# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Dr Alain Favre-Reguillon' _publ_contact_author_address ; Laboratoire de Catalyse et Synthese Organique - CPE Universite Claude Bernard Lyon1 43, bld du 11 Novembre 1918 Villeurbanne 69622 FRANCE ; _publ_contact_author_email ALAIN.FAVRE-REGUILLON@UNIV-LYON1.FR #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Ultra-deep desulfurization of transportation fuels via charge-transfer complexes under ambient conditions ; #=============================================================================== # TEXT _publ_section_abstract ; New electron acceptors of the flurenone series have been prepared. ; loop_ _publ_author_name 'Alain Favre-Reguillon' 'Rene Faure' 'Marc Lemaire' 'Mathieu Macaud' 'Muriel Rocault' ; J.Schulz ; 'Marc Sevignon' 'M. Vrinat' data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 253625' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4,5-dicyano-2,7-dinitrofluorenone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H4 N4 O5' _chemical_formula_weight 320.22 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' O O 0.0106 0.0060 '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 'P 21/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 14.1690(8) _cell_length_b 6.4510(4) _cell_length_c 15.2380(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.614(2) _cell_angle_gamma 90.00 _cell_volume 1303.64(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8294 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9331 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details 'Multiscan, sortav blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5902 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.69 _reflns_number_total 2562 _reflns_number_gt 1680 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement KappaCCD _computing_data_reduction 'Denzo, Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v 5.03' _computing_structure_refinement 'SHELXTL v 5.03' _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^)+(0.0772P)^2^+0.1903P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2562 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1553 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C1 C 0.82423(17) 0.1210(3) 0.00116(15) 0.0470(6) Uani 1 1 d . . . H1 H 0.8628 0.0294 -0.0166 0.049(6) Uiso 1 1 d R . . C2 C 0.72213(17) 0.0969(3) -0.02220(16) 0.0482(6) Uani 1 1 d . . . C3 C 0.66353(17) 0.2377(4) 0.00273(16) 0.0506(6) Uani 1 1 d . . . H3 H 0.5920 0.2183 -0.0152 0.050 Uiso 1 1 d R . . C4 C 0.70777(16) 0.4109(4) 0.05491(15) 0.0456(5) Uani 1 1 d . . . C4A C 0.81156(15) 0.4407(3) 0.08165(14) 0.0397(5) Uani 1 1 d . . . C4B C 0.88321(14) 0.6044(3) 0.13413(14) 0.0379(5) Uani 1 1 d . . . C5 C 0.87455(15) 0.7814(3) 0.18223(14) 0.0411(5) Uani 1 1 d . . . C6 C 0.95909(17) 0.9092(3) 0.22026(16) 0.0458(5) Uani 1 1 d . . . H6 H 0.9550 1.0327 0.2539 0.050 Uiso 1 1 d R . . C7 C 1.04927(16) 0.8599(3) 0.21071(15) 0.0458(5) Uani 1 1 d . . . C8 C 1.06200(16) 0.6811(4) 0.16816(15) 0.0458(5) Uani 1 1 d . . . H8 H 1.1273 0.6494 0.1660 0.050 Uiso 1 1 d R . . C8A C 0.97911(15) 0.5573(3) 0.13106(15) 0.0413(5) Uani 1 1 d . . . C9 C 0.97380(16) 0.3593(3) 0.08141(15) 0.0449(5) Uani 1 1 d . . . C9A C 0.86685(15) 0.2926(3) 0.05206(15) 0.0411(5) Uani 1 1 d . . . C10 C 0.63854(18) 0.5519(4) 0.0735(2) 0.0652(8) Uani 1 1 d . . . C11 C 0.78622(17) 0.8486(4) 0.19904(17) 0.0517(6) Uani 1 1 d . . . N1 N 0.67167(18) -0.0825(3) -0.07650(15) 0.0637(6) Uani 1 1 d . . . N2 N 0.57667(18) 0.6512(5) 0.0822(2) 0.1118(13) Uani 1 1 d . . . N3 N 0.72158(18) 0.9173(4) 0.21731(19) 0.0828(8) Uani 1 1 d . . . N4 N 1.13444(16) 1.0025(4) 0.24930(15) 0.0576(6) Uani 1 1 d . . . O1 O 1.04235(12) 0.2702(3) 0.06702(13) 0.0609(5) Uani 1 1 d . . . O2 O 0.72423(17) -0.2256(3) -0.08253(16) 0.0848(7) Uani 1 1 d . . . O3 O 0.58015(17) -0.0784(4) -0.11268(18) 0.0991(8) Uani 1 1 d . . . O4 O 1.12292(16) 1.1523(4) 0.29263(16) 0.0840(7) Uani 1 1 d . . . O5 O 1.21123(14) 0.9641(3) 0.23362(16) 0.0785(6) 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 0.0552(13) 0.0444(13) 0.0431(13) -0.0010(10) 0.0196(10) 0.0070(10) C2 0.0580(14) 0.0417(13) 0.0401(13) -0.0016(10) 0.0112(10) -0.0024(10) C3 0.0431(12) 0.0564(15) 0.0460(14) -0.0030(11) 0.0079(10) -0.0023(10) C4 0.0421(12) 0.0505(14) 0.0430(13) -0.0017(10) 0.0133(10) 0.0029(9) C4A 0.0423(12) 0.0412(12) 0.0354(11) 0.0042(9) 0.0136(9) 0.0049(8) C4B 0.0375(11) 0.0401(12) 0.0365(11) 0.0033(9) 0.0137(8) 0.0032(8) C5 0.0429(12) 0.0410(12) 0.0385(12) 0.0022(9) 0.0130(9) 0.0053(9) C6 0.0524(13) 0.0410(13) 0.0423(12) 0.0007(10) 0.0144(10) 0.0000(9) C7 0.0437(12) 0.0474(14) 0.0419(12) 0.0030(10) 0.0096(9) -0.0056(10) C8 0.0382(11) 0.0552(14) 0.0437(13) 0.0042(10) 0.0142(9) 0.0025(9) C8A 0.0391(12) 0.0427(12) 0.0421(12) 0.0029(9) 0.0143(9) 0.0040(9) C9 0.0439(12) 0.0482(13) 0.0445(13) 0.0040(10) 0.0181(10) 0.0084(10) C9A 0.0445(12) 0.0406(12) 0.0387(12) 0.0034(9) 0.0154(9) 0.0046(9) C10 0.0399(14) 0.0732(19) 0.0733(18) -0.0249(14) 0.0086(12) -0.0001(12) C11 0.0471(13) 0.0498(14) 0.0581(15) -0.0108(11) 0.0184(11) 0.0012(10) N1 0.0728(16) 0.0549(15) 0.0591(14) -0.0101(10) 0.0177(11) -0.0107(11) N2 0.0425(13) 0.135(3) 0.139(3) -0.077(2) 0.0086(14) 0.0121(15) N3 0.0606(15) 0.0950(19) 0.0942(19) -0.0374(15) 0.0292(13) 0.0042(13) N4 0.0542(13) 0.0584(14) 0.0550(13) 0.0020(11) 0.0126(10) -0.0108(10) O1 0.0521(10) 0.0612(11) 0.0745(12) -0.0059(9) 0.0286(8) 0.0131(8) O2 0.0968(16) 0.0533(12) 0.1043(18) -0.0247(11) 0.0355(13) -0.0058(10) O3 0.0726(15) 0.0967(18) 0.1074(19) -0.0418(14) 0.0060(13) -0.0182(12) O4 0.0917(15) 0.0796(15) 0.0848(15) -0.0335(12) 0.0360(12) -0.0333(11) O5 0.0480(11) 0.0765(13) 0.1068(17) -0.0042(12) 0.0221(11) -0.0149(9) _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 C9A 1.364(3) . ? C1 C2 1.371(3) . ? C1 H1 0.9081 . ? C2 C3 1.371(3) . ? C2 N1 1.456(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9601 . ? C4 C4A 1.394(3) . ? C4 C10 1.437(3) . ? C4A C9A 1.407(3) . ? C4A C4B 1.488(3) . ? C4B C5 1.386(3) . ? C4B C8A 1.409(3) . ? C5 C6 1.401(3) . ? C5 C11 1.430(3) . ? C6 C7 1.373(3) . ? C6 H6 0.9600 . ? C7 C8 1.366(3) . ? C7 N4 1.466(3) . ? C8 C8A 1.367(3) . ? C8 H8 0.9601 . ? C8A C9 1.473(3) . ? C9 O1 1.213(3) . ? C9 C9A 1.485(3) . ? C10 N2 1.131(3) . ? C11 N3 1.137(3) . ? N1 O2 1.210(3) . ? N1 O3 1.218(3) . ? N4 O4 1.213(3) . ? N4 O5 1.219(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 C9A C1 C2 117.0(2) . . ? C9A C1 H1 120.3 . . ? C2 C1 H1 122.6 . . ? C3 C2 C1 122.6(2) . . ? C3 C2 N1 117.4(2) . . ? C1 C2 N1 120.0(2) . . ? C2 C3 C4 119.8(2) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 119.1 . . ? C3 C4 C4A 119.7(2) . . ? C3 C4 C10 114.9(2) . . ? C4A C4 C10 125.3(2) . . ? C4 C4A C9A 117.51(19) . . ? C4 C4A C4B 134.82(19) . . ? C9A C4A C4B 107.62(18) . . ? C5 C4B C8A 117.46(19) . . ? C5 C4B C4A 134.32(18) . . ? C8A C4B C4A 108.23(17) . . ? C4B C5 C6 118.81(19) . . ? C4B C5 C11 126.2(2) . . ? C6 C5 C11 115.0(2) . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 120.4 . . ? C8 C7 C6 121.9(2) . . ? C8 C7 N4 119.5(2) . . ? C6 C7 N4 118.5(2) . . ? C7 C8 C8A 116.9(2) . . ? C7 C8 H8 119.1 . . ? C8A C8 H8 124.0 . . ? C8 C8A C4B 124.0(2) . . ? C8 C8A C9 126.87(19) . . ? C4B C8A C9 109.17(18) . . ? O1 C9 C8A 127.2(2) . . ? O1 C9 C9A 127.2(2) . . ? C8A C9 C9A 105.57(17) . . ? C1 C9A C4A 123.25(19) . . ? C1 C9A C9 127.37(19) . . ? C4A C9A C9 109.33(19) . . ? N2 C10 C4 173.2(3) . . ? N3 C11 C5 173.3(3) . . ? O2 N1 O3 124.6(2) . . ? O2 N1 C2 117.2(2) . . ? O3 N1 C2 118.1(2) . . ? O4 N4 O5 124.7(2) . . ? O4 N4 C7 117.9(2) . . ? O5 N4 C7 117.3(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 C9A C1 C2 C3 0.6(3) . . . . ? C9A C1 C2 N1 180.0(2) . . . . ? C1 C2 C3 C4 -1.0(4) . . . . ? N1 C2 C3 C4 179.6(2) . . . . ? C2 C3 C4 C4A 0.0(3) . . . . ? C2 C3 C4 C10 177.4(2) . . . . ? C3 C4 C4A C9A 1.3(3) . . . . ? C10 C4 C4A C9A -175.9(2) . . . . ? C3 C4 C4A C4B 178.4(2) . . . . ? C10 C4 C4A C4B 1.2(4) . . . . ? C4 C4A C4B C5 5.8(4) . . . . ? C9A C4A C4B C5 -176.9(2) . . . . ? C4 C4A C4B C8A -174.3(2) . . . . ? C9A C4A C4B C8A 2.9(2) . . . . ? C8A C4B C5 C6 3.6(3) . . . . ? C4A C4B C5 C6 -176.6(2) . . . . ? C8A C4B C5 C11 -175.4(2) . . . . ? C4A C4B C5 C11 4.4(4) . . . . ? C4B C5 C6 C7 -0.4(3) . . . . ? C11 C5 C6 C7 178.7(2) . . . . ? C5 C6 C7 C8 -3.2(3) . . . . ? C5 C6 C7 N4 178.1(2) . . . . ? C6 C7 C8 C8A 3.2(3) . . . . ? N4 C7 C8 C8A -178.11(19) . . . . ? C7 C8 C8A C4B 0.3(3) . . . . ? C7 C8 C8A C9 179.4(2) . . . . ? C5 C4B C8A C8 -3.6(3) . . . . ? C4A C4B C8A C8 176.5(2) . . . . ? C5 C4B C8A C9 177.08(19) . . . . ? C4A C4B C8A C9 -2.8(2) . . . . ? C8 C8A C9 O1 2.0(4) . . . . ? C4B C8A C9 O1 -178.8(2) . . . . ? C8 C8A C9 C9A -177.6(2) . . . . ? C4B C8A C9 C9A 1.6(2) . . . . ? C2 C1 C9A C4A 0.8(3) . . . . ? C2 C1 C9A C9 -176.4(2) . . . . ? C4 C4A C9A C1 -1.7(3) . . . . ? C4B C4A C9A C1 -179.5(2) . . . . ? C4 C4A C9A C9 175.90(18) . . . . ? C4B C4A C9A C9 -1.9(2) . . . . ? O1 C9 C9A C1 -1.8(4) . . . . ? C8A C9 C9A C1 177.7(2) . . . . ? O1 C9 C9A C4A -179.3(2) . . . . ? C8A C9 C9A C4A 0.3(2) . . . . ? C3 C4 C10 N2 -8(3) . . . . ? C4A C4 C10 N2 170(3) . . . . ? C4B C5 C11 N3 177(2) . . . . ? C6 C5 C11 N3 -2(3) . . . . ? C3 C2 N1 O2 -165.6(2) . . . . ? C1 C2 N1 O2 15.0(3) . . . . ? C3 C2 N1 O3 14.5(4) . . . . ? C1 C2 N1 O3 -164.8(2) . . . . ? C8 C7 N4 O4 -174.7(2) . . . . ? C6 C7 N4 O4 4.0(3) . . . . ? C8 C7 N4 O5 6.9(3) . . . . ? C6 C7 N4 O5 -174.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.838 _diffrn_reflns_theta_full 27.69 _diffrn_measured_fraction_theta_full 0.838 _refine_diff_density_max 0.180 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.045 data_compound_4-1 _database_code_depnum_ccdc_archive 'CCDC 253626' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H16 N4 O5 S' _chemical_formula_weight 532.52 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' O O 0.0106 0.0060 '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' 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 'P 21 / 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 7.7310(4) _cell_length_b 15.1430(9) _cell_length_c 21.1520(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.189(2) _cell_angle_gamma 90.00 _cell_volume 2451.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9128 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 24.407 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8755 _exptl_absorpt_correction_T_max 0.9909 _exptl_absorpt_process_details 'Multiscan, sortav blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method kappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13094 _diffrn_reflns_av_R_equivalents 0.1348 _diffrn_reflns_av_sigmaI/netI 0.1116 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.39 _reflns_number_total 3983 _reflns_number_gt 2033 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement kappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor,1997)' _computing_structure_solution 'SHELXTL v 5.03' _computing_structure_refinement 'SHELXTL v 5.03' _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^)+(0.1019P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3983 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1471 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.2079 _refine_ls_wR_factor_gt 0.1599 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.003 _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 0.4124(6) 0.2860(3) 0.7640(2) 0.0469(13) Uani 1 1 d . . . H1 H 0.4415 0.2391 0.7920 0.056 Uiso 1 1 calc R . . C2 C 0.4668(6) 0.3716(3) 0.7794(2) 0.0439(12) Uani 1 1 d . . . C3 C 0.4156(6) 0.4415(3) 0.7407(2) 0.0503(13) Uani 1 1 d . . . H3 H 0.4478 0.4984 0.7540 0.060 Uiso 1 1 calc R . . C4 C 0.3154(6) 0.4283(3) 0.6813(2) 0.0441(12) Uani 1 1 d . . . C4A C 0.2664(6) 0.3421(3) 0.6619(2) 0.0387(11) Uani 1 1 d . . . C4B C 0.1630(5) 0.3040(3) 0.6040(2) 0.0383(11) Uani 1 1 d . . . C5 C 0.1020(6) 0.3364(3) 0.5420(2) 0.0424(11) Uani 1 1 d . . . C6 C -0.0005(6) 0.2815(3) 0.4987(2) 0.0475(12) Uani 1 1 d . . . H6 H -0.0461 0.3028 0.4586 0.057 Uiso 1 1 calc R . . C7 C -0.0341(6) 0.1965(3) 0.5153(2) 0.0450(12) Uani 1 1 d . . . C8 C 0.0333(6) 0.1594(3) 0.5730(2) 0.0436(12) Uani 1 1 d . . . H8 H 0.0143 0.1005 0.5823 0.052 Uiso 1 1 calc R . . C8A C 0.1306(6) 0.2145(3) 0.6162(2) 0.0370(11) Uani 1 1 d . . . C9 C 0.2275(6) 0.1908(3) 0.6799(2) 0.0439(12) Uani 1 1 d . . . C9A C 0.3134(6) 0.2738(3) 0.7055(2) 0.0381(11) Uani 1 1 d . . . C10 C 0.2486(8) 0.5069(4) 0.6464(3) 0.0663(16) Uani 1 1 d . . . C11 C 0.1601(7) 0.4176(4) 0.5177(2) 0.0549(14) Uani 1 1 d . . . N1 N 0.5738(6) 0.3875(4) 0.8416(2) 0.0579(12) Uani 1 1 d . . . N2 N 0.1936(8) 0.5712(3) 0.6243(3) 0.0973(19) Uani 1 1 d . . . N3 N 0.2133(7) 0.4769(4) 0.4930(3) 0.0869(16) Uani 1 1 d . . . N4 N -0.1415(6) 0.1398(4) 0.4679(2) 0.0610(12) Uani 1 1 d . . . O1 O 0.2357(5) 0.1191(2) 0.70520(16) 0.0621(10) Uani 1 1 d . . . O2 O 0.6347(5) 0.3236(3) 0.87213(17) 0.0687(11) Uani 1 1 d . . . O3 O 0.5954(5) 0.4642(3) 0.8595(2) 0.0845(13) Uani 1 1 d . . . O4 O -0.2084(5) 0.1730(3) 0.41817(19) 0.0767(12) Uani 1 1 d . . . O5 O -0.1567(6) 0.0624(3) 0.4822(2) 0.0864(13) Uani 1 1 d . . . S21 S -0.26827(16) 0.16380(9) 0.69260(6) 0.0502(4) Uani 1 1 d . . . C21 C -0.4097(7) 0.3295(4) 0.5506(2) 0.0584(14) Uani 1 1 d . . . H21 H -0.3935 0.3893 0.5431 0.070 Uiso 1 1 calc R . . C22 C -0.5035(8) 0.2782(5) 0.5049(3) 0.0709(17) Uani 1 1 d . . . H22 H -0.5478 0.3033 0.4658 0.085 Uiso 1 1 calc R . . C23 C -0.5342(7) 0.1899(5) 0.5153(3) 0.0686(17) Uani 1 1 d . . . H23 H -0.6012 0.1575 0.4834 0.082 Uiso 1 1 calc R . . C24 C -0.4672(6) 0.1480(3) 0.5724(2) 0.0515(13) Uani 1 1 d . . . C26 C -0.0853(7) 0.2912(4) 0.7702(2) 0.0568(14) Uani 1 1 d . . . C27 C -0.0349(6) 0.3787(4) 0.7779(3) 0.0643(16) Uani 1 1 d . . . H27 H 0.0341 0.3960 0.8155 0.077 Uiso 1 1 calc R . . C28 C -0.0851(8) 0.4419(4) 0.7303(3) 0.0711(17) Uani 1 1 d . . . H28 H -0.0527 0.5006 0.7376 0.085 Uiso 1 1 calc R . . C29 C -0.1801(7) 0.4187(3) 0.6738(3) 0.0581(14) Uani 1 1 d . . . H29 H -0.2073 0.4609 0.6419 0.070 Uiso 1 1 calc R . . C30 C -0.3376(6) 0.2914(3) 0.6091(2) 0.0427(12) Uani 1 1 d . . . C31 C -0.3679(6) 0.2013(3) 0.6190(2) 0.0428(12) Uani 1 1 d . . . C32 C -0.2376(6) 0.3311(3) 0.6633(2) 0.0467(12) Uani 1 1 d . . . C33 C -0.1869(6) 0.2694(3) 0.7124(2) 0.0447(12) Uani 1 1 d . . . C34 C -0.4974(7) 0.0528(4) 0.5852(3) 0.0747(18) Uani 1 1 d . . . H34A H -0.4403 0.0378 0.6271 0.112 Uiso 1 1 calc R . . H34B H -0.4507 0.0172 0.5540 0.112 Uiso 1 1 calc R . . H34C H -0.6206 0.0420 0.5826 0.112 Uiso 1 1 calc R . . C35 C -0.0351(8) 0.2229(4) 0.8207(3) 0.0756(18) Uani 1 1 d . . . H35A H -0.0830 0.1668 0.8061 0.113 Uiso 1 1 calc R . . H35B H -0.0799 0.2395 0.8590 0.113 Uiso 1 1 calc R . . H35C H 0.0900 0.2186 0.8292 0.113 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 C1 0.049(3) 0.052(3) 0.041(3) 0.006(2) 0.012(2) 0.006(2) C2 0.034(3) 0.059(4) 0.038(3) -0.008(3) 0.004(2) 0.000(2) C3 0.058(3) 0.035(3) 0.060(3) -0.011(3) 0.012(3) -0.003(2) C4 0.042(3) 0.039(3) 0.050(3) -0.001(2) 0.002(2) 0.000(2) C4A 0.046(3) 0.037(3) 0.035(3) 0.003(2) 0.011(2) 0.003(2) C4B 0.040(3) 0.038(3) 0.040(3) -0.001(2) 0.016(2) 0.003(2) C5 0.038(3) 0.049(3) 0.041(3) 0.005(2) 0.006(2) 0.005(2) C6 0.044(3) 0.060(4) 0.039(3) 0.006(3) 0.009(2) 0.005(2) C7 0.038(3) 0.050(3) 0.046(3) -0.007(3) 0.004(2) 0.000(2) C8 0.038(3) 0.043(3) 0.051(3) -0.001(3) 0.010(2) -0.005(2) C8A 0.042(3) 0.034(3) 0.037(3) -0.002(2) 0.011(2) -0.002(2) C9 0.051(3) 0.037(3) 0.046(3) 0.002(2) 0.016(2) -0.003(2) C9A 0.042(3) 0.035(3) 0.038(3) -0.002(2) 0.008(2) -0.003(2) C10 0.081(4) 0.037(3) 0.075(4) -0.001(3) -0.010(3) -0.007(3) C11 0.061(4) 0.051(4) 0.051(3) 0.015(3) 0.003(3) 0.005(3) N1 0.051(3) 0.070(4) 0.053(3) -0.010(3) 0.009(2) -0.001(3) N2 0.130(5) 0.044(3) 0.106(4) 0.010(3) -0.023(4) 0.001(3) N3 0.100(4) 0.072(4) 0.090(4) 0.031(3) 0.018(3) -0.004(3) N4 0.050(3) 0.075(4) 0.057(3) -0.013(3) 0.003(2) -0.001(2) O1 0.081(3) 0.043(2) 0.060(2) 0.0096(18) 0.0005(19) -0.0119(18) O2 0.060(2) 0.089(3) 0.053(2) 0.002(2) -0.0052(19) 0.004(2) O3 0.084(3) 0.085(3) 0.077(3) -0.025(3) -0.013(2) -0.009(2) O4 0.059(2) 0.112(4) 0.054(2) -0.006(2) -0.008(2) -0.004(2) O5 0.088(3) 0.072(3) 0.091(3) -0.016(3) -0.014(2) -0.019(2) S21 0.0534(8) 0.0462(8) 0.0507(8) 0.0034(6) 0.0066(6) 0.0016(6) C21 0.055(3) 0.068(4) 0.054(3) 0.007(3) 0.014(3) 0.006(3) C22 0.075(4) 0.092(5) 0.047(3) 0.001(4) 0.012(3) 0.025(4) C23 0.051(3) 0.099(5) 0.054(4) -0.031(4) 0.000(3) 0.009(3) C24 0.038(3) 0.060(4) 0.057(3) -0.017(3) 0.005(2) 0.004(2) C26 0.056(3) 0.064(4) 0.050(3) -0.013(3) 0.008(3) 0.008(3) C27 0.042(3) 0.084(5) 0.067(4) -0.029(4) 0.008(3) -0.007(3) C28 0.070(4) 0.053(4) 0.094(5) -0.021(4) 0.027(4) -0.009(3) C29 0.058(3) 0.050(4) 0.070(4) 0.001(3) 0.021(3) 0.003(3) C30 0.043(3) 0.046(3) 0.039(3) 0.004(2) 0.008(2) 0.004(2) C31 0.033(3) 0.046(3) 0.050(3) -0.004(2) 0.009(2) 0.001(2) C32 0.040(3) 0.044(3) 0.060(3) -0.003(3) 0.021(2) 0.003(2) C33 0.039(3) 0.047(3) 0.049(3) -0.004(3) 0.011(2) 0.008(2) C34 0.064(4) 0.065(4) 0.093(5) -0.031(3) 0.008(3) -0.015(3) C35 0.063(4) 0.102(5) 0.059(4) -0.002(4) 0.000(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9A 1.372(6) . ? C1 C2 1.387(7) . ? C1 H1 0.9300 . ? C2 C3 1.363(6) . ? C2 N1 1.470(6) . ? C3 C4 1.392(6) . ? C3 H3 0.9300 . ? C4 C4A 1.404(6) . ? C4 C10 1.456(8) . ? C4A C9A 1.398(6) . ? C4A C4B 1.482(6) . ? C4B C8A 1.409(6) . ? C4B C5 1.417(6) . ? C5 C6 1.396(6) . ? C5 C11 1.429(7) . ? C6 C7 1.369(6) . ? C6 H6 0.9300 . ? C7 C8 1.377(6) . ? C7 N4 1.482(7) . ? C8 C8A 1.379(6) . ? C8 H8 0.9300 . ? C8A C9 1.490(6) . ? C9 O1 1.209(5) . ? C9 C9A 1.487(6) . ? C10 N2 1.136(7) . ? C11 N3 1.144(6) . ? N1 O2 1.220(5) . ? N1 O3 1.226(6) . ? N4 O4 1.214(6) . ? N4 O5 1.219(6) . ? S21 C31 1.731(5) . ? S21 C33 1.748(5) . ? C21 C22 1.366(8) . ? C21 C30 1.407(7) . ? C21 H21 0.9300 . ? C22 C23 1.381(8) . ? C22 H22 0.9300 . ? C23 C24 1.396(8) . ? C23 H23 0.9300 . ? C24 C31 1.413(7) . ? C24 C34 1.492(7) . ? C26 C27 1.383(8) . ? C26 C33 1.395(7) . ? C26 C35 1.497(7) . ? C27 C28 1.403(8) . ? C27 H27 0.9300 . ? C28 C29 1.357(8) . ? C28 H28 0.9300 . ? C29 C32 1.408(7) . ? C29 H29 0.9300 . ? C30 C31 1.406(6) . ? C30 C32 1.421(7) . ? C32 C33 1.410(7) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9A C1 C2 116.7(4) . . ? C9A C1 H1 121.7 . . ? C2 C1 H1 121.7 . . ? C3 C2 C1 122.2(4) . . ? C3 C2 N1 119.2(5) . . ? C1 C2 N1 118.5(5) . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C4A 119.3(4) . . ? C3 C4 C10 116.8(4) . . ? C4A C4 C10 123.4(4) . . ? C9A C4A C4 117.4(4) . . ? C9A C4A C4B 108.4(4) . . ? C4 C4A C4B 134.1(4) . . ? C8A C4B C5 117.4(4) . . ? C8A C4B C4A 108.2(4) . . ? C5 C4B C4A 134.4(4) . . ? C6 C5 C4B 118.9(4) . . ? C6 C5 C11 117.1(4) . . ? C4B C5 C11 123.4(4) . . ? C7 C6 C5 120.2(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 123.3(4) . . ? C6 C7 N4 118.8(5) . . ? C8 C7 N4 117.9(5) . . ? C7 C8 C8A 116.3(5) . . ? C7 C8 H8 121.9 . . ? C8A C8 H8 121.9 . . ? C8 C8A C4B 123.7(4) . . ? C8 C8A C9 127.6(4) . . ? C4B C8A C9 108.5(4) . . ? O1 C9 C9A 127.3(5) . . ? O1 C9 C8A 127.2(4) . . ? C9A C9 C8A 105.5(4) . . ? C1 C9A C4A 123.7(4) . . ? C1 C9A C9 127.2(4) . . ? C4A C9A C9 109.0(4) . . ? N2 C10 C4 173.8(6) . . ? N3 C11 C5 172.2(6) . . ? O2 N1 O3 124.2(5) . . ? O2 N1 C2 117.9(5) . . ? O3 N1 C2 117.9(5) . . ? O4 N4 O5 124.7(5) . . ? O4 N4 C7 118.3(5) . . ? O5 N4 C7 117.0(5) . . ? C31 S21 C33 90.8(2) . . ? C22 C21 C30 119.5(5) . . ? C22 C21 H21 120.2 . . ? C30 C21 H21 120.2 . . ? C21 C22 C23 121.6(6) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C22 C23 C24 121.8(5) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C23 C24 C31 116.2(5) . . ? C23 C24 C34 123.3(5) . . ? C31 C24 C34 120.5(5) . . ? C27 C26 C33 116.3(5) . . ? C27 C26 C35 122.6(5) . . ? C33 C26 C35 121.2(5) . . ? C26 C27 C28 121.7(5) . . ? C26 C27 H27 119.2 . . ? C28 C27 H27 119.2 . . ? C29 C28 C27 121.0(5) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C32 120.1(5) . . ? C28 C29 H29 120.0 . . ? C32 C29 H29 120.0 . . ? C31 C30 C21 118.4(5) . . ? C31 C30 C32 111.9(4) . . ? C21 C30 C32 129.7(5) . . ? C30 C31 C24 122.4(5) . . ? C30 C31 S21 112.9(3) . . ? C24 C31 S21 124.7(4) . . ? C29 C32 C33 117.4(5) . . ? C29 C32 C30 130.4(5) . . ? C33 C32 C30 112.2(4) . . ? C26 C33 C32 123.5(5) . . ? C26 C33 S21 124.4(4) . . ? C32 C33 S21 112.1(4) . . ? C24 C34 H34A 109.5 . . ? C24 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C24 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C26 C35 H35A 109.5 . . ? C26 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C26 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 4.4(6) . . . . ? C9A C1 C2 N1 -179.7(4) . . . . ? C1 C2 C3 C4 -4.6(7) . . . . ? N1 C2 C3 C4 179.5(4) . . . . ? C2 C3 C4 C4A 0.5(7) . . . . ? C2 C3 C4 C10 172.8(4) . . . . ? C3 C4 C4A C9A 3.6(6) . . . . ? C10 C4 C4A C9A -168.2(4) . . . . ? C3 C4 C4A C4B 179.8(4) . . . . ? C10 C4 C4A C4B 8.0(8) . . . . ? C9A C4A C4B C8A 7.0(5) . . . . ? C4 C4A C4B C8A -169.4(5) . . . . ? C9A C4A C4B C5 -169.5(4) . . . . ? C4 C4A C4B C5 14.1(8) . . . . ? C8A C4B C5 C6 6.2(6) . . . . ? C4A C4B C5 C6 -177.6(4) . . . . ? C8A C4B C5 C11 -164.3(4) . . . . ? C4A C4B C5 C11 12.0(7) . . . . ? C4B C5 C6 C7 -3.0(6) . . . . ? C11 C5 C6 C7 168.0(4) . . . . ? C5 C6 C7 C8 -2.2(7) . . . . ? C5 C6 C7 N4 -179.2(4) . . . . ? C6 C7 C8 C8A 3.8(7) . . . . ? N4 C7 C8 C8A -179.1(4) . . . . ? C7 C8 C8A C4B -0.2(6) . . . . ? C7 C8 C8A C9 -175.8(4) . . . . ? C5 C4B C8A C8 -4.7(6) . . . . ? C4A C4B C8A C8 178.1(4) . . . . ? C5 C4B C8A C9 171.6(3) . . . . ? C4A C4B C8A C9 -5.6(5) . . . . ? C8 C8A C9 O1 -1.1(8) . . . . ? C4B C8A C9 O1 -177.1(4) . . . . ? C8 C8A C9 C9A 178.3(4) . . . . ? C4B C8A C9 C9A 2.3(5) . . . . ? C2 C1 C9A C4A 0.0(6) . . . . ? C2 C1 C9A C9 -174.6(4) . . . . ? C4 C4A C9A C1 -3.9(6) . . . . ? C4B C4A C9A C1 179.0(4) . . . . ? C4 C4A C9A C9 171.6(4) . . . . ? C4B C4A C9A C9 -5.5(5) . . . . ? O1 C9 C9A C1 -3.2(8) . . . . ? C8A C9 C9A C1 177.4(4) . . . . ? O1 C9 C9A C4A -178.5(4) . . . . ? C8A C9 C9A C4A 2.1(5) . . . . ? C3 C4 C10 N2 -40(6) . . . . ? C4A C4 C10 N2 132(6) . . . . ? C6 C5 C11 N3 -51(4) . . . . ? C4B C5 C11 N3 119(4) . . . . ? C3 C2 N1 O2 -171.7(4) . . . . ? C1 C2 N1 O2 12.2(6) . . . . ? C3 C2 N1 O3 8.6(6) . . . . ? C1 C2 N1 O3 -167.5(4) . . . . ? C6 C7 N4 O4 -6.3(6) . . . . ? C8 C7 N4 O4 176.5(4) . . . . ? C6 C7 N4 O5 174.0(4) . . . . ? C8 C7 N4 O5 -3.2(6) . . . . ? C30 C21 C22 C23 1.9(8) . . . . ? C21 C22 C23 C24 -1.7(8) . . . . ? C22 C23 C24 C31 0.6(7) . . . . ? C22 C23 C24 C34 -179.9(5) . . . . ? C33 C26 C27 C28 0.7(7) . . . . ? C35 C26 C27 C28 -179.3(5) . . . . ? C26 C27 C28 C29 -2.5(8) . . . . ? C27 C28 C29 C32 3.3(8) . . . . ? C22 C21 C30 C31 -1.2(7) . . . . ? C22 C21 C30 C32 -179.4(5) . . . . ? C21 C30 C31 C24 0.1(6) . . . . ? C32 C30 C31 C24 178.7(4) . . . . ? C21 C30 C31 S21 179.1(3) . . . . ? C32 C30 C31 S21 -2.3(5) . . . . ? C23 C24 C31 C30 0.2(6) . . . . ? C34 C24 C31 C30 -179.4(4) . . . . ? C23 C24 C31 S21 -178.7(3) . . . . ? C34 C24 C31 S21 1.8(6) . . . . ? C33 S21 C31 C30 1.1(3) . . . . ? C33 S21 C31 C24 180.0(4) . . . . ? C28 C29 C32 C33 -2.4(7) . . . . ? C28 C29 C32 C30 179.9(5) . . . . ? C31 C30 C32 C29 -179.4(5) . . . . ? C21 C30 C32 C29 -1.1(8) . . . . ? C31 C30 C32 C33 2.7(5) . . . . ? C21 C30 C32 C33 -178.9(4) . . . . ? C27 C26 C33 C32 0.1(7) . . . . ? C35 C26 C33 C32 -179.9(4) . . . . ? C27 C26 C33 S21 -179.0(4) . . . . ? C35 C26 C33 S21 1.0(6) . . . . ? C29 C32 C33 C26 0.7(6) . . . . ? C30 C32 C33 C26 178.9(4) . . . . ? C29 C32 C33 S21 179.9(3) . . . . ? C30 C32 C33 S21 -1.9(5) . . . . ? C31 S21 C33 C26 179.7(4) . . . . ? C31 S21 C33 C32 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.236 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.061 data_compound_6 _database_code_depnum_ccdc_archive 'CCDC 253627' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4,5-dibromo-2,7-dinitrofluorenone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H4 Br2 N2 O5' _chemical_formula_weight 428.00 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.3660(2) _cell_length_b 16.0720(5) _cell_length_c 8.3120(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.3720(18) _cell_angle_gamma 90.00 _cell_volume 1347.26(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8370 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.999 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 6.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1521 _exptl_absorpt_correction_T_max 0.4642 _exptl_absorpt_process_details 'Multiscan, sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14094 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 31.00 _reflns_number_total 4181 _reflns_number_gt 2593 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement KappaCCD _computing_data_reduction 'Denzo, Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v 5.03' _computing_structure_refinement 'SHELXTL v 5.03' _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^)+(0.0526P)^2^+1.8568P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4181 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1155 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.002 _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 0.7042(6) -0.0241(3) 0.3905(6) 0.0556(13) Uani 1 1 d . . . H1 H 0.7399 -0.0747 0.3682 0.067 Uiso 1 1 calc R . . C2 C 0.5810(6) 0.0024(3) 0.3039(6) 0.0556(13) Uani 1 1 d . . . C3 C 0.5212(5) 0.0743(3) 0.3420(6) 0.0516(12) Uani 1 1 d . . . H3 H 0.4356 0.0880 0.2854 0.062 Uiso 1 1 calc R . . C4 C 0.5918(5) 0.1266(3) 0.4676(6) 0.0455(11) Uani 1 1 d . . . C4A C 0.7228(4) 0.1075(3) 0.5461(5) 0.0391(9) Uani 1 1 d . . . C4B C 0.8277(4) 0.1485(3) 0.6740(5) 0.0391(9) Uani 1 1 d . . . C5 C 0.8554(4) 0.2301(3) 0.7265(5) 0.0389(9) Uani 1 1 d . . . C6 C 0.9675(4) 0.2472(3) 0.8556(6) 0.0441(10) Uani 1 1 d . . . H6 H 0.9857 0.3014 0.8933 0.053 Uiso 1 1 calc R . . C7 C 1.0491(4) 0.1832(3) 0.9247(6) 0.0468(11) Uani 1 1 d . . . C8 C 1.0346(5) 0.1028(3) 0.8645(6) 0.0503(12) Uani 1 1 d . . . H8 H 1.0956 0.0612 0.9063 0.060 Uiso 1 1 calc R . . C8A C 0.9246(5) 0.0879(3) 0.7387(6) 0.0460(11) Uani 1 1 d . . . C9 C 0.8951(5) 0.0113(3) 0.6373(7) 0.0531(12) Uani 1 1 d . . . C9A C 0.7710(5) 0.0288(3) 0.5121(6) 0.0475(11) Uani 1 1 d . . . O1 O 0.9615(4) -0.0515(3) 0.6514(6) 0.0816(13) Uani 1 1 d . . . N1 N 0.5061(7) -0.0498(3) 0.1673(6) 0.0770(17) Uani 1 1 d . . . O2 O 0.5712(7) -0.0977(3) 0.1038(6) 0.1053(19) Uani 1 1 d . . . O3 O 0.3849(6) -0.0412(3) 0.1286(6) 0.1000(18) Uani 1 1 d . . . N4 N 1.1622(5) 0.2032(4) 1.0631(6) 0.0645(13) Uani 1 1 d . . . O4 O 1.1766(4) 0.2743(3) 1.1135(6) 0.0802(13) Uani 1 1 d . . . O5 O 1.2328(5) 0.1462(4) 1.1228(7) 0.121(2) Uani 1 1 d . . . Br1 Br 0.49007(5) 0.21076(4) 0.53475(9) 0.0647(2) Uani 1 1 d . . . Br2 Br 0.76485(5) 0.32412(3) 0.62075(6) 0.04831(16) 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 0.082(4) 0.032(2) 0.053(3) -0.003(2) 0.015(3) -0.005(2) C2 0.083(4) 0.043(3) 0.036(3) 0.001(2) 0.003(2) -0.024(3) C3 0.061(3) 0.045(3) 0.041(3) 0.011(2) -0.002(2) -0.012(2) C4 0.050(3) 0.038(2) 0.046(3) 0.007(2) 0.007(2) -0.005(2) C4A 0.047(2) 0.030(2) 0.041(2) 0.0027(18) 0.0099(19) -0.0004(17) C4B 0.043(2) 0.036(2) 0.038(2) 0.0012(18) 0.0084(18) -0.0003(18) C5 0.047(2) 0.033(2) 0.039(2) 0.0036(18) 0.0157(19) 0.0029(18) C6 0.045(2) 0.046(3) 0.042(3) -0.004(2) 0.013(2) -0.006(2) C7 0.041(2) 0.058(3) 0.040(2) -0.001(2) 0.0057(19) -0.007(2) C8 0.042(2) 0.054(3) 0.053(3) 0.010(2) 0.007(2) 0.008(2) C8A 0.048(3) 0.038(2) 0.051(3) 0.001(2) 0.009(2) 0.0005(19) C9 0.058(3) 0.039(3) 0.060(3) 0.003(2) 0.009(2) 0.009(2) C9A 0.057(3) 0.032(2) 0.053(3) -0.001(2) 0.011(2) -0.002(2) O1 0.080(3) 0.047(2) 0.108(4) -0.007(2) 0.002(2) 0.023(2) N1 0.123(5) 0.051(3) 0.047(3) 0.004(2) -0.001(3) -0.034(3) O2 0.172(6) 0.071(3) 0.073(3) -0.030(3) 0.028(3) -0.032(4) O3 0.124(5) 0.075(3) 0.079(3) -0.003(3) -0.021(3) -0.043(3) N4 0.044(2) 0.083(4) 0.063(3) -0.002(3) 0.007(2) -0.001(2) O4 0.072(3) 0.083(3) 0.075(3) -0.019(2) -0.002(2) -0.026(2) O5 0.085(3) 0.120(5) 0.122(5) -0.023(4) -0.046(3) 0.027(3) Br1 0.0459(3) 0.0472(3) 0.0967(5) -0.0002(3) 0.0079(3) 0.0057(2) Br2 0.0564(3) 0.0316(2) 0.0578(3) -0.0008(2) 0.0149(2) 0.0034(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 C1 C9A 1.378(7) . ? C1 C2 1.380(8) . ? C1 H1 0.9300 . ? C2 C3 1.383(8) . ? C2 N1 1.479(7) . ? C3 C4 1.406(7) . ? C3 H3 0.9300 . ? C4 C4A 1.397(6) . ? C4 Br1 1.878(5) . ? C4A C9A 1.413(6) . ? C4A C4B 1.488(6) . ? C4B C5 1.391(6) . ? C4B C8A 1.414(6) . ? C5 C6 1.414(6) . ? C5 Br2 1.885(4) . ? C6 C7 1.371(7) . ? C6 H6 0.9300 . ? C7 C8 1.381(7) . ? C7 N4 1.475(7) . ? C8 C8A 1.378(7) . ? C8 H8 0.9300 . ? C8A C9 1.484(7) . ? C9 O1 1.212(6) . ? C9 C9A 1.482(7) . ? N1 O2 1.220(8) . ? N1 O3 1.231(8) . ? N4 O5 1.206(7) . ? N4 O4 1.214(6) . ? 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 C9A C1 C2 116.1(5) . . ? C9A C1 H1 121.9 . . ? C2 C1 H1 121.9 . . ? C1 C2 C3 123.2(5) . . ? C1 C2 N1 118.9(5) . . ? C3 C2 N1 117.9(6) . . ? C2 C3 C4 119.1(5) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C4A C4 C3 119.9(5) . . ? C4A C4 Br1 124.8(4) . . ? C3 C4 Br1 114.8(4) . . ? C4 C4A C9A 117.0(4) . . ? C4 C4A C4B 135.0(4) . . ? C9A C4A C4B 107.8(4) . . ? C5 C4B C8A 117.0(4) . . ? C5 C4B C4A 134.9(4) . . ? C8A C4B C4A 107.7(4) . . ? C4B C5 C6 119.7(4) . . ? C4B C5 Br2 124.4(3) . . ? C6 C5 Br2 115.5(3) . . ? C7 C6 C5 119.4(4) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 123.1(4) . . ? C6 C7 N4 117.7(5) . . ? C8 C7 N4 119.1(5) . . ? C8A C8 C7 116.1(5) . . ? C8A C8 H8 122.0 . . ? C7 C8 H8 122.0 . . ? C8 C8A C4B 124.0(5) . . ? C8 C8A C9 127.0(5) . . ? C4B C8A C9 108.7(4) . . ? O1 C9 C9A 127.4(5) . . ? O1 C9 C8A 126.7(5) . . ? C9A C9 C8A 105.9(4) . . ? C1 C9A C4A 123.9(5) . . ? C1 C9A C9 127.2(5) . . ? C4A C9A C9 108.6(4) . . ? O2 N1 O3 126.2(6) . . ? O2 N1 C2 116.4(6) . . ? O3 N1 C2 117.4(6) . . ? O5 N4 O4 124.0(6) . . ? O5 N4 C7 116.9(6) . . ? O4 N4 C7 119.1(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 -4.8(8) . . . . ? C9A C1 C2 N1 177.6(4) . . . . ? C1 C2 C3 C4 4.5(8) . . . . ? N1 C2 C3 C4 -177.9(4) . . . . ? C2 C3 C4 C4A 3.2(7) . . . . ? C2 C3 C4 Br1 -169.0(4) . . . . ? C3 C4 C4A C9A -9.7(7) . . . . ? Br1 C4 C4A C9A 161.7(3) . . . . ? C3 C4 C4A C4B 176.5(5) . . . . ? Br1 C4 C4A C4B -12.1(8) . . . . ? C4 C4A C4B C5 -25.6(9) . . . . ? C9A C4A C4B C5 160.1(5) . . . . ? C4 C4A C4B C8A 162.3(5) . . . . ? C9A C4A C4B C8A -11.9(5) . . . . ? C8A C4B C5 C6 -8.4(6) . . . . ? C4A C4B C5 C6 -179.8(5) . . . . ? C8A C4B C5 Br2 164.0(4) . . . . ? C4A C4B C5 Br2 -7.5(7) . . . . ? C4B C5 C6 C7 1.5(6) . . . . ? Br2 C5 C6 C7 -171.5(3) . . . . ? C5 C6 C7 C8 6.2(7) . . . . ? C5 C6 C7 N4 -177.9(4) . . . . ? C6 C7 C8 C8A -6.0(7) . . . . ? N4 C7 C8 C8A 178.1(4) . . . . ? C7 C8 C8A C4B -1.6(7) . . . . ? C7 C8 C8A C9 171.0(5) . . . . ? C5 C4B C8A C8 8.7(7) . . . . ? C4A C4B C8A C8 -177.6(4) . . . . ? C5 C4B C8A C9 -165.1(4) . . . . ? C4A C4B C8A C9 8.6(5) . . . . ? C8 C8A C9 O1 2.0(9) . . . . ? C4B C8A C9 O1 175.6(6) . . . . ? C8 C8A C9 C9A -175.9(5) . . . . ? C4B C8A C9 C9A -2.3(6) . . . . ? C2 C1 C9A C4A -2.5(8) . . . . ? C2 C1 C9A C9 171.1(5) . . . . ? C4 C4A C9A C1 9.6(7) . . . . ? C4B C4A C9A C1 -175.0(5) . . . . ? C4 C4A C9A C9 -165.0(4) . . . . ? C4B C4A C9A C9 10.4(5) . . . . ? O1 C9 C9A C1 2.5(9) . . . . ? C8A C9 C9A C1 -179.6(5) . . . . ? O1 C9 C9A C4A 176.9(6) . . . . ? C8A C9 C9A C4A -5.2(5) . . . . ? C1 C2 N1 O2 -23.1(7) . . . . ? C3 C2 N1 O2 159.1(5) . . . . ? C1 C2 N1 O3 156.7(5) . . . . ? C3 C2 N1 O3 -21.0(7) . . . . ? C6 C7 N4 O5 179.8(6) . . . . ? C8 C7 N4 O5 -4.1(8) . . . . ? C6 C7 N4 O4 2.1(7) . . . . ? C8 C7 N4 O4 178.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.977 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.121