data_global _journal_coden_Cambridge 1145 _publ_requested_journal J.Mater.Chem. _publ_contact_author_name 'Dr Paul James Low' _publ_contact_author_address ; Department of Chemistry University of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_letter ; The CIF file contains data for the structure 4 from the paper "The molecular structures and electrochemical response of "twisted" tetra(aryl)benzidenes" by P.J.Low, M.A.J.Paterson, A.Goeta, D.S.Yufit, J.A.K.Howard, J.Cherryman, D.Tackley, B.Brown The paper will be submitted to Journal of Materials Chemistry ; loop_ _publ_author_name _publ_author_address 'Low, Paul J.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Paterson, Michael A.J.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Goeta, Andres' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Yufit, D.S.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Howard, Judith A.K.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Cherryman, Julian' ; Avecia Ltd. PO Box 42 Hexagon House, Blackley Manchester M9 8ZS UK ; 'Tackley, Daniel' ; Avecia Ltd. PO Box 42 Hexagon House, Blackley Manchester M9 8ZS UK ; 'Brown, Bev' ; Avecia Ltd. PO Box 42 Hexagon House, Blackley Manchester M9 8ZS UK ; _publ_section_title ; The molecular structures and electrochemical response of "twisted" tetra(aryl) benzidenes ; data_s068 _database_code_depnum_ccdc_archive 'CCDC 235057' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetra(4-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine ; _chemical_name_common ? _chemical_melting_point 203-205 _chemical_formula_moiety 'C40 H36 N2, C H2 Cl2' _chemical_formula_sum 'C41 H38 Cl2 N2' _chemical_formula_weight 629.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5659(3) _cell_length_b 13.6399(2) _cell_length_c 14.6862(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.78(1) _cell_angle_gamma 90.00 _cell_volume 3320.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7075 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.50 _exptl_crystal_description 'shapeless lump' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 6K' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16149 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 29.49 _reflns_number_total 4596 _reflns_number_gt 3703 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0600P)^2^+1.8000P] 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 4596 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.26024(6) 0.48846(7) 0.06632(7) 0.0182(2) Uani 1 1 d . . . C1 C 0.03869(7) 0.46391(8) -0.20283(8) 0.0172(2) Uani 1 1 d . . . C2 C 0.11198(7) 0.44139(9) -0.20329(9) 0.0197(2) Uani 1 1 d . . . C3 C 0.18507(7) 0.44803(9) -0.11548(9) 0.0191(2) Uani 1 1 d . . . C4 C 0.18706(7) 0.47756(8) -0.02332(8) 0.0169(2) Uani 1 1 d . . . C5 C 0.11381(7) 0.49717(8) -0.02115(9) 0.0184(2) Uani 1 1 d . . . C6 C 0.04151(7) 0.49093(8) -0.10900(9) 0.0183(2) Uani 1 1 d . . . C7 C 0.27167(7) 0.57174(8) 0.13012(8) 0.0174(2) Uani 1 1 d . . . C8 C 0.31718(7) 0.56198(9) 0.23531(9) 0.0202(2) Uani 1 1 d . . . C9 C 0.33408(7) 0.64374(9) 0.29861(9) 0.0220(2) Uani 1 1 d . . . C10 C 0.30573(7) 0.73647(9) 0.25867(10) 0.0220(2) Uani 1 1 d . . . C11 C 0.25772(8) 0.74431(9) 0.15361(10) 0.0237(2) Uani 1 1 d . . . C12 C 0.24080(7) 0.66363(9) 0.08962(9) 0.0214(2) Uani 1 1 d . . . C13 C 0.32807(10) 0.82604(11) 0.32562(12) 0.0316(3) Uani 1 1 d . . . C14 C 0.33159(7) 0.44063(8) 0.07518(8) 0.0175(2) Uani 1 1 d . . . C15 C 0.33794(8) 0.33890(9) 0.08190(9) 0.0224(2) Uani 1 1 d . . . C16 C 0.40869(8) 0.29334(9) 0.09413(10) 0.0257(3) Uani 1 1 d . . . C17 C 0.47464(8) 0.34723(10) 0.10101(9) 0.0252(3) Uani 1 1 d . . . C18 C 0.46693(8) 0.44885(10) 0.09264(10) 0.0258(3) Uani 1 1 d . . . C19 C 0.39630(7) 0.49522(9) 0.07908(9) 0.0219(2) Uani 1 1 d . . . C20 C 0.55247(10) 0.29757(14) 0.11870(13) 0.0395(4) Uani 1 1 d . . . Cl1 Cl 0.46247(3) 0.76033(3) 0.13896(4) 0.05839(17) Uani 1 1 d . . . C1S C 0.5000 0.68881(14) 0.2500 0.0316(4) Uani 1 2 d S . . H2 H 0.1123(9) 0.4221(12) -0.2667(12) 0.025(4) Uiso 1 1 d . . . H3 H 0.2337(9) 0.4357(11) -0.1178(11) 0.017(3) Uiso 1 1 d . . . H5 H 0.1145(10) 0.5179(12) 0.0427(13) 0.027(4) Uiso 1 1 d . . . H6 H -0.0072(10) 0.5072(11) -0.1063(12) 0.021(4) Uiso 1 1 d . . . H8 H 0.3366(10) 0.4966(12) 0.2620(13) 0.028(4) Uiso 1 1 d . . . H9 H 0.3653(10) 0.6352(12) 0.3691(13) 0.032(4) Uiso 1 1 d . . . H11 H 0.2377(10) 0.8089(12) 0.1242(12) 0.027(4) Uiso 1 1 d . . . H12 H 0.2096(9) 0.6719(11) 0.0174(12) 0.025(4) Uiso 1 1 d . . . H131 H 0.3490(15) 0.8098(19) 0.395(2) 0.074(7) Uiso 1 1 d . . . H132 H 0.3613(15) 0.8699(17) 0.3100(19) 0.070(7) Uiso 1 1 d . . . H133 H 0.2821(15) 0.8667(18) 0.3156(19) 0.074(7) Uiso 1 1 d . . . H15 H 0.2934(10) 0.3008(12) 0.0795(13) 0.030(4) Uiso 1 1 d . . . H16 H 0.4117(11) 0.2198(14) 0.0961(14) 0.040(5) Uiso 1 1 d . . . H18 H 0.5090(12) 0.4874(13) 0.0946(14) 0.038(5) Uiso 1 1 d . . . H19 H 0.3902(10) 0.5672(13) 0.0719(13) 0.031(4) Uiso 1 1 d . . . H201 H 0.5443(15) 0.2302(19) 0.0941(19) 0.070(7) Uiso 1 1 d . . . H202 H 0.5808(15) 0.3313(19) 0.0873(19) 0.076(7) Uiso 1 1 d . . . H203 H 0.5896(16) 0.284(2) 0.191(2) 0.083(8) Uiso 1 1 d . . . H1S H 0.4558(11) 0.6505(15) 0.2475(15) 0.048(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 N1 0.0137(4) 0.0196(4) 0.0167(4) -0.0029(3) 0.0028(4) 0.0008(3) C1 0.0157(5) 0.0164(5) 0.0162(5) 0.0007(4) 0.0043(4) -0.0006(4) C2 0.0181(5) 0.0233(5) 0.0160(5) -0.0022(4) 0.0063(4) -0.0005(4) C3 0.0153(5) 0.0225(5) 0.0189(5) -0.0007(4) 0.0071(4) 0.0004(4) C4 0.0146(5) 0.0168(5) 0.0161(5) 0.0009(4) 0.0040(4) -0.0004(4) C5 0.0174(5) 0.0209(5) 0.0160(5) -0.0005(4) 0.0070(4) -0.0003(4) C6 0.0153(5) 0.0203(5) 0.0184(5) 0.0005(4) 0.0069(4) 0.0008(4) C7 0.0148(5) 0.0189(5) 0.0175(5) -0.0021(4) 0.0065(4) -0.0019(4) C8 0.0189(5) 0.0208(5) 0.0185(5) 0.0008(4) 0.0062(4) -0.0002(4) C9 0.0209(6) 0.0278(6) 0.0165(5) -0.0028(4) 0.0079(5) -0.0026(5) C10 0.0207(6) 0.0239(5) 0.0246(6) -0.0059(4) 0.0131(5) -0.0020(4) C11 0.0248(6) 0.0194(5) 0.0267(6) -0.0001(4) 0.0113(5) 0.0024(4) C12 0.0216(6) 0.0218(5) 0.0184(5) 0.0007(4) 0.0067(5) 0.0011(4) C13 0.0358(8) 0.0281(6) 0.0329(7) -0.0122(5) 0.0172(6) -0.0024(6) C14 0.0157(5) 0.0191(5) 0.0145(5) -0.0003(4) 0.0041(4) 0.0006(4) C15 0.0226(6) 0.0204(5) 0.0237(6) 0.0014(4) 0.0099(5) 0.0000(4) C16 0.0297(6) 0.0216(6) 0.0246(6) 0.0032(5) 0.0112(5) 0.0065(5) C17 0.0208(6) 0.0348(7) 0.0176(5) 0.0003(5) 0.0065(5) 0.0081(5) C18 0.0186(6) 0.0331(6) 0.0248(6) -0.0043(5) 0.0090(5) -0.0040(5) C19 0.0204(6) 0.0214(5) 0.0222(5) -0.0019(4) 0.0082(5) -0.0025(4) C20 0.0278(7) 0.0534(10) 0.0356(8) 0.0018(7) 0.0128(6) 0.0173(7) Cl1 0.0417(2) 0.0453(2) 0.0665(3) 0.0272(2) 0.0053(2) -0.00461(18) C1S 0.0362(11) 0.0221(8) 0.0438(11) 0.000 0.0244(10) 0.000 _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 C4 1.4104(14) . y N1 C7 1.4263(14) . y N1 C14 1.4290(14) . y C1 C2 1.3979(15) . y C1 C6 1.4045(15) . y C1 C1 1.480(2) 2_554 y C2 C3 1.3912(16) . y C2 H2 0.971(15) . ? C3 C4 1.3966(15) . y C3 H3 0.934(14) . ? C4 C5 1.4005(15) . y C5 C6 1.3831(16) . y C5 H5 0.974(16) . ? C6 H6 0.949(16) . ? C7 C8 1.3935(16) . y C7 C12 1.3950(16) . y C8 C9 1.3940(16) . y C8 H8 0.975(16) . ? C9 C10 1.3939(17) . y C9 H9 0.939(17) . ? C10 C11 1.3955(18) . y C10 C13 1.5045(17) . y C11 C12 1.3880(17) . y C11 H11 0.979(17) . ? C12 H12 0.959(16) . ? C13 H131 0.93(3) . ? C13 H132 0.96(2) . ? C13 H133 0.97(3) . ? C14 C15 1.3924(16) . y C14 C19 1.3925(16) . y C15 C16 1.3897(17) . y C15 H15 0.964(17) . ? C16 C17 1.3922(19) . y C16 H16 1.005(19) . ? C17 C18 1.3932(19) . y C17 C20 1.5085(18) . y C18 C19 1.3871(17) . y C18 H18 0.931(19) . ? C19 H19 0.988(18) . y C20 H201 0.97(3) . ? C20 H202 0.96(3) . ? C20 H203 0.99(3) . ? Cl1 C1S 1.7528(11) . y C1S Cl1 1.7528(11) 2_655 ? C1S H1S 0.960(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C7 119.52(9) . . y C4 N1 C14 120.03(9) . . y C7 N1 C14 116.51(9) . . y C2 C1 C6 117.15(10) . . y C2 C1 C1 122.14(12) . 2_554 y C6 C1 C1 120.65(12) . 2_554 y C3 C2 C1 121.76(10) . . y C3 C2 H2 118.8(9) . . ? C1 C2 H2 119.4(9) . . ? C2 C3 C4 120.39(10) . . y C2 C3 H3 120.7(9) . . ? C4 C3 H3 118.9(9) . . ? C3 C4 C5 118.37(10) . . y C3 C4 N1 121.92(10) . . y C5 C4 N1 119.71(10) . . y C6 C5 C4 120.75(10) . . y C6 C5 H5 120.1(10) . . ? C4 C5 H5 119.1(10) . . ? C5 C6 C1 121.52(10) . . y C5 C6 H6 119.3(9) . . ? C1 C6 H6 119.2(9) . . ? C8 C7 C12 119.07(10) . . y C8 C7 N1 119.25(10) . . y C12 C7 N1 121.63(10) . . y C7 C8 C9 120.31(11) . . y C7 C8 H8 117.6(10) . . ? C9 C8 H8 122.1(10) . . ? C8 C9 C10 121.10(11) . . y C8 C9 H9 118.6(10) . . ? C10 C9 H9 120.3(10) . . ? C9 C10 C11 117.82(11) . . y C9 C10 C13 121.42(12) . . y C11 C10 C13 120.74(12) . . y C12 C11 C10 121.66(11) . . y C12 C11 H11 119.3(9) . . ? C10 C11 H11 118.9(9) . . ? C11 C12 C7 119.96(11) . . y C11 C12 H12 119.7(9) . . ? C7 C12 H12 120.3(9) . . ? C10 C13 H131 112.0(16) . . ? C10 C13 H132 111.5(14) . . ? H131 C13 H132 114(2) . . ? C10 C13 H133 113.6(15) . . ? H131 C13 H133 102(2) . . ? H132 C13 H133 102.9(19) . . ? C15 C14 C19 119.09(11) . . y C15 C14 N1 120.45(10) . . y C19 C14 N1 120.45(10) . . y C16 C15 C14 119.97(11) . . y C16 C15 H15 120.6(10) . . ? C14 C15 H15 119.4(10) . . ? C15 C16 C17 121.50(11) . . y C15 C16 H16 119.2(11) . . ? C17 C16 H16 119.3(11) . . ? C16 C17 C18 117.83(11) . . y C16 C17 C20 121.21(13) . . y C18 C17 C20 120.95(13) . . y C19 C18 C17 121.28(12) . . y C19 C18 H18 118.2(11) . . ? C17 C18 H18 120.5(11) . . ? C18 C19 C14 120.29(11) . . y C18 C19 H19 121.6(10) . . ? C14 C19 H19 118.1(10) . . ? C17 C20 H201 112.5(14) . . ? C17 C20 H202 113.1(15) . . ? H201 C20 H202 108(2) . . ? C17 C20 H203 114.8(15) . . ? H201 C20 H203 98(2) . . ? H202 C20 H203 110(2) . . ? Cl1 C1S Cl1 112.37(11) 2_655 . y Cl1 C1S H1S 108.2(12) 2_655 . ? Cl1 C1S H1S 107.1(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.82(17) . . . . ? C1 C1 C2 C3 175.55(8) 2_554 . . . ? C1 C2 C3 C4 0.16(18) . . . . ? C2 C3 C4 C5 1.94(17) . . . . ? C2 C3 C4 N1 -177.71(10) . . . . ? C7 N1 C4 C3 136.64(11) . . . . ? C14 N1 C4 C3 -20.27(16) . . . . ? C7 N1 C4 C5 -43.00(15) . . . . ? C14 N1 C4 C5 160.09(10) . . . . ? C3 C4 C5 C6 -2.36(17) . . . . ? N1 C4 C5 C6 177.30(10) . . . . ? C4 C5 C6 C1 0.68(17) . . . . ? C2 C1 C6 C5 1.40(16) . . . . ? C1 C1 C6 C5 -176.01(8) 2_554 . . . ? C4 N1 C7 C8 146.32(11) . . . . ? C14 N1 C7 C8 -55.98(14) . . . . ? C4 N1 C7 C12 -35.96(15) . . . . ? C14 N1 C7 C12 121.74(12) . . . . ? C12 C7 C8 C9 -2.42(17) . . . . ? N1 C7 C8 C9 175.37(10) . . . . ? C7 C8 C9 C10 0.38(18) . . . . ? C8 C9 C10 C11 1.99(18) . . . . ? C8 C9 C10 C13 -176.05(11) . . . . ? C9 C10 C11 C12 -2.38(18) . . . . ? C13 C10 C11 C12 175.68(12) . . . . ? C10 C11 C12 C7 0.38(19) . . . . ? C8 C7 C12 C11 2.04(17) . . . . ? N1 C7 C12 C11 -175.69(11) . . . . ? C4 N1 C14 C15 -68.18(14) . . . . ? C7 N1 C14 C15 134.24(11) . . . . ? C4 N1 C14 C19 112.99(12) . . . . ? C7 N1 C14 C19 -44.59(14) . . . . ? C19 C14 C15 C16 1.12(18) . . . . ? N1 C14 C15 C16 -177.72(11) . . . . ? C14 C15 C16 C17 0.68(19) . . . . ? C15 C16 C17 C18 -1.60(19) . . . . ? C15 C16 C17 C20 177.41(12) . . . . ? C16 C17 C18 C19 0.75(19) . . . . ? C20 C17 C18 C19 -178.27(12) . . . . ? C17 C18 C19 C14 1.04(19) . . . . ? C15 C14 C19 C18 -1.97(18) . . . . ? N1 C14 C19 C18 176.87(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.539 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.053 #===END data_02srv096 _database_code_depnum_ccdc_archive 'CCDC 235058' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-Tetraphenyl-2,2',6,6'-tetramethyl-1,1'-biphenyl-4,4'-diamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 N2' _chemical_formula_sum 'C40 H36 N2' _chemical_formula_weight 544.71 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.7412(8) _cell_length_b 16.6699(12) _cell_length_c 18.7844(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.068(4) _cell_angle_gamma 90.00 _cell_volume 3027.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 980 _cell_measurement_theta_min 6.88 _cell_measurement_theta_max 21.48 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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-6000 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20949 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 30.51 _reflns_number_total 4619 _reflns_number_gt 3278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0340P)^2^+2.6309P] 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 4619 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.50454(14) 0.24844(7) 0.51497(6) 0.0299(3) Uani 1 1 d . . . C1 C 0.50233(14) 0.23241(8) 0.29005(6) 0.0240(3) Uani 1 1 d . . . C2 C 0.41065(14) 0.18528(8) 0.32430(7) 0.0251(3) Uani 1 1 d . . . C3 C 0.41256(14) 0.19037(8) 0.39867(7) 0.0260(3) Uani 1 1 d . . . C4 C 0.50486(15) 0.24095(8) 0.43928(7) 0.0266(3) Uani 1 1 d . . . C5 C 0.59670(15) 0.28671(8) 0.40519(7) 0.0277(3) Uani 1 1 d . . . C6 C 0.59546(14) 0.28363(8) 0.33092(7) 0.0261(3) Uani 1 1 d . . . C7 C 0.49505(14) 0.17941(8) 0.55755(7) 0.0255(3) Uani 1 1 d . . . C8 C 0.42143(16) 0.18008(9) 0.61701(8) 0.0328(3) Uani 1 1 d . . . C9 C 0.41321(17) 0.11084(10) 0.65744(8) 0.0371(3) Uani 1 1 d . . . C10 C 0.47614(17) 0.04039(9) 0.63959(8) 0.0347(3) Uani 1 1 d . . . C11 C 0.54895(15) 0.03986(8) 0.58123(8) 0.0298(3) Uani 1 1 d . . . C12 C 0.55943(15) 0.10842(8) 0.54038(7) 0.0271(3) Uani 1 1 d . . . C13 C 0.30581(16) 0.13177(9) 0.28215(8) 0.0313(3) Uani 1 1 d . . . C14 C 0.48585(15) 0.32637(8) 0.54325(7) 0.0286(3) Uani 1 1 d . . . C15 C 0.39198(15) 0.37948(9) 0.50696(8) 0.0318(3) Uani 1 1 d . . . C16 C 0.37406(17) 0.45524(9) 0.53501(9) 0.0375(4) Uani 1 1 d . . . C17 C 0.4470(2) 0.47830(9) 0.59899(9) 0.0420(4) Uani 1 1 d . . . C18 C 0.5409(2) 0.42578(10) 0.63503(9) 0.0463(4) Uani 1 1 d . . . C19 C 0.56171(19) 0.35016(10) 0.60712(8) 0.0405(4) Uani 1 1 d . . . C20 C 0.69348(17) 0.33521(10) 0.29522(8) 0.0330(3) Uani 1 1 d . . . H3 H 0.3475(18) 0.1586(10) 0.4225(9) 0.036(4) Uiso 1 1 d . . . H5 H 0.6602(16) 0.3218(9) 0.4334(8) 0.027(4) Uiso 1 1 d . . . H8 H 0.3734(19) 0.2291(11) 0.6275(9) 0.039(5) Uiso 1 1 d . . . H9 H 0.358(2) 0.1114(11) 0.6979(10) 0.048(5) Uiso 1 1 d . . . H10 H 0.468(2) -0.0093(12) 0.6695(10) 0.049(5) Uiso 1 1 d . . . H11 H 0.5962(18) -0.0088(11) 0.5670(9) 0.039(5) Uiso 1 1 d . . . H12 H 0.6117(17) 0.1069(9) 0.4988(9) 0.028(4) Uiso 1 1 d . . . H131 H 0.226(3) 0.1617(16) 0.2604(14) 0.085(8) Uiso 1 1 d . . . H132 H 0.342(2) 0.1067(14) 0.2422(13) 0.073(7) Uiso 1 1 d . . . H133 H 0.268(3) 0.0880(14) 0.3110(13) 0.073(7) Uiso 1 1 d . . . H15 H 0.3347(19) 0.3633(11) 0.4611(10) 0.043(5) Uiso 1 1 d . . . H16 H 0.308(2) 0.4939(12) 0.5068(10) 0.047(5) Uiso 1 1 d . . . H17 H 0.436(2) 0.5329(12) 0.6197(10) 0.047(5) Uiso 1 1 d . . . H18 H 0.598(2) 0.4435(13) 0.6806(12) 0.063(6) Uiso 1 1 d . . . H19 H 0.631(2) 0.3121(12) 0.6318(11) 0.056(6) Uiso 1 1 d . . . H201 H 0.749(2) 0.3682(12) 0.3289(11) 0.049(5) Uiso 1 1 d . . . H202 H 0.642(2) 0.3723(13) 0.2601(11) 0.058(6) Uiso 1 1 d . . . H203 H 0.754(2) 0.3033(13) 0.2676(11) 0.059(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 N1 0.0474(7) 0.0229(5) 0.0198(5) -0.0002(4) 0.0052(5) 0.0018(5) C1 0.0262(6) 0.0250(6) 0.0209(6) 0.0004(4) 0.0038(5) 0.0023(5) C2 0.0275(6) 0.0247(6) 0.0229(6) -0.0004(5) 0.0025(5) -0.0005(5) C3 0.0307(7) 0.0245(6) 0.0233(6) 0.0020(5) 0.0059(5) 0.0006(5) C4 0.0340(7) 0.0254(6) 0.0206(6) 0.0007(5) 0.0038(5) 0.0029(5) C5 0.0314(7) 0.0262(6) 0.0252(6) -0.0025(5) 0.0017(5) -0.0020(5) C6 0.0271(6) 0.0264(6) 0.0253(6) -0.0001(5) 0.0048(5) -0.0007(5) C7 0.0301(6) 0.0251(6) 0.0207(6) -0.0001(5) 0.0009(5) 0.0006(5) C8 0.0373(8) 0.0338(7) 0.0281(7) 0.0016(6) 0.0078(6) 0.0096(6) C9 0.0412(8) 0.0436(9) 0.0289(7) 0.0074(6) 0.0135(6) 0.0057(7) C10 0.0415(8) 0.0306(7) 0.0323(7) 0.0065(6) 0.0055(6) -0.0024(6) C11 0.0349(7) 0.0245(6) 0.0294(7) -0.0014(5) 0.0017(5) 0.0004(5) C12 0.0312(7) 0.0262(6) 0.0241(6) -0.0028(5) 0.0040(5) -0.0003(5) C13 0.0349(7) 0.0325(7) 0.0260(6) -0.0009(5) 0.0018(6) -0.0071(6) C14 0.0372(7) 0.0237(6) 0.0258(6) -0.0009(5) 0.0074(5) 0.0028(5) C15 0.0305(7) 0.0327(7) 0.0333(7) 0.0060(6) 0.0084(6) 0.0024(6) C16 0.0407(8) 0.0311(7) 0.0438(8) 0.0099(6) 0.0175(7) 0.0101(6) C17 0.0601(11) 0.0263(7) 0.0433(9) 0.0002(6) 0.0210(8) 0.0071(7) C18 0.0686(12) 0.0334(8) 0.0355(8) -0.0097(7) 0.0009(8) 0.0068(8) C19 0.0555(10) 0.0313(7) 0.0316(7) -0.0061(6) -0.0060(7) 0.0112(7) C20 0.0343(7) 0.0371(8) 0.0285(7) -0.0020(6) 0.0070(6) -0.0090(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 N1 C7 1.4109(17) . ? N1 C14 1.4237(17) . ? N1 C4 1.4276(16) . ? C1 C6 1.4036(18) . ? C1 C2 1.4037(18) . ? C1 C1 1.500(2) 2_655 ? C2 C3 1.3973(18) . ? C2 C13 1.5055(19) . ? C3 C4 1.3902(19) . ? C3 H3 0.977(18) . ? C4 C5 1.3904(19) . ? C5 C6 1.3947(18) . ? C5 H5 0.962(16) . ? C6 C20 1.5028(19) . ? C7 C12 1.3956(18) . ? C7 C8 1.3997(19) . ? C8 C9 1.389(2) . ? C8 H8 0.973(18) . ? C9 C10 1.385(2) . ? C9 H9 0.98(2) . ? C10 C11 1.377(2) . ? C10 H10 1.01(2) . ? C11 C12 1.3873(19) . ? C11 H11 0.985(18) . ? C12 H12 0.984(16) . ? C13 H131 0.97(3) . ? C13 H132 0.96(2) . ? C13 H133 1.01(2) . ? C14 C19 1.387(2) . ? C14 C15 1.390(2) . ? C15 C16 1.388(2) . ? C15 H15 1.004(19) . ? C16 C17 1.374(3) . ? C16 H16 1.016(19) . ? C17 C18 1.382(3) . ? C17 H17 1.001(19) . ? C18 C19 1.390(2) . ? C18 H18 1.01(2) . ? C19 H19 1.00(2) . ? C20 H201 0.95(2) . ? C20 H202 0.99(2) . ? C20 H203 0.99(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 C7 N1 C14 120.83(11) . . ? C7 N1 C4 120.10(11) . . ? C14 N1 C4 117.87(11) . . ? C6 C1 C2 119.64(11) . . ? C6 C1 C1 119.11(12) . 2_655 ? C2 C1 C1 121.16(12) . 2_655 ? C3 C2 C1 119.56(12) . . ? C3 C2 C13 119.11(12) . . ? C1 C2 C13 121.28(12) . . ? C4 C3 C2 120.90(12) . . ? C4 C3 H3 119.3(10) . . ? C2 C3 H3 119.8(10) . . ? C3 C4 C5 119.30(12) . . ? C3 C4 N1 121.27(12) . . ? C5 C4 N1 119.41(12) . . ? C4 C5 C6 120.91(13) . . ? C4 C5 H5 119.1(9) . . ? C6 C5 H5 120.0(10) . . ? C5 C6 C1 119.67(12) . . ? C5 C6 C20 119.84(12) . . ? C1 C6 C20 120.48(12) . . ? C12 C7 C8 118.68(12) . . ? C12 C7 N1 119.87(12) . . ? C8 C7 N1 121.44(12) . . ? C9 C8 C7 119.95(13) . . ? C9 C8 H8 121.7(11) . . ? C7 C8 H8 118.3(11) . . ? C10 C9 C8 121.01(14) . . ? C10 C9 H9 119.7(11) . . ? C8 C9 H9 119.2(11) . . ? C11 C10 C9 119.00(14) . . ? C11 C10 H10 121.4(11) . . ? C9 C10 H10 119.6(11) . . ? C10 C11 C12 121.01(14) . . ? C10 C11 H11 121.6(10) . . ? C12 C11 H11 117.4(10) . . ? C11 C12 C7 120.34(13) . . ? C11 C12 H12 119.9(9) . . ? C7 C12 H12 119.7(9) . . ? C2 C13 H131 111.9(15) . . ? C2 C13 H132 111.9(14) . . ? H131 C13 H132 104(2) . . ? C2 C13 H133 114.6(14) . . ? H131 C13 H133 106(2) . . ? H132 C13 H133 107.5(18) . . ? C19 C14 C15 119.37(13) . . ? C19 C14 N1 120.29(13) . . ? C15 C14 N1 120.33(13) . . ? C16 C15 C14 119.96(15) . . ? C16 C15 H15 119.2(11) . . ? C14 C15 H15 120.8(11) . . ? C17 C16 C15 120.74(15) . . ? C17 C16 H16 120.5(11) . . ? C15 C16 H16 118.7(11) . . ? C16 C17 C18 119.44(15) . . ? C16 C17 H17 121.8(11) . . ? C18 C17 H17 118.7(11) . . ? C17 C18 C19 120.55(16) . . ? C17 C18 H18 119.7(12) . . ? C19 C18 H18 119.7(12) . . ? C14 C19 C18 119.91(15) . . ? C14 C19 H19 118.6(12) . . ? C18 C19 H19 121.5(12) . . ? C6 C20 H201 111.9(12) . . ? C6 C20 H202 110.9(12) . . ? H201 C20 H202 106.3(17) . . ? C6 C20 H203 112.3(12) . . ? H201 C20 H203 109.5(17) . . ? H202 C20 H203 105.6(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 C6 C1 C2 C3 0.45(19) . . . . ? C1 C1 C2 C3 -176.25(12) 2_655 . . . ? C6 C1 C2 C13 177.83(13) . . . . ? C1 C1 C2 C13 1.12(19) 2_655 . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C13 C2 C3 C4 -178.00(13) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C2 C3 C4 N1 177.97(12) . . . . ? C7 N1 C4 C3 44.55(19) . . . . ? C14 N1 C4 C3 -123.02(15) . . . . ? C7 N1 C4 C5 -137.21(14) . . . . ? C14 N1 C4 C5 55.22(18) . . . . ? C3 C4 C5 C6 1.2(2) . . . . ? N1 C4 C5 C6 -177.03(12) . . . . ? C4 C5 C6 C1 -1.4(2) . . . . ? C4 C5 C6 C20 178.51(13) . . . . ? C2 C1 C6 C5 0.5(2) . . . . ? C1 C1 C6 C5 177.27(12) 2_655 . . . ? C2 C1 C6 C20 -179.38(13) . . . . ? C1 C1 C6 C20 -2.60(19) 2_655 . . . ? C14 N1 C7 C12 -157.22(13) . . . . ? C4 N1 C7 C12 35.58(19) . . . . ? C14 N1 C7 C8 23.1(2) . . . . ? C4 N1 C7 C8 -144.10(14) . . . . ? C12 C7 C8 C9 -0.2(2) . . . . ? N1 C7 C8 C9 179.47(14) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C10 C11 C12 C7 -0.5(2) . . . . ? C8 C7 C12 C11 0.7(2) . . . . ? N1 C7 C12 C11 -179.00(13) . . . . ? C7 N1 C14 C19 52.6(2) . . . . ? C4 N1 C14 C19 -139.95(15) . . . . ? C7 N1 C14 C15 -127.75(15) . . . . ? C4 N1 C14 C15 39.7(2) . . . . ? C19 C14 C15 C16 -0.5(2) . . . . ? N1 C14 C15 C16 179.80(13) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? C15 C16 C17 C18 1.1(3) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? C15 C14 C19 C18 1.5(3) . . . . ? N1 C14 C19 C18 -178.79(16) . . . . ? C17 C18 C19 C14 -1.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.317 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.044