data_exp_2488 _audit_creation_date 2013-11-18 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H18 O3' _chemical_formula_sum 'C18 H18 O3' _chemical_formula_weight 282.32 _chemical_melting_point ? _chemical_oxdiff_formula C18H18O3 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.9757(10) _cell_length_b 14.2207(12) _cell_length_c 7.4940(6) _cell_angle_alpha 90 _cell_angle_beta 97.598(8) _cell_angle_gamma 90 _cell_volume 1476.3(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2203 _cell_measurement_temperature 180.00(10) _cell_measurement_theta_max 26.3500 _cell_measurement_theta_min 4.0250 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour '' _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description '' _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0363 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 5792 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_min 3.094 _diffrn_ambient_temperature 180.00(10) _diffrn_detector_area_resol_mean 10.3914 _diffrn_measured_fraction_theta_full 0.9892 _diffrn_measured_fraction_theta_max 0.8343 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -52.00 28.00 1.0000 1.6100 omega____ theta____ kappa____ phi______ frames - 10.8579 -38.0000 -120.0000 80 #__ type_ start__ end____ width___ exp.time_ 2 omega -6.00 82.00 1.0000 1.6100 omega____ theta____ kappa____ phi______ frames - 10.8579 38.0000 60.0000 88 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0172018000 _diffrn_orient_matrix_UB_12 0.0443393000 _diffrn_orient_matrix_UB_13 0.0251647000 _diffrn_orient_matrix_UB_21 -0.0136981000 _diffrn_orient_matrix_UB_22 0.0113555000 _diffrn_orient_matrix_UB_23 -0.0919603000 _diffrn_orient_matrix_UB_31 -0.0462793000 _diffrn_orient_matrix_UB_32 -0.0198567000 _diffrn_orient_matrix_UB_33 0.0037353000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2186 _reflns_number_total 2891 _reflns_odcompleteness_completeness 98.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.97 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.131 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 2891 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0441 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.2651P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.1171 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18) 2.c Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C12(H12A,H12B,H12C) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary ? 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 0.70115(11) 0.54355(11) 0.6949(2) 0.0323(4) Uani 1 1 d . . . . . C2 C 0.75644(12) 0.54786(12) 0.8865(2) 0.0379(4) Uani 1 1 d . . . . . H2A H 0.8001 0.6029 0.9007 0.045 Uiso 1 1 calc R U . . . H2B H 0.7113 0.5515 0.9775 0.045 Uiso 1 1 calc R U . . . C3 C 0.81267(11) 0.45776(12) 0.9045(2) 0.0352(4) Uani 1 1 d . . . . . C4 C 0.89441(12) 0.43606(14) 1.0223(2) 0.0426(4) Uani 1 1 d . . . . . H4 H 0.9202 0.4798 1.1117 0.051 Uiso 1 1 calc R U . . . C5 C 0.93804(12) 0.34937(15) 1.0078(3) 0.0474(5) Uani 1 1 d . . . . . H5 H 0.9950 0.3341 1.0862 0.057 Uiso 1 1 calc R U . . . C6 C 0.89958(12) 0.28540(14) 0.8807(3) 0.0458(5) Uani 1 1 d . . . . . H6 H 0.9298 0.2260 0.8734 0.055 Uiso 1 1 calc R U . . . C7 C 0.81700(11) 0.30635(12) 0.7624(2) 0.0384(4) Uani 1 1 d . . . . . H7 H 0.7903 0.2618 0.6751 0.046 Uiso 1 1 calc R U . . . C8 C 0.77474(11) 0.39349(11) 0.7751(2) 0.0320(4) Uani 1 1 d . . . . . C9 C 0.68816(10) 0.43323(11) 0.6563(2) 0.0319(4) Uani 1 1 d . . . . . C10 C 0.68189(12) 0.40630(12) 0.4587(2) 0.0399(4) Uani 1 1 d . . . . . H10A H 0.7435 0.4202 0.4151 0.060 Uiso 1 1 calc R U . . . H10B H 0.6302 0.4424 0.3886 0.060 Uiso 1 1 calc R U . . . H10C H 0.6679 0.3390 0.4449 0.060 Uiso 1 1 calc R U . . . C11 C 0.59365(11) 0.40394(11) 0.7222(2) 0.0368(4) Uani 1 1 d . . . . . C12 C 0.51440(14) 0.36127(18) 0.9682(3) 0.0648(6) Uani 1 1 d . . . . . H12A H 0.4660 0.4110 0.9413 0.097 Uiso 1 1 calc R U . . . H12B H 0.5282 0.3528 1.0988 0.097 Uiso 1 1 calc R U . . . H12C H 0.4896 0.3023 0.9123 0.097 Uiso 1 1 calc R U . . . C13 C 0.75927(11) 0.58855(11) 0.5582(2) 0.0328(4) Uani 1 1 d . . . . . C14 C 0.71496(12) 0.64686(12) 0.4236(2) 0.0384(4) Uani 1 1 d . . . . . H14 H 0.6478 0.6591 0.4172 0.046 Uiso 1 1 calc R U . . . C15 C 0.76639(14) 0.68752(13) 0.2988(2) 0.0466(5) Uani 1 1 d . . . . . H15 H 0.7344 0.7274 0.2082 0.056 Uiso 1 1 calc R U . . . C16 C 0.86345(14) 0.67071(13) 0.3044(3) 0.0500(5) Uani 1 1 d . . . . . H16 H 0.8986 0.6984 0.2178 0.060 Uiso 1 1 calc R U . . . C17 C 0.90953(13) 0.61310(14) 0.4372(3) 0.0474(5) Uani 1 1 d . . . . . H17 H 0.9767 0.6012 0.4423 0.057 Uiso 1 1 calc R U . . . C18 C 0.85811(12) 0.57267(12) 0.5629(3) 0.0409(4) Uani 1 1 d . . . . . H18 H 0.8906 0.5334 0.6540 0.049 Uiso 1 1 calc R U . . . O1 O 0.61134(8) 0.58964(8) 0.69864(16) 0.0400(3) Uani 1 1 d . . . . . H1 H 0.5771 0.5833 0.5985 0.060 Uiso 1 1 calc R U . . . O2 O 0.51818(8) 0.39566(10) 0.62591(18) 0.0565(4) Uani 1 1 d . . . . . O3 O 0.60229(8) 0.38758(9) 0.89741(17) 0.0482(4) Uani 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 C1 0.0301(8) 0.0368(8) 0.0304(9) -0.0015(7) 0.0059(7) 0.0032(7) C2 0.0401(9) 0.0428(9) 0.0309(9) -0.0039(8) 0.0057(7) -0.0012(8) C3 0.0317(8) 0.0439(9) 0.0307(9) 0.0023(8) 0.0071(7) -0.0030(7) C4 0.0361(9) 0.0569(11) 0.0341(10) 0.0056(9) 0.0025(7) -0.0059(8) C5 0.0336(9) 0.0660(12) 0.0423(11) 0.0164(10) 0.0045(8) 0.0041(9) C6 0.0406(10) 0.0507(11) 0.0486(12) 0.0127(9) 0.0153(9) 0.0111(9) C7 0.0365(9) 0.0421(9) 0.0388(10) 0.0024(8) 0.0125(8) 0.0002(8) C8 0.0279(8) 0.0390(9) 0.0305(9) 0.0020(7) 0.0090(7) -0.0015(7) C9 0.0280(8) 0.0372(8) 0.0307(9) -0.0009(7) 0.0047(7) -0.0019(7) C10 0.0446(10) 0.0410(9) 0.0338(10) -0.0038(8) 0.0046(8) -0.0050(8) C11 0.0323(9) 0.0387(9) 0.0394(10) 0.0034(8) 0.0055(8) -0.0008(7) C12 0.0468(11) 0.0936(16) 0.0590(14) 0.0104(13) 0.0258(10) -0.0084(11) C13 0.0339(8) 0.0344(8) 0.0304(9) -0.0073(7) 0.0054(7) -0.0049(7) C14 0.0393(9) 0.0403(9) 0.0356(10) -0.0019(8) 0.0050(7) -0.0072(8) C15 0.0574(11) 0.0454(10) 0.0366(10) 0.0024(8) 0.0049(9) -0.0147(9) C16 0.0582(12) 0.0537(11) 0.0415(11) -0.0075(9) 0.0192(9) -0.0239(10) C17 0.0388(10) 0.0552(11) 0.0508(12) -0.0113(10) 0.0161(9) -0.0126(9) C18 0.0361(9) 0.0456(10) 0.0418(11) -0.0037(8) 0.0084(8) -0.0049(8) O1 0.0349(6) 0.0490(7) 0.0373(7) -0.0005(6) 0.0095(5) 0.0082(5) O2 0.0329(7) 0.0804(10) 0.0541(9) 0.0181(7) -0.0023(6) -0.0124(6) O3 0.0355(6) 0.0736(9) 0.0374(7) 0.0044(6) 0.0125(5) -0.0054(6) _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 C2 1.540(2) . ? C1 C9 1.601(2) . ? C1 C13 1.529(2) . ? C1 O1 1.4196(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.500(2) . ? C3 C4 1.383(2) . ? C3 C8 1.386(2) . ? C4 H4 0.9500 . ? C4 C5 1.386(3) . ? C5 H5 0.9500 . ? C5 C6 1.374(3) . ? C6 H6 0.9500 . ? C6 C7 1.391(2) . ? C7 H7 0.9500 . ? C7 C8 1.381(2) . ? C8 C9 1.514(2) . ? C9 C10 1.521(2) . ? C9 C11 1.528(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O2 1.2022(19) . ? C11 O3 1.323(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12 O3 1.450(2) . ? C13 C14 1.387(2) . ? C13 C18 1.395(2) . ? C14 H14 0.9500 . ? C14 C15 1.380(2) . ? C15 H15 0.9500 . ? C15 C16 1.373(3) . ? C16 H16 0.9500 . ? C16 C17 1.381(3) . ? C17 H17 0.9500 . ? C17 C18 1.383(2) . ? C18 H18 0.9500 . ? O1 H1 0.8400 . ? 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 C1 C9 103.78(13) . . ? C13 C1 C2 111.27(13) . . ? C13 C1 C9 110.29(13) . . ? O1 C1 C2 107.41(13) . . ? O1 C1 C9 112.12(12) . . ? O1 C1 C13 111.68(13) . . ? C1 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C3 C2 C1 104.00(13) . . ? C3 C2 H2A 111.0 . . ? C3 C2 H2B 111.0 . . ? C4 C3 C2 128.79(16) . . ? C4 C3 C8 120.45(16) . . ? C8 C3 C2 110.69(14) . . ? C3 C4 H4 120.6 . . ? C3 C4 C5 118.88(18) . . ? C5 C4 H4 120.6 . . ? C4 C5 H5 119.8 . . ? C6 C5 C4 120.50(16) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 119.5 . . ? C5 C6 C7 121.02(17) . . ? C7 C6 H6 119.5 . . ? C6 C7 H7 120.8 . . ? C8 C7 C6 118.32(17) . . ? C8 C7 H7 120.8 . . ? C3 C8 C9 111.55(14) . . ? C7 C8 C3 120.83(15) . . ? C7 C8 C9 127.60(15) . . ? C8 C9 C1 101.36(12) . . ? C8 C9 C10 114.66(13) . . ? C8 C9 C11 111.50(13) . . ? C10 C9 C1 114.38(13) . . ? C10 C9 C11 107.75(13) . . ? C11 C9 C1 106.93(13) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C9 124.08(16) . . ? O2 C11 O3 122.40(15) . . ? O3 C11 C9 113.52(14) . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? C14 C13 C1 120.78(14) . . ? C14 C13 C18 117.43(15) . . ? C18 C13 C1 121.79(15) . . ? C13 C14 H14 119.3 . . ? C15 C14 C13 121.41(16) . . ? C15 C14 H14 119.3 . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.49(18) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 120.3 . . ? C15 C16 C17 119.37(17) . . ? C17 C16 H16 120.3 . . ? C16 C17 H17 119.9 . . ? C16 C17 C18 120.18(17) . . ? C18 C17 H17 119.9 . . ? C13 C18 H18 119.4 . . ? C17 C18 C13 121.13(17) . . ? C17 C18 H18 119.4 . . ? C1 O1 H1 109.5 . . ? C11 O3 C12 115.97(14) . . ? _shelx_estimated_absorpt_T_max 0.991 _shelx_estimated_absorpt_T_min 0.983 _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. ; _shelxl_version_number 2013-3