# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 836390' #TrackingRef 'web_deposit_cif_file_0_NidhinPaul_1362362793.acta.cif' _cell_special_details ? #Added by publCIF _audit_update_record ; 2013-03-03 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic (Z)-1,4-diphenyl-2-(4-toluidino)-2-butane-1,4-dione _chemical_name_common (Z)-1,4-diphenyl-2-(4-toluidino)-2-butane-1,4-dione _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N O2' _chemical_formula_weight 341.39 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.0504(7) _cell_length_b 8.6750(7) _cell_length_c 21.4200(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.066(6) _cell_angle_gamma 90.00 _cell_volume 1819.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details '(CrysAlis Pro; Oxford Diffraction, 2009)' _exptl_special_details ? _diffrn_ambient_temperature 293(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 'Oxford Diffraction Xcalibur-S' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11790 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3197 _reflns_number_gt 2314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Pro (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2009)' _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^)+(0.1000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3197 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.073 _refine_ls_shift/su_mean 0.013 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 0.37127(17) 0.31998(17) 0.00875(7) 0.0481(4) Uani 1 1 d . . . H1 H 0.4031 0.2584 -0.0158 0.058 Uiso 1 1 calc R . . O2 O 0.12928(14) 0.42251(15) 0.05623(6) 0.0556(4) Uani 1 1 d . . . O1 O 0.35215(15) 0.20998(15) -0.10866(6) 0.0580(4) Uani 1 1 d . . . C9 C 0.26248(18) 0.4046(2) -0.01978(8) 0.0415(4) Uani 1 1 d . . . C17 C 0.44023(18) 0.3197(2) 0.07454(8) 0.0430(5) Uani 1 1 d . . . C5 C 0.17988(19) 0.2932(2) -0.19661(8) 0.0443(5) Uani 1 1 d . . . C11 C 0.18832(17) 0.6663(2) 0.02108(7) 0.0419(5) Uani 1 1 d . . . C8 C 0.20487(19) 0.3977(2) -0.08384(8) 0.0447(5) Uani 1 1 d . . . H8 H 0.1312 0.4620 -0.1002 0.054 Uiso 1 1 calc R . . C7 C 0.2518(2) 0.2967(2) -0.12736(8) 0.0438(5) Uani 1 1 d . . . C10 C 0.18917(17) 0.4962(2) 0.02263(7) 0.0406(4) Uani 1 1 d . . . C6 C 0.2425(2) 0.2177(2) -0.23925(9) 0.0555(5) Uani 1 1 d . . . H6 H 0.3271 0.1712 -0.2242 0.067 Uiso 1 1 calc R . . C18 C 0.4883(2) 0.1811(2) 0.10304(10) 0.0562(5) Uani 1 1 d . . . H18 H 0.4721 0.0899 0.0797 0.067 Uiso 1 1 calc R . . C20 C 0.5852(2) 0.3101(3) 0.20294(10) 0.0584(6) Uani 1 1 d . . . C21 C 0.46541(18) 0.4532(2) 0.11017(8) 0.0495(5) Uani 1 1 d . . . H21 H 0.4355 0.5475 0.0915 0.059 Uiso 1 1 calc R . . C22 C 0.53509(19) 0.4471(3) 0.17361(9) 0.0560(5) Uani 1 1 d . . . H22 H 0.5488 0.5378 0.1973 0.067 Uiso 1 1 calc R . . C12 C 0.2420(2) 0.7497(2) -0.02271(9) 0.0523(5) Uani 1 1 d . . . H12 H 0.2808 0.6992 -0.0526 0.063 Uiso 1 1 calc R . . C2 C 0.0567(2) 0.2767(3) -0.32662(10) 0.0620(6) Uani 1 1 d . . . H2 H 0.0151 0.2700 -0.3700 0.074 Uiso 1 1 calc R . . C13 C 0.2371(2) 0.9088(3) -0.02140(11) 0.0699(6) Uani 1 1 d . . . H13 H 0.2716 0.9658 -0.0510 0.084 Uiso 1 1 calc R . . C4 C 0.0549(2) 0.3624(3) -0.22059(9) 0.0650(6) Uani 1 1 d . . . H4 H 0.0117 0.4155 -0.1930 0.078 Uiso 1 1 calc R . . C1 C 0.1817(2) 0.2102(2) -0.30359(10) 0.0637(6) Uani 1 1 d . . . H1A H 0.2257 0.1597 -0.3315 0.076 Uiso 1 1 calc R . . C19 C 0.5603(2) 0.1783(3) 0.16611(10) 0.0660(7) Uani 1 1 d . . . H19 H 0.5930 0.0845 0.1844 0.079 Uiso 1 1 calc R . . C16 C 0.1336(2) 0.7433(3) 0.06593(10) 0.0580(6) Uani 1 1 d . . . H16 H 0.0980 0.6876 0.0955 0.070 Uiso 1 1 calc R . . C15 C 0.1313(2) 0.9006(3) 0.06711(11) 0.0739(7) Uani 1 1 d . . . H15 H 0.0954 0.9517 0.0978 0.089 Uiso 1 1 calc R . . C14 C 0.1818(2) 0.9832(3) 0.02319(13) 0.0777(7) Uani 1 1 d . . . H14 H 0.1785 1.0903 0.0236 0.093 Uiso 1 1 calc R . . C3 C -0.0068(2) 0.3534(3) -0.28528(10) 0.0741(7) Uani 1 1 d . . . H3 H -0.0914 0.3994 -0.3008 0.089 Uiso 1 1 calc R . . C23 C 0.6651(3) 0.3074(3) 0.27141(11) 0.0891(9) Uani 1 1 d . . . H23A H 0.7462 0.3686 0.2754 0.134 Uiso 1 1 calc R . . H23B H 0.6900 0.2032 0.2839 0.134 Uiso 1 1 calc R . . H23C H 0.6102 0.3489 0.2987 0.134 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 0.0506(10) 0.0521(10) 0.0397(9) 0.0018(7) 0.0064(7) 0.0063(7) O2 0.0588(9) 0.0652(9) 0.0457(8) 0.0145(6) 0.0180(6) -0.0029(7) O1 0.0667(10) 0.0558(9) 0.0494(8) 0.0011(6) 0.0087(7) 0.0134(7) C9 0.0460(11) 0.0400(10) 0.0384(10) 0.0070(7) 0.0092(8) -0.0047(8) C17 0.0387(10) 0.0490(11) 0.0406(10) 0.0063(8) 0.0073(8) -0.0014(8) C5 0.0532(12) 0.0424(10) 0.0382(10) 0.0010(8) 0.0125(9) -0.0064(8) C11 0.0369(10) 0.0503(12) 0.0349(9) -0.0007(8) 0.0007(8) -0.0013(8) C8 0.0492(11) 0.0476(11) 0.0365(9) 0.0039(8) 0.0082(8) 0.0012(9) C7 0.0486(12) 0.0414(10) 0.0405(10) 0.0049(8) 0.0083(8) -0.0021(9) C10 0.0389(10) 0.0503(11) 0.0303(9) 0.0043(8) 0.0028(8) -0.0027(8) C6 0.0619(13) 0.0551(13) 0.0484(11) -0.0080(9) 0.0104(10) 0.0046(10) C18 0.0561(13) 0.0482(12) 0.0595(13) 0.0050(9) 0.0030(10) 0.0026(9) C20 0.0436(12) 0.0778(16) 0.0486(11) 0.0093(11) -0.0001(9) -0.0053(10) C21 0.0431(11) 0.0498(12) 0.0518(11) 0.0057(9) 0.0028(9) -0.0040(9) C22 0.0478(12) 0.0634(14) 0.0526(12) -0.0052(10) 0.0026(9) -0.0094(10) C12 0.0521(12) 0.0497(12) 0.0542(12) 0.0038(9) 0.0102(9) -0.0040(10) C2 0.0727(16) 0.0724(15) 0.0382(10) -0.0039(10) 0.0072(10) -0.0063(12) C13 0.0692(15) 0.0537(14) 0.0826(16) 0.0131(12) 0.0083(12) -0.0095(11) C4 0.0616(14) 0.0888(17) 0.0441(11) -0.0060(11) 0.0111(10) 0.0138(12) C1 0.0757(16) 0.0708(15) 0.0461(12) -0.0146(10) 0.0170(11) 0.0017(12) C19 0.0615(15) 0.0636(15) 0.0648(14) 0.0226(11) -0.0026(12) 0.0047(11) C16 0.0516(13) 0.0699(15) 0.0526(12) -0.0101(10) 0.0120(10) 0.0007(11) C15 0.0650(15) 0.0680(17) 0.0854(17) -0.0274(13) 0.0103(13) 0.0061(12) C14 0.0638(15) 0.0494(14) 0.110(2) -0.0120(14) -0.0020(14) 0.0015(11) C3 0.0650(15) 0.104(2) 0.0491(13) 0.0014(12) 0.0034(11) 0.0139(13) C23 0.0746(18) 0.120(2) 0.0591(15) 0.0161(14) -0.0130(13) -0.0050(15) _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 C9 1.344(2) . ? N1 C17 1.423(2) . ? N1 H1 0.8600 . ? O2 C10 1.2187(19) . ? O1 C7 1.249(2) . ? C9 C8 1.365(2) . ? C9 C10 1.517(2) . ? C17 C21 1.379(3) . ? C17 C18 1.385(3) . ? C5 C4 1.382(3) . ? C5 C6 1.386(3) . ? C5 C7 1.496(2) . ? C11 C16 1.383(3) . ? C11 C12 1.387(2) . ? C11 C10 1.476(3) . ? C8 C7 1.435(3) . ? C8 H8 0.9300 . ? C6 C1 1.377(3) . ? C6 H6 0.9300 . ? C18 C19 1.381(3) . ? C18 H18 0.9300 . ? C20 C19 1.379(3) . ? C20 C22 1.385(3) . ? C20 C23 1.505(3) . ? C21 C22 1.382(2) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C2 C1 1.368(3) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C13 C14 1.371(3) . ? C13 H13 0.9300 . ? C4 C3 1.386(3) . ? C4 H4 0.9300 . ? C1 H1A 0.9300 . ? C19 H19 0.9300 . ? C16 C15 1.365(3) . ? C16 H16 0.9300 . ? C15 C14 1.368(3) . ? C15 H15 0.9300 . ? C14 H14 0.9300 . ? C3 H3 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C9 N1 C17 127.98(16) . . ? C9 N1 H1 116.0 . . ? C17 N1 H1 116.0 . . ? N1 C9 C8 123.36(17) . . ? N1 C9 C10 117.98(14) . . ? C8 C9 C10 118.15(16) . . ? C21 C17 C18 118.90(17) . . ? C21 C17 N1 122.29(16) . . ? C18 C17 N1 118.76(17) . . ? C4 C5 C6 118.08(17) . . ? C4 C5 C7 123.68(16) . . ? C6 C5 C7 118.23(18) . . ? C16 C11 C12 119.66(19) . . ? C16 C11 C10 117.95(16) . . ? C12 C11 C10 122.38(16) . . ? C9 C8 C7 123.56(17) . . ? C9 C8 H8 118.2 . . ? C7 C8 H8 118.2 . . ? O1 C7 C8 121.32(16) . . ? O1 C7 C5 118.68(16) . . ? C8 C7 C5 120.00(16) . . ? O2 C10 C11 122.46(16) . . ? O2 C10 C9 116.75(17) . . ? C11 C10 C9 120.76(14) . . ? C1 C6 C5 121.1(2) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C19 C18 C17 119.97(19) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C19 C20 C22 116.86(18) . . ? C19 C20 C23 122.2(2) . . ? C22 C20 C23 121.0(2) . . ? C17 C21 C22 120.07(18) . . ? C17 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C20 122.02(19) . . ? C21 C22 H22 119.0 . . ? C20 C22 H22 119.0 . . ? C13 C12 C11 119.1(2) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C1 C2 C3 119.59(19) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C5 C4 C3 120.68(19) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C2 C1 C6 120.30(19) . . ? C2 C1 H1A 119.8 . . ? C6 C1 H1A 119.8 . . ? C20 C19 C18 122.2(2) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C15 C16 C11 120.5(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C16 C15 C14 120.0(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 C17 N1 C9 C8 179.05(17) . . . . ? C17 N1 C9 C10 -9.2(3) . . . . ? C9 N1 C17 C21 -40.4(3) . . . . ? C9 N1 C17 C18 142.1(2) . . . . ? N1 C9 C8 C7 1.7(3) . . . . ? C10 C9 C8 C7 -170.04(16) . . . . ? C9 C8 C7 O1 -1.6(3) . . . . ? C9 C8 C7 C5 178.16(16) . . . . ? C4 C5 C7 O1 168.1(2) . . . . ? C6 C5 C7 O1 -12.5(3) . . . . ? C4 C5 C7 C8 -11.6(3) . . . . ? C6 C5 C7 C8 167.81(17) . . . . ? C16 C11 C10 O2 9.2(2) . . . . ? C12 C11 C10 O2 -171.88(17) . . . . ? C16 C11 C10 C9 -172.68(16) . . . . ? C12 C11 C10 C9 6.3(2) . . . . ? N1 C9 C10 O2 -67.1(2) . . . . ? C8 C9 C10 O2 105.05(19) . . . . ? N1 C9 C10 C11 114.64(18) . . . . ? C8 C9 C10 C11 -73.2(2) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C7 C5 C6 C1 179.94(18) . . . . ? C21 C17 C18 C19 -0.1(3) . . . . ? N1 C17 C18 C19 177.46(18) . . . . ? C18 C17 C21 C22 -1.3(3) . . . . ? N1 C17 C21 C22 -178.77(17) . . . . ? C17 C21 C22 C20 2.0(3) . . . . ? C19 C20 C22 C21 -1.1(3) . . . . ? C23 C20 C22 C21 177.76(19) . . . . ? C16 C11 C12 C13 -1.3(3) . . . . ? C10 C11 C12 C13 179.76(17) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? C6 C5 C4 C3 1.3(3) . . . . ? C7 C5 C4 C3 -179.32(19) . . . . ? C3 C2 C1 C6 1.1(4) . . . . ? C5 C6 C1 C2 -0.6(3) . . . . ? C22 C20 C19 C18 -0.4(3) . . . . ? C23 C20 C19 C18 -179.2(2) . . . . ? C17 C18 C19 C20 0.9(3) . . . . ? C12 C11 C16 C15 0.4(3) . . . . ? C10 C11 C16 C15 179.39(18) . . . . ? C11 C16 C15 C14 0.8(3) . . . . ? C16 C15 C14 C13 -1.2(4) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C5 C4 C3 C2 -0.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.158 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.036