# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_7606sadabs _audit_block_code GUl-GB-471-01 _audit_creation_date 2011-11-08 _audit_creation_method ; Olex2 1.1 (compiled 2011.09.07 svn.r1971, GUI svn.r3853) ; _chemical_name_common ? _chemical_name_systematic ; Title ; _chemical_compound_source dimethylsulfoxid _chemical_formula_moiety 'C19 H16 N2 O3 S, C2 H6 O S' _chemical_formula_sum 'C21 H22 N2 O4 S2' _chemical_formula_weight 430.53 _chemical_melting_point ? 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-p 2yn' _symmetry_Int_Tables_number 14 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.338(2) _cell_length_b 7.9222(17) _cell_length_c 22.498(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.389(4) _cell_angle_gamma 90.00 _cell_volume 2014.9(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9744 _cell_measurement_temperature 100 _cell_measurement_theta_max 34.9642 _cell_measurement_theta_min 2.7267 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_T_max 0.98983 _exptl_absorpt_correction_T_min 0.95788 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 0.00 0.1290 0.00 1.00 0.00 0.1310 1.00 0.00 0.00 0.0920 -1.00 0.00 0.00 0.1110 0.00 0.00 -1.00 0.0280 0.00 0.00 1.00 0.0330 _exptl_crystal_description plate _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.203 _exptl_crystal_size_min 0.061 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0172 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 70025 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 35.06 _diffrn_reflns_theta_min 1.82 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 66.67 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker-AXS Kappa Mach3 APEX-II' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator 'Incoatec Helios mirrors' _diffrn_radiation_type Mo-K\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 7748 _reflns_number_total 8855 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _refine_diff_density_max 1.230 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.073 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 268 _refine_ls_number_reflns 8855 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0434 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+1.3904P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1124 _refine_ls_wR_factor_ref 0.1176 _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. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.9219 and 1.0000 (SADABS). Highest peak ? Deepest hole ? ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.59291(2) 0.50985(3) 0.095329(12) 0.01432(6) Uani 1 1 d . . . S2 S 0.77860(3) 0.97434(4) 0.167038(13) 0.01917(7) Uani 1 1 d . . . O1 O 0.73458(8) 0.16653(11) 0.01138(4) 0.01939(16) Uani 1 1 d . . . O2 O 0.65264(9) 0.57517(12) 0.14896(4) 0.02161(17) Uani 1 1 d . . . O3 O 0.51499(8) 0.62309(11) 0.06139(4) 0.01997(16) Uani 1 1 d . . . O4 O 0.80336(10) 1.16072(12) 0.16844(5) 0.0274(2) Uani 1 1 d . . . N1 N 0.92775(8) 0.41899(12) 0.11684(4) 0.01523(16) Uani 1 1 d . . . H1 H 0.8881(19) 0.332(3) 0.1290(10) 0.035(5) Uiso 1 1 d . . . N2 N 0.69029(8) 0.42323(11) 0.05267(4) 0.01306(15) Uani 1 1 d . . . C1 C 1.03210(9) 0.47524(14) 0.14540(5) 0.01455(17) Uani 1 1 d . . . C2 C 1.10022(10) 0.40681(16) 0.19396(5) 0.01825(19) Uani 1 1 d . . . H2 H 1.0768 0.3093 0.2129 0.022 Uiso 1 1 calc R . . C3 C 1.20448(10) 0.49040(17) 0.21291(5) 0.0198(2) Uani 1 1 d . . . H3 H 1.2514 0.4484 0.2453 0.024 Uiso 1 1 calc R . . C4 C 1.24009(10) 0.63691(17) 0.18404(6) 0.0203(2) Uani 1 1 d . . . H4 H 1.3107 0.6892 0.1974 0.024 Uiso 1 1 calc R . . C5 C 1.17222(10) 0.70528(15) 0.13612(6) 0.01833(19) Uani 1 1 d . . . H5 H 1.1965 0.8025 0.1174 0.022 Uiso 1 1 calc R . . C6 C 1.06611(9) 0.62473(14) 0.11646(5) 0.01391(17) Uani 1 1 d . . . C7 C 0.97588(9) 0.65982(13) 0.07008(5) 0.01385(17) Uani 1 1 d . . . C8 C 0.96257(10) 0.80595(14) 0.02799(5) 0.01731(19) Uani 1 1 d . . . H8A H 1.0361 0.8232 0.0094 0.021 Uiso 1 1 calc R . . H8B H 0.9460 0.9075 0.0500 0.021 Uiso 1 1 calc R . . C9 C 0.86214(10) 0.77462(15) -0.02033(5) 0.01706(19) Uani 1 1 d . . . H9A H 0.8382 0.8813 -0.0386 0.020 Uiso 1 1 calc R . . H9B H 0.8908 0.7027 -0.0510 0.020 Uiso 1 1 calc R . . C10 C 0.75510(10) 0.69142(14) 0.00474(5) 0.01671(18) Uani 1 1 d . . . H10A H 0.6910 0.6829 -0.0263 0.020 Uiso 1 1 calc R . . H10B H 0.7282 0.7599 0.0368 0.020 Uiso 1 1 calc R . . C11 C 0.78865(9) 0.51531(13) 0.02824(5) 0.01388(17) Uani 1 1 d . . . H11 H 0.8133 0.4495 -0.0056 0.017 Uiso 1 1 calc R . . C12 C 0.89465(9) 0.53213(13) 0.07196(5) 0.01368(17) Uani 1 1 d . . . C13 C 0.67296(9) 0.25105(13) 0.04143(5) 0.01466(17) Uani 1 1 d . . . C14 C 0.57135(9) 0.19132(13) 0.07371(5) 0.01288(16) Uani 1 1 d . . . C15 C 0.52628(10) 0.02848(14) 0.07376(5) 0.01600(18) Uani 1 1 d . . . H15 H 0.5595 -0.0574 0.0523 0.019 Uiso 1 1 calc R . . C16 C 0.42965(10) -0.00243(15) 0.10692(6) 0.0190(2) Uani 1 1 d . . . H16 H 0.3975 -0.1104 0.1074 0.023 Uiso 1 1 calc R . . C17 C 0.38044(10) 0.12617(16) 0.13941(6) 0.0201(2) Uani 1 1 d . . . H17 H 0.3161 0.1025 0.1613 0.024 Uiso 1 1 calc R . . C18 C 0.42618(10) 0.28973(16) 0.13957(5) 0.0187(2) Uani 1 1 d . . . H18 H 0.3937 0.3762 0.1610 0.022 Uiso 1 1 calc R . . C19 C 0.52227(9) 0.31742(13) 0.10627(5) 0.01367(17) Uani 1 1 d . . . C20 C 0.67566(12) 0.94075(17) 0.22201(6) 0.0230(2) Uani 1 1 d . . . H20A H 0.7079 0.9842 0.2597 0.035 Uiso 1 1 calc R . . H20B H 0.6608 0.8220 0.2256 0.035 Uiso 1 1 calc R . . H20C H 0.6029 0.9980 0.2103 0.035 Uiso 1 1 calc R . . C21 C 0.90266(16) 0.8761(2) 0.20648(8) 0.0371(4) Uani 1 1 d . . . H21A H 0.9724 0.8964 0.1859 0.056 Uiso 1 1 calc R . . H21B H 0.8891 0.7567 0.2088 0.056 Uiso 1 1 calc R . . H21C H 0.9133 0.9222 0.2460 0.056 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 S1 0.01588(11) 0.01061(10) 0.01664(12) -0.00172(8) 0.00235(8) -0.00094(8) S2 0.02765(14) 0.01500(12) 0.01520(12) 0.00036(9) 0.00390(10) -0.00214(10) O1 0.0183(4) 0.0156(4) 0.0253(4) -0.0034(3) 0.0081(3) -0.0006(3) O2 0.0268(4) 0.0183(4) 0.0197(4) -0.0066(3) 0.0013(3) -0.0047(3) O3 0.0197(4) 0.0138(3) 0.0267(4) 0.0024(3) 0.0034(3) 0.0033(3) O4 0.0373(5) 0.0153(4) 0.0305(5) 0.0046(3) 0.0075(4) -0.0073(4) N1 0.0137(3) 0.0139(4) 0.0180(4) 0.0041(3) 0.0002(3) -0.0018(3) N2 0.0121(3) 0.0105(3) 0.0167(4) -0.0003(3) 0.0023(3) -0.0022(3) C1 0.0125(4) 0.0157(4) 0.0155(4) 0.0014(3) 0.0014(3) 0.0002(3) C2 0.0163(4) 0.0227(5) 0.0157(4) 0.0026(4) 0.0011(3) 0.0025(4) C3 0.0165(4) 0.0267(6) 0.0160(5) -0.0026(4) -0.0006(4) 0.0040(4) C4 0.0145(4) 0.0226(5) 0.0232(5) -0.0056(4) -0.0015(4) 0.0000(4) C5 0.0133(4) 0.0169(5) 0.0246(5) -0.0018(4) 0.0003(4) -0.0024(3) C6 0.0119(4) 0.0132(4) 0.0166(4) -0.0008(3) 0.0014(3) -0.0011(3) C7 0.0127(4) 0.0115(4) 0.0174(4) 0.0020(3) 0.0013(3) -0.0020(3) C8 0.0156(4) 0.0137(4) 0.0226(5) 0.0052(4) 0.0019(4) -0.0026(3) C9 0.0180(4) 0.0162(4) 0.0171(4) 0.0050(4) 0.0024(4) -0.0022(3) C10 0.0146(4) 0.0162(4) 0.0191(5) 0.0054(4) -0.0001(3) -0.0012(3) C11 0.0129(4) 0.0127(4) 0.0162(4) 0.0014(3) 0.0016(3) -0.0023(3) C12 0.0122(4) 0.0122(4) 0.0165(4) 0.0025(3) 0.0007(3) -0.0015(3) C13 0.0130(4) 0.0106(4) 0.0208(5) -0.0023(3) 0.0044(3) -0.0026(3) C14 0.0129(4) 0.0115(4) 0.0143(4) 0.0002(3) 0.0012(3) -0.0015(3) C15 0.0166(4) 0.0119(4) 0.0196(5) 0.0000(3) 0.0015(4) -0.0027(3) C16 0.0177(4) 0.0165(5) 0.0228(5) 0.0036(4) 0.0020(4) -0.0051(4) C17 0.0164(4) 0.0229(5) 0.0218(5) 0.0048(4) 0.0054(4) -0.0030(4) C18 0.0176(4) 0.0197(5) 0.0198(5) 0.0004(4) 0.0068(4) 0.0001(4) C19 0.0139(4) 0.0119(4) 0.0153(4) -0.0002(3) 0.0022(3) -0.0002(3) C20 0.0291(6) 0.0201(5) 0.0205(5) 0.0004(4) 0.0058(4) -0.0058(4) C21 0.0374(8) 0.0419(9) 0.0327(7) 0.0047(6) 0.0071(6) 0.0192(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4342(10) . ? S1 O3 1.4371(9) . ? S1 N2 1.6654(10) . ? S1 C19 1.7483(11) . ? S2 O4 1.5029(11) . ? S2 C20 1.7843(13) . ? S2 C21 1.7837(17) . ? O1 C13 1.2108(13) . ? N1 C1 1.3765(14) . ? N1 C12 1.3806(14) . ? N2 C11 1.4735(14) . ? N2 C13 1.3984(14) . ? C1 C2 1.3981(16) . ? C1 C6 1.4191(15) . ? C2 C3 1.3931(17) . ? C3 C4 1.4043(19) . ? C4 C5 1.3860(17) . ? C5 C6 1.4031(15) . ? C6 C7 1.4316(15) . ? C7 C8 1.4959(15) . ? C7 C12 1.3709(14) . ? C8 C9 1.5331(17) . ? C9 C10 1.5266(16) . ? C10 C11 1.5298(16) . ? C11 C12 1.4996(15) . ? C13 C14 1.4856(15) . ? C14 C15 1.3876(15) . ? C14 C19 1.3808(15) . ? C15 C16 1.3935(16) . ? C16 C17 1.3950(18) . ? C17 C18 1.3956(18) . ? C18 C19 1.3860(15) . ? 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 O2 S1 O3 116.95(6) . . ? O2 S1 N2 110.01(5) . . ? O2 S1 C19 112.84(6) . . ? O3 S1 N2 111.02(5) . . ? O3 S1 C19 110.46(5) . . ? N2 S1 C19 93.04(5) . . ? O4 S2 C20 105.25(6) . . ? O4 S2 C21 106.23(9) . . ? C21 S2 C20 97.06(8) . . ? C1 N1 C12 107.88(9) . . ? C11 N2 S1 124.40(7) . . ? C13 N2 S1 114.58(7) . . ? C13 N2 C11 121.02(9) . . ? N1 C1 C2 130.01(10) . . ? N1 C1 C6 108.06(9) . . ? C2 C1 C6 121.93(10) . . ? C3 C2 C1 117.38(11) . . ? C2 C3 C4 121.24(11) . . ? C5 C4 C3 121.37(11) . . ? C4 C5 C6 118.63(11) . . ? C1 C6 C7 107.00(9) . . ? C5 C6 C1 119.44(10) . . ? C5 C6 C7 133.56(10) . . ? C6 C7 C8 130.06(9) . . ? C12 C7 C6 106.18(9) . . ? C12 C7 C8 123.72(10) . . ? C7 C8 C9 110.92(9) . . ? C10 C9 C8 112.11(9) . . ? C9 C10 C11 109.74(9) . . ? N2 C11 C10 113.90(9) . . ? N2 C11 C12 113.01(9) . . ? C12 C11 C10 108.13(9) . . ? N1 C12 C11 125.55(9) . . ? C7 C12 N1 110.85(9) . . ? C7 C12 C11 123.51(10) . . ? O1 C13 N2 124.15(10) . . ? O1 C13 C14 126.81(10) . . ? N2 C13 C14 109.01(9) . . ? C15 C14 C13 126.58(10) . . ? C19 C14 C13 112.83(9) . . ? C19 C14 C15 120.59(10) . . ? C14 C15 C16 117.93(10) . . ? C15 C16 C17 120.97(11) . . ? C16 C17 C18 121.06(10) . . ? C19 C18 C17 116.93(11) . . ? C14 C19 S1 110.40(8) . . ? C14 C19 C18 122.52(10) . . ? C18 C19 S1 126.99(9) . . ? _database_code_depnum_ccdc_archive 'CCDC 914987' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment 'web_deposit_cif_file_1_JoergRust_1355128984.7642.cif' data_7642sadabs _audit_creation_date 2011-12-19 _audit_block_code GUL-GC-528-01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Title ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source dimethylsulfoxid _chemical_formula_moiety 'C19 H16 Cl N3 , C2 H6 O S' _chemical_formula_sum 'C21 H22 Cl N3 O S' _chemical_formula_weight 399.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3396(3) _cell_length_b 11.1324(3) _cell_length_c 18.1230(5) _cell_angle_alpha 83.171(2) _cell_angle_beta 75.762(2) _cell_angle_gamma 89.106(2) _cell_volume 2007.42(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 6505 _cell_measurement_theta_min 3.9997 _cell_measurement_theta_max 63.8067 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.1310 0.00 -1.00 0.00 0.1680 1.00 0.00 0.00 0.1640 -1.00 0.00 0.00 0.1670 0.00 0.00 -1.00 0.0540 0.00 0.00 1.00 0.0270 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.777 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.60398 _exptl_absorpt_correction_T_max 0.87281 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type Cu-K\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'focusing multilayer optic' _diffrn_measurement_device_type 'Bruker AXS X8 Proteum' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 66.67 _diffrn_reflns_number 41515 _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 64.60 _reflns_number_total 6514 _reflns_number_gt 5028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROTEUM2 (Bruker AXS, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.4884 and 0.9254 (SADABS). Highest peak 0.24 at 0.6852 0.3839 0.2652 [ 0.68 A from H5 ] Deepest hole -0.37 at 0.6152 0.3267 0.2861 [ 0.29 A from H5 ] _iucr_refine_instructions_details ; _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^)+(0.0343P)^2^+1.6515P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6514 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2858(3) 0.5661(2) 0.11103(15) 0.0272(6) Uani 1 1 d . . . C2 C 0.3207(2) 0.4531(2) 0.08936(15) 0.0248(6) Uani 1 1 d . . . H2 H 0.3989 0.4418 0.0526 0.030 Uiso 1 1 calc R . . C3 C 0.2339(2) 0.3554(2) 0.12468(15) 0.0231(5) Uani 1 1 d . . . C4 C 0.2371(2) 0.2283(2) 0.11873(15) 0.0238(5) Uani 1 1 d . . . C5 C 0.3386(2) 0.1538(2) 0.07002(15) 0.0270(6) Uani 1 1 d . . . H5B H 0.4276 0.1772 0.0719 0.032 Uiso 1 1 calc R . . H5A H 0.3324 0.1685 0.0172 0.032 Uiso 1 1 calc R . . C6 C 0.3144(3) 0.0191(2) 0.09896(16) 0.0300(6) Uani 1 1 d . . . H6A H 0.3641 -0.0285 0.0602 0.036 Uiso 1 1 calc R . . H6B H 0.3471 0.0002 0.1447 0.036 Uiso 1 1 calc R . . C7 C 0.1666(3) -0.0153(2) 0.11727(16) 0.0296(6) Uani 1 1 d . . . H7B H 0.1563 -0.1021 0.1313 0.036 Uiso 1 1 calc R . . H7A H 0.1334 0.0054 0.0718 0.036 Uiso 1 1 calc R . . C8 C 0.0834(2) 0.0493(2) 0.18271(15) 0.0248(6) Uani 1 1 d . . . H8 H -0.0109 0.0427 0.1826 0.030 Uiso 1 1 calc R . . C9 C 0.1234(2) 0.1798(2) 0.16834(14) 0.0236(5) Uani 1 1 d . . . C10 C 0.1158(2) 0.3774(2) 0.17976(15) 0.0250(6) Uani 1 1 d . . . C11 C 0.0819(3) 0.4920(2) 0.20073(15) 0.0286(6) Uani 1 1 d . . . H11 H 0.0036 0.5045 0.2371 0.034 Uiso 1 1 calc R . . C12 C 0.1687(3) 0.5874(2) 0.16555(16) 0.0288(6) Uani 1 1 d . . . H12 H 0.1490 0.6653 0.1782 0.035 Uiso 1 1 calc R . . C13 C 0.0486(2) -0.1092(2) 0.29625(14) 0.0233(5) Uani 1 1 d . . . C14 C -0.0488(2) -0.1742(2) 0.27362(15) 0.0258(6) Uani 1 1 d . . . H14 H -0.0785 -0.1438 0.2308 0.031 Uiso 1 1 calc R . . C15 C -0.0998(2) -0.2827(2) 0.31488(15) 0.0265(6) Uani 1 1 d . . . H15 H -0.1647 -0.3239 0.2999 0.032 Uiso 1 1 calc R . . C16 C -0.0554(2) -0.3313(2) 0.37858(15) 0.0265(6) Uani 1 1 d . . . C17 C 0.0412(3) -0.2674(2) 0.40173(15) 0.0277(6) Uani 1 1 d . . . H17 H 0.0716 -0.2989 0.4442 0.033 Uiso 1 1 calc R . . C18 C 0.0907(2) -0.1584(2) 0.36152(15) 0.0267(6) Uani 1 1 d . . . H18 H 0.1534 -0.1162 0.3779 0.032 Uiso 1 1 calc R . . C19 C -0.1044(3) -0.4472(2) 0.41952(16) 0.0306(6) Uani 1 1 d . . . C20 C 0.7861(3) 0.8916(2) 0.11292(15) 0.0278(6) Uani 1 1 d . . . C21 C 0.8185(2) 1.0122(2) 0.09146(15) 0.0262(6) Uani 1 1 d . . . H21 H 0.8970 1.0361 0.0551 0.031 Uiso 1 1 calc R . . C22 C 0.7305(2) 1.0981(2) 0.12570(15) 0.0252(6) Uani 1 1 d . . . C23 C 0.7314(2) 1.2273(2) 0.11957(15) 0.0238(5) Uani 1 1 d . . . C24 C 0.8344(2) 1.3175(2) 0.07219(16) 0.0278(6) Uani 1 1 d . . . H24A H 0.8291 1.3255 0.0191 0.033 Uiso 1 1 calc R . . H24B H 0.9229 1.2896 0.0743 0.033 Uiso 1 1 calc R . . C25 C 0.8101(3) 1.4410(2) 0.10324(16) 0.0308(6) Uani 1 1 d . . . H25A H 0.8404 1.4386 0.1500 0.037 Uiso 1 1 calc R . . H25B H 0.8616 1.5031 0.0659 0.037 Uiso 1 1 calc R . . C26 C 0.6627(3) 1.4735(2) 0.11978(16) 0.0303(6) Uani 1 1 d . . . H26A H 0.6321 1.4735 0.0733 0.036 Uiso 1 1 calc R . . H26B H 0.6522 1.5545 0.1348 0.036 Uiso 1 1 calc R . . C27 C 0.5758(3) 1.3848(2) 0.18351(15) 0.0262(6) Uani 1 1 d . . . H27 H 0.4821 1.3950 0.1823 0.031 Uiso 1 1 calc R . . C28 C 0.6169(2) 1.2591(2) 0.16840(15) 0.0251(6) Uani 1 1 d . . . C29 C 0.6111(2) 1.0573(2) 0.18040(15) 0.0247(6) Uani 1 1 d . . . C30 C 0.5806(3) 0.9351(2) 0.20174(15) 0.0295(6) Uani 1 1 d . . . H30 H 0.5028 0.9100 0.2383 0.035 Uiso 1 1 calc R . . C31 C 0.6687(3) 0.8514(2) 0.16736(16) 0.0297(6) Uani 1 1 d . . . H31 H 0.6502 0.7691 0.1803 0.036 Uiso 1 1 calc R . . C32 C 0.5418(2) 1.4985(2) 0.29735(15) 0.0251(6) Uani 1 1 d . . . C33 C 0.5811(3) 1.5174(2) 0.36415(15) 0.0281(6) Uani 1 1 d . . . H33 H 0.6383 1.4630 0.3825 0.034 Uiso 1 1 calc R . . C34 C 0.5365(2) 1.6149(2) 0.40269(16) 0.0284(6) Uani 1 1 d . . . H34 H 0.5635 1.6258 0.4468 0.034 Uiso 1 1 calc R . . C35 C 0.4506(2) 1.6980(2) 0.37590(15) 0.0269(6) Uani 1 1 d . . . C36 C 0.4066(2) 1.6772(2) 0.31188(15) 0.0273(6) Uani 1 1 d . . . H36 H 0.3458 1.7296 0.2954 0.033 Uiso 1 1 calc R . . C37 C 0.4515(2) 1.5801(2) 0.27252(15) 0.0263(6) Uani 1 1 d . . . H37 H 0.4221 1.5685 0.2293 0.032 Uiso 1 1 calc R . . C38 C 0.4136(3) 1.8060(2) 0.41212(15) 0.0287(6) Uani 1 1 d . . . C39 C -0.1166(3) 0.1443(3) 0.42203(17) 0.0344(7) Uani 1 1 d . . . H39A H -0.0525 0.1081 0.3834 0.052 Uiso 1 1 calc R . . H39C H -0.1448 0.0863 0.4667 0.052 Uiso 1 1 calc R . . H39B H -0.0768 0.2132 0.4354 0.052 Uiso 1 1 calc R . . C40 C -0.3011(3) 0.0476(3) 0.36377(18) 0.0397(7) Uani 1 1 d . . . H40B H -0.3685 0.0580 0.3355 0.060 Uiso 1 1 calc R . . H40C H -0.3348 -0.0049 0.4104 0.060 Uiso 1 1 calc R . . H40A H -0.2236 0.0124 0.3335 0.060 Uiso 1 1 calc R . . C41 C 0.3708(3) 0.2066(3) 0.43351(18) 0.0383(7) Uani 1 1 d . . . H41B H 0.4114 0.1315 0.4464 0.058 Uiso 1 1 calc R . . H41C H 0.3382 0.2455 0.4789 0.058 Uiso 1 1 calc R . . H41A H 0.4356 0.2583 0.3970 0.058 Uiso 1 1 calc R . . C42 C 0.1974(3) 0.3319(3) 0.36749(18) 0.0404(7) Uani 1 1 d . . . H42B H 0.2761 0.3731 0.3359 0.061 Uiso 1 1 calc R . . H42C H 0.1664 0.3705 0.4131 0.061 Uiso 1 1 calc R . . H42A H 0.1291 0.3347 0.3398 0.061 Uiso 1 1 calc R . . Cl1 Cl 0.39254(6) 0.68936(6) 0.06933(4) 0.03519(18) Uani 1 1 d . . . Cl2 Cl 0.89547(7) 0.78260(6) 0.07175(4) 0.03622(18) Uani 1 1 d . . . N1 N 0.0499(2) 0.26831(18) 0.20592(12) 0.0264(5) Uani 1 1 d . . . H1 H -0.0246 0.2573 0.2400 0.032 Uiso 1 1 calc R . . N2 N 0.0998(2) -0.00085(18) 0.25834(12) 0.0272(5) Uani 1 1 d . . . H2A H 0.1451 0.0412 0.2803 0.033 Uiso 1 1 calc R . . N3 N -0.1421(2) -0.5402(2) 0.45205(15) 0.0423(6) Uani 1 1 d . . . N4 N 0.5433(2) 1.15737(18) 0.20565(12) 0.0263(5) Uani 1 1 d . . . H4 H 0.4679 1.1569 0.2390 0.032 Uiso 1 1 calc R . . N5 N 0.5903(2) 1.40203(19) 0.26016(12) 0.0277(5) Uani 1 1 d . . . H5 H 0.6320 1.3478 0.2829 0.033 Uiso 1 1 calc R . . N6 N 0.3874(2) 1.8939(2) 0.43983(13) 0.0349(6) Uani 1 1 d . . . O1 O -0.20002(18) 0.26517(17) 0.30954(11) 0.0375(5) Uani 1 1 d . . . O2 O 0.29434(17) 0.12746(17) 0.31909(11) 0.0343(4) Uani 1 1 d . . . S1 S -0.25733(6) 0.19099(6) 0.38594(4) 0.02856(17) Uani 1 1 d . . . S2 S 0.23540(6) 0.17804(6) 0.39302(4) 0.02912(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0246(15) 0.0247(14) 0.0333(16) 0.0037(11) -0.0119(11) -0.0029(10) C2 0.0201(14) 0.0262(14) 0.0281(15) 0.0008(11) -0.0076(10) 0.0006(10) C3 0.0194(14) 0.0237(14) 0.0281(14) -0.0020(11) -0.0098(10) 0.0022(10) C4 0.0202(14) 0.0252(14) 0.0286(14) -0.0039(11) -0.0106(10) 0.0012(10) C5 0.0221(14) 0.0273(14) 0.0317(15) -0.0040(11) -0.0066(10) -0.0001(10) C6 0.0258(15) 0.0258(14) 0.0377(16) -0.0051(12) -0.0062(11) 0.0014(10) C7 0.0285(15) 0.0267(14) 0.0347(16) -0.0051(12) -0.0089(11) -0.0041(11) C8 0.0199(14) 0.0247(14) 0.0311(15) -0.0012(11) -0.0099(10) -0.0034(10) C9 0.0187(14) 0.0260(14) 0.0276(14) -0.0032(11) -0.0085(10) 0.0011(10) C10 0.0203(14) 0.0263(14) 0.0282(15) -0.0012(11) -0.0067(10) 0.0001(10) C11 0.0231(15) 0.0284(15) 0.0338(16) -0.0055(12) -0.0056(11) 0.0048(10) C12 0.0271(15) 0.0219(14) 0.0396(17) -0.0046(12) -0.0120(12) 0.0029(10) C13 0.0179(13) 0.0228(14) 0.0297(15) -0.0060(11) -0.0057(10) 0.0023(10) C14 0.0222(14) 0.0274(14) 0.0301(15) -0.0020(11) -0.0111(10) -0.0005(10) C15 0.0209(14) 0.0263(14) 0.0338(16) -0.0071(12) -0.0076(11) -0.0006(10) C16 0.0242(15) 0.0241(14) 0.0306(15) -0.0012(11) -0.0067(11) -0.0001(10) C17 0.0270(15) 0.0286(15) 0.0296(15) -0.0016(12) -0.0120(11) 0.0023(11) C18 0.0213(14) 0.0278(14) 0.0332(15) -0.0042(12) -0.0105(11) -0.0006(10) C19 0.0274(16) 0.0308(16) 0.0365(16) -0.0022(13) -0.0142(12) 0.0000(11) C20 0.0268(15) 0.0280(15) 0.0334(15) -0.0105(12) -0.0136(11) 0.0036(11) C21 0.0214(14) 0.0307(15) 0.0282(15) -0.0070(11) -0.0077(10) -0.0003(10) C22 0.0194(14) 0.0291(14) 0.0302(15) -0.0059(11) -0.0111(10) -0.0004(10) C23 0.0206(14) 0.0259(14) 0.0277(14) -0.0059(11) -0.0100(10) 0.0004(10) C24 0.0194(14) 0.0300(15) 0.0331(15) -0.0045(12) -0.0048(10) 0.0033(10) C25 0.0276(15) 0.0251(14) 0.0397(17) -0.0057(12) -0.0074(12) -0.0009(11) C26 0.0296(16) 0.0262(15) 0.0350(16) -0.0045(12) -0.0077(11) 0.0029(11) C27 0.0217(14) 0.0286(14) 0.0318(15) -0.0078(11) -0.0112(10) 0.0044(10) C28 0.0232(14) 0.0265(14) 0.0280(15) -0.0051(11) -0.0101(10) 0.0002(10) C29 0.0216(14) 0.0269(14) 0.0280(15) -0.0052(11) -0.0095(10) 0.0007(10) C30 0.0242(15) 0.0321(15) 0.0324(16) -0.0044(12) -0.0069(11) -0.0029(11) C31 0.0287(16) 0.0255(14) 0.0374(16) -0.0043(12) -0.0129(12) -0.0010(11) C32 0.0204(14) 0.0228(14) 0.0321(15) -0.0037(11) -0.0061(10) -0.0023(10) C33 0.0245(15) 0.0274(14) 0.0349(16) -0.0036(12) -0.0119(11) 0.0019(10) C34 0.0250(15) 0.0300(15) 0.0328(16) -0.0058(12) -0.0109(11) -0.0018(11) C35 0.0245(15) 0.0241(14) 0.0313(15) -0.0059(11) -0.0041(11) -0.0020(10) C36 0.0214(14) 0.0270(14) 0.0326(15) -0.0014(12) -0.0061(11) 0.0019(10) C37 0.0200(14) 0.0298(15) 0.0303(15) -0.0056(11) -0.0076(10) 0.0009(10) C38 0.0231(15) 0.0314(16) 0.0306(16) -0.0024(12) -0.0055(11) -0.0004(11) C39 0.0193(15) 0.0454(18) 0.0401(17) -0.0061(13) -0.0103(11) 0.0030(12) C40 0.0310(17) 0.0451(18) 0.0462(19) -0.0087(14) -0.0135(13) -0.0053(13) C41 0.0343(17) 0.0403(17) 0.0484(19) -0.0108(14) -0.0228(13) 0.0008(12) C42 0.0309(17) 0.0396(18) 0.052(2) -0.0038(14) -0.0139(13) 0.0036(12) Cl1 0.0302(4) 0.0251(3) 0.0482(4) 0.0013(3) -0.0080(3) -0.0051(3) Cl2 0.0319(4) 0.0302(4) 0.0484(4) -0.0135(3) -0.0097(3) 0.0067(3) N1 0.0198(12) 0.0265(12) 0.0304(13) -0.0005(9) -0.0024(9) -0.0023(8) N2 0.0280(12) 0.0252(12) 0.0310(13) -0.0002(9) -0.0136(9) -0.0064(9) N3 0.0430(16) 0.0351(15) 0.0520(17) 0.0074(13) -0.0233(12) -0.0089(11) N4 0.0177(12) 0.0296(12) 0.0318(13) -0.0062(10) -0.0052(9) 0.0010(9) N5 0.0278(13) 0.0262(12) 0.0327(13) -0.0067(10) -0.0130(9) 0.0059(9) N6 0.0338(14) 0.0332(14) 0.0366(14) -0.0085(11) -0.0045(10) 0.0010(10) O1 0.0226(11) 0.0475(12) 0.0367(12) 0.0048(9) -0.0018(8) 0.0057(8) O2 0.0258(10) 0.0419(11) 0.0361(11) -0.0129(9) -0.0051(8) -0.0054(8) S1 0.0175(3) 0.0356(4) 0.0319(4) -0.0025(3) -0.0058(3) 0.0030(2) S2 0.0193(3) 0.0354(4) 0.0341(4) -0.0072(3) -0.0074(3) -0.0029(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 C1 C2 1.378(4) . y C1 C12 1.399(4) . y C1 Cl1 1.750(2) . y C2 C3 1.407(3) . y C2 H2 0.9300 . n C3 C10 1.413(3) . y C3 C4 1.431(3) . y C4 C9 1.366(3) . y C4 C5 1.503(3) . y C5 C6 1.531(4) . y C5 H5B 0.9700 . n C5 H5A 0.9700 . n C6 C7 1.527(4) . y C6 H6A 0.9700 . n C6 H6B 0.9700 . n C7 C8 1.531(4) . y C7 H7B 0.9700 . n C7 H7A 0.9700 . n C8 N2 1.466(3) . y C8 C9 1.491(3) . y C8 H8 0.9800 . n C9 N1 1.377(3) . y C10 N1 1.376(3) . y C10 C11 1.390(3) . y C11 C12 1.388(4) . y C11 H11 0.9300 . n C12 H12 0.9300 . n C13 N2 1.360(3) . y C13 C18 1.407(4) . y C13 C14 1.415(3) . y C14 C15 1.381(4) . y C14 H14 0.9300 . n C15 C16 1.393(4) . y C15 H15 0.9300 . n C16 C17 1.406(4) . y C16 C19 1.442(4) . y C17 C18 1.376(4) . y C17 H17 0.9300 . n C18 H18 0.9300 . n C19 N3 1.151(3) . y C20 C21 1.375(4) . y C20 C31 1.404(4) . y C20 Cl2 1.750(3) . y C21 C22 1.402(3) . y C21 H21 0.9300 . n C22 C29 1.422(3) . y C22 C23 1.429(4) . y C23 C28 1.363(4) . y C23 C24 1.503(3) . y C24 C25 1.541(4) . y C24 H24A 0.9700 . n C24 H24B 0.9700 . n C25 C26 1.525(4) . y C25 H25A 0.9700 . n C25 H25B 0.9700 . n C26 C27 1.537(4) . y C26 H26A 0.9700 . n C26 H26B 0.9700 . n C27 N5 1.468(3) . y C27 C28 1.493(3) . y C27 H27 0.9800 . n C28 N4 1.382(3) . y C29 N4 1.372(3) . y C29 C30 1.389(4) . y C30 C31 1.385(4) . y C30 H30 0.9300 . n C31 H31 0.9300 . n C32 N5 1.360(3) . y C32 C33 1.407(4) . y C32 C37 1.408(4) . y C33 C34 1.372(4) . y C33 H33 0.9300 . n C34 C35 1.401(4) . y C34 H34 0.9300 . n C35 C36 1.391(4) . y C35 C38 1.440(4) . y C36 C37 1.377(4) . y C36 H36 0.9300 . n C37 H37 0.9300 . n C38 N6 1.151(3) . y C39 S1 1.783(3) . y C39 H39A 0.9600 . n C39 H39C 0.9600 . n C39 H39B 0.9600 . n C40 S1 1.783(3) . y C40 H40B 0.9600 . n C40 H40C 0.9600 . n C40 H40A 0.9600 . n C41 S2 1.781(3) . y C41 H41B 0.9600 . n C41 H41C 0.9600 . n C41 H41A 0.9600 . n C42 S2 1.783(3) . y C42 H42B 0.9600 . n C42 H42C 0.9600 . n C42 H42A 0.9600 . n N1 H1 0.8600 . n N2 H2A 0.8600 . n N4 H4 0.8600 . n N5 H5 0.8600 . n O1 S1 1.5132(19) . y O2 S2 1.5002(19) . y 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 C2 C1 C12 123.1(2) . . y C2 C1 Cl1 119.0(2) . . y C12 C1 Cl1 117.9(2) . . y C1 C2 C3 117.8(2) . . y C1 C2 H2 121.1 . . n C3 C2 H2 121.1 . . n C2 C3 C10 119.0(2) . . y C2 C3 C4 133.8(2) . . y C10 C3 C4 107.2(2) . . y C9 C4 C3 106.3(2) . . y C9 C4 C5 123.0(2) . . y C3 C4 C5 130.7(2) . . y C4 C5 C6 110.1(2) . . y C4 C5 H5B 109.6 . . n C6 C5 H5B 109.6 . . n C4 C5 H5A 109.6 . . n C6 C5 H5A 109.6 . . n H5B C5 H5A 108.2 . . n C7 C6 C5 111.8(2) . . y C7 C6 H6A 109.3 . . n C5 C6 H6A 109.3 . . n C7 C6 H6B 109.3 . . n C5 C6 H6B 109.3 . . n H6A C6 H6B 107.9 . . n C6 C7 C8 112.1(2) . . y C6 C7 H7B 109.2 . . n C8 C7 H7B 109.2 . . n C6 C7 H7A 109.2 . . n C8 C7 H7A 109.2 . . n H7B C7 H7A 107.9 . . n N2 C8 C9 109.1(2) . . y N2 C8 C7 113.2(2) . . y C9 C8 C7 108.5(2) . . y N2 C8 H8 108.6 . . n C9 C8 H8 108.6 . . n C7 C8 H8 108.6 . . n C4 C9 N1 110.5(2) . . y C4 C9 C8 125.9(2) . . y N1 C9 C8 123.5(2) . . y N1 C10 C11 129.8(2) . . y N1 C10 C3 107.6(2) . . y C11 C10 C3 122.5(2) . . y C12 C11 C10 117.8(2) . . y C12 C11 H11 121.1 . . n C10 C11 H11 121.1 . . n C11 C12 C1 119.9(2) . . y C11 C12 H12 120.1 . . n C1 C12 H12 120.1 . . n N2 C13 C18 119.6(2) . . y N2 C13 C14 122.4(2) . . y C18 C13 C14 118.0(2) . . y C15 C14 C13 120.3(2) . . y C15 C14 H14 119.8 . . n C13 C14 H14 119.8 . . n C14 C15 C16 121.0(2) . . y C14 C15 H15 119.5 . . n C16 C15 H15 119.5 . . n C15 C16 C17 119.2(2) . . y C15 C16 C19 120.9(2) . . y C17 C16 C19 119.9(2) . . y C18 C17 C16 119.9(2) . . y C18 C17 H17 120.0 . . n C16 C17 H17 120.0 . . n C17 C18 C13 121.5(2) . . y C17 C18 H18 119.3 . . n C13 C18 H18 119.3 . . n N3 C19 C16 179.2(3) . . y C21 C20 C31 122.7(2) . . y C21 C20 Cl2 119.2(2) . . y C31 C20 Cl2 118.1(2) . . y C20 C21 C22 118.4(2) . . y C20 C21 H21 120.8 . . n C22 C21 H21 120.8 . . n C21 C22 C29 118.8(2) . . y C21 C22 C23 134.3(2) . . y C29 C22 C23 106.9(2) . . y C28 C23 C22 106.5(2) . . y C28 C23 C24 123.4(2) . . y C22 C23 C24 130.0(2) . . y C23 C24 C25 109.5(2) . . y C23 C24 H24A 109.8 . . n C25 C24 H24A 109.8 . . n C23 C24 H24B 109.8 . . n C25 C24 H24B 109.8 . . n H24A C24 H24B 108.2 . . n C26 C25 C24 111.4(2) . . y C26 C25 H25A 109.3 . . n C24 C25 H25A 109.3 . . n C26 C25 H25B 109.3 . . n C24 C25 H25B 109.3 . . n H25A C25 H25B 108.0 . . n C25 C26 C27 112.4(2) . . y C25 C26 H26A 109.1 . . n C27 C26 H26A 109.1 . . n C25 C26 H26B 109.1 . . n C27 C26 H26B 109.1 . . n H26A C26 H26B 107.9 . . n N5 C27 C28 108.4(2) . . y N5 C27 C26 112.8(2) . . y C28 C27 C26 108.2(2) . . y N5 C27 H27 109.1 . . n C28 C27 H27 109.1 . . n C26 C27 H27 109.1 . . n C23 C28 N4 110.6(2) . . y C23 C28 C27 126.1(2) . . y N4 C28 C27 123.3(2) . . y N4 C29 C30 130.4(2) . . y N4 C29 C22 107.7(2) . . y C30 C29 C22 121.9(2) . . y C31 C30 C29 118.5(2) . . y C31 C30 H30 120.8 . . n C29 C30 H30 120.8 . . n C30 C31 C20 119.7(2) . . y C30 C31 H31 120.2 . . n C20 C31 H31 120.2 . . n N5 C32 C33 119.2(2) . . y N5 C32 C37 122.7(2) . . y C33 C32 C37 118.1(2) . . y C34 C33 C32 121.1(2) . . y C34 C33 H33 119.4 . . n C32 C33 H33 119.4 . . n C33 C34 C35 120.3(2) . . y C33 C34 H34 119.9 . . n C35 C34 H34 119.9 . . n C36 C35 C34 118.9(2) . . y C36 C35 C38 120.7(2) . . y C34 C35 C38 120.3(2) . . y C37 C36 C35 121.1(2) . . y C37 C36 H36 119.4 . . n C35 C36 H36 119.4 . . n C36 C37 C32 120.3(2) . . y C36 C37 H37 119.8 . . n C32 C37 H37 119.8 . . n N6 C38 C35 178.0(3) . . y S1 C39 H39A 109.5 . . n S1 C39 H39C 109.5 . . n H39A C39 H39C 109.5 . . n S1 C39 H39B 109.5 . . n H39A C39 H39B 109.5 . . n H39C C39 H39B 109.5 . . n S1 C40 H40B 109.5 . . n S1 C40 H40C 109.5 . . n H40B C40 H40C 109.5 . . n S1 C40 H40A 109.5 . . n H40B C40 H40A 109.5 . . n H40C C40 H40A 109.5 . . n S2 C41 H41B 109.5 . . n S2 C41 H41C 109.5 . . n H41B C41 H41C 109.5 . . n S2 C41 H41A 109.5 . . n H41B C41 H41A 109.5 . . n H41C C41 H41A 109.5 . . n S2 C42 H42B 109.5 . . n S2 C42 H42C 109.5 . . n H42B C42 H42C 109.5 . . n S2 C42 H42A 109.5 . . n H42B C42 H42A 109.5 . . n H42C C42 H42A 109.5 . . n C10 N1 C9 108.4(2) . . y C10 N1 H1 125.8 . . n C9 N1 H1 125.8 . . n C13 N2 C8 124.7(2) . . y C13 N2 H2A 117.7 . . n C8 N2 H2A 117.7 . . n C29 N4 C28 108.3(2) . . y C29 N4 H4 125.9 . . n C28 N4 H4 125.9 . . n C32 N5 C27 123.9(2) . . y C32 N5 H5 118.0 . . n C27 N5 H5 118.0 . . n O1 S1 C39 105.25(12) . . y O1 S1 C40 105.74(13) . . y C39 S1 C40 97.94(14) . . y O2 S2 C41 106.74(13) . . y O2 S2 C42 106.19(13) . . y C41 S2 C42 97.38(14) . . y _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 64.60 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.238 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.052 _chemical_absolute_configuration rmad _database_code_depnum_ccdc_archive 'CCDC 914988' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_7982 _audit_creation_date 2012-09-11 _audit_block_code GUL-GC-702-01 _chemical_name_systematic ; Title ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N3, C2 H6 S O' _chemical_compound_source dimethylsulfoxide _chemical_formula_sum 'C22 H27 N3 O S' _chemical_formula_weight 381.52 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/n' _symmetry_space_group_name_Hall '-p 2yn' _symmetry_Int_Tables_number 14 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.059(2) _cell_length_b 7.2199(9) _cell_length_c 17.196(2) _cell_angle_alpha 90 _cell_angle_beta 99.489(2) _cell_angle_gamma 90 _cell_volume 2089.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7194 _cell_measurement_theta_min 2.4017 _cell_measurement_theta_max 29.3858 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 0.00 0.0150 1.00 0.00 0.00 0.0150 2.00 -1.00 1.00 0.1500 -2.00 1.00 -1.00 0.1500 -1.00 0.00 2.00 0.0250 1.00 0.00 -2.00 0.0250 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_F_000 816 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_absorpt_coefficient_mu 0.171 _shelx_estimated_absorpt_T_min 0.7662 _shelx_estimated_absorpt_T_max 1.0000 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.98637 _exptl_absorpt_correction_T_max 0.99836 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'Incoatec Helios mirrors' _diffrn_measurement_device_type 'Bruker-AXS Kappa Mach3 APEX-II' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 66.67 _diffrn_reflns_number 43886 _diffrn_reflns_sigmaI/netI 0.0544 _diffrn_reflns_av_R_equivalents 0.0845 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.402 _diffrn_reflns_theta_max 30.744 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 6489 _reflns_number_gt 4506 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; The reflections were merged according to the crystal class for structure refinement and the calculation of statistics. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012-4 (Sheldrick, 2012)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.7662 and 1.0000 (SADABS). Structure solution was obtained using preliminary data measured at the ANKA synchrotron facility at Karlsruhe Institute of Technology. Richard Goddard thanks Gernot Buth for assistance and advice, in particular regarding setting up and integration of data from the Stoe IPDS II instrument at the SCD beamline. The 1 0 1 reflection was shadowed by the beamstop and was not included in the refinement. Highest peak 0.55 at 0.9215 0.0959 0.0100 [ 0.83 A from H12A ] Deepest hole -0.47 at 0.3640 0.1945 -0.0015 [ 0.70 A from S1 ] ; _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^)+(0.0677P)^2^+0.7086P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 6489 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.26857(9) 0.1174(2) 0.46541(9) 0.0174(3) Uani 1 1 d D . . C2 C 0.29731(9) -0.0138(2) 0.41971(9) 0.0176(3) Uani 1 1 d D . . C3 C 0.23837(9) -0.0344(2) 0.34978(9) 0.0174(3) Uani 1 1 d D . . C4 C 0.23479(10) -0.1401(2) 0.28058(10) 0.0211(3) Uani 1 1 d D . . H4 H 0.2759 -0.2205 0.2743 0.025 Uiso 1 1 calc R . . C5 C 0.16884(10) -0.1222(2) 0.22168(10) 0.0229(3) Uani 1 1 d D . . H5 H 0.1662 -0.1909 0.1756 0.027 Uiso 1 1 calc R . . C6 C 0.10608(10) -0.0020(2) 0.23071(10) 0.0219(3) Uani 1 1 d D . . H6 H 0.0627 0.0075 0.1904 0.026 Uiso 1 1 calc R . . C7 C 0.10767(9) 0.1034(2) 0.29908(10) 0.0197(3) Uani 1 1 d D . . H7 H 0.0658 0.1814 0.3054 0.024 Uiso 1 1 calc R . . C8 C 0.17468(9) 0.0869(2) 0.35757(9) 0.0171(3) Uani 1 1 d D . . C9 C 0.37569(10) -0.1141(2) 0.43662(10) 0.0222(3) Uani 1 1 d D . . H9A H 0.3673 -0.2429 0.4214 0.027 Uiso 1 1 calc R . . H9B H 0.3948 -0.1107 0.4929 0.027 Uiso 1 1 calc R . . C10 C 0.43957(11) -0.0329(3) 0.39373(12) 0.0320(4) Uani 1 1 d D . . H10A H 0.4212 -0.0358 0.3379 0.048 Uiso 1 1 calc R . . H10B H 0.4874 -0.1048 0.4060 0.048 Uiso 1 1 calc R . . H10C H 0.4502 0.0928 0.4104 0.048 Uiso 1 1 calc R . . C11 C 0.30733(9) 0.2107(2) 0.54062(9) 0.0181(3) Uani 1 1 d D . . H11 H 0.3499 0.1300 0.5667 0.022 Uiso 1 1 calc R . . C12 C 0.34451(10) 0.3969(2) 0.52210(10) 0.0231(3) Uani 1 1 d D . . H12A H 0.3785 0.3762 0.4829 0.028 Uiso 1 1 calc R . . H12B H 0.3023 0.4804 0.4993 0.028 Uiso 1 1 calc R . . C13 C 0.39284(11) 0.4893(3) 0.59339(11) 0.0284(4) Uani 1 1 d D . . H13A H 0.3584 0.5249 0.6296 0.043 Uiso 1 1 calc R . . H13B H 0.4186 0.5972 0.5769 0.043 Uiso 1 1 calc R . . H13C H 0.4322 0.4042 0.6188 0.043 Uiso 1 1 calc R . . C14 C 0.21564(9) 0.0991(2) 0.62879(9) 0.0177(3) Uani 1 1 d D . . C15 C 0.24566(9) -0.0836(2) 0.63302(9) 0.0192(3) Uani 1 1 d D . . H15 H 0.2903 -0.1113 0.6106 0.023 Uiso 1 1 calc R . . C16 C 0.20936(9) -0.2219(2) 0.67015(9) 0.0202(3) Uani 1 1 d D . . H16 H 0.2303 -0.3412 0.6731 0.024 Uiso 1 1 calc R . . C17 C 0.14140(9) -0.1838(2) 0.70338(9) 0.0199(3) Uani 1 1 d D . . C18 C 0.11070(10) -0.0026(2) 0.69919(10) 0.0215(3) Uani 1 1 d D . . H18 H 0.0657 0.0241 0.7211 0.026 Uiso 1 1 calc R . . C19 C 0.14706(9) 0.1360(2) 0.66270(9) 0.0200(3) Uani 1 1 d D . . H19 H 0.1262 0.2553 0.6604 0.024 Uiso 1 1 calc R . . C20 C 0.10377(10) -0.3304(2) 0.74050(10) 0.0228(3) Uani 1 1 d D . . C21 C 0.05381(11) 0.8032(2) 0.48717(11) 0.0265(4) Uani 1 1 d D . . H21A H 0.0045 0.7363 0.4800 0.040 Uiso 1 1 calc R . . H21B H 0.0486 0.9097 0.4533 0.040 Uiso 1 1 calc R . . H21C H 0.0670 0.8424 0.5411 0.040 Uiso 1 1 calc R . . C22 C 0.08738(13) 0.6058(3) 0.36357(10) 0.0306(4) Uani 1 1 d D . . H22A H 0.1211 0.5214 0.3413 0.046 Uiso 1 1 calc R . . H22B H 0.0818 0.7182 0.3334 0.046 Uiso 1 1 calc R . . H22C H 0.0361 0.5505 0.3626 0.046 Uiso 1 1 calc R . . N1 N 0.19404(8) 0.17728(19) 0.42901(8) 0.0188(3) Uani 1 1 d D . . H1 H 0.1665(13) 0.260(3) 0.4485(13) 0.035(6) Uiso 1 1 d . . . N2 N 0.25144(8) 0.24372(19) 0.59555(8) 0.0188(3) Uani 1 1 d D . . H2 H 0.2197(11) 0.337(3) 0.5827(11) 0.020(5) Uiso 1 1 d . . . N3 N 0.07342(9) -0.4505(2) 0.76896(9) 0.0294(3) Uani 1 1 d D . . O1 O 0.12419(7) 0.47711(16) 0.50846(7) 0.0243(3) Uani 1 1 d D . . S1 S 0.13068(2) 0.65660(6) 0.46325(2) 0.02078(11) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0163(7) 0.0213(7) 0.0154(7) 0.0017(6) 0.0049(5) -0.0010(5) C2 0.0193(7) 0.0195(7) 0.0147(7) 0.0022(6) 0.0052(6) 0.0002(6) C3 0.0193(7) 0.0190(7) 0.0147(7) 0.0008(5) 0.0055(6) -0.0003(5) C4 0.0240(8) 0.0212(7) 0.0193(8) -0.0021(6) 0.0070(6) 0.0020(6) C5 0.0285(8) 0.0240(8) 0.0164(8) -0.0032(6) 0.0046(6) -0.0018(6) C6 0.0222(8) 0.0245(8) 0.0179(8) 0.0001(6) 0.0003(6) -0.0023(6) C7 0.0194(7) 0.0198(7) 0.0200(8) 0.0001(6) 0.0038(6) 0.0002(6) C8 0.0196(7) 0.0177(7) 0.0151(7) -0.0002(5) 0.0062(6) -0.0005(6) C9 0.0209(8) 0.0255(8) 0.0201(8) 0.0009(6) 0.0033(6) 0.0052(6) C10 0.0206(8) 0.0416(11) 0.0352(11) 0.0017(8) 0.0087(8) 0.0049(7) C11 0.0183(7) 0.0221(7) 0.0146(7) 0.0007(6) 0.0048(6) 0.0002(6) C12 0.0247(8) 0.0246(8) 0.0203(8) 0.0026(6) 0.0043(6) -0.0043(6) C13 0.0308(9) 0.0293(9) 0.0237(9) 0.0009(7) 0.0005(7) -0.0053(7) C14 0.0188(7) 0.0227(7) 0.0113(7) -0.0007(6) 0.0011(5) 0.0002(6) C15 0.0191(7) 0.0244(7) 0.0148(7) 0.0002(6) 0.0046(6) 0.0012(6) C16 0.0209(7) 0.0226(7) 0.0170(8) 0.0005(6) 0.0032(6) 0.0016(6) C17 0.0187(7) 0.0270(8) 0.0141(7) 0.0007(6) 0.0032(6) -0.0022(6) C18 0.0192(7) 0.0310(8) 0.0151(7) -0.0017(6) 0.0051(6) 0.0013(6) C19 0.0208(7) 0.0237(7) 0.0156(7) -0.0022(6) 0.0035(6) 0.0030(6) C20 0.0199(7) 0.0291(8) 0.0195(8) -0.0010(7) 0.0038(6) 0.0010(6) C21 0.0318(9) 0.0243(8) 0.0238(9) -0.0007(7) 0.0055(7) 0.0082(7) C22 0.0483(11) 0.0249(8) 0.0186(8) -0.0015(7) 0.0052(8) -0.0020(8) N1 0.0185(6) 0.0218(6) 0.0165(6) -0.0029(5) 0.0040(5) 0.0024(5) N2 0.0214(7) 0.0208(6) 0.0148(6) -0.0001(5) 0.0052(5) 0.0020(5) N3 0.0282(8) 0.0354(8) 0.0257(8) 0.0029(7) 0.0072(6) -0.0036(6) O1 0.0313(6) 0.0219(6) 0.0203(6) 0.0020(5) 0.0063(5) 0.0062(5) S1 0.0224(2) 0.02102(19) 0.0192(2) -0.00085(15) 0.00430(14) 0.00087(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(2) . y C1 N1 1.390(2) . y C1 C11 1.510(2) . y C2 C3 1.442(2) . y C2 C9 1.506(2) . y C3 C4 1.406(2) . y C3 C8 1.419(2) . y C4 C5 1.390(2) . y C5 C6 1.407(2) . y C6 C7 1.397(2) . y C7 C8 1.398(2) . y C8 N1 1.382(2) . y C9 C10 1.530(2) . y C11 N2 1.468(2) . y C11 C12 1.542(2) . y C12 C13 1.515(2) . y C14 N2 1.380(2) . y C14 C15 1.412(2) . y C14 C19 1.416(2) . y C15 C16 1.385(2) . y C16 C17 1.402(2) . y C17 C18 1.407(2) . y C17 C20 1.440(2) . y C18 C19 1.381(2) . y C20 N3 1.159(2) . y C21 S1 1.7851(18) . y C22 S1 1.7891(18) . y O1 S1 1.5246(13) . y 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 C2 C1 N1 110.09(14) . . y C2 C1 C11 130.61(14) . . y N1 C1 C11 119.06(14) . . y C1 C2 C3 106.43(14) . . y C1 C2 C9 127.67(14) . . y C3 C2 C9 125.88(14) . . y C4 C3 C8 119.18(14) . . y C4 C3 C2 133.51(15) . . y C8 C3 C2 107.28(13) . . y C5 C4 C3 118.90(15) . . y C4 C5 C6 121.07(15) . . y C7 C6 C5 121.29(15) . . y C6 C7 C8 117.35(15) . . y N1 C8 C7 130.28(15) . . y N1 C8 C3 107.51(13) . . y C7 C8 C3 122.20(14) . . y C2 C9 C10 113.77(14) . . y N2 C11 C1 112.60(13) . . y N2 C11 C12 108.91(13) . . y C1 C11 C12 110.41(13) . . y C13 C12 C11 113.84(14) . . y N2 C14 C15 123.12(15) . . y N2 C14 C19 118.70(14) . . y C15 C14 C19 118.15(15) . . y C16 C15 C14 120.74(15) . . y C15 C16 C17 120.60(15) . . y C16 C17 C18 119.18(15) . . y C16 C17 C20 119.69(15) . . y C18 C17 C20 121.12(15) . . y C19 C18 C17 120.38(15) . . y C18 C19 C14 120.95(15) . . y N3 C20 C17 178.60(19) . . y C8 N1 C1 108.67(13) . . y C14 N2 C11 121.48(13) . . y O1 S1 C21 105.58(8) . . y O1 S1 C22 105.13(8) . . y C21 S1 C22 98.01(9) . . y _refine_diff_density_max 0.550 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 915538' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment 'web_deposit_cif_file_1_JoergRust_1355386501.7993.cif' data_7993sadabs _audit_creation_date 2012-09-20 _audit_block_code GUL-GC-791-01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Title ; _chemical_melting_point ? _chemical_compound_source hexane,pentane,ethylacetate _chemical_formula_moiety 'C23 H19 N3, 0.5(C4 H8 O2)' _chemical_formula_sum 'C25 H23 N3 O' _chemical_formula_weight 381.46 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 MONOCLINIC _symmetry_space_group_name_H-M 'p 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _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 13.8860(15) _cell_length_b 9.6705(10) _cell_length_c 15.6885(16) _cell_angle_alpha 90.00 _cell_angle_beta 99.869(2) _cell_angle_gamma 90.00 _cell_volume 2075.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 9975 _cell_measurement_theta_min 2.4844 _cell_measurement_theta_max 35.4578 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 0.00 0.0530 1.00 0.00 0.00 0.0230 0.00 -1.00 1.00 0.0990 0.00 1.00 -2.00 0.1170 1.00 -2.00 -2.00 0.0800 -1.00 2.00 2.00 0.0700 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method ? _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.98700 _exptl_absorpt_correction_T_max 0.99572 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'Incoatec Helios mirrors' _diffrn_measurement_device_type 'Bruker-AXS Kappa Mach3 APEX-II' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 66.67 _diffrn_reflns_number 70526 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 34.34 _reflns_number_total 8678 _reflns_number_gt 6665 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.9437 and 1.0000 (SADABS). Highest peak 0.53 at 0.0045 0.1972 0.4174 [ 1.03 A from C1A ] Deepest hole -0.51 at 0.0402 0.3149 0.4564 [ 0.40 A from C1B ] ; _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^)+(0.0699P)^2^+0.5801P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8678 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.81577(6) 0.61834(9) 0.44945(5) 0.01508(14) Uani 1 1 d . . . C2 C 0.90727(6) 0.65774(9) 0.48898(5) 0.01668(15) Uani 1 1 d . . . C3 C 0.91169(6) 0.63378(9) 0.58002(5) 0.01725(15) Uani 1 1 d . . . C4 C 0.98593(7) 0.65059(12) 0.65224(6) 0.02413(19) Uani 1 1 d . . . H4 H 1.0474 0.6887 0.6460 0.029 Uiso 1 1 calc R . . C5 C 0.96788(8) 0.61060(12) 0.73272(6) 0.0265(2) Uani 1 1 d . . . H5 H 1.0181 0.6195 0.7818 0.032 Uiso 1 1 calc R . . C6 C 0.87655(8) 0.55709(11) 0.74297(6) 0.02352(18) Uani 1 1 d . . . H6 H 0.8663 0.5299 0.7989 0.028 Uiso 1 1 calc R . . C7 C 0.80096(7) 0.54307(10) 0.67328(5) 0.02001(16) Uani 1 1 d . . . H7 H 0.7386 0.5097 0.6806 0.024 Uiso 1 1 calc R . . C8 C 0.82037(6) 0.58012(9) 0.59158(5) 0.01599(14) Uani 1 1 d . . . C9 C 0.98931(7) 0.71131(12) 0.44786(6) 0.02509(19) Uani 1 1 d . . . H9A H 0.9742 0.6964 0.3852 0.038 Uiso 1 1 calc R . . H9B H 1.0497 0.6622 0.4716 0.038 Uiso 1 1 calc R . . H9C H 0.9979 0.8104 0.4598 0.038 Uiso 1 1 calc R . . C10 C 0.77108(6) 0.62315(9) 0.35514(5) 0.01531(14) Uani 1 1 d . . . H10 H 0.8156 0.6788 0.3248 0.018 Uiso 1 1 calc R . . C11 C 0.67241(6) 0.69696(9) 0.34241(5) 0.01691(15) Uani 1 1 d . . . C12 C 0.67115(7) 0.83898(10) 0.35706(6) 0.02257(17) Uani 1 1 d . . . H12 H 0.7312 0.8878 0.3711 0.027 Uiso 1 1 calc R . . C13 C 0.58347(9) 0.91032(13) 0.35150(8) 0.0327(2) Uani 1 1 d . . . H13 H 0.5838 1.0072 0.3616 0.039 Uiso 1 1 calc R . . C14 C 0.49526(8) 0.83978(15) 0.33116(8) 0.0367(3) Uani 1 1 d . . . H14 H 0.4351 0.8877 0.3287 0.044 Uiso 1 1 calc R . . C15 C 0.49564(8) 0.69961(15) 0.31454(8) 0.0346(3) Uani 1 1 d . . . H15 H 0.4354 0.6517 0.2993 0.041 Uiso 1 1 calc R . . C16 C 0.58395(7) 0.62741(12) 0.31994(6) 0.02526(19) Uani 1 1 d . . . H16 H 0.5835 0.5310 0.3083 0.030 Uiso 1 1 calc R . . C17 C 0.76804(6) 0.46135(9) 0.23207(5) 0.01535(14) Uani 1 1 d . . . C18 C 0.76531(8) 0.56943(9) 0.17155(5) 0.02085(17) Uani 1 1 d . . . H18 H 0.7604 0.6626 0.1896 0.025 Uiso 1 1 calc R . . C19 C 0.76971(8) 0.54047(10) 0.08566(6) 0.02220(18) Uani 1 1 d . . . H19 H 0.7688 0.6139 0.0453 0.027 Uiso 1 1 calc R . . C20 C 0.77546(7) 0.40385(9) 0.05837(5) 0.01858(16) Uani 1 1 d . . . C21 C 0.77746(7) 0.29605(9) 0.11832(5) 0.01775(15) Uani 1 1 d . . . H21 H 0.7812 0.2030 0.0998 0.021 Uiso 1 1 calc R . . C22 C 0.77401(6) 0.32382(9) 0.20366(5) 0.01639(15) Uani 1 1 d . . . H22 H 0.7757 0.2499 0.2437 0.020 Uiso 1 1 calc R . . C23 C 0.77933(8) 0.36862(10) -0.02950(6) 0.02203(18) Uani 1 1 d . . . N1 N 0.76236(6) 0.57135(8) 0.51104(4) 0.01694(14) Uani 1 1 d . . . H1 H 0.7017 0.5411 0.5004 0.020 Uiso 1 1 calc R . . N2 N 0.76511(6) 0.48500(8) 0.31783(5) 0.01910(15) Uani 1 1 d . . . H2 H 0.7594 0.4139 0.3516 0.023 Uiso 1 1 calc R . . N3 N 0.78211(8) 0.33428(10) -0.09959(5) 0.0298(2) Uani 1 1 d . . . C24 C 0.45098(17) 0.2734(3) 0.42480(18) 0.0349(5) Uani 0.50 1 d P A -2 H24A H 0.4078 0.3117 0.3744 0.052 Uiso 0.50 1 calc PR A -2 H24B H 0.4115 0.2340 0.4650 0.052 Uiso 0.50 1 calc PR A -2 H24C H 0.4919 0.2009 0.4059 0.052 Uiso 0.50 1 calc PR A -2 C25 C 0.5144(2) 0.3852(5) 0.4691(3) 0.0249(6) Uani 0.50 1 d P A -2 C26 C 0.5172(2) 0.6066(5) 0.5362(3) 0.0262(6) Uani 0.50 1 d P A -2 H26A H 0.5619 0.6461 0.4996 0.031 Uiso 0.50 1 calc PR A -2 H26B H 0.5571 0.5719 0.5903 0.031 Uiso 0.50 1 calc PR A -2 C27 C 0.44807(18) 0.7149(3) 0.55631(17) 0.0351(5) Uani 0.50 1 d P A -2 H27A H 0.4850 0.7916 0.5870 0.053 Uiso 0.50 1 calc PR A -2 H27B H 0.4045 0.6752 0.5928 0.053 Uiso 0.50 1 calc PR A -2 H27C H 0.4092 0.7492 0.5024 0.053 Uiso 0.50 1 calc PR A -2 O1 O 0.60227(11) 0.38468(16) 0.48409(11) 0.0281(3) Uani 0.50 1 d P A -2 O2 O 0.46104(10) 0.49399(16) 0.49065(9) 0.0229(3) Uani 0.50 1 d P A -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0187(3) 0.0161(3) 0.0108(3) -0.0011(2) 0.0037(2) 0.0001(3) C2 0.0180(3) 0.0205(4) 0.0118(3) -0.0005(3) 0.0034(3) 0.0010(3) C3 0.0197(4) 0.0201(4) 0.0119(3) -0.0011(3) 0.0027(3) 0.0027(3) C4 0.0213(4) 0.0361(5) 0.0142(3) -0.0026(3) 0.0008(3) 0.0038(4) C5 0.0273(4) 0.0386(6) 0.0126(3) -0.0013(3) 0.0005(3) 0.0074(4) C6 0.0345(5) 0.0246(4) 0.0121(3) 0.0006(3) 0.0058(3) 0.0057(4) C7 0.0300(4) 0.0177(4) 0.0135(3) -0.0004(3) 0.0072(3) 0.0002(3) C8 0.0221(4) 0.0143(3) 0.0118(3) -0.0014(2) 0.0035(3) 0.0011(3) C9 0.0211(4) 0.0377(5) 0.0171(4) 0.0005(4) 0.0050(3) -0.0052(4) C10 0.0195(4) 0.0154(3) 0.0110(3) -0.0020(2) 0.0027(3) -0.0008(3) C11 0.0184(4) 0.0205(4) 0.0114(3) -0.0007(3) 0.0015(3) -0.0004(3) C12 0.0221(4) 0.0214(4) 0.0238(4) -0.0021(3) 0.0028(3) 0.0033(3) C13 0.0303(5) 0.0310(5) 0.0366(6) 0.0016(4) 0.0055(4) 0.0119(4) C14 0.0221(5) 0.0516(7) 0.0360(6) 0.0127(5) 0.0034(4) 0.0126(5) C15 0.0192(4) 0.0507(7) 0.0317(5) 0.0095(5) -0.0016(4) -0.0042(4) C16 0.0218(4) 0.0305(5) 0.0217(4) 0.0019(4) -0.0011(3) -0.0061(4) C17 0.0208(4) 0.0147(3) 0.0108(3) -0.0008(2) 0.0033(3) 0.0000(3) C18 0.0366(5) 0.0137(3) 0.0125(3) -0.0006(3) 0.0047(3) 0.0001(3) C19 0.0390(5) 0.0159(4) 0.0122(3) 0.0007(3) 0.0056(3) 0.0001(3) C20 0.0295(4) 0.0158(3) 0.0111(3) -0.0007(3) 0.0053(3) 0.0011(3) C21 0.0263(4) 0.0141(3) 0.0132(3) -0.0011(3) 0.0042(3) 0.0012(3) C22 0.0227(4) 0.0145(3) 0.0122(3) 0.0000(2) 0.0037(3) 0.0006(3) C23 0.0352(5) 0.0167(4) 0.0148(3) 0.0004(3) 0.0059(3) 0.0024(3) N1 0.0193(3) 0.0203(3) 0.0117(3) -0.0016(2) 0.0040(2) -0.0032(3) N2 0.0329(4) 0.0143(3) 0.0105(3) -0.0007(2) 0.0048(3) -0.0003(3) N3 0.0498(6) 0.0248(4) 0.0162(3) -0.0020(3) 0.0096(3) 0.0033(4) C24 0.0263(10) 0.0300(11) 0.0483(13) -0.0156(10) 0.0060(9) -0.0046(8) C25 0.0223(14) 0.0270(13) 0.0259(11) 0.0002(9) 0.0056(13) -0.0019(14) C26 0.0270(16) 0.0230(11) 0.0282(12) -0.0045(8) 0.0037(14) 0.0026(15) C27 0.0322(11) 0.0320(11) 0.0424(12) -0.0081(9) 0.0102(9) 0.0069(9) O1 0.0201(6) 0.0253(7) 0.0395(8) -0.0017(6) 0.0069(6) 0.0001(5) O2 0.0185(6) 0.0247(7) 0.0260(6) -0.0042(5) 0.0053(5) 0.0006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3690(12) . y C1 N1 1.3915(11) . y C1 C10 1.5039(11) . y C2 C3 1.4379(11) . y C2 C9 1.4947(13) . y C3 C4 1.4045(12) . y C3 C8 1.4103(13) . y C4 C5 1.3838(14) . y C4 H4 0.9500 . n C5 C6 1.4043(16) . y C5 H5 0.9500 . n C6 C7 1.3864(14) . y C6 H6 0.9500 . n C7 C8 1.4008(12) . y C7 H7 0.9500 . n C8 N1 1.3798(11) . y C9 H9A 0.9800 . n C9 H9B 0.9800 . n C9 H9C 0.9800 . n C10 N2 1.4552(11) . y C10 C11 1.5274(12) . y C10 H10 1.0000 . n C11 C16 1.3917(13) . y C11 C12 1.3931(13) . y C12 C13 1.3891(14) . y C12 H12 0.9500 . n C13 C14 1.3905(18) . y C13 H13 0.9500 . n C14 C15 1.381(2) . y C14 H14 0.9500 . n C15 C16 1.4011(16) . y C15 H15 0.9500 . n C16 H16 0.9500 . n C17 N2 1.3722(10) . y C17 C18 1.4081(12) . y C17 C22 1.4097(12) . y C18 C19 1.3879(12) . y C18 H18 0.9500 . n C19 C20 1.3953(13) . y C19 H19 0.9500 . n C20 C21 1.4012(12) . y C20 C23 1.4299(12) . y C21 C22 1.3743(11) . y C21 H21 0.9500 . n C22 H22 0.9500 . n C23 N3 1.1556(12) . y N1 H1 0.8800 . n N2 H2 0.8800 . n C24 C25 1.489(5) . y C24 H24A 0.9800 . n C24 H24B 0.9800 . n C24 H24C 0.9800 . n C25 O1 1.203(3) . y C25 O2 1.362(4) . y C26 O2 1.454(4) . y C26 C27 1.491(4) . y C26 H26A 0.9900 . n C26 H26B 0.9900 . n C27 H27A 0.9800 . n C27 H27B 0.9800 . n C27 H27C 0.9800 . n 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 C2 C1 N1 109.88(7) . . y C2 C1 C10 129.17(8) . . y N1 C1 C10 120.94(8) . . y C1 C2 C3 106.46(7) . . y C1 C2 C9 128.16(8) . . y C3 C2 C9 125.35(8) . . y C4 C3 C8 119.39(8) . . y C4 C3 C2 133.09(9) . . y C8 C3 C2 107.51(7) . . y C5 C4 C3 118.75(9) . . y C5 C4 H4 120.6 . . n C3 C4 H4 120.6 . . n C4 C5 C6 121.06(9) . . y C4 C5 H5 119.5 . . n C6 C5 H5 119.5 . . n C7 C6 C5 121.48(8) . . y C7 C6 H6 119.3 . . n C5 C6 H6 119.3 . . n C6 C7 C8 117.27(9) . . y C6 C7 H7 121.4 . . n C8 C7 H7 121.4 . . n N1 C8 C7 130.43(9) . . y N1 C8 C3 107.55(7) . . y C7 C8 C3 122.01(8) . . y C2 C9 H9A 109.5 . . n C2 C9 H9B 109.5 . . n H9A C9 H9B 109.5 . . n C2 C9 H9C 109.5 . . n H9A C9 H9C 109.5 . . n H9B C9 H9C 109.5 . . n N2 C10 C1 110.66(7) . . y N2 C10 C11 112.86(7) . . y C1 C10 C11 110.65(7) . . y N2 C10 H10 107.5 . . n C1 C10 H10 107.5 . . n C11 C10 H10 107.5 . . n C16 C11 C12 118.87(9) . . y C16 C11 C10 122.70(9) . . y C12 C11 C10 118.39(8) . . y C13 C12 C11 120.99(10) . . y C13 C12 H12 119.5 . . n C11 C12 H12 119.5 . . n C12 C13 C14 119.93(11) . . y C12 C13 H13 120.0 . . n C14 C13 H13 120.0 . . n C15 C14 C13 119.56(10) . . y C15 C14 H14 120.2 . . n C13 C14 H14 120.2 . . n C14 C15 C16 120.63(11) . . y C14 C15 H15 119.7 . . n C16 C15 H15 119.7 . . n C11 C16 C15 119.99(11) . . y C11 C16 H16 120.0 . . n C15 C16 H16 120.0 . . n N2 C17 C18 122.38(8) . . y N2 C17 C22 118.72(7) . . y C18 C17 C22 118.90(7) . . y C19 C18 C17 120.29(8) . . y C19 C18 H18 119.9 . . n C17 C18 H18 119.9 . . n C18 C19 C20 120.22(8) . . y C18 C19 H19 119.9 . . n C20 C19 H19 119.9 . . n C19 C20 C21 119.61(8) . . y C19 C20 C23 122.34(8) . . y C21 C20 C23 118.05(8) . . y C22 C21 C20 120.57(8) . . y C22 C21 H21 119.7 . . n C20 C21 H21 119.7 . . n C21 C22 C17 120.41(8) . . y C21 C22 H22 119.8 . . n C17 C22 H22 119.8 . . n N3 C23 C20 177.08(10) . . y C8 N1 C1 108.60(7) . . y C8 N1 H1 125.7 . . n C1 N1 H1 125.7 . . n C17 N2 C10 122.56(7) . . y C17 N2 H2 118.7 . . n C10 N2 H2 118.7 . . n C25 C24 H24A 109.5 . . n C25 C24 H24B 109.5 . . n H24A C24 H24B 109.5 . . n C25 C24 H24C 109.5 . . n H24A C24 H24C 109.5 . . n H24B C24 H24C 109.5 . . n O1 C25 O2 122.1(4) . . y O1 C25 C24 126.0(3) . . y O2 C25 C24 111.9(2) . . y O2 C26 C27 108.6(2) . . y O2 C26 H26A 110.0 . . n C27 C26 H26A 110.0 . . n O2 C26 H26B 110.0 . . n C27 C26 H26B 110.0 . . n H26A C26 H26B 108.3 . . n C26 C27 H27A 109.5 . . n C26 C27 H27B 109.5 . . n H27A C27 H27B 109.5 . . n C26 C27 H27C 109.5 . . n H27A C27 H27C 109.5 . . n H27B C27 H27C 109.5 . . n C25 O2 C26 115.56(17) . . y _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 34.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.512 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 915539'