# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2019 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_cu_llg14_0m _database_code_depnum_ccdc_archive 'CCDC 1561836' _audit_update_record ; 2017-07-12 deposited with the CCDC. 2019-11-04 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 O2' _chemical_formula_sum 'C15 H22 O2' _chemical_formula_weight 234.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.70800(10) _cell_length_b 12.5490(2) _cell_length_c 13.1278(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1269.82(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7699 _cell_measurement_theta_min 4.88 _cell_measurement_theta_max 70.19 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_F_000 512 _exptl_transmission_factor_min 0.2612 _exptl_transmission_factor_max 0.5857 _exptl_crystal_size_max 0.850 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.190 _exptl_absorpt_coefficient_mu 0.621 _shelx_estimated_absorpt_T_min 0.620 _shelx_estimated_absorpt_T_max 0.891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details sadabs _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8045 _diffrn_reflns_av_unetI/netI 0.0338 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.875 _diffrn_reflns_theta_max 70.187 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.952 _diffrn_reflns_point_group_measured_fraction_full 0.978 _reflns_number_total 2306 _reflns_number_gt 2295 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.677 _reflns_Friedel_fraction_max 0.922 _reflns_Friedel_fraction_full 0.957 _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 APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _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^)+(0.1009P)^2^+0.1800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.0064(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.09(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 2306 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1314 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 O1 O 0.0684(2) 0.24653(15) 0.51563(13) 0.0365(5) Uani 1 1 d . . . . . O2 O 0.5254(2) 0.40443(14) 0.32442(14) 0.0337(5) Uani 1 1 d . . . . . H7 H 0.558(5) 0.341(3) 0.372(3) 0.051 Uiso 1 1 d . U . . . C1 C 0.2895(3) 0.52193(16) 0.29879(18) 0.0270(5) Uani 1 1 d . . . . . H6 H 0.3814 0.5735 0.3172 0.032 Uiso 1 1 calc R U . . . H1 H 0.1796 0.5438 0.3318 0.032 Uiso 1 1 calc R U . . . C2 C 0.3402(3) 0.40927(17) 0.33049(18) 0.0250(5) Uani 1 1 d . . . . . H8 H 0.3006 0.3944 0.4016 0.030 Uiso 1 1 calc R U . . . C3 C 0.2497(3) 0.33199(16) 0.25387(15) 0.0220(5) Uani 1 1 d . . . . . C4 C 0.0758(3) 0.28389(14) 0.29473(17) 0.0235(5) Uani 1 1 d . . . . . H22 H 0.0940 0.2098 0.3207 0.028 Uiso 1 1 calc R U . . . C5 C -0.0134(3) 0.35194(17) 0.37373(18) 0.0238(5) Uani 1 1 d . . . . . C6 C -0.0121(3) 0.32177(19) 0.48110(18) 0.0292(5) Uani 1 1 d . . . . . H2 H -0.0785 0.3636 0.5271 0.035 Uiso 1 1 calc R U . . . C7 C 0.1925(3) 0.40399(16) 0.15990(17) 0.0240(5) Uani 1 1 d . . . . . C8 C 0.2670(4) 0.3666(2) 0.05758(19) 0.0352(6) Uani 1 1 d . . . . . H4 H 0.2360 0.4179 0.0043 0.053 Uiso 1 1 calc R U . . . H3 H 0.2189 0.2966 0.0405 0.053 Uiso 1 1 calc R U . . . H5 H 0.3936 0.3615 0.0626 0.053 Uiso 1 1 calc R U . . . C9 C 0.2677(3) 0.51537(17) 0.18308(17) 0.0264(5) Uani 1 1 d . . . . . H9 H 0.3811 0.5247 0.1488 0.032 Uiso 1 1 calc R U . . . H10 H 0.1877 0.5716 0.1588 0.032 Uiso 1 1 calc R U . . . C10 C -0.0132(3) 0.39770(17) 0.15983(18) 0.0265(5) Uani 1 1 d . . . . . C11 C -0.1046(3) 0.47345(17) 0.23524(19) 0.0290(5) Uani 1 1 d . . . . . H12 H -0.0517 0.5450 0.2289 0.035 Uiso 1 1 calc R U . . . H11 H -0.2279 0.4798 0.2151 0.035 Uiso 1 1 calc R U . . . C12 C -0.0971(3) 0.44042(17) 0.34471(19) 0.0282(5) Uani 1 1 d . . . . . H13 H -0.1528 0.4831 0.3947 0.034 Uiso 1 1 calc R U . . . C13 C -0.0399(3) 0.28327(16) 0.19956(18) 0.0293(5) Uani 1 1 d . . . . . H15 H -0.1628 0.2697 0.2171 0.035 Uiso 1 1 calc R U . . . H14 H -0.0004 0.2296 0.1493 0.035 Uiso 1 1 calc R U . . . C14 C -0.0937(4) 0.4166(2) 0.0548(2) 0.0377(6) Uani 1 1 d . . . . . H17 H -0.0487 0.3638 0.0065 0.057 Uiso 1 1 calc R U . . . H16 H -0.0639 0.4884 0.0311 0.057 Uiso 1 1 calc R U . . . H18 H -0.2201 0.4098 0.0594 0.057 Uiso 1 1 calc R U . . . C15 C 0.3689(3) 0.23847(18) 0.22755(19) 0.0312(5) Uani 1 1 d . . . . . H20 H 0.4739 0.2653 0.1942 0.047 Uiso 1 1 calc R U . . . H19 H 0.3083 0.1895 0.1815 0.047 Uiso 1 1 calc R U . . . H21 H 0.4009 0.2006 0.2901 0.047 Uiso 1 1 calc R 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 O1 0.0328(9) 0.0398(9) 0.0370(9) 0.0109(8) 0.0018(7) 0.0003(8) O2 0.0211(8) 0.0398(10) 0.0402(9) 0.0087(8) -0.0012(7) -0.0038(7) C1 0.0280(11) 0.0191(9) 0.0338(12) 0.0004(8) 0.0009(9) -0.0062(9) C2 0.0219(10) 0.0239(10) 0.0293(11) 0.0014(9) 0.0016(8) -0.0023(8) C3 0.0226(10) 0.0174(9) 0.0261(10) 0.0024(7) 0.0022(8) 0.0024(7) C4 0.0265(10) 0.0122(9) 0.0319(11) 0.0018(8) -0.0006(9) -0.0012(8) C5 0.0175(9) 0.0202(10) 0.0335(11) 0.0006(8) 0.0027(8) -0.0051(8) C6 0.0234(10) 0.0303(11) 0.0339(12) 0.0016(10) 0.0047(9) -0.0049(9) C7 0.0258(11) 0.0181(9) 0.0280(11) 0.0020(9) 0.0022(8) 0.0013(8) C8 0.0407(13) 0.0346(12) 0.0302(12) 0.0020(10) 0.0054(10) 0.0074(11) C9 0.0240(10) 0.0212(10) 0.0341(12) 0.0078(9) 0.0029(8) -0.0027(8) C10 0.0282(11) 0.0197(10) 0.0317(10) 0.0051(9) -0.0068(9) -0.0020(8) C11 0.0225(10) 0.0201(9) 0.0444(13) 0.0054(9) -0.0009(9) 0.0003(9) C12 0.0233(10) 0.0224(10) 0.0389(12) -0.0011(9) 0.0072(10) -0.0010(8) C13 0.0337(12) 0.0185(10) 0.0357(12) 0.0007(9) -0.0061(10) -0.0051(8) C14 0.0383(13) 0.0372(12) 0.0376(13) 0.0070(10) -0.0117(11) -0.0057(11) C15 0.0336(12) 0.0248(10) 0.0353(12) 0.0019(9) 0.0045(10) 0.0110(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.217(3) . ? O2 C2 1.431(3) . ? O2 H7 1.04(4) . ? C1 C2 1.525(3) . ? C1 C9 1.530(3) . ? C1 H6 0.9900 . ? C1 H1 0.9900 . ? C2 C3 1.562(3) . ? C2 H8 1.0000 . ? C3 C15 1.530(3) . ? C3 C4 1.565(3) . ? C3 C7 1.591(3) . ? C4 C5 1.509(3) . ? C4 C13 1.535(3) . ? C4 H22 1.0000 . ? C5 C12 1.339(3) . ? C5 C6 1.460(3) . ? C6 H2 0.9500 . ? C7 C8 1.534(3) . ? C7 C9 1.544(3) . ? C7 C10 1.587(3) . ? C8 H4 0.9800 . ? C8 H3 0.9800 . ? C8 H5 0.9800 . ? C9 H9 0.9900 . ? C9 H10 0.9900 . ? C10 C14 1.531(3) . ? C10 C13 1.541(3) . ? C10 C11 1.543(3) . ? C11 C12 1.497(3) . ? C11 H12 0.9900 . ? C11 H11 0.9900 . ? C12 H13 0.9500 . ? C13 H15 0.9900 . ? C13 H14 0.9900 . ? C14 H17 0.9800 . ? C14 H16 0.9800 . ? C14 H18 0.9800 . ? C15 H20 0.9800 . ? C15 H19 0.9800 . ? C15 H21 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 C2 O2 H7 104(2) . . ? C2 C1 C9 104.42(18) . . ? C2 C1 H6 110.9 . . ? C9 C1 H6 110.9 . . ? C2 C1 H1 110.9 . . ? C9 C1 H1 110.9 . . ? H6 C1 H1 108.9 . . ? O2 C2 C1 106.26(18) . . ? O2 C2 C3 112.55(18) . . ? C1 C2 C3 106.58(18) . . ? O2 C2 H8 110.4 . . ? C1 C2 H8 110.4 . . ? C3 C2 H8 110.4 . . ? C15 C3 C2 110.68(18) . . ? C15 C3 C4 107.23(17) . . ? C2 C3 C4 113.67(17) . . ? C15 C3 C7 115.26(17) . . ? C2 C3 C7 105.69(17) . . ? C4 C3 C7 104.33(15) . . ? C5 C4 C13 107.32(18) . . ? C5 C4 C3 114.06(16) . . ? C13 C4 C3 102.73(17) . . ? C5 C4 H22 110.8 . . ? C13 C4 H22 110.8 . . ? C3 C4 H22 110.8 . . ? C12 C5 C6 119.6(2) . . ? C12 C5 C4 119.5(2) . . ? C6 C5 C4 120.91(19) . . ? O1 C6 C5 124.4(2) . . ? O1 C6 H2 117.8 . . ? C5 C6 H2 117.8 . . ? C8 C7 C9 107.99(18) . . ? C8 C7 C10 111.0(2) . . ? C9 C7 C10 114.86(18) . . ? C8 C7 C3 113.67(17) . . ? C9 C7 C3 104.91(17) . . ? C10 C7 C3 104.40(16) . . ? C7 C8 H4 109.5 . . ? C7 C8 H3 109.5 . . ? H4 C8 H3 109.5 . . ? C7 C8 H5 109.5 . . ? H4 C8 H5 109.5 . . ? H3 C8 H5 109.5 . . ? C1 C9 C7 106.59(17) . . ? C1 C9 H9 110.4 . . ? C7 C9 H9 110.4 . . ? C1 C9 H10 110.4 . . ? C7 C9 H10 110.4 . . ? H9 C9 H10 108.6 . . ? C14 C10 C13 113.29(19) . . ? C14 C10 C11 107.3(2) . . ? C13 C10 C11 107.22(19) . . ? C14 C10 C7 113.4(2) . . ? C13 C10 C7 100.33(18) . . ? C11 C10 C7 115.17(19) . . ? C12 C11 C10 115.32(18) . . ? C12 C11 H12 108.4 . . ? C10 C11 H12 108.4 . . ? C12 C11 H11 108.4 . . ? C10 C11 H11 108.4 . . ? H12 C11 H11 107.5 . . ? C5 C12 C11 121.4(2) . . ? C5 C12 H13 119.3 . . ? C11 C12 H13 119.3 . . ? C4 C13 C10 101.14(17) . . ? C4 C13 H15 111.5 . . ? C10 C13 H15 111.5 . . ? C4 C13 H14 111.5 . . ? C10 C13 H14 111.5 . . ? H15 C13 H14 109.4 . . ? C10 C14 H17 109.5 . . ? C10 C14 H16 109.5 . . ? H17 C14 H16 109.5 . . ? C10 C14 H18 109.5 . . ? H17 C14 H18 109.5 . . ? H16 C14 H18 109.5 . . ? C3 C15 H20 109.5 . . ? C3 C15 H19 109.5 . . ? H20 C15 H19 109.5 . . ? C3 C15 H21 109.5 . . ? H20 C15 H21 109.5 . . ? H19 C15 H21 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 C9 C1 C2 O2 88.9(2) . . . . ? C9 C1 C2 C3 -31.4(2) . . . . ? O2 C2 C3 C15 25.5(2) . . . . ? C1 C2 C3 C15 141.61(19) . . . . ? O2 C2 C3 C4 146.24(18) . . . . ? C1 C2 C3 C4 -97.7(2) . . . . ? O2 C2 C3 C7 -99.9(2) . . . . ? C1 C2 C3 C7 16.2(2) . . . . ? C15 C3 C4 C5 148.30(19) . . . . ? C2 C3 C4 C5 25.6(3) . . . . ? C7 C3 C4 C5 -89.0(2) . . . . ? C15 C3 C4 C13 -95.91(18) . . . . ? C2 C3 C4 C13 141.43(17) . . . . ? C7 C3 C4 C13 26.8(2) . . . . ? C13 C4 C5 C12 -38.1(3) . . . . ? C3 C4 C5 C12 75.0(3) . . . . ? C13 C4 C5 C6 140.95(19) . . . . ? C3 C4 C5 C6 -106.0(2) . . . . ? C12 C5 C6 O1 -175.5(2) . . . . ? C4 C5 C6 O1 5.4(3) . . . . ? C15 C3 C7 C8 0.3(3) . . . . ? C2 C3 C7 C8 122.8(2) . . . . ? C4 C3 C7 C8 -117.0(2) . . . . ? C15 C3 C7 C9 -117.5(2) . . . . ? C2 C3 C7 C9 5.1(2) . . . . ? C4 C3 C7 C9 125.21(17) . . . . ? C15 C3 C7 C10 121.3(2) . . . . ? C2 C3 C7 C10 -116.10(18) . . . . ? C4 C3 C7 C10 4.0(2) . . . . ? C2 C1 C9 C7 35.0(2) . . . . ? C8 C7 C9 C1 -146.06(19) . . . . ? C10 C7 C9 C1 89.5(2) . . . . ? C3 C7 C9 C1 -24.5(2) . . . . ? C8 C7 C10 C14 -31.3(3) . . . . ? C9 C7 C10 C14 91.5(2) . . . . ? C3 C7 C10 C14 -154.17(18) . . . . ? C8 C7 C10 C13 89.8(2) . . . . ? C9 C7 C10 C13 -147.34(18) . . . . ? C3 C7 C10 C13 -33.0(2) . . . . ? C8 C7 C10 C11 -155.47(19) . . . . ? C9 C7 C10 C11 -32.6(3) . . . . ? C3 C7 C10 C11 81.7(2) . . . . ? C14 C10 C11 C12 157.36(19) . . . . ? C13 C10 C11 C12 35.4(3) . . . . ? C7 C10 C11 C12 -75.3(2) . . . . ? C6 C5 C12 C11 -178.90(19) . . . . ? C4 C5 C12 C11 0.2(3) . . . . ? C10 C11 C12 C5 1.1(3) . . . . ? C5 C4 C13 C10 71.9(2) . . . . ? C3 C4 C13 C10 -48.7(2) . . . . ? C14 C10 C13 C4 171.6(2) . . . . ? C11 C10 C13 C4 -70.2(2) . . . . ? C7 C10 C13 C4 50.4(2) . . . . ? 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 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556 _refine_diff_density_max 0.292 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.060 _shelx_res_file ; cu_llg14_0m.res created by SHELXL-2014/7 TITL cu_llg14_0m in P2(1)2(1)2(1) CELL 1.54178 7.7080 12.5490 13.1278 90.000 90.000 90.000 ZERR 4.00 0.0001 0.0002 0.0002 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H O UNIT 60 88 8 L.S. 10 ACTA BOND $H FMAP 2 PLAN -4 HTAB O2 O1_$1 HTAB O2 O1_$1 HTAB O2 O1_$1 SIZE 0.190 0.220 0.850 HTAB CONF EQIV $1 x+1/2, -y+1/2, -z+1 HTAB O2 O1_$1 HTAB O2 O1_$1 HTAB O2 O1_$1 HTAB O2 O1_$1 TEMP -173.000 WGHT 0.100900 0.180000 EXTI 0.006419 FVAR 0.28406 O1 3 0.068402 0.246535 0.515635 11.00000 0.03283 0.03980 = 0.03698 0.01093 0.00181 0.00027 O2 3 0.525440 0.404431 0.324417 11.00000 0.02112 0.03983 = 0.04022 0.00869 -0.00117 -0.00377 H7 2 0.557603 0.341030 0.372295 11.00000 -1.50000 C1 1 0.289473 0.521934 0.298787 11.00000 0.02798 0.01914 = 0.03384 0.00040 0.00091 -0.00623 AFIX 23 H6 2 0.381403 0.573543 0.317220 11.00000 -1.20000 H1 2 0.179628 0.543756 0.331837 11.00000 -1.20000 AFIX 0 C2 1 0.340220 0.409272 0.330494 11.00000 0.02191 0.02389 = 0.02928 0.00143 0.00160 -0.00227 AFIX 13 H8 2 0.300558 0.394434 0.401621 11.00000 -1.20000 AFIX 0 C3 1 0.249663 0.331987 0.253869 11.00000 0.02261 0.01741 = 0.02605 0.00238 0.00221 0.00235 C4 1 0.075776 0.283894 0.294725 11.00000 0.02648 0.01220 = 0.03186 0.00178 -0.00063 -0.00121 AFIX 13 H22 2 0.094022 0.209844 0.320749 11.00000 -1.20000 AFIX 0 C5 1 -0.013449 0.351940 0.373734 11.00000 0.01754 0.02024 = 0.03354 0.00060 0.00274 -0.00512 C6 1 -0.012093 0.321771 0.481104 11.00000 0.02344 0.03032 = 0.03387 0.00162 0.00474 -0.00495 AFIX 43 H2 2 -0.078454 0.363642 0.527111 11.00000 -1.20000 AFIX 0 C7 1 0.192489 0.403985 0.159895 11.00000 0.02580 0.01805 = 0.02803 0.00199 0.00222 0.00133 C8 1 0.266973 0.366611 0.057582 11.00000 0.04066 0.03461 = 0.03020 0.00199 0.00541 0.00744 AFIX 137 H4 2 0.236048 0.417884 0.004284 11.00000 -1.50000 H3 2 0.218900 0.296564 0.040476 11.00000 -1.50000 H5 2 0.393551 0.361509 0.062631 11.00000 -1.50000 AFIX 0 C9 1 0.267727 0.515366 0.183076 11.00000 0.02396 0.02124 = 0.03408 0.00776 0.00286 -0.00275 AFIX 23 H9 2 0.381085 0.524671 0.148756 11.00000 -1.20000 H10 2 0.187743 0.571647 0.158845 11.00000 -1.20000 AFIX 0 C10 1 -0.013190 0.397696 0.159832 11.00000 0.02820 0.01969 = 0.03173 0.00514 -0.00679 -0.00199 C11 1 -0.104616 0.473448 0.235237 11.00000 0.02246 0.02012 = 0.04441 0.00543 -0.00085 0.00033 AFIX 23 H12 2 -0.051674 0.545014 0.228857 11.00000 -1.20000 H11 2 -0.227943 0.479776 0.215064 11.00000 -1.20000 AFIX 0 C12 1 -0.097062 0.440417 0.344709 11.00000 0.02331 0.02244 = 0.03894 -0.00111 0.00720 -0.00099 AFIX 43 H13 2 -0.152795 0.483148 0.394683 11.00000 -1.20000 AFIX 0 C13 1 -0.039861 0.283270 0.199558 11.00000 0.03371 0.01847 = 0.03568 0.00067 -0.00614 -0.00512 AFIX 23 H15 2 -0.162786 0.269651 0.217114 11.00000 -1.20000 H14 2 -0.000431 0.229625 0.149344 11.00000 -1.20000 AFIX 0 C14 1 -0.093722 0.416649 0.054758 11.00000 0.03831 0.03725 = 0.03760 0.00700 -0.01171 -0.00569 AFIX 137 H17 2 -0.048678 0.363849 0.006531 11.00000 -1.50000 H16 2 -0.063904 0.488412 0.031085 11.00000 -1.50000 H18 2 -0.220127 0.409816 0.059409 11.00000 -1.50000 AFIX 0 C15 1 0.368922 0.238467 0.227555 11.00000 0.03357 0.02479 = 0.03530 0.00194 0.00454 0.01098 AFIX 137 H20 2 0.473924 0.265316 0.194192 11.00000 -1.50000 H19 2 0.308324 0.189549 0.181510 11.00000 -1.50000 H21 2 0.400894 0.200645 0.290110 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_llg14_0m in P2(1)2(1)2(1) REM R1 = 0.0513 for 2295 Fo > 4sig(Fo) and 0.0513 for all 2306 data REM 161 parameters refined using 0 restraints END WGHT 0.1009 0.1800 REM Instructions for potential hydrogen bonds HTAB O2 O1_$1 REM Highest difference peak 0.292, deepest hole -0.319, 1-sigma level 0.060 Q1 1 -0.0346 0.3421 0.1790 11.00000 0.05 0.29 Q2 1 0.2789 0.3720 0.2898 11.00000 0.05 0.26 Q3 1 0.3152 0.2885 0.2361 11.00000 0.05 0.25 Q4 1 0.2276 0.3649 0.2062 11.00000 0.05 0.25 ; _shelx_res_checksum 15477 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_cu_llg9_0m _database_code_depnum_ccdc_archive 'CCDC 1851594' loop_ _audit_author_name _audit_author_address 'Xiao-Nian Li' ;Kunming Institute of Botany, Chinese Academy of Sciences China ; _audit_update_record ; 2018-06-26 deposited with the CCDC. 2019-11-04 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 O4' _chemical_formula_sum 'C16 H24 O4' _chemical_formula_weight 280.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _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+1/2, -z' _cell_length_a 6.4948(2) _cell_length_b 7.4524(3) _cell_length_c 15.2812(6) _cell_angle_alpha 90 _cell_angle_beta 101.0040(10) _cell_angle_gamma 90 _cell_volume 726.04(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7484 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 70.09 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_F_000 304 _exptl_transmission_factor_min 0.3130 _exptl_transmission_factor_max 0.5220 _exptl_crystal_size_max 0.640 _exptl_crystal_size_mid 0.420 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 0.736 _shelx_estimated_absorpt_T_min 0.650 _shelx_estimated_absorpt_T_max 0.930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details sadabs _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7540 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.946 _diffrn_reflns_theta_max 70.141 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.933 _diffrn_measured_fraction_theta_full 0.948 _diffrn_reflns_Laue_measured_fraction_max 0.933 _diffrn_reflns_Laue_measured_fraction_full 0.948 _diffrn_reflns_point_group_measured_fraction_max 0.916 _diffrn_reflns_point_group_measured_fraction_full 0.937 _reflns_number_total 2510 _reflns_number_gt 2499 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.815 _reflns_Friedel_fraction_max 0.896 _reflns_Friedel_fraction_full 0.924 _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 APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _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^)+(0.0597P)^2^+0.1084P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1119 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.17(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 2510 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 O1 O 0.5846(2) 0.1316(2) 0.59832(9) 0.0181(3) Uani 1 1 d . . . . . H1 H 0.536(4) 0.028(5) 0.5987(18) 0.027 Uiso 1 1 d . U . . . O2 O 0.9229(2) 0.7489(2) 0.85996(9) 0.0222(3) Uani 1 1 d . . . . . O3 O 0.4502(2) 0.76548(18) 0.57251(9) 0.0174(3) Uani 1 1 d . . . . . H12 H 0.427(4) 0.735(4) 0.5175(19) 0.026 Uiso 1 1 d . U . . . O4 O 0.6740(3) 0.7129(4) 0.94034(11) 0.0595(7) Uani 1 1 d . . . . . C1 C 0.5797(3) 0.2281(3) 0.67857(12) 0.0138(4) Uani 1 1 d . . . . . H24 H 0.6816 0.3296 0.6817 0.017 Uiso 1 1 calc R U . . . C2 C 0.3622(3) 0.3103(2) 0.68590(11) 0.0130(4) Uani 1 1 d . . . . . C3 C 0.3883(3) 0.3457(3) 0.79015(12) 0.0153(4) Uani 1 1 d . . . . . C4 C 0.3866(3) 0.5540(3) 0.79626(12) 0.0159(4) Uani 1 1 d . . . . . H10 H 0.3413 0.5953 0.8519 0.019 Uiso 1 1 calc R U . . . C5 C 0.5932(3) 0.6371(2) 0.78706(12) 0.0147(4) Uani 1 1 d . . . . . C6 C 0.7305(3) 0.7020(3) 0.87077(13) 0.0210(4) Uani 1 1 d . . . . . C7 C 1.0575(4) 0.8213(3) 0.93788(14) 0.0283(5) Uani 1 1 d . . . . . H20 H 0.9911 0.9272 0.9586 0.042 Uiso 1 1 calc R U . . . H2 H 1.1923 0.8555 0.9230 0.042 Uiso 1 1 calc R U . . . H19 H 1.0805 0.7304 0.9851 0.042 Uiso 1 1 calc R U . . . C8 C 0.2086(3) 0.2727(3) 0.83232(13) 0.0232(4) Uani 1 1 d . . . . . H3 H 0.1986 0.1424 0.8240 0.035 Uiso 1 1 calc R U . . . H5 H 0.0764 0.3287 0.8037 0.035 Uiso 1 1 calc R U . . . H4 H 0.2364 0.3004 0.8962 0.035 Uiso 1 1 calc R U . . . C9 C 0.5946(3) 0.2506(3) 0.83443(12) 0.0177(4) Uani 1 1 d . . . . . H9 H 0.7100 0.3385 0.8503 0.021 Uiso 1 1 calc R U . . . H6 H 0.5760 0.1861 0.8890 0.021 Uiso 1 1 calc R U . . . C10 C 0.6411(3) 0.1192(3) 0.76398(13) 0.0174(4) Uani 1 1 d . . . . . H8 H 0.7914 0.0860 0.7748 0.021 Uiso 1 1 calc R U . . . H7 H 0.5553 0.0091 0.7622 0.021 Uiso 1 1 calc R U . . . C11 C 0.6454(3) 0.6586(2) 0.70751(12) 0.0143(4) Uani 1 1 d . . . . . H11 H 0.7770 0.7111 0.7043 0.017 Uiso 1 1 calc R U . . . C12 C 0.5026(3) 0.6024(2) 0.62263(12) 0.0139(4) Uani 1 1 d . . . . . H18 H 0.5822 0.5220 0.5886 0.017 Uiso 1 1 calc R U . . . C13 C 0.3054(3) 0.5005(3) 0.64007(12) 0.0143(4) Uani 1 1 d . . . . . C14 C 0.2245(3) 0.6033(3) 0.71318(12) 0.0176(4) Uani 1 1 d . . . . . H14 H 0.0822 0.5630 0.7185 0.021 Uiso 1 1 calc R U . . . H13 H 0.2223 0.7342 0.7020 0.021 Uiso 1 1 calc R U . . . C15 C 0.1427(3) 0.4941(3) 0.55302(12) 0.0202(4) Uani 1 1 d . . . . . H15 H 0.0135 0.4383 0.5642 0.030 Uiso 1 1 calc R U . . . H17 H 0.1983 0.4235 0.5086 0.030 Uiso 1 1 calc R U . . . H16 H 0.1124 0.6164 0.5306 0.030 Uiso 1 1 calc R U . . . C16 C 0.1935(3) 0.1699(3) 0.65168(12) 0.0184(4) Uani 1 1 d . . . . . H22 H 0.1895 0.1481 0.5881 0.028 Uiso 1 1 calc R U . . . H23 H 0.0565 0.2141 0.6601 0.028 Uiso 1 1 calc R U . . . H21 H 0.2267 0.0578 0.6849 0.028 Uiso 1 1 calc R 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 O1 0.0273(7) 0.0146(7) 0.0131(7) -0.0015(5) 0.0058(5) -0.0008(5) O2 0.0234(7) 0.0248(7) 0.0158(7) -0.0048(6) -0.0029(5) -0.0009(6) O3 0.0266(7) 0.0135(7) 0.0114(6) 0.0019(5) 0.0019(5) 0.0001(5) O4 0.0591(12) 0.106(2) 0.0172(9) -0.0244(10) 0.0156(8) -0.0474(13) C1 0.0168(8) 0.0126(9) 0.0118(9) -0.0007(7) 0.0021(6) 0.0000(7) C2 0.0162(9) 0.0132(9) 0.0099(8) 0.0014(7) 0.0034(6) -0.0004(7) C3 0.0190(9) 0.0176(10) 0.0094(8) -0.0003(7) 0.0031(6) -0.0027(7) C4 0.0207(9) 0.0172(10) 0.0114(9) -0.0008(7) 0.0070(7) 0.0016(7) C5 0.0218(9) 0.0111(9) 0.0113(9) -0.0006(7) 0.0034(7) 0.0011(7) C6 0.0322(10) 0.0182(10) 0.0123(10) -0.0017(7) 0.0036(8) -0.0044(8) C7 0.0343(11) 0.0274(12) 0.0195(10) -0.0042(8) -0.0040(8) -0.0064(9) C8 0.0259(10) 0.0293(12) 0.0165(10) 0.0040(8) 0.0095(7) -0.0049(8) C9 0.0235(9) 0.0168(9) 0.0112(9) 0.0030(7) -0.0007(7) 0.0000(8) C10 0.0210(9) 0.0154(9) 0.0144(9) 0.0025(7) -0.0005(7) 0.0015(7) C11 0.0167(8) 0.0105(9) 0.0151(9) 0.0003(7) 0.0016(7) 0.0012(7) C12 0.0177(8) 0.0130(9) 0.0113(9) 0.0008(7) 0.0035(7) 0.0003(7) C13 0.0145(8) 0.0148(9) 0.0132(9) 0.0017(7) 0.0016(7) 0.0005(7) C14 0.0173(8) 0.0174(10) 0.0190(10) 0.0018(7) 0.0059(7) 0.0033(7) C15 0.0186(9) 0.0232(10) 0.0168(10) 0.0051(8) -0.0014(7) -0.0006(7) C16 0.0186(9) 0.0195(10) 0.0164(9) 0.0010(7) 0.0012(7) -0.0041(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.427(2) . ? O1 H1 0.84(3) . ? O2 C6 1.338(3) . ? O2 C7 1.441(2) . ? O3 C12 1.442(2) . ? O3 H12 0.86(3) . ? O4 C6 1.192(3) . ? C1 C10 1.524(2) . ? C1 C2 1.563(2) . ? C1 H24 1.0000 . ? C2 C16 1.533(2) . ? C2 C3 1.592(2) . ? C2 C13 1.592(2) . ? C3 C8 1.536(3) . ? C3 C9 1.552(3) . ? C3 C4 1.556(3) . ? C4 C5 1.509(3) . ? C4 C14 1.531(2) . ? C4 H10 1.0000 . ? C5 C11 1.332(3) . ? C5 C6 1.493(2) . ? C7 H20 0.9800 . ? C7 H2 0.9800 . ? C7 H19 0.9800 . ? C8 H3 0.9800 . ? C8 H5 0.9800 . ? C8 H4 0.9800 . ? C9 C10 1.527(3) . ? C9 H9 0.9900 . ? C9 H6 0.9900 . ? C10 H8 0.9900 . ? C10 H7 0.9900 . ? C11 C12 1.503(2) . ? C11 H11 0.9500 . ? C12 C13 1.555(2) . ? C12 H18 1.0000 . ? C13 C14 1.528(3) . ? C13 C15 1.534(2) . ? C14 H14 0.9900 . ? C14 H13 0.9900 . ? C15 H15 0.9800 . ? C15 H17 0.9800 . ? C15 H16 0.9800 . ? C16 H22 0.9800 . ? C16 H23 0.9800 . ? C16 H21 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 C1 O1 H1 113.0(19) . . ? C6 O2 C7 115.43(16) . . ? C12 O3 H12 106(2) . . ? O1 C1 C10 115.00(16) . . ? O1 C1 C2 115.33(14) . . ? C10 C1 C2 103.88(14) . . ? O1 C1 H24 107.4 . . ? C10 C1 H24 107.4 . . ? C2 C1 H24 107.4 . . ? C16 C2 C1 107.73(15) . . ? C16 C2 C3 112.78(15) . . ? C1 C2 C3 102.21(13) . . ? C16 C2 C13 111.54(14) . . ? C1 C2 C13 116.99(14) . . ? C3 C2 C13 105.33(14) . . ? C8 C3 C9 108.49(16) . . ? C8 C3 C4 108.27(16) . . ? C9 C3 C4 116.42(15) . . ? C8 C3 C2 114.64(15) . . ? C9 C3 C2 106.20(15) . . ? C4 C3 C2 102.99(14) . . ? C5 C4 C14 107.89(15) . . ? C5 C4 C3 112.79(15) . . ? C14 C4 C3 101.61(15) . . ? C5 C4 H10 111.4 . . ? C14 C4 H10 111.4 . . ? C3 C4 H10 111.4 . . ? C11 C5 C6 121.91(18) . . ? C11 C5 C4 121.31(17) . . ? C6 C5 C4 116.70(16) . . ? O4 C6 O2 123.09(19) . . ? O4 C6 C5 123.5(2) . . ? O2 C6 C5 113.44(17) . . ? O2 C7 H20 109.5 . . ? O2 C7 H2 109.5 . . ? H20 C7 H2 109.5 . . ? O2 C7 H19 109.5 . . ? H20 C7 H19 109.5 . . ? H2 C7 H19 109.5 . . ? C3 C8 H3 109.5 . . ? C3 C8 H5 109.5 . . ? H3 C8 H5 109.5 . . ? C3 C8 H4 109.5 . . ? H3 C8 H4 109.5 . . ? H5 C8 H4 109.5 . . ? C10 C9 C3 104.82(14) . . ? C10 C9 H9 110.8 . . ? C3 C9 H9 110.8 . . ? C10 C9 H6 110.8 . . ? C3 C9 H6 110.8 . . ? H9 C9 H6 108.9 . . ? C1 C10 C9 102.00(15) . . ? C1 C10 H8 111.4 . . ? C9 C10 H8 111.4 . . ? C1 C10 H7 111.4 . . ? C9 C10 H7 111.4 . . ? H8 C10 H7 109.2 . . ? C5 C11 C12 122.11(17) . . ? C5 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? O3 C12 C11 105.52(14) . . ? O3 C12 C13 112.59(14) . . ? C11 C12 C13 112.39(15) . . ? O3 C12 H18 108.7 . . ? C11 C12 H18 108.7 . . ? C13 C12 H18 108.7 . . ? C14 C13 C15 111.93(15) . . ? C14 C13 C12 106.84(15) . . ? C15 C13 C12 108.67(14) . . ? C14 C13 C2 101.99(14) . . ? C15 C13 C2 114.66(15) . . ? C12 C13 C2 112.40(14) . . ? C13 C14 C4 102.01(14) . . ? C13 C14 H14 111.4 . . ? C4 C14 H14 111.4 . . ? C13 C14 H13 111.4 . . ? C4 C14 H13 111.4 . . ? H14 C14 H13 109.2 . . ? C13 C15 H15 109.5 . . ? C13 C15 H17 109.5 . . ? H15 C15 H17 109.5 . . ? C13 C15 H16 109.5 . . ? H15 C15 H16 109.5 . . ? H17 C15 H16 109.5 . . ? C2 C16 H22 109.5 . . ? C2 C16 H23 109.5 . . ? H22 C16 H23 109.5 . . ? C2 C16 H21 109.5 . . ? H22 C16 H21 109.5 . . ? H23 C16 H21 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 O1 C1 C2 C16 42.42(19) . . . . ? C10 C1 C2 C16 -84.35(17) . . . . ? O1 C1 C2 C3 161.44(15) . . . . ? C10 C1 C2 C3 34.67(17) . . . . ? O1 C1 C2 C13 -84.12(19) . . . . ? C10 C1 C2 C13 149.10(15) . . . . ? C16 C2 C3 C8 -14.7(2) . . . . ? C1 C2 C3 C8 -130.09(17) . . . . ? C13 C2 C3 C8 107.17(17) . . . . ? C16 C2 C3 C9 105.08(17) . . . . ? C1 C2 C3 C9 -10.32(18) . . . . ? C13 C2 C3 C9 -133.05(15) . . . . ? C16 C2 C3 C4 -132.07(16) . . . . ? C1 C2 C3 C4 112.54(15) . . . . ? C13 C2 C3 C4 -10.20(17) . . . . ? C8 C3 C4 C5 160.14(15) . . . . ? C9 C3 C4 C5 37.7(2) . . . . ? C2 C3 C4 C5 -78.08(17) . . . . ? C8 C3 C4 C14 -84.61(17) . . . . ? C9 C3 C4 C14 152.90(15) . . . . ? C2 C3 C4 C14 37.17(17) . . . . ? C14 C4 C5 C11 -31.8(2) . . . . ? C3 C4 C5 C11 79.6(2) . . . . ? C14 C4 C5 C6 145.21(17) . . . . ? C3 C4 C5 C6 -103.38(19) . . . . ? C7 O2 C6 O4 -2.4(3) . . . . ? C7 O2 C6 C5 176.88(17) . . . . ? C11 C5 C6 O4 166.8(2) . . . . ? C4 C5 C6 O4 -10.2(3) . . . . ? C11 C5 C6 O2 -12.5(3) . . . . ? C4 C5 C6 O2 170.52(16) . . . . ? C8 C3 C9 C10 106.20(17) . . . . ? C4 C3 C9 C10 -131.43(17) . . . . ? C2 C3 C9 C10 -17.50(19) . . . . ? O1 C1 C10 C9 -173.41(14) . . . . ? C2 C1 C10 C9 -46.43(17) . . . . ? C3 C9 C10 C1 39.21(18) . . . . ? C6 C5 C11 C12 -176.69(16) . . . . ? C4 C5 C11 C12 0.2(3) . . . . ? C5 C11 C12 O3 116.82(18) . . . . ? C5 C11 C12 C13 -6.2(2) . . . . ? O3 C12 C13 C14 -75.26(17) . . . . ? C11 C12 C13 C14 43.73(19) . . . . ? O3 C12 C13 C15 45.7(2) . . . . ? C11 C12 C13 C15 164.67(15) . . . . ? O3 C12 C13 C2 173.67(14) . . . . ? C11 C12 C13 C2 -67.34(19) . . . . ? C16 C2 C13 C14 102.20(16) . . . . ? C1 C2 C13 C14 -133.15(15) . . . . ? C3 C2 C13 C14 -20.46(17) . . . . ? C16 C2 C13 C15 -19.0(2) . . . . ? C1 C2 C13 C15 105.68(17) . . . . ? C3 C2 C13 C15 -141.64(15) . . . . ? C16 C2 C13 C12 -143.73(15) . . . . ? C1 C2 C13 C12 -19.1(2) . . . . ? C3 C2 C13 C12 93.60(17) . . . . ? C15 C13 C14 C4 167.24(16) . . . . ? C12 C13 C14 C4 -73.93(17) . . . . ? C2 C13 C14 C4 44.19(17) . . . . ? C5 C4 C14 C13 67.10(18) . . . . ? C3 C4 C14 C13 -51.71(17) . . . . ? 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 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545 O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656 _refine_diff_density_max 0.217 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.057 _shelx_res_file ; cu_llg9_0m.res created by SHELXL-2014/7 TITL cu_llg9_0m in P2(1) CELL 1.54178 6.4948 7.4524 15.2812 90.000 101.004 90.000 ZERR 2.00 0.0002 0.0003 0.0006 0.000 0.001 0.000 LATT -1 SYMM -x, y+1/2, -z SFAC C H O UNIT 32 48 8 L.S. 10 ACTA BOND $H FMAP 2 PLAN -4 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 SIZE 0.100 0.420 0.640 HTAB CONF EQIV $1 x, y-1, z HTAB O1 O3_$1 EQIV $2 -x+1, y+1/2, -z+1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 HTAB O1 O3_$1 HTAB O3 O1_$2 TEMP -173.000 WGHT 0.059700 0.108400 FVAR 0.39485 O1 3 0.584613 0.131615 0.598316 11.00000 0.02734 0.01458 = 0.01309 -0.00149 0.00582 -0.00081 H1 2 0.536348 0.027557 0.598725 11.00000 -1.50000 O2 3 0.922903 0.748945 0.859957 11.00000 0.02344 0.02483 = 0.01580 -0.00481 -0.00286 -0.00089 O3 3 0.450224 0.765478 0.572507 11.00000 0.02656 0.01354 = 0.01141 0.00188 0.00190 0.00011 H12 2 0.426910 0.734913 0.517547 11.00000 -1.50000 O4 3 0.674041 0.712901 0.940341 11.00000 0.05906 0.10560 = 0.01723 -0.02440 0.01559 -0.04737 C1 1 0.579669 0.228090 0.678567 11.00000 0.01680 0.01263 = 0.01177 -0.00070 0.00205 0.00002 AFIX 13 H24 2 0.681556 0.329566 0.681697 11.00000 -1.20000 AFIX 0 C2 1 0.362190 0.310319 0.685896 11.00000 0.01622 0.01316 = 0.00991 0.00138 0.00338 -0.00041 C3 1 0.388312 0.345684 0.790150 11.00000 0.01902 0.01765 = 0.00943 -0.00033 0.00314 -0.00266 C4 1 0.386577 0.554019 0.796256 11.00000 0.02067 0.01718 = 0.01144 -0.00081 0.00698 0.00162 AFIX 13 H10 2 0.341283 0.595251 0.851919 11.00000 -1.20000 AFIX 0 C5 1 0.593235 0.637131 0.787062 11.00000 0.02179 0.01114 = 0.01134 -0.00060 0.00340 0.00106 C6 1 0.730481 0.702014 0.870769 11.00000 0.03220 0.01817 = 0.01225 -0.00168 0.00357 -0.00442 C7 1 1.057471 0.821302 0.937876 11.00000 0.03429 0.02738 = 0.01954 -0.00417 -0.00402 -0.00639 AFIX 137 H20 2 0.991098 0.927163 0.958581 11.00000 -1.50000 H2 2 1.192329 0.855526 0.922958 11.00000 -1.50000 H19 2 1.080534 0.730441 0.985098 11.00000 -1.50000 AFIX 0 C8 1 0.208647 0.272678 0.832318 11.00000 0.02592 0.02930 = 0.01649 0.00396 0.00949 -0.00486 AFIX 137 H3 2 0.198604 0.142371 0.823967 11.00000 -1.50000 H5 2 0.076362 0.328724 0.803703 11.00000 -1.50000 H4 2 0.236361 0.300367 0.896184 11.00000 -1.50000 AFIX 0 C9 1 0.594632 0.250606 0.834426 11.00000 0.02346 0.01682 = 0.01120 0.00301 -0.00072 0.00001 AFIX 23 H9 2 0.710000 0.338510 0.850319 11.00000 -1.20000 H6 2 0.576013 0.186076 0.889009 11.00000 -1.20000 AFIX 0 C10 1 0.641121 0.119245 0.763980 11.00000 0.02096 0.01541 = 0.01438 0.00246 -0.00054 0.00154 AFIX 23 H8 2 0.791432 0.086018 0.774759 11.00000 -1.20000 H7 2 0.555265 0.009073 0.762242 11.00000 -1.20000 AFIX 0 C11 1 0.645371 0.658604 0.707507 11.00000 0.01671 0.01046 = 0.01514 0.00025 0.00164 0.00124 AFIX 43 H11 2 0.777016 0.711145 0.704339 11.00000 -1.20000 AFIX 0 C12 1 0.502617 0.602377 0.622633 11.00000 0.01773 0.01302 = 0.01126 0.00078 0.00349 0.00026 AFIX 13 H18 2 0.582229 0.522007 0.588559 11.00000 -1.20000 AFIX 0 C13 1 0.305448 0.500452 0.640075 11.00000 0.01448 0.01477 = 0.01319 0.00170 0.00163 0.00054 C14 1 0.224544 0.603288 0.713179 11.00000 0.01726 0.01743 = 0.01904 0.00176 0.00593 0.00328 AFIX 23 H14 2 0.082189 0.562988 0.718471 11.00000 -1.20000 H13 2 0.222264 0.734201 0.702032 11.00000 -1.20000 AFIX 0 C15 1 0.142740 0.494083 0.553020 11.00000 0.01861 0.02316 = 0.01682 0.00513 -0.00139 -0.00058 AFIX 137 H15 2 0.013541 0.438335 0.564176 11.00000 -1.50000 H17 2 0.198274 0.423493 0.508629 11.00000 -1.50000 H16 2 0.112433 0.616351 0.530626 11.00000 -1.50000 AFIX 0 C16 1 0.193514 0.169889 0.651678 11.00000 0.01864 0.01945 = 0.01638 0.00101 0.00122 -0.00410 AFIX 137 H22 2 0.189508 0.148067 0.588133 11.00000 -1.50000 H23 2 0.056537 0.214058 0.660135 11.00000 -1.50000 H21 2 0.226668 0.057769 0.684891 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_llg9_0m in P2(1) REM R1 = 0.0327 for 2499 Fo > 4sig(Fo) and 0.0327 for all 2510 data REM 191 parameters refined using 1 restraints END WGHT 0.0595 0.1113 REM Instructions for potential hydrogen bonds HTAB O1 O3_$1 HTAB O3 O1_$2 REM Highest difference peak 0.217, deepest hole -0.260, 1-sigma level 0.057 Q1 1 0.6118 0.1656 0.7225 11.00000 0.05 0.22 Q2 1 0.5819 0.6268 0.6631 11.00000 0.05 0.19 Q3 1 0.7270 0.6324 0.9203 11.00000 0.05 0.17 Q4 1 0.0495 0.9278 0.6228 11.00000 0.05 0.17 ; _shelx_res_checksum 32531