# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1547 data_omc9901 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.29 _chemical_melting_point ? _chemical_compound_source ? 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.269(2) _cell_length_b 8.6418(12) _cell_length_c 12.173(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.16(2) _cell_angle_gamma 90.00 _cell_volume 639.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 5.02 _cell_measurement_theta_max 12.45 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method ? _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 6.91 _diffrn_reflns_number 2121 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 29.99 _reflns_number_total 1961 _reflns_number_observed 1674 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 74 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0781P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.29(161) _refine_ls_number_reflns 1887 _refine_ls_number_parameters 155 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_obs 0.0460 _refine_ls_wR_factor_all 0.1256 _refine_ls_wR_factor_obs 0.1166 _refine_ls_goodness_of_fit_all 1.053 _refine_ls_goodness_of_fit_obs 1.076 _refine_ls_restrained_S_all 1.064 _refine_ls_restrained_S_obs 1.075 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.6315(3) 0.8049(2) 0.09171(12) 0.0511(4) Uani 1 d . . C2 C 0.4454(3) 0.7459(3) 0.0108(2) 0.0479(4) Uani 1 d . . H2A H 0.3160(3) 0.8066(3) 0.0124(2) 0.057 Uiso 1 calc R . H2B H 0.4185(3) 0.6396(3) 0.0289(2) 0.057 Uiso 1 calc R . C3 C 0.4900(4) 0.7542(2) -0.1048(2) 0.0445(4) Uani 1 d . . H3A H 0.5161(4) 0.8620(2) -0.1230(2) 0.053 Uiso 1 calc R . C4 C 0.3202(5) 0.6820(3) -0.2027(2) 0.0579(5) Uani 1 d . . H4A H 0.2540(5) 0.5908(3) -0.1785(2) 0.070 Uiso 1 calc R . H4B H 0.2053(5) 0.7554(3) -0.2359(2) 0.070 Uiso 1 calc R . C5 C 0.4579(6) 0.6406(4) -0.2850(2) 0.0742(8) Uani 1 d . . H5A H 0.4853(6) 0.7312(4) -0.3265(2) 0.089 Uiso 1 calc R . H5B H 0.3847(6) 0.5628(4) -0.3386(2) 0.089 Uiso 1 calc R . C6 C 0.6723(5) 0.5776(4) -0.2104(2) 0.0628(6) Uani 1 d . . H6A H 0.6644(5) 0.4666(4) -0.2002(2) 0.075 Uiso 1 calc R . H6B H 0.7963(5) 0.6012(4) -0.2420(2) 0.075 Uiso 1 calc R . N7 N 0.6878(3) 0.6613(2) -0.10252(14) 0.0466(4) Uani 1 d . . C8 C 0.8409(3) 0.6320(2) -0.0088(2) 0.0422(4) Uani 1 d . . O8 O 0.9919(3) 0.5374(3) -0.0056(2) 0.0603(4) Uani 1 d . . C9 C 0.8284(3) 0.7199(2) 0.09919(14) 0.0396(3) Uani 1 d . . H9A H 0.9492(3) 0.7949(2) 0.11440(14) 0.048 Uiso 1 calc R . C10 C 0.8702(4) 0.6082(2) 0.2015(2) 0.0467(4) Uani 1 d . . H10A H 0.7593(4) 0.5259(2) 0.1849(2) 0.056 Uiso 1 calc R . O10 O 1.0821(4) 0.5388(3) 0.2191(2) 0.0780(7) Uani 1 d D . H10B H 1.1011(72) 0.5248(64) 0.1489(15) 0.108(16) Uiso 1 d D . C11 C 0.8513(3) 0.6898(2) 0.30882(11) 0.0486(4) Uani 1 d G . C12 C 0.6639(3) 0.6710(3) 0.34927(13) 0.0619(6) Uani 1 d G . H12A H 0.5485(3) 0.6099(3) 0.3096(2) 0.074 Uiso 1 calc R . C13 C 0.6490(3) 0.7435(3) 0.44904(14) 0.0816(10) Uani 1 d G . H13A H 0.5237(4) 0.7310(5) 0.4761(2) 0.098 Uiso 1 calc R . C14 C 0.8216(4) 0.8348(3) 0.50836(13) 0.0861(11) Uani 1 d G . H14A H 0.8116(5) 0.8834(4) 0.5751(2) 0.103 Uiso 1 calc R . C15 C 1.0090(4) 0.8536(3) 0.4679(2) 0.0839(11) Uani 1 d G . H15A H 1.1244(5) 0.9147(4) 0.5076(2) 0.101 Uiso 1 calc R . C16 C 1.0239(3) 0.7811(2) 0.36814(15) 0.0673(7) Uani 1 d G . H16A H 1.1492(3) 0.7937(4) 0.3411(2) 0.081 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0553(8) 0.0483(7) 0.0468(6) -0.0106(6) 0.0070(6) 0.0102(7) C2 0.0417(9) 0.0522(10) 0.0500(8) -0.0022(8) 0.0115(7) 0.0107(8) C3 0.0506(10) 0.0367(7) 0.0428(7) 0.0016(6) 0.0049(7) 0.0034(8) C4 0.0595(12) 0.0538(11) 0.0522(10) -0.0040(9) -0.0024(9) 0.0005(11) C5 0.093(2) 0.082(2) 0.0425(9) -0.0085(11) 0.0056(12) 0.001(2) C6 0.075(2) 0.0716(15) 0.0456(9) -0.0132(10) 0.0216(11) 0.0009(13) N7 0.0513(9) 0.0481(8) 0.0421(7) -0.0037(6) 0.0144(7) 0.0017(7) C8 0.0403(8) 0.0412(8) 0.0479(8) -0.0036(7) 0.0162(7) -0.0018(8) O8 0.0469(8) 0.0670(11) 0.0690(9) -0.0099(8) 0.0179(7) 0.0120(8) C9 0.0400(8) 0.0358(7) 0.0416(7) -0.0026(6) 0.0073(6) -0.0042(6) C10 0.0498(10) 0.0415(8) 0.0462(8) 0.0014(7) 0.0064(8) -0.0013(8) O10 0.0761(13) 0.087(2) 0.0652(11) 0.0068(11) 0.0063(10) 0.0360(13) C11 0.0507(11) 0.0494(9) 0.0416(8) 0.0038(7) 0.0033(8) -0.0043(9) C12 0.0569(12) 0.078(2) 0.0490(9) 0.0053(10) 0.0090(9) -0.0039(13) C13 0.078(2) 0.119(3) 0.0507(11) 0.009(2) 0.0207(12) 0.016(2) C14 0.111(3) 0.095(2) 0.0430(10) -0.0065(12) 0.0027(14) 0.020(2) C15 0.095(2) 0.086(2) 0.0581(13) -0.0159(14) -0.007(2) -0.014(2) C16 0.0622(14) 0.073(2) 0.0596(12) -0.0058(11) 0.0009(11) -0.0185(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.420(2) . ? O1 C2 1.424(3) . ? C2 C3 1.502(3) . ? C3 N7 1.472(3) . ? C3 C4 1.524(3) . ? C4 C5 1.516(4) . ? C5 C6 1.526(4) . ? C6 N7 1.481(3) . ? N7 C8 1.323(3) . ? C8 O8 1.244(3) . ? C8 C9 1.537(2) . ? C9 C10 1.547(3) . ? C10 O10 1.425(3) . ? C10 C11 1.514(2) . ? C11 C12 1.39 . ? C11 C16 1.39 . ? C12 C13 1.39 . ? C13 C14 1.39 . ? C14 C15 1.39 . ? C15 C16 1.39 . ? 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 C9 O1 C2 114.30(15) . . ? O1 C2 C3 108.8(2) . . ? N7 C3 C2 107.8(2) . . ? N7 C3 C4 102.5(2) . . ? C2 C3 C4 117.3(2) . . ? C5 C4 C3 102.2(2) . . ? C4 C5 C6 104.6(2) . . ? N7 C6 C5 102.2(2) . . ? C8 N7 C3 123.4(2) . . ? C8 N7 C6 123.2(2) . . ? C3 N7 C6 112.1(2) . . ? O8 C8 N7 122.6(2) . . ? O8 C8 C9 119.7(2) . . ? N7 C8 C9 117.7(2) . . ? O1 C9 C8 115.23(15) . . ? O1 C9 C10 110.4(2) . . ? C8 C9 C10 110.2(2) . . ? O10 C10 C11 109.5(2) . . ? O10 C10 C9 110.6(2) . . ? C11 C10 C9 111.7(2) . . ? C12 C11 C16 120.0 . . ? C12 C11 C10 120.17(14) . . ? C16 C11 C10 119.82(14) . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C15 C14 C13 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C11 120.0 . . ? _refine_diff_density_max 0.250 _refine_diff_density_min -0.121 _refine_diff_density_rms 0.037 data_omc9902 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H20 N2 O3' _chemical_formula_weight 336.38 _chemical_melting_point ? _chemical_compound_source ? 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 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.2710(10) _cell_length_b 10.9937(11) _cell_length_c 24.771(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1707.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 8.90 _cell_measurement_theta_max 21.94 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max .753 _exptl_crystal_size_mid .024 _exptl_crystal_size_min .005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method ? _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.719 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4/RA' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1675 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0909 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 63.98 _reflns_number_total 1675 _reflns_number_observed 1071 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 198 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.4103P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.29(103) _refine_ls_number_reflns 1477 _refine_ls_number_parameters 207 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_obs 0.0657 _refine_ls_wR_factor_all 0.2087 _refine_ls_wR_factor_obs 0.1511 _refine_ls_goodness_of_fit_all 1.049 _refine_ls_goodness_of_fit_obs 1.110 _refine_ls_restrained_S_all 1.187 _refine_ls_restrained_S_obs 1.109 _refine_ls_shift/esd_max 0.010 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.3477(9) -0.3194(5) -0.1445(2) 0.0313(12) Uani 1 d . . C2 C -0.1639(12) -0.3836(6) -0.1421(3) 0.037(2) Uani 1 d . . O2 O -0.0315(9) -0.3854(5) -0.1773(2) 0.0534(15) Uani 1 d . . C3 C -0.1296(12) -0.4591(6) -0.0914(3) 0.038(2) Uani 1 d . . H3A H -0.0344(12) -0.4138(6) -0.0674(3) 0.046 Uiso 1 calc R . C4 C -0.0315(14) -0.5834(7) -0.1016(3) 0.048(2) Uani 1 d . . H4A H 0.1211(14) -0.5778(7) -0.1075(3) 0.057 Uiso 1 calc R . H4B H -0.0975(14) -0.6237(7) -0.1321(3) 0.057 Uiso 1 calc R . C5 C -0.0821(15) -0.6484(7) -0.0488(3) 0.052(2) Uani 1 d . . H5A H 0.0238(15) -0.6289(7) -0.0216(3) 0.062 Uiso 1 calc R . H5B H -0.0836(15) -0.7358(7) -0.0541(3) 0.062 Uiso 1 calc R . C6 C -0.3046(15) -0.6030(7) -0.0311(3) 0.052(2) Uani 1 d . . H6A H -0.4155(15) -0.6602(7) -0.0412(3) 0.062 Uiso 1 calc R . H6B H -0.3104(15) -0.5890(7) 0.0075(3) 0.062 Uiso 1 calc R . N7 N -0.3238(11) -0.4878(5) -0.0616(2) 0.0410(15) Uani 1 d . . C8 C -0.4958(12) -0.4218(6) -0.0627(2) 0.0334(15) Uani 1 d . . O8 O -0.6585(9) -0.4460(5) -0.0351(2) 0.0443(13) Uani 1 d . . C9 C -0.5043(11) -0.3106(6) -0.0999(2) 0.0314(14) Uani 1 d . . H9A H -0.6473(11) -0.3062(6) -0.1157(2) 0.038 Uiso 1 calc R . C10 C -0.4704(12) -0.1964(6) -0.0647(3) 0.038(2) Uani 1 d . . H10A H -0.5547(12) -0.2067(6) -0.0318(3) 0.046 Uiso 1 calc R . O10 O -0.2540(11) -0.1973(5) -0.0499(2) 0.061(2) Uani 1 d D . H10B H -0.2368(180) -0.1458(66) -0.0220(24) 0.082(33) Uiso 1 d D . C11 C -0.5420(8) -0.0785(3) -0.0914(2) 0.040(2) Uani 1 d G . C12 C -0.3963(7) 0.0146(4) -0.1003(2) 0.056(2) Uani 1 d G . H12A H -0.2559(8) 0.0062(6) -0.0888(4) 0.068 Uiso 1 calc R . C13 C -0.4606(9) 0.1204(4) -0.1263(3) 0.070(3) Uani 1 d G . H13A H -0.3631(11) 0.1828(5) -0.1323(4) 0.084 Uiso 1 calc R . C14 C -0.6704(10) 0.1330(4) -0.1435(2) 0.068(3) Uani 1 d G . H14A H -0.7134(13) 0.2038(5) -0.1610(3) 0.081 Uiso 1 calc R . C15 C -0.8161(7) 0.0399(5) -0.1346(2) 0.063(2) Uani 1 d G . H15A H -0.9565(8) 0.0483(7) -0.1461(4) 0.075 Uiso 1 calc R . C16 C -0.7518(7) -0.0659(4) -0.1085(2) 0.054(2) Uani 1 d G . H16A H -0.8493(9) -0.1283(5) -0.1026(3) 0.064 Uiso 1 calc R . C17 C -0.3870(8) -0.2441(4) -0.1910(2) 0.034(2) Uani 1 d G . C18 C -0.2328(7) -0.1628(4) -0.2090(2) 0.048(2) Uani 1 d G . H18A H -0.1000(7) -0.1603(6) -0.1923(3) 0.058 Uiso 1 calc R . C19 C -0.2771(8) -0.0852(4) -0.2518(2) 0.060(2) Uani 1 d G . H19A H -0.1739(11) -0.0308(6) -0.2639(3) 0.072 Uiso 1 calc R . C20 C -0.4756(9) -0.0890(4) -0.2768(2) 0.062(3) Uani 1 d G . H20A H -0.5052(12) -0.0371(6) -0.3054(2) 0.074 Uiso 1 calc R . C21 C -0.6298(7) -0.1703(5) -0.2588(2) 0.059(2) Uani 1 d G . H21A H -0.7626(8) -0.1728(7) -0.2755(3) 0.071 Uiso 1 calc R . C22 C -0.5855(7) -0.2478(4) -0.2159(2) 0.044(2) Uani 1 d G . H22A H -0.6887(9) -0.3022(6) -0.2039(3) 0.053 Uiso 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 N1 0.033(3) 0.035(3) 0.026(2) 0.003(2) 0.002(2) 0.001(3) C2 0.030(3) 0.039(3) 0.043(4) 0.003(3) 0.000(3) -0.005(3) O2 0.043(3) 0.052(3) 0.065(3) 0.013(3) 0.023(3) 0.016(3) C3 0.036(4) 0.044(4) 0.035(3) -0.006(3) -0.002(3) -0.007(3) C4 0.049(5) 0.040(3) 0.054(4) 0.006(4) 0.004(4) 0.011(4) C5 0.063(5) 0.035(3) 0.058(5) 0.008(4) -0.010(4) 0.015(4) C6 0.064(6) 0.036(4) 0.056(5) 0.019(4) 0.002(4) 0.003(4) N7 0.049(4) 0.031(3) 0.044(3) 0.008(3) 0.003(3) 0.002(3) C8 0.042(4) 0.033(3) 0.025(3) 0.000(3) 0.005(3) -0.003(3) O8 0.045(3) 0.044(3) 0.044(3) 0.005(2) 0.013(3) -0.007(3) C9 0.033(3) 0.032(3) 0.030(3) -0.002(3) 0.000(3) -0.002(3) C10 0.045(4) 0.036(3) 0.034(3) -0.005(3) -0.006(3) 0.006(4) O10 0.065(4) 0.048(3) 0.070(4) -0.020(3) -0.030(3) 0.009(3) C11 0.045(4) 0.036(3) 0.037(3) -0.006(3) 0.001(3) -0.002(3) C12 0.052(5) 0.045(4) 0.071(5) -0.002(4) -0.012(4) -0.010(4) C13 0.077(7) 0.046(5) 0.087(7) 0.015(5) -0.007(6) -0.009(5) C14 0.097(8) 0.038(4) 0.068(5) 0.004(4) 0.011(6) 0.016(5) C15 0.051(5) 0.058(5) 0.079(6) 0.006(5) -0.006(5) 0.011(4) C16 0.039(4) 0.046(4) 0.076(5) 0.001(4) 0.003(4) 0.001(4) C17 0.039(4) 0.036(3) 0.026(3) 0.000(3) 0.002(3) 0.000(3) C18 0.060(5) 0.038(4) 0.047(4) 0.001(3) 0.001(4) -0.012(4) C19 0.086(7) 0.042(4) 0.052(4) 0.020(4) 0.017(5) 0.003(5) C20 0.086(7) 0.061(5) 0.038(4) 0.015(4) -0.002(5) 0.024(6) C21 0.053(5) 0.085(6) 0.038(4) 0.010(4) 0.001(4) 0.015(5) C22 0.044(4) 0.047(4) 0.042(4) 0.010(4) 0.007(4) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.353(9) . ? N1 C17 1.439(6) . ? N1 C9 1.482(8) . ? C2 O2 1.204(9) . ? C2 C3 1.520(10) . ? C3 N7 1.458(9) . ? C3 C4 1.520(10) . ? C4 C5 1.523(11) . ? C5 C6 1.545(12) . ? C6 N7 1.480(8) . ? N7 C8 1.301(9) . ? C8 O8 1.257(9) . ? C8 C9 1.531(9) . ? C9 C10 1.543(9) . ? C10 O10 1.406(10) . ? C10 C11 1.521(8) . ? C11 C12 1.39 . ? C11 C16 1.39 . ? C12 C13 1.39 . ? C13 C14 1.39 . ? C14 C15 1.39 . ? C15 C16 1.39 . ? C17 C18 1.39 . ? C17 C22 1.39 . ? C18 C19 1.39 . ? C19 C20 1.39 . ? C20 C21 1.39 . ? C21 C22 1.39 . ? 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 N1 C17 118.8(5) . . ? C2 N1 C9 124.4(5) . . ? C17 N1 C9 116.5(5) . . ? O2 C2 N1 124.3(7) . . ? O2 C2 C3 119.4(7) . . ? N1 C2 C3 116.3(6) . . ? N7 C3 C4 103.1(6) . . ? N7 C3 C2 114.7(6) . . ? C4 C3 C2 114.4(6) . . ? C3 C4 C5 101.3(6) . . ? C4 C5 C6 106.3(6) . . ? N7 C6 C5 101.8(6) . . ? C8 N7 C3 124.1(5) . . ? C8 N7 C6 123.8(6) . . ? C3 N7 C6 112.1(6) . . ? O8 C8 N7 122.9(6) . . ? O8 C8 C9 117.9(6) . . ? N7 C8 C9 119.1(6) . . ? N1 C9 C8 111.9(5) . . ? N1 C9 C10 112.5(6) . . ? C8 C9 C10 107.8(5) . . ? O10 C10 C11 113.9(6) . . ? O10 C10 C9 105.9(6) . . ? C11 C10 C9 114.1(5) . . ? C12 C11 C16 120.0 . . ? C12 C11 C10 120.2(4) . . ? C16 C11 C10 119.8(4) . . ? C13 C12 C11 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C11 120.0 . . ? C18 C17 C22 120.0 . . ? C18 C17 N1 120.4(4) . . ? C22 C17 N1 119.4(4) . . ? C19 C18 C17 120.0 . . ? C18 C19 C20 120.0 . . ? C21 C20 C19 120.0 . . ? C22 C21 C20 120.0 . . ? C21 C22 C17 120.0 . . ? _refine_diff_density_max 0.209 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.056