data_Compound_11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O' _chemical_formula_weight 263.33 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4218(8) _cell_length_b 9.0810(8) _cell_length_c 9.1550(8) _cell_angle_alpha 97.508(7) _cell_angle_beta 101.043(7) _cell_angle_gamma 90.621(7) _cell_volume 680.84(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.5159 _cell_measurement_theta_max 32.4053 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.97455 _exptl_absorpt_correction_T_max 0.98086 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6754 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_sigmaI/netI 0.0095 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.53 _diffrn_reflns_theta_max 32.48 _reflns_number_total 4242 _reflns_number_gt 4152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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^)+(0.0609P)^2^+0.1822P] 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 4242 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 N1 N 0.34520(9) 0.30931(8) 0.77928(9) 0.02193(15) Uani 1 1 d . . . C2 C 0.36741(10) 0.45585(9) 0.74335(9) 0.02115(16) Uani 1 1 d . . . C3 C 0.52126(11) 0.50014(10) 0.72498(11) 0.02749(19) Uani 1 1 d . . . H3A H 0.6056 0.4312 0.7312 0.033 Uiso 1 1 calc R . . C4 C 0.55219(13) 0.64357(11) 0.69772(12) 0.0306(2) Uani 1 1 d . . . H4A H 0.6570 0.6722 0.6851 0.037 Uiso 1 1 calc R . . C5 C 0.42986(13) 0.74498(10) 0.68890(11) 0.0291(2) Uani 1 1 d . . . H5A H 0.4505 0.8432 0.6704 0.035 Uiso 1 1 calc R . . C6 C 0.27704(12) 0.70173(10) 0.70735(10) 0.02623(18) Uani 1 1 d . . . H6A H 0.1935 0.7714 0.7003 0.031 Uiso 1 1 calc R . . C7 C 0.24245(11) 0.55783(9) 0.73612(9) 0.02216(16) Uani 1 1 d . . . C8 C 0.07968(11) 0.52051(10) 0.76530(11) 0.02588(18) Uani 1 1 d . . . C9 C -0.01425(12) 0.38464(11) 0.67570(13) 0.0314(2) Uani 1 1 d . . . H9A H -0.1014 0.4173 0.5991 0.038 Uiso 1 1 calc R . . H9B H -0.0663 0.3330 0.7440 0.038 Uiso 1 1 calc R . . C10 C 0.08823(11) 0.27403(10) 0.59675(11) 0.02707(18) Uani 1 1 d . . . H10A H 0.0175 0.1908 0.5374 0.032 Uiso 1 1 calc R . . H10B H 0.1392 0.3240 0.5266 0.032 Uiso 1 1 calc R . . C11 C 0.21826(11) 0.21374(9) 0.70893(10) 0.02315(17) Uani 1 1 d . . . O11 O 0.21073(9) 0.08614(8) 0.73865(9) 0.03151(17) Uani 1 1 d . . . C12 C 0.46757(11) 0.25333(9) 0.89374(9) 0.02316(17) Uani 1 1 d . . . H12A H 0.4111 0.2017 0.9590 0.028 Uiso 1 1 calc R . . H12B H 0.5298 0.3394 0.9573 0.028 Uiso 1 1 calc R . . C13 C 0.58593(10) 0.14809(9) 0.83451(9) 0.02041(16) Uani 1 1 d . . . C14 C 0.60723(11) 0.13139(9) 0.68595(10) 0.02366(17) Uani 1 1 d . . . H14A H 0.5404 0.1828 0.6149 0.028 Uiso 1 1 calc R . . C15 C 0.72588(12) 0.03977(10) 0.64067(11) 0.02801(19) Uani 1 1 d . . . H15A H 0.7398 0.0294 0.5393 0.034 Uiso 1 1 calc R . . C16 C 0.82379(11) -0.03640(11) 0.74382(12) 0.0300(2) Uani 1 1 d . . . H16A H 0.9070 -0.0961 0.7140 0.036 Uiso 1 1 calc R . . C17 C 0.79930(11) -0.02467(10) 0.89097(12) 0.02842(19) Uani 1 1 d . . . H17A H 0.8633 -0.0795 0.9607 0.034 Uiso 1 1 calc R . . C18 C 0.68141(11) 0.06705(10) 0.93621(10) 0.02409(17) Uani 1 1 d . . . H18A H 0.6656 0.0747 1.0369 0.029 Uiso 1 1 calc R . . C19 C 0.01683(14) 0.60944(13) 0.86626(14) 0.0379(2) Uani 1 1 d . . . H19A H 0.0760 0.6962 0.9192 0.045 Uiso 1 1 calc R . . H19B H -0.0869 0.5859 0.8851 0.045 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 N1 0.0227(3) 0.0173(3) 0.0256(3) 0.0044(2) 0.0031(3) 0.0015(2) C2 0.0243(4) 0.0166(3) 0.0221(4) 0.0019(3) 0.0040(3) 0.0003(3) C3 0.0265(4) 0.0211(4) 0.0355(5) 0.0010(3) 0.0096(3) -0.0011(3) C4 0.0344(5) 0.0244(4) 0.0340(5) 0.0011(3) 0.0115(4) -0.0067(3) C5 0.0415(5) 0.0197(4) 0.0253(4) 0.0033(3) 0.0046(4) -0.0051(3) C6 0.0337(4) 0.0188(4) 0.0241(4) 0.0036(3) -0.0002(3) 0.0012(3) C7 0.0254(4) 0.0185(3) 0.0214(3) 0.0026(3) 0.0017(3) 0.0018(3) C8 0.0234(4) 0.0232(4) 0.0304(4) 0.0052(3) 0.0024(3) 0.0040(3) C9 0.0235(4) 0.0276(4) 0.0408(5) 0.0009(4) 0.0026(4) 0.0007(3) C10 0.0273(4) 0.0234(4) 0.0279(4) 0.0009(3) 0.0006(3) -0.0012(3) C11 0.0247(4) 0.0192(3) 0.0257(4) 0.0019(3) 0.0062(3) 0.0000(3) O11 0.0341(4) 0.0205(3) 0.0404(4) 0.0075(3) 0.0064(3) -0.0027(2) C12 0.0265(4) 0.0215(4) 0.0212(4) 0.0029(3) 0.0039(3) 0.0048(3) C13 0.0214(3) 0.0168(3) 0.0223(4) 0.0013(3) 0.0031(3) -0.0002(3) C14 0.0272(4) 0.0204(4) 0.0236(4) 0.0030(3) 0.0057(3) 0.0006(3) C15 0.0302(4) 0.0249(4) 0.0303(4) 0.0001(3) 0.0119(3) -0.0010(3) C16 0.0236(4) 0.0255(4) 0.0411(5) 0.0004(4) 0.0096(4) 0.0023(3) C17 0.0238(4) 0.0246(4) 0.0347(5) 0.0035(3) 0.0004(3) 0.0035(3) C18 0.0250(4) 0.0220(4) 0.0236(4) 0.0024(3) 0.0010(3) 0.0014(3) C19 0.0336(5) 0.0343(5) 0.0460(6) -0.0013(4) 0.0128(4) 0.0053(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 C11 1.3715(11) . ? N1 C2 1.4306(10) . ? N1 C12 1.4682(11) . ? C2 C3 1.3996(12) . ? C2 C7 1.4071(12) . ? C3 C4 1.3889(13) . ? C4 C5 1.3871(15) . ? C5 C6 1.3889(14) . ? C6 C7 1.4046(12) . ? C7 C8 1.4897(13) . ? C8 C19 1.3372(14) . ? C8 C9 1.5122(14) . ? C9 C10 1.5311(14) . ? C10 C11 1.5108(13) . ? C11 O11 1.2281(11) . ? C12 C13 1.5144(12) . ? C13 C14 1.3947(12) . ? C13 C18 1.4001(11) . ? C14 C15 1.3961(12) . ? C15 C16 1.3910(14) . ? C16 C17 1.3922(15) . ? C17 C18 1.3916(13) . ? 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 C11 N1 C2 123.94(7) . . ? C11 N1 C12 116.99(7) . . ? C2 N1 C12 119.02(7) . . ? C3 C2 C7 119.91(8) . . ? C3 C2 N1 118.25(8) . . ? C7 C2 N1 121.70(8) . . ? C4 C3 C2 120.82(9) . . ? C5 C4 C3 119.95(9) . . ? C4 C5 C6 119.47(8) . . ? C5 C6 C7 121.87(9) . . ? C6 C7 C2 117.96(8) . . ? C6 C7 C8 119.60(8) . . ? C2 C7 C8 122.37(8) . . ? C19 C8 C7 119.84(9) . . ? C19 C8 C9 121.07(9) . . ? C7 C8 C9 119.05(8) . . ? C8 C9 C10 114.34(8) . . ? C11 C10 C9 111.15(8) . . ? O11 C11 N1 120.92(8) . . ? O11 C11 C10 122.18(8) . . ? N1 C11 C10 116.89(7) . . ? N1 C12 C13 115.66(7) . . ? C14 C13 C18 118.86(8) . . ? C14 C13 C12 123.40(7) . . ? C18 C13 C12 117.71(7) . . ? C13 C14 C15 120.59(8) . . ? C16 C15 C14 120.06(9) . . ? C15 C16 C17 119.69(8) . . ? C18 C17 C16 120.21(9) . . ? C17 C18 C13 120.51(8) . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 32.48 _diffrn_measured_fraction_theta_full 0.861 _refine_diff_density_max 0.355 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.040 #===END data_Compound_12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O' _chemical_formula_weight 277.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.5637(12) _cell_length_b 6.9794(6) _cell_length_c 27.0219(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.622(6) _cell_angle_gamma 90.00 _cell_volume 3070.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.7777 _cell_measurement_theta_max 32.6924 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12773 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0112 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 32.70 _reflns_number_total 5197 _reflns_number_gt 5101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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^)+(0.0479P)^2^+2.3150P] 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 5197 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 N1 N 0.30066(5) 0.00278(13) 0.11825(3) 0.02693(17) Uani 1 1 d . . . C2 C 0.38082(6) 0.08578(13) 0.12488(4) 0.02413(18) Uani 1 1 d . . . C3 C 0.40953(7) 0.19119(16) 0.16845(4) 0.0315(2) Uani 1 1 d . . . H3A H 0.3771 0.2013 0.1939 0.038 Uiso 1 1 calc R . . C4 C 0.48543(8) 0.28121(18) 0.17470(5) 0.0389(3) Uani 1 1 d . . . H4A H 0.5041 0.3561 0.2039 0.047 Uiso 1 1 calc R . . C5 C 0.53401(7) 0.26200(19) 0.13832(5) 0.0397(3) Uani 1 1 d . . . H5A H 0.5864 0.3219 0.1428 0.048 Uiso 1 1 calc R . . C6 C 0.50589(6) 0.15516(17) 0.09540(4) 0.0328(2) Uani 1 1 d . . . H6A H 0.5400 0.1403 0.0710 0.039 Uiso 1 1 calc R . . C7 C 0.42838(6) 0.06866(14) 0.08724(4) 0.02535(18) Uani 1 1 d . . . C8 C 0.39910(7) -0.03750(16) 0.03922(4) 0.0297(2) Uani 1 1 d . . . C9 C 0.42598(8) -0.24403(18) 0.03731(5) 0.0394(3) Uani 1 1 d . . . H9A H 0.4834 -0.2557 0.0555 0.047 Uiso 1 1 calc R . . H9B H 0.4249 -0.2802 0.0018 0.047 Uiso 1 1 calc R . . C10 C 0.37221(9) -0.38452(17) 0.06035(5) 0.0404(3) Uani 1 1 d . . . H10A H 0.3991 -0.5118 0.0633 0.049 Uiso 1 1 calc R . . H10B H 0.3188 -0.3978 0.0371 0.049 Uiso 1 1 calc R . . C11 C 0.35613(8) -0.32480(16) 0.11250(5) 0.0367(2) Uani 1 1 d . . . H11A H 0.3443 -0.4404 0.1312 0.044 Uiso 1 1 calc R . . H11B H 0.4061 -0.2638 0.1318 0.044 Uiso 1 1 calc R . . C12 C 0.28493(7) -0.18697(17) 0.10865(4) 0.0328(2) Uani 1 1 d . . . O12 O 0.21395(6) -0.24569(16) 0.09778(4) 0.0511(3) Uani 1 1 d . . . C13 C 0.23051(6) 0.13385(18) 0.11417(4) 0.0314(2) Uani 1 1 d . . . H13A H 0.1869 0.0889 0.0865 0.038 Uiso 1 1 calc R . . H13B H 0.2481 0.2622 0.1047 0.038 Uiso 1 1 calc R . . C14 C 0.19426(6) 0.15345(15) 0.16147(4) 0.02579(19) Uani 1 1 d . . . C15 C 0.21668(7) 0.03795(16) 0.20335(4) 0.0318(2) Uani 1 1 d . . . H15A H 0.2581 -0.0565 0.2036 0.038 Uiso 1 1 calc R . . C16 C 0.17910(8) 0.05885(19) 0.24525(5) 0.0377(2) Uani 1 1 d . . . H16A H 0.1955 -0.0200 0.2740 0.045 Uiso 1 1 calc R . . C17 C 0.11823(8) 0.1936(2) 0.24499(5) 0.0419(3) Uani 1 1 d . . . H17A H 0.0919 0.2062 0.2732 0.050 Uiso 1 1 calc R . . C18 C 0.09574(9) 0.3098(2) 0.20360(6) 0.0492(3) Uani 1 1 d . . . H18A H 0.0539 0.4031 0.2033 0.059 Uiso 1 1 calc R . . C19 C 0.13397(8) 0.2913(2) 0.16214(5) 0.0407(3) Uani 1 1 d . . . H19A H 0.1187 0.3738 0.1340 0.049 Uiso 1 1 calc R . . C20 C 0.35283(8) 0.0499(2) 0.00033(5) 0.0403(3) Uani 1 1 d . . . H20A H 0.3382 0.1806 0.0029 0.048 Uiso 1 1 calc R . . H20B H 0.3344 -0.0184 -0.0301 0.048 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 N1 0.0225(4) 0.0273(4) 0.0316(4) -0.0036(3) 0.0065(3) -0.0016(3) C2 0.0223(4) 0.0210(4) 0.0288(4) -0.0012(3) 0.0040(3) -0.0002(3) C3 0.0312(5) 0.0291(5) 0.0339(5) -0.0080(4) 0.0053(4) -0.0015(4) C4 0.0372(6) 0.0336(5) 0.0431(6) -0.0088(5) 0.0000(5) -0.0084(4) C5 0.0293(5) 0.0387(6) 0.0492(7) 0.0019(5) 0.0019(4) -0.0114(4) C6 0.0265(4) 0.0346(5) 0.0381(5) 0.0060(4) 0.0082(4) -0.0026(4) C7 0.0250(4) 0.0232(4) 0.0280(4) 0.0026(3) 0.0051(3) 0.0011(3) C8 0.0321(5) 0.0297(5) 0.0289(5) -0.0013(4) 0.0100(4) -0.0008(4) C9 0.0483(7) 0.0343(6) 0.0391(6) -0.0050(5) 0.0175(5) 0.0060(5) C10 0.0562(7) 0.0255(5) 0.0419(6) -0.0070(4) 0.0151(5) 0.0017(5) C11 0.0537(7) 0.0228(4) 0.0361(5) -0.0009(4) 0.0147(5) -0.0029(4) C12 0.0369(5) 0.0325(5) 0.0317(5) -0.0084(4) 0.0130(4) -0.0108(4) O12 0.0423(5) 0.0563(6) 0.0587(6) -0.0247(5) 0.0198(4) -0.0247(4) C13 0.0244(4) 0.0391(6) 0.0308(5) 0.0044(4) 0.0052(3) 0.0042(4) C14 0.0204(4) 0.0273(4) 0.0293(4) -0.0010(3) 0.0032(3) -0.0006(3) C15 0.0320(5) 0.0300(5) 0.0338(5) 0.0035(4) 0.0075(4) 0.0036(4) C16 0.0411(6) 0.0399(6) 0.0330(5) 0.0026(5) 0.0093(4) -0.0047(5) C17 0.0365(6) 0.0542(8) 0.0373(6) -0.0102(5) 0.0131(5) -0.0041(5) C18 0.0410(6) 0.0579(8) 0.0501(7) -0.0060(6) 0.0123(5) 0.0189(6) C19 0.0379(6) 0.0454(7) 0.0385(6) 0.0042(5) 0.0060(5) 0.0168(5) C20 0.0468(6) 0.0411(6) 0.0311(5) -0.0017(5) 0.0028(5) 0.0004(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 N1 C12 1.3653(14) . ? N1 C2 1.4293(12) . ? N1 C13 1.4669(13) . ? C2 C3 1.3956(14) . ? C2 C7 1.4017(14) . ? C3 C4 1.3876(16) . ? C4 C5 1.3868(19) . ? C5 C6 1.3853(17) . ? C6 C7 1.3989(14) . ? C7 C8 1.4952(15) . ? C8 C20 1.3293(16) . ? C8 C9 1.5123(16) . ? C9 C10 1.5318(18) . ? C10 C11 1.5392(17) . ? C11 C12 1.5105(17) . ? C12 O12 1.2285(14) . ? C13 C14 1.5153(15) . ? C14 C15 1.3832(15) . ? C14 C19 1.3892(15) . ? C15 C16 1.3965(16) . ? C16 C17 1.3779(19) . ? C17 C18 1.376(2) . ? C18 C19 1.3906(19) . ? 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 C12 N1 C2 123.87(9) . . ? C12 N1 C13 118.03(9) . . ? C2 N1 C13 117.47(8) . . ? C3 C2 C7 120.50(9) . . ? C3 C2 N1 118.92(9) . . ? C7 C2 N1 120.52(8) . . ? C4 C3 C2 120.10(10) . . ? C5 C4 C3 120.07(11) . . ? C6 C5 C4 119.74(10) . . ? C5 C6 C7 121.44(10) . . ? C6 C7 C2 118.10(9) . . ? C6 C7 C8 119.49(9) . . ? C2 C7 C8 122.42(9) . . ? C20 C8 C7 120.41(10) . . ? C20 C8 C9 122.74(11) . . ? C7 C8 C9 116.84(10) . . ? C8 C9 C10 113.54(10) . . ? C9 C10 C11 114.23(10) . . ? C12 C11 C10 111.97(10) . . ? O12 C12 N1 120.64(12) . . ? O12 C12 C11 120.31(11) . . ? N1 C12 C11 119.04(10) . . ? N1 C13 C14 115.11(9) . . ? C15 C14 C19 118.57(10) . . ? C15 C14 C13 123.31(9) . . ? C19 C14 C13 118.10(10) . . ? C14 C15 C16 120.65(10) . . ? C17 C16 C15 120.15(11) . . ? C18 C17 C16 119.64(11) . . ? C17 C18 C19 120.31(12) . . ? C14 C19 C18 120.66(12) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 32.70 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.313 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.040 #===END