# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Giridhar U. Kulkarni' _publ_contact_author_email KULKARNI@JNCASR.AC.IN _publ_section_title ; The influence of crystal packing on the solid state fluorescence behavior of alkyloxy substituted phenyleneethynylenes ; loop_ _publ_author_name 'Giridhar U. Kulkarni' 'Reji Thomas' 'Shinto Varghese' # Attachment 'Methoxy.cif' data_tryd _database_code_depnum_ccdc_archive 'CCDC 695299' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 O2' _chemical_formula_weight 338.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.4950(5) _cell_length_b 11.0758(4) _cell_length_c 10.6108(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.3920(10) _cell_angle_gamma 90.00 _cell_volume 1778.59(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 120 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius-Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6893 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1684 _reflns_number_gt 1545 _reflns_threshold_expression >2sigma(I) _computing_data_collection Bruker-Nonius _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (CCDC.cam.ac.uk)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+1.4056P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1684 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C10 C 0.05972(8) 0.02407(11) 0.92196(11) 0.0178(3) Uani 1 1 d . . . C11 C 0.01937(8) 0.11928(10) 0.97203(11) 0.0175(3) Uani 1 1 d . . . C8 C 0.08285(7) -0.19442(11) 0.89521(11) 0.0165(3) Uani 1 1 d . . . C2 C 0.09672(8) -0.43064(11) 0.68200(12) 0.0201(3) Uani 1 1 d . . . C9 C 0.04100(7) -0.09563(11) 0.94910(11) 0.0158(3) Uani 1 1 d . . . C1 C 0.15024(8) -0.37618(11) 0.78999(11) 0.0171(3) Uani 1 1 d . . . C7 C 0.11637(8) -0.27463(11) 0.84998(11) 0.0179(3) Uani 1 1 d . . . O1 O 0.03357(6) 0.23808(8) 0.94906(9) 0.0265(3) Uani 1 1 d . . . C6 C 0.23476(8) -0.42277(12) 0.83851(12) 0.0215(3) Uani 1 1 d . . . C5 C 0.26428(8) -0.52257(12) 0.78138(12) 0.0234(3) Uani 1 1 d . . . C3 C 0.12612(9) -0.53060(12) 0.62534(12) 0.0223(3) Uani 1 1 d . . . C4 C 0.21008(9) -0.57672(12) 0.67503(12) 0.0226(3) Uani 1 1 d . . . C12 C 0.10198(11) 0.26603(13) 0.88182(16) 0.0330(4) Uani 1 1 d . . . H10 H 0.1084(9) 0.0419(12) 0.8687(13) 0.015(3) Uiso 1 1 d . . . H2 H 0.0392(10) -0.3977(13) 0.6468(14) 0.022(4) Uiso 1 1 d . . . H3 H 0.0883(11) -0.5667(15) 0.5533(16) 0.030(4) Uiso 1 1 d . . . H6 H 0.2720(10) -0.3864(14) 0.9126(15) 0.027(4) Uiso 1 1 d . . . H4 H 0.2310(10) -0.6465(15) 0.6345(15) 0.028(4) Uiso 1 1 d . . . H5 H 0.3230(11) -0.5552(14) 0.8162(16) 0.031(4) Uiso 1 1 d . . . H12C H 0.1630(11) 0.2278(15) 0.9305(16) 0.032(4) Uiso 1 1 d . . . H12B H 0.0864(11) 0.2331(15) 0.7910(17) 0.035(4) Uiso 1 1 d . . . H12A H 0.1049(12) 0.3567(18) 0.8842(17) 0.043(5) 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 C10 0.0168(6) 0.0185(6) 0.0186(5) -0.0006(5) 0.0046(4) 0.0003(5) C11 0.0186(6) 0.0135(6) 0.0198(6) 0.0001(4) 0.0027(5) -0.0006(4) C8 0.0144(5) 0.0169(6) 0.0171(5) 0.0009(4) 0.0008(4) -0.0036(4) C2 0.0178(6) 0.0208(6) 0.0216(6) 0.0005(5) 0.0037(5) 0.0026(5) C9 0.0143(6) 0.0158(6) 0.0160(6) -0.0023(4) 0.0002(4) 0.0016(4) C1 0.0188(6) 0.0147(6) 0.0192(6) 0.0002(4) 0.0069(4) 0.0001(4) C7 0.0161(6) 0.0183(6) 0.0190(6) 0.0013(5) 0.0028(4) -0.0029(5) O1 0.0338(5) 0.0150(5) 0.0355(5) 0.0008(4) 0.0181(4) -0.0008(4) C6 0.0195(6) 0.0233(7) 0.0209(6) -0.0026(5) 0.0023(5) 0.0001(5) C5 0.0196(6) 0.0265(7) 0.0245(6) 0.0018(5) 0.0059(5) 0.0073(5) C3 0.0250(6) 0.0210(7) 0.0207(6) -0.0046(5) 0.0045(5) -0.0009(5) C4 0.0277(7) 0.0187(7) 0.0234(6) -0.0015(5) 0.0102(5) 0.0048(5) C12 0.0418(9) 0.0205(7) 0.0436(9) 0.0006(6) 0.0245(7) -0.0053(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 C10 C11 1.3885(17) . ? C10 C9 1.4002(17) . ? C10 H10 1.054(13) . ? C11 O1 1.3646(15) . ? C11 C9 1.4072(16) 5_557 ? C8 C7 1.1816(17) . ? C8 C9 1.4505(16) . ? C2 C3 1.3829(17) . ? C2 C1 1.3988(17) . ? C2 H2 0.961(16) . ? C9 C11 1.4072(16) 5_557 ? C1 C6 1.3989(17) . ? C1 C7 1.4454(16) . ? O1 C12 1.4328(16) . ? C6 C5 1.3848(18) . ? C6 H6 0.959(16) . ? C5 C4 1.3898(19) . ? C5 H5 0.975(17) . ? C3 C4 1.3918(19) . ? C3 H3 0.946(17) . ? C4 H4 0.973(16) . ? C12 H12C 1.063(17) . ? C12 H12B 1.011(18) . ? C12 H12A 1.005(19) . ? 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 C11 C10 C9 120.68(11) . . ? C11 C10 H10 119.7(7) . . ? C9 C10 H10 119.4(7) . . ? O1 C11 C10 124.11(11) . . ? O1 C11 C9 116.04(10) . 5_557 ? C10 C11 C9 119.84(11) . 5_557 ? C7 C8 C9 179.26(13) . . ? C3 C2 C1 120.57(11) . . ? C3 C2 H2 119.9(9) . . ? C1 C2 H2 119.5(9) . . ? C10 C9 C11 119.48(11) . 5_557 ? C10 C9 C8 120.22(10) . . ? C11 C9 C8 120.30(11) 5_557 . ? C2 C1 C6 119.09(11) . . ? C2 C1 C7 119.26(11) . . ? C6 C1 C7 121.64(11) . . ? C8 C7 C1 175.34(12) . . ? C11 O1 C12 117.53(10) . . ? C5 C6 C1 120.29(11) . . ? C5 C6 H6 119.8(9) . . ? C1 C6 H6 119.9(9) . . ? C6 C5 C4 120.07(12) . . ? C6 C5 H5 120.0(10) . . ? C4 C5 H5 120.0(10) . . ? C2 C3 C4 119.84(12) . . ? C2 C3 H3 119.0(10) . . ? C4 C3 H3 121.2(10) . . ? C5 C4 C3 120.13(12) . . ? C5 C4 H4 120.1(9) . . ? C3 C4 H4 119.8(9) . . ? O1 C12 H12C 110.4(9) . . ? O1 C12 H12B 110.2(10) . . ? H12C C12 H12B 109.0(13) . . ? O1 C12 H12A 103.8(10) . . ? H12C C12 H12A 110.8(14) . . ? H12B C12 H12A 112.6(14) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.256 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.040 # Attachment 'Ethoxy.cif' data_tryb _database_code_depnum_ccdc_archive 'CCDC 695300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 O2' _chemical_formula_weight 366.44 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.0543(5) _cell_length_b 11.0691(4) _cell_length_c 15.2735(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.434(2) _cell_angle_gamma 90.00 _cell_volume 2081.27(13) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 110 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.5 _exptl_crystal_description Rods _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius-Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12036 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.69 _reflns_number_total 1965 _reflns_number_gt 1287 _reflns_threshold_expression >2sigma(I) _computing_data_collection Bruker-Nonius _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (CCDC.cam.ac.uk)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.1864P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1965 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.21598(9) 0.52685(11) 0.01720(8) 0.0728(4) Uani 1 1 d . . . C9 C 0.04955(13) 0.42765(13) -0.04918(10) 0.0558(4) Uani 1 1 d . . . C11 C 0.10958(13) 0.51714(14) 0.01068(10) 0.0566(4) Uani 1 1 d . . . C10 C -0.05980(15) 0.41146(15) -0.05926(11) 0.0599(5) Uani 1 1 d . . . C7 C 0.14697(13) 0.29472(14) -0.14016(11) 0.0593(5) Uani 1 1 d . . . C1 C 0.20806(13) 0.22892(13) -0.18687(10) 0.0541(4) Uani 1 1 d . . . C2 C 0.15753(17) 0.15762(16) -0.26400(12) 0.0680(5) Uani 1 1 d . . . C6 C 0.32013(16) 0.23591(16) -0.15520(13) 0.0679(5) Uani 1 1 d . . . C8 C 0.10119(13) 0.35320(14) -0.09913(10) 0.0594(5) Uani 1 1 d . . . C4 C 0.3307(2) 0.10243(18) -0.27354(15) 0.0847(7) Uani 1 1 d . . . C5 C 0.38103(19) 0.17302(18) -0.19794(15) 0.0807(6) Uani 1 1 d . . . C3 C 0.2203(2) 0.09452(18) -0.30639(14) 0.0819(6) Uani 1 1 d . . . C12 C 0.28680(16) 0.5970(2) 0.09007(14) 0.0756(6) Uani 1 1 d . . . C13 C 0.3999(2) 0.5729(4) 0.0915(2) 0.1056(8) Uani 1 1 d . . . H10 H -0.1029(13) 0.3509(15) -0.0998(11) 0.066(5) Uiso 1 1 d . . . H4 H 0.3771(17) 0.059(2) -0.3012(14) 0.111(7) Uiso 1 1 d . . . H6 H 0.3558(15) 0.2837(17) -0.1029(13) 0.089(6) Uiso 1 1 d . . . H12B H 0.2645(15) 0.682(2) 0.0774(13) 0.093(6) Uiso 1 1 d . . . H13B H 0.451(2) 0.609(2) 0.1463(18) 0.133(9) Uiso 1 1 d . . . H13A H 0.406(2) 0.614(2) 0.0391(16) 0.131(10) Uiso 1 1 d . . . H2 H 0.0798(14) 0.1526(15) -0.2846(11) 0.074(5) Uiso 1 1 d . . . H12A H 0.2756(15) 0.5755(17) 0.1499(13) 0.095(6) Uiso 1 1 d . . . H5 H 0.4609(19) 0.1762(19) -0.1714(15) 0.108(7) Uiso 1 1 d . . . H3 H 0.1816(15) 0.0488(18) -0.3567(14) 0.093(6) Uiso 1 1 d . . . H13C H 0.411(2) 0.492(4) 0.089(2) 0.176(16) 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 O1 0.0627(8) 0.0875(9) 0.0741(8) -0.0202(6) 0.0305(6) -0.0049(6) C9 0.0642(11) 0.0545(9) 0.0548(9) -0.0041(7) 0.0281(8) 0.0053(8) C11 0.0571(11) 0.0599(9) 0.0588(9) -0.0029(8) 0.0270(8) 0.0030(8) C10 0.0659(11) 0.0577(10) 0.0594(10) -0.0096(8) 0.0253(8) -0.0018(9) C7 0.0667(11) 0.0561(9) 0.0611(10) -0.0031(7) 0.0294(9) 0.0026(8) C1 0.0657(11) 0.0483(9) 0.0559(9) 0.0012(7) 0.0303(8) 0.0060(8) C2 0.0788(14) 0.0662(11) 0.0642(10) -0.0054(9) 0.0305(10) -0.0007(10) C6 0.0716(13) 0.0659(11) 0.0710(12) -0.0031(9) 0.0302(10) 0.0071(9) C8 0.0659(11) 0.0580(10) 0.0596(9) -0.0042(8) 0.0278(9) 0.0013(8) C4 0.1106(19) 0.0698(12) 0.0997(16) 0.0008(11) 0.0695(15) 0.0168(12) C5 0.0803(15) 0.0757(13) 0.0990(15) 0.0011(11) 0.0470(13) 0.0147(11) C3 0.120(2) 0.0700(12) 0.0680(12) -0.0146(10) 0.0476(13) -0.0025(12) C12 0.0688(13) 0.0845(15) 0.0718(12) -0.0076(11) 0.0209(10) -0.0076(11) C13 0.0692(16) 0.141(3) 0.104(2) -0.0104(19) 0.0253(14) -0.0157(16) _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 C11 1.3633(18) . ? O1 C12 1.418(2) . ? C9 C10 1.395(2) . ? C9 C11 1.398(2) . ? C9 C8 1.434(2) . ? C11 C10 1.385(2) 5_565 ? C10 C11 1.385(2) 5_565 ? C10 H10 0.958(17) . ? C7 C8 1.1908(19) . ? C7 C1 1.433(2) . ? C1 C6 1.382(2) . ? C1 C2 1.389(2) . ? C2 C3 1.389(3) . ? C2 H2 0.959(17) . ? C6 C5 1.374(2) . ? C6 H6 0.942(19) . ? C4 C3 1.363(3) . ? C4 C5 1.368(3) . ? C4 H4 0.97(2) . ? C5 H5 0.99(2) . ? C3 H3 0.92(2) . ? C12 C13 1.493(3) . ? C12 H12B 0.99(2) . ? C12 H12A 1.001(19) . ? C13 H13B 0.97(3) . ? C13 H13A 0.94(2) . ? C13 H13C 0.91(4) . ? 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 C11 O1 C12 118.87(13) . . ? C10 C9 C11 119.56(13) . . ? C10 C9 C8 120.80(14) . . ? C11 C9 C8 119.63(14) . . ? O1 C11 C10 124.34(15) . 5_565 ? O1 C11 C9 116.07(13) . . ? C10 C11 C9 119.59(15) 5_565 . ? C11 C10 C9 120.85(15) 5_565 . ? C11 C10 H10 117.8(9) 5_565 . ? C9 C10 H10 121.4(9) . . ? C8 C7 C1 176.37(18) . . ? C6 C1 C2 118.53(15) . . ? C6 C1 C7 119.80(15) . . ? C2 C1 C7 121.68(16) . . ? C1 C2 C3 119.6(2) . . ? C1 C2 H2 117.6(10) . . ? C3 C2 H2 122.8(10) . . ? C5 C6 C1 121.18(19) . . ? C5 C6 H6 119.1(11) . . ? C1 C6 H6 119.7(11) . . ? C7 C8 C9 177.51(17) . . ? C3 C4 C5 119.97(19) . . ? C3 C4 H4 123.0(12) . . ? C5 C4 H4 117.1(12) . . ? C4 C5 C6 119.9(2) . . ? C4 C5 H5 120.9(12) . . ? C6 C5 H5 119.1(12) . . ? C4 C3 C2 120.8(2) . . ? C4 C3 H3 124.3(12) . . ? C2 C3 H3 114.9(12) . . ? O1 C12 C13 107.29(19) . . ? O1 C12 H12B 107.3(11) . . ? C13 C12 H12B 113.5(11) . . ? O1 C12 H12A 109.4(11) . . ? C13 C12 H12A 112.8(11) . . ? H12B C12 H12A 106.4(16) . . ? C12 C13 H13B 109.2(15) . . ? C12 C13 H13A 104.9(15) . . ? H13B C13 H13A 108(2) . . ? C12 C13 H13C 110(2) . . ? H13B C13 H13C 112(3) . . ? H13A C13 H13C 112(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.120 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.033 # Attachment 'Propoxy.cif' data_tryf _database_code_depnum_ccdc_archive 'CCDC 695301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 O2' _chemical_formula_weight 394.48 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.78560(10) _cell_length_b 14.9764(4) _cell_length_c 13.3619(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.1120(10) _cell_angle_gamma 90.00 _cell_volume 1157.77(5) _cell_formula_units_Z 2 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 130 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.5 _exptl_crystal_description Bolock _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.132 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius-Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15485 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.69 _reflns_number_total 2191 _reflns_number_gt 1459 _reflns_threshold_expression >2sigma(I) _computing_data_collection Bruker-Nonius _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (CCDC.cam.ac.uk)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.1201P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2191 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C9 C 0.3756(3) 0.45081(9) 0.92963(11) 0.0647(4) Uani 1 1 d . . . O1 O 0.6158(2) 0.49845(7) 0.79980(8) 0.0854(4) Uani 1 1 d . . . C10 C 0.3093(3) 0.45129(10) 1.03016(12) 0.0686(4) Uani 1 1 d . . . C1 C 0.0263(2) 0.31117(9) 0.71804(11) 0.0637(4) Uani 1 1 d . . . C11 C 0.5673(3) 0.50079(9) 0.89965(11) 0.0659(4) Uani 1 1 d . . . C7 C 0.1458(3) 0.35840(10) 0.79561(12) 0.0695(4) Uani 1 1 d . . . C8 C 0.2498(3) 0.39973(10) 0.85739(12) 0.0700(4) Uani 1 1 d . . . C6 C 0.1136(4) 0.30947(12) 0.62217(13) 0.0806(5) Uani 1 1 d . . . C5 C -0.0006(4) 0.26447(13) 0.54675(15) 0.0918(6) Uani 1 1 d . . . C2 C -0.1763(3) 0.26640(14) 0.73682(15) 0.0922(6) Uani 1 1 d . . . C4 C -0.1985(4) 0.22025(14) 0.56594(17) 0.0972(6) Uani 1 1 d . . . C12 C 0.7989(3) 0.55317(13) 0.76162(14) 0.0835(5) Uani 1 1 d . . . C3 C -0.2868(4) 0.22111(17) 0.66019(18) 0.1104(7) Uani 1 1 d . . . C13 C 0.7830(5) 0.54814(18) 0.64894(16) 0.1086(7) Uani 1 1 d . . . C14 C 0.5673(6) 0.5911(3) 0.6083(2) 0.1347(10) Uani 1 1 d . . . H10 H 0.176(3) 0.4193(10) 1.0496(11) 0.074(4) Uiso 1 1 d . . . H12B H 0.774(3) 0.6168(11) 0.7872(11) 0.077(5) Uiso 1 1 d . . . H12A H 0.959(3) 0.5323(13) 0.7859(14) 0.114(6) Uiso 1 1 d . . . H6 H 0.257(3) 0.3386(13) 0.6106(13) 0.098(6) Uiso 1 1 d . . . H2 H -0.246(3) 0.2689(14) 0.8048(17) 0.118(7) Uiso 1 1 d . . . H13B H 0.787(4) 0.4885(19) 0.6191(18) 0.146(9) Uiso 1 1 d . . . H4 H -0.268(4) 0.1873(15) 0.5117(18) 0.130(7) Uiso 1 1 d . . . H5 H 0.065(3) 0.2657(13) 0.4818(17) 0.115(7) Uiso 1 1 d . . . H14C H 0.563(6) 0.667(3) 0.630(3) 0.231(16) Uiso 1 1 d . . . H13A H 0.934(5) 0.5711(17) 0.6205(18) 0.145(9) Uiso 1 1 d . . . H14B H 0.413(5) 0.557(2) 0.642(2) 0.176(11) Uiso 1 1 d . . . H3 H -0.429(5) 0.1902(18) 0.675(2) 0.167(10) Uiso 1 1 d . . . H14A H 0.558(5) 0.584(2) 0.533(3) 0.189(11) 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 C9 0.0799(9) 0.0504(8) 0.0638(9) 0.0043(7) -0.0208(7) -0.0030(7) O1 0.1164(9) 0.0771(8) 0.0627(7) 0.0012(5) -0.0043(6) -0.0200(6) C10 0.0793(10) 0.0578(9) 0.0685(10) 0.0064(7) -0.0136(8) -0.0096(8) C1 0.0719(9) 0.0566(8) 0.0625(9) -0.0020(7) -0.0114(7) -0.0010(7) C11 0.0850(10) 0.0538(8) 0.0590(9) 0.0062(7) -0.0138(7) -0.0011(7) C7 0.0820(10) 0.0596(9) 0.0669(10) 0.0027(7) -0.0128(8) -0.0060(8) C8 0.0849(10) 0.0589(9) 0.0662(10) 0.0041(7) -0.0162(8) -0.0045(8) C6 0.0944(12) 0.0753(11) 0.0719(11) -0.0013(8) 0.0002(9) -0.0152(9) C5 0.1306(17) 0.0823(12) 0.0625(11) -0.0089(9) -0.0042(11) -0.0055(11) C2 0.0837(12) 0.1159(15) 0.0769(12) -0.0151(11) 0.0009(9) -0.0260(10) C4 0.1132(15) 0.0925(14) 0.0858(14) -0.0161(11) -0.0289(12) -0.0128(12) C12 0.0903(12) 0.0756(12) 0.0845(13) 0.0090(10) 0.0063(9) 0.0035(10) C3 0.0874(13) 0.141(2) 0.1032(16) -0.0246(14) -0.0080(11) -0.0396(13) C13 0.136(2) 0.1055(18) 0.0839(14) 0.0047(13) 0.0285(13) 0.0110(15) C14 0.149(2) 0.176(3) 0.0794(16) 0.0220(18) -0.0035(15) 0.005(2) _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 C9 C11 1.397(2) . ? C9 C10 1.398(2) . ? C9 C8 1.430(2) . ? O1 C11 1.3644(18) . ? O1 C12 1.434(2) . ? C10 C11 1.379(2) 3_667 ? C10 H10 0.944(15) . ? C1 C2 1.374(2) . ? C1 C6 1.378(2) . ? C1 C7 1.432(2) . ? C11 C10 1.379(2) 3_667 ? C7 C8 1.194(2) . ? C6 C5 1.380(3) . ? C6 H6 0.951(19) . ? C5 C4 1.348(3) . ? C5 H5 0.95(2) . ? C2 C3 1.384(3) . ? C2 H2 1.00(2) . ? C4 C3 1.360(3) . ? C4 H4 0.96(2) . ? C12 C13 1.510(3) . ? C12 H12B 1.022(16) . ? C12 H12A 1.03(2) . ? C3 H3 0.96(3) . ? C13 C14 1.504(4) . ? C13 H13B 0.98(3) . ? C13 H13A 1.02(3) . ? C14 H14C 1.17(4) . ? C14 H14B 1.12(3) . ? C14 H14A 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 C11 C9 C10 119.50(13) . . ? C11 C9 C8 119.77(14) . . ? C10 C9 C8 120.73(14) . . ? C11 O1 C12 119.13(13) . . ? C11 C10 C9 120.88(15) 3_667 . ? C11 C10 H10 119.9(9) 3_667 . ? C9 C10 H10 119.2(9) . . ? C2 C1 C6 118.37(15) . . ? C2 C1 C7 121.32(15) . . ? C6 C1 C7 120.31(15) . . ? O1 C11 C10 124.82(15) . 3_667 ? O1 C11 C9 115.57(13) . . ? C10 C11 C9 119.61(15) 3_667 . ? C8 C7 C1 177.38(17) . . ? C7 C8 C9 178.63(17) . . ? C1 C6 C5 120.81(19) . . ? C1 C6 H6 117.7(11) . . ? C5 C6 H6 121.5(11) . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5 121.8(13) . . ? C6 C5 H5 117.7(13) . . ? C1 C2 C3 119.82(19) . . ? C1 C2 H2 119.7(12) . . ? C3 C2 H2 120.4(12) . . ? C5 C4 C3 119.50(19) . . ? C5 C4 H4 117.4(14) . . ? C3 C4 H4 123.1(14) . . ? O1 C12 C13 106.40(18) . . ? O1 C12 H12B 108.0(9) . . ? C13 C12 H12B 111.8(9) . . ? O1 C12 H12A 112.3(11) . . ? C13 C12 H12A 110.6(11) . . ? H12B C12 H12A 107.8(14) . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 120.3(16) . . ? C2 C3 H3 118.7(16) . . ? C14 C13 C12 112.8(2) . . ? C14 C13 H13B 105.4(15) . . ? C12 C13 H13B 116.7(14) . . ? C14 C13 H13A 115.8(14) . . ? C12 C13 H13A 107.8(14) . . ? H13B C13 H13A 97.7(19) . . ? C13 C14 H14C 110.3(18) . . ? C13 C14 H14B 108.9(14) . . ? H14C C14 H14B 109(2) . . ? C13 C14 H14A 110.9(18) . . ? H14C C14 H14A 110(2) . . ? H14B C14 H14A 108(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.105 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.025 # Attachment 'Butyloxy.cif' data_try _database_code_depnum_ccdc_archive 'CCDC 695302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 O2' _chemical_formula_weight 422.54 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2637(2) _cell_length_b 21.4804(6) _cell_length_c 9.2590(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.1870(10) _cell_angle_gamma 90.00 _cell_volume 1243.84(6) _cell_formula_units_Z 2 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 95 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25.5 _exptl_crystal_description rod _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius-Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12331 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.65 _reflns_number_total 2323 _reflns_number_gt 1723 _reflns_threshold_expression >2sigma(I) _computing_data_collection Bruker-Nonius _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (CCDC.cam.ac.uk)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.1228P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2323 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.14126(15) 0.05683(4) 0.09992(10) 0.0596(3) Uani 1 1 d . . . C10 C 0.3179(2) 0.02695(6) 0.05520(14) 0.0483(3) Uani 1 1 d . . . C9 C 0.3960(2) 0.04866(6) -0.07478(14) 0.0475(3) Uani 1 1 d . . . C11 C 0.4214(2) -0.02139(6) 0.12787(15) 0.0501(3) Uani 1 1 d . . . C1 C 0.0474(2) 0.18733(6) -0.26663(13) 0.0502(3) Uani 1 1 d . . . C8 C 0.2849(2) 0.09759(6) -0.15201(14) 0.0510(3) Uani 1 1 d . . . C7 C 0.1821(2) 0.13825(6) -0.21033(14) 0.0517(3) Uani 1 1 d . . . C12 C 0.0612(2) 0.03973(7) 0.23632(17) 0.0577(4) Uani 1 1 d . . . C13 C -0.1192(3) 0.08315(8) 0.26666(19) 0.0631(4) Uani 1 1 d . . . C2 C -0.1512(3) 0.19556(8) -0.21263(18) 0.0716(5) Uani 1 1 d . . . C4 C -0.2195(3) 0.28352(8) -0.36460(17) 0.0719(5) Uani 1 1 d . . . C6 C 0.1102(3) 0.22823(8) -0.37160(18) 0.0720(5) Uani 1 1 d . . . C5 C -0.0240(3) 0.27625(8) -0.4182(2) 0.0806(5) Uani 1 1 d . . . C14 C -0.2189(3) 0.06921(11) 0.4080(2) 0.0805(5) Uani 1 1 d . . . C3 C -0.2835(3) 0.24331(9) -0.2613(2) 0.0822(5) Uani 1 1 d . . . C15 C -0.3968(4) 0.11349(15) 0.4399(3) 0.1005(7) Uani 1 1 d . . . H11 H 0.369(2) -0.0373(6) 0.2159(16) 0.059(4) Uiso 1 1 d . . . H12B H 0.178(2) 0.0430(7) 0.3147(17) 0.066(4) Uiso 1 1 d . . . H4 H -0.313(3) 0.3182(9) -0.3979(17) 0.085(5) Uiso 1 1 d . . . H12A H 0.010(2) -0.0050(7) 0.2331(15) 0.065(4) Uiso 1 1 d . . . H13B H -0.225(3) 0.0818(8) 0.186(2) 0.083(5) Uiso 1 1 d . . . H13A H -0.069(3) 0.1260(8) 0.2698(17) 0.077(5) Uiso 1 1 d . . . H2 H -0.200(3) 0.1655(9) -0.143(2) 0.091(5) Uiso 1 1 d . . . H14B H -0.107(3) 0.0707(9) 0.488(2) 0.097(6) Uiso 1 1 d . . . H5 H 0.026(3) 0.3044(9) -0.492(2) 0.106(6) Uiso 1 1 d . . . H15C H -0.507(4) 0.1125(12) 0.353(3) 0.133(9) Uiso 1 1 d . . . H6 H 0.256(3) 0.2239(8) -0.4066(18) 0.088(5) Uiso 1 1 d . . . H14A H -0.271(3) 0.0252(10) 0.406(2) 0.098(6) Uiso 1 1 d . . . H3 H -0.424(3) 0.2477(9) -0.220(2) 0.107(6) Uiso 1 1 d . . . H15B H -0.344(4) 0.1556(15) 0.442(3) 0.161(12) Uiso 1 1 d . . . H15A H -0.469(4) 0.1009(11) 0.523(3) 0.130(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 O1 0.0609(6) 0.0533(6) 0.0656(6) 0.0092(5) 0.0115(5) 0.0133(4) C10 0.0485(7) 0.0397(7) 0.0563(8) -0.0013(6) -0.0005(6) 0.0020(5) C9 0.0523(8) 0.0368(6) 0.0524(8) 0.0009(5) -0.0049(6) 0.0007(6) C11 0.0560(8) 0.0415(7) 0.0527(8) 0.0036(6) 0.0015(6) 0.0013(6) C1 0.0563(8) 0.0462(7) 0.0476(7) 0.0024(6) -0.0003(6) 0.0060(6) C8 0.0558(8) 0.0437(7) 0.0532(8) 0.0003(6) -0.0003(6) 0.0024(6) C7 0.0568(8) 0.0470(7) 0.0513(8) 0.0025(6) 0.0011(6) 0.0045(6) C12 0.0565(9) 0.0547(9) 0.0622(9) 0.0036(7) 0.0051(7) -0.0025(7) C13 0.0602(9) 0.0576(10) 0.0724(10) -0.0012(8) 0.0110(8) -0.0005(7) C2 0.0697(10) 0.0734(11) 0.0731(10) 0.0244(9) 0.0172(8) 0.0160(8) C4 0.0824(12) 0.0687(10) 0.0647(10) 0.0117(8) 0.0052(8) 0.0303(9) C6 0.0662(10) 0.0747(11) 0.0768(10) 0.0247(8) 0.0178(8) 0.0184(8) C5 0.0902(13) 0.0742(11) 0.0791(11) 0.0339(9) 0.0199(9) 0.0242(9) C14 0.0789(12) 0.0917(14) 0.0721(12) 0.0003(10) 0.0144(9) 0.0030(10) C3 0.0700(11) 0.0932(13) 0.0852(12) 0.0221(10) 0.0200(9) 0.0309(10) C15 0.0881(15) 0.123(2) 0.0932(16) -0.0116(14) 0.0315(13) 0.0096(14) _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 C10 1.3630(15) . ? O1 C12 1.4324(17) . ? C10 C11 1.3794(19) . ? C10 C9 1.4040(18) . ? C9 C11 1.3982(18) 3_655 ? C9 C8 1.4302(18) . ? C11 C9 1.3982(18) 3_655 ? C11 H11 0.958(15) . ? C1 C2 1.378(2) . ? C1 C6 1.3834(19) . ? C1 C7 1.4305(18) . ? C8 C7 1.1958(17) . ? C12 C13 1.503(2) . ? C12 H12B 1.006(15) . ? C12 H12A 1.012(15) . ? C13 C14 1.511(2) . ? C13 H13B 0.972(18) . ? C13 H13A 0.973(18) . ? C2 C3 1.378(2) . ? C2 H2 0.972(19) . ? C4 C5 1.356(2) . ? C4 C3 1.365(2) . ? C4 H4 0.987(18) . ? C6 C5 1.385(2) . ? C6 H6 0.988(18) . ? C5 H5 0.98(2) . ? C14 C15 1.507(3) . ? C14 H14B 0.99(2) . ? C14 H14A 1.00(2) . ? C3 H3 0.984(19) . ? C15 H15C 1.03(2) . ? C15 H15B 0.96(3) . ? C15 H15A 0.96(2) . ? 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 C10 O1 C12 118.49(10) . . ? O1 C10 C11 125.01(12) . . ? O1 C10 C9 115.57(11) . . ? C11 C10 C9 119.42(12) . . ? C11 C9 C10 119.56(12) 3_655 . ? C11 C9 C8 121.13(12) 3_655 . ? C10 C9 C8 119.30(12) . . ? C10 C11 C9 121.02(13) . 3_655 ? C10 C11 H11 120.6(8) . . ? C9 C11 H11 118.4(8) 3_655 . ? C2 C1 C6 118.11(13) . . ? C2 C1 C7 119.25(13) . . ? C6 C1 C7 122.62(13) . . ? C7 C8 C9 175.83(14) . . ? C8 C7 C1 174.05(14) . . ? O1 C12 C13 108.02(12) . . ? O1 C12 H12B 109.9(8) . . ? C13 C12 H12B 110.4(8) . . ? O1 C12 H12A 110.0(8) . . ? C13 C12 H12A 110.9(8) . . ? H12B C12 H12A 107.7(12) . . ? C12 C13 C14 112.95(15) . . ? C12 C13 H13B 109.0(10) . . ? C14 C13 H13B 111.3(10) . . ? C12 C13 H13A 110.4(9) . . ? C14 C13 H13A 108.1(9) . . ? H13B C13 H13A 104.8(14) . . ? C1 C2 C3 121.03(15) . . ? C1 C2 H2 118.5(10) . . ? C3 C2 H2 120.3(10) . . ? C5 C4 C3 119.36(15) . . ? C5 C4 H4 120.4(9) . . ? C3 C4 H4 120.3(9) . . ? C1 C6 C5 120.06(15) . . ? C1 C6 H6 118.3(10) . . ? C5 C6 H6 121.5(10) . . ? C4 C5 C6 121.11(16) . . ? C4 C5 H5 121.0(11) . . ? C6 C5 H5 117.9(11) . . ? C15 C14 C13 112.98(19) . . ? C15 C14 H14B 109.5(11) . . ? C13 C14 H14B 109.3(11) . . ? C15 C14 H14A 110.7(11) . . ? C13 C14 H14A 108.9(11) . . ? H14B C14 H14A 105.1(16) . . ? C4 C3 C2 120.33(16) . . ? C4 C3 H3 121.1(11) . . ? C2 C3 H3 118.6(12) . . ? C14 C15 H15C 107.7(13) . . ? C14 C15 H15B 109.8(17) . . ? H15C C15 H15B 105(2) . . ? C14 C15 H15A 111.6(14) . . ? H15C C15 H15A 107.4(19) . . ? H15B C15 H15A 115(2) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.65 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.122 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.025 # Attachment 'Pentyloxy.cif' data_trye _database_code_depnum_ccdc_archive 'CCDC 695303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 O2' _chemical_formula_weight 450.60 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2298(2) _cell_length_b 22.1029(6) _cell_length_c 10.0247(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.168(2) _cell_angle_gamma 90.00 _cell_volume 1362.73(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 96 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25.5 _exptl_crystal_description Rod _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14626 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2586 _reflns_number_gt 1782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius ' _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (CCDC.cam.ac.uk)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1058P)^2^+0.1191P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2586 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6542(2) 0.05627(6) 0.09006(14) 0.0654(5) Uani 1 1 d . . . C10 C 0.8252(3) 0.02654(8) 0.04969(19) 0.0520(5) Uani 1 1 d . . . C9 C 0.8938(3) 0.04955(8) -0.06668(18) 0.0501(5) Uani 1 1 d . . . C11 C 0.9308(3) -0.02290(8) 0.11520(19) 0.0528(5) Uani 1 1 d . . . C8 C 0.7798(3) 0.09981(8) -0.13667(19) 0.0548(5) Uani 1 1 d . . . C1 C 0.5465(3) 0.19002(9) -0.2500(2) 0.0591(5) Uani 1 1 d . . . C6 C 0.3631(4) 0.20608(12) -0.1977(3) 0.0790(7) Uani 1 1 d . . . C13 C 0.4112(4) 0.08160(11) 0.2406(3) 0.0658(6) Uani 1 1 d . . . C12 C 0.5866(4) 0.03817(10) 0.2136(2) 0.0627(6) Uani 1 1 d . . . C7 C 0.6784(3) 0.14069(9) -0.1911(2) 0.0601(5) Uani 1 1 d . . . C2 C 0.5978(4) 0.22266(11) -0.3580(3) 0.0789(7) Uani 1 1 d . . . C3 C 0.4675(5) 0.26980(12) -0.4121(3) 0.0897(8) Uani 1 1 d . . . C14 C 0.3291(4) 0.06831(12) 0.3714(3) 0.0744(7) Uani 1 1 d . . . C5 C 0.2336(5) 0.25366(13) -0.2526(3) 0.0893(8) Uani 1 1 d . . . C4 C 0.2866(4) 0.28521(12) -0.3596(3) 0.0820(8) Uani 1 1 d . . . C15 C 0.1547(6) 0.11160(14) 0.3990(3) 0.0911(9) Uani 1 1 d . . . C16 C 0.0701(8) 0.0981(2) 0.5294(4) 0.1149(12) Uani 1 1 d . . . H14B H 0.445(4) 0.0693(11) 0.458(3) 0.092(8) Uiso 1 1 d . . . H14A H 0.278(4) 0.0233(14) 0.371(3) 0.110(9) Uiso 1 1 d . . . H12B H 0.721(4) 0.0382(10) 0.295(2) 0.083(7) Uiso 1 1 d . . . H11 H 0.898(3) -0.0458(9) 0.208(2) 0.065(6) Uiso 1 1 d . . . H16C H 0.012(5) 0.0601(17) 0.518(3) 0.124(12) Uiso 1 1 d . . . H15B H 0.215(5) 0.1500(16) 0.416(3) 0.124(11) Uiso 1 1 d . . . H13B H 0.471(4) 0.1206(13) 0.247(2) 0.090(8) Uiso 1 1 d . . . H12A H 0.530(3) -0.0060(10) 0.205(2) 0.072(6) Uiso 1 1 d . . . H5 H 0.104(5) 0.2611(13) -0.213(3) 0.114(9) Uiso 1 1 d . . . H6 H 0.319(5) 0.1825(13) -0.134(3) 0.107(9) Uiso 1 1 d . . . H16B H 0.199(8) 0.101(2) 0.616(5) 0.21(2) Uiso 1 1 d . . . H2 H 0.726(5) 0.2113(12) -0.394(3) 0.103(8) Uiso 1 1 d . . . H15A H 0.033(6) 0.1151(16) 0.317(4) 0.139(13) Uiso 1 1 d . . . H16A H -0.033(7) 0.1305(18) 0.565(4) 0.165(14) Uiso 1 1 d . . . H3 H 0.504(5) 0.2918(14) -0.495(3) 0.127(10) Uiso 1 1 d . . . H4 H 0.202(4) 0.3193(11) -0.404(2) 0.080(7) Uiso 1 1 d . . . H13A H 0.296(4) 0.0816(11) 0.161(3) 0.090(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 O1 0.0670(9) 0.0628(9) 0.0717(10) 0.0088(6) 0.0268(7) 0.0152(6) C10 0.0501(10) 0.0495(10) 0.0576(11) -0.0059(8) 0.0121(8) 0.0027(8) C9 0.0545(10) 0.0445(10) 0.0504(11) 0.0002(7) 0.0054(8) 0.0032(8) C11 0.0575(11) 0.0506(10) 0.0512(11) 0.0024(8) 0.0118(8) 0.0011(8) C8 0.0593(11) 0.0500(11) 0.0560(11) -0.0021(8) 0.0120(8) 0.0035(9) C1 0.0648(12) 0.0523(11) 0.0586(12) 0.0004(9) 0.0048(9) 0.0084(9) C6 0.0816(16) 0.0789(16) 0.0808(16) 0.0220(13) 0.0263(13) 0.0192(12) C13 0.0675(14) 0.0608(13) 0.0746(15) -0.0008(11) 0.0278(12) 0.0008(11) C12 0.0627(13) 0.0632(13) 0.0657(13) -0.0004(10) 0.0209(10) 0.0006(10) C7 0.0662(12) 0.0541(11) 0.0596(12) 0.0001(9) 0.0091(9) 0.0059(10) C2 0.0846(16) 0.0781(15) 0.0784(16) 0.0166(12) 0.0262(13) 0.0261(13) C3 0.112(2) 0.0827(16) 0.0794(17) 0.0275(13) 0.0308(15) 0.0326(15) C14 0.0743(15) 0.0782(16) 0.0746(16) -0.0024(12) 0.0238(12) 0.0012(12) C5 0.0851(17) 0.0941(18) 0.0937(19) 0.0151(14) 0.0290(14) 0.0362(14) C4 0.0974(18) 0.0738(15) 0.0740(16) 0.0125(12) 0.0115(13) 0.0338(13) C15 0.096(2) 0.0861(19) 0.101(2) -0.0121(16) 0.0455(18) 0.0050(16) C16 0.136(3) 0.119(3) 0.105(3) -0.025(2) 0.068(2) -0.013(2) _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 C10 1.366(2) . ? O1 C12 1.428(2) . ? C10 C11 1.386(3) . ? C10 C9 1.400(3) . ? C9 C11 1.396(3) 3_755 ? C9 C8 1.439(3) . ? C11 C9 1.396(2) 3_755 ? C11 H11 1.10(2) . ? C8 C7 1.185(3) . ? C1 C6 1.377(3) . ? C1 C2 1.381(3) . ? C1 C7 1.434(3) . ? C6 C5 1.385(3) . ? C6 H6 0.90(3) . ? C13 C12 1.511(3) . ? C13 C14 1.511(3) . ? C13 H13B 0.94(3) . ? C13 H13A 0.98(3) . ? C12 H12B 1.07(2) . ? C12 H12A 1.04(2) . ? C2 C3 1.378(3) . ? C2 H2 0.96(3) . ? C3 C4 1.361(4) . ? C3 H3 1.02(3) . ? C14 C15 1.506(4) . ? C14 H14B 1.04(3) . ? C14 H14A 1.05(3) . ? C5 C4 1.363(4) . ? C5 H5 0.97(3) . ? C4 H4 0.98(2) . ? C15 C16 1.515(4) . ? C15 H15B 0.93(3) . ? C15 H15A 1.03(4) . ? C16 H16C 0.91(4) . ? C16 H16B 1.09(5) . ? C16 H16A 1.06(4) . ? 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 C10 O1 C12 118.29(15) . . ? O1 C10 C11 124.92(17) . . ? O1 C10 C9 115.33(16) . . ? C11 C10 C9 119.75(16) . . ? C11 C9 C10 119.81(16) 3_755 . ? C11 C9 C8 120.57(16) 3_755 . ? C10 C9 C8 119.61(16) . . ? C10 C11 C9 120.44(17) . 3_755 ? C10 C11 H11 128.4(10) . . ? C9 C11 H11 111.2(10) 3_755 . ? C7 C8 C9 177.0(2) . . ? C6 C1 C2 118.3(2) . . ? C6 C1 C7 119.7(2) . . ? C2 C1 C7 122.07(19) . . ? C1 C6 C5 120.7(2) . . ? C1 C6 H6 119.0(19) . . ? C5 C6 H6 119.9(19) . . ? C12 C13 C14 112.7(2) . . ? C12 C13 H13B 107.7(15) . . ? C14 C13 H13B 108.0(14) . . ? C12 C13 H13A 108.1(14) . . ? C14 C13 H13A 113.4(14) . . ? H13B C13 H13A 107(2) . . ? O1 C12 C13 107.40(17) . . ? O1 C12 H12B 110.9(12) . . ? C13 C12 H12B 111.3(12) . . ? O1 C12 H12A 109.7(12) . . ? C13 C12 H12A 111.6(12) . . ? H12B C12 H12A 106.0(16) . . ? C8 C7 C1 176.1(2) . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2 121.5(16) . . ? C1 C2 H2 117.9(16) . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 120.1(18) . . ? C2 C3 H3 119.3(18) . . ? C15 C14 C13 112.9(2) . . ? C15 C14 H14B 104.9(14) . . ? C13 C14 H14B 116.0(14) . . ? C15 C14 H14A 112.1(15) . . ? C13 C14 H14A 109.3(14) . . ? H14B C14 H14A 101(2) . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 123.8(17) . . ? C6 C5 H5 116.0(17) . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4 115.7(13) . . ? C5 C4 H4 124.6(13) . . ? C14 C15 C16 113.2(3) . . ? C14 C15 H15B 109(2) . . ? C16 C15 H15B 102(2) . . ? C14 C15 H15A 111(2) . . ? C16 C15 H15A 113(2) . . ? H15B C15 H15A 107(3) . . ? C15 C16 H16C 105(2) . . ? C15 C16 H16B 111(3) . . ? H16C C16 H16B 113(4) . . ? C15 C16 H16A 118(2) . . ? H16C C16 H16A 114(3) . . ? H16B C16 H16A 96(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.090 # Attachment 'Hexyloxy.cif' data_tryc _database_code_depnum_ccdc_archive 'CCDC 695304' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H38 O2' _chemical_formula_weight 478.64 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2970(2) _cell_length_b 22.7824(8) _cell_length_c 10.6411(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.4930(10) _cell_angle_gamma 90.00 _cell_volume 1471.11(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 85 _cell_measurement_theta_min 2 _cell_measurement_theta_max 23 _exptl_crystal_description Rod _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.081 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5968 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 23.24 _reflns_number_total 2087 _reflns_number_gt 1522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius ' _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (ccdc.cam.ac.uk)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2087 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.82741(19) 0.05354(5) 0.91217(11) 0.0581(4) Uani 1 1 d . . . C10 C 0.6654(3) 0.02559(7) 0.95217(15) 0.0476(4) Uani 1 1 d . . . C9 C 0.6090(3) 0.05007(6) 1.05944(14) 0.0475(4) Uani 1 1 d . . . C11 C 0.5551(3) -0.02436(7) 0.89386(17) 0.0506(5) Uani 1 1 d . . . C12 C 0.8814(3) 0.03282(8) 0.79764(17) 0.0543(5) Uani 1 1 d . . . C14 C 1.1108(3) 0.05700(8) 0.64490(19) 0.0618(5) Uani 1 1 d . . . C13 C 1.0476(3) 0.07358(8) 0.76770(18) 0.0578(5) Uani 1 1 d . . . C7 C 0.8267(3) 0.14280(7) 1.17297(16) 0.0574(5) Uani 1 1 d . . . C8 C 0.7258(3) 0.10097(7) 1.12224(15) 0.0526(5) Uani 1 1 d . . . C1 C 0.9522(3) 0.19346(7) 1.23079(17) 0.0594(5) Uani 1 1 d . . . C6 C 1.1239(4) 0.21323(9) 1.1846(2) 0.0780(6) Uani 1 1 d . . . C16 C 1.3327(4) 0.08437(11) 0.4861(2) 0.0764(6) Uani 1 1 d . . . C2 C 0.9036(4) 0.22302(9) 1.3328(2) 0.0824(7) Uani 1 1 d . . . C15 C 1.2707(4) 0.09945(9) 0.6094(2) 0.0664(5) Uani 1 1 d . . . C3 C 1.0266(5) 0.27156(10) 1.3882(3) 0.0970(8) Uani 1 1 d . . . C5 C 1.2450(4) 0.26230(10) 1.2410(3) 0.0915(7) Uani 1 1 d . . . C4 C 1.1947(5) 0.29075(10) 1.3421(2) 0.0908(8) Uani 1 1 d . . . C17 C 1.5003(5) 0.12527(14) 0.4558(3) 0.0937(8) Uani 1 1 d . . . H12B H 0.941(3) -0.0076(8) 0.8113(14) 0.056(4) Uiso 1 1 d . . . H6 H 1.162(3) 0.1928(9) 1.1142(19) 0.090(7) Uiso 1 1 d . . . H14B H 1.180(3) 0.0163(8) 0.6545(16) 0.072(5) Uiso 1 1 d . . . H11 H 0.593(3) -0.0409(7) 0.8241(16) 0.053(5) Uiso 1 1 d . . . H12A H 0.739(3) 0.0314(7) 0.7246(17) 0.062(5) Uiso 1 1 d . . . H15B H 1.210(3) 0.1392(9) 0.5977(17) 0.082(6) Uiso 1 1 d . . . H13B H 1.182(3) 0.0749(8) 0.8444(18) 0.072(5) Uiso 1 1 d . . . H14A H 0.978(3) 0.0536(7) 0.5712(18) 0.072(6) Uiso 1 1 d . . . H13A H 0.986(3) 0.1124(8) 0.7560(15) 0.063(5) Uiso 1 1 d . . . H15A H 1.403(4) 0.1012(9) 0.681(2) 0.091(7) Uiso 1 1 d . . . H16B H 1.193(4) 0.0842(10) 0.415(2) 0.103(8) Uiso 1 1 d . . . H5 H 1.367(4) 0.2731(10) 1.206(2) 0.106(8) Uiso 1 1 d . . . H16A H 1.387(3) 0.0433(10) 0.4954(19) 0.096(7) Uiso 1 1 d . . . H17C H 1.643(5) 0.1282(13) 0.529(3) 0.149(11) Uiso 1 1 d . . . H17B H 1.430(4) 0.1660(14) 0.451(2) 0.139(11) Uiso 1 1 d . . . H2 H 0.782(4) 0.2119(10) 1.368(2) 0.107(8) Uiso 1 1 d . . . H17A H 1.543(4) 0.1146(12) 0.376(3) 0.132(9) Uiso 1 1 d . . . H4 H 1.284(3) 0.3255(10) 1.3827(18) 0.093(6) Uiso 1 1 d . . . H3 H 0.991(4) 0.2917(11) 1.466(3) 0.137(9) 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 O1 0.0625(8) 0.0547(7) 0.0613(7) -0.0086(5) 0.0242(6) -0.0126(6) C10 0.0480(10) 0.0449(9) 0.0489(10) 0.0009(7) 0.0112(8) -0.0022(7) C9 0.0500(10) 0.0424(9) 0.0470(9) -0.0020(7) 0.0073(8) -0.0010(7) C11 0.0564(11) 0.0477(9) 0.0475(10) -0.0052(8) 0.0132(8) -0.0019(8) C12 0.0552(11) 0.0537(11) 0.0552(11) -0.0025(8) 0.0170(9) 0.0024(9) C14 0.0646(13) 0.0615(12) 0.0609(12) 0.0008(9) 0.0194(10) 0.0025(10) C13 0.0611(12) 0.0536(11) 0.0611(12) 0.0009(9) 0.0208(10) 0.0012(9) C7 0.0645(12) 0.0506(10) 0.0542(11) -0.0031(8) 0.0108(8) -0.0071(9) C8 0.0577(11) 0.0492(10) 0.0504(10) -0.0016(8) 0.0132(8) -0.0034(8) C1 0.0676(12) 0.0484(9) 0.0562(11) 0.0006(8) 0.0061(9) -0.0115(9) C6 0.0876(16) 0.0723(13) 0.0744(14) -0.0089(11) 0.0221(12) -0.0240(12) C16 0.0855(16) 0.0799(15) 0.0717(14) 0.0025(11) 0.0345(13) -0.0015(13) C2 0.0980(17) 0.0700(13) 0.0835(15) -0.0222(11) 0.0316(13) -0.0266(12) C15 0.0697(14) 0.0663(13) 0.0680(14) 0.0022(10) 0.0268(11) 0.0013(10) C3 0.126(2) 0.0764(15) 0.0889(17) -0.0278(13) 0.0297(15) -0.0334(15) C5 0.0974(18) 0.0839(15) 0.0921(17) 0.0034(13) 0.0231(14) -0.0382(14) C4 0.114(2) 0.0662(13) 0.0801(16) -0.0058(12) 0.0055(14) -0.0347(13) C17 0.097(2) 0.112(2) 0.0838(18) 0.0039(15) 0.0447(16) -0.0087(16) _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 C10 1.3633(18) . ? O1 C12 1.4301(19) . ? C10 C11 1.390(2) . ? C10 C9 1.399(2) . ? C9 C11 1.390(2) 3_657 ? C9 C8 1.439(2) . ? C11 C9 1.390(2) 3_657 ? C11 H11 0.919(16) . ? C12 C13 1.496(2) . ? C12 H12B 0.991(17) . ? C12 H12A 1.016(17) . ? C14 C13 1.512(2) . ? C14 C15 1.515(3) . ? C14 H14B 1.017(19) . ? C14 H14A 0.986(19) . ? C13 H13B 1.007(18) . ? C13 H13A 0.961(18) . ? C7 C8 1.191(2) . ? C7 C1 1.441(2) . ? C1 C6 1.377(3) . ? C1 C2 1.380(3) . ? C6 C5 1.395(3) . ? C6 H6 0.96(2) . ? C16 C15 1.505(3) . ? C16 C17 1.506(3) . ? C16 H16B 0.99(2) . ? C16 H16A 0.99(2) . ? C2 C3 1.388(3) . ? C2 H2 0.97(2) . ? C15 H15B 0.98(2) . ? C15 H15A 0.97(2) . ? C3 C4 1.353(3) . ? C3 H3 1.02(3) . ? C5 C4 1.363(3) . ? C5 H5 0.97(2) . ? C4 H4 1.00(2) . ? C17 H17C 1.02(3) . ? C17 H17B 1.02(3) . ? C17 H17A 0.99(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 C10 O1 C12 118.68(12) . . ? O1 C10 C11 124.70(15) . . ? O1 C10 C9 116.29(13) . . ? C11 C10 C9 119.02(15) . . ? C11 C9 C10 119.93(14) 3_657 . ? C11 C9 C8 120.68(14) 3_657 . ? C10 C9 C8 119.38(14) . . ? C10 C11 C9 121.06(16) . 3_657 ? C10 C11 H11 119.2(10) . . ? C9 C11 H11 119.7(10) 3_657 . ? O1 C12 C13 108.41(14) . . ? O1 C12 H12B 110.5(9) . . ? C13 C12 H12B 110.3(9) . . ? O1 C12 H12A 107.5(9) . . ? C13 C12 H12A 112.3(9) . . ? H12B C12 H12A 107.8(12) . . ? C13 C14 C15 113.68(16) . . ? C13 C14 H14B 110.2(10) . . ? C15 C14 H14B 108.1(10) . . ? C13 C14 H14A 110.0(10) . . ? C15 C14 H14A 109.4(10) . . ? H14B C14 H14A 105.0(14) . . ? C12 C13 C14 112.92(15) . . ? C12 C13 H13B 109.2(10) . . ? C14 C13 H13B 110.5(10) . . ? C12 C13 H13A 108.4(10) . . ? C14 C13 H13A 108.0(10) . . ? H13B C13 H13A 107.5(14) . . ? C8 C7 C1 178.07(19) . . ? C7 C8 C9 178.39(19) . . ? C6 C1 C2 118.78(18) . . ? C6 C1 C7 120.20(17) . . ? C2 C1 C7 121.02(17) . . ? C1 C6 C5 120.0(2) . . ? C1 C6 H6 120.0(13) . . ? C5 C6 H6 120.1(13) . . ? C15 C16 C17 113.9(2) . . ? C15 C16 H16B 106.4(12) . . ? C17 C16 H16B 111.5(13) . . ? C15 C16 H16A 106.9(12) . . ? C17 C16 H16A 111.3(13) . . ? H16B C16 H16A 106.4(18) . . ? C1 C2 C3 120.5(2) . . ? C1 C2 H2 122.7(14) . . ? C3 C2 H2 116.8(14) . . ? C16 C15 C14 114.57(18) . . ? C16 C15 H15B 106.5(11) . . ? C14 C15 H15B 111.1(11) . . ? C16 C15 H15A 109.1(12) . . ? C14 C15 H15A 108.6(12) . . ? H15B C15 H15A 106.6(17) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 120.7(15) . . ? C2 C3 H3 119.0(15) . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 124.0(14) . . ? C6 C5 H5 115.7(14) . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 120.4(11) . . ? C5 C4 H4 119.5(12) . . ? C16 C17 H17C 113.7(16) . . ? C16 C17 H17B 104.6(15) . . ? H17C C17 H17B 105(2) . . ? C16 C17 H17A 113.5(16) . . ? H17C C17 H17A 107(2) . . ? H17B C17 H17A 113(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.167 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.035