# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Debasish Haldar' _publ_contact_author_email 'deba h76@yahoo.com' loop_ _publ_author_name S.Maity S.Maity P.Jana 'Debasish Haldar' data_as _database_code_depnum_ccdc_archive 'CCDC 848503' #TrackingRef 'web_deposit_cif_file_0_DebasishHaldar_1324548500.gly-aib-gly.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H25 N3 O6' _chemical_formula_sum 'C14 H25 N3 O6' _chemical_formula_weight 331.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.630(11) _cell_length_b 5.8524(19) _cell_length_c 22.101(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.912(6) _cell_angle_gamma 90.00 _cell_volume 3501(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2076 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 27.84 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13791 _diffrn_reflns_av_R_equivalents 0.1093 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3764 _reflns_number_gt 2233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+1.7672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3764 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.20932(7) 0.2208(4) 0.86167(10) 0.0199(5) Uani 1 1 d . . . O2 O 0.01491(7) 0.9571(4) 0.82987(11) 0.0246(6) Uani 1 1 d . . . O3 O -0.02183(8) 0.6343(4) 0.83634(14) 0.0335(6) Uani 1 1 d . . . O4 O 0.18320(7) 0.3645(4) 1.01054(10) 0.0183(5) Uani 1 1 d . . . O5 O 0.13846(7) 0.0982(4) 0.86284(10) 0.0190(5) Uani 1 1 d . . . O6 O 0.07777(7) 0.6863(4) 0.98533(11) 0.0205(5) Uani 1 1 d . . . N1 N 0.21482(8) 0.0238(4) 0.95030(12) 0.0156(6) Uani 1 1 d . . . H1 H 0.2455 0.0034 0.9619 0.019 Uiso 1 1 calc R . . N2 N 0.12583(8) 0.1186(4) 1.00954(12) 0.0151(5) Uani 1 1 d . . . H2 H 0.1157 -0.0206 1.0039 0.018 Uiso 1 1 calc R . . N3 N 0.07526(8) 0.4390(4) 0.90626(12) 0.0165(6) Uani 1 1 d . . . H3 H 0.0770 0.3002 0.8949 0.020 Uiso 1 1 calc R . . C1 C 0.22701(12) 0.4341(6) 0.78679(17) 0.0250(8) Uani 1 1 d . . . H1A H 0.2384 0.5601 0.8182 0.037 Uiso 1 1 calc R . . H1B H 0.2157 0.4895 0.7410 0.037 Uiso 1 1 calc R . . H1C H 0.2536 0.3279 0.7980 0.037 Uiso 1 1 calc R . . C2 C 0.18459(10) 0.3146(5) 0.79184(15) 0.0173(7) Uani 1 1 d . . . C3 C 0.18335(10) 0.1132(5) 0.88862(15) 0.0149(6) Uani 1 1 d . . . C4 C 0.19491(10) -0.0366(5) 0.99638(15) 0.0155(6) Uani 1 1 d . . . H4A H 0.2216 -0.0830 1.0403 0.019 Uiso 1 1 calc R . . H4B H 0.1723 -0.1644 0.9776 0.019 Uiso 1 1 calc R . . C5 C 0.16770(10) 0.1668(5) 1.00631(14) 0.0140(6) Uani 1 1 d . . . C6 C 0.09684(10) 0.2946(5) 1.02229(15) 0.0151(6) Uani 1 1 d . . . C7 C 0.08389(9) 0.4905(5) 0.97039(14) 0.0138(6) Uani 1 1 d . . . C8 C 0.06293(11) 0.6228(6) 0.85689(16) 0.0190(7) Uani 1 1 d . . . H8A H 0.0613 0.5631 0.8150 0.023 Uiso 1 1 calc R . . H8B H 0.0888 0.7376 0.8749 0.023 Uiso 1 1 calc R . . C9 C 0.01399(11) 0.7329(6) 0.84104(15) 0.0183(7) Uani 1 1 d . . . C10 C -0.03189(12) 1.0740(6) 0.80758(19) 0.0319(9) Uani 1 1 d . . . H10A H -0.0542 1.0304 0.7614 0.048 Uiso 1 1 calc R . . H10B H -0.0266 1.2362 0.8096 0.048 Uiso 1 1 calc R . . H10C H -0.0458 1.0329 0.8370 0.048 Uiso 1 1 calc R . . C11 C 0.12570(12) 0.3883(6) 1.09506(16) 0.0240(7) Uani 1 1 d . . . H11A H 0.1337 0.2654 1.1273 0.036 Uiso 1 1 calc R . . H11B H 0.1059 0.4994 1.1031 0.036 Uiso 1 1 calc R . . H11C H 0.1556 0.4589 1.1005 0.036 Uiso 1 1 calc R . . C12 C 0.04824(11) 0.1867(6) 1.01196(17) 0.0208(7) Uani 1 1 d . . . H12A H 0.0310 0.1247 0.9666 0.031 Uiso 1 1 calc R . . H12B H 0.0281 0.3011 1.0180 0.031 Uiso 1 1 calc R . . H12C H 0.0552 0.0668 1.0449 0.031 Uiso 1 1 calc R . . C13 C 0.14462(11) 0.4866(6) 0.78302(17) 0.0248(8) Uani 1 1 d . . . H13A H 0.1169 0.4074 0.7823 0.037 Uiso 1 1 calc R . . H13B H 0.1342 0.5680 0.7408 0.037 Uiso 1 1 calc R . . H13C H 0.1576 0.5928 0.8205 0.037 Uiso 1 1 calc R . . C14 C 0.16443(11) 0.1184(6) 0.74067(16) 0.0236(7) Uani 1 1 d . . . H14A H 0.1907 0.0142 0.7483 0.035 Uiso 1 1 calc R . . H14B H 0.1507 0.1779 0.6949 0.035 Uiso 1 1 calc R . . H14C H 0.1392 0.0396 0.7466 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0152(10) 0.0252(14) 0.0190(11) 0.0079(9) 0.0076(9) -0.0016(9) O2 0.0186(11) 0.0183(14) 0.0331(13) 0.0071(10) 0.0090(10) 0.0061(9) O3 0.0161(11) 0.0202(15) 0.0574(17) 0.0006(12) 0.0116(11) -0.0005(9) O4 0.0132(10) 0.0165(13) 0.0238(11) 0.0015(9) 0.0074(8) -0.0023(8) O5 0.0142(10) 0.0234(14) 0.0189(11) 0.0028(9) 0.0075(8) -0.0022(8) O6 0.0253(11) 0.0095(13) 0.0305(12) -0.0028(9) 0.0163(10) -0.0013(9) N1 0.0103(11) 0.0171(15) 0.0203(13) 0.0035(11) 0.0079(10) 0.0028(10) N2 0.0151(12) 0.0095(14) 0.0211(13) -0.0015(10) 0.0089(10) -0.0013(10) N3 0.0183(12) 0.0104(15) 0.0171(13) 0.0007(10) 0.0051(10) 0.0038(10) C1 0.0254(17) 0.026(2) 0.0288(18) 0.0050(15) 0.0173(14) -0.0006(14) C2 0.0189(14) 0.0164(18) 0.0179(15) 0.0034(13) 0.0097(12) 0.0018(12) C3 0.0135(14) 0.0123(17) 0.0203(15) -0.0015(12) 0.0089(12) -0.0027(11) C4 0.0126(13) 0.0148(17) 0.0188(15) 0.0045(12) 0.0072(11) -0.0003(11) C5 0.0112(13) 0.0141(18) 0.0127(14) 0.0032(12) 0.0023(11) -0.0013(11) C6 0.0152(14) 0.0113(17) 0.0207(15) -0.0011(12) 0.0099(12) -0.0005(11) C7 0.0106(13) 0.0115(17) 0.0183(15) -0.0001(12) 0.0058(11) -0.0014(11) C8 0.0181(15) 0.0174(18) 0.0211(16) 0.0053(13) 0.0088(12) 0.0049(12) C9 0.0166(15) 0.0187(19) 0.0152(15) -0.0021(13) 0.0038(12) -0.0005(12) C10 0.0213(17) 0.025(2) 0.039(2) 0.0031(16) 0.0053(15) 0.0104(14) C11 0.0287(17) 0.022(2) 0.0201(16) -0.0017(14) 0.0106(13) -0.0003(14) C12 0.0223(15) 0.0155(19) 0.0315(17) 0.0003(14) 0.0183(14) 0.0002(13) C13 0.0256(17) 0.022(2) 0.0292(18) 0.0053(15) 0.0150(14) 0.0058(14) C14 0.0239(16) 0.025(2) 0.0235(17) -0.0013(14) 0.0128(13) 0.0030(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 O1 C3 1.352(4) . ? O1 C2 1.470(4) . ? O2 C9 1.338(4) . ? O2 C10 1.451(4) . ? O3 C9 1.200(4) . ? O4 C5 1.237(4) . ? O5 C3 1.220(3) . ? O6 C7 1.231(4) . ? N1 C3 1.353(4) . ? N1 C4 1.455(4) . ? N1 H1 0.8600 . ? N2 C5 1.347(4) . ? N2 C6 1.471(4) . ? N2 H2 0.8600 . ? N3 C7 1.348(4) . ? N3 C8 1.451(4) . ? N3 H3 0.8600 . ? C1 C2 1.525(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C14 1.525(5) . ? C2 C13 1.525(4) . ? C4 C5 1.527(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 C11 1.529(4) . ? C6 C12 1.533(4) . ? C6 C7 1.537(4) . ? C8 C9 1.514(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C3 O1 C2 121.1(2) . . ? C9 O2 C10 115.0(3) . . ? C3 N1 C4 117.7(2) . . ? C3 N1 H1 121.2 . . ? C4 N1 H1 121.2 . . ? C5 N2 C6 122.6(3) . . ? C5 N2 H2 118.7 . . ? C6 N2 H2 118.7 . . ? C7 N3 C8 118.6(3) . . ? C7 N3 H3 120.7 . . ? C8 N3 H3 120.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 102.1(2) . . ? O1 C2 C14 109.1(3) . . ? C1 C2 C14 110.7(3) . . ? O1 C2 C13 111.6(2) . . ? C1 C2 C13 110.4(3) . . ? C14 C2 C13 112.3(3) . . ? O5 C3 O1 126.5(3) . . ? O5 C3 N1 123.9(3) . . ? O1 C3 N1 109.6(2) . . ? N1 C4 C5 110.3(2) . . ? N1 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N1 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O4 C5 N2 122.2(3) . . ? O4 C5 C4 121.6(2) . . ? N2 C5 C4 116.2(3) . . ? N2 C6 C11 110.4(2) . . ? N2 C6 C12 108.3(3) . . ? C11 C6 C12 110.3(2) . . ? N2 C6 C7 110.3(2) . . ? C11 C6 C7 109.7(3) . . ? C12 C6 C7 107.6(2) . . ? O6 C7 N3 120.7(3) . . ? O6 C7 C6 120.8(3) . . ? N3 C7 C6 118.2(3) . . ? N3 C8 C9 111.7(2) . . ? N3 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N3 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? O3 C9 O2 123.6(3) . . ? O3 C9 C8 125.5(3) . . ? O2 C9 C8 110.8(3) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C14 H14A 109.5 . . ? C2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.445 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.079 # Attachment 'web_deposit_cif_file_1_DebasishHaldar_1324548500.maba-aib.cif' data_sm _database_code_depnum_ccdc_archive 'CCDC 848504' #TrackingRef 'web_deposit_cif_file_1_DebasishHaldar_1324548500.maba-aib.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H24 N2 O5' _chemical_formula_sum 'C17 H24 N2 O5' _chemical_formula_weight 336.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.2705(9) _cell_length_b 13.3006(8) _cell_length_c 21.2009(17) _cell_angle_alpha 90.00 _cell_angle_beta 108.655(3) _cell_angle_gamma 90.00 _cell_volume 3812.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6483 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 26.78 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14537 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4118 _reflns_number_gt 2854 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1062P)^2^+3.4516P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4118 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 0.98226(11) 0.13620(12) 0.37084(9) 0.0596(5) Uani 1 1 d . . . O5 O 0.89070(15) 0.68238(15) 0.02531(9) 0.0753(6) Uani 1 1 d . . . O2 O 1.01307(11) 0.28990(11) 0.33769(8) 0.0550(4) Uani 1 1 d . . . O3 O 0.78193(11) 0.60299(10) 0.14396(8) 0.0461(4) Uani 1 1 d . . . O4 O 0.82136(15) 0.53140(18) 0.01181(9) 0.0777(6) Uani 1 1 d . . . N1 N 0.85748(12) 0.22602(12) 0.31063(8) 0.0400(4) Uani 1 1 d . . . H1 H 0.8249 0.1748 0.3171 0.048 Uiso 1 1 calc R . . N2 N 0.90682(12) 0.49782(12) 0.14771(8) 0.0381(4) Uani 1 1 d . . . H2 H 0.9339 0.4404 0.1607 0.046 Uiso 1 1 calc R . . C3 C 1.1505(3) 0.1173(4) 0.3665(3) 0.1314(18) Uani 1 1 d . . . H1A H 1.1644 0.1865 0.3601 0.197 Uiso 1 1 calc R . . H1B H 1.1175 0.0869 0.3241 0.197 Uiso 1 1 calc R . . H1C H 1.2113 0.0823 0.3877 0.197 Uiso 1 1 calc R . . C4 C 1.08627(18) 0.1115(2) 0.40872(15) 0.0718(8) Uani 1 1 d . . . C5 C 0.95665(14) 0.22372(14) 0.33946(10) 0.0390(4) Uani 1 1 d . . . C6 C 0.80244(13) 0.30384(13) 0.27114(9) 0.0345(4) Uani 1 1 d . . . C11 C 0.84209(14) 0.37193(13) 0.23695(9) 0.0331(4) Uani 1 1 d . . . H5 H 0.9088 0.3683 0.2408 0.040 Uiso 1 1 calc R . . C10 C 0.78301(14) 0.44534(13) 0.19708(9) 0.0353(4) Uani 1 1 d . . . C12 C 0.82341(14) 0.52129(13) 0.16060(9) 0.0339(4) Uani 1 1 d . . . C13 C 0.95383(14) 0.56560(15) 0.11244(9) 0.0385(4) Uani 1 1 d . . . C16 C 0.87847(16) 0.59037(18) 0.04494(11) 0.0465(5) Uani 1 1 d . . . C17 C 0.8294(3) 0.7085(3) -0.04167(17) 0.1226(18) Uani 1 1 d . . . H10A H 0.8537 0.6749 -0.0734 0.184 Uiso 1 1 calc R . . H10B H 0.8314 0.7799 -0.0477 0.184 Uiso 1 1 calc R . . H10C H 0.7624 0.6880 -0.0482 0.184 Uiso 1 1 calc R . . C2 C 1.1195(3) 0.1798(4) 0.4674(2) 0.1349(18) Uani 1 1 d . . . H11A H 1.1830 0.1583 0.4963 0.202 Uiso 1 1 calc R . . H11B H 1.0725 0.1781 0.4912 0.202 Uiso 1 1 calc R . . H11C H 1.1246 0.2472 0.4526 0.202 Uiso 1 1 calc R . . C14 C 0.9964(2) 0.6568(2) 0.15473(13) 0.0667(7) Uani 1 1 d . . . H12A H 0.9437 0.6953 0.1617 0.100 Uiso 1 1 calc R . . H12B H 1.0315 0.6975 0.1324 0.100 Uiso 1 1 calc R . . H12C H 1.0409 0.6352 0.1969 0.100 Uiso 1 1 calc R . . C15 C 1.03628(18) 0.5071(2) 0.09702(12) 0.0577(6) Uani 1 1 d . . . H13A H 1.0853 0.4874 0.1379 0.087 Uiso 1 1 calc R . . H13B H 1.0663 0.5489 0.0719 0.087 Uiso 1 1 calc R . . H13C H 1.0090 0.4482 0.0715 0.087 Uiso 1 1 calc R . . C9 C 0.68303(16) 0.45017(17) 0.19050(14) 0.0532(6) Uani 1 1 d . . . H14 H 0.6427 0.4988 0.1636 0.064 Uiso 1 1 calc R . . C8 C 0.64454(17) 0.38176(19) 0.22439(16) 0.0677(8) Uani 1 1 d . . . H15 H 0.5777 0.3846 0.2201 0.081 Uiso 1 1 calc R . . C7 C 0.70285(16) 0.30961(17) 0.26438(13) 0.0534(6) Uani 1 1 d . . . H16 H 0.6754 0.2644 0.2870 0.064 Uiso 1 1 calc R . . C1 C 1.0777(3) 0.0048(3) 0.4301(3) 0.136(2) Uani 1 1 d . . . H17A H 1.0583 -0.0381 0.3917 0.204 Uiso 1 1 calc R . . H17B H 1.0290 0.0015 0.4525 0.204 Uiso 1 1 calc R . . H17C H 1.1405 -0.0169 0.4599 0.204 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0415(8) 0.0473(9) 0.0761(11) 0.0259(8) -0.0007(8) -0.0092(7) O5 0.0923(14) 0.0735(12) 0.0713(12) 0.0412(10) 0.0420(11) 0.0317(11) O2 0.0410(8) 0.0433(8) 0.0753(11) 0.0154(7) 0.0112(7) -0.0136(7) O3 0.0511(9) 0.0323(7) 0.0628(9) 0.0106(6) 0.0295(7) 0.0147(6) O4 0.0629(12) 0.1076(16) 0.0508(10) -0.0024(10) 0.0016(9) -0.0015(11) N1 0.0355(9) 0.0352(9) 0.0479(9) 0.0087(7) 0.0114(7) -0.0093(7) N2 0.0410(9) 0.0346(8) 0.0443(9) 0.0101(7) 0.0217(7) 0.0119(7) C3 0.085(2) 0.145(4) 0.177(4) 0.076(3) 0.061(3) 0.051(3) C4 0.0407(12) 0.0691(17) 0.0874(19) 0.0339(15) -0.0049(12) -0.0067(12) C5 0.0384(10) 0.0354(10) 0.0420(10) 0.0042(8) 0.0113(8) -0.0064(8) C6 0.0327(9) 0.0296(9) 0.0412(9) -0.0026(7) 0.0121(8) -0.0031(7) C11 0.0312(9) 0.0323(9) 0.0379(9) -0.0008(7) 0.0142(7) -0.0002(7) C10 0.0359(10) 0.0290(9) 0.0429(10) -0.0016(7) 0.0153(8) 0.0022(8) C12 0.0357(9) 0.0296(9) 0.0378(9) -0.0001(7) 0.0136(7) 0.0066(8) C13 0.0377(10) 0.0436(11) 0.0379(10) 0.0077(8) 0.0174(8) 0.0056(8) C16 0.0436(11) 0.0594(13) 0.0420(11) 0.0109(10) 0.0213(9) 0.0162(10) C17 0.156(4) 0.155(4) 0.077(2) 0.076(2) 0.067(2) 0.103(3) C2 0.106(3) 0.146(4) 0.101(3) 0.014(3) -0.040(2) -0.015(3) C14 0.0717(17) 0.0712(17) 0.0648(16) -0.0118(13) 0.0322(13) -0.0239(14) C15 0.0467(12) 0.0789(17) 0.0549(13) 0.0194(12) 0.0266(11) 0.0217(12) C9 0.0372(11) 0.0397(12) 0.0832(16) 0.0127(11) 0.0200(11) 0.0073(9) C8 0.0335(11) 0.0575(15) 0.117(2) 0.0222(15) 0.0307(13) 0.0047(11) C7 0.0397(11) 0.0452(12) 0.0807(16) 0.0138(11) 0.0270(11) -0.0041(10) C1 0.071(2) 0.095(3) 0.198(5) 0.093(3) -0.017(3) -0.0035(19) _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 1.333(2) . ? O1 C4 1.481(3) . ? O5 C16 1.322(3) . ? O5 C17 1.452(4) . ? O2 C5 1.202(2) . ? O3 C12 1.234(2) . ? O4 C16 1.186(3) . ? N1 C5 1.350(3) . ? N1 C6 1.403(2) . ? N1 H1 0.8600 . ? N2 C12 1.341(2) . ? N2 C13 1.464(2) . ? N2 H2 0.8600 . ? C3 C4 1.474(5) . ? C3 H1A 0.9600 . ? C3 H1B 0.9600 . ? C3 H1C 0.9600 . ? C4 C2 1.491(6) . ? C4 C1 1.506(4) . ? C6 C7 1.384(3) . ? C6 C11 1.389(3) . ? C11 C10 1.387(3) . ? C11 H5 0.9300 . ? C10 C9 1.390(3) . ? C10 C12 1.496(3) . ? C13 C14 1.515(3) . ? C13 C16 1.526(3) . ? C13 C15 1.531(3) . ? C17 H10A 0.9600 . ? C17 H10B 0.9600 . ? C17 H10C 0.9600 . ? C2 H11A 0.9600 . ? C2 H11B 0.9600 . ? C2 H11C 0.9600 . ? C14 H12A 0.9600 . ? C14 H12B 0.9600 . ? C14 H12C 0.9600 . ? C15 H13A 0.9600 . ? C15 H13B 0.9600 . ? C15 H13C 0.9600 . ? C9 C8 1.378(3) . ? C9 H14 0.9300 . ? C8 C7 1.371(3) . ? C8 H15 0.9300 . ? C7 H16 0.9300 . ? C1 H17A 0.9600 . ? C1 H17B 0.9600 . ? C1 H17C 0.9600 . ? 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 C5 O1 C4 122.15(17) . . ? C16 O5 C17 115.5(3) . . ? C5 N1 C6 126.32(15) . . ? C5 N1 H1 116.8 . . ? C6 N1 H1 116.8 . . ? C12 N2 C13 122.86(15) . . ? C12 N2 H2 118.6 . . ? C13 N2 H2 118.6 . . ? C4 C3 H1A 109.5 . . ? C4 C3 H1B 109.5 . . ? H1A C3 H1B 109.5 . . ? C4 C3 H1C 109.5 . . ? H1A C3 H1C 109.5 . . ? H1B C3 H1C 109.5 . . ? C3 C4 O1 111.6(3) . . ? C3 C4 C2 112.4(4) . . ? O1 C4 C2 108.3(3) . . ? C3 C4 C1 111.0(4) . . ? O1 C4 C1 102.1(2) . . ? C2 C4 C1 111.0(4) . . ? O2 C5 O1 125.17(19) . . ? O2 C5 N1 125.79(18) . . ? O1 C5 N1 109.04(16) . . ? C7 C6 C11 119.08(18) . . ? C7 C6 N1 117.58(17) . . ? C11 C6 N1 123.29(16) . . ? C10 C11 C6 120.51(17) . . ? C10 C11 H5 119.7 . . ? C6 C11 H5 119.7 . . ? C11 C10 C9 119.88(18) . . ? C11 C10 C12 122.08(16) . . ? C9 C10 C12 118.04(17) . . ? O3 C12 N2 121.53(17) . . ? O3 C12 C10 120.91(16) . . ? N2 C12 C10 117.55(15) . . ? N2 C13 C14 110.67(17) . . ? N2 C13 C16 108.15(17) . . ? C14 C13 C16 114.3(2) . . ? N2 C13 C15 107.76(16) . . ? C14 C13 C15 110.1(2) . . ? C16 C13 C15 105.59(16) . . ? O4 C16 O5 124.1(2) . . ? O4 C16 C13 123.9(2) . . ? O5 C16 C13 111.8(2) . . ? O5 C17 H10A 109.5 . . ? O5 C17 H10B 109.5 . . ? H10A C17 H10B 109.5 . . ? O5 C17 H10C 109.5 . . ? H10A C17 H10C 109.5 . . ? H10B C17 H10C 109.5 . . ? C4 C2 H11A 109.5 . . ? C4 C2 H11B 109.5 . . ? H11A C2 H11B 109.5 . . ? C4 C2 H11C 109.5 . . ? H11A C2 H11C 109.5 . . ? H11B C2 H11C 109.5 . . ? C13 C14 H12A 109.5 . . ? C13 C14 H12B 109.5 . . ? H12A C14 H12B 109.5 . . ? C13 C14 H12C 109.5 . . ? H12A C14 H12C 109.5 . . ? H12B C14 H12C 109.5 . . ? C13 C15 H13A 109.5 . . ? C13 C15 H13B 109.5 . . ? H13A C15 H13B 109.5 . . ? C13 C15 H13C 109.5 . . ? H13A C15 H13C 109.5 . . ? H13B C15 H13C 109.5 . . ? C8 C9 C10 119.0(2) . . ? C8 C9 H14 120.5 . . ? C10 C9 H14 120.5 . . ? C7 C8 C9 121.3(2) . . ? C7 C8 H15 119.3 . . ? C9 C8 H15 119.3 . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H16 119.9 . . ? C6 C7 H16 119.9 . . ? C4 C1 H17A 109.5 . . ? C4 C1 H17B 109.5 . . ? H17A C1 H17B 109.5 . . ? C4 C1 H17C 109.5 . . ? H17A C1 H17C 109.5 . . ? H17B C1 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.234 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.050