Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_contact_author 'Prof M Bryce' _publ_contact_author_address ; Prof M Bryce Department of Chemistry University of Durham South Road DURHAM DH1 3LE UK ; _publ_contact_author_email 'M.R.BRYCE@DURHAM.AC.UK' loop_ _publ_author_name 'Perepicjka, Igor F.' 'Perepicjka, Dmitrii F.' 'Lyubchik, Svetlana B.' 'Bryce, Martin R.' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' _journal_name_full 'Journal of the Chemical Society. Perkin Transactions 2' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2001' _publ_section_title ; Electron Acceptors of the Fluorene Series. 13. 1 9-(5-Nitrofuran-2-ylidene)- and 9-(5-nitrothien-2-ylidene)-2,4,5,7-tetranitrofluorenes: novel n-extended electron acceptors. Synthesis, cyclic voltammetry, X-ray crystal structures for the acceptor and its 4,5-dimethyltetrathiafulvalene complex, and a theoretical study. ; #====================================================================== data_2a _database_code_CSD 164242 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(5-nitrofuran-2-ylidene)-2,4,5,7-tetranitrofluorene: dioxane (1:2) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H7 N5 O11,(C4 H8 O2)2' _chemical_formula_sum 'C26 H23 N5 O15' _chemical_formula_weight 645.49 _ccdc_disorder ; Atoms O(31) and O(34) in one of the dioxane molecules are disordered over two positions, with occupancies 59% (unprimed) and 41% (primed). Consequently, all methylene H atoms of this molecule are also disordered. ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 '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 15.588(5) _cell_length_b 8.667(3) _cell_length_c 21.798(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.43(2) _cell_angle_gamma 90.00 _cell_volume 2777.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.6 _cell_measurement_theta_max 23.3 _exptl_crystal_description plate _exptl_crystal_colour amber _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 1.120 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8493 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'T_max,min from psi-scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3426 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 49.99 _reflns_number_total 2770 _reflns_number_gt 2236 _reflns_threshold_expression >2sigma(I) _computing_data_collection AFC/MSC _computing_cell_refinement AFC/MSC _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.0478P)^2^+1.2514P] 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 0.00099(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2770 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 O1 O 0.59179(15) 0.3916(3) 0.50299(10) 0.0394(6) Uani 1 1 d . . . O2 O 0.73832(16) 0.4063(2) 0.53394(9) 0.0363(6) Uani 1 1 d . . . O3 O 0.90349(14) 0.4467(3) 0.76953(10) 0.0404(6) Uani 1 1 d . . . O4 O 0.85174(13) 0.6525(3) 0.80236(10) 0.0346(6) Uani 1 1 d . . . O5 O 0.80064(14) 0.3741(3) 0.85807(10) 0.0394(6) Uani 1 1 d . . . O6 O 0.84648(14) 0.5587(3) 0.92939(10) 0.0472(7) Uani 1 1 d . . . O7 O 0.57925(15) 0.6946(3) 0.99089(10) 0.0505(7) Uani 1 1 d . . . O8 O 0.44664(17) 0.7017(3) 0.91700(10) 0.0505(7) Uani 1 1 d . . . O9 O 0.30082(16) 0.8836(3) 0.81301(11) 0.0497(7) Uani 1 1 d . . . O10 O 0.16623(18) 0.9421(3) 0.74617(12) 0.0556(7) Uani 1 1 d . . . O11 O 0.34853(13) 0.7646(2) 0.71979(8) 0.0258(5) Uani 1 1 d . . . N2 N 0.6660(2) 0.4186(3) 0.54399(11) 0.0288(7) Uani 1 1 d . . . N4 N 0.84228(18) 0.5363(3) 0.76777(11) 0.0296(7) Uani 1 1 d . . . N5 N 0.78888(18) 0.4953(3) 0.88354(12) 0.0329(7) Uani 1 1 d . . . N7 N 0.5291(2) 0.6845(3) 0.93418(13) 0.0344(7) Uani 1 1 d . . . N18 N 0.2426(2) 0.8855(3) 0.75899(14) 0.0367(7) Uani 1 1 d . . . C1 C 0.5879(2) 0.5068(3) 0.61781(13) 0.0251(8) Uani 1 1 d . . . H1 H 0.5323 0.5065 0.5823 0.030 Uiso 1 1 d R . . C2 C 0.6678(2) 0.4660(3) 0.60920(13) 0.0245(8) Uani 1 1 d . . . C3 C 0.7513(2) 0.4714(3) 0.65826(14) 0.0257(7) Uani 1 1 d . . . H3 H 0.8060 0.4487 0.6499 0.031 Uiso 1 1 d R . . C4 C 0.75204(19) 0.5116(3) 0.71968(13) 0.0229(8) Uani 1 1 d . . . C5 C 0.69838(19) 0.5660(3) 0.85870(13) 0.0232(7) Uani 1 1 d . . . C6 C 0.6606(2) 0.6066(3) 0.90516(14) 0.0261(8) Uani 1 1 d . . . H6 H 0.6957 0.6056 0.9501 0.031 Uiso 1 1 d R . . C7 C 0.5704(2) 0.6495(3) 0.88446(13) 0.0233(7) Uani 1 1 d . . . C8 C 0.5169(2) 0.6538(3) 0.82014(13) 0.0239(7) Uani 1 1 d . . . H8 H 0.4544 0.6812 0.8080 0.029 Uiso 1 1 d R . . C9 C 0.51608(19) 0.6036(3) 0.70195(13) 0.0212(7) Uani 1 1 d . . . C10 C 0.59016(19) 0.5481(3) 0.67995(13) 0.0220(7) Uani 1 1 d . . . C11 C 0.6721(2) 0.5426(3) 0.73313(13) 0.0221(7) Uani 1 1 d . . . C12 C 0.6499(2) 0.5757(3) 0.79232(13) 0.0221(7) Uani 1 1 d . . . C13 C 0.55610(19) 0.6176(3) 0.77334(13) 0.0216(7) Uani 1 1 d . . . C14 C 0.43261(19) 0.6348(3) 0.65833(13) 0.0247(8) Uani 1 1 d . . . H14 H 0.4271 0.6040 0.6154 0.030 Uiso 1 1 d R . . C15 C 0.3516(2) 0.7016(3) 0.66246(13) 0.0235(8) Uani 1 1 d . . . C16 C 0.2681(2) 0.7171(3) 0.61564(14) 0.0269(8) Uani 1 1 d . . . H16 H 0.2521 0.6836 0.5718 0.032 Uiso 1 1 d R . . C17 C 0.2105(2) 0.7908(3) 0.64385(14) 0.0280(8) Uani 1 1 d . . . H17 H 0.1483 0.8173 0.6236 0.034 Uiso 1 1 d R . . C18 C 0.2626(2) 0.8161(3) 0.70609(14) 0.0252(8) Uani 1 1 d . . . O21 O 0.55282(16) 0.9940(3) 0.87855(13) 0.0515(7) Uani 1 1 d . . . C22 C 0.4895(2) 1.0673(4) 0.8235(2) 0.0530(10) Uani 1 1 d . . . H221 H 0.4284 1.0667 0.8280 0.069 Uiso 1 1 d R . . H222 H 0.4859 1.0092 0.7836 0.069 Uiso 1 1 d R . . C23 C 0.5176(3) 1.2289(4) 0.81730(17) 0.0494(10) Uani 1 1 d . . . H231 H 0.5772 1.2295 0.8103 0.064 Uiso 1 1 d R . . H232 H 0.4723 1.2782 0.7792 0.064 Uiso 1 1 d R . . O24 O 0.52328(15) 1.3141(3) 0.87465(11) 0.0474(6) Uani 1 1 d . . . C25 C 0.5861(2) 1.2412(4) 0.92980(17) 0.0473(10) Uani 1 1 d . . . H251 H 0.5884 1.2986 0.9696 0.062 Uiso 1 1 d R . . H252 H 0.6476 1.2432 0.9260 0.062 Uiso 1 1 d R . . C26 C 0.5589(3) 1.0803(4) 0.93585(18) 0.0514(10) Uani 1 1 d . . . H261 H 0.6043 1.0311 0.9739 0.067 Uiso 1 1 d R . . H262 H 0.4994 1.0791 0.9431 0.067 Uiso 1 1 d R . . O31 O 0.6545(3) 0.7347(5) 0.4658(2) 0.0607(13) Uani 0.59 1 d P A 1 O31' O 0.5923(4) 0.7035(8) 0.4111(3) 0.0616(18) Uiso 0.41 1 d P A 2 C32 C 0.5678(3) 0.8205(4) 0.4390(2) 0.0618(11) Uani 1 1 d . . . H321 H 0.5422 0.8386 0.4728 0.074 Uiso 0.59 1 d PR A 1 H322 H 0.5248 0.7626 0.4049 0.074 Uiso 0.59 1 d PR A 1 H323 H 0.5035 0.8140 0.4310 0.074 Uiso 0.41 1 d PR A 2 H324 H 0.5980 0.8174 0.4852 0.074 Uiso 0.41 1 d PR A 2 C33 C 0.5902(2) 0.9714(4) 0.4145(2) 0.0603(12) Uani 1 1 d . A . H331 H 0.6293 1.0319 0.4496 0.072 Uiso 0.59 1 d PR B 1 H332 H 0.5349 1.0281 0.3951 0.072 Uiso 0.59 1 d PR B 1 H333 H 0.5586 1.0554 0.4262 0.072 Uiso 0.41 1 d PR B 2 H334 H 0.5747 0.9682 0.3681 0.072 Uiso 0.41 1 d PR B 2 O34 O 0.6369(3) 0.9429(4) 0.36224(16) 0.0408(10) Uani 0.59 1 d P A 1 O34' O 0.6876(4) 0.9841(7) 0.4456(3) 0.0527(16) Uiso 0.41 1 d P A 2 C35 C 0.7185(3) 0.8652(4) 0.3999(2) 0.0620(11) Uani 1 1 d . . . H351 H 0.7522 0.9278 0.4363 0.074 Uiso 0.59 1 d PR A 1 H352 H 0.7557 0.8490 0.3731 0.074 Uiso 0.59 1 d PR A 1 H353 H 0.6838 0.8810 0.3549 0.074 Uiso 0.41 1 d PR A 2 H354 H 0.7821 0.8741 0.4057 0.074 Uiso 0.41 1 d PR A 2 C36 C 0.6960(3) 0.7124(4) 0.4233(2) 0.0593(11) Uani 1 1 d . A . H361 H 0.6575 0.6534 0.3874 0.071 Uiso 0.59 1 d PR C 1 H362 H 0.7511 0.6554 0.4428 0.071 Uiso 0.59 1 d PR C 1 H363 H 0.7302 0.7012 0.4687 0.071 Uiso 0.41 1 d PR C 2 H364 H 0.7129 0.6302 0.4001 0.071 Uiso 0.41 1 d PR C 2 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 O1 0.0324(14) 0.0600(16) 0.0216(12) -0.0040(11) 0.0034(11) 0.0093(12) O2 0.0323(15) 0.0513(15) 0.0301(12) -0.0027(11) 0.0167(11) 0.0069(11) O3 0.0238(13) 0.0552(16) 0.0390(14) -0.0085(11) 0.0061(10) 0.0145(13) O4 0.0285(13) 0.0400(14) 0.0316(12) -0.0092(12) 0.0051(10) -0.0041(11) O5 0.0435(15) 0.0403(15) 0.0346(13) 0.0041(12) 0.0130(11) 0.0134(12) O6 0.0290(14) 0.0744(18) 0.0290(13) -0.0104(13) -0.0026(11) 0.0048(13) O7 0.0425(14) 0.088(2) 0.0192(13) -0.0057(12) 0.0080(12) 0.0053(14) O8 0.0307(16) 0.093(2) 0.0306(13) -0.0037(13) 0.0144(11) 0.0049(14) O9 0.0405(15) 0.0758(19) 0.0323(14) -0.0196(13) 0.0116(13) -0.0026(13) O10 0.0384(16) 0.0660(18) 0.0621(16) -0.0205(14) 0.0161(12) 0.0178(14) O11 0.0241(14) 0.0296(12) 0.0243(12) -0.0042(10) 0.0089(9) 0.0022(10) N2 0.0286(19) 0.0359(17) 0.0227(15) 0.0012(12) 0.0096(15) 0.0082(14) N4 0.0248(18) 0.0368(18) 0.0262(15) -0.0066(14) 0.0071(13) -0.0040(15) N5 0.0331(19) 0.0413(19) 0.0225(16) 0.0005(14) 0.0068(14) 0.0039(15) N7 0.035(2) 0.0467(18) 0.0227(17) -0.0021(13) 0.0108(15) -0.0019(14) N18 0.0333(19) 0.0397(17) 0.0405(19) -0.0117(15) 0.0169(16) -0.0029(15) C1 0.025(2) 0.0305(19) 0.0182(18) 0.0033(14) 0.0050(14) 0.0009(15) C2 0.028(2) 0.0285(18) 0.0189(17) -0.0002(14) 0.0102(16) 0.0042(15) C3 0.0231(19) 0.0260(18) 0.0288(19) -0.0021(15) 0.0097(15) 0.0022(15) C4 0.021(2) 0.0235(17) 0.0205(17) -0.0019(14) 0.0016(14) -0.0004(14) C5 0.0158(17) 0.0279(18) 0.0221(18) -0.0004(14) 0.0011(14) 0.0020(15) C6 0.032(2) 0.0262(18) 0.0193(16) -0.0021(14) 0.0073(15) -0.0012(15) C7 0.025(2) 0.0302(18) 0.0152(17) -0.0013(14) 0.0074(15) -0.0004(15) C8 0.0200(18) 0.0250(17) 0.0265(19) -0.0011(14) 0.0074(15) -0.0013(14) C9 0.0212(19) 0.0242(17) 0.0183(17) -0.0008(13) 0.0067(15) -0.0011(14) C10 0.0230(18) 0.0228(17) 0.0208(17) -0.0001(13) 0.0080(15) -0.0017(14) C11 0.0229(19) 0.0193(17) 0.0239(17) -0.0022(13) 0.0072(15) -0.0019(14) C12 0.026(2) 0.0188(17) 0.0210(18) -0.0027(13) 0.0077(14) -0.0010(14) C13 0.021(2) 0.0221(17) 0.0221(17) -0.0014(14) 0.0071(14) 0.0012(14) C14 0.026(2) 0.0306(19) 0.0203(17) -0.0036(14) 0.0107(15) -0.0019(16) C15 0.027(2) 0.0278(18) 0.0168(17) -0.0002(14) 0.0085(16) -0.0010(15) C16 0.027(2) 0.0316(19) 0.0223(17) 0.0012(15) 0.0079(17) -0.0002(16) C17 0.0218(18) 0.0290(19) 0.031(2) 0.0023(15) 0.0064(16) 0.0005(15) C18 0.022(2) 0.0257(18) 0.031(2) -0.0019(15) 0.0127(15) 0.0027(15) O21 0.0530(17) 0.0304(14) 0.0803(19) -0.0007(14) 0.0344(15) 0.0036(12) C22 0.039(2) 0.043(2) 0.080(3) -0.021(2) 0.024(2) -0.008(2) C23 0.053(3) 0.041(2) 0.052(2) -0.0003(19) 0.0145(19) 0.0010(19) O24 0.0532(16) 0.0313(14) 0.0553(15) -0.0007(13) 0.0148(13) 0.0031(12) C25 0.049(2) 0.042(2) 0.052(2) -0.0019(19) 0.019(2) 0.0004(19) C26 0.059(3) 0.042(2) 0.066(3) 0.007(2) 0.037(2) 0.006(2) O31 0.075(3) 0.059(3) 0.065(3) 0.039(2) 0.045(3) 0.023(3) C32 0.052(3) 0.048(3) 0.079(3) 0.003(2) 0.013(2) -0.007(2) C33 0.035(2) 0.043(2) 0.093(3) 0.014(2) 0.009(2) 0.0033(19) O34 0.047(2) 0.037(2) 0.034(2) 0.0044(18) 0.0077(19) -0.001(2) C35 0.054(3) 0.040(2) 0.095(3) 0.002(2) 0.028(2) 0.003(2) C36 0.056(3) 0.039(2) 0.075(3) 0.012(2) 0.011(2) 0.003(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 O1 N2 1.226(3) . ? O2 N2 1.223(3) . ? O3 N4 1.221(3) . ? O4 N4 1.237(3) . ? O5 N5 1.229(3) . ? O6 N5 1.229(3) . ? O7 N7 1.227(3) . ? O8 N7 1.222(3) . ? O9 N18 1.225(3) . ? O10 N18 1.230(3) . ? O11 C18 1.347(3) . ? O11 C15 1.379(3) . ? N2 C2 1.471(4) . ? N4 C4 1.464(4) . ? N5 C5 1.467(4) . ? N7 C7 1.465(4) . ? N18 C18 1.424(4) . ? C1 C2 1.367(4) . ? C1 C10 1.390(4) . ? C2 C3 1.384(4) . ? C3 C4 1.380(4) . ? C4 C11 1.398(4) . ? C5 C6 1.376(4) . ? C5 C12 1.394(4) . ? C6 C7 1.377(4) . ? C7 C8 1.373(4) . ? C8 C13 1.389(4) . ? C9 C14 1.359(4) . ? C9 C10 1.471(4) . ? C9 C13 1.476(4) . ? C10 C11 1.411(4) . ? C11 C12 1.471(4) . ? C12 C13 1.428(4) . ? C14 C15 1.419(4) . ? C15 C16 1.368(4) . ? C16 C17 1.400(4) . ? C17 C18 1.347(4) . ? O21 C22 1.425(4) . ? O21 C26 1.432(4) . ? C22 C23 1.487(5) . ? C23 O24 1.429(4) . ? O24 C25 1.421(4) . ? C25 C26 1.476(5) . ? O31 C36 1.309(5) . ? O31 C32 1.482(5) . ? O31' C32 1.304(7) . ? O31' C36 1.550(8) . ? C32 C33 1.497(5) . ? C33 O34' 1.446(7) . ? C33 O34 1.563(5) . ? O34 C35 1.432(5) . ? O34' C35 1.616(7) . ? C35 C36 1.502(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 C18 O11 C15 105.2(2) . . ? O2 N2 O1 123.7(2) . . ? O2 N2 C2 118.3(3) . . ? O1 N2 C2 117.9(3) . . ? O3 N4 O4 124.4(2) . . ? O3 N4 C4 119.0(2) . . ? O4 N4 C4 116.5(3) . . ? O6 N5 O5 124.8(3) . . ? O6 N5 C5 117.8(3) . . ? O5 N5 C5 117.4(3) . . ? O8 N7 O7 123.6(3) . . ? O8 N7 C7 118.4(3) . . ? O7 N7 C7 118.1(3) . . ? O9 N18 O10 125.1(3) . . ? O9 N18 C18 118.7(3) . . ? O10 N18 C18 116.2(3) . . ? C2 C1 C10 118.1(3) . . ? C1 C2 C3 123.4(3) . . ? C1 C2 N2 118.7(3) . . ? C3 C2 N2 117.9(3) . . ? C4 C3 C2 117.4(3) . . ? C3 C4 C11 122.1(3) . . ? C3 C4 N4 115.3(3) . . ? C11 C4 N4 122.2(2) . . ? C6 C5 C12 122.1(3) . . ? C6 C5 N5 115.5(2) . . ? C12 C5 N5 122.1(3) . . ? C5 C6 C7 117.9(3) . . ? C8 C7 C6 123.3(3) . . ? C8 C7 N7 118.8(3) . . ? C6 C7 N7 117.8(3) . . ? C7 C8 C13 118.5(3) . . ? C14 C9 C10 120.6(2) . . ? C14 C9 C13 133.8(3) . . ? C10 C9 C13 105.6(2) . . ? C1 C10 C11 121.0(3) . . ? C1 C10 C9 129.3(3) . . ? C11 C10 C9 109.7(2) . . ? C4 C11 C10 117.4(2) . . ? C4 C11 C12 135.0(3) . . ? C10 C11 C12 107.5(2) . . ? C5 C12 C13 117.7(3) . . ? C5 C12 C11 133.9(3) . . ? C13 C12 C11 108.2(2) . . ? C8 C13 C12 120.2(2) . . ? C8 C13 C9 131.1(3) . . ? C12 C13 C9 108.5(2) . . ? C9 C14 C15 134.6(3) . . ? C16 C15 O11 109.0(2) . . ? C16 C15 C14 129.7(3) . . ? O11 C15 C14 121.2(3) . . ? C15 C16 C17 107.9(2) . . ? C18 C17 C16 104.8(3) . . ? O11 C18 C17 113.1(3) . . ? O11 C18 N18 115.5(3) . . ? C17 C18 N18 131.5(3) . . ? C22 O21 C26 109.2(3) . . ? O21 C22 C23 110.7(3) . . ? O24 C23 C22 110.0(3) . . ? C25 O24 C23 109.6(3) . . ? O24 C25 C26 111.0(3) . . ? O21 C26 C25 110.7(3) . . ? C36 O31 C32 113.3(4) . . ? C32 O31' C36 109.4(5) . . ? O31' C32 O31 54.8(3) . . ? O31' C32 C33 112.0(4) . . ? O31 C32 C33 106.7(3) . . ? O34' C33 C32 103.5(4) . . ? O34' C33 O34 71.5(3) . . ? C32 C33 O34 110.0(3) . . ? C35 O34 C33 101.3(3) . . ? C33 O34' C35 98.3(4) . . ? O34 C35 C36 110.2(3) . . ? O34 C35 O34' 70.3(3) . . ? C36 C35 O34' 101.6(4) . . ? O31 C36 C35 109.6(4) . . ? O31 C36 O31' 52.9(3) . . ? C35 C36 O31' 109.5(4) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 49.99 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.216 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.041 #===========================================END data_2b _database_code_CSD 164243 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(5-nitrofuran-2-ylidene)-2,4,5,7-tetranitrofluorene : 3,4-dimethyltetrathiafulvalene : acetonitrile (2:2:1) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H7 N5 O11,C8 H8 S4,0.5(C2 H3 N)' _chemical_formula_sum 'C27 H16.50 N5.50 O11 S4' _chemical_formula_weight 722.20 _ccdc_disorder ; N(18) and O(10) are disordered between positions A and B with equal probability. The MeCN molecule N(19)C(19)C(20) is disordered between two positions, related via an inversion centre. ; 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 16.872(3) _cell_length_b 7.755(1) _cell_length_c 23.201(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.99(1) _cell_angle_gamma 90.00 _cell_volume 2946(1) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 358 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 20.2 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1476 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 1.00 0.0100 1.00 0.00 -1.00 0.0100 0.00 1.00 0.00 0.1400 0.00 -1.00 0.00 0.1400 0.00 0.00 -1.00 0.0900 0.00 0.00 1.00 0.0900 _exptl_special_details ;The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (30 sec exposure) covering 0.3\% in \w. Crystal to detector distance 6.0 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 10116 _diffrn_reflns_av_R_equivalents 0.0872 _diffrn_reflns_av_sigmaI/netI 0.1116 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 24.92 _reflns_number_total 3668 _reflns_number_gt 2120 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Twinned crystal: imperfect overlap of reflections with h+l=5n, which were omitted from refinement (for n=-5 to -1, 1 to 5, 770 reflections omitted). On all reflections R_gt=0.118. 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. ; _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^)+(0.1089P)^2^+0.7366P] 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 3668 _refine_ls_number_parameters 427 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1504 _refine_ls_R_factor_gt 0.0816 _refine_ls_wR_factor_ref 0.2120 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.005 _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 0.71786(15) 0.1863(3) 0.45064(12) 0.0446(7) Uani 1 1 d . . . S2 S 0.57923(15) 0.3764(3) 0.47634(11) 0.0466(7) Uani 1 1 d . . . S3 S 0.61630(15) 0.1468(3) 0.31084(11) 0.0429(7) Uani 1 1 d . . . S4 S 0.47461(14) 0.3218(3) 0.33975(12) 0.0446(7) Uani 1 1 d . . . O1 O 0.4098(3) 1.0799(8) 0.4711(2) 0.0349(15) Uani 1 1 d . . . O2 O 0.2879(3) 1.0741(7) 0.4118(2) 0.0255(13) Uani 1 1 d . . . O3 O 0.2445(3) 0.8092(8) 0.2177(2) 0.0437(16) Uani 1 1 d . . . O4 O 0.3298(3) 0.6027(7) 0.2140(2) 0.0286(13) Uani 1 1 d . . . O5 O 0.3972(3) 0.8904(7) 0.1654(2) 0.0273(13) Uani 1 1 d . . . O6 O 0.4021(3) 0.6798(7) 0.1051(2) 0.0283(14) Uani 1 1 d . . . O7 O 0.6736(4) 0.4456(9) 0.1339(3) 0.0522(19) Uani 1 1 d . . . O8 O 0.7448(3) 0.3921(7) 0.2230(2) 0.0312(14) Uani 1 1 d . . . O9 O 0.8692(4) 0.4585(10) 0.3363(3) 0.058(2) Uani 1 1 d . . . O10A O 0.9516(8) 0.3832(17) 0.4271(6) 0.037(3) Uiso 0.50 1 d P A 1 O10B O 0.9657(7) 0.4576(16) 0.4153(5) 0.029(3) Uiso 0.50 1 d P B 2 O11 O 0.7644(3) 0.5912(6) 0.3888(2) 0.0223(12) Uani 1 1 d . . . N2 N 0.3613(4) 1.0379(8) 0.4246(3) 0.0225(15) Uani 1 1 d . . . N4 N 0.3104(4) 0.7396(9) 0.2351(3) 0.0243(15) Uani 1 1 d . . . N5 N 0.4248(4) 0.7533(9) 0.1528(3) 0.0232(16) Uani 1 1 d . . . N7 N 0.6851(5) 0.4549(9) 0.1878(4) 0.0298(18) Uani 1 1 d . . . N18A N 0.8871(12) 0.444(3) 0.3935(8) 0.037(6) Uiso 0.50 1 d P A 1 N18B N 0.8959(10) 0.498(2) 0.3858(9) 0.026(5) Uiso 0.50 1 d P B 2 N19 N 0.9931(16) 0.755(4) 0.4113(12) 0.128(9) Uiso 0.50 1 d P . . C1 C 0.4748(4) 0.8893(9) 0.3952(3) 0.0198(17) Uani 1 1 d . . . H1 H 0.5082 0.9101 0.4328 0.024 Uiso 1 1 d R . . C2 C 0.3936(4) 0.9382(9) 0.3808(3) 0.0178(17) Uani 1 1 d . . . C3 C 0.3408(4) 0.8960(9) 0.3276(3) 0.0213(18) Uani 1 1 d . . . H3 H 0.2858 0.9249 0.3209 0.026 Uiso 1 1 d R . . C4 C 0.3705(4) 0.8129(9) 0.2859(3) 0.0181(17) Uani 1 1 d . . . C5 C 0.4951(4) 0.6788(9) 0.1969(3) 0.0135(16) Uani 1 1 d . . . C6 C 0.5533(5) 0.5967(9) 0.1741(3) 0.0225(18) Uani 1 1 d . . . H6 H 0.5434 0.5737 0.1337 0.027 Uiso 1 1 d R . . C7 C 0.6252(4) 0.5481(9) 0.2135(3) 0.0184(17) Uani 1 1 d . . . C8 C 0.6439(4) 0.5820(9) 0.2732(3) 0.0188(17) Uani 1 1 d . . . H8 H 0.6941 0.5518 0.2978 0.023 Uiso 1 1 d R . . C9 C 0.5871(4) 0.7318(9) 0.3559(3) 0.0162(17) Uani 1 1 d . . . C10 C 0.5050(4) 0.8056(8) 0.3522(3) 0.0139(16) Uani 1 1 d . . . C11 C 0.4553(4) 0.7760(9) 0.2953(3) 0.0142(16) Uani 1 1 d . . . C12 C 0.5060(4) 0.7071(9) 0.2578(3) 0.0147(17) Uani 1 1 d . . . C13 C 0.5842(4) 0.6679(9) 0.2959(3) 0.0151(17) Uani 1 1 d . . . C14 C 0.6449(4) 0.7368(9) 0.4082(3) 0.0177(17) Uani 1 1 d . . . H14 H 0.6271 0.7924 0.4383 0.021 Uiso 1 1 d R . . C15 C 0.7256(4) 0.6783(9) 0.4268(3) 0.0169(17) Uani 1 1 d . . . C16 C 0.7795(4) 0.6959(10) 0.4815(3) 0.0204(18) Uani 1 1 d . . . H16 H 0.7695 0.7502 0.5148 0.024 Uiso 1 1 d R . . C17 C 0.8538(5) 0.6149(10) 0.4779(4) 0.030(2) Uani 1 1 d . A . H17 H 0.9015 0.6039 0.5077 0.035 Uiso 1 1 d R . . C18 C 0.8402(4) 0.5575(10) 0.4221(4) 0.029(2) Uani 1 1 d . . . C19 C 1.002(2) 0.848(5) 0.4537(16) 0.130(12) Uiso 0.50 1 d P . . C20 C 1.016(3) 0.974(6) 0.506(2) 0.115(13) Uiso 0.50 1 d P . . C21 C 0.6191(6) 0.2678(11) 0.4226(4) 0.040(2) Uani 1 1 d . . . C22 C 0.7349(6) 0.2840(11) 0.5205(4) 0.045(2) Uani 1 1 d . . . C23 C 0.6692(7) 0.3740(11) 0.5318(4) 0.050(3) Uani 1 1 d . . . C24 C 0.5770(5) 0.2493(11) 0.3658(4) 0.036(2) Uani 1 1 d . . . C25 C 0.5305(7) 0.1788(12) 0.2539(5) 0.053(3) Uani 1 1 d . . . H25 H 0.5293 0.1393 0.2158 0.063 Uiso 1 1 d R . . C26 C 0.4663(6) 0.2568(12) 0.2665(4) 0.046(3) Uani 1 1 d . . . H26 H 0.4195 0.2798 0.2368 0.055 Uiso 1 1 d R . . C27 C 0.8154(6) 0.2613(14) 0.5613(5) 0.062(3) Uani 1 1 d . . . H271 H 0.8553 0.3061 0.5419 0.093 Uiso 1 1 d R . . H272 H 0.8265 0.1416 0.5705 0.093 Uiso 1 1 d R . . H273 H 0.8183 0.3242 0.5974 0.093 Uiso 1 1 d R . . C28 C 0.6705(7) 0.4744(12) 0.5867(5) 0.065(3) Uani 1 1 d . . . H281 H 0.7220 0.4621 0.6153 0.098 Uiso 1 1 d R . . H282 H 0.6276 0.4324 0.6037 0.098 Uiso 1 1 d R . . H283 H 0.6612 0.5940 0.5766 0.098 Uiso 1 1 d 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 0.0424(15) 0.0364(14) 0.0557(17) 0.0037(13) 0.0131(13) 0.0069(11) S2 0.0547(16) 0.0344(14) 0.0578(17) 0.0065(12) 0.0275(13) 0.0093(11) S3 0.0518(15) 0.0332(13) 0.0511(15) 0.0026(11) 0.0268(13) -0.0014(11) S4 0.0378(14) 0.0344(14) 0.0657(17) 0.0125(12) 0.0206(13) 0.0004(11) O1 0.026(3) 0.052(4) 0.020(3) -0.014(3) -0.006(3) 0.012(3) O2 0.013(3) 0.036(3) 0.029(3) -0.003(3) 0.008(2) 0.010(2) O3 0.021(3) 0.070(5) 0.034(4) -0.012(3) -0.004(3) 0.012(3) O4 0.026(3) 0.032(3) 0.027(3) -0.011(3) 0.005(3) -0.004(3) O5 0.024(3) 0.032(3) 0.025(3) -0.002(3) 0.005(2) 0.005(3) O6 0.030(3) 0.039(3) 0.017(3) -0.004(3) 0.008(3) -0.006(3) O7 0.060(4) 0.077(5) 0.022(4) -0.003(3) 0.014(3) 0.031(4) O8 0.023(3) 0.041(4) 0.029(3) -0.006(3) 0.004(3) 0.010(3) O9 0.041(4) 0.087(5) 0.041(4) -0.023(4) 0.000(3) 0.027(4) O11 0.016(3) 0.028(3) 0.021(3) -0.004(2) 0.000(2) 0.004(2) N2 0.023(4) 0.025(4) 0.020(4) 0.003(3) 0.008(3) 0.005(3) N4 0.011(4) 0.044(4) 0.016(3) -0.008(3) 0.000(3) -0.002(3) N5 0.028(4) 0.031(4) 0.011(4) 0.000(3) 0.004(3) -0.010(3) N7 0.031(4) 0.029(4) 0.031(5) -0.007(4) 0.010(3) 0.003(4) C1 0.021(4) 0.018(4) 0.017(4) 0.000(3) -0.002(3) -0.004(3) C2 0.020(4) 0.017(4) 0.018(4) -0.001(3) 0.008(3) -0.002(3) C3 0.019(4) 0.022(4) 0.023(4) 0.004(4) 0.006(4) 0.000(3) C4 0.016(4) 0.019(4) 0.014(4) 0.000(3) -0.005(3) -0.003(3) C5 0.006(4) 0.020(4) 0.011(4) 0.006(3) -0.004(3) -0.001(3) C6 0.030(5) 0.019(4) 0.019(4) -0.002(3) 0.008(4) 0.005(4) C7 0.023(4) 0.013(4) 0.020(4) -0.001(3) 0.008(4) 0.001(3) C8 0.018(4) 0.019(4) 0.020(4) 0.000(3) 0.006(3) -0.005(3) C9 0.018(4) 0.012(4) 0.016(4) 0.002(3) -0.001(3) 0.003(3) C10 0.016(4) 0.016(4) 0.010(4) 0.005(3) 0.005(3) -0.002(3) C11 0.008(4) 0.018(4) 0.019(4) 0.004(3) 0.008(3) -0.001(3) C12 0.005(4) 0.017(4) 0.022(4) 0.004(3) 0.004(3) -0.004(3) C13 0.014(4) 0.013(4) 0.018(4) 0.000(3) 0.004(3) -0.005(3) C14 0.015(4) 0.015(4) 0.025(4) 0.003(3) 0.008(3) 0.003(3) C15 0.017(4) 0.015(4) 0.019(4) 0.000(3) 0.007(3) -0.001(3) C16 0.013(4) 0.026(5) 0.020(5) -0.004(4) -0.001(4) -0.001(3) C17 0.023(5) 0.033(5) 0.028(5) -0.008(4) -0.002(4) 0.005(4) C18 0.017(4) 0.032(5) 0.033(5) -0.008(4) -0.005(4) 0.007(4) C21 0.050(6) 0.023(5) 0.049(7) 0.012(5) 0.020(5) 0.003(4) C22 0.053(6) 0.023(5) 0.053(6) 0.005(5) 0.003(5) -0.005(5) C23 0.089(8) 0.014(5) 0.049(6) 0.002(4) 0.023(6) -0.004(5) C24 0.038(6) 0.014(4) 0.059(7) 0.007(5) 0.018(5) 0.001(4) C25 0.073(8) 0.038(6) 0.051(7) 0.005(5) 0.023(6) -0.017(5) C26 0.048(7) 0.031(5) 0.055(7) -0.002(5) 0.006(5) -0.013(5) C27 0.064(8) 0.044(6) 0.066(8) 0.007(6) -0.008(6) -0.004(6) C28 0.103(9) 0.031(6) 0.071(8) 0.002(6) 0.035(7) -0.011(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 S1 C22 1.748(10) . ? S1 C21 1.753(9) . ? S2 C23 1.736(11) . ? S2 C21 1.766(9) . ? S3 C25 1.725(11) . ? S3 C24 1.762(9) . ? S4 C26 1.747(10) . ? S4 C24 1.778(9) . ? O1 N2 1.229(7) . ? O2 N2 1.235(7) . ? O3 N4 1.213(7) . ? O4 N4 1.246(8) . ? O5 N5 1.223(8) . ? O6 N5 1.221(8) . ? O7 N7 1.221(9) . ? O8 N7 1.234(9) . ? O9 N18B 1.170(19) . ? O9 N18A 1.293(19) . ? O10A N18A 1.27(2) . ? O10B N18B 1.25(2) . ? O11 C18 1.351(8) . ? O11 C15 1.394(8) . ? N2 C2 1.483(9) . ? N4 C4 1.470(9) . ? N5 C5 1.484(9) . ? N7 C7 1.480(10) . ? N18A C18 1.45(2) . ? N18B C18 1.477(18) . ? N19 C19 1.20(4) . ? C1 C2 1.383(10) . ? C1 C10 1.388(10) . ? C2 C3 1.374(10) . ? C3 C4 1.357(10) . ? C4 C11 1.423(9) . ? C5 C6 1.377(10) . ? C5 C12 1.397(10) . ? C6 C7 1.382(10) . ? C7 C8 1.370(10) . ? C8 C13 1.412(10) . ? C9 C14 1.361(10) . ? C9 C13 1.467(10) . ? C9 C10 1.481(9) . ? C10 C11 1.401(9) . ? C11 C12 1.462(9) . ? C12 C13 1.433(10) . ? C14 C15 1.400(9) . ? C15 C16 1.378(10) . ? C16 C17 1.422(10) . ? C17 C18 1.336(11) . ? C19 C20 1.53(6) . ? C19 C20 1.74(7) 3_776 ? C20 C20 0.67(8) 3_776 ? C20 C19 1.74(7) 3_776 ? C21 C24 1.346(13) . ? C22 C23 1.388(13) . ? C22 C27 1.468(13) . ? C23 C28 1.488(13) . ? C25 C26 1.334(13) . ? 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 C22 S1 C21 96.6(4) . . ? C23 S2 C21 96.0(5) . . ? C25 S3 C24 95.6(5) . . ? C26 S4 C24 94.7(5) . . ? N18B O9 N18A 22.3(11) . . ? C18 O11 C15 104.8(5) . . ? O1 N2 O2 124.6(6) . . ? O1 N2 C2 117.6(6) . . ? O2 N2 C2 117.8(6) . . ? O3 N4 O4 123.8(6) . . ? O3 N4 C4 119.5(6) . . ? O4 N4 C4 116.6(6) . . ? O6 N5 O5 124.6(7) . . ? O6 N5 C5 117.8(7) . . ? O5 N5 C5 117.5(6) . . ? O7 N7 O8 123.9(7) . . ? O7 N7 C7 119.0(7) . . ? O8 N7 C7 117.1(7) . . ? O10A N18A O9 128.0(16) . . ? O10A N18A C18 115.3(15) . . ? O9 N18A C18 113.7(15) . . ? O9 N18B O10B 123.9(15) . . ? O9 N18B C18 119.7(14) . . ? O10B N18B C18 114.3(16) . . ? C2 C1 C10 117.9(7) . . ? C3 C2 C1 122.8(7) . . ? C3 C2 N2 118.3(6) . . ? C1 C2 N2 118.9(6) . . ? C4 C3 C2 118.8(7) . . ? C3 C4 C11 121.2(6) . . ? C3 C4 N4 116.9(6) . . ? C11 C4 N4 121.2(6) . . ? C6 C5 C12 121.9(6) . . ? C6 C5 N5 116.2(6) . . ? C12 C5 N5 121.5(6) . . ? C5 C6 C7 117.7(7) . . ? C8 C7 C6 124.5(7) . . ? C8 C7 N7 119.1(7) . . ? C6 C7 N7 116.3(7) . . ? C7 C8 C13 117.2(7) . . ? C14 C9 C13 135.0(7) . . ? C14 C9 C10 120.0(6) . . ? C13 C9 C10 105.0(6) . . ? C1 C10 C11 121.0(6) . . ? C1 C10 C9 129.7(6) . . ? C11 C10 C9 109.3(6) . . ? C10 C11 C4 117.6(6) . . ? C10 C11 C12 108.5(6) . . ? C4 C11 C12 134.0(6) . . ? C5 C12 C13 117.9(6) . . ? C5 C12 C11 135.0(6) . . ? C13 C12 C11 107.1(6) . . ? C8 C13 C12 120.1(6) . . ? C8 C13 C9 130.6(7) . . ? C12 C13 C9 109.2(6) . . ? C9 C14 C15 134.3(7) . . ? C16 C15 O11 108.9(6) . . ? C16 C15 C14 128.9(7) . . ? O11 C15 C14 122.2(6) . . ? C15 C16 C17 107.3(7) . . ? C18 C17 C16 104.9(7) . . ? C17 C18 O11 114.0(7) . . ? C17 C18 N18A 131.5(10) . . ? O11 C18 N18A 113.7(10) . . ? C17 C18 N18B 132.3(10) . . ? O11 C18 N18B 112.2(10) . . ? N18A C18 N18B 19.3(10) . . ? N19 C19 C20 177(4) . . ? N19 C19 C20 156(4) . 3_776 ? C20 C19 C20 23(3) . 3_776 ? C20 C20 C19 96(10) 3_776 . ? C20 C20 C19 61(8) 3_776 3_776 ? C19 C20 C19 157(3) . 3_776 ? C24 C21 S1 123.6(7) . . ? C24 C21 S2 122.8(7) . . ? S1 C21 S2 113.6(6) . . ? C23 C22 C27 126.5(10) . . ? C23 C22 S1 115.7(7) . . ? C27 C22 S1 117.8(8) . . ? C22 C23 C28 125.3(10) . . ? C22 C23 S2 117.4(7) . . ? C28 C23 S2 117.3(8) . . ? C21 C24 S3 123.7(7) . . ? C21 C24 S4 122.6(7) . . ? S3 C24 S4 113.7(6) . . ? C26 C25 S3 118.2(8) . . ? C25 C26 S4 117.8(8) . . ? 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 C13 C9 C14 C15 -2.1(15) . . . . ? C9 C14 C15 O11 -0.8(12) . . . . ? _diffrn_measured_fraction_theta_max 0.716 _diffrn_reflns_theta_full 24.92 _diffrn_measured_fraction_theta_full 0.716 _refine_diff_density_max 0.465 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.097 #============================================END