# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_06oc35m _database_code_depnum_ccdc_archive 'CCDC 851795' #TrackingRef '06oc35m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N O' _chemical_formula_weight 203.28 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7923(14) _cell_length_b 8.0377(11) _cell_length_c 14.520(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.817(2) _cell_angle_gamma 90.00 _cell_volume 1140.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3238 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description lump _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.91119 _exptl_absorpt_correction_T_max 0.95849 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 8265 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 28.37 _reflns_number_total 2847 _reflns_number_gt 2148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 1990)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2000)' _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^)+(0.1230P)^2^+0.0237P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2847 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 C1 C 0.18436(14) 0.01767(16) 0.53640(10) 0.0450(3) Uani 1 1 d . . . C2 C 0.26075(18) -0.00699(19) 0.45111(12) 0.0590(4) Uani 1 1 d . . . H2A H 0.2290 -0.1085 0.4205 0.071 Uiso 1 1 calc R . . H2B H 0.3574 -0.0203 0.4688 0.071 Uiso 1 1 calc R . . C3 C 0.24250(17) 0.1365(2) 0.38415(10) 0.0555(4) Uani 1 1 d . . . H3A H 0.1487 0.1377 0.3580 0.067 Uiso 1 1 calc R . . H3B H 0.3019 0.1202 0.3341 0.067 Uiso 1 1 calc R . . C4 C 0.27516(14) 0.30369(17) 0.43006(8) 0.0422(3) Uani 1 1 d . . . H4A H 0.3695 0.3001 0.4571 0.051 Uiso 1 1 calc R . . C5 C 0.17960(12) 0.33256(15) 0.50807(8) 0.0373(3) Uani 1 1 d . . . H5A H 0.0855 0.3272 0.4807 0.045 Uiso 1 1 calc R . . C6 C 0.19708(16) 0.50112(17) 0.55546(11) 0.0534(4) Uani 1 1 d . . . H6A H 0.1868 0.5884 0.5094 0.064 Uiso 1 1 calc R . . H6B H 0.1257 0.5154 0.5980 0.064 Uiso 1 1 calc R . . C7 C 0.3353(2) 0.5182(2) 0.60767(13) 0.0660(5) Uani 1 1 d . . . H7A H 0.3414 0.6258 0.6380 0.079 Uiso 1 1 calc R . . H7B H 0.4069 0.5122 0.5647 0.079 Uiso 1 1 calc R . . C8 C 0.35623(18) 0.3813(2) 0.67926(11) 0.0624(5) Uani 1 1 d . . . H8A H 0.4493 0.3873 0.7064 0.075 Uiso 1 1 calc R . . H8B H 0.2952 0.4007 0.7281 0.075 Uiso 1 1 calc R . . C9 C 0.33097(14) 0.20955(19) 0.64115(9) 0.0454(4) Uani 1 1 d . . . H9A H 0.3795 0.2375 0.5863 0.054 Uiso 1 1 calc R . . C10 C 0.19619(12) 0.19049(15) 0.58174(8) 0.0360(3) Uani 1 1 d . . . C11 C 0.08372(14) 0.20698(17) 0.64413(9) 0.0445(3) Uani 1 1 d . . . C12 C 0.41494(17) 0.0831(2) 0.65948(12) 0.0651(5) Uani 1 1 d . . . C13 C 0.2645(2) 0.4433(3) 0.35896(12) 0.0686(5) Uani 1 1 d . . . H13A H 0.3259 0.4216 0.3116 0.103 Uiso 1 1 calc R . . H13B H 0.2883 0.5471 0.3885 0.103 Uiso 1 1 calc R . . H13C H 0.1724 0.4493 0.3320 0.103 Uiso 1 1 calc R . . N1 N -0.00169(15) 0.22598(19) 0.69218(10) 0.0647(4) Uani 1 1 d . . . O1 O 0.11637(13) -0.08993(13) 0.56842(9) 0.0667(4) Uani 1 1 d . . . H12A H 0.5021 0.1026 0.6969 0.080 Uiso 1 1 d . . . H12B H 0.3981 -0.0304 0.6329 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0436(7) 0.0352(7) 0.0562(8) 0.0005(6) 0.0023(6) 0.0014(5) C2 0.0647(10) 0.0447(8) 0.0690(10) -0.0170(7) 0.0149(8) -0.0004(6) C3 0.0566(9) 0.0665(10) 0.0439(7) -0.0136(7) 0.0071(6) -0.0018(7) C4 0.0396(7) 0.0493(8) 0.0380(6) 0.0033(5) 0.0054(5) 0.0003(5) C5 0.0352(6) 0.0375(7) 0.0394(6) 0.0034(5) 0.0035(5) 0.0025(5) C6 0.0651(10) 0.0359(7) 0.0606(9) -0.0002(6) 0.0155(7) 0.0030(6) C7 0.0771(11) 0.0511(9) 0.0706(11) -0.0170(8) 0.0106(9) -0.0207(8) C8 0.0597(10) 0.0753(11) 0.0512(8) -0.0155(8) -0.0040(7) -0.0120(8) C9 0.0411(7) 0.0604(9) 0.0348(6) 0.0040(6) 0.0040(5) -0.0010(6) C10 0.0350(6) 0.0350(6) 0.0386(6) 0.0019(5) 0.0060(5) 0.0016(4) C11 0.0429(7) 0.0448(7) 0.0463(7) 0.0071(5) 0.0074(6) 0.0019(5) C12 0.0504(9) 0.0828(12) 0.0611(9) 0.0123(8) -0.0037(7) 0.0155(8) C13 0.0774(12) 0.0760(12) 0.0544(9) 0.0229(8) 0.0192(8) 0.0084(9) N1 0.0619(9) 0.0717(9) 0.0637(8) 0.0087(7) 0.0269(7) 0.0062(6) O1 0.0742(8) 0.0397(6) 0.0877(8) 0.0051(5) 0.0167(6) -0.0107(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2035(17) . ? C1 C2 1.502(2) . ? C1 C10 1.5383(18) . ? C2 C3 1.512(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.524(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C13 1.524(2) . ? C4 C5 1.5341(17) . ? C4 H4A 0.9800 . ? C5 C6 1.5241(19) . ? C5 C10 1.5657(16) . ? C5 H5A 0.9800 . ? C6 C7 1.513(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.518(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.502(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C12 1.323(2) . ? C9 C10 1.5355(17) . ? C9 H9A 0.9800 . ? C10 C11 1.4779(17) . ? C11 N1 1.1346(18) . ? C12 H12A 0.9932 . ? C12 H12B 1.0002 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 O1 C1 C2 122.84(13) . . ? O1 C1 C10 120.76(13) . . ? C2 C1 C10 116.40(11) . . ? C1 C2 C3 112.68(12) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 112.27(11) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C13 C4 C3 110.49(13) . . ? C13 C4 C5 111.78(12) . . ? C3 C4 C5 109.61(11) . . ? C13 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C6 C5 C4 114.34(11) . . ? C6 C5 C10 109.66(10) . . ? C4 C5 C10 110.70(10) . . ? C6 C5 H5A 107.3 . . ? C4 C5 H5A 107.3 . . ? C10 C5 H5A 107.3 . . ? C7 C6 C5 112.13(12) . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 110.68(13) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C7 113.73(12) . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C12 C9 C8 123.17(14) . . ? C12 C9 C10 122.40(14) . . ? C8 C9 C10 114.39(12) . . ? C12 C9 H9A 90.7 . . ? C8 C9 H9A 90.7 . . ? C10 C9 H9A 90.7 . . ? C11 C10 C9 107.12(10) . . ? C11 C10 C1 107.78(10) . . ? C9 C10 C1 111.59(10) . . ? C11 C10 C5 107.80(10) . . ? C9 C10 C5 110.93(10) . . ? C1 C10 C5 111.39(10) . . ? N1 C11 C10 177.38(15) . . ? C9 C12 H12A 119.3 . . ? C9 C12 H12B 122.6 . . ? H12A C12 H12B 117.9 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.269 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.053 data_ap46m _database_code_depnum_ccdc_archive 'CCDC 851796' #TrackingRef 'ap46m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N5 O4' _chemical_formula_weight 369.38 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.1764(14) _cell_length_b 7.0909(7) _cell_length_c 19.046(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.154(3) _cell_angle_gamma 90.00 _cell_volume 1778.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1424 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 20.93 _exptl_crystal_description Columnar _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.52324 _exptl_absorpt_correction_T_max 0.90762 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 12845 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0917 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4419 _reflns_number_gt 2180 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4419 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1310 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 0.28527(13) 0.6528(3) 0.20332(9) 0.0708(5) Uani 1 1 d . . . O2 O 0.43779(13) 0.5464(3) 0.21813(10) 0.0840(6) Uani 1 1 d . . . O3 O 0.54149(14) -0.0384(3) 0.12585(13) 0.1088(8) Uani 1 1 d . . . O4 O 0.43506(15) -0.2108(3) 0.06641(12) 0.1049(8) Uani 1 1 d . . . N1 N 0.04747(12) 0.4007(2) 0.11775(8) 0.0401(4) Uani 1 1 d . . . N2 N 0.14281(12) 0.4416(3) 0.14597(8) 0.0455(5) Uani 1 1 d . . . H2A H 0.1535 0.5457 0.1682 0.055 Uiso 1 1 calc R . . N3 N -0.10539(14) 0.2203(3) -0.00606(11) 0.0625(6) Uani 1 1 d . . . N4 N 0.34984(15) 0.5278(3) 0.19628(10) 0.0558(5) Uani 1 1 d . . . N5 N 0.45622(16) -0.0716(3) 0.10150(13) 0.0736(7) Uani 1 1 d . . . C1 C -0.01563(19) 0.7037(3) 0.16508(14) 0.0689(8) Uani 1 1 d . . . H1A H 0.0551 0.7409 0.1697 0.083 Uiso 1 1 calc R . . H1B H -0.0400 0.6848 0.2120 0.083 Uiso 1 1 calc R . . C2 C -0.07582(19) 0.8630(3) 0.13002(14) 0.0701(8) Uani 1 1 d . . . H2B H -0.0776 0.9700 0.1617 0.084 Uiso 1 1 calc R . . H2C H -0.0424 0.9027 0.0880 0.084 Uiso 1 1 calc R . . C3 C -0.18303(17) 0.8015(3) 0.11071(13) 0.0604(7) Uani 1 1 d . . . H3A H -0.2196 0.9058 0.0887 0.072 Uiso 1 1 calc R . . H3B H -0.2174 0.7676 0.1531 0.072 Uiso 1 1 calc R . . C4 C -0.18459(15) 0.6346(3) 0.06101(11) 0.0438(5) Uani 1 1 d . . . H4A H -0.1475 0.6717 0.0196 0.053 Uiso 1 1 calc R . . C5 C -0.29208(16) 0.5781(3) 0.03548(12) 0.0554(6) Uani 1 1 d . . . H5A H -0.3269 0.6886 0.0166 0.066 Uiso 1 1 calc R . . H5B H -0.2873 0.4871 -0.0023 0.066 Uiso 1 1 calc R . . C6 C -0.35429(16) 0.4939(4) 0.09277(13) 0.0644(7) Uani 1 1 d . . . H6A H -0.4201 0.4552 0.0733 0.077 Uiso 1 1 calc R . . H6B H -0.3651 0.5879 0.1287 0.077 Uiso 1 1 calc R . . C7 C -0.29902(17) 0.3236(4) 0.12531(14) 0.0679(7) Uani 1 1 d . . . H7A H -0.3367 0.2783 0.1647 0.082 Uiso 1 1 calc R . . H7B H -0.2976 0.2232 0.0908 0.082 Uiso 1 1 calc R . . C8 C -0.19223(16) 0.3678(3) 0.15020(12) 0.0504(6) Uani 1 1 d . . . C9 C -0.12671(14) 0.4624(3) 0.09563(10) 0.0375(5) Uani 1 1 d . . . C10 C -0.02255(15) 0.5212(3) 0.12618(10) 0.0407(5) Uani 1 1 d . . . C11 C 0.21922(15) 0.3173(3) 0.13851(10) 0.0384(5) Uani 1 1 d . . . C12 C 0.19962(15) 0.1408(3) 0.10658(11) 0.0438(5) Uani 1 1 d . . . H12A H 0.1333 0.1093 0.0929 0.053 Uiso 1 1 calc R . . C13 C 0.27564(15) 0.0157(3) 0.09540(11) 0.0495(6) Uani 1 1 d . . . H13A H 0.2612 -0.0995 0.0739 0.059 Uiso 1 1 calc R . . C14 C 0.37477(16) 0.0607(3) 0.11620(12) 0.0499(6) Uani 1 1 d . . . C15 C 0.39750(15) 0.2268(3) 0.14928(11) 0.0486(6) Uani 1 1 d . . . H15A H 0.4640 0.2540 0.1640 0.058 Uiso 1 1 calc R . . C16 C 0.32024(15) 0.3546(3) 0.16075(10) 0.0409(5) Uani 1 1 d . . . C17 C -0.1562(2) 0.3215(4) 0.21316(13) 0.0810(9) Uani 1 1 d . . . H17A H -0.1973 0.2590 0.2442 0.097 Uiso 1 1 calc R . . H17C H -0.0895 0.3514 0.2266 0.097 Uiso 1 1 calc R . . C18 C -0.11199(14) 0.3232(3) 0.03934(11) 0.0403(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0662(12) 0.0587(12) 0.0866(13) -0.0221(10) -0.0093(9) 0.0021(10) O2 0.0623(12) 0.0765(14) 0.1104(15) -0.0169(12) -0.0352(10) -0.0111(10) O3 0.0425(11) 0.0901(16) 0.192(2) -0.0178(15) -0.0238(12) 0.0162(11) O4 0.0755(14) 0.0903(17) 0.147(2) -0.0485(15) -0.0232(13) 0.0341(12) N1 0.0365(10) 0.0430(11) 0.0405(10) -0.0011(8) -0.0024(7) 0.0057(8) N2 0.0420(10) 0.0419(11) 0.0518(11) -0.0093(9) -0.0080(8) 0.0045(9) N3 0.0504(12) 0.0675(15) 0.0696(14) -0.0267(12) 0.0013(10) 0.0036(10) N4 0.0542(13) 0.0574(14) 0.0548(13) -0.0016(11) -0.0117(10) -0.0046(11) N5 0.0488(14) 0.0646(16) 0.1064(19) -0.0012(15) -0.0121(12) 0.0152(12) C1 0.0686(17) 0.0623(18) 0.0750(18) -0.0275(15) -0.0079(13) 0.0174(14) C2 0.0679(17) 0.0482(16) 0.094(2) -0.0222(15) 0.0004(14) 0.0158(14) C3 0.0588(16) 0.0446(15) 0.0786(18) -0.0019(13) 0.0128(12) 0.0220(12) C4 0.0435(13) 0.0435(13) 0.0448(13) 0.0081(11) 0.0088(9) 0.0114(10) C5 0.0439(13) 0.0573(16) 0.0648(16) 0.0112(13) -0.0003(11) 0.0149(12) C6 0.0402(14) 0.0691(18) 0.0848(19) 0.0092(15) 0.0123(12) 0.0102(12) C7 0.0491(15) 0.0689(18) 0.0873(19) 0.0251(15) 0.0232(13) 0.0028(13) C8 0.0525(14) 0.0472(14) 0.0526(15) 0.0109(12) 0.0150(11) 0.0150(11) C9 0.0397(11) 0.0358(12) 0.0373(12) -0.0018(10) 0.0060(9) 0.0089(9) C10 0.0449(12) 0.0420(13) 0.0354(12) -0.0036(10) 0.0041(9) 0.0088(10) C11 0.0401(12) 0.0386(13) 0.0362(12) 0.0055(10) -0.0044(9) 0.0026(10) C12 0.0348(12) 0.0412(13) 0.0545(14) 0.0047(11) -0.0084(9) -0.0002(10) C13 0.0458(13) 0.0397(14) 0.0621(15) 0.0007(11) -0.0102(11) 0.0035(11) C14 0.0400(13) 0.0473(15) 0.0616(15) 0.0029(13) -0.0087(10) 0.0091(11) C15 0.0344(12) 0.0572(16) 0.0533(14) 0.0083(12) -0.0107(10) -0.0021(11) C16 0.0403(12) 0.0437(13) 0.0381(12) 0.0021(10) -0.0061(9) -0.0054(10) C17 0.084(2) 0.103(2) 0.0578(17) 0.0263(17) 0.0236(14) 0.0200(18) C18 0.0304(11) 0.0429(14) 0.0477(14) -0.0018(11) 0.0030(9) 0.0030(10) _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 N4 1.239(2) . ? O2 N4 1.224(2) . ? O3 N5 1.222(2) . ? O4 N5 1.218(3) . ? N1 C10 1.272(2) . ? N1 N2 1.379(2) . ? N2 C11 1.350(2) . ? N2 H2A 0.8600 . ? N3 C18 1.137(2) . ? N4 C16 1.449(3) . ? N5 C14 1.460(3) . ? C1 C10 1.492(3) . ? C1 C2 1.520(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.511(3) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 C4 1.515(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.533(3) . ? C4 C9 1.571(3) . ? C4 H4A 0.9800 . ? C5 C6 1.512(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.529(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.501(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C17 1.315(3) . ? C8 C9 1.531(3) . ? C9 C18 1.476(3) . ? C9 C10 1.528(3) . ? C11 C16 1.407(3) . ? C11 C12 1.411(3) . ? C12 C13 1.361(3) . ? C12 H12A 0.9300 . ? C13 C14 1.388(3) . ? C13 H13A 0.9300 . ? C14 C15 1.364(3) . ? C15 C16 1.386(3) . ? C15 H15A 0.9300 . ? C17 H17A 0.9300 . ? C17 H17C 0.9300 . ? 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 C10 N1 N2 117.64(17) . . ? C11 N2 N1 119.60(17) . . ? C11 N2 H2A 120.2 . . ? N1 N2 H2A 120.2 . . ? O2 N4 O1 122.1(2) . . ? O2 N4 C16 119.0(2) . . ? O1 N4 C16 118.89(17) . . ? O4 N5 O3 123.5(2) . . ? O4 N5 C14 118.1(2) . . ? O3 N5 C14 118.4(2) . . ? C10 C1 C2 113.90(19) . . ? C10 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? C10 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 111.1(2) . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2C 109.4 . . ? C1 C2 H2C 109.4 . . ? H2B C2 H2C 108.0 . . ? C2 C3 C4 111.61(18) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 113.13(18) . . ? C3 C4 C9 110.47(16) . . ? C5 C4 C9 110.98(18) . . ? C3 C4 H4A 107.3 . . ? C5 C4 H4A 107.3 . . ? C9 C4 H4A 107.3 . . ? C6 C5 C4 113.19(18) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 109.96(19) . . ? C5 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C8 C7 C6 112.9(2) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C17 C8 C7 122.6(2) . . ? C17 C8 C9 122.3(2) . . ? C7 C8 C9 115.03(19) . . ? C18 C9 C10 108.57(16) . . ? C18 C9 C8 107.03(17) . . ? C10 C9 C8 112.48(17) . . ? C18 C9 C4 106.85(16) . . ? C10 C9 C4 111.26(17) . . ? C8 C9 C4 110.38(16) . . ? N1 C10 C1 127.88(19) . . ? N1 C10 C9 114.45(18) . . ? C1 C10 C9 117.57(18) . . ? N2 C11 C16 123.15(19) . . ? N2 C11 C12 119.96(18) . . ? C16 C11 C12 116.89(19) . . ? C13 C12 C11 121.45(19) . . ? C13 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13A 120.1 . . ? C14 C13 H13A 120.1 . . ? C15 C14 C13 121.2(2) . . ? C15 C14 N5 119.5(2) . . ? C13 C14 N5 119.2(2) . . ? C14 C15 C16 119.18(19) . . ? C14 C15 H15A 120.4 . . ? C16 C15 H15A 120.4 . . ? C15 C16 C11 121.5(2) . . ? C15 C16 N4 116.20(18) . . ? C11 C16 N4 122.3(2) . . ? C8 C17 H17A 120.0 . . ? C8 C17 H17C 120.0 . . ? H17A C17 H17C 120.0 . . ? N3 C18 C9 176.0(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.185 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.047