# Electronic Supplementary Material (ESI) for Chemical Communications # 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_th2 _database_code_depnum_ccdc_archive 'CCDC 894158' #TrackingRef 'web_deposit_cif_file_0_guyclarkson_1343554653.th2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 B N O2' _chemical_formula_sum 'C18 H20 B N O2' _chemical_formula_weight 293.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' B B 0.0090 0.0039 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8044(3) _cell_length_b 12.8701(4) _cell_length_c 13.0240(3) _cell_angle_alpha 109.741(3) _cell_angle_beta 91.202(2) _cell_angle_gamma 106.800(3) _cell_volume 1617.65(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12834 _cell_measurement_theta_min 3.63 _cell_measurement_theta_max 70.66 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.607 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'ABSPACK(CrysAlis, Oxford Diffraction)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cobra. The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of 52 sets of exposures with different \f angles for the crystal; each 5 s at low angles and 20s at high angles covered 1.0\% in \w. The crystal-to-detector distance was 5.5 cm. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 10.2833 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 21989 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 67.99 _reflns_number_total 5791 _reflns_number_gt 5041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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^)+(0.0601P)^2^+0.2350P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5791 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 B101 B 0.90669(13) 0.02716(11) 0.29726(11) 0.0299(3) Uani 1 1 d . . . C102 C 1.05656(12) 0.10247(10) 0.33059(10) 0.0314(3) Uani 1 1 d . . . C103 C 1.15661(12) 0.11978(11) 0.26651(11) 0.0372(3) Uani 1 1 d . . . H103 H 1.1388 0.0854 0.1886 0.045 Uiso 1 1 calc R . . C104 C 1.28226(13) 0.18734(12) 0.31668(14) 0.0455(3) Uani 1 1 d . . . H104 H 1.3502 0.2002 0.2729 0.055 Uiso 1 1 calc R . . C105 C 1.30920(13) 0.23614(12) 0.43021(14) 0.0496(4) Uani 1 1 d . . . H105 H 1.3960 0.2808 0.4637 0.059 Uiso 1 1 calc R . . C106 C 1.21143(14) 0.22076(12) 0.49569(12) 0.0441(3) Uani 1 1 d . . . H106 H 1.2301 0.2545 0.5736 0.053 Uiso 1 1 calc R . . C107 C 1.08527(12) 0.15485(10) 0.44478(10) 0.0342(3) Uani 1 1 d . . . C108 C 0.96531(13) 0.13168(12) 0.50120(10) 0.0369(3) Uani 1 1 d . . . H10A H 0.9611 0.0698 0.5313 0.044 Uiso 1 1 calc R . . H10B H 0.9648 0.2030 0.5619 0.044 Uiso 1 1 calc R . . N109 N 0.85411(9) 0.09372(8) 0.41279(8) 0.0302(2) Uani 1 1 d . . . C110 C 0.80657(11) 0.19292(10) 0.40884(10) 0.0315(3) Uani 1 1 d . . . H11A H 0.8112 0.2039 0.3372 0.038 Uiso 1 1 calc R . . H11B H 0.8491 0.2674 0.4702 0.038 Uiso 1 1 calc R . . C111 C 0.66751(12) 0.12909(11) 0.42469(10) 0.0346(3) Uani 1 1 d . . . C112 C 0.72133(12) 0.03367(11) 0.43548(12) 0.0382(3) Uani 1 1 d . . . H11C H 0.7215 0.0294 0.5100 0.046 Uiso 1 1 calc R . . H11D H 0.6782 -0.0440 0.3788 0.046 Uiso 1 1 calc R . . C113 C 0.62082(13) 0.19421(12) 0.52888(11) 0.0417(3) Uani 1 1 d . . . H11E H 0.6871 0.2178 0.5920 0.063 Uiso 1 1 calc R . . H11F H 0.5392 0.1435 0.5399 0.063 Uiso 1 1 calc R . . H11G H 0.6061 0.2634 0.5221 0.063 Uiso 1 1 calc R . . C114 C 0.56808(13) 0.09042(14) 0.32432(12) 0.0490(4) Uani 1 1 d . . . H11H H 0.5551 0.1589 0.3143 0.074 Uiso 1 1 calc R . . H11I H 0.4851 0.0410 0.3348 0.074 Uiso 1 1 calc R . . H11J H 0.5998 0.0464 0.2590 0.074 Uiso 1 1 calc R . . O115 O 0.83250(8) 0.02749(7) 0.20192(7) 0.0328(2) Uani 1 1 d . . . C116 C 0.76273(11) -0.08583(11) 0.14262(10) 0.0330(3) Uani 1 1 d . . . C117 C 0.67849(13) -0.12775(13) 0.04692(11) 0.0423(3) Uani 1 1 d . . . H117 H 0.6601 -0.0771 0.0144 0.051 Uiso 1 1 calc R . . C118 C 0.62089(14) -0.24853(14) -0.00054(12) 0.0509(4) Uani 1 1 d . . . H118 H 0.5618 -0.2808 -0.0666 0.061 Uiso 1 1 calc R . . C119 C 0.64860(14) -0.32136(13) 0.04712(12) 0.0502(4) Uani 1 1 d . . . H119 H 0.6084 -0.4030 0.0129 0.060 Uiso 1 1 calc R . . C120 C 0.73459(13) -0.27805(11) 0.14468(12) 0.0419(3) Uani 1 1 d . . . H120 H 0.7537 -0.3285 0.1772 0.050 Uiso 1 1 calc R . . C121 C 0.79025(11) -0.15908(11) 0.19147(10) 0.0333(3) Uani 1 1 d . . . O122 O 0.87758(8) -0.09661(7) 0.28441(7) 0.0336(2) Uani 1 1 d . . . B201 B 0.99965(14) 0.54633(12) 0.24118(11) 0.0324(3) Uani 1 1 d . . . C202 C 1.11631(12) 0.64223(10) 0.21957(9) 0.0327(3) Uani 1 1 d . . . C203 C 1.12999(13) 0.75591(11) 0.22689(10) 0.0351(3) Uani 1 1 d . . . H203 H 1.0593 0.7861 0.2433 0.042 Uiso 1 1 calc R . . C204 C 1.24739(14) 0.82485(12) 0.21013(11) 0.0414(3) Uani 1 1 d . . . H204 H 1.2572 0.9028 0.2170 0.050 Uiso 1 1 calc R . . C205 C 1.35039(14) 0.78081(13) 0.18345(12) 0.0467(3) Uani 1 1 d . . . H205 H 1.4298 0.8285 0.1716 0.056 Uiso 1 1 calc R . . C206 C 1.33788(14) 0.66769(13) 0.17408(11) 0.0443(3) Uani 1 1 d . . . H206 H 1.4077 0.6368 0.1550 0.053 Uiso 1 1 calc R . . C207 C 1.22156(13) 0.60050(11) 0.19300(10) 0.0371(3) Uani 1 1 d . . . C208 C 1.19244(13) 0.47842(12) 0.19238(11) 0.0407(3) Uani 1 1 d . . . H20A H 1.2291 0.4314 0.1314 0.049 Uiso 1 1 calc R . . H20B H 1.2295 0.4791 0.2628 0.049 Uiso 1 1 calc R . . N209 N 1.04781(10) 0.43106(9) 0.17681(8) 0.0344(2) Uani 1 1 d . . . C210 C 0.98501(14) 0.36480(11) 0.05746(10) 0.0388(3) Uani 1 1 d . . . H21A H 1.0491 0.3572 0.0044 0.047 Uiso 1 1 calc R . . H21B H 0.9194 0.3956 0.0347 0.047 Uiso 1 1 calc R . . C211 C 0.92423(13) 0.25262(11) 0.08281(10) 0.0368(3) Uani 1 1 d . . . C212 C 0.99429(14) 0.32121(11) 0.20177(10) 0.0382(3) Uani 1 1 d . . . H21C H 0.9337 0.3280 0.2578 0.046 Uiso 1 1 calc R . . H21D H 1.0629 0.2916 0.2212 0.046 Uiso 1 1 calc R . . C213 C 0.77707(14) 0.21457(13) 0.07712(12) 0.0455(3) Uani 1 1 d . . . H21E H 0.7489 0.2824 0.1137 0.068 Uiso 1 1 calc R . . H21F H 0.7495 0.1583 0.1140 0.068 Uiso 1 1 calc R . . H21G H 0.7376 0.1784 -0.0001 0.068 Uiso 1 1 calc R . . C214 C 0.97347(15) 0.15272(12) 0.01878(11) 0.0439(3) Uani 1 1 d . . . H21H H 0.9399 0.1250 -0.0594 0.066 Uiso 1 1 calc R . . H21I H 0.9432 0.0891 0.0466 0.066 Uiso 1 1 calc R . . H21J H 1.0690 0.1799 0.0279 0.066 Uiso 1 1 calc R . . O215 O 0.86581(8) 0.52660(7) 0.19768(7) 0.0365(2) Uani 1 1 d . . . C216 C 0.79017(13) 0.50581(10) 0.27595(11) 0.0374(3) Uani 1 1 d . . . C217 C 0.65642(14) 0.47447(12) 0.26919(14) 0.0494(4) Uani 1 1 d . . . H217 H 0.6039 0.4648 0.2051 0.059 Uiso 1 1 calc R . . C218 C 0.60109(16) 0.45743(13) 0.36070(17) 0.0590(5) Uani 1 1 d . . . H218 H 0.5090 0.4358 0.3589 0.071 Uiso 1 1 calc R . . C219 C 0.67766(17) 0.47145(13) 0.45352(15) 0.0574(5) Uani 1 1 d . . . H219 H 0.6372 0.4590 0.5143 0.069 Uiso 1 1 calc R . . C220 C 0.81351(16) 0.50354(12) 0.46014(12) 0.0461(3) Uani 1 1 d . . . H220 H 0.8663 0.5128 0.5239 0.055 Uiso 1 1 calc R . . C221 C 0.86740(13) 0.52111(10) 0.37008(11) 0.0359(3) Uani 1 1 d . . . O222 O 0.99654(8) 0.55431(7) 0.35734(7) 0.0343(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B101 0.0312(7) 0.0266(6) 0.0319(6) 0.0090(5) 0.0071(5) 0.0107(5) C102 0.0309(6) 0.0247(6) 0.0387(6) 0.0093(5) 0.0041(5) 0.0117(5) C103 0.0332(6) 0.0318(6) 0.0486(7) 0.0131(5) 0.0102(5) 0.0144(5) C104 0.0299(7) 0.0370(7) 0.0722(10) 0.0198(7) 0.0128(6) 0.0137(6) C105 0.0271(7) 0.0351(7) 0.0781(11) 0.0110(7) -0.0046(6) 0.0094(6) C106 0.0412(7) 0.0342(7) 0.0501(8) 0.0030(6) -0.0088(6) 0.0171(6) C107 0.0343(6) 0.0281(6) 0.0403(6) 0.0077(5) 0.0012(5) 0.0157(5) C108 0.0423(7) 0.0388(7) 0.0318(6) 0.0089(5) 0.0033(5) 0.0207(6) N109 0.0300(5) 0.0273(5) 0.0351(5) 0.0117(4) 0.0071(4) 0.0110(4) C110 0.0309(6) 0.0265(6) 0.0386(6) 0.0114(5) 0.0057(5) 0.0115(5) C111 0.0292(6) 0.0320(6) 0.0404(7) 0.0093(5) 0.0070(5) 0.0106(5) C112 0.0362(7) 0.0318(6) 0.0491(7) 0.0165(6) 0.0176(6) 0.0112(5) C113 0.0367(7) 0.0429(7) 0.0446(7) 0.0106(6) 0.0111(5) 0.0168(6) C114 0.0320(7) 0.0547(9) 0.0481(8) 0.0059(7) 0.0014(6) 0.0110(6) O115 0.0336(4) 0.0276(4) 0.0331(4) 0.0085(3) 0.0019(3) 0.0068(3) C116 0.0279(6) 0.0315(6) 0.0328(6) 0.0053(5) 0.0085(5) 0.0066(5) C117 0.0365(7) 0.0464(8) 0.0353(7) 0.0062(6) 0.0048(5) 0.0102(6) C118 0.0380(7) 0.0517(9) 0.0401(7) -0.0029(6) 0.0039(6) 0.0033(6) C119 0.0426(8) 0.0343(7) 0.0500(8) -0.0038(6) 0.0160(6) -0.0007(6) C120 0.0402(7) 0.0295(6) 0.0487(8) 0.0070(6) 0.0182(6) 0.0075(5) C121 0.0292(6) 0.0302(6) 0.0355(6) 0.0064(5) 0.0114(5) 0.0079(5) O122 0.0357(5) 0.0267(4) 0.0371(4) 0.0095(3) 0.0052(3) 0.0103(3) B201 0.0369(7) 0.0279(7) 0.0306(7) 0.0071(5) 0.0082(5) 0.0115(6) C202 0.0373(7) 0.0313(6) 0.0255(5) 0.0063(5) 0.0068(5) 0.0094(5) C203 0.0413(7) 0.0331(6) 0.0286(6) 0.0091(5) 0.0061(5) 0.0106(5) C204 0.0496(8) 0.0336(7) 0.0360(7) 0.0128(5) 0.0075(6) 0.0056(6) C205 0.0435(8) 0.0468(8) 0.0418(7) 0.0156(6) 0.0138(6) 0.0022(6) C206 0.0401(7) 0.0475(8) 0.0418(7) 0.0112(6) 0.0162(6) 0.0135(6) C207 0.0397(7) 0.0365(7) 0.0315(6) 0.0078(5) 0.0104(5) 0.0116(6) C208 0.0412(7) 0.0389(7) 0.0427(7) 0.0105(6) 0.0142(6) 0.0178(6) N209 0.0426(6) 0.0291(5) 0.0312(5) 0.0098(4) 0.0111(4) 0.0117(4) C210 0.0545(8) 0.0308(6) 0.0300(6) 0.0090(5) 0.0114(5) 0.0136(6) C211 0.0508(8) 0.0286(6) 0.0316(6) 0.0101(5) 0.0115(5) 0.0139(6) C212 0.0528(8) 0.0294(6) 0.0343(6) 0.0120(5) 0.0113(6) 0.0148(6) C213 0.0526(8) 0.0421(7) 0.0411(7) 0.0148(6) 0.0100(6) 0.0137(6) C214 0.0609(9) 0.0323(7) 0.0382(7) 0.0095(5) 0.0149(6) 0.0176(6) O215 0.0355(5) 0.0337(5) 0.0374(5) 0.0103(4) 0.0061(4) 0.0098(4) C216 0.0364(7) 0.0242(6) 0.0481(7) 0.0084(5) 0.0130(5) 0.0093(5) C217 0.0383(7) 0.0303(7) 0.0715(10) 0.0097(6) 0.0111(7) 0.0088(6) C218 0.0427(8) 0.0347(8) 0.0957(13) 0.0185(8) 0.0337(9) 0.0106(6) C219 0.0642(10) 0.0388(8) 0.0787(12) 0.0260(8) 0.0455(9) 0.0218(7) C220 0.0608(9) 0.0354(7) 0.0510(8) 0.0182(6) 0.0298(7) 0.0231(7) C221 0.0402(7) 0.0254(6) 0.0429(7) 0.0101(5) 0.0174(5) 0.0130(5) O222 0.0367(5) 0.0341(4) 0.0319(4) 0.0103(3) 0.0110(3) 0.0122(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 B101 O115 1.4657(16) . ? B101 O122 1.4807(15) . ? B101 C102 1.5902(18) . ? B101 N109 1.6635(16) . ? C102 C103 1.3925(18) . ? C102 C107 1.3946(17) . ? C103 C104 1.3865(19) . ? C103 H103 0.9500 . ? C104 C105 1.384(2) . ? C104 H104 0.9500 . ? C105 C106 1.383(2) . ? C105 H105 0.9500 . ? C106 C107 1.3896(18) . ? C106 H106 0.9500 . ? C107 C108 1.5077(18) . ? C108 N109 1.4935(16) . ? C108 H10A 0.9900 . ? C108 H10B 0.9900 . ? N109 C112 1.5080(15) . ? N109 C110 1.5228(15) . ? C110 C111 1.5457(16) . ? C110 H11A 0.9900 . ? C110 H11B 0.9900 . ? C111 C113 1.5175(17) . ? C111 C114 1.5176(18) . ? C111 C112 1.5467(18) . ? C112 H11C 0.9900 . ? C112 H11D 0.9900 . ? C113 H11E 0.9800 . ? C113 H11F 0.9800 . ? C113 H11G 0.9800 . ? C114 H11H 0.9800 . ? C114 H11I 0.9800 . ? C114 H11J 0.9800 . ? O115 C116 1.3678(14) . ? C116 C117 1.3738(18) . ? C116 C121 1.3933(19) . ? C117 C118 1.400(2) . ? C117 H117 0.9500 . ? C118 C119 1.379(2) . ? C118 H118 0.9500 . ? C119 C120 1.400(2) . ? C119 H119 0.9500 . ? C120 C121 1.3782(18) . ? C120 H120 0.9500 . ? C121 O122 1.3631(15) . ? B201 O215 1.4604(17) . ? B201 O222 1.4831(16) . ? B201 C202 1.5942(18) . ? B201 N209 1.6730(17) . ? C202 C207 1.3947(18) . ? C202 C203 1.3971(18) . ? C203 C204 1.3913(19) . ? C203 H203 0.9500 . ? C204 C205 1.389(2) . ? C204 H204 0.9500 . ? C205 C206 1.385(2) . ? C205 H205 0.9500 . ? C206 C207 1.3845(19) . ? C206 H206 0.9500 . ? C207 C208 1.5076(19) . ? C208 N209 1.4857(17) . ? C208 H20A 0.9900 . ? C208 H20B 0.9900 . ? N209 C212 1.5114(16) . ? N209 C210 1.5263(16) . ? C210 C211 1.5517(17) . ? C210 H21A 0.9900 . ? C210 H21B 0.9900 . ? C211 C213 1.515(2) . ? C211 C214 1.5236(18) . ? C211 C212 1.5470(18) . ? C212 H21C 0.9900 . ? C212 H21D 0.9900 . ? C213 H21E 0.9800 . ? C213 H21F 0.9800 . ? C213 H21G 0.9800 . ? C214 H21H 0.9800 . ? C214 H21I 0.9800 . ? C214 H21J 0.9800 . ? O215 C216 1.3680(16) . ? C216 C217 1.3756(19) . ? C216 C221 1.392(2) . ? C217 C218 1.399(2) . ? C217 H217 0.9500 . ? C218 C219 1.379(3) . ? C218 H218 0.9500 . ? C219 C220 1.397(2) . ? C219 H219 0.9500 . ? C220 C221 1.3776(19) . ? C220 H220 0.9500 . ? C221 O222 1.3674(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O115 B101 O122 105.90(9) . . ? O115 B101 C102 119.70(10) . . ? O122 B101 C102 115.01(10) . . ? O115 B101 N109 110.21(9) . . ? O122 B101 N109 107.86(9) . . ? C102 B101 N109 97.43(9) . . ? C103 C102 C107 118.83(11) . . ? C103 C102 B101 131.11(11) . . ? C107 C102 B101 110.04(11) . . ? C104 C103 C102 119.87(13) . . ? C104 C103 H103 120.1 . . ? C102 C103 H103 120.1 . . ? C105 C104 C103 120.34(13) . . ? C105 C104 H104 119.8 . . ? C103 C104 H104 119.8 . . ? C106 C105 C104 120.90(13) . . ? C106 C105 H105 119.5 . . ? C104 C105 H105 119.5 . . ? C105 C106 C107 118.44(14) . . ? C105 C106 H106 120.8 . . ? C107 C106 H106 120.8 . . ? C106 C107 C102 121.59(13) . . ? C106 C107 C108 126.43(12) . . ? C102 C107 C108 111.98(11) . . ? N109 C108 C107 104.47(10) . . ? N109 C108 H10A 110.9 . . ? C107 C108 H10A 110.9 . . ? N109 C108 H10B 110.9 . . ? C107 C108 H10B 110.9 . . ? H10A C108 H10B 108.9 . . ? C108 N109 C112 116.67(10) . . ? C108 N109 C110 113.25(9) . . ? C112 N109 C110 89.74(8) . . ? C108 N109 B101 105.06(9) . . ? C112 N109 B101 118.12(9) . . ? C110 N109 B101 113.91(9) . . ? N109 C110 C111 91.02(9) . . ? N109 C110 H11A 113.5 . . ? C111 C110 H11A 113.5 . . ? N109 C110 H11B 113.5 . . ? C111 C110 H11B 113.5 . . ? H11A C110 H11B 110.8 . . ? C113 C111 C114 111.57(11) . . ? C113 C111 C110 114.07(10) . . ? C114 C111 C110 113.02(11) . . ? C113 C111 C112 113.71(11) . . ? C114 C111 C112 115.06(11) . . ? C110 C111 C112 87.49(9) . . ? N109 C112 C111 91.55(9) . . ? N109 C112 H11C 113.4 . . ? C111 C112 H11C 113.4 . . ? N109 C112 H11D 113.4 . . ? C111 C112 H11D 113.4 . . ? H11C C112 H11D 110.7 . . ? C111 C113 H11E 109.5 . . ? C111 C113 H11F 109.5 . . ? H11E C113 H11F 109.5 . . ? C111 C113 H11G 109.5 . . ? H11E C113 H11G 109.5 . . ? H11F C113 H11G 109.5 . . ? C111 C114 H11H 109.5 . . ? C111 C114 H11I 109.5 . . ? H11H C114 H11I 109.5 . . ? C111 C114 H11J 109.5 . . ? H11H C114 H11J 109.5 . . ? H11I C114 H11J 109.5 . . ? C116 O115 B101 106.72(9) . . ? O115 C116 C117 127.55(12) . . ? O115 C116 C121 110.32(11) . . ? C117 C116 C121 122.11(12) . . ? C116 C117 C118 117.04(14) . . ? C116 C117 H117 121.5 . . ? C118 C117 H117 121.5 . . ? C119 C118 C117 121.02(14) . . ? C119 C118 H118 119.5 . . ? C117 C118 H118 119.5 . . ? C118 C119 C120 121.66(13) . . ? C118 C119 H119 119.2 . . ? C120 C119 H119 119.2 . . ? C121 C120 C119 117.08(14) . . ? C121 C120 H120 121.5 . . ? C119 C120 H120 121.5 . . ? O122 C121 C120 128.13(13) . . ? O122 C121 C116 110.76(10) . . ? C120 C121 C116 121.09(12) . . ? C121 O122 B101 106.24(9) . . ? O215 B201 O222 106.06(10) . . ? O215 B201 C202 119.60(11) . . ? O222 B201 C202 115.77(10) . . ? O215 B201 N209 110.55(10) . . ? O222 B201 N209 106.34(10) . . ? C202 B201 N209 97.56(9) . . ? C207 C202 C203 118.23(12) . . ? C207 C202 B201 110.18(11) . . ? C203 C202 B201 131.55(11) . . ? C204 C203 C202 119.87(12) . . ? C204 C203 H203 120.1 . . ? C202 C203 H203 120.1 . . ? C205 C204 C203 120.61(13) . . ? C205 C204 H204 119.7 . . ? C203 C204 H204 119.7 . . ? C206 C205 C204 120.32(13) . . ? C206 C205 H205 119.8 . . ? C204 C205 H205 119.8 . . ? C207 C206 C205 118.64(13) . . ? C207 C206 H206 120.7 . . ? C205 C206 H206 120.7 . . ? C206 C207 C202 122.31(13) . . ? C206 C207 C208 126.19(12) . . ? C202 C207 C208 111.46(11) . . ? N209 C208 C207 104.88(10) . . ? N209 C208 H20A 110.8 . . ? C207 C208 H20A 110.8 . . ? N209 C208 H20B 110.8 . . ? C207 C208 H20B 110.8 . . ? H20A C208 H20B 108.8 . . ? C208 N209 C212 114.67(10) . . ? C208 N209 C210 115.00(10) . . ? C212 N209 C210 89.75(9) . . ? C208 N209 B201 104.36(9) . . ? C212 N209 B201 119.30(9) . . ? C210 N209 B201 113.97(10) . . ? N209 C210 C211 90.94(9) . . ? N209 C210 H21A 113.5 . . ? C211 C210 H21A 113.5 . . ? N209 C210 H21B 113.5 . . ? C211 C210 H21B 113.5 . . ? H21A C210 H21B 110.8 . . ? C213 C211 C214 112.08(11) . . ? C213 C211 C212 112.77(11) . . ? C214 C211 C212 114.07(11) . . ? C213 C211 C210 115.14(11) . . ? C214 C211 C210 113.20(11) . . ? C212 C211 C210 87.53(9) . . ? N209 C212 C211 91.69(9) . . ? N209 C212 H21C 113.3 . . ? C211 C212 H21C 113.3 . . ? N209 C212 H21D 113.3 . . ? C211 C212 H21D 113.3 . . ? H21C C212 H21D 110.7 . . ? C211 C213 H21E 109.5 . . ? C211 C213 H21F 109.5 . . ? H21E C213 H21F 109.5 . . ? C211 C213 H21G 109.5 . . ? H21E C213 H21G 109.5 . . ? H21F C213 H21G 109.5 . . ? C211 C214 H21H 109.5 . . ? C211 C214 H21I 109.5 . . ? H21H C214 H21I 109.5 . . ? C211 C214 H21J 109.5 . . ? H21H C214 H21J 109.5 . . ? H21I C214 H21J 109.5 . . ? C216 O215 B201 106.22(10) . . ? O215 C216 C217 127.77(14) . . ? O215 C216 C221 110.67(11) . . ? C217 C216 C221 121.56(13) . . ? C216 C217 C218 117.12(16) . . ? C216 C217 H217 121.4 . . ? C218 C217 H217 121.4 . . ? C219 C218 C217 121.27(14) . . ? C219 C218 H218 119.4 . . ? C217 C218 H218 119.4 . . ? C218 C219 C220 121.43(14) . . ? C218 C219 H219 119.3 . . ? C220 C219 H219 119.3 . . ? C221 C220 C219 116.99(16) . . ? C221 C220 H220 121.5 . . ? C219 C220 H220 121.5 . . ? O222 C221 C220 127.97(13) . . ? O222 C221 C216 110.41(11) . . ? C220 C221 C216 121.62(13) . . ? C221 O222 B201 105.68(10) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.237 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.035