# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'P. Raithby' 'Al-Mahrooqi,Yaqoub' 'Al-Mandhary,Muna R.A.' 'Al-Suti,Mohammed K.' 'J. Attfield' 'A. Batsanov' 'J. C. Collings' 'Timothy C. Corcoran' 'William David' 'Neil Feeder' 'Richard Friend' 'Muhammad S. Khan' 'Anna Kohler' 'Todd Marder' 'Elisabeth A. Marseglia' 'K. P. Roscoe' 'Kenneth Shankland' 'L. M. Stimson' 'Chiu. C. Tang' 'Emilio Tedesco' _publ_contact_author_name 'Prof P Raithby' _publ_contact_author_address ; Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UK ; _publ_contact_author_email 'P.R.RAITHBY@BATH.AC.UK' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis and optical characterisation of platinum(II) poly-yne polymers incorporating substituted 1,4-diethynylbenzene derivatives and an investigation of the intermolecular interactions in the diethynylbenzene molecular precursors ; data_em9815 _database_code_CSD 196099 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound 2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 N' _chemical_formula_weight 141.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9188(17) _cell_length_b 12.030(4) _cell_length_c 11.026(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.17(2) _cell_angle_gamma 90.00 _cell_volume 761.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 15.7 _cell_measurement_theta_max 24.9 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.566 _exptl_absorpt_correction_type No _exptl_absorpt_correction_T_min 0.8137 _exptl_absorpt_correction_T_max 0.9199 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54120 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type STOE _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 90 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 1043 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.53 _diffrn_reflns_theta_max 54.97 _reflns_number_total 959 _reflns_number_gt 777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0736P)^2^+0.3480P] 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 0.010(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 959 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N1 N 0.5615(4) 0.47720(19) 0.3250(2) 0.0399(7) Uani 1 1 d . . . H1A H 0.4541 0.4584 0.3639 0.048 Uiso 1 1 calc R . . H1B H 0.6647 0.5286 0.3569 0.048 Uiso 1 1 calc R . . C1 C 0.0947(6) 0.1483(2) -0.0429(3) 0.0378(8) Uani 1 1 d . . . H1 H -0.0266 0.0972 -0.0769 0.045 Uiso 1 1 calc R . . C2 C 0.2387(5) 0.2090(2) -0.0025(2) 0.0331(7) Uani 1 1 d . . . C3 C 0.4178(4) 0.2906(2) 0.0522(2) 0.0293(7) Uani 1 1 d . . . C4 C 0.4060(4) 0.3444(2) 0.1618(2) 0.0313(7) Uani 1 1 d . . . H4 H 0.2863 0.3253 0.2018 0.038 Uiso 1 1 calc R . . C5 C 0.5682(4) 0.4262(2) 0.2142(2) 0.0294(7) Uani 1 1 d . . . C6 C 0.7459(4) 0.4526(2) 0.1538(2) 0.0296(7) Uani 1 1 d . . . C7 C 0.7563(4) 0.3963(2) 0.0451(2) 0.0339(8) Uani 1 1 d . . . H7 H 0.8774 0.4137 0.0054 0.041 Uiso 1 1 calc R . . C8 C 0.5956(5) 0.3161(2) -0.0063(3) 0.0338(7) Uani 1 1 d . . . H8 H 0.6055 0.2785 -0.0806 0.041 Uiso 1 1 calc R . . C9 C 0.9114(4) 0.5417(2) 0.2071(2) 0.0286(7) Uani 1 1 d . . . C10 C 1.0323(5) 0.6110(3) 0.2505(3) 0.0421(8) Uani 1 1 d . . . H10 H 1.1344 0.6694 0.2872 0.051 Uiso 1 1 calc R . . 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 N1 0.0335(13) 0.0503(15) 0.0377(14) -0.0131(12) 0.0124(11) -0.0072(11) C1 0.0439(18) 0.0367(18) 0.0306(16) 0.0002(13) 0.0048(14) 0.0003(15) C2 0.0384(17) 0.0319(16) 0.0304(16) 0.0064(13) 0.0109(13) 0.0088(15) C3 0.0301(15) 0.0260(15) 0.0299(15) 0.0038(12) 0.0034(12) 0.0015(12) C4 0.0273(15) 0.0340(16) 0.0325(15) 0.0043(13) 0.0072(12) 0.0003(12) C5 0.0247(14) 0.0309(15) 0.0309(15) 0.0026(12) 0.0036(11) 0.0037(12) C6 0.0261(14) 0.0304(15) 0.0308(15) 0.0049(12) 0.0038(11) 0.0025(12) C7 0.0296(15) 0.0376(17) 0.0361(17) 0.0030(13) 0.0115(12) -0.0008(13) C8 0.0369(16) 0.0340(16) 0.0312(15) -0.0002(13) 0.0097(12) 0.0003(13) C9 0.0244(14) 0.0327(16) 0.0294(15) 0.0079(13) 0.0081(12) 0.0036(14) C10 0.0402(18) 0.0426(18) 0.0449(18) 0.0043(16) 0.0130(14) 0.0028(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.376(3) . ? C1 C2 1.127(4) . ? C2 C3 1.462(4) . ? C3 C4 1.388(4) . ? C3 C8 1.396(4) . ? C4 C5 1.398(4) . ? C5 C6 1.412(4) . ? C6 C7 1.391(4) . ? C6 C9 1.474(4) . ? C7 C8 1.377(4) . ? C9 C10 1.126(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 C2 C3 177.4(3) . . ? C4 C3 C8 120.3(2) . . ? C4 C3 C2 119.1(2) . . ? C8 C3 C2 120.6(2) . . ? C3 C4 C5 120.8(2) . . ? N1 C5 C4 121.0(2) . . ? N1 C5 C6 120.3(2) . . ? C4 C5 C6 118.6(2) . . ? C7 C6 C5 119.5(2) . . ? C7 C6 C9 122.1(2) . . ? C5 C6 C9 118.3(2) . . ? C8 C7 C6 121.6(2) . . ? C7 C8 C3 119.1(3) . . ? C10 C9 C6 177.4(3) . . ? 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 31(6) . . . . ? C1 C2 C3 C8 -148(6) . . . . ? C8 C3 C4 C5 1.3(4) . . . . ? C2 C3 C4 C5 -177.3(2) . . . . ? C3 C4 C5 N1 -177.9(2) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? N1 C5 C6 C7 176.9(2) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? N1 C5 C6 C9 -4.7(4) . . . . ? C4 C5 C6 C9 177.9(2) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? C9 C6 C7 C8 -177.6(2) . . . . ? C6 C7 C8 C3 0.0(4) . . . . ? C4 C3 C8 C7 -1.0(4) . . . . ? C2 C3 C8 C7 177.5(2) . . . . ? C7 C6 C9 C10 164(6) . . . . ? C5 C6 C9 C10 -14(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 54.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045 #### data_em9816 _database_code_CSD 196100 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound 3 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 F' _chemical_formula_weight 144.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'F' 'F' 0.0727 0.0534 '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 3.8780(11) _cell_length_b 5.9470(12) _cell_length_c 15.800(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.46(3) _cell_angle_gamma 90.00 _cell_volume 363.72(17) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 24.76 _exptl_crystal_description Block _exptl_crystal_colour 'Light purple' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 148 _exptl_absorpt_coefficient_mu 0.770 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_T_max 0.572 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type STOE _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 920 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.61 _diffrn_reflns_theta_max 54.99 _reflns_number_total 460 _reflns_number_gt 369 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.1499P] 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 0.037(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 460 _refine_ls_number_parameters 56 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.4062(7) 0.0792(5) 0.17851(18) 0.0510(9) Uani 1 1 d . . . H1 H 0.5033 -0.0203 0.2206 0.061 Uiso 1 1 calc R . . C2 C 0.2856(6) 0.2027(4) 0.12629(15) 0.0405(8) Uani 1 1 d . A . C3 C 0.1403(6) 0.3519(4) 0.06209(15) 0.0380(8) Uani 1 1 d . . . C4 C -0.0039(6) 0.5573(4) 0.08345(15) 0.0410(8) Uani 0.50 1 d P A 1 F1 F -0.0063(8) 0.6036(5) 0.16056(17) 0.0550(10) Uani 0.50 1 d P A 1 C4' C -0.0039(6) 0.5573(4) 0.08345(15) 0.0410(8) Uani 0.50 1 d P A 2 H4' H -0.0071 0.5972 0.1416 0.049 Uiso 0.50 1 calc PR A 2 C5 C -0.1415(6) 0.7037(4) 0.02343(15) 0.0401(8) Uani 1 1 d . . 2 H5 H -0.2373 0.8426 0.0402 0.048 Uiso 1 1 calc R . 2 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 0.0621(18) 0.0412(17) 0.0484(18) 0.0027(14) -0.0077(13) 0.0013(14) C2 0.0395(15) 0.0371(16) 0.0445(17) 0.0005(14) -0.0010(12) -0.0042(12) C3 0.0350(14) 0.0336(15) 0.0452(17) 0.0060(13) 0.0009(11) -0.0069(12) C4 0.0444(16) 0.0397(16) 0.0390(16) 0.0017(13) 0.0045(11) -0.0046(12) F1 0.083(2) 0.0454(19) 0.0362(17) -0.0041(15) 0.0022(14) 0.0076(16) C4' 0.0444(16) 0.0397(16) 0.0390(16) 0.0017(13) 0.0045(11) -0.0046(12) C5 0.0414(15) 0.0322(17) 0.0469(16) 0.0008(13) 0.0036(11) -0.0030(12) _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 1.180(4) . ? C2 C3 1.437(3) . ? C3 C5 1.391(3) 3_565 ? C3 C4 1.393(4) . ? C4 F1 1.250(3) . ? C5 C3 1.391(3) 3_565 ? 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 C2 C3 179.4(3) . . ? C5 C3 C4 117.9(2) 3_565 . ? C5 C3 C2 121.0(2) 3_565 . ? C4 C3 C2 121.1(2) . . ? F1 C4 C3 117.1(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 54.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.166 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.038 #### data_em9818 _database_code_CSD 196101 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound 4 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H4 F2' _chemical_formula_weight 162.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'F' 'F' 0.0727 0.0534 '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 3.8535(7) _cell_length_b 5.9060(10) _cell_length_c 16.221(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.23(3) _cell_angle_gamma 90.00 _cell_volume 367.63(15) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 64 _cell_measurement_theta_min 15.34 _cell_measurement_theta_max 25.0 _exptl_crystal_description Block _exptl_crystal_colour 'Light purple' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 164 _exptl_absorpt_coefficient_mu 1.032 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.7204 _exptl_absorpt_correction_T_max 0.8605 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Stoe _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 0.7 _diffrn_reflns_number 510 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.48 _diffrn_reflns_theta_max 55.01 _reflns_number_total 466 _reflns_number_gt 431 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+0.1635P] 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 0.038(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 466 _refine_ls_number_parameters 56 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 F1 F -0.0079(3) 0.09857(17) 0.16258(6) 0.0378(5) Uani 1 1 d . . . C4 C -0.0038(4) 0.0500(3) 0.08132(10) 0.0241(5) Uani 1 1 d . . . C5 C -0.1474(4) 0.2013(3) 0.02434(10) 0.0250(5) Uani 1 1 d . . . H5 H -0.2462 0.3385 0.0420 0.030 Uiso 1 1 calc R . . C3 C 0.1483(4) -0.1532(3) 0.05992(10) 0.0227(5) Uani 1 1 d . . . C2 C 0.3026(4) -0.3040(3) 0.12243(11) 0.0270(5) Uani 1 1 d . . . C1 C 0.4325(5) -0.4273(3) 0.17360(11) 0.0338(6) Uani 1 1 d . . . H1 H 0.5370 -0.5265 0.2148 0.041 Uiso 1 1 calc R . . 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 F1 0.0584(8) 0.0295(7) 0.0256(7) -0.0033(5) 0.0042(5) 0.0059(5) C4 0.0293(10) 0.0217(10) 0.0213(10) -0.0027(8) 0.0029(7) -0.0047(8) C5 0.0281(10) 0.0157(10) 0.0314(10) -0.0026(8) 0.0042(7) -0.0001(8) C3 0.0224(9) 0.0165(10) 0.0291(10) 0.0011(8) 0.0011(7) -0.0043(7) C2 0.0288(10) 0.0207(10) 0.0314(11) -0.0032(9) 0.0024(8) -0.0027(8) C1 0.0428(11) 0.0257(11) 0.0318(11) 0.0021(9) -0.0020(9) 0.0045(9) _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 F1 C4 1.3504(19) . ? C4 C5 1.366(2) . ? C4 C3 1.394(2) . ? C5 C3 1.396(2) 3 ? C3 C5 1.396(2) 3 ? C3 C2 1.437(2) . ? C2 C1 1.181(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 F1 C4 C5 118.79(15) . . ? F1 C4 C3 117.94(14) . . ? C5 C4 C3 123.27(15) . . ? C4 C5 C3 119.62(15) . 3 ? C4 C3 C5 117.11(15) . 3 ? C4 C3 C2 120.95(15) . . ? C5 C3 C2 121.94(15) 3 . ? C1 C2 C3 179.35(19) . . ? 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 F1 C4 C5 C3 -179.44(14) . . . 3 ? C3 C4 C5 C3 0.6(3) . . . 3 ? F1 C4 C3 C5 179.46(14) . . . 3 ? C5 C4 C3 C5 -0.6(3) . . . 3 ? F1 C4 C3 C2 -1.3(2) . . . . ? C5 C4 C3 C2 178.61(15) . . . . ? C4 C3 C2 C1 -108(17) . . . . ? C5 C3 C2 C1 71(17) 3 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 55.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.148 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.031 #### data_em9901 _database_code_CSD 196102 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound 5 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H2 F4' _chemical_formula_weight 198.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'F' 'F' 0.0727 0.0534 '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+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 5.7642(9) _cell_length_b 11.4632(18) _cell_length_c 6.1120(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.27(2) _cell_angle_gamma 90.00 _cell_volume 398.58(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 58 _cell_measurement_theta_min 15.32 _cell_measurement_theta_max 24.11 _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 1.451 _exptl_absorpt_correction_type No _exptl_absorpt_correction_T_min 0.6700 _exptl_absorpt_correction_T_max 0.8117 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Stoe _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 510 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 7.34 _diffrn_reflns_theta_max 54.99 _reflns_number_total 506 _reflns_number_gt 333 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.0815P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 506 _refine_ls_number_parameters 64 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 F1 F 0.2290(3) 0.19450(16) 0.6648(3) 0.0437(6) Uani 1 1 d . . . F2 F -0.0981(3) 0.10088(15) 0.8759(3) 0.0391(6) Uani 1 1 d . . . C1 C -0.1722(5) -0.0501(3) 0.6112(5) 0.0284(7) Uani 1 1 d . . . C2 C -0.0508(5) 0.0503(3) 0.6896(5) 0.0291(8) Uani 1 1 d . . . C3 C 0.1161(5) 0.0978(3) 0.5815(5) 0.0304(8) Uani 1 1 d . . . C4 C -0.3493(6) -0.1006(3) 0.7238(5) 0.0340(8) Uani 1 1 d . . . C5 C -0.4911(6) -0.1404(3) 0.8191(6) 0.0459(10) Uani 1 1 d . . . H5 H -0.6062 -0.1728 0.8965 0.055 Uiso 1 1 calc R . . 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 F1 0.0541(12) 0.0340(10) 0.0430(11) -0.0073(10) 0.0079(9) -0.0116(10) F2 0.0512(12) 0.0330(11) 0.0351(10) -0.0027(9) 0.0131(8) 0.0055(9) C1 0.0282(16) 0.0272(17) 0.0295(18) 0.0063(15) 0.0042(14) 0.0043(15) C2 0.0339(18) 0.0252(18) 0.0287(18) -0.0013(15) 0.0069(14) 0.0044(17) C3 0.0329(18) 0.0218(19) 0.0351(19) -0.0021(16) 0.0012(15) -0.0026(15) C4 0.0337(19) 0.0322(19) 0.0366(18) 0.0006(16) 0.0075(16) 0.0081(17) C5 0.038(2) 0.047(2) 0.057(2) 0.0044(19) 0.021(2) -0.0006(18) _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 F1 C3 1.343(3) . ? F2 C2 1.345(3) . ? C1 C3 1.384(4) 3_556 ? C1 C2 1.391(4) . ? C1 C4 1.441(5) . ? C2 C3 1.365(4) . ? C3 C1 1.384(4) 3_556 ? C4 C5 1.170(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 C3 C1 C2 116.5(3) 3_556 . ? C3 C1 C4 121.9(3) 3_556 . ? C2 C1 C4 121.6(3) . . ? F2 C2 C3 119.5(3) . . ? F2 C2 C1 119.3(3) . . ? C3 C2 C1 121.2(3) . . ? F1 C3 C2 118.8(3) . . ? F1 C3 C1 118.9(3) . 3_556 ? C2 C3 C1 122.2(3) . 3_556 ? C5 C4 C1 178.6(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 54.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.178 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.046 ####END