Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Katherine Franz' 'Louise K. Charkoudian' 'Ashley M. Kwon' 'David M. Pham' 'Abbey D. Vangeloff' _publ_contact_author_name 'Katherine Franz' _publ_contact_author_address ; Department of Chemistry Duke University PO Box 90346 Durham NC 27708 0346 UNITED STATES OF AMERICA ; _publ_contact_author_email KATHERINE.FRANZ@DUKE.EDU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Modifications of boronic ester pro-chelators triggered by hydrogen peroxide tune reactivity to inhibit metal-promoted oxidative stress ; data_dp234 _database_code_depnum_ccdc_archive 'CCDC 643169' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Fe(SBH(OMe)3)2]NO3 - pentanes' _chemical_melting_point ? _chemical_formula_moiety 'C34 H34 Fe N4 O10, C5, N O3' _chemical_formula_sum 'C39 H34 Fe N5 O13' _chemical_formula_weight 836.56 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' Fe Fe 0.3463 0.8444 '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 11.7263(11) _cell_length_b 28.622(3) _cell_length_c 12.2079(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.464(5) _cell_angle_gamma 90.00 _cell_volume 4071.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5262 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 21.15 _exptl_crystal_description Needles _exptl_crystal_colour 'Black ' _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1732 _exptl_absorpt_coefficient_mu 0.440 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37545 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0888 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.72 _reflns_number_total 9433 _reflns_number_gt 4403 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex II 2.0 Rev.2 (Bruker, 2005)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT 7.12A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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. The refinement of the structure contain several different groups that must be fixed to rigid groups in order for convergence of the refinement. There are two orientations for one terminal methyl of the methoxy group on one of the two ligands, C16A and C16B. The occupancies at the two sites were which were refined to be [50:50]. They were refined isotropically. There are two orientations of one of the two 3,4,5-trimethoxyphenyl groups, and their occupancies were refined to be 87.5% [O7, O8, O9, C29 to C37] and 12.5% [O7a, O8a, O9a, C29a to C37a]. The minor orientation was first determined by finding the atomic sites on the difference map and then fixed to a rigid group with the AFIX 66 command. The methoxy groups were then determined from the difference map and once the good geometry was determined by several refinement cycles, the entire trimethoxyphenyl group was fixed as a rigid group with AFIX 3. Due to the freedom of movement of the methoxy groups, the thermal parameters of the terminal carbons are much larger than other carbons in the structure. The minor orientation was refined isotropically. There is a solvent site in the crystal latice that is occupied by two isomers of pentanes, n-pentane [C71 to C75] and cyclopentane [C81 to C85]. The occupancy of the two isomers were refined, but due to many other orientations, the refinement was not stable. The two representative orientations were determined and given 50% occupancy for each isomer. The bond lengths were fixed using DFIX in which the C-C distance was fixed at 1.540 angstroms. The thermal parameter of all the carbon sites of the solvent molecules were fixed at 0.180, which was the average value of the refined thermal parameters. All sites were refined isotropically. ; _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^)+(0.1605P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9433 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1673 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2733 _refine_ls_wR_factor_gt 0.2157 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 Fe1 Fe 0.32733(6) 0.38862(2) 0.75487(4) 0.0504(3) Uani 1 1 d . . . O1 O 0.1708(3) 0.36138(12) 0.7922(2) 0.0601(8) Uani 1 1 d . . . O2 O -0.2391(4) 0.30550(19) 0.8393(4) 0.1081(15) Uani 1 1 d . B . O3 O -0.2120(4) 0.26058(16) 1.0320(4) 0.1005(14) Uani 1 1 d . . . O4 O -0.0217(4) 0.26540(13) 1.1638(3) 0.0808(11) Uani 1 1 d . B . O5 O 0.4719(3) 0.41829(13) 0.7755(2) 0.0670(9) Uani 1 1 d . . . O6 O 0.2471(3) 0.45214(11) 0.7190(2) 0.0580(8) Uani 1 1 d . A . O7 O 0.0677(4) 0.61035(14) 0.7304(4) 0.0848(15) Uani 0.875(6) 1 d P A 1 O8 O -0.0203(4) 0.62826(16) 0.5258(4) 0.0852(15) Uani 0.875(6) 1 d P A 1 O9 O 0.0294(4) 0.57427(14) 0.3538(3) 0.0753(13) Uani 0.875(6) 1 d P A 1 O7A O 0.1268(4) 0.62846(14) 0.6822(3) 0.077(9) Uiso 0.125(6) 1 d PR A 2 O8A O 0.0258(4) 0.62951(14) 0.4632(3) 0.100 Uiso 0.125(6) 1 d PR A 2 O9A O 0.0875(4) 0.57251(14) 0.3132(3) 0.124(19) Uiso 0.125(6) 1 d PR A 2 O10 O 0.3818(3) 0.32769(11) 0.7342(2) 0.0668(10) Uani 1 1 d . . . N1 N 0.3331(3) 0.39382(12) 0.9283(3) 0.0495(9) Uani 1 1 d . . . N2 N 0.2375(3) 0.37527(13) 0.9678(3) 0.0552(10) Uani 1 1 d . . . H2A H 0.2299 0.3750 1.0371 0.066 Uiso 1 1 calc R . . N3 N 0.2835(3) 0.38851(12) 0.5840(3) 0.0457(8) Uani 1 1 d . . . N4 N 0.2375(3) 0.43061(13) 0.5432(3) 0.0520(9) Uani 1 1 d . A . H3A H 0.2219 0.4358 0.4737 0.062 Uiso 1 1 calc R . . C1 C 0.5390(4) 0.43637(17) 0.8580(4) 0.0589(12) Uani 1 1 d . . . C2 C 0.6365(5) 0.4606(2) 0.8374(5) 0.0724(15) Uani 1 1 d . . . H2B H 0.6536 0.4630 0.7651 0.087 Uiso 1 1 calc R . . C3 C 0.7079(5) 0.4808(2) 0.9187(5) 0.0841(17) Uani 1 1 d . . . H3B H 0.7732 0.4964 0.9020 0.101 Uiso 1 1 calc R . . C4 C 0.6832(5) 0.4780(2) 1.0269(5) 0.0815(17) Uani 1 1 d . . . H4A H 0.7319 0.4919 1.0830 0.098 Uiso 1 1 calc R . . C5 C 0.5872(5) 0.4547(2) 1.0513(4) 0.0728(15) Uani 1 1 d . . . H5A H 0.5712 0.4529 1.1240 0.087 Uiso 1 1 calc R . . C6 C 0.5127(4) 0.43365(17) 0.9678(4) 0.0576(12) Uani 1 1 d . . . C7 C 0.4111(4) 0.41185(17) 0.9974(3) 0.0576(12) Uani 1 1 d . . . H7A H 0.4008 0.4106 1.0718 0.069 Uiso 1 1 calc R . . C8 C 0.1577(4) 0.35787(15) 0.8934(3) 0.0505(11) Uani 1 1 d . . . C9 C 0.0584(4) 0.33413(15) 0.9315(3) 0.0504(11) Uani 1 1 d . . . C10 C -0.0432(5) 0.33246(18) 0.8634(4) 0.0640(13) Uani 1 1 d . B . H10A H -0.0494 0.3470 0.7948 0.077 Uiso 1 1 calc R . . C11 C -0.1351(5) 0.3092(2) 0.8970(5) 0.0743(15) Uani 1 1 d . . . C12 C -0.1245(5) 0.28655(19) 0.9994(5) 0.0716(15) Uani 1 1 d . B . C13 C -0.0218(5) 0.28820(17) 1.0670(4) 0.0633(13) Uani 1 1 d . . . C14 C 0.0702(4) 0.31190(16) 1.0331(4) 0.0553(12) Uani 1 1 d . B . H14A H 0.1397 0.3130 1.0780 0.066 Uiso 1 1 calc R . . C15 C -0.2622(7) 0.3300(3) 0.7424(7) 0.140(3) Uani 1 1 d . . . H15A H -0.3389 0.3232 0.7102 0.210 Uiso 1 1 calc R B . H15B H -0.2087 0.3211 0.6922 0.210 Uiso 1 1 calc R . . H15C H -0.2551 0.3629 0.7573 0.210 Uiso 1 1 calc R . . C16A C -0.2742(17) 0.2844(6) 1.1123(15) 0.132(6) Uiso 0.50 1 d P B 1 H16A H -0.3347 0.2646 1.1321 0.198 Uiso 0.50 1 calc PR B 1 H16B H -0.3063 0.3129 1.0810 0.198 Uiso 0.50 1 calc PR B 1 H16C H -0.2225 0.2914 1.1769 0.198 Uiso 0.50 1 calc PR B 1 C16B C -0.3111(19) 0.2801(8) 1.0336(18) 0.156(7) Uiso 0.50 1 d P B 2 H16D H -0.3545 0.2772 0.9624 0.235 Uiso 0.50 1 calc PR B 2 H16E H -0.3009 0.3126 1.0516 0.235 Uiso 0.50 1 calc PR B 2 H16F H -0.3517 0.2651 1.0879 0.235 Uiso 0.50 1 calc PR B 2 C17 C 0.0804(6) 0.2694(2) 1.2423(5) 0.103(2) Uani 1 1 d . . . H17A H 0.0703 0.2516 1.3071 0.154 Uiso 1 1 calc R B . H17B H 0.0929 0.3017 1.2621 0.154 Uiso 1 1 calc R . . H17C H 0.1455 0.2577 1.2097 0.154 Uiso 1 1 calc R . . C21 C 0.3753(4) 0.29751(15) 0.6518(3) 0.0498(11) Uani 1 1 d . . . C22 C 0.4135(5) 0.25245(19) 0.6707(4) 0.0702(15) Uani 1 1 d . . . H22A H 0.4424 0.2436 0.7417 0.084 Uiso 1 1 calc R . . C23 C 0.4098(5) 0.22000(18) 0.5865(4) 0.0720(15) Uani 1 1 d . . . H23A H 0.4345 0.1896 0.6016 0.086 Uiso 1 1 calc R . . C24 C 0.3706(5) 0.23241(19) 0.4829(5) 0.0708(15) Uani 1 1 d . . . H24A H 0.3707 0.2108 0.4261 0.085 Uiso 1 1 calc R . . C25 C 0.3309(5) 0.27644(18) 0.4606(4) 0.0635(13) Uani 1 1 d . . . H25A H 0.3032 0.2844 0.3886 0.076 Uiso 1 1 calc R . . C26 C 0.3309(4) 0.30990(16) 0.5440(3) 0.0490(11) Uani 1 1 d . . . C27 C 0.2880(4) 0.35512(16) 0.5140(3) 0.0520(11) Uani 1 1 d . . . H27A H 0.2619 0.3608 0.4404 0.062 Uiso 1 1 calc R . . C28 C 0.2195(4) 0.46235(15) 0.6193(3) 0.0493(11) Uani 1 1 d . . . C29 C 0.1671(5) 0.50728(18) 0.5885(8) 0.050(2) Uani 0.875(6) 1 d P A 1 C30 C 0.1480(7) 0.5381(2) 0.6731(7) 0.0601(15) Uani 0.875(6) 1 d P A 1 H30A H 0.1754 0.5306 0.7454 0.072 Uiso 0.875(6) 1 calc PR A 1 C31 C 0.0901(5) 0.5786(2) 0.6519(5) 0.0652(16) Uani 0.875(6) 1 d P A 1 C32 C 0.0501(5) 0.59003(19) 0.5463(5) 0.0603(15) Uani 0.875(6) 1 d P A 1 C33 C 0.0750(6) 0.5603(2) 0.4572(8) 0.0592(19) Uani 0.875(6) 1 d P A 1 C34 C 0.1319(5) 0.5188(2) 0.4806(9) 0.053(3) Uani 0.875(6) 1 d P A 1 H34A H 0.1465 0.4988 0.4240 0.063 Uiso 0.875(6) 1 calc PR A 1 C35 C 0.1077(8) 0.5993(3) 0.8392(6) 0.107(3) Uani 0.875(6) 1 d P A 1 H35A H 0.0869 0.6237 0.8871 0.161 Uiso 0.875(6) 1 calc PR A 1 H35B H 0.1897 0.5962 0.8464 0.161 Uiso 0.875(6) 1 calc PR A 1 H35C H 0.0740 0.5704 0.8592 0.161 Uiso 0.875(6) 1 calc PR A 1 C36 C 0.0248(9) 0.6674(3) 0.4823(7) 0.118(3) Uani 0.875(6) 1 d P A 1 H36A H -0.0326 0.6915 0.4735 0.177 Uiso 0.875(6) 1 calc PR A 1 H36B H 0.0491 0.6601 0.4118 0.177 Uiso 0.875(6) 1 calc PR A 1 H36C H 0.0893 0.6782 0.5311 0.177 Uiso 0.875(6) 1 calc PR A 1 C37 C 0.0557(6) 0.5478(3) 0.2624(5) 0.079(2) Uani 0.875(6) 1 d P A 1 H37A H 0.0194 0.5616 0.1958 0.119 Uiso 0.875(6) 1 calc PR A 1 H37B H 0.0281 0.5164 0.2688 0.119 Uiso 0.875(6) 1 calc PR A 1 H37C H 0.1373 0.5473 0.2606 0.119 Uiso 0.875(6) 1 calc PR A 1 C29A C 0.1792(6) 0.5086(3) 0.5678(5) 0.039(19) Uiso 0.125(6) 1 d PR A 2 C30A C 0.1755(6) 0.5439(3) 0.6454(5) 0.09(3) Uiso 0.125(6) 1 d PR A 2 H30B H 0.2046 0.5387 0.7185 0.106 Uiso 0.125(6) 1 calc PR A 2 C31A C 0.1285(6) 0.5871(3) 0.6139(5) 0.061(13) Uiso 0.125(6) 1 d PR A 2 C32A C 0.0851(6) 0.5949(3) 0.5047(5) 0.070 Uiso 0.125(6) 1 d PR A 2 C33A C 0.0888(6) 0.5596(3) 0.4271(5) 0.14(6) Uiso 0.125(6) 1 d PR A 2 C34A C 0.1359(6) 0.5164(3) 0.4587(5) 0.07(3) Uiso 0.125(6) 1 d PR A 2 H34B H 0.1383 0.4927 0.4068 0.078 Uiso 0.125(6) 1 calc PR A 2 C35A C 0.1851(6) 0.6215(3) 0.7905(5) 0.16(3) Uiso 0.125(6) 1 d PR A 2 H35D H 0.1818 0.6496 0.8326 0.243 Uiso 0.125(6) 1 calc PR A 2 H35E H 0.2638 0.6135 0.7851 0.243 Uiso 0.125(6) 1 calc PR A 2 H35F H 0.1488 0.5966 0.8262 0.243 Uiso 0.125(6) 1 calc PR A 2 C36A C 0.0242(6) 0.6750(3) 0.5371(5) 0.048(10) Uiso 0.125(6) 1 d PR A 2 H36D H -0.0226 0.6985 0.4980 0.071 Uiso 0.125(6) 1 calc PR A 2 H36E H 0.1010 0.6866 0.5537 0.071 Uiso 0.125(6) 1 calc PR A 2 H36F H -0.0067 0.6675 0.6045 0.071 Uiso 0.125(6) 1 calc PR A 2 C37A C 0.0702(6) 0.5297(3) 0.2514(5) 0.13(4) Uiso 0.125(6) 1 d PR A 2 H37D H 0.0685 0.5363 0.1741 0.201 Uiso 0.125(6) 1 calc PR A 2 H37E H -0.0014 0.5159 0.2653 0.201 Uiso 0.125(6) 1 calc PR A 2 H37F H 0.1318 0.5085 0.2736 0.201 Uiso 0.125(6) 1 calc PR A 2 N5 N 0.2021(5) 0.41190(18) 0.2315(3) 0.0767(13) Uani 1 1 d . . . O11 O 0.1587(5) 0.42529(16) 0.1419(3) 0.1060(15) Uani 1 1 d . . . O12 O 0.1929(5) 0.43621(17) 0.3133(3) 0.1183(18) Uani 1 1 d . . . O13 O 0.2542(4) 0.37548(17) 0.2356(4) 0.1230(18) Uani 1 1 d . . . C71 C 0.3703(4) 0.67652(17) 0.6350(4) 0.180 Uiso 0.50 1 d PR C 1 C72 C 0.4379(4) 0.63296(17) 0.6793(4) 0.180 Uiso 0.50 1 d PR C 1 C73 C 0.4456(4) 0.59854(17) 0.5829(4) 0.180 Uiso 0.50 1 d PR C 1 C74 C 0.4887(4) 0.55080(17) 0.6294(4) 0.180 Uiso 0.50 1 d PR C 1 C75 C 0.4950(4) 0.51626(17) 0.5336(4) 0.180 Uiso 0.50 1 d PR . 1 C81 C 0.4601(4) 0.58863(17) 0.6842(4) 0.180 Uiso 0.50 1 d PR C 2 C82 C 0.4104(4) 0.63838(17) 0.6700(4) 0.180 Uiso 0.50 1 d PR C 2 C83 C 0.3857(4) 0.63960(17) 0.5432(4) 0.180 Uiso 0.50 1 d PR C 2 C84 C 0.4118(4) 0.59556(17) 0.4787(4) 0.180 Uiso 0.50 1 d PR C 2 C85 C 0.4652(4) 0.56370(17) 0.5721(4) 0.180 Uiso 0.50 1 d PR C 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 Fe1 0.0637(5) 0.0520(4) 0.0354(3) -0.0046(3) 0.0055(3) 0.0045(3) O1 0.067(2) 0.069(2) 0.0428(16) 0.0008(15) 0.0040(14) -0.0050(17) O2 0.064(3) 0.134(4) 0.120(4) 0.011(3) -0.014(3) -0.013(3) O3 0.068(3) 0.103(3) 0.133(4) 0.007(3) 0.022(2) -0.012(2) O4 0.094(3) 0.068(3) 0.084(3) 0.008(2) 0.024(2) -0.014(2) O5 0.066(2) 0.084(3) 0.0525(18) -0.0060(17) 0.0125(16) -0.0035(19) O6 0.076(2) 0.051(2) 0.0465(16) -0.0081(13) 0.0069(15) 0.0074(16) O7 0.102(4) 0.058(3) 0.093(3) -0.023(2) 0.005(3) 0.025(2) O8 0.083(3) 0.056(3) 0.118(4) 0.012(3) 0.023(3) 0.018(2) O9 0.093(3) 0.058(3) 0.073(3) 0.012(2) 0.001(3) 0.020(2) O10 0.097(3) 0.060(2) 0.0418(15) -0.0002(14) 0.0015(16) 0.0199(19) N1 0.065(2) 0.048(2) 0.0369(17) -0.0040(15) 0.0073(17) -0.0038(19) N2 0.067(3) 0.064(3) 0.0363(17) -0.0063(17) 0.0112(18) -0.006(2) N3 0.056(2) 0.042(2) 0.0391(17) -0.0030(15) 0.0058(15) -0.0004(18) N4 0.072(3) 0.044(2) 0.0397(17) 0.0027(15) 0.0055(17) 0.0140(19) C1 0.060(3) 0.060(3) 0.055(3) -0.005(2) -0.002(2) 0.004(3) C2 0.063(4) 0.084(4) 0.071(3) -0.003(3) 0.012(3) -0.010(3) C3 0.068(4) 0.079(4) 0.105(5) -0.003(4) 0.007(3) -0.014(3) C4 0.072(4) 0.073(4) 0.093(4) -0.012(3) -0.020(3) -0.012(3) C5 0.084(4) 0.069(4) 0.064(3) -0.004(3) -0.001(3) -0.004(3) C6 0.060(3) 0.057(3) 0.054(3) -0.005(2) -0.002(2) -0.004(2) C7 0.073(3) 0.062(3) 0.036(2) -0.007(2) 0.001(2) -0.002(3) C8 0.062(3) 0.046(3) 0.044(2) -0.0075(19) 0.008(2) 0.004(2) C9 0.056(3) 0.044(3) 0.051(2) -0.0117(19) 0.009(2) 0.002(2) C10 0.064(3) 0.062(3) 0.067(3) -0.007(2) 0.009(3) 0.002(3) C11 0.056(4) 0.075(4) 0.092(4) -0.012(3) 0.009(3) 0.000(3) C12 0.059(4) 0.064(4) 0.095(4) -0.006(3) 0.023(3) -0.005(3) C13 0.070(4) 0.047(3) 0.075(3) -0.007(2) 0.021(3) 0.001(3) C14 0.057(3) 0.051(3) 0.059(3) -0.009(2) 0.010(2) -0.003(2) C15 0.094(6) 0.168(9) 0.148(8) 0.011(7) -0.030(5) -0.008(6) C17 0.124(6) 0.098(5) 0.082(4) 0.035(4) -0.002(4) -0.023(4) C21 0.056(3) 0.042(3) 0.053(2) -0.004(2) 0.011(2) 0.006(2) C22 0.088(4) 0.060(4) 0.064(3) 0.009(2) 0.014(3) 0.015(3) C23 0.094(4) 0.045(3) 0.078(3) -0.002(3) 0.016(3) 0.011(3) C24 0.083(4) 0.050(3) 0.080(4) -0.017(3) 0.012(3) 0.002(3) C25 0.078(4) 0.051(3) 0.060(3) -0.012(2) 0.005(2) 0.005(3) C26 0.056(3) 0.045(3) 0.047(2) -0.0037(19) 0.007(2) 0.000(2) C27 0.063(3) 0.054(3) 0.038(2) -0.0087(19) 0.002(2) 0.005(2) C28 0.055(3) 0.046(3) 0.048(2) -0.0085(19) 0.010(2) 0.001(2) C29 0.052(4) 0.041(4) 0.056(3) -0.004(2) 0.008(3) -0.001(2) C30 0.065(4) 0.050(4) 0.062(3) -0.013(3) -0.005(4) 0.010(3) C31 0.065(4) 0.054(4) 0.077(4) -0.010(3) 0.009(3) 0.008(3) C32 0.065(4) 0.036(3) 0.080(4) 0.005(3) 0.011(3) 0.008(3) C33 0.057(4) 0.046(4) 0.073(4) 0.006(3) -0.001(3) -0.003(3) C34 0.056(5) 0.043(4) 0.060(3) -0.002(3) 0.009(3) 0.006(3) C35 0.128(7) 0.092(6) 0.098(6) -0.053(5) -0.006(5) 0.038(5) C36 0.192(10) 0.054(5) 0.109(7) 0.024(4) 0.030(6) 0.009(5) C37 0.096(6) 0.070(5) 0.072(4) 0.030(4) 0.009(4) 0.016(4) N5 0.107(4) 0.076(3) 0.051(3) -0.009(2) 0.023(2) -0.008(3) O11 0.165(5) 0.103(3) 0.051(2) 0.003(2) 0.016(2) -0.016(3) O12 0.202(5) 0.108(4) 0.0445(19) -0.013(2) 0.012(3) 0.035(3) O13 0.146(5) 0.090(4) 0.135(4) -0.023(3) 0.024(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O10 1.884(3) . ? Fe1 O5 1.887(4) . ? Fe1 O6 2.071(3) . ? Fe1 O1 2.091(3) . ? Fe1 N3 2.091(3) . ? Fe1 N1 2.116(3) . ? O1 C8 1.266(5) . ? O2 C11 1.343(7) . ? O2 C15 1.376(9) . ? O3 C16B 1.29(2) . ? O3 C12 1.362(6) . ? O3 C16A 1.455(18) . ? O4 C13 1.349(6) . ? O4 C17 1.451(7) . ? O5 C1 1.312(5) . ? O6 C28 1.257(5) . ? O7 C31 1.367(7) . ? O7 C35 1.395(9) . ? O8 C36 1.372(8) . ? O8 C32 1.376(7) . ? O9 C33 1.373(8) . ? O9 C37 1.411(9) . ? O7A C35A 1.433(7) . ? O7A C31A 1.449(10) . ? O8A C32A 1.281(9) . ? O8A C36A 1.586(10) . ? O9A C33A 1.438(7) . ? O9A C37A 1.441(10) . ? O10 C21 1.322(5) . ? N1 C7 1.281(6) . ? N1 N2 1.376(5) . ? N2 C8 1.325(5) . ? N2 H2A 0.8600 . ? N3 C27 1.287(5) . ? N3 N4 1.390(5) . ? N4 C28 1.333(5) . ? N4 H3A 0.8600 . ? C1 C2 1.384(7) . ? C1 C6 1.411(6) . ? C2 C3 1.354(8) . ? C2 H2B 0.9300 . ? C3 C4 1.386(8) . ? C3 H3B 0.9300 . ? C4 C5 1.369(8) . ? C4 H4A 0.9300 . ? C5 C6 1.402(7) . ? C5 H5A 0.9300 . ? C6 C7 1.427(7) . ? C7 H7A 0.9300 . ? C8 C9 1.468(6) . ? C9 C10 1.375(7) . ? C9 C14 1.387(6) . ? C10 C11 1.368(8) . ? C10 H10A 0.9300 . ? C11 C12 1.401(8) . ? C12 C13 1.383(8) . ? C13 C14 1.377(7) . ? C14 H14A 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16A H16A 0.9600 . ? C16A H16B 0.9600 . ? C16A H16C 0.9600 . ? C16B H16D 0.9600 . ? C16B H16E 0.9600 . ? C16B H16F 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C21 C22 1.376(7) . ? C21 C26 1.404(6) . ? C22 C23 1.382(7) . ? C22 H22A 0.9300 . ? C23 C24 1.344(7) . ? C23 H23A 0.9300 . ? C24 C25 1.361(7) . ? C24 H24A 0.9300 . ? C25 C26 1.398(6) . ? C25 H25A 0.9300 . ? C26 C27 1.422(6) . ? C27 H27A 0.9300 . ? C28 C29 1.456(7) . ? C28 C29A 1.517(9) . ? C29 C34 1.376(10) . ? C29 C30 1.394(10) . ? C30 C31 1.354(8) . ? C30 H30A 0.9300 . ? C31 C32 1.362(8) . ? C32 C33 1.437(11) . ? C33 C34 1.376(8) . ? C34 H34A 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C29A C34A 1.3899 . ? C29A C30A 1.3899 . ? C30A C31A 1.3901 . ? C30A H30B 0.9300 . ? C31A C32A 1.3903 . ? C32A C33A 1.3900 . ? C33A C34A 1.3902 . ? C34A H34B 0.9300 . ? C35A H35D 0.9600 . ? C35A H35E 0.9600 . ? C35A H35F 0.9600 . ? C36A H36D 0.9600 . ? C36A H36E 0.9600 . ? C36A H36F 0.9600 . ? C37A H37D 0.9600 . ? C37A H37E 0.9600 . ? C37A H37F 0.9600 . ? N5 O13 1.207(6) . ? N5 O11 1.215(6) . ? N5 O12 1.232(5) . ? C71 C72 1.5419 . ? C72 C73 1.5453 . ? C73 C74 1.5430 . ? C74 C75 1.5397 . ? C75 C75 1.255(9) 3_666 ? C81 C82 1.5413 . ? C81 C85 1.5504 . ? C82 C83 1.5424 . ? C83 C84 1.5349 . ? C84 C85 1.5369 . ? 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 O10 Fe1 O5 96.98(16) . . ? O10 Fe1 O6 159.56(12) . . ? O5 Fe1 O6 90.75(14) . . ? O10 Fe1 O1 90.19(15) . . ? O5 Fe1 O1 159.35(12) . . ? O6 Fe1 O1 89.11(13) . . ? O10 Fe1 N3 85.07(13) . . ? O5 Fe1 N3 104.49(13) . . ? O6 Fe1 N3 74.66(12) . . ? O1 Fe1 N3 95.38(13) . . ? O10 Fe1 N1 103.07(13) . . ? O5 Fe1 N1 84.69(14) . . ? O6 Fe1 N1 96.46(13) . . ? O1 Fe1 N1 74.81(13) . . ? N3 Fe1 N1 167.08(14) . . ? C8 O1 Fe1 116.6(3) . . ? C11 O2 C15 119.3(6) . . ? C16B O3 C12 118.4(11) . . ? C12 O3 C16A 113.1(9) . . ? C13 O4 C17 117.3(4) . . ? C1 O5 Fe1 137.1(3) . . ? C28 O6 Fe1 118.0(3) . . ? C31 O7 C35 116.5(5) . . ? C36 O8 C32 118.1(6) . . ? C33 O9 C37 118.2(5) . . ? C35A O7A C31A 112.4(6) . . ? C32A O8A C36A 116.8(5) . . ? C33A O9A C37A 105.8(5) . . ? C21 O10 Fe1 135.7(3) . . ? C7 N1 N2 118.3(3) . . ? C7 N1 Fe1 128.9(3) . . ? N2 N1 Fe1 112.8(3) . . ? C8 N2 N1 116.4(3) . . ? C8 N2 H2A 121.8 . . ? N1 N2 H2A 121.8 . . ? C27 N3 N4 116.7(3) . . ? C27 N3 Fe1 129.8(3) . . ? N4 N3 Fe1 113.5(2) . . ? C28 N4 N3 115.2(3) . . ? C28 N4 H3A 122.4 . . ? N3 N4 H3A 122.4 . . ? O5 C1 C2 119.6(4) . . ? O5 C1 C6 122.1(5) . . ? C2 C1 C6 118.3(5) . . ? C3 C2 C1 122.4(5) . . ? C3 C2 H2B 118.8 . . ? C1 C2 H2B 118.8 . . ? C2 C3 C4 119.8(6) . . ? C2 C3 H3B 120.1 . . ? C4 C3 H3B 120.1 . . ? C5 C4 C3 120.0(5) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C5 C6 120.8(5) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C5 C6 C1 118.8(5) . . ? C5 C6 C7 118.3(4) . . ? C1 C6 C7 122.9(4) . . ? N1 C7 C6 124.3(4) . . ? N1 C7 H7A 117.9 . . ? C6 C7 H7A 117.9 . . ? O1 C8 N2 119.0(4) . . ? O1 C8 C9 122.3(4) . . ? N2 C8 C9 118.7(4) . . ? C10 C9 C14 121.2(4) . . ? C10 C9 C8 119.2(4) . . ? C14 C9 C8 119.6(4) . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? O2 C11 C10 125.5(6) . . ? O2 C11 C12 114.5(5) . . ? C10 C11 C12 120.0(5) . . ? O3 C12 C13 118.6(5) . . ? O3 C12 C11 121.3(6) . . ? C13 C12 C11 120.0(5) . . ? O4 C13 C14 125.3(5) . . ? O4 C13 C12 114.9(5) . . ? C14 C13 C12 119.8(5) . . ? C13 C14 C9 119.5(5) . . ? C13 C14 H14A 120.3 . . ? C9 C14 H14A 120.3 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16A H16A 109.5 . . ? O3 C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? O3 C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? O3 C16B H16D 109.5 . . ? O3 C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? O3 C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O10 C21 C22 119.7(4) . . ? O10 C21 C26 122.1(4) . . ? C22 C21 C26 118.2(4) . . ? C21 C22 C23 121.5(5) . . ? C21 C22 H22A 119.2 . . ? C23 C22 H22A 119.2 . . ? C24 C23 C22 120.0(5) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C23 C24 C25 120.4(5) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C24 C25 C26 121.1(5) . . ? C24 C25 H25A 119.4 . . ? C26 C25 H25A 119.4 . . ? C25 C26 C21 118.6(4) . . ? C25 C26 C27 117.7(4) . . ? C21 C26 C27 123.7(4) . . ? N3 C27 C26 123.0(4) . . ? N3 C27 H27A 118.5 . . ? C26 C27 H27A 118.5 . . ? O6 C28 N4 118.2(4) . . ? O6 C28 C29 120.7(5) . . ? N4 C28 C29 121.1(5) . . ? O6 C28 C29A 129.6(4) . . ? N4 C28 C29A 111.8(4) . . ? C34 C29 C30 120.1(6) . . ? C34 C29 C28 122.1(6) . . ? C30 C29 C28 117.7(7) . . ? C31 C30 C29 121.3(7) . . ? C31 C30 H30A 119.4 . . ? C29 C30 H30A 119.4 . . ? C30 C31 C32 119.9(6) . . ? C30 C31 O7 124.6(6) . . ? C32 C31 O7 115.5(5) . . ? C31 C32 O8 119.9(5) . . ? C31 C32 C33 119.8(5) . . ? O8 C32 C33 120.1(5) . . ? O9 C33 C34 124.9(9) . . ? O9 C33 C32 115.6(5) . . ? C34 C33 C32 119.2(8) . . ? C29 C34 C33 119.6(9) . . ? C29 C34 H34A 120.2 . . ? C33 C34 H34A 120.2 . . ? O7 C35 H35A 109.5 . . ? O7 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O7 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O8 C36 H36A 109.5 . . ? O8 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O8 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O9 C37 H37A 109.5 . . ? O9 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O9 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34A C29A C30A 120.0 . . ? C34A C29A C28 126.9(3) . . ? C30A C29A C28 112.6(3) . . ? C29A C30A C31A 120.0 . . ? C29A C30A H30B 120.0 . . ? C31A C30A H30B 120.0 . . ? C30A C31A C32A 120.0 . . ? C30A C31A O7A 126.7(3) . . ? C32A C31A O7A 113.1(3) . . ? O8A C32A C33A 110.5(4) . . ? O8A C32A C31A 128.8(4) . . ? C33A C32A C31A 120.0 . . ? C32A C33A C34A 120.0 . . ? C32A C33A O9A 118.3(4) . . ? C34A C33A O9A 117.3(4) . . ? C29A C34A C33A 120.0 . . ? C29A C34A H34B 120.0 . . ? C33A C34A H34B 120.0 . . ? O7A C35A H35D 109.5 . . ? O7A C35A H35E 109.5 . . ? H35D C35A H35E 109.5 . . ? O7A C35A H35F 109.5 . . ? H35D C35A H35F 109.5 . . ? H35E C35A H35F 109.5 . . ? O8A C36A H36D 109.5 . . ? O8A C36A H36E 109.5 . . ? H36D C36A H36E 109.5 . . ? O8A C36A H36F 109.5 . . ? H36D C36A H36F 109.5 . . ? H36E C36A H36F 109.5 . . ? O9A C37A H37D 109.5 . . ? O9A C37A H37E 109.5 . . ? H37D C37A H37E 109.5 . . ? O9A C37A H37F 109.5 . . ? H37D C37A H37F 109.5 . . ? H37E C37A H37F 109.5 . . ? O13 N5 O11 117.9(5) . . ? O13 N5 O12 123.0(5) . . ? O11 N5 O12 119.1(6) . . ? C71 C72 C73 108.7 . . ? C74 C73 C72 109.2 . . ? C75 C74 C73 109.3 . . ? C75 C75 C74 171.4(4) 3_666 . ? C82 C81 C85 112.2 . . ? C81 C82 C83 99.2 . . ? C84 C83 C82 118.1 . . ? C83 C84 C85 101.2 . . ? C84 C85 C81 109.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O10 Fe1 O1 C8 98.7(3) . . . . ? O5 Fe1 O1 C8 -11.9(6) . . . . ? O6 Fe1 O1 C8 -101.7(3) . . . . ? N3 Fe1 O1 C8 -176.2(3) . . . . ? N1 Fe1 O1 C8 -4.7(3) . . . . ? O10 Fe1 O5 C1 -106.8(5) . . . . ? O6 Fe1 O5 C1 92.2(5) . . . . ? O1 Fe1 O5 C1 2.7(8) . . . . ? N3 Fe1 O5 C1 166.5(5) . . . . ? N1 Fe1 O5 C1 -4.3(5) . . . . ? O10 Fe1 O6 C28 -12.8(6) . . . . ? O5 Fe1 O6 C28 99.7(3) . . . . ? O1 Fe1 O6 C28 -101.0(3) . . . . ? N3 Fe1 O6 C28 -5.2(3) . . . . ? N1 Fe1 O6 C28 -175.6(3) . . . . ? O5 Fe1 O10 C21 -114.1(5) . . . . ? O6 Fe1 O10 C21 -2.6(8) . . . . ? O1 Fe1 O10 C21 85.3(5) . . . . ? N3 Fe1 O10 C21 -10.1(5) . . . . ? N1 Fe1 O10 C21 159.8(4) . . . . ? O10 Fe1 N1 C7 96.9(4) . . . . ? O5 Fe1 N1 C7 1.0(4) . . . . ? O6 Fe1 N1 C7 -89.2(4) . . . . ? O1 Fe1 N1 C7 -176.5(4) . . . . ? N3 Fe1 N1 C7 -135.0(6) . . . . ? O10 Fe1 N1 N2 -83.9(3) . . . . ? O5 Fe1 N1 N2 -179.8(3) . . . . ? O6 Fe1 N1 N2 90.0(3) . . . . ? O1 Fe1 N1 N2 2.7(3) . . . . ? N3 Fe1 N1 N2 44.2(7) . . . . ? C7 N1 N2 C8 178.6(4) . . . . ? Fe1 N1 N2 C8 -0.7(5) . . . . ? O10 Fe1 N3 C27 6.5(4) . . . . ? O5 Fe1 N3 C27 102.4(4) . . . . ? O6 Fe1 N3 C27 -170.9(4) . . . . ? O1 Fe1 N3 C27 -83.3(4) . . . . ? N1 Fe1 N3 C27 -123.2(6) . . . . ? O10 Fe1 N3 N4 -177.1(3) . . . . ? O5 Fe1 N3 N4 -81.2(3) . . . . ? O6 Fe1 N3 N4 5.5(3) . . . . ? O1 Fe1 N3 N4 93.1(3) . . . . ? N1 Fe1 N3 N4 53.2(7) . . . . ? C27 N3 N4 C28 171.2(4) . . . . ? Fe1 N3 N4 C28 -5.7(5) . . . . ? Fe1 O5 C1 C2 -172.5(4) . . . . ? Fe1 O5 C1 C6 4.9(8) . . . . ? O5 C1 C2 C3 178.7(5) . . . . ? C6 C1 C2 C3 1.2(8) . . . . ? C1 C2 C3 C4 -0.7(10) . . . . ? C2 C3 C4 C5 0.2(10) . . . . ? C3 C4 C5 C6 -0.2(9) . . . . ? C4 C5 C6 C1 0.7(8) . . . . ? C4 C5 C6 C7 -177.0(5) . . . . ? O5 C1 C6 C5 -178.6(5) . . . . ? C2 C1 C6 C5 -1.1(7) . . . . ? O5 C1 C6 C7 -1.0(8) . . . . ? C2 C1 C6 C7 176.4(5) . . . . ? N2 N1 C7 C6 -177.9(4) . . . . ? Fe1 N1 C7 C6 1.3(7) . . . . ? C5 C6 C7 N1 175.8(5) . . . . ? C1 C6 C7 N1 -1.8(8) . . . . ? Fe1 O1 C8 N2 6.1(5) . . . . ? Fe1 O1 C8 C9 -172.3(3) . . . . ? N1 N2 C8 O1 -3.6(6) . . . . ? N1 N2 C8 C9 174.9(4) . . . . ? O1 C8 C9 C10 -27.2(6) . . . . ? N2 C8 C9 C10 154.3(4) . . . . ? O1 C8 C9 C14 149.7(4) . . . . ? N2 C8 C9 C14 -28.8(6) . . . . ? C14 C9 C10 C11 1.3(7) . . . . ? C8 C9 C10 C11 178.1(4) . . . . ? C15 O2 C11 C10 -6.5(10) . . . . ? C15 O2 C11 C12 174.0(7) . . . . ? C9 C10 C11 O2 179.1(5) . . . . ? C9 C10 C11 C12 -1.3(8) . . . . ? C16B O3 C12 C13 127.8(12) . . . . ? C16A O3 C12 C13 80.2(10) . . . . ? C16B O3 C12 C11 -55.6(13) . . . . ? C16A O3 C12 C11 -103.2(10) . . . . ? O2 C11 C12 O3 4.0(8) . . . . ? C10 C11 C12 O3 -175.6(5) . . . . ? O2 C11 C12 C13 -179.4(5) . . . . ? C10 C11 C12 C13 1.0(8) . . . . ? C17 O4 C13 C14 5.5(7) . . . . ? C17 O4 C13 C12 -174.6(5) . . . . ? O3 C12 C13 O4 -3.8(7) . . . . ? C11 C12 C13 O4 179.6(5) . . . . ? O3 C12 C13 C14 176.2(5) . . . . ? C11 C12 C13 C14 -0.5(8) . . . . ? O4 C13 C14 C9 -179.7(4) . . . . ? C12 C13 C14 C9 0.4(7) . . . . ? C10 C9 C14 C13 -0.8(7) . . . . ? C8 C9 C14 C13 -177.7(4) . . . . ? Fe1 O10 C21 C22 -171.1(4) . . . . ? Fe1 O10 C21 C26 9.3(7) . . . . ? O10 C21 C22 C23 -179.0(5) . . . . ? C26 C21 C22 C23 0.6(8) . . . . ? C21 C22 C23 C24 1.5(9) . . . . ? C22 C23 C24 C25 -2.2(9) . . . . ? C23 C24 C25 C26 0.7(8) . . . . ? C24 C25 C26 C21 1.4(8) . . . . ? C24 C25 C26 C27 180.0(5) . . . . ? O10 C21 C26 C25 177.6(4) . . . . ? C22 C21 C26 C25 -2.0(7) . . . . ? O10 C21 C26 C27 -0.9(7) . . . . ? C22 C21 C26 C27 179.5(5) . . . . ? N4 N3 C27 C26 -178.9(4) . . . . ? Fe1 N3 C27 C26 -2.6(7) . . . . ? C25 C26 C27 N3 179.7(4) . . . . ? C21 C26 C27 N3 -1.8(7) . . . . ? Fe1 O6 C28 N4 3.7(5) . . . . ? Fe1 O6 C28 C29 -177.5(4) . . . . ? Fe1 O6 C28 C29A -168.5(4) . . . . ? N3 N4 C28 O6 1.4(6) . . . . ? N3 N4 C28 C29 -177.3(5) . . . . ? N3 N4 C28 C29A 175.0(4) . . . . ? O6 C28 C29 C34 -177.5(5) . . . . ? N4 C28 C29 C34 1.3(9) . . . . ? C29A C28 C29 C34 39.5(18) . . . . ? O6 C28 C29 C30 -0.6(9) . . . . ? N4 C28 C29 C30 178.2(6) . . . . ? C29A C28 C29 C30 -144(2) . . . . ? C34 C29 C30 C31 3.1(12) . . . . ? C28 C29 C30 C31 -173.8(7) . . . . ? C29 C30 C31 C32 -0.4(12) . . . . ? C29 C30 C31 O7 179.7(7) . . . . ? C35 O7 C31 C30 -0.2(11) . . . . ? C35 O7 C31 C32 179.8(6) . . . . ? C30 C31 C32 O8 172.2(7) . . . . ? O7 C31 C32 O8 -7.9(9) . . . . ? C30 C31 C32 C33 -3.5(10) . . . . ? O7 C31 C32 C33 176.4(6) . . . . ? C36 O8 C32 C31 106.8(7) . . . . ? C36 O8 C32 C33 -77.5(8) . . . . ? C37 O9 C33 C34 -9.3(10) . . . . ? C37 O9 C33 C32 176.9(5) . . . . ? C31 C32 C33 O9 179.0(6) . . . . ? O8 C32 C33 O9 3.3(9) . . . . ? C31 C32 C33 C34 4.8(9) . . . . ? O8 C32 C33 C34 -171.0(5) . . . . ? C30 C29 C34 C33 -1.8(10) . . . . ? C28 C29 C34 C33 175.0(6) . . . . ? O9 C33 C34 C29 -175.7(6) . . . . ? C32 C33 C34 C29 -2.0(9) . . . . ? O6 C28 C29A C34A -171.1(3) . . . . ? N4 C28 C29A C34A 16.3(5) . . . . ? C29 C28 C29A C34A -129.0(19) . . . . ? O6 C28 C29A C30A 1.2(6) . . . . ? N4 C28 C29A C30A -171.4(3) . . . . ? C29 C28 C29A C30A 43.3(18) . . . . ? C34A C29A C30A C31A 0.0 . . . . ? C28 C29A C30A C31A -172.8(3) . . . . ? C29A C30A C31A C32A 0.0 . . . . ? C29A C30A C31A O7A -174.6(4) . . . . ? C35A O7A C31A C30A 2.5(7) . . . . ? C35A O7A C31A C32A -172.4(3) . . . . ? C36A O8A C32A C33A -173.6(4) . . . . ? C36A O8A C32A C31A 15.7(8) . . . . ? C30A C31A C32A O8A 169.9(5) . . . . ? O7A C31A C32A O8A -14.88(17) . . . . ? C30A C31A C32A C33A 0.0 . . . . ? O7A C31A C32A C33A 175.2(3) . . . . ? O8A C32A C33A C34A -171.6(4) . . . . ? C31A C32A C33A C34A 0.0 . . . . ? O8A C32A C33A O9A 32.74(19) . . . . ? C31A C32A C33A O9A -155.7(4) . . . . ? C37A O9A C33A C32A -169.4(3) . . . . ? C37A O9A C33A C34A 34.2(6) . . . . ? C30A C29A C34A C33A 0.0 . . . . ? C28 C29A C34A C33A 171.7(4) . . . . ? C32A C33A C34A C29A 0.0 . . . . ? O9A C33A C34A C29A 155.9(4) . . . . ? C71 C72 C73 C74 -167.7 . . . . ? C72 C73 C74 C75 179.2 . . . . ? C85 C81 C82 C83 1.0 . . . . ? C81 C82 C83 C84 1.7 . . . . ? C82 C83 C84 C85 -3.6 . . . . ? C83 C84 C85 C81 3.8 . . . . ? C82 C81 C85 C84 -3.2 . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O11 0.86 2.16 2.804(5) 131.8 1_556 N2 H2A O13 0.86 2.41 3.253(6) 167.3 1_556 N2 H2A N5 0.86 2.65 3.455(5) 155.9 1_556 N4 H3A O12 0.86 1.95 2.800(5) 170.0 . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.72 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.080 _refine_diff_density_min -0.673 _refine_diff_density_rms 0.084 #===END data_dp220 _database_code_depnum_ccdc_archive 'CCDC 643170' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SBH(m-OMe) _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N2 O3' _chemical_formula_sum 'C15 H14 N2 O3' _chemical_formula_weight 270.28 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' _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 11.4645(9) _cell_length_b 13.6942(11) _cell_length_c 8.5467(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.025(4) _cell_angle_gamma 90.00 _cell_volume 1341.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2411 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 25.03 _exptl_crystal_description Needles _exptl_crystal_colour 'Colorless ' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9906 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2722 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2722 _reflns_number_gt 1937 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex II 2.0 Rev.2 (Bruker, 2005)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT 7.12A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0574P)^2^+0.0317P] 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 2722 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1122 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.78370(10) 0.15968(7) 0.33728(10) 0.0498(3) Uani 1 1 d . . . O2 O 0.88759(12) -0.13938(9) 0.68041(16) 0.0744(4) Uani 1 1 d . . . O3 O 0.57823(10) 0.39412(8) 0.19707(11) 0.0585(3) Uani 1 1 d . . . H1A H 0.6246 0.3569 0.2466 0.070 Uiso 1 1 calc R . . N1 N 0.72247(11) 0.34123(9) 0.43141(12) 0.0400(3) Uani 1 1 d . . . N2 N 0.78467(11) 0.27586(9) 0.52523(12) 0.0417(3) Uani 1 1 d . . . H2A H 0.8074 0.2927 0.6209 0.050 Uiso 1 1 calc R . . C1 C 0.57611(13) 0.48217(11) 0.26886(16) 0.0429(4) Uani 1 1 d . . . C2 C 0.50647(15) 0.55450(12) 0.20261(18) 0.0541(4) Uani 1 1 d . . . H2B H 0.4609 0.5411 0.1101 0.065 Uiso 1 1 calc R . . C3 C 0.50255(15) 0.64536(13) 0.2693(2) 0.0579(5) Uani 1 1 d . . . H3B H 0.4555 0.6948 0.2212 0.070 Uiso 1 1 calc R . . C4 C 0.56609(16) 0.66588(12) 0.4055(2) 0.0590(5) Uani 1 1 d . . . H4A H 0.5639 0.7292 0.4508 0.071 Uiso 1 1 calc R . . C5 C 0.63253(14) 0.59325(12) 0.47443(18) 0.0511(4) Uani 1 1 d . . . H5A H 0.6743 0.6066 0.5700 0.061 Uiso 1 1 calc R . . C6 C 0.64054(12) 0.50051(10) 0.40848(15) 0.0388(3) Uani 1 1 d . . . C7 C 0.70930(13) 0.42621(11) 0.48935(15) 0.0408(4) Uani 1 1 d . . . H7A H 0.7456 0.4411 0.5881 0.049 Uiso 1 1 calc R . . C8 C 0.81039(13) 0.18695(10) 0.47103(14) 0.0369(3) Uani 1 1 d . . . C9 C 0.87387(12) 0.12163(10) 0.58506(14) 0.0366(3) Uani 1 1 d . . . C10 C 0.85020(13) 0.02247(11) 0.57462(16) 0.0421(4) Uani 1 1 d . . . H10A H 0.7960 -0.0014 0.4971 0.051 Uiso 1 1 calc R . . C11 C 0.90576(14) -0.04125(11) 0.67723(17) 0.0485(4) Uani 1 1 d . . . C12 C 0.98674(15) -0.00622(13) 0.78778(18) 0.0566(5) Uani 1 1 d . . . H12A H 1.0257 -0.0503 0.8578 0.068 Uiso 1 1 calc R . . C13 C 1.01062(15) 0.09104(13) 0.79630(18) 0.0558(5) Uani 1 1 d . . . H13A H 1.0666 0.1143 0.8721 0.067 Uiso 1 1 calc R . . C14 C 0.95437(14) 0.15664(11) 0.69591(16) 0.0451(4) Uani 1 1 d . . . H14A H 0.9708 0.2245 0.7030 0.054 Uiso 1 1 calc R . . C15 C 0.79941(19) -0.17769(14) 0.5778(3) 0.0869(7) Uani 1 1 d . . . H15C H 0.7950 -0.2486 0.5912 0.130 Uiso 1 1 calc R . . H15D H 0.8180 -0.1626 0.4694 0.130 Uiso 1 1 calc R . . H15A H 0.7242 -0.1483 0.6016 0.130 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0710(8) 0.0462(7) 0.0316(5) -0.0009(4) -0.0089(5) 0.0012(5) O2 0.0764(9) 0.0400(7) 0.1062(10) 0.0180(7) -0.0036(8) 0.0034(6) O3 0.0771(8) 0.0500(7) 0.0472(6) -0.0063(5) -0.0147(5) 0.0125(6) N1 0.0469(8) 0.0384(7) 0.0346(5) 0.0060(5) -0.0011(5) 0.0049(6) N2 0.0559(8) 0.0393(7) 0.0293(5) 0.0025(5) -0.0075(5) 0.0074(6) C1 0.0467(9) 0.0424(9) 0.0398(7) 0.0034(6) 0.0039(6) 0.0039(7) C2 0.0566(11) 0.0591(11) 0.0464(8) 0.0074(7) -0.0022(8) 0.0123(8) C3 0.0564(11) 0.0510(11) 0.0668(10) 0.0148(8) 0.0078(9) 0.0168(9) C4 0.0616(12) 0.0392(10) 0.0766(11) -0.0009(8) 0.0096(9) 0.0061(8) C5 0.0531(10) 0.0428(9) 0.0572(9) -0.0020(7) -0.0012(8) -0.0005(8) C6 0.0390(8) 0.0363(8) 0.0413(7) 0.0036(6) 0.0032(6) -0.0005(6) C7 0.0445(9) 0.0398(9) 0.0380(7) 0.0020(6) -0.0017(6) -0.0027(7) C8 0.0425(9) 0.0369(8) 0.0313(6) 0.0016(6) 0.0002(6) -0.0029(6) C9 0.0399(8) 0.0381(8) 0.0320(6) 0.0007(6) 0.0025(6) 0.0017(7) C10 0.0420(9) 0.0418(9) 0.0424(7) 0.0003(6) 0.0002(6) 0.0008(7) C11 0.0516(10) 0.0387(9) 0.0556(9) 0.0098(7) 0.0078(8) 0.0064(7) C12 0.0574(11) 0.0589(12) 0.0531(9) 0.0146(8) -0.0040(8) 0.0144(9) C13 0.0514(10) 0.0654(12) 0.0496(8) 0.0018(8) -0.0143(7) 0.0049(9) C14 0.0482(10) 0.0439(9) 0.0428(7) 0.0001(6) -0.0038(7) 0.0012(7) C15 0.0739(15) 0.0432(12) 0.143(2) 0.0010(12) 0.0003(14) -0.0085(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 C8 1.2309(15) . ? O2 C11 1.3604(19) . ? O2 C15 1.416(2) . ? O3 C1 1.3535(18) . ? O3 H1A 0.8400 . ? N1 C7 1.2758(17) . ? N1 N2 1.3829(15) . ? N2 C8 1.3393(17) . ? N2 H2A 0.8800 . ? C1 C2 1.381(2) . ? C1 C6 1.4037(19) . ? C2 C3 1.370(2) . ? C2 H2B 0.9500 . ? C3 C4 1.380(2) . ? C3 H3B 0.9500 . ? C4 C5 1.373(2) . ? C4 H4A 0.9500 . ? C5 C6 1.394(2) . ? C5 H5A 0.9500 . ? C6 C7 1.4478(19) . ? C7 H7A 0.9500 . ? C8 C9 1.4932(18) . ? C9 C14 1.3846(19) . ? C9 C10 1.387(2) . ? C10 C11 1.3772(19) . ? C10 H10A 0.9500 . ? C11 C12 1.387(2) . ? C12 C13 1.361(2) . ? C12 H12A 0.9500 . ? C13 C14 1.386(2) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15C 0.9800 . ? C15 H15D 0.9800 . ? C15 H15A 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 C11 O2 C15 117.39(13) . . ? C1 O3 H1A 109.5 . . ? C7 N1 N2 115.54(11) . . ? C8 N2 N1 120.22(10) . . ? C8 N2 H2A 119.9 . . ? N1 N2 H2A 119.9 . . ? O3 C1 C2 118.19(13) . . ? O3 C1 C6 121.84(13) . . ? C2 C1 C6 119.96(14) . . ? C3 C2 C1 120.52(15) . . ? C3 C2 H2B 119.7 . . ? C1 C2 H2B 119.7 . . ? C2 C3 C4 120.78(15) . . ? C2 C3 H3B 119.6 . . ? C4 C3 H3B 119.6 . . ? C5 C4 C3 118.86(16) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 122.01(15) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C5 C6 C1 117.82(13) . . ? C5 C6 C7 119.33(13) . . ? C1 C6 C7 122.77(13) . . ? N1 C7 C6 121.71(13) . . ? N1 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? O1 C8 N2 123.13(12) . . ? O1 C8 C9 121.59(13) . . ? N2 C8 C9 115.28(11) . . ? C14 C9 C10 120.47(13) . . ? C14 C9 C8 122.47(13) . . ? C10 C9 C8 117.05(12) . . ? C11 C10 C9 119.62(13) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? O2 C11 C10 124.81(14) . . ? O2 C11 C12 115.30(13) . . ? C10 C11 C12 119.89(15) . . ? C13 C12 C11 120.22(14) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C12 C13 C14 120.86(14) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C9 C14 C13 118.92(14) . . ? C9 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? O2 C15 H15C 109.5 . . ? O2 C15 H15D 109.5 . . ? H15C C15 H15D 109.5 . . ? O2 C15 H15A 109.5 . . ? H15C C15 H15A 109.5 . . ? H15D C15 H15A 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 C7 N1 N2 C8 -175.33(13) . . . . ? O3 C1 C2 C3 -179.01(15) . . . . ? C6 C1 C2 C3 2.1(2) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 2.0(3) . . . . ? C4 C5 C6 C1 -1.2(2) . . . . ? C4 C5 C6 C7 -178.16(15) . . . . ? O3 C1 C6 C5 -179.68(14) . . . . ? C2 C1 C6 C5 -0.9(2) . . . . ? O3 C1 C6 C7 -2.8(2) . . . . ? C2 C1 C6 C7 175.96(14) . . . . ? N2 N1 C7 C6 -176.42(13) . . . . ? C5 C6 C7 N1 -177.67(15) . . . . ? C1 C6 C7 N1 5.5(2) . . . . ? N1 N2 C8 O1 1.9(2) . . . . ? N1 N2 C8 C9 -177.79(12) . . . . ? O1 C8 C9 C14 146.17(15) . . . . ? N2 C8 C9 C14 -34.2(2) . . . . ? O1 C8 C9 C10 -32.9(2) . . . . ? N2 C8 C9 C10 146.71(13) . . . . ? C14 C9 C10 C11 1.2(2) . . . . ? C8 C9 C10 C11 -179.70(13) . . . . ? C15 O2 C11 C10 -4.5(2) . . . . ? C15 O2 C11 C12 175.36(17) . . . . ? C9 C10 C11 O2 178.43(14) . . . . ? C9 C10 C11 C12 -1.4(2) . . . . ? O2 C11 C12 C13 -179.19(16) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C10 C9 C14 C13 -0.1(2) . . . . ? C8 C9 C14 C13 -179.22(14) . . . . ? C12 C13 C14 C9 -0.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1A N1 0.84 1.92 2.6526(14) 145.6 . N2 H2A O1 0.88 1.99 2.8097(14) 154.7 4_566 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.153 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.035 #===END data_dp243 _database_code_depnum_ccdc_archive 'CCDC 643171' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BSBH(m-OMe) _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 B N2 O4' _chemical_formula_sum 'C21 H25 B N2 O4' _chemical_formula_weight 380.24 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 Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 17.8735(16) _cell_length_b 12.7925(10) _cell_length_c 9.0933(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2079.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2848 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 22.46 _exptl_crystal_description Needles _exptl_crystal_colour 'Colorless ' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12932 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3464 _reflns_number_gt 2534 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex II 2.0 Rev.2 (Bruker, 2005)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT 7.12A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0612P)^2^+0.2170P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(14) _refine_ls_number_reflns 3464 _refine_ls_number_parameters 258 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 B1 B 0.41924(17) 0.3030(2) 0.0757(3) 0.0458(7) Uani 1 1 d . . . O1 O 0.18614(11) 0.63799(12) 0.48468(19) 0.0537(5) Uani 1 1 d . . . O2 O 0.06414(14) 0.98894(16) 0.3637(3) 0.0853(7) Uani 1 1 d . . . O3 O 0.41885(11) 0.39808(14) 0.0114(2) 0.0671(6) Uani 1 1 d . A 1 O4 O 0.47054(13) 0.23822(14) 0.0171(3) 0.0801(7) Uani 1 1 d . A 1 N1 N 0.26394(11) 0.49866(15) 0.3253(2) 0.0434(5) Uani 1 1 d . . . N2 N 0.24959(12) 0.59873(13) 0.2757(2) 0.0436(5) Uani 1 1 d . . . H2A H 0.2653 0.6189 0.1909 0.052 Uiso 1 1 calc R . . C1 C 0.36826(13) 0.26867(18) 0.2060(3) 0.0429(6) Uani 1 1 d . A . C2 C 0.37562(16) 0.1644(2) 0.2512(3) 0.0569(7) Uani 1 1 d . . . H2B H 0.4104 0.1219 0.2041 0.068 Uiso 1 1 calc R A . C3 C 0.33303(18) 0.1227(2) 0.3628(4) 0.0664(8) Uani 1 1 d . A . H3A H 0.3381 0.0526 0.3880 0.080 Uiso 1 1 calc R . . C4 C 0.28299(16) 0.1851(2) 0.4370(4) 0.0645(8) Uani 1 1 d . . . H4A H 0.2552 0.1581 0.5146 0.077 Uiso 1 1 calc R A . C5 C 0.27442(14) 0.28800(19) 0.3954(3) 0.0519(7) Uani 1 1 d . A . H5A H 0.2402 0.3299 0.4451 0.062 Uiso 1 1 calc R . . C6 C 0.31586(12) 0.33042(18) 0.2807(3) 0.0401(5) Uani 1 1 d . . . C7 C 0.30093(13) 0.44051(17) 0.2382(3) 0.0406(5) Uani 1 1 d . A . H7A H 0.3184 0.4666 0.1491 0.049 Uiso 1 1 calc R . . C8 C 0.21017(13) 0.66463(17) 0.3634(3) 0.0410(5) Uani 1 1 d . . . C9 C 0.19714(13) 0.77214(18) 0.3050(3) 0.0419(5) Uani 1 1 d . . . C10 C 0.13658(14) 0.82727(19) 0.3629(3) 0.0480(6) Uani 1 1 d . . . H10A H 0.1060 0.7963 0.4332 0.058 Uiso 1 1 calc R . . C11 C 0.12207(17) 0.9283(2) 0.3155(3) 0.0575(7) Uani 1 1 d . . . C12 C 0.16753(19) 0.9738(2) 0.2102(4) 0.0699(9) Uani 1 1 d . . . H12A H 0.1575 1.0413 0.1778 0.084 Uiso 1 1 calc R . . C13 C 0.22726(18) 0.9201(2) 0.1534(4) 0.0664(9) Uani 1 1 d . . . H13A H 0.2575 0.9515 0.0829 0.080 Uiso 1 1 calc R . . C14 C 0.24299(16) 0.81872(18) 0.2006(3) 0.0519(7) Uani 1 1 d . . . H14A H 0.2838 0.7827 0.1625 0.062 Uiso 1 1 calc R . . C15 C 0.0252(2) 0.9567(2) 0.4888(4) 0.0758(9) Uani 1 1 d . . . H15A H -0.0079 1.0114 0.5201 0.114 Uiso 1 1 calc R . . H15B H 0.0602 0.9413 0.5661 0.114 Uiso 1 1 calc R . . H15C H -0.0033 0.8952 0.4663 0.114 Uiso 1 1 calc R . . C16 C 0.46605(16) 0.3908(3) -0.1210(4) 0.0690(8) Uani 1 1 d . A 1 C17 C 0.51707(18) 0.2998(2) -0.0829(4) 0.0719(9) Uani 1 1 d . A 1 C18 C 0.4126(2) 0.3642(5) -0.2504(5) 0.140(2) Uani 1 1 d . A 1 H18A H 0.3896 0.2975 -0.2330 0.210 Uiso 1 1 calc R A 1 H18B H 0.4405 0.3617 -0.3405 0.210 Uiso 1 1 calc R A 1 H18C H 0.3746 0.4170 -0.2577 0.210 Uiso 1 1 calc R A 1 C19 C 0.5019(3) 0.4959(3) -0.1459(5) 0.1003(13) Uani 1 1 d . A 1 H19A H 0.5298 0.5156 -0.0601 0.151 Uiso 1 1 calc R A 1 H19B H 0.4637 0.5471 -0.1646 0.151 Uiso 1 1 calc R A 1 H19C H 0.5349 0.4920 -0.2290 0.151 Uiso 1 1 calc R A 1 C20 C 0.5425(3) 0.2296(4) -0.2064(5) 0.1217(17) Uani 1 1 d . A 1 H20A H 0.4997 0.1989 -0.2533 0.182 Uiso 1 1 calc R A 1 H20B H 0.5739 0.1752 -0.1675 0.182 Uiso 1 1 calc R A 1 H20C H 0.5702 0.2698 -0.2769 0.182 Uiso 1 1 calc R A 1 C21 C 0.58635(19) 0.3362(4) 0.0031(5) 0.1080(14) Uani 1 1 d . A 1 H21A H 0.5716 0.3860 0.0766 0.162 Uiso 1 1 calc R A 1 H21B H 0.6213 0.3682 -0.0632 0.162 Uiso 1 1 calc R A 1 H21C H 0.6094 0.2771 0.0498 0.162 Uiso 1 1 calc R 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 B1 0.0475(15) 0.0504(16) 0.0395(15) -0.0008(12) 0.0012(13) -0.0010(14) O1 0.0774(12) 0.0470(9) 0.0369(9) 0.0094(8) 0.0070(9) 0.0089(9) O2 0.1050(16) 0.0692(14) 0.0818(16) 0.0182(12) 0.0231(15) 0.0407(12) O3 0.0743(13) 0.0642(11) 0.0628(13) 0.0176(10) 0.0297(11) 0.0148(10) O4 0.0958(15) 0.0598(12) 0.0846(15) 0.0074(12) 0.0475(14) 0.0156(11) N1 0.0505(10) 0.0386(10) 0.0411(11) 0.0111(9) 0.0048(10) 0.0068(8) N2 0.0566(11) 0.0381(10) 0.0361(11) 0.0117(8) 0.0047(9) 0.0057(9) C1 0.0464(13) 0.0427(13) 0.0396(13) 0.0040(11) 0.0008(11) 0.0030(10) C2 0.0652(17) 0.0491(15) 0.0565(18) 0.0063(13) 0.0088(14) 0.0163(12) C3 0.0848(19) 0.0415(14) 0.073(2) 0.0205(15) 0.0154(18) 0.0102(14) C4 0.0720(18) 0.0587(17) 0.0629(19) 0.0264(15) 0.0221(16) 0.0100(14) C5 0.0543(14) 0.0496(14) 0.0518(17) 0.0155(13) 0.0152(13) 0.0123(11) C6 0.0402(12) 0.0407(12) 0.0394(13) 0.0062(10) -0.0004(11) 0.0015(10) C7 0.0434(12) 0.0416(12) 0.0368(12) 0.0083(10) 0.0038(11) 0.0001(10) C8 0.0502(13) 0.0404(13) 0.0323(12) 0.0033(10) -0.0043(12) 0.0007(10) C9 0.0511(13) 0.0395(13) 0.0351(12) 0.0037(10) -0.0056(11) 0.0009(10) C10 0.0590(14) 0.0471(14) 0.0378(13) 0.0087(11) -0.0003(13) 0.0047(11) C11 0.0707(17) 0.0519(16) 0.0499(16) 0.0066(13) 0.0013(14) 0.0179(13) C12 0.095(2) 0.0465(16) 0.068(2) 0.0215(15) 0.0104(19) 0.0180(16) C13 0.079(2) 0.0506(16) 0.070(2) 0.0189(15) 0.0150(17) -0.0002(15) C14 0.0568(15) 0.0445(13) 0.0544(17) 0.0076(12) 0.0094(14) 0.0027(12) C15 0.081(2) 0.0704(19) 0.076(2) -0.0045(19) 0.0153(19) 0.0130(16) C16 0.0648(17) 0.093(2) 0.0489(16) 0.0125(16) 0.0227(16) 0.0038(16) C17 0.077(2) 0.0751(19) 0.064(2) 0.0026(16) 0.0304(18) 0.0051(16) C18 0.081(3) 0.288(7) 0.052(2) 0.034(3) -0.005(2) -0.027(4) C19 0.116(3) 0.093(3) 0.092(3) 0.034(2) 0.044(3) 0.002(2) C20 0.137(4) 0.114(3) 0.113(4) -0.027(3) 0.070(3) 0.003(3) C21 0.0563(18) 0.182(4) 0.086(3) 0.025(3) 0.000(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O4 1.346(3) . ? B1 O3 1.350(3) . ? B1 C1 1.557(4) . ? O1 C8 1.231(3) . ? O2 C11 1.366(3) . ? O2 C15 1.395(4) . ? O3 C16 1.473(3) . ? O4 C17 1.463(4) . ? N1 C7 1.272(3) . ? N1 N2 1.381(2) . ? N2 C8 1.358(3) . ? N2 H2A 0.8600 . ? C1 C6 1.401(3) . ? C1 C2 1.402(3) . ? C2 C3 1.376(4) . ? C2 H2B 0.9300 . ? C3 C4 1.376(4) . ? C3 H3A 0.9300 . ? C4 C5 1.377(4) . ? C4 H4A 0.9300 . ? C5 C6 1.390(3) . ? C5 H5A 0.9300 . ? C6 C7 1.485(3) . ? C7 H7A 0.9300 . ? C8 C9 1.493(3) . ? C9 C14 1.389(4) . ? C9 C10 1.395(3) . ? C10 C11 1.387(3) . ? C10 H10A 0.9300 . ? C11 C12 1.384(4) . ? C12 C13 1.371(4) . ? C12 H12A 0.9300 . ? C13 C14 1.395(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C19 1.507(5) . ? C16 C17 1.518(4) . ? C16 C18 1.554(5) . ? C17 C20 1.508(5) . ? C17 C21 1.537(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 O4 B1 O3 112.7(2) . . ? O4 B1 C1 121.8(2) . . ? O3 B1 C1 125.5(2) . . ? C11 O2 C15 118.1(2) . . ? B1 O3 C16 107.1(2) . . ? B1 O4 C17 107.6(2) . . ? C7 N1 N2 115.81(19) . . ? C8 N2 N1 118.69(19) . . ? C8 N2 H2A 120.7 . . ? N1 N2 H2A 120.7 . . ? C6 C1 C2 117.2(2) . . ? C6 C1 B1 126.9(2) . . ? C2 C1 B1 115.9(2) . . ? C3 C2 C1 122.2(2) . . ? C3 C2 H2B 118.9 . . ? C1 C2 H2B 118.9 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C6 C1 120.0(2) . . ? C5 C6 C7 118.0(2) . . ? C1 C6 C7 121.9(2) . . ? N1 C7 C6 119.1(2) . . ? N1 C7 H7A 120.5 . . ? C6 C7 H7A 120.5 . . ? O1 C8 N2 122.4(2) . . ? O1 C8 C9 121.3(2) . . ? N2 C8 C9 116.4(2) . . ? C14 C9 C10 119.9(2) . . ? C14 C9 C8 123.1(2) . . ? C10 C9 C8 116.9(2) . . ? C11 C10 C9 119.9(2) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? O2 C11 C12 115.4(2) . . ? O2 C11 C10 124.8(3) . . ? C12 C11 C10 119.8(3) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C9 C14 C13 119.4(3) . . ? C9 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 C19 108.1(3) . . ? O3 C16 C17 101.9(2) . . ? C19 C16 C17 117.6(3) . . ? O3 C16 C18 106.3(2) . . ? C19 C16 C18 110.0(4) . . ? C17 C16 C18 112.0(4) . . ? O4 C17 C20 108.3(3) . . ? O4 C17 C16 102.3(2) . . ? C20 C17 C16 117.9(3) . . ? O4 C17 C21 107.7(3) . . ? C20 C17 C21 108.4(3) . . ? C16 C17 C21 111.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 B1 O3 C16 10.5(3) . . . . ? C1 B1 O3 C16 -170.7(3) . . . . ? O3 B1 O4 C17 8.8(4) . . . . ? C1 B1 O4 C17 -170.0(3) . . . . ? C7 N1 N2 C8 179.8(2) . . . . ? O4 B1 C1 C6 176.5(3) . . . . ? O3 B1 C1 C6 -2.2(4) . . . . ? O4 B1 C1 C2 -4.2(4) . . . . ? O3 B1 C1 C2 177.1(3) . . . . ? C6 C1 C2 C3 0.8(4) . . . . ? B1 C1 C2 C3 -178.6(3) . . . . ? C1 C2 C3 C4 -2.2(5) . . . . ? C2 C3 C4 C5 2.0(5) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C4 C5 C6 C7 177.3(3) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? B1 C1 C6 C5 180.0(3) . . . . ? C2 C1 C6 C7 -177.3(2) . . . . ? B1 C1 C6 C7 2.0(4) . . . . ? N2 N1 C7 C6 -177.4(2) . . . . ? C5 C6 C7 N1 15.1(3) . . . . ? C1 C6 C7 N1 -166.8(2) . . . . ? N1 N2 C8 O1 -0.8(3) . . . . ? N1 N2 C8 C9 179.27(19) . . . . ? O1 C8 C9 C14 155.9(2) . . . . ? N2 C8 C9 C14 -24.2(3) . . . . ? O1 C8 C9 C10 -22.6(3) . . . . ? N2 C8 C9 C10 157.3(2) . . . . ? C14 C9 C10 C11 0.3(4) . . . . ? C8 C9 C10 C11 178.8(2) . . . . ? C15 O2 C11 C12 -167.7(3) . . . . ? C15 O2 C11 C10 13.2(5) . . . . ? C9 C10 C11 O2 179.5(3) . . . . ? C9 C10 C11 C12 0.4(4) . . . . ? O2 C11 C12 C13 -179.8(3) . . . . ? C10 C11 C12 C13 -0.6(5) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C10 C9 C14 C13 -0.8(4) . . . . ? C8 C9 C14 C13 -179.2(3) . . . . ? C12 C13 C14 C9 0.5(5) . . . . ? B1 O3 C16 C19 -148.7(3) . . . . ? B1 O3 C16 C17 -24.2(3) . . . . ? B1 O3 C16 C18 93.2(4) . . . . ? B1 O4 C17 C20 -148.6(3) . . . . ? B1 O4 C17 C16 -23.4(3) . . . . ? B1 O4 C17 C21 94.3(3) . . . . ? O3 C16 C17 O4 28.1(3) . . . . ? C19 C16 C17 O4 145.9(3) . . . . ? C18 C16 C17 O4 -85.2(3) . . . . ? O3 C16 C17 C20 146.7(3) . . . . ? C19 C16 C17 C20 -95.5(4) . . . . ? C18 C16 C17 C20 33.4(4) . . . . ? O3 C16 C17 C21 -86.8(3) . . . . ? C19 C16 C17 C21 31.0(4) . . . . ? C18 C16 C17 C21 159.9(3) . . . . ? 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 N2 H2A O1 0.86 2.08 2.928(3) 168.3 4_554 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.164 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.029 #===END data_dp235 _database_code_depnum_ccdc_archive 'CCDC 643172' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SBH(m-OEt) _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N2 O3' _chemical_formula_sum 'C16 H16 N2 O3' _chemical_formula_weight 284.31 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' _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 11.5979(3) _cell_length_b 14.0704(3) _cell_length_c 9.4947(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.1330(10) _cell_angle_gamma 90.00 _cell_volume 1454.74(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 649 _cell_measurement_theta_min 3.69 _cell_measurement_theta_max 25.42 _exptl_crystal_description Needles _exptl_crystal_colour 'Colorless ' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9820 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2985 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2985 _reflns_number_gt 1954 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex II 2.0 Rev.2 (Bruker, 2005)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT 7.12A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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. The hydroxy hydrogen, O1-H1A, and the imine hydrogen, N1-H1B, were found on the difference map. The occupancy at the two sites is 50% each. The hydrogen was modeled in this way, because localizing the hydrogen on the hydroxy group resulted with high thermal parameter at the hydrogen site. Since both sites were found on the difference map, the structure was refined with equal population at those 2 sites. ; _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^)+(0.0611P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2985 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 0.21916(9) 0.30620(7) 0.64770(8) 0.0519(3) Uani 1 1 d . . . O2 O 0.10568(10) 0.63878(7) 0.43200(10) 0.0592(3) Uani 1 1 d . . . O3 O 0.39042(12) 0.06791(9) 0.79918(10) 0.0800(4) Uani 1 1 d . . . H3A H 0.3526 0.1093 0.7408 0.096 Uiso 0.50 1 calc PR . . N1 N 0.27799(10) 0.14580(8) 0.53707(10) 0.0456(3) Uani 1 1 d . . . H1A H 0.2951 0.1481 0.6326 0.055 Uiso 0.50 1 calc PR . . N2 N 0.22350(11) 0.22164(8) 0.44772(11) 0.0473(3) Uani 1 1 d . . . H2A H 0.2071 0.2192 0.3523 0.057 Uiso 1 1 calc R . . C1 C 0.40545(15) -0.00855(11) 0.72077(15) 0.0548(4) Uani 1 1 d . . . C2 C 0.46668(16) -0.08748(13) 0.79994(18) 0.0719(5) Uani 1 1 d . . . H2B H 0.4958 -0.0869 0.9043 0.086 Uiso 1 1 calc R . . C3 C 0.48415(16) -0.16615(13) 0.7246(2) 0.0721(5) Uani 1 1 d . . . H3B H 0.5247 -0.2186 0.7788 0.087 Uiso 1 1 calc R . . C4 C 0.44331(15) -0.16901(12) 0.5715(2) 0.0669(5) Uani 1 1 d . . . H4A H 0.4553 -0.2230 0.5218 0.080 Uiso 1 1 calc R . . C5 C 0.38403(14) -0.09067(11) 0.49171(16) 0.0565(4) Uani 1 1 d . . . H5A H 0.3572 -0.0921 0.3875 0.068 Uiso 1 1 calc R . . C6 C 0.36334(12) -0.00954(10) 0.56336(14) 0.0450(4) Uani 1 1 d . . . C7 C 0.30245(13) 0.07219(10) 0.47495(13) 0.0458(4) Uani 1 1 d . . . H7A H 0.2810 0.0705 0.3712 0.055 Uiso 1 1 calc R . . C8 C 0.19614(12) 0.30007(9) 0.51217(12) 0.0406(3) Uani 1 1 d . . . C9 C 0.13645(12) 0.37932(9) 0.40849(13) 0.0406(3) Uani 1 1 d . . . C10 C 0.15266(13) 0.47023(10) 0.46947(13) 0.0446(4) Uani 1 1 d . . . H10A H 0.2016 0.4793 0.5692 0.054 Uiso 1 1 calc R . . C11 C 0.09627(14) 0.54728(10) 0.38253(14) 0.0466(4) Uani 1 1 d . . . C12 C 0.02215(14) 0.53245(11) 0.23460(14) 0.0528(4) Uani 1 1 d . . . H12A H -0.0170 0.5837 0.1757 0.063 Uiso 1 1 calc R . . C13 C 0.00624(14) 0.44293(11) 0.17458(14) 0.0538(4) Uani 1 1 d . . . H13A H -0.0436 0.4341 0.0752 0.065 Uiso 1 1 calc R . . C14 C 0.06333(13) 0.36526(11) 0.25981(13) 0.0472(4) Uani 1 1 d . . . H14A H 0.0528 0.3047 0.2181 0.057 Uiso 1 1 calc R . . C15 C 0.17890(14) 0.65671(11) 0.58459(14) 0.0550(4) Uani 1 1 d . . . H15A H 0.2647 0.6443 0.6004 0.066 Uiso 1 1 calc R . . H15C H 0.1535 0.6158 0.6508 0.066 Uiso 1 1 calc R . . C16 C 0.16123(17) 0.75878(12) 0.61637(18) 0.0678(5) Uani 1 1 d . . . H16D H 0.2061 0.7723 0.7199 0.102 Uiso 1 1 calc R . . H16A H 0.0755 0.7709 0.5956 0.102 Uiso 1 1 calc R . . H16B H 0.1907 0.7986 0.5540 0.102 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0728(8) 0.0528(7) 0.0282(4) 0.0027(4) 0.0151(4) 0.0014(5) O2 0.0818(8) 0.0413(6) 0.0486(5) 0.0041(4) 0.0148(5) 0.0037(5) O3 0.1191(11) 0.0721(8) 0.0381(5) 0.0004(5) 0.0135(6) 0.0263(7) N1 0.0579(8) 0.0450(7) 0.0318(5) 0.0067(5) 0.0130(5) 0.0044(6) N2 0.0681(9) 0.0436(7) 0.0274(5) 0.0058(5) 0.0126(5) 0.0083(6) C1 0.0611(11) 0.0523(10) 0.0460(7) 0.0045(7) 0.0121(7) 0.0067(8) C2 0.0807(14) 0.0683(12) 0.0548(9) 0.0169(9) 0.0080(9) 0.0148(10) C3 0.0626(12) 0.0646(12) 0.0844(12) 0.0242(10) 0.0192(10) 0.0183(9) C4 0.0672(12) 0.0504(11) 0.0884(12) 0.0011(9) 0.0334(10) 0.0094(9) C5 0.0626(11) 0.0527(10) 0.0556(8) -0.0013(7) 0.0223(8) 0.0016(8) C6 0.0460(9) 0.0442(9) 0.0436(7) 0.0024(6) 0.0139(6) -0.0008(7) C7 0.0547(10) 0.0475(9) 0.0332(6) 0.0000(6) 0.0124(6) -0.0019(7) C8 0.0481(9) 0.0425(8) 0.0308(6) 0.0014(6) 0.0132(6) -0.0033(6) C9 0.0471(9) 0.0433(8) 0.0329(6) 0.0026(6) 0.0159(6) -0.0005(7) C10 0.0528(9) 0.0474(9) 0.0325(6) 0.0028(6) 0.0132(6) 0.0013(7) C11 0.0586(10) 0.0405(9) 0.0431(7) 0.0034(6) 0.0207(7) -0.0016(7) C12 0.0637(11) 0.0485(10) 0.0430(7) 0.0140(7) 0.0141(7) 0.0044(8) C13 0.0653(11) 0.0550(10) 0.0343(6) 0.0061(6) 0.0086(7) -0.0019(8) C14 0.0600(10) 0.0450(9) 0.0347(6) 0.0016(6) 0.0138(6) -0.0009(7) C15 0.0659(11) 0.0483(10) 0.0501(8) -0.0019(7) 0.0188(7) 0.0000(8) C16 0.0791(13) 0.0518(11) 0.0742(10) -0.0084(8) 0.0287(9) -0.0022(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.2240(14) . ? O2 C11 1.3618(16) . ? O2 C15 1.4272(15) . ? O3 C1 1.3532(18) . ? O3 H3A 0.8200 . ? N1 C7 1.2713(16) . ? N1 N2 1.3743(14) . ? N1 H1A 0.8600 . ? N2 C8 1.3515(16) . ? N2 H2A 0.8600 . ? C1 C2 1.391(2) . ? C1 C6 1.4035(18) . ? C2 C3 1.371(2) . ? C2 H2B 0.9300 . ? C3 C4 1.365(2) . ? C3 H3B 0.9300 . ? C4 C5 1.380(2) . ? C4 H4A 0.9300 . ? C5 C6 1.3914(19) . ? C5 H5A 0.9300 . ? C6 C7 1.4553(18) . ? C7 H7A 0.9300 . ? C8 C9 1.4910(18) . ? C9 C14 1.3882(17) . ? C9 C10 1.3898(18) . ? C10 C11 1.3831(18) . ? C10 H10A 0.9300 . ? C11 C12 1.3871(19) . ? C12 C13 1.3686(19) . ? C12 H12A 0.9300 . ? C13 C14 1.3851(19) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.496(2) . ? C15 H15A 0.9700 . ? C15 H15C 0.9700 . ? C16 H16D 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? 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 C11 O2 C15 117.79(11) . . ? C1 O3 H3A 109.5 . . ? C7 N1 N2 118.35(10) . . ? C7 N1 H1A 120.8 . . ? N2 N1 H1A 120.8 . . ? C8 N2 N1 118.96(10) . . ? C8 N2 H2A 120.5 . . ? N1 N2 H2A 120.5 . . ? O3 C1 C2 118.41(13) . . ? O3 C1 C6 122.02(13) . . ? C2 C1 C6 119.55(14) . . ? C3 C2 C1 120.15(15) . . ? C3 C2 H2B 119.9 . . ? C1 C2 H2B 119.9 . . ? C4 C3 C2 121.35(16) . . ? C4 C3 H3B 119.3 . . ? C2 C3 H3B 119.3 . . ? C3 C4 C5 119.07(16) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C4 C5 C6 121.60(14) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C5 C6 C1 118.26(13) . . ? C5 C6 C7 119.83(12) . . ? C1 C6 C7 121.89(13) . . ? N1 C7 C6 121.18(11) . . ? N1 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? O1 C8 N2 122.24(12) . . ? O1 C8 C9 121.67(12) . . ? N2 C8 C9 116.09(10) . . ? C14 C9 C10 120.17(12) . . ? C14 C9 C8 123.17(12) . . ? C10 C9 C8 116.60(11) . . ? C11 C10 C9 120.29(12) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? O2 C11 C10 124.74(12) . . ? O2 C11 C12 116.08(12) . . ? C10 C11 C12 119.16(13) . . ? C13 C12 C11 120.52(13) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C12 C13 C14 120.93(13) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C13 C14 C9 118.91(13) . . ? C13 C14 H14A 120.5 . . ? C9 C14 H14A 120.5 . . ? O2 C15 C16 107.42(12) . . ? O2 C15 H15A 110.2 . . ? C16 C15 H15A 110.2 . . ? O2 C15 H15C 110.2 . . ? C16 C15 H15C 110.2 . . ? H15A C15 H15C 108.5 . . ? C15 C16 H16D 109.5 . . ? C15 C16 H16A 109.5 . . ? H16D C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16D C16 H16B 109.5 . . ? H16A C16 H16B 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 C7 N1 N2 C8 179.49(12) . . . . ? O3 C1 C2 C3 -179.74(16) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C4 C5 C6 C1 0.5(2) . . . . ? C4 C5 C6 C7 178.87(14) . . . . ? O3 C1 C6 C5 179.18(14) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? O3 C1 C6 C7 0.9(2) . . . . ? C2 C1 C6 C7 -177.89(15) . . . . ? N2 N1 C7 C6 178.19(12) . . . . ? C5 C6 C7 N1 177.18(14) . . . . ? C1 C6 C7 N1 -4.5(2) . . . . ? N1 N2 C8 O1 0.6(2) . . . . ? N1 N2 C8 C9 -179.62(11) . . . . ? O1 C8 C9 C14 -151.79(14) . . . . ? N2 C8 C9 C14 28.45(19) . . . . ? O1 C8 C9 C10 25.41(19) . . . . ? N2 C8 C9 C10 -154.36(12) . . . . ? C14 C9 C10 C11 -0.1(2) . . . . ? C8 C9 C10 C11 -177.38(12) . . . . ? C15 O2 C11 C10 0.0(2) . . . . ? C15 O2 C11 C12 178.62(13) . . . . ? C9 C10 C11 O2 179.50(13) . . . . ? C9 C10 C11 C12 0.9(2) . . . . ? O2 C11 C12 C13 -179.64(13) . . . . ? C10 C11 C12 C13 -0.9(2) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C9 0.7(2) . . . . ? C10 C9 C14 C13 -0.7(2) . . . . ? C8 C9 C14 C13 176.42(13) . . . . ? C11 O2 C15 C16 -172.67(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A N1 0.82 1.90 2.6193(13) 146.3 . N1 H1A O3 0.86 1.95 2.6193(13) 134.1 . N2 H2A O1 0.86 2.03 2.8586(12) 162.4 4_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.188 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.035 #===END data_dp241 _database_code_depnum_ccdc_archive 'CCDC 643173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[BSBH(m-OEt)]2 - H2O' _chemical_melting_point ? _chemical_formula_moiety '2(C22 H27 B N2 O4), 0.5(H4 O2)' _chemical_formula_sum 'C44 H56 B2 N4 O9' _chemical_formula_weight 806.55 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 18.293(7) _cell_length_b 8.639(3) _cell_length_c 29.494(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.504(5) _cell_angle_gamma 90.00 _cell_volume 4583(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1902 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 21.78 _exptl_crystal_description Needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8368 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.38 _reflns_number_total 8368 _reflns_number_gt 4048 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex II 2.0 Rev.2 (Bruker, 2005)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT 7.12A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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. There are two unique EtO-BSBH in the asymmetric unit along with a highly disordered water molecule site. One of the two EtO-BSBH [B2] contains a disordered pinacolboronate group that arise from the inversion of the 5- membered ring at the oxygen site [O8 and O8A]. These two conformations led to 2 orientations of the terminal methyl groups [C43A, C44A and C43B, C44B] which were refined to be [60:40]. The water molecule disorder was constrained by AFIX 3, because the positions of the oxygens were highly disordered. All the thermal parameters were constrained in order for the refinement to converge. ; _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^)+(0.1338P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8368 _refine_ls_number_parameters 534 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1576 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.2631 _refine_ls_wR_factor_gt 0.2349 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.080 _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 B1 B 0.3080(3) 0.7984(5) 0.16210(16) 0.0481(11) Uani 1 1 d . . . O1 O 0.59735(15) 0.4031(3) 0.30715(8) 0.0529(7) Uani 1 1 d . . . O2 O 0.75489(16) 0.5251(4) 0.45867(9) 0.0695(9) Uani 1 1 d . . . O3 O 0.31807(17) 0.8626(3) 0.20399(10) 0.0681(9) Uani 1 1 d . . . O4 O 0.25629(19) 0.8724(4) 0.13112(11) 0.0837(11) Uani 1 1 d . . . N1 N 0.48885(17) 0.5453(4) 0.24851(10) 0.0455(8) Uani 1 1 d . . . N2 N 0.51684(17) 0.6041(4) 0.29148(10) 0.0459(8) Uani 1 1 d . . . H2A H 0.5002 0.6898 0.3004 0.055 Uiso 1 1 calc R . . C1 C 0.3502(2) 0.6544(4) 0.14784(13) 0.0444(9) Uani 1 1 d . . . C2 C 0.3275(2) 0.5990(5) 0.10298(14) 0.0601(12) Uani 1 1 d . . . H2B H 0.2878 0.6468 0.0839 0.072 Uiso 1 1 calc R . . C3 C 0.3622(3) 0.4753(6) 0.08625(15) 0.0699(13) Uani 1 1 d . . . H3A H 0.3466 0.4432 0.0559 0.084 Uiso 1 1 calc R . . C4 C 0.4196(3) 0.3990(6) 0.11402(15) 0.0673(13) Uani 1 1 d . . . H4B H 0.4419 0.3134 0.1031 0.081 Uiso 1 1 calc R . . C5 C 0.4435(2) 0.4514(5) 0.15817(14) 0.0521(10) Uani 1 1 d . . . H5A H 0.4831 0.4015 0.1767 0.062 Uiso 1 1 calc R . . C6 C 0.4103(2) 0.5771(4) 0.17612(12) 0.0408(9) Uani 1 1 d . . . C7 C 0.4404(2) 0.6289(4) 0.22332(12) 0.0424(9) Uani 1 1 d . . . H7 H 0.4242 0.7210 0.2345 0.051 Uiso 1 1 calc R . . C8 C 0.5711(2) 0.5247(4) 0.31952(12) 0.0434(9) Uani 1 1 d . . . C9 C 0.5969(2) 0.5885(4) 0.36673(12) 0.0424(9) Uani 1 1 d . . . C10 C 0.6635(2) 0.5353(5) 0.39163(13) 0.0483(10) Uani 1 1 d . . . H10 H 0.6915 0.4642 0.3784 0.058 Uiso 1 1 calc R . . C11 C 0.6887(2) 0.5875(5) 0.43639(13) 0.0505(10) Uani 1 1 d . . . C12 C 0.6479(3) 0.6943(5) 0.45565(14) 0.0571(11) Uani 1 1 d . . . H12 H 0.6650 0.7312 0.4853 0.068 Uiso 1 1 calc R . . C13 C 0.5816(3) 0.7464(5) 0.43079(14) 0.0637(13) Uani 1 1 d . . . H13 H 0.5539 0.8183 0.4440 0.076 Uiso 1 1 calc R . . C14 C 0.5555(2) 0.6945(5) 0.38698(13) 0.0524(11) Uani 1 1 d . . . H14 H 0.5101 0.7300 0.3708 0.063 Uiso 1 1 calc R . . C15 C 0.7797(3) 0.5686(7) 0.50562(15) 0.0825(16) Uani 1 1 d . . . H15A H 0.7418 0.5454 0.5238 0.099 Uiso 1 1 calc R . . H15B H 0.7903 0.6786 0.5079 0.099 Uiso 1 1 calc R . . C16 C 0.8485(3) 0.4772(9) 0.52261(19) 0.112(2) Uani 1 1 d . . . H16A H 0.8405 0.3711 0.5133 0.168 Uiso 1 1 calc R . . H16B H 0.8603 0.4828 0.5556 0.168 Uiso 1 1 calc R . . H16C H 0.8889 0.5187 0.5098 0.168 Uiso 1 1 calc R . . C17 C 0.2767(3) 1.0076(5) 0.20069(17) 0.0646(12) Uani 1 1 d . . . C18 C 0.2193(3) 0.9847(6) 0.15726(18) 0.0718(14) Uani 1 1 d . . . C19 C 0.2494(3) 1.0337(7) 0.24504(19) 0.0989(19) Uani 1 1 d . . . H19A H 0.2177 0.9496 0.2503 0.148 Uiso 1 1 calc R . . H19B H 0.2220 1.1290 0.2432 0.148 Uiso 1 1 calc R . . H19C H 0.2911 1.0393 0.2700 0.148 Uiso 1 1 calc R . . C20 C 0.3327(3) 1.1350(7) 0.1951(3) 0.130(3) Uani 1 1 d . . . H20A H 0.3755 1.1260 0.2192 0.195 Uiso 1 1 calc R . . H20B H 0.3101 1.2345 0.1969 0.195 Uiso 1 1 calc R . . H20C H 0.3476 1.1243 0.1657 0.195 Uiso 1 1 calc R . . C21 C 0.1494(3) 0.9028(8) 0.1683(3) 0.124(3) Uani 1 1 d . . . H21A H 0.1182 0.8708 0.1401 0.187 Uiso 1 1 calc R . . H21B H 0.1224 0.9731 0.1844 0.187 Uiso 1 1 calc R . . H21C H 0.1641 0.8139 0.1872 0.187 Uiso 1 1 calc R . . C22 C 0.1981(5) 1.1221(8) 0.1274(2) 0.141(3) Uani 1 1 d . . . H22A H 0.2418 1.1657 0.1186 0.211 Uiso 1 1 calc R . . H22B H 0.1752 1.1980 0.1441 0.211 Uiso 1 1 calc R . . H22C H 0.1638 1.0915 0.1003 0.211 Uiso 1 1 calc R . . B2 B 0.6449(3) 0.2965(6) 0.16013(17) 0.0512(12) Uani 1 1 d . . . O5 O 0.44999(17) -0.0994(3) 0.31064(9) 0.0562(8) Uani 1 1 d . . . O6 O 0.3818(2) 0.0620(4) 0.46455(10) 0.0757(10) Uani 1 1 d . . . O7 O 0.65939(19) 0.3629(4) 0.20120(11) 0.0764(10) Uani 1 1 d . A . O8 O 0.6665(4) 0.3881(7) 0.1253(2) 0.0597(16) Uani 0.60 1 d P A 1 O8B O 0.6910(7) 0.3425(14) 0.1338(4) 0.071(4) Uiso 0.40 1 d P A 2 N3 N 0.51783(17) 0.0450(4) 0.24835(10) 0.0453(8) Uani 1 1 d . . . N4 N 0.51619(18) 0.1062(4) 0.29161(10) 0.0486(8) Uani 1 1 d . . . H4A H 0.5370 0.1938 0.2996 0.058 Uiso 1 1 calc R . . C23 C 0.5964(2) 0.1481(5) 0.14711(13) 0.0477(10) Uani 1 1 d . A . C24 C 0.5958(3) 0.0838(6) 0.10370(14) 0.0669(13) Uani 1 1 d . . . H24A H 0.6256 0.1285 0.0848 0.080 Uiso 1 1 calc R A . C25 C 0.5533(3) -0.0429(6) 0.08742(16) 0.0764(15) Uani 1 1 d . A . H25A H 0.5538 -0.0811 0.0580 0.092 Uiso 1 1 calc R . . C26 C 0.5103(3) -0.1118(5) 0.11528(15) 0.0625(12) Uani 1 1 d . . . H26A H 0.4817 -0.1981 0.1048 0.075 Uiso 1 1 calc R A . C27 C 0.5092(2) -0.0541(5) 0.15848(13) 0.0519(10) Uani 1 1 d . A . H27A H 0.4792 -0.1008 0.1768 0.062 Uiso 1 1 calc R . . C28 C 0.5522(2) 0.0731(4) 0.17541(12) 0.0407(9) Uani 1 1 d . . . C29 C 0.5498(2) 0.1294(5) 0.22219(12) 0.0439(9) Uani 1 1 d . A . H29 H 0.5709 0.2239 0.2324 0.053 Uiso 1 1 calc R . . C30 C 0.4814(2) 0.0265(5) 0.32113(12) 0.0445(9) Uani 1 1 d . . . C31 C 0.4822(2) 0.0994(4) 0.36713(13) 0.0465(10) Uani 1 1 d . . . C32 C 0.4317(2) 0.0428(5) 0.39342(13) 0.0509(10) Uani 1 1 d . . . H32 H 0.4001 -0.0386 0.3824 0.061 Uiso 1 1 calc R . . C33 C 0.4288(2) 0.1085(5) 0.43599(14) 0.0557(11) Uani 1 1 d . . . C34 C 0.4759(3) 0.2283(5) 0.45229(14) 0.0612(12) Uani 1 1 d . . . H34 H 0.4730 0.2739 0.4805 0.073 Uiso 1 1 calc R . . C35 C 0.5272(3) 0.2810(5) 0.42713(14) 0.0625(12) Uani 1 1 d . . . H35 H 0.5591 0.3614 0.4385 0.075 Uiso 1 1 calc R . . C36 C 0.5316(2) 0.2149(5) 0.38485(13) 0.0514(10) Uani 1 1 d . . . H36 H 0.5676 0.2481 0.3685 0.062 Uiso 1 1 calc R . . C37 C 0.3489(3) -0.0834(6) 0.45850(16) 0.0700(13) Uani 1 1 d . . . H37A H 0.3863 -0.1618 0.4569 0.084 Uiso 1 1 calc R . . H37B H 0.3128 -0.0861 0.4300 0.084 Uiso 1 1 calc R . . C38 C 0.3112(3) -0.1137(7) 0.49898(18) 0.0859(16) Uani 1 1 d . . . H38A H 0.3476 -0.1129 0.5269 0.129 Uiso 1 1 calc R . . H38B H 0.2873 -0.2129 0.4954 0.129 Uiso 1 1 calc R . . H38C H 0.2749 -0.0347 0.5005 0.129 Uiso 1 1 calc R . . C39 C 0.6980(3) 0.5085(5) 0.19742(17) 0.0644(12) Uani 1 1 d . . . C40 C 0.7240(3) 0.4902(6) 0.1522(2) 0.0832(16) Uani 1 1 d D A . C41 C 0.6402(3) 0.6363(7) 0.1962(2) 0.109(2) Uani 1 1 d . A . H41A H 0.6056 0.6317 0.1675 0.164 Uiso 1 1 calc R . . H41B H 0.6646 0.7352 0.1990 0.164 Uiso 1 1 calc R . . H41C H 0.6141 0.6226 0.2213 0.164 Uiso 1 1 calc R . . C42 C 0.7551(4) 0.5299(8) 0.2401(2) 0.119(2) Uani 1 1 d . A . H42A H 0.7318 0.5243 0.2666 0.179 Uiso 1 1 calc R . . H42B H 0.7784 0.6292 0.2392 0.179 Uiso 1 1 calc R . . H42C H 0.7920 0.4500 0.2418 0.179 Uiso 1 1 calc R . . C43A C 0.7407(7) 0.6273(15) 0.1275(5) 0.126(5) Uiso 0.60 1 d P A 1 H43A H 0.6953 0.6815 0.1157 0.189 Uiso 0.60 1 calc PR A 1 H43B H 0.7643 0.5973 0.1023 0.189 Uiso 0.60 1 calc PR A 1 H43C H 0.7733 0.6938 0.1480 0.189 Uiso 0.60 1 calc PR A 1 C43B C 0.7010(10) 0.6255(15) 0.1177(5) 0.100 Uiso 0.40 1 d PD A 2 H43D H 0.6485 0.6437 0.1145 0.150 Uiso 0.40 1 calc PR A 2 H43E H 0.7126 0.5988 0.0882 0.150 Uiso 0.40 1 calc PR A 2 H43F H 0.7276 0.7175 0.1291 0.150 Uiso 0.40 1 calc PR A 2 C44A C 0.8018(4) 0.4094(11) 0.1673(3) 0.094(3) Uiso 0.60 1 d PD A 1 H44A H 0.8239 0.3912 0.1407 0.141 Uiso 0.60 1 calc PR A 1 H44B H 0.7952 0.3126 0.1820 0.141 Uiso 0.60 1 calc PR A 1 H44C H 0.8337 0.4752 0.1885 0.141 Uiso 0.60 1 calc PR A 1 C44B C 0.7995(3) 0.4606(9) 0.1405(2) 0.100 Uiso 0.40 1 d PD A 2 H44D H 0.8016 0.5045 0.1109 0.150 Uiso 0.40 1 calc PR A 2 H44E H 0.8080 0.3511 0.1398 0.150 Uiso 0.40 1 calc PR A 2 H44F H 0.8369 0.5075 0.1635 0.150 Uiso 0.40 1 calc PR A 2 O1W O 0.6276(3) 0.4252(9) 0.0282(2) 0.120 Uiso 0.373(3) 1 d PR B 1 H1WA H 0.6708 0.3661 0.0272 0.144 Uiso 0.373(3) 1 d PR B 1 H1WB H 0.5822 0.3758 0.0125 0.144 Uiso 0.373(3) 1 d PR B 1 O2W O 0.5174(3) 0.3966(9) 0.0034(2) 0.120 Uiso 0.328(6) 1 d PR C 2 H2WA H 0.5056 0.4981 -0.0003 0.144 Uiso 0.328(6) 1 d PR C 2 H2WB H 0.5668 0.3728 0.0208 0.144 Uiso 0.328(6) 1 d PR C 2 O3W O 0.5488(3) 0.5199(9) 0.0247(2) 0.120 Uiso 0.299(6) 1 d PR D 3 H3WA H 0.5858 0.5853 0.0373 0.144 Uiso 0.299(6) 1 d PR D 3 H3WB H 0.5456 0.5101 -0.0083 0.144 Uiso 0.299(6) 1 d PR D 3 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 B1 0.046(3) 0.046(3) 0.052(3) -0.002(2) 0.007(2) -0.003(2) O1 0.0643(19) 0.0494(17) 0.0428(15) -0.0119(13) 0.0035(13) 0.0078(15) O2 0.0599(19) 0.095(2) 0.0484(17) -0.0157(16) -0.0029(14) 0.0065(18) O3 0.072(2) 0.0605(19) 0.068(2) -0.0054(15) 0.0026(16) 0.0272(17) O4 0.086(2) 0.087(2) 0.071(2) 0.0003(18) -0.0042(18) 0.041(2) N1 0.0485(19) 0.0455(19) 0.0411(17) -0.0064(15) 0.0042(15) 0.0050(17) N2 0.056(2) 0.0422(18) 0.0367(17) -0.0122(14) 0.0005(15) 0.0041(16) C1 0.042(2) 0.045(2) 0.046(2) 0.0003(18) 0.0071(18) -0.0026(19) C2 0.058(3) 0.068(3) 0.049(3) -0.004(2) -0.005(2) 0.008(2) C3 0.071(3) 0.084(3) 0.051(3) -0.024(2) 0.000(2) 0.001(3) C4 0.070(3) 0.070(3) 0.061(3) -0.025(2) 0.007(2) 0.010(3) C5 0.044(2) 0.057(3) 0.052(2) -0.006(2) 0.0011(19) 0.004(2) C6 0.042(2) 0.044(2) 0.038(2) -0.0011(17) 0.0109(17) 0.0002(18) C7 0.042(2) 0.042(2) 0.046(2) -0.0028(18) 0.0136(18) 0.0022(19) C8 0.050(2) 0.039(2) 0.042(2) -0.0014(18) 0.0109(19) -0.002(2) C9 0.054(2) 0.037(2) 0.036(2) -0.0018(16) 0.0079(18) 0.0003(19) C10 0.053(3) 0.047(2) 0.047(2) -0.0081(18) 0.0138(19) -0.001(2) C11 0.056(3) 0.055(3) 0.038(2) -0.0050(19) 0.0033(19) -0.001(2) C12 0.068(3) 0.065(3) 0.037(2) -0.011(2) 0.007(2) 0.001(2) C13 0.082(3) 0.067(3) 0.045(2) -0.012(2) 0.019(2) 0.014(3) C14 0.055(3) 0.059(3) 0.044(2) -0.002(2) 0.0112(19) 0.008(2) C15 0.078(4) 0.114(4) 0.050(3) -0.015(3) -0.003(2) -0.011(3) C16 0.082(4) 0.165(7) 0.078(4) -0.001(4) -0.015(3) 0.016(4) C17 0.058(3) 0.049(3) 0.088(3) -0.003(2) 0.018(3) 0.016(2) C18 0.061(3) 0.060(3) 0.091(4) -0.007(3) 0.006(3) 0.024(3) C19 0.111(5) 0.086(4) 0.104(4) -0.020(3) 0.030(4) 0.033(4) C20 0.078(4) 0.069(4) 0.252(9) -0.034(5) 0.054(5) -0.017(3) C21 0.054(3) 0.117(5) 0.199(8) -0.035(5) 0.015(4) 0.000(4) C22 0.180(7) 0.107(5) 0.133(6) 0.049(4) 0.026(5) 0.084(5) B2 0.045(3) 0.061(3) 0.052(3) 0.003(2) 0.021(2) -0.003(2) O5 0.077(2) 0.0453(17) 0.0497(17) -0.0064(13) 0.0201(14) -0.0017(16) O6 0.108(3) 0.068(2) 0.064(2) -0.0193(16) 0.0488(19) -0.029(2) O7 0.100(3) 0.060(2) 0.074(2) -0.0139(16) 0.0296(19) -0.0327(19) O8 0.069(4) 0.052(4) 0.060(4) 0.011(3) 0.018(3) -0.015(4) N3 0.052(2) 0.0482(19) 0.0371(17) -0.0077(15) 0.0111(15) -0.0023(16) N4 0.061(2) 0.0447(19) 0.0435(18) -0.0110(15) 0.0172(16) -0.0065(17) C23 0.045(2) 0.055(2) 0.045(2) -0.0036(19) 0.0147(18) -0.005(2) C24 0.072(3) 0.081(3) 0.054(3) -0.013(2) 0.029(2) -0.015(3) C25 0.092(4) 0.085(4) 0.059(3) -0.025(3) 0.033(3) -0.017(3) C26 0.073(3) 0.060(3) 0.057(3) -0.017(2) 0.016(2) -0.017(2) C27 0.053(2) 0.056(3) 0.049(2) -0.006(2) 0.0153(19) -0.009(2) C28 0.041(2) 0.043(2) 0.040(2) -0.0041(17) 0.0097(17) 0.0000(18) C29 0.040(2) 0.048(2) 0.042(2) -0.0027(18) 0.0050(17) -0.0054(19) C30 0.048(2) 0.044(2) 0.041(2) 0.0021(18) 0.0081(18) 0.009(2) C31 0.054(2) 0.044(2) 0.044(2) -0.0004(18) 0.0139(19) 0.005(2) C32 0.058(3) 0.046(2) 0.052(2) -0.0067(19) 0.018(2) -0.007(2) C33 0.068(3) 0.052(3) 0.052(3) -0.009(2) 0.022(2) -0.002(2) C34 0.082(3) 0.062(3) 0.042(2) -0.010(2) 0.017(2) -0.011(3) C35 0.072(3) 0.065(3) 0.049(3) -0.014(2) 0.008(2) -0.016(2) C36 0.055(3) 0.057(3) 0.042(2) -0.0032(19) 0.0102(19) -0.007(2) C37 0.075(3) 0.066(3) 0.073(3) -0.003(2) 0.026(3) -0.011(3) C38 0.080(4) 0.096(4) 0.084(4) 0.006(3) 0.023(3) -0.018(3) C39 0.059(3) 0.049(3) 0.088(3) -0.007(2) 0.019(3) -0.018(2) C40 0.085(4) 0.059(3) 0.117(4) -0.004(3) 0.047(3) -0.024(3) C41 0.095(4) 0.071(4) 0.170(6) -0.017(4) 0.047(4) 0.011(3) C42 0.113(5) 0.116(5) 0.115(5) -0.009(4) -0.018(4) -0.031(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 B1 O3 1.336(5) . ? B1 O4 1.350(5) . ? B1 C1 1.562(6) . ? O1 C8 1.237(4) . ? O2 C11 1.378(5) . ? O2 C15 1.427(5) . ? O3 C17 1.458(5) . ? O4 C18 1.478(5) . ? N1 C7 1.273(5) . ? N1 N2 1.375(4) . ? N2 C8 1.357(5) . ? N2 H2A 0.8600 . ? C1 C2 1.397(5) . ? C1 C6 1.420(5) . ? C2 C3 1.379(6) . ? C2 H2B 0.9300 . ? C3 C4 1.377(6) . ? C3 H3A 0.9300 . ? C4 C5 1.373(5) . ? C4 H4B 0.9300 . ? C5 C6 1.394(5) . ? C5 H5A 0.9300 . ? C6 C7 1.470(5) . ? C7 H7 0.9300 . ? C8 C9 1.492(5) . ? C9 C10 1.381(5) . ? C9 C14 1.391(5) . ? C10 C11 1.392(5) . ? C10 H10 0.9300 . ? C11 C12 1.373(6) . ? C12 C13 1.373(6) . ? C12 H12 0.9300 . ? C13 C14 1.369(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.493(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C19 1.500(7) . ? C17 C18 1.514(7) . ? C17 C20 1.533(7) . ? C18 C22 1.487(7) . ? C18 C21 1.548(8) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? B2 O8B 1.308(13) . ? B2 O7 1.323(5) . ? B2 O8 1.408(7) . ? B2 C23 1.567(6) . ? O5 C30 1.243(5) . ? O6 C33 1.368(5) . ? O6 C37 1.390(5) . ? O7 C39 1.456(5) . ? O8 C40 1.486(8) . ? O8B C40 1.473(13) . ? N3 C29 1.278(5) . ? N3 N4 1.386(4) . ? N4 C30 1.356(5) . ? N4 H4A 0.8600 . ? C23 C24 1.394(5) . ? C23 C28 1.420(5) . ? C24 C25 1.377(6) . ? C24 H24A 0.9300 . ? C25 C26 1.373(6) . ? C25 H25A 0.9300 . ? C26 C27 1.372(5) . ? C26 H26A 0.9300 . ? C27 C28 1.390(5) . ? C27 H27A 0.9300 . ? C28 C29 1.471(5) . ? C29 H29 0.9300 . ? C30 C31 1.493(5) . ? C31 C36 1.383(5) . ? C31 C32 1.399(5) . ? C32 C33 1.388(5) . ? C32 H32 0.9300 . ? C33 C34 1.376(6) . ? C34 C35 1.376(6) . ? C34 H34 0.9300 . ? C35 C36 1.387(5) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.506(6) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 C42 1.494(7) . ? C39 C40 1.504(7) . ? C39 C41 1.524(7) . ? C40 C43A 1.452(13) . ? C40 C44B 1.504(4) . ? C40 C43B 1.556(5) . ? C40 C44A 1.575(5) . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43A H43A 0.9600 . ? C43A H43B 0.9600 . ? C43A H43C 0.9600 . ? C43B H43D 0.9600 . ? C43B H43E 0.9600 . ? C43B H43F 0.9600 . ? C44A H44A 0.9600 . ? C44A H44B 0.9600 . ? C44A H44C 0.9600 . ? C44B H44D 0.9600 . ? C44B H44E 0.9600 . ? C44B H44F 0.9600 . ? O1W H1WA 0.9465 . ? O1W H1WB 0.9726 . ? O2W H2WA 0.9046 . ? O2W H2WB 0.9763 . ? O3W H3WA 0.9075 . ? O3W H3WB 0.9653 . ? 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 O3 B1 O4 113.0(4) . . ? O3 B1 C1 126.0(4) . . ? O4 B1 C1 121.0(4) . . ? C11 O2 C15 117.1(4) . . ? B1 O3 C17 108.2(3) . . ? B1 O4 C18 106.8(4) . . ? C7 N1 N2 115.5(3) . . ? C8 N2 N1 118.9(3) . . ? C8 N2 H2A 120.6 . . ? N1 N2 H2A 120.6 . . ? C2 C1 C6 117.4(4) . . ? C2 C1 B1 116.8(4) . . ? C6 C1 B1 125.8(3) . . ? C3 C2 C1 121.8(4) . . ? C3 C2 H2B 119.1 . . ? C1 C2 H2B 119.1 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 H4B 120.6 . . ? C3 C4 H4B 120.6 . . ? C4 C5 C6 122.1(4) . . ? C4 C5 H5A 118.9 . . ? C6 C5 H5A 118.9 . . ? C5 C6 C1 119.2(3) . . ? C5 C6 C7 118.9(3) . . ? C1 C6 C7 121.9(3) . . ? N1 C7 C6 118.7(3) . . ? N1 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? O1 C8 N2 122.0(3) . . ? O1 C8 C9 121.0(3) . . ? N2 C8 C9 117.0(3) . . ? C10 C9 C14 119.2(3) . . ? C10 C9 C8 118.1(3) . . ? C14 C9 C8 122.7(4) . . ? C9 C10 C11 120.3(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 O2 124.2(4) . . ? C12 C11 C10 119.9(4) . . ? O2 C11 C10 115.8(4) . . ? C11 C12 C13 119.5(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 121.3(4) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C9 119.8(4) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? O2 C15 C16 106.6(4) . . ? O2 C15 H15A 110.4 . . ? C16 C15 H15A 110.4 . . ? O2 C15 H15B 110.4 . . ? C16 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C17 C19 108.8(4) . . ? O3 C17 C18 102.4(3) . . ? C19 C17 C18 117.9(4) . . ? O3 C17 C20 106.0(4) . . ? C19 C17 C20 108.7(5) . . ? C18 C17 C20 112.1(5) . . ? O4 C18 C22 108.1(5) . . ? O4 C18 C17 102.4(3) . . ? C22 C18 C17 117.5(5) . . ? O4 C18 C21 106.5(4) . . ? C22 C18 C21 110.7(5) . . ? C17 C18 C21 110.8(5) . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O8B B2 O7 111.7(7) . . ? O7 B2 O8 112.8(5) . . ? O8B B2 C23 120.0(7) . . ? O7 B2 C23 126.1(4) . . ? O8 B2 C23 120.2(4) . . ? C33 O6 C37 119.5(3) . . ? B2 O7 C39 108.9(4) . . ? B2 O8 C40 102.1(5) . . ? B2 O8B C40 108.0(9) . . ? C29 N3 N4 115.3(3) . . ? C30 N4 N3 119.2(3) . . ? C30 N4 H4A 120.4 . . ? N3 N4 H4A 120.4 . . ? C24 C23 C28 116.6(4) . . ? C24 C23 B2 117.4(4) . . ? C28 C23 B2 126.0(3) . . ? C25 C24 C23 123.1(4) . . ? C25 C24 H24A 118.4 . . ? C23 C24 H24A 118.4 . . ? C26 C25 C24 119.0(4) . . ? C26 C25 H25A 120.5 . . ? C24 C25 H25A 120.5 . . ? C27 C26 C25 120.3(4) . . ? C27 C26 H26A 119.9 . . ? C25 C26 H26A 119.9 . . ? C26 C27 C28 121.2(4) . . ? C26 C27 H27A 119.4 . . ? C28 C27 H27A 119.4 . . ? C27 C28 C23 119.7(3) . . ? C27 C28 C29 119.1(3) . . ? C23 C28 C29 121.2(3) . . ? N3 C29 C28 118.2(3) . . ? N3 C29 H29 120.9 . . ? C28 C29 H29 120.9 . . ? O5 C30 N4 122.3(3) . . ? O5 C30 C31 121.5(3) . . ? N4 C30 C31 116.2(4) . . ? C36 C31 C32 119.7(4) . . ? C36 C31 C30 123.1(4) . . ? C32 C31 C30 117.2(4) . . ? C33 C32 C31 119.8(4) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? O6 C33 C34 115.4(4) . . ? O6 C33 C32 124.6(4) . . ? C34 C33 C32 120.0(4) . . ? C33 C34 C35 120.4(4) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 120.4(4) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 119.7(4) . . ? C31 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? O6 C37 C38 107.8(4) . . ? O6 C37 H37A 110.1 . . ? C38 C37 H37A 110.1 . . ? O6 C37 H37B 110.1 . . ? C38 C37 H37B 110.1 . . ? H37A C37 H37B 108.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O7 C39 C42 108.5(4) . . ? O7 C39 C40 102.3(3) . . ? C42 C39 C40 118.3(4) . . ? O7 C39 C41 106.5(4) . . ? C42 C39 C41 107.8(5) . . ? C40 C39 C41 112.7(5) . . ? C43A C40 O8B 129.1(8) . . ? C43A C40 O8 114.1(7) . . ? C43A C40 C39 119.3(7) . . ? O8B C40 C39 104.1(6) . . ? O8 C40 C39 103.2(4) . . ? O8B C40 C44B 95.7(6) . . ? O8 C40 C44B 111.5(5) . . ? C39 C40 C44B 132.3(5) . . ? O8B C40 C43B 111.4(9) . . ? O8 C40 C43B 90.9(8) . . ? C39 C40 C43B 114.1(8) . . ? C44B C40 C43B 97.4(8) . . ? C43A C40 C44A 104.0(7) . . ? O8B C40 C44A 90.5(6) . . ? O8 C40 C44A 113.8(6) . . ? C39 C40 C44A 102.2(5) . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C40 C43A H43A 109.5 . . ? C40 C43A H43B 109.5 . . ? H43A C43A H43B 109.5 . . ? C40 C43A H43C 109.5 . . ? H43A C43A H43C 109.5 . . ? H43B C43A H43C 109.5 . . ? C40 C43B H43D 109.5 . . ? C40 C43B H43E 109.5 . . ? H43D C43B H43E 109.5 . . ? C40 C43B H43F 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? C40 C44A H44A 109.5 . . ? C40 C44A H44B 109.5 . . ? H44A C44A H44B 109.5 . . ? C40 C44A H44C 109.5 . . ? H44A C44A H44C 109.5 . . ? H44B C44A H44C 109.5 . . ? C40 C44B H44D 109.5 . . ? C40 C44B H44E 109.5 . . ? H44D C44B H44E 109.5 . . ? C40 C44B H44F 109.5 . . ? H44D C44B H44F 109.5 . . ? H44E C44B H44F 109.5 . . ? H1WA O1W H1WB 113.3 . . ? H2WA O2W H2WB 116.4 . . ? H3WA O3W H3WB 111.8 . . ? 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 O4 B1 O3 C17 -8.3(5) . . . . ? C1 B1 O3 C17 171.0(4) . . . . ? O3 B1 O4 C18 -9.6(5) . . . . ? C1 B1 O4 C18 171.0(4) . . . . ? C7 N1 N2 C8 -177.1(3) . . . . ? O3 B1 C1 C2 175.5(4) . . . . ? O4 B1 C1 C2 -5.3(6) . . . . ? O3 B1 C1 C6 -5.7(7) . . . . ? O4 B1 C1 C6 173.6(4) . . . . ? C6 C1 C2 C3 -0.8(6) . . . . ? B1 C1 C2 C3 178.1(4) . . . . ? C1 C2 C3 C4 1.9(7) . . . . ? C2 C3 C4 C5 -2.2(7) . . . . ? C3 C4 C5 C6 1.5(7) . . . . ? C4 C5 C6 C1 -0.5(6) . . . . ? C4 C5 C6 C7 -178.4(4) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? B1 C1 C6 C5 -178.7(4) . . . . ? C2 C1 C6 C7 177.9(4) . . . . ? B1 C1 C6 C7 -0.9(6) . . . . ? N2 N1 C7 C6 177.2(3) . . . . ? C5 C6 C7 N1 -9.5(5) . . . . ? C1 C6 C7 N1 172.7(3) . . . . ? N1 N2 C8 O1 1.8(5) . . . . ? N1 N2 C8 C9 -176.8(3) . . . . ? O1 C8 C9 C10 17.6(5) . . . . ? N2 C8 C9 C10 -163.8(3) . . . . ? O1 C8 C9 C14 -160.1(4) . . . . ? N2 C8 C9 C14 18.5(5) . . . . ? C14 C9 C10 C11 -0.2(6) . . . . ? C8 C9 C10 C11 -177.9(3) . . . . ? C15 O2 C11 C12 3.8(6) . . . . ? C15 O2 C11 C10 -175.9(4) . . . . ? C9 C10 C11 C12 -1.1(6) . . . . ? C9 C10 C11 O2 178.7(3) . . . . ? O2 C11 C12 C13 -178.4(4) . . . . ? C10 C11 C12 C13 1.3(6) . . . . ? C11 C12 C13 C14 -0.4(7) . . . . ? C12 C13 C14 C9 -0.8(7) . . . . ? C10 C9 C14 C13 1.1(6) . . . . ? C8 C9 C14 C13 178.7(4) . . . . ? C11 O2 C15 C16 175.7(4) . . . . ? B1 O3 C17 C19 147.3(4) . . . . ? B1 O3 C17 C18 21.8(5) . . . . ? B1 O3 C17 C20 -95.9(5) . . . . ? B1 O4 C18 C22 147.1(5) . . . . ? B1 O4 C18 C17 22.3(5) . . . . ? B1 O4 C18 C21 -94.0(5) . . . . ? O3 C17 C18 O4 -26.0(4) . . . . ? C19 C17 C18 O4 -145.4(4) . . . . ? C20 C17 C18 O4 87.2(5) . . . . ? O3 C17 C18 C22 -144.2(5) . . . . ? C19 C17 C18 C22 96.4(6) . . . . ? C20 C17 C18 C22 -31.0(7) . . . . ? O3 C17 C18 C21 87.2(4) . . . . ? C19 C17 C18 C21 -32.1(6) . . . . ? C20 C17 C18 C21 -159.5(4) . . . . ? O8B B2 O7 C39 24.4(7) . . . . ? O8 B2 O7 C39 -3.5(6) . . . . ? C23 B2 O7 C39 -172.6(4) . . . . ? O8B B2 O8 C40 -70.2(16) . . . . ? O7 B2 O8 C40 22.7(7) . . . . ? C23 B2 O8 C40 -167.5(4) . . . . ? O7 B2 O8B C40 -20.4(9) . . . . ? O8 B2 O8B C40 77.4(15) . . . . ? C23 B2 O8B C40 175.4(5) . . . . ? C29 N3 N4 C30 178.0(3) . . . . ? O8B B2 C23 C24 -9.8(8) . . . . ? O7 B2 C23 C24 -171.6(5) . . . . ? O8 B2 C23 C24 20.1(7) . . . . ? O8B B2 C23 C28 170.7(6) . . . . ? O7 B2 C23 C28 8.9(7) . . . . ? O8 B2 C23 C28 -159.4(5) . . . . ? C28 C23 C24 C25 2.1(7) . . . . ? B2 C23 C24 C25 -177.4(5) . . . . ? C23 C24 C25 C26 -1.3(8) . . . . ? C24 C25 C26 C27 0.7(8) . . . . ? C25 C26 C27 C28 -1.1(7) . . . . ? C26 C27 C28 C23 2.0(6) . . . . ? C26 C27 C28 C29 -179.3(4) . . . . ? C24 C23 C28 C27 -2.4(6) . . . . ? B2 C23 C28 C27 177.1(4) . . . . ? C24 C23 C28 C29 178.8(4) . . . . ? B2 C23 C28 C29 -1.6(6) . . . . ? N4 N3 C29 C28 -178.8(3) . . . . ? C27 C28 C29 N3 11.2(5) . . . . ? C23 C28 C29 N3 -170.1(4) . . . . ? N3 N4 C30 O5 -0.8(6) . . . . ? N3 N4 C30 C31 179.7(3) . . . . ? O5 C30 C31 C36 162.4(4) . . . . ? N4 C30 C31 C36 -18.1(5) . . . . ? O5 C30 C31 C32 -15.6(5) . . . . ? N4 C30 C31 C32 163.8(3) . . . . ? C36 C31 C32 C33 3.4(6) . . . . ? C30 C31 C32 C33 -178.5(4) . . . . ? C37 O6 C33 C34 -160.7(4) . . . . ? C37 O6 C33 C32 18.6(7) . . . . ? C31 C32 C33 O6 -179.7(4) . . . . ? C31 C32 C33 C34 -0.4(6) . . . . ? O6 C33 C34 C35 177.8(4) . . . . ? C32 C33 C34 C35 -1.6(7) . . . . ? C33 C34 C35 C36 0.6(7) . . . . ? C32 C31 C36 C35 -4.4(6) . . . . ? C30 C31 C36 C35 177.6(4) . . . . ? C34 C35 C36 C31 2.5(7) . . . . ? C33 O6 C37 C38 170.6(4) . . . . ? B2 O7 C39 C42 -142.8(5) . . . . ? B2 O7 C39 C40 -17.1(5) . . . . ? B2 O7 C39 C41 101.4(5) . . . . ? B2 O8B C40 C43A -140.3(9) . . . . ? B2 O8B C40 O8 -82.5(16) . . . . ? B2 O8B C40 C39 8.3(8) . . . . ? B2 O8B C40 C44B 144.6(7) . . . . ? B2 O8B C40 C43B -115.2(10) . . . . ? B2 O8B C40 C44A 111.0(8) . . . . ? B2 O8 C40 C43A -162.5(7) . . . . ? B2 O8 C40 O8B 63.5(15) . . . . ? B2 O8 C40 C39 -31.6(6) . . . . ? B2 O8 C40 C44B 115.0(6) . . . . ? B2 O8 C40 C43B -146.6(8) . . . . ? B2 O8 C40 C44A 78.3(7) . . . . ? O7 C39 C40 C43A 157.5(7) . . . . ? C42 C39 C40 C43A -83.4(8) . . . . ? C41 C39 C40 C43A 43.5(8) . . . . ? O7 C39 C40 O8B 5.1(6) . . . . ? C42 C39 C40 O8B 124.2(6) . . . . ? C41 C39 C40 O8B -108.9(6) . . . . ? O7 C39 C40 O8 29.7(5) . . . . ? C42 C39 C40 O8 148.8(5) . . . . ? C41 C39 C40 O8 -84.2(5) . . . . ? O7 C39 C40 C44B -106.5(6) . . . . ? C42 C39 C40 C44B 12.6(8) . . . . ? C41 C39 C40 C44B 139.5(6) . . . . ? O7 C39 C40 C43B 126.8(8) . . . . ? C42 C39 C40 C43B -114.1(9) . . . . ? C41 C39 C40 C43B 12.8(9) . . . . ? O7 C39 C40 C44A -88.6(5) . . . . ? C42 C39 C40 C44A 30.5(7) . . . . ? C41 C39 C40 C44A 157.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O5 0.86 2.09 2.937(4) 170.2 1_565 N4 H4A O1 0.86 2.11 2.957(4) 168.4 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.357 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.054 #===END data_dp224 _database_code_depnum_ccdc_archive 'CCDC 643174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SBH(OMe)3 _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N2 O5' _chemical_formula_sum 'C17 H18 N2 O5' _chemical_formula_weight 330.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _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 14.787(7) _cell_length_b 13.198(6) _cell_length_c 8.225(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.262(5) _cell_angle_gamma 90.00 _cell_volume 1574.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 632 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 22.81 _exptl_crystal_description Needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2811 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2811 _reflns_number_gt 1585 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex II 2.0 Rev.2 (Bruker, 2005)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT 7.12A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0483P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2811 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1105 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _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 0.73148(13) 0.35355(13) 0.7380(2) 0.0297(5) Uani 1 1 d . . . O2 O 0.81476(13) 0.63709(13) 0.3529(2) 0.0381(5) Uani 1 1 d . . . O3 O 0.92941(13) 0.54502(13) 0.1882(2) 0.0343(5) Uani 1 1 d . . . O4 O 0.96986(13) 0.35086(13) 0.2343(2) 0.0325(5) Uani 1 1 d . . . O5 O 0.56586(12) 0.10657(13) 0.8328(2) 0.0311(5) Uani 1 1 d . . . H5A H 0.6012 0.1458 0.7942 0.037 Uiso 1 1 calc R . . N1 N 0.67678(14) 0.16292(15) 0.6312(2) 0.0227(5) Uani 1 1 d . . . N2 N 0.72535(14) 0.22770(15) 0.5492(2) 0.0225(5) Uani 1 1 d . . . H2A H 0.7401 0.2080 0.4556 0.027 Uiso 1 1 calc R . . C1 C 0.56228(17) 0.01630(19) 0.7547(3) 0.0230(6) Uani 1 1 d . . . C2 C 0.50750(19) -0.0579(2) 0.8017(3) 0.0311(7) Uani 1 1 d . . . H2B H 0.4729 -0.0444 0.8851 0.037 Uiso 1 1 calc R . . C3 C 0.50282(19) -0.1510(2) 0.7284(3) 0.0323(7) Uani 1 1 d . . . H3A H 0.4650 -0.2021 0.7619 0.039 Uiso 1 1 calc R . . C4 C 0.55248(19) -0.1720(2) 0.6060(3) 0.0327(7) Uani 1 1 d . . . H4A H 0.5501 -0.2375 0.5572 0.039 Uiso 1 1 calc R . . C5 C 0.60478(18) -0.09732(19) 0.5565(3) 0.0283(7) Uani 1 1 d . . . H5B H 0.6375 -0.1109 0.4703 0.034 Uiso 1 1 calc R . . C6 C 0.61145(17) -0.00226(18) 0.6287(3) 0.0213(6) Uani 1 1 d . . . C7 C 0.66454(17) 0.07468(19) 0.5671(3) 0.0234(6) Uani 1 1 d . . . H7A H 0.6918 0.0593 0.4745 0.028 Uiso 1 1 calc R . . C8 C 0.75059(18) 0.31973(19) 0.6084(3) 0.0218(6) Uani 1 1 d . . . C9 C 0.80222(17) 0.37930(19) 0.5041(3) 0.0211(6) Uani 1 1 d . . . C10 C 0.78587(17) 0.48109(19) 0.4888(3) 0.0238(6) Uani 1 1 d . . . H10A H 0.7463 0.5133 0.5510 0.029 Uiso 1 1 calc R . . C11 C 0.82781(18) 0.53650(18) 0.3816(3) 0.0256(6) Uani 1 1 d . . . C12 C 0.88706(18) 0.4898(2) 0.2941(3) 0.0257(6) Uani 1 1 d . . . C13 C 0.90736(17) 0.38910(19) 0.3189(3) 0.0235(6) Uani 1 1 d . . . C14 C 0.86410(17) 0.33244(19) 0.4224(3) 0.0236(6) Uani 1 1 d . . . H14A H 0.8767 0.2621 0.4374 0.028 Uiso 1 1 calc R . . C15 C 0.7564(2) 0.6882(2) 0.4427(4) 0.0428(8) Uani 1 1 d . . . H15A H 0.7540 0.7603 0.4137 0.064 Uiso 1 1 calc R . . H15C H 0.7805 0.6805 0.5618 0.064 Uiso 1 1 calc R . . H15D H 0.6942 0.6594 0.4150 0.064 Uiso 1 1 calc R . . C16 C 0.8880(2) 0.5328(2) 0.0183(4) 0.0428(8) Uani 1 1 d . . . H16B H 0.9269 0.5647 -0.0509 0.064 Uiso 1 1 calc R . . H16C H 0.8270 0.5649 -0.0032 0.064 Uiso 1 1 calc R . . H16A H 0.8814 0.4605 -0.0081 0.064 Uiso 1 1 calc R . . C17 C 1.00755(19) 0.2543(2) 0.2851(3) 0.0332(7) Uani 1 1 d . . . H17B H 1.0561 0.2377 0.2236 0.050 Uiso 1 1 calc R . . H17C H 0.9588 0.2030 0.2627 0.050 Uiso 1 1 calc R . . H17D H 1.0337 0.2557 0.4041 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0421(12) 0.0308(11) 0.0200(10) 0.0009(8) 0.0151(9) 0.0011(9) O2 0.0426(12) 0.0220(11) 0.0576(13) 0.0017(10) 0.0292(11) 0.0014(9) O3 0.0383(12) 0.0294(11) 0.0410(13) 0.0033(9) 0.0218(10) -0.0072(9) O4 0.0353(11) 0.0285(11) 0.0405(12) 0.0040(9) 0.0238(10) 0.0062(9) O5 0.0407(12) 0.0276(11) 0.0298(11) -0.0038(9) 0.0188(9) -0.0103(9) N1 0.0237(12) 0.0241(13) 0.0216(12) 0.0052(10) 0.0072(10) -0.0031(10) N2 0.0278(13) 0.0248(12) 0.0185(11) -0.0002(10) 0.0133(10) -0.0050(10) C1 0.0295(16) 0.0197(14) 0.0192(14) 0.0004(12) 0.0034(13) -0.0023(12) C2 0.0348(18) 0.0347(17) 0.0248(16) 0.0002(13) 0.0086(14) -0.0092(14) C3 0.0347(17) 0.0312(17) 0.0286(16) 0.0072(13) 0.0006(14) -0.0099(14) C4 0.0386(18) 0.0222(16) 0.0355(17) -0.0035(13) 0.0026(15) -0.0039(14) C5 0.0321(16) 0.0278(16) 0.0262(15) -0.0009(13) 0.0084(13) 0.0019(13) C6 0.0219(14) 0.0229(15) 0.0186(14) 0.0029(11) 0.0026(12) -0.0014(12) C7 0.0248(15) 0.0280(16) 0.0183(14) 0.0009(12) 0.0069(12) 0.0035(12) C8 0.0237(15) 0.0240(15) 0.0185(14) 0.0039(12) 0.0058(12) 0.0025(12) C9 0.0232(15) 0.0228(15) 0.0173(14) -0.0015(11) 0.0040(12) -0.0027(12) C10 0.0240(15) 0.0248(15) 0.0256(15) -0.0047(12) 0.0118(13) -0.0010(12) C11 0.0278(16) 0.0156(14) 0.0346(16) -0.0001(12) 0.0095(14) -0.0023(12) C12 0.0255(15) 0.0249(15) 0.0299(16) 0.0013(12) 0.0132(13) -0.0043(12) C13 0.0210(15) 0.0263(16) 0.0251(15) -0.0022(12) 0.0092(13) 0.0002(12) C14 0.0276(15) 0.0200(14) 0.0243(14) 0.0006(12) 0.0078(13) 0.0012(12) C15 0.0446(19) 0.0277(17) 0.062(2) -0.0072(15) 0.0254(18) -0.0012(15) C16 0.045(2) 0.051(2) 0.0354(19) 0.0151(15) 0.0161(16) -0.0025(16) C17 0.0323(17) 0.0362(18) 0.0337(17) 0.0047(13) 0.0131(14) 0.0115(13) _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 C8 1.238(3) . ? O2 C11 1.356(3) . ? O2 C15 1.413(3) . ? O3 C12 1.376(3) . ? O3 C16 1.421(3) . ? O4 C13 1.358(3) . ? O4 C17 1.421(3) . ? O5 C1 1.349(3) . ? O5 H5A 0.8400 . ? N1 C7 1.277(3) . ? N1 N2 1.375(3) . ? N2 C8 1.334(3) . ? N2 H2A 0.8800 . ? C1 C2 1.373(4) . ? C1 C6 1.399(3) . ? C2 C3 1.365(4) . ? C2 H2B 0.9500 . ? C3 C4 1.386(4) . ? C3 H3A 0.9500 . ? C4 C5 1.363(4) . ? C4 H4A 0.9500 . ? C5 C6 1.383(3) . ? C5 H5B 0.9500 . ? C6 C7 1.435(3) . ? C7 H7A 0.9500 . ? C8 C9 1.481(3) . ? C9 C10 1.366(4) . ? C9 C14 1.382(3) . ? C10 C11 1.383(3) . ? C10 H10A 0.9500 . ? C11 C12 1.383(4) . ? C12 C13 1.369(3) . ? C13 C14 1.381(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15C 0.9800 . ? C15 H15D 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 H16A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17D 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 C11 O2 C15 117.2(2) . . ? C12 O3 C16 113.6(2) . . ? C13 O4 C17 116.70(19) . . ? C1 O5 H5A 109.5 . . ? C7 N1 N2 114.2(2) . . ? C8 N2 N1 121.5(2) . . ? C8 N2 H2A 119.2 . . ? N1 N2 H2A 119.2 . . ? O5 C1 C2 117.8(2) . . ? O5 C1 C6 122.0(2) . . ? C2 C1 C6 120.3(2) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2B 120.0 . . ? C1 C2 H2B 120.0 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5B 119.2 . . ? C6 C5 H5B 119.2 . . ? C5 C6 C1 118.2(2) . . ? C5 C6 C7 119.2(2) . . ? C1 C6 C7 122.5(2) . . ? N1 C7 C6 122.9(2) . . ? N1 C7 H7A 118.6 . . ? C6 C7 H7A 118.6 . . ? O1 C8 N2 123.2(2) . . ? O1 C8 C9 122.5(2) . . ? N2 C8 C9 114.3(2) . . ? C10 C9 C14 121.2(2) . . ? C10 C9 C8 118.2(2) . . ? C14 C9 C8 120.6(2) . . ? C9 C10 C11 119.0(2) . . ? C9 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? O2 C11 C12 115.4(2) . . ? O2 C11 C10 124.3(2) . . ? C12 C11 C10 120.3(2) . . ? C13 C12 O3 119.7(2) . . ? C13 C12 C11 119.8(2) . . ? O3 C12 C11 120.4(2) . . ? O4 C13 C12 115.8(2) . . ? O4 C13 C14 123.9(2) . . ? C12 C13 C14 120.2(2) . . ? C13 C14 C9 119.2(2) . . ? C13 C14 H14A 120.4 . . ? C9 C14 H14A 120.4 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? O2 C15 H15D 109.5 . . ? H15A C15 H15D 109.5 . . ? H15C C15 H15D 109.5 . . ? O3 C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? O4 C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C17 H17D 109.5 . . ? H17B C17 H17D 109.5 . . ? H17C C17 H17D 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 C7 N1 N2 C8 -174.3(2) . . . . ? O5 C1 C2 C3 -178.9(2) . . . . ? C6 C1 C2 C3 1.8(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? C3 C4 C5 C6 1.8(4) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C4 C5 C6 C7 -177.5(2) . . . . ? O5 C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C5 -1.4(4) . . . . ? O5 C1 C6 C7 -3.8(4) . . . . ? C2 C1 C6 C7 175.6(3) . . . . ? N2 N1 C7 C6 -176.6(2) . . . . ? C5 C6 C7 N1 -177.3(2) . . . . ? C1 C6 C7 N1 5.7(4) . . . . ? N1 N2 C8 O1 -0.9(4) . . . . ? N1 N2 C8 C9 -179.9(2) . . . . ? O1 C8 C9 C10 -36.7(4) . . . . ? N2 C8 C9 C10 142.3(2) . . . . ? O1 C8 C9 C14 144.4(3) . . . . ? N2 C8 C9 C14 -36.7(3) . . . . ? C14 C9 C10 C11 4.1(4) . . . . ? C8 C9 C10 C11 -174.8(2) . . . . ? C15 O2 C11 C12 -178.5(2) . . . . ? C15 O2 C11 C10 1.9(4) . . . . ? C9 C10 C11 O2 178.1(2) . . . . ? C9 C10 C11 C12 -1.5(4) . . . . ? C16 O3 C12 C13 81.2(3) . . . . ? C16 O3 C12 C11 -102.0(3) . . . . ? O2 C11 C12 C13 177.6(2) . . . . ? C10 C11 C12 C13 -2.7(4) . . . . ? O2 C11 C12 O3 0.9(4) . . . . ? C10 C11 C12 O3 -179.5(2) . . . . ? C17 O4 C13 C12 166.2(2) . . . . ? C17 O4 C13 C14 -14.9(4) . . . . ? O3 C12 C13 O4 0.1(4) . . . . ? C11 C12 C13 O4 -176.7(2) . . . . ? O3 C12 C13 C14 -178.8(2) . . . . ? C11 C12 C13 C14 4.4(4) . . . . ? O4 C13 C14 C9 179.3(2) . . . . ? C12 C13 C14 C9 -1.8(4) . . . . ? C10 C9 C14 C13 -2.5(4) . . . . ? C8 C9 C14 C13 176.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A N1 0.84 1.92 2.656(3) 145.7 . N2 H2A O1 0.88 1.95 2.793(3) 160.9 4_565 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.234 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.051 #===END