# 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_d12289 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-Hydroxyphenolato)(subphthalocyaninato)boron ; _chemical_name_common ; m-HOPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H17 B N6 O2, 2.5(C6 H6)' _chemical_formula_sum 'C45 H32 B N6 O2' _chemical_formula_weight 699.58 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' _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 32.393(3) _cell_length_b 10.8402(12) _cell_length_c 20.303(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.286(2) _cell_angle_gamma 90.00 _cell_volume 7086.7(12) _cell_formula_units_Z 8 _cell_measurement_temperature 147(2) _cell_measurement_reflns_used 6618 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.32 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2920 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6863 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 147(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Bruker Triumph' _diffrn_measurement_device_type 'Bruker Kappa APEX-DUO CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24445 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.46 _reflns_number_total 8073 _reflns_number_gt 4968 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0582P)^2^+2.1457P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8073 _refine_ls_number_parameters 505 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1182 _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 O1 O 0.37147(4) 0.51936(12) 0.37034(7) 0.0356(3) Uani 1 1 d . . . O2 O 0.23416(4) 0.53688(14) 0.25566(8) 0.0426(4) Uani 1 1 d . . . H2O H 0.2182(7) 0.590(2) 0.2260(12) 0.064 Uiso 1 1 d . . . N1 N 0.38548(4) 0.31530(14) 0.31858(8) 0.0285(4) Uani 1 1 d . . . N2 N 0.45955(4) 0.33006(15) 0.33203(8) 0.0336(4) Uani 1 1 d . . . N3 N 0.42076(4) 0.37634(14) 0.42167(8) 0.0297(4) Uani 1 1 d . . . N4 N 0.39112(5) 0.32796(15) 0.52039(8) 0.0357(4) Uani 1 1 d . . . N5 N 0.35072(4) 0.31365(14) 0.41510(8) 0.0296(4) Uani 1 1 d . . . N6 N 0.32353(4) 0.19781(14) 0.32025(8) 0.0305(4) Uani 1 1 d . . . C1 C 0.35664(5) 0.23306(17) 0.28972(10) 0.0293(4) Uani 1 1 d . . . C2 C 0.37519(5) 0.17651(18) 0.23497(9) 0.0315(4) Uani 1 1 d . . . C3 C 0.36089(6) 0.0874(2) 0.18807(10) 0.0373(5) Uani 1 1 d . . . H3A H 0.3332 0.0578 0.1853 0.045 Uiso 1 1 calc R . . C4 C 0.38803(7) 0.0439(2) 0.14621(11) 0.0507(6) Uani 1 1 d . . . H4A H 0.3788 -0.0167 0.1141 0.061 Uiso 1 1 calc R . . C5 C 0.42911(7) 0.0868(3) 0.14957(12) 0.0564(7) Uani 1 1 d . . . H5A H 0.4470 0.0557 0.1194 0.068 Uiso 1 1 calc R . . C6 C 0.44383(6) 0.1738(2) 0.19620(11) 0.0452(6) Uani 1 1 d . . . H6A H 0.4718 0.2018 0.1989 0.054 Uiso 1 1 calc R . . C7 C 0.41691(6) 0.21900(18) 0.23867(10) 0.0332(5) Uani 1 1 d . . . C8 C 0.42350(5) 0.29978(18) 0.29579(10) 0.0323(5) Uani 1 1 d . . . C9 C 0.45767(5) 0.36084(17) 0.39565(10) 0.0321(5) Uani 1 1 d . . . C10 C 0.48927(5) 0.35302(17) 0.45233(11) 0.0353(4) Uani 1 1 d U . . C11 C 0.53239(6) 0.33763(18) 0.45705(13) 0.0447(5) Uani 1 1 d U . . H11A H 0.5468 0.3379 0.4187 0.054 Uiso 1 1 calc R . . C12 C 0.55331(6) 0.3221(2) 0.51957(14) 0.0551(6) Uani 1 1 d U . . H12A H 0.5827 0.3132 0.5241 0.066 Uiso 1 1 calc R . . C13 C 0.53262(7) 0.3191(2) 0.57582(13) 0.0560(6) Uani 1 1 d U . . H13A H 0.5482 0.3076 0.6178 0.067 Uiso 1 1 calc R . . C14 C 0.48986(7) 0.33259(19) 0.57246(12) 0.0457(5) Uani 1 1 d U . . H14A H 0.4758 0.3295 0.6111 0.055 Uiso 1 1 calc R . . C15 C 0.46830(6) 0.35089(17) 0.50998(11) 0.0356(4) Uani 1 1 d U . . C16 C 0.42379(6) 0.35870(18) 0.48840(10) 0.0329(5) Uani 1 1 d . . . C17 C 0.35567(6) 0.29867(18) 0.48249(10) 0.0333(5) Uani 1 1 d . . . C18 C 0.32176(6) 0.21972(19) 0.49796(11) 0.0353(5) Uani 1 1 d . . . C19 C 0.31020(6) 0.1775(2) 0.55803(12) 0.0445(5) Uani 1 1 d . . . H19A H 0.3242 0.2046 0.5990 0.053 Uiso 1 1 calc R . . C20 C 0.27748(7) 0.0942(2) 0.55592(13) 0.0505(6) Uani 1 1 d . . . H20A H 0.2687 0.0648 0.5962 0.061 Uiso 1 1 calc R . . C21 C 0.25714(6) 0.0527(2) 0.49537(13) 0.0489(6) Uani 1 1 d . . . H21A H 0.2348 -0.0038 0.4957 0.059 Uiso 1 1 calc R . . C22 C 0.26885(6) 0.09200(19) 0.43526(12) 0.0407(5) Uani 1 1 d . . . H22A H 0.2553 0.0618 0.3946 0.049 Uiso 1 1 calc R . . C23 C 0.30127(5) 0.17758(18) 0.43616(10) 0.0335(5) Uani 1 1 d . . . C24 C 0.32242(5) 0.23225(17) 0.38421(10) 0.0300(4) Uani 1 1 d . . . C25 C 0.34138(5) 0.57326(17) 0.32673(9) 0.0290(4) Uani 1 1 d . . . C26 C 0.30180(5) 0.52470(17) 0.31141(9) 0.0283(4) Uani 1 1 d . . . H26A H 0.2946 0.4481 0.3297 0.034 Uiso 1 1 calc R . . C27 C 0.27270(5) 0.58962(17) 0.26878(9) 0.0276(4) Uani 1 1 d . . . C28 C 0.28253(6) 0.70122(19) 0.24199(10) 0.0361(5) Uani 1 1 d . . . H28A H 0.2625 0.7448 0.2132 0.043 Uiso 1 1 calc R . . C29 C 0.32203(6) 0.7488(2) 0.25775(12) 0.0498(6) Uani 1 1 d . . . H29A H 0.3291 0.8259 0.2398 0.060 Uiso 1 1 calc R . . C30 C 0.35156(6) 0.6851(2) 0.29960(12) 0.0459(6) Uani 1 1 d . . . H30A H 0.3787 0.7183 0.3096 0.055 Uiso 1 1 calc R . . B1 B 0.37993(6) 0.3899(2) 0.37921(11) 0.0303(5) Uani 1 1 d . . . C1S C 0.41022(8) -0.0336(2) 0.35041(11) 0.0496(6) Uani 1 1 d . . . H1SA H 0.4040 -0.0599 0.3058 0.059 Uiso 1 1 calc R . . C2S C 0.38071(7) -0.0438(2) 0.39417(12) 0.0506(6) Uani 1 1 d . . . H2SA H 0.3541 -0.0768 0.3797 0.061 Uiso 1 1 calc R . . C3S C 0.38988(8) -0.0058(2) 0.45922(12) 0.0536(6) Uani 1 1 d . . . H3SA H 0.3697 -0.0134 0.4896 0.064 Uiso 1 1 calc R . . C4S C 0.42840(8) 0.0431(2) 0.47978(12) 0.0520(6) Uani 1 1 d . . . H4SA H 0.4346 0.0698 0.5243 0.062 Uiso 1 1 calc R . . C5S C 0.45786(8) 0.0534(2) 0.43642(12) 0.0514(6) Uani 1 1 d . . . H5SA H 0.4844 0.0870 0.4510 0.062 Uiso 1 1 calc R . . C6S C 0.44889(8) 0.0149(2) 0.37151(12) 0.0516(6) Uani 1 1 d . . . H6SA H 0.4693 0.0218 0.3414 0.062 Uiso 1 1 calc R . . C7S C 0.34814(7) 0.4119(3) 0.08818(15) 0.0641(8) Uani 1 1 d . . . H7SA H 0.3714 0.4638 0.0841 0.077 Uiso 1 1 calc R . . C8S C 0.32648(7) 0.4219(2) 0.14259(13) 0.0509(6) Uani 1 1 d . . . H8SA H 0.3347 0.4804 0.1763 0.061 Uiso 1 1 calc R . . C9S C 0.29302(7) 0.3469(2) 0.14772(12) 0.0483(6) Uani 1 1 d . . . H9SA H 0.2779 0.3541 0.1851 0.058 Uiso 1 1 calc R . . C10S C 0.28095(7) 0.2612(2) 0.09953(13) 0.0513(6) Uani 1 1 d . . . H10A H 0.2577 0.2096 0.1040 0.062 Uiso 1 1 calc R . . C11S C 0.30218(7) 0.2498(3) 0.04487(14) 0.0599(7) Uani 1 1 d . . . H11B H 0.2937 0.1905 0.0117 0.072 Uiso 1 1 calc R . . C12S C 0.33579(8) 0.3246(3) 0.03845(15) 0.0691(8) Uani 1 1 d . . . H12B H 0.3506 0.3174 0.0007 0.083 Uiso 1 1 calc R . . C13S C 0.43991(11) 0.2591(4) 0.71580(17) 0.0709(17) Uani 0.50 1 d PG A -1 H13B H 0.4136 0.2206 0.7062 0.085 Uiso 0.50 1 calc PR A -1 C14S C 0.44275(10) 0.3869(4) 0.71878(17) 0.0652(15) Uani 0.50 1 d PG A -1 H14B H 0.4184 0.4359 0.7112 0.078 Uiso 0.50 1 calc PR A -1 C15S C 0.48127(13) 0.4432(3) 0.73282(18) 0.0627(16) Uani 0.50 1 d PG A -1 H15A H 0.4832 0.5306 0.7349 0.075 Uiso 0.50 1 calc PR A -1 C16S C 0.51695(10) 0.3716(4) 0.74390(17) 0.0641(17) Uani 0.50 1 d PG A -1 H16A H 0.5433 0.4100 0.7535 0.077 Uiso 0.50 1 calc PR A -1 C17S C 0.51411(11) 0.2437(4) 0.74093(17) 0.0678(18) Uani 0.50 1 d PG A -1 H17A H 0.5385 0.1948 0.7485 0.081 Uiso 0.50 1 calc PR A -1 C18S C 0.47559(14) 0.1875(3) 0.72688(19) 0.0729(18) Uani 0.50 1 d PG A -1 H18A H 0.4737 0.1001 0.7249 0.088 Uiso 0.50 1 calc PR A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0282(6) 0.0199(7) 0.0531(9) -0.0010(6) -0.0211(6) 0.0009(5) O2 0.0216(6) 0.0357(8) 0.0661(10) 0.0127(8) -0.0142(6) -0.0006(6) N1 0.0224(7) 0.0204(8) 0.0394(9) 0.0013(7) -0.0122(6) -0.0031(6) N2 0.0254(8) 0.0244(9) 0.0481(11) -0.0004(8) -0.0094(7) -0.0055(6) N3 0.0234(8) 0.0198(8) 0.0421(10) -0.0035(7) -0.0134(6) 0.0005(6) N4 0.0338(9) 0.0284(9) 0.0422(10) -0.0094(8) -0.0080(7) 0.0060(7) N5 0.0218(7) 0.0218(8) 0.0425(10) -0.0026(7) -0.0091(6) 0.0021(6) N6 0.0198(7) 0.0242(9) 0.0443(10) 0.0030(7) -0.0113(6) 0.0000(6) C1 0.0245(9) 0.0213(9) 0.0378(11) 0.0033(8) -0.0153(8) -0.0015(7) C2 0.0295(9) 0.0279(10) 0.0337(11) 0.0056(9) -0.0114(8) -0.0037(8) C3 0.0350(10) 0.0367(12) 0.0374(12) 0.0020(10) -0.0089(9) -0.0084(9) C4 0.0526(13) 0.0542(16) 0.0438(13) -0.0148(12) -0.0013(10) -0.0155(12) C5 0.0502(13) 0.0676(18) 0.0527(15) -0.0193(13) 0.0110(11) -0.0162(13) C6 0.0377(11) 0.0501(14) 0.0472(13) -0.0036(11) 0.0016(10) -0.0111(10) C7 0.0308(10) 0.0294(11) 0.0370(11) 0.0038(9) -0.0074(8) -0.0055(8) C8 0.0250(9) 0.0252(10) 0.0441(12) 0.0034(9) -0.0080(8) -0.0037(8) C9 0.0227(9) 0.0197(10) 0.0502(13) -0.0019(9) -0.0120(8) -0.0026(7) C10 0.0281(9) 0.0176(9) 0.0549(11) -0.0056(9) -0.0187(8) -0.0007(8) C11 0.0256(8) 0.0254(11) 0.0777(13) -0.0067(11) -0.0184(9) -0.0012(8) C12 0.0299(10) 0.0336(12) 0.0933(15) -0.0026(13) -0.0316(9) 0.0012(9) C13 0.0474(11) 0.0343(12) 0.0754(13) 0.0026(13) -0.0433(10) 0.0001(10) C14 0.0492(10) 0.0279(11) 0.0529(11) -0.0034(10) -0.0267(9) -0.0001(9) C15 0.0317(9) 0.0184(10) 0.0511(11) -0.0059(9) -0.0204(7) 0.0014(8) C16 0.0328(10) 0.0216(10) 0.0401(12) -0.0069(9) -0.0158(8) 0.0047(8) C17 0.0309(10) 0.0250(10) 0.0420(12) -0.0061(9) -0.0053(8) 0.0076(8) C18 0.0282(10) 0.0287(11) 0.0484(13) -0.0055(10) 0.0008(8) 0.0098(8) C19 0.0408(12) 0.0423(13) 0.0513(14) -0.0023(11) 0.0092(10) 0.0131(10) C20 0.0468(13) 0.0438(14) 0.0641(16) 0.0054(12) 0.0201(11) 0.0132(11) C21 0.0326(11) 0.0394(13) 0.0761(18) 0.0049(13) 0.0120(11) 0.0050(10) C22 0.0264(10) 0.0313(11) 0.0635(15) 0.0004(11) 0.0007(9) 0.0026(8) C23 0.0222(9) 0.0257(10) 0.0513(13) -0.0011(9) -0.0025(8) 0.0050(8) C24 0.0200(8) 0.0209(9) 0.0460(12) -0.0005(9) -0.0101(8) 0.0022(7) C25 0.0241(9) 0.0219(10) 0.0380(11) -0.0027(8) -0.0109(7) 0.0046(7) C26 0.0242(8) 0.0208(10) 0.0381(11) 0.0040(8) -0.0044(7) 0.0014(7) C27 0.0194(8) 0.0253(10) 0.0366(11) -0.0012(8) -0.0037(7) 0.0026(7) C28 0.0284(9) 0.0301(11) 0.0464(12) 0.0071(9) -0.0118(8) 0.0041(8) C29 0.0371(11) 0.0345(13) 0.0736(17) 0.0209(12) -0.0135(11) -0.0069(9) C30 0.0277(10) 0.0306(12) 0.0745(16) 0.0115(11) -0.0168(10) -0.0072(9) B1 0.0229(10) 0.0224(11) 0.0420(13) -0.0015(10) -0.0128(9) -0.0005(8) C1S 0.0716(16) 0.0366(13) 0.0377(13) -0.0006(11) -0.0067(11) 0.0097(12) C2S 0.0483(13) 0.0420(14) 0.0584(15) 0.0005(12) -0.0085(11) 0.0152(11) C3S 0.0670(16) 0.0422(14) 0.0516(15) -0.0003(12) 0.0067(12) 0.0197(12) C4S 0.0811(17) 0.0316(13) 0.0396(13) -0.0012(11) -0.0097(12) 0.0084(12) C5S 0.0662(15) 0.0268(12) 0.0573(16) 0.0060(11) -0.0104(12) -0.0033(11) C6S 0.0677(16) 0.0347(13) 0.0530(15) 0.0089(11) 0.0089(12) 0.0017(11) C7S 0.0405(13) 0.0605(18) 0.089(2) 0.0240(16) -0.0014(13) -0.0109(12) C8S 0.0485(13) 0.0409(14) 0.0604(16) 0.0093(12) -0.0069(11) 0.0024(11) C9S 0.0419(12) 0.0477(15) 0.0546(15) 0.0133(12) 0.0019(10) 0.0083(11) C10S 0.0384(12) 0.0473(15) 0.0665(17) 0.0143(13) -0.0016(11) -0.0006(11) C11S 0.0520(15) 0.0556(17) 0.0696(19) -0.0027(14) -0.0039(13) 0.0062(13) C12S 0.0511(15) 0.090(2) 0.0684(19) 0.0102(17) 0.0153(13) 0.0124(15) C13S 0.082(4) 0.072(4) 0.066(4) -0.014(3) 0.039(3) -0.029(3) C14S 0.081(4) 0.063(4) 0.058(3) 0.001(3) 0.035(3) -0.006(3) C15S 0.105(5) 0.038(3) 0.052(4) -0.014(3) 0.041(3) -0.017(3) C16S 0.097(5) 0.065(4) 0.034(3) -0.009(3) 0.027(3) -0.015(3) C17S 0.106(6) 0.059(4) 0.041(4) -0.003(3) 0.020(3) 0.013(3) C18S 0.127(6) 0.043(3) 0.054(4) -0.010(3) 0.036(4) -0.024(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 O1 C25 1.373(2) . ? O1 B1 1.438(2) . ? O2 C27 1.372(2) . ? O2 H2O 0.94(3) . ? N1 C8 1.373(2) . ? N1 C1 1.375(2) . ? N1 B1 1.500(3) . ? N2 C9 1.342(3) . ? N2 C8 1.351(2) . ? N3 C16 1.361(3) . ? N3 C9 1.369(2) . ? N3 B1 1.505(2) . ? N4 C16 1.343(3) . ? N4 C17 1.348(2) . ? N5 C17 1.370(3) . ? N5 C24 1.374(2) . ? N5 B1 1.503(3) . ? N6 C1 1.351(2) . ? N6 C24 1.355(2) . ? C1 C2 1.456(3) . ? C2 C3 1.399(3) . ? C2 C7 1.422(2) . ? C3 C4 1.371(3) . ? C3 H3A 0.9500 . ? C4 C5 1.404(3) . ? C4 H4A 0.9500 . ? C5 C6 1.384(3) . ? C5 H5A 0.9500 . ? C6 C7 1.382(3) . ? C6 H6A 0.9500 . ? C7 C8 1.450(3) . ? C9 C10 1.456(2) . ? C10 C11 1.400(3) . ? C10 C15 1.416(3) . ? C11 C12 1.382(3) . ? C11 H11A 0.9500 . ? C12 C13 1.387(4) . ? C12 H12A 0.9500 . ? C13 C14 1.387(3) . ? C13 H13A 0.9500 . ? C14 C15 1.394(3) . ? C14 H14A 0.9500 . ? C15 C16 1.463(2) . ? C17 C18 1.454(3) . ? C18 C19 1.392(3) . ? C18 C23 1.429(3) . ? C19 C20 1.389(3) . ? C19 H19A 0.9500 . ? C20 C21 1.404(3) . ? C20 H20A 0.9500 . ? C21 C22 1.384(3) . ? C21 H21A 0.9500 . ? C22 C23 1.400(3) . ? C22 H22A 0.9500 . ? C23 C24 1.446(3) . ? C25 C30 1.387(3) . ? C25 C26 1.389(2) . ? C26 C27 1.398(2) . ? C26 H26A 0.9500 . ? C27 C28 1.378(3) . ? C28 C29 1.384(3) . ? C28 H28A 0.9500 . ? C29 C30 1.391(3) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C1S C2S 1.379(3) . ? C1S C6S 1.383(3) . ? C1S H1SA 0.9500 . ? C2S C3S 1.384(3) . ? C2S H2SA 0.9500 . ? C3S C4S 1.377(3) . ? C3S H3SA 0.9500 . ? C4S C5S 1.372(3) . ? C4S H4SA 0.9500 . ? C5S C6S 1.383(3) . ? C5S H5SA 0.9500 . ? C6S H6SA 0.9500 . ? C7S C8S 1.376(4) . ? C7S C12S 1.410(4) . ? C7S H7SA 0.9500 . ? C8S C9S 1.368(3) . ? C8S H8SA 0.9500 . ? C9S C10S 1.374(3) . ? C9S H9SA 0.9500 . ? C10S C11S 1.374(4) . ? C10S H10A 0.9500 . ? C11S C12S 1.375(4) . ? C11S H11B 0.9500 . ? C12S H12B 0.9500 . ? C13S C14S 1.3900 . ? C13S C18S 1.3900 . ? C13S H13B 0.9500 . ? C14S C15S 1.3900 . ? C14S H14B 0.9500 . ? C15S C16S 1.3900 . ? C15S H15A 0.9500 . ? C16S C17S 1.3900 . ? C16S H16A 0.9500 . ? C17S C18S 1.3900 . ? C17S H17A 0.9500 . ? C18S H18A 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 127.46(14) . . ? C27 O2 H2O 107.0(15) . . ? C8 N1 C1 111.70(16) . . ? C8 N1 B1 122.37(14) . . ? C1 N1 B1 124.21(16) . . ? C9 N2 C8 117.21(16) . . ? C16 N3 C9 113.32(15) . . ? C16 N3 B1 123.16(16) . . ? C9 N3 B1 122.74(17) . . ? C16 N4 C17 116.71(17) . . ? C17 N5 C24 112.28(16) . . ? C17 N5 B1 122.58(15) . . ? C24 N5 B1 123.77(17) . . ? C1 N6 C24 117.86(15) . . ? N6 C1 N1 121.61(18) . . ? N6 C1 C2 130.24(16) . . ? N1 C1 C2 106.29(16) . . ? C3 C2 C7 120.10(19) . . ? C3 C2 C1 132.60(17) . . ? C7 C2 C1 107.01(16) . . ? C4 C3 C2 118.17(18) . . ? C4 C3 H3A 120.9 . . ? C2 C3 H3A 120.9 . . ? C3 C4 C5 121.6(2) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C7 C6 C5 118.35(19) . . ? C7 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? C6 C7 C2 120.89(19) . . ? C6 C7 C8 131.71(17) . . ? C2 C7 C8 107.09(17) . . ? N2 C8 N1 122.72(18) . . ? N2 C8 C7 128.70(18) . . ? N1 C8 C7 106.53(15) . . ? N2 C9 N3 122.37(15) . . ? N2 C9 C10 130.09(18) . . ? N3 C9 C10 105.67(18) . . ? C11 C10 C15 120.44(18) . . ? C11 C10 C9 132.1(2) . . ? C15 C10 C9 107.15(16) . . ? C12 C11 C10 117.6(2) . . ? C12 C11 H11A 121.2 . . ? C10 C11 H11A 121.2 . . ? C11 C12 C13 121.8(2) . . ? C11 C12 H12A 119.1 . . ? C13 C12 H12A 119.1 . . ? C12 C13 C14 121.8(2) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C13 C14 C15 117.2(2) . . ? C13 C14 H14A 121.4 . . ? C15 C14 H14A 121.4 . . ? C14 C15 C10 121.13(18) . . ? C14 C15 C16 131.3(2) . . ? C10 C15 C16 107.31(16) . . ? N4 C16 N3 122.78(16) . . ? N4 C16 C15 130.09(18) . . ? N3 C16 C15 105.53(17) . . ? N4 C17 N5 122.77(18) . . ? N4 C17 C18 129.18(19) . . ? N5 C17 C18 106.09(16) . . ? C19 C18 C23 121.38(19) . . ? C19 C18 C17 131.69(19) . . ? C23 C18 C17 106.73(18) . . ? C20 C19 C18 117.7(2) . . ? C20 C19 H19A 121.2 . . ? C18 C19 H19A 121.2 . . ? C19 C20 C21 121.2(2) . . ? C19 C20 H20A 119.4 . . ? C21 C20 H20A 119.4 . . ? C22 C21 C20 121.7(2) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C23 118.0(2) . . ? C21 C22 H22A 121.0 . . ? C23 C22 H22A 121.0 . . ? C22 C23 C18 119.9(2) . . ? C22 C23 C24 132.58(19) . . ? C18 C23 C24 107.33(16) . . ? N6 C24 N5 121.87(17) . . ? N6 C24 C23 130.56(17) . . ? N5 C24 C23 106.03(17) . . ? O1 C25 C30 116.44(15) . . ? O1 C25 C26 123.75(17) . . ? C30 C25 C26 119.74(16) . . ? C25 C26 C27 119.42(17) . . ? C25 C26 H26A 120.3 . . ? C27 C26 H26A 120.3 . . ? O2 C27 C28 122.26(16) . . ? O2 C27 C26 116.61(17) . . ? C28 C27 C26 121.13(16) . . ? C27 C28 C29 118.93(17) . . ? C27 C28 H28A 120.5 . . ? C29 C28 H28A 120.5 . . ? C28 C29 C30 120.8(2) . . ? C28 C29 H29A 119.6 . . ? C30 C29 H29A 119.6 . . ? C25 C30 C29 119.94(18) . . ? C25 C30 H30A 120.0 . . ? C29 C30 H30A 120.0 . . ? O1 B1 N1 117.49(18) . . ? O1 B1 N5 118.42(17) . . ? N1 B1 N5 103.90(15) . . ? O1 B1 N3 108.08(15) . . ? N1 B1 N3 103.94(15) . . ? N5 B1 N3 103.25(16) . . ? C2S C1S C6S 120.0(2) . . ? C2S C1S H1SA 120.0 . . ? C6S C1S H1SA 120.0 . . ? C1S C2S C3S 120.0(2) . . ? C1S C2S H2SA 120.0 . . ? C3S C2S H2SA 120.0 . . ? C4S C3S C2S 119.7(2) . . ? C4S C3S H3SA 120.1 . . ? C2S C3S H3SA 120.1 . . ? C5S C4S C3S 120.5(2) . . ? C5S C4S H4SA 119.7 . . ? C3S C4S H4SA 119.7 . . ? C4S C5S C6S 119.9(2) . . ? C4S C5S H5SA 120.1 . . ? C6S C5S H5SA 120.1 . . ? C5S C6S C1S 119.9(2) . . ? C5S C6S H6SA 120.0 . . ? C1S C6S H6SA 120.0 . . ? C8S C7S C12S 119.9(2) . . ? C8S C7S H7SA 120.1 . . ? C12S C7S H7SA 120.1 . . ? C9S C8S C7S 119.5(2) . . ? C9S C8S H8SA 120.3 . . ? C7S C8S H8SA 120.3 . . ? C8S C9S C10S 120.9(2) . . ? C8S C9S H9SA 119.6 . . ? C10S C9S H9SA 119.6 . . ? C11S C10S C9S 120.5(2) . . ? C11S C10S H10A 119.7 . . ? C9S C10S H10A 119.7 . . ? C10S C11S C12S 119.7(3) . . ? C10S C11S H11B 120.2 . . ? C12S C11S H11B 120.2 . . ? C11S C12S C7S 119.6(3) . . ? C11S C12S H12B 120.2 . . ? C7S C12S H12B 120.2 . . ? C14S C13S C18S 120.0 . . ? C14S C13S H13B 120.0 . . ? C18S C13S H13B 120.0 . . ? C13S C14S C15S 120.0 . . ? C13S C14S H14B 120.0 . . ? C15S C14S H14B 120.0 . . ? C16S C15S C14S 120.0 . . ? C16S C15S H15A 120.0 . . ? C14S C15S H15A 120.0 . . ? C15S C16S C17S 120.0 . . ? C15S C16S H16A 120.0 . . ? C17S C16S H16A 120.0 . . ? C16S C17S C18S 120.0 . . ? C16S C17S H17A 120.0 . . ? C18S C17S H17A 120.0 . . ? C17S C18S C13S 120.0 . . ? C17S C18S H18A 120.0 . . ? C13S C18S H18A 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 N6 C1 N1 -9.0(2) . . . . ? C24 N6 C1 C2 153.17(18) . . . . ? C8 N1 C1 N6 154.25(16) . . . . ? B1 N1 C1 N6 -11.0(3) . . . . ? C8 N1 C1 C2 -11.7(2) . . . . ? B1 N1 C1 C2 -176.96(16) . . . . ? N6 C1 C2 C3 15.9(3) . . . . ? N1 C1 C2 C3 -179.9(2) . . . . ? N6 C1 C2 C7 -157.78(18) . . . . ? N1 C1 C2 C7 6.5(2) . . . . ? C7 C2 C3 C4 -0.5(3) . . . . ? C1 C2 C3 C4 -173.4(2) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C4 C5 C6 C7 -1.0(4) . . . . ? C5 C6 C7 C2 0.5(3) . . . . ? C5 C6 C7 C8 173.2(2) . . . . ? C3 C2 C7 C6 0.3(3) . . . . ? C1 C2 C7 C6 174.88(19) . . . . ? C3 C2 C7 C8 -174.06(17) . . . . ? C1 C2 C7 C8 0.5(2) . . . . ? C9 N2 C8 N1 9.0(3) . . . . ? C9 N2 C8 C7 -152.5(2) . . . . ? C1 N1 C8 N2 -152.96(17) . . . . ? B1 N1 C8 N2 12.6(3) . . . . ? C1 N1 C8 C7 12.0(2) . . . . ? B1 N1 C8 C7 177.64(16) . . . . ? C6 C7 C8 N2 -17.1(4) . . . . ? C2 C7 C8 N2 156.42(19) . . . . ? C6 C7 C8 N1 179.1(2) . . . . ? C2 C7 C8 N1 -7.4(2) . . . . ? C8 N2 C9 N3 -7.9(3) . . . . ? C8 N2 C9 C10 154.2(2) . . . . ? C16 N3 C9 N2 155.42(18) . . . . ? B1 N3 C9 N2 -14.7(3) . . . . ? C16 N3 C9 C10 -10.5(2) . . . . ? B1 N3 C9 C10 179.37(16) . . . . ? N2 C9 C10 C11 15.8(4) . . . . ? N3 C9 C10 C11 -179.8(2) . . . . ? N2 C9 C10 C15 -158.1(2) . . . . ? N3 C9 C10 C15 6.3(2) . . . . ? C15 C10 C11 C12 -0.8(3) . . . . ? C9 C10 C11 C12 -174.0(2) . . . . ? C10 C11 C12 C13 1.3(3) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C13 C14 C15 C10 1.3(3) . . . . ? C13 C14 C15 C16 174.6(2) . . . . ? C11 C10 C15 C14 -0.5(3) . . . . ? C9 C10 C15 C14 174.20(18) . . . . ? C11 C10 C15 C16 -175.27(17) . . . . ? C9 C10 C15 C16 -0.6(2) . . . . ? C17 N4 C16 N3 8.7(3) . . . . ? C17 N4 C16 C15 -154.69(19) . . . . ? C9 N3 C16 N4 -156.77(17) . . . . ? B1 N3 C16 N4 13.3(3) . . . . ? C9 N3 C16 C15 10.1(2) . . . . ? B1 N3 C16 C15 -179.80(16) . . . . ? C14 C15 C16 N4 -14.0(4) . . . . ? C10 C15 C16 N4 160.1(2) . . . . ? C14 C15 C16 N3 -179.5(2) . . . . ? C10 C15 C16 N3 -5.5(2) . . . . ? C16 N4 C17 N5 -8.1(3) . . . . ? C16 N4 C17 C18 153.7(2) . . . . ? C24 N5 C17 N4 152.61(17) . . . . ? B1 N5 C17 N4 -14.4(3) . . . . ? C24 N5 C17 C18 -12.8(2) . . . . ? B1 N5 C17 C18 -179.85(16) . . . . ? N4 C17 C18 C19 18.5(4) . . . . ? N5 C17 C18 C19 -177.3(2) . . . . ? N4 C17 C18 C23 -156.23(19) . . . . ? N5 C17 C18 C23 7.9(2) . . . . ? C23 C18 C19 C20 -1.1(3) . . . . ? C17 C18 C19 C20 -175.2(2) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? C19 C20 C21 C22 0.4(3) . . . . ? C20 C21 C22 C23 -1.5(3) . . . . ? C21 C22 C23 C18 1.3(3) . . . . ? C21 C22 C23 C24 176.31(19) . . . . ? C19 C18 C23 C22 0.0(3) . . . . ? C17 C18 C23 C22 175.40(17) . . . . ? C19 C18 C23 C24 -176.18(18) . . . . ? C17 C18 C23 C24 -0.8(2) . . . . ? C1 N6 C24 N5 8.5(2) . . . . ? C1 N6 C24 C23 -155.21(18) . . . . ? C17 N5 C24 N6 -154.91(16) . . . . ? B1 N5 C24 N6 12.0(3) . . . . ? C17 N5 C24 C23 12.3(2) . . . . ? B1 N5 C24 C23 179.19(15) . . . . ? C22 C23 C24 N6 -16.4(3) . . . . ? C18 C23 C24 N6 159.04(18) . . . . ? C22 C23 C24 N5 177.88(19) . . . . ? C18 C23 C24 N5 -6.6(2) . . . . ? B1 O1 C25 C30 -145.1(2) . . . . ? B1 O1 C25 C26 37.9(3) . . . . ? O1 C25 C26 C27 176.94(18) . . . . ? C30 C25 C26 C27 -0.1(3) . . . . ? C25 C26 C27 O2 -179.93(17) . . . . ? C25 C26 C27 C28 -0.4(3) . . . . ? O2 C27 C28 C29 179.7(2) . . . . ? C26 C27 C28 C29 0.2(3) . . . . ? C27 C28 C29 C30 0.4(4) . . . . ? O1 C25 C30 C29 -176.6(2) . . . . ? C26 C25 C30 C29 0.6(3) . . . . ? C28 C29 C30 C25 -0.8(4) . . . . ? C25 O1 B1 N1 51.3(3) . . . . ? C25 O1 B1 N5 -74.8(3) . . . . ? C25 O1 B1 N3 168.40(17) . . . . ? C8 N1 B1 O1 89.7(2) . . . . ? C1 N1 B1 O1 -106.5(2) . . . . ? C8 N1 B1 N5 -137.36(16) . . . . ? C1 N1 B1 N5 26.4(2) . . . . ? C8 N1 B1 N3 -29.6(2) . . . . ? C1 N1 B1 N3 134.16(17) . . . . ? C17 N5 B1 O1 -88.8(2) . . . . ? C24 N5 B1 O1 105.6(2) . . . . ? C17 N5 B1 N1 138.78(16) . . . . ? C24 N5 B1 N1 -26.8(2) . . . . ? C17 N5 B1 N3 30.5(2) . . . . ? C24 N5 B1 N3 -135.04(16) . . . . ? C16 N3 B1 O1 96.1(2) . . . . ? C9 N3 B1 O1 -94.7(2) . . . . ? C16 N3 B1 N1 -138.39(17) . . . . ? C9 N3 B1 N1 30.8(2) . . . . ? C16 N3 B1 N5 -30.2(2) . . . . ? C9 N3 B1 N5 139.02(17) . . . . ? C6S C1S C2S C3S -0.2(3) . . . . ? C1S C2S C3S C4S 0.6(3) . . . . ? C2S C3S C4S C5S -0.5(3) . . . . ? C3S C4S C5S C6S 0.2(3) . . . . ? C4S C5S C6S C1S 0.2(3) . . . . ? C2S C1S C6S C5S -0.2(3) . . . . ? C12S C7S C8S C9S -0.2(4) . . . . ? C7S C8S C9S C10S 0.5(3) . . . . ? C8S C9S C10S C11S -0.4(3) . . . . ? C9S C10S C11S C12S 0.1(4) . . . . ? C10S C11S C12S C7S 0.2(4) . . . . ? C8S C7S C12S C11S -0.1(4) . . . . ? C18S C13S C14S C15S 0.0 . . . . ? C13S C14S C15S C16S 0.0 . . . . ? C14S C15S C16S C17S 0.0 . . . . ? C15S C16S C17S C18S 0.0 . . . . ? C16S C17S C18S C13S 0.0 . . . . ? C14S C13S C18S C17S 0.0 . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O N6 0.94(3) 1.95(3) 2.878(2) 167(2) 4 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.744 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.043 _iucr_refine_instructions_details ; TITL mo_d12289_0m in C2/c CELL 0.71073 32.3931 10.8402 20.3035 90.000 96.286 90.000 ZERR 8.00 0.0030 0.0012 0.0020 0.000 0.002 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H N O B UNIT 360 256 48 16 8 TEMP -126.180 SIZE 0.150 0.230 0.370 OMIT 2 0 0 ACTA L.S. 4 FMAP 2 PLAN 20 EQIV $1 -x+1/2, y+1/2, -z+1/2 HTAB O2 N6_$1 DELU 0.002 C10 > C15 HTAB BOND $H CONF WGHT 0.058200 2.145700 FVAR 0.06161 O1 4 0.371469 0.519363 0.370336 11.00000 0.02821 0.01988 = 0.05313 -0.00097 -0.02109 0.00094 O2 4 0.234161 0.536879 0.255656 11.00000 0.02159 0.03575 = 0.06612 0.01268 -0.01422 -0.00061 H2O 2 0.218251 0.589951 0.225922 11.00000 -1.50000 N1 3 0.385481 0.315298 0.318581 11.00000 0.02241 0.02035 = 0.03941 0.00132 -0.01221 -0.00311 N2 3 0.459548 0.330062 0.332033 11.00000 0.02536 0.02442 = 0.04810 -0.00037 -0.00941 -0.00545 N3 3 0.420762 0.376337 0.421668 11.00000 0.02338 0.01976 = 0.04208 -0.00353 -0.01337 0.00048 N4 3 0.391116 0.327964 0.520388 11.00000 0.03383 0.02839 = 0.04217 -0.00937 -0.00795 0.00602 N5 3 0.350725 0.313655 0.415096 11.00000 0.02178 0.02182 = 0.04253 -0.00264 -0.00906 0.00210 N6 3 0.323531 0.197811 0.320251 11.00000 0.01975 0.02416 = 0.04426 0.00300 -0.01128 0.00002 C1 1 0.356639 0.233063 0.289718 11.00000 0.02453 0.02128 = 0.03781 0.00330 -0.01529 -0.00154 C2 1 0.375190 0.176508 0.234969 11.00000 0.02946 0.02789 = 0.03373 0.00561 -0.01138 -0.00369 C3 1 0.360893 0.087374 0.188069 11.00000 0.03496 0.03669 = 0.03743 0.00198 -0.00895 -0.00843 AFIX 43 H3A 2 0.333152 0.057782 0.185305 11.00000 -1.20000 AFIX 0 C4 1 0.388032 0.043916 0.146205 11.00000 0.05258 0.05415 = 0.04380 -0.01483 -0.00131 -0.01550 AFIX 43 H4A 2 0.378810 -0.016711 0.114137 11.00000 -1.20000 AFIX 0 C5 1 0.429109 0.086804 0.149566 11.00000 0.05016 0.06762 = 0.05268 -0.01926 0.01096 -0.01623 AFIX 43 H5A 2 0.447025 0.055676 0.119442 11.00000 -1.20000 AFIX 0 C6 1 0.443831 0.173845 0.196201 11.00000 0.03774 0.05005 = 0.04719 -0.00364 0.00156 -0.01114 AFIX 43 H6A 2 0.471756 0.201845 0.198939 11.00000 -1.20000 AFIX 0 C7 1 0.416907 0.219003 0.238674 11.00000 0.03076 0.02936 = 0.03701 0.00376 -0.00739 -0.00551 C8 1 0.423503 0.299784 0.295789 11.00000 0.02495 0.02519 = 0.04406 0.00337 -0.00801 -0.00371 C9 1 0.457667 0.360838 0.395654 11.00000 0.02272 0.01975 = 0.05021 -0.00189 -0.01200 -0.00256 C10 1 0.489266 0.353020 0.452329 11.00000 0.02812 0.01764 = 0.05490 -0.00560 -0.01875 -0.00067 C11 1 0.532393 0.337629 0.457055 11.00000 0.02565 0.02537 = 0.07770 -0.00670 -0.01841 -0.00115 AFIX 43 H11A 2 0.546759 0.337865 0.418695 11.00000 -1.20000 AFIX 0 C12 1 0.553311 0.322077 0.519565 11.00000 0.02986 0.03356 = 0.09335 -0.00257 -0.03161 0.00123 AFIX 43 H12A 2 0.582660 0.313167 0.524112 11.00000 -1.20000 AFIX 0 C13 1 0.532621 0.319129 0.575821 11.00000 0.04736 0.03427 = 0.07535 0.00260 -0.04332 0.00012 AFIX 43 H13A 2 0.548161 0.307573 0.617828 11.00000 -1.20000 AFIX 0 C14 1 0.489855 0.332587 0.572457 11.00000 0.04916 0.02790 = 0.05291 -0.00345 -0.02665 -0.00008 AFIX 43 H14A 2 0.475839 0.329457 0.611148 11.00000 -1.20000 AFIX 0 C15 1 0.468305 0.350888 0.509979 11.00000 0.03167 0.01837 = 0.05110 -0.00593 -0.02038 0.00137 C16 1 0.423795 0.358697 0.488396 11.00000 0.03277 0.02160 = 0.04008 -0.00691 -0.01579 0.00471 C17 1 0.355669 0.298669 0.482492 11.00000 0.03086 0.02502 = 0.04197 -0.00606 -0.00534 0.00764 C18 1 0.321762 0.219725 0.497959 11.00000 0.02817 0.02867 = 0.04843 -0.00547 0.00084 0.00975 C19 1 0.310204 0.177479 0.558035 11.00000 0.04080 0.04228 = 0.05134 -0.00234 0.00916 0.01307 AFIX 43 H19A 2 0.324199 0.204623 0.599038 11.00000 -1.20000 AFIX 0 C20 1 0.277477 0.094218 0.555915 11.00000 0.04677 0.04380 = 0.06410 0.00537 0.02008 0.01319 AFIX 43 H20A 2 0.268697 0.064820 0.596203 11.00000 -1.20000 AFIX 0 C21 1 0.257145 0.052723 0.495371 11.00000 0.03257 0.03939 = 0.07608 0.00487 0.01196 0.00499 AFIX 43 H21A 2 0.234757 -0.003815 0.495653 11.00000 -1.20000 AFIX 0 C22 1 0.268852 0.092004 0.435260 11.00000 0.02637 0.03126 = 0.06347 0.00041 0.00066 0.00257 AFIX 43 H22A 2 0.255287 0.061786 0.394598 11.00000 -1.20000 AFIX 0 C23 1 0.301273 0.177581 0.436165 11.00000 0.02216 0.02567 = 0.05135 -0.00109 -0.00252 0.00498 C24 1 0.322420 0.232253 0.384209 11.00000 0.01999 0.02087 = 0.04600 -0.00051 -0.01008 0.00222 C25 1 0.341383 0.573255 0.326732 11.00000 0.02409 0.02186 = 0.03802 -0.00266 -0.01093 0.00464 C26 1 0.301799 0.524703 0.311410 11.00000 0.02421 0.02080 = 0.03805 0.00401 -0.00435 0.00142 AFIX 43 H26A 2 0.294575 0.448068 0.329742 11.00000 -1.20000 AFIX 0 C27 1 0.272696 0.589616 0.268779 11.00000 0.01942 0.02531 = 0.03658 -0.00118 -0.00372 0.00261 C28 1 0.282526 0.701219 0.241989 11.00000 0.02837 0.03011 = 0.04641 0.00709 -0.01184 0.00414 AFIX 43 H28A 2 0.262517 0.744788 0.213168 11.00000 -1.20000 AFIX 0 C29 1 0.322029 0.748826 0.257750 11.00000 0.03715 0.03446 = 0.07356 0.02092 -0.01351 -0.00691 AFIX 43 H29A 2 0.329061 0.825950 0.239760 11.00000 -1.20000 AFIX 0 C30 1 0.351561 0.685148 0.299605 11.00000 0.02766 0.03061 = 0.07451 0.01152 -0.01677 -0.00719 AFIX 43 H30A 2 0.378673 0.718291 0.309590 11.00000 -1.20000 AFIX 0 B1 5 0.379928 0.389851 0.379212 11.00000 0.02293 0.02240 = 0.04196 -0.00147 -0.01283 -0.00046 C1S 1 0.410219 -0.033570 0.350411 11.00000 0.07160 0.03658 = 0.03772 -0.00058 -0.00671 0.00970 AFIX 43 H1SA 2 0.403983 -0.059850 0.305795 11.00000 -1.20000 AFIX 0 C2S 1 0.380708 -0.043765 0.394175 11.00000 0.04826 0.04202 = 0.05837 0.00047 -0.00850 0.01523 AFIX 43 H2SA 2 0.354098 -0.076835 0.379689 11.00000 -1.20000 AFIX 0 C3S 1 0.389878 -0.005790 0.459217 11.00000 0.06703 0.04219 = 0.05164 -0.00033 0.00667 0.01970 AFIX 43 H3SA 2 0.369684 -0.013386 0.489562 11.00000 -1.20000 AFIX 0 C4S 1 0.428395 0.043058 0.479780 11.00000 0.08106 0.03158 = 0.03964 -0.00116 -0.00969 0.00840 AFIX 43 H4SA 2 0.434606 0.069772 0.524326 11.00000 -1.20000 AFIX 0 C5S 1 0.457865 0.053434 0.436420 11.00000 0.06616 0.02684 = 0.05730 0.00599 -0.01043 -0.00333 AFIX 43 H5SA 2 0.484388 0.087022 0.450978 11.00000 -1.20000 AFIX 0 C6S 1 0.448895 0.014930 0.371514 11.00000 0.06766 0.03474 = 0.05303 0.00894 0.00888 0.00170 AFIX 43 H6SA 2 0.469280 0.021785 0.341447 11.00000 -1.20000 AFIX 0 C7S 1 0.348139 0.411892 0.088177 11.00000 0.04050 0.06051 = 0.08933 0.02397 -0.00137 -0.01085 AFIX 43 H7SA 2 0.371368 0.463752 0.084137 11.00000 -1.20000 AFIX 0 C8S 1 0.326481 0.421885 0.142594 11.00000 0.04855 0.04093 = 0.06037 0.00925 -0.00694 0.00241 AFIX 43 H8SA 2 0.334706 0.480402 0.176328 11.00000 -1.20000 AFIX 0 C9S 1 0.293017 0.346884 0.147721 11.00000 0.04189 0.04768 = 0.05458 0.01326 0.00190 0.00829 AFIX 43 H9SA 2 0.277920 0.354106 0.185099 11.00000 -1.20000 AFIX 0 C10S 1 0.280949 0.261240 0.099529 11.00000 0.03842 0.04726 = 0.06652 0.01428 -0.00156 -0.00063 AFIX 43 H10A 2 0.257743 0.209553 0.104043 11.00000 -1.20000 AFIX 0 C11S 1 0.302185 0.249793 0.044875 11.00000 0.05203 0.05562 = 0.06959 -0.00271 -0.00394 0.00622 AFIX 43 H11B 2 0.293691 0.190497 0.011680 11.00000 -1.20000 AFIX 0 C12S 1 0.335789 0.324567 0.038450 11.00000 0.05112 0.08972 = 0.06844 0.01020 0.01533 0.01239 AFIX 43 H12B 2 0.350591 0.317431 0.000740 11.00000 -1.20000 PART -1 AFIX 66 C13S 1 0.439913 0.259084 0.715804 10.50000 0.08177 0.07153 = 0.06609 -0.01353 0.03883 -0.02914 AFIX 43 H13B 2 0.413587 0.220641 0.706202 10.50000 -1.20000 AFIX 65 C14S 1 0.442754 0.386948 0.718775 10.50000 0.08053 0.06330 = 0.05777 0.00057 0.03486 -0.00556 AFIX 43 H14B 2 0.418369 0.435894 0.711204 10.50000 -1.20000 AFIX 65 C15S 1 0.481273 0.443195 0.732824 10.50000 0.10519 0.03788 = 0.05218 -0.01366 0.04109 -0.01739 AFIX 43 H15A 2 0.483214 0.530585 0.734854 10.50000 -1.20000 AFIX 65 C16S 1 0.516952 0.371580 0.743901 10.50000 0.09743 0.06513 = 0.03426 -0.00890 0.02737 -0.01531 AFIX 43 H16A 2 0.543278 0.410023 0.753503 10.50000 -1.20000 AFIX 65 C17S 1 0.514111 0.243716 0.740930 10.50000 0.10578 0.05897 = 0.04126 -0.00253 0.01989 0.01267 AFIX 43 H17A 2 0.538496 0.194770 0.748501 10.50000 -1.20000 AFIX 65 C18S 1 0.475593 0.187466 0.726881 10.50000 0.12715 0.04316 = 0.05431 -0.00979 0.03601 -0.02426 AFIX 43 H18A 2 0.473651 0.100077 0.724850 10.50000 -1.20000 PART 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_d12289_0m in C2/c REM R1 = 0.0520 for 4968 Fo > 4sig(Fo) and 0.0977 for all 8073 data REM 505 parameters refined using 12 restraints END WGHT 0.0580 2.2268 REM Highest difference peak 0.744, deepest hole -0.220, 1-sigma level 0.043 Q1 1 0.2591 0.0578 0.6076 11.00000 0.05 0.74 Q2 1 0.3878 -0.1113 0.1235 11.00000 0.05 0.27 Q3 1 0.2228 -0.0149 0.5208 11.00000 0.05 0.24 Q4 1 0.3301 0.2370 0.6188 11.00000 0.05 0.23 Q5 1 0.3592 0.2182 0.2481 11.00000 0.05 0.21 Q6 1 0.4648 -0.0126 0.1267 11.00000 0.05 0.20 Q7 1 0.4477 0.3539 0.5099 11.00000 0.05 0.20 Q8 1 0.3509 0.3935 0.0472 11.00000 0.05 0.20 Q9 1 0.3084 0.2239 0.5253 11.00000 0.05 0.18 Q10 1 0.4643 0.2415 0.7288 11.00000 0.05 0.17 Q11 1 0.3561 0.3750 0.3961 11.00000 0.05 0.17 Q12 1 0.3803 0.3687 0.3406 11.00000 0.05 0.17 Q13 1 0.3362 0.3079 -0.0310 11.00000 0.05 0.16 Q14 1 0.3963 0.1905 0.2359 11.00000 0.05 0.16 Q15 1 0.3390 0.8207 0.2121 11.00000 0.05 0.16 Q16 1 0.3819 0.5408 0.3296 11.00000 0.05 0.15 Q17 1 0.4590 0.3382 0.6259 11.00000 0.05 0.15 Q18 1 0.5000 0.2877 0.7500 10.50000 0.05 0.15 Q19 1 0.2945 0.1101 0.4351 11.00000 0.05 0.15 Q20 1 0.3896 0.6886 0.2775 11.00000 0.05 0.15 ; _vrf_PLAT097_d12289 ; PROBLEM: Large Reported Max. (Positive) Residual Density 0.74 eA-3 RESPONSE: Top five peaks from the final difference Fourier are listed below. The largest peak of 0.74e/\%A is 0.41\%A H20A and has no chemical significance. Q1 1 0.2591 0.0578 0.6076 11.00000 0.05 0.74 Q2 1 0.3878 -0.1113 0.1235 11.00000 0.05 0.27 Q3 1 0.2228 -0.0149 0.5208 11.00000 0.05 0.24 Q4 1 0.3301 0.2370 0.6188 11.00000 0.05 0.23 Q5 1 0.3592 0.2182 0.2481 11.00000 0.05 0.21 ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 949038' ####################################################################### # # 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_d12137 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-Hydroxyphenolato)(subphthalocyaninato)boron ; _chemical_name_common ; p-HOPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H17 B N6 O2, C7 H8' _chemical_formula_sum 'C37 H25 B N6 O2' _chemical_formula_weight 596.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.2110(11) _cell_length_b 9.4838(6) _cell_length_c 20.4044(14) _cell_angle_alpha 90.00 _cell_angle_beta 110.991(4) _cell_angle_gamma 90.00 _cell_volume 2928.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 147(2) _cell_measurement_reflns_used 9934 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 66.59 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.687 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6822 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 147(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18659 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 66.58 _reflns_number_total 5000 _reflns_number_gt 4510 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0404P)^2^+0.9463P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5000 _refine_ls_number_parameters 420 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 O1 O 0.42327(6) 0.42689(9) 0.04669(4) 0.0282(2) Uani 1 1 d . . . O2 O 0.63957(6) 0.51713(11) 0.32368(5) 0.0355(2) Uani 1 1 d . . . N1 N 0.27873(7) 0.45081(11) -0.04536(5) 0.0252(2) Uani 1 1 d . . . N2 N 0.30432(7) 0.60986(11) -0.12651(5) 0.0264(2) Uani 1 1 d . . . N3 N 0.35883(6) 0.66095(11) -0.00447(5) 0.0233(2) Uani 1 1 d . . . N4 N 0.34575(6) 0.77429(11) 0.09492(5) 0.0242(2) Uani 1 1 d . . . N5 N 0.29727(7) 0.53879(11) 0.06690(5) 0.0249(2) Uani 1 1 d . . . N6 N 0.19053(7) 0.36097(12) 0.01672(6) 0.0300(3) Uani 1 1 d . . . C1 C 0.21087(8) 0.37006(13) -0.04154(7) 0.0275(3) Uani 1 1 d . . . C2 C 0.15782(9) 0.33425(14) -0.11392(7) 0.0291(3) Uani 1 1 d . . . C3 C 0.08175(9) 0.25302(15) -0.14355(8) 0.0351(3) Uani 1 1 d . . . H3A H 0.0577 0.2009 -0.1149 0.042 Uiso 1 1 calc R . . C4 C 0.04232(9) 0.25060(16) -0.21599(8) 0.0394(4) Uani 1 1 d . . . H4A H -0.0088 0.1943 -0.2371 0.047 Uiso 1 1 calc R . . C5 C 0.07583(9) 0.32878(16) -0.25873(7) 0.0384(3) Uani 1 1 d . . . H5A H 0.0464 0.3260 -0.3082 0.046 Uiso 1 1 calc R . . C6 C 0.15092(9) 0.41017(15) -0.23051(7) 0.0333(3) Uani 1 1 d . . . H6A H 0.1735 0.4634 -0.2598 0.040 Uiso 1 1 calc R . . C7 C 0.19262(8) 0.41189(14) -0.15761(7) 0.0281(3) Uani 1 1 d . . . C8 C 0.26671(8) 0.49324(13) -0.11198(6) 0.0256(3) Uani 1 1 d . . . C9 C 0.34684(8) 0.69515(14) -0.07250(6) 0.0248(3) Uani 1 1 d . . . C10 C 0.36683(8) 0.84475(14) -0.07210(6) 0.0257(3) Uani 1 1 d . . . C11 C 0.37071(9) 0.93503(15) -0.12448(7) 0.0326(3) Uani 1 1 d . . . H11A H 0.3635 0.9007 -0.1700 0.039 Uiso 1 1 calc R . . C12 C 0.38552(10) 1.07674(15) -0.10817(7) 0.0378(3) Uani 1 1 d . . . H12A H 0.3894 1.1403 -0.1430 0.045 Uiso 1 1 calc R . . C13 C 0.39497(9) 1.12862(15) -0.04171(7) 0.0350(3) Uani 1 1 d . . . H13A H 0.4048 1.2265 -0.0324 0.042 Uiso 1 1 calc R . . C14 C 0.39027(8) 1.04014(14) 0.01067(7) 0.0294(3) Uani 1 1 d . . . H14A H 0.3957 1.0760 0.0555 0.035 Uiso 1 1 calc R . . C15 C 0.37733(8) 0.89666(14) -0.00427(6) 0.0254(3) Uani 1 1 d . . . C16 C 0.36555(8) 0.77747(13) 0.03628(6) 0.0236(3) Uani 1 1 d . . . C17 C 0.30730(8) 0.65627(13) 0.10731(6) 0.0243(3) Uani 1 1 d . . . C18 C 0.25385(8) 0.63253(14) 0.15023(6) 0.0272(3) Uani 1 1 d . . . C19 C 0.24019(9) 0.71259(15) 0.20248(6) 0.0305(3) Uani 1 1 d . . . H19A H 0.2711 0.7985 0.2182 0.037 Uiso 1 1 calc R . . C20 C 0.18012(10) 0.66302(16) 0.23078(7) 0.0372(3) Uani 1 1 d . . . H20A H 0.1704 0.7151 0.2671 0.045 Uiso 1 1 calc R . . C21 C 0.13330(10) 0.53775(17) 0.20709(8) 0.0418(4) Uani 1 1 d . . . H21A H 0.0923 0.5069 0.2276 0.050 Uiso 1 1 calc R . . C22 C 0.14532(10) 0.45801(16) 0.15471(7) 0.0369(3) Uani 1 1 d . . . H22A H 0.1127 0.3737 0.1386 0.044 Uiso 1 1 calc R . . C23 C 0.20652(9) 0.50458(14) 0.12627(6) 0.0294(3) Uani 1 1 d . . . C24 C 0.23138(8) 0.45174(14) 0.06909(6) 0.0277(3) Uani 1 1 d . . . C25 C 0.47690(8) 0.44945(13) 0.11640(6) 0.0254(3) Uani 1 1 d . . . C26 C 0.53313(8) 0.56445(14) 0.13519(7) 0.0277(3) Uani 1 1 d . . . H26A H 0.5351 0.6292 0.1003 0.033 Uiso 1 1 calc R . . C27 C 0.58658(8) 0.58560(14) 0.20472(7) 0.0277(3) Uani 1 1 d . . . H27A H 0.6248 0.6650 0.2173 0.033 Uiso 1 1 calc R . . C28 C 0.58443(8) 0.49148(14) 0.25579(6) 0.0271(3) Uani 1 1 d . . . C29 C 0.52828(9) 0.37612(15) 0.23703(7) 0.0345(3) Uani 1 1 d . . . H29A H 0.5265 0.3110 0.2719 0.041 Uiso 1 1 calc R . . C30 C 0.47460(9) 0.35552(14) 0.16735(7) 0.0329(3) Uani 1 1 d . . . H30A H 0.4361 0.2764 0.1547 0.039 Uiso 1 1 calc R . . B1 B 0.34637(9) 0.51431(15) 0.01844(7) 0.0250(3) Uani 1 1 d . . . C1S C 0.11579(9) 0.90081(18) 0.02436(7) 0.0408(4) Uani 1 1 d . . . C2S C 0.07976(10) 0.76699(19) 0.01776(9) 0.0480(4) Uani 1 1 d . . . H2SA H 0.0557 0.7345 0.0512 0.058 Uiso 1 1 calc R . . C3S C 0.07847(12) 0.6798(2) -0.03717(10) 0.0617(5) Uani 1 1 d . . . H3SA H 0.0539 0.5878 -0.0412 0.074 Uiso 1 1 calc R . . C4S C 0.11299(13) 0.7268(3) -0.08594(9) 0.0683(7) Uani 1 1 d . . . H4SA H 0.1123 0.6676 -0.1237 0.082 Uiso 1 1 calc R . . C5S C 0.14826(12) 0.8595(3) -0.07946(9) 0.0632(6) Uani 1 1 d . . . H5SA H 0.1717 0.8924 -0.1132 0.076 Uiso 1 1 calc R . . C6S C 0.15012(10) 0.9447(2) -0.02522(8) 0.0503(4) Uani 1 1 d . . . H6SA H 0.1755 1.0361 -0.0214 0.060 Uiso 1 1 calc R . . C7S C 0.11831(13) 0.9964(2) 0.08377(9) 0.0668(6) Uani 1 1 d . . . H7SA H 0.0885 0.9504 0.1122 0.100 Uiso 1 1 calc R . . H7SB H 0.0881 1.0850 0.0648 0.100 Uiso 1 1 calc R . . H7SC H 0.1799 1.0159 0.1130 0.100 Uiso 1 1 calc R . . H1O H 0.6414(12) 0.437(2) 0.3507(10) 0.056(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0298(5) 0.0284(5) 0.0218(4) -0.0026(4) 0.0036(4) 0.0050(4) O2 0.0419(5) 0.0329(5) 0.0229(5) 0.0040(4) 0.0009(4) -0.0042(4) N1 0.0271(5) 0.0242(5) 0.0215(5) -0.0021(4) 0.0055(4) 0.0003(4) N2 0.0282(5) 0.0281(6) 0.0221(5) -0.0043(4) 0.0082(4) -0.0003(5) N3 0.0237(5) 0.0252(5) 0.0195(5) -0.0024(4) 0.0058(4) -0.0003(4) N4 0.0230(5) 0.0276(6) 0.0188(5) -0.0015(4) 0.0036(4) 0.0003(4) N5 0.0263(5) 0.0261(5) 0.0201(5) 0.0000(4) 0.0054(4) -0.0005(4) N6 0.0338(6) 0.0271(6) 0.0271(6) -0.0009(5) 0.0085(5) -0.0031(5) C1 0.0291(6) 0.0232(6) 0.0277(7) -0.0013(5) 0.0073(5) -0.0014(5) C2 0.0296(7) 0.0261(7) 0.0289(7) -0.0065(5) 0.0072(5) 0.0006(5) C3 0.0313(7) 0.0337(7) 0.0385(8) -0.0096(6) 0.0104(6) -0.0039(6) C4 0.0291(7) 0.0433(8) 0.0402(8) -0.0166(7) 0.0056(6) -0.0044(6) C5 0.0352(7) 0.0449(8) 0.0279(7) -0.0124(6) 0.0023(6) 0.0011(7) C6 0.0357(7) 0.0354(7) 0.0257(7) -0.0060(6) 0.0071(6) 0.0023(6) C7 0.0289(6) 0.0267(7) 0.0257(6) -0.0060(5) 0.0063(5) 0.0017(5) C8 0.0266(6) 0.0266(6) 0.0221(6) -0.0040(5) 0.0071(5) 0.0020(5) C9 0.0240(6) 0.0287(7) 0.0211(6) -0.0021(5) 0.0072(5) 0.0009(5) C10 0.0244(6) 0.0274(7) 0.0239(6) -0.0019(5) 0.0069(5) -0.0020(5) C11 0.0373(7) 0.0357(7) 0.0242(6) -0.0011(6) 0.0103(6) -0.0061(6) C12 0.0482(8) 0.0322(8) 0.0325(7) 0.0044(6) 0.0138(7) -0.0062(7) C13 0.0407(8) 0.0268(7) 0.0377(8) -0.0011(6) 0.0144(6) -0.0043(6) C14 0.0297(7) 0.0287(7) 0.0294(7) -0.0054(5) 0.0100(5) -0.0020(5) C15 0.0230(6) 0.0274(7) 0.0242(6) -0.0019(5) 0.0066(5) -0.0007(5) C16 0.0207(6) 0.0262(6) 0.0202(6) -0.0035(5) 0.0029(5) -0.0001(5) C17 0.0232(6) 0.0275(7) 0.0180(6) -0.0008(5) 0.0021(5) 0.0023(5) C18 0.0263(6) 0.0325(7) 0.0197(6) 0.0033(5) 0.0047(5) 0.0026(5) C19 0.0316(7) 0.0356(7) 0.0227(6) 0.0005(5) 0.0077(5) 0.0033(6) C20 0.0409(8) 0.0444(8) 0.0301(7) -0.0004(6) 0.0173(6) 0.0021(7) C21 0.0433(8) 0.0505(9) 0.0386(8) 0.0031(7) 0.0233(7) -0.0031(7) C22 0.0387(8) 0.0389(8) 0.0346(7) 0.0030(6) 0.0149(6) -0.0055(6) C23 0.0305(7) 0.0325(7) 0.0236(6) 0.0033(5) 0.0075(5) 0.0003(6) C24 0.0288(6) 0.0273(7) 0.0245(6) 0.0034(5) 0.0065(5) -0.0004(5) C25 0.0242(6) 0.0277(6) 0.0220(6) 0.0000(5) 0.0055(5) 0.0051(5) C26 0.0271(6) 0.0299(7) 0.0256(6) 0.0067(5) 0.0091(5) 0.0016(5) C27 0.0263(6) 0.0259(6) 0.0286(7) 0.0024(5) 0.0070(5) -0.0018(5) C28 0.0273(6) 0.0287(7) 0.0224(6) 0.0015(5) 0.0053(5) 0.0024(5) C29 0.0380(7) 0.0323(7) 0.0289(7) 0.0094(6) 0.0066(6) -0.0042(6) C30 0.0331(7) 0.0279(7) 0.0313(7) 0.0039(6) 0.0036(6) -0.0046(6) B1 0.0256(7) 0.0252(7) 0.0213(7) -0.0015(6) 0.0051(6) 0.0005(6) C1S 0.0305(7) 0.0526(9) 0.0314(7) 0.0045(7) 0.0016(6) 0.0102(7) C2S 0.0381(8) 0.0586(11) 0.0419(9) 0.0133(8) 0.0078(7) 0.0075(8) C3S 0.0499(10) 0.0489(10) 0.0599(12) -0.0023(9) -0.0125(9) 0.0137(8) C4S 0.0551(11) 0.1008(18) 0.0328(9) -0.0094(10) -0.0041(8) 0.0454(12) C5S 0.0420(9) 0.1071(18) 0.0394(10) 0.0131(11) 0.0133(8) 0.0239(11) C6S 0.0326(8) 0.0675(11) 0.0441(9) 0.0150(8) 0.0055(7) 0.0033(8) C7S 0.0635(12) 0.0783(14) 0.0436(10) -0.0116(9) 0.0008(9) 0.0220(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 O1 C25 1.3925(14) . ? O1 B1 1.4348(17) . ? O2 C28 1.3747(15) . ? O2 H1O 0.93(2) . ? N1 C8 1.3631(16) . ? N1 C1 1.3654(17) . ? N1 B1 1.4958(17) . ? N2 C9 1.3416(16) . ? N2 C8 1.3462(17) . ? N3 C16 1.3636(16) . ? N3 C9 1.3698(15) . ? N3 B1 1.5037(18) . ? N4 C16 1.3456(16) . ? N4 C17 1.3484(17) . ? N5 C17 1.3607(16) . ? N5 C24 1.3633(17) . ? N5 B1 1.4930(18) . ? N6 C1 1.3454(17) . ? N6 C24 1.3470(17) . ? C1 C2 1.4581(18) . ? C2 C3 1.3948(19) . ? C2 C7 1.4197(19) . ? C3 C4 1.384(2) . ? C3 H3A 0.9500 . ? C4 C5 1.395(2) . ? C4 H4A 0.9500 . ? C5 C6 1.381(2) . ? C5 H5A 0.9500 . ? C6 C7 1.3963(18) . ? C6 H6A 0.9500 . ? C7 C8 1.4503(18) . ? C9 C10 1.4546(18) . ? C10 C11 1.3884(18) . ? C10 C15 1.4207(17) . ? C11 C12 1.385(2) . ? C11 H11A 0.9500 . ? C12 C13 1.399(2) . ? C12 H12A 0.9500 . ? C13 C14 1.3822(19) . ? C13 H13A 0.9500 . ? C14 C15 1.3938(19) . ? C14 H14A 0.9500 . ? C15 C16 1.4533(18) . ? C17 C18 1.4534(18) . ? C18 C19 1.3897(18) . ? C18 C23 1.4253(19) . ? C19 C20 1.380(2) . ? C19 H19A 0.9500 . ? C20 C21 1.399(2) . ? C20 H20A 0.9500 . ? C21 C22 1.379(2) . ? C21 H21A 0.9500 . ? C22 C23 1.3888(19) . ? C22 H22A 0.9500 . ? C23 C24 1.4532(18) . ? C25 C30 1.3796(18) . ? C25 C26 1.3846(18) . ? C26 C27 1.3867(18) . ? C26 H26A 0.9500 . ? C27 C28 1.3820(18) . ? C27 H27A 0.9500 . ? C28 C29 1.3865(19) . ? C29 C30 1.3894(19) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C1S C6S 1.382(2) . ? C1S C2S 1.383(2) . ? C1S C7S 1.502(2) . ? C2S C3S 1.387(3) . ? C2S H2SA 0.9500 . ? C3S C4S 1.379(3) . ? C3S H3SA 0.9500 . ? C4S C5S 1.369(3) . ? C4S H4SA 0.9500 . ? C5S C6S 1.362(3) . ? C5S H5SA 0.9500 . ? C6S H6SA 0.9500 . ? C7S H7SA 0.9800 . ? C7S H7SB 0.9800 . ? C7S H7SC 0.9800 . ? 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 117.14(9) . . ? C28 O2 H1O 108.9(11) . . ? C8 N1 C1 113.10(10) . . ? C8 N1 B1 123.19(11) . . ? C1 N1 B1 122.05(11) . . ? C9 N2 C8 117.02(10) . . ? C16 N3 C9 112.17(10) . . ? C16 N3 B1 123.37(10) . . ? C9 N3 B1 123.23(10) . . ? C16 N4 C17 117.31(10) . . ? C17 N5 C24 113.64(11) . . ? C17 N5 B1 123.52(11) . . ? C24 N5 B1 122.50(11) . . ? C1 N6 C24 116.97(11) . . ? N6 C1 N1 122.95(11) . . ? N6 C1 C2 129.62(12) . . ? N1 C1 C2 105.53(11) . . ? C3 C2 C7 120.18(12) . . ? C3 C2 C1 132.59(13) . . ? C7 C2 C1 107.00(11) . . ? C4 C3 C2 118.05(14) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 121.64(13) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 C4 121.27(13) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C7 117.96(13) . . ? C5 C6 H6A 121.0 . . ? C7 C6 H6A 121.0 . . ? C6 C7 C2 120.88(12) . . ? C6 C7 C8 131.58(13) . . ? C2 C7 C8 107.27(11) . . ? N2 C8 N1 123.23(11) . . ? N2 C8 C7 129.19(11) . . ? N1 C8 C7 105.83(11) . . ? N2 C9 N3 122.30(11) . . ? N2 C9 C10 129.83(11) . . ? N3 C9 C10 105.95(10) . . ? C11 C10 C15 120.91(12) . . ? C11 C10 C9 131.96(12) . . ? C15 C10 C9 106.98(11) . . ? C12 C11 C10 117.73(12) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C13 121.59(13) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C14 C13 C12 121.27(13) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C15 117.98(12) . . ? C13 C14 H14A 121.0 . . ? C15 C14 H14A 121.0 . . ? C14 C15 C10 120.50(12) . . ? C14 C15 C16 132.46(12) . . ? C10 C15 C16 106.90(11) . . ? N4 C16 N3 122.12(11) . . ? N4 C16 C15 130.20(11) . . ? N3 C16 C15 106.33(10) . . ? N4 C17 N5 121.94(11) . . ? N4 C17 C18 131.07(11) . . ? N5 C17 C18 105.70(11) . . ? C19 C18 C23 120.95(12) . . ? C19 C18 C17 132.14(12) . . ? C23 C18 C17 106.80(11) . . ? C20 C19 C18 117.71(13) . . ? C20 C19 H19A 121.1 . . ? C18 C19 H19A 121.1 . . ? C19 C20 C21 121.41(13) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.58(13) . . ? C22 C21 H21A 119.2 . . ? C20 C21 H21A 119.2 . . ? C21 C22 C23 118.03(14) . . ? C21 C22 H22A 121.0 . . ? C23 C22 H22A 121.0 . . ? C22 C23 C18 120.31(12) . . ? C22 C23 C24 132.14(13) . . ? C18 C23 C24 107.40(11) . . ? N6 C24 N5 121.97(11) . . ? N6 C24 C23 131.17(12) . . ? N5 C24 C23 105.27(11) . . ? C30 C25 C26 119.53(11) . . ? C30 C25 O1 119.67(11) . . ? C26 C25 O1 120.80(11) . . ? C25 C26 C27 120.35(12) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C28 C27 C26 120.18(12) . . ? C28 C27 H27A 119.9 . . ? C26 C27 H27A 119.9 . . ? O2 C28 C27 117.55(12) . . ? O2 C28 C29 122.92(11) . . ? C27 C28 C29 119.53(12) . . ? C28 C29 C30 120.14(12) . . ? C28 C29 H29A 119.9 . . ? C30 C29 H29A 119.9 . . ? C25 C30 C29 120.27(12) . . ? C25 C30 H30A 119.9 . . ? C29 C30 H30A 119.9 . . ? O1 B1 N5 114.61(10) . . ? O1 B1 N1 112.18(11) . . ? N5 B1 N1 103.91(10) . . ? O1 B1 N3 117.72(11) . . ? N5 B1 N3 103.00(10) . . ? N1 B1 N3 103.89(10) . . ? C6S C1S C2S 118.16(16) . . ? C6S C1S C7S 120.48(17) . . ? C2S C1S C7S 121.35(16) . . ? C1S C2S C3S 120.62(17) . . ? C1S C2S H2SA 119.7 . . ? C3S C2S H2SA 119.7 . . ? C4S C3S C2S 119.86(19) . . ? C4S C3S H3SA 120.1 . . ? C2S C3S H3SA 120.1 . . ? C5S C4S C3S 119.40(18) . . ? C5S C4S H4SA 120.3 . . ? C3S C4S H4SA 120.3 . . ? C6S C5S C4S 120.74(18) . . ? C6S C5S H5SA 119.6 . . ? C4S C5S H5SA 119.6 . . ? C5S C6S C1S 121.22(19) . . ? C5S C6S H6SA 119.4 . . ? C1S C6S H6SA 119.4 . . ? C1S C7S H7SA 109.5 . . ? C1S C7S H7SB 109.5 . . ? H7SA C7S H7SB 109.5 . . ? C1S C7S H7SC 109.5 . . ? H7SA C7S H7SC 109.5 . . ? H7SB C7S H7SC 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 N6 C1 N1 9.79(19) . . . . ? C24 N6 C1 C2 -152.17(13) . . . . ? C8 N1 C1 N6 -154.04(12) . . . . ? B1 N1 C1 N6 11.69(19) . . . . ? C8 N1 C1 C2 11.62(14) . . . . ? B1 N1 C1 C2 177.35(11) . . . . ? N6 C1 C2 C3 -17.0(2) . . . . ? N1 C1 C2 C3 178.69(14) . . . . ? N6 C1 C2 C7 157.38(13) . . . . ? N1 C1 C2 C7 -6.97(14) . . . . ? C7 C2 C3 C4 0.2(2) . . . . ? C1 C2 C3 C4 173.97(14) . . . . ? C2 C3 C4 C5 -1.3(2) . . . . ? C3 C4 C5 C6 1.2(2) . . . . ? C4 C5 C6 C7 0.1(2) . . . . ? C5 C6 C7 C2 -1.1(2) . . . . ? C5 C6 C7 C8 -174.31(13) . . . . ? C3 C2 C7 C6 1.0(2) . . . . ? C1 C2 C7 C6 -174.20(12) . . . . ? C3 C2 C7 C8 175.65(12) . . . . ? C1 C2 C7 C8 0.47(14) . . . . ? C9 N2 C8 N1 -7.93(17) . . . . ? C9 N2 C8 C7 154.78(13) . . . . ? C1 N1 C8 N2 154.79(12) . . . . ? B1 N1 C8 N2 -10.76(18) . . . . ? C1 N1 C8 C7 -11.36(14) . . . . ? B1 N1 C8 C7 -176.90(11) . . . . ? C6 C7 C8 N2 15.1(2) . . . . ? C2 C7 C8 N2 -158.80(12) . . . . ? C6 C7 C8 N1 -179.89(13) . . . . ? C2 C7 C8 N1 6.22(14) . . . . ? C8 N2 C9 N3 5.59(17) . . . . ? C8 N2 C9 C10 -156.33(13) . . . . ? C16 N3 C9 N2 -152.32(11) . . . . ? B1 N3 C9 N2 15.39(18) . . . . ? C16 N3 C9 C10 13.33(13) . . . . ? B1 N3 C9 C10 -178.96(11) . . . . ? N2 C9 C10 C11 -19.8(2) . . . . ? N3 C9 C10 C11 176.00(13) . . . . ? N2 C9 C10 C15 155.67(13) . . . . ? N3 C9 C10 C15 -8.50(13) . . . . ? C15 C10 C11 C12 0.3(2) . . . . ? C9 C10 C11 C12 175.26(14) . . . . ? C10 C11 C12 C13 -1.0(2) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 C15 1.1(2) . . . . ? C13 C14 C15 C10 -1.77(19) . . . . ? C13 C14 C15 C16 -176.87(13) . . . . ? C11 C10 C15 C14 1.11(19) . . . . ? C9 C10 C15 C14 -174.99(11) . . . . ? C11 C10 C15 C16 177.33(12) . . . . ? C9 C10 C15 C16 1.24(13) . . . . ? C17 N4 C16 N3 -8.84(16) . . . . ? C17 N4 C16 C15 156.02(12) . . . . ? C9 N3 C16 N4 155.41(11) . . . . ? B1 N3 C16 N4 -12.28(17) . . . . ? C9 N3 C16 C15 -12.59(13) . . . . ? B1 N3 C16 C15 179.72(11) . . . . ? C14 C15 C16 N4 15.4(2) . . . . ? C10 C15 C16 N4 -160.14(12) . . . . ? C14 C15 C16 N3 -177.89(13) . . . . ? C10 C15 C16 N3 6.53(13) . . . . ? C16 N4 C17 N5 7.02(17) . . . . ? C16 N4 C17 C18 -158.09(12) . . . . ? C24 N5 C17 N4 -157.25(11) . . . . ? B1 N5 C17 N4 16.24(18) . . . . ? C24 N5 C17 C18 11.14(13) . . . . ? B1 N5 C17 C18 -175.37(11) . . . . ? N4 C17 C18 C19 -15.4(2) . . . . ? N5 C17 C18 C19 177.74(13) . . . . ? N4 C17 C18 C23 160.60(12) . . . . ? N5 C17 C18 C23 -6.31(13) . . . . ? C23 C18 C19 C20 0.74(19) . . . . ? C17 C18 C19 C20 176.21(13) . . . . ? C18 C19 C20 C21 -1.0(2) . . . . ? C19 C20 C21 C22 0.3(2) . . . . ? C20 C21 C22 C23 0.8(2) . . . . ? C21 C22 C23 C18 -1.1(2) . . . . ? C21 C22 C23 C24 -176.06(14) . . . . ? C19 C18 C23 C22 0.32(19) . . . . ? C17 C18 C23 C22 -176.18(12) . . . . ? C19 C18 C23 C24 176.43(11) . . . . ? C17 C18 C23 C24 -0.07(14) . . . . ? C1 N6 C24 N5 -6.92(18) . . . . ? C1 N6 C24 C23 156.45(13) . . . . ? C17 N5 C24 N6 155.96(12) . . . . ? B1 N5 C24 N6 -17.61(18) . . . . ? C17 N5 C24 C23 -11.14(14) . . . . ? B1 N5 C24 C23 175.30(11) . . . . ? C22 C23 C24 N6 16.4(2) . . . . ? C18 C23 C24 N6 -159.03(13) . . . . ? C22 C23 C24 N5 -178.13(14) . . . . ? C18 C23 C24 N5 6.39(14) . . . . ? B1 O1 C25 C30 104.67(14) . . . . ? B1 O1 C25 C26 -75.88(15) . . . . ? C30 C25 C26 C27 -0.25(19) . . . . ? O1 C25 C26 C27 -179.70(11) . . . . ? C25 C26 C27 C28 0.34(19) . . . . ? C26 C27 C28 O2 179.32(12) . . . . ? C26 C27 C28 C29 -0.2(2) . . . . ? O2 C28 C29 C30 -179.52(13) . . . . ? C27 C28 C29 C30 0.0(2) . . . . ? C26 C25 C30 C29 0.0(2) . . . . ? O1 C25 C30 C29 179.47(12) . . . . ? C28 C29 C30 C25 0.1(2) . . . . ? C25 O1 B1 N5 -41.66(15) . . . . ? C25 O1 B1 N1 -159.84(10) . . . . ? C25 O1 B1 N3 79.69(14) . . . . ? C17 N5 B1 O1 97.72(14) . . . . ? C24 N5 B1 O1 -89.35(14) . . . . ? C17 N5 B1 N1 -139.51(11) . . . . ? C24 N5 B1 N1 33.41(15) . . . . ? C17 N5 B1 N3 -31.40(15) . . . . ? C24 N5 B1 N3 141.53(11) . . . . ? C8 N1 B1 O1 -101.74(13) . . . . ? C1 N1 B1 O1 93.98(14) . . . . ? C8 N1 B1 N5 133.90(12) . . . . ? C1 N1 B1 N5 -30.37(15) . . . . ? C8 N1 B1 N3 26.45(15) . . . . ? C1 N1 B1 N3 -137.83(11) . . . . ? C16 N3 B1 O1 -97.72(14) . . . . ? C9 N3 B1 O1 95.93(14) . . . . ? C16 N3 B1 N5 29.45(15) . . . . ? C9 N3 B1 N5 -136.90(11) . . . . ? C16 N3 B1 N1 137.59(11) . . . . ? C9 N3 B1 N1 -28.77(15) . . . . ? C6S C1S C2S C3S 0.1(2) . . . . ? C7S C1S C2S C3S -179.58(15) . . . . ? C1S C2S C3S C4S -0.3(2) . . . . ? C2S C3S C4S C5S 0.0(2) . . . . ? C3S C4S C5S C6S 0.5(3) . . . . ? C4S C5S C6S C1S -0.7(2) . . . . ? C2S C1S C6S C5S 0.4(2) . . . . ? C7S C1S C6S C5S -179.93(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1O N4 0.93(2) 1.87(2) 2.7993(14) 175.4(17) 2_645 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.214 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.040 _iucr_refine_instructions_details ; TITL cu_d12137_0m in P2(1)/c CELL 1.54178 16.2110 9.4838 20.4044 90.000 110.991 90.000 ZERR 4.00 0.0011 0.0006 0.0014 0.000 0.004 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N O B UNIT 148 100 24 8 4 TEMP -126.160 SIZE 0.12, 0.10, 0.05 ACTA L.S. 4 FMAP 2 PLAN 20 EQIV $1 -x+1, y-1/2, -z+1/2 HTAB O2 N4_$1 BOND $H CONF WGHT 0.0404 0.9463 FVAR 0.13933 O1 4 0.423271 0.426877 0.046696 11.00000 0.02983 0.02847 = 0.02188 -0.00265 0.00369 0.00504 O2 4 0.639573 0.517126 0.323676 11.00000 0.04191 0.03294 = 0.02298 0.00397 0.00092 -0.00416 N1 3 0.278721 0.450803 -0.045366 11.00000 0.02723 0.02432 = 0.02158 -0.00214 0.00558 0.00032 N2 3 0.304314 0.609857 -0.126509 11.00000 0.02824 0.02817 = 0.02217 -0.00433 0.00826 -0.00036 N3 3 0.358832 0.660962 -0.004473 11.00000 0.02376 0.02528 = 0.01965 -0.00244 0.00588 -0.00033 N4 3 0.345754 0.774282 0.094916 11.00000 0.02299 0.02767 = 0.01887 -0.00146 0.00357 0.00035 N5 3 0.297261 0.538789 0.066903 11.00000 0.02636 0.02617 = 0.02012 -0.00005 0.00544 -0.00046 N6 3 0.190535 0.360979 0.016726 11.00000 0.03379 0.02719 = 0.02716 -0.00092 0.00854 -0.00314 C1 1 0.210872 0.370074 -0.041540 11.00000 0.02913 0.02329 = 0.02781 -0.00129 0.00730 -0.00139 C2 1 0.157823 0.334258 -0.113914 11.00000 0.02967 0.02616 = 0.02892 -0.00649 0.00732 0.00057 C3 1 0.081744 0.253010 -0.143554 11.00000 0.03137 0.03372 = 0.03861 -0.00967 0.01046 -0.00394 AFIX 43 H3A 2 0.057692 0.200874 -0.114872 11.00000 -1.20000 AFIX 0 C4 1 0.042321 0.250578 -0.215988 11.00000 0.02918 0.04338 = 0.04026 -0.01658 0.00562 -0.00441 AFIX 43 H4A 2 -0.008819 0.194239 -0.237103 11.00000 -1.20000 AFIX 0 C5 1 0.075831 0.328802 -0.258730 11.00000 0.03525 0.04485 = 0.02792 -0.01229 0.00236 0.00108 AFIX 43 H5A 2 0.046425 0.326043 -0.308212 11.00000 -1.20000 AFIX 0 C6 1 0.150912 0.410165 -0.230517 11.00000 0.03570 0.03548 = 0.02577 -0.00595 0.00714 0.00235 AFIX 43 H6A 2 0.173505 0.463341 -0.259807 11.00000 -1.20000 AFIX 0 C7 1 0.192618 0.411895 -0.157611 11.00000 0.02898 0.02679 = 0.02573 -0.00596 0.00630 0.00167 C8 1 0.266714 0.493232 -0.111974 11.00000 0.02662 0.02665 = 0.02222 -0.00399 0.00708 0.00197 C9 1 0.346833 0.695153 -0.072499 11.00000 0.02399 0.02872 = 0.02107 -0.00215 0.00714 0.00086 C10 1 0.366829 0.844754 -0.072106 11.00000 0.02451 0.02746 = 0.02392 -0.00185 0.00689 -0.00197 C11 1 0.370710 0.935028 -0.124484 11.00000 0.03733 0.03577 = 0.02423 -0.00110 0.01034 -0.00609 AFIX 43 H11A 2 0.363456 0.900750 -0.169964 11.00000 -1.20000 AFIX 0 C12 1 0.385516 1.076751 -0.108170 11.00000 0.04820 0.03231 = 0.03257 0.00435 0.01379 -0.00625 AFIX 43 H12A 2 0.389345 1.140267 -0.142970 11.00000 -1.20000 AFIX 0 C13 1 0.394969 1.128637 -0.041713 11.00000 0.04080 0.02687 = 0.03772 -0.00109 0.01445 -0.00429 AFIX 43 H13A 2 0.404810 1.226569 -0.032389 11.00000 -1.20000 AFIX 0 C14 1 0.390268 1.040143 0.010680 11.00000 0.02976 0.02870 = 0.02945 -0.00537 0.01002 -0.00200 AFIX 43 H14A 2 0.395691 1.076033 0.055504 11.00000 -1.20000 AFIX 0 C15 1 0.377329 0.896652 -0.004271 11.00000 0.02306 0.02740 = 0.02428 -0.00189 0.00665 -0.00067 C16 1 0.365562 0.777467 0.036290 11.00000 0.02081 0.02621 = 0.02015 -0.00354 0.00284 -0.00006 C17 1 0.307297 0.656282 0.107312 11.00000 0.02325 0.02752 = 0.01803 -0.00077 0.00215 0.00236 C18 1 0.253836 0.632535 0.150228 11.00000 0.02633 0.03262 = 0.01978 0.00327 0.00474 0.00253 C19 1 0.240184 0.712603 0.202483 11.00000 0.03173 0.03559 = 0.02276 0.00046 0.00771 0.00332 AFIX 43 H19A 2 0.271121 0.798488 0.218186 11.00000 -1.20000 AFIX 0 C20 1 0.180110 0.663011 0.230778 11.00000 0.04102 0.04441 = 0.03015 -0.00040 0.01732 0.00218 AFIX 43 H20A 2 0.170341 0.715048 0.267116 11.00000 -1.20000 AFIX 0 C21 1 0.133295 0.537746 0.207089 11.00000 0.04331 0.05058 = 0.03863 0.00309 0.02329 -0.00304 AFIX 43 H21A 2 0.092250 0.506905 0.227583 11.00000 -1.20000 AFIX 0 C22 1 0.145312 0.458010 0.154716 11.00000 0.03874 0.03894 = 0.03463 0.00303 0.01489 -0.00542 AFIX 43 H22A 2 0.112697 0.373708 0.138567 11.00000 -1.20000 AFIX 0 C23 1 0.206517 0.504589 0.126265 11.00000 0.03049 0.03256 = 0.02368 0.00328 0.00758 0.00030 C24 1 0.231380 0.451747 0.069087 11.00000 0.02876 0.02742 = 0.02457 0.00339 0.00656 -0.00043 C25 1 0.476904 0.449449 0.116404 11.00000 0.02425 0.02778 = 0.02201 0.00002 0.00554 0.00514 C26 1 0.533127 0.564438 0.135195 11.00000 0.02717 0.03004 = 0.02569 0.00665 0.00909 0.00162 AFIX 43 H26A 2 0.535099 0.629197 0.100265 11.00000 -1.20000 AFIX 0 C27 1 0.586578 0.585614 0.204716 11.00000 0.02639 0.02598 = 0.02868 0.00248 0.00706 -0.00184 AFIX 43 H27A 2 0.624774 0.665021 0.217270 11.00000 -1.20000 AFIX 0 C28 1 0.584426 0.491476 0.255799 11.00000 0.02743 0.02877 = 0.02244 0.00144 0.00533 0.00246 C29 1 0.528278 0.376108 0.237038 11.00000 0.03809 0.03229 = 0.02896 0.00935 0.00670 -0.00419 AFIX 43 H29A 2 0.526505 0.311010 0.271896 11.00000 -1.20000 AFIX 0 C30 1 0.474595 0.355526 0.167349 11.00000 0.03318 0.02795 = 0.03138 0.00389 0.00366 -0.00457 AFIX 43 H30A 2 0.436138 0.276440 0.154731 11.00000 -1.20000 AFIX 0 B1 5 0.346383 0.514307 0.018447 11.00000 0.02561 0.02529 = 0.02139 -0.00156 0.00514 0.00048 C1S 1 0.115796 0.900809 0.024361 11.00000 0.03052 0.05266 = 0.03150 0.00456 0.00158 0.01017 C2S 1 0.079761 0.766965 0.017753 11.00000 0.03812 0.05871 = 0.04194 0.01330 0.00781 0.00751 AFIX 43 H2SA 2 0.055672 0.734481 0.051153 11.00000 -1.20000 AFIX 0 C3S 1 0.078475 0.679774 -0.037175 11.00000 0.04989 0.04895 = 0.05998 -0.00235 -0.01248 0.01377 AFIX 43 H3SA 2 0.053857 0.587854 -0.041191 11.00000 -1.20000 AFIX 0 C4S 1 0.113004 0.726786 -0.085943 11.00000 0.05510 0.10112 = 0.03276 -0.00928 -0.00405 0.04551 AFIX 43 H4SA 2 0.112308 0.667622 -0.123707 11.00000 -1.20000 AFIX 0 C5S 1 0.148289 0.859451 -0.079459 11.00000 0.04206 0.10713 = 0.03940 0.01306 0.01335 0.02385 AFIX 43 H5SA 2 0.171759 0.892426 -0.113149 11.00000 -1.20000 AFIX 0 C6S 1 0.150124 0.944727 -0.025224 11.00000 0.03263 0.06756 = 0.04409 0.01502 0.00551 0.00327 AFIX 43 H6SA 2 0.175470 1.036075 -0.021418 11.00000 -1.20000 AFIX 0 C7S 1 0.118311 0.996339 0.083776 11.00000 0.06348 0.07839 = 0.04369 -0.01167 0.00085 0.02209 AFIX 137 H7SA 2 0.088513 0.950439 0.112216 11.00000 -1.50000 H7SB 2 0.088176 1.085026 0.064810 11.00000 -1.50000 H7SC 2 0.179885 1.015871 0.113062 11.00000 -1.50000 AFIX 0 H1O 2 0.641371 0.437242 0.350672 11.00000 0.05502 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_d12137_0m in P2(1)/c REM R1 = 0.0347 for 4510 Fo > 4sig(Fo) and 0.0384 for all 5000 data REM 420 parameters refined using 0 restraints END REM Highest difference peak 0.214, deepest hole -0.223, 1-sigma level 0.040 Q1 1 0.0501 1.0293 0.0834 11.00000 0.05 0.21 Q2 1 0.4590 0.4616 0.0210 11.00000 0.05 0.16 Q3 1 0.3198 0.5289 0.0442 11.00000 0.05 0.16 Q4 1 0.1536 1.1084 0.0695 11.00000 0.05 0.16 Q5 1 -0.0262 0.1189 -0.2337 11.00000 0.05 0.16 Q6 1 0.1652 0.3967 -0.1381 11.00000 0.05 0.15 Q7 1 0.5308 0.4693 0.2473 11.00000 0.05 0.15 Q8 1 0.2368 0.4391 -0.1418 11.00000 0.05 0.15 Q9 1 0.3057 0.4791 -0.0155 11.00000 0.05 0.15 Q10 1 0.1923 0.4585 0.1517 11.00000 0.05 0.14 Q11 1 0.0800 0.2545 -0.2334 11.00000 0.05 0.13 Q12 1 0.1686 0.4384 -0.1896 11.00000 0.05 0.13 Q13 1 0.3909 0.8693 -0.0384 11.00000 0.05 0.12 Q14 1 0.0890 0.6016 -0.1204 11.00000 0.05 0.12 Q15 1 0.5077 0.3453 0.2923 11.00000 0.05 0.12 Q16 1 0.3397 0.8961 -0.1017 11.00000 0.05 0.12 Q17 1 0.5844 0.5485 0.1663 11.00000 0.05 0.12 Q18 1 -0.0047 0.3180 -0.3224 11.00000 0.05 0.12 Q19 1 0.2873 1.0304 -0.2361 11.00000 0.05 0.12 Q20 1 0.2882 0.6394 0.1429 11.00000 0.05 0.11 ; _database_code_depnum_ccdc_archive 'CCDC 949039' ####################################################################### # # 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_d1257 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-Hydroxyphenolato)(subphthalocyaninato)boron ; _chemical_name_common ; m-HOPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H17 B N6 O2, 0.69(C H2 Cl2), 0.31(H2 O)' _chemical_formula_sum 'C30.69 H19 B Cl1.38 N6 O2.31' _chemical_formula_weight 568.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 8.9397(5) _cell_length_b 12.8974(8) _cell_length_c 13.0121(7) _cell_angle_alpha 105.828(3) _cell_angle_beta 109.874(3) _cell_angle_gamma 99.661(3) _cell_volume 1299.93(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9953 _cell_measurement_theta_min 6.34 _cell_measurement_theta_max 65.68 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584.8 _exptl_absorpt_coefficient_mu 2.021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6110 _exptl_absorpt_correction_T_max 0.7527 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source I\mS _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_measurement_device_type 'Bruker APEX-DUO' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14212 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.49 _diffrn_reflns_theta_max 66.13 _reflns_number_total 4276 _reflns_number_gt 4025 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0000P)^2^+4.1045P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4276 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1743 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 O1 O 0.5810(3) 0.7286(2) 0.6249(2) 0.0336(7) Uani 1 1 d . . . O2 O 0.5930(4) 0.6854(3) 0.2539(3) 0.0404(7) Uani 1 1 d . . . H2O H 0.612(7) 0.622(5) 0.258(5) 0.061 Uiso 1 1 d . . . N1 N 0.3515(4) 0.6853(3) 0.6887(3) 0.0294(7) Uani 1 1 d . . . N2 N 0.4246(4) 0.5349(3) 0.7466(3) 0.0313(8) Uani 1 1 d . . . N3 N 0.6301(4) 0.7070(3) 0.8077(3) 0.0305(7) Uani 1 1 d . . . N4 N 0.8006(4) 0.8890(3) 0.9408(3) 0.0344(8) Uani 1 1 d . . . N5 N 0.5430(4) 0.8656(3) 0.7881(3) 0.0296(7) Uani 1 1 d . . . N6 N 0.2539(4) 0.8476(3) 0.7172(3) 0.0305(7) Uani 1 1 d . . . C1 C 0.2259(5) 0.7349(3) 0.6801(3) 0.0288(8) Uani 1 1 d . . . C2 C 0.0802(5) 0.6461(3) 0.6550(3) 0.0307(9) Uani 1 1 d . . . C3 C -0.0811(5) 0.6470(4) 0.6402(3) 0.0346(9) Uani 1 1 d . . . H3A H -0.1153 0.7129 0.6407 0.042 Uiso 1 1 calc R . . C4 C -0.1906(5) 0.5478(4) 0.6248(4) 0.0375(10) Uani 1 1 d . . . H4A H -0.3027 0.5454 0.6114 0.045 Uiso 1 1 calc R . . C5 C -0.1399(5) 0.4518(4) 0.6285(4) 0.0375(10) Uani 1 1 d . . . H5A H -0.2179 0.3856 0.6176 0.045 Uiso 1 1 calc R . . C6 C 0.0224(5) 0.4512(3) 0.6479(3) 0.0345(9) Uani 1 1 d . . . H6A H 0.0573 0.3864 0.6522 0.041 Uiso 1 1 calc R . . C7 C 0.1320(5) 0.5488(3) 0.6607(3) 0.0301(9) Uani 1 1 d . . . C8 C 0.3105(5) 0.5797(3) 0.6929(3) 0.0291(8) Uani 1 1 d . . . C9 C 0.5813(5) 0.6014(3) 0.8107(3) 0.0305(9) Uani 1 1 d . . . C10 C 0.7142(5) 0.5961(3) 0.9097(3) 0.0314(9) Uani 1 1 d . . . C11 C 0.7340(6) 0.5118(4) 0.9577(4) 0.0410(10) Uani 1 1 d . . . H11A H 0.6554 0.4394 0.9205 0.049 Uiso 1 1 calc R . . C12 C 0.8706(6) 0.5368(4) 1.0604(4) 0.0454(11) Uani 1 1 d . . . H12A H 0.8882 0.4800 1.0929 0.054 Uiso 1 1 calc R . . C13 C 0.9837(6) 0.6444(4) 1.1172(4) 0.0449(11) Uani 1 1 d . . . H13A H 1.0763 0.6591 1.1880 0.054 Uiso 1 1 calc R . . C14 C 0.9648(5) 0.7299(4) 1.0738(4) 0.0385(10) Uani 1 1 d . . . H14A H 1.0411 0.8031 1.1141 0.046 Uiso 1 1 calc R . . C15 C 0.8285(5) 0.7048(4) 0.9676(4) 0.0337(9) Uani 1 1 d . . . C16 C 0.7660(5) 0.7761(3) 0.9050(3) 0.0314(9) Uani 1 1 d . . . C17 C 0.6832(5) 0.9314(3) 0.8867(3) 0.0312(9) Uani 1 1 d . . . C18 C 0.6518(5) 1.0377(3) 0.9281(4) 0.0325(9) Uani 1 1 d . . . C19 C 0.7511(6) 1.1383(4) 1.0193(4) 0.0381(10) Uani 1 1 d . . . H19A H 0.8628 1.1464 1.0672 0.046 Uiso 1 1 calc R . . C20 C 0.6821(6) 1.2261(4) 1.0379(4) 0.0410(11) Uani 1 1 d . . . H20A H 0.7495 1.2965 1.0975 0.049 Uiso 1 1 calc R . . C21 C 0.5165(6) 1.2144(4) 0.9720(4) 0.0388(10) Uani 1 1 d . . . H21A H 0.4736 1.2768 0.9874 0.047 Uiso 1 1 calc R . . C22 C 0.4125(6) 1.1127(3) 0.8836(4) 0.0349(9) Uani 1 1 d . . . H22A H 0.2982 1.1033 0.8409 0.042 Uiso 1 1 calc R . . C23 C 0.4832(5) 1.0259(3) 0.8611(3) 0.0318(9) Uani 1 1 d . . . C24 C 0.4121(5) 0.9105(3) 0.7769(3) 0.0300(9) Uani 1 1 d . . . C25 C 0.5317(5) 0.7582(3) 0.5280(3) 0.0298(9) Uani 1 1 d . . . C26 C 0.5822(5) 0.7071(3) 0.4415(3) 0.0294(8) Uani 1 1 d . . . H26A H 0.6440 0.6547 0.4519 0.035 Uiso 1 1 calc R . . C27 C 0.5421(5) 0.7328(3) 0.3392(3) 0.0319(9) Uani 1 1 d . . . C28 C 0.4504(6) 0.8073(4) 0.3234(4) 0.0411(10) Uani 1 1 d . . . H28A H 0.4215 0.8242 0.2537 0.049 Uiso 1 1 calc R . . C29 C 0.4007(6) 0.8575(4) 0.4095(4) 0.0413(10) Uani 1 1 d . . . H29A H 0.3384 0.9094 0.3987 0.050 Uiso 1 1 calc R . . C30 C 0.4405(6) 0.8330(4) 0.5119(4) 0.0367(10) Uani 1 1 d . . . H30A H 0.4050 0.8678 0.5702 0.044 Uiso 1 1 calc R . . B1 B 0.5270(6) 0.7474(4) 0.7181(4) 0.0304(10) Uani 1 1 d . . . Cl1 Cl 0.9155(2) 0.96689(13) 0.75126(14) 0.0424(6) Uani 0.690(5) 1 d P A 1 Cl2 Cl 1.0277(2) 1.10671(15) 0.63566(19) 0.0451(6) Uani 0.690(5) 1 d P A 1 C1S C 0.9372(8) 0.9678(5) 0.6225(5) 0.0335(14) Uani 0.690(5) 1 d P A 1 H1SA H 0.8268 0.9362 0.5560 0.040 Uiso 0.690(5) 1 calc PR A 1 H1SB H 1.0080 0.9197 0.6063 0.040 Uiso 0.690(5) 1 calc PR A 1 O1W O 1.024(3) 1.1066(19) 0.573(2) 0.129(8) Uani 0.310(5) 1 d P A 2 H1WA H 0.9387 1.0628 0.5677 0.193 Uiso 0.310(5) 1 d PR A 2 H1WB H 1.0472 1.1375 0.5293 0.193 Uiso 0.310(5) 1 d PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0381(15) 0.0428(16) 0.0271(14) 0.0173(13) 0.0128(12) 0.0219(13) O2 0.059(2) 0.0368(17) 0.0336(16) 0.0146(14) 0.0229(15) 0.0210(15) N1 0.0303(17) 0.0291(17) 0.0246(16) 0.0082(14) 0.0062(14) 0.0108(14) N2 0.0341(18) 0.0280(17) 0.0264(17) 0.0069(14) 0.0071(14) 0.0116(14) N3 0.0301(17) 0.0342(18) 0.0256(17) 0.0102(14) 0.0084(14) 0.0122(14) N4 0.0306(18) 0.039(2) 0.0324(18) 0.0150(16) 0.0106(15) 0.0087(15) N5 0.0302(17) 0.0304(17) 0.0274(17) 0.0107(14) 0.0095(14) 0.0105(14) N6 0.0309(17) 0.0297(18) 0.0296(17) 0.0109(14) 0.0091(14) 0.0114(14) C1 0.032(2) 0.028(2) 0.0250(19) 0.0086(16) 0.0078(16) 0.0139(17) C2 0.034(2) 0.029(2) 0.0245(19) 0.0065(16) 0.0077(16) 0.0107(17) C3 0.033(2) 0.037(2) 0.029(2) 0.0104(18) 0.0062(17) 0.0135(18) C4 0.030(2) 0.040(2) 0.034(2) 0.0087(19) 0.0064(18) 0.0090(18) C5 0.033(2) 0.035(2) 0.031(2) 0.0079(18) 0.0043(18) 0.0036(18) C6 0.038(2) 0.029(2) 0.025(2) 0.0055(17) 0.0032(17) 0.0077(18) C7 0.032(2) 0.030(2) 0.0211(18) 0.0059(16) 0.0039(16) 0.0094(17) C8 0.035(2) 0.0233(19) 0.0261(19) 0.0055(16) 0.0093(16) 0.0121(16) C9 0.035(2) 0.029(2) 0.028(2) 0.0104(17) 0.0112(17) 0.0143(17) C10 0.032(2) 0.033(2) 0.028(2) 0.0109(17) 0.0087(17) 0.0133(17) C11 0.040(2) 0.039(2) 0.039(2) 0.015(2) 0.008(2) 0.013(2) C12 0.047(3) 0.044(3) 0.040(3) 0.021(2) 0.005(2) 0.015(2) C13 0.042(3) 0.051(3) 0.034(2) 0.019(2) 0.003(2) 0.015(2) C14 0.032(2) 0.043(2) 0.036(2) 0.016(2) 0.0066(18) 0.0090(19) C15 0.033(2) 0.043(2) 0.031(2) 0.0174(19) 0.0125(18) 0.0175(19) C16 0.028(2) 0.032(2) 0.031(2) 0.0099(17) 0.0103(17) 0.0080(17) C17 0.031(2) 0.033(2) 0.028(2) 0.0111(17) 0.0109(17) 0.0072(17) C18 0.038(2) 0.032(2) 0.030(2) 0.0132(17) 0.0156(18) 0.0094(18) C19 0.041(2) 0.038(2) 0.030(2) 0.0113(18) 0.0124(19) 0.0041(19) C20 0.053(3) 0.030(2) 0.033(2) 0.0059(18) 0.018(2) 0.003(2) C21 0.056(3) 0.030(2) 0.036(2) 0.0106(19) 0.025(2) 0.015(2) C22 0.041(2) 0.033(2) 0.032(2) 0.0095(18) 0.0169(19) 0.0115(18) C23 0.040(2) 0.028(2) 0.029(2) 0.0093(17) 0.0162(18) 0.0083(17) C24 0.036(2) 0.028(2) 0.028(2) 0.0112(17) 0.0128(17) 0.0128(17) C25 0.031(2) 0.030(2) 0.0243(19) 0.0096(16) 0.0063(16) 0.0083(16) C26 0.032(2) 0.028(2) 0.027(2) 0.0102(16) 0.0093(17) 0.0104(16) C27 0.041(2) 0.025(2) 0.027(2) 0.0068(16) 0.0125(17) 0.0064(17) C28 0.054(3) 0.041(3) 0.035(2) 0.021(2) 0.018(2) 0.021(2) C29 0.050(3) 0.039(2) 0.040(2) 0.020(2) 0.016(2) 0.023(2) C30 0.045(2) 0.037(2) 0.030(2) 0.0108(18) 0.0147(19) 0.019(2) B1 0.033(2) 0.031(2) 0.025(2) 0.0091(19) 0.0089(19) 0.0140(19) Cl1 0.0535(10) 0.0357(9) 0.0440(10) 0.0122(7) 0.0317(8) 0.0057(7) Cl2 0.0585(11) 0.0366(9) 0.0430(11) 0.0161(8) 0.0262(9) 0.0056(7) C1S 0.035(3) 0.028(3) 0.036(3) 0.009(3) 0.016(3) 0.007(2) O1W 0.16(2) 0.109(16) 0.067(13) 0.009(12) 0.023(14) 0.017(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 O1 C25 1.367(5) . ? O1 B1 1.429(5) . ? O2 C27 1.371(5) . ? O2 H2O 0.87(6) . ? N1 C8 1.371(5) . ? N1 C1 1.371(5) . ? N1 B1 1.501(6) . ? N2 C8 1.340(5) . ? N2 C9 1.344(5) . ? N3 C16 1.360(5) . ? N3 C9 1.375(5) . ? N3 B1 1.497(5) . ? N4 C17 1.340(5) . ? N4 C16 1.347(5) . ? N5 C24 1.372(5) . ? N5 C17 1.376(5) . ? N5 B1 1.502(6) . ? N6 C24 1.336(5) . ? N6 C1 1.350(5) . ? C1 C2 1.455(6) . ? C2 C3 1.391(6) . ? C2 C7 1.421(6) . ? C3 C4 1.394(6) . ? C3 H3A 0.9500 . ? C4 C5 1.396(6) . ? C4 H4A 0.9500 . ? C5 C6 1.387(6) . ? C5 H5A 0.9500 . ? C6 C7 1.390(6) . ? C6 H6A 0.9500 . ? C7 C8 1.456(6) . ? C9 C10 1.452(6) . ? C10 C11 1.401(6) . ? C10 C15 1.413(6) . ? C11 C12 1.381(6) . ? C11 H11A 0.9500 . ? C12 C13 1.399(7) . ? C12 H12A 0.9500 . ? C13 C14 1.379(6) . ? C13 H13A 0.9500 . ? C14 C15 1.406(6) . ? C14 H14A 0.9500 . ? C15 C16 1.447(6) . ? C17 C18 1.441(6) . ? C18 C19 1.392(6) . ? C18 C23 1.418(6) . ? C19 C20 1.381(7) . ? C19 H19A 0.9500 . ? C20 C21 1.394(7) . ? C20 H20A 0.9500 . ? C21 C22 1.396(6) . ? C21 H21A 0.9500 . ? C22 C23 1.387(6) . ? C22 H22A 0.9500 . ? C23 C24 1.463(6) . ? C25 C30 1.378(6) . ? C25 C26 1.396(6) . ? C26 C27 1.402(6) . ? C26 H26A 0.9500 . ? C27 C28 1.377(6) . ? C28 C29 1.382(6) . ? C28 H28A 0.9500 . ? C29 C30 1.395(6) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? Cl1 C1S 1.754(6) . ? Cl2 C1S 1.774(6) . ? Cl2 H1WA 0.9133 . ? Cl2 H1WB 1.5944 . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C1S H1WA 1.5774 . ? O1W H1WA 0.8400 . ? O1W H1WB 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 B1 129.5(3) . . ? C27 O2 H2O 111(4) . . ? C8 N1 C1 112.8(3) . . ? C8 N1 B1 122.0(3) . . ? C1 N1 B1 123.9(3) . . ? C8 N2 C9 118.3(3) . . ? C16 N3 C9 112.6(3) . . ? C16 N3 B1 123.3(3) . . ? C9 N3 B1 123.2(3) . . ? C17 N4 C16 117.1(4) . . ? C24 N5 C17 112.2(3) . . ? C24 N5 B1 124.1(3) . . ? C17 N5 B1 122.3(3) . . ? C24 N6 C1 116.9(3) . . ? N6 C1 N1 122.6(4) . . ? N6 C1 C2 129.9(4) . . ? N1 C1 C2 105.7(3) . . ? C3 C2 C7 120.4(4) . . ? C3 C2 C1 131.8(4) . . ? C7 C2 C1 107.5(3) . . ? C2 C3 C4 117.7(4) . . ? C2 C3 H3A 121.2 . . ? C4 C3 H3A 121.2 . . ? C3 C4 C5 121.6(4) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C7 117.8(4) . . ? C5 C6 H6A 121.1 . . ? C7 C6 H6A 121.1 . . ? C6 C7 C2 121.2(4) . . ? C6 C7 C8 131.5(4) . . ? C2 C7 C8 106.9(3) . . ? N2 C8 N1 122.4(4) . . ? N2 C8 C7 129.5(4) . . ? N1 C8 C7 105.8(3) . . ? N2 C9 N3 121.2(3) . . ? N2 C9 C10 131.4(4) . . ? N3 C9 C10 105.9(3) . . ? C11 C10 C15 120.6(4) . . ? C11 C10 C9 132.3(4) . . ? C15 C10 C9 106.7(3) . . ? C12 C11 C10 118.3(4) . . ? C12 C11 H11A 120.9 . . ? C10 C11 H11A 120.9 . . ? C11 C12 C13 120.9(4) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C14 C13 C12 122.0(4) . . ? C14 C13 H13A 119.0 . . ? C12 C13 H13A 119.0 . . ? C13 C14 C15 117.6(4) . . ? C13 C14 H14A 121.2 . . ? C15 C14 H14A 121.2 . . ? C14 C15 C10 120.6(4) . . ? C14 C15 C16 131.2(4) . . ? C10 C15 C16 107.9(3) . . ? N4 C16 N3 122.3(4) . . ? N4 C16 C15 130.2(4) . . ? N3 C16 C15 105.8(3) . . ? N4 C17 N5 122.5(4) . . ? N4 C17 C18 129.9(4) . . ? N5 C17 C18 105.9(3) . . ? C19 C18 C23 120.1(4) . . ? C19 C18 C17 132.0(4) . . ? C23 C18 C17 107.8(4) . . ? C20 C19 C18 117.9(4) . . ? C20 C19 H19A 121.1 . . ? C18 C19 H19A 121.1 . . ? C19 C20 C21 121.9(4) . . ? C19 C20 H20A 119.0 . . ? C21 C20 H20A 119.0 . . ? C20 C21 C22 121.2(4) . . ? C20 C21 H21A 119.4 . . ? C22 C21 H21A 119.4 . . ? C23 C22 C21 117.1(4) . . ? C23 C22 H22A 121.5 . . ? C21 C22 H22A 121.5 . . ? C22 C23 C18 121.7(4) . . ? C22 C23 C24 131.4(4) . . ? C18 C23 C24 106.7(3) . . ? N6 C24 N5 122.6(3) . . ? N6 C24 C23 130.3(4) . . ? N5 C24 C23 105.7(3) . . ? O1 C25 C30 125.3(4) . . ? O1 C25 C26 115.0(3) . . ? C30 C25 C26 119.7(4) . . ? C25 C26 C27 120.2(4) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? O2 C27 C28 118.8(4) . . ? O2 C27 C26 121.3(4) . . ? C28 C27 C26 119.9(4) . . ? C27 C28 C29 119.6(4) . . ? C27 C28 H28A 120.2 . . ? C29 C28 H28A 120.2 . . ? C28 C29 C30 121.1(4) . . ? C28 C29 H29A 119.5 . . ? C30 C29 H29A 119.5 . . ? C25 C30 C29 119.6(4) . . ? C25 C30 H30A 120.2 . . ? C29 C30 H30A 120.2 . . ? O1 B1 N3 108.3(3) . . ? O1 B1 N1 117.0(3) . . ? N3 B1 N1 104.1(3) . . ? O1 B1 N5 119.3(4) . . ? N3 B1 N5 103.4(3) . . ? N1 B1 N5 103.1(3) . . ? C1S Cl2 H1WA 62.6 . . ? C1S Cl2 H1WB 122.9 . . ? H1WA Cl2 H1WB 70.3 . . ? Cl1 C1S Cl2 110.7(3) . . ? Cl1 C1S H1SA 109.5 . . ? Cl2 C1S H1SA 109.5 . . ? Cl1 C1S H1SB 109.5 . . ? Cl2 C1S H1SB 109.5 . . ? H1SA C1S H1SB 108.1 . . ? Cl1 C1S H1WA 130.3 . . ? Cl2 C1S H1WA 30.9 . . ? H1SA C1S H1WA 79.5 . . ? H1SB C1S H1WA 113.6 . . ? H1WA O1W H1WB 134.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 N6 C1 N1 -8.3(6) . . . . ? C24 N6 C1 C2 153.9(4) . . . . ? C8 N1 C1 N6 154.7(4) . . . . ? B1 N1 C1 N6 -11.9(6) . . . . ? C8 N1 C1 C2 -11.2(4) . . . . ? B1 N1 C1 C2 -177.9(3) . . . . ? N6 C1 C2 C3 13.6(7) . . . . ? N1 C1 C2 C3 178.1(4) . . . . ? N6 C1 C2 C7 -159.1(4) . . . . ? N1 C1 C2 C7 5.4(4) . . . . ? C7 C2 C3 C4 -3.6(6) . . . . ? C1 C2 C3 C4 -175.5(4) . . . . ? C2 C3 C4 C5 2.5(6) . . . . ? C3 C4 C5 C6 0.0(7) . . . . ? C4 C5 C6 C7 -1.5(6) . . . . ? C5 C6 C7 C2 0.4(6) . . . . ? C5 C6 C7 C8 173.0(4) . . . . ? C3 C2 C7 C6 2.2(6) . . . . ? C1 C2 C7 C6 175.9(4) . . . . ? C3 C2 C7 C8 -172.0(4) . . . . ? C1 C2 C7 C8 1.7(4) . . . . ? C9 N2 C8 N1 8.5(6) . . . . ? C9 N2 C8 C7 -151.9(4) . . . . ? C1 N1 C8 N2 -152.2(4) . . . . ? B1 N1 C8 N2 14.8(6) . . . . ? C1 N1 C8 C7 12.2(4) . . . . ? B1 N1 C8 C7 179.2(3) . . . . ? C6 C7 C8 N2 -18.5(7) . . . . ? C2 C7 C8 N2 154.8(4) . . . . ? C6 C7 C8 N1 178.5(4) . . . . ? C2 C7 C8 N1 -8.1(4) . . . . ? C8 N2 C9 N3 -9.7(6) . . . . ? C8 N2 C9 C10 153.9(4) . . . . ? C16 N3 C9 N2 157.0(4) . . . . ? B1 N3 C9 N2 -12.5(6) . . . . ? C16 N3 C9 C10 -10.3(4) . . . . ? B1 N3 C9 C10 -179.8(3) . . . . ? N2 C9 C10 C11 13.0(8) . . . . ? N3 C9 C10 C11 178.5(4) . . . . ? N2 C9 C10 C15 -159.7(4) . . . . ? N3 C9 C10 C15 5.8(4) . . . . ? C15 C10 C11 C12 -2.2(7) . . . . ? C9 C10 C11 C12 -174.1(5) . . . . ? C10 C11 C12 C13 2.0(7) . . . . ? C11 C12 C13 C14 -0.2(8) . . . . ? C12 C13 C14 C15 -1.4(7) . . . . ? C13 C14 C15 C10 1.2(6) . . . . ? C13 C14 C15 C16 173.8(4) . . . . ? C11 C10 C15 C14 0.6(6) . . . . ? C9 C10 C15 C14 174.4(4) . . . . ? C11 C10 C15 C16 -173.6(4) . . . . ? C9 C10 C15 C16 0.2(5) . . . . ? C17 N4 C16 N3 9.5(6) . . . . ? C17 N4 C16 C15 -153.4(4) . . . . ? C9 N3 C16 N4 -156.1(4) . . . . ? B1 N3 C16 N4 13.4(6) . . . . ? C9 N3 C16 C15 10.4(4) . . . . ? B1 N3 C16 C15 179.9(4) . . . . ? C14 C15 C16 N4 -14.5(8) . . . . ? C10 C15 C16 N4 158.8(4) . . . . ? C14 C15 C16 N3 -179.5(4) . . . . ? C10 C15 C16 N3 -6.2(4) . . . . ? C16 N4 C17 N5 -9.2(6) . . . . ? C16 N4 C17 C18 153.9(4) . . . . ? C24 N5 C17 N4 153.4(4) . . . . ? B1 N5 C17 N4 -13.8(6) . . . . ? C24 N5 C17 C18 -13.2(4) . . . . ? B1 N5 C17 C18 179.6(3) . . . . ? N4 C17 C18 C19 19.2(8) . . . . ? N5 C17 C18 C19 -175.5(4) . . . . ? N4 C17 C18 C23 -157.3(4) . . . . ? N5 C17 C18 C23 8.0(4) . . . . ? C23 C18 C19 C20 -2.8(6) . . . . ? C17 C18 C19 C20 -179.0(4) . . . . ? C18 C19 C20 C21 2.9(6) . . . . ? C19 C20 C21 C22 0.0(7) . . . . ? C20 C21 C22 C23 -2.9(6) . . . . ? C21 C22 C23 C18 2.9(6) . . . . ? C21 C22 C23 C24 179.7(4) . . . . ? C19 C18 C23 C22 -0.1(6) . . . . ? C17 C18 C23 C22 176.9(4) . . . . ? C19 C18 C23 C24 -177.5(4) . . . . ? C17 C18 C23 C24 -0.5(4) . . . . ? C1 N6 C24 N5 8.3(6) . . . . ? C1 N6 C24 C23 -156.2(4) . . . . ? C17 N5 C24 N6 -155.0(4) . . . . ? B1 N5 C24 N6 12.0(6) . . . . ? C17 N5 C24 C23 12.8(4) . . . . ? B1 N5 C24 C23 179.8(4) . . . . ? C22 C23 C24 N6 -17.7(7) . . . . ? C18 C23 C24 N6 159.4(4) . . . . ? C22 C23 C24 N5 175.8(4) . . . . ? C18 C23 C24 N5 -7.1(4) . . . . ? B1 O1 C25 C30 13.6(7) . . . . ? B1 O1 C25 C26 -167.1(4) . . . . ? O1 C25 C26 C27 -178.6(4) . . . . ? C30 C25 C26 C27 0.7(6) . . . . ? C25 C26 C27 O2 178.7(4) . . . . ? C25 C26 C27 C28 -1.0(6) . . . . ? O2 C27 C28 C29 -178.8(4) . . . . ? C26 C27 C28 C29 0.9(7) . . . . ? C27 C28 C29 C30 -0.6(7) . . . . ? O1 C25 C30 C29 178.9(4) . . . . ? C26 C25 C30 C29 -0.4(6) . . . . ? C28 C29 C30 C25 0.4(7) . . . . ? C25 O1 B1 N3 -175.3(4) . . . . ? C25 O1 B1 N1 67.7(5) . . . . ? C25 O1 B1 N5 -57.6(6) . . . . ? C16 N3 B1 O1 96.7(4) . . . . ? C9 N3 B1 O1 -94.8(4) . . . . ? C16 N3 B1 N1 -138.2(4) . . . . ? C9 N3 B1 N1 30.3(5) . . . . ? C16 N3 B1 N5 -30.7(5) . . . . ? C9 N3 B1 N5 137.7(4) . . . . ? C8 N1 B1 O1 88.3(5) . . . . ? C1 N1 B1 O1 -106.2(4) . . . . ? C8 N1 B1 N3 -31.1(5) . . . . ? C1 N1 B1 N3 134.4(4) . . . . ? C8 N1 B1 N5 -138.8(3) . . . . ? C1 N1 B1 N5 26.8(5) . . . . ? C24 N5 B1 O1 104.8(5) . . . . ? C17 N5 B1 O1 -89.5(5) . . . . ? C24 N5 B1 N3 -135.0(4) . . . . ? C17 N5 B1 N3 30.7(5) . . . . ? C24 N5 B1 N1 -26.8(5) . . . . ? C17 N5 B1 N1 138.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O N2 0.87(6) 1.98(6) 2.819(5) 161(5) 2_666 _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 66.13 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.365 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.068 _iucr_refine_instructions_details ; TITL cu_d1257_0m in P-1 CELL 1.54178 8.9397 12.8974 13.0121 105.828 109.874 99.661 ZERR 2.00 0.0005 0.0008 0.0007 0.003 0.003 0.003 LATT 1 SFAC C H N O B Cl UNIT 61.37 38 12 4.63 2 2.75 TEMP -123.150 SIZE 0.030 0.160 0.230 ACTA L.S. 4 OMIT -1 1 2 FMAP 2 PLAN 20 HTAB EQIV $1 -x+1, -y+1, -z+1 HTAB O2 N2_$1 BOND $H HTAB CONF WGHT 0.000000 4.104500 FVAR 0.25725 0.68971 O1 4 0.580970 0.728580 0.624871 11.00000 0.03805 0.04281 = 0.02706 0.01731 0.01276 0.02187 O2 4 0.593040 0.685448 0.253856 11.00000 0.05862 0.03679 = 0.03360 0.01458 0.02287 0.02095 H2O 2 0.612119 0.621991 0.257522 11.00000 -1.50000 N1 3 0.351536 0.685273 0.688727 11.00000 0.03029 0.02913 = 0.02463 0.00824 0.00620 0.01077 N2 3 0.424607 0.534940 0.746599 11.00000 0.03412 0.02804 = 0.02636 0.00689 0.00707 0.01158 N3 3 0.630053 0.707045 0.807743 11.00000 0.03012 0.03418 = 0.02559 0.01023 0.00836 0.01216 N4 3 0.800586 0.889042 0.940787 11.00000 0.03064 0.03924 = 0.03235 0.01496 0.01056 0.00874 N5 3 0.542953 0.865588 0.788118 11.00000 0.03023 0.03040 = 0.02737 0.01069 0.00947 0.01046 N6 3 0.253910 0.847637 0.717222 11.00000 0.03088 0.02968 = 0.02955 0.01086 0.00909 0.01142 C1 1 0.225869 0.734885 0.680147 11.00000 0.03201 0.02777 = 0.02502 0.00860 0.00784 0.01395 C2 1 0.080231 0.646127 0.654994 11.00000 0.03369 0.02898 = 0.02448 0.00651 0.00765 0.01071 C3 1 -0.081058 0.646980 0.640242 11.00000 0.03292 0.03677 = 0.02914 0.01037 0.00616 0.01354 AFIX 43 H3A 2 -0.115337 0.712890 0.640689 11.00000 -1.20000 AFIX 0 C4 1 -0.190636 0.547767 0.624779 11.00000 0.02987 0.04005 = 0.03357 0.00873 0.00636 0.00900 AFIX 43 H4A 2 -0.302665 0.545429 0.611360 11.00000 -1.20000 AFIX 0 C5 1 -0.139884 0.451766 0.628519 11.00000 0.03326 0.03527 = 0.03120 0.00794 0.00431 0.00356 AFIX 43 H5A 2 -0.217917 0.385562 0.617610 11.00000 -1.20000 AFIX 0 C6 1 0.022351 0.451233 0.647864 11.00000 0.03795 0.02896 = 0.02478 0.00547 0.00315 0.00768 AFIX 43 H6A 2 0.057348 0.386369 0.652194 11.00000 -1.20000 AFIX 0 C7 1 0.132035 0.548751 0.660706 11.00000 0.03193 0.02961 = 0.02106 0.00594 0.00393 0.00944 C8 1 0.310515 0.579696 0.692932 11.00000 0.03459 0.02334 = 0.02609 0.00546 0.00932 0.01214 C9 1 0.581346 0.601378 0.810723 11.00000 0.03454 0.02948 = 0.02831 0.01036 0.01125 0.01426 C10 1 0.714233 0.596112 0.909710 11.00000 0.03186 0.03308 = 0.02796 0.01091 0.00870 0.01334 C11 1 0.733984 0.511807 0.957657 11.00000 0.03998 0.03872 = 0.03908 0.01541 0.00787 0.01293 AFIX 43 H11A 2 0.655401 0.439368 0.920461 11.00000 -1.20000 AFIX 0 C12 1 0.870647 0.536752 1.060385 11.00000 0.04700 0.04381 = 0.03958 0.02095 0.00498 0.01540 AFIX 43 H12A 2 0.888174 0.479989 1.092940 11.00000 -1.20000 AFIX 0 C13 1 0.983710 0.644440 1.117238 11.00000 0.04241 0.05141 = 0.03358 0.01920 0.00303 0.01478 AFIX 43 H13A 2 1.076338 0.659115 1.187951 11.00000 -1.20000 AFIX 0 C14 1 0.964805 0.729922 1.073770 11.00000 0.03178 0.04276 = 0.03558 0.01588 0.00661 0.00902 AFIX 43 H14A 2 1.041118 0.803136 1.114095 11.00000 -1.20000 AFIX 0 C15 1 0.828490 0.704797 0.967603 11.00000 0.03270 0.04276 = 0.03099 0.01741 0.01254 0.01754 C16 1 0.766007 0.776128 0.904999 11.00000 0.02813 0.03220 = 0.03117 0.00986 0.01025 0.00795 C17 1 0.683178 0.931400 0.886706 11.00000 0.03130 0.03315 = 0.02762 0.01114 0.01088 0.00721 C18 1 0.651801 1.037705 0.928111 11.00000 0.03770 0.03197 = 0.03035 0.01318 0.01561 0.00936 C19 1 0.751141 1.138341 1.019320 11.00000 0.04120 0.03804 = 0.02988 0.01129 0.01241 0.00411 AFIX 43 H19A 2 0.862801 1.146380 1.067199 11.00000 -1.20000 AFIX 0 C20 1 0.682141 1.226087 1.037944 11.00000 0.05315 0.02971 = 0.03323 0.00593 0.01822 0.00253 AFIX 43 H20A 2 0.749546 1.296469 1.097461 11.00000 -1.20000 AFIX 0 C21 1 0.516491 1.214446 0.971991 11.00000 0.05584 0.03046 = 0.03612 0.01063 0.02535 0.01500 AFIX 43 H21A 2 0.473623 1.276842 0.987427 11.00000 -1.20000 AFIX 0 C22 1 0.412454 1.112666 0.883624 11.00000 0.04109 0.03265 = 0.03176 0.00950 0.01692 0.01145 AFIX 43 H22A 2 0.298223 1.103267 0.840850 11.00000 -1.20000 AFIX 0 C23 1 0.483241 1.025908 0.861056 11.00000 0.03967 0.02768 = 0.02888 0.00935 0.01623 0.00833 C24 1 0.412143 0.910467 0.776886 11.00000 0.03585 0.02833 = 0.02806 0.01125 0.01281 0.01278 C25 1 0.531695 0.758162 0.528012 11.00000 0.03107 0.02964 = 0.02425 0.00958 0.00634 0.00830 C26 1 0.582230 0.707081 0.441454 11.00000 0.03222 0.02752 = 0.02717 0.01023 0.00933 0.01045 AFIX 43 H26A 2 0.643963 0.654750 0.451860 11.00000 -1.20000 AFIX 0 C27 1 0.542142 0.732786 0.339206 11.00000 0.04050 0.02481 = 0.02667 0.00684 0.01247 0.00644 C28 1 0.450449 0.807316 0.323366 11.00000 0.05435 0.04133 = 0.03540 0.02064 0.01838 0.02144 AFIX 43 H28A 2 0.421548 0.824164 0.253712 11.00000 -1.20000 AFIX 0 C29 1 0.400716 0.857466 0.409462 11.00000 0.04980 0.03935 = 0.04040 0.01985 0.01589 0.02296 AFIX 43 H29A 2 0.338399 0.909425 0.398702 11.00000 -1.20000 AFIX 0 C30 1 0.440518 0.833043 0.511901 11.00000 0.04518 0.03702 = 0.02954 0.01075 0.01465 0.01892 AFIX 43 H30A 2 0.405004 0.867801 0.570162 11.00000 -1.20000 AFIX 0 B1 5 0.527000 0.747387 0.718127 11.00000 0.03321 0.03136 = 0.02522 0.00911 0.00894 0.01398 PART 1 CL1 6 0.915549 0.966886 0.751263 21.00000 0.05346 0.03573 = 0.04398 0.01223 0.03168 0.00566 CL2 6 1.027735 1.106708 0.635664 21.00000 0.05850 0.03655 = 0.04304 0.01609 0.02621 0.00564 C1S 1 0.937187 0.967757 0.622478 21.00000 0.03507 0.02813 = 0.03633 0.00934 0.01616 0.00652 AFIX 23 H1SA 2 0.826802 0.936233 0.556033 21.00000 -1.20000 H1SB 2 1.008016 0.919739 0.606274 21.00000 -1.20000 AFIX 0 PART 2 O1W 4 1.024405 1.106612 0.573399 -21.00000 0.16475 0.10934 = 0.06747 0.00901 0.02349 0.01712 AFIX 3 H1WA 2 0.938655 1.062772 0.567669 -21.00000 -1.50000 H1WB 2 1.047245 1.137472 0.529339 -21.00000 -1.50000 PART 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_d1257_0m in P-1 REM R1 = 0.0674 for 4025 Fo > 4sig(Fo) and 0.0697 for all 4276 data REM 392 parameters refined using 0 restraints END WGHT 0.0000 4.1033 REM Highest difference peak 0.365, deepest hole -0.277, 1-sigma level 0.068 Q1 1 0.6639 0.7770 0.6290 11.00000 0.05 0.37 Q2 1 0.9229 0.9719 0.6892 11.00000 0.05 0.34 Q3 1 0.4753 0.6293 0.2367 11.00000 0.05 0.29 Q4 1 0.7287 0.7441 0.7942 11.00000 0.05 0.28 Q5 1 0.9351 0.4339 1.0986 11.00000 0.05 0.27 Q6 1 0.8177 0.8210 0.8627 11.00000 0.05 0.26 Q7 1 0.2022 0.8569 0.7750 11.00000 0.05 0.25 Q8 1 1.1743 0.6865 1.2187 11.00000 0.05 0.24 Q9 1 0.8114 0.6413 0.9100 11.00000 0.05 0.24 Q10 1 0.0715 0.3459 0.6336 11.00000 0.05 0.24 Q11 1 0.0681 0.6818 0.7572 11.00000 0.05 0.24 Q12 1 0.4882 0.5385 0.7060 11.00000 0.05 0.24 Q13 1 0.8986 1.0009 0.4606 11.00000 0.05 0.23 Q14 1 0.8925 0.9413 0.5144 11.00000 0.05 0.23 Q15 1 0.7184 0.4175 0.8604 11.00000 0.05 0.23 Q16 1 -0.1278 0.5427 0.7374 11.00000 0.05 0.23 Q17 1 0.4055 0.7297 0.3180 11.00000 0.05 0.22 Q18 1 0.2272 1.0154 0.7262 11.00000 0.05 0.21 Q19 1 0.3383 0.8280 0.1194 11.00000 0.05 0.21 Q20 1 -0.1701 0.7678 0.7175 11.00000 0.05 0.21 ; _vrf_PLAT770_d1257 ; PROBLEM: Suspect C-H Bond in CIF: C1S -- H1WA .. 1.58 Ang. RESPONSE: The bond does not exist as partial occupancy dichloromethane and water molecules are disordered in the same vicinity with refined occupancy parameters of 0.690(5) and 0.310(5). ; # end Validation Reply Form _vrf_PLAT029_d1257 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.943 RESPONSE: Data were collected on a very thin plate using CuKalpha radiation using a Bruker Microsource system eqipped with multi layer optics. Without this type of instrumentation we would not have been able to collect sufficient data to aquire a crystal structure. We feel that the precision of the structure is good enough to support any claims made regadring the geometry of the molecule and the intermolecular distances. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 949040' ####################################################################### # # 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_d12333 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-Hydroxyphenolato)(subphthalocyaninato)boron ; _chemical_name_common ; p-HOPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H17 B N6 O2' _chemical_formula_sum 'C30 H17 B N6 O2' _chemical_formula_weight 504.31 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' _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 9.8450(9) _cell_length_b 11.2012(10) _cell_length_c 12.2165(10) _cell_angle_alpha 107.938(2) _cell_angle_beta 106.262(2) _cell_angle_gamma 101.412(2) _cell_volume 1169.37(18) _cell_formula_units_Z 2 _cell_measurement_temperature 147(2) _cell_measurement_reflns_used 9407 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7044 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SABADS (Shedrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 147(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Bruker Triumph' _diffrn_measurement_device_type 'Bruker Kappa APEX-DUO CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17972 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5363 _reflns_number_gt 4367 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0488P)^2^+0.2799P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5363 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O1 O 0.68273(11) 0.87449(9) 0.44195(8) 0.0236(2) Uani 1 1 d . . . O2 O 0.46674(12) 0.77223(10) 0.78669(9) 0.0309(2) Uani 1 1 d . . . H1O H 0.434(2) 0.684(2) 0.7718(18) 0.051(6) Uiso 1 1 d . . . N1 N 0.81365(12) 0.71646(10) 0.35658(9) 0.0198(2) Uani 1 1 d . . . N2 N 1.00965(12) 0.87676(11) 0.35243(10) 0.0228(2) Uani 1 1 d . . . N3 N 0.75911(12) 0.87440(10) 0.27474(9) 0.0189(2) Uani 1 1 d . . . N4 N 0.52350(12) 0.81881(10) 0.11793(10) 0.0195(2) Uani 1 1 d . . . N5 N 0.56690(12) 0.68663(10) 0.23552(9) 0.0184(2) Uani 1 1 d . . . N6 N 0.63307(12) 0.50323(10) 0.26456(9) 0.0192(2) Uani 1 1 d . . . C1 C 0.77461(14) 0.58335(12) 0.32819(11) 0.0199(3) Uani 1 1 d . . . C2 C 0.91296(15) 0.55059(13) 0.35334(11) 0.0221(3) Uani 1 1 d . . . C3 C 0.94064(16) 0.43042(14) 0.33932(12) 0.0263(3) Uani 1 1 d . . . H3A H 0.8626 0.3519 0.3165 0.032 Uiso 1 1 calc R . . C4 C 1.08608(17) 0.42978(15) 0.35985(13) 0.0327(3) Uani 1 1 d . . . H4A H 1.1084 0.3496 0.3522 0.039 Uiso 1 1 calc R . . C5 C 1.20082(17) 0.54491(16) 0.39170(14) 0.0356(4) Uani 1 1 d . . . H5A H 1.2993 0.5408 0.4051 0.043 Uiso 1 1 calc R . . C6 C 1.17507(16) 0.66470(15) 0.40433(13) 0.0299(3) Uani 1 1 d . . . H6A H 1.2537 0.7421 0.4256 0.036 Uiso 1 1 calc R . . C7 C 1.02931(15) 0.66744(14) 0.38471(12) 0.0237(3) Uani 1 1 d . . . C8 C 0.96039(14) 0.76928(13) 0.37487(11) 0.0218(3) Uani 1 1 d . . . C9 C 0.90639(14) 0.92290(12) 0.29587(11) 0.0201(3) Uani 1 1 d . . . C10 C 0.91315(15) 1.00046(12) 0.21996(11) 0.0208(3) Uani 1 1 d . . . C11 C 1.03240(15) 1.07287(13) 0.20276(12) 0.0245(3) Uani 1 1 d . . . H11A H 1.1324 1.0843 0.2497 0.029 Uiso 1 1 calc R . . C12 C 1.00008(16) 1.12737(14) 0.11503(13) 0.0281(3) Uani 1 1 d . . . H12A H 1.0796 1.1790 0.1033 0.034 Uiso 1 1 calc R . . C13 C 0.85333(16) 1.10837(14) 0.04309(13) 0.0272(3) Uani 1 1 d . . . H13A H 0.8356 1.1470 -0.0166 0.033 Uiso 1 1 calc R . . C14 C 0.73330(16) 1.03448(13) 0.05680(12) 0.0233(3) Uani 1 1 d . . . H14A H 0.6339 1.0207 0.0068 0.028 Uiso 1 1 calc R . . C15 C 0.76371(14) 0.98111(12) 0.14668(12) 0.0201(3) Uani 1 1 d . . . C16 C 0.66712(14) 0.89260(12) 0.17872(11) 0.0188(3) Uani 1 1 d . . . C17 C 0.47800(14) 0.71256(12) 0.14322(11) 0.0191(3) Uani 1 1 d . . . C18 C 0.35300(14) 0.59187(13) 0.07016(12) 0.0203(3) Uani 1 1 d . . . C19 C 0.22017(15) 0.56203(14) -0.02661(12) 0.0242(3) Uani 1 1 d . . . H19A H 0.1982 0.6265 -0.0582 0.029 Uiso 1 1 calc R . . C20 C 0.12105(15) 0.43585(14) -0.07554(12) 0.0265(3) Uani 1 1 d . . . H20A H 0.0270 0.4152 -0.1379 0.032 Uiso 1 1 calc R . . C21 C 0.15672(16) 0.33794(14) -0.03480(12) 0.0262(3) Uani 1 1 d . . . H21A H 0.0872 0.2517 -0.0717 0.031 Uiso 1 1 calc R . . C22 C 0.29090(15) 0.36376(13) 0.05800(12) 0.0233(3) Uani 1 1 d . . . H22A H 0.3160 0.2961 0.0830 0.028 Uiso 1 1 calc R . . C23 C 0.38786(14) 0.49288(13) 0.11341(11) 0.0197(3) Uani 1 1 d . . . C24 C 0.53231(14) 0.55568(12) 0.21420(11) 0.0186(3) Uani 1 1 d . . . C25 C 0.63084(14) 0.84026(12) 0.52416(11) 0.0184(3) Uani 1 1 d . . . C26 C 0.60198(15) 0.93934(13) 0.60754(12) 0.0235(3) Uani 1 1 d . . . H26A H 0.6189 1.0246 0.6045 0.028 Uiso 1 1 calc R . . C27 C 0.54904(16) 0.91502(14) 0.69458(13) 0.0263(3) Uani 1 1 d . . . H27A H 0.5303 0.9838 0.7510 0.032 Uiso 1 1 calc R . . C28 C 0.52297(15) 0.79094(13) 0.70041(12) 0.0217(3) Uani 1 1 d . . . C29 C 0.55593(14) 0.69313(12) 0.62029(12) 0.0207(3) Uani 1 1 d . . . H29A H 0.5422 0.6090 0.6255 0.025 Uiso 1 1 calc R . . C30 C 0.60914(14) 0.71730(13) 0.53205(11) 0.0210(3) Uani 1 1 d . . . H30A H 0.6306 0.6493 0.4772 0.025 Uiso 1 1 calc R . . B1 B 0.70325(16) 0.79060(14) 0.33712(13) 0.0189(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0328(5) 0.0186(5) 0.0212(5) 0.0083(4) 0.0133(4) 0.0058(4) O2 0.0466(7) 0.0242(5) 0.0330(5) 0.0122(4) 0.0278(5) 0.0128(5) N1 0.0208(6) 0.0192(5) 0.0177(5) 0.0078(4) 0.0056(4) 0.0038(4) N2 0.0208(6) 0.0215(6) 0.0199(5) 0.0073(4) 0.0024(4) 0.0022(5) N3 0.0199(6) 0.0172(5) 0.0192(5) 0.0071(4) 0.0069(4) 0.0050(4) N4 0.0194(5) 0.0193(5) 0.0232(5) 0.0095(4) 0.0101(4) 0.0076(4) N5 0.0193(5) 0.0177(5) 0.0201(5) 0.0086(4) 0.0083(4) 0.0057(4) N6 0.0226(6) 0.0195(5) 0.0181(5) 0.0089(4) 0.0094(4) 0.0064(4) C1 0.0246(7) 0.0195(6) 0.0165(6) 0.0082(5) 0.0076(5) 0.0063(5) C2 0.0241(7) 0.0257(7) 0.0163(6) 0.0097(5) 0.0050(5) 0.0083(5) C3 0.0298(8) 0.0257(7) 0.0202(6) 0.0083(5) 0.0043(5) 0.0102(6) C4 0.0346(8) 0.0302(8) 0.0277(7) 0.0071(6) 0.0030(6) 0.0169(7) C5 0.0247(8) 0.0405(9) 0.0332(8) 0.0091(7) 0.0014(6) 0.0143(7) C6 0.0219(7) 0.0333(8) 0.0275(7) 0.0103(6) 0.0018(5) 0.0067(6) C7 0.0238(7) 0.0264(7) 0.0180(6) 0.0092(5) 0.0031(5) 0.0070(6) C8 0.0200(7) 0.0224(7) 0.0173(6) 0.0063(5) 0.0025(5) 0.0030(5) C9 0.0203(6) 0.0167(6) 0.0184(6) 0.0045(5) 0.0055(5) 0.0013(5) C10 0.0238(7) 0.0164(6) 0.0208(6) 0.0061(5) 0.0083(5) 0.0048(5) C11 0.0227(7) 0.0202(6) 0.0259(7) 0.0070(5) 0.0079(5) 0.0014(5) C12 0.0296(8) 0.0240(7) 0.0318(7) 0.0123(6) 0.0149(6) 0.0027(6) C13 0.0336(8) 0.0248(7) 0.0281(7) 0.0149(6) 0.0131(6) 0.0090(6) C14 0.0264(7) 0.0213(7) 0.0251(7) 0.0110(5) 0.0100(5) 0.0093(5) C15 0.0232(7) 0.0165(6) 0.0222(6) 0.0068(5) 0.0105(5) 0.0069(5) C16 0.0215(6) 0.0169(6) 0.0206(6) 0.0077(5) 0.0096(5) 0.0083(5) C17 0.0195(6) 0.0199(6) 0.0206(6) 0.0080(5) 0.0096(5) 0.0083(5) C18 0.0202(6) 0.0204(6) 0.0215(6) 0.0076(5) 0.0104(5) 0.0056(5) C19 0.0227(7) 0.0282(7) 0.0228(6) 0.0107(6) 0.0088(5) 0.0079(6) C20 0.0210(7) 0.0320(8) 0.0200(6) 0.0067(6) 0.0056(5) 0.0029(6) C21 0.0259(7) 0.0229(7) 0.0227(7) 0.0041(5) 0.0094(5) -0.0010(5) C22 0.0255(7) 0.0211(7) 0.0228(6) 0.0073(5) 0.0113(5) 0.0044(5) C23 0.0201(6) 0.0210(6) 0.0199(6) 0.0074(5) 0.0108(5) 0.0062(5) C24 0.0206(6) 0.0176(6) 0.0189(6) 0.0072(5) 0.0099(5) 0.0045(5) C25 0.0169(6) 0.0204(6) 0.0161(6) 0.0071(5) 0.0044(5) 0.0040(5) C26 0.0288(7) 0.0187(6) 0.0258(7) 0.0101(5) 0.0109(6) 0.0097(6) C27 0.0351(8) 0.0227(7) 0.0277(7) 0.0094(6) 0.0172(6) 0.0151(6) C28 0.0232(7) 0.0235(7) 0.0206(6) 0.0089(5) 0.0101(5) 0.0085(5) C29 0.0232(7) 0.0163(6) 0.0225(6) 0.0074(5) 0.0089(5) 0.0055(5) C30 0.0237(7) 0.0183(6) 0.0198(6) 0.0048(5) 0.0090(5) 0.0071(5) B1 0.0211(7) 0.0178(7) 0.0172(6) 0.0073(5) 0.0068(5) 0.0041(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C25 1.3652(15) . ? O1 B1 1.4291(16) . ? O2 C28 1.3706(15) . ? O2 H1O 0.92(2) . ? N1 C1 1.3679(16) . ? N1 C8 1.3735(17) . ? N1 B1 1.5039(18) . ? N2 C8 1.3441(17) . ? N2 C9 1.3463(16) . ? N3 C9 1.3625(16) . ? N3 C16 1.3650(16) . ? N3 B1 1.4951(17) . ? N4 C16 1.3436(17) . ? N4 C17 1.3437(16) . ? N5 C24 1.3611(16) . ? N5 C17 1.3681(16) . ? N5 B1 1.5022(18) . ? N6 C24 1.3487(16) . ? N6 C1 1.3492(17) . ? C1 C2 1.4550(18) . ? C2 C3 1.3945(19) . ? C2 C7 1.4227(19) . ? C3 C4 1.385(2) . ? C3 H3A 0.9500 . ? C4 C5 1.400(2) . ? C4 H4A 0.9500 . ? C5 C6 1.385(2) . ? C5 H5A 0.9500 . ? C6 C7 1.3953(19) . ? C6 H6A 0.9500 . ? C7 C8 1.4564(19) . ? C9 C10 1.4585(18) . ? C10 C11 1.3952(18) . ? C10 C15 1.4247(18) . ? C11 C12 1.383(2) . ? C11 H11A 0.9500 . ? C12 C13 1.399(2) . ? C12 H12A 0.9500 . ? C13 C14 1.3851(19) . ? C13 H13A 0.9500 . ? C14 C15 1.3941(18) . ? C14 H14A 0.9500 . ? C15 C16 1.4543(17) . ? C17 C18 1.4566(18) . ? C18 C19 1.3919(18) . ? C18 C23 1.4270(18) . ? C19 C20 1.384(2) . ? C19 H19A 0.9500 . ? C20 C21 1.402(2) . ? C20 H20A 0.9500 . ? C21 C22 1.3863(19) . ? C21 H21A 0.9500 . ? C22 C23 1.3964(18) . ? C22 H22A 0.9500 . ? C23 C24 1.4571(18) . ? C25 C30 1.3888(17) . ? C25 C26 1.3931(17) . ? C26 C27 1.3817(19) . ? C26 H26A 0.9500 . ? C27 C28 1.3901(19) . ? C27 H27A 0.9500 . ? C28 C29 1.3862(17) . ? C29 C30 1.3963(17) . ? 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 128.30(10) . . ? C28 O2 H1O 110.9(12) . . ? C1 N1 C8 112.32(11) . . ? C1 N1 B1 123.89(11) . . ? C8 N1 B1 121.91(11) . . ? C8 N2 C9 117.19(11) . . ? C9 N3 C16 113.60(10) . . ? C9 N3 B1 122.84(11) . . ? C16 N3 B1 122.87(11) . . ? C16 N4 C17 116.91(11) . . ? C24 N5 C17 112.95(10) . . ? C24 N5 B1 124.23(11) . . ? C17 N5 B1 122.03(10) . . ? C24 N6 C1 117.27(11) . . ? N6 C1 N1 122.52(11) . . ? N6 C1 C2 129.68(12) . . ? N1 C1 C2 106.29(11) . . ? C3 C2 C7 121.18(12) . . ? C3 C2 C1 131.52(13) . . ? C7 C2 C1 106.93(11) . . ? C4 C3 C2 117.51(14) . . ? C4 C3 H3A 121.2 . . ? C2 C3 H3A 121.2 . . ? C3 C4 C5 121.34(14) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C6 C5 C4 121.95(14) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C5 C6 C7 117.53(14) . . ? C5 C6 H6A 121.2 . . ? C7 C6 H6A 121.2 . . ? C6 C7 C2 120.48(13) . . ? C6 C7 C8 131.90(13) . . ? C2 C7 C8 107.18(11) . . ? N2 C8 N1 122.74(12) . . ? N2 C8 C7 129.10(12) . . ? N1 C8 C7 105.79(11) . . ? N2 C9 N3 122.37(11) . . ? N2 C9 C10 130.36(12) . . ? N3 C9 C10 105.48(11) . . ? C11 C10 C15 120.58(12) . . ? C11 C10 C9 132.01(12) . . ? C15 C10 C9 107.13(11) . . ? C12 C11 C10 117.71(13) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C13 121.68(13) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C14 C13 C12 121.55(13) . . ? C14 C13 H13A 119.2 . . ? C12 C13 H13A 119.2 . . ? C13 C14 C15 117.59(13) . . ? C13 C14 H14A 121.2 . . ? C15 C14 H14A 121.2 . . ? C14 C15 C10 120.87(12) . . ? C14 C15 C16 131.79(12) . . ? C10 C15 C16 107.12(11) . . ? N4 C16 N3 122.57(11) . . ? N4 C16 C15 130.56(11) . . ? N3 C16 C15 105.64(11) . . ? N4 C17 N5 122.55(11) . . ? N4 C17 C18 130.48(11) . . ? N5 C17 C18 105.44(11) . . ? C19 C18 C23 120.54(12) . . ? C19 C18 C17 132.39(12) . . ? C23 C18 C17 107.06(11) . . ? C20 C19 C18 118.09(13) . . ? C20 C19 H19A 121.0 . . ? C18 C19 H19A 121.0 . . ? C19 C20 C21 121.25(13) . . ? C19 C20 H20A 119.4 . . ? C21 C20 H20A 119.4 . . ? C22 C21 C20 121.68(13) . . ? C22 C21 H21A 119.2 . . ? C20 C21 H21A 119.2 . . ? C21 C22 C23 117.55(13) . . ? C21 C22 H22A 121.2 . . ? C23 C22 H22A 121.2 . . ? C22 C23 C18 120.71(12) . . ? C22 C23 C24 132.50(12) . . ? C18 C23 C24 106.78(11) . . ? N6 C24 N5 122.03(11) . . ? N6 C24 C23 130.82(11) . . ? N5 C24 C23 105.89(11) . . ? O1 C25 C30 125.10(11) . . ? O1 C25 C26 116.07(11) . . ? C30 C25 C26 118.81(11) . . ? C27 C26 C25 120.72(12) . . ? C27 C26 H26A 119.6 . . ? C25 C26 H26A 119.6 . . ? C26 C27 C28 120.64(12) . . ? C26 C27 H27A 119.7 . . ? C28 C27 H27A 119.7 . . ? O2 C28 C29 123.30(12) . . ? O2 C28 C27 117.78(11) . . ? C29 C28 C27 118.91(12) . . ? C28 C29 C30 120.56(12) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C25 C30 C29 120.30(11) . . ? C25 C30 H30A 119.8 . . ? C29 C30 H30A 119.8 . . ? O1 B1 N3 107.98(10) . . ? O1 B1 N5 117.16(11) . . ? N3 B1 N5 103.37(10) . . ? O1 B1 N1 119.20(11) . . ? N3 B1 N1 103.96(10) . . ? N5 B1 N1 103.36(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 N6 C1 N1 8.93(17) . . . . ? C24 N6 C1 C2 -155.04(12) . . . . ? C8 N1 C1 N6 -155.45(11) . . . . ? B1 N1 C1 N6 9.16(18) . . . . ? C8 N1 C1 C2 11.76(14) . . . . ? B1 N1 C1 C2 176.37(11) . . . . ? N6 C1 C2 C3 -12.7(2) . . . . ? N1 C1 C2 C3 -178.64(13) . . . . ? N6 C1 C2 C7 160.17(12) . . . . ? N1 C1 C2 C7 -5.79(13) . . . . ? C7 C2 C3 C4 1.45(19) . . . . ? C1 C2 C3 C4 173.45(13) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? C5 C6 C7 C2 0.2(2) . . . . ? C5 C6 C7 C8 -171.10(14) . . . . ? C3 C2 C7 C6 -1.11(19) . . . . ? C1 C2 C7 C6 -174.86(12) . . . . ? C3 C2 C7 C8 172.12(11) . . . . ? C1 C2 C7 C8 -1.63(14) . . . . ? C9 N2 C8 N1 -8.17(18) . . . . ? C9 N2 C8 C7 151.78(13) . . . . ? C1 N1 C8 N2 151.21(12) . . . . ? B1 N1 C8 N2 -13.74(18) . . . . ? C1 N1 C8 C7 -12.73(14) . . . . ? B1 N1 C8 C7 -177.68(10) . . . . ? C6 C7 C8 N2 18.0(2) . . . . ? C2 C7 C8 N2 -154.15(13) . . . . ? C6 C7 C8 N1 -179.44(14) . . . . ? C2 C7 C8 N1 8.41(14) . . . . ? C8 N2 C9 N3 7.72(18) . . . . ? C8 N2 C9 C10 -154.72(13) . . . . ? C16 N3 C9 N2 -155.79(11) . . . . ? B1 N3 C9 N2 14.93(18) . . . . ? C16 N3 C9 C10 10.40(14) . . . . ? B1 N3 C9 C10 -178.87(11) . . . . ? N2 C9 C10 C11 -15.1(2) . . . . ? N3 C9 C10 C11 -179.82(13) . . . . ? N2 C9 C10 C15 158.56(13) . . . . ? N3 C9 C10 C15 -6.11(13) . . . . ? C15 C10 C11 C12 1.66(19) . . . . ? C9 C10 C11 C12 174.67(13) . . . . ? C10 C11 C12 C13 -1.7(2) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 C15 1.0(2) . . . . ? C13 C14 C15 C10 -1.03(19) . . . . ? C13 C14 C15 C16 -174.80(13) . . . . ? C11 C10 C15 C14 -0.32(19) . . . . ? C9 C10 C15 C14 -174.90(11) . . . . ? C11 C10 C15 C16 174.82(11) . . . . ? C9 C10 C15 C16 0.25(13) . . . . ? C17 N4 C16 N3 -9.46(17) . . . . ? C17 N4 C16 C15 155.98(12) . . . . ? C9 N3 C16 N4 158.29(11) . . . . ? B1 N3 C16 N4 -12.43(18) . . . . ? C9 N3 C16 C15 -10.27(14) . . . . ? B1 N3 C16 C15 179.01(11) . . . . ? C14 C15 C16 N4 12.8(2) . . . . ? C10 C15 C16 N4 -161.60(12) . . . . ? C14 C15 C16 N3 -179.89(13) . . . . ? C10 C15 C16 N3 5.70(13) . . . . ? C16 N4 C17 N5 6.96(17) . . . . ? C16 N4 C17 C18 -156.79(12) . . . . ? C24 N5 C17 N4 -152.98(11) . . . . ? B1 N5 C17 N4 17.32(17) . . . . ? C24 N5 C17 C18 14.26(13) . . . . ? B1 N5 C17 C18 -175.43(10) . . . . ? N4 C17 C18 C19 -22.0(2) . . . . ? N5 C17 C18 C19 172.20(13) . . . . ? N4 C17 C18 C23 156.87(12) . . . . ? N5 C17 C18 C23 -8.96(13) . . . . ? C23 C18 C19 C20 2.69(18) . . . . ? C17 C18 C19 C20 -178.61(12) . . . . ? C18 C19 C20 C21 -4.08(19) . . . . ? C19 C20 C21 C22 1.5(2) . . . . ? C20 C21 C22 C23 2.44(19) . . . . ? C21 C22 C23 C18 -3.77(18) . . . . ? C21 C22 C23 C24 177.53(12) . . . . ? C19 C18 C23 C22 1.26(18) . . . . ? C17 C18 C23 C22 -177.74(11) . . . . ? C19 C18 C23 C24 -179.74(11) . . . . ? C17 C18 C23 C24 1.26(13) . . . . ? C1 N6 C24 N5 -6.09(17) . . . . ? C1 N6 C24 C23 159.18(12) . . . . ? C17 N5 C24 N6 154.94(11) . . . . ? B1 N5 C24 N6 -15.12(18) . . . . ? C17 N5 C24 C23 -13.52(13) . . . . ? B1 N5 C24 C23 176.42(10) . . . . ? C22 C23 C24 N6 18.8(2) . . . . ? C18 C23 C24 N6 -160.08(12) . . . . ? C22 C23 C24 N5 -174.20(13) . . . . ? C18 C23 C24 N5 6.97(13) . . . . ? B1 O1 C25 C30 10.6(2) . . . . ? B1 O1 C25 C26 -171.12(12) . . . . ? O1 C25 C26 C27 179.96(12) . . . . ? C30 C25 C26 C27 -1.6(2) . . . . ? C25 C26 C27 C28 -0.2(2) . . . . ? C26 C27 C28 O2 -178.31(13) . . . . ? C26 C27 C28 C29 2.3(2) . . . . ? O2 C28 C29 C30 178.21(12) . . . . ? C27 C28 C29 C30 -2.4(2) . . . . ? O1 C25 C30 C29 179.74(12) . . . . ? C26 C25 C30 C29 1.51(19) . . . . ? C28 C29 C30 C25 0.5(2) . . . . ? C25 O1 B1 N3 178.65(11) . . . . ? C25 O1 B1 N5 62.55(17) . . . . ? C25 O1 B1 N1 -63.19(17) . . . . ? C9 N3 B1 O1 96.20(13) . . . . ? C16 N3 B1 O1 -93.93(13) . . . . ? C9 N3 B1 N5 -139.02(11) . . . . ? C16 N3 B1 N5 30.85(15) . . . . ? C9 N3 B1 N1 -31.33(15) . . . . ? C16 N3 B1 N1 138.54(11) . . . . ? C24 N5 B1 O1 -105.30(14) . . . . ? C17 N5 B1 O1 85.51(14) . . . . ? C24 N5 B1 N3 136.11(11) . . . . ? C17 N5 B1 N3 -33.08(14) . . . . ? C24 N5 B1 N1 27.97(15) . . . . ? C17 N5 B1 N1 -141.23(11) . . . . ? C1 N1 B1 O1 107.13(14) . . . . ? C8 N1 B1 O1 -89.68(15) . . . . ? C1 N1 B1 N3 -132.64(11) . . . . ? C8 N1 B1 N3 30.54(15) . . . . ? C1 N1 B1 N5 -24.95(15) . . . . ? C8 N1 B1 N5 138.24(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1O N6 0.92(2) 1.93(2) 2.8537(15) 177.9(18) 2_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.241 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.047 _iucr_refine_instructions_details ; TITL mo_d12333_0m in P-1 CELL 0.71073 9.8450 11.2012 12.2165 107.938 106.262 101.412 ZERR 2.00 0.0009 0.0010 0.0010 0.002 0.002 0.002 LATT 1 SFAC C H N O B UNIT 60 34 12 4 2 TEMP -126.150 SIZE 0.250 0.260 0.340 ACTA L.S. 4 FMAP 2 PLAN 20 EQIV $1 -x+1, -y+1, -z+1 HTAB O2 N6_$1 HTAB BOND $H CONF WGHT 0.048800 0.279900 FVAR 0.23603 O1 4 0.682731 0.874490 0.441946 11.00000 0.03276 0.01861 = 0.02115 0.00828 0.01331 0.00584 O2 4 0.466738 0.772228 0.786687 11.00000 0.04658 0.02422 = 0.03298 0.01225 0.02778 0.01276 H1O 2 0.433911 0.683787 0.771849 11.00000 0.05117 N1 3 0.813654 0.716462 0.356579 11.00000 0.02078 0.01921 = 0.01771 0.00779 0.00562 0.00383 N2 3 1.009654 0.876758 0.352430 11.00000 0.02076 0.02150 = 0.01995 0.00729 0.00240 0.00220 N3 3 0.759114 0.874400 0.274745 11.00000 0.01992 0.01718 = 0.01916 0.00708 0.00686 0.00499 N4 3 0.523502 0.818806 0.117928 11.00000 0.01936 0.01925 = 0.02321 0.00948 0.01011 0.00764 N5 3 0.566905 0.686627 0.235521 11.00000 0.01931 0.01771 = 0.02005 0.00855 0.00832 0.00574 N6 3 0.633067 0.503231 0.264559 11.00000 0.02257 0.01948 = 0.01808 0.00890 0.00940 0.00641 C1 1 0.774611 0.583351 0.328186 11.00000 0.02459 0.01948 = 0.01649 0.00821 0.00756 0.00628 C2 1 0.912960 0.550588 0.353339 11.00000 0.02414 0.02571 = 0.01626 0.00970 0.00504 0.00830 C3 1 0.940644 0.430424 0.339322 11.00000 0.02981 0.02573 = 0.02019 0.00826 0.00428 0.01023 AFIX 43 H3A 2 0.862637 0.351940 0.316539 11.00000 -1.20000 AFIX 0 C4 1 1.086076 0.429780 0.359853 11.00000 0.03461 0.03024 = 0.02769 0.00711 0.00302 0.01690 AFIX 43 H4A 2 1.108430 0.349561 0.352164 11.00000 -1.20000 AFIX 0 C5 1 1.200824 0.544913 0.391705 11.00000 0.02475 0.04051 = 0.03317 0.00909 0.00141 0.01430 AFIX 43 H5A 2 1.299291 0.540757 0.405059 11.00000 -1.20000 AFIX 0 C6 1 1.175068 0.664700 0.404328 11.00000 0.02186 0.03329 = 0.02745 0.01035 0.00176 0.00667 AFIX 43 H6A 2 1.253723 0.742144 0.425558 11.00000 -1.20000 AFIX 0 C7 1 1.029314 0.667444 0.384712 11.00000 0.02378 0.02641 = 0.01799 0.00917 0.00312 0.00700 C8 1 0.960391 0.769276 0.374871 11.00000 0.01995 0.02244 = 0.01732 0.00633 0.00247 0.00297 C9 1 0.906394 0.922897 0.295873 11.00000 0.02029 0.01671 = 0.01839 0.00449 0.00551 0.00134 C10 1 0.913153 1.000464 0.219960 11.00000 0.02381 0.01642 = 0.02079 0.00606 0.00827 0.00483 C11 1 1.032402 1.072872 0.202755 11.00000 0.02275 0.02022 = 0.02587 0.00702 0.00793 0.00137 AFIX 43 H11A 2 1.132364 1.084328 0.249705 11.00000 -1.20000 AFIX 0 C12 1 1.000081 1.127375 0.115027 11.00000 0.02959 0.02399 = 0.03182 0.01226 0.01490 0.00269 AFIX 43 H12A 2 1.079562 1.179050 0.103298 11.00000 -1.20000 AFIX 0 C13 1 0.853326 1.108370 0.043090 11.00000 0.03357 0.02484 = 0.02814 0.01495 0.01314 0.00902 AFIX 43 H13A 2 0.835569 1.147049 -0.016566 11.00000 -1.20000 AFIX 0 C14 1 0.733303 1.034483 0.056803 11.00000 0.02644 0.02132 = 0.02512 0.01102 0.01004 0.00934 AFIX 43 H14A 2 0.633869 1.020675 0.006777 11.00000 -1.20000 AFIX 0 C15 1 0.763711 0.981115 0.146680 11.00000 0.02319 0.01648 = 0.02217 0.00683 0.01053 0.00688 C16 1 0.667121 0.892600 0.178723 11.00000 0.02154 0.01690 = 0.02060 0.00770 0.00957 0.00830 C17 1 0.478001 0.712562 0.143220 11.00000 0.01946 0.01991 = 0.02063 0.00801 0.00965 0.00829 C18 1 0.353005 0.591873 0.070156 11.00000 0.02024 0.02042 = 0.02147 0.00764 0.01039 0.00560 C19 1 0.220169 0.562034 -0.026612 11.00000 0.02271 0.02815 = 0.02278 0.01074 0.00883 0.00792 AFIX 43 H19A 2 0.198188 0.626457 -0.058159 11.00000 -1.20000 AFIX 0 C20 1 0.121052 0.435847 -0.075540 11.00000 0.02101 0.03198 = 0.02002 0.00673 0.00556 0.00292 AFIX 43 H20A 2 0.027045 0.415177 -0.137928 11.00000 -1.20000 AFIX 0 C21 1 0.156722 0.337942 -0.034798 11.00000 0.02591 0.02285 = 0.02265 0.00413 0.00941 -0.00096 AFIX 43 H21A 2 0.087179 0.251687 -0.071716 11.00000 -1.20000 AFIX 0 C22 1 0.290897 0.363761 0.058000 11.00000 0.02548 0.02111 = 0.02276 0.00725 0.01130 0.00445 AFIX 43 H22A 2 0.315952 0.296104 0.082975 11.00000 -1.20000 AFIX 0 C23 1 0.387860 0.492878 0.113408 11.00000 0.02007 0.02105 = 0.01993 0.00741 0.01077 0.00622 C24 1 0.532307 0.555677 0.214201 11.00000 0.02060 0.01764 = 0.01893 0.00717 0.00990 0.00447 C25 1 0.630843 0.840255 0.524157 11.00000 0.01686 0.02039 = 0.01610 0.00710 0.00437 0.00404 C26 1 0.601976 0.939338 0.607540 11.00000 0.02881 0.01875 = 0.02577 0.01013 0.01086 0.00974 AFIX 43 H26A 2 0.618868 1.024558 0.604522 11.00000 -1.20000 AFIX 0 C27 1 0.549044 0.915017 0.694584 11.00000 0.03507 0.02265 = 0.02774 0.00940 0.01725 0.01509 AFIX 43 H27A 2 0.530290 0.983752 0.750997 11.00000 -1.20000 AFIX 0 C28 1 0.522969 0.790942 0.700406 11.00000 0.02318 0.02352 = 0.02063 0.00886 0.01005 0.00846 C29 1 0.555927 0.693134 0.620294 11.00000 0.02322 0.01628 = 0.02251 0.00743 0.00892 0.00549 AFIX 43 H29A 2 0.542195 0.608951 0.625469 11.00000 -1.20000 AFIX 0 C30 1 0.609138 0.717299 0.532053 11.00000 0.02372 0.01834 = 0.01983 0.00476 0.00898 0.00707 AFIX 43 H30A 2 0.630594 0.649319 0.477167 11.00000 -1.20000 AFIX 0 B1 5 0.703249 0.790603 0.337124 11.00000 0.02110 0.01778 = 0.01717 0.00730 0.00675 0.00412 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_d12333_0m in P-1 REM R1 = 0.0388 for 4367 Fo > 4sig(Fo) and 0.0507 for all 5363 data REM 356 parameters refined using 0 restraints END WGHT 0.0481 0.2871 REM Highest difference peak 0.241, deepest hole -0.248, 1-sigma level 0.047 Q1 1 0.6309 0.7357 0.2854 11.00000 0.05 0.24 Q2 1 0.8426 0.5580 0.3244 11.00000 0.05 0.24 Q3 1 0.3754 0.5369 0.0847 11.00000 0.05 0.22 Q4 1 0.9190 0.9450 0.2383 11.00000 0.05 0.21 Q5 1 0.4528 0.5147 0.1751 11.00000 0.05 0.21 Q6 1 0.4069 0.6543 0.1032 11.00000 0.05 0.20 Q7 1 0.7680 0.7594 0.3559 11.00000 0.05 0.20 Q8 1 0.5789 0.7599 0.6865 11.00000 0.05 0.20 Q9 1 0.7031 0.9521 0.1655 11.00000 0.05 0.20 Q10 1 0.7392 0.9776 0.0849 11.00000 0.05 0.20 Q11 1 0.9661 0.5941 0.3435 11.00000 0.05 0.20 Q12 1 0.9344 0.5029 0.3742 11.00000 0.05 0.20 Q13 1 0.5272 0.9062 0.6164 11.00000 0.05 0.19 Q14 1 0.5086 0.8420 0.6712 11.00000 0.05 0.19 Q15 1 0.6240 0.7242 0.6040 11.00000 0.05 0.18 Q16 1 0.1306 0.3958 -0.0333 11.00000 0.05 0.18 Q17 1 0.5735 0.7630 0.4976 11.00000 0.05 0.18 Q18 1 0.8398 1.0215 0.2005 11.00000 0.05 0.18 Q19 1 1.0181 0.7381 0.4158 11.00000 0.05 0.17 Q20 1 0.7272 0.8351 0.3031 11.00000 0.05 0.17 ; _database_code_depnum_ccdc_archive 'CCDC 949041' ####################################################################### # # 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_d12198 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Hydroxo)(subphthalocyaninato)boron ; _chemical_name_common ; HO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H13 B N6 O' _chemical_formula_sum 'C24 H13 B N6 O' _chemical_formula_weight 412.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 '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 26.2251(13) _cell_length_b 11.7733(7) _cell_length_c 12.0258(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.248(3) _cell_angle_gamma 90.00 _cell_volume 3710.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 147(2) _cell_measurement_reflns_used 7182 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 66.58 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6650 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 147(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker ImuS' _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_measurement_device_type 'Bruker Kappa APEX-DUO CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11749 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 66.58 _reflns_number_total 3179 _reflns_number_gt 2813 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0506P)^2^+2.3513P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3179 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 O1 O 0.04771(4) 0.11707(9) 1.07372(9) 0.0306(3) Uani 1 1 d . . . H1O H 0.0540(9) 0.079(2) 1.135(2) 0.068(7) Uiso 1 1 d . . . N1 N 0.10972(4) 0.00153(10) 0.96998(10) 0.0258(3) Uani 1 1 d . . . N2 N 0.06974(4) 0.00565(11) 0.78938(10) 0.0274(3) Uani 1 1 d . . . N3 N 0.08022(4) 0.17444(10) 0.89552(10) 0.0260(3) Uani 1 1 d . . . N4 N 0.12315(5) 0.34466(11) 0.94910(10) 0.0321(3) Uani 1 1 d . . . N5 N 0.13842(5) 0.17307(10) 1.04889(10) 0.0266(3) Uani 1 1 d . . . N6 N 0.18300(5) 0.00262(11) 1.09263(10) 0.0276(3) Uani 1 1 d . . . C1 C 0.14995(5) -0.05223(13) 1.02293(12) 0.0268(3) Uani 1 1 d . . . C2 C 0.15427(6) -0.16125(13) 0.96809(12) 0.0288(3) Uani 1 1 d . . . C3 C 0.18662(6) -0.25315(14) 0.98819(13) 0.0344(4) Uani 1 1 d . . . H3A H 0.2102 -0.2535 1.0501 0.041 Uiso 1 1 calc R . . C4 C 0.18339(7) -0.34398(14) 0.91537(14) 0.0392(4) Uani 1 1 d . . . H4A H 0.2056 -0.4070 0.9267 0.047 Uiso 1 1 calc R . . C5 C 0.14813(7) -0.34466(13) 0.82569(14) 0.0375(4) Uani 1 1 d . . . H5A H 0.1463 -0.4093 0.7784 0.045 Uiso 1 1 calc R . . C6 C 0.11573(6) -0.25421(13) 0.80350(13) 0.0339(4) Uani 1 1 d . . . H6A H 0.0920 -0.2556 0.7418 0.041 Uiso 1 1 calc R . . C7 C 0.11913(6) -0.16105(13) 0.87466(12) 0.0287(3) Uani 1 1 d . . . C8 C 0.09395(5) -0.05095(13) 0.87352(12) 0.0270(3) Uani 1 1 d . . . C9 C 0.06633(5) 0.11889(13) 0.79944(12) 0.0257(3) Uani 1 1 d . . . C10 C 0.05873(5) 0.20705(13) 0.71534(12) 0.0275(3) Uani 1 1 d . . . C11 C 0.04176(5) 0.20297(14) 0.60379(12) 0.0304(4) Uani 1 1 d . . . H11A H 0.0324 0.1330 0.5694 0.037 Uiso 1 1 calc R . . C12 C 0.03896(6) 0.30326(15) 0.54522(13) 0.0371(4) Uani 1 1 d . . . H12A H 0.0268 0.3024 0.4698 0.045 Uiso 1 1 calc R . . C13 C 0.05361(7) 0.40620(16) 0.59409(15) 0.0435(4) Uani 1 1 d . . . H13A H 0.0516 0.4738 0.5510 0.052 Uiso 1 1 calc R . . C14 C 0.07108(7) 0.41180(15) 0.70489(15) 0.0409(4) Uani 1 1 d . . . H14A H 0.0810 0.4821 0.7379 0.049 Uiso 1 1 calc R . . C15 C 0.07353(6) 0.31152(14) 0.76543(13) 0.0311(4) Uani 1 1 d . . . C16 C 0.09139(6) 0.28600(13) 0.87956(12) 0.0293(3) Uani 1 1 d . . . C17 C 0.14885(6) 0.28397(13) 1.02833(12) 0.0290(3) Uani 1 1 d . . . C18 C 0.19745(6) 0.30716(13) 1.08775(12) 0.0302(3) Uani 1 1 d . . . C19 C 0.22574(6) 0.40616(14) 1.10266(12) 0.0349(4) Uani 1 1 d . . . H19A H 0.2139 0.4764 1.0725 0.042 Uiso 1 1 calc R . . C20 C 0.27192(6) 0.39924(15) 1.16312(12) 0.0373(4) Uani 1 1 d . . . H20A H 0.2915 0.4662 1.1759 0.045 Uiso 1 1 calc R . . C21 C 0.29000(6) 0.29606(15) 1.20534(12) 0.0358(4) Uani 1 1 d . . . H21A H 0.3217 0.2942 1.2462 0.043 Uiso 1 1 calc R . . C22 C 0.26287(6) 0.19631(14) 1.18924(12) 0.0322(4) Uani 1 1 d . . . H22A H 0.2759 0.1259 1.2166 0.039 Uiso 1 1 calc R . . C23 C 0.21570(6) 0.20249(13) 1.13138(12) 0.0289(3) Uani 1 1 d . . . C24 C 0.17849(6) 0.11585(13) 1.09847(11) 0.0274(3) Uani 1 1 d . . . B1 B 0.09023(6) 0.11544(15) 1.00517(13) 0.0266(4) 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 O1 0.0293(6) 0.0353(6) 0.0268(6) 0.0028(5) -0.0043(4) 0.0028(4) N1 0.0243(6) 0.0277(6) 0.0248(6) 0.0011(5) -0.0045(5) -0.0022(5) N2 0.0242(6) 0.0310(7) 0.0265(6) -0.0006(5) -0.0048(5) -0.0031(5) N3 0.0238(6) 0.0280(6) 0.0256(6) 0.0009(5) -0.0066(5) -0.0008(5) N4 0.0346(7) 0.0296(7) 0.0310(7) 0.0006(5) -0.0107(6) -0.0011(6) N5 0.0266(6) 0.0285(7) 0.0238(6) 0.0003(5) -0.0075(5) -0.0002(5) N6 0.0281(6) 0.0310(7) 0.0233(6) 0.0026(5) -0.0039(5) 0.0010(5) C1 0.0264(7) 0.0303(8) 0.0235(7) 0.0039(6) -0.0029(6) 0.0005(6) C2 0.0314(8) 0.0279(8) 0.0271(7) 0.0027(6) 0.0007(6) -0.0018(6) C3 0.0389(9) 0.0336(9) 0.0307(8) 0.0060(7) 0.0004(7) 0.0035(7) C4 0.0506(10) 0.0299(8) 0.0374(9) 0.0060(7) 0.0056(8) 0.0064(7) C5 0.0525(10) 0.0261(8) 0.0342(8) 0.0005(7) 0.0054(8) -0.0035(7) C6 0.0413(9) 0.0307(8) 0.0296(8) 0.0011(6) 0.0000(7) -0.0076(7) C7 0.0305(8) 0.0279(8) 0.0276(7) 0.0027(6) -0.0003(6) -0.0039(6) C8 0.0256(7) 0.0305(8) 0.0246(7) -0.0006(6) -0.0028(6) -0.0052(6) C9 0.0195(7) 0.0324(8) 0.0248(7) -0.0008(6) -0.0045(5) -0.0017(6) C10 0.0186(7) 0.0352(8) 0.0283(7) 0.0027(6) -0.0041(6) -0.0003(6) C11 0.0221(7) 0.0414(9) 0.0274(8) 0.0000(6) -0.0046(6) 0.0021(6) C12 0.0317(8) 0.0508(10) 0.0281(8) 0.0063(7) -0.0077(6) 0.0024(7) C13 0.0437(10) 0.0453(10) 0.0403(9) 0.0161(8) -0.0117(8) -0.0018(8) C14 0.0420(10) 0.0362(9) 0.0431(9) 0.0086(8) -0.0157(8) -0.0056(7) C15 0.0264(8) 0.0347(8) 0.0313(8) 0.0044(6) -0.0091(6) -0.0012(6) C16 0.0287(8) 0.0283(8) 0.0302(8) 0.0015(6) -0.0083(6) 0.0000(6) C17 0.0315(8) 0.0287(8) 0.0261(7) -0.0006(6) -0.0076(6) -0.0020(6) C18 0.0327(8) 0.0352(8) 0.0221(7) -0.0003(6) -0.0064(6) -0.0043(7) C19 0.0432(9) 0.0366(9) 0.0245(7) 0.0011(6) -0.0068(7) -0.0092(7) C20 0.0384(9) 0.0475(10) 0.0256(8) -0.0026(7) -0.0030(7) -0.0167(8) C21 0.0288(8) 0.0540(11) 0.0241(7) -0.0033(7) -0.0064(6) -0.0076(7) C22 0.0292(8) 0.0432(9) 0.0237(7) -0.0008(6) -0.0058(6) -0.0008(7) C23 0.0289(8) 0.0359(8) 0.0216(7) -0.0013(6) -0.0051(6) -0.0028(6) C24 0.0264(7) 0.0338(8) 0.0214(7) 0.0019(6) -0.0057(6) 0.0000(6) B1 0.0262(8) 0.0281(9) 0.0249(8) 0.0004(7) -0.0073(7) -0.0003(7) _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 O1 B1 1.413(2) . ? O1 H1O 0.88(3) . ? N1 C8 1.3642(18) . ? N1 C1 1.3661(18) . ? N1 B1 1.502(2) . ? N2 C9 1.342(2) . ? N2 C8 1.3493(19) . ? N3 C16 1.361(2) . ? N3 C9 1.3648(18) . ? N3 B1 1.504(2) . ? N4 C16 1.3473(19) . ? N4 C17 1.3499(19) . ? N5 C17 1.359(2) . ? N5 C24 1.3656(19) . ? N5 B1 1.511(2) . ? N6 C24 1.340(2) . ? N6 C1 1.3468(19) . ? C1 C2 1.450(2) . ? C2 C3 1.390(2) . ? C2 C7 1.425(2) . ? C3 C4 1.383(2) . ? C3 H3A 0.9500 . ? C4 C5 1.393(2) . ? C4 H4A 0.9500 . ? C5 C6 1.382(2) . ? C5 H5A 0.9500 . ? C6 C7 1.392(2) . ? C6 H6A 0.9500 . ? C7 C8 1.454(2) . ? C9 C10 1.457(2) . ? C10 C11 1.398(2) . ? C10 C15 1.417(2) . ? C11 C12 1.375(2) . ? C11 H11A 0.9500 . ? C12 C13 1.394(3) . ? C12 H12A 0.9500 . ? C13 C14 1.393(2) . ? C13 H13A 0.9500 . ? C14 C15 1.387(2) . ? C14 H14A 0.9500 . ? C15 C16 1.464(2) . ? C17 C18 1.462(2) . ? C18 C19 1.389(2) . ? C18 C23 1.415(2) . ? C19 C20 1.390(2) . ? C19 H19A 0.9500 . ? C20 C21 1.393(3) . ? C20 H20A 0.9500 . ? C21 C22 1.383(2) . ? C21 H21A 0.9500 . ? C22 C23 1.397(2) . ? C22 H22A 0.9500 . ? C23 C24 1.456(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag B1 O1 H1O 111.2(16) . . ? C8 N1 C1 112.92(13) . . ? C8 N1 B1 123.28(12) . . ? C1 N1 B1 123.20(12) . . ? C9 N2 C8 117.01(12) . . ? C16 N3 C9 113.26(12) . . ? C16 N3 B1 122.56(12) . . ? C9 N3 B1 123.53(13) . . ? C16 N4 C17 116.49(13) . . ? C17 N5 C24 113.36(12) . . ? C17 N5 B1 122.68(12) . . ? C24 N5 B1 123.33(13) . . ? C24 N6 C1 116.97(12) . . ? N6 C1 N1 122.30(13) . . ? N6 C1 C2 130.37(13) . . ? N1 C1 C2 105.72(12) . . ? C3 C2 C7 120.65(14) . . ? C3 C2 C1 131.92(14) . . ? C7 C2 C1 107.31(13) . . ? C4 C3 C2 118.04(15) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 121.14(16) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C6 C5 C4 121.98(15) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C5 C6 C7 117.69(15) . . ? C5 C6 H6A 121.2 . . ? C7 C6 H6A 121.2 . . ? C6 C7 C2 120.48(14) . . ? C6 C7 C8 132.72(14) . . ? C2 C7 C8 106.76(13) . . ? N2 C8 N1 122.14(14) . . ? N2 C8 C7 130.34(13) . . ? N1 C8 C7 105.85(12) . . ? N2 C9 N3 122.40(13) . . ? N2 C9 C10 130.75(13) . . ? N3 C9 C10 105.72(13) . . ? C11 C10 C15 120.63(14) . . ? C11 C10 C9 132.17(14) . . ? C15 C10 C9 107.19(12) . . ? C12 C11 C10 118.08(15) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C11 C12 C13 121.47(14) . . ? C11 C12 H12A 119.3 . . ? C13 C12 H12A 119.3 . . ? C14 C13 C12 121.26(16) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C15 C14 C13 117.93(16) . . ? C15 C14 H14A 121.0 . . ? C13 C14 H14A 121.0 . . ? C14 C15 C10 120.62(14) . . ? C14 C15 C16 132.32(15) . . ? C10 C15 C16 107.02(13) . . ? N4 C16 N3 122.57(13) . . ? N4 C16 C15 130.09(14) . . ? N3 C16 C15 105.52(13) . . ? N4 C17 N5 122.59(13) . . ? N4 C17 C18 130.36(14) . . ? N5 C17 C18 105.57(13) . . ? C19 C18 C23 120.75(14) . . ? C19 C18 C17 132.11(15) . . ? C23 C18 C17 107.11(13) . . ? C18 C19 C20 117.92(16) . . ? C18 C19 H19A 121.0 . . ? C20 C19 H19A 121.0 . . ? C19 C20 C21 121.26(15) . . ? C19 C20 H20A 119.4 . . ? C21 C20 H20A 119.4 . . ? C22 C21 C20 121.59(14) . . ? C22 C21 H21A 119.2 . . ? C20 C21 H21A 119.2 . . ? C21 C22 C23 117.78(15) . . ? C21 C22 H22A 121.1 . . ? C23 C22 H22A 121.1 . . ? C22 C23 C18 120.66(14) . . ? C22 C23 C24 132.05(15) . . ? C18 C23 C24 107.22(13) . . ? N6 C24 N5 122.39(13) . . ? N6 C24 C23 130.67(14) . . ? N5 C24 C23 105.62(13) . . ? O1 B1 N1 117.50(13) . . ? O1 B1 N3 113.00(12) . . ? N1 B1 N3 102.41(12) . . ? O1 B1 N5 117.35(13) . . ? N1 B1 N5 102.10(12) . . ? N3 B1 N5 102.27(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 N6 C1 N1 -7.6(2) . . . . ? C24 N6 C1 C2 155.81(15) . . . . ? C8 N1 C1 N6 154.83(13) . . . . ? B1 N1 C1 N6 -16.5(2) . . . . ? C8 N1 C1 C2 -12.10(16) . . . . ? B1 N1 C1 C2 176.56(13) . . . . ? N6 C1 C2 C3 17.3(3) . . . . ? N1 C1 C2 C3 -177.28(16) . . . . ? N6 C1 C2 C7 -158.72(15) . . . . ? N1 C1 C2 C7 6.74(16) . . . . ? C7 C2 C3 C4 -0.3(2) . . . . ? C1 C2 C3 C4 -175.87(15) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C5 C6 C7 C2 -1.2(2) . . . . ? C5 C6 C7 C8 175.89(16) . . . . ? C3 C2 C7 C6 1.6(2) . . . . ? C1 C2 C7 C6 178.13(14) . . . . ? C3 C2 C7 C8 -176.19(14) . . . . ? C1 C2 C7 C8 0.33(16) . . . . ? C9 N2 C8 N1 6.7(2) . . . . ? C9 N2 C8 C7 -156.41(15) . . . . ? C1 N1 C8 N2 -154.37(13) . . . . ? B1 N1 C8 N2 17.0(2) . . . . ? C1 N1 C8 C7 12.32(16) . . . . ? B1 N1 C8 C7 -176.35(13) . . . . ? C6 C7 C8 N2 -19.5(3) . . . . ? C2 C7 C8 N2 157.89(15) . . . . ? C6 C7 C8 N1 175.28(16) . . . . ? C2 C7 C8 N1 -7.29(16) . . . . ? C8 N2 C9 N3 -8.6(2) . . . . ? C8 N2 C9 C10 157.42(14) . . . . ? C16 N3 C9 N2 157.95(14) . . . . ? B1 N3 C9 N2 -13.0(2) . . . . ? C16 N3 C9 C10 -11.09(16) . . . . ? B1 N3 C9 C10 177.95(13) . . . . ? N2 C9 C10 C11 16.3(3) . . . . ? N3 C9 C10 C11 -175.96(15) . . . . ? N2 C9 C10 C15 -162.33(15) . . . . ? N3 C9 C10 C15 5.44(15) . . . . ? C15 C10 C11 C12 -1.2(2) . . . . ? C9 C10 C11 C12 -179.67(15) . . . . ? C10 C11 C12 C13 1.4(2) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C10 0.1(3) . . . . ? C13 C14 C15 C16 177.35(17) . . . . ? C11 C10 C15 C14 0.5(2) . . . . ? C9 C10 C15 C14 179.29(15) . . . . ? C11 C10 C15 C16 -177.39(13) . . . . ? C9 C10 C15 C16 1.41(16) . . . . ? C17 N4 C16 N3 8.3(2) . . . . ? C17 N4 C16 C15 -154.03(16) . . . . ? C9 N3 C16 N4 -154.12(14) . . . . ? B1 N3 C16 N4 16.9(2) . . . . ? C9 N3 C16 C15 11.94(17) . . . . ? B1 N3 C16 C15 -177.00(13) . . . . ? C14 C15 C16 N4 -20.7(3) . . . . ? C10 C15 C16 N4 156.85(16) . . . . ? C14 C15 C16 N3 174.72(17) . . . . ? C10 C15 C16 N3 -7.75(17) . . . . ? C16 N4 C17 N5 -9.4(2) . . . . ? C16 N4 C17 C18 154.56(16) . . . . ? C24 N5 C17 N4 156.66(14) . . . . ? B1 N5 C17 N4 -14.5(2) . . . . ? C24 N5 C17 C18 -10.75(17) . . . . ? B1 N5 C17 C18 178.06(13) . . . . ? N4 C17 C18 C19 18.0(3) . . . . ? N5 C17 C18 C19 -176.00(16) . . . . ? N4 C17 C18 C23 -159.98(16) . . . . ? N5 C17 C18 C23 6.08(17) . . . . ? C23 C18 C19 C20 -1.0(2) . . . . ? C17 C18 C19 C20 -178.72(16) . . . . ? C18 C19 C20 C21 1.5(2) . . . . ? C19 C20 C21 C22 -0.1(2) . . . . ? C20 C21 C22 C23 -1.7(2) . . . . ? C21 C22 C23 C18 2.1(2) . . . . ? C21 C22 C23 C24 178.61(15) . . . . ? C19 C18 C23 C22 -0.8(2) . . . . ? C17 C18 C23 C22 177.43(14) . . . . ? C19 C18 C23 C24 -178.05(14) . . . . ? C17 C18 C23 C24 0.16(17) . . . . ? C1 N6 C24 N5 8.8(2) . . . . ? C1 N6 C24 C23 -156.05(15) . . . . ? C17 N5 C24 N6 -157.27(14) . . . . ? B1 N5 C24 N6 13.9(2) . . . . ? C17 N5 C24 C23 10.87(17) . . . . ? B1 N5 C24 C23 -178.01(13) . . . . ? C22 C23 C24 N6 -16.4(3) . . . . ? C18 C23 C24 N6 160.46(15) . . . . ? C22 C23 C24 N5 176.85(16) . . . . ? C18 C23 C24 N5 -6.30(16) . . . . ? C8 N1 B1 O1 92.25(17) . . . . ? C1 N1 B1 O1 -97.29(16) . . . . ? C8 N1 B1 N3 -32.20(17) . . . . ? C1 N1 B1 N3 138.25(13) . . . . ? C8 N1 B1 N5 -137.85(13) . . . . ? C1 N1 B1 N5 32.61(17) . . . . ? C16 N3 B1 O1 92.81(17) . . . . ? C9 N3 B1 O1 -97.05(16) . . . . ? C16 N3 B1 N1 -139.81(13) . . . . ? C9 N3 B1 N1 30.33(17) . . . . ? C16 N3 B1 N5 -34.29(18) . . . . ? C9 N3 B1 N5 135.85(13) . . . . ? C17 N5 B1 O1 -91.09(17) . . . . ? C24 N5 B1 O1 98.60(17) . . . . ? C17 N5 B1 N1 138.92(13) . . . . ? C24 N5 B1 N1 -31.39(17) . . . . ? C17 N5 B1 N3 33.16(18) . . . . ? C24 N5 B1 N3 -137.15(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N2 0.88(3) 2.13(3) 3.0049(16) 177(2) 6_556 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.451 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.048 _iucr_refine_instructions_details ; TITL cu_d12198_0m in C2/c CELL 1.54178 26.2251 11.7733 12.0258 90.000 92.248 90.000 ZERR 8.00 0.0013 0.0007 0.0006 0.000 0.003 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H N O B UNIT 192 104 48 8 8 TEMP -126.150 SIZE 0.060 0.070 0.110 ACTA OMIT 2 0 0 L.S. 4 FMAP 2 PLAN 20 EQIV $1 x, -y, z+1/2 HTAB O1 N2_$1 BOND $H CONF WGHT 0.0506 2.3513 FVAR 0.06224 O1 4 0.047710 0.117070 1.073724 11.00000 0.02932 0.03534 = 0.02680 0.00281 -0.00434 0.00284 H1O 2 0.054139 0.078966 1.135421 11.00000 0.06838 N1 3 0.109721 0.001525 0.969987 11.00000 0.02434 0.02776 = 0.02490 0.00114 -0.00444 -0.00216 N2 3 0.069742 0.005655 0.789378 11.00000 0.02423 0.03111 = 0.02650 -0.00061 -0.00481 -0.00310 N3 3 0.080221 0.174441 0.895522 11.00000 0.02382 0.02809 = 0.02563 0.00095 -0.00660 -0.00083 N4 3 0.123145 0.344665 0.949100 11.00000 0.03465 0.02964 = 0.03109 0.00057 -0.01075 -0.00109 N5 3 0.138416 0.173060 1.048891 11.00000 0.02669 0.02860 = 0.02384 0.00029 -0.00745 -0.00024 N6 3 0.183000 0.002621 1.092631 11.00000 0.02812 0.03102 = 0.02340 0.00259 -0.00385 0.00095 C1 1 0.149947 -0.052218 1.022930 11.00000 0.02641 0.03037 = 0.02357 0.00388 -0.00283 0.00049 C2 1 0.154269 -0.161246 0.968091 11.00000 0.03143 0.02798 = 0.02715 0.00272 0.00063 -0.00183 C3 1 0.186617 -0.253148 0.988185 11.00000 0.03892 0.03365 = 0.03079 0.00606 0.00041 0.00350 AFIX 43 H3A 2 0.210242 -0.253528 1.050123 11.00000 -1.20000 AFIX 0 C4 1 0.183391 -0.343988 0.915366 11.00000 0.05059 0.02996 = 0.03745 0.00603 0.00562 0.00634 AFIX 43 H4A 2 0.205607 -0.407021 0.926697 11.00000 -1.20000 AFIX 0 C5 1 0.148130 -0.344662 0.825688 11.00000 0.05251 0.02618 = 0.03422 0.00049 0.00546 -0.00350 AFIX 43 H5A 2 0.146300 -0.409252 0.778350 11.00000 -1.20000 AFIX 0 C6 1 0.115732 -0.254214 0.803501 11.00000 0.04139 0.03076 = 0.02961 0.00104 -0.00002 -0.00756 AFIX 43 H6A 2 0.091968 -0.255569 0.741827 11.00000 -1.20000 AFIX 0 C7 1 0.119127 -0.161048 0.874662 11.00000 0.03053 0.02796 = 0.02764 0.00271 -0.00030 -0.00392 C8 1 0.093943 -0.050947 0.873513 11.00000 0.02563 0.03048 = 0.02462 -0.00063 -0.00277 -0.00520 C9 1 0.066326 0.118892 0.799443 11.00000 0.01956 0.03245 = 0.02484 -0.00074 -0.00445 -0.00174 C10 1 0.058735 0.207042 0.715337 11.00000 0.01859 0.03525 = 0.02840 0.00269 -0.00416 -0.00030 C11 1 0.041753 0.202975 0.603775 11.00000 0.02213 0.04152 = 0.02741 -0.00002 -0.00464 0.00209 AFIX 43 H11A 2 0.032408 0.132957 0.569403 11.00000 -1.20000 AFIX 0 C12 1 0.038961 0.303251 0.545201 11.00000 0.03165 0.05090 = 0.02821 0.00625 -0.00768 0.00233 AFIX 43 H12A 2 0.026780 0.302366 0.469760 11.00000 -1.20000 AFIX 0 C13 1 0.053613 0.406203 0.594086 11.00000 0.04383 0.04531 = 0.04037 0.01604 -0.01174 -0.00183 AFIX 43 H13A 2 0.051654 0.473819 0.551019 11.00000 -1.20000 AFIX 0 C14 1 0.071072 0.411805 0.704887 11.00000 0.04206 0.03629 = 0.04316 0.00858 -0.01564 -0.00564 AFIX 43 H14A 2 0.080981 0.482108 0.737940 11.00000 -1.20000 AFIX 0 C15 1 0.073532 0.311522 0.765431 11.00000 0.02649 0.03482 = 0.03132 0.00438 -0.00912 -0.00114 C16 1 0.091389 0.286008 0.879567 11.00000 0.02876 0.02834 = 0.03020 0.00150 -0.00834 -0.00003 C17 1 0.148845 0.283974 1.028327 11.00000 0.03144 0.02880 = 0.02613 -0.00063 -0.00759 -0.00197 C18 1 0.197447 0.307164 1.087746 11.00000 0.03276 0.03527 = 0.02218 -0.00033 -0.00643 -0.00428 C19 1 0.225737 0.406168 1.102654 11.00000 0.04320 0.03659 = 0.02450 0.00110 -0.00676 -0.00923 AFIX 43 H19A 2 0.213897 0.476378 1.072485 11.00000 -1.20000 AFIX 0 C20 1 0.271919 0.399240 1.163116 11.00000 0.03840 0.04759 = 0.02569 -0.00253 -0.00293 -0.01669 AFIX 43 H20A 2 0.291514 0.466179 1.175873 11.00000 -1.20000 AFIX 0 C21 1 0.290006 0.296062 1.205339 11.00000 0.02882 0.05410 = 0.02415 -0.00329 -0.00642 -0.00759 AFIX 43 H21A 2 0.321747 0.294163 1.246177 11.00000 -1.20000 AFIX 0 C22 1 0.262873 0.196316 1.189245 11.00000 0.02921 0.04327 = 0.02380 -0.00083 -0.00585 -0.00078 AFIX 43 H22A 2 0.275871 0.125928 1.216618 11.00000 -1.20000 AFIX 0 C23 1 0.215696 0.202496 1.131378 11.00000 0.02890 0.03594 = 0.02167 -0.00133 -0.00512 -0.00277 C24 1 0.178496 0.115848 1.098474 11.00000 0.02642 0.03389 = 0.02146 0.00191 -0.00564 -0.00003 B1 5 0.090227 0.115451 1.005167 11.00000 0.02623 0.02819 = 0.02496 0.00041 -0.00731 -0.00031 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_d12198_0m in C2/c REM R1 = 0.0388 for 2813 Fo > 4sig(Fo) and 0.0441 for all 3179 data REM 293 parameters refined using 0 restraints END REM Highest difference peak 0.451, deepest hole -0.241, 1-sigma level 0.048 Q1 1 0.0000 -0.2638 0.7500 10.50000 0.05 0.45 Q2 1 0.0377 -0.3376 0.6396 11.00000 0.05 0.26 Q3 1 0.1498 0.3406 0.8932 11.00000 0.05 0.15 Q4 1 0.0928 0.4021 0.6401 11.00000 0.05 0.15 Q5 1 0.0349 0.1847 1.1606 11.00000 0.05 0.13 Q6 1 0.1105 -0.3380 0.8556 11.00000 0.05 0.13 Q7 1 0.0000 0.6158 0.7500 10.50000 0.05 0.13 Q8 1 0.0790 0.3117 0.8189 11.00000 0.05 0.13 Q9 1 0.2313 -0.3958 0.9249 11.00000 0.05 0.13 Q10 1 0.2777 0.5021 1.2041 11.00000 0.05 0.12 Q11 1 0.0798 0.1472 0.9517 11.00000 0.05 0.12 Q12 1 0.0708 0.3515 0.5471 11.00000 0.05 0.12 Q13 1 0.0898 -0.0198 0.7314 11.00000 0.05 0.12 Q14 1 0.1017 0.0567 0.9769 11.00000 0.05 0.12 Q15 1 0.1101 0.4780 0.7246 11.00000 0.05 0.11 Q16 1 0.1686 0.1706 0.9653 11.00000 0.05 0.11 Q17 1 0.1268 0.2985 0.7096 11.00000 0.05 0.11 Q18 1 0.1480 -0.1493 0.9038 11.00000 0.05 0.10 Q19 1 0.0000 0.0000 0.5000 10.50000 0.05 0.10 Q20 1 0.0000 0.5248 0.7500 10.50000 0.05 0.10 ; _database_code_depnum_ccdc_archive 'CCDC 949042' ####################################################################### # # 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_k1164a _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Hydroxyphenolato)(subphthalocyaninato)boron ; _chemical_name_common ; o-HOPhO-BsubPc ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H17 B N6 O2' _chemical_formula_sum 'C30 H17 B N6 O2' _chemical_formula_weight 504.31 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' _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 23.4583(4) _cell_length_b 11.7386(2) _cell_length_c 19.4923(5) _cell_angle_alpha 90.00 _cell_angle_beta 120.188(1) _cell_angle_gamma 90.00 _cell_volume 4639.60(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18756 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.0 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6696 _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 Kappa ApexII' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18756 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.01 _reflns_number_total 4990 _reflns_number_gt 3896 _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^)+(0.0465P)^2^+2.1213P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4990 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 O1 O 0.16046(5) 0.55298(8) 0.38704(5) 0.0189(2) Uani 1 1 d . . . O2 O 0.28240(5) 0.44760(10) 0.45550(7) 0.0350(3) Uani 1 1 d . . . H1O H 0.2760(10) 0.525(2) 0.4579(13) 0.064(7) Uiso 1 1 d . . . N1 N 0.09870(5) 0.70397(9) 0.40655(6) 0.0166(2) Uani 1 1 d . . . N2 N -0.00854(5) 0.61939(10) 0.34163(6) 0.0189(3) Uani 1 1 d . . . N3 N 0.08397(5) 0.51749(10) 0.43845(6) 0.0172(2) Uani 1 1 d . . . N4 N 0.15602(6) 0.44393(10) 0.56672(7) 0.0195(3) Uani 1 1 d . . . N5 N 0.18317(5) 0.61352(9) 0.52146(6) 0.0164(2) Uani 1 1 d . . . N6 N 0.18322(5) 0.81509(10) 0.50874(6) 0.0168(2) Uani 1 1 d . . . C1 C 0.12616(7) 0.80685(11) 0.43916(8) 0.0167(3) Uani 1 1 d . . . C2 C 0.07437(7) 0.89153(12) 0.39641(8) 0.0177(3) Uani 1 1 d . . . C3 C 0.07255(7) 1.00938(12) 0.40257(8) 0.0208(3) Uani 1 1 d . . . H3A H 0.1114 1.0513 0.4363 0.025 Uiso 1 1 calc R . . C4 C 0.01243(7) 1.06369(13) 0.35805(8) 0.0239(3) Uani 1 1 d . . . H4A H 0.0103 1.1442 0.3610 0.029 Uiso 1 1 calc R . . C5 C -0.04523(7) 1.00284(13) 0.30894(9) 0.0247(3) Uani 1 1 d . . . H5A H -0.0857 1.0428 0.2797 0.030 Uiso 1 1 calc R . . C6 C -0.04453(7) 0.88574(13) 0.30207(8) 0.0220(3) Uani 1 1 d . . . H6A H -0.0838 0.8447 0.2686 0.026 Uiso 1 1 calc R . . C7 C 0.01567(7) 0.82979(12) 0.34585(8) 0.0183(3) Uani 1 1 d . . . C8 C 0.03165(7) 0.70950(12) 0.35739(8) 0.0180(3) Uani 1 1 d . . . C9 C 0.01809(7) 0.52598(12) 0.38601(8) 0.0182(3) Uani 1 1 d . . . C10 C -0.01176(7) 0.42860(12) 0.40265(8) 0.0196(3) Uani 1 1 d . . . C11 C -0.07598(7) 0.38689(13) 0.36519(9) 0.0230(3) Uani 1 1 d . . . H11A H -0.1105 0.4241 0.3201 0.028 Uiso 1 1 calc R . . C12 C -0.08798(8) 0.28904(13) 0.39589(9) 0.0267(3) Uani 1 1 d . . . H12A H -0.1310 0.2569 0.3698 0.032 Uiso 1 1 calc R . . C13 C -0.03828(8) 0.23671(13) 0.46425(9) 0.0267(3) Uani 1 1 d . . . H13A H -0.0483 0.1703 0.4839 0.032 Uiso 1 1 calc R . . C14 C 0.02520(7) 0.27941(12) 0.50388(9) 0.0236(3) Uani 1 1 d . . . H14A H 0.0584 0.2448 0.5513 0.028 Uiso 1 1 calc R . . C15 C 0.03914(7) 0.37450(12) 0.47230(8) 0.0200(3) Uani 1 1 d . . . C16 C 0.09935(7) 0.43937(11) 0.49704(8) 0.0179(3) Uani 1 1 d . . . C17 C 0.19434(7) 0.53606(12) 0.57959(8) 0.0179(3) Uani 1 1 d . . . C18 C 0.24081(7) 0.59015(12) 0.65429(8) 0.0186(3) Uani 1 1 d . . . C19 C 0.26741(7) 0.55370(13) 0.73274(8) 0.0222(3) Uani 1 1 d . . . H19A H 0.2621 0.4773 0.7446 0.027 Uiso 1 1 calc R . . C20 C 0.30177(7) 0.63213(13) 0.79253(8) 0.0253(3) Uani 1 1 d . . . H20A H 0.3202 0.6091 0.8463 0.030 Uiso 1 1 calc R . . C21 C 0.30996(7) 0.74490(13) 0.77546(8) 0.0237(3) Uani 1 1 d . . . H21A H 0.3335 0.7969 0.8179 0.028 Uiso 1 1 calc R . . C22 C 0.28444(7) 0.78206(13) 0.69799(8) 0.0203(3) Uani 1 1 d . . . H22A H 0.2906 0.8584 0.6869 0.024 Uiso 1 1 calc R . . C23 C 0.24950(6) 0.70425(12) 0.63680(8) 0.0177(3) Uani 1 1 d . . . C24 C 0.20826(6) 0.71866(11) 0.55126(8) 0.0166(3) Uani 1 1 d . . . C25 C 0.16408(7) 0.43758(12) 0.37600(8) 0.0184(3) Uani 1 1 d . . . C26 C 0.22586(7) 0.38660(12) 0.41151(8) 0.0228(3) Uani 1 1 d . . . C27 C 0.23127(8) 0.27062(13) 0.40185(10) 0.0304(4) Uani 1 1 d . . . H27A H 0.2735 0.2356 0.4264 0.036 Uiso 1 1 calc R . . C28 C 0.17538(8) 0.20618(13) 0.35669(10) 0.0313(4) Uani 1 1 d . . . H28A H 0.1792 0.1265 0.3513 0.038 Uiso 1 1 calc R . . C29 C 0.11398(8) 0.25716(14) 0.31929(9) 0.0304(4) Uani 1 1 d . . . H29A H 0.0757 0.2130 0.2873 0.036 Uiso 1 1 calc R . . C30 C 0.10845(7) 0.37280(13) 0.32852(8) 0.0246(3) Uani 1 1 d . . . H30A H 0.0663 0.4080 0.3022 0.029 Uiso 1 1 calc R . . B1 B 0.13370(7) 0.59283(13) 0.43534(9) 0.0170(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0221(5) 0.0149(5) 0.0226(5) -0.0008(4) 0.0135(4) 0.0000(4) O2 0.0189(6) 0.0232(6) 0.0488(7) -0.0074(5) 0.0064(5) -0.0007(5) N1 0.0145(6) 0.0170(6) 0.0173(6) -0.0002(5) 0.0073(5) -0.0003(5) N2 0.0180(6) 0.0197(6) 0.0178(6) -0.0014(5) 0.0080(5) -0.0013(5) N3 0.0173(6) 0.0167(6) 0.0173(6) -0.0016(5) 0.0085(5) -0.0004(5) N4 0.0206(6) 0.0159(6) 0.0213(6) 0.0002(5) 0.0101(5) 0.0015(5) N5 0.0139(6) 0.0160(6) 0.0187(6) 0.0008(4) 0.0078(5) 0.0012(5) N6 0.0151(6) 0.0174(6) 0.0183(6) 0.0007(5) 0.0088(5) 0.0000(5) C1 0.0194(7) 0.0154(7) 0.0185(7) 0.0004(5) 0.0119(6) -0.0005(6) C2 0.0178(7) 0.0207(7) 0.0159(7) 0.0026(5) 0.0094(6) 0.0017(6) C3 0.0213(7) 0.0205(7) 0.0197(7) 0.0023(6) 0.0097(6) 0.0005(6) C4 0.0274(8) 0.0180(7) 0.0259(8) 0.0041(6) 0.0132(7) 0.0043(6) C5 0.0201(8) 0.0270(8) 0.0262(8) 0.0081(6) 0.0110(6) 0.0075(6) C6 0.0181(7) 0.0264(8) 0.0197(7) 0.0047(6) 0.0083(6) 0.0011(6) C7 0.0202(7) 0.0201(7) 0.0160(6) 0.0026(5) 0.0102(6) 0.0008(6) C8 0.0163(7) 0.0222(7) 0.0141(6) 0.0000(5) 0.0066(6) 0.0012(6) C9 0.0171(7) 0.0205(7) 0.0184(7) -0.0045(5) 0.0099(6) -0.0011(6) C10 0.0213(7) 0.0189(7) 0.0226(7) -0.0041(6) 0.0140(6) -0.0010(6) C11 0.0201(7) 0.0248(8) 0.0264(8) -0.0046(6) 0.0134(6) -0.0019(6) C12 0.0245(8) 0.0283(8) 0.0348(9) -0.0092(7) 0.0205(7) -0.0074(7) C13 0.0359(9) 0.0229(8) 0.0328(8) -0.0048(6) 0.0257(7) -0.0067(7) C14 0.0294(8) 0.0207(7) 0.0243(7) -0.0014(6) 0.0161(7) -0.0025(6) C15 0.0230(7) 0.0181(7) 0.0221(7) -0.0051(6) 0.0139(6) -0.0020(6) C16 0.0221(7) 0.0141(7) 0.0208(7) -0.0011(5) 0.0133(6) 0.0010(6) C17 0.0165(7) 0.0175(7) 0.0195(7) 0.0015(5) 0.0089(6) 0.0037(6) C18 0.0142(7) 0.0200(7) 0.0210(7) -0.0002(6) 0.0084(6) 0.0026(6) C19 0.0193(7) 0.0234(8) 0.0227(7) 0.0052(6) 0.0097(6) 0.0030(6) C20 0.0218(8) 0.0331(9) 0.0187(7) 0.0028(6) 0.0085(6) 0.0023(7) C21 0.0202(7) 0.0271(8) 0.0203(7) -0.0037(6) 0.0075(6) -0.0005(6) C22 0.0160(7) 0.0220(7) 0.0223(7) -0.0011(6) 0.0092(6) 0.0004(6) C23 0.0128(6) 0.0202(7) 0.0198(7) 0.0015(5) 0.0078(6) 0.0033(6) C24 0.0142(7) 0.0171(7) 0.0198(7) -0.0005(5) 0.0095(6) 0.0003(5) C25 0.0230(7) 0.0167(7) 0.0189(7) -0.0021(5) 0.0132(6) -0.0004(6) C26 0.0214(8) 0.0207(7) 0.0243(7) -0.0023(6) 0.0100(6) -0.0022(6) C27 0.0303(9) 0.0221(8) 0.0399(9) 0.0002(7) 0.0185(8) 0.0045(7) C28 0.0429(10) 0.0175(8) 0.0403(9) -0.0058(7) 0.0259(8) -0.0035(7) C29 0.0332(9) 0.0270(8) 0.0338(9) -0.0126(7) 0.0190(7) -0.0117(7) C30 0.0215(8) 0.0286(8) 0.0227(7) -0.0051(6) 0.0104(6) -0.0023(6) B1 0.0150(8) 0.0163(8) 0.0186(8) -0.0011(6) 0.0076(6) -0.0003(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C25 1.3809(16) . ? O1 B1 1.4468(18) . ? O2 C26 1.3651(18) . ? O2 H1O 0.93(2) . ? N1 C1 1.3658(17) . ? N1 C8 1.3713(17) . ? N1 B1 1.4925(19) . ? N2 C9 1.3406(18) . ? N2 C8 1.3456(18) . ? N3 C9 1.3619(17) . ? N3 C16 1.3642(17) . ? N3 B1 1.4892(19) . ? N4 C16 1.3413(18) . ? N4 C17 1.3468(18) . ? N5 C24 1.3651(17) . ? N5 C17 1.3714(17) . ? N5 B1 1.5049(19) . ? N6 C1 1.3472(17) . ? N6 C24 1.3505(17) . ? C1 C2 1.4630(19) . ? C2 C3 1.391(2) . ? C2 C7 1.424(2) . ? C3 C4 1.385(2) . ? C3 H3A 0.9500 . ? C4 C5 1.398(2) . ? C4 H4A 0.9500 . ? C5 C6 1.382(2) . ? C5 H5A 0.9500 . ? C6 C7 1.394(2) . ? C6 H6A 0.9500 . ? C7 C8 1.4492(19) . ? C9 C10 1.460(2) . ? C10 C11 1.392(2) . ? C10 C15 1.429(2) . ? C11 C12 1.388(2) . ? C11 H11A 0.9500 . ? C12 C13 1.396(2) . ? C12 H12A 0.9500 . ? C13 C14 1.381(2) . ? C13 H13A 0.9500 . ? C14 C15 1.391(2) . ? C14 H14A 0.9500 . ? C15 C16 1.457(2) . ? C17 C18 1.4544(19) . ? C18 C19 1.3969(19) . ? C18 C23 1.4218(19) . ? C19 C20 1.382(2) . ? C19 H19A 0.9500 . ? C20 C21 1.402(2) . ? C20 H20A 0.9500 . ? C21 C22 1.386(2) . ? C21 H21A 0.9500 . ? C22 C23 1.3947(19) . ? C22 H22A 0.9500 . ? C23 C24 1.4568(18) . ? C25 C30 1.387(2) . ? C25 C26 1.389(2) . ? C26 C27 1.389(2) . ? C27 C28 1.380(2) . ? C27 H27A 0.9500 . ? C28 C29 1.381(2) . ? C28 H28A 0.9500 . ? C29 C30 1.384(2) . ? 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 119.96(11) . . ? C26 O2 H1O 114.5(13) . . ? C1 N1 C8 112.97(11) . . ? C1 N1 B1 123.80(11) . . ? C8 N1 B1 121.66(11) . . ? C9 N2 C8 116.75(11) . . ? C9 N3 C16 113.59(12) . . ? C9 N3 B1 122.85(12) . . ? C16 N3 B1 123.40(12) . . ? C16 N4 C17 116.71(12) . . ? C24 N5 C17 112.67(11) . . ? C24 N5 B1 123.11(11) . . ? C17 N5 B1 122.31(11) . . ? C1 N6 C24 117.58(11) . . ? N6 C1 N1 121.96(12) . . ? N6 C1 C2 130.15(12) . . ? N1 C1 C2 105.87(11) . . ? C3 C2 C7 120.32(13) . . ? C3 C2 C1 132.79(13) . . ? C7 C2 C1 106.58(12) . . ? C4 C3 C2 118.00(13) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 121.58(14) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 C4 121.35(13) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C7 117.85(13) . . ? C5 C6 H6A 121.1 . . ? C7 C6 H6A 121.1 . . ? C6 C7 C2 120.89(13) . . ? C6 C7 C8 131.12(13) . . ? C2 C7 C8 107.69(12) . . ? N2 C8 N1 123.23(12) . . ? N2 C8 C7 129.32(12) . . ? N1 C8 C7 105.71(11) . . ? N2 C9 N3 121.93(12) . . ? N2 C9 C10 131.60(12) . . ? N3 C9 C10 105.43(12) . . ? C11 C10 C15 120.61(13) . . ? C11 C10 C9 132.28(13) . . ? C15 C10 C9 107.11(12) . . ? C12 C11 C10 117.76(14) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C13 121.50(14) . . ? C11 C12 H12A 119.3 . . ? C13 C12 H12A 119.3 . . ? C14 C13 C12 121.47(14) . . ? C14 C13 H13A 119.3 . . ? C12 C13 H13A 119.3 . . ? C13 C14 C15 118.09(14) . . ? C13 C14 H14A 121.0 . . ? C15 C14 H14A 121.0 . . ? C14 C15 C10 120.47(13) . . ? C14 C15 C16 132.65(13) . . ? C10 C15 C16 106.87(12) . . ? N4 C16 N3 122.08(12) . . ? N4 C16 C15 131.18(13) . . ? N3 C16 C15 105.66(12) . . ? N4 C17 N5 123.11(12) . . ? N4 C17 C18 129.14(12) . . ? N5 C17 C18 105.86(12) . . ? C19 C18 C23 120.80(13) . . ? C19 C18 C17 131.26(13) . . ? C23 C18 C17 107.27(12) . . ? C20 C19 C18 117.97(14) . . ? C20 C19 H19A 121.0 . . ? C18 C19 H19A 121.0 . . ? C19 C20 C21 121.36(13) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 121.35(14) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C21 C22 C23 118.16(14) . . ? C21 C22 H22A 120.9 . . ? C23 C22 H22A 120.9 . . ? C22 C23 C18 120.35(12) . . ? C22 C23 C24 132.00(13) . . ? C18 C23 C24 106.92(12) . . ? N6 C24 N5 122.36(12) . . ? N6 C24 C23 129.30(12) . . ? N5 C24 C23 106.15(11) . . ? O1 C25 C30 122.07(13) . . ? O1 C25 C26 118.40(12) . . ? C30 C25 C26 119.49(13) . . ? O2 C26 C25 121.87(13) . . ? O2 C26 C27 118.23(13) . . ? C25 C26 C27 119.90(13) . . ? C28 C27 C26 120.09(15) . . ? C28 C27 H27A 120.0 . . ? C26 C27 H27A 120.0 . . ? C27 C28 C29 120.21(14) . . ? C27 C28 H28A 119.9 . . ? C29 C28 H28A 119.9 . . ? C28 C29 C30 119.82(14) . . ? C28 C29 H29A 120.1 . . ? C30 C29 H29A 120.1 . . ? C29 C30 C25 120.42(14) . . ? C29 C30 H30A 119.8 . . ? C25 C30 H30A 119.8 . . ? O1 B1 N3 116.07(12) . . ? O1 B1 N1 112.00(11) . . ? N3 B1 N1 103.91(11) . . ? O1 B1 N5 115.75(12) . . ? N3 B1 N5 103.35(11) . . ? N1 B1 N5 104.37(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1O N6 0.93(2) 2.06(2) 2.8863(16) 148.1(19) 7_566 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.233 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 949043'