data_7a # inserted by JOC editorial office # g # L0704 # CIF for cmpd 7a in Aizpurua, Palomo, Balentova et al. submitted to # J. Org. Chem. _audit_creation_method SHELXL-97 _audit_creation_date 07-02-13 _chemical_name_systematic ; 2-(2-{(3R)-benzyl-3-[2-(tert-butoxycarbonylamino)-(2R)-propanamido]- 2-oxoazetidin-1-yl}-2-methylpro panamido)-(2R)-propanamide ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C25 H37 N5 O6, C H4 O' _chemical_formula_sum 'C26 H41 N5 O7' _chemical_formula_weight 535.64 _chemical_melting_point 464 loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 52 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 82 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 10 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 14 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5901(3) _cell_length_b 10.9851(3) _cell_length_c 13.8555(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.0403(16) _cell_angle_gamma 90.00 _cell_volume 1451.55(7) _cell_formula_units_Z 2 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.0895 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: MeOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.467(2) Frames collected: 298 Seconds exposure per frame: 16 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 31840 _diffrn_reflns_av_R_equivalents 0.0940 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 3489 _reflns_number_gt 2672 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2006)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0644P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom & difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.072(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack & Bernardinelli (2000), Friedel pairs merged' _refine_ls_abs_structure_Flack -0.2(12) _chemical_absolute_configuration syn _refine_ls_number_reflns 3488 _refine_ls_number_parameters 373 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.266 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.057 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 0.22941(18) 0.98210(19) 0.61061(14) 0.0321(5) Uani 1 1 d . . . O6 O 0.30336(18) 0.70950(17) 0.70029(13) 0.0260(4) Uani 1 1 d . . . O9 O 0.66390(19) 0.8615(2) 0.82489(13) 0.0354(5) Uani 1 1 d . . . O12 O 0.76692(18) 0.78538(19) 0.57387(13) 0.0299(5) Uani 1 1 d . . . O14 O 0.1111(3) 0.8404(2) 0.35596(18) 0.0487(6) Uani 1 1 d . . . O15 O 0.2704(2) 0.98168(19) 0.32032(14) 0.0341(5) Uani 1 1 d . . . N1 N 0.1174(2) 1.0273(2) 0.42417(16) 0.0265(5) Uani 1 1 d . . . H1 H 0.160(3) 1.099(3) 0.435(2) 0.036(9) Uiso 1 1 d . . . N4 N 0.0335(2) 0.8838(2) 0.64637(15) 0.0239(5) Uani 1 1 d . . . H4 H -0.054(3) 0.858(3) 0.623(2) 0.027(7) Uiso 1 1 d . . . N7 N 0.2904(2) 0.8707(2) 0.81103(14) 0.0228(5) Uani 1 1 d . . . N10 N 0.5082(2) 0.9314(2) 0.70472(15) 0.0233(5) Uani 1 1 d . . . H10 H 0.422(3) 0.946(3) 0.6861(18) 0.017(7) Uiso 1 1 d . . . N13 N 0.5636(2) 0.7136(2) 0.61820(18) 0.0305(6) Uani 1 1 d . . . H131 H 0.600(4) 0.629(4) 0.620(2) 0.046(9) Uiso 1 1 d . . . H132 H 0.474(5) 0.724(5) 0.646(3) 0.085(14) Uiso 1 1 d . . . C2 C 0.0227(3) 0.9980(3) 0.49572(19) 0.0265(6) Uani 1 1 d . . . H2 H -0.0429 0.9324 0.4693 0.032 Uiso 1 1 calc R . . C3 C 0.1058(3) 0.9525(3) 0.58917(19) 0.0244(6) Uani 1 1 d . . . C5 C 0.0922(3) 0.8354(2) 0.73908(18) 0.0234(6) Uani 1 1 d . . . C6 C 0.2446(3) 0.7890(3) 0.74172(17) 0.0220(6) Uani 1 1 d . . . C8 C 0.4284(3) 0.8908(3) 0.86498(18) 0.0249(6) Uani 1 1 d . . . C9 C 0.5436(3) 0.8916(3) 0.79608(19) 0.0244(6) Uani 1 1 d . . . C11 C 0.6114(3) 0.9303(3) 0.63488(19) 0.0253(6) Uani 1 1 d . . . H11 H 0.6973 0.9732 0.6647 0.030 Uiso 1 1 calc R . . C12 C 0.6532(3) 0.8026(3) 0.60790(18) 0.0237(6) Uani 1 1 d . . . C14 C 0.1626(3) 0.9414(3) 0.3663(2) 0.0312(7) Uani 1 1 d . . . C16 C 0.3184(3) 0.9124(3) 0.2383(2) 0.0365(8) Uani 1 1 d . . . C17 C 0.2008(4) 0.9064(4) 0.1563(2) 0.0497(9) Uani 1 1 d . . . H171 H 0.1230 0.8585 0.1770 0.074 Uiso 1 1 calc R . . H172 H 0.2351 0.8678 0.0996 0.074 Uiso 1 1 calc R . . H173 H 0.1681 0.9889 0.1393 0.074 Uiso 1 1 calc R . . C18 C 0.4371(4) 0.9907(4) 0.2091(3) 0.0495(9) Uani 1 1 d . . . H181 H 0.4009 1.0715 0.1895 0.074 Uiso 1 1 calc R . . H182 H 0.4778 0.9525 0.1546 0.074 Uiso 1 1 calc R . . H183 H 0.5094 0.9989 0.2642 0.074 Uiso 1 1 calc R . . C19 C 0.3708(4) 0.7877(4) 0.2713(3) 0.0614(11) Uani 1 1 d . . . H191 H 0.4365 0.7958 0.3301 0.092 Uiso 1 1 calc R . . H192 H 0.4186 0.7496 0.2199 0.092 Uiso 1 1 calc R . . H193 H 0.2913 0.7371 0.2852 0.092 Uiso 1 1 calc R . . C20 C -0.0613(3) 1.1094(3) 0.5160(2) 0.0344(7) Uani 1 1 d . . . H201 H 0.0026 1.1767 0.5355 0.052 Uiso 1 1 calc R . . H202 H -0.1193 1.0917 0.5684 0.052 Uiso 1 1 calc R . . H203 H -0.1217 1.1322 0.4573 0.052 Uiso 1 1 calc R . . C21 C 0.1528(3) 0.9302(3) 0.81613(19) 0.0247(6) Uani 1 1 d . . . H211 H 0.1484 1.0155 0.7930 0.030 Uiso 1 1 calc R . . H212 H 0.1157 0.9224 0.8799 0.030 Uiso 1 1 calc R . . C22 C -0.0100(3) 0.7409(3) 0.77282(19) 0.0258(6) Uani 1 1 d . . . H221 H -0.1006 0.7817 0.7792 0.031 Uiso 1 1 calc R . . H222 H -0.0270 0.6780 0.7217 0.031 Uiso 1 1 calc R . . C23 C 0.0375(3) 0.6782(3) 0.86755(19) 0.0262(6) Uani 1 1 d . . . C24 C -0.0167(4) 0.7120(3) 0.9519(2) 0.0377(7) Uani 1 1 d . . . H24 H -0.0823 0.7769 0.9508 0.045 Uiso 1 1 calc R . . C25 C 0.0239(5) 0.6518(4) 1.0383(2) 0.0532(10) Uani 1 1 d . . . H25 H -0.0143 0.6755 1.0960 0.064 Uiso 1 1 calc R . . C26 C 0.1188(4) 0.5586(4) 1.0409(3) 0.0562(11) Uani 1 1 d . . . H26 H 0.1474 0.5183 1.1003 0.067 Uiso 1 1 calc R . . C27 C 0.1725(3) 0.5234(4) 0.9572(3) 0.0560(11) Uani 1 1 d . . . H27 H 0.2380 0.4583 0.9588 0.067 Uiso 1 1 calc R . . C28 C 0.1318(3) 0.5819(3) 0.8707(3) 0.0406(8) Uani 1 1 d . . . H28 H 0.1685 0.5563 0.8130 0.049 Uiso 1 1 calc R . . C29 C 0.4278(3) 1.0158(3) 0.9134(2) 0.0349(7) Uani 1 1 d . . . H291 H 0.4056 1.0784 0.8638 0.052 Uiso 1 1 calc R . . H292 H 0.5204 1.0321 0.9480 0.052 Uiso 1 1 calc R . . H293 H 0.3570 1.0170 0.9595 0.052 Uiso 1 1 calc R . . C30 C 0.4581(3) 0.7891(3) 0.9402(2) 0.0330(7) Uani 1 1 d . . . H301 H 0.3837 0.7875 0.9835 0.050 Uiso 1 1 calc R . . H302 H 0.5485 0.8041 0.9782 0.050 Uiso 1 1 calc R . . H303 H 0.4611 0.7106 0.9068 0.050 Uiso 1 1 calc R . . C31 C 0.5549(3) 1.0000(3) 0.5438(2) 0.0359(7) Uani 1 1 d . . . H311 H 0.4673 0.9624 0.5155 0.054 Uiso 1 1 calc R . . H312 H 0.6240 0.9977 0.4965 0.054 Uiso 1 1 calc R . . H313 H 0.5371 1.0848 0.5609 0.054 Uiso 1 1 calc R . . O1 O 0.1181(3) 0.2309(3) 0.7469(2) 0.0768(9) Uani 1 1 d . . . H111 H 0.0460 0.2609 0.7163 0.092 Uiso 1 1 calc R . . C32 C 0.2343(5) 0.2739(5) 0.7093(4) 0.0824(14) Uani 1 1 d . . . H321 H 0.2218 0.3606 0.6940 0.124 Uiso 1 1 calc R . . H322 H 0.2481 0.2289 0.6500 0.124 Uiso 1 1 calc R . . H323 H 0.3165 0.2632 0.7569 0.124 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0207(10) 0.0411(12) 0.0342(10) 0.0097(9) 0.0013(8) -0.0054(9) O6 0.0220(9) 0.0267(11) 0.0307(10) -0.0084(9) 0.0088(8) 0.0000(8) O9 0.0200(10) 0.0530(14) 0.0325(11) -0.0001(10) -0.0011(8) 0.0029(10) O12 0.0208(10) 0.0365(11) 0.0332(10) -0.0025(9) 0.0067(8) 0.0005(9) O14 0.0590(14) 0.0306(12) 0.0619(14) -0.0081(11) 0.0318(12) -0.0146(11) O15 0.0360(11) 0.0334(11) 0.0357(11) -0.0043(9) 0.0171(9) -0.0064(9) N1 0.0297(13) 0.0264(13) 0.0246(12) 0.0003(10) 0.0081(10) -0.0057(11) N4 0.0175(11) 0.0305(13) 0.0239(11) 0.0046(10) 0.0022(9) -0.0021(10) N7 0.0199(11) 0.0253(12) 0.0235(11) -0.0049(10) 0.0036(9) 0.0005(10) N10 0.0172(11) 0.0267(12) 0.0262(12) -0.0024(10) 0.0028(9) 0.0013(10) N13 0.0243(12) 0.0273(14) 0.0417(14) -0.0058(11) 0.0116(11) -0.0025(11) C2 0.0230(13) 0.0323(15) 0.0251(13) 0.0068(12) 0.0068(11) -0.0023(12) C3 0.0197(13) 0.0267(14) 0.0270(13) -0.0007(11) 0.0031(11) 0.0001(12) C5 0.0214(13) 0.0250(14) 0.0243(13) 0.0001(11) 0.0057(11) -0.0003(11) C6 0.0188(12) 0.0255(14) 0.0218(13) 0.0006(12) 0.0027(10) -0.0036(12) C8 0.0218(13) 0.0302(15) 0.0218(13) -0.0038(12) -0.0017(10) 0.0019(12) C9 0.0217(14) 0.0253(14) 0.0258(14) -0.0043(11) 0.0008(11) -0.0013(11) C11 0.0199(13) 0.0283(14) 0.0282(14) 0.0014(12) 0.0048(11) -0.0046(12) C12 0.0185(13) 0.0318(15) 0.0210(13) 0.0004(11) 0.0037(10) 0.0006(12) C14 0.0323(15) 0.0308(17) 0.0318(15) 0.0044(13) 0.0099(12) -0.0037(14) C16 0.0395(17) 0.0352(18) 0.0382(17) -0.0072(14) 0.0203(14) 0.0012(14) C17 0.048(2) 0.060(3) 0.0426(18) -0.0149(17) 0.0112(15) -0.0037(17) C18 0.048(2) 0.055(2) 0.051(2) -0.0109(17) 0.0284(16) -0.0083(18) C19 0.069(3) 0.044(2) 0.076(3) 0.002(2) 0.028(2) 0.013(2) C20 0.0301(15) 0.0410(18) 0.0332(16) 0.0093(13) 0.0083(13) 0.0080(14) C21 0.0228(13) 0.0260(14) 0.0260(13) -0.0021(12) 0.0054(11) 0.0032(12) C22 0.0191(13) 0.0314(15) 0.0276(14) 0.0034(12) 0.0048(11) -0.0026(12) C23 0.0225(14) 0.0261(15) 0.0298(14) 0.0051(12) 0.0012(11) -0.0045(12) C24 0.0518(19) 0.0286(16) 0.0347(16) 0.0039(14) 0.0142(14) -0.0071(15) C25 0.082(3) 0.051(2) 0.0272(17) 0.0054(15) 0.0065(17) -0.025(2) C26 0.055(2) 0.059(3) 0.051(2) 0.0292(19) -0.0155(19) -0.023(2) C27 0.0299(17) 0.049(2) 0.086(3) 0.037(2) -0.0064(18) -0.0052(16) C28 0.0304(17) 0.0367(18) 0.055(2) 0.0148(16) 0.0079(15) 0.0009(14) C29 0.0331(16) 0.0388(18) 0.0324(16) -0.0131(14) 0.0027(13) -0.0018(14) C30 0.0298(15) 0.0426(18) 0.0267(14) 0.0045(14) 0.0032(12) 0.0053(14) C31 0.0346(16) 0.0361(18) 0.0382(16) 0.0118(14) 0.0093(13) 0.0050(14) O1 0.080(2) 0.078(2) 0.074(2) 0.0256(17) 0.0136(16) 0.0171(19) C32 0.056(3) 0.082(3) 0.108(4) 0.006(3) 0.004(3) -0.004(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 O3 C3 1.235(3) . ? O6 C6 1.216(3) . ? O9 C9 1.226(3) . ? O12 C12 1.248(3) . ? O14 C14 1.216(4) . ? O15 C14 1.345(3) . ? O15 C16 1.481(3) . ? N1 C14 1.339(4) . ? N1 C2 1.450(3) . ? N1 H1 0.89(4) . ? N4 C3 1.339(4) . ? N4 C5 1.448(3) . ? N4 H4 0.91(3) . ? N7 C6 1.354(3) . ? N7 C8 1.467(3) . ? N7 C21 1.481(3) . ? N10 C9 1.349(3) . ? N10 C11 1.456(3) . ? N10 H10 0.85(3) . ? N13 C12 1.319(4) . ? N13 H131 1.00(4) . ? N13 H132 0.99(4) . ? C2 C20 1.508(4) . ? C2 C3 1.531(4) . ? C2 H2 1.0000 . ? C5 C22 1.535(4) . ? C5 C6 1.544(4) . ? C5 C21 1.559(4) . ? C8 C29 1.528(4) . ? C8 C30 1.534(4) . ? C8 C9 1.534(4) . ? C11 C12 1.516(4) . ? C11 C31 1.526(4) . ? C11 H11 1.0000 . ? C16 C19 1.513(5) . ? C16 C18 1.515(5) . ? C16 C17 1.516(5) . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C20 H201 0.9800 . ? C20 H202 0.9800 . ? C20 H203 0.9800 . ? C21 H211 0.9900 . ? C21 H212 0.9900 . ? C22 C23 1.509(4) . ? C22 H221 0.9900 . ? C22 H222 0.9900 . ? C23 C24 1.378(4) . ? C23 C28 1.389(4) . ? C24 C25 1.387(4) . ? C24 H24 0.9500 . ? C25 C26 1.368(6) . ? C25 H25 0.9500 . ? C26 C27 1.373(6) . ? C26 H26 0.9500 . ? C27 C28 1.379(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 H291 0.9800 . ? C29 H292 0.9800 . ? C29 H293 0.9800 . ? C30 H301 0.9800 . ? C30 H302 0.9800 . ? C30 H303 0.9800 . ? C31 H311 0.9800 . ? C31 H312 0.9800 . ? C31 H313 0.9800 . ? O1 C32 1.363(5) . ? O1 H111 0.8400 . ? C32 H321 0.9800 . ? C32 H322 0.9800 . ? C32 H323 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 C14 O15 C16 120.7(2) . . ? C14 N1 C2 121.2(2) . . ? C14 N1 H1 123(2) . . ? C2 N1 H1 113(2) . . ? C3 N4 C5 123.7(2) . . ? C3 N4 H4 118.9(18) . . ? C5 N4 H4 117.0(19) . . ? C6 N7 C8 132.0(2) . . ? C6 N7 C21 95.87(19) . . ? C8 N7 C21 132.1(2) . . ? C9 N10 C11 119.9(2) . . ? C9 N10 H10 119.0(18) . . ? C11 N10 H10 120.3(17) . . ? C12 N13 H131 118(2) . . ? C12 N13 H132 124(3) . . ? H131 N13 H132 115(4) . . ? N1 C2 C20 109.4(2) . . ? N1 C2 C3 110.1(2) . . ? C20 C2 C3 110.4(2) . . ? N1 C2 H2 109.0 . . ? C20 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? O3 C3 N4 123.3(2) . . ? O3 C3 C2 121.2(2) . . ? N4 C3 C2 115.4(2) . . ? N4 C5 C22 108.5(2) . . ? N4 C5 C6 114.9(2) . . ? C22 C5 C6 113.7(2) . . ? N4 C5 C21 116.4(2) . . ? C22 C5 C21 116.6(2) . . ? C6 C5 C21 85.47(19) . . ? O6 C6 N7 132.8(2) . . ? O6 C6 C5 135.3(2) . . ? N7 C6 C5 91.9(2) . . ? N7 C8 C29 108.3(2) . . ? N7 C8 C30 109.2(2) . . ? C29 C8 C30 111.4(2) . . ? N7 C8 C9 110.74(19) . . ? C29 C8 C9 107.8(2) . . ? C30 C8 C9 109.4(2) . . ? O9 C9 N10 121.9(2) . . ? O9 C9 C8 120.7(2) . . ? N10 C9 C8 117.3(2) . . ? N10 C11 C12 112.8(2) . . ? N10 C11 C31 109.7(2) . . ? C12 C11 C31 109.9(2) . . ? N10 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C31 C11 H11 108.1 . . ? O12 C12 N13 122.2(3) . . ? O12 C12 C11 119.9(2) . . ? N13 C12 C11 117.8(2) . . ? O14 C14 N1 124.1(3) . . ? O14 C14 O15 124.6(3) . . ? N1 C14 O15 111.4(3) . . ? O15 C16 C19 110.7(3) . . ? O15 C16 C18 102.5(2) . . ? C19 C16 C18 111.1(3) . . ? O15 C16 C17 109.3(2) . . ? C19 C16 C17 112.6(3) . . ? C18 C16 C17 110.2(3) . . ? C16 C17 H171 109.5 . . ? C16 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C16 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? C16 C18 H181 109.5 . . ? C16 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C16 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C16 C19 H191 109.5 . . ? C16 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C16 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? C2 C20 H201 109.5 . . ? C2 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C2 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? N7 C21 C5 86.69(19) . . ? N7 C21 H211 114.2 . . ? C5 C21 H211 114.2 . . ? N7 C21 H212 114.2 . . ? C5 C21 H212 114.2 . . ? H211 C21 H212 111.4 . . ? C23 C22 C5 115.4(2) . . ? C23 C22 H221 108.4 . . ? C5 C22 H221 108.4 . . ? C23 C22 H222 108.4 . . ? C5 C22 H222 108.4 . . ? H221 C22 H222 107.5 . . ? C24 C23 C28 118.7(3) . . ? C24 C23 C22 120.5(3) . . ? C28 C23 C22 120.7(3) . . ? C23 C24 C25 120.5(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 119.8(3) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 120.3(4) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 120.4(3) . . ? C27 C28 H28 119.8 . . ? C23 C28 H28 119.8 . . ? C8 C29 H291 109.5 . . ? C8 C29 H292 109.5 . . ? H291 C29 H292 109.5 . . ? C8 C29 H293 109.5 . . ? H291 C29 H293 109.5 . . ? H292 C29 H293 109.5 . . ? C8 C30 H301 109.5 . . ? C8 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C8 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C11 C31 H311 109.5 . . ? C11 C31 H312 109.5 . . ? H311 C31 H312 109.5 . . ? C11 C31 H313 109.5 . . ? H311 C31 H313 109.5 . . ? H312 C31 H313 109.5 . . ? C32 O1 H111 109.5 . . ? O1 C32 H321 109.5 . . ? O1 C32 H322 109.5 . . ? H321 C32 H322 109.5 . . ? O1 C32 H323 109.5 . . ? H321 C32 H323 109.5 . . ? H322 C32 H323 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N1 C2 C20 -153.8(3) . . . . ? C14 N1 C2 C3 84.8(3) . . . . ? C5 N4 C3 O3 -0.7(4) . . . . ? C5 N4 C3 C2 -178.0(2) . . . . ? N1 C2 C3 O3 25.2(4) . . . . ? C20 C2 C3 O3 -95.7(3) . . . . ? N1 C2 C3 N4 -157.4(2) . . . . ? C20 C2 C3 N4 81.7(3) . . . . ? C3 N4 C5 C22 -168.3(2) . . . . ? C3 N4 C5 C6 -39.7(3) . . . . ? C3 N4 C5 C21 57.9(3) . . . . ? C8 N7 C6 O6 -2.7(5) . . . . ? C21 N7 C6 O6 179.1(3) . . . . ? C8 N7 C6 C5 176.3(3) . . . . ? C21 N7 C6 C5 -2.0(2) . . . . ? N4 C5 C6 O6 -62.2(4) . . . . ? C22 C5 C6 O6 63.7(4) . . . . ? C21 C5 C6 O6 -179.2(3) . . . . ? N4 C5 C6 N7 118.9(2) . . . . ? C22 C5 C6 N7 -115.2(2) . . . . ? C21 C5 C6 N7 1.90(19) . . . . ? C6 N7 C8 C29 165.0(3) . . . . ? C21 N7 C8 C29 -17.4(4) . . . . ? C6 N7 C8 C30 -73.5(3) . . . . ? C21 N7 C8 C30 104.1(3) . . . . ? C6 N7 C8 C9 47.0(4) . . . . ? C21 N7 C8 C9 -135.3(3) . . . . ? C11 N10 C9 O9 5.0(4) . . . . ? C11 N10 C9 C8 -177.8(2) . . . . ? N7 C8 C9 O9 -152.4(3) . . . . ? C29 C8 C9 O9 89.3(3) . . . . ? C30 C8 C9 O9 -31.9(4) . . . . ? N7 C8 C9 N10 30.4(3) . . . . ? C29 C8 C9 N10 -87.9(3) . . . . ? C30 C8 C9 N10 150.9(2) . . . . ? C9 N10 C11 C12 67.2(3) . . . . ? C9 N10 C11 C31 -169.9(2) . . . . ? N10 C11 C12 O12 -158.3(2) . . . . ? C31 C11 C12 O12 78.9(3) . . . . ? N10 C11 C12 N13 24.3(3) . . . . ? C31 C11 C12 N13 -98.6(3) . . . . ? C2 N1 C14 O14 13.7(4) . . . . ? C2 N1 C14 O15 -167.1(2) . . . . ? C16 O15 C14 O14 11.6(4) . . . . ? C16 O15 C14 N1 -167.5(2) . . . . ? C14 O15 C16 C19 -62.2(4) . . . . ? C14 O15 C16 C18 179.2(3) . . . . ? C14 O15 C16 C17 62.3(3) . . . . ? C6 N7 C21 C5 2.0(2) . . . . ? C8 N7 C21 C5 -176.3(3) . . . . ? N4 C5 C21 N7 -117.3(2) . . . . ? C22 C5 C21 N7 112.6(2) . . . . ? C6 C5 C21 N7 -1.74(17) . . . . ? N4 C5 C22 C23 178.2(2) . . . . ? C6 C5 C22 C23 49.0(3) . . . . ? C21 C5 C22 C23 -48.1(3) . . . . ? C5 C22 C23 C24 102.5(3) . . . . ? C5 C22 C23 C28 -80.4(3) . . . . ? C28 C23 C24 C25 0.9(4) . . . . ? C22 C23 C24 C25 178.0(3) . . . . ? C23 C24 C25 C26 0.3(5) . . . . ? C24 C25 C26 C27 -0.9(5) . . . . ? C25 C26 C27 C28 0.3(5) . . . . ? C26 C27 C28 C23 0.9(5) . . . . ? C24 C23 C28 C27 -1.5(4) . . . . ? C22 C23 C28 C27 -178.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 O12 0.89(4) 2.17(4) 3.044(3) 166(3) 2_656 yes N4 H4 O12 0.91(3) 1.95(3) 2.859(3) 174(3) 1_455 yes N10 H10 O3 0.85(3) 2.07(3) 2.902(3) 167(2) . yes N13 H131 O15 1.00(4) 2.15(4) 3.076(3) 154(3) 2_646 yes N13 H132 O6 0.99(4) 1.87(4) 2.850(3) 168(5) . yes O1 H111 O14 0.84 1.93 2.766(4) 176 2_546 yes _iucr_refine_instructions_details ; TITL CPAJ116 (L0704) CELL 0.71073 9.5901 10.9851 13.8555 90.0000 96.0403 90.0000 ZERR 2 0.0003 0.0003 0.0004 0.0000 0.0016 0.0000 LATT -1 SYMM -X, .50+Y, -Z SFAC C H N O UNIT 52 82 10 14 MERG 2 TEMP -113 L.S. 4 BOND $H CONF ACTA OMIT -1 0 1 HTAB N1 O12_$1 HTAB N4 O12_$2 HTAB N10 O3 HTAB N13 O15_$3 HTAB N13 O6 HTAB O1 O14_$4 EQIV $1 1-x,y+0.5,1-z EQIV $2 x-1,y,z EQIV $3 1-x,y-0.5,1-z EQIV $4 -x,y-0.5,1-z FMAP 2 PLAN 10 WGHT 0.064400 EXTI 0.072105 FVAR 0.35725 O3 4 0.229413 0.982096 0.610609 11.00000 0.02073 0.04109 = 0.03421 0.00972 0.00127 -0.00539 O6 4 0.303362 0.709502 0.700291 11.00000 0.02202 0.02667 = 0.03066 -0.00840 0.00883 0.00001 O9 4 0.663905 0.861481 0.824889 11.00000 0.02000 0.05299 = 0.03251 -0.00008 -0.00107 0.00287 O12 4 0.766924 0.785382 0.573869 11.00000 0.02078 0.03650 = 0.03322 -0.00255 0.00671 0.00052 O14 4 0.111111 0.840410 0.355957 11.00000 0.05900 0.03057 = 0.06194 -0.00813 0.03178 -0.01463 O15 4 0.270370 0.981685 0.320324 11.00000 0.03595 0.03342 = 0.03570 -0.00428 0.01713 -0.00641 N1 3 0.117438 1.027271 0.424172 11.00000 0.02967 0.02644 = 0.02462 0.00029 0.00806 -0.00574 H1 2 0.159893 1.099249 0.434781 11.00000 0.03635 N4 3 0.033505 0.883839 0.646366 11.00000 0.01746 0.03049 = 0.02386 0.00458 0.00222 -0.00208 H4 2 -0.054162 0.858177 0.623390 11.00000 0.02703 N7 3 0.290384 0.870722 0.811034 11.00000 0.01990 0.02530 = 0.02352 -0.00487 0.00362 0.00050 N10 3 0.508150 0.931436 0.704718 11.00000 0.01720 0.02667 = 0.02618 -0.00239 0.00283 0.00133 H10 2 0.422237 0.945835 0.686116 11.00000 0.01738 N13 3 0.563609 0.713588 0.618200 11.00000 0.02435 0.02728 = 0.04170 -0.00581 0.01160 -0.00250 H131 2 0.600231 0.628552 0.619664 11.00000 0.04575 H132 2 0.473506 0.724340 0.646010 11.00000 0.08462 C2 1 0.022702 0.997987 0.495723 11.00000 0.02303 0.03226 = 0.02505 0.00681 0.00684 -0.00231 AFIX 13 H2 2 -0.042883 0.932394 0.469343 11.00000 -1.20000 AFIX 0 C3 1 0.105776 0.952506 0.589175 11.00000 0.01969 0.02675 = 0.02696 -0.00075 0.00313 0.00012 C5 1 0.092244 0.835413 0.739078 11.00000 0.02145 0.02502 = 0.02435 0.00007 0.00574 -0.00035 C6 1 0.244587 0.788996 0.741724 11.00000 0.01879 0.02547 = 0.02184 0.00058 0.00272 -0.00365 C8 1 0.428412 0.890839 0.864981 11.00000 0.02177 0.03024 = 0.02176 -0.00379 -0.00165 0.00188 C9 1 0.543640 0.891574 0.796077 11.00000 0.02169 0.02530 = 0.02578 -0.00426 0.00076 -0.00129 C11 1 0.611400 0.930251 0.634881 11.00000 0.01989 0.02825 = 0.02819 0.00137 0.00478 -0.00455 AFIX 13 H11 2 0.697327 0.973162 0.664667 11.00000 -1.20000 AFIX 0 C12 1 0.653169 0.802622 0.607902 11.00000 0.01852 0.03184 = 0.02102 0.00041 0.00373 0.00062 C14 1 0.162555 0.941353 0.366289 11.00000 0.03235 0.03078 = 0.03181 0.00438 0.00995 -0.00373 C16 1 0.318447 0.912442 0.238325 11.00000 0.03953 0.03517 = 0.03818 -0.00723 0.02030 0.00116 C17 1 0.200756 0.906369 0.156315 11.00000 0.04795 0.05979 = 0.04263 -0.01487 0.01118 -0.00372 AFIX 137 H171 2 0.123003 0.858469 0.177040 11.00000 -1.50000 H172 2 0.235125 0.867797 0.099591 11.00000 -1.50000 H173 2 0.168081 0.988917 0.139316 11.00000 -1.50000 AFIX 0 C18 1 0.437096 0.990738 0.209089 11.00000 0.04834 0.05451 = 0.05064 -0.01087 0.02844 -0.00826 AFIX 137 H181 2 0.400891 1.071458 0.189541 11.00000 -1.50000 H182 2 0.477758 0.952474 0.154613 11.00000 -1.50000 H183 2 0.509382 0.998925 0.264204 11.00000 -1.50000 AFIX 0 C19 1 0.370813 0.787745 0.271295 11.00000 0.06857 0.04433 = 0.07560 0.00205 0.02768 0.01289 AFIX 137 H191 2 0.436504 0.795785 0.330094 11.00000 -1.50000 H192 2 0.418600 0.749627 0.219935 11.00000 -1.50000 H193 2 0.291253 0.737051 0.285212 11.00000 -1.50000 AFIX 0 C20 1 -0.061275 1.109401 0.516009 11.00000 0.03015 0.04096 = 0.03315 0.00927 0.00828 0.00797 AFIX 137 H201 2 0.002603 1.176738 0.535474 11.00000 -1.50000 H202 2 -0.119336 1.091694 0.568424 11.00000 -1.50000 H203 2 -0.121676 1.132189 0.457316 11.00000 -1.50000 AFIX 0 C21 1 0.152790 0.930196 0.816132 11.00000 0.02276 0.02605 = 0.02598 -0.00214 0.00539 0.00324 AFIX 23 H211 2 0.148384 1.015501 0.792966 11.00000 -1.20000 H212 2 0.115687 0.922375 0.879873 11.00000 -1.20000 AFIX 0 C22 1 -0.010029 0.740876 0.772823 11.00000 0.01909 0.03139 = 0.02757 0.00337 0.00482 -0.00258 AFIX 23 H221 2 -0.100634 0.781683 0.779237 11.00000 -1.20000 H222 2 -0.026991 0.678042 0.721714 11.00000 -1.20000 AFIX 0 C23 1 0.037514 0.678240 0.867551 11.00000 0.02245 0.02608 = 0.02982 0.00511 0.00119 -0.00449 C24 1 -0.016659 0.711966 0.951882 11.00000 0.05176 0.02861 = 0.03474 0.00394 0.01420 -0.00708 AFIX 43 H24 2 -0.082261 0.776878 0.950789 11.00000 -1.20000 AFIX 0 C25 1 0.023910 0.651817 1.038348 11.00000 0.08190 0.05070 = 0.02721 0.00539 0.00649 -0.02505 AFIX 43 H25 2 -0.014348 0.675466 1.096027 11.00000 -1.20000 AFIX 0 C26 1 0.118784 0.558594 1.040852 11.00000 0.05491 0.05862 = 0.05050 0.02925 -0.01547 -0.02265 AFIX 43 H26 2 0.147423 0.518334 1.100328 11.00000 -1.20000 AFIX 0 C27 1 0.172523 0.523359 0.957157 11.00000 0.02988 0.04933 = 0.08612 0.03679 -0.00638 -0.00523 AFIX 43 H27 2 0.238043 0.458337 0.958802 11.00000 -1.20000 AFIX 0 C28 1 0.131813 0.581935 0.870725 11.00000 0.03040 0.03668 = 0.05529 0.01484 0.00788 0.00094 AFIX 43 H28 2 0.168486 0.556268 0.812982 11.00000 -1.20000 AFIX 0 C29 1 0.427775 1.015774 0.913438 11.00000 0.03314 0.03885 = 0.03244 -0.01314 0.00272 -0.00176 AFIX 137 H291 2 0.405576 1.078430 0.863846 11.00000 -1.50000 H292 2 0.520368 1.032055 0.948009 11.00000 -1.50000 H293 2 0.356973 1.016958 0.959534 11.00000 -1.50000 AFIX 0 C30 1 0.458133 0.789061 0.940189 11.00000 0.02981 0.04264 = 0.02671 0.00446 0.00321 0.00526 AFIX 137 H301 2 0.383723 0.787547 0.983535 11.00000 -1.50000 H302 2 0.548539 0.804055 0.978225 11.00000 -1.50000 H303 2 0.461120 0.710580 0.906838 11.00000 -1.50000 AFIX 0 C31 1 0.554860 1.000022 0.543797 11.00000 0.03464 0.03613 = 0.03820 0.01182 0.00932 0.00498 AFIX 137 H311 2 0.467277 0.962389 0.515549 11.00000 -1.50000 H312 2 0.623952 0.997693 0.496506 11.00000 -1.50000 H313 2 0.537054 1.084778 0.560860 11.00000 -1.50000 AFIX 0 O1 4 0.118136 0.230892 0.746913 11.00000 0.07976 0.07796 = 0.07389 0.02563 0.01364 0.01713 AFIX 147 H111 2 0.046016 0.260924 0.716277 11.00000 -1.20000 AFIX 0 C32 1 0.234298 0.273908 0.709319 11.00000 0.05608 0.08213 = 0.10799 0.00639 0.00421 -0.00434 AFIX 137 H321 2 0.221813 0.360578 0.694016 11.00000 -1.50000 H322 2 0.248103 0.228864 0.650016 11.00000 -1.50000 H323 2 0.316499 0.263210 0.756893 11.00000 -1.50000 HKLF 4 REM CPAJ116 (L0704) REM R1 = 0.0439 for 2672 Fo > 4sig(Fo) and 0.0703 for all 3488 data REM 373 parameters refined using 1 restraints END WGHT 0.0644 0.0000 REM Highest difference peak 0.266, deepest hole -0.266, 1-sigma level 0.057 Q1 1 0.4700 0.8572 0.7178 11.00000 0.05 0.27 Q2 1 0.1900 1.0167 0.9806 11.00000 0.05 0.23 Q3 1 0.4279 0.7720 0.7282 11.00000 0.05 0.22 Q4 1 0.4328 0.7204 0.7791 11.00000 0.05 0.21 Q5 1 0.7493 0.8340 0.7585 11.00000 0.05 0.21 Q6 1 -0.0933 0.9026 0.6798 11.00000 0.05 0.20 Q7 1 0.3108 0.8514 0.8304 11.00000 0.05 0.20 Q8 1 0.5253 0.7172 0.6623 11.00000 0.05 0.20 Q9 1 0.0694 1.0005 0.4747 11.00000 0.05 0.19 Q10 1 -0.0680 0.8041 0.6834 11.00000 0.05 0.19 ; # End of CIF ============================================================