# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_method 'SHELXL-97 plus manual editing' _journal_coden_Cambridge 182 loop_ _publ_author_name 'Bond, Andrew' _publ_contact_author_name 'Dr Andrew D. Bond' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UK ; _publ_contact_author_email adb29@cam.ac.uk _publ_contact_author_fax '(01223) 336362' _publ_contact_author_phone '(01223) 336352' _publ_requested_journal 'Chemical Communications' _publ_section_title ; The influence of C-H...pi interactions in the low-temperature crystal structures of a,w-unsaturated linear hydrocarbons ; data_1 _database_code_CSD 183117 _chemical_name_systematic 1,7-octadiene _chemical_name_common 1,7-octadiene _chemical_melting_point ? _chemical_formula_moiety 'C8 H14' _chemical_formula_sum 'C8 H14' _chemical_formula_weight 110.19 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3210(16) _cell_length_b 4.9140(5) _cell_length_c 8.7545(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.510(6) _cell_angle_gamma 90.00 _cell_volume 395.47(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3760 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_rad 0.15 _exptl_crystal_size_length 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.925 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 124 _exptl_absorpt_coefficient_mu 0.051 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary at 162.2 K ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 1752 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 25.02 _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.891 _reflns_number_total 620 _reflns_number_gt 552 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.0419P] 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 620 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.104 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.019 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 0.61378(14) 0.2388(3) 0.63859(16) 0.0563(5) Uani 1 1 d . . . H1A H 0.5655(17) 0.326(3) 0.7187(18) 0.067(4) Uiso 1 1 d . . . H1B H 0.5702(17) 0.264(3) 0.529(2) 0.071(4) Uiso 1 1 d . . . C2 C 0.72950(13) 0.0869(2) 0.67341(13) 0.0471(5) Uani 1 1 d . . . H2A H 0.7710(16) 0.068(3) 0.781(2) 0.060(4) Uiso 1 1 d . . . C3 C 0.80795(12) -0.0503(2) 0.55894(13) 0.0432(5) Uani 1 1 d . . . H3A H 0.7519(14) -0.037(2) 0.4548(17) 0.045(3) Uiso 1 1 d . . . H3B H 0.8172(16) -0.248(3) 0.5847(15) 0.059(4) Uiso 1 1 d . . . C4 C 0.96005(11) 0.0662(2) 0.55936(12) 0.0414(5) Uani 1 1 d . . . H4A H 0.9513(14) 0.263(3) 0.5376(15) 0.055(4) Uiso 1 1 d . . . H4B H 1.0163(15) 0.048(2) 0.6620(18) 0.049(3) 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 0.0551(8) 0.0576(9) 0.0576(9) -0.0044(6) 0.0140(6) 0.0027(5) C2 0.0504(8) 0.0489(8) 0.0422(8) 0.0014(4) 0.0085(5) -0.0031(5) C3 0.0478(8) 0.0375(7) 0.0437(8) 0.0003(4) 0.0062(6) -0.0012(4) C4 0.0469(8) 0.0348(7) 0.0415(8) -0.0015(4) 0.0043(6) 0.0000(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 C1 C2 1.306(2) . ? C1 H1B 0.98(2) . ? C1 H1A 0.99(2) . ? C2 C3 1.495(2) . ? C2 H2A 0.96(2) . ? C3 C4 1.528(2) . ? C3 H3A 0.98(2) . ? C3 H3B 1.00(2) . ? C4 C4 1.521(2) 3_756 ? C4 H4A 0.99(2) . ? C4 H4B 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 C1 H1B 119.4(9) . . ? C2 C1 H1A 122.4(9) . . ? H1B C1 H1A 118.1(13) . . ? C1 C2 C3 125.30(11) . . ? C1 C2 H2A 118.0(9) . . ? C3 C2 H2A 116.7(9) . . ? C2 C3 C4 112.70(9) . . ? C2 C3 H3A 110.5(7) . . ? C4 C3 H3A 109.3(7) . . ? C2 C3 H3B 108.7(8) . . ? C4 C3 H3B 108.5(8) . . ? H3A C3 H3B 106.9(10) . . ? C4 C4 C3 113.40(11) 3_756 . ? C4 C4 H4A 108.7(8) 3_756 . ? C3 C4 H4A 108.6(8) . . ? C4 C4 H4B 110.1(8) 3_756 . ? C3 C4 H4B 109.2(8) . . ? H4A C4 H4B 106.6(10) . . ? 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 C1 C2 C3 C4 112.96(14) . . . . ? C2 C3 C4 C4 -178.52(10) . . . 3_756 ? #===END data_2 _database_code_CSD 183118 _chemical_name_systematic 1,9-decadiene _chemical_name_common 1,9-decadiene _chemical_melting_point ? _chemical_formula_moiety 'C10 H18' _chemical_formula_sum 'C10 H18' _chemical_formula_weight 138.24 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.648(2) _cell_length_b 4.9005(8) _cell_length_c 8.819(1) _cell_angle_alpha 90.00 _cell_angle_beta 105.31(1) _cell_angle_gamma 90.00 _cell_volume 485.53(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16176 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 156 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in 0.3 mm glass capillary at 296.0 K. Diffraction pattern contained contributions from several crystals (reflected in high R~int~). Only reflections associated with the major crystal were included in the integration. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 3444 _diffrn_reflns_av_R_equivalents 0.1830 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.54 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.981 _reflns_number_total 1091 _reflns_number_gt 857 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1010P)^2^+0.0975P] 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 0.40(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1091 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.2366 _refine_ls_wR_factor_gt 0.2187 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.266 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.046 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 0.59284(19) 0.2340(4) 0.6522(2) 0.0521(7) Uani 1 1 d . . . H1A H 0.558(2) 0.324(6) 0.725(3) 0.068(7) Uiso 1 1 d . . . H1B H 0.556(2) 0.268(5) 0.538(3) 0.060(6) Uiso 1 1 d . . . C2 C 0.68743(16) 0.0807(4) 0.6975(2) 0.0424(6) Uani 1 1 d . . . H2 H 0.720(2) 0.053(5) 0.807(3) 0.057(6) Uiso 1 1 d . . . C3 C 0.75037(16) -0.0537(3) 0.5890(2) 0.0384(6) Uani 1 1 d . . . H3A H 0.7050(17) -0.035(4) 0.482(2) 0.036(5) Uiso 1 1 d . . . H3B H 0.756(2) -0.249(5) 0.608(3) 0.055(6) Uiso 1 1 d . . . C4 C 0.87453(15) 0.0651(3) 0.60586(18) 0.0365(6) Uani 1 1 d . . . H4A H 0.871(2) 0.254(6) 0.586(3) 0.052(6) Uiso 1 1 d . . . H4B H 0.920(2) 0.048(4) 0.713(3) 0.042(5) Uiso 1 1 d . . . C5 C 0.93856(15) -0.0603(3) 0.49246(18) 0.0361(6) Uani 1 1 d . . . H5A H 0.8901(19) -0.036(4) 0.385(3) 0.044(5) Uiso 1 1 d . . . H5B H 0.9458(18) -0.258(5) 0.514(2) 0.044(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 C1 0.0571(12) 0.0517(13) 0.0525(12) -0.0064(8) 0.0236(9) 0.0008(8) C2 0.0534(11) 0.0415(11) 0.0370(10) -0.0003(6) 0.0202(7) -0.0044(7) C3 0.0501(10) 0.0294(10) 0.0386(10) 0.0001(6) 0.0166(7) -0.0011(6) C4 0.0494(10) 0.0292(10) 0.0333(10) -0.0015(6) 0.0150(7) -0.0001(6) C5 0.0489(11) 0.0276(11) 0.0340(10) -0.0012(6) 0.0148(7) 0.0001(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 1.306(3) . ? C1 H1A 0.95(3) . ? C1 H1B 1.00(2) . ? C2 C3 1.502(2) . ? C2 H2 0.95(2) . ? C3 C4 1.529(2) . ? C3 H3A 0.96(2) . ? C3 H3B 0.97(3) . ? C4 C5 1.526(2) . ? C4 H4A 0.94(3) . ? C4 H4B 0.96(2) . ? C5 C5 1.522(3) 3_756 ? C5 H5A 0.97(2) . ? C5 H5B 0.98(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 122.3(15) . . ? C2 C1 H1B 120.6(14) . . ? H1A C1 H1B 117(2) . . ? C1 C2 C3 124.86(16) . . ? C1 C2 H2 118.5(14) . . ? C3 C2 H2 116.7(14) . . ? C2 C3 C4 112.27(14) . . ? C2 C3 H3A 110.6(12) . . ? C4 C3 H3A 108.8(12) . . ? C2 C3 H3B 109.9(15) . . ? C4 C3 H3B 109.8(15) . . ? H3A C3 H3B 105.2(18) . . ? C5 C4 C3 113.33(14) . . ? C5 C4 H4A 106.4(15) . . ? C3 C4 H4A 111.2(15) . . ? C5 C4 H4B 111.9(14) . . ? C3 C4 H4B 109.1(14) . . ? H4A C4 H4B 104.6(18) . . ? C5 C5 C4 113.42(17) 3_756 . ? C5 C5 H5A 109.1(13) 3_756 . ? C4 C5 H5A 109.3(13) . . ? C5 C5 H5B 109.5(13) 3_756 . ? C4 C5 H5B 107.7(13) . . ? H5A C5 H5B 107.7(17) . . ? 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 C1 C2 C3 C4 112.8(2) . . . . ? C2 C3 C4 C5 -177.79(13) . . . . ? C3 C4 C5 C5 179.21(15) . . . 3_756 ? #===END data_3 _database_code_CSD 183119 _chemical_name_systematic 1,7-octadiyne _chemical_name_common 1,7-octadyine _chemical_melting_point ? _chemical_formula_moiety 'C8 H10' _chemical_formula_sum 'C8 H10' _chemical_formula_weight 106.16 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 7.0594(2) _cell_length_b 5.9531(2) _cell_length_c 16.7430(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 703.63(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16085 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 24.94 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.002 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.056 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in-situ in a 0.3 mm glass capillary at 241.0 K. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 1086 _diffrn_reflns_av_R_equivalents 0.0105 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 24.94 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 609 _reflns_number_gt 543 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.0772P] 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 609 _refine_ls_number_parameters 57 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.129 _refine_diff_density_min -0.114 _refine_diff_density_rms 0.023 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 0.57613(18) 0.49194(19) 0.18004(6) 0.0447(4) Uani 1 1 d . . . H1 H 0.622(2) 0.622(2) 0.2062(9) 0.063(4) Uiso 1 1 d . . . C2 C 0.51860(14) 0.32995(18) 0.14675(6) 0.0368(3) Uani 1 1 d . . . C3 C 0.45108(15) 0.12957(19) 0.10479(6) 0.0376(4) Uani 1 1 d . . . H3A H 0.3159(19) 0.1365(18) 0.1006(6) 0.044(3) Uiso 1 1 d . . . H3B H 0.4823(17) -0.008(2) 0.1367(7) 0.043(3) Uiso 1 1 d . . . C4 C 0.53734(13) 0.10321(18) 0.02150(6) 0.0351(3) Uani 1 1 d . . . H4A H 0.5070(15) 0.239(2) -0.0110(7) 0.044(3) Uiso 1 1 d . . . H4B H 0.6749(19) 0.0917(18) 0.0264(6) 0.042(3) 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 0.0559(7) 0.0377(7) 0.0404(6) -0.0009(5) 0.0039(5) -0.0004(5) C2 0.0399(6) 0.0375(6) 0.0331(5) 0.0045(4) 0.0031(4) 0.0034(4) C3 0.0393(7) 0.0372(7) 0.0363(6) 0.0017(4) 0.0004(4) -0.0038(4) C4 0.0335(6) 0.0365(7) 0.0353(6) 0.0020(5) -0.0008(4) -0.0023(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 C1 C2 1.186(2) . ? C1 H1 0.95(2) . ? C2 C3 1.464(2) . ? C3 C4 1.530(1) . ? C3 H3A 0.96(1) . ? C3 H3B 1.00(1) . ? C4 C4 1.519(2) 5_655 ? C4 H4A 1.00(1) . ? C4 H4B 0.98(1) . ? 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 H1 179.4(9) . . ? C1 C2 C3 178.88(11) . . ? C2 C3 C4 113.04(8) . . ? C2 C3 H3A 109.0(7) . . ? C4 C3 H3A 109.5(7) . . ? C2 C3 H3B 109.7(7) . . ? C4 C3 H3B 108.4(7) . . ? H3A C3 H3B 107.1(9) . . ? C4 C4 C3 112.15(10) 5_655 . ? C4 C4 H4A 108.8(7) 5_655 . ? C3 C4 H4A 109.2(7) . . ? C4 C4 H4B 109.2(6) 5_655 . ? C3 C4 H4B 109.0(6) . . ? H4A C4 H4B 108.4(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 C3 C4 C4 -178.95(10) . . . 5_655 ? #===END data_4 _database_code_CSD 183120 _chemical_name_systematic 1,9-decadiyne _chemical_name_common 1,9-decadiyne _chemical_melting_point ? _chemical_formula_moiety 'C10 H14' _chemical_formula_sum 'C10 H14' _chemical_formula_weight 134.21 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 7.0832(3) _cell_length_b 5.9177(3) _cell_length_c 21.2692(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 891.53(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3764 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.000 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.056 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Grown in-situ in a 0.30 mm glass capillary at 263.0 K. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 2187 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 30.06 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.980 _reflns_number_total 1273 _reflns_number_gt 1003 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.1037P] 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 1273 _refine_ls_number_parameters 74 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.182 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.028 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 1.07556(17) -0.09721(19) 0.69507(5) 0.0477(3) Uani 1 1 d . . . H1 H 1.119(2) -0.222(3) 0.7167(8) 0.075(4) Uiso 1 1 d . . . C2 C 1.01927(14) 0.06470(17) 0.66855(4) 0.0386(3) Uani 1 1 d . . . C3 C 0.95192(14) 0.26479(18) 0.63460(5) 0.0392(3) Uani 1 1 d . . . H3A H 0.9819(17) 0.411(2) 0.6601(6) 0.049(3) Uiso 1 1 d . . . H3B H 0.8119(19) 0.261(2) 0.6309(6) 0.053(3) Uiso 1 1 d . . . C4 C 1.03714(12) 0.28677(16) 0.56886(4) 0.0353(3) Uani 1 1 d . . . H4A H 1.1757(19) 0.3032(17) 0.5726(6) 0.047(3) Uiso 1 1 d . . . H4B H 1.0116(16) 0.1423(19) 0.5441(6) 0.047(3) Uiso 1 1 d . . . C5 C 0.95924(12) 0.48819(16) 0.53300(4) 0.0355(3) Uani 1 1 d . . . H5A H 0.9838(15) 0.6310(19) 0.5578(6) 0.043(3) Uiso 1 1 d . . . H5B H 0.8187(18) 0.4753(17) 0.5299(5) 0.043(3) 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 0.0612(7) 0.0422(6) 0.0397(5) 0.0022(4) 0.0044(4) 0.0013(5) C2 0.0442(5) 0.0400(5) 0.0317(4) -0.0040(4) 0.0035(3) -0.0032(4) C3 0.0445(6) 0.0399(5) 0.0333(4) -0.0020(4) 0.0019(3) 0.0040(4) C4 0.0365(5) 0.0380(5) 0.0313(4) -0.0020(4) 0.0001(3) 0.0025(3) C5 0.0354(5) 0.0393(5) 0.0318(4) -0.0027(4) -0.0005(3) 0.0025(3) _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 1.181(2) . ? C1 H1 0.92(2) . ? C2 C3 1.467(1) . ? C3 C4 1.529(1) . ? C3 H3A 1.04(1) . ? C3 H3B 1.00(1) . ? C4 C5 1.519(1) . ? C4 H4A 0.99(1) . ? C4 H4B 1.02(1) . ? C5 C5 1.524(2) 5_766 ? C5 H5A 1.01(1) . ? C5 H5B 1.00(1) . ? 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 H1 178.7(11) . . ? C1 C2 C3 178.87(11) . . ? C2 C3 C4 112.99(8) . . ? C2 C3 H3A 110.4(7) . . ? C4 C3 H3A 108.9(7) . . ? C2 C3 H3B 110.1(7) . . ? C4 C3 H3B 108.9(7) . . ? H3A C3 H3B 105.3(10) . . ? C5 C4 C3 112.50(7) . . ? C5 C4 H4A 108.9(6) . . ? C3 C4 H4A 109.0(7) . . ? C5 C4 H4B 109.5(7) . . ? C3 C4 H4B 109.3(7) . . ? H4A C4 H4B 107.5(9) . . ? C4 C5 C5 113.38(9) . 5_766 ? C4 C5 H5A 109.4(6) . . ? C5 C5 H5A 109.7(7) 5_766 . ? C4 C5 H5B 109.6(6) . . ? C5 C5 H5B 108.9(7) 5_766 . ? H5A C5 H5B 105.6(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 C3 C4 C5 177.24(8) . . . . ? C3 C4 C5 C5 -179.36(9) . . . 5_766 ? #===END