# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 1999 # CCDC Number: 440/127 data_global _publ_contact_author_name 'Dr. Andres E. Goeta' _publ_contact_author_address ; Department of Chemistry Durham University Durham DH1 3LE UK ; _publ_contact_author_phone '+44 191 3744702' _publ_contact_author_fax '+44 191 3844737' _publ_contact_author_email A.E.Goeta@durham.ac.uk _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Crystal Structures of Amino substituted dicyanoquinodimethanes with Potential Nonlinear Optical Applications ; #============================================= data_2 _chemical_formula_sum 'C15 H14 N4' _chemical_formula_weight 250.30 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 orthorhombic _symmetry_space_group_name_H-M 'P 2(1) 2(1) 2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.803(1) _cell_length_b 9.474(1) _cell_length_c 17.819(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1317.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 492 _cell_measurement_theta_min 13.66 _cell_measurement_theta_max 26.75 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_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 'Bruker SMART-CCD' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10616 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3016 _reflns_number_gt 2346 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1999)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1999)' _computing_data_reduction 'SAINT-NT V5.0 (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Bruker, 1999)' _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^)+(0.0290P)^2^+0.3576P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 3016 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 N1 N 0.7634(3) 0.97536(16) 0.13200(9) 0.0295(4) Uani 1 1 d . . . N2 N 0.7690(3) 1.11648(18) 0.03431(10) 0.0381(5) Uani 1 1 d . . . H3N H 0.772(3) 1.145(2) -0.0156(13) 0.042(7) Uiso 1 1 d . . . N3 N 0.7693(3) 0.26923(19) -0.10296(10) 0.0450(5) Uani 1 1 d . . . N4 N 0.9043(3) 0.5540(2) -0.28842(11) 0.0489(6) Uani 1 1 d . . . C1 C 0.8477(3) 0.8751(2) 0.18395(12) 0.0345(5) Uani 1 1 d . . . H11B H 0.957(3) 0.833(3) 0.1598(13) 0.045(7) Uiso 1 1 d . . . H11A H 0.769(3) 0.799(2) 0.1967(12) 0.043(6) Uiso 1 1 d . . . C2 C 0.8911(4) 0.9668(2) 0.25278(14) 0.0386(6) Uani 1 1 d . . . H21A H 0.996(4) 0.940(3) 0.2780(14) 0.056(8) Uiso 1 1 d . . . H21B H 0.800(3) 0.958(2) 0.2934(14) 0.045(7) Uiso 1 1 d . . . C3 C 0.8945(3) 1.1189(2) 0.22292(12) 0.0330(5) Uani 1 1 d . . . H31A H 0.876(3) 1.192(3) 0.2634(13) 0.049(7) Uiso 1 1 d . . . H31B H 1.008(3) 1.141(2) 0.1963(13) 0.037(6) Uiso 1 1 d . . . C4 C 0.7502(3) 1.1196(2) 0.16556(11) 0.0305(4) Uani 1 1 d . . . H41 H 0.641(3) 1.128(2) 0.1931(11) 0.025(5) Uiso 1 1 d . . . C5 C 0.7607(4) 1.2176(2) 0.09696(13) 0.0415(6) Uani 1 1 d . . . H51A H 0.648(4) 1.279(3) 0.0929(15) 0.061(8) Uiso 1 1 d . . . H51B H 0.866(4) 1.277(3) 0.0957(14) 0.052(7) Uiso 1 1 d . . . C6 C 0.7792(3) 0.9832(2) 0.05756(11) 0.0300(5) Uani 1 1 d . . . C7 C 0.7999(3) 0.8651(2) 0.00653(11) 0.0278(4) Uani 1 1 d . . . C8 C 0.8514(3) 0.8877(2) -0.06834(11) 0.0295(5) Uani 1 1 d . . . H81 H 0.884(3) 0.986(2) -0.0850(12) 0.042(6) Uiso 1 1 d . . . C9 C 0.8640(3) 0.7771(2) -0.11814(11) 0.0292(5) Uani 1 1 d . . . H91 H 0.902(3) 0.794(2) -0.1695(11) 0.026(5) Uiso 1 1 d . . . C10 C 0.8229(2) 0.6369(2) -0.09635(12) 0.0262(4) Uani 1 1 d . . . C11 C 0.7743(3) 0.6156(2) -0.02108(11) 0.0306(5) Uani 1 1 d . . . H111 H 0.750(3) 0.520(2) -0.0051(11) 0.024(5) Uiso 1 1 d . . . C12 C 0.7628(3) 0.7264(2) 0.02919(11) 0.0307(5) Uani 1 1 d . . . H121 H 0.729(3) 0.706(2) 0.0838(13) 0.036(6) Uiso 1 1 d . . . C13 C 0.8291(3) 0.5212(2) -0.14941(11) 0.0295(5) Uani 1 1 d . . . C14 C 0.7974(3) 0.3820(2) -0.12451(11) 0.0329(5) Uani 1 1 d . . . C15 C 0.8702(3) 0.5399(2) -0.22556(12) 0.0337(5) Uani 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 0.0390(10) 0.0237(8) 0.0258(9) -0.0009(6) 0.0016(8) 0.0010(8) N2 0.0619(13) 0.0251(8) 0.0273(10) 0.0018(8) 0.0009(10) 0.0051(10) N3 0.0750(15) 0.0274(9) 0.0327(10) -0.0003(8) -0.0055(11) 0.0006(10) N4 0.0746(16) 0.0379(11) 0.0343(11) 0.0039(9) 0.0088(11) 0.0157(11) C1 0.0455(13) 0.0279(11) 0.0301(11) 0.0027(9) -0.0007(10) 0.0004(11) C2 0.0493(15) 0.0363(12) 0.0302(12) -0.0006(10) -0.0047(12) 0.0010(11) C3 0.0364(13) 0.0311(11) 0.0316(12) -0.0021(10) 0.0024(10) -0.0017(10) C4 0.0393(12) 0.0237(9) 0.0284(10) -0.0027(8) 0.0031(10) 0.0004(10) C5 0.0664(17) 0.0254(10) 0.0326(11) -0.0027(9) 0.0014(14) 0.0040(13) C6 0.0337(13) 0.0267(10) 0.0295(11) 0.0017(8) -0.0018(10) 0.0011(9) C7 0.0325(11) 0.0236(10) 0.0274(10) -0.0010(8) -0.0010(9) 0.0031(9) C8 0.0365(12) 0.0238(10) 0.0282(11) 0.0023(9) -0.0023(9) 0.0007(9) C9 0.0339(12) 0.0289(10) 0.0249(11) 0.0042(9) 0.0003(9) -0.0001(9) C10 0.0253(10) 0.0263(10) 0.0269(10) -0.0002(8) -0.0017(8) 0.0020(8) C11 0.0375(12) 0.0237(10) 0.0308(11) 0.0012(9) 0.0031(9) -0.0028(10) C12 0.0357(12) 0.0289(10) 0.0274(10) 0.0022(8) 0.0031(10) -0.0013(10) C13 0.0378(12) 0.0250(10) 0.0258(11) 0.0002(9) -0.0002(9) 0.0027(9) C14 0.0444(13) 0.0302(11) 0.0242(10) -0.0038(9) -0.0041(9) 0.0056(10) C15 0.0447(14) 0.0235(10) 0.0327(12) -0.0006(9) -0.0014(10) 0.0095(10) _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 C6 1.334(2) . ? N1 C1 1.480(3) . ? N1 C4 1.495(2) . ? N2 C6 1.331(3) . ? N2 C5 1.472(3) . ? N2 H3N 0.93(2) . ? N3 C14 1.156(3) . ? N4 C15 1.159(3) . ? C1 C2 1.541(3) . ? C1 H11B 1.03(3) . ? C1 H11A 0.97(2) . ? C2 C3 1.536(3) . ? C2 H21A 0.97(3) . ? C2 H21B 1.02(2) . ? C3 C4 1.521(3) . ? C3 H31A 1.01(2) . ? C3 H31B 1.03(2) . ? C4 C5 1.537(3) . ? C4 H41 0.99(2) . ? C5 H51A 1.06(3) . ? C5 H51B 1.00(3) . ? C6 C7 1.451(3) . ? C7 C12 1.405(3) . ? C7 C8 1.410(3) . ? C8 C9 1.377(3) . ? C8 H81 1.01(2) . ? C9 C10 1.421(3) . ? C9 H91 0.98(2) . ? C10 C11 1.408(3) . ? C10 C13 1.448(3) . ? C11 C12 1.383(3) . ? C11 H111 0.97(2) . ? C12 H121 1.03(2) . ? C13 C15 1.405(3) . ? C13 C14 1.413(3) . ? 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 C6 N1 C1 128.05(18) . . ? C6 N1 C4 110.68(16) . . ? C1 N1 C4 111.54(16) . . ? C6 N2 C5 112.57(18) . . ? C6 N2 H3N 124.8(14) . . ? C5 N2 H3N 122.6(14) . . ? N1 C1 C2 103.49(18) . . ? N1 C1 H11B 110.6(14) . . ? C2 C1 H11B 111.4(13) . . ? N1 C1 H11A 109.9(14) . . ? C2 C1 H11A 111.7(13) . . ? H11B C1 H11A 109.5(19) . . ? C3 C2 C1 104.90(19) . . ? C3 C2 H21A 113.0(16) . . ? C1 C2 H21A 114.1(15) . . ? C3 C2 H21B 109.9(13) . . ? C1 C2 H21B 111.3(14) . . ? H21A C2 H21B 104(2) . . ? C4 C3 C2 102.94(18) . . ? C4 C3 H31A 111.6(15) . . ? C2 C3 H31A 113.2(13) . . ? C4 C3 H31B 109.1(13) . . ? C2 C3 H31B 111.4(13) . . ? H31A C3 H31B 108.4(19) . . ? N1 C4 C3 102.34(17) . . ? N1 C4 C5 103.31(16) . . ? C3 C4 C5 119.8(2) . . ? N1 C4 H41 109.2(12) . . ? C3 C4 H41 107.8(12) . . ? C5 C4 H41 113.3(12) . . ? N2 C5 C4 102.25(16) . . ? N2 C5 H51A 110.1(15) . . ? C4 C5 H51A 110.1(15) . . ? N2 C5 H51B 108.4(15) . . ? C4 C5 H51B 113.8(15) . . ? H51A C5 H51B 111.7(18) . . ? N2 C6 N1 110.89(18) . . ? N2 C6 C7 122.89(19) . . ? N1 C6 C7 126.19(18) . . ? C12 C7 C8 118.21(19) . . ? C12 C7 C6 121.21(19) . . ? C8 C7 C6 120.53(18) . . ? C9 C8 C7 120.99(18) . . ? C9 C8 H81 119.6(13) . . ? C7 C8 H81 119.4(13) . . ? C8 C9 C10 121.29(19) . . ? C8 C9 H91 120.3(12) . . ? C10 C9 H91 118.4(12) . . ? C11 C10 C9 117.08(18) . . ? C11 C10 C13 121.49(18) . . ? C9 C10 C13 121.44(18) . . ? C12 C11 C10 121.71(19) . . ? C12 C11 H111 120.5(12) . . ? C10 C11 H111 117.7(12) . . ? C11 C12 C7 120.69(19) . . ? C11 C12 H121 119.2(12) . . ? C7 C12 H121 120.1(12) . . ? C15 C13 C14 117.43(18) . . ? C15 C13 C10 122.85(18) . . ? C14 C13 C10 119.70(18) . . ? N3 C14 C13 178.6(2) . . ? N4 C15 C13 179.4(2) . . ? 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 N1 C1 C2 141.1(2) . . . . ? C4 N1 C1 C2 -1.2(2) . . . . ? N1 C1 C2 C3 -22.1(2) . . . . ? C1 C2 C3 C4 36.9(2) . . . . ? C6 N1 C4 C3 -125.02(19) . . . . ? C1 N1 C4 C3 24.0(2) . . . . ? C6 N1 C4 C5 0.1(3) . . . . ? C1 N1 C4 C5 149.1(2) . . . . ? C2 C3 C4 N1 -36.5(2) . . . . ? C2 C3 C4 C5 -149.9(2) . . . . ? C6 N2 C5 C4 -5.3(3) . . . . ? N1 C4 C5 N2 2.9(3) . . . . ? C3 C4 C5 N2 115.8(2) . . . . ? C5 N2 C6 N1 5.7(3) . . . . ? C5 N2 C6 C7 -175.9(2) . . . . ? C1 N1 C6 N2 -146.0(2) . . . . ? C4 N1 C6 N2 -3.5(3) . . . . ? C1 N1 C6 C7 35.7(4) . . . . ? C4 N1 C6 C7 178.2(2) . . . . ? N2 C6 C7 C12 -162.0(2) . . . . ? N1 C6 C7 C12 16.2(3) . . . . ? N2 C6 C7 C8 15.5(3) . . . . ? N1 C6 C7 C8 -166.4(2) . . . . ? C12 C7 C8 C9 0.4(3) . . . . ? C6 C7 C8 C9 -177.1(2) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C8 C9 C10 C11 -2.1(3) . . . . ? C8 C9 C10 C13 177.4(2) . . . . ? C9 C10 C11 C12 1.6(3) . . . . ? C13 C10 C11 C12 -177.9(2) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C8 C7 C12 C11 -0.9(3) . . . . ? C6 C7 C12 C11 176.6(2) . . . . ? C11 C10 C13 C15 177.3(2) . . . . ? C9 C10 C13 C15 -2.1(3) . . . . ? C11 C10 C13 C14 -4.4(3) . . . . ? C9 C10 C13 C14 176.2(2) . . . . ? C15 C13 C14 N3 -153(10) . . . . ? C10 C13 C14 N3 29(10) . . . . ? C14 C13 C15 N4 -14(26) . . . . ? C10 C13 C15 N4 164(26) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H3N N3 0.93(2) 1.95(2) 2.842(2) 160(2) 1_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.141 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.044 #===END data_4 _chemical_formula_sum 'C18 H16 F4 N4' _chemical_formula_weight 364.35 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' 'F' 'F' 0.0171 0.0103 '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 '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 10.114(1) _cell_length_b 14.412(2) _cell_length_c 12.142(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.634(6) _cell_angle_gamma 90.00 _cell_volume 1621.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 192 _cell_measurement_theta_min 13.64 _cell_measurement_theta_max 21.39 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_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 'Bruker SMART-CCD' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10751 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3715 _reflns_number_gt 2397 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SAINT-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Bruker, 1998)' _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^)+(0.0358P)^2^+1.0466P] 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 3715 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1011 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1208 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.48261(15) -0.10425(9) 1.32249(12) 0.0296(3) Uani 1 1 d . . . F2 F 0.48984(15) -0.13046(9) 1.10997(12) 0.0299(3) Uani 1 1 d . . . F3 F 0.08836(14) 0.07296(9) 0.93636(11) 0.0266(3) Uani 1 1 d . . . F4 F 0.08538(15) 0.09878(9) 1.14922(11) 0.0280(3) Uani 1 1 d . . . N1 N 0.2373(2) -0.07362(12) 1.40459(16) 0.0219(4) Uani 1 1 d . . . N2 N 0.2770(2) 0.08667(13) 1.41291(17) 0.0232(4) Uani 1 1 d . . . N3 N 0.4616(3) -0.15296(16) 0.8430(2) 0.0417(6) Uani 1 1 d . . . N4 N 0.1002(3) 0.02353(16) 0.6977(2) 0.0385(6) Uani 1 1 d . . . C1 C 0.3419(3) 0.17029(16) 1.3825(3) 0.0277(6) Uani 1 1 d . . . C2 C 0.2443(3) 0.24724(18) 1.3884(3) 0.0377(7) Uani 1 1 d . . . C3 C 0.2046(4) 0.21999(19) 1.4903(3) 0.0443(8) Uani 1 1 d . . . C4 C 0.1975(3) 0.11449(17) 1.4881(2) 0.0259(5) Uani 1 1 d . . . C5 C 0.2666(2) 0.00409(15) 1.3602(2) 0.0211(5) Uani 1 1 d . . . C6 C 0.2467(3) -0.08784(17) 1.5287(2) 0.0271(5) Uani 1 1 d . . . C7 C 0.2320(3) -0.19267(17) 1.5363(2) 0.0309(6) Uani 1 1 d . . . C8 C 0.1297(3) -0.21815(18) 1.4084(2) 0.0300(6) Uani 1 1 d . . . C9 C 0.1849(3) -0.15981(16) 1.3313(2) 0.0273(6) Uani 1 1 d . . . C10 C 0.2831(3) -0.00267(15) 1.2445(2) 0.0220(5) Uani 1 1 d . . . C11 C 0.3833(2) -0.06002(15) 1.2268(2) 0.0221(5) Uani 1 1 d . . . C12 C 0.3860(2) -0.07339(15) 1.1157(2) 0.0212(5) Uani 1 1 d . . . C13 C 0.2887(2) -0.03131(15) 1.0098(2) 0.0211(5) Uani 1 1 d . . . C14 C 0.1891(2) 0.02772(15) 1.0304(2) 0.0205(5) Uani 1 1 d . . . C15 C 0.1879(2) 0.04161(15) 1.1414(2) 0.0216(5) Uani 1 1 d . . . C16 C 0.2879(3) -0.04686(16) 0.8926(2) 0.0237(5) Uani 1 1 d . . . C17 C 0.3866(3) -0.10583(17) 0.8701(2) 0.0273(5) Uani 1 1 d . . . C18 C 0.1833(3) -0.00667(17) 0.7873(2) 0.0272(5) Uani 1 1 d . . . H11 H 0.443(3) 0.1795(18) 1.445(2) 0.045(8) Uiso 1 1 d . . . H12 H 0.352(3) 0.1632(17) 1.307(2) 0.033(7) Uiso 1 1 d . . . H21 H 0.282(3) 0.3077(18) 1.393(2) 0.030(7) Uiso 1 1 d . . . H22 H 0.149(4) 0.246(2) 1.306(3) 0.071(11) Uiso 1 1 d . . . H31 H 0.293(4) 0.244(3) 1.574(3) 0.091(13) Uiso 1 1 d . . . H32 H 0.117(4) 0.245(2) 1.486(3) 0.060(10) Uiso 1 1 d . . . H41 H 0.102(3) 0.0899(16) 1.451(2) 0.026(7) Uiso 1 1 d . . . H42 H 0.245(3) 0.0889(16) 1.572(2) 0.028(7) Uiso 1 1 d . . . H61 H 0.164(3) -0.0560(17) 1.539(2) 0.033(7) Uiso 1 1 d . . . H62 H 0.341(3) -0.0617(16) 1.587(2) 0.027(7) Uiso 1 1 d . . . H71 H 0.194(3) -0.2094(18) 1.599(2) 0.043(8) Uiso 1 1 d . . . H72 H 0.329(3) -0.2228(17) 1.556(2) 0.032(7) Uiso 1 1 d . . . H81 H 0.030(3) -0.1986(16) 1.393(2) 0.025(6) Uiso 1 1 d . . . H82 H 0.132(3) -0.2832(18) 1.388(2) 0.028(7) Uiso 1 1 d . . . H91 H 0.112(3) -0.1437(17) 1.253(2) 0.030(7) Uiso 1 1 d . . . H92 H 0.267(3) -0.1921(17) 1.320(2) 0.033(7) 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 F1 0.0263(8) 0.0336(8) 0.0272(7) 0.0051(6) 0.0090(6) 0.0081(6) F2 0.0276(8) 0.0315(8) 0.0353(8) 0.0008(6) 0.0174(7) 0.0088(6) F3 0.0301(8) 0.0256(7) 0.0247(7) 0.0046(6) 0.0116(6) 0.0058(6) F4 0.0306(8) 0.0261(8) 0.0320(8) 0.0031(6) 0.0174(7) 0.0094(6) N1 0.0240(10) 0.0196(10) 0.0226(10) 0.0009(8) 0.0099(9) 0.0002(8) N2 0.0283(11) 0.0192(10) 0.0279(11) -0.0001(8) 0.0174(9) -0.0021(8) N3 0.0435(15) 0.0458(15) 0.0409(14) -0.0081(11) 0.0222(12) 0.0061(12) N4 0.0410(14) 0.0516(15) 0.0272(12) 0.0009(11) 0.0180(11) 0.0074(11) C1 0.0328(15) 0.0209(13) 0.0368(15) 0.0002(11) 0.0218(13) -0.0046(11) C2 0.0431(17) 0.0207(14) 0.062(2) 0.0030(13) 0.0344(16) -0.0010(12) C3 0.057(2) 0.0264(15) 0.070(2) -0.0027(14) 0.0468(19) -0.0007(14) C4 0.0292(14) 0.0240(13) 0.0321(14) -0.0028(11) 0.0201(12) -0.0033(11) C5 0.0187(12) 0.0222(12) 0.0227(12) 0.0006(9) 0.0085(10) 0.0021(9) C6 0.0354(15) 0.0240(13) 0.0239(13) 0.0018(10) 0.0139(12) -0.0022(11) C7 0.0364(16) 0.0247(14) 0.0340(15) 0.0069(11) 0.0167(13) -0.0004(11) C8 0.0311(15) 0.0190(13) 0.0421(16) 0.0008(11) 0.0169(13) -0.0026(11) C9 0.0336(15) 0.0189(12) 0.0300(14) -0.0032(10) 0.0132(12) -0.0030(11) C10 0.0246(13) 0.0206(12) 0.0228(12) 0.0006(9) 0.0117(10) 0.0007(10) C11 0.0207(12) 0.0219(12) 0.0227(12) 0.0028(9) 0.0076(10) 0.0005(9) C12 0.0200(12) 0.0161(11) 0.0317(13) -0.0018(9) 0.0148(10) 0.0006(9) C13 0.0231(12) 0.0171(11) 0.0256(12) -0.0014(9) 0.0124(10) -0.0036(9) C14 0.0225(12) 0.0177(12) 0.0221(12) 0.0038(9) 0.0099(10) 0.0000(9) C15 0.0216(12) 0.0165(11) 0.0320(13) 0.0000(9) 0.0162(10) 0.0026(9) C16 0.0256(13) 0.0235(12) 0.0246(12) -0.0003(10) 0.0128(10) -0.0023(10) C17 0.0293(14) 0.0299(14) 0.0254(13) -0.0037(10) 0.0139(11) -0.0034(11) C18 0.0322(14) 0.0293(14) 0.0270(13) -0.0053(11) 0.0191(12) -0.0021(11) _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 C11 1.353(3) . ? F2 C12 1.357(2) . ? F3 C14 1.354(2) . ? F4 C15 1.357(2) . ? N1 C5 1.327(3) . ? N1 C6 1.486(3) . ? N1 C9 1.496(3) . ? N2 C5 1.335(3) . ? N2 C1 1.488(3) . ? N2 C4 1.494(3) . ? N3 C17 1.160(3) . ? N4 C18 1.160(3) . ? C1 C2 1.506(4) . ? C1 H11 1.01(3) . ? C1 H12 0.97(3) . ? C2 C3 1.498(4) . ? C2 H21 0.94(3) . ? C2 H22 1.08(3) . ? C3 C4 1.522(4) . ? C3 H31 1.11(4) . ? C3 H32 0.94(4) . ? C4 H41 0.96(3) . ? C4 H42 1.01(2) . ? C5 C10 1.482(3) . ? C6 C7 1.525(3) . ? C6 H61 1.00(3) . ? C6 H62 1.01(3) . ? C7 C8 1.526(4) . ? C7 H71 1.01(3) . ? C7 H72 1.01(3) . ? C8 C9 1.521(4) . ? C8 H81 0.99(3) . ? C8 H82 0.97(3) . ? C9 H91 0.97(3) . ? C9 H92 1.01(3) . ? C10 C11 1.390(3) . ? C10 C15 1.391(3) . ? C11 C12 1.374(3) . ? C12 C13 1.406(3) . ? C13 C14 1.415(3) . ? C13 C16 1.437(3) . ? C14 C15 1.368(3) . ? C16 C18 1.416(3) . ? C16 C17 1.418(3) . ? 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 C5 N1 C6 126.48(19) . . ? C5 N1 C9 122.87(19) . . ? C6 N1 C9 110.62(18) . . ? C5 N2 C1 124.09(19) . . ? C5 N2 C4 125.04(19) . . ? C1 N2 C4 109.50(18) . . ? N2 C1 C2 102.8(2) . . ? N2 C1 H11 109.3(16) . . ? C2 C1 H11 110.5(16) . . ? N2 C1 H12 112.0(15) . . ? C2 C1 H12 116.3(15) . . ? H11 C1 H12 106(2) . . ? C3 C2 C1 104.1(2) . . ? C3 C2 H21 115.2(15) . . ? C1 C2 H21 115.3(16) . . ? C3 C2 H22 109.3(19) . . ? C1 C2 H22 107.1(18) . . ? H21 C2 H22 106(2) . . ? C2 C3 C4 105.9(2) . . ? C2 C3 H31 107(2) . . ? C4 C3 H31 110.1(19) . . ? C2 C3 H32 115(2) . . ? C4 C3 H32 110(2) . . ? H31 C3 H32 109(3) . . ? N2 C4 C3 104.2(2) . . ? N2 C4 H41 107.3(14) . . ? C3 C4 H41 114.3(14) . . ? N2 C4 H42 111.3(14) . . ? C3 C4 H42 110.3(14) . . ? H41 C4 H42 109(2) . . ? N1 C5 N2 123.0(2) . . ? N1 C5 C10 117.23(19) . . ? N2 C5 C10 119.71(19) . . ? N1 C6 C7 103.31(19) . . ? N1 C6 H61 110.1(14) . . ? C7 C6 H61 109.8(15) . . ? N1 C6 H62 108.8(14) . . ? C7 C6 H62 114.5(13) . . ? H61 C6 H62 110(2) . . ? C6 C7 C8 102.7(2) . . ? C6 C7 H71 111.1(15) . . ? C8 C7 H71 113.8(16) . . ? C6 C7 H72 109.3(15) . . ? C8 C7 H72 109.5(14) . . ? H71 C7 H72 110(2) . . ? C9 C8 C7 103.1(2) . . ? C9 C8 H81 108.8(14) . . ? C7 C8 H81 110.3(14) . . ? C9 C8 H82 109.3(14) . . ? C7 C8 H82 114.4(14) . . ? H81 C8 H82 110(2) . . ? N1 C9 C8 102.87(19) . . ? N1 C9 H91 109.6(15) . . ? C8 C9 H91 114.8(15) . . ? N1 C9 H92 110.4(15) . . ? C8 C9 H92 110.9(14) . . ? H91 C9 H92 108(2) . . ? C11 C10 C15 114.7(2) . . ? C11 C10 C5 123.5(2) . . ? C15 C10 C5 121.5(2) . . ? F1 C11 C12 118.5(2) . . ? F1 C11 C10 119.0(2) . . ? C12 C11 C10 122.6(2) . . ? F2 C12 C11 117.1(2) . . ? F2 C12 C13 119.11(19) . . ? C11 C12 C13 123.7(2) . . ? C12 C13 C14 112.6(2) . . ? C12 C13 C16 124.2(2) . . ? C14 C13 C16 123.1(2) . . ? F3 C14 C15 117.4(2) . . ? F3 C14 C13 119.26(19) . . ? C15 C14 C13 123.4(2) . . ? F4 C15 C14 117.8(2) . . ? F4 C15 C10 119.2(2) . . ? C14 C15 C10 123.0(2) . . ? C18 C16 C17 113.6(2) . . ? C18 C16 C13 122.4(2) . . ? C17 C16 C13 124.0(2) . . ? N3 C17 C16 175.1(3) . . ? N4 C18 C16 176.6(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 C5 N2 C1 C2 141.0(2) . . . . ? C4 N2 C1 C2 -26.1(3) . . . . ? N2 C1 C2 C3 36.3(3) . . . . ? C1 C2 C3 C4 -33.7(3) . . . . ? C5 N2 C4 C3 -161.3(2) . . . . ? C1 N2 C4 C3 5.7(3) . . . . ? C2 C3 C4 N2 17.3(3) . . . . ? C6 N1 C5 N2 -16.0(4) . . . . ? C9 N1 C5 N2 162.2(2) . . . . ? C6 N1 C5 C10 166.2(2) . . . . ? C9 N1 C5 C10 -15.7(3) . . . . ? C1 N2 C5 N1 165.3(2) . . . . ? C4 N2 C5 N1 -29.5(4) . . . . ? C1 N2 C5 C10 -16.9(3) . . . . ? C4 N2 C5 C10 148.3(2) . . . . ? C5 N1 C6 C7 -168.7(2) . . . . ? C9 N1 C6 C7 12.9(3) . . . . ? N1 C6 C7 C8 -33.5(3) . . . . ? C6 C7 C8 C9 42.2(3) . . . . ? C5 N1 C9 C8 -165.4(2) . . . . ? C6 N1 C9 C8 13.0(3) . . . . ? C7 C8 C9 N1 -33.7(3) . . . . ? N1 C5 C10 C11 -57.7(3) . . . . ? N2 C5 C10 C11 124.3(2) . . . . ? N1 C5 C10 C15 115.6(2) . . . . ? N2 C5 C10 C15 -62.3(3) . . . . ? C15 C10 C11 F1 178.4(2) . . . . ? C5 C10 C11 F1 -7.9(3) . . . . ? C15 C10 C11 C12 -1.3(3) . . . . ? C5 C10 C11 C12 172.4(2) . . . . ? F1 C11 C12 F2 -0.2(3) . . . . ? C10 C11 C12 F2 179.5(2) . . . . ? F1 C11 C12 C13 -180.0(2) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? F2 C12 C13 C14 -178.65(19) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? F2 C12 C13 C16 2.2(3) . . . . ? C11 C12 C13 C16 -178.1(2) . . . . ? C12 C13 C14 F3 -179.86(19) . . . . ? C16 C13 C14 F3 -0.7(3) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C16 C13 C14 C15 178.9(2) . . . . ? F3 C14 C15 F4 0.7(3) . . . . ? C13 C14 C15 F4 -178.9(2) . . . . ? F3 C14 C15 C10 178.2(2) . . . . ? C13 C14 C15 C10 -1.4(4) . . . . ? C11 C10 C15 F4 179.6(2) . . . . ? C5 C10 C15 F4 5.8(3) . . . . ? C11 C10 C15 C14 2.1(3) . . . . ? C5 C10 C15 C14 -171.7(2) . . . . ? C12 C13 C16 C18 176.7(2) . . . . ? C14 C13 C16 C18 -2.4(4) . . . . ? C12 C13 C16 C17 -0.8(4) . . . . ? C14 C13 C16 C17 -179.9(2) . . . . ? C18 C16 C17 N3 -4(3) . . . . ? C13 C16 C17 N3 174(3) . . . . ? C17 C16 C18 N4 6(5) . . . . ? C13 C16 C18 N4 -171(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.411 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.057 #===END