# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Prof Akira Mori' _publ_contact_author_address ; Institute of Advanced Material Study Kyushu University Kasuga-koen Kasuga Fukuoda 816-8580 JAPAN ; _publ_contact_author_email mori-a@cm.kyushu-u.ac.jp _publ_contact_author_fax +81(92)583-7806 _publ_contact_author_phone +81(92)583-7806 _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_contact_letter ; Article Ref, B300922J ; _publ_section_title ; Photochemical reactions of 2-bromotropone and 2,7-dibromotropone with 9,10-dicyanoanthracene ; loop_ _publ_author_name _publ_author_address 'Mori, Akira' ; Institute of Advanced Material Study Kyushu University Kasuga-koen, Kasuga Fukuoka 816-8580 Japan ; 'Kawakami, Hiroko' ; Graduate School of Engineering Sciences Kyushu University Kasuga-koen, Kasuga Fukuoka 816-8580 Japan ; 'Kato, Nobuo' ; Institute of Advanced Material Study Kyushu University Kasuga-koen, Kasuga Fukuoka 816-8580 Japan ; 'Wu, Shu-Ping' ; Institute of Advanced Material Study Kyushu University Kasuga-koen, Kasuga Fukuoka 816-8580 Japan ; 'Takeshita, Hitoshi' ; Institute of Advanced Material Study Kyushu University Kasuga-koen, Kasuga Fukuoka 816-8580 Japan ; # TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; All H atoms were located at ideal positions and were included in refinement, but restrained to ride on the atom to which they are bonded. Isotropic thermal factors of H atoms were held fixed to 1.2 times U~eq~ of the riding atoms. ; _publ_section_acknowledgements ;? ; data_16 _database_code_CSD 203118 _audit_creation_method SHELXL _chemical_name_systematic ; 9,10-Dicyano-9-(6-bromo-5-oxocyclohepta-1,3,6- trienyl)-10-(7-oxocyclohepta- 1,3,5-trienyl)-9,10- dihydroanthracene ; _chemical_name_common ? _chemical_formula_moiety ; C30 H17 Br N2 O2, C6 H6 ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H23 Br N2 O2' _chemical_formula_weight 595.47 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.6763 1.2805 '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 1 21/c 1' 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 10.889(2) _cell_length_b 28.960(5) _cell_length_c 9.213(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.59(2) _cell_angle_gamma 90.00 _cell_volume 2784.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.27 _cell_measurement_theta_max 45.85 _exptl_crystal_description prism _exptl_crystal_colour 'brownish yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method ? _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 2.299 _exptl_absorpt_correction_type ; empirical via \y scans (North, Phillips, & Mathews, 1968) ; _exptl_absorpt_correction_T_min 0.8236 _exptl_absorpt_correction_T_max 0.9983 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.0 _diffrn_reflns_number 5397 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 67.95 _reflns_number_total 5067 _reflns_number_observed 3815 _reflns_observed_criterion >2\s(I) _computing_data_collection ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_cell_refinement ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0693P)^2^+2.0895P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5067 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_obs 0.0480 _refine_ls_wR_factor_all 0.1446 _refine_ls_wR_factor_obs 0.1275 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.068 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max .487 _refine_diff_density_min -.725 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br Br 0.46146(4) 0.756096(14) 0.68047(7) 0.0854(2) Uani 1 d . . O1 O 0.2651(3) 0.70728(11) 0.7768(5) 0.1063(12) Uani 1 d . . C1 C 0.3354(3) 0.67774(12) 0.7482(4) 0.0570(8) Uani 1 d . . C2 C 0.4444(3) 0.69150(11) 0.6946(4) 0.0495(7) Uani 1 d . . C3 C 0.5322(3) 0.66575(10) 0.6531(3) 0.0448(7) Uani 1 d . . H3 H 0.5928(3) 0.68286(10) 0.6227(3) 0.054 Uiso 1 calc R . C4 C 0.5483(3) 0.61702(10) 0.6477(3) 0.0399(6) Uani 1 d . . C5 C 0.4734(3) 0.58438(11) 0.6842(3) 0.0484(7) Uani 1 d . . H5 H 0.4951(3) 0.55387(11) 0.6719(3) 0.058 Uiso 1 calc R . C6 C 0.3648(3) 0.59125(13) 0.7394(4) 0.0598(9) Uani 1 d . . H6 H 0.3267(3) 0.56416(13) 0.7592(4) 0.072 Uiso 1 calc R . C7 C 0.3088(3) 0.62983(13) 0.7674(4) 0.0571(8) Uani 1 d . . H7 H 0.2400(3) 0.62487(13) 0.8064(4) 0.068 Uiso 1 calc R . O1' O 0.9305(2) 0.58315(7) 0.4950(3) 0.0532(5) Uani 1 d . . C1' C 0.9980(3) 0.61081(11) 0.4518(3) 0.0451(7) Uani 1 d . . C2' C 0.9686(3) 0.66042(11) 0.4512(3) 0.0437(7) Uani 1 d . . C3' C 1.0344(3) 0.69559(13) 0.4133(4) 0.0618(9) Uani 1 d . . H3' H 1.0011(3) 0.72471(13) 0.4217(4) 0.074 Uiso 1 calc R . C4' C 1.1478(4) 0.6957(2) 0.3619(5) 0.0767(11) Uani 1 d . . H4' H 1.1772(4) 0.7248(2) 0.3446(5) 0.092 Uiso 1 calc R . C5' C 1.2163(3) 0.6603(2) 0.3356(4) 0.0763(12) Uani 1 d . . H5' H 1.2868(3) 0.6676(2) 0.3021(4) 0.092 Uiso 1 calc R . C6' C 1.1944(3) 0.6135(2) 0.3528(4) 0.0723(11) Uani 1 d . . H6' H 1.2513(3) 0.5937(2) 0.3256(4) 0.087 Uiso 1 calc R . C7' C 1.1044(3) 0.59246(14) 0.4023(4) 0.0637(9) Uani 1 d . . H7' H 1.1108(3) 0.56043(14) 0.4057(4) 0.076 Uiso 1 calc R . N1" N 0.6921(3) 0.51342(10) 0.5877(4) 0.0678(8) Uani 1 d . . N2" N 0.7945(4) 0.75778(11) 0.5058(5) 0.0861(11) Uani 1 d . . C1" C 0.9743(3) 0.67083(12) 0.7764(4) 0.0524(8) Uani 1 d . . H1" H 1.0301(3) 0.69098(12) 0.7484(4) 0.063 Uiso 1 calc R . C2" C 0.9973(3) 0.65841(14) 0.9256(4) 0.0627(9) Uani 1 d . . H2" H 1.0685(3) 0.67013(14) 0.9979(4) 0.075 Uiso 1 calc R . C3" C 0.9154(3) 0.62864(14) 0.9689(4) 0.0605(9) Uani 1 d . . H3" H 0.9307(3) 0.62036(14) 1.0700(4) 0.073 Uiso 1 calc R . C4" C 0.8103(3) 0.61123(12) 0.8604(3) 0.0507(7) Uani 1 d . . H4" H 0.7551(3) 0.59101(12) 0.8891(3) 0.061 Uiso 1 calc R . C4a" C 0.7860(3) 0.62358(10) 0.7087(3) 0.0404(6) Uani 1 d . . C5" C 0.6668(3) 0.60344(9) 0.5953(3) 0.0387(6) Uani 1 d . . C5a" C 0.6457(2) 0.61945(9) 0.4300(3) 0.0385(6) Uani 1 d . . C6" C 0.5388(3) 0.60284(11) 0.3216(3) 0.0480(7) Uani 1 d . . H6" H 0.4822(3) 0.58330(11) 0.3505(3) 0.058 Uiso 1 calc R . C7" C 0.5151(3) 0.61497(12) 0.1708(4) 0.0556(8) Uani 1 d . . H7" H 0.4427(3) 0.60387(12) 0.0990(4) 0.067 Uiso 1 calc R . C8" C 0.5994(3) 0.64355(12) 0.1279(4) 0.0551(8) Uani 1 d . . H8" H 0.5845(3) 0.65165(12) 0.0266(4) 0.066 Uiso 1 calc R . C9" C 0.7067(3) 0.66029(10) 0.2358(3) 0.0485(7) Uani 1 d . . H9" H 0.7637(3) 0.67950(10) 0.2063(3) 0.058 Uiso 1 calc R . C9a" C 0.7298(3) 0.64864(9) 0.3877(3) 0.0383(6) Uani 1 d . . C10" C 0.8477(3) 0.66985(9) 0.5023(3) 0.0407(6) Uani 1 d . . C10a" C 0.8682(3) 0.65356(10) 0.6662(3) 0.0414(6) Uani 1 d . . C11" C 0.6819(3) 0.55250(11) 0.5933(3) 0.0470(7) Uani 1 d . . C12" C 0.8203(3) 0.72009(11) 0.5028(4) 0.0548(8) Uani 1 d . . C1B C 0.7624(4) 0.52254(13) 0.1970(5) 0.0744(11) Uani 1 d . . H1B H 0.7395(4) 0.54361(13) 0.2610(5) 0.089 Uiso 1 calc R . C2B C 0.6839(5) 0.51602(14) 0.0544(6) 0.0805(12) Uani 1 d . . H2B H 0.6069(5) 0.53203(14) 0.0219(6) 0.097 Uiso 1 calc R . C3B C 0.7186(6) 0.4859(2) -0.0409(5) 0.093(2) Uani 1 d . . H3B H 0.6660(6) 0.4813(2) -0.1388(5) 0.111 Uiso 1 calc R . C4B C 0.8331(6) 0.4624(2) 0.0105(6) 0.103(2) Uani 1 d . . H4B H 0.8587(6) 0.4423(2) -0.0539(6) 0.123 Uiso 1 calc R . C5B C 0.9084(5) 0.4685(2) 0.1544(6) 0.0926(14) Uani 1 d . . H5B H 0.9842(5) 0.4519(2) 0.1894(6) 0.111 Uiso 1 calc R . C6B C 0.8731(4) 0.49877(14) 0.2467(5) 0.0759(11) Uani 1 d . . H6B H 0.9253(4) 0.50322(14) 0.3449(5) 0.091 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.0797(3) 0.0486(2) 0.1426(5) -0.0084(2) 0.0555(3) 0.0026(2) O1 0.073(2) 0.087(2) 0.187(3) -0.049(2) 0.083(2) -0.011(2) C1 0.038(2) 0.070(2) 0.068(2) -0.021(2) 0.0232(15) -0.0060(15) C2 0.0400(15) 0.050(2) 0.061(2) -0.0055(14) 0.0179(14) -0.0007(13) C3 0.0358(14) 0.049(2) 0.055(2) 0.0004(13) 0.0222(13) -0.0032(12) C4 0.0360(14) 0.045(2) 0.0422(15) 0.0008(12) 0.0173(12) -0.0026(11) C5 0.045(2) 0.049(2) 0.057(2) 0.0044(14) 0.0232(14) -0.0037(13) C6 0.050(2) 0.065(2) 0.073(2) 0.013(2) 0.032(2) -0.011(2) C7 0.040(2) 0.080(2) 0.059(2) 0.001(2) 0.0272(15) -0.004(2) O1' 0.0543(12) 0.0474(12) 0.0651(14) -0.0024(10) 0.0288(11) 0.0024(10) C1' 0.0362(14) 0.059(2) 0.041(2) -0.0079(13) 0.0124(12) 0.0010(13) C2' 0.0362(14) 0.056(2) 0.043(2) -0.0015(13) 0.0177(12) -0.0044(12) C3' 0.056(2) 0.063(2) 0.074(2) 0.005(2) 0.031(2) -0.012(2) C4' 0.064(2) 0.094(3) 0.081(3) 0.015(2) 0.036(2) -0.022(2) C5' 0.043(2) 0.134(4) 0.061(2) 0.003(2) 0.029(2) -0.008(2) C6' 0.041(2) 0.118(4) 0.063(2) -0.020(2) 0.023(2) 0.002(2) C7' 0.043(2) 0.084(3) 0.068(2) -0.019(2) 0.021(2) 0.004(2) N1" 0.088(2) 0.045(2) 0.078(2) 0.0018(14) 0.035(2) 0.0059(15) N2" 0.109(3) 0.045(2) 0.121(3) -0.008(2) 0.060(2) 0.002(2) C1" 0.043(2) 0.063(2) 0.056(2) -0.016(2) 0.0213(14) -0.0052(14) C2" 0.043(2) 0.086(3) 0.055(2) -0.022(2) 0.008(2) 0.004(2) C3" 0.053(2) 0.088(3) 0.041(2) -0.004(2) 0.0150(15) 0.014(2) C4" 0.047(2) 0.065(2) 0.046(2) 0.0045(15) 0.0232(14) 0.0067(14) C4a" 0.0349(14) 0.049(2) 0.041(2) -0.0030(12) 0.0157(12) 0.0033(12) C5" 0.0367(14) 0.0388(14) 0.045(2) 0.0011(12) 0.0187(12) -0.0007(11) C5a" 0.0345(13) 0.0429(14) 0.0415(15) -0.0017(12) 0.0163(11) 0.0025(11) C6" 0.0390(15) 0.058(2) 0.050(2) -0.0044(14) 0.0161(13) -0.0017(13) C7" 0.044(2) 0.069(2) 0.050(2) -0.006(2) 0.0075(14) 0.007(2) C8" 0.057(2) 0.067(2) 0.041(2) 0.0092(15) 0.0142(15) 0.014(2) C9" 0.052(2) 0.049(2) 0.051(2) 0.0090(14) 0.0244(15) 0.0077(13) C9a" 0.0383(14) 0.0378(14) 0.043(2) 0.0009(11) 0.0192(12) 0.0061(11) C10" 0.0390(14) 0.0381(14) 0.051(2) -0.0032(12) 0.0218(13) -0.0037(11) C10a" 0.0364(14) 0.0464(15) 0.046(2) -0.0075(12) 0.0187(12) 0.0004(12) C11" 0.050(2) 0.048(2) 0.047(2) 0.0012(13) 0.0213(14) 0.0008(13) C12" 0.060(2) 0.044(2) 0.069(2) -0.0051(15) 0.033(2) -0.0055(14) C1B 0.092(3) 0.057(2) 0.081(3) -0.010(2) 0.037(2) -0.002(2) C2B 0.084(3) 0.058(2) 0.096(3) 0.014(2) 0.020(3) 0.004(2) C3B 0.138(5) 0.071(3) 0.059(2) 0.009(2) 0.013(3) -0.020(3) C4B 0.142(5) 0.096(4) 0.088(4) -0.016(3) 0.062(4) 0.010(3) C5B 0.077(3) 0.092(3) 0.116(4) -0.015(3) 0.038(3) 0.007(2) C6B 0.075(3) 0.067(2) 0.082(3) -0.012(2) 0.016(2) -0.009(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 Br C2 1.888(3) . ? O1 C1 1.226(4) . ? C1 C7 1.438(5) . ? C1 C2 1.465(4) . ? C2 C3 1.351(4) . ? C3 C4 1.425(4) . ? C4 C5 1.353(4) . ? C4 C5" 1.552(4) . ? C5 C6 1.428(4) . ? C6 C7 1.333(5) . ? O1' C1' 1.228(4) . ? C1' C7' 1.461(4) . ? C1' C2' 1.471(4) . ? C2' C3' 1.347(4) . ? C2' C10" 1.544(4) . ? C3' C4' 1.444(5) . ? C4' C5' 1.331(6) . ? C5' C6' 1.393(6) . ? C6' C7' 1.340(5) . ? N1" C11" 1.140(4) . ? N2" C12" 1.130(4) . ? C1" C2" 1.374(5) . ? C1" C10a" 1.395(4) . ? C2" C3" 1.379(5) . ? C3" C4" 1.382(5) . ? C4" C4a" 1.393(4) . ? C4a" C10a" 1.381(4) . ? C4a" C5" 1.530(4) . ? C5" C11" 1.485(4) . ? C5" C5a" 1.545(4) . ? C5a" C9a" 1.382(4) . ? C5a" C6" 1.386(4) . ? C6" C7" 1.384(4) . ? C7" C8" 1.375(5) . ? C8" C9" 1.388(5) . ? C9" C9a" 1.391(4) . ? C9a" C10" 1.538(4) . ? C10" C12" 1.485(4) . ? C10" C10a" 1.536(4) . ? C1B C6B 1.349(6) . ? C1B C2B 1.361(6) . ? C2B C3B 1.364(7) . ? C3B C4B 1.380(7) . ? C4B C5B 1.357(7) . ? C5B C6B 1.351(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 O1 C1 C7 119.1(3) . . ? O1 C1 C2 119.9(3) . . ? C7 C1 C2 121.0(3) . . ? C3 C2 C1 130.7(3) . . ? C3 C2 Br 115.8(2) . . ? C1 C2 Br 113.5(2) . . ? C2 C3 C4 131.4(3) . . ? C5 C4 C3 126.5(3) . . ? C5 C4 C5" 121.0(3) . . ? C3 C4 C5" 112.6(2) . . ? C4 C5 C6 127.7(3) . . ? C7 C6 C5 131.0(3) . . ? C6 C7 C1 131.7(3) . . ? O1' C1' C7' 117.7(3) . . ? O1' C1' C2' 119.3(2) . . ? C7' C1' C2' 123.0(3) . . ? C3' C2' C1' 127.4(3) . . ? C3' C2' C10" 120.5(3) . . ? C1' C2' C10" 112.0(2) . . ? C2' C3' C4' 130.9(4) . . ? C5' C4' C3' 129.4(4) . . ? C4' C5' C6' 127.3(3) . . ? C7' C6' C5' 130.3(4) . . ? C6' C7' C1' 131.5(4) . . ? C2" C1" C10a" 120.7(3) . . ? C1" C2" C3" 120.3(3) . . ? C2" C3" C4" 119.3(3) . . ? C3" C4" C4a" 120.8(3) . . ? C10a" C4a" C4" 119.6(3) . . ? C10a" C4a" C5" 122.5(2) . . ? C4" C4a" C5" 117.9(3) . . ? C11" C5" C4a" 108.2(2) . . ? C11" C5" C5a" 105.8(2) . . ? C4a" C5" C5a" 114.7(2) . . ? C11" C5" C4 111.1(2) . . ? C4a" C5" C4 108.0(2) . . ? C5a" C5" C4 109.1(2) . . ? C9a" C5a" C6" 119.8(3) . . ? C9a" C5a" C5" 122.5(2) . . ? C6" C5a" C5" 117.7(2) . . ? C7" C6" C5a" 120.8(3) . . ? C8" C7" C6" 119.6(3) . . ? C7" C8" C9" 119.9(3) . . ? C8" C9" C9a" 120.7(3) . . ? C5a" C9a" C9" 119.2(3) . . ? C5a" C9a" C10" 122.8(2) . . ? C9" C9a" C10" 118.0(2) . . ? C12" C10" C10a" 105.7(2) . . ? C12" C10" C9a" 105.3(2) . . ? C10a" C10" C9a" 114.2(2) . . ? C12" C10" C2' 111.3(2) . . ? C10a" C10" C2' 110.4(2) . . ? C9a" C10" C2' 109.7(2) . . ? C4a" C10a" C1" 119.2(3) . . ? C4a" C10a" C10" 123.2(2) . . ? C1" C10a" C10" 117.6(3) . . ? N1" C11" C5" 178.2(3) . . ? N2" C12" C10" 176.6(4) . . ? C6B C1B C2B 120.7(4) . . ? C1B C2B C3B 119.8(4) . . ? C2B C3B C4B 119.0(4) . . ? C5B C4B C3B 120.3(4) . . ? C6B C5B C4B 119.9(5) . . ? C1B C6B C5B 120.3(4) . . ? 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 O1 C1 C2 C3 -178.3(4) . . . . ? C7 C1 C2 C3 1.4(6) . . . . ? O1 C1 C2 Br 1.0(5) . . . . ? C7 C1 C2 Br -179.3(3) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? Br C2 C3 C4 -179.4(3) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C2 C3 C4 C5" -178.6(3) . . . . ? C3 C4 C5 C6 -1.8(5) . . . . ? C5" C4 C5 C6 177.4(3) . . . . ? C4 C5 C6 C7 0.9(6) . . . . ? C5 C6 C7 C1 1.9(7) . . . . ? O1 C1 C7 C6 176.8(4) . . . . ? C2 C1 C7 C6 -2.9(6) . . . . ? O1' C1' C2' C3' 177.3(3) . . . . ? C7' C1' C2' C3' -3.0(5) . . . . ? O1' C1' C2' C10" -2.3(4) . . . . ? C7' C1' C2' C10" 177.4(3) . . . . ? C1' C2' C3' C4' 0.9(6) . . . . ? C10" C2' C3' C4' -179.5(4) . . . . ? C2' C3' C4' C5' 1.4(7) . . . . ? C3' C4' C5' C6' -0.3(8) . . . . ? C4' C5' C6' C7' -2.0(7) . . . . ? C5' C6' C7' C1' 1.4(7) . . . . ? O1' C1' C7' C6' -178.5(4) . . . . ? C2' C1' C7' C6' 1.7(6) . . . . ? C10a" C1" C2" C3" -0.1(5) . . . . ? C1" C2" C3" C4" 0.4(5) . . . . ? C2" C3" C4" C4a" -0.3(5) . . . . ? C3" C4" C4a" C10a" 0.1(4) . . . . ? C3" C4" C4a" C5" -179.2(3) . . . . ? C10a" C4a" C5" C11" 117.6(3) . . . . ? C4" C4a" C5" C11" -63.2(3) . . . . ? C10a" C4a" C5" C5a" -0.2(4) . . . . ? C4" C4a" C5" C5a" 179.1(2) . . . . ? C10a" C4a" C5" C4 -122.1(3) . . . . ? C4" C4a" C5" C4 57.2(3) . . . . ? C5 C4 C5" C11" -0.2(4) . . . . ? C3 C4 C5" C11" 179.1(3) . . . . ? C5 C4 C5" C4a" -118.7(3) . . . . ? C3 C4 C5" C4a" 60.6(3) . . . . ? C5 C4 C5" C5a" 116.0(3) . . . . ? C3 C4 C5" C5a" -64.7(3) . . . . ? C11" C5" C5a" C9a" -117.4(3) . . . . ? C4a" C5" C5a" C9a" 1.7(4) . . . . ? C4 C5" C5a" C9a" 123.0(3) . . . . ? C11" C5" C5a" C6" 61.5(3) . . . . ? C4a" C5" C5a" C6" -179.4(2) . . . . ? C4 C5" C5a" C6" -58.1(3) . . . . ? C9a" C5a" C6" C7" 0.3(4) . . . . ? C5" C5a" C6" C7" -178.7(3) . . . . ? C5a" C6" C7" C8" 0.6(5) . . . . ? C6" C7" C8" C9" -0.5(5) . . . . ? C7" C8" C9" C9a" -0.3(5) . . . . ? C6" C5a" C9a" C9" -1.1(4) . . . . ? C5" C5a" C9a" C9" 177.8(2) . . . . ? C6" C5a" C9a" C10" 177.7(2) . . . . ? C5" C5a" C9a" C10" -3.4(4) . . . . ? C8" C9" C9a" C5a" 1.1(4) . . . . ? C8" C9" C9a" C10" -177.7(3) . . . . ? C5a" C9a" C10" C12" -112.1(3) . . . . ? C9" C9a" C10" C12" 66.6(3) . . . . ? C5a" C9a" C10" C10a" 3.4(4) . . . . ? C9" C9a" C10" C10a" -177.8(2) . . . . ? C5a" C9a" C10" C2' 128.0(3) . . . . ? C9" C9a" C10" C2' -53.3(3) . . . . ? C3' C2' C10" C12" -0.3(4) . . . . ? C1' C2' C10" C12" 179.3(3) . . . . ? C3' C2' C10" C10a" -117.4(3) . . . . ? C1' C2' C10" C10a" 62.3(3) . . . . ? C3' C2' C10" C9a" 115.9(3) . . . . ? C1' C2' C10" C9a" -64.5(3) . . . . ? C4" C4a" C10a" C1" 0.2(4) . . . . ? C5" C4a" C10a" C1" 179.4(3) . . . . ? C4" C4a" C10a" C10" -178.8(3) . . . . ? C5" C4a" C10a" C10" 0.5(4) . . . . ? C2" C1" C10a" C4a" -0.2(4) . . . . ? C2" C1" C10a" C10" 178.8(3) . . . . ? C12" C10" C10a" C4a" 113.4(3) . . . . ? C9a" C10" C10a" C4a" -1.9(4) . . . . ? C2' C10" C10a" C4a" -126.1(3) . . . . ? C12" C10" C10a" C1" -65.6(3) . . . . ? C9a" C10" C10a" C1" 179.1(2) . . . . ? C2' C10" C10a" C1" 54.9(3) . . . . ? C6B C1B C2B C3B -1.5(7) . . . . ? C1B C2B C3B C4B 0.4(7) . . . . ? C2B C3B C4B C5B 1.3(8) . . . . ? C3B C4B C5B C6B -1.9(8) . . . . ? C2B C1B C6B C5B 0.9(7) . . . . ? C4B C5B C6B C1B 0.8(8) . . . . ? data_17 _database_code_CSD 203119 _audit_creation_method SHELXL _chemical_name_systematic ; 2-Bromo-7-(10-cyano-9-anthryl) cyclohepta-2,4,6-trien-1-one ; _chemical_name_common ; 2-Bromo-7-(10-cyano-9-anthryl)tropone ; _chemical_formula_moiety 'C22 H12 Br1 N1 O1' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H12 Br1 N1 O1' _chemical_formula_weight 386.25 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.772(3) _cell_length_b 7.698(1) _cell_length_c 25.944(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.46(2) _cell_angle_gamma 90.00 _cell_volume 3339.5(11) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 21 _cell_measurement_theta_max 43 _exptl_crystal_description prism _exptl_crystal_colour 'brownish yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method ? _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 3.417 _exptl_absorpt_correction_type ; empirical via \y scans (North, A. T. C., Phillips, D. C. & Mathews, F. S., 1968) ; _exptl_absorpt_correction_T_min 0.859 _exptl_absorpt_correction_T_max 0.995 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3250 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 69.94 _reflns_number_total 3171 _reflns_number_observed 2577 _reflns_observed_criterion >2\s(I) _computing_data_collection 'CAD4 Enraf-Nonius software' _computing_cell_refinement 'CAD4 Enraf-Nonius software' _computing_data_reduction 'MolEN Enraf-Nonius software' _computing_structure_solution ;SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+( 0.0533P)^2^+4.6810P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00092(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3171 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_obs 0.0428 _refine_ls_wR_factor_all 0.1214 _refine_ls_wR_factor_obs 0.1110 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.083 _refine_ls_restrained_S_all 1.059 _refine_ls_restrained_S_obs 1.083 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max .526 _refine_diff_density_min -.532 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.58382(3) 0.89815(6) 0.202118(15) 0.0937(2) Uani 1 d . . O1 O 0.6838(2) 0.7755(3) 0.29027(10) 0.0904(8) Uani 1 d . . N1 N 0.8800(2) 0.3451(4) 0.4901(2) 0.0999(11) Uani 1 d . . C1 C 0.6766(2) 0.9324(4) 0.29630(11) 0.0569(7) Uani 1 d . . C2 C 0.6312(2) 1.0347(4) 0.25712(11) 0.0589(7) Uani 1 d . . C3 C 0.6194(2) 1.2081(4) 0.25261(13) 0.0718(9) Uani 1 d . . H3 H 0.5870(2) 1.2422(4) 0.22366(13) 0.086 Uiso 1 calc R . C4 C 0.6484(2) 1.3452(4) 0.28468(14) 0.0717(9) Uani 1 d . . H4 H 0.6349(2) 1.4565(4) 0.27311(14) 0.086 Uiso 1 calc R . C5 C 0.6926(2) 1.3359(4) 0.32949(14) 0.0700(9) Uani 1 d . . H5 H 0.7075(2) 1.4413(4) 0.34486(14) 0.084 Uiso 1 calc R . C6 C 0.7200(2) 1.1832(4) 0.35677(12) 0.0617(7) Uani 1 d . . H6 H 0.7467(2) 1.2042(4) 0.38892(12) 0.074 Uiso 1 calc R . C7 C 0.7135(2) 1.0125(3) 0.34372(10) 0.0512(6) Uani 1 d . . C1' C 0.8866(2) 0.9616(4) 0.35607(11) 0.0599(7) Uani 1 d . . H1' H 0.8653(2) 1.0512(4) 0.33528(11) 0.072 Uiso 1 calc R . C2' C 0.9668(2) 0.9338(5) 0.36013(13) 0.0702(9) Uani 1 d . . H2' H 0.9999(2) 1.0049(5) 0.34216(13) 0.084 Uiso 1 calc R . C3' C 1.0002(2) 0.7990(5) 0.39117(14) 0.0715(9) Uani 1 d . . H3' H 1.0553(2) 0.7826(5) 0.39389(14) 0.086 Uiso 1 calc R . C4' C 0.9534(2) 0.6932(4) 0.41704(12) 0.0632(7) Uani 1 d . . H4' H 0.9765(2) 0.6036(4) 0.43708(12) 0.076 Uiso 1 calc R . C4'a C 0.8692(2) 0.7169(4) 0.41409(10) 0.0523(6) Uani 1 d . . C5' C 0.6859(2) 0.5369(4) 0.46993(11) 0.0582(7) Uani 1 d . . H5' H 0.7075(2) 0.4443(4) 0.48936(11) 0.070 Uiso 1 calc R . C6' C 0.6072(2) 0.5716(4) 0.46962(13) 0.0650(8) Uani 1 d . . H6' H 0.5750(2) 0.5034(4) 0.48911(13) 0.078 Uiso 1 calc R . C7' C 0.5731(2) 0.7100(4) 0.44011(14) 0.0670(8) Uani 1 d . . H7' H 0.5188(2) 0.7331(4) 0.44064(14) 0.080 Uiso 1 calc R . C8' C 0.6186(2) 0.8100(4) 0.41093(12) 0.0595(7) Uani 1 d . . H8' H 0.5949(2) 0.8995(4) 0.39115(12) 0.071 Uiso 1 calc R . C8'a C 0.7024(2) 0.7794(3) 0.41019(10) 0.0492(6) Uani 1 d . . C9' C 0.7511(2) 0.8813(3) 0.38051(10) 0.0501(6) Uani 1 d . . C9'a C 0.8347(2) 0.8547(3) 0.38333(10) 0.0498(6) Uani 1 d . . C10' C 0.8188(2) 0.6095(3) 0.44077(11) 0.0531(6) Uani 1 d . . C10'a C 0.7364(2) 0.6404(3) 0.44082(10) 0.0494(6) Uani 1 d . . C11' C 0.8530(2) 0.4630(4) 0.46892(13) 0.0670(8) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1225(4) 0.0810(3) 0.0713(3) -0.0138(2) -0.0320(2) 0.0191(2) O1 0.141(2) 0.0435(12) 0.080(2) -0.0106(11) -0.0379(15) 0.0173(13) N1 0.084(2) 0.073(2) 0.139(3) 0.036(2) -0.018(2) 0.005(2) C1 0.070(2) 0.0416(14) 0.058(2) -0.0010(12) -0.0018(13) 0.0055(13) C2 0.072(2) 0.052(2) 0.053(2) -0.0010(13) 0.0009(13) 0.0071(14) C3 0.093(2) 0.057(2) 0.066(2) 0.0130(15) 0.004(2) 0.014(2) C4 0.095(2) 0.0415(15) 0.080(2) 0.0100(15) 0.014(2) 0.011(2) C5 0.092(2) 0.0374(14) 0.082(2) -0.0035(15) 0.015(2) -0.0001(15) C6 0.077(2) 0.0450(15) 0.062(2) -0.0066(13) 0.0026(14) 0.0006(14) C7 0.0574(15) 0.0433(13) 0.0525(14) -0.0002(11) 0.0023(12) 0.0015(12) C1' 0.063(2) 0.058(2) 0.058(2) -0.0048(14) 0.0031(13) -0.0069(14) C2' 0.065(2) 0.072(2) 0.074(2) -0.010(2) 0.011(2) -0.018(2) C3' 0.053(2) 0.078(2) 0.082(2) -0.015(2) -0.002(2) -0.004(2) C4' 0.057(2) 0.061(2) 0.069(2) -0.0102(15) -0.0090(14) 0.0041(14) C4'a 0.0542(14) 0.0500(14) 0.0510(14) -0.0097(12) -0.0061(11) 0.0003(12) C5' 0.071(2) 0.0488(15) 0.054(2) 0.0005(12) -0.0001(13) -0.0050(14) C6' 0.073(2) 0.058(2) 0.065(2) -0.0035(14) 0.0122(15) -0.0121(15) C7' 0.056(2) 0.060(2) 0.085(2) -0.008(2) 0.0100(15) -0.0025(14) C8' 0.059(2) 0.0497(15) 0.069(2) -0.0025(14) 0.0021(13) 0.0045(13) C8'a 0.0537(14) 0.0420(13) 0.0511(14) -0.0063(11) -0.0016(11) 0.0001(11) C9' 0.0585(15) 0.0415(13) 0.0490(14) -0.0044(11) -0.0028(11) 0.0014(11) C9'a 0.0561(14) 0.0461(13) 0.0463(13) -0.0074(11) -0.0014(11) -0.0027(11) C10' 0.061(2) 0.0450(14) 0.0512(14) -0.0035(11) -0.0089(12) 0.0009(12) C10'a 0.0589(15) 0.0426(13) 0.0456(13) -0.0061(11) -0.0030(11) -0.0019(11) C11' 0.065(2) 0.057(2) 0.077(2) 0.006(2) -0.012(2) -0.0011(15) _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 Br1 C2 1.896(3) . ? O1 C1 1.225(3) . ? N1 C11' 1.137(4) . ? C1 C2 1.454(4) . ? C1 C7 1.469(4) . ? C2 C3 1.353(4) . ? C3 C4 1.407(5) . ? C4 C5 1.332(5) . ? C5 C6 1.429(4) . ? C6 C7 1.359(4) . ? C7 C9' 1.495(4) . ? C1' C2' 1.359(4) . ? C1' C9'a 1.425(4) . ? C2' C3' 1.403(5) . ? C3' C4' 1.346(5) . ? C4' C4'a 1.421(4) . ? C4'a C10' 1.402(4) . ? C4'a C9'a 1.423(4) . ? C5' C6' 1.347(4) . ? C5' C10'a 1.421(4) . ? C6' C7' 1.407(5) . ? C7' C8' 1.355(4) . ? C8' C8'a 1.426(4) . ? C8'a C9' 1.405(4) . ? C8'a C10'a 1.425(4) . ? C9' C9'a 1.412(4) . ? C10' C10'a 1.403(4) . ? C10' C11' 1.439(4) . ? 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 O1 C1 C2 119.8(3) . . ? O1 C1 C7 118.8(3) . . ? C2 C1 C7 121.4(2) . . ? C3 C2 C1 131.3(3) . . ? C3 C2 Br1 115.6(2) . . ? C1 C2 Br1 113.1(2) . . ? C2 C3 C4 130.4(3) . . ? C5 C4 C3 128.3(3) . . ? C4 C5 C6 127.7(3) . . ? C7 C6 C5 131.0(3) . . ? C6 C7 C1 129.4(3) . . ? C6 C7 C9' 118.2(3) . . ? C1 C7 C9' 112.4(2) . . ? C2' C1' C9'a 120.7(3) . . ? C1' C2' C3' 120.6(3) . . ? C4' C3' C2' 120.7(3) . . ? C3' C4' C4'a 120.8(3) . . ? C10' C4'a C4' 122.2(3) . . ? C10' C4'a C9'a 118.8(2) . . ? C4' C4'a C9'a 119.0(3) . . ? C6' C5' C10'a 120.6(3) . . ? C5' C6' C7' 120.7(3) . . ? C8' C7' C6' 120.8(3) . . ? C7' C8' C8'a 120.8(3) . . ? C9' C8'a C10'a 120.0(2) . . ? C9' C8'a C8' 122.1(3) . . ? C10'a C8'a C8' 117.9(3) . . ? C8'a C9' C9'a 120.5(2) . . ? C8'a C9' C7 119.5(2) . . ? C9'a C9' C7 119.9(2) . . ? C9' C9'a C4'a 119.7(2) . . ? C9' C9'a C1' 122.2(3) . . ? C4'a C9'a C1' 118.1(3) . . ? C4'a C10' C10'a 122.2(2) . . ? C4'a C10' C11' 118.8(3) . . ? C10'a C10' C11' 119.1(3) . . ? C10' C10'a C5' 122.2(3) . . ? C10' C10'a C8'a 118.6(2) . . ? C5' C10'a C8'a 119.2(3) . . ? N1 C11' C10' 178.4(4) . . ? 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 O1 C1 C2 C3 -174.4(4) . . . . ? C7 C1 C2 C3 6.5(5) . . . . ? O1 C1 C2 Br1 3.1(4) . . . . ? C7 C1 C2 Br1 -175.9(2) . . . . ? C1 C2 C3 C4 0.5(7) . . . . ? Br1 C2 C3 C4 -177.0(3) . . . . ? C2 C3 C4 C5 -3.3(7) . . . . ? C3 C4 C5 C6 -1.8(6) . . . . ? C4 C5 C6 C7 4.9(6) . . . . ? C5 C6 C7 C1 0.9(6) . . . . ? C5 C6 C7 C9' 178.2(3) . . . . ? O1 C1 C7 C6 173.3(3) . . . . ? C2 C1 C7 C6 -7.6(5) . . . . ? O1 C1 C7 C9' -4.1(4) . . . . ? C2 C1 C7 C9' 175.0(3) . . . . ? C9'a C1' C2' C3' 0.2(5) . . . . ? C1' C2' C3' C4' 0.8(5) . . . . ? C2' C3' C4' C4'a -0.8(5) . . . . ? C3' C4' C4'a C10' -179.7(3) . . . . ? C3' C4' C4'a C9'a -0.1(4) . . . . ? C10'a C5' C6' C7' 0.6(5) . . . . ? C5' C6' C7' C8' 0.8(5) . . . . ? C6' C7' C8' C8'a -1.2(5) . . . . ? C7' C8' C8'a C9' -179.7(3) . . . . ? C7' C8' C8'a C10'a 0.3(4) . . . . ? C10'a C8'a C9' C9'a -4.2(4) . . . . ? C8' C8'a C9' C9'a 175.8(2) . . . . ? C10'a C8'a C9' C7 172.7(2) . . . . ? C8' C8'a C9' C7 -7.3(4) . . . . ? C6 C7 C9' C8'a 105.8(3) . . . . ? C1 C7 C9' C8'a -76.5(3) . . . . ? C6 C7 C9' C9'a -77.3(3) . . . . ? C1 C7 C9' C9'a 100.4(3) . . . . ? C8'a C9' C9'a C4'a 3.8(4) . . . . ? C7 C9' C9'a C4'a -173.1(2) . . . . ? C8'a C9' C9'a C1' -176.4(2) . . . . ? C7 C9' C9'a C1' 6.7(4) . . . . ? C10' C4'a C9'a C9' 0.4(4) . . . . ? C4' C4'a C9'a C9' -179.2(2) . . . . ? C10' C4'a C9'a C1' -179.4(2) . . . . ? C4' C4'a C9'a C1' 1.0(4) . . . . ? C2' C1' C9'a C9' 179.2(3) . . . . ? C2' C1' C9'a C4'a -1.0(4) . . . . ? C4' C4'a C10' C10'a 175.4(3) . . . . ? C9'a C4'a C10' C10'a -4.2(4) . . . . ? C4' C4'a C10' C11' -4.7(4) . . . . ? C9'a C4'a C10' C11' 175.7(3) . . . . ? C4'a C10' C10'a C5' -176.8(2) . . . . ? C11' C10' C10'a C5' 3.3(4) . . . . ? C4'a C10' C10'a C8'a 3.8(4) . . . . ? C11' C10' C10'a C8'a -176.1(3) . . . . ? C6' C5' C10'a C10' 179.1(3) . . . . ? C6' C5' C10'a C8'a -1.5(4) . . . . ? C9' C8'a C10'a C10' 0.5(4) . . . . ? C8' C8'a C10'a C10' -179.6(2) . . . . ? C9' C8'a C10'a C5' -179.0(2) . . . . ? C8' C8'a C10'a C5' 1.0(4) . . . . ? C4'a C10' C11' N1 -77.9(133) . . . . ? C10'a C10' C11' N1 102.0(133) . . . . ? data_18 _database_code_CSD 203120 _audit_creation_method SHELXL _chemical_name_systematic ; 9-(3-Bromo-2-oxocycloheptatrienyl)-9- cyanoanthran-5-one ; _chemical_name_common ? _chemical_formula_moiety ; 2 (C22 H12 Br N O2), C6 H6 ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C50 H30 Br2 N2 O4' _chemical_formula_weight 882.58 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.6763 1.2805 '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 13.614(3) _cell_length_b 13.721(6) _cell_length_c 13.427(3) _cell_angle_alpha 104.95(2) _cell_angle_beta 108.12(2) _cell_angle_gamma 111.56(2) _cell_volume 2010.8(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 44 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method ? _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 2.952 _exptl_absorpt_correction_type ; empirical via \y scans (North, Phillips, & Mathews, 1968) ; _exptl_absorpt_correction_T_min 0.8354 _exptl_absorpt_correction_T_max 0.9972 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.8 _diffrn_reflns_number 7978 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 69.93 _reflns_number_total 7635 _reflns_number_observed 6938 _reflns_observed_criterion >2\s(I) _computing_data_collection ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_cell_refinement ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+( 0.0572P)^2^+1.6870P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7635 _refine_ls_number_parameters 524 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_obs 0.0457 _refine_ls_wR_factor_all 0.1275 _refine_ls_wR_factor_obs 0.1236 _refine_ls_goodness_of_fit_all 1.090 _refine_ls_goodness_of_fit_obs 1.112 _refine_ls_restrained_S_all 1.090 _refine_ls_restrained_S_obs 1.112 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 1.257 _refine_diff_density_min -.917 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.85098(4) 0.57686(3) 0.45198(3) 0.06811(15) Uani 1 d . . O1 O 0.7524(3) 0.4354(2) 0.8694(2) 0.0848(8) Uani 1 d . . O2 O 0.8284(2) 0.6038(2) 0.6614(2) 0.0509(5) Uani 1 d . . N1 N 0.7704(3) 0.8866(3) 0.9555(3) 0.0836(10) Uani 1 d . . C1 C 0.5539(3) 0.4241(3) 0.7115(3) 0.0602(8) Uani 1 d . . H1 H 0.5448(3) 0.3583(3) 0.7238(3) 0.072 Uiso 1 calc R . C2 C 0.4593(3) 0.4216(3) 0.6333(3) 0.0670(9) Uani 1 d . . H2 H 0.3865(3) 0.3541(3) 0.5925(3) 0.080 Uiso 1 calc R . C3 C 0.4715(3) 0.5197(3) 0.6147(3) 0.0610(8) Uani 1 d . . H3 H 0.4070(3) 0.5182(3) 0.5620(3) 0.073 Uiso 1 calc R . C4 C 0.5797(3) 0.6189(2) 0.6746(2) 0.0486(6) Uani 1 d . . H4 H 0.5877(3) 0.6845(2) 0.6623(2) 0.058 Uiso 1 calc R . C4A C 0.6773(2) 0.6227(2) 0.7532(2) 0.0397(5) Uani 1 d . . C5 C 1.0115(3) 0.8221(3) 0.9530(3) 0.0635(8) Uani 1 d . . H5 H 1.0238(3) 0.8887(3) 0.9414(3) 0.076 Uiso 1 calc R . C6 C 1.1052(3) 0.8179(3) 1.0264(3) 0.0776(10) Uani 1 d . . H6 H 1.1808(3) 0.8814(3) 1.0633(3) 0.093 Uiso 1 calc R . C7 C 1.0869(3) 0.7196(4) 1.0453(3) 0.0769(10) Uani 1 d . . H7 H 1.1503(3) 0.7172(4) 1.0952(3) 0.092 Uiso 1 calc R . C8 C 0.9767(3) 0.6264(3) 0.9910(3) 0.0638(8) Uani 1 d . . H8 H 0.9651(3) 0.5610(3) 1.0047(3) 0.077 Uiso 1 calc R . C8A C 0.8805(3) 0.6276(2) 0.9151(2) 0.0481(6) Uani 1 d . . C9 C 0.7639(3) 0.5223(2) 0.8538(3) 0.0544(7) Uani 1 d . . C9A C 0.6638(3) 0.5241(2) 0.7730(2) 0.0458(6) Uani 1 d . . C10 C 0.7958(2) 0.7347(2) 0.8170(2) 0.0400(5) Uani 1 d . . C10A C 0.8984(2) 0.7265(2) 0.8963(2) 0.0455(6) Uani 1 d . . C11 C 0.7805(3) 0.8206(2) 0.8949(3) 0.0525(7) Uani 1 d . . C1' C 0.8298(2) 0.7783(2) 0.7309(2) 0.0394(5) Uani 1 d . . C2' C 0.8403(2) 0.6925(2) 0.6492(2) 0.0390(5) Uani 1 d . . C3' C 0.8614(2) 0.7095(2) 0.5533(2) 0.0459(6) Uani 1 d . . C4' C 0.8899(3) 0.8020(3) 0.5273(3) 0.0614(8) Uani 1 d . . H4' H 0.9006(3) 0.7915(3) 0.4609(3) 0.074 Uiso 1 calc R . C5' C 0.9059(3) 0.9122(3) 0.5864(3) 0.0669(9) Uani 1 d . . H5' H 0.9311(3) 0.9662(3) 0.5573(3) 0.080 Uiso 1 calc R . C6' C 0.8892(3) 0.9484(3) 0.6788(3) 0.0638(8) Uani 1 d . . H6' H 0.9043(3) 1.0246(3) 0.7058(3) 0.077 Uiso 1 calc R . C7' C 0.8514(3) 0.8863(2) 0.7414(3) 0.0526(7) Uani 1 d . . H7' H 0.8393(3) 0.9263(2) 0.7995(3) 0.063 Uiso 1 calc R . Br21 Br 1.16044(4) 0.25392(4) 0.81576(4) 0.0859(2) Uani 1 d . . O21 O 0.6499(3) -0.1423(2) 0.3816(3) 0.0964(9) Uani 1 d . . O22 O 0.9373(2) 0.16214(15) 0.6183(2) 0.0494(4) Uani 1 d . . N21 N 0.6275(2) 0.2964(2) 0.4591(3) 0.0675(7) Uani 1 d . . C21 C 0.7481(3) -0.0121(3) 0.2752(3) 0.0708(9) Uani 1 d . . H21 H 0.7225(3) -0.0909(3) 0.2434(3) 0.085 Uiso 1 calc R . C22 C 0.7961(4) 0.0545(4) 0.2248(3) 0.0802(11) Uani 1 d . . H22 H 0.8028(4) 0.0211(4) 0.1592(3) 0.096 Uiso 1 calc R . C23 C 0.8345(3) 0.1712(3) 0.2719(3) 0.0734(10) Uani 1 d . . H23 H 0.8666(3) 0.2167(3) 0.2377(3) 0.088 Uiso 1 calc R . C24 C 0.8256(3) 0.2207(3) 0.3691(3) 0.0571(7) Uani 1 d . . H24 H 0.8520(3) 0.2997(3) 0.4002(3) 0.068 Uiso 1 calc R . C24A C 0.7778(2) 0.1549(2) 0.4216(2) 0.0427(5) Uani 1 d . . C25 C 0.6865(3) 0.1757(3) 0.6668(3) 0.0566(7) Uani 1 d . . H25 H 0.7104(3) 0.2541(3) 0.6995(3) 0.068 Uiso 1 calc R . C26 C 0.6308(3) 0.1033(4) 0.7105(3) 0.0744(10) Uani 1 d . . H26 H 0.6176(3) 0.1334(4) 0.7724(3) 0.089 Uiso 1 calc R . C27 C 0.5952(3) -0.0127(4) 0.6628(3) 0.0801(12) Uani 1 d . . H27 H 0.5594(3) -0.0604(4) 0.6934(3) 0.096 Uiso 1 calc R . C28 C 0.6123(3) -0.0578(3) 0.5706(3) 0.0681(9) Uani 1 d . . H28 H 0.5868(3) -0.1365(3) 0.5379(3) 0.082 Uiso 1 calc R . C28A C 0.6676(2) 0.0129(2) 0.5246(3) 0.0505(6) Uani 1 d . . C29 C 0.6831(3) -0.0387(2) 0.4245(3) 0.0607(8) Uani 1 d . . C29A C 0.7369(3) 0.0362(2) 0.3734(2) 0.0516(6) Uani 1 d . . C30 C 0.7683(2) 0.2141(2) 0.5293(2) 0.0387(5) Uani 1 d . . C30A C 0.7062(2) 0.1313(2) 0.5749(2) 0.0430(6) Uani 1 d . . C31 C 0.6905(2) 0.2634(2) 0.4911(2) 0.0467(6) Uani 1 d . . C21' C 0.8915(2) 0.3104(2) 0.6270(2) 0.0362(5) Uani 1 d . . C22' C 0.9707(2) 0.2653(2) 0.6688(2) 0.0379(5) Uani 1 d . . C23' C 1.0869(2) 0.3391(2) 0.7700(2) 0.0451(6) Uani 1 d . . C24' C 1.1506(3) 0.4544(3) 0.8330(2) 0.0542(7) Uani 1 d . . H24' H 1.2243(3) 0.4810(3) 0.8928(2) 0.065 Uiso 1 calc R . C25' C 1.1214(3) 0.5402(3) 0.8209(3) 0.0607(8) Uani 1 d . . H25' H 1.1801(3) 0.6162(3) 0.8700(3) 0.073 Uiso 1 calc R . C26' C 1.0195(3) 0.5262(2) 0.7476(3) 0.0598(8) Uani 1 d . . H26' H 1.0164(3) 0.5939(2) 0.7532(3) 0.072 Uiso 1 calc R . C27' C 0.9155(2) 0.4225(2) 0.6626(3) 0.0479(6) Uani 1 d . . H27' H 0.8527(2) 0.4328(2) 0.6245(3) 0.057 Uiso 1 calc R . C1" C 0.5363(7) 0.2487(7) 0.9397(6) 0.140(3) Uani 1 d . . H1" H 0.5289(7) 0.2376(7) 0.8659(6) 0.168 Uiso 1 calc R . C2" C 0.5580(7) 0.1785(7) 0.9840(7) 0.144(3) Uani 1 d . . H2" H 0.5629(7) 0.1175(7) 0.9399(7) 0.173 Uiso 1 calc R . C3" C 0.5733(6) 0.1952(8) 1.0954(8) 0.144(3) Uani 1 d . . H3" H 0.5882(6) 0.1464(8) 1.1272(8) 0.172 Uiso 1 calc R . C4" C 0.5655(7) 0.2872(10) 1.1567(6) 0.151(3) Uani 1 d . . H4" H 0.5784(7) 0.3031(10) 1.2327(6) 0.182 Uiso 1 calc R . C5" C 0.5395(8) 0.3536(8) 1.1081(8) 0.155(3) Uani 1 d . . H5" H 0.5313(8) 0.4134(8) 1.1493(8) 0.186 Uiso 1 calc R . C6" C 0.5252(6) 0.3344(7) 0.9988(7) 0.140(2) Uani 1 d . . H6" H 0.5075(6) 0.3811(7) 0.9654(7) 0.168 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0871(3) 0.0629(2) 0.0641(2) 0.0237(2) 0.0518(2) 0.0334(2) O1 0.097(2) 0.0541(13) 0.097(2) 0.0474(14) 0.025(2) 0.0362(13) O2 0.0773(13) 0.0433(10) 0.0532(11) 0.0268(9) 0.0375(10) 0.0384(10) N1 0.106(3) 0.060(2) 0.081(2) 0.011(2) 0.054(2) 0.040(2) C1 0.064(2) 0.0413(15) 0.071(2) 0.0266(14) 0.032(2) 0.0196(14) C2 0.051(2) 0.051(2) 0.078(2) 0.022(2) 0.024(2) 0.0135(14) C3 0.048(2) 0.061(2) 0.066(2) 0.024(2) 0.0202(14) 0.0245(14) C4 0.052(2) 0.0483(15) 0.053(2) 0.0248(12) 0.0253(13) 0.0285(13) C4A 0.0488(14) 0.0357(12) 0.0392(12) 0.0164(10) 0.0237(11) 0.0214(11) C5 0.061(2) 0.053(2) 0.051(2) 0.0177(14) 0.0095(14) 0.0205(15) C6 0.057(2) 0.072(2) 0.062(2) 0.016(2) 0.001(2) 0.021(2) C7 0.070(2) 0.092(3) 0.054(2) 0.028(2) 0.007(2) 0.045(2) C8 0.081(2) 0.071(2) 0.049(2) 0.031(2) 0.023(2) 0.047(2) C8A 0.063(2) 0.0501(15) 0.0363(13) 0.0203(11) 0.0215(12) 0.0321(13) C9 0.074(2) 0.0451(15) 0.054(2) 0.0271(13) 0.0293(15) 0.0328(14) C9A 0.055(2) 0.0380(13) 0.0478(14) 0.0204(11) 0.0257(12) 0.0226(12) C10 0.0504(14) 0.0329(12) 0.0374(12) 0.0138(10) 0.0196(11) 0.0216(11) C10A 0.0536(15) 0.0431(13) 0.0351(12) 0.0155(11) 0.0158(11) 0.0233(12) C11 0.065(2) 0.0404(14) 0.050(2) 0.0141(12) 0.0290(14) 0.0250(13) C1' 0.0425(13) 0.0343(12) 0.0425(13) 0.0187(10) 0.0178(11) 0.0192(10) C2' 0.0393(12) 0.0383(12) 0.0415(13) 0.0197(10) 0.0169(10) 0.0201(10) C3' 0.0441(14) 0.0506(15) 0.0487(14) 0.0244(12) 0.0252(12) 0.0225(12) C4' 0.070(2) 0.074(2) 0.070(2) 0.048(2) 0.046(2) 0.039(2) C5' 0.075(2) 0.064(2) 0.098(3) 0.060(2) 0.053(2) 0.039(2) C6' 0.076(2) 0.047(2) 0.091(2) 0.045(2) 0.045(2) 0.036(2) C7' 0.065(2) 0.0397(14) 0.064(2) 0.0264(13) 0.0331(15) 0.0295(13) Br21 0.0720(3) 0.0825(3) 0.0858(3) 0.0318(2) 0.0044(2) 0.0494(2) O21 0.130(3) 0.0340(12) 0.108(2) 0.0218(13) 0.053(2) 0.0303(14) O22 0.0494(10) 0.0349(9) 0.0564(11) 0.0177(8) 0.0141(9) 0.0225(8) N21 0.0513(14) 0.059(2) 0.087(2) 0.0346(15) 0.0170(14) 0.0309(13) C21 0.074(2) 0.054(2) 0.061(2) 0.004(2) 0.023(2) 0.030(2) C22 0.085(3) 0.086(3) 0.056(2) 0.014(2) 0.036(2) 0.035(2) C23 0.080(2) 0.080(2) 0.054(2) 0.028(2) 0.034(2) 0.029(2) C24 0.062(2) 0.051(2) 0.050(2) 0.0230(13) 0.0231(14) 0.0206(14) C24A 0.0410(13) 0.0390(13) 0.0380(12) 0.0133(10) 0.0106(10) 0.0177(11) C25 0.0461(15) 0.058(2) 0.046(2) 0.0173(13) 0.0152(12) 0.0150(13) C26 0.049(2) 0.098(3) 0.051(2) 0.029(2) 0.0195(14) 0.015(2) C27 0.049(2) 0.087(3) 0.073(2) 0.048(2) 0.017(2) 0.003(2) C28 0.050(2) 0.053(2) 0.077(2) 0.037(2) 0.015(2) 0.0072(14) C28A 0.0402(13) 0.0397(14) 0.057(2) 0.0241(12) 0.0114(12) 0.0118(11) C29 0.059(2) 0.0352(14) 0.067(2) 0.0158(13) 0.0149(15) 0.0174(13) C29A 0.0497(15) 0.0390(13) 0.0486(15) 0.0096(11) 0.0126(12) 0.0190(12) C30 0.0374(12) 0.0317(11) 0.0407(12) 0.0144(10) 0.0121(10) 0.0160(10) C30A 0.0319(12) 0.0399(13) 0.0425(13) 0.0177(11) 0.0084(10) 0.0104(10) C31 0.0403(13) 0.0377(13) 0.0518(15) 0.0182(11) 0.0128(11) 0.0163(11) C21' 0.0348(11) 0.0303(11) 0.0388(12) 0.0132(9) 0.0149(10) 0.0138(9) C22' 0.0380(12) 0.0363(12) 0.0416(12) 0.0204(10) 0.0182(10) 0.0175(10) C23' 0.0415(13) 0.0511(15) 0.0429(13) 0.0209(12) 0.0167(11) 0.0240(12) C24' 0.0408(14) 0.056(2) 0.0445(14) 0.0135(13) 0.0109(12) 0.0151(13) C25' 0.047(2) 0.0381(14) 0.065(2) 0.0052(13) 0.0170(14) 0.0082(12) C26' 0.053(2) 0.0309(13) 0.075(2) 0.0107(13) 0.020(2) 0.0163(12) C27' 0.0411(13) 0.0338(12) 0.058(2) 0.0141(11) 0.0153(12) 0.0180(11) C1" 0.140(6) 0.134(6) 0.084(4) 0.016(4) 0.046(4) 0.030(5) C2" 0.165(7) 0.128(6) 0.113(5) 0.032(4) 0.077(5) 0.047(5) C3" 0.093(4) 0.183(8) 0.158(7) 0.090(6) 0.056(4) 0.058(5) C4" 0.130(6) 0.219(10) 0.101(5) 0.053(5) 0.066(4) 0.081(6) C5" 0.155(7) 0.191(8) 0.154(7) 0.069(6) 0.107(6) 0.090(6) C6" 0.106(4) 0.164(7) 0.137(6) 0.062(5) 0.060(4) 0.049(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 Br1 C3' 1.896(3) . ? O1 C9 1.226(3) . ? O2 C2' 1.228(3) . ? N1 C11 1.133(4) . ? C1 C2 1.368(5) . ? C1 C9A 1.393(4) . ? C2 C3 1.391(5) . ? C3 C4 1.377(4) . ? C4 C4A 1.389(4) . ? C4A C9A 1.402(4) . ? C4A C10 1.528(4) . ? C5 C6 1.379(5) . ? C5 C10A 1.393(4) . ? C6 C7 1.384(6) . ? C7 C8 1.359(6) . ? C8 C8A 1.395(4) . ? C8A C10A 1.392(4) . ? C8A C9 1.474(4) . ? C9 C9A 1.467(4) . ? C10 C11 1.486(4) . ? C10 C10A 1.533(4) . ? C10 C1' 1.548(3) . ? C1' C7' 1.360(4) . ? C1' C2' 1.470(4) . ? C2' C3' 1.461(4) . ? C3' C4' 1.355(4) . ? C4' C5' 1.413(5) . ? C5' C6' 1.332(5) . ? C6' C7' 1.419(4) . ? Br21 C23' 1.895(3) . ? O21 C29 1.224(4) . ? O22 C22' 1.229(3) . ? N21 C31 1.133(4) . ? C21 C22 1.370(6) . ? C21 C29A 1.397(5) . ? C22 C23 1.376(6) . ? C23 C24 1.371(5) . ? C24 C24A 1.385(4) . ? C24A C29A 1.395(4) . ? C24A C30 1.534(4) . ? C25 C30A 1.380(4) . ? C25 C26 1.389(5) . ? C26 C27 1.375(6) . ? C27 C28 1.364(6) . ? C28 C28A 1.396(4) . ? C28A C30A 1.400(4) . ? C28A C29 1.465(5) . ? C29 C29A 1.479(5) . ? C30 C31 1.486(3) . ? C30 C30A 1.534(3) . ? C30 C21' 1.546(3) . ? C21' C27' 1.363(3) . ? C21' C22' 1.468(3) . ? C22' C23' 1.467(4) . ? C23' C24' 1.348(4) . ? C24' C25' 1.404(5) . ? C25' C26' 1.337(5) . ? C26' C27' 1.417(4) . ? C1" C6" 1.326(10) . ? C1" C2" 1.328(10) . ? C2" C3" 1.388(10) . ? C3" C4" 1.378(11) . ? C4" C5" 1.334(11) . ? C5" C6" 1.358(10) . ? 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 C2 C1 C9A 120.8(3) . . ? C1 C2 C3 120.2(3) . . ? C4 C3 C2 119.6(3) . . ? C3 C4 C4A 121.1(3) . . ? C4 C4A C9A 119.0(2) . . ? C4 C4A C10 119.1(2) . . ? C9A C4A C10 121.9(2) . . ? C6 C5 C10A 120.0(3) . . ? C5 C6 C7 120.2(3) . . ? C8 C7 C6 120.1(3) . . ? C7 C8 C8A 121.0(3) . . ? C10A C8A C8 119.1(3) . . ? C10A C8A C9 122.0(3) . . ? C8 C8A C9 118.9(3) . . ? O1 C9 C9A 121.5(3) . . ? O1 C9 C8A 120.1(3) . . ? C9A C9 C8A 118.4(2) . . ? C1 C9A C4A 119.3(3) . . ? C1 C9A C9 119.1(3) . . ? C4A C9A C9 121.6(3) . . ? C11 C10 C4A 106.5(2) . . ? C11 C10 C10A 105.3(2) . . ? C4A C10 C10A 114.4(2) . . ? C11 C10 C1' 110.1(2) . . ? C4A C10 C1' 110.9(2) . . ? C10A C10 C1' 109.4(2) . . ? C8A C10A C5 119.7(3) . . ? C8A C10A C10 121.6(2) . . ? C5 C10A C10 118.7(2) . . ? N1 C11 C10 179.0(4) . . ? C7' C1' C2' 128.7(2) . . ? C7' C1' C10 119.9(2) . . ? C2' C1' C10 111.3(2) . . ? O2 C2' C3' 119.8(2) . . ? O2 C2' C1' 118.7(2) . . ? C3' C2' C1' 121.5(2) . . ? C4' C3' C2' 131.8(3) . . ? C4' C3' Br1 116.2(2) . . ? C2' C3' Br1 112.0(2) . . ? C3' C4' C5' 129.4(3) . . ? C6' C5' C4' 128.0(3) . . ? C5' C6' C7' 128.6(3) . . ? C1' C7' C6' 131.1(3) . . ? C22 C21 C29A 121.2(3) . . ? C21 C22 C23 119.4(3) . . ? C24 C23 C22 120.4(3) . . ? C23 C24 C24A 121.0(3) . . ? C24 C24A C29A 119.0(3) . . ? C24 C24A C30 119.0(2) . . ? C29A C24A C30 121.9(2) . . ? C30A C25 C26 119.9(3) . . ? C27 C26 C25 120.5(4) . . ? C28 C27 C26 120.1(3) . . ? C27 C28 C28A 120.8(3) . . ? C28 C28A C30A 119.1(3) . . ? C28 C28A C29 119.3(3) . . ? C30A C28A C29 121.6(3) . . ? O21 C29 C28A 121.1(3) . . ? O21 C29 C29A 120.1(3) . . ? C28A C29 C29A 118.7(2) . . ? C24A C29A C21 118.9(3) . . ? C24A C29A C29 121.5(3) . . ? C21 C29A C29 119.6(3) . . ? C31 C30 C30A 105.5(2) . . ? C31 C30 C24A 105.3(2) . . ? C30A C30 C24A 114.3(2) . . ? C31 C30 C21' 110.7(2) . . ? C30A C30 C21' 109.8(2) . . ? C24A C30 C21' 110.9(2) . . ? C25 C30A C28A 119.7(3) . . ? C25 C30A C30 118.5(2) . . ? C28A C30A C30 121.9(2) . . ? N21 C31 C30 177.1(3) . . ? C27' C21' C22' 128.0(2) . . ? C27' C21' C30 119.4(2) . . ? C22' C21' C30 112.6(2) . . ? O22 C22' C23' 119.3(2) . . ? O22 C22' C21' 118.7(2) . . ? C23' C22' C21' 122.0(2) . . ? C24' C23' C22' 132.0(3) . . ? C24' C23' Br21 115.5(2) . . ? C22' C23' Br21 112.6(2) . . ? C23' C24' C25' 129.2(3) . . ? C26' C25' C24' 128.0(3) . . ? C25' C26' C27' 129.0(3) . . ? C21' C27' C26' 131.1(3) . . ? C6" C1" C2" 121.3(8) . . ? C1" C2" C3" 120.6(8) . . ? C4" C3" C2" 117.1(8) . . ? C5" C4" C3" 120.7(8) . . ? C4" C5" C6" 120.4(9) . . ? C1" C6" C5" 119.8(9) . . ? 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 -0.4(5) . . . . ? C1 C2 C3 C4 0.6(5) . . . . ? C2 C3 C4 C4A 0.3(5) . . . . ? C3 C4 C4A C9A -1.4(4) . . . . ? C3 C4 C4A C10 179.5(3) . . . . ? C10A C5 C6 C7 -1.0(6) . . . . ? C5 C6 C7 C8 0.4(6) . . . . ? C6 C7 C8 C8A 0.5(6) . . . . ? C7 C8 C8A C10A -0.8(5) . . . . ? C7 C8 C8A C9 176.9(3) . . . . ? C10A C8A C9 O1 177.4(3) . . . . ? C8 C8A C9 O1 -0.3(5) . . . . ? C10A C8A C9 C9A -1.6(4) . . . . ? C8 C8A C9 C9A -179.2(3) . . . . ? C2 C1 C9A C4A -0.7(5) . . . . ? C2 C1 C9A C9 -178.4(3) . . . . ? C4 C4A C9A C1 1.5(4) . . . . ? C10 C4A C9A C1 -179.4(3) . . . . ? C4 C4A C9A C9 179.2(3) . . . . ? C10 C4A C9A C9 -1.8(4) . . . . ? O1 C9 C9A C1 -1.0(5) . . . . ? C8A C9 C9A C1 177.9(3) . . . . ? O1 C9 C9A C4A -178.7(3) . . . . ? C8A C9 C9A C4A 0.2(4) . . . . ? C4 C4A C10 C11 67.3(3) . . . . ? C9A C4A C10 C11 -111.7(3) . . . . ? C4 C4A C10 C10A -176.8(2) . . . . ? C9A C4A C10 C10A 4.2(3) . . . . ? C4 C4A C10 C1' -52.5(3) . . . . ? C9A C4A C10 C1' 128.5(2) . . . . ? C8 C8A C10A C5 0.2(4) . . . . ? C9 C8A C10A C5 -177.4(3) . . . . ? C8 C8A C10A C10 -178.0(3) . . . . ? C9 C8A C10A C10 4.4(4) . . . . ? C6 C5 C10A C8A 0.7(5) . . . . ? C6 C5 C10A C10 178.9(3) . . . . ? C11 C10 C10A C8A 111.1(3) . . . . ? C4A C10 C10A C8A -5.4(4) . . . . ? C1' C10 C10A C8A -130.5(3) . . . . ? C11 C10 C10A C5 -67.1(3) . . . . ? C4A C10 C10A C5 176.3(3) . . . . ? C1' C10 C10A C5 51.2(3) . . . . ? C11 C10 C1' C7' 5.7(4) . . . . ? C4A C10 C1' C7' 123.3(3) . . . . ? C10A C10 C1' C7' -109.6(3) . . . . ? C11 C10 C1' C2' -177.4(2) . . . . ? C4A C10 C1' C2' -59.8(3) . . . . ? C10A C10 C1' C2' 67.3(3) . . . . ? C7' C1' C2' O2 172.6(3) . . . . ? C10 C1' C2' O2 -3.9(3) . . . . ? C7' C1' C2' C3' -8.9(4) . . . . ? C10 C1' C2' C3' 174.6(2) . . . . ? O2 C2' C3' C4' -171.8(3) . . . . ? C1' C2' C3' C4' 9.7(5) . . . . ? O2 C2' C3' Br1 5.9(3) . . . . ? C1' C2' C3' Br1 -172.6(2) . . . . ? C2' C3' C4' C5' -1.4(6) . . . . ? Br1 C3' C4' C5' -179.0(3) . . . . ? C3' C4' C5' C6' -4.5(7) . . . . ? C4' C5' C6' C7' 0.0(7) . . . . ? C2' C1' C7' C6' 0.2(6) . . . . ? C10 C1' C7' C6' 176.5(3) . . . . ? C5' C6' C7' C1' 5.1(7) . . . . ? C29A C21 C22 C23 0.2(6) . . . . ? C21 C22 C23 C24 0.5(6) . . . . ? C22 C23 C24 C24A -0.2(6) . . . . ? C23 C24 C24A C29A -0.8(5) . . . . ? C23 C24 C24A C30 -179.2(3) . . . . ? C30A C25 C26 C27 0.0(5) . . . . ? C25 C26 C27 C28 -1.3(5) . . . . ? C26 C27 C28 C28A 1.1(5) . . . . ? C27 C28 C28A C30A 0.4(5) . . . . ? C27 C28 C28A C29 -179.2(3) . . . . ? C28 C28A C29 O21 -1.0(5) . . . . ? C30A C28A C29 O21 179.4(3) . . . . ? C28 C28A C29 C29A 177.2(3) . . . . ? C30A C28A C29 C29A -2.3(4) . . . . ? C24 C24A C29A C21 1.5(4) . . . . ? C30 C24A C29A C21 179.9(3) . . . . ? C24 C24A C29A C29 -178.9(3) . . . . ? C30 C24A C29A C29 -0.5(4) . . . . ? C22 C21 C29A C24A -1.2(5) . . . . ? C22 C21 C29A C29 179.2(3) . . . . ? O21 C29 C29A C24A -178.7(3) . . . . ? C28A C29 C29A C24A 3.0(4) . . . . ? O21 C29 C29A C21 0.9(5) . . . . ? C28A C29 C29A C21 -177.4(3) . . . . ? C24 C24A C30 C31 60.6(3) . . . . ? C29A C24A C30 C31 -117.8(3) . . . . ? C24 C24A C30 C30A 176.0(2) . . . . ? C29A C24A C30 C30A -2.4(3) . . . . ? C24 C24A C30 C21' -59.2(3) . . . . ? C29A C24A C30 C21' 122.4(3) . . . . ? C26 C25 C30A C28A 1.4(4) . . . . ? C26 C25 C30A C30 -179.8(3) . . . . ? C28 C28A C30A C25 -1.6(4) . . . . ? C29 C28A C30A C25 178.0(3) . . . . ? C28 C28A C30A C30 179.6(3) . . . . ? C29 C28A C30A C30 -0.8(4) . . . . ? C31 C30 C30A C25 -60.4(3) . . . . ? C24A C30 C30A C25 -175.7(2) . . . . ? C21' C30 C30A C25 58.9(3) . . . . ? C31 C30 C30A C28A 118.4(3) . . . . ? C24A C30 C30A C28A 3.1(3) . . . . ? C21' C30 C30A C28A -122.3(3) . . . . ? C31 C30 C21' C27' -2.1(3) . . . . ? C30A C30 C21' C27' -118.1(3) . . . . ? C24A C30 C21' C27' 114.5(3) . . . . ? C31 C30 C21' C22' 179.1(2) . . . . ? C30A C30 C21' C22' 63.0(3) . . . . ? C24A C30 C21' C22' -64.3(3) . . . . ? C27' C21' C22' O22 -172.8(3) . . . . ? C30 C21' C22' O22 5.9(3) . . . . ? C27' C21' C22' C23' 8.6(4) . . . . ? C30 C21' C22' C23' -172.7(2) . . . . ? O22 C22' C23' C24' 171.6(3) . . . . ? C21' C22' C23' C24' -9.8(5) . . . . ? O22 C22' C23' Br21 -6.4(3) . . . . ? C21' C22' C23' Br21 172.2(2) . . . . ? C22' C23' C24' C25' 1.9(6) . . . . ? Br21 C23' C24' C25' 179.8(3) . . . . ? C23' C24' C25' C26' 4.4(6) . . . . ? C24' C25' C26' C27' -0.8(6) . . . . ? C22' C21' C27' C26' -0.4(5) . . . . ? C30 C21' C27' C26' -179.0(3) . . . . ? C25' C26' C27' C21' -4.1(6) . . . . ? C6" C1" C2" C3" -2.1(13) . . . . ? C1" C2" C3" C4" -0.2(12) . . . . ? C2" C3" C4" C5" 2.6(12) . . . . ? C3" C4" C5" C6" -2.7(13) . . . . ? C2" C1" C6" C5" 2.0(12) . . . . ? C4" C5" C6" C1" 0.4(12) . . . . ? data_19 _database_code_CSD 203121 _audit_creation_method SHELXL _chemical_name_systematic ; 9-(6-Bromo-7-oxocycloheptatrienyl)- 9,10-dicyano-10-(4,5,6-tribromocyclohex-2-enyl)- 9,10-dihydroanthracene ; _chemical_name_common ? _chemical_formula_moiety 'C29 H18 Br4 N2 O' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C29 H18 Br4 N2 O' _chemical_formula_weight 730.09 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.6763 1.2805 '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 1 21/n 1' 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 11.026(2) _cell_length_b 23.928(4) _cell_length_c 9.7068(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.854(12) _cell_angle_gamma 90.00 _cell_volume 2559.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.41 _cell_measurement_theta_max 42.47 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method ? _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 7.887 _exptl_absorpt_correction_type ; empirical via \y scans (North, Phillips, & Mathews, 1968) ; _exptl_absorpt_correction_T_min 0.7266 _exptl_absorpt_correction_T_max 0.9939 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0.9 _diffrn_reflns_number 5148 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 70.01 _reflns_number_total 4854 _reflns_number_observed 4341 _reflns_observed_criterion >2\s(I) _computing_data_collection ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_cell_refinement ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+( 0.0722P)^2^+11.1122P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4854 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_obs 0.0530 _refine_ls_wR_factor_all 0.1441 _refine_ls_wR_factor_obs 0.1394 _refine_ls_goodness_of_fit_all 1.063 _refine_ls_goodness_of_fit_obs 1.091 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.091 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 1.815 _refine_diff_density_min -1.174 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br -0.20575(7) 0.82891(3) 0.77227(8) 0.0570(2) Uani 1 d . . Br2 Br 0.69606(5) 0.48956(3) 0.68870(8) 0.0485(2) Uani 1 d . . Br3 Br 0.44766(6) 0.43284(2) 0.84615(7) 0.0474(2) Uani 1 d . . Br4 Br 0.18029(5) 0.48668(2) 0.70976(7) 0.0432(2) Uani 1 d . . O1 O -0.0497(4) 0.7316(2) 0.7798(4) 0.0469(10) Uani 1 d . . N1 N 0.0678(5) 0.5796(2) 0.4137(5) 0.0463(12) Uani 1 d . . N2 N 0.4325(4) 0.6537(2) 0.9460(5) 0.0424(11) Uani 1 d . . C1 C 0.1149(5) 0.7437(2) 0.5191(6) 0.0346(11) Uani 1 d . . H1 H 0.0429(5) 0.7484(2) 0.4679(6) 0.042 Uiso 1 calc R . C2 C 0.2042(5) 0.7841(2) 0.5139(6) 0.0409(13) Uani 1 d . . H2 H 0.1911(5) 0.8161(2) 0.4611(6) 0.049 Uiso 1 calc R . C3 C 0.3114(5) 0.7772(2) 0.5859(6) 0.0390(12) Uani 1 d . . H3 H 0.3716(5) 0.8043(2) 0.5819(6) 0.047 Uiso 1 calc R . C4 C 0.3301(4) 0.7294(2) 0.6654(5) 0.0306(10) Uani 1 d . . H4 H 0.4034(4) 0.7247(2) 0.7143(5) 0.037 Uiso 1 calc R . C4a C 0.2415(4) 0.6888(2) 0.6727(5) 0.0232(9) Uani 1 d . . C5 C 0.1437(4) 0.5955(2) 0.9565(5) 0.0295(10) Uani 1 d . . H5 H 0.2159(4) 0.5936(2) 1.0084(5) 0.035 Uiso 1 calc R . C6 C 0.0372(5) 0.5756(2) 1.0122(6) 0.0400(12) Uani 1 d . . H6 H 0.0374(5) 0.5616(2) 1.1015(6) 0.048 Uiso 1 calc R . C7 C -0.0684(5) 0.5771(3) 0.9328(7) 0.0450(14) Uani 1 d . . H7 H -0.1392(5) 0.5622(3) 0.9671(7) 0.054 Uiso 1 calc R . C8 C -0.0701(5) 0.6004(2) 0.8031(6) 0.0372(12) Uani 1 d . . H8 H -0.1424(5) 0.6012(2) 0.7512(6) 0.045 Uiso 1 calc R . C8a C 0.0341(4) 0.6228(2) 0.7483(5) 0.0263(9) Uani 1 d . . C9 C 0.0289(4) 0.6529(2) 0.6092(5) 0.0244(9) Uani 1 d . . C9a C 0.1311(4) 0.6963(2) 0.5994(5) 0.0235(9) Uani 1 d . . C10 C 0.2618(4) 0.6361(2) 0.7586(5) 0.0215(9) Uani 1 d . . C10a C 0.1439(4) 0.6182(2) 0.8246(5) 0.0236(9) Uani 1 d . . C11 C 0.0503(4) 0.6110(2) 0.4987(5) 0.0297(10) Uani 1 d . . C12 C 0.3553(4) 0.6471(2) 0.8681(5) 0.0275(10) Uani 1 d . . C1' C -0.0967(4) 0.6805(2) 0.5827(5) 0.0266(9) Uani 1 d . . C2' C -0.1714(5) 0.6607(2) 0.4792(6) 0.0369(12) Uani 1 d . . H2' H -0.1387(5) 0.6318(2) 0.4281(6) 0.044 Uiso 1 calc R . C3' C -0.2920(5) 0.6769(3) 0.4356(7) 0.049(2) Uani 1 d . . H3' H -0.3294(5) 0.6548(3) 0.3678(7) 0.058 Uiso 1 calc R . C4' C -0.3575(5) 0.7203(3) 0.4813(7) 0.051(2) Uani 1 d . . H4' H -0.4356(5) 0.7238(3) 0.4432(7) 0.061 Uiso 1 calc R . C5' C -0.3227(5) 0.7606(3) 0.5785(7) 0.048(2) Uani 1 d . . H5' H -0.3779(5) 0.7897(3) 0.5882(7) 0.057 Uiso 1 calc R . C6' C -0.2218(5) 0.7644(2) 0.6611(6) 0.0365(12) Uani 1 d . . C7' C -0.1207(4) 0.7254(2) 0.6817(5) 0.0296(10) Uani 1 d . . C1" C 0.3157(4) 0.5867(2) 0.6674(5) 0.0237(9) Uani 1 d . . H1" H 0.2600(4) 0.5805(2) 0.5882(5) 0.028 Uiso 1 calc R . C2" C 0.4361(4) 0.6051(2) 0.6137(5) 0.0317(10) Uani 1 d . . H2" H 0.4362(4) 0.6348(2) 0.5521(5) 0.038 Uiso 1 calc R . C3" C 0.5412(5) 0.5820(2) 0.6479(6) 0.0367(12) Uani 1 d . . H3" H 0.6115(5) 0.5977(2) 0.6142(6) 0.044 Uiso 1 calc R . C4" C 0.5522(5) 0.5319(2) 0.7381(5) 0.0327(11) Uani 1 d . . H4" H 0.5613(5) 0.5440(2) 0.8344(5) 0.039 Uiso 1 calc R . C5" C 0.4380(4) 0.4968(2) 0.7206(5) 0.0289(10) Uani 1 d . . H5" H 0.4318(4) 0.4831(2) 0.6255(5) 0.035 Uiso 1 calc R . C6" C 0.3262(4) 0.5314(2) 0.7494(5) 0.0257(9) Uani 1 d . . H6" H 0.3283(4) 0.5407(2) 0.8478(5) 0.031 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0773(5) 0.0373(4) 0.0574(4) -0.0005(3) 0.0193(3) 0.0159(3) Br2 0.0310(3) 0.0432(4) 0.0711(4) -0.0038(3) -0.0020(3) 0.0098(2) Br3 0.0581(4) 0.0290(3) 0.0549(4) 0.0131(2) 0.0005(3) 0.0067(3) Br4 0.0341(3) 0.0300(3) 0.0656(4) -0.0005(2) 0.0055(3) -0.0108(2) O1 0.037(2) 0.054(3) 0.049(2) -0.021(2) -0.008(2) 0.010(2) N1 0.044(3) 0.049(3) 0.047(3) -0.014(2) 0.003(2) -0.001(2) N2 0.037(2) 0.042(3) 0.048(3) 0.005(2) -0.011(2) -0.009(2) C1 0.027(2) 0.030(3) 0.048(3) 0.010(2) 0.004(2) 0.008(2) C2 0.037(3) 0.026(3) 0.060(3) 0.014(2) 0.008(2) 0.004(2) C3 0.032(3) 0.025(2) 0.061(3) 0.007(2) 0.009(2) -0.005(2) C4 0.024(2) 0.024(2) 0.044(3) 0.000(2) 0.002(2) -0.003(2) C4a 0.021(2) 0.020(2) 0.029(2) -0.001(2) 0.004(2) 0.001(2) C5 0.029(2) 0.027(2) 0.033(2) 0.002(2) 0.000(2) -0.003(2) C6 0.046(3) 0.040(3) 0.035(3) 0.008(2) 0.011(2) -0.005(2) C7 0.033(3) 0.048(3) 0.054(3) 0.012(3) 0.013(2) -0.009(2) C8 0.023(2) 0.038(3) 0.050(3) 0.006(2) 0.000(2) -0.008(2) C8a 0.024(2) 0.022(2) 0.032(2) -0.001(2) 0.001(2) -0.001(2) C9 0.020(2) 0.022(2) 0.031(2) -0.003(2) -0.001(2) 0.000(2) C9a 0.019(2) 0.021(2) 0.030(2) -0.001(2) 0.003(2) 0.002(2) C10 0.017(2) 0.020(2) 0.027(2) 0.000(2) -0.002(2) -0.002(2) C10a 0.021(2) 0.021(2) 0.029(2) -0.001(2) 0.002(2) -0.003(2) C11 0.026(2) 0.028(2) 0.035(3) -0.001(2) -0.001(2) 0.000(2) C12 0.026(2) 0.023(2) 0.033(2) 0.001(2) -0.002(2) -0.002(2) C1' 0.018(2) 0.030(2) 0.031(2) 0.002(2) -0.001(2) -0.001(2) C2' 0.029(3) 0.042(3) 0.039(3) -0.002(2) -0.006(2) -0.002(2) C3' 0.031(3) 0.060(4) 0.054(4) 0.011(3) -0.019(3) -0.014(3) C4' 0.024(3) 0.057(4) 0.071(4) 0.031(3) -0.011(3) 0.000(3) C5' 0.028(3) 0.041(3) 0.073(4) 0.025(3) -0.001(3) 0.012(2) C6' 0.034(3) 0.031(3) 0.045(3) 0.012(2) 0.012(2) 0.002(2) C7' 0.020(2) 0.032(3) 0.037(3) 0.000(2) 0.003(2) 0.002(2) C1" 0.023(2) 0.021(2) 0.027(2) -0.001(2) 0.000(2) 0.001(2) C2" 0.029(2) 0.024(2) 0.042(3) 0.008(2) 0.009(2) 0.001(2) C3" 0.028(3) 0.033(3) 0.050(3) 0.003(2) 0.009(2) -0.001(2) C4" 0.031(2) 0.030(2) 0.038(3) -0.001(2) 0.000(2) 0.006(2) C5" 0.034(3) 0.023(2) 0.029(2) 0.003(2) -0.001(2) 0.004(2) C6" 0.026(2) 0.019(2) 0.032(2) 0.004(2) 0.001(2) -0.002(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 Br1 C6' 1.888(6) . ? Br2 C4" 1.955(5) . ? Br3 C5" 1.958(5) . ? Br4 C6" 1.960(5) . ? O1 C7' 1.222(6) . ? N1 C11 1.138(7) . ? N2 C12 1.132(7) . ? C1 C2 1.383(8) . ? C1 C9a 1.385(7) . ? C2 C3 1.364(8) . ? C3 C4 1.392(7) . ? C4 C4a 1.382(6) . ? C4a C9a 1.402(6) . ? C4a C10 1.523(6) . ? C5 C10a 1.390(7) . ? C5 C6 1.392(7) . ? C6 C7 1.375(9) . ? C7 C8 1.377(8) . ? C8 C8a 1.389(7) . ? C8a C10a 1.403(7) . ? C8a C9 1.530(7) . ? C9 C11 1.492(7) . ? C9 C9a 1.537(6) . ? C9 C1' 1.549(6) . ? C10 C12 1.480(6) . ? C10 C10a 1.529(6) . ? C10 C1" 1.603(6) . ? C1' C2' 1.363(7) . ? C1' C7' 1.472(7) . ? C2' C3' 1.435(8) . ? C3' C4' 1.348(10) . ? C4' C5' 1.395(10) . ? C5' C6' 1.354(8) . ? C6' C7' 1.462(7) . ? C1" C2" 1.507(6) . ? C1" C6" 1.545(6) . ? C2" C3" 1.316(7) . ? C3" C4" 1.486(7) . ? C4" C5" 1.519(7) . ? C5" C6" 1.519(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 C2 C1 C9a 121.0(5) . . ? C3 C2 C1 120.2(5) . . ? C2 C3 C4 119.6(5) . . ? C4a C4 C3 121.0(5) . . ? C4 C4a C9a 119.2(4) . . ? C4 C4a C10 121.2(4) . . ? C9a C4a C10 119.6(4) . . ? C10a C5 C6 121.2(5) . . ? C7 C6 C5 118.9(5) . . ? C6 C7 C8 120.6(5) . . ? C7 C8 C8a 121.3(5) . . ? C8 C8a C10a 118.5(5) . . ? C8 C8a C9 120.8(4) . . ? C10a C8a C9 120.7(4) . . ? C11 C9 C8a 108.4(4) . . ? C11 C9 C9a 106.0(4) . . ? C8a C9 C9a 111.5(4) . . ? C11 C9 C1' 109.2(4) . . ? C8a C9 C1' 110.8(4) . . ? C9a C9 C1' 110.8(4) . . ? C1 C9a C4a 119.0(4) . . ? C1 C9a C9 120.5(4) . . ? C4a C9a C9 120.6(4) . . ? C12 C10 C4a 109.5(4) . . ? C12 C10 C10a 109.3(4) . . ? C4a C10 C10a 110.5(4) . . ? C12 C10 C1" 105.4(4) . . ? C4a C10 C1" 111.0(4) . . ? C10a C10 C1" 111.1(3) . . ? C5 C10a C8a 119.3(4) . . ? C5 C10a C10 121.5(4) . . ? C8a C10a C10 119.2(4) . . ? N1 C11 C9 179.0(5) . . ? N2 C12 C10 175.2(5) . . ? C2' C1' C7' 128.1(5) . . ? C2' C1' C9 119.4(4) . . ? C7' C1' C9 112.5(4) . . ? C1' C2' C3' 131.0(6) . . ? C4' C3' C2' 127.7(6) . . ? C3' C4' C5' 128.1(5) . . ? C6' C5' C4' 130.5(6) . . ? C5' C6' C7' 130.3(6) . . ? C5' C6' Br1 116.9(4) . . ? C7' C6' Br1 112.8(4) . . ? O1 C7' C6' 119.7(5) . . ? O1 C7' C1' 118.2(4) . . ? C6' C7' C1' 122.0(5) . . ? C2" C1" C6" 112.1(4) . . ? C2" C1" C10 108.8(4) . . ? C6" C1" C10 111.7(4) . . ? C3" C2" C1" 124.6(5) . . ? C2" C3" C4" 122.8(5) . . ? C3" C4" C5" 109.1(4) . . ? C3" C4" Br2 109.0(4) . . ? C5" C4" Br2 111.2(3) . . ? C6" C5" C4" 110.6(4) . . ? C6" C5" Br3 109.9(3) . . ? C4" C5" Br3 109.5(3) . . ? C5" C6" C1" 114.8(4) . . ? C5" C6" Br4 109.4(3) . . ? C1" C6" Br4 108.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9a C1 C2 C3 1.5(9) . . . . ? C1 C2 C3 C4 -0.4(9) . . . . ? C2 C3 C4 C4a -0.1(8) . . . . ? C3 C4 C4a C9a -0.4(7) . . . . ? C3 C4 C4a C10 179.5(5) . . . . ? C10a C5 C6 C7 2.0(8) . . . . ? C5 C6 C7 C8 -3.3(9) . . . . ? C6 C7 C8 C8a 0.3(10) . . . . ? C7 C8 C8a C10a 3.9(8) . . . . ? C7 C8 C8a C9 -174.9(5) . . . . ? C8 C8a C9 C11 -90.4(5) . . . . ? C10a C8a C9 C11 90.8(5) . . . . ? C8 C8a C9 C9a 153.2(5) . . . . ? C10a C8a C9 C9a -25.5(6) . . . . ? C8 C8a C9 C1' 29.3(6) . . . . ? C10a C8a C9 C1' -149.4(4) . . . . ? C2 C1 C9a C4a -2.0(8) . . . . ? C2 C1 C9a C9 177.3(5) . . . . ? C4 C4a C9a C1 1.4(7) . . . . ? C10 C4a C9a C1 -178.5(4) . . . . ? C4 C4a C9a C9 -177.9(4) . . . . ? C10 C4a C9a C9 2.2(6) . . . . ? C11 C9 C9a C1 91.8(5) . . . . ? C8a C9 C9a C1 -150.4(4) . . . . ? C1' C9 C9a C1 -26.5(6) . . . . ? C11 C9 C9a C4a -88.9(5) . . . . ? C8a C9 C9a C4a 28.9(6) . . . . ? C1' C9 C9a C4a 152.8(4) . . . . ? C4 C4a C10 C12 23.8(6) . . . . ? C9a C4a C10 C12 -156.3(4) . . . . ? C4 C4a C10 C10a 144.2(4) . . . . ? C9a C4a C10 C10a -35.9(6) . . . . ? C4 C4a C10 C1" -92.1(5) . . . . ? C9a C4a C10 C1" 87.8(5) . . . . ? C6 C5 C10a C8a 2.2(7) . . . . ? C6 C5 C10a C10 -175.4(5) . . . . ? C8 C8a C10a C5 -5.1(7) . . . . ? C9 C8a C10a C5 173.7(4) . . . . ? C8 C8a C10a C10 172.6(4) . . . . ? C9 C8a C10a C10 -8.6(6) . . . . ? C12 C10 C10a C5 -22.6(6) . . . . ? C4a C10 C10a C5 -143.1(4) . . . . ? C1" C10 C10a C5 93.2(5) . . . . ? C12 C10 C10a C8a 159.8(4) . . . . ? C4a C10 C10a C8a 39.3(5) . . . . ? C1" C10 C10a C8a -84.4(5) . . . . ? C11 C9 C1' C2' 6.4(6) . . . . ? C8a C9 C1' C2' -113.0(5) . . . . ? C9a C9 C1' C2' 122.8(5) . . . . ? C11 C9 C1' C7' -175.7(4) . . . . ? C8a C9 C1' C7' 65.0(5) . . . . ? C9a C9 C1' C7' -59.3(5) . . . . ? C7' C1' C2' C3' 0.1(10) . . . . ? C9 C1' C2' C3' 177.7(6) . . . . ? C1' C2' C3' C4' 6.6(11) . . . . ? C2' C3' C4' C5' 2.0(11) . . . . ? C3' C4' C5' C6' -7.0(11) . . . . ? C4' C5' C6' C7' -4.8(11) . . . . ? C4' C5' C6' Br1 176.5(5) . . . . ? C5' C6' C7' O1 -166.1(6) . . . . ? Br1 C6' C7' O1 12.7(6) . . . . ? C5' C6' C7' C1' 17.8(8) . . . . ? Br1 C6' C7' C1' -163.5(4) . . . . ? C2' C1' C7' O1 169.3(5) . . . . ? C9 C1' C7' O1 -8.4(7) . . . . ? C2' C1' C7' C6' -14.5(8) . . . . ? C9 C1' C7' C6' 167.8(4) . . . . ? C12 C10 C1" C2" -57.6(5) . . . . ? C4a C10 C1" C2" 60.8(5) . . . . ? C10a C10 C1" C2" -175.8(4) . . . . ? C12 C10 C1" C6" 66.7(4) . . . . ? C4a C10 C1" C6" -174.9(4) . . . . ? C10a C10 C1" C6" -51.5(5) . . . . ? C6" C1" C2" C3" -9.3(7) . . . . ? C10 C1" C2" C3" 114.8(6) . . . . ? C1" C2" C3" C4" 4.1(9) . . . . ? C2" C3" C4" C5" 29.2(7) . . . . ? C2" C3" C4" Br2 150.8(5) . . . . ? C3" C4" C5" C6" -55.7(5) . . . . ? Br2 C4" C5" C6" -175.9(3) . . . . ? C3" C4" C5" Br3 -177.0(3) . . . . ? Br2 C4" C5" Br3 62.8(4) . . . . ? C4" C5" C6" C1" 52.6(5) . . . . ? Br3 C5" C6" C1" 173.7(3) . . . . ? C4" C5" C6" Br4 175.0(3) . . . . ? Br3 C5" C6" Br4 -63.9(4) . . . . ? C2" C1" C6" C5" -19.9(6) . . . . ? C10 C1" C6" C5" -142.3(4) . . . . ? C2" C1" C6" Br4 -142.6(3) . . . . ? C10 C1" C6" Br4 95.0(4) . . . . ?