# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ts #TrackingRef 'cis-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H33 N4 O2' _chemical_formula_weight 481.60 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3743(16) _cell_length_b 12.098(2) _cell_length_c 11.1576(18) _cell_angle_alpha 90.00 _cell_angle_beta 105.030(17) _cell_angle_gamma 90.00 _cell_volume 1352.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1871 _cell_measurement_theta_min 2.9178 _cell_measurement_theta_max 25.9596 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9851 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details 'SCALE3 ABSPACK' _exptl_special_details ; Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Xcalibur, Eos, Gemini' _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 5326 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3833 _reflns_number_gt 2339 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics OLEX2 _computing_publication_material OLEX2 _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^)+(0.0495P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(19) _refine_ls_number_reflns 3833 _refine_ls_number_parameters 348 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _refine_ls_shift/su_max 0.003 _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 N4 N 0.3040(3) 0.0963(3) 0.1256(3) 0.0381(8) Uani 1 1 d . . . C20 C 0.3050(3) 0.1790(3) 0.3345(3) 0.0450(10) Uani 1 1 d . . . N1 N 0.5550(3) 0.1735(3) 0.4021(3) 0.0496(9) Uani 1 1 d . . . N3 N 0.5750(3) 0.0002(3) 0.0260(3) 0.0348(7) Uani 1 1 d . . . N2 N 0.8272(3) 0.1090(3) 0.2734(3) 0.0390(8) Uani 1 1 d . . . C10 C 0.8250(3) 0.0007(3) 0.0797(3) 0.0391(9) Uani 1 1 d . . . O2 O 0.1928(2) -0.1682(2) -0.1444(2) 0.0556(7) Uani 1 1 d . . . C15 C 0.3266(3) -0.0115(3) -0.0610(3) 0.0347(8) Uani 1 1 d . . . C19 C 0.3080(3) 0.0824(3) 0.2494(3) 0.0398(9) Uani 1 1 d . . . C1 C 0.4402(3) 0.2353(3) 0.3645(3) 0.0409(9) Uani 1 1 d . . . C14 C 0.4648(3) 0.0252(3) -0.0688(3) 0.0329(8) Uani 1 1 d . . . C11 C 0.6895(3) 0.0299(3) -0.0044(3) 0.0345(8) Uani 1 1 d . . . C4 C 0.6664(4) 0.2392(4) 0.4282(3) 0.0463(10) Uani 1 1 d . . . C9 C 0.8222(3) 0.0091(3) 0.2147(3) 0.0374(8) Uani 1 1 d . . . C25 C 0.3054(3) -0.1353(3) -0.1011(3) 0.0381(9) Uani 1 1 d . . . C16 C 0.3182(3) -0.0036(3) 0.0712(3) 0.0333(8) Uani 1 1 d . . . C30 C 0.8550(3) -0.1217(3) 0.0608(3) 0.0448(10) Uani 1 1 d . . . C17 C 0.3315(3) -0.0822(3) 0.1618(3) 0.0479(10) Uani 1 1 d . . . H17 H 0.3433 -0.1576 0.1524 0.058 Uiso 1 1 calc R . . O1 O 0.7654(3) -0.1848(2) 0.0148(2) 0.0669(8) Uani 1 1 d . . . C13 C 0.5108(3) 0.0734(3) -0.1598(3) 0.0439(9) Uani 1 1 d . . . H13 H 0.4587 0.1001 -0.2349 0.053 Uiso 1 1 calc R . . C12 C 0.6515(3) 0.0757(3) -0.1201(3) 0.0447(9) Uani 1 1 d . . . H12 H 0.7084 0.1036 -0.1649 0.054 Uiso 1 1 calc R . . C5 C 0.8036(3) 0.1905(3) 0.4752(3) 0.0500(11) Uani 1 1 d . . . C26 C 0.4224(3) -0.2112(3) -0.0847(3) 0.0495(10) Uani 1 1 d . . . H26A H 0.3914 -0.2849 -0.1080 0.074 Uiso 1 1 calc R . . H26B H 0.4728 -0.2107 0.0007 0.074 Uiso 1 1 calc R . . H26C H 0.4781 -0.1869 -0.1361 0.074 Uiso 1 1 calc R . . C27 C 0.2196(3) 0.0562(3) -0.1501(3) 0.0479(10) Uani 1 1 d . . . H27A H 0.1330 0.0322 -0.1450 0.072 Uiso 1 1 calc R . . H27B H 0.2274 0.0462 -0.2333 0.072 Uiso 1 1 calc R . . H27C H 0.2311 0.1330 -0.1282 0.072 Uiso 1 1 calc R . . C6 C 0.8171(3) 0.0948(4) 0.3925(3) 0.0446(10) Uani 1 1 d . . . C3 C 0.6211(4) 0.3442(4) 0.4055(3) 0.0573(11) Uani 1 1 d . . . H3 H 0.6736 0.4074 0.4133 0.069 Uiso 1 1 calc R . . C23 C 0.9327(3) 0.0759(4) 0.0493(3) 0.0513(10) Uani 1 1 d . . . C2 C 0.4788(4) 0.3409(4) 0.3675(3) 0.0543(10) Uani 1 1 d . . . H2 H 0.4225 0.4018 0.3482 0.065 Uiso 1 1 calc R . . C22 C 0.9102(4) 0.2768(4) 0.4758(4) 0.0731(14) Uani 1 1 d . . . H22A H 0.9968 0.2452 0.5098 0.110 Uiso 1 1 calc R . . H22B H 0.8979 0.3387 0.5256 0.110 Uiso 1 1 calc R . . H22C H 0.9031 0.3012 0.3925 0.110 Uiso 1 1 calc R . . C18 C 0.3243(4) -0.0279(3) 0.2727(3) 0.0512(11) Uani 1 1 d . . . H18 H 0.3298 -0.0620 0.3486 0.061 Uiso 1 1 calc R . . C8 C 0.8098(4) -0.0703(3) 0.2968(4) 0.0550(11) Uani 1 1 d . . . H8 H 0.8040 -0.1461 0.2822 0.066 Uiso 1 1 calc R . . C29 C 0.2782(4) 0.1361(4) 0.4567(3) 0.0664(13) Uani 1 1 d . . . H29A H 0.1933 0.0993 0.4385 0.100 Uiso 1 1 calc R . . H29B H 0.2775 0.1972 0.5114 0.100 Uiso 1 1 calc R . . H29C H 0.3472 0.0851 0.4959 0.100 Uiso 1 1 calc R . . C24 C 0.9956(4) -0.1611(4) 0.1002(4) 0.0832(15) Uani 1 1 d . . . H24A H 0.9967 -0.2401 0.1085 0.125 Uiso 1 1 calc R . . H24B H 1.0395 -0.1282 0.1785 0.125 Uiso 1 1 calc R . . H24C H 1.0414 -0.1403 0.0390 0.125 Uiso 1 1 calc R . . C28 C 0.1966(3) 0.2631(4) 0.2766(4) 0.0622(12) Uani 1 1 d . . . H28A H 0.2104 0.2893 0.1997 0.093 Uiso 1 1 calc R . . H28B H 0.2008 0.3242 0.3324 0.093 Uiso 1 1 calc R . . H28C H 0.1105 0.2286 0.2614 0.093 Uiso 1 1 calc R . . C7 C 0.8074(4) -0.0164(4) 0.4092(3) 0.0633(12) Uani 1 1 d . . . H7 H 0.8004 -0.0509 0.4817 0.076 Uiso 1 1 calc R . . C21 C 0.8198(4) 0.1486(4) 0.6085(3) 0.0846(16) Uani 1 1 d . . . H21A H 0.7482 0.0988 0.6101 0.127 Uiso 1 1 calc R . . H21B H 0.8178 0.2102 0.6623 0.127 Uiso 1 1 calc R . . H21C H 0.9035 0.1106 0.6364 0.127 Uiso 1 1 calc R . . H2A H 0.823(4) 0.174(4) 0.242(3) 0.058(14) Uiso 1 1 d . . . H3A H 0.583(4) -0.021(4) 0.098(4) 0.074(15) Uiso 1 1 d . . . H1A H 0.563(4) 0.102(4) 0.397(3) 0.066(14) Uiso 1 1 d . . . H4A H 0.282(3) 0.155(3) 0.078(3) 0.047(11) 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 N4 0.0402(16) 0.033(2) 0.0423(18) -0.0001(17) 0.0128(14) 0.0029(16) C20 0.047(2) 0.048(3) 0.044(2) -0.0066(19) 0.0182(18) -0.001(2) N1 0.059(2) 0.038(2) 0.051(2) -0.0059(18) 0.0139(16) -0.003(2) N3 0.0402(17) 0.0323(19) 0.0339(16) 0.0003(15) 0.0129(14) -0.0009(15) N2 0.0414(16) 0.035(2) 0.0398(18) -0.0007(17) 0.0087(13) 0.0019(16) C10 0.0431(19) 0.032(2) 0.044(2) -0.0062(18) 0.0147(16) 0.0016(19) O2 0.0428(14) 0.0443(18) 0.0754(17) -0.0153(15) 0.0073(13) -0.0057(13) C15 0.0364(18) 0.032(2) 0.0354(18) -0.0010(17) 0.0090(15) 0.0021(17) C19 0.0386(18) 0.040(3) 0.043(2) 0.0020(19) 0.0149(16) -0.0032(18) C1 0.048(2) 0.034(2) 0.042(2) -0.0036(18) 0.0135(17) 0.002(2) C14 0.0431(19) 0.025(2) 0.0296(17) -0.0013(16) 0.0076(15) -0.0012(17) C11 0.0375(18) 0.031(2) 0.0396(19) -0.0030(17) 0.0180(15) -0.0009(17) C4 0.054(2) 0.047(3) 0.040(2) -0.012(2) 0.0169(18) -0.010(2) C9 0.0363(18) 0.034(2) 0.0410(19) -0.0046(18) 0.0079(15) 0.0013(18) C25 0.040(2) 0.038(3) 0.0363(19) 0.0004(17) 0.0102(16) -0.0024(18) C16 0.0281(16) 0.033(2) 0.0400(18) -0.0027(18) 0.0117(14) -0.0048(17) C30 0.046(2) 0.042(3) 0.049(2) -0.008(2) 0.0159(18) -0.005(2) C17 0.062(2) 0.031(2) 0.054(2) 0.0004(19) 0.020(2) 0.002(2) O1 0.0663(18) 0.043(2) 0.0858(19) -0.0119(16) 0.0095(15) -0.0001(16) C13 0.057(2) 0.041(3) 0.0318(18) 0.0059(18) 0.0073(17) -0.002(2) C12 0.052(2) 0.046(3) 0.042(2) 0.0038(19) 0.0224(17) -0.008(2) C5 0.050(2) 0.060(3) 0.036(2) -0.014(2) 0.0051(17) -0.006(2) C26 0.051(2) 0.033(2) 0.064(2) -0.002(2) 0.0154(17) 0.001(2) C27 0.046(2) 0.044(3) 0.049(2) 0.0024(19) 0.0052(17) 0.0039(19) C6 0.0365(18) 0.058(3) 0.037(2) 0.003(2) 0.0055(16) 0.005(2) C3 0.072(3) 0.043(3) 0.064(2) -0.015(2) 0.029(2) -0.013(2) C23 0.0430(19) 0.053(3) 0.064(2) -0.002(2) 0.0246(17) -0.020(2) C2 0.064(3) 0.040(3) 0.064(2) -0.001(2) 0.0256(19) 0.004(2) C22 0.056(2) 0.086(4) 0.077(3) -0.032(3) 0.015(2) -0.019(3) C18 0.064(3) 0.050(3) 0.042(2) 0.006(2) 0.0182(19) 0.001(2) C8 0.078(3) 0.031(3) 0.059(3) 0.009(2) 0.023(2) 0.007(2) C29 0.087(3) 0.064(3) 0.060(3) -0.006(2) 0.041(2) -0.003(2) C24 0.058(3) 0.057(3) 0.134(4) -0.020(3) 0.024(3) 0.015(3) C28 0.055(2) 0.061(3) 0.072(3) -0.016(2) 0.018(2) 0.012(2) C7 0.093(3) 0.055(3) 0.046(2) 0.019(2) 0.026(2) 0.010(3) C21 0.090(3) 0.119(5) 0.037(2) -0.013(2) 0.003(2) 0.008(3) _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 N4 C16 1.377(4) . ? N4 C19 1.381(4) . ? N4 H4A 0.87(4) . ? C20 C19 1.511(5) . ? C20 C1 1.517(5) . ? C20 C28 1.530(5) . ? C20 C29 1.549(5) . ? N1 C4 1.370(5) . ? N1 C1 1.376(5) . ? N1 H1A 0.87(4) . ? N3 C11 1.365(4) . ? N3 C14 1.375(4) . ? N3 H3A 0.82(4) . ? N2 C9 1.370(4) . ? N2 C6 1.371(4) . ? N2 H2A 0.86(4) . ? C10 C11 1.516(4) . ? C10 C9 1.517(4) . ? C10 C30 1.539(5) . ? C10 C23 1.544(5) . ? O2 C25 1.210(4) . ? C15 C16 1.504(4) . ? C15 C27 1.522(4) . ? C15 C14 1.524(4) . ? C15 C25 1.562(5) . ? C19 C18 1.362(5) . ? C1 C2 1.336(5) . ? C14 C13 1.360(4) . ? C11 C12 1.365(4) . ? C4 C3 1.356(5) . ? C4 C5 1.504(5) . ? C9 C8 1.356(5) . ? C25 C26 1.495(5) . ? C16 C17 1.367(5) . ? C30 O1 1.209(4) . ? C30 C24 1.488(5) . ? C17 C18 1.420(5) . ? C17 H17 0.9300 . ? C13 C12 1.412(4) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C5 C6 1.509(5) . ? C5 C22 1.519(6) . ? C5 C21 1.539(5) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C6 C7 1.366(5) . ? C3 C2 1.427(5) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C18 H18 0.9300 . ? C8 C7 1.419(5) . ? C8 H8 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C7 H7 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C16 N4 C19 110.8(3) . . ? C16 N4 H4A 119(2) . . ? C19 N4 H4A 130(2) . . ? C19 C20 C1 108.5(3) . . ? C19 C20 C28 112.4(3) . . ? C1 C20 C28 109.3(3) . . ? C19 C20 C29 109.4(3) . . ? C1 C20 C29 108.8(3) . . ? C28 C20 C29 108.3(3) . . ? C4 N1 C1 111.5(4) . . ? C4 N1 H1A 120(3) . . ? C1 N1 H1A 128(3) . . ? C11 N3 C14 110.8(3) . . ? C11 N3 H3A 117(3) . . ? C14 N3 H3A 132(3) . . ? C9 N2 C6 110.5(4) . . ? C9 N2 H2A 128(3) . . ? C6 N2 H2A 121(3) . . ? C11 C10 C9 110.2(3) . . ? C11 C10 C30 109.1(3) . . ? C9 C10 C30 104.9(3) . . ? C11 C10 C23 109.5(3) . . ? C9 C10 C23 112.4(3) . . ? C30 C10 C23 110.7(3) . . ? C16 C15 C27 112.9(3) . . ? C16 C15 C14 109.4(2) . . ? C27 C15 C14 110.1(3) . . ? C16 C15 C25 107.6(3) . . ? C27 C15 C25 107.7(2) . . ? C14 C15 C25 109.1(3) . . ? C18 C19 N4 106.2(3) . . ? C18 C19 C20 131.2(3) . . ? N4 C19 C20 122.4(3) . . ? C2 C1 N1 106.3(3) . . ? C2 C1 C20 133.6(4) . . ? N1 C1 C20 120.1(3) . . ? C13 C14 N3 106.6(3) . . ? C13 C14 C15 133.2(3) . . ? N3 C14 C15 119.9(3) . . ? N3 C11 C12 106.6(3) . . ? N3 C11 C10 120.8(3) . . ? C12 C11 C10 132.4(3) . . ? C3 C4 N1 105.7(4) . . ? C3 C4 C5 133.1(4) . . ? N1 C4 C5 121.1(4) . . ? C8 C9 N2 107.5(3) . . ? C8 C9 C10 130.8(4) . . ? N2 C9 C10 121.7(3) . . ? O2 C25 C26 121.0(3) . . ? O2 C25 C15 118.7(3) . . ? C26 C25 C15 120.3(3) . . ? C17 C16 N4 106.6(3) . . ? C17 C16 C15 131.3(3) . . ? N4 C16 C15 121.8(3) . . ? O1 C30 C24 120.7(4) . . ? O1 C30 C10 120.3(3) . . ? C24 C30 C10 119.0(3) . . ? C16 C17 C18 107.7(3) . . ? C16 C17 H17 126.1 . . ? C18 C17 H17 126.1 . . ? C14 C13 C12 108.0(3) . . ? C14 C13 H13 126.0 . . ? C12 C13 H13 126.0 . . ? C11 C12 C13 108.1(3) . . ? C11 C12 H12 126.0 . . ? C13 C12 H12 126.0 . . ? C4 C5 C6 108.5(3) . . ? C4 C5 C22 110.7(4) . . ? C6 C5 C22 110.4(3) . . ? C4 C5 C21 108.8(3) . . ? C6 C5 C21 109.5(3) . . ? C22 C5 C21 109.0(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C15 C27 H27A 109.5 . . ? C15 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C15 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C7 C6 N2 106.4(4) . . ? C7 C6 C5 130.6(4) . . ? N2 C6 C5 122.6(4) . . ? C4 C3 C2 108.1(4) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? C1 C2 C3 108.3(4) . . ? C1 C2 H2 125.8 . . ? C3 C2 H2 125.8 . . ? C5 C22 H22A 109.5 . . ? C5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C18 C17 108.6(3) . . ? C19 C18 H18 125.7 . . ? C17 C18 H18 125.7 . . ? C9 C8 C7 107.3(4) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? C20 C29 H29A 109.5 . . ? C20 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C20 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C24 H24A 109.5 . . ? C30 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C30 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C28 H28A 109.5 . . ? C20 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C20 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C6 C7 C8 108.3(3) . . ? C6 C7 H7 125.9 . . ? C8 C7 H7 125.9 . . ? C5 C21 H21A 109.5 . . ? C5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.253 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 909033' ####################################################################### # # 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_san_s #TrackingRef 'compound-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 N2 O4' _chemical_formula_weight 306.36 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 8.37(2) _cell_length_b 10.24(3) _cell_length_c 10.52(3) _cell_angle_alpha 95.85(5) _cell_angle_beta 110.15(4) _cell_angle_gamma 112.75(4) _cell_volume 752(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2003 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9788 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4625 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.1744 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.89 _reflns_number_total 2670 _reflns_number_gt 1631 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.2000P)^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 2670 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2386 _refine_ls_R_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.3458 _refine_ls_wR_factor_gt 0.2831 _refine_ls_goodness_of_fit_ref 1.271 _refine_ls_restrained_S_all 1.271 _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 O3 O 0.3200(4) 0.3768(3) 0.0418(3) 0.0263(7) Uani 1 1 d . . . N1 N 0.7576(5) 0.9862(4) 0.8614(3) 0.0290(8) Uani 1 1 d . . . O1 O 0.4640(4) 0.7644(3) 0.8798(3) 0.0317(8) Uani 1 1 d . . . O4 O 0.2404(4) 0.5863(3) -0.0078(3) 0.0358(8) Uani 1 1 d . . . N2 N 0.6690(4) 0.5945(4) 0.2213(3) 0.0268(8) Uani 1 1 d . . . O2 O 0.2680(4) 0.9054(3) 0.8892(3) 0.0371(8) Uani 1 1 d . . . C12 C 0.5238(5) 0.5533(4) 0.2605(4) 0.0232(8) Uani 1 1 d . . . C4 C 0.5921(5) 0.9026(4) 0.7516(4) 0.0242(8) Uani 1 1 d . . . C7 C 0.3314(5) 0.9245(4) 0.8041(4) 0.0288(9) Uani 1 1 d . . . C11 C 0.5989(5) 0.6135(4) 0.3998(4) 0.0284(9) Uani 1 1 d . . . H11 H 0.5302 0.6046 0.4566 0.034 Uiso 1 1 calc R . . C2 C 0.8190(5) 0.9940(4) 0.6795(4) 0.0313(9) Uani 1 1 d . . . H2 H 0.8848 1.0153 0.6208 0.038 Uiso 1 1 calc R . . C15 C 0.2549(5) 0.5704(4) 0.1030(4) 0.0290(9) Uani 1 1 d . . . C5 C 0.4151(5) 0.8234(4) 0.7685(4) 0.0266(8) Uani 1 1 d . . . C1 C 0.8979(5) 1.0444(4) 0.8198(4) 0.0303(9) Uani 1 1 d . . . H1 H 1.0282 1.1089 0.8785 0.036 Uiso 1 1 calc R . . C3 C 0.6263(6) 0.9059(4) 0.6344(4) 0.0321(10) Uani 1 1 d . . . H3 H 0.5351 0.8571 0.5399 0.039 Uiso 1 1 calc R . . C13 C 0.3251(5) 0.4630(4) 0.1567(4) 0.0254(8) Uani 1 1 d . . . C9 C 0.8312(5) 0.6771(4) 0.3314(4) 0.0296(9) Uani 1 1 d . . . H9 H 0.9536 0.7200 0.3305 0.035 Uiso 1 1 calc R . . C16 C 0.2072(6) 0.6554(5) 0.1966(5) 0.0405(11) Uani 1 1 d . . . H16A H 0.2209 0.7479 0.1724 0.061 Uiso 1 1 calc R . . H16B H 0.2941 0.6768 0.2949 0.061 Uiso 1 1 calc R . . H16C H 0.0756 0.5971 0.1835 0.061 Uiso 1 1 calc R . . C14 C 0.2011(5) 0.3688(4) 0.2170(4) 0.0297(9) Uani 1 1 d . . . H14A H 0.0674 0.3261 0.1493 0.045 Uiso 1 1 calc R . . H14B H 0.2186 0.4285 0.3042 0.045 Uiso 1 1 calc R . . H14C H 0.2356 0.2896 0.2373 0.045 Uiso 1 1 calc R . . C10 C 0.7941(5) 0.6906(5) 0.4457(4) 0.0315(9) Uani 1 1 d . . . H10 H 0.8849 0.7430 0.5397 0.038 Uiso 1 1 calc R . . C8 C 0.3224(7) 1.0332(5) 0.7291(6) 0.0440(12) Uani 1 1 d . . . H8A H 0.2242 1.0599 0.7351 0.066 Uiso 1 1 calc R . . H8B H 0.2905 0.9928 0.6302 0.066 Uiso 1 1 calc R . . H8C H 0.4463 1.1208 0.7707 0.066 Uiso 1 1 calc R . . C6 C 0.2642(6) 0.7047(5) 0.6383(5) 0.0374(10) Uani 1 1 d . . . H6A H 0.3130 0.6379 0.6128 0.056 Uiso 1 1 calc R . . H6B H 0.2287 0.7487 0.5613 0.056 Uiso 1 1 calc R . . H6C H 0.1520 0.6495 0.6553 0.056 Uiso 1 1 calc R . . H2A H 0.662(9) 0.566(7) 0.122(6) 0.068(16) Uiso 1 1 d . . . H1B H 0.394(7) 0.750(5) 0.903(5) 0.032(12) Uiso 1 1 d . . . H2B H 0.371(7) 0.318(6) 0.069(6) 0.042(12) Uiso 1 1 d . . . H1A H 0.766(6) 1.004(4) 0.933(5) 0.022(10) 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 O3 0.0247(14) 0.0355(15) 0.0171(13) 0.0045(11) 0.0064(11) 0.0146(12) N1 0.0270(17) 0.043(2) 0.0200(16) 0.0078(14) 0.0105(14) 0.0188(16) O1 0.0278(15) 0.0435(18) 0.0348(16) 0.0180(13) 0.0184(13) 0.0201(14) O4 0.0312(16) 0.0484(18) 0.0305(16) 0.0207(13) 0.0107(14) 0.0202(15) N2 0.0199(15) 0.0357(17) 0.0233(16) 0.0063(13) 0.0100(14) 0.0108(14) O2 0.0288(15) 0.0497(19) 0.0324(16) 0.0041(14) 0.0154(14) 0.0166(15) C12 0.0207(18) 0.0296(18) 0.0196(17) 0.0064(14) 0.0087(15) 0.0114(16) C4 0.0204(17) 0.033(2) 0.0232(17) 0.0102(15) 0.0092(15) 0.0150(17) C7 0.0187(17) 0.034(2) 0.028(2) 0.0011(16) 0.0070(16) 0.0101(17) C11 0.0244(19) 0.040(2) 0.0205(17) 0.0078(16) 0.0099(16) 0.0143(18) C2 0.027(2) 0.041(2) 0.028(2) 0.0098(16) 0.0132(17) 0.0165(19) C15 0.0178(18) 0.034(2) 0.029(2) 0.0084(16) 0.0078(17) 0.0076(17) C5 0.0229(18) 0.034(2) 0.0263(18) 0.0108(15) 0.0090(16) 0.0164(17) C1 0.0216(18) 0.038(2) 0.032(2) 0.0085(17) 0.0095(17) 0.0157(17) C3 0.031(2) 0.039(2) 0.028(2) 0.0083(17) 0.0167(19) 0.0141(19) C13 0.0221(18) 0.0278(18) 0.0244(18) 0.0049(15) 0.0128(16) 0.0074(16) C9 0.0205(18) 0.035(2) 0.0260(19) 0.0036(15) 0.0068(16) 0.0098(17) C16 0.028(2) 0.050(3) 0.042(2) 0.004(2) 0.010(2) 0.021(2) C14 0.0232(18) 0.036(2) 0.0238(18) 0.0087(16) 0.0098(16) 0.0079(18) C10 0.025(2) 0.045(2) 0.0227(19) 0.0070(16) 0.0047(16) 0.019(2) C8 0.042(2) 0.051(3) 0.056(3) 0.023(2) 0.027(2) 0.030(2) C6 0.027(2) 0.037(2) 0.038(2) -0.0001(18) 0.010(2) 0.0108(19) _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 O3 C13 1.401(5) . ? O3 H2B 0.88(5) . ? N1 C4 1.329(6) . ? N1 C1 1.340(5) . ? N1 H1A 0.73(4) . ? O1 C5 1.382(5) . ? O1 H1B 0.68(4) . ? O4 C15 1.165(5) . ? N2 C9 1.315(6) . ? N2 C12 1.346(5) . ? N2 H2A 1.03(5) . ? O2 C7 1.185(5) . ? C12 C11 1.344(6) . ? C12 C13 1.472(6) . ? C4 C3 1.359(5) . ? C4 C5 1.473(6) . ? C7 C8 1.439(6) . ? C7 C5 1.538(5) . ? C11 C10 1.382(6) . ? C11 H11 0.9500 . ? C2 C1 1.338(7) . ? C2 C3 1.379(7) . ? C2 H2 0.9500 . ? C15 C16 1.500(5) . ? C15 C13 1.507(6) . ? C5 C6 1.494(7) . ? C1 H1 0.9500 . ? C3 H3 0.9500 . ? C13 C14 1.488(5) . ? C9 C10 1.348(6) . ? C9 H9 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C10 H10 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O3 H2B 111(3) . . ? C4 N1 C1 110.8(4) . . ? C4 N1 H1A 123(3) . . ? C1 N1 H1A 126(4) . . ? C5 O1 H1B 106(4) . . ? C9 N2 C12 110.0(4) . . ? C9 N2 H2A 122(4) . . ? C12 N2 H2A 128(4) . . ? C11 C12 N2 107.2(4) . . ? C11 C12 C13 131.5(3) . . ? N2 C12 C13 121.3(4) . . ? N1 C4 C3 107.2(4) . . ? N1 C4 C5 121.8(4) . . ? C3 C4 C5 131.0(4) . . ? O2 C7 C8 121.9(3) . . ? O2 C7 C5 118.3(4) . . ? C8 C7 C5 119.8(3) . . ? C12 C11 C10 107.6(3) . . ? C12 C11 H11 126.2 . . ? C10 C11 H11 126.2 . . ? C1 C2 C3 108.7(3) . . ? C1 C2 H2 125.7 . . ? C3 C2 H2 125.7 . . ? O4 C15 C16 121.9(4) . . ? O4 C15 C13 120.0(3) . . ? C16 C15 C13 118.1(4) . . ? O1 C5 C4 105.8(3) . . ? O1 C5 C6 110.6(4) . . ? C4 C5 C6 111.5(3) . . ? O1 C5 C7 108.4(3) . . ? C4 C5 C7 113.1(4) . . ? C6 C5 C7 107.4(4) . . ? C2 C1 N1 106.6(4) . . ? C2 C1 H1 126.7 . . ? N1 C1 H1 126.7 . . ? C4 C3 C2 106.6(4) . . ? C4 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? O3 C13 C12 109.9(3) . . ? O3 C13 C14 110.4(3) . . ? C12 C13 C14 113.1(4) . . ? O3 C13 C15 106.9(3) . . ? C12 C13 C15 105.7(4) . . ? C14 C13 C15 110.5(3) . . ? N2 C9 C10 108.4(4) . . ? N2 C9 H9 125.8 . . ? C10 C9 H9 125.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 C10 C11 106.8(4) . . ? C9 C10 H10 126.6 . . ? C11 C10 H10 126.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.824 _diffrn_reflns_theta_full 26.89 _diffrn_measured_fraction_theta_full 0.824 _refine_diff_density_max 0.579 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 909034' ####################################################################### # # 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_san_s2 #TrackingRef 'compound-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N3 O2' _chemical_formula_weight 337.41 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 8.4855(12) _cell_length_b 10.2487(12) _cell_length_c 11.0122(13) _cell_angle_alpha 87.534(10) _cell_angle_beta 76.273(11) _cell_angle_gamma 85.501(11) _cell_volume 927.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 806 _cell_measurement_theta_min 2.7172 _cell_measurement_theta_max 28.8798 _exptl_crystal_description bock _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9890 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details 'SCALE3 ABSPACK' _exptl_special_details ; Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Xcalibur, Eos, Gemini' _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 7211 _diffrn_reflns_av_R_equivalents 0.0970 _diffrn_reflns_av_sigmaI/netI 0.2528 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.94 _reflns_number_total 4200 _reflns_number_gt 1071 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics OLEX2 _computing_publication_material OLEX2 _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^)+(0.0394P)^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 4200 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3197 _refine_ls_R_factor_gt 0.0899 _refine_ls_wR_factor_ref 0.2119 _refine_ls_wR_factor_gt 0.1314 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 N2 N 0.3228(6) 0.2259(4) 0.8954(4) 0.0562(13) Uani 1 1 d . . . O1 O 0.4324(5) -0.0053(3) 1.1440(3) 0.0818(13) Uani 1 1 d . . . N1 N 0.4629(7) 0.2462(5) 1.2567(5) 0.0781(17) Uani 1 1 d . . . C9 C 0.2528(7) 0.2825(5) 0.8047(5) 0.0604(15) Uani 1 1 d . . . C4 C 0.4087(7) 0.2613(5) 1.1490(5) 0.0557(14) Uani 1 1 d . . . C16 C 0.3107(7) 0.0436(5) 1.1184(5) 0.0622(16) Uani 1 1 d . . . C6 C 0.2220(7) 0.2448(5) 1.0124(5) 0.0564(14) Uani 1 1 d . . . N3 N 0.5846(8) 0.3748(6) 0.6894(5) 0.0783(16) Uani 1 1 d . . . C5 C 0.2689(7) 0.1934(5) 1.1296(5) 0.0574(15) Uani 1 1 d . . . C10 C 0.3364(8) 0.2708(5) 0.6672(5) 0.0701(16) Uani 1 1 d . . . C11 C 0.5182(8) 0.2733(6) 0.6479(5) 0.0622(15) Uani 1 1 d . . . C3 C 0.5137(7) 0.3416(5) 1.0736(5) 0.0630(16) Uani 1 1 d . . . H3 H 0.5086 0.3697 0.9931 0.076 Uiso 1 1 calc R . . C18 C 0.2681(6) 0.3867(5) 0.5901(4) 0.0846(19) Uani 1 1 d . . . H18A H 0.2742 0.4685 0.6275 0.127 Uiso 1 1 calc R . . H18B H 0.1569 0.3747 0.5905 0.127 Uiso 1 1 calc R . . H18C H 0.3319 0.3873 0.5054 0.127 Uiso 1 1 calc R . . C8 C 0.1050(7) 0.3373(5) 0.8645(5) 0.0731(17) Uani 1 1 d . . . H8 H 0.0293 0.3825 0.8266 0.088 Uiso 1 1 calc R . . C12 C 0.6433(9) 0.1909(6) 0.5895(5) 0.086(2) Uani 1 1 d . . . H12 H 0.6349 0.1129 0.5522 0.103 Uiso 1 1 calc R . . O2 O 0.3089(8) 0.1368(5) 0.5064(4) 0.163(3) Uani 1 1 d . . . C17 C 0.1928(7) -0.0394(5) 1.0819(6) 0.102(2) Uani 1 1 d . . . H17A H 0.2446 -0.0831 1.0058 0.153 Uiso 1 1 calc R . . H17B H 0.1003 0.0149 1.0693 0.153 Uiso 1 1 calc R . . H17C H 0.1579 -0.1033 1.1471 0.153 Uiso 1 1 calc R . . C7 C 0.0870(7) 0.3139(5) 0.9928(5) 0.0731(17) Uani 1 1 d . . . H7 H -0.0032 0.3413 1.0548 0.088 Uiso 1 1 calc R . . C15 C 0.1215(6) 0.2135(5) 1.2432(4) 0.0819(19) Uani 1 1 d . . . H15A H 0.0988 0.3054 1.2586 0.123 Uiso 1 1 calc R . . H15B H 0.1466 0.1695 1.3157 0.123 Uiso 1 1 calc R . . H15C H 0.0281 0.1782 1.2255 0.123 Uiso 1 1 calc R . . C2 C 0.6304(8) 0.3751(6) 1.1358(6) 0.083(2) Uani 1 1 d . . . H2 H 0.7149 0.4290 1.1052 0.100 Uiso 1 1 calc R . . C19 C 0.3017(8) 0.1450(7) 0.6172(6) 0.090(2) Uani 1 1 d . . . C1 C 0.5963(8) 0.3144(6) 1.2476(7) 0.087(2) Uani 1 1 d . . . H1 H 0.6543 0.3181 1.3091 0.105 Uiso 1 1 calc R . . C20 C 0.2583(8) 0.0339(5) 0.7008(5) 0.111(3) Uani 1 1 d . . . H20A H 0.2327 -0.0359 0.6549 0.166 Uiso 1 1 calc R . . H20B H 0.1653 0.0590 0.7662 0.166 Uiso 1 1 calc R . . H20C H 0.3480 0.0048 0.7367 0.166 Uiso 1 1 calc R . . C14 C 0.7479(9) 0.3583(7) 0.6586(6) 0.098(2) Uani 1 1 d . . . H14 H 0.8200 0.4140 0.6769 0.117 Uiso 1 1 calc R . . C13 C 0.7872(9) 0.2449(8) 0.5956(6) 0.104(3) Uani 1 1 d . . . H13 H 0.8921 0.2093 0.5622 0.125 Uiso 1 1 calc R . . H2A H 0.420(6) 0.179(4) 0.887(4) 0.066(17) Uiso 1 1 d . . . H1A H 0.418(5) 0.209(4) 1.325(4) 0.041(15) Uiso 1 1 d . . . H3A H 0.521(7) 0.432(5) 0.725(5) 0.09(3) 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 N2 0.048(3) 0.056(3) 0.063(3) -0.015(2) -0.009(3) 0.001(2) O1 0.080(3) 0.063(3) 0.107(3) -0.012(2) -0.031(3) 0.006(2) N1 0.106(5) 0.065(4) 0.067(4) 0.008(3) -0.027(4) -0.015(3) C9 0.061(4) 0.060(4) 0.064(4) -0.021(3) -0.021(3) 0.000(3) C4 0.061(4) 0.046(3) 0.057(4) -0.003(3) -0.010(3) 0.003(3) C16 0.061(4) 0.061(4) 0.061(4) -0.002(3) -0.007(3) -0.005(3) C6 0.050(4) 0.051(3) 0.067(4) -0.013(3) -0.011(3) -0.001(3) N3 0.066(5) 0.073(4) 0.098(4) -0.012(3) -0.023(4) -0.002(4) C5 0.051(4) 0.053(3) 0.061(3) -0.007(3) 0.001(3) -0.001(3) C10 0.076(5) 0.065(4) 0.071(4) -0.017(3) -0.018(4) -0.011(3) C11 0.059(4) 0.070(4) 0.059(3) -0.013(3) -0.015(3) -0.008(4) C3 0.074(5) 0.054(4) 0.060(4) -0.010(3) -0.015(3) -0.003(3) C18 0.076(5) 0.110(5) 0.075(4) 0.012(3) -0.036(3) -0.006(4) C8 0.057(4) 0.077(4) 0.087(4) -0.012(3) -0.025(4) 0.012(3) C12 0.086(6) 0.086(5) 0.082(4) -0.025(3) -0.012(4) 0.011(4) O2 0.300(8) 0.138(4) 0.074(3) -0.010(3) -0.062(4) -0.097(4) C17 0.089(5) 0.079(5) 0.147(6) -0.001(4) -0.039(5) -0.027(4) C7 0.054(4) 0.085(4) 0.076(4) -0.018(3) -0.006(3) 0.007(3) C15 0.068(5) 0.099(5) 0.070(4) -0.013(3) 0.001(3) 0.000(3) C2 0.074(5) 0.075(4) 0.099(5) -0.014(4) -0.015(4) -0.006(4) C19 0.100(6) 0.100(5) 0.074(4) -0.020(4) -0.019(4) -0.021(4) C1 0.078(5) 0.062(4) 0.136(7) -0.027(4) -0.050(5) 0.000(4) C20 0.174(8) 0.071(4) 0.084(4) -0.014(3) -0.018(4) -0.025(4) C14 0.067(6) 0.117(6) 0.114(6) -0.001(5) -0.029(5) -0.009(5) C13 0.073(6) 0.137(7) 0.086(5) -0.013(4) 0.005(5) 0.023(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C9 1.366(6) . ? N2 C6 1.379(5) . ? N2 H2A 0.91(4) . ? O1 C16 1.201(6) . ? N1 C1 1.358(7) . ? N1 C4 1.370(6) . ? N1 H1A 0.85(3) . ? C9 C8 1.361(6) . ? C9 C10 1.518(6) . ? C4 C3 1.366(6) . ? C4 C5 1.484(7) . ? C16 C17 1.497(7) . ? C16 C5 1.551(6) . ? C6 C7 1.356(6) . ? C6 C5 1.501(6) . ? N3 C14 1.345(8) . ? N3 C11 1.365(7) . ? N3 H3A 0.81(5) . ? C5 C15 1.553(5) . ? C10 C19 1.499(7) . ? C10 C11 1.509(7) . ? C10 C18 1.583(6) . ? C11 C12 1.355(7) . ? C3 C2 1.401(7) . ? C3 H3 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C8 C7 1.397(6) . ? C8 H8 0.9300 . ? C12 C13 1.397(8) . ? C12 H12 0.9300 . ? O2 C19 1.213(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C7 H7 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C2 C1 1.334(7) . ? C2 H2 0.9300 . ? C19 C20 1.447(7) . ? C1 H1 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C14 C13 1.357(8) . ? C14 H14 0.9300 . ? C13 H13 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 C9 N2 C6 110.8(5) . . ? C9 N2 H2A 129(3) . . ? C6 N2 H2A 120(3) . . ? C1 N1 C4 110.4(5) . . ? C1 N1 H1A 121(3) . . ? C4 N1 H1A 128(3) . . ? C8 C9 N2 106.5(5) . . ? C8 C9 C10 132.3(6) . . ? N2 C9 C10 121.2(5) . . ? C3 C4 N1 104.8(6) . . ? C3 C4 C5 132.6(6) . . ? N1 C4 C5 122.5(5) . . ? O1 C16 C17 120.6(6) . . ? O1 C16 C5 120.3(6) . . ? C17 C16 C5 118.9(5) . . ? C7 C6 N2 105.7(5) . . ? C7 C6 C5 132.2(5) . . ? N2 C6 C5 122.2(5) . . ? C14 N3 C11 110.5(6) . . ? C14 N3 H3A 133(5) . . ? C11 N3 H3A 116(5) . . ? C4 C5 C6 110.3(4) . . ? C4 C5 C16 111.2(5) . . ? C6 C5 C16 108.6(4) . . ? C4 C5 C15 110.1(4) . . ? C6 C5 C15 109.7(4) . . ? C16 C5 C15 106.9(4) . . ? C19 C10 C11 108.1(5) . . ? C19 C10 C9 110.9(5) . . ? C11 C10 C9 110.7(5) . . ? C19 C10 C18 107.4(5) . . ? C11 C10 C18 110.4(4) . . ? C9 C10 C18 109.3(4) . . ? C12 C11 N3 107.0(6) . . ? C12 C11 C10 132.1(7) . . ? N3 C11 C10 120.9(6) . . ? C4 C3 C2 109.7(5) . . ? C4 C3 H3 125.1 . . ? C2 C3 H3 125.1 . . ? C10 C18 H18A 109.5 . . ? C10 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C10 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 C8 C7 108.0(5) . . ? C9 C8 H8 126.0 . . ? C7 C8 H8 126.0 . . ? C11 C12 C13 107.4(6) . . ? C11 C12 H12 126.3 . . ? C13 C12 H12 126.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 C7 C8 109.1(5) . . ? C6 C7 H7 125.5 . . ? C8 C7 H7 125.5 . . ? C5 C15 H15A 109.5 . . ? C5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 C2 C3 106.4(6) . . ? C1 C2 H2 126.8 . . ? C3 C2 H2 126.8 . . ? O2 C19 C20 119.9(6) . . ? O2 C19 C10 119.8(6) . . ? C20 C19 C10 120.3(6) . . ? C2 C1 N1 108.7(6) . . ? C2 C1 H1 125.7 . . ? N1 C1 H1 125.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C14 C13 106.9(7) . . ? N3 C14 H14 126.6 . . ? C13 C14 H14 126.6 . . ? C14 C13 C12 108.3(6) . . ? C14 C13 H13 125.9 . . ? C12 C13 H13 125.9 . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 28.94 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.269 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 909035'