# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_11c _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 N2 O3' _chemical_formula_sum 'C13 H16 N2 O3' _chemical_formula_weight 248.28 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 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 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+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9698(12) _cell_length_b 9.5108(16) _cell_length_c 19.233(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1274.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3130 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 23.33 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_F_000 528 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 1.700 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.070 _exptl_absorpt_coefficient_mu 0.093 _shelx_estimated_absorpt_T_min 0.858 _shelx_estimated_absorpt_T_max 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'SADABS v2012/1, Sheldrick, G.M., (2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11350 _diffrn_reflns_av_unetI/netI 0.0283 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.118 _diffrn_reflns_theta_max 26.417 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 2618 _reflns_number_gt 2390 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.710 _reflns_Friedel_fraction_max 0.999 _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-2013 (Sheldrick, 2013)' _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^)+(0.0451P)^2^+0.0725P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.0(6) _chemical_absolute_configuration syn _refine_ls_number_reflns 2618 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N1 N 0.6760(3) 0.47667(18) 0.17030(8) 0.0289(4) Uani 1 1 d . . . . . O1 O 0.6596(2) 0.34386(15) 0.20662(7) 0.0294(4) Uani 1 1 d . . . . . C1 C 0.5953(3) 0.2431(2) 0.16305(10) 0.0251(4) Uani 1 1 d . . . . . C2 C 0.5658(3) 0.3043(2) 0.09976(10) 0.0227(4) Uani 1 1 d . . . . . C3 C 0.6192(3) 0.4450(2) 0.10789(10) 0.0231(4) Uani 1 1 d . . . . . C4 C 0.5887(3) 0.5260(2) 0.04159(9) 0.0225(4) Uani 1 1 d . . . . . H4 H 0.704(3) 0.563(2) 0.0234(11) 0.020(5) Uiso 1 1 d . . . . . N2 N 0.5322(2) 0.40813(16) -0.00600(8) 0.0219(4) Uani 1 1 d . . . . . C5 C 0.5092(3) 0.2767(2) 0.02828(9) 0.0215(4) Uani 1 1 d . . . . . O2 O 0.4512(2) 0.16826(13) 0.00244(7) 0.0276(3) Uani 1 1 d . . . . . C6 C 0.5773(4) 0.0993(2) 0.19076(12) 0.0341(5) Uani 1 1 d . . . . . H6A H 0.491(5) 0.044(3) 0.1630(16) 0.068(9) Uiso 1 1 d . . . . . H6B H 0.690(7) 0.052(4) 0.191(2) 0.100(13) Uiso 1 1 d . . . . . H6C H 0.506(4) 0.092(3) 0.2330(14) 0.055(8) Uiso 1 1 d . . . . . C7 C 0.4362(3) 0.6423(2) 0.04790(11) 0.0273(5) Uani 1 1 d . . . . . H7 H 0.416(3) 0.679(2) 0.0018(11) 0.025(5) Uiso 1 1 d . . . . . C8 C 0.5136(4) 0.7610(2) 0.09322(13) 0.0359(5) Uani 1 1 d . . . . . H8A H 0.644(4) 0.802(2) 0.0798(14) 0.039(7) Uiso 1 1 d . . . . . H8B H 0.419(4) 0.842(3) 0.0956(14) 0.058(8) Uiso 1 1 d . . . . . H8C H 0.536(4) 0.731(2) 0.1422(14) 0.041(7) Uiso 1 1 d . . . . . C9 C 0.2457(3) 0.5881(3) 0.07569(14) 0.0353(5) Uani 1 1 d . . . . . H9A H 0.196(4) 0.512(3) 0.0474(13) 0.037(6) Uiso 1 1 d . . . . . H9B H 0.257(4) 0.549(3) 0.1259(14) 0.046(7) Uiso 1 1 d . . . . . H9C H 0.147(4) 0.667(3) 0.0803(15) 0.052(8) Uiso 1 1 d . . . . . C10 C 0.5543(3) 0.4308(2) -0.07795(10) 0.0245(4) Uani 1 1 d . . . . . O3 O 0.5795(3) 0.55123(15) -0.09796(7) 0.0363(4) Uani 1 1 d . . . . . C11 C 0.5554(3) 0.3089(2) -0.12532(10) 0.0253(4) Uani 1 1 d . . . . . H11 H 0.532(3) 0.216(2) -0.1071(11) 0.029(6) Uiso 1 1 d . . . . . C12 C 0.5902(3) 0.3271(2) -0.19257(10) 0.0284(5) Uani 1 1 d . . . . . H12 H 0.610(4) 0.422(3) -0.2100(12) 0.036(6) Uiso 1 1 d . . . . . C13 C 0.6051(4) 0.2113(3) -0.24419(13) 0.0388(6) Uani 1 1 d . . . . . H13A H 0.517(4) 0.226(3) -0.2797(14) 0.047(8) Uiso 1 1 d . . . . . H13B H 0.736(5) 0.208(3) -0.2643(14) 0.054(8) Uiso 1 1 d . . . . . H13C H 0.582(4) 0.116(3) -0.2224(14) 0.056(8) 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 N1 0.0356(10) 0.0286(9) 0.0227(8) -0.0009(7) -0.0024(8) 0.0023(8) O1 0.0361(8) 0.0328(8) 0.0194(6) 0.0008(6) -0.0010(6) 0.0030(7) C1 0.0234(11) 0.0313(11) 0.0207(10) -0.0008(8) 0.0038(8) 0.0054(9) C2 0.0217(10) 0.0246(10) 0.0218(9) -0.0008(8) 0.0022(8) 0.0015(8) C3 0.0207(10) 0.0271(10) 0.0214(9) -0.0017(8) 0.0005(7) 0.0026(8) C4 0.0249(11) 0.0228(10) 0.0197(9) -0.0004(8) -0.0018(8) -0.0020(8) N2 0.0254(9) 0.0211(8) 0.0193(7) -0.0015(6) -0.0012(7) 0.0005(7) C5 0.0185(10) 0.0238(10) 0.0223(9) -0.0002(8) 0.0020(8) 0.0014(8) O2 0.0323(8) 0.0237(7) 0.0267(7) -0.0019(6) 0.0014(6) -0.0048(6) C6 0.0378(14) 0.0342(12) 0.0305(12) 0.0091(10) 0.0035(11) 0.0001(11) C7 0.0321(12) 0.0221(10) 0.0276(10) 0.0009(8) -0.0043(9) 0.0038(9) C8 0.0423(15) 0.0260(11) 0.0395(13) -0.0072(10) -0.0016(11) 0.0006(11) C9 0.0292(12) 0.0310(13) 0.0456(14) -0.0043(11) 0.0009(11) 0.0040(10) C10 0.0255(11) 0.0271(10) 0.0210(9) 0.0013(8) -0.0021(8) 0.0007(9) O3 0.0571(11) 0.0265(8) 0.0252(7) 0.0026(6) -0.0015(7) -0.0045(7) C11 0.0249(11) 0.0278(10) 0.0231(9) -0.0002(8) -0.0009(9) -0.0013(9) C12 0.0273(11) 0.0331(11) 0.0246(10) -0.0018(9) 0.0001(8) -0.0020(10) C13 0.0413(15) 0.0479(16) 0.0272(12) -0.0093(11) 0.0070(11) -0.0074(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.299(3) . ? N1 O1 1.448(2) . ? O1 C1 1.350(2) . ? C1 C2 1.365(3) . ? C1 C6 1.473(3) . ? C2 C3 1.397(3) . ? C2 C5 1.454(3) . ? C3 C4 1.505(3) . ? C4 N2 1.500(2) . ? C4 C7 1.539(3) . ? C4 H4 0.95(2) . ? N2 C10 1.409(2) . ? N2 C5 1.422(2) . ? C5 O2 1.214(2) . ? C6 H6A 0.96(3) . ? C6 H6B 0.91(4) . ? C6 H6C 0.95(3) . ? C7 C9 1.521(3) . ? C7 C8 1.525(3) . ? C7 H7 0.96(2) . ? C8 H8A 1.02(3) . ? C8 H8B 1.02(3) . ? C8 H8C 1.00(3) . ? C9 H9A 0.97(3) . ? C9 H9B 1.04(3) . ? C9 H9C 1.02(3) . ? C10 O3 1.221(2) . ? C10 C11 1.475(3) . ? C11 C12 1.327(3) . ? C11 H11 0.97(2) . ? C12 C13 1.486(3) . ? C12 H12 0.97(2) . ? C13 H13A 0.93(3) . ? C13 H13B 0.99(3) . ? C13 H13C 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 C3 N1 O1 102.66(15) . . ? C1 O1 N1 110.25(14) . . ? O1 C1 C2 107.52(17) . . ? O1 C1 C6 117.57(17) . . ? C2 C1 C6 134.88(19) . . ? C1 C2 C3 105.56(17) . . ? C1 C2 C5 143.81(19) . . ? C3 C2 C5 110.54(16) . . ? N1 C3 C2 114.00(18) . . ? N1 C3 C4 134.98(18) . . ? C2 C3 C4 110.96(16) . . ? N2 C4 C3 99.88(14) . . ? N2 C4 C7 113.83(16) . . ? C3 C4 C7 113.49(16) . . ? N2 C4 H4 106.1(13) . . ? C3 C4 H4 112.7(13) . . ? C7 C4 H4 110.3(13) . . ? C10 N2 C5 127.03(15) . . ? C10 N2 C4 117.15(15) . . ? C5 N2 C4 113.81(14) . . ? O2 C5 N2 126.48(17) . . ? O2 C5 C2 129.10(18) . . ? N2 C5 C2 104.41(15) . . ? C1 C6 H6A 111.2(17) . . ? C1 C6 H6B 113(3) . . ? H6A C6 H6B 106(3) . . ? C1 C6 H6C 115.0(17) . . ? H6A C6 H6C 96(2) . . ? H6B C6 H6C 114(3) . . ? C9 C7 C8 111.03(19) . . ? C9 C7 C4 112.79(17) . . ? C8 C7 C4 109.44(19) . . ? C9 C7 H7 108.7(13) . . ? C8 C7 H7 108.1(12) . . ? C4 C7 H7 106.6(12) . . ? C7 C8 H8A 117.0(14) . . ? C7 C8 H8B 110.9(16) . . ? H8A C8 H8B 107(2) . . ? C7 C8 H8C 112.3(14) . . ? H8A C8 H8C 102(2) . . ? H8B C8 H8C 106(2) . . ? C7 C9 H9A 111.5(15) . . ? C7 C9 H9B 112.6(15) . . ? H9A C9 H9B 106.4(19) . . ? C7 C9 H9C 111.5(15) . . ? H9A C9 H9C 111(2) . . ? H9B C9 H9C 103(2) . . ? O3 C10 N2 117.98(17) . . ? O3 C10 C11 122.82(17) . . ? N2 C10 C11 119.13(16) . . ? C12 C11 C10 120.02(19) . . ? C12 C11 H11 120.3(12) . . ? C10 C11 H11 119.7(13) . . ? C11 C12 C13 124.5(2) . . ? C11 C12 H12 118.9(14) . . ? C13 C12 H12 116.6(14) . . ? C12 C13 H13A 109.7(16) . . ? C12 C13 H13B 110.3(16) . . ? H13A C13 H13B 109(2) . . ? C12 C13 H13C 112.1(15) . . ? H13A C13 H13C 109(2) . . ? H13B C13 H13C 106(2) . . ? 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 C3 N1 O1 C1 0.3(2) . . . . ? N1 O1 C1 C2 -0.9(2) . . . . ? N1 O1 C1 C6 177.61(19) . . . . ? O1 C1 C2 C3 1.1(2) . . . . ? C6 C1 C2 C3 -177.0(2) . . . . ? O1 C1 C2 C5 177.2(3) . . . . ? C6 C1 C2 C5 -1.0(5) . . . . ? O1 N1 C3 C2 0.4(2) . . . . ? O1 N1 C3 C4 177.3(2) . . . . ? C1 C2 C3 N1 -0.9(2) . . . . ? C5 C2 C3 N1 -178.48(18) . . . . ? C1 C2 C3 C4 -178.61(17) . . . . ? C5 C2 C3 C4 3.9(2) . . . . ? N1 C3 C4 N2 177.1(2) . . . . ? C2 C3 C4 N2 -5.9(2) . . . . ? N1 C3 C4 C7 -61.4(3) . . . . ? C2 C3 C4 C7 115.6(2) . . . . ? C3 C4 N2 C10 -158.75(16) . . . . ? C7 C4 N2 C10 80.0(2) . . . . ? C3 C4 N2 C5 6.3(2) . . . . ? C7 C4 N2 C5 -115.02(18) . . . . ? C10 N2 C5 O2 -22.4(3) . . . . ? C4 N2 C5 O2 174.39(19) . . . . ? C10 N2 C5 C2 158.92(19) . . . . ? C4 N2 C5 C2 -4.3(2) . . . . ? C1 C2 C5 O2 5.6(5) . . . . ? C3 C2 C5 O2 -178.4(2) . . . . ? C1 C2 C5 N2 -175.7(3) . . . . ? C3 C2 C5 N2 0.2(2) . . . . ? N2 C4 C7 C9 59.8(2) . . . . ? C3 C4 C7 C9 -53.6(2) . . . . ? N2 C4 C7 C8 -176.08(16) . . . . ? C3 C4 C7 C8 70.6(2) . . . . ? C5 N2 C10 O3 -177.35(19) . . . . ? C4 N2 C10 O3 -14.6(3) . . . . ? C5 N2 C10 C11 -0.3(3) . . . . ? C4 N2 C10 C11 162.47(17) . . . . ? O3 C10 C11 C12 1.9(3) . . . . ? N2 C10 C11 C12 -175.02(19) . . . . ? C10 C11 C12 C13 176.6(2) . . . . ? _refine_diff_density_max 0.161 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.031 _shelxl_version_number 2013-3 _iucr_refine_instruction_details ; TITL 11c in P2(1)2(1)2(1) CELL 0.71073 6.9698 9.5108 19.2327 90.000 90.000 90.000 ZERR 4.00 0.0012 0.0016 0.0033 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O UNIT 52 64 8 12 TEMP -123 SIZE 0.07 0.28 1.70 BOND $H ACTA CONF WPDB -1 L.S. 4 BOND FMAP 2 PLAN 10 REM EXTI 0.000204 insig. WGHT 0.045100 0.072500 FVAR 0.23702 N1 3 0.675989 0.476671 0.170301 11.00000 0.03555 0.02855 = 0.02268 -0.00095 -0.00242 0.00227 O1 4 0.659602 0.343864 0.206620 11.00000 0.03607 0.03276 = 0.01942 0.00077 -0.00101 0.00301 C1 1 0.595265 0.243101 0.163053 11.00000 0.02341 0.03131 = 0.02066 -0.00083 0.00382 0.00536 C2 1 0.565783 0.304290 0.099755 11.00000 0.02171 0.02464 = 0.02182 -0.00082 0.00222 0.00147 C3 1 0.619175 0.444964 0.107890 11.00000 0.02071 0.02711 = 0.02136 -0.00169 0.00050 0.00261 C4 1 0.588727 0.525962 0.041590 11.00000 0.02489 0.02283 = 0.01970 -0.00037 -0.00183 -0.00198 H4 2 0.703980 0.563263 0.023370 11.00000 0.02035 N2 3 0.532248 0.408127 -0.005996 11.00000 0.02537 0.02106 = 0.01925 -0.00150 -0.00118 0.00054 C5 1 0.509179 0.276689 0.028280 11.00000 0.01852 0.02382 = 0.02225 -0.00015 0.00199 0.00142 O2 4 0.451215 0.168258 0.002445 11.00000 0.03228 0.02366 = 0.02672 -0.00194 0.00144 -0.00476 C6 1 0.577333 0.099274 0.190759 11.00000 0.03779 0.03418 = 0.03047 0.00910 0.00350 0.00006 H6A 2 0.490633 0.043819 0.162985 11.00000 0.06799 H6B 2 0.690065 0.051873 0.190858 11.00000 0.09976 H6C 2 0.506450 0.091589 0.233043 11.00000 0.05487 C7 1 0.436216 0.642267 0.047902 11.00000 0.03210 0.02210 = 0.02760 0.00090 -0.00425 0.00377 H7 2 0.416463 0.678732 0.001820 11.00000 0.02456 C8 1 0.513649 0.760984 0.093220 11.00000 0.04226 0.02595 = 0.03948 -0.00719 -0.00161 0.00055 H8A 2 0.643928 0.802215 0.079825 11.00000 0.03913 H8B 2 0.418605 0.842277 0.095615 11.00000 0.05786 H8C 2 0.535810 0.730608 0.142222 11.00000 0.04060 C9 1 0.245670 0.588109 0.075691 11.00000 0.02920 0.03104 = 0.04559 -0.00435 0.00086 0.00402 H9A 2 0.196336 0.511947 0.047411 11.00000 0.03651 H9B 2 0.256572 0.549295 0.125944 11.00000 0.04594 H9C 2 0.147180 0.667375 0.080309 11.00000 0.05236 C10 1 0.554275 0.430833 -0.077947 11.00000 0.02551 0.02707 = 0.02099 0.00127 -0.00209 0.00066 O3 4 0.579505 0.551230 -0.097962 11.00000 0.05714 0.02654 = 0.02518 0.00260 -0.00148 -0.00452 C11 1 0.555448 0.308891 -0.125317 11.00000 0.02489 0.02778 = 0.02310 -0.00023 -0.00092 -0.00134 H11 2 0.531778 0.215855 -0.107105 11.00000 0.02902 C12 1 0.590164 0.327109 -0.192574 11.00000 0.02734 0.03314 = 0.02460 -0.00182 0.00008 -0.00200 H12 2 0.609901 0.421898 -0.209986 11.00000 0.03629 C13 1 0.605079 0.211325 -0.244194 11.00000 0.04131 0.04791 = 0.02721 -0.00926 0.00695 -0.00738 H13A 2 0.516576 0.225555 -0.279727 11.00000 0.04720 H13B 2 0.736285 0.207977 -0.264261 11.00000 0.05415 H13C 2 0.581988 0.116318 -0.222448 11.00000 0.05635 HKLF 4 REM 11c in P2(1)2(1)2(1) REM R1 = 0.0318 for 2390 Fo > 4sig(Fo) and 0.0364 for all 2618 data REM 227 parameters refined using 0 restraints END WGHT 0.0451 0.0725 REM Highest difference peak 0.161, deepest hole -0.150, 1-sigma level 0.031 Q1 1 0.5023 0.3192 -0.1618 11.00000 0.05 0.16 Q2 1 0.6063 0.4920 0.0797 11.00000 0.05 0.15 Q3 1 0.5640 0.2585 0.1256 11.00000 0.05 0.15 Q4 1 0.6980 0.0985 0.2279 11.00000 0.05 0.14 Q5 1 0.4929 0.2883 0.0735 11.00000 0.05 0.13 Q6 1 0.5559 0.4061 -0.0345 11.00000 0.05 0.13 Q7 1 0.5514 0.2829 0.0734 11.00000 0.05 0.12 Q8 1 0.5803 0.3749 0.1041 11.00000 0.05 0.12 Q9 1 0.4996 0.5764 0.0520 11.00000 0.05 0.12 Q10 1 0.6159 0.1338 0.2481 11.00000 0.05 0.12 ; _database_code_depnum_ccdc_archive 'CCDC 959645'