# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_rlm011_0m _database_code_depnum_ccdc_archive 'CCDC 918102' #TrackingRef 'CIFS-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H52 B2 N6 O' _chemical_formula_weight 534.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1297(4) _cell_length_b 9.2734(4) _cell_length_c 19.1974(8) _cell_angle_alpha 79.937(2) _cell_angle_beta 80.421(2) _cell_angle_gamma 73.642(2) _cell_volume 1523.67(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9982 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.39 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9722 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20407 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_unetI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5345 _reflns_number_gt 4283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. constraints were applied to the disordered BCy2 fragments and the B-N and BC distances. ; _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^)+(0.0407P)^2^+1.2139P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5345 _refine_ls_number_parameters 467 _refine_ls_number_restraints 126 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1272 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.192 _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 C11 C 1.4570(3) 0.0492(4) 0.78595(16) 0.0520(8) Uani 1 1 d . . . H11A H 1.5070 -0.0321 0.8210 0.078 Uiso 1 1 calc R . . H11B H 1.4556 0.1477 0.7984 0.078 Uiso 1 1 calc R . . H11C H 1.5142 0.0371 0.7385 0.078 Uiso 1 1 calc R . . C12 C 1.2942(3) 0.0412(3) 0.78583(13) 0.0351(6) Uani 1 1 d . . . H12A H 1.2969 -0.0584 0.7730 0.042 Uiso 1 1 calc R . . H12B H 1.2390 0.0479 0.8346 0.042 Uiso 1 1 calc R . . C5 C 1.2068(2) 0.1637(2) 0.73536(12) 0.0263(5) Uani 1 1 d . . . C4 C 1.2239(2) 0.1839(2) 0.66099(11) 0.0254(5) Uani 1 1 d . . . C15 C 1.3329(3) 0.0920(3) 0.60948(13) 0.0328(6) Uani 1 1 d . . . C16 C 1.3238(3) 0.1478(3) 0.53206(13) 0.0470(7) Uani 1 1 d . . . H16A H 1.3597 0.0616 0.5049 0.071 Uiso 1 1 calc R . . H16B H 1.3886 0.2183 0.5156 0.071 Uiso 1 1 calc R . . H16C H 1.2170 0.2002 0.5249 0.071 Uiso 1 1 calc R . . O15 O 1.4236(2) -0.0244(2) 0.63047(10) 0.0532(6) Uani 1 1 d . . . N4 N 0.8653(2) 0.4705(2) 0.78620(9) 0.0243(4) Uani 1 1 d D A . N5 N 0.7669(2) 0.5596(2) 0.82256(9) 0.0264(4) Uani 1 1 d . . . N6 N 0.6782(2) 0.6382(2) 0.85621(10) 0.0365(5) Uani 1 1 d . . . N1 N 1.0881(2) 0.2795(2) 0.75497(9) 0.0242(4) Uani 1 1 d . . . N2 N 1.0362(2) 0.3618(2) 0.69438(9) 0.0270(4) Uani 1 1 d D A . N3 N 1.1157(2) 0.3075(2) 0.63750(9) 0.0291(4) Uani 1 1 d . . . B1 B 0.9932(3) 0.3341(3) 0.82831(13) 0.0226(5) Uani 1 1 d . . . C21 C 1.0824(2) 0.4126(2) 0.87084(11) 0.0229(5) Uani 1 1 d D . . H21A H 1.0002 0.4773 0.9018 0.027 Uiso 1 1 calc R . . C22 C 1.1887(3) 0.3017(3) 0.92186(13) 0.0313(5) Uani 1 1 d D . . H22A H 1.1285 0.2400 0.9558 0.038 Uiso 1 1 calc R . . H22B H 1.2707 0.2319 0.8940 0.038 Uiso 1 1 calc R . . C23 C 1.2625(3) 0.3820(3) 0.96378(13) 0.0375(6) Uani 1 1 d D . . H23A H 1.1815 0.4412 0.9965 0.045 Uiso 1 1 calc R . . H23B H 1.3350 0.3052 0.9931 0.045 Uiso 1 1 calc R . . C24 C 1.3478(3) 0.4870(3) 0.91563(15) 0.0410(6) Uani 1 1 d D . . H24A H 1.3877 0.5417 0.9450 0.049 Uiso 1 1 calc R . . H24B H 1.4366 0.4267 0.8868 0.049 Uiso 1 1 calc R . . C25 C 1.2434(3) 0.6000(3) 0.86684(17) 0.0507(7) Uani 1 1 d D . . H25A H 1.3033 0.6628 0.8336 0.061 Uiso 1 1 calc R . . H25B H 1.1614 0.6680 0.8955 0.061 Uiso 1 1 calc R . . C26 C 1.1702(3) 0.5202(3) 0.82419(14) 0.0415(6) Uani 1 1 d D . . H26A H 1.2520 0.4619 0.7914 0.050 Uiso 1 1 calc R . . H26B H 1.0986 0.5978 0.7948 0.050 Uiso 1 1 calc R . . C31 C 0.9192(2) 0.2036(2) 0.87482(11) 0.0227(5) Uani 1 1 d . . . H31A H 1.0058 0.1277 0.8973 0.027 Uiso 1 1 calc R . . C32 C 0.8520(3) 0.1139(3) 0.83415(13) 0.0339(6) Uani 1 1 d . . . H32A H 0.7630 0.1830 0.8119 0.041 Uiso 1 1 calc R . . H32B H 0.9307 0.0721 0.7956 0.041 Uiso 1 1 calc R . . C33 C 0.8005(3) -0.0158(3) 0.88327(15) 0.0416(6) Uani 1 1 d . . . H33A H 0.7556 -0.0695 0.8556 0.050 Uiso 1 1 calc R . . H33B H 0.8909 -0.0891 0.9028 0.050 Uiso 1 1 calc R . . C34 C 0.6822(3) 0.0432(3) 0.94433(14) 0.0381(6) Uani 1 1 d . . . H34A H 0.5879 0.1090 0.9251 0.046 Uiso 1 1 calc R . . H34B H 0.6543 -0.0433 0.9766 0.046 Uiso 1 1 calc R . . C35 C 0.7442(3) 0.1326(3) 0.98605(13) 0.0359(6) Uani 1 1 d . . . H35A H 0.8307 0.0638 1.0102 0.043 Uiso 1 1 calc R . . H35B H 0.6624 0.1760 1.0232 0.043 Uiso 1 1 calc R . . C36 C 0.7996(3) 0.2607(3) 0.93716(12) 0.0295(5) Uani 1 1 d . . . H36A H 0.8455 0.3124 0.9654 0.035 Uiso 1 1 calc R . . H36B H 0.7102 0.3360 0.9179 0.035 Uiso 1 1 calc R . . B2 B 0.8868(3) 0.5007(3) 0.69827(13) 0.0423(8) Uani 1 1 d D . . C41A C 0.7388(5) 0.4333(7) 0.6750(2) 0.0207(10) Uani 0.50 1 d PD A 1 H41A H 0.7393 0.3336 0.7050 0.025 Uiso 0.50 1 calc PR A 1 C42A C 0.5764(9) 0.5408(10) 0.6890(5) 0.032(2) Uani 0.50 1 d PD A 1 H42A H 0.5530 0.5480 0.7407 0.039 Uiso 0.50 1 calc PR A 1 H42B H 0.5781 0.6433 0.6640 0.039 Uiso 0.50 1 calc PR A 1 C43A C 0.4471(6) 0.4950(9) 0.6658(3) 0.0347(13) Uani 0.50 1 d PD A 1 H43A H 0.3494 0.5736 0.6743 0.042 Uiso 0.50 1 calc PR A 1 H43B H 0.4353 0.3985 0.6946 0.042 Uiso 0.50 1 calc PR A 1 C44A C 0.4801(5) 0.4756(7) 0.5869(3) 0.0351(12) Uani 0.50 1 d PD A 1 H44A H 0.3964 0.4423 0.5731 0.042 Uiso 0.50 1 calc PR A 1 H44B H 0.4846 0.5738 0.5578 0.042 Uiso 0.50 1 calc PR A 1 C45A C 0.6315(10) 0.3591(13) 0.5732(4) 0.039(2) Uani 0.50 1 d PD A 1 H45A H 0.6531 0.3476 0.5219 0.047 Uiso 0.50 1 calc PR A 1 H45B H 0.6250 0.2598 0.6006 0.047 Uiso 0.50 1 calc PR A 1 C46A C 0.7624(5) 0.4079(6) 0.5953(3) 0.0298(11) Uani 0.50 1 d PD A 1 H46A H 0.7729 0.5032 0.5649 0.036 Uiso 0.50 1 calc PR A 1 H46B H 0.8598 0.3293 0.5863 0.036 Uiso 0.50 1 calc PR A 1 C41B C 0.7598(5) 0.5065(7) 0.6585(3) 0.0266(12) Uani 0.50 1 d PD A 3 H41B H 0.7751 0.5691 0.6113 0.032 Uiso 0.50 1 calc PR A 3 C42B C 0.5996(9) 0.5816(10) 0.6962(6) 0.035(2) Uani 0.50 1 d PD A 3 H42C H 0.5817 0.5222 0.7435 0.042 Uiso 0.50 1 calc PR A 3 H42D H 0.5973 0.6851 0.7038 0.042 Uiso 0.50 1 calc PR A 3 C43B C 0.4737(6) 0.5904(7) 0.6532(4) 0.0443(14) Uani 0.50 1 d PD A 3 H43C H 0.4842 0.6608 0.6086 0.053 Uiso 0.50 1 calc PR A 3 H43D H 0.3731 0.6325 0.6805 0.053 Uiso 0.50 1 calc PR A 3 C44B C 0.4761(6) 0.4388(7) 0.6347(4) 0.0385(14) Uani 0.50 1 d PD A 3 H44C H 0.3998 0.4533 0.6014 0.046 Uiso 0.50 1 calc PR A 3 H44D H 0.4456 0.3747 0.6786 0.046 Uiso 0.50 1 calc PR A 3 C45B C 0.6329(10) 0.3575(12) 0.6009(4) 0.042(2) Uani 0.50 1 d PD A 3 H45C H 0.6542 0.4101 0.5523 0.050 Uiso 0.50 1 calc PR A 3 H45D H 0.6329 0.2527 0.5967 0.050 Uiso 0.50 1 calc PR A 3 C46B C 0.7601(6) 0.3525(6) 0.6448(4) 0.0443(14) Uani 0.50 1 d PD A 3 H46C H 0.7466 0.2878 0.6910 0.053 Uiso 0.50 1 calc PR A 3 H46D H 0.8611 0.3057 0.6191 0.053 Uiso 0.50 1 calc PR A 3 C51A C 0.9636(6) 0.6627(5) 0.6722(2) 0.0215(10) Uani 0.50 1 d PD A 1 H51A H 1.0534 0.6449 0.6991 0.026 Uiso 0.50 1 calc PR A 1 C52A C 0.8528(14) 0.8162(10) 0.6885(7) 0.039(3) Uani 0.50 1 d PD A 1 H52A H 0.7615 0.8358 0.6633 0.047 Uiso 0.50 1 calc PR A 1 H52B H 0.8171 0.8089 0.7403 0.047 Uiso 0.50 1 calc PR A 1 C53A C 0.9235(11) 0.9494(6) 0.6669(3) 0.0389(14) Uani 0.50 1 d PD A 1 H53A H 1.0109 0.9344 0.6941 0.047 Uiso 0.50 1 calc PR A 1 H53B H 0.8461 1.0437 0.6783 0.047 Uiso 0.50 1 calc PR A 1 C54A C 0.9795(6) 0.9645(6) 0.5876(3) 0.0346(12) Uani 0.50 1 d PD A 1 H54A H 1.0285 1.0497 0.5744 0.042 Uiso 0.50 1 calc PR A 1 H54B H 0.8910 0.9867 0.5602 0.042 Uiso 0.50 1 calc PR A 1 C55A C 1.0946(19) 0.8186(11) 0.5691(8) 0.037(3) Uani 0.50 1 d PD A 1 H55A H 1.1869 0.8011 0.5933 0.045 Uiso 0.50 1 calc PR A 1 H55B H 1.1272 0.8279 0.5170 0.045 Uiso 0.50 1 calc PR A 1 C56A C 1.0244(7) 0.6844(6) 0.5918(3) 0.0330(13) Uani 0.50 1 d PD A 1 H56A H 1.1029 0.5909 0.5802 0.040 Uiso 0.50 1 calc PR A 1 H56B H 0.9384 0.6985 0.5638 0.040 Uiso 0.50 1 calc PR A 1 C51B C 0.8928(6) 0.6519(5) 0.6576(3) 0.0259(11) Uani 0.50 1 d PD A 3 H51B H 0.8316 0.6704 0.6168 0.031 Uiso 0.50 1 calc PR A 3 C52B C 0.8223(12) 0.7837(10) 0.7028(6) 0.0270(18) Uani 0.50 1 d PD A 3 H52C H 0.7128 0.7874 0.7194 0.032 Uiso 0.50 1 calc PR A 3 H52D H 0.8767 0.7645 0.7453 0.032 Uiso 0.50 1 calc PR A 3 C53B C 0.8338(7) 0.9341(7) 0.6607(3) 0.0333(12) Uani 0.50 1 d PD A 3 H53C H 0.7901 1.0150 0.6915 0.040 Uiso 0.50 1 calc PR A 3 H53D H 0.7728 0.9570 0.6202 0.040 Uiso 0.50 1 calc PR A 3 C54B C 0.9997(7) 0.9325(6) 0.6327(4) 0.0360(12) Uani 0.50 1 d PD A 3 H54C H 1.0037 1.0312 0.6039 0.043 Uiso 0.50 1 calc PR A 3 H54D H 1.0591 0.9178 0.6733 0.043 Uiso 0.50 1 calc PR A 3 C55B C 1.072(2) 0.8066(12) 0.5873(8) 0.039(3) Uani 0.50 1 d PD A 3 H55C H 1.1817 0.8026 0.5729 0.047 Uiso 0.50 1 calc PR A 3 H55D H 1.0207 0.8289 0.5435 0.047 Uiso 0.50 1 calc PR A 3 C56B C 1.0570(6) 0.6528(6) 0.6268(3) 0.0280(12) Uani 0.50 1 d PD A 3 H56C H 1.1220 0.6233 0.6661 0.034 Uiso 0.50 1 calc PR A 3 H56D H 1.0964 0.5761 0.5937 0.034 Uiso 0.50 1 calc PR A 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 C11 0.0392(15) 0.0596(19) 0.0463(17) -0.0088(14) -0.0146(13) 0.0112(13) C12 0.0367(13) 0.0299(13) 0.0295(13) -0.0045(10) -0.0074(11) 0.0085(11) C5 0.0244(11) 0.0207(11) 0.0299(12) -0.0051(9) -0.0036(9) 0.0012(9) C4 0.0232(11) 0.0243(12) 0.0256(12) -0.0051(9) -0.0019(9) -0.0007(9) C15 0.0272(12) 0.0322(13) 0.0359(14) -0.0109(11) -0.0023(10) 0.0003(10) C16 0.0428(15) 0.0560(18) 0.0311(14) -0.0145(13) 0.0014(12) 0.0068(13) O15 0.0520(12) 0.0466(12) 0.0425(11) -0.0147(9) -0.0064(9) 0.0221(10) N4 0.0251(9) 0.0231(10) 0.0175(9) -0.0045(8) -0.0013(8) 0.0059(8) N5 0.0292(10) 0.0245(10) 0.0183(9) 0.0013(8) -0.0030(8) 0.0021(9) N6 0.0393(12) 0.0316(11) 0.0259(10) -0.0043(9) 0.0036(9) 0.0071(10) N1 0.0248(9) 0.0223(9) 0.0193(9) -0.0007(7) -0.0039(7) 0.0029(7) N2 0.0289(10) 0.0268(10) 0.0168(9) -0.0017(8) -0.0014(8) 0.0048(8) N3 0.0269(10) 0.0317(11) 0.0215(10) -0.0062(8) 0.0011(8) 0.0032(8) B1 0.0205(12) 0.0228(13) 0.0194(12) -0.0015(10) -0.0046(10) 0.0031(10) C21 0.0212(11) 0.0223(11) 0.0221(11) -0.0016(9) -0.0003(9) -0.0031(9) C22 0.0370(13) 0.0274(12) 0.0319(13) -0.0030(10) -0.0130(10) -0.0082(10) C23 0.0384(14) 0.0386(14) 0.0396(14) -0.0106(12) -0.0135(11) -0.0083(11) C24 0.0276(13) 0.0423(15) 0.0582(17) -0.0170(13) -0.0048(12) -0.0116(11) C25 0.0442(16) 0.0369(15) 0.074(2) 0.0064(14) -0.0084(15) -0.0235(13) C26 0.0364(14) 0.0433(15) 0.0437(15) 0.0106(12) -0.0058(12) -0.0180(12) C31 0.0229(11) 0.0215(11) 0.0225(11) -0.0016(9) -0.0072(9) -0.0023(9) C32 0.0334(13) 0.0409(14) 0.0324(13) -0.0127(11) -0.0046(10) -0.0126(11) C33 0.0348(14) 0.0340(14) 0.0618(18) -0.0146(13) -0.0065(12) -0.0133(11) C34 0.0301(13) 0.0297(13) 0.0532(16) 0.0032(12) -0.0029(11) -0.0120(10) C35 0.0379(14) 0.0330(13) 0.0338(13) 0.0025(11) 0.0008(11) -0.0116(11) C36 0.0344(13) 0.0260(12) 0.0263(12) -0.0028(10) 0.0012(10) -0.0084(10) B2 0.0451(17) 0.0422(17) 0.0152(13) -0.0025(12) -0.0017(12) 0.0258(14) C41A 0.031(3) 0.013(3) 0.012(2) 0.003(2) -0.0061(19) 0.004(2) C42A 0.034(4) 0.037(5) 0.023(3) -0.010(3) 0.000(3) -0.003(3) C43A 0.027(3) 0.049(4) 0.030(3) -0.007(3) -0.005(2) -0.011(3) C44A 0.026(3) 0.057(4) 0.023(3) 0.000(3) -0.008(2) -0.012(2) C45A 0.034(4) 0.057(4) 0.033(5) -0.016(4) -0.010(3) -0.013(3) C46A 0.023(2) 0.039(3) 0.023(3) -0.010(2) -0.004(2) 0.003(2) C41B 0.028(3) 0.021(3) 0.026(3) 0.008(2) -0.008(2) -0.002(2) C42B 0.024(3) 0.031(5) 0.051(5) -0.017(3) -0.008(3) 0.001(3) C43B 0.022(3) 0.043(4) 0.070(4) -0.016(3) -0.017(3) 0.000(3) C44B 0.032(3) 0.047(4) 0.045(5) -0.008(4) -0.011(3) -0.019(3) C45B 0.041(4) 0.038(4) 0.054(6) -0.020(5) -0.024(4) -0.003(3) C46B 0.032(3) 0.039(3) 0.066(5) -0.017(4) -0.030(3) 0.003(3) C51A 0.018(3) 0.025(2) 0.017(3) 0.0021(18) -0.005(2) 0.001(2) C52A 0.047(5) 0.036(6) 0.026(5) -0.005(5) 0.016(3) -0.008(4) C53A 0.061(5) 0.027(3) 0.030(4) -0.005(2) 0.006(3) -0.020(3) C54A 0.052(3) 0.029(3) 0.024(3) 0.003(2) -0.006(3) -0.015(2) C55A 0.047(7) 0.028(4) 0.034(6) -0.001(3) 0.003(4) -0.012(3) C56A 0.046(4) 0.026(3) 0.020(3) 0.000(2) 0.006(3) -0.005(3) C51B 0.017(3) 0.034(3) 0.027(3) -0.003(2) -0.007(2) -0.004(2) C52B 0.033(4) 0.019(4) 0.024(5) -0.003(3) 0.003(3) -0.002(3) C53B 0.037(3) 0.018(3) 0.040(3) 0.000(2) 0.004(3) -0.008(2) C54B 0.040(4) 0.031(3) 0.039(4) -0.004(3) 0.004(3) -0.016(3) C55B 0.029(4) 0.044(5) 0.040(7) 0.004(4) 0.006(4) -0.012(3) C56B 0.027(3) 0.027(3) 0.025(3) 0.000(3) 0.003(3) -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 C11 C12 1.509(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C5 1.493(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C5 N1 1.349(3) . ? C5 C4 1.395(3) . ? C4 N3 1.350(3) . ? C4 C15 1.478(3) . ? C15 O15 1.212(3) . ? C15 C16 1.494(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N4 N5 1.246(2) . ? N4 B2 1.650(3) . ? N4 B1 1.656(3) . ? N5 N6 1.124(2) . ? N1 N2 1.352(2) . ? N1 B1 1.608(3) . ? N2 N3 1.302(2) . ? N2 B2 1.593(3) . ? B1 C31 1.613(3) . ? B1 C21 1.620(3) . ? C21 C26 1.529(3) . ? C21 C22 1.536(3) . ? C21 H21A 1.0000 . ? C22 C23 1.526(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.510(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.509(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.528(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C31 C32 1.533(3) . ? C31 C36 1.538(3) . ? C31 H31A 1.0000 . ? C32 C33 1.527(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.520(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.515(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.529(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? B2 C41B 1.474(5) . ? B2 C51B 1.492(5) . ? B2 C41A 1.786(6) . ? B2 C51A 1.793(5) . ? C41A C42A 1.547(9) . ? C41A C46A 1.558(6) . ? C41A H41A 1.0000 . ? C42A C43A 1.514(8) . ? C42A H42A 0.9900 . ? C42A H42B 0.9900 . ? C43A C44A 1.527(7) . ? C43A H43A 0.9900 . ? C43A H43B 0.9900 . ? C44A C45A 1.511(10) . ? C44A H44A 0.9900 . ? C44A H44B 0.9900 . ? C45A C46A 1.534(9) . ? C45A H45A 0.9900 . ? C45A H45B 0.9900 . ? C46A H46A 0.9900 . ? C46A H46B 0.9900 . ? C41B C46B 1.496(7) . ? C41B C42B 1.548(9) . ? C41B C51B 2.049(8) . ? C41B H41B 1.0000 . ? C42B C43B 1.500(9) . ? C42B H42C 0.9900 . ? C42B H42D 0.9900 . ? C43B C44B 1.502(7) . ? C43B H43C 0.9900 . ? C43B H43D 0.9900 . ? C44B C45B 1.514(10) . ? C44B H44C 0.9900 . ? C44B H44D 0.9900 . ? C45B C46B 1.530(8) . ? C45B H45C 0.9900 . ? C45B H45D 0.9900 . ? C46B H46C 0.9900 . ? C46B H46D 0.9900 . ? C51A C52A 1.545(10) . ? C51A C56A 1.550(6) . ? C51A H51A 1.0000 . ? C52A C53A 1.515(9) . ? C52A H52A 0.9900 . ? C52A H52B 0.9900 . ? C53A C54A 1.519(7) . ? C53A H53A 0.9900 . ? C53A H53B 0.9900 . ? C54A C55A 1.518(11) . ? C54A H54A 0.9900 . ? C54A H54B 0.9900 . ? C55A C56A 1.522(11) . ? C55A H55A 0.9900 . ? C55A H55B 0.9900 . ? C56A H56A 0.9900 . ? C56A H56B 0.9900 . ? C51B C56B 1.519(7) . ? C51B C52B 1.550(9) . ? C51B H51B 1.0000 . ? C52B C53B 1.506(8) . ? C52B H52C 0.9900 . ? C52B H52D 0.9900 . ? C53B C54B 1.518(7) . ? C53B H53C 0.9900 . ? C53B H53D 0.9900 . ? C54B C55B 1.512(11) . ? C54B H54C 0.9900 . ? C54B H54D 0.9900 . ? C55B C56B 1.524(10) . ? C55B H55C 0.9900 . ? C55B H55D 0.9900 . ? C56B H56C 0.9900 . ? C56B H56D 0.9900 . ? 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 C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 C11 113.5(2) . . ? C5 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C5 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N1 C5 C4 105.53(18) . . ? N1 C5 C12 124.8(2) . . ? C4 C5 C12 129.6(2) . . ? N3 C4 C5 109.37(18) . . ? N3 C4 C15 120.04(19) . . ? C5 C4 C15 130.6(2) . . ? O15 C15 C4 120.2(2) . . ? O15 C15 C16 122.6(2) . . ? C4 C15 C16 117.2(2) . . ? 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 . . ? N5 N4 B2 121.79(17) . . ? N5 N4 B1 117.77(16) . . ? B2 N4 B1 119.77(16) . . ? N6 N5 N4 178.9(2) . . ? C5 N1 N2 106.91(17) . . ? C5 N1 B1 136.96(18) . . ? N2 N1 B1 116.01(16) . . ? N3 N2 N1 112.28(16) . . ? N3 N2 B2 127.39(17) . . ? N1 N2 B2 120.20(16) . . ? N2 N3 C4 105.89(17) . . ? N1 B1 C31 110.85(17) . . ? N1 B1 C21 114.39(18) . . ? C31 B1 C21 116.10(17) . . ? N1 B1 N4 92.61(14) . . ? C31 B1 N4 112.46(17) . . ? C21 B1 N4 108.04(17) . . ? C26 C21 C22 109.08(18) . . ? C26 C21 B1 115.27(19) . . ? C22 C21 B1 114.86(17) . . ? C26 C21 H21A 105.6 . . ? C22 C21 H21A 105.6 . . ? B1 C21 H21A 105.6 . . ? C23 C22 C21 112.74(19) . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22B 109.0 . . ? C21 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C22 112.2(2) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 110.8(2) . . ? C25 C24 H24A 109.5 . . ? C23 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C24 C25 C26 111.3(2) . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C21 113.5(2) . . ? C25 C26 H26A 108.9 . . ? C21 C26 H26A 108.9 . . ? C25 C26 H26B 108.9 . . ? C21 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? C32 C31 C36 109.01(18) . . ? C32 C31 B1 117.01(18) . . ? C36 C31 B1 113.01(17) . . ? C32 C31 H31A 105.6 . . ? C36 C31 H31A 105.6 . . ? B1 C31 H31A 105.6 . . ? C33 C32 C31 111.6(2) . . ? C33 C32 H32A 109.3 . . ? C31 C32 H32A 109.3 . . ? C33 C32 H32B 109.3 . . ? C31 C32 H32B 109.3 . . ? H32A C32 H32B 108.0 . . ? C34 C33 C32 111.0(2) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 C34 C33 111.1(2) . . ? C35 C34 H34A 109.4 . . ? C33 C34 H34A 109.4 . . ? C35 C34 H34B 109.4 . . ? C33 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C36 111.1(2) . . ? C34 C35 H35A 109.4 . . ? C36 C35 H35A 109.4 . . ? C34 C35 H35B 109.4 . . ? C36 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C31 112.61(18) . . ? C35 C36 H36A 109.1 . . ? C31 C36 H36A 109.1 . . ? C35 C36 H36B 109.1 . . ? C31 C36 H36B 109.1 . . ? H36A C36 H36B 107.8 . . ? C41B B2 C51B 87.4(4) . . ? C41B B2 N2 119.1(3) . . ? C51B B2 N2 119.6(3) . . ? C41B B2 N4 120.5(3) . . ? C51B B2 N4 122.2(3) . . ? N2 B2 N4 91.31(15) . . ? C41B B2 C41A 24.6(2) . . ? C51B B2 C41A 112.0(3) . . ? N2 B2 C41A 104.9(2) . . ? N4 B2 C41A 103.8(2) . . ? C41B B2 C51A 112.9(3) . . ? C51B B2 C51A 25.6(2) . . ? N2 B2 C51A 103.1(2) . . ? N4 B2 C51A 106.9(2) . . ? C41A B2 C51A 137.5(3) . . ? C42A C41A C46A 106.8(5) . . ? C42A C41A B2 113.1(4) . . ? C46A C41A B2 113.4(4) . . ? C42A C41A H41A 107.8 . . ? C46A C41A H41A 107.8 . . ? B2 C41A H41A 107.8 . . ? C43A C42A C41A 115.6(6) . . ? C43A C42A H42A 108.4 . . ? C41A C42A H42A 108.4 . . ? C43A C42A H42B 108.4 . . ? C41A C42A H42B 108.4 . . ? H42A C42A H42B 107.4 . . ? C42A C43A C44A 110.7(5) . . ? C42A C43A H43A 109.5 . . ? C44A C43A H43A 109.5 . . ? C42A C43A H43B 109.5 . . ? C44A C43A H43B 109.5 . . ? H43A C43A H43B 108.1 . . ? C45A C44A C43A 109.8(5) . . ? C45A C44A H44A 109.7 . . ? C43A C44A H44A 109.7 . . ? C45A C44A H44B 109.7 . . ? C43A C44A H44B 109.7 . . ? H44A C44A H44B 108.2 . . ? C44A C45A C46A 110.4(7) . . ? C44A C45A H45A 109.6 . . ? C46A C45A H45A 109.6 . . ? C44A C45A H45B 109.6 . . ? C46A C45A H45B 109.6 . . ? H45A C45A H45B 108.1 . . ? C45A C46A C41A 114.1(5) . . ? C45A C46A H46A 108.7 . . ? C41A C46A H46A 108.7 . . ? C45A C46A H46B 108.7 . . ? C41A C46A H46B 108.7 . . ? H46A C46A H46B 107.6 . . ? B2 C41B C46B 112.0(4) . . ? B2 C41B C42B 113.0(5) . . ? C46B C41B C42B 108.9(5) . . ? B2 C41B C51B 46.7(2) . . ? C46B C41B C51B 145.1(4) . . ? C42B C41B C51B 105.5(4) . . ? B2 C41B H41B 107.6 . . ? C46B C41B H41B 107.6 . . ? C42B C41B H41B 107.6 . . ? C51B C41B H41B 66.4 . . ? C43B C42B C41B 111.6(7) . . ? C43B C42B H42C 109.3 . . ? C41B C42B H42C 109.3 . . ? C43B C42B H42D 109.3 . . ? C41B C42B H42D 109.3 . . ? H42C C42B H42D 108.0 . . ? C42B C43B C44B 112.7(5) . . ? C42B C43B H43C 109.0 . . ? C44B C43B H43C 109.0 . . ? C42B C43B H43D 109.0 . . ? C44B C43B H43D 109.0 . . ? H43C C43B H43D 107.8 . . ? C43B C44B C45B 112.4(6) . . ? C43B C44B H44C 109.1 . . ? C45B C44B H44C 109.1 . . ? C43B C44B H44D 109.1 . . ? C45B C44B H44D 109.1 . . ? H44C C44B H44D 107.8 . . ? C44B C45B C46B 111.7(6) . . ? C44B C45B H45C 109.3 . . ? C46B C45B H45C 109.3 . . ? C44B C45B H45D 109.3 . . ? C46B C45B H45D 109.3 . . ? H45C C45B H45D 107.9 . . ? C41B C46B C45B 112.6(6) . . ? C41B C46B H46C 109.1 . . ? C45B C46B H46C 109.1 . . ? C41B C46B H46D 109.1 . . ? C45B C46B H46D 109.1 . . ? H46C C46B H46D 107.8 . . ? C52A C51A C56A 106.4(5) . . ? C52A C51A B2 115.8(4) . . ? C56A C51A B2 113.1(4) . . ? C52A C51A H51A 107.0 . . ? C56A C51A H51A 107.0 . . ? B2 C51A H51A 107.0 . . ? C53A C52A C51A 114.0(7) . . ? C53A C52A H52A 108.8 . . ? C51A C52A H52A 108.8 . . ? C53A C52A H52B 108.8 . . ? C51A C52A H52B 108.8 . . ? H52A C52A H52B 107.7 . . ? C52A C53A C54A 110.3(6) . . ? C52A C53A H53A 109.6 . . ? C54A C53A H53A 109.6 . . ? C52A C53A H53B 109.6 . . ? C54A C53A H53B 109.6 . . ? H53A C53A H53B 108.1 . . ? C53A C54A C55A 110.1(7) . . ? C53A C54A H54A 109.6 . . ? C55A C54A H54A 109.6 . . ? C53A C54A H54B 109.6 . . ? C55A C54A H54B 109.6 . . ? H54A C54A H54B 108.2 . . ? C54A C55A C56A 110.7(9) . . ? C54A C55A H55A 109.5 . . ? C56A C55A H55A 109.5 . . ? C54A C55A H55B 109.5 . . ? C56A C55A H55B 109.5 . . ? H55A C55A H55B 108.1 . . ? C55A C56A C51A 113.9(7) . . ? C55A C56A H56A 108.8 . . ? C51A C56A H56A 108.8 . . ? C55A C56A H56B 108.8 . . ? C51A C56A H56B 108.8 . . ? H56A C56A H56B 107.7 . . ? B2 C51B C56B 110.7(4) . . ? B2 C51B C52B 113.0(5) . . ? C56B C51B C52B 109.8(5) . . ? B2 C51B C41B 45.9(2) . . ? C56B C51B C41B 133.7(4) . . ? C52B C51B C41B 116.2(5) . . ? B2 C51B H51B 107.7 . . ? C56B C51B H51B 107.7 . . ? C52B C51B H51B 107.7 . . ? C41B C51B H51B 63.1 . . ? C53B C52B C51B 111.6(7) . . ? C53B C52B H52C 109.3 . . ? C51B C52B H52C 109.3 . . ? C53B C52B H52D 109.3 . . ? C51B C52B H52D 109.3 . . ? H52C C52B H52D 108.0 . . ? C52B C53B C54B 111.2(5) . . ? C52B C53B H53C 109.4 . . ? C54B C53B H53C 109.4 . . ? C52B C53B H53D 109.4 . . ? C54B C53B H53D 109.4 . . ? H53C C53B H53D 108.0 . . ? C55B C54B C53B 110.7(7) . . ? C55B C54B H54C 109.5 . . ? C53B C54B H54C 109.5 . . ? C55B C54B H54D 109.5 . . ? C53B C54B H54D 109.5 . . ? H54C C54B H54D 108.1 . . ? C54B C55B C56B 112.0(7) . . ? C54B C55B H55C 109.2 . . ? C56B C55B H55C 109.2 . . ? C54B C55B H55D 109.2 . . ? C56B C55B H55D 109.2 . . ? H55C C55B H55D 107.9 . . ? C55B C56B C51B 113.2(7) . . ? C55B C56B H56C 108.9 . . ? C51B C56B H56C 108.9 . . ? C55B C56B H56D 108.9 . . ? C51B C56B H56D 108.9 . . ? H56C C56B H56D 107.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.233 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.041 data_rlm56 _database_code_depnum_ccdc_archive 'CCDC 918103' #TrackingRef 'CIFS-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H55 B2 N6 O P' _chemical_formula_weight 664.47 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5954(13) _cell_length_b 11.2785(15) _cell_length_c 17.351(2) _cell_angle_alpha 97.004(4) _cell_angle_beta 97.151(4) _cell_angle_gamma 101.004(5) _cell_volume 1808.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9894 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9542 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17751 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0440 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6296 _reflns_number_gt 5399 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+1.8625P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6296 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 P1 P 0.86079(6) 0.66232(5) 0.48120(3) 0.01326(15) Uani 1 1 d . . . O1 O 0.83017(17) 0.53952(14) 0.50563(9) 0.0177(4) Uani 1 1 d . . . N4 N 1.0624(2) 0.60095(17) 0.16274(11) 0.0145(4) Uani 1 1 d . . . C4 C 0.9295(2) 0.6493(2) 0.38880(13) 0.0145(5) Uani 1 1 d . . . B2 B 0.9979(3) 0.7219(2) 0.19193(15) 0.0154(6) Uani 1 1 d . . . N5 N 1.1154(2) 0.58837(18) 0.10126(12) 0.0184(4) Uani 1 1 d . . . C5 C 0.9963(2) 0.5573(2) 0.36257(13) 0.0155(5) Uani 1 1 d . . . H2 H 1.0174 0.4933 0.3899 0.019 Uiso 1 1 calc R . . B1 B 1.0730(3) 0.4971(2) 0.22113(15) 0.0149(6) Uani 1 1 d . . . N6 N 1.1644(3) 0.5731(2) 0.04600(13) 0.0305(5) Uani 1 1 d . . . N1 N 1.0253(2) 0.57596(17) 0.29130(11) 0.0137(4) Uani 1 1 d . . . N2 N 0.9770(2) 0.67589(16) 0.27470(11) 0.0140(4) Uani 1 1 d . . . N3 N 0.9195(2) 0.72264(17) 0.33274(11) 0.0156(4) Uani 1 1 d . . . C11 C 0.8432(3) 0.7146(2) 0.14073(13) 0.0170(5) Uani 1 1 d . . . H11A H 0.7829 0.6327 0.1431 0.020 Uiso 1 1 calc R . . C12 C 0.8511(3) 0.7229(3) 0.05358(14) 0.0276(6) Uani 1 1 d . . . H12A H 0.9099 0.8033 0.0491 0.033 Uiso 1 1 calc R . . H12B H 0.8995 0.6590 0.0320 0.033 Uiso 1 1 calc R . . C13 C 0.7036(3) 0.7072(3) 0.00509(16) 0.0371(7) Uani 1 1 d . . . H13A H 0.7145 0.7154 -0.0501 0.044 Uiso 1 1 calc R . . H13B H 0.6469 0.6244 0.0060 0.044 Uiso 1 1 calc R . . C14 C 0.6248(3) 0.8018(3) 0.03715(16) 0.0370(7) Uani 1 1 d . . . H14A H 0.5271 0.7869 0.0068 0.044 Uiso 1 1 calc R . . H14B H 0.6763 0.8842 0.0312 0.044 Uiso 1 1 calc R . . C15 C 0.6141(3) 0.7963(3) 0.12356(16) 0.0324(7) Uani 1 1 d . . . H15A H 0.5674 0.8620 0.1441 0.039 Uiso 1 1 calc R . . H15B H 0.5536 0.7170 0.1288 0.039 Uiso 1 1 calc R . . C16 C 0.7622(3) 0.8109(2) 0.17197(14) 0.0221(6) Uani 1 1 d . . . H16A H 0.7512 0.8036 0.2273 0.027 Uiso 1 1 calc R . . H16B H 0.8194 0.8934 0.1708 0.027 Uiso 1 1 calc R . . C21 C 1.1145(2) 0.8504(2) 0.20421(14) 0.0172(5) Uani 1 1 d . . . H21A H 1.0569 0.9149 0.1989 0.021 Uiso 1 1 calc R . . C22 C 1.2132(3) 0.8613(2) 0.14054(15) 0.0222(6) Uani 1 1 d . . . H22A H 1.2742 0.7999 0.1437 0.027 Uiso 1 1 calc R . . H22B H 1.1532 0.8427 0.0881 0.027 Uiso 1 1 calc R . . C23 C 1.3098(3) 0.9886(2) 0.14903(17) 0.0306(6) Uani 1 1 d . . . H23A H 1.3742 0.9897 0.1087 0.037 Uiso 1 1 calc R . . H23B H 1.2497 1.0495 0.1405 0.037 Uiso 1 1 calc R . . C24 C 1.3990(3) 1.0224(2) 0.23036(17) 0.0291(6) Uani 1 1 d . . . H24A H 1.4659 0.9662 0.2368 0.035 Uiso 1 1 calc R . . H24B H 1.4569 1.1064 0.2359 0.035 Uiso 1 1 calc R . . C25 C 1.3037(3) 1.0149(2) 0.29392(16) 0.0258(6) Uani 1 1 d . . . H25A H 1.2428 1.0763 0.2903 0.031 Uiso 1 1 calc R . . H25B H 1.3644 1.0342 0.3461 0.031 Uiso 1 1 calc R . . C26 C 1.2079(3) 0.8875(2) 0.28569(14) 0.0200(5) Uani 1 1 d . . . H26A H 1.1448 0.8863 0.3267 0.024 Uiso 1 1 calc R . . H26B H 1.2688 0.8272 0.2940 0.024 Uiso 1 1 calc R . . C31 C 0.9512(2) 0.3739(2) 0.19367(13) 0.0164(5) Uani 1 1 d . . . H31A H 0.9469 0.3311 0.2408 0.020 Uiso 1 1 calc R . . C32 C 0.7981(3) 0.3919(2) 0.16929(14) 0.0199(5) Uani 1 1 d . . . H32A H 0.7722 0.4467 0.2118 0.024 Uiso 1 1 calc R . . H32B H 0.7956 0.4323 0.1217 0.024 Uiso 1 1 calc R . . C33 C 0.6871(3) 0.2719(2) 0.15240(15) 0.0250(6) Uani 1 1 d . . . H33A H 0.6817 0.2355 0.2013 0.030 Uiso 1 1 calc R . . H33B H 0.5915 0.2881 0.1344 0.030 Uiso 1 1 calc R . . C34 C 0.7256(3) 0.1823(2) 0.09007(16) 0.0297(6) Uani 1 1 d . . . H34A H 0.7179 0.2138 0.0392 0.036 Uiso 1 1 calc R . . H34B H 0.6566 0.1031 0.0836 0.036 Uiso 1 1 calc R . . C35 C 0.8771(3) 0.1626(2) 0.11182(16) 0.0261(6) Uani 1 1 d . . . H35A H 0.9016 0.1094 0.0680 0.031 Uiso 1 1 calc R . . H35B H 0.8812 0.1206 0.1587 0.031 Uiso 1 1 calc R . . C36 C 0.9865(3) 0.2832(2) 0.12913(14) 0.0208(5) Uani 1 1 d . . . H36A H 0.9898 0.3205 0.0804 0.025 Uiso 1 1 calc R . . H36B H 1.0828 0.2671 0.1457 0.025 Uiso 1 1 calc R . . C41 C 1.2349(2) 0.4761(2) 0.23587(13) 0.0159(5) Uani 1 1 d . . . H41A H 1.2531 0.4387 0.1838 0.019 Uiso 1 1 calc R . . C42 C 1.3560(3) 0.5895(2) 0.26184(15) 0.0215(5) Uani 1 1 d . . . H42A H 1.3472 0.6279 0.3150 0.026 Uiso 1 1 calc R . . H42B H 1.3461 0.6494 0.2254 0.026 Uiso 1 1 calc R . . C43 C 1.5041(3) 0.5579(2) 0.26322(16) 0.0252(6) Uani 1 1 d . . . H43A H 1.5169 0.5278 0.2091 0.030 Uiso 1 1 calc R . . H43B H 1.5790 0.6325 0.2829 0.030 Uiso 1 1 calc R . . C44 C 1.5228(3) 0.4604(2) 0.31548(15) 0.0243(6) Uani 1 1 d . . . H44A H 1.6155 0.4361 0.3107 0.029 Uiso 1 1 calc R . . H44B H 1.5250 0.4949 0.3710 0.029 Uiso 1 1 calc R . . C45 C 1.4015(3) 0.3487(2) 0.29259(15) 0.0218(6) Uani 1 1 d . . . H45A H 1.4120 0.2907 0.3303 0.026 Uiso 1 1 calc R . . H45B H 1.4080 0.3076 0.2398 0.026 Uiso 1 1 calc R . . C46 C 1.2549(3) 0.3821(2) 0.29174(14) 0.0186(5) Uani 1 1 d . . . H46A H 1.2449 0.4165 0.3456 0.022 Uiso 1 1 calc R . . H46B H 1.1788 0.3074 0.2747 0.022 Uiso 1 1 calc R . . C51 C 0.7056(2) 0.7287(2) 0.46908(13) 0.0166(5) Uani 1 1 d . . . C52 C 0.6996(3) 0.8343(2) 0.43549(15) 0.0230(6) Uani 1 1 d . . . H52 H 0.7807 0.8753 0.4159 0.028 Uiso 1 1 calc R . . C53 C 0.5749(3) 0.8787(3) 0.43105(16) 0.0299(6) Uani 1 1 d . . . H53 H 0.5707 0.9509 0.4086 0.036 Uiso 1 1 calc R . . C54 C 0.4553(3) 0.8187(3) 0.45905(15) 0.0292(6) Uani 1 1 d . . . H54 H 0.3699 0.8500 0.4558 0.035 Uiso 1 1 calc R . . C55 C 0.4606(3) 0.7135(3) 0.49164(15) 0.0274(6) Uani 1 1 d . . . H55 H 0.3784 0.6717 0.5100 0.033 Uiso 1 1 calc R . . C56 C 0.5857(3) 0.6693(2) 0.49748(14) 0.0209(5) Uani 1 1 d . . . H56 H 0.5900 0.5981 0.5210 0.025 Uiso 1 1 calc R . . C61 C 0.9958(2) 0.7682(2) 0.55124(13) 0.0150(5) Uani 1 1 d . . . C62 C 1.1279(3) 0.7366(2) 0.56903(14) 0.0211(5) Uani 1 1 d . . . H62 H 1.1480 0.6664 0.5401 0.025 Uiso 1 1 calc R . . C63 C 1.2301(3) 0.8067(2) 0.62855(15) 0.0246(6) Uani 1 1 d . . . H63 H 1.3205 0.7850 0.6403 0.030 Uiso 1 1 calc R . . C64 C 1.2009(3) 0.9087(2) 0.67111(14) 0.0231(6) Uani 1 1 d . . . H64 H 1.2711 0.9568 0.7122 0.028 Uiso 1 1 calc R . . C65 C 1.0707(3) 0.9405(2) 0.65404(15) 0.0249(6) Uani 1 1 d . . . H65 H 1.0511 1.0107 0.6833 0.030 Uiso 1 1 calc R . . C66 C 0.9679(3) 0.8710(2) 0.59440(14) 0.0219(6) Uani 1 1 d . . . H66 H 0.8780 0.8935 0.5829 0.026 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 P1 0.0140(3) 0.0149(3) 0.0123(3) 0.0027(2) 0.0041(2) 0.0048(2) O1 0.0205(9) 0.0167(9) 0.0183(9) 0.0052(7) 0.0063(7) 0.0057(7) N4 0.0174(10) 0.0174(10) 0.0123(10) 0.0043(8) 0.0079(8) 0.0073(8) C4 0.0133(12) 0.0180(12) 0.0118(11) 0.0021(9) 0.0019(9) 0.0025(9) B2 0.0182(14) 0.0165(14) 0.0136(13) 0.0017(11) 0.0058(11) 0.0070(11) N5 0.0220(11) 0.0169(11) 0.0178(11) 0.0035(8) 0.0040(9) 0.0069(9) C5 0.0181(12) 0.0167(12) 0.0129(12) 0.0048(9) 0.0034(9) 0.0046(10) B1 0.0183(14) 0.0161(14) 0.0119(13) 0.0033(10) 0.0044(11) 0.0055(11) N6 0.0453(15) 0.0311(13) 0.0230(12) 0.0081(10) 0.0179(11) 0.0170(11) N1 0.0141(10) 0.0130(10) 0.0148(10) 0.0016(8) 0.0025(8) 0.0046(8) N2 0.0168(10) 0.0115(10) 0.0146(10) 0.0022(8) 0.0030(8) 0.0043(8) N3 0.0169(10) 0.0165(10) 0.0134(10) 0.0005(8) 0.0054(8) 0.0026(8) C11 0.0195(13) 0.0145(12) 0.0178(12) 0.0033(9) 0.0042(10) 0.0044(10) C12 0.0247(14) 0.0418(17) 0.0193(13) 0.0029(12) 0.0015(11) 0.0164(12) C13 0.0346(17) 0.057(2) 0.0209(14) -0.0029(13) -0.0025(12) 0.0224(15) C14 0.0320(16) 0.0525(19) 0.0292(16) 0.0042(14) -0.0047(13) 0.0227(14) C15 0.0260(15) 0.0459(18) 0.0307(15) 0.0045(13) 0.0055(12) 0.0205(13) C16 0.0231(14) 0.0250(14) 0.0200(13) 0.0007(11) 0.0034(11) 0.0108(11) C21 0.0182(13) 0.0156(12) 0.0196(12) 0.0036(10) 0.0048(10) 0.0060(10) C22 0.0218(13) 0.0227(13) 0.0230(13) 0.0060(11) 0.0073(11) 0.0026(11) C23 0.0274(15) 0.0239(14) 0.0435(17) 0.0100(12) 0.0172(13) 0.0024(12) C24 0.0190(14) 0.0191(14) 0.0474(17) -0.0004(12) 0.0095(12) 0.0004(11) C25 0.0184(13) 0.0210(14) 0.0351(15) -0.0030(11) 0.0016(11) 0.0033(11) C26 0.0188(13) 0.0173(13) 0.0230(13) 0.0017(10) 0.0023(10) 0.0031(10) C31 0.0196(13) 0.0155(12) 0.0158(12) 0.0047(9) 0.0042(10) 0.0055(10) C32 0.0202(13) 0.0191(13) 0.0214(13) 0.0021(10) 0.0059(10) 0.0052(10) C33 0.0197(13) 0.0270(14) 0.0277(14) 0.0050(11) 0.0045(11) 0.0018(11) C34 0.0259(15) 0.0232(14) 0.0341(16) -0.0042(12) -0.0010(12) -0.0006(11) C35 0.0271(15) 0.0194(13) 0.0295(15) -0.0030(11) 0.0037(12) 0.0037(11) C36 0.0217(13) 0.0208(13) 0.0205(13) 0.0006(10) 0.0049(10) 0.0061(10) C41 0.0193(13) 0.0159(12) 0.0137(12) 0.0016(9) 0.0054(10) 0.0056(10) C42 0.0213(13) 0.0172(13) 0.0261(14) 0.0045(10) 0.0014(11) 0.0048(10) C43 0.0152(13) 0.0252(14) 0.0350(15) 0.0066(12) 0.0035(11) 0.0027(11) C44 0.0157(13) 0.0290(15) 0.0293(14) 0.0039(11) 0.0012(11) 0.0088(11) C45 0.0239(14) 0.0217(13) 0.0217(13) 0.0035(10) 0.0026(11) 0.0099(11) C46 0.0214(13) 0.0172(12) 0.0187(12) 0.0044(10) 0.0043(10) 0.0060(10) C51 0.0156(12) 0.0194(12) 0.0145(12) -0.0013(10) 0.0019(9) 0.0058(10) C52 0.0212(13) 0.0253(14) 0.0257(14) 0.0084(11) 0.0063(11) 0.0080(11) C53 0.0325(16) 0.0321(16) 0.0314(15) 0.0105(12) 0.0065(12) 0.0180(13) C54 0.0207(14) 0.0418(17) 0.0282(15) -0.0011(12) 0.0012(11) 0.0195(12) C55 0.0168(13) 0.0371(16) 0.0282(14) 0.0002(12) 0.0067(11) 0.0060(12) C56 0.0178(13) 0.0215(13) 0.0227(13) 0.0017(10) 0.0035(10) 0.0028(10) C61 0.0172(12) 0.0152(12) 0.0130(11) 0.0037(9) 0.0045(9) 0.0023(9) C62 0.0196(13) 0.0198(13) 0.0243(13) -0.0011(10) 0.0059(11) 0.0063(10) C63 0.0176(13) 0.0274(14) 0.0282(14) 0.0022(11) 0.0002(11) 0.0064(11) C64 0.0210(14) 0.0256(14) 0.0190(13) 0.0008(11) -0.0016(10) 0.0001(11) C65 0.0270(14) 0.0213(14) 0.0253(14) -0.0036(11) 0.0036(11) 0.0070(11) C66 0.0219(13) 0.0217(13) 0.0231(13) 0.0011(10) 0.0022(11) 0.0093(11) _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 P1 O1 1.4844(17) . ? P1 C51 1.791(2) . ? P1 C61 1.801(2) . ? P1 C4 1.808(2) . ? N4 N5 1.242(3) . ? N4 B1 1.649(3) . ? N4 B2 1.653(3) . ? C4 N3 1.358(3) . ? C4 C5 1.380(3) . ? B2 N2 1.608(3) . ? B2 C11 1.615(3) . ? B2 C21 1.626(4) . ? N5 N6 1.128(3) . ? C5 N1 1.333(3) . ? C5 H2 0.9500 . ? B1 N1 1.585(3) . ? B1 C41 1.610(3) . ? B1 C31 1.613(4) . ? N1 N2 1.346(3) . ? N2 N3 1.311(3) . ? C11 C16 1.537(3) . ? C11 C12 1.537(3) . ? C11 H11A 1.0000 . ? C12 C13 1.521(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.512(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.523(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.527(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C21 C26 1.540(3) . ? C21 C22 1.543(3) . ? C21 H21A 1.0000 . ? C22 C23 1.532(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.521(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.518(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.532(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C31 C32 1.536(3) . ? C31 C36 1.537(3) . ? C31 H31A 1.0000 . ? C32 C33 1.526(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.518(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.520(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.523(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C41 C42 1.533(3) . ? C41 C46 1.543(3) . ? C41 H41A 1.0000 . ? C42 C43 1.528(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.530(4) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.517(4) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.523(3) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C51 C52 1.396(3) . ? C51 C56 1.394(3) . ? C52 C53 1.380(4) . ? C52 H52 0.9500 . ? C53 C54 1.391(4) . ? C53 H53 0.9500 . ? C54 C55 1.382(4) . ? C54 H54 0.9500 . ? C55 C56 1.382(4) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C61 C62 1.389(3) . ? C61 C66 1.391(3) . ? C62 C63 1.381(3) . ? C62 H62 0.9500 . ? C63 C64 1.383(4) . ? C63 H63 0.9500 . ? C64 C65 1.372(4) . ? C64 H64 0.9500 . ? C65 C66 1.382(4) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C51 113.12(11) . . ? O1 P1 C61 111.73(10) . . ? C51 P1 C61 107.26(11) . . ? O1 P1 C4 108.69(10) . . ? C51 P1 C4 108.51(11) . . ? C61 P1 C4 107.32(10) . . ? N5 N4 B1 117.07(18) . . ? N5 N4 B2 123.26(18) . . ? B1 N4 B2 119.39(17) . . ? N3 C4 C5 108.76(19) . . ? N3 C4 P1 126.85(17) . . ? C5 C4 P1 124.33(17) . . ? N2 B2 C11 109.90(19) . . ? N2 B2 C21 111.06(18) . . ? C11 B2 C21 117.7(2) . . ? N2 B2 N4 91.09(16) . . ? C11 B2 N4 109.94(18) . . ? C21 B2 N4 114.01(19) . . ? N6 N5 N4 177.6(2) . . ? N1 C5 C4 106.5(2) . . ? N1 C5 H2 126.8 . . ? C4 C5 H2 126.8 . . ? N1 B1 C41 115.73(19) . . ? N1 B1 C31 108.15(18) . . ? C41 B1 C31 114.83(19) . . ? N1 B1 N4 92.88(16) . . ? C41 B1 N4 110.11(18) . . ? C31 B1 N4 113.23(19) . . ? C5 N1 N2 107.49(18) . . ? C5 N1 B1 134.60(19) . . ? N2 N1 B1 116.69(17) . . ? N3 N2 N1 111.39(17) . . ? N3 N2 B2 129.63(18) . . ? N1 N2 B2 118.97(17) . . ? N2 N3 C4 105.89(18) . . ? C16 C11 C12 108.14(19) . . ? C16 C11 B2 114.15(19) . . ? C12 C11 B2 113.14(19) . . ? C16 C11 H11A 107.0 . . ? C12 C11 H11A 107.0 . . ? B2 C11 H11A 107.0 . . ? C13 C12 C11 112.5(2) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 110.8(2) . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 110.7(2) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 111.3(2) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C11 111.9(2) . . ? C15 C16 H16A 109.2 . . ? C11 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C11 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C26 C21 C22 108.84(19) . . ? C26 C21 B2 115.82(19) . . ? C22 C21 B2 114.36(19) . . ? C26 C21 H21A 105.6 . . ? C22 C21 H21A 105.6 . . ? B2 C21 H21A 105.6 . . ? C23 C22 C21 112.7(2) . . ? C23 C22 H22A 109.1 . . ? C21 C22 H22A 109.1 . . ? C23 C22 H22B 109.1 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C22 110.5(2) . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23B 109.6 . . ? C22 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 111.0(2) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C24 C25 C26 111.2(2) . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C21 111.8(2) . . ? C25 C26 H26A 109.3 . . ? C21 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C21 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? C32 C31 C36 108.37(19) . . ? C32 C31 B1 115.90(19) . . ? C36 C31 B1 114.51(19) . . ? C32 C31 H31A 105.7 . . ? C36 C31 H31A 105.7 . . ? B1 C31 H31A 105.7 . . ? C33 C32 C31 112.6(2) . . ? C33 C32 H32A 109.1 . . ? C31 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C31 C32 H32B 109.1 . . ? H32A C32 H32B 107.8 . . ? C34 C33 C32 111.2(2) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C33 C34 C35 111.5(2) . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C36 111.5(2) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C31 112.6(2) . . ? C35 C36 H36A 109.1 . . ? C31 C36 H36A 109.1 . . ? C35 C36 H36B 109.1 . . ? C31 C36 H36B 109.1 . . ? H36A C36 H36B 107.8 . . ? C42 C41 C46 108.54(19) . . ? C42 C41 B1 117.50(19) . . ? C46 C41 B1 113.40(19) . . ? C42 C41 H41A 105.5 . . ? C46 C41 H41A 105.5 . . ? B1 C41 H41A 105.5 . . ? C41 C42 C43 111.8(2) . . ? C41 C42 H42A 109.3 . . ? C43 C42 H42A 109.3 . . ? C41 C42 H42B 109.3 . . ? C43 C42 H42B 109.3 . . ? H42A C42 H42B 107.9 . . ? C44 C43 C42 111.6(2) . . ? C44 C43 H43A 109.3 . . ? C42 C43 H43A 109.3 . . ? C44 C43 H43B 109.3 . . ? C42 C43 H43B 109.3 . . ? H43A C43 H43B 108.0 . . ? C45 C44 C43 111.2(2) . . ? C45 C44 H44A 109.4 . . ? C43 C44 H44A 109.4 . . ? C45 C44 H44B 109.4 . . ? C43 C44 H44B 109.4 . . ? H44A C44 H44B 108.0 . . ? C44 C45 C46 111.8(2) . . ? C44 C45 H45A 109.3 . . ? C46 C45 H45A 109.3 . . ? C44 C45 H45B 109.3 . . ? C46 C45 H45B 109.3 . . ? H45A C45 H45B 107.9 . . ? C45 C46 C41 111.4(2) . . ? C45 C46 H46A 109.3 . . ? C41 C46 H46A 109.3 . . ? C45 C46 H46B 109.3 . . ? C41 C46 H46B 109.3 . . ? H46A C46 H46B 108.0 . . ? C52 C51 C56 119.7(2) . . ? C52 C51 P1 124.62(19) . . ? C56 C51 P1 115.66(18) . . ? C53 C52 C51 119.4(2) . . ? C53 C52 H52 120.3 . . ? C51 C52 H52 120.3 . . ? C52 C53 C54 120.7(3) . . ? C52 C53 H53 119.7 . . ? C54 C53 H53 119.7 . . ? C55 C54 C53 120.0(2) . . ? C55 C54 H54 120.0 . . ? C53 C54 H54 120.0 . . ? C56 C55 C54 119.8(2) . . ? C56 C55 H55 120.1 . . ? C54 C55 H55 120.1 . . ? C55 C56 C51 120.4(2) . . ? C55 C56 H56 119.8 . . ? C51 C56 H56 119.8 . . ? C62 C61 C66 119.1(2) . . ? C62 C61 P1 117.55(17) . . ? C66 C61 P1 122.90(18) . . ? C63 C62 C61 120.4(2) . . ? C63 C62 H62 119.8 . . ? C61 C62 H62 119.8 . . ? C64 C63 C62 120.0(2) . . ? C64 C63 H63 120.0 . . ? C62 C63 H63 120.0 . . ? C65 C64 C63 120.1(2) . . ? C65 C64 H64 120.0 . . ? C63 C64 H64 120.0 . . ? C64 C65 C66 120.3(2) . . ? C64 C65 H65 119.8 . . ? C66 C65 H65 119.8 . . ? C65 C66 C61 120.2(2) . . ? C65 C66 H66 119.9 . . ? C61 C66 H66 119.9 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.424 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.049 data_rlm58_0m _database_code_depnum_ccdc_archive 'CCDC 918104' #TrackingRef 'CIFS-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C80 H132 B6 N6 O8' _chemical_formula_weight 1370.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3184(10) _cell_length_b 14.6317(15) _cell_length_c 15.0290(16) _cell_angle_alpha 69.271(5) _cell_angle_beta 88.761(5) _cell_angle_gamma 75.300(5) _cell_volume 2046.8(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9908 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 30.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9781 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26138 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7186 _reflns_number_gt 6302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+1.8384P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7186 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1608 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_restrained_S_all 1.210 _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 C6 C 1.0507(2) 0.20962(16) 0.43487(16) 0.0127(5) Uani 1 1 d . . . B1 B 1.0675(3) 0.3754(2) 0.33025(18) 0.0167(6) Uani 1 1 d . . . N1 N 1.02966(18) 0.30618(14) 0.27594(13) 0.0138(4) Uani 1 1 d . . . O2 O 1.06855(16) 0.29269(11) 0.43464(11) 0.0151(3) Uani 1 1 d . . . C5 C 1.0249(2) 0.21485(16) 0.33785(16) 0.0138(5) Uani 1 1 d . . . B2 B 0.9391(3) -0.10819(18) 0.38450(17) 0.0129(5) Uani 1 1 d . . . N2 N 1.00629(19) 0.31551(14) 0.18592(13) 0.0159(4) Uani 1 1 d . . . O4 O 1.05378(15) 0.13074(11) 0.50468(11) 0.0145(3) Uani 1 1 d . . . C4 C 0.9967(2) 0.16273(16) 0.28413(15) 0.0133(5) Uani 1 1 d . . . B3 B 0.9598(3) 0.17485(19) 0.11870(18) 0.0159(5) Uani 1 1 d . . . N3 N 0.98538(18) 0.22714(14) 0.19270(13) 0.0140(4) Uani 1 1 d . . . O1 O 0.95508(15) 0.07016(11) 0.20095(10) 0.0144(3) Uani 1 1 d . . . C3 C 0.9764(2) 0.06683(16) 0.28537(15) 0.0125(5) Uani 1 1 d . . . O3 O 0.98099(15) -0.00559(11) 0.36210(10) 0.0145(3) Uani 1 1 d . . . C11 C 0.9479(2) 0.47520(17) 0.31442(17) 0.0172(5) Uani 1 1 d . . . H11A H 0.9770 0.5124 0.3514 0.021 Uiso 1 1 calc R . . C12 C 0.9272(3) 0.54621(19) 0.20942(19) 0.0330(7) Uani 1 1 d . . . H12A H 1.0122 0.5640 0.1889 0.040 Uiso 1 1 calc R . . H12B H 0.9042 0.5103 0.1697 0.040 Uiso 1 1 calc R . . C13 C 0.8153(3) 0.6437(2) 0.1929(2) 0.0419(8) Uani 1 1 d . . . H13A H 0.8441 0.6846 0.2251 0.050 Uiso 1 1 calc R . . H13B H 0.8004 0.6841 0.1237 0.050 Uiso 1 1 calc R . . C14 C 0.6857(3) 0.6218(2) 0.2302(2) 0.0426(8) Uani 1 1 d . . . H14A H 0.6510 0.5881 0.1928 0.051 Uiso 1 1 calc R . . H14B H 0.6181 0.6862 0.2223 0.051 Uiso 1 1 calc R . . C15 C 0.7064(3) 0.5542(2) 0.3346(2) 0.0347(7) Uani 1 1 d . . . H15A H 0.6209 0.5383 0.3567 0.042 Uiso 1 1 calc R . . H15B H 0.7328 0.5906 0.3727 0.042 Uiso 1 1 calc R . . C16 C 0.8146(3) 0.4560(2) 0.3507(2) 0.0293(6) Uani 1 1 d . . . H16A H 0.7840 0.4168 0.3175 0.035 Uiso 1 1 calc R . . H16B H 0.8280 0.4149 0.4198 0.035 Uiso 1 1 calc R . . C21 C 1.2177(2) 0.38466(17) 0.31376(17) 0.0187(5) Uani 1 1 d . . . H21A H 1.2162 0.4368 0.2490 0.022 Uiso 1 1 calc R . . C22 C 1.3204(2) 0.28692(19) 0.31658(19) 0.0248(6) Uani 1 1 d . . . H22A H 1.3191 0.2322 0.3783 0.030 Uiso 1 1 calc R . . H22B H 1.2942 0.2662 0.2651 0.030 Uiso 1 1 calc R . . C23 C 1.4625(3) 0.2998(2) 0.3045(2) 0.0336(7) Uani 1 1 d . . . H23A H 1.5255 0.2346 0.3092 0.040 Uiso 1 1 calc R . . H23B H 1.4661 0.3501 0.2405 0.040 Uiso 1 1 calc R . . C24 C 1.5053(3) 0.3348(2) 0.3801(2) 0.0360(7) Uani 1 1 d . . . H24A H 1.5969 0.3441 0.3699 0.043 Uiso 1 1 calc R . . H24B H 1.5076 0.2824 0.4439 0.043 Uiso 1 1 calc R . . C25 C 1.4086(3) 0.4338(2) 0.3759(2) 0.0342(7) Uani 1 1 d . . . H25A H 1.4125 0.4876 0.3141 0.041 Uiso 1 1 calc R . . H25B H 1.4359 0.4539 0.4275 0.041 Uiso 1 1 calc R . . C26 C 1.2650(3) 0.42380(19) 0.38681(19) 0.0249(6) Uani 1 1 d . . . H26A H 1.2039 0.4907 0.3791 0.030 Uiso 1 1 calc R . . H26B H 1.2591 0.3767 0.4520 0.030 Uiso 1 1 calc R . . C31 C 0.7864(2) -0.08092(17) 0.34389(17) 0.0159(5) Uani 1 1 d . . . H31A H 0.7841 -0.0467 0.2731 0.019 Uiso 1 1 calc R . . C32 C 0.7350(2) -0.17541(19) 0.36168(19) 0.0240(6) Uani 1 1 d . . . H32A H 0.7960 -0.2214 0.3347 0.029 Uiso 1 1 calc R . . H32B H 0.7365 -0.2119 0.4313 0.029 Uiso 1 1 calc R . . C33 C 0.5929(3) -0.1486(2) 0.3171(2) 0.0324(7) Uani 1 1 d . . . H33A H 0.5927 -0.1179 0.2468 0.039 Uiso 1 1 calc R . . H33B H 0.5626 -0.2111 0.3324 0.039 Uiso 1 1 calc R . . C34 C 0.4964(3) -0.0751(2) 0.3534(2) 0.0372(7) Uani 1 1 d . . . H34A H 0.4884 -0.1089 0.4224 0.045 Uiso 1 1 calc R . . H34B H 0.4064 -0.0556 0.3199 0.045 Uiso 1 1 calc R . . C35 C 0.5437(3) 0.0195(2) 0.3376(2) 0.0336(7) Uani 1 1 d . . . H35A H 0.4825 0.0631 0.3668 0.040 Uiso 1 1 calc R . . H35B H 0.5398 0.0582 0.2683 0.040 Uiso 1 1 calc R . . C36 C 0.6867(2) -0.00657(19) 0.38073(19) 0.0247(6) Uani 1 1 d . . . H36A H 0.6879 -0.0371 0.4511 0.030 Uiso 1 1 calc R . . H36B H 0.7159 0.0564 0.3649 0.030 Uiso 1 1 calc R . . C41 C 1.0536(2) -0.19208(17) 0.36262(16) 0.0148(5) Uani 1 1 d . . . H41A H 1.0296 -0.2578 0.3933 0.018 Uiso 1 1 calc R . . C42 C 1.0592(2) -0.17463(18) 0.25526(17) 0.0208(5) Uani 1 1 d . . . H42A H 0.9698 -0.1702 0.2288 0.025 Uiso 1 1 calc R . . H42B H 1.0810 -0.1094 0.2215 0.025 Uiso 1 1 calc R . . C43 C 1.1636(3) -0.2594(2) 0.23748(18) 0.0267(6) Uani 1 1 d . . . H43A H 1.1672 -0.2438 0.1679 0.032 Uiso 1 1 calc R . . H43B H 1.1369 -0.3236 0.2656 0.032 Uiso 1 1 calc R . . C44 C 1.3022(3) -0.2727(2) 0.28092(19) 0.0281(6) Uani 1 1 d . . . H44A H 1.3670 -0.3303 0.2710 0.034 Uiso 1 1 calc R . . H44B H 1.3328 -0.2109 0.2486 0.034 Uiso 1 1 calc R . . C45 C 1.2987(2) -0.2920(2) 0.38712(19) 0.0264(6) Uani 1 1 d . . . H45A H 1.3885 -0.2969 0.4132 0.032 Uiso 1 1 calc R . . H45B H 1.2769 -0.3574 0.4202 0.032 Uiso 1 1 calc R . . C46 C 1.1946(2) -0.20741(19) 0.40586(18) 0.0209(5) Uani 1 1 d . . . H46A H 1.2219 -0.1435 0.3784 0.025 Uiso 1 1 calc R . . H46B H 1.1918 -0.2238 0.4756 0.025 Uiso 1 1 calc R . . C51 C 0.8142(2) 0.22544(17) 0.06263(16) 0.0175(5) Uani 1 1 d . . . H51A H 0.8074 0.1876 0.0197 0.021 Uiso 1 1 calc R . . C52 C 0.7956(3) 0.33675(19) -0.00228(18) 0.0265(6) Uani 1 1 d . . . H52A H 0.8064 0.3763 0.0372 0.032 Uiso 1 1 calc R . . H52B H 0.8665 0.3409 -0.0479 0.032 Uiso 1 1 calc R . . C53 C 0.6584(3) 0.3835(2) -0.0578(2) 0.0356(7) Uani 1 1 d . . . H53A H 0.6482 0.4566 -0.0935 0.043 Uiso 1 1 calc R . . H53B H 0.6527 0.3510 -0.1047 0.043 Uiso 1 1 calc R . . C54 C 0.5447(3) 0.3709(2) 0.0077(2) 0.0325(7) Uani 1 1 d . . . H54A H 0.5425 0.4113 0.0487 0.039 Uiso 1 1 calc R . . H54B H 0.4580 0.3970 -0.0313 0.039 Uiso 1 1 calc R . . C55 C 0.5616(3) 0.2609(2) 0.0699(2) 0.0339(7) Uani 1 1 d . . . H55A H 0.5539 0.2217 0.0293 0.041 Uiso 1 1 calc R . . H55B H 0.4892 0.2557 0.1143 0.041 Uiso 1 1 calc R . . C56 C 0.6975(2) 0.2163(2) 0.12675(19) 0.0266(6) Uani 1 1 d . . . H56A H 0.7071 0.1439 0.1650 0.032 Uiso 1 1 calc R . . H56B H 0.7015 0.2517 0.1714 0.032 Uiso 1 1 calc R . . C61 C 1.0919(2) 0.15362(17) 0.06377(16) 0.0167(5) Uani 1 1 d . . . H61A H 1.1002 0.2202 0.0175 0.020 Uiso 1 1 calc R . . C62 C 1.2223(2) 0.1033(2) 0.12989(18) 0.0242(6) Uani 1 1 d . . . H62A H 1.2388 0.1512 0.1584 0.029 Uiso 1 1 calc R . . H62B H 1.2105 0.0427 0.1825 0.029 Uiso 1 1 calc R . . C63 C 1.3444(3) 0.0718(2) 0.0782(2) 0.0323(7) Uani 1 1 d . . . H63A H 1.3628 0.1328 0.0301 0.039 Uiso 1 1 calc R . . H63B H 1.4240 0.0366 0.1245 0.039 Uiso 1 1 calc R . . C64 C 1.3210(3) 0.0020(2) 0.0292(2) 0.0301(6) Uani 1 1 d . . . H64A H 1.3053 -0.0602 0.0773 0.036 Uiso 1 1 calc R . . H64B H 1.4015 -0.0181 -0.0036 0.036 Uiso 1 1 calc R . . C65 C 1.1999(3) 0.0557(2) -0.04303(18) 0.0248(6) Uani 1 1 d . . . H65A H 1.1842 0.0096 -0.0741 0.030 Uiso 1 1 calc R . . H65B H 1.2175 0.1159 -0.0930 0.030 Uiso 1 1 calc R . . C66 C 1.0757(2) 0.08822(18) 0.00628(17) 0.0184(5) Uani 1 1 d . . . H66A H 1.0523 0.0268 0.0498 0.022 Uiso 1 1 calc R . . H66B H 0.9997 0.1267 -0.0426 0.022 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 C6 0.0131(11) 0.0134(11) 0.0127(11) -0.0059(9) 0.0026(9) -0.0038(9) B1 0.0271(15) 0.0160(13) 0.0105(13) -0.0056(11) 0.0014(10) -0.0107(11) N1 0.0178(10) 0.0133(10) 0.0114(10) -0.0046(8) 0.0020(7) -0.0058(8) O2 0.0230(9) 0.0126(8) 0.0133(8) -0.0055(7) 0.0026(6) -0.0097(6) C5 0.0145(11) 0.0117(11) 0.0144(12) -0.0038(9) 0.0016(9) -0.0033(9) B2 0.0217(14) 0.0116(12) 0.0081(12) -0.0036(10) 0.0016(10) -0.0089(10) N2 0.0236(11) 0.0135(10) 0.0119(10) -0.0053(8) 0.0019(8) -0.0062(8) O4 0.0209(8) 0.0124(8) 0.0116(8) -0.0048(7) 0.0027(6) -0.0063(6) C4 0.0132(11) 0.0140(11) 0.0121(11) -0.0042(9) 0.0014(8) -0.0032(9) B3 0.0268(15) 0.0107(13) 0.0129(13) -0.0052(10) 0.0000(11) -0.0079(11) N3 0.0191(10) 0.0122(9) 0.0123(10) -0.0053(8) 0.0015(8) -0.0056(8) O1 0.0193(8) 0.0140(8) 0.0114(8) -0.0059(6) 0.0003(6) -0.0053(6) C3 0.0130(11) 0.0124(11) 0.0141(12) -0.0067(9) 0.0011(9) -0.0043(9) O3 0.0209(8) 0.0127(8) 0.0112(8) -0.0032(7) 0.0015(6) -0.0081(6) C11 0.0202(12) 0.0149(12) 0.0189(12) -0.0072(10) 0.0028(9) -0.0071(9) C12 0.0450(17) 0.0179(14) 0.0257(15) -0.0022(11) 0.0086(13) 0.0008(12) C13 0.053(2) 0.0215(15) 0.0317(17) 0.0021(12) 0.0075(14) 0.0066(13) C14 0.0353(17) 0.0353(17) 0.0482(19) -0.0171(15) -0.0084(14) 0.0101(13) C15 0.0232(14) 0.0297(15) 0.0472(18) -0.0106(13) 0.0085(13) -0.0055(12) C16 0.0249(14) 0.0225(14) 0.0380(16) -0.0065(12) 0.0080(12) -0.0087(11) C21 0.0234(13) 0.0162(12) 0.0161(12) -0.0036(10) 0.0007(10) -0.0079(10) C22 0.0230(13) 0.0250(14) 0.0307(15) -0.0145(11) 0.0053(11) -0.0077(11) C23 0.0233(14) 0.0330(16) 0.0429(18) -0.0116(13) 0.0090(12) -0.0080(12) C24 0.0230(14) 0.0354(16) 0.0494(19) -0.0097(14) -0.0006(13) -0.0148(12) C25 0.0308(15) 0.0321(16) 0.0454(18) -0.0137(14) -0.0019(13) -0.0179(12) C26 0.0292(14) 0.0214(13) 0.0298(15) -0.0128(11) 0.0010(11) -0.0111(11) C31 0.0174(12) 0.0147(11) 0.0159(12) -0.0056(9) 0.0009(9) -0.0047(9) C32 0.0221(13) 0.0222(13) 0.0309(15) -0.0098(11) -0.0018(11) -0.0105(10) C33 0.0260(15) 0.0273(15) 0.0441(18) -0.0095(13) -0.0089(12) -0.0114(12) C34 0.0183(14) 0.0369(17) 0.0483(19) -0.0030(14) -0.0017(12) -0.0108(12) C35 0.0203(14) 0.0290(15) 0.0479(18) -0.0119(13) 0.0031(12) -0.0030(11) C36 0.0210(13) 0.0233(13) 0.0319(15) -0.0132(11) 0.0032(11) -0.0049(10) C41 0.0197(12) 0.0116(11) 0.0134(12) -0.0047(9) 0.0002(9) -0.0046(9) C42 0.0240(13) 0.0207(13) 0.0164(13) -0.0093(10) -0.0014(10) 0.0002(10) C43 0.0339(15) 0.0253(14) 0.0184(13) -0.0125(11) 0.0009(11) 0.0033(11) C44 0.0247(14) 0.0284(14) 0.0265(14) -0.0104(12) 0.0086(11) 0.0014(11) C45 0.0176(13) 0.0311(15) 0.0272(14) -0.0111(12) -0.0014(10) 0.0001(11) C46 0.0187(12) 0.0261(13) 0.0203(13) -0.0103(11) 0.0010(10) -0.0072(10) C51 0.0213(12) 0.0159(12) 0.0161(12) -0.0078(10) 0.0013(10) -0.0033(10) C52 0.0310(14) 0.0206(13) 0.0207(13) -0.0019(11) 0.0031(11) -0.0026(11) C53 0.0388(17) 0.0299(15) 0.0244(15) -0.0034(12) -0.0024(12) 0.0059(12) C54 0.0266(14) 0.0321(15) 0.0309(16) -0.0114(13) -0.0066(12) 0.0069(12) C55 0.0226(14) 0.0356(16) 0.0435(18) -0.0159(14) 0.0012(12) -0.0049(12) C56 0.0222(13) 0.0255(14) 0.0249(14) -0.0021(11) 0.0036(11) -0.0040(11) C61 0.0228(12) 0.0170(12) 0.0128(12) -0.0051(9) 0.0025(9) -0.0097(10) C62 0.0218(13) 0.0332(15) 0.0216(13) -0.0136(11) 0.0015(10) -0.0086(11) C63 0.0204(14) 0.0489(18) 0.0344(16) -0.0235(14) 0.0036(11) -0.0085(12) C64 0.0208(13) 0.0370(16) 0.0353(16) -0.0191(13) 0.0078(11) -0.0041(11) C65 0.0278(14) 0.0290(14) 0.0250(14) -0.0170(12) 0.0073(11) -0.0101(11) C66 0.0190(12) 0.0227(13) 0.0160(12) -0.0102(10) 0.0008(9) -0.0054(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 C6 O4 1.249(3) . ? C6 O2 1.274(3) . ? C6 C5 1.459(3) . ? B1 C21 1.597(4) . ? B1 C11 1.601(4) . ? B1 O2 1.605(3) . ? B1 N1 1.625(3) . ? N1 N2 1.332(3) . ? N1 C5 1.343(3) . ? C5 C4 1.370(3) . ? B2 O4 1.579(3) 2_756 ? B2 O3 1.587(3) . ? B2 C41 1.595(3) . ? B2 C31 1.601(3) . ? N2 N3 1.333(3) . ? O4 B2 1.579(3) 2_756 ? C4 N3 1.351(3) . ? C4 C3 1.464(3) . ? B3 C61 1.598(3) . ? B3 C51 1.602(3) . ? B3 O1 1.604(3) . ? B3 N3 1.615(3) . ? O1 C3 1.274(3) . ? C3 O3 1.252(3) . ? C11 C16 1.525(3) . ? C11 C12 1.535(3) . ? C11 H11A 1.0000 . ? C12 C13 1.535(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.505(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.515(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C21 C22 1.536(3) . ? C21 C26 1.543(3) . ? C21 H21A 1.0000 . ? C22 C23 1.524(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.514(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.518(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.525(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C31 C32 1.539(3) . ? C31 C36 1.543(3) . ? C31 H31A 1.0000 . ? C32 C33 1.522(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.514(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.523(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.524(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C41 C46 1.536(3) . ? C41 C42 1.544(3) . ? C41 H41A 1.0000 . ? C42 C43 1.522(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.523(4) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.520(4) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.525(3) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C51 C56 1.529(3) . ? C51 C52 1.538(3) . ? C51 H51A 1.0000 . ? C52 C53 1.525(4) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.520(4) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.515(4) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.522(4) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C61 C66 1.537(3) . ? C61 C62 1.542(3) . ? C61 H61A 1.0000 . ? C62 C63 1.523(4) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C63 C64 1.520(4) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 C65 1.521(4) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 C66 1.522(3) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? 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 C6 O2 128.4(2) . . ? O4 C6 C5 120.72(19) . . ? O2 C6 C5 110.88(19) . . ? C21 B1 C11 119.6(2) . . ? C21 B1 O2 107.66(19) . . ? C11 B1 O2 110.51(19) . . ? C21 B1 N1 110.94(19) . . ? C11 B1 N1 111.27(19) . . ? O2 B1 N1 93.74(15) . . ? N2 N1 C5 111.92(18) . . ? N2 N1 B1 136.47(18) . . ? C5 N1 B1 111.57(18) . . ? C6 O2 B1 114.39(17) . . ? N1 C5 C4 106.28(19) . . ? N1 C5 C6 109.23(19) . . ? C4 C5 C6 144.5(2) . . ? O4 B2 O3 92.12(14) 2_756 . ? O4 B2 C41 109.02(18) 2_756 . ? O3 B2 C41 111.92(18) . . ? O4 B2 C31 110.28(18) 2_756 . ? O3 B2 C31 108.34(18) . . ? C41 B2 C31 121.29(19) . . ? N1 N2 N3 104.32(17) . . ? C6 O4 B2 131.50(17) . 2_756 ? N3 C4 C5 105.35(19) . . ? N3 C4 C3 108.80(18) . . ? C5 C4 C3 145.8(2) . . ? C61 B3 C51 121.3(2) . . ? C61 B3 O1 107.92(18) . . ? C51 B3 O1 107.81(18) . . ? C61 B3 N3 109.71(18) . . ? C51 B3 N3 112.43(19) . . ? O1 B3 N3 94.08(16) . . ? N2 N3 C4 112.12(18) . . ? N2 N3 B3 135.94(18) . . ? C4 N3 B3 111.77(17) . . ? C3 O1 B3 114.35(17) . . ? O3 C3 O1 127.8(2) . . ? O3 C3 C4 121.33(19) . . ? O1 C3 C4 110.91(19) . . ? C3 O3 B2 131.14(17) . . ? C16 C11 C12 110.1(2) . . ? C16 C11 B1 115.04(19) . . ? C12 C11 B1 111.30(19) . . ? C16 C11 H11A 106.6 . . ? C12 C11 H11A 106.6 . . ? B1 C11 H11A 106.6 . . ? C13 C12 C11 112.3(2) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 111.9(2) . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 110.9(2) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.3(2) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C11 112.1(2) . . ? C15 C16 H16A 109.2 . . ? C11 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C11 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C22 C21 C26 109.7(2) . . ? C22 C21 B1 114.97(19) . . ? C26 C21 B1 109.98(19) . . ? C22 C21 H21A 107.3 . . ? C26 C21 H21A 107.3 . . ? B1 C21 H21A 107.3 . . ? C23 C22 C21 112.3(2) . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22B 109.2 . . ? C21 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C22 111.0(2) . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C25 110.6(2) . . ? C23 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C24 C25 C26 111.1(2) . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C21 113.0(2) . . ? C25 C26 H26A 109.0 . . ? C21 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C21 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C32 C31 C36 109.07(19) . . ? C32 C31 B2 112.78(19) . . ? C36 C31 B2 114.27(19) . . ? C32 C31 H31A 106.7 . . ? C36 C31 H31A 106.7 . . ? B2 C31 H31A 106.7 . . ? C33 C32 C31 112.1(2) . . ? C33 C32 H32A 109.2 . . ? C31 C32 H32A 109.2 . . ? C33 C32 H32B 109.2 . . ? C31 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C34 C33 C32 111.2(2) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C33 C34 C35 111.5(2) . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C36 111.7(2) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 107.9 . . ? C35 C36 C31 112.2(2) . . ? C35 C36 H36A 109.2 . . ? C31 C36 H36A 109.2 . . ? C35 C36 H36B 109.2 . . ? C31 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? C46 C41 C42 109.56(19) . . ? C46 C41 B2 114.35(18) . . ? C42 C41 B2 113.28(18) . . ? C46 C41 H41A 106.3 . . ? C42 C41 H41A 106.3 . . ? B2 C41 H41A 106.3 . . ? C43 C42 C41 111.85(19) . . ? C43 C42 H42A 109.2 . . ? C41 C42 H42A 109.2 . . ? C43 C42 H42B 109.2 . . ? C41 C42 H42B 109.2 . . ? H42A C42 H42B 107.9 . . ? C42 C43 C44 111.3(2) . . ? C42 C43 H43A 109.4 . . ? C44 C43 H43A 109.4 . . ? C42 C43 H43B 109.4 . . ? C44 C43 H43B 109.4 . . ? H43A C43 H43B 108.0 . . ? C45 C44 C43 110.7(2) . . ? C45 C44 H44A 109.5 . . ? C43 C44 H44A 109.5 . . ? C45 C44 H44B 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 108.1 . . ? C44 C45 C46 111.2(2) . . ? C44 C45 H45A 109.4 . . ? C46 C45 H45A 109.4 . . ? C44 C45 H45B 109.4 . . ? C46 C45 H45B 109.4 . . ? H45A C45 H45B 108.0 . . ? C45 C46 C41 112.2(2) . . ? C45 C46 H46A 109.2 . . ? C41 C46 H46A 109.2 . . ? C45 C46 H46B 109.2 . . ? C41 C46 H46B 109.2 . . ? H46A C46 H46B 107.9 . . ? C56 C51 C52 109.8(2) . . ? C56 C51 B3 114.3(2) . . ? C52 C51 B3 112.76(19) . . ? C56 C51 H51A 106.5 . . ? C52 C51 H51A 106.5 . . ? B3 C51 H51A 106.5 . . ? C53 C52 C51 112.5(2) . . ? C53 C52 H52A 109.1 . . ? C51 C52 H52A 109.1 . . ? C53 C52 H52B 109.1 . . ? C51 C52 H52B 109.1 . . ? H52A C52 H52B 107.8 . . ? C54 C53 C52 111.8(2) . . ? C54 C53 H53A 109.3 . . ? C52 C53 H53A 109.3 . . ? C54 C53 H53B 109.3 . . ? C52 C53 H53B 109.3 . . ? H53A C53 H53B 107.9 . . ? C55 C54 C53 111.4(2) . . ? C55 C54 H54A 109.3 . . ? C53 C54 H54A 109.3 . . ? C55 C54 H54B 109.3 . . ? C53 C54 H54B 109.3 . . ? H54A C54 H54B 108.0 . . ? C54 C55 C56 110.9(2) . . ? C54 C55 H55A 109.5 . . ? C56 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? C56 C55 H55B 109.5 . . ? H55A C55 H55B 108.0 . . ? C55 C56 C51 112.3(2) . . ? C55 C56 H56A 109.1 . . ? C51 C56 H56A 109.1 . . ? C55 C56 H56B 109.1 . . ? C51 C56 H56B 109.1 . . ? H56A C56 H56B 107.9 . . ? C66 C61 C62 110.09(19) . . ? C66 C61 B3 109.43(18) . . ? C62 C61 B3 113.76(19) . . ? C66 C61 H61A 107.8 . . ? C62 C61 H61A 107.8 . . ? B3 C61 H61A 107.8 . . ? C63 C62 C61 112.9(2) . . ? C63 C62 H62A 109.0 . . ? C61 C62 H62A 109.0 . . ? C63 C62 H62B 109.0 . . ? C61 C62 H62B 109.0 . . ? H62A C62 H62B 107.8 . . ? C64 C63 C62 110.9(2) . . ? C64 C63 H63A 109.5 . . ? C62 C63 H63A 109.5 . . ? C64 C63 H63B 109.5 . . ? C62 C63 H63B 109.5 . . ? H63A C63 H63B 108.0 . . ? C63 C64 C65 109.9(2) . . ? C63 C64 H64A 109.7 . . ? C65 C64 H64A 109.7 . . ? C63 C64 H64B 109.7 . . ? C65 C64 H64B 109.7 . . ? H64A C64 H64B 108.2 . . ? C64 C65 C66 110.2(2) . . ? C64 C65 H65A 109.6 . . ? C66 C65 H65A 109.6 . . ? C64 C65 H65B 109.6 . . ? C66 C65 H65B 109.6 . . ? H65A C65 H65B 108.1 . . ? C65 C66 C61 114.39(19) . . ? C65 C66 H66A 108.7 . . ? C61 C66 H66A 108.7 . . ? C65 C66 H66B 108.7 . . ? C61 C66 H66B 108.7 . . ? H66A C66 H66B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.290 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.052 #===end