data_201309138 _audit_creation_date 2013-09-12 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H19 N O2' _chemical_formula_sum 'C24 H19 N O2' _chemical_formula_weight 353.40 _chemical_melting_point ? _chemical_oxdiff_formula C24H19NO2 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'triclinic' _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.5219(5) _cell_length_b 9.7304(8) _cell_length_c 11.5747(9) _cell_angle_alpha 105.945(7) _cell_angle_beta 109.988(6) _cell_angle_gamma 99.912(6) _cell_volume 926.09(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3095 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 72.1820 _cell_measurement_theta_min 4.3440 _exptl_absorpt_coefficient_mu 0.637 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour '' _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description '' _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_unetI/netI 0.0254 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6658 _diffrn_reflns_theta_full 67.06 _diffrn_reflns_theta_max 67.06 _diffrn_reflns_theta_min 4.36 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 29.00 55.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -111.00 -21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -57.0000 60.0000 90 #__ type_ start__ end____ width___ exp.time_ 3 omega -52.00 6.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 57.0000 30.0000 58 #__ type_ start__ end____ width___ exp.time_ 4 omega -115.00 -74.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -30.0000 -30.0000 41 #__ type_ start__ end____ width___ exp.time_ 5 omega -63.00 26.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 57.0000 -150.0000 89 #__ type_ start__ end____ width___ exp.time_ 6 omega -97.00 -28.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -61.0000 -90.0000 69 #__ type_ start__ end____ width___ exp.time_ 7 omega -17.00 28.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 30.0000 150.0000 45 #__ type_ start__ end____ width___ exp.time_ 8 omega -104.00 -66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 178.0000 -30.0000 38 #__ type_ start__ end____ width___ exp.time_ 9 omega 32.00 113.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 -125.0000 -90.0000 81 #__ type_ start__ end____ width___ exp.time_ 10 omega 89.00 178.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 45.0000 90.0000 89 #__ type_ start__ end____ width___ exp.time_ 11 omega 58.00 83.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega 47.00 106.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 -60.0000 59 #__ type_ start__ end____ width___ exp.time_ 13 omega 44.00 140.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -77.0000 -30.0000 96 #__ type_ start__ end____ width___ exp.time_ 14 omega 46.00 84.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -30.0000 38 #__ type_ start__ end____ width___ exp.time_ 15 omega 51.00 110.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -61.0000 120.0000 59 #__ type_ start__ end____ width___ exp.time_ 16 omega 149.00 174.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 45.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 17 omega 93.00 119.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 45.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 18 omega 42.00 90.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -90.0000 48 #__ type_ start__ end____ width___ exp.time_ 19 omega 84.00 114.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -131.0000 -154.0000 30 #__ type_ start__ end____ width___ exp.time_ 20 omega 43.00 69.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -131.0000 -154.0000 26 #__ type_ start__ end____ width___ exp.time_ 21 omega 42.00 81.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 -180.0000 39 #__ type_ start__ end____ width___ exp.time_ 22 omega 89.00 115.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 23 omega 148.00 176.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 -120.0000 28 #__ type_ start__ end____ width___ exp.time_ 24 omega 40.00 75.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -150.0000 35 #__ type_ start__ end____ width___ exp.time_ 25 omega 41.00 159.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -15.0000 60.0000 118 #__ type_ start__ end____ width___ exp.time_ 26 omega 50.00 105.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 -150.0000 55 #__ type_ start__ end____ width___ exp.time_ 27 omega -4.00 42.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 120.0000 46 #__ type_ start__ end____ width___ exp.time_ 28 omega -49.00 30.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 37.0000 -30.0000 79 #__ type_ start__ end____ width___ exp.time_ 29 omega -111.00 -21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -57.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 30 omega -113.00 -12.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -77.0000 0.0000 101 #__ type_ start__ end____ width___ exp.time_ 31 omega 35.00 125.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 -150.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0038283000 _diffrn_orient_matrix_UB_12 -0.1090465000 _diffrn_orient_matrix_UB_13 0.0748027000 _diffrn_orient_matrix_UB_21 0.0874200000 _diffrn_orient_matrix_UB_22 0.1327613000 _diffrn_orient_matrix_UB_23 0.1320663000 _diffrn_orient_matrix_UB_31 -0.1574681000 _diffrn_orient_matrix_UB_32 0.0130188000 _diffrn_orient_matrix_UB_33 0.0037798000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2757 _reflns_number_total 3306 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.158 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.028 _refine_ls_extinction_coef 0.0161(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 247 _refine_ls_number_reflns 3306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0385 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.0543P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1066 _refine_ls_wR_factor_ref 0.1142 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23) 2.b Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C24(H24A,H24B,H24C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.30084(12) 0.55690(12) 0.87978(10) 0.0598(3) Uani 1 1 d . . . O2 O -0.09723(11) 0.44362(13) 0.68259(11) 0.0621(3) Uani 1 1 d . . . N1 N 0.40588(12) 0.47078(14) 0.73456(12) 0.0487(3) Uani 1 1 d . . . C1 C 0.2232(2) 0.20373(18) 0.39163(15) 0.0583(4) Uani 1 1 d . . . H1 H 0.1245 0.1467 0.3266 0.070 Uiso 1 1 calc R . . C2 C 0.3529(2) 0.1952(2) 0.36639(19) 0.0746(5) Uani 1 1 d . . . H2 H 0.3418 0.1328 0.2849 0.090 Uiso 1 1 calc R . . C3 C 0.5005(2) 0.2801(2) 0.4627(2) 0.0737(5) Uani 1 1 d . . . H3 H 0.5880 0.2745 0.4451 0.088 Uiso 1 1 calc R . . C4 C 0.51876(19) 0.3716(2) 0.58302(18) 0.0616(4) Uani 1 1 d . . . H4 H 0.6185 0.4277 0.6467 0.074 Uiso 1 1 calc R . . C5 C 0.38794(16) 0.38145(15) 0.61099(14) 0.0463(3) Uani 1 1 d . . . C6 C 0.23706(16) 0.29698(15) 0.51387(13) 0.0439(3) Uani 1 1 d . . . C7 C 0.10333(14) 0.29920(14) 0.54681(12) 0.0404(3) Uani 1 1 d . . . C8 C 0.12826(14) 0.38005(14) 0.67123(13) 0.0415(3) Uani 1 1 d . . . C9 C 0.28239(15) 0.47528(15) 0.77055(13) 0.0449(3) Uani 1 1 d . . . C10 C 0.56141(17) 0.5653(2) 0.83652(17) 0.0707(5) Uani 1 1 d . . . H10A H 0.6206 0.5032 0.8691 0.106 Uiso 1 1 calc R . . H10B H 0.5497 0.6337 0.9077 0.106 Uiso 1 1 calc R . . H10C H 0.6152 0.6204 0.7992 0.106 Uiso 1 1 calc R . . C11 C 0.00047(14) 0.38222(15) 0.72008(13) 0.0449(3) Uani 1 1 d . . . C12 C 0.00261(14) 0.30873(14) 0.81775(13) 0.0442(3) Uani 1 1 d . . . C13 C -0.08975(17) 0.33442(17) 0.88708(15) 0.0545(4) Uani 1 1 d . . . H13 H -0.1569 0.3919 0.8681 0.065 Uiso 1 1 calc R . . C14 C -0.0829(2) 0.27545(18) 0.98383(16) 0.0645(4) Uani 1 1 d . . . H14 H -0.1442 0.2940 1.0306 0.077 Uiso 1 1 calc R . . C15 C 0.0153(2) 0.18905(19) 1.01067(16) 0.0660(5) Uani 1 1 d . . . H15 H 0.0217 0.1508 1.0770 0.079 Uiso 1 1 calc R . . C16 C 0.1045(2) 0.15859(18) 0.93975(16) 0.0618(4) Uani 1 1 d . . . H16 H 0.1681 0.0976 0.9567 0.074 Uiso 1 1 calc R . . C17 C 0.09909(16) 0.21842(16) 0.84425(14) 0.0509(3) Uani 1 1 d . . . H17 H 0.1599 0.1986 0.7972 0.061 Uiso 1 1 calc R . . C18 C -0.05699(14) 0.20658(14) 0.44674(13) 0.0424(3) Uani 1 1 d . . . C19 C -0.12416(17) 0.23325(17) 0.33111(14) 0.0524(3) Uani 1 1 d . . . H19 H -0.0701 0.3116 0.3168 0.063 Uiso 1 1 calc R . . C20 C -0.27080(18) 0.14413(18) 0.23714(14) 0.0583(4) Uani 1 1 d . . . H20 H -0.3143 0.1640 0.1606 0.070 Uiso 1 1 calc R . . C21 C -0.35434(17) 0.02580(17) 0.25447(14) 0.0547(4) Uani 1 1 d . . . C22 C -0.28890(17) 0.00251(15) 0.37151(15) 0.0523(3) Uani 1 1 d . . . H22 H -0.3444 -0.0742 0.3866 0.063 Uiso 1 1 calc R . . C23 C -0.14236(15) 0.09126(15) 0.46657(13) 0.0464(3) Uani 1 1 d . . . H23 H -0.1007 0.0735 0.5444 0.056 Uiso 1 1 calc R . . C24 C -0.5119(2) -0.0759(2) 0.14991(18) 0.0831(6) Uani 1 1 d . . . H24A H -0.5651 -0.0203 0.1021 0.125 Uiso 1 1 calc R . . H24B H -0.5732 -0.1149 0.1909 0.125 Uiso 1 1 calc R . . H24C H -0.4976 -0.1571 0.0902 0.125 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 O1 0.0470(6) 0.0647(6) 0.0481(6) 0.0020(5) 0.0168(4) 0.0054(5) O2 0.0455(6) 0.0775(7) 0.0751(7) 0.0351(6) 0.0278(5) 0.0275(5) N1 0.0328(5) 0.0538(6) 0.0526(7) 0.0159(5) 0.0149(5) 0.0065(5) C1 0.0643(9) 0.0644(9) 0.0517(8) 0.0201(7) 0.0291(7) 0.0222(7) C2 0.0885(13) 0.0866(12) 0.0697(11) 0.0259(10) 0.0522(10) 0.0385(10) C3 0.0684(11) 0.0921(13) 0.0896(13) 0.0386(11) 0.0547(10) 0.0379(10) C4 0.0469(8) 0.0729(10) 0.0775(11) 0.0318(8) 0.0340(8) 0.0220(7) C5 0.0423(7) 0.0498(7) 0.0563(8) 0.0256(6) 0.0249(6) 0.0163(6) C6 0.0460(7) 0.0460(7) 0.0477(7) 0.0221(6) 0.0232(6) 0.0159(6) C7 0.0394(6) 0.0412(6) 0.0429(7) 0.0194(5) 0.0160(5) 0.0118(5) C8 0.0351(6) 0.0446(7) 0.0437(7) 0.0160(5) 0.0156(5) 0.0101(5) C9 0.0386(7) 0.0461(7) 0.0459(7) 0.0135(6) 0.0160(5) 0.0102(5) C10 0.0368(7) 0.0861(12) 0.0661(10) 0.0121(9) 0.0144(7) 0.0023(8) C11 0.0332(6) 0.0471(7) 0.0455(7) 0.0088(6) 0.0139(5) 0.0081(5) C12 0.0359(6) 0.0439(7) 0.0426(7) 0.0061(5) 0.0159(5) 0.0035(5) C13 0.0465(7) 0.0537(8) 0.0596(9) 0.0110(7) 0.0282(7) 0.0083(6) C14 0.0661(10) 0.0625(9) 0.0599(9) 0.0097(7) 0.0385(8) 0.0010(8) C15 0.0754(11) 0.0612(9) 0.0523(9) 0.0185(7) 0.0273(8) -0.0010(8) C16 0.0618(9) 0.0573(9) 0.0625(9) 0.0245(7) 0.0216(8) 0.0120(7) C17 0.0462(7) 0.0535(8) 0.0506(8) 0.0147(6) 0.0219(6) 0.0114(6) C18 0.0396(6) 0.0426(7) 0.0410(7) 0.0128(5) 0.0142(5) 0.0110(5) C19 0.0524(8) 0.0543(8) 0.0476(7) 0.0222(6) 0.0161(6) 0.0120(6) C20 0.0570(8) 0.0685(9) 0.0400(7) 0.0185(7) 0.0103(6) 0.0178(7) C21 0.0456(7) 0.0538(8) 0.0466(8) 0.0037(6) 0.0109(6) 0.0115(6) C22 0.0464(7) 0.0414(7) 0.0599(9) 0.0136(6) 0.0182(6) 0.0057(6) C23 0.0449(7) 0.0466(7) 0.0448(7) 0.0183(6) 0.0141(6) 0.0124(6) C24 0.0598(10) 0.0842(13) 0.0602(11) -0.0009(9) 0.0035(8) 0.0013(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.2283(16) . ? O2 C11 1.2118(17) . ? N1 C5 1.3890(19) . ? N1 C9 1.3786(17) . ? N1 C10 1.4735(18) . ? C1 H1 0.9300 . ? C1 C2 1.373(2) . ? C1 C6 1.403(2) . ? C2 H2 0.9300 . ? C2 C3 1.387(3) . ? C3 H3 0.9300 . ? C3 C4 1.365(3) . ? C4 H4 0.9300 . ? C4 C5 1.402(2) . ? C5 C6 1.409(2) . ? C6 C7 1.4505(17) . ? C7 C8 1.3523(18) . ? C7 C18 1.4927(17) . ? C8 C9 1.4585(17) . ? C8 C11 1.5078(17) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.491(2) . ? C12 C13 1.3884(19) . ? C12 C17 1.394(2) . ? C13 H13 0.9300 . ? C13 C14 1.380(2) . ? C14 H14 0.9300 . ? C14 C15 1.375(3) . ? C15 H15 0.9300 . ? C15 C16 1.383(2) . ? C16 H16 0.9300 . ? C16 C17 1.374(2) . ? C17 H17 0.9300 . ? C18 C19 1.3894(19) . ? C18 C23 1.3884(18) . ? C19 H19 0.9300 . ? C19 C20 1.383(2) . ? C20 H20 0.9300 . ? C20 C21 1.385(2) . ? C21 C22 1.384(2) . ? C21 C24 1.511(2) . ? C22 H22 0.9300 . ? C22 C23 1.3845(19) . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 N1 C10 121.04(12) . . ? C9 N1 C5 122.95(11) . . ? C9 N1 C10 116.00(12) . . ? C2 C1 H1 119.4 . . ? C2 C1 C6 121.12(16) . . ? C6 C1 H1 119.4 . . ? C1 C2 H2 120.1 . . ? C1 C2 C3 119.83(16) . . ? C3 C2 H2 120.1 . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.78(15) . . ? C4 C3 H3 119.6 . . ? C3 C4 H4 119.8 . . ? C3 C4 C5 120.30(16) . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 120.64(14) . . ? N1 C5 C6 119.69(12) . . ? C4 C5 C6 119.66(14) . . ? C1 C6 C5 118.31(13) . . ? C1 C6 C7 122.21(13) . . ? C5 C6 C7 119.26(12) . . ? C6 C7 C18 120.13(12) . . ? C8 C7 C6 118.65(12) . . ? C8 C7 C18 121.13(11) . . ? C7 C8 C9 122.70(12) . . ? C7 C8 C11 123.61(11) . . ? C9 C8 C11 113.69(11) . . ? O1 C9 N1 121.76(12) . . ? O1 C9 C8 121.75(12) . . ? N1 C9 C8 116.48(12) . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C8 120.84(13) . . ? O2 C11 C12 122.16(12) . . ? C12 C11 C8 116.99(11) . . ? C13 C12 C11 119.38(13) . . ? C13 C12 C17 119.09(14) . . ? C17 C12 C11 121.50(12) . . ? C12 C13 H13 119.7 . . ? C14 C13 C12 120.64(15) . . ? C14 C13 H13 119.7 . . ? C13 C14 H14 120.2 . . ? C15 C14 C13 119.56(15) . . ? C15 C14 H14 120.2 . . ? C14 C15 H15 119.7 . . ? C14 C15 C16 120.52(16) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.04(16) . . ? C17 C16 H16 120.0 . . ? C12 C17 H17 120.0 . . ? C16 C17 C12 120.10(14) . . ? C16 C17 H17 120.0 . . ? C19 C18 C7 120.78(12) . . ? C23 C18 C7 120.86(12) . . ? C23 C18 C19 118.36(12) . . ? C18 C19 H19 119.8 . . ? C20 C19 C18 120.43(14) . . ? C20 C19 H19 119.8 . . ? C19 C20 H20 119.3 . . ? C19 C20 C21 121.44(14) . . ? C21 C20 H20 119.3 . . ? C20 C21 C24 121.77(16) . . ? C22 C21 C20 117.87(13) . . ? C22 C21 C24 120.36(16) . . ? C21 C22 H22 119.4 . . ? C21 C22 C23 121.21(14) . . ? C23 C22 H22 119.4 . . ? C18 C23 H23 119.7 . . ? C22 C23 C18 120.63(13) . . ? C22 C23 H23 119.7 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 O2 C11 C12 C13 -12.5(2) . . . . ? O2 C11 C12 C17 169.58(13) . . . . ? N1 C5 C6 C1 -177.74(13) . . . . ? N1 C5 C6 C7 -2.99(19) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C1 C6 C7 C8 173.06(13) . . . . ? C1 C6 C7 C18 -3.44(19) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? C2 C1 C6 C7 -175.00(15) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 N1 177.97(15) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C4 C5 C6 C1 0.7(2) . . . . ? C4 C5 C6 C7 175.42(13) . . . . ? C5 N1 C9 O1 -178.88(13) . . . . ? C5 N1 C9 C8 0.03(19) . . . . ? C5 C6 C7 C8 -1.47(18) . . . . ? C5 C6 C7 C18 -177.97(11) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C6 C7 C8 C9 5.41(19) . . . . ? C6 C7 C8 C11 -175.38(11) . . . . ? C6 C7 C18 C19 -63.54(17) . . . . ? C6 C7 C18 C23 116.15(14) . . . . ? C7 C8 C9 O1 174.15(13) . . . . ? C7 C8 C9 N1 -4.76(19) . . . . ? C7 C8 C11 O2 -70.64(18) . . . . ? C7 C8 C11 C12 110.62(14) . . . . ? C7 C18 C19 C20 178.06(13) . . . . ? C7 C18 C23 C22 -177.85(12) . . . . ? C8 C7 C18 C19 120.05(15) . . . . ? C8 C7 C18 C23 -60.26(18) . . . . ? C8 C11 C12 C13 166.23(12) . . . . ? C8 C11 C12 C17 -11.69(18) . . . . ? C9 N1 C5 C4 -174.70(13) . . . . ? C9 N1 C5 C6 3.7(2) . . . . ? C9 C8 C11 O2 108.64(15) . . . . ? C9 C8 C11 C12 -70.11(15) . . . . ? C10 N1 C5 C4 4.2(2) . . . . ? C10 N1 C5 C6 -177.45(13) . . . . ? C10 N1 C9 O1 2.2(2) . . . . ? C10 N1 C9 C8 -178.88(13) . . . . ? C11 C8 C9 O1 -5.13(19) . . . . ? C11 C8 C9 N1 175.96(12) . . . . ? C11 C12 C13 C14 -175.96(13) . . . . ? C11 C12 C17 C16 176.60(13) . . . . ? C12 C13 C14 C15 -0.7(2) . . . . ? C13 C12 C17 C16 -1.3(2) . . . . ? C13 C14 C15 C16 -1.3(2) . . . . ? C14 C15 C16 C17 2.0(2) . . . . ? C15 C16 C17 C12 -0.6(2) . . . . ? C17 C12 C13 C14 2.0(2) . . . . ? C18 C7 C8 C9 -178.13(11) . . . . ? C18 C7 C8 C11 1.1(2) . . . . ? C18 C19 C20 C21 -0.5(2) . . . . ? C19 C18 C23 C22 1.8(2) . . . . ? C19 C20 C21 C22 2.4(2) . . . . ? C19 C20 C21 C24 -177.55(16) . . . . ? C20 C21 C22 C23 -2.1(2) . . . . ? C21 C22 C23 C18 0.1(2) . . . . ? C23 C18 C19 C20 -1.6(2) . . . . ? C24 C21 C22 C23 177.77(15) . . . . ?