# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_sad _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H7 F5 N2 O' _chemical_formula_weight 326.23 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9819(15) _cell_length_b 7.9992(7) _cell_length_c 11.2134(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.480(2) _cell_angle_gamma 90.00 _cell_volume 1317.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 56(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9539 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 56(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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7969 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2993 _reflns_number_gt 2004 _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^)+(0.0755P)^2^+0.1729P] 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 2993 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 C1 C 0.91618(15) 0.1097(3) 0.8792(2) 0.0563(6) Uani 1 1 d . . . C2 C 0.88259(15) 0.1888(3) 0.9697(2) 0.0525(5) Uani 1 1 d . . . C3 C 0.79111(14) 0.1797(3) 0.97020(19) 0.0451(5) Uani 1 1 d . . . C4 C 0.73093(13) 0.0914(2) 0.88333(17) 0.0396(4) Uani 1 1 d . . . C5 C 0.76719(14) 0.0124(3) 0.79336(18) 0.0423(5) Uani 1 1 d . . . C6 C 0.85938(16) 0.0205(3) 0.7921(2) 0.0519(6) Uani 1 1 d . . . C7 C 0.63234(13) 0.0712(2) 0.89560(17) 0.0379(4) Uani 1 1 d . . . C8 C 0.56134(13) 0.0976(2) 0.79513(17) 0.0394(4) Uani 1 1 d . . . C9 C 0.55878(15) 0.1475(3) 0.67461(19) 0.0483(5) Uani 1 1 d . . . H9 H 0.6100 0.1744 0.6401 0.058 Uiso 1 1 calc R . . C10 C 0.46948(15) 0.1506(3) 0.6152(2) 0.0512(5) Uani 1 1 d . . . H10 H 0.4480 0.1799 0.5324 0.061 Uiso 1 1 calc R . . C11 C 0.41527(14) 0.1029(2) 0.69835(18) 0.0412(5) Uani 1 1 d . . . C12 C 0.31754(14) 0.0894(3) 0.67737(18) 0.0436(5) Uani 1 1 d . . . C15 C 0.18033(16) 0.0438(3) 0.7194(2) 0.0615(6) Uani 1 1 d . . . H15 H 0.1336 0.0143 0.7616 0.074 Uiso 1 1 calc R . . C14 C 0.16733(17) 0.1009(3) 0.6037(2) 0.0630(7) Uani 1 1 d . . . H14 H 0.1102 0.1186 0.5507 0.076 Uiso 1 1 calc R . . C13 C 0.25330(16) 0.1294(3) 0.5759(2) 0.0539(6) Uani 1 1 d . . . H13 H 0.2650 0.1690 0.5007 0.065 Uiso 1 1 calc R . . F1 F 1.00536(9) 0.1180(2) 0.87806(16) 0.0855(5) Uani 1 1 d . . . F2 F 0.93871(9) 0.2738(2) 1.05631(15) 0.0790(5) Uani 1 1 d . . . F3 F 0.76167(8) 0.26006(17) 1.06034(12) 0.0579(4) Uani 1 1 d . . . F4 F 0.71431(9) -0.07899(16) 0.70750(11) 0.0557(4) Uani 1 1 d . . . F5 F 0.89228(11) -0.0611(2) 0.70578(14) 0.0755(5) Uani 1 1 d . . . N1 N 0.27150(12) 0.0358(2) 0.76519(16) 0.0507(5) Uani 1 1 d . . . H1 H 0.2969 0.0019 0.8388 0.061 Uiso 1 1 calc R . . N2 N 0.47191(11) 0.0730(2) 0.80601(14) 0.0406(4) Uani 1 1 d . . . H2 H 0.4545 0.0422 0.8732 0.049 Uiso 1 1 calc R . . O1 O 0.61912(10) 0.0319(2) 0.99902(12) 0.0506(4) 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 C1 0.0374(11) 0.0645(14) 0.0719(16) 0.0155(12) 0.0227(11) 0.0050(10) C2 0.0421(11) 0.0550(13) 0.0598(14) 0.0027(11) 0.0085(10) -0.0055(9) C3 0.0464(11) 0.0472(11) 0.0461(11) -0.0001(9) 0.0198(9) -0.0028(9) C4 0.0411(10) 0.0414(10) 0.0400(11) 0.0045(8) 0.0171(9) -0.0013(8) C5 0.0504(12) 0.0435(11) 0.0363(10) 0.0046(9) 0.0163(9) 0.0019(9) C6 0.0584(13) 0.0558(13) 0.0499(13) 0.0103(10) 0.0311(11) 0.0138(10) C7 0.0385(10) 0.0452(11) 0.0323(10) -0.0029(8) 0.0125(8) -0.0046(8) C8 0.0383(10) 0.0447(11) 0.0372(10) 0.0014(8) 0.0122(8) -0.0033(8) C9 0.0513(12) 0.0510(12) 0.0481(12) 0.0112(10) 0.0235(10) 0.0027(9) C10 0.0592(14) 0.0557(13) 0.0427(11) 0.0101(10) 0.0195(10) 0.0060(10) C11 0.0470(11) 0.0415(11) 0.0362(10) -0.0014(8) 0.0109(9) 0.0027(8) C12 0.0454(11) 0.0472(11) 0.0380(11) -0.0061(8) 0.0077(9) 0.0026(8) C15 0.0418(12) 0.0725(16) 0.0715(17) -0.0056(13) 0.0146(11) -0.0002(11) C14 0.0460(13) 0.0740(17) 0.0644(16) -0.0106(13) -0.0001(11) 0.0072(11) C13 0.0570(13) 0.0625(14) 0.0388(11) -0.0047(10) 0.0012(10) 0.0090(10) F1 0.0400(7) 0.1120(13) 0.1113(13) 0.0123(10) 0.0315(8) 0.0054(8) F2 0.0472(8) 0.0954(12) 0.0901(11) -0.0154(9) 0.0034(7) -0.0190(7) F3 0.0553(7) 0.0683(8) 0.0537(8) -0.0199(6) 0.0196(6) -0.0112(6) F4 0.0680(8) 0.0582(8) 0.0445(7) -0.0076(6) 0.0199(6) 0.0013(6) F5 0.0798(10) 0.0873(11) 0.0733(10) 0.0046(8) 0.0487(8) 0.0238(8) N1 0.0422(10) 0.0634(12) 0.0474(11) 0.0033(9) 0.0108(8) -0.0005(8) N2 0.0412(9) 0.0507(10) 0.0328(9) 0.0016(7) 0.0142(7) -0.0030(7) O1 0.0472(8) 0.0737(10) 0.0348(8) -0.0010(7) 0.0175(6) -0.0113(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 C1 F1 1.340(2) . ? C1 C6 1.363(4) . ? C1 C2 1.373(3) . ? C2 F2 1.337(3) . ? C2 C3 1.374(3) . ? C3 F3 1.344(2) . ? C3 C4 1.383(3) . ? C4 C5 1.389(3) . ? C4 C7 1.519(3) . ? C5 F4 1.336(2) . ? C5 C6 1.386(3) . ? C6 F5 1.340(2) . ? C7 O1 1.255(2) . ? C7 C8 1.403(3) . ? C8 N2 1.383(2) . ? C8 C9 1.402(3) . ? C9 C10 1.371(3) . ? C9 H9 0.9500 . ? C10 C11 1.405(3) . ? C10 H10 0.9500 . ? C11 N2 1.352(3) . ? C11 C12 1.440(3) . ? C12 C13 1.374(3) . ? C12 N1 1.378(3) . ? C15 C14 1.353(4) . ? C15 N1 1.362(3) . ? C15 H15 0.9500 . ? C14 C13 1.402(3) . ? C14 H14 0.9500 . ? C13 H13 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? 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 F1 C1 C6 120.0(2) . . ? F1 C1 C2 119.8(2) . . ? C6 C1 C2 120.17(19) . . ? F2 C2 C1 120.1(2) . . ? F2 C2 C3 120.5(2) . . ? C1 C2 C3 119.4(2) . . ? F3 C3 C2 117.06(19) . . ? F3 C3 C4 120.58(17) . . ? C2 C3 C4 122.36(19) . . ? C3 C4 C5 116.72(18) . . ? C3 C4 C7 119.99(16) . . ? C5 C4 C7 123.04(18) . . ? F4 C5 C6 117.86(18) . . ? F4 C5 C4 120.70(18) . . ? C6 C5 C4 121.4(2) . . ? F5 C6 C1 120.4(2) . . ? F5 C6 C5 119.7(2) . . ? C1 C6 C5 119.89(19) . . ? O1 C7 C8 123.10(17) . . ? O1 C7 C4 116.45(17) . . ? C8 C7 C4 120.45(16) . . ? N2 C8 C9 106.52(17) . . ? N2 C8 C7 120.03(16) . . ? C9 C8 C7 133.45(18) . . ? C10 C9 C8 108.06(17) . . ? C10 C9 H9 126.0 . . ? C8 C9 H9 126.0 . . ? C9 C10 C11 108.06(19) . . ? C9 C10 H10 126.0 . . ? C11 C10 H10 126.0 . . ? N2 C11 C10 107.31(18) . . ? N2 C11 C12 124.73(17) . . ? C10 C11 C12 128.0(2) . . ? C13 C12 N1 107.24(19) . . ? C13 C12 C11 129.8(2) . . ? N1 C12 C11 122.94(19) . . ? C14 C15 N1 108.7(2) . . ? C14 C15 H15 125.7 . . ? N1 C15 H15 125.7 . . ? C15 C14 C13 107.7(2) . . ? C15 C14 H14 126.1 . . ? C13 C14 H14 126.1 . . ? C12 C13 C14 107.6(2) . . ? C12 C13 H13 126.2 . . ? C14 C13 H13 126.2 . . ? C15 N1 C12 108.8(2) . . ? C15 N1 H1 125.6 . . ? C12 N1 H1 125.6 . . ? C11 N2 C8 110.05(16) . . ? C11 N2 H2 125.0 . . ? C8 N2 H2 125.0 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.170 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 954442' ####################################################################### # # 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_130110f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H6 F10 N2 O2' _chemical_formula_weight 520.29 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9337(8) _cell_length_b 9.6006(6) _cell_length_c 17.6397(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.1080(10) _cell_angle_gamma 90.00 _cell_volume 2015.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1057 _cell_measurement_theta_min 2.7202 _cell_measurement_theta_max 28.3355 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9337 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details sadabs _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 '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 7680 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3548 _reflns_number_gt 2086 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _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^)+(0.0301P)^2^+0.0154P] 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 3548 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.29621(14) 0.56913(16) 0.15438(10) 0.0593(5) Uani 1 1 d . . . F2 F 0.21177(16) 0.49118(19) 0.01598(11) 0.0752(6) Uani 1 1 d . . . F3 F 0.04050(17) 0.6324(2) -0.05510(11) 0.0826(6) Uani 1 1 d . . . F4 F -0.04544(16) 0.8598(2) 0.01149(12) 0.0893(7) Uani 1 1 d . . . F5 F 0.04481(16) 0.94707(19) 0.14715(11) 0.0782(6) Uani 1 1 d . . . F6 F 0.47719(15) 0.8091(2) 0.75625(11) 0.0816(6) Uani 1 1 d . . . F7 F 0.60508(18) 0.7463(2) 0.88289(11) 0.0845(6) Uani 1 1 d . . . F8 F 0.82965(18) 0.7209(2) 0.87804(12) 0.0970(8) Uani 1 1 d . . . F9 F 0.92575(16) 0.7510(2) 0.74538(14) 0.1066(8) Uani 1 1 d . . . F10 F 0.79770(16) 0.8074(2) 0.61717(12) 0.0837(6) Uani 1 1 d . . . N1 N 0.29785(18) 0.7736(2) 0.35941(13) 0.0407(6) Uani 1 1 d . . . H1 H 0.3334 0.8514 0.3639 0.049 Uiso 1 1 calc R . . N2 N 0.43032(18) 0.7882(2) 0.50805(13) 0.0407(6) Uani 1 1 d . . . H2 H 0.4339 0.8662 0.4843 0.049 Uiso 1 1 calc R . . O1 O 0.2700(2) 0.9332(2) 0.22784(12) 0.0696(7) Uani 1 1 d . . . O2 O 0.57788(17) 0.9735(2) 0.58944(12) 0.0591(6) Uani 1 1 d . . . C1 C 0.2330(2) 0.7326(3) 0.29626(16) 0.0395(7) Uani 1 1 d . . . C2 C 0.1876(2) 0.6051(3) 0.31233(18) 0.0513(8) Uani 1 1 d . . . H2A H 0.1391 0.5529 0.2800 0.062 Uiso 1 1 calc R . . C3 C 0.2277(3) 0.5685(3) 0.38577(17) 0.0532(9) Uani 1 1 d . . . H3 H 0.2102 0.4876 0.4114 0.064 Uiso 1 1 calc R . . C4 C 0.2979(2) 0.6738(3) 0.41384(16) 0.0405(7) Uani 1 1 d . . . C5 C 0.3648(2) 0.6788(3) 0.48469(16) 0.0399(7) Uani 1 1 d . . . C6 C 0.3815(3) 0.5750(3) 0.53895(17) 0.0518(8) Uani 1 1 d . . . H6 H 0.3462 0.4886 0.5379 0.062 Uiso 1 1 calc R . . C7 C 0.4596(2) 0.6217(3) 0.59479(17) 0.0493(8) Uani 1 1 d . . . H7 H 0.4867 0.5723 0.6376 0.059 Uiso 1 1 calc R . . C8 C 0.4904(2) 0.7560(3) 0.57541(15) 0.0406(7) Uani 1 1 d . . . C9 C 0.2278(2) 0.8175(3) 0.22856(17) 0.0447(8) Uani 1 1 d . . . C10 C 0.1720(2) 0.7596(3) 0.15623(16) 0.0404(7) Uani 1 1 d . . . C11 C 0.2110(2) 0.6428(3) 0.12067(17) 0.0424(7) Uani 1 1 d . . . C12 C 0.1679(3) 0.6011(3) 0.05003(18) 0.0491(8) Uani 1 1 d . . . C13 C 0.0824(3) 0.6742(3) 0.01357(18) 0.0544(9) Uani 1 1 d . . . C14 C 0.0404(3) 0.7897(3) 0.04679(19) 0.0569(9) Uani 1 1 d . . . C15 C 0.0861(3) 0.8320(3) 0.11629(18) 0.0519(8) Uani 1 1 d . . . C16 C 0.5647(2) 0.8532(3) 0.61261(16) 0.0410(7) Uani 1 1 d . . . C17 C 0.6333(2) 0.8070(3) 0.68271(16) 0.0388(7) Uani 1 1 d . . . C18 C 0.5881(2) 0.7898(3) 0.75126(18) 0.0468(8) Uani 1 1 d . . . C19 C 0.6525(3) 0.7598(3) 0.81675(18) 0.0518(8) Uani 1 1 d . . . C20 C 0.7658(3) 0.7470(3) 0.8143(2) 0.0577(9) Uani 1 1 d . . . C21 C 0.8136(3) 0.7627(3) 0.7472(2) 0.0591(9) Uani 1 1 d . . . C22 C 0.7477(3) 0.7922(3) 0.68269(19) 0.0500(8) 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 F1 0.0602(11) 0.0561(11) 0.0595(13) -0.0066(9) -0.0118(10) 0.0106(8) F2 0.0977(15) 0.0678(13) 0.0597(14) -0.0232(10) 0.0038(12) 0.0019(11) F3 0.0895(15) 0.1086(15) 0.0459(13) -0.0121(11) -0.0223(12) -0.0161(12) F4 0.0756(14) 0.1118(16) 0.0751(15) 0.0072(13) -0.0315(13) 0.0252(12) F5 0.0868(14) 0.0741(13) 0.0721(15) -0.0084(11) -0.0060(12) 0.0345(11) F6 0.0461(12) 0.1446(18) 0.0545(13) 0.0111(12) 0.0062(10) 0.0016(11) F7 0.0991(16) 0.1168(17) 0.0372(12) 0.0132(11) 0.0016(12) -0.0128(13) F8 0.0925(16) 0.1131(17) 0.0777(16) 0.0296(13) -0.0476(14) -0.0031(12) F9 0.0451(12) 0.151(2) 0.122(2) 0.0148(16) -0.0078(14) 0.0228(12) F10 0.0645(13) 0.1203(16) 0.0691(15) 0.0125(12) 0.0233(12) 0.0103(11) N1 0.0449(14) 0.0380(13) 0.0383(15) -0.0024(12) -0.0025(12) -0.0062(10) N2 0.0480(14) 0.0397(13) 0.0335(14) 0.0044(11) -0.0031(12) -0.0061(11) O1 0.1097(19) 0.0433(13) 0.0527(15) -0.0020(11) -0.0147(14) -0.0162(12) O2 0.0709(15) 0.0527(13) 0.0506(15) 0.0139(11) -0.0173(12) -0.0154(11) C1 0.0402(16) 0.0441(17) 0.0341(18) -0.0055(14) 0.0006(14) -0.0036(13) C2 0.0525(19) 0.057(2) 0.044(2) -0.0063(16) -0.0028(17) -0.0171(15) C3 0.065(2) 0.0519(19) 0.041(2) 0.0025(16) -0.0032(18) -0.0195(16) C4 0.0442(17) 0.0433(17) 0.0340(18) -0.0015(14) 0.0023(15) -0.0015(13) C5 0.0470(18) 0.0407(17) 0.0321(17) -0.0019(14) 0.0028(15) -0.0017(13) C6 0.065(2) 0.0447(18) 0.045(2) 0.0025(16) -0.0034(18) -0.0096(15) C7 0.063(2) 0.0423(18) 0.041(2) 0.0078(15) -0.0038(17) 0.0018(14) C8 0.0490(18) 0.0415(17) 0.0303(17) 0.0026(14) -0.0040(15) 0.0010(14) C9 0.0517(19) 0.0424(18) 0.0396(19) -0.0074(15) -0.0003(16) 0.0016(14) C10 0.0433(17) 0.0418(17) 0.0356(18) -0.0011(14) -0.0006(15) -0.0030(13) C11 0.0410(17) 0.0443(18) 0.0410(19) 0.0034(15) -0.0027(15) -0.0006(13) C12 0.056(2) 0.049(2) 0.042(2) -0.0093(16) 0.0028(18) -0.0071(15) C13 0.059(2) 0.071(2) 0.0317(19) -0.0030(17) -0.0084(17) -0.0174(18) C14 0.050(2) 0.073(2) 0.046(2) 0.0051(19) -0.0105(18) 0.0027(17) C15 0.058(2) 0.052(2) 0.046(2) -0.0032(16) 0.0003(18) 0.0092(16) C16 0.0451(18) 0.0446(18) 0.0328(18) 0.0054(14) -0.0004(15) 0.0011(14) C17 0.0424(18) 0.0395(16) 0.0335(18) 0.0049(14) -0.0033(15) -0.0053(13) C18 0.0415(19) 0.058(2) 0.040(2) 0.0059(16) -0.0069(16) -0.0038(14) C19 0.063(2) 0.056(2) 0.0350(19) 0.0076(16) -0.0014(18) -0.0089(16) C20 0.058(2) 0.056(2) 0.055(2) 0.0126(18) -0.027(2) -0.0026(16) C21 0.042(2) 0.061(2) 0.074(3) 0.0075(19) -0.004(2) 0.0082(15) C22 0.049(2) 0.057(2) 0.044(2) 0.0061(16) 0.0044(17) 0.0028(15) _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 C11 1.342(3) . ? F2 C12 1.339(3) . ? F3 C13 1.338(3) . ? F4 C14 1.341(3) . ? F5 C15 1.341(3) . ? F6 C18 1.346(3) . ? F7 C19 1.339(3) . ? F8 C20 1.335(3) . ? F9 C21 1.346(3) . ? F10 C22 1.346(3) . ? N1 C4 1.356(3) . ? N1 C1 1.368(3) . ? N1 H1 0.8600 . ? N2 C5 1.355(3) . ? N2 C8 1.378(3) . ? N2 H2 0.8600 . ? O1 C9 1.221(3) . ? O2 C16 1.239(3) . ? C1 C2 1.376(4) . ? C1 C9 1.443(4) . ? C2 C3 1.393(4) . ? C2 H2A 0.9300 . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.435(4) . ? C5 C6 1.387(4) . ? C6 C7 1.382(4) . ? C6 H6 0.9300 . ? C7 C8 1.389(3) . ? C7 H7 0.9300 . ? C8 C16 1.416(4) . ? C9 C10 1.503(4) . ? C10 C11 1.382(4) . ? C10 C15 1.388(4) . ? C11 C12 1.373(4) . ? C12 C13 1.362(4) . ? C13 C14 1.366(4) . ? C14 C15 1.368(4) . ? C16 C17 1.500(4) . ? C17 C18 1.368(4) . ? C17 C22 1.373(4) . ? C18 C19 1.372(4) . ? C19 C20 1.361(4) . ? C20 C21 1.360(4) . ? C21 C22 1.365(4) . ? 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 C4 N1 C1 110.2(2) . . ? C4 N1 H1 124.9 . . ? C1 N1 H1 124.9 . . ? C5 N2 C8 110.0(2) . . ? C5 N2 H2 125.0 . . ? C8 N2 H2 125.0 . . ? N1 C1 C2 107.2(2) . . ? N1 C1 C9 120.0(2) . . ? C2 C1 C9 132.7(3) . . ? C1 C2 C3 107.6(3) . . ? C1 C2 H2A 126.2 . . ? C3 C2 H2A 126.2 . . ? C4 C3 C2 107.9(3) . . ? C4 C3 H3 126.0 . . ? C2 C3 H3 126.0 . . ? N1 C4 C3 107.1(3) . . ? N1 C4 C5 124.4(2) . . ? C3 C4 C5 128.4(3) . . ? N2 C5 C6 107.2(3) . . ? N2 C5 C4 124.3(2) . . ? C6 C5 C4 128.4(3) . . ? C7 C6 C5 108.3(3) . . ? C7 C6 H6 125.8 . . ? C5 C6 H6 125.8 . . ? C6 C7 C8 107.6(3) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? N2 C8 C7 106.9(2) . . ? N2 C8 C16 121.4(2) . . ? C7 C8 C16 131.7(3) . . ? O1 C9 C1 121.9(3) . . ? O1 C9 C10 119.1(3) . . ? C1 C9 C10 119.0(3) . . ? C11 C10 C15 115.9(3) . . ? C11 C10 C9 122.9(2) . . ? C15 C10 C9 120.8(3) . . ? F1 C11 C12 118.1(3) . . ? F1 C11 C10 119.7(3) . . ? C12 C11 C10 122.1(3) . . ? F2 C12 C13 119.9(3) . . ? F2 C12 C11 120.2(3) . . ? C13 C12 C11 119.9(3) . . ? F3 C13 C12 119.5(3) . . ? F3 C13 C14 120.5(3) . . ? C12 C13 C14 120.1(3) . . ? F4 C14 C13 120.0(3) . . ? F4 C14 C15 120.6(3) . . ? C13 C14 C15 119.4(3) . . ? F5 C15 C14 118.3(3) . . ? F5 C15 C10 119.1(3) . . ? C14 C15 C10 122.6(3) . . ? O2 C16 C8 123.5(3) . . ? O2 C16 C17 118.3(2) . . ? C8 C16 C17 118.2(2) . . ? C18 C17 C22 116.2(3) . . ? C18 C17 C16 122.6(2) . . ? C22 C17 C16 120.9(3) . . ? F6 C18 C17 119.5(3) . . ? F6 C18 C19 117.9(3) . . ? C17 C18 C19 122.5(3) . . ? F7 C19 C20 120.1(3) . . ? F7 C19 C18 120.5(3) . . ? C20 C19 C18 119.4(3) . . ? F8 C20 C21 120.3(3) . . ? F8 C20 C19 119.9(3) . . ? C21 C20 C19 119.8(3) . . ? F9 C21 C20 119.4(3) . . ? F9 C21 C22 120.8(3) . . ? C20 C21 C22 119.8(3) . . ? F10 C22 C21 118.3(3) . . ? F10 C22 C17 119.4(3) . . ? C21 C22 C17 122.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 2.1(3) . . . . ? C4 N1 C1 C9 -175.0(2) . . . . ? N1 C1 C2 C3 -1.0(3) . . . . ? C9 C1 C2 C3 175.5(3) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C1 N1 C4 C3 -2.3(3) . . . . ? C1 N1 C4 C5 174.7(2) . . . . ? C2 C3 C4 N1 1.7(3) . . . . ? C2 C3 C4 C5 -175.2(3) . . . . ? C8 N2 C5 C6 1.1(3) . . . . ? C8 N2 C5 C4 -175.2(3) . . . . ? N1 C4 C5 N2 4.7(4) . . . . ? C3 C4 C5 N2 -178.9(3) . . . . ? N1 C4 C5 C6 -170.8(3) . . . . ? C3 C4 C5 C6 5.6(5) . . . . ? N2 C5 C6 C7 -1.1(3) . . . . ? C4 C5 C6 C7 175.0(3) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C5 N2 C8 C7 -0.7(3) . . . . ? C5 N2 C8 C16 -179.3(3) . . . . ? C6 C7 C8 N2 0.0(3) . . . . ? C6 C7 C8 C16 178.4(3) . . . . ? N1 C1 C9 O1 -8.0(4) . . . . ? C2 C1 C9 O1 175.8(3) . . . . ? N1 C1 C9 C10 169.9(2) . . . . ? C2 C1 C9 C10 -6.3(5) . . . . ? O1 C9 C10 C11 115.7(3) . . . . ? C1 C9 C10 C11 -62.3(4) . . . . ? O1 C9 C10 C15 -56.0(4) . . . . ? C1 C9 C10 C15 126.0(3) . . . . ? C15 C10 C11 F1 178.0(2) . . . . ? C9 C10 C11 F1 6.0(4) . . . . ? C15 C10 C11 C12 0.3(4) . . . . ? C9 C10 C11 C12 -171.8(3) . . . . ? F1 C11 C12 F2 -1.1(4) . . . . ? C10 C11 C12 F2 176.8(3) . . . . ? F1 C11 C12 C13 -179.2(3) . . . . ? C10 C11 C12 C13 -1.4(4) . . . . ? F2 C12 C13 F3 2.2(4) . . . . ? C11 C12 C13 F3 -179.7(3) . . . . ? F2 C12 C13 C14 -177.4(3) . . . . ? C11 C12 C13 C14 0.8(5) . . . . ? F3 C13 C14 F4 1.9(5) . . . . ? C12 C13 C14 F4 -178.6(3) . . . . ? F3 C13 C14 C15 -178.6(3) . . . . ? C12 C13 C14 C15 0.9(5) . . . . ? F4 C14 C15 F5 -1.7(5) . . . . ? C13 C14 C15 F5 178.9(3) . . . . ? F4 C14 C15 C10 177.4(3) . . . . ? C13 C14 C15 C10 -2.1(5) . . . . ? C11 C10 C15 F5 -179.5(3) . . . . ? C9 C10 C15 F5 -7.3(4) . . . . ? C11 C10 C15 C14 1.5(4) . . . . ? C9 C10 C15 C14 173.7(3) . . . . ? N2 C8 C16 O2 2.7(4) . . . . ? C7 C8 C16 O2 -175.5(3) . . . . ? N2 C8 C16 C17 -175.7(2) . . . . ? C7 C8 C16 C17 6.0(5) . . . . ? O2 C16 C17 C18 106.9(3) . . . . ? C8 C16 C17 C18 -74.6(4) . . . . ? O2 C16 C17 C22 -66.9(4) . . . . ? C8 C16 C17 C22 111.6(3) . . . . ? C22 C17 C18 F6 177.0(2) . . . . ? C16 C17 C18 F6 2.9(4) . . . . ? C22 C17 C18 C19 0.1(4) . . . . ? C16 C17 C18 C19 -174.0(3) . . . . ? F6 C18 C19 F7 1.9(4) . . . . ? C17 C18 C19 F7 178.8(3) . . . . ? F6 C18 C19 C20 -176.6(3) . . . . ? C17 C18 C19 C20 0.4(5) . . . . ? F7 C19 C20 F8 0.0(4) . . . . ? C18 C19 C20 F8 178.5(3) . . . . ? F7 C19 C20 C21 -179.1(3) . . . . ? C18 C19 C20 C21 -0.6(5) . . . . ? F8 C20 C21 F9 0.3(5) . . . . ? C19 C20 C21 F9 179.4(3) . . . . ? F8 C20 C21 C22 -178.6(3) . . . . ? C19 C20 C21 C22 0.5(5) . . . . ? F9 C21 C22 F10 0.9(5) . . . . ? C20 C21 C22 F10 179.9(3) . . . . ? F9 C21 C22 C17 -179.0(3) . . . . ? C20 C21 C22 C17 0.0(5) . . . . ? C18 C17 C22 F10 179.9(2) . . . . ? C16 C17 C22 F10 -6.0(4) . . . . ? C18 C17 C22 C21 -0.3(4) . . . . ? C16 C17 C22 C21 173.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 954443' ####################################################################### # # 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_130403b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H9 F10 N3 O' _chemical_formula_weight 569.36 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' O O 0.0106 0.0060 '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' 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.3922(11) _cell_length_b 9.0079(10) _cell_length_c 20.4967(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.2440(10) _cell_angle_gamma 90.00 _cell_volume 2286.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1055 _cell_measurement_theta_min 3.7320 _cell_measurement_theta_max 20.4820 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9274 _exptl_absorpt_correction_T_max 0.9597 _exptl_absorpt_process_details sadabs _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 '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 8012 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4039 _reflns_number_gt 2047 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0259P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4039 _refine_ls_number_parameters 362 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.034 _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 0.3131(2) 0.9543(3) 0.84849(10) 0.0818(8) Uani 1 1 d . . . F2 F 0.1539(2) 1.0114(3) 0.93120(10) 0.0879(8) Uani 1 1 d . . . F3 F -0.0153(2) 0.8268(3) 0.93688(10) 0.0981(10) Uani 1 1 d U . . F4 F -0.02792(19) 0.5823(3) 0.85867(10) 0.0857(8) Uani 1 1 d . . . F5 F 0.12906(18) 0.5273(3) 0.77487(10) 0.0746(7) Uani 1 1 d . . . F6 F 0.86663(18) 0.7980(3) 0.45532(9) 0.0741(7) Uani 1 1 d . . . F7 F 0.9505(2) 0.8729(3) 0.34208(10) 0.0854(8) Uani 1 1 d . . . F8 F 0.8380(2) 0.8252(3) 0.22801(10) 0.0909(9) Uani 1 1 d . . . F9 F 0.6405(2) 0.6986(3) 0.22896(9) 0.0909(9) Uani 1 1 d . . . F10 F 0.55845(18) 0.6076(3) 0.34148(8) 0.0669(7) Uani 1 1 d . . . N1 N 0.3923(2) 0.7255(3) 0.65812(12) 0.0499(8) Uani 1 1 d . . . H1 H 0.4510 0.6775 0.6674 0.060 Uiso 1 1 calc R . . N2 N 0.5229(2) 0.6970(3) 0.54497(12) 0.0474(8) Uani 1 1 d . . . N3 N 0.6902(3) 0.4997(3) 0.56448(12) 0.0552(9) Uani 1 1 d . . . H3 H 0.6343 0.5302 0.5842 0.066 Uiso 1 1 calc R . . O1 O 0.3931(2) 0.6313(3) 0.79171(11) 0.0715(9) Uani 1 1 d . . . C1 C 0.3119(3) 0.7519(4) 0.70087(15) 0.0465(10) Uani 1 1 d . . . C2 C 0.2326(3) 0.8305(4) 0.66734(16) 0.0551(11) Uani 1 1 d . . . H2 H 0.1679 0.8629 0.6840 0.066 Uiso 1 1 calc R . . C3 C 0.2656(3) 0.8531(4) 0.60441(17) 0.0574(11) Uani 1 1 d . . . H3A H 0.2274 0.9042 0.5715 0.069 Uiso 1 1 calc R . . C4 C 0.3655(3) 0.7862(4) 0.59905(16) 0.0462(9) Uani 1 1 d . . . C5 C 0.4337(3) 0.7769(4) 0.54392(15) 0.0450(9) Uani 1 1 d . . . C6 C 0.4161(3) 0.8561(4) 0.48317(15) 0.0529(10) Uani 1 1 d . . . H6 H 0.3579 0.9172 0.4717 0.063 Uiso 1 1 calc R . . C7 C 0.5002(3) 0.8240(4) 0.44678(15) 0.0503(10) Uani 1 1 d . . . H7 H 0.5123 0.8600 0.4052 0.060 Uiso 1 1 calc R . . C8 C 0.5688(3) 0.7231(4) 0.48399(15) 0.0448(9) Uani 1 1 d . . . C9 C 0.6629(3) 0.6563(4) 0.46680(14) 0.0440(9) Uani 1 1 d . . . C10 C 0.7223(3) 0.5497(4) 0.50485(15) 0.0472(10) Uani 1 1 d . . . C11 C 0.8152(3) 0.4710(4) 0.49156(17) 0.0602(11) Uani 1 1 d . . . H11 H 0.8550 0.4806 0.4543 0.072 Uiso 1 1 calc R . . C12 C 0.8387(3) 0.3750(5) 0.54360(17) 0.0628(12) Uani 1 1 d . . . H12 H 0.8968 0.3099 0.5477 0.075 Uiso 1 1 calc R . . C13 C 0.7600(3) 0.3951(5) 0.58733(17) 0.0611(11) Uani 1 1 d . . . H13 H 0.7552 0.3447 0.6267 0.073 Uiso 1 1 calc R . . C14 C 0.3177(3) 0.7025(4) 0.76711(16) 0.0516(10) Uani 1 1 d . . . C15 C 0.2240(3) 0.7390(4) 0.80898(15) 0.0469(10) Uani 1 1 d . . . C16 C 0.2283(3) 0.8609(5) 0.84977(17) 0.0563(11) Uani 1 1 d . . . C17 C 0.1483(4) 0.8911(5) 0.89256(17) 0.0588(11) Uani 1 1 d . . . C18 C 0.0633(3) 0.7981(5) 0.89485(16) 0.0568(11) Uani 1 1 d U . . C19 C 0.0558(3) 0.6752(5) 0.85592(17) 0.0557(11) Uani 1 1 d . . . C20 C 0.1361(3) 0.6493(5) 0.81295(16) 0.0505(10) Uani 1 1 d . . . C21 C 0.7101(3) 0.6974(4) 0.40327(15) 0.0454(9) Uani 1 1 d . . . C22 C 0.8094(3) 0.7643(4) 0.39986(16) 0.0519(10) Uani 1 1 d . . . C23 C 0.8538(3) 0.8054(4) 0.34237(18) 0.0551(11) Uani 1 1 d . . . C24 C 0.7964(4) 0.7820(5) 0.28485(17) 0.0592(12) Uani 1 1 d . . . C25 C 0.6973(3) 0.7171(5) 0.28554(16) 0.0585(11) Uani 1 1 d . . . C26 C 0.6555(3) 0.6739(4) 0.34381(16) 0.0489(10) 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 F1 0.0678(18) 0.0838(18) 0.0949(16) -0.0172(14) 0.0154(13) -0.0228(16) F2 0.084(2) 0.091(2) 0.0888(16) -0.0347(14) 0.0083(14) 0.0068(16) F3 0.0588(18) 0.161(3) 0.0761(15) -0.0135(16) 0.0214(12) 0.0148(18) F4 0.0513(16) 0.122(2) 0.0849(15) -0.0041(14) 0.0214(12) -0.0278(17) F5 0.0637(17) 0.0826(18) 0.0785(15) -0.0219(13) 0.0146(12) -0.0155(14) F6 0.0620(16) 0.104(2) 0.0557(13) -0.0016(12) -0.0053(11) -0.0207(15) F7 0.0649(18) 0.104(2) 0.0892(16) 0.0014(14) 0.0227(13) -0.0285(17) F8 0.105(2) 0.114(2) 0.0565(13) 0.0081(13) 0.0328(13) -0.0164(18) F9 0.097(2) 0.133(2) 0.0423(13) -0.0093(12) -0.0005(12) -0.0230(18) F10 0.0591(16) 0.0817(17) 0.0601(13) -0.0120(11) 0.0050(10) -0.0181(14) N1 0.0359(19) 0.063(2) 0.0517(18) 0.0036(16) 0.0105(14) 0.0056(17) N2 0.041(2) 0.058(2) 0.0438(17) -0.0005(14) 0.0118(13) 0.0000(18) N3 0.053(2) 0.071(2) 0.0433(18) 0.0027(16) 0.0127(15) 0.004(2) O1 0.0459(19) 0.106(2) 0.0636(16) 0.0125(15) 0.0060(13) 0.0129(18) C1 0.031(2) 0.062(3) 0.047(2) -0.0006(19) 0.0082(16) 0.001(2) C2 0.051(3) 0.061(3) 0.055(2) -0.007(2) 0.0128(19) 0.011(2) C3 0.050(3) 0.067(3) 0.056(2) 0.004(2) 0.0039(19) 0.012(2) C4 0.041(3) 0.047(2) 0.050(2) -0.0018(18) 0.0062(17) -0.001(2) C5 0.040(2) 0.050(2) 0.045(2) -0.0050(18) 0.0033(17) 0.000(2) C6 0.053(3) 0.057(3) 0.049(2) -0.0019(19) 0.0013(18) 0.005(2) C7 0.050(3) 0.059(3) 0.043(2) 0.0017(18) 0.0043(18) 0.001(2) C8 0.042(2) 0.052(2) 0.041(2) -0.0029(17) 0.0051(17) -0.002(2) C9 0.046(2) 0.048(2) 0.0385(19) -0.0025(17) 0.0055(17) -0.004(2) C10 0.049(3) 0.051(3) 0.042(2) -0.0072(18) 0.0078(18) -0.003(2) C11 0.063(3) 0.066(3) 0.052(2) -0.002(2) 0.016(2) 0.006(3) C12 0.057(3) 0.065(3) 0.067(3) 0.000(2) 0.011(2) 0.016(2) C13 0.063(3) 0.070(3) 0.050(2) 0.004(2) -0.001(2) 0.007(3) C14 0.035(2) 0.066(3) 0.054(2) 0.002(2) 0.0058(18) -0.003(2) C15 0.037(2) 0.062(3) 0.042(2) -0.0005(19) 0.0055(16) 0.000(2) C16 0.042(3) 0.070(3) 0.057(2) 0.003(2) 0.0039(19) -0.008(2) C17 0.056(3) 0.064(3) 0.056(2) -0.012(2) 0.002(2) 0.007(3) C18 0.045(3) 0.085(3) 0.041(2) 0.001(2) 0.0080(16) 0.013(3) C19 0.034(2) 0.079(3) 0.054(2) 0.003(2) 0.0062(18) -0.011(2) C20 0.040(3) 0.066(3) 0.046(2) -0.008(2) 0.0057(17) -0.001(2) C21 0.051(3) 0.049(2) 0.037(2) -0.0047(17) 0.0086(17) 0.002(2) C22 0.051(3) 0.063(3) 0.042(2) -0.0028(19) 0.0057(19) -0.002(2) C23 0.044(3) 0.060(3) 0.063(3) -0.006(2) 0.013(2) -0.007(2) C24 0.074(3) 0.065(3) 0.040(2) -0.001(2) 0.024(2) -0.007(3) C25 0.069(3) 0.073(3) 0.034(2) -0.0080(19) 0.003(2) -0.005(3) C26 0.046(3) 0.057(3) 0.044(2) -0.0071(18) 0.0080(18) -0.008(2) _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 C16 1.347(4) . ? F2 C17 1.342(4) . ? F3 C18 1.350(4) . ? F4 C19 1.336(4) . ? F5 C20 1.349(4) . ? F6 C22 1.350(4) . ? F7 C23 1.344(4) . ? F8 C24 1.349(4) . ? F9 C25 1.343(4) . ? F10 C26 1.341(4) . ? N1 C4 1.358(4) . ? N1 C1 1.373(4) . ? N1 H1 0.8600 . ? N2 C5 1.319(4) . ? N2 C8 1.413(4) . ? N3 C13 1.351(4) . ? N3 C10 1.376(4) . ? N3 H3 0.8600 . ? O1 C14 1.225(4) . ? C1 C2 1.374(5) . ? C1 C14 1.428(4) . ? C2 C3 1.383(4) . ? C2 H2 0.9300 . ? C3 C4 1.386(5) . ? C3 H3A 0.9300 . ? C4 C5 1.439(4) . ? C5 C6 1.444(4) . ? C6 C7 1.337(5) . ? C6 H6 0.9300 . ? C7 C8 1.441(5) . ? C7 H7 0.9300 . ? C8 C9 1.371(5) . ? C9 C10 1.423(5) . ? C9 C21 1.495(4) . ? C10 C11 1.388(5) . ? C11 C12 1.395(5) . ? C11 H11 0.9300 . ? C12 C13 1.362(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.508(5) . ? C15 C20 1.361(5) . ? C15 C16 1.380(5) . ? C16 C17 1.376(5) . ? C17 C18 1.348(5) . ? C18 C19 1.366(5) . ? C19 C20 1.374(5) . ? C21 C22 1.375(5) . ? C21 C26 1.387(4) . ? C22 C23 1.370(5) . ? C23 C24 1.369(5) . ? C24 C25 1.360(5) . ? C25 C26 1.377(5) . ? 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 C4 N1 C1 109.9(3) . . ? C4 N1 H1 125.0 . . ? C1 N1 H1 125.0 . . ? C5 N2 C8 105.1(3) . . ? C13 N3 C10 109.5(3) . . ? C13 N3 H3 125.3 . . ? C10 N3 H3 125.3 . . ? N1 C1 C2 107.1(3) . . ? N1 C1 C14 122.8(3) . . ? C2 C1 C14 130.1(3) . . ? C1 C2 C3 108.1(3) . . ? C1 C2 H2 126.0 . . ? C3 C2 H2 126.0 . . ? C2 C3 C4 107.9(3) . . ? C2 C3 H3A 126.0 . . ? C4 C3 H3A 126.0 . . ? N1 C4 C3 107.0(3) . . ? N1 C4 C5 123.1(3) . . ? C3 C4 C5 129.9(3) . . ? N2 C5 C4 122.4(3) . . ? N2 C5 C6 112.4(3) . . ? C4 C5 C6 125.1(4) . . ? C7 C6 C5 106.2(3) . . ? C7 C6 H6 126.9 . . ? C5 C6 H6 126.9 . . ? C6 C7 C8 107.3(3) . . ? C6 C7 H7 126.4 . . ? C8 C7 H7 126.4 . . ? C9 C8 N2 122.0(3) . . ? C9 C8 C7 129.1(3) . . ? N2 C8 C7 108.9(3) . . ? C8 C9 C10 125.6(3) . . ? C8 C9 C21 118.7(3) . . ? C10 C9 C21 115.7(3) . . ? N3 C10 C11 106.1(3) . . ? N3 C10 C9 123.2(3) . . ? C11 C10 C9 130.7(3) . . ? C10 C11 C12 108.5(3) . . ? C10 C11 H11 125.8 . . ? C12 C11 H11 125.8 . . ? C13 C12 C11 106.7(4) . . ? C13 C12 H12 126.6 . . ? C11 C12 H12 126.6 . . ? N3 C13 C12 109.3(3) . . ? N3 C13 H13 125.4 . . ? C12 C13 H13 125.4 . . ? O1 C14 C1 124.3(3) . . ? O1 C14 C15 118.2(3) . . ? C1 C14 C15 117.5(3) . . ? C20 C15 C16 116.6(3) . . ? C20 C15 C14 122.8(3) . . ? C16 C15 C14 120.4(4) . . ? F1 C16 C17 118.1(4) . . ? F1 C16 C15 119.8(3) . . ? C17 C16 C15 122.1(4) . . ? F2 C17 C18 120.2(4) . . ? F2 C17 C16 120.9(4) . . ? C18 C17 C16 118.8(4) . . ? C17 C18 F3 119.1(4) . . ? C17 C18 C19 121.3(4) . . ? F3 C18 C19 119.6(4) . . ? F4 C19 C18 121.2(3) . . ? F4 C19 C20 120.3(4) . . ? C18 C19 C20 118.5(4) . . ? F5 C20 C15 118.9(3) . . ? F5 C20 C19 118.5(4) . . ? C15 C20 C19 122.6(4) . . ? C22 C21 C26 115.4(3) . . ? C22 C21 C9 122.3(3) . . ? C26 C21 C9 122.3(3) . . ? F6 C22 C23 116.6(4) . . ? F6 C22 C21 119.8(3) . . ? C23 C22 C21 123.5(3) . . ? F7 C23 C24 119.9(3) . . ? F7 C23 C22 120.9(3) . . ? C24 C23 C22 119.1(4) . . ? F8 C24 C25 120.5(4) . . ? F8 C24 C23 119.7(4) . . ? C25 C24 C23 119.7(3) . . ? F9 C25 C24 119.1(3) . . ? F9 C25 C26 120.8(4) . . ? C24 C25 C26 120.1(3) . . ? F10 C26 C25 117.6(3) . . ? F10 C26 C21 120.3(3) . . ? C25 C26 C21 122.1(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 0.4(4) . . . . ? C4 N1 C1 C14 -179.4(3) . . . . ? N1 C1 C2 C3 -0.7(4) . . . . ? C14 C1 C2 C3 179.1(4) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C1 N1 C4 C3 0.1(4) . . . . ? C1 N1 C4 C5 -179.9(3) . . . . ? C2 C3 C4 N1 -0.5(4) . . . . ? C2 C3 C4 C5 179.5(4) . . . . ? C8 N2 C5 C4 -176.9(3) . . . . ? C8 N2 C5 C6 0.8(4) . . . . ? N1 C4 C5 N2 6.3(6) . . . . ? C3 C4 C5 N2 -173.7(4) . . . . ? N1 C4 C5 C6 -171.1(3) . . . . ? C3 C4 C5 C6 8.9(6) . . . . ? N2 C5 C6 C7 -1.3(4) . . . . ? C4 C5 C6 C7 176.4(3) . . . . ? C5 C6 C7 C8 1.1(4) . . . . ? C5 N2 C8 C9 -179.2(3) . . . . ? C5 N2 C8 C7 -0.1(4) . . . . ? C6 C7 C8 C9 178.3(4) . . . . ? C6 C7 C8 N2 -0.7(4) . . . . ? N2 C8 C9 C10 3.4(6) . . . . ? C7 C8 C9 C10 -175.5(3) . . . . ? N2 C8 C9 C21 -176.0(3) . . . . ? C7 C8 C9 C21 5.1(6) . . . . ? C13 N3 C10 C11 0.2(4) . . . . ? C13 N3 C10 C9 177.4(3) . . . . ? C8 C9 C10 N3 0.6(6) . . . . ? C21 C9 C10 N3 -180.0(3) . . . . ? C8 C9 C10 C11 177.1(4) . . . . ? C21 C9 C10 C11 -3.5(6) . . . . ? N3 C10 C11 C12 -0.5(4) . . . . ? C9 C10 C11 C12 -177.4(4) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C10 N3 C13 C12 0.2(5) . . . . ? C11 C12 C13 N3 -0.4(5) . . . . ? N1 C1 C14 O1 -0.9(6) . . . . ? C2 C1 C14 O1 179.3(4) . . . . ? N1 C1 C14 C15 180.0(3) . . . . ? C2 C1 C14 C15 0.2(6) . . . . ? O1 C14 C15 C20 -90.6(5) . . . . ? C1 C14 C15 C20 88.5(5) . . . . ? O1 C14 C15 C16 83.8(5) . . . . ? C1 C14 C15 C16 -97.0(4) . . . . ? C20 C15 C16 F1 179.9(3) . . . . ? C14 C15 C16 F1 5.1(5) . . . . ? C20 C15 C16 C17 0.1(6) . . . . ? C14 C15 C16 C17 -174.6(4) . . . . ? F1 C16 C17 F2 1.0(6) . . . . ? C15 C16 C17 F2 -179.3(3) . . . . ? F1 C16 C17 C18 -179.4(3) . . . . ? C15 C16 C17 C18 0.3(6) . . . . ? F2 C17 C18 F3 -0.6(6) . . . . ? C16 C17 C18 F3 179.8(3) . . . . ? F2 C17 C18 C19 179.9(3) . . . . ? C16 C17 C18 C19 0.3(6) . . . . ? C17 C18 C19 F4 179.4(4) . . . . ? F3 C18 C19 F4 -0.1(6) . . . . ? C17 C18 C19 C20 -1.4(6) . . . . ? F3 C18 C19 C20 179.2(3) . . . . ? C16 C15 C20 F5 -178.9(3) . . . . ? C14 C15 C20 F5 -4.2(5) . . . . ? C16 C15 C20 C19 -1.2(6) . . . . ? C14 C15 C20 C19 173.4(4) . . . . ? F4 C19 C20 F5 -1.2(6) . . . . ? C18 C19 C20 F5 179.5(3) . . . . ? F4 C19 C20 C15 -178.9(3) . . . . ? C18 C19 C20 C15 1.9(6) . . . . ? C8 C9 C21 C22 117.0(4) . . . . ? C10 C9 C21 C22 -62.5(5) . . . . ? C8 C9 C21 C26 -61.4(5) . . . . ? C10 C9 C21 C26 119.2(4) . . . . ? C26 C21 C22 F6 177.0(3) . . . . ? C9 C21 C22 F6 -1.5(6) . . . . ? C26 C21 C22 C23 -0.4(6) . . . . ? C9 C21 C22 C23 -178.9(3) . . . . ? F6 C22 C23 F7 1.4(6) . . . . ? C21 C22 C23 F7 178.8(4) . . . . ? F6 C22 C23 C24 -176.1(3) . . . . ? C21 C22 C23 C24 1.3(6) . . . . ? F7 C23 C24 F8 0.9(6) . . . . ? C22 C23 C24 F8 178.4(3) . . . . ? F7 C23 C24 C25 -178.3(4) . . . . ? C22 C23 C24 C25 -0.8(6) . . . . ? F8 C24 C25 F9 -1.1(6) . . . . ? C23 C24 C25 F9 178.1(4) . . . . ? F8 C24 C25 C26 -179.8(3) . . . . ? C23 C24 C25 C26 -0.6(6) . . . . ? F9 C25 C26 F10 2.7(6) . . . . ? C24 C25 C26 F10 -178.6(4) . . . . ? F9 C25 C26 C21 -177.1(3) . . . . ? C24 C25 C26 C21 1.5(6) . . . . ? C22 C21 C26 F10 179.2(3) . . . . ? C9 C21 C26 F10 -2.4(6) . . . . ? C22 C21 C26 C25 -1.0(6) . . . . ? C9 C21 C26 C25 177.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.183 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 959646'