Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof Todd Marder' _publ_contact_author_address ; Department of Chemistry University of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email todd.marder@durham.ac.uk _publ_section_title ; Crystal engineering with p-substituted 4-ethynylbenzenes using the C-H...O supramolecular synthon ; loop_ _publ_author_name C.Dai Z.Yuan J.C.Collings T.M.Fasina R.Ll.Thomas K.P.Roscoe ; L.S.Stimson ; D.S.Yufit A.S.Batsanov J.A.K.Howard T.B.Marder #====================================================================== data_(1) _database_code_depnum_ccdc_archive 'CCDC 234595' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-methoxy-4-ethynylbenzene ; _chemical_name_common 1-methoxy-4-ethynylbenzene _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O' _chemical_formula_sum 'C9 H8 O' _chemical_formula_weight 132.15 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 14.027(5) _cell_length_b 6.124(2) _cell_length_c 17.047(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1464.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 665 _cell_measurement_theta_min 17.18 _cell_measurement_theta_max 30.20 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.077 _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 5 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 4.59 cm. ; _diffrn_ambient_temperature 100(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 10272 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 29.00 _reflns_number_total 1923 _reflns_number_gt 1705 _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 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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^)+(0.0510P)^2^+0.4494P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1923 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O O 0.39314(5) 0.67850(11) 0.28286(4) 0.02496(18) Uani 1 1 d . . . C1 C 0.38907(6) 0.58329(15) 0.35602(5) 0.0202(2) Uani 1 1 d . . . C2 C 0.34071(7) 0.67188(16) 0.42016(5) 0.0225(2) Uani 1 1 d . . . H2 H 0.3074(9) 0.812(2) 0.4157(7) 0.028(3) Uiso 1 1 d . . . C3 C 0.34065(6) 0.55886(16) 0.49149(6) 0.0230(2) Uani 1 1 d . . . H3 H 0.3072(9) 0.619(2) 0.5369(7) 0.029(3) Uiso 1 1 d . . . C4 C 0.38730(6) 0.35813(15) 0.49921(5) 0.0210(2) Uani 1 1 d . . . C5 C 0.43620(6) 0.27253(15) 0.43387(6) 0.0223(2) Uani 1 1 d . . . H5 H 0.4682(9) 0.134(2) 0.4383(7) 0.026(3) Uiso 1 1 d . . . C6 C 0.43733(6) 0.38431(15) 0.36312(5) 0.0222(2) Uani 1 1 d . . . H6 H 0.4714(10) 0.327(2) 0.3169(8) 0.035(3) Uiso 1 1 d . . . C7 C 0.33647(8) 0.87009(17) 0.26986(6) 0.0296(2) Uani 1 1 d . . . H71 H 0.3465(10) 0.912(3) 0.2138(9) 0.041(4) Uiso 1 1 d . . . H72 H 0.2666(11) 0.836(2) 0.2798(7) 0.038(4) Uiso 1 1 d . . . H73 H 0.3571(11) 0.994(3) 0.3038(9) 0.042(4) Uiso 1 1 d . . . C8 C 0.38541(6) 0.23946(17) 0.57219(6) 0.0239(2) Uani 1 1 d . . . C9 C 0.38368(7) 0.13613(18) 0.63188(6) 0.0285(2) Uani 1 1 d . . . H9 H 0.3848(10) 0.053(2) 0.6796(9) 0.040(4) 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 O 0.0297(4) 0.0256(3) 0.0195(3) 0.0012(3) 0.0019(3) 0.0025(3) C1 0.0196(4) 0.0221(4) 0.0191(4) -0.0009(3) -0.0008(3) -0.0035(3) C2 0.0229(4) 0.0213(4) 0.0232(4) -0.0021(3) 0.0011(3) 0.0013(3) C3 0.0219(4) 0.0259(5) 0.0211(4) -0.0031(3) 0.0024(3) 0.0003(3) C4 0.0182(4) 0.0240(4) 0.0207(4) -0.0008(3) -0.0013(3) -0.0028(3) C5 0.0214(4) 0.0213(4) 0.0243(4) -0.0015(3) -0.0008(3) 0.0016(3) C6 0.0214(4) 0.0241(4) 0.0211(4) -0.0036(3) 0.0017(3) 0.0009(3) C7 0.0371(6) 0.0249(5) 0.0267(5) 0.0031(4) -0.0001(4) 0.0035(4) C8 0.0215(4) 0.0260(4) 0.0243(4) -0.0015(3) -0.0005(3) -0.0009(4) C9 0.0297(5) 0.0312(5) 0.0245(5) 0.0017(4) 0.0007(4) 0.0003(4) _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 O C1 1.3778(11) . ? O C7 1.4345(13) . ? C1 C2 1.3964(13) . ? C1 C6 1.3992(13) . ? C2 C3 1.3991(14) . ? C2 H2 0.981(13) . ? C3 C4 1.3988(14) . ? C3 H3 0.978(13) . ? C4 C5 1.4092(13) . ? C4 C8 1.4410(13) . ? C5 C6 1.3869(13) . ? C5 H5 0.960(13) . ? C6 H6 0.986(14) . ? C7 H71 0.999(15) . ? C7 H72 1.016(15) . ? C7 H73 0.996(16) . ? C8 C9 1.1985(15) . ? C9 H9 0.960(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O C7 117.59(7) . . ? O C1 C2 124.36(9) . . ? O C1 C6 115.26(8) . . ? C2 C1 C6 120.38(9) . . ? C1 C2 C3 119.25(9) . . ? C1 C2 H2 120.8(7) . . ? C3 C2 H2 120.0(7) . . ? C4 C3 C2 121.08(8) . . ? C4 C3 H3 118.8(7) . . ? C2 C3 H3 120.1(7) . . ? C3 C4 C5 118.70(8) . . ? C3 C4 C8 121.05(8) . . ? C5 C4 C8 120.25(9) . . ? C6 C5 C4 120.62(9) . . ? C6 C5 H5 119.8(7) . . ? C4 C5 H5 119.6(7) . . ? C5 C6 C1 119.96(8) . . ? C5 C6 H6 121.6(8) . . ? C1 C6 H6 118.4(8) . . ? O C7 H71 106.4(9) . . ? O C7 H72 109.9(8) . . ? H71 C7 H72 110.4(11) . . ? O C7 H73 111.8(9) . . ? H71 C7 H73 108.5(12) . . ? H72 C7 H73 109.8(11) . . ? C9 C8 C4 178.41(11) . . ? C8 C9 H9 177.9(9) . . ? 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 C2 C1 O C7 -6.25(13) . . . . ? 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 C9 H9 O 0.960(15) 2.263(15) 3.2179(15) 173.0(12) 7_566 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.302 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.037 #=======================================================END data_(2) _database_code_depnum_ccdc_archive 'CCDC 234596' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(methoxycarbonyl)-4-ethynylbenzene ; _chemical_name_common 1-(methoxycarbonyl)-4-ethynylbenzene _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 O2' _chemical_formula_sum 'C10 H8 O2' _chemical_formula_weight 160.16 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 13.962(3) _cell_length_b 6.052(1) _cell_length_c 19.542(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1651.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 865 _cell_measurement_theta_min 12.13 _cell_measurement_theta_max 23.86 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.090 _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 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (15 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.43 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 18903 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 29.11 _reflns_number_total 2220 _reflns_number_gt 1817 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.049 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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^)+(0.0703P)^2^+0.3711P] 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 2220 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.65622(6) 0.11208(13) 0.68178(4) 0.0256(2) Uani 1 1 d . . . O2 O 0.58544(6) 0.39509(15) 0.73562(4) 0.0301(2) Uani 1 1 d . . . C1 C 0.61722(7) 0.42581(18) 0.61617(5) 0.0201(2) Uani 1 1 d . . . C2 C 0.65884(7) 0.33100(19) 0.55829(6) 0.0220(2) Uani 1 1 d . . . H2 H 0.6883(10) 0.189(3) 0.5615(7) 0.027(3) Uiso 1 1 d . . . C3 C 0.65699(7) 0.44255(19) 0.49650(6) 0.0233(2) Uani 1 1 d . . . H3 H 0.6850(10) 0.377(2) 0.4569(8) 0.031(4) Uiso 1 1 d . . . C4 C 0.61434(7) 0.65123(19) 0.49187(6) 0.0217(2) Uani 1 1 d . . . C5 C 0.57268(8) 0.74509(19) 0.55011(6) 0.0234(2) Uani 1 1 d . . . H5 H 0.5429(10) 0.890(2) 0.5472(7) 0.028(3) Uiso 1 1 d . . . C6 C 0.57384(8) 0.63306(18) 0.61166(6) 0.0228(2) Uani 1 1 d . . . H6 H 0.5432(11) 0.695(2) 0.6520(8) 0.030(3) Uiso 1 1 d . . . C7 C 0.61720(7) 0.31371(19) 0.68380(5) 0.0214(2) Uani 1 1 d . . . C8 C 0.61353(8) 0.77102(19) 0.42832(6) 0.0254(3) Uani 1 1 d . . . C9 C 0.61174(9) 0.8754(2) 0.37680(6) 0.0304(3) Uani 1 1 d . . . H9 H 0.6066(12) 0.955(3) 0.3356(9) 0.045(5) Uiso 1 1 d . . . C10 C 0.65550(9) -0.0071(2) 0.74611(6) 0.0291(3) Uani 1 1 d . . . H101 H 0.6816(12) -0.152(3) 0.7342(8) 0.041(4) Uiso 1 1 d . . . H102 H 0.6986(11) 0.071(3) 0.7793(8) 0.038(4) Uiso 1 1 d . . . H103 H 0.5892(11) -0.017(3) 0.7642(8) 0.036(4) 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 0.0269(4) 0.0234(4) 0.0266(4) 0.0038(3) 0.0028(3) 0.0037(3) O2 0.0356(5) 0.0322(5) 0.0225(4) -0.0032(3) 0.0007(3) 0.0057(4) C1 0.0163(5) 0.0216(5) 0.0225(5) -0.0014(4) -0.0012(4) -0.0016(4) C2 0.0185(5) 0.0205(5) 0.0270(5) -0.0021(4) 0.0017(4) 0.0008(4) C3 0.0199(5) 0.0261(5) 0.0239(5) -0.0027(4) 0.0020(4) 0.0000(4) C4 0.0167(5) 0.0247(5) 0.0238(5) 0.0000(4) -0.0018(4) -0.0036(4) C5 0.0224(5) 0.0204(5) 0.0273(5) -0.0016(4) -0.0027(4) 0.0016(4) C6 0.0213(5) 0.0232(5) 0.0238(5) -0.0043(4) -0.0008(4) 0.0015(4) C7 0.0172(5) 0.0229(5) 0.0240(5) -0.0020(4) -0.0019(4) -0.0010(4) C8 0.0214(5) 0.0273(6) 0.0276(6) -0.0009(5) -0.0009(4) -0.0015(4) C9 0.0299(6) 0.0341(6) 0.0273(6) 0.0033(5) 0.0011(5) 0.0007(5) C10 0.0277(6) 0.0292(6) 0.0304(6) 0.0091(5) 0.0015(5) 0.0015(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 C7 1.3370(13) . ? O1 C10 1.4495(14) . ? O2 C7 1.2102(13) . ? C1 C2 1.3951(15) . ? C1 C6 1.3957(15) . ? C1 C7 1.4856(15) . ? C2 C3 1.3836(16) . ? C2 H2 0.955(15) . ? C3 C4 1.3992(16) . ? C3 H3 0.953(16) . ? C4 C5 1.3987(16) . ? C4 C8 1.4381(16) . ? C5 C6 1.3808(16) . ? C5 H5 0.973(14) . ? C6 H6 0.972(15) . ? C8 C9 1.1889(17) . ? C9 H9 0.940(17) . ? C10 H101 0.980(18) . ? C10 H102 1.004(16) . ? C10 H103 0.993(15) . ? 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 C7 O1 C10 115.20(9) . . ? C2 C1 C6 119.94(10) . . ? C2 C1 C7 122.25(10) . . ? C6 C1 C7 117.81(10) . . ? C3 C2 C1 119.94(10) . . ? C3 C2 H2 120.4(9) . . ? C1 C2 H2 119.7(9) . . ? C2 C3 C4 120.32(10) . . ? C2 C3 H3 119.9(9) . . ? C4 C3 H3 119.8(9) . . ? C5 C4 C3 119.40(10) . . ? C5 C4 C8 119.65(10) . . ? C3 C4 C8 120.95(10) . . ? C6 C5 C4 120.30(10) . . ? C6 C5 H5 119.9(9) . . ? C4 C5 H5 119.8(9) . . ? C5 C6 C1 120.09(10) . . ? C5 C6 H6 120.9(9) . . ? C1 C6 H6 119.0(9) . . ? O2 C7 O1 123.06(10) . . ? O2 C7 C1 123.96(10) . . ? O1 C7 C1 112.98(9) . . ? C9 C8 C4 178.02(13) . . ? C8 C9 H9 176.6(11) . . ? O1 C10 H101 103.7(10) . . ? O1 C10 H102 108.8(9) . . ? H101 C10 H102 110.7(13) . . ? O1 C10 H103 110.2(9) . . ? H101 C10 H103 112.1(13) . . ? H102 C10 H103 111.0(12) . . ? 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 C9 H9 O2 0.940(17) 2.175(18) 3.1105(16) 173.2(15) 7_575 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.417 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 #=======================================================END data_(3) _database_code_depnum_ccdc_archive 'CCDC 234597' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-ethynylbenzaldehyde ; _chemical_name_common 4-ethynylbenzaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 O' _chemical_formula_sum 'C9 H6 O' _chemical_formula_weight 130.14 _chemical_absolute_configuration inapplicable 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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' _cell_length_a 7.0501(6) _cell_length_b 8.9204(8) _cell_length_c 10.7990(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 679.15(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4357 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 30.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 1.00 0.1300 0.00 1.00 -1.00 0.1300 1.00 0.00 0.00 0.1400 -1.00 0.00 0.00 0.1400 0.00 1.00 1.00 0.1250 0.00 -1.00 -1.00 0.1250 _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 (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.94 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 'Bruker ProteumM (APEX) CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 8531 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 30.49 _reflns_number_total 1215 _reflns_number_gt 1129 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.70 _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.28A (Bruker, 2002)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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^)+(0.0925P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.017(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'undeterminable, Friedel equivalents merged, all \Df" set to 0' _refine_ls_number_reflns 1215 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _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 O O 0.11344(17) 0.17049(12) 0.77337(8) 0.0345(3) Uani 1 1 d . . . C1 C 0.11276(16) 0.26697(13) 0.56699(9) 0.0205(2) Uani 1 1 d . . . C2 C 0.12461(17) 0.12829(15) 0.50704(10) 0.0219(3) Uani 1 1 d . . . H2 H 0.124(3) 0.034(2) 0.5575(16) 0.035(5) Uiso 1 1 d . . . C3 C 0.13194(19) 0.12227(12) 0.37885(10) 0.0219(3) Uani 1 1 d . . . H3 H 0.145(2) 0.021(2) 0.3366(15) 0.034(5) Uiso 1 1 d . . . C4 C 0.12736(15) 0.25544(14) 0.30909(11) 0.0202(2) Uani 1 1 d . . . C5 C 0.11653(18) 0.39471(12) 0.36997(10) 0.0226(3) Uani 1 1 d . . . H5 H 0.109(3) 0.4929(19) 0.3194(16) 0.031(4) Uiso 1 1 d . . . C6 C 0.10896(19) 0.39930(15) 0.49837(10) 0.0227(3) Uani 1 1 d . . . H6 H 0.102(3) 0.495(2) 0.5378(16) 0.030(4) Uiso 1 1 d . . . C7 C 0.10326(18) 0.27657(15) 0.70329(11) 0.0265(3) Uani 1 1 d . . . H7 H 0.086(3) 0.378(2) 0.7421(16) 0.029(4) Uiso 1 1 d . . . C8 C 0.13259(16) 0.24981(12) 0.17623(11) 0.0234(3) Uani 1 1 d . . . C9 C 0.13484(19) 0.24293(14) 0.06555(11) 0.0295(3) Uani 1 1 d . . . H9 H 0.133(2) 0.235(2) -0.0288(19) 0.045(6) 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 O 0.0412(5) 0.0452(6) 0.0170(4) 0.0034(3) -0.0007(4) 0.0094(5) C1 0.0195(5) 0.0264(5) 0.0155(5) 0.0000(4) -0.0008(4) 0.0012(5) C2 0.0248(5) 0.0240(5) 0.0169(5) 0.0023(4) 0.0001(4) 0.0015(5) C3 0.0273(6) 0.0217(5) 0.0167(5) -0.0004(3) -0.0002(4) 0.0019(5) C4 0.0200(4) 0.0244(5) 0.0161(4) 0.0011(4) 0.0004(4) -0.0003(5) C5 0.0271(5) 0.0220(5) 0.0187(5) 0.0019(4) -0.0009(4) 0.0001(5) C6 0.0279(5) 0.0224(5) 0.0178(5) -0.0025(3) -0.0011(4) 0.0000(5) C7 0.0253(5) 0.0376(7) 0.0165(5) -0.0026(4) -0.0017(4) 0.0030(5) C8 0.0273(5) 0.0240(5) 0.0189(5) 0.0007(4) 0.0002(4) -0.0016(6) C9 0.0389(7) 0.0304(6) 0.0192(6) 0.0011(4) 0.0002(5) -0.0025(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 O C7 1.2138(16) . ? C1 C6 1.3940(15) . ? C1 C2 1.3987(15) . ? C1 C7 1.4759(14) . ? C2 C3 1.3863(14) . ? C2 H2 0.998(18) . ? C3 C4 1.4070(15) . ? C3 H3 1.015(18) . ? C4 C5 1.4077(15) . ? C4 C8 1.4360(15) . ? C5 C6 1.3883(14) . ? C5 H5 1.033(17) . ? C6 H6 0.957(19) . ? C7 H7 1.006(18) . ? C8 C9 1.1969(17) . ? C9 H9 1.02(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 C6 C1 C2 120.27(9) . . ? C6 C1 C7 118.69(9) . . ? C2 C1 C7 121.04(10) . . ? C3 C2 C1 119.91(10) . . ? C3 C2 H2 120.8(11) . . ? C1 C2 H2 119.3(11) . . ? C2 C3 C4 120.07(11) . . ? C2 C3 H3 119.1(10) . . ? C4 C3 H3 120.8(10) . . ? C3 C4 C5 119.75(10) . . ? C3 C4 C8 120.32(10) . . ? C5 C4 C8 119.93(10) . . ? C6 C5 C4 119.65(10) . . ? C6 C5 H5 120.1(10) . . ? C4 C5 H5 120.2(10) . . ? C5 C6 C1 120.35(10) . . ? C5 C6 H6 118.2(11) . . ? C1 C6 H6 121.4(10) . . ? O C7 C1 125.02(11) . . ? O C7 H7 116.7(10) . . ? C1 C7 H7 118.3(10) . . ? C9 C8 C4 178.83(12) . . ? C8 C9 H9 178.0(11) . . ? 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 C2 C1 C7 O 3.5(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 C9 H9 O 1.02(2) 2.22(2) 3.2243(15) 168.9(17) 1_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.363 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.075 #=====================================================END data_(4) _database_code_depnum_ccdc_archive 'CCDC 234598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-ethynyl-2,3,5,6-tetrafluoroanisole ; _chemical_name_common 4-ethynyl-2,3,5,6-tetrafluoroanisole _chemical_melting_point 329--330 _chemical_formula_moiety 'C9 H4 F4 O' _chemical_formula_sum 'C9 H4 F4 O' _chemical_formula_weight 204.12 _chemical_absolute_configuration inapplicable 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.0302(6) _cell_length_b 6.240(1) _cell_length_c 8.220(1) _cell_angle_alpha 104.97(1) _cell_angle_beta 92.28(3) _cell_angle_gamma 91.73(1) _cell_volume 199.37(5) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 249 _cell_measurement_theta_min 10 _cell_measurement_theta_max 23 _exptl_crystal_description block _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 102 _exptl_absorpt_coefficient_mu 0.173 _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 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 32 duplicate reflections. Crystal to detector distance 4.60 cm. Besides unique reflections, 232 Friedel equivalents were measured, of which 222 were observed. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 1438 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.47 _reflns_number_total 897 _reflns_number_gt 835 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.80 _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 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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^)+(0.0570P)^2^+0.0497P] 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_abs_structure_details 'undeterminable, Friedel pairs merged, all \Df" set to 0' _refine_ls_number_reflns 897 _refine_ls_number_parameters 144 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_restrained_S_all 1.252 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.002 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 F2 F 0.0812(6) 0.6961(4) 0.3631(3) 0.0294(6) Uani 1 1 d . . . F3 F 0.3024(6) 0.9191(4) 0.6759(3) 0.0280(6) Uani 1 1 d . . . F5 F 0.8600(6) 0.2860(4) 0.7362(3) 0.0288(6) Uani 1 1 d . . . F6 F 0.6504(6) 0.0659(4) 0.4209(3) 0.0282(6) Uani 1 1 d . . . O O 0.2429(7) 0.2563(4) 0.2292(3) 0.0270(7) Uani 1 1 d . . . C1 C 0.3610(10) 0.3758(6) 0.3846(5) 0.0205(8) Uani 1 1 d . . . C2 C 0.2788(10) 0.5957(7) 0.4533(5) 0.0222(8) Uani 1 1 d . . . C3 C 0.3916(10) 0.7106(6) 0.6150(5) 0.0208(8) Uani 1 1 d . . . C4 C 0.5881(10) 0.6098(6) 0.7157(4) 0.0200(8) Uani 1 1 d . . . C5 C 0.6671(9) 0.3899(6) 0.6456(4) 0.0200(8) Uani 1 1 d . . . C6 C 0.5593(10) 0.2765(6) 0.4836(5) 0.0202(8) Uani 1 1 d . . . C7 C 0.3705(9) 0.3281(6) 0.0885(4) 0.0289(7) Uani 1 1 d . . . H71 H 0.624(13) 0.329(8) 0.096(6) 0.039(13) Uiso 1 1 d . . . H72 H 0.316(17) 0.474(12) 0.095(8) 0.068(19) Uiso 1 1 d . . . H73 H 0.261(16) 0.204(11) -0.019(9) 0.064(17) Uiso 1 1 d . . . C8 C 0.7130(10) 0.7287(6) 0.8817(5) 0.0229(8) Uani 1 1 d . . . C9 C 0.8235(10) 0.8272(6) 1.0177(5) 0.0304(7) Uani 1 1 d . . . H9 H 0.913(16) 0.928(11) 1.132(8) 0.067(19) 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 F2 0.0327(14) 0.0309(13) 0.0250(11) 0.0081(10) -0.0057(10) 0.0085(10) F3 0.0352(14) 0.0203(12) 0.0269(11) 0.0026(9) 0.0042(10) 0.0062(9) F5 0.0313(13) 0.0294(13) 0.0262(11) 0.0085(9) -0.0069(9) 0.0078(10) F6 0.0424(15) 0.0161(11) 0.0232(11) -0.0009(9) 0.0037(10) 0.0066(9) O 0.0340(17) 0.0279(17) 0.0166(12) 0.0029(11) -0.0026(11) -0.0081(13) C1 0.022(2) 0.021(2) 0.0163(16) 0.0030(14) 0.0011(14) -0.0028(14) C2 0.020(2) 0.026(2) 0.0212(18) 0.0080(16) -0.0017(15) 0.0006(14) C3 0.022(2) 0.0170(18) 0.0222(18) 0.0034(14) 0.0028(15) 0.0023(14) C4 0.0204(19) 0.0215(19) 0.0161(16) 0.0020(14) 0.0002(14) -0.0033(13) C5 0.021(2) 0.021(2) 0.0183(17) 0.0061(15) -0.0004(15) 0.0015(14) C6 0.022(2) 0.018(2) 0.0185(16) 0.0010(13) 0.0034(14) -0.0011(14) C7 0.0354(19) 0.0320(18) 0.0187(15) 0.0059(13) 0.0002(13) 0.0018(14) C8 0.029(2) 0.0197(18) 0.0181(17) 0.0018(15) -0.0013(15) -0.0019(15) C9 0.0392(19) 0.0270(16) 0.0224(16) 0.0029(13) -0.0042(13) -0.0025(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 F2 C2 1.341(5) . ? F3 C3 1.333(5) . ? F5 C5 1.347(5) . ? F6 C6 1.350(5) . ? O C1 1.361(5) . ? O C7 1.451(4) . ? C1 C6 1.387(5) . ? C1 C2 1.398(6) . ? C2 C3 1.388(5) . ? C3 C4 1.399(5) . ? C4 C5 1.396(6) . ? C4 C8 1.437(5) . ? C5 C6 1.382(5) . ? C7 H71 1.02(5) . ? C7 H72 0.93(7) . ? C7 H73 1.08(7) . ? C8 C9 1.190(5) . ? C9 H9 1.03(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O C7 115.4(3) . . ? O C1 C6 119.9(3) . . ? O C1 C2 122.4(4) . . ? C6 C1 C2 117.7(3) . . ? F2 C2 C3 119.3(4) . . ? F2 C2 C1 119.5(4) . . ? C3 C2 C1 121.1(4) . . ? F3 C3 C2 118.9(4) . . ? F3 C3 C4 119.8(3) . . ? C2 C3 C4 121.2(3) . . ? C5 C4 C3 116.9(3) . . ? C5 C4 C8 121.3(4) . . ? C3 C4 C8 121.7(4) . . ? F5 C5 C6 118.7(4) . . ? F5 C5 C4 119.4(3) . . ? C6 C5 C4 121.9(3) . . ? F6 C6 C5 119.3(4) . . ? F6 C6 C1 119.6(3) . . ? C5 C6 C1 121.1(3) . . ? O C7 H71 109(3) . . ? O C7 H72 111(4) . . ? H71 C7 H72 106(5) . . ? O C7 H73 102(4) . . ? H71 C7 H73 113(5) . . ? H72 C7 H73 116(6) . . ? C9 C8 C4 178.5(4) . . ? C8 C9 H9 174(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C4 O C9 129(5) . . . . ? 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 C9 H9 O 1.03(7) 2.35(7) 3.184(4) 138(5) 1_666 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.284 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.047 #=======================================================END data_(5) _database_code_depnum_ccdc_archive 'CCDC 234599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-ethynylthioanisole ; _chemical_name_common 4-ethynylthioanisole _chemical_melting_point 290--291 _chemical_formula_moiety 'C9 H8 S' _chemical_formula_sum 'C9 H8 S' _chemical_formula_weight 148.21 _chemical_absolute_configuration inapplicable 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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' _cell_length_a 5.646(1) _cell_length_b 7.268(1) _cell_length_c 19.528(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 801.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 707 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 28.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.320 _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 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. ; _diffrn_ambient_temperature 120(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 6000' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 6423 _diffrn_reflns_av_R_equivalents 0.1071 _diffrn_reflns_av_sigmaI/netI 0.1362 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1940 _reflns_number_gt 1032 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.67 _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.26(16) _refine_ls_number_reflns 1940 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 S S 0.06460(18) 0.09816(16) 0.89501(5) 0.0379(3) Uani 1 1 d . . . C1 C 0.1753(6) 0.1279(5) 0.81134(17) 0.0261(9) Uani 1 1 d . . . C2 C 0.3933(6) 0.2104(5) 0.79563(18) 0.0277(9) Uani 1 1 d . . . H2 H 0.4914 0.2550 0.8315 0.033 Uiso 1 1 calc R . . C3 C 0.4665(6) 0.2274(4) 0.72839(17) 0.0269(9) Uani 1 1 d . . . H3 H 0.6142 0.2841 0.7186 0.032 Uiso 1 1 calc R . . C4 C 0.3263(6) 0.1621(5) 0.67447(19) 0.0270(9) Uani 1 1 d . . . C5 C 0.1094(6) 0.0808(5) 0.69046(17) 0.0283(9) Uani 1 1 d . . . H5 H 0.0113 0.0361 0.6546 0.034 Uiso 1 1 calc R . . C6 C 0.0349(7) 0.0641(4) 0.75773(18) 0.0278(9) Uani 1 1 d . . . H6 H -0.1137 0.0086 0.7674 0.033 Uiso 1 1 calc R . . C7 C 0.3056(9) 0.1742(7) 0.9481(3) 0.0424(12) Uani 1 1 d . . . H71 H 0.444(8) 0.084(6) 0.9377(19) 0.068(14) Uiso 1 1 d . . . H72 H 0.260(6) 0.143(5) 0.9997(18) 0.046(12) Uiso 1 1 d . . . H73 H 0.351(5) 0.305(6) 0.9429(16) 0.030(11) Uiso 1 1 d . . . C8 C 0.4081(7) 0.1774(5) 0.6052(2) 0.0329(9) Uani 1 1 d . . . C9 C 0.4787(8) 0.1890(6) 0.5493(3) 0.0463(12) Uani 1 1 d . . . H9 H 0.533(9) 0.198(6) 0.503(2) 0.102(19) 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 S 0.0364(5) 0.0418(6) 0.0355(5) 0.0039(6) 0.0002(5) -0.0038(6) C1 0.0258(19) 0.025(2) 0.027(2) -0.0012(18) -0.0023(16) 0.0053(17) C2 0.026(2) 0.023(2) 0.034(2) 0.0021(18) -0.0076(17) -0.0024(17) C3 0.020(2) 0.0177(19) 0.043(2) 0.0042(17) -0.0037(17) 0.0023(17) C4 0.029(2) 0.018(2) 0.034(2) 0.0045(18) 0.0022(17) 0.0037(16) C5 0.026(2) 0.024(2) 0.035(2) 0.0001(19) -0.0074(16) 0.0049(19) C6 0.0193(19) 0.020(2) 0.044(2) 0.0042(17) 0.0015(17) -0.0035(18) C7 0.050(3) 0.040(3) 0.037(3) 0.000(2) -0.005(2) -0.010(3) C8 0.035(2) 0.028(2) 0.036(2) -0.003(2) 0.000(2) 0.0027(19) C9 0.056(3) 0.040(3) 0.043(3) -0.001(2) 0.004(2) -0.006(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 S C1 1.763(3) . ? S C7 1.797(4) . ? C1 C6 1.393(5) . ? C1 C2 1.403(4) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.400(4) . ? C3 H3 0.9500 . ? C4 C5 1.395(5) . ? C4 C8 1.433(5) . ? C5 C6 1.385(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H71 1.04(4) . ? C7 H72 1.06(3) . ? C7 H73 0.99(4) . ? C8 C9 1.166(5) . ? C9 H9 0.95(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 C1 S C7 103.2(2) . . ? C6 C1 C2 118.5(3) . . ? C6 C1 S 117.0(3) . . ? C2 C1 S 124.5(3) . . ? C3 C2 C1 120.5(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.1(3) . . ? C5 C4 C8 121.8(3) . . ? C3 C4 C8 120.1(3) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.7(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? S C7 H71 105(2) . . ? S C7 H72 107.4(19) . . ? H71 C7 H72 104(3) . . ? S C7 H73 115.7(19) . . ? H71 C7 H73 113(3) . . ? H72 C7 H73 111(3) . . ? C9 C8 C4 178.8(5) . . ? C8 C9 H9 179(3) . . ? 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 C9 H9 S 0.95(4) 3.07(5) 3.673(5) 123(3) 2_554 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.321 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.070 #=================================================END data_(6) _database_code_depnum_ccdc_archive 'CCDC 234600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-ethynyltoluene ; _chemical_name_common 4-ethynyltoluene _chemical_melting_point ? _chemical_formula_moiety 'C9 H8' _chemical_formula_sum 'C9 H8' _chemical_formula_weight 116.15 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.9008(5) _cell_length_b 10.0652(8) _cell_length_c 11.6577(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.919(3) _cell_angle_gamma 90.00 _cell_volume 674.86(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1017 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 29.19 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.064 _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 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. ; _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 'Bruker Proteum-M (APEX) CCD area detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 5257 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 28.99 _reflns_number_total 1770 _reflns_number_gt 1187 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.28A (Bruker, 2002)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1770 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 C1 C 0.3524(2) 0.24039(12) 0.45434(11) 0.0221(3) Uani 1 1 d . . . C2 C 0.5821(2) 0.27202(13) 0.50591(11) 0.0233(3) Uani 1 1 d . . . H2 H 0.663(2) 0.2258(14) 0.5779(12) 0.036(4) Uiso 1 1 d . . . C3 C 0.7023(2) 0.36908(12) 0.46018(11) 0.0217(3) Uani 1 1 d . . . H3 H 0.864(2) 0.3930(13) 0.4982(10) 0.026(4) Uiso 1 1 d . . . C4 C 0.5921(2) 0.43902(11) 0.35915(10) 0.0192(3) Uani 1 1 d . . . C5 C 0.3606(2) 0.41015(13) 0.30803(11) 0.0214(3) Uani 1 1 d . . . H5 H 0.280(2) 0.4607(13) 0.2385(10) 0.021(3) Uiso 1 1 d . . . C6 C 0.2433(2) 0.31215(13) 0.35456(11) 0.0232(3) Uani 1 1 d . . . H6 H 0.081(2) 0.2919(12) 0.3168(10) 0.024(4) Uiso 1 1 d . . . C7 C 0.2248(3) 0.13368(16) 0.50467(15) 0.0318(4) Uani 1 1 d . . . H71 H 0.313(3) 0.055(2) 0.5213(15) 0.077(6) Uiso 1 1 d . . . H72 H 0.193(3) 0.1576(18) 0.5781(17) 0.075(6) Uiso 1 1 d . . . H73 H 0.071(4) 0.112(2) 0.4542(17) 0.086(7) Uiso 1 1 d . . . C8 C 0.7180(2) 0.53744(13) 0.30874(11) 0.0217(3) Uani 1 1 d . . . C9 C 0.8248(2) 0.61582(14) 0.26623(11) 0.0274(3) Uani 1 1 d . . . H9 H 0.916(3) 0.6773(15) 0.2330(12) 0.045(4) 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 C1 0.0268(8) 0.0187(7) 0.0235(7) -0.0043(5) 0.0113(6) -0.0012(6) C2 0.0285(8) 0.0225(7) 0.0190(7) 0.0014(5) 0.0058(6) 0.0015(6) C3 0.0211(8) 0.0219(7) 0.0215(7) -0.0025(5) 0.0034(6) -0.0007(6) C4 0.0217(7) 0.0161(6) 0.0207(6) -0.0032(5) 0.0070(5) 0.0003(5) C5 0.0226(7) 0.0207(7) 0.0204(6) -0.0002(5) 0.0039(5) 0.0022(6) C6 0.0182(8) 0.0247(7) 0.0267(7) -0.0043(6) 0.0048(6) -0.0016(6) C7 0.0364(10) 0.0264(9) 0.0362(9) 0.0011(7) 0.0159(8) -0.0047(7) C8 0.0218(7) 0.0224(7) 0.0209(6) -0.0012(5) 0.0045(5) 0.0031(6) C9 0.0273(8) 0.0272(8) 0.0281(7) 0.0037(6) 0.0067(6) -0.0007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3913(18) . ? C1 C6 1.3980(17) . ? C1 C7 1.5041(19) . ? C2 C3 1.3823(18) . ? C2 H2 0.985(14) . ? C3 C4 1.4010(16) . ? C3 H3 0.986(13) . ? C4 C5 1.3938(17) . ? C4 C8 1.4399(18) . ? C5 C6 1.3836(18) . ? C5 H5 0.986(12) . ? C6 H6 0.981(13) . ? C7 H71 0.95(2) . ? C7 H72 0.95(2) . ? C7 H73 0.99(2) . ? C8 C9 1.1854(18) . ? C9 H9 0.956(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117.67(12) . . ? C2 C1 C7 121.28(13) . . ? C6 C1 C7 121.05(14) . . ? C3 C2 C1 121.96(13) . . ? C3 C2 H2 118.0(8) . . ? C1 C2 H2 120.1(8) . . ? C2 C3 C4 119.85(13) . . ? C2 C3 H3 121.7(7) . . ? C4 C3 H3 118.4(7) . . ? C5 C4 C3 118.75(12) . . ? C5 C4 C8 120.97(12) . . ? C3 C4 C8 120.28(12) . . ? C6 C5 C4 120.63(12) . . ? C6 C5 H5 119.9(7) . . ? C4 C5 H5 119.5(7) . . ? C5 C6 C1 121.12(13) . . ? C5 C6 H6 119.7(7) . . ? C1 C6 H6 119.2(7) . . ? C1 C7 H71 112.4(11) . . ? C1 C7 H72 112.8(11) . . ? H71 C7 H72 103.7(15) . . ? C1 C7 H73 113.5(11) . . ? H71 C7 H73 108.7(15) . . ? H72 C7 H73 104.8(15) . . ? C9 C8 C4 178.25(14) . . ? C8 C9 H9 178.1(9) . . ? 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 C9 H9 C5 0.956(15) 2.783(15) 3.700(2) 161.0(11) 2_655 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.222 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.041 #=======================================================END