# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 F3 N O2' _chemical_formula_weight 375.38 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' F F 0.0171 0.0103 '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 6.1860(5) _cell_length_b 9.6029(9) _cell_length_c 16.4251(11) _cell_angle_alpha 77.495(6) _cell_angle_beta 80.955(6) _cell_angle_gamma 87.557(7) _cell_volume 940.68(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _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 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 5416 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3279 _reflns_number_gt 1579 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1996P)^2^+0.0998P] 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 3279 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1723 _refine_ls_R_factor_gt 0.0993 _refine_ls_wR_factor_ref 0.3474 _refine_ls_wR_factor_gt 0.2961 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _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 C6 C 0.9000(7) 0.4675(5) 0.3283(3) 0.0590(12) Uani 1 1 d . . . N1 N 0.7524(6) 0.5726(5) 0.4452(2) 0.0720(12) Uani 1 1 d . . . H1A H 0.6522 0.5786 0.4870 0.086 Uiso 1 1 calc R . . C5 C 1.0716(7) 0.5568(5) 0.3114(3) 0.0616(12) Uani 1 1 d . . . O2 O 0.5559(6) 0.4038(4) 0.4146(2) 0.0816(11) Uani 1 1 d . . . O1 O 1.2341(5) 0.5594(4) 0.24422(19) 0.0761(11) Uani 1 1 d . . . C9 C 1.0960(7) 0.6569(5) 0.3632(3) 0.0638(13) Uani 1 1 d . . . C13 C 0.9492(9) 0.7505(6) 0.4860(3) 0.0761(15) Uani 1 1 d . . . H13A H 0.8403 0.7519 0.5318 0.091 Uiso 1 1 calc R . . C8 C 0.9309(8) 0.6605(6) 0.4316(3) 0.0660(13) Uani 1 1 d . . . C15 C 0.8812(8) 0.3515(5) 0.2824(3) 0.0619(12) Uani 1 1 d . . . C10 C 1.2754(8) 0.7469(5) 0.3510(3) 0.0702(14) Uani 1 1 d . . . H10A H 1.3854 0.7449 0.3056 0.084 Uiso 1 1 calc R . . C7 C 0.7223(8) 0.4769(6) 0.3978(3) 0.0673(13) Uani 1 1 d . . . C20 C 0.6992(8) 0.3396(5) 0.2453(3) 0.0697(14) Uani 1 1 d . . . H20A H 0.5839 0.4044 0.2495 0.084 Uiso 1 1 calc R . . C11 C 1.2963(8) 0.8379(6) 0.4027(3) 0.0706(14) Uani 1 1 d . . . C12 C 1.1260(10) 0.8362(6) 0.4723(3) 0.0790(15) Uani 1 1 d . . . H12A H 1.1363 0.8956 0.5093 0.095 Uiso 1 1 calc R . . C16 C 1.0485(8) 0.2510(5) 0.2771(3) 0.0726(14) Uani 1 1 d . . . H16A H 1.1712 0.2563 0.3025 0.087 Uiso 1 1 calc R . . C18 C 0.8543(10) 0.1351(6) 0.1965(3) 0.0798(16) Uani 1 1 d . . . C17 C 1.0342(10) 0.1429(6) 0.2344(4) 0.0834(16) Uani 1 1 d . . . H17A H 1.1465 0.0758 0.2315 0.100 Uiso 1 1 calc R . . C19 C 0.6867(9) 0.2329(6) 0.2024(3) 0.0811(15) Uani 1 1 d . . . H19A H 0.5639 0.2268 0.1772 0.097 Uiso 1 1 calc R . . C14 C 1.4884(10) 0.9342(7) 0.3908(4) 0.0982(19) Uani 1 1 d . . . H14A H 1.5871 0.9235 0.3412 0.147 Uiso 1 1 calc R . . H14B H 1.5627 0.9094 0.4391 0.147 Uiso 1 1 calc R . . H14C H 1.4382 1.0314 0.3844 0.147 Uiso 1 1 calc R . . C4 C 1.1754(9) 0.5933(7) 0.1619(3) 0.0912(17) Uani 1 1 d . . . H4A H 1.1013 0.5118 0.1534 0.109 Uiso 1 1 calc R . . H4B H 1.0713 0.6720 0.1593 0.109 Uiso 1 1 calc R . . F1 F 0.7972(19) -0.0995(7) 0.1954(5) 0.276(6) Uani 1 1 d . . . C21 C 0.8521(15) 0.0138(11) 0.1535(5) 0.126(3) Uani 1 1 d . . . F2 F 0.9935(17) -0.0014(9) 0.1023(5) 0.296(7) Uani 1 1 d . . . F3 F 0.696(2) 0.0329(13) 0.1095(11) 0.398(10) Uani 1 1 d . . . C1 C 1.7121(13) 0.7132(12) 0.0132(5) 0.164(4) Uani 1 1 d . . . H1B H 1.8408 0.7428 0.0306 0.246 Uiso 1 1 calc R . . H1C H 1.6575 0.7909 -0.0258 0.246 Uiso 1 1 calc R . . H1D H 1.7481 0.6339 -0.0136 0.246 Uiso 1 1 calc R . . C3 C 1.3471(14) 0.6300(14) 0.0957(4) 0.181(5) Uani 1 1 d . . . H3A H 1.3612 0.5476 0.0699 0.217 Uiso 1 1 calc R . . H3B H 1.2836 0.7044 0.0562 0.217 Uiso 1 1 calc R . . C2 C 1.5424(15) 0.6698(12) 0.0880(5) 0.165(4) Uani 1 1 d . . . H2B H 1.6111 0.5932 0.1243 0.198 Uiso 1 1 calc R . . H2C H 1.5319 0.7497 0.1158 0.198 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 C6 0.055(3) 0.065(3) 0.055(2) -0.020(2) 0.005(2) 0.015(2) N1 0.069(3) 0.086(3) 0.058(2) -0.028(2) 0.0149(19) 0.012(2) C5 0.061(3) 0.069(3) 0.055(2) -0.022(2) 0.000(2) 0.017(2) O2 0.075(2) 0.092(3) 0.072(2) -0.0293(19) 0.0224(18) -0.002(2) O1 0.0597(19) 0.110(3) 0.060(2) -0.0346(18) 0.0101(15) 0.0013(18) C9 0.061(3) 0.071(3) 0.058(3) -0.018(2) -0.004(2) 0.013(2) C13 0.089(4) 0.081(4) 0.060(3) -0.029(3) -0.002(3) 0.027(3) C8 0.072(3) 0.074(3) 0.050(2) -0.017(2) -0.001(2) 0.015(3) C15 0.063(3) 0.064(3) 0.052(2) -0.013(2) 0.010(2) 0.006(2) C10 0.073(3) 0.074(3) 0.060(3) -0.017(3) 0.000(2) 0.010(3) C7 0.065(3) 0.076(3) 0.056(3) -0.019(2) 0.008(2) 0.015(3) C20 0.061(3) 0.070(3) 0.076(3) -0.022(3) 0.002(2) 0.009(2) C11 0.074(3) 0.073(3) 0.068(3) -0.022(3) -0.014(2) 0.008(3) C12 0.098(4) 0.076(4) 0.071(3) -0.032(3) -0.018(3) 0.016(3) C16 0.070(3) 0.076(3) 0.069(3) -0.024(3) 0.005(2) 0.010(3) C18 0.087(4) 0.073(4) 0.081(3) -0.030(3) 0.008(3) -0.010(3) C17 0.091(4) 0.064(3) 0.090(4) -0.024(3) 0.008(3) 0.017(3) C19 0.079(3) 0.082(4) 0.084(3) -0.029(3) -0.001(3) -0.002(3) C14 0.108(4) 0.097(5) 0.099(4) -0.037(4) -0.024(4) 0.002(4) C4 0.097(4) 0.106(5) 0.058(3) -0.004(3) 0.008(3) 0.007(3) F1 0.488(15) 0.135(5) 0.198(6) -0.092(4) 0.087(8) -0.147(8) C21 0.142(6) 0.146(8) 0.098(5) -0.057(5) 0.018(5) -0.062(6) F2 0.413(12) 0.246(8) 0.235(7) -0.192(7) 0.172(9) -0.171(9) F3 0.496(16) 0.275(11) 0.64(2) -0.358(14) -0.433(18) 0.233(11) C1 0.123(6) 0.234(11) 0.128(6) -0.051(7) 0.035(5) -0.071(7) C3 0.116(6) 0.341(15) 0.069(4) -0.013(6) 0.017(4) -0.073(8) C2 0.127(7) 0.230(11) 0.123(7) -0.005(7) -0.001(6) -0.060(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 C6 C5 1.349(6) . ? C6 C7 1.470(6) . ? C6 C15 1.492(6) . ? N1 C7 1.362(6) . ? N1 C8 1.379(6) . ? C5 O1 1.368(5) . ? C5 C9 1.440(6) . ? O2 C7 1.231(5) . ? O1 C4 1.421(6) . ? C9 C10 1.399(6) . ? C9 C8 1.400(6) . ? C13 C12 1.358(7) . ? C13 C8 1.390(7) . ? C15 C20 1.382(7) . ? C15 C16 1.390(7) . ? C10 C11 1.367(7) . ? C20 C19 1.374(7) . ? C11 C12 1.425(7) . ? C11 C14 1.499(7) . ? C16 C17 1.385(7) . ? C18 C17 1.371(8) . ? C18 C19 1.375(8) . ? C18 C21 1.489(9) . ? C4 C3 1.393(8) . ? F1 C21 1.185(10) . ? C21 F2 1.142(9) . ? C21 F3 1.280(10) . ? C1 C2 1.481(10) . ? C3 C2 1.262(9) . ? 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 C5 C6 C7 120.2(4) . . ? C5 C6 C15 123.7(4) . . ? C7 C6 C15 116.0(4) . . ? C7 N1 C8 125.3(4) . . ? C6 C5 O1 122.7(4) . . ? C6 C5 C9 122.1(4) . . ? O1 C5 C9 115.2(4) . . ? C5 O1 C4 118.0(4) . . ? C10 C9 C8 118.3(4) . . ? C10 C9 C5 124.5(4) . . ? C8 C9 C5 117.3(4) . . ? C12 C13 C8 120.0(5) . . ? N1 C8 C13 120.5(4) . . ? N1 C8 C9 119.4(4) . . ? C13 C8 C9 120.1(5) . . ? C20 C15 C16 118.5(4) . . ? C20 C15 C6 121.6(4) . . ? C16 C15 C6 119.9(5) . . ? C11 C10 C9 122.9(4) . . ? O2 C7 N1 120.5(4) . . ? O2 C7 C6 123.9(4) . . ? N1 C7 C6 115.6(5) . . ? C19 C20 C15 120.6(5) . . ? C10 C11 C12 116.8(5) . . ? C10 C11 C14 123.5(5) . . ? C12 C11 C14 119.7(5) . . ? C13 C12 C11 121.9(5) . . ? C17 C16 C15 120.7(5) . . ? C17 C18 C19 119.8(5) . . ? C17 C18 C21 115.9(6) . . ? C19 C18 C21 124.2(7) . . ? C18 C17 C16 119.9(5) . . ? C20 C19 C18 120.5(5) . . ? C3 C4 O1 115.9(6) . . ? F2 C21 F1 108.9(11) . . ? F2 C21 F3 99.3(10) . . ? F1 C21 F3 97.4(10) . . ? F2 C21 C18 119.9(7) . . ? F1 C21 C18 118.1(7) . . ? F3 C21 C18 109.0(9) . . ? C2 C3 C4 136.0(8) . . ? C3 C2 C1 132.2(9) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.490 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 967567' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 N O2' _chemical_formula_weight 321.40 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 7.7051(4) _cell_length_b 10.8189(5) _cell_length_c 11.1726(5) _cell_angle_alpha 75.918(3) _cell_angle_beta 86.590(3) _cell_angle_gamma 87.802(3) _cell_volume 901.49(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _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 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 6207 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3156 _reflns_number_gt 2539 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0891P)^2^+0.1087P] 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 3156 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C6 C 0.3210(2) 0.75886(14) 0.08288(14) 0.0430(4) Uani 1 1 d . . . N1 N 0.20922(17) 0.94569(12) -0.05874(12) 0.0483(4) Uani 1 1 d . . . H1A H 0.1280 1.0023 -0.0795 0.058 Uiso 1 1 calc R . . O2 O 0.05450(15) 0.86660(11) 0.11992(11) 0.0577(4) Uani 1 1 d . . . O1 O 0.59192(14) 0.66825(10) 0.02447(10) 0.0496(3) Uani 1 1 d . . . C5 C 0.4644(2) 0.76206(14) 0.00433(14) 0.0429(4) Uani 1 1 d . . . C7 C 0.1870(2) 0.85939(14) 0.05224(14) 0.0447(4) Uani 1 1 d . . . C9 C 0.4870(2) 0.85904(14) -0.10907(14) 0.0442(4) Uani 1 1 d . . . C8 C 0.3511(2) 0.94930(14) -0.13998(14) 0.0452(4) Uani 1 1 d . . . C15 C 0.29370(19) 0.65651(14) 0.19742(14) 0.0430(4) Uani 1 1 d . . . C10 C 0.6351(2) 0.86664(16) -0.18947(16) 0.0523(4) Uani 1 1 d . . . H10A H 0.7268 0.8085 -0.1680 0.063 Uiso 1 1 calc R . . C13 C 0.3615(2) 1.04028(16) -0.25268(16) 0.0553(4) Uani 1 1 d . . . H13A H 0.2703 1.0986 -0.2751 0.066 Uiso 1 1 calc R . . C16 C 0.3125(2) 0.52897(15) 0.19531(15) 0.0478(4) Uani 1 1 d . . . H16A H 0.3371 0.5067 0.1206 0.057 Uiso 1 1 calc R . . C11 C 0.6486(2) 0.95840(17) -0.30006(17) 0.0580(5) Uani 1 1 d . . . C17 C 0.2950(2) 0.43476(16) 0.30353(16) 0.0561(4) Uani 1 1 d . . . H17A H 0.3090 0.3500 0.2999 0.067 Uiso 1 1 calc R . . C12 C 0.5075(3) 1.04304(17) -0.33041(17) 0.0618(5) Uani 1 1 d . . . H12A H 0.5124 1.1033 -0.4057 0.074 Uiso 1 1 calc R . . C18 C 0.2574(2) 0.46222(18) 0.41660(17) 0.0606(5) Uani 1 1 d . . . C4 C 0.7115(2) 0.67444(17) 0.11734(18) 0.0597(5) Uani 1 1 d . . . H4A H 0.6478 0.6751 0.1947 0.072 Uiso 1 1 calc R . . H4B H 0.7770 0.7521 0.0916 0.072 Uiso 1 1 calc R . . C19 C 0.2348(3) 0.58982(19) 0.41787(17) 0.0663(5) Uani 1 1 d . . . H19A H 0.2076 0.6114 0.4926 0.080 Uiso 1 1 calc R . . C3 C 0.8331(2) 0.56076(19) 0.1345(2) 0.0671(5) Uani 1 1 d . . . H3A H 0.9238 0.5716 0.1874 0.081 Uiso 1 1 calc R . . H3B H 0.8881 0.5578 0.0549 0.081 Uiso 1 1 calc R . . C20 C 0.2517(2) 0.68506(17) 0.31131(15) 0.0564(4) Uani 1 1 d . . . H20A H 0.2349 0.7696 0.3151 0.068 Uiso 1 1 calc R . . C14 C 0.8110(3) 0.9683(2) -0.3838(2) 0.0819(7) Uani 1 1 d . . . H14A H 0.7961 1.0364 -0.4560 0.123 Uiso 1 1 calc R . . H14B H 0.8321 0.8895 -0.4079 0.123 Uiso 1 1 calc R . . H14C H 0.9081 0.9852 -0.3407 0.123 Uiso 1 1 calc R . . C2 C 0.7481(3) 0.43539(19) 0.1899(2) 0.0743(6) Uani 1 1 d . . . H2A H 0.6648 0.4210 0.1331 0.089 Uiso 1 1 calc R . . H2B H 0.6838 0.4414 0.2657 0.089 Uiso 1 1 calc R . . C1 C 0.8711(4) 0.3216(2) 0.2183(3) 0.1075(9) Uani 1 1 d . . . H1B H 0.8063 0.2461 0.2534 0.161 Uiso 1 1 calc R . . H1C H 0.9524 0.3334 0.2762 0.161 Uiso 1 1 calc R . . H1D H 0.9330 0.3127 0.1436 0.161 Uiso 1 1 calc R . . C21 C 0.2446(4) 0.3570(2) 0.5336(2) 0.0935(8) Uani 1 1 d . . . H21A H 0.2637 0.2760 0.5135 0.140 Uiso 1 1 calc R . . H21B H 0.1310 0.3600 0.5732 0.140 Uiso 1 1 calc R . . H21C H 0.3309 0.3682 0.5883 0.140 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 C6 0.0389(8) 0.0394(8) 0.0496(8) -0.0091(6) -0.0045(6) 0.0063(6) N1 0.0395(7) 0.0399(7) 0.0586(8) -0.0015(6) -0.0003(6) 0.0119(5) O2 0.0419(7) 0.0537(7) 0.0662(7) 0.0023(5) 0.0079(5) 0.0142(5) O1 0.0448(7) 0.0478(6) 0.0560(6) -0.0137(5) -0.0072(5) 0.0178(5) C5 0.0391(8) 0.0373(8) 0.0529(8) -0.0126(6) -0.0065(7) 0.0081(6) C7 0.0370(8) 0.0386(8) 0.0558(9) -0.0075(7) -0.0011(7) 0.0038(6) C9 0.0421(9) 0.0380(8) 0.0528(8) -0.0126(7) -0.0015(7) 0.0045(6) C8 0.0410(9) 0.0393(8) 0.0532(8) -0.0082(6) -0.0003(7) 0.0035(6) C15 0.0325(8) 0.0430(8) 0.0512(8) -0.0074(6) -0.0045(6) 0.0049(6) C10 0.0470(10) 0.0475(9) 0.0607(10) -0.0129(7) 0.0036(7) 0.0082(7) C13 0.0566(10) 0.0425(9) 0.0605(10) -0.0022(7) -0.0006(8) 0.0087(7) C16 0.0432(9) 0.0449(9) 0.0550(9) -0.0117(7) -0.0037(7) 0.0039(7) C11 0.0588(11) 0.0503(10) 0.0627(10) -0.0135(8) 0.0123(8) 0.0012(8) C17 0.0516(10) 0.0413(9) 0.0698(11) -0.0027(8) -0.0064(8) 0.0043(7) C12 0.0703(12) 0.0497(10) 0.0580(10) -0.0018(8) 0.0085(9) 0.0018(8) C18 0.0536(10) 0.0601(11) 0.0598(10) 0.0016(8) -0.0067(8) 0.0054(8) C4 0.0409(9) 0.0592(11) 0.0831(12) -0.0243(9) -0.0147(8) 0.0088(8) C19 0.0772(13) 0.0694(12) 0.0495(9) -0.0112(8) -0.0021(9) 0.0081(10) C3 0.0456(10) 0.0681(12) 0.0893(13) -0.0220(10) -0.0156(9) 0.0165(9) C20 0.0627(11) 0.0499(9) 0.0561(10) -0.0131(7) -0.0039(8) 0.0077(8) C14 0.0775(15) 0.0750(13) 0.0828(14) -0.0082(11) 0.0298(12) 0.0043(11) C2 0.0612(12) 0.0665(12) 0.0966(15) -0.0186(11) -0.0284(11) 0.0126(10) C1 0.0937(19) 0.0699(15) 0.160(3) -0.0220(16) -0.0522(18) 0.0222(13) C21 0.1084(19) 0.0830(16) 0.0700(13) 0.0167(11) -0.0027(13) 0.0071(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 C6 C5 1.366(2) . ? C6 C7 1.463(2) . ? C6 C15 1.485(2) . ? N1 C7 1.365(2) . ? N1 C8 1.374(2) . ? O2 C7 1.2454(19) . ? O1 C5 1.3729(17) . ? O1 C4 1.443(2) . ? C5 C9 1.441(2) . ? C9 C8 1.404(2) . ? C9 C10 1.402(2) . ? C8 C13 1.397(2) . ? C15 C16 1.388(2) . ? C15 C20 1.398(2) . ? C10 C11 1.385(2) . ? C13 C12 1.376(2) . ? C16 C17 1.382(2) . ? C11 C12 1.397(3) . ? C11 C14 1.508(3) . ? C17 C18 1.379(3) . ? C18 C19 1.388(3) . ? C18 C21 1.511(3) . ? C4 C3 1.498(2) . ? C19 C20 1.375(2) . ? C3 C2 1.504(3) . ? C2 C1 1.507(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 C5 C6 C7 118.77(14) . . ? C5 C6 C15 122.82(13) . . ? C7 C6 C15 118.40(13) . . ? C7 N1 C8 125.18(13) . . ? C5 O1 C4 115.66(12) . . ? C6 C5 O1 121.99(13) . . ? C6 C5 C9 122.54(14) . . ? O1 C5 C9 115.35(13) . . ? O2 C7 N1 119.79(13) . . ? O2 C7 C6 123.38(14) . . ? N1 C7 C6 116.80(14) . . ? C8 C9 C10 118.97(14) . . ? C8 C9 C5 117.37(14) . . ? C10 C9 C5 123.66(14) . . ? N1 C8 C13 121.20(14) . . ? N1 C8 C9 119.13(14) . . ? C13 C8 C9 119.67(15) . . ? C16 C15 C20 117.71(14) . . ? C16 C15 C6 120.97(14) . . ? C20 C15 C6 121.31(14) . . ? C11 C10 C9 121.79(16) . . ? C12 C13 C8 119.60(16) . . ? C17 C16 C15 120.39(15) . . ? C10 C11 C12 117.64(16) . . ? C10 C11 C14 121.27(18) . . ? C12 C11 C14 121.08(17) . . ? C18 C17 C16 122.25(16) . . ? C13 C12 C11 122.23(16) . . ? C17 C18 C19 117.15(15) . . ? C17 C18 C21 120.84(18) . . ? C19 C18 C21 122.01(19) . . ? O1 C4 C3 108.89(15) . . ? C20 C19 C18 121.55(17) . . ? C4 C3 C2 114.50(17) . . ? C19 C20 C15 120.92(16) . . ? C3 C2 C1 115.0(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.189 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 967568'