# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_SA1 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C17 H20 N2 O2' _chemical_formula_sum 'C51 H60 N6 O6' _chemical_melting_point ? _exptl_crystal_description rectangular _exptl_crystal_colour yellow _diffrn_ambient_temperature 293(2) _chemical_formula_weight 853.05 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' 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' N N 0.0061 0.0033 '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' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7339(7) _cell_length_b 12.1454(7) _cell_length_c 17.3108(9) _cell_angle_alpha 97.141(4) _cell_angle_beta 105.326(5) _cell_angle_gamma 101.489(5) _cell_volume 2290.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3302 _cell_measurement_theta_min 3.4242 _cell_measurement_theta_max 29.1795 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912.0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92705 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9241 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.4242 _diffrn_reflns_theta_max 29.1795 _reflns_number_total 4266 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. ; _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^)+(0.0662P)^2^+0.8236P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4266 _refine_ls_number_parameters 588 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.001 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 0.12592(19) 0.27042(17) 0.33166(13) 0.0514(6) Uani 1 1 d . . . O2 O 0.2556(2) 0.17414(17) 0.84038(13) 0.0524(6) Uani 1 1 d . . . N3 N 0.1862(3) 0.0075(2) 0.91947(19) 0.0426(7) Uani 1 1 d . . . O4 O 0.3982(2) 0.4516(2) 0.30992(15) 0.0640(7) Uani 1 1 d . . . H4 H 0.4529 0.4291 0.2966 0.096 Uiso 1 1 calc R . . O5 O 0.2267(2) 0.34448(18) 0.76681(15) 0.0590(7) Uani 1 1 d . . . H5 H 0.2324 0.2887 0.7885 0.089 Uiso 1 1 calc R . . N6 N 0.2778(3) 0.4643(2) 0.41894(19) 0.0454(7) Uani 1 1 d . . . O7 O 0.0108(2) -0.1229(2) 0.79089(13) 0.0647(7) Uani 1 1 d . . . H7 H -0.0369 -0.1746 0.7551 0.097 Uiso 1 1 calc R . . N8 N 0.1973(3) 0.5497(3) 0.73897(16) 0.0484(8) Uani 1 1 d . . . N9 N 0.6319(3) 0.9970(2) 0.78659(17) 0.0578(8) Uani 1 1 d . . . O10 O 0.4185(2) 0.6032(2) 0.72363(16) 0.0693(7) Uani 1 1 d . . . C11 C 0.3613(3) 0.1998(2) 0.89469(19) 0.0432(8) Uani 1 1 d . . . C12 C 0.2106(3) 0.6620(3) 0.75252(18) 0.0478(9) Uani 1 1 d . . . H12 H 0.1449 0.6891 0.7601 0.057 Uiso 1 1 calc R . . C13 C 0.3853(3) 0.1359(3) 0.95938(18) 0.0440(8) Uani 1 1 d . . . C14 C 0.0955(3) -0.0775(2) 0.93191(19) 0.0413(8) Uani 1 1 d . . . C15 C -0.0225(3) 0.1775(3) 0.38594(19) 0.0476(9) Uani 1 1 d . . . H15 H -0.0428 0.1140 0.3445 0.057 Uiso 1 1 calc R . . C16 C 0.5289(3) 0.9125(3) 0.77417(19) 0.0475(9) Uani 1 1 d . . . C17 C 0.0705(3) 0.2700(3) 0.38793(19) 0.0416(8) Uani 1 1 d . . . C18 C 0.2054(3) 0.4558(3) 0.4655(2) 0.0503(9) Uani 1 1 d . . . H18 H 0.2227 0.5148 0.5098 0.060 Uiso 1 1 calc R . . C19 C 0.3205(3) 0.8597(3) 0.77680(19) 0.0502(9) Uani 1 1 d . . . H19 H 0.2520 0.8814 0.7845 0.060 Uiso 1 1 calc R . . C20 C 0.0057(3) -0.1449(3) 0.8646(2) 0.0441(8) Uani 1 1 d . . . C21 C 0.2973(3) 0.0475(3) 0.9681(2) 0.0467(9) Uani 1 1 d . . . H21 H 0.3195 0.0132 1.0131 0.056 Uiso 1 1 calc R . . C22 C 0.3847(3) 0.5486(3) 0.4314(2) 0.0474(9) Uani 1 1 d . . . C23 C 0.3152(3) 0.7424(3) 0.75626(19) 0.0446(8) Uani 1 1 d . . . C24 C 0.1136(3) 0.3607(3) 0.75534(19) 0.0484(9) Uani 1 1 d . . . C25 C 0.1053(3) 0.3655(3) 0.45377(19) 0.0455(9) Uani 1 1 d . . . C26 C 0.0954(3) 0.4661(3) 0.73954(19) 0.0458(9) Uani 1 1 d . . . C27 C 0.4203(3) 0.7106(3) 0.7428(2) 0.0511(9) Uani 1 1 d . . . C28 C 0.4563(3) 0.2902(3) 0.8940(2) 0.0508(9) Uani 1 1 d . . . H28 H 0.4420 0.3336 0.8534 0.061 Uiso 1 1 calc R . . C29 C 0.4221(3) 0.9418(3) 0.78564(19) 0.0512(9) Uani 1 1 d . . . H29 H 0.4222 1.0183 0.7994 0.061 Uiso 1 1 calc R . . C30 C 0.5236(3) 0.7974(3) 0.7510(2) 0.0552(9) Uani 1 1 d . . . H30 H 0.5912 0.7773 0.7405 0.066 Uiso 1 1 calc R . . N31 N -0.1741(3) 0.0817(3) 0.4402(2) 0.0694(9) Uani 1 1 d . . . C32 C -0.0863(3) 0.1756(3) 0.4429(2) 0.0536(9) Uani 1 1 d . . . C33 C 0.7405(3) 0.9699(3) 0.7699(2) 0.0642(11) Uani 1 1 d . . . H33A H 0.7477 0.8966 0.7847 0.077 Uiso 1 1 calc R . . H33B H 0.8118 1.0272 0.8044 0.077 Uiso 1 1 calc R . . C34 C 0.4471(3) 0.5399(3) 0.3738(2) 0.0505(9) Uani 1 1 d . . . C35 C -0.0190(3) 0.4871(3) 0.7268(2) 0.0620(10) Uani 1 1 d . . . H35 H -0.0310 0.5574 0.7152 0.074 Uiso 1 1 calc R . . C36 C 0.5029(3) 0.1659(3) 1.0162(2) 0.0613(10) Uani 1 1 d . . . H36 H 0.5192 0.1243 1.0578 0.074 Uiso 1 1 calc R . . C37 C -0.0848(3) -0.2281(3) 0.8752(2) 0.0583(10) Uani 1 1 d . . . H37 H -0.1455 -0.2739 0.8302 0.070 Uiso 1 1 calc R . . C38 C -0.2041(3) -0.0227(3) 0.3791(2) 0.0662(11) Uani 1 1 d . . . H38A H -0.2008 -0.0021 0.3272 0.079 Uiso 1 1 calc R . . H38B H -0.2868 -0.0646 0.3722 0.079 Uiso 1 1 calc R . . C39 C 0.0165(3) 0.2781(3) 0.7589(2) 0.0657(11) Uani 1 1 d . . . H39 H 0.0275 0.2070 0.7692 0.079 Uiso 1 1 calc R . . C40 C 0.0935(3) -0.0930(3) 1.0089(2) 0.0609(10) Uani 1 1 d . . . H40 H 0.1535 -0.0471 1.0543 0.073 Uiso 1 1 calc R . . C41 C 0.5545(3) 0.6192(3) 0.3832(3) 0.0676(11) Uani 1 1 d . . . H41 H 0.5953 0.6143 0.3441 0.081 Uiso 1 1 calc R . . C42 C -0.1154(3) 0.4050(4) 0.7312(2) 0.0774(12) Uani 1 1 d . . . H42 H -0.1920 0.4197 0.7235 0.093 Uiso 1 1 calc R . . C43 C -0.0556(4) 0.2746(3) 0.5051(2) 0.0671(11) Uani 1 1 d . . . H43 H -0.0996 0.2777 0.5425 0.081 Uiso 1 1 calc R . . C44 C 0.5689(3) 0.3172(3) 0.9502(2) 0.0664(11) Uani 1 1 d . . . N45 N 0.6579(3) 0.4051(3) 0.9469(2) 0.1045(14) Uani 1 1 d . . . C46 C 0.0029(4) -0.1766(3) 1.0192(2) 0.0753(12) Uani 1 1 d . . . H46 H 0.0017 -0.1873 1.0712 0.090 Uiso 1 1 calc R . . C47 C 0.6344(3) 1.1181(3) 0.8070(2) 0.0672(11) Uani 1 1 d . . . H47A H 0.7184 1.1606 0.8318 0.081 Uiso 1 1 calc R . . H47B H 0.5916 1.1272 0.8474 0.081 Uiso 1 1 calc R . . C48 C 0.0365(4) 0.3636(3) 0.5099(2) 0.0630(11) Uani 1 1 d . . . H48 H 0.0559 0.4264 0.5518 0.076 Uiso 1 1 calc R . . C49 C 0.4336(4) 0.6344(3) 0.4994(3) 0.0778(12) Uani 1 1 d . . . H49 H 0.3942 0.6397 0.5393 0.093 Uiso 1 1 calc R . . C50 C 0.5784(4) 1.1700(3) 0.7356(2) 0.0787(12) Uani 1 1 d . . . H50A H 0.6163 1.1571 0.6936 0.118 Uiso 1 1 calc R . . H50B H 0.5907 1.2507 0.7533 0.118 Uiso 1 1 calc R . . H50C H 0.4927 1.1351 0.7147 0.118 Uiso 1 1 calc R . . C51 C -0.1195(4) -0.0983(3) 0.4021(2) 0.0814(12) Uani 1 1 d . . . H51A H -0.1480 -0.1691 0.3635 0.122 Uiso 1 1 calc R . . H51B H -0.1169 -0.1133 0.4556 0.122 Uiso 1 1 calc R . . H51C H -0.0394 -0.0610 0.4019 0.122 Uiso 1 1 calc R . . C52 C -0.0850(4) -0.2432(3) 0.9523(3) 0.0732(12) Uani 1 1 d . . . H52 H -0.1459 -0.2996 0.9591 0.088 Uiso 1 1 calc R . . C53 C -0.0961(4) 0.3005(4) 0.7472(3) 0.0833(13) Uani 1 1 d . . . H53 H -0.1608 0.2444 0.7501 0.100 Uiso 1 1 calc R . . C54 C 0.6416(4) 0.4789(3) 0.8866(3) 0.0765(12) Uani 1 1 d . . . H54A H 0.5915 0.4332 0.8342 0.092 Uiso 1 1 calc R . . H54B H 0.7204 0.5134 0.8810 0.092 Uiso 1 1 calc R . . C55 C 0.6003(4) 0.7044(4) 0.4499(4) 0.0896(15) Uani 1 1 d . . . H55 H 0.6725 0.7578 0.4561 0.108 Uiso 1 1 calc R . . C56 C 0.5915(3) 0.2515(3) 1.0127(2) 0.0762(13) Uani 1 1 d . . . H56 H 0.6679 0.2681 1.0510 0.091 Uiso 1 1 calc R . . C57 C 0.5414(5) 0.7122(4) 0.5081(3) 0.0979(15) Uani 1 1 d . . . H57 H 0.5741 0.7704 0.5538 0.117 Uiso 1 1 calc R . . C58 C 0.7399(4) 0.9651(4) 0.6842(2) 0.0912(14) Uani 1 1 d . . . H58A H 0.6671 0.9122 0.6492 0.137 Uiso 1 1 calc R . . H58B H 0.8098 0.9404 0.6770 0.137 Uiso 1 1 calc R . . H58C H 0.7425 1.0397 0.6707 0.137 Uiso 1 1 calc R . . C59 C -0.2335(4) 0.0723(4) 0.5044(3) 0.0999(15) Uani 1 1 d . . . H59A H -0.2423 -0.0045 0.5160 0.120 Uiso 1 1 calc R . . H59B H -0.1827 0.1252 0.5538 0.120 Uiso 1 1 calc R . . C60 C 0.5837(4) 0.5703(4) 0.9098(3) 0.0958(14) Uani 1 1 d . . . H60A H 0.5815 0.6214 0.8716 0.144 Uiso 1 1 calc R . . H60B H 0.6298 0.6121 0.9635 0.144 Uiso 1 1 calc R . . H60C H 0.5021 0.5368 0.9093 0.144 Uiso 1 1 calc R . . C61 C -0.3530(6) 0.0972(6) 0.4806(4) 0.176(3) Uani 1 1 d . . . H61A H -0.4057 0.0409 0.4346 0.265 Uiso 1 1 calc R . . H61B H -0.3451 0.1716 0.4664 0.265 Uiso 1 1 calc R . . H61C H -0.3870 0.0955 0.5253 0.265 Uiso 1 1 calc R . . C63 C 0.7810(8) 0.4714(5) 1.0388(4) 0.157(3) Uani 1 1 d . . . H63A H 0.8108 0.5533 1.0445 0.189 Uiso 1 1 calc R . . H63B H 0.7665 0.4511 1.0885 0.189 Uiso 1 1 calc R . . C74 C 0.8401(8) 0.4123(7) 1.0084(6) 0.239(6) Uani 1 1 d . . . H74A H 0.9212 0.4265 1.0447 0.359 Uiso 1 1 calc R . . H74B H 0.8438 0.4325 0.9570 0.359 Uiso 1 1 calc R . . H74C H 0.8006 0.3327 1.0000 0.359 Uiso 1 1 calc R . . H8 H 0.263(3) 0.525(3) 0.7327(19) 0.061(12) Uiso 1 1 d . . . H3 H 0.171(3) 0.039(2) 0.8780(19) 0.045(10) Uiso 1 1 d . . . H6 H 0.258(3) 0.405(3) 0.374(2) 0.094(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0511(15) 0.0549(14) 0.0438(14) 0.0015(11) 0.0194(12) 0.0003(11) O2 0.0442(16) 0.0498(14) 0.0524(14) 0.0175(11) -0.0001(13) 0.0015(11) N3 0.042(2) 0.0429(17) 0.0373(18) 0.0113(15) 0.0068(16) 0.0027(15) O4 0.0453(15) 0.0741(17) 0.0667(17) -0.0007(15) 0.0198(13) 0.0053(13) O5 0.0425(16) 0.0558(16) 0.0817(18) 0.0327(13) 0.0149(12) 0.0113(11) N6 0.047(2) 0.0394(18) 0.0456(19) 0.0014(16) 0.0115(16) 0.0072(15) O7 0.0578(18) 0.0750(18) 0.0422(15) 0.0049(13) 0.0078(12) -0.0138(12) N8 0.039(2) 0.049(2) 0.061(2) 0.0213(15) 0.0158(15) 0.0113(17) N9 0.045(2) 0.057(2) 0.074(2) 0.0190(16) 0.0208(16) 0.0072(16) O10 0.0582(17) 0.0469(17) 0.112(2) 0.0143(14) 0.0432(15) 0.0104(12) C11 0.042(2) 0.038(2) 0.044(2) 0.0049(17) 0.0063(19) 0.0076(17) C12 0.043(2) 0.056(3) 0.049(2) 0.0198(18) 0.0141(17) 0.0157(19) C13 0.042(2) 0.040(2) 0.042(2) 0.0111(17) 0.0041(18) 0.0015(17) C14 0.047(2) 0.038(2) 0.037(2) 0.0082(18) 0.0135(19) 0.0030(18) C15 0.051(2) 0.052(2) 0.043(2) 0.0132(17) 0.0183(19) 0.0112(19) C16 0.040(2) 0.051(3) 0.054(2) 0.0215(18) 0.0157(17) 0.0078(19) C17 0.040(2) 0.049(2) 0.041(2) 0.0150(19) 0.0130(18) 0.0155(18) C18 0.064(3) 0.043(2) 0.047(2) 0.0041(17) 0.018(2) 0.020(2) C19 0.046(2) 0.057(3) 0.055(2) 0.0174(18) 0.0186(18) 0.020(2) C20 0.045(2) 0.046(2) 0.040(2) 0.0099(18) 0.0144(19) 0.0039(18) C21 0.050(3) 0.047(2) 0.041(2) 0.0134(17) 0.007(2) 0.0126(19) C22 0.049(2) 0.034(2) 0.052(2) 0.0035(19) 0.006(2) 0.0091(19) C23 0.040(2) 0.047(2) 0.052(2) 0.0187(17) 0.0177(17) 0.0117(19) C24 0.036(2) 0.055(2) 0.051(2) 0.0217(18) 0.0071(17) 0.0051(19) C25 0.058(2) 0.040(2) 0.046(2) 0.0101(18) 0.0211(19) 0.0201(19) C26 0.036(2) 0.051(2) 0.050(2) 0.0223(17) 0.0111(17) 0.0043(19) C27 0.053(3) 0.045(2) 0.060(2) 0.0180(18) 0.0231(19) 0.010(2) C28 0.043(2) 0.046(2) 0.056(2) 0.0200(17) 0.0031(19) 0.0035(18) C29 0.052(3) 0.044(2) 0.061(2) 0.0174(17) 0.0181(19) 0.013(2) C30 0.046(2) 0.051(3) 0.078(3) 0.0200(19) 0.0297(19) 0.0146(19) N31 0.065(2) 0.074(2) 0.082(2) 0.030(2) 0.0416(19) 0.0109(19) C32 0.054(2) 0.056(3) 0.060(3) 0.022(2) 0.023(2) 0.018(2) C33 0.054(3) 0.061(2) 0.069(3) 0.020(2) 0.012(2) -0.0012(19) C34 0.043(2) 0.038(2) 0.062(3) 0.010(2) 0.004(2) 0.0067(19) C35 0.044(3) 0.070(3) 0.074(3) 0.037(2) 0.0124(19) 0.013(2) C36 0.059(3) 0.056(2) 0.058(2) 0.0240(19) -0.001(2) 0.008(2) C37 0.052(2) 0.053(2) 0.057(3) 0.0075(19) 0.0104(19) -0.0070(19) C38 0.049(2) 0.077(3) 0.065(3) 0.028(2) 0.0108(19) -0.002(2) C39 0.048(3) 0.064(3) 0.085(3) 0.037(2) 0.015(2) 0.004(2) C40 0.064(3) 0.066(2) 0.042(2) 0.0113(19) 0.0110(19) -0.003(2) C41 0.049(3) 0.048(2) 0.101(3) 0.024(3) 0.015(2) 0.003(2) C42 0.038(3) 0.094(3) 0.106(3) 0.049(3) 0.019(2) 0.014(2) C43 0.084(3) 0.066(3) 0.077(3) 0.027(2) 0.054(2) 0.028(2) C44 0.036(2) 0.057(2) 0.086(3) 0.030(2) -0.007(2) -0.0111(19) N45 0.043(2) 0.096(3) 0.135(3) 0.067(3) -0.030(2) -0.0223(19) C46 0.087(3) 0.085(3) 0.054(3) 0.027(2) 0.028(3) 0.000(3) C47 0.063(3) 0.048(3) 0.082(3) 0.012(2) 0.018(2) 0.0001(19) C48 0.092(3) 0.052(2) 0.063(3) 0.0116(19) 0.044(2) 0.028(2) C49 0.075(3) 0.056(3) 0.087(3) -0.010(3) 0.017(2) 0.005(2) C50 0.071(3) 0.067(3) 0.097(3) 0.033(2) 0.018(2) 0.015(2) C51 0.077(3) 0.072(3) 0.083(3) 0.015(2) 0.007(2) 0.011(2) C52 0.066(3) 0.070(3) 0.075(3) 0.025(2) 0.023(3) -0.012(2) C53 0.045(3) 0.092(3) 0.113(4) 0.054(3) 0.020(2) -0.001(2) C54 0.062(3) 0.062(3) 0.095(3) 0.030(2) 0.013(2) -0.004(2) C55 0.053(3) 0.045(3) 0.153(5) 0.018(3) 0.008(3) 0.001(2) C56 0.047(3) 0.071(3) 0.086(3) 0.040(2) -0.015(2) -0.009(2) C57 0.074(4) 0.057(3) 0.123(4) -0.025(3) -0.005(3) -0.002(3) C58 0.113(4) 0.087(3) 0.075(3) 0.003(2) 0.033(3) 0.028(3) C59 0.100(4) 0.101(3) 0.122(4) 0.039(3) 0.067(3) 0.019(3) C60 0.098(4) 0.083(3) 0.100(4) 0.019(3) 0.026(3) 0.013(3) C61 0.126(6) 0.235(7) 0.240(8) 0.085(6) 0.113(6) 0.100(5) C63 0.282(10) 0.093(4) 0.141(5) 0.048(4) 0.122(6) 0.049(5) C74 0.292(12) 0.155(7) 0.413(15) 0.130(8) 0.285(12) 0.083(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 O1 C17 1.306(3) . ? O2 C11 1.295(4) . ? N3 C21 1.307(4) . ? N3 C14 1.409(4) . ? N3 H3 0.85(3) . ? O4 C34 1.351(4) . ? O4 H4 0.8200 . ? O5 C24 1.347(4) . ? O5 H5 0.8200 . ? N6 C18 1.315(4) . ? N6 C22 1.400(4) . ? N6 H6 0.93(4) . ? O7 C20 1.350(3) . ? O7 H7 0.8200 . ? N8 C12 1.325(4) . ? N8 C26 1.409(4) . ? N8 H8 0.91(4) . ? N9 C16 1.369(4) . ? N9 C47 1.462(4) . ? N9 C33 1.468(4) . ? O10 C27 1.300(4) . ? C11 C28 1.403(4) . ? C11 C13 1.440(4) . ? C12 C23 1.389(4) . ? C12 H12 0.9300 . ? C13 C21 1.387(4) . ? C13 C36 1.414(4) . ? C14 C40 1.375(4) . ? C14 C20 1.381(4) . ? C15 C32 1.387(4) . ? C15 C17 1.391(4) . ? C15 H15 0.9300 . ? C16 C30 1.390(4) . ? C16 C29 1.424(4) . ? C17 C25 1.432(4) . ? C18 C25 1.389(4) . ? C18 H18 0.9300 . ? C19 C29 1.353(4) . ? C19 C23 1.410(4) . ? C19 H19 0.9300 . ? C20 C37 1.380(4) . ? C21 H21 0.9300 . ? C22 C49 1.378(5) . ? C22 C34 1.390(5) . ? C23 C27 1.430(5) . ? C24 C39 1.380(4) . ? C24 C26 1.387(4) . ? C25 C48 1.417(4) . ? C26 C35 1.383(4) . ? C27 C30 1.401(4) . ? C28 C44 1.367(4) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? N31 C32 1.362(4) . ? N31 C38 1.464(5) . ? N31 C59 1.465(5) . ? C32 C43 1.427(5) . ? C33 C58 1.475(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C41 1.383(5) . ? C35 C42 1.376(5) . ? C35 H35 0.9300 . ? C36 C56 1.336(4) . ? C36 H36 0.9300 . ? C37 C52 1.369(5) . ? C37 H37 0.9300 . ? C38 C51 1.493(5) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C53 1.370(5) . ? C39 H39 0.9300 . ? C40 C46 1.381(5) . ? C40 H40 0.9300 . ? C41 C55 1.359(6) . ? C41 H41 0.9300 . ? C42 C53 1.381(5) . ? C42 H42 0.9300 . ? C43 C48 1.345(5) . ? C43 H43 0.9300 . ? C44 N45 1.356(4) . ? C44 C56 1.422(5) . ? N45 C54 1.457(5) . ? N45 C63 1.808(8) . ? C46 C52 1.364(5) . ? C46 H46 0.9300 . ? C47 C50 1.512(5) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48 0.9300 . ? C49 C57 1.379(6) . ? C49 H49 0.9300 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 H52 0.9300 . ? C53 H53 0.9300 . ? C54 C60 1.480(5) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 C57 1.368(6) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 C61 1.457(6) . ? C59 H59A 0.9700 . ? C59 H59B 0.9700 . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 0.9600 . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C63 C74 1.253(8) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C74 H74A 0.9600 . ? C74 H74B 0.9600 . ? C74 H74C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 N3 C14 125.9(3) . . ? C21 N3 H3 114(2) . . ? C14 N3 H3 120(2) . . ? C34 O4 H4 109.5 . . ? C24 O5 H5 109.5 . . ? C18 N6 C22 127.4(3) . . ? C18 N6 H6 116(2) . . ? C22 N6 H6 117(2) . . ? C20 O7 H7 109.5 . . ? C12 N8 C26 126.5(3) . . ? C12 N8 H8 116(2) . . ? C26 N8 H8 117(2) . . ? C16 N9 C47 122.0(3) . . ? C16 N9 C33 120.7(3) . . ? C47 N9 C33 116.9(3) . . ? O2 C11 C28 122.4(3) . . ? O2 C11 C13 120.4(3) . . ? C28 C11 C13 117.2(3) . . ? N8 C12 C23 125.0(3) . . ? N8 C12 H12 117.5 . . ? C23 C12 H12 117.5 . . ? C21 C13 C36 119.3(3) . . ? C21 C13 C11 122.5(3) . . ? C36 C13 C11 118.3(3) . . ? C40 C14 C20 119.9(3) . . ? C40 C14 N3 121.6(3) . . ? C20 C14 N3 118.6(3) . . ? C32 C15 C17 123.0(3) . . ? C32 C15 H15 118.5 . . ? C17 C15 H15 118.5 . . ? N9 C16 C30 122.6(3) . . ? N9 C16 C29 119.6(3) . . ? C30 C16 C29 117.7(3) . . ? O1 C17 C15 121.4(3) . . ? O1 C17 C25 120.2(3) . . ? C15 C17 C25 118.5(3) . . ? N6 C18 C25 125.1(3) . . ? N6 C18 H18 117.5 . . ? C25 C18 H18 117.5 . . ? C29 C19 C23 122.0(3) . . ? C29 C19 H19 119.0 . . ? C23 C19 H19 119.0 . . ? O7 C20 C37 123.5(3) . . ? O7 C20 C14 116.9(3) . . ? C37 C20 C14 119.6(3) . . ? N3 C21 C13 126.6(3) . . ? N3 C21 H21 116.7 . . ? C13 C21 H21 116.7 . . ? C49 C22 C34 119.2(3) . . ? C49 C22 N6 123.4(4) . . ? C34 C22 N6 117.2(3) . . ? C12 C23 C19 119.3(3) . . ? C12 C23 C27 122.3(3) . . ? C19 C23 C27 118.3(3) . . ? O5 C24 C39 123.2(3) . . ? O5 C24 C26 117.6(3) . . ? C39 C24 C26 119.1(3) . . ? C18 C25 C48 120.0(3) . . ? C18 C25 C17 122.3(3) . . ? C48 C25 C17 117.6(3) . . ? C35 C26 C24 120.1(3) . . ? C35 C26 N8 122.2(3) . . ? C24 C26 N8 117.7(3) . . ? O10 C27 C30 121.7(3) . . ? O10 C27 C23 119.9(3) . . ? C30 C27 C23 118.5(3) . . ? C44 C28 C11 123.0(3) . . ? C44 C28 H28 118.5 . . ? C11 C28 H28 118.5 . . ? C19 C29 C16 120.9(3) . . ? C19 C29 H29 119.6 . . ? C16 C29 H29 119.6 . . ? C16 C30 C27 122.5(3) . . ? C16 C30 H30 118.7 . . ? C27 C30 H30 118.7 . . ? C32 N31 C38 122.4(3) . . ? C32 N31 C59 122.3(4) . . ? C38 N31 C59 114.8(3) . . ? N31 C32 C15 121.1(3) . . ? N31 C32 C43 121.2(3) . . ? C15 C32 C43 117.7(3) . . ? N9 C33 C58 114.3(3) . . ? N9 C33 H33A 108.7 . . ? C58 C33 H33A 108.7 . . ? N9 C33 H33B 108.7 . . ? C58 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? O4 C34 C41 122.7(4) . . ? O4 C34 C22 117.1(3) . . ? C41 C34 C22 120.2(4) . . ? C42 C35 C26 120.7(3) . . ? C42 C35 H35 119.7 . . ? C26 C35 H35 119.7 . . ? C56 C36 C13 122.7(3) . . ? C56 C36 H36 118.7 . . ? C13 C36 H36 118.7 . . ? C52 C37 C20 119.8(3) . . ? C52 C37 H37 120.1 . . ? C20 C37 H37 120.1 . . ? N31 C38 C51 112.5(3) . . ? N31 C38 H38A 109.1 . . ? C51 C38 H38A 109.1 . . ? N31 C38 H38B 109.1 . . ? C51 C38 H38B 109.1 . . ? H38A C38 H38B 107.8 . . ? C53 C39 C24 120.2(3) . . ? C53 C39 H39 119.9 . . ? C24 C39 H39 119.9 . . ? C14 C40 C46 120.2(3) . . ? C14 C40 H40 119.9 . . ? C46 C40 H40 119.9 . . ? C55 C41 C34 119.8(4) . . ? C55 C41 H41 120.1 . . ? C34 C41 H41 120.1 . . ? C35 C42 C53 118.8(4) . . ? C35 C42 H42 120.6 . . ? C53 C42 H42 120.6 . . ? C48 C43 C32 120.3(3) . . ? C48 C43 H43 119.8 . . ? C32 C43 H43 119.8 . . ? N45 C44 C28 120.8(3) . . ? N45 C44 C56 120.3(3) . . ? C28 C44 C56 118.9(3) . . ? C44 N45 C54 124.0(3) . . ? C44 N45 C63 118.7(3) . . ? C54 N45 C63 113.1(3) . . ? C52 C46 C40 119.5(3) . . ? C52 C46 H46 120.3 . . ? C40 C46 H46 120.3 . . ? N9 C47 C50 114.9(3) . . ? N9 C47 H47A 108.6 . . ? C50 C47 H47A 108.6 . . ? N9 C47 H47B 108.6 . . ? C50 C47 H47B 108.6 . . ? H47A C47 H47B 107.5 . . ? C43 C48 C25 122.7(3) . . ? C43 C48 H48 118.7 . . ? C25 C48 H48 118.7 . . ? C22 C49 C57 119.8(4) . . ? C22 C49 H49 120.1 . . ? C57 C49 H49 120.1 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C38 C51 H51A 109.5 . . ? C38 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C38 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C46 C52 C37 121.0(3) . . ? C46 C52 H52 119.5 . . ? C37 C52 H52 119.5 . . ? C39 C53 C42 121.1(3) . . ? C39 C53 H53 119.4 . . ? C42 C53 H53 119.4 . . ? N45 C54 C60 111.8(4) . . ? N45 C54 H54A 109.3 . . ? C60 C54 H54A 109.3 . . ? N45 C54 H54B 109.3 . . ? C60 C54 H54B 109.3 . . ? H54A C54 H54B 107.9 . . ? C41 C55 C57 120.6(4) . . ? C41 C55 H55 119.7 . . ? C57 C55 H55 119.7 . . ? C36 C56 C44 119.9(3) . . ? C36 C56 H56 120.0 . . ? C44 C56 H56 120.0 . . ? C55 C57 C49 120.4(4) . . ? C55 C57 H57 119.8 . . ? C49 C57 H57 119.8 . . ? C33 C58 H58A 109.5 . . ? C33 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C33 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C61 C59 N31 111.6(4) . . ? C61 C59 H59A 109.3 . . ? N31 C59 H59A 109.3 . . ? C61 C59 H59B 109.3 . . ? N31 C59 H59B 109.3 . . ? H59A C59 H59B 108.0 . . ? C54 C60 H60A 109.5 . . ? C54 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C54 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C59 C61 H61A 109.5 . . ? C59 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C59 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? C74 C63 N45 84.6(7) . . ? C74 C63 H63A 114.6 . . ? N45 C63 H63A 114.5 . . ? C74 C63 H63B 114.6 . . ? N45 C63 H63B 114.6 . . ? H63A C63 H63B 111.7 . . ? C63 C74 H74A 109.5 . . ? C63 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C63 C74 H74C 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.32 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.329 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 943713' ####################################################################### # # 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_sa1+cl _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety '2(C17 H20 N2 O2), 2(Cl), 2(H2 O)' _chemical_formula_sum 'C17 H23 Cl N2 O3' _chemical_melting_point ? _exptl_crystal_description rectangular _exptl_crystal_colour yellow _diffrn_ambient_temperature 293(2) _chemical_formula_weight 338.14 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' Al Al 0.0645 0.0514 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? 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 18.242(5) _cell_length_b 11.925(5) _cell_length_c 17.097(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 108.114(5) _cell_angle_gamma 90.000(5) _cell_volume 3535(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 924 _cell_measurement_theta_min 2.9529 _cell_measurement_theta_max 29.0664 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83830 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8031 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.1311 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 29.12 _reflns_number_total 4002 _reflns_number_gt 1713 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _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^)+(0.0218P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4002 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1826 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 O2 O 0.61774(13) 0.76392(18) 0.38737(11) 0.0472(6) Uani 1 1 d . . . H2 H 0.5895 0.8137 0.3945 0.071 Uiso 1 1 calc R . . N4 N 0.58136(15) 0.6191(2) 0.63410(14) 0.0433(7) Uani 1 1 d . . . O5 O 0.68979(15) 0.8083(2) 0.20909(13) 0.0689(8) Uani 1 1 d . . . H5 H 0.6676 0.8241 0.1608 0.103 Uiso 1 1 calc R . . N6 N 0.73527(14) 0.6823(2) 0.34097(13) 0.0392(7) Uani 1 1 d . . . H6 H 0.6991 0.7315 0.3308 0.047 Uiso 1 1 calc R . . C7 C 0.72547(18) 0.5562(3) 0.53305(18) 0.0440(9) Uani 1 1 d . . . H7 H 0.7684 0.5102 0.5412 0.053 Uiso 1 1 calc R . . C8 C 0.62142(18) 0.6217(3) 0.57943(17) 0.0378(8) Uani 1 1 d . . . C9 C 0.63852(18) 0.6960(3) 0.45380(16) 0.0356(8) Uani 1 1 d . . . C10 C 0.70295(17) 0.6261(2) 0.46259(17) 0.0356(8) Uani 1 1 d . . . C11 C 0.77724(18) 0.6740(3) 0.28371(17) 0.0379(8) Uani 1 1 d . . . C12 C 0.7500(2) 0.7393(3) 0.21341(19) 0.0458(9) Uani 1 1 d . . . C13 C 0.59825(17) 0.6933(3) 0.50998(16) 0.0390(8) Uani 1 1 d . . . H13 H 0.5553 0.7391 0.5021 0.047 Uiso 1 1 calc R . . C14 C 0.74648(17) 0.6218(3) 0.40813(17) 0.0397(8) Uani 1 1 d . . . H14 H 0.7873 0.5713 0.4206 0.048 Uiso 1 1 calc R . . C15 C 0.6037(2) 0.5435(3) 0.70609(19) 0.0600(11) Uani 1 1 d . . . H15A H 0.5866 0.5758 0.7495 0.072 Uiso 1 1 calc R . . H15B H 0.6595 0.5381 0.7263 0.072 Uiso 1 1 calc R . . C16 C 0.87536(19) 0.5978(3) 0.2340(2) 0.0559(10) Uani 1 1 d . . . H16 H 0.9176 0.5509 0.2410 0.067 Uiso 1 1 calc R . . C17 C 0.8481(2) 0.6612(3) 0.1639(2) 0.0558(10) Uani 1 1 d . . . H17 H 0.8718 0.6562 0.1232 0.067 Uiso 1 1 calc R . . C18 C 0.50905(19) 0.6802(3) 0.61999(18) 0.0481(9) Uani 1 1 d . . . H18A H 0.5142 0.7536 0.5978 0.058 Uiso 1 1 calc R . . H18B H 0.4998 0.6913 0.6723 0.058 Uiso 1 1 calc R . . C19 C 0.68662(19) 0.5540(3) 0.58932(17) 0.0447(9) Uani 1 1 d . . . H19 H 0.7035 0.5070 0.6348 0.054 Uiso 1 1 calc R . . C20 C 0.83946(19) 0.6042(3) 0.29445(18) 0.0492(9) Uani 1 1 d . . . H20 H 0.8574 0.5613 0.3420 0.059 Uiso 1 1 calc R . . C21 C 0.4400(2) 0.6214(3) 0.5617(2) 0.0628(10) Uani 1 1 d . . . H21A H 0.4507 0.6032 0.5116 0.094 Uiso 1 1 calc R . . H21B H 0.3958 0.6698 0.5496 0.094 Uiso 1 1 calc R . . H21C H 0.4296 0.5537 0.5869 0.094 Uiso 1 1 calc R . . C22 C 0.7864(2) 0.7316(3) 0.15316(19) 0.0560(10) Uani 1 1 d . . . H22 H 0.7689 0.7743 0.1055 0.067 Uiso 1 1 calc R . . C23 C 0.5706(2) 0.4278(3) 0.6873(2) 0.0853(13) Uani 1 1 d . . . H23A H 0.5153 0.4324 0.6665 0.128 Uiso 1 1 calc R . . H23B H 0.5853 0.3835 0.7367 0.128 Uiso 1 1 calc R . . H23C H 0.5898 0.3934 0.6468 0.128 Uiso 1 1 calc R . . Cl1 Cl 0.61137(5) 0.89497(8) 0.03579(5) 0.0577(3) Uani 1 1 d . . . O1 O 0.52858(15) 0.9307(2) 0.39576(13) 0.0621(7) Uani 1 1 d G . . H1A H 0.5546 0.9732 0.4343 0.093 Uiso 1 1 d G . . H1B H 0.4863 0.9136 0.4039 0.093 Uiso 1 1 d G . . 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 O2 0.0517(17) 0.0521(16) 0.0452(13) 0.0120(12) 0.0259(11) 0.0156(13) N4 0.0448(19) 0.0523(19) 0.0384(15) 0.0045(15) 0.0211(13) 0.0014(16) O5 0.081(2) 0.0760(19) 0.0589(15) 0.0240(15) 0.0357(14) 0.0308(17) N6 0.0390(18) 0.0413(17) 0.0414(15) 0.0021(14) 0.0183(13) 0.0041(14) C7 0.037(2) 0.047(2) 0.0485(19) 0.0063(18) 0.0133(16) 0.0049(18) C8 0.038(2) 0.042(2) 0.0357(17) -0.0027(17) 0.0152(15) -0.0043(18) C9 0.040(2) 0.035(2) 0.0307(17) -0.0008(16) 0.0091(15) -0.0027(17) C10 0.034(2) 0.037(2) 0.0396(18) 0.0023(16) 0.0160(15) 0.0020(16) C11 0.044(2) 0.037(2) 0.0379(18) -0.0052(17) 0.0207(16) -0.0035(17) C12 0.057(3) 0.040(2) 0.046(2) 0.0021(18) 0.0230(18) 0.001(2) C13 0.038(2) 0.042(2) 0.0405(18) 0.0007(17) 0.0181(15) 0.0031(17) C14 0.035(2) 0.040(2) 0.0448(19) 0.0011(17) 0.0138(15) 0.0011(17) C15 0.065(3) 0.074(3) 0.049(2) 0.012(2) 0.0287(19) 0.008(2) C16 0.055(3) 0.056(2) 0.067(2) -0.001(2) 0.035(2) 0.003(2) C17 0.068(3) 0.057(3) 0.056(2) -0.007(2) 0.040(2) -0.010(2) C18 0.052(3) 0.053(2) 0.049(2) -0.0060(19) 0.0309(18) 0.000(2) C19 0.048(2) 0.051(2) 0.0362(18) 0.0102(17) 0.0146(16) 0.0009(19) C20 0.050(2) 0.054(2) 0.050(2) 0.0031(19) 0.0258(18) 0.001(2) C21 0.060(3) 0.052(2) 0.075(2) 0.001(2) 0.021(2) 0.002(2) C22 0.074(3) 0.055(3) 0.047(2) 0.0047(19) 0.031(2) -0.001(2) C23 0.077(3) 0.085(3) 0.089(3) 0.038(3) 0.019(2) 0.002(3) Cl1 0.0619(6) 0.0646(6) 0.0493(5) -0.0004(5) 0.0212(4) -0.0041(6) O1 0.0583(19) 0.0644(19) 0.0707(17) -0.0046(14) 0.0307(14) 0.0073(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 O2 C9 1.350(3) . ? O2 H2 0.8200 . ? N4 C8 1.354(3) . ? N4 C18 1.460(3) . ? N4 C15 1.477(4) . ? O5 C12 1.355(3) . ? O5 H5 0.8200 . ? N6 C14 1.317(3) . ? N6 C11 1.421(3) . ? N6 H6 0.8600 . ? C7 C19 1.361(4) . ? C7 C10 1.416(4) . ? C7 H7 0.9300 . ? C8 C19 1.404(4) . ? C8 C13 1.416(4) . ? C9 C13 1.379(3) . ? C9 C10 1.411(4) . ? C10 C14 1.400(4) . ? C11 C20 1.373(4) . ? C11 C12 1.388(4) . ? C12 C22 1.392(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C23 1.501(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.373(4) . ? C16 C20 1.386(4) . ? C16 H16 0.9300 . ? C17 C22 1.369(4) . ? C17 H17 0.9300 . ? C18 C21 1.515(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? O1 H1A 0.8499 . ? O1 H1B 0.8500 . ? 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 C9 O2 H2 109.5 . . ? C8 N4 C18 121.9(3) . . ? C8 N4 C15 121.4(3) . . ? C18 N4 C15 116.3(2) . . ? C12 O5 H5 109.5 . . ? C14 N6 C11 126.3(3) . . ? C14 N6 H6 116.9 . . ? C11 N6 H6 116.9 . . ? C19 C7 C10 122.4(3) . . ? C19 C7 H7 118.8 . . ? C10 C7 H7 118.8 . . ? N4 C8 C19 121.5(3) . . ? N4 C8 C13 120.6(3) . . ? C19 C8 C13 117.9(2) . . ? O2 C9 C13 122.0(3) . . ? O2 C9 C10 116.8(2) . . ? C13 C9 C10 121.2(3) . . ? C14 C10 C9 125.2(3) . . ? C14 C10 C7 118.0(3) . . ? C9 C10 C7 116.7(2) . . ? C20 C11 C12 121.0(3) . . ? C20 C11 N6 123.4(3) . . ? C12 C11 N6 115.6(3) . . ? O5 C12 C11 117.0(3) . . ? O5 C12 C22 124.4(3) . . ? C11 C12 C22 118.6(3) . . ? C9 C13 C8 120.9(3) . . ? C9 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? N6 C14 C10 126.4(3) . . ? N6 C14 H14 116.8 . . ? C10 C14 H14 116.8 . . ? N4 C15 C23 113.2(3) . . ? N4 C15 H15A 108.9 . . ? C23 C15 H15A 108.9 . . ? N4 C15 H15B 108.9 . . ? C23 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C20 119.6(3) . . ? C17 C16 H16 120.2 . . ? C20 C16 H16 120.2 . . ? C22 C17 C16 121.0(3) . . ? C22 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? N4 C18 C21 113.7(3) . . ? N4 C18 H18A 108.8 . . ? C21 C18 H18A 108.8 . . ? N4 C18 H18B 108.8 . . ? C21 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C7 C19 C8 120.7(3) . . ? C7 C19 H19 119.6 . . ? C8 C19 H19 119.6 . . ? C11 C20 C16 119.7(3) . . ? C11 C20 H20 120.1 . . ? C16 C20 H20 120.1 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 C12 120.2(3) . . ? C17 C22 H22 119.9 . . ? C12 C22 H22 119.9 . . ? C15 C23 H23A 109.5 . . ? C15 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C15 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? H1A O1 H1B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.187 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 959758' ####################################################################### # # 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_sa1-no3 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C17 H21 N3 O5' _chemical_formula_sum 'C17 H21 N3 O5' _chemical_melting_point ? _exptl_crystal_description rectangular _exptl_crystal_colour red _diffrn_ambient_temperature 293(2) _chemical_formula_weight 347.15 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/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1825(5) _cell_length_b 15.0467(11) _cell_length_c 14.7289(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.646(7) _cell_angle_gamma 90.00 _cell_volume 1769.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1392 _cell_measurement_theta_min 3.1353 _cell_measurement_theta_max 29.0023 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 763 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98287 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7799 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0616 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 29.07 _reflns_number_total 4010 _reflns_number_gt 2211 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. ; _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^)+(0.0415P)^2^+0.0403P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4010 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.37913(18) 0.03407(10) 0.59655(10) 0.0587(4) Uani 1 1 d . . . H1 H 0.4446 0.0136 0.6419 0.088 Uiso 1 1 calc R . . O2 O 0.3905(2) 0.27395(10) 0.56058(11) 0.0678(5) Uani 1 1 d . . . H2 H 0.4114 0.3197 0.5913 0.102 Uiso 1 1 calc R . . N2 N 0.28140(18) 0.14108(10) 0.45139(11) 0.0417(4) Uani 1 1 d . . . H2A H 0.3404 0.1355 0.5071 0.050 Uiso 1 1 calc R . . N1 N 0.18327(18) -0.26629(11) 0.57155(12) 0.0457(4) Uani 1 1 d . . . C12 C 0.2892(2) 0.22467(13) 0.40888(14) 0.0387(5) Uani 1 1 d . . . C8 C 0.1911(2) -0.01119(13) 0.45945(14) 0.0381(5) Uani 1 1 d . . . C7 C 0.0908(2) -0.07971(14) 0.41136(14) 0.0442(5) Uani 1 1 d . . . H7 H 0.0259 -0.0676 0.3525 0.053 Uiso 1 1 calc R . . C17 C 0.3463(2) 0.29467(14) 0.46922(15) 0.0447(5) Uani 1 1 d . . . C5 C 0.1833(2) -0.18393(13) 0.53587(14) 0.0387(5) Uani 1 1 d . . . C10 C 0.2825(2) -0.11556(14) 0.58622(14) 0.0425(5) Uani 1 1 d . . . H10 H 0.3461 -0.1274 0.6454 0.051 Uiso 1 1 calc R . . C11 C 0.1952(2) 0.07091(13) 0.41627(14) 0.0405(5) Uani 1 1 d . . . H11 H 0.1300 0.0766 0.3563 0.049 Uiso 1 1 calc R . . C13 C 0.2455(2) 0.23859(15) 0.31410(15) 0.0476(5) Uani 1 1 d . . . H13 H 0.2088 0.1914 0.2740 0.057 Uiso 1 1 calc R . . C16 C 0.3528(3) 0.37895(15) 0.43326(18) 0.0538(6) Uani 1 1 d . . . H16 H 0.3880 0.4265 0.4731 0.065 Uiso 1 1 calc R . . C9 C 0.2865(2) -0.03250(14) 0.54935(14) 0.0407(5) Uani 1 1 d . . . C2 C 0.0797(2) -0.33851(14) 0.52265(17) 0.0554(6) Uani 1 1 d . . . H2B H -0.0235 -0.3139 0.4861 0.066 Uiso 1 1 calc R . . H2C H 0.0507 -0.3789 0.5680 0.066 Uiso 1 1 calc R . . C14 C 0.2567(2) 0.32284(16) 0.27908(17) 0.0554(6) Uani 1 1 d . . . H14 H 0.2300 0.3325 0.2152 0.066 Uiso 1 1 calc R . . C6 C 0.0845(2) -0.16229(14) 0.44685(14) 0.0451(5) Uani 1 1 d . . . H6 H 0.0151 -0.2051 0.4127 0.054 Uiso 1 1 calc R . . C15 C 0.3075(2) 0.39283(16) 0.33918(18) 0.0570(6) Uani 1 1 d . . . H15 H 0.3111 0.4500 0.3156 0.068 Uiso 1 1 calc R . . C3 C 0.2950(2) -0.29077(15) 0.65954(16) 0.0549(6) Uani 1 1 d . . . H3A H 0.3998 -0.2589 0.6654 0.066 Uiso 1 1 calc R . . H3B H 0.3192 -0.3538 0.6586 0.066 Uiso 1 1 calc R . . C1 C 0.1683(3) -0.38950(17) 0.4593(2) 0.0794(8) Uani 1 1 d . . . H1A H 0.1938 -0.3501 0.4131 0.119 Uiso 1 1 calc R . . H1B H 0.0971 -0.4365 0.4294 0.119 Uiso 1 1 calc R . . H1C H 0.2702 -0.4143 0.4953 0.119 Uiso 1 1 calc R . . C4 C 0.2234(3) -0.2709(2) 0.74282(17) 0.0834(9) Uani 1 1 d . . . H4A H 0.1189 -0.3017 0.7373 0.125 Uiso 1 1 calc R . . H4B H 0.2050 -0.2081 0.7463 0.125 Uiso 1 1 calc R . . H4C H 0.3004 -0.2901 0.7982 0.125 Uiso 1 1 calc R . . O6 O 0.4887(2) 0.40731(11) 0.68671(12) 0.0714(5) Uani 1 1 d . . . N4 N 0.3622(3) 0.44867(13) 0.69668(14) 0.0559(5) Uani 1 1 d . . . O8 O 0.36977(19) 0.49824(12) 0.76514(11) 0.0695(5) Uani 1 1 d . . . O3 O 0.2302(2) 0.43968(15) 0.64105(14) 0.1140(8) 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 O1 0.0765(11) 0.0426(9) 0.0464(10) 0.0020(8) -0.0097(7) -0.0120(8) O2 0.1053(12) 0.0458(10) 0.0490(10) -0.0075(8) 0.0097(9) -0.0113(9) N2 0.0500(9) 0.0340(10) 0.0395(10) -0.0011(9) 0.0062(7) -0.0009(8) N1 0.0466(9) 0.0366(10) 0.0536(11) 0.0054(9) 0.0105(8) -0.0008(8) C12 0.0370(10) 0.0329(12) 0.0473(12) 0.0041(11) 0.0116(9) 0.0031(9) C8 0.0456(11) 0.0325(12) 0.0361(11) -0.0015(10) 0.0089(9) 0.0015(9) C7 0.0498(12) 0.0437(14) 0.0365(12) -0.0030(11) 0.0040(9) -0.0015(10) C17 0.0484(11) 0.0380(13) 0.0482(13) -0.0006(11) 0.0115(10) 0.0013(10) C5 0.0410(11) 0.0341(12) 0.0438(12) 0.0015(10) 0.0155(9) 0.0015(9) C10 0.0485(11) 0.0415(13) 0.0360(12) 0.0026(10) 0.0057(9) 0.0003(9) C11 0.0412(11) 0.0408(13) 0.0395(12) -0.0035(10) 0.0088(9) 0.0032(9) C13 0.0440(11) 0.0470(14) 0.0497(14) 0.0050(12) 0.0055(9) -0.0002(10) C16 0.0530(13) 0.0375(13) 0.0717(17) -0.0021(13) 0.0155(11) -0.0028(10) C9 0.0452(11) 0.0373(12) 0.0387(12) -0.0070(10) 0.0073(9) -0.0044(9) C2 0.0512(13) 0.0395(13) 0.0754(17) 0.0068(12) 0.0138(12) -0.0083(10) C14 0.0471(13) 0.0594(17) 0.0569(15) 0.0179(13) 0.0053(11) 0.0020(11) C6 0.0480(12) 0.0393(13) 0.0460(13) -0.0041(11) 0.0058(10) -0.0038(10) C15 0.0479(13) 0.0422(14) 0.0806(19) 0.0201(14) 0.0135(12) 0.0042(10) C3 0.0519(13) 0.0478(14) 0.0658(16) 0.0159(12) 0.0144(11) 0.0018(10) C1 0.0792(17) 0.0547(17) 0.104(2) -0.0213(16) 0.0199(16) 0.0004(13) C4 0.0828(17) 0.110(2) 0.0618(18) 0.0199(17) 0.0244(14) -0.0027(16) O6 0.0739(11) 0.0679(12) 0.0708(12) -0.0164(10) 0.0120(9) 0.0006(9) N4 0.0664(13) 0.0489(13) 0.0474(12) 0.0037(11) 0.0019(11) -0.0105(10) O8 0.0798(11) 0.0763(13) 0.0489(10) -0.0143(10) 0.0065(8) 0.0066(9) O3 0.0871(13) 0.130(2) 0.0990(16) -0.0382(14) -0.0367(12) 0.0099(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.353(2) . ? O1 H1 0.8200 . ? O2 C17 1.351(2) . ? O2 H2 0.8200 . ? N2 C11 1.312(2) . ? N2 C12 1.413(2) . ? N2 H2A 0.8600 . ? N1 C5 1.346(2) . ? N1 C3 1.460(2) . ? N1 C2 1.467(2) . ? C12 C13 1.379(3) . ? C12 C17 1.391(3) . ? C8 C11 1.393(3) . ? C8 C7 1.408(3) . ? C8 C9 1.419(3) . ? C7 C6 1.353(3) . ? C7 H7 0.9300 . ? C17 C16 1.380(3) . ? C5 C10 1.416(3) . ? C5 C6 1.419(3) . ? C10 C9 1.366(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C16 C15 1.370(3) . ? C16 H16 0.9300 . ? C2 C1 1.510(3) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C14 C15 1.380(3) . ? C14 H14 0.9300 . ? C6 H6 0.9300 . ? C15 H15 0.9300 . ? C3 C4 1.501(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? O6 N4 1.243(2) . ? N4 O3 1.212(2) . ? N4 O8 1.245(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1 109.5 . . ? C17 O2 H2 109.5 . . ? C11 N2 C12 127.91(17) . . ? C11 N2 H2A 116.0 . . ? C12 N2 H2A 116.0 . . ? C5 N1 C3 121.68(17) . . ? C5 N1 C2 122.68(17) . . ? C3 N1 C2 115.54(16) . . ? C13 C12 C17 120.53(19) . . ? C13 C12 N2 123.86(19) . . ? C17 C12 N2 115.62(18) . . ? C11 C8 C7 119.27(18) . . ? C11 C8 C9 124.28(18) . . ? C7 C8 C9 116.42(18) . . ? C6 C7 C8 123.02(19) . . ? C6 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? O2 C17 C16 124.7(2) . . ? O2 C17 C12 116.16(18) . . ? C16 C17 C12 119.1(2) . . ? N1 C5 C10 120.91(18) . . ? N1 C5 C6 121.54(18) . . ? C10 C5 C6 117.55(18) . . ? C9 C10 C5 121.17(18) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? N2 C11 C8 126.74(19) . . ? N2 C11 H11 116.6 . . ? C8 C11 H11 116.6 . . ? C14 C13 C12 119.6(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C16 C17 120.3(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? O1 C9 C10 122.19(18) . . ? O1 C9 C8 116.36(18) . . ? C10 C9 C8 121.45(18) . . ? N1 C2 C1 112.07(18) . . ? N1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? N1 C2 H2C 109.2 . . ? C1 C2 H2C 109.2 . . ? H2B C2 H2C 107.9 . . ? C13 C14 C15 119.8(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C7 C6 C5 120.36(19) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N1 C3 C4 113.24(18) . . ? N1 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N1 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O3 N4 O6 120.4(2) . . ? O3 N4 O8 119.6(2) . . ? O6 N4 O8 120.04(18) . . ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.191 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 959759'