# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ma Chen' _publ_contact_author_email chenma@sdu.edu.cn loop_ _publ_author_name 'Ma Chen' 'Aiping Huang' data_test-5e _database_code_depnum_ccdc_archive 'CCDC 829636' #TrackingRef 'test-5e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 F N2 O' _chemical_formula_weight 292.30 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' F F 0.0171 0.0103 '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 8.023 _cell_length_b 15.891 _cell_length_c 22.670 _cell_angle_alpha 90.00 _cell_angle_beta 97.96 _cell_angle_gamma 90.00 _cell_volume 2862.5 _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9906 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12000 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3301 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0698P)^2^+1.0214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3301 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 F1 F 0.01147(19) 0.15728(8) 0.44908(6) 0.0999(5) Uani 1 1 d . . . N1 N 0.20035(18) 0.37050(8) 0.32598(6) 0.0490(3) Uani 1 1 d . . . C001 C 0.1952(2) 0.22291(10) 0.29604(8) 0.0511(4) Uani 1 1 d . . . C002 C 0.1804(2) 0.43326(9) 0.37059(7) 0.0465(4) Uani 1 1 d . . . C003 C 0.1684(2) 0.28491(9) 0.33722(7) 0.0470(4) Uani 1 1 d . . . C004 C 0.2508(2) 0.39784(11) 0.27303(8) 0.0544(4) Uani 1 1 d . . . C005 C 0.2769(2) 0.33288(11) 0.23093(8) 0.0554(4) Uani 1 1 d . . . C006 C 0.1069(2) 0.26102(11) 0.38925(8) 0.0569(4) Uani 1 1 d . . . H006 H 0.0888 0.3011 0.4175 0.068 Uiso 1 1 calc R . . N2 N 0.25537(18) 0.24877(9) 0.24368(6) 0.0551(4) Uani 1 1 d . . . O1 O 0.2730(2) 0.47274(8) 0.26415(6) 0.0764(4) Uani 1 1 d . . . C007 C 0.1458(2) 0.55514(11) 0.45618(8) 0.0574(5) Uani 1 1 d . . . C008 C 0.0735(3) 0.17813(12) 0.39829(10) 0.0665(5) Uani 1 1 d . . . C009 C 0.0358(2) 0.55108(11) 0.40384(9) 0.0599(5) Uani 1 1 d . . . H009 H -0.0509 0.5902 0.3971 0.072 Uiso 1 1 calc R . . C010 C 0.2921(2) 0.43571(11) 0.42267(8) 0.0551(4) Uani 1 1 d . . . H010 H 0.3800 0.3972 0.4290 0.066 Uiso 1 1 calc R . . C011 C 0.0963(3) 0.11630(11) 0.35814(11) 0.0725(6) Uani 1 1 d . . . H011 H 0.0708 0.0605 0.3653 0.087 Uiso 1 1 calc R . . C012 C 0.1580(2) 0.13914(11) 0.30694(10) 0.0662(5) Uani 1 1 d . . . H012 H 0.1752 0.0981 0.2791 0.079 Uiso 1 1 calc R . . C013 C 0.2729(2) 0.49554(12) 0.46526(8) 0.0605(5) Uani 1 1 d . . . H013 H 0.3465 0.4959 0.5007 0.073 Uiso 1 1 calc R . . C014 C 0.0509(2) 0.49056(10) 0.36123(8) 0.0543(4) Uani 1 1 d . . . H014 H -0.0258 0.4885 0.3265 0.065 Uiso 1 1 calc R . . C015 C 0.3341(3) 0.33773(15) 0.17690(9) 0.0726(6) Uani 1 1 d . . . H015 H 0.3589 0.3867 0.1574 0.087 Uiso 1 1 calc R . . C016 C 0.2997(3) 0.20161(14) 0.19809(9) 0.0721(6) Uani 1 1 d . . . H016 H 0.2974 0.1432 0.1957 0.087 Uiso 1 1 calc R . . C017 C 0.1285(3) 0.62208(13) 0.50212(10) 0.0821(7) Uani 1 1 d . . . H01A H 0.2155 0.6150 0.5354 0.123 Uiso 1 1 calc R . . H01B H 0.0204 0.6172 0.5154 0.123 Uiso 1 1 calc R . . H01C H 0.1386 0.6766 0.4848 0.123 Uiso 1 1 calc R . . C018 C 0.3481(3) 0.25544(16) 0.15643(10) 0.0815(7) Uani 1 1 d . . . H018 H 0.3841 0.2399 0.1207 0.098 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 F1 0.1251(11) 0.0693(8) 0.1134(11) 0.0287(7) 0.0448(9) -0.0131(7) N1 0.0615(9) 0.0359(7) 0.0505(8) -0.0013(6) 0.0110(6) -0.0035(6) C001 0.0484(9) 0.0435(9) 0.0586(10) -0.0041(7) -0.0024(7) 0.0055(7) C002 0.0563(10) 0.0357(8) 0.0482(9) -0.0003(6) 0.0096(7) -0.0066(7) C003 0.0462(8) 0.0363(8) 0.0570(10) 0.0010(7) 0.0022(7) 0.0007(7) C004 0.0652(11) 0.0494(10) 0.0485(9) 0.0010(7) 0.0076(8) -0.0030(8) C005 0.0576(10) 0.0604(11) 0.0470(9) -0.0033(8) 0.0027(8) 0.0003(8) C006 0.0628(11) 0.0430(9) 0.0668(11) 0.0040(8) 0.0155(9) -0.0012(8) N2 0.0548(8) 0.0531(8) 0.0548(8) -0.0112(7) -0.0018(7) 0.0072(6) O1 0.1188(12) 0.0488(8) 0.0655(9) 0.0068(6) 0.0271(8) -0.0121(7) C007 0.0668(11) 0.0495(10) 0.0598(11) -0.0098(8) 0.0229(9) -0.0168(9) C008 0.0698(12) 0.0485(10) 0.0820(14) 0.0151(10) 0.0128(10) -0.0019(9) C009 0.0614(11) 0.0465(10) 0.0738(13) -0.0034(8) 0.0159(9) 0.0013(8) C010 0.0529(10) 0.0537(10) 0.0581(10) -0.0011(8) 0.0054(8) -0.0004(8) C011 0.0802(14) 0.0380(9) 0.0961(16) 0.0110(10) 0.0008(12) -0.0019(9) C012 0.0691(12) 0.0413(9) 0.0829(14) -0.0090(9) -0.0080(10) 0.0110(8) C013 0.0620(11) 0.0673(11) 0.0512(10) -0.0055(8) 0.0050(8) -0.0143(9) C014 0.0582(10) 0.0463(9) 0.0569(10) -0.0017(7) 0.0033(8) -0.0015(8) C015 0.0760(13) 0.0901(15) 0.0519(11) -0.0070(10) 0.0095(10) -0.0025(11) C016 0.0739(13) 0.0761(14) 0.0638(12) -0.0214(11) 0.0004(10) 0.0139(11) C017 0.1069(18) 0.0690(13) 0.0771(14) -0.0240(11) 0.0358(13) -0.0190(12) C018 0.0754(14) 0.1103(18) 0.0585(12) -0.0276(13) 0.0079(10) 0.0122(13) _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 F1 C008 1.357(2) . ? N1 C004 1.389(2) . ? N1 C003 1.4136(19) . ? N1 C002 1.445(2) . ? C001 C012 1.394(3) . ? C001 C003 1.394(2) . ? C001 N2 1.403(2) . ? C002 C014 1.376(2) . ? C002 C010 1.380(2) . ? C003 C006 1.393(2) . ? C004 O1 1.224(2) . ? C004 C005 1.441(2) . ? C005 C015 1.368(3) . ? C005 N2 1.383(2) . ? C006 C008 1.365(2) . ? C006 H006 0.9300 . ? N2 C016 1.363(2) . ? C007 C009 1.379(3) . ? C007 C013 1.386(3) . ? C007 C017 1.509(3) . ? C008 C011 1.369(3) . ? C009 C014 1.380(2) . ? C009 H009 0.9300 . ? C010 C013 1.379(3) . ? C010 H010 0.9300 . ? C011 C012 1.372(3) . ? C011 H011 0.9300 . ? C012 H012 0.9300 . ? C013 H013 0.9300 . ? C014 H014 0.9300 . ? C015 C018 1.397(3) . ? C015 H015 0.9300 . ? C016 C018 1.370(3) . ? C016 H016 0.9300 . ? C017 H01A 0.9600 . ? C017 H01B 0.9600 . ? C017 H01C 0.9600 . ? C018 H018 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 C004 N1 C003 122.58(14) . . ? C004 N1 C002 117.57(13) . . ? C003 N1 C002 119.85(13) . . ? C012 C001 C003 119.96(18) . . ? C012 C001 N2 122.48(16) . . ? C003 C001 N2 117.53(15) . . ? C014 C002 C010 120.01(15) . . ? C014 C002 N1 120.22(14) . . ? C010 C002 N1 119.77(15) . . ? C006 C003 C001 118.68(15) . . ? C006 C003 N1 120.60(15) . . ? C001 C003 N1 120.71(15) . . ? O1 C004 N1 120.85(16) . . ? O1 C004 C005 123.36(17) . . ? N1 C004 C005 115.79(15) . . ? C015 C005 N2 107.97(17) . . ? C015 C005 C004 130.55(18) . . ? N2 C005 C004 121.34(16) . . ? C008 C006 C003 119.34(18) . . ? C008 C006 H006 120.3 . . ? C003 C006 H006 120.3 . . ? C016 N2 C005 108.64(17) . . ? C016 N2 C001 129.54(17) . . ? C005 N2 C001 121.82(14) . . ? C009 C007 C013 117.77(16) . . ? C009 C007 C017 121.20(19) . . ? C013 C007 C017 121.03(19) . . ? F1 C008 C006 117.74(19) . . ? F1 C008 C011 119.17(17) . . ? C006 C008 C011 123.1(2) . . ? C007 C009 C014 121.82(17) . . ? C007 C009 H009 119.1 . . ? C014 C009 H009 119.1 . . ? C002 C010 C013 119.73(17) . . ? C002 C010 H010 120.1 . . ? C013 C010 H010 120.1 . . ? C008 C011 C012 118.02(17) . . ? C008 C011 H011 121.0 . . ? C012 C011 H011 121.0 . . ? C011 C012 C001 120.92(18) . . ? C011 C012 H012 119.5 . . ? C001 C012 H012 119.5 . . ? C010 C013 C007 121.24(17) . . ? C010 C013 H013 119.4 . . ? C007 C013 H013 119.4 . . ? C002 C014 C009 119.38(16) . . ? C002 C014 H014 120.3 . . ? C009 C014 H014 120.3 . . ? C005 C015 C018 107.3(2) . . ? C005 C015 H015 126.4 . . ? C018 C015 H015 126.4 . . ? N2 C016 C018 107.94(19) . . ? N2 C016 H016 126.0 . . ? C018 C016 H016 126.0 . . ? C007 C017 H01A 109.5 . . ? C007 C017 H01B 109.5 . . ? H01A C017 H01B 109.5 . . ? C007 C017 H01C 109.5 . . ? H01A C017 H01C 109.5 . . ? H01B C017 H01C 109.5 . . ? C016 C018 C015 108.16(18) . . ? C016 C018 H018 125.9 . . ? C015 C018 H018 125.9 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.239 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052 # Attachment 'test-5g.cif' data_test-5g _database_code_depnum_ccdc_archive 'CCDC 834986' #TrackingRef 'test-5g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2 O' _chemical_formula_weight 288.34 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 9.032(2) _cell_length_b 9.319(2) _cell_length_c 9.925(2) _cell_angle_alpha 88.946(2) _cell_angle_beta 73.298(2) _cell_angle_gamma 65.822(2) _cell_volume 725.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9877 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _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_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6179 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3244 _reflns_number_gt 2317 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1221P)^2^+0.2360P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3244 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.2001 _refine_ls_wR_factor_gt 0.1758 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 C19 C 0.2291(4) 0.5056(3) 1.2793(2) 0.0630(7) Uani 1 1 d . . . H19A H 0.1965 0.4271 1.2523 0.095 Uiso 1 1 calc R . . H19B H 0.1367 0.5798 1.3547 0.095 Uiso 1 1 calc R . . H19C H 0.3276 0.4550 1.3108 0.095 Uiso 1 1 calc R . . N1 N 0.2599(2) 0.64484(19) 0.78221(16) 0.0380(4) Uani 1 1 d . . . C14 C 0.2838(2) 0.6624(2) 0.91465(18) 0.0350(4) Uani 1 1 d . . . C13 C 0.2589(2) 0.5630(2) 1.01905(19) 0.0360(4) Uani 1 1 d . . . O1 O 0.1992(2) 0.5148(2) 0.62917(16) 0.0615(5) Uani 1 1 d . . . N2 N 0.2230(2) 0.43852(19) 0.98010(17) 0.0387(4) Uani 1 1 d . . . C5 C 0.2589(3) 0.7641(2) 0.68634(19) 0.0378(4) Uani 1 1 d . . . C15 C 0.3324(3) 0.7799(2) 0.9410(2) 0.0428(5) Uani 1 1 d . . . H15 H 0.3504 0.8444 0.8714 0.051 Uiso 1 1 calc R . . C17 C 0.3199(3) 0.7096(3) 1.1746(2) 0.0512(6) Uani 1 1 d . . . H17 H 0.3306 0.7278 1.2624 0.061 Uiso 1 1 calc R . . C9 C 0.2118(3) 0.4168(2) 0.8462(2) 0.0404(5) Uani 1 1 d . . . C6 C 0.4020(3) 0.7379(3) 0.5734(2) 0.0432(5) Uani 1 1 d . . . H6 H 0.4995 0.6436 0.5579 0.052 Uiso 1 1 calc R . . C16 C 0.3540(3) 0.8013(3) 1.0699(2) 0.0513(5) Uani 1 1 d . . . H16 H 0.3913 0.8769 1.0862 0.062 Uiso 1 1 calc R . . C8 C 0.2220(3) 0.5261(2) 0.7432(2) 0.0413(5) Uani 1 1 d . . . C3 C 0.1128(3) 1.0170(3) 0.6164(3) 0.0518(6) Uani 1 1 d . . . H3 H 0.0144 1.1104 0.6312 0.062 Uiso 1 1 calc R . . C7 C 0.3983(3) 0.8542(3) 0.4832(2) 0.0495(5) Uani 1 1 d . . . H7 H 0.4949 0.8372 0.4076 0.059 Uiso 1 1 calc R . . C4 C 0.1141(3) 0.9028(3) 0.7083(2) 0.0475(5) Uani 1 1 d . . . H4 H 0.0177 0.9199 0.7843 0.057 Uiso 1 1 calc R . . C18 C 0.2705(3) 0.5918(3) 1.1538(2) 0.0444(5) Uani 1 1 d . . . C2 C 0.2545(3) 0.9946(3) 0.5033(2) 0.0484(5) Uani 1 1 d . . . C1 C 0.2504(4) 1.1217(3) 0.4055(3) 0.0737(9) Uani 1 1 d . . . H1A H 0.3586 1.0872 0.3331 0.110 Uiso 1 1 calc R . . H1B H 0.2276 1.2173 0.4587 0.110 Uiso 1 1 calc R . . H1C H 0.1623 1.1411 0.3624 0.110 Uiso 1 1 calc R . . C11 C 0.1812(3) 0.2208(3) 0.9643(3) 0.0576(6) Uani 1 1 d . . . H11 H 0.1654 0.1298 0.9873 0.069 Uiso 1 1 calc R . . C12 C 0.2044(3) 0.3150(3) 1.0503(3) 0.0546(6) Uani 1 1 d . . . H12 H 0.2075 0.2991 1.1424 0.065 Uiso 1 1 calc R . . C10 C 0.1847(3) 0.2834(3) 0.8350(3) 0.0508(6) Uani 1 1 d . . . H10 H 0.1713 0.2427 0.7567 0.061 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 C19 0.0728(16) 0.0747(17) 0.0375(11) 0.0195(11) -0.0208(11) -0.0253(13) N1 0.0493(9) 0.0388(8) 0.0316(8) 0.0096(6) -0.0136(7) -0.0235(7) C14 0.0355(9) 0.0356(9) 0.0311(9) 0.0044(7) -0.0098(7) -0.0126(8) C13 0.0337(9) 0.0351(9) 0.0332(9) 0.0055(7) -0.0089(7) -0.0097(7) O1 0.0933(13) 0.0744(11) 0.0410(9) 0.0116(8) -0.0280(8) -0.0538(10) N2 0.0394(8) 0.0348(8) 0.0385(9) 0.0112(7) -0.0092(7) -0.0144(7) C5 0.0460(11) 0.0424(10) 0.0328(9) 0.0113(8) -0.0157(8) -0.0240(9) C15 0.0477(11) 0.0390(10) 0.0430(11) 0.0061(8) -0.0145(9) -0.0193(9) C17 0.0518(13) 0.0573(13) 0.0393(11) -0.0021(10) -0.0203(10) -0.0135(11) C9 0.0428(11) 0.0366(10) 0.0394(10) 0.0042(8) -0.0075(8) -0.0179(8) C6 0.0437(11) 0.0495(11) 0.0359(10) 0.0070(8) -0.0110(8) -0.0201(9) C16 0.0540(13) 0.0492(12) 0.0537(13) -0.0035(10) -0.0196(10) -0.0221(10) C8 0.0473(11) 0.0435(11) 0.0361(10) 0.0043(8) -0.0110(8) -0.0233(9) C3 0.0550(13) 0.0437(11) 0.0569(13) 0.0159(10) -0.0213(11) -0.0186(10) C7 0.0566(13) 0.0674(14) 0.0352(10) 0.0149(10) -0.0124(9) -0.0381(12) C4 0.0454(11) 0.0501(12) 0.0442(11) 0.0126(9) -0.0098(9) -0.0203(10) C18 0.0410(11) 0.0483(11) 0.0364(10) 0.0089(9) -0.0148(8) -0.0098(9) C2 0.0682(14) 0.0538(12) 0.0446(12) 0.0212(10) -0.0285(11) -0.0394(12) C1 0.105(2) 0.0813(19) 0.0703(17) 0.0460(15) -0.0465(17) -0.0620(18) C11 0.0581(14) 0.0364(11) 0.0699(16) 0.0101(10) -0.0035(12) -0.0227(10) C12 0.0607(14) 0.0448(12) 0.0548(13) 0.0226(10) -0.0129(11) -0.0231(11) C10 0.0517(13) 0.0398(11) 0.0574(13) -0.0009(9) -0.0047(10) -0.0238(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 C19 C18 1.509(3) . ? N1 C8 1.377(3) . ? N1 C14 1.414(2) . ? N1 C5 1.449(2) . ? C14 C15 1.390(3) . ? C14 C13 1.408(2) . ? C13 C18 1.410(3) . ? C13 N2 1.413(3) . ? O1 C8 1.221(2) . ? N2 C12 1.378(3) . ? N2 C9 1.386(3) . ? C5 C4 1.375(3) . ? C5 C6 1.380(3) . ? C15 C16 1.378(3) . ? C17 C16 1.379(3) . ? C17 C18 1.382(3) . ? C9 C10 1.374(3) . ? C9 C8 1.440(3) . ? C6 C7 1.389(3) . ? C3 C2 1.381(3) . ? C3 C4 1.388(3) . ? C7 C2 1.381(3) . ? C2 C1 1.512(3) . ? C11 C12 1.351(4) . ? C11 C10 1.397(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 C8 N1 C14 123.17(15) . . ? C8 N1 C5 116.99(15) . . ? C14 N1 C5 119.59(15) . . ? C15 C14 C13 120.00(17) . . ? C15 C14 N1 119.00(16) . . ? C13 C14 N1 121.01(17) . . ? C14 C13 C18 119.48(18) . . ? C14 C13 N2 116.53(16) . . ? C18 C13 N2 123.99(18) . . ? C12 N2 C9 106.57(18) . . ? C12 N2 C13 131.86(18) . . ? C9 N2 C13 121.43(16) . . ? C4 C5 C6 120.47(18) . . ? C4 C5 N1 119.43(17) . . ? C6 C5 N1 120.11(18) . . ? C16 C15 C14 120.26(19) . . ? C16 C17 C18 122.50(19) . . ? C10 C9 N2 109.09(18) . . ? C10 C9 C8 128.6(2) . . ? N2 C9 C8 122.30(18) . . ? C5 C6 C7 119.1(2) . . ? C15 C16 C17 119.4(2) . . ? O1 C8 N1 122.03(18) . . ? O1 C8 C9 122.79(19) . . ? N1 C8 C9 115.18(17) . . ? C2 C3 C4 121.3(2) . . ? C2 C7 C6 121.6(2) . . ? C5 C4 C3 119.5(2) . . ? C17 C18 C13 118.10(19) . . ? C17 C18 C19 117.1(2) . . ? C13 C18 C19 124.8(2) . . ? C7 C2 C3 118.06(18) . . ? C7 C2 C1 121.6(2) . . ? C3 C2 C1 120.3(2) . . ? C12 C11 C10 108.4(2) . . ? C11 C12 N2 109.3(2) . . ? C9 C10 C11 106.6(2) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.404 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.044