# 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_k1139 _database_code_depnum_ccdc_archive 'CCDC 906274' #TrackingRef '2b m-ClPhO-BsubPc k1139.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-Chlorophenolato)(subphthalocyaninato)boron ; _chemical_name_common ; m-ClPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B Cl N6 O' _chemical_formula_sum 'C30 H16 B Cl N6 O' _chemical_formula_weight 522.75 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.6086(7) _cell_length_b 21.0572(7) _cell_length_c 11.4521(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.680(2) _cell_angle_gamma 90.00 _cell_volume 2360.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 11708 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.202 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 15224 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.1126 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5309 _reflns_number_gt 2822 _reflns_threshold_expression I.2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0663P)^2^+0.2393P] 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 5309 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1475 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.99135(9) 0.34475(3) 0.84524(8) 0.0398(3) Uani 1 1 d . . . O1 O 0.7349(2) 0.13642(9) 0.74904(18) 0.0307(5) Uani 1 1 d . . . N1 N 0.5019(2) 0.09872(10) 0.6732(2) 0.0253(6) Uani 1 1 d . . . N2 N 0.5313(2) -0.01093(10) 0.7267(2) 0.0280(6) Uani 1 1 d . . . N3 N 0.6454(3) 0.06815(10) 0.8789(2) 0.0270(6) Uani 1 1 d . . . N4 N 0.6692(3) 0.13619(10) 1.0513(2) 0.0286(6) Uani 1 1 d . . . N5 N 0.5701(3) 0.17375(10) 0.8393(2) 0.0267(6) Uani 1 1 d . . . N6 N 0.3816(2) 0.19723(10) 0.6469(2) 0.0280(6) Uani 1 1 d . . . C1 C 0.3977(3) 0.13890(12) 0.6052(3) 0.0271(7) Uani 1 1 d . . . C2 C 0.3014(3) 0.09979(12) 0.5046(3) 0.0275(7) Uani 1 1 d . . . C3 C 0.1815(3) 0.11434(13) 0.4033(3) 0.0313(7) Uani 1 1 d . . . H3A H 0.1497 0.1569 0.3881 0.038 Uiso 1 1 calc R . . C4 C 0.1089(3) 0.06571(13) 0.3245(3) 0.0360(8) Uani 1 1 d . . . H4A H 0.0271 0.0750 0.2541 0.043 Uiso 1 1 calc R . . C5 C 0.1556(3) 0.00285(14) 0.3483(3) 0.0345(8) Uani 1 1 d . . . H5A H 0.1049 -0.0298 0.2930 0.041 Uiso 1 1 calc R . . C6 C 0.2734(3) -0.01267(13) 0.4501(3) 0.0287(7) Uani 1 1 d . . . H6A H 0.3030 -0.0555 0.4661 0.034 Uiso 1 1 calc R . . C7 C 0.3478(3) 0.03607(12) 0.5287(3) 0.0256(7) Uani 1 1 d . . . C8 C 0.4707(3) 0.03606(12) 0.6440(3) 0.0260(7) Uani 1 1 d . . . C9 C 0.6126(3) 0.00613(12) 0.8456(3) 0.0274(7) Uani 1 1 d . . . C10 C 0.6572(3) -0.02887(12) 0.9644(3) 0.0283(7) Uani 1 1 d . . . C11 C 0.6600(3) -0.09347(12) 0.9917(3) 0.0310(7) Uani 1 1 d . . . H11A H 0.6263 -0.1241 0.9260 0.037 Uiso 1 1 calc R . . C12 C 0.7132(3) -0.11154(14) 1.1172(3) 0.0354(8) Uani 1 1 d . . . H12A H 0.7192 -0.1555 1.1373 0.042 Uiso 1 1 calc R . . C13 C 0.7588(3) -0.06722(13) 1.2157(3) 0.0338(8) Uani 1 1 d . . . H13A H 0.7968 -0.0816 1.3009 0.041 Uiso 1 1 calc R . . C14 C 0.7491(3) -0.00268(13) 1.1905(3) 0.0316(7) Uani 1 1 d . . . H14A H 0.7744 0.0276 1.2571 0.038 Uiso 1 1 calc R . . C15 C 0.7010(3) 0.01643(12) 1.0639(3) 0.0262(7) Uani 1 1 d . . . C16 C 0.6805(3) 0.07868(12) 1.0054(3) 0.0266(7) Uani 1 1 d . . . C17 C 0.6055(3) 0.18175(12) 0.9663(3) 0.0259(7) Uani 1 1 d . . . C18 C 0.5347(3) 0.23867(12) 0.9798(3) 0.0265(7) Uani 1 1 d . . . C19 C 0.5350(3) 0.27185(12) 1.0851(3) 0.0301(7) Uani 1 1 d . . . H19A H 0.5914 0.2589 1.1684 0.036 Uiso 1 1 calc R . . C20 C 0.4504(3) 0.32431(13) 1.0645(3) 0.0317(8) Uani 1 1 d . . . H20A H 0.4506 0.3483 1.1349 0.038 Uiso 1 1 calc R . . C21 C 0.3651(3) 0.34261(13) 0.9429(3) 0.0325(8) Uani 1 1 d . . . H21A H 0.3092 0.3791 0.9322 0.039 Uiso 1 1 calc R . . C22 C 0.3595(3) 0.30895(12) 0.8368(3) 0.0280(7) Uani 1 1 d . . . H22A H 0.2983 0.3208 0.7544 0.034 Uiso 1 1 calc R . . C23 C 0.4463(3) 0.25739(12) 0.8554(3) 0.0265(7) Uani 1 1 d . . . C24 C 0.4648(3) 0.21213(12) 0.7673(3) 0.0259(7) Uani 1 1 d . . . C25 C 0.8455(3) 0.16961(13) 0.8326(3) 0.0289(7) Uani 1 1 d . . . C26 C 0.8588(3) 0.23307(13) 0.8073(3) 0.0284(7) Uani 1 1 d . . . H26A H 0.7890 0.2535 0.7386 0.034 Uiso 1 1 calc R . . C27 C 0.9724(3) 0.26641(13) 0.8814(3) 0.0299(7) Uani 1 1 d . . . C28 C 1.0735(3) 0.23809(15) 0.9852(3) 0.0390(8) Uani 1 1 d . . . H28A H 1.1524 0.2612 1.0363 0.047 Uiso 1 1 calc R . . C29 C 1.0563(3) 0.17542(15) 1.0121(3) 0.0424(9) Uani 1 1 d . . . H29A H 1.1225 0.1560 1.0847 0.051 Uiso 1 1 calc R . . C30 C 0.9450(3) 0.14068(14) 0.9359(3) 0.0342(8) Uani 1 1 d . . . H30A H 0.9365 0.0972 0.9539 0.041 Uiso 1 1 calc R . . B1 B 0.6224(4) 0.12059(15) 0.7846(3) 0.0286(8) 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 Cl1 0.0423(5) 0.0337(4) 0.0424(5) -0.0029(3) 0.0153(4) -0.0081(4) O1 0.0294(13) 0.0327(11) 0.0322(13) -0.0050(9) 0.0143(10) -0.0064(9) N1 0.0295(15) 0.0239(13) 0.0239(14) -0.0003(10) 0.0118(12) 0.0000(11) N2 0.0293(15) 0.0251(13) 0.0309(16) 0.0003(11) 0.0129(13) 0.0009(11) N3 0.0308(15) 0.0241(13) 0.0265(15) -0.0022(10) 0.0114(12) -0.0015(11) N4 0.0298(15) 0.0273(13) 0.0270(15) 0.0001(11) 0.0090(12) 0.0007(11) N5 0.0293(15) 0.0238(12) 0.0252(15) -0.0013(10) 0.0087(12) -0.0018(11) N6 0.0342(16) 0.0235(13) 0.0264(15) -0.0017(10) 0.0117(13) -0.0026(11) C1 0.0323(19) 0.0248(15) 0.0239(17) 0.0011(13) 0.0106(15) -0.0013(13) C2 0.0310(19) 0.0297(16) 0.0237(17) -0.0036(13) 0.0125(15) -0.0029(13) C3 0.034(2) 0.0299(16) 0.0292(18) -0.0031(14) 0.0119(16) 0.0017(14) C4 0.028(2) 0.0384(18) 0.037(2) -0.0053(15) 0.0076(16) 0.0005(15) C5 0.0331(19) 0.0371(18) 0.0319(19) -0.0096(14) 0.0110(16) -0.0079(15) C6 0.0318(19) 0.0261(15) 0.0308(18) -0.0027(13) 0.0148(16) -0.0025(13) C7 0.0288(18) 0.0268(15) 0.0247(17) -0.0011(12) 0.0141(15) -0.0013(13) C8 0.0305(19) 0.0222(15) 0.0275(18) -0.0036(12) 0.0136(15) -0.0039(13) C9 0.0290(18) 0.0251(16) 0.0291(18) -0.0057(13) 0.0123(15) -0.0024(13) C10 0.0262(18) 0.0276(16) 0.0332(18) 0.0032(13) 0.0137(15) 0.0023(13) C11 0.0298(19) 0.0236(16) 0.039(2) -0.0007(13) 0.0128(16) -0.0020(13) C12 0.036(2) 0.0302(17) 0.040(2) 0.0067(15) 0.0149(17) -0.0014(14) C13 0.0303(19) 0.0393(18) 0.0321(19) 0.0089(15) 0.0123(16) 0.0040(14) C14 0.0296(19) 0.0315(17) 0.0330(19) -0.0001(14) 0.0112(15) -0.0003(14) C15 0.0232(17) 0.0249(15) 0.0315(19) 0.0024(13) 0.0116(14) 0.0004(12) C16 0.0238(18) 0.0294(16) 0.0241(18) -0.0028(13) 0.0064(14) -0.0017(13) C17 0.0268(18) 0.0266(15) 0.0237(18) -0.0031(12) 0.0089(14) -0.0038(13) C18 0.0282(18) 0.0235(15) 0.0271(17) -0.0022(12) 0.0101(14) -0.0044(13) C19 0.0321(19) 0.0293(16) 0.0283(18) 0.0000(13) 0.0111(15) -0.0013(14) C20 0.037(2) 0.0291(16) 0.0315(19) -0.0034(13) 0.0164(16) -0.0014(14) C21 0.034(2) 0.0295(16) 0.036(2) 0.0001(14) 0.0156(16) 0.0025(14) C22 0.0285(18) 0.0253(15) 0.0281(18) 0.0004(13) 0.0085(15) -0.0037(13) C23 0.0261(18) 0.0227(15) 0.0294(18) -0.0034(12) 0.0094(15) -0.0033(13) C24 0.0290(18) 0.0238(15) 0.0255(18) 0.0004(13) 0.0111(15) -0.0038(13) C25 0.0242(18) 0.0366(18) 0.0284(18) -0.0033(14) 0.0130(15) -0.0019(14) C26 0.0290(19) 0.0289(16) 0.0253(18) -0.0016(12) 0.0084(15) 0.0007(13) C27 0.036(2) 0.0283(16) 0.0283(18) -0.0038(13) 0.0159(16) -0.0033(14) C28 0.028(2) 0.050(2) 0.034(2) 0.0007(16) 0.0064(17) -0.0071(15) C29 0.031(2) 0.052(2) 0.038(2) 0.0107(16) 0.0062(17) 0.0043(16) C30 0.032(2) 0.0332(17) 0.038(2) 0.0042(14) 0.0137(17) 0.0015(14) B1 0.033(2) 0.0265(18) 0.022(2) -0.0018(14) 0.0065(17) -0.0021(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C27 1.731(3) . ? O1 C25 1.384(3) . ? O1 B1 1.442(4) . ? N1 C8 1.370(3) . ? N1 C1 1.371(3) . ? N1 B1 1.488(4) . ? N2 C8 1.349(3) . ? N2 C9 1.350(3) . ? N3 C9 1.367(3) . ? N3 C16 1.368(3) . ? N3 B1 1.497(4) . ? N4 C16 1.344(3) . ? N4 C17 1.348(3) . ? N5 C17 1.365(3) . ? N5 C24 1.368(4) . ? N5 B1 1.490(4) . ? N6 C1 1.352(3) . ? N6 C24 1.356(3) . ? C1 C2 1.464(4) . ? C2 C3 1.385(4) . ? C2 C7 1.419(4) . ? C3 C4 1.386(4) . ? C3 H3A 0.9500 . ? C4 C5 1.403(4) . ? C4 H4A 0.9500 . ? C5 C6 1.379(4) . ? C5 H5A 0.9500 . ? C6 C7 1.393(4) . ? C6 H6A 0.9500 . ? C7 C8 1.455(4) . ? C9 C10 1.457(4) . ? C10 C11 1.393(4) . ? C10 C15 1.420(4) . ? C11 C12 1.379(4) . ? C11 H11A 0.9500 . ? C12 C13 1.399(4) . ? C12 H12A 0.9500 . ? C13 C14 1.385(4) . ? C13 H13A 0.9500 . ? C14 C15 1.398(4) . ? C14 H14A 0.9500 . ? C15 C16 1.450(4) . ? C17 C18 1.454(4) . ? C18 C19 1.393(4) . ? C18 C23 1.427(4) . ? C19 C20 1.385(4) . ? C19 H19A 0.9500 . ? C20 C21 1.391(4) . ? C20 H20A 0.9500 . ? C21 C22 1.388(4) . ? C21 H21A 0.9500 . ? C22 C23 1.386(4) . ? C22 H22A 0.9500 . ? C23 C24 1.455(4) . ? C25 C26 1.386(4) . ? C25 C30 1.386(4) . ? C26 C27 1.370(4) . ? C26 H26A 0.9500 . ? C27 C28 1.391(4) . ? C28 C29 1.383(4) . ? C28 H28A 0.9500 . ? C29 C30 1.377(4) . ? C29 H29A 0.9500 . ? C30 H30A 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 C25 O1 B1 119.6(2) . . ? C8 N1 C1 112.9(2) . . ? C8 N1 B1 123.7(2) . . ? C1 N1 B1 122.3(2) . . ? C8 N2 C9 117.3(2) . . ? C9 N3 C16 112.7(2) . . ? C9 N3 B1 123.4(2) . . ? C16 N3 B1 123.1(2) . . ? C16 N4 C17 117.0(2) . . ? C17 N5 C24 113.3(2) . . ? C17 N5 B1 123.1(2) . . ? C24 N5 B1 122.7(2) . . ? C1 N6 C24 116.6(2) . . ? N6 C1 N1 122.9(3) . . ? N6 C1 C2 130.1(3) . . ? N1 C1 C2 105.4(2) . . ? C3 C2 C7 120.6(3) . . ? C3 C2 C1 132.2(3) . . ? C7 C2 C1 107.1(3) . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5A 119.2 . . ? C4 C5 H5A 119.2 . . ? C5 C6 C7 118.3(3) . . ? C5 C6 H6A 120.8 . . ? C7 C6 H6A 120.8 . . ? C6 C7 C2 120.2(3) . . ? C6 C7 C8 132.3(3) . . ? C2 C7 C8 107.4(2) . . ? N2 C8 N1 122.0(3) . . ? N2 C8 C7 130.9(2) . . ? N1 C8 C7 105.6(2) . . ? N2 C9 N3 122.0(2) . . ? N2 C9 C10 131.2(3) . . ? N3 C9 C10 105.5(2) . . ? C11 C10 C15 120.2(3) . . ? C11 C10 C9 132.4(3) . . ? C15 C10 C9 107.3(2) . . ? C12 C11 C10 117.9(3) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C13 122.1(3) . . ? C11 C12 H12A 118.9 . . ? C13 C12 H12A 118.9 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 117.8(3) . . ? C13 C14 H14A 121.1 . . ? C15 C14 H14A 121.1 . . ? C14 C15 C10 121.0(2) . . ? C14 C15 C16 132.0(3) . . ? C10 C15 C16 107.0(2) . . ? N4 C16 N3 122.1(2) . . ? N4 C16 C15 130.8(3) . . ? N3 C16 C15 105.9(2) . . ? N4 C17 N5 122.5(2) . . ? N4 C17 C18 130.2(3) . . ? N5 C17 C18 105.9(2) . . ? C19 C18 C23 120.5(3) . . ? C19 C18 C17 132.6(3) . . ? C23 C18 C17 106.8(2) . . ? C20 C19 C18 117.9(3) . . ? C20 C19 H19A 121.0 . . ? C18 C19 H19A 121.0 . . ? C19 C20 C21 121.3(3) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.8(3) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C23 C22 C21 117.7(3) . . ? C23 C22 H22A 121.2 . . ? C21 C22 H22A 121.2 . . ? C22 C23 C18 120.8(3) . . ? C22 C23 C24 131.8(3) . . ? C18 C23 C24 107.4(2) . . ? N6 C24 N5 122.4(2) . . ? N6 C24 C23 130.4(3) . . ? N5 C24 C23 105.4(2) . . ? O1 C25 C26 118.0(3) . . ? O1 C25 C30 122.1(3) . . ? C26 C25 C30 119.8(3) . . ? C27 C26 C25 120.1(3) . . ? C27 C26 H26A 120.0 . . ? C25 C26 H26A 120.0 . . ? C26 C27 C28 120.9(3) . . ? C26 C27 Cl1 119.7(2) . . ? C28 C27 Cl1 119.3(2) . . ? C29 C28 C27 118.3(3) . . ? C29 C28 H28A 120.8 . . ? C27 C28 H28A 120.8 . . ? C30 C29 C28 121.3(3) . . ? C30 C29 H29A 119.3 . . ? C28 C29 H29A 119.3 . . ? C29 C30 C25 119.5(3) . . ? C29 C30 H30A 120.3 . . ? C25 C30 H30A 120.3 . . ? O1 B1 N1 111.1(2) . . ? O1 B1 N5 115.3(2) . . ? N1 B1 N5 104.9(3) . . ? O1 B1 N3 116.9(3) . . ? N1 B1 N3 103.7(2) . . ? N5 B1 N3 103.6(2) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.321 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.070 data_k10270 _database_code_depnum_ccdc_archive 'CCDC 906275' #TrackingRef '2c m-BrPhO-BsubPc k10270.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-Bromophenolato)(subphthalocyaninato)boron ; _chemical_name_common ; m-BrPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B Br N6 O' _chemical_formula_sum 'C30 H16 B Br N6 O' _chemical_formula_weight 567.21 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' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.6874(3) _cell_length_b 21.2084(5) _cell_length_c 11.4373(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.0790(13) _cell_angle_gamma 90.00 _cell_volume 2384.93(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 21186 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 1.763 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.714 _exptl_absorpt_correction_T_max 0.786 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 21186 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5429 _reflns_number_gt 3465 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0471P)^2^+0.8070P] 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 5429 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Br1 Br 0.50582(3) 0.346185(15) 0.65689(3) 0.03093(13) Uani 1 1 d . . . O1 O 0.7632(2) 0.13249(9) 0.74753(19) 0.0244(5) Uani 1 1 d . . . N1 N 0.9966(2) 0.09717(11) 0.8240(2) 0.0196(6) Uani 1 1 d . . . N2 N 0.9699(2) -0.01194(11) 0.7697(2) 0.0218(6) Uani 1 1 d . . . N3 N 0.8540(2) 0.06631(11) 0.6170(2) 0.0197(6) Uani 1 1 d . . . N4 N 0.8268(2) 0.13464(11) 0.4446(2) 0.0215(6) Uani 1 1 d . . . N5 N 0.9253(2) 0.17177(11) 0.6572(2) 0.0196(6) Uani 1 1 d . . . N6 N 1.1129(2) 0.19514(11) 0.8507(2) 0.0211(6) Uani 1 1 d . . . C1 C 1.0999(3) 0.13719(13) 0.8924(3) 0.0206(7) Uani 1 1 d . . . C2 C 1.1970(3) 0.09907(13) 0.9931(3) 0.0204(7) Uani 1 1 d . . . C3 C 1.3166(3) 0.11422(15) 1.0949(3) 0.0251(7) Uani 1 1 d . . . H3A H 1.3478 0.1566 1.1101 0.030 Uiso 1 1 calc R . . C4 C 1.3889(3) 0.06596(15) 1.1734(3) 0.0285(8) Uani 1 1 d . . . H4A H 1.4700 0.0756 1.2445 0.034 Uiso 1 1 calc R . . C5 C 1.3455(3) 0.00320(15) 1.1506(3) 0.0293(8) Uani 1 1 d . . . H5A H 1.3979 -0.0289 1.2062 0.035 Uiso 1 1 calc R . . C6 C 1.2277(3) -0.01287(14) 1.0485(3) 0.0247(7) Uani 1 1 d . . . H6A H 1.1989 -0.0555 1.0330 0.030 Uiso 1 1 calc R . . C7 C 1.1524(3) 0.03513(13) 0.9689(3) 0.0199(7) Uani 1 1 d . . . C8 C 1.0296(3) 0.03516(13) 0.8528(3) 0.0208(7) Uani 1 1 d . . . C9 C 0.8884(3) 0.00499(13) 0.6506(3) 0.0207(7) Uani 1 1 d . . . C10 C 0.8427(3) -0.02976(13) 0.5304(3) 0.0211(7) Uani 1 1 d . . . C11 C 0.8411(3) -0.09356(14) 0.5021(3) 0.0279(8) Uani 1 1 d . . . H11A H 0.8769 -0.1241 0.5676 0.033 Uiso 1 1 calc R . . C12 C 0.7860(3) -0.11110(16) 0.3758(3) 0.0305(8) Uani 1 1 d . . . H12A H 0.7802 -0.1546 0.3548 0.037 Uiso 1 1 calc R . . C13 C 0.7386(3) -0.06677(15) 0.2777(3) 0.0291(8) Uani 1 1 d . . . H13A H 0.7005 -0.0807 0.1920 0.035 Uiso 1 1 calc R . . C14 C 0.7463(3) -0.00306(15) 0.3037(3) 0.0254(7) Uani 1 1 d . . . H14A H 0.7179 0.0271 0.2370 0.030 Uiso 1 1 calc R . . C15 C 0.7970(3) 0.01576(13) 0.4307(3) 0.0222(7) Uani 1 1 d . . . C16 C 0.8162(3) 0.07751(13) 0.4901(3) 0.0218(7) Uani 1 1 d . . . C17 C 0.8891(3) 0.18019(13) 0.5301(3) 0.0205(7) Uani 1 1 d . . . C18 C 0.9590(3) 0.23669(13) 0.5178(3) 0.0206(7) Uani 1 1 d . . . C19 C 0.9572(3) 0.26974(14) 0.4114(3) 0.0242(7) Uani 1 1 d . . . H19A H 0.9008 0.2567 0.3278 0.029 Uiso 1 1 calc R . . C20 C 1.0406(3) 0.32226(15) 0.4318(3) 0.0281(8) Uani 1 1 d . . . H20A H 1.0397 0.3459 0.3610 0.034 Uiso 1 1 calc R . . C21 C 1.1258(3) 0.34108(14) 0.5546(3) 0.0259(7) Uani 1 1 d . . . H21A H 1.1808 0.3776 0.5655 0.031 Uiso 1 1 calc R . . C22 C 1.1316(3) 0.30764(13) 0.6601(3) 0.0241(7) Uani 1 1 d . . . H22A H 1.1922 0.3198 0.7430 0.029 Uiso 1 1 calc R . . C23 C 1.0468(3) 0.25594(13) 0.6421(3) 0.0208(7) Uani 1 1 d . . . C24 C 1.0295(3) 0.20998(13) 0.7301(3) 0.0198(7) Uani 1 1 d . . . C25 C 0.6525(3) 0.16512(14) 0.6642(3) 0.0225(7) Uani 1 1 d . . . C26 C 0.6396(3) 0.22828(14) 0.6896(3) 0.0222(7) Uani 1 1 d . . . H26A H 0.7100 0.2489 0.7575 0.027 Uiso 1 1 calc R . . C27 C 0.5241(3) 0.26086(14) 0.6159(3) 0.0239(7) Uani 1 1 d . . . C28 C 0.4223(3) 0.23230(16) 0.5140(3) 0.0332(8) Uani 1 1 d . . . H28A H 0.3429 0.2551 0.4637 0.040 Uiso 1 1 calc R . . C29 C 0.4380(3) 0.17047(17) 0.4869(3) 0.0360(9) Uani 1 1 d . . . H29A H 0.3699 0.1509 0.4156 0.043 Uiso 1 1 calc R . . C30 C 0.5522(3) 0.13586(15) 0.5621(3) 0.0298(8) Uani 1 1 d . . . H30A H 0.5610 0.0928 0.5436 0.036 Uiso 1 1 calc R . . B1 B 0.8756(4) 0.11830(16) 0.7120(3) 0.0207(8) 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 Br1 0.0355(2) 0.02570(19) 0.0327(2) 0.00402(14) 0.01455(16) 0.00767(15) O1 0.0255(12) 0.0254(11) 0.0225(12) 0.0052(9) 0.0097(10) 0.0056(9) N1 0.0237(14) 0.0178(13) 0.0184(14) -0.0002(10) 0.0095(12) 0.0012(11) N2 0.0231(14) 0.0205(13) 0.0219(15) 0.0006(11) 0.0089(12) -0.0012(11) N3 0.0210(14) 0.0158(13) 0.0210(15) 0.0010(10) 0.0069(12) 0.0017(10) N4 0.0243(14) 0.0210(13) 0.0177(14) 0.0011(11) 0.0068(12) 0.0003(11) N5 0.0256(14) 0.0157(12) 0.0160(14) -0.0007(10) 0.0065(12) 0.0001(11) N6 0.0270(14) 0.0148(12) 0.0200(14) -0.0008(10) 0.0074(12) 0.0008(11) C1 0.0257(17) 0.0193(15) 0.0166(16) -0.0013(12) 0.0079(14) 0.0012(13) C2 0.0257(17) 0.0191(15) 0.0180(16) 0.0010(13) 0.0104(14) -0.0010(13) C3 0.0301(18) 0.0246(17) 0.0197(17) 0.0001(13) 0.0089(15) -0.0035(14) C4 0.0269(18) 0.0306(18) 0.0234(18) 0.0038(14) 0.0049(15) 0.0004(15) C5 0.0322(19) 0.0302(18) 0.0241(19) 0.0093(15) 0.0097(16) 0.0083(15) C6 0.0307(18) 0.0216(16) 0.0259(19) 0.0023(14) 0.0153(16) 0.0025(14) C7 0.0230(16) 0.0194(15) 0.0197(17) 0.0024(13) 0.0110(14) 0.0023(13) C8 0.0261(17) 0.0192(16) 0.0200(17) 0.0013(13) 0.0122(15) 0.0006(13) C9 0.0205(16) 0.0188(15) 0.0251(18) 0.0005(13) 0.0113(14) -0.0006(13) C10 0.0216(16) 0.0189(15) 0.0224(17) -0.0018(13) 0.0083(14) -0.0019(13) C11 0.0253(18) 0.0255(17) 0.032(2) -0.0007(15) 0.0109(16) 0.0012(14) C12 0.0285(18) 0.0261(17) 0.037(2) -0.0094(15) 0.0130(17) -0.0021(15) C13 0.0307(19) 0.0319(19) 0.0262(19) -0.0106(15) 0.0127(16) -0.0056(15) C14 0.0240(17) 0.0303(18) 0.0202(18) 0.0003(14) 0.0068(14) -0.0014(14) C15 0.0214(16) 0.0217(16) 0.0235(18) -0.0022(13) 0.0089(14) -0.0023(13) C16 0.0206(16) 0.0216(16) 0.0218(18) -0.0002(13) 0.0068(14) 0.0001(13) C17 0.0202(16) 0.0192(15) 0.0197(17) 0.0023(13) 0.0051(14) 0.0051(13) C18 0.0212(17) 0.0171(15) 0.0221(17) 0.0018(13) 0.0070(14) 0.0039(12) C19 0.0280(18) 0.0223(16) 0.0234(18) 0.0012(13) 0.0112(15) 0.0037(14) C20 0.0324(19) 0.0267(17) 0.028(2) 0.0059(14) 0.0154(16) 0.0029(15) C21 0.0268(18) 0.0199(16) 0.034(2) 0.0025(14) 0.0149(16) 0.0006(14) C22 0.0271(18) 0.0185(16) 0.0248(18) -0.0006(13) 0.0084(15) 0.0032(14) C23 0.0244(17) 0.0156(15) 0.0229(17) 0.0028(13) 0.0098(14) 0.0055(13) C24 0.0227(16) 0.0155(15) 0.0194(17) -0.0017(13) 0.0063(14) 0.0030(13) C25 0.0237(17) 0.0278(18) 0.0196(17) 0.0039(13) 0.0125(15) 0.0005(14) C26 0.0211(17) 0.0251(17) 0.0182(17) 0.0006(13) 0.0053(14) 0.0006(14) C27 0.0263(18) 0.0259(17) 0.0202(17) 0.0033(14) 0.0098(15) 0.0029(14) C28 0.0235(18) 0.044(2) 0.028(2) -0.0003(16) 0.0047(16) 0.0062(16) C29 0.0256(19) 0.046(2) 0.029(2) -0.0094(16) 0.0025(17) -0.0029(16) C30 0.0283(19) 0.0279(17) 0.034(2) -0.0088(15) 0.0125(17) -0.0039(15) B1 0.0244(19) 0.0188(18) 0.0175(19) 0.0005(14) 0.0066(16) -0.0015(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C27 1.898(3) . ? O1 C25 1.380(4) . ? O1 B1 1.443(4) . ? N1 C8 1.368(4) . ? N1 C1 1.369(4) . ? N1 B1 1.488(4) . ? N2 C9 1.347(4) . ? N2 C8 1.354(4) . ? N3 C9 1.365(4) . ? N3 C16 1.367(4) . ? N3 B1 1.501(4) . ? N4 C16 1.341(4) . ? N4 C17 1.350(4) . ? N5 C17 1.363(4) . ? N5 C24 1.366(4) . ? N5 B1 1.490(4) . ? N6 C1 1.345(4) . ? N6 C24 1.353(4) . ? C1 C2 1.456(4) . ? C2 C3 1.388(4) . ? C2 C7 1.428(4) . ? C3 C4 1.381(4) . ? C3 H3A 0.9500 . ? C4 C5 1.400(4) . ? C4 H4A 0.9500 . ? C5 C6 1.383(4) . ? C5 H5A 0.9500 . ? C6 C7 1.392(4) . ? C6 H6A 0.9500 . ? C7 C8 1.456(4) . ? C9 C10 1.464(4) . ? C10 C11 1.390(4) . ? C10 C15 1.427(4) . ? C11 C12 1.381(4) . ? C11 H11A 0.9500 . ? C12 C13 1.397(5) . ? C12 H12A 0.9500 . ? C13 C14 1.379(4) . ? C13 H13A 0.9500 . ? C14 C15 1.394(4) . ? C14 H14A 0.9500 . ? C15 C16 1.453(4) . ? C17 C18 1.447(4) . ? C18 C19 1.398(4) . ? C18 C23 1.422(4) . ? C19 C20 1.388(4) . ? C19 H19A 0.9500 . ? C20 C21 1.399(4) . ? C20 H20A 0.9500 . ? C21 C22 1.380(4) . ? C21 H21A 0.9500 . ? C22 C23 1.385(4) . ? C22 H22A 0.9500 . ? C23 C24 1.465(4) . ? C25 C30 1.384(4) . ? C25 C26 1.389(4) . ? C26 C27 1.377(4) . ? C26 H26A 0.9500 . ? C27 C28 1.383(4) . ? C28 C29 1.373(5) . ? C28 H28A 0.9500 . ? C29 C30 1.395(5) . ? C29 H29A 0.9500 . ? C30 H30A 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 C25 O1 B1 119.6(2) . . ? C8 N1 C1 112.6(2) . . ? C8 N1 B1 123.5(2) . . ? C1 N1 B1 122.6(2) . . ? C9 N2 C8 117.0(2) . . ? C9 N3 C16 113.5(2) . . ? C9 N3 B1 123.3(2) . . ? C16 N3 B1 122.6(2) . . ? C16 N4 C17 117.3(3) . . ? C17 N5 C24 113.3(2) . . ? C17 N5 B1 123.3(2) . . ? C24 N5 B1 122.3(2) . . ? C1 N6 C24 117.1(2) . . ? N6 C1 N1 122.4(3) . . ? N6 C1 C2 130.3(3) . . ? N1 C1 C2 105.8(2) . . ? C3 C2 C7 120.6(3) . . ? C3 C2 C1 132.2(3) . . ? C7 C2 C1 107.1(3) . . ? C4 C3 C2 118.1(3) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 121.6(3) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C7 118.2(3) . . ? C5 C6 H6A 120.9 . . ? C7 C6 H6A 120.9 . . ? C6 C7 C2 120.3(3) . . ? C6 C7 C8 132.8(3) . . ? C2 C7 C8 106.8(2) . . ? N2 C8 N1 122.3(3) . . ? N2 C8 C7 130.4(3) . . ? N1 C8 C7 106.0(2) . . ? N2 C9 N3 122.3(3) . . ? N2 C9 C10 131.4(3) . . ? N3 C9 C10 105.2(2) . . ? C11 C10 C15 120.2(3) . . ? C11 C10 C9 132.7(3) . . ? C15 C10 C9 107.1(2) . . ? C12 C11 C10 117.9(3) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C13 122.0(3) . . ? C11 C12 H12A 119.0 . . ? C13 C12 H12A 119.0 . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C15 118.1(3) . . ? C13 C14 H14A 121.0 . . ? C15 C14 H14A 121.0 . . ? C14 C15 C10 120.7(3) . . ? C14 C15 C16 132.2(3) . . ? C10 C15 C16 107.1(3) . . ? N4 C16 N3 122.3(3) . . ? N4 C16 C15 130.6(3) . . ? N3 C16 C15 105.6(2) . . ? N4 C17 N5 122.2(3) . . ? N4 C17 C18 130.5(3) . . ? N5 C17 C18 105.7(2) . . ? C19 C18 C23 120.3(3) . . ? C19 C18 C17 131.9(3) . . ? C23 C18 C17 107.7(3) . . ? C20 C19 C18 117.9(3) . . ? C20 C19 H19A 121.1 . . ? C18 C19 H19A 121.1 . . ? C19 C20 C21 121.4(3) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.3(3) . . ? C22 C21 H21A 119.4 . . ? C20 C21 H21A 119.4 . . ? C21 C22 C23 118.3(3) . . ? C21 C22 H22A 120.9 . . ? C23 C22 H22A 120.9 . . ? C22 C23 C18 120.9(3) . . ? C22 C23 C24 132.5(3) . . ? C18 C23 C24 106.5(2) . . ? N6 C24 N5 122.5(3) . . ? N6 C24 C23 130.2(3) . . ? N5 C24 C23 105.5(2) . . ? O1 C25 C30 121.9(3) . . ? O1 C25 C26 117.9(3) . . ? C30 C25 C26 120.1(3) . . ? C27 C26 C25 119.6(3) . . ? C27 C26 H26A 120.2 . . ? C25 C26 H26A 120.2 . . ? C26 C27 C28 121.1(3) . . ? C26 C27 Br1 118.8(2) . . ? C28 C27 Br1 120.2(2) . . ? C29 C28 C27 118.9(3) . . ? C29 C28 H28A 120.5 . . ? C27 C28 H28A 120.5 . . ? C28 C29 C30 121.2(3) . . ? C28 C29 H29A 119.4 . . ? C30 C29 H29A 119.4 . . ? C25 C30 C29 119.0(3) . . ? C25 C30 H30A 120.5 . . ? C29 C30 H30A 120.5 . . ? O1 B1 N1 111.0(3) . . ? O1 B1 N5 115.6(3) . . ? N1 B1 N5 105.0(2) . . ? O1 B1 N3 116.6(3) . . ? N1 B1 N3 103.7(2) . . ? N5 B1 N3 103.6(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.701 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.090 data_k1153 _database_code_depnum_ccdc_archive 'CCDC 906276' #TrackingRef '2d m-IPhO-BsubPc solvate k1153.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-Iodophenolato)(subphthalocyaninato)boron ; _chemical_name_common (3-Iodophenolato)(subphthalocyaninato)boron _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B I N6 O' _chemical_formula_sum 'C30 H16 B I N6 O' _chemical_formula_weight 614.20 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' B B 0.0013 0.0007 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 20.5800(4) _cell_length_b 17.0942(4) _cell_length_c 16.7268(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.811(1) _cell_angle_gamma 90.00 _cell_volume 5536.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.00 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2432 _exptl_absorpt_coefficient_mu 1.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6890 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 23563 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.01 _reflns_number_total 6052 _reflns_number_gt 4776 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0329P)^2^] 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 6052 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.505989(8) 0.949236(10) -0.121810(10) 0.02254(6) Uani 1 1 d . . . O1 O 0.68755(8) 0.74967(10) 0.09583(10) 0.0220(4) Uani 1 1 d . . . N1 N 0.69598(10) 0.69177(11) 0.22876(12) 0.0162(4) Uani 1 1 d . . . N2 N 0.78764(10) 0.76549(12) 0.32371(13) 0.0191(5) Uani 1 1 d . . . N3 N 0.69117(9) 0.82974(11) 0.22327(12) 0.0158(4) Uani 1 1 d . . . N4 N 0.58047(10) 0.89015(11) 0.18431(12) 0.0171(4) Uani 1 1 d . . . N5 N 0.59123(10) 0.75529(11) 0.15643(12) 0.0169(4) Uani 1 1 d . . . N6 N 0.59098(10) 0.62001(11) 0.18889(13) 0.0190(4) Uani 1 1 d . . . C1 C 0.65989(12) 0.62532(13) 0.22952(15) 0.0174(5) Uani 1 1 d . . . C2 C 0.70644(13) 0.57565(14) 0.29415(15) 0.0192(5) Uani 1 1 d . . . C3 C 0.69941(13) 0.50095(15) 0.32373(16) 0.0215(6) Uani 1 1 d . . . H3A H 0.6594 0.4703 0.2973 0.026 Uiso 1 1 calc R . . C4 C 0.75279(14) 0.47319(15) 0.39283(17) 0.0260(6) Uani 1 1 d . . . H4A H 0.7492 0.4222 0.4135 0.031 Uiso 1 1 calc R . . C5 C 0.81113(14) 0.51680(16) 0.43297(16) 0.0252(6) Uani 1 1 d . . . H5A H 0.8463 0.4954 0.4807 0.030 Uiso 1 1 calc R . . C6 C 0.81944(13) 0.59086(15) 0.40517(15) 0.0221(6) Uani 1 1 d . . . H6A H 0.8596 0.6208 0.4331 0.027 Uiso 1 1 calc R . . C7 C 0.76710(12) 0.62033(14) 0.33500(15) 0.0188(5) Uani 1 1 d . . . C8 C 0.75650(12) 0.69690(15) 0.29479(15) 0.0191(5) Uani 1 1 d . . . C9 C 0.75198(12) 0.83091(14) 0.29093(15) 0.0177(5) Uani 1 1 d . . . C10 C 0.75579(12) 0.90846(14) 0.32855(16) 0.0193(5) Uani 1 1 d . . . C11 C 0.80656(13) 0.94438(15) 0.39641(16) 0.0237(6) Uani 1 1 d . . . H11A H 0.8488 0.9185 0.4258 0.028 Uiso 1 1 calc R . . C12 C 0.79341(13) 1.01854(16) 0.41930(17) 0.0262(6) Uani 1 1 d . . . H12A H 0.8277 1.0446 0.4642 0.031 Uiso 1 1 calc R . . C13 C 0.73068(14) 1.05625(15) 0.37783(17) 0.0244(6) Uani 1 1 d . . . H13A H 0.7232 1.1075 0.3950 0.029 Uiso 1 1 calc R . . C14 C 0.67930(13) 1.02031(15) 0.31220(16) 0.0213(5) Uani 1 1 d . . . H14A H 0.6363 1.0456 0.2855 0.026 Uiso 1 1 calc R . . C15 C 0.69200(12) 0.94640(14) 0.28626(15) 0.0180(5) Uani 1 1 d . . . C16 C 0.64960(12) 0.89230(14) 0.22319(15) 0.0174(5) Uani 1 1 d . . . C17 C 0.55230(12) 0.82014(14) 0.15584(15) 0.0177(5) Uani 1 1 d . . . C18 C 0.48183(12) 0.79173(14) 0.13595(14) 0.0173(5) Uani 1 1 d . . . C19 C 0.41872(12) 0.82963(15) 0.11865(15) 0.0218(6) Uani 1 1 d . . . H19A H 0.4163 0.8851 0.1208 0.026 Uiso 1 1 calc R . . C20 C 0.35981(13) 0.78461(16) 0.09828(16) 0.0260(6) Uani 1 1 d . . . H20A H 0.3161 0.8096 0.0843 0.031 Uiso 1 1 calc R . . C21 C 0.36296(13) 0.70295(16) 0.09779(16) 0.0247(6) Uani 1 1 d . . . H21A H 0.3213 0.6737 0.0822 0.030 Uiso 1 1 calc R . . C22 C 0.42516(13) 0.66399(15) 0.11941(16) 0.0241(6) Uani 1 1 d . . . H22A H 0.4270 0.6085 0.1224 0.029 Uiso 1 1 calc R . . C23 C 0.48515(12) 0.70789(15) 0.13667(15) 0.0202(5) Uani 1 1 d . . . C24 C 0.55762(12) 0.68667(14) 0.15761(15) 0.0182(5) Uani 1 1 d . . . C25 C 0.65271(11) 0.77212(13) 0.01447(14) 0.0152(5) Uani 1 1 d . . . C26 C 0.60698(11) 0.83490(13) -0.00680(15) 0.0160(5) Uani 1 1 d . . . H26A H 0.5982 0.8647 0.0364 0.019 Uiso 1 1 calc R . . C27 C 0.57434(12) 0.85348(14) -0.09161(15) 0.0176(5) Uani 1 1 d . . . C28 C 0.58701(12) 0.81227(14) -0.15579(15) 0.0205(5) Uani 1 1 d . . . H28A H 0.5643 0.8256 -0.2137 0.025 Uiso 1 1 calc R . . C29 C 0.63369(13) 0.75100(14) -0.13348(16) 0.0215(6) Uani 1 1 d . . . H29A H 0.6435 0.7225 -0.1768 0.026 Uiso 1 1 calc R . . C30 C 0.66617(12) 0.73056(14) -0.04972(16) 0.0182(5) Uani 1 1 d . . . H30A H 0.6978 0.6881 -0.0358 0.022 Uiso 1 1 calc R . . B1 B 0.66641(14) 0.75809(16) 0.16925(17) 0.0170(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02241(10) 0.02320(10) 0.01949(9) 0.00136(7) 0.00379(7) 0.00658(8) O1 0.0210(9) 0.0292(10) 0.0164(9) 0.0044(8) 0.0071(7) 0.0098(8) N1 0.0169(10) 0.0138(10) 0.0169(10) 0.0006(8) 0.0045(8) 0.0040(9) N2 0.0164(10) 0.0193(11) 0.0218(11) 0.0013(9) 0.0068(9) 0.0041(9) N3 0.0151(10) 0.0137(10) 0.0195(11) 0.0035(8) 0.0071(8) 0.0024(9) N4 0.0180(11) 0.0174(11) 0.0162(10) 0.0027(8) 0.0061(8) 0.0038(9) N5 0.0181(10) 0.0142(10) 0.0172(10) 0.0023(8) 0.0047(8) 0.0047(9) N6 0.0203(11) 0.0168(11) 0.0179(11) -0.0006(8) 0.0038(9) 0.0015(9) C1 0.0210(13) 0.0155(12) 0.0163(12) 0.0004(10) 0.0070(10) 0.0036(11) C2 0.0231(13) 0.0179(12) 0.0177(12) 0.0019(10) 0.0083(10) 0.0084(11) C3 0.0255(13) 0.0175(13) 0.0239(14) -0.0008(10) 0.0116(11) 0.0019(12) C4 0.0372(16) 0.0189(13) 0.0261(15) 0.0070(11) 0.0162(13) 0.0079(13) C5 0.0307(15) 0.0236(14) 0.0199(13) 0.0062(11) 0.0069(12) 0.0121(13) C6 0.0222(14) 0.0251(14) 0.0168(13) -0.0007(11) 0.0037(11) 0.0091(12) C7 0.0214(13) 0.0194(13) 0.0174(12) 0.0002(10) 0.0093(10) 0.0059(11) C8 0.0176(13) 0.0235(14) 0.0176(13) 0.0025(10) 0.0076(10) 0.0059(11) C9 0.0152(12) 0.0206(13) 0.0179(12) 0.0032(10) 0.0064(10) 0.0015(11) C10 0.0205(13) 0.0168(13) 0.0221(13) 0.0032(10) 0.0092(11) -0.0011(11) C11 0.0225(13) 0.0246(14) 0.0238(14) 0.0041(11) 0.0077(11) 0.0017(12) C12 0.0255(14) 0.0269(14) 0.0231(14) -0.0063(12) 0.0041(11) -0.0087(13) C13 0.0303(15) 0.0186(14) 0.0275(14) -0.0041(11) 0.0140(12) -0.0024(12) C14 0.0213(13) 0.0192(13) 0.0248(14) 0.0035(11) 0.0097(11) 0.0023(11) C15 0.0199(12) 0.0182(13) 0.0186(12) 0.0038(10) 0.0100(10) 0.0008(11) C16 0.0208(13) 0.0158(12) 0.0189(13) 0.0051(10) 0.0110(10) 0.0052(11) C17 0.0212(13) 0.0195(13) 0.0135(12) 0.0036(10) 0.0071(10) 0.0031(11) C18 0.0177(12) 0.0201(13) 0.0144(12) 0.0002(10) 0.0059(10) 0.0023(11) C19 0.0219(13) 0.0234(14) 0.0207(13) 0.0025(11) 0.0081(11) 0.0048(12) C20 0.0184(13) 0.0382(17) 0.0226(14) 0.0025(12) 0.0086(11) 0.0059(13) C21 0.0194(13) 0.0323(16) 0.0240(14) 0.0033(11) 0.0095(11) -0.0035(12) C22 0.0264(14) 0.0233(14) 0.0211(13) 0.0003(11) 0.0059(11) -0.0047(12) C23 0.0223(13) 0.0225(13) 0.0159(13) 0.0002(10) 0.0067(10) 0.0011(11) C24 0.0205(13) 0.0193(13) 0.0140(12) -0.0003(10) 0.0047(10) 0.0016(11) C25 0.0143(12) 0.0165(12) 0.0141(12) 0.0033(9) 0.0038(9) -0.0026(10) C26 0.0168(12) 0.0157(12) 0.0170(12) -0.0017(9) 0.0076(10) -0.0024(11) C27 0.0161(12) 0.0151(12) 0.0216(13) 0.0006(10) 0.0065(10) -0.0020(11) C28 0.0220(13) 0.0223(14) 0.0142(12) -0.0016(10) 0.0020(10) -0.0016(11) C29 0.0236(13) 0.0202(13) 0.0203(13) -0.0081(10) 0.0068(11) -0.0007(12) C30 0.0183(12) 0.0138(12) 0.0224(13) -0.0005(10) 0.0069(10) 0.0033(11) B1 0.0179(14) 0.0181(14) 0.0147(13) 0.0026(11) 0.0049(11) 0.0032(12) _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 I1 C27 2.105(2) . ? O1 C25 1.361(3) . ? O1 B1 1.442(3) . ? N1 C8 1.359(3) . ? N1 C1 1.360(3) . ? N1 B1 1.495(3) . ? N2 C8 1.345(3) . ? N2 C9 1.348(3) . ? N3 C16 1.369(3) . ? N3 C9 1.374(3) . ? N3 B1 1.505(3) . ? N4 C17 1.345(3) . ? N4 C16 1.349(3) . ? N5 C24 1.365(3) . ? N5 C17 1.366(3) . ? N5 B1 1.489(3) . ? N6 C24 1.342(3) . ? N6 C1 1.352(3) . ? C1 C2 1.451(3) . ? C2 C3 1.395(3) . ? C2 C7 1.425(3) . ? C3 C4 1.381(4) . ? C3 H3A 0.9500 . ? C4 C5 1.379(4) . ? C4 H4A 0.9500 . ? C5 C6 1.379(4) . ? C5 H5A 0.9500 . ? C6 C7 1.391(3) . ? C6 H6A 0.9500 . ? C7 C8 1.454(3) . ? C9 C10 1.458(3) . ? C10 C11 1.398(3) . ? C10 C15 1.419(3) . ? C11 C12 1.377(4) . ? C11 H11A 0.9500 . ? C12 C13 1.399(4) . ? C12 H12A 0.9500 . ? C13 C14 1.383(4) . ? C13 H13A 0.9500 . ? C14 C15 1.389(3) . ? C14 H14A 0.9500 . ? C15 C16 1.451(3) . ? C17 C18 1.457(3) . ? C18 C19 1.391(3) . ? C18 C23 1.435(3) . ? C19 C20 1.378(4) . ? C19 H19A 0.9500 . ? C20 C21 1.398(4) . ? C20 H20A 0.9500 . ? C21 C22 1.378(4) . ? C21 H21A 0.9500 . ? C22 C23 1.389(3) . ? C22 H22A 0.9500 . ? C23 C24 1.458(3) . ? C25 C30 1.391(3) . ? C25 C26 1.392(3) . ? C26 C27 1.385(3) . ? C26 H26A 0.9500 . ? C27 C28 1.381(3) . ? C28 C29 1.384(3) . ? C28 H28A 0.9500 . ? C29 C30 1.377(3) . ? C29 H29A 0.9500 . ? C30 H30A 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 C25 O1 B1 127.92(19) . . ? C8 N1 C1 113.5(2) . . ? C8 N1 B1 123.1(2) . . ? C1 N1 B1 122.6(2) . . ? C8 N2 C9 116.7(2) . . ? C16 N3 C9 112.6(2) . . ? C16 N3 B1 123.4(2) . . ? C9 N3 B1 122.35(19) . . ? C17 N4 C16 116.9(2) . . ? C24 N5 C17 113.50(19) . . ? C24 N5 B1 122.2(2) . . ? C17 N5 B1 123.6(2) . . ? C24 N6 C1 116.7(2) . . ? N6 C1 N1 122.3(2) . . ? N6 C1 C2 130.6(2) . . ? N1 C1 C2 105.7(2) . . ? C3 C2 C7 120.0(2) . . ? C3 C2 C1 132.7(2) . . ? C7 C2 C1 107.1(2) . . ? C4 C3 C2 117.6(2) . . ? C4 C3 H3A 121.2 . . ? C2 C3 H3A 121.2 . . ? C5 C4 C3 122.4(2) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C5 C6 C7 117.9(2) . . ? C5 C6 H6A 121.1 . . ? C7 C6 H6A 121.1 . . ? C6 C7 C2 120.8(2) . . ? C6 C7 C8 131.9(2) . . ? C2 C7 C8 106.9(2) . . ? N2 C8 N1 122.8(2) . . ? N2 C8 C7 129.8(2) . . ? N1 C8 C7 105.7(2) . . ? N2 C9 N3 122.8(2) . . ? N2 C9 C10 129.5(2) . . ? N3 C9 C10 105.6(2) . . ? C11 C10 C15 121.0(2) . . ? C11 C10 C9 131.8(2) . . ? C15 C10 C9 107.2(2) . . ? C12 C11 C10 117.8(2) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C13 121.4(2) . . ? C11 C12 H12A 119.3 . . ? C13 C12 H12A 119.3 . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C15 118.5(2) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? C14 C15 C10 120.0(2) . . ? C14 C15 C16 132.5(2) . . ? C10 C15 C16 107.3(2) . . ? N4 C16 N3 122.4(2) . . ? N4 C16 C15 130.1(2) . . ? N3 C16 C15 106.0(2) . . ? N4 C17 N5 122.6(2) . . ? N4 C17 C18 130.8(2) . . ? N5 C17 C18 105.5(2) . . ? C19 C18 C23 120.4(2) . . ? C19 C18 C17 132.8(2) . . ? C23 C18 C17 106.9(2) . . ? C20 C19 C18 118.2(2) . . ? C20 C19 H19A 120.9 . . ? C18 C19 H19A 120.9 . . ? C19 C20 C21 121.4(2) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.5(2) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C21 C22 C23 118.3(2) . . ? C21 C22 H22A 120.8 . . ? C23 C22 H22A 120.8 . . ? C22 C23 C18 120.1(2) . . ? C22 C23 C24 132.9(2) . . ? C18 C23 C24 107.0(2) . . ? N6 C24 N5 122.7(2) . . ? N6 C24 C23 130.7(2) . . ? N5 C24 C23 105.3(2) . . ? O1 C25 C30 116.9(2) . . ? O1 C25 C26 123.7(2) . . ? C30 C25 C26 119.4(2) . . ? C27 C26 C25 119.3(2) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C28 C27 C26 121.7(2) . . ? C28 C27 I1 119.81(18) . . ? C26 C27 I1 118.46(17) . . ? C27 C28 C29 118.2(2) . . ? C27 C28 H28A 120.9 . . ? C29 C28 H28A 120.9 . . ? C30 C29 C28 121.3(2) . . ? C30 C29 H29A 119.4 . . ? C28 C29 H29A 119.4 . . ? C29 C30 C25 120.0(2) . . ? C29 C30 H30A 120.0 . . ? C25 C30 H30A 120.0 . . ? O1 B1 N5 118.2(2) . . ? O1 B1 N1 108.6(2) . . ? N5 B1 N1 103.9(2) . . ? O1 B1 N3 117.0(2) . . ? N5 B1 N3 103.68(19) . . ? N1 B1 N3 103.82(19) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.437 _refine_diff_density_min -0.554 _refine_diff_density_rms 0.080 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.008 492 149 ' ' 2 0.500 0.500 0.030 492 149 ' ' _platon_squeeze_details ; ; data_k11109 _database_code_depnum_ccdc_archive 'CCDC 906277' #TrackingRef '2d m-IPhO-BsubPc k11109.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-Iodophenolato)(subphthalocyaninato)boron ; _chemical_name_common (3-Iodophenolato)(subphthalocyaninato)boron _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B I N6 O' _chemical_formula_sum 'C30 H16 B I N6 O' _chemical_formula_weight 614.20 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' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.8999(4) _cell_length_b 21.4167(6) _cell_length_c 11.4529(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.2670(15) _cell_angle_gamma 90.00 _cell_volume 2437.33(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16082 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 1.353 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans woth \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16082 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 27.39 _reflns_number_total 5505 _reflns_number_gt 3204 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^+1.4234P] 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 5505 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1769 _refine_ls_wR_factor_gt 0.1365 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 I1 I -0.00327(4) 0.160020(18) 0.15356(4) 0.03647(18) Uani 1 1 d . . . O1 O 0.2643(4) 0.37766(17) 0.2472(4) 0.0271(9) Uani 1 1 d . . . N1 N 0.4964(4) 0.4081(2) 0.3240(4) 0.0229(10) Uani 1 1 d . . . N2 N 0.6035(5) 0.3091(2) 0.3527(4) 0.0244(10) Uani 1 1 d . . . N3 N 0.4172(5) 0.33323(19) 0.1580(4) 0.0205(10) Uani 1 1 d . . . N4 N 0.3193(5) 0.3692(2) -0.0576(4) 0.0251(10) Uani 1 1 d . . . N5 N 0.3555(5) 0.43808(19) 0.1144(4) 0.0232(10) Uani 1 1 d . . . N6 N 0.4755(5) 0.5153(2) 0.2663(4) 0.0239(10) Uani 1 1 d . . . C1 C 0.5332(5) 0.4689(2) 0.3522(5) 0.0215(12) Uani 1 1 d . . . C2 C 0.6560(6) 0.4682(2) 0.4689(5) 0.0232(12) Uani 1 1 d . . . C3 C 0.7358(6) 0.5149(3) 0.5478(5) 0.0262(13) Uani 1 1 d . . . H3A H 0.7100 0.5575 0.5321 0.031 Uiso 1 1 calc R . . C4 C 0.8532(6) 0.4981(3) 0.6495(6) 0.0320(14) Uani 1 1 d . . . H4A H 0.9089 0.5295 0.7043 0.038 Uiso 1 1 calc R . . C5 C 0.8920(6) 0.4353(3) 0.6735(6) 0.0333(14) Uani 1 1 d . . . H5A H 0.9730 0.4251 0.7448 0.040 Uiso 1 1 calc R . . C6 C 0.8154(6) 0.3880(3) 0.5961(5) 0.0273(13) Uani 1 1 d . . . H6A H 0.8433 0.3457 0.6118 0.033 Uiso 1 1 calc R . . C7 C 0.6958(6) 0.4045(2) 0.4944(5) 0.0240(12) Uani 1 1 d . . . C8 C 0.5950(6) 0.3671(2) 0.3926(5) 0.0241(12) Uani 1 1 d . . . C9 C 0.5195(5) 0.2944(2) 0.2324(5) 0.0224(12) Uani 1 1 d . . . C10 C 0.5324(6) 0.2475(3) 0.1449(5) 0.0258(13) Uani 1 1 d . . . C11 C 0.6149(6) 0.1962(2) 0.1638(6) 0.0289(13) Uani 1 1 d . . . H11A H 0.6751 0.1840 0.2477 0.035 Uiso 1 1 calc R . . C12 C 0.6076(6) 0.1629(2) 0.0572(6) 0.0309(14) Uani 1 1 d . . . H12A H 0.6617 0.1267 0.0690 0.037 Uiso 1 1 calc R . . C13 C 0.5237(6) 0.1813(3) -0.0657(6) 0.0310(14) Uani 1 1 d . . . H13A H 0.5220 0.1577 -0.1366 0.037 Uiso 1 1 calc R . . C14 C 0.4415(6) 0.2337(2) -0.0871(5) 0.0274(13) Uani 1 1 d . . . H14A H 0.3849 0.2467 -0.1715 0.033 Uiso 1 1 calc R . . C15 C 0.4451(5) 0.2666(2) 0.0195(5) 0.0241(12) Uani 1 1 d . . . C16 C 0.3808(6) 0.3238(2) 0.0307(5) 0.0242(12) Uani 1 1 d . . . C17 C 0.3144(6) 0.4262(2) -0.0131(5) 0.0246(12) Uani 1 1 d . . . C18 C 0.2965(5) 0.4873(2) -0.0744(5) 0.0233(12) Uani 1 1 d . . . C19 C 0.2434(6) 0.5046(3) -0.2034(6) 0.0296(13) Uani 1 1 d . . . H19A H 0.2126 0.4741 -0.2695 0.036 Uiso 1 1 calc R . . C20 C 0.2371(6) 0.5676(3) -0.2316(6) 0.0338(14) Uani 1 1 d . . . H20A H 0.1967 0.5808 -0.3184 0.041 Uiso 1 1 calc R . . C21 C 0.2894(6) 0.6123(3) -0.1344(6) 0.0339(14) Uani 1 1 d . . . H21A H 0.2852 0.6551 -0.1571 0.041 Uiso 1 1 calc R . . C22 C 0.3475(6) 0.5958(3) -0.0052(6) 0.0315(14) Uani 1 1 d . . . H22A H 0.3857 0.6265 0.0597 0.038 Uiso 1 1 calc R . . C23 C 0.3475(6) 0.5328(2) 0.0257(5) 0.0249(12) Uani 1 1 d . . . C24 C 0.3929(6) 0.4991(2) 0.1473(5) 0.0241(12) Uani 1 1 d . . . C25 C 0.1505(6) 0.3474(3) 0.1640(6) 0.0262(13) Uani 1 1 d . . . C26 C 0.1353(6) 0.2849(3) 0.1863(5) 0.0278(13) Uani 1 1 d . . . H26A H 0.2054 0.2631 0.2528 0.033 Uiso 1 1 calc R . . C27 C 0.0176(6) 0.2545(3) 0.1113(6) 0.0314(14) Uani 1 1 d . . . C28 C -0.0844(6) 0.2844(3) 0.0111(6) 0.0381(15) Uani 1 1 d . . . H28A H -0.1654 0.2632 -0.0399 0.046 Uiso 1 1 calc R . . C29 C -0.0649(7) 0.3461(3) -0.0126(6) 0.0411(16) Uani 1 1 d . . . H29A H -0.1320 0.3671 -0.0830 0.049 Uiso 1 1 calc R . . C30 C 0.0509(6) 0.3777(3) 0.0646(6) 0.0324(14) Uani 1 1 d . . . H30A H 0.0613 0.4205 0.0487 0.039 Uiso 1 1 calc R . . B1 B 0.3747(7) 0.3885(3) 0.2114(6) 0.0239(14) 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 I1 0.0409(3) 0.0296(3) 0.0459(3) -0.00775(18) 0.0248(2) -0.00920(17) O1 0.025(2) 0.026(2) 0.032(2) -0.0023(17) 0.0135(19) -0.0013(16) N1 0.023(3) 0.019(2) 0.027(3) -0.0030(19) 0.011(2) -0.0023(18) N2 0.026(3) 0.023(2) 0.026(3) 0.000(2) 0.012(2) -0.003(2) N3 0.026(3) 0.018(2) 0.018(2) 0.0000(18) 0.009(2) -0.0015(18) N4 0.023(3) 0.025(2) 0.026(3) 0.001(2) 0.008(2) 0.000(2) N5 0.020(2) 0.019(2) 0.026(3) 0.003(2) 0.005(2) 0.0042(18) N6 0.024(3) 0.021(2) 0.025(3) 0.001(2) 0.008(2) 0.0033(19) C1 0.029(3) 0.015(3) 0.024(3) -0.002(2) 0.014(3) 0.001(2) C2 0.029(3) 0.024(3) 0.016(3) -0.001(2) 0.009(3) -0.003(2) C3 0.029(3) 0.021(3) 0.030(3) -0.002(2) 0.014(3) -0.001(2) C4 0.030(3) 0.029(3) 0.032(3) -0.010(3) 0.008(3) -0.005(3) C5 0.029(3) 0.041(4) 0.028(3) -0.003(3) 0.009(3) 0.001(3) C6 0.029(3) 0.021(3) 0.034(3) -0.001(3) 0.015(3) 0.001(2) C7 0.027(3) 0.023(3) 0.025(3) -0.001(2) 0.014(3) 0.002(2) C8 0.030(3) 0.021(3) 0.026(3) -0.001(2) 0.016(3) 0.000(2) C9 0.024(3) 0.015(2) 0.026(3) 0.000(2) 0.008(3) -0.004(2) C10 0.026(3) 0.018(3) 0.029(3) 0.000(2) 0.006(3) -0.004(2) C11 0.024(3) 0.020(3) 0.036(4) 0.003(3) 0.005(3) -0.004(2) C12 0.028(3) 0.019(3) 0.048(4) -0.001(3) 0.018(3) 0.000(2) C13 0.037(4) 0.024(3) 0.040(4) -0.007(3) 0.024(3) -0.004(3) C14 0.033(3) 0.024(3) 0.025(3) 0.003(2) 0.012(3) -0.002(2) C15 0.024(3) 0.021(3) 0.028(3) -0.002(2) 0.012(3) -0.002(2) C16 0.021(3) 0.021(3) 0.027(3) 0.000(2) 0.006(3) -0.003(2) C17 0.022(3) 0.022(3) 0.030(3) -0.001(2) 0.010(3) 0.000(2) C18 0.020(3) 0.024(3) 0.024(3) 0.001(2) 0.007(2) 0.002(2) C19 0.025(3) 0.033(3) 0.031(3) -0.001(3) 0.012(3) 0.002(2) C20 0.037(4) 0.033(3) 0.035(4) 0.014(3) 0.019(3) 0.005(3) C21 0.035(4) 0.025(3) 0.043(4) 0.006(3) 0.016(3) 0.001(3) C22 0.026(3) 0.025(3) 0.039(4) 0.004(3) 0.010(3) 0.000(2) C23 0.024(3) 0.020(3) 0.029(3) 0.004(2) 0.009(3) 0.004(2) C24 0.025(3) 0.019(3) 0.027(3) 0.002(2) 0.009(3) 0.000(2) C25 0.022(3) 0.030(3) 0.030(3) -0.004(3) 0.013(3) 0.003(2) C26 0.029(3) 0.029(3) 0.025(3) -0.005(3) 0.010(3) -0.005(2) C27 0.035(4) 0.033(3) 0.032(3) -0.003(3) 0.020(3) -0.005(3) C28 0.028(4) 0.051(4) 0.031(4) -0.002(3) 0.007(3) -0.013(3) C29 0.024(4) 0.057(4) 0.034(4) 0.008(3) 0.004(3) 0.007(3) C30 0.026(3) 0.029(3) 0.041(4) 0.007(3) 0.014(3) 0.001(3) B1 0.026(4) 0.021(3) 0.021(3) -0.002(3) 0.006(3) -0.002(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 I1 C27 2.114(6) . ? O1 C25 1.376(7) . ? O1 B1 1.441(7) . ? N1 C8 1.360(7) . ? N1 C1 1.361(7) . ? N1 B1 1.481(8) . ? N2 C8 1.340(7) . ? N2 C9 1.342(7) . ? N3 C16 1.360(7) . ? N3 C9 1.371(7) . ? N3 B1 1.491(8) . ? N4 C17 1.334(7) . ? N4 C16 1.363(7) . ? N5 C17 1.364(7) . ? N5 C24 1.375(7) . ? N5 B1 1.487(8) . ? N6 C24 1.334(7) . ? N6 C1 1.358(7) . ? C1 C2 1.452(8) . ? C2 C3 1.388(7) . ? C2 C7 1.425(7) . ? C3 C4 1.378(8) . ? C3 H3A 0.9500 . ? C4 C5 1.403(8) . ? C4 H4A 0.9500 . ? C5 C6 1.377(8) . ? C5 H5A 0.9500 . ? C6 C7 1.390(8) . ? C6 H6A 0.9500 . ? C7 C8 1.467(8) . ? C9 C10 1.465(8) . ? C10 C11 1.379(8) . ? C10 C15 1.418(8) . ? C11 C12 1.388(8) . ? C11 H11A 0.9500 . ? C12 C13 1.383(9) . ? C12 H12A 0.9500 . ? C13 C14 1.394(8) . ? C13 H13A 0.9500 . ? C14 C15 1.395(7) . ? C14 H14A 0.9500 . ? C15 C16 1.443(7) . ? C17 C18 1.460(7) . ? C18 C19 1.397(8) . ? C18 C23 1.430(7) . ? C19 C20 1.383(8) . ? C19 H19A 0.9500 . ? C20 C21 1.399(9) . ? C20 H20A 0.9500 . ? C21 C22 1.395(8) . ? C21 H21A 0.9500 . ? C22 C23 1.396(7) . ? C22 H22A 0.9500 . ? C23 C24 1.462(7) . ? C25 C30 1.371(8) . ? C25 C26 1.387(8) . ? C26 C27 1.379(8) . ? C26 H26A 0.9500 . ? C27 C28 1.384(9) . ? C28 C29 1.381(9) . ? C28 H28A 0.9500 . ? C29 C30 1.384(9) . ? C29 H29A 0.9500 . ? C30 H30A 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 C25 O1 B1 119.9(4) . . ? C8 N1 C1 113.2(4) . . ? C8 N1 B1 122.2(5) . . ? C1 N1 B1 123.3(5) . . ? C8 N2 C9 117.0(5) . . ? C16 N3 C9 112.4(4) . . ? C16 N3 B1 123.7(5) . . ? C9 N3 B1 122.5(5) . . ? C17 N4 C16 117.0(5) . . ? C17 N5 C24 113.6(4) . . ? C17 N5 B1 123.4(5) . . ? C24 N5 B1 122.6(5) . . ? C24 N6 C1 117.8(5) . . ? N6 C1 N1 121.7(5) . . ? N6 C1 C2 130.6(5) . . ? N1 C1 C2 106.2(4) . . ? C3 C2 C7 120.0(5) . . ? C3 C2 C1 133.3(5) . . ? C7 C2 C1 106.6(4) . . ? C4 C3 C2 118.6(5) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C3 C4 C5 121.1(5) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 121.6(6) . . ? C6 C5 H5A 119.2 . . ? C4 C5 H5A 119.2 . . ? C5 C6 C7 117.7(5) . . ? C5 C6 H6A 121.1 . . ? C7 C6 H6A 121.1 . . ? C6 C7 C2 121.0(5) . . ? C6 C7 C8 131.8(5) . . ? C2 C7 C8 107.1(5) . . ? N2 C8 N1 123.4(5) . . ? N2 C8 C7 129.9(5) . . ? N1 C8 C7 105.3(4) . . ? N2 C9 N3 122.2(5) . . ? N2 C9 C10 130.3(5) . . ? N3 C9 C10 105.8(5) . . ? C11 C10 C15 120.8(5) . . ? C11 C10 C9 132.6(5) . . ? C15 C10 C9 106.4(5) . . ? C10 C11 C12 118.2(6) . . ? C10 C11 H11A 120.9 . . ? C12 C11 H11A 120.9 . . ? C13 C12 C11 121.6(5) . . ? C13 C12 H12A 119.2 . . ? C11 C12 H12A 119.2 . . ? C12 C13 C14 121.1(5) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C13 C14 C15 117.9(5) . . ? C13 C14 H14A 121.1 . . ? C15 C14 H14A 121.1 . . ? C14 C15 C10 120.4(5) . . ? C14 C15 C16 131.7(5) . . ? C10 C15 C16 107.6(5) . . ? N3 C16 N4 121.8(5) . . ? N3 C16 C15 106.4(5) . . ? N4 C16 C15 130.4(5) . . ? N4 C17 N5 122.2(5) . . ? N4 C17 C18 131.0(5) . . ? N5 C17 C18 105.6(4) . . ? C19 C18 C23 121.5(5) . . ? C19 C18 C17 131.4(5) . . ? C23 C18 C17 107.1(5) . . ? C20 C19 C18 117.7(5) . . ? C20 C19 H19A 121.2 . . ? C18 C19 H19A 121.2 . . ? C19 C20 C21 121.1(6) . . ? C19 C20 H20A 119.4 . . ? C21 C20 H20A 119.4 . . ? C22 C21 C20 122.0(5) . . ? C22 C21 H21A 119.0 . . ? C20 C21 H21A 119.0 . . ? C21 C22 C23 117.8(5) . . ? C21 C22 H22A 121.1 . . ? C23 C22 H22A 121.1 . . ? C22 C23 C18 119.7(5) . . ? C22 C23 C24 133.1(5) . . ? C18 C23 C24 107.2(5) . . ? N6 C24 N5 121.8(5) . . ? N6 C24 C23 131.9(5) . . ? N5 C24 C23 105.2(5) . . ? C30 C25 O1 122.2(5) . . ? C30 C25 C26 119.8(5) . . ? O1 C25 C26 117.9(5) . . ? C27 C26 C25 119.5(6) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C26 C27 C28 121.5(6) . . ? C26 C27 I1 118.0(5) . . ? C28 C27 I1 120.5(4) . . ? C29 C28 C27 118.0(6) . . ? C29 C28 H28A 121.0 . . ? C27 C28 H28A 121.0 . . ? C28 C29 C30 121.1(6) . . ? C28 C29 H29A 119.5 . . ? C30 C29 H29A 119.5 . . ? C25 C30 C29 120.1(6) . . ? C25 C30 H30A 120.0 . . ? C29 C30 H30A 120.0 . . ? O1 B1 N1 110.6(5) . . ? O1 B1 N5 116.8(5) . . ? N1 B1 N5 104.4(4) . . ? O1 B1 N3 115.2(5) . . ? N1 B1 N3 105.3(5) . . ? N5 B1 N3 103.5(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.035 _refine_diff_density_min -1.585 _refine_diff_density_rms 0.161 data_k11169 _database_code_depnum_ccdc_archive 'CCDC 906278' #TrackingRef '4a o-FPhO-BsubPc k11169.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Fluorophenolato)(subphthalocyaninato)boron ; _chemical_name_common ; o-FPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B F N6 O' _chemical_formula_sum 'C30 H16 B F N6 O' _chemical_formula_weight 506.30 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' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1276(3) _cell_length_b 10.8350(3) _cell_length_c 11.8593(4) _cell_angle_alpha 86.4627(15) _cell_angle_beta 77.0822(13) _cell_angle_gamma 64.9040(15) _cell_volume 1147.87(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 23467 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.098 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23467 _diffrn_reflns_av_R_equivalents 0.0701 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.44 _reflns_number_total 5219 _reflns_number_gt 3567 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0837P)^2^+0.4627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5219 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 F1 F 0.55326(16) 0.83994(13) 0.31734(12) 0.0460(4) Uani 1 1 d . . . O1 O 0.59854(15) 0.58683(14) 0.39846(11) 0.0289(3) Uani 1 1 d . . . N1 N 0.85645(18) 0.41361(16) 0.36359(14) 0.0268(4) Uani 1 1 d . . . N2 N 0.82458(19) 0.20737(17) 0.37159(14) 0.0285(4) Uani 1 1 d . . . N3 N 0.69558(18) 0.38903(16) 0.25879(14) 0.0262(4) Uani 1 1 d . . . N4 N 0.66656(18) 0.50354(16) 0.08126(15) 0.0284(4) Uani 1 1 d . . . N5 N 0.78034(18) 0.56060(16) 0.21226(14) 0.0262(4) Uani 1 1 d . . . N6 N 0.98618(19) 0.54964(16) 0.28280(15) 0.0289(4) Uani 1 1 d . . . C1 C 0.9725(2) 0.4504(2) 0.35228(17) 0.0278(4) Uani 1 1 d . . . C2 C 1.0841(2) 0.3430(2) 0.40319(17) 0.0282(4) Uani 1 1 d . . . C3 C 1.2251(2) 0.3247(2) 0.41407(19) 0.0349(5) Uani 1 1 d . . . H3A H 1.2600 0.3931 0.3915 0.042 Uiso 1 1 calc R . . C4 C 1.3130(3) 0.2047(2) 0.45845(19) 0.0374(5) Uani 1 1 d . . . H4A H 1.4090 0.1910 0.4678 0.045 Uiso 1 1 calc R . . C5 C 1.2628(2) 0.1030(2) 0.48980(18) 0.0355(5) Uani 1 1 d . . . H5A H 1.3254 0.0216 0.5206 0.043 Uiso 1 1 calc R . . C6 C 1.1248(2) 0.1173(2) 0.47726(17) 0.0300(5) Uani 1 1 d . . . H6A H 1.0927 0.0467 0.4981 0.036 Uiso 1 1 calc R . . C7 C 1.0337(2) 0.2384(2) 0.43310(16) 0.0276(4) Uani 1 1 d . . . C8 C 0.8926(2) 0.28156(19) 0.39734(17) 0.0274(4) Uani 1 1 d . . . C9 C 0.7328(2) 0.2595(2) 0.29730(17) 0.0274(4) Uani 1 1 d . . . C10 C 0.6864(2) 0.1922(2) 0.22173(17) 0.0275(4) Uani 1 1 d . . . C11 C 0.6934(2) 0.0607(2) 0.21767(18) 0.0298(5) Uani 1 1 d . . . H11A H 0.7285 -0.0026 0.2750 0.036 Uiso 1 1 calc R . . C12 C 0.6476(2) 0.0255(2) 0.12772(19) 0.0342(5) Uani 1 1 d . . . H12A H 0.6484 -0.0623 0.1252 0.041 Uiso 1 1 calc R . . C13 C 0.6002(2) 0.1157(2) 0.04083(19) 0.0335(5) Uani 1 1 d . . . H13A H 0.5698 0.0881 -0.0196 0.040 Uiso 1 1 calc R . . C14 C 0.5968(2) 0.2451(2) 0.04114(18) 0.0311(5) Uani 1 1 d . . . H14A H 0.5678 0.3052 -0.0195 0.037 Uiso 1 1 calc R . . C15 C 0.6371(2) 0.2840(2) 0.13267(17) 0.0273(4) Uani 1 1 d . . . C16 C 0.6554(2) 0.4059(2) 0.15417(17) 0.0274(4) Uani 1 1 d . . . C17 C 0.7371(2) 0.57406(19) 0.10959(17) 0.0273(4) Uani 1 1 d . . . C18 C 0.8096(2) 0.65250(19) 0.03835(17) 0.0280(4) Uani 1 1 d . . . C19 C 0.8021(2) 0.7038(2) -0.07170(18) 0.0320(5) Uani 1 1 d . . . H19A H 0.7413 0.6901 -0.1156 0.038 Uiso 1 1 calc R . . C20 C 0.8867(2) 0.7755(2) -0.11493(19) 0.0346(5) Uani 1 1 d . . . H20A H 0.8802 0.8149 -0.1885 0.042 Uiso 1 1 calc R . . C21 C 0.9810(2) 0.7914(2) -0.05339(19) 0.0362(5) Uani 1 1 d . . . H21A H 1.0366 0.8421 -0.0856 0.043 Uiso 1 1 calc R . . C22 C 0.9956(2) 0.7350(2) 0.05377(18) 0.0316(5) Uani 1 1 d . . . H22A H 1.0638 0.7422 0.0937 0.038 Uiso 1 1 calc R . . C23 C 0.9070(2) 0.66747(19) 0.10073(17) 0.0278(4) Uani 1 1 d . . . C24 C 0.8935(2) 0.59839(19) 0.20960(18) 0.0280(4) Uani 1 1 d . . . C25 C 0.4734(2) 0.6647(2) 0.35725(17) 0.0282(5) Uani 1 1 d . . . C26 C 0.4503(2) 0.7932(2) 0.31499(18) 0.0317(5) Uani 1 1 d . . . C27 C 0.3272(3) 0.8730(2) 0.2725(2) 0.0422(6) Uani 1 1 d . . . H27A H 0.3146 0.9605 0.2444 0.051 Uiso 1 1 calc R . . C28 C 0.2210(3) 0.8245(3) 0.2711(2) 0.0485(6) Uani 1 1 d . . . H28A H 0.1348 0.8791 0.2420 0.058 Uiso 1 1 calc R . . C29 C 0.2401(3) 0.6972(3) 0.3118(2) 0.0447(6) Uani 1 1 d . . . H29A H 0.1677 0.6638 0.3100 0.054 Uiso 1 1 calc R . . C30 C 0.3650(2) 0.6183(2) 0.35532(19) 0.0363(5) Uani 1 1 d . . . H30A H 0.3769 0.5313 0.3843 0.044 Uiso 1 1 calc R . . B1 B 0.7237(3) 0.4936(2) 0.3138(2) 0.0273(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 F1 0.0523(9) 0.0381(7) 0.0524(8) 0.0054(6) -0.0121(7) -0.0238(6) O1 0.0288(7) 0.0312(7) 0.0266(7) 0.0007(6) -0.0054(6) -0.0128(6) N1 0.0283(9) 0.0269(9) 0.0268(8) 0.0007(7) -0.0061(7) -0.0131(7) N2 0.0313(9) 0.0307(9) 0.0257(8) 0.0034(7) -0.0071(7) -0.0152(7) N3 0.0270(9) 0.0255(8) 0.0276(9) 0.0035(7) -0.0073(7) -0.0120(7) N4 0.0272(9) 0.0259(8) 0.0308(9) 0.0030(7) -0.0070(7) -0.0098(7) N5 0.0262(9) 0.0263(8) 0.0272(9) 0.0022(7) -0.0064(7) -0.0120(7) N6 0.0303(9) 0.0260(9) 0.0316(9) 0.0009(7) -0.0084(7) -0.0121(7) C1 0.0314(11) 0.0291(10) 0.0266(10) -0.0015(8) -0.0060(8) -0.0159(9) C2 0.0317(11) 0.0288(10) 0.0248(10) -0.0015(8) -0.0083(8) -0.0120(9) C3 0.0351(12) 0.0395(12) 0.0361(12) 0.0003(9) -0.0110(10) -0.0197(10) C4 0.0335(12) 0.0417(13) 0.0374(12) -0.0002(10) -0.0139(10) -0.0128(10) C5 0.0371(12) 0.0352(12) 0.0313(11) 0.0020(9) -0.0112(9) -0.0108(10) C6 0.0346(11) 0.0311(11) 0.0237(10) 0.0016(8) -0.0076(9) -0.0128(9) C7 0.0314(11) 0.0299(10) 0.0212(9) -0.0009(8) -0.0059(8) -0.0126(9) C8 0.0322(11) 0.0251(10) 0.0234(9) 0.0016(8) -0.0038(8) -0.0119(8) C9 0.0282(10) 0.0287(10) 0.0257(10) 0.0036(8) -0.0045(8) -0.0135(8) C10 0.0261(10) 0.0295(10) 0.0278(10) -0.0004(8) -0.0035(8) -0.0135(8) C11 0.0321(11) 0.0274(10) 0.0297(10) 0.0030(8) -0.0043(9) -0.0137(9) C12 0.0358(12) 0.0322(11) 0.0358(11) -0.0010(9) -0.0061(9) -0.0162(9) C13 0.0333(11) 0.0350(11) 0.0359(11) -0.0015(9) -0.0109(9) -0.0159(9) C14 0.0312(11) 0.0324(11) 0.0326(11) 0.0041(9) -0.0119(9) -0.0141(9) C15 0.0249(10) 0.0282(10) 0.0291(10) 0.0022(8) -0.0055(8) -0.0120(8) C16 0.0258(10) 0.0286(10) 0.0268(10) 0.0011(8) -0.0073(8) -0.0097(8) C17 0.0269(10) 0.0255(10) 0.0266(10) 0.0011(8) -0.0060(8) -0.0081(8) C18 0.0279(10) 0.0220(9) 0.0305(10) -0.0005(8) -0.0029(8) -0.0085(8) C19 0.0312(11) 0.0282(10) 0.0306(11) -0.0012(8) -0.0034(9) -0.0081(9) C20 0.0365(12) 0.0286(11) 0.0304(11) 0.0044(9) -0.0011(9) -0.0094(9) C21 0.0317(11) 0.0321(11) 0.0393(12) 0.0024(9) 0.0023(10) -0.0133(9) C22 0.0275(11) 0.0284(10) 0.0360(11) 0.0008(9) -0.0025(9) -0.0111(9) C23 0.0251(10) 0.0230(10) 0.0300(10) 0.0011(8) -0.0029(8) -0.0066(8) C24 0.0258(10) 0.0246(10) 0.0324(11) -0.0003(8) -0.0036(8) -0.0109(8) C25 0.0245(10) 0.0315(11) 0.0231(10) -0.0024(8) -0.0020(8) -0.0078(8) C26 0.0323(11) 0.0328(11) 0.0290(10) -0.0024(9) -0.0037(9) -0.0137(9) C27 0.0480(14) 0.0361(12) 0.0318(12) -0.0003(10) -0.0120(11) -0.0057(11) C28 0.0342(13) 0.0604(16) 0.0385(13) -0.0110(12) -0.0130(11) -0.0040(12) C29 0.0305(12) 0.0606(16) 0.0394(13) -0.0108(11) -0.0033(10) -0.0163(11) C30 0.0289(11) 0.0465(13) 0.0339(11) -0.0053(10) -0.0028(9) -0.0173(10) B1 0.0295(12) 0.0286(11) 0.0260(11) 0.0027(9) -0.0065(9) -0.0143(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 F1 C26 1.345(2) . ? O1 C25 1.370(2) . ? O1 B1 1.451(3) . ? N1 C1 1.370(3) . ? N1 C8 1.375(2) . ? N1 B1 1.487(3) . ? N2 C8 1.345(3) . ? N2 C9 1.348(3) . ? N3 C9 1.368(2) . ? N3 C16 1.369(3) . ? N3 B1 1.496(3) . ? N4 C17 1.345(3) . ? N4 C16 1.351(3) . ? N5 C17 1.363(3) . ? N5 C24 1.365(3) . ? N5 B1 1.498(3) . ? N6 C24 1.342(3) . ? N6 C1 1.350(3) . ? C1 C2 1.449(3) . ? C2 C3 1.391(3) . ? C2 C7 1.425(3) . ? C3 C4 1.380(3) . ? C3 H3A 0.9500 . ? C4 C5 1.397(3) . ? C4 H4A 0.9500 . ? C5 C6 1.380(3) . ? C5 H5A 0.9500 . ? C6 C7 1.397(3) . ? C6 H6A 0.9500 . ? C7 C8 1.456(3) . ? C9 C10 1.454(3) . ? C10 C11 1.399(3) . ? C10 C15 1.428(3) . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 C13 1.395(3) . ? C12 H12A 0.9500 . ? C13 C14 1.388(3) . ? C13 H13A 0.9500 . ? C14 C15 1.387(3) . ? C14 H14A 0.9500 . ? C15 C16 1.454(3) . ? C17 C18 1.463(3) . ? C18 C19 1.392(3) . ? C18 C23 1.422(3) . ? C19 C20 1.386(3) . ? C19 H19A 0.9500 . ? C20 C21 1.394(3) . ? C20 H20A 0.9500 . ? C21 C22 1.387(3) . ? C21 H21A 0.9500 . ? C22 C23 1.391(3) . ? C22 H22A 0.9500 . ? C23 C24 1.461(3) . ? C25 C26 1.391(3) . ? C25 C30 1.392(3) . ? C26 C27 1.367(3) . ? C27 C28 1.386(4) . ? C27 H27A 0.9500 . ? C28 C29 1.381(4) . ? C28 H28A 0.9500 . ? C29 C30 1.384(3) . ? C29 H29A 0.9500 . ? C30 H30A 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 C25 O1 B1 115.22(16) . . ? C1 N1 C8 112.74(17) . . ? C1 N1 B1 122.25(16) . . ? C8 N1 B1 122.99(17) . . ? C8 N2 C9 117.58(17) . . ? C9 N3 C16 113.25(16) . . ? C9 N3 B1 123.00(17) . . ? C16 N3 B1 122.79(16) . . ? C17 N4 C16 116.39(17) . . ? C17 N5 C24 113.75(16) . . ? C17 N5 B1 123.19(17) . . ? C24 N5 B1 122.60(17) . . ? C24 N6 C1 116.85(17) . . ? N6 C1 N1 123.18(18) . . ? N6 C1 C2 129.18(19) . . ? N1 C1 C2 105.91(16) . . ? C3 C2 C7 120.87(19) . . ? C3 C2 C1 131.38(19) . . ? C7 C2 C1 107.39(17) . . ? C4 C3 C2 118.4(2) . . ? C4 C3 H3A 120.8 . . ? C2 C3 H3A 120.8 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C6 C5 C4 121.9(2) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C7 118.2(2) . . ? C5 C6 H6A 120.9 . . ? C7 C6 H6A 120.9 . . ? C6 C7 C2 119.80(19) . . ? C6 C7 C8 132.81(19) . . ? C2 C7 C8 107.08(17) . . ? N2 C8 N1 122.34(18) . . ? N2 C8 C7 130.18(18) . . ? N1 C8 C7 105.54(17) . . ? N2 C9 N3 122.06(18) . . ? N2 C9 C10 130.63(18) . . ? N3 C9 C10 105.55(16) . . ? C11 C10 C15 119.76(19) . . ? C11 C10 C9 132.78(19) . . ? C15 C10 C9 107.24(17) . . ? C12 C11 C10 118.13(19) . . ? C12 C11 H11A 120.9 . . ? C10 C11 H11A 120.9 . . ? C11 C12 C13 121.7(2) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C15 C14 C13 117.99(19) . . ? C15 C14 H14A 121.0 . . ? C13 C14 H14A 121.0 . . ? C14 C15 C10 121.21(18) . . ? C14 C15 C16 131.43(18) . . ? C10 C15 C16 107.03(17) . . ? N4 C16 N3 122.85(18) . . ? N4 C16 C15 129.95(19) . . ? N3 C16 C15 105.65(16) . . ? N4 C17 N5 122.69(17) . . ? N4 C17 C18 130.74(18) . . ? N5 C17 C18 105.40(17) . . ? C19 C18 C23 120.72(19) . . ? C19 C18 C17 132.2(2) . . ? C23 C18 C17 107.02(17) . . ? C20 C19 C18 117.5(2) . . ? C20 C19 H19A 121.2 . . ? C18 C19 H19A 121.2 . . ? C19 C20 C21 121.7(2) . . ? C19 C20 H20A 119.1 . . ? C21 C20 H20A 119.1 . . ? C22 C21 C20 121.4(2) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C21 C22 C23 117.6(2) . . ? C21 C22 H22A 121.2 . . ? C23 C22 H22A 121.2 . . ? C22 C23 C18 120.81(19) . . ? C22 C23 C24 131.9(2) . . ? C18 C23 C24 107.30(17) . . ? N6 C24 N5 122.23(17) . . ? N6 C24 C23 130.90(18) . . ? N5 C24 C23 105.27(17) . . ? O1 C25 C26 121.09(18) . . ? O1 C25 C30 121.50(19) . . ? C26 C25 C30 117.4(2) . . ? F1 C26 C27 119.3(2) . . ? F1 C26 C25 118.10(19) . . ? C27 C26 C25 122.6(2) . . ? C26 C27 C28 119.0(2) . . ? C26 C27 H27A 120.5 . . ? C28 C27 H27A 120.5 . . ? C29 C28 C27 120.2(2) . . ? C29 C28 H28A 119.9 . . ? C27 C28 H28A 119.9 . . ? C28 C29 C30 119.9(2) . . ? C28 C29 H29A 120.1 . . ? C30 C29 H29A 120.1 . . ? C29 C30 C25 120.9(2) . . ? C29 C30 H30A 119.5 . . ? C25 C30 H30A 119.5 . . ? O1 B1 N1 112.54(17) . . ? O1 B1 N3 115.72(17) . . ? N1 B1 N3 104.76(16) . . ? O1 B1 N5 114.71(17) . . ? N1 B1 N5 104.58(17) . . ? N3 B1 N5 103.31(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.585 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.058 data_k11191 _database_code_depnum_ccdc_archive 'CCDC 906279' #TrackingRef '4b o-ClPhO-BsubPc k11191.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Chlorophenolato)(subphthalocyaninato)boron ; _chemical_name_common ; o-ClPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B Cl N6 O' _chemical_formula_sum 'C30 H16 B Cl N6 O' _chemical_formula_weight 522.75 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.0880(2) _cell_length_b 42.9323(14) _cell_length_c 13.7269(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.3790(15) _cell_angle_gamma 90.00 _cell_volume 4702.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 21445 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.4 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.202 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.551 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21445 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -51 _diffrn_reflns_limit_k_max 55 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 27.42 _reflns_number_total 10246 _reflns_number_gt 6323 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0726P)^2^+3.1805P] 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 10246 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1708 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cl1A Cl 0.28879(10) 0.65639(2) 0.49727(5) 0.0420(2) Uani 1 1 d . . . O1A O 0.4993(2) 0.63290(4) 0.68161(14) 0.0289(4) Uani 1 1 d . . . N1A N 0.8860(3) 0.63460(5) 0.86923(17) 0.0296(5) Uani 1 1 d . . . N2A N 0.8006(3) 0.62508(5) 0.69741(17) 0.0282(5) Uani 1 1 d . . . N3A N 0.8457(3) 0.62762(5) 0.53083(18) 0.0320(6) Uani 1 1 d . . . N4A N 0.6857(3) 0.66674(5) 0.59632(16) 0.0279(5) Uani 1 1 d . . . N5A N 0.6579(3) 0.71629(5) 0.67125(18) 0.0306(5) Uani 1 1 d . . . N6A N 0.7073(3) 0.67035(5) 0.76909(16) 0.0269(5) Uani 1 1 d . . . C1A C 0.8926(3) 0.61789(7) 0.7877(2) 0.0288(6) Uani 1 1 d . . . C2A C 1.0154(4) 0.59476(6) 0.7674(2) 0.0315(6) Uani 1 1 d . . . C3A C 1.1336(4) 0.57723(7) 0.8299(2) 0.0378(7) Uani 1 1 d . . . H3AA H 1.1427 0.5785 0.8997 0.045 Uiso 1 1 calc R . . C4A C 1.2368(4) 0.55790(7) 0.7860(3) 0.0425(8) Uani 1 1 d . . . H4AA H 1.3146 0.5449 0.8267 0.051 Uiso 1 1 calc R . . C5A C 1.2302(4) 0.55690(7) 0.6841(3) 0.0442(8) Uani 1 1 d . . . H5AA H 1.3066 0.5440 0.6571 0.053 Uiso 1 1 calc R . . C6A C 1.1147(4) 0.57436(7) 0.6211(2) 0.0392(7) Uani 1 1 d . . . H6AA H 1.1108 0.5737 0.5516 0.047 Uiso 1 1 calc R . . C7A C 1.0041(4) 0.59300(6) 0.6635(2) 0.0311(6) Uani 1 1 d . . . C8A C 0.8740(4) 0.61447(6) 0.6206(2) 0.0295(6) Uani 1 1 d . . . C9A C 0.7606(4) 0.65492(7) 0.5223(2) 0.0301(6) Uani 1 1 d . . . C10A C 0.7705(4) 0.68006(7) 0.4533(2) 0.0325(7) Uani 1 1 d . . . C11A C 0.8406(4) 0.68131(8) 0.3678(2) 0.0381(7) Uani 1 1 d . . . H11A H 0.8815 0.6631 0.3406 0.046 Uiso 1 1 calc R . . C12A C 0.8490(4) 0.71019(8) 0.3231(2) 0.0447(8) Uani 1 1 d . . . H12A H 0.8942 0.7116 0.2636 0.054 Uiso 1 1 calc R . . C13A C 0.7925(4) 0.73711(8) 0.3638(2) 0.0436(8) Uani 1 1 d . . . H13A H 0.7997 0.7565 0.3312 0.052 Uiso 1 1 calc R . . C14A C 0.7266(4) 0.73638(7) 0.4498(2) 0.0364(7) Uani 1 1 d . . . H14A H 0.6908 0.7550 0.4776 0.044 Uiso 1 1 calc R . . C15A C 0.7134(4) 0.70741(7) 0.4956(2) 0.0319(7) Uani 1 1 d . . . C16A C 0.6711(3) 0.69864(7) 0.5908(2) 0.0308(6) Uani 1 1 d . . . C17A C 0.6856(3) 0.70195(6) 0.7600(2) 0.0287(6) Uani 1 1 d . . . C18A C 0.7434(4) 0.71471(7) 0.8578(2) 0.0296(6) Uani 1 1 d . . . C19A C 0.7469(4) 0.74504(7) 0.8950(2) 0.0358(7) Uani 1 1 d . . . H19A H 0.6965 0.7617 0.8554 0.043 Uiso 1 1 calc R . . C20A C 0.8250(4) 0.75021(8) 0.9902(3) 0.0419(8) Uani 1 1 d . . . H20A H 0.8257 0.7706 1.0171 0.050 Uiso 1 1 calc R . . C21A C 0.9036(4) 0.72591(8) 1.0481(2) 0.0422(8) Uani 1 1 d . . . H21A H 0.9591 0.7303 1.1131 0.051 Uiso 1 1 calc R . . C22A C 0.9026(4) 0.69565(7) 1.0132(2) 0.0363(7) Uani 1 1 d . . . H22A H 0.9574 0.6794 1.0531 0.044 Uiso 1 1 calc R . . C23A C 0.8186(4) 0.68968(7) 0.9177(2) 0.0305(6) Uani 1 1 d . . . C24A C 0.8012(3) 0.66183(6) 0.8569(2) 0.0278(6) Uani 1 1 d . . . C25A C 0.3661(3) 0.65159(6) 0.6958(2) 0.0269(6) Uani 1 1 d . . . C26A C 0.2617(4) 0.66519(7) 0.6166(2) 0.0316(6) Uani 1 1 d . . . C27A C 0.1333(4) 0.68511(7) 0.6331(2) 0.0359(7) Uani 1 1 d . . . H27A H 0.0648 0.6949 0.5788 0.043 Uiso 1 1 calc R . . C28A C 0.1052(4) 0.69072(7) 0.7278(2) 0.0375(7) Uani 1 1 d . . . H28A H 0.0189 0.7046 0.7391 0.045 Uiso 1 1 calc R . . C29A C 0.2039(4) 0.67596(7) 0.8068(2) 0.0379(7) Uani 1 1 d . . . H29A H 0.1822 0.6792 0.8721 0.045 Uiso 1 1 calc R . . C30A C 0.3337(4) 0.65652(7) 0.7909(2) 0.0316(6) Uani 1 1 d . . . H30A H 0.4008 0.6465 0.8452 0.038 Uiso 1 1 calc R . . B1A B 0.6608(4) 0.64801(8) 0.6856(2) 0.0277(7) Uani 1 1 d . . . Cl1B Cl 0.94410(12) 0.46886(2) 0.70662(7) 0.0566(3) Uani 1 1 d . . . O1B O 0.8510(2) 0.43626(4) 0.88456(14) 0.0324(5) Uani 1 1 d . . . N1B N 0.5453(3) 0.39008(5) 1.00145(17) 0.0322(6) Uani 1 1 d . . . N2B N 0.5608(3) 0.43721(5) 0.91168(17) 0.0294(5) Uani 1 1 d . . . N3B N 0.4390(3) 0.47521(5) 0.79521(18) 0.0326(6) Uani 1 1 d . . . N4B N 0.6061(3) 0.43385(5) 0.74711(17) 0.0294(5) Uani 1 1 d . . . N5B N 0.6412(3) 0.38387(5) 0.67833(17) 0.0312(5) Uani 1 1 d . . . N6B N 0.6602(3) 0.39037(5) 0.85229(17) 0.0289(5) Uani 1 1 d . . . C10B C 0.4548(4) 0.45936(7) 0.6184(2) 0.0313(7) Uani 1 1 d . . . C11B C 0.3486(4) 0.47844(7) 0.5544(2) 0.0366(7) Uani 1 1 d . . . H11B H 0.2996 0.4964 0.5783 0.044 Uiso 1 1 calc R . . C12B C 0.3162(4) 0.47074(7) 0.4559(2) 0.0408(8) Uani 1 1 d . . . H12B H 0.2450 0.4838 0.4113 0.049 Uiso 1 1 calc R . . C13B C 0.3860(4) 0.44407(7) 0.4197(2) 0.0404(8) Uani 1 1 d . . . H13B H 0.3641 0.4397 0.3510 0.048 Uiso 1 1 calc R . . C14B C 0.4865(4) 0.42403(7) 0.4828(2) 0.0350(7) Uani 1 1 d . . . H14B H 0.5303 0.4056 0.4583 0.042 Uiso 1 1 calc R . . C15B C 0.5216(4) 0.43146(7) 0.5822(2) 0.0315(6) Uani 1 1 d . . . C16B C 0.6052(4) 0.41466(7) 0.6674(2) 0.0292(6) Uani 1 1 d . . . C17B C 0.6568(4) 0.37212(7) 0.7700(2) 0.0305(6) Uani 1 1 d . . . C18B C 0.6289(4) 0.34047(7) 0.8019(2) 0.0311(6) Uani 1 1 d . . . C19B C 0.6155(4) 0.31218(7) 0.7510(2) 0.0361(7) Uani 1 1 d . . . H19B H 0.6362 0.3110 0.6849 0.043 Uiso 1 1 calc R . . C20B C 0.5711(4) 0.28597(7) 0.7995(2) 0.0382(7) Uani 1 1 d . . . H20B H 0.5658 0.2663 0.7671 0.046 Uiso 1 1 calc R . . C21B C 0.5338(4) 0.28789(7) 0.8953(2) 0.0359(7) Uani 1 1 d . . . H21B H 0.5002 0.2696 0.9260 0.043 Uiso 1 1 calc R . . C22B C 0.5449(4) 0.31590(7) 0.9464(2) 0.0329(7) Uani 1 1 d . . . H22B H 0.5187 0.3170 1.0113 0.039 Uiso 1 1 calc R . . C23B C 0.5953(3) 0.34232(6) 0.9006(2) 0.0287(6) Uani 1 1 d . . . C24B C 0.6072(4) 0.37505(7) 0.9291(2) 0.0302(6) Uani 1 1 d . . . C25B C 0.9772(4) 0.42234(7) 0.8433(2) 0.0316(7) Uani 1 1 d . . . C26B C 1.0276(4) 0.43424(7) 0.7587(2) 0.0368(7) Uani 1 1 d . . . C27B C 1.1487(4) 0.41886(8) 0.7150(3) 0.0445(8) Uani 1 1 d . . . H27B H 1.1798 0.4267 0.6558 0.053 Uiso 1 1 calc R . . C28B C 1.2230(4) 0.39232(8) 0.7582(3) 0.0470(9) Uani 1 1 d . . . H28B H 1.3046 0.3816 0.7282 0.056 Uiso 1 1 calc R . . C29B C 1.1795(4) 0.38122(8) 0.8444(3) 0.0463(9) Uani 1 1 d . . . H29B H 1.2338 0.3633 0.8750 0.056 Uiso 1 1 calc R . . C30B C 1.0568(4) 0.39601(7) 0.8871(2) 0.0372(7) Uani 1 1 d . . . H30B H 1.0270 0.3881 0.9465 0.045 Uiso 1 1 calc R . . C1B C 0.5146(4) 0.42071(7) 0.9884(2) 0.0292(6) Uani 1 1 d . . . C2B C 0.4004(4) 0.44082(7) 1.0307(2) 0.0314(6) Uani 1 1 d . . . C3B C 0.3286(4) 0.43852(7) 1.1151(2) 0.0338(7) Uani 1 1 d . . . H3BA H 0.3508 0.4211 1.1578 0.041 Uiso 1 1 calc R . . C4B C 0.2234(4) 0.46228(7) 1.1359(2) 0.0357(7) Uani 1 1 d . . . H4BA H 0.1752 0.4612 1.1944 0.043 Uiso 1 1 calc R . . C5B C 0.1872(4) 0.48764(7) 1.0726(2) 0.0353(7) Uani 1 1 d . . . H5BA H 0.1151 0.5036 1.0890 0.042 Uiso 1 1 calc R . . C6B C 0.2545(3) 0.49001(7) 0.9861(2) 0.0312(6) Uani 1 1 d . . . H6BA H 0.2256 0.5069 0.9418 0.037 Uiso 1 1 calc R . . C7B C 0.3654(3) 0.46701(6) 0.9658(2) 0.0292(6) Uani 1 1 d . . . C8B C 0.4599(4) 0.46262(6) 0.8855(2) 0.0288(6) Uani 1 1 d . . . C9B C 0.5037(4) 0.45922(7) 0.7248(2) 0.0315(6) Uani 1 1 d . . . B1B B 0.6816(4) 0.42507(8) 0.8502(2) 0.0300(7) 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 Cl1A 0.0436(4) 0.0513(5) 0.0306(4) -0.0013(4) 0.0048(3) 0.0015(4) O1A 0.0300(10) 0.0222(10) 0.0358(11) -0.0006(8) 0.0092(9) -0.0006(8) N1A 0.0342(13) 0.0252(12) 0.0305(13) 0.0021(10) 0.0081(10) -0.0030(10) N2A 0.0315(13) 0.0228(12) 0.0310(13) -0.0013(10) 0.0066(10) -0.0016(10) N3A 0.0371(14) 0.0270(13) 0.0324(13) -0.0033(11) 0.0076(11) -0.0028(11) N4A 0.0319(13) 0.0229(12) 0.0285(12) 0.0004(10) 0.0041(10) -0.0001(10) N5A 0.0306(13) 0.0244(12) 0.0364(13) 0.0015(11) 0.0046(10) 0.0017(10) N6A 0.0285(12) 0.0230(12) 0.0296(12) 0.0012(10) 0.0058(10) 0.0003(10) C1A 0.0300(15) 0.0267(15) 0.0304(15) 0.0039(12) 0.0065(12) 0.0005(12) C2A 0.0317(15) 0.0213(14) 0.0421(17) 0.0009(13) 0.0081(13) -0.0021(12) C3A 0.0353(17) 0.0293(16) 0.0475(19) 0.0024(14) 0.0024(14) -0.0017(13) C4A 0.0333(17) 0.0285(16) 0.064(2) 0.0074(16) 0.0021(16) 0.0036(13) C5A 0.0376(18) 0.0295(17) 0.068(2) -0.0078(17) 0.0144(17) 0.0046(14) C6A 0.0426(18) 0.0308(17) 0.0464(19) -0.0050(15) 0.0140(15) -0.0001(14) C7A 0.0304(15) 0.0224(14) 0.0423(17) -0.0029(13) 0.0113(13) -0.0027(12) C8A 0.0359(16) 0.0226(14) 0.0316(15) -0.0031(12) 0.0101(13) -0.0039(12) C9A 0.0337(16) 0.0263(15) 0.0300(15) -0.0004(12) 0.0043(12) -0.0051(12) C10A 0.0325(15) 0.0317(16) 0.0321(16) 0.0018(13) 0.0017(12) -0.0037(13) C11A 0.0429(18) 0.0390(18) 0.0325(16) 0.0000(14) 0.0065(14) -0.0052(14) C12A 0.049(2) 0.049(2) 0.0365(17) 0.0085(16) 0.0109(15) -0.0081(17) C13A 0.0472(19) 0.0392(19) 0.0442(19) 0.0134(16) 0.0066(15) -0.0057(16) C14A 0.0339(16) 0.0335(17) 0.0404(17) 0.0084(14) 0.0015(14) -0.0004(13) C15A 0.0293(15) 0.0313(16) 0.0336(16) 0.0064(13) 0.0010(12) -0.0014(12) C16A 0.0296(15) 0.0244(15) 0.0379(16) 0.0000(13) 0.0043(13) 0.0007(12) C17A 0.0292(15) 0.0217(14) 0.0368(16) 0.0020(12) 0.0100(12) 0.0016(11) C18A 0.0316(15) 0.0274(15) 0.0324(15) -0.0015(13) 0.0130(12) -0.0018(12) C19A 0.0383(17) 0.0290(16) 0.0436(18) -0.0049(14) 0.0171(14) -0.0046(13) C20A 0.050(2) 0.0299(17) 0.051(2) -0.0132(15) 0.0243(16) -0.0103(15) C21A 0.054(2) 0.0413(19) 0.0343(17) -0.0094(15) 0.0163(15) -0.0190(16) C22A 0.0440(18) 0.0353(17) 0.0316(16) -0.0021(14) 0.0121(14) -0.0071(14) C23A 0.0332(16) 0.0291(15) 0.0321(15) -0.0045(13) 0.0139(13) -0.0042(12) C24A 0.0305(15) 0.0252(15) 0.0288(14) 0.0021(12) 0.0086(12) -0.0017(12) C25A 0.0253(14) 0.0222(14) 0.0335(15) -0.0023(12) 0.0061(12) -0.0033(11) C26A 0.0305(15) 0.0278(15) 0.0368(16) -0.0012(13) 0.0064(13) -0.0047(12) C27A 0.0287(15) 0.0343(17) 0.0432(18) 0.0062(14) 0.0016(13) -0.0030(13) C28A 0.0278(15) 0.0331(17) 0.053(2) -0.0062(15) 0.0113(14) 0.0009(13) C29A 0.0370(17) 0.0421(19) 0.0371(17) -0.0070(14) 0.0141(14) -0.0052(14) C30A 0.0316(15) 0.0298(16) 0.0341(16) 0.0030(13) 0.0079(12) -0.0033(12) B1A 0.0282(17) 0.0265(17) 0.0283(17) -0.0028(13) 0.0040(13) -0.0003(13) Cl1B 0.0541(5) 0.0485(5) 0.0705(6) 0.0266(5) 0.0203(5) 0.0044(4) O1B 0.0304(11) 0.0301(11) 0.0381(11) -0.0036(9) 0.0094(9) -0.0007(9) N1B 0.0384(14) 0.0254(13) 0.0337(13) 0.0006(11) 0.0089(11) 0.0022(11) N2B 0.0333(13) 0.0252(13) 0.0299(13) 0.0002(10) 0.0057(10) 0.0008(10) N3B 0.0375(14) 0.0260(13) 0.0347(14) 0.0004(11) 0.0075(11) -0.0028(11) N4B 0.0358(13) 0.0224(12) 0.0314(13) 0.0004(10) 0.0095(11) -0.0003(10) N5B 0.0368(14) 0.0253(13) 0.0330(13) -0.0006(11) 0.0099(11) 0.0011(11) N6B 0.0320(13) 0.0250(12) 0.0300(13) -0.0002(10) 0.0065(10) 0.0021(10) C10B 0.0391(16) 0.0243(15) 0.0319(15) 0.0010(12) 0.0097(13) -0.0065(13) C11B 0.0437(18) 0.0279(16) 0.0382(17) 0.0004(14) 0.0064(14) 0.0012(14) C12B 0.0496(19) 0.0302(17) 0.0410(18) 0.0050(14) 0.0027(15) -0.0025(14) C13B 0.0507(19) 0.0350(17) 0.0349(17) 0.0010(14) 0.0053(14) -0.0091(15) C14B 0.0432(18) 0.0293(16) 0.0336(16) -0.0001(13) 0.0099(14) -0.0052(14) C15B 0.0368(16) 0.0275(15) 0.0321(15) 0.0022(13) 0.0108(13) -0.0035(13) C16B 0.0362(16) 0.0253(15) 0.0273(15) -0.0007(12) 0.0087(12) -0.0026(12) C17B 0.0326(15) 0.0273(15) 0.0325(16) -0.0035(13) 0.0082(13) 0.0030(12) C18B 0.0351(16) 0.0244(15) 0.0342(16) -0.0009(12) 0.0064(13) 0.0042(12) C19B 0.0426(18) 0.0314(16) 0.0346(16) -0.0015(14) 0.0071(14) 0.0037(14) C20B 0.0460(19) 0.0240(15) 0.0444(18) -0.0026(14) 0.0070(15) 0.0025(14) C21B 0.0392(17) 0.0227(15) 0.0463(18) 0.0037(14) 0.0078(14) 0.0005(13) C22B 0.0337(16) 0.0270(15) 0.0382(17) 0.0038(13) 0.0064(13) 0.0023(13) C23B 0.0300(15) 0.0245(14) 0.0313(15) 0.0006(12) 0.0039(12) 0.0037(12) C24B 0.0326(16) 0.0280(15) 0.0299(15) 0.0027(12) 0.0049(12) 0.0007(12) C25B 0.0315(16) 0.0270(15) 0.0365(16) -0.0059(13) 0.0068(13) -0.0024(12) C26B 0.0350(17) 0.0327(17) 0.0426(18) 0.0052(14) 0.0056(14) -0.0040(13) C27B 0.0411(19) 0.049(2) 0.047(2) -0.0034(17) 0.0176(16) -0.0092(16) C28B 0.0326(17) 0.041(2) 0.071(2) -0.0160(18) 0.0205(17) -0.0043(15) C29B 0.0302(17) 0.0300(17) 0.076(3) -0.0008(17) -0.0003(17) 0.0012(14) C30B 0.0332(16) 0.0340(17) 0.0429(18) 0.0020(14) 0.0016(14) 0.0021(14) C1B 0.0338(16) 0.0276(15) 0.0262(14) 0.0005(12) 0.0046(12) 0.0000(12) C2B 0.0310(15) 0.0257(15) 0.0379(16) -0.0051(13) 0.0065(13) -0.0005(12) C3B 0.0381(17) 0.0290(16) 0.0360(17) -0.0024(13) 0.0113(14) -0.0039(13) C4B 0.0374(17) 0.0341(17) 0.0381(17) -0.0037(14) 0.0139(14) -0.0037(13) C5B 0.0336(16) 0.0297(16) 0.0436(18) -0.0076(14) 0.0094(14) -0.0023(13) C6B 0.0326(16) 0.0247(15) 0.0363(16) -0.0037(13) 0.0057(13) -0.0016(12) C7B 0.0295(15) 0.0260(15) 0.0325(15) -0.0038(12) 0.0066(12) -0.0020(12) C8B 0.0329(15) 0.0216(14) 0.0322(15) -0.0010(12) 0.0061(12) -0.0017(12) C9B 0.0387(16) 0.0247(15) 0.0322(16) 0.0016(12) 0.0088(13) -0.0030(13) B1B 0.0370(18) 0.0250(17) 0.0292(17) -0.0006(14) 0.0086(14) 0.0009(14) _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 Cl1A C26A 1.730(3) . ? O1A C25A 1.382(3) . ? O1A B1A 1.451(4) . ? N1A C1A 1.337(4) . ? N1A C24A 1.352(4) . ? N2A C8A 1.370(3) . ? N2A C1A 1.373(4) . ? N2A B1A 1.489(4) . ? N3A C8A 1.340(4) . ? N3A C9A 1.355(4) . ? N4A C9A 1.363(4) . ? N4A C16A 1.376(3) . ? N4A B1A 1.507(4) . ? N5A C17A 1.351(3) . ? N5A C16A 1.357(4) . ? N6A C24A 1.365(3) . ? N6A C17A 1.371(3) . ? N6A B1A 1.494(4) . ? C1A C2A 1.463(4) . ? C2A C3A 1.396(4) . ? C2A C7A 1.416(4) . ? C3A C4A 1.383(4) . ? C3A H3AA 0.9500 . ? C4A C5A 1.392(5) . ? C4A H4AA 0.9500 . ? C5A C6A 1.385(5) . ? C5A H5AA 0.9500 . ? C6A C7A 1.396(4) . ? C6A H6AA 0.9500 . ? C7A C8A 1.450(4) . ? C9A C10A 1.447(4) . ? C10A C11A 1.385(4) . ? C10A C15A 1.420(4) . ? C11A C12A 1.390(4) . ? C11A H11A 0.9500 . ? C12A C13A 1.393(5) . ? C12A H12A 0.9500 . ? C13A C14A 1.372(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.405(4) . ? C14A H14A 0.9500 . ? C15A C16A 1.454(4) . ? C17A C18A 1.454(4) . ? C18A C19A 1.397(4) . ? C18A C23A 1.428(4) . ? C19A C20A 1.373(5) . ? C19A H19A 0.9500 . ? C20A C21A 1.400(5) . ? C20A H20A 0.9500 . ? C21A C22A 1.384(4) . ? C21A H21A 0.9500 . ? C22A C23A 1.399(4) . ? C22A H22A 0.9500 . ? C23A C24A 1.452(4) . ? C25A C30A 1.388(4) . ? C25A C26A 1.391(4) . ? C26A C27A 1.392(4) . ? C27A C28A 1.377(4) . ? C27A H27A 0.9500 . ? C28A C29A 1.391(4) . ? C28A H28A 0.9500 . ? C29A C30A 1.387(4) . ? C29A H29A 0.9500 . ? C30A H30A 0.9500 . ? Cl1B C26B 1.738(3) . ? O1B C25B 1.382(3) . ? O1B B1B 1.456(4) . ? N1B C1B 1.345(4) . ? N1B C24B 1.348(4) . ? N2B C1B 1.370(4) . ? N2B C8B 1.375(3) . ? N2B B1B 1.485(4) . ? N3B C8B 1.338(4) . ? N3B C9B 1.358(4) . ? N4B C16B 1.369(3) . ? N4B C9B 1.373(4) . ? N4B B1B 1.496(4) . ? N5B C17B 1.343(4) . ? N5B C16B 1.357(4) . ? N6B C24B 1.370(3) . ? N6B C17B 1.371(4) . ? N6B B1B 1.501(4) . ? C10B C11B 1.391(4) . ? C10B C15B 1.435(4) . ? C10B C9B 1.450(4) . ? C11B C12B 1.376(4) . ? C11B H11B 0.9500 . ? C12B C13B 1.402(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.386(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.386(4) . ? C14B H14B 0.9500 . ? C15B C16B 1.445(4) . ? C17B C18B 1.456(4) . ? C18B C19B 1.397(4) . ? C18B C23B 1.428(4) . ? C19B C20B 1.384(4) . ? C19B H19B 0.9500 . ? C20B C21B 1.399(4) . ? C20B H20B 0.9500 . ? C21B C22B 1.388(4) . ? C21B H21B 0.9500 . ? C22B C23B 1.390(4) . ? C22B H22B 0.9500 . ? C23B C24B 1.458(4) . ? C25B C30B 1.388(4) . ? C25B C26B 1.389(4) . ? C26B C27B 1.396(4) . ? C27B C28B 1.376(5) . ? C27B H27B 0.9500 . ? C28B C29B 1.375(5) . ? C28B H28B 0.9500 . ? C29B C30B 1.385(4) . ? C29B H29B 0.9500 . ? C30B H30B 0.9500 . ? C1B C2B 1.453(4) . ? C2B C3B 1.381(4) . ? C2B C7B 1.433(4) . ? C3B C4B 1.387(4) . ? C3B H3BA 0.9500 . ? C4B C5B 1.394(4) . ? C4B H4BA 0.9500 . ? C5B C6B 1.388(4) . ? C5B H5BA 0.9500 . ? C6B C7B 1.392(4) . ? C6B H6BA 0.9500 . ? C7B C8B 1.452(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 C25A O1A B1A 116.9(2) . . ? C1A N1A C24A 116.6(2) . . ? C8A N2A C1A 112.5(2) . . ? C8A N2A B1A 123.6(2) . . ? C1A N2A B1A 122.5(2) . . ? C8A N3A C9A 116.9(2) . . ? C9A N4A C16A 112.0(2) . . ? C9A N4A B1A 122.9(2) . . ? C16A N4A B1A 123.6(2) . . ? C17A N5A C16A 117.1(2) . . ? C24A N6A C17A 112.9(2) . . ? C24A N6A B1A 122.6(2) . . ? C17A N6A B1A 123.5(2) . . ? N1A C1A N2A 123.1(3) . . ? N1A C1A C2A 130.1(3) . . ? N2A C1A C2A 105.3(2) . . ? C3A C2A C7A 121.0(3) . . ? C3A C2A C1A 131.8(3) . . ? C7A C2A C1A 107.1(2) . . ? C4A C3A C2A 117.2(3) . . ? C4A C3A H3AA 121.4 . . ? C2A C3A H3AA 121.4 . . ? C3A C4A C5A 121.9(3) . . ? C3A C4A H4AA 119.0 . . ? C5A C4A H4AA 119.0 . . ? C6A C5A C4A 121.5(3) . . ? C6A C5A H5AA 119.3 . . ? C4A C5A H5AA 119.3 . . ? C5A C6A C7A 117.5(3) . . ? C5A C6A H6AA 121.2 . . ? C7A C6A H6AA 121.2 . . ? C6A C7A C2A 120.7(3) . . ? C6A C7A C8A 131.8(3) . . ? C2A C7A C8A 107.4(2) . . ? N3A C8A N2A 122.5(3) . . ? N3A C8A C7A 130.2(3) . . ? N2A C8A C7A 105.9(2) . . ? N3A C9A N4A 122.6(3) . . ? N3A C9A C10A 128.4(3) . . ? N4A C9A C10A 106.8(2) . . ? C11A C10A C15A 121.3(3) . . ? C11A C10A C9A 131.1(3) . . ? C15A C10A C9A 107.0(2) . . ? C10A C11A C12A 117.7(3) . . ? C10A C11A H11A 121.2 . . ? C12A C11A H11A 121.2 . . ? C11A C12A C13A 121.4(3) . . ? C11A C12A H12A 119.3 . . ? C13A C12A H12A 119.3 . . ? C14A C13A C12A 121.7(3) . . ? C14A C13A H13A 119.2 . . ? C12A C13A H13A 119.2 . . ? C13A C14A C15A 118.2(3) . . ? C13A C14A H14A 120.9 . . ? C15A C14A H14A 120.9 . . ? C14A C15A C10A 119.7(3) . . ? C14A C15A C16A 132.6(3) . . ? C10A C15A C16A 107.1(2) . . ? N5A C16A N4A 121.9(3) . . ? N5A C16A C15A 130.4(3) . . ? N4A C16A C15A 106.1(2) . . ? N5A C17A N6A 122.2(3) . . ? N5A C17A C18A 129.9(3) . . ? N6A C17A C18A 105.8(2) . . ? C19A C18A C23A 120.6(3) . . ? C19A C18A C17A 132.3(3) . . ? C23A C18A C17A 106.9(2) . . ? C20A C19A C18A 118.5(3) . . ? C20A C19A H19A 120.7 . . ? C18A C19A H19A 120.7 . . ? C19A C20A C21A 121.0(3) . . ? C19A C20A H20A 119.5 . . ? C21A C20A H20A 119.5 . . ? C22A C21A C20A 121.8(3) . . ? C22A C21A H21A 119.1 . . ? C20A C21A H21A 119.1 . . ? C21A C22A C23A 118.1(3) . . ? C21A C22A H22A 121.0 . . ? C23A C22A H22A 121.0 . . ? C22A C23A C18A 119.9(3) . . ? C22A C23A C24A 132.6(3) . . ? C18A C23A C24A 107.2(2) . . ? N1A C24A N6A 122.7(2) . . ? N1A C24A C23A 129.8(3) . . ? N6A C24A C23A 106.0(2) . . ? O1A C25A C30A 119.5(2) . . ? O1A C25A C26A 121.4(2) . . ? C30A C25A C26A 119.1(3) . . ? C27A C26A C25A 120.3(3) . . ? C27A C26A Cl1A 120.0(2) . . ? C25A C26A Cl1A 119.6(2) . . ? C28A C27A C26A 120.2(3) . . ? C28A C27A H27A 119.9 . . ? C26A C27A H27A 119.9 . . ? C27A C28A C29A 119.7(3) . . ? C27A C28A H28A 120.2 . . ? C29A C28A H28A 120.2 . . ? C30A C29A C28A 120.3(3) . . ? C30A C29A H29A 119.9 . . ? C28A C29A H29A 119.9 . . ? C29A C30A C25A 120.3(3) . . ? C29A C30A H30A 119.9 . . ? C25A C30A H30A 119.9 . . ? O1A B1A N2A 111.8(2) . . ? O1A B1A N6A 115.4(2) . . ? N2A B1A N6A 104.4(2) . . ? O1A B1A N4A 116.5(2) . . ? N2A B1A N4A 104.0(2) . . ? N6A B1A N4A 103.4(2) . . ? C25B O1B B1B 116.4(2) . . ? C1B N1B C24B 116.9(2) . . ? C1B N2B C8B 112.7(2) . . ? C1B N2B B1B 122.8(2) . . ? C8B N2B B1B 123.2(2) . . ? C8B N3B C9B 116.8(2) . . ? C16B N4B C9B 112.0(2) . . ? C16B N4B B1B 123.6(2) . . ? C9B N4B B1B 123.4(2) . . ? C17B N5B C16B 117.1(2) . . ? C24B N6B C17B 113.1(2) . . ? C24B N6B B1B 122.9(2) . . ? C17B N6B B1B 122.6(2) . . ? C11B C10B C15B 120.1(3) . . ? C11B C10B C9B 132.6(3) . . ? C15B C10B C9B 106.8(3) . . ? C12B C11B C10B 118.6(3) . . ? C12B C11B H11B 120.7 . . ? C10B C11B H11B 120.7 . . ? C11B C12B C13B 121.4(3) . . ? C11B C12B H12B 119.3 . . ? C13B C12B H12B 119.3 . . ? C14B C13B C12B 121.0(3) . . ? C14B C13B H13B 119.5 . . ? C12B C13B H13B 119.5 . . ? C15B C14B C13B 118.5(3) . . ? C15B C14B H14B 120.7 . . ? C13B C14B H14B 120.7 . . ? C14B C15B C10B 120.3(3) . . ? C14B C15B C16B 132.6(3) . . ? C10B C15B C16B 106.8(2) . . ? N5B C16B N4B 121.7(2) . . ? N5B C16B C15B 129.8(3) . . ? N4B C16B C15B 106.7(2) . . ? N5B C17B N6B 122.9(3) . . ? N5B C17B C18B 129.5(3) . . ? N6B C17B C18B 105.6(2) . . ? C19B C18B C23B 120.8(3) . . ? C19B C18B C17B 131.7(3) . . ? C23B C18B C17B 107.2(2) . . ? C20B C19B C18B 118.1(3) . . ? C20B C19B H19B 120.9 . . ? C18B C19B H19B 120.9 . . ? C19B C20B C21B 121.1(3) . . ? C19B C20B H20B 119.4 . . ? C21B C20B H20B 119.4 . . ? C22B C21B C20B 121.4(3) . . ? C22B C21B H21B 119.3 . . ? C20B C21B H21B 119.3 . . ? C21B C22B C23B 118.5(3) . . ? C21B C22B H22B 120.7 . . ? C23B C22B H22B 120.7 . . ? C22B C23B C18B 120.0(3) . . ? C22B C23B C24B 132.6(3) . . ? C18B C23B C24B 107.1(2) . . ? N1B C24B N6B 122.5(3) . . ? N1B C24B C23B 130.0(3) . . ? N6B C24B C23B 105.8(2) . . ? O1B C25B C30B 119.8(3) . . ? O1B C25B C26B 121.4(3) . . ? C30B C25B C26B 118.9(3) . . ? C25B C26B C27B 120.5(3) . . ? C25B C26B Cl1B 120.8(2) . . ? C27B C26B Cl1B 118.7(2) . . ? C28B C27B C26B 119.7(3) . . ? C28B C27B H27B 120.2 . . ? C26B C27B H27B 120.2 . . ? C29B C28B C27B 120.2(3) . . ? C29B C28B H28B 119.9 . . ? C27B C28B H28B 119.9 . . ? C28B C29B C30B 120.4(3) . . ? C28B C29B H29B 119.8 . . ? C30B C29B H29B 119.8 . . ? C29B C30B C25B 120.3(3) . . ? C29B C30B H30B 119.9 . . ? C25B C30B H30B 119.9 . . ? N1B C1B N2B 122.7(3) . . ? N1B C1B C2B 130.0(3) . . ? N2B C1B C2B 105.7(2) . . ? C3B C2B C7B 120.6(3) . . ? C3B C2B C1B 132.4(3) . . ? C7B C2B C1B 107.0(2) . . ? C2B C3B C4B 118.4(3) . . ? C2B C3B H3BA 120.8 . . ? C4B C3B H3BA 120.8 . . ? C3B C4B C5B 121.3(3) . . ? C3B C4B H4BA 119.3 . . ? C5B C4B H4BA 119.3 . . ? C6B C5B C4B 121.2(3) . . ? C6B C5B H5BA 119.4 . . ? C4B C5B H5BA 119.4 . . ? C5B C6B C7B 118.3(3) . . ? C5B C6B H6BA 120.9 . . ? C7B C6B H6BA 120.9 . . ? C6B C7B C2B 120.1(3) . . ? C6B C7B C8B 132.8(3) . . ? C2B C7B C8B 107.1(2) . . ? N3B C8B N2B 122.9(3) . . ? N3B C8B C7B 130.4(3) . . ? N2B C8B C7B 105.6(2) . . ? N3B C9B N4B 122.0(3) . . ? N3B C9B C10B 129.9(3) . . ? N4B C9B C10B 106.5(2) . . ? O1B B1B N2B 111.8(2) . . ? O1B B1B N4B 116.1(2) . . ? N2B B1B N4B 104.1(2) . . ? O1B B1B N6B 115.2(3) . . ? N2B B1B N6B 104.4(2) . . ? N4B B1B N6B 103.7(2) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.361 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.066 data_k11190 _database_code_depnum_ccdc_archive 'CCDC 906280' #TrackingRef '4c o-BrPhO-BsubPc k11190.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Bromophenolato)(subphthalocyaninato)boron ; _chemical_name_common ; o-BrPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B Br N6 O' _chemical_formula_sum 'C30 H16 B Br N6 O' _chemical_formula_weight 567.21 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.8223(5) _cell_length_b 20.6856(11) _cell_length_c 11.5946(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.325(3) _cell_angle_gamma 90.00 _cell_volume 2401.07(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16224 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 1.751 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.724 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20402 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4227 _reflns_number_gt 2612 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.1421P)^2^+8.2012P] 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 4227 _refine_ls_number_parameters 326 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1398 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2668 _refine_ls_wR_factor_gt 0.2227 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.0076(4) 0.07604(17) 0.0387(3) 0.0542(9) Uani 0.570(10) 1 d PD A 1 Br1A Br -0.0077(8) 0.0993(5) 0.0302(8) 0.141(3) Uani 0.430(10) 1 d PD A 2 O1 O 0.2570(4) 0.13271(19) 0.2441(4) 0.0304(10) Uani 1 1 d D . . N1 N 0.4892(5) 0.0967(2) 0.3217(4) 0.0248(11) Uani 1 1 d . . . N2 N 0.4640(5) -0.0149(2) 0.2675(4) 0.0267(11) Uani 1 1 d . . . N3 N 0.3520(5) 0.0663(2) 0.1185(4) 0.0266(11) Uani 1 1 d . . . N4 N 0.3274(5) 0.1365(2) -0.0498(4) 0.0260(11) Uani 1 1 d . . . N5 N 0.4218(5) 0.1738(2) 0.1600(4) 0.0234(11) Uani 1 1 d . . . N6 N 0.6035(5) 0.1970(2) 0.3490(4) 0.0250(11) Uani 1 1 d . . . C1 C 0.5899(6) 0.1375(3) 0.3899(5) 0.0258(13) Uani 1 1 d . A . C2 C 0.6841(6) 0.0979(3) 0.4867(5) 0.0265(13) Uani 1 1 d . . . C3 C 0.8026(6) 0.1133(3) 0.5854(5) 0.0303(14) Uani 1 1 d . A . H3A H 0.8329 0.1567 0.6016 0.036 Uiso 1 1 calc R . . C4 C 0.8746(6) 0.0628(3) 0.6588(6) 0.0349(15) Uani 1 1 d . . . H4A H 0.9564 0.0720 0.7260 0.042 Uiso 1 1 calc R A . C5 C 0.8303(7) -0.0011(3) 0.6371(6) 0.0334(15) Uani 1 1 d . A . H5A H 0.8805 -0.0343 0.6913 0.040 Uiso 1 1 calc R . . C6 C 0.7146(6) -0.0167(3) 0.5379(5) 0.0290(14) Uani 1 1 d . . . H6A H 0.6866 -0.0604 0.5211 0.035 Uiso 1 1 calc R A . C7 C 0.6399(6) 0.0330(3) 0.4630(5) 0.0254(13) Uani 1 1 d . A . C8 C 0.5195(6) 0.0329(3) 0.3484(5) 0.0242(13) Uani 1 1 d . A . C9 C 0.3867(6) 0.0031(3) 0.1504(5) 0.0267(13) Uani 1 1 d . A . C10 C 0.3451(6) -0.0322(3) 0.0333(6) 0.0279(14) Uani 1 1 d . . . C11 C 0.3471(6) -0.0978(3) 0.0046(6) 0.0333(15) Uani 1 1 d . A . H11A H 0.3821 -0.1292 0.0687 0.040 Uiso 1 1 calc R . . C12 C 0.2970(6) -0.1156(3) -0.1187(6) 0.0334(15) Uani 1 1 d . . . H12A H 0.2940 -0.1601 -0.1394 0.040 Uiso 1 1 calc R A . C13 C 0.2502(6) -0.0700(3) -0.2147(6) 0.0351(15) Uani 1 1 d . A . H13A H 0.2150 -0.0842 -0.2989 0.042 Uiso 1 1 calc R . . C14 C 0.2544(6) -0.0046(3) -0.1891(5) 0.0332(15) Uani 1 1 d . . . H14A H 0.2272 0.0264 -0.2545 0.040 Uiso 1 1 calc R A . C15 C 0.2997(6) 0.0147(3) -0.0644(6) 0.0299(14) Uani 1 1 d . A . C16 C 0.3174(5) 0.0778(3) -0.0056(5) 0.0242(13) Uani 1 1 d . A . C17 C 0.3873(5) 0.1827(3) 0.0340(5) 0.0250(13) Uani 1 1 d . A . C18 C 0.4576(6) 0.2407(3) 0.0231(5) 0.0261(13) Uani 1 1 d . . . C19 C 0.4598(6) 0.2742(3) -0.0803(6) 0.0314(14) Uani 1 1 d . A . H19A H 0.4055 0.2609 -0.1625 0.038 Uiso 1 1 calc R . . C20 C 0.5433(6) 0.3273(3) -0.0603(6) 0.0339(15) Uani 1 1 d . . . H20A H 0.5438 0.3520 -0.1293 0.041 Uiso 1 1 calc R A . C21 C 0.6269(6) 0.3451(3) 0.0608(6) 0.0356(15) Uani 1 1 d . A . H21A H 0.6841 0.3813 0.0716 0.043 Uiso 1 1 calc R . . C22 C 0.6294(6) 0.3119(3) 0.1652(5) 0.0271(13) Uani 1 1 d . . . H22A H 0.6880 0.3243 0.2465 0.033 Uiso 1 1 calc R A . C23 C 0.5432(6) 0.2600(3) 0.1463(5) 0.0250(13) Uani 1 1 d . A . C24 C 0.5240(6) 0.2127(3) 0.2311(5) 0.0247(13) Uani 1 1 d . A . C25 C 0.1621(9) 0.1809(3) 0.1827(11) 0.0498(12) Uani 0.570(10) 1 d PGD A 1 C26 C 0.0446(8) 0.1589(3) 0.0908(9) 0.0498(12) Uani 0.570(10) 1 d PGD A 1 C27 C -0.0592(6) 0.2018(4) 0.0320(8) 0.0498(12) Uani 0.570(10) 1 d PGD A 1 H27A H -0.1395 0.1867 -0.0309 0.060 Uiso 0.570(10) 1 calc PR A 1 C28 C -0.0455(7) 0.2667(4) 0.0652(9) 0.0498(12) Uani 0.570(10) 1 d PG A 1 H28A H -0.1164 0.2960 0.0250 0.060 Uiso 0.570(10) 1 calc PR A 1 C29 C 0.0720(10) 0.2888(3) 0.1572(9) 0.0498(12) Uani 0.570(10) 1 d PG A 1 H29A H 0.0814 0.3332 0.1799 0.060 Uiso 0.570(10) 1 calc PR A 1 C30 C 0.1758(9) 0.2459(3) 0.2159(10) 0.0498(12) Uani 0.570(10) 1 d PG A 1 H30A H 0.2561 0.2609 0.2788 0.060 Uiso 0.570(10) 1 calc PR A 1 C25A C 0.1766(10) 0.1879(3) 0.1973(15) 0.0498(12) Uani 0.430(10) 1 d PGD A 2 C26A C 0.0478(9) 0.1746(4) 0.1138(12) 0.0498(12) Uani 0.430(10) 1 d PGD A 2 C27A C -0.0469(8) 0.2237(6) 0.0756(11) 0.0498(12) Uani 0.430(10) 1 d PGD A 2 H27B H -0.1349 0.2146 0.0185 0.060 Uiso 0.430(10) 1 calc PR A 2 C28A C -0.0126(11) 0.2861(5) 0.1209(14) 0.0498(12) Uani 0.430(10) 1 d PG A 2 H28B H -0.0773 0.3196 0.0947 0.060 Uiso 0.430(10) 1 calc PR A 2 C29A C 0.1162(14) 0.2994(3) 0.2044(14) 0.0498(12) Uani 0.430(10) 1 d PG A 2 H29B H 0.1396 0.3421 0.2353 0.060 Uiso 0.430(10) 1 calc PR A 2 C30A C 0.2108(12) 0.2503(3) 0.2426(15) 0.0498(12) Uani 0.430(10) 1 d PG A 2 H30B H 0.2989 0.2594 0.2997 0.060 Uiso 0.430(10) 1 calc PR A 2 B1 B 0.3706(7) 0.1192(3) 0.2117(6) 0.0260(15) Uani 1 1 d . A . 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 0.0332(12) 0.0867(18) 0.0358(11) 0.0042(8) 0.0054(8) -0.0189(10) Br1A 0.053(2) 0.242(8) 0.120(5) -0.062(5) 0.023(3) -0.016(4) O1 0.028(2) 0.030(2) 0.034(2) 0.0074(18) 0.0119(19) 0.0020(18) N1 0.025(3) 0.024(3) 0.024(3) -0.0010(19) 0.008(2) -0.002(2) N2 0.028(3) 0.026(3) 0.027(3) 0.001(2) 0.012(2) -0.003(2) N3 0.026(3) 0.028(3) 0.021(3) -0.001(2) 0.004(2) -0.006(2) N4 0.024(3) 0.029(3) 0.021(2) 0.000(2) 0.003(2) -0.001(2) N5 0.024(3) 0.025(3) 0.019(2) -0.0001(19) 0.005(2) 0.001(2) N6 0.028(3) 0.026(3) 0.020(2) -0.002(2) 0.007(2) 0.002(2) C1 0.033(3) 0.023(3) 0.023(3) -0.002(2) 0.012(3) -0.004(3) C2 0.028(3) 0.032(3) 0.021(3) 0.002(2) 0.012(3) -0.002(3) C3 0.036(4) 0.027(3) 0.026(3) 0.000(2) 0.009(3) 0.002(3) C4 0.029(3) 0.040(4) 0.031(3) 0.006(3) 0.006(3) 0.006(3) C5 0.041(4) 0.026(4) 0.031(3) 0.004(3) 0.011(3) 0.006(3) C6 0.039(4) 0.024(3) 0.026(3) 0.000(2) 0.014(3) 0.002(3) C7 0.030(3) 0.024(3) 0.025(3) 0.002(2) 0.014(3) 0.001(3) C8 0.024(3) 0.024(3) 0.027(3) 0.001(2) 0.012(3) -0.001(2) C9 0.027(3) 0.024(3) 0.031(3) 0.001(2) 0.012(3) -0.001(3) C10 0.026(3) 0.025(3) 0.031(3) -0.003(2) 0.010(3) -0.010(3) C11 0.026(3) 0.033(4) 0.041(4) 0.001(3) 0.013(3) -0.003(3) C12 0.030(3) 0.032(4) 0.040(4) -0.012(3) 0.015(3) -0.004(3) C13 0.028(3) 0.046(4) 0.031(3) -0.012(3) 0.011(3) -0.005(3) C14 0.028(3) 0.042(4) 0.029(3) -0.003(3) 0.011(3) -0.001(3) C15 0.022(3) 0.033(4) 0.034(3) -0.003(3) 0.009(3) -0.006(3) C16 0.018(3) 0.030(3) 0.025(3) 0.000(2) 0.008(2) -0.008(2) C17 0.020(3) 0.028(3) 0.024(3) 0.002(2) 0.004(2) -0.001(2) C18 0.025(3) 0.025(3) 0.027(3) 0.001(2) 0.009(3) 0.003(2) C19 0.036(4) 0.028(3) 0.029(3) 0.001(3) 0.012(3) 0.004(3) C20 0.041(4) 0.027(4) 0.033(3) 0.004(3) 0.013(3) 0.003(3) C21 0.036(4) 0.028(3) 0.040(4) 0.003(3) 0.012(3) -0.006(3) C22 0.025(3) 0.024(3) 0.029(3) 0.001(2) 0.007(3) -0.002(3) C23 0.024(3) 0.024(3) 0.026(3) 0.001(2) 0.008(3) 0.004(2) C24 0.025(3) 0.026(3) 0.022(3) -0.001(2) 0.008(3) 0.000(2) C25 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C26 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C27 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C28 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C29 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C30 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C25A 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C26A 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C27A 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C28A 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C29A 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) C30A 0.050(3) 0.064(3) 0.043(3) 0.005(2) 0.026(2) -0.003(2) B1 0.022(3) 0.031(4) 0.022(3) 0.005(3) 0.005(3) -0.005(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 Br1 C26 1.810(5) . ? Br1A C26A 1.812(6) . ? O1 C25A 1.412(6) . ? O1 C25 1.414(6) . ? O1 B1 1.443(8) . ? N1 C8 1.367(7) . ? N1 C1 1.367(7) . ? N1 B1 1.499(8) . ? N2 C8 1.337(7) . ? N2 C9 1.349(8) . ? N3 C16 1.364(7) . ? N3 C9 1.371(7) . ? N3 B1 1.497(9) . ? N4 C16 1.337(7) . ? N4 C17 1.341(7) . ? N5 C24 1.362(7) . ? N5 C17 1.376(7) . ? N5 B1 1.482(8) . ? N6 C1 1.348(7) . ? N6 C24 1.349(7) . ? C1 C2 1.449(8) . ? C2 C3 1.393(8) . ? C2 C7 1.417(8) . ? C3 C4 1.385(9) . ? C3 H3A 0.9500 . ? C4 C5 1.397(9) . ? C4 H4A 0.9500 . ? C5 C6 1.378(9) . ? C5 H5A 0.9500 . ? C6 C7 1.389(8) . ? C6 H6A 0.9500 . ? C7 C8 1.466(8) . ? C9 C10 1.454(8) . ? C10 C11 1.400(9) . ? C10 C15 1.429(9) . ? C11 C12 1.373(9) . ? C11 H11A 0.9500 . ? C12 C13 1.399(10) . ? C12 H12A 0.9500 . ? C13 C14 1.382(9) . ? C13 H13A 0.9500 . ? C14 C15 1.396(8) . ? C14 H14A 0.9500 . ? C15 C16 1.451(8) . ? C17 C18 1.451(8) . ? C18 C19 1.393(8) . ? C18 C23 1.433(8) . ? C19 C20 1.386(9) . ? C19 H19A 0.9500 . ? C20 C21 1.399(9) . ? C20 H20A 0.9500 . ? C21 C22 1.382(9) . ? C21 H21A 0.9500 . ? C22 C23 1.384(8) . ? C22 H22A 0.9500 . ? C23 C24 1.458(8) . ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C27 H27A 0.9500 . ? C28 C29 1.3900 . ? C28 H28A 0.9500 . ? C29 C30 1.3900 . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C25A C26A 1.3900 . ? C25A C30A 1.3900 . ? C26A C27A 1.3900 . ? C27A C28A 1.3900 . ? C27A H27B 0.9500 . ? C28A C29A 1.3900 . ? C28A H28B 0.9500 . ? C29A C30A 1.3900 . ? C29A H29B 0.9500 . ? C30A H30B 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 C25A O1 C25 9.4(4) . . ? C25A O1 B1 121.2(9) . . ? C25 O1 B1 122.2(8) . . ? C8 N1 C1 113.2(5) . . ? C8 N1 B1 123.1(5) . . ? C1 N1 B1 122.5(5) . . ? C8 N2 C9 116.4(5) . . ? C16 N3 C9 112.9(5) . . ? C16 N3 B1 122.8(5) . . ? C9 N3 B1 123.7(5) . . ? C16 N4 C17 117.2(5) . . ? C24 N5 C17 113.2(5) . . ? C24 N5 B1 123.2(5) . . ? C17 N5 B1 122.6(5) . . ? C1 N6 C24 117.6(5) . . ? N6 C1 N1 122.0(5) . . ? N6 C1 C2 130.5(5) . . ? N1 C1 C2 105.8(5) . . ? C3 C2 C7 120.9(5) . . ? C3 C2 C1 131.7(6) . . ? C7 C2 C1 107.4(5) . . ? C4 C3 C2 117.4(6) . . ? C4 C3 H3A 121.3 . . ? C2 C3 H3A 121.3 . . ? C3 C4 C5 121.9(6) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 120.8(6) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C7 118.5(6) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C6 C7 C2 120.4(5) . . ? C6 C7 C8 132.2(5) . . ? C2 C7 C8 107.2(5) . . ? N2 C8 N1 123.3(5) . . ? N2 C8 C7 130.1(5) . . ? N1 C8 C7 105.0(5) . . ? N2 C9 N3 122.4(5) . . ? N2 C9 C10 131.0(5) . . ? N3 C9 C10 105.7(5) . . ? C11 C10 C15 120.1(6) . . ? C11 C10 C9 132.9(6) . . ? C15 C10 C9 106.9(5) . . ? C12 C11 C10 118.1(6) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C11 C12 C13 121.9(6) . . ? C11 C12 H12A 119.0 . . ? C13 C12 H12A 119.0 . . ? C14 C13 C12 121.1(6) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C15 118.2(6) . . ? C13 C14 H14A 120.9 . . ? C15 C14 H14A 120.9 . . ? C14 C15 C10 120.4(6) . . ? C14 C15 C16 132.5(6) . . ? C10 C15 C16 107.1(5) . . ? N4 C16 N3 122.2(5) . . ? N4 C16 C15 130.7(5) . . ? N3 C16 C15 105.8(5) . . ? N4 C17 N5 122.4(5) . . ? N4 C17 C18 130.6(5) . . ? N5 C17 C18 105.2(5) . . ? C19 C18 C23 120.2(6) . . ? C19 C18 C17 131.8(5) . . ? C23 C18 C17 107.9(5) . . ? C20 C19 C18 118.3(6) . . ? C20 C19 H19A 120.9 . . ? C18 C19 H19A 120.9 . . ? C19 C20 C21 120.5(6) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C22 C21 C20 122.6(6) . . ? C22 C21 H21A 118.7 . . ? C20 C21 H21A 118.7 . . ? C21 C22 C23 117.3(5) . . ? C21 C22 H22A 121.4 . . ? C23 C22 H22A 121.4 . . ? C22 C23 C18 121.1(5) . . ? C22 C23 C24 132.4(5) . . ? C18 C23 C24 106.3(5) . . ? N6 C24 N5 122.1(5) . . ? N6 C24 C23 130.2(5) . . ? N5 C24 C23 106.2(5) . . ? C26 C25 C30 120.0 . . ? C26 C25 O1 115.6(5) . . ? C30 C25 O1 124.2(5) . . ? C25 C26 C27 120.0 . . ? C25 C26 Br1 126.1(4) . . ? C27 C26 Br1 113.9(4) . . ? C26 C27 C28 120.0 . . ? C26 C27 H27A 120.0 . . ? C28 C27 H27A 120.0 . . ? C29 C28 C27 120.0 . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C28 C29 C30 120.0 . . ? C28 C29 H29A 120.0 . . ? C30 C29 H29A 120.0 . . ? C29 C30 C25 120.0 . . ? C29 C30 H30A 120.0 . . ? C25 C30 H30A 120.0 . . ? C26A C25A C30A 120.0 . . ? C26A C25A O1 114.6(5) . . ? C30A C25A O1 124.6(5) . . ? C25A C26A C27A 120.0 . . ? C25A C26A Br1A 125.7(4) . . ? C27A C26A Br1A 113.8(4) . . ? C26A C27A C28A 120.0 . . ? C26A C27A H27B 120.0 . . ? C28A C27A H27B 120.0 . . ? C29A C28A C27A 120.0 . . ? C29A C28A H28B 120.0 . . ? C27A C28A H28B 120.0 . . ? C30A C29A C28A 120.0 . . ? C30A C29A H29B 120.0 . . ? C28A C29A H29B 120.0 . . ? C29A C30A C25A 120.0 . . ? C29A C30A H30B 120.0 . . ? C25A C30A H30B 120.0 . . ? O1 B1 N5 116.3(5) . . ? O1 B1 N3 115.8(5) . . ? N5 B1 N3 103.6(5) . . ? O1 B1 N1 112.2(5) . . ? N5 B1 N1 104.5(5) . . ? N3 B1 N1 102.9(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.271 _refine_diff_density_min -0.914 _refine_diff_density_rms 0.116 data_k11197 _database_code_depnum_ccdc_archive 'CCDC 906281' #TrackingRef '4d o-IPhO-BsubPc solvate k11197.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Iodophenolato)(subphthalocyaninato)boron ; _chemical_name_common (2-Iodophenolato)(subphthalocyaninato)boron _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B I N6 O, 0.5(C6 H6)' _chemical_formula_sum 'C33 H19 B I N6 O' _chemical_formula_weight 653.25 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' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.1641(3) _cell_length_b 13.8900(4) _cell_length_c 19.3994(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.6040(16) _cell_angle_gamma 90.00 _cell_volume 2714.71(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18456 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 1.220 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18456 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6189 _reflns_number_gt 4276 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0537P)^2^+6.6201P] 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 6189 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 I1 I 0.46821(3) 0.12654(2) 0.089835(16) 0.03212(12) Uani 1 1 d . . . O1 O 0.7599(3) 0.0968(2) 0.17622(14) 0.0211(6) Uani 1 1 d . . . N1 N 0.6921(3) -0.1205(2) 0.06693(17) 0.0190(7) Uani 1 1 d . . . N2 N 0.8723(3) -0.0388(2) 0.13195(17) 0.0186(7) Uani 1 1 d . . . N3 N 1.0803(4) -0.0335(2) 0.20476(18) 0.0228(8) Uani 1 1 d . . . N4 N 0.8768(3) -0.0297(2) 0.25327(17) 0.0194(7) Uani 1 1 d . . . N5 N 0.7030(4) -0.1023(3) 0.30590(17) 0.0223(8) Uani 1 1 d . . . N6 N 0.6789(3) -0.0717(2) 0.18359(17) 0.0194(7) Uani 1 1 d . . . C1 C 0.8159(4) -0.0867(3) 0.0732(2) 0.0198(9) Uani 1 1 d . . . C2 C 0.9264(4) -0.1093(3) 0.0353(2) 0.0218(9) Uani 1 1 d . . . C3 C 0.9326(5) -0.1536(3) -0.0287(2) 0.0246(9) Uani 1 1 d . . . H3A H 0.8541 -0.1745 -0.0569 0.030 Uiso 1 1 calc R . . C4 C 1.0560(5) -0.1663(3) -0.0502(2) 0.0297(11) Uani 1 1 d . . . H4A H 1.0614 -0.1945 -0.0943 0.036 Uiso 1 1 calc R . . C5 C 1.1723(5) -0.1389(3) -0.0088(2) 0.0277(10) Uani 1 1 d . . . H5A H 1.2552 -0.1483 -0.0254 0.033 Uiso 1 1 calc R . . C6 C 1.1695(5) -0.0982(3) 0.0560(2) 0.0256(10) Uani 1 1 d . . . H6A H 1.2492 -0.0824 0.0851 0.031 Uiso 1 1 calc R . . C7 C 1.0449(4) -0.0811(3) 0.0775(2) 0.0224(9) Uani 1 1 d . . . C8 C 1.0074(4) -0.0428(3) 0.1417(2) 0.0207(9) Uani 1 1 d . . . C9 C 1.0129(4) -0.0330(3) 0.2597(2) 0.0216(9) Uani 1 1 d . . . C10 C 1.0567(4) -0.0571(3) 0.3325(2) 0.0220(9) Uani 1 1 d . . . C11 C 1.1821(5) -0.0678(3) 0.3693(2) 0.0297(10) Uani 1 1 d . . . H11A H 1.2595 -0.0581 0.3475 0.036 Uiso 1 1 calc R . . C12 C 1.1913(5) -0.0931(4) 0.4387(3) 0.0364(12) Uani 1 1 d . . . H12A H 1.2762 -0.0989 0.4655 0.044 Uiso 1 1 calc R . . C13 C 1.0774(5) -0.1102(4) 0.4699(2) 0.0357(12) Uani 1 1 d . . . H13A H 1.0871 -0.1268 0.5178 0.043 Uiso 1 1 calc R . . C14 C 0.9512(5) -0.1039(3) 0.4337(2) 0.0303(11) Uani 1 1 d . . . H14A H 0.8747 -0.1178 0.4552 0.036 Uiso 1 1 calc R . . C15 C 0.9410(4) -0.0764(3) 0.3639(2) 0.0229(9) Uani 1 1 d . . . C16 C 0.8265(4) -0.0667(3) 0.3099(2) 0.0228(9) Uani 1 1 d . . . C17 C 0.6348(4) -0.1102(3) 0.2418(2) 0.0200(9) Uani 1 1 d . . . C18 C 0.5281(4) -0.1756(3) 0.2159(2) 0.0214(9) Uani 1 1 d . . . C19 C 0.4484(5) -0.2363(3) 0.2497(2) 0.0291(10) Uani 1 1 d . . . H19A H 0.4500 -0.2334 0.2987 0.035 Uiso 1 1 calc R . . C20 C 0.3666(5) -0.3011(3) 0.2101(3) 0.0330(11) Uani 1 1 d . . . H20A H 0.3119 -0.3431 0.2326 0.040 Uiso 1 1 calc R . . C21 C 0.3628(4) -0.3062(3) 0.1382(3) 0.0315(11) Uani 1 1 d . . . H21A H 0.3054 -0.3512 0.1125 0.038 Uiso 1 1 calc R . . C22 C 0.4418(4) -0.2463(3) 0.1034(2) 0.0258(10) Uani 1 1 d . . . H22A H 0.4390 -0.2501 0.0544 0.031 Uiso 1 1 calc R . . C23 C 0.5249(4) -0.1807(3) 0.1420(2) 0.0212(9) Uani 1 1 d . . . C24 C 0.6289(4) -0.1190(3) 0.1239(2) 0.0188(8) Uani 1 1 d . . . C25 C 0.6780(4) 0.1380(3) 0.2179(2) 0.0196(9) Uani 1 1 d . . . C26 C 0.5462(4) 0.1606(3) 0.1920(2) 0.0241(9) Uani 1 1 d . . . C27 C 0.4643(5) 0.2057(3) 0.2345(3) 0.0305(11) Uani 1 1 d . . . H27A H 0.3756 0.2219 0.2162 0.037 Uiso 1 1 calc R . . C28 C 0.5111(5) 0.2271(3) 0.3028(3) 0.0359(12) Uani 1 1 d . . . H28A H 0.4546 0.2568 0.3318 0.043 Uiso 1 1 calc R . . C29 C 0.6400(5) 0.2051(3) 0.3285(2) 0.0330(11) Uani 1 1 d . . . H29A H 0.6722 0.2199 0.3755 0.040 Uiso 1 1 calc R . . C30 C 0.7245(5) 0.1614(3) 0.2869(2) 0.0262(10) Uani 1 1 d . . . H30A H 0.8137 0.1476 0.3054 0.031 Uiso 1 1 calc R . . B1 B 0.7935(5) -0.0035(3) 0.1865(2) 0.0192(10) Uani 1 1 d . . . C1S C 0.5576(5) -0.0693(4) 0.4626(3) 0.0329(11) Uani 1 1 d . . . H1S H 0.5984 -0.1166 0.4370 0.039 Uiso 1 1 calc R . . C2S C 0.5201(5) 0.0179(4) 0.4321(2) 0.0311(11) Uani 1 1 d . . . H2S H 0.5327 0.0298 0.3852 0.037 Uiso 1 1 calc R . . C3S C 0.4640(5) 0.0881(4) 0.4696(2) 0.0312(11) Uani 1 1 d . . . H3S H 0.4405 0.1488 0.4490 0.037 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 I1 0.02766(18) 0.0377(2) 0.03042(18) 0.00308(14) 0.00176(12) 0.00158(14) O1 0.0204(15) 0.0218(15) 0.0222(15) 0.0022(12) 0.0063(12) 0.0030(12) N1 0.0199(18) 0.0200(17) 0.0164(16) 0.0039(14) 0.0000(13) 0.0020(15) N2 0.0186(18) 0.0207(17) 0.0174(16) 0.0020(14) 0.0054(14) 0.0020(14) N3 0.0207(18) 0.0218(18) 0.0266(19) 0.0015(15) 0.0055(15) -0.0016(15) N4 0.0180(18) 0.0219(18) 0.0185(17) -0.0003(14) 0.0034(14) 0.0017(14) N5 0.0227(19) 0.0268(19) 0.0182(17) -0.0010(15) 0.0053(15) 0.0014(15) N6 0.0163(17) 0.0217(18) 0.0207(17) 0.0009(14) 0.0048(14) 0.0006(14) C1 0.026(2) 0.018(2) 0.0166(19) 0.0036(16) 0.0039(17) 0.0032(18) C2 0.025(2) 0.022(2) 0.020(2) 0.0036(17) 0.0091(17) 0.0047(18) C3 0.033(3) 0.023(2) 0.019(2) 0.0025(17) 0.0050(18) 0.0020(19) C4 0.045(3) 0.026(2) 0.022(2) 0.0051(19) 0.015(2) 0.009(2) C5 0.027(2) 0.029(2) 0.030(2) 0.0085(19) 0.0161(19) 0.010(2) C6 0.027(2) 0.022(2) 0.028(2) 0.0082(18) 0.0063(19) 0.0045(19) C7 0.025(2) 0.019(2) 0.026(2) 0.0074(18) 0.0109(18) 0.0047(18) C8 0.022(2) 0.018(2) 0.023(2) 0.0015(17) 0.0049(17) -0.0019(17) C9 0.021(2) 0.021(2) 0.023(2) -0.0019(17) 0.0000(17) -0.0001(17) C10 0.024(2) 0.019(2) 0.022(2) -0.0033(17) -0.0028(17) 0.0008(18) C11 0.029(2) 0.026(2) 0.032(2) 0.001(2) -0.002(2) -0.002(2) C12 0.035(3) 0.035(3) 0.034(3) 0.005(2) -0.015(2) -0.006(2) C13 0.043(3) 0.039(3) 0.022(2) 0.006(2) -0.006(2) -0.003(2) C14 0.038(3) 0.031(3) 0.021(2) 0.0007(19) 0.001(2) -0.005(2) C15 0.030(2) 0.018(2) 0.020(2) -0.0023(17) -0.0027(18) 0.0018(18) C16 0.028(2) 0.025(2) 0.016(2) -0.0016(17) 0.0048(17) 0.0048(19) C17 0.018(2) 0.022(2) 0.020(2) 0.0028(17) 0.0050(16) 0.0056(17) C18 0.019(2) 0.022(2) 0.024(2) 0.0024(18) 0.0048(17) 0.0032(17) C19 0.025(2) 0.033(3) 0.031(2) 0.007(2) 0.009(2) 0.005(2) C20 0.020(2) 0.029(2) 0.050(3) 0.010(2) 0.009(2) -0.002(2) C21 0.020(2) 0.023(2) 0.050(3) -0.001(2) -0.002(2) 0.0003(19) C22 0.019(2) 0.024(2) 0.034(2) -0.0009(19) -0.0001(19) 0.0037(18) C23 0.017(2) 0.023(2) 0.023(2) 0.0037(17) -0.0005(17) 0.0056(17) C24 0.020(2) 0.019(2) 0.0169(19) 0.0029(16) -0.0011(16) 0.0006(17) C25 0.022(2) 0.016(2) 0.022(2) -0.0008(16) 0.0093(17) -0.0023(17) C26 0.027(2) 0.021(2) 0.026(2) 0.0034(18) 0.0061(19) 0.0004(18) C27 0.027(2) 0.025(2) 0.042(3) 0.004(2) 0.015(2) 0.007(2) C28 0.046(3) 0.022(2) 0.045(3) -0.002(2) 0.024(2) 0.003(2) C29 0.052(3) 0.023(2) 0.027(2) -0.0058(19) 0.017(2) -0.008(2) C30 0.026(2) 0.021(2) 0.031(2) -0.0034(19) 0.0035(19) -0.0058(19) B1 0.019(2) 0.023(2) 0.016(2) -0.0014(19) 0.0039(18) 0.0008(19) C1S 0.027(3) 0.034(3) 0.039(3) -0.008(2) 0.011(2) -0.004(2) C2S 0.030(3) 0.041(3) 0.023(2) -0.002(2) 0.0049(19) -0.012(2) C3S 0.029(3) 0.032(2) 0.033(3) 0.002(2) 0.002(2) -0.004(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 I1 C26 2.090(4) . ? O1 C25 1.361(5) . ? O1 B1 1.442(6) . ? N1 C1 1.334(5) . ? N1 C24 1.351(5) . ? N2 C8 1.363(5) . ? N2 C1 1.377(5) . ? N2 B1 1.491(6) . ? N3 C9 1.340(6) . ? N3 C8 1.350(5) . ? N4 C16 1.371(5) . ? N4 C9 1.373(5) . ? N4 B1 1.496(6) . ? N5 C16 1.342(6) . ? N5 C17 1.346(5) . ? N6 C24 1.368(5) . ? N6 C17 1.376(5) . ? N6 B1 1.497(6) . ? C1 C2 1.456(6) . ? C2 C3 1.394(6) . ? C2 C7 1.419(6) . ? C3 C4 1.384(6) . ? C3 H3A 0.9500 . ? C4 C5 1.391(7) . ? C4 H4A 0.9500 . ? C5 C6 1.382(6) . ? C5 H5A 0.9500 . ? C6 C7 1.404(6) . ? C6 H6A 0.9500 . ? C7 C8 1.451(6) . ? C9 C10 1.462(6) . ? C10 C11 1.384(6) . ? C10 C15 1.420(6) . ? C11 C12 1.383(7) . ? C11 H11A 0.9500 . ? C12 C13 1.396(8) . ? C12 H12A 0.9500 . ? C13 C14 1.382(7) . ? C13 H13A 0.9500 . ? C14 C15 1.397(6) . ? C14 H14A 0.9500 . ? C15 C16 1.466(6) . ? C17 C18 1.452(6) . ? C18 C19 1.392(6) . ? C18 C23 1.432(6) . ? C19 C20 1.386(7) . ? C19 H19A 0.9500 . ? C20 C21 1.393(7) . ? C20 H20A 0.9500 . ? C21 C22 1.391(7) . ? C21 H21A 0.9500 . ? C22 C23 1.391(6) . ? C22 H22A 0.9500 . ? C23 C24 1.440(6) . ? C25 C30 1.398(6) . ? C25 C26 1.403(6) . ? C26 C27 1.395(6) . ? C27 C28 1.380(7) . ? C27 H27A 0.9500 . ? C28 C29 1.373(7) . ? C28 H28A 0.9500 . ? C29 C30 1.392(7) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C1S C2S 1.380(7) . ? C1S C3S 1.388(7) 3_656 ? C1S H1S 0.9500 . ? C2S C3S 1.384(7) . ? C2S H2S 0.9500 . ? C3S C1S 1.388(7) 3_656 ? C3S H3S 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 C25 O1 B1 118.5(3) . . ? C1 N1 C24 117.7(3) . . ? C8 N2 C1 113.3(3) . . ? C8 N2 B1 122.7(3) . . ? C1 N2 B1 122.8(4) . . ? C9 N3 C8 116.3(4) . . ? C16 N4 C9 113.1(3) . . ? C16 N4 B1 123.8(4) . . ? C9 N4 B1 122.3(3) . . ? C16 N5 C17 116.5(3) . . ? C24 N6 C17 112.5(3) . . ? C24 N6 B1 122.3(3) . . ? C17 N6 B1 123.5(3) . . ? N1 C1 N2 122.0(4) . . ? N1 C1 C2 131.2(4) . . ? N2 C1 C2 105.0(4) . . ? C3 C2 C7 120.1(4) . . ? C3 C2 C1 132.4(4) . . ? C7 C2 C1 107.5(4) . . ? C4 C3 C2 118.2(4) . . ? C4 C3 H3A 120.9 . . ? C2 C3 H3A 120.9 . . ? C3 C4 C5 121.8(4) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C7 117.9(4) . . ? C5 C6 H6A 121.1 . . ? C7 C6 H6A 121.1 . . ? C6 C7 C2 120.8(4) . . ? C6 C7 C8 131.8(4) . . ? C2 C7 C8 107.3(4) . . ? N3 C8 N2 122.9(4) . . ? N3 C8 C7 129.6(4) . . ? N2 C8 C7 105.7(4) . . ? N3 C9 N4 122.9(4) . . ? N3 C9 C10 130.1(4) . . ? N4 C9 C10 105.6(4) . . ? C11 C10 C15 121.1(4) . . ? C11 C10 C9 131.6(4) . . ? C15 C10 C9 107.1(4) . . ? C12 C11 C10 117.9(5) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C11 C12 C13 120.9(4) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C14 C13 C12 122.4(4) . . ? C14 C13 H13A 118.8 . . ? C12 C13 H13A 118.8 . . ? C13 C14 C15 117.1(5) . . ? C13 C14 H14A 121.5 . . ? C15 C14 H14A 121.5 . . ? C14 C15 C10 120.6(4) . . ? C14 C15 C16 131.9(4) . . ? C10 C15 C16 107.5(4) . . ? N5 C16 N4 122.5(4) . . ? N5 C16 C15 131.0(4) . . ? N4 C16 C15 105.2(4) . . ? N5 C17 N6 122.8(4) . . ? N5 C17 C18 129.8(4) . . ? N6 C17 C18 105.6(3) . . ? C19 C18 C23 120.2(4) . . ? C19 C18 C17 132.1(4) . . ? C23 C18 C17 107.1(4) . . ? C20 C19 C18 118.5(4) . . ? C20 C19 H19A 120.8 . . ? C18 C19 H19A 120.8 . . ? C19 C20 C21 121.5(4) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.0(4) . . ? C22 C21 H21A 119.5 . . ? C20 C21 H21A 119.5 . . ? C23 C22 C21 118.6(4) . . ? C23 C22 H22A 120.7 . . ? C21 C22 H22A 120.7 . . ? C22 C23 C18 120.2(4) . . ? C22 C23 C24 132.2(4) . . ? C18 C23 C24 107.1(4) . . ? N1 C24 N6 122.5(4) . . ? N1 C24 C23 129.3(4) . . ? N6 C24 C23 106.4(3) . . ? O1 C25 C30 120.8(4) . . ? O1 C25 C26 120.8(4) . . ? C30 C25 C26 118.4(4) . . ? C27 C26 C25 120.4(4) . . ? C27 C26 I1 118.7(3) . . ? C25 C26 I1 120.9(3) . . ? C28 C27 C26 120.4(4) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C29 C28 C27 119.5(4) . . ? C29 C28 H28A 120.2 . . ? C27 C28 H28A 120.2 . . ? C28 C29 C30 121.2(5) . . ? C28 C29 H29A 119.4 . . ? C30 C29 H29A 119.4 . . ? C29 C30 C25 120.0(4) . . ? C29 C30 H30A 120.0 . . ? C25 C30 H30A 120.0 . . ? O1 B1 N2 111.1(3) . . ? O1 B1 N4 116.8(4) . . ? N2 B1 N4 103.9(3) . . ? O1 B1 N6 115.9(4) . . ? N2 B1 N6 104.7(3) . . ? N4 B1 N6 103.1(3) . . ? C2S C1S C3S 120.1(5) . 3_656 ? C2S C1S H1S 119.9 . . ? C3S C1S H1S 119.9 3_656 . ? C1S C2S C3S 120.2(4) . . ? C1S C2S H2S 119.9 . . ? C3S C2S H2S 119.9 . . ? C2S C3S C1S 119.7(5) . 3_656 ? C2S C3S H3S 120.2 . . ? C1S C3S H3S 120.2 3_656 . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.477 _refine_diff_density_min -1.098 _refine_diff_density_rms 0.123 data_k11175 _database_code_depnum_ccdc_archive 'CCDC 906282' #TrackingRef '4d o-IPhO-BsubPc k11175.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Iodophenolato)(subphthalocyaninato)boron ; _chemical_name_common (2-Iodophenolato)(subphthalocyaninato)boron _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 B I N6 O' _chemical_formula_sum 'C30 H16 B I N6 O' _chemical_formula_weight 614.20 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' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0324(5) _cell_length_b 20.5587(8) _cell_length_c 11.6778(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.710(2) _cell_angle_gamma 90.00 _cell_volume 2443.31(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15379 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 1.349 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.607 _exptl_absorpt_correction_T_max 0.900 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The 101 reflection was removed as it was partially obscured by the beamstop. ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15379 _diffrn_reflns_av_R_equivalents 0.0920 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4282 _reflns_number_gt 2315 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.1655P)^2^+8.8640P] 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 4282 _refine_ls_number_parameters 326 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1609 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.3026 _refine_ls_wR_factor_gt 0.2426 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 I1 I -0.0014(5) 0.0741(3) 0.0322(4) 0.0719(13) Uani 0.432(10) 1 d PD . 1 I1A I -0.0116(4) 0.1052(4) 0.0111(6) 0.1098(19) Uani 0.568(10) 1 d PD . 2 O1 O 0.2603(5) 0.1320(2) 0.2413(5) 0.0388(13) Uani 1 1 d D . . N1 N 0.4890(6) 0.0963(3) 0.3202(6) 0.0301(15) Uani 1 1 d . . . N2 N 0.4653(6) -0.0158(3) 0.2664(6) 0.0332(15) Uani 1 1 d . . . N3 N 0.3538(6) 0.0658(3) 0.1180(6) 0.0335(15) Uani 1 1 d . . . N4 N 0.3285(6) 0.1370(3) -0.0497(6) 0.0334(15) Uani 1 1 d . . . N5 N 0.4213(6) 0.1747(3) 0.1588(5) 0.0298(15) Uani 1 1 d . . . N6 N 0.6041(6) 0.1974(3) 0.3475(6) 0.0345(16) Uani 1 1 d . . . C1 C 0.5893(8) 0.1381(4) 0.3876(7) 0.0318(18) Uani 1 1 d . . . C2 C 0.6821(8) 0.0972(4) 0.4855(7) 0.0323(18) Uani 1 1 d . . . C3 C 0.8004(8) 0.1122(4) 0.5811(7) 0.0351(19) Uani 1 1 d . . . H3A H 0.8312 0.1558 0.5959 0.042 Uiso 1 1 calc R . . C4 C 0.8725(8) 0.0618(4) 0.6546(8) 0.044(2) Uani 1 1 d . . . H4A H 0.9543 0.0708 0.7202 0.053 Uiso 1 1 calc R . . C5 C 0.8261(9) -0.0028(4) 0.6333(8) 0.042(2) Uani 1 1 d . . . H5A H 0.8752 -0.0364 0.6870 0.051 Uiso 1 1 calc R . . C6 C 0.7108(8) -0.0178(4) 0.5359(8) 0.038(2) Uani 1 1 d . . . H6A H 0.6812 -0.0616 0.5204 0.046 Uiso 1 1 calc R . . C7 C 0.6389(8) 0.0321(4) 0.4609(7) 0.0323(18) Uani 1 1 d . . . C8 C 0.5199(8) 0.0322(4) 0.3466(7) 0.0357(19) Uani 1 1 d . . . C9 C 0.3887(8) 0.0023(4) 0.1504(7) 0.0332(19) Uani 1 1 d . . . C10 C 0.3485(8) -0.0327(4) 0.0321(7) 0.0339(18) Uani 1 1 d . . . C11 C 0.3512(9) -0.0985(4) 0.0037(9) 0.043(2) Uani 1 1 d . . . H11A H 0.3868 -0.1299 0.0676 0.052 Uiso 1 1 calc R . . C12 C 0.3009(8) -0.1167(4) -0.1193(8) 0.043(2) Uani 1 1 d . . . H12A H 0.2988 -0.1615 -0.1398 0.052 Uiso 1 1 calc R . . C13 C 0.2525(8) -0.0704(4) -0.2156(8) 0.045(2) Uani 1 1 d . . . H13A H 0.2168 -0.0846 -0.2995 0.054 Uiso 1 1 calc R . . C14 C 0.2566(9) -0.0045(4) -0.1890(8) 0.042(2) Uani 1 1 d . . . H14A H 0.2289 0.0269 -0.2538 0.051 Uiso 1 1 calc R . . C15 C 0.3026(7) 0.0146(4) -0.0647(8) 0.0360(19) Uani 1 1 d . . . C16 C 0.3203(7) 0.0780(4) -0.0060(7) 0.0328(18) Uani 1 1 d . . . C17 C 0.3869(7) 0.1836(4) 0.0337(7) 0.0336(19) Uani 1 1 d . . . C18 C 0.4580(7) 0.2426(4) 0.0216(7) 0.0312(17) Uani 1 1 d . . . C19 C 0.4581(8) 0.2756(4) -0.0796(7) 0.0362(19) Uani 1 1 d . . . H19A H 0.4025 0.2629 -0.1612 0.043 Uiso 1 1 calc R . . C20 C 0.5424(9) 0.3285(4) -0.0592(8) 0.045(2) Uani 1 1 d . . . H20A H 0.5432 0.3528 -0.1280 0.055 Uiso 1 1 calc R . . C21 C 0.6260(8) 0.3465(4) 0.0611(8) 0.041(2) Uani 1 1 d . . . H21A H 0.6827 0.3828 0.0720 0.049 Uiso 1 1 calc R . . C22 C 0.6284(8) 0.3128(4) 0.1646(7) 0.0349(19) Uani 1 1 d . . . H22A H 0.6867 0.3245 0.2459 0.042 Uiso 1 1 calc R . . C23 C 0.5414(7) 0.2610(3) 0.1440(7) 0.0316(18) Uani 1 1 d . . . C24 C 0.5248(8) 0.2139(3) 0.2312(7) 0.0321(18) Uani 1 1 d . . . C25 C 0.1685(11) 0.1808(4) 0.1945(16) 0.0526(14) Uani 0.432(10) 1 d PGD . 1 C26 C 0.0435(10) 0.1648(5) 0.1101(13) 0.0526(14) Uani 0.432(10) 1 d PGD . 1 C27 C -0.0522(9) 0.2128(6) 0.0657(13) 0.0526(14) Uani 0.432(10) 1 d PGD . 1 H27A H -0.1377 0.2018 0.0080 0.063 Uiso 0.432(10) 1 calc PR . 1 C28 C -0.0228(11) 0.2767(5) 0.1055(14) 0.0526(14) Uani 0.432(10) 1 d PG . 1 H28A H -0.0882 0.3095 0.0751 0.063 Uiso 0.432(10) 1 calc PR . 1 C29 C 0.1023(13) 0.2927(4) 0.1898(14) 0.0526(14) Uani 0.432(10) 1 d PG . 1 H29A H 0.1223 0.3364 0.2170 0.063 Uiso 0.432(10) 1 calc PR . 1 C30 C 0.1979(11) 0.2447(4) 0.2343(15) 0.0526(14) Uani 0.432(10) 1 d PG . 1 H30A H 0.2834 0.2556 0.2919 0.063 Uiso 0.432(10) 1 calc PR . 1 C25A C 0.1910(9) 0.1892(3) 0.2042(12) 0.0526(14) Uani 0.568(10) 1 d PGD . 2 C26A C 0.0620(8) 0.1861(4) 0.1183(10) 0.0526(14) Uani 0.568(10) 1 d PGD . 2 C27A C -0.0175(8) 0.2410(5) 0.0936(10) 0.0526(14) Uani 0.568(10) 1 d PGD . 2 H27B H -0.1056 0.2389 0.0349 0.063 Uiso 0.568(10) 1 calc PR . 2 C28A C 0.0320(10) 0.2990(4) 0.1549(11) 0.0526(14) Uani 0.568(10) 1 d PG . 2 H28B H -0.0224 0.3366 0.1380 0.063 Uiso 0.568(10) 1 calc PR . 2 C29A C 0.1609(11) 0.3022(3) 0.2408(11) 0.0526(14) Uani 0.568(10) 1 d PG . 2 H29B H 0.1947 0.3419 0.2827 0.063 Uiso 0.568(10) 1 calc PR . 2 C30A C 0.2404(9) 0.2473(4) 0.2655(12) 0.0526(14) Uani 0.568(10) 1 d PG . 2 H30B H 0.3285 0.2494 0.3242 0.063 Uiso 0.568(10) 1 calc PR . 2 B1 B 0.3726(9) 0.1182(4) 0.2110(8) 0.033(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 I1 0.0441(14) 0.124(3) 0.0421(13) -0.0055(17) 0.0108(9) -0.0190(19) I1A 0.0447(11) 0.161(4) 0.114(3) -0.078(3) 0.0209(17) -0.017(2) O1 0.032(3) 0.039(3) 0.044(3) 0.011(2) 0.014(3) 0.005(2) N1 0.033(4) 0.038(4) 0.019(3) 0.003(3) 0.010(3) -0.005(3) N2 0.034(4) 0.035(3) 0.030(4) -0.001(3) 0.011(3) -0.005(3) N3 0.025(3) 0.041(4) 0.029(4) -0.001(3) 0.004(3) -0.005(3) N4 0.025(3) 0.047(4) 0.019(3) -0.001(3) -0.002(3) -0.002(3) N5 0.029(3) 0.038(4) 0.020(3) -0.002(3) 0.007(3) -0.002(3) N6 0.036(4) 0.040(4) 0.023(4) 0.001(3) 0.007(3) 0.002(3) C1 0.036(4) 0.037(4) 0.020(4) 0.002(3) 0.009(3) 0.000(4) C2 0.032(4) 0.043(5) 0.022(4) 0.007(3) 0.012(4) 0.003(3) C3 0.034(4) 0.037(4) 0.028(4) 0.001(3) 0.006(4) 0.000(4) C4 0.034(5) 0.059(6) 0.034(5) 0.004(4) 0.008(4) -0.001(4) C5 0.049(6) 0.044(5) 0.034(5) 0.008(4) 0.016(4) 0.010(4) C6 0.043(5) 0.036(4) 0.038(5) 0.004(4) 0.019(4) 0.000(4) C7 0.033(4) 0.039(4) 0.026(4) -0.002(3) 0.012(4) 0.000(4) C8 0.032(4) 0.045(5) 0.030(5) 0.008(4) 0.013(4) 0.004(4) C9 0.029(4) 0.039(5) 0.031(5) -0.001(3) 0.010(4) -0.005(3) C10 0.030(4) 0.041(5) 0.028(4) -0.004(4) 0.009(4) -0.013(4) C11 0.036(5) 0.046(5) 0.050(6) 0.001(4) 0.020(4) -0.003(4) C12 0.040(5) 0.045(5) 0.044(5) -0.012(4) 0.014(4) -0.002(4) C13 0.035(5) 0.067(6) 0.038(5) -0.014(5) 0.020(4) -0.016(4) C14 0.037(5) 0.058(6) 0.029(5) -0.004(4) 0.009(4) -0.008(4) C15 0.019(4) 0.052(5) 0.034(5) -0.007(4) 0.007(4) -0.008(3) C16 0.027(4) 0.043(5) 0.024(4) 0.003(3) 0.005(3) -0.005(3) C17 0.024(4) 0.047(5) 0.028(5) 0.009(4) 0.009(3) 0.003(3) C18 0.024(4) 0.040(4) 0.027(4) 0.003(3) 0.008(3) 0.003(3) C19 0.032(4) 0.045(5) 0.025(4) 0.005(4) 0.004(4) 0.001(4) C20 0.058(6) 0.044(5) 0.038(5) 0.009(4) 0.022(5) 0.000(4) C21 0.039(5) 0.043(5) 0.041(5) 0.007(4) 0.017(4) -0.003(4) C22 0.033(4) 0.041(4) 0.028(4) 0.003(3) 0.009(4) 0.002(4) C23 0.030(4) 0.033(4) 0.028(4) 0.003(3) 0.006(3) 0.001(3) C24 0.038(4) 0.034(4) 0.025(4) -0.003(3) 0.013(4) 0.003(3) C25 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C26 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C27 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C28 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C29 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C30 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C25A 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C26A 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C27A 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C28A 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C29A 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) C30A 0.039(3) 0.078(4) 0.043(4) 0.003(3) 0.018(3) -0.012(3) B1 0.029(5) 0.038(5) 0.029(5) 0.004(4) 0.006(4) -0.005(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 I1 C26 2.051(7) . ? I1 I1 3.141(13) 3 ? I1A C26A 2.050(7) . ? O1 C25A 1.378(7) . ? O1 C25 1.379(7) . ? O1 B1 1.442(11) . ? N1 C8 1.366(10) . ? N1 C1 1.381(10) . ? N1 B1 1.488(11) . ? N2 C8 1.334(10) . ? N2 C9 1.343(10) . ? N3 C16 1.372(10) . ? N3 C9 1.372(10) . ? N3 B1 1.487(11) . ? N4 C16 1.333(10) . ? N4 C17 1.339(10) . ? N5 C17 1.373(10) . ? N5 C24 1.386(10) . ? N5 B1 1.503(11) . ? N6 C1 1.339(9) . ? N6 C24 1.344(9) . ? C1 C2 1.469(10) . ? C2 C3 1.386(11) . ? C2 C7 1.412(11) . ? C3 C4 1.384(11) . ? C3 H3A 0.9500 . ? C4 C5 1.409(12) . ? C4 H4A 0.9500 . ? C5 C6 1.375(12) . ? C5 H5A 0.9500 . ? C6 C7 1.384(11) . ? C6 H6A 0.9500 . ? C7 C8 1.467(11) . ? C9 C10 1.467(11) . ? C10 C11 1.395(11) . ? C10 C15 1.429(12) . ? C11 C12 1.377(12) . ? C11 H11A 0.9500 . ? C12 C13 1.411(13) . ? C12 H12A 0.9500 . ? C13 C14 1.388(12) . ? C13 H13A 0.9500 . ? C14 C15 1.397(12) . ? C14 H14A 0.9500 . ? C15 C16 1.449(11) . ? C17 C18 1.481(11) . ? C18 C19 1.363(11) . ? C18 C23 1.421(10) . ? C19 C20 1.390(12) . ? C19 H19A 0.9500 . ? C20 C21 1.401(12) . ? C20 H20A 0.9500 . ? C21 C22 1.384(11) . ? C21 H21A 0.9500 . ? C22 C23 1.391(11) . ? C22 H22A 0.9500 . ? C23 C24 1.468(11) . ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C27 H27A 0.9500 . ? C28 C29 1.3900 . ? C28 H28A 0.9500 . ? C29 C30 1.3900 . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C25A C26A 1.3900 . ? C25A C30A 1.3900 . ? C26A C27A 1.3900 . ? C27A C28A 1.3900 . ? C27A H27B 0.9500 . ? C28A C29A 1.3900 . ? C28A H28B 0.9500 . ? C29A C30A 1.3900 . ? C29A H29B 0.9500 . ? C30A H30B 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 C26 I1 I1 164.9(3) . 3 ? C25A O1 C25 12.0(6) . . ? C25A O1 B1 121.1(8) . . ? C25 O1 B1 127.9(11) . . ? C8 N1 C1 113.3(6) . . ? C8 N1 B1 122.9(6) . . ? C1 N1 B1 122.5(6) . . ? C8 N2 C9 116.1(6) . . ? C16 N3 C9 113.4(6) . . ? C16 N3 B1 122.9(6) . . ? C9 N3 B1 122.9(7) . . ? C16 N4 C17 117.2(6) . . ? C17 N5 C24 113.3(6) . . ? C17 N5 B1 122.6(6) . . ? C24 N5 B1 122.7(6) . . ? C1 N6 C24 117.5(6) . . ? N6 C1 N1 123.1(6) . . ? N6 C1 C2 130.6(7) . . ? N1 C1 C2 104.6(6) . . ? C3 C2 C7 120.9(7) . . ? C3 C2 C1 131.1(7) . . ? C7 C2 C1 107.8(7) . . ? C4 C3 C2 118.1(7) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 120.9(8) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C6 C5 C4 121.0(8) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C5 C6 C7 118.5(8) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C6 C7 C2 120.6(7) . . ? C6 C7 C8 132.0(7) . . ? C2 C7 C8 107.3(7) . . ? N2 C8 N1 123.4(7) . . ? N2 C8 C7 129.8(7) . . ? N1 C8 C7 105.3(7) . . ? N2 C9 N3 122.8(7) . . ? N2 C9 C10 131.1(7) . . ? N3 C9 C10 104.9(7) . . ? C11 C10 C15 120.4(8) . . ? C11 C10 C9 132.3(8) . . ? C15 C10 C9 107.2(6) . . ? C12 C11 C10 118.3(8) . . ? C12 C11 H11A 120.8 . . ? C10 C11 H11A 120.8 . . ? C11 C12 C13 121.6(8) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C14 C13 C12 120.8(8) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 118.3(8) . . ? C13 C14 H14A 120.8 . . ? C15 C14 H14A 120.8 . . ? C14 C15 C10 120.4(7) . . ? C14 C15 C16 132.3(8) . . ? C10 C15 C16 107.3(7) . . ? N4 C16 N3 122.6(7) . . ? N4 C16 C15 130.8(7) . . ? N3 C16 C15 105.5(6) . . ? N4 C17 N5 122.4(7) . . ? N4 C17 C18 129.8(7) . . ? N5 C17 C18 105.7(6) . . ? C19 C18 C23 121.5(7) . . ? C19 C18 C17 132.0(7) . . ? C23 C18 C17 106.5(7) . . ? C18 C19 C20 117.8(7) . . ? C18 C19 H19A 121.1 . . ? C20 C19 H19A 121.1 . . ? C19 C20 C21 121.1(8) . . ? C19 C20 H20A 119.4 . . ? C21 C20 H20A 119.4 . . ? C22 C21 C20 121.8(8) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C23 116.9(7) . . ? C21 C22 H22A 121.5 . . ? C23 C22 H22A 121.5 . . ? C22 C23 C18 120.9(7) . . ? C22 C23 C24 130.4(7) . . ? C18 C23 C24 108.4(6) . . ? N6 C24 N5 122.1(7) . . ? N6 C24 C23 131.3(7) . . ? N5 C24 C23 104.8(6) . . ? O1 C25 C26 119.0(6) . . ? O1 C25 C30 120.9(6) . . ? C26 C25 C30 120.0 . . ? C25 C26 C27 120.0 . . ? C25 C26 I1 122.2(4) . . ? C27 C26 I1 117.5(4) . . ? C26 C27 C28 120.0 . . ? C26 C27 H27A 120.0 . . ? C28 C27 H27A 120.0 . . ? C29 C28 C27 120.0 . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C28 C29 C30 120.0 . . ? C28 C29 H29A 120.0 . . ? C30 C29 H29A 120.0 . . ? C29 C30 C25 120.0 . . ? C29 C30 H30A 120.0 . . ? C25 C30 H30A 120.0 . . ? O1 C25A C26A 118.5(6) . . ? O1 C25A C30A 120.7(6) . . ? C26A C25A C30A 120.0 . . ? C25A C26A C27A 120.0 . . ? C25A C26A I1A 122.1(4) . . ? C27A C26A I1A 117.5(4) . . ? C26A C27A C28A 120.0 . . ? C26A C27A H27B 120.0 . . ? C28A C27A H27B 120.0 . . ? C29A C28A C27A 120.0 . . ? C29A C28A H28B 120.0 . . ? C27A C28A H28B 120.0 . . ? C30A C29A C28A 120.0 . . ? C30A C29A H29B 120.0 . . ? C28A C29A H29B 120.0 . . ? C29A C30A C25A 120.0 . . ? C29A C30A H30B 120.0 . . ? C25A C30A H30B 120.0 . . ? O1 B1 N3 115.5(7) . . ? O1 B1 N1 112.8(7) . . ? N3 B1 N1 103.7(6) . . ? O1 B1 N5 115.0(7) . . ? N3 B1 N5 103.6(7) . . ? N1 B1 N5 104.8(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.627 _refine_diff_density_min -1.298 _refine_diff_density_rms 0.147 data_k11121 _database_code_depnum_ccdc_archive 'CCDC 906283' #TrackingRef '4e Cl5PhO-BsubPc k11121.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Pentachlorophenolato)(subphthalocyaninato)boron ; _chemical_name_common ; Cl5-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H12 B Cl5 N6 O' _chemical_formula_sum 'C30 H12 B Cl5 N6 O' _chemical_formula_weight 660.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5099(3) _cell_length_b 12.5191(4) _cell_length_c 13.8756(6) _cell_angle_alpha 107.637(2) _cell_angle_beta 100.015(2) _cell_angle_gamma 99.280(3) _cell_volume 1350.77(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 17295 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.577 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.750 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17295 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0953 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6109 _reflns_number_gt 3387 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0984P)^2^] 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 6109 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1322 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1477 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 Cl1 Cl 1.00460(13) 0.36220(8) 1.01469(8) 0.0419(3) Uani 1 1 d . . . Cl2 Cl 1.03242(14) 0.20809(10) 1.15403(8) 0.0549(3) Uani 1 1 d . . . Cl3 Cl 0.79729(14) -0.03441(9) 1.08176(8) 0.0456(3) Uani 1 1 d . . . Cl4 Cl 0.53616(13) -0.12144(8) 0.87114(8) 0.0419(3) Uani 1 1 d . . . Cl5 Cl 0.51239(11) 0.03435(8) 0.73216(7) 0.0345(3) Uani 1 1 d . . . O1 O 0.7548(3) 0.25367(19) 0.81625(19) 0.0257(6) Uani 1 1 d . . . N1 N 0.7724(3) 0.2922(2) 0.6557(2) 0.0252(7) Uani 1 1 d . . . N2 N 0.9685(3) 0.4717(2) 0.7204(2) 0.0261(7) Uani 1 1 d . . . N3 N 1.0203(3) 0.3149(2) 0.7739(2) 0.0238(7) Uani 1 1 d . . . N4 N 1.1374(3) 0.1537(2) 0.7655(2) 0.0250(7) Uani 1 1 d . . . N5 N 0.8615(3) 0.1295(2) 0.6763(2) 0.0236(7) Uani 1 1 d . . . N6 N 0.6569(3) 0.1067(2) 0.5271(2) 0.0273(7) Uani 1 1 d . . . C1 C 0.6723(4) 0.2213(3) 0.5609(3) 0.0271(8) Uani 1 1 d . . . C2 C 0.6314(4) 0.2960(3) 0.5037(3) 0.0275(8) Uani 1 1 d . . . C3 C 0.5320(4) 0.2746(3) 0.4058(3) 0.0316(9) Uani 1 1 d . . . H3A H 0.4656 0.2000 0.3664 0.038 Uiso 1 1 calc R . . C4 C 0.5320(5) 0.3639(3) 0.3675(3) 0.0401(10) Uani 1 1 d . . . H4A H 0.4623 0.3512 0.3018 0.048 Uiso 1 1 calc R . . C5 C 0.6327(5) 0.4727(3) 0.4234(3) 0.0365(10) Uani 1 1 d . . . H5A H 0.6315 0.5322 0.3942 0.044 Uiso 1 1 calc R . . C6 C 0.7335(5) 0.4965(3) 0.5197(3) 0.0353(10) Uani 1 1 d . . . H6A H 0.8028 0.5707 0.5566 0.042 Uiso 1 1 calc R . . C7 C 0.7309(4) 0.4079(3) 0.5618(3) 0.0282(9) Uani 1 1 d . . . C8 C 0.8277(4) 0.4018(3) 0.6561(3) 0.0265(8) Uani 1 1 d . . . C9 C 1.0661(4) 0.4256(3) 0.7747(3) 0.0236(8) Uani 1 1 d . . . C10 C 1.2419(4) 0.4610(3) 0.8192(3) 0.0284(8) Uani 1 1 d . . . C11 C 1.3563(4) 0.5637(3) 0.8422(3) 0.0323(9) Uani 1 1 d . . . H11A H 1.3224 0.6302 0.8354 0.039 Uiso 1 1 calc R . . C12 C 1.5209(5) 0.5663(3) 0.8753(3) 0.0376(10) Uani 1 1 d . . . H12A H 1.6003 0.6360 0.8926 0.045 Uiso 1 1 calc R . . C13 C 1.5713(5) 0.4682(3) 0.8835(3) 0.0405(10) Uani 1 1 d . . . H13A H 1.6850 0.4720 0.9045 0.049 Uiso 1 1 calc R . . C14 C 1.4609(4) 0.3659(3) 0.8621(3) 0.0315(9) Uani 1 1 d . . . H14A H 1.4967 0.2998 0.8684 0.038 Uiso 1 1 calc R . . C15 C 1.2944(4) 0.3624(3) 0.8308(3) 0.0251(8) Uani 1 1 d . . . C16 C 1.1501(4) 0.2686(3) 0.7956(3) 0.0251(8) Uani 1 1 d . . . C17 C 0.9958(4) 0.0869(3) 0.7017(3) 0.0234(8) Uani 1 1 d . . . C18 C 0.9601(4) -0.0298(3) 0.6267(3) 0.0254(8) Uani 1 1 d . . . C19 C 1.0463(4) -0.1166(3) 0.6160(3) 0.0295(9) Uani 1 1 d . . . H19A H 1.1450 -0.1070 0.6651 0.035 Uiso 1 1 calc R . . C20 C 0.9838(5) -0.2179(3) 0.5313(3) 0.0339(10) Uani 1 1 d . . . H20A H 1.0373 -0.2798 0.5243 0.041 Uiso 1 1 calc R . . C21 C 0.8433(5) -0.2297(3) 0.4564(3) 0.0326(9) Uani 1 1 d . . . H21A H 0.8050 -0.2992 0.3985 0.039 Uiso 1 1 calc R . . C22 C 0.7582(4) -0.1435(3) 0.4638(3) 0.0307(9) Uani 1 1 d . . . H22A H 0.6647 -0.1518 0.4112 0.037 Uiso 1 1 calc R . . C23 C 0.8149(4) -0.0438(3) 0.5514(3) 0.0256(8) Uani 1 1 d . . . C24 C 0.7600(4) 0.0635(3) 0.5818(3) 0.0258(8) Uani 1 1 d . . . C25 C 0.7674(4) 0.1865(3) 0.8770(3) 0.0273(8) Uani 1 1 d . . . C26 C 0.8792(4) 0.2261(3) 0.9734(3) 0.0304(9) Uani 1 1 d . . . C27 C 0.8903(5) 0.1581(3) 1.0364(3) 0.0352(9) Uani 1 1 d . . . C28 C 0.7856(5) 0.0498(3) 1.0045(3) 0.0352(9) Uani 1 1 d . . . C29 C 0.6695(5) 0.0113(3) 0.9102(3) 0.0306(9) Uani 1 1 d . . . C30 C 0.6593(4) 0.0786(3) 0.8469(3) 0.0281(8) Uani 1 1 d . . . B1 B 0.8480(5) 0.2470(3) 0.7363(3) 0.0254(9) 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 Cl1 0.0478(6) 0.0357(6) 0.0331(6) 0.0056(4) 0.0102(5) -0.0041(4) Cl2 0.0606(7) 0.0642(8) 0.0325(6) 0.0174(6) -0.0006(5) 0.0054(6) Cl3 0.0637(7) 0.0465(6) 0.0404(6) 0.0273(5) 0.0180(5) 0.0200(5) Cl4 0.0525(6) 0.0318(5) 0.0436(6) 0.0175(5) 0.0168(5) 0.0009(4) Cl5 0.0299(5) 0.0371(5) 0.0356(6) 0.0157(4) 0.0058(4) 0.0012(4) O1 0.0307(13) 0.0228(12) 0.0311(14) 0.0130(11) 0.0163(11) 0.0100(10) N1 0.0258(15) 0.0227(15) 0.0305(18) 0.0116(13) 0.0095(13) 0.0074(12) N2 0.0258(16) 0.0247(15) 0.0279(17) 0.0084(13) 0.0081(13) 0.0051(13) N3 0.0265(15) 0.0231(15) 0.0254(16) 0.0105(13) 0.0085(13) 0.0087(12) N4 0.0274(16) 0.0266(16) 0.0266(17) 0.0124(13) 0.0092(13) 0.0118(13) N5 0.0258(15) 0.0195(15) 0.0266(17) 0.0077(13) 0.0085(13) 0.0061(12) N6 0.0259(16) 0.0237(16) 0.0348(18) 0.0116(14) 0.0112(14) 0.0050(12) C1 0.0234(18) 0.0270(19) 0.033(2) 0.0115(17) 0.0075(16) 0.0073(15) C2 0.0267(19) 0.0273(19) 0.033(2) 0.0144(17) 0.0097(16) 0.0071(15) C3 0.037(2) 0.027(2) 0.031(2) 0.0102(17) 0.0097(18) 0.0065(16) C4 0.047(2) 0.039(2) 0.038(2) 0.016(2) 0.009(2) 0.0132(19) C5 0.046(2) 0.031(2) 0.039(2) 0.0204(19) 0.010(2) 0.0118(18) C6 0.036(2) 0.030(2) 0.043(3) 0.0158(19) 0.0112(19) 0.0084(17) C7 0.0262(19) 0.0282(19) 0.035(2) 0.0135(17) 0.0124(17) 0.0069(15) C8 0.0273(19) 0.0233(18) 0.035(2) 0.0134(16) 0.0146(17) 0.0092(15) C9 0.0267(19) 0.0222(18) 0.0237(19) 0.0083(15) 0.0090(15) 0.0062(14) C10 0.032(2) 0.029(2) 0.023(2) 0.0079(16) 0.0099(16) 0.0020(16) C11 0.036(2) 0.028(2) 0.030(2) 0.0106(17) 0.0052(17) 0.0009(16) C12 0.032(2) 0.036(2) 0.045(3) 0.0155(19) 0.0102(19) 0.0022(17) C13 0.029(2) 0.046(3) 0.047(3) 0.017(2) 0.0093(19) 0.0064(18) C14 0.032(2) 0.033(2) 0.032(2) 0.0127(17) 0.0108(17) 0.0103(17) C15 0.0261(18) 0.0243(18) 0.026(2) 0.0071(15) 0.0096(15) 0.0073(14) C16 0.0287(19) 0.0234(18) 0.026(2) 0.0112(15) 0.0076(16) 0.0056(15) C17 0.0261(18) 0.0202(17) 0.030(2) 0.0133(15) 0.0102(16) 0.0072(14) C18 0.0301(19) 0.0234(18) 0.027(2) 0.0119(16) 0.0131(16) 0.0045(15) C19 0.031(2) 0.026(2) 0.039(2) 0.0146(17) 0.0168(17) 0.0095(16) C20 0.040(2) 0.025(2) 0.046(3) 0.0143(18) 0.025(2) 0.0093(17) C21 0.040(2) 0.026(2) 0.035(2) 0.0094(17) 0.0179(19) 0.0068(17) C22 0.035(2) 0.028(2) 0.031(2) 0.0109(17) 0.0143(17) 0.0022(16) C23 0.032(2) 0.0200(18) 0.029(2) 0.0117(16) 0.0131(16) 0.0046(15) C24 0.0233(18) 0.0227(18) 0.036(2) 0.0162(16) 0.0093(16) 0.0024(14) C25 0.029(2) 0.029(2) 0.029(2) 0.0111(17) 0.0141(17) 0.0120(15) C26 0.031(2) 0.029(2) 0.030(2) 0.0070(17) 0.0112(17) 0.0039(16) C27 0.040(2) 0.038(2) 0.028(2) 0.0115(18) 0.0087(18) 0.0088(18) C28 0.044(2) 0.040(2) 0.032(2) 0.0194(19) 0.0160(19) 0.0182(19) C29 0.037(2) 0.0284(19) 0.032(2) 0.0128(17) 0.0172(18) 0.0080(16) C30 0.0254(19) 0.029(2) 0.036(2) 0.0150(17) 0.0150(17) 0.0095(15) B1 0.019(2) 0.028(2) 0.027(2) 0.0080(18) 0.0064(17) 0.0035(16) _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 Cl1 C26 1.726(3) . ? Cl2 C27 1.723(4) . ? Cl3 C28 1.718(4) . ? Cl4 C29 1.725(4) . ? Cl5 C30 1.719(4) . ? O1 C25 1.362(4) . ? O1 B1 1.462(5) . ? N1 C8 1.374(4) . ? N1 C1 1.380(4) . ? N1 B1 1.495(5) . ? N2 C9 1.338(4) . ? N2 C8 1.347(4) . ? N3 C16 1.357(4) . ? N3 C9 1.374(4) . ? N3 B1 1.486(5) . ? N4 C17 1.338(4) . ? N4 C16 1.351(4) . ? N5 C24 1.366(4) . ? N5 C17 1.373(4) . ? N5 B1 1.489(5) . ? N6 C1 1.344(4) . ? N6 C24 1.345(4) . ? C1 C2 1.445(5) . ? C2 C3 1.392(5) . ? C2 C7 1.423(5) . ? C3 C4 1.376(5) . ? C3 H3A 0.9500 . ? C4 C5 1.394(5) . ? C4 H4A 0.9500 . ? C5 C6 1.374(5) . ? C5 H5A 0.9500 . ? C6 C7 1.400(5) . ? C6 H6A 0.9500 . ? C7 C8 1.450(5) . ? C9 C10 1.454(5) . ? C10 C11 1.393(5) . ? C10 C15 1.422(5) . ? C11 C12 1.388(5) . ? C11 H11A 0.9500 . ? C12 C13 1.394(6) . ? C12 H12A 0.9500 . ? C13 C14 1.376(5) . ? C13 H13A 0.9500 . ? C14 C15 1.397(5) . ? C14 H14A 0.9500 . ? C15 C16 1.451(4) . ? C17 C18 1.462(5) . ? C18 C19 1.392(5) . ? C18 C23 1.421(5) . ? C19 C20 1.390(5) . ? C19 H19A 0.9500 . ? C20 C21 1.395(5) . ? C20 H20A 0.9500 . ? C21 C22 1.382(5) . ? C21 H21A 0.9500 . ? C22 C23 1.397(5) . ? C22 H22A 0.9500 . ? C23 C24 1.458(5) . ? C25 C26 1.394(5) . ? C25 C30 1.403(5) . ? C26 C27 1.395(5) . ? C27 C28 1.392(5) . ? C28 C29 1.391(5) . ? C29 C30 1.391(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 B1 121.1(3) . . ? C8 N1 C1 112.1(3) . . ? C8 N1 B1 123.1(3) . . ? C1 N1 B1 122.7(3) . . ? C9 N2 C8 117.3(3) . . ? C16 N3 C9 112.9(3) . . ? C16 N3 B1 123.3(3) . . ? C9 N3 B1 123.1(3) . . ? C17 N4 C16 116.7(3) . . ? C24 N5 C17 113.2(3) . . ? C24 N5 B1 123.7(3) . . ? C17 N5 B1 122.0(3) . . ? C1 N6 C24 117.6(3) . . ? N6 C1 N1 122.3(3) . . ? N6 C1 C2 129.8(3) . . ? N1 C1 C2 106.0(3) . . ? C3 C2 C7 120.3(3) . . ? C3 C2 C1 132.4(3) . . ? C7 C2 C1 107.0(3) . . ? C4 C3 C2 118.5(3) . . ? C4 C3 H3A 120.8 . . ? C2 C3 H3A 120.8 . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C6 C5 C4 121.9(4) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C7 117.9(3) . . ? C5 C6 H6A 121.0 . . ? C7 C6 H6A 121.0 . . ? C6 C7 C2 120.3(3) . . ? C6 C7 C8 131.8(3) . . ? C2 C7 C8 107.6(3) . . ? N2 C8 N1 122.4(3) . . ? N2 C8 C7 130.1(3) . . ? N1 C8 C7 105.7(3) . . ? N2 C9 N3 122.3(3) . . ? N2 C9 C10 130.1(3) . . ? N3 C9 C10 105.6(3) . . ? C11 C10 C15 120.1(3) . . ? C11 C10 C9 132.6(4) . . ? C15 C10 C9 107.1(3) . . ? C12 C11 C10 118.4(4) . . ? C12 C11 H11A 120.8 . . ? C10 C11 H11A 120.8 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C14 C13 C12 121.8(4) . . ? C14 C13 H13A 119.1 . . ? C12 C13 H13A 119.1 . . ? C13 C14 C15 118.0(4) . . ? C13 C14 H14A 121.0 . . ? C15 C14 H14A 121.0 . . ? C14 C15 C10 120.7(3) . . ? C14 C15 C16 131.9(3) . . ? C10 C15 C16 107.2(3) . . ? N4 C16 N3 122.3(3) . . ? N4 C16 C15 130.0(3) . . ? N3 C16 C15 106.2(3) . . ? N4 C17 N5 122.8(3) . . ? N4 C17 C18 130.3(3) . . ? N5 C17 C18 105.1(3) . . ? C19 C18 C23 120.6(3) . . ? C19 C18 C17 131.8(3) . . ? C23 C18 C17 107.4(3) . . ? C20 C19 C18 118.0(4) . . ? C20 C19 H19A 121.0 . . ? C18 C19 H19A 121.0 . . ? C19 C20 C21 120.9(4) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C22 C21 C20 122.1(3) . . ? C22 C21 H21A 118.9 . . ? C20 C21 H21A 118.9 . . ? C21 C22 C23 117.5(4) . . ? C21 C22 H22A 121.2 . . ? C23 C22 H22A 121.2 . . ? C22 C23 C18 120.7(3) . . ? C22 C23 C24 132.0(3) . . ? C18 C23 C24 107.1(3) . . ? N6 C24 N5 122.0(3) . . ? N6 C24 C23 131.1(3) . . ? N5 C24 C23 105.7(3) . . ? O1 C25 C26 121.2(3) . . ? O1 C25 C30 120.3(3) . . ? C26 C25 C30 118.4(3) . . ? C25 C26 C27 121.2(3) . . ? C25 C26 Cl1 118.8(3) . . ? C27 C26 Cl1 120.0(3) . . ? C28 C27 C26 120.0(4) . . ? C28 C27 Cl2 119.8(3) . . ? C26 C27 Cl2 120.2(3) . . ? C29 C28 C27 119.3(4) . . ? C29 C28 Cl3 120.3(3) . . ? C27 C28 Cl3 120.4(3) . . ? C28 C29 C30 120.8(3) . . ? C28 C29 Cl4 119.7(3) . . ? C30 C29 Cl4 119.4(3) . . ? C29 C30 C25 120.3(3) . . ? C29 C30 Cl5 121.4(3) . . ? C25 C30 Cl5 118.3(3) . . ? O1 B1 N3 115.5(3) . . ? O1 B1 N5 115.9(3) . . ? N3 B1 N5 104.0(3) . . ? O1 B1 N1 111.3(3) . . ? N3 B1 N1 104.3(3) . . ? N5 B1 N1 104.7(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.491 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.100 data_k1186 _database_code_depnum_ccdc_archive 'CCDC 906284' #TrackingRef '4f Br5PhO-BsubPc solvate k1186.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Pentabromophenolato)(subphthalocyaninato)boron ; _chemical_name_common (Pentabromophenolato)(subphthalocyaninato)boron _chemical_melting_point ? _chemical_formula_moiety 'C30 H12 B Br5 N6 O, 0.5(C6 H6)' _chemical_formula_sum 'C33 H15 B Br5 N6 O' _chemical_formula_weight 921.87 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' B B 0.0013 0.0007 '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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0395(3) _cell_length_b 11.7114(4) _cell_length_c 13.1600(4) _cell_angle_alpha 115.1770(18) _cell_angle_beta 94.9400(19) _cell_angle_gamma 93.6730(17) _cell_volume 1524.47(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15993 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 886 _exptl_absorpt_coefficient_mu 6.631 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.439 _exptl_absorpt_correction_T_max 0.603 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 15993 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.58 _reflns_number_total 6925 _reflns_number_gt 5374 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0652P)^2^] 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 6925 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Br1 Br 1.04095(4) 0.33327(4) 0.43589(4) 0.02771(12) Uani 1 1 d . . . Br2 Br 1.22751(3) 0.11126(4) 0.33914(4) 0.02868(12) Uani 1 1 d . . . Br3 Br 1.13517(4) -0.18184(4) 0.29638(4) 0.03326(13) Uani 1 1 d . . . Br4 Br 0.85031(4) -0.25323(4) 0.32678(3) 0.02562(12) Uani 1 1 d . . . Br5 Br 0.66056(4) -0.03130(4) 0.39513(4) 0.02839(12) Uani 1 1 d . . . O1 O 0.7812(2) 0.2162(2) 0.4085(2) 0.0216(6) Uani 1 1 d . . . N1 N 0.6415(3) 0.3247(3) 0.3343(3) 0.0195(7) Uani 1 1 d . . . N2 N 0.7773(3) 0.4726(3) 0.3077(3) 0.0213(7) Uani 1 1 d . . . N3 N 0.8126(3) 0.2559(3) 0.2389(3) 0.0204(7) Uani 1 1 d . . . N4 N 0.8028(3) 0.0439(3) 0.0953(3) 0.0239(8) Uani 1 1 d . . . N5 N 0.6517(3) 0.1060(3) 0.2206(3) 0.0198(7) Uani 1 1 d . . . N6 N 0.4614(3) 0.1769(3) 0.2760(3) 0.0230(7) Uani 1 1 d . . . C1 C 0.5176(3) 0.2964(4) 0.3256(3) 0.0221(9) Uani 1 1 d . . . C2 C 0.4664(3) 0.4158(4) 0.3520(3) 0.0211(8) Uani 1 1 d . . . C3 C 0.3463(4) 0.4458(4) 0.3582(3) 0.0254(9) Uani 1 1 d . . . H3A H 0.2804 0.3836 0.3469 0.030 Uiso 1 1 calc R . . C4 C 0.3263(4) 0.5702(4) 0.3816(4) 0.0298(10) Uani 1 1 d . . . H4A H 0.2452 0.5930 0.3853 0.036 Uiso 1 1 calc R . . C5 C 0.4228(4) 0.6619(4) 0.3996(4) 0.0285(10) Uani 1 1 d . . . H5A H 0.4062 0.7469 0.4192 0.034 Uiso 1 1 calc R . . C6 C 0.5421(4) 0.6333(4) 0.3900(3) 0.0252(9) Uani 1 1 d . . . H6A H 0.6067 0.6958 0.3991 0.030 Uiso 1 1 calc R . . C7 C 0.5644(4) 0.5082(4) 0.3662(3) 0.0219(8) Uani 1 1 d . . . C8 C 0.6745(3) 0.4434(3) 0.3436(3) 0.0197(8) Uani 1 1 d . . . C9 C 0.8430(3) 0.3775(4) 0.2510(3) 0.0213(8) Uani 1 1 d . . . C10 C 0.9322(3) 0.3680(4) 0.1743(3) 0.0232(9) Uani 1 1 d . . . C11 C 0.9988(4) 0.4552(4) 0.1511(4) 0.0295(10) Uani 1 1 d . . . H11A H 0.9946 0.5436 0.1934 0.035 Uiso 1 1 calc R . . C12 C 1.0718(4) 0.4126(4) 0.0653(4) 0.0347(11) Uani 1 1 d . . . H12A H 1.1183 0.4728 0.0493 0.042 Uiso 1 1 calc R . . C13 C 1.0791(4) 0.2833(4) 0.0012(4) 0.0344(11) Uani 1 1 d . . . H13A H 1.1301 0.2571 -0.0575 0.041 Uiso 1 1 calc R . . C14 C 1.0134(4) 0.1940(4) 0.0221(4) 0.0302(10) Uani 1 1 d . . . H14A H 1.0182 0.1061 -0.0217 0.036 Uiso 1 1 calc R . . C15 C 0.9394(3) 0.2347(4) 0.1091(3) 0.0233(9) Uani 1 1 d . . . C16 C 0.8558(3) 0.1656(4) 0.1471(3) 0.0216(8) Uani 1 1 d . . . C17 C 0.6974(4) 0.0189(3) 0.1292(3) 0.0217(8) Uani 1 1 d . . . C18 C 0.5972(4) -0.0808(4) 0.0703(3) 0.0240(9) Uani 1 1 d . . . C19 C 0.5887(4) -0.1950(4) -0.0281(3) 0.0288(10) Uani 1 1 d . . . H19A H 0.6574 -0.2209 -0.0678 0.035 Uiso 1 1 calc R . . C20 C 0.4772(4) -0.2682(4) -0.0651(3) 0.0310(10) Uani 1 1 d . . . H20A H 0.4695 -0.3468 -0.1307 0.037 Uiso 1 1 calc R . . C21 C 0.3745(4) -0.2296(4) -0.0083(3) 0.0305(10) Uani 1 1 d . . . H21A H 0.2995 -0.2834 -0.0356 0.037 Uiso 1 1 calc R . . C22 C 0.3801(4) -0.1158(4) 0.0856(4) 0.0291(10) Uani 1 1 d . . . H22A H 0.3095 -0.0888 0.1218 0.035 Uiso 1 1 calc R . . C23 C 0.4921(4) -0.0412(4) 0.1264(3) 0.0249(9) Uani 1 1 d . . . C24 C 0.5298(3) 0.0841(4) 0.2185(3) 0.0215(8) Uani 1 1 d . . . C25 C 0.8618(3) 0.1280(4) 0.3910(3) 0.0214(8) Uani 1 1 d . . . C26 C 0.9856(4) 0.1605(4) 0.3903(3) 0.0220(8) Uani 1 1 d . . . C27 C 1.0667(3) 0.0676(4) 0.3591(3) 0.0237(9) Uani 1 1 d . . . C28 C 1.0257(3) -0.0554(4) 0.3385(3) 0.0235(9) Uani 1 1 d . . . C29 C 0.9049(3) -0.0876(4) 0.3488(3) 0.0223(8) Uani 1 1 d . . . C30 C 0.8244(3) 0.0057(4) 0.3756(3) 0.0220(8) Uani 1 1 d . . . B1 B 0.7268(4) 0.2248(4) 0.3065(4) 0.0223(10) Uani 1 1 d . . . C1S C 0.5380(5) 0.5895(5) 0.1096(4) 0.0420(12) Uani 1 1 d . . . H1S H 0.5644 0.6512 0.1849 0.050 Uiso 1 1 calc R . . C2S C 0.6216(5) 0.5436(5) 0.0349(4) 0.0403(12) Uani 1 1 d . . . H2SA H 0.7059 0.5736 0.0591 0.048 Uiso 1 1 calc R . . C3S C 0.5853(5) 0.4545(5) -0.0752(4) 0.0444(13) Uani 1 1 d . . . H3S H 0.6439 0.4237 -0.1266 0.053 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 0.0210(2) 0.0188(2) 0.0386(2) 0.00923(18) -0.00078(17) -0.00122(15) Br2 0.0155(2) 0.0258(2) 0.0420(3) 0.01176(19) 0.00615(16) 0.00132(15) Br3 0.0216(2) 0.0235(2) 0.0505(3) 0.0106(2) 0.00859(18) 0.00720(16) Br4 0.0219(2) 0.0181(2) 0.0353(2) 0.00979(18) 0.00539(16) 0.00156(15) Br5 0.0183(2) 0.0273(2) 0.0436(3) 0.0179(2) 0.00990(17) 0.00339(16) O1 0.0180(14) 0.0172(13) 0.0255(14) 0.0047(12) 0.0052(11) 0.0040(10) N1 0.0169(16) 0.0164(16) 0.0238(16) 0.0068(14) 0.0047(12) 0.0033(12) N2 0.0171(16) 0.0189(16) 0.0256(17) 0.0071(14) 0.0047(13) 0.0018(12) N3 0.0170(16) 0.0182(16) 0.0237(16) 0.0067(14) 0.0038(13) 0.0023(12) N4 0.0187(17) 0.0221(17) 0.0290(18) 0.0079(15) 0.0076(13) 0.0058(13) N5 0.0158(16) 0.0148(15) 0.0266(17) 0.0067(14) 0.0045(12) 0.0012(12) N6 0.0193(17) 0.0173(16) 0.0294(18) 0.0066(15) 0.0073(13) 0.0005(13) C1 0.0153(19) 0.021(2) 0.027(2) 0.0074(17) 0.0071(15) 0.0040(15) C2 0.021(2) 0.0151(18) 0.0240(19) 0.0044(16) 0.0055(15) 0.0040(15) C3 0.021(2) 0.023(2) 0.032(2) 0.0098(18) 0.0078(16) 0.0063(16) C4 0.022(2) 0.030(2) 0.035(2) 0.010(2) 0.0103(17) 0.0118(17) C5 0.032(2) 0.019(2) 0.034(2) 0.0098(19) 0.0077(18) 0.0096(17) C6 0.026(2) 0.021(2) 0.025(2) 0.0053(17) 0.0064(16) 0.0051(16) C7 0.021(2) 0.020(2) 0.0227(19) 0.0063(17) 0.0065(15) 0.0033(15) C8 0.0159(19) 0.0159(18) 0.0226(19) 0.0042(16) 0.0018(14) 0.0010(14) C9 0.0166(19) 0.0179(19) 0.0231(19) 0.0033(16) 0.0025(15) -0.0019(14) C10 0.0132(19) 0.023(2) 0.031(2) 0.0088(18) 0.0034(15) 0.0037(15) C11 0.019(2) 0.027(2) 0.037(2) 0.009(2) 0.0065(17) 0.0014(16) C12 0.028(2) 0.034(2) 0.051(3) 0.023(2) 0.021(2) 0.0098(19) C13 0.028(2) 0.037(3) 0.045(3) 0.020(2) 0.020(2) 0.0115(19) C14 0.028(2) 0.028(2) 0.036(2) 0.012(2) 0.0146(18) 0.0126(18) C15 0.017(2) 0.025(2) 0.030(2) 0.0126(18) 0.0054(16) 0.0082(16) C16 0.0161(19) 0.0217(19) 0.029(2) 0.0116(17) 0.0075(15) 0.0061(15) C17 0.022(2) 0.0160(18) 0.026(2) 0.0071(17) 0.0057(16) 0.0063(15) C18 0.024(2) 0.0189(19) 0.025(2) 0.0060(17) 0.0040(16) 0.0011(15) C19 0.029(2) 0.029(2) 0.027(2) 0.0096(19) 0.0049(17) 0.0061(18) C20 0.037(3) 0.020(2) 0.026(2) 0.0019(18) -0.0010(18) 0.0000(18) C21 0.026(2) 0.024(2) 0.034(2) 0.0074(19) -0.0028(17) -0.0042(17) C22 0.019(2) 0.029(2) 0.038(2) 0.014(2) -0.0004(17) 0.0002(16) C23 0.024(2) 0.021(2) 0.030(2) 0.0101(18) 0.0037(16) 0.0049(16) C24 0.0162(19) 0.0178(19) 0.028(2) 0.0083(17) 0.0019(15) 0.0005(14) C25 0.0179(19) 0.0196(19) 0.0238(19) 0.0062(16) 0.0044(15) 0.0039(15) C26 0.020(2) 0.0144(18) 0.028(2) 0.0065(17) 0.0010(15) -0.0017(14) C27 0.0147(19) 0.024(2) 0.028(2) 0.0073(18) 0.0003(15) 0.0001(15) C28 0.0157(19) 0.023(2) 0.029(2) 0.0085(18) 0.0027(15) 0.0045(15) C29 0.020(2) 0.0193(19) 0.025(2) 0.0078(17) 0.0013(15) 0.0000(15) C30 0.0179(19) 0.0207(19) 0.026(2) 0.0079(17) 0.0060(15) 0.0021(15) B1 0.017(2) 0.017(2) 0.032(2) 0.0087(19) 0.0073(18) 0.0019(16) C1S 0.050(3) 0.038(3) 0.033(3) 0.012(2) -0.003(2) -0.003(2) C2S 0.039(3) 0.046(3) 0.039(3) 0.024(2) 0.000(2) -0.004(2) C3S 0.047(3) 0.043(3) 0.045(3) 0.019(2) 0.015(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C26 1.890(4) . ? Br2 C27 1.887(4) . ? Br3 C28 1.899(4) . ? Br4 C29 1.884(4) . ? Br5 C30 1.897(4) . ? O1 C25 1.365(4) . ? O1 B1 1.468(6) . ? N1 C8 1.365(5) . ? N1 C1 1.370(5) . ? N1 B1 1.492(5) . ? N2 C8 1.343(5) . ? N2 C9 1.347(5) . ? N3 C16 1.372(5) . ? N3 C9 1.379(5) . ? N3 B1 1.483(6) . ? N4 C17 1.340(5) . ? N4 C16 1.355(5) . ? N5 C24 1.349(5) . ? N5 C17 1.367(4) . ? N5 B1 1.501(5) . ? N6 C1 1.345(5) . ? N6 C24 1.352(5) . ? C1 C2 1.456(5) . ? C2 C3 1.394(5) . ? C2 C7 1.420(5) . ? C3 C4 1.392(6) . ? C3 H3A 0.9500 . ? C4 C5 1.392(6) . ? C4 H4A 0.9500 . ? C5 C6 1.384(6) . ? C5 H5A 0.9500 . ? C6 C7 1.405(6) . ? C6 H6A 0.9500 . ? C7 C8 1.460(5) . ? C9 C10 1.445(5) . ? C10 C11 1.374(6) . ? C10 C15 1.438(5) . ? C11 C12 1.380(6) . ? C11 H11A 0.9500 . ? C12 C13 1.397(6) . ? C12 H12A 0.9500 . ? C13 C14 1.370(6) . ? C13 H13A 0.9500 . ? C14 C15 1.397(5) . ? C14 H14A 0.9500 . ? C15 C16 1.444(6) . ? C17 C18 1.451(5) . ? C18 C19 1.401(5) . ? C18 C23 1.425(6) . ? C19 C20 1.376(6) . ? C19 H19A 0.9500 . ? C20 C21 1.404(6) . ? C20 H20A 0.9500 . ? C21 C22 1.372(6) . ? C21 H21A 0.9500 . ? C22 C23 1.388(6) . ? C22 H22A 0.9500 . ? C23 C24 1.455(5) . ? C25 C30 1.388(6) . ? C25 C26 1.397(5) . ? C26 C27 1.401(5) . ? C27 C28 1.384(6) . ? C28 C29 1.397(5) . ? C29 C30 1.400(5) . ? C1S C2S 1.371(7) . ? C1S C3S 1.389(7) 2_665 ? C1S H1S 0.9500 . ? C2S C3S 1.381(7) . ? C2S H2SA 0.9500 . ? C3S C1S 1.389(7) 2_665 ? C3S H3S 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 C25 O1 B1 115.6(3) . . ? C8 N1 C1 113.4(3) . . ? C8 N1 B1 122.9(3) . . ? C1 N1 B1 122.0(3) . . ? C8 N2 C9 117.9(3) . . ? C16 N3 C9 112.6(3) . . ? C16 N3 B1 123.2(3) . . ? C9 N3 B1 123.5(3) . . ? C17 N4 C16 116.7(3) . . ? C24 N5 C17 113.8(3) . . ? C24 N5 B1 122.9(3) . . ? C17 N5 B1 122.8(3) . . ? C1 N6 C24 116.8(3) . . ? N6 C1 N1 123.2(3) . . ? N6 C1 C2 129.5(4) . . ? N1 C1 C2 105.5(3) . . ? C3 C2 C7 121.1(4) . . ? C3 C2 C1 131.5(4) . . ? C7 C2 C1 107.3(3) . . ? C4 C3 C2 117.5(4) . . ? C4 C3 H3A 121.2 . . ? C2 C3 H3A 121.2 . . ? C3 C4 C5 121.3(4) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C6 C5 C4 122.0(4) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C5 C6 C7 117.5(4) . . ? C5 C6 H6A 121.2 . . ? C7 C6 H6A 121.2 . . ? C6 C7 C2 120.3(4) . . ? C6 C7 C8 132.4(4) . . ? C2 C7 C8 107.2(3) . . ? N2 C8 N1 122.5(3) . . ? N2 C8 C7 129.9(4) . . ? N1 C8 C7 105.3(3) . . ? N2 C9 N3 121.2(3) . . ? N2 C9 C10 131.2(4) . . ? N3 C9 C10 106.2(3) . . ? C11 C10 C15 119.7(4) . . ? C11 C10 C9 133.7(4) . . ? C15 C10 C9 106.4(3) . . ? C10 C11 C12 118.9(4) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? C11 C12 C13 121.7(4) . . ? C11 C12 H12A 119.1 . . ? C13 C12 H12A 119.1 . . ? C14 C13 C12 120.7(4) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 118.7(4) . . ? C13 C14 H14A 120.6 . . ? C15 C14 H14A 120.6 . . ? C14 C15 C10 120.2(4) . . ? C14 C15 C16 131.9(4) . . ? C10 C15 C16 107.8(3) . . ? N4 C16 N3 122.0(3) . . ? N4 C16 C15 130.7(3) . . ? N3 C16 C15 105.6(3) . . ? N4 C17 N5 122.7(3) . . ? N4 C17 C18 130.6(3) . . ? N5 C17 C18 105.1(3) . . ? C19 C18 C23 120.5(4) . . ? C19 C18 C17 131.8(4) . . ? C23 C18 C17 107.7(3) . . ? C20 C19 C18 117.5(4) . . ? C20 C19 H19A 121.2 . . ? C18 C19 H19A 121.2 . . ? C19 C20 C21 121.7(4) . . ? C19 C20 H20A 119.1 . . ? C21 C20 H20A 119.1 . . ? C22 C21 C20 121.5(4) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C21 C22 C23 118.1(4) . . ? C21 C22 H22A 121.0 . . ? C23 C22 H22A 121.0 . . ? C22 C23 C18 120.7(4) . . ? C22 C23 C24 132.8(4) . . ? C18 C23 C24 106.4(3) . . ? N5 C24 N6 122.4(3) . . ? N5 C24 C23 106.2(3) . . ? N6 C24 C23 129.8(3) . . ? O1 C25 C30 121.6(3) . . ? O1 C25 C26 120.0(3) . . ? C30 C25 C26 118.4(3) . . ? C25 C26 C27 120.7(4) . . ? C25 C26 Br1 118.3(3) . . ? C27 C26 Br1 121.1(3) . . ? C28 C27 C26 119.4(4) . . ? C28 C27 Br2 121.4(3) . . ? C26 C27 Br2 119.1(3) . . ? C27 C28 C29 120.8(3) . . ? C27 C28 Br3 119.7(3) . . ? C29 C28 Br3 119.5(3) . . ? C28 C29 C30 118.6(4) . . ? C28 C29 Br4 121.0(3) . . ? C30 C29 Br4 120.3(3) . . ? C25 C30 C29 121.6(4) . . ? C25 C30 Br5 118.0(3) . . ? C29 C30 Br5 120.5(3) . . ? O1 B1 N3 116.7(3) . . ? O1 B1 N1 111.6(3) . . ? N3 B1 N1 104.5(3) . . ? O1 B1 N5 114.9(4) . . ? N3 B1 N5 103.1(3) . . ? N1 B1 N5 104.7(3) . . ? C2S C1S C3S 119.9(4) . 2_665 ? C2S C1S H1S 120.0 . . ? C3S C1S H1S 120.0 2_665 . ? C1S C2S C3S 121.0(5) . . ? C1S C2S H2SA 119.5 . . ? C3S C2S H2SA 119.5 . . ? C2S C3S C1S 119.0(5) . 2_665 ? C2S C3S H3S 120.5 . . ? C1S C3S H3S 120.5 2_665 . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.956 _refine_diff_density_min -1.067 _refine_diff_density_rms 0.149 data_k1190twin _database_code_depnum_ccdc_archive 'CCDC 906285' #TrackingRef '4f Br5PhO-BsubPc k1190twin.cif' # start Validation Reply Form _vrf_PLAT934_k1190twin ; RESPONSE: The CIF includes two reflections for which I(obs) and I(calc) differ by more than 10 times SigmaW (3 -6 3 and 0 9 2). These outliers do not appear to be the result of systematic errors, i.e., they are not the result of the geometry of the diffractometer, and therefore we have left these reflections in the data. This crystal was a twin, and although the best possible twin law was applied, there may still be slight discrepancies between the observed data and the model, which may then result in outlier reflections. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Pentabromophenolato)(subphthalocyaninato)boron ; _chemical_name_common (Pentabromophenolato)(subphthalocyaninato)boron _chemical_melting_point ? _chemical_formula_moiety 'C30 H12 B Br5 N6 O' _chemical_formula_sum 'C30 H12 B Br5 N6 O' _chemical_formula_weight 882.82 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' B B 0.0013 0.0007 '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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4976(3) _cell_length_b 12.9454(4) _cell_length_c 13.9650(5) _cell_angle_alpha 107.2430(18) _cell_angle_beta 97.553(2) _cell_angle_gamma 101.703(2) _cell_volume 1406.21(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 4953 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.085 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 7.184 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_T_max 0.871 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 4953 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0804 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4953 _reflns_number_gt 3554 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0866P)^2^+12.0939P] 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 4953 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1717 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.50069(13) 0.48305(9) 0.77953(8) 0.0285(3) Uani 1 1 d . . . Br2 Br 0.47203(14) 0.64294(9) 0.63445(9) 0.0338(3) Uani 1 1 d . . . Br3 Br 0.20597(15) 0.54248(10) 0.41408(9) 0.0348(3) Uani 1 1 d . . . Br4 Br -0.02294(16) 0.28481(11) 0.34004(9) 0.0445(4) Uani 1 1 d . . . Br5 Br 0.01190(14) 0.13013(9) 0.48751(8) 0.0329(3) Uani 1 1 d . . . O1 O 0.2535(8) 0.2603(5) 0.6883(5) 0.0231(16) Uani 1 1 d . . . N1 N 0.2189(10) 0.2136(7) 0.8438(6) 0.0224(19) Uani 1 1 d . . . N2 N 0.3355(10) 0.3902(7) 0.9746(6) 0.025(2) Uani 1 1 d . . . N3 N 0.1424(10) 0.3747(7) 0.8299(6) 0.0217(19) Uani 1 1 d . . . N4 N -0.1262(10) 0.3556(7) 0.7407(6) 0.0212(19) Uani 1 1 d . . . N5 N -0.0213(10) 0.1950(7) 0.7273(6) 0.0205(18) Uani 1 1 d . . . N6 N 0.0175(10) 0.0401(7) 0.7757(7) 0.025(2) Uani 1 1 d . . . C1 C 0.1587(13) 0.1056(8) 0.8384(8) 0.026(2) Uani 1 1 d . . . C2 C 0.2514(13) 0.0952(9) 0.9286(9) 0.029(3) Uani 1 1 d . . . C3 C 0.2431(16) 0.0033(10) 0.9634(9) 0.038(3) Uani 1 1 d . . . H3A H 0.1733 -0.0681 0.9234 0.045 Uiso 1 1 calc R . . C4 C 0.3383(18) 0.0191(11) 1.0564(10) 0.046(3) Uani 1 1 d . . . H4A H 0.3353 -0.0417 1.0817 0.055 Uiso 1 1 calc R . . C5 C 0.4402(17) 0.1256(11) 1.1141(10) 0.045(3) Uani 1 1 d . . . H5A H 0.5076 0.1346 1.1774 0.054 Uiso 1 1 calc R . . C6 C 0.4469(14) 0.2169(9) 1.0832(9) 0.031(3) Uani 1 1 d . . . H6A H 0.5158 0.2881 1.1245 0.037 Uiso 1 1 calc R . . C7 C 0.3498(13) 0.2026(9) 0.9894(9) 0.028(2) Uani 1 1 d . . . C8 C 0.3164(12) 0.2798(9) 0.9378(8) 0.026(2) Uani 1 1 d . . . C9 C 0.2403(12) 0.4357(8) 0.9229(7) 0.018(2) Uani 1 1 d . . . C10 C 0.1915(13) 0.5399(8) 0.9525(8) 0.023(2) Uani 1 1 d . . . C11 C 0.2543(14) 0.6383(9) 1.0399(8) 0.028(2) Uani 1 1 d . . . H11A H 0.3452 0.6445 1.0906 0.034 Uiso 1 1 calc R . . C12 C 0.1779(14) 0.7247(9) 1.0481(8) 0.029(3) Uani 1 1 d . . . H12A H 0.2194 0.7920 1.1047 0.035 Uiso 1 1 calc R . . C13 C 0.0418(13) 0.7152(9) 0.9755(9) 0.030(3) Uani 1 1 d . . . H13A H -0.0086 0.7756 0.9838 0.036 Uiso 1 1 calc R . . C14 C -0.0217(13) 0.6179(8) 0.8907(8) 0.025(2) Uani 1 1 d . . . H14A H -0.1148 0.6116 0.8415 0.030 Uiso 1 1 calc R . . C15 C 0.0542(13) 0.5302(8) 0.8795(8) 0.025(2) Uani 1 1 d . . . C16 C 0.0132(13) 0.4190(8) 0.8055(8) 0.023(2) Uani 1 1 d . . . C17 C -0.1436(12) 0.2451(8) 0.7090(8) 0.024(2) Uani 1 1 d . . . C18 C -0.2964(13) 0.1525(8) 0.6724(8) 0.023(2) Uani 1 1 d . . . C19 C -0.4580(13) 0.1496(10) 0.6430(9) 0.033(3) Uani 1 1 d . . . H19A H -0.4892 0.2149 0.6389 0.039 Uiso 1 1 calc R . . C20 C -0.5739(15) 0.0500(10) 0.6193(10) 0.040(3) Uani 1 1 d . . . H20A H -0.6860 0.0460 0.5964 0.048 Uiso 1 1 calc R . . C21 C -0.5297(13) -0.0467(10) 0.6285(9) 0.037(3) Uani 1 1 d . . . H21A H -0.6133 -0.1137 0.6130 0.044 Uiso 1 1 calc R . . C22 C -0.3680(13) -0.0463(9) 0.6593(8) 0.031(3) Uani 1 1 d . . . H22A H -0.3383 -0.1113 0.6657 0.037 Uiso 1 1 calc R . . C23 C -0.2494(13) 0.0558(9) 0.6809(8) 0.029(3) Uani 1 1 d . . . C24 C -0.0728(13) 0.0878(8) 0.7260(7) 0.022(2) Uani 1 1 d . . . C25 C 0.2417(13) 0.3240(8) 0.6267(7) 0.022(2) Uani 1 1 d . . . C26 C 0.3452(13) 0.4319(8) 0.6565(8) 0.022(2) Uani 1 1 d . . . C27 C 0.3328(13) 0.4960(9) 0.5939(8) 0.029(3) Uani 1 1 d . . . C28 C 0.2228(13) 0.4553(9) 0.4995(8) 0.025(2) Uani 1 1 d . . . C29 C 0.1242(13) 0.3458(10) 0.4680(8) 0.030(3) Uani 1 1 d . . . C30 C 0.1357(13) 0.2814(9) 0.5325(8) 0.026(2) Uani 1 1 d . . . B1 B 0.1537(14) 0.2617(9) 0.7679(8) 0.018(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 Br1 0.0263(6) 0.0315(6) 0.0251(6) 0.0106(5) 0.0030(4) 0.0015(5) Br2 0.0401(7) 0.0267(6) 0.0338(7) 0.0128(5) 0.0081(5) 0.0027(5) Br3 0.0459(7) 0.0365(7) 0.0293(6) 0.0179(5) 0.0100(5) 0.0145(5) Br4 0.0525(8) 0.0480(8) 0.0247(6) 0.0127(5) -0.0040(6) 0.0013(6) Br5 0.0408(7) 0.0257(6) 0.0243(6) 0.0029(5) 0.0050(5) 0.0005(5) O1 0.024(4) 0.019(4) 0.025(4) 0.003(3) 0.012(3) 0.006(3) N1 0.031(5) 0.019(4) 0.022(5) 0.009(4) 0.010(4) 0.011(4) N2 0.018(4) 0.028(5) 0.023(5) 0.006(4) 0.002(4) 0.001(4) N3 0.022(4) 0.024(5) 0.018(4) 0.008(4) 0.004(4) 0.004(4) N4 0.023(5) 0.024(5) 0.019(4) 0.005(4) 0.008(4) 0.012(4) N5 0.024(5) 0.020(4) 0.020(4) 0.007(3) 0.007(4) 0.009(4) N6 0.025(5) 0.021(4) 0.025(5) 0.005(4) 0.006(4) 0.004(4) C1 0.030(6) 0.019(5) 0.030(6) 0.007(5) 0.013(5) 0.007(5) C2 0.029(6) 0.027(6) 0.039(7) 0.015(5) 0.014(5) 0.013(5) C3 0.058(8) 0.027(6) 0.037(7) 0.017(5) 0.007(6) 0.023(6) C4 0.072(10) 0.035(7) 0.033(7) 0.016(6) 0.013(7) 0.015(7) C5 0.061(9) 0.045(8) 0.029(7) 0.014(6) 0.001(6) 0.015(7) C6 0.037(7) 0.027(6) 0.031(6) 0.010(5) 0.006(5) 0.009(5) C7 0.034(6) 0.024(6) 0.035(6) 0.017(5) 0.011(5) 0.011(5) C8 0.021(5) 0.029(6) 0.028(6) 0.006(5) 0.011(5) 0.006(5) C9 0.023(5) 0.014(5) 0.019(5) 0.008(4) 0.010(4) 0.003(4) C10 0.033(6) 0.017(5) 0.024(6) 0.008(4) 0.016(5) 0.007(4) C11 0.036(6) 0.028(6) 0.019(5) 0.008(5) 0.009(5) 0.003(5) C12 0.034(6) 0.025(6) 0.025(6) 0.002(5) 0.011(5) 0.008(5) C13 0.031(6) 0.027(6) 0.039(7) 0.014(5) 0.016(5) 0.013(5) C14 0.034(6) 0.022(5) 0.021(5) 0.007(4) 0.011(5) 0.005(5) C15 0.026(6) 0.016(5) 0.033(6) 0.013(5) 0.009(5) -0.003(4) C16 0.029(6) 0.023(5) 0.024(6) 0.011(5) 0.014(5) 0.010(5) C17 0.024(6) 0.020(5) 0.026(6) 0.007(4) 0.004(4) -0.002(4) C18 0.026(6) 0.018(5) 0.021(5) 0.002(4) 0.002(4) 0.003(4) C19 0.029(6) 0.033(6) 0.034(7) 0.007(5) 0.003(5) 0.012(5) C20 0.030(6) 0.031(6) 0.053(8) 0.020(6) -0.004(6) -0.003(5) C21 0.019(6) 0.038(7) 0.043(7) 0.007(6) 0.001(5) -0.002(5) C22 0.030(6) 0.023(6) 0.030(6) -0.002(5) 0.005(5) 0.000(5) C23 0.030(6) 0.033(6) 0.023(6) 0.010(5) 0.003(5) 0.006(5) C24 0.030(6) 0.019(5) 0.016(5) 0.005(4) 0.008(4) 0.005(4) C25 0.032(6) 0.023(5) 0.016(5) 0.008(4) 0.008(4) 0.012(5) C26 0.027(5) 0.024(5) 0.023(5) 0.013(4) 0.011(4) 0.012(4) C27 0.024(6) 0.036(6) 0.025(6) 0.011(5) 0.006(5) 0.004(5) C28 0.032(6) 0.031(6) 0.022(6) 0.017(5) 0.011(5) 0.013(5) C29 0.029(6) 0.039(7) 0.020(6) 0.010(5) 0.005(5) 0.007(5) C30 0.035(6) 0.023(5) 0.023(6) 0.007(4) 0.008(5) 0.012(5) B1 0.021(6) 0.019(6) 0.015(6) 0.006(5) 0.008(5) 0.001(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 Br1 C26 1.873(10) . ? Br2 C27 1.900(11) . ? Br3 C28 1.880(10) . ? Br4 C29 1.886(11) . ? Br5 C30 1.897(11) . ? O1 C25 1.364(12) . ? O1 B1 1.483(13) . ? N1 C1 1.363(13) . ? N1 C8 1.380(13) . ? N1 B1 1.481(14) . ? N2 C8 1.334(14) . ? N2 C9 1.347(13) . ? N3 C9 1.359(12) . ? N3 C16 1.387(13) . ? N3 B1 1.492(14) . ? N4 C16 1.334(13) . ? N4 C17 1.337(13) . ? N5 C24 1.361(13) . ? N5 C17 1.366(13) . ? N5 B1 1.499(14) . ? N6 C24 1.325(13) . ? N6 C1 1.340(13) . ? C1 C2 1.452(16) . ? C2 C3 1.404(15) . ? C2 C7 1.412(15) . ? C3 C4 1.372(17) . ? C3 H3A 0.9500 . ? C4 C5 1.405(18) . ? C4 H4A 0.9500 . ? C5 C6 1.366(17) . ? C5 H5A 0.9500 . ? C6 C7 1.394(16) . ? C6 H6A 0.9500 . ? C7 C8 1.445(15) . ? C9 C10 1.450(14) . ? C10 C15 1.403(15) . ? C10 C11 1.424(14) . ? C11 C12 1.387(16) . ? C11 H11A 0.9500 . ? C12 C13 1.393(16) . ? C12 H12A 0.9500 . ? C13 C14 1.397(15) . ? C13 H13A 0.9500 . ? C14 C15 1.396(15) . ? C14 H14A 0.9500 . ? C15 C16 1.442(14) . ? C17 C18 1.488(14) . ? C18 C19 1.371(15) . ? C18 C23 1.421(15) . ? C19 C20 1.375(16) . ? C19 H19A 0.9500 . ? C20 C21 1.413(17) . ? C20 H20A 0.9500 . ? C21 C22 1.384(16) . ? C21 H21A 0.9500 . ? C22 C23 1.413(15) . ? C22 H22A 0.9500 . ? C23 C24 1.472(15) . ? C25 C30 1.379(14) . ? C25 C26 1.400(14) . ? C26 C27 1.380(15) . ? C27 C28 1.398(15) . ? C28 C29 1.399(15) . ? C29 C30 1.404(16) . ? 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 C25 O1 B1 121.7(8) . . ? C1 N1 C8 113.1(9) . . ? C1 N1 B1 123.1(9) . . ? C8 N1 B1 122.1(8) . . ? C8 N2 C9 117.9(9) . . ? C9 N3 C16 113.1(8) . . ? C9 N3 B1 123.7(8) . . ? C16 N3 B1 122.4(8) . . ? C16 N4 C17 116.8(9) . . ? C24 N5 C17 115.3(8) . . ? C24 N5 B1 122.2(9) . . ? C17 N5 B1 121.2(8) . . ? C24 N6 C1 117.2(9) . . ? N6 C1 N1 122.5(10) . . ? N6 C1 C2 130.4(10) . . ? N1 C1 C2 105.0(9) . . ? C3 C2 C7 121.1(11) . . ? C3 C2 C1 130.7(10) . . ? C7 C2 C1 107.9(9) . . ? C4 C3 C2 118.5(11) . . ? C4 C3 H3A 120.8 . . ? C2 C3 H3A 120.8 . . ? C3 C4 C5 119.6(12) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C6 C5 C4 123.0(12) . . ? C6 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? C5 C6 C7 118.2(11) . . ? C5 C6 H6A 120.9 . . ? C7 C6 H6A 120.9 . . ? C6 C7 C2 119.6(10) . . ? C6 C7 C8 132.9(10) . . ? C2 C7 C8 107.4(9) . . ? N2 C8 N1 122.8(10) . . ? N2 C8 C7 130.4(10) . . ? N1 C8 C7 105.1(9) . . ? N2 C9 N3 121.5(9) . . ? N2 C9 C10 132.7(9) . . ? N3 C9 C10 104.8(8) . . ? C15 C10 C11 120.8(10) . . ? C15 C10 C9 108.2(9) . . ? C11 C10 C9 131.0(10) . . ? C12 C11 C10 117.5(10) . . ? C12 C11 H11A 121.2 . . ? C10 C11 H11A 121.2 . . ? C11 C12 C13 121.7(10) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C12 C13 C14 120.8(10) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C15 C14 C13 118.8(10) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C14 C15 C10 120.4(9) . . ? C14 C15 C16 132.0(10) . . ? C10 C15 C16 107.6(9) . . ? N4 C16 N3 122.0(9) . . ? N4 C16 C15 131.9(10) . . ? N3 C16 C15 104.7(9) . . ? N4 C17 N5 124.4(9) . . ? N4 C17 C18 129.3(10) . . ? N5 C17 C18 104.6(8) . . ? C19 C18 C23 121.0(10) . . ? C19 C18 C17 132.6(10) . . ? C23 C18 C17 106.2(9) . . ? C18 C19 C20 118.4(11) . . ? C18 C19 H19A 120.8 . . ? C20 C19 H19A 120.8 . . ? C19 C20 C21 121.3(11) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.8(11) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C23 116.4(11) . . ? C21 C22 H22A 121.8 . . ? C23 C22 H22A 121.8 . . ? C22 C23 C18 121.0(10) . . ? C22 C23 C24 130.0(10) . . ? C18 C23 C24 108.5(9) . . ? N6 C24 N5 123.4(9) . . ? N6 C24 C23 131.2(9) . . ? N5 C24 C23 103.9(9) . . ? O1 C25 C30 120.9(9) . . ? O1 C25 C26 119.7(9) . . ? C30 C25 C26 119.2(9) . . ? C27 C26 C25 119.5(9) . . ? C27 C26 Br1 122.1(8) . . ? C25 C26 Br1 118.4(7) . . ? C26 C27 C28 122.0(10) . . ? C26 C27 Br2 119.7(8) . . ? C28 C27 Br2 118.3(8) . . ? C27 C28 C29 118.4(10) . . ? C27 C28 Br3 122.0(8) . . ? C29 C28 Br3 119.6(8) . . ? C28 C29 C30 119.4(10) . . ? C28 C29 Br4 120.4(8) . . ? C30 C29 Br4 120.1(8) . . ? C25 C30 C29 121.4(10) . . ? C25 C30 Br5 118.7(8) . . ? C29 C30 Br5 119.8(8) . . ? N1 B1 O1 112.1(9) . . ? N1 B1 N3 105.1(8) . . ? O1 B1 N3 115.3(8) . . ? N1 B1 N5 104.7(8) . . ? O1 B1 N5 114.3(8) . . ? N3 B1 N5 104.4(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.015 _refine_diff_density_min -1.043 _refine_diff_density_rms 0.215