Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Radhakrishnan, T. P.' 'Gangopadhyay, P.' 'Jayanty, S.' _publ_contact_author_name 'Dr T P Radhakrishnan' _publ_contact_author_address ; University of Hyderabad Hyderabad 500 046 INDIA ; _publ_contact_author_email 'TPRSC@UOHYD.ERNET.IN' _publ_section_title ; Steering Molecular Dipoles from Centrosymmetric to Noncentrosymmetric and SHG Active Assembly Using Remote Functionality and Complexation ; data_DMEDQ-TPA _database_code_CSD 181468 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7,7-bis(N,N-dimethylethylenediamino)-8,8- dicyanoquinodimethane : terephthalic acid ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 N6 O4' _chemical_formula_weight 492.58 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 Cc _symmetry_Int_Tables_number 9 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' _cell_length_a 13.2413(11) _cell_length_b 12.5696(8) _cell_length_c 15.3847(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.004(6) _cell_angle_gamma 90.00 _cell_volume 2550.8(3) _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 Plate _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _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 3068 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.96 _reflns_number_total 3068 _reflns_number_gt 1394 _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 w=1/[\s^2^(Fo^2^)+(0.0452P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 2914 _refine_ls_number_parameters 335 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.950 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3583(4) 0.2642(4) 0.7611(3) 0.0567(16) Uani 1 d . . . H1 H 0.3342 0.2006 0.7615 0.068 Uiso 1 calc R . . N2 N 0.4998(4) 0.3671(4) 0.7489(3) 0.0442(13) Uani 1 d . . . H2 H 0.4719 0.4151 0.7787 0.053 Uiso 1 calc R . . N3 N 0.5102(6) -0.1819(5) 0.4445(5) 0.087(2) Uani 1 d . . . N4 N 0.8094(5) -0.1122(6) 0.5739(4) 0.078(2) Uani 1 d . . . N5 N 0.2281(5) 0.2847(4) 0.9210(4) 0.0590(17) Uani 1 d . . . H5 H 0.2421 0.2194 0.8996 0.071 Uiso 1 calc R . . N6 N 0.5549(4) 0.5257(4) 0.5952(3) 0.0451(13) Uani 1 d . . . H6 H 0.5019 0.5429 0.6264 0.054 Uiso 1 calc R . . O25 O 0.2561(3) 0.1043(3) 0.8343(3) 0.0497(11) Uani 1 d . . . O26 O 0.2553(3) 0.0382(3) 0.9675(3) 0.0569(12) Uani 1 d . . . O27 O 0.4188(4) -0.3782(4) 0.6791(3) 0.0725(15) Uani 1 d . . . O28 O 0.4319(5) -0.4435(4) 0.8118(3) 0.090(2) Uani 1 d . . . C7 C 0.4969(4) 0.1831(4) 0.6979(3) 0.0363(14) Uani 1 d . . . C8 C 0.4399(5) 0.1313(5) 0.6300(4) 0.0410(14) Uani 1 d . . . H8 H 0.3744 0.1549 0.6140 0.049 Uiso 1 calc R . . C9 C 0.4769(5) 0.0470(5) 0.5859(4) 0.0441(15) Uani 1 d . . . H9 H 0.4359 0.0127 0.5424 0.053 Uiso 1 calc R . . C10 C 0.5767(4) 0.0129(5) 0.6067(3) 0.0389(14) Uani 1 d . . . C11 C 0.6334(5) 0.0622(5) 0.6748(4) 0.0430(15) Uani 1 d . . . H11 H 0.6992 0.0390 0.6902 0.052 Uiso 1 calc R . . C12 C 0.5943(4) 0.1459(5) 0.7210(4) 0.0405(14) Uani 1 d . . . H12 H 0.6335 0.1769 0.7673 0.049 Uiso 1 calc R . . C13 C 0.4524(4) 0.2764(5) 0.7386(4) 0.0411(15) Uani 1 d . . . C14 C 0.6202(5) -0.0722(5) 0.5564(4) 0.0482(16) Uani 1 d . . . C15 C 0.5606(6) -0.1316(6) 0.4945(5) 0.062(2) Uani 1 d . . . C16 C 0.7251(6) -0.0947(5) 0.5656(4) 0.0542(17) Uani 1 d . . . C17 C 0.2936(7) 0.3505(6) 0.7849(6) 0.091(3) Uani 1 d . . . H17A H 0.3195 0.4160 0.7621 0.109 Uiso 1 calc R . . H17B H 0.2266 0.3391 0.7556 0.109 Uiso 1 calc R . . C18 C 0.2833(9) 0.3650(6) 0.8716(6) 0.119(4) Uani 1 d . . . H18A H 0.2497 0.4329 0.8776 0.142 Uiso 1 calc R . . H18B H 0.3509 0.3718 0.9007 0.142 Uiso 1 calc R . . C19 C 0.1177(6) 0.2960(8) 0.9150(6) 0.099(3) Uani 1 d . . . H19A H 0.0889 0.2392 0.9465 0.149 Uiso 1 calc R . . H19B H 0.0914 0.2932 0.8549 0.149 Uiso 1 calc R . . H19C H 0.1002 0.3630 0.9397 0.149 Uiso 1 calc R . . C20 C 0.2727(7) 0.2887(6) 1.0130(5) 0.088(3) Uani 1 d . . . H20A H 0.3450 0.2815 1.0146 0.132 Uiso 1 calc R . . H20B H 0.2456 0.2317 1.0454 0.132 Uiso 1 calc R . . H20C H 0.2563 0.3556 1.0385 0.132 Uiso 1 calc R . . C21 C 0.5960(5) 0.3949(5) 0.7145(4) 0.0501(16) Uani 1 d . . . H21A H 0.6436 0.3371 0.7268 0.060 Uiso 1 calc R . . H21B H 0.6236 0.4575 0.7448 0.060 Uiso 1 calc R . . C22 C 0.5867(5) 0.4165(5) 0.6176(4) 0.0485(16) Uani 1 d . . . H22A H 0.6516 0.4031 0.5950 0.058 Uiso 1 calc R . . H22B H 0.5379 0.3673 0.5892 0.058 Uiso 1 calc R . . C23 C 0.6387(6) 0.6035(5) 0.6172(5) 0.066(2) Uani 1 d . . . H23A H 0.6604 0.5989 0.6783 0.099 Uiso 1 calc R . . H23B H 0.6149 0.6743 0.6036 0.099 Uiso 1 calc R . . H23C H 0.6947 0.5874 0.5838 0.099 Uiso 1 calc R . . C24 C 0.5210(5) 0.5327(6) 0.5016(4) 0.066(2) Uani 1 d . . . H24A H 0.4663 0.4837 0.4880 0.100 Uiso 1 calc R . . H24B H 0.5764 0.5152 0.4679 0.100 Uiso 1 calc R . . H24C H 0.4983 0.6037 0.4879 0.100 Uiso 1 calc R . . C29 C 0.3108(5) -0.0732(5) 0.8567(4) 0.0381(14) Uani 1 d . . . C30 C 0.3046(4) -0.1666(5) 0.9036(3) 0.0407(15) Uani 1 d . . . H30 H 0.2771 -0.1648 0.9571 0.049 Uiso 1 calc R . . C31 C 0.3382(5) -0.2623(5) 0.8728(4) 0.0475(17) Uani 1 d . . . H31 H 0.3341 -0.3238 0.9059 0.057 Uiso 1 calc R . . C32 C 0.3779(4) -0.2665(5) 0.7927(4) 0.0371(13) Uani 1 d . . . C33 C 0.3853(5) -0.1738(5) 0.7458(4) 0.0485(17) Uani 1 d . . . H33 H 0.4121 -0.1763 0.6919 0.058 Uiso 1 calc R . . C34 C 0.3541(5) -0.0781(5) 0.7768(4) 0.0458(16) Uani 1 d . . . H34 H 0.3617 -0.0163 0.7448 0.055 Uiso 1 calc R . . C35 C 0.2725(4) 0.0306(5) 0.8907(4) 0.0419(15) Uani 1 d . . . C36 C 0.4147(5) -0.3717(5) 0.7603(4) 0.0457(15) Uani 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 0.054(3) 0.046(3) 0.076(4) 0.021(3) 0.038(3) 0.020(3) N2 0.056(3) 0.033(3) 0.045(3) 0.004(2) 0.014(3) 0.009(3) N3 0.100(6) 0.076(5) 0.086(5) -0.036(4) 0.007(4) -0.012(4) N4 0.068(4) 0.101(5) 0.065(4) -0.014(4) 0.009(3) 0.038(4) N5 0.085(5) 0.029(3) 0.070(4) -0.001(3) 0.046(4) 0.004(3) N6 0.050(3) 0.046(3) 0.042(3) -0.004(2) 0.016(2) -0.001(3) O25 0.063(3) 0.032(2) 0.056(2) 0.001(2) 0.014(2) 0.002(2) O26 0.069(3) 0.054(3) 0.051(3) -0.007(2) 0.024(2) 0.010(3) O27 0.102(4) 0.066(3) 0.052(3) -0.008(3) 0.021(3) 0.032(3) O28 0.166(6) 0.044(3) 0.064(3) -0.003(3) 0.029(4) 0.042(4) C7 0.041(4) 0.033(3) 0.037(3) 0.007(3) 0.017(3) 0.003(3) C8 0.035(3) 0.042(3) 0.047(3) 0.002(3) 0.010(3) 0.000(3) C9 0.044(4) 0.046(4) 0.042(3) -0.001(3) 0.004(3) 0.001(3) C10 0.044(4) 0.037(3) 0.036(3) 0.001(3) 0.008(3) 0.002(3) C11 0.038(3) 0.037(3) 0.053(4) 0.004(3) 0.000(3) 0.009(3) C12 0.043(3) 0.039(4) 0.038(3) -0.001(3) -0.001(3) 0.012(3) C13 0.046(4) 0.038(3) 0.040(3) 0.007(3) 0.012(3) 0.011(3) C14 0.058(4) 0.041(4) 0.047(4) -0.007(3) 0.015(3) 0.007(3) C15 0.073(6) 0.055(5) 0.062(4) -0.007(4) 0.024(4) 0.001(4) C16 0.072(5) 0.050(4) 0.043(3) -0.010(3) 0.014(3) 0.019(4) C17 0.104(7) 0.068(5) 0.112(7) 0.030(5) 0.072(6) 0.045(5) C18 0.224(12) 0.037(5) 0.112(7) 0.001(5) 0.113(8) 0.005(6) C19 0.063(5) 0.133(10) 0.104(6) -0.032(6) 0.018(5) 0.019(6) C20 0.106(7) 0.080(6) 0.083(6) -0.031(5) 0.040(5) -0.008(5) C21 0.053(4) 0.034(3) 0.064(4) 0.009(3) 0.003(3) -0.001(3) C22 0.042(4) 0.040(4) 0.066(4) -0.010(3) 0.017(3) -0.003(3) C23 0.080(5) 0.056(4) 0.064(4) 0.007(4) 0.009(4) -0.023(4) C24 0.059(5) 0.090(6) 0.050(4) -0.002(4) 0.007(3) 0.011(4) C29 0.036(3) 0.039(3) 0.040(3) -0.007(3) 0.007(3) -0.001(3) C30 0.051(4) 0.040(3) 0.032(3) -0.001(3) 0.010(3) -0.002(3) C31 0.065(5) 0.039(4) 0.041(3) 0.004(3) 0.021(3) 0.006(3) C32 0.039(3) 0.036(3) 0.038(3) -0.008(3) 0.008(2) 0.005(3) C33 0.056(4) 0.048(4) 0.045(3) -0.005(3) 0.026(3) 0.004(3) C34 0.053(4) 0.037(4) 0.050(4) 0.008(3) 0.025(3) 0.006(3) C35 0.042(4) 0.028(3) 0.058(4) -0.007(3) 0.015(3) -0.011(3) C36 0.050(4) 0.044(4) 0.043(3) -0.012(3) 0.005(3) 0.006(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 N1 C13 1.331(7) . ? N1 C17 1.449(8) . ? N2 C13 1.304(7) . ? N2 C21 1.463(7) . ? N3 C15 1.161(9) . ? N4 C16 1.134(9) . ? N5 C19 1.464(9) . ? N5 C20 1.486(9) . ? N5 C18 1.493(9) . ? N6 C22 1.468(8) . ? N6 C24 1.474(7) . ? N6 C23 1.496(8) . ? O25 C35 1.274(7) . ? O26 C35 1.227(6) . ? O27 C36 1.257(7) . ? O28 C36 1.210(7) . ? C7 C12 1.388(8) . ? C7 C8 1.395(8) . ? C7 C13 1.477(8) . ? C8 C9 1.372(8) . ? C9 C10 1.400(8) . ? C10 C11 1.381(8) . ? C10 C14 1.468(8) . ? C11 C12 1.394(8) . ? C14 C15 1.398(10) . ? C14 C16 1.413(11) . ? C17 C18 1.364(10) . ? C21 C22 1.510(8) . ? C29 C30 1.384(8) . ? C29 C34 1.402(8) . ? C29 C35 1.509(8) . ? C30 C31 1.381(8) . ? C31 C32 1.382(7) . ? C32 C33 1.378(8) . ? C32 C36 1.510(8) . ? C33 C34 1.372(8) . ? 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 C13 N1 C17 124.5(6) . . ? C13 N2 C21 126.1(5) . . ? C19 N5 C20 111.7(6) . . ? C19 N5 C18 115.6(7) . . ? C20 N5 C18 106.9(7) . . ? C22 N6 C24 109.9(5) . . ? C22 N6 C23 111.5(5) . . ? C24 N6 C23 109.7(5) . . ? C12 C7 C8 117.6(5) . . ? C12 C7 C13 123.7(6) . . ? C8 C7 C13 118.6(5) . . ? C9 C8 C7 122.6(6) . . ? C8 C9 C10 119.5(6) . . ? C11 C10 C9 118.5(5) . . ? C11 C10 C14 121.0(6) . . ? C9 C10 C14 120.5(5) . . ? C10 C11 C12 121.5(6) . . ? C7 C12 C11 120.1(6) . . ? N2 C13 N1 121.4(5) . . ? N2 C13 C7 122.7(5) . . ? N1 C13 C7 115.8(6) . . ? C15 C14 C16 116.9(6) . . ? C15 C14 C10 121.6(6) . . ? C16 C14 C10 121.4(6) . . ? N3 C15 C14 178.6(8) . . ? N4 C16 C14 179.2(7) . . ? C18 C17 N1 117.4(7) . . ? C17 C18 N5 120.2(8) . . ? N2 C21 C22 113.7(5) . . ? N6 C22 C21 113.3(5) . . ? C30 C29 C34 117.8(5) . . ? C30 C29 C35 121.1(5) . . ? C34 C29 C35 121.1(5) . . ? C29 C30 C31 121.7(5) . . ? C30 C31 C32 119.9(6) . . ? C33 C32 C31 119.0(5) . . ? C33 C32 C36 121.8(5) . . ? C31 C32 C36 119.2(6) . . ? C34 C33 C32 121.4(5) . . ? C33 C34 C29 120.1(6) . . ? O26 C35 O25 124.3(6) . . ? O26 C35 C29 119.8(6) . . ? O25 C35 C29 115.8(5) . . ? O28 C36 O27 125.5(6) . . ? O28 C36 C32 119.0(5) . . ? O27 C36 C32 115.4(6) . . ? _diffrn_measured_fraction_theta_max 0.499 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.499 _refine_diff_density_max 0.19 _refine_diff_density_min -0.14 _refine_diff_density_rms 0.04 #------------------------------------------------------------------------ #===EOF #------------------------------------------------------------------------ data_DMEDQ _database_code_CSD 181469 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7,7-bis(N,N-dimethylethylenediamino)- 8,8-dicyanoquinodimethane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 N6' _chemical_formula_weight 326.45 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 P21/c _symmetry_Int_Tables_number 14 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 13.121(3) _cell_length_b 10.192(4) _cell_length_c 15.463(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.94(2) _cell_angle_gamma 90.00 _cell_volume 1918.1(9) _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 Cube _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _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 4384 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1053 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4384 _reflns_number_gt 1080 _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 w=1/[\s^2^(Fo^2^)+(0.0662P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1846 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2158 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1904 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2625(2) 0.0292(3) 0.3889(2) 0.0688(9) Uani 1 d . . . H1 H 0.2758 -0.0340 0.3578 0.083 Uiso 1 calc R . . N2 N 0.3021(2) 0.2408(3) 0.4384(2) 0.0618(8) Uani 1 d . . . H2 H 0.2373 0.2458 0.4397 0.074 Uiso 1 calc R . . N3 N 0.8062(3) -0.1148(4) 0.3110(3) 0.0908(12) Uani 1 d . . . N4 N 0.7163(3) 0.2726(4) 0.1803(3) 0.0994(13) Uani 1 d . . . N5 N 0.0721(2) 0.2172(4) 0.3909(2) 0.0822(10) Uani 1 d . . . N6 N 0.2449(3) 0.4542(3) 0.5362(2) 0.0743(9) Uani 1 d . . . C7 C 0.4211(3) 0.1246(3) 0.3748(2) 0.0515(8) Uani 1 d . . . C8 C 0.4820(3) 0.0094(3) 0.3876(2) 0.0568(9) Uani 1 d . . . H8 H 0.4642 -0.0614 0.4173 0.068 Uiso 1 calc R . . C9 C 0.5675(3) -0.0020(3) 0.3575(2) 0.0518(9) Uani 1 d . . . H9 H 0.6071 -0.0799 0.3682 0.062 Uiso 1 calc R . . C10 C 0.5966(2) 0.1001(3) 0.3112(2) 0.0498(8) Uani 1 d . . . C11 C 0.5345(3) 0.2157(3) 0.2982(2) 0.0599(10) Uani 1 d . . . H11 H 0.5516 0.2865 0.2681 0.072 Uiso 1 calc R . . C12 C 0.4494(3) 0.2268(3) 0.3286(2) 0.0575(9) Uani 1 d . . . H12 H 0.4096 0.3046 0.3181 0.069 Uiso 1 calc R . . C13 C 0.3254(3) 0.1333(4) 0.4026(2) 0.0535(9) Uani 1 d . . . C14 C 0.6841(3) 0.0882(3) 0.2775(2) 0.0547(9) Uani 1 d . . . C15 C 0.7514(3) -0.0232(4) 0.2950(3) 0.0629(10) Uani 1 d . . . C16 C 0.7038(3) 0.1884(4) 0.2245(3) 0.0678(11) Uani 1 d . . . C17 C 0.1724(3) 0.0102(4) 0.4212(3) 0.0865(14) Uani 1 d . . . H17A H 0.1955 0.0402 0.4852 0.104 Uiso 1 calc R . . H17B H 0.1567 -0.0829 0.4205 0.104 Uiso 1 calc R . . C18 C 0.0681(3) 0.0819(6) 0.3628(3) 0.1071(17) Uani 1 d . . . H18A H 0.0587 0.0776 0.2976 0.129 Uiso 1 calc R . . H18B H 0.0054 0.0393 0.3696 0.129 Uiso 1 calc R . . C19 C 0.0237(4) 0.2333(5) 0.4604(3) 0.1066(16) Uani 1 d . . . H19A H 0.0261 0.3241 0.4773 0.160 Uiso 1 calc R . . H19B H 0.0642 0.1822 0.5145 0.160 Uiso 1 calc R . . H19C H -0.0512 0.2041 0.4354 0.160 Uiso 1 calc R . . C20 C 0.0191(4) 0.3046(7) 0.3125(4) 0.161(3) Uani 1 d . . . H20A H 0.0236 0.3933 0.3346 0.242 Uiso 1 calc R . . H20B H -0.0567 0.2801 0.2822 0.242 Uiso 1 calc R . . H20C H 0.0553 0.2981 0.2690 0.242 Uiso 1 calc R . . C21 C 0.3748(3) 0.3531(4) 0.4761(3) 0.0770(12) Uani 1 d . . . H21A H 0.3609 0.4197 0.4283 0.092 Uiso 1 calc R . . H21B H 0.4507 0.3253 0.4948 0.092 Uiso 1 calc R . . C22 C 0.3563(3) 0.4093(4) 0.5578(3) 0.0866(13) Uani 1 d . . . H22A H 0.3737 0.3432 0.6063 0.104 Uiso 1 calc R . . H22B H 0.4062 0.4824 0.5821 0.104 Uiso 1 calc R . . C23 C 0.2248(4) 0.4681(5) 0.6227(3) 0.1168(17) Uani 1 d . . . H23A H 0.1510 0.4981 0.6085 0.175 Uiso 1 calc R . . H23B H 0.2755 0.5305 0.6626 0.175 Uiso 1 calc R . . H23C H 0.2348 0.3847 0.6537 0.175 Uiso 1 calc R . . C24 C 0.2222(4) 0.5768(5) 0.4848(4) 0.1292(19) Uani 1 d . . . H24A H 0.1476 0.6025 0.4720 0.194 Uiso 1 calc R . . H24B H 0.2330 0.5654 0.4272 0.194 Uiso 1 calc R . . H24C H 0.2711 0.6435 0.5213 0.194 Uiso 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 0.070(2) 0.0554(19) 0.094(2) -0.0200(18) 0.0465(18) -0.0104(17) N2 0.0554(17) 0.058(2) 0.080(2) -0.0133(17) 0.0347(15) -0.0021(16) N3 0.076(2) 0.079(3) 0.131(3) 0.015(2) 0.053(2) 0.015(2) N4 0.119(3) 0.071(3) 0.146(3) 0.028(2) 0.093(3) 0.020(2) N5 0.0598(19) 0.103(3) 0.086(2) 0.000(2) 0.0288(19) 0.004(2) N6 0.087(2) 0.059(2) 0.086(2) -0.0016(18) 0.042(2) 0.0154(18) C7 0.057(2) 0.045(2) 0.054(2) 0.0023(17) 0.0225(16) 0.0053(17) C8 0.061(2) 0.051(2) 0.062(2) 0.0035(18) 0.0273(18) -0.0004(18) C9 0.051(2) 0.045(2) 0.062(2) 0.0040(17) 0.0238(17) 0.0069(16) C10 0.0516(18) 0.044(2) 0.053(2) -0.0007(17) 0.0187(16) -0.0046(16) C11 0.065(2) 0.048(2) 0.074(3) 0.0061(19) 0.034(2) 0.0058(19) C12 0.062(2) 0.045(2) 0.065(2) 0.0048(19) 0.0227(19) 0.0095(18) C13 0.051(2) 0.056(2) 0.056(2) -0.0073(18) 0.0230(16) 0.0033(18) C14 0.053(2) 0.048(2) 0.066(2) 0.0040(19) 0.0258(18) -0.0011(17) C15 0.051(2) 0.063(3) 0.080(3) 0.002(2) 0.0304(19) -0.006(2) C16 0.070(2) 0.059(3) 0.088(3) -0.001(2) 0.043(2) 0.005(2) C17 0.084(3) 0.066(3) 0.140(4) -0.016(3) 0.076(3) -0.018(2) C18 0.059(3) 0.144(5) 0.123(4) -0.052(4) 0.040(3) -0.020(3) C19 0.094(3) 0.116(4) 0.130(4) -0.009(3) 0.065(3) 0.014(3) C20 0.096(4) 0.226(7) 0.154(5) 0.088(5) 0.038(4) 0.023(4) C21 0.073(3) 0.063(3) 0.103(3) -0.026(2) 0.042(2) -0.012(2) C22 0.094(3) 0.072(3) 0.088(3) -0.022(2) 0.027(3) -0.002(3) C23 0.165(5) 0.107(4) 0.106(4) -0.014(3) 0.083(4) 0.004(4) C24 0.166(5) 0.093(4) 0.144(5) 0.040(4) 0.075(4) 0.041(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 N1 C13 1.311(4) . ? N1 C17 1.458(4) . ? N2 C13 1.314(4) . ? N2 C21 1.464(4) . ? N3 C15 1.148(4) . ? N4 C16 1.146(5) . ? N5 C18 1.441(5) . ? N5 C19 1.447(5) . ? N5 C20 1.455(6) . ? N6 C22 1.446(4) . ? N6 C24 1.451(5) . ? N6 C23 1.464(4) . ? C7 C8 1.391(4) . ? C7 C12 1.390(4) . ? C7 C13 1.474(4) . ? C8 C9 1.371(4) . ? C9 C10 1.395(4) . ? C10 C11 1.404(4) . ? C10 C14 1.431(4) . ? C11 C12 1.369(4) . ? C14 C16 1.394(5) . ? C14 C15 1.401(5) . ? C17 C18 1.516(6) . ? C21 C22 1.487(5) . ? 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 C13 N1 C17 126.5(3) . . ? C13 N2 C21 126.9(3) . . ? C18 N5 C19 110.8(4) . . ? C18 N5 C20 112.5(4) . . ? C19 N5 C20 110.1(4) . . ? C22 N6 C24 112.5(4) . . ? C22 N6 C23 109.3(3) . . ? C24 N6 C23 110.3(4) . . ? C8 C7 C12 117.1(3) . . ? C8 C7 C13 121.0(3) . . ? C12 C7 C13 121.7(3) . . ? C9 C8 C7 121.4(3) . . ? C8 C9 C10 121.9(3) . . ? C9 C10 C11 116.3(3) . . ? C9 C10 C14 122.3(3) . . ? C11 C10 C14 121.4(3) . . ? C12 C11 C10 121.6(3) . . ? C11 C12 C7 121.6(3) . . ? N1 C13 N2 120.7(3) . . ? N1 C13 C7 117.2(3) . . ? N2 C13 C7 122.0(3) . . ? C16 C14 C15 117.7(3) . . ? C16 C14 C10 120.2(3) . . ? C15 C14 C10 122.1(3) . . ? N3 C15 C14 178.6(4) . . ? N4 C16 C14 177.5(4) . . ? N1 C17 C18 113.5(4) . . ? N5 C18 C17 111.0(4) . . ? N2 C21 C22 110.6(3) . . ? N6 C22 C21 113.4(3) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.11 _refine_diff_density_min -0.21 _refine_diff_density_rms 0.03 #------------------------------------------------------------------------ #===EOF #------------------------------------------------------------------------