#------------------------------------------------------------------------------ #$Date: 2014-10-25 18:23:10 +0100 (Sat, 25 Oct 2014) $ #$Revision: 125873 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/53/2105302.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2105302 loop_ _publ_author_name 'Fulford, Mabel V.' 'Lough, Alan John' 'Bender, Timothy P.' _publ_section_title ; The first report of the crystal structure of non-solvated \m-oxo boron subphthalocyanine and the crystal structures of two solvated forms ; _journal_coeditor_code RY5043 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 636 _journal_page_last 645 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C48 H24 B2 N12 O' _chemical_formula_sum 'C48 H24 B2 N12 O' _chemical_formula_weight 806.41 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 124.401(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 25.6932(18) _cell_length_b 8.3375(5) _cell_length_c 20.8860(16) _cell_measurement_reflns_used 12572 _cell_measurement_temperature 147.0(10) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 2.6 _cell_volume 3691.6(5) _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_data_reduction Denzo-SMN _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _diffrn_ambient_temperature 147.0(10) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1384 _diffrn_reflns_av_sigmaI/netI 0.1052 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12572 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.63 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1.007 _exptl_absorpt_correction_T_min 0.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1656 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.473 _refine_diff_density_min -0.296 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 285 _refine_ls_number_reflns 3233 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.1491 _refine_ls_R_factor_gt 0.0881 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0855P)^2^+8.4419P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1972 _refine_ls_wR_factor_ref 0.2286 _reflns_number_gt 1908 _reflns_number_total 3233 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL k11292 in C2/c CELL 0.71073 25.6932 8.3375 20.8860 90.000 124.401 90.000 ZERR 4 0.0018 0.0005 0.0016 0.0000 0.0026 0.0000 LATT 7 SYMM - X, + Y, 1/2 - Z SFAC C H B N O DISP C 0.00330 0.00160 DISP H 0.00000 0.00000 DISP B 0.00130 0.00070 DISP N 0.00610 0.00330 DISP O 0.01060 0.00600 UNIT 192 96 8 48 4 TEMP -126 SIZE 0.2, 0.1, 0.1 ACTA 50 BOND $H FMAP 2 PLAN 20 L.S. 4 WGHT 0.0855 8.4419 FVAR 0.15561 O1 5 0.500000 0.331791 0.250000 10.50000 0.04333 0.03970 = 0.04359 0.00000 0.01934 0.00000 N1 4 0.410667 0.515309 0.213061 11.00000 0.04419 0.03775 = 0.04298 0.00194 0.02548 -0.00029 N2 4 0.435189 0.753052 0.173208 11.00000 0.04092 0.03955 = 0.04486 0.00173 0.02290 0.00198 N3 4 0.444155 0.499496 0.128954 11.00000 0.03866 0.03775 = 0.04712 -0.00084 0.02260 0.00043 N4 4 0.401665 0.291922 0.034019 11.00000 0.03846 0.04610 = 0.04792 -0.00117 0.02259 0.00284 N5 4 0.392288 0.279486 0.141157 11.00000 0.04023 0.04209 = 0.03932 0.00329 0.02092 0.00399 N6 4 0.336727 0.323449 0.200198 11.00000 0.03724 0.04247 = 0.04662 0.00333 0.02310 0.00129 C1 1 0.367398 0.465672 0.226511 11.00000 0.04341 0.04841 = 0.03298 0.00392 0.01855 0.00265 C2 1 0.350440 0.607841 0.252424 11.00000 0.03989 0.04876 = 0.03794 -0.00177 0.01840 0.00072 C3 1 0.310455 0.631346 0.276139 11.00000 0.04221 0.05787 = 0.04044 0.00040 0.02053 -0.00364 AFIX 43 H3A 2 0.288391 0.544192 0.279697 11.00000 -1.20000 AFIX 0 C4 1 0.303622 0.786469 0.294570 11.00000 0.05231 0.05552 = 0.04840 0.00177 0.03067 0.01272 AFIX 43 H4A 2 0.276976 0.805511 0.311821 11.00000 -1.20000 AFIX 0 C5 1 0.335120 0.914272 0.288194 11.00000 0.04883 0.04731 = 0.05325 -0.00301 0.02308 0.00740 AFIX 43 H5A 2 0.330078 1.018649 0.302199 11.00000 -1.20000 AFIX 0 C6 1 0.373046 0.894419 0.262445 11.00000 0.04404 0.04511 = 0.04027 -0.00252 0.01617 0.00386 AFIX 43 H6A 2 0.393249 0.983593 0.256962 11.00000 -1.20000 AFIX 0 C7 1 0.381391 0.739489 0.244353 11.00000 0.03611 0.04936 = 0.03099 0.00069 0.01260 0.00336 C8 1 0.415519 0.678469 0.212746 11.00000 0.03480 0.04093 = 0.03555 0.00094 0.01164 0.00207 C9 1 0.445745 0.662434 0.128902 11.00000 0.02791 0.04032 = 0.04466 0.00095 0.01307 0.00022 C10 1 0.444681 0.708601 0.060991 11.00000 0.03780 0.04603 = 0.05243 0.00373 0.02552 -0.00154 C11 1 0.445957 0.856645 0.031785 11.00000 0.04089 0.05421 = 0.05148 0.00354 0.02425 -0.00107 AFIX 43 H11A 2 0.451606 0.952780 0.059445 11.00000 -1.20000 AFIX 0 C12 1 0.438671 0.859623 -0.039539 11.00000 0.05231 0.06043 = 0.06259 0.01043 0.03515 -0.00070 AFIX 43 H12A 2 0.439971 0.959652 -0.060377 11.00000 -1.20000 AFIX 0 C13 1 0.429533 0.719723 -0.081064 11.00000 0.05362 0.07295 = 0.05210 0.00586 0.03306 -0.00982 AFIX 43 H13A 2 0.425272 0.725837 -0.129239 11.00000 -1.20000 AFIX 0 C14 1 0.426584 0.572739 -0.053336 11.00000 0.03848 0.06303 = 0.04015 -0.00145 0.01831 -0.00471 AFIX 43 H14A 2 0.419007 0.477832 -0.082569 11.00000 -1.20000 AFIX 0 C15 1 0.434919 0.566294 0.018210 11.00000 0.03861 0.05509 = 0.04380 -0.00052 0.02293 -0.00355 C16 1 0.430074 0.435653 0.060842 11.00000 0.03654 0.04334 = 0.05322 -0.00243 0.02722 0.00195 C17 1 0.378896 0.223221 0.072155 11.00000 0.03972 0.04302 = 0.04770 -0.00040 0.02581 0.00565 C18 1 0.325818 0.111989 0.042564 11.00000 0.03230 0.03900 = 0.04105 -0.00052 0.01416 0.00211 C19 1 0.293454 0.020648 -0.024786 11.00000 0.04233 0.03969 = 0.04695 0.00511 0.02346 0.00574 AFIX 43 H19A 2 0.306093 0.016492 -0.059609 11.00000 -1.20000 AFIX 0 C20 1 0.241741 -0.064053 -0.038404 11.00000 0.04417 0.03878 = 0.04809 -0.00299 0.01888 0.00000 AFIX 43 H20A 2 0.219470 -0.131881 -0.082601 11.00000 -1.20000 AFIX 0 C21 1 0.221425 -0.052930 0.010536 11.00000 0.03765 0.03838 = 0.05163 0.00152 0.01853 -0.00032 AFIX 43 H21A 2 0.185295 -0.111795 -0.001465 11.00000 -1.20000 AFIX 0 C22 1 0.252644 0.042011 0.076406 11.00000 0.03776 0.04322 = 0.05163 0.00274 0.02382 0.00502 AFIX 43 H22A 2 0.238241 0.050433 0.109335 11.00000 -1.20000 AFIX 0 C23 1 0.306028 0.124910 0.092721 11.00000 0.03139 0.04677 = 0.04236 -0.00141 0.01700 -0.00226 C24 1 0.346590 0.240277 0.153116 11.00000 0.03787 0.04239 = 0.04446 0.00485 0.02341 0.00543 B1 3 0.442881 0.402887 0.189268 11.00000 0.03556 0.03987 = 0.04838 -0.00304 0.02136 -0.00531 HKLF 4 REM k11292 in C2/c REM R1 = 0.0882 for 1908 Fo > 4sig(Fo) and 0.1492 for all 3233 data REM 285 parameters refined using 0 restraints END REM Highest difference peak 0.471, deepest hole -0.297, 1-sigma level 0.078 Q1 1 0.4982 1.0573 0.1850 11.00000 0.05 0.47 Q2 1 0.3545 0.2890 0.0917 11.00000 0.05 0.32 Q3 1 0.4257 0.5905 0.0460 11.00000 0.05 0.29 Q4 1 0.3789 0.3336 0.0922 11.00000 0.05 0.28 Q5 1 0.3325 0.5766 0.2677 11.00000 0.05 0.26 Q6 1 0.4116 0.8099 0.2152 11.00000 0.05 0.26 Q7 1 0.3885 0.5587 -0.0455 11.00000 0.05 0.26 Q8 1 0.4715 0.8825 0.0032 11.00000 0.05 0.25 Q9 1 0.4031 0.7767 0.0390 11.00000 0.05 0.25 Q10 1 0.3798 0.2126 0.2431 11.00000 0.05 0.25 Q11 1 0.3903 0.7415 0.1468 11.00000 0.05 0.25 Q12 1 0.4777 0.4281 0.0405 11.00000 0.05 0.25 Q13 1 0.3446 0.8092 0.2786 11.00000 0.05 0.25 Q14 1 0.2268 0.0704 0.0029 11.00000 0.05 0.23 Q15 1 0.3455 0.2188 0.2306 11.00000 0.05 0.23 Q16 1 0.4153 0.5054 0.1632 11.00000 0.05 0.23 Q17 1 0.3909 0.2562 0.1996 11.00000 0.05 0.23 Q18 1 0.4348 0.2992 0.0218 11.00000 0.05 0.22 Q19 1 0.3557 0.6807 0.2211 11.00000 0.05 0.22 Q20 1 0.3145 0.2871 0.2304 11.00000 0.05 0.22 ; _[local]_cod_data_source_file ry5043.cif _[local]_cod_data_source_block m-oxo-BsubPc-subl _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 3691.6(4) _cod_database_code 2105302 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity O O1 0.5000 0.3318(5) 0.2500 0.0452(12) Uani d S 1 2 N N2 0.41066(18) 0.5153(4) 0.2130(2) 0.0412(10) Uani d . 1 1 N N3 0.43519(17) 0.7531(4) 0.1732(2) 0.0426(10) Uani d . 1 1 N N4 0.44415(17) 0.4995(4) 0.1290(2) 0.0422(10) Uani d . 1 1 N N5 0.40166(18) 0.2919(5) 0.0340(2) 0.0453(10) Uani d . 1 1 N N6 0.39229(17) 0.2795(4) 0.1412(2) 0.0415(10) Uani d . 1 1 N N1 0.33673(17) 0.3235(4) 0.2002(2) 0.0426(10) Uani d . 1 1 C C1 0.3674(2) 0.4657(6) 0.2265(3) 0.0433(12) Uani d . 1 1 C C2 0.3504(2) 0.6078(6) 0.2524(3) 0.0443(12) Uani d . 1 1 C C3 0.3105(2) 0.6313(6) 0.2762(3) 0.0485(13) Uani d . 1 1 H H3A 0.2884 0.5442 0.2797 0.058 Uiso calc R 1 1 C C4 0.3036(2) 0.7865(6) 0.2946(3) 0.0509(13) Uani d . 1 1 H H4A 0.2770 0.8055 0.3118 0.061 Uiso calc R 1 1 C C5 0.3351(2) 0.9143(6) 0.2882(3) 0.0531(14) Uani d . 1 1 H H5A 0.3301 1.0186 0.3022 0.064 Uiso calc R 1 1 C C6 0.3730(2) 0.8944(6) 0.2624(3) 0.0474(13) Uani d . 1 1 H H6A 0.3932 0.9836 0.2569 0.057 Uiso calc R 1 1 C C7 0.3814(2) 0.7395(5) 0.2443(3) 0.0424(12) Uani d . 1 1 C C8 0.4155(2) 0.6785(5) 0.2127(3) 0.0417(12) Uani d . 1 1 C C9 0.4457(2) 0.6625(5) 0.1289(3) 0.0419(12) Uani d . 1 1 C C10 0.4447(2) 0.7086(6) 0.0610(3) 0.0455(12) Uani d . 1 1 C C11 0.4460(2) 0.8566(6) 0.0318(3) 0.0500(13) Uani d . 1 1 H H11A 0.4516 0.9528 0.0594 0.060 Uiso calc R 1 1 C C12 0.4387(2) 0.8596(7) -0.0395(3) 0.0571(14) Uani d . 1 1 H H12A 0.4400 0.9597 -0.0603 0.069 Uiso calc R 1 1 C C13 0.4295(2) 0.7197(7) -0.0811(3) 0.0579(15) Uani d . 1 1 H H13A 0.4253 0.7259 -0.1293 0.069 Uiso calc R 1 1 C C14 0.4266(2) 0.5727(6) -0.0533(3) 0.0495(13) Uani d . 1 1 H H14A 0.4190 0.4778 -0.0826 0.059 Uiso calc R 1 1 C C15 0.4349(2) 0.5663(6) 0.0182(3) 0.0461(12) Uani d . 1 1 C C16 0.4301(2) 0.4356(6) 0.0608(3) 0.0434(12) Uani d . 1 1 C C17 0.3789(2) 0.2233(5) 0.0722(3) 0.0429(12) Uani d . 1 1 C C18 0.3258(2) 0.1120(5) 0.0426(3) 0.0412(12) Uani d . 1 1 C C19 0.2935(2) 0.0207(5) -0.0248(3) 0.0440(12) Uani d . 1 1 H H19A 0.3061 0.0165 -0.0596 0.053 Uiso calc R 1 1 C C20 0.2417(2) -0.0640(5) -0.0384(3) 0.0478(13) Uani d . 1 1 H H20A 0.2195 -0.1319 -0.0826 0.057 Uiso calc R 1 1 C C21 0.2214(2) -0.0529(5) 0.0105(3) 0.0464(12) Uani d . 1 1 H H21A 0.1853 -0.1118 -0.0015 0.056 Uiso calc R 1 1 C C22 0.2526(2) 0.0420(5) 0.0764(3) 0.0451(12) Uani d . 1 1 H H22A 0.2382 0.0504 0.1094 0.054 Uiso calc R 1 1 C C23 0.3060(2) 0.1249(6) 0.0927(3) 0.0424(12) Uani d . 1 1 C C24 0.3466(2) 0.2403(5) 0.1531(3) 0.0416(12) Uani d . 1 1 B B1 0.4429(2) 0.4029(6) 0.1893(3) 0.0427(14) Uani d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.043(3) 0.040(2) 0.044(3) 0.000 0.019(2) 0.000 N2 0.044(2) 0.038(2) 0.043(2) -0.0003(17) 0.025(2) 0.0019(18) N3 0.041(2) 0.040(2) 0.045(2) 0.0019(17) 0.023(2) 0.0017(19) N4 0.039(2) 0.038(2) 0.047(3) 0.0004(17) 0.023(2) -0.0008(19) N5 0.039(2) 0.046(2) 0.048(3) 0.0029(18) 0.023(2) -0.0012(19) N6 0.040(2) 0.042(2) 0.039(2) 0.0041(17) 0.021(2) 0.0033(18) N1 0.037(2) 0.043(2) 0.047(2) 0.0013(17) 0.023(2) 0.0033(19) C1 0.043(3) 0.048(3) 0.033(3) 0.002(2) 0.019(2) 0.004(2) C2 0.040(3) 0.049(3) 0.038(3) 0.001(2) 0.018(2) -0.002(2) C3 0.042(3) 0.058(3) 0.041(3) -0.004(2) 0.021(3) 0.000(2) C4 0.052(3) 0.056(3) 0.048(3) 0.013(3) 0.031(3) 0.002(3) C5 0.049(3) 0.047(3) 0.053(3) 0.007(2) 0.023(3) -0.003(3) C6 0.044(3) 0.045(3) 0.040(3) 0.004(2) 0.016(3) -0.002(2) C7 0.036(3) 0.050(3) 0.031(3) 0.003(2) 0.013(2) 0.001(2) C8 0.035(3) 0.041(3) 0.036(3) 0.002(2) 0.012(2) 0.001(2) C9 0.028(3) 0.040(3) 0.045(3) 0.0002(19) 0.013(2) 0.001(2) C10 0.038(3) 0.046(3) 0.052(3) -0.002(2) 0.025(3) 0.004(2) C11 0.041(3) 0.054(3) 0.052(3) -0.001(2) 0.024(3) 0.003(3) C12 0.053(3) 0.061(4) 0.063(4) -0.001(3) 0.035(3) 0.011(3) C13 0.054(3) 0.073(4) 0.052(3) -0.010(3) 0.033(3) 0.006(3) C14 0.039(3) 0.063(3) 0.040(3) -0.005(2) 0.018(2) -0.001(3) C15 0.039(3) 0.055(3) 0.044(3) -0.004(2) 0.023(2) -0.001(2) C16 0.037(3) 0.043(3) 0.053(3) 0.002(2) 0.027(3) -0.002(2) C17 0.040(3) 0.043(3) 0.048(3) 0.006(2) 0.026(3) 0.000(2) C18 0.032(3) 0.039(3) 0.041(3) 0.002(2) 0.014(2) 0.000(2) C19 0.042(3) 0.040(3) 0.047(3) 0.006(2) 0.023(3) 0.005(2) C20 0.044(3) 0.039(3) 0.048(3) 0.000(2) 0.019(3) -0.003(2) C21 0.038(3) 0.039(3) 0.052(3) 0.000(2) 0.019(3) 0.002(2) C22 0.038(3) 0.043(3) 0.052(3) 0.005(2) 0.024(3) 0.003(2) C23 0.032(3) 0.047(3) 0.042(3) -0.002(2) 0.017(2) -0.001(2) C24 0.038(3) 0.043(3) 0.045(3) 0.005(2) 0.024(3) 0.005(2) B1 0.036(3) 0.040(3) 0.048(4) -0.005(2) 0.021(3) -0.003(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle B1 O1 B1 2_655 130.6(5) C1 N2 C8 . 113.1(4) C1 N2 B1 . 123.1(4) C8 N2 B1 . 123.3(4) C9 N3 C8 . 117.3(4) C9 N4 C16 . 112.3(4) C9 N4 B1 . 123.2(4) C16 N4 B1 . 123.0(4) C16 N5 C17 . 116.3(4) C17 N6 C24 . 112.4(4) C17 N6 B1 . 123.1(4) C24 N6 B1 . 123.0(4) C24 N1 C1 . 116.3(4) N2 C1 N1 . 122.6(4) N2 C1 C2 . 106.2(4) N1 C1 C2 . 129.0(4) C3 C2 C1 . 133.0(5) C3 C2 C7 . 120.8(4) C7 C2 C1 . 106.1(4) C2 C3 H3A . 121.1 C2 C3 C4 . 117.9(5) C4 C3 H3A . 121.1 C3 C4 H4A . 119.5 C3 C4 C5 . 121.1(5) C5 C4 H4A . 119.5 C4 C5 H5A . 119.0 C6 C5 C4 . 122.0(5) C6 C5 H5A . 119.0 C5 C6 H6A . 120.9 C5 C6 C7 . 118.2(5) C7 C6 H6A . 120.9 C2 C7 C8 . 107.7(4) C6 C7 C2 . 120.1(4) C6 C7 C8 . 132.1(5) N2 C8 C7 . 105.4(4) N3 C8 N2 . 122.1(4) N3 C8 C7 . 130.6(4) N3 C9 N4 . 123.2(4) N3 C9 C10 . 128.8(4) N4 C9 C10 . 106.3(4) C11 C10 C9 . 132.3(5) C11 C10 C15 . 120.5(5) C15 C10 C9 . 107.0(4) C10 C11 H11A . 121.2 C10 C11 C12 . 117.7(5) C12 C11 H11A . 121.2 C11 C12 H12A . 119.2 C13 C12 C11 . 121.7(5) C13 C12 H12A . 119.2 C12 C13 H13A . 119.5 C14 C13 C12 . 120.9(5) C14 C13 H13A . 119.5 C13 C14 H14A . 120.8 C13 C14 C15 . 118.5(5) C15 C14 H14A . 120.8 C10 C15 C16 . 106.6(4) C14 C15 C10 . 120.8(5) C14 C15 C16 . 132.3(5) N4 C16 C15 . 106.4(4) N5 C16 N4 . 122.9(4) N5 C16 C15 . 128.6(5) N5 C17 N6 . 122.8(4) N5 C17 C18 . 128.9(4) N6 C17 C18 . 106.4(4) C19 C18 C17 . 131.0(5) C19 C18 C23 . 122.4(4) C23 C18 C17 . 106.2(4) C18 C19 H19A . 121.8 C20 C19 C18 . 116.3(5) C20 C19 H19A . 121.8 C19 C20 H20A . 119.0 C19 C20 C21 . 122.1(5) C21 C20 H20A . 119.0 C20 C21 H21A . 119.3 C22 C21 C20 . 121.5(4) C22 C21 H21A . 119.3 C21 C22 H22A . 121.2 C21 C22 C23 . 117.6(5) C23 C22 H22A . 121.2 C18 C23 C24 . 108.3(4) C22 C23 C18 . 120.0(4) C22 C23 C24 . 131.5(4) N6 C24 C23 . 105.5(4) N1 C24 N6 . 123.2(4) N1 C24 C23 . 129.7(4) O1 B1 N2 . 116.6(4) O1 B1 N4 . 118.0(4) O1 B1 N6 . 112.2(4) N2 B1 N4 . 102.6(4) N2 B1 N6 . 102.5(4) N6 B1 N4 . 102.9(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 B1 2_655 1.418(6) O1 B1 . 1.418(6) N2 C1 . 1.356(6) N2 C8 . 1.366(6) N2 B1 . 1.508(7) N3 C8 . 1.341(6) N3 C9 . 1.335(6) N4 C9 . 1.360(6) N4 C16 . 1.362(6) N4 B1 . 1.511(7) N5 C16 . 1.349(6) N5 C17 . 1.353(6) N6 C17 . 1.362(6) N6 C24 . 1.371(6) N6 B1 . 1.510(6) N1 C1 . 1.356(6) N1 C24 . 1.340(6) C1 C2 . 1.467(6) C2 C3 . 1.383(7) C2 C7 . 1.421(6) C3 H3A . 0.9500 C3 C4 . 1.389(7) C4 H4A . 0.9500 C4 C5 . 1.389(7) C5 H5A . 0.9500 C5 C6 . 1.364(7) C6 H6A . 0.9500 C6 C7 . 1.396(6) C7 C8 . 1.455(6) C9 C10 . 1.455(7) C10 C11 . 1.386(7) C10 C15 . 1.419(7) C11 H11A . 0.9500 C11 C12 . 1.392(7) C12 H12A . 0.9500 C12 C13 . 1.392(7) C13 H13A . 0.9500 C13 C14 . 1.376(7) C14 H14A . 0.9500 C14 C15 . 1.385(7) C15 C16 . 1.456(7) C17 C18 . 1.466(6) C18 C19 . 1.389(6) C18 C23 . 1.403(6) C19 H19A . 0.9500 C19 C20 . 1.385(7) C20 H20A . 0.9500 C20 C21 . 1.389(7) C21 H21A . 0.9500 C21 C22 . 1.384(7) C22 H22A . 0.9500 C22 C23 . 1.395(6) C23 C24 . 1.455(6) _journal_paper_doi 10.1107/S0108768112037184