# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Dr Carl Gorbitz' _publ_contact_author_email C.H.GORBITZ@KJEMI.UIO.NO loop_ _publ_author_name C.Gorbitz M.Nilsen K.Szeto L.W.Tangen data_LSacn _database_code_depnum_ccdc_archive 'CCDC 266867' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Leucyl-L-serine acetonitrile solvate ; _chemical_name_common 'L-Leucyl-L-serine acetonitrile solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9.17 H18.26 N2.08 O4' _chemical_formula_weight 221.45 _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 65' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 18.1402(3) _cell_length_b 18.1402(3) _cell_length_c 6.1582(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1754.96(7) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 8909 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.24 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.850 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 718 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8882 _exptl_absorpt_correction_T_max 0.9854 _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 11812 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1554 _reflns_number_gt 1482 _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^)+(0.0458P)^2^+0.1150P] 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 1554 _refine_ls_number_parameters 176 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.009 _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 0.08215(6) 0.63612(6) 0.5952(3) 0.0202(2) Uani 1 1 d . . . O2 O 0.28177(6) 0.75171(7) 0.9883(3) 0.0214(2) Uani 1 1 d . . . H5 H 0.3162(15) 0.8060(16) 0.985(4) 0.051(6) Uiso 1 1 d . . . O3 O 0.35195(6) 0.87165(6) 0.3594(3) 0.0216(2) Uani 1 1 d . . . O4 O 0.37961(6) 0.89566(6) 0.7144(3) 0.0208(2) Uani 1 1 d . . . N1 N 0.00376(6) 0.55207(6) 0.2354(3) 0.01439(19) Uani 1 1 d . . . H1 H -0.0326(11) 0.5372(11) 0.119(3) 0.022 Uiso 1 1 d . . . H2 H -0.0262(11) 0.5527(11) 0.346(3) 0.022 Uiso 1 1 d . . . H3 H 0.0218(11) 0.5159(11) 0.255(3) 0.022 Uiso 1 1 d . . . N2 N 0.20574(6) 0.72707(7) 0.4217(3) 0.0169(2) Uani 1 1 d . . . H4 H 0.2325(11) 0.7462(11) 0.297(3) 0.020 Uiso 1 1 d . . . C1 C 0.08226(7) 0.63667(8) 0.2040(3) 0.0148(2) Uani 1 1 d . . . H11 H 0.1222 0.6287 0.1080 0.018 Uiso 1 1 calc R . . C2 C 0.06077(8) 0.69962(8) 0.0932(3) 0.0191(2) Uani 1 1 d . . . H21 H 0.0388 0.6776 -0.0539 0.023 Uiso 1 1 calc R . . H22 H 0.1145 0.7543 0.0748 0.023 Uiso 1 1 calc R . . C3 C -0.00372(10) 0.71830(9) 0.2066(4) 0.0296(3) Uani 1 1 d . . . H31 H -0.0513 0.6637 0.2649 0.035 Uiso 1 1 calc R . . C4 C -0.03997(10) 0.75367(11) 0.0375(5) 0.0399(4) Uani 1 1 d . . . H41 H -0.0808 0.7665 0.1075 0.060 Uiso 1 1 calc R . . H42 H -0.0688 0.7113 -0.0772 0.060 Uiso 1 1 calc R . . H43 H 0.0065 0.8058 -0.0259 0.060 Uiso 1 1 calc R . . C5 C 0.03668(16) 0.78146(15) 0.3957(5) 0.0539(5) Uani 1 1 d . . . H51 H -0.0059 0.7929 0.4604 0.081 Uiso 1 1 calc R . . H52 H 0.0845 0.8347 0.3413 0.081 Uiso 1 1 calc R . . H53 H 0.0572 0.7570 0.5057 0.081 Uiso 1 1 calc R . . C6 C 0.12351(7) 0.66545(7) 0.4277(3) 0.0153(2) Uani 1 1 d . . . C7 C 0.24965(7) 0.77330(7) 0.6165(3) 0.0151(2) Uani 1 1 d . . . H71 H 0.2125 0.7913 0.6927 0.018 Uiso 1 1 calc R . . C8 C 0.26734(8) 0.71822(8) 0.7735(3) 0.0180(2) Uani 1 1 d . . . H81 H 0.2182 0.6595 0.7737 0.022 Uiso 1 1 calc R . . H82 H 0.3179 0.7158 0.7233 0.022 Uiso 1 1 calc R . . C9 C 0.33345(8) 0.85399(7) 0.5549(3) 0.0155(2) Uani 1 1 d . . . N1B N -0.013(2) 1.009(5) 1.0415(14) 0.110(16) Uiso 0.059(4) 1 d PD . 1 C1B C -0.007(3) 1.009(6) 0.8580(12) 0.110(16) Uiso 0.059(4) 1 d PD . 1 C2B C -0.002(6) 1.009(7) 0.6197(14) 0.110(16) Uiso 0.059(4) 1 d PD . 1 N1C N -0.1056(3) 0.938(5) 0.836(10) 0.09(3) Uiso 0.025(6) 1 d PD . 2 C1C C -0.0384(4) 0.966(5) 0.902(10) 0.09(3) Uiso 0.025(6) 1 d PD . 2 C2C C 0.049(4) 1.001(10) 0.98(2) 0.09(3) Uiso 0.025(6) 1 d PD . 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 O1 0.0169(4) 0.0232(4) 0.0139(4) -0.0014(3) 0.0011(3) 0.0050(3) O2 0.0232(4) 0.0220(5) 0.0123(4) -0.0005(3) -0.0012(3) 0.0061(4) O3 0.0227(4) 0.0173(4) 0.0158(4) 0.0010(3) 0.0007(4) 0.0034(4) O4 0.0192(4) 0.0186(4) 0.0172(4) -0.0043(4) -0.0016(4) 0.0038(3) N1 0.0125(4) 0.0162(4) 0.0133(4) -0.0018(4) -0.0017(4) 0.0063(4) N2 0.0153(5) 0.0184(5) 0.0107(5) -0.0007(4) -0.0004(4) 0.0037(4) C1 0.0131(5) 0.0167(5) 0.0121(5) -0.0010(4) -0.0006(4) 0.0057(4) C2 0.0196(5) 0.0202(5) 0.0167(5) 0.0025(5) 0.0006(5) 0.0092(5) C3 0.0314(7) 0.0291(7) 0.0355(8) 0.0095(6) 0.0110(6) 0.0206(6) C4 0.0306(7) 0.0345(8) 0.0595(12) 0.0118(8) 0.0006(8) 0.0199(7) C5 0.0912(15) 0.0668(12) 0.0363(9) -0.0084(9) 0.0009(10) 0.0640(12) C6 0.0150(5) 0.0161(5) 0.0131(5) -0.0021(4) -0.0021(4) 0.0066(4) C7 0.0144(5) 0.0156(5) 0.0120(5) -0.0022(4) -0.0012(4) 0.0050(4) C8 0.0213(6) 0.0160(5) 0.0138(6) -0.0002(4) -0.0010(4) 0.0073(5) C9 0.0161(5) 0.0133(5) 0.0163(5) -0.0013(4) 0.0000(4) 0.0066(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 O1 C6 1.2295(16) . ? O2 C8 1.4241(15) . ? O2 H5 0.86(2) . ? O3 C9 1.2483(17) . ? O4 C9 1.2667(16) . ? N1 C1 1.4950(15) . ? N1 H1 0.92(2) . ? N1 H2 0.87(2) . ? N1 H3 0.876(19) . ? N2 C6 1.3447(16) . ? N2 C7 1.4524(15) . ? N2 H4 0.883(19) . ? C1 C6 1.5293(17) . ? C1 C2 1.5384(17) . ? C1 H11 1.0000 . ? C2 C3 1.5387(19) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 C4 1.533(2) . ? C3 C5 1.538(3) . ? C3 H31 1.0000 . ? C4 H41 0.9800 . ? C4 H42 0.9800 . ? C4 H43 0.9800 . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 0.9800 . ? C7 C8 1.5350(17) . ? C7 C9 1.5401(16) . ? C7 H71 1.0000 . ? C8 H81 0.9900 . ? C8 H82 0.9900 . ? N1B C1B 1.1362(11) . ? C1B C2B 1.4702(10) . ? N1C C1C 1.1362(14) . ? C1C C2C 1.470(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 H5 109.7(18) . . ? C1 N1 H1 112.1(11) . . ? C1 N1 H2 111.5(11) . . ? H1 N1 H2 104.4(14) . . ? C1 N1 H3 105.5(11) . . ? H1 N1 H3 111.8(17) . . ? H2 N1 H3 111.6(18) . . ? C6 N2 C7 121.17(11) . . ? C6 N2 H4 121.0(11) . . ? C7 N2 H4 117.2(11) . . ? N1 C1 C6 106.65(9) . . ? N1 C1 C2 110.76(9) . . ? C6 C1 C2 114.10(10) . . ? N1 C1 H11 108.4 . . ? C6 C1 H11 108.4 . . ? C2 C1 H11 108.4 . . ? C1 C2 C3 117.70(11) . . ? C1 C2 H21 107.9 . . ? C3 C2 H21 107.9 . . ? C1 C2 H22 107.9 . . ? C3 C2 H22 107.9 . . ? H21 C2 H22 107.2 . . ? C4 C3 C5 110.28(14) . . ? C4 C3 C2 108.44(14) . . ? C5 C3 C2 112.10(14) . . ? C4 C3 H31 108.7 . . ? C5 C3 H31 108.7 . . ? C2 C3 H31 108.7 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? C3 C5 H51 109.5 . . ? C3 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C3 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? O1 C6 N2 124.47(12) . . ? O1 C6 C1 121.30(10) . . ? N2 C6 C1 114.15(11) . . ? N2 C7 C8 112.15(10) . . ? N2 C7 C9 109.94(10) . . ? C8 C7 C9 110.21(10) . . ? N2 C7 H71 108.1 . . ? C8 C7 H71 108.1 . . ? C9 C7 H71 108.1 . . ? O2 C8 C7 111.15(10) . . ? O2 C8 H81 109.4 . . ? C7 C8 H81 109.4 . . ? O2 C8 H82 109.4 . . ? C7 C8 H82 109.4 . . ? H81 C8 H82 108.0 . . ? O3 C9 O4 125.61(11) . . ? O3 C9 C7 119.51(11) . . ? O4 C9 C7 114.84(11) . . ? N1B C1B C2B 178(4) . . ? N1C C1C C2C 178(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 N1 C1 C6 N2 161.90(10) . . . . yes C1 C6 N2 C7 167.70(11) . . . . yes C6 N2 C7 C9 -165.20(10) . . . . yes N2 C7 C9 O3 2.53(16) . . . . yes N1 C1 C2 C3 58.21(15) . . . . yes C1 C2 C3 C4 -159.32(12) . . . . yes C1 C2 C3 C5 78.70(16) . . . . yes N2 C7 C8 O2 -159.35(10) . . . . yes C7 C8 O2 H5 -45.7(16) . . . . yes C6 C1 C2 C3 -62.14(15) . . . . ? C7 N2 C6 O1 -9.13(19) . . . . ? N1 C1 C6 O1 -21.16(15) . . . . ? C2 C1 C6 O1 101.46(13) . . . . ? C2 C1 C6 N2 -75.48(13) . . . . ? C6 N2 C7 C8 71.80(15) . . . . ? C9 C7 C8 O2 77.81(13) . . . . ? C8 C7 C9 O3 126.65(12) . . . . ? N2 C7 C9 O4 -175.13(10) . . . . ? C8 C7 C9 O4 -51.00(14) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.230 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.032 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 O4 0.92(2) 1.87(2) 2.7841(14) 175.4(16) y 5_454 N1 H2 O3 0.87(2) 1.978(19) 2.8080(14) 158.0(16) y 5_455 N1 H3 O4 0.876(19) 2.012(19) 2.8134(14) 151.6(17) y 2_664 N2 H4 O2 0.883(19) 2.08(2) 2.9342(14) 162.4(16) y 1_554 O2 H5 O4 0.86(2) 2.21(3) 2.8598(13) 132(2) y 1_555 C2 H21 O1 0.99 2.54 3.3656(16) 141.0 y 1_554 data_LS _database_code_depnum_ccdc_archive 'CCDC 266868' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Leucyl-L-serine ; _chemical_name_common L-Leucyl-L-serine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H18 N2 O4' _chemical_formula_weight 218.25 _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 65' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 18.1253(3) _cell_length_b 18.1253(3) _cell_length_c 6.1497(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1749.66(7) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 9371 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.27 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.850 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9090 _exptl_absorpt_correction_T_max 0.9856 _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 12017 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1581 _reflns_number_gt 1542 _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^)+(0.0449P)^2^+0.1732P] 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 1581 _refine_ls_number_parameters 153 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.36397(6) 0.91757(6) 0.25890(16) 0.0201(2) Uani 1 1 d . . . O2 O 0.24832(6) 0.71818(6) -0.13405(15) 0.0215(2) Uani 1 1 d . . . H5 H 0.1985(13) 0.6807(13) -0.128(4) 0.032 Uiso 1 1 d . . . O3 O 0.12829(6) 0.64813(6) 0.49464(16) 0.0215(2) Uani 1 1 d . . . O4 O 0.10422(5) 0.62041(6) 0.13962(17) 0.0207(2) Uani 1 1 d . . . N1 N 0.44805(6) 0.99613(6) 0.61865(19) 0.01433(19) Uani 1 1 d . . . H1 H 0.4845(11) 0.9781(11) 0.601(3) 0.022 Uiso 1 1 d . . . H2 H 0.4470(11) 1.0253(11) 0.509(4) 0.022 Uiso 1 1 d . . . H3 H 0.4620(11) 1.0311(12) 0.734(4) 0.022 Uiso 1 1 d . . . N2 N 0.27295(6) 0.79415(6) 0.43252(18) 0.0168(2) Uani 1 1 d . . . H4 H 0.2584(11) 0.7687(11) 0.555(3) 0.020 Uiso 1 1 d . . . C1 C 0.36344(7) 0.91764(7) 0.6500(2) 0.0146(2) Uani 1 1 d . . . H11 H 0.3714 0.8777 0.7461 0.018 Uiso 1 1 calc R . . C2 C 0.30053(7) 0.93915(8) 0.7610(2) 0.0188(2) Uani 1 1 d . . . H21 H 0.2457 0.8854 0.7793 0.023 Uiso 1 1 calc R . . H22 H 0.3225 0.9611 0.9084 0.023 Uiso 1 1 calc R . . C3 C 0.28201(9) 1.00363(9) 0.6479(3) 0.0298(3) Uani 1 1 d . . . H3A H 0.3367 1.0513 0.5900 0.036 Uiso 1 1 calc R . . C4 C 0.24656(11) 1.03973(10) 0.8171(4) 0.0399(4) Uani 1 1 d . . . H41 H 0.2361 1.0824 0.7485 0.060 Uiso 1 1 calc R . . H42 H 0.2879 1.0663 0.9353 0.060 Uiso 1 1 calc R . . H43 H 0.1931 0.9935 0.8759 0.060 Uiso 1 1 calc R . . C5 C 0.21911(15) 0.96362(17) 0.4584(4) 0.0557(6) Uani 1 1 d . . . H51 H 0.2069 1.0061 0.3958 0.083 Uiso 1 1 calc R . . H52 H 0.1661 0.9150 0.5117 0.083 Uiso 1 1 calc R . . H53 H 0.2442 0.9443 0.3467 0.083 Uiso 1 1 calc R . . C6 C 0.33458(7) 0.87632(7) 0.4265(2) 0.0152(2) Uani 1 1 d . . . C8 C 0.28185(7) 0.73253(8) 0.0808(2) 0.0177(2) Uani 1 1 d . . . H81 H 0.3406 0.7817 0.0806 0.021 Uiso 1 1 calc R . . H82 H 0.2842 0.6818 0.1310 0.021 Uiso 1 1 calc R . . C7 C 0.22677(7) 0.75028(7) 0.2378(2) 0.0150(2) Uani 1 1 d . . . H7A H 0.2089 0.7875 0.1615 0.018 Uiso 1 1 calc R . . C9 C 0.14587(7) 0.66650(7) 0.2994(2) 0.0153(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0229(4) 0.0164(4) 0.0136(4) 0.0015(3) -0.0011(4) 0.0043(3) O2 0.0216(4) 0.0226(4) 0.0127(5) -0.0013(3) -0.0006(4) 0.0055(4) O3 0.0165(4) 0.0220(4) 0.0164(5) 0.0007(4) 0.0008(3) 0.0025(3) O4 0.0182(4) 0.0185(4) 0.0172(5) -0.0018(4) -0.0045(4) 0.0032(3) N1 0.0165(4) 0.0119(4) 0.0134(5) -0.0016(4) -0.0017(4) 0.0061(3) N2 0.0184(4) 0.0150(4) 0.0105(5) -0.0003(4) -0.0008(4) 0.0034(4) C1 0.0163(5) 0.0126(5) 0.0121(6) -0.0008(4) -0.0010(4) 0.0052(4) C2 0.0195(5) 0.0187(5) 0.0168(6) 0.0005(5) 0.0026(5) 0.0085(4) C3 0.0295(6) 0.0318(7) 0.0355(8) 0.0109(7) 0.0101(6) 0.0209(6) C4 0.0347(7) 0.0311(7) 0.0597(12) 0.0005(8) 0.0121(8) 0.0208(6) C5 0.0703(13) 0.0948(16) 0.0369(10) 0.0000(11) -0.0089(10) 0.0676(13) C6 0.0164(5) 0.0150(5) 0.0132(5) -0.0016(4) -0.0021(4) 0.0070(4) C8 0.0161(5) 0.0206(5) 0.0138(6) -0.0012(4) -0.0003(4) 0.0074(4) C7 0.0156(5) 0.0145(5) 0.0119(5) -0.0011(4) -0.0023(4) 0.0053(4) C9 0.0130(5) 0.0148(5) 0.0169(6) -0.0003(4) -0.0014(4) 0.0061(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 O1 C6 1.2276(17) . ? O2 C8 1.4228(15) . ? O2 H5 0.81(2) . ? O3 C9 1.2439(17) . ? O4 C9 1.2661(16) . ? N1 C1 1.4937(14) . ? N1 H1 0.878(19) . ? N1 H2 0.86(2) . ? N1 H3 0.90(2) . ? N2 C6 1.3431(15) . ? N2 C7 1.4494(15) . ? N2 H4 0.85(2) . ? C1 C6 1.5267(18) . ? C1 C2 1.5372(16) . ? C1 H11 1.0000 . ? C2 C3 1.5344(19) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 C4 1.531(2) . ? C3 C5 1.535(3) . ? C3 H3A 1.0000 . ? C4 H41 0.9800 . ? C4 H42 0.9800 . ? C4 H43 0.9800 . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 0.9800 . ? C8 C7 1.5344(17) . ? C8 H81 0.9900 . ? C8 H82 0.9900 . ? C7 C9 1.5404(16) . ? C7 H7A 1.0000 . ? 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 C8 O2 H5 107.8(16) . . ? C1 N1 H1 105.5(11) . . ? C1 N1 H2 110.9(11) . . ? H1 N1 H2 112.5(19) . . ? C1 N1 H3 111.2(12) . . ? H1 N1 H3 111.1(17) . . ? H2 N1 H3 105.7(15) . . ? C6 N2 C7 121.17(11) . . ? C6 N2 H4 119.0(12) . . ? C7 N2 H4 119.6(12) . . ? N1 C1 C6 106.74(9) . . ? N1 C1 C2 110.75(9) . . ? C6 C1 C2 114.10(10) . . ? N1 C1 H11 108.4 . . ? C6 C1 H11 108.4 . . ? C2 C1 H11 108.4 . . ? C3 C2 C1 117.68(11) . . ? C3 C2 H21 107.9 . . ? C1 C2 H21 107.9 . . ? C3 C2 H22 107.9 . . ? C1 C2 H22 107.9 . . ? H21 C2 H22 107.2 . . ? C4 C3 C5 110.29(14) . . ? C4 C3 C2 108.41(14) . . ? C5 C3 C2 112.19(14) . . ? C4 C3 H3A 108.6 . . ? C5 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? C3 C5 H51 109.5 . . ? C3 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C3 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? O1 C6 N2 124.44(12) . . ? O1 C6 C1 121.27(9) . . ? N2 C6 C1 114.22(11) . . ? O2 C8 C7 111.07(10) . . ? O2 C8 H81 109.4 . . ? C7 C8 H81 109.4 . . ? O2 C8 H82 109.4 . . ? C7 C8 H82 109.4 . . ? H81 C8 H82 108.0 . . ? N2 C7 C8 112.16(10) . . ? N2 C7 C9 109.97(10) . . ? C8 C7 C9 110.27(9) . . ? N2 C7 H7A 108.1 . . ? C8 C7 H7A 108.1 . . ? C9 C7 H7A 108.1 . . ? O3 C9 O4 125.73(11) . . ? O3 C9 C7 119.44(11) . . ? O4 C9 C7 114.78(11) . . ? 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 C6 N2 161.91(10) . . . . yes C1 C6 N2 C7 167.73(10) . . . . yes C6 N2 C7 C9 -165.10(10) . . . . yes N2 C7 C9 O3 2.44(16) . . . . yes N1 C1 C2 C3 58.15(15) . . . . yes C1 C2 C3 C4 -159.40(12) . . . . yes C1 C2 C3 C5 78.56(16) . . . . yes N2 C7 C8 O2 -159.30(10) . . . . yes C7 C8 O2 H5 -53.6(15) . . . . yes C6 C1 C2 C3 -62.30(14) . . . . ? C7 N2 C6 O1 -9.24(19) . . . . ? C7 N2 C6 C1 167.73(10) . . . . ? N1 C1 C6 O1 -21.02(14) . . . . ? C2 C1 C6 O1 101.65(13) . . . . ? N1 C1 C6 N2 161.91(10) . . . . ? C2 C1 C6 N2 -75.42(12) . . . . ? C6 N2 C7 C8 71.79(14) . . . . ? O2 C8 C7 C9 77.77(12) . . . . ? C8 C7 C9 O3 126.64(12) . . . . ? N2 C7 C9 O4 -175.17(10) . . . . ? C8 C7 C9 O4 -50.97(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.033 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 O4 0.879(19) 2.009(19) 2.8076(14) 150.8(16) y 3_565 N1 H2 O3 0.86(2) 1.99(2) 2.8069(14) 157.2(16) y 6_664 N1 H3 O4 0.90(2) 1.88(2) 2.7814(14) 175.9(16) y 6_665 N2 H4 O2 0.85(2) 2.09(2) 2.9300(14) 168.8(17) y 1_556 O2 H5 O4 0.81(3) 2.23(3) 2.8576(13) 134(2) y 1_555 C2 H22 O1 0.99 2.53 3.3618(17) 141.0 y 1_556 data_LSI2 _database_code_depnum_ccdc_archive 'CCDC 266869' _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-Leucyl-L-serine iodine complex ; _chemical_name_common 'L-Leucyl-L-serine iodine complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H18 I0.07 N2 O4' _chemical_formula_weight 226.88 _chemical_absolute_configuration 'from Flack parameter' 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' I I -0.4742 1.8119 '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 65' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 18.1470(3) _cell_length_b 18.1470(3) _cell_length_c 6.1536(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1754.97(7) _cell_formula_units_Z 6 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 5379 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 37.99 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.850 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_crystal_density_meas 1.299 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method pycnometer _exptl_crystal_F_000 730 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7623 _exptl_absorpt_correction_T_max 0.9586 _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 27813 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 38.19 _reflns_number_total 6207 _reflns_number_gt 5152 _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 two sets of exposures with the detector set at 2\q = 29\% and three sets of exposures with the detector set at 2\q = 55\%, 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^)+(0.0699P)^2^+1.4400P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(16) _refine_ls_number_reflns 6207 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1727 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.44654(9) 0.36430(8) 0.1827(2) 0.0198(2) Uani 1 1 d . . . O2 O 0.53011(10) 0.24817(9) -0.2098(2) 0.0216(2) Uani 1 1 d . . . H5 H 0.511(2) 0.185(2) -0.203(6) 0.038(9) Uiso 1 1 d . . . O3 O 0.48035(9) 0.12847(8) 0.4193(2) 0.0211(2) Uani 1 1 d . . . O4 O 0.48403(9) 0.10431(8) 0.0641(2) 0.0207(2) Uani 1 1 d . . . N1 N 0.45157(9) 0.44800(8) 0.5433(2) 0.0142(2) Uani 1 1 d . . . H1 H 0.5107(19) 0.4865(18) 0.528(5) 0.021 Uiso 1 1 d . . . H2 H 0.4283(19) 0.4479(18) 0.436(5) 0.021 Uiso 1 1 d . . . H3 H 0.4374(19) 0.4547(18) 0.657(5) 0.021 Uiso 1 1 d . . . N2 N 0.47856(9) 0.27284(9) 0.3570(2) 0.0165(2) Uani 1 1 d . . . H4 H 0.4801(18) 0.2559(19) 0.480(5) 0.020 Uiso 1 1 d . . . C1 C 0.44574(10) 0.36371(10) 0.5744(2) 0.0147(2) Uani 1 1 d . . . H11 H 0.4936 0.3718 0.6707 0.018 Uiso 1 1 calc R . . C2 C 0.36137(11) 0.30066(11) 0.6852(3) 0.0185(3) Uani 1 1 d . . . H21 H 0.3605 0.2460 0.7035 0.022 Uiso 1 1 calc R . . H22 H 0.3614 0.3226 0.8325 0.022 Uiso 1 1 calc R . . C3 C 0.27829(12) 0.28191(14) 0.5720(4) 0.0297(4) Uani 1 1 d . . . H31 H 0.2852 0.3364 0.5130 0.036 Uiso 1 1 calc R . . C4 C 0.20669(15) 0.24655(17) 0.7411(5) 0.0392(6) Uani 1 1 d . . . H41 H 0.1531 0.2339 0.6710 0.059 Uiso 1 1 calc R . . H42 H 0.2203 0.2888 0.8561 0.059 Uiso 1 1 calc R . . H43 H 0.2008 0.1943 0.8043 0.059 Uiso 1 1 calc R . . C5 C 0.25530(18) 0.2178(2) 0.3823(5) 0.0524(8) Uani 1 1 d . . . H51 H 0.2997 0.2425 0.2707 0.079 Uiso 1 1 calc R . . H52 H 0.2006 0.2053 0.3193 0.079 Uiso 1 1 calc R . . H53 H 0.2511 0.1651 0.4371 0.079 Uiso 1 1 calc R . . C6 C 0.45831(10) 0.33467(10) 0.3513(3) 0.0153(2) Uani 1 1 d . . . C7 C 0.47640(10) 0.22669(9) 0.1624(2) 0.0144(2) Uani 1 1 d . . . H71 H 0.4213 0.2087 0.0861 0.017 Uiso 1 1 calc R . . C8 C 0.54916(11) 0.28188(10) 0.0050(3) 0.0176(3) Uani 1 1 d . . . H81 H 0.5585 0.3405 0.0045 0.021 Uiso 1 1 calc R . . H82 H 0.6022 0.2845 0.0554 0.021 Uiso 1 1 calc R . . C9 C 0.47935(10) 0.14597(9) 0.2240(3) 0.0146(2) Uani 1 1 d . . . I1 I 0.0189(7) 0.0121(14) 0.216(15) 0.056(3) Uiso 0.038(3) 1 d P . . I2 I 0.0141(13) 0.0178(9) 0.133(16) 0.048(4) Uiso 0.030(3) 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 0.0311(6) 0.0229(5) 0.0125(4) -0.0005(4) -0.0026(4) 0.0187(5) O2 0.0335(7) 0.0237(6) 0.0114(4) -0.0008(4) 0.0003(4) 0.0172(5) O3 0.0328(7) 0.0162(5) 0.0161(5) 0.0013(4) 0.0002(4) 0.0137(5) O4 0.0312(6) 0.0188(5) 0.0163(5) -0.0052(4) -0.0029(4) 0.0156(5) N1 0.0170(5) 0.0165(5) 0.0125(5) -0.0016(4) -0.0003(4) 0.0109(4) N2 0.0260(6) 0.0182(5) 0.0107(5) -0.0012(4) -0.0006(4) 0.0152(5) C1 0.0187(6) 0.0166(6) 0.0117(5) -0.0010(4) -0.0006(4) 0.0111(5) C2 0.0199(6) 0.0191(6) 0.0174(6) 0.0021(5) 0.0019(5) 0.0105(5) C3 0.0193(7) 0.0308(9) 0.0347(10) 0.0101(8) -0.0004(7) 0.0094(7) C4 0.0238(9) 0.0343(11) 0.0592(16) 0.0133(11) 0.0126(10) 0.0143(8) C5 0.0277(11) 0.0620(18) 0.0402(14) -0.0076(13) -0.0083(10) 0.0021(11) C6 0.0196(6) 0.0166(5) 0.0127(5) -0.0011(4) -0.0009(4) 0.0114(5) C7 0.0193(6) 0.0146(5) 0.0118(5) -0.0012(4) -0.0006(4) 0.0103(5) C8 0.0223(6) 0.0157(6) 0.0130(6) 0.0001(4) 0.0007(5) 0.0082(5) C9 0.0172(5) 0.0125(5) 0.0148(6) -0.0015(4) -0.0007(4) 0.0080(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 O1 C6 1.235(2) . ? O2 C8 1.425(2) . ? O2 H5 1.03(4) . ? O3 C9 1.245(2) . ? O4 C9 1.2694(19) . ? N1 C1 1.492(2) . ? N1 H1 0.95(3) . ? N1 H2 0.78(3) . ? N1 H3 0.78(3) . ? N2 C6 1.344(2) . ? N2 C7 1.4505(19) . ? N2 H4 0.82(3) . ? C1 C6 1.528(2) . ? C1 C2 1.539(2) . ? C1 H11 1.0000 . ? C2 C3 1.537(3) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 C4 1.533(3) . ? C3 C5 1.551(4) . ? C3 H31 1.0000 . ? C4 H41 0.9800 . ? C4 H42 0.9800 . ? C4 H43 0.9800 . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 0.9800 . ? C7 C8 1.537(2) . ? C7 C9 1.540(2) . ? C7 H71 1.0000 . ? C8 H81 0.9900 . ? C8 H82 0.9900 . ? I1 I2 0.535(9) 5 ? I1 I2 0.537(9) . ? 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 C8 O2 H5 108.4(19) . . ? C1 N1 H1 103.9(18) . . ? C1 N1 H2 110(2) . . ? H1 N1 H2 109(3) . . ? C1 N1 H3 101(2) . . ? H1 N1 H3 108(3) . . ? H2 N1 H3 123(3) . . ? C6 N2 C7 121.37(13) . . ? C6 N2 H4 114(2) . . ? C7 N2 H4 123(2) . . ? N1 C1 C6 106.99(12) . . ? N1 C1 C2 110.69(12) . . ? C6 C1 C2 113.98(13) . . ? N1 C1 H11 108.3 . . ? C6 C1 H11 108.3 . . ? C2 C1 H11 108.3 . . ? C3 C2 C1 117.71(14) . . ? C3 C2 H21 107.9 . . ? C1 C2 H21 107.9 . . ? C3 C2 H22 107.9 . . ? C1 C2 H22 107.9 . . ? H21 C2 H22 107.2 . . ? C4 C3 C2 108.51(19) . . ? C4 C3 C5 110.1(2) . . ? C2 C3 C5 111.9(2) . . ? C4 C3 H31 108.8 . . ? C2 C3 H31 108.8 . . ? C5 C3 H31 108.8 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? C3 C5 H51 109.5 . . ? C3 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C3 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? O1 C6 N2 124.36(14) . . ? O1 C6 C1 121.08(13) . . ? N2 C6 C1 114.49(13) . . ? N2 C7 C8 112.17(13) . . ? N2 C7 C9 110.01(12) . . ? C8 C7 C9 110.36(12) . . ? N2 C7 H71 108.1 . . ? C8 C7 H71 108.1 . . ? C9 C7 H71 108.1 . . ? O2 C8 C7 111.09(13) . . ? O2 C8 H81 109.4 . . ? C7 C8 H81 109.4 . . ? O2 C8 H82 109.4 . . ? C7 C8 H82 109.4 . . ? H81 C8 H82 108.0 . . ? O3 C9 O4 125.60(14) . . ? O3 C9 C7 119.49(13) . . ? O4 C9 C7 114.85(14) . . ? 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 C3 58.2(2) . . . . ? C6 C1 C2 C3 -62.5(2) . . . . ? C1 C2 C3 C4 -159.22(17) . . . . ? C1 C2 C3 C5 79.1(2) . . . . ? C7 N2 C6 O1 -9.0(3) . . . . ? C7 N2 C6 C1 167.80(14) . . . . ? N1 C1 C6 O1 -20.8(2) . . . . ? C2 C1 C6 O1 101.94(18) . . . . ? N1 C1 C6 N2 162.29(13) . . . . ? C2 C1 C6 N2 -75.00(17) . . . . ? C6 N2 C7 C8 71.38(19) . . . . ? C6 N2 C7 C9 -165.37(14) . . . . ? N2 C7 C8 O2 -159.40(13) . . . . ? C9 C7 C8 O2 77.55(16) . . . . ? N2 C7 C9 O3 2.2(2) . . . . ? C8 C7 C9 O3 126.51(16) . . . . ? N2 C7 C9 O4 -175.08(14) . . . . ? C8 C7 C9 O4 -50.77(18) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.511 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.089 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 O4 0.95(3) 1.96(3) 2.8148(19) 150(3) y 3_665 N1 H2 O3 0.78(3) 2.09(3) 2.8068(19) 153(3) y 6_554 N1 H3 O4 0.78(3) 2.03(3) 2.7803(19) 162(3) y 6_555 N2 H4 O2 0.82(3) 2.15(3) 2.9325(19) 159(3) y 1_556 O2 H5 O4 1.03(4) 2.08(4) 2.8592(19) 130(3) y 1_555 C2 H22 O1 0.99 2.54 3.363(2) 141 y 1_556