# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_3,3'-azpy:COOH-I _database_code_depnum_ccdc_archive 'CCDC 906983' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy 1-HB-XB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhCOOH)2 ; _chemical_name_common ;3,3'-AzoPy 1-HB-XB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4- PhCOOH)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H F4 I O2)2 ; _chemical_formula_sum 'C24 H10 F8 I2 N4 O4' _chemical_formula_weight 824.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.9020(3) _cell_length_b 21.4561(12) _cell_length_c 12.1298(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.151(2) _cell_angle_gamma 90.00 _cell_volume 1255.82(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9966 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 32.66 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.606 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4893 _exptl_absorpt_correction_T_max 0.8186 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13823 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 32.56 _reflns_number_total 4126 _reflns_number_gt 3713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0200P)^2^+1.0000P] 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 4126 _refine_ls_number_parameters 236 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0508 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 1.068 _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 N11 N -0.0676(3) 0.01018(7) 0.74150(13) 0.0213(3) Uani 1 1 d . . . H11 H 0.095(5) 0.0424(11) 0.7007(19) 0.026 Uiso 1 1 d . A 1 C12 C -0.1425(4) 0.02582(8) 0.83839(15) 0.0201(3) Uani 1 1 d . . . H12 H -0.0653 0.0621 0.8766 0.024 Uiso 1 1 calc R . . C13 C -0.3301(3) -0.00962(8) 0.88449(15) 0.0193(3) Uani 1 1 d . . . N13 N -0.3986(3) 0.01357(7) 0.98623(13) 0.0207(3) Uani 1 1 d . . . C14 C -0.4335(4) -0.06410(9) 0.83147(16) 0.0233(3) Uani 1 1 d . . . H14 H -0.5590 -0.0896 0.8626 0.028 Uiso 1 1 calc R . . C15 C -0.3497(4) -0.08047(9) 0.73222(17) 0.0264(4) Uani 1 1 d . . . H15 H -0.4147 -0.1178 0.6945 0.032 Uiso 1 1 calc R . . C16 C -0.1699(4) -0.04163(9) 0.68874(16) 0.0252(4) Uani 1 1 d . . . H16 H -0.1176 -0.0521 0.6193 0.030 Uiso 1 1 calc R . . I1 I 1.13019(2) 0.297628(5) 0.463087(9) 0.01950(4) Uani 0.9839(5) 1 d PD . 1 C21A C 0.5658(4) 0.16044(8) 0.65628(15) 0.0168(3) Uani 0.9839(5) 1 d PD . 1 C22A C 0.6296(4) 0.22116(9) 0.69268(17) 0.0180(3) Uani 0.9839(5) 1 d PD . 1 C23A C 0.7966(5) 0.25910(9) 0.64181(17) 0.0174(3) Uani 0.9839(5) 1 d PD . 1 C24A C 0.9061(4) 0.23925(9) 0.55036(15) 0.0173(3) Uani 0.9839(5) 1 d PD . 1 C25A C 0.8456(4) 0.17893(9) 0.51396(15) 0.0187(3) Uani 0.9839(5) 1 d PD . 1 C26A C 0.6807(4) 0.14055(8) 0.56519(15) 0.0181(3) Uani 0.9839(5) 1 d PD . 1 C27A C 0.3839(4) 0.11942(10) 0.71323(17) 0.0175(3) Uani 0.9839(5) 1 d PD . 1 O21A O 0.2475(3) 0.07789(7) 0.64712(12) 0.0242(3) Uani 0.9839(5) 1 d PD . 1 O22A O 0.3710(3) 0.12583(6) 0.81155(11) 0.0247(3) Uani 0.9839(5) 1 d PD . 1 F22A F 0.5178(3) 0.24600(5) 0.77546(11) 0.0235(3) Uani 0.9839(5) 1 d PD . 1 F23A F 0.8437(4) 0.31747(6) 0.68031(11) 0.0240(4) Uani 0.9839(5) 1 d PD . 1 F25A F 0.9486(4) 0.15663(6) 0.42678(12) 0.0265(3) Uani 0.9839(5) 1 d PD . 1 F26A F 0.6419(3) 0.08250(5) 0.52545(11) 0.0238(2) Uani 0.9839(5) 1 d PD . 1 I2 I 0.3175(19) 0.0992(4) 0.6929(8) 0.0175(3) Uani 0.0161(5) 1 d PD . 2 C21B C 0.904(14) 0.2491(18) 0.543(5) 0.0173(3) Uani 0.0161(5) 1 d PD . 2 C22B C 0.869(18) 0.188(2) 0.502(5) 0.0187(3) Uani 0.0161(5) 1 d PD . 2 C23B C 0.747(12) 0.1429(16) 0.557(5) 0.0181(3) Uani 0.0161(5) 1 d PD . 2 C24B C 0.612(13) 0.1578(18) 0.645(5) 0.0168(3) Uani 0.0161(5) 1 d PD . 2 C25B C 0.647(19) 0.218(2) 0.687(6) 0.0180(3) Uani 0.0161(5) 1 d PD . 2 C26B C 0.798(19) 0.261(2) 0.640(6) 0.0174(3) Uani 0.0161(5) 1 d PD . 2 C27B C 1.094(11) 0.2937(16) 0.498(5) 0.01950(4) Uani 0.0161(5) 1 d PD . 2 O21B O 1.013(13) 0.3515(16) 0.499(6) 0.01950(4) Uani 0.0161(5) 1 d PD . 2 O22B O 1.269(11) 0.274(2) 0.447(6) 0.01950(4) Uani 0.0161(5) 1 d PD . 2 F22B F 0.99(2) 0.170(3) 0.417(7) 0.0265(3) Uani 0.0161(5) 1 d PD . 2 F23B F 0.699(19) 0.087(2) 0.507(7) 0.0238(2) Uani 0.0161(5) 1 d PD . 2 F25B F 0.56(2) 0.232(2) 0.782(6) 0.0235(3) Uani 0.0161(5) 1 d PD . 2 F26B F 0.87(3) 0.313(4) 0.700(9) 0.0240(4) Uani 0.0161(5) 1 d PD . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0201(7) 0.0197(7) 0.0250(7) 0.0033(6) 0.0065(6) 0.0003(6) C12 0.0175(7) 0.0179(8) 0.0249(8) 0.0024(6) 0.0040(6) -0.0011(6) C13 0.0177(7) 0.0182(8) 0.0217(7) 0.0037(6) 0.0026(6) -0.0002(6) N13 0.0190(6) 0.0214(7) 0.0218(7) 0.0032(6) 0.0041(5) -0.0009(6) C14 0.0239(8) 0.0196(8) 0.0267(8) 0.0053(7) 0.0053(7) -0.0028(7) C15 0.0316(9) 0.0186(8) 0.0292(9) -0.0002(7) 0.0061(8) -0.0045(8) C16 0.0283(9) 0.0215(8) 0.0271(9) 0.0004(7) 0.0085(7) 0.0024(7) I1 0.01886(6) 0.02132(6) 0.01910(6) 0.00386(4) 0.00548(4) -0.00091(4) C21A 0.0157(7) 0.0185(7) 0.0170(7) 0.0021(6) 0.0050(6) 0.0022(6) C22A 0.0185(8) 0.0204(8) 0.0163(7) -0.0006(6) 0.0068(6) 0.0038(7) C23A 0.0189(7) 0.0142(7) 0.0192(7) -0.0005(6) 0.0038(6) 0.0012(6) C24A 0.0166(7) 0.0183(8) 0.0174(7) 0.0038(6) 0.0044(6) 0.0021(6) C25A 0.0224(8) 0.0202(8) 0.0150(7) -0.0001(6) 0.0074(6) 0.0024(7) C26A 0.0201(8) 0.0174(7) 0.0172(7) -0.0022(6) 0.0045(6) 0.0007(6) C27A 0.0167(8) 0.0144(9) 0.0219(9) 0.0007(7) 0.0052(7) 0.0015(7) O21A 0.0249(6) 0.0257(7) 0.0229(6) -0.0009(6) 0.0066(5) -0.0086(6) O22A 0.0322(7) 0.0225(6) 0.0228(6) 0.0010(5) 0.0144(5) 0.0019(6) F22A 0.0306(7) 0.0197(5) 0.0242(5) -0.0030(5) 0.0158(5) 0.0024(5) F23A 0.0320(8) 0.0159(5) 0.0257(7) -0.0028(5) 0.0096(7) -0.0018(5) F25A 0.0365(8) 0.0252(6) 0.0223(6) -0.0041(5) 0.0179(5) -0.0026(6) F26A 0.0315(7) 0.0189(5) 0.0232(6) -0.0046(4) 0.0112(4) -0.0046(5) I2 0.0167(8) 0.0144(9) 0.0219(9) 0.0007(7) 0.0052(7) 0.0015(7) C21B 0.0166(7) 0.0183(8) 0.0174(7) 0.0038(6) 0.0044(6) 0.0021(6) C22B 0.0224(8) 0.0202(8) 0.0150(7) -0.0001(6) 0.0074(6) 0.0024(7) C23B 0.0201(8) 0.0174(7) 0.0172(7) -0.0022(6) 0.0045(6) 0.0007(6) C24B 0.0157(7) 0.0185(7) 0.0170(7) 0.0021(6) 0.0050(6) 0.0022(6) C25B 0.0185(8) 0.0204(8) 0.0163(7) -0.0006(6) 0.0068(6) 0.0038(7) C26B 0.0189(7) 0.0142(7) 0.0192(7) -0.0005(6) 0.0038(6) 0.0012(6) C27B 0.01886(6) 0.02132(6) 0.01910(6) 0.00386(4) 0.00548(4) -0.00091(4) O21B 0.01886(6) 0.02132(6) 0.01910(6) 0.00386(4) 0.00548(4) -0.00091(4) O22B 0.01886(6) 0.02132(6) 0.01910(6) 0.00386(4) 0.00548(4) -0.00091(4) F22B 0.0365(8) 0.0252(6) 0.0223(6) -0.0041(5) 0.0179(5) -0.0026(6) F23B 0.0315(7) 0.0189(5) 0.0232(6) -0.0046(4) 0.0112(4) -0.0046(5) F25B 0.0306(7) 0.0197(5) 0.0242(5) -0.0030(5) 0.0158(5) 0.0024(5) F26B 0.0320(8) 0.0159(5) 0.0257(7) -0.0028(5) 0.0096(7) -0.0018(5) _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 N11 C12 1.334(2) . ? N11 C16 1.336(2) . ? N11 H11 1.22(2) . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.386(3) . ? C13 N13 1.425(2) . ? N13 N13 1.247(3) 3_457 ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? I1 C24A 2.0751(17) . ? I1 O22A 2.8694(13) 4_665 ? C21A C26A 1.393(2) . ? C21A C22A 1.393(2) . ? C21A C27A 1.505(3) . ? C22A F22A 1.3368(19) . ? C22A C23A 1.375(2) . ? C23A F23A 1.342(2) . ? C23A C24A 1.382(2) . ? C24A C25A 1.383(3) . ? C25A F25A 1.3380(19) . ? C25A C26A 1.376(2) . ? C26A F26A 1.337(2) . ? C27A O22A 1.213(2) . ? C27A O21A 1.302(3) . ? O21A H11 1.32(2) . ? I2 C24B 2.075(5) . ? I2 H11 1.65(3) . ? C21B C26B 1.393(5) . ? C21B C22B 1.394(5) . ? C21B C27B 1.508(6) . ? C22B F22B 1.337(5) . ? C22B C23B 1.375(6) . ? C23B F23B 1.345(6) . ? C23B C24B 1.385(5) . ? C24B C25B 1.382(5) . ? C25B F25B 1.338(5) . ? C25B C26B 1.377(5) . ? C26B F26B 1.338(6) . ? C27B O22B 1.215(6) . ? C27B O21B 1.302(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 C12 N11 C16 119.55(16) . . ? C12 N11 H11 121.0(11) . . ? C16 N11 H11 119.5(11) . . ? N11 C12 C13 121.52(17) . . ? N11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 119.36(17) . . ? C12 C13 N13 115.63(16) . . ? C14 C13 N13 125.01(16) . . ? N13 N13 C13 112.92(19) 3_457 . ? C15 C14 C13 118.50(17) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C16 C15 C14 119.05(18) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N11 C16 C15 121.95(18) . . ? N11 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C24A I1 O22A 170.66(6) . 4_665 ? C26A C21A C22A 116.00(15) . . ? C26A C21A C27A 122.70(17) . . ? C22A C21A C27A 121.31(16) . . ? F22A C22A C23A 117.15(16) . . ? F22A C22A C21A 120.79(15) . . ? C23A C22A C21A 121.97(15) . . ? F23A C23A C22A 118.42(15) . . ? F23A C23A C24A 119.95(15) . . ? C22A C23A C24A 121.59(16) . . ? C23A C24A C25A 116.93(15) . . ? C23A C24A I1 122.61(13) . . ? C25A C24A I1 120.34(12) . . ? F25A C25A C26A 118.44(16) . . ? F25A C25A C24A 119.84(15) . . ? C26A C25A C24A 121.73(15) . . ? F26A C26A C25A 116.88(15) . . ? F26A C26A C21A 121.32(16) . . ? C25A C26A C21A 121.78(16) . . ? O22A C27A O21A 125.0(2) . . ? O22A C27A C21A 121.5(2) . . ? O21A C27A C21A 113.53(16) . . ? C27A O21A H11 111.5(10) . . ? C24B I2 H11 164.6(12) . . ? C26B C21B C22B 116.0(7) . . ? C26B C21B C27B 122.2(9) . . ? C22B C21B C27B 120.6(8) . . ? F22B C22B C23B 116.9(9) . . ? F22B C22B C21B 120.7(9) . . ? C23B C22B C21B 121.8(8) . . ? F23B C23B C22B 118.0(10) . . ? F23B C23B C24B 118.9(9) . . ? C22B C23B C24B 121.0(8) . . ? C25B C24B C23B 117.0(6) . . ? C25B C24B I2 120.4(8) . . ? C23B C24B I2 121.7(8) . . ? F25B C25B C26B 118.2(9) . . ? F25B C25B C24B 119.9(9) . . ? C26B C25B C24B 121.5(7) . . ? F26B C26B C25B 116.7(9) . . ? F26B C26B C21B 121.2(10) . . ? C25B C26B C21B 121.6(6) . . ? O22B C27B O21B 125.0(11) . . ? O22B C27B C21B 120.4(10) . . ? O21B C27B C21B 113.0(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 C16 N11 C12 C13 -1.7(3) . . . . ? N11 C12 C13 C14 2.9(3) . . . . ? N11 C12 C13 N13 -177.94(16) . . . . ? C12 C13 N13 N13 168.34(19) . . . 3_457 ? C14 C13 N13 N13 -12.5(3) . . . 3_457 ? C12 C13 C14 C15 -1.5(3) . . . . ? N13 C13 C14 C15 179.43(17) . . . . ? C13 C14 C15 C16 -1.0(3) . . . . ? C12 N11 C16 C15 -0.9(3) . . . . ? C14 C15 C16 N11 2.2(3) . . . . ? C26A C21A C22A F22A 176.28(19) . . . . ? C27A C21A C22A F22A -3.9(3) . . . . ? C26A C21A C22A C23A -0.1(3) . . . . ? C27A C21A C22A C23A 179.71(19) . . . . ? F22A C22A C23A F23A 2.1(3) . . . . ? C21A C22A C23A F23A 178.6(2) . . . . ? F22A C22A C23A C24A -175.4(2) . . . . ? C21A C22A C23A C24A 1.2(3) . . . . ? F23A C23A C24A C25A -178.95(19) . . . . ? C22A C23A C24A C25A -1.5(3) . . . . ? F23A C23A C24A I1 -2.9(3) . . . . ? C22A C23A C24A I1 174.55(16) . . . . ? O22A I1 C24A C23A -119.8(3) 4_665 . . . ? O22A I1 C24A C25A 56.2(4) 4_665 . . . ? C23A C24A C25A F25A -179.08(19) . . . . ? I1 C24A C25A F25A 4.8(3) . . . . ? C23A C24A C25A C26A 0.9(3) . . . . ? I1 C24A C25A C26A -175.25(15) . . . . ? F25A C25A C26A F26A 1.9(3) . . . . ? C24A C25A C26A F26A -178.08(17) . . . . ? F25A C25A C26A C21A -179.94(18) . . . . ? C24A C25A C26A C21A 0.1(3) . . . . ? C22A C21A C26A F26A 177.61(17) . . . . ? C27A C21A C26A F26A -2.2(3) . . . . ? C22A C21A C26A C25A -0.5(3) . . . . ? C27A C21A C26A C25A 179.69(18) . . . . ? C26A C21A C27A O22A 151.55(19) . . . . ? C22A C21A C27A O22A -28.3(3) . . . . ? C26A C21A C27A O21A -28.4(2) . . . . ? C22A C21A C27A O21A 151.73(18) . . . . ? C26B C21B C22B F22B -173(9) . . . . ? C27B C21B C22B F22B -5(9) . . . . ? C26B C21B C22B C23B -2(8) . . . . ? C27B C21B C22B C23B 166(6) . . . . ? F22B C22B C23B F23B -15(9) . . . . ? C21B C22B C23B F23B 174(7) . . . . ? F22B C22B C23B C24B -178(8) . . . . ? C21B C22B C23B C24B 11(8) . . . . ? F23B C23B C24B C25B -174(6) . . . . ? C22B C23B C24B C25B -11(6) . . . . ? F23B C23B C24B I2 -4(7) . . . . ? C22B C23B C24B I2 159(6) . . . . ? C23B C24B C25B F25B -170(9) . . . . ? I2 C24B C25B F25B 21(9) . . . . ? C23B C24B C25B C26B 3(8) . . . . ? I2 C24B C25B C26B -167(7) . . . . ? F25B C25B C26B F26B 6(12) . . . . ? C24B C25B C26B F26B -167(10) . . . . ? F25B C25B C26B C21B 178(10) . . . . ? C24B C25B C26B C21B 5(10) . . . . ? C22B C21B C26B F26B 166(10) . . . . ? C27B C21B C26B F26B -2(10) . . . . ? C22B C21B C26B C25B -6(8) . . . . ? C27B C21B C26B C25B -173(7) . . . . ? C26B C21B C27B O22B 149(7) . . . . ? C22B C21B C27B O22B -18(8) . . . . ? C26B C21B C27B O21B -44(7) . . . . ? C22B C21B C27B O21B 149(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O21A 1.22(2) 1.32(2) 2.536(2) 174(2) . _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.494 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.086 data_3,3'-azpy:COOH-Br _database_code_depnum_ccdc_archive 'CCDC 906984' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy 2-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhCOOH)2 ; _chemical_name_common ;3,3'-AzoPy 2-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4- PhCOOH)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H Br F4 O2)2 ; _chemical_formula_sum 'C24 H10 Br2 F8 N4 O4' _chemical_formula_weight 730.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.8724(3) _cell_length_b 22.0007(13) _cell_length_c 11.6936(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.336(3) _cell_angle_gamma 90.00 _cell_volume 1229.06(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4953 _cell_measurement_theta_min 4.35 _cell_measurement_theta_max 68.93 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.973 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 5.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5657 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7259 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 69.06 _reflns_number_total 2158 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0350P)^2^+1.0000P] 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 2158 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 N11 N 0.5498(4) 0.48670(9) 0.26066(17) 0.0234(4) Uani 1 1 d . . . C12 C 0.6397(5) 0.47060(10) 0.1642(2) 0.0220(5) Uani 1 1 d . . . H12 H 0.5814 0.4328 0.1282 0.026 Uiso 1 1 calc R . . C13 C 0.8161(5) 0.50772(10) 0.1152(2) 0.0209(5) Uani 1 1 d . . . N13 N 0.9019(4) 0.48508(9) 0.01378(17) 0.0225(4) Uani 1 1 d . . . C14 C 0.8915(5) 0.56446(10) 0.1655(2) 0.0257(5) Uani 1 1 d . . . H14 H 1.0077 0.5912 0.1325 0.031 Uiso 1 1 calc R . . C15 C 0.7935(5) 0.58067(11) 0.2640(2) 0.0274(5) Uani 1 1 d . . . H15 H 0.8397 0.6191 0.2996 0.033 Uiso 1 1 calc R . . C16 C 0.6276(5) 0.54047(11) 0.3103(2) 0.0268(5) Uani 1 1 d . . . H16 H 0.5664 0.5513 0.3798 0.032 Uiso 1 1 calc R . . C21 C -0.0597(5) 0.33440(10) 0.35097(19) 0.0200(5) Uani 1 1 d . . . C27 C 0.1184(5) 0.37530(10) 0.2906(2) 0.0216(5) Uani 1 1 d . . . O21 O 0.2491(4) 0.41703(8) 0.35954(15) 0.0277(4) Uani 1 1 d . . . H21 H 0.380(6) 0.4479(13) 0.312(3) 0.033 Uiso 1 1 d . . . O22 O 0.1307(4) 0.36817(8) 0.18910(14) 0.0287(4) Uani 1 1 d . . . C22 C -0.1119(5) 0.27403(11) 0.31597(19) 0.0215(5) Uani 1 1 d . . . F22 F 0.0079(3) 0.24982(6) 0.23260(12) 0.0272(3) Uani 1 1 d . . . C23 C -0.2723(5) 0.23629(10) 0.36975(19) 0.0210(5) Uani 1 1 d . . . F23 F -0.3083(3) 0.17834(6) 0.33407(12) 0.0277(3) Uani 1 1 d . . . C24 C -0.3897(4) 0.25607(10) 0.46151(18) 0.0197(5) Uani 1 1 d . . . Br1 Br -0.59719(5) 0.204787(10) 0.53986(2) 0.02396(11) Uani 1 1 d . . . C25 C -0.3417(5) 0.31617(11) 0.4969(2) 0.0218(5) Uani 1 1 d . . . F25 F -0.4547(3) 0.33815(6) 0.58394(12) 0.0288(3) Uani 1 1 d . . . C26 C -0.1817(5) 0.35405(10) 0.4424(2) 0.0213(5) Uani 1 1 d . . . F26 F -0.1526(3) 0.41170(6) 0.48094(12) 0.0263(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0241(10) 0.0205(9) 0.0265(10) 0.0046(8) 0.0068(8) 0.0011(8) C12 0.0217(11) 0.0193(11) 0.0242(12) 0.0033(9) 0.0026(9) 0.0015(9) C13 0.0213(11) 0.0198(10) 0.0212(11) 0.0035(9) 0.0035(9) 0.0029(9) N13 0.0225(10) 0.0218(9) 0.0235(9) 0.0035(8) 0.0053(8) 0.0000(7) C14 0.0265(12) 0.0205(11) 0.0307(13) 0.0045(9) 0.0074(10) -0.0023(9) C15 0.0326(13) 0.0193(11) 0.0308(13) -0.0009(9) 0.0074(10) -0.0019(10) C16 0.0319(13) 0.0241(11) 0.0257(12) -0.0001(9) 0.0087(10) 0.0019(10) C21 0.0199(11) 0.0204(11) 0.0195(11) 0.0026(9) 0.0035(9) 0.0025(9) C27 0.0208(11) 0.0210(10) 0.0241(12) 0.0042(9) 0.0070(9) 0.0060(9) O21 0.0303(9) 0.0272(9) 0.0267(9) 0.0016(7) 0.0085(7) -0.0073(7) O22 0.0393(10) 0.0255(9) 0.0256(9) 0.0012(7) 0.0166(7) 0.0020(7) C22 0.0229(11) 0.0232(11) 0.0182(11) -0.0004(9) 0.0034(9) 0.0059(9) F22 0.0341(8) 0.0238(7) 0.0272(7) -0.0029(6) 0.0143(6) 0.0027(6) C23 0.0249(12) 0.0164(10) 0.0207(11) 0.0000(8) 0.0017(9) 0.0014(9) F23 0.0372(8) 0.0171(6) 0.0302(7) -0.0035(5) 0.0099(6) -0.0015(6) C24 0.0203(11) 0.0193(11) 0.0191(11) 0.0043(8) 0.0030(9) -0.0003(8) Br1 0.02494(16) 0.02312(15) 0.02428(16) 0.00543(8) 0.00597(10) -0.00192(9) C25 0.0262(12) 0.0219(11) 0.0182(11) 0.0001(9) 0.0067(9) 0.0036(9) F25 0.0393(8) 0.0263(7) 0.0255(7) -0.0030(6) 0.0179(6) -0.0005(6) C26 0.0231(11) 0.0182(10) 0.0218(11) -0.0015(9) 0.0024(9) 0.0011(9) F26 0.0340(8) 0.0190(7) 0.0280(7) -0.0056(5) 0.0114(6) -0.0031(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.335(3) . ? N11 C16 1.339(3) . ? N11 H21 1.41(3) . ? C12 C13 1.389(3) . ? C12 H12 0.9500 . ? C13 C14 1.398(3) . ? C13 N13 1.422(3) . ? N13 N13 1.253(4) 3_765 ? C14 C15 1.378(4) . ? C14 H14 0.9500 . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.390(3) . ? C21 C22 1.398(3) . ? C21 C27 1.517(3) . ? C27 O22 1.210(3) . ? C27 O21 1.302(3) . ? O21 H21 1.14(3) . ? C22 F22 1.341(3) . ? C22 C23 1.374(3) . ? C23 F23 1.342(3) . ? C23 C24 1.382(3) . ? C24 C25 1.391(3) . ? C24 Br1 1.870(2) . ? Br1 O22 2.8792(17) 4_466 ? C25 F25 1.339(3) . ? C25 C26 1.380(3) . ? C26 F26 1.344(2) . ? 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 C12 N11 C16 119.2(2) . . ? C12 N11 H21 121.4(12) . . ? C16 N11 H21 119.3(12) . . ? N11 C12 C13 121.7(2) . . ? N11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 119.0(2) . . ? C12 C13 N13 116.5(2) . . ? C14 C13 N13 124.6(2) . . ? N13 N13 C13 113.3(2) 3_765 . ? C15 C14 C13 118.5(2) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 119.2(2) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N11 C16 C15 122.3(2) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C26 C21 C22 116.1(2) . . ? C26 C21 C27 122.9(2) . . ? C22 C21 C27 121.0(2) . . ? O22 C27 O21 125.9(2) . . ? O22 C27 C21 121.5(2) . . ? O21 C27 C21 112.64(19) . . ? C27 O21 H21 111.8(15) . . ? F22 C22 C23 117.4(2) . . ? F22 C22 C21 120.7(2) . . ? C23 C22 C21 121.8(2) . . ? F23 C23 C22 118.9(2) . . ? F23 C23 C24 119.5(2) . . ? C22 C23 C24 121.6(2) . . ? C23 C24 C25 117.3(2) . . ? C23 C24 Br1 122.45(17) . . ? C25 C24 Br1 120.21(17) . . ? C24 Br1 O22 172.23(7) . 4_466 ? F25 C25 C26 119.1(2) . . ? F25 C25 C24 119.9(2) . . ? C26 C25 C24 120.9(2) . . ? F26 C26 C25 116.6(2) . . ? F26 C26 C21 121.2(2) . . ? C25 C26 C21 122.2(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 C16 N11 C12 C13 1.2(3) . . . . ? N11 C12 C13 C14 -2.7(3) . . . . ? N11 C12 C13 N13 178.8(2) . . . . ? C12 C13 N13 N13 -167.8(2) . . . 3_765 ? C14 C13 N13 N13 13.8(4) . . . 3_765 ? C12 C13 C14 C15 1.7(3) . . . . ? N13 C13 C14 C15 -179.9(2) . . . . ? C13 C14 C15 C16 0.7(4) . . . . ? C12 N11 C16 C15 1.4(4) . . . . ? C14 C15 C16 N11 -2.3(4) . . . . ? C26 C21 C27 O22 -150.2(2) . . . . ? C22 C21 C27 O22 29.2(3) . . . . ? C26 C21 C27 O21 29.6(3) . . . . ? C22 C21 C27 O21 -150.9(2) . . . . ? C26 C21 C22 F22 -176.6(2) . . . . ? C27 C21 C22 F22 3.9(3) . . . . ? C26 C21 C22 C23 -0.6(3) . . . . ? C27 C21 C22 C23 179.9(2) . . . . ? F22 C22 C23 F23 -2.1(3) . . . . ? C21 C22 C23 F23 -178.23(19) . . . . ? F22 C22 C23 C24 175.9(2) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? F23 C23 C24 C25 178.71(19) . . . . ? C22 C23 C24 C25 0.7(3) . . . . ? F23 C23 C24 Br1 0.5(3) . . . . ? C22 C23 C24 Br1 -177.58(17) . . . . ? C23 C24 Br1 O22 130.3(5) . . . 4_466 ? C25 C24 Br1 O22 -47.9(7) . . . 4_466 ? C23 C24 C25 F25 178.8(2) . . . . ? Br1 C24 C25 F25 -2.9(3) . . . . ? C23 C24 C25 C26 -0.3(3) . . . . ? Br1 C24 C25 C26 177.94(17) . . . . ? F25 C25 C26 F26 -0.6(3) . . . . ? C24 C25 C26 F26 178.51(19) . . . . ? F25 C25 C26 C21 -179.6(2) . . . . ? C24 C25 C26 C21 -0.5(4) . . . . ? C22 C21 C26 F26 -178.00(19) . . . . ? C27 C21 C26 F26 1.5(3) . . . . ? C22 C21 C26 C25 0.9(3) . . . . ? C27 C21 C26 C25 -179.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 N11 1.14(3) 1.41(3) 2.549(2) 177(3) . _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.410 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.074 data_3,3'-azpy:OH-I _database_code_depnum_ccdc_archive 'CCDC 906985' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy-3HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhOH)2 ; _chemical_name_common "3,3'-AzoPy-3HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhOH)2" _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C6 H F4 I O)2 ; _chemical_formula_sum 'C22 H10 F8 I2 N4 O2' _chemical_formula_weight 768.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 19.0228(11) _cell_length_b 16.8636(10) _cell_length_c 7.2425(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.198(2) _cell_angle_gamma 90.00 _cell_volume 2319.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9895 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 32.61 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 2.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4671 _exptl_absorpt_correction_T_max 0.8497 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18196 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 32.02 _reflns_number_total 3957 _reflns_number_gt 3666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0250P)^2^+2.5000P] 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 3957 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0463 _refine_ls_wR_factor_gt 0.0450 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N11 N 0.44861(6) 0.26401(7) 0.55097(17) 0.0216(2) Uani 1 1 d . . . C12 C 0.44090(7) 0.34283(7) 0.5576(2) 0.0195(2) Uani 1 1 d . . . H12 H 0.3979 0.3638 0.5973 0.023 Uiso 1 1 calc R . . C13 C 0.49313(7) 0.39534(8) 0.50890(18) 0.0184(2) Uani 1 1 d . . . N13 N 0.47662(6) 0.47739(7) 0.52716(16) 0.0198(2) Uani 1 1 d . . . C14 C 0.55644(7) 0.36519(9) 0.45002(19) 0.0216(2) Uani 1 1 d . . . H14 H 0.5931 0.3996 0.4159 0.026 Uiso 1 1 calc R . . C15 C 0.56431(7) 0.28374(9) 0.4428(2) 0.0242(3) Uani 1 1 d . . . H15 H 0.6067 0.2611 0.4033 0.029 Uiso 1 1 calc R . . C16 C 0.50959(8) 0.23532(9) 0.4939(2) 0.0243(3) Uani 1 1 d . . . H16 H 0.5156 0.1795 0.4883 0.029 Uiso 1 1 calc R . . C21 C 0.32212(7) 0.12053(7) 0.67850(19) 0.0186(2) Uani 1 1 d . . . O21 O 0.33728(6) 0.19765(6) 0.68085(16) 0.0238(2) Uani 1 1 d . . . H21 H 0.3780(11) 0.2086(12) 0.627(3) 0.029 Uiso 1 1 d . . . C22 C 0.37099(7) 0.05998(8) 0.6571(2) 0.0215(2) Uani 1 1 d . . . F22 F 0.43823(5) 0.07968(6) 0.63190(17) 0.0352(2) Uani 1 1 d . . . C23 C 0.35208(7) -0.01913(8) 0.6614(2) 0.0213(2) Uani 1 1 d . . . F23 F 0.40230(5) -0.07411(5) 0.64176(16) 0.0333(2) Uani 1 1 d . . . C24 C 0.28337(7) -0.04213(7) 0.68760(18) 0.0183(2) Uani 1 1 d . . . I1 I 0.253716(5) -0.160260(5) 0.706907(12) 0.02132(4) Uani 1 1 d . . . C25 C 0.23438(7) 0.01777(8) 0.70671(18) 0.0187(2) Uani 1 1 d . . . F25 F 0.16685(4) -0.00032(5) 0.73284(15) 0.02822(19) Uani 1 1 d . . . C26 C 0.25292(6) 0.09683(8) 0.70167(18) 0.0182(2) Uani 1 1 d . . . F26 F 0.20304(5) 0.15228(5) 0.71769(14) 0.02464(18) 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 N11 0.0200(5) 0.0186(5) 0.0268(5) 0.0010(4) 0.0059(4) -0.0021(4) C12 0.0164(5) 0.0193(6) 0.0232(6) 0.0007(4) 0.0055(4) -0.0015(4) C13 0.0174(5) 0.0180(5) 0.0203(5) 0.0009(4) 0.0048(4) -0.0017(4) N13 0.0177(5) 0.0187(5) 0.0236(5) 0.0010(4) 0.0054(4) -0.0021(4) C14 0.0178(6) 0.0226(6) 0.0250(6) 0.0019(5) 0.0063(5) -0.0012(5) C15 0.0197(6) 0.0240(6) 0.0295(6) 0.0010(5) 0.0088(5) 0.0019(5) C16 0.0238(6) 0.0199(6) 0.0300(6) 0.0014(5) 0.0071(5) 0.0010(5) C21 0.0196(6) 0.0129(5) 0.0238(6) -0.0008(4) 0.0046(4) -0.0013(4) O21 0.0216(5) 0.0125(4) 0.0383(6) -0.0020(4) 0.0094(4) -0.0026(3) C22 0.0148(5) 0.0162(5) 0.0338(7) 0.0013(5) 0.0052(5) -0.0012(4) F22 0.0154(4) 0.0218(4) 0.0695(7) 0.0020(4) 0.0101(4) -0.0016(3) C23 0.0185(6) 0.0148(5) 0.0309(6) -0.0004(5) 0.0050(5) 0.0026(4) F23 0.0213(4) 0.0170(4) 0.0623(6) 0.0008(4) 0.0100(4) 0.0057(3) C24 0.0200(6) 0.0126(5) 0.0226(5) -0.0007(4) 0.0036(4) -0.0010(4) I1 0.02472(5) 0.01213(5) 0.02748(5) -0.00121(3) 0.00473(3) -0.00199(3) C25 0.0163(5) 0.0156(5) 0.0249(6) -0.0004(4) 0.0056(4) -0.0013(4) F25 0.0178(4) 0.0192(4) 0.0487(5) -0.0022(4) 0.0113(4) -0.0026(3) C26 0.0172(6) 0.0143(5) 0.0238(6) -0.0014(4) 0.0056(4) 0.0017(4) F26 0.0197(4) 0.0154(4) 0.0397(5) -0.0018(3) 0.0098(4) 0.0038(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 N11 C12 1.3384(17) . ? N11 C16 1.3430(18) . ? C12 C13 1.3911(18) . ? C12 H12 0.9500 . ? C13 C14 1.3958(18) . ? C13 N13 1.4265(17) . ? N13 N13 1.252(2) 5_666 ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O21 1.3319(16) . ? C21 C26 1.3947(17) . ? C21 C22 1.3954(18) . ? O21 H21 0.90(2) . ? C22 F22 1.3439(15) . ? C22 C23 1.3824(18) . ? C23 F23 1.3446(15) . ? C23 C24 1.3866(18) . ? C24 C25 1.3865(18) . ? C24 I1 2.0772(12) . ? I1 O21 3.0913(10) 4_546 ? C25 F25 1.3440(15) . ? C25 C26 1.3802(18) . ? C26 F26 1.3418(14) . ? 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 C12 N11 C16 117.84(12) . . ? N11 C12 C13 122.81(12) . . ? N11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C12 C13 C14 119.09(12) . . ? C12 C13 N13 115.46(11) . . ? C14 C13 N13 125.44(12) . . ? N13 N13 C13 113.45(14) 5_666 . ? C15 C14 C13 118.06(12) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? C14 C15 C16 119.30(13) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N11 C16 C15 122.90(13) . . ? N11 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? O21 C21 C26 118.90(12) . . ? O21 C21 C22 124.81(12) . . ? C26 C21 C22 116.28(11) . . ? C21 O21 H21 112.6(13) . . ? F22 C22 C23 119.50(12) . . ? F22 C22 C21 118.63(11) . . ? C23 C22 C21 121.86(12) . . ? F23 C23 C22 118.41(12) . . ? F23 C23 C24 120.15(12) . . ? C22 C23 C24 121.43(12) . . ? C25 C24 C23 116.98(12) . . ? C25 C24 I1 120.36(10) . . ? C23 C24 I1 122.62(9) . . ? C24 I1 O21 156.81(4) . 4_546 ? F25 C25 C26 118.08(11) . . ? F25 C25 C24 120.11(11) . . ? C26 C25 C24 121.81(12) . . ? F26 C26 C25 119.20(11) . . ? F26 C26 C21 119.17(11) . . ? C25 C26 C21 121.62(12) . . ? 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 C16 N11 C12 C13 -0.2(2) . . . . ? N11 C12 C13 C14 0.1(2) . . . . ? N11 C12 C13 N13 -178.96(13) . . . . ? C12 C13 N13 N13 -176.45(15) . . . 5_666 ? C14 C13 N13 N13 4.5(2) . . . 5_666 ? C12 C13 C14 C15 0.0(2) . . . . ? N13 C13 C14 C15 179.01(13) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C12 N11 C16 C15 0.2(2) . . . . ? C14 C15 C16 N11 -0.1(2) . . . . ? O21 C21 C22 F22 -1.9(2) . . . . ? C26 C21 C22 F22 179.14(13) . . . . ? O21 C21 C22 C23 178.04(13) . . . . ? C26 C21 C22 C23 -0.9(2) . . . . ? F22 C22 C23 F23 0.6(2) . . . . ? C21 C22 C23 F23 -179.30(13) . . . . ? F22 C22 C23 C24 179.82(13) . . . . ? C21 C22 C23 C24 -0.1(2) . . . . ? F23 C23 C24 C25 -179.96(13) . . . . ? C22 C23 C24 C25 0.8(2) . . . . ? F23 C23 C24 I1 2.05(19) . . . . ? C22 C23 C24 I1 -177.14(11) . . . . ? C25 C24 I1 O21 -21.80(19) . . . 4_546 ? C23 C24 I1 O21 156.12(10) . . . 4_546 ? C23 C24 C25 F25 -179.87(12) . . . . ? I1 C24 C25 F25 -1.84(17) . . . . ? C23 C24 C25 C26 -0.5(2) . . . . ? I1 C24 C25 C26 177.48(10) . . . . ? F25 C25 C26 F26 -1.82(19) . . . . ? C24 C25 C26 F26 178.84(12) . . . . ? F25 C25 C26 C21 178.82(12) . . . . ? C24 C25 C26 C21 -0.5(2) . . . . ? O21 C21 C26 F26 2.83(19) . . . . ? C22 C21 C26 F26 -178.12(12) . . . . ? O21 C21 C26 C25 -177.80(12) . . . . ? C22 C21 C26 C25 1.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 N11 0.90(2) 1.75(2) 2.6162(15) 159(2) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.711 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.090 data_3,3'-azpy:OH-Br _database_code_depnum_ccdc_archive 'CCDC 906986' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy 4-HBXB, (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhOH)2 ; _chemical_name_common ;3,3'-AzoPy 4-HBXB, (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4- PhOH)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C6 H Br F4 O)2 ; _chemical_formula_sum 'C22 H10 Br2 F8 N4 O2' _chemical_formula_weight 674.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.2149(8) _cell_length_b 16.4379(7) _cell_length_c 7.4736(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.631(2) _cell_angle_gamma 90.00 _cell_volume 2206.17(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9456 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 32.48 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.030 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 3.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3602 _exptl_absorpt_correction_T_max 0.4906 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 62309 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 32.03 _reflns_number_total 7628 _reflns_number_gt 6276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0400P)^2^+0.6000P] 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 7628 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.004 _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 N11 N 0.29264(7) 0.32751(7) 0.40896(18) 0.0217(2) Uani 1 1 d . . . C12 C 0.30085(8) 0.40847(8) 0.4039(2) 0.0208(3) Uani 1 1 d . . . H12 H 0.3399 0.4303 0.3488 0.025 Uiso 1 1 calc R . . C13 C 0.25436(8) 0.46153(8) 0.47603(19) 0.0188(3) Uani 1 1 d . . . N13 N 0.27126(7) 0.54567(7) 0.46323(17) 0.0210(2) Uani 1 1 d . . . C14 C 0.19672(8) 0.43036(9) 0.5570(2) 0.0224(3) Uani 1 1 d . . . H14 H 0.1644 0.4654 0.6084 0.027 Uiso 1 1 calc R . . C15 C 0.18814(8) 0.34703(9) 0.5601(2) 0.0243(3) Uani 1 1 d . . . H15 H 0.1492 0.3236 0.6131 0.029 Uiso 1 1 calc R . . C16 C 0.23692(8) 0.29780(9) 0.4853(2) 0.0240(3) Uani 1 1 d . . . H16 H 0.2305 0.2405 0.4884 0.029 Uiso 1 1 calc R . . N21 N 0.19879(7) 0.80875(7) 0.55643(17) 0.0193(2) Uani 1 1 d . . . C22 C 0.18974(8) 0.72821(8) 0.5542(2) 0.0190(3) Uani 1 1 d . . . H22 H 0.1444 0.7065 0.5807 0.023 Uiso 1 1 calc R . . C23 C 0.24367(7) 0.67506(8) 0.51482(18) 0.0171(2) Uani 1 1 d . . . N23 N 0.22599(7) 0.59096(7) 0.52163(17) 0.0202(2) Uani 1 1 d . . . C24 C 0.31036(8) 0.70602(8) 0.4763(2) 0.0190(3) Uani 1 1 d . . . H24 H 0.3485 0.6708 0.4498 0.023 Uiso 1 1 calc R . . C25 C 0.31946(8) 0.78923(9) 0.4776(2) 0.0218(3) Uani 1 1 d . . . H25 H 0.3640 0.8126 0.4505 0.026 Uiso 1 1 calc R . . C26 C 0.26286(8) 0.83857(9) 0.5190(2) 0.0216(3) Uani 1 1 d . . . H26 H 0.2699 0.8958 0.5208 0.026 Uiso 1 1 calc R . . C31 C 0.42327(8) 0.18258(8) 0.29307(19) 0.0187(3) Uani 1 1 d . . . O31 O 0.40806(6) 0.26162(6) 0.29728(17) 0.0259(2) Uani 1 1 d . . . H31 H 0.3664(11) 0.2738(11) 0.336(3) 0.031 Uiso 1 1 d . . . C32 C 0.37931(8) 0.12073(8) 0.3451(2) 0.0191(3) Uani 1 1 d . . . F32 F 0.31726(5) 0.14030(5) 0.41067(14) 0.0281(2) Uani 1 1 d . . . C33 C 0.39780(8) 0.04000(8) 0.3333(2) 0.0195(3) Uani 1 1 d . . . F33 F 0.35257(5) -0.01624(5) 0.38514(13) 0.0286(2) Uani 1 1 d . . . C34 C 0.46230(8) 0.01653(8) 0.27270(18) 0.0186(3) Uani 1 1 d . . . Br1 Br 0.488727(9) -0.092590(8) 0.256845(19) 0.02319(5) Uani 1 1 d . . . C35 C 0.50769(8) 0.07742(9) 0.22634(19) 0.0190(3) Uani 1 1 d . . . F35 F 0.57247(5) 0.05899(5) 0.17431(13) 0.02653(19) Uani 1 1 d . . . C36 C 0.48812(8) 0.15833(8) 0.2341(2) 0.0194(3) Uani 1 1 d . . . F36 F 0.53358(5) 0.21526(5) 0.18432(14) 0.0271(2) Uani 1 1 d . . . C41 C 0.07159(7) 0.95252(8) 0.68450(18) 0.0165(2) Uani 1 1 d . . . O41 O 0.08600(6) 0.87391(6) 0.67382(15) 0.0213(2) Uani 1 1 d . . . H41 H 0.1271(11) 0.8593(11) 0.634(2) 0.026 Uiso 1 1 d . . . C42 C 0.11284(8) 1.01521(8) 0.62546(19) 0.0185(3) Uani 1 1 d . . . F42 F 0.17296(5) 0.99637(5) 0.55136(14) 0.0293(2) Uani 1 1 d . . . C43 C 0.09391(8) 1.09586(8) 0.6395(2) 0.0190(3) Uani 1 1 d . . . F43 F 0.13703(5) 1.15257(5) 0.58130(14) 0.0285(2) Uani 1 1 d . . . C44 C 0.03237(8) 1.11862(8) 0.71328(18) 0.0174(2) Uani 1 1 d . . . Br2 Br 0.006115(8) 1.226936(8) 0.738025(19) 0.02132(4) Uani 1 1 d . . . C45 C -0.00975(7) 1.05678(8) 0.77033(19) 0.0189(3) Uani 1 1 d . . . F45 F -0.07127(5) 1.07446(5) 0.83880(14) 0.0281(2) Uani 1 1 d . . . C46 C 0.00916(8) 0.97663(8) 0.75673(18) 0.0180(3) Uani 1 1 d . . . F46 F -0.03455(5) 0.91892(5) 0.81072(14) 0.0268(2) 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 N11 0.0203(6) 0.0142(5) 0.0320(7) -0.0009(5) 0.0084(5) 0.0012(4) C12 0.0196(6) 0.0152(6) 0.0293(7) -0.0007(5) 0.0089(6) 0.0010(5) C13 0.0175(6) 0.0125(6) 0.0272(7) 0.0000(5) 0.0064(5) 0.0013(4) N13 0.0205(6) 0.0138(5) 0.0302(6) -0.0010(5) 0.0086(5) 0.0011(4) C14 0.0199(7) 0.0154(6) 0.0334(8) -0.0003(5) 0.0089(6) 0.0017(5) C15 0.0211(7) 0.0176(7) 0.0366(8) 0.0025(6) 0.0121(6) 0.0003(5) C16 0.0226(7) 0.0154(6) 0.0353(8) 0.0001(5) 0.0082(6) -0.0014(5) N21 0.0201(6) 0.0134(5) 0.0261(6) 0.0003(4) 0.0085(5) 0.0015(4) C22 0.0180(6) 0.0146(6) 0.0261(7) 0.0007(5) 0.0082(5) 0.0001(5) C23 0.0174(6) 0.0133(6) 0.0214(6) -0.0004(5) 0.0061(5) 0.0009(4) N23 0.0188(6) 0.0132(5) 0.0297(6) 0.0000(4) 0.0077(5) 0.0019(4) C24 0.0174(6) 0.0162(6) 0.0248(7) -0.0006(5) 0.0071(5) 0.0015(5) C25 0.0184(6) 0.0181(6) 0.0308(8) -0.0005(5) 0.0100(6) -0.0020(5) C26 0.0234(7) 0.0141(6) 0.0292(8) -0.0003(5) 0.0099(6) -0.0017(5) C31 0.0198(6) 0.0117(6) 0.0250(7) 0.0001(5) 0.0048(5) 0.0002(5) O31 0.0232(5) 0.0116(4) 0.0455(7) 0.0002(4) 0.0135(5) 0.0011(4) C32 0.0161(6) 0.0151(6) 0.0270(7) 0.0003(5) 0.0059(5) 0.0006(5) F32 0.0208(4) 0.0191(4) 0.0478(6) 0.0009(4) 0.0158(4) 0.0007(3) C33 0.0213(6) 0.0128(6) 0.0244(7) 0.0017(5) 0.0032(5) -0.0028(5) F33 0.0281(5) 0.0154(4) 0.0447(6) 0.0041(4) 0.0126(4) -0.0050(3) C34 0.0239(7) 0.0122(6) 0.0195(6) -0.0002(5) 0.0027(5) 0.0016(5) Br1 0.03338(9) 0.01191(7) 0.02374(8) -0.00094(5) 0.00316(6) 0.00412(5) C35 0.0203(6) 0.0165(6) 0.0213(7) 0.0010(5) 0.0068(5) 0.0031(5) F35 0.0259(4) 0.0213(4) 0.0358(5) 0.0023(4) 0.0151(4) 0.0059(3) C36 0.0202(6) 0.0127(6) 0.0265(7) 0.0019(5) 0.0074(5) -0.0010(5) F36 0.0250(4) 0.0154(4) 0.0446(6) 0.0036(4) 0.0167(4) -0.0023(3) C41 0.0182(6) 0.0114(5) 0.0204(6) -0.0006(5) 0.0045(5) 0.0003(4) O41 0.0217(5) 0.0104(4) 0.0343(6) -0.0006(4) 0.0122(4) 0.0011(4) C42 0.0180(6) 0.0139(6) 0.0256(7) -0.0019(5) 0.0093(5) 0.0004(5) F42 0.0267(5) 0.0177(4) 0.0494(6) -0.0008(4) 0.0239(4) 0.0014(3) C43 0.0220(7) 0.0114(6) 0.0248(7) 0.0010(5) 0.0079(5) -0.0033(5) F43 0.0299(5) 0.0136(4) 0.0466(6) 0.0012(4) 0.0200(4) -0.0040(3) C44 0.0209(6) 0.0109(5) 0.0206(6) -0.0014(5) 0.0044(5) 0.0005(5) Br2 0.02916(8) 0.01104(7) 0.02484(8) -0.00158(5) 0.00766(6) 0.00258(5) C45 0.0206(6) 0.0138(6) 0.0239(7) -0.0014(5) 0.0087(5) 0.0012(5) F45 0.0265(5) 0.0185(4) 0.0447(6) 0.0011(4) 0.0217(4) 0.0041(3) C46 0.0192(6) 0.0126(6) 0.0235(7) 0.0014(5) 0.0071(5) -0.0016(5) F46 0.0266(5) 0.0140(4) 0.0443(6) 0.0026(4) 0.0193(4) -0.0019(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 N11 C16 1.3369(19) . ? N11 C12 1.3405(17) . ? C12 C13 1.3862(19) . ? C12 H12 0.9500 . ? C13 C14 1.394(2) . ? C13 N13 1.4236(17) . ? N13 N23 1.2430(17) . ? C14 C15 1.3792(19) . ? C14 H14 0.9500 . ? C15 C16 1.387(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C22 1.3338(17) . ? N21 C26 1.3379(18) . ? C22 C23 1.3827(18) . ? C22 H22 0.9500 . ? C23 C24 1.3908(19) . ? C23 N23 1.4223(17) . ? C24 C25 1.3776(18) . ? C24 H24 0.9500 . ? C25 C26 1.387(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 O31 1.3299(16) . ? C31 C36 1.3865(19) . ? C31 C32 1.3894(18) . ? O31 H31 0.88(2) . ? C32 F32 1.3440(16) . ? C32 C33 1.3756(18) . ? C33 F33 1.3380(15) . ? C33 C34 1.383(2) . ? C34 C35 1.3788(19) . ? C34 Br1 1.8661(13) . ? Br1 O31 3.1138(11) 2_645 ? C35 F35 1.3376(16) . ? C35 C36 1.3806(19) . ? C36 F36 1.3429(15) . ? C41 O41 1.3236(15) . ? C41 C42 1.3899(18) . ? C41 C46 1.3954(19) . ? O41 H41 0.88(2) . ? C42 F42 1.3434(15) . ? C42 C43 1.3782(18) . ? C43 F43 1.3376(15) . ? C43 C44 1.381(2) . ? C44 C45 1.3831(19) . ? C44 Br2 1.8609(13) . ? Br2 O41 3.0750(10) 2_556 ? C45 F45 1.3395(15) . ? C45 C46 1.3698(19) . ? C46 F46 1.3432(15) . ? 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 C16 N11 C12 118.10(13) . . ? N11 C12 C13 122.36(13) . . ? N11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C12 C13 C14 119.41(13) . . ? C12 C13 N13 115.60(12) . . ? C14 C13 N13 124.97(12) . . ? N23 N13 C13 113.25(12) . . ? C15 C14 C13 117.91(13) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? C14 C15 C16 119.38(14) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N11 C16 C15 122.83(13) . . ? N11 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C22 N21 C26 118.12(12) . . ? N21 C22 C23 122.62(13) . . ? N21 C22 H22 118.7 . . ? C23 C22 H22 118.7 . . ? C22 C23 C24 119.29(12) . . ? C22 C23 N23 115.68(12) . . ? C24 C23 N23 125.02(12) . . ? N13 N23 C23 113.71(12) . . ? C25 C24 C23 118.03(13) . . ? C25 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? C24 C25 C26 119.30(13) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? N21 C26 C25 122.65(13) . . ? N21 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? O31 C31 C36 118.70(12) . . ? O31 C31 C32 125.18(13) . . ? C36 C31 C32 116.11(12) . . ? C31 O31 H31 115.1(12) . . ? F32 C32 C33 118.97(12) . . ? F32 C32 C31 119.08(12) . . ? C33 C32 C31 121.95(13) . . ? F33 C33 C32 118.59(13) . . ? F33 C33 C34 120.02(12) . . ? C32 C33 C34 121.38(12) . . ? C35 C34 C33 117.25(12) . . ? C35 C34 Br1 120.66(11) . . ? C33 C34 Br1 122.09(10) . . ? C34 Br1 O31 156.32(5) . 2_645 ? F35 C35 C34 120.25(13) . . ? F35 C35 C36 118.49(12) . . ? C34 C35 C36 121.25(13) . . ? F36 C36 C35 118.95(12) . . ? F36 C36 C31 119.04(12) . . ? C35 C36 C31 122.01(12) . . ? O41 C41 C42 125.56(12) . . ? O41 C41 C46 118.89(12) . . ? C42 C41 C46 115.53(12) . . ? C41 O41 H41 118.2(12) . . ? F42 C42 C43 118.99(12) . . ? F42 C42 C41 118.76(11) . . ? C43 C42 C41 122.25(12) . . ? F43 C43 C42 118.52(12) . . ? F43 C43 C44 120.07(12) . . ? C42 C43 C44 121.40(12) . . ? C43 C44 C45 116.94(12) . . ? C43 C44 Br2 122.55(10) . . ? C45 C44 Br2 120.50(10) . . ? C44 Br2 O41 158.68(5) . 2_556 ? F45 C45 C46 118.29(12) . . ? F45 C45 C44 120.06(12) . . ? C46 C45 C44 121.65(13) . . ? F46 C46 C45 119.21(12) . . ? F46 C46 C41 118.56(12) . . ? C45 C46 C41 122.22(12) . . ? 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 C16 N11 C12 C13 0.6(2) . . . . ? N11 C12 C13 C14 -0.1(2) . . . . ? N11 C12 C13 N13 178.77(13) . . . . ? C12 C13 N13 N23 176.70(13) . . . . ? C14 C13 N13 N23 -4.5(2) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? N13 C13 C14 C15 -179.30(14) . . . . ? C13 C14 C15 C16 0.6(2) . . . . ? C12 N11 C16 C15 -0.6(2) . . . . ? C14 C15 C16 N11 -0.1(2) . . . . ? C26 N21 C22 C23 -0.1(2) . . . . ? N21 C22 C23 C24 0.2(2) . . . . ? N21 C22 C23 N23 178.80(13) . . . . ? C13 N13 N23 C23 178.11(11) . . . . ? C22 C23 N23 N13 171.28(13) . . . . ? C24 C23 N23 N13 -10.2(2) . . . . ? C22 C23 C24 C25 -0.5(2) . . . . ? N23 C23 C24 C25 -179.00(13) . . . . ? C23 C24 C25 C26 0.8(2) . . . . ? C22 N21 C26 C25 0.3(2) . . . . ? C24 C25 C26 N21 -0.7(2) . . . . ? O31 C31 C32 F32 -2.1(2) . . . . ? C36 C31 C32 F32 177.29(13) . . . . ? O31 C31 C32 C33 178.53(14) . . . . ? C36 C31 C32 C33 -2.1(2) . . . . ? F32 C32 C33 F33 1.0(2) . . . . ? C31 C32 C33 F33 -179.69(13) . . . . ? F32 C32 C33 C34 -177.78(13) . . . . ? C31 C32 C33 C34 1.6(2) . . . . ? F33 C33 C34 C35 -178.11(12) . . . . ? C32 C33 C34 C35 0.6(2) . . . . ? F33 C33 C34 Br1 0.91(19) . . . . ? C32 C33 C34 Br1 179.64(11) . . . . ? C35 C34 Br1 O31 8.9(2) . . . 2_645 ? C33 C34 Br1 O31 -170.14(9) . . . 2_645 ? C33 C34 C35 F35 177.08(13) . . . . ? Br1 C34 C35 F35 -1.96(18) . . . . ? C33 C34 C35 C36 -2.2(2) . . . . ? Br1 C34 C35 C36 178.75(11) . . . . ? F35 C35 C36 F36 1.9(2) . . . . ? C34 C35 C36 F36 -178.77(13) . . . . ? F35 C35 C36 C31 -177.58(13) . . . . ? C34 C35 C36 C31 1.7(2) . . . . ? O31 C31 C36 F36 0.4(2) . . . . ? C32 C31 C36 F36 -179.07(13) . . . . ? O31 C31 C36 C35 179.89(13) . . . . ? C32 C31 C36 C35 0.4(2) . . . . ? O41 C41 C42 F42 -0.3(2) . . . . ? C46 C41 C42 F42 -178.82(13) . . . . ? O41 C41 C42 C43 179.34(14) . . . . ? C46 C41 C42 C43 0.8(2) . . . . ? F42 C42 C43 F43 -1.1(2) . . . . ? C41 C42 C43 F43 179.27(13) . . . . ? F42 C42 C43 C44 179.50(13) . . . . ? C41 C42 C43 C44 -0.2(2) . . . . ? F43 C43 C44 C45 179.88(13) . . . . ? C42 C43 C44 C45 -0.7(2) . . . . ? F43 C43 C44 Br2 -0.5(2) . . . . ? C42 C43 C44 Br2 178.92(11) . . . . ? C43 C44 Br2 O41 175.39(9) . . . 2_556 ? C45 C44 Br2 O41 -5.0(2) . . . 2_556 ? C43 C44 C45 F45 -178.27(13) . . . . ? Br2 C44 C45 F45 2.11(19) . . . . ? C43 C44 C45 C46 0.9(2) . . . . ? Br2 C44 C45 C46 -178.77(11) . . . . ? F45 C45 C46 F46 0.5(2) . . . . ? C44 C45 C46 F46 -178.63(13) . . . . ? F45 C45 C46 C41 178.98(13) . . . . ? C44 C45 C46 C41 -0.2(2) . . . . ? O41 C41 C46 F46 -0.8(2) . . . . ? C42 C41 C46 F46 177.80(12) . . . . ? O41 C41 C46 C45 -179.29(13) . . . . ? C42 C41 C46 C45 -0.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 0.88(2) 1.77(2) 2.6224(16) 163.2(18) . O41 H41 N21 0.88(2) 1.73(2) 2.5963(15) 166.8(18) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.409 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.123 data_3,3'-azpy:Ox-I _database_code_depnum_ccdc_archive 'CCDC 906987' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy 8-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhCH=NOH)2 ; _chemical_name_common ;3,3'-AzoPy 8-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4- PhCH=NOH)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H2 F4 I N O)2 ; _chemical_formula_sum 'C24 H12 F8 I2 N6 O2' _chemical_formula_weight 822.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 5.6341(4) _cell_length_b 10.4834(7) _cell_length_c 11.5197(8) _cell_angle_alpha 75.365(2) _cell_angle_beta 77.562(2) _cell_angle_gamma 80.975(2) _cell_volume 639.09(8) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 33.12 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 2.556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4951 _exptl_absorpt_correction_T_max 0.7161 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15760 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 33.15 _reflns_number_total 4637 _reflns_number_gt 4497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0200P)^2^+0.3000P] 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 4637 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0194 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0444 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N -0.0478(2) 0.10679(12) 0.66176(11) 0.0209(2) Uani 1 1 d . . . C12 C 0.0013(3) 0.08253(14) 0.77374(13) 0.0192(2) Uani 1 1 d . . . H12 H 0.1308 0.1226 0.7863 0.023 Uiso 1 1 calc R . . C13 C -0.1310(3) 0.00008(13) 0.87338(12) 0.0176(2) Uani 1 1 d . . . N13 N -0.0771(2) -0.03272(12) 0.99305(11) 0.0198(2) Uani 1 1 d . . . C14 C -0.3214(3) -0.05736(14) 0.85597(13) 0.0198(2) Uani 1 1 d . . . H14 H -0.4153 -0.1130 0.9224 0.024 Uiso 1 1 calc R . . C15 C -0.3720(3) -0.03193(15) 0.73944(14) 0.0222(3) Uani 1 1 d . . . H15 H -0.5015 -0.0698 0.7241 0.027 Uiso 1 1 calc R . . C16 C -0.2304(3) 0.04964(15) 0.64576(14) 0.0221(3) Uani 1 1 d . . . H16 H -0.2648 0.0659 0.5658 0.026 Uiso 1 1 calc R . . I1 I 0.262421(15) 0.276903(8) 0.484817(7) 0.01735(3) Uani 1 1 d . . . C21 C 0.8719(2) 0.53586(13) 0.18053(12) 0.0164(2) Uani 1 1 d . . . C22 C 0.9113(2) 0.39903(13) 0.22241(12) 0.0167(2) Uani 1 1 d . . . F22 F 1.11968(16) 0.33137(9) 0.17910(9) 0.02428(18) Uani 1 1 d . . . C23 C 0.7401(2) 0.32804(13) 0.30664(12) 0.0167(2) Uani 1 1 d . . . F23 F 0.79272(16) 0.19614(8) 0.34014(8) 0.02239(17) Uani 1 1 d . . . C24 C 0.5177(2) 0.38851(13) 0.35592(12) 0.0170(2) Uani 1 1 d . . . C25 C 0.4747(3) 0.52427(14) 0.31391(13) 0.0192(2) Uani 1 1 d . . . F25 F 0.26300(17) 0.58962(10) 0.35554(10) 0.0290(2) Uani 1 1 d . . . C26 C 0.6457(3) 0.59544(13) 0.22896(13) 0.0178(2) Uani 1 1 d . . . F26 F 0.59088(17) 0.72645(9) 0.19158(9) 0.02510(19) Uani 1 1 d . . . C27 C 1.0464(3) 0.61726(13) 0.09188(13) 0.0184(2) Uani 1 1 d . . . H27A H 1.0022 0.7097 0.0653 0.022 Uiso 1 1 calc R . . N27 N 1.2581(2) 0.56562(12) 0.04960(11) 0.0191(2) Uani 1 1 d . . . O27 O 1.3951(2) 0.66080(11) -0.03321(10) 0.0237(2) Uani 1 1 d . . . H27 H 1.505(4) 0.621(2) -0.054(2) 0.028 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0204(5) 0.0201(5) 0.0188(5) -0.0013(4) 0.0000(4) -0.0021(4) C12 0.0190(6) 0.0179(6) 0.0186(6) -0.0020(4) -0.0002(5) -0.0042(5) C13 0.0186(6) 0.0153(5) 0.0175(5) -0.0028(4) -0.0002(5) -0.0033(4) N13 0.0218(6) 0.0178(5) 0.0186(5) -0.0017(4) -0.0010(4) -0.0064(4) C14 0.0185(6) 0.0168(6) 0.0226(6) -0.0039(5) 0.0002(5) -0.0037(4) C15 0.0188(6) 0.0221(6) 0.0262(7) -0.0071(5) -0.0030(5) -0.0023(5) C16 0.0211(6) 0.0231(6) 0.0210(6) -0.0042(5) -0.0049(5) 0.0008(5) I1 0.01457(4) 0.01967(5) 0.01558(4) -0.00206(3) 0.00098(3) -0.00362(3) C21 0.0154(5) 0.0158(5) 0.0168(5) -0.0025(4) -0.0006(4) -0.0034(4) C22 0.0135(5) 0.0166(5) 0.0175(5) -0.0033(4) 0.0011(4) -0.0005(4) F22 0.0169(4) 0.0177(4) 0.0296(4) -0.0014(3) 0.0072(3) 0.0011(3) C23 0.0168(6) 0.0136(5) 0.0177(5) -0.0014(4) -0.0010(4) -0.0019(4) F23 0.0200(4) 0.0136(3) 0.0272(4) 0.0012(3) 0.0021(3) -0.0013(3) C24 0.0150(5) 0.0179(6) 0.0168(5) -0.0037(4) 0.0005(4) -0.0027(4) C25 0.0144(5) 0.0186(6) 0.0226(6) -0.0060(5) 0.0013(5) -0.0005(4) F25 0.0181(4) 0.0220(4) 0.0390(5) -0.0063(4) 0.0083(4) 0.0019(3) C26 0.0177(6) 0.0133(5) 0.0208(6) -0.0031(4) -0.0016(5) -0.0009(4) F26 0.0229(4) 0.0135(4) 0.0334(5) -0.0024(3) 0.0020(4) -0.0002(3) C27 0.0183(6) 0.0159(5) 0.0196(6) -0.0025(4) -0.0003(5) -0.0042(4) N27 0.0179(5) 0.0183(5) 0.0191(5) -0.0015(4) 0.0012(4) -0.0070(4) O27 0.0192(5) 0.0209(5) 0.0258(5) -0.0011(4) 0.0058(4) -0.0073(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 N11 C12 1.3310(19) . ? N11 C16 1.335(2) . ? N11 I1 2.8279(12) . ? C12 C13 1.3973(18) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 N13 1.4208(19) . ? N13 N13 1.247(2) 2_557 ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 C16 1.382(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? I1 C24 2.0910(13) . ? C21 C22 1.3915(18) . ? C21 C26 1.3946(18) . ? C21 C27 1.4590(18) . ? C22 F22 1.3400(15) . ? C22 C23 1.3722(18) . ? C23 F23 1.3416(15) . ? C23 C24 1.3859(18) . ? C24 C25 1.3830(19) . ? C25 F25 1.3362(15) . ? C25 C26 1.3759(19) . ? C26 F26 1.3388(15) . ? C27 N27 1.2782(18) . ? C27 H27A 0.9500 . ? N27 O27 1.3944(15) . ? O27 H27 0.72(2) . ? 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 C12 N11 C16 118.05(12) . . ? C12 N11 I1 113.73(9) . . ? C16 N11 I1 128.22(10) . . ? N11 C12 C13 122.24(13) . . ? N11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C14 C13 C12 119.20(13) . . ? C14 C13 N13 116.94(12) . . ? C12 C13 N13 123.84(13) . . ? N13 N13 C13 114.26(15) 2_557 . ? C13 C14 C15 118.41(13) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 118.66(14) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N11 C16 C15 123.43(14) . . ? N11 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C24 I1 N11 174.75(4) . . ? C22 C21 C26 115.43(12) . . ? C22 C21 C27 124.93(12) . . ? C26 C21 C27 119.64(12) . . ? F22 C22 C23 117.51(12) . . ? F22 C22 C21 120.32(11) . . ? C23 C22 C21 122.15(12) . . ? F23 C23 C22 117.93(12) . . ? F23 C23 C24 120.09(12) . . ? C22 C23 C24 121.97(12) . . ? C25 C24 C23 116.48(12) . . ? C25 C24 I1 122.71(10) . . ? C23 C24 I1 120.80(10) . . ? F25 C25 C26 118.29(12) . . ? F25 C25 C24 120.13(12) . . ? C26 C25 C24 121.58(12) . . ? F26 C26 C25 118.36(12) . . ? F26 C26 C21 119.28(12) . . ? C25 C26 C21 122.37(12) . . ? N27 C27 C21 120.76(12) . . ? N27 C27 H27A 119.6 . . ? C21 C27 H27A 119.6 . . ? C27 N27 O27 111.31(12) . . ? N27 O27 H27 101.9(19) . . ? 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 C16 N11 C12 C13 0.0(2) . . . . ? I1 N11 C12 C13 -179.59(10) . . . . ? N11 C12 C13 C14 -0.8(2) . . . . ? N11 C12 C13 N13 177.15(13) . . . . ? C14 C13 N13 N13 -172.40(16) . . . 2_557 ? C12 C13 N13 N13 9.6(2) . . . 2_557 ? C12 C13 C14 C15 0.7(2) . . . . ? N13 C13 C14 C15 -177.32(13) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C12 N11 C16 C15 0.7(2) . . . . ? I1 N11 C16 C15 -179.72(10) . . . . ? C14 C15 C16 N11 -0.7(2) . . . . ? C26 C21 C22 F22 178.06(13) . . . . ? C27 C21 C22 F22 -1.7(2) . . . . ? C26 C21 C22 C23 -0.7(2) . . . . ? C27 C21 C22 C23 179.59(14) . . . . ? F22 C22 C23 F23 0.1(2) . . . . ? C21 C22 C23 F23 178.94(13) . . . . ? F22 C22 C23 C24 -179.27(13) . . . . ? C21 C22 C23 C24 -0.5(2) . . . . ? F23 C23 C24 C25 -178.13(13) . . . . ? C22 C23 C24 C25 1.3(2) . . . . ? F23 C23 C24 I1 0.94(18) . . . . ? C22 C23 C24 I1 -179.66(11) . . . . ? C23 C24 C25 F25 178.96(13) . . . . ? I1 C24 C25 F25 -0.1(2) . . . . ? C23 C24 C25 C26 -0.9(2) . . . . ? I1 C24 C25 C26 -179.95(11) . . . . ? F25 C25 C26 F26 -0.5(2) . . . . ? C24 C25 C26 F26 179.41(13) . . . . ? F25 C25 C26 C21 179.86(13) . . . . ? C24 C25 C26 C21 -0.3(2) . . . . ? C22 C21 C26 F26 -178.61(13) . . . . ? C27 C21 C26 F26 1.1(2) . . . . ? C22 C21 C26 C25 1.1(2) . . . . ? C27 C21 C26 C25 -179.20(14) . . . . ? C22 C21 C27 N27 -2.9(2) . . . . ? C26 C21 C27 N27 177.43(14) . . . . ? C21 C27 N27 O27 -179.84(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O27 H27 N27 0.72(2) 2.18(2) 2.8460(17) 153(2) 2_865 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.572 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.095 data_3,3'-azpy:Ox-Br _database_code_depnum_ccdc_archive 'CCDC 906988' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy 5-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhCHO oxime)2 ; _chemical_name_common ;3,3'-AzoPy 5-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhCHO oxime)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H2 Br F4 N O)2 ; _chemical_formula_sum 'C24 H12 Br2 F8 N6 O2' _chemical_formula_weight 728.22 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' 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' F F 0.0171 0.0103 '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' _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 8.3500(8) _cell_length_b 8.3646(8) _cell_length_c 9.8996(10) _cell_angle_alpha 105.765(3) _cell_angle_beta 103.151(3) _cell_angle_gamma 99.733(3) _cell_volume 628.00(11) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5691 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 31.29 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.926 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 3.325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4159 _exptl_absorpt_correction_T_max 0.8255 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10635 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 31.49 _reflns_number_total 3773 _reflns_number_gt 3174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0900P)^2^+0.0500P] 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 3773 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.69484(3) 1.09011(3) 0.90003(3) 0.02597(12) Uani 1 1 d . . . C11 C 0.6696(3) 0.6372(3) 0.4834(3) 0.0187(5) Uani 1 1 d . . . C12 C 0.5453(3) 0.7296(3) 0.4859(3) 0.0200(5) Uani 1 1 d . . . F12 F 0.4097(2) 0.6899(2) 0.36964(18) 0.0280(4) Uani 1 1 d . . . C13 C 0.5542(3) 0.8624(3) 0.6080(3) 0.0216(5) Uani 1 1 d . . . F13 F 0.4273(2) 0.9416(2) 0.60229(18) 0.0284(4) Uani 1 1 d . . . C14 C 0.6875(3) 0.9127(3) 0.7349(3) 0.0203(5) Uani 1 1 d . . . C15 C 0.8119(3) 0.8207(3) 0.7362(3) 0.0224(5) Uani 1 1 d . . . F15 F 0.9424(2) 0.8600(2) 0.85587(18) 0.0293(4) Uani 1 1 d . . . C16 C 0.8022(3) 0.6887(3) 0.6135(3) 0.0207(5) Uani 1 1 d . . . F16 F 0.9270(2) 0.6049(2) 0.62079(19) 0.0293(4) Uani 1 1 d . . . C17 C 0.6678(3) 0.4923(3) 0.3602(3) 0.0221(5) Uani 1 1 d . . . H17A H 0.7564 0.4346 0.3694 0.026 Uiso 1 1 calc R . . N17 N 0.5480(3) 0.4427(3) 0.2403(3) 0.0231(4) Uani 1 1 d . . . O17 O 0.5707(3) 0.3020(3) 0.1405(2) 0.0269(4) Uani 1 1 d . . . H17 H 0.492(5) 0.288(5) 0.079(4) 0.032 Uiso 1 1 d . . . N21 N 0.2842(3) 0.2591(3) -0.0736(3) 0.0265(5) Uani 1 1 d . . . C22 C 0.2229(3) 0.1320(4) -0.2009(3) 0.0250(5) Uani 1 1 d . . . H22 H 0.2720 0.0365 -0.2143 0.030 Uiso 1 1 calc R . . C23 C 0.0910(3) 0.1324(4) -0.3147(3) 0.0227(5) Uani 1 1 d . . . N23 N 0.0465(3) -0.0109(3) -0.4453(3) 0.0240(5) Uani 1 1 d . . . C24 C 0.0128(4) 0.2682(4) -0.2939(3) 0.0255(5) Uani 1 1 d . . . H24 H -0.0795 0.2713 -0.3689 0.031 Uiso 1 1 calc R . . C25 C 0.0736(4) 0.3980(4) -0.1609(3) 0.0278(6) Uani 1 1 d . . . H25 H 0.0225 0.4918 -0.1425 0.033 Uiso 1 1 calc R . . C26 C 0.2095(4) 0.3907(4) -0.0544(3) 0.0269(5) Uani 1 1 d . . . H26 H 0.2517 0.4823 0.0358 0.032 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 Br1 0.02809(16) 0.02581(16) 0.01963(17) -0.00093(11) 0.00517(10) 0.01118(11) C11 0.0168(10) 0.0212(11) 0.0171(11) 0.0024(9) 0.0050(8) 0.0083(9) C12 0.0157(10) 0.0259(12) 0.0169(11) 0.0040(10) 0.0020(8) 0.0092(9) F12 0.0220(7) 0.0360(9) 0.0186(8) -0.0010(7) -0.0024(6) 0.0150(7) C13 0.0193(11) 0.0252(12) 0.0218(12) 0.0050(10) 0.0067(9) 0.0124(9) F13 0.0245(8) 0.0354(9) 0.0259(8) 0.0038(7) 0.0056(6) 0.0212(7) C14 0.0202(11) 0.0209(11) 0.0178(12) 0.0015(9) 0.0049(9) 0.0087(9) C15 0.0198(11) 0.0266(12) 0.0175(12) 0.0044(10) 0.0011(9) 0.0077(9) F15 0.0231(7) 0.0374(9) 0.0198(8) 0.0007(7) -0.0024(6) 0.0132(7) C16 0.0162(10) 0.0249(12) 0.0201(12) 0.0038(10) 0.0031(8) 0.0109(9) F16 0.0225(7) 0.0363(9) 0.0266(9) 0.0028(7) 0.0016(6) 0.0204(7) C17 0.0206(11) 0.0248(12) 0.0203(12) 0.0028(10) 0.0074(9) 0.0098(9) N17 0.0224(10) 0.0268(11) 0.0183(11) 0.0009(9) 0.0077(8) 0.0095(8) O17 0.0262(9) 0.0290(10) 0.0193(10) -0.0038(8) 0.0049(7) 0.0118(8) N21 0.0236(11) 0.0318(12) 0.0199(11) 0.0016(10) 0.0057(8) 0.0084(9) C22 0.0225(11) 0.0300(13) 0.0207(13) 0.0030(11) 0.0058(9) 0.0110(10) C23 0.0189(11) 0.0268(12) 0.0197(12) 0.0028(10) 0.0054(9) 0.0068(9) N23 0.0210(10) 0.0283(11) 0.0191(11) 0.0024(9) 0.0046(8) 0.0069(9) C24 0.0252(12) 0.0295(13) 0.0224(13) 0.0054(11) 0.0072(10) 0.0128(10) C25 0.0280(13) 0.0306(14) 0.0263(14) 0.0048(11) 0.0114(11) 0.0134(11) C26 0.0269(12) 0.0278(13) 0.0219(13) 0.0002(11) 0.0087(10) 0.0063(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.867(2) . ? Br1 O17 3.0557(19) 1_566 ? C11 C12 1.396(3) . ? C11 C16 1.400(3) . ? C11 C17 1.462(4) . ? C12 F12 1.338(3) . ? C12 C13 1.379(4) . ? C13 F13 1.340(3) . ? C13 C14 1.383(4) . ? C14 C15 1.393(3) . ? C15 F15 1.334(3) . ? C15 C16 1.377(4) . ? C16 F16 1.350(3) . ? C17 N17 1.278(3) . ? C17 H17A 0.9500 . ? N17 O17 1.387(3) . ? O17 H17 0.76(4) . ? N21 C22 1.332(4) . ? N21 C26 1.345(4) . ? C22 C23 1.386(4) . ? C22 H22 0.9500 . ? C23 C24 1.394(4) . ? C23 N23 1.427(4) . ? N23 N23 1.258(5) 2_554 ? C24 C25 1.379(4) . ? C24 H24 0.9500 . ? C25 C26 1.385(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C14 Br1 O17 158.49(9) . 1_566 ? C12 C11 C16 115.1(2) . . ? C12 C11 C17 125.5(2) . . ? C16 C11 C17 119.4(2) . . ? F12 C12 C13 117.1(2) . . ? F12 C12 C11 120.9(2) . . ? C13 C12 C11 122.0(2) . . ? F13 C13 C12 118.1(2) . . ? F13 C13 C14 119.9(2) . . ? C12 C13 C14 122.0(2) . . ? C13 C14 C15 117.2(2) . . ? C13 C14 Br1 121.19(18) . . ? C15 C14 Br1 121.54(19) . . ? F15 C15 C16 119.2(2) . . ? F15 C15 C14 120.4(2) . . ? C16 C15 C14 120.4(2) . . ? F16 C16 C15 117.8(2) . . ? F16 C16 C11 118.9(2) . . ? C15 C16 C11 123.3(2) . . ? N17 C17 C11 120.5(2) . . ? N17 C17 H17A 119.7 . . ? C11 C17 H17A 119.7 . . ? C17 N17 O17 110.5(2) . . ? N17 O17 H17 98(3) . . ? C22 N21 C26 117.7(2) . . ? N21 C22 C23 123.2(3) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C22 C23 C24 118.9(3) . . ? C22 C23 N23 115.6(2) . . ? C24 C23 N23 125.5(2) . . ? N23 N23 C23 113.5(3) 2_554 . ? C25 C24 C23 117.9(3) . . ? C25 C24 H24 121.1 . . ? C23 C24 H24 121.1 . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? N21 C26 C25 122.6(3) . . ? N21 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? 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 C16 C11 C12 F12 -178.2(2) . . . . ? C17 C11 C12 F12 -0.2(4) . . . . ? C16 C11 C12 C13 0.4(4) . . . . ? C17 C11 C12 C13 178.4(2) . . . . ? F12 C12 C13 F13 0.3(4) . . . . ? C11 C12 C13 F13 -178.4(2) . . . . ? F12 C12 C13 C14 179.1(2) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? F13 C13 C14 C15 177.3(2) . . . . ? C12 C13 C14 C15 -1.5(4) . . . . ? F13 C13 C14 Br1 0.0(4) . . . . ? C12 C13 C14 Br1 -178.8(2) . . . . ? O17 Br1 C14 C13 47.4(4) 1_566 . . . ? O17 Br1 C14 C15 -129.9(2) 1_566 . . . ? C13 C14 C15 F15 -178.7(2) . . . . ? Br1 C14 C15 F15 -1.4(4) . . . . ? C13 C14 C15 C16 1.7(4) . . . . ? Br1 C14 C15 C16 179.1(2) . . . . ? F15 C15 C16 F16 0.0(4) . . . . ? C14 C15 C16 F16 179.5(2) . . . . ? F15 C15 C16 C11 179.5(2) . . . . ? C14 C15 C16 C11 -0.9(4) . . . . ? C12 C11 C16 F16 179.4(2) . . . . ? C17 C11 C16 F16 1.3(4) . . . . ? C12 C11 C16 C15 -0.1(4) . . . . ? C17 C11 C16 C15 -178.3(2) . . . . ? C12 C11 C17 N17 2.0(4) . . . . ? C16 C11 C17 N17 179.9(3) . . . . ? C11 C17 N17 O17 -178.8(2) . . . . ? C26 N21 C22 C23 2.2(4) . . . . ? N21 C22 C23 C24 -2.9(4) . . . . ? N21 C22 C23 N23 177.5(3) . . . . ? C22 C23 N23 N23 -165.6(3) . . . 2_554 ? C24 C23 N23 N23 14.8(4) . . . 2_554 ? C22 C23 C24 C25 1.3(4) . . . . ? N23 C23 C24 C25 -179.1(3) . . . . ? C23 C24 C25 C26 0.7(4) . . . . ? C22 N21 C26 C25 0.0(4) . . . . ? C24 C25 C26 N21 -1.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O17 H17 N21 0.76(4) 1.95(4) 2.708(3) 178(4) . _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 2.155 _refine_diff_density_min -1.442 _refine_diff_density_rms 0.155 data_4,4'-azpy:COOH-I _database_code_depnum_ccdc_archive 'CCDC 906989' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-AzoPy 1-HB-XB (4-pyridyl)-N=N-(4-pyridyl), (4-I-F4-PhCOOH) ; _chemical_name_common ;4,4'-AzoPy 1-HB-XB (4-pyridyl)-N=N-(4-pyridyl), (4-I-F4- PhCOOH) ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H F4 I O2) ; _chemical_formula_sum 'C17 H9 F4 I N4 O2' _chemical_formula_weight 504.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.2112(8) _cell_length_b 8.1879(11) _cell_length_c 8.9824(12) _cell_angle_alpha 84.843(3) _cell_angle_beta 70.837(3) _cell_angle_gamma 77.402(3) _cell_volume 421.03(10) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4740 _cell_measurement_theta_min 3.60 _cell_measurement_theta_max 31.50 _exptl_crystal_description plate _exptl_crystal_colour bronze _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 1.967 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5544 _exptl_absorpt_correction_T_max 0.9255 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8655 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 31.50 _reflns_number_total 4606 _reflns_number_gt 4415 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0600P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.61(3) _refine_ls_number_reflns 4606 _refine_ls_number_parameters 207 _refine_ls_number_restraints 89 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.062 _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 N11 N 0.5934(9) 0.4231(6) 0.2876(6) 0.0362(5) Uani 1 1 d DU . . H11 H 0.5017 0.5016 0.2506 0.043 Uiso 0.50 1 calc PR . . C12 C 0.8251(11) 0.4033(7) 0.2275(6) 0.0332(5) Uani 1 1 d DU . . H12 H 0.8875 0.4760 0.1435 0.040 Uiso 1 1 calc R . . C13 C 0.9776(9) 0.2845(6) 0.2801(6) 0.0281(4) Uani 1 1 d DU . . H13 H 1.1411 0.2745 0.2345 0.034 Uiso 1 1 calc R . . C14 C 0.8816(8) 0.1780(5) 0.4046(5) 0.0234(4) Uani 1 1 d DU . . C15 C 0.6412(9) 0.1966(6) 0.4713(6) 0.0286(4) Uani 1 1 d DU . . H15 H 0.5736 0.1282 0.5577 0.034 Uiso 1 1 calc R . . C16 C 0.5050(10) 0.3201(7) 0.4055(7) 0.0354(5) Uani 1 1 d DU . . H16 H 0.3407 0.3320 0.4463 0.042 Uiso 1 1 calc R . . N14 N 1.0456(10) 0.0509(7) 0.4556(6) 0.0258(4) Uani 1 1 d D . . N21 N 1.4205(10) -0.4211(6) 0.7092(6) 0.0362(5) Uani 1 1 d D . . H21 H 1.5154 -0.4973 0.7457 0.043 Uiso 0.50 1 calc PR . . C22 C 1.1926(11) -0.4073(6) 0.7698(6) 0.0332(5) Uani 1 1 d D . . H22 H 1.1343 -0.4835 0.8516 0.040 Uiso 1 1 calc R . . C23 C 1.0322(9) -0.2854(6) 0.7189(5) 0.0281(4) Uani 1 1 d D . . H23 H 0.8693 -0.2789 0.7642 0.034 Uiso 1 1 calc R . . C24 C 1.1215(8) -0.1754(5) 0.6004(5) 0.0234(4) Uani 1 1 d D . . C25 C 1.3604(10) -0.1904(6) 0.5348(6) 0.0286(4) Uani 1 1 d D . . H25 H 1.4236 -0.1156 0.4531 0.034 Uiso 1 1 calc R . . C26 C 1.5045(10) -0.3158(7) 0.5901(7) 0.0354(5) Uani 1 1 d D . . H26 H 1.6681 -0.3285 0.5429 0.042 Uiso 1 1 calc R . . N24 N 0.9589(8) -0.0555(5) 0.5493(5) 0.0258(4) Uani 1 1 d D . . C31A C 0.1832(17) 0.8703(14) 0.0434(12) 0.0199(10) Uiso 0.3862(8) 1 d PD . 1 C32A C -0.0543(17) 0.8969(15) 0.1176(13) 0.0194(10) Uiso 0.3862(8) 1 d PD . 1 C33A C -0.215(2) 1.0213(16) 0.0621(14) 0.0221(10) Uiso 0.3862(8) 1 d PD . 1 C34A C -0.1293(18) 1.1217(15) -0.0652(14) 0.0211(10) Uiso 0.3862(8) 1 d PD . 1 C35A C 0.1098(19) 1.0941(16) -0.1364(14) 0.0222(10) Uiso 0.3862(8) 1 d PD . 1 C36A C 0.2604(19) 0.9739(14) -0.0873(12) 0.0200(10) Uiso 0.3862(8) 1 d PD . 1 C37A C 0.3514(17) 0.7492(15) 0.0998(13) 0.02352(10) Uani 0.3862(8) 1 d PD . 1 O31A O 0.2732(14) 0.6607(10) 0.2315(10) 0.02352(10) Uani 0.3862(8) 1 d PD . 1 O32A O 0.5622(12) 0.6944(9) 0.0142(8) 0.02352(10) Uani 0.3862(8) 1 d PD . 1 I1A I -0.34027(11) 1.31683(9) -0.14817(9) 0.02352(10) Uani 0.3862(8) 1 d PD . 1 F32A F -0.147(2) 0.811(3) 0.248(2) 0.0254(12) Uani 0.3862(8) 1 d PD . 1 F33A F -0.441(3) 1.054(3) 0.142(2) 0.0253(11) Uani 0.3862(8) 1 d PD . 1 F35A F 0.2160(17) 1.187(2) -0.264(2) 0.0238(10) Uani 0.3862(8) 1 d PD . 1 F36A F 0.486(3) 0.956(3) -0.1744(19) 0.0258(11) Uani 0.3862(8) 1 d PD . 1 C31B C -0.1804(11) 1.1345(10) -0.0429(9) 0.0211(10) Uiso 0.6138(8) 1 d PD . 2 C32B C 0.0602(12) 1.1050(11) -0.1171(9) 0.0222(10) Uiso 0.6138(8) 1 d PD . 2 C33B C 0.2074(12) 0.9736(9) -0.0654(8) 0.0200(10) Uiso 0.6138(8) 1 d PD . 2 C34B C 0.1261(11) 0.8724(9) 0.0651(8) 0.0199(10) Uiso 0.6138(8) 1 d PD . 2 C35B C -0.1101(11) 0.9081(9) 0.1360(8) 0.0194(10) Uiso 0.6138(8) 1 d PD . 2 C36B C -0.2601(12) 1.0306(10) 0.0866(9) 0.0221(10) Uiso 0.6138(8) 1 d PD . 2 C37B C -0.3524(11) 1.2688(9) -0.0879(9) 0.02352(10) Uani 0.6138(8) 1 d PD . 2 O31B O -0.2511(8) 1.3703(6) -0.2139(6) 0.02352(10) Uani 0.6138(8) 1 d PD . 2 O32B O -0.5608(8) 1.2813(6) -0.0381(5) 0.02352(10) Uani 0.6138(8) 1 d PD . 2 I1B I 0.34067(5) 0.68247(4) 0.14867(4) 0.02352(10) Uani 0.6138(8) 1 d PD . 2 F32B F 0.1539(8) 1.1931(12) -0.2465(11) 0.0238(10) Uani 0.6138(8) 1 d PD . 2 F33B F 0.4387(15) 0.9525(15) -0.1413(10) 0.0258(11) Uani 0.6138(8) 1 d PD . 2 F35B F -0.2051(10) 0.8116(15) 0.2619(12) 0.0254(12) Uani 0.6138(8) 1 d PD . 2 F36B F -0.4864(15) 1.0460(17) 0.1716(12) 0.0253(11) Uani 0.6138(8) 1 d PD . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0446(14) 0.0266(10) 0.0426(12) 0.0004(8) -0.0282(11) 0.0039(9) C12 0.0502(16) 0.0239(10) 0.0295(11) 0.0075(8) -0.0227(11) -0.0034(10) C13 0.0342(12) 0.0257(10) 0.0262(10) 0.0059(8) -0.0129(9) -0.0072(9) C14 0.0240(10) 0.0220(9) 0.0259(9) 0.0032(7) -0.0115(8) -0.0039(8) C15 0.0245(11) 0.0292(11) 0.0339(11) 0.0028(9) -0.0148(9) -0.0020(9) C16 0.0302(13) 0.0350(12) 0.0449(14) -0.0022(10) -0.0240(11) 0.0046(10) N14 0.0249(9) 0.0245(9) 0.0281(9) 0.0073(7) -0.0127(7) -0.0017(7) N21 0.0446(14) 0.0266(10) 0.0426(12) 0.0004(8) -0.0282(11) 0.0039(9) C22 0.0502(16) 0.0239(10) 0.0295(11) 0.0075(8) -0.0227(11) -0.0034(10) C23 0.0342(12) 0.0257(10) 0.0262(10) 0.0059(8) -0.0129(9) -0.0072(9) C24 0.0240(10) 0.0220(9) 0.0259(9) 0.0032(7) -0.0115(8) -0.0039(8) C25 0.0245(11) 0.0292(11) 0.0339(11) 0.0028(9) -0.0148(9) -0.0020(9) C26 0.0302(13) 0.0350(12) 0.0449(14) -0.0022(10) -0.0240(11) 0.0046(10) N24 0.0249(9) 0.0245(9) 0.0281(9) 0.0073(7) -0.0127(7) -0.0017(7) C37A 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) O31A 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) O32A 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) I1A 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) F32A 0.009(4) 0.0317(15) 0.034(2) 0.0162(16) -0.007(3) -0.008(3) F33A 0.018(4) 0.0303(19) 0.023(4) 0.012(3) -0.002(3) -0.008(3) F35A 0.003(3) 0.0304(16) 0.028(2) 0.0131(17) 0.001(3) 0.001(3) F36A 0.018(4) 0.0308(16) 0.020(4) 0.007(3) 0.003(2) -0.004(3) C37B 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) O31B 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) O32B 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) I1B 0.01874(13) 0.02446(16) 0.02693(17) 0.00304(10) -0.00979(10) -0.00094(9) F32B 0.003(3) 0.0304(16) 0.028(2) 0.0131(17) 0.001(3) 0.001(3) F33B 0.018(4) 0.0308(16) 0.020(4) 0.007(3) 0.003(2) -0.004(3) F35B 0.009(4) 0.0317(15) 0.034(2) 0.0162(16) -0.007(3) -0.008(3) F36B 0.018(4) 0.0303(19) 0.023(4) 0.012(3) -0.002(3) -0.008(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 N11 C12 1.339(7) . ? N11 C16 1.339(6) . ? N11 H11 0.8800 . ? C12 C13 1.369(6) . ? C12 H12 0.9500 . ? C13 C14 1.407(5) . ? C13 H13 0.9500 . ? C14 C15 1.393(6) . ? C14 N14 1.445(6) . ? C15 C16 1.391(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N14 N24 1.238(4) . ? N21 C22 1.322(7) . ? N21 C26 1.351(7) . ? N21 H21 0.8800 . ? C22 C23 1.407(6) . ? C22 H22 0.9500 . ? C23 C24 1.382(5) . ? C23 H23 0.9500 . ? C24 C25 1.387(6) . ? C24 N24 1.409(5) . ? C25 C26 1.379(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31A C32A 1.381(11) . ? C31A C36A 1.399(11) . ? C31A C37A 1.462(12) . ? C32A F32A 1.339(14) . ? C32A C33A 1.440(12) . ? C33A F33A 1.332(14) . ? C33A C34A 1.374(12) . ? C34A C35A 1.386(12) . ? C34A I1A 2.083(10) . ? C35A C36A 1.353(12) . ? C35A F35A 1.378(14) . ? C36A F36A 1.345(12) . ? C37A O32A 1.285(11) . ? C37A O31A 1.335(12) . ? I1A N21 2.796(5) 1_374 ? C31B C36B 1.396(8) . ? C31B C32B 1.397(8) . ? C31B C37B 1.485(8) . ? C32B F32B 1.341(9) . ? C32B C33B 1.403(9) . ? C33B F33B 1.352(8) . ? C33B C34B 1.392(8) . ? C34B C35B 1.370(8) . ? C34B I1B 2.074(6) . ? C35B F35B 1.362(9) . ? C35B C36B 1.362(9) . ? C36B F36B 1.346(8) . ? C37B O32B 1.207(7) . ? C37B O31B 1.399(8) . ? 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 C12 N11 C16 118.2(4) . . ? C12 N11 H11 120.9 . . ? C16 N11 H11 120.9 . . ? N11 C12 C13 123.9(5) . . ? N11 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 117.1(5) . . ? C12 C13 H13 121.4 . . ? C14 C13 H13 121.4 . . ? C15 C14 C13 120.5(4) . . ? C15 C14 N14 123.3(4) . . ? C13 C14 N14 116.2(4) . . ? C16 C15 C14 116.8(5) . . ? C16 C15 H15 121.6 . . ? C14 C15 H15 121.6 . . ? N11 C16 C15 123.4(5) . . ? N11 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? N24 N14 C14 115.1(4) . . ? C22 N21 C26 118.6(4) . . ? C22 N21 H21 120.7 . . ? C26 N21 H21 120.7 . . ? N21 C22 C23 123.2(4) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C24 C23 C22 117.3(4) . . ? C24 C23 H23 121.4 . . ? C22 C23 H23 121.4 . . ? C23 C24 C25 119.9(4) . . ? C23 C24 N24 116.6(4) . . ? C25 C24 N24 123.5(4) . . ? C26 C25 C24 118.9(5) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? N21 C26 C25 122.1(5) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? N14 N24 C24 114.0(4) . . ? C32A C31A C36A 116.2(9) . . ? C32A C31A C37A 123.6(9) . . ? C36A C31A C37A 120.1(9) . . ? F32A C32A C31A 121.3(10) . . ? F32A C32A C33A 116.4(10) . . ? C31A C32A C33A 122.2(9) . . ? F33A C33A C34A 119.1(12) . . ? F33A C33A C32A 121.3(13) . . ? C34A C33A C32A 119.1(10) . . ? C33A C34A C35A 117.6(9) . . ? C33A C34A I1A 123.1(8) . . ? C35A C34A I1A 119.3(8) . . ? C36A C35A F35A 113.7(10) . . ? C36A C35A C34A 123.4(10) . . ? F35A C35A C34A 122.9(10) . . ? F36A C36A C35A 116.2(12) . . ? F36A C36A C31A 122.3(11) . . ? C35A C36A C31A 121.4(9) . . ? O32A C37A O31A 115.8(9) . . ? O32A C37A C31A 123.6(10) . . ? O31A C37A C31A 118.7(8) . . ? C34A I1A N21 173.4(3) . 1_374 ? C36B C31B C32B 116.0(6) . . ? C36B C31B C37B 118.6(6) . . ? C32B C31B C37B 125.3(6) . . ? F32B C32B C31B 120.8(6) . . ? F32B C32B C33B 118.4(6) . . ? C31B C32B C33B 120.7(7) . . ? F33B C33B C34B 119.4(7) . . ? F33B C33B C32B 117.8(7) . . ? C34B C33B C32B 122.7(6) . . ? C35B C34B C33B 114.5(6) . . ? C35B C34B I1B 121.9(5) . . ? C33B C34B I1B 123.5(5) . . ? F35B C35B C36B 116.9(6) . . ? F35B C35B C34B 118.4(6) . . ? C36B C35B C34B 124.7(6) . . ? F36B C36B C35B 115.8(8) . . ? F36B C36B C31B 122.9(7) . . ? C35B C36B C31B 121.4(6) . . ? O32B C37B O31B 120.6(6) . . ? O32B C37B C31B 125.3(7) . . ? O31B C37B C31B 113.5(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 C16 N11 C12 C13 -0.4(7) . . . . ? N11 C12 C13 C14 0.1(8) . . . . ? C12 C13 C14 C15 -1.0(7) . . . . ? C12 C13 C14 N14 178.5(5) . . . . ? C13 C14 C15 C16 2.1(7) . . . . ? N14 C14 C15 C16 -177.4(5) . . . . ? C12 N11 C16 C15 1.7(8) . . . . ? C14 C15 C16 N11 -2.5(8) . . . . ? C15 C14 N14 N24 9.2(7) . . . . ? C13 C14 N14 N24 -170.3(4) . . . . ? C26 N21 C22 C23 -1.6(7) . . . . ? N21 C22 C23 C24 -0.4(7) . . . . ? C22 C23 C24 C25 1.3(7) . . . . ? C22 C23 C24 N24 179.1(5) . . . . ? C23 C24 C25 C26 -0.1(7) . . . . ? N24 C24 C25 C26 -177.8(5) . . . . ? C22 N21 C26 C25 2.9(7) . . . . ? C24 C25 C26 N21 -2.0(8) . . . . ? C14 N14 N24 C24 -178.4(6) . . . . ? C23 C24 N24 N14 172.6(4) . . . . ? C25 C24 N24 N14 -9.7(6) . . . . ? C36A C31A C32A F32A -176.7(15) . . . . ? C37A C31A C32A F32A 0(2) . . . . ? C36A C31A C32A C33A 1.4(19) . . . . ? C37A C31A C32A C33A 177.8(13) . . . . ? F32A C32A C33A F33A 3(3) . . . . ? C31A C32A C33A F33A -174.8(17) . . . . ? F32A C32A C33A C34A 175.6(16) . . . . ? C31A C32A C33A C34A -3(2) . . . . ? F33A C33A C34A C35A 174.0(18) . . . . ? C32A C33A C34A C35A 2(2) . . . . ? F33A C33A C34A I1A -3(2) . . . . ? C32A C33A C34A I1A -175.7(10) . . . . ? C33A C34A C35A C36A 0(2) . . . . ? I1A C34A C35A C36A 177.9(12) . . . . ? C33A C34A C35A F35A -179.8(16) . . . . ? I1A C34A C35A F35A -2(2) . . . . ? F35A C35A C36A F36A -4(2) . . . . ? C34A C35A C36A F36A 176.2(16) . . . . ? F35A C35A C36A C31A 178.5(14) . . . . ? C34A C35A C36A C31A -2(2) . . . . ? C32A C31A C36A F36A -177.0(16) . . . . ? C37A C31A C36A F36A 7(2) . . . . ? C32A C31A C36A C35A 0.6(19) . . . . ? C37A C31A C36A C35A -175.9(13) . . . . ? C32A C31A C37A O32A 162.5(12) . . . . ? C36A C31A C37A O32A -21.3(18) . . . . ? C32A C31A C37A O31A -1.1(18) . . . . ? C36A C31A C37A O31A 175.2(10) . . . . ? C33A C34A I1A N21 -166(3) . . . 1_374 ? C35A C34A I1A N21 17(4) . . . 1_374 ? C36B C31B C32B F32B 177.2(9) . . . . ? C37B C31B C32B F32B -4.8(14) . . . . ? C36B C31B C32B C33B 2.3(12) . . . . ? C37B C31B C32B C33B -179.6(8) . . . . ? F32B C32B C33B F33B 5.5(14) . . . . ? C31B C32B C33B F33B -179.5(9) . . . . ? F32B C32B C33B C34B -178.4(9) . . . . ? C31B C32B C33B C34B -3.4(13) . . . . ? F33B C33B C34B C35B 178.0(9) . . . . ? C32B C33B C34B C35B 1.9(12) . . . . ? F33B C33B C34B I1B -1.8(12) . . . . ? C32B C33B C34B I1B -177.9(7) . . . . ? C33B C34B C35B F35B 178.1(9) . . . . ? I1B C34B C35B F35B -2.1(12) . . . . ? C33B C34B C35B C36B 0.4(13) . . . . ? I1B C34B C35B C36B -179.8(7) . . . . ? F35B C35B C36B F36B 2.1(15) . . . . ? C34B C35B C36B F36B 179.8(10) . . . . ? F35B C35B C36B C31B -179.0(9) . . . . ? C34B C35B C36B C31B -1.3(14) . . . . ? C32B C31B C36B F36B 178.7(11) . . . . ? C37B C31B C36B F36B 0.5(14) . . . . ? C32B C31B C36B C35B -0.1(13) . . . . ? C37B C31B C36B C35B -178.3(8) . . . . ? C36B C31B C37B O32B -12.2(12) . . . . ? C32B C31B C37B O32B 169.8(8) . . . . ? C36B C31B C37B O31B 176.8(7) . . . . ? C32B C31B C37B O31B -1.2(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O31A 0.88 1.75 2.605(9) 164.3 . N21 H21 O31B 0.88 1.73 2.598(6) 167.5 1_736 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.080 _refine_diff_density_min -1.020 _refine_diff_density_rms 0.127 data_4,4'-azpy:COOH-Br _database_code_depnum_ccdc_archive 'CCDC 906990' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H9 Br F4 N4 O2' _chemical_formula_weight 457.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1601(6) _cell_length_b 13.4584(8) _cell_length_c 14.4512(10) _cell_angle_alpha 112.181(4) _cell_angle_beta 90.560(4) _cell_angle_gamma 111.547(4) _cell_volume 1676.47(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 3.967 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5354 _exptl_absorpt_correction_T_max 0.7420 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12739 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 68.96 _reflns_number_total 5428 _reflns_number_gt 4522 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0800P)^2^+8.0000P] 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 5428 _refine_ls_number_parameters 646 _refine_ls_number_restraints 408 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.2362 _refine_ls_wR_factor_gt 0.2270 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11A_1 N 0.8898(14) 0.3918(8) 0.3801(10) 0.053(3) Uani 0.786(3) 1 d PD A 1 C12A_1 C 0.9643(17) 0.4108(11) 0.3081(12) 0.057(3) Uani 0.786(3) 1 d PD A 1 H12A_1 H 0.9844 0.4822 0.3013 0.068 Uiso 0.786(3) 1 calc PR A 1 C13A_1 C 1.0125(14) 0.3328(8) 0.2444(8) 0.051(3) Uani 0.786(3) 1 d PD A 1 H13A_1 H 1.0605 0.3478 0.1921 0.061 Uiso 0.786(3) 1 calc PR A 1 C14A_1 C 0.9906(11) 0.2314(8) 0.2569(8) 0.051(3) Uani 0.786(3) 1 d PD A 1 C15A_1 C 0.9152(16) 0.2085(12) 0.3310(13) 0.056(3) Uani 0.786(3) 1 d PD A 1 H15A_1 H 0.8983 0.1392 0.3409 0.068 Uiso 0.786(3) 1 calc PR A 1 C16A_1 C 0.8645(19) 0.2928(12) 0.3914(12) 0.050(3) Uani 0.786(3) 1 d PD A 1 H16A_1 H 0.8105 0.2784 0.4417 0.060 Uiso 0.786(3) 1 calc PR A 1 N14A_1 N 1.0447(10) 0.1450(7) 0.1997(6) 0.053(2) Uani 0.786(3) 1 d PD A 1 N21A_1 N 1.2788(11) -0.0638(10) -0.0528(9) 0.059(3) Uani 0.786(3) 1 d PD A 1 C22A_1 C 1.204(2) -0.0892(14) 0.0162(15) 0.068(4) Uani 0.786(3) 1 d PD A 1 H22A_1 H 1.1894 -0.1616 0.0195 0.082 Uiso 0.786(3) 1 calc PR A 1 C23A_1 C 1.1465(19) -0.0210(13) 0.0822(11) 0.057(3) Uani 0.786(3) 1 d PD A 1 H23A_1 H 1.0927 -0.0451 0.1290 0.069 Uiso 0.786(3) 1 calc PR A 1 C24A_1 C 1.1699(15) 0.0874(9) 0.0785(9) 0.053(3) Uani 0.786(3) 1 d PD A 1 C25A_1 C 1.2507(17) 0.1179(11) 0.0098(12) 0.063(3) Uani 0.786(3) 1 d PD A 1 H25A_1 H 1.2726 0.1917 0.0074 0.076 Uiso 0.786(3) 1 calc PR A 1 C26A_1 C 1.299(2) 0.0385(14) -0.0554(12) 0.069(4) Uani 0.786(3) 1 d PD A 1 H26A_1 H 1.3497 0.0581 -0.1051 0.083 Uiso 0.786(3) 1 calc PR A 1 N24A_1 N 1.1148(9) 0.1720(6) 0.1398(6) 0.050(2) Uani 0.786(3) 1 d PD A 1 N11B_1 N 0.865(6) 0.363(4) 0.389(5) 0.053(3) Uani 0.214(3) 1 d PD A 2 C12B_1 C 0.878(8) 0.267(6) 0.389(5) 0.050(3) Uani 0.214(3) 1 d PD A 2 H12B_1 H 0.8346 0.2365 0.4353 0.060 Uiso 0.214(3) 1 calc PR A 2 C13B_1 C 0.951(8) 0.213(4) 0.325(5) 0.056(3) Uani 0.214(3) 1 d PD A 2 H13B_1 H 0.9500 0.1408 0.3222 0.068 Uiso 0.214(3) 1 calc PR A 2 C14B_1 C 1.028(4) 0.263(2) 0.264(3) 0.051(3) Uani 0.214(3) 1 d PD A 2 C15B_1 C 1.029(6) 0.368(3) 0.269(4) 0.051(3) Uani 0.214(3) 1 d PD A 2 H15B_1 H 1.0904 0.4108 0.2361 0.061 Uiso 0.214(3) 1 calc PR A 2 C16B_1 C 0.933(7) 0.409(5) 0.327(5) 0.057(3) Uani 0.214(3) 1 d PD A 2 H16B_1 H 0.9162 0.4717 0.3211 0.068 Uiso 0.214(3) 1 calc PR A 2 N14B_1 N 1.085(4) 0.205(2) 0.178(2) 0.053(2) Uani 0.214(3) 1 d PD A 2 N21B_1 N 1.311(5) -0.044(4) -0.033(4) 0.059(3) Uani 0.214(3) 1 d PD A 2 C22B_1 C 1.299(9) 0.052(6) -0.032(6) 0.069(4) Uani 0.214(3) 1 d PD A 2 H22B_1 H 1.3526 0.0877 -0.0730 0.083 Uiso 0.214(3) 1 calc PR A 2 C23B_1 C 1.217(7) 0.104(5) 0.024(4) 0.063(3) Uani 0.214(3) 1 d PD A 2 H23B_1 H 1.2043 0.1667 0.0163 0.076 Uiso 0.214(3) 1 calc PR A 2 C24B_1 C 1.152(6) 0.060(3) 0.094(3) 0.053(3) Uani 0.214(3) 1 d PD A 2 C25B_1 C 1.160(8) -0.041(5) 0.092(5) 0.057(3) Uani 0.214(3) 1 d PD A 2 H25B_1 H 1.1171 -0.0737 0.1382 0.069 Uiso 0.214(3) 1 calc PR A 2 C26B_1 C 1.231(9) -0.093(5) 0.022(6) 0.068(4) Uani 0.214(3) 1 d PD A 2 H26B_1 H 1.2222 -0.1695 0.0123 0.082 Uiso 0.214(3) 1 calc PR A 2 N24B_1 N 1.080(3) 0.112(2) 0.173(2) 0.050(2) Uani 0.214(3) 1 d PD A 2 Br1A_1 Br 0.41943(13) 0.81015(10) 0.81724(8) 0.0516(4) Uani 0.786(3) 1 d PD A 1 C31A_1 C 0.6339(10) 0.5772(6) 0.6045(7) 0.054(2) Uani 0.786(3) 1 d PGD A 1 C32A_1 C 0.5427(10) 0.5375(6) 0.6656(6) 0.057(3) Uani 0.786(3) 1 d PGD A 1 C33A_1 C 0.4802(8) 0.6078(6) 0.7287(5) 0.050(3) Uani 0.786(3) 1 d PGD A 1 C34A_1 C 0.5088(9) 0.7179(6) 0.7307(6) 0.051(2) Uani 0.786(3) 1 d PGD A 1 C35A_1 C 0.6000(10) 0.7577(5) 0.6696(7) 0.055(3) Uani 0.786(3) 1 d PGD A 1 C36A_1 C 0.6625(9) 0.6873(5) 0.6065(6) 0.052(3) Uani 0.786(3) 1 d PGD A 1 C37A_1 C 0.703(2) 0.5003(14) 0.5400(15) 0.0636(10) Uani 0.786(3) 1 d PD A 1 O31A_1 O 0.7805(9) 0.5357(7) 0.4819(6) 0.0636(10) Uani 0.786(3) 1 d PD A 1 H31A_1 H 0.8315 0.4972 0.4621 0.076 Uiso 0.786(3) 1 calc PR A 1 O32A_1 O 0.6881(9) 0.4052(6) 0.5429(6) 0.0636(10) Uani 0.786(3) 1 d PD A 1 F32A_1 F 0.5045(10) 0.4315(6) 0.6632(6) 0.074(3) Uani 0.786(3) 1 d PD A 1 F33A_1 F 0.3808(16) 0.5635(9) 0.7785(11) 0.077(5) Uani 0.786(3) 1 d PD A 1 F35A_1 F 0.6313(13) 0.8637(7) 0.6734(11) 0.070(4) Uani 0.786(3) 1 d PD A 1 F36A_1 F 0.756(4) 0.7343(13) 0.557(3) 0.077(5) Uani 0.786(3) 1 d PD A 1 Br1B_1 Br 0.7325(8) 0.4968(5) 0.5189(5) 0.0636(10) Uani 0.214(3) 1 d PD A 2 C31B_1 C 0.496(3) 0.7170(19) 0.721(3) 0.051(2) Uani 0.214(3) 1 d PD A 2 C32B_1 C 0.621(4) 0.7706(16) 0.689(3) 0.055(3) Uani 0.214(3) 1 d PD A 2 C33B_1 C 0.689(4) 0.7036(15) 0.628(4) 0.052(3) Uani 0.214(3) 1 d PD A 2 C34B_1 C 0.645(3) 0.5863(14) 0.611(3) 0.054(2) Uani 0.214(3) 1 d PD A 2 C35B_1 C 0.521(4) 0.5333(18) 0.643(4) 0.057(3) Uani 0.214(3) 1 d PD A 2 C36B_1 C 0.451(3) 0.5995(19) 0.702(3) 0.050(3) Uani 0.214(3) 1 d PD A 2 C37B_1 C 0.426(3) 0.792(2) 0.787(2) 0.0516(4) Uani 0.214(3) 1 d PD A 2 O31B_1 O 0.394(3) 0.7785(19) 0.8668(15) 0.0516(4) Uani 0.214(3) 1 d PD A 2 H31B_1 H 0.3584 0.8258 0.8991 0.062 Uiso 0.214(3) 1 calc PR A 2 O32B_1 O 0.427(3) 0.8807(17) 0.7775(17) 0.0516(4) Uani 0.214(3) 1 d PD A 2 F32B_1 F 0.660(6) 0.878(3) 0.693(6) 0.070(4) Uani 0.214(3) 1 d PD A 2 F33B_1 F 0.773(15) 0.745(5) 0.569(10) 0.077(5) Uani 0.214(3) 1 d PD A 2 F35B_1 F 0.480(4) 0.423(2) 0.631(4) 0.074(3) Uani 0.214(3) 1 d PD A 2 F36B_1 F 0.361(8) 0.551(3) 0.753(6) 0.077(5) Uani 0.214(3) 1 d PD A 2 N11A_2 N 0.6658(9) 0.1811(9) 0.7222(7) 0.054(2) Uani 0.812(3) 1 d PD B 1 C12A_2 C 0.5601(11) 0.0820(11) 0.7156(10) 0.058(3) Uani 0.812(3) 1 d PD B 1 H12A_2 H 0.5728 0.0476 0.7597 0.070 Uiso 0.812(3) 1 calc PR B 1 C13A_2 C 0.4352(16) 0.0285(16) 0.6483(17) 0.061(3) Uani 0.812(3) 1 d PD B 1 H13A_2 H 0.3617 -0.0407 0.6472 0.074 Uiso 0.812(3) 1 calc PR B 1 C14A_2 C 0.4157(11) 0.0751(12) 0.5818(9) 0.061(3) Uani 0.812(3) 1 d PD B 1 C15A_2 C 0.5213(12) 0.1793(14) 0.5873(14) 0.060(4) Uani 0.812(3) 1 d PD B 1 H15A_2 H 0.5099 0.2149 0.5440 0.072 Uiso 0.812(3) 1 calc PR B 1 C16A_2 C 0.6467(13) 0.2296(12) 0.6607(10) 0.055(3) Uani 0.812(3) 1 d PD B 1 H16A_2 H 0.7204 0.3011 0.6664 0.066 Uiso 0.812(3) 1 calc PR B 1 N14A_2 N 0.2902(9) 0.0312(7) 0.5068(7) 0.066(3) Uani 0.812(3) 1 d PD B 1 N21A_2 N -0.1783(13) -0.2027(10) 0.2860(12) 0.056(3) Uani 0.812(3) 1 d PD B 1 C22A_2 C -0.071(2) -0.104(2) 0.294(2) 0.065(3) Uani 0.812(3) 1 d PD B 1 H22A_2 H -0.0830 -0.0699 0.2501 0.078 Uiso 0.812(3) 1 calc PR B 1 C23A_2 C 0.0545(18) -0.0501(15) 0.3603(18) 0.065(4) Uani 0.812(3) 1 d PD B 1 H23A_2 H 0.1265 0.0208 0.3635 0.078 Uiso 0.812(3) 1 calc PR B 1 C24A_2 C 0.0745(12) -0.1025(12) 0.4242(11) 0.061(3) Uani 0.812(3) 1 d PD B 1 C25A_2 C -0.0319(15) -0.2075(16) 0.4140(16) 0.069(3) Uani 0.812(3) 1 d PD B 1 H25A_2 H -0.0203 -0.2474 0.4534 0.082 Uiso 0.812(3) 1 calc PR B 1 C26A_2 C -0.1553(13) -0.2526(15) 0.3448(16) 0.066(4) Uani 0.812(3) 1 d PD B 1 H26A_2 H -0.2291 -0.3243 0.3387 0.079 Uiso 0.812(3) 1 calc PR B 1 N24A_2 N 0.1990(9) -0.0597(8) 0.5009(7) 0.068(3) Uani 0.812(3) 1 d PD B 1 N11B_2 N 0.687(3) 0.197(6) 0.696(4) 0.054(2) Uani 0.188(3) 1 d PD B 2 C12B_2 C 0.627(5) 0.227(6) 0.634(6) 0.055(3) Uani 0.188(3) 1 d PD B 2 H12B_2 H 0.6847 0.2926 0.6208 0.066 Uiso 0.188(3) 1 calc PR B 2 C13B_2 C 0.486(6) 0.169(6) 0.589(7) 0.060(4) Uani 0.188(3) 1 d PD B 2 H13B_2 H 0.4456 0.1970 0.5501 0.072 Uiso 0.188(3) 1 calc PR B 2 C14B_2 C 0.403(4) 0.068(4) 0.600(4) 0.061(3) Uani 0.188(3) 1 d PD B 2 C15B_2 C 0.463(6) 0.031(7) 0.661(8) 0.061(3) Uani 0.188(3) 1 d PD B 2 H15B_2 H 0.4113 -0.0411 0.6662 0.074 Uiso 0.188(3) 1 calc PR B 2 C16B_2 C 0.604(4) 0.106(6) 0.715(5) 0.058(3) Uani 0.188(3) 1 d PD B 2 H16B_2 H 0.6415 0.0905 0.7663 0.070 Uiso 0.188(3) 1 calc PR B 2 N14B_2 N 0.265(4) -0.017(3) 0.539(3) 0.066(3) Uani 0.188(3) 1 d PD B 2 N21B_2 N -0.165(7) -0.224(6) 0.277(6) 0.056(3) Uani 0.188(3) 1 d PD B 2 C22B_2 C -0.120(8) -0.251(7) 0.347(8) 0.066(4) Uani 0.188(3) 1 d PD B 2 H22B_2 H -0.1787 -0.3232 0.3497 0.079 Uiso 0.188(3) 1 calc PR B 2 C23B_2 C 0.002(7) -0.183(7) 0.417(8) 0.069(3) Uani 0.188(3) 1 d PD B 2 H23B_2 H 0.0292 -0.2065 0.4654 0.082 Uiso 0.188(3) 1 calc PR B 2 C24B_2 C 0.089(6) -0.075(5) 0.414(6) 0.061(3) Uani 0.188(3) 1 d PD B 2 C25B_2 C 0.034(8) -0.038(6) 0.351(8) 0.065(4) Uani 0.188(3) 1 d PD B 2 H25B_2 H 0.0829 0.0383 0.3531 0.078 Uiso 0.188(3) 1 calc PR B 2 C26B_2 C -0.094(11) -0.115(8) 0.285(10) 0.065(3) Uani 0.188(3) 1 d PD B 2 H26B_2 H -0.1331 -0.0886 0.2441 0.078 Uiso 0.188(3) 1 calc PR B 2 N24B_2 N 0.229(4) 0.007(4) 0.474(3) 0.068(3) Uani 0.188(3) 1 d PD B 2 Br2A_2 Br 1.55757(12) 0.67026(10) 1.15425(8) 0.0483(4) Uani 0.812(3) 1 d PD B 1 C31A_2 C 1.1157(10) 0.4453(7) 0.9314(10) 0.048(3) Uani 0.812(3) 1 d PD B 1 C32A_2 C 1.1923(12) 0.5621(8) 0.9493(13) 0.050(2) Uani 0.812(3) 1 d PD B 1 C33A_2 C 1.3248(12) 0.6261(7) 1.0131(12) 0.051(2) Uani 0.812(3) 1 d PD B 1 C34A_2 C 1.3786(10) 0.5775(7) 1.0653(10) 0.048(2) Uani 0.812(3) 1 d PD B 1 C35A_2 C 1.3004(14) 0.4621(9) 1.0496(14) 0.051(2) Uani 0.812(3) 1 d PD B 1 C36A_2 C 1.1697(8) 0.3970(7) 0.9841(8) 0.051(3) Uani 0.812(3) 1 d PD B 1 C37A_2 C 0.9806(17) 0.3746(13) 0.8541(14) 0.0653(11) Uani 0.812(3) 1 d PD B 1 O31A_2 O 0.8972(8) 0.2796(6) 0.8560(6) 0.0653(11) Uani 0.812(3) 1 d PD B 1 H31A_2 H 0.8227 0.2498 0.8126 0.078 Uiso 0.812(3) 1 calc PR B 1 O32A_2 O 0.9480(8) 0.4084(7) 0.7915(6) 0.0653(11) Uani 0.812(3) 1 d PD B 1 F32A_2 F 1.1440(11) 0.6172(6) 0.9081(5) 0.063(3) Uani 0.812(3) 1 d PD B 1 F33A_2 F 1.393(2) 0.7401(9) 1.0332(19) 0.0649(18) Uani 0.812(3) 1 d PD B 1 F35A_2 F 1.350(2) 0.4128(11) 1.0976(19) 0.065(3) Uani 0.812(3) 1 d PD B 1 F36A_2 F 1.1047(11) 0.2872(7) 0.9713(10) 0.065(3) Uani 0.812(3) 1 d PD B 1 Br1B_2 Br 0.9453(7) 0.3463(6) 0.8377(6) 0.0653(11) Uani 0.188(3) 1 d PD B 2 C31B_2 C 1.377(4) 0.593(3) 1.066(4) 0.048(2) Uani 0.188(3) 1 d PD B 2 C32B_2 C 1.310(6) 0.475(3) 1.048(6) 0.051(2) Uani 0.188(3) 1 d PD B 2 C33B_2 C 1.193(4) 0.400(3) 0.971(4) 0.051(3) Uani 0.188(3) 1 d PD B 2 C34B_2 C 1.129(4) 0.445(2) 0.920(5) 0.048(3) Uani 0.188(3) 1 d PD B 2 C35B_2 C 1.192(5) 0.563(3) 0.941(5) 0.050(2) Uani 0.188(3) 1 d PD B 2 C36B_2 C 1.313(5) 0.637(2) 1.015(5) 0.051(2) Uani 0.188(3) 1 d PD B 2 C37B_2 C 1.527(3) 0.662(3) 1.126(4) 0.095(11) Uani 0.188(3) 1 d PD B 2 O31B_2 O 1.567(3) 0.626(3) 1.185(2) 0.095(11) Uani 0.188(3) 1 d PD B 2 H31B_2 H 1.6499 0.6744 1.2172 0.114 Uiso 0.188(3) 1 calc PR B 2 O32B_2 O 1.614(3) 0.746(2) 1.112(3) 0.095(11) Uani 0.188(3) 1 d PD B 2 F32B_2 F 1.365(10) 0.425(5) 1.092(9) 0.065(3) Uani 0.188(3) 1 d PD B 2 F33B_2 F 1.127(6) 0.288(3) 0.958(6) 0.065(3) Uani 0.188(3) 1 d PD B 2 F35B_2 F 1.149(5) 0.604(2) 0.881(4) 0.063(3) Uani 0.188(3) 1 d PD B 2 F36B_2 F 1.376(9) 0.744(4) 1.021(9) 0.0649(18) Uani 0.188(3) 1 d PD B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11A_1 0.049(6) 0.045(6) 0.061(5) 0.022(5) 0.013(4) 0.015(6) C12A_1 0.046(9) 0.060(5) 0.078(9) 0.047(6) 0.023(5) 0.015(5) C13A_1 0.052(6) 0.049(7) 0.047(7) 0.022(6) 0.012(5) 0.013(6) C14A_1 0.039(7) 0.046(6) 0.057(5) 0.017(5) 0.010(5) 0.009(5) C15A_1 0.042(11) 0.055(5) 0.073(6) 0.029(4) 0.018(6) 0.017(6) C16A_1 0.050(6) 0.050(9) 0.056(5) 0.028(6) 0.015(4) 0.021(5) N14A_1 0.062(6) 0.053(5) 0.054(5) 0.022(4) 0.015(4) 0.032(5) N21A_1 0.035(7) 0.051(6) 0.066(7) 0.006(5) 0.009(6) 0.009(5) C22A_1 0.044(10) 0.057(5) 0.102(8) 0.034(5) 0.007(7) 0.015(5) C23A_1 0.056(7) 0.059(8) 0.066(6) 0.034(5) 0.015(5) 0.023(5) C24A_1 0.050(6) 0.047(6) 0.065(7) 0.025(5) 0.021(4) 0.021(6) C25A_1 0.047(10) 0.059(6) 0.080(8) 0.034(5) 0.015(5) 0.014(7) C26A_1 0.056(6) 0.066(8) 0.054(11) 0.012(8) 0.006(7) 0.003(6) N24A_1 0.034(5) 0.042(5) 0.068(6) 0.031(4) -0.004(4) -0.001(4) N11B_1 0.049(6) 0.045(6) 0.061(5) 0.022(5) 0.013(4) 0.015(6) C12B_1 0.050(6) 0.050(9) 0.056(5) 0.028(6) 0.015(4) 0.021(5) C13B_1 0.042(11) 0.055(5) 0.073(6) 0.029(4) 0.018(6) 0.017(6) C14B_1 0.039(7) 0.046(6) 0.057(5) 0.017(5) 0.010(5) 0.009(5) C15B_1 0.052(6) 0.049(7) 0.047(7) 0.022(6) 0.012(5) 0.013(6) C16B_1 0.046(9) 0.060(5) 0.078(9) 0.047(6) 0.023(5) 0.015(5) N14B_1 0.062(6) 0.053(5) 0.054(5) 0.022(4) 0.015(4) 0.032(5) N21B_1 0.035(7) 0.051(6) 0.066(7) 0.006(5) 0.009(6) 0.009(5) C22B_1 0.056(6) 0.066(8) 0.054(11) 0.012(8) 0.006(7) 0.003(6) C23B_1 0.047(10) 0.059(6) 0.080(8) 0.034(5) 0.015(5) 0.014(7) C24B_1 0.050(6) 0.047(6) 0.065(7) 0.025(5) 0.021(4) 0.021(6) C25B_1 0.056(7) 0.059(8) 0.066(6) 0.034(5) 0.015(5) 0.023(5) C26B_1 0.044(10) 0.057(5) 0.102(8) 0.034(5) 0.007(7) 0.015(5) N24B_1 0.034(5) 0.042(5) 0.068(6) 0.031(4) -0.004(4) -0.001(4) Br1A_1 0.0461(7) 0.0486(6) 0.0601(7) 0.0240(5) 0.0164(5) 0.0169(5) C31A_1 0.042(5) 0.056(5) 0.058(5) 0.026(4) 0.008(4) 0.011(4) C32A_1 0.064(7) 0.059(5) 0.061(7) 0.039(5) 0.020(6) 0.025(5) C33A_1 0.053(6) 0.054(5) 0.047(6) 0.032(4) 0.011(5) 0.015(4) C34A_1 0.040(5) 0.059(5) 0.053(5) 0.024(4) 0.017(4) 0.019(4) C35A_1 0.048(6) 0.047(5) 0.060(7) 0.023(5) 0.002(5) 0.006(4) C36A_1 0.044(6) 0.053(5) 0.045(7) 0.020(4) 0.012(5) 0.004(4) C37A_1 0.066(3) 0.0573(17) 0.070(3) 0.0276(16) 0.0199(17) 0.0257(17) O31A_1 0.066(3) 0.0573(17) 0.070(3) 0.0276(16) 0.0199(17) 0.0257(17) O32A_1 0.066(3) 0.0573(17) 0.070(3) 0.0276(16) 0.0199(17) 0.0257(17) F32A_1 0.094(6) 0.062(3) 0.089(8) 0.046(4) 0.046(6) 0.037(4) F33A_1 0.090(7) 0.063(4) 0.094(10) 0.047(5) 0.055(8) 0.031(4) F35A_1 0.078(7) 0.057(3) 0.091(8) 0.044(5) 0.039(7) 0.028(4) F36A_1 0.085(10) 0.064(4) 0.098(9) 0.047(6) 0.053(9) 0.031(6) Br1B_1 0.066(3) 0.0573(17) 0.070(3) 0.0276(16) 0.0199(17) 0.0257(17) C31B_1 0.040(5) 0.059(5) 0.053(5) 0.024(4) 0.017(4) 0.019(4) C32B_1 0.048(6) 0.047(5) 0.060(7) 0.023(5) 0.002(5) 0.006(4) C33B_1 0.044(6) 0.053(5) 0.045(7) 0.020(4) 0.012(5) 0.004(4) C34B_1 0.042(5) 0.056(5) 0.058(5) 0.026(4) 0.008(4) 0.011(4) C35B_1 0.064(7) 0.059(5) 0.061(7) 0.039(5) 0.020(6) 0.025(5) C36B_1 0.053(6) 0.054(5) 0.047(6) 0.032(4) 0.011(5) 0.015(4) C37B_1 0.0461(7) 0.0486(6) 0.0601(7) 0.0240(5) 0.0164(5) 0.0169(5) O31B_1 0.0461(7) 0.0486(6) 0.0601(7) 0.0240(5) 0.0164(5) 0.0169(5) O32B_1 0.0461(7) 0.0486(6) 0.0601(7) 0.0240(5) 0.0164(5) 0.0169(5) F32B_1 0.078(7) 0.057(3) 0.091(8) 0.044(5) 0.039(7) 0.028(4) F33B_1 0.085(10) 0.064(4) 0.098(9) 0.047(6) 0.053(9) 0.031(6) F35B_1 0.094(6) 0.062(3) 0.089(8) 0.046(4) 0.046(6) 0.037(4) F36B_1 0.090(7) 0.063(4) 0.094(10) 0.047(5) 0.055(8) 0.031(4) N11A_2 0.048(5) 0.055(6) 0.052(6) 0.020(4) 0.014(4) 0.016(5) C12A_2 0.051(8) 0.049(7) 0.071(6) 0.027(5) 0.020(7) 0.013(6) C13A_2 0.055(8) 0.057(5) 0.073(9) 0.027(5) 0.016(6) 0.022(6) C14A_2 0.050(6) 0.059(5) 0.058(7) 0.009(5) 0.009(5) 0.021(5) C15A_2 0.061(9) 0.055(6) 0.071(6) 0.029(5) 0.021(7) 0.025(6) C16A_2 0.050(6) 0.048(5) 0.052(10) 0.017(6) 0.015(5) 0.008(5) N14A_2 0.073(8) 0.055(6) 0.069(7) 0.025(5) 0.034(5) 0.023(5) N21A_2 0.043(5) 0.053(7) 0.066(6) 0.022(5) 0.006(4) 0.017(4) C22A_2 0.064(11) 0.078(8) 0.055(8) 0.030(7) 0.018(6) 0.028(7) C23A_2 0.047(8) 0.047(6) 0.077(8) 0.015(5) 0.023(5) 0.006(5) C24A_2 0.047(6) 0.068(9) 0.056(6) 0.016(5) 0.004(5) 0.020(6) C25A_2 0.057(10) 0.083(10) 0.072(6) 0.047(8) 0.014(7) 0.019(6) C26A_2 0.049(10) 0.064(6) 0.072(6) 0.025(5) 0.023(7) 0.011(6) N24A_2 0.070(7) 0.061(6) 0.080(7) 0.039(5) 0.037(5) 0.023(5) N11B_2 0.048(5) 0.055(6) 0.052(6) 0.020(4) 0.014(4) 0.016(5) C12B_2 0.050(6) 0.048(5) 0.052(10) 0.017(6) 0.015(5) 0.008(5) C13B_2 0.061(9) 0.055(6) 0.071(6) 0.029(5) 0.021(7) 0.025(6) C14B_2 0.050(6) 0.059(5) 0.058(7) 0.009(5) 0.009(5) 0.021(5) C15B_2 0.055(8) 0.057(5) 0.073(9) 0.027(5) 0.016(6) 0.022(6) C16B_2 0.051(8) 0.049(7) 0.071(6) 0.027(5) 0.020(7) 0.013(6) N14B_2 0.073(8) 0.055(6) 0.069(7) 0.025(5) 0.034(5) 0.023(5) N21B_2 0.043(5) 0.053(7) 0.066(6) 0.022(5) 0.006(4) 0.017(4) C22B_2 0.049(10) 0.064(6) 0.072(6) 0.025(5) 0.023(7) 0.011(6) C23B_2 0.057(10) 0.083(10) 0.072(6) 0.047(8) 0.014(7) 0.019(6) C24B_2 0.047(6) 0.068(9) 0.056(6) 0.016(5) 0.004(5) 0.020(6) C25B_2 0.047(8) 0.047(6) 0.077(8) 0.015(5) 0.023(5) 0.006(5) C26B_2 0.064(11) 0.078(8) 0.055(8) 0.030(7) 0.018(6) 0.028(7) N24B_2 0.070(7) 0.061(6) 0.080(7) 0.039(5) 0.037(5) 0.023(5) Br2A_2 0.0381(6) 0.0453(6) 0.0556(7) 0.0223(5) 0.0081(4) 0.0090(4) C31A_2 0.037(5) 0.054(4) 0.055(6) 0.028(4) 0.016(4) 0.012(4) C32A_2 0.040(5) 0.055(4) 0.058(5) 0.032(4) 0.007(4) 0.014(4) C33A_2 0.044(5) 0.040(4) 0.065(5) 0.026(4) 0.010(4) 0.009(4) C34A_2 0.032(4) 0.048(5) 0.051(4) 0.017(4) 0.006(3) 0.006(4) C35A_2 0.044(5) 0.047(5) 0.062(5) 0.032(4) 0.011(4) 0.008(4) C36A_2 0.037(5) 0.055(5) 0.056(6) 0.026(4) 0.017(4) 0.010(4) C37A_2 0.047(3) 0.072(3) 0.069(2) 0.031(2) 0.0052(17) 0.013(2) O31A_2 0.047(3) 0.072(3) 0.069(2) 0.031(2) 0.0052(17) 0.013(2) O32A_2 0.047(3) 0.072(3) 0.069(2) 0.031(2) 0.0052(17) 0.013(2) F32A_2 0.067(3) 0.058(3) 0.058(6) 0.027(3) -0.003(4) 0.016(3) F33A_2 0.061(6) 0.049(3) 0.082(8) 0.041(3) 0.000(3) 0.004(3) F35A_2 0.060(6) 0.051(4) 0.085(5) 0.041(4) -0.001(5) 0.008(3) F36A_2 0.052(5) 0.051(3) 0.088(6) 0.043(3) 0.004(5) 0.001(3) Br1B_2 0.047(3) 0.072(3) 0.069(2) 0.031(2) 0.0052(17) 0.013(2) C31B_2 0.032(4) 0.048(5) 0.051(4) 0.017(4) 0.006(3) 0.006(4) C32B_2 0.044(5) 0.047(5) 0.062(5) 0.032(4) 0.011(4) 0.008(4) C33B_2 0.037(5) 0.055(5) 0.056(6) 0.026(4) 0.017(4) 0.010(4) C34B_2 0.037(5) 0.054(4) 0.055(6) 0.028(4) 0.016(4) 0.012(4) C35B_2 0.040(5) 0.055(4) 0.058(5) 0.032(4) 0.007(4) 0.014(4) C36B_2 0.044(5) 0.040(4) 0.065(5) 0.026(4) 0.010(4) 0.009(4) C37B_2 0.066(17) 0.048(13) 0.11(2) -0.027(15) 0.012(15) 0.017(11) O31B_2 0.066(17) 0.048(13) 0.11(2) -0.027(15) 0.012(15) 0.017(11) O32B_2 0.066(17) 0.048(13) 0.11(2) -0.027(15) 0.012(15) 0.017(11) F32B_2 0.060(6) 0.051(4) 0.085(5) 0.041(4) -0.001(5) 0.008(3) F33B_2 0.052(5) 0.051(3) 0.088(6) 0.043(3) 0.004(5) 0.001(3) F35B_2 0.067(3) 0.058(3) 0.058(6) 0.027(3) -0.003(4) 0.016(3) F36B_2 0.061(6) 0.049(3) 0.082(8) 0.041(3) 0.000(3) 0.004(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 N11A_1 C12A_1 1.340(11) . ? N11A_1 C16A_1 1.335(11) . ? C12A_1 C13A_1 1.358(14) . ? C12A_1 H12A_1 0.9500 . ? C13A_1 C14A_1 1.382(13) . ? C13A_1 H13A_1 0.9500 . ? C14A_1 C15A_1 1.387(12) . ? C14A_1 N14A_1 1.446(11) . ? C15A_1 C16A_1 1.416(14) . ? C15A_1 H15A_1 0.9500 . ? C16A_1 H16A_1 0.9500 . ? N14A_1 N24A_1 1.203(9) . ? N21A_1 C26A_1 1.330(13) . ? N21A_1 C22A_1 1.332(13) . ? C22A_1 C23A_1 1.355(14) . ? C22A_1 H22A_1 0.9500 . ? C23A_1 C24A_1 1.410(13) . ? C23A_1 H23A_1 0.9500 . ? C24A_1 C25A_1 1.381(12) . ? C24A_1 N24A_1 1.453(11) . ? C25A_1 C26A_1 1.379(14) . ? C25A_1 H25A_1 0.9500 . ? C26A_1 H26A_1 0.9500 . ? N11B_1 C12B_1 1.340(11) . ? N11B_1 C16B_1 1.335(12) . ? C12B_1 C13B_1 1.359(14) . ? C12B_1 H12B_1 0.9500 . ? C13B_1 C14B_1 1.381(14) . ? C13B_1 H13B_1 0.9500 . ? C14B_1 C15B_1 1.390(13) . ? C14B_1 N14B_1 1.446(11) . ? C15B_1 C16B_1 1.416(14) . ? C15B_1 H15B_1 0.9500 . ? C16B_1 H16B_1 0.9500 . ? N14B_1 N24B_1 1.203(9) . ? N21B_1 C26B_1 1.331(14) . ? N21B_1 C22B_1 1.332(14) . ? C22B_1 C23B_1 1.355(14) . ? C22B_1 H22B_1 0.9500 . ? C23B_1 C24B_1 1.410(14) . ? C23B_1 H23B_1 0.9500 . ? C24B_1 C25B_1 1.381(13) . ? C24B_1 N24B_1 1.454(11) . ? C25B_1 C26B_1 1.380(15) . ? C25B_1 H25B_1 0.9500 . ? C26B_1 H26B_1 0.9500 . ? Br1A_1 C34A_1 1.900(5) . ? C31A_1 C32A_1 1.3900 . ? C31A_1 C36A_1 1.3900 . ? C31A_1 C37A_1 1.503(13) . ? C32A_1 F32A_1 1.320(7) . ? C32A_1 C33A_1 1.3900 . ? C33A_1 F33A_1 1.337(7) . ? C33A_1 C34A_1 1.3900 . ? C34A_1 C35A_1 1.3900 . ? C35A_1 F35A_1 1.322(7) . ? C35A_1 C36A_1 1.3900 . ? C36A_1 F36A_1 1.311(7) . ? C37A_1 O32A_1 1.248(15) . ? C37A_1 O31A_1 1.260(14) . ? O31A_1 H31A_1 0.8400 . ? Br1B_1 C34B_1 1.897(6) . ? C31B_1 C32B_1 1.390(5) . ? C31B_1 C36B_1 1.390(4) . ? C31B_1 C37B_1 1.501(14) . ? C32B_1 F32B_1 1.322(8) . ? C32B_1 C33B_1 1.390(5) . ? C33B_1 F33B_1 1.341(8) . ? C33B_1 C34B_1 1.390(5) . ? C34B_1 C35B_1 1.389(5) . ? C35B_1 F35B_1 1.325(8) . ? C35B_1 C36B_1 1.388(4) . ? C36B_1 F36B_1 1.314(8) . ? C37B_1 O32B_1 1.248(15) . ? C37B_1 O31B_1 1.260(14) . ? O31B_1 H31B_1 0.8400 . ? N11A_2 C12A_2 1.339(11) . ? N11A_2 C16A_2 1.334(11) . ? C12A_2 C13A_2 1.360(14) . ? C12A_2 H12A_2 0.9500 . ? C13A_2 C14A_2 1.378(13) . ? C13A_2 H13A_2 0.9500 . ? C14A_2 C15A_2 1.390(12) . ? C14A_2 N14A_2 1.445(11) . ? C15A_2 C16A_2 1.415(14) . ? C15A_2 H15A_2 0.9500 . ? C16A_2 H16A_2 0.9500 . ? N14A_2 N24A_2 1.204(9) . ? N21A_2 C26A_2 1.331(13) . ? N21A_2 C22A_2 1.332(13) . ? C22A_2 C23A_2 1.355(14) . ? C22A_2 H22A_2 0.9500 . ? C23A_2 C24A_2 1.409(14) . ? C23A_2 H23A_2 0.9500 . ? C24A_2 C25A_2 1.380(12) . ? C24A_2 N24A_2 1.455(11) . ? C25A_2 C26A_2 1.378(14) . ? C25A_2 H25A_2 0.9500 . ? C26A_2 H26A_2 0.9500 . ? N11B_2 C12B_2 1.340(11) . ? N11B_2 C16B_2 1.335(12) . ? C12B_2 C13B_2 1.359(14) . ? C12B_2 H12B_2 0.9500 . ? C13B_2 C14B_2 1.381(14) . ? C13B_2 H13B_2 0.9500 . ? C14B_2 C15B_2 1.389(13) . ? C14B_2 N14B_2 1.447(11) . ? C15B_2 C16B_2 1.416(14) . ? C15B_2 H15B_2 0.9500 . ? C16B_2 H16B_2 0.9500 . ? N14B_2 N24B_2 1.205(9) . ? N21B_2 C26B_2 1.331(14) . ? N21B_2 C22B_2 1.333(14) . ? C22B_2 C23B_2 1.356(14) . ? C22B_2 H22B_2 0.9500 . ? C23B_2 C24B_2 1.410(14) . ? C23B_2 H23B_2 0.9500 . ? C24B_2 C25B_2 1.381(13) . ? C24B_2 N24B_2 1.453(11) . ? C25B_2 C26B_2 1.379(15) . ? C25B_2 H25B_2 0.9500 . ? C26B_2 H26B_2 0.9500 . ? Br2A_2 C34A_2 1.895(6) . ? C31A_2 C32A_2 1.391(4) . ? C31A_2 C36A_2 1.390(4) . ? C31A_2 C37A_2 1.499(14) . ? C32A_2 F32A_2 1.320(7) . ? C32A_2 C33A_2 1.388(4) . ? C33A_2 F33A_2 1.340(7) . ? C33A_2 C34A_2 1.388(4) . ? C34A_2 C35A_2 1.385(4) . ? C35A_2 F35A_2 1.326(7) . ? C35A_2 C36A_2 1.387(4) . ? C36A_2 F36A_2 1.314(7) . ? C37A_2 O32A_2 1.245(15) . ? C37A_2 O31A_2 1.259(14) . ? O31A_2 H31A_2 0.8400 . ? Br1B_2 C34B_2 1.896(7) . ? C31B_2 C32B_2 1.390(5) . ? C31B_2 C36B_2 1.391(4) . ? C31B_2 C37B_2 1.501(14) . ? C32B_2 F32B_2 1.321(8) . ? C32B_2 C33B_2 1.389(5) . ? C33B_2 F33B_2 1.340(8) . ? C33B_2 C34B_2 1.390(5) . ? C34B_2 C35B_2 1.388(4) . ? C35B_2 F35B_2 1.324(8) . ? C35B_2 C36B_2 1.388(5) . ? C36B_2 F36B_2 1.314(8) . ? C37B_2 O32B_2 1.247(15) . ? C37B_2 O31B_2 1.258(14) . ? O31B_2 H31B_2 0.8400 . ? 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 C12A_1 N11A_1 C16A_1 118.6(7) . . ? N11A_1 C12A_1 C13A_1 123.0(8) . . ? N11A_1 C12A_1 H12A_1 118.5 . . ? C13A_1 C12A_1 H12A_1 118.5 . . ? C12A_1 C13A_1 C14A_1 119.1(8) . . ? C12A_1 C13A_1 H13A_1 120.4 . . ? C14A_1 C13A_1 H13A_1 120.4 . . ? C13A_1 C14A_1 C15A_1 119.8(7) . . ? C13A_1 C14A_1 N14A_1 125.1(8) . . ? C15A_1 C14A_1 N14A_1 115.1(9) . . ? C14A_1 C15A_1 C16A_1 117.1(8) . . ? C14A_1 C15A_1 H15A_1 121.4 . . ? C16A_1 C15A_1 H15A_1 121.4 . . ? N11A_1 C16A_1 C15A_1 122.3(8) . . ? N11A_1 C16A_1 H16A_1 118.9 . . ? C15A_1 C16A_1 H16A_1 118.9 . . ? N24A_1 N14A_1 C14A_1 112.3(7) . . ? C26A_1 N21A_1 C22A_1 116.0(7) . . ? N21A_1 C22A_1 C23A_1 125.8(10) . . ? N21A_1 C22A_1 H22A_1 117.1 . . ? C23A_1 C22A_1 H22A_1 117.1 . . ? C22A_1 C23A_1 C24A_1 117.1(9) . . ? C22A_1 C23A_1 H23A_1 121.4 . . ? C24A_1 C23A_1 H23A_1 121.4 . . ? C25A_1 C24A_1 C23A_1 118.5(7) . . ? C25A_1 C24A_1 N24A_1 115.2(8) . . ? C23A_1 C24A_1 N24A_1 126.3(8) . . ? C26A_1 C25A_1 C24A_1 118.4(9) . . ? C26A_1 C25A_1 H25A_1 120.8 . . ? C24A_1 C25A_1 H25A_1 120.8 . . ? N21A_1 C26A_1 C25A_1 124.0(9) . . ? N21A_1 C26A_1 H26A_1 118.0 . . ? C25A_1 C26A_1 H26A_1 118.0 . . ? N14A_1 N24A_1 C24A_1 114.9(7) . . ? C12B_1 N11B_1 C16B_1 118.2(8) . . ? N11B_1 C12B_1 C13B_1 122.8(10) . . ? N11B_1 C12B_1 H12B_1 118.6 . . ? C13B_1 C12B_1 H12B_1 118.6 . . ? C12B_1 C13B_1 C14B_1 119.6(10) . . ? C12B_1 C13B_1 H13B_1 120.2 . . ? C14B_1 C13B_1 H13B_1 120.2 . . ? C13B_1 C14B_1 C15B_1 119.2(8) . . ? C13B_1 C14B_1 N14B_1 125.9(11) . . ? C15B_1 C14B_1 N14B_1 113.7(11) . . ? C14B_1 C15B_1 C16B_1 116.7(11) . . ? C14B_1 C15B_1 H15B_1 121.7 . . ? C16B_1 C15B_1 H15B_1 121.7 . . ? N11B_1 C16B_1 C15B_1 122.4(11) . . ? N11B_1 C16B_1 H16B_1 118.8 . . ? C15B_1 C16B_1 H16B_1 118.8 . . ? N24B_1 N14B_1 C14B_1 113.2(10) . . ? C26B_1 N21B_1 C22B_1 115.8(9) . . ? N21B_1 C22B_1 C23B_1 125.2(11) . . ? N21B_1 C22B_1 H22B_1 117.4 . . ? C23B_1 C22B_1 H22B_1 117.4 . . ? C22B_1 C23B_1 C24B_1 117.4(11) . . ? C22B_1 C23B_1 H23B_1 121.3 . . ? C24B_1 C23B_1 H23B_1 121.3 . . ? C25B_1 C24B_1 C23B_1 118.4(8) . . ? C25B_1 C24B_1 N24B_1 114.7(10) . . ? C23B_1 C24B_1 N24B_1 126.8(10) . . ? C26B_1 C25B_1 C24B_1 117.8(11) . . ? C26B_1 C25B_1 H25B_1 121.1 . . ? C24B_1 C25B_1 H25B_1 121.1 . . ? N21B_1 C26B_1 C25B_1 124.0(12) . . ? N21B_1 C26B_1 H26B_1 118.0 . . ? C25B_1 C26B_1 H26B_1 118.0 . . ? N14B_1 N24B_1 C24B_1 113.7(9) . . ? C32A_1 C31A_1 C36A_1 120.0 . . ? C32A_1 C31A_1 C37A_1 118.4(6) . . ? C36A_1 C31A_1 C37A_1 121.6(6) . . ? F32A_1 C32A_1 C31A_1 123.1(4) . . ? F32A_1 C32A_1 C33A_1 116.8(4) . . ? C31A_1 C32A_1 C33A_1 120.0 . . ? F33A_1 C33A_1 C32A_1 119.2(4) . . ? F33A_1 C33A_1 C34A_1 120.4(5) . . ? C32A_1 C33A_1 C34A_1 120.0 . . ? C35A_1 C34A_1 C33A_1 120.0 . . ? C35A_1 C34A_1 Br1A_1 121.6(3) . . ? C33A_1 C34A_1 Br1A_1 118.4(3) . . ? F35A_1 C35A_1 C36A_1 119.6(4) . . ? F35A_1 C35A_1 C34A_1 120.4(4) . . ? C36A_1 C35A_1 C34A_1 120.0 . . ? F36A_1 C36A_1 C35A_1 116.6(5) . . ? F36A_1 C36A_1 C31A_1 123.2(5) . . ? C35A_1 C36A_1 C31A_1 120.0 . . ? O32A_1 C37A_1 O31A_1 119.9(11) . . ? O32A_1 C37A_1 C31A_1 122.7(10) . . ? O31A_1 C37A_1 C31A_1 117.4(11) . . ? C37A_1 O31A_1 H31A_1 109.5 . . ? C32B_1 C31B_1 C36B_1 119.1(6) . . ? C32B_1 C31B_1 C37B_1 118.8(8) . . ? C36B_1 C31B_1 C37B_1 121.5(8) . . ? F32B_1 C32B_1 C31B_1 121.9(9) . . ? F32B_1 C32B_1 C33B_1 116.2(9) . . ? C31B_1 C32B_1 C33B_1 119.9(6) . . ? F33B_1 C33B_1 C32B_1 118.5(9) . . ? F33B_1 C33B_1 C34B_1 119.4(9) . . ? C32B_1 C33B_1 C34B_1 120.4(6) . . ? C35B_1 C34B_1 C33B_1 118.9(6) . . ? C35B_1 C34B_1 Br1B_1 121.4(7) . . ? C33B_1 C34B_1 Br1B_1 118.3(7) . . ? F35B_1 C35B_1 C36B_1 119.1(8) . . ? F35B_1 C35B_1 C34B_1 119.8(8) . . ? C36B_1 C35B_1 C34B_1 120.3(6) . . ? F36B_1 C36B_1 C35B_1 116.2(9) . . ? F36B_1 C36B_1 C31B_1 122.4(9) . . ? C35B_1 C36B_1 C31B_1 120.3(5) . . ? O32B_1 C37B_1 O31B_1 119.1(13) . . ? O32B_1 C37B_1 C31B_1 121.9(12) . . ? O31B_1 C37B_1 C31B_1 117.0(12) . . ? C37B_1 O31B_1 H31B_1 109.5 . . ? C12A_2 N11A_2 C16A_2 118.4(7) . . ? N11A_2 C12A_2 C13A_2 122.7(8) . . ? N11A_2 C12A_2 H12A_2 118.7 . . ? C13A_2 C12A_2 H12A_2 118.7 . . ? C14A_2 C13A_2 C12A_2 119.7(9) . . ? C14A_2 C13A_2 H13A_2 120.1 . . ? C12A_2 C13A_2 H13A_2 120.1 . . ? C13A_2 C14A_2 C15A_2 119.6(7) . . ? C13A_2 C14A_2 N14A_2 127.2(8) . . ? C15A_2 C14A_2 N14A_2 113.2(9) . . ? C14A_2 C15A_2 C16A_2 116.8(8) . . ? C14A_2 C15A_2 H15A_2 121.6 . . ? C16A_2 C15A_2 H15A_2 121.6 . . ? N11A_2 C16A_2 C15A_2 122.9(8) . . ? N11A_2 C16A_2 H16A_2 118.6 . . ? C15A_2 C16A_2 H16A_2 118.6 . . ? N24A_2 N14A_2 C14A_2 113.4(8) . . ? C26A_2 N21A_2 C22A_2 116.1(7) . . ? N21A_2 C22A_2 C23A_2 125.1(10) . . ? N21A_2 C22A_2 H22A_2 117.5 . . ? C23A_2 C22A_2 H22A_2 117.5 . . ? C22A_2 C23A_2 C24A_2 117.7(9) . . ? C22A_2 C23A_2 H23A_2 121.1 . . ? C24A_2 C23A_2 H23A_2 121.1 . . ? C25A_2 C24A_2 C23A_2 118.6(7) . . ? C25A_2 C24A_2 N24A_2 114.2(8) . . ? C23A_2 C24A_2 N24A_2 127.2(8) . . ? C26A_2 C25A_2 C24A_2 117.9(9) . . ? C26A_2 C25A_2 H25A_2 121.1 . . ? C24A_2 C25A_2 H25A_2 121.1 . . ? N21A_2 C26A_2 C25A_2 124.5(9) . . ? N21A_2 C26A_2 H26A_2 117.8 . . ? C25A_2 C26A_2 H26A_2 117.8 . . ? N14A_2 N24A_2 C24A_2 112.3(7) . . ? C12B_2 N11B_2 C16B_2 118.3(9) . . ? N11B_2 C12B_2 C13B_2 122.8(10) . . ? N11B_2 C12B_2 H12B_2 118.6 . . ? C13B_2 C12B_2 H12B_2 118.6 . . ? C12B_2 C13B_2 C14B_2 119.4(10) . . ? C12B_2 C13B_2 H13B_2 120.3 . . ? C14B_2 C13B_2 H13B_2 120.3 . . ? C13B_2 C14B_2 C15B_2 119.5(9) . . ? C13B_2 C14B_2 N14B_2 125.5(11) . . ? C15B_2 C14B_2 N14B_2 114.1(12) . . ? C14B_2 C15B_2 C16B_2 116.8(10) . . ? C14B_2 C15B_2 H15B_2 121.6 . . ? C16B_2 C15B_2 H15B_2 121.6 . . ? N11B_2 C16B_2 C15B_2 122.3(11) . . ? N11B_2 C16B_2 H16B_2 118.9 . . ? C15B_2 C16B_2 H16B_2 118.9 . . ? N24B_2 N14B_2 C14B_2 112.4(10) . . ? C26B_2 N21B_2 C22B_2 115.9(10) . . ? N21B_2 C22B_2 C23B_2 125.2(12) . . ? N21B_2 C22B_2 H22B_2 117.4 . . ? C23B_2 C22B_2 H22B_2 117.4 . . ? C22B_2 C23B_2 C24B_2 117.2(11) . . ? C22B_2 C23B_2 H23B_2 121.4 . . ? C24B_2 C23B_2 H23B_2 121.4 . . ? C25B_2 C24B_2 C23B_2 118.4(9) . . ? C25B_2 C24B_2 N24B_2 114.7(10) . . ? C23B_2 C24B_2 N24B_2 126.8(10) . . ? C26B_2 C25B_2 C24B_2 118.0(11) . . ? C26B_2 C25B_2 H25B_2 121.0 . . ? C24B_2 C25B_2 H25B_2 121.0 . . ? N21B_2 C26B_2 C25B_2 123.9(11) . . ? N21B_2 C26B_2 H26B_2 118.0 . . ? C25B_2 C26B_2 H26B_2 118.0 . . ? N14B_2 N24B_2 C24B_2 113.8(10) . . ? C32A_2 C31A_2 C36A_2 118.6(4) . . ? C32A_2 C31A_2 C37A_2 119.4(6) . . ? C36A_2 C31A_2 C37A_2 122.0(7) . . ? F32A_2 C32A_2 C33A_2 117.1(5) . . ? F32A_2 C32A_2 C31A_2 122.5(5) . . ? C33A_2 C32A_2 C31A_2 120.4(4) . . ? F33A_2 C33A_2 C34A_2 119.7(5) . . ? F33A_2 C33A_2 C32A_2 119.1(5) . . ? C34A_2 C33A_2 C32A_2 120.8(4) . . ? C35A_2 C34A_2 C33A_2 118.8(4) . . ? C35A_2 C34A_2 Br2A_2 122.2(4) . . ? C33A_2 C34A_2 Br2A_2 119.0(4) . . ? F35A_2 C35A_2 C36A_2 119.3(5) . . ? F35A_2 C35A_2 C34A_2 120.1(5) . . ? C36A_2 C35A_2 C34A_2 120.6(4) . . ? F36A_2 C36A_2 C35A_2 116.6(5) . . ? F36A_2 C36A_2 C31A_2 122.6(5) . . ? C35A_2 C36A_2 C31A_2 120.8(4) . . ? O32A_2 C37A_2 O31A_2 120.2(11) . . ? O32A_2 C37A_2 C31A_2 122.3(10) . . ? O31A_2 C37A_2 C31A_2 117.5(11) . . ? C37A_2 O31A_2 H31A_2 109.5 . . ? C32B_2 C31B_2 C36B_2 118.9(5) . . ? C32B_2 C31B_2 C37B_2 118.8(9) . . ? C36B_2 C31B_2 C37B_2 121.4(8) . . ? F32B_2 C32B_2 C33B_2 116.7(9) . . ? F32B_2 C32B_2 C31B_2 122.5(9) . . ? C33B_2 C32B_2 C31B_2 120.1(7) . . ? F33B_2 C33B_2 C34B_2 119.7(9) . . ? F33B_2 C33B_2 C32B_2 118.9(9) . . ? C34B_2 C33B_2 C32B_2 120.4(7) . . ? C35B_2 C34B_2 C33B_2 119.0(5) . . ? C35B_2 C34B_2 Br1B_2 121.8(7) . . ? C33B_2 C34B_2 Br1B_2 118.6(7) . . ? F35B_2 C35B_2 C36B_2 119.2(9) . . ? F35B_2 C35B_2 C34B_2 119.9(9) . . ? C36B_2 C35B_2 C34B_2 120.4(5) . . ? F36B_2 C36B_2 C35B_2 116.2(9) . . ? F36B_2 C36B_2 C31B_2 122.3(10) . . ? C35B_2 C36B_2 C31B_2 120.4(7) . . ? O32B_2 C37B_2 O31B_2 119.7(13) . . ? O32B_2 C37B_2 C31B_2 122.4(12) . . ? O31B_2 C37B_2 C31B_2 117.7(11) . . ? C37B_2 O31B_2 H31B_2 109.5 . . ? 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 C16A_1 N11A_1 C12A_1 C13A_1 2(3) . . . . ? N11A_1 C12A_1 C13A_1 C14A_1 -3(2) . . . . ? C12A_1 C13A_1 C14A_1 C15A_1 2.6(19) . . . . ? C12A_1 C13A_1 C14A_1 N14A_1 -175.4(14) . . . . ? C13A_1 C14A_1 C15A_1 C16A_1 0(2) . . . . ? N14A_1 C14A_1 C15A_1 C16A_1 177.8(14) . . . . ? C12A_1 N11A_1 C16A_1 C15A_1 1(3) . . . . ? C14A_1 C15A_1 C16A_1 N11A_1 -1(3) . . . . ? C13A_1 C14A_1 N14A_1 N24A_1 1.3(17) . . . . ? C15A_1 C14A_1 N14A_1 N24A_1 -176.7(12) . . . . ? C26A_1 N21A_1 C22A_1 C23A_1 1(3) . . . . ? N21A_1 C22A_1 C23A_1 C24A_1 -1(3) . . . . ? C22A_1 C23A_1 C24A_1 C25A_1 -1(2) . . . . ? C22A_1 C23A_1 C24A_1 N24A_1 178.0(15) . . . . ? C23A_1 C24A_1 C25A_1 C26A_1 3(2) . . . . ? N24A_1 C24A_1 C25A_1 C26A_1 -176.0(16) . . . . ? C22A_1 N21A_1 C26A_1 C25A_1 2(3) . . . . ? C24A_1 C25A_1 C26A_1 N21A_1 -4(3) . . . . ? C14A_1 N14A_1 N24A_1 C24A_1 -178.9(10) . . . . ? C25A_1 C24A_1 N24A_1 N14A_1 -179.9(13) . . . . ? C23A_1 C24A_1 N24A_1 N14A_1 1(2) . . . . ? C16B_1 N11B_1 C12B_1 C13B_1 -3(13) . . . . ? N11B_1 C12B_1 C13B_1 C14B_1 7(12) . . . . ? C12B_1 C13B_1 C14B_1 C15B_1 0(9) . . . . ? C12B_1 C13B_1 C14B_1 N14B_1 -166(7) . . . . ? C13B_1 C14B_1 C15B_1 C16B_1 -9(6) . . . . ? N14B_1 C14B_1 C15B_1 C16B_1 159(6) . . . . ? C12B_1 N11B_1 C16B_1 C15B_1 -6(11) . . . . ? C14B_1 C15B_1 C16B_1 N11B_1 13(9) . . . . ? C13B_1 C14B_1 N14B_1 N24B_1 -11(6) . . . . ? C15B_1 C14B_1 N14B_1 N24B_1 -178(4) . . . . ? C26B_1 N21B_1 C22B_1 C23B_1 3(12) . . . . ? N21B_1 C22B_1 C23B_1 C24B_1 7(12) . . . . ? C22B_1 C23B_1 C24B_1 C25B_1 -8(9) . . . . ? C22B_1 C23B_1 C24B_1 N24B_1 169(7) . . . . ? C23B_1 C24B_1 C25B_1 C26B_1 0(10) . . . . ? N24B_1 C24B_1 C25B_1 C26B_1 -178(6) . . . . ? C22B_1 N21B_1 C26B_1 C25B_1 -12(10) . . . . ? C24B_1 C25B_1 C26B_1 N21B_1 11(11) . . . . ? C14B_1 N14B_1 N24B_1 C24B_1 -173(4) . . . . ? C25B_1 C24B_1 N24B_1 N14B_1 174(6) . . . . ? C23B_1 C24B_1 N24B_1 N14B_1 -3(8) . . . . ? C36A_1 C31A_1 C32A_1 F32A_1 176.0(10) . . . . ? C37A_1 C31A_1 C32A_1 F32A_1 -6.1(14) . . . . ? C36A_1 C31A_1 C32A_1 C33A_1 0.0 . . . . ? C37A_1 C31A_1 C32A_1 C33A_1 177.9(14) . . . . ? F32A_1 C32A_1 C33A_1 F33A_1 -3.5(13) . . . . ? C31A_1 C32A_1 C33A_1 F33A_1 172.8(12) . . . . ? F32A_1 C32A_1 C33A_1 C34A_1 -176.3(10) . . . . ? C31A_1 C32A_1 C33A_1 C34A_1 0.0 . . . . ? F33A_1 C33A_1 C34A_1 C35A_1 -172.7(12) . . . . ? C32A_1 C33A_1 C34A_1 C35A_1 0.0 . . . . ? F33A_1 C33A_1 C34A_1 Br1A_1 6.8(12) . . . . ? C32A_1 C33A_1 C34A_1 Br1A_1 179.4(7) . . . . ? C33A_1 C34A_1 C35A_1 F35A_1 -177.9(11) . . . . ? Br1A_1 C34A_1 C35A_1 F35A_1 2.7(10) . . . . ? C33A_1 C34A_1 C35A_1 C36A_1 0.0 . . . . ? Br1A_1 C34A_1 C35A_1 C36A_1 -179.4(7) . . . . ? F35A_1 C35A_1 C36A_1 F36A_1 3(2) . . . . ? C34A_1 C35A_1 C36A_1 F36A_1 -175(2) . . . . ? F35A_1 C35A_1 C36A_1 C31A_1 177.9(11) . . . . ? C34A_1 C35A_1 C36A_1 C31A_1 0.0 . . . . ? C32A_1 C31A_1 C36A_1 F36A_1 174(2) . . . . ? C37A_1 C31A_1 C36A_1 F36A_1 -4(3) . . . . ? C32A_1 C31A_1 C36A_1 C35A_1 0.0 . . . . ? C37A_1 C31A_1 C36A_1 C35A_1 -177.9(14) . . . . ? C32A_1 C31A_1 C37A_1 O32A_1 -4(3) . . . . ? C36A_1 C31A_1 C37A_1 O32A_1 174.3(15) . . . . ? C32A_1 C31A_1 C37A_1 O31A_1 176.9(14) . . . . ? C36A_1 C31A_1 C37A_1 O31A_1 -5(3) . . . . ? C36B_1 C31B_1 C32B_1 F32B_1 172(5) . . . . ? C37B_1 C31B_1 C32B_1 F32B_1 -17(5) . . . . ? C36B_1 C31B_1 C32B_1 C33B_1 9(5) . . . . ? C37B_1 C31B_1 C32B_1 C33B_1 180(4) . . . . ? F32B_1 C32B_1 C33B_1 F33B_1 -9(7) . . . . ? C31B_1 C32B_1 C33B_1 F33B_1 156(8) . . . . ? F32B_1 C32B_1 C33B_1 C34B_1 -174(5) . . . . ? C31B_1 C32B_1 C33B_1 C34B_1 -9(5) . . . . ? F33B_1 C33B_1 C34B_1 C35B_1 -156(8) . . . . ? C32B_1 C33B_1 C34B_1 C35B_1 9(5) . . . . ? F33B_1 C33B_1 C34B_1 Br1B_1 11(7) . . . . ? C32B_1 C33B_1 C34B_1 Br1B_1 175(4) . . . . ? C33B_1 C34B_1 C35B_1 F35B_1 -177(5) . . . . ? Br1B_1 C34B_1 C35B_1 F35B_1 16(6) . . . . ? C33B_1 C34B_1 C35B_1 C36B_1 -7(5) . . . . ? Br1B_1 C34B_1 C35B_1 C36B_1 -174(4) . . . . ? F35B_1 C35B_1 C36B_1 F36B_1 8(7) . . . . ? C34B_1 C35B_1 C36B_1 F36B_1 -162(6) . . . . ? F35B_1 C35B_1 C36B_1 C31B_1 177(5) . . . . ? C34B_1 C35B_1 C36B_1 C31B_1 7(5) . . . . ? C32B_1 C31B_1 C36B_1 F36B_1 161(6) . . . . ? C37B_1 C31B_1 C36B_1 F36B_1 -10(6) . . . . ? C32B_1 C31B_1 C36B_1 C35B_1 -7(5) . . . . ? C37B_1 C31B_1 C36B_1 C35B_1 -178(4) . . . . ? C32B_1 C31B_1 C37B_1 O32B_1 34(4) . . . . ? C36B_1 C31B_1 C37B_1 O32B_1 -155(4) . . . . ? C32B_1 C31B_1 C37B_1 O31B_1 -130(4) . . . . ? C36B_1 C31B_1 C37B_1 O31B_1 41(4) . . . . ? C16A_2 N11A_2 C12A_2 C13A_2 1(2) . . . . ? N11A_2 C12A_2 C13A_2 C14A_2 2(3) . . . . ? C12A_2 C13A_2 C14A_2 C15A_2 -3(3) . . . . ? C12A_2 C13A_2 C14A_2 N14A_2 -179.0(18) . . . . ? C13A_2 C14A_2 C15A_2 C16A_2 2(2) . . . . ? N14A_2 C14A_2 C15A_2 C16A_2 178.5(17) . . . . ? C12A_2 N11A_2 C16A_2 C15A_2 -2(2) . . . . ? C14A_2 C15A_2 C16A_2 N11A_2 0(3) . . . . ? C13A_2 C14A_2 N14A_2 N24A_2 -4(2) . . . . ? C15A_2 C14A_2 N14A_2 N24A_2 179.2(13) . . . . ? C26A_2 N21A_2 C22A_2 C23A_2 -3(4) . . . . ? N21A_2 C22A_2 C23A_2 C24A_2 1(5) . . . . ? C22A_2 C23A_2 C24A_2 C25A_2 2(3) . . . . ? C22A_2 C23A_2 C24A_2 N24A_2 -180(3) . . . . ? C23A_2 C24A_2 C25A_2 C26A_2 -3(3) . . . . ? N24A_2 C24A_2 C25A_2 C26A_2 178(2) . . . . ? C22A_2 N21A_2 C26A_2 C25A_2 2(3) . . . . ? C24A_2 C25A_2 C26A_2 N21A_2 1(4) . . . . ? C14A_2 N14A_2 N24A_2 C24A_2 -179.4(13) . . . . ? C25A_2 C24A_2 N24A_2 N14A_2 179.1(17) . . . . ? C23A_2 C24A_2 N24A_2 N14A_2 1(3) . . . . ? C16B_2 N11B_2 C12B_2 C13B_2 0(14) . . . . ? N11B_2 C12B_2 C13B_2 C14B_2 -6(14) . . . . ? C12B_2 C13B_2 C14B_2 C15B_2 3(10) . . . . ? C12B_2 C13B_2 C14B_2 N14B_2 -165(9) . . . . ? C13B_2 C14B_2 C15B_2 C16B_2 5(11) . . . . ? N14B_2 C14B_2 C15B_2 C16B_2 174(8) . . . . ? C12B_2 N11B_2 C16B_2 C15B_2 9(10) . . . . ? C14B_2 C15B_2 C16B_2 N11B_2 -11(11) . . . . ? C13B_2 C14B_2 N14B_2 N24B_2 2(8) . . . . ? C15B_2 C14B_2 N14B_2 N24B_2 -166(7) . . . . ? C26B_2 N21B_2 C22B_2 C23B_2 -10(14) . . . . ? N21B_2 C22B_2 C23B_2 C24B_2 0(19) . . . . ? C22B_2 C23B_2 C24B_2 C25B_2 9(13) . . . . ? C22B_2 C23B_2 C24B_2 N24B_2 -174(11) . . . . ? C23B_2 C24B_2 C25B_2 C26B_2 -8(14) . . . . ? N24B_2 C24B_2 C25B_2 C26B_2 175(12) . . . . ? C22B_2 N21B_2 C26B_2 C25B_2 11(14) . . . . ? C24B_2 C25B_2 C26B_2 N21B_2 -2(20) . . . . ? C14B_2 N14B_2 N24B_2 C24B_2 -178(6) . . . . ? C25B_2 C24B_2 N24B_2 N14B_2 168(9) . . . . ? C23B_2 C24B_2 N24B_2 N14B_2 -8(13) . . . . ? C36A_2 C31A_2 C32A_2 F32A_2 -175.1(17) . . . . ? C37A_2 C31A_2 C32A_2 F32A_2 7(2) . . . . ? C36A_2 C31A_2 C32A_2 C33A_2 4.5(19) . . . . ? C37A_2 C31A_2 C32A_2 C33A_2 -173.6(17) . . . . ? F32A_2 C32A_2 C33A_2 F33A_2 3(2) . . . . ? C31A_2 C32A_2 C33A_2 F33A_2 -176.5(17) . . . . ? F32A_2 C32A_2 C33A_2 C34A_2 175.2(17) . . . . ? C31A_2 C32A_2 C33A_2 C34A_2 -4(2) . . . . ? F33A_2 C33A_2 C34A_2 C35A_2 174.7(17) . . . . ? C32A_2 C33A_2 C34A_2 C35A_2 3(2) . . . . ? F33A_2 C33A_2 C34A_2 Br2A_2 -6(2) . . . . ? C32A_2 C33A_2 C34A_2 Br2A_2 -178.3(13) . . . . ? C33A_2 C34A_2 C35A_2 F35A_2 179.2(19) . . . . ? Br2A_2 C34A_2 C35A_2 F35A_2 0(2) . . . . ? C33A_2 C34A_2 C35A_2 C36A_2 -1(2) . . . . ? Br2A_2 C34A_2 C35A_2 C36A_2 179.9(15) . . . . ? F35A_2 C35A_2 C36A_2 F36A_2 -2(2) . . . . ? C34A_2 C35A_2 C36A_2 F36A_2 178.0(15) . . . . ? F35A_2 C35A_2 C36A_2 C31A_2 -179.0(17) . . . . ? C34A_2 C35A_2 C36A_2 C31A_2 1(2) . . . . ? C32A_2 C31A_2 C36A_2 F36A_2 -179.5(13) . . . . ? C37A_2 C31A_2 C36A_2 F36A_2 -1(2) . . . . ? C32A_2 C31A_2 C36A_2 C35A_2 -2.9(19) . . . . ? C37A_2 C31A_2 C36A_2 C35A_2 175.1(17) . . . . ? C32A_2 C31A_2 C37A_2 O32A_2 14(3) . . . . ? C36A_2 C31A_2 C37A_2 O32A_2 -164.0(16) . . . . ? C32A_2 C31A_2 C37A_2 O31A_2 -164.0(16) . . . . ? C36A_2 C31A_2 C37A_2 O31A_2 18(3) . . . . ? C36B_2 C31B_2 C32B_2 F32B_2 179(8) . . . . ? C37B_2 C31B_2 C32B_2 F32B_2 9(9) . . . . ? C36B_2 C31B_2 C32B_2 C33B_2 8(7) . . . . ? C37B_2 C31B_2 C32B_2 C33B_2 -161(7) . . . . ? F32B_2 C32B_2 C33B_2 F33B_2 12(9) . . . . ? C31B_2 C32B_2 C33B_2 F33B_2 -177(7) . . . . ? F32B_2 C32B_2 C33B_2 C34B_2 -180(8) . . . . ? C31B_2 C32B_2 C33B_2 C34B_2 -9(8) . . . . ? F33B_2 C33B_2 C34B_2 C35B_2 175(6) . . . . ? C32B_2 C33B_2 C34B_2 C35B_2 6(7) . . . . ? F33B_2 C33B_2 C34B_2 Br1B_2 2(7) . . . . ? C32B_2 C33B_2 C34B_2 Br1B_2 -166(6) . . . . ? C33B_2 C34B_2 C35B_2 F35B_2 168(7) . . . . ? Br1B_2 C34B_2 C35B_2 F35B_2 -20(7) . . . . ? C33B_2 C34B_2 C35B_2 C36B_2 -4(6) . . . . ? Br1B_2 C34B_2 C35B_2 C36B_2 168(6) . . . . ? F35B_2 C35B_2 C36B_2 F36B_2 0(8) . . . . ? C34B_2 C35B_2 C36B_2 F36B_2 172(7) . . . . ? F35B_2 C35B_2 C36B_2 C31B_2 -168(7) . . . . ? C34B_2 C35B_2 C36B_2 C31B_2 4(7) . . . . ? C32B_2 C31B_2 C36B_2 F36B_2 -173(7) . . . . ? C37B_2 C31B_2 C36B_2 F36B_2 -4(8) . . . . ? C32B_2 C31B_2 C36B_2 C35B_2 -6(6) . . . . ? C37B_2 C31B_2 C36B_2 C35B_2 163(6) . . . . ? C32B_2 C31B_2 C37B_2 O32B_2 150(6) . . . . ? C36B_2 C31B_2 C37B_2 O32B_2 -20(7) . . . . ? C32B_2 C31B_2 C37B_2 O31B_2 -24(6) . . . . ? C36B_2 C31B_2 C37B_2 O31B_2 167(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31A_1 H31A_1 N11A_1 0.84 1.77 2.571(10) 158.8 . O31B_1 H31B_1 N21B_1 0.84 1.90 2.72(4) 167.5 1_466 O31A_2 H31A_2 N11A_2 0.84 1.75 2.591(10) 177.2 . O31B_2 H31B_2 N21B_2 0.84 1.83 2.66(5) 175.0 1_766 _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.737 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.101 data_4,4'-azpy:OH-I _database_code_depnum_ccdc_archive 'CCDC 906991' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-AzoPy 3-HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-I-F4-PhOH ; _chemical_name_common "4,4'-AzoPy 3-HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-I-F4-PhOH" _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C6 H F4 I O) ; _chemical_formula_sum 'C16 H9 F4 I N4 O' _chemical_formula_weight 476.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 '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 6.1515(5) _cell_length_b 9.8197(7) _cell_length_c 13.7443(10) _cell_angle_alpha 81.558(3) _cell_angle_beta 85.932(3) _cell_angle_gamma 78.342(3) _cell_volume 803.57(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7041 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 68.81 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 16.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1813 _exptl_absorpt_correction_T_max 0.5633 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11713 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 68.90 _reflns_number_total 2764 _reflns_number_gt 2604 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2764 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 N11 N 0.2493(5) 0.2299(3) 0.4821(2) 0.0284(7) Uani 1 1 d . . . C12 C 0.4327(6) 0.2858(4) 0.4668(3) 0.0290(8) Uani 1 1 d . . . H12 H 0.4406 0.3644 0.4984 0.035 Uiso 1 1 calc R . . C13 C 0.6116(6) 0.2330(4) 0.4065(3) 0.0277(8) Uani 1 1 d . . . H13 H 0.7399 0.2742 0.3971 0.033 Uiso 1 1 calc R . . C14 C 0.5982(6) 0.1194(4) 0.3605(3) 0.0244(7) Uani 1 1 d . . . N14 N 0.7887(5) 0.0685(3) 0.3001(2) 0.0277(7) Uani 1 1 d . . . C15 C 0.4094(6) 0.0601(4) 0.3757(3) 0.0271(8) Uani 1 1 d . . . H15 H 0.3974 -0.0186 0.3451 0.032 Uiso 1 1 calc R . . C16 C 0.2402(6) 0.1198(4) 0.4368(3) 0.0285(8) Uani 1 1 d . . . H16 H 0.1101 0.0804 0.4472 0.034 Uiso 1 1 calc R . . N21 N 1.2797(5) -0.1576(3) 0.0502(2) 0.0286(7) Uani 1 1 d . . . C22 C 1.0968(7) -0.2132(4) 0.0654(3) 0.0322(8) Uani 1 1 d . . . H22 H 1.0864 -0.2885 0.0309 0.039 Uiso 1 1 calc R . . C23 C 0.9212(6) -0.1662(4) 0.1292(3) 0.0307(8) Uani 1 1 d . . . H23 H 0.7934 -0.2080 0.1379 0.037 Uiso 1 1 calc R . . C24 C 0.9375(6) -0.0574(4) 0.1794(3) 0.0255(7) Uani 1 1 d . . . N24 N 0.7498(5) -0.0091(3) 0.2422(2) 0.0287(7) Uani 1 1 d . . . C25 C 1.1243(6) 0.0022(4) 0.1646(3) 0.0289(8) Uani 1 1 d . . . H25 H 1.1383 0.0777 0.1982 0.035 Uiso 1 1 calc R . . C26 C 1.2908(6) -0.0514(4) 0.0992(3) 0.0284(8) Uani 1 1 d . . . H26 H 1.4194 -0.0106 0.0887 0.034 Uiso 1 1 calc R . . C31 C -0.1787(6) 0.3604(4) 0.6561(3) 0.0256(7) Uani 1 1 d . . . O31 O -0.1160(4) 0.2688(3) 0.59237(19) 0.0332(6) Uani 1 1 d . . . H31 H 0.0095 0.2775 0.5669 0.040 Uiso 1 1 calc R . . C32 C -0.3758(6) 0.3560(4) 0.7129(3) 0.0261(8) Uani 1 1 d . . . F32 F -0.4956(3) 0.2599(2) 0.70107(16) 0.0322(5) Uani 1 1 d . . . C33 C -0.4498(6) 0.4466(4) 0.7805(3) 0.0260(7) Uani 1 1 d . . . F33 F -0.6408(3) 0.4346(2) 0.83189(16) 0.0317(5) Uani 1 1 d . . . C34 C -0.3321(6) 0.5474(4) 0.7975(3) 0.0250(7) Uani 1 1 d . . . I1 I -0.45160(4) 0.68106(2) 0.902714(15) 0.02822(11) Uani 1 1 d . . . C35 C -0.1384(6) 0.5524(4) 0.7416(3) 0.0267(8) Uani 1 1 d . . . F35 F -0.0159(4) 0.6498(2) 0.75150(16) 0.0334(5) Uani 1 1 d . . . C36 C -0.0647(6) 0.4637(4) 0.6734(3) 0.0274(8) Uani 1 1 d . . . F36 F 0.1252(3) 0.4751(2) 0.61837(17) 0.0343(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0288(16) 0.0275(16) 0.0287(15) -0.0094(13) 0.0053(13) -0.0036(13) C12 0.0300(19) 0.0259(19) 0.0327(19) -0.0123(16) 0.0011(16) -0.0038(16) C13 0.0299(19) 0.0261(19) 0.0295(18) -0.0102(15) 0.0022(15) -0.0076(16) C14 0.0227(17) 0.0241(18) 0.0260(17) -0.0052(15) 0.0018(14) -0.0030(14) N14 0.0299(16) 0.0257(16) 0.0291(15) -0.0120(13) 0.0037(13) -0.0053(13) C15 0.0310(19) 0.0234(18) 0.0283(17) -0.0101(15) 0.0011(15) -0.0049(15) C16 0.0271(18) 0.0282(19) 0.0314(18) -0.0083(16) 0.0023(15) -0.0065(15) N21 0.0300(16) 0.0248(16) 0.0302(16) -0.0081(13) 0.0066(13) -0.0028(13) C22 0.038(2) 0.0251(19) 0.035(2) -0.0133(16) 0.0039(17) -0.0050(17) C23 0.0272(18) 0.031(2) 0.0359(19) -0.0124(16) 0.0021(15) -0.0056(16) C24 0.0261(18) 0.0213(18) 0.0288(18) -0.0058(15) 0.0035(15) -0.0037(14) N24 0.0310(16) 0.0240(15) 0.0322(16) -0.0086(13) 0.0054(13) -0.0068(13) C25 0.0343(19) 0.0267(19) 0.0283(18) -0.0121(15) 0.0009(15) -0.0070(16) C26 0.0283(18) 0.0265(19) 0.0317(18) -0.0100(16) 0.0038(15) -0.0053(15) C31 0.0269(17) 0.0228(18) 0.0269(17) -0.0094(15) 0.0029(14) -0.0015(15) O31 0.0293(13) 0.0360(15) 0.0387(14) -0.0217(12) 0.0095(11) -0.0086(11) C32 0.0277(18) 0.0219(18) 0.0304(17) -0.0064(15) -0.0026(15) -0.0060(15) F32 0.0350(11) 0.0282(11) 0.0384(11) -0.0143(9) 0.0033(9) -0.0127(9) C33 0.0248(17) 0.0242(18) 0.0284(17) -0.0060(15) 0.0028(14) -0.0032(14) F33 0.0295(11) 0.0307(11) 0.0372(11) -0.0133(9) 0.0103(9) -0.0093(9) C34 0.0296(18) 0.0190(17) 0.0266(17) -0.0074(14) 0.0035(14) -0.0035(14) I1 0.03616(16) 0.02111(15) 0.02884(15) -0.00991(10) 0.00491(10) -0.00647(10) C35 0.0323(19) 0.0210(18) 0.0288(17) -0.0070(15) -0.0017(15) -0.0069(15) F35 0.0344(11) 0.0287(11) 0.0422(12) -0.0149(10) 0.0053(10) -0.0135(9) C36 0.0267(18) 0.0238(18) 0.0323(18) -0.0080(16) 0.0020(15) -0.0047(15) F36 0.0293(11) 0.0323(12) 0.0440(12) -0.0143(10) 0.0126(9) -0.0112(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 N11 C16 1.337(5) . ? N11 C12 1.342(5) . ? C12 C13 1.391(6) . ? C12 H12 0.9500 . ? C13 C14 1.379(5) . ? C13 H13 0.9500 . ? C14 C15 1.391(5) . ? C14 N14 1.435(5) . ? N14 N24 1.245(4) . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C26 1.337(5) . ? N21 C22 1.337(5) . ? C22 C23 1.390(6) . ? C22 H22 0.9500 . ? C23 C24 1.378(6) . ? C23 H23 0.9500 . ? C24 C25 1.382(5) . ? C24 N24 1.435(5) . ? C25 C26 1.387(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 O31 1.330(4) . ? C31 C32 1.399(5) . ? C31 C36 1.400(5) . ? O31 H31 0.8400 . ? C32 F32 1.343(4) . ? C32 C33 1.372(5) . ? C33 F33 1.344(4) . ? C33 C34 1.393(5) . ? C34 C35 1.377(5) . ? C34 I1 2.090(4) . ? I1 N21 2.960(3) 1_366 ? C35 F35 1.358(4) . ? C35 C36 1.365(5) . ? C36 F36 1.361(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 C16 N11 C12 118.1(3) . . ? N11 C12 C13 122.4(4) . . ? N11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C14 C13 C12 118.4(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 N14 115.9(3) . . ? C15 C14 N14 124.2(3) . . ? N24 N14 C14 113.2(3) . . ? C16 C15 C14 117.6(3) . . ? C16 C15 H15 121.2 . . ? C14 C15 H15 121.2 . . ? N11 C16 C15 123.6(3) . . ? N11 C16 H16 118.2 . . ? C15 C16 H16 118.2 . . ? C26 N21 C22 117.4(3) . . ? N21 C22 C23 123.3(4) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C24 C23 C22 118.1(4) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C23 C24 C25 119.7(4) . . ? C23 C24 N24 116.4(3) . . ? C25 C24 N24 123.8(3) . . ? N14 N24 C24 113.7(3) . . ? C24 C25 C26 118.0(3) . . ? C24 C25 H25 121.0 . . ? C26 C25 H25 121.0 . . ? N21 C26 C25 123.4(3) . . ? N21 C26 H26 118.3 . . ? C25 C26 H26 118.3 . . ? O31 C31 C32 118.8(3) . . ? O31 C31 C36 126.1(3) . . ? C32 C31 C36 115.1(3) . . ? C31 O31 H31 109.5 . . ? F32 C32 C33 119.1(3) . . ? F32 C32 C31 119.0(3) . . ? C33 C32 C31 121.9(3) . . ? F33 C33 C32 117.9(3) . . ? F33 C33 C34 120.1(3) . . ? C32 C33 C34 122.0(3) . . ? C35 C34 C33 116.2(3) . . ? C35 C34 I1 123.5(3) . . ? C33 C34 I1 120.3(3) . . ? C34 I1 N21 165.98(11) . 1_366 ? F35 C35 C36 117.6(3) . . ? F35 C35 C34 120.3(3) . . ? C36 C35 C34 122.1(3) . . ? F36 C36 C35 119.8(3) . . ? F36 C36 C31 117.6(3) . . ? C35 C36 C31 122.6(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 C16 N11 C12 C13 -0.3(5) . . . . ? N11 C12 C13 C14 0.3(6) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C12 C13 C14 N14 -179.3(3) . . . . ? C13 C14 N14 N24 -163.3(3) . . . . ? C15 C14 N14 N24 17.8(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? N14 C14 C15 C16 179.3(3) . . . . ? C12 N11 C16 C15 0.4(5) . . . . ? C14 C15 C16 N11 -0.4(5) . . . . ? C26 N21 C22 C23 -0.2(6) . . . . ? N21 C22 C23 C24 -0.3(6) . . . . ? C22 C23 C24 C25 0.6(6) . . . . ? C22 C23 C24 N24 178.1(3) . . . . ? C14 N14 N24 C24 178.3(3) . . . . ? C23 C24 N24 N14 166.4(3) . . . . ? C25 C24 N24 N14 -16.2(5) . . . . ? C23 C24 C25 C26 -0.4(5) . . . . ? N24 C24 C25 C26 -177.7(3) . . . . ? C22 N21 C26 C25 0.4(5) . . . . ? C24 C25 C26 N21 -0.1(6) . . . . ? O31 C31 C32 F32 -0.1(5) . . . . ? C36 C31 C32 F32 -179.9(3) . . . . ? O31 C31 C32 C33 179.6(3) . . . . ? C36 C31 C32 C33 -0.2(5) . . . . ? F32 C32 C33 F33 -0.2(5) . . . . ? C31 C32 C33 F33 -179.9(3) . . . . ? F32 C32 C33 C34 179.0(3) . . . . ? C31 C32 C33 C34 -0.7(5) . . . . ? F33 C33 C34 C35 -179.9(3) . . . . ? C32 C33 C34 C35 0.8(5) . . . . ? F33 C33 C34 I1 -0.1(4) . . . . ? C32 C33 C34 I1 -179.3(3) . . . . ? C35 C34 I1 N21 167.9(3) . . . 1_366 ? C33 C34 I1 N21 -12.0(6) . . . 1_366 ? C33 C34 C35 F35 178.3(3) . . . . ? I1 C34 C35 F35 -1.5(5) . . . . ? C33 C34 C35 C36 -0.1(5) . . . . ? I1 C34 C35 C36 -179.9(3) . . . . ? F35 C35 C36 F36 0.0(5) . . . . ? C34 C35 C36 F36 178.4(3) . . . . ? F35 C35 C36 C31 -179.3(3) . . . . ? C34 C35 C36 C31 -0.8(6) . . . . ? O31 C31 C36 F36 1.9(5) . . . . ? C32 C31 C36 F36 -178.3(3) . . . . ? O31 C31 C36 C35 -178.8(3) . . . . ? C32 C31 C36 C35 1.0(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 0.84 1.84 2.614(4) 152.3 . _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.462 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.103 data_4,4'-azpy:OH-Br _database_code_depnum_ccdc_archive 'CCDC 906992' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-AzoPy 4-HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-Br-F4-PhOH ; _chemical_name_common "4,4'-AzoPy 4-HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-Br-F4-PhOH" _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C6 H Br F4 O) ; _chemical_formula_sum 'C16 H9 Br F4 N4 O' _chemical_formula_weight 429.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _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 6.3706(3) _cell_length_b 9.5670(5) _cell_length_c 13.3289(7) _cell_angle_alpha 79.453(2) _cell_angle_beta 83.090(2) _cell_angle_gamma 79.4760(10) _cell_volume 782.03(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9904 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 32.61 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.823 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 2.687 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5804 _exptl_absorpt_correction_T_max 0.7464 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17166 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 32.57 _reflns_number_total 5315 _reflns_number_gt 4829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0450P)^2^+0.1500P] 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 5315 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 N11 N 0.26012(18) 0.26981(12) 0.51773(9) 0.0194(2) Uani 1 1 d . . . C12 C 0.0798(2) 0.21336(14) 0.53042(11) 0.0202(2) Uani 1 1 d . . . H12A H 0.0750 0.1351 0.4965 0.024 Uiso 1 1 calc R . . C13 C -0.1008(2) 0.26394(14) 0.59098(11) 0.0197(2) Uani 1 1 d . . . H13A H -0.2269 0.2218 0.5981 0.024 Uiso 1 1 calc R . . C14 C -0.0923(2) 0.37806(13) 0.64094(10) 0.0169(2) Uani 1 1 d . . . N14 N -0.28466(19) 0.42901(12) 0.70025(9) 0.0200(2) Uani 1 1 d . . . C15 C 0.0940(2) 0.43862(13) 0.62828(10) 0.0181(2) Uani 1 1 d . . . H15A H 0.1031 0.5174 0.6609 0.022 Uiso 1 1 calc R . . C16 C 0.2651(2) 0.38004(14) 0.56667(11) 0.0196(2) Uani 1 1 d . . . H16A H 0.3935 0.4198 0.5584 0.023 Uiso 1 1 calc R . . N21 N -0.7982(2) 0.65352(13) 0.95081(9) 0.0215(2) Uani 1 1 d . . . C22 C -0.6154(2) 0.70680(14) 0.94133(11) 0.0219(2) Uani 1 1 d . . . H22A H -0.6095 0.7814 0.9787 0.026 Uiso 1 1 calc R . . C23 C -0.4338(2) 0.65923(14) 0.88000(11) 0.0206(2) Uani 1 1 d . . . H23A H -0.3066 0.6995 0.8758 0.025 Uiso 1 1 calc R . . C24 C -0.4443(2) 0.55051(13) 0.82493(10) 0.0172(2) Uani 1 1 d . . . N24 N -0.25323(18) 0.50177(12) 0.76418(9) 0.0194(2) Uani 1 1 d . . . C25 C -0.6317(2) 0.49230(14) 0.83452(10) 0.0186(2) Uani 1 1 d . . . H25A H -0.6416 0.4168 0.7988 0.022 Uiso 1 1 calc R . . C26 C -0.8040(2) 0.54781(14) 0.89794(11) 0.0203(2) Uani 1 1 d . . . H26A H -0.9327 0.5089 0.9042 0.024 Uiso 1 1 calc R . . C31 C 0.6898(2) 0.13945(13) 0.33926(10) 0.0180(2) Uani 1 1 d . . . O31 O 0.62864(17) 0.23194(11) 0.40504(8) 0.0231(2) Uani 1 1 d . . . H31 H 0.506(4) 0.224(2) 0.4317(16) 0.028 Uiso 1 1 d . . . C32 C 0.5714(2) 0.03785(13) 0.32290(10) 0.0184(2) Uani 1 1 d . . . F32 F 0.38138(14) 0.02844(9) 0.37857(7) 0.02528(17) Uani 1 1 d . . . C33 C 0.6435(2) -0.05410(13) 0.25298(10) 0.0184(2) Uani 1 1 d . . . F33 F 0.52028(14) -0.14956(9) 0.24273(7) 0.02423(17) Uani 1 1 d . . . C34 C 0.8398(2) -0.05094(13) 0.19589(10) 0.0181(2) Uani 1 1 d . . . Br1 Br 0.94145(2) -0.175814(12) 0.100968(10) 0.02118(5) Uani 1 1 d . . . C35 C 0.9608(2) 0.04843(13) 0.21214(10) 0.0178(2) Uani 1 1 d . . . F35 F 1.15189(14) 0.05702(9) 0.15961(7) 0.02406(17) Uani 1 1 d . . . C36 C 0.8879(2) 0.14080(13) 0.28164(10) 0.0178(2) Uani 1 1 d . . . F36 F 1.01018(14) 0.23615(9) 0.29346(7) 0.02292(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 N11 0.0196(5) 0.0197(5) 0.0180(5) -0.0049(4) 0.0030(4) -0.0019(4) C12 0.0233(6) 0.0189(5) 0.0190(6) -0.0063(5) 0.0017(5) -0.0040(5) C13 0.0201(6) 0.0197(5) 0.0203(6) -0.0061(5) 0.0015(5) -0.0052(4) C14 0.0170(5) 0.0178(5) 0.0156(5) -0.0037(4) 0.0015(4) -0.0028(4) N14 0.0181(5) 0.0219(5) 0.0205(5) -0.0077(4) 0.0027(4) -0.0032(4) C15 0.0192(6) 0.0175(5) 0.0180(6) -0.0047(4) 0.0012(4) -0.0048(4) C16 0.0180(6) 0.0202(5) 0.0201(6) -0.0039(5) 0.0025(5) -0.0043(4) N21 0.0216(5) 0.0214(5) 0.0202(5) -0.0057(4) 0.0039(4) -0.0020(4) C22 0.0248(6) 0.0205(5) 0.0211(6) -0.0076(5) 0.0029(5) -0.0044(5) C23 0.0208(6) 0.0193(5) 0.0228(6) -0.0069(5) 0.0015(5) -0.0052(5) C24 0.0170(5) 0.0176(5) 0.0162(5) -0.0043(4) 0.0021(4) -0.0018(4) N24 0.0187(5) 0.0194(4) 0.0203(5) -0.0067(4) 0.0035(4) -0.0040(4) C25 0.0189(6) 0.0198(5) 0.0181(6) -0.0060(5) 0.0015(5) -0.0049(4) C26 0.0183(6) 0.0228(5) 0.0196(6) -0.0048(5) 0.0028(5) -0.0044(5) C31 0.0183(6) 0.0171(5) 0.0184(6) -0.0051(4) 0.0017(4) -0.0022(4) O31 0.0212(5) 0.0255(4) 0.0253(5) -0.0141(4) 0.0064(4) -0.0061(4) C32 0.0167(5) 0.0179(5) 0.0200(6) -0.0049(4) 0.0043(4) -0.0034(4) F32 0.0192(4) 0.0272(4) 0.0309(4) -0.0121(3) 0.0096(3) -0.0078(3) C33 0.0192(6) 0.0154(5) 0.0209(6) -0.0046(4) 0.0016(5) -0.0046(4) F33 0.0230(4) 0.0215(4) 0.0314(5) -0.0107(3) 0.0037(3) -0.0094(3) C34 0.0208(6) 0.0157(5) 0.0172(6) -0.0046(4) 0.0026(5) -0.0021(4) Br1 0.02616(8) 0.01767(7) 0.01973(7) -0.00727(5) 0.00506(5) -0.00407(5) C35 0.0169(5) 0.0172(5) 0.0179(6) -0.0033(4) 0.0044(4) -0.0031(4) F35 0.0197(4) 0.0267(4) 0.0264(4) -0.0093(3) 0.0088(3) -0.0074(3) C36 0.0188(6) 0.0168(5) 0.0184(6) -0.0042(4) 0.0016(4) -0.0051(4) F36 0.0226(4) 0.0226(4) 0.0264(4) -0.0090(3) 0.0032(3) -0.0096(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 N11 C12 1.3367(18) . ? N11 C16 1.3445(17) . ? C12 C13 1.3877(19) . ? C12 H12A 0.9500 . ? C13 C14 1.3910(18) . ? C13 H13A 0.9500 . ? C14 C15 1.3933(18) . ? C14 N14 1.4330(17) . ? N14 N24 1.2490(16) . ? C15 C16 1.3807(18) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? N21 C22 1.3378(19) . ? N21 C26 1.3421(18) . ? C22 C23 1.3895(19) . ? C22 H22A 0.9500 . ? C23 C24 1.3934(18) . ? C23 H23A 0.9500 . ? C24 C25 1.3900(18) . ? C24 N24 1.4310(17) . ? C25 C26 1.3891(19) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C31 O31 1.3340(16) . ? C31 C32 1.3953(17) . ? C31 C36 1.3972(18) . ? O31 H31 0.83(2) . ? C32 F32 1.3501(15) . ? C32 C33 1.3794(18) . ? C33 F33 1.3426(14) . ? C33 C34 1.3856(19) . ? C34 C35 1.3887(18) . ? C34 Br1 1.8764(13) . ? Br1 N21 2.9717(12) 1_744 ? C35 F35 1.3376(15) . ? C35 C36 1.3788(18) . ? C36 F36 1.3436(14) . ? 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 C12 N11 C16 117.92(12) . . ? N11 C12 C13 122.97(12) . . ? N11 C12 H12A 118.5 . . ? C13 C12 H12A 118.5 . . ? C12 C13 C14 118.20(12) . . ? C12 C13 H13A 120.9 . . ? C14 C13 H13A 120.9 . . ? C13 C14 C15 119.62(12) . . ? C13 C14 N14 116.11(11) . . ? C15 C14 N14 124.22(11) . . ? N24 N14 C14 113.02(11) . . ? C16 C15 C14 117.64(12) . . ? C16 C15 H15A 121.2 . . ? C14 C15 H15A 121.2 . . ? N11 C16 C15 123.64(12) . . ? N11 C16 H16A 118.2 . . ? C15 C16 H16A 118.2 . . ? C22 N21 C26 117.47(12) . . ? N21 C22 C23 123.71(12) . . ? N21 C22 H22A 118.1 . . ? C23 C22 H22A 118.1 . . ? C22 C23 C24 117.81(12) . . ? C22 C23 H23A 121.1 . . ? C24 C23 H23A 121.1 . . ? C25 C24 C23 119.49(12) . . ? C25 C24 N24 124.00(11) . . ? C23 C24 N24 116.46(11) . . ? N14 N24 C24 113.19(11) . . ? C26 C25 C24 118.00(12) . . ? C26 C25 H25A 121.0 . . ? C24 C25 H25A 121.0 . . ? N21 C26 C25 123.50(12) . . ? N21 C26 H26A 118.3 . . ? C25 C26 H26A 118.3 . . ? O31 C31 C32 125.12(12) . . ? O31 C31 C36 119.01(11) . . ? C32 C31 C36 115.87(12) . . ? C31 O31 H31 110.0(15) . . ? F32 C32 C33 119.22(11) . . ? F32 C32 C31 118.61(11) . . ? C33 C32 C31 122.16(12) . . ? F33 C33 C32 118.28(12) . . ? F33 C33 C34 120.36(11) . . ? C32 C33 C34 121.34(12) . . ? C33 C34 C35 117.22(11) . . ? C33 C34 Br1 121.98(10) . . ? C35 C34 Br1 120.80(10) . . ? C34 Br1 N21 165.95(5) . 1_744 ? F35 C35 C36 118.38(11) . . ? F35 C35 C34 120.26(11) . . ? C36 C35 C34 121.36(12) . . ? F36 C36 C35 118.95(12) . . ? F36 C36 C31 119.00(11) . . ? C35 C36 C31 122.04(12) . . ? 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 C16 N11 C12 C13 0.4(2) . . . . ? N11 C12 C13 C14 -0.3(2) . . . . ? C12 C13 C14 C15 0.59(19) . . . . ? C12 C13 C14 N14 178.34(11) . . . . ? C13 C14 N14 N24 161.66(12) . . . . ? C15 C14 N14 N24 -20.71(18) . . . . ? C13 C14 C15 C16 -0.83(19) . . . . ? N14 C14 C15 C16 -178.38(12) . . . . ? C12 N11 C16 C15 -0.6(2) . . . . ? C14 C15 C16 N11 0.9(2) . . . . ? C26 N21 C22 C23 0.2(2) . . . . ? N21 C22 C23 C24 0.5(2) . . . . ? C22 C23 C24 C25 -1.19(19) . . . . ? C22 C23 C24 N24 -178.73(12) . . . . ? C14 N14 N24 C24 -178.86(10) . . . . ? C25 C24 N24 N14 17.44(18) . . . . ? C23 C24 N24 N14 -165.15(12) . . . . ? C23 C24 C25 C26 1.23(19) . . . . ? N24 C24 C25 C26 178.57(12) . . . . ? C22 N21 C26 C25 -0.2(2) . . . . ? C24 C25 C26 N21 -0.5(2) . . . . ? O31 C31 C32 F32 -1.4(2) . . . . ? C36 C31 C32 F32 178.06(11) . . . . ? O31 C31 C32 C33 179.52(13) . . . . ? C36 C31 C32 C33 -1.0(2) . . . . ? F32 C32 C33 F33 0.32(19) . . . . ? C31 C32 C33 F33 179.38(12) . . . . ? F32 C32 C33 C34 -178.40(12) . . . . ? C31 C32 C33 C34 0.7(2) . . . . ? F33 C33 C34 C35 -178.58(11) . . . . ? C32 C33 C34 C35 0.1(2) . . . . ? F33 C33 C34 Br1 0.95(18) . . . . ? C32 C33 C34 Br1 179.64(10) . . . . ? C33 C34 Br1 N21 -168.81(13) . . . 1_744 ? C35 C34 Br1 N21 10.7(3) . . . 1_744 ? C33 C34 C35 F35 179.94(11) . . . . ? Br1 C34 C35 F35 0.41(18) . . . . ? C33 C34 C35 C36 -0.5(2) . . . . ? Br1 C34 C35 C36 179.98(10) . . . . ? F35 C35 C36 F36 0.44(18) . . . . ? C34 C35 C36 F36 -179.15(12) . . . . ? F35 C35 C36 C31 179.67(12) . . . . ? C34 C35 C36 C31 0.1(2) . . . . ? O31 C31 C36 F36 -0.62(19) . . . . ? C32 C31 C36 F36 179.88(11) . . . . ? O31 C31 C36 C35 -179.86(12) . . . . ? C32 C31 C36 C35 0.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 0.83(2) 1.86(2) 2.6342(16) 155(2) . _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.906 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.078 data_4,4'-azpy:Ox-I _database_code_depnum_ccdc_archive 'CCDC 906993' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-AzoPy 8HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-I-F4-PhCHO oxime ; _chemical_name_common ;4,4'-AzoPy 8HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-I-F4-PhCHO oxime ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H2 F4 I N O) ; _chemical_formula_sum 'C17 H10 F4 I N5 O' _chemical_formula_weight 503.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 17.6282(7) _cell_length_b 6.3167(3) _cell_length_c 31.7318(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.518(2) _cell_angle_gamma 90.00 _cell_volume 3510.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9920 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 32.64 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 1.884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6401 _exptl_absorpt_correction_T_max 0.9284 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27187 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 32.57 _reflns_number_total 6206 _reflns_number_gt 5308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0250P)^2^+4.0000P] 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 6206 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0575 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 N11 N 0.69588(8) 0.5108(2) 0.21526(5) 0.0237(3) Uani 1 1 d . . . C12 C 0.74795(10) 0.5603(3) 0.18921(6) 0.0229(3) Uani 1 1 d . . . H12 H 0.7685 0.6995 0.1906 0.027 Uiso 1 1 calc R . . C13 C 0.77328(9) 0.4210(2) 0.16066(5) 0.0213(3) Uani 1 1 d . . . H13 H 0.8100 0.4628 0.1426 0.026 Uiso 1 1 calc R . . C14 C 0.74367(8) 0.2177(3) 0.15904(5) 0.0195(3) Uani 1 1 d . . . N14 N 0.76434(8) 0.0582(2) 0.13054(5) 0.0217(3) Uani 1 1 d . . . C15 C 0.69153(9) 0.1602(3) 0.18647(5) 0.0228(3) Uani 1 1 d . . . H15 H 0.6717 0.0204 0.1865 0.027 Uiso 1 1 calc R . . C16 C 0.66910(9) 0.3121(3) 0.21388(6) 0.0240(3) Uani 1 1 d . . . H16 H 0.6330 0.2738 0.2326 0.029 Uiso 1 1 calc R . . N21 N 0.86401(8) -0.3125(2) 0.01388(5) 0.0253(3) Uani 1 1 d . . . C22 C 0.81156(10) -0.3636(3) 0.03939(6) 0.0247(3) Uani 1 1 d . . . H22 H 0.7895 -0.5009 0.0368 0.030 Uiso 1 1 calc R . . C23 C 0.78768(9) -0.2283(3) 0.06929(5) 0.0226(3) Uani 1 1 d . . . H23 H 0.7499 -0.2703 0.0867 0.027 Uiso 1 1 calc R . . C24 C 0.82058(9) -0.0284(3) 0.07322(5) 0.0204(3) Uani 1 1 d . . . N24 N 0.80119(8) 0.1290(2) 0.10237(5) 0.0228(3) Uani 1 1 d . . . C25 C 0.87433(9) 0.0291(3) 0.04645(6) 0.0236(3) Uani 1 1 d . . . H25 H 0.8967 0.1661 0.0480 0.028 Uiso 1 1 calc R . . C26 C 0.89419(10) -0.1191(3) 0.01757(6) 0.0253(3) Uani 1 1 d . . . H26 H 0.9313 -0.0810 -0.0006 0.030 Uiso 1 1 calc R . . C31 C 0.50959(9) 0.5161(3) 0.33929(5) 0.0194(3) Uani 1 1 d . . . C32 C 0.53901(8) 0.3158(3) 0.34950(5) 0.0206(3) Uani 1 1 d . . . F32 F 0.59527(6) 0.23616(16) 0.32932(4) 0.0284(2) Uani 1 1 d . . . C33 C 0.51264(8) 0.1922(2) 0.38045(5) 0.0198(3) Uani 1 1 d . . . F33 F 0.54624(5) 0.00380(16) 0.38893(3) 0.0250(2) Uani 1 1 d . . . C34 C 0.45447(8) 0.2589(2) 0.40321(5) 0.0195(3) Uani 1 1 d . . . I1 I 0.414643(5) 0.072635(16) 0.450479(3) 0.02099(4) Uani 1 1 d . . . C35 C 0.42431(9) 0.4567(3) 0.39310(5) 0.0201(3) Uani 1 1 d . . . F35 F 0.36721(6) 0.53166(16) 0.41355(3) 0.0254(2) Uani 1 1 d . . . C36 C 0.45076(9) 0.5802(2) 0.36216(5) 0.0198(3) Uani 1 1 d . . . F36 F 0.41784(5) 0.77011(15) 0.35378(3) 0.0239(2) Uani 1 1 d . . . C37 C 0.53701(9) 0.6589(3) 0.30805(5) 0.0221(3) Uani 1 1 d . . . H37A H 0.5155 0.7964 0.3042 0.027 Uiso 1 1 calc R . . N37 N 0.58941(8) 0.6011(2) 0.28597(5) 0.0226(3) Uani 1 1 d . . . O37 O 0.60776(7) 0.7608(2) 0.25895(4) 0.0257(2) Uani 1 1 d . . . H37 H 0.6380(13) 0.699(4) 0.2455(7) 0.031 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0252(6) 0.0249(7) 0.0215(7) -0.0007(6) 0.0049(5) -0.0006(5) C12 0.0259(7) 0.0199(7) 0.0233(8) 0.0003(6) 0.0043(6) -0.0016(6) C13 0.0212(7) 0.0221(7) 0.0212(7) 0.0007(6) 0.0046(6) -0.0026(5) C14 0.0202(6) 0.0209(7) 0.0172(7) 0.0000(6) 0.0014(5) -0.0009(5) N14 0.0228(6) 0.0226(7) 0.0200(6) -0.0004(5) 0.0036(5) -0.0020(5) C15 0.0247(7) 0.0217(8) 0.0222(7) 0.0016(6) 0.0036(6) -0.0042(6) C16 0.0252(7) 0.0268(8) 0.0210(7) 0.0013(7) 0.0064(6) -0.0022(6) N21 0.0271(6) 0.0274(7) 0.0217(7) -0.0014(6) 0.0038(5) 0.0037(6) C22 0.0274(7) 0.0218(7) 0.0250(8) -0.0018(7) 0.0034(6) -0.0006(6) C23 0.0233(7) 0.0226(7) 0.0225(8) 0.0004(6) 0.0046(6) -0.0021(6) C24 0.0203(6) 0.0213(7) 0.0197(7) 0.0004(6) 0.0030(6) 0.0005(5) N24 0.0247(6) 0.0230(6) 0.0215(7) -0.0003(6) 0.0059(5) -0.0017(5) C25 0.0249(7) 0.0236(8) 0.0232(8) 0.0012(7) 0.0062(6) -0.0016(6) C26 0.0252(7) 0.0296(8) 0.0220(8) 0.0016(7) 0.0063(6) 0.0010(6) C31 0.0196(6) 0.0197(7) 0.0188(7) -0.0019(6) 0.0016(5) 0.0020(5) C32 0.0176(6) 0.0228(7) 0.0221(7) -0.0020(6) 0.0048(6) 0.0038(5) F32 0.0277(5) 0.0256(5) 0.0346(6) 0.0040(4) 0.0150(4) 0.0106(4) C33 0.0184(6) 0.0179(7) 0.0229(7) -0.0008(6) 0.0012(6) 0.0032(5) F33 0.0243(4) 0.0187(4) 0.0325(6) 0.0026(4) 0.0054(4) 0.0067(4) C34 0.0186(6) 0.0206(7) 0.0193(7) -0.0008(6) 0.0019(5) 0.0003(5) I1 0.02142(5) 0.02173(6) 0.01999(5) -0.00010(4) 0.00306(4) -0.00063(3) C35 0.0176(6) 0.0228(7) 0.0203(7) -0.0045(6) 0.0034(5) 0.0029(5) F35 0.0231(4) 0.0275(5) 0.0271(5) -0.0024(4) 0.0093(4) 0.0068(4) C36 0.0196(6) 0.0177(7) 0.0217(7) -0.0022(6) 0.0000(6) 0.0042(5) F36 0.0264(4) 0.0188(4) 0.0267(5) 0.0011(4) 0.0040(4) 0.0082(4) C37 0.0250(7) 0.0201(7) 0.0212(7) -0.0007(6) 0.0025(6) 0.0028(6) N37 0.0248(6) 0.0226(7) 0.0207(6) 0.0017(5) 0.0042(5) -0.0007(5) O37 0.0316(6) 0.0237(6) 0.0231(6) 0.0030(5) 0.0080(5) 0.0004(5) _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 N11 C16 1.340(2) . ? N11 C12 1.340(2) . ? C12 C13 1.373(2) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 C15 1.384(2) . ? C14 N14 1.428(2) . ? N14 N24 1.2462(19) . ? C15 C16 1.383(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C26 1.332(2) . ? N21 C22 1.336(2) . ? C22 C23 1.378(2) . ? C22 H22 0.9500 . ? C23 C24 1.389(2) . ? C23 H23 0.9500 . ? C24 C25 1.391(2) . ? C24 N24 1.425(2) . ? C25 C26 1.383(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.392(2) . ? C31 C32 1.392(2) . ? C31 C37 1.462(2) . ? C32 F32 1.3382(17) . ? C32 C33 1.376(2) . ? C33 F33 1.3430(18) . ? C33 C34 1.385(2) . ? C34 C35 1.381(2) . ? C34 I1 2.0896(16) . ? I1 N21 2.8200(15) 8_446 ? C35 F35 1.3443(17) . ? C35 C36 1.376(2) . ? C36 F36 1.3462(17) . ? C37 N37 1.275(2) . ? C37 H37A 0.9500 . ? N37 O37 1.3863(18) . ? O37 H37 0.82(2) . ? 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 C16 N11 C12 117.51(15) . . ? N11 C12 C13 123.65(15) . . ? N11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C12 C13 C14 117.98(15) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C15 C14 C13 119.61(15) . . ? C15 C14 N14 116.65(14) . . ? C13 C14 N14 123.73(14) . . ? N24 N14 C14 113.11(14) . . ? C16 C15 C14 118.13(15) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? N11 C16 C15 123.07(15) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C26 N21 C22 117.74(15) . . ? N21 C22 C23 123.62(16) . . ? N21 C22 H22 118.2 . . ? C23 C22 H22 118.2 . . ? C22 C23 C24 117.95(15) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? C23 C24 C25 119.29(15) . . ? C23 C24 N24 124.30(14) . . ? C25 C24 N24 116.38(15) . . ? N14 N24 C24 113.47(14) . . ? C26 C25 C24 117.99(16) . . ? C26 C25 H25 121.0 . . ? C24 C25 H25 121.0 . . ? N21 C26 C25 123.40(16) . . ? N21 C26 H26 118.3 . . ? C25 C26 H26 118.3 . . ? C36 C31 C32 115.01(14) . . ? C36 C31 C37 119.85(15) . . ? C32 C31 C37 125.12(14) . . ? F32 C32 C33 117.21(14) . . ? F32 C32 C31 120.47(14) . . ? C33 C32 C31 122.32(14) . . ? F33 C33 C32 117.94(13) . . ? F33 C33 C34 120.05(14) . . ? C32 C33 C34 121.99(14) . . ? C35 C34 C33 116.24(15) . . ? C35 C34 I1 121.62(11) . . ? C33 C34 I1 122.13(12) . . ? C34 I1 N21 178.38(5) . 8_446 ? F35 C35 C36 118.52(14) . . ? F35 C35 C34 119.75(14) . . ? C36 C35 C34 121.73(14) . . ? F36 C36 C35 118.22(14) . . ? F36 C36 C31 119.07(15) . . ? C35 C36 C31 122.70(14) . . ? N37 C37 C31 120.80(15) . . ? N37 C37 H37A 119.6 . . ? C31 C37 H37A 119.6 . . ? C37 N37 O37 111.47(14) . . ? N37 O37 H37 100.7(16) . . ? 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 C16 N11 C12 C13 2.0(3) . . . . ? N11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 -1.4(2) . . . . ? C12 C13 C14 N14 179.24(16) . . . . ? C15 C14 N14 N24 168.89(15) . . . . ? C13 C14 N14 N24 -11.8(2) . . . . ? C13 C14 C15 C16 1.9(2) . . . . ? N14 C14 C15 C16 -178.71(15) . . . . ? C12 N11 C16 C15 -1.4(3) . . . . ? C14 C15 C16 N11 -0.5(3) . . . . ? C26 N21 C22 C23 -0.5(3) . . . . ? N21 C22 C23 C24 -0.5(3) . . . . ? C22 C23 C24 C25 1.6(2) . . . . ? C22 C23 C24 N24 179.37(16) . . . . ? C14 N14 N24 C24 -178.68(13) . . . . ? C23 C24 N24 N14 14.8(2) . . . . ? C25 C24 N24 N14 -167.34(15) . . . . ? C23 C24 C25 C26 -1.7(3) . . . . ? N24 C24 C25 C26 -179.60(15) . . . . ? C22 N21 C26 C25 0.4(3) . . . . ? C24 C25 C26 N21 0.7(3) . . . . ? C36 C31 C32 F32 179.35(15) . . . . ? C37 C31 C32 F32 -2.2(3) . . . . ? C36 C31 C32 C33 -1.1(2) . . . . ? C37 C31 C32 C33 177.37(16) . . . . ? F32 C32 C33 F33 1.6(2) . . . . ? C31 C32 C33 F33 -177.97(15) . . . . ? F32 C32 C33 C34 -179.84(15) . . . . ? C31 C32 C33 C34 0.6(3) . . . . ? F33 C33 C34 C35 178.57(14) . . . . ? C32 C33 C34 C35 0.0(2) . . . . ? F33 C33 C34 I1 -1.1(2) . . . . ? C32 C33 C34 I1 -179.65(12) . . . . ? C35 C34 I1 N21 -178(100) . . . 8_446 ? C33 C34 I1 N21 2(2) . . . 8_446 ? C33 C34 C35 F35 179.41(14) . . . . ? I1 C34 C35 F35 -0.9(2) . . . . ? C33 C34 C35 C36 -0.1(2) . . . . ? I1 C34 C35 C36 179.60(12) . . . . ? F35 C35 C36 F36 -0.3(2) . . . . ? C34 C35 C36 F36 179.24(14) . . . . ? F35 C35 C36 C31 -179.99(15) . . . . ? C34 C35 C36 C31 -0.5(3) . . . . ? C32 C31 C36 F36 -178.68(14) . . . . ? C37 C31 C36 F36 2.8(2) . . . . ? C32 C31 C36 C35 1.0(2) . . . . ? C37 C31 C36 C35 -177.51(16) . . . . ? C36 C31 C37 N37 -178.10(16) . . . . ? C32 C31 C37 N37 3.5(3) . . . . ? C31 C37 N37 O37 -178.95(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O37 H37 N11 0.82(2) 1.90(2) 2.7052(19) 169(2) . _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 32.57 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.825 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.087 data_4,4'-azpy:Ox-Br _database_code_depnum_ccdc_archive 'CCDC 906994' #TrackingRef 'all cif new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'AzoPy 5-HBXB (4-pyridyl)-N=N-(4-pyridyl), (4-Br-F4-PhCHO oxime)2 ; _chemical_name_common ;4,4'AzoPy 5-HBXB (4-pyridyl)-N=N-(4-pyridyl), (4-Br-F4-PhCHO oxime)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C7 H2 Br F4 N O)2 ; _chemical_formula_sum 'C24 H12 Br2 F8 N6 O2' _chemical_formula_weight 728.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2846(10) _cell_length_b 4.6215(5) _cell_length_c 27.841(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.246(6) _cell_angle_gamma 90.00 _cell_volume 1309.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2128 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 68.33 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 4.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5662 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7830 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 68.72 _reflns_number_total 2257 _reflns_number_gt 1721 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.1000P)^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 2257 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1586 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.50494(5) 0.13770(13) 0.137433(17) 0.0524(3) Uani 1 1 d . . . N11 N 0.6641(4) 0.8666(9) 0.46679(14) 0.0442(10) Uani 1 1 d . . . C12 C 0.7509(5) 0.9426(12) 0.43720(17) 0.0451(12) Uani 1 1 d . . . H12 H 0.7418 0.8592 0.4057 0.054 Uiso 1 1 calc R . . C13 C 0.8514(5) 1.1328(11) 0.44993(17) 0.0438(12) Uani 1 1 d . . . H13 H 0.9113 1.1779 0.4280 0.053 Uiso 1 1 calc R . . C14 C 0.8643(5) 1.2598(12) 0.49595(17) 0.0420(11) Uani 1 1 d . . . N14 N 0.9650(4) 1.4566(10) 0.51527(14) 0.0442(10) Uani 1 1 d . . . C15 C 0.7743(5) 1.1851(12) 0.52637(18) 0.0475(13) Uani 1 1 d . . . H15 H 0.7796 1.2682 0.5578 0.057 Uiso 1 1 calc R . . C16 C 0.6766(5) 0.9880(13) 0.51032(18) 0.0499(13) Uani 1 1 d . . . H16 H 0.6156 0.9372 0.5315 0.060 Uiso 1 1 calc R . . C21 C 0.4924(5) 0.2229(11) 0.30502(17) 0.0404(11) Uani 1 1 d . . . C22 C 0.5766(5) 0.3904(11) 0.28136(19) 0.0440(12) Uani 1 1 d . . . F22 F 0.6571(3) 0.5866(7) 0.30617(10) 0.0488(7) Uani 1 1 d . . . C23 C 0.5818(5) 0.3655(11) 0.23243(18) 0.0431(12) Uani 1 1 d . . . F23 F 0.6626(3) 0.5397(7) 0.21208(10) 0.0497(7) Uani 1 1 d . . . C24 C 0.5030(5) 0.1690(11) 0.20440(17) 0.0411(12) Uani 1 1 d . . . C25 C 0.4207(5) -0.0029(12) 0.22705(18) 0.0431(11) Uani 1 1 d . . . F25 F 0.3418(3) -0.1988(7) 0.20115(10) 0.0506(8) Uani 1 1 d . . . C26 C 0.4158(5) 0.0243(11) 0.27594(18) 0.0403(11) Uani 1 1 d . . . F26 F 0.3347(3) -0.1523(6) 0.29619(11) 0.0472(7) Uani 1 1 d . . . C27 C 0.4755(5) 0.2515(14) 0.35599(17) 0.0457(12) Uani 1 1 d . . . H27A H 0.4238 0.1135 0.3700 0.055 Uiso 1 1 calc R . . N27 N 0.5288(4) 0.4578(10) 0.38200(14) 0.0440(10) Uani 1 1 d . . . O27 O 0.4957(4) 0.4495(9) 0.42878(12) 0.0537(10) Uani 1 1 d . . . H27 H 0.538(6) 0.615(13) 0.443(2) 0.064 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0652(4) 0.0672(5) 0.0241(3) -0.0016(2) 0.0048(2) 0.0030(3) N11 0.050(2) 0.058(3) 0.024(2) 0.0011(17) 0.0018(16) -0.002(2) C12 0.054(3) 0.054(3) 0.028(2) 0.002(2) 0.007(2) -0.004(2) C13 0.051(3) 0.058(3) 0.023(2) 0.005(2) 0.007(2) 0.002(2) C14 0.052(3) 0.044(3) 0.030(2) 0.002(2) 0.004(2) 0.001(2) N14 0.052(2) 0.054(3) 0.027(2) 0.0004(18) 0.0063(16) -0.003(2) C15 0.055(3) 0.061(4) 0.027(3) -0.003(2) 0.007(2) -0.006(3) C16 0.054(3) 0.070(4) 0.026(2) -0.002(2) 0.007(2) -0.008(3) C21 0.049(3) 0.045(3) 0.027(2) 0.000(2) 0.002(2) 0.001(2) C22 0.046(3) 0.047(3) 0.038(3) -0.003(2) 0.001(2) 0.000(2) F22 0.0569(17) 0.0566(19) 0.0326(15) -0.0057(13) 0.0057(12) -0.0115(14) C23 0.044(3) 0.048(3) 0.037(3) 0.003(2) 0.005(2) 0.004(2) F23 0.0543(17) 0.0587(19) 0.0373(16) 0.0010(13) 0.0105(13) -0.0043(14) C24 0.050(3) 0.053(3) 0.021(2) 0.000(2) 0.0048(19) 0.007(2) C25 0.047(3) 0.045(3) 0.034(3) -0.005(2) -0.004(2) 0.000(2) F25 0.0587(17) 0.0568(19) 0.0340(16) -0.0089(13) -0.0010(13) -0.0042(14) C26 0.044(3) 0.040(3) 0.036(3) 0.003(2) 0.005(2) -0.001(2) F26 0.0557(17) 0.0492(18) 0.0366(15) -0.0018(12) 0.0062(12) -0.0057(13) C27 0.053(3) 0.051(3) 0.034(3) 0.001(2) 0.007(2) -0.008(3) N27 0.055(2) 0.050(3) 0.027(2) -0.0025(19) 0.0067(17) -0.003(2) O27 0.070(2) 0.064(3) 0.0281(18) -0.0052(17) 0.0127(16) -0.016(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 C24 1.873(5) . ? Br1 N14 3.395(4) 4_575 ? N11 C16 1.325(7) . ? N11 C12 1.345(6) . ? C12 C13 1.364(7) . ? C12 H12 0.9500 . ? C13 C14 1.398(7) . ? C13 H13 0.9500 . ? C14 C15 1.385(7) . ? C14 N14 1.425(7) . ? N14 N14 1.256(8) 3_786 ? C15 C16 1.382(8) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.392(7) . ? C21 C22 1.395(7) . ? C21 C27 1.460(6) . ? C22 F22 1.349(6) . ? C22 C23 1.376(7) . ? C23 F23 1.339(6) . ? C23 C24 1.382(7) . ? C24 C25 1.378(7) . ? C25 F25 1.352(6) . ? C25 C26 1.375(7) . ? C26 F26 1.347(6) . ? C27 N27 1.273(8) . ? C27 H27A 0.9500 . ? N27 O27 1.393(5) . ? O27 H27 0.94(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 C24 Br1 N14 171.94(17) . 4_575 ? C16 N11 C12 117.6(5) . . ? N11 C12 C13 123.6(5) . . ? N11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C12 C13 C14 118.5(4) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 118.2(5) . . ? C15 C14 N14 116.2(4) . . ? C13 C14 N14 125.6(4) . . ? N14 N14 C14 113.9(5) 3_786 . ? C16 C15 C14 119.0(5) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N11 C16 C15 123.1(5) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C26 C21 C22 115.4(4) . . ? C26 C21 C27 119.2(4) . . ? C22 C21 C27 125.2(5) . . ? F22 C22 C23 117.1(4) . . ? F22 C22 C21 120.5(4) . . ? C23 C22 C21 122.4(5) . . ? F23 C23 C22 118.9(4) . . ? F23 C23 C24 120.3(4) . . ? C22 C23 C24 120.7(5) . . ? C25 C24 C23 118.0(4) . . ? C25 C24 Br1 120.4(4) . . ? C23 C24 Br1 121.6(4) . . ? F25 C25 C26 119.0(4) . . ? F25 C25 C24 120.2(4) . . ? C26 C25 C24 120.8(5) . . ? F26 C26 C25 118.1(4) . . ? F26 C26 C21 119.3(4) . . ? C25 C26 C21 122.6(4) . . ? N27 C27 C21 121.3(5) . . ? N27 C27 H27A 119.4 . . ? C21 C27 H27A 119.4 . . ? C27 N27 O27 111.6(4) . . ? N27 O27 H27 103(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 C16 N11 C12 C13 1.1(8) . . . . ? N11 C12 C13 C14 -1.0(8) . . . . ? C12 C13 C14 C15 0.2(8) . . . . ? C12 C13 C14 N14 178.4(5) . . . . ? C15 C14 N14 N14 -172.3(5) . . . 3_786 ? C13 C14 N14 N14 9.4(9) . . . 3_786 ? C13 C14 C15 C16 0.5(8) . . . . ? N14 C14 C15 C16 -178.0(5) . . . . ? C12 N11 C16 C15 -0.4(8) . . . . ? C14 C15 C16 N11 -0.4(9) . . . . ? C26 C21 C22 F22 -178.9(4) . . . . ? C27 C21 C22 F22 4.2(8) . . . . ? C26 C21 C22 C23 1.3(8) . . . . ? C27 C21 C22 C23 -175.7(5) . . . . ? F22 C22 C23 F23 -1.7(7) . . . . ? C21 C22 C23 F23 178.1(4) . . . . ? F22 C22 C23 C24 179.8(4) . . . . ? C21 C22 C23 C24 -0.4(8) . . . . ? F23 C23 C24 C25 -179.3(4) . . . . ? C22 C23 C24 C25 -0.8(7) . . . . ? F23 C23 C24 Br1 -0.1(7) . . . . ? C22 C23 C24 Br1 178.4(4) . . . . ? N14 Br1 C24 C25 24.0(15) 4_575 . . . ? N14 Br1 C24 C23 -155.2(10) 4_575 . . . ? C23 C24 C25 F25 -179.9(4) . . . . ? Br1 C24 C25 F25 0.9(7) . . . . ? C23 C24 C25 C26 1.1(8) . . . . ? Br1 C24 C25 C26 -178.1(4) . . . . ? F25 C25 C26 F26 1.8(7) . . . . ? C24 C25 C26 F26 -179.2(4) . . . . ? F25 C25 C26 C21 -179.2(4) . . . . ? C24 C25 C26 C21 -0.1(8) . . . . ? C22 C21 C26 F26 178.0(4) . . . . ? C27 C21 C26 F26 -4.9(7) . . . . ? C22 C21 C26 C25 -1.0(7) . . . . ? C27 C21 C26 C25 176.1(5) . . . . ? C26 C21 C27 N27 -169.5(5) . . . . ? C22 C21 C27 N27 7.3(8) . . . . ? C21 C27 N27 O27 177.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O27 H27 N11 0.94(6) 1.79(6) 2.704(6) 162(6) . _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 1.198 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.153 #END