# Electronic Supplementary Material (ESI) for RSC Advances # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H0 N O' _chemical_formula_weight 390.31 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 9.6811(7) _cell_length_b 14.0805(11) _cell_length_c 18.2882(14) _cell_angle_alpha 67.492(4) _cell_angle_beta 88.996(4) _cell_angle_gamma 83.445(4) _cell_volume 2287.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.377 _exptl_crystal_size_mid 0.348 _exptl_crystal_size_min 0.279 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37416 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 27.58 _reflns_number_total 10498 _reflns_number_gt 4956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment . _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0089(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10498 _refine_ls_number_parameters 579 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1370 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.2011 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 O1 O 0.3328(2) 0.49106(13) 0.00489(10) 0.0793(6) Uani 1 1 d . . . N1 N 0.5800(2) 0.21192(15) 0.03629(11) 0.0537(5) Uani 1 1 d . . . H1A H 0.6569 0.1738 0.0379 0.064 Uiso 1 1 calc R . . C3 C 0.3541(2) 0.29675(17) -0.00463(12) 0.0481(6) Uani 1 1 d . . . H3A H 0.3504 0.3646 -0.0483 0.058 Uiso 1 1 calc R . . C4 C 0.3630(2) 0.44031(17) 0.14259(13) 0.0499(6) Uani 1 1 d . . . C5 C 0.4978(2) 0.19522(17) -0.08146(13) 0.0499(6) Uani 1 1 d . . . C10 C 0.4802(2) 0.22910(17) -0.01357(13) 0.0479(6) Uani 1 1 d . . . C12 C 0.3896(2) 0.30918(16) 0.07272(12) 0.0477(6) Uani 1 1 d . . . H12A H 0.3350 0.2649 0.1151 0.057 Uiso 1 1 calc R . . C14 C 0.3591(2) 0.41940(18) 0.06840(14) 0.0537(6) Uani 1 1 d . . . C19 C 0.3626(3) 0.36336(19) 0.21789(14) 0.0562(6) Uani 1 1 d . . . H19A H 0.3654 0.2946 0.2237 0.067 Uiso 1 1 calc R . . C21 C 0.2150(2) 0.2560(2) -0.00171(13) 0.0525(6) Uani 1 1 d . . . C24 C 0.5828(2) 0.19761(17) 0.17563(13) 0.0504(6) Uani 1 1 d . . . C25 C 0.5471(2) 0.26521(17) 0.09028(13) 0.0500(6) Uani 1 1 d . . . H25A H 0.6016 0.3241 0.0752 0.060 Uiso 1 1 calc R . . C28 C 0.3604(2) 0.54225(19) 0.13592(16) 0.0584(6) Uani 1 1 d . . . H28A H 0.3616 0.5950 0.0861 0.070 Uiso 1 1 calc R . . C29 C 0.6766(3) 0.2247(2) 0.21874(15) 0.0634(7) Uani 1 1 d . . . H29A H 0.7227 0.2826 0.1936 0.076 Uiso 1 1 calc R . . C31 C 0.2039(3) 0.1508(2) 0.03053(14) 0.0594(7) Uani 1 1 d . . . H31A H 0.2839 0.1039 0.0460 0.071 Uiso 1 1 calc R . . C33 C 0.3547(3) 0.4897(2) 0.27749(16) 0.0607(7) Uani 1 1 d . . . C35 C 0.3581(3) 0.3880(2) 0.28427(15) 0.0618(7) Uani 1 1 d . . . H35A H 0.3574 0.3355 0.3342 0.074 Uiso 1 1 calc R . . C37 C 0.3561(3) 0.5658(2) 0.20238(17) 0.0655(7) Uani 1 1 d . . . H37A H 0.3541 0.6345 0.1966 0.079 Uiso 1 1 calc R . . C39 C 0.6159(3) 0.1323(2) -0.08601(16) 0.0662(7) Uani 1 1 d . . . H39A H 0.6801 0.1044 -0.0438 0.079 Uiso 1 1 calc R . . C40 C 0.4024(3) 0.2332(2) -0.14417(14) 0.0649(7) Uani 1 1 d . . . H40A H 0.3215 0.2739 -0.1412 0.078 Uiso 1 1 calc R . . C42 C 0.5182(3) 0.10969(19) 0.21433(14) 0.0662(7) Uani 1 1 d . . . H42A H 0.4571 0.0890 0.1861 0.079 Uiso 1 1 calc R . . C44 C 0.6353(3) 0.0814(2) 0.33625(15) 0.0698(8) Uani 1 1 d . . . H44A H 0.6516 0.0432 0.3901 0.084 Uiso 1 1 calc R . . C46 C 0.7026(3) 0.1668(2) 0.29842(16) 0.0704(8) Uani 1 1 d . . . H46A H 0.7659 0.1860 0.3264 0.084 Uiso 1 1 calc R . . C47 C 0.6380(3) 0.1111(2) -0.15370(17) 0.0741(8) Uani 1 1 d . . . H47A H 0.7178 0.0694 -0.1569 0.089 Uiso 1 1 calc R . . C48 C 0.4253(3) 0.2116(2) -0.21112(15) 0.0736(8) Uani 1 1 d . . . H48A H 0.3605 0.2381 -0.2530 0.088 Uiso 1 1 calc R . . C49 C 0.5433(3) 0.1511(2) -0.21582(16) 0.0721(8) Uani 1 1 d . . . H49A H 0.5592 0.1371 -0.2612 0.086 Uiso 1 1 calc R . . C50 C 0.5429(3) 0.0522(2) 0.29403(15) 0.0743(8) Uani 1 1 d . . . H50A H 0.4976 -0.0061 0.3194 0.089 Uiso 1 1 calc R . . C54 C 0.3489(3) 0.5163(3) 0.35022(18) 0.0889(10) Uani 1 1 d . . . H54A H 0.3466 0.5898 0.3345 0.133 Uiso 1 1 calc R . . H54B H 0.4297 0.4821 0.3836 0.133 Uiso 1 1 calc R . . H54C H 0.2668 0.4938 0.3788 0.133 Uiso 1 1 calc R . . C55 C 0.0943(3) 0.3236(3) -0.02525(17) 0.0809(9) Uani 1 1 d . . . H55A H 0.0991 0.3946 -0.0476 0.097 Uiso 1 1 calc R . . C61 C 0.0750(3) 0.1149(3) 0.03994(18) 0.0828(9) Uani 1 1 d . . . H61A H 0.0690 0.0440 0.0615 0.099 Uiso 1 1 calc R . . C63 C -0.0443(4) 0.1833(4) 0.0176(2) 0.1005(12) Uani 1 1 d . . . H63A H -0.1310 0.1592 0.0252 0.121 Uiso 1 1 calc R . . C64 C -0.0341(4) 0.2862(4) -0.0157(2) 0.1055(13) Uani 1 1 d . . . H64A H -0.1145 0.3325 -0.0325 0.127 Uiso 1 1 calc R . . O2 O 0.8187(2) -0.00585(14) 0.51499(11) 0.0865(7) Uani 1 1 d . . . N2 N 0.9617(2) 0.23801(15) 0.54111(11) 0.0540(5) Uani 1 1 d . . . H2A H 1.0297 0.2745 0.5350 0.065 Uiso 1 1 calc R . . C7 C 0.9607(2) 0.13450(17) 0.60172(13) 0.0484(6) Uani 1 1 d . . . H7A H 1.0344 0.0884 0.5907 0.058 Uiso 1 1 calc R . . C8 C 0.8350(3) -0.00300(19) 0.58040(14) 0.0536(6) Uani 1 1 d . . . C9 C 0.8166(2) 0.09993(16) 0.59053(12) 0.0459(5) Uani 1 1 d . . . H9A H 0.7600 0.0936 0.6368 0.055 Uiso 1 1 calc R . . C11 C 0.8777(2) -0.10076(17) 0.64931(13) 0.0493(6) Uani 1 1 d . . . C13 C 0.5983(2) 0.22625(17) 0.52733(12) 0.0468(5) Uani 1 1 d . . . C16 C 0.8843(3) -0.10702(19) 0.72711(14) 0.0569(6) Uani 1 1 d . . . H16A H 0.8597 -0.0480 0.7379 0.068 Uiso 1 1 calc R . . C17 C 0.9152(3) -0.19125(19) 0.63609(15) 0.0573(6) Uani 1 1 d . . . H17A H 0.9125 -0.1892 0.5847 0.069 Uiso 1 1 calc R . . C18 C 0.9922(2) 0.13649(18) 0.68215(13) 0.0490(6) Uani 1 1 d . . . C20 C 0.8353(2) 0.37054(19) 0.43147(14) 0.0526(6) Uani 1 1 d . . . C22 C 0.8513(2) 0.26835(17) 0.49839(13) 0.0469(5) Uani 1 1 d . . . C23 C 0.7484(2) 0.19033(17) 0.51681(13) 0.0478(6) Uani 1 1 d . . . H23A H 0.7495 0.1659 0.4733 0.057 Uiso 1 1 calc R . . C26 C 0.9561(3) -0.2831(2) 0.69740(16) 0.0620(7) Uani 1 1 d . . . H26A H 0.9794 -0.3425 0.6869 0.074 Uiso 1 1 calc R . . C27 C 0.9267(3) -0.1997(2) 0.78825(14) 0.0604(7) Uani 1 1 d . . . H27A H 0.9308 -0.2019 0.8397 0.072 Uiso 1 1 calc R . . C30 C 0.7382(3) 0.3940(2) 0.37015(15) 0.0610(7) Uani 1 1 d . . . H30A H 0.6748 0.3478 0.3733 0.073 Uiso 1 1 calc R . . C32 C 0.9636(2) -0.28961(19) 0.77491(15) 0.0587(6) Uani 1 1 d . . . C34 C 0.4915(3) 0.1771(2) 0.51292(15) 0.0631(7) Uani 1 1 d . . . H34A H 0.5120 0.1251 0.4935 0.076 Uiso 1 1 calc R . . C36 C 0.5630(3) 0.3043(2) 0.55460(14) 0.0601(7) Uani 1 1 d . . . H36A H 0.6326 0.3385 0.5646 0.072 Uiso 1 1 calc R . . C38 C 0.9171(3) 0.2065(2) 0.70768(15) 0.0657(7) Uani 1 1 d . . . H38A H 0.8431 0.2505 0.6765 0.079 Uiso 1 1 calc R . . C41 C 0.3217(3) 0.2822(2) 0.55399(16) 0.0729(8) Uani 1 1 d . . . H41A H 0.2296 0.3007 0.5631 0.087 Uiso 1 1 calc R . . C43 C 0.9250(3) 0.4423(2) 0.42668(16) 0.0677(7) Uani 1 1 d . . . H43A H 0.9889 0.4289 0.4678 0.081 Uiso 1 1 calc R . . C45 C 0.4257(3) 0.3327(2) 0.56747(16) 0.0728(8) Uani 1 1 d . . . H45A H 0.4040 0.3861 0.5853 0.087 Uiso 1 1 calc R . . C51 C 1.0990(3) 0.0715(2) 0.73084(16) 0.0737(8) Uani 1 1 d . . . H51A H 1.1504 0.0226 0.7155 0.088 Uiso 1 1 calc R . . C52 C 0.3546(3) 0.2049(2) 0.52718(17) 0.0764(8) Uani 1 1 d . . . H52A H 0.2845 0.1703 0.5183 0.092 Uiso 1 1 calc R . . C53 C 0.7355(3) 0.4856(2) 0.30457(17) 0.0741(8) Uani 1 1 d . . . H53A H 0.6713 0.5004 0.2633 0.089 Uiso 1 1 calc R . . C56 C 0.8279(3) 0.5549(2) 0.30034(19) 0.0835(9) Uani 1 1 d . . . H56A H 0.8272 0.6160 0.2559 0.100 Uiso 1 1 calc R . . C57 C 0.9202(3) 0.5336(2) 0.36133(19) 0.0837(9) Uani 1 1 d . . . H57A H 0.9809 0.5813 0.3588 0.100 Uiso 1 1 calc R . . C58 C 1.0097(3) -0.3914(2) 0.84157(17) 0.0834(9) Uani 1 1 d . . . H58A H 1.0092 -0.3817 0.8907 0.125 Uiso 1 1 calc R . . H58B H 1.1020 -0.4167 0.8323 0.125 Uiso 1 1 calc R . . H58C H 0.9471 -0.4407 0.8440 0.125 Uiso 1 1 calc R . . C59 C 1.1318(4) 0.0775(3) 0.80238(18) 0.0912(10) Uani 1 1 d . . . H59A H 1.2045 0.0330 0.8345 0.109 Uiso 1 1 calc R . . C60 C 0.9502(4) 0.2125(3) 0.77954(18) 0.0823(9) Uani 1 1 d . . . H60A H 0.8987 0.2604 0.7959 0.099 Uiso 1 1 calc R . . C62 C 1.0574(4) 0.1486(3) 0.82552(18) 0.0885(10) Uani 1 1 d . . . H62A H 1.0803 0.1533 0.8731 0.106 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1244(17) 0.0501(10) 0.0526(11) -0.0090(9) -0.0094(11) -0.0037(10) N1 0.0451(12) 0.0605(12) 0.0514(11) -0.0179(10) 0.0009(9) -0.0026(9) C3 0.0516(15) 0.0483(13) 0.0389(12) -0.0104(10) -0.0014(10) -0.0059(11) C4 0.0480(14) 0.0461(13) 0.0542(14) -0.0167(11) -0.0010(11) -0.0084(11) C5 0.0505(15) 0.0514(14) 0.0453(13) -0.0146(11) 0.0051(11) -0.0107(11) C10 0.0471(14) 0.0500(13) 0.0416(12) -0.0107(10) 0.0004(10) -0.0108(11) C12 0.0540(15) 0.0439(12) 0.0410(12) -0.0110(10) 0.0002(10) -0.0084(11) C14 0.0556(16) 0.0484(14) 0.0525(15) -0.0140(12) 0.0026(12) -0.0078(11) C19 0.0616(16) 0.0523(14) 0.0572(15) -0.0230(12) 0.0025(12) -0.0092(12) C21 0.0482(15) 0.0672(17) 0.0411(12) -0.0215(12) -0.0042(10) 0.0001(12) C24 0.0551(15) 0.0483(14) 0.0463(13) -0.0163(11) -0.0065(11) -0.0049(11) C25 0.0538(15) 0.0470(13) 0.0477(13) -0.0145(11) -0.0004(11) -0.0135(11) C28 0.0546(16) 0.0520(15) 0.0665(16) -0.0198(12) 0.0039(12) -0.0080(12) C29 0.0605(17) 0.0727(17) 0.0620(16) -0.0290(14) -0.0086(13) -0.0138(13) C31 0.0550(17) 0.0736(18) 0.0545(15) -0.0276(13) 0.0020(12) -0.0159(13) C33 0.0520(16) 0.0705(18) 0.0692(17) -0.0373(15) 0.0005(13) -0.0074(13) C35 0.0655(18) 0.0635(17) 0.0568(15) -0.0227(13) 0.0027(13) -0.0102(13) C37 0.0674(18) 0.0551(16) 0.0800(19) -0.0320(15) 0.0011(14) -0.0094(13) C39 0.0673(18) 0.0639(16) 0.0644(17) -0.0230(14) -0.0008(13) -0.0009(14) C40 0.0575(17) 0.0823(19) 0.0524(15) -0.0248(14) 0.0011(12) -0.0014(14) C42 0.085(2) 0.0558(16) 0.0524(15) -0.0129(12) -0.0175(14) -0.0138(14) C44 0.082(2) 0.0759(19) 0.0467(14) -0.0214(14) -0.0156(14) 0.0060(16) C46 0.0699(19) 0.088(2) 0.0614(17) -0.0380(16) -0.0174(14) -0.0043(16) C47 0.083(2) 0.0670(18) 0.0716(18) -0.0299(15) 0.0068(16) 0.0036(15) C48 0.076(2) 0.093(2) 0.0530(16) -0.0307(15) -0.0008(14) -0.0065(17) C49 0.095(2) 0.0688(18) 0.0583(16) -0.0297(14) 0.0127(16) -0.0163(17) C50 0.092(2) 0.0614(17) 0.0575(16) -0.0073(13) -0.0079(15) -0.0173(15) C54 0.094(2) 0.108(2) 0.086(2) -0.061(2) 0.0050(18) -0.0091(19) C55 0.061(2) 0.097(2) 0.0772(19) -0.0292(17) -0.0168(15) 0.0124(17) C61 0.073(2) 0.119(3) 0.0743(19) -0.0496(19) 0.0137(16) -0.041(2) C63 0.054(2) 0.183(4) 0.090(3) -0.076(3) 0.0015(18) -0.031(3) C64 0.054(2) 0.159(4) 0.101(3) -0.055(3) -0.0239(19) 0.023(2) O2 0.1367(19) 0.0687(12) 0.0596(11) -0.0348(10) -0.0283(11) 0.0076(12) N2 0.0474(12) 0.0638(13) 0.0533(12) -0.0221(10) 0.0060(10) -0.0182(10) C7 0.0457(14) 0.0532(14) 0.0483(13) -0.0224(11) 0.0029(10) -0.0031(11) C8 0.0566(15) 0.0592(15) 0.0503(14) -0.0265(12) -0.0031(11) -0.0074(12) C9 0.0490(14) 0.0492(13) 0.0410(12) -0.0186(10) 0.0017(10) -0.0068(10) C11 0.0460(14) 0.0520(14) 0.0515(13) -0.0212(11) 0.0013(11) -0.0073(11) C13 0.0430(14) 0.0555(14) 0.0413(12) -0.0167(11) -0.0010(10) -0.0088(11) C16 0.0610(16) 0.0587(15) 0.0534(14) -0.0245(12) 0.0029(12) -0.0060(12) C17 0.0614(16) 0.0606(16) 0.0548(14) -0.0281(13) 0.0045(12) -0.0053(12) C18 0.0489(14) 0.0541(14) 0.0465(13) -0.0203(11) 0.0000(11) -0.0118(11) C20 0.0495(15) 0.0585(15) 0.0507(14) -0.0220(12) 0.0082(11) -0.0066(12) C22 0.0414(14) 0.0566(14) 0.0459(12) -0.0235(11) 0.0045(10) -0.0054(11) C23 0.0494(14) 0.0541(14) 0.0445(12) -0.0238(11) 0.0011(10) -0.0074(11) C26 0.0594(17) 0.0586(16) 0.0714(18) -0.0293(14) 0.0126(13) -0.0062(13) C27 0.0652(17) 0.0637(17) 0.0474(14) -0.0168(13) 0.0022(12) -0.0046(13) C30 0.0496(15) 0.0681(17) 0.0599(16) -0.0200(14) 0.0013(12) -0.0011(12) C32 0.0501(15) 0.0562(15) 0.0619(16) -0.0144(13) 0.0062(12) -0.0049(12) C34 0.0562(17) 0.0652(16) 0.0690(17) -0.0250(14) -0.0066(13) -0.0130(13) C36 0.0437(15) 0.0814(18) 0.0665(16) -0.0405(15) 0.0034(12) -0.0095(13) C38 0.0699(18) 0.0697(17) 0.0630(16) -0.0322(14) -0.0020(13) -0.0058(14) C41 0.0426(16) 0.088(2) 0.0734(19) -0.0163(16) 0.0031(13) -0.0022(15) C43 0.0655(18) 0.0635(17) 0.0701(18) -0.0193(14) -0.0025(14) -0.0134(14) C45 0.0566(18) 0.091(2) 0.0746(19) -0.0389(17) 0.0055(14) 0.0011(16) C51 0.0642(18) 0.086(2) 0.0715(18) -0.0321(16) -0.0125(14) 0.0001(15) C52 0.0509(18) 0.084(2) 0.084(2) -0.0170(17) -0.0081(15) -0.0228(15) C53 0.0573(18) 0.0774(19) 0.0663(18) -0.0078(15) -0.0034(14) 0.0063(16) C56 0.072(2) 0.0641(19) 0.087(2) -0.0014(16) 0.0084(17) -0.0001(17) C57 0.081(2) 0.0635(18) 0.092(2) -0.0104(17) 0.0009(18) -0.0185(16) C58 0.084(2) 0.0692(19) 0.077(2) -0.0089(15) 0.0037(16) 0.0030(16) C59 0.083(2) 0.119(3) 0.069(2) -0.030(2) -0.0262(17) -0.014(2) C60 0.090(2) 0.104(2) 0.075(2) -0.0555(19) 0.0142(18) -0.024(2) C62 0.097(3) 0.121(3) 0.0616(19) -0.042(2) 0.0035(18) -0.044(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 O1 C14 1.219(3) . ? N1 C10 1.278(3) . ? N1 C25 1.463(3) . ? N1 H1A 0.8600 . ? C3 C10 1.507(3) . ? C3 C21 1.516(3) . ? C3 C12 1.540(3) . ? C3 H3A 0.9800 . ? C4 C19 1.389(3) . ? C4 C28 1.390(3) . ? C4 C14 1.496(3) . ? C5 C40 1.382(3) . ? C5 C39 1.385(3) . ? C5 C10 1.492(3) . ? C12 C14 1.518(3) . ? C12 C25 1.569(3) . ? C12 H12A 0.9800 . ? C19 C35 1.383(3) . ? C19 H19A 0.9300 . ? C21 C55 1.381(3) . ? C21 C31 1.384(3) . ? C24 C42 1.384(3) . ? C24 C29 1.387(3) . ? C24 C25 1.506(3) . ? C25 H25A 0.9800 . ? C28 C37 1.376(3) . ? C28 H28A 0.9300 . ? C29 C46 1.381(4) . ? C29 H29A 0.9300 . ? C31 C61 1.383(4) . ? C31 H31A 0.9300 . ? C33 C37 1.382(4) . ? C33 C35 1.386(3) . ? C33 C54 1.512(3) . ? C35 H35A 0.9300 . ? C37 H37A 0.9300 . ? C39 C47 1.388(3) . ? C39 H39A 0.9300 . ? C40 C48 1.379(3) . ? C40 H40A 0.9300 . ? C42 C50 1.379(3) . ? C42 H42A 0.9300 . ? C44 C46 1.369(4) . ? C44 C50 1.385(4) . ? C44 H44A 0.9300 . ? C46 H46A 0.9300 . ? C47 C49 1.370(4) . ? C47 H47A 0.9300 . ? C48 C49 1.366(4) . ? C48 H48A 0.9300 . ? C49 H49A 0.9300 . ? C50 H50A 0.9300 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C55 C64 1.387(5) . ? C55 H55A 0.9300 . ? C61 C63 1.375(5) . ? C61 H61A 0.9300 . ? C63 C64 1.354(5) . ? C63 H63A 0.9300 . ? C64 H64A 0.9300 . ? O2 C8 1.226(3) . ? N2 C22 1.267(3) . ? N2 C7 1.456(3) . ? N2 H2A 0.8600 . ? C7 C18 1.519(3) . ? C7 C9 1.571(3) . ? C7 H7A 0.9800 . ? C8 C11 1.488(3) . ? C8 C9 1.521(3) . ? C9 C23 1.549(3) . ? C9 H9A 0.9800 . ? C11 C17 1.393(3) . ? C11 C16 1.394(3) . ? C13 C36 1.379(3) . ? C13 C34 1.389(3) . ? C13 C23 1.517(3) . ? C16 C27 1.378(3) . ? C16 H16A 0.9300 . ? C17 C26 1.370(3) . ? C17 H17A 0.9300 . ? C18 C51 1.376(3) . ? C18 C38 1.377(3) . ? C20 C43 1.383(3) . ? C20 C30 1.390(3) . ? C20 C22 1.483(3) . ? C22 C23 1.506(3) . ? C23 H23A 0.9800 . ? C26 C32 1.388(3) . ? C26 H26A 0.9300 . ? C27 C32 1.386(3) . ? C27 H27A 0.9300 . ? C30 C53 1.383(4) . ? C30 H30A 0.9300 . ? C32 C58 1.509(3) . ? C34 C52 1.388(4) . ? C34 H34A 0.9300 . ? C36 C45 1.386(3) . ? C36 H36A 0.9300 . ? C38 C60 1.394(3) . ? C38 H38A 0.9300 . ? C41 C52 1.360(4) . ? C41 C45 1.373(4) . ? C41 H41A 0.9300 . ? C43 C57 1.376(4) . ? C43 H43A 0.9300 . ? C45 H45A 0.9300 . ? C51 C59 1.387(4) . ? C51 H51A 0.9300 . ? C52 H52A 0.9300 . ? C53 C56 1.378(4) . ? C53 H53A 0.9300 . ? C56 C57 1.360(4) . ? C56 H56A 0.9300 . ? C57 H57A 0.9300 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 C62 1.359(5) . ? C59 H59A 0.9300 . ? C60 C62 1.353(4) . ? C60 H60A 0.9300 . ? C62 H62A 0.9300 . ? 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 C10 N1 C25 111.46(19) . . ? C10 N1 H1A 124.3 . . ? C25 N1 H1A 124.3 . . ? C10 C3 C21 116.46(19) . . ? C10 C3 C12 102.16(17) . . ? C21 C3 C12 112.11(18) . . ? C10 C3 H3A 108.6 . . ? C21 C3 H3A 108.6 . . ? C12 C3 H3A 108.6 . . ? C19 C4 C28 118.3(2) . . ? C19 C4 C14 123.2(2) . . ? C28 C4 C14 118.5(2) . . ? C40 C5 C39 118.7(2) . . ? C40 C5 C10 120.4(2) . . ? C39 C5 C10 120.6(2) . . ? N1 C10 C5 120.9(2) . . ? N1 C10 C3 115.27(19) . . ? C5 C10 C3 123.37(19) . . ? C14 C12 C3 113.73(18) . . ? C14 C12 C25 113.24(18) . . ? C3 C12 C25 104.45(17) . . ? C14 C12 H12A 108.4 . . ? C3 C12 H12A 108.4 . . ? C25 C12 H12A 108.4 . . ? O1 C14 C4 119.8(2) . . ? O1 C14 C12 120.5(2) . . ? C4 C14 C12 119.7(2) . . ? C35 C19 C4 120.7(2) . . ? C35 C19 H19A 119.7 . . ? C4 C19 H19A 119.7 . . ? C55 C21 C31 118.3(3) . . ? C55 C21 C3 120.3(2) . . ? C31 C21 C3 121.2(2) . . ? C42 C24 C29 118.1(2) . . ? C42 C24 C25 121.1(2) . . ? C29 C24 C25 120.8(2) . . ? N1 C25 C24 113.17(18) . . ? N1 C25 C12 105.10(16) . . ? C24 C25 C12 114.63(19) . . ? N1 C25 H25A 107.9 . . ? C24 C25 H25A 107.9 . . ? C12 C25 H25A 107.9 . . ? C37 C28 C4 120.6(2) . . ? C37 C28 H28A 119.7 . . ? C4 C28 H28A 119.7 . . ? C46 C29 C24 121.0(3) . . ? C46 C29 H29A 119.5 . . ? C24 C29 H29A 119.5 . . ? C61 C31 C21 120.7(3) . . ? C61 C31 H31A 119.7 . . ? C21 C31 H31A 119.7 . . ? C37 C33 C35 118.0(2) . . ? C37 C33 C54 121.2(2) . . ? C35 C33 C54 120.8(3) . . ? C19 C35 C33 121.0(2) . . ? C19 C35 H35A 119.5 . . ? C33 C35 H35A 119.5 . . ? C28 C37 C33 121.5(2) . . ? C28 C37 H37A 119.2 . . ? C33 C37 H37A 119.2 . . ? C5 C39 C47 119.8(2) . . ? C5 C39 H39A 120.1 . . ? C47 C39 H39A 120.1 . . ? C48 C40 C5 121.0(2) . . ? C48 C40 H40A 119.5 . . ? C5 C40 H40A 119.5 . . ? C50 C42 C24 121.1(2) . . ? C50 C42 H42A 119.5 . . ? C24 C42 H42A 119.5 . . ? C46 C44 C50 119.8(2) . . ? C46 C44 H44A 120.1 . . ? C50 C44 H44A 120.1 . . ? C44 C46 C29 120.1(2) . . ? C44 C46 H46A 119.9 . . ? C29 C46 H46A 119.9 . . ? C49 C47 C39 120.5(3) . . ? C49 C47 H47A 119.8 . . ? C39 C47 H47A 119.8 . . ? C49 C48 C40 120.0(3) . . ? C49 C48 H48A 120.0 . . ? C40 C48 H48A 120.0 . . ? C48 C49 C47 120.0(3) . . ? C48 C49 H49A 120.0 . . ? C47 C49 H49A 120.0 . . ? C42 C50 C44 119.9(3) . . ? C42 C50 H50A 120.1 . . ? C44 C50 H50A 120.1 . . ? C33 C54 H54A 109.5 . . ? C33 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C33 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C21 C55 C64 120.3(3) . . ? C21 C55 H55A 119.9 . . ? C64 C55 H55A 119.9 . . ? C63 C61 C31 120.3(3) . . ? C63 C61 H61A 119.8 . . ? C31 C61 H61A 119.8 . . ? C64 C63 C61 119.3(3) . . ? C64 C63 H63A 120.3 . . ? C61 C63 H63A 120.3 . . ? C63 C64 C55 121.1(3) . . ? C63 C64 H64A 119.5 . . ? C55 C64 H64A 119.5 . . ? C22 N2 C7 112.44(19) . . ? C22 N2 H2A 123.8 . . ? C7 N2 H2A 123.8 . . ? N2 C7 C18 109.36(17) . . ? N2 C7 C9 105.46(17) . . ? C18 C7 C9 116.76(18) . . ? N2 C7 H7A 108.3 . . ? C18 C7 H7A 108.3 . . ? C9 C7 H7A 108.3 . . ? O2 C8 C11 119.4(2) . . ? O2 C8 C9 120.3(2) . . ? C11 C8 C9 120.26(19) . . ? C8 C9 C23 113.05(17) . . ? C8 C9 C7 111.28(18) . . ? C23 C9 C7 104.24(17) . . ? C8 C9 H9A 109.4 . . ? C23 C9 H9A 109.4 . . ? C7 C9 H9A 109.4 . . ? C17 C11 C16 117.6(2) . . ? C17 C11 C8 118.9(2) . . ? C16 C11 C8 123.5(2) . . ? C36 C13 C34 117.7(2) . . ? C36 C13 C23 122.1(2) . . ? C34 C13 C23 120.1(2) . . ? C27 C16 C11 120.7(2) . . ? C27 C16 H16A 119.6 . . ? C11 C16 H16A 119.6 . . ? C26 C17 C11 121.2(2) . . ? C26 C17 H17A 119.4 . . ? C11 C17 H17A 119.4 . . ? C51 C18 C38 117.5(2) . . ? C51 C18 C7 121.7(2) . . ? C38 C18 C7 120.8(2) . . ? C43 C20 C30 118.6(2) . . ? C43 C20 C22 119.6(2) . . ? C30 C20 C22 121.7(2) . . ? N2 C22 C20 120.3(2) . . ? N2 C22 C23 115.1(2) . . ? C20 C22 C23 124.43(19) . . ? C22 C23 C13 117.47(18) . . ? C22 C23 C9 102.53(17) . . ? C13 C23 C9 114.10(18) . . ? C22 C23 H23A 107.4 . . ? C13 C23 H23A 107.4 . . ? C9 C23 H23A 107.4 . . ? C17 C26 C32 121.4(2) . . ? C17 C26 H26A 119.3 . . ? C32 C26 H26A 119.3 . . ? C16 C27 C32 121.5(2) . . ? C16 C27 H27A 119.2 . . ? C32 C27 H27A 119.2 . . ? C53 C30 C20 120.4(3) . . ? C53 C30 H30A 119.8 . . ? C20 C30 H30A 119.8 . . ? C27 C32 C26 117.5(2) . . ? C27 C32 C58 121.8(2) . . ? C26 C32 C58 120.6(2) . . ? C52 C34 C13 120.7(2) . . ? C52 C34 H34A 119.7 . . ? C13 C34 H34A 119.7 . . ? C13 C36 C45 121.2(2) . . ? C13 C36 H36A 119.4 . . ? C45 C36 H36A 119.4 . . ? C18 C38 C60 121.0(3) . . ? C18 C38 H38A 119.5 . . ? C60 C38 H38A 119.5 . . ? C52 C41 C45 119.3(3) . . ? C52 C41 H41A 120.3 . . ? C45 C41 H41A 120.3 . . ? C57 C43 C20 120.3(3) . . ? C57 C43 H43A 119.8 . . ? C20 C43 H43A 119.8 . . ? C41 C45 C36 120.2(3) . . ? C41 C45 H45A 119.9 . . ? C36 C45 H45A 119.9 . . ? C18 C51 C59 121.3(3) . . ? C18 C51 H51A 119.3 . . ? C59 C51 H51A 119.3 . . ? C41 C52 C34 120.8(3) . . ? C41 C52 H52A 119.6 . . ? C34 C52 H52A 119.6 . . ? C56 C53 C30 120.0(3) . . ? C56 C53 H53A 120.0 . . ? C30 C53 H53A 120.0 . . ? C57 C56 C53 119.8(3) . . ? C57 C56 H56A 120.1 . . ? C53 C56 H56A 120.1 . . ? C56 C57 C43 120.9(3) . . ? C56 C57 H57A 119.5 . . ? C43 C57 H57A 119.5 . . ? C32 C58 H58A 109.5 . . ? C32 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C32 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C62 C59 C51 119.9(3) . . ? C62 C59 H59A 120.1 . . ? C51 C59 H59A 120.1 . . ? C62 C60 C38 120.0(3) . . ? C62 C60 H60A 120.0 . . ? C38 C60 H60A 120.0 . . ? C60 C62 C59 120.2(3) . . ? C60 C62 H62A 119.9 . . ? C59 C62 H62A 119.9 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.198 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 942210' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 N0.33 O0.33' _chemical_formula_sum 'C8 H7 N0.33 O0.33' _chemical_formula_weight 113.14 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 P2(1)/n loop_ _symmetry_equiv_pos_as_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 8.7440(2) _cell_length_b 16.3482(3) _cell_length_c 13.1750(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.6940(10) _cell_angle_gamma 90.00 _cell_volume 1870.51(7) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29598 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4285 _reflns_number_gt 2961 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.2299P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment . _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0082(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4285 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 N1 N 0.93994(13) 0.14642(7) 0.54142(9) 0.0546(3) Uani 1 1 d . . . C9 C 1.02204(13) 0.28485(8) 0.55669(10) 0.0467(3) Uani 1 1 d . . . H9A H 1.0118 0.3172 0.4937 0.056 Uiso 1 1 calc R . . C13 C 1.14414(14) 0.32393(8) 0.63279(10) 0.0483(3) Uani 1 1 d . . . C10 C 1.04925(14) 0.19604(8) 0.52981(9) 0.0476(3) Uani 1 1 d . . . C8 C 0.86364(14) 0.28062(8) 0.59724(11) 0.0520(3) Uani 1 1 d . . . H8A H 0.8771 0.2913 0.6709 0.062 Uiso 1 1 calc R . . C19 C 1.18829(14) 0.16824(8) 0.48532(10) 0.0501(3) Uani 1 1 d . . . C7 C 0.81031(15) 0.18948(8) 0.57825(11) 0.0530(3) Uani 1 1 d . . . H7A H 0.7244 0.1892 0.5234 0.064 Uiso 1 1 calc R . . C20 C 1.28582(16) 0.22377(10) 0.44611(11) 0.0595(4) Uani 1 1 d . . . H20A H 1.2673 0.2795 0.4513 0.071 Uiso 1 1 calc R . . C6 C 0.75762(17) 0.14734(8) 0.66994(12) 0.0575(4) Uani 1 1 d . . . C18 C 1.22432(16) 0.27874(10) 0.71043(11) 0.0609(4) Uani 1 1 d . . . H18A H 1.2085 0.2226 0.7134 0.073 Uiso 1 1 calc R . . C24 C 1.21915(17) 0.08530(10) 0.47745(13) 0.0675(4) Uani 1 1 d . . . H24A H 1.1560 0.0470 0.5040 0.081 Uiso 1 1 calc R . . C14 C 1.17134(16) 0.40715(9) 0.62984(12) 0.0617(4) Uani 1 1 d . . . H14A H 1.1194 0.4386 0.5780 0.074 Uiso 1 1 calc R . . C11 C 0.74655(17) 0.33977(10) 0.54602(17) 0.0729(5) Uani 1 1 d . . . C21 C 1.41084(17) 0.19705(11) 0.39917(12) 0.0694(4) Uani 1 1 d . . . H21A H 1.4753 0.2349 0.3731 0.083 Uiso 1 1 calc R . . C5 C 0.6024(2) 0.14135(10) 0.68166(15) 0.0740(5) Uani 1 1 d . . . H5A H 0.5296 0.1645 0.6330 0.089 Uiso 1 1 calc R . . C22 C 1.43941(19) 0.11556(12) 0.39122(14) 0.0786(5) Uani 1 1 d . . . H22A H 1.5231 0.0978 0.3596 0.094 Uiso 1 1 calc R . . C23 C 1.3442(2) 0.05972(11) 0.43003(15) 0.0827(5) Uani 1 1 d . . . H23A H 1.3639 0.0041 0.4244 0.099 Uiso 1 1 calc R . . C17 C 1.32713(19) 0.31583(12) 0.78332(13) 0.0736(5) Uani 1 1 d . . . H17A H 1.3800 0.2845 0.8349 0.088 Uiso 1 1 calc R . . C16 C 1.35217(19) 0.39841(13) 0.78050(14) 0.0792(5) Uani 1 1 d . . . H16A H 1.4208 0.4232 0.8304 0.095 Uiso 1 1 calc R . . C15 C 1.27514(19) 0.44441(11) 0.70332(15) 0.0767(5) Uani 1 1 d . . . H15A H 1.2926 0.5004 0.7004 0.092 Uiso 1 1 calc R . . C1 C 0.8633(2) 0.11263(10) 0.74334(13) 0.0747(5) Uani 1 1 d . . . H1B H 0.9679 0.1164 0.7370 0.090 Uiso 1 1 calc R . . C12 C 0.6093(2) 0.35663(12) 0.6004(2) 0.1091(8) Uani 1 1 d . . . H12A H 0.5426 0.3945 0.5611 0.164 Uiso 1 1 calc R . . H12B H 0.6423 0.3797 0.6663 0.164 Uiso 1 1 calc R . . H12C H 0.5549 0.3065 0.6086 0.164 Uiso 1 1 calc R . . O1 O 0.76116(17) 0.37115(11) 0.46563(15) 0.1294(7) Uani 1 1 d . . . C4 C 0.5549(3) 0.10158(13) 0.7644(2) 0.0998(7) Uani 1 1 d . . . H4A H 0.4506 0.0987 0.7719 0.120 Uiso 1 1 calc R . . C2 C 0.8151(3) 0.07230(12) 0.82631(16) 0.0983(7) Uani 1 1 d . . . H2A H 0.8871 0.0493 0.8756 0.118 Uiso 1 1 calc R . . C3 C 0.6601(4) 0.06637(12) 0.83569(18) 0.1064(8) Uani 1 1 d . . . H3A H 0.6273 0.0383 0.8906 0.128 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 N1 0.0528(6) 0.0527(7) 0.0596(7) -0.0071(5) 0.0120(5) -0.0014(5) C9 0.0420(6) 0.0480(7) 0.0505(7) 0.0005(5) 0.0078(5) 0.0022(5) C13 0.0417(6) 0.0520(8) 0.0527(7) -0.0042(6) 0.0120(5) 0.0012(6) C10 0.0454(7) 0.0506(7) 0.0469(7) -0.0028(5) 0.0055(5) 0.0027(6) C8 0.0449(7) 0.0533(8) 0.0594(8) -0.0036(6) 0.0120(6) 0.0017(6) C19 0.0451(7) 0.0547(8) 0.0498(7) -0.0064(6) 0.0030(5) 0.0054(6) C7 0.0443(7) 0.0548(8) 0.0605(8) -0.0039(6) 0.0087(6) -0.0016(6) C20 0.0554(8) 0.0621(9) 0.0628(9) 0.0015(7) 0.0146(6) 0.0078(7) C6 0.0614(9) 0.0459(8) 0.0678(9) -0.0056(6) 0.0187(7) -0.0054(6) C18 0.0590(8) 0.0649(9) 0.0582(8) -0.0002(7) 0.0037(7) 0.0012(7) C24 0.0559(8) 0.0586(9) 0.0884(11) -0.0147(8) 0.0101(8) 0.0021(7) C14 0.0548(8) 0.0556(9) 0.0748(10) -0.0055(7) 0.0087(7) 0.0019(7) C11 0.0482(8) 0.0583(9) 0.1131(14) 0.0047(9) 0.0129(9) 0.0071(7) C21 0.0582(9) 0.0859(12) 0.0670(9) -0.0010(8) 0.0200(7) 0.0071(8) C5 0.0698(10) 0.0635(10) 0.0946(12) -0.0063(8) 0.0341(9) -0.0066(8) C22 0.0570(9) 0.0974(14) 0.0835(12) -0.0248(10) 0.0174(8) 0.0124(9) C23 0.0659(10) 0.0684(11) 0.1140(15) -0.0327(10) 0.0111(10) 0.0136(9) C17 0.0645(9) 0.0914(13) 0.0625(9) -0.0075(9) -0.0032(7) 0.0045(9) C16 0.0577(9) 0.1002(14) 0.0779(11) -0.0306(10) 0.0006(8) -0.0056(9) C15 0.0654(10) 0.0648(10) 0.1012(13) -0.0242(9) 0.0146(9) -0.0084(8) C1 0.0871(12) 0.0618(10) 0.0766(11) 0.0080(8) 0.0148(9) -0.0040(9) C12 0.0624(11) 0.0752(12) 0.197(3) -0.0070(14) 0.0437(13) 0.0144(9) O1 0.0890(10) 0.1503(15) 0.1513(15) 0.0771(12) 0.0242(10) 0.0500(9) C4 0.1107(16) 0.0724(13) 0.1301(19) -0.0091(12) 0.0719(15) -0.0149(12) C2 0.149(2) 0.0648(12) 0.0824(13) 0.0117(9) 0.0192(13) -0.0035(12) C3 0.173(3) 0.0625(12) 0.0975(16) -0.0031(11) 0.0727(17) -0.0214(14) _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 N1 C10 1.2764(17) . ? N1 C7 1.4642(17) . ? C9 C13 1.5177(17) . ? C9 C10 1.5197(18) . ? C9 C8 1.5430(18) . ? C13 C14 1.382(2) . ? C13 C18 1.3843(19) . ? C10 C19 1.4813(17) . ? C8 C11 1.509(2) . ? C8 C7 1.5726(19) . ? C19 C20 1.386(2) . ? C19 C24 1.389(2) . ? C7 C6 1.509(2) . ? C20 C21 1.388(2) . ? C6 C1 1.379(2) . ? C6 C5 1.388(2) . ? C18 C17 1.377(2) . ? C24 C23 1.386(2) . ? C14 C15 1.388(2) . ? C11 O1 1.197(2) . ? C11 C12 1.493(3) . ? C21 C22 1.362(2) . ? C5 C4 1.375(3) . ? C22 C23 1.374(3) . ? C17 C16 1.369(3) . ? C16 C15 1.376(3) . ? C1 C2 1.384(3) . ? C4 C3 1.363(3) . ? C2 C3 1.379(3) . ? 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 C10 N1 C7 110.70(11) . . ? C13 C9 C10 116.03(10) . . ? C13 C9 C8 112.39(10) . . ? C10 C9 C8 102.07(10) . . ? C14 C13 C18 118.16(13) . . ? C14 C13 C9 120.38(12) . . ? C18 C13 C9 121.34(12) . . ? N1 C10 C19 120.86(12) . . ? N1 C10 C9 116.07(11) . . ? C19 C10 C9 122.91(11) . . ? C11 C8 C9 113.96(12) . . ? C11 C8 C7 111.27(11) . . ? C9 C8 C7 104.41(10) . . ? C20 C19 C24 118.57(13) . . ? C20 C19 C10 121.04(12) . . ? C24 C19 C10 120.31(13) . . ? N1 C7 C6 111.49(11) . . ? N1 C7 C8 106.36(10) . . ? C6 C7 C8 114.70(11) . . ? C19 C20 C21 120.73(14) . . ? C1 C6 C5 118.49(15) . . ? C1 C6 C7 120.47(13) . . ? C5 C6 C7 121.03(14) . . ? C17 C18 C13 120.90(15) . . ? C23 C24 C19 119.91(16) . . ? C13 C14 C15 120.86(15) . . ? O1 C11 C12 121.32(17) . . ? O1 C11 C8 122.24(15) . . ? C12 C11 C8 116.44(17) . . ? C22 C21 C20 120.21(16) . . ? C4 C5 C6 120.7(2) . . ? C21 C22 C23 119.80(15) . . ? C22 C23 C24 120.77(16) . . ? C16 C17 C18 120.58(16) . . ? C17 C16 C15 119.54(15) . . ? C16 C15 C14 119.96(16) . . ? C6 C1 C2 120.61(19) . . ? C3 C4 C5 120.3(2) . . ? C3 C2 C1 119.8(2) . . ? C4 C3 C2 120.01(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.163 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.028 _database_code_depnum_ccdc_archive 'CCDC 942211' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7.94 H6.53 N0.35 O0.18' _chemical_formula_sum 'C7.94 H6.53 N0.35 O0.18' _chemical_formula_weight 109.72 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 Trigonal _symmetry_space_group_name_H-M P3(2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 9.2770(3) _cell_length_b 9.2770(3) _cell_length_c 34.749(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2589.9(2) _cell_formula_units_Z 17 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 987 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13698 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.1467 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6868 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment . _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(4) _refine_ls_number_reflns 6868 _refine_ls_number_parameters 434 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1998 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1684 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _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 N1 N 0.2821(5) 0.2445(5) 0.07427(11) 0.0580(11) Uani 1 1 d . . . N1A N -0.2840(5) -0.0392(5) 0.22556(11) 0.0587(11) Uani 1 1 d . . . C18 C 0.2608(7) 0.0893(8) 0.13332(15) 0.0613(15) Uani 1 1 d . . . C2 C 0.1744(7) 0.2602(6) 0.05400(14) 0.0583(14) Uani 1 1 d . . . C6A C -0.2061(6) 0.0949(7) 0.28724(14) 0.0570(14) Uani 1 1 d . . . C2A C -0.1769(7) 0.0848(7) 0.24579(14) 0.0568(14) Uani 1 1 d . . . C5A C -0.2294(7) -0.0120(7) 0.18495(14) 0.0609(15) Uani 1 1 d . . . H5AA H -0.2956 0.0271 0.1712 0.073 Uiso 1 1 calc R . . C18A C -0.2594(7) -0.1722(7) 0.16587(15) 0.0605(14) Uani 1 1 d . . . O O -0.0006(7) 0.3701(5) 0.14992(13) 0.0936(12) Uani 1 1 d . . . C6 C 0.2017(6) 0.2975(6) 0.01230(14) 0.0554(14) Uani 1 1 d . . . C3A C -0.0471(6) 0.1306(6) 0.18510(13) 0.0554(13) Uani 1 1 d . . . H3AA H 0.0253 0.0819 0.1860 0.066 Uiso 1 1 calc R . . C5 C 0.2298(7) 0.2176(6) 0.11511(13) 0.0566(14) Uani 1 1 d . . . H5A H 0.2957 0.3229 0.1289 0.068 Uiso 1 1 calc R . . C12 C -0.1434(7) 0.1465(8) 0.05947(15) 0.0616(15) Uani 1 1 d . . . C12A C 0.1405(7) 0.2898(7) 0.24074(16) 0.0622(15) Uani 1 1 d . . . C3 C 0.0450(6) 0.1761(6) 0.11465(14) 0.0564(14) Uani 1 1 d . . . H3A H -0.0264 0.0548 0.1135 0.068 Uiso 1 1 calc R . . C11 C 0.2842(7) 0.2366(7) -0.00941(16) 0.0662(15) Uani 1 1 d . . . H11A H 0.3225 0.1716 0.0021 0.079 Uiso 1 1 calc R . . C11A C -0.2852(6) -0.0474(7) 0.30919(15) 0.0639(15) Uani 1 1 d . . . H11B H -0.3217 -0.1510 0.2980 0.077 Uiso 1 1 calc R . . C10A C -0.3103(7) -0.0357(8) 0.34801(17) 0.0774(17) Uani 1 1 d . . . H10A H -0.3633 -0.1322 0.3627 0.093 Uiso 1 1 calc R . . C7 C 0.1513(8) 0.3971(8) -0.00534(16) 0.0822(19) Uani 1 1 d . . . H7A H 0.0976 0.4407 0.0091 0.099 Uiso 1 1 calc R . . C17A C 0.1872(8) 0.1924(8) 0.26030(18) 0.0833(18) Uani 1 1 d . . . H17A H 0.1087 0.0818 0.2651 0.100 Uiso 1 1 calc R . . C4 C 0.0283(6) 0.2501(6) 0.07598(14) 0.0568(14) Uani 1 1 d . . . H4A H 0.0490 0.3632 0.0805 0.068 Uiso 1 1 calc R . . C4A C -0.0304(6) 0.2208(6) 0.22344(14) 0.0585(14) Uani 1 1 d . . . H4AA H -0.0515 0.3129 0.2188 0.070 Uiso 1 1 calc R . . C19 C 0.1940(9) -0.0670(9) 0.11788(18) 0.088(2) Uani 1 1 d . . . H19A H 0.1296 -0.0933 0.0957 0.105 Uiso 1 1 calc R . . C21 C 0.3172(14) -0.1462(16) 0.1681(4) 0.132(5) Uani 1 1 d . . . H21A H 0.3387 -0.2243 0.1795 0.159 Uiso 1 1 calc R . . C17 C -0.1877(8) 0.0045(9) 0.03908(18) 0.0823(18) Uani 1 1 d . . . H17B H -0.1074 -0.0246 0.0337 0.099 Uiso 1 1 calc R . . C23 C 0.3544(7) 0.1257(9) 0.16696(18) 0.0839(18) Uani 1 1 d . . . H23A H 0.3997 0.2308 0.1780 0.101 Uiso 1 1 calc R . . C7A C -0.1488(8) 0.2477(8) 0.30512(17) 0.0844(19) Uani 1 1 d . . . H7AA H -0.0881 0.3455 0.2912 0.101 Uiso 1 1 calc R . . C10 C 0.3097(7) 0.2722(8) -0.04806(17) 0.0759(17) Uani 1 1 d . . . H10B H 0.3626 0.2281 -0.0626 0.091 Uiso 1 1 calc R . . C23A C -0.1926(8) -0.2615(8) 0.18190(18) 0.0837(19) Uani 1 1 d . . . H23B H -0.1286 -0.2231 0.2041 0.100 Uiso 1 1 calc R . . C24 C -0.0029(7) 0.2393(7) 0.15001(18) 0.0625(12) Uani 1 1 d . . . C19A C -0.3551(7) -0.2313(8) 0.13285(17) 0.0802(18) Uani 1 1 d . . . H19B H -0.4023 -0.1731 0.1219 0.096 Uiso 1 1 calc R . . C9 C 0.2584(8) 0.3714(8) -0.06546(18) 0.0830(18) Uani 1 1 d . . . H9A H 0.2778 0.3957 -0.0916 0.100 Uiso 1 1 calc R . . C16A C 0.3494(10) 0.2550(11) 0.2731(2) 0.104(2) Uani 1 1 d . . . H16A H 0.3771 0.1866 0.2871 0.125 Uiso 1 1 calc R . . C9A C -0.2596(8) 0.1123(9) 0.36491(17) 0.0816(18) Uani 1 1 d . . . H9AA H -0.2776 0.1173 0.3911 0.098 Uiso 1 1 calc R . . C21A C -0.3172(15) -0.4673(10) 0.1322(3) 0.134(4) Uani 1 1 d . . . H21B H -0.3390 -0.5675 0.1212 0.161 Uiso 1 1 calc R . . C13 C -0.2620(9) 0.1910(9) 0.06708(18) 0.090(2) Uani 1 1 d . . . H13A H -0.2324 0.2890 0.0803 0.108 Uiso 1 1 calc R . . C8A C -0.1822(8) 0.2547(9) 0.34392(19) 0.091(2) Uani 1 1 d . . . H8AA H -0.1515 0.3565 0.3554 0.109 Uiso 1 1 calc R . . C22 C 0.3796(11) 0.0061(16) 0.1839(2) 0.120(3) Uani 1 1 d . . . H22A H 0.4407 0.0308 0.2065 0.144 Uiso 1 1 calc R . . C16 C -0.3521(10) -0.0993(10) 0.0260(2) 0.110(3) Uani 1 1 d . . . H16B H -0.3487 -0.1090 -0.0017 0.132 Uiso 1 1 calc R . . H16C H -0.3920 -0.2094 0.0367 0.132 Uiso 1 1 calc R . . C13A C 0.2631(9) 0.4529(8) 0.23368(19) 0.091(2) Uani 1 1 d . . . H13B H 0.2368 0.5240 0.2205 0.109 Uiso 1 1 calc R . . C22A C -0.2211(11) -0.4097(9) 0.1648(3) 0.106(3) Uani 1 1 d . . . H22B H -0.1750 -0.4695 0.1755 0.127 Uiso 1 1 calc R . . C8 C 0.1792(9) 0.4340(9) -0.0444(2) 0.094(2) Uani 1 1 d . . . H8A H 0.1437 0.5013 -0.0560 0.113 Uiso 1 1 calc R . . C20A C -0.3799(10) -0.3773(11) 0.1163(2) 0.118(3) Uani 1 1 d . . . H20A H -0.4411 -0.4147 0.0937 0.141 Uiso 1 1 calc R . . C20 C 0.2213(12) -0.1873(11) 0.1350(3) 0.118(3) Uani 1 1 d . . . H20B H 0.1758 -0.2933 0.1245 0.142 Uiso 1 1 calc R . . C14A C 0.4260(11) 0.5110(11) 0.2463(2) 0.118(3) Uani 1 1 d . . . H14A H 0.5071 0.6203 0.2410 0.141 Uiso 1 1 calc R . . C15A C 0.4678(11) 0.4141(14) 0.2657(3) 0.124(3) Uani 1 1 d . . . H15A H 0.5767 0.4549 0.2740 0.149 Uiso 1 1 calc R . . C15 C -0.4687(10) -0.0513(16) 0.0345(2) 0.125(3) Uani 1 1 d . . . H15B H -0.5777 -0.1170 0.0261 0.150 Uiso 1 1 calc R . . C14 C -0.4268(12) 0.0893(15) 0.0549(3) 0.123(3) Uani 1 1 d . . . H14B H -0.5072 0.1179 0.0607 0.148 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 N1 0.049(3) 0.059(3) 0.063(3) 0.007(2) 0.005(2) 0.026(2) N1A 0.051(3) 0.063(3) 0.061(3) -0.006(2) 0.004(2) 0.027(3) C18 0.048(4) 0.066(4) 0.076(4) 0.018(3) 0.013(3) 0.032(3) C2 0.056(4) 0.056(4) 0.065(4) 0.009(3) 0.005(3) 0.030(3) C6A 0.055(4) 0.053(4) 0.063(4) -0.003(3) 0.007(2) 0.027(3) C2A 0.056(4) 0.055(4) 0.058(3) -0.005(3) 0.004(3) 0.026(3) C5A 0.064(4) 0.062(4) 0.063(3) -0.002(3) -0.002(3) 0.036(3) C18A 0.057(4) 0.051(4) 0.064(4) 0.000(3) 0.018(3) 0.020(3) O 0.151(4) 0.071(3) 0.082(2) 0.019(2) 0.0300(19) 0.072(3) C6 0.054(4) 0.053(3) 0.061(3) 0.009(3) 0.002(2) 0.028(3) C3A 0.059(4) 0.049(3) 0.060(3) 0.001(2) 0.006(2) 0.029(3) C5 0.058(4) 0.051(3) 0.056(3) 0.010(2) 0.007(3) 0.023(3) C12 0.062(4) 0.073(4) 0.061(4) 0.009(3) 0.010(3) 0.042(4) C12A 0.061(4) 0.047(4) 0.065(4) -0.003(3) 0.009(3) 0.017(3) C3 0.043(3) 0.054(3) 0.071(3) 0.008(2) 0.013(2) 0.023(3) C11 0.067(4) 0.073(4) 0.072(4) 0.006(3) 0.000(3) 0.045(4) C11A 0.062(4) 0.056(4) 0.067(4) 0.000(3) 0.007(3) 0.024(3) C10A 0.077(5) 0.076(5) 0.067(4) 0.004(3) 0.009(3) 0.029(4) C7 0.103(5) 0.105(5) 0.066(4) 0.016(3) 0.016(3) 0.073(5) C17A 0.046(4) 0.075(5) 0.103(5) 0.002(4) -0.005(3) 0.011(4) C4 0.063(4) 0.056(4) 0.062(3) 0.009(3) 0.014(3) 0.037(3) C4A 0.061(4) 0.045(3) 0.069(3) 0.002(2) 0.012(3) 0.025(3) C19 0.109(5) 0.074(5) 0.099(5) 0.018(4) 0.023(4) 0.059(4) C21 0.128(9) 0.170(11) 0.162(10) 0.104(9) 0.086(7) 0.122(9) C17 0.064(5) 0.101(5) 0.089(4) -0.002(4) 0.004(3) 0.047(4) C23 0.063(4) 0.115(6) 0.084(5) 0.022(4) 0.008(3) 0.052(4) C7A 0.106(5) 0.065(5) 0.080(5) -0.006(3) 0.012(3) 0.041(4) C10 0.080(5) 0.093(5) 0.068(4) 0.000(3) 0.003(3) 0.054(4) C23A 0.096(5) 0.062(5) 0.098(5) 0.014(4) 0.019(4) 0.044(4) C24 0.066(3) 0.049(4) 0.070(3) 0.003(3) 0.009(2) 0.027(3) C19A 0.072(4) 0.071(5) 0.073(4) -0.006(3) 0.009(3) 0.017(4) C9 0.091(5) 0.098(5) 0.065(4) 0.013(3) 0.017(3) 0.051(5) C16A 0.064(5) 0.116(7) 0.103(6) 0.003(5) -0.009(4) 0.023(5) C9A 0.092(5) 0.088(6) 0.058(4) -0.005(4) 0.011(3) 0.040(4) C21A 0.155(10) 0.060(6) 0.150(9) -0.019(6) 0.083(7) 0.025(6) C13 0.082(5) 0.121(6) 0.097(5) 0.022(4) 0.017(4) 0.074(5) C8A 0.120(6) 0.071(5) 0.074(5) -0.014(4) 0.012(4) 0.042(4) C22 0.108(7) 0.199(10) 0.103(6) 0.078(7) 0.043(5) 0.115(8) C16 0.072(6) 0.135(7) 0.093(6) 0.004(4) -0.001(4) 0.028(5) C13A 0.085(5) 0.053(4) 0.101(5) -0.005(3) 0.013(4) 0.008(4) C22A 0.113(7) 0.057(5) 0.145(7) 0.010(5) 0.049(6) 0.040(5) C8 0.116(6) 0.108(6) 0.086(5) 0.021(4) 0.006(4) 0.077(5) C20A 0.097(6) 0.073(6) 0.113(6) -0.040(5) 0.042(5) -0.010(5) C20 0.125(7) 0.093(6) 0.164(8) 0.035(6) 0.051(6) 0.073(6) C14A 0.078(7) 0.080(6) 0.110(6) -0.009(5) 0.015(5) -0.023(5) C15A 0.079(6) 0.122(8) 0.117(7) -0.007(5) -0.017(5) 0.008(6) C15 0.061(6) 0.216(11) 0.094(6) 0.021(6) 0.004(4) 0.067(7) C14 0.087(7) 0.212(11) 0.109(6) 0.018(6) 0.022(5) 0.104(8) _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 N1 C2 1.289(6) . ? N1 C5 1.480(6) . ? N1A C2A 1.289(6) . ? N1A C5A 1.478(6) . ? C18 C19 1.369(8) . ? C18 C23 1.393(8) . ? C18 C5 1.498(7) . ? C2 C6 1.482(6) . ? C2 C4 1.518(6) . ? C6A C11A 1.376(7) . ? C6A C7A 1.387(7) . ? C6A C2A 1.477(6) . ? C2A C4A 1.526(7) . ? C5A C18A 1.520(7) . ? C5A C3A 1.540(7) . ? C18A C23A 1.376(7) . ? C18A C19A 1.385(8) . ? O C24 1.203(5) . ? C6 C7 1.370(7) . ? C6 C11 1.381(7) . ? C3A C24 1.503(7) . ? C3A C4A 1.540(7) . ? C5 C3 1.557(7) . ? C12 C17 1.366(8) . ? C12 C13 1.381(7) . ? C12 C4 1.503(8) . ? C12A C17A 1.362(8) . ? C12A C13A 1.386(8) . ? C12A C4A 1.507(8) . ? C3 C24 1.520(7) . ? C3 C4 1.552(7) . ? C11 C10 1.375(7) . ? C11A C10A 1.382(7) . ? C10A C9A 1.344(8) . ? C7 C8 1.393(8) . ? C17A C16A 1.388(9) . ? C19 C20 1.396(10) . ? C21 C22 1.347(13) . ? C21 C20 1.385(13) . ? C17 C16 1.411(9) . ? C23 C22 1.375(10) . ? C7A C8A 1.392(8) . ? C10 C9 1.370(8) . ? C23A C22A 1.397(9) . ? C19A C20A 1.381(10) . ? C9 C8 1.356(9) . ? C16A C15A 1.354(11) . ? C9A C8A 1.358(9) . ? C21A C20A 1.351(12) . ? C21A C22A 1.373(13) . ? C13 C14 1.401(11) . ? C16 C15 1.391(11) . ? C13A C14A 1.397(11) . ? C14A C15A 1.326(11) . ? C15 C14 1.359(12) . ? 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 N1 C5 109.6(4) . . ? C2A N1A C5A 108.8(4) . . ? C19 C18 C23 118.9(6) . . ? C19 C18 C5 120.7(5) . . ? C23 C18 C5 120.4(6) . . ? N1 C2 C6 120.6(5) . . ? N1 C2 C4 115.9(4) . . ? C6 C2 C4 123.3(5) . . ? C11A C6A C7A 118.7(5) . . ? C11A C6A C2A 120.4(5) . . ? C7A C6A C2A 120.9(5) . . ? N1A C2A C6A 120.3(5) . . ? N1A C2A C4A 115.5(4) . . ? C6A C2A C4A 124.0(5) . . ? N1A C5A C18A 111.7(4) . . ? N1A C5A C3A 106.2(4) . . ? C18A C5A C3A 115.3(4) . . ? C23A C18A C19A 119.3(6) . . ? C23A C18A C5A 119.6(5) . . ? C19A C18A C5A 121.1(6) . . ? C7 C6 C11 118.5(5) . . ? C7 C6 C2 121.3(5) . . ? C11 C6 C2 120.2(5) . . ? C24 C3A C4A 114.7(4) . . ? C24 C3A C5A 112.8(4) . . ? C4A C3A C5A 103.8(4) . . ? N1 C5 C18 111.2(4) . . ? N1 C5 C3 105.0(4) . . ? C18 C5 C3 115.6(4) . . ? C17 C12 C13 119.2(6) . . ? C17 C12 C4 121.8(5) . . ? C13 C12 C4 118.9(6) . . ? C17A C12A C13A 116.9(6) . . ? C17A C12A C4A 122.2(5) . . ? C13A C12A C4A 120.5(6) . . ? C24 C3 C4 114.5(4) . . ? C24 C3 C5 113.2(4) . . ? C4 C3 C5 103.9(4) . . ? C10 C11 C6 120.0(5) . . ? C6A C11A C10A 119.7(5) . . ? C9A C10A C11A 121.3(6) . . ? C6 C7 C8 121.2(5) . . ? C12A C17A C16A 121.4(7) . . ? C12 C4 C2 118.4(5) . . ? C12 C4 C3 110.9(4) . . ? C2 C4 C3 100.3(4) . . ? C12A C4A C2A 117.5(5) . . ? C12A C4A C3A 112.0(4) . . ? C2A C4A C3A 100.6(4) . . ? C18 C19 C20 120.8(8) . . ? C22 C21 C20 120.4(9) . . ? C12 C17 C16 121.7(6) . . ? C22 C23 C18 120.0(8) . . ? C6A C7A C8A 120.1(6) . . ? C9 C10 C11 121.1(6) . . ? C18A C23A C22A 120.0(7) . . ? O C24 C3A 122.7(5) . . ? O C24 C3 121.7(5) . . ? C3A C24 C3 115.5(4) . . ? C20A C19A C18A 119.5(7) . . ? C8 C9 C10 119.6(6) . . ? C15A C16A C17A 120.8(8) . . ? C10A C9A C8A 120.3(6) . . ? C20A C21A C22A 119.6(9) . . ? C12 C13 C14 120.3(7) . . ? C9A C8A C7A 119.8(6) . . ? C21 C22 C23 121.0(10) . . ? C15 C16 C17 117.5(8) . . ? C12A C13A C14A 120.3(8) . . ? C21A C22A C23A 120.0(9) . . ? C9 C8 C7 119.6(6) . . ? C21A C20A C19A 121.6(9) . . ? C21 C20 C19 118.9(9) . . ? C15A C14A C13A 121.6(8) . . ? C14A C15A C16A 119.0(9) . . ? C14 C15 C16 121.5(8) . . ? C15 C14 C13 119.7(8) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.139 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 942212' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30.50 H24 Cl N O S' _chemical_formula_sum 'C30.50 H24 Cl N O S' _chemical_formula_weight 488.02 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' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 '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 Triclinic _symmetry_space_group_name_H-M P-1 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 39.108(4) _cell_length_b 8.1605(8) _cell_length_c 16.4308(15) _cell_angle_alpha 90.00 _cell_angle_beta 111.789(8) _cell_angle_gamma 90.00 _cell_volume 4869.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2040 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36193 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 27.64 _reflns_number_total 5614 _reflns_number_gt 3632 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment . _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5614 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1272 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 S1 S 0.145464(14) 0.33370(7) 0.20638(3) 0.05710(19) Uani 1 1 d . . . O1 O 0.07175(4) 0.45375(19) -0.06493(8) 0.0611(4) Uani 1 1 d . . . C9 C 0.15424(5) 0.3382(2) 0.10662(12) 0.0478(5) Uani 1 1 d . . . H9A H 0.1804 0.3556 0.1210 0.057 Uiso 1 1 calc R . . H9B H 0.1480 0.2322 0.0782 0.057 Uiso 1 1 calc R . . N1 N 0.17879(4) 0.59924(18) -0.00204(9) 0.0455(4) Uani 1 1 d . . . C18 C 0.20495(5) 0.8051(2) 0.10892(11) 0.0416(4) Uani 1 1 d . . . C17 C 0.17658(5) 0.6820(2) 0.06224(11) 0.0407(4) Uani 1 1 d . . . C8 C 0.13276(5) 0.4712(2) 0.04182(10) 0.0397(4) Uani 1 1 d . . . C10 C 0.14274(5) 0.6463(2) 0.08412(11) 0.0396(4) Uani 1 1 d . . . H10 H 0.1496 0.6394 0.1478 0.047 Uiso 1 1 calc R . . C24 C 0.14716(5) 0.4871(2) -0.03514(11) 0.0424(4) Uani 1 1 d . . . H24A H 0.1280 0.5425 -0.0837 0.051 Uiso 1 1 calc R . . C7 C 0.09163(5) 0.4335(2) 0.01127(11) 0.0425(4) Uani 1 1 d . . . C1 C 0.09739(5) 0.3324(2) 0.16318(12) 0.0472(5) Uani 1 1 d . . . C25 C 0.15701(5) 0.3309(2) -0.07117(11) 0.0448(4) Uani 1 1 d . . . C11 C 0.11286(5) 0.7739(2) 0.04604(11) 0.0418(4) Uani 1 1 d . . . C6 C 0.07615(5) 0.3754(2) 0.07649(12) 0.0439(4) Uani 1 1 d . . . C19 C 0.19957(6) 0.9201(2) 0.16516(12) 0.0539(5) Uani 1 1 d . . . H19 H 0.1777 0.9201 0.1754 0.065 Uiso 1 1 calc R . . C23 C 0.23820(5) 0.8054(2) 0.09598(12) 0.0492(5) Uani 1 1 d . . . H23 H 0.2424 0.7268 0.0598 0.059 Uiso 1 1 calc R . . C22 C 0.26486(6) 0.9205(3) 0.13602(12) 0.0577(5) Uani 1 1 d . . . H22 H 0.2867 0.9206 0.1259 0.069 Uiso 1 1 calc R . . C16 C 0.10949(6) 0.8626(2) -0.02895(12) 0.0537(5) Uani 1 1 d . . . H16 H 0.1269 0.8494 -0.0547 0.064 Uiso 1 1 calc R . . C12 C 0.08707(6) 0.8003(3) 0.08394(13) 0.0528(5) Uani 1 1 d . . . H12 H 0.0890 0.7436 0.1345 0.063 Uiso 1 1 calc R . . C5 C 0.03772(5) 0.3658(3) 0.04995(14) 0.0547(5) Uani 1 1 d . . . H5 H 0.0232 0.3917 -0.0077 0.066 Uiso 1 1 calc R . . C30 C 0.13182(6) 0.2565(3) -0.14450(12) 0.0555(5) Uani 1 1 d . . . H30 H 0.1087 0.3031 -0.1720 0.067 Uiso 1 1 calc R . . C2 C 0.07993(7) 0.2858(3) 0.22002(15) 0.0630(6) Uani 1 1 d . . . H2 H 0.0940 0.2595 0.2779 0.076 Uiso 1 1 calc R . . C26 C 0.19167(6) 0.2610(3) -0.03312(13) 0.0568(5) Uani 1 1 d . . . H26 H 0.2093 0.3108 0.0152 0.068 Uiso 1 1 calc R . . C13 C 0.05857(6) 0.9101(3) 0.04735(15) 0.0672(6) Uani 1 1 d . . . H13 H 0.0416 0.9276 0.0738 0.081 Uiso 1 1 calc R . . C14 C 0.05512(6) 0.9936(3) -0.02782(16) 0.0653(6) Uani 1 1 d . . . H14 H 0.0356 1.0656 -0.0530 0.078 Uiso 1 1 calc R . . C15 C 0.08055(6) 0.9701(3) -0.06542(14) 0.0634(6) Uani 1 1 d . . . H15 H 0.0784 1.0271 -0.1161 0.076 Uiso 1 1 calc R . . C20 C 0.22651(6) 1.0345(3) 0.20603(14) 0.0650(6) Uani 1 1 d . . . H20 H 0.2227 1.1113 0.2437 0.078 Uiso 1 1 calc R . . C21 C 0.25915(6) 1.0354(3) 0.19105(13) 0.0630(6) Uani 1 1 d . . . H21 H 0.2771 1.1134 0.2181 0.076 Uiso 1 1 calc R . . C28 C 0.17489(7) 0.0432(3) -0.13791(15) 0.0670(6) Uani 1 1 d . . . H28 H 0.1807 -0.0537 -0.1596 0.080 Uiso 1 1 calc R . . C27 C 0.20027(7) 0.1174(3) -0.06644(14) 0.0646(6) Uani 1 1 d . . . H27 H 0.2235 0.0711 -0.0399 0.078 Uiso 1 1 calc R . . C29 C 0.14064(7) 0.1131(3) -0.17760(14) 0.0688(6) Uani 1 1 d . . . H29 H 0.1234 0.0639 -0.2268 0.083 Uiso 1 1 calc R . . C4 C 0.02098(7) 0.3194(3) 0.10611(18) 0.0708(6) Uani 1 1 d . . . H4 H -0.0046 0.3154 0.0870 0.085 Uiso 1 1 calc R . . C3 C 0.04240(7) 0.2786(3) 0.19170(18) 0.0731(7) Uani 1 1 d . . . H3 H 0.0312 0.2460 0.2301 0.088 Uiso 1 1 calc R . . Cl1 Cl 0.02755(2) 0.76272(15) 0.21131(6) 0.1282(4) Uani 1 1 d . . . C31 C 0.0000 0.6477(5) 0.2500 0.0784(10) Uani 1 2 d S . . H31A H 0.0155 0.5776 0.2968 0.094 Uiso 0.50 1 calc PR . . H31B H -0.0155 0.5776 0.2032 0.094 Uiso 0.50 1 calc PR . . 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 0.0474(3) 0.0708(4) 0.0488(3) 0.0183(2) 0.0128(2) 0.0025(3) O1 0.0438(8) 0.0819(11) 0.0472(7) 0.0034(7) 0.0048(6) -0.0025(7) C9 0.0404(10) 0.0477(11) 0.0535(11) 0.0092(8) 0.0154(9) 0.0039(9) N1 0.0479(9) 0.0431(8) 0.0489(8) -0.0041(7) 0.0216(7) -0.0035(7) C18 0.0423(10) 0.0396(9) 0.0420(9) 0.0020(7) 0.0144(8) -0.0007(8) C17 0.0405(10) 0.0395(9) 0.0435(9) 0.0025(7) 0.0172(8) 0.0017(8) C8 0.0370(10) 0.0401(9) 0.0400(9) 0.0012(7) 0.0122(7) 0.0002(8) C10 0.0396(10) 0.0435(9) 0.0355(8) 0.0012(7) 0.0138(7) -0.0001(8) C24 0.0432(10) 0.0407(10) 0.0423(9) -0.0011(8) 0.0148(8) -0.0021(8) C7 0.0406(10) 0.0384(9) 0.0449(10) 0.0001(7) 0.0116(8) 0.0019(8) C1 0.0481(11) 0.0403(10) 0.0544(11) 0.0060(8) 0.0204(9) -0.0004(9) C25 0.0503(11) 0.0442(10) 0.0423(9) -0.0012(8) 0.0200(9) -0.0017(9) C11 0.0416(10) 0.0393(9) 0.0437(10) -0.0029(7) 0.0147(8) -0.0003(8) C6 0.0403(10) 0.0393(9) 0.0526(10) -0.0020(8) 0.0176(8) -0.0032(8) C19 0.0480(12) 0.0560(12) 0.0581(11) -0.0100(10) 0.0204(10) -0.0045(10) C23 0.0473(12) 0.0538(11) 0.0491(10) -0.0004(9) 0.0207(9) -0.0014(9) C22 0.0426(11) 0.0725(14) 0.0550(11) 0.0052(11) 0.0145(9) -0.0073(11) C16 0.0569(12) 0.0542(12) 0.0532(11) 0.0082(9) 0.0241(10) 0.0069(10) C12 0.0534(12) 0.0542(12) 0.0556(11) 0.0003(9) 0.0256(10) 0.0038(10) C5 0.0414(11) 0.0545(12) 0.0660(12) -0.0037(10) 0.0175(10) -0.0004(9) C30 0.0587(14) 0.0576(12) 0.0468(11) -0.0040(9) 0.0155(10) -0.0035(10) C2 0.0678(16) 0.0644(13) 0.0652(13) 0.0133(11) 0.0346(12) 0.0040(12) C26 0.0543(13) 0.0587(12) 0.0548(11) -0.0091(10) 0.0172(10) 0.0018(11) C13 0.0579(14) 0.0631(14) 0.0884(16) -0.0011(13) 0.0362(12) 0.0105(12) C14 0.0527(13) 0.0534(12) 0.0817(15) 0.0049(11) 0.0156(12) 0.0142(11) C15 0.0702(15) 0.0522(12) 0.0644(13) 0.0160(10) 0.0213(12) 0.0120(11) C20 0.0635(14) 0.0574(13) 0.0685(13) -0.0189(11) 0.0183(11) -0.0036(11) C21 0.0562(14) 0.0597(13) 0.0621(13) -0.0069(10) 0.0092(11) -0.0144(11) C28 0.0955(19) 0.0485(12) 0.0682(14) -0.0093(11) 0.0436(14) 0.0001(13) C27 0.0716(15) 0.0561(13) 0.0730(14) 0.0019(11) 0.0347(13) 0.0136(12) C29 0.0894(18) 0.0635(14) 0.0535(12) -0.0179(10) 0.0264(12) -0.0144(14) C4 0.0485(13) 0.0737(16) 0.0973(18) -0.0020(13) 0.0353(13) -0.0061(12) C3 0.0711(17) 0.0728(15) 0.0945(18) 0.0119(13) 0.0529(15) 0.0000(13) Cl1 0.0826(6) 0.1952(10) 0.1056(6) 0.0415(6) 0.0334(5) -0.0156(6) C31 0.069(2) 0.097(3) 0.064(2) 0.000 0.0199(17) 0.000 _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 C1 1.746(2) . ? S1 C9 1.7956(19) . ? O1 C7 1.215(2) . ? C9 C8 1.534(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N1 C17 1.283(2) . ? N1 C24 1.471(2) . ? C18 C19 1.387(2) . ? C18 C23 1.394(3) . ? C18 C17 1.482(2) . ? C17 C10 1.523(2) . ? C8 C7 1.528(2) . ? C8 C24 1.569(2) . ? C8 C10 1.573(2) . ? C10 C11 1.516(2) . ? C10 H10 0.9800 . ? C24 C25 1.514(2) . ? C24 H24A 0.9800 . ? C7 C6 1.490(2) . ? C1 C2 1.399(3) . ? C1 C6 1.401(3) . ? C25 C30 1.382(3) . ? C25 C26 1.387(3) . ? C11 C12 1.385(3) . ? C11 C16 1.393(2) . ? C6 C5 1.403(3) . ? C19 C20 1.382(3) . ? C19 H19 0.9300 . ? C23 C22 1.376(3) . ? C23 H23 0.9300 . ? C22 C21 1.377(3) . ? C22 H22 0.9300 . ? C16 C15 1.381(3) . ? C16 H16 0.9300 . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C5 C4 1.368(3) . ? C5 H5 0.9300 . ? C30 C29 1.387(3) . ? C30 H30 0.9300 . ? C2 C3 1.366(3) . ? C2 H2 0.9300 . ? C26 C27 1.387(3) . ? C26 H26 0.9300 . ? C13 C14 1.373(3) . ? C13 H13 0.9300 . ? C14 C15 1.365(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C20 C21 1.387(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C28 C27 1.366(3) . ? C28 C29 1.377(3) . ? C28 H28 0.9300 . ? C27 H27 0.9300 . ? C29 H29 0.9300 . ? C4 C3 1.384(3) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? Cl1 C31 1.719(2) . ? C31 Cl1 1.719(2) 2 ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? 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 C1 S1 C9 99.84(9) . . ? C8 C9 S1 114.01(13) . . ? C8 C9 H9A 108.7 . . ? S1 C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? S1 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C17 N1 C24 109.12(15) . . ? C19 C18 C23 118.78(17) . . ? C19 C18 C17 122.27(17) . . ? C23 C18 C17 118.94(16) . . ? N1 C17 C18 121.10(16) . . ? N1 C17 C10 115.05(16) . . ? C18 C17 C10 123.83(15) . . ? C7 C8 C9 108.88(14) . . ? C7 C8 C24 113.63(13) . . ? C9 C8 C24 110.48(14) . . ? C7 C8 C10 112.74(14) . . ? C9 C8 C10 110.72(14) . . ? C24 C8 C10 100.18(13) . . ? C11 C10 C17 112.03(14) . . ? C11 C10 C8 114.50(14) . . ? C17 C10 C8 99.46(14) . . ? C11 C10 H10 110.1 . . ? C17 C10 H10 110.1 . . ? C8 C10 H10 110.1 . . ? N1 C24 C25 111.54(15) . . ? N1 C24 C8 104.92(13) . . ? C25 C24 C8 117.71(14) . . ? N1 C24 H24A 107.4 . . ? C25 C24 H24A 107.4 . . ? C8 C24 H24A 107.4 . . ? O1 C7 C6 120.58(16) . . ? O1 C7 C8 120.26(16) . . ? C6 C7 C8 119.14(14) . . ? C2 C1 C6 119.64(19) . . ? C2 C1 S1 116.70(15) . . ? C6 C1 S1 123.66(14) . . ? C30 C25 C26 118.24(18) . . ? C30 C25 C24 120.54(18) . . ? C26 C25 C24 121.20(17) . . ? C12 C11 C16 118.13(18) . . ? C12 C11 C10 119.99(16) . . ? C16 C11 C10 121.84(16) . . ? C1 C6 C5 117.66(17) . . ? C1 C6 C7 124.39(16) . . ? C5 C6 C7 117.94(16) . . ? C20 C19 C18 120.3(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C22 C23 C18 120.84(18) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? C23 C22 C21 120.0(2) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C15 C16 C11 120.49(19) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C13 C12 C11 120.66(19) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C4 C5 C6 122.1(2) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C25 C30 C29 120.8(2) . . ? C25 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C27 C26 C25 120.6(2) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.5(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.7(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 119.8(2) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C27 C28 C29 119.5(2) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C28 C27 C26 120.6(2) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C28 C29 C30 120.2(2) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C2 C3 C4 120.3(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? Cl1 C31 Cl1 113.8(2) . 2 ? Cl1 C31 H31A 108.8 . . ? Cl1 C31 H31A 108.8 2 . ? Cl1 C31 H31B 108.8 . . ? Cl1 C31 H31B 108.8 2 . ? H31A C31 H31B 107.7 . . ? 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 C1 S1 C9 C8 50.13(15) . . . . ? C24 N1 C17 C18 179.84(15) . . . . ? C24 N1 C17 C10 -1.5(2) . . . . ? C19 C18 C17 N1 165.84(17) . . . . ? C23 C18 C17 N1 -14.2(3) . . . . ? C19 C18 C17 C10 -12.7(3) . . . . ? C23 C18 C17 C10 167.24(16) . . . . ? S1 C9 C8 C7 -64.61(17) . . . . ? S1 C9 C8 C24 169.94(12) . . . . ? S1 C9 C8 C10 59.88(18) . . . . ? N1 C17 C10 C11 -99.61(18) . . . . ? C18 C17 C10 C11 79.0(2) . . . . ? N1 C17 C10 C8 21.78(19) . . . . ? C18 C17 C10 C8 -159.59(15) . . . . ? C7 C8 C10 C11 -31.80(19) . . . . ? C9 C8 C10 C11 -154.06(15) . . . . ? C24 C8 C10 C11 89.33(16) . . . . ? C7 C8 C10 C17 -151.38(14) . . . . ? C9 C8 C10 C17 86.36(16) . . . . ? C24 C8 C10 C17 -30.26(15) . . . . ? C17 N1 C24 C25 -148.48(15) . . . . ? C17 N1 C24 C8 -19.97(18) . . . . ? C7 C8 C24 N1 152.04(14) . . . . ? C9 C8 C24 N1 -85.24(16) . . . . ? C10 C8 C24 N1 31.55(16) . . . . ? C7 C8 C24 C25 -83.26(19) . . . . ? C9 C8 C24 C25 39.5(2) . . . . ? C10 C8 C24 C25 156.25(15) . . . . ? C9 C8 C7 O1 -139.81(18) . . . . ? C24 C8 C7 O1 -16.2(2) . . . . ? C10 C8 C7 O1 96.9(2) . . . . ? C9 C8 C7 C6 41.6(2) . . . . ? C24 C8 C7 C6 165.23(15) . . . . ? C10 C8 C7 C6 -81.64(19) . . . . ? C9 S1 C1 C2 163.62(16) . . . . ? C9 S1 C1 C6 -16.65(18) . . . . ? N1 C24 C25 C30 -142.88(17) . . . . ? C8 C24 C25 C30 95.8(2) . . . . ? N1 C24 C25 C26 35.5(2) . . . . ? C8 C24 C25 C26 -85.8(2) . . . . ? C17 C10 C11 C12 -155.52(17) . . . . ? C8 C10 C11 C12 92.2(2) . . . . ? C17 C10 C11 C16 27.1(2) . . . . ? C8 C10 C11 C16 -85.2(2) . . . . ? C2 C1 C6 C5 -1.5(3) . . . . ? S1 C1 C6 C5 178.78(15) . . . . ? C2 C1 C6 C7 177.36(18) . . . . ? S1 C1 C6 C7 -2.4(3) . . . . ? O1 C7 C6 C1 172.99(18) . . . . ? C8 C7 C6 C1 -8.5(3) . . . . ? O1 C7 C6 C5 -8.2(3) . . . . ? C8 C7 C6 C5 170.38(17) . . . . ? C23 C18 C19 C20 1.3(3) . . . . ? C17 C18 C19 C20 -178.76(18) . . . . ? C19 C18 C23 C22 -1.9(3) . . . . ? C17 C18 C23 C22 178.10(17) . . . . ? C18 C23 C22 C21 1.3(3) . . . . ? C12 C11 C16 C15 -1.8(3) . . . . ? C10 C11 C16 C15 175.65(18) . . . . ? C16 C11 C12 C13 0.9(3) . . . . ? C10 C11 C12 C13 -176.64(18) . . . . ? C1 C6 C5 C4 1.3(3) . . . . ? C7 C6 C5 C4 -177.66(19) . . . . ? C26 C25 C30 C29 1.8(3) . . . . ? C24 C25 C30 C29 -179.76(18) . . . . ? C6 C1 C2 C3 1.3(3) . . . . ? S1 C1 C2 C3 -178.94(18) . . . . ? C30 C25 C26 C27 -1.9(3) . . . . ? C24 C25 C26 C27 179.62(18) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C11 C16 C15 C14 1.2(3) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? C23 C22 C21 C20 0.1(3) . . . . ? C19 C20 C21 C22 -0.7(3) . . . . ? C29 C28 C27 C26 0.7(3) . . . . ? C25 C26 C27 C28 0.7(3) . . . . ? C27 C28 C29 C30 -0.9(3) . . . . ? C25 C30 C29 C28 -0.4(3) . . . . ? C6 C5 C4 C3 -0.8(3) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C5 C4 C3 C2 0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.451 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 942213'