# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Namboothiri, Irishi' 'Shanbhag, Pramod' 'Nareddy, Pradeep' 'Dadwal, Mamta' _publ_contact_author_name 'Namboothiri, Irishi' _publ_contact_author_email irishi@chem.iitb.ac.in _publ_section_title ; Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes ; # Attachment '- XRay-RC-act-alk.cif' data_inn0010 _database_code_depnum_ccdc_archive 'CCDC 788174' #TrackingRef '- XRay-RC-act-alk.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 N4 O12' _chemical_formula_weight 556.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0724(4) _cell_length_b 9.7915(4) _cell_length_c 14.0849(7) _cell_angle_alpha 89.657(3) _cell_angle_beta 77.662(4) _cell_angle_gamma 82.933(3) _cell_volume 1212.75(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5505 _cell_measurement_theta_min 2.9230 _cell_measurement_theta_max 32.5206 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10904 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4233 _reflns_number_gt 3161 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1497P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4233 _refine_ls_number_parameters 441 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33074(16) 1.20949(13) 0.31982(10) 0.0409(4) Uani 1 1 d . . . O2 O 0.25009(13) 0.85602(12) 0.13673(10) 0.0313(3) Uani 1 1 d . . . O3 O 0.71543(16) 1.19744(14) 0.14896(12) 0.0481(4) Uani 1 1 d . . . O4 O 0.67614(15) 1.02129(14) 0.07187(11) 0.0413(4) Uani 1 1 d . . . O5 O 0.21783(16) 1.38862(13) 0.17539(11) 0.0423(4) Uani 1 1 d . . . O6 O 0.05641(15) 1.34953(13) 0.08885(12) 0.0482(4) Uani 1 1 d . . . O7 O 0.52033(14) 0.68146(13) 0.41523(10) 0.0355(3) Uani 1 1 d . . . O8 O 0.80708(13) 0.88976(11) 0.32727(9) 0.0277(3) Uani 1 1 d . . . O9 O 0.6096(2) 0.54134(15) 0.05897(12) 0.0593(5) Uani 1 1 d . . . O10 O 0.6304(2) 0.73550(14) 0.11810(13) 0.0615(5) Uani 1 1 d . . . O11 O 0.82754(16) 0.34939(12) 0.31265(10) 0.0386(4) Uani 1 1 d . . . O12 O 0.97738(15) 0.40011(12) 0.40376(10) 0.0375(3) Uani 1 1 d . . . N1 N 0.63737(16) 1.13628(15) 0.10725(11) 0.0276(4) Uani 1 1 d . . . N2 N 0.15644(17) 1.30973(15) 0.13282(12) 0.0295(4) Uani 1 1 d . . . N3 N 0.65652(17) 0.61143(16) 0.11388(12) 0.0319(4) Uani 1 1 d . . . N4 N 0.88920(16) 0.43368(14) 0.34972(11) 0.0273(4) Uani 1 1 d . . . C1 C 0.3453(3) 1.1603(3) 0.40944(16) 0.0453(6) Uani 1 1 d . . . C2 C 0.3892(2) 1.0273(2) 0.40486(16) 0.0414(5) Uani 1 1 d . . . C3 C 0.4048(2) 0.9866(2) 0.30692(15) 0.0347(5) Uani 1 1 d . . . C4 C 0.36805(18) 1.09901(17) 0.25818(13) 0.0235(4) Uani 1 1 d . . . C5 C 0.36476(19) 1.11894(18) 0.15351(13) 0.0235(4) Uani 1 1 d . . . C6 C 0.4845(2) 1.20725(19) 0.10068(15) 0.0279(4) Uani 1 1 d . . . C7 C 0.20722(18) 1.16256(17) 0.13472(13) 0.0227(4) Uani 1 1 d . . . C8 C 0.1057(2) 1.07924(18) 0.12338(13) 0.0228(4) Uani 1 1 d . . . C9 C 0.12024(18) 0.93224(17) 0.12125(13) 0.0237(4) Uani 1 1 d . . . C10 C 0.0262(2) 0.84605(19) 0.09819(14) 0.0303(4) Uani 1 1 d . . . C11 C 0.1011(2) 0.7111(2) 0.09832(16) 0.0361(5) Uani 1 1 d . . . C12 C 0.2335(2) 0.72162(19) 0.12178(16) 0.0367(5) Uani 1 1 d . . . C13 C 0.8316(2) 1.02378(18) 0.33475(14) 0.0305(4) Uani 1 1 d . . . C14 C 0.9570(2) 1.03330(19) 0.36830(14) 0.0320(5) Uani 1 1 d . . . C15 C 1.0174(2) 0.89782(19) 0.38406(14) 0.0309(4) Uani 1 1 d . . . C16 C 0.92465(19) 0.81249(17) 0.35787(13) 0.0255(4) Uani 1 1 d . . . C17 C 0.9339(2) 0.66584(18) 0.36128(14) 0.0258(4) Uani 1 1 d . . . C18 C 0.85117(18) 0.57905(16) 0.32951(13) 0.0234(4) Uani 1 1 d . . . C19 C 0.72379(19) 0.61265(17) 0.27622(13) 0.0243(4) Uani 1 1 d . . . C20 C 0.7506(2) 0.53831(19) 0.17840(14) 0.0277(4) Uani 1 1 d . . . C21 C 0.5705(2) 0.59403(17) 0.33707(13) 0.0252(4) Uani 1 1 d . . . C22 C 0.4657(2) 0.5105(2) 0.33202(16) 0.0371(5) Uani 1 1 d . . . C23 C 0.3416(2) 0.5467(2) 0.41137(17) 0.0403(5) Uani 1 1 d . . . C24 C 0.3786(2) 0.6485(2) 0.45963(17) 0.0418(5) Uani 1 1 d . . . H19 H 0.7239(18) 0.7092(17) 0.2609(12) 0.021(4) Uiso 1 1 d . . . H8 H 0.010(2) 1.1209(17) 0.1169(13) 0.025(5) Uiso 1 1 d . . . H20B H 0.720(2) 0.448(2) 0.1835(14) 0.036(5) Uiso 1 1 d . . . H5 H 0.400(2) 1.0272(19) 0.1222(14) 0.032(5) Uiso 1 1 d . . . H10 H -0.068(2) 0.8729(19) 0.0820(15) 0.037(5) Uiso 1 1 d . . . H17 H 1.009(2) 0.6279(17) 0.3924(13) 0.025(5) Uiso 1 1 d . . . H15 H 1.103(2) 0.8661(17) 0.4077(13) 0.023(5) Uiso 1 1 d . . . H14 H 0.997(2) 1.109(2) 0.3798(16) 0.049(6) Uiso 1 1 d . . . H13 H 0.760(2) 1.0854(19) 0.3143(13) 0.028(5) Uiso 1 1 d . . . H6B H 0.4830(19) 1.2088(17) 0.0300(14) 0.024(5) Uiso 1 1 d . . . H6A H 0.473(2) 1.301(2) 0.1310(15) 0.043(6) Uiso 1 1 d . . . H20A H 0.855(2) 0.534(2) 0.1419(15) 0.042(6) Uiso 1 1 d . . . H11 H 0.071(2) 0.630(2) 0.0814(17) 0.055(7) Uiso 1 1 d . . . H12 H 0.320(2) 0.659(2) 0.1263(16) 0.049(6) Uiso 1 1 d . . . H23 H 0.247(3) 0.509(2) 0.4292(17) 0.058(7) Uiso 1 1 d . . . H2 H 0.404(2) 0.976(2) 0.4576(17) 0.051(6) Uiso 1 1 d . . . H22 H 0.477(2) 0.441(2) 0.2837(16) 0.048(6) Uiso 1 1 d . . . H3 H 0.434(3) 0.899(2) 0.2788(18) 0.062(7) Uiso 1 1 d . . . H24 H 0.334(3) 0.708(2) 0.5162(18) 0.062(7) Uiso 1 1 d . . . H1 H 0.324(3) 1.227(3) 0.456(2) 0.071(8) Uiso 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 O1 0.0618(9) 0.0314(7) 0.0306(8) -0.0039(6) -0.0142(7) -0.0023(7) O2 0.0270(7) 0.0206(6) 0.0486(9) 0.0041(6) -0.0138(6) -0.0021(5) O3 0.0460(8) 0.0460(9) 0.0642(11) 0.0085(8) -0.0321(8) -0.0170(7) O4 0.0375(8) 0.0342(8) 0.0459(9) -0.0026(7) -0.0009(7) 0.0061(6) O5 0.0512(9) 0.0235(7) 0.0561(10) -0.0070(6) -0.0210(8) -0.0030(6) O6 0.0380(8) 0.0284(8) 0.0841(12) 0.0070(7) -0.0317(8) 0.0050(6) O7 0.0386(7) 0.0296(7) 0.0349(8) -0.0040(6) 0.0000(6) -0.0049(6) O8 0.0334(7) 0.0186(6) 0.0336(8) 0.0003(5) -0.0123(6) -0.0035(5) O9 0.0865(12) 0.0429(9) 0.0620(12) -0.0115(8) -0.0509(10) 0.0015(8) O10 0.1057(14) 0.0267(8) 0.0679(12) 0.0085(7) -0.0549(11) -0.0061(8) O11 0.0567(9) 0.0206(7) 0.0456(9) 0.0031(6) -0.0245(7) -0.0093(6) O12 0.0423(8) 0.0281(7) 0.0470(9) 0.0086(6) -0.0225(7) -0.0008(6) N1 0.0252(8) 0.0308(9) 0.0275(9) 0.0069(7) -0.0063(7) -0.0063(7) N2 0.0271(8) 0.0220(8) 0.0384(10) 0.0001(7) -0.0062(7) -0.0002(7) N3 0.0374(9) 0.0291(9) 0.0314(10) 0.0017(7) -0.0113(7) -0.0054(7) N4 0.0311(8) 0.0220(8) 0.0297(9) 0.0042(7) -0.0088(7) -0.0029(7) C1 0.0594(14) 0.0535(15) 0.0251(12) -0.0055(11) -0.0105(11) -0.0127(12) C2 0.0502(13) 0.0503(14) 0.0330(13) 0.0157(10) -0.0222(11) -0.0201(11) C3 0.0450(12) 0.0295(11) 0.0336(12) 0.0035(9) -0.0181(10) -0.0032(9) C4 0.0215(9) 0.0243(9) 0.0262(10) -0.0007(7) -0.0070(8) -0.0050(7) C5 0.0222(9) 0.0215(9) 0.0271(10) -0.0001(7) -0.0060(8) -0.0034(7) C6 0.0270(10) 0.0301(10) 0.0276(12) 0.0041(8) -0.0082(8) -0.0037(8) C7 0.0241(9) 0.0214(9) 0.0217(10) 0.0007(7) -0.0046(7) -0.0002(7) C8 0.0200(9) 0.0267(9) 0.0203(10) 0.0008(7) -0.0043(7) 0.0021(8) C9 0.0217(9) 0.0266(9) 0.0216(10) 0.0017(7) -0.0039(7) -0.0004(8) C10 0.0263(10) 0.0333(11) 0.0323(12) 0.0018(8) -0.0056(9) -0.0088(8) C11 0.0377(11) 0.0253(10) 0.0450(13) -0.0004(9) -0.0038(10) -0.0121(9) C12 0.0373(11) 0.0209(10) 0.0501(14) 0.0027(9) -0.0049(10) -0.0048(9) C13 0.0423(11) 0.0193(9) 0.0295(11) 0.0004(8) -0.0070(9) -0.0029(9) C14 0.0427(11) 0.0231(10) 0.0325(12) -0.0005(8) -0.0078(9) -0.0129(9) C15 0.0322(10) 0.0310(10) 0.0339(12) 0.0036(8) -0.0138(9) -0.0089(9) C16 0.0274(9) 0.0235(9) 0.0266(11) 0.0013(8) -0.0078(8) -0.0032(8) C17 0.0248(9) 0.0262(9) 0.0274(11) 0.0032(8) -0.0082(8) -0.0026(8) C18 0.0261(9) 0.0179(8) 0.0263(10) 0.0023(7) -0.0070(8) -0.0015(7) C19 0.0282(9) 0.0167(9) 0.0300(11) 0.0031(7) -0.0101(8) -0.0042(7) C20 0.0282(10) 0.0266(10) 0.0292(11) 0.0009(8) -0.0092(9) -0.0020(8) C21 0.0312(10) 0.0218(9) 0.0236(10) 0.0009(7) -0.0097(8) -0.0007(8) C22 0.0350(11) 0.0378(12) 0.0412(13) -0.0008(10) -0.0089(10) -0.0140(9) C23 0.0279(11) 0.0438(13) 0.0488(14) 0.0136(11) -0.0066(10) -0.0063(9) C24 0.0370(12) 0.0390(12) 0.0414(14) 0.0086(10) 0.0046(10) 0.0028(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.354(2) . ? O1 C1 1.375(3) . ? O2 C12 1.365(2) . ? O2 C9 1.373(2) . ? O3 N1 1.2214(19) . ? O4 N1 1.2141(19) . ? O5 N2 1.2331(19) . ? O6 N2 1.2285(19) . ? O7 C21 1.361(2) . ? O7 C24 1.380(2) . ? O8 C13 1.366(2) . ? O8 C16 1.375(2) . ? O9 N3 1.212(2) . ? O10 N3 1.2081(19) . ? O11 N4 1.2290(18) . ? O12 N4 1.2328(19) . ? N1 C6 1.494(2) . ? N2 C7 1.460(2) . ? N3 C20 1.497(2) . ? N4 C18 1.464(2) . ? C1 C2 1.312(3) . ? C1 H1 0.90(3) . ? C2 C3 1.411(3) . ? C2 H2 0.92(2) . ? C3 C4 1.339(3) . ? C3 H3 0.93(2) . ? C4 C5 1.492(2) . ? C5 C7 1.518(2) . ? C5 C6 1.536(2) . ? C5 H5 0.988(18) . ? C6 H6B 0.999(19) . ? C6 H6A 1.00(2) . ? C7 C8 1.338(2) . ? C8 C9 1.429(2) . ? C8 H8 0.932(18) . ? C9 C10 1.358(2) . ? C10 C11 1.410(3) . ? C10 H10 0.94(2) . ? C11 C12 1.328(3) . ? C11 H11 0.92(2) . ? C12 H12 0.95(2) . ? C13 C14 1.335(3) . ? C13 H13 0.923(19) . ? C14 C15 1.407(3) . ? C14 H14 0.90(2) . ? C15 C16 1.360(2) . ? C15 H15 0.930(18) . ? C16 C17 1.429(2) . ? C17 C18 1.339(2) . ? C17 H17 0.929(18) . ? C18 C19 1.510(2) . ? C19 C21 1.501(2) . ? C19 C20 1.521(3) . ? C19 H19 0.969(17) . ? C20 H20B 0.960(19) . ? C20 H20A 0.98(2) . ? C21 C22 1.341(2) . ? C22 C23 1.418(3) . ? C22 H22 0.94(2) . ? C23 C24 1.325(3) . ? C23 H23 0.96(2) . ? C24 H24 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C1 105.78(15) . . ? C12 O2 C9 106.15(14) . . ? C21 O7 C24 106.00(15) . . ? C13 O8 C16 105.79(14) . . ? O4 N1 O3 123.91(15) . . ? O4 N1 C6 118.40(15) . . ? O3 N1 C6 117.69(16) . . ? O6 N2 O5 123.07(15) . . ? O6 N2 C7 119.17(15) . . ? O5 N2 C7 117.76(15) . . ? O10 N3 O9 122.85(17) . . ? O10 N3 C20 119.80(16) . . ? O9 N3 C20 117.35(15) . . ? O11 N4 O12 122.55(14) . . ? O11 N4 C18 117.35(14) . . ? O12 N4 C18 120.08(14) . . ? C2 C1 O1 111.12(19) . . ? C2 C1 H1 136.0(18) . . ? O1 C1 H1 112.9(17) . . ? C1 C2 C3 106.09(19) . . ? C1 C2 H2 123.5(14) . . ? C3 C2 H2 130.4(14) . . ? C4 C3 C2 107.48(19) . . ? C4 C3 H3 124.2(15) . . ? C2 C3 H3 128.3(15) . . ? C3 C4 O1 109.53(17) . . ? C3 C4 C5 131.51(18) . . ? O1 C4 C5 118.96(15) . . ? C4 C5 C7 114.18(15) . . ? C4 C5 C6 113.39(14) . . ? C7 C5 C6 113.21(14) . . ? C4 C5 H5 105.1(11) . . ? C7 C5 H5 106.7(10) . . ? C6 C5 H5 103.0(10) . . ? N1 C6 C5 107.66(14) . . ? N1 C6 H6B 105.9(10) . . ? C5 C6 H6B 109.2(10) . . ? N1 C6 H6A 107.8(11) . . ? C5 C6 H6A 112.5(11) . . ? H6B C6 H6A 113.3(15) . . ? C8 C7 N2 115.61(15) . . ? C8 C7 C5 126.48(15) . . ? N2 C7 C5 117.85(14) . . ? C7 C8 C9 129.26(16) . . ? C7 C8 H8 117.0(10) . . ? C9 C8 H8 113.7(10) . . ? C10 C9 O2 109.13(15) . . ? C10 C9 C8 130.03(17) . . ? O2 C9 C8 120.64(15) . . ? C9 C10 C11 106.97(17) . . ? C9 C10 H10 125.7(12) . . ? C11 C10 H10 127.3(12) . . ? C12 C11 C10 106.75(17) . . ? C12 C11 H11 124.7(14) . . ? C10 C11 H11 128.4(14) . . ? C11 C12 O2 111.00(18) . . ? C11 C12 H12 135.1(13) . . ? O2 C12 H12 113.7(13) . . ? C14 C13 O8 111.33(17) . . ? C14 C13 H13 135.4(11) . . ? O8 C13 H13 113.3(11) . . ? C13 C14 C15 106.42(16) . . ? C13 C14 H14 128.5(14) . . ? C15 C14 H14 125.1(14) . . ? C16 C15 C14 107.17(17) . . ? C16 C15 H15 123.0(10) . . ? C14 C15 H15 129.8(10) . . ? C15 C16 O8 109.28(15) . . ? C15 C16 C17 129.57(17) . . ? O8 C16 C17 121.12(15) . . ? C18 C17 C16 130.69(17) . . ? C18 C17 H17 117.3(11) . . ? C16 C17 H17 112.0(11) . . ? C17 C18 N4 115.46(15) . . ? C17 C18 C19 128.13(15) . . ? N4 C18 C19 116.40(14) . . ? C21 C19 C18 113.04(15) . . ? C21 C19 C20 110.93(14) . . ? C18 C19 C20 113.86(14) . . ? C21 C19 H19 108.1(10) . . ? C18 C19 H19 105.3(10) . . ? C20 C19 H19 105.0(10) . . ? N3 C20 C19 111.22(15) . . ? N3 C20 H20B 104.0(11) . . ? C19 C20 H20B 113.0(12) . . ? N3 C20 H20A 105.2(12) . . ? C19 C20 H20A 113.0(12) . . ? H20B C20 H20A 109.8(17) . . ? C22 C21 O7 109.93(17) . . ? C22 C21 C19 134.64(18) . . ? O7 C21 C19 115.43(14) . . ? C21 C22 C23 107.05(19) . . ? C21 C22 H22 124.4(13) . . ? C23 C22 H22 128.6(13) . . ? C24 C23 C22 106.58(18) . . ? C24 C23 H23 124.1(14) . . ? C22 C23 H23 129.4(14) . . ? C23 C24 O7 110.43(19) . . ? C23 C24 H24 138.6(14) . . ? O7 C24 H24 110.9(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O1 C1 C2 0.1(2) . . . . ? O1 C1 C2 C3 0.1(3) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 O1 0.4(2) . . . . ? C2 C3 C4 C5 179.43(17) . . . . ? C1 O1 C4 C3 -0.3(2) . . . . ? C1 O1 C4 C5 -179.48(16) . . . . ? C3 C4 C5 C7 115.2(2) . . . . ? O1 C4 C5 C7 -65.89(19) . . . . ? C3 C4 C5 C6 -113.1(2) . . . . ? O1 C4 C5 C6 65.8(2) . . . . ? O4 N1 C6 C5 60.4(2) . . . . ? O3 N1 C6 C5 -118.90(17) . . . . ? C4 C5 C6 N1 59.9(2) . . . . ? C7 C5 C6 N1 -167.94(15) . . . . ? O6 N2 C7 C8 -25.7(2) . . . . ? O5 N2 C7 C8 154.83(17) . . . . ? O6 N2 C7 C5 156.91(17) . . . . ? O5 N2 C7 C5 -22.6(2) . . . . ? C4 C5 C7 C8 -86.0(2) . . . . ? C6 C5 C7 C8 142.27(19) . . . . ? C4 C5 C7 N2 91.10(18) . . . . ? C6 C5 C7 N2 -40.7(2) . . . . ? N2 C7 C8 C9 179.60(17) . . . . ? C5 C7 C8 C9 -3.3(3) . . . . ? C12 O2 C9 C10 0.5(2) . . . . ? C12 O2 C9 C8 -174.94(16) . . . . ? C7 C8 C9 C10 -171.0(2) . . . . ? C7 C8 C9 O2 3.4(3) . . . . ? O2 C9 C10 C11 -0.6(2) . . . . ? C8 C9 C10 C11 174.24(18) . . . . ? C9 C10 C11 C12 0.5(2) . . . . ? C10 C11 C12 O2 -0.2(2) . . . . ? C9 O2 C12 C11 -0.2(2) . . . . ? C16 O8 C13 C14 -0.1(2) . . . . ? O8 C13 C14 C15 -0.3(2) . . . . ? C13 C14 C15 C16 0.6(2) . . . . ? C14 C15 C16 O8 -0.7(2) . . . . ? C14 C15 C16 C17 -178.87(19) . . . . ? C13 O8 C16 C15 0.5(2) . . . . ? C13 O8 C16 C17 178.89(16) . . . . ? C15 C16 C17 C18 -174.4(2) . . . . ? O8 C16 C17 C18 7.6(3) . . . . ? C16 C17 C18 N4 -177.27(18) . . . . ? C16 C17 C18 C19 2.4(3) . . . . ? O11 N4 C18 C17 -172.25(16) . . . . ? O12 N4 C18 C17 9.3(2) . . . . ? O11 N4 C18 C19 8.1(2) . . . . ? O12 N4 C18 C19 -170.42(15) . . . . ? C17 C18 C19 C21 -109.4(2) . . . . ? N4 C18 C19 C21 70.2(2) . . . . ? C17 C18 C19 C20 122.8(2) . . . . ? N4 C18 C19 C20 -57.6(2) . . . . ? O10 N3 C20 C19 33.9(2) . . . . ? O9 N3 C20 C19 -146.10(18) . . . . ? C21 C19 C20 N3 72.68(18) . . . . ? C18 C19 C20 N3 -158.47(14) . . . . ? C24 O7 C21 C22 0.3(2) . . . . ? C24 O7 C21 C19 179.15(15) . . . . ? C18 C19 C21 C22 -115.8(2) . . . . ? C20 C19 C21 C22 13.5(3) . . . . ? C18 C19 C21 O7 65.66(19) . . . . ? C20 C19 C21 O7 -165.05(14) . . . . ? O7 C21 C22 C23 0.0(2) . . . . ? C19 C21 C22 C23 -178.55(19) . . . . ? C21 C22 C23 C24 -0.3(2) . . . . ? C22 C23 C24 O7 0.5(2) . . . . ? C21 O7 C24 C23 -0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.246 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.039