Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_year 2004 _publ_contact_author 'Todd Marder' _publ_contact_author_email todd.marder@durham.ac.uk _journal_volume ? _journal_page_first ? _journal_page_last ? _publ_section_title ; Synthesis, optical properties, crystal structures and phase behaviour of symmetric, conjugated ethynylarene-based rigid rods with terminal carboxylate groups ; _publ_contact_author_name 'Todd Marder' loop_ _publ_author_name T.M.Fasina J.C.Collings J.M.Burke A.S.Batsanov R.M.Ward ; D.Albesa-Jove ; L.Porres A.Beeby J.A.K.Howard A.J.Scott W.Clegg S.W.Watt ; C.Viney ; T.B.Marder #====================================================================== data_(2) _database_code_depnum_ccdc_archive 'CCDC 249324' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(4'-carbomethoxyphenyl)ethyne ; _chemical_melting_point 491--493 _chemical_name_common 1,2-bis(4'-carbomethoxyphenyl)ethyne _chemical_formula_moiety 'C18 H14 O4' _chemical_formula_sum 'C18 H14 O4' _chemical_formula_weight 294.29 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.1061(8) _cell_length_b 5.9558(7) _cell_length_c 34.129(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1444.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 4860 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 28.25 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 8196 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1667 _reflns_number_gt 1365 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.4261P] 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 SHELXL _refine_ls_extinction_coef 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1667 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4474(2) 0.7175(3) 0.28807(4) 0.0336(4) Uani 1 d . . . H11 H 0.5771 0.7085 0.2784 0.050 Uiso 1 calc R . . H12 H 0.4089 0.8752 0.2896 0.050 Uiso 1 calc R . . H13 H 0.3637 0.6369 0.2701 0.050 Uiso 1 calc R . . O1 O 0.43642(14) 0.61645(16) 0.32679(3) 0.0286(3) Uani 1 d . . . C2 C 0.49915(17) 0.4054(2) 0.32922(4) 0.0227(3) Uani 1 d . . . O2 O 0.55594(16) 0.3000(2) 0.30145(3) 0.0372(3) Uani 1 d . . . C3 C 0.49505(16) 0.3163(2) 0.37000(3) 0.0195(3) Uani 1 d . . . C4 C 0.42423(16) 0.4411(2) 0.40129(4) 0.0203(3) Uani 1 d . . . H4 H 0.3729 0.5861 0.3968 0.024 Uiso 1 calc R . . C5 C 0.42889(17) 0.3530(2) 0.43894(4) 0.0215(3) Uani 1 d . . . H5 H 0.3810 0.4382 0.4603 0.026 Uiso 1 calc R . . C6 C 0.50419(16) 0.1385(2) 0.44559(4) 0.0209(3) Uani 1 d . . . C7 C 0.57586(17) 0.0154(2) 0.41410(4) 0.0225(3) Uani 1 d . . . H7 H 0.6286 -0.1290 0.4185 0.027 Uiso 1 calc R . . C8 C 0.57027(17) 0.1029(2) 0.37664(4) 0.0222(3) Uani 1 d . . . H8 H 0.6178 0.0176 0.3553 0.027 Uiso 1 calc R . . C9 C 0.50313(17) 0.0429(2) 0.48412(4) 0.0238(3) Uani 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 0.0401(8) 0.0355(8) 0.0253(7) 0.0115(6) 0.0015(6) 0.0022(6) O1 0.0380(6) 0.0262(5) 0.0216(5) 0.0056(4) 0.0025(4) 0.0057(4) C2 0.0219(6) 0.0252(6) 0.0212(6) -0.0005(5) -0.0005(5) -0.0008(5) O2 0.0548(7) 0.0353(6) 0.0215(5) -0.0012(4) 0.0058(4) 0.0082(5) C3 0.0170(6) 0.0216(6) 0.0198(6) 0.0010(5) -0.0006(5) -0.0016(5) C4 0.0192(6) 0.0188(6) 0.0230(6) 0.0007(4) -0.0008(5) 0.0013(4) C5 0.0198(6) 0.0240(6) 0.0208(6) -0.0004(5) 0.0011(5) 0.0010(5) C6 0.0162(6) 0.0240(6) 0.0225(6) 0.0041(5) -0.0023(5) -0.0034(5) C7 0.0200(6) 0.0188(6) 0.0287(7) 0.0017(5) -0.0030(5) 0.0010(4) C8 0.0201(6) 0.0221(6) 0.0245(6) -0.0029(5) 0.0002(5) 0.0008(5) C9 0.0197(6) 0.0255(7) 0.0261(6) 0.0031(5) -0.0024(5) -0.0010(5) _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 O1 1.4540(16) . ? O1 C2 1.3362(16) . ? C2 O2 1.2065(16) . ? C2 C3 1.4897(17) . ? C3 C4 1.3950(17) . ? C3 C8 1.3975(17) . ? C4 C5 1.3881(17) . ? C5 C6 1.4035(17) . ? C6 C7 1.3974(18) . ? C6 C9 1.4329(17) . ? C7 C8 1.3813(18) . ? C9 C9 1.199(3) 5_656 ? 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 O1 C1 115.33(10) . . ? O2 C2 O1 123.54(12) . . ? O2 C2 C3 123.72(12) . . ? O1 C2 C3 112.73(11) . . ? C4 C3 C8 119.89(11) . . ? C4 C3 C2 122.19(11) . . ? C8 C3 C2 117.90(11) . . ? C5 C4 C3 119.92(11) . . ? C4 C5 C6 120.19(11) . . ? C7 C6 C5 119.49(11) . . ? C7 C6 C9 119.94(11) . . ? C5 C6 C9 120.55(11) . . ? C8 C7 C6 120.23(11) . . ? C7 C8 C3 120.28(11) . . ? C9 C9 C6 177.41(18) 5_656 . ? _diffrn_measured_fraction_theta_max 0.786 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.833 _refine_diff_density_max 0.362 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.039 #================================================END data_(6) _database_code_depnum_ccdc_archive 'CCDC 249325' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Bis(4-carbomethoxyphenyl)butadiyne ; _chemical_name_common 1,4-Bis(4-carbomethoxyphenyl)butadiyne _chemical_melting_point 463--464 _chemical_formula_moiety 'C20 H14 O4' _chemical_formula_sum 'C20 H14 O4' _chemical_formula_weight 318.31 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0249(5) _cell_length_b 10.4613(8) _cell_length_c 11.7016(8) _cell_angle_alpha 75.204(3) _cell_angle_beta 72.585(3) _cell_angle_gamma 75.457(3) _cell_volume 779.0(1) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 884 _cell_measurement_theta_min 6.190 _cell_measurement_theta_max 60.873 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ;The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 3 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.95 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '60W microfocus Bede Microsource with glass polycapillary optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ProteumM APEX CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 6778 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.50 _reflns_number_total 4305 _reflns_number_gt 3456 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT V6.02a (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Bruker, 2001)' _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. ; _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^)+(0.0663P)^2^+0.1963P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4305 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1307 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.46831(14) 0.16169(10) -0.17472(9) 0.0205(2) Uani 1 1 d . . . O2 O 1.59167(16) 0.14033(11) -0.01323(10) 0.0256(3) Uani 1 1 d . . . O3 O -0.60045(15) 0.89651(11) 0.69760(9) 0.0210(2) Uani 1 1 d . . . O4 O -0.77697(16) 0.85373(12) 0.58505(10) 0.0287(3) Uani 1 1 d . . . C1 C 1.6633(2) 0.09023(16) -0.23387(14) 0.0227(3) Uani 1 1 d . . . H11 H 1.685(3) -0.0015(19) -0.1888(16) 0.025(5) Uiso 1 1 d . . . H12 H 1.652(3) 0.091(2) -0.3183(19) 0.039(5) Uiso 1 1 d . . . H13 H 1.768(3) 0.1394(19) -0.2385(17) 0.031(5) Uiso 1 1 d . . . C2 C 1.4530(2) 0.17758(14) -0.06238(12) 0.0175(3) Uani 1 1 d . . . C3 C 1.2460(2) 0.24665(13) -0.00447(12) 0.0167(3) Uani 1 1 d . . . C4 C 1.0819(2) 0.26805(14) -0.05525(13) 0.0187(3) Uani 1 1 d . . . H4 H 1.099(3) 0.2384(17) -0.1307(16) 0.023(4) Uiso 1 1 d . . . C5 C 0.8913(2) 0.33098(15) 0.00194(13) 0.0192(3) Uani 1 1 d . . . H5 H 0.778(3) 0.3442(18) -0.0341(16) 0.025(4) Uiso 1 1 d . . . C6 C 0.8630(2) 0.37307(13) 0.11105(12) 0.0178(3) Uani 1 1 d . . . C7 C 1.0287(2) 0.35155(14) 0.16184(13) 0.0202(3) Uani 1 1 d . . . H7 H 1.010(3) 0.3798(18) 0.2385(17) 0.027(5) Uiso 1 1 d . . . C8 C 1.2183(2) 0.28865(14) 0.10439(13) 0.0191(3) Uani 1 1 d . . . H8 H 1.329(3) 0.2746(19) 0.1405(17) 0.032(5) Uiso 1 1 d . . . C9 C 0.6653(2) 0.43632(14) 0.17086(13) 0.0199(3) Uani 1 1 d . . . C10 C 0.4975(2) 0.48759(14) 0.22121(13) 0.0200(3) Uani 1 1 d . . . C11 C 0.3076(2) 0.54473(14) 0.28099(12) 0.0195(3) Uani 1 1 d . . . C12 C 0.1416(2) 0.59329(14) 0.33574(13) 0.0189(3) Uani 1 1 d . . . C13 C -0.0498(2) 0.65413(14) 0.40514(12) 0.0172(3) Uani 1 1 d . . . C14 C -0.2336(2) 0.63591(14) 0.39376(13) 0.0188(3) Uani 1 1 d . . . H14 H -0.232(3) 0.5804(19) 0.3386(17) 0.029(5) Uiso 1 1 d . . . C15 C -0.4161(2) 0.69796(15) 0.46109(13) 0.0189(3) Uani 1 1 d . . . H15 H -0.538(3) 0.6836(16) 0.4533(15) 0.019(4) Uiso 1 1 d . . . C16 C -0.4176(2) 0.77831(14) 0.54013(12) 0.0166(3) Uani 1 1 d . . . C17 C -0.2348(2) 0.79545(15) 0.55218(12) 0.0182(3) Uani 1 1 d . . . H17 H -0.235(3) 0.8502(17) 0.6032(16) 0.021(4) Uiso 1 1 d . . . C18 C -0.0519(2) 0.73409(15) 0.48515(12) 0.0187(3) Uani 1 1 d . . . H18 H 0.076(3) 0.7508(16) 0.4906(15) 0.018(4) Uiso 1 1 d . . . C19 C -0.6178(2) 0.84568(14) 0.60818(12) 0.0171(3) Uani 1 1 d . . . C20 C -0.7878(2) 0.96755(16) 0.76567(14) 0.0213(3) Uani 1 1 d . . . H201 H -0.824(3) 1.0544(19) 0.7157(17) 0.026(5) Uiso 1 1 d . . . H202 H -0.754(3) 0.9762(18) 0.8376(17) 0.027(5) Uiso 1 1 d . . . H203 H -0.892(3) 0.914(2) 0.7886(17) 0.033(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 O1 0.0156(5) 0.0242(5) 0.0184(5) -0.0077(4) -0.0008(4) 0.0014(4) O2 0.0174(5) 0.0332(6) 0.0264(6) -0.0098(5) -0.0068(4) 0.0006(4) O3 0.0155(5) 0.0267(5) 0.0220(5) -0.0125(4) -0.0038(4) 0.0010(4) O4 0.0159(5) 0.0413(7) 0.0339(6) -0.0195(5) -0.0078(4) 0.0001(5) C1 0.0172(7) 0.0213(7) 0.0237(7) -0.0068(6) 0.0002(5) 0.0028(6) C2 0.0166(6) 0.0174(6) 0.0180(6) -0.0034(5) -0.0022(5) -0.0048(5) C3 0.0149(6) 0.0156(6) 0.0168(6) -0.0027(5) -0.0012(5) -0.0017(5) C4 0.0182(6) 0.0211(7) 0.0162(6) -0.0052(5) -0.0026(5) -0.0034(5) C5 0.0157(6) 0.0214(7) 0.0193(6) -0.0045(5) -0.0032(5) -0.0023(5) C6 0.0173(6) 0.0146(6) 0.0180(6) -0.0032(5) 0.0005(5) -0.0028(5) C7 0.0228(7) 0.0199(7) 0.0177(6) -0.0063(5) -0.0023(5) -0.0040(5) C8 0.0176(6) 0.0206(7) 0.0197(6) -0.0053(5) -0.0053(5) -0.0026(5) C9 0.0205(7) 0.0195(7) 0.0189(6) -0.0039(5) -0.0027(5) -0.0048(5) C10 0.0202(7) 0.0199(7) 0.0184(6) -0.0030(5) -0.0025(5) -0.0048(5) C11 0.0204(7) 0.0197(7) 0.0172(6) -0.0034(5) -0.0035(5) -0.0034(5) C12 0.0182(6) 0.0209(7) 0.0173(6) -0.0034(5) -0.0043(5) -0.0035(5) C13 0.0169(6) 0.0179(6) 0.0138(6) -0.0023(5) -0.0022(5) -0.0008(5) C14 0.0196(7) 0.0201(7) 0.0175(6) -0.0067(5) -0.0043(5) -0.0026(5) C15 0.0153(6) 0.0231(7) 0.0194(6) -0.0061(5) -0.0054(5) -0.0027(5) C16 0.0147(6) 0.0181(6) 0.0152(6) -0.0030(5) -0.0029(5) -0.0015(5) C17 0.0179(6) 0.0204(7) 0.0170(6) -0.0064(5) -0.0038(5) -0.0028(5) C18 0.0144(6) 0.0228(7) 0.0192(6) -0.0046(5) -0.0039(5) -0.0041(5) C19 0.0160(6) 0.0182(6) 0.0172(6) -0.0041(5) -0.0038(5) -0.0029(5) C20 0.0164(6) 0.0227(7) 0.0224(7) -0.0097(6) -0.0009(5) 0.0013(5) _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 C2 1.3362(17) . ? O1 C1 1.4479(16) . ? O2 C2 1.2090(17) . ? O3 C19 1.3363(17) . ? O3 C20 1.4500(16) . ? O4 C19 1.2053(17) . ? C1 H11 0.968(18) . ? C1 H12 1.01(2) . ? C1 H13 0.98(2) . ? C2 C3 1.4931(18) . ? C3 C4 1.394(2) . ? C3 C8 1.3958(19) . ? C4 C5 1.3855(18) . ? C4 H4 0.974(17) . ? C5 C6 1.398(2) . ? C5 H5 0.971(19) . ? C6 C7 1.405(2) . ? C6 C9 1.4317(18) . ? C7 C8 1.3816(19) . ? C7 H7 0.977(18) . ? C8 H8 0.95(2) . ? C9 C10 1.2054(19) . ? C10 C11 1.3715(19) . ? C11 C12 1.2041(19) . ? C12 C13 1.4325(18) . ? C13 C14 1.400(2) . ? C13 C18 1.401(2) . ? C14 C15 1.3874(18) . ? C14 H14 0.968(19) . ? C15 C16 1.3961(19) . ? C15 H15 0.937(17) . ? C16 C17 1.392(2) . ? C16 C19 1.4925(17) . ? C17 C18 1.3848(18) . ? C17 H17 0.927(18) . ? C18 H18 0.983(18) . ? C20 H201 0.967(18) . ? C20 H202 0.970(19) . ? C20 H203 0.97(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 C2 O1 C1 115.18(11) . . ? C19 O3 C20 115.66(11) . . ? O1 C1 H11 109.0(10) . . ? O1 C1 H12 105.3(11) . . ? H11 C1 H12 109.9(15) . . ? O1 C1 H13 108.2(11) . . ? H11 C1 H13 113.1(15) . . ? H12 C1 H13 111.1(16) . . ? O2 C2 O1 123.69(12) . . ? O2 C2 C3 123.78(13) . . ? O1 C2 C3 112.52(12) . . ? C4 C3 C8 119.95(12) . . ? C4 C3 C2 121.86(12) . . ? C8 C3 C2 118.18(12) . . ? C5 C4 C3 120.23(13) . . ? C5 C4 H4 119.0(10) . . ? C3 C4 H4 120.8(10) . . ? C4 C5 C6 119.97(13) . . ? C4 C5 H5 119.2(10) . . ? C6 C5 H5 120.8(10) . . ? C5 C6 C7 119.64(12) . . ? C5 C6 C9 119.85(13) . . ? C7 C6 C9 120.50(13) . . ? C8 C7 C6 120.08(13) . . ? C8 C7 H7 119.8(10) . . ? C6 C7 H7 120.1(10) . . ? C7 C8 C3 120.11(13) . . ? C7 C8 H8 118.8(11) . . ? C3 C8 H8 121.1(11) . . ? C10 C9 C6 178.81(16) . . ? C9 C10 C11 178.71(16) . . ? C12 C11 C10 178.63(16) . . ? C11 C12 C13 176.38(16) . . ? C14 C13 C18 119.66(12) . . ? C14 C13 C12 121.31(13) . . ? C18 C13 C12 119.02(13) . . ? C15 C14 C13 119.75(13) . . ? C15 C14 H14 120.5(11) . . ? C13 C14 H14 119.7(11) . . ? C14 C15 C16 120.40(13) . . ? C14 C15 H15 118.6(10) . . ? C16 C15 H15 120.9(10) . . ? C17 C16 C15 119.81(12) . . ? C17 C16 C19 121.81(12) . . ? C15 C16 C19 118.38(12) . . ? C18 C17 C16 120.17(13) . . ? C18 C17 H17 119.5(11) . . ? C16 C17 H17 120.3(11) . . ? C17 C18 C13 120.20(13) . . ? C17 C18 H18 119.7(9) . . ? C13 C18 H18 120.0(9) . . ? O4 C19 O3 123.79(12) . . ? O4 C19 C16 123.96(13) . . ? O3 C19 C16 112.26(11) . . ? O3 C20 H201 108.4(11) . . ? O3 C20 H202 104.3(11) . . ? H201 C20 H202 111.7(15) . . ? O3 C20 H203 109.4(11) . . ? H201 C20 H203 112.3(16) . . ? H202 C20 H203 110.4(16) . . ? 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 C2 C3 C4 10.90(19) . . . . ? C15 C16 C19 O4 -12.7(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 C18 H18 O4 0.983(18) 2.299(18) 3.1584(19) 145.4(13) 1_655 _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.410 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.056 #===============================================END #==================================================END data_(5) _database_code_depnum_ccdc_archive 'CCDC 249326' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9,10-bis(4'-carbomethoxyphenylethynyl)anthracene ; _chemical_name_common 9,10-bis(4'-carbomethoxyphenylethynyl)anthracene _chemical_melting_point 549--551 _chemical_formula_moiety 'C34 H22 O4' _chemical_formula_sum 'C34 H22 O4' _chemical_formula_weight 494.52 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.225(1) _cell_length_b 11.660(1) _cell_length_c 15.381(1) _cell_angle_alpha 77.343(1) _cell_angle_beta 83.037(1) _cell_angle_gamma 72.026(1) _cell_volume 1200.5(1) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5483 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.53 cm. ; _diffrn_ambient_temperature 110(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 SMART CCD 1K area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 12771 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5483 _reflns_number_gt 4026 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'SMART version 5.054 (Bruker, 1998)' _computing_data_reduction 'SAINT version 6.01 (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. Methyl groups were refined as rigid bodies (with a common refined U for 3 hydrogens), other H atoms in 'riding' mode. ; _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^)+(0.0653P)^2^+0.1268P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5483 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.90595(14) 0.39055(8) 0.34656(5) 0.0240(2) Uani 1 1 d . . . O2 O 0.78815(14) 0.59644(8) 0.30859(6) 0.0276(2) Uani 1 1 d . . . C1 C 0.9667(2) 0.38528(13) 0.25401(8) 0.0264(3) Uani 1 1 d . . . H1A H 0.8523(10) 0.4109(8) 0.2190(3) 0.029(2) Uiso 1 1 d R . . H1B H 1.0412(13) 0.3016(7) 0.24913(12) 0.029(2) Uiso 1 1 d R . . H1C H 1.0473(13) 0.4398(8) 0.2316(3) 0.029(2) Uiso 1 1 d R . . C2 C 0.81950(18) 0.50326(11) 0.36458(8) 0.0198(3) Uani 1 1 d . . . C3 C 0.76894(18) 0.49836(11) 0.46194(7) 0.0182(3) Uani 1 1 d . . . C4 C 0.83363(18) 0.38969(11) 0.52424(8) 0.0199(3) Uani 1 1 d . . . H4 H 0.9111 0.3170 0.5045 0.024 Uiso 1 1 calc R . . C5 C 0.78582(18) 0.38715(11) 0.61437(8) 0.0209(3) Uani 1 1 d . . . H5 H 0.8296 0.3127 0.6562 0.025 Uiso 1 1 calc R . . C6 C 0.67292(18) 0.49415(11) 0.64407(8) 0.0194(3) Uani 1 1 d . . . C7 C 0.60944(19) 0.60328(11) 0.58137(8) 0.0207(3) Uani 1 1 d . . . H7 H 0.5339 0.6764 0.6010 0.025 Uiso 1 1 calc R . . C8 C 0.65587(18) 0.60533(11) 0.49124(8) 0.0202(3) Uani 1 1 d . . . H8 H 0.6109 0.6794 0.4492 0.024 Uiso 1 1 calc R . . C9 C 0.62275(19) 0.49324(12) 0.73757(8) 0.0215(3) Uani 1 1 d . . . C10 C 0.58334(18) 0.49459(12) 0.81508(8) 0.0218(3) Uani 1 1 d . . . C11 C 0.54028(18) 0.49755(12) 0.90792(8) 0.0202(3) Uani 1 1 d . . . C12 C 0.48048(18) 0.60914(12) 1.03174(8) 0.0203(3) Uani 1 1 d . . . C13 C 0.4601(2) 0.72032(12) 1.06130(9) 0.0243(3) Uani 1 1 d . . . H13 H 0.4318 0.7232 1.1229 0.029 Uiso 1 1 calc R . . C14 C 0.4805(2) 0.82255(13) 1.00285(9) 0.0277(3) Uani 1 1 d . . . H14 H 0.4664 0.8957 1.0239 0.033 Uiso 1 1 calc R . . C15 C 0.5228(2) 0.82000(12) 0.91059(9) 0.0266(3) Uani 1 1 d . . . H15 H 0.5379 0.8914 0.8703 0.032 Uiso 1 1 calc R . . C16 C 0.54176(19) 0.71619(12) 0.87947(8) 0.0232(3) Uani 1 1 d . . . H16 H 0.5690 0.7161 0.8175 0.028 Uiso 1 1 calc R . . C17 C 0.52130(18) 0.60701(12) 0.93873(8) 0.0204(3) Uani 1 1 d . . . O3 O 0.37334(14) 0.88428(8) 0.34817(5) 0.0235(2) Uani 1 1 d . . . O4 O 0.31806(15) 1.08900(9) 0.30836(6) 0.0293(2) Uani 1 1 d . . . C21 C 0.4358(2) 0.87286(13) 0.25661(8) 0.0266(3) Uani 1 1 d . . . H21A H 0.3270(10) 0.9136(8) 0.2190(4) 0.031(2) Uiso 1 1 d R . . H21B H 0.4827(13) 0.7868(7) 0.25272(14) 0.031(2) Uiso 1 1 d R . . H21C H 0.5396(13) 0.9106(8) 0.2368(3) 0.031(2) Uiso 1 1 d R . . C22 C 0.32049(18) 0.99872(12) 0.36488(8) 0.0202(3) Uani 1 1 d . . . C23 C 0.26799(17) 0.99928(11) 0.46172(7) 0.0184(3) Uani 1 1 d . . . C24 C 0.24907(18) 0.89406(12) 0.52140(8) 0.0202(3) Uani 1 1 d . . . H24 H 0.2692 0.8200 0.5005 0.024 Uiso 1 1 calc R . . C25 C 0.20113(19) 0.89702(12) 0.61084(8) 0.0222(3) Uani 1 1 d . . . H25 H 0.1862 0.8254 0.6509 0.027 Uiso 1 1 calc R . . C26 C 0.17437(18) 1.00502(11) 0.64282(8) 0.0190(3) Uani 1 1 d . . . C27 C 0.19580(18) 1.11043(12) 0.58252(8) 0.0206(3) Uani 1 1 d . . . H27 H 0.1795 1.1840 0.6034 0.025 Uiso 1 1 calc R . . C28 C 0.24049(18) 1.10717(11) 0.49304(8) 0.0201(3) Uani 1 1 d . . . H28 H 0.2526 1.1791 0.4525 0.024 Uiso 1 1 calc R . . C29 C 0.12461(18) 1.00760(12) 0.73587(8) 0.0214(3) Uani 1 1 d . . . C30 C 0.08470(18) 1.00702(12) 0.81371(8) 0.0219(3) Uani 1 1 d . . . C31 C 0.04020(18) 1.00403(12) 0.90711(8) 0.0205(3) Uani 1 1 d . . . C32 C -0.03204(18) 0.89243(12) 1.05669(8) 0.0204(3) Uani 1 1 d . . . C33 C -0.06156(19) 0.78291(12) 1.11135(8) 0.0242(3) Uani 1 1 d . . . H33 H -0.0900 0.7790 1.1737 0.029 Uiso 1 1 calc R . . C34 C -0.0495(2) 0.68395(13) 1.07521(9) 0.0277(3) Uani 1 1 d . . . H34 H -0.0701 0.6119 1.1126 0.033 Uiso 1 1 calc R . . C35 C -0.0068(2) 0.68730(13) 0.98256(9) 0.0283(3) Uani 1 1 d . . . H35 H 0.0026 0.6174 0.9582 0.034 Uiso 1 1 calc R . . C36 C 0.0210(2) 0.79064(13) 0.92814(8) 0.0250(3) Uani 1 1 d . . . H36 H 0.0490 0.7920 0.8660 0.030 Uiso 1 1 calc R . . C37 C 0.00899(18) 0.89670(12) 0.96272(8) 0.0211(3) 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 O1 0.0326(5) 0.0225(5) 0.0166(4) -0.0060(3) 0.0036(4) -0.0079(4) O2 0.0340(6) 0.0248(5) 0.0190(4) 0.0005(4) 0.0000(4) -0.0052(4) C1 0.0323(8) 0.0299(7) 0.0173(6) -0.0079(5) 0.0040(5) -0.0095(6) C2 0.0197(6) 0.0217(6) 0.0188(6) -0.0030(5) -0.0011(5) -0.0077(5) C3 0.0195(6) 0.0202(6) 0.0164(6) -0.0031(5) -0.0015(4) -0.0081(5) C4 0.0204(6) 0.0173(6) 0.0210(6) -0.0047(5) -0.0013(5) -0.0033(5) C5 0.0234(7) 0.0191(6) 0.0182(6) 0.0000(5) -0.0031(5) -0.0050(5) C6 0.0205(6) 0.0228(6) 0.0169(6) -0.0047(5) -0.0013(5) -0.0083(5) C7 0.0227(6) 0.0188(6) 0.0206(6) -0.0054(5) -0.0008(5) -0.0048(5) C8 0.0222(6) 0.0196(6) 0.0185(6) -0.0015(5) -0.0019(5) -0.0070(5) C9 0.0214(6) 0.0231(6) 0.0197(6) -0.0035(5) -0.0020(5) -0.0062(5) C10 0.0197(6) 0.0224(6) 0.0225(6) -0.0035(5) -0.0026(5) -0.0051(5) C11 0.0166(6) 0.0254(7) 0.0172(6) -0.0034(5) -0.0014(4) -0.0045(5) C12 0.0166(6) 0.0249(7) 0.0179(6) -0.0042(5) -0.0016(4) -0.0037(5) C13 0.0242(7) 0.0275(7) 0.0216(6) -0.0069(5) -0.0019(5) -0.0063(5) C14 0.0273(7) 0.0249(7) 0.0311(7) -0.0081(6) -0.0015(5) -0.0063(6) C15 0.0239(7) 0.0231(7) 0.0292(7) 0.0012(5) -0.0009(5) -0.0062(5) C16 0.0205(6) 0.0269(7) 0.0191(6) -0.0011(5) -0.0001(5) -0.0054(5) C17 0.0163(6) 0.0248(7) 0.0193(6) -0.0031(5) -0.0019(4) -0.0053(5) O3 0.0316(5) 0.0216(5) 0.0164(4) -0.0063(3) 0.0013(4) -0.0057(4) O4 0.0400(6) 0.0243(5) 0.0180(5) -0.0007(4) 0.0026(4) -0.0052(4) C21 0.0318(8) 0.0294(7) 0.0169(6) -0.0088(5) 0.0019(5) -0.0048(6) C22 0.0194(6) 0.0219(6) 0.0179(6) -0.0040(5) -0.0010(4) -0.0041(5) C23 0.0153(6) 0.0213(6) 0.0167(6) -0.0033(5) -0.0007(4) -0.0028(5) C24 0.0218(6) 0.0187(6) 0.0200(6) -0.0054(5) -0.0002(5) -0.0048(5) C25 0.0244(7) 0.0213(6) 0.0192(6) -0.0007(5) 0.0004(5) -0.0071(5) C26 0.0172(6) 0.0223(6) 0.0158(6) -0.0036(5) -0.0017(4) -0.0033(5) C27 0.0219(6) 0.0192(6) 0.0205(6) -0.0057(5) -0.0016(5) -0.0043(5) C28 0.0212(6) 0.0177(6) 0.0195(6) -0.0013(5) -0.0011(5) -0.0047(5) C29 0.0208(6) 0.0226(6) 0.0195(6) -0.0037(5) -0.0017(5) -0.0046(5) C30 0.0198(6) 0.0235(7) 0.0212(6) -0.0040(5) -0.0018(5) -0.0044(5) C31 0.0173(6) 0.0265(7) 0.0158(6) -0.0033(5) -0.0011(4) -0.0040(5) C32 0.0169(6) 0.0253(7) 0.0174(6) -0.0034(5) -0.0009(4) -0.0041(5) C33 0.0224(7) 0.0285(7) 0.0189(6) -0.0015(5) -0.0006(5) -0.0055(5) C34 0.0262(7) 0.0260(7) 0.0282(7) 0.0002(5) -0.0022(5) -0.0072(6) C35 0.0295(8) 0.0253(7) 0.0312(7) -0.0089(6) -0.0026(6) -0.0070(6) C36 0.0250(7) 0.0294(7) 0.0203(6) -0.0069(5) -0.0015(5) -0.0061(6) C37 0.0174(6) 0.0263(7) 0.0188(6) -0.0042(5) -0.0016(5) -0.0051(5) _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 C2 1.3436(15) . ? O1 C1 1.4467(14) . ? O2 C2 1.2077(15) . ? C2 C3 1.4907(16) . ? C3 C4 1.3976(17) . ? C3 C8 1.3981(17) . ? C4 C5 1.3835(17) . ? C5 C6 1.4008(18) . ? C6 C7 1.4032(17) . ? C6 C9 1.4385(16) . ? C7 C8 1.3830(17) . ? C9 C10 1.1940(18) . ? C10 C11 1.4298(17) . ? C11 C12 1.4165(17) 2_667 ? C11 C17 1.4189(18) . ? C12 C11 1.4166(17) 2_667 ? C12 C13 1.4260(18) . ? C12 C17 1.4293(17) . ? C13 C14 1.3629(19) . ? C14 C15 1.4197(19) . ? C15 C16 1.3598(19) . ? C16 C17 1.4311(17) . ? O3 C22 1.3434(15) . ? O3 C21 1.4477(14) . ? O4 C22 1.2064(15) . ? C22 C23 1.4927(16) . ? C23 C28 1.3936(17) . ? C23 C24 1.3950(17) . ? C24 C25 1.3826(17) . ? C25 C26 1.4013(18) . ? C26 C27 1.4063(17) . ? C26 C29 1.4373(16) . ? C27 C28 1.3813(17) . ? C29 C30 1.1960(18) . ? C30 C31 1.4288(17) . ? C31 C37 1.4166(18) . ? C31 C32 1.4191(18) 2_577 ? C32 C31 1.4191(18) 2_577 ? C32 C33 1.4273(18) . ? C32 C37 1.4328(17) . ? C33 C34 1.3621(19) . ? C34 C35 1.4156(19) . ? C35 C36 1.3637(19) . ? C36 C37 1.4249(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 C2 O1 C1 115.96(10) . . ? O2 C2 O1 123.90(11) . . ? O2 C2 C3 124.63(12) . . ? O1 C2 C3 111.47(10) . . ? C4 C3 C8 119.55(11) . . ? C4 C3 C2 121.41(11) . . ? C8 C3 C2 119.03(11) . . ? C5 C4 C3 120.54(11) . . ? C4 C5 C6 120.12(11) . . ? C5 C6 C7 119.17(11) . . ? C5 C6 C9 120.82(11) . . ? C7 C6 C9 120.00(11) . . ? C8 C7 C6 120.61(12) . . ? C7 C8 C3 120.01(11) . . ? C10 C9 C6 178.42(14) . . ? C9 C10 C11 178.48(14) . . ? C12 C11 C17 120.74(11) 2_667 . ? C12 C11 C10 119.70(12) 2_667 . ? C17 C11 C10 119.56(11) . . ? C11 C12 C13 121.56(11) 2_667 . ? C11 C12 C17 119.89(12) 2_667 . ? C13 C12 C17 118.55(12) . . ? C14 C13 C12 121.21(12) . . ? C13 C14 C15 120.19(13) . . ? C16 C15 C14 120.51(12) . . ? C15 C16 C17 120.97(12) . . ? C11 C17 C12 119.37(11) . . ? C11 C17 C16 122.06(11) . . ? C12 C17 C16 118.57(12) . . ? C22 O3 C21 115.94(10) . . ? O4 C22 O3 123.79(11) . . ? O4 C22 C23 124.71(12) . . ? O3 C22 C23 111.49(10) . . ? C28 C23 C24 119.54(11) . . ? C28 C23 C22 118.94(11) . . ? C24 C23 C22 121.51(11) . . ? C25 C24 C23 120.30(12) . . ? C24 C25 C26 120.43(11) . . ? C25 C26 C27 119.02(11) . . ? C25 C26 C29 120.20(11) . . ? C27 C26 C29 120.78(11) . . ? C28 C27 C26 120.14(12) . . ? C27 C28 C23 120.57(11) . . ? C30 C29 C26 178.58(14) . . ? C29 C30 C31 178.81(14) . . ? C37 C31 C32 120.83(11) . 2_577 ? C37 C31 C30 119.56(12) . . ? C32 C31 C30 119.60(11) 2_577 . ? C31 C32 C33 121.93(11) 2_577 . ? C31 C32 C37 119.41(11) 2_577 . ? C33 C32 C37 118.65(12) . . ? C34 C33 C32 120.80(12) . . ? C33 C34 C35 120.72(13) . . ? C36 C35 C34 120.15(13) . . ? C35 C36 C37 121.21(12) . . ? C31 C37 C36 121.77(11) . . ? C31 C37 C32 119.75(12) . . ? C36 C37 C32 118.46(12) . . ? 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 C2 C3 C4 8.75(16) . . . . ? O3 C22 C23 C24 -9.31(17) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.317 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.043