data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jay Siegel' 'Kim K Baldridge' 'Derik K. Frantz' 'Anthony Linden' 'Ashley A. Sullivan' 'Yoshizumi Yasui' _publ_contact_author_name 'Jay Siegel' _publ_contact_author_email JSS@OCI.UZH.CH _publ_section_title ; Synthesis, X-ray crystal structures, and computational studies of 1,1'-bridged 4,4'-diaryl-2,2'-bibenzimidazoles: novel building blocks for supramolecular structure." ; # Attachment '3a.cif' data_SG0611 _database_code_depnum_ccdc_archive 'CCDC 710114' _audit_creation_method SHELXL-97 _audit_creation_date 06-02-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C38 H32 N4 O2' _chemical_formula_sum 'C38 H32 N4 O2' _chemical_formula_weight 576.70 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 76 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 64 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 4 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2157(3) _cell_length_b 11.9363(5) _cell_length_c 12.9452(5) _cell_angle_alpha 66.5184(17) _cell_angle_beta 89.148(2) _cell_angle_gamma 86.525(2) _cell_volume 1445.05(9) _cell_formula_units_Z 2 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 8250 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.0830 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: dichloromethane / hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.700(2) Frames collected: 383 Seconds exposure per frame: 100 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 33.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 36774 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 30.00 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 8409 _reflns_number_gt 5233 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.0822P] 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 0.105(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8408 _refine_ls_number_parameters 402 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1318 _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 _refine_diff_density_max 0.327 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.082 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 O14 O -0.24263(10) 0.38365(11) 0.45398(10) 0.0407(3) Uani 1 1 d . . . O34 O -0.17865(10) -0.40173(11) 1.06097(10) 0.0386(3) Uani 1 1 d . . . N1 N 0.33575(11) 0.12422(11) 0.63282(11) 0.0282(3) Uani 1 1 d . . . N8 N 0.54812(11) 0.07200(12) 0.61246(11) 0.0275(3) Uani 1 1 d . . . N21 N 0.35228(11) -0.10586(11) 0.84937(11) 0.0283(3) Uani 1 1 d . . . N28 N 0.55704(11) -0.05096(12) 0.86272(11) 0.0277(3) Uani 1 1 d . . . C2 C 0.37580(14) 0.19354(14) 0.52429(13) 0.0265(3) Uani 1 1 d . . . C3 C 0.30165(14) 0.28031(14) 0.43383(13) 0.0273(4) Uani 1 1 d . . . C4 C 0.36868(15) 0.33357(14) 0.33296(14) 0.0305(4) Uani 1 1 d . . . H4 H 0.3224 0.3938 0.2704 0.037 Uiso 1 1 calc R . . C5 C 0.50108(15) 0.30311(14) 0.31856(14) 0.0302(4) Uani 1 1 d . . . C6 C 0.57162(15) 0.21474(14) 0.40733(14) 0.0298(4) Uani 1 1 d . . . H6 H 0.6603 0.1911 0.3988 0.036 Uiso 1 1 calc R . . C7 C 0.50740(14) 0.16188(14) 0.50958(13) 0.0269(4) Uani 1 1 d . . . C9 C 0.43985(14) 0.05391(14) 0.68125(13) 0.0277(4) Uani 1 1 d . . . C10 C 0.56546(16) 0.36727(16) 0.20627(14) 0.0365(4) Uani 1 1 d . . . H101 H 0.6549 0.3853 0.2184 0.055 Uiso 1 1 calc R . . H102 H 0.5148 0.4438 0.1629 0.055 Uiso 1 1 calc R . . H103 H 0.5685 0.3143 0.1646 0.055 Uiso 1 1 calc R . . C11 C 0.15965(14) 0.30791(14) 0.44290(13) 0.0279(4) Uani 1 1 d . . . C12 C 0.10515(16) 0.31561(16) 0.53836(15) 0.0372(4) Uani 1 1 d . . . H12 H 0.1606 0.3033 0.6007 0.045 Uiso 1 1 calc R . . C13 C -0.02829(15) 0.34085(16) 0.54570(15) 0.0373(4) Uani 1 1 d . . . H13 H -0.0630 0.3467 0.6120 0.045 Uiso 1 1 calc R . . C14 C -0.11028(14) 0.35746(14) 0.45646(14) 0.0309(4) Uani 1 1 d . . . C15 C -0.05817(16) 0.34752(18) 0.36120(15) 0.0430(5) Uani 1 1 d . . . H15 H -0.1142 0.3572 0.2999 0.052 Uiso 1 1 calc R . . C16 C 0.07449(16) 0.32367(17) 0.35458(14) 0.0394(4) Uani 1 1 d . . . H16 H 0.1087 0.3178 0.2882 0.047 Uiso 1 1 calc R . . C17 C -0.30254(16) 0.38472(17) 0.55321(16) 0.0408(4) Uani 1 1 d . . . H171 H -0.2838 0.3054 0.6158 0.061 Uiso 1 1 calc R . . H172 H -0.3976 0.3998 0.5412 0.061 Uiso 1 1 calc R . . H173 H -0.2676 0.4496 0.5711 0.061 Uiso 1 1 calc R . . C18 C 0.66126(14) -0.01621(14) 0.62996(14) 0.0305(4) Uani 1 1 d . . . H181 H 0.6865 -0.0159 0.5557 0.037 Uiso 1 1 calc R . . H182 H 0.6322 -0.0988 0.6765 0.037 Uiso 1 1 calc R . . C22 C 0.40265(14) -0.17503(14) 0.95693(13) 0.0265(3) Uani 1 1 d . . . C23 C 0.34384(14) -0.26519(14) 1.04948(13) 0.0273(3) Uani 1 1 d . . . C24 C 0.42239(15) -0.31941(15) 1.14587(14) 0.0307(4) Uani 1 1 d . . . H24 H 0.3874 -0.3828 1.2092 0.037 Uiso 1 1 calc R . . C25 C 0.54973(15) -0.28656(15) 1.15547(14) 0.0323(4) Uani 1 1 d . . . C26 C 0.60445(15) -0.19420(15) 1.06515(14) 0.0314(4) Uani 1 1 d . . . H26 H 0.6892 -0.1681 1.0703 0.038 Uiso 1 1 calc R . . C27 C 0.52989(14) -0.14154(14) 0.96671(13) 0.0272(4) Uani 1 1 d . . . C29 C 0.44596(14) -0.03468(14) 0.79741(13) 0.0277(4) Uani 1 1 d . . . C30 C 0.62606(17) -0.35207(17) 1.26336(15) 0.0406(4) Uani 1 1 d . . . H301 H 0.7194 -0.3583 1.2464 0.061 Uiso 1 1 calc R . . H302 H 0.5947 -0.4343 1.3026 0.061 Uiso 1 1 calc R . . H303 H 0.6139 -0.3063 1.3114 0.061 Uiso 1 1 calc R . . C31 C 0.20613(15) -0.29787(14) 1.04781(13) 0.0280(4) Uani 1 1 d . . . C32 C 0.14310(15) -0.28820(15) 0.94985(14) 0.0329(4) Uani 1 1 d . . . H32 H 0.1887 -0.2578 0.8806 0.039 Uiso 1 1 calc R . . C33 C 0.01565(15) -0.32174(15) 0.95066(14) 0.0344(4) Uani 1 1 d . . . H33 H -0.0245 -0.3153 0.8826 0.041 Uiso 1 1 calc R . . C34 C -0.05340(15) -0.36461(14) 1.05007(14) 0.0313(4) Uani 1 1 d . . . C35 C 0.00614(16) -0.37193(17) 1.14851(15) 0.0390(4) Uani 1 1 d . . . H35 H -0.0409 -0.3995 1.2172 0.047 Uiso 1 1 calc R . . C36 C 0.13339(16) -0.33921(16) 1.14663(14) 0.0374(4) Uani 1 1 d . . . H36 H 0.1728 -0.3450 1.2147 0.045 Uiso 1 1 calc R . . C37 C -0.24439(16) -0.39146(17) 0.96124(15) 0.0403(4) Uani 1 1 d . . . H371 H -0.2480 -0.3060 0.9069 0.060 Uiso 1 1 calc R . . H372 H -0.3337 -0.4183 0.9796 0.060 Uiso 1 1 calc R . . H373 H -0.1968 -0.4430 0.9285 0.060 Uiso 1 1 calc R . . C38 C 0.65668(14) 0.03896(15) 0.84177(15) 0.0307(4) Uani 1 1 d . . . H381 H 0.6803 0.0410 0.9149 0.037 Uiso 1 1 calc R . . H382 H 0.6161 0.1206 0.7943 0.037 Uiso 1 1 calc R . . C41 C 0.78283(14) 0.00309(14) 0.68498(14) 0.0292(4) Uani 1 1 d . . . C42 C 0.90307(15) -0.00609(16) 0.63546(15) 0.0377(4) Uani 1 1 d . . . H42 H 0.9048 -0.0180 0.5671 0.045 Uiso 1 1 calc R . . C43 C 1.02040(16) 0.00198(18) 0.68464(17) 0.0452(5) Uani 1 1 d . . . H43 H 1.1015 -0.0047 0.6501 0.054 Uiso 1 1 calc R . . C44 C 1.01879(16) 0.01963(17) 0.78308(17) 0.0438(5) Uani 1 1 d . . . H44 H 1.0985 0.0260 0.8166 0.053 Uiso 1 1 calc R . . C45 C 0.89990(15) 0.02803(15) 0.83324(16) 0.0360(4) Uani 1 1 d . . . H45 H 0.8992 0.0399 0.9016 0.043 Uiso 1 1 calc R . . C46 C 0.78186(14) 0.01952(14) 0.78591(14) 0.0292(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 O14 0.0235(6) 0.0572(8) 0.0395(7) -0.0181(6) -0.0023(5) 0.0029(5) O34 0.0273(6) 0.0534(8) 0.0370(7) -0.0192(6) 0.0048(5) -0.0095(5) N1 0.0232(7) 0.0304(7) 0.0302(8) -0.0113(6) 0.0004(5) -0.0021(5) N8 0.0196(6) 0.0307(7) 0.0317(8) -0.0119(6) 0.0011(5) -0.0009(5) N21 0.0233(7) 0.0311(7) 0.0293(8) -0.0109(6) 0.0001(5) 0.0000(5) N28 0.0205(7) 0.0321(7) 0.0307(8) -0.0129(6) 0.0001(5) -0.0009(5) C2 0.0249(8) 0.0278(8) 0.0290(9) -0.0132(7) 0.0005(6) -0.0037(6) C3 0.0263(8) 0.0263(8) 0.0319(9) -0.0141(7) 0.0003(6) -0.0026(6) C4 0.0315(9) 0.0284(9) 0.0314(9) -0.0116(7) -0.0010(7) -0.0022(6) C5 0.0312(9) 0.0305(9) 0.0328(9) -0.0162(7) 0.0036(7) -0.0057(6) C6 0.0241(8) 0.0338(9) 0.0363(10) -0.0185(8) 0.0047(7) -0.0047(6) C7 0.0239(8) 0.0285(8) 0.0310(9) -0.0144(7) 0.0003(6) -0.0033(6) C9 0.0212(8) 0.0301(8) 0.0327(9) -0.0133(7) 0.0016(6) -0.0036(6) C10 0.0370(10) 0.0372(10) 0.0352(10) -0.0144(8) 0.0085(7) -0.0047(7) C11 0.0260(8) 0.0268(8) 0.0293(9) -0.0096(7) -0.0007(6) -0.0011(6) C12 0.0303(9) 0.0522(11) 0.0345(10) -0.0236(9) -0.0062(7) 0.0049(7) C13 0.0293(9) 0.0521(11) 0.0355(10) -0.0235(9) -0.0008(7) 0.0042(7) C14 0.0237(8) 0.0314(9) 0.0340(10) -0.0094(7) -0.0015(6) -0.0008(6) C15 0.0311(10) 0.0664(13) 0.0305(10) -0.0189(9) -0.0066(7) 0.0023(8) C16 0.0314(9) 0.0604(12) 0.0267(9) -0.0182(9) -0.0007(7) 0.0006(8) C17 0.0292(9) 0.0506(11) 0.0455(11) -0.0227(9) 0.0044(8) 0.0006(7) C18 0.0233(8) 0.0333(9) 0.0378(10) -0.0177(8) 0.0005(6) 0.0012(6) C22 0.0239(8) 0.0288(8) 0.0287(9) -0.0140(7) -0.0007(6) 0.0019(6) C23 0.0274(8) 0.0273(8) 0.0301(9) -0.0147(7) -0.0005(6) 0.0007(6) C24 0.0330(9) 0.0304(9) 0.0295(9) -0.0131(7) 0.0005(7) 0.0001(6) C25 0.0326(9) 0.0349(9) 0.0328(9) -0.0182(8) -0.0054(7) 0.0075(7) C26 0.0238(8) 0.0377(9) 0.0363(10) -0.0191(8) -0.0036(7) 0.0027(6) C27 0.0233(8) 0.0309(8) 0.0307(9) -0.0162(7) 0.0004(6) 0.0017(6) C29 0.0205(8) 0.0303(8) 0.0319(9) -0.0124(7) 0.0011(6) 0.0009(6) C30 0.0389(10) 0.0488(11) 0.0347(10) -0.0179(9) -0.0087(8) 0.0051(8) C31 0.0297(8) 0.0271(8) 0.0282(9) -0.0120(7) 0.0011(6) -0.0019(6) C32 0.0308(9) 0.0400(10) 0.0275(9) -0.0127(8) 0.0039(7) -0.0054(7) C33 0.0322(9) 0.0446(10) 0.0283(9) -0.0159(8) 0.0004(7) -0.0058(7) C34 0.0263(8) 0.0333(9) 0.0346(10) -0.0137(8) 0.0039(7) -0.0032(6) C35 0.0354(10) 0.0538(11) 0.0275(9) -0.0151(8) 0.0074(7) -0.0106(8) C36 0.0367(10) 0.0498(11) 0.0269(9) -0.0157(8) 0.0005(7) -0.0068(8) C37 0.0309(9) 0.0496(11) 0.0428(11) -0.0206(9) -0.0010(7) -0.0054(7) C38 0.0237(8) 0.0323(9) 0.0403(10) -0.0188(8) 0.0026(7) -0.0032(6) C41 0.0221(8) 0.0278(8) 0.0370(10) -0.0122(7) 0.0015(6) -0.0006(6) C42 0.0273(9) 0.0450(10) 0.0426(11) -0.0195(9) 0.0051(7) -0.0008(7) C43 0.0223(9) 0.0591(12) 0.0545(13) -0.0234(10) 0.0039(8) -0.0001(8) C44 0.0234(9) 0.0540(12) 0.0534(12) -0.0204(10) -0.0037(8) -0.0045(7) C45 0.0255(9) 0.0418(10) 0.0432(10) -0.0192(8) -0.0015(7) -0.0041(7) C46 0.0225(8) 0.0276(8) 0.0373(10) -0.0128(7) 0.0013(6) -0.0021(6) _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 O14 C14 1.3671(18) . ? O14 C17 1.419(2) . ? O34 C34 1.3664(18) . ? O34 C37 1.422(2) . ? N1 C9 1.3118(19) . ? N1 C2 1.3869(19) . ? N8 C9 1.3818(19) . ? N8 C7 1.386(2) . ? N8 C18 1.4717(19) . ? N21 C29 1.3093(19) . ? N21 C22 1.3924(19) . ? N28 C29 1.3825(19) . ? N28 C27 1.387(2) . ? N28 C38 1.4676(19) . ? C2 C7 1.405(2) . ? C2 C3 1.408(2) . ? C3 C4 1.394(2) . ? C3 C11 1.481(2) . ? C4 C5 1.408(2) . ? C4 H4 0.9500 . ? C5 C6 1.385(2) . ? C5 C10 1.509(2) . ? C6 C7 1.393(2) . ? C6 H6 0.9500 . ? C9 C29 1.453(2) . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 C12 1.382(2) . ? C11 C16 1.392(2) . ? C12 C13 1.388(2) . ? C12 H12 0.9500 . ? C13 C14 1.379(2) . ? C13 H13 0.9500 . ? C14 C15 1.381(2) . ? C15 C16 1.376(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 C41 1.515(2) . ? C18 H181 0.9900 . ? C18 H182 0.9900 . ? C22 C27 1.405(2) . ? C22 C23 1.408(2) . ? C23 C24 1.394(2) . ? C23 C31 1.485(2) . ? C24 C25 1.402(2) . ? C24 H24 0.9500 . ? C25 C26 1.387(2) . ? C25 C30 1.503(2) . ? C26 C27 1.390(2) . ? C26 H26 0.9500 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 C32 1.391(2) . ? C31 C36 1.395(2) . ? C32 C33 1.384(2) . ? C32 H32 0.9500 . ? C33 C34 1.381(2) . ? C33 H33 0.9500 . ? C34 C35 1.389(2) . ? C35 C36 1.377(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H371 0.9800 . ? C37 H372 0.9800 . ? C37 H373 0.9800 . ? C38 C46 1.511(2) . ? C38 H381 0.9900 . ? C38 H382 0.9900 . ? C41 C42 1.396(2) . ? C41 C46 1.396(2) . ? C42 C43 1.392(2) . ? C42 H42 0.9500 . ? C43 C44 1.372(3) . ? C43 H43 0.9500 . ? C44 C45 1.386(2) . ? C44 H44 0.9500 . ? C45 C46 1.388(2) . ? C45 H45 0.9500 . ? 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 C14 O14 C17 118.04(13) . . ? C34 O34 C37 117.24(13) . . ? C9 N1 C2 104.30(12) . . ? C9 N8 C7 105.52(12) . . ? C9 N8 C18 125.30(13) . . ? C7 N8 C18 125.31(13) . . ? C29 N21 C22 104.60(12) . . ? C29 N28 C27 105.53(12) . . ? C29 N28 C38 125.21(13) . . ? C27 N28 C38 125.38(13) . . ? N1 C2 C7 110.50(13) . . ? N1 C2 C3 128.77(13) . . ? C7 C2 C3 120.64(14) . . ? C4 C3 C2 115.66(14) . . ? C4 C3 C11 121.92(14) . . ? C2 C3 C11 122.31(14) . . ? C3 C4 C5 123.70(15) . . ? C3 C4 H4 118.1 . . ? C5 C4 H4 118.1 . . ? C6 C5 C4 119.98(15) . . ? C6 C5 C10 120.33(14) . . ? C4 C5 C10 119.70(15) . . ? C5 C6 C7 117.34(14) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? N8 C7 C6 131.86(14) . . ? N8 C7 C2 105.50(13) . . ? C6 C7 C2 122.63(14) . . ? N1 C9 N8 114.18(14) . . ? N1 C9 C29 124.61(14) . . ? N8 C9 C29 121.20(13) . . ? C5 C10 H101 109.5 . . ? C5 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C5 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C12 C11 C16 117.16(14) . . ? C12 C11 C3 122.60(14) . . ? C16 C11 C3 120.21(15) . . ? C11 C12 C13 121.85(15) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 119.79(16) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? O14 C14 C13 124.83(15) . . ? O14 C14 C15 115.91(14) . . ? C13 C14 C15 119.26(15) . . ? C16 C15 C14 120.34(15) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 121.56(16) . . ? C15 C16 H16 119.2 . . ? C11 C16 H16 119.2 . . ? O14 C17 H171 109.5 . . ? O14 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? O14 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? N8 C18 C41 117.51(13) . . ? N8 C18 H181 107.9 . . ? C41 C18 H181 107.9 . . ? N8 C18 H182 107.9 . . ? C41 C18 H182 107.9 . . ? H181 C18 H182 107.2 . . ? N21 C22 C27 110.05(13) . . ? N21 C22 C23 129.58(14) . . ? C27 C22 C23 120.36(14) . . ? C24 C23 C22 115.32(14) . . ? C24 C23 C31 121.50(14) . . ? C22 C23 C31 123.13(14) . . ? C23 C24 C25 124.30(15) . . ? C23 C24 H24 117.8 . . ? C25 C24 H24 117.8 . . ? C26 C25 C24 119.74(14) . . ? C26 C25 C30 120.50(15) . . ? C24 C25 C30 119.76(15) . . ? C25 C26 C27 117.09(14) . . ? C25 C26 H26 121.5 . . ? C27 C26 H26 121.5 . . ? N28 C27 C26 131.15(14) . . ? N28 C27 C22 105.75(13) . . ? C26 C27 C22 123.10(15) . . ? N21 C29 N28 114.07(14) . . ? N21 C29 C9 125.15(13) . . ? N28 C29 C9 120.77(13) . . ? C25 C30 H301 109.5 . . ? C25 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C25 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C32 C31 C36 116.87(14) . . ? C32 C31 C23 122.71(14) . . ? C36 C31 C23 120.41(14) . . ? C33 C32 C31 121.74(15) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.1 . . ? C34 C33 C32 120.21(15) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? O34 C34 C33 125.19(15) . . ? O34 C34 C35 115.67(14) . . ? C33 C34 C35 119.14(15) . . ? C36 C35 C34 120.01(16) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C35 C36 C31 121.99(16) . . ? C35 C36 H36 119.0 . . ? C31 C36 H36 119.0 . . ? O34 C37 H371 109.5 . . ? O34 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? O34 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? N28 C38 C46 117.31(13) . . ? N28 C38 H381 108.0 . . ? C46 C38 H381 108.0 . . ? N28 C38 H382 108.0 . . ? C46 C38 H382 108.0 . . ? H381 C38 H382 107.2 . . ? C42 C41 C46 118.83(14) . . ? C42 C41 C18 117.12(15) . . ? C46 C41 C18 123.84(13) . . ? C43 C42 C41 121.01(17) . . ? C43 C42 H42 119.5 . . ? C41 C42 H42 119.5 . . ? C44 C43 C42 119.91(16) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C45 119.47(16) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C44 C45 C46 121.52(17) . . ? C44 C45 H45 119.2 . . ? C46 C45 H45 119.2 . . ? C45 C46 C41 119.26(14) . . ? C45 C46 C38 117.84(15) . . ? C41 C46 C38 122.71(13) . . ? 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 C9 N1 C2 C7 0.14(17) . . . . ? C9 N1 C2 C3 176.75(16) . . . . ? N1 C2 C3 C4 -178.42(14) . . . . ? C7 C2 C3 C4 -2.1(2) . . . . ? N1 C2 C3 C11 -2.0(3) . . . . ? C7 C2 C3 C11 174.29(14) . . . . ? C2 C3 C4 C5 1.3(2) . . . . ? C11 C3 C4 C5 -175.13(15) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C3 C4 C5 C10 -179.19(15) . . . . ? C4 C5 C6 C7 -1.8(2) . . . . ? C10 C5 C6 C7 178.06(14) . . . . ? C9 N8 C7 C6 -177.57(16) . . . . ? C18 N8 C7 C6 -18.9(3) . . . . ? C9 N8 C7 C2 0.88(16) . . . . ? C18 N8 C7 C2 159.57(14) . . . . ? C5 C6 C7 N8 179.23(15) . . . . ? C5 C6 C7 C2 1.0(2) . . . . ? N1 C2 C7 N8 -0.66(17) . . . . ? C3 C2 C7 N8 -177.59(13) . . . . ? N1 C2 C7 C6 177.97(14) . . . . ? C3 C2 C7 C6 1.0(2) . . . . ? C2 N1 C9 N8 0.46(18) . . . . ? C2 N1 C9 C29 179.26(14) . . . . ? C7 N8 C9 N1 -0.88(18) . . . . ? C18 N8 C9 N1 -159.57(14) . . . . ? C7 N8 C9 C29 -179.73(14) . . . . ? C18 N8 C9 C29 21.6(2) . . . . ? C4 C3 C11 C12 -144.18(16) . . . . ? C2 C3 C11 C12 39.6(2) . . . . ? C4 C3 C11 C16 37.8(2) . . . . ? C2 C3 C11 C16 -138.41(17) . . . . ? C16 C11 C12 C13 -1.5(3) . . . . ? C3 C11 C12 C13 -179.61(16) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C17 O14 C14 C13 -5.1(2) . . . . ? C17 O14 C14 C15 174.84(16) . . . . ? C12 C13 C14 O14 -179.42(16) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? O14 C14 C15 C16 178.76(16) . . . . ? C13 C14 C15 C16 -1.3(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 0.8(3) . . . . ? C3 C11 C16 C15 178.98(16) . . . . ? C9 N8 C18 C41 -99.00(18) . . . . ? C7 N8 C18 C41 106.41(17) . . . . ? C29 N21 C22 C27 0.25(17) . . . . ? C29 N21 C22 C23 178.88(16) . . . . ? N21 C22 C23 C24 178.93(15) . . . . ? C27 C22 C23 C24 -2.6(2) . . . . ? N21 C22 C23 C31 -3.5(3) . . . . ? C27 C22 C23 C31 174.97(14) . . . . ? C22 C23 C24 C25 2.2(2) . . . . ? C31 C23 C24 C25 -175.33(15) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C23 C24 C25 C30 -179.50(15) . . . . ? C24 C25 C26 C27 -2.4(2) . . . . ? C30 C25 C26 C27 177.36(14) . . . . ? C29 N28 C27 C26 -179.26(16) . . . . ? C38 N28 C27 C26 -20.6(3) . . . . ? C29 N28 C27 C22 0.39(16) . . . . ? C38 N28 C27 C22 159.02(14) . . . . ? C25 C26 C27 N28 -178.35(15) . . . . ? C25 C26 C27 C22 2.1(2) . . . . ? N21 C22 C27 N28 -0.41(17) . . . . ? C23 C22 C27 N28 -179.18(13) . . . . ? N21 C22 C27 C26 179.28(14) . . . . ? C23 C22 C27 C26 0.5(2) . . . . ? C22 N21 C29 N28 0.01(18) . . . . ? C22 N21 C29 C9 179.21(14) . . . . ? C27 N28 C29 N21 -0.27(18) . . . . ? C38 N28 C29 N21 -158.94(14) . . . . ? C27 N28 C29 C9 -179.50(14) . . . . ? C38 N28 C29 C9 21.8(2) . . . . ? N1 C9 C29 N21 39.9(2) . . . . ? N8 C9 C29 N21 -141.33(16) . . . . ? N1 C9 C29 N28 -140.91(16) . . . . ? N8 C9 C29 N28 37.8(2) . . . . ? C24 C23 C31 C32 -152.89(16) . . . . ? C22 C23 C31 C32 29.7(2) . . . . ? C24 C23 C31 C36 27.7(2) . . . . ? C22 C23 C31 C36 -149.64(16) . . . . ? C36 C31 C32 C33 -2.1(2) . . . . ? C23 C31 C32 C33 178.54(15) . . . . ? C31 C32 C33 C34 0.9(3) . . . . ? C37 O34 C34 C33 -2.2(2) . . . . ? C37 O34 C34 C35 177.84(15) . . . . ? C32 C33 C34 O34 -179.07(15) . . . . ? C32 C33 C34 C35 0.9(3) . . . . ? O34 C34 C35 C36 178.53(16) . . . . ? C33 C34 C35 C36 -1.4(3) . . . . ? C34 C35 C36 C31 0.2(3) . . . . ? C32 C31 C36 C35 1.5(3) . . . . ? C23 C31 C36 C35 -179.08(16) . . . . ? C29 N28 C38 C46 -100.76(18) . . . . ? C27 N28 C38 C46 104.69(18) . . . . ? N8 C18 C41 C42 -133.85(16) . . . . ? N8 C18 C41 C46 51.4(2) . . . . ? C46 C41 C42 C43 -0.6(2) . . . . ? C18 C41 C42 C43 -175.57(16) . . . . ? C41 C42 C43 C44 -0.2(3) . . . . ? C42 C43 C44 C45 0.6(3) . . . . ? C43 C44 C45 C46 -0.3(3) . . . . ? C44 C45 C46 C41 -0.5(2) . . . . ? C44 C45 C46 C38 -175.60(16) . . . . ? C42 C41 C46 C45 0.9(2) . . . . ? C18 C41 C46 C45 175.57(14) . . . . ? C42 C41 C46 C38 175.76(14) . . . . ? C18 C41 C46 C38 -9.6(2) . . . . ? N28 C38 C46 C45 -132.16(15) . . . . ? N28 C38 C46 C41 52.9(2) . . . . ? # End of CIF ============================================================ # Attachment '3b.cif' data_SG0719 _database_code_depnum_ccdc_archive 'CCDC 710115' _audit_creation_method SHELXL-97 _audit_creation_date 07-05-15 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C42 H40 N4 O2, C3 H6 O' _chemical_formula_sum 'C45 H46 N4 O3' _chemical_formula_weight 690.88 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 180 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 184 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 16 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 12 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 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 21.4622(3) _cell_length_b 7.4031(1) _cell_length_c 23.7326(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.2256(9) _cell_angle_gamma 90.00 _cell_volume 3760.55(9) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 9257 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.0767 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: dichloromethane / acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.414(1) Frames collected: 573 Seconds exposure per frame: 25 Degrees rotation per frame: 1.4 Crystal-Detector distance (mm): 35.5 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 86943 _diffrn_reflns_av_R_equivalents 0.1080 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 8633 _reflns_number_gt 5874 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1189P)^2^+1.4731P] 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 0.033(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8633 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1144 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.2173 _refine_ls_wR_factor_gt 0.1898 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.662 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.122 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 O14 O 0.61653(9) -0.0028(3) 0.80927(8) 0.0454(5) Uani 1 1 d . . . O34 O 0.22784(8) 0.6561(2) 0.49448(7) 0.0309(4) Uani 1 1 d . . . N1 N 0.32143(8) 0.2268(2) 0.83754(7) 0.0187(4) Uani 1 1 d . . . N8 N 0.24767(8) 0.3693(2) 0.88398(7) 0.0166(4) Uani 1 1 d . . . N21 N 0.20683(8) 0.2962(2) 0.74181(7) 0.0177(4) Uani 1 1 d . . . N28 N 0.15771(8) 0.1593(2) 0.81085(7) 0.0165(4) Uani 1 1 d . . . C2 C 0.34785(10) 0.2944(3) 0.88885(9) 0.0173(5) Uani 1 1 d . . . C3 C 0.40955(10) 0.2851(3) 0.91254(9) 0.0197(5) Uani 1 1 d . . . C4 C 0.42128(10) 0.3670(3) 0.96507(9) 0.0226(5) Uani 1 1 d . . . H4 H 0.4627 0.3623 0.9822 0.027 Uiso 1 1 calc R . . C5 C 0.37546(10) 0.4565(3) 0.99434(9) 0.0224(5) Uani 1 1 d . . . C6 C 0.31469(10) 0.4645(3) 0.97070(9) 0.0189(5) Uani 1 1 d . . . H6 H 0.2827 0.5231 0.9895 0.023 Uiso 1 1 calc R . . C7 C 0.30226(9) 0.3832(3) 0.91825(9) 0.0160(4) Uani 1 1 d . . . C9 C 0.26248(10) 0.2755(3) 0.83690(9) 0.0173(5) Uani 1 1 d . . . C10 C 0.39312(12) 0.5446(4) 1.05056(10) 0.0311(6) Uani 1 1 d . . . H101 H 0.4102 0.6652 1.0444 0.047 Uiso 1 1 calc R . . H102 H 0.4246 0.4708 1.0718 0.047 Uiso 1 1 calc R . . H103 H 0.3560 0.5551 1.0720 0.047 Uiso 1 1 calc R . . C11 C 0.46148(10) 0.1992(3) 0.88342(9) 0.0218(5) Uani 1 1 d . . . C12 C 0.48226(11) 0.0254(3) 0.89803(10) 0.0247(5) Uani 1 1 d . . . C13 C 0.53445(11) -0.0460(3) 0.87373(11) 0.0305(6) Uani 1 1 d . . . H13 H 0.5490 -0.1636 0.8840 0.037 Uiso 1 1 calc R . . C14 C 0.56483(11) 0.0535(4) 0.83504(10) 0.0303(6) Uani 1 1 d . . . C15 C 0.54278(11) 0.2233(3) 0.81918(10) 0.0298(6) Uani 1 1 d . . . H15 H 0.5632 0.2898 0.7917 0.036 Uiso 1 1 calc R . . C16 C 0.49166(11) 0.2976(3) 0.84260(10) 0.0252(5) Uani 1 1 d . . . C17 C 0.44829(12) -0.0888(4) 0.93861(12) 0.0359(6) Uani 1 1 d . . . H171 H 0.4489 -0.0278 0.9753 0.054 Uiso 1 1 calc R . . H172 H 0.4690 -0.2064 0.9432 0.054 Uiso 1 1 calc R . . H173 H 0.4049 -0.1062 0.9236 0.054 Uiso 1 1 calc R . . C18 C 0.64057(16) -0.1779(5) 0.82270(17) 0.0641(11) Uani 1 1 d . . . H181 H 0.6498 -0.1877 0.8636 0.096 Uiso 1 1 calc R . . H182 H 0.6790 -0.1973 0.8036 0.096 Uiso 1 1 calc R . . H183 H 0.6095 -0.2692 0.8101 0.096 Uiso 1 1 calc R . . C19 C 0.46862(13) 0.4817(4) 0.82420(11) 0.0368(6) Uani 1 1 d . . . H191 H 0.4981 0.5362 0.7996 0.055 Uiso 1 1 calc R . . H192 H 0.4652 0.5583 0.8575 0.055 Uiso 1 1 calc R . . H193 H 0.4275 0.4705 0.8035 0.055 Uiso 1 1 calc R . . C22 C 0.14636(9) 0.2511(3) 0.72209(9) 0.0160(4) Uani 1 1 d . . . C23 C 0.11481(10) 0.2876(3) 0.66927(9) 0.0186(5) Uani 1 1 d . . . C24 C 0.05328(10) 0.2301(3) 0.66214(9) 0.0210(5) Uani 1 1 d . . . H24 H 0.0306 0.2543 0.6271 0.025 Uiso 1 1 calc R . . C25 C 0.02251(10) 0.1377(3) 0.70400(9) 0.0194(5) Uani 1 1 d . . . C26 C 0.05380(10) 0.1032(3) 0.75606(9) 0.0179(5) Uani 1 1 d . . . H26 H 0.0342 0.0410 0.7849 0.021 Uiso 1 1 calc R . . C27 C 0.11517(10) 0.1637(3) 0.76427(8) 0.0157(4) Uani 1 1 d . . . C29 C 0.21134(10) 0.2386(3) 0.79422(9) 0.0168(5) Uani 1 1 d . . . C30 C -0.04423(11) 0.0789(4) 0.69160(10) 0.0294(6) Uani 1 1 d . . . H301 H -0.0560 -0.0042 0.7212 0.044 Uiso 1 1 calc R . . H302 H -0.0485 0.0176 0.6549 0.044 Uiso 1 1 calc R . . H303 H -0.0716 0.1849 0.6906 0.044 Uiso 1 1 calc R . . C31 C 0.14608(10) 0.3845(3) 0.62382(8) 0.0179(5) Uani 1 1 d . . . C32 C 0.19242(10) 0.2975(3) 0.59556(9) 0.0200(5) Uani 1 1 d . . . C33 C 0.22107(11) 0.3862(3) 0.55239(9) 0.0225(5) Uani 1 1 d . . . H33 H 0.2527 0.3272 0.5333 0.027 Uiso 1 1 calc R . . C34 C 0.20316(11) 0.5601(3) 0.53767(9) 0.0216(5) Uani 1 1 d . . . C35 C 0.15784(11) 0.6477(3) 0.56591(9) 0.0230(5) Uani 1 1 d . . . H35 H 0.1462 0.7675 0.5553 0.028 Uiso 1 1 calc R . . C36 C 0.12910(10) 0.5639(3) 0.60941(9) 0.0206(5) Uani 1 1 d . . . C37 C 0.21245(12) 0.1081(3) 0.61088(10) 0.0286(6) Uani 1 1 d . . . H371 H 0.2330 0.0540 0.5794 0.043 Uiso 1 1 calc R . . H372 H 0.1757 0.0360 0.6186 0.043 Uiso 1 1 calc R . . H373 H 0.2417 0.1107 0.6446 0.043 Uiso 1 1 calc R . . C38 C 0.28051(13) 0.5792(3) 0.47060(11) 0.0332(6) Uani 1 1 d . . . H381 H 0.3145 0.5643 0.5001 0.050 Uiso 1 1 calc R . . H382 H 0.2942 0.6591 0.4410 0.050 Uiso 1 1 calc R . . H383 H 0.2691 0.4612 0.4542 0.050 Uiso 1 1 calc R . . C39 C 0.08176(12) 0.6666(3) 0.64034(10) 0.0297(6) Uani 1 1 d . . . H391 H 0.0828 0.7944 0.6297 0.045 Uiso 1 1 calc R . . H392 H 0.0916 0.6550 0.6812 0.045 Uiso 1 1 calc R . . H393 H 0.0400 0.6175 0.6304 0.045 Uiso 1 1 calc R . . C41 C 0.18917(9) 0.4648(3) 0.89080(9) 0.0189(5) Uani 1 1 d . . . H411 H 0.1695 0.4943 0.8529 0.023 Uiso 1 1 calc R . . H412 H 0.1989 0.5803 0.9106 0.023 Uiso 1 1 calc R . . C42 C 0.14252(10) 0.3622(3) 0.92306(9) 0.0189(5) Uani 1 1 d . . . C43 C 0.11616(11) 0.4529(3) 0.96679(9) 0.0265(5) Uani 1 1 d . . . H43 H 0.1287 0.5737 0.9751 0.032 Uiso 1 1 calc R . . C44 C 0.07237(12) 0.3725(4) 0.99843(10) 0.0357(6) Uani 1 1 d . . . H44 H 0.0550 0.4373 1.0281 0.043 Uiso 1 1 calc R . . C45 C 0.05422(13) 0.1988(4) 0.98663(11) 0.0394(7) Uani 1 1 d . . . H45 H 0.0247 0.1415 1.0086 0.047 Uiso 1 1 calc R . . C46 C 0.07896(12) 0.1058(4) 0.94238(10) 0.0309(6) Uani 1 1 d . . . H46 H 0.0655 -0.0142 0.9342 0.037 Uiso 1 1 calc R . . C47 C 0.12295(10) 0.1848(3) 0.90994(9) 0.0203(5) Uani 1 1 d . . . C48 C 0.15018(11) 0.0700(3) 0.86492(9) 0.0209(5) Uani 1 1 d . . . H481 H 0.1916 0.0256 0.8800 0.025 Uiso 1 1 calc R . . H482 H 0.1230 -0.0367 0.8578 0.025 Uiso 1 1 calc R . . O1 O 0.21835(17) 0.7715(3) 0.81184(17) 0.1212(16) Uani 1 1 d . . . C51 C 0.3241(2) 0.7489(6) 0.80236(17) 0.0803(13) Uani 1 1 d . . . H511 H 0.3448 0.8658 0.7988 0.120 Uiso 1 1 calc R . . H512 H 0.3454 0.6573 0.7810 0.120 Uiso 1 1 calc R . . H513 H 0.3255 0.7140 0.8423 0.120 Uiso 1 1 calc R . . C52 C 0.25914(17) 0.7632(4) 0.77998(16) 0.0560(10) Uani 1 1 d . . . C53 C 0.2465(2) 0.7625(6) 0.71729(19) 0.0845(14) Uani 1 1 d . . . H531 H 0.2439 0.6376 0.7037 0.127 Uiso 1 1 calc R . . H532 H 0.2804 0.8251 0.6999 0.127 Uiso 1 1 calc R . . H533 H 0.2069 0.8245 0.7072 0.127 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 O14 0.0327(11) 0.0529(12) 0.0533(12) 0.0107(10) 0.0221(9) 0.0188(10) O34 0.0385(10) 0.0255(9) 0.0313(9) 0.0082(7) 0.0199(8) 0.0018(8) N1 0.0142(9) 0.0240(10) 0.0177(9) -0.0009(7) 0.0002(7) -0.0003(8) N8 0.0103(8) 0.0219(9) 0.0176(9) -0.0029(7) 0.0002(7) 0.0012(7) N21 0.0138(9) 0.0233(10) 0.0161(9) -0.0007(7) 0.0009(7) -0.0005(7) N28 0.0143(9) 0.0216(9) 0.0137(9) 0.0012(7) 0.0006(7) -0.0026(7) C2 0.0154(11) 0.0192(10) 0.0172(10) 0.0007(8) 0.0000(8) 0.0010(9) C3 0.0144(11) 0.0245(11) 0.0201(11) 0.0028(9) 0.0001(8) 0.0010(9) C4 0.0151(11) 0.0278(12) 0.0240(12) -0.0011(9) -0.0052(9) 0.0005(9) C5 0.0209(12) 0.0249(11) 0.0213(11) 0.0006(9) 0.0009(9) -0.0016(9) C6 0.0188(11) 0.0203(11) 0.0178(11) -0.0005(8) 0.0015(8) 0.0005(9) C7 0.0127(10) 0.0165(10) 0.0186(10) 0.0013(8) -0.0007(8) -0.0006(8) C9 0.0141(10) 0.0217(11) 0.0163(10) 0.0008(8) 0.0018(8) 0.0005(9) C10 0.0270(13) 0.0420(15) 0.0235(12) -0.0069(11) -0.0030(10) -0.0011(11) C11 0.0120(10) 0.0295(12) 0.0234(12) -0.0031(9) -0.0026(8) 0.0007(9) C12 0.0173(11) 0.0295(12) 0.0274(12) -0.0001(10) 0.0024(9) 0.0006(10) C13 0.0229(13) 0.0304(13) 0.0386(14) 0.0045(11) 0.0057(10) 0.0086(11) C14 0.0173(12) 0.0417(15) 0.0324(13) -0.0011(11) 0.0050(10) 0.0076(11) C15 0.0227(13) 0.0384(14) 0.0290(13) 0.0036(11) 0.0073(10) 0.0034(11) C16 0.0201(12) 0.0322(13) 0.0227(12) -0.0008(10) -0.0012(9) 0.0017(10) C17 0.0301(14) 0.0311(14) 0.0477(16) 0.0075(12) 0.0115(12) 0.0049(11) C18 0.050(2) 0.063(2) 0.084(3) 0.0165(19) 0.0357(19) 0.0357(18) C19 0.0376(15) 0.0369(15) 0.0369(15) 0.0104(12) 0.0102(12) 0.0067(12) C22 0.0123(10) 0.0186(10) 0.0176(10) -0.0018(8) 0.0026(8) -0.0013(8) C23 0.0181(11) 0.0206(11) 0.0172(11) 0.0010(8) 0.0016(8) -0.0028(9) C24 0.0188(11) 0.0259(11) 0.0179(11) 0.0014(9) -0.0018(8) -0.0031(9) C25 0.0145(11) 0.0225(11) 0.0212(11) -0.0008(9) 0.0002(8) -0.0035(9) C26 0.0171(11) 0.0191(10) 0.0181(11) 0.0008(8) 0.0046(8) -0.0041(9) C27 0.0157(10) 0.0168(10) 0.0148(10) -0.0022(8) 0.0010(8) 0.0018(8) C29 0.0137(10) 0.0196(10) 0.0174(11) -0.0015(8) 0.0026(8) -0.0013(9) C30 0.0184(12) 0.0390(14) 0.0304(13) 0.0047(11) -0.0012(10) -0.0108(11) C31 0.0162(11) 0.0232(11) 0.0141(10) 0.0006(8) -0.0007(8) -0.0036(9) C32 0.0191(11) 0.0212(11) 0.0198(11) 0.0002(9) 0.0007(9) -0.0043(9) C33 0.0232(12) 0.0224(11) 0.0227(12) -0.0013(9) 0.0068(9) -0.0014(10) C34 0.0245(12) 0.0231(11) 0.0180(11) 0.0023(9) 0.0063(9) -0.0042(10) C35 0.0277(13) 0.0215(11) 0.0199(11) 0.0012(9) 0.0024(9) 0.0013(10) C36 0.0194(11) 0.0247(11) 0.0174(11) 0.0003(9) 0.0004(8) -0.0034(9) C37 0.0326(14) 0.0245(12) 0.0297(13) 0.0040(10) 0.0093(10) 0.0017(11) C38 0.0385(15) 0.0319(13) 0.0317(14) 0.0014(11) 0.0203(11) -0.0028(12) C39 0.0294(13) 0.0328(13) 0.0280(13) 0.0036(10) 0.0086(10) 0.0058(11) C41 0.0122(10) 0.0220(11) 0.0224(11) -0.0001(9) 0.0003(8) 0.0027(9) C42 0.0122(10) 0.0289(12) 0.0150(10) 0.0011(9) -0.0026(8) 0.0035(9) C43 0.0221(12) 0.0370(14) 0.0204(12) -0.0064(10) 0.0008(9) 0.0025(11) C44 0.0319(14) 0.0523(17) 0.0241(13) -0.0095(12) 0.0101(11) -0.0013(13) C45 0.0355(15) 0.0578(18) 0.0268(14) -0.0009(12) 0.0147(11) -0.0142(14) C46 0.0316(14) 0.0389(14) 0.0228(12) 0.0005(11) 0.0070(10) -0.0094(12) C47 0.0171(11) 0.0288(12) 0.0149(11) 0.0022(9) -0.0005(8) 0.0002(9) C48 0.0240(12) 0.0225(11) 0.0159(11) 0.0034(9) 0.0004(9) -0.0023(9) O1 0.149(3) 0.0399(14) 0.194(4) 0.0216(17) 0.141(3) 0.0225(16) C51 0.098(3) 0.085(3) 0.057(2) -0.007(2) 0.001(2) 0.040(3) C52 0.069(2) 0.0265(15) 0.078(2) 0.0226(15) 0.0428(19) 0.0230(15) C53 0.079(3) 0.077(3) 0.093(3) 0.038(2) -0.021(2) -0.002(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 O14 C14 1.371(3) . ? O14 C18 1.422(4) . ? O34 C34 1.384(3) . ? O34 C38 1.420(3) . ? N1 C9 1.315(3) . ? N1 C2 1.397(3) . ? N8 C9 1.372(3) . ? N8 C7 1.380(3) . ? N8 C41 1.460(3) . ? N21 C29 1.312(3) . ? N21 C22 1.388(3) . ? N28 C29 1.376(3) . ? N28 C27 1.381(3) . ? N28 C48 1.463(3) . ? C2 C3 1.402(3) . ? C2 C7 1.406(3) . ? C3 C4 1.393(3) . ? C3 C11 1.496(3) . ? C4 C5 1.410(3) . ? C4 H4 0.9500 . ? C5 C6 1.383(3) . ? C5 C10 1.508(3) . ? C6 C7 1.391(3) . ? C6 H6 0.9500 . ? C9 C29 1.463(3) . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 C12 1.397(3) . ? C11 C16 1.408(3) . ? C12 C13 1.401(3) . ? C12 C17 1.509(3) . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(4) . ? C15 C16 1.380(3) . ? C15 H15 0.9500 . ? C16 C19 1.504(3) . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C22 C27 1.403(3) . ? C22 C23 1.407(3) . ? C23 C24 1.386(3) . ? C23 C31 1.495(3) . ? C24 C25 1.410(3) . ? C24 H24 0.9500 . ? C25 C26 1.386(3) . ? C25 C30 1.505(3) . ? C26 C27 1.391(3) . ? C26 H26 0.9500 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 C32 1.397(3) . ? C31 C36 1.413(3) . ? C32 C33 1.397(3) . ? C32 C37 1.503(3) . ? C33 C34 1.381(3) . ? C33 H33 0.9500 . ? C34 C35 1.383(3) . ? C35 C36 1.387(3) . ? C35 H35 0.9500 . ? C36 C39 1.503(3) . ? C37 H371 0.9800 . ? C37 H372 0.9800 . ? C37 H373 0.9800 . ? C38 H381 0.9800 . ? C38 H382 0.9800 . ? C38 H383 0.9800 . ? C39 H391 0.9800 . ? C39 H392 0.9800 . ? C39 H393 0.9800 . ? C41 C42 1.509(3) . ? C41 H411 0.9900 . ? C41 H412 0.9900 . ? C42 C43 1.391(3) . ? C42 C47 1.407(3) . ? C43 C44 1.380(3) . ? C43 H43 0.9500 . ? C44 C45 1.367(4) . ? C44 H44 0.9500 . ? C45 C46 1.393(4) . ? C45 H45 0.9500 . ? C46 C47 1.390(3) . ? C46 H46 0.9500 . ? C47 C48 1.515(3) . ? C48 H481 0.9900 . ? C48 H482 0.9900 . ? O1 C52 1.200(4) . ? C51 C52 1.458(5) . ? C51 H511 0.9800 . ? C51 H512 0.9800 . ? C51 H513 0.9800 . ? C52 C53 1.493(5) . ? C53 H531 0.9800 . ? C53 H532 0.9800 . ? C53 H533 0.9800 . ? 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 C14 O14 C18 118.0(2) . . ? C34 O34 C38 116.66(18) . . ? C9 N1 C2 103.91(17) . . ? C9 N8 C7 106.28(17) . . ? C9 N8 C41 126.00(17) . . ? C7 N8 C41 126.72(17) . . ? C29 N21 C22 104.09(17) . . ? C29 N28 C27 106.13(16) . . ? C29 N28 C48 126.40(18) . . ? C27 N28 C48 127.13(18) . . ? N1 C2 C3 129.97(19) . . ? N1 C2 C7 110.32(18) . . ? C3 C2 C7 119.71(19) . . ? C4 C3 C2 116.15(19) . . ? C4 C3 C11 120.46(19) . . ? C2 C3 C11 123.36(19) . . ? C3 C4 C5 124.0(2) . . ? C3 C4 H4 118.0 . . ? C5 C4 H4 118.0 . . ? C6 C5 C4 119.4(2) . . ? C6 C5 C10 120.6(2) . . ? C4 C5 C10 120.0(2) . . ? C5 C6 C7 117.2(2) . . ? C5 C6 H6 121.4 . . ? C7 C6 H6 121.4 . . ? N8 C7 C6 131.19(19) . . ? N8 C7 C2 105.31(17) . . ? C6 C7 C2 123.50(19) . . ? N1 C9 N8 114.18(18) . . ? N1 C9 C29 128.98(19) . . ? N8 C9 C29 116.82(18) . . ? C5 C10 H101 109.5 . . ? C5 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C5 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C12 C11 C16 119.5(2) . . ? C12 C11 C3 120.8(2) . . ? C16 C11 C3 119.6(2) . . ? C11 C12 C13 119.7(2) . . ? C11 C12 C17 120.9(2) . . ? C13 C12 C17 119.3(2) . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? O14 C14 C13 124.9(2) . . ? O14 C14 C15 115.2(2) . . ? C13 C14 C15 119.8(2) . . ? C16 C15 C14 121.2(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 119.4(2) . . ? C15 C16 C19 119.9(2) . . ? C11 C16 C19 120.7(2) . . ? C12 C17 H171 109.5 . . ? C12 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C12 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? O14 C18 H181 109.5 . . ? O14 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? O14 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C16 C19 H191 109.5 . . ? C16 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C16 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? N21 C22 C27 110.74(18) . . ? N21 C22 C23 129.15(19) . . ? C27 C22 C23 120.07(19) . . ? C24 C23 C22 116.21(19) . . ? C24 C23 C31 122.26(19) . . ? C22 C23 C31 121.53(19) . . ? C23 C24 C25 123.7(2) . . ? C23 C24 H24 118.2 . . ? C25 C24 H24 118.2 . . ? C26 C25 C24 119.75(19) . . ? C26 C25 C30 120.84(19) . . ? C24 C25 C30 119.40(19) . . ? C25 C26 C27 117.21(19) . . ? C25 C26 H26 121.4 . . ? C27 C26 H26 121.4 . . ? N28 C27 C26 131.88(19) . . ? N28 C27 C22 105.08(17) . . ? C26 C27 C22 123.03(19) . . ? N21 C29 N28 113.96(18) . . ? N21 C29 C9 126.52(19) . . ? N28 C29 C9 118.79(18) . . ? C25 C30 H301 109.5 . . ? C25 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C25 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C32 C31 C36 119.81(19) . . ? C32 C31 C23 119.89(19) . . ? C36 C31 C23 120.29(19) . . ? C33 C32 C31 120.2(2) . . ? C33 C32 C37 118.8(2) . . ? C31 C32 C37 120.99(19) . . ? C34 C33 C32 119.6(2) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 120.5(2) . . ? C33 C34 O34 123.5(2) . . ? C35 C34 O34 116.04(19) . . ? C34 C35 C36 121.2(2) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C35 C36 C31 118.7(2) . . ? C35 C36 C39 119.4(2) . . ? C31 C36 C39 121.9(2) . . ? C32 C37 H371 109.5 . . ? C32 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? C32 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? O34 C38 H381 109.5 . . ? O34 C38 H382 109.5 . . ? H381 C38 H382 109.5 . . ? O34 C38 H383 109.5 . . ? H381 C38 H383 109.5 . . ? H382 C38 H383 109.5 . . ? C36 C39 H391 109.5 . . ? C36 C39 H392 109.5 . . ? H391 C39 H392 109.5 . . ? C36 C39 H393 109.5 . . ? H391 C39 H393 109.5 . . ? H392 C39 H393 109.5 . . ? N8 C41 C42 114.86(17) . . ? N8 C41 H411 108.6 . . ? C42 C41 H411 108.6 . . ? N8 C41 H412 108.6 . . ? C42 C41 H412 108.6 . . ? H411 C41 H412 107.5 . . ? C43 C42 C47 119.0(2) . . ? C43 C42 C41 117.2(2) . . ? C47 C42 C41 123.77(19) . . ? C44 C43 C42 121.9(2) . . ? C44 C43 H43 119.0 . . ? C42 C43 H43 119.0 . . ? C45 C44 C43 119.3(2) . . ? C45 C44 H44 120.3 . . ? C43 C44 H44 120.3 . . ? C44 C45 C46 120.1(2) . . ? C44 C45 H45 120.0 . . ? C46 C45 H45 120.0 . . ? C47 C46 C45 121.4(2) . . ? C47 C46 H46 119.3 . . ? C45 C46 H46 119.3 . . ? C46 C47 C42 118.3(2) . . ? C46 C47 C48 117.9(2) . . ? C42 C47 C48 123.70(19) . . ? N28 C48 C47 116.02(18) . . ? N28 C48 H481 108.3 . . ? C47 C48 H481 108.3 . . ? N28 C48 H482 108.3 . . ? C47 C48 H482 108.3 . . ? H481 C48 H482 107.4 . . ? C52 C51 H511 109.5 . . ? C52 C51 H512 109.5 . . ? H511 C51 H512 109.5 . . ? C52 C51 H513 109.5 . . ? H511 C51 H513 109.5 . . ? H512 C51 H513 109.5 . . ? O1 C52 C51 119.8(4) . . ? O1 C52 C53 122.7(4) . . ? C51 C52 C53 117.5(3) . . ? C52 C53 H531 109.5 . . ? C52 C53 H532 109.5 . . ? H531 C53 H532 109.5 . . ? C52 C53 H533 109.5 . . ? H531 C53 H533 109.5 . . ? H532 C53 H533 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 C9 N1 C2 C3 -179.6(2) . . . . ? C9 N1 C2 C7 0.3(2) . . . . ? N1 C2 C3 C4 180.0(2) . . . . ? C7 C2 C3 C4 0.1(3) . . . . ? N1 C2 C3 C11 2.1(4) . . . . ? C7 C2 C3 C11 -177.8(2) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C11 C3 C4 C5 177.6(2) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C3 C4 C5 C10 -178.7(2) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C10 C5 C6 C7 178.7(2) . . . . ? C9 N8 C7 C6 179.7(2) . . . . ? C41 N8 C7 C6 10.7(4) . . . . ? C9 N8 C7 C2 0.0(2) . . . . ? C41 N8 C7 C2 -169.00(19) . . . . ? C5 C6 C7 N8 -179.5(2) . . . . ? C5 C6 C7 C2 0.2(3) . . . . ? N1 C2 C7 N8 -0.2(2) . . . . ? C3 C2 C7 N8 179.72(19) . . . . ? N1 C2 C7 C6 -179.96(19) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C2 N1 C9 N8 -0.3(2) . . . . ? C2 N1 C9 C29 -178.3(2) . . . . ? C7 N8 C9 N1 0.2(2) . . . . ? C41 N8 C9 N1 169.33(19) . . . . ? C7 N8 C9 C29 178.48(18) . . . . ? C41 N8 C9 C29 -12.4(3) . . . . ? C4 C3 C11 C12 81.1(3) . . . . ? C2 C3 C11 C12 -101.1(3) . . . . ? C4 C3 C11 C16 -96.0(3) . . . . ? C2 C3 C11 C16 81.8(3) . . . . ? C16 C11 C12 C13 2.7(3) . . . . ? C3 C11 C12 C13 -174.4(2) . . . . ? C16 C11 C12 C17 -175.8(2) . . . . ? C3 C11 C12 C17 7.1(3) . . . . ? C11 C12 C13 C14 -0.8(4) . . . . ? C17 C12 C13 C14 177.7(2) . . . . ? C18 O14 C14 C13 0.8(4) . . . . ? C18 O14 C14 C15 -178.5(3) . . . . ? C12 C13 C14 O14 179.3(2) . . . . ? C12 C13 C14 C15 -1.5(4) . . . . ? O14 C14 C15 C16 -178.9(2) . . . . ? C13 C14 C15 C16 1.8(4) . . . . ? C14 C15 C16 C11 0.1(4) . . . . ? C14 C15 C16 C19 -179.6(2) . . . . ? C12 C11 C16 C15 -2.4(3) . . . . ? C3 C11 C16 C15 174.8(2) . . . . ? C12 C11 C16 C19 177.4(2) . . . . ? C3 C11 C16 C19 -5.5(3) . . . . ? C29 N21 C22 C27 -0.4(2) . . . . ? C29 N21 C22 C23 176.8(2) . . . . ? N21 C22 C23 C24 -178.0(2) . . . . ? C27 C22 C23 C24 -1.0(3) . . . . ? N21 C22 C23 C31 1.4(3) . . . . ? C27 C22 C23 C31 178.49(19) . . . . ? C22 C23 C24 C25 -0.9(3) . . . . ? C31 C23 C24 C25 179.7(2) . . . . ? C23 C24 C25 C26 1.3(3) . . . . ? C23 C24 C25 C30 -179.2(2) . . . . ? C24 C25 C26 C27 0.2(3) . . . . ? C30 C25 C26 C27 -179.4(2) . . . . ? C29 N28 C27 C26 179.9(2) . . . . ? C48 N28 C27 C26 6.3(4) . . . . ? C29 N28 C27 C22 -1.3(2) . . . . ? C48 N28 C27 C22 -174.86(19) . . . . ? C25 C26 C27 N28 176.6(2) . . . . ? C25 C26 C27 C22 -2.0(3) . . . . ? N21 C22 C27 N28 1.1(2) . . . . ? C23 C22 C27 N28 -176.45(19) . . . . ? N21 C22 C27 C26 -179.94(19) . . . . ? C23 C22 C27 C26 2.5(3) . . . . ? C22 N21 C29 N28 -0.4(2) . . . . ? C22 N21 C29 C9 -170.4(2) . . . . ? C27 N28 C29 N21 1.2(2) . . . . ? C48 N28 C29 N21 174.77(19) . . . . ? C27 N28 C29 C9 171.96(18) . . . . ? C48 N28 C29 C9 -14.4(3) . . . . ? N1 C9 C29 N21 -64.3(3) . . . . ? N8 C9 C29 N21 117.7(2) . . . . ? N1 C9 C29 N28 126.1(2) . . . . ? N8 C9 C29 N28 -51.8(3) . . . . ? C24 C23 C31 C32 -109.1(3) . . . . ? C22 C23 C31 C32 71.5(3) . . . . ? C24 C23 C31 C36 71.1(3) . . . . ? C22 C23 C31 C36 -108.3(2) . . . . ? C36 C31 C32 C33 -1.3(3) . . . . ? C23 C31 C32 C33 178.90(19) . . . . ? C36 C31 C32 C37 178.6(2) . . . . ? C23 C31 C32 C37 -1.2(3) . . . . ? C31 C32 C33 C34 -0.2(3) . . . . ? C37 C32 C33 C34 179.9(2) . . . . ? C32 C33 C34 C35 1.0(3) . . . . ? C32 C33 C34 O34 -178.2(2) . . . . ? C38 O34 C34 C33 -9.6(3) . . . . ? C38 O34 C34 C35 171.1(2) . . . . ? C33 C34 C35 C36 -0.2(3) . . . . ? O34 C34 C35 C36 179.1(2) . . . . ? C34 C35 C36 C31 -1.3(3) . . . . ? C34 C35 C36 C39 177.8(2) . . . . ? C32 C31 C36 C35 2.0(3) . . . . ? C23 C31 C36 C35 -178.16(19) . . . . ? C32 C31 C36 C39 -177.0(2) . . . . ? C23 C31 C36 C39 2.8(3) . . . . ? C9 N8 C41 C42 98.9(2) . . . . ? C7 N8 C41 C42 -94.2(2) . . . . ? N8 C41 C42 C43 130.5(2) . . . . ? N8 C41 C42 C47 -51.9(3) . . . . ? C47 C42 C43 C44 1.4(3) . . . . ? C41 C42 C43 C44 179.1(2) . . . . ? C42 C43 C44 C45 0.0(4) . . . . ? C43 C44 C45 C46 -1.2(4) . . . . ? C44 C45 C46 C47 1.0(4) . . . . ? C45 C46 C47 C42 0.4(4) . . . . ? C45 C46 C47 C48 176.5(2) . . . . ? C43 C42 C47 C46 -1.6(3) . . . . ? C41 C42 C47 C46 -179.1(2) . . . . ? C43 C42 C47 C48 -177.4(2) . . . . ? C41 C42 C47 C48 5.1(3) . . . . ? C29 N28 C48 C47 96.1(2) . . . . ? C27 N28 C48 C47 -91.6(3) . . . . ? C46 C47 C48 N28 138.4(2) . . . . ? C42 C47 C48 N28 -45.8(3) . . . . ? # End of CIF ============================================================ # Attachment '3c.cif' data_SG0625 _database_code_depnum_ccdc_archive 'CCDC 710116' _audit_creation_method SHELXL-97 _audit_creation_date 06-06-29 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C33 H30 N4 O2, C H2 Cl2' _chemical_formula_sum 'C34 H32 Cl2 N4 O2' _chemical_formula_weight 599.56 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 136 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 128 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 16 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 8 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 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 12.7522(2) _cell_length_b 22.9038(4) _cell_length_c 10.1324(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.7995(10) _cell_angle_gamma 90.00 _cell_volume 2833.11(9) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 83457 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_T_max 0.979 _exptl_special_details ; Solvent used: dichloromethane / hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.685(1) Frames collected: 0 Seconds exposure per frame: 45 Degrees rotation per frame: 0.0 Crystal-Detector distance (mm): 0.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 57343 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 6476 _reflns_number_gt 4378 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1283P)^2^+2.3765P] 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 0.029(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6474 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1080 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2237 _refine_ls_wR_factor_gt 0.1954 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.200 _refine_diff_density_min -1.066 _refine_diff_density_rms 0.115 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 O14 O 0.8808(2) 0.58089(9) 0.5608(2) 0.0412(6) Uani 1 1 d . . . O34 O 0.20089(17) 0.56906(9) -0.0526(2) 0.0367(5) Uani 1 1 d . . . N1 N 0.63484(19) 0.32129(10) 0.4077(2) 0.0267(5) Uani 1 1 d . . . N8 N 0.61770(19) 0.22644(10) 0.4569(2) 0.0259(5) Uani 1 1 d . . . N21 N 0.43739(19) 0.31507(10) 0.1806(2) 0.0263(5) Uani 1 1 d . . . N28 N 0.45422(19) 0.21743(10) 0.1646(2) 0.0276(5) Uani 1 1 d . . . C2 C 0.7117(2) 0.30731(12) 0.5314(3) 0.0254(6) Uani 1 1 d . . . C3 C 0.7923(2) 0.34226(12) 0.6214(3) 0.0261(6) Uani 1 1 d . . . C4 C 0.8583(2) 0.31469(13) 0.7386(3) 0.0297(6) Uani 1 1 d . . . H4 H 0.9135 0.3372 0.8007 0.036 Uiso 1 1 calc R . . C5 C 0.8483(2) 0.25573(13) 0.7707(3) 0.0296(6) Uani 1 1 d . . . C6 C 0.7686(2) 0.22171(13) 0.6827(3) 0.0283(6) Uani 1 1 d . . . H6 H 0.7598 0.1817 0.7020 0.034 Uiso 1 1 calc R . . C7 C 0.7016(2) 0.24834(12) 0.5642(3) 0.0260(6) Uani 1 1 d . . . C9 C 0.5812(2) 0.27210(12) 0.3663(3) 0.0257(6) Uani 1 1 d . . . C10 C 0.9255(3) 0.23042(14) 0.9006(3) 0.0353(7) Uani 1 1 d . . . H101 H 0.9062 0.2454 0.9812 0.053 Uiso 1 1 calc R . . H102 H 1.0009 0.2417 0.9067 0.053 Uiso 1 1 calc R . . H103 H 0.9195 0.1878 0.8982 0.053 Uiso 1 1 calc R . . C11 C 0.8103(2) 0.40503(12) 0.5986(3) 0.0274(6) Uani 1 1 d . . . C12 C 0.8141(2) 0.42656(13) 0.4712(3) 0.0305(6) Uani 1 1 d . . . H12 H 0.7997 0.4009 0.3944 0.037 Uiso 1 1 calc R . . C13 C 0.8386(3) 0.48471(13) 0.4539(3) 0.0318(6) Uani 1 1 d . . . H13 H 0.8426 0.4985 0.3670 0.038 Uiso 1 1 calc R . . C14 C 0.8570(2) 0.52233(12) 0.5655(3) 0.0315(6) Uani 1 1 d . . . C15 C 0.8508(3) 0.50209(13) 0.6923(3) 0.0342(7) Uani 1 1 d . . . H15 H 0.8622 0.5282 0.7680 0.041 Uiso 1 1 calc R . . C16 C 0.8282(2) 0.44441(13) 0.7081(3) 0.0314(6) Uani 1 1 d . . . H16 H 0.8245 0.4310 0.7954 0.038 Uiso 1 1 calc R . . C17 C 0.8793(3) 0.60434(14) 0.4305(3) 0.0438(8) Uani 1 1 d . . . H171 H 0.9400 0.5878 0.4015 0.066 Uiso 1 1 calc R . . H172 H 0.8872 0.6469 0.4377 0.066 Uiso 1 1 calc R . . H173 H 0.8097 0.5945 0.3624 0.066 Uiso 1 1 calc R . . C22 C 0.3593(2) 0.29517(12) 0.0634(3) 0.0254(6) Uani 1 1 d . . . C23 C 0.2760(2) 0.32492(12) -0.0367(3) 0.0275(6) Uani 1 1 d . . . C24 C 0.2100(2) 0.29072(13) -0.1414(3) 0.0298(6) Uani 1 1 d . . . H24 H 0.1532 0.3096 -0.2098 0.036 Uiso 1 1 calc R . . C25 C 0.2218(2) 0.23012(13) -0.1528(3) 0.0303(6) Uani 1 1 d . . . C26 C 0.3028(2) 0.20090(13) -0.0535(3) 0.0313(6) Uani 1 1 d . . . H26 H 0.3120 0.1599 -0.0578 0.038 Uiso 1 1 calc R . . C27 C 0.3698(2) 0.23409(12) 0.0525(3) 0.0274(6) Uani 1 1 d . . . C29 C 0.4917(2) 0.26825(12) 0.2389(3) 0.0252(6) Uani 1 1 d . . . C30 C 0.1463(3) 0.19719(15) -0.2719(3) 0.0378(7) Uani 1 1 d . . . H301 H 0.1712 0.1567 -0.2706 0.057 Uiso 1 1 calc R . . H302 H 0.1470 0.2157 -0.3589 0.057 Uiso 1 1 calc R . . H303 H 0.0717 0.1979 -0.2634 0.057 Uiso 1 1 calc R . . C31 C 0.2557(2) 0.38874(12) -0.0331(3) 0.0271(6) Uani 1 1 d . . . C32 C 0.3404(2) 0.42936(13) 0.0084(3) 0.0342(7) Uani 1 1 d . . . H32 H 0.4139 0.4160 0.0424 0.041 Uiso 1 1 calc R . . C33 C 0.3192(3) 0.48876(14) 0.0009(3) 0.0373(7) Uani 1 1 d . . . H33 H 0.3782 0.5156 0.0293 0.045 Uiso 1 1 calc R . . C34 C 0.2130(2) 0.50939(13) -0.0475(3) 0.0308(6) Uani 1 1 d . . . C35 C 0.1271(2) 0.47010(13) -0.0859(3) 0.0333(7) Uani 1 1 d . . . H35 H 0.0537 0.4836 -0.1174 0.040 Uiso 1 1 calc R . . C36 C 0.1495(2) 0.41047(13) -0.0778(3) 0.0321(7) Uani 1 1 d . . . H36 H 0.0901 0.3837 -0.1038 0.039 Uiso 1 1 calc R . . C37 C 0.0931(3) 0.59161(15) -0.1065(4) 0.0414(8) Uani 1 1 d . . . H371 H 0.0647 0.5812 -0.2042 0.062 Uiso 1 1 calc R . . H372 H 0.0947 0.6342 -0.0970 0.062 Uiso 1 1 calc R . . H373 H 0.0455 0.5750 -0.0555 0.062 Uiso 1 1 calc R . . C41 C 0.5838(2) 0.16521(12) 0.4388(3) 0.0307(6) Uani 1 1 d . . . H411 H 0.5085 0.1614 0.4463 0.037 Uiso 1 1 calc R . . H412 H 0.6331 0.1414 0.5127 0.037 Uiso 1 1 calc R . . C42 C 0.5876(3) 0.14269(13) 0.2995(3) 0.0324(7) Uani 1 1 d . . . H421 H 0.6510 0.1604 0.2769 0.039 Uiso 1 1 calc R . . H422 H 0.5990 0.0999 0.3055 0.039 Uiso 1 1 calc R . . C43 C 0.4857(3) 0.15567(13) 0.1849(3) 0.0360(7) Uani 1 1 d . . . H431 H 0.4957 0.1405 0.0979 0.043 Uiso 1 1 calc R . . H432 H 0.4241 0.1338 0.2028 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.57246(8) 0.49498(5) 0.25310(12) 0.0650(4) Uani 1 1 d . . . Cl2 Cl 0.39584(9) 0.46321(5) 0.36718(12) 0.0659(4) Uani 1 1 d . . . C44 C 0.5240(3) 0.44352(18) 0.3496(4) 0.0563(10) Uani 1 1 d . . . H441 H 0.5180 0.4050 0.3039 0.068 Uiso 1 1 calc R . . H442 H 0.5772 0.4399 0.4423 0.068 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 O14 0.0604(15) 0.0285(11) 0.0300(11) -0.0005(9) 0.0056(10) -0.0084(10) O34 0.0334(11) 0.0291(11) 0.0441(13) 0.0030(9) 0.0057(10) 0.0040(9) N1 0.0255(12) 0.0265(12) 0.0253(12) 0.0012(9) 0.0027(9) 0.0004(9) N8 0.0240(11) 0.0265(12) 0.0242(12) 0.0016(9) 0.0022(9) -0.0017(9) N21 0.0246(11) 0.0278(12) 0.0236(11) -0.0007(9) 0.0025(9) -0.0007(9) N28 0.0282(12) 0.0245(12) 0.0272(12) -0.0014(9) 0.0032(10) 0.0000(9) C2 0.0234(13) 0.0263(14) 0.0255(13) 0.0006(11) 0.0054(11) 0.0004(11) C3 0.0228(13) 0.0295(14) 0.0257(14) -0.0013(11) 0.0067(11) -0.0001(11) C4 0.0240(14) 0.0352(16) 0.0265(14) -0.0017(12) 0.0020(11) -0.0031(12) C5 0.0238(14) 0.0391(16) 0.0248(14) 0.0028(12) 0.0052(11) 0.0026(12) C6 0.0250(14) 0.0297(15) 0.0298(15) 0.0040(11) 0.0073(11) -0.0001(11) C7 0.0215(13) 0.0300(14) 0.0250(13) 0.0008(11) 0.0042(11) 0.0008(11) C9 0.0250(14) 0.0258(14) 0.0245(14) 0.0005(11) 0.0043(11) 0.0018(11) C10 0.0313(16) 0.0402(17) 0.0297(15) 0.0066(13) 0.0015(13) 0.0010(13) C11 0.0225(13) 0.0298(15) 0.0270(14) -0.0007(11) 0.0025(11) -0.0020(11) C12 0.0316(15) 0.0302(15) 0.0275(14) -0.0051(12) 0.0049(12) -0.0012(12) C13 0.0361(16) 0.0327(16) 0.0258(14) 0.0012(12) 0.0077(12) -0.0024(13) C14 0.0318(15) 0.0264(14) 0.0333(15) -0.0006(12) 0.0045(12) -0.0056(12) C15 0.0385(17) 0.0343(16) 0.0250(14) -0.0044(12) 0.0020(12) -0.0057(13) C16 0.0342(15) 0.0358(16) 0.0212(13) -0.0019(11) 0.0034(11) -0.0024(12) C17 0.059(2) 0.0334(17) 0.0348(17) 0.0054(13) 0.0064(15) -0.0107(15) C22 0.0250(13) 0.0259(14) 0.0242(13) -0.0007(10) 0.0055(11) -0.0029(11) C23 0.0263(14) 0.0321(15) 0.0238(14) 0.0017(11) 0.0068(11) -0.0023(11) C24 0.0271(14) 0.0361(16) 0.0244(14) 0.0024(11) 0.0046(11) -0.0020(12) C25 0.0313(15) 0.0345(16) 0.0238(14) -0.0028(11) 0.0058(12) -0.0069(12) C26 0.0314(15) 0.0309(15) 0.0296(15) -0.0036(12) 0.0058(12) -0.0034(12) C27 0.0253(14) 0.0308(15) 0.0248(14) -0.0016(11) 0.0052(11) -0.0015(11) C29 0.0234(13) 0.0255(14) 0.0250(14) 0.0002(10) 0.0041(11) -0.0007(11) C30 0.0400(17) 0.0412(18) 0.0274(15) -0.0073(13) 0.0022(13) -0.0074(14) C31 0.0287(14) 0.0284(14) 0.0222(13) 0.0026(11) 0.0040(11) 0.0006(11) C32 0.0251(14) 0.0325(16) 0.0402(17) -0.0007(13) 0.0015(13) 0.0021(12) C33 0.0278(15) 0.0325(16) 0.0451(18) -0.0008(13) 0.0003(13) -0.0025(12) C34 0.0321(15) 0.0309(15) 0.0285(15) 0.0019(12) 0.0074(12) 0.0014(12) C35 0.0275(15) 0.0377(17) 0.0317(16) 0.0038(12) 0.0039(12) 0.0046(12) C36 0.0260(14) 0.0336(16) 0.0330(15) 0.0004(12) 0.0026(12) -0.0040(12) C37 0.0390(18) 0.0380(18) 0.0442(19) 0.0073(14) 0.0070(15) 0.0083(14) C41 0.0338(15) 0.0260(14) 0.0322(15) 0.0012(12) 0.0095(13) -0.0031(12) C42 0.0354(16) 0.0260(15) 0.0353(16) 0.0012(12) 0.0092(13) 0.0042(12) C43 0.0395(17) 0.0266(15) 0.0352(17) -0.0040(13) 0.0002(13) 0.0033(13) Cl1 0.0414(5) 0.0737(7) 0.0691(7) 0.0187(5) -0.0011(5) -0.0055(5) Cl2 0.0525(6) 0.0750(8) 0.0689(7) -0.0125(5) 0.0156(5) 0.0025(5) C44 0.059(2) 0.048(2) 0.056(2) 0.0026(18) 0.0067(19) 0.0103(18) _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 O14 C14 1.379(3) . ? O14 C17 1.420(4) . ? O34 C34 1.375(4) . ? O34 C37 1.422(4) . ? N1 C9 1.322(4) . ? N1 C2 1.387(3) . ? N8 C9 1.380(4) . ? N8 C7 1.381(4) . ? N8 C41 1.463(3) . ? N21 C29 1.320(4) . ? N21 C22 1.388(3) . ? N28 C27 1.374(4) . ? N28 C29 1.394(4) . ? N28 C43 1.469(4) . ? C2 C7 1.406(4) . ? C2 C3 1.410(4) . ? C3 C4 1.392(4) . ? C3 C11 1.485(4) . ? C4 C5 1.404(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 C10 1.513(4) . ? C6 C7 1.397(4) . ? C6 H6 0.9500 . ? C9 C29 1.457(4) . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 C12 1.396(4) . ? C11 C16 1.397(4) . ? C12 C13 1.390(4) . ? C12 H12 0.9500 . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C14 C15 1.389(4) . ? C15 C16 1.371(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C22 C27 1.413(4) . ? C22 C23 1.413(4) . ? C23 C24 1.390(4) . ? C23 C31 1.487(4) . ? C24 C25 1.404(4) . ? C24 H24 0.9500 . ? C25 C26 1.387(4) . ? C25 C30 1.510(4) . ? C26 C27 1.390(4) . ? C26 H26 0.9500 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 C36 1.389(4) . ? C31 C32 1.396(4) . ? C32 C33 1.385(4) . ? C32 H32 0.9500 . ? C33 C34 1.384(4) . ? C33 H33 0.9500 . ? C34 C35 1.384(4) . ? C35 C36 1.393(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H371 0.9800 . ? C37 H372 0.9800 . ? C37 H373 0.9800 . ? C41 C42 1.517(4) . ? C41 H411 0.9900 . ? C41 H412 0.9900 . ? C42 C43 1.501(4) . ? C42 H421 0.9900 . ? C42 H422 0.9900 . ? C43 H431 0.9900 . ? C43 H432 0.9900 . ? Cl1 C44 1.754(4) . ? Cl2 C44 1.753(4) . ? C44 H441 0.9900 . ? C44 H442 0.9900 . ? 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 C14 O14 C17 117.2(2) . . ? C34 O34 C37 117.5(2) . . ? C9 N1 C2 104.8(2) . . ? C9 N8 C7 106.5(2) . . ? C9 N8 C41 127.8(2) . . ? C7 N8 C41 125.4(2) . . ? C29 N21 C22 105.7(2) . . ? C27 N28 C29 106.2(2) . . ? C27 N28 C43 120.0(2) . . ? C29 N28 C43 133.7(2) . . ? N1 C2 C7 110.3(2) . . ? N1 C2 C3 130.3(3) . . ? C7 C2 C3 119.5(2) . . ? C4 C3 C2 116.2(3) . . ? C4 C3 C11 119.3(2) . . ? C2 C3 C11 124.5(2) . . ? C3 C4 C5 124.1(3) . . ? C3 C4 H4 117.9 . . ? C5 C4 H4 117.9 . . ? C6 C5 C4 119.4(3) . . ? C6 C5 C10 121.2(3) . . ? C4 C5 C10 119.4(3) . . ? C5 C6 C7 117.5(3) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? N8 C7 C6 131.4(3) . . ? N8 C7 C2 105.4(2) . . ? C6 C7 C2 123.2(3) . . ? N1 C9 N8 113.0(2) . . ? N1 C9 C29 122.2(2) . . ? N8 C9 C29 124.8(2) . . ? C5 C10 H101 109.5 . . ? C5 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C5 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C12 C11 C16 117.7(3) . . ? C12 C11 C3 122.3(2) . . ? C16 C11 C3 119.9(3) . . ? C13 C12 C11 121.6(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 118.9(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? O14 C14 C13 124.2(3) . . ? O14 C14 C15 115.4(3) . . ? C13 C14 C15 120.4(3) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.4(3) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? O14 C17 H171 109.5 . . ? O14 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? O14 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? N21 C22 C27 109.3(2) . . ? N21 C22 C23 131.3(3) . . ? C27 C22 C23 119.3(2) . . ? C24 C23 C22 116.1(3) . . ? C24 C23 C31 120.1(3) . . ? C22 C23 C31 123.8(2) . . ? C23 C24 C25 124.3(3) . . ? C23 C24 H24 117.8 . . ? C25 C24 H24 117.8 . . ? C26 C25 C24 119.5(3) . . ? C26 C25 C30 120.5(3) . . ? C24 C25 C30 120.0(3) . . ? C25 C26 C27 117.3(3) . . ? C25 C26 H26 121.3 . . ? C27 C26 H26 121.3 . . ? N28 C27 C26 130.3(3) . . ? N28 C27 C22 106.2(2) . . ? C26 C27 C22 123.4(3) . . ? N21 C29 N28 112.5(2) . . ? N21 C29 C9 121.5(2) . . ? N28 C29 C9 126.0(2) . . ? C25 C30 H301 109.5 . . ? C25 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C25 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C36 C31 C32 117.1(3) . . ? C36 C31 C23 120.3(3) . . ? C32 C31 C23 122.5(3) . . ? C33 C32 C31 121.1(3) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C34 C33 C32 120.7(3) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? O34 C34 C33 116.1(3) . . ? O34 C34 C35 124.4(3) . . ? C33 C34 C35 119.5(3) . . ? C34 C35 C36 119.3(3) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C31 C36 C35 122.3(3) . . ? C31 C36 H36 118.9 . . ? C35 C36 H36 118.9 . . ? O34 C37 H371 109.5 . . ? O34 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? O34 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? N8 C41 C42 110.8(2) . . ? N8 C41 H411 109.5 . . ? C42 C41 H411 109.5 . . ? N8 C41 H412 109.5 . . ? C42 C41 H412 109.5 . . ? H411 C41 H412 108.1 . . ? C43 C42 C41 113.6(3) . . ? C43 C42 H421 108.9 . . ? C41 C42 H421 108.9 . . ? C43 C42 H422 108.9 . . ? C41 C42 H422 108.9 . . ? H421 C42 H422 107.7 . . ? N28 C43 C42 116.1(2) . . ? N28 C43 H431 108.3 . . ? C42 C43 H431 108.3 . . ? N28 C43 H432 108.3 . . ? C42 C43 H432 108.3 . . ? H431 C43 H432 107.4 . . ? Cl2 C44 Cl1 111.9(2) . . ? Cl2 C44 H441 109.2 . . ? Cl1 C44 H441 109.2 . . ? Cl2 C44 H442 109.2 . . ? Cl1 C44 H442 109.2 . . ? H441 C44 H442 107.9 . . ? 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 C9 N1 C2 C7 -0.8(3) . . . . ? C9 N1 C2 C3 179.3(3) . . . . ? N1 C2 C3 C4 -179.5(3) . . . . ? C7 C2 C3 C4 0.6(4) . . . . ? N1 C2 C3 C11 0.4(5) . . . . ? C7 C2 C3 C11 -179.5(2) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C11 C3 C4 C5 179.8(3) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C3 C4 C5 C10 179.4(3) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C10 C5 C6 C7 -179.3(3) . . . . ? C9 N8 C7 C6 -179.1(3) . . . . ? C41 N8 C7 C6 -4.7(5) . . . . ? C9 N8 C7 C2 -0.3(3) . . . . ? C41 N8 C7 C2 174.0(2) . . . . ? C5 C6 C7 N8 178.6(3) . . . . ? C5 C6 C7 C2 0.1(4) . . . . ? N1 C2 C7 N8 0.7(3) . . . . ? C3 C2 C7 N8 -179.4(2) . . . . ? N1 C2 C7 C6 179.6(2) . . . . ? C3 C2 C7 C6 -0.5(4) . . . . ? C2 N1 C9 N8 0.6(3) . . . . ? C2 N1 C9 C29 179.6(2) . . . . ? C7 N8 C9 N1 -0.2(3) . . . . ? C41 N8 C9 N1 -174.4(2) . . . . ? C7 N8 C9 C29 -179.1(3) . . . . ? C41 N8 C9 C29 6.7(4) . . . . ? C4 C3 C11 C12 134.2(3) . . . . ? C2 C3 C11 C12 -45.7(4) . . . . ? C4 C3 C11 C16 -43.5(4) . . . . ? C2 C3 C11 C16 136.6(3) . . . . ? C16 C11 C12 C13 2.2(4) . . . . ? C3 C11 C12 C13 -175.5(3) . . . . ? C11 C12 C13 C14 -1.6(5) . . . . ? C17 O14 C14 C13 4.2(5) . . . . ? C17 O14 C14 C15 -175.1(3) . . . . ? C12 C13 C14 O14 -179.4(3) . . . . ? C12 C13 C14 C15 -0.1(5) . . . . ? O14 C14 C15 C16 -179.6(3) . . . . ? C13 C14 C15 C16 1.1(5) . . . . ? C14 C15 C16 C11 -0.4(5) . . . . ? C12 C11 C16 C15 -1.3(4) . . . . ? C3 C11 C16 C15 176.5(3) . . . . ? C29 N21 C22 C27 -0.7(3) . . . . ? C29 N21 C22 C23 177.8(3) . . . . ? N21 C22 C23 C24 -179.0(3) . . . . ? C27 C22 C23 C24 -0.7(4) . . . . ? N21 C22 C23 C31 -0.1(5) . . . . ? C27 C22 C23 C31 178.2(2) . . . . ? C22 C23 C24 C25 -0.3(4) . . . . ? C31 C23 C24 C25 -179.2(3) . . . . ? C23 C24 C25 C26 1.1(4) . . . . ? C23 C24 C25 C30 -179.3(3) . . . . ? C24 C25 C26 C27 -0.9(4) . . . . ? C30 C25 C26 C27 179.5(3) . . . . ? C29 N28 C27 C26 -179.0(3) . . . . ? C43 N28 C27 C26 0.4(5) . . . . ? C29 N28 C27 C22 0.0(3) . . . . ? C43 N28 C27 C22 179.3(2) . . . . ? C25 C26 C27 N28 178.8(3) . . . . ? C25 C26 C27 C22 0.0(4) . . . . ? N21 C22 C27 N28 0.4(3) . . . . ? C23 C22 C27 N28 -178.2(2) . . . . ? N21 C22 C27 C26 179.5(3) . . . . ? C23 C22 C27 C26 0.8(4) . . . . ? C22 N21 C29 N28 0.7(3) . . . . ? C22 N21 C29 C9 -179.9(2) . . . . ? C27 N28 C29 N21 -0.5(3) . . . . ? C43 N28 C29 N21 -179.7(3) . . . . ? C27 N28 C29 C9 -179.9(3) . . . . ? C43 N28 C29 C9 0.9(5) . . . . ? N1 C9 C29 N21 -21.2(4) . . . . ? N8 C9 C29 N21 157.6(3) . . . . ? N1 C9 C29 N28 158.1(3) . . . . ? N8 C9 C29 N28 -23.1(4) . . . . ? C24 C23 C31 C36 34.2(4) . . . . ? C22 C23 C31 C36 -144.7(3) . . . . ? C24 C23 C31 C32 -142.8(3) . . . . ? C22 C23 C31 C32 38.3(4) . . . . ? C36 C31 C32 C33 -2.0(4) . . . . ? C23 C31 C32 C33 175.2(3) . . . . ? C31 C32 C33 C34 0.3(5) . . . . ? C37 O34 C34 C33 177.8(3) . . . . ? C37 O34 C34 C35 -2.8(4) . . . . ? C32 C33 C34 O34 -179.2(3) . . . . ? C32 C33 C34 C35 1.5(5) . . . . ? O34 C34 C35 C36 179.3(3) . . . . ? C33 C34 C35 C36 -1.4(4) . . . . ? C32 C31 C36 C35 2.0(4) . . . . ? C23 C31 C36 C35 -175.2(3) . . . . ? C34 C35 C36 C31 -0.4(4) . . . . ? C9 N8 C41 C42 49.2(4) . . . . ? C7 N8 C41 C42 -124.0(3) . . . . ? N8 C41 C42 C43 -84.9(3) . . . . ? C27 N28 C43 C42 172.4(3) . . . . ? C29 N28 C43 C42 -8.5(5) . . . . ? C41 C42 C43 N28 56.6(4) . . . . ? # End of CIF ============================================================ # Attachment '3d.cif' data_SG0626 _database_code_depnum_ccdc_archive 'CCDC 710117' _audit_creation_method SHELXL-97 _audit_creation_date 06-08-04 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C37 H38 N4 O2, 2(C H2 Cl2)' _chemical_formula_sum 'C39 H42 Cl4 N4 O2' _chemical_formula_weight 740.60 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 312 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 336 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 32 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 32 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 16 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 20.2497(2) _cell_length_b 14.7082(2) _cell_length_c 24.9430(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7428.94(17) _cell_formula_units_Z 8 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 104889 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3104 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_absorpt_correction_T_min 0.751 _exptl_absorpt_correction_T_max 0.943 _exptl_special_details ; Solvent used: dichloromethane / hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.587(1) Frames collected: 411 Seconds exposure per frame: 33 Degrees rotation per frame: 1.1 Crystal-Detector distance (mm): 37.4 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 89418 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 8506 _reflns_number_gt 6208 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+5.2510P] 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 0.0141(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8506 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.401 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.075 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 O14 O 0.24517(8) 0.41133(12) 0.67092(6) 0.0424(4) Uani 1 1 d . . . O34 O -0.03332(9) 0.25469(11) 0.87350(6) 0.0397(4) Uani 1 1 d . . . N1 N 0.03689(8) 0.18243(11) 0.54024(6) 0.0228(4) Uani 1 1 d . . . N8 N -0.00821(8) 0.10205(11) 0.47244(6) 0.0219(3) Uani 1 1 d . . . N21 N -0.06969(8) 0.14765(11) 0.60905(6) 0.0233(4) Uani 1 1 d . . . N28 N -0.13755(8) 0.10746(11) 0.54137(6) 0.0222(4) Uani 1 1 d . . . C2 C 0.08246(10) 0.17354(13) 0.49913(8) 0.0237(4) Uani 1 1 d . . . C3 C 0.14720(10) 0.20948(14) 0.49524(8) 0.0245(4) Uani 1 1 d . . . C4 C 0.18054(10) 0.19104(15) 0.44834(8) 0.0284(5) Uani 1 1 d . . . H4 H 0.2242 0.2139 0.4445 0.034 Uiso 1 1 calc R . . C5 C 0.15342(11) 0.13993(14) 0.40551(8) 0.0284(5) Uani 1 1 d . . . C6 C 0.09027(10) 0.10496(14) 0.40974(8) 0.0270(4) Uani 1 1 d . . . H6 H 0.0713 0.0698 0.3817 0.032 Uiso 1 1 calc R . . C7 C 0.05558(10) 0.12333(13) 0.45673(8) 0.0233(4) Uani 1 1 d . . . C9 C -0.01608(9) 0.13863(13) 0.52272(7) 0.0218(4) Uani 1 1 d . . . C10 C 0.19374(12) 0.12506(17) 0.35568(9) 0.0382(5) Uani 1 1 d . . . H101 H 0.1755 0.0737 0.3355 0.057 Uiso 1 1 calc R . . H102 H 0.2396 0.1118 0.3656 0.057 Uiso 1 1 calc R . . H103 H 0.1924 0.1799 0.3334 0.057 Uiso 1 1 calc R . . C11 C 0.17527(10) 0.26564(14) 0.53957(8) 0.0251(4) Uani 1 1 d . . . C12 C 0.14978(10) 0.35286(14) 0.54937(8) 0.0270(4) Uani 1 1 d . . . C13 C 0.17258(10) 0.40316(15) 0.59333(8) 0.0296(5) Uani 1 1 d . . . H13 H 0.1551 0.4620 0.6002 0.036 Uiso 1 1 calc R . . C14 C 0.22044(11) 0.36737(16) 0.62682(8) 0.0306(5) Uani 1 1 d . . . C15 C 0.24732(10) 0.28284(16) 0.61604(8) 0.0302(5) Uani 1 1 d . . . H15 H 0.2810 0.2595 0.6387 0.036 Uiso 1 1 calc R . . C16 C 0.22573(10) 0.23143(15) 0.57254(8) 0.0285(5) Uani 1 1 d . . . C17 C 0.09911(12) 0.39503(16) 0.51261(9) 0.0342(5) Uani 1 1 d . . . H171 H 0.0562 0.3660 0.5185 0.051 Uiso 1 1 calc R . . H172 H 0.1127 0.3863 0.4752 0.051 Uiso 1 1 calc R . . H173 H 0.0956 0.4602 0.5202 0.051 Uiso 1 1 calc R . . C18 C 0.20764(14) 0.48390(18) 0.69243(10) 0.0453(6) Uani 1 1 d . . . H181 H 0.2115 0.5371 0.6690 0.068 Uiso 1 1 calc R . . H182 H 0.2243 0.4991 0.7282 0.068 Uiso 1 1 calc R . . H183 H 0.1612 0.4657 0.6950 0.068 Uiso 1 1 calc R . . C19 C 0.25604(12) 0.13921(16) 0.56313(10) 0.0387(5) Uani 1 1 d . . . H191 H 0.2966 0.1336 0.5843 0.058 Uiso 1 1 calc R . . H192 H 0.2665 0.1322 0.5250 0.058 Uiso 1 1 calc R . . H193 H 0.2247 0.0918 0.5740 0.058 Uiso 1 1 calc R . . C22 C -0.13331(10) 0.13890(13) 0.62841(8) 0.0229(4) Uani 1 1 d . . . C23 C -0.15810(10) 0.15446(14) 0.68039(8) 0.0253(4) Uani 1 1 d . . . C24 C -0.22537(10) 0.14191(15) 0.68696(8) 0.0279(4) Uani 1 1 d . . . H24 H -0.2437 0.1528 0.7214 0.034 Uiso 1 1 calc R . . C25 C -0.26832(10) 0.11395(15) 0.64566(8) 0.0281(4) Uani 1 1 d . . . C26 C -0.24363(10) 0.09848(14) 0.59455(8) 0.0269(4) Uani 1 1 d . . . H26 H -0.2714 0.0791 0.5661 0.032 Uiso 1 1 calc R . . C27 C -0.17612(10) 0.11281(13) 0.58701(8) 0.0239(4) Uani 1 1 d . . . C29 C -0.07428(9) 0.12906(13) 0.55721(7) 0.0214(4) Uani 1 1 d . . . C30 C -0.34072(11) 0.10258(18) 0.65707(10) 0.0387(6) Uani 1 1 d . . . H301 H -0.3622 0.1623 0.6571 0.058 Uiso 1 1 calc R . . H302 H -0.3465 0.0739 0.6922 0.058 Uiso 1 1 calc R . . H303 H -0.3607 0.0641 0.6294 0.058 Uiso 1 1 calc R . . C31 C -0.11674(10) 0.18351(15) 0.72712(8) 0.0253(4) Uani 1 1 d . . . C32 C -0.07313(10) 0.12256(14) 0.75157(8) 0.0264(4) Uani 1 1 d . . . C33 C -0.04365(11) 0.14573(15) 0.80035(8) 0.0297(5) Uani 1 1 d . . . H33 H -0.0144 0.1042 0.8173 0.036 Uiso 1 1 calc R . . C34 C -0.05681(11) 0.22888(15) 0.82412(8) 0.0288(5) Uani 1 1 d . . . C35 C -0.09544(11) 0.29217(15) 0.79762(8) 0.0307(5) Uani 1 1 d . . . H35 H -0.1012 0.3511 0.8125 0.037 Uiso 1 1 calc R . . C36 C -0.12577(10) 0.27047(15) 0.74964(8) 0.0282(4) Uani 1 1 d . . . C37 C -0.05760(12) 0.03110(15) 0.72688(9) 0.0341(5) Uani 1 1 d . . . H371 H -0.0302 0.0398 0.6949 0.051 Uiso 1 1 calc R . . H372 H -0.0988 0.0007 0.7168 0.051 Uiso 1 1 calc R . . H373 H -0.0337 -0.0064 0.7529 0.051 Uiso 1 1 calc R . . C38 C -0.01205(13) 0.18446(17) 0.90822(9) 0.0407(6) Uani 1 1 d . . . H381 H -0.0449 0.1355 0.9085 0.061 Uiso 1 1 calc R . . H382 H -0.0069 0.2087 0.9446 0.061 Uiso 1 1 calc R . . H383 H 0.0304 0.1605 0.8957 0.061 Uiso 1 1 calc R . . C39 C -0.16895(13) 0.34142(17) 0.72323(9) 0.0381(5) Uani 1 1 d . . . H391 H -0.2146 0.3340 0.7355 0.057 Uiso 1 1 calc R . . H392 H -0.1671 0.3340 0.6842 0.057 Uiso 1 1 calc R . . H393 H -0.1531 0.4022 0.7329 0.057 Uiso 1 1 calc R . . C41 C -0.05689(10) 0.05720(14) 0.43783(8) 0.0251(4) Uani 1 1 d . . . H411 H -0.0604 -0.0076 0.4482 0.030 Uiso 1 1 calc R . . H412 H -0.0413 0.0596 0.4002 0.030 Uiso 1 1 calc R . . C42 C -0.12444(10) 0.10079(15) 0.44132(8) 0.0262(4) Uani 1 1 d . . . H421 H -0.1499 0.0842 0.4089 0.031 Uiso 1 1 calc R . . H422 H -0.1190 0.1677 0.4412 0.031 Uiso 1 1 calc R . . C43 C -0.16404(10) 0.07396(15) 0.49041(8) 0.0273(4) Uani 1 1 d . . . H431 H -0.2097 0.0971 0.4862 0.033 Uiso 1 1 calc R . . H432 H -0.1664 0.0068 0.4920 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.12548(4) 0.08791(6) 0.67566(3) 0.0643(2) Uani 1 1 d . . . Cl2 Cl 0.09311(6) 0.26257(6) 0.72346(3) 0.0803(3) Uani 1 1 d . . . C51 C 0.08530(13) 0.1936(2) 0.66686(10) 0.0469(6) Uani 1 1 d . . . H511 H 0.1045 0.2252 0.6355 0.056 Uiso 1 1 calc R . . H512 H 0.0379 0.1829 0.6595 0.056 Uiso 1 1 calc R . . Cl3 Cl -0.00715(4) 0.44884(5) 0.62760(4) 0.0702(3) Uani 1 1 d . . . Cl4 Cl -0.10943(5) 0.36249(6) 0.56336(4) 0.0701(3) Uani 1 1 d . . . C52 C -0.04446(13) 0.34557(17) 0.60928(11) 0.0434(6) Uani 1 1 d . . . H521 H -0.0618 0.3152 0.6418 0.052 Uiso 1 1 calc R . . H522 H -0.0109 0.3052 0.5930 0.052 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 O14 0.0422(9) 0.0497(10) 0.0355(8) -0.0167(8) -0.0094(7) -0.0011(8) O34 0.0589(11) 0.0306(8) 0.0296(8) -0.0056(7) -0.0195(8) 0.0067(8) N1 0.0239(8) 0.0232(9) 0.0214(8) 0.0001(6) -0.0004(7) -0.0012(7) N8 0.0236(8) 0.0230(8) 0.0191(8) -0.0017(6) -0.0008(6) -0.0014(7) N21 0.0248(8) 0.0243(9) 0.0206(8) -0.0002(7) -0.0009(7) -0.0009(7) N28 0.0222(8) 0.0246(9) 0.0198(8) -0.0007(6) -0.0008(6) -0.0014(7) C2 0.0271(10) 0.0223(10) 0.0216(9) 0.0004(8) 0.0002(8) 0.0007(8) C3 0.0255(10) 0.0226(10) 0.0255(10) 0.0007(8) -0.0009(8) -0.0020(8) C4 0.0258(10) 0.0290(11) 0.0306(11) -0.0009(9) 0.0042(9) -0.0037(8) C5 0.0308(11) 0.0282(11) 0.0262(10) -0.0016(8) 0.0054(9) -0.0012(9) C6 0.0310(11) 0.0265(11) 0.0235(10) -0.0034(8) -0.0002(8) -0.0005(9) C7 0.0253(10) 0.0214(10) 0.0231(9) 0.0009(8) -0.0016(8) -0.0009(8) C9 0.0239(10) 0.0223(10) 0.0193(9) 0.0004(7) -0.0027(7) 0.0004(8) C10 0.0398(13) 0.0430(14) 0.0319(12) -0.0073(10) 0.0113(10) -0.0081(11) C11 0.0240(10) 0.0274(10) 0.0240(10) 0.0004(8) 0.0023(8) -0.0056(8) C12 0.0268(10) 0.0278(11) 0.0263(10) 0.0002(8) 0.0021(8) -0.0058(8) C13 0.0293(11) 0.0284(11) 0.0312(11) -0.0045(9) 0.0008(9) -0.0036(9) C14 0.0279(11) 0.0379(12) 0.0261(10) -0.0039(9) -0.0004(9) -0.0098(9) C15 0.0250(10) 0.0368(12) 0.0289(10) 0.0002(9) -0.0027(9) -0.0038(9) C16 0.0255(10) 0.0300(11) 0.0299(11) 0.0002(9) 0.0020(8) -0.0038(9) C17 0.0377(12) 0.0310(12) 0.0339(12) -0.0022(9) -0.0065(10) 0.0010(10) C18 0.0574(16) 0.0448(15) 0.0338(12) -0.0135(11) -0.0013(11) -0.0041(12) C19 0.0371(13) 0.0364(13) 0.0425(13) -0.0038(10) -0.0080(11) 0.0063(10) C22 0.0229(9) 0.0237(10) 0.0220(9) 0.0012(8) -0.0010(8) -0.0005(8) C23 0.0262(10) 0.0278(10) 0.0219(10) 0.0004(8) -0.0013(8) 0.0008(8) C24 0.0310(11) 0.0310(11) 0.0218(10) 0.0009(8) 0.0027(8) 0.0010(9) C25 0.0267(10) 0.0288(11) 0.0288(11) 0.0021(9) 0.0004(9) -0.0005(8) C26 0.0260(10) 0.0281(11) 0.0264(10) -0.0007(8) -0.0030(8) -0.0017(8) C27 0.0261(10) 0.0238(10) 0.0217(9) -0.0003(8) -0.0013(8) 0.0005(8) C29 0.0224(9) 0.0203(9) 0.0215(9) 0.0000(7) -0.0027(7) -0.0017(8) C30 0.0278(11) 0.0540(15) 0.0341(12) -0.0031(11) 0.0033(10) -0.0056(11) C31 0.0251(10) 0.0322(11) 0.0186(9) -0.0008(8) 0.0009(8) -0.0018(8) C32 0.0291(10) 0.0278(11) 0.0224(9) -0.0011(8) 0.0026(8) -0.0013(8) C33 0.0352(11) 0.0276(11) 0.0263(10) 0.0007(8) -0.0069(9) 0.0037(9) C34 0.0337(11) 0.0311(11) 0.0215(9) -0.0031(8) -0.0053(9) -0.0005(9) C35 0.0377(12) 0.0278(11) 0.0266(10) -0.0039(9) -0.0027(9) 0.0040(9) C36 0.0296(10) 0.0317(11) 0.0233(10) 0.0016(8) -0.0011(8) 0.0030(9) C37 0.0420(12) 0.0306(12) 0.0298(11) -0.0036(9) -0.0040(10) 0.0046(10) C38 0.0559(15) 0.0366(13) 0.0298(11) -0.0048(10) -0.0160(11) 0.0083(11) C39 0.0462(14) 0.0372(13) 0.0309(11) -0.0031(10) -0.0098(10) 0.0110(11) C41 0.0282(10) 0.0247(10) 0.0222(9) -0.0022(8) -0.0046(8) -0.0011(8) C42 0.0276(10) 0.0308(11) 0.0202(9) -0.0012(8) -0.0047(8) 0.0007(9) C43 0.0243(10) 0.0360(11) 0.0217(10) -0.0047(8) -0.0039(8) -0.0039(9) Cl1 0.0605(5) 0.0619(5) 0.0704(5) -0.0011(4) -0.0058(4) 0.0075(4) Cl2 0.1307(8) 0.0643(5) 0.0459(4) -0.0073(4) 0.0081(5) -0.0078(5) C51 0.0438(14) 0.0566(17) 0.0403(14) 0.0026(12) -0.0041(11) -0.0046(12) Cl3 0.0656(5) 0.0378(4) 0.1074(7) -0.0276(4) 0.0137(4) -0.0087(3) Cl4 0.0783(6) 0.0546(5) 0.0775(6) 0.0076(4) -0.0200(4) 0.0052(4) C52 0.0485(15) 0.0288(12) 0.0530(15) -0.0069(11) 0.0047(12) -0.0030(11) _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 O14 C14 1.371(3) . ? O14 C18 1.416(3) . ? O34 C34 1.374(2) . ? O34 C38 1.415(3) . ? N1 C9 1.325(3) . ? N1 C2 1.386(3) . ? N8 C9 1.374(2) . ? N8 C7 1.386(3) . ? N8 C41 1.467(2) . ? N21 C29 1.325(2) . ? N21 C22 1.382(3) . ? N28 C29 1.378(2) . ? N28 C27 1.383(3) . ? N28 C43 1.465(2) . ? C2 C7 1.400(3) . ? C2 C3 1.417(3) . ? C3 C4 1.378(3) . ? C3 C11 1.493(3) . ? C4 C5 1.417(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 C10 1.503(3) . ? C6 C7 1.393(3) . ? C6 H6 0.9500 . ? C9 C29 1.466(3) . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 C12 1.404(3) . ? C11 C16 1.405(3) . ? C12 C13 1.401(3) . ? C12 C17 1.509(3) . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C15 C16 1.393(3) . ? C15 H15 0.9500 . ? C16 C19 1.507(3) . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C22 C27 1.402(3) . ? C22 C23 1.409(3) . ? C23 C24 1.384(3) . ? C23 C31 1.498(3) . ? C24 C25 1.410(3) . ? C24 H24 0.9500 . ? C25 C26 1.388(3) . ? C25 C30 1.503(3) . ? C26 C27 1.396(3) . ? C26 H26 0.9500 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 C32 1.398(3) . ? C31 C36 1.409(3) . ? C32 C33 1.397(3) . ? C32 C37 1.513(3) . ? C33 C34 1.385(3) . ? C33 H33 0.9500 . ? C34 C35 1.384(3) . ? C35 C36 1.383(3) . ? C35 H35 0.9500 . ? C36 C39 1.512(3) . ? C37 H371 0.9800 . ? C37 H372 0.9800 . ? C37 H373 0.9800 . ? C38 H381 0.9800 . ? C38 H382 0.9800 . ? C38 H383 0.9800 . ? C39 H391 0.9800 . ? C39 H392 0.9800 . ? C39 H393 0.9800 . ? C41 C42 1.513(3) . ? C41 H411 0.9900 . ? C41 H412 0.9900 . ? C42 C43 1.516(3) . ? C42 H421 0.9900 . ? C42 H422 0.9900 . ? C43 H431 0.9900 . ? C43 H432 0.9900 . ? Cl1 C51 1.768(3) . ? Cl2 C51 1.746(3) . ? C51 H511 0.9900 . ? C51 H512 0.9900 . ? Cl3 C52 1.757(3) . ? Cl4 C52 1.762(3) . ? C52 H521 0.9900 . ? C52 H522 0.9900 . ? 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 C14 O14 C18 117.63(19) . . ? C34 O34 C38 116.89(17) . . ? C9 N1 C2 104.43(16) . . ? C9 N8 C7 106.12(16) . . ? C9 N8 C41 129.44(16) . . ? C7 N8 C41 124.17(16) . . ? C29 N21 C22 104.86(16) . . ? C29 N28 C27 106.03(15) . . ? C29 N28 C43 131.82(16) . . ? C27 N28 C43 121.77(16) . . ? N1 C2 C7 110.47(17) . . ? N1 C2 C3 129.18(18) . . ? C7 C2 C3 120.32(18) . . ? C4 C3 C2 115.99(18) . . ? C4 C3 C11 123.46(18) . . ? C2 C3 C11 120.54(17) . . ? C3 C4 C5 123.69(19) . . ? C3 C4 H4 118.2 . . ? C5 C4 H4 118.2 . . ? C6 C5 C4 119.88(18) . . ? C6 C5 C10 120.77(19) . . ? C4 C5 C10 119.35(19) . . ? C5 C6 C7 117.31(19) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? N8 C7 C6 131.63(18) . . ? N8 C7 C2 105.54(16) . . ? C6 C7 C2 122.80(18) . . ? N1 C9 N8 113.42(17) . . ? N1 C9 C29 120.26(17) . . ? N8 C9 C29 126.25(17) . . ? C5 C10 H101 109.5 . . ? C5 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C5 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C12 C11 C16 119.52(19) . . ? C12 C11 C3 119.64(18) . . ? C16 C11 C3 120.82(19) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 C17 118.85(19) . . ? C11 C12 C17 121.30(18) . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? O14 C14 C15 115.9(2) . . ? O14 C14 C13 124.1(2) . . ? C15 C14 C13 120.01(19) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 119.3(2) . . ? C15 C16 C19 118.8(2) . . ? C11 C16 C19 121.83(19) . . ? C12 C17 H171 109.5 . . ? C12 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C12 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? O14 C18 H181 109.5 . . ? O14 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? O14 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C16 C19 H191 109.5 . . ? C16 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C16 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? N21 C22 C27 110.17(17) . . ? N21 C22 C23 129.68(18) . . ? C27 C22 C23 120.12(18) . . ? C24 C23 C22 115.96(18) . . ? C24 C23 C31 119.76(18) . . ? C22 C23 C31 124.28(18) . . ? C23 C24 C25 124.02(19) . . ? C23 C24 H24 118.0 . . ? C25 C24 H24 118.0 . . ? C26 C25 C24 119.78(19) . . ? C26 C25 C30 120.48(19) . . ? C24 C25 C30 119.73(19) . . ? C25 C26 C27 116.86(18) . . ? C25 C26 H26 121.6 . . ? C27 C26 H26 121.6 . . ? N28 C27 C26 130.96(18) . . ? N28 C27 C22 105.82(17) . . ? C26 C27 C22 123.21(18) . . ? N21 C29 N28 113.12(17) . . ? N21 C29 C9 119.77(17) . . ? N28 C29 C9 126.97(17) . . ? C25 C30 H301 109.5 . . ? C25 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C25 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C32 C31 C36 119.35(18) . . ? C32 C31 C23 120.64(19) . . ? C36 C31 C23 119.78(18) . . ? C33 C32 C31 119.55(19) . . ? C33 C32 C37 118.86(19) . . ? C31 C32 C37 121.59(18) . . ? C34 C33 C32 120.39(19) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? O34 C34 C35 115.98(19) . . ? O34 C34 C33 124.14(19) . . ? C35 C34 C33 119.88(19) . . ? C36 C35 C34 120.6(2) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 119.80(19) . . ? C35 C36 C39 118.3(2) . . ? C31 C36 C39 121.86(19) . . ? C32 C37 H371 109.5 . . ? C32 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? C32 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? O34 C38 H381 109.5 . . ? O34 C38 H382 109.5 . . ? H381 C38 H382 109.5 . . ? O34 C38 H383 109.5 . . ? H381 C38 H383 109.5 . . ? H382 C38 H383 109.5 . . ? C36 C39 H391 109.5 . . ? C36 C39 H392 109.5 . . ? H391 C39 H392 109.5 . . ? C36 C39 H393 109.5 . . ? H391 C39 H393 109.5 . . ? H392 C39 H393 109.5 . . ? N8 C41 C42 112.52(16) . . ? N8 C41 H411 109.1 . . ? C42 C41 H411 109.1 . . ? N8 C41 H412 109.1 . . ? C42 C41 H412 109.1 . . ? H411 C41 H412 107.8 . . ? C41 C42 C43 114.48(17) . . ? C41 C42 H421 108.6 . . ? C43 C42 H421 108.6 . . ? C41 C42 H422 108.6 . . ? C43 C42 H422 108.6 . . ? H421 C42 H422 107.6 . . ? N28 C43 C42 114.80(16) . . ? N28 C43 H431 108.6 . . ? C42 C43 H431 108.6 . . ? N28 C43 H432 108.6 . . ? C42 C43 H432 108.6 . . ? H431 C43 H432 107.5 . . ? Cl2 C51 Cl1 111.65(15) . . ? Cl2 C51 H511 109.3 . . ? Cl1 C51 H511 109.3 . . ? Cl2 C51 H512 109.3 . . ? Cl1 C51 H512 109.3 . . ? H511 C51 H512 108.0 . . ? Cl3 C52 Cl4 111.60(15) . . ? Cl3 C52 H521 109.3 . . ? Cl4 C52 H521 109.3 . . ? Cl3 C52 H522 109.3 . . ? Cl4 C52 H522 109.3 . . ? H521 C52 H522 108.0 . . ? 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 C9 N1 C2 C7 -0.1(2) . . . . ? C9 N1 C2 C3 177.8(2) . . . . ? N1 C2 C3 C4 -178.3(2) . . . . ? C7 C2 C3 C4 -0.5(3) . . . . ? N1 C2 C3 C11 0.2(3) . . . . ? C7 C2 C3 C11 177.97(18) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C11 C3 C4 C5 -178.1(2) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C3 C4 C5 C10 179.0(2) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? C10 C5 C6 C7 -178.7(2) . . . . ? C9 N8 C7 C6 -179.1(2) . . . . ? C41 N8 C7 C6 -4.6(3) . . . . ? C9 N8 C7 C2 -0.8(2) . . . . ? C41 N8 C7 C2 173.78(17) . . . . ? C5 C6 C7 N8 177.0(2) . . . . ? C5 C6 C7 C2 -1.1(3) . . . . ? N1 C2 C7 N8 0.6(2) . . . . ? C3 C2 C7 N8 -177.55(17) . . . . ? N1 C2 C7 C6 179.12(18) . . . . ? C3 C2 C7 C6 1.0(3) . . . . ? C2 N1 C9 N8 -0.4(2) . . . . ? C2 N1 C9 C29 176.63(17) . . . . ? C7 N8 C9 N1 0.8(2) . . . . ? C41 N8 C9 N1 -173.39(18) . . . . ? C7 N8 C9 C29 -176.05(18) . . . . ? C41 N8 C9 C29 9.8(3) . . . . ? C4 C3 C11 C12 108.9(2) . . . . ? C2 C3 C11 C12 -69.5(3) . . . . ? C4 C3 C11 C16 -72.7(3) . . . . ? C2 C3 C11 C16 108.9(2) . . . . ? C16 C11 C12 C13 -3.0(3) . . . . ? C3 C11 C12 C13 175.32(18) . . . . ? C16 C11 C12 C17 175.50(19) . . . . ? C3 C11 C12 C17 -6.1(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C17 C12 C13 C14 -178.1(2) . . . . ? C18 O14 C14 C15 -162.4(2) . . . . ? C18 O14 C14 C13 18.9(3) . . . . ? C12 C13 C14 O14 -179.4(2) . . . . ? C12 C13 C14 C15 1.9(3) . . . . ? O14 C14 C15 C16 179.47(19) . . . . ? C13 C14 C15 C16 -1.8(3) . . . . ? C14 C15 C16 C11 -0.8(3) . . . . ? C14 C15 C16 C19 -179.1(2) . . . . ? C12 C11 C16 C15 3.2(3) . . . . ? C3 C11 C16 C15 -175.14(19) . . . . ? C12 C11 C16 C19 -178.6(2) . . . . ? C3 C11 C16 C19 3.1(3) . . . . ? C29 N21 C22 C27 1.1(2) . . . . ? C29 N21 C22 C23 -177.0(2) . . . . ? N21 C22 C23 C24 178.3(2) . . . . ? C27 C22 C23 C24 0.3(3) . . . . ? N21 C22 C23 C31 -1.3(3) . . . . ? C27 C22 C23 C31 -179.26(19) . . . . ? C22 C23 C24 C25 1.0(3) . . . . ? C31 C23 C24 C25 -179.4(2) . . . . ? C23 C24 C25 C26 -0.9(3) . . . . ? C23 C24 C25 C30 -179.9(2) . . . . ? C24 C25 C26 C27 -0.6(3) . . . . ? C30 C25 C26 C27 178.4(2) . . . . ? C29 N28 C27 C26 179.6(2) . . . . ? C43 N28 C27 C26 -6.7(3) . . . . ? C29 N28 C27 C22 0.7(2) . . . . ? C43 N28 C27 C22 174.44(18) . . . . ? C25 C26 C27 N28 -176.8(2) . . . . ? C25 C26 C27 C22 1.9(3) . . . . ? N21 C22 C27 N28 -1.2(2) . . . . ? C23 C22 C27 N28 177.19(18) . . . . ? N21 C22 C27 C26 179.84(19) . . . . ? C23 C22 C27 C26 -1.8(3) . . . . ? C22 N21 C29 N28 -0.7(2) . . . . ? C22 N21 C29 C9 175.36(17) . . . . ? C27 N28 C29 N21 0.0(2) . . . . ? C43 N28 C29 N21 -172.85(19) . . . . ? C27 N28 C29 C9 -175.74(19) . . . . ? C43 N28 C29 C9 11.4(3) . . . . ? N1 C9 C29 N21 -13.5(3) . . . . ? N8 C9 C29 N21 163.14(18) . . . . ? N1 C9 C29 N28 161.95(19) . . . . ? N8 C9 C29 N28 -21.4(3) . . . . ? C24 C23 C31 C32 108.0(2) . . . . ? C22 C23 C31 C32 -72.4(3) . . . . ? C24 C23 C31 C36 -66.5(3) . . . . ? C22 C23 C31 C36 113.0(2) . . . . ? C36 C31 C32 C33 5.5(3) . . . . ? C23 C31 C32 C33 -169.03(19) . . . . ? C36 C31 C32 C37 -175.3(2) . . . . ? C23 C31 C32 C37 10.1(3) . . . . ? C31 C32 C33 C34 -0.8(3) . . . . ? C37 C32 C33 C34 -179.9(2) . . . . ? C38 O34 C34 C35 160.8(2) . . . . ? C38 O34 C34 C33 -19.7(3) . . . . ? C32 C33 C34 O34 175.7(2) . . . . ? C32 C33 C34 C35 -4.8(3) . . . . ? O34 C34 C35 C36 -174.9(2) . . . . ? C33 C34 C35 C36 5.6(3) . . . . ? C34 C35 C36 C31 -0.7(3) . . . . ? C34 C35 C36 C39 178.3(2) . . . . ? C32 C31 C36 C35 -4.8(3) . . . . ? C23 C31 C36 C35 169.80(19) . . . . ? C32 C31 C36 C39 176.2(2) . . . . ? C23 C31 C36 C39 -9.2(3) . . . . ? C9 N8 C41 C42 37.4(3) . . . . ? C7 N8 C41 C42 -135.82(19) . . . . ? N8 C41 C42 C43 -78.9(2) . . . . ? C29 N28 C43 C42 -27.5(3) . . . . ? C27 N28 C43 C42 160.63(18) . . . . ? C41 C42 C43 N28 67.8(2) . . . . ? # End of CIF ============================================================ # Attachment '3e.cif' data_SG0629 _database_code_depnum_ccdc_archive 'CCDC 710118' _audit_creation_method SHELXL-97 _audit_creation_date 06-08-30 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C32 H28 N4 O2' _chemical_formula_sum 'C32 H28 N4 O2' _chemical_formula_weight 500.60 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 256 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 224 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 32 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 16 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.0441(8) _cell_length_b 12.4981(5) _cell_length_c 17.4616(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.296(3) _cell_angle_gamma 90.00 _cell_volume 4976.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 4602 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 0.0850 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: DMSO Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.470(2) Frames collected: 184 Seconds exposure per frame: 66 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 30928 _diffrn_reflns_av_R_equivalents 0.1060 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.01 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 4389 _reflns_number_gt 3012 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+2.524P] 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 0.0094(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4389 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.294 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.065 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 O14 O 0.09873(9) 0.40762(15) 0.03578(11) 0.0547(6) Uani 1 1 d . . . N1 N 0.03553(8) 0.86238(15) 0.18132(11) 0.0290(5) Uani 1 1 d . . . N8 N 0.02118(8) 1.04106(15) 0.18102(11) 0.0274(5) Uani 1 1 d . . . C2 C 0.05669(10) 0.90829(19) 0.11823(13) 0.0280(6) Uani 1 1 d . . . C3 C 0.08081(10) 0.8573(2) 0.05765(14) 0.0311(6) Uani 1 1 d . . . C4 C 0.09521(10) 0.9238(2) -0.00033(14) 0.0342(6) Uani 1 1 d . . . H4 H 0.1125 0.8926 -0.0412 0.041 Uiso 1 1 calc R . . C5 C 0.08555(10) 1.0352(2) -0.00182(14) 0.0319(6) Uani 1 1 d . . . C6 C 0.06085(10) 1.0837(2) 0.05660(14) 0.0307(6) Uani 1 1 d . . . H6 H 0.0533 1.1584 0.0561 0.037 Uiso 1 1 calc R . . C7 C 0.04744(10) 1.01904(19) 0.11622(13) 0.0271(6) Uani 1 1 d . . . C9 C 0.01455(10) 0.94529(18) 0.21603(13) 0.0281(6) Uani 1 1 d . . . C10 C 0.10179(11) 1.1016(2) -0.06814(15) 0.0403(7) Uani 1 1 d . . . H101 H 0.0785 1.1675 -0.0730 0.060 Uiso 1 1 calc R . . H102 H 0.0938 1.0605 -0.1163 0.060 Uiso 1 1 calc R . . H103 H 0.1436 1.1197 -0.0580 0.060 Uiso 1 1 calc R . . C11 C 0.08631(10) 0.7394(2) 0.05461(13) 0.0322(6) Uani 1 1 d . . . C12 C 0.11051(11) 0.6797(2) 0.11784(15) 0.0386(7) Uani 1 1 d . . . H12 H 0.1241 0.7156 0.1650 0.046 Uiso 1 1 calc R . . C13 C 0.11565(11) 0.5692(2) 0.11482(16) 0.0396(7) Uani 1 1 d . . . H13 H 0.1332 0.5305 0.1590 0.048 Uiso 1 1 calc R . . C14 C 0.09495(12) 0.5161(2) 0.04702(15) 0.0397(7) Uani 1 1 d . . . C15 C 0.06791(14) 0.5734(2) -0.01614(16) 0.0517(8) Uani 1 1 d . . . H15 H 0.0515 0.5369 -0.0619 0.062 Uiso 1 1 calc R . . C16 C 0.06482(12) 0.6838(2) -0.01264(15) 0.0449(7) Uani 1 1 d . . . H16 H 0.0477 0.7225 -0.0570 0.054 Uiso 1 1 calc R . . C17 C 0.13180(13) 0.3484(2) 0.0967(2) 0.0570(9) Uani 1 1 d . . . H171 H 0.1706 0.3811 0.1101 0.085 Uiso 1 1 calc R . . H172 H 0.1363 0.2745 0.0797 0.085 Uiso 1 1 calc R . . H173 H 0.1113 0.3487 0.1421 0.085 Uiso 1 1 calc R . . C18 C -0.00207(10) 1.14149(18) 0.20598(13) 0.0303(6) Uani 1 1 d . . . H181 H -0.0435 1.1499 0.1822 0.036 Uiso 1 1 calc R . . H182 H 0.0206 1.2022 0.1892 0.036 Uiso 1 1 calc R . . O34 O 0.22370(7) 1.08088(14) 0.83177(11) 0.0437(5) Uani 1 1 d . . . N21 N 0.06718(8) 0.63707(15) 0.77951(11) 0.0300(5) Uani 1 1 d . . . N28 N 0.05553(8) 0.45833(15) 0.78830(11) 0.0310(5) Uani 1 1 d . . . C22 C 0.11986(10) 0.58970(19) 0.81294(14) 0.0294(6) Uani 1 1 d . . . C23 C 0.17408(10) 0.6378(2) 0.84238(14) 0.0309(6) Uani 1 1 d . . . C24 C 0.21695(10) 0.5679(2) 0.87760(15) 0.0355(6) Uani 1 1 d . . . H24 H 0.2539 0.5973 0.8982 0.043 Uiso 1 1 calc R . . C25 C 0.20927(11) 0.4569(2) 0.88471(15) 0.0374(6) Uani 1 1 d . . . C26 C 0.15606(10) 0.4107(2) 0.85494(14) 0.0357(6) Uani 1 1 d . . . H26 H 0.1495 0.3359 0.8585 0.043 Uiso 1 1 calc R . . C27 C 0.11304(10) 0.47868(19) 0.81982(14) 0.0314(6) Uani 1 1 d . . . C29 C 0.03099(10) 0.55521(18) 0.76712(14) 0.0295(6) Uani 1 1 d . . . C30 C 0.25862(12) 0.3893(2) 0.92465(17) 0.0508(8) Uani 1 1 d . . . H301 H 0.2507 0.3138 0.9121 0.076 Uiso 1 1 calc R . . H302 H 0.2618 0.3995 0.9808 0.076 Uiso 1 1 calc R . . H303 H 0.2955 0.4107 0.9071 0.076 Uiso 1 1 calc R . . C31 C 0.18525(10) 0.7545(2) 0.83772(13) 0.0315(6) Uani 1 1 d . . . C32 C 0.15840(10) 0.8179(2) 0.77744(14) 0.0353(6) Uani 1 1 d . . . H32 H 0.1310 0.7859 0.7382 0.042 Uiso 1 1 calc R . . C33 C 0.17026(10) 0.9263(2) 0.77268(15) 0.0361(6) Uani 1 1 d . . . H33 H 0.1517 0.9672 0.7303 0.043 Uiso 1 1 calc R . . C34 C 0.20919(10) 0.9742(2) 0.82985(15) 0.0346(6) Uani 1 1 d . . . C35 C 0.23624(11) 0.9128(2) 0.89106(15) 0.0395(7) Uani 1 1 d . . . H35 H 0.2629 0.9455 0.9308 0.047 Uiso 1 1 calc R . . C36 C 0.22484(11) 0.8058(2) 0.89449(14) 0.0377(7) Uani 1 1 d . . . H36 H 0.2443 0.7651 0.9365 0.045 Uiso 1 1 calc R . . C37 C 0.19559(12) 1.1460(2) 0.77063(16) 0.0443(7) Uani 1 1 d . . . H371 H 0.2027 1.1163 0.7209 0.067 Uiso 1 1 calc R . . H372 H 0.2114 1.2188 0.7763 0.067 Uiso 1 1 calc R . . H373 H 0.1533 1.1476 0.7726 0.067 Uiso 1 1 calc R . . C38 C 0.02332(11) 0.35728(19) 0.78521(15) 0.0362(6) Uani 1 1 d . . . H381 H 0.0049 0.3487 0.8326 0.043 Uiso 1 1 calc R . . H382 H 0.0506 0.2967 0.7822 0.043 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 O14 0.0800(14) 0.0298(12) 0.0546(13) -0.0044(10) 0.0110(11) 0.0081(10) N1 0.0335(11) 0.0247(12) 0.0285(11) 0.0000(9) 0.0038(9) 0.0014(9) N8 0.0337(11) 0.0200(11) 0.0283(11) 0.0005(9) 0.0040(9) 0.0006(8) C2 0.0290(12) 0.0255(14) 0.0289(13) 0.0023(11) 0.0023(10) -0.0017(10) C3 0.0294(13) 0.0329(15) 0.0307(14) -0.0004(11) 0.0032(11) 0.0032(11) C4 0.0314(13) 0.0405(16) 0.0314(14) -0.0006(12) 0.0067(11) 0.0040(12) C5 0.0268(13) 0.0381(16) 0.0299(14) 0.0033(12) 0.0013(10) -0.0027(11) C6 0.0301(12) 0.0260(14) 0.0347(14) 0.0031(11) 0.0005(11) -0.0035(11) C7 0.0281(12) 0.0254(14) 0.0274(13) -0.0016(10) 0.0028(10) -0.0021(10) C9 0.0307(13) 0.0224(14) 0.0303(13) 0.0021(11) 0.0010(10) -0.0006(10) C10 0.0378(14) 0.0462(18) 0.0377(15) 0.0069(13) 0.0081(12) -0.0019(12) C11 0.0362(13) 0.0296(15) 0.0322(14) -0.0027(12) 0.0093(11) 0.0027(11) C12 0.0421(15) 0.0358(16) 0.0372(15) -0.0036(13) 0.0028(12) 0.0035(12) C13 0.0418(15) 0.0351(16) 0.0414(16) 0.0031(13) 0.0039(12) 0.0044(12) C14 0.0520(16) 0.0287(16) 0.0405(16) -0.0020(13) 0.0141(13) 0.0073(12) C15 0.079(2) 0.0397(18) 0.0365(17) -0.0083(14) 0.0093(15) 0.0053(15) C16 0.0665(19) 0.0369(17) 0.0316(15) -0.0016(13) 0.0083(13) 0.0103(14) C17 0.0487(17) 0.0306(17) 0.090(2) 0.0024(16) 0.0036(16) 0.0055(13) C18 0.0362(13) 0.0236(13) 0.0307(13) -0.0004(11) 0.0036(11) 0.0002(11) O34 0.0426(10) 0.0343(11) 0.0526(12) -0.0029(9) 0.0010(9) -0.0087(8) N21 0.0284(10) 0.0228(11) 0.0376(12) -0.0010(9) 0.0006(9) -0.0005(9) N28 0.0315(11) 0.0189(11) 0.0408(13) 0.0002(9) -0.0008(9) -0.0001(9) C22 0.0293(13) 0.0254(14) 0.0333(14) 0.0005(11) 0.0033(10) 0.0019(10) C23 0.0284(13) 0.0321(15) 0.0322(14) -0.0001(11) 0.0045(10) -0.0004(11) C24 0.0274(13) 0.0378(16) 0.0399(15) -0.0005(12) 0.0002(11) 0.0017(11) C25 0.0353(14) 0.0356(16) 0.0404(16) 0.0012(12) 0.0020(12) 0.0096(12) C26 0.0382(14) 0.0274(15) 0.0405(15) -0.0014(12) 0.0023(12) 0.0054(12) C27 0.0299(13) 0.0285(14) 0.0351(14) -0.0021(11) 0.0018(11) 0.0038(11) C29 0.0313(12) 0.0208(13) 0.0359(14) 0.0000(11) 0.0029(11) 0.0023(11) C30 0.0435(16) 0.0420(18) 0.062(2) 0.0032(15) -0.0073(14) 0.0133(13) C31 0.0280(13) 0.0334(15) 0.0328(14) -0.0006(12) 0.0030(10) -0.0013(11) C32 0.0330(14) 0.0332(16) 0.0381(15) -0.0035(12) -0.0001(11) -0.0045(11) C33 0.0351(14) 0.0317(15) 0.0390(15) 0.0014(12) -0.0031(11) -0.0029(11) C34 0.0330(14) 0.0295(15) 0.0420(16) -0.0031(12) 0.0080(12) -0.0060(11) C35 0.0381(14) 0.0404(17) 0.0381(16) -0.0059(13) -0.0014(12) -0.0081(12) C36 0.0385(14) 0.0379(17) 0.0353(15) 0.0028(12) 0.0005(11) -0.0033(12) C37 0.0507(17) 0.0312(16) 0.0523(18) 0.0023(14) 0.0113(14) -0.0031(13) C38 0.0383(14) 0.0200(13) 0.0484(17) 0.0022(12) -0.0007(12) -0.0015(11) _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 O14 C14 1.374(3) . ? O14 C17 1.423(3) . ? N1 C9 1.326(3) . ? N1 C2 1.391(3) . ? N8 C9 1.363(3) . ? N8 C7 1.386(3) . ? N8 C18 1.456(3) . ? C2 C7 1.400(3) . ? C2 C3 1.415(3) . ? C3 C4 1.386(3) . ? C3 C11 1.481(3) . ? C4 C5 1.410(3) . ? C4 H4 0.9500 . ? C5 C6 1.378(3) . ? C5 C10 1.515(3) . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C9 C9 1.445(5) 2 ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 C12 1.381(3) . ? C11 C16 1.393(3) . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.386(4) . ? C15 C16 1.384(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 C18 1.527(5) 2 ? C18 H181 0.9900 . ? C18 H182 0.9900 . ? O34 C34 1.374(3) . ? O34 C37 1.422(3) . ? N21 C29 1.318(3) . ? N21 C22 1.400(3) . ? N28 C29 1.365(3) . ? N28 C27 1.383(3) . ? N28 C38 1.462(3) . ? C22 C27 1.403(3) . ? C22 C23 1.415(3) . ? C23 C24 1.394(3) . ? C23 C31 1.485(3) . ? C24 C25 1.407(3) . ? C24 H24 0.9500 . ? C25 C26 1.386(3) . ? C25 C30 1.504(3) . ? C26 C27 1.380(3) . ? C26 H26 0.9500 . ? C29 C29 1.467(5) 2_556 ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 C32 1.389(3) . ? C31 C36 1.402(3) . ? C32 C33 1.387(3) . ? C32 H32 0.9500 . ? C33 C34 1.379(3) . ? C33 H33 0.9500 . ? C34 C35 1.388(4) . ? C35 C36 1.366(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H371 0.9800 . ? C37 H372 0.9800 . ? C37 H373 0.9800 . ? C38 C38 1.512(5) 2_556 ? C38 H381 0.9900 . ? C38 H382 0.9900 . ? 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 C14 O14 C17 116.4(2) . . ? C9 N1 C2 103.43(19) . . ? C9 N8 C7 106.40(18) . . ? C9 N8 C18 123.58(19) . . ? C7 N8 C18 129.69(19) . . ? N1 C2 C7 111.0(2) . . ? N1 C2 C3 128.8(2) . . ? C7 C2 C3 120.1(2) . . ? C4 C3 C2 115.9(2) . . ? C4 C3 C11 122.6(2) . . ? C2 C3 C11 121.3(2) . . ? C3 C4 C5 123.5(2) . . ? C3 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 C10 120.0(2) . . ? C4 C5 C10 119.9(2) . . ? C5 C6 C7 117.4(2) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? N8 C7 C6 131.9(2) . . ? N8 C7 C2 105.00(19) . . ? C6 C7 C2 123.0(2) . . ? N1 C9 N8 114.2(2) . . ? N1 C9 C9 128.19(13) . 2 ? N8 C9 C9 117.64(13) . 2 ? C5 C10 H101 109.5 . . ? C5 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C5 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C12 C11 C16 117.3(2) . . ? C12 C11 C3 122.4(2) . . ? C16 C11 C3 120.3(2) . . ? C11 C12 C13 122.3(3) . . ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? O14 C14 C13 125.1(2) . . ? O14 C14 C15 115.3(2) . . ? C13 C14 C15 119.6(2) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.4(3) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? O14 C17 H171 109.5 . . ? O14 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? O14 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? N8 C18 C18 109.23(14) . 2 ? N8 C18 H181 109.8 . . ? C18 C18 H181 109.8 2 . ? N8 C18 H182 109.8 . . ? C18 C18 H182 109.8 2 . ? H181 C18 H182 108.3 . . ? C34 O34 C37 117.0(2) . . ? C29 N21 C22 103.31(19) . . ? C29 N28 C27 106.28(19) . . ? C29 N28 C38 124.63(19) . . ? C27 N28 C38 128.74(19) . . ? N21 C22 C27 110.65(19) . . ? N21 C22 C23 129.7(2) . . ? C27 C22 C23 119.6(2) . . ? C24 C23 C22 115.2(2) . . ? C24 C23 C31 121.5(2) . . ? C22 C23 C31 123.3(2) . . ? C23 C24 C25 124.6(2) . . ? C23 C24 H24 117.7 . . ? C25 C24 H24 117.7 . . ? C26 C25 C24 119.5(2) . . ? C26 C25 C30 120.6(2) . . ? C24 C25 C30 119.9(2) . . ? C27 C26 C25 116.8(2) . . ? C27 C26 H26 121.6 . . ? C25 C26 H26 121.6 . . ? C26 C27 N28 130.5(2) . . ? C26 C27 C22 124.4(2) . . ? N28 C27 C22 105.10(19) . . ? N21 C29 N28 114.6(2) . . ? N21 C29 C29 128.52(13) . 2_556 ? N28 C29 C29 116.84(13) . 2_556 ? C25 C30 H301 109.5 . . ? C25 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C25 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C32 C31 C36 116.6(2) . . ? C32 C31 C23 122.6(2) . . ? C36 C31 C23 120.7(2) . . ? C33 C32 C31 122.1(2) . . ? C33 C32 H32 118.9 . . ? C31 C32 H32 118.9 . . ? C34 C33 C32 119.6(2) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? O34 C34 C33 124.7(2) . . ? O34 C34 C35 115.9(2) . . ? C33 C34 C35 119.4(2) . . ? C36 C35 C34 120.5(2) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 121.8(2) . . ? C35 C36 H36 119.1 . . ? C31 C36 H36 119.1 . . ? O34 C37 H371 109.5 . . ? O34 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? O34 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? N28 C38 C38 109.12(16) . 2_556 ? N28 C38 H381 109.9 . . ? C38 C38 H381 109.9 2_556 . ? N28 C38 H382 109.9 . . ? C38 C38 H382 109.9 2_556 . ? H381 C38 H382 108.3 . . ? 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 C9 N1 C2 C7 -0.4(2) . . . . ? C9 N1 C2 C3 -175.7(2) . . . . ? N1 C2 C3 C4 176.4(2) . . . . ? C7 C2 C3 C4 1.5(3) . . . . ? N1 C2 C3 C11 0.3(4) . . . . ? C7 C2 C3 C11 -174.6(2) . . . . ? C2 C3 C4 C5 -1.7(3) . . . . ? C11 C3 C4 C5 174.3(2) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C3 C4 C5 C10 -179.1(2) . . . . ? C4 C5 C6 C7 1.2(3) . . . . ? C10 C5 C6 C7 -179.4(2) . . . . ? C9 N8 C7 C6 174.9(2) . . . . ? C18 N8 C7 C6 1.5(4) . . . . ? C9 N8 C7 C2 -1.8(2) . . . . ? C18 N8 C7 C2 -175.3(2) . . . . ? C5 C6 C7 N8 -177.7(2) . . . . ? C5 C6 C7 C2 -1.4(3) . . . . ? N1 C2 C7 N8 1.4(3) . . . . ? C3 C2 C7 N8 177.2(2) . . . . ? N1 C2 C7 C6 -175.7(2) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C2 N1 C9 N8 -0.8(2) . . . . ? C2 N1 C9 C9 178.1(3) . . . 2 ? C7 N8 C9 N1 1.7(3) . . . . ? C18 N8 C9 N1 175.69(19) . . . . ? C7 N8 C9 C9 -177.3(2) . . . 2 ? C18 N8 C9 C9 -3.3(4) . . . 2 ? C4 C3 C11 C12 135.4(3) . . . . ? C2 C3 C11 C12 -48.8(3) . . . . ? C4 C3 C11 C16 -47.0(3) . . . . ? C2 C3 C11 C16 128.8(3) . . . . ? C16 C11 C12 C13 2.4(4) . . . . ? C3 C11 C12 C13 -180.0(2) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C17 O14 C14 C13 -6.6(4) . . . . ? C17 O14 C14 C15 173.5(2) . . . . ? C12 C13 C14 O14 178.2(2) . . . . ? C12 C13 C14 C15 -1.8(4) . . . . ? O14 C14 C15 C16 -176.2(3) . . . . ? C13 C14 C15 C16 3.8(4) . . . . ? C14 C15 C16 C11 -2.7(4) . . . . ? C12 C11 C16 C15 -0.4(4) . . . . ? C3 C11 C16 C15 -178.1(2) . . . . ? C9 N8 C18 C18 35.7(3) . . . 2 ? C7 N8 C18 C18 -151.9(2) . . . 2 ? C29 N21 C22 C27 -0.3(3) . . . . ? C29 N21 C22 C23 -176.5(2) . . . . ? N21 C22 C23 C24 175.1(2) . . . . ? C27 C22 C23 C24 -0.8(3) . . . . ? N21 C22 C23 C31 -4.0(4) . . . . ? C27 C22 C23 C31 -180.0(2) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C31 C23 C24 C25 179.4(2) . . . . ? C23 C24 C25 C26 0.4(4) . . . . ? C23 C24 C25 C30 -179.4(2) . . . . ? C24 C25 C26 C27 -0.3(4) . . . . ? C30 C25 C26 C27 179.5(2) . . . . ? C25 C26 C27 N28 -176.7(2) . . . . ? C25 C26 C27 C22 -0.3(4) . . . . ? C29 N28 C27 C26 175.0(3) . . . . ? C38 N28 C27 C26 1.8(4) . . . . ? C29 N28 C27 C22 -1.9(3) . . . . ? C38 N28 C27 C22 -175.2(2) . . . . ? N21 C22 C27 C26 -175.8(2) . . . . ? C23 C22 C27 C26 0.9(4) . . . . ? N21 C22 C27 N28 1.4(3) . . . . ? C23 C22 C27 N28 178.0(2) . . . . ? C22 N21 C29 N28 -1.0(3) . . . . ? C22 N21 C29 C29 -179.9(3) . . . 2_556 ? C27 N28 C29 N21 1.9(3) . . . . ? C38 N28 C29 N21 175.5(2) . . . . ? C27 N28 C29 C29 -179.0(3) . . . 2_556 ? C38 N28 C29 C29 -5.4(4) . . . 2_556 ? C24 C23 C31 C32 149.7(2) . . . . ? C22 C23 C31 C32 -31.2(4) . . . . ? C24 C23 C31 C36 -29.3(3) . . . . ? C22 C23 C31 C36 149.9(2) . . . . ? C36 C31 C32 C33 0.6(4) . . . . ? C23 C31 C32 C33 -178.4(2) . . . . ? C31 C32 C33 C34 -1.0(4) . . . . ? C37 O34 C34 C33 1.0(3) . . . . ? C37 O34 C34 C35 -178.6(2) . . . . ? C32 C33 C34 O34 -179.1(2) . . . . ? C32 C33 C34 C35 0.5(4) . . . . ? O34 C34 C35 C36 -179.9(2) . . . . ? C33 C34 C35 C36 0.5(4) . . . . ? C34 C35 C36 C31 -0.9(4) . . . . ? C32 C31 C36 C35 0.4(4) . . . . ? C23 C31 C36 C35 179.4(2) . . . . ? C29 N28 C38 C38 36.5(4) . . . 2_556 ? C27 N28 C38 C38 -151.3(3) . . . 2_556 ? # End of CIF ============================================================ # Attachment '3f.cif' data_SG0706 _database_code_depnum_ccdc_archive 'CCDC 710119' _audit_creation_method SHELXL-97 _audit_creation_date 07-02-08 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C36 H36 N4 O2' _chemical_formula_sum 'C36 H36 N4 O2' _chemical_formula_weight 556.71 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 144 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 144 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 16 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 8 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 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 8.5899(4) _cell_length_b 27.0079(12) _cell_length_c 12.9677(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.886(3) _cell_angle_gamma 90.00 _cell_volume 2907.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 5132 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.0797 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: deuterochloroform / diethyl ether Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 1.315(2) Frames collected: 729 Seconds exposure per frame: 80 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 41.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 42093 _diffrn_reflns_av_R_equivalents 0.1290 _diffrn_reflns_av_sigmaI/netI 0.0937 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 5103 _reflns_number_gt 3203 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1124P)^2^+5.1383P] 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 0.0039(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5103 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1479 _refine_ls_R_factor_gt 0.0933 _refine_ls_wR_factor_ref 0.2685 _refine_ls_wR_factor_gt 0.2297 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.220 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.077 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 O14 O 1.1202(5) 0.17883(17) -0.0582(3) 0.0856(13) Uani 1 1 d . . . O34 O 0.5881(4) 0.43368(13) -0.1116(2) 0.0578(10) Uani 1 1 d . . . N1 N 0.8417(4) 0.21332(12) 0.3354(3) 0.0363(9) Uani 1 1 d . . . N8 N 0.8033(4) 0.20718(12) 0.5012(3) 0.0347(8) Uani 1 1 d . . . N21 N 0.6757(4) 0.31357(12) 0.3245(3) 0.0351(9) Uani 1 1 d . . . N28 N 0.6391(4) 0.29476(12) 0.4866(3) 0.0342(8) Uani 1 1 d . . . C2 C 0.9157(5) 0.17035(15) 0.3854(3) 0.0359(10) Uani 1 1 d . . . C3 C 1.0062(5) 0.13532(15) 0.3460(3) 0.0373(10) Uani 1 1 d . . . C4 C 1.0669(5) 0.09639(15) 0.4153(3) 0.0402(11) Uani 1 1 d . . . H4 H 1.1289 0.0717 0.3919 0.048 Uiso 1 1 calc R . . C5 C 1.0422(5) 0.09148(15) 0.5173(3) 0.0382(11) Uani 1 1 d . . . C6 C 0.9533(5) 0.12635(15) 0.5553(3) 0.0367(10) Uani 1 1 d . . . H6 H 0.9347 0.1235 0.6242 0.044 Uiso 1 1 calc R . . C7 C 0.8918(5) 0.16597(14) 0.4878(3) 0.0335(10) Uani 1 1 d . . . C9 C 0.7810(5) 0.23379(15) 0.4093(3) 0.0335(10) Uani 1 1 d . . . C10 C 1.1180(6) 0.04904(16) 0.5903(4) 0.0477(12) Uani 1 1 d . . . H101 H 1.1138 0.0564 0.6635 0.072 Uiso 1 1 calc R . . H102 H 1.2305 0.0450 0.5880 0.072 Uiso 1 1 calc R . . H103 H 1.0586 0.0184 0.5662 0.072 Uiso 1 1 calc R . . C11 C 1.0391(6) 0.14336(18) 0.2384(4) 0.0501(13) Uani 1 1 d . . . C12 C 1.1370(6) 0.1847(2) 0.2241(4) 0.0589(15) Uani 1 1 d . . . C13 C 1.1602(7) 0.1941(2) 0.1243(4) 0.0659(15) Uani 1 1 d . . . H13 H 1.2253 0.2212 0.1145 0.079 Uiso 1 1 calc R . . C14 C 1.0914(7) 0.1651(2) 0.0419(5) 0.0606(14) Uani 1 1 d . . . C15 C 0.9984(6) 0.1256(2) 0.0466(4) 0.0586(15) Uani 1 1 d . . . H15 H 0.9523 0.1062 -0.0148 0.070 Uiso 1 1 calc R . . C16 C 0.9712(7) 0.1136(2) 0.1532(4) 0.0630(15) Uani 1 1 d . . . C17 C 1.2150(7) 0.2183(2) 0.3107(4) 0.0667(15) Uani 1 1 d . . . H171 H 1.3025 0.2361 0.2909 0.100 Uiso 1 1 calc R . . H172 H 1.2589 0.1991 0.3759 0.100 Uiso 1 1 calc R . . H173 H 1.1358 0.2421 0.3232 0.100 Uiso 1 1 calc R . . C18 C 1.0631(7) 0.1504(3) -0.1462(4) 0.083(2) Uani 1 1 d . . . H181 H 1.0270 0.1185 -0.1250 0.124 Uiso 1 1 calc R . . H182 H 1.1487 0.1450 -0.1824 0.124 Uiso 1 1 calc R . . H183 H 0.9723 0.1673 -0.1948 0.124 Uiso 1 1 calc R . . C19 C 0.8697(7) 0.0706(2) 0.1654(5) 0.079(2) Uani 1 1 d . . . H191 H 0.9330 0.0401 0.1704 0.119 Uiso 1 1 calc R . . H192 H 0.7763 0.0687 0.1035 0.119 Uiso 1 1 calc R . . H193 H 0.8327 0.0747 0.2304 0.119 Uiso 1 1 calc R . . C22 C 0.5929(5) 0.35168(14) 0.3597(3) 0.0333(10) Uani 1 1 d . . . C23 C 0.5335(5) 0.39586(14) 0.3069(3) 0.0334(10) Uani 1 1 d . . . C24 C 0.4520(5) 0.42676(15) 0.3597(3) 0.0378(11) Uani 1 1 d . . . H24 H 0.4110 0.4571 0.3264 0.045 Uiso 1 1 calc R . . C25 C 0.4260(5) 0.41598(15) 0.4599(3) 0.0365(10) Uani 1 1 d . . . C26 C 0.4835(5) 0.37193(15) 0.5114(3) 0.0362(10) Uani 1 1 d . . . H26 H 0.4665 0.3637 0.5789 0.043 Uiso 1 1 calc R . . C27 C 0.5669(5) 0.34060(15) 0.4595(3) 0.0337(10) Uani 1 1 d . . . C29 C 0.6984(5) 0.28079(15) 0.4023(3) 0.0332(10) Uani 1 1 d . . . C30 C 0.3347(6) 0.45188(16) 0.5116(4) 0.0480(12) Uani 1 1 d . . . H301 H 0.2932 0.4345 0.5654 0.072 Uiso 1 1 calc R . . H302 H 0.2445 0.4659 0.4572 0.072 Uiso 1 1 calc R . . H303 H 0.4069 0.4786 0.5459 0.072 Uiso 1 1 calc R . . C31 C 0.5490(5) 0.40558(14) 0.1960(3) 0.0350(10) Uani 1 1 d . . . C32 C 0.4653(5) 0.37507(15) 0.1130(3) 0.0356(10) Uani 1 1 d . . . C33 C 0.4778(5) 0.38390(16) 0.0094(3) 0.0413(11) Uani 1 1 d . . . H33 H 0.4218 0.3632 -0.0473 0.050 Uiso 1 1 calc R . . C34 C 0.5706(6) 0.42238(17) -0.0117(3) 0.0421(11) Uani 1 1 d . . . C35 C 0.6511(6) 0.45246(16) 0.0699(4) 0.0439(11) Uani 1 1 d . . . H35 H 0.7133 0.4792 0.0545 0.053 Uiso 1 1 calc R . . C36 C 0.6439(5) 0.44476(15) 0.1743(3) 0.0418(11) Uani 1 1 d . . . C37 C 0.3573(5) 0.33389(16) 0.1324(3) 0.0412(11) Uani 1 1 d . . . H371 H 0.2909 0.3218 0.0639 0.062 Uiso 1 1 calc R . . H372 H 0.2874 0.3464 0.1755 0.062 Uiso 1 1 calc R . . H373 H 0.4235 0.3067 0.1704 0.062 Uiso 1 1 calc R . . C38 C 0.5172(7) 0.4011(2) -0.1957(4) 0.0677(16) Uani 1 1 d . . . H381 H 0.5603 0.3677 -0.1782 0.102 Uiso 1 1 calc R . . H382 H 0.5418 0.4123 -0.2616 0.102 Uiso 1 1 calc R . . H383 H 0.4002 0.4007 -0.2056 0.102 Uiso 1 1 calc R . . C39 C 0.7404(7) 0.47711(18) 0.2623(4) 0.0579(14) Uani 1 1 d . . . H391 H 0.8323 0.4911 0.2405 0.087 Uiso 1 1 calc R . . H392 H 0.7796 0.4573 0.3271 0.087 Uiso 1 1 calc R . . H393 H 0.6722 0.5040 0.2765 0.087 Uiso 1 1 calc R . . C41 C 0.7745(5) 0.22703(16) 0.6000(3) 0.0390(11) Uani 1 1 d . . . H411 H 0.8712 0.2451 0.6404 0.047 Uiso 1 1 calc R . . H412 H 0.7540 0.1995 0.6451 0.047 Uiso 1 1 calc R . . C42 C 0.6308(6) 0.26171(16) 0.5741(3) 0.0413(11) Uani 1 1 d . . . H421 H 0.5301 0.2421 0.5540 0.050 Uiso 1 1 calc R . . H422 H 0.6292 0.2815 0.6381 0.050 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 O14 0.106(3) 0.096(3) 0.063(3) 0.012(2) 0.037(2) 0.013(3) O34 0.080(3) 0.060(2) 0.039(2) 0.0082(17) 0.0246(17) 0.0033(18) N1 0.049(2) 0.0317(19) 0.0292(19) 0.0021(15) 0.0125(16) 0.0045(16) N8 0.050(2) 0.0290(19) 0.0270(19) -0.0014(15) 0.0137(16) -0.0031(16) N21 0.047(2) 0.0298(19) 0.031(2) -0.0005(15) 0.0135(16) 0.0005(16) N28 0.047(2) 0.0294(19) 0.0280(19) 0.0008(15) 0.0135(16) -0.0004(16) C2 0.047(3) 0.030(2) 0.033(2) 0.0026(18) 0.012(2) -0.0003(19) C3 0.045(3) 0.037(2) 0.029(2) -0.0028(19) 0.0085(19) 0.003(2) C4 0.052(3) 0.030(2) 0.037(3) -0.0021(19) 0.008(2) 0.000(2) C5 0.047(3) 0.025(2) 0.037(3) 0.0023(18) 0.001(2) -0.0032(19) C6 0.048(3) 0.031(2) 0.030(2) 0.0010(18) 0.009(2) -0.0054(19) C7 0.045(3) 0.024(2) 0.032(2) -0.0017(18) 0.0113(19) -0.0049(18) C9 0.047(3) 0.031(2) 0.025(2) -0.0015(18) 0.0121(19) -0.0024(19) C10 0.066(3) 0.030(2) 0.044(3) 0.006(2) 0.008(2) -0.004(2) C11 0.057(3) 0.056(3) 0.035(3) -0.004(2) 0.006(2) 0.028(3) C12 0.070(4) 0.066(4) 0.052(3) 0.033(3) 0.037(3) 0.030(3) C13 0.078(4) 0.065(4) 0.060(4) 0.010(3) 0.027(3) 0.019(3) C14 0.058(3) 0.054(3) 0.074(4) 0.003(3) 0.023(3) 0.011(3) C15 0.056(3) 0.067(4) 0.045(3) -0.017(3) -0.001(2) 0.029(3) C16 0.062(4) 0.062(4) 0.059(4) -0.010(3) 0.006(3) 0.023(3) C17 0.088(4) 0.053(3) 0.067(4) 0.011(3) 0.033(3) 0.005(3) C18 0.074(4) 0.126(6) 0.044(4) -0.004(4) 0.008(3) 0.033(4) C19 0.072(4) 0.085(4) 0.065(4) -0.035(3) -0.011(3) 0.039(4) C22 0.039(2) 0.029(2) 0.033(2) -0.0027(18) 0.0117(19) -0.0031(18) C23 0.041(2) 0.029(2) 0.031(2) -0.0051(18) 0.0095(19) -0.0014(18) C24 0.050(3) 0.025(2) 0.039(3) -0.0067(19) 0.012(2) -0.0002(19) C25 0.041(3) 0.033(2) 0.038(3) -0.0123(19) 0.013(2) -0.0050(19) C26 0.047(3) 0.036(2) 0.028(2) -0.0086(19) 0.0142(19) -0.009(2) C27 0.043(3) 0.029(2) 0.029(2) -0.0045(18) 0.0090(19) -0.0040(18) C29 0.044(3) 0.033(2) 0.026(2) -0.0016(18) 0.0156(19) -0.0018(18) C30 0.060(3) 0.040(3) 0.049(3) -0.013(2) 0.024(2) -0.001(2) C31 0.045(3) 0.026(2) 0.035(2) -0.0003(18) 0.012(2) 0.0068(19) C32 0.043(3) 0.032(2) 0.032(2) 0.0015(18) 0.0110(19) 0.0080(19) C33 0.050(3) 0.041(3) 0.034(3) -0.004(2) 0.012(2) 0.008(2) C34 0.052(3) 0.043(3) 0.033(3) 0.008(2) 0.016(2) 0.012(2) C35 0.059(3) 0.031(2) 0.046(3) 0.004(2) 0.023(2) 0.003(2) C36 0.054(3) 0.031(2) 0.043(3) 0.001(2) 0.018(2) 0.004(2) C37 0.048(3) 0.037(3) 0.039(3) -0.003(2) 0.011(2) 0.001(2) C38 0.079(4) 0.088(4) 0.037(3) 0.000(3) 0.017(3) 0.003(3) C39 0.080(4) 0.044(3) 0.054(3) -0.008(2) 0.024(3) -0.017(3) C41 0.058(3) 0.033(2) 0.029(2) 0.0033(18) 0.016(2) -0.001(2) C42 0.054(3) 0.040(3) 0.036(2) 0.000(2) 0.021(2) -0.004(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 O14 C18 1.359(7) . ? O14 C14 1.431(7) . ? O34 C34 1.376(5) . ? O34 C38 1.412(6) . ? N1 C9 1.324(5) . ? N1 C2 1.400(5) . ? N8 C9 1.363(5) . ? N8 C7 1.384(5) . ? N8 C41 1.466(5) . ? N21 C29 1.318(5) . ? N21 C22 1.393(5) . ? N28 C29 1.373(5) . ? N28 C27 1.389(5) . ? N28 C42 1.460(5) . ? C2 C7 1.400(6) . ? C2 C3 1.402(6) . ? C3 C4 1.395(6) . ? C3 C11 1.509(6) . ? C4 C5 1.399(6) . ? C4 H4 0.9500 . ? C5 C6 1.380(6) . ? C5 C10 1.522(6) . ? C6 C7 1.397(6) . ? C6 H6 0.9500 . ? C9 C29 1.445(6) . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 C16 1.369(7) . ? C11 C12 1.438(7) . ? C12 C13 1.383(7) . ? C12 C17 1.465(8) . ? C13 C14 1.335(8) . ? C13 H13 0.9500 . ? C14 C15 1.344(8) . ? C15 C16 1.495(8) . ? C15 H15 0.9500 . ? C16 C19 1.485(8) . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C22 C27 1.400(5) . ? C22 C23 1.405(6) . ? C23 C24 1.379(6) . ? C23 C31 1.502(6) . ? C24 C25 1.404(6) . ? C24 H24 0.9500 . ? C25 C26 1.391(6) . ? C25 C30 1.508(6) . ? C26 C27 1.389(6) . ? C26 H26 0.9500 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 C32 1.399(6) . ? C31 C36 1.407(6) . ? C32 C33 1.396(6) . ? C32 C37 1.511(6) . ? C33 C34 1.379(6) . ? C33 H33 0.9500 . ? C34 C35 1.372(6) . ? C35 C36 1.387(6) . ? C35 H35 0.9500 . ? C36 C39 1.506(6) . ? C37 H371 0.9800 . ? C37 H372 0.9800 . ? C37 H373 0.9800 . ? C38 H381 0.9800 . ? C38 H382 0.9800 . ? C38 H383 0.9800 . ? C39 H391 0.9800 . ? C39 H392 0.9800 . ? C39 H393 0.9800 . ? C41 C42 1.517(6) . ? C41 H411 0.9900 . ? C41 H412 0.9900 . ? C42 H421 0.9900 . ? C42 H422 0.9900 . ? 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 C18 O14 C14 120.4(5) . . ? C34 O34 C38 117.3(4) . . ? C9 N1 C2 103.1(3) . . ? C9 N8 C7 105.8(3) . . ? C9 N8 C41 123.6(3) . . ? C7 N8 C41 128.7(3) . . ? C29 N21 C22 103.5(3) . . ? C29 N28 C27 106.0(3) . . ? C29 N28 C42 123.6(3) . . ? C27 N28 C42 129.4(3) . . ? N1 C2 C7 110.5(3) . . ? N1 C2 C3 128.2(4) . . ? C7 C2 C3 121.3(4) . . ? C4 C3 C2 115.1(4) . . ? C4 C3 C11 125.2(4) . . ? C2 C3 C11 119.6(4) . . ? C3 C4 C5 124.0(4) . . ? C3 C4 H4 118.0 . . ? C5 C4 H4 118.0 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 C10 118.7(4) . . ? C4 C5 C10 121.0(4) . . ? C5 C6 C7 117.0(4) . . ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? N8 C7 C6 132.0(4) . . ? N8 C7 C2 105.7(3) . . ? C6 C7 C2 122.3(4) . . ? N1 C9 N8 114.9(4) . . ? N1 C9 C29 126.8(4) . . ? N8 C9 C29 118.3(3) . . ? C5 C10 H101 109.5 . . ? C5 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C5 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C16 C11 C12 119.6(5) . . ? C16 C11 C3 121.3(5) . . ? C12 C11 C3 119.0(4) . . ? C13 C12 C11 119.5(6) . . ? C13 C12 C17 117.1(5) . . ? C11 C12 C17 123.4(4) . . ? C14 C13 C12 120.1(6) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 125.2(6) . . ? C13 C14 O14 115.5(5) . . ? C15 C14 O14 119.3(5) . . ? C14 C15 C16 116.7(5) . . ? C14 C15 H15 121.7 . . ? C16 C15 H15 121.7 . . ? C11 C16 C19 120.8(5) . . ? C11 C16 C15 119.0(5) . . ? C19 C16 C15 120.2(5) . . ? C12 C17 H171 109.5 . . ? C12 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C12 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? O14 C18 H181 109.5 . . ? O14 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? O14 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C16 C19 H191 109.5 . . ? C16 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C16 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? N21 C22 C27 111.1(3) . . ? N21 C22 C23 128.3(4) . . ? C27 C22 C23 120.5(4) . . ? C24 C23 C22 116.0(4) . . ? C24 C23 C31 123.5(4) . . ? C22 C23 C31 120.3(3) . . ? C23 C24 C25 123.8(4) . . ? C23 C24 H24 118.1 . . ? C25 C24 H24 118.1 . . ? C26 C25 C24 120.0(4) . . ? C26 C25 C30 119.8(4) . . ? C24 C25 C30 120.1(4) . . ? C27 C26 C25 116.8(4) . . ? C27 C26 H26 121.6 . . ? C25 C26 H26 121.6 . . ? N28 C27 C26 132.2(4) . . ? N28 C27 C22 104.9(3) . . ? C26 C27 C22 122.8(4) . . ? N21 C29 N28 114.4(4) . . ? N21 C29 C9 127.7(3) . . ? N28 C29 C9 117.9(3) . . ? C25 C30 H301 109.5 . . ? C25 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C25 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C32 C31 C36 119.9(4) . . ? C32 C31 C23 118.7(4) . . ? C36 C31 C23 121.4(4) . . ? C33 C32 C31 119.3(4) . . ? C33 C32 C37 119.3(4) . . ? C31 C32 C37 121.4(4) . . ? C34 C33 C32 120.7(4) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? C35 C34 O34 116.1(4) . . ? C35 C34 C33 119.7(4) . . ? O34 C34 C33 124.2(4) . . ? C34 C35 C36 121.6(4) . . ? C34 C35 H35 119.2 . . ? C36 C35 H35 119.2 . . ? C35 C36 C31 118.8(4) . . ? C35 C36 C39 119.9(4) . . ? C31 C36 C39 121.3(4) . . ? C32 C37 H371 109.5 . . ? C32 C37 H372 109.5 . . ? H371 C37 H372 109.5 . . ? C32 C37 H373 109.5 . . ? H371 C37 H373 109.5 . . ? H372 C37 H373 109.5 . . ? O34 C38 H381 109.5 . . ? O34 C38 H382 109.5 . . ? H381 C38 H382 109.5 . . ? O34 C38 H383 109.5 . . ? H381 C38 H383 109.5 . . ? H382 C38 H383 109.5 . . ? C36 C39 H391 109.5 . . ? C36 C39 H392 109.5 . . ? H391 C39 H392 109.5 . . ? C36 C39 H393 109.5 . . ? H391 C39 H393 109.5 . . ? H392 C39 H393 109.5 . . ? N8 C41 C42 110.0(3) . . ? N8 C41 H411 109.7 . . ? C42 C41 H411 109.7 . . ? N8 C41 H412 109.7 . . ? C42 C41 H412 109.7 . . ? H411 C41 H412 108.2 . . ? N28 C42 C41 110.5(3) . . ? N28 C42 H421 109.5 . . ? C41 C42 H421 109.5 . . ? N28 C42 H422 109.5 . . ? C41 C42 H422 109.5 . . ? H421 C42 H422 108.1 . . ? 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 C9 N1 C2 C7 1.8(4) . . . . ? C9 N1 C2 C3 -176.8(4) . . . . ? N1 C2 C3 C4 179.2(4) . . . . ? C7 C2 C3 C4 0.7(6) . . . . ? N1 C2 C3 C11 2.8(7) . . . . ? C7 C2 C3 C11 -175.6(4) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? C11 C3 C4 C5 176.0(4) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C3 C4 C5 C10 -177.5(4) . . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C10 C5 C6 C7 177.1(4) . . . . ? C9 N8 C7 C6 178.4(4) . . . . ? C41 N8 C7 C6 13.9(7) . . . . ? C9 N8 C7 C2 -0.7(4) . . . . ? C41 N8 C7 C2 -165.3(4) . . . . ? C5 C6 C7 N8 -178.1(4) . . . . ? C5 C6 C7 C2 1.0(6) . . . . ? N1 C2 C7 N8 -0.7(4) . . . . ? C3 C2 C7 N8 178.0(4) . . . . ? N1 C2 C7 C6 -180.0(4) . . . . ? C3 C2 C7 C6 -1.3(6) . . . . ? C2 N1 C9 N8 -2.4(5) . . . . ? C2 N1 C9 C29 176.4(4) . . . . ? C7 N8 C9 N1 2.1(5) . . . . ? C41 N8 C9 N1 167.6(4) . . . . ? C7 N8 C9 C29 -176.8(4) . . . . ? C41 N8 C9 C29 -11.3(6) . . . . ? C4 C3 C11 C16 72.5(6) . . . . ? C2 C3 C11 C16 -111.5(5) . . . . ? C4 C3 C11 C12 -110.8(5) . . . . ? C2 C3 C11 C12 65.2(5) . . . . ? C16 C11 C12 C13 0.5(7) . . . . ? C3 C11 C12 C13 -176.3(4) . . . . ? C16 C11 C12 C17 -179.7(5) . . . . ? C3 C11 C12 C17 3.6(7) . . . . ? C11 C12 C13 C14 0.4(7) . . . . ? C17 C12 C13 C14 -179.5(5) . . . . ? C12 C13 C14 C15 -0.6(8) . . . . ? C12 C13 C14 O14 178.6(4) . . . . ? C18 O14 C14 C13 176.5(5) . . . . ? C18 O14 C14 C15 -4.3(7) . . . . ? C13 C14 C15 C16 0.0(8) . . . . ? O14 C14 C15 C16 -179.2(4) . . . . ? C12 C11 C16 C19 179.9(4) . . . . ? C3 C11 C16 C19 -3.4(7) . . . . ? C12 C11 C16 C15 -1.1(7) . . . . ? C3 C11 C16 C15 175.6(4) . . . . ? C14 C15 C16 C11 0.9(7) . . . . ? C14 C15 C16 C19 179.9(5) . . . . ? C29 N21 C22 C27 -0.2(4) . . . . ? C29 N21 C22 C23 -178.1(4) . . . . ? N21 C22 C23 C24 178.5(4) . . . . ? C27 C22 C23 C24 0.7(6) . . . . ? N21 C22 C23 C31 3.1(6) . . . . ? C27 C22 C23 C31 -174.7(4) . . . . ? C22 C23 C24 C25 -0.5(6) . . . . ? C31 C23 C24 C25 174.7(4) . . . . ? C23 C24 C25 C26 -0.2(6) . . . . ? C23 C24 C25 C30 -179.7(4) . . . . ? C24 C25 C26 C27 0.6(6) . . . . ? C30 C25 C26 C27 -179.9(4) . . . . ? C29 N28 C27 C26 177.9(4) . . . . ? C42 N28 C27 C26 9.2(7) . . . . ? C29 N28 C27 C22 -1.7(4) . . . . ? C42 N28 C27 C22 -170.4(4) . . . . ? C25 C26 C27 N28 -179.9(4) . . . . ? C25 C26 C27 C22 -0.4(6) . . . . ? N21 C22 C27 N28 1.2(4) . . . . ? C23 C22 C27 N28 179.3(4) . . . . ? N21 C22 C27 C26 -178.4(4) . . . . ? C23 C22 C27 C26 -0.3(6) . . . . ? C22 N21 C29 N28 -1.0(5) . . . . ? C22 N21 C29 C9 -179.0(4) . . . . ? C27 N28 C29 N21 1.7(5) . . . . ? C42 N28 C29 N21 171.2(4) . . . . ? C27 N28 C29 C9 179.9(3) . . . . ? C42 N28 C29 C9 -10.5(6) . . . . ? N1 C9 C29 N21 -4.3(7) . . . . ? N8 C9 C29 N21 174.4(4) . . . . ? N1 C9 C29 N28 177.7(4) . . . . ? N8 C9 C29 N28 -3.5(6) . . . . ? C24 C23 C31 C32 -109.8(5) . . . . ? C22 C23 C31 C32 65.2(5) . . . . ? C24 C23 C31 C36 69.5(6) . . . . ? C22 C23 C31 C36 -115.4(4) . . . . ? C36 C31 C32 C33 0.2(6) . . . . ? C23 C31 C32 C33 179.6(4) . . . . ? C36 C31 C32 C37 -177.6(4) . . . . ? C23 C31 C32 C37 1.7(6) . . . . ? C31 C32 C33 C34 -0.4(6) . . . . ? C37 C32 C33 C34 177.6(4) . . . . ? C38 O34 C34 C35 175.1(4) . . . . ? C38 O34 C34 C33 -5.6(6) . . . . ? C32 C33 C34 C35 -0.3(6) . . . . ? C32 C33 C34 O34 -179.5(4) . . . . ? O34 C34 C35 C36 -179.6(4) . . . . ? C33 C34 C35 C36 1.1(7) . . . . ? C34 C35 C36 C31 -1.2(7) . . . . ? C34 C35 C36 C39 177.0(4) . . . . ? C32 C31 C36 C35 0.5(6) . . . . ? C23 C31 C36 C35 -178.8(4) . . . . ? C32 C31 C36 C39 -177.7(4) . . . . ? C23 C31 C36 C39 3.0(6) . . . . ? C9 N8 C41 C42 36.1(5) . . . . ? C7 N8 C41 C42 -161.9(4) . . . . ? C29 N28 C42 C41 35.5(5) . . . . ? C27 N28 C42 C41 -157.6(4) . . . . ? N8 C41 C42 N28 -44.5(5) . . . . ? # End of CIF ============================================================