Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_s92 _database_code_CSD 170065 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Bruce, Duncan W.' 'Gelbrich, Thomas' 'Hursthouse, Michael B.' 'Luckhurst, G. R.' 'Omnes, Laurent' 'Timimi, B.' _publ_contact_author_name 'Prof Duncan W. Bruce' _publ_contact_author_address ; School of Chemistry University of Exeter Stocker Road EXETER EX4 4QD UNITED KINGDOM ; _publ_contact_author_email 'D.BRUCE@EX.AC.UK' _publ_section_title ; Specific molecular interactions in Pd(II) complexes identify a new approach to the biaxial nematic phase ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 F3 N O4 Pd' _chemical_formula_weight 499.75 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' 'N' 'N' 0.0061 0.0033 '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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Pd' 'Pd' -0.9988 1.0072 '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 12.8622(12) _cell_length_b 17.3734(18) _cell_length_c 8.6466(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.13(3) _cell_angle_gamma 90.00 _cell_volume 1924.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9321 _exptl_absorpt_correction_T_max 0.9508 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7543 _diffrn_reflns_av_R_equivalents 0.1112 _diffrn_reflns_av_sigmaI/netI 0.1070 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 24.00 _reflns_number_total 2857 _reflns_number_gt 1705 _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^)+(0.0000P)^2^+30.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2857 _refine_ls_number_parameters 202 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1900 _refine_ls_R_factor_gt 0.1235 _refine_ls_wR_factor_ref 0.2482 _refine_ls_wR_factor_gt 0.2278 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.004 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 Pd1 Pd 0.03989(12) 0.07959(6) 0.39643(15) 0.0731(6) Uani 1 1 d . . . N1 N 0.0636(13) 0.1653(6) 0.5617(15) 0.065(4) Uani 1 1 d . . . O1 O 0.1970(11) 0.0429(7) 0.4125(14) 0.089(4) Uani 1 1 d . . . O2 O -0.0041(10) -0.0010(5) 0.2333(12) 0.078(4) Uani 1 1 d . . . O3 O -0.3693(16) 0.1383(12) 0.186(2) 0.160(7) Uiso 1 1 d D . . O4 O 0.4236(14) 0.2176(12) 0.958(2) 0.166(8) Uani 1 1 d D . . C1 C -0.0998(15) 0.1216(9) 0.373(2) 0.065(5) Uani 1 1 d . . . C2 C -0.1878(19) 0.1039(9) 0.275(3) 0.098(7) Uani 1 1 d . . . H2 H -0.1872 0.0610 0.2070 0.117 Uiso 1 1 calc R . . C3 C -0.2767(19) 0.1490(16) 0.277(3) 0.104(7) Uiso 1 1 d D . . C4 C -0.2819(19) 0.2109(14) 0.373(3) 0.106(8) Uani 1 1 d . . . H4 H -0.3440 0.2406 0.3688 0.128 Uiso 1 1 calc R . . C5 C -0.2016(16) 0.2299(14) 0.470(2) 0.089(6) Uani 1 1 d . . . H5 H -0.2077 0.2726 0.5373 0.107 Uiso 1 1 calc R . . C6 C -0.1068(15) 0.1887(8) 0.478(2) 0.069(5) Uani 1 1 d . . . C7 C -0.3676(19) 0.0824(13) 0.094(2) 0.118(8) Uani 1 1 d D . . H7A H -0.4346 0.0790 0.0313 0.177 Uiso 1 1 calc R . . H7B H -0.3554 0.0348 0.1540 0.177 Uiso 1 1 calc R . . H7C H -0.3114 0.0897 0.0264 0.177 Uiso 1 1 calc R . . C8 C -0.0190(13) 0.2066(9) 0.5775(19) 0.059(4) Uiso 1 1 d . . . H8 H -0.0194 0.2466 0.6523 0.071 Uiso 1 1 calc R . . C9 C 0.1535(19) 0.1807(10) 0.659(2) 0.086(6) Uani 1 1 d . . . C10 C 0.1872(19) 0.2581(11) 0.697(2) 0.095(7) Uani 1 1 d . . . H10 H 0.1493 0.3011 0.6543 0.114 Uiso 1 1 calc R . . C11 C 0.2784(19) 0.2686(13) 0.801(3) 0.104(8) Uani 1 1 d . . . H11 H 0.3006 0.3194 0.8268 0.125 Uiso 1 1 calc R . . C12 C 0.333(2) 0.210(2) 0.862(3) 0.132(10) Uiso 1 1 d D . . C13 C 0.299(2) 0.1344(15) 0.812(4) 0.129(9) Uani 1 1 d . . . H13 H 0.3397 0.0915 0.8482 0.154 Uiso 1 1 calc R . . C14 C 0.2139(19) 0.1215(12) 0.721(3) 0.097(7) Uani 1 1 d . . . H14 H 0.1939 0.0700 0.6964 0.117 Uiso 1 1 calc R . . C15 C 0.452(2) 0.2828(14) 1.009(3) 0.136(9) Uiso 1 1 d D . . H15A H 0.5153 0.2773 1.0808 0.203 Uiso 1 1 calc R . . H15B H 0.3966 0.3059 1.0639 0.203 Uiso 1 1 calc R . . H15C H 0.4674 0.3160 0.9222 0.203 Uiso 1 1 calc R . . C16 C 0.2173(13) -0.0236(13) 0.313(3) 0.102(8) Uani 1 1 d D . . C17 C 0.1495(13) -0.0594(9) 0.2241(17) 0.058(4) Uiso 1 1 d D . . H17 H 0.1787 -0.1023 0.1754 0.069 Uiso 1 1 calc R . . C18 C 0.0530(13) -0.0523(10) 0.184(2) 0.068(4) Uiso 1 1 d D . . C19 C 0.0040(17) -0.1066(13) 0.062(2) 0.108(7) Uiso 1 1 d . . . H19A H -0.0711 -0.0963 0.0456 0.162 Uiso 1 1 calc R . . H19B H 0.0153 -0.1598 0.0970 0.162 Uiso 1 1 calc R . . H19C H 0.0360 -0.0988 -0.0353 0.162 Uiso 1 1 calc R . . C20 C 0.332(2) -0.0273(7) 0.355(3) 0.120(8) Uiso 1 1 d D . . F1 F 0.3711(12) -0.0969(8) 0.3043(15) 0.157(6) Uiso 1 1 d D . . F2 F 0.3903(11) 0.0228(8) 0.2705(15) 0.148(5) Uiso 1 1 d D . . F3 F 0.3806(11) -0.0213(7) 0.4971(15) 0.140(5) Uiso 1 1 d 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 Pd1 0.1414(14) 0.0192(5) 0.0643(8) 0.0017(6) 0.0401(8) 0.0067(7) N1 0.112(13) 0.033(6) 0.051(8) 0.012(6) 0.018(8) 0.003(7) O1 0.135(12) 0.052(6) 0.086(9) 0.012(6) 0.053(8) 0.007(7) O2 0.157(11) 0.017(4) 0.065(7) -0.005(4) 0.042(7) -0.002(5) O4 0.114(14) 0.20(2) 0.189(19) -0.082(16) 0.010(13) -0.067(13) C1 0.080(14) 0.048(9) 0.070(12) 0.013(8) 0.032(10) -0.009(9) C2 0.15(2) 0.039(9) 0.113(17) 0.026(10) 0.046(16) -0.028(11) C4 0.094(18) 0.122(19) 0.113(18) 0.060(16) 0.062(15) 0.039(14) C5 0.065(14) 0.121(17) 0.079(14) 0.017(13) -0.012(11) 0.010(13) C6 0.090(14) 0.034(7) 0.088(13) 0.019(8) 0.034(11) 0.020(8) C7 0.19(2) 0.097(15) 0.072(14) -0.025(12) 0.062(14) -0.014(16) C9 0.128(19) 0.049(10) 0.085(14) -0.011(10) 0.039(13) -0.023(11) C10 0.14(2) 0.067(11) 0.081(14) 0.002(10) 0.052(14) -0.017(12) C11 0.105(18) 0.104(17) 0.112(18) -0.055(15) 0.055(15) -0.053(15) C13 0.12(2) 0.094(17) 0.18(3) -0.025(18) 0.03(2) -0.015(15) C14 0.099(18) 0.062(12) 0.13(2) 0.013(12) -0.002(15) -0.017(12) C16 0.037(12) 0.14(2) 0.128(19) 0.092(17) 0.012(11) 0.010(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 Pd1 C1 1.933(18) . ? Pd1 O2 2.032(10) . ? Pd1 N1 2.068(13) . ? Pd1 O1 2.111(13) . ? N1 C8 1.299(18) . ? N1 C9 1.39(2) . ? O1 C16 1.48(3) . ? O2 C18 1.253(18) . ? O3 C7 1.254(19) . ? O3 C3 1.38(2) . ? O4 C15 1.259(19) . ? O4 C12 1.38(2) . ? C1 C2 1.39(3) . ? C1 C6 1.48(2) . ? C2 C3 1.39(3) . ? C2 H2 0.9500 . ? C3 C4 1.36(3) . ? C4 C5 1.32(3) . ? C4 H4 0.9500 . ? C5 C6 1.41(2) . ? C5 H5 0.9500 . ? C6 C8 1.39(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8 0.9500 . ? C9 C14 1.37(3) . ? C9 C10 1.44(2) . ? C10 C11 1.42(3) . ? C10 H10 0.9500 . ? C11 C12 1.32(3) . ? C11 H11 0.9500 . ? C12 C13 1.44(4) . ? C13 C14 1.31(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.273(16) . ? C16 C20 1.49(3) . ? C17 C18 1.263(16) . ? C17 H17 0.9500 . ? C18 C19 1.51(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 F3 1.33(3) . ? C20 F1 1.395(17) . ? C20 F2 1.395(17) . ? 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 Pd1 O2 89.4(7) . . ? C1 Pd1 N1 82.9(7) . . ? O2 Pd1 N1 172.3(6) . . ? C1 Pd1 O1 174.9(5) . . ? O2 Pd1 O1 92.5(5) . . ? N1 Pd1 O1 95.2(6) . . ? C8 N1 C9 118.3(15) . . ? C8 N1 Pd1 113.5(13) . . ? C9 N1 Pd1 128.1(11) . . ? C16 O1 Pd1 114.6(11) . . ? C18 O2 Pd1 126.1(12) . . ? C7 O3 C3 114(2) . . ? C15 O4 C12 120(3) . . ? C2 C1 C6 117.2(17) . . ? C2 C1 Pd1 132.7(15) . . ? C6 C1 Pd1 109.9(14) . . ? C1 C2 C3 120(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 O3 112(3) . . ? C4 C3 C2 122(2) . . ? O3 C3 C2 126(3) . . ? C5 C4 C3 121(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 122(2) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C8 C6 C5 124.6(17) . . ? C8 C6 C1 117.5(15) . . ? C5 C6 C1 117.9(19) . . ? O3 C7 H7A 109.5 . . ? O3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C6 116.0(16) . . ? N1 C8 H8 122.0 . . ? C6 C8 H8 122.0 . . ? C14 C9 N1 120.2(17) . . ? C14 C9 C10 117(2) . . ? N1 C9 C10 122(2) . . ? C11 C10 C9 119(2) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C12 C11 C10 122(2) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 O4 124(3) . . ? C11 C12 C13 117(2) . . ? O4 C12 C13 119(3) . . ? C14 C13 C12 124(3) . . ? C14 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C13 C14 C9 121(2) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 O1 125.9(17) . . ? C17 C16 C20 138(2) . . ? O1 C16 C20 96.5(17) . . ? C18 C17 C16 136.1(19) . . ? C18 C17 H17 111.9 . . ? C16 C17 H17 112.0 . . ? O2 C18 C17 124.7(17) . . ? O2 C18 C19 117.4(16) . . ? C17 C18 C19 117.9(17) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? F3 C20 F1 102.1(16) . . ? F3 C20 F2 102.0(16) . . ? F1 C20 F2 98.6(17) . . ? F3 C20 C16 126(2) . . ? F1 C20 C16 109.5(19) . . ? F2 C20 C16 114.2(18) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 1.617 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.157