 1 calc R . . H43C H 0.7255 0.6150 0.3258 0.043 Uiso 1 1 calc R . . C5C C 0.44578(9) 0.40516(12) 0.13085(9) 0.01263(17) Uani 1 1 d . . . C6C C 0.36595(9) 0.33961(11) -0.05888(9) 0.01230(17) Uani 1 1 d . . . H61C H 0.2892 0.3487 -0.0686 0.015 Uiso 1 1 calc R . . C7C C 0.36663(10) 0.38435(13) -0.16416(9) 0.0175(2) Uani 1 1 d . . . H71C H 0.3580 0.4804 -0.1712 0.026 Uiso 1 1 calc R . . H72C H 0.3052 0.3421 -0.2276 0.026 Uiso 1 1 calc R . . H73C H 0.4371 0.3592 -0.1608 0.026 Uiso 1 1 calc R . . C8C C 0.40020(9) 0.19371(11) -0.04038(9) 0.01293(17) Uani 1 1 d . . . N1D N 1.0519(7) 0.4244(8) 0.5508(5) 0.115(3) Uani 0.883(6) 1 d PD A 1 C1D C 1.0210(3) 0.3315(5) 0.5715(3) 0.0664(10) Uani 0.883(6) 1 d PD A 1 C2D C 0.9813(4) 0.2093(4) 0.5947(3) 0.0702(10) Uani 0.883(6) 1 d PD A 1 H21D H 0.9986 0.2081 0.6718 0.105 Uiso 0.883(6) 1 calc PR A 1 H22D H 1.0176 0.1344 0.5803 0.105 Uiso 0.883(6) 1 calc PR A 1 H23D H 0.9008 0.2028 0.5478 0.105 Uiso 0.883(6) 1 calc PR A 1 N12D N 1.049(4) 0.4325(15) 0.576(2) 0.063(9) Uani 0.117(6) 1 d PD A 2 C12D C 1.045(2) 0.3319(16) 0.6090(18) 0.050 Uiso 0.117(6) 1 d PD A 2 C22D C 1.0500(18) 0.2114(17) 0.6676(18) 0.050 Uiso 0.117(6) 1 d PD A 2 H24D H 1.1219 0.2056 0.7343 0.075 Uiso 0.117(6) 1 calc PR A 2 H25D H 1.0408 0.1351 0.6207 0.075 Uiso 0.117(6) 1 calc PR A 2 H26D H 0.9904 0.2121 0.6874 0.075 Uiso 0.117(6) 1 calc PR A 2 O1W O 1.11173(13) 0.22301(18) -0.13347(17) 0.0405(5) Uani 0.861(7) 1 d PD . . H1W H 1.166(3) 0.181(4) -0.124(3) 0.061 Uiso 0.861(7) 1 d PD . . H2W H 1.084(3) 0.176(4) -0.101(3) 0.061 Uiso 0.861(7) 1 d PD . . 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 0.0268(4) 0.0249(5) 0.0139(4) 0.0038(3) 0.0065(3) -0.0081(4) O2A 0.0539(7) 0.0237(5) 0.0193(4) -0.0032(4) 0.0228(5) -0.0147(5) O3A 0.0288(4) 0.0145(4) 0.0156(4) 0.0007(3) 0.0101(3) 0.0008(3) N1A 0.0126(4) 0.0128(4) 0.0144(4) -0.0010(3) 0.0054(3) 0.0012(3) N2A 0.0227(5) 0.0155(4) 0.0126(4) 0.0001(3) 0.0071(3) -0.0073(3) C1A 0.0137(4) 0.0130(4) 0.0127(4) -0.0003(3) 0.0049(3) -0.0012(3) C2A 0.0225(5) 0.0222(5) 0.0175(5) -0.0019(4) 0.0117(4) -0.0001(4) C3A 0.0484(9) 0.0330(8) 0.0436(9) 0.0078(7) 0.0321(8) 0.0215(7) C4A 0.0203(5) 0.0361(7) 0.0236(6) -0.0005(5) 0.0121(5) -0.0068(5) C5A 0.0173(4) 0.0130(4) 0.0137(4) -0.0004(3) 0.0070(4) -0.0019(3) C6A 0.0229(5) 0.0152(5) 0.0143(4) -0.0025(4) 0.0104(4) -0.0072(4) C7A 0.0258(6) 0.0249(6) 0.0296(6) -0.0071(5) 0.0170(5) -0.0044(5) C8A 0.0173(4) 0.0159(5) 0.0127(4) -0.0018(4) 0.0078(4) -0.0044(4) O1B 0.0109(3) 0.0188(4) 0.0209(4) -0.0066(3) 0.0070(3) -0.0029(3) O2B 0.0117(3) 0.0189(4) 0.0262(4) -0.0064(3) 0.0059(3) -0.0014(3) O3B 0.0139(3) 0.0139(4) 0.0249(4) -0.0017(3) 0.0079(3) 0.0006(3) N1B 0.0114(3) 0.0128(4) 0.0145(4) 0.0001(3) 0.0068(3) 0.0008(3) N2B 0.0106(3) 0.0147(4) 0.0196(4) -0.0051(3) 0.0074(3) -0.0014(3) C1B 0.0096(4) 0.0118(4) 0.0138(4) -0.0011(3) 0.0059(3) 0.0003(3) C2B 0.0129(4) 0.0157(5) 0.0148(4) -0.0002(4) 0.0052(4) 0.0010(3) C3B 0.0263(6) 0.0198(5) 0.0223(5) 0.0046(4) 0.0115(5) -0.0008(5) C4B 0.0169(5) 0.0241(6) 0.0163(5) -0.0050(4) 0.0066(4) -0.0010(4) C5B 0.0114(4) 0.0120(4) 0.0145(4) -0.0013(3) 0.0069(3) -0.0008(3) C6B 0.0122(4) 0.0137(4) 0.0171(4) -0.0037(4) 0.0065(4) 0.0006(3) C7B 0.0244(6) 0.0271(6) 0.0180(5) -0.0003(5) 0.0084(5) 0.0067(5) C8B 0.0107(4) 0.0159(5) 0.0148(4) -0.0025(4) 0.0059(4) 0.0010(3) O1C 0.0219(4) 0.0189(4) 0.0196(4) -0.0015(3) 0.0132(3) -0.0074(3) O2C 0.0159(3) 0.0137(4) 0.0230(4) -0.0015(3) 0.0091(3) 0.0026(3) O3C 0.0204(4) 0.0120(4) 0.0242(4) -0.0012(3) 0.0085(3) -0.0045(3) N1C 0.0146(4) 0.0138(4) 0.0125(4) 0.0006(3) 0.0080(3) 0.0007(3) N2C 0.0157(4) 0.0099(4) 0.0140(4) -0.0015(3) 0.0087(3) -0.0022(3) C1C 0.0137(4) 0.0134(4) 0.0124(4) 0.0000(3) 0.0077(3) -0.0002(3) C2C 0.0141(4) 0.0214(5) 0.0204(5) 0.0012(4) 0.0092(4) 0.0020(4) C3C 0.0255(7) 0.0339(8) 0.0616(12) 0.0266(8) 0.0184(7) 0.0140(6) C4C 0.0172(5) 0.0378(8) 0.0241(6) -0.0064(6) 0.0049(5) -0.0001(5) C5C 0.0136(4) 0.0113(4) 0.0150(4) -0.0008(3) 0.0086(4) 0.0000(3) C6C 0.0136(4) 0.0098(4) 0.0145(4) -0.0013(3) 0.0075(3) -0.0002(3) C7C 0.0224(5) 0.0163(5) 0.0145(4) 0.0006(4) 0.0093(4) 0.0008(4) C8C 0.0162(4) 0.0106(4) 0.0142(4) -0.0006(3) 0.0090(4) 0.0001(3) N1D 0.121(4) 0.138(6) 0.067(3) 0.029(3) 0.029(3) -0.022(4) C1D 0.064(2) 0.093(3) 0.0349(14) 0.0059(16) 0.0181(14) 0.0089(19) C2D 0.087(3) 0.066(2) 0.0556(18) 0.0028(15) 0.0331(18) 0.0070(18) N12D 0.14(2) 0.018(7) 0.034(9) -0.001(6) 0.041(12) -0.024(9) O1W 0.0270(7) 0.0357(9) 0.0643(12) 0.0127(7) 0.0263(7) 0.0023(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 O1A C5A 1.2401(15) . ? O2A C8A 1.2468(15) . ? O3A C8A 1.2622(15) . ? N1A C1A 1.4940(15) . ? N1A H1A 0.91(2) . ? N1A H2A 0.86(2) . ? N1A H3A 0.90(2) . ? N2A C5A 1.3365(15) . ? N2A C6A 1.4618(15) . ? N2A H4A 0.83(2) . ? C1A C5A 1.5257(16) . ? C1A C2A 1.5454(17) . ? C1A H11A 1.0000 . ? C2A C4A 1.527(2) . ? C2A C3A 1.532(2) . ? C2A H21A 1.0000 . ? C3A H31A 0.9800 . ? C3A H32A 0.9800 . ? C3A H33A 0.9800 . ? C4A H41A 0.9800 . ? C4A H42A 0.9800 . ? C4A H43A 0.9800 . ? C6A C7A 1.529(2) . ? C6A C8A 1.5401(16) . ? C6A H61A 1.0000 . ? C7A H71A 0.9800 . ? C7A H72A 0.9800 . ? C7A H73A 0.9800 . ? O1B C5B 1.2419(13) . ? O2B C8B 1.2565(14) . ? O3B C8B 1.2598(14) . ? N1B C1B 1.4993(14) . ? N1B H1B 0.90(2) . ? N1B H2B 0.90(2) . ? N1B H3B 0.90(2) . ? N2B C5B 1.3357(14) . ? N2B C6B 1.4617(15) . ? N2B H4B 0.82(2) . ? C1B C5B 1.5268(15) . ? C1B C2B 1.5401(16) . ? C1B H11B 1.0000 . ? C2B C3B 1.5270(18) . ? C2B C4B 1.5310(17) . ? C2B H21B 1.0000 . ? C3B H31B 0.9800 . ? C3B H32B 0.9800 . ? C3B H33B 0.9800 . ? C4B H41B 0.9800 . ? C4B H42B 0.9800 . ? C4B H43B 0.9800 . ? C6B C8B 1.5376(15) . ? C6B C7B 1.5380(18) . ? C6B H61B 1.0000 . ? C7B H71B 0.9800 . ? C7B H72B 0.9800 . ? C7B H73B 0.9800 . ? O1C C5C 1.2391(14) . ? O2C C8C 1.2595(14) . ? O3C C8C 1.2646(14) . ? N1C C1C 1.4901(14) . ? N1C H1C 0.90(2) . ? N1C H2C 0.90(2) . ? N1C H3C 0.88(2) . ? N2C C5C 1.3395(14) . ? N2C C6C 1.4560(14) . ? N2C H4C 0.83(2) . ? C1C C5C 1.5280(15) . ? C1C C2C 1.5394(16) . ? C1C H11C 1.0000 . ? C2C C3C 1.523(2) . ? C2C C4C 1.529(2) . ? C2C H21C 1.0000 . ? C3C H31C 0.9800 . ? C3C H32C 0.9800 . ? C3C H33C 0.9800 . ? C4C H41C 0.9800 . ? C4C H42C 0.9800 . ? C4C H43C 0.9800 . ? C6C C7C 1.5356(16) . ? C6C C8C 1.5363(15) . ? C6C H61C 1.0000 . ? C7C H71C 0.9800 . ? C7C H72C 0.9800 . ? C7C H73C 0.9800 . ? N1D C1D 1.126(7) . ? C1D C2D 1.451(6) . ? C2D H21D 0.9800 . ? C2D H22D 0.9800 . ? C2D H23D 0.9800 . ? N12D C12D 1.128(7) . ? C12D C22D 1.453(7) . ? C22D H24D 0.9800 . ? C22D H25D 0.9800 . ? C22D H26D 0.9800 . ? O1W H1W 0.81(3) . ? O1W H2W 0.86(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A N1A H1A 102.9(13) . . ? C1A N1A H2A 114.2(14) . . ? H1A N1A H2A 111(2) . . ? C1A N1A H3A 109.3(14) . . ? H1A N1A H3A 116(2) . . ? H2A N1A H3A 104.5(19) . . ? C5A N2A C6A 122.34(10) . . ? C5A N2A H4A 117.8(15) . . ? C6A N2A H4A 119.8(15) . . ? N1A C1A C5A 107.08(9) . . ? N1A C1A C2A 112.45(9) . . ? C5A C1A C2A 111.58(10) . . ? N1A C1A H11A 108.5 . . ? C5A C1A H11A 108.5 . . ? C2A C1A H11A 108.5 . . ? C4A C2A C3A 111.06(13) . . ? C4A C2A C1A 111.27(11) . . ? C3A C2A C1A 113.11(11) . . ? C4A C2A H21A 107.0 . . ? C3A C2A H21A 107.0 . . ? C1A C2A H21A 107.0 . . ? C2A C3A H31A 109.5 . . ? C2A C3A H32A 109.5 . . ? H31A C3A H32A 109.5 . . ? C2A C3A H33A 109.5 . . ? H31A C3A H33A 109.5 . . ? H32A C3A H33A 109.5 . . ? C2A C4A H41A 109.5 . . ? C2A C4A H42A 109.5 . . ? H41A C4A H42A 109.5 . . ? C2A C4A H43A 109.5 . . ? H41A C4A H43A 109.5 . . ? H42A C4A H43A 109.5 . . ? O1A C5A N2A 124.85(11) . . ? O1A C5A C1A 120.31(10) . . ? N2A C5A C1A 114.82(10) . . ? N2A C6A C7A 110.96(11) . . ? N2A C6A C8A 109.87(9) . . ? C7A C6A C8A 109.08(10) . . ? N2A C6A H61A 109.0 . . ? C7A C6A H61A 109.0 . . ? C8A C6A H61A 109.0 . . ? C6A C7A H71A 109.5 . . ? C6A C7A H72A 109.5 . . ? H71A C7A H72A 109.5 . . ? C6A C7A H73A 109.5 . . ? H71A C7A H73A 109.5 . . ? H72A C7A H73A 109.5 . . ? O2A C8A O3A 125.43(11) . . ? O2A C8A C6A 117.12(11) . . ? O3A C8A C6A 117.36(10) . . ? C1B N1B H1B 106.2(13) . . ? C1B N1B H2B 111.7(12) . . ? H1B N1B H2B 105.5(19) . . ? C1B N1B H3B 111.4(13) . . ? H1B N1B H3B 106.8(18) . . ? H2B N1B H3B 114.5(19) . . ? C5B N2B C6B 120.30(9) . . ? C5B N2B H4B 121.8(15) . . ? C6B N2B H4B 117.9(15) . . ? N1B C1B C5B 106.50(8) . . ? N1B C1B C2B 112.84(9) . . ? C5B C1B C2B 112.19(9) . . ? N1B C1B H11B 108.4 . . ? C5B C1B H11B 108.4 . . ? C2B C1B H11B 108.4 . . ? C3B C2B C4B 112.49(11) . . ? C3B C2B C1B 112.52(10) . . ? C4B C2B C1B 111.51(10) . . ? C3B C2B H21B 106.6 . . ? C4B C2B H21B 106.6 . . ? C1B C2B H21B 106.6 . . ? C2B C3B H31B 109.5 . . ? C2B C3B H32B 109.5 . . ? H31B C3B H32B 109.5 . . ? C2B C3B H33B 109.5 . . ? H31B C3B H33B 109.5 . . ? H32B C3B H33B 109.5 . . ? C2B C4B H41B 109.5 . . ? C2B C4B H42B 109.5 . . ? H41B C4B H42B 109.5 . . ? C2B C4B H43B 109.5 . . ? H41B C4B H43B 109.5 . . ? H42B C4B H43B 109.5 . . ? O1B C5B N2B 123.35(10) . . ? O1B C5B C1B 119.96(9) . . ? N2B C5B C1B 116.66(9) . . ? N2B C6B C8B 109.96(9) . . ? N2B C6B C7B 111.80(10) . . ? C8B C6B C7B 109.15(10) . . ? N2B C6B H61B 108.6 . . ? C8B C6B H61B 108.6 . . ? C7B C6B H61B 108.6 . . ? C6B C7B H71B 109.5 . . ? C6B C7B H72B 109.5 . . ? H71B C7B H72B 109.5 . . ? C6B C7B H73B 109.5 . . ? H71B C7B H73B 109.5 . . ? H72B C7B H73B 109.5 . . ? O2B C8B O3B 126.04(11) . . ? O2B C8B C6B 116.93(10) . . ? O3B C8B C6B 116.96(10) . . ? C1C N1C H1C 103.6(13) . . ? C1C N1C H2C 119.1(13) . . ? H1C N1C H2C 110.9(19) . . ? C1C N1C H3C 111.5(14) . . ? H1C N1C H3C 107.6(19) . . ? H2C N1C H3C 103.8(19) . . ? C5C N2C C6C 119.36(9) . . ? C5C N2C H4C 114.1(13) . . ? C6C N2C H4C 123.3(13) . . ? N1C C1C C5C 106.60(9) . . ? N1C C1C C2C 112.45(9) . . ? C5C C1C C2C 112.25(9) . . ? N1C C1C H11C 108.5 . . ? C5C C1C H11C 108.5 . . ? C2C C1C H11C 108.5 . . ? C3C C2C C4C 111.89(13) . . ? C3C C2C C1C 113.66(11) . . ? C4C C2C C1C 110.93(11) . . ? C3C C2C H21C 106.6 . . ? C4C C2C H21C 106.6 . . ? C1C C2C H21C 106.6 . . ? C2C C3C H31C 109.5 . . ? C2C C3C H32C 109.5 . . ? H31C C3C H32C 109.5 . . ? C2C C3C H33C 109.5 . . ? H31C C3C H33C 109.5 . . ? H32C C3C H33C 109.5 . . ? C2C C4C H41C 109.5 . . ? C2C C4C H42C 109.5 . . ? H41C C4C H42C 109.5 . . ? C2C C4C H43C 109.5 . . ? H41C C4C H43C 109.5 . . ? H42C C4C H43C 109.5 . . ? O1C C5C N2C 124.18(10) . . ? O1C C5C C1C 120.20(10) . . ? N2C C5C C1C 115.60(9) . . ? N2C C6C C7C 110.08(9) . . ? N2C C6C C8C 111.33(9) . . ? C7C C6C C8C 107.64(9) . . ? N2C C6C H61C 109.3 . . ? C7C C6C H61C 109.3 . . ? C8C C6C H61C 109.3 . . ? C6C C7C H71C 109.5 . . ? C6C C7C H72C 109.5 . . ? H71C C7C H72C 109.5 . . ? C6C C7C H73C 109.5 . . ? H71C C7C H73C 109.5 . . ? H72C C7C H73C 109.5 . . ? O2C C8C O3C 125.91(11) . . ? O2C C8C C6C 117.63(10) . . ? O3C C8C C6C 116.22(10) . . ? N1D C1D C2D 177.9(5) . . ? C1D C2D H21D 109.5 . . ? C1D C2D H22D 109.5 . . ? H21D C2D H22D 109.5 . . ? C1D C2D H23D 109.5 . . ? H21D C2D H23D 109.5 . . ? H22D C2D H23D 109.5 . . ? N12D C12D C22D 171.5(18) . . ? C12D C22D H24D 109.5 . . ? C12D C22D H25D 109.5 . . ? H24D C22D H25D 109.5 . . ? C12D C22D H26D 109.5 . . ? H24D C22D H26D 109.5 . . ? H25D C22D H26D 109.5 . . ? H1W O1W H2W 103(4) . . ? 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 N1A C1A C2A C4A -72.89(13) . . . . ? C5A C1A C2A C4A 166.77(10) . . . . ? N1A C1A C2A C3A 52.94(16) . . . . ? C5A C1A C2A C3A -67.40(15) . . . . ? C6A N2A C5A O1A -2.9(2) . . . . ? C6A N2A C5A C1A 175.28(11) . . . . ? N1A C1A C5A O1A -18.18(15) . . . . ? C2A C1A C5A O1A 105.27(13) . . . . ? N1A C1A C5A N2A 163.52(10) . . . . ? C2A C1A C5A N2A -73.04(13) . . . . ? C5A N2A C6A C7A 113.16(14) . . . . ? C5A N2A C6A C8A -126.14(12) . . . . ? N2A C6A C8A O2A -44.97(16) . . . . ? C7A C6A C8A O2A 76.87(14) . . . . ? N2A C6A C8A O3A 138.35(12) . . . . ? C7A C6A C8A O3A -99.82(13) . . . . ? N1B C1B C2B C3B 56.50(13) . . . . ? C5B C1B C2B C3B -63.81(12) . . . . ? N1B C1B C2B C4B -70.98(12) . . . . ? C5B C1B C2B C4B 168.71(9) . . . . ? C6B N2B C5B O1B -4.98(18) . . . . ? C6B N2B C5B C1B 172.98(10) . . . . ? N1B C1B C5B O1B -10.91(14) . . . . ? C2B C1B C5B O1B 113.01(12) . . . . ? N1B C1B C5B N2B 171.06(10) . . . . ? C2B C1B C5B N2B -65.02(13) . . . . ? C5B N2B C6B C8B -150.21(11) . . . . ? C5B N2B C6B C7B 88.39(13) . . . . ? N2B C6B C8B O2B -34.48(14) . . . . ? C7B C6B C8B O2B 88.50(13) . . . . ? N2B C6B C8B O3B 148.47(11) . . . . ? C7B C6B C8B O3B -88.55(14) . . . . ? N1C C1C C2C C3C 59.47(16) . . . . ? C5C C1C C2C C3C -60.73(16) . . . . ? N1C C1C C2C C4C -67.63(13) . . . . ? C5C C1C C2C C4C 172.17(11) . . . . ? C6C N2C C5C O1C 3.02(17) . . . . ? C6C N2C C5C C1C -178.71(9) . . . . ? N1C C1C C5C O1C -35.78(13) . . . . ? C2C C1C C5C O1C 87.76(13) . . . . ? N1C C1C C5C N2C 145.88(10) . . . . ? C2C C1C C5C N2C -90.58(12) . . . . ? C5C N2C C6C C7C 174.08(10) . . . . ? C5C N2C C6C C8C -66.64(13) . . . . ? N2C C6C C8C O2C -35.21(14) . . . . ? C7C C6C C8C O2C 85.51(12) . . . . ? N2C C6C C8C O3C 149.98(10) . . . . ? C7C C6C C8C O3C -89.30(12) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.389 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.051 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_publ_flag _geom_hbond_site_symmetry_A N1A H1A O1C 0.91(2) 1.93(2) 2.7902(13) 157(2) y 2_656 N1A H2A O3B 0.86(2) 1.90(2) 2.7515(14) 166(2) y 1_566 N1A H3A O2B 0.90(2) 1.99(2) 2.7888(13) 147.5(19) y 2_756 N2A H4A O3A 0.83(2) 2.12(2) 2.9409(14) 169(2) y 2_656 C1A H11A O2A 1.00 2.30 3.2883(16) 169.7 y 2_656 N1B H1B O1A 0.90(2) 1.94(2) 2.7324(14) 144.6(18) y 1_554 N1B H2B O3C 0.90(2) 1.85(2) 2.7379(14) 167.9(19) y 2_655 N1B H3B O2C 0.90(2) 2.17(2) 3.0525(14) 166.4(18) y 1_555 N2B H4B O3B 0.82(2) 2.24(2) 3.0203(13) 160(2) y 2_755 C1B H11B O2B 1.00 2.32 3.3059(14) 166.6 y 2_755 N1C H1C O1B 0.90(2) 1.94(2) 2.7175(13) 143.5(18) y 2_655 N1C H2C O3A 0.90(2) 1.81(2) 2.6957(14) 166.1(19) y 2_656 N1C H3C O2A 0.88(2) 1.93(2) 2.7368(14) 151.1(19) y 1_555 N2C H4C O2C 0.83(2) 1.95(2) 2.7686(13) 169.7(18) y 2_655 C6C H61C O1W 1.00 2.50 3.3454(18) 141.5 y 1_455 C2D H21D O1W 0.98 2.39 3.319(4) 157.1 y 1_556 C2D H22D N1D 0.98 2.66 3.429(8) 135.1 y 2_746 O1W H1W O3C 0.81(3) 2.08(3) 2.8731(18) 168(4) y 1_655 O1W H2W O2B 0.86(3) 2.03(3) 2.871(2) 168(4) y 1_555 data_VA _database_code_depnum_ccdc_archive 'CCDC 283666' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Valyl-L-alanine ; _chemical_name_common L-Valyl-L-alanine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8.41 H16 N2 O3' _chemical_formula_weight 193.15 _chemical_absolute_configuration 'known for the purchased material' 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 Hexagonal _symmetry_space_group_name_H-M 'P 61' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 14.4539(18) _cell_length_b 14.4539(18) _cell_length_c 9.996(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1808.6(6) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 1887 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.02 _exptl_crystal_description 'Thick needle' _exptl_crystal_colour Colourless _exptl_crystal_size_max 1.200 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.064 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 627 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8156 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 105(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_% none _diffrn_reflns_number 4998 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 26.02 _reflns_number_total 1247 _reflns_number_gt 1035 _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 ; 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^)+(0.0405P)^2^+0.4285P] 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 1247 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.019 _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 O1 O 0.62467(15) 0.31009(16) 0.7324(2) 0.0302(5) Uani 1 1 d . . . O2 O 0.50940(18) 0.56317(18) 0.8320(2) 0.0373(6) Uani 1 1 d . . . O3 O 0.59378(16) 0.56626(16) 1.0212(2) 0.0278(5) Uani 1 1 d . . . N1 N 0.5298(2) 0.1979(2) 0.5216(3) 0.0222(5) Uani 1 1 d . . . H1 H 0.548(2) 0.164(2) 0.589(4) 0.033 Uiso 1 1 d . . . H2 H 0.600(3) 0.249(2) 0.481(4) 0.033 Uiso 1 1 d . . . H3 H 0.485(3) 0.147(3) 0.463(4) 0.033 Uiso 1 1 d . . . N2 N 0.55832(19) 0.42212(19) 0.7170(2) 0.0254(5) Uani 1 1 d . . . H4 H 0.519(2) 0.440(2) 0.677(4) 0.031 Uiso 1 1 d . . . C1 C 0.4854(2) 0.2651(2) 0.5713(3) 0.0216(6) Uani 1 1 d . . . H11 H 0.489(2) 0.311(2) 0.505(3) 0.026 Uiso 1 1 d . . . C2 C 0.3711(2) 0.1983(2) 0.6219(3) 0.0297(7) Uani 1 1 d . . . H21 H 0.3523 0.2483 0.6673 0.036 Uiso 1 1 calc R . . C3 C 0.3578(3) 0.1143(3) 0.7256(4) 0.0486(9) Uani 1 1 d . . . H31 H 0.3695 0.0600 0.6825 0.073 Uiso 1 1 calc R . . H32 H 0.2855 0.0803 0.7628 0.073 Uiso 1 1 calc R . . H33 H 0.4101 0.1488 0.7976 0.073 Uiso 1 1 calc R . . C4 C 0.2926(2) 0.1465(3) 0.5058(4) 0.0389(8) Uani 1 1 d . . . H41 H 0.2195 0.1075 0.5408 0.058 Uiso 1 1 calc R . . H42 H 0.3088 0.0968 0.4587 0.058 Uiso 1 1 calc R . . H43 H 0.2993 0.2020 0.4438 0.058 Uiso 1 1 calc R . . C5 C 0.5631(2) 0.3364(2) 0.6807(3) 0.0233(6) Uani 1 1 d . . . C6 C 0.6240(2) 0.4892(2) 0.8279(3) 0.0257(7) Uani 1 1 d . . . H61 H 0.6327 0.4422 0.8941 0.031 Uiso 1 1 calc R . . C7 C 0.7347(2) 0.5736(3) 0.7807(4) 0.0426(9) Uani 1 1 d . . . H71 H 0.7687 0.5389 0.7339 0.064 Uiso 1 1 calc R . . H72 H 0.7782 0.6130 0.8580 0.064 Uiso 1 1 calc R . . H73 H 0.7282 0.6232 0.7197 0.064 Uiso 1 1 calc R . . C8 C 0.5688(2) 0.5423(2) 0.8985(3) 0.0233(6) Uani 1 1 d . . . C1S C 0.106(9) 0.106(10) 0.181(17) 0.19(3) Uiso 0.137(9) 1 d P . . C2S C 0.074(12) 0.134(8) 0.264(17) 0.19(3) Uiso 0.137(9) 1 d P . . C3S C 0.025(7) 0.030(6) 0.087(14) 0.19(3) Uiso 0.137(9) 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0376(11) 0.0375(12) 0.0242(11) -0.0068(9) -0.0106(10) 0.0254(10) O2 0.0470(13) 0.0553(14) 0.0259(12) -0.0140(11) -0.0156(11) 0.0376(12) O3 0.0395(11) 0.0388(11) 0.0138(11) -0.0040(9) -0.0030(9) 0.0260(10) N1 0.0264(13) 0.0245(12) 0.0152(12) 0.0006(10) -0.0005(10) 0.0125(11) N2 0.0350(14) 0.0307(13) 0.0154(12) -0.0044(10) -0.0070(11) 0.0199(11) C1 0.0283(15) 0.0253(15) 0.0136(14) 0.0008(11) -0.0008(12) 0.0152(12) C2 0.0293(16) 0.0351(16) 0.0263(17) -0.0065(13) 0.0002(13) 0.0172(13) C3 0.0388(19) 0.058(2) 0.033(2) 0.0134(18) 0.0086(16) 0.0127(17) C4 0.0299(16) 0.0453(19) 0.0381(19) -0.0086(15) -0.0052(15) 0.0164(15) C5 0.0264(14) 0.0269(14) 0.0168(14) 0.0011(12) 0.0017(12) 0.0135(12) C6 0.0297(15) 0.0329(16) 0.0176(15) -0.0067(12) -0.0063(12) 0.0180(13) C7 0.0338(18) 0.052(2) 0.034(2) -0.0183(17) -0.0002(15) 0.0155(16) C8 0.0254(15) 0.0260(14) 0.0199(16) -0.0019(13) -0.0022(12) 0.0139(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.242(3) . ? O2 C8 1.237(3) . ? O3 C8 1.276(3) . ? N1 C1 1.491(3) . ? N1 H1 0.94(4) . ? N1 H2 0.99(3) . ? N1 H3 0.91(4) . ? N2 C5 1.325(4) . ? N2 C6 1.466(4) . ? N2 H4 0.84(3) . ? C1 C2 1.524(4) . ? C1 C5 1.537(4) . ? C1 H11 0.93(3) . ? C2 C4 1.532(4) . ? C2 C3 1.535(5) . ? C2 H21 1.0000 . ? C3 H31 0.9800 . ? C3 H32 0.9800 . ? C3 H33 0.9800 . ? C4 H41 0.9800 . ? C4 H42 0.9800 . ? C4 H43 0.9800 . ? C6 C7 1.522(4) . ? C6 C8 1.528(4) . ? C6 H61 1.0000 . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C1S C2S 1.12(11) . ? C1S C2S 1.25(10) 5_554 ? C1S C3S 1.48(15) . ? C1S C3S 1.61(16) 6 ? C2S C1S 1.25(10) 6 ? C2S C3S 1.41(12) 6 ? C3S C2S 1.41(12) 5_554 ? C3S C1S 1.61(16) 5_554 ? 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 C1 N1 H1 115(2) . . ? C1 N1 H2 105.1(17) . . ? H1 N1 H2 104(3) . . ? C1 N1 H3 112(2) . . ? H1 N1 H3 108(3) . . ? H2 N1 H3 113(3) . . ? C5 N2 C6 120.4(2) . . ? C5 N2 H4 121(2) . . ? C6 N2 H4 119(2) . . ? N1 C1 C2 112.4(2) . . ? N1 C1 C5 105.5(2) . . ? C2 C1 C5 112.7(2) . . ? N1 C1 H11 110.0(19) . . ? C2 C1 H11 110.3(18) . . ? C5 C1 H11 105.7(19) . . ? C1 C2 C4 111.2(3) . . ? C1 C2 C3 113.1(2) . . ? C4 C2 C3 110.8(3) . . ? C1 C2 H21 107.1 . . ? C4 C2 H21 107.1 . . ? C3 C2 H21 107.1 . . ? C2 C3 H31 109.5 . . ? C2 C3 H32 109.5 . . ? H31 C3 H32 109.5 . . ? C2 C3 H33 109.5 . . ? H31 C3 H33 109.5 . . ? H32 C3 H33 109.5 . . ? C2 C4 H41 109.5 . . ? C2 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C2 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? O1 C5 N2 123.6(3) . . ? O1 C5 C1 119.0(2) . . ? N2 C5 C1 117.4(2) . . ? N2 C6 C7 111.6(2) . . ? N2 C6 C8 110.7(2) . . ? C7 C6 C8 110.1(2) . . ? N2 C6 H61 108.1 . . ? C7 C6 H61 108.1 . . ? C8 C6 H61 108.1 . . ? C6 C7 H71 109.5 . . ? C6 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? C6 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? O2 C8 O3 125.9(3) . . ? O2 C8 C6 118.3(3) . . ? O3 C8 C6 115.6(2) . . ? 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 N1 C1 C2 C4 -72.8(3) . . . . ? C5 C1 C2 C4 168.2(2) . . . . ? N1 C1 C2 C3 52.7(3) . . . . ? C5 C1 C2 C3 -66.4(3) . . . . ? C6 N2 C5 O1 -3.1(4) . . . . ? C6 N2 C5 C1 175.2(2) . . . . ? N1 C1 C5 O1 -18.8(3) . . . . ? C2 C1 C5 O1 104.2(3) . . . . ? N1 C1 C5 N2 162.8(2) . . . . ? C2 C1 C5 N2 -74.2(3) . . . . ? C5 N2 C6 C7 86.6(3) . . . . ? C5 N2 C6 C8 -150.4(2) . . . . ? N2 C6 C8 O2 -30.2(4) . . . . ? C7 C6 C8 O2 93.7(3) . . . . ? N2 C6 C8 O3 153.5(2) . . . . ? C7 C6 C8 O3 -82.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.167 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.039 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_publ_flag _geom_hbond_site_symmetry_A N1 H1 O2 0.94(4) 1.88(4) 2.764(3) 156(3) y 5_554 N1 H2 O1 0.99(3) 1.81(3) 2.715(3) 150(3) y 3_664 N1 H3 O3 0.91(4) 1.86(4) 2.713(3) 157(3) y 2_654 N2 H4 O3 0.84(3) 2.22(4) 3.011(3) 158(3) y 4_664 C1 H11 O2 0.93(3) 2.50(3) 3.422(4) 177(2) y 4_664 # start Validation Reply Form #_vrf_PLAT063_VA #; #PROBLEM: Crystal Probably too Large for Beam Size ....... 1.35 mm #RESPONSE: This is no problem for a light atom structure, see Gorbitz, Acta #Cryst. B55 (1999) 1090-98. #; # end Validation Reply Form # start Validation Reply Form #_vrf_PLAT063_VA-aw #; #PROBLEM: Crystal Probably too Large for Beam Size ....... 1.20 mm #RESPONSE: This is no problem for a light atom structure, see Gorbitz, Acta #Cryst. B55 (1999) 1090-98. #; #_vrf_PLAT432_VA-aw #; #PROBLEM: Short Inter X...Y Contact O1W .. C22D .. 2.48 Ang. #RESPONSE: C22D has low occupancy and is only present when O1W is not. #Accordingly, this is not a true contact #; # end Validation Reply Form data_VS-tfe _database_code_depnum_ccdc_archive 'CCDC 283667' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Valyl-L-serine trifluoroethanol solvate ; _chemical_name_common 'L-Valyl-L-serine trifluoroethanol solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8.28 H16 F0.85 N2 O4.13' _chemical_formula_weight 225.91 _chemical_absolute_configuration 'known for the purchased material' 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' F F 0.0171 0.0103 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.0668(13) _cell_length_b 9.8053(10) _cell_length_c 14.1915(14) _cell_angle_alpha 90.00 _cell_angle_beta 116.172(2) _cell_angle_gamma 90.00 _cell_volume 1756.7(3) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4235 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 26.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 723 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8315 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 105(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_% ? _diffrn_reflns_number 10658 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3807 _reflns_number_gt 3233 _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 three sets of exposures with the detector set at 2\q = 29\%, 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^)+(0.0614P)^2^+0.5685P] 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 3807 _refine_ls_number_parameters 538 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0.007 _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 0.80348(19) 0.5348(4) 0.70304(19) 0.0286(6) Uani 1 1 d . . . O3A O 0.45543(19) 0.5629(4) 0.4055(2) 0.0266(6) Uani 1 1 d . A . O4A O 0.52446(19) 0.7728(4) 0.4484(2) 0.0263(6) Uani 1 1 d . A . N1A N 0.8271(2) 0.3233(5) 0.8199(2) 0.0222(6) Uani 1 1 d D A . H1A H 0.844(3) 0.253(4) 0.868(3) 0.033 Uiso 1 1 d D . . H2A H 0.859(3) 0.393(4) 0.866(3) 0.033 Uiso 1 1 d D . . H3A H 0.867(3) 0.309(5) 0.780(3) 0.033 Uiso 1 1 d D . . N2A N 0.6443(2) 0.4721(4) 0.5731(2) 0.0204(6) Uani 1 1 d D . . H4A H 0.589(2) 0.426(4) 0.558(3) 0.024 Uiso 1 1 d D . . C1A C 0.7164(3) 0.3460(5) 0.7375(3) 0.0190(7) Uani 1 1 d . . . H11A H 0.6908 0.2612 0.6945 0.023 Uiso 1 1 calc R A . C2A C 0.6414(3) 0.3799(5) 0.7870(3) 0.0228(8) Uani 1 1 d . A . H21A H 0.5700 0.3968 0.7275 0.027 Uiso 1 1 calc R . . C3A C 0.6711(3) 0.5092(6) 0.8539(4) 0.0398(11) Uani 1 1 d . . . H31A H 0.6784 0.5852 0.8127 0.060 Uiso 1 1 calc R A . H32A H 0.7384 0.4949 0.9162 0.060 Uiso 1 1 calc R . . H33A H 0.6156 0.5304 0.8755 0.060 Uiso 1 1 calc R . . C4A C 0.6292(3) 0.2562(6) 0.8470(3) 0.0374(10) Uani 1 1 d . . . H41A H 0.5738 0.2746 0.8694 0.056 Uiso 1 1 calc R A . H42A H 0.6965 0.2390 0.9088 0.056 Uiso 1 1 calc R . . H43A H 0.6097 0.1760 0.8011 0.056 Uiso 1 1 calc R . . C5A C 0.7245(3) 0.4597(5) 0.6682(3) 0.0185(7) Uani 1 1 d . A . C6A C 0.6426(3) 0.5818(5) 0.5023(3) 0.0207(7) Uani 0.810(9) 1 d P A 1 H61A H 0.6929 0.6547 0.5449 0.025 Uiso 1 1 calc R A 1 C7A C 0.6773(3) 0.5304(6) 0.4193(3) 0.0274(8) Uani 0.810(9) 1 d PD A 1 H71A H 0.6329 0.4512 0.3820 0.033 Uiso 0.810(9) 1 calc PR A 1 H72A H 0.6650 0.6034 0.3670 0.033 Uiso 0.810(9) 1 calc PR A 1 O2A O 0.7843(3) 0.4918(5) 0.4632(3) 0.0323(11) Uani 0.810(9) 1 d PD A 1 H5A H 0.812(3) 0.564(4) 0.452(4) 0.039 Uiso 0.810(9) 1 d PD A 1 C61A C 0.6426(3) 0.5818(5) 0.5023(3) 0.0207(7) Uani 0.190(9) 1 d P A 2 C71A C 0.6773(3) 0.5304(6) 0.4193(3) 0.0274(8) Uani 0.190(9) 1 d P A 2 H73A H 0.7374 0.4667 0.4540 0.033 Uiso 0.190(9) 1 calc PR A 2 H74A H 0.6180 0.4778 0.3656 0.033 Uiso 0.190(9) 1 calc PR A 2 O21A O 0.7047(13) 0.6218(19) 0.3730(13) 0.043(5) Uiso 0.190(9) 1 d P A 2 H51A H 0.6683 0.6130 0.3071 0.051 Uiso 0.190(9) 1 d PR A 2 C8A C 0.5309(3) 0.6435(5) 0.4478(3) 0.0204(7) Uani 1 1 d . . . O1B O -0.11382(19) 0.8343(4) 0.69111(17) 0.0250(6) Uani 1 1 d . . . O2B O -0.1468(2) 0.7735(5) 0.9910(2) 0.0313(6) Uani 1 1 d D . . H5B H -0.122(4) 0.705(4) 0.974(3) 0.047 Uiso 1 1 d D . . O3B O 0.0578(2) 1.0220(4) 1.0200(2) 0.0297(6) Uani 1 1 d . . . O4B O -0.09538(19) 1.1315(4) 0.97463(18) 0.0231(5) Uani 1 1 d . . . N1B N -0.0233(2) 0.6087(5) 0.6693(2) 0.0205(6) Uani 1 1 d D B . H1B H 0.018(3) 0.552(4) 0.652(3) 0.031 Uiso 1 1 d D . . H2B H -0.040(3) 0.679(4) 0.617(3) 0.031 Uiso 1 1 d D . . H3B H -0.086(3) 0.575(5) 0.667(3) 0.031 Uiso 1 1 d D . . N2B N -0.0353(2) 0.8259(5) 0.8687(2) 0.0235(6) Uani 1 1 d D . . H4B H 0.007(3) 0.783(4) 0.920(3) 0.028 Uiso 1 1 d D . . C1B C 0.0268(3) 0.6731(5) 0.7754(3) 0.0205(7) Uani 1 1 d . . . H11B H 0.0317 0.6032 0.8287 0.025 Uiso 1 1 calc R B . C2B C 0.1388(3) 0.7276(6) 0.8041(3) 0.0298(9) Uani 1 1 d . B . H21B H 0.1597 0.7851 0.8684 0.036 Uiso 1 1 calc R . . C3B C 0.1414(3) 0.8205(6) 0.7178(4) 0.0430(11) Uani 1 1 d . . . H31B H 0.0864 0.8905 0.6993 0.064 Uiso 1 1 calc R B . H32B H 0.1286 0.7658 0.6555 0.064 Uiso 1 1 calc R . . H33B H 0.2110 0.8644 0.7435 0.064 Uiso 1 1 calc R . . C4B C 0.2180(3) 0.6097(6) 0.8333(3) 0.0381(10) Uani 1 1 d . . . H41B H 0.2151 0.5569 0.8906 0.057 Uiso 1 1 calc R B . H42B H 0.2896 0.6462 0.8560 0.057 Uiso 1 1 calc R . . H43B H 0.1999 0.5507 0.7721 0.057 Uiso 1 1 calc R . . C5B C -0.0491(3) 0.7860(5) 0.7743(3) 0.0191(7) Uani 1 1 d . B . C6B C -0.1028(3) 0.9290(5) 0.8819(3) 0.0210(7) Uani 1 1 d . B 1 H61B H -0.1381 0.9794 0.8138 0.025 Uiso 1 1 calc R B 1 C7B C -0.1901(3) 0.8595(5) 0.9008(3) 0.0275(8) Uani 1 1 d D B 1 H71B H -0.2354 0.9298 0.9106 0.033 Uiso 1 1 calc R B 1 H72B H -0.2350 0.8045 0.8384 0.033 Uiso 1 1 calc R B 1 C8B C -0.0401(3) 1.0344(5) 0.9666(3) 0.0204(7) Uani 1 1 d . B 1 O1C O 0.1939(2) 0.6568(4) 0.3615(2) 0.0265(6) Uani 1 1 d . C 1 O2C O -0.0304(2) 0.8285(5) 0.2006(2) 0.0324(9) Uani 0.944(7) 1 d PD C 1 H5C H -0.074(3) 0.807(5) 0.134(2) 0.049 Uiso 1 1 d D D 1 O21C O -0.115(5) 0.810(7) 0.184(5) 0.050 Uiso 0.056(7) 1 d P C 2 O3C O -0.08536(19) 0.7204(4) 0.46926(19) 0.0249(6) Uani 1 1 d . . . O4C O -0.0748(2) 0.9277(4) 0.4081(2) 0.0244(6) Uani 1 1 d . . . N1C N 0.3055(2) 0.4363(5) 0.4493(2) 0.0196(6) Uani 1 1 d D . . H1C H 0.263(3) 0.407(5) 0.383(2) 0.029 Uiso 1 1 d D . . H2C H 0.358(3) 0.376(4) 0.487(3) 0.029 Uiso 1 1 d D . . H3C H 0.340(3) 0.492(4) 0.423(3) 0.029 Uiso 1 1 d D . . N2C N 0.0805(2) 0.6316(5) 0.4339(2) 0.0212(6) Uani 1 1 d D C . H4C H 0.065(3) 0.588(4) 0.474(3) 0.025 Uiso 1 1 d D . . C1C C 0.2392(3) 0.4898(5) 0.4988(3) 0.0196(7) Uani 1 1 d . C . H11C H 0.1935 0.4143 0.5032 0.024 Uiso 1 1 calc R . . C2C C 0.3061(3) 0.5464(5) 0.6100(3) 0.0260(8) Uani 1 1 d . . . H21C H 0.2575 0.6015 0.6295 0.031 Uiso 1 1 calc R . . C3C C 0.3941(3) 0.6415(6) 0.6156(3) 0.0371(10) Uani 1 1 d . . . H31C H 0.4272 0.6848 0.6848 0.056 Uiso 1 1 calc R . . H32C H 0.3643 0.7117 0.5612 0.056 Uiso 1 1 calc R . . H33C H 0.4474 0.5889 0.6042 0.056 Uiso 1 1 calc R . . C4C C 0.3487(3) 0.4301(6) 0.6892(3) 0.0306(9) Uani 1 1 d . . . H41C H 0.3902 0.4677 0.7596 0.046 Uiso 1 1 calc R . . H42C H 0.3938 0.3709 0.6704 0.046 Uiso 1 1 calc R . . H43C H 0.2893 0.3770 0.6884 0.046 Uiso 1 1 calc R . . C5C C 0.1682(3) 0.5995(5) 0.4240(3) 0.0209(7) Uani 1 1 d . . . C6C C 0.0192(3) 0.7483(5) 0.3757(3) 0.0205(7) Uani 1 1 d . . . H61C H 0.0708 0.8221 0.3820 0.025 Uiso 1 1 calc R C . C7C C -0.0453(3) 0.7182(5) 0.2579(3) 0.0259(8) Uani 1 1 d D C . H71C H -0.0209 0.6319 0.2395 0.031 Uiso 1 1 calc R E 1 H72C H -0.1213 0.7088 0.2406 0.031 Uiso 1 1 calc R E 1 C8C C -0.0521(3) 0.8035(5) 0.4224(3) 0.0195(7) Uani 1 1 d . C . O1W O 0.588(5) 0.847(7) 0.708(4) 0.05(2) Uiso 0.059(13) 1 d P . . O1D O 0.619(5) 0.675(6) 1.094(5) 0.21(2) Uiso 0.201(11) 1 d PD F 1 C1D C 0.647(3) 0.771(5) 1.034(4) 0.21(2) Uiso 0.201(11) 1 d PD F 1 C2D C 0.553(2) 0.861(3) 0.964(2) 0.21(2) Uiso 0.201(11) 1 d PD F 1 F1D F 0.520(3) 0.929(4) 1.024(3) 0.170(10) Uiso 0.201(11) 1 d PD F 1 F2D F 0.585(3) 0.947(4) 0.912(3) 0.170(10) Uiso 0.201(11) 1 d PD F 1 F3D F 0.477(3) 0.783(4) 0.897(3) 0.170(10) Uiso 0.201(11) 1 d PD F 1 O1E O 0.624(5) 0.736(12) 1.150(3) 0.21(2) Uiso 0.128(9) 1 d PD G 2 C1E C 0.633(3) 0.780(10) 1.058(4) 0.21(2) Uiso 0.128(9) 1 d PD G 2 C2E C 0.527(3) 0.782(5) 0.960(3) 0.21(2) Uiso 0.128(9) 1 d PD G 2 F1E F 0.542(4) 0.827(6) 0.880(3) 0.170(10) Uiso 0.128(9) 1 d PD G 2 F2E F 0.488(5) 0.658(5) 0.941(4) 0.170(10) Uiso 0.128(9) 1 d PD G 2 F3E F 0.461(5) 0.864(6) 0.977(5) 0.170(10) Uiso 0.128(9) 1 d PD G 2 C2F C 0.431(5) 1.012(8) 0.926(5) 0.150 Uiso 0.052(7) 1 d PD H 3 F1F F 0.465(9) 1.135(9) 0.965(9) 0.150 Uiso 0.052(7) 1 d PD H 3 F2F F 0.498(9) 0.920(12) 0.988(10) 0.150 Uiso 0.052(7) 1 d PD H 3 F3F F 0.336(6) 0.990(12) 0.921(8) 0.150 Uiso 0.052(7) 1 d PD H 3 F4F F 0.427(10) 1.003(15) 0.831(7) 0.150 Uiso 0.052(7) 1 d PD H 3 C2G C 0.447(2) 0.989(4) 0.911(2) 0.150 Uiso 0.129(8) 1 d PD I 4 F1G F 0.396(4) 0.891(4) 0.934(4) 0.150 Uiso 0.129(8) 1 d PD I 4 F2G F 0.489(4) 0.939(6) 0.851(4) 0.150 Uiso 0.129(8) 1 d PD I 4 F3G F 0.382(3) 1.089(5) 0.861(4) 0.150 Uiso 0.129(8) 1 d PD I 4 F4G F 0.524(3) 1.036(5) 0.999(3) 0.150 Uiso 0.129(8) 1 d PD I 4 F1H F 0.641(2) 0.764(4) 1.057(2) 0.150 Uiso 0.249(16) 1 d P J 5 F2H F 0.561(3) 0.829(5) 0.983(3) 0.150 Uiso 0.202(15) 1 d P J 5 F3I F 0.440(4) 0.898(7) 0.839(4) 0.150 Uiso 0.143(16) 1 d P J 5 F4H F 0.498(4) 0.924(6) 0.935(5) 0.150 Uiso 0.167(18) 1 d P J 5 F5H F 0.546(6) 0.928(9) 0.797(6) 0.150 Uiso 0.093(11) 1 d P K 5 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 0.0216(13) 0.0357(16) 0.0252(12) 0.0049(12) 0.0071(10) -0.0076(12) O3A 0.0203(13) 0.0232(14) 0.0351(14) 0.0007(11) 0.0110(11) -0.0048(11) O4A 0.0200(13) 0.0169(12) 0.0387(15) 0.0020(11) 0.0098(11) 0.0015(11) N1A 0.0215(15) 0.0254(17) 0.0181(14) 0.0029(13) 0.0074(12) 0.0012(13) N2A 0.0182(14) 0.0151(15) 0.0265(15) 0.0018(12) 0.0087(12) -0.0026(12) C1A 0.0180(17) 0.0181(17) 0.0205(16) -0.0005(13) 0.0081(13) -0.0010(14) C2A 0.0212(18) 0.0248(19) 0.0242(18) -0.0020(15) 0.0117(15) -0.0024(15) C3A 0.035(2) 0.041(3) 0.052(3) -0.019(2) 0.027(2) -0.006(2) C4A 0.037(2) 0.040(3) 0.045(2) 0.007(2) 0.027(2) -0.002(2) C5A 0.0171(17) 0.0201(18) 0.0200(16) -0.0009(13) 0.0098(14) 0.0007(14) C6A 0.0181(17) 0.0179(17) 0.0257(17) 0.0026(14) 0.0094(14) 0.0014(14) C7A 0.0252(19) 0.031(2) 0.0317(19) 0.0030(17) 0.0183(16) 0.0009(17) O2A 0.030(2) 0.031(2) 0.043(2) 0.0058(16) 0.0228(16) 0.0046(15) C61A 0.0181(17) 0.0179(17) 0.0257(17) 0.0026(14) 0.0094(14) 0.0014(14) C71A 0.0252(19) 0.031(2) 0.0317(19) 0.0030(17) 0.0183(16) 0.0009(17) C8A 0.0201(17) 0.0208(19) 0.0208(16) 0.0038(14) 0.0094(14) -0.0008(15) O1B 0.0257(13) 0.0282(14) 0.0190(12) 0.0004(11) 0.0078(10) 0.0043(11) O2B 0.0376(16) 0.0293(15) 0.0319(14) 0.0013(12) 0.0197(12) 0.0003(13) O3B 0.0245(14) 0.0216(14) 0.0330(14) -0.0017(11) 0.0036(12) 0.0021(11) O4B 0.0259(13) 0.0185(13) 0.0235(12) -0.0017(10) 0.0097(10) 0.0027(11) N1B 0.0235(16) 0.0206(16) 0.0211(14) -0.0006(12) 0.0134(13) -0.0004(13) N2B 0.0293(16) 0.0180(15) 0.0215(14) 0.0016(13) 0.0095(12) 0.0072(13) C1B 0.0224(17) 0.0205(18) 0.0172(16) 0.0004(13) 0.0073(14) 0.0019(14) C2B 0.0233(19) 0.034(2) 0.0294(19) -0.0100(17) 0.0094(15) -0.0006(17) C3B 0.032(2) 0.040(3) 0.066(3) -0.001(2) 0.029(2) -0.008(2) C4B 0.025(2) 0.050(3) 0.036(2) -0.004(2) 0.0105(17) 0.0071(19) C5B 0.0201(17) 0.0154(16) 0.0231(17) -0.0002(13) 0.0106(14) -0.0027(14) C6B 0.0229(18) 0.0189(17) 0.0192(16) 0.0008(14) 0.0076(14) 0.0050(15) C7B 0.0240(19) 0.026(2) 0.0305(19) -0.0030(16) 0.0099(15) 0.0008(16) C8B 0.0266(19) 0.0161(17) 0.0176(16) 0.0019(13) 0.0089(14) -0.0001(15) O1C 0.0281(13) 0.0240(14) 0.0353(14) 0.0082(11) 0.0211(11) 0.0038(11) O2C 0.044(2) 0.0274(16) 0.0212(14) 0.0044(12) 0.0107(13) -0.0064(14) O3C 0.0268(13) 0.0237(13) 0.0300(13) 0.0048(11) 0.0178(11) 0.0025(11) O4C 0.0285(13) 0.0194(13) 0.0325(13) 0.0017(10) 0.0199(11) 0.0047(11) N1C 0.0183(15) 0.0205(15) 0.0212(15) 0.0018(12) 0.0099(12) 0.0001(12) N2C 0.0228(15) 0.0197(16) 0.0253(15) 0.0055(12) 0.0144(12) 0.0025(13) C1C 0.0195(16) 0.0168(17) 0.0250(17) 0.0009(13) 0.0121(14) 0.0011(14) C2C 0.0280(19) 0.029(2) 0.0239(18) 0.0000(16) 0.0135(15) 0.0073(16) C3C 0.040(2) 0.034(2) 0.029(2) -0.0052(18) 0.0071(17) -0.008(2) C4C 0.0253(19) 0.038(2) 0.0292(19) 0.0064(17) 0.0128(16) 0.0071(18) C5C 0.0196(17) 0.0204(18) 0.0241(17) 0.0005(14) 0.0108(14) -0.0007(14) C6C 0.0248(18) 0.0173(18) 0.0222(17) 0.0049(13) 0.0128(14) 0.0050(14) C7C 0.029(2) 0.0220(19) 0.0304(19) 0.0008(16) 0.0169(16) 0.0011(16) C8C 0.0187(16) 0.0209(19) 0.0186(16) 0.0010(13) 0.0080(13) 0.0021(14) _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 C5A 1.239(4) . ? O3A C8A 1.245(4) . ? O4A C8A 1.272(5) . ? N1A C1A 1.495(4) . ? N1A H1A 0.92(3) . ? N1A H2A 0.92(3) . ? N1A H3A 0.97(3) . ? N2A C5A 1.329(4) . ? N2A C6A 1.465(4) . ? N2A H4A 0.85(3) . ? C1A C5A 1.523(5) . ? C1A C2A 1.541(5) . ? C1A H11A 1.0000 . ? C2A C3A 1.527(6) . ? C2A C4A 1.533(6) . ? C2A H21A 1.0000 . ? C3A H31A 0.9800 . ? C3A H32A 0.9800 . ? C3A H33A 0.9800 . ? C4A H41A 0.9800 . ? C4A H42A 0.9800 . ? C4A H43A 0.9800 . ? C6A C8A 1.536(5) . ? C6A C7A 1.545(5) . ? C6A H61A 1.0000 . ? C7A O2A 1.403(5) . ? C7A H71A 0.9900 . ? C7A H72A 0.9900 . ? O2A H5A 0.86(3) . ? O21A H51A 0.8497 . ? O1B C5B 1.225(4) . ? O2B C7B 1.426(5) . ? O2B H5B 0.84(3) . ? O3B C8B 1.251(4) . ? O4B C8B 1.266(4) . ? N1B C1B 1.492(4) . ? N1B H1B 0.91(3) . ? N1B H2B 0.96(3) . ? N1B H3B 0.93(3) . ? N2B C5B 1.325(4) . ? N2B C6B 1.454(5) . ? N2B H4B 0.82(3) . ? C1B C5B 1.533(5) . ? C1B C2B 1.538(5) . ? C1B H11B 1.0000 . ? C2B C4B 1.530(6) . ? C2B C3B 1.540(6) . ? C2B H21B 1.0000 . ? C3B H31B 0.9800 . ? C3B H32B 0.9800 . ? C3B H33B 0.9800 . ? C4B H41B 0.9800 . ? C4B H42B 0.9800 . ? C4B H43B 0.9800 . ? C6B C7B 1.528(5) . ? C6B C8B 1.535(5) . ? C6B H61B 1.0000 . ? C7B H71B 0.9900 . ? C7B H72B 0.9900 . ? O1C C5C 1.232(4) . ? O2C C7C 1.423(5) . ? O2C H5C 0.90(3) . ? O21C C7C 1.41(6) . ? O21C H5C 1.09(7) . ? O3C C8C 1.265(4) . ? O4C C8C 1.253(5) . ? N1C C1C 1.489(4) . ? N1C H1C 0.91(3) . ? N1C H2C 0.91(3) . ? N1C H3C 0.91(3) . ? N2C C5C 1.338(4) . ? N2C C6C 1.452(4) . ? N2C H4C 0.82(3) . ? C1C C5C 1.532(5) . ? C1C C2C 1.541(5) . ? C1C H11C 1.0000 . ? C2C C3C 1.523(6) . ? C2C C4C 1.526(5) . ? C2C H21C 1.0000 . ? C3C H31C 0.9800 . ? C3C H32C 0.9800 . ? C3C H33C 0.9800 . ? C4C H41C 0.9800 . ? C4C H42C 0.9800 . ? C4C H43C 0.9800 . ? C6C C8C 1.525(5) . ? C6C C7C 1.538(5) . ? C6C H61C 1.0000 . ? C7C H71C 0.9900 . ? C7C H72C 0.9900 . ? O1D C1D 1.430(5) . ? C1D C2D 1.529(5) . ? C2D F1D 1.320(5) . ? C2D F3D 1.320(5) . ? C2D F2D 1.320(5) . ? O1E C1E 1.430(5) . ? C1E C2E 1.529(5) . ? C2E F2E 1.319(5) . ? C2E F3E 1.319(5) . ? C2E F1E 1.320(5) . ? C2F F1F 1.321(5) . ? C2F F4F 1.321(5) . ? C2F F2F 1.321(5) . ? C2F F3F 1.322(5) . ? C2G F4G 1.321(5) . ? C2G F2G 1.322(5) . ? C2G F1G 1.322(5) . ? C2G F3G 1.322(5) . ? F1H F2H 1.31(4) . ? F2H F4H 1.26(6) . ? F3I F4H 1.26(7) . ? 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 C1A N1A H1A 122(3) . . ? C1A N1A H2A 118(3) . . ? H1A N1A H2A 98(4) . . ? C1A N1A H3A 104(2) . . ? H1A N1A H3A 107(4) . . ? H2A N1A H3A 107(4) . . ? C5A N2A C6A 120.9(3) . . ? C5A N2A H4A 119(3) . . ? C6A N2A H4A 119(3) . . ? N1A C1A C5A 105.4(3) . . ? N1A C1A C2A 111.2(3) . . ? C5A C1A C2A 113.5(3) . . ? N1A C1A H11A 108.9 . . ? C5A C1A H11A 108.9 . . ? C2A C1A H11A 108.9 . . ? C3A C2A C4A 112.3(3) . . ? C3A C2A C1A 114.0(3) . . ? C4A C2A C1A 110.4(3) . . ? C3A C2A H21A 106.5 . . ? C4A C2A H21A 106.5 . . ? C1A C2A H21A 106.5 . . ? C2A C3A H31A 109.5 . . ? C2A C3A H32A 109.5 . . ? H31A C3A H32A 109.5 . . ? C2A C3A H33A 109.5 . . ? H31A C3A H33A 109.5 . . ? H32A C3A H33A 109.5 . . ? C2A C4A H41A 109.5 . . ? C2A C4A H42A 109.5 . . ? H41A C4A H42A 109.5 . . ? C2A C4A H43A 109.5 . . ? H41A C4A H43A 109.5 . . ? H42A C4A H43A 109.5 . . ? O1A C5A N2A 124.1(3) . . ? O1A C5A C1A 119.1(3) . . ? N2A C5A C1A 116.8(3) . . ? N2A C6A C8A 109.7(3) . . ? N2A C6A C7A 111.6(3) . . ? C8A C6A C7A 110.0(3) . . ? N2A C6A H61A 108.5 . . ? C8A C6A H61A 108.5 . . ? C7A C6A H61A 108.5 . . ? O2A C7A C6A 112.8(3) . . ? O2A C7A H71A 109.0 . . ? C6A C7A H71A 109.0 . . ? O2A C7A H72A 109.0 . . ? C6A C7A H72A 109.0 . . ? H71A C7A H72A 107.8 . . ? C7A O2A H5A 101(3) . . ? O3A C8A O4A 126.0(3) . . ? O3A C8A C6A 117.3(3) . . ? O4A C8A C6A 116.7(3) . . ? C7B O2B H5B 106(3) . . ? C1B N1B H1B 117(3) . . ? C1B N1B H2B 109(3) . . ? H1B N1B H2B 102(4) . . ? C1B N1B H3B 102(3) . . ? H1B N1B H3B 119(4) . . ? H2B N1B H3B 108(4) . . ? C5B N2B C6B 121.5(3) . . ? C5B N2B H4B 118(3) . . ? C6B N2B H4B 120(3) . . ? N1B C1B C5B 106.2(3) . . ? N1B C1B C2B 112.8(3) . . ? C5B C1B C2B 112.3(3) . . ? N1B C1B H11B 108.5 . . ? C5B C1B H11B 108.5 . . ? C2B C1B H11B 108.5 . . ? C4B C2B C1B 110.3(4) . . ? C4B C2B C3B 113.1(3) . . ? C1B C2B C3B 112.1(3) . . ? C4B C2B H21B 107.0 . . ? C1B C2B H21B 107.0 . . ? C3B C2B H21B 107.0 . . ? C2B C3B H31B 109.5 . . ? C2B C3B H32B 109.5 . . ? H31B C3B H32B 109.5 . . ? C2B C3B H33B 109.5 . . ? H31B C3B H33B 109.5 . . ? H32B C3B H33B 109.5 . . ? C2B C4B H41B 109.5 . . ? C2B C4B H42B 109.5 . . ? H41B C4B H42B 109.5 . . ? C2B C4B H43B 109.5 . . ? H41B C4B H43B 109.5 . . ? H42B C4B H43B 109.5 . . ? O1B C5B N2B 125.1(3) . . ? O1B C5B C1B 120.5(3) . . ? N2B C5B C1B 114.4(3) . . ? N2B C6B C7B 109.5(3) . . ? N2B C6B C8B 112.8(3) . . ? C7B C6B C8B 113.0(3) . . ? N2B C6B H61B 107.1 . . ? C7B C6B H61B 107.1 . . ? C8B C6B H61B 107.1 . . ? O2B C7B C6B 111.3(3) . . ? O2B C7B H71B 109.4 . . ? C6B C7B H71B 109.4 . . ? O2B C7B H72B 109.4 . . ? C6B C7B H72B 109.4 . . ? H71B C7B H72B 108.0 . . ? O3B C8B O4B 125.1(3) . . ? O3B C8B C6B 120.5(3) . . ? O4B C8B C6B 114.4(3) . . ? C7C O2C H5C 103(3) . . ? C7C O21C H5C 94(5) . . ? C1C N1C H1C 110(3) . . ? C1C N1C H2C 117(3) . . ? H1C N1C H2C 113(4) . . ? C1C N1C H3C 123(3) . . ? H1C N1C H3C 89(4) . . ? H2C N1C H3C 102(4) . . ? C5C N2C C6C 118.0(3) . . ? C5C N2C H4C 119(3) . . ? C6C N2C H4C 123(3) . . ? N1C C1C C5C 105.9(3) . . ? N1C C1C C2C 112.6(3) . . ? C5C C1C C2C 111.9(3) . . ? N1C C1C H11C 108.8 . . ? C5C C1C H11C 108.8 . . ? C2C C1C H11C 108.8 . . ? C3C C2C C4C 111.9(3) . . ? C3C C2C C1C 112.9(3) . . ? C4C C2C C1C 110.4(3) . . ? C3C C2C H21C 107.1 . . ? C4C C2C H21C 107.1 . . ? C1C C2C H21C 107.1 . . ? C2C C3C H31C 109.5 . . ? C2C C3C H32C 109.5 . . ? H31C C3C H32C 109.5 . . ? C2C C3C H33C 109.5 . . ? H31C C3C H33C 109.5 . . ? H32C C3C H33C 109.5 . . ? C2C C4C H41C 109.5 . . ? C2C C4C H42C 109.5 . . ? H41C C4C H42C 109.5 . . ? C2C C4C H43C 109.5 . . ? H41C C4C H43C 109.5 . . ? H42C C4C H43C 109.5 . . ? O1C C5C N2C 123.0(3) . . ? O1C C5C C1C 120.6(3) . . ? N2C C5C C1C 116.3(3) . . ? N2C C6C C8C 111.8(3) . . ? N2C C6C C7C 112.6(3) . . ? C8C C6C C7C 110.8(3) . . ? N2C C6C H61C 107.1 . . ? C8C C6C H61C 107.1 . . ? C7C C6C H61C 107.1 . . ? O21C C7C O2C 47(3) . . ? O21C C7C C6C 125(3) . . ? O2C C7C C6C 108.1(3) . . ? O21C C7C H71C 124.1 . . ? O2C C7C H71C 110.1 . . ? C6C C7C H71C 110.1 . . ? O21C C7C H72C 63.3 . . ? O2C C7C H72C 110.1 . . ? C6C C7C H72C 110.1 . . ? H71C C7C H72C 108.4 . . ? O4C C8C O3C 125.8(3) . . ? O4C C8C C6C 116.3(3) . . ? O3C C8C C6C 117.9(3) . . ? O1D C1D C2D 112.5(8) . . ? F1D C2D F3D 110.3(8) . . ? F1D C2D F2D 109.6(8) . . ? F3D C2D F2D 110.0(8) . . ? F1D C2D C1D 109.0(7) . . ? F3D C2D C1D 109.0(8) . . ? F2D C2D C1D 108.9(7) . . ? O1E C1E C2E 112.5(9) . . ? F2E C2E F3E 109.8(8) . . ? F2E C2E F1E 109.9(8) . . ? F3E C2E F1E 110.0(8) . . ? F2E C2E C1E 109.0(8) . . ? F3E C2E C1E 109.2(8) . . ? F1E C2E C1E 108.9(8) . . ? F1F C2F F4F 109.6(8) . . ? F1F C2F F2F 109.4(8) . . ? F4F C2F F2F 109.5(8) . . ? F1F C2F F3F 109.5(8) . . ? F4F C2F F3F 109.4(8) . . ? F2F C2F F3F 109.5(8) . . ? F4G C2G F2G 109.7(8) . . ? F4G C2G F1G 109.2(8) . . ? F2G C2G F1G 109.4(8) . . ? F4G C2G F3G 109.4(8) . . ? F2G C2G F3G 109.5(8) . . ? F1G C2G F3G 109.6(8) . . ? F4H F2H F1H 160(5) . . ? F3I F4H F2H 113(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 N1A C1A C2A C3A 60.8(4) . . . . ? C5A C1A C2A C3A -57.8(4) . . . . ? N1A C1A C2A C4A -66.7(4) . . . . ? C5A C1A C2A C4A 174.7(3) . . . . ? C6A N2A C5A O1A -2.0(5) . . . . ? C6A N2A C5A C1A 177.4(3) . . . . ? N1A C1A C5A O1A -19.7(4) . . . . ? C2A C1A C5A O1A 102.2(4) . . . . ? N1A C1A C5A N2A 160.9(3) . . . . ? C2A C1A C5A N2A -77.2(4) . . . . ? C5A N2A C6A C8A -137.5(3) . . . . ? C5A N2A C6A C7A 100.4(4) . . . . ? N2A C6A C7A O2A -67.0(4) . . . . ? C8A C6A C7A O2A 171.0(3) . . . . ? N2A C6A C8A O3A -50.0(4) . . . . ? C7A C6A C8A O3A 73.1(4) . . . . ? N2A C6A C8A O4A 131.4(3) . . . . ? C7A C6A C8A O4A -105.5(4) . . . . ? N1B C1B C2B C4B -75.5(4) . . . . ? C5B C1B C2B C4B 164.6(3) . . . . ? N1B C1B C2B C3B 51.6(4) . . . . ? C5B C1B C2B C3B -68.4(4) . . . . ? C6B N2B C5B O1B 3.9(6) . . . . ? C6B N2B C5B C1B -178.0(3) . . . . ? N1B C1B C5B O1B -21.6(4) . . . . ? C2B C1B C5B O1B 102.1(4) . . . . ? N1B C1B C5B N2B 160.2(3) . . . . ? C2B C1B C5B N2B -76.1(4) . . . . ? C5B N2B C6B C7B 97.2(4) . . . . ? C5B N2B C6B C8B -136.1(3) . . . . ? N2B C6B C7B O2B 58.3(4) . . . . ? C8B C6B C7B O2B -68.2(4) . . . . ? N2B C6B C8B O3B -3.9(5) . . . . ? C7B C6B C8B O3B 120.9(4) . . . . ? N2B C6B C8B O4B 174.9(3) . . . . ? C7B C6B C8B O4B -60.3(4) . . . . ? N1C C1C C2C C3C 47.7(4) . . . . ? C5C C1C C2C C3C -71.5(4) . . . . ? N1C C1C C2C C4C -78.4(4) . . . . ? C5C C1C C2C C4C 162.4(3) . . . . ? C6C N2C C5C O1C -6.4(5) . . . . ? C6C N2C C5C C1C 171.1(3) . . . . ? N1C C1C C5C O1C -22.7(4) . . . . ? C2C C1C C5C O1C 100.3(4) . . . . ? N1C C1C C5C N2C 159.7(3) . . . . ? C2C C1C C5C N2C -77.3(4) . . . . ? C5C N2C C6C C8C -159.4(3) . . . . ? C5C N2C C6C C7C 75.1(4) . . . . ? N2C C6C C7C O21C 177(3) . . . . ? C8C C6C C7C O21C 51(3) . . . . ? N2C C6C C7C O2C -133.6(3) . . . . ? C8C C6C C7C O2C 100.4(3) . . . . ? N2C C6C C8C O4C 152.6(3) . . . . ? C7C C6C C8C O4C -80.9(4) . . . . ? N2C C6C C8C O3C -29.3(4) . . . . ? C7C C6C C8C O3C 97.2(4) . . . . ? O1D C1D C2D F1D 60(5) . . . . ? O1D C1D C2D F3D -61(5) . . . . ? O1D C1D C2D F2D 179(5) . . . . ? O1E C1E C2E F2E -61(8) . . . . ? O1E C1E C2E F3E 59(8) . . . . ? O1E C1E C2E F1E 179(8) . . . . ? F1H F2H F4H F3I 168(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.274 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.054 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_publ_flag _geom_hbond_site_symmetry_A N1A H1A O4B 0.92(3) 1.82(3) 2.727(4) 168(3) y 1_645 N1A H2A O3B 0.92(3) 1.97(3) 2.887(4) 172(3) y 2_647 N1A H3A O2C 0.97(3) 2.19(3) 3.000(5) 139(3) y 2_646 N1A H3A O1C 0.97(3) 2.34(4) 2.951(4) 120(3) y 2_646 N2A H4A O4A 0.85(3) 2.16(3) 2.985(4) 165(3) y 2_646 O2A H5A O3C 0.86(3) 2.05(3) 2.873(5) 163(5) y 1_655 C1A H11A O1C 1.00 2.33 2.927(4) 117 y 2_646 N1B H1B O4C 0.91(3) 1.86(3) 2.756(4) 167(3) y 2_546 N1B H2B O3C 0.96(3) 1.95(3) 2.799(4) 146(3) y 1_555 N1B H3B O1A 0.93(3) 1.88(3) 2.779(4) 161(3) y 1_455 N2B H4B O4B 0.82(3) 2.09(3) 2.890(4) 165(3) y 2_547 O2B H5B O3B 0.84(3) 1.99(3) 2.801(4) 161(3) y 2_547 N1C H1C O1B 0.91(2) 2.02(3) 2.739(4) 135(3) y 2_546 N1C H2C O4A 0.91(3) 1.81(3) 2.708(4) 169(3) y 2_646 N1C H3C O3A 0.91(3) 1.89(3) 2.744(4) 157(3) y 1_555 N2C H4C O4C 0.82(3) 2.25(3) 3.032(3) 160(3) y 2_546 O2C H5C O2B 0.90(3) 1.86(3) 2.743(4) 170(4) y 1_554 data_VS-tfe20 _database_code_depnum_ccdc_archive 'CCDC 283668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Valyl-L-serine trifluoroethanol solvate ; _chemical_name_common 'L-Valyl-L-serine trifluoroethanol solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8.55 H15.94 N2 O4.08' _chemical_formula_weight 212.13 _chemical_absolute_configuration 'known for the purchased material' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.0999(14) _cell_length_b 9.8140(10) _cell_length_c 14.2142(14) _cell_angle_alpha 90.00 _cell_angle_beta 116.140(2) _cell_angle_gamma 90.00 _cell_volume 1765.7(3) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4172 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 26.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8658 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 105(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_% none _diffrn_reflns_number 10720 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3835 _reflns_number_gt 3118 _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 three sets of exposures with the detector set at 2\q = 29\%, 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^)+(0.0444P)^2^+0.3921P] 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 3835 _refine_ls_number_parameters 468 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.005 _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 0.80315(17) 0.5360(3) 0.70319(17) 0.0303(5) Uani 1 1 d . . . O3A O 0.45556(17) 0.5656(3) 0.40844(18) 0.0299(5) Uani 1 1 d . A . O4A O 0.52489(17) 0.7746(3) 0.44829(18) 0.0278(5) Uani 1 1 d . A . N1A N 0.8270(2) 0.3237(4) 0.8191(2) 0.0234(6) Uani 1 1 d D A . H1A H 0.836(3) 0.250(3) 0.861(3) 0.035 Uiso 1 1 d D . . H2A H 0.858(3) 0.401(3) 0.859(3) 0.035 Uiso 1 1 d D . . H3A H 0.874(2) 0.307(4) 0.785(3) 0.035 Uiso 1 1 d D . . N2A N 0.6447(2) 0.4733(4) 0.5730(2) 0.0216(6) Uani 1 1 d D . . H4A H 0.591(2) 0.421(3) 0.552(3) 0.026 Uiso 1 1 d D . . C1A C 0.7166(2) 0.3472(4) 0.7375(2) 0.0203(6) Uani 1 1 d . . . H11A H 0.6909 0.2626 0.6944 0.024 Uiso 1 1 calc R A . C2A C 0.6416(3) 0.3808(4) 0.7868(2) 0.0244(7) Uani 1 1 d . A . H21A H 0.5706 0.3981 0.7274 0.029 Uiso 1 1 calc R . . C3A C 0.6718(3) 0.5094(5) 0.8532(3) 0.0463(11) Uani 1 1 d . . . H31A H 0.6818 0.5844 0.8130 0.069 Uiso 1 1 calc R A . H32A H 0.7377 0.4937 0.9166 0.069 Uiso 1 1 calc R . . H33A H 0.6154 0.5329 0.8730 0.069 Uiso 1 1 calc R . . C4A C 0.6295(3) 0.2573(5) 0.8461(3) 0.0440(10) Uani 1 1 d . . . H41A H 0.5761 0.2768 0.8708 0.066 Uiso 1 1 calc R A . H42A H 0.6972 0.2377 0.9062 0.066 Uiso 1 1 calc R . . H43A H 0.6073 0.1782 0.7992 0.066 Uiso 1 1 calc R . . C5A C 0.7251(2) 0.4606(4) 0.6683(2) 0.0206(7) Uani 1 1 d . A . C6A C 0.6425(2) 0.5839(4) 0.5025(2) 0.0211(7) Uani 0.868(8) 1 d P A 1 H61A H 0.6927 0.6565 0.5454 0.025 Uiso 1 1 calc R A 1 C7A C 0.6765(3) 0.5354(4) 0.4198(3) 0.0301(8) Uani 0.868(8) 1 d PD A 1 H71A H 0.6315 0.4578 0.3810 0.036 Uiso 0.868(8) 1 calc PR A 1 H72A H 0.6652 0.6100 0.3691 0.036 Uiso 0.868(8) 1 calc PR A 1 O2A O 0.7835(2) 0.4948(4) 0.4633(2) 0.0350(10) Uani 0.868(8) 1 d PD A 1 H5A H 0.811(3) 0.561(4) 0.449(4) 0.052 Uiso 0.868(8) 1 d PD A 1 C61A C 0.6425(2) 0.5839(4) 0.5025(2) 0.0211(7) Uani 0.132(8) 1 d P A 2 C71A C 0.6765(3) 0.5354(4) 0.4198(3) 0.0301(8) Uani 0.132(8) 1 d P A 2 H73A H 0.7356 0.4705 0.4543 0.036 Uiso 0.132(8) 1 calc PR A 2 H74A H 0.6169 0.4834 0.3665 0.036 Uiso 0.132(8) 1 calc PR A 2 O21A O 0.705(2) 0.620(3) 0.3730(19) 0.061(8) Uiso 0.132(8) 1 d P A 2 C8A C 0.5310(2) 0.6459(4) 0.4491(2) 0.0217(7) Uani 1 1 d . . . O1B O -0.11415(17) 0.8353(3) 0.69131(16) 0.0275(5) Uani 1 1 d . . . O2B O -0.1458(2) 0.7745(4) 0.99190(19) 0.0332(6) Uani 1 1 d D . . H5B H -0.118(3) 0.704(3) 0.981(3) 0.050 Uiso 1 1 d D . . O3B O 0.05702(17) 1.0217(3) 1.02021(18) 0.0318(6) Uani 1 1 d . . . O4B O -0.09543(17) 1.1324(3) 0.97443(16) 0.0249(5) Uani 1 1 d . . . N1B N -0.0237(2) 0.6104(4) 0.6696(2) 0.0215(6) Uani 1 1 d D . . H1B H 0.020(3) 0.544(3) 0.665(3) 0.032 Uiso 1 1 d D . . H2B H -0.043(3) 0.675(3) 0.618(2) 0.032 Uiso 1 1 d D . . H3B H -0.088(2) 0.580(4) 0.670(3) 0.032 Uiso 1 1 d D . . N2B N -0.0349(2) 0.8276(4) 0.8691(2) 0.0237(6) Uani 1 1 d D . . H4B H 0.010(2) 0.786(4) 0.925(2) 0.028 Uiso 1 1 d D . . C1B C 0.0263(2) 0.6738(4) 0.7752(2) 0.0211(7) Uani 1 1 d . . . H11B H 0.0309 0.6037 0.8281 0.025 Uiso 1 1 calc R . . C2B C 0.1379(3) 0.7279(5) 0.8044(3) 0.0325(8) Uani 1 1 d . . . H21B H 0.1587 0.7844 0.8690 0.039 Uiso 1 1 calc R . . C3B C 0.1415(3) 0.8220(5) 0.7195(3) 0.0457(10) Uani 1 1 d . . . H31B H 0.0858 0.8909 0.7003 0.069 Uiso 1 1 calc R . . H32B H 0.1305 0.7679 0.6575 0.069 Uiso 1 1 calc R . . H33B H 0.2105 0.8670 0.7465 0.069 Uiso 1 1 calc R . . C4B C 0.2167(3) 0.6111(5) 0.8326(3) 0.0470(10) Uani 1 1 d . . . H41B H 0.2135 0.5569 0.8890 0.070 Uiso 1 1 calc R . . H42B H 0.2882 0.6480 0.8560 0.070 Uiso 1 1 calc R . . H43B H 0.1993 0.5534 0.7709 0.070 Uiso 1 1 calc R . . C5B C -0.0484(2) 0.7865(4) 0.7750(2) 0.0202(7) Uani 1 1 d . . . C6B C -0.1025(2) 0.9300(4) 0.8821(2) 0.0229(7) Uani 1 1 d . . . H61B H -0.1382 0.9802 0.8142 0.027 Uiso 1 1 calc R . . C7B C -0.1887(3) 0.8604(4) 0.9025(3) 0.0287(8) Uani 1 1 d D . . H71B H -0.2335 0.9308 0.9130 0.034 Uiso 1 1 calc R . . H72B H -0.2342 0.8056 0.8404 0.034 Uiso 1 1 calc R . . C8B C -0.0402(3) 1.0352(4) 0.9671(2) 0.0219(7) Uani 1 1 d . . . O1C O 0.19401(18) 0.6580(3) 0.36200(18) 0.0288(5) Uani 1 1 d . . . O3C O -0.08482(17) 0.7225(3) 0.46971(17) 0.0270(5) Uani 1 1 d . B . O4C O -0.07413(18) 0.9296(3) 0.40861(18) 0.0269(5) Uani 1 1 d . B . N1C N 0.3051(2) 0.4382(4) 0.4497(2) 0.0205(6) Uani 1 1 d D B . H1C H 0.262(3) 0.393(3) 0.390(2) 0.031 Uiso 1 1 d D . . H2C H 0.359(2) 0.380(3) 0.493(2) 0.031 Uiso 1 1 d D . . H3C H 0.339(3) 0.506(3) 0.435(3) 0.031 Uiso 1 1 d D . . N2C N 0.0809(2) 0.6331(4) 0.4336(2) 0.0220(6) Uani 1 1 d D . . H4C H 0.071(3) 0.588(3) 0.477(2) 0.026 Uiso 1 1 d D . . C1C C 0.2386(2) 0.4911(4) 0.4988(2) 0.0200(6) Uani 1 1 d . . . H11C H 0.1928 0.4155 0.5026 0.024 Uiso 1 1 calc R B . C2C C 0.3045(3) 0.5469(4) 0.6098(3) 0.0284(7) Uani 1 1 d . B . H21C H 0.2555 0.6008 0.6291 0.034 Uiso 1 1 calc R . . C3C C 0.3920(3) 0.6442(5) 0.6161(3) 0.0430(10) Uani 1 1 d . . . H31C H 0.4255 0.6856 0.6859 0.064 Uiso 1 1 calc R B . H32C H 0.3616 0.7158 0.5631 0.064 Uiso 1 1 calc R . . H33C H 0.4450 0.5934 0.6032 0.064 Uiso 1 1 calc R . . C4C C 0.3478(3) 0.4315(5) 0.6889(3) 0.0330(8) Uani 1 1 d . . . H41C H 0.3893 0.4696 0.7590 0.050 Uiso 1 1 calc R B . H42C H 0.3930 0.3728 0.6701 0.050 Uiso 1 1 calc R . . H43C H 0.2891 0.3779 0.6887 0.050 Uiso 1 1 calc R . . C5C C 0.1683(2) 0.6007(4) 0.4246(2) 0.0221(7) Uani 1 1 d . B . C6C C 0.0194(2) 0.7502(4) 0.3757(2) 0.0205(7) Uani 0.954(6) 1 d PD B 1 H61C H 0.0707 0.8240 0.3817 0.025 Uiso 1 1 calc R B 1 C7C C -0.0458(3) 0.7203(4) 0.2581(2) 0.0273(7) Uani 0.954(6) 1 d PD B 1 H71C H -0.0226 0.6334 0.2395 0.033 Uiso 0.954(6) 1 calc PR B 1 H72C H -0.1217 0.7125 0.2410 0.033 Uiso 0.954(6) 1 calc PR B 1 O2C O -0.0298(2) 0.8294(3) 0.20128(19) 0.0370(9) Uani 0.954(6) 1 d PD B 1 H5C H -0.076(3) 0.815(5) 0.136(2) 0.056 Uiso 0.954(6) 1 d PD B 1 C61C C 0.0194(2) 0.7502(4) 0.3757(2) 0.0205(7) Uani 0.046(6) 1 d PD B 2 C71C C -0.0458(3) 0.7203(4) 0.2581(2) 0.0273(7) Uani 0.046(6) 1 d PD B 2 H73C H 0.0016 0.6948 0.2262 0.033 Uiso 0.046(6) 1 calc PR B 2 H74C H -0.0951 0.6438 0.2482 0.033 Uiso 0.046(6) 1 calc PR B 2 O21C O -0.103(4) 0.840(2) 0.2100(11) 0.050 Uiso 0.046(6) 1 d PD B 2 C8C C -0.0516(2) 0.8053(4) 0.4229(2) 0.0203(7) Uani 1 1 d . . . O1W O 0.584(4) 0.842(6) 0.705(4) 0.07(2) Uiso 0.074(11) 1 d P . . O1D O 0.480(4) 0.909(6) 0.855(4) 0.200 Uiso 0.184(13) 1 d P . . C1D C 0.534(3) 0.816(4) 0.942(3) 0.200 Uiso 0.39(2) 1 d P . . C2D C 0.484(3) 0.655(5) 0.952(3) 0.200 Uiso 0.33(2) 1 d P . . C3D C 0.486(4) 0.466(5) 0.983(4) 0.200 Uiso 0.32(2) 1 d P . . C4D C 0.364(3) 0.262(4) 0.949(3) 0.200 Uiso 0.400(19) 1 d P . . C5D C 0.391(4) 0.101(6) 0.872(4) 0.200 Uiso 0.247(19) 1 d P . . 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 0.0218(12) 0.0365(13) 0.0270(12) 0.0058(11) 0.0054(10) -0.0075(11) O3A 0.0204(12) 0.0277(12) 0.0381(13) 0.0014(11) 0.0095(10) -0.0062(10) O4A 0.0194(11) 0.0212(11) 0.0367(14) 0.0035(10) 0.0066(10) 0.0022(10) N1A 0.0205(14) 0.0254(14) 0.0233(14) 0.0038(12) 0.0085(12) 0.0021(12) N2A 0.0172(13) 0.0173(13) 0.0270(15) 0.0032(11) 0.0066(12) -0.0021(11) C1A 0.0173(15) 0.0210(15) 0.0192(15) -0.0001(13) 0.0049(12) -0.0006(13) C2A 0.0201(16) 0.0299(17) 0.0238(17) -0.0016(14) 0.0102(14) -0.0013(14) C3A 0.038(2) 0.050(3) 0.058(3) -0.025(2) 0.028(2) -0.0066(19) C4A 0.041(2) 0.055(3) 0.047(2) 0.011(2) 0.0289(19) -0.002(2) C5A 0.0189(16) 0.0190(15) 0.0257(17) 0.0014(13) 0.0114(14) 0.0011(13) C6A 0.0208(16) 0.0177(15) 0.0256(16) 0.0048(13) 0.0109(14) 0.0013(13) C7A 0.0286(18) 0.0298(18) 0.0357(19) 0.0052(16) 0.0176(16) 0.0007(15) O2A 0.0270(17) 0.0355(17) 0.048(2) 0.0073(14) 0.0221(14) 0.0058(13) C61A 0.0208(16) 0.0177(15) 0.0256(16) 0.0048(13) 0.0109(14) 0.0013(13) C71A 0.0286(18) 0.0298(18) 0.0357(19) 0.0052(16) 0.0176(16) 0.0007(15) C8A 0.0194(16) 0.0253(16) 0.0193(15) 0.0046(14) 0.0077(13) 0.0001(14) O1B 0.0285(12) 0.0305(12) 0.0186(11) 0.0020(10) 0.0058(10) 0.0069(10) O2B 0.0387(14) 0.0296(12) 0.0326(13) 0.0013(11) 0.0169(11) 0.0007(12) O3B 0.0227(12) 0.0270(12) 0.0321(13) -0.0023(11) -0.0003(11) 0.0025(10) O4B 0.0299(12) 0.0197(11) 0.0215(11) -0.0018(9) 0.0082(10) 0.0037(10) N1B 0.0240(15) 0.0208(14) 0.0212(14) -0.0004(11) 0.0115(12) 0.0006(12) N2B 0.0267(15) 0.0223(13) 0.0179(13) 0.0027(12) 0.0061(11) 0.0084(12) C1B 0.0229(16) 0.0225(15) 0.0156(15) 0.0009(12) 0.0066(13) 0.0028(13) C2B 0.0210(17) 0.0379(19) 0.0337(19) -0.0110(17) 0.0076(15) -0.0011(16) C3B 0.032(2) 0.043(2) 0.066(3) 0.002(2) 0.026(2) -0.0106(19) C4B 0.0258(19) 0.062(3) 0.046(2) -0.006(2) 0.0096(17) 0.007(2) C5B 0.0211(16) 0.0181(14) 0.0205(16) -0.0004(13) 0.0084(13) -0.0012(13) C6B 0.0240(17) 0.0202(15) 0.0201(16) 0.0004(13) 0.0057(13) 0.0062(13) C7B 0.0256(17) 0.0246(17) 0.0299(18) -0.0012(14) 0.0069(15) 0.0007(14) C8B 0.0282(18) 0.0182(15) 0.0181(15) 0.0052(13) 0.0090(14) 0.0009(14) O1C 0.0285(12) 0.0283(12) 0.0363(13) 0.0117(11) 0.0204(11) 0.0069(10) O3C 0.0293(13) 0.0272(12) 0.0301(12) 0.0052(11) 0.0182(10) 0.0026(10) O4C 0.0308(13) 0.0211(11) 0.0354(13) 0.0028(10) 0.0206(11) 0.0048(10) N1C 0.0180(13) 0.0183(13) 0.0245(14) 0.0001(11) 0.0088(12) -0.0008(11) N2C 0.0234(14) 0.0215(14) 0.0250(14) 0.0067(12) 0.0142(12) 0.0032(11) C1C 0.0174(15) 0.0204(15) 0.0242(16) -0.0004(13) 0.0108(13) -0.0003(12) C2C 0.0286(18) 0.0319(18) 0.0239(17) -0.0027(15) 0.0108(15) 0.0055(15) C3C 0.046(2) 0.040(2) 0.033(2) -0.0116(18) 0.0078(17) -0.0129(19) C4C 0.0286(18) 0.042(2) 0.0261(18) 0.0051(16) 0.0096(15) 0.0056(17) C5C 0.0213(16) 0.0214(15) 0.0248(16) -0.0003(13) 0.0113(14) 0.0007(13) C6C 0.0216(16) 0.0182(15) 0.0225(16) 0.0044(13) 0.0106(13) 0.0044(13) C7C 0.0328(19) 0.0251(17) 0.0258(17) -0.0001(15) 0.0143(15) -0.0012(15) O2C 0.0460(19) 0.0372(15) 0.0218(13) 0.0069(12) 0.0094(12) -0.0076(13) C61C 0.0216(16) 0.0182(15) 0.0225(16) 0.0044(13) 0.0106(13) 0.0044(13) C71C 0.0328(19) 0.0251(17) 0.0258(17) -0.0001(15) 0.0143(15) -0.0012(15) C8C 0.0156(15) 0.0240(17) 0.0189(15) 0.0005(13) 0.0055(12) 0.0016(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C5A 1.234(4) . ? O3A C8A 1.243(4) . ? O4A C8A 1.265(4) . ? N1A C1A 1.494(4) . ? N1A H1A 0.91(3) . ? N1A H2A 0.93(3) . ? N1A H3A 0.99(2) . ? N2A C5A 1.335(4) . ? N2A C6A 1.469(4) . ? N2A H4A 0.85(2) . ? C1A C5A 1.525(4) . ? C1A C2A 1.539(4) . ? C1A H11A 1.0000 . ? C2A C3A 1.520(5) . ? C2A C4A 1.528(5) . ? C2A H21A 1.0000 . ? C3A H31A 0.9800 . ? C3A H32A 0.9800 . ? C3A H33A 0.9800 . ? C4A H41A 0.9800 . ? C4A H42A 0.9800 . ? C4A H43A 0.9800 . ? C6A C7A 1.527(5) . ? C6A C8A 1.539(4) . ? C6A H61A 1.0000 . ? C7A O2A 1.412(4) . ? C7A H71A 0.9900 . ? C7A H72A 0.9900 . ? O2A H5A 0.82(3) . ? O1B C5B 1.238(4) . ? O2B C7B 1.419(4) . ? O2B H5B 0.83(3) . ? O3B C8B 1.247(4) . ? O4B C8B 1.264(4) . ? N1B C1B 1.485(4) . ? N1B H1B 0.92(2) . ? N1B H2B 0.91(2) . ? N1B H3B 0.95(2) . ? N2B C5B 1.328(4) . ? N2B C6B 1.452(4) . ? N2B H4B 0.86(2) . ? C1B C5B 1.526(4) . ? C1B C2B 1.535(5) . ? C1B H11B 1.0000 . ? C2B C4B 1.522(5) . ? C2B C3B 1.537(6) . ? C2B H21B 1.0000 . ? C3B H31B 0.9800 . ? C3B H32B 0.9800 . ? C3B H33B 0.9800 . ? C4B H41B 0.9800 . ? C4B H42B 0.9800 . ? C4B H43B 0.9800 . ? C6B C7B 1.530(5) . ? C6B C8B 1.537(4) . ? C6B H61B 1.0000 . ? C7B H71B 0.9900 . ? C7B H72B 0.9900 . ? O1C C5C 1.235(4) . ? O3C C8C 1.263(4) . ? O4C C8C 1.254(4) . ? N1C C1C 1.487(4) . ? N1C H1C 0.91(2) . ? N1C H2C 0.94(3) . ? N1C H3C 0.90(2) . ? N2C C5C 1.332(4) . ? N2C C6C 1.457(4) . ? N2C H4C 0.82(2) . ? C1C C5C 1.526(4) . ? C1C C2C 1.537(4) . ? C1C H11C 1.0000 . ? C2C C4C 1.521(5) . ? C2C C3C 1.532(5) . ? C2C H21C 1.0000 . ? C3C H31C 0.9800 . ? C3C H32C 0.9800 . ? C3C H33C 0.9800 . ? C4C H41C 0.9800 . ? C4C H42C 0.9800 . ? C4C H43C 0.9800 . ? C6C C8C 1.529(4) . ? C6C C7C 1.540(4) . ? C6C H61C 1.0000 . ? C7C O2C 1.418(4) . ? C7C H71C 0.9900 . ? C7C H72C 0.9900 . ? O2C H5C 0.88(3) . ? O21C H5C 1.29(6) . ? O1D C1D 1.46(6) . ? C1D C4D 1.67(4) 2_657 ? C1D C2D 1.76(6) . ? C1D C3D 1.90(6) 2_657 ? C2D C3D 1.91(7) . ? C3D C1D 1.90(6) 2_647 ? C4D C1D 1.67(4) 2_647 ? 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 C1A N1A H1A 115(2) . . ? C1A N1A H2A 113(2) . . ? H1A N1A H2A 111(3) . . ? C1A N1A H3A 110(2) . . ? H1A N1A H3A 105(3) . . ? H2A N1A H3A 102(3) . . ? C5A N2A C6A 121.0(3) . . ? C5A N2A H4A 122(2) . . ? C6A N2A H4A 117(2) . . ? N1A C1A C5A 105.2(2) . . ? N1A C1A C2A 111.7(2) . . ? C5A C1A C2A 113.7(3) . . ? N1A C1A H11A 108.7 . . ? C5A C1A H11A 108.7 . . ? C2A C1A H11A 108.7 . . ? C3A C2A C4A 112.6(3) . . ? C3A C2A C1A 113.6(3) . . ? C4A C2A C1A 110.3(3) . . ? C3A C2A H21A 106.6 . . ? C4A C2A H21A 106.6 . . ? C1A C2A H21A 106.6 . . ? C2A C3A H31A 109.5 . . ? C2A C3A H32A 109.5 . . ? H31A C3A H32A 109.5 . . ? C2A C3A H33A 109.5 . . ? H31A C3A H33A 109.5 . . ? H32A C3A H33A 109.5 . . ? C2A C4A H41A 109.5 . . ? C2A C4A H42A 109.5 . . ? H41A C4A H42A 109.5 . . ? C2A C4A H43A 109.5 . . ? H41A C4A H43A 109.5 . . ? H42A C4A H43A 109.5 . . ? O1A C5A N2A 124.1(3) . . ? O1A C5A C1A 119.2(3) . . ? N2A C5A C1A 116.7(3) . . ? N2A C6A C7A 112.1(3) . . ? N2A C6A C8A 109.8(2) . . ? C7A C6A C8A 110.1(3) . . ? N2A C6A H61A 108.3 . . ? C7A C6A H61A 108.3 . . ? C8A C6A H61A 108.3 . . ? O2A C7A C6A 112.8(3) . . ? O2A C7A H71A 109.0 . . ? C6A C7A H71A 109.0 . . ? O2A C7A H72A 109.0 . . ? C6A C7A H72A 109.0 . . ? H71A C7A H72A 107.8 . . ? C7A O2A H5A 101(3) . . ? O3A C8A O4A 126.0(3) . . ? O3A C8A C6A 117.2(3) . . ? O4A C8A C6A 116.7(3) . . ? C7B O2B H5B 112(3) . . ? C1B N1B H1B 110(2) . . ? C1B N1B H2B 111(2) . . ? H1B N1B H2B 114(3) . . ? C1B N1B H3B 99(2) . . ? H1B N1B H3B 116(3) . . ? H2B N1B H3B 106(3) . . ? C5B N2B C6B 121.8(3) . . ? C5B N2B H4B 120(2) . . ? C6B N2B H4B 118(2) . . ? N1B C1B C5B 106.4(2) . . ? N1B C1B C2B 113.1(3) . . ? C5B C1B C2B 112.0(3) . . ? N1B C1B H11B 108.4 . . ? C5B C1B H11B 108.4 . . ? C2B C1B H11B 108.4 . . ? C4B C2B C1B 110.7(3) . . ? C4B C2B C3B 112.7(3) . . ? C1B C2B C3B 112.3(3) . . ? C4B C2B H21B 106.9 . . ? C1B C2B H21B 106.9 . . ? C3B C2B H21B 106.9 . . ? C2B C3B H31B 109.5 . . ? C2B C3B H32B 109.5 . . ? H31B C3B H32B 109.5 . . ? C2B C3B H33B 109.5 . . ? H31B C3B H33B 109.5 . . ? H32B C3B H33B 109.5 . . ? C2B C4B H41B 109.5 . . ? C2B C4B H42B 109.5 . . ? H41B C4B H42B 109.5 . . ? C2B C4B H43B 109.5 . . ? H41B C4B H43B 109.5 . . ? H42B C4B H43B 109.5 . . ? O1B C5B N2B 124.4(3) . . ? O1B C5B C1B 120.4(3) . . ? N2B C5B C1B 115.2(3) . . ? N2B C6B C7B 109.6(3) . . ? N2B C6B C8B 112.7(3) . . ? C7B C6B C8B 112.2(3) . . ? N2B C6B H61B 107.4 . . ? C7B C6B H61B 107.4 . . ? C8B C6B H61B 107.4 . . ? O2B C7B C6B 112.0(3) . . ? O2B C7B H71B 109.2 . . ? C6B C7B H71B 109.2 . . ? O2B C7B H72B 109.2 . . ? C6B C7B H72B 109.2 . . ? H71B C7B H72B 107.9 . . ? O3B C8B O4B 125.7(3) . . ? O3B C8B C6B 119.9(3) . . ? O4B C8B C6B 114.4(3) . . ? C1C N1C H1C 108(2) . . ? C1C N1C H2C 114(2) . . ? H1C N1C H2C 109(3) . . ? C1C N1C H3C 112(2) . . ? H1C N1C H3C 110(3) . . ? H2C N1C H3C 104(3) . . ? C5C N2C C6C 118.7(3) . . ? C5C N2C H4C 115(3) . . ? C6C N2C H4C 127(3) . . ? N1C C1C C5C 105.9(2) . . ? N1C C1C C2C 112.6(3) . . ? C5C C1C C2C 111.9(3) . . ? N1C C1C H11C 108.8 . . ? C5C C1C H11C 108.8 . . ? C2C C1C H11C 108.8 . . ? C4C C2C C3C 111.7(3) . . ? C4C C2C C1C 111.0(3) . . ? C3C C2C C1C 112.9(3) . . ? C4C C2C H21C 106.9 . . ? C3C C2C H21C 106.9 . . ? C1C C2C H21C 106.9 . . ? C2C C3C H31C 109.5 . . ? C2C C3C H32C 109.5 . . ? H31C C3C H32C 109.5 . . ? C2C C3C H33C 109.5 . . ? H31C C3C H33C 109.5 . . ? H32C C3C H33C 109.5 . . ? C2C C4C H41C 109.5 . . ? C2C C4C H42C 109.5 . . ? H41C C4C H42C 109.5 . . ? C2C C4C H43C 109.5 . . ? H41C C4C H43C 109.5 . . ? H42C C4C H43C 109.5 . . ? O1C C5C N2C 122.5(3) . . ? O1C C5C C1C 120.8(3) . . ? N2C C5C C1C 116.7(3) . . ? N2C C6C C8C 111.9(2) . . ? N2C C6C C7C 112.6(2) . . ? C8C C6C C7C 110.6(2) . . ? N2C C6C H61C 107.1 . . ? C8C C6C H61C 107.1 . . ? C7C C6C H61C 107.1 . . ? O2C C7C C6C 107.8(3) . . ? O2C C7C H71C 110.2 . . ? C6C C7C H71C 110.2 . . ? O2C C7C H72C 110.2 . . ? C6C C7C H72C 110.2 . . ? H71C C7C H72C 108.5 . . ? C7C O2C H5C 104(3) . . ? O4C C8C O3C 125.8(3) . . ? O4C C8C C6C 116.2(3) . . ? O3C C8C C6C 118.0(3) . . ? O1D C1D C4D 155(4) . 2_657 ? O1D C1D C2D 123(4) . . ? C4D C1D C2D 82(3) 2_657 . ? O1D C1D C3D 81(3) . 2_657 ? C4D C1D C3D 91(3) 2_657 2_657 ? C2D C1D C3D 119(3) . 2_657 ? C1D C2D C3D 158(4) . . ? C1D C3D C2D 153(3) 2_647 . ? 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 N1A C1A C2A C3A 61.0(4) . . . . ? C5A C1A C2A C3A -57.9(4) . . . . ? N1A C1A C2A C4A -66.5(4) . . . . ? C5A C1A C2A C4A 174.6(3) . . . . ? C6A N2A C5A O1A -1.8(5) . . . . ? C6A N2A C5A C1A 176.6(3) . . . . ? N1A C1A C5A O1A -20.8(4) . . . . ? C2A C1A C5A O1A 101.7(3) . . . . ? N1A C1A C5A N2A 160.6(3) . . . . ? C2A C1A C5A N2A -76.9(3) . . . . ? C5A N2A C6A C7A 100.4(3) . . . . ? C5A N2A C6A C8A -136.9(3) . . . . ? N2A C6A C7A O2A -65.7(4) . . . . ? C8A C6A C7A O2A 171.8(3) . . . . ? N2A C6A C8A O3A -49.0(4) . . . . ? C7A C6A C8A O3A 74.9(3) . . . . ? N2A C6A C8A O4A 132.9(3) . . . . ? C7A C6A C8A O4A -103.2(3) . . . . ? N1B C1B C2B C4B -75.1(4) . . . . ? C5B C1B C2B C4B 164.8(3) . . . . ? N1B C1B C2B C3B 51.9(4) . . . . ? C5B C1B C2B C3B -68.3(4) . . . . ? C6B N2B C5B O1B 4.1(5) . . . . ? C6B N2B C5B C1B -177.4(3) . . . . ? N1B C1B C5B O1B -20.9(4) . . . . ? C2B C1B C5B O1B 103.1(3) . . . . ? N1B C1B C5B N2B 160.6(3) . . . . ? C2B C1B C5B N2B -75.4(3) . . . . ? C5B N2B C6B C7B 97.5(3) . . . . ? C5B N2B C6B C8B -136.8(3) . . . . ? N2B C6B C7B O2B 57.6(3) . . . . ? C8B C6B C7B O2B -68.4(3) . . . . ? N2B C6B C8B O3B -4.1(4) . . . . ? C7B C6B C8B O3B 120.2(3) . . . . ? N2B C6B C8B O4B 174.3(3) . . . . ? C7B C6B C8B O4B -61.4(3) . . . . ? N1C C1C C2C C4C -77.8(3) . . . . ? C5C C1C C2C C4C 163.0(3) . . . . ? N1C C1C C2C C3C 48.5(4) . . . . ? C5C C1C C2C C3C -70.7(4) . . . . ? C6C N2C C5C O1C -6.8(5) . . . . ? C6C N2C C5C C1C 171.2(3) . . . . ? N1C C1C C5C O1C -22.2(4) . . . . ? C2C C1C C5C O1C 100.9(3) . . . . ? N1C C1C C5C N2C 159.8(3) . . . . ? C2C C1C C5C N2C -77.2(3) . . . . ? C5C N2C C6C C8C -159.0(3) . . . . ? C5C N2C C6C C7C 75.8(4) . . . . ? N2C C6C C7C O2C -132.7(3) . . . . ? C8C C6C C7C O2C 101.3(3) . . . . ? N2C C6C C8C O4C 152.7(3) . . . . ? C7C C6C C8C O4C -80.9(3) . . . . ? N2C C6C C8C O3C -29.4(4) . . . . ? C7C C6C C8C O3C 97.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.262 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.047 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_publ_flag _geom_hbond_site_symmetry_A N1A H1A O4B 0.91(3) 1.87(3) 2.732(3) 158(3) y 1_645 N1A H2A O3B 0.93(3) 1.99(3) 2.894(4) 161(3) y 2_647 N1A H3A O2C 0.99(2) 2.13(3) 2.998(4) 145(3) y 2_646 N1A H3A O1C 0.99(3) 2.38(3) 2.947(4) 116(3) y 2_646 N2A H4A O4A 0.85(2) 2.18(3) 2.996(3) 161(3) y 2_646 O2A H5A O3C 0.82(3) 2.10(3) 2.882(4) 159(5) y 1_655 C1A H11A O1C 1.00 2.34 2.934(4) 117 y 2_646 N1B H1B O4C 0.92(2) 1.91(3) 2.764(3) 154(3) y 2_546 N1B H2B O3C 0.91(2) 1.98(3) 2.805(3) 149(3) y 1_555 N1B H3B O1A 0.95(2) 1.85(3) 2.783(4) 166(3) y 1_455 N2B H4B O4B 0.86(2) 2.06(3) 2.896(3) 161(3) y 2_547 O2B H5B O3B 0.83(3) 1.99(3) 2.818(4) 169(3) y 2_547 N1C H1C O1B 0.91(2) 1.96(3) 2.744(4) 142(3) y 2_546 N1C H2C O4A 0.94(3) 1.80(3) 2.714(4) 166(3) y 2_646 N1C H3C O3A 0.90(2) 1.93(3) 2.739(3) 149(3) y 1_555 N2C H4C O4C 0.82(2) 2.23(3) 3.036(3) 165(3) y 2_546 O2C H5C O2B 0.88(3) 1.88(3) 2.745(4) 166(4) y 1_554