# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2011 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _publ_contact_author_name 'Regis Goumont' _publ_contact_author_address ; ; _publ_contact_author_email goumont@chimie.uvsq.fr loop_ _publ_author_name R.Goumont A.-M.Goncalves T.Devic C.Mathieu G.Berionni ; A.Etcheberry ; data_sad _database_code_depnum_ccdc_archive 'CCDC 741714' #TrackingRef '- Cif Files.txt' #TrackingRef '- Cif Files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetrathiafulvalene, 6,cyano-4,nitrobenzofuroxane ; _chemical_name_common 'tetrathiafulvalene, 6,cyano-4,nitrobenzofuroxane' _chemical_melting_point ? _chemical_formula_moiety C104H48N32O32S32 _chemical_formula_sum 'C104 H48 N32 O32 S32' _chemical_formula_weight 3283.66 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' S S 0.1246 0.1234 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8201(12) _cell_length_b 16.9483(16) _cell_length_c 14.7822(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.024(2) _cell_angle_gamma 90.00 _cell_volume 3211.9(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6911 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 28.38 _exptl_crystal_description parallelepiped _exptl_crystal_colour black _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8358 _exptl_absorpt_correction_T_max 0.9637 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21897 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0782 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.38 _reflns_number_total 7998 _reflns_number_gt 5344 _reflns_threshold_expression >2sigma(I) _computing_data_collection SAINT _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0712P)^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 7998 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1382 _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.1790 _refine_ls_wR_factor_gt 0.1645 _refine_ls_goodness_of_fit_ref 1.239 _refine_ls_restrained_S_all 1.239 _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 S1 S 0.79808(8) 0.14261(6) 0.33111(8) 0.0362(3) Uani 1 1 d . . . S2 S 0.57178(8) 0.16482(6) 0.36364(8) 0.0373(3) Uani 1 1 d . . . S13 S 0.30792(8) 0.42632(6) 0.36513(8) 0.0393(3) Uani 1 1 d . . . S14 S 0.08338(8) 0.40382(7) 0.40310(9) 0.0454(3) Uani 1 1 d . . . S4 S 0.59785(8) 0.35126(6) 0.30787(9) 0.0464(3) Uani 1 1 d . . . S12 S 0.10071(8) 0.22372(6) 0.31791(9) 0.0465(3) Uani 1 1 d . . . S3 S 0.82061(8) 0.32270(6) 0.27142(8) 0.0421(3) Uani 1 1 d . . . S11 S 0.32623(8) 0.25116(6) 0.28869(8) 0.0422(3) Uani 1 1 d . . . O3 O 0.5151(2) 0.21789(18) 0.1374(2) 0.0514(8) Uani 1 1 d . . . C03 C 0.6847(3) 0.1910(2) 0.0986(3) 0.0299(9) Uani 1 1 d . . . N2 N 0.6383(2) 0.32906(19) 0.0535(3) 0.0402(9) Uani 1 1 d . . . O6 O 0.6959(2) 0.30283(15) 0.5372(2) 0.0443(8) Uani 1 1 d . . . N5 N 0.8000(3) 0.27429(19) 0.5253(2) 0.0367(8) Uani 1 1 d . . . N7 N 0.5812(2) 0.0836(2) 0.6595(3) 0.0408(9) Uani 1 1 d . . . N1 N 0.8035(2) 0.36041(18) 0.0040(2) 0.0333(8) Uani 1 1 d . . . C06 C 0.8890(3) 0.2338(2) 0.0391(3) 0.0335(9) Uani 1 1 d . . . H06 H 0.9553 0.2478 0.0191 0.040 Uiso 1 1 calc R . . C010 C 0.6841(3) 0.1081(2) 0.6283(3) 0.0314(9) Uani 1 1 d . . . O2 O 0.8677(2) 0.40557(16) -0.0283(2) 0.0518(8) Uani 1 1 d . . . C09 C 0.7005(3) 0.1845(2) 0.5900(3) 0.0275(8) Uani 1 1 d . . . C02 C 0.7022(3) 0.2685(2) 0.0635(3) 0.0279(8) Uani 1 1 d . . . O1 O 0.6979(2) 0.38846(15) 0.0158(2) 0.0429(7) Uani 1 1 d . . . N6 N 0.6362(2) 0.24444(19) 0.5787(2) 0.0403(9) Uani 1 1 d . . . C01 C 0.8039(3) 0.2858(2) 0.0348(3) 0.0286(8) Uani 1 1 d . . . O8 O 0.5723(2) 0.01971(19) 0.6959(3) 0.0600(9) Uani 1 1 d . . . O5 O 0.8641(3) 0.31737(18) 0.4902(2) 0.0599(9) Uani 1 1 d . . . C08 C 0.8009(3) 0.2004(2) 0.5576(3) 0.0291(9) Uani 1 1 d . . . C14 C 0.1990(3) 0.3633(2) 0.3602(3) 0.0340(9) Uani 1 1 d . . . O7 O 0.5096(2) 0.1292(2) 0.6461(3) 0.0731(12) Uani 1 1 d . . . C013 C 0.8850(3) 0.1484(2) 0.5613(3) 0.0323(9) Uani 1 1 d . . . H013 H 0.9501 0.1614 0.5380 0.039 Uiso 1 1 calc R . . C011 C 0.7655(3) 0.0572(2) 0.6342(3) 0.0313(9) Uani 1 1 d . . . H011 H 0.7551 0.0079 0.6604 0.038 Uiso 1 1 calc R . . C05 C 0.8679(3) 0.1613(2) 0.0746(3) 0.0321(9) Uani 1 1 d . . . N3 N 0.5816(2) 0.1667(2) 0.1305(2) 0.0357(8) Uani 1 1 d . . . O4 O 0.5691(2) 0.09743(18) 0.1504(2) 0.0580(9) Uani 1 1 d . . . C04 C 0.7648(3) 0.1399(2) 0.1039(3) 0.0322(9) Uani 1 1 d . . . H04 H 0.7533 0.0896 0.1270 0.039 Uiso 1 1 calc R . . C4 C 0.7007(3) 0.2837(2) 0.3058(3) 0.0298(9) Uani 1 1 d . . . C13 C 0.2061(3) 0.2895(2) 0.3265(3) 0.0318(9) Uani 1 1 d . . . C012 C 0.8660(3) 0.0770(2) 0.6013(3) 0.0307(9) Uani 1 1 d . . . C3 C 0.6907(3) 0.2073(2) 0.3294(3) 0.0295(9) Uani 1 1 d . . . C11 C 0.2763(4) 0.1609(3) 0.2566(3) 0.0512(12) Uani 1 1 d . . . H11 H 0.3185 0.1222 0.2312 0.061 Uiso 1 1 calc R . . N4 N 1.0132(3) 0.0593(2) 0.1007(4) 0.0743(15) Uani 1 1 d . . . C15 C 0.2424(4) 0.4994(2) 0.4245(3) 0.0512(12) Uani 1 1 d . . . H15 H 0.2771 0.5441 0.4452 0.061 Uiso 1 1 calc R . . C1 C 0.7310(3) 0.0683(2) 0.3873(3) 0.0416(11) Uani 1 1 d . . . H1 H 0.7649 0.0228 0.4066 0.050 Uiso 1 1 calc R . . N8 N 1.0144(3) -0.0245(2) 0.6214(3) 0.0670(13) Uani 1 1 d . . . C12 C 0.1752(4) 0.1489(3) 0.2698(3) 0.0558(13) Uani 1 1 d . . . H12 H 0.1446 0.1012 0.2536 0.067 Uiso 1 1 calc R . . C014 C 0.9496(3) 0.0200(2) 0.6114(3) 0.0428(11) Uani 1 1 d . . . C07 C 0.9502(3) 0.1044(2) 0.0874(3) 0.0464(12) Uani 1 1 d . . . C2 C 0.6299(3) 0.0785(2) 0.4017(3) 0.0415(10) Uani 1 1 d . . . H2 H 0.5909 0.0403 0.4316 0.050 Uiso 1 1 calc R . . C16 C 0.1423(4) 0.4896(3) 0.4393(4) 0.0556(13) Uani 1 1 d . . . H16 H 0.1038 0.5283 0.4688 0.067 Uiso 1 1 calc R . . C6 C 0.6779(4) 0.4315(3) 0.2852(4) 0.0607(15) Uani 1 1 d . . . H6 H 0.6508 0.4824 0.2842 0.073 Uiso 1 1 calc R . . C5 C 0.7771(4) 0.4193(3) 0.2695(4) 0.0588(14) Uani 1 1 d . . . H5 H 0.8224 0.4610 0.2578 0.071 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 S1 0.0354(5) 0.0341(5) 0.0391(7) 0.0012(5) 0.0015(5) 0.0110(4) S2 0.0329(5) 0.0377(6) 0.0413(7) 0.0048(5) 0.0045(5) -0.0010(4) S13 0.0325(5) 0.0382(6) 0.0472(7) 0.0034(5) 0.0033(5) -0.0049(4) S14 0.0325(5) 0.0494(7) 0.0543(8) 0.0001(6) 0.0108(5) 0.0027(5) S4 0.0422(6) 0.0332(6) 0.0638(9) 0.0024(5) 0.0034(6) 0.0121(5) S12 0.0431(6) 0.0440(6) 0.0523(8) 0.0046(6) -0.0008(5) -0.0116(5) S3 0.0372(6) 0.0455(6) 0.0437(7) 0.0062(5) 0.0037(5) -0.0060(5) S11 0.0376(6) 0.0437(6) 0.0454(7) 0.0010(5) 0.0021(5) 0.0079(5) O3 0.0280(15) 0.066(2) 0.060(2) 0.0140(17) 0.0061(15) 0.0088(14) C03 0.0264(19) 0.036(2) 0.027(2) -0.0040(17) -0.0004(16) -0.0030(16) N2 0.0297(17) 0.0389(19) 0.052(3) 0.0060(17) 0.0020(16) 0.0056(15) O6 0.0478(17) 0.0322(15) 0.053(2) 0.0003(14) -0.0047(15) 0.0092(13) N5 0.0404(19) 0.0343(18) 0.035(2) -0.0038(16) -0.0020(16) -0.0066(16) N7 0.0333(19) 0.047(2) 0.042(2) -0.0084(18) 0.0043(17) -0.0058(16) N1 0.0334(18) 0.0283(17) 0.038(2) -0.0028(15) 0.0044(15) -0.0016(14) C06 0.0223(18) 0.040(2) 0.038(3) -0.0090(19) 0.0022(17) 0.0010(16) C010 0.0274(19) 0.035(2) 0.032(2) -0.0091(18) -0.0003(17) -0.0041(16) O2 0.0492(18) 0.0388(17) 0.067(2) 0.0084(16) 0.0117(17) -0.0087(14) C09 0.0252(18) 0.0300(19) 0.027(2) -0.0094(16) -0.0035(16) 0.0021(15) C02 0.0231(18) 0.035(2) 0.026(2) -0.0023(17) -0.0001(15) 0.0039(15) O1 0.0355(15) 0.0331(15) 0.060(2) 0.0084(14) 0.0053(14) 0.0068(12) N6 0.0323(18) 0.0372(19) 0.051(2) -0.0047(17) -0.0061(17) 0.0069(15) C01 0.0276(19) 0.030(2) 0.028(2) -0.0030(17) 0.0007(16) -0.0017(15) O8 0.0512(19) 0.055(2) 0.074(3) 0.0016(19) 0.0146(18) -0.0166(16) O5 0.068(2) 0.0488(19) 0.063(3) 0.0073(17) 0.0006(19) -0.0134(17) C08 0.0309(19) 0.0280(19) 0.028(2) -0.0058(16) -0.0010(17) -0.0008(15) C14 0.028(2) 0.038(2) 0.035(3) 0.0088(18) 0.0040(17) -0.0025(16) O7 0.0290(17) 0.089(3) 0.102(3) 0.020(2) 0.0137(18) 0.0145(17) C013 0.0201(18) 0.041(2) 0.036(2) -0.0072(19) -0.0003(17) -0.0009(16) C011 0.034(2) 0.0263(19) 0.033(2) -0.0037(17) -0.0025(18) -0.0030(16) C05 0.0264(19) 0.033(2) 0.037(3) -0.0043(18) -0.0030(17) 0.0046(16) N3 0.0272(17) 0.048(2) 0.032(2) 0.0061(17) -0.0003(15) -0.0045(15) O4 0.0541(19) 0.0494(19) 0.071(3) 0.0161(17) 0.0122(18) -0.0124(15) C04 0.033(2) 0.0286(19) 0.035(2) 0.0005(17) -0.0008(18) -0.0018(16) C4 0.0302(19) 0.0285(19) 0.031(2) -0.0029(17) 0.0034(17) 0.0051(15) C13 0.030(2) 0.031(2) 0.034(2) 0.0078(18) 0.0028(17) 0.0005(16) C012 0.0228(18) 0.032(2) 0.038(2) -0.0020(18) -0.0010(17) 0.0043(15) C3 0.0287(19) 0.031(2) 0.028(2) 0.0000(17) 0.0048(17) 0.0043(15) C11 0.069(3) 0.039(2) 0.046(3) -0.002(2) -0.008(3) 0.012(2) N4 0.047(2) 0.054(3) 0.122(5) 0.010(3) -0.001(3) 0.017(2) C15 0.058(3) 0.032(2) 0.064(4) -0.005(2) 0.011(3) -0.007(2) C1 0.060(3) 0.025(2) 0.039(3) -0.0001(18) -0.011(2) 0.0043(19) N8 0.042(2) 0.056(2) 0.103(4) 0.003(3) 0.001(2) 0.0202(19) C12 0.083(4) 0.032(2) 0.052(3) 0.001(2) -0.014(3) -0.004(2) C014 0.029(2) 0.042(2) 0.057(3) 0.001(2) -0.002(2) 0.0031(18) C07 0.035(2) 0.039(2) 0.066(4) 0.000(2) 0.002(2) 0.0028(19) C2 0.059(3) 0.027(2) 0.039(3) 0.0046(19) -0.006(2) -0.0076(19) C16 0.060(3) 0.036(2) 0.071(4) -0.006(2) 0.020(3) 0.008(2) C6 0.075(4) 0.028(2) 0.079(4) 0.001(2) -0.012(3) 0.000(2) C5 0.067(3) 0.034(2) 0.076(4) 0.017(2) -0.013(3) -0.015(2) _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 S1 C1 1.737(4) . ? S1 C3 1.760(4) . ? S2 C2 1.735(4) . ? S2 C3 1.760(4) . ? S13 C15 1.735(4) . ? S13 C14 1.760(4) . ? S14 C16 1.723(5) . ? S14 C14 1.752(4) . ? S4 C6 1.737(5) . ? S4 C4 1.746(4) . ? S12 C12 1.739(5) . ? S12 C13 1.757(4) . ? S3 C5 1.730(5) . ? S3 C4 1.749(4) . ? S11 C11 1.725(5) . ? S11 C13 1.762(4) . ? O3 N3 1.220(4) . ? C03 C04 1.346(5) . ? C03 C02 1.430(5) . ? C03 N3 1.463(5) . ? N2 C02 1.322(4) . ? N2 O1 1.381(4) . ? O6 N6 1.394(4) . ? O6 N5 1.431(4) . ? N5 O5 1.215(4) . ? N5 C08 1.340(5) . ? N7 O7 1.215(4) . ? N7 O8 1.214(4) . ? N7 C010 1.457(5) . ? N1 O2 1.221(4) . ? N1 C01 1.344(5) . ? N1 O1 1.446(4) . ? C06 C05 1.362(5) . ? C06 C01 1.404(5) . ? C06 H06 0.9300 . ? C010 C011 1.357(5) . ? C010 C09 1.429(5) . ? C09 N6 1.319(4) . ? C09 C08 1.400(5) . ? C02 C01 1.402(5) . ? C08 C013 1.393(5) . ? C14 C13 1.349(5) . ? C013 C012 1.368(5) . ? C013 H013 0.9300 . ? C011 C012 1.417(5) . ? C011 H011 0.9300 . ? C05 C04 1.437(5) . ? C05 C07 1.443(5) . ? N3 O4 1.221(4) . ? C04 H04 0.9300 . ? C4 C3 1.348(5) . ? C012 C014 1.451(5) . ? C11 C12 1.326(6) . ? C11 H11 0.9300 . ? N4 C07 1.128(5) . ? C15 C16 1.313(6) . ? C15 H15 0.9300 . ? C1 C2 1.325(6) . ? C1 H1 0.9300 . ? N8 C014 1.132(5) . ? C12 H12 0.9300 . ? C2 H2 0.9300 . ? C16 H16 0.9300 . ? C6 C5 1.309(6) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C3 94.06(19) . . ? C2 S2 C3 93.78(19) . . ? C15 S13 C14 94.0(2) . . ? C16 S14 C14 94.1(2) . . ? C6 S4 C4 93.6(2) . . ? C12 S12 C13 94.0(2) . . ? C5 S3 C4 94.5(2) . . ? C11 S11 C13 95.2(2) . . ? C04 C03 C02 119.5(3) . . ? C04 C03 N3 119.4(3) . . ? C02 C03 N3 121.2(3) . . ? C02 N2 O1 105.6(3) . . ? N6 O6 N5 109.1(3) . . ? O5 N5 C08 135.1(4) . . ? O5 N5 O6 118.7(3) . . ? C08 N5 O6 106.2(3) . . ? O7 N7 O8 124.6(4) . . ? O7 N7 C010 116.8(4) . . ? O8 N7 C010 118.6(3) . . ? O2 N1 C01 136.0(3) . . ? O2 N1 O1 118.2(3) . . ? C01 N1 O1 105.8(3) . . ? C05 C06 C01 115.3(3) . . ? C05 C06 H06 122.3 . . ? C01 C06 H06 122.3 . . ? C011 C010 C09 119.2(3) . . ? C011 C010 N7 119.7(3) . . ? C09 C010 N7 121.1(3) . . ? N6 C09 C08 112.5(3) . . ? N6 C09 C010 131.0(3) . . ? C08 C09 C010 116.5(3) . . ? N2 C02 C01 112.4(3) . . ? N2 C02 C03 131.0(3) . . ? C01 C02 C03 116.6(3) . . ? N2 O1 N1 109.1(2) . . ? C09 N6 O6 105.0(3) . . ? N1 C01 C06 127.5(3) . . ? N1 C01 C02 107.2(3) . . ? C06 C01 C02 125.3(3) . . ? N5 C08 C013 127.7(4) . . ? N5 C08 C09 107.2(3) . . ? C013 C08 C09 125.1(3) . . ? C13 C14 S14 123.7(3) . . ? C13 C14 S13 121.6(3) . . ? S14 C14 S13 114.8(2) . . ? C012 C013 C08 116.0(3) . . ? C012 C013 H013 122.0 . . ? C08 C013 H013 122.0 . . ? C010 C011 C012 121.7(3) . . ? C010 C011 H011 119.1 . . ? C012 C011 H011 119.1 . . ? C06 C05 C04 121.8(3) . . ? C06 C05 C07 120.5(3) . . ? C04 C05 C07 117.6(3) . . ? O3 N3 O4 124.9(3) . . ? O3 N3 C03 117.3(3) . . ? O4 N3 C03 117.8(3) . . ? C03 C04 C05 121.4(3) . . ? C03 C04 H04 119.3 . . ? C05 C04 H04 119.3 . . ? C3 C4 S3 121.5(3) . . ? C3 C4 S4 123.6(3) . . ? S3 C4 S4 114.9(2) . . ? C14 C13 S11 121.2(3) . . ? C14 C13 S12 124.2(3) . . ? S11 C13 S12 114.5(2) . . ? C013 C012 C011 121.4(3) . . ? C013 C012 C014 120.1(3) . . ? C011 C012 C014 118.5(3) . . ? C4 C3 S1 121.8(3) . . ? C4 C3 S2 123.4(3) . . ? S1 C3 S2 114.8(2) . . ? C12 C11 S11 117.3(4) . . ? C12 C11 H11 121.4 . . ? S11 C11 H11 121.4 . . ? C16 C15 S13 117.8(4) . . ? C16 C15 H15 121.1 . . ? S13 C15 H15 121.1 . . ? C2 C1 S1 117.8(3) . . ? C2 C1 H1 121.1 . . ? S1 C1 H1 121.1 . . ? C11 C12 S12 119.0(4) . . ? C11 C12 H12 120.5 . . ? S12 C12 H12 120.5 . . ? N8 C014 C012 178.4(6) . . ? N4 C07 C05 177.3(6) . . ? C1 C2 S2 118.6(3) . . ? C1 C2 H2 120.7 . . ? S2 C2 H2 120.7 . . ? C15 C16 S14 118.9(4) . . ? C15 C16 H16 120.5 . . ? S14 C16 H16 120.5 . . ? C5 C6 S4 119.0(4) . . ? C5 C6 H6 120.5 . . ? S4 C6 H6 120.5 . . ? C6 C5 S3 117.4(4) . . ? C6 C5 H5 121.3 . . ? S3 C5 H5 121.3 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.527 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.084 data_sad2 _database_code_depnum_ccdc_archive 'CCDC 741715' #TrackingRef '- Cif Files.txt' #TrackingRef '- Cif Files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetrathiafulvalene, nitrobenzodithiadiazole ; _chemical_name_common 'tetrathiafulvalene, nitrobenzodithiadiazole' _chemical_melting_point ? _chemical_formula_moiety C24H10N10O4S12 _chemical_formula_sum 'C24 H10 N10 O4 S12' _chemical_formula_weight 887.14 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' 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5426(7) _cell_length_b 9.0675(8) _cell_length_c 13.3535(12) _cell_angle_alpha 75.171(2) _cell_angle_beta 76.615(2) _cell_angle_gamma 73.739(2) _cell_volume 834.88(13) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21434 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 29.63 _exptl_crystal_description parallelepiped _exptl_crystal_colour black _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7872 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6292 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 29.63 _reflns_number_total 4535 _reflns_number_gt 3176 _reflns_threshold_expression >2sigma(I) _computing_data_collection SAINT _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.3549P] 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 4535 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 S1 S 0.36095(11) 0.17401(9) 0.93401(5) 0.0506(2) Uani 1 1 d . . . S2 S 0.24377(12) 0.40310(9) 0.74750(6) 0.0551(2) Uani 1 1 d . . . S3 S 0.41933(12) -0.11127(9) 0.81770(6) 0.0561(2) Uani 1 1 d . . . S4 S 0.30869(11) 0.11285(10) 0.62683(5) 0.0520(2) Uani 1 1 d . . . C1 C 0.2680(5) 0.3672(4) 0.9460(3) 0.0582(8) Uani 1 1 d . . . H1 H 0.2550 0.3972 1.0094 0.070 Uiso 1 1 calc R . . C2 C 0.2161(5) 0.4706(4) 0.8626(3) 0.0611(8) Uani 1 1 d . . . H2 H 0.1663 0.5760 0.8650 0.073 Uiso 1 1 calc R . . C3 C 0.3216(4) 0.2048(3) 0.80499(19) 0.0377(5) Uani 1 1 d . . . C4 C 0.3463(4) 0.0857(3) 0.75593(19) 0.0383(5) Uani 1 1 d . . . C5 C 0.4039(5) -0.1859(4) 0.7133(3) 0.0612(9) Uani 1 1 d . . . H5 H 0.4304 -0.2936 0.7174 0.073 Uiso 1 1 calc R . . C6 C 0.3539(5) -0.0867(4) 0.6284(3) 0.0607(9) Uani 1 1 d . . . H6 H 0.3430 -0.1218 0.5709 0.073 Uiso 1 1 calc R . . C7 C -0.1750(4) 0.2334(4) 0.8042(2) 0.0480(7) Uani 1 1 d . . . C8 C -0.1268(4) 0.0759(4) 0.8338(2) 0.0526(7) Uani 1 1 d . . . H8 H -0.0968 0.0291 0.9002 0.063 Uiso 1 1 calc R . . C9 C -0.1222(4) -0.0185(3) 0.7620(2) 0.0456(6) Uani 1 1 d . . . C10 C -0.1666(4) 0.0483(3) 0.6598(2) 0.0403(6) Uani 1 1 d . . . C11 C -0.2104(4) 0.2164(3) 0.6278(2) 0.0395(5) Uani 1 1 d . . . C12 C -0.2147(4) 0.3097(3) 0.7001(2) 0.0409(6) Uani 1 1 d . . . N1 N -0.1948(4) 0.3286(4) 0.8823(2) 0.0672(8) Uani 1 1 d . . . O1 O -0.2777(5) 0.4660(4) 0.8631(3) 0.1094(12) Uani 1 1 d . . . O2 O -0.1292(4) 0.2636(4) 0.96224(19) 0.0912(10) Uani 1 1 d . . . N2 N -0.0822(4) -0.1753(3) 0.7829(2) 0.0611(7) Uani 1 1 d . . . N3 N -0.1604(4) -0.0565(3) 0.6038(2) 0.0525(6) Uani 1 1 d . . . N4 N -0.2453(4) 0.2989(3) 0.5337(2) 0.0557(6) Uani 1 1 d . . . N5 N -0.2518(4) 0.4634(3) 0.6576(2) 0.0598(7) Uani 1 1 d . . . S5 S -0.10175(13) -0.22651(9) 0.68007(8) 0.0652(3) Uani 1 1 d . . . S6 S -0.27794(15) 0.48092(10) 0.53877(8) 0.0714(3) 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 S1 0.0652(5) 0.0461(4) 0.0383(3) -0.0119(3) -0.0177(3) 0.0003(3) S2 0.0743(5) 0.0386(4) 0.0470(4) -0.0036(3) -0.0179(4) -0.0033(3) S3 0.0742(5) 0.0385(4) 0.0521(4) -0.0104(3) -0.0112(4) -0.0063(3) S4 0.0597(5) 0.0616(5) 0.0376(3) -0.0160(3) -0.0104(3) -0.0121(4) C1 0.076(2) 0.0510(17) 0.0519(17) -0.0244(14) -0.0103(15) -0.0107(15) C2 0.078(2) 0.0376(15) 0.067(2) -0.0200(14) -0.0116(17) -0.0058(15) C3 0.0402(14) 0.0374(13) 0.0333(12) -0.0069(10) -0.0074(10) -0.0055(10) C4 0.0375(14) 0.0406(13) 0.0352(12) -0.0096(10) -0.0038(10) -0.0070(10) C5 0.069(2) 0.0475(17) 0.073(2) -0.0313(16) 0.0039(17) -0.0189(15) C6 0.061(2) 0.076(2) 0.0604(19) -0.0389(18) 0.0007(15) -0.0264(17) C7 0.0464(16) 0.0612(18) 0.0477(15) -0.0272(13) -0.0011(12) -0.0215(13) C8 0.0523(18) 0.072(2) 0.0393(14) -0.0086(13) -0.0093(12) -0.0249(15) C9 0.0413(15) 0.0423(14) 0.0530(16) -0.0066(12) -0.0073(12) -0.0131(12) C10 0.0403(14) 0.0363(13) 0.0481(14) -0.0142(11) -0.0075(11) -0.0099(10) C11 0.0420(14) 0.0372(13) 0.0438(13) -0.0145(11) -0.0091(11) -0.0095(10) C12 0.0377(14) 0.0405(13) 0.0512(15) -0.0201(11) -0.0068(11) -0.0109(11) N1 0.0710(19) 0.095(2) 0.0554(17) -0.0401(16) 0.0019(14) -0.0383(18) O1 0.139(3) 0.100(2) 0.107(2) -0.074(2) -0.031(2) -0.001(2) O2 0.122(2) 0.130(3) 0.0471(14) -0.0303(15) -0.0122(15) -0.062(2) N2 0.0642(17) 0.0424(14) 0.0738(18) -0.0025(12) -0.0174(14) -0.0117(12) N3 0.0592(15) 0.0398(12) 0.0642(16) -0.0220(11) -0.0102(12) -0.0109(11) N4 0.0761(18) 0.0434(13) 0.0535(14) -0.0095(11) -0.0263(13) -0.0116(12) N5 0.0666(17) 0.0413(13) 0.0790(18) -0.0245(13) -0.0145(14) -0.0118(12) S5 0.0714(6) 0.0356(4) 0.0892(6) -0.0194(4) -0.0113(5) -0.0096(4) S6 0.0995(7) 0.0390(4) 0.0776(6) -0.0036(4) -0.0354(5) -0.0108(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 S1 C1 1.729(3) . ? S1 C3 1.755(2) . ? S2 C2 1.744(3) . ? S2 C3 1.755(3) . ? S3 C5 1.737(3) . ? S3 C4 1.755(3) . ? S4 C6 1.740(4) . ? S4 C4 1.756(3) . ? C1 C2 1.318(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.350(4) . ? C5 C6 1.313(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.347(4) . ? C7 C12 1.444(4) . ? C7 N1 1.473(4) . ? C8 C9 1.428(4) . ? C8 H8 0.9300 . ? C9 N2 1.337(4) . ? C9 C10 1.420(4) . ? C10 N3 1.337(3) . ? C10 C11 1.437(4) . ? C11 N4 1.330(3) . ? C11 C12 1.427(3) . ? C12 N5 1.339(4) . ? N1 O1 1.218(4) . ? N1 O2 1.221(4) . ? N2 S5 1.607(3) . ? N3 S5 1.622(3) . ? N4 S6 1.616(3) . ? N5 S6 1.607(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 C1 S1 C3 95.15(14) . . ? C2 S2 C3 94.74(14) . . ? C5 S3 C4 94.57(15) . . ? C6 S4 C4 94.73(15) . . ? C2 C1 S1 117.9(2) . . ? C2 C1 H1 121.0 . . ? S1 C1 H1 121.0 . . ? C1 C2 S2 117.8(2) . . ? C1 C2 H2 121.1 . . ? S2 C2 H2 121.1 . . ? C4 C3 S2 123.6(2) . . ? C4 C3 S1 122.6(2) . . ? S2 C3 S1 113.80(14) . . ? C3 C4 S3 122.0(2) . . ? C3 C4 S4 123.6(2) . . ? S3 C4 S4 114.38(15) . . ? C6 C5 S3 118.4(2) . . ? C6 C5 H5 120.8 . . ? S3 C5 H5 120.8 . . ? C5 C6 S4 117.8(2) . . ? C5 C6 H6 121.1 . . ? S4 C6 H6 121.1 . . ? C8 C7 C12 121.7(2) . . ? C8 C7 N1 118.5(3) . . ? C12 C7 N1 119.8(3) . . ? C7 C8 C9 119.3(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? N2 C9 C10 112.8(3) . . ? N2 C9 C8 125.1(3) . . ? C10 C9 C8 122.1(3) . . ? N3 C10 C9 114.5(2) . . ? N3 C10 C11 127.6(3) . . ? C9 C10 C11 118.0(2) . . ? N4 C11 C12 114.2(2) . . ? N4 C11 C10 126.4(2) . . ? C12 C11 C10 119.5(2) . . ? N5 C12 C11 112.3(2) . . ? N5 C12 C7 128.3(2) . . ? C11 C12 C7 119.4(2) . . ? O1 N1 O2 124.7(3) . . ? O1 N1 C7 117.6(3) . . ? O2 N1 C7 117.7(3) . . ? C9 N2 S5 106.6(2) . . ? C10 N3 S5 105.2(2) . . ? C11 N4 S6 105.96(19) . . ? C12 N5 S6 106.9(2) . . ? N2 S5 N3 101.00(13) . . ? N5 S6 N4 100.62(13) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 29.63 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.595 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.069 data_sad1 _database_code_depnum_ccdc_archive 'CCDC 741716' #TrackingRef '- Cif Files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,cyano-4,nitrobenzofuroxane ; _chemical_name_common 6,cyano-4,nitrobenzofuroxane _chemical_melting_point ? _chemical_formula_moiety C28H8N16O16 _chemical_formula_sum 'C28 H8 N16 O16' _chemical_formula_weight 824.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 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 9.8632(19) _cell_length_b 8.1924(16) _cell_length_c 10.800(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.484(4) _cell_angle_gamma 90.00 _cell_volume 812.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6119 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 29.57 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9320 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5836 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 29.57 _reflns_number_total 2272 _reflns_number_gt 1510 _reflns_threshold_expression >2sigma(I) _computing_data_collection SAINT _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.0472P] 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 SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2272 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 C1 C 0.18770(13) -0.03755(17) 0.29230(12) 0.0346(3) Uani 1 1 d . . . N1 N 0.11882(12) -0.08430(15) 0.37189(11) 0.0408(3) Uani 1 1 d . . . N2 N 0.12880(14) 0.19563(16) 0.37362(12) 0.0481(3) Uani 1 1 d . . . O1 O 0.08614(11) -0.21475(14) 0.40721(11) 0.0542(3) Uani 1 1 d . . . O2 O 0.08035(12) 0.06235(14) 0.42252(10) 0.0518(3) Uani 1 1 d . . . C2 C 0.19317(13) 0.13413(17) 0.29630(12) 0.0351(3) Uani 1 1 d . . . C3 C 0.26630(13) 0.21070(15) 0.22020(12) 0.0355(3) Uani 1 1 d . . . N3 N 0.27890(13) 0.38802(15) 0.22077(12) 0.0456(3) Uani 1 1 d . . . O3 O 0.21548(15) 0.46418(15) 0.27987(14) 0.0689(4) Uani 1 1 d . . . O4 O 0.35190(14) 0.44961(14) 0.16399(14) 0.0651(4) Uani 1 1 d . . . C4 C 0.32514(13) 0.12018(17) 0.14907(12) 0.0368(3) Uani 1 1 d . . . H4 H 0.3733 0.1716 0.1002 0.044 Uiso 1 1 calc R . . C5 C 0.31495(13) -0.05401(17) 0.14737(12) 0.0355(3) Uani 1 1 d . . . C6 C 0.24702(13) -0.13475(18) 0.21827(12) 0.0368(3) Uani 1 1 d . . . H6 H 0.2404 -0.2480 0.2176 0.044 Uiso 1 1 calc R . . C7 C 0.38400(14) -0.14234(18) 0.07188(13) 0.0408(3) Uani 1 1 d . . . N4 N 0.44348(15) -0.21010(18) 0.01558(14) 0.0556(4) 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 C1 0.0351(6) 0.0389(7) 0.0325(6) 0.0016(5) 0.0155(5) -0.0016(5) N1 0.0415(6) 0.0473(7) 0.0389(6) 0.0021(5) 0.0210(5) -0.0025(5) N2 0.0560(7) 0.0488(7) 0.0462(6) -0.0064(6) 0.0267(6) 0.0009(6) O1 0.0585(6) 0.0551(7) 0.0585(6) 0.0115(5) 0.0327(5) -0.0072(5) O2 0.0588(7) 0.0605(7) 0.0485(6) -0.0045(5) 0.0343(5) 0.0011(5) C2 0.0361(6) 0.0360(7) 0.0329(6) -0.0028(5) 0.0124(5) 0.0012(5) C3 0.0380(6) 0.0302(7) 0.0364(6) 0.0015(5) 0.0115(5) -0.0009(5) N3 0.0481(7) 0.0328(6) 0.0509(7) 0.0017(5) 0.0122(5) -0.0024(5) O3 0.0802(9) 0.0377(6) 0.0942(10) -0.0146(6) 0.0385(8) 0.0016(6) O4 0.0710(8) 0.0441(7) 0.0816(8) 0.0139(6) 0.0294(7) -0.0114(5) C4 0.0378(6) 0.0391(8) 0.0352(6) 0.0051(5) 0.0153(5) -0.0019(5) C5 0.0365(6) 0.0382(7) 0.0346(6) -0.0017(5) 0.0163(5) 0.0008(5) C6 0.0428(7) 0.0317(7) 0.0389(6) -0.0011(5) 0.0186(5) 0.0000(5) C7 0.0438(7) 0.0425(8) 0.0404(7) -0.0001(6) 0.0205(6) -0.0007(6) N4 0.0600(8) 0.0608(9) 0.0574(7) -0.0070(6) 0.0349(6) 0.0021(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 C1 N1 1.3322(17) . ? C1 C6 1.3994(18) . ? C1 C2 1.408(2) . ? N1 O1 1.2172(15) . ? N1 O2 1.4278(16) . ? N2 C2 1.3200(17) . ? N2 O2 1.3727(17) . ? C2 C3 1.4225(18) . ? C3 C4 1.3429(17) . ? C3 N3 1.4578(19) . ? N3 O4 1.2135(17) . ? N3 O3 1.2168(18) . ? C4 C5 1.430(2) . ? C4 H4 0.9300 . ? C5 C6 1.3596(17) . ? C5 C7 1.4350(18) . ? C6 H6 0.9300 . ? C7 N4 1.1328(18) . ? 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 N1 C1 C6 128.59(13) . . ? N1 C1 C2 106.88(12) . . ? C6 C1 C2 124.52(12) . . ? O1 N1 C1 135.30(13) . . ? O1 N1 O2 118.73(11) . . ? C1 N1 O2 105.97(11) . . ? C2 N2 O2 104.82(11) . . ? N2 O2 N1 110.06(10) . . ? N2 C2 C1 112.26(12) . . ? N2 C2 C3 131.32(13) . . ? C1 C2 C3 116.41(11) . . ? C4 C3 C2 120.26(12) . . ? C4 C3 N3 119.91(12) . . ? C2 C3 N3 119.83(12) . . ? O4 N3 O3 124.47(14) . . ? O4 N3 C3 118.53(13) . . ? O3 N3 C3 116.99(13) . . ? C3 C4 C5 121.01(11) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 121.67(12) . . ? C6 C5 C7 120.59(12) . . ? C4 C5 C7 117.69(11) . . ? C5 C6 C1 116.12(13) . . ? C5 C6 H6 121.9 . . ? C1 C6 H6 121.9 . . ? N4 C7 C5 177.40(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.327 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.056