####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 668132' _audit_creation_date 2007-08-14T10:43:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H27 N3 O4' _chemical_formula_sum 'C17 H27 N3 O4' _chemical_formula_weight 337.42 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.1826(8) _cell_length_b 9.5473(7) _cell_length_c 10.2926(11) _cell_angle_alpha 90 _cell_angle_beta 103.133(3) _cell_angle_gamma 90 _cell_volume 974.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4334 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 23.19 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.15 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_unetI/netI 0.0466 _diffrn_reflns_number 4334 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 23.19 _diffrn_reflns_theta_full 23.19 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 1461 _reflns_number_gt 1003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski &Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski &Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1010P)^2^+0.3030P] 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_number_reflns 1461 _refine_ls_number_parameters 219 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1654 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.223 _refine_diff_density_min -0.16 _refine_diff_density_rms 0.043 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.0413(8) 0.6003(9) 0.8205(8) 0.098(2) Uani 1 1 d . . . C2 C 0.0334(9) 0.5522(14) 0.6813(10) 0.140(4) Uani 1 1 d . . . H2A H 0.1218 0.5544 0.6631 0.182 Uiso 1 1 calc R . . H2B H -0.0256 0.613 0.6201 0.182 Uiso 1 1 calc R . . H2C H -0.0011 0.4583 0.6709 0.182 Uiso 1 1 calc R . . C3 C -0.0721(8) 0.6968(13) 0.8297(15) 0.166(5) Uani 1 1 d . . . H3A H -0.0367 0.7785 0.88 0.216 Uiso 1 1 calc R . . H3B H -0.1334 0.6496 0.8733 0.216 Uiso 1 1 calc R . . H3C H -0.1189 0.7243 0.7416 0.216 Uiso 1 1 calc R . . C4 C 0.0513(11) 0.4779(13) 0.9167(12) 0.165(5) Uani 1 1 d . . . H4A H 0.1399 0.4757 0.9742 0.215 Uiso 1 1 calc R . . H4B H 0.0351 0.392 0.8672 0.215 Uiso 1 1 calc R . . H4C H -0.0146 0.4886 0.9694 0.215 Uiso 1 1 calc R . . O1 O 0.1611(5) 0.6911(5) 0.8645(5) 0.0929(15) Uani 1 1 d . . . C5 C 0.2862(7) 0.6435(7) 0.8772(7) 0.0748(18) Uani 1 1 d . . . O2 O 0.3154(5) 0.5256(5) 0.8478(5) 0.1015(16) Uani 1 1 d . . . N1 N 0.3759(5) 0.7439(6) 0.9224(6) 0.0802(16) Uani 1 1 d . . . H1 H 0.3474 0.8219 0.9474 0.104 Uiso 1 1 calc R . . C6 C 0.5186(6) 0.7278(7) 0.9313(6) 0.0764(18) Uani 1 1 d . . . H6 H 0.5329 0.6352 0.8958 0.099 Uiso 1 1 calc R . . C7 C 0.5690(7) 0.8349(9) 0.8483(7) 0.090(2) Uani 1 1 d . . . H7A H 0.5435 0.9284 0.87 0.117 Uiso 1 1 calc R . . H7B H 0.6664 0.8304 0.8628 0.117 Uiso 1 1 calc R . . O3 O 0.5071(9) 0.8007(9) 0.7141(6) 0.159(3) Uani 1 1 d . . . C8 C 0.4801(12) 0.8949(12) 0.6271(11) 0.144(4) Uani 1 1 d . . . H8A H 0.5636 0.9362 0.6152 0.187 Uiso 1 1 calc R . . H8B H 0.4284 0.9678 0.6582 0.187 Uiso 1 1 calc R . . C9 C 0.4020(9) 0.8418(11) 0.4957(8) 0.105(3) Uani 1 1 d . . . C10 C 0.4008(9) 0.9167(12) 0.3807(9) 0.119(3) Uani 1 1 d . . . H10 H 0.4483 1.0004 0.3853 0.154 Uiso 1 1 calc R . . C11 C 0.3309(13) 0.8689(18) 0.2618(10) 0.139(4) Uani 1 1 d . . . H11 H 0.3327 0.9202 0.1854 0.18 Uiso 1 1 calc R . . C12 C 0.2593(12) 0.7507(17) 0.2498(13) 0.139(4) Uani 1 1 d . . . H12 H 0.2139 0.7192 0.1661 0.181 Uiso 1 1 calc R . . C13 C 0.2534(11) 0.6750(15) 0.3638(14) 0.143(4) Uani 1 1 d . . . H13 H 0.2001 0.5951 0.3582 0.186 Uiso 1 1 calc R . . C14 C 0.3274(9) 0.7206(12) 0.4844(9) 0.115(3) Uani 1 1 d . . . H14 H 0.3273 0.6683 0.5605 0.149 Uiso 1 1 calc R . . N2 N 0.5932(6) 0.7327(6) 1.0693(5) 0.0838(16) Uani 1 1 d . . . H2 H 0.5797 0.7996 1.1206 0.109 Uiso 1 1 calc R . . C15 C 0.6848(6) 0.6301(7) 1.1169(7) 0.0692(17) Uani 1 1 d . . . O4 O 0.7027(5) 0.5315(5) 1.0466(5) 0.0855(13) Uani 1 1 d . . . N3 N 0.7528(6) 0.6420(6) 1.2447(6) 0.0905(18) Uani 1 1 d . . . C16 C 0.7132(10) 0.7348(10) 1.3400(8) 0.115(3) Uani 1 1 d . . . H16A H 0.6166 0.7384 1.3234 0.15 Uiso 1 1 calc R . . H16B H 0.7478 0.827 1.3312 0.15 Uiso 1 1 calc R . . H16C H 0.7489 0.7006 1.4287 0.15 Uiso 1 1 calc R . . C17 C 0.8556(9) 0.5367(12) 1.2985(9) 0.130(3) Uani 1 1 d . . . H17A H 0.8819 0.4891 1.2262 0.17 Uiso 1 1 calc R . . H17B H 0.8193 0.4701 1.3509 0.17 Uiso 1 1 calc R . . H17C H 0.9328 0.5818 1.3535 0.17 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 C1 0.086(5) 0.091(5) 0.107(6) -0.005(5) 0.003(4) -0.024(4) C2 0.108(6) 0.171(9) 0.120(7) -0.048(7) -0.015(5) -0.008(7) C3 0.071(5) 0.142(8) 0.281(15) -0.049(10) 0.033(7) -0.002(6) C4 0.127(9) 0.164(10) 0.178(10) 0.058(9) -0.022(7) -0.062(7) O1 0.073(3) 0.077(3) 0.127(4) -0.018(3) 0.017(3) -0.011(2) C5 0.081(5) 0.062(4) 0.074(4) 0.005(3) 0.001(3) -0.003(4) O2 0.098(3) 0.068(3) 0.120(4) -0.012(3) -0.012(3) 0.003(3) N1 0.074(4) 0.066(3) 0.094(4) -0.012(3) 0.007(3) 0.007(3) C6 0.079(4) 0.067(4) 0.074(4) -0.008(4) -0.003(3) 0.006(3) C7 0.085(5) 0.110(6) 0.066(4) -0.001(4) -0.002(4) 0.003(4) O3 0.225(8) 0.144(5) 0.080(4) 0.015(4) -0.023(4) -0.016(6) C8 0.175(10) 0.113(7) 0.119(8) 0.032(7) -0.015(7) -0.024(7) C9 0.108(6) 0.130(8) 0.071(5) 0.003(5) 0.010(4) 0.010(6) C10 0.125(7) 0.141(8) 0.089(7) 0.010(6) 0.021(5) 0.020(6) C11 0.146(10) 0.195(13) 0.075(7) 0.018(8) 0.023(6) 0.068(9) C12 0.114(8) 0.184(12) 0.102(9) -0.037(9) -0.013(6) 0.037(8) C13 0.115(8) 0.165(10) 0.134(9) -0.020(8) -0.003(7) -0.005(7) C14 0.108(6) 0.129(8) 0.098(6) 0.018(6) 0.003(5) 0.005(6) N2 0.102(4) 0.074(3) 0.065(3) -0.005(3) -0.004(3) 0.018(3) C15 0.069(4) 0.064(4) 0.068(4) 0.005(4) 0.001(3) -0.007(3) O4 0.088(3) 0.073(3) 0.090(3) 0.001(3) 0.009(2) 0.007(3) N3 0.097(4) 0.091(4) 0.073(4) 0.012(4) -0.003(3) 0.013(3) C16 0.148(7) 0.112(6) 0.074(5) 0.013(5) 0.000(5) -0.003(6) C17 0.120(7) 0.143(8) 0.106(6) 0.011(6) -0.022(5) 0.040(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.481(9) . ? C1 C2 1.490(12) . ? C1 C3 1.497(13) . ? C1 C4 1.520(13) . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? O1 C5 1.331(8) . ? C5 O2 1.220(8) . ? C5 N1 1.332(8) . ? N1 C6 1.444(8) . ? N1 H1 0.86 . ? C6 N2 1.451(8) . ? C6 C7 1.496(10) . ? C6 H6 0.98 . ? C7 O3 1.420(9) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? O3 C8 1.255(11) . ? C8 C9 1.492(13) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C14 1.374(13) . ? C9 C10 1.380(12) . ? C10 C11 1.348(16) . ? C10 H10 0.93 . ? C11 C12 1.334(17) . ? C11 H11 0.93 . ? C12 C13 1.391(16) . ? C12 H12 0.93 . ? C13 C14 1.368(13) . ? C13 H13 0.93 . ? C14 H14 0.93 . ? N2 C15 1.364(8) . ? N2 H2 0.86 . ? C15 O4 1.225(7) . ? C15 N3 1.345(8) . ? N3 C16 1.446(11) . ? N3 C17 1.466(10) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? 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 O1 C1 C2 109.6(7) . . ? O1 C1 C3 102.4(7) . . ? C2 C1 C3 112.1(8) . . ? O1 C1 C4 108.8(6) . . ? C2 C1 C4 111.7(9) . . ? C3 C1 C4 111.8(10) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 O1 C1 122.3(6) . . ? O2 C5 O1 124.9(6) . . ? O2 C5 N1 124.3(7) . . ? O1 C5 N1 110.7(6) . . ? C5 N1 C6 123.1(6) . . ? C5 N1 H1 118.5 . . ? C6 N1 H1 118.5 . . ? N1 C6 N2 110.7(6) . . ? N1 C6 C7 111.2(5) . . ? N2 C6 C7 111.5(5) . . ? N1 C6 H6 107.7 . . ? N2 C6 H6 107.7 . . ? C7 C6 H6 107.7 . . ? O3 C7 C6 105.3(6) . . ? O3 C7 H7A 110.7 . . ? C6 C7 H7A 110.7 . . ? O3 C7 H7B 110.7 . . ? C6 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? C8 O3 C7 120.4(9) . . ? O3 C8 C9 112.9(9) . . ? O3 C8 H8A 109 . . ? C9 C8 H8A 109 . . ? O3 C8 H8B 109 . . ? C9 C8 H8B 109 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 117.8(8) . . ? C14 C9 C8 122.2(9) . . ? C10 C9 C8 120.0(9) . . ? C11 C10 C9 120.2(12) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 122.3(12) . . ? C12 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C11 C12 C13 119.3(11) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 118.6(11) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C9 121.7(10) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? C15 N2 C6 119.4(6) . . ? C15 N2 H2 120.3 . . ? C6 N2 H2 120.3 . . ? O4 C15 N3 122.0(6) . . ? O4 C15 N2 121.4(6) . . ? N3 C15 N2 116.7(6) . . ? C15 N3 C16 123.7(6) . . ? C15 N3 C17 118.4(7) . . ? C16 N3 C17 116.7(6) . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 O1 C5 -64.1(9) . . . . ? C3 C1 O1 C5 176.8(8) . . . . ? C4 C1 O1 C5 58.3(10) . . . . ? C1 O1 C5 O2 4.3(11) . . . . ? C1 O1 C5 N1 -177.8(6) . . . . ? O2 C5 N1 C6 5.3(11) . . . . ? O1 C5 N1 C6 -172.6(6) . . . . ? C5 N1 C6 N2 -115.4(7) . . . . ? C5 N1 C6 C7 120.1(7) . . . . ? N1 C6 C7 O3 -67.0(8) . . . . ? N2 C6 C7 O3 168.9(6) . . . . ? C6 C7 O3 C8 149.4(10) . . . . ? C7 O3 C8 C9 -173.7(8) . . . . ? O3 C8 C9 C14 22.0(16) . . . . ? O3 C8 C9 C10 -159.4(10) . . . . ? C14 C9 C10 C11 -1.7(14) . . . . ? C8 C9 C10 C11 179.7(10) . . . . ? C9 C10 C11 C12 1.1(16) . . . . ? C10 C11 C12 C13 1.5(17) . . . . ? C11 C12 C13 C14 -3.5(16) . . . . ? C12 C13 C14 C9 3.0(15) . . . . ? C10 C9 C14 C13 -0.4(14) . . . . ? C8 C9 C14 C13 178.2(10) . . . . ? N1 C6 N2 C15 129.8(6) . . . . ? C7 C6 N2 C15 -105.7(7) . . . . ? C6 N2 C15 O4 -2.2(10) . . . . ? C6 N2 C15 N3 178.6(6) . . . . ? O4 C15 N3 C16 -164.2(7) . . . . ? N2 C15 N3 C16 14.9(10) . . . . ? O4 C15 N3 C17 2.9(10) . . . . ? N2 C15 N3 C17 -177.9(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.86 2.07 2.898(7) 161.6 2_657 N2 H2 O2 0.86 2.4 3.009(8) 128.6 2_657 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 668133' _audit_creation_date 2007-08-16T10:29:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H32 N4 O3' _chemical_formula_sum 'C17 H32 N4 O3' _chemical_formula_weight 340.47 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.1850(12) _cell_length_b 9.4470(7) _cell_length_c 10.571(2) _cell_angle_alpha 90 _cell_angle_beta 103.216(4) _cell_angle_gamma 90 _cell_volume 990.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15610 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_unetI/netI 0.0385 _diffrn_reflns_number 15610 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 1857 _reflns_number_gt 1321 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0716P)^2^+0.0961P] 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_number_reflns 1857 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_ref 0.125 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.189 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.028 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 C1 C 0.0833(4) 0.6865(5) 0.3666(4) 0.0757(11) Uani 1 1 d . . . C2 C 0.1135(7) 0.7496(11) 0.2446(5) 0.173(4) Uani 1 1 d . . . H2A H 0.2084 0.7421 0.2485 0.26 Uiso 1 1 calc R . . H2B H 0.0874 0.8475 0.2381 0.26 Uiso 1 1 calc R . . H2C H 0.064 0.6993 0.17 0.26 Uiso 1 1 calc R . . C3 C 0.1140(5) 0.5279(6) 0.3766(5) 0.1171(19) Uani 1 1 d . . . H3A H 0.0889 0.49 0.452 0.176 Uiso 1 1 calc R . . H3B H 0.2087 0.5131 0.3837 0.176 Uiso 1 1 calc R . . H3C H 0.0636 0.4809 0.3002 0.176 Uiso 1 1 calc R . . C4 C -0.0686(4) 0.7020(6) 0.3582(5) 0.1035(16) Uani 1 1 d . . . H4A H -0.0901 0.6614 0.4343 0.155 Uiso 1 1 calc R . . H4B H -0.1182 0.6537 0.2824 0.155 Uiso 1 1 calc R . . H4C H -0.0924 0.8005 0.3529 0.155 Uiso 1 1 calc R . . C5 C 0.1615(4) 0.7746(4) 0.4817(4) 0.0653(10) Uani 1 1 d . . . O1 O 0.2055(3) 0.8930(3) 0.4648(3) 0.0863(8) Uani 1 1 d . . . N1 N 0.1870(3) 0.7247(3) 0.6050(3) 0.0582(7) Uani 1 1 d . . . C6 C 0.2650(3) 0.8139(4) 0.7083(3) 0.0623(9) Uani 1 1 d . . . H6 H 0.2185 0.9047 0.7084 0.075 Uiso 1 1 calc R . . C7 C 0.2602(4) 0.7336(5) 0.8322(4) 0.0800(12) Uani 1 1 d . . . H7A H 0.3378 0.6718 0.858 0.096 Uiso 1 1 calc R . . H7B H 0.2581 0.7985 0.9028 0.096 Uiso 1 1 calc R . . C8 C 0.1333(4) 0.6502(6) 0.7971(4) 0.0917(13) Uani 1 1 d . . . H8A H 0.0561 0.708 0.8025 0.11 Uiso 1 1 calc R . . H8B H 0.1368 0.569 0.854 0.11 Uiso 1 1 calc R . . C9 C 0.1258(4) 0.6041(5) 0.6597(4) 0.0754(11) Uani 1 1 d . . . H9A H 0.1766 0.5178 0.657 0.091 Uiso 1 1 calc R . . H9B H 0.0331 0.5893 0.6131 0.091 Uiso 1 1 calc R . . C10 C 0.4087(4) 0.8416(4) 0.6971(3) 0.0577(9) Uani 1 1 d . . . O2 O 0.4632(3) 0.9540(3) 0.7368(3) 0.0817(8) Uani 1 1 d . . . N2 N 0.4726(3) 0.7364(3) 0.6519(3) 0.0537(7) Uani 1 1 d . . . H2 H 0.4308 0.6574 0.6325 0.064 Uiso 1 1 calc R . . C11 C 0.6110(3) 0.7490(4) 0.6336(3) 0.0523(8) Uani 1 1 d . . . H11 H 0.6402 0.8475 0.6496 0.063 Uiso 1 1 calc R . . C12 C 0.7078(3) 0.6547(4) 0.7278(3) 0.0601(9) Uani 1 1 d . . . H12A H 0.7973 0.6659 0.7118 0.072 Uiso 1 1 calc R . . H12B H 0.6811 0.557 0.7093 0.072 Uiso 1 1 calc R . . C13 C 0.7159(4) 0.6832(4) 0.8724(3) 0.0693(10) Uani 1 1 d . . . H13 H 0.6242 0.6791 0.8866 0.083 Uiso 1 1 calc R . . C14 C 0.7740(5) 0.8284(6) 0.9149(4) 0.0929(14) Uani 1 1 d . . . H14A H 0.7763 0.8419 1.0054 0.139 Uiso 1 1 calc R . . H14B H 0.7184 0.9001 0.8648 0.139 Uiso 1 1 calc R . . H14C H 0.8638 0.835 0.9013 0.139 Uiso 1 1 calc R . . C15 C 0.7993(5) 0.5676(6) 0.9549(4) 0.0997(16) Uani 1 1 d . . . H15A H 0.7611 0.4767 0.9276 0.149 Uiso 1 1 calc R . . H15B H 0.7988 0.5824 1.0447 0.149 Uiso 1 1 calc R . . H15C H 0.8904 0.5713 0.9444 0.149 Uiso 1 1 calc R . . N3 N 0.6151(3) 0.7131(3) 0.5027(3) 0.0603(7) Uani 1 1 d . . . H3 H 0.6376 0.6284 0.4863 0.072 Uiso 1 1 calc R . . C16 C 0.5846(3) 0.8079(4) 0.4033(3) 0.0537(8) Uani 1 1 d . . . O3 O 0.5773(3) 0.9361(2) 0.4234(2) 0.0692(7) Uani 1 1 d . . . N4 N 0.5685(3) 0.7530(3) 0.2837(3) 0.0687(8) Uani 1 1 d . . . H4 H 0.5765 0.6629 0.2759 0.082 Uiso 1 1 calc R . . C17 C 0.5389(5) 0.8372(5) 0.1694(4) 0.0928(13) Uani 1 1 d . . . H17A H 0.5115 0.7772 0.0947 0.139 Uiso 1 1 calc R . . H17B H 0.6178 0.8896 0.1626 0.139 Uiso 1 1 calc R . . H17C H 0.4673 0.9019 0.1736 0.139 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 C1 0.074(3) 0.072(3) 0.075(3) -0.004(2) 0.0044(19) 0.005(2) C2 0.199(7) 0.243(10) 0.071(3) -0.006(5) 0.018(3) -0.097(7) C3 0.123(4) 0.095(4) 0.114(4) -0.032(3) -0.013(3) 0.041(3) C4 0.081(3) 0.077(3) 0.133(4) -0.019(3) -0.015(3) 0.009(2) C5 0.059(2) 0.063(3) 0.074(2) 0.006(2) 0.0146(17) 0.0083(19) O1 0.101(2) 0.0625(19) 0.0917(19) 0.0149(15) 0.0134(15) -0.0090(16) N1 0.0541(15) 0.0497(16) 0.0700(19) -0.0020(16) 0.0127(13) -0.0032(14) C6 0.060(2) 0.050(2) 0.076(2) -0.0113(18) 0.0156(17) 0.0062(17) C7 0.082(3) 0.092(3) 0.069(2) -0.013(2) 0.0233(19) 0.000(2) C8 0.091(3) 0.103(4) 0.085(3) 0.014(3) 0.028(2) -0.004(3) C9 0.068(2) 0.064(2) 0.096(3) 0.007(2) 0.020(2) -0.0108(19) C10 0.065(2) 0.0386(19) 0.069(2) -0.0050(17) 0.0144(17) -0.0003(17) O2 0.0758(17) 0.0442(15) 0.125(2) -0.0241(15) 0.0220(15) -0.0088(13) N2 0.0556(15) 0.0353(14) 0.0706(17) -0.0058(13) 0.0150(12) -0.0042(12) C11 0.0550(19) 0.0433(18) 0.058(2) -0.0048(15) 0.0125(14) -0.0064(15) C12 0.0521(19) 0.063(2) 0.063(2) 0.0028(17) 0.0088(15) -0.0009(16) C13 0.067(2) 0.080(3) 0.061(2) 0.000(2) 0.0136(17) -0.008(2) C14 0.110(3) 0.095(3) 0.072(3) -0.011(2) 0.015(2) -0.014(3) C15 0.111(4) 0.099(4) 0.078(3) 0.020(3) -0.001(3) -0.012(3) N3 0.0807(19) 0.0405(15) 0.0617(17) 0.0021(15) 0.0203(13) 0.0040(14) C16 0.0515(19) 0.045(2) 0.063(2) 0.0028(18) 0.0094(15) -0.0044(15) O3 0.0923(17) 0.0385(15) 0.0716(15) 0.0034(12) 0.0081(12) -0.0001(13) N4 0.099(2) 0.0486(17) 0.0565(18) -0.0025(15) 0.0138(15) 0.0015(16) C17 0.128(4) 0.083(3) 0.062(3) 0.003(2) 0.010(2) 0.007(3) _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 C1 C2 1.515(7) . ? C1 C3 1.529(7) . ? C1 C4 1.536(6) . ? C1 C5 1.538(6) . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C5 O1 1.233(5) . ? C5 N1 1.353(5) . ? N1 C6 1.462(4) . ? N1 C9 1.478(5) . ? C6 C10 1.517(5) . ? C6 C7 1.525(5) . ? C6 H6 0.98 . ? C7 C8 1.487(6) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.502(6) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 O2 1.228(4) . ? C10 N2 1.335(4) . ? N2 C11 1.471(4) . ? N2 H2 0.86 . ? C11 N3 1.435(4) . ? C11 C12 1.520(4) . ? C11 H11 0.98 . ? C12 C13 1.535(5) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.521(7) . ? C13 C15 1.528(6) . ? C13 H13 0.98 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? N3 C16 1.361(4) . ? N3 H3 0.86 . ? C16 O3 1.234(4) . ? C16 N4 1.342(4) . ? N4 C17 1.421(5) . ? N4 H4 0.86 . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 111.5(5) . . ? C2 C1 C4 108.2(4) . . ? C3 C1 C4 106.5(4) . . ? C2 C1 C5 106.9(4) . . ? C3 C1 C5 114.5(4) . . ? C4 C1 C5 109.0(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C5 N1 117.4(4) . . ? O1 C5 C1 121.0(4) . . ? N1 C5 C1 121.6(3) . . ? C5 N1 C6 118.0(3) . . ? C5 N1 C9 129.8(3) . . ? C6 N1 C9 111.0(3) . . ? N1 C6 C10 114.2(3) . . ? N1 C6 C7 103.7(3) . . ? C10 C6 C7 111.9(3) . . ? N1 C6 H6 108.9 . . ? C10 C6 H6 108.9 . . ? C7 C6 H6 108.9 . . ? C8 C7 C6 104.3(3) . . ? C8 C7 H7A 110.9 . . ? C6 C7 H7A 110.9 . . ? C8 C7 H7B 110.9 . . ? C6 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C7 C8 C9 104.1(3) . . ? C7 C8 H8A 110.9 . . ? C9 C8 H8A 110.9 . . ? C7 C8 H8B 110.9 . . ? C9 C8 H8B 110.9 . . ? H8A C8 H8B 108.9 . . ? N1 C9 C8 102.9(3) . . ? N1 C9 H9A 111.2 . . ? C8 C9 H9A 111.2 . . ? N1 C9 H9B 111.2 . . ? C8 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? O2 C10 N2 123.2(3) . . ? O2 C10 C6 119.4(3) . . ? N2 C10 C6 117.3(3) . . ? C10 N2 C11 123.2(3) . . ? C10 N2 H2 118.4 . . ? C11 N2 H2 118.4 . . ? N3 C11 N2 110.4(2) . . ? N3 C11 C12 109.6(3) . . ? N2 C11 C12 111.3(3) . . ? N3 C11 H11 108.5 . . ? N2 C11 H11 108.5 . . ? C12 C11 H11 108.5 . . ? C11 C12 C13 115.4(3) . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C15 110.4(3) . . ? C14 C13 C12 112.4(3) . . ? C15 C13 C12 109.9(3) . . ? C14 C13 H13 108 . . ? C15 C13 H13 108 . . ? C12 C13 H13 108 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C16 N3 C11 122.4(3) . . ? C16 N3 H3 118.8 . . ? C11 N3 H3 118.8 . . ? O3 C16 N4 122.8(3) . . ? O3 C16 N3 121.7(3) . . ? N4 C16 N3 115.4(3) . . ? C16 N4 C17 122.7(3) . . ? C16 N4 H4 118.6 . . ? C17 N4 H4 118.6 . . ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C5 O1 17.4(6) . . . . ? C3 C1 C5 O1 141.4(4) . . . . ? C4 C1 C5 O1 -99.3(5) . . . . ? C2 C1 C5 N1 -161.4(5) . . . . ? C3 C1 C5 N1 -37.3(5) . . . . ? C4 C1 C5 N1 81.9(5) . . . . ? O1 C5 N1 C6 -0.4(5) . . . . ? C1 C5 N1 C6 178.5(3) . . . . ? O1 C5 N1 C9 165.6(3) . . . . ? C1 C5 N1 C9 -15.5(6) . . . . ? C5 N1 C6 C10 -64.1(4) . . . . ? C9 N1 C6 C10 127.4(3) . . . . ? C5 N1 C6 C7 173.8(3) . . . . ? C9 N1 C6 C7 5.3(4) . . . . ? N1 C6 C7 C8 -26.5(4) . . . . ? C10 C6 C7 C8 -150.0(3) . . . . ? C6 C7 C8 C9 37.8(4) . . . . ? C5 N1 C9 C8 -149.3(4) . . . . ? C6 N1 C9 C8 17.5(4) . . . . ? C7 C8 C9 N1 -33.8(4) . . . . ? N1 C6 C10 O2 148.8(3) . . . . ? C7 C6 C10 O2 -93.9(4) . . . . ? N1 C6 C10 N2 -35.8(4) . . . . ? C7 C6 C10 N2 81.6(4) . . . . ? O2 C10 N2 C11 -5.9(5) . . . . ? C6 C10 N2 C11 178.8(3) . . . . ? C10 N2 C11 N3 -125.5(3) . . . . ? C10 N2 C11 C12 112.6(3) . . . . ? N3 C11 C12 C13 179.0(3) . . . . ? N2 C11 C12 C13 -58.6(4) . . . . ? C11 C12 C13 C14 -65.3(4) . . . . ? C11 C12 C13 C15 171.4(3) . . . . ? N2 C11 N3 C16 83.7(4) . . . . ? C12 C11 N3 C16 -153.4(3) . . . . ? C11 N3 C16 O3 14.3(5) . . . . ? C11 N3 C16 N4 -168.1(3) . . . . ? O3 C16 N4 C17 -1.3(5) . . . . ? N3 C16 N4 C17 -178.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.86 2.17 2.959(3) 152.5 2_646 N3 H3 O2 0.86 2.87 3.480(4) 129.6 2_646 N4 H4 O2 0.86 2.01 2.845(4) 162.6 2_646 data_import _database_code_depnum_ccdc_archive 'CCDC 668134' _audit_creation_date 2007-04-26T12:34:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H25 N3 O3' _chemical_formula_sum 'C13 H25 N3 O3' _chemical_formula_weight 271.36 _chemical_compound_source 'synthesis as described' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4284(2) _cell_length_b 15.8240(3) _cell_length_c 21.0020(5) _cell_angle_alpha 90 _cell_angle_beta 98.536(2) _cell_angle_gamma 90 _cell_volume 3098.68(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11307 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.5 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_unetI/netI 0.0524 _diffrn_reflns_number 11307 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5770 _reflns_number_gt 2996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0868P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5770 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.128 _refine_ls_goodness_of_fit_ref 0.95 _refine_ls_restrained_S_all 0.95 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.205 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.059 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.4704(2) -0.06249(14) 0.64364(11) 0.0668(6) Uani 1 1 d . . . C2 C 0.5832(3) -0.07793(17) 0.70134(13) 0.0978(9) Uani 1 1 d . . . H2A H 0.551 -0.0555 0.7392 0.147 Uiso 1 1 calc R . . H2B H 0.6708 -0.0505 0.695 0.147 Uiso 1 1 calc R . . H2C H 0.5995 -0.1376 0.7066 0.147 Uiso 1 1 calc R . . C3 C 0.3247(3) -0.09645(18) 0.65344(16) 0.1161(11) Uani 1 1 d . . . H3A H 0.2561 -0.0846 0.616 0.174 Uiso 1 1 calc R . . H3B H 0.2949 -0.0698 0.6903 0.174 Uiso 1 1 calc R . . H3C H 0.331 -0.1564 0.6602 0.174 Uiso 1 1 calc R . . C4 C 0.5158(3) -0.09650(17) 0.58299(13) 0.0967(9) Uani 1 1 d . . . H4A H 0.4421 -0.0855 0.5473 0.145 Uiso 1 1 calc R . . H4B H 0.5313 -0.1563 0.5872 0.145 Uiso 1 1 calc R . . H4C H 0.6031 -0.0694 0.5757 0.145 Uiso 1 1 calc R . . O1 O 0.46570(14) 0.03043(9) 0.64155(6) 0.0616(4) Uani 1 1 d . . . C5 C 0.3712(2) 0.07148(14) 0.59807(10) 0.0540(5) Uani 1 1 d . . . O2 O 0.29179(15) 0.03908(10) 0.55412(7) 0.0737(5) Uani 1 1 d . . . N1 N 0.37514(16) 0.15512(11) 0.60956(8) 0.0512(4) Uani 1 1 d . . . C6 C 0.47275(19) 0.19853(13) 0.65928(9) 0.0494(5) Uani 1 1 d . . . H6 H 0.5706 0.1774 0.6597 0.059 Uiso 1 1 calc R . . C7 C 0.4624(2) 0.28934(15) 0.63508(12) 0.0720(7) Uani 1 1 d . . . H7A H 0.478 0.3289 0.6707 0.086 Uiso 1 1 calc R . . H7B H 0.5321 0.3001 0.6064 0.086 Uiso 1 1 calc R . . C8 C 0.3117(3) 0.29625(15) 0.59969(13) 0.0788(7) Uani 1 1 d . . . H8A H 0.2434 0.3045 0.6294 0.095 Uiso 1 1 calc R . . H8B H 0.3033 0.3426 0.5692 0.095 Uiso 1 1 calc R . . C9 C 0.2888(2) 0.21318(14) 0.56595(10) 0.0627(6) Uani 1 1 d . . . H9A H 0.1883 0.1972 0.56 0.075 Uiso 1 1 calc R . . H9B H 0.3216 0.2149 0.5243 0.075 Uiso 1 1 calc R . . N2 N 0.42988(15) 0.18697(11) 0.72187(7) 0.0514(4) Uani 1 1 d . . . H2 H 0.3405 0.1911 0.7255 0.062 Uiso 1 1 calc R . . C10 C 0.52486(19) 0.16996(12) 0.77481(10) 0.0479(5) Uani 1 1 d . . . O3 O 0.65595(13) 0.17166(10) 0.77475(7) 0.0662(4) Uani 1 1 d . . . N3 N 0.46720(15) 0.15215(11) 0.82856(8) 0.0561(5) Uani 1 1 d . . . H3 H 0.3753 0.1525 0.8261 0.067 Uiso 1 1 calc R . . C11 C 0.5523(2) 0.13246(14) 0.89017(10) 0.0561(6) Uani 1 1 d . . . H11 H 0.6297 0.1742 0.8982 0.067 Uiso 1 1 calc R . . C12 C 0.4596(2) 0.14132(16) 0.94257(11) 0.0773(7) Uani 1 1 d . . . H12A H 0.4198 0.1972 0.9414 0.116 Uiso 1 1 calc R . . H12B H 0.5167 0.1318 0.9837 0.116 Uiso 1 1 calc R . . H12C H 0.3834 0.1006 0.9359 0.116 Uiso 1 1 calc R . . C13 C 0.6200(3) 0.04573(17) 0.89060(13) 0.0917(8) Uani 1 1 d . . . H13A H 0.6786 0.0424 0.857 0.138 Uiso 1 1 calc R . . H13B H 0.5461 0.0036 0.8836 0.138 Uiso 1 1 calc R . . H13C H 0.6783 0.0362 0.9315 0.138 Uiso 1 1 calc R . . C21 C 0.9341(2) 0.41598(13) 0.64798(11) 0.0621(6) Uani 1 1 d . . . C22 C 1.0540(3) 0.43434(16) 0.70196(13) 0.0922(8) Uani 1 1 d . . . H22A H 1.1437 0.4177 0.6893 0.138 Uiso 1 1 calc R . . H22B H 1.0387 0.4033 0.7396 0.138 Uiso 1 1 calc R . . H22C H 1.056 0.4937 0.7113 0.138 Uiso 1 1 calc R . . C23 C 0.7894(3) 0.43942(18) 0.66562(16) 0.1144(11) Uani 1 1 d . . . H23A H 0.7159 0.427 0.6301 0.172 Uiso 1 1 calc R . . H23B H 0.788 0.4987 0.6753 0.172 Uiso 1 1 calc R . . H23C H 0.7725 0.4075 0.7026 0.172 Uiso 1 1 calc R . . C24 C 0.9621(3) 0.45855(16) 0.58709(13) 0.0988(9) Uani 1 1 d . . . H24A H 0.8845 0.4469 0.5532 0.148 Uiso 1 1 calc R . . H24B H 1.05 0.4375 0.5752 0.148 Uiso 1 1 calc R . . H24C H 0.9698 0.5185 0.594 0.148 Uiso 1 1 calc R . . O21 O 0.94290(14) 0.32399(8) 0.64151(7) 0.0583(4) Uani 1 1 d . . . C25 C 0.8499(2) 0.28143(14) 0.59833(10) 0.0495(5) Uani 1 1 d . B . O22 O 0.76214(14) 0.31286(9) 0.55722(7) 0.0665(4) Uani 1 1 d . . . N21 N 0.86784(16) 0.19709(11) 0.60638(7) 0.0505(4) Uani 1 1 d . . . C26 C 0.97175(19) 0.15584(12) 0.65496(9) 0.0477(5) Uani 1 1 d . B . H26 H 1.0667 0.1812 0.6552 0.057 Uiso 1 1 calc R A 1 C27 C 0.9720(3) 0.06545(14) 0.63008(12) 0.0717(7) Uani 0.522(8) 1 d P B 1 H27A H 1.0449 0.0579 0.6025 0.086 Uiso 0.522(8) 1 calc PR B 1 H27B H 0.9889 0.0255 0.6654 0.086 Uiso 0.522(8) 1 calc PR B 1 C28 C 0.8293(6) 0.0551(3) 0.5940(3) 0.070(2) Uani 0.522(8) 1 d P B 1 H28A H 0.7608 0.042 0.6228 0.084 Uiso 0.522(8) 1 calc PR B 1 H28B H 0.8282 0.0095 0.563 0.084 Uiso 0.522(8) 1 calc PR B 1 C29 C 0.7923(2) 0.13760(14) 0.56024(10) 0.0627(6) Uani 0.522(8) 1 d P B 1 H29A H 0.8275 0.14 0.5192 0.075 Uiso 0.522(8) 1 calc PR B 1 H29B H 0.6897 0.1477 0.5536 0.075 Uiso 0.522(8) 1 calc PR B 1 C47 C 0.9720(3) 0.06545(14) 0.63008(12) 0.0717(7) Uani 0.478(8) 1 d P B 2 H47A H 1.0697 0.0448 0.6332 0.086 Uiso 0.478(8) 1 calc PR B 2 H47B H 0.9198 0.0289 0.6555 0.086 Uiso 0.478(8) 1 calc PR B 2 C48 C 0.9018(8) 0.0654(4) 0.5613(3) 0.076(2) Uani 0.478(8) 1 d P B 2 H48A H 0.8547 0.0119 0.5497 0.091 Uiso 0.478(8) 1 calc PR B 2 H48B H 0.9707 0.0768 0.5324 0.091 Uiso 0.478(8) 1 calc PR B 2 C49 C 0.7923(2) 0.13760(14) 0.56024(10) 0.0627(6) Uani 0.478(8) 1 d P B 2 H49A H 0.7707 0.1625 0.5177 0.075 Uiso 0.478(8) 1 calc PR B 2 H49B H 0.704 0.1182 0.5739 0.075 Uiso 0.478(8) 1 calc PR B 2 N22 N 0.92937(15) 0.16309(10) 0.71827(7) 0.0474(4) Uani 1 1 d . . . H22 H 0.8407 0.1554 0.7221 0.057 Uiso 1 1 calc R B . C30 C 1.02282(19) 0.18134(12) 0.77136(9) 0.0452(5) Uani 1 1 d . B . O23 O 1.15450(13) 0.18374(10) 0.77107(6) 0.0650(4) Uani 1 1 d . . . N23 N 0.96438(15) 0.19559(11) 0.82513(8) 0.0554(5) Uani 1 1 d . . . H23 H 0.8738 0.1875 0.8238 0.066 Uiso 1 1 calc R B . C31 C 1.04703(19) 0.22387(13) 0.88515(9) 0.0522(5) Uani 1 1 d . B . H31 H 1.1356 0.1906 0.8928 0.063 Uiso 1 1 calc R . . C32 C 0.9626(2) 0.20638(16) 0.93940(10) 0.0733(7) Uani 1 1 d . . . H32A H 0.9399 0.1473 0.9401 0.11 Uiso 1 1 calc R B . H32B H 0.8756 0.2387 0.9331 0.11 Uiso 1 1 calc R . . H32C H 1.0188 0.222 0.9796 0.11 Uiso 1 1 calc R . . C33 C 1.0872(3) 0.31553(17) 0.88267(12) 0.0925(8) Uani 1 1 d . . . H33A H 1.1406 0.3245 0.8477 0.139 Uiso 1 1 calc R B . H33B H 1.145 0.3312 0.9225 0.139 Uiso 1 1 calc R . . H33C H 1.0018 0.3494 0.8762 0.139 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 C1 0.0688(15) 0.0553(15) 0.0769(18) 0.0056(12) 0.0131(13) 0.0041(11) C2 0.120(2) 0.0814(19) 0.089(2) 0.0211(16) 0.0032(18) 0.0224(16) C3 0.098(2) 0.093(2) 0.165(3) 0.032(2) 0.045(2) -0.0114(16) C4 0.100(2) 0.0897(19) 0.099(2) -0.0287(17) 0.0100(17) 0.0236(15) O1 0.0652(9) 0.0576(10) 0.0577(10) -0.0003(7) -0.0050(7) 0.0060(7) C5 0.0520(13) 0.0664(16) 0.0432(13) -0.0029(12) 0.0053(10) -0.0008(11) O2 0.0727(10) 0.0843(11) 0.0578(10) -0.0167(9) -0.0105(8) -0.0062(8) N1 0.0496(10) 0.0556(11) 0.0454(10) 0.0008(9) -0.0026(8) 0.0016(8) C6 0.0391(10) 0.0655(14) 0.0452(13) -0.0073(10) 0.0111(9) -0.0061(9) C7 0.0774(16) 0.0664(16) 0.0764(18) -0.0051(13) 0.0250(14) -0.0166(12) C8 0.0808(17) 0.0675(17) 0.092(2) 0.0174(15) 0.0265(15) 0.0111(13) C9 0.0548(12) 0.0783(16) 0.0544(14) 0.0171(13) 0.0061(11) 0.0031(11) N2 0.0300(8) 0.0800(12) 0.0446(11) -0.0047(9) 0.0068(8) 0.0002(8) C10 0.0320(11) 0.0622(13) 0.0496(13) -0.0085(10) 0.0059(10) -0.0024(9) O3 0.0289(7) 0.1085(12) 0.0615(10) -0.0039(9) 0.0076(6) -0.0048(7) N3 0.0302(8) 0.0879(13) 0.0499(11) 0.0020(9) 0.0046(8) -0.0004(8) C11 0.0415(11) 0.0740(15) 0.0507(14) -0.0026(11) -0.0004(10) -0.0043(10) C12 0.0723(15) 0.1064(19) 0.0529(15) -0.0008(13) 0.0082(12) 0.0057(13) C13 0.0851(17) 0.101(2) 0.088(2) 0.0070(16) 0.0071(15) 0.0350(15) C21 0.0679(14) 0.0461(14) 0.0729(17) -0.0061(12) 0.0124(12) 0.0026(11) C22 0.112(2) 0.0659(17) 0.091(2) -0.0206(15) -0.0096(17) -0.0086(14) C23 0.093(2) 0.096(2) 0.163(3) -0.045(2) 0.046(2) 0.0121(16) C24 0.125(2) 0.0726(18) 0.097(2) 0.0146(16) 0.0129(18) -0.0206(16) O21 0.0608(8) 0.0490(9) 0.0608(10) -0.0039(7) -0.0048(7) 0.0001(7) C25 0.0438(11) 0.0622(15) 0.0426(13) -0.0007(11) 0.0072(10) -0.0025(11) O22 0.0564(9) 0.0811(11) 0.0585(10) 0.0105(8) -0.0034(8) 0.0059(8) N21 0.0566(10) 0.0537(11) 0.0385(10) -0.0029(8) -0.0019(8) -0.0067(8) C26 0.0434(11) 0.0577(13) 0.0430(12) -0.0009(10) 0.0095(9) -0.0003(9) C27 0.0882(18) 0.0598(15) 0.0685(17) -0.0103(12) 0.0168(14) 0.0056(12) C28 0.083(4) 0.052(3) 0.078(4) -0.015(3) 0.018(3) -0.025(2) C29 0.0626(14) 0.0767(16) 0.0467(14) -0.0104(12) 0.0011(11) -0.0209(12) C47 0.0882(18) 0.0598(15) 0.0685(17) -0.0103(12) 0.0168(14) 0.0056(12) C48 0.081(4) 0.086(4) 0.064(4) -0.024(3) 0.018(3) -0.018(3) C49 0.0626(14) 0.0767(16) 0.0467(14) -0.0104(12) 0.0011(11) -0.0209(12) N22 0.0346(8) 0.0693(11) 0.0386(10) -0.0015(8) 0.0064(8) -0.0067(7) C30 0.0322(10) 0.0601(13) 0.0428(13) 0.0015(10) 0.0042(9) 0.0008(9) O23 0.0302(7) 0.1133(12) 0.0520(9) -0.0039(8) 0.0077(6) 0.0023(7) N23 0.0311(8) 0.0941(13) 0.0415(10) -0.0117(9) 0.0067(8) -0.0071(8) C31 0.0384(10) 0.0750(15) 0.0417(13) -0.0036(11) 0.0011(9) -0.0008(10) C32 0.0790(15) 0.0940(18) 0.0473(14) -0.0107(12) 0.0106(12) -0.0176(13) C33 0.1021(19) 0.099(2) 0.0720(18) 0.0035(15) -0.0027(15) -0.0388(16) _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 C1 O1 1.471(2) . ? C1 C4 1.503(3) . ? C1 C2 1.509(3) . ? C1 C3 1.517(3) . ? O1 C5 1.345(2) . ? C5 O2 1.212(2) . ? C5 N1 1.345(2) . ? N1 C6 1.457(2) . ? N1 C9 1.458(2) . ? C6 N2 1.443(2) . ? C6 C7 1.523(3) . ? C7 C8 1.506(3) . ? C8 C9 1.494(3) . ? N2 C10 1.347(2) . ? C10 O3 1.236(2) . ? C10 N3 1.353(2) . ? N3 C11 1.452(2) . ? C11 C12 1.510(3) . ? C11 C13 1.513(3) . ? C21 O21 1.466(2) . ? C21 C24 1.503(3) . ? C21 C22 1.506(3) . ? C21 C23 1.511(3) . ? O21 C25 1.345(2) . ? C25 O22 1.211(2) . ? C25 N21 1.353(2) . ? N21 C29 1.459(2) . ? N21 C26 1.459(2) . ? C26 N22 1.449(2) . ? C26 C27 1.523(3) . ? C27 C28 1.453(5) . ? C28 C29 1.503(5) . ? N22 C30 1.346(2) . ? C30 O23 1.2430(19) . ? C30 N23 1.347(2) . ? N23 C31 1.451(2) . ? C31 C33 1.502(3) . ? C31 C32 1.509(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 O1 C1 C4 110.11(19) . . ? O1 C1 C2 101.54(18) . . ? C4 C1 C2 111.5(2) . . ? O1 C1 C3 109.53(18) . . ? C4 C1 C3 111.5(2) . . ? C2 C1 C3 112.2(2) . . ? C5 O1 C1 121.12(17) . . ? O2 C5 O1 125.8(2) . . ? O2 C5 N1 123.4(2) . . ? O1 C5 N1 110.83(18) . . ? C5 N1 C6 126.17(17) . . ? C5 N1 C9 120.63(18) . . ? C6 N1 C9 112.81(17) . . ? N2 C6 N1 111.13(14) . . ? N2 C6 C7 114.26(17) . . ? N1 C6 C7 101.73(16) . . ? C8 C7 C6 104.03(17) . . ? C9 C8 C7 103.30(18) . . ? N1 C9 C8 103.20(18) . . ? C10 N2 C6 122.37(15) . . ? O3 C10 N2 122.47(18) . . ? O3 C10 N3 122.06(19) . . ? N2 C10 N3 115.46(16) . . ? C10 N3 C11 123.42(16) . . ? N3 C11 C12 109.05(16) . . ? N3 C11 C13 112.14(18) . . ? C12 C11 C13 111.67(19) . . ? O21 C21 C24 110.29(18) . . ? O21 C21 C22 102.41(17) . . ? C24 C21 C22 110.3(2) . . ? O21 C21 C23 109.40(18) . . ? C24 C21 C23 112.2(2) . . ? C22 C21 C23 111.8(2) . . ? C25 O21 C21 121.31(16) . . ? O22 C25 O21 125.7(2) . . ? O22 C25 N21 123.65(19) . . ? O21 C25 N21 110.66(18) . . ? C25 N21 C29 120.93(17) . . ? C25 N21 C26 125.96(17) . . ? C29 N21 C26 112.75(17) . . ? N22 C26 N21 110.99(14) . . ? N22 C26 C27 113.84(17) . . ? N21 C26 C27 102.44(16) . . ? C28 C27 C26 103.7(2) . . ? C27 C28 C29 106.2(3) . . ? N21 C29 C28 101.0(2) . . ? C30 N22 C26 122.79(15) . . ? O23 C30 N22 122.28(17) . . ? O23 C30 N23 122.15(18) . . ? N22 C30 N23 115.56(15) . . ? C30 N23 C31 123.11(15) . . ? N23 C31 C33 111.93(18) . . ? N23 C31 C32 108.91(15) . . ? C33 C31 C32 111.56(19) . . ? 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 C4 C1 O1 C5 65.2(2) . . . . ? C2 C1 O1 C5 -176.47(17) . . . . ? C3 C1 O1 C5 -57.7(3) . . . . ? C1 O1 C5 O2 -6.8(3) . . . . ? C1 O1 C5 N1 173.10(16) . . . . ? O2 C5 N1 C6 -176.59(18) . . . . ? O1 C5 N1 C6 3.5(3) . . . . ? O2 C5 N1 C9 -4.3(3) . . . . ? O1 C5 N1 C9 175.81(15) . . . . ? C5 N1 C6 N2 -76.3(2) . . . . ? C9 N1 C6 N2 110.89(18) . . . . ? C5 N1 C6 C7 161.66(18) . . . . ? C9 N1 C6 C7 -11.1(2) . . . . ? N2 C6 C7 C8 -89.2(2) . . . . ? N1 C6 C7 C8 30.6(2) . . . . ? C6 C7 C8 C9 -39.3(2) . . . . ? C5 N1 C9 C8 173.89(17) . . . . ? C6 N1 C9 C8 -12.9(2) . . . . ? C7 C8 C9 N1 31.7(2) . . . . ? N1 C6 N2 C10 136.97(18) . . . . ? C7 C6 N2 C10 -108.6(2) . . . . ? C6 N2 C10 O3 7.6(3) . . . . ? C6 N2 C10 N3 -173.41(16) . . . . ? O3 C10 N3 C11 -0.9(3) . . . . ? N2 C10 N3 C11 -179.86(17) . . . . ? C10 N3 C11 C12 163.49(19) . . . . ? C10 N3 C11 C13 -72.3(2) . . . . ? C24 C21 O21 C25 -64.1(2) . . . . ? C22 C21 O21 C25 178.51(18) . . . . ? C23 C21 O21 C25 59.7(3) . . . . ? C21 O21 C25 O22 7.9(3) . . . . ? C21 O21 C25 N21 -172.62(15) . . . . ? O22 C25 N21 C29 7.4(3) . . . . ? O21 C25 N21 C29 -172.09(15) . . . . ? O22 C25 N21 C26 179.93(17) . . . . ? O21 C25 N21 C26 0.5(3) . . . . ? C25 N21 C26 N22 73.1(2) . . . . ? C29 N21 C26 N22 -113.86(17) . . . . ? C25 N21 C26 C27 -165.08(18) . . . . ? C29 N21 C26 C27 8.0(2) . . . . ? N22 C26 C27 C28 92.0(4) . . . . ? N21 C26 C27 C28 -27.9(4) . . . . ? C26 C27 C28 C29 38.2(5) . . . . ? C25 N21 C29 C28 -172.3(3) . . . . ? C26 N21 C29 C28 14.2(4) . . . . ? C27 C28 C29 N21 -32.3(5) . . . . ? N21 C26 N22 C30 -137.45(18) . . . . ? C27 C26 N22 C30 107.6(2) . . . . ? C26 N22 C30 O23 -8.4(3) . . . . ? C26 N22 C30 N23 172.55(16) . . . . ? O23 C30 N23 C31 7.0(3) . . . . ? N22 C30 N23 C31 -173.97(17) . . . . ? C30 N23 C31 C33 74.5(2) . . . . ? C30 N23 C31 C32 -161.72(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O23 0.86 2.12 2.9340(19) 157.3 1_455 N3 H3 O23 0.86 2.28 3.057(2) 150.2 1_455 N22 H22 O3 0.86 2.21 2.9964(19) 151.4 . N23 H23 O3 0.86 2.17 2.9674(19) 153.8 . data_shelxl _database_code_depnum_ccdc_archive 'CCDC 668135' _audit_creation_date 2007-09-11T15:24:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H25 N3 O3' _chemical_formula_sum 'C16 H25 N3 O3' _chemical_formula_weight 307.39 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 20.565(5) _cell_length_b 5.2230(10) _cell_length_c 17.230(4) _cell_angle_alpha 90 _cell_angle_beta 105.921(8) _cell_angle_gamma 90 _cell_volume 1779.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 23.23 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0579 _diffrn_reflns_number 1410 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 23.23 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 1410 _reflns_number_gt 1117 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1526P)^2^+1.2396P] 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_number_reflns 1410 _refine_ls_number_parameters 208 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0856 _refine_ls_wR_factor_ref 0.2465 _refine_ls_wR_factor_gt 0.2327 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.335 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.051 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.6455(3) 0.2332(15) 0.3530(4) 0.0685(19) Uani 1 1 d . . . C2 C 0.7060(4) 0.3796(19) 0.3988(5) 0.095(3) Uani 1 1 d . . . H2A H 0.7401 0.2626 0.4276 0.142 Uiso 1 1 calc R . . H2B H 0.6935 0.4921 0.4364 0.142 Uiso 1 1 calc R . . H2C H 0.7233 0.4785 0.3619 0.142 Uiso 1 1 calc R . . C3 C 0.5884(4) 0.3957(18) 0.3058(6) 0.099(3) Uani 1 1 d . . . H3A H 0.5514 0.2881 0.2784 0.149 Uiso 1 1 calc R . . H3B H 0.6033 0.4947 0.2669 0.149 Uiso 1 1 calc R . . H3C H 0.574 0.5087 0.3418 0.149 Uiso 1 1 calc R . . C4 C 0.6218(5) 0.0544(19) 0.4106(5) 0.109(3) Uani 1 1 d . . . H4A H 0.659 -0.0494 0.4398 0.164 Uiso 1 1 calc R . . H4B H 0.5862 -0.0538 0.38 0.164 Uiso 1 1 calc R . . H4C H 0.6054 0.1548 0.4479 0.164 Uiso 1 1 calc R . . O1 O 0.6628(2) 0.0470(9) 0.2973(3) 0.0675(13) Uani 1 1 d . . . C5 C 0.6910(3) 0.1248(14) 0.2398(4) 0.0611(18) Uani 1 1 d . . . O2 O 0.7017(3) 0.3447(11) 0.2255(3) 0.0813(16) Uani 1 1 d . . . N1 N 0.7055(3) -0.0775(13) 0.1995(3) 0.0665(16) Uani 1 1 d . B . H1 H 0.6886 -0.2238 0.2061 0.08 Uiso 1 1 calc R . . C6 C 0.7486(3) -0.0614(17) 0.1451(4) 0.073(2) Uani 1 1 d D . . H6 H 0.7572 0.1217 0.1404 0.088 Uiso 1 1 calc R A 1 C7 C 0.8180(4) -0.1808(19) 0.1855(5) 0.088(3) Uani 1 1 d . B . H7A H 0.8116 -0.3556 0.201 0.105 Uiso 1 1 calc R . . H7B H 0.8445 -0.1858 0.1469 0.105 Uiso 1 1 calc R . . C8 C 0.8562(3) -0.0341(16) 0.2589(4) 0.072(2) Uani 1 1 d . . . C9 C 0.8948(4) 0.1714(19) 0.2493(5) 0.081(2) Uani 1 1 d . B . H9 H 0.897 0.2126 0.1976 0.098 Uiso 1 1 calc R . . C10 C 0.9299(5) 0.317(2) 0.3121(7) 0.111(3) Uani 1 1 d . . . H10 H 0.9551 0.4562 0.3031 0.133 Uiso 1 1 calc R B . C11 C 0.9279(5) 0.260(3) 0.3870(7) 0.117(4) Uani 1 1 d . B . H11 H 0.9521 0.36 0.4298 0.14 Uiso 1 1 calc R . . C12 C 0.8912(5) 0.057(3) 0.4024(6) 0.116(4) Uani 1 1 d . . . H12 H 0.89 0.0182 0.4547 0.139 Uiso 1 1 calc R B . C13 C 0.8539(4) -0.097(2) 0.3339(6) 0.105(3) Uani 1 1 d . B . H13 H 0.8287 -0.2378 0.3419 0.126 Uiso 1 1 calc R . . C14 C 0.7152(10) -0.154(4) 0.0582(9) 0.072(5) Uani 0.510(8) 1 d PD B 1 H14A H 0.7469 -0.1335 0.026 0.086 Uiso 0.510(8) 1 calc PR B 1 H14B H 0.7043 -0.334 0.0591 0.086 Uiso 0.510(8) 1 calc PR B 1 N2 N 0.6537(8) -0.010(3) 0.0210(11) 0.078(3) Uani 0.510(8) 1 d PD B 1 H2 H 0.6497 0.1501 0.0306 0.093 Uiso 0.510(8) 1 calc PR B 1 C15 C 0.6037(9) -0.144(4) -0.0296(13) 0.097(8) Uani 0.510(8) 1 d PD B 1 O3 O 0.5999(17) -0.376(4) -0.032(2) 0.146(8) Uani 0.510(8) 1 d PD B 1 N3 N 0.5515(7) 0.019(3) -0.0677(9) 0.096(3) Uiso 0.510(8) 1 d PD B 1 H3 H 0.5566 0.1815 -0.0614 0.116 Uiso 0.510(8) 1 calc PR B 1 C16 C 0.4886(8) -0.083(4) -0.1178(11) 0.102(4) Uiso 0.510(8) 1 d PD B 1 H16A H 0.4592 0.0563 -0.1413 0.153 Uiso 0.510(8) 1 calc PR B 1 H16B H 0.4674 -0.1855 -0.0855 0.153 Uiso 0.510(8) 1 calc PR B 1 H16C H 0.4975 -0.1857 -0.1599 0.153 Uiso 0.510(8) 1 calc PR B 1 C34 C 0.7178(11) -0.252(4) 0.0773(10) 0.072(5) Uani 0.490(8) 1 d PD B 2 H34A H 0.7495 -0.2818 0.0455 0.086 Uiso 0.490(8) 1 calc PR B 2 H34B H 0.7099 -0.4144 0.1005 0.086 Uiso 0.490(8) 1 calc PR B 2 N22 N 0.6546(8) -0.156(3) 0.0253(11) 0.078(3) Uani 0.490(8) 1 d PD B 2 H22 H 0.6473 0.0062 0.0241 0.093 Uiso 0.490(8) 1 calc PR B 2 C35 C 0.6059(10) -0.312(4) -0.0221(14) 0.097(8) Uani 0.490(8) 1 d PD B 2 O23 O 0.6100(16) -0.546(4) -0.025(2) 0.146(8) Uani 0.490(8) 1 d PD B 2 N23 N 0.5506(8) -0.163(4) -0.0632(9) 0.096(3) Uiso 0.490(8) 1 d PD B 2 H23 H 0.5506 0.0004 -0.0581 0.116 Uiso 0.490(8) 1 calc PR B 2 C36 C 0.4941(9) -0.296(4) -0.1140(11) 0.102(4) Uiso 0.490(8) 1 d PD B 2 H36A H 0.4575 -0.1779 -0.134 0.153 Uiso 0.490(8) 1 calc PR B 2 H36B H 0.4799 -0.4284 -0.0836 0.153 Uiso 0.490(8) 1 calc PR B 2 H36C H 0.5068 -0.3708 -0.1586 0.153 Uiso 0.490(8) 1 calc PR B 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 C1 0.073(4) 0.051(4) 0.088(5) -0.009(4) 0.033(4) 0.000(4) C2 0.104(6) 0.080(5) 0.094(5) -0.018(5) 0.016(5) -0.005(5) C3 0.089(6) 0.070(5) 0.139(7) -0.007(5) 0.030(5) 0.013(5) C4 0.165(9) 0.077(5) 0.113(7) -0.022(5) 0.085(6) -0.021(6) O1 0.082(3) 0.048(2) 0.082(3) -0.002(2) 0.039(3) -0.004(2) C5 0.062(4) 0.048(4) 0.070(4) 0.004(3) 0.014(3) -0.009(3) O2 0.103(4) 0.060(3) 0.091(4) 0.006(3) 0.045(3) -0.009(3) N1 0.066(3) 0.065(4) 0.076(3) -0.008(3) 0.033(3) -0.009(3) C6 0.067(4) 0.087(5) 0.071(4) -0.008(4) 0.028(3) -0.015(4) C7 0.061(4) 0.103(6) 0.105(6) -0.014(5) 0.035(4) -0.008(4) C8 0.060(4) 0.081(5) 0.078(5) 0.005(4) 0.027(4) 0.009(4) C9 0.065(4) 0.097(6) 0.084(5) -0.001(5) 0.021(4) 0.000(5) C10 0.075(6) 0.122(8) 0.124(8) 0.011(7) 0.010(6) -0.007(6) C11 0.090(7) 0.145(10) 0.101(8) -0.020(7) 0.001(5) 0.003(7) C12 0.118(8) 0.154(11) 0.073(5) 0.003(7) 0.022(6) 0.009(8) C13 0.094(6) 0.118(8) 0.110(7) 0.031(7) 0.043(5) 0.015(6) C14 0.078(6) 0.095(14) 0.050(7) 0.028(8) 0.030(6) 0.001(9) N2 0.078(5) 0.075(10) 0.076(4) -0.001(10) 0.014(4) 0.005(10) C15 0.070(8) 0.17(3) 0.054(7) -0.003(15) 0.021(6) -0.039(16) O3 0.116(11) 0.19(2) 0.137(10) -0.10(2) 0.037(8) -0.06(2) C34 0.078(6) 0.095(14) 0.050(7) 0.028(8) 0.030(6) 0.001(9) N22 0.078(5) 0.075(10) 0.076(4) -0.001(10) 0.014(4) 0.005(10) C35 0.070(8) 0.17(3) 0.054(7) -0.003(15) 0.021(6) -0.039(16) O23 0.116(11) 0.19(2) 0.137(10) -0.10(2) 0.037(8) -0.06(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.477(8) . ? C1 C2 1.489(10) . ? C1 C3 1.495(11) . ? C1 C4 1.536(11) . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? O1 C5 1.343(8) . ? C5 O2 1.207(8) . ? C5 N1 1.342(9) . ? N1 C6 1.458(8) . ? N1 H1 0.86 . ? C6 C34 1.535(17) . ? C6 C7 1.538(11) . ? C6 C14 1.544(16) . ? C6 H6 0.98 . ? C7 C8 1.503(11) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C13 1.348(11) . ? C8 C9 1.371(12) . ? C9 C10 1.358(13) . ? C9 H9 0.93 . ? C10 C11 1.337(14) . ? C10 H10 0.93 . ? C11 C12 1.368(18) . ? C11 H11 0.93 . ? C12 C13 1.460(15) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 N2 1.459(17) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? N2 C15 1.348(18) . ? N2 H2 0.86 . ? C15 O3 1.216(10) . ? C15 N3 1.385(18) . ? N3 C16 1.444(16) . ? N3 H3 0.86 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C34 N22 1.452(17) . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? N22 C35 1.373(18) . ? N22 H22 0.86 . ? C35 O23 1.228(10) . ? C35 N23 1.399(18) . ? N23 C36 1.428(16) . ? N23 H23 0.86 . ? C36 H36A 0.96 . ? C36 H36B 0.96 . ? C36 H36C 0.96 . ? 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 O1 C1 C2 111.5(5) . . ? O1 C1 C3 108.3(6) . . ? C2 C1 C3 114.4(7) . . ? O1 C1 C4 101.3(6) . . ? C2 C1 C4 109.7(7) . . ? C3 C1 C4 110.9(7) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 O1 C1 120.7(5) . . ? O2 C5 N1 124.4(7) . . ? O2 C5 O1 125.3(7) . . ? N1 C5 O1 110.2(6) . . ? C5 N1 C6 123.2(6) . . ? C5 N1 H1 118.4 . . ? C6 N1 H1 118.4 . . ? N1 C6 C34 104.8(10) . . ? N1 C6 C7 109.8(6) . . ? C34 C6 C7 102.6(10) . . ? N1 C6 C14 114.8(9) . . ? C34 C6 C14 22.7(8) . . ? C7 C6 C14 115.0(9) . . ? N1 C6 H6 105.4 . . ? C34 C6 H6 128.1 . . ? C7 C6 H6 105.4 . . ? C14 C6 H6 105.4 . . ? C8 C7 C6 112.3(7) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C13 C8 C9 118.8(8) . . ? C13 C8 C7 122.2(8) . . ? C9 C8 C7 119.0(7) . . ? C10 C9 C8 122.8(8) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C11 C10 C9 119.5(11) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 121.7(11) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C13 117.8(9) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? C8 C13 C12 119.4(10) . . ? C8 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? N2 C14 C6 111.5(15) . . ? N2 C14 H14A 109.3 . . ? C6 C14 H14A 109.3 . . ? N2 C14 H14B 109.3 . . ? C6 C14 H14B 109.3 . . ? H14A C14 H14B 108 . . ? C15 N2 C14 115.6(15) . . ? C15 N2 H2 122.2 . . ? C14 N2 H2 122.2 . . ? O3 C15 N2 125(2) . . ? O3 C15 N3 124(3) . . ? N2 C15 N3 110.0(16) . . ? C15 N3 C16 120.6(16) . . ? C15 N3 H3 119.7 . . ? C16 N3 H3 119.7 . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N22 C34 C6 110.9(15) . . ? N22 C34 H34A 109.5 . . ? C6 C34 H34A 109.5 . . ? N22 C34 H34B 109.5 . . ? C6 C34 H34B 109.5 . . ? H34A C34 H34B 108 . . ? C35 N22 C34 123.0(15) . . ? C35 N22 H22 118.5 . . ? C34 N22 H22 118.5 . . ? O23 C35 N22 125(2) . . ? O23 C35 N23 126(2) . . ? N22 C35 N23 109.3(17) . . ? C35 N23 C36 116.9(17) . . ? C35 N23 H23 121.5 . . ? C36 N23 H23 121.5 . . ? N23 C36 H36A 109.5 . . ? N23 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N23 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 O1 C5 -58.4(8) . . . . ? C3 C1 O1 C5 68.4(7) . . . . ? C4 C1 O1 C5 -175.0(6) . . . . ? C1 O1 C5 O2 -3.7(10) . . . . ? C1 O1 C5 N1 176.8(6) . . . . ? O2 C5 N1 C6 13.4(10) . . . . ? O1 C5 N1 C6 -167.0(5) . . . . ? C5 N1 C6 C34 -144.9(9) . . . . ? C5 N1 C6 C7 105.5(8) . . . . ? C5 N1 C6 C14 -123.2(10) . . . . ? N1 C6 C7 C8 -64.9(9) . . . . ? C34 C6 C7 C8 -175.9(9) . . . . ? C14 C6 C7 C8 163.9(9) . . . . ? C6 C7 C8 C13 94.2(10) . . . . ? C6 C7 C8 C9 -85.7(8) . . . . ? C13 C8 C9 C10 -1.2(13) . . . . ? C7 C8 C9 C10 178.7(8) . . . . ? C8 C9 C10 C11 0.7(15) . . . . ? C9 C10 C11 C12 -0.1(17) . . . . ? C10 C11 C12 C13 0.1(17) . . . . ? C9 C8 C13 C12 1.1(13) . . . . ? C7 C8 C13 C12 -178.7(8) . . . . ? C11 C12 C13 C8 -0.6(15) . . . . ? N1 C6 C14 N2 58.0(15) . . . . ? C34 C6 C14 N2 126(5) . . . . ? C7 C6 C14 N2 -173.2(11) . . . . ? C6 C14 N2 C15 -145.1(18) . . . . ? C14 N2 C15 O3 17(4) . . . . ? C14 N2 C15 N3 -173.3(16) . . . . ? O3 C15 N3 C16 -3(4) . . . . ? N2 C15 N3 C16 -172.9(18) . . . . ? N1 C6 C34 N22 72.3(15) . . . . ? C7 C6 C34 N22 -173.0(13) . . . . ? C14 C6 C34 N22 -47(3) . . . . ? C6 C34 N22 C35 -158(2) . . . . ? C34 N22 C35 O23 1(5) . . . . ? C34 N22 C35 N23 178.5(19) . . . . ? O23 C35 N23 C36 -1(4) . . . . ? N22 C35 N23 C36 -178.5(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.86 2.28 3.055(8) 149.3 1_545 N2 H2 O3 0.86 2.78 3.53(3) 146.4 1_565 N3 H3 O3 0.86 2.48 3.32(2) 166.5 1_565 N22 H22 O23 0.86 2.53 3.36(3) 162.3 1_565 N23 H23 O23 0.86 2.65 3.45(3) 153.8 1_565 data_prooxgly _database_code_depnum_ccdc_archive 'CCDC 668455' _audit_creation_date 2007-04-24T15:41:04-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H29 N3 O3' _chemical_formula_sum 'C14 H29 N3 O3' _chemical_formula_weight 287.4 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.169(6) _cell_length_b 9.397(3) _cell_length_c 16.467(2) _cell_angle_alpha 90 _cell_angle_beta 103.86(3) _cell_angle_gamma 90 _cell_volume 1828.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.8 _cell_measurement_theta_max 27.4 _cell_measurement_wavelength 1.54184 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.593 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.073171 _diffrn_orient_matrix_ub_12 -0.032558 _diffrn_orient_matrix_ub_13 0.011298 _diffrn_orient_matrix_ub_21 0.031394 _diffrn_orient_matrix_ub_22 0.015832 _diffrn_orient_matrix_ub_23 0.061225 _diffrn_orient_matrix_ub_31 -0.028721 _diffrn_orient_matrix_ub_32 0.100065 _diffrn_orient_matrix_ub_33 -0.006009 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 6 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -1 1 3 1 1 _diffrn_reflns_av_R_equivalents 0.0988 _diffrn_reflns_av_unetI/netI 0.0264 _diffrn_reflns_number 3249 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 64.94 _diffrn_reflns_theta_full 64.94 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3097 _reflns_number_gt 2405 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1299P)^2^+0.3600P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0048(9) _refine_ls_number_reflns 3097 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.2002 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.32 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 1.1905(2) 0.0822(3) 0.52022(15) 0.0680(7) Uani 1 1 d . . . C2 C 1.1791(3) -0.0250(4) 0.45015(18) 0.0980(11) Uani 1 1 d . . . H2A H 1.2281 -0.1044 0.4691 0.147 Uiso 1 1 calc R . . H2B H 1.1998 0.0189 0.4033 0.147 Uiso 1 1 calc R . . H2C H 1.1021 -0.0574 0.4336 0.147 Uiso 1 1 calc R . . C3 C 1.3137(3) 0.1221(4) 0.5556(2) 0.0997(11) Uani 1 1 d . . . H3A H 1.3575 0.0374 0.5719 0.15 Uiso 1 1 calc R . . H3B H 1.3195 0.1825 0.6035 0.15 Uiso 1 1 calc R . . H3C H 1.3418 0.1717 0.5138 0.15 Uiso 1 1 calc R . . C4 C 1.1146(3) 0.2086(4) 0.4919(2) 0.0924(10) Uani 1 1 d . . . H4A H 1.1229 0.2756 0.5369 0.139 Uiso 1 1 calc R . . H4B H 1.0373 0.1775 0.4753 0.139 Uiso 1 1 calc R . . H4C H 1.1353 0.2533 0.4452 0.139 Uiso 1 1 calc R . . O1 O 1.14994(14) 0.00003(17) 0.58342(9) 0.0593(5) Uani 1 1 d . . . C5 C 1.14822(19) 0.0558(2) 0.65840(13) 0.0505(5) Uani 1 1 d . . . O2 O 1.16579(18) 0.18078(17) 0.67697(11) 0.0745(6) Uani 1 1 d . . . N1 N 1.12367(16) -0.04304(18) 0.70806(10) 0.0480(5) Uani 1 1 d . . . H1 H 1.1128 -0.1286 0.6892 0.058 Uiso 1 1 calc R . . C6 C 1.11382(17) -0.0152(2) 0.79342(12) 0.0456(5) Uani 1 1 d . . . H6 H 1.1231 0.0871 0.8043 0.055 Uiso 1 1 calc R . . C7 C 1.20530(18) -0.0936(3) 0.85645(13) 0.0536(6) Uani 1 1 d . . . H7A H 1.1938 -0.1951 0.8474 0.064 Uiso 1 1 calc R . . H7B H 1.1963 -0.0725 0.9122 0.064 Uiso 1 1 calc R . . C8 C 1.3263(2) -0.0580(3) 0.85324(15) 0.0626(7) Uani 1 1 d . . . H8 H 1.3336 -0.0754 0.7961 0.075 Uiso 1 1 calc R . . C9 C 1.4092(2) -0.1555(4) 0.91165(19) 0.0929(10) Uani 1 1 d . . . H9A H 1.3902 -0.2529 0.8972 0.139 Uiso 1 1 calc R . . H9B H 1.405 -0.1386 0.9683 0.139 Uiso 1 1 calc R . . H9C H 1.4847 -0.1364 0.9063 0.139 Uiso 1 1 calc R . . C10 C 1.3555(3) 0.0964(4) 0.8740(2) 0.0930(10) Uani 1 1 d . . . H10A H 1.432 0.1142 0.8708 0.139 Uiso 1 1 calc R . . H10B H 1.348 0.1165 0.9296 0.139 Uiso 1 1 calc R . . H10C H 1.305 0.1564 0.8348 0.139 Uiso 1 1 calc R . . N2 N 1.00316(15) -0.05731(19) 0.80310(12) 0.0522(5) Uani 1 1 d . . . H2 H 0.9921 -0.1435 0.8169 0.063 Uiso 1 1 calc R . . C11 C 0.91632(18) 0.0379(2) 0.79060(12) 0.0468(5) Uani 1 1 d . . . O3 O 0.93143(14) 0.16597(16) 0.78235(11) 0.0617(5) Uani 1 1 d . . . N3 N 0.81340(16) -0.0187(2) 0.78748(13) 0.0601(6) Uani 1 1 d . . . H3 H 0.8065 -0.1098 0.7873 0.072 Uiso 1 1 calc R . . C12 C 0.7145(2) 0.0682(3) 0.78448(18) 0.0672(7) Uani 1 1 d . . . H12 H 0.7189 0.1515 0.7496 0.081 Uiso 1 1 calc R . . C13 C 0.6091(3) -0.0152(4) 0.7431(2) 0.0983(11) Uani 1 1 d . . . H13A H 0.6143 -0.0451 0.6884 0.147 Uiso 1 1 calc R . . H13B H 0.5436 0.0439 0.7384 0.147 Uiso 1 1 calc R . . H13C H 0.6028 -0.0973 0.7764 0.147 Uiso 1 1 calc R . . C14 C 0.7107(3) 0.1206(5) 0.8709(3) 0.1174(14) Uani 1 1 d . . . H14A H 0.7788 0.1721 0.8949 0.176 Uiso 1 1 calc R . . H14B H 0.7043 0.0407 0.9058 0.176 Uiso 1 1 calc R . . H14C H 0.6465 0.1821 0.8666 0.176 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 C1 0.0741(16) 0.0849(18) 0.0466(13) 0.0111(12) 0.0178(11) -0.0194(14) C2 0.118(3) 0.131(3) 0.0528(16) -0.0132(18) 0.0366(17) -0.018(2) C3 0.0778(19) 0.143(3) 0.080(2) 0.011(2) 0.0215(16) -0.037(2) C4 0.113(2) 0.094(2) 0.0690(18) 0.0323(17) 0.0183(16) -0.0098(19) O1 0.0814(11) 0.0590(10) 0.0412(8) -0.0024(7) 0.0218(7) -0.0148(8) C5 0.0630(13) 0.0448(12) 0.0436(11) -0.0023(9) 0.0126(9) -0.0062(10) O2 0.1196(16) 0.0474(10) 0.0628(10) -0.0011(8) 0.0342(10) -0.0158(9) N1 0.0649(11) 0.0413(9) 0.0381(9) -0.0027(7) 0.0132(8) -0.0050(8) C6 0.0524(12) 0.0464(11) 0.0402(10) -0.0016(8) 0.0156(9) -0.0012(9) C7 0.0555(13) 0.0651(14) 0.0397(11) -0.0019(10) 0.0106(9) 0.0029(10) C8 0.0532(13) 0.0866(18) 0.0478(12) -0.0098(12) 0.0119(10) 0.0029(12) C9 0.0613(16) 0.131(3) 0.0777(19) -0.0028(19) 0.0004(14) 0.0218(18) C10 0.0645(17) 0.098(2) 0.112(3) -0.017(2) 0.0127(17) -0.0139(16) N2 0.0514(10) 0.0436(10) 0.0653(12) 0.0087(8) 0.0213(9) 0.0014(8) C11 0.0553(12) 0.0438(11) 0.0447(11) 0.0021(9) 0.0190(9) 0.0031(9) O3 0.0683(10) 0.0426(9) 0.0811(11) 0.0050(8) 0.0316(9) 0.0026(7) N3 0.0567(12) 0.0497(11) 0.0797(14) 0.0098(10) 0.0277(10) 0.0036(8) C12 0.0597(14) 0.0645(15) 0.0845(18) 0.0132(13) 0.0312(13) 0.0117(12) C13 0.0600(17) 0.118(3) 0.116(3) 0.007(2) 0.0186(17) 0.0036(17) C14 0.109(3) 0.134(3) 0.130(3) -0.041(3) 0.069(3) -0.006(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O1 1.473(3) . ? C1 C4 1.509(4) . ? C1 C2 1.513(4) . ? C1 C3 1.520(4) . ? O1 C5 1.346(3) . ? C5 O2 1.220(3) . ? C5 N1 1.318(3) . ? N1 C6 1.463(2) . ? C6 N2 1.448(3) . ? C6 C7 1.518(3) . ? C7 C8 1.523(3) . ? C8 C10 1.513(4) . ? C8 C9 1.523(4) . ? N2 C11 1.362(3) . ? C11 O3 1.230(2) . ? C11 N3 1.350(3) . ? N3 C12 1.446(3) . ? C12 C14 1.517(4) . ? C12 C13 1.518(4) . ? 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 O1 C1 C4 110.3(2) . . ? O1 C1 C2 101.8(2) . . ? C4 C1 C2 110.5(3) . . ? O1 C1 C3 109.0(2) . . ? C4 C1 C3 113.5(3) . . ? C2 C1 C3 111.0(3) . . ? C5 O1 C1 121.71(18) . . ? O2 C5 N1 125.1(2) . . ? O2 C5 O1 124.4(2) . . ? N1 C5 O1 110.53(18) . . ? C5 N1 C6 123.59(18) . . ? N2 C6 N1 110.44(17) . . ? N2 C6 C7 109.94(17) . . ? N1 C6 C7 110.78(17) . . ? C6 C7 C8 115.2(2) . . ? C10 C8 C9 110.5(2) . . ? C10 C8 C7 112.3(2) . . ? C9 C8 C7 110.2(2) . . ? C11 N2 C6 120.80(18) . . ? O3 C11 N3 122.9(2) . . ? O3 C11 N2 121.9(2) . . ? N3 C11 N2 115.18(19) . . ? C11 N3 C12 122.4(2) . . ? N3 C12 C14 111.3(3) . . ? N3 C12 C13 109.3(2) . . ? C14 C12 C13 112.1(3) . . ? 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 C4 C1 O1 C5 -64.1(3) . . . . ? C2 C1 O1 C5 178.5(2) . . . . ? C3 C1 O1 C5 61.1(3) . . . . ? C1 O1 C5 O2 9.4(4) . . . . ? C1 O1 C5 N1 -171.4(2) . . . . ? O2 C5 N1 C6 0.2(4) . . . . ? O1 C5 N1 C6 -179.08(17) . . . . ? C5 N1 C6 N2 122.8(2) . . . . ? C5 N1 C6 C7 -115.2(2) . . . . ? N2 C6 C7 C8 -179.60(19) . . . . ? N1 C6 C7 C8 58.1(3) . . . . ? C6 C7 C8 C10 63.1(3) . . . . ? C6 C7 C8 C9 -173.2(2) . . . . ? N1 C6 N2 C11 -92.3(2) . . . . ? C7 C6 N2 C11 145.14(19) . . . . ? C6 N2 C11 O3 -10.3(3) . . . . ? C6 N2 C11 N3 169.26(19) . . . . ? O3 C11 N3 C12 -7.8(4) . . . . ? N2 C11 N3 C12 172.6(2) . . . . ? C11 N3 C12 C14 -81.1(3) . . . . ? C11 N3 C12 C13 154.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 0.86 2.55 3.273(3) 141.8 2_746 N1 H1 O3 0.86 2.09 2.829(2) 144 2_746 N3 H3 O2 0.86 2.06 2.883(3) 160.2 2_746