# Electronic Supplementary Material (ESI) for Chemical Communications # 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_3a _database_code_depnum_ccdc_archive 'CCDC 916313' #TrackingRef '3a.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N O4' _chemical_formula_sum 'C16 H17 N O4' _chemical_formula_weight 287.30 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' _space_group_crystal_system orthorhombic _space_group_IT_number 18 _space_group_name_H-M_alt 'P 21 21 2' _space_group_name_Hall 'P 2 2ab' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 10.3329(10) _cell_length_b 19.6202(19) _cell_length_c 7.1804(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1455.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4795 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.61 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_F_000 608 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.170 _exptl_absorpt_coefficient_mu 0.095 _shelx_estimated_absorpt_T_min 0.937 _shelx_estimated_absorpt_T_max 0.984 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS v2009/1, Sheldrick, G.M., (2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17114 _diffrn_reflns_av_unetI/netI 0.0304 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.076 _diffrn_reflns_theta_max 30.513 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 4410 _reflns_number_gt 3804 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.734 _reflns_Friedel_fraction_max 0.981 _reflns_Friedel_fraction_full 1.000 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; ? ; _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^)+(0.0675P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1476 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.6(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 4410 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.68101(16) 0.69495(8) 0.3963(2) 0.0245(3) Uani 1 1 d . . . . . H1 H 0.591(2) 0.6966(11) 0.437(3) 0.029 Uiso 1 1 d . U . . . C2 C 0.70054(16) 0.66993(8) 0.1957(2) 0.0231(3) Uani 1 1 d . . . . . H2A H 0.7675(19) 0.6372(11) 0.191(3) 0.028 Uiso 1 1 d . U . . . C3 C 0.75866(15) 0.73238(9) 0.0906(2) 0.0243(3) Uani 1 1 d . . . . . H3 H 0.805(2) 0.7188(10) -0.018(3) 0.029 Uiso 1 1 d . U . . . C4 C 0.65653(15) 0.78368(8) 0.0352(2) 0.0253(3) Uani 1 1 d . . . . . O1 O 0.64093(13) 0.80169(7) -0.12638(17) 0.0331(3) Uani 1 1 d . . . . . C5 C 0.57270(18) 0.81037(10) 0.1909(3) 0.0294(4) Uani 1 1 d . . . . . H5A H 0.534(2) 0.8523(12) 0.151(3) 0.035 Uiso 1 1 d . U . . . H5B H 0.503(2) 0.7765(11) 0.209(3) 0.035 Uiso 1 1 d . U . . . C6 C 0.64812(17) 0.82148(9) 0.3739(2) 0.0270(3) Uani 1 1 d . . . . . H6A H 0.689(2) 0.8670(11) 0.369(3) 0.032 Uiso 1 1 d . U . . . H6B H 0.591(2) 0.8227(11) 0.483(3) 0.032 Uiso 1 1 d . U . . . C7 C 0.74992(15) 0.76609(8) 0.4082(2) 0.0234(3) Uani 1 1 d . . . . . O2 O 0.81770(13) 0.77705(7) 0.57636(17) 0.0308(3) Uani 1 1 d . . . . . H2 H 0.763(2) 0.7844(13) 0.661(4) 0.046 Uiso 1 1 d . U . . . C8 C 0.84433(16) 0.76412(9) 0.2437(2) 0.0262(3) Uani 1 1 d . . . . . H8A H 0.922(2) 0.7340(11) 0.270(3) 0.031 Uiso 1 1 d . U . . . H8B H 0.876(2) 0.8118(12) 0.211(3) 0.031 Uiso 1 1 d . U . . . N1 N 0.74299(18) 0.64776(8) 0.5359(2) 0.0374(4) Uani 1 1 d . . . . . O3 O 0.6862(3) 0.64078(9) 0.6833(2) 0.0676(6) Uani 1 1 d . . . . . O4 O 0.84749(16) 0.62182(8) 0.5007(2) 0.0484(4) Uani 1 1 d . . . . . C9 C 0.58685(17) 0.63541(8) 0.1059(3) 0.0263(3) Uani 1 1 d . . . . . H9 H 0.593(2) 0.6295(10) -0.018(3) 0.032 Uiso 1 1 d . U . . . C10 C 0.48719(17) 0.60781(9) 0.1943(3) 0.0283(4) Uani 1 1 d . . . . . H10 H 0.482(2) 0.6118(11) 0.321(4) 0.034 Uiso 1 1 d . U . . . C11 C 0.38010(16) 0.56865(8) 0.1112(3) 0.0321(4) Uani 1 1 d . . . . . C12 C 0.3751(2) 0.55292(9) -0.0796(3) 0.0380(5) Uani 1 1 d . . . . . H12 H 0.448(3) 0.5686(13) -0.161(4) 0.046 Uiso 1 1 d . U . . . C13 C 0.2727(2) 0.51428(10) -0.1501(4) 0.0533(7) Uani 1 1 d . . . . . H13A H 0.2697 0.5039 -0.2793 0.064 Uiso 1 1 calc R U . . . C14 C 0.1760(2) 0.49101(11) -0.0342(5) 0.0622(8) Uani 1 1 d . . . . . H14 H 0.106(3) 0.4647(16) -0.089(5) 0.075 Uiso 1 1 d . U . . . C15 C 0.1798(2) 0.50631(11) 0.1536(5) 0.0598(8) Uani 1 1 d . . . . . H15 H 0.120(3) 0.493(2) 0.236(5) 0.072 Uiso 1 1 d . U . . . C16 C 0.2814(2) 0.54497(10) 0.2264(4) 0.0448(6) Uani 1 1 d . . . . . H16 H 0.281(3) 0.5595(14) 0.361(4) 0.054 Uiso 1 1 d . U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0254(7) 0.0263(7) 0.0218(7) 0.0011(6) 0.0013(6) -0.0025(6) C2 0.0221(7) 0.0253(7) 0.0218(7) -0.0001(6) 0.0032(6) -0.0015(6) C3 0.0216(7) 0.0304(8) 0.0209(7) 0.0002(6) 0.0037(6) -0.0022(6) C4 0.0244(7) 0.0268(7) 0.0249(7) 0.0013(6) -0.0016(6) -0.0050(6) O1 0.0382(7) 0.0363(7) 0.0250(6) 0.0044(5) -0.0050(5) -0.0058(5) C5 0.0263(8) 0.0333(9) 0.0286(8) 0.0019(7) -0.0019(7) 0.0036(7) C6 0.0285(8) 0.0279(8) 0.0246(8) -0.0024(6) 0.0010(7) -0.0001(6) C7 0.0236(7) 0.0254(7) 0.0212(7) -0.0003(6) -0.0008(6) -0.0035(6) O2 0.0312(6) 0.0370(7) 0.0243(6) -0.0026(5) -0.0061(5) -0.0037(5) C8 0.0205(7) 0.0315(8) 0.0267(8) 0.0019(6) 0.0019(6) -0.0048(6) N1 0.0587(11) 0.0278(7) 0.0256(7) 0.0018(6) -0.0045(8) -0.0038(7) O3 0.1172(16) 0.0541(10) 0.0313(8) 0.0176(7) 0.0185(10) 0.0107(11) O4 0.0530(9) 0.0450(8) 0.0473(9) 0.0042(7) -0.0177(7) 0.0086(7) C9 0.0269(8) 0.0279(8) 0.0241(8) -0.0031(6) -0.0005(6) -0.0034(6) C10 0.0267(8) 0.0276(8) 0.0307(9) -0.0040(7) 0.0000(7) -0.0021(6) C11 0.0235(8) 0.0207(7) 0.0521(11) -0.0015(7) -0.0025(8) 0.0010(6) C12 0.0375(10) 0.0222(8) 0.0543(13) -0.0006(8) -0.0154(9) 0.0013(7) C13 0.0544(14) 0.0256(9) 0.0799(17) -0.0033(10) -0.0380(13) 0.0002(9) C14 0.0345(11) 0.0288(10) 0.123(3) -0.0030(13) -0.0317(14) -0.0026(9) C15 0.0247(10) 0.0316(10) 0.123(3) 0.0035(14) 0.0020(13) -0.0024(8) C16 0.0263(9) 0.0302(9) 0.0779(17) -0.0014(10) 0.0084(10) 0.0005(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 C1 N1 1.507(2) . ? C1 C2 1.535(2) . ? C1 C7 1.569(2) . ? C1 H1 0.98(2) . ? C2 C9 1.501(2) . ? C2 C3 1.559(2) . ? C2 H2A 0.95(2) . ? C3 C4 1.512(2) . ? C3 C8 1.543(2) . ? C3 H3 0.95(2) . ? C4 O1 1.223(2) . ? C4 C5 1.508(3) . ? C5 C6 1.543(2) . ? C5 H5A 0.96(2) . ? C5 H5B 0.99(2) . ? C6 C7 1.532(2) . ? C6 H6A 0.99(2) . ? C6 H6B 0.98(2) . ? C7 O2 1.4126(19) . ? C7 C8 1.532(2) . ? O2 H2 0.84(3) . ? C8 H8A 1.01(2) . ? C8 H8B 1.02(2) . ? N1 O3 1.218(2) . ? N1 O4 1.220(2) . ? C9 C10 1.325(3) . ? C9 H9 0.90(2) . ? C10 C11 1.473(2) . ? C10 H10 0.92(2) . ? C11 C16 1.392(3) . ? C11 C12 1.405(3) . ? C12 C13 1.396(3) . ? C12 H12 1.00(3) . ? C13 C14 1.379(4) . ? C13 H13A 0.9500 . ? C14 C15 1.382(5) . ? C14 H14 0.97(3) . ? C15 C16 1.397(3) . ? C15 H15 0.89(4) . ? C16 H16 1.01(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 111.82(14) . . ? N1 C1 C7 108.51(13) . . ? C2 C1 C7 106.01(13) . . ? N1 C1 H1 103.0(13) . . ? C2 C1 H1 114.7(13) . . ? C7 C1 H1 112.7(12) . . ? C9 C2 C1 116.37(14) . . ? C9 C2 C3 116.64(14) . . ? C1 C2 C3 104.66(13) . . ? C9 C2 H2A 104.4(12) . . ? C1 C2 H2A 110.5(13) . . ? C3 C2 H2A 103.5(13) . . ? C4 C3 C8 108.64(14) . . ? C4 C3 C2 112.44(13) . . ? C8 C3 C2 101.17(12) . . ? C4 C3 H3 108.7(12) . . ? C8 C3 H3 114.1(13) . . ? C2 C3 H3 111.7(12) . . ? O1 C4 C5 121.81(16) . . ? O1 C4 C3 122.28(15) . . ? C5 C4 C3 115.91(14) . . ? C4 C5 C6 112.96(14) . . ? C4 C5 H5A 108.3(14) . . ? C6 C5 H5A 110.2(14) . . ? C4 C5 H5B 106.4(13) . . ? C6 C5 H5B 110.4(13) . . ? H5A C5 H5B 108.5(19) . . ? C7 C6 C5 112.55(14) . . ? C7 C6 H6A 110.4(13) . . ? C5 C6 H6A 108.2(13) . . ? C7 C6 H6B 107.5(13) . . ? C5 C6 H6B 112.4(12) . . ? H6A C6 H6B 105.6(18) . . ? O2 C7 C8 110.31(13) . . ? O2 C7 C6 111.71(13) . . ? C8 C7 C6 109.34(13) . . ? O2 C7 C1 114.00(13) . . ? C8 C7 C1 102.98(13) . . ? C6 C7 C1 108.10(13) . . ? C7 O2 H2 108.2(18) . . ? C7 C8 C3 101.18(12) . . ? C7 C8 H8A 112.1(12) . . ? C3 C8 H8A 110.5(12) . . ? C7 C8 H8B 111.0(12) . . ? C3 C8 H8B 113.2(13) . . ? H8A C8 H8B 108.7(17) . . ? O3 N1 O4 124.01(19) . . ? O3 N1 C1 116.25(18) . . ? O4 N1 C1 119.64(16) . . ? C10 C9 C2 125.94(17) . . ? C10 C9 H9 118.2(14) . . ? C2 C9 H9 115.6(14) . . ? C9 C10 C11 127.08(18) . . ? C9 C10 H10 119.1(14) . . ? C11 C10 H10 113.8(14) . . ? C16 C11 C12 118.6(2) . . ? C16 C11 C10 118.9(2) . . ? C12 C11 C10 122.47(18) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 121.5(15) . . ? C11 C12 H12 118.4(15) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 119.8(2) . . ? C13 C14 H14 118(2) . . ? C15 C14 H14 122(2) . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15 124(2) . . ? C16 C15 H15 115(2) . . ? C11 C16 C15 120.6(3) . . ? C11 C16 H16 118.7(17) . . ? C15 C16 H16 120.5(17) . . ? 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 N1 C1 C2 C9 102.20(17) . . . . ? C7 C1 C2 C9 -139.73(15) . . . . ? N1 C1 C2 C3 -127.49(14) . . . . ? C7 C1 C2 C3 -9.42(16) . . . . ? C9 C2 C3 C4 50.08(19) . . . . ? C1 C2 C3 C4 -80.07(16) . . . . ? C9 C2 C3 C8 165.80(14) . . . . ? C1 C2 C3 C8 35.64(16) . . . . ? C8 C3 C4 O1 125.41(16) . . . . ? C2 C3 C4 O1 -123.46(17) . . . . ? C8 C3 C4 C5 -55.86(18) . . . . ? C2 C3 C4 C5 55.27(18) . . . . ? O1 C4 C5 C6 -143.33(16) . . . . ? C3 C4 C5 C6 37.9(2) . . . . ? C4 C5 C6 C7 -37.9(2) . . . . ? C5 C6 C7 O2 -179.87(14) . . . . ? C5 C6 C7 C8 57.74(17) . . . . ? C5 C6 C7 C1 -53.67(17) . . . . ? N1 C1 C7 O2 -19.84(19) . . . . ? C2 C1 C7 O2 -140.09(14) . . . . ? N1 C1 C7 C8 99.66(15) . . . . ? C2 C1 C7 C8 -20.59(16) . . . . ? N1 C1 C7 C6 -144.69(14) . . . . ? C2 C1 C7 C6 95.05(15) . . . . ? O2 C7 C8 C3 164.81(14) . . . . ? C6 C7 C8 C3 -71.97(15) . . . . ? C1 C7 C8 C3 42.78(15) . . . . ? C4 C3 C8 C7 69.84(15) . . . . ? C2 C3 C8 C7 -48.67(15) . . . . ? C2 C1 N1 O3 -144.57(18) . . . . ? C7 C1 N1 O3 98.9(2) . . . . ? C2 C1 N1 O4 38.9(2) . . . . ? C7 C1 N1 O4 -77.66(19) . . . . ? C1 C2 C9 C10 -20.1(2) . . . . ? C3 C2 C9 C10 -144.45(18) . . . . ? C2 C9 C10 C11 -174.41(16) . . . . ? C9 C10 C11 C16 -178.31(18) . . . . ? C9 C10 C11 C12 3.1(3) . . . . ? C16 C11 C12 C13 0.0(3) . . . . ? C10 C11 C12 C13 178.52(17) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C12 C11 C16 C15 0.1(3) . . . . ? C10 C11 C16 C15 -178.50(18) . . . . ? C14 C15 C16 C11 0.0(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 O2 H2 O1 0.84(3) 2.01(3) 2.8506(19) 177(2) 1_556 _refine_diff_density_max 0.303 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.043 _shelxl_version_number 2012-6 _iucr_refine_instruction_details ; TITL 3a in P2(1)2(1)2 CELL 0.71073 10.3329 19.6202 7.1804 90.000 90.000 90.000 ZERR 4.00 0.0010 0.0019 0.0007 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, Z SYMM 0.5-X, 0.5+Y, -Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O UNIT 64 68 4 16 TEMP -123 SIZE 0.17 0.21 0.70 ACTA CONF WPDB -1 L.S. 6 BOND $H FMAP 2 PLAN 10 EQIV $1 x, y, z+1 HTAB O2 O1_$1 REM EXTI 0.000000 insig. WGHT 0.067500 FVAR 0.15967 C1 1 0.681013 0.694945 0.396282 11.00000 0.02536 0.02634 = 0.02183 0.00105 0.00135 -0.00251 H1 2 0.590773 0.696605 0.437216 11.00000 -1.20000 C2 1 0.700540 0.669926 0.195659 11.00000 0.02209 0.02533 = 0.02175 -0.00007 0.00319 -0.00150 H2A 2 0.767490 0.637155 0.190508 11.00000 -1.20000 C3 1 0.758662 0.732385 0.090649 11.00000 0.02157 0.03043 = 0.02089 0.00023 0.00368 -0.00220 H3 2 0.804963 0.718838 -0.018114 11.00000 -1.20000 C4 1 0.656530 0.783685 0.035196 11.00000 0.02436 0.02676 = 0.02488 0.00134 -0.00156 -0.00496 O1 4 0.640926 0.801686 -0.126380 11.00000 0.03820 0.03625 = 0.02495 0.00438 -0.00504 -0.00581 C5 1 0.572701 0.810373 0.190883 11.00000 0.02629 0.03328 = 0.02865 0.00186 -0.00186 0.00360 H5A 2 0.534100 0.852339 0.150587 11.00000 -1.20000 H5B 2 0.503291 0.776462 0.209268 11.00000 -1.20000 C6 1 0.648124 0.821479 0.373856 11.00000 0.02846 0.02787 = 0.02465 -0.00243 0.00104 -0.00005 H6A 2 0.689492 0.866994 0.368518 11.00000 -1.20000 H6B 2 0.590932 0.822658 0.483486 11.00000 -1.20000 C7 1 0.749924 0.766094 0.408158 11.00000 0.02358 0.02540 = 0.02123 -0.00027 -0.00079 -0.00352 O2 4 0.817701 0.777047 0.576360 11.00000 0.03118 0.03703 = 0.02430 -0.00257 -0.00606 -0.00369 H2 2 0.763095 0.784410 0.661136 11.00000 -1.50000 C8 1 0.844331 0.764119 0.243740 11.00000 0.02051 0.03153 = 0.02671 0.00186 0.00193 -0.00483 H8A 2 0.922009 0.734016 0.269882 11.00000 -1.20000 H8B 2 0.876357 0.811798 0.211437 11.00000 -1.20000 N1 3 0.742989 0.647761 0.535877 11.00000 0.05874 0.02781 = 0.02556 0.00177 -0.00450 -0.00381 O3 4 0.686180 0.640778 0.683342 11.00000 0.11723 0.05412 = 0.03134 0.01756 0.01848 0.01067 O4 4 0.847485 0.621821 0.500707 11.00000 0.05301 0.04503 = 0.04726 0.00423 -0.01773 0.00861 C9 1 0.586846 0.635409 0.105929 11.00000 0.02686 0.02795 = 0.02405 -0.00305 -0.00051 -0.00338 H9 2 0.592558 0.629481 -0.018403 11.00000 -1.20000 C10 1 0.487195 0.607813 0.194273 11.00000 0.02669 0.02760 = 0.03065 -0.00395 0.00001 -0.00205 H10 2 0.482111 0.611808 0.321455 11.00000 -1.20000 C11 1 0.380099 0.568651 0.111200 11.00000 0.02347 0.02070 = 0.05208 -0.00154 -0.00253 0.00098 C12 1 0.375086 0.552922 -0.079554 11.00000 0.03751 0.02222 = 0.05426 -0.00059 -0.01536 0.00134 H12 2 0.447506 0.568613 -0.160920 11.00000 -1.20000 C13 1 0.272741 0.514283 -0.150138 11.00000 0.05439 0.02565 = 0.07991 -0.00334 -0.03798 0.00020 AFIX 43 H13A 2 0.269749 0.503927 -0.279309 11.00000 -1.20000 AFIX 0 C14 1 0.175978 0.491013 -0.034177 11.00000 0.03450 0.02880 = 0.12316 -0.00297 -0.03171 -0.00264 H14 2 0.105836 0.464720 -0.089217 11.00000 -1.20000 C15 1 0.179812 0.506312 0.153561 11.00000 0.02470 0.03164 = 0.12305 0.00345 0.00200 -0.00244 H15 2 0.119689 0.493456 0.235687 11.00000 -1.20000 C16 1 0.281442 0.544974 0.226363 11.00000 0.02634 0.03015 = 0.07786 -0.00143 0.00838 0.00051 H16 2 0.280822 0.559497 0.361306 11.00000 -1.20000 HKLF 4 REM am2 in P2(1)2(1)2 REM R1 = 0.0412 for 3804 Fo > 4sig(Fo) and 0.0500 for all 4410 data REM 238 parameters refined using 0 restraints END WGHT 0.0676 0.0000 REM Highest difference peak 0.303, deepest hole -0.147, 1-sigma level 0.043 Q1 1 0.7974 0.7668 0.3294 11.00000 0.05 0.30 Q2 1 0.7201 0.7307 0.4133 11.00000 0.05 0.30 Q3 1 0.7048 0.6834 0.2996 11.00000 0.05 0.30 Q4 1 0.7155 0.6711 0.4493 11.00000 0.05 0.27 Q5 1 0.8020 0.7475 0.1457 11.00000 0.05 0.26 Q6 1 0.7213 0.7013 0.1403 11.00000 0.05 0.24 Q7 1 0.3067 0.5477 -0.1076 11.00000 0.05 0.23 Q8 1 0.6999 0.7899 0.3716 11.00000 0.05 0.23 Q9 1 0.6419 0.6175 0.6310 11.00000 0.05 0.23 Q10 1 0.6366 0.7759 -0.0628 11.00000 0.05 0.22 ;