# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Hans-Georg Stammler ; _publ_contact_author_phone '49 521 1066165' _publ_contact_author_fax '49 521 1066146' _publ_contact_author_email georg.stammler@uni-bielefeld.de _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for deposition. To: dalton@rsc.org Subject: Depositing Crystal Structure Data Dear Madam or Sir, please find enclosed the crystallographic data of compound2 'C28 H28 B N2 P' compound3 'C28 H29 B N2 O1.50 P' compound4 'C28 H28 B N2 P S' compound5 'C28 H28 B N2 P Se' compound6 'C33 H40 Au B Cl N2 P' compound7 'C30 H34 B N2 O4 P S' compound8 'C26 H26 B N2 P S' compound9 'C26 H26 B N2 P S2' compound11 'C28 H32 B N2 O4 P S2' for deposition with the CCDC. With kind regards Beate Neumann ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Syntheses of Rod-Shaped Fluorescent 1,3,2-Benzodiazaboroles with Phosphonium, and Phosphane Chalcogenide Acceptor Functions ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address L.Weber ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; H.Kuhtz ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; J.Kahlert ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; L.Bohling ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; A.Brockhinke ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; ; A.Chrostowska ; ; Universit\'e de Pau et des Pays de l\'Adour UMR5254 - IPREM Equipe Chimie-Physique H\'elioparc - 2 Av. du Pr\'esident Angot BP 1155 64013 Pau Cedex 09 FRANCE ; A.Dargelos ; Universit\'e de Pau et des Pays de l\'Adour UMR5254 - IPREM Equipe Chimie-Physique H\'elioparc - 2 Av. du Pr\'esident Angot BP 1155 64013 Pau Cedex 09 FRANCE ; H.-G.Stammler ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; B.Neumann ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; _publ_contact_author_name 'Dr. Hans-Georg Stammler' #============================================================================== data_compound2 _database_code_depnum_ccdc_archive 'CCDC 873268' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 B N2 P' _chemical_formula_sum 'C28 H28 B N2 P' _chemical_formula_weight 434.30 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9777(2) _cell_length_b 10.8375(2) _cell_length_c 12.8536(2) _cell_angle_alpha 103.8797(11) _cell_angle_beta 101.0244(11) _cell_angle_gamma 112.4832(10) _cell_volume 1183.10(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24946 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36873 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5392 _reflns_number_gt 4571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.3926P] 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 5392 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.21237(4) 0.35112(3) 0.11246(3) 0.02082(9) Uani 1 1 d . . . N1 N 0.65748(11) 1.10283(11) 0.40358(8) 0.0199(2) Uani 1 1 d . . . N2 N 0.44890(11) 1.10725(11) 0.29558(9) 0.0200(2) Uani 1 1 d . . . B1 B 0.51004(16) 1.01393(15) 0.32080(11) 0.0191(3) Uani 1 1 d . . . C1 C 0.68557(14) 1.24469(13) 0.42566(10) 0.0215(3) Uani 1 1 d . . . C2 C 0.55695(14) 1.24751(13) 0.36038(10) 0.0210(3) Uani 1 1 d . . . C3 C 0.55161(16) 1.37504(14) 0.36612(11) 0.0256(3) Uani 1 1 d . . . H3 H 0.4655 1.3769 0.3211 0.031 Uiso 1 1 calc R . . C4 C 0.67720(16) 1.50039(14) 0.44037(12) 0.0291(3) Uani 1 1 d . . . H4 H 0.6759 1.5891 0.4468 0.035 Uiso 1 1 calc R . . C5 C 0.80406(16) 1.49807(14) 0.50505(12) 0.0296(3) Uani 1 1 d . . . H5 H 0.8880 1.5852 0.5548 0.036 Uiso 1 1 calc R . . C6 C 0.81047(15) 1.37025(14) 0.49835(11) 0.0257(3) Uani 1 1 d . . . H6 H 0.8979 1.3691 0.5423 0.031 Uiso 1 1 calc R . . C7 C 0.77450(15) 1.06441(14) 0.45143(11) 0.0252(3) Uani 1 1 d . . . H7A H 0.7249 0.9639 0.4468 0.030 Uiso 1 1 calc R . . H7B H 0.8256 1.1242 0.5322 0.030 Uiso 1 1 calc R . . C8 C 0.89392(16) 1.08330(15) 0.39117(13) 0.0310(3) Uani 1 1 d . . . H8A H 0.8456 1.0175 0.3129 0.047 Uiso 1 1 calc R . . H8B H 0.9737 1.0632 0.4298 0.047 Uiso 1 1 calc R . . H8C H 0.9396 1.1814 0.3919 0.047 Uiso 1 1 calc R . . C9 C 0.29797(14) 1.07433(14) 0.22484(11) 0.0230(3) Uani 1 1 d . . . H9A H 0.2478 0.9738 0.1742 0.028 Uiso 1 1 calc R . . H9B H 0.3100 1.1347 0.1770 0.028 Uiso 1 1 calc R . . C10 C 0.19574(15) 1.09810(15) 0.29325(12) 0.0286(3) Uani 1 1 d . . . H10A H 0.1849 1.0400 0.3418 0.043 Uiso 1 1 calc R . . H10B H 0.0949 1.0708 0.2419 0.043 Uiso 1 1 calc R . . H10C H 0.2416 1.1988 0.3401 0.043 Uiso 1 1 calc R . . C11 C 0.43253(13) 0.84771(13) 0.26714(10) 0.0184(2) Uani 1 1 d . . . C12 C 0.37323(14) 0.77838(13) 0.14950(10) 0.0201(2) Uani 1 1 d . . . H12 H 0.3803 0.8339 0.1018 0.024 Uiso 1 1 calc R . . C13 C 0.30455(14) 0.63108(13) 0.10085(10) 0.0204(2) Uani 1 1 d . . . H13 H 0.2646 0.5877 0.0210 0.024 Uiso 1 1 calc R . . C14 C 0.29368(13) 0.54599(13) 0.16843(10) 0.0192(2) Uani 1 1 d . . . C15 C 0.35479(14) 0.61377(13) 0.28595(10) 0.0206(2) Uani 1 1 d . . . H15 H 0.3506 0.5582 0.3334 0.025 Uiso 1 1 calc R . . C16 C 0.42129(14) 0.76090(13) 0.33387(10) 0.0199(2) Uani 1 1 d . . . H16 H 0.4602 0.8041 0.4138 0.024 Uiso 1 1 calc R . . C17 C 0.17474(14) 0.31743(12) -0.03935(11) 0.0208(2) Uani 1 1 d . . . C18 C 0.29225(15) 0.31725(14) -0.08382(12) 0.0279(3) Uani 1 1 d . . . H18 H 0.3847 0.3284 -0.0362 0.033 Uiso 1 1 calc R . . C19 C 0.27513(16) 0.30089(15) -0.19682(12) 0.0324(3) Uani 1 1 d . . . H19 H 0.3565 0.3031 -0.2257 0.039 Uiso 1 1 calc R . . C20 C 0.13899(16) 0.28123(14) -0.26769(11) 0.0292(3) Uani 1 1 d . . . H20 H 0.1270 0.2696 -0.3451 0.035 Uiso 1 1 calc R . . C21 C 0.02059(15) 0.27867(13) -0.22505(11) 0.0252(3) Uani 1 1 d . . . H21 H -0.0731 0.2638 -0.2736 0.030 Uiso 1 1 calc R . . C22 C 0.03882(14) 0.29787(13) -0.11137(11) 0.0220(3) Uani 1 1 d . . . H22 H -0.0421 0.2977 -0.0825 0.026 Uiso 1 1 calc R . . C23 C 0.01938(14) 0.29164(13) 0.12503(10) 0.0210(3) Uani 1 1 d . . . C24 C -0.07866(16) 0.14531(14) 0.07977(11) 0.0266(3) Uani 1 1 d . . . H24 H -0.0447 0.0821 0.0419 0.032 Uiso 1 1 calc R . . C25 C -0.22476(16) 0.09104(15) 0.08934(11) 0.0296(3) Uani 1 1 d . . . H25 H -0.2901 -0.0084 0.0573 0.035 Uiso 1 1 calc R . . C26 C -0.27497(16) 0.18209(15) 0.14569(11) 0.0290(3) Uani 1 1 d . . . H26 H -0.3748 0.1453 0.1523 0.035 Uiso 1 1 calc R . . C27 C -0.17907(16) 0.32683(15) 0.19228(12) 0.0296(3) Uani 1 1 d . . . H27 H -0.2128 0.3893 0.2317 0.036 Uiso 1 1 calc R . . C28 C -0.03327(15) 0.38120(14) 0.18158(11) 0.0250(3) Uani 1 1 d . . . H28 H 0.0312 0.4808 0.2133 0.030 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 0.02157(17) 0.01854(16) 0.02218(17) 0.00589(13) 0.00554(13) 0.01017(13) N1 0.0193(5) 0.0203(5) 0.0189(5) 0.0057(4) 0.0065(4) 0.0081(4) N2 0.0189(5) 0.0175(5) 0.0216(5) 0.0052(4) 0.0067(4) 0.0069(4) B1 0.0197(7) 0.0220(7) 0.0177(6) 0.0081(5) 0.0097(5) 0.0090(6) C1 0.0230(6) 0.0208(6) 0.0205(6) 0.0062(5) 0.0118(5) 0.0080(5) C2 0.0223(6) 0.0196(6) 0.0202(6) 0.0058(5) 0.0109(5) 0.0072(5) C3 0.0282(7) 0.0229(6) 0.0293(7) 0.0104(5) 0.0141(6) 0.0118(6) C4 0.0364(8) 0.0192(6) 0.0338(7) 0.0085(6) 0.0200(6) 0.0106(6) C5 0.0285(7) 0.0209(6) 0.0275(7) 0.0010(5) 0.0139(6) 0.0013(5) C6 0.0222(6) 0.0255(7) 0.0222(6) 0.0039(5) 0.0093(5) 0.0052(5) C7 0.0225(6) 0.0269(7) 0.0227(6) 0.0074(5) 0.0031(5) 0.0104(5) C8 0.0251(7) 0.0280(7) 0.0414(8) 0.0105(6) 0.0120(6) 0.0136(6) C9 0.0214(6) 0.0221(6) 0.0254(6) 0.0081(5) 0.0051(5) 0.0107(5) C10 0.0241(7) 0.0288(7) 0.0364(8) 0.0127(6) 0.0116(6) 0.0136(6) C11 0.0155(6) 0.0206(6) 0.0208(6) 0.0071(5) 0.0072(5) 0.0091(5) C12 0.0202(6) 0.0215(6) 0.0201(6) 0.0087(5) 0.0065(5) 0.0098(5) C13 0.0201(6) 0.0222(6) 0.0176(6) 0.0053(5) 0.0042(5) 0.0100(5) C14 0.0170(6) 0.0191(6) 0.0216(6) 0.0060(5) 0.0061(5) 0.0086(5) C15 0.0211(6) 0.0224(6) 0.0212(6) 0.0094(5) 0.0085(5) 0.0104(5) C16 0.0200(6) 0.0225(6) 0.0176(6) 0.0058(5) 0.0078(5) 0.0095(5) C17 0.0224(6) 0.0151(5) 0.0233(6) 0.0037(5) 0.0077(5) 0.0082(5) C18 0.0229(7) 0.0271(7) 0.0305(7) 0.0044(6) 0.0092(6) 0.0110(6) C19 0.0285(7) 0.0335(8) 0.0332(8) 0.0052(6) 0.0175(6) 0.0119(6) C20 0.0344(8) 0.0243(7) 0.0226(7) 0.0038(5) 0.0119(6) 0.0081(6) C21 0.0260(7) 0.0206(6) 0.0237(6) 0.0045(5) 0.0054(5) 0.0082(5) C22 0.0214(6) 0.0195(6) 0.0243(6) 0.0054(5) 0.0088(5) 0.0088(5) C23 0.0239(6) 0.0216(6) 0.0187(6) 0.0087(5) 0.0066(5) 0.0102(5) C24 0.0323(7) 0.0212(6) 0.0256(7) 0.0069(5) 0.0110(6) 0.0112(6) C25 0.0329(7) 0.0232(7) 0.0261(7) 0.0083(5) 0.0098(6) 0.0060(6) C26 0.0269(7) 0.0341(7) 0.0253(7) 0.0132(6) 0.0130(6) 0.0090(6) C27 0.0317(7) 0.0315(7) 0.0286(7) 0.0096(6) 0.0148(6) 0.0152(6) C28 0.0271(7) 0.0207(6) 0.0262(7) 0.0071(5) 0.0091(5) 0.0099(5) _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 C17 1.8316(13) . ? P1 C23 1.8356(13) . ? P1 C14 1.8366(12) . ? N1 C1 1.3976(16) . ? N1 B1 1.4318(17) . ? N1 C7 1.4612(16) . ? N2 C2 1.4008(16) . ? N2 B1 1.4330(17) . ? N2 C9 1.4600(16) . ? B1 C11 1.5663(18) . ? C1 C6 1.3876(18) . ? C1 C2 1.4080(18) . ? C2 C3 1.3883(18) . ? C3 C4 1.3947(19) . ? C3 H3 0.9500 . ? C4 C5 1.388(2) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5179(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5217(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.4049(17) . ? C11 C16 1.4059(17) . ? C12 C13 1.3890(17) . ? C12 H12 0.9500 . ? C13 C14 1.4002(17) . ? C13 H13 0.9500 . ? C14 C15 1.4022(17) . ? C15 C16 1.3876(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.3954(18) . ? C17 C18 1.3997(18) . ? C18 C19 1.389(2) . ? C18 H18 0.9500 . ? C19 C20 1.390(2) . ? C19 H19 0.9500 . ? C20 C21 1.3880(19) . ? C20 H20 0.9500 . ? C21 C22 1.3910(18) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.3942(17) . ? C23 C24 1.4012(18) . ? C24 C25 1.3905(19) . ? C24 H24 0.9500 . ? C25 C26 1.387(2) . ? C25 H25 0.9500 . ? C26 C27 1.385(2) . ? C26 H26 0.9500 . ? C27 C28 1.3936(19) . ? C27 H27 0.9500 . ? C28 H28 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 C17 P1 C23 102.24(6) . . ? C17 P1 C14 101.26(5) . . ? C23 P1 C14 103.43(5) . . ? C1 N1 B1 108.43(10) . . ? C1 N1 C7 121.76(10) . . ? B1 N1 C7 129.42(11) . . ? C2 N2 B1 108.22(10) . . ? C2 N2 C9 121.56(10) . . ? B1 N2 C9 130.01(10) . . ? N1 B1 N2 106.42(11) . . ? N1 B1 C11 126.64(11) . . ? N2 B1 C11 126.94(11) . . ? C6 C1 N1 131.03(12) . . ? C6 C1 C2 120.52(12) . . ? N1 C1 C2 108.43(11) . . ? C3 C2 N2 130.24(12) . . ? C3 C2 C1 121.27(12) . . ? N2 C2 C1 108.48(11) . . ? C2 C3 C4 117.64(13) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.26(12) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.19(12) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.11(13) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? N1 C7 C8 112.62(11) . . ? N1 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? N1 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 112.80(11) . . ? N2 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 116.81(11) . . ? C12 C11 B1 121.35(11) . . ? C16 C11 B1 121.83(11) . . ? C13 C12 C11 121.91(11) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 120.62(11) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C15 118.12(11) . . ? C13 C14 P1 123.99(9) . . ? C15 C14 P1 117.83(9) . . ? C16 C15 C14 120.86(11) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C11 121.66(11) . . ? C15 C16 H16 119.2 . . ? C11 C16 H16 119.2 . . ? C22 C17 C18 118.66(12) . . ? C22 C17 P1 123.76(9) . . ? C18 C17 P1 117.53(10) . . ? C19 C18 C17 120.67(13) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 120.06(12) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 119.80(12) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.15(13) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 120.63(12) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? C28 C23 C24 117.90(12) . . ? C28 C23 P1 124.44(10) . . ? C24 C23 P1 117.57(10) . . ? C25 C24 C23 121.17(12) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C26 C25 C24 119.97(13) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 119.73(13) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C28 120.23(13) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 120.99(12) . . ? C27 C28 H28 119.5 . . ? C23 C28 H28 119.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.271 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.046 #============================================================================== data_compound3 _database_code_depnum_ccdc_archive 'CCDC 873269' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 B N2 O P, 0.5 H2 O' _chemical_formula_sum 'C28 H29 B N2 O1.50 P' _chemical_formula_weight 459.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0888(2) _cell_length_b 9.2706(2) _cell_length_c 32.2486(6) _cell_angle_alpha 92.2206(11) _cell_angle_beta 94.3510(10) _cell_angle_gamma 112.3154(11) _cell_volume 2499.75(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 41406 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9606 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38832 _diffrn_reflns_av_R_equivalents 0.061 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11204 _reflns_number_gt 7626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1101P)^2^+2.3478P] 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 11204 _refine_ls_number_parameters 616 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.2264 _refine_ls_wR_factor_gt 0.2066 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 -0.13603(9) 0.29453(9) 0.33544(2) 0.0322(2) Uani 1 1 d . . . P2 P 0.27899(11) 0.61190(10) 0.17786(2) 0.0382(2) Uani 1 1 d . . . O1 O -0.0730(3) 0.4604(3) 0.32466(7) 0.0419(5) Uani 1 1 d . . . O2 O 0.1248(3) 0.5427(3) 0.19682(7) 0.0533(6) Uani 1 1 d . . . N1 N 0.1626(3) 0.2820(3) 0.54819(8) 0.0364(6) Uani 1 1 d . . . N2 N 0.3430(3) 0.2262(3) 0.51104(7) 0.0340(6) Uani 1 1 d . . . N3 N 0.2769(3) 0.1660(3) -0.00361(8) 0.0355(6) Uani 1 1 d . . . N4 N 0.1917(3) 0.3355(3) -0.03900(8) 0.0362(6) Uani 1 1 d . . . B1 B 0.1981(4) 0.2550(4) 0.50698(11) 0.0344(7) Uani 1 1 d . . . B2 B 0.2364(4) 0.3005(4) 0.00194(11) 0.0344(7) Uani 1 1 d . . . C1 C 0.2825(4) 0.2700(4) 0.57638(9) 0.0346(6) Uani 1 1 d . . . C2 C 0.3909(4) 0.2345(4) 0.55385(9) 0.0345(6) Uani 1 1 d . . . C3 C 0.5202(4) 0.2126(4) 0.57403(10) 0.0419(7) Uani 1 1 d . . . H3 H 0.5924 0.1854 0.5588 0.050 Uiso 1 1 calc R . . C4 C 0.5409(4) 0.2318(5) 0.61741(11) 0.0486(9) Uani 1 1 d . . . H4 H 0.6288 0.2177 0.6319 0.058 Uiso 1 1 calc R . . C5 C 0.4358(4) 0.2708(5) 0.63963(10) 0.0484(9) Uani 1 1 d . . . H5 H 0.4540 0.2852 0.6692 0.058 Uiso 1 1 calc R . . C6 C 0.3040(4) 0.2896(4) 0.61970(10) 0.0418(7) Uani 1 1 d . . . H6 H 0.2310 0.3150 0.6351 0.050 Uiso 1 1 calc R . . C7 C 0.0294(4) 0.3127(5) 0.56286(11) 0.0512(9) Uani 1 1 d . . . H7A H -0.0270 0.3426 0.5394 0.061 Uiso 1 1 calc R . . H7B H 0.0705 0.4015 0.5843 0.061 Uiso 1 1 calc R . . C8 C -0.0878(5) 0.1700(7) 0.58128(15) 0.0745(14) Uani 1 1 d . . . H8A H -0.1352 0.0845 0.5595 0.112 Uiso 1 1 calc R . . H8B H -0.1724 0.1965 0.5925 0.112 Uiso 1 1 calc R . . H8C H -0.0312 0.1373 0.6037 0.112 Uiso 1 1 calc R . . C9 C 0.4326(4) 0.1903(4) 0.47944(10) 0.0404(7) Uani 1 1 d . . . H9A H 0.3661 0.1637 0.4523 0.048 Uiso 1 1 calc R . . H9B H 0.4547 0.0974 0.4869 0.048 Uiso 1 1 calc R . . C10 C 0.5889(4) 0.3235(5) 0.47467(11) 0.0513(9) Uani 1 1 d . . . H10A H 0.5677 0.4134 0.4651 0.077 Uiso 1 1 calc R . . H10B H 0.6464 0.2904 0.4542 0.077 Uiso 1 1 calc R . . H10C H 0.6541 0.3530 0.5016 0.077 Uiso 1 1 calc R . . C11 C 0.1054(4) 0.2616(4) 0.46429(9) 0.0351(7) Uani 1 1 d . . . C12 C -0.0536(4) 0.1607(4) 0.45254(10) 0.0394(7) Uani 1 1 d . . . H12 H -0.1101 0.0872 0.4712 0.047 Uiso 1 1 calc R . . C13 C -0.1294(4) 0.1671(4) 0.41381(9) 0.0363(7) Uani 1 1 d . . . H13 H -0.2363 0.0964 0.4061 0.044 Uiso 1 1 calc R . . C14 C -0.0500(3) 0.2763(4) 0.38643(9) 0.0322(6) Uani 1 1 d . . . C15 C 0.1072(4) 0.3788(4) 0.39801(9) 0.0365(7) Uani 1 1 d . . . H15 H 0.1623 0.4548 0.3798 0.044 Uiso 1 1 calc R . . C16 C 0.1827(4) 0.3697(4) 0.43622(10) 0.0368(7) Uani 1 1 d . . . H16 H 0.2905 0.4390 0.4435 0.044 Uiso 1 1 calc R . . C17 C -0.3495(4) 0.2172(4) 0.33717(9) 0.0352(7) Uani 1 1 d . . . C18 C -0.4080(4) 0.3015(5) 0.36282(10) 0.0461(8) Uani 1 1 d . . . H18 H -0.3359 0.3898 0.3798 0.055 Uiso 1 1 calc R . . C19 C -0.5717(5) 0.2577(6) 0.36400(12) 0.0578(10) Uani 1 1 d . . . H19 H -0.6111 0.3157 0.3819 0.069 Uiso 1 1 calc R . . C20 C -0.6757(5) 0.1321(6) 0.33956(14) 0.0614(11) Uani 1 1 d . . . H20 H -0.7875 0.1038 0.3401 0.074 Uiso 1 1 calc R . . C21 C -0.6197(5) 0.0453(5) 0.31404(15) 0.0614(11) Uani 1 1 d . . . H21 H -0.6929 -0.0435 0.2975 0.074 Uiso 1 1 calc R . . C22 C -0.4557(4) 0.0878(4) 0.31258(12) 0.0488(9) Uani 1 1 d . . . H22 H -0.4168 0.0287 0.2949 0.059 Uiso 1 1 calc R . . C23 C -0.0880(4) 0.1679(4) 0.29985(9) 0.0364(7) Uani 1 1 d . . . C24 C -0.1136(4) 0.0153(4) 0.30809(11) 0.0452(8) Uani 1 1 d . . . H24 H -0.1624 -0.0257 0.3324 0.054 Uiso 1 1 calc R . . C25 C -0.0696(5) -0.0778(5) 0.28164(12) 0.0538(9) Uani 1 1 d . . . H25 H -0.0884 -0.1827 0.2875 0.065 Uiso 1 1 calc R . . C26 C 0.0029(5) -0.0168(5) 0.24624(12) 0.0594(11) Uani 1 1 d . . . H26 H 0.0358 -0.0796 0.2281 0.071 Uiso 1 1 calc R . . C27 C 0.0269(5) 0.1330(5) 0.23749(12) 0.0607(11) Uani 1 1 d . . . H27 H 0.0754 0.1733 0.2131 0.073 Uiso 1 1 calc R . . C28 C -0.0188(5) 0.2270(5) 0.26394(10) 0.0482(8) Uani 1 1 d . . . H28 H -0.0030 0.3307 0.2575 0.058 Uiso 1 1 calc R . . C29 C 0.2572(4) 0.1224(4) -0.04639(9) 0.0352(7) Uani 1 1 d . . . C30 C 0.2035(4) 0.2249(4) -0.06775(9) 0.0355(7) Uani 1 1 d . . . C31 C 0.1696(4) 0.2058(4) -0.11082(10) 0.0451(8) Uani 1 1 d . . . H31 H 0.1314 0.2734 -0.1256 0.054 Uiso 1 1 calc R . . C32 C 0.1944(5) 0.0814(4) -0.13172(11) 0.0501(9) Uani 1 1 d . . . H32 H 0.1717 0.0648 -0.1612 0.060 Uiso 1 1 calc R . . C33 C 0.2500(5) -0.0158(4) -0.11078(11) 0.0530(9) Uani 1 1 d . . . H33 H 0.2664 -0.0975 -0.1259 0.064 Uiso 1 1 calc R . . C34 C 0.2831(4) 0.0028(4) -0.06764(11) 0.0430(8) Uani 1 1 d . . . H34 H 0.3224 -0.0646 -0.0532 0.052 Uiso 1 1 calc R . . C35 C 0.3286(4) 0.0799(4) 0.02726(10) 0.0434(8) Uani 1 1 d . . . H35A H 0.3613 0.1437 0.0542 0.052 Uiso 1 1 calc R . . H35B H 0.4233 0.0635 0.0183 0.052 Uiso 1 1 calc R . . C36 C 0.2000(5) -0.0774(4) 0.03362(13) 0.0584(10) Uani 1 1 d . . . H36A H 0.1109 -0.0616 0.0456 0.088 Uiso 1 1 calc R . . H36B H 0.2444 -0.1338 0.0527 0.088 Uiso 1 1 calc R . . H36C H 0.1617 -0.1386 0.0067 0.088 Uiso 1 1 calc R . . C37 C 0.1391(5) 0.4584(4) -0.05160(12) 0.0471(8) Uani 1 1 d . . . H37A H 0.1101 0.5042 -0.0268 0.057 Uiso 1 1 calc R . . H37B H 0.0420 0.4120 -0.0715 0.057 Uiso 1 1 calc R . . C38 C 0.2649(6) 0.5873(5) -0.07178(15) 0.0695(12) Uani 1 1 d . . . H38A H 0.3588 0.6386 -0.0516 0.104 Uiso 1 1 calc R . . H38B H 0.2215 0.6642 -0.0808 0.104 Uiso 1 1 calc R . . H38C H 0.2960 0.5425 -0.0960 0.104 Uiso 1 1 calc R . . C39 C 0.2409(4) 0.3876(4) 0.04478(9) 0.0356(7) Uani 1 1 d . . . C40 C 0.1433(4) 0.3107(4) 0.07505(10) 0.0405(7) Uani 1 1 d . . . H40 H 0.0686 0.2065 0.0685 0.049 Uiso 1 1 calc R . . C41 C 0.1516(4) 0.3810(4) 0.11409(10) 0.0397(7) Uani 1 1 d . . . H41 H 0.0832 0.3257 0.1339 0.048 Uiso 1 1 calc R . . C42 C 0.2616(4) 0.5349(4) 0.12443(9) 0.0356(7) Uani 1 1 d . . . C43 C 0.3576(4) 0.6153(4) 0.09453(9) 0.0382(7) Uani 1 1 d . . . H43 H 0.4309 0.7201 0.1010 0.046 Uiso 1 1 calc R . . C44 C 0.3468(4) 0.5431(4) 0.05515(10) 0.0392(7) Uani 1 1 d . . . H44 H 0.4121 0.5999 0.0349 0.047 Uiso 1 1 calc R . . C45 C 0.4378(4) 0.5687(4) 0.20416(9) 0.0404(7) Uani 1 1 d . . . C46 C 0.4160(6) 0.5101(5) 0.24355(11) 0.0589(10) Uani 1 1 d . . . H46 H 0.3206 0.4947 0.2562 0.071 Uiso 1 1 calc R . . C47 C 0.5390(6) 0.4748(5) 0.26387(12) 0.0655(12) Uani 1 1 d . . . H47 H 0.5247 0.4325 0.2903 0.079 Uiso 1 1 calc R . . C48 C 0.6787(6) 0.4995(5) 0.24669(13) 0.0623(12) Uani 1 1 d . . . H48 H 0.7609 0.4766 0.2614 0.075 Uiso 1 1 calc R . . C49 C 0.7000(5) 0.5585(5) 0.20753(13) 0.0582(10) Uani 1 1 d . . . H49 H 0.7966 0.5759 0.1953 0.070 Uiso 1 1 calc R . . C50 C 0.5785(4) 0.5915(4) 0.18656(11) 0.0483(8) Uani 1 1 d . . . H50 H 0.5922 0.6304 0.1597 0.058 Uiso 1 1 calc R . . C51 C 0.3494(4) 0.8218(4) 0.17633(9) 0.0409(7) Uani 1 1 d . . . C52 C 0.4847(5) 0.9246(4) 0.19961(12) 0.0551(10) Uani 1 1 d . . . H52 H 0.5513 0.8860 0.2160 0.066 Uiso 1 1 calc R . . C53 C 0.5238(6) 1.0848(5) 0.19917(14) 0.0663(12) Uani 1 1 d . . . H53 H 0.6176 1.1552 0.2151 0.080 Uiso 1 1 calc R . . C54 C 0.4277(6) 1.1423(5) 0.17582(13) 0.0643(12) Uani 1 1 d . . . H54 H 0.4544 1.2519 0.1760 0.077 Uiso 1 1 calc R . . C55 C 0.2936(6) 1.0409(5) 0.15231(13) 0.0634(11) Uani 1 1 d . . . H55 H 0.2281 1.0802 0.1358 0.076 Uiso 1 1 calc R . . C56 C 0.2538(5) 0.8818(5) 0.15271(12) 0.0528(9) Uani 1 1 d . . . H56 H 0.1600 0.8121 0.1366 0.063 Uiso 1 1 calc R . . O3 O 0.1398(5) 0.6826(4) 0.27897(14) 0.0891(13) Uani 1 1 d . . . H3A H 0.091(8) 0.641(8) 0.250(2) 0.13(3) Uiso 1 1 d . . . H3B H 0.068(8) 0.606(8) 0.296(2) 0.12(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0324(4) 0.0375(4) 0.0290(4) 0.0055(3) 0.0033(3) 0.0156(3) P2 0.0488(5) 0.0378(4) 0.0294(4) 0.0046(3) 0.0059(3) 0.0177(4) O1 0.0454(13) 0.0408(12) 0.0411(12) 0.0111(10) 0.0057(10) 0.0172(10) O2 0.0602(16) 0.0560(16) 0.0426(13) 0.0085(11) 0.0179(12) 0.0181(13) N1 0.0326(13) 0.0449(15) 0.0362(13) 0.0035(11) 0.0021(11) 0.0200(11) N2 0.0357(13) 0.0406(14) 0.0287(12) 0.0050(10) 0.0040(10) 0.0175(11) N3 0.0413(14) 0.0341(13) 0.0317(12) 0.0021(10) 0.0017(11) 0.0154(11) N4 0.0425(14) 0.0332(13) 0.0348(13) 0.0023(11) 0.0038(11) 0.0166(11) B1 0.0361(18) 0.0318(17) 0.0360(17) 0.0055(14) 0.0004(14) 0.0143(14) B2 0.0336(17) 0.0321(17) 0.0360(17) 0.0018(14) 0.0032(14) 0.0112(14) C1 0.0316(15) 0.0381(16) 0.0348(15) 0.0063(12) 0.0009(12) 0.0144(13) C2 0.0365(16) 0.0346(16) 0.0338(15) 0.0063(12) -0.0006(12) 0.0156(13) C3 0.0360(16) 0.056(2) 0.0411(17) 0.0095(15) 0.0051(14) 0.0257(15) C4 0.0410(18) 0.064(2) 0.0427(18) 0.0156(17) -0.0018(15) 0.0226(17) C5 0.0453(19) 0.065(2) 0.0316(16) 0.0066(15) 0.0002(14) 0.0182(17) C6 0.0450(18) 0.0474(19) 0.0355(16) 0.0069(14) 0.0057(14) 0.0200(15) C7 0.047(2) 0.074(3) 0.0454(19) -0.0033(18) -0.0004(16) 0.0401(19) C8 0.042(2) 0.114(4) 0.073(3) 0.014(3) 0.017(2) 0.033(2) C9 0.0439(18) 0.0494(19) 0.0344(15) -0.0017(14) 0.0002(13) 0.0264(15) C10 0.0420(19) 0.072(3) 0.0390(18) 0.0003(17) 0.0079(15) 0.0206(18) C11 0.0365(16) 0.0405(17) 0.0326(15) 0.0027(13) 0.0017(12) 0.0198(13) C12 0.0395(17) 0.0409(17) 0.0357(16) 0.0074(13) 0.0000(13) 0.0133(14) C13 0.0337(16) 0.0387(17) 0.0357(15) 0.0052(13) -0.0010(12) 0.0135(13) C14 0.0320(15) 0.0389(16) 0.0314(14) 0.0005(12) 0.0031(12) 0.0203(13) C15 0.0338(16) 0.0419(17) 0.0325(15) 0.0039(13) 0.0062(12) 0.0122(13) C16 0.0313(15) 0.0415(17) 0.0375(16) 0.0017(13) 0.0002(12) 0.0146(13) C17 0.0353(16) 0.0458(18) 0.0305(14) 0.0115(13) 0.0026(12) 0.0215(14) C18 0.0401(18) 0.068(2) 0.0340(16) 0.0050(16) 0.0048(14) 0.0248(17) C19 0.047(2) 0.095(3) 0.046(2) 0.016(2) 0.0135(17) 0.041(2) C20 0.0351(19) 0.089(3) 0.067(2) 0.032(2) 0.0128(18) 0.028(2) C21 0.040(2) 0.056(2) 0.082(3) 0.013(2) -0.011(2) 0.0133(17) C22 0.0403(18) 0.048(2) 0.059(2) 0.0008(17) -0.0072(16) 0.0202(16) C23 0.0349(16) 0.0443(18) 0.0327(15) 0.0015(13) 0.0022(12) 0.0186(13) C24 0.0478(19) 0.049(2) 0.0418(17) 0.0019(15) 0.0026(15) 0.0225(16) C25 0.059(2) 0.050(2) 0.056(2) -0.0065(18) -0.0025(18) 0.0278(18) C26 0.065(3) 0.073(3) 0.048(2) -0.0145(19) 0.0066(19) 0.037(2) C27 0.076(3) 0.069(3) 0.0390(19) -0.0001(18) 0.0176(19) 0.029(2) C28 0.059(2) 0.050(2) 0.0364(17) 0.0038(15) 0.0098(16) 0.0216(17) C29 0.0372(16) 0.0302(15) 0.0352(15) 0.0011(12) 0.0055(13) 0.0094(12) C30 0.0368(16) 0.0316(15) 0.0352(15) 0.0015(12) 0.0063(13) 0.0095(13) C31 0.052(2) 0.0447(19) 0.0348(16) 0.0037(14) 0.0002(15) 0.0152(16) C32 0.062(2) 0.047(2) 0.0324(16) -0.0020(15) 0.0065(16) 0.0110(17) C33 0.070(3) 0.0393(19) 0.0454(19) -0.0061(16) 0.0128(18) 0.0159(18) C34 0.0489(19) 0.0340(17) 0.0463(18) 0.0023(14) 0.0089(15) 0.0155(14) C35 0.0493(19) 0.0458(19) 0.0391(17) 0.0064(14) -0.0009(15) 0.0233(16) C36 0.078(3) 0.042(2) 0.055(2) 0.0149(17) 0.005(2) 0.0220(19) C37 0.058(2) 0.0424(19) 0.0495(19) 0.0064(15) 0.0021(16) 0.0293(17) C38 0.095(3) 0.040(2) 0.075(3) 0.019(2) 0.011(2) 0.026(2) C39 0.0400(17) 0.0358(16) 0.0317(14) 0.0021(12) -0.0008(13) 0.0162(13) C40 0.0478(19) 0.0316(16) 0.0387(16) -0.0003(13) 0.0010(14) 0.0123(14) C41 0.0453(18) 0.0359(17) 0.0350(16) 0.0068(13) 0.0070(14) 0.0116(14) C42 0.0421(17) 0.0367(16) 0.0298(14) 0.0055(12) 0.0028(12) 0.0172(13) C43 0.0449(18) 0.0327(16) 0.0330(15) 0.0020(12) 0.0012(13) 0.0110(13) C44 0.0454(18) 0.0360(17) 0.0335(15) 0.0025(13) 0.0027(13) 0.0130(14) C45 0.061(2) 0.0306(16) 0.0305(15) 0.0036(12) -0.0035(14) 0.0194(15) C46 0.084(3) 0.066(3) 0.0328(17) 0.0114(17) 0.0067(18) 0.035(2) C47 0.103(4) 0.067(3) 0.0364(19) 0.0127(18) -0.004(2) 0.045(3) C48 0.084(3) 0.048(2) 0.053(2) 0.0032(18) -0.024(2) 0.029(2) C49 0.053(2) 0.055(2) 0.062(2) 0.0126(19) -0.0064(19) 0.0167(18) C50 0.052(2) 0.047(2) 0.0452(18) 0.0168(16) 0.0022(16) 0.0188(16) C51 0.055(2) 0.0429(18) 0.0297(15) 0.0035(13) 0.0103(14) 0.0229(16) C52 0.072(3) 0.044(2) 0.051(2) -0.0027(17) -0.0058(19) 0.0273(19) C53 0.081(3) 0.043(2) 0.069(3) -0.007(2) -0.006(2) 0.021(2) C54 0.105(4) 0.040(2) 0.059(2) 0.0041(18) 0.013(2) 0.038(2) C55 0.094(3) 0.055(2) 0.059(2) 0.008(2) 0.003(2) 0.049(2) C56 0.066(2) 0.050(2) 0.050(2) 0.0035(17) -0.0019(18) 0.0318(19) O3 0.113(3) 0.0492(18) 0.093(3) -0.0001(18) 0.062(2) 0.0089(18) _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 1.489(2) . ? P1 C17 1.801(3) . ? P1 C23 1.802(3) . ? P1 C14 1.808(3) . ? P2 O2 1.492(3) . ? P2 C45 1.801(4) . ? P2 C51 1.807(4) . ? P2 C42 1.811(3) . ? N1 C1 1.405(4) . ? N1 B1 1.426(4) . ? N1 C7 1.452(4) . ? N2 C2 1.406(4) . ? N2 B1 1.438(4) . ? N2 C9 1.455(4) . ? N3 C29 1.401(4) . ? N3 B2 1.436(5) . ? N3 C35 1.457(4) . ? N4 C30 1.395(4) . ? N4 B2 1.437(4) . ? N4 C37 1.453(4) . ? B1 C11 1.574(4) . ? B2 C39 1.563(5) . ? C1 C6 1.391(4) . ? C1 C2 1.394(4) . ? C2 C3 1.386(4) . ? C3 C4 1.393(5) . ? C3 H3 0.9500 . ? C4 C5 1.379(5) . ? C4 H4 0.9500 . ? C5 C6 1.389(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.525(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.510(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.396(4) . ? C11 C12 1.403(4) . ? C12 C13 1.395(4) . ? C12 H12 0.9500 . ? C13 C14 1.391(4) . ? C13 H13 0.9500 . ? C14 C15 1.394(4) . ? C15 C16 1.386(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.382(5) . ? C17 C22 1.389(5) . ? C18 C19 1.390(5) . ? C18 H18 0.9500 . ? C19 C20 1.361(6) . ? C19 H19 0.9500 . ? C20 C21 1.381(7) . ? C20 H20 0.9500 . ? C21 C22 1.395(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.383(5) . ? C23 C28 1.391(5) . ? C24 C25 1.375(5) . ? C24 H24 0.9500 . ? C25 C26 1.392(6) . ? C25 H25 0.9500 . ? C26 C27 1.365(6) . ? C26 H26 0.9500 . ? C27 C28 1.389(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.385(5) . ? C29 C30 1.403(5) . ? C30 C31 1.389(4) . ? C31 C32 1.413(5) . ? C31 H31 0.9500 . ? C32 C33 1.365(6) . ? C32 H32 0.9500 . ? C33 C34 1.391(5) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.517(5) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C38 1.515(6) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.398(5) . ? C39 C44 1.406(4) . ? C40 C41 1.378(4) . ? C40 H40 0.9500 . ? C41 C42 1.405(4) . ? C41 H41 0.9500 . ? C42 C43 1.392(4) . ? C43 C44 1.391(4) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C50 1.384(5) . ? C45 C46 1.399(5) . ? C46 C47 1.403(6) . ? C46 H46 0.9500 . ? C47 C48 1.366(7) . ? C47 H47 0.9500 . ? C48 C49 1.393(6) . ? C48 H48 0.9500 . ? C49 C50 1.389(5) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 C52 1.378(5) . ? C51 C56 1.394(5) . ? C52 C53 1.391(6) . ? C52 H52 0.9500 . ? C53 C54 1.378(6) . ? C53 H53 0.9500 . ? C54 C55 1.371(6) . ? C54 H54 0.9500 . ? C55 C56 1.380(6) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? O3 H3A 1.01(7) . ? O3 H3B 0.98(7) . ? 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 C17 112.15(14) . . ? O1 P1 C23 112.84(14) . . ? C17 P1 C23 108.26(15) . . ? O1 P1 C14 110.76(14) . . ? C17 P1 C14 106.60(14) . . ? C23 P1 C14 105.84(14) . . ? O2 P2 C45 113.10(16) . . ? O2 P2 C51 113.31(16) . . ? C45 P2 C51 107.29(16) . . ? O2 P2 C42 111.58(15) . . ? C45 P2 C42 104.93(15) . . ? C51 P2 C42 106.02(14) . . ? C1 N1 B1 108.1(3) . . ? C1 N1 C7 121.0(3) . . ? B1 N1 C7 130.9(3) . . ? C2 N2 B1 107.6(3) . . ? C2 N2 C9 121.8(3) . . ? B1 N2 C9 130.6(3) . . ? C29 N3 B2 108.0(3) . . ? C29 N3 C35 122.0(3) . . ? B2 N3 C35 130.0(3) . . ? C30 N4 B2 107.9(3) . . ? C30 N4 C37 122.2(3) . . ? B2 N4 C37 129.9(3) . . ? N1 B1 N2 106.8(3) . . ? N1 B1 C11 128.4(3) . . ? N2 B1 C11 124.8(3) . . ? N3 B2 N4 106.5(3) . . ? N3 B2 C39 125.4(3) . . ? N4 B2 C39 128.2(3) . . ? C6 C1 C2 120.9(3) . . ? C6 C1 N1 130.4(3) . . ? C2 C1 N1 108.7(3) . . ? C3 C2 C1 120.9(3) . . ? C3 C2 N2 130.2(3) . . ? C1 C2 N2 108.9(3) . . ? C2 C3 C4 117.9(3) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 121.1(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 117.7(3) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? N1 C7 C8 111.5(3) . . ? N1 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 113.3(3) . . ? N2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 117.6(3) . . ? C16 C11 B1 119.7(3) . . ? C12 C11 B1 122.7(3) . . ? C13 C12 C11 120.7(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.2(3) . . ? C13 C14 P1 124.4(2) . . ? C15 C14 P1 116.4(2) . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 122.0(3) . . ? C15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? C18 C17 C22 119.5(3) . . ? C18 C17 P1 116.1(3) . . ? C22 C17 P1 124.3(3) . . ? C17 C18 C19 120.4(4) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 120.1(4) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 119.5(4) . . ? C17 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C28 119.4(3) . . ? C24 C23 P1 121.5(2) . . ? C28 C23 P1 119.0(3) . . ? C25 C24 C23 121.0(3) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C24 C25 C26 119.3(4) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C27 C26 C25 120.3(4) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 120.6(4) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 119.4(4) . . ? C27 C28 H28 120.3 . . ? C23 C28 H28 120.3 . . ? C34 C29 N3 130.4(3) . . ? C34 C29 C30 121.1(3) . . ? N3 C29 C30 108.5(3) . . ? C31 C30 N4 130.2(3) . . ? C31 C30 C29 120.7(3) . . ? N4 C30 C29 109.0(3) . . ? C30 C31 C32 117.1(3) . . ? C30 C31 H31 121.5 . . ? C32 C31 H31 121.5 . . ? C33 C32 C31 121.8(3) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.1 . . ? C32 C33 C34 121.1(3) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C29 C34 C33 118.1(3) . . ? C29 C34 H34 120.9 . . ? C33 C34 H34 120.9 . . ? N3 C35 C36 113.2(3) . . ? N3 C35 H35A 108.9 . . ? C36 C35 H35A 108.9 . . ? N3 C35 H35B 108.9 . . ? C36 C35 H35B 108.9 . . ? H35A C35 H35B 107.8 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N4 C37 C38 113.0(3) . . ? N4 C37 H37A 109.0 . . ? C38 C37 H37A 109.0 . . ? N4 C37 H37B 109.0 . . ? C38 C37 H37B 109.0 . . ? H37A C37 H37B 107.8 . . ? 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 . . ? C40 C39 C44 117.4(3) . . ? C40 C39 B2 120.8(3) . . ? C44 C39 B2 121.8(3) . . ? C41 C40 C39 122.2(3) . . ? C41 C40 H40 118.9 . . ? C39 C40 H40 118.9 . . ? C40 C41 C42 119.8(3) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C43 C42 C41 119.2(3) . . ? C43 C42 P2 123.7(2) . . ? C41 C42 P2 117.0(2) . . ? C44 C43 C42 120.3(3) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C39 121.1(3) . . ? C43 C44 H44 119.4 . . ? C39 C44 H44 119.4 . . ? C50 C45 C46 119.8(3) . . ? C50 C45 P2 122.0(2) . . ? C46 C45 P2 118.1(3) . . ? C45 C46 C47 118.2(4) . . ? C45 C46 H46 120.9 . . ? C47 C46 H46 120.9 . . ? C48 C47 C46 121.9(4) . . ? C48 C47 H47 119.1 . . ? C46 C47 H47 119.1 . . ? C47 C48 C49 119.7(4) . . ? C47 C48 H48 120.2 . . ? C49 C48 H48 120.2 . . ? C50 C49 C48 119.3(4) . . ? C50 C49 H49 120.3 . . ? C48 C49 H49 120.3 . . ? C45 C50 C49 121.1(3) . . ? C45 C50 H50 119.5 . . ? C49 C50 H50 119.5 . . ? C52 C51 C56 118.7(3) . . ? C52 C51 P2 123.6(3) . . ? C56 C51 P2 117.5(3) . . ? C51 C52 C53 120.0(4) . . ? C51 C52 H52 120.0 . . ? C53 C52 H52 120.0 . . ? C54 C53 C52 120.6(4) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C55 C54 C53 119.8(4) . . ? C55 C54 H54 120.1 . . ? C53 C54 H54 120.1 . . ? C54 C55 C56 119.9(4) . . ? C54 C55 H55 120.1 . . ? C56 C55 H55 120.1 . . ? C55 C56 C51 121.0(4) . . ? C55 C56 H56 119.5 . . ? C51 C56 H56 119.5 . . ? H3A O3 H3B 103(5) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.779 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.071 #============================================================================== data_compound4 _database_code_depnum_ccdc_archive 'CCDC 873270' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 B N2 P S' _chemical_formula_sum 'C28 H28 B N2 P S' _chemical_formula_weight 466.36 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.14690(10) _cell_length_b 15.2300(2) _cell_length_c 32.2144(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.0472(5) _cell_angle_gamma 90.00 _cell_volume 4940.72(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 81882 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.508 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9383 _exptl_absorpt_correction_T_max 0.9747 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44387 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7175 _reflns_number_gt 5759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.8927P] 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 7175 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 S1 S 0.01989(3) 0.532146(19) 0.185882(9) 0.02409(8) Uani 1 1 d . . . P1 P 0.17014(3) 0.463913(18) 0.170404(9) 0.01715(7) Uani 1 1 d . . . N1 N -0.03109(9) 0.19200(6) -0.00474(3) 0.01776(18) Uani 1 1 d . . . N2 N 0.03125(9) 0.30955(6) -0.04253(3) 0.01836(19) Uani 1 1 d . . . B1 B 0.02407(12) 0.27899(8) -0.00082(4) 0.0187(2) Uani 1 1 d . . . C1 C -0.05567(10) 0.17181(7) -0.04733(3) 0.0178(2) Uani 1 1 d . . . C2 C -0.01818(10) 0.24405(7) -0.07046(3) 0.0177(2) Uani 1 1 d . . . C3 C -0.03377(11) 0.24236(8) -0.11401(3) 0.0219(2) Uani 1 1 d . . . H3 H -0.0101 0.2915 -0.1297 0.026 Uiso 1 1 calc R . . C4 C -0.08536(12) 0.16609(8) -0.13387(4) 0.0245(2) Uani 1 1 d . . . H4 H -0.0969 0.1633 -0.1636 0.029 Uiso 1 1 calc R . . C5 C -0.12015(12) 0.09426(8) -0.11096(4) 0.0247(2) Uani 1 1 d . . . H5 H -0.1540 0.0429 -0.1253 0.030 Uiso 1 1 calc R . . C6 C -0.10636(11) 0.09608(8) -0.06734(4) 0.0213(2) Uani 1 1 d . . . H6 H -0.1309 0.0470 -0.0518 0.026 Uiso 1 1 calc R . . C7 C -0.06286(11) 0.13043(7) 0.02722(3) 0.0197(2) Uani 1 1 d . . . H7A H -0.0173 0.1494 0.0547 0.024 Uiso 1 1 calc R . . H7B H -0.0283 0.0717 0.0210 0.024 Uiso 1 1 calc R . . C8 C -0.21150(12) 0.12332(8) 0.03003(4) 0.0258(2) Uani 1 1 d . . . H8A H -0.2454 0.1804 0.0379 0.039 Uiso 1 1 calc R . . H8B H -0.2270 0.0794 0.0511 0.039 Uiso 1 1 calc R . . H8C H -0.2576 0.1055 0.0028 0.039 Uiso 1 1 calc R . . C9 C 0.07590(12) 0.39364(8) -0.05748(4) 0.0242(2) Uani 1 1 d . . . H9A H 0.0827 0.4368 -0.0343 0.029 Uiso 1 1 calc R . . H9B H 0.0092 0.4157 -0.0801 0.029 Uiso 1 1 calc R . . C10 C 0.20949(13) 0.38615(10) -0.07385(4) 0.0347(3) Uani 1 1 d . . . H10A H 0.2782 0.3723 -0.0507 0.052 Uiso 1 1 calc R . . H10B H 0.2308 0.4419 -0.0866 0.052 Uiso 1 1 calc R . . H10C H 0.2057 0.3393 -0.0948 0.052 Uiso 1 1 calc R . . C11 C 0.06443(11) 0.32934(7) 0.04123(3) 0.0183(2) Uani 1 1 d . . . C12 C -0.02986(11) 0.34357(7) 0.06906(3) 0.0199(2) Uani 1 1 d . . . H12 H -0.1183 0.3236 0.0617 0.024 Uiso 1 1 calc R . . C13 C 0.00302(11) 0.38595(7) 0.10704(3) 0.0196(2) Uani 1 1 d . . . H13 H -0.0631 0.3956 0.1250 0.023 Uiso 1 1 calc R . . C14 C 0.13314(11) 0.41450(7) 0.11898(3) 0.0175(2) Uani 1 1 d . . . C15 C 0.22857(11) 0.40146(7) 0.09167(3) 0.0194(2) Uani 1 1 d . . . H15 H 0.3173 0.4208 0.0993 0.023 Uiso 1 1 calc R . . C16 C 0.19363(11) 0.36022(7) 0.05333(3) 0.0197(2) Uani 1 1 d . . . H16 H 0.2590 0.3528 0.0349 0.024 Uiso 1 1 calc R . . C17 C 0.21726(11) 0.37280(7) 0.20540(3) 0.0192(2) Uani 1 1 d . . . C18 C 0.30002(12) 0.30591(8) 0.19383(4) 0.0232(2) Uani 1 1 d . . . H18 H 0.3327 0.3080 0.1675 0.028 Uiso 1 1 calc R . . C19 C 0.33423(13) 0.23656(8) 0.22100(4) 0.0294(3) Uani 1 1 d . . . H19 H 0.3924 0.1919 0.2135 0.035 Uiso 1 1 calc R . . C20 C 0.28357(14) 0.23236(9) 0.25907(4) 0.0338(3) Uani 1 1 d . . . H20 H 0.3048 0.1839 0.2772 0.041 Uiso 1 1 calc R . . C21 C 0.20225(14) 0.29867(10) 0.27052(4) 0.0337(3) Uani 1 1 d . . . H21 H 0.1681 0.2957 0.2967 0.040 Uiso 1 1 calc R . . C22 C 0.17014(12) 0.36959(9) 0.24410(4) 0.0252(2) Uani 1 1 d . . . H22 H 0.1162 0.4157 0.2525 0.030 Uiso 1 1 calc R . . C23 C 0.31842(12) 0.52961(7) 0.16877(3) 0.0211(2) Uani 1 1 d . . . C24 C 0.43822(13) 0.51140(9) 0.19318(4) 0.0295(3) Uani 1 1 d . . . H24 H 0.4467 0.4606 0.2104 0.035 Uiso 1 1 calc R . . C25 C 0.54577(15) 0.56808(11) 0.19227(5) 0.0407(3) Uani 1 1 d . . . H25 H 0.6275 0.5560 0.2090 0.049 Uiso 1 1 calc R . . C26 C 0.53366(16) 0.64180(10) 0.16705(5) 0.0409(4) Uani 1 1 d . . . H26 H 0.6073 0.6801 0.1664 0.049 Uiso 1 1 calc R . . C27 C 0.41466(15) 0.66010(9) 0.14274(4) 0.0358(3) Uani 1 1 d . . . H27 H 0.4070 0.7107 0.1254 0.043 Uiso 1 1 calc R . . C28 C 0.30687(13) 0.60477(8) 0.14374(4) 0.0278(3) Uani 1 1 d . . . H28 H 0.2249 0.6179 0.1274 0.033 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 S1 0.02745(16) 0.02107(15) 0.02480(15) -0.00163(11) 0.00745(11) 0.00318(11) P1 0.02034(14) 0.01631(14) 0.01508(13) -0.00079(10) 0.00323(10) -0.00095(10) N1 0.0189(4) 0.0192(4) 0.0150(4) -0.0002(3) 0.0010(3) -0.0018(3) N2 0.0190(4) 0.0171(4) 0.0187(4) -0.0010(4) 0.0012(3) -0.0025(3) B1 0.0164(5) 0.0192(6) 0.0202(6) -0.0010(5) 0.0009(4) 0.0005(4) C1 0.0151(5) 0.0207(5) 0.0174(5) -0.0012(4) 0.0010(4) -0.0008(4) C2 0.0157(5) 0.0188(5) 0.0184(5) -0.0012(4) 0.0012(4) -0.0005(4) C3 0.0223(5) 0.0246(6) 0.0187(5) 0.0017(4) 0.0026(4) -0.0016(4) C4 0.0255(6) 0.0306(6) 0.0170(5) -0.0035(5) 0.0018(4) -0.0038(5) C5 0.0257(6) 0.0252(6) 0.0228(6) -0.0059(5) 0.0015(4) -0.0060(5) C6 0.0224(5) 0.0194(5) 0.0220(5) -0.0013(4) 0.0028(4) -0.0035(4) C7 0.0219(5) 0.0192(5) 0.0176(5) 0.0029(4) 0.0007(4) -0.0011(4) C8 0.0240(6) 0.0304(6) 0.0227(6) 0.0039(5) 0.0021(4) -0.0056(5) C9 0.0305(6) 0.0181(5) 0.0231(5) 0.0020(5) -0.0002(4) -0.0054(4) C10 0.0328(7) 0.0382(7) 0.0338(7) 0.0025(6) 0.0066(5) -0.0173(6) C11 0.0211(5) 0.0158(5) 0.0175(5) 0.0008(4) 0.0005(4) 0.0002(4) C12 0.0188(5) 0.0199(5) 0.0206(5) 0.0009(4) 0.0010(4) -0.0032(4) C13 0.0200(5) 0.0199(5) 0.0194(5) 0.0004(4) 0.0044(4) -0.0011(4) C14 0.0208(5) 0.0157(5) 0.0158(5) 0.0010(4) 0.0015(4) -0.0004(4) C15 0.0181(5) 0.0204(5) 0.0193(5) -0.0013(4) 0.0012(4) -0.0024(4) C16 0.0200(5) 0.0218(5) 0.0175(5) -0.0016(4) 0.0031(4) -0.0006(4) C17 0.0194(5) 0.0202(5) 0.0174(5) 0.0010(4) -0.0004(4) -0.0033(4) C18 0.0249(6) 0.0223(6) 0.0220(5) -0.0007(5) 0.0014(4) -0.0006(4) C19 0.0287(6) 0.0241(6) 0.0331(7) 0.0003(5) -0.0055(5) 0.0030(5) C20 0.0346(7) 0.0320(7) 0.0320(7) 0.0129(6) -0.0068(5) -0.0011(6) C21 0.0328(7) 0.0447(8) 0.0233(6) 0.0116(6) 0.0026(5) 0.0005(6) C22 0.0237(6) 0.0314(6) 0.0208(5) 0.0035(5) 0.0040(4) 0.0014(5) C23 0.0264(6) 0.0200(5) 0.0175(5) -0.0052(4) 0.0057(4) -0.0056(4) C24 0.0298(6) 0.0311(7) 0.0266(6) -0.0013(5) -0.0005(5) -0.0087(5) C25 0.0339(7) 0.0494(9) 0.0377(8) -0.0065(7) -0.0006(6) -0.0178(6) C26 0.0458(8) 0.0437(8) 0.0353(7) -0.0117(7) 0.0130(6) -0.0267(7) C27 0.0539(9) 0.0288(7) 0.0270(6) -0.0030(5) 0.0140(6) -0.0171(6) C28 0.0377(7) 0.0248(6) 0.0220(6) -0.0013(5) 0.0084(5) -0.0059(5) _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 S1 P1 1.9595(4) . ? P1 C23 1.8130(11) . ? P1 C17 1.8145(11) . ? P1 C14 1.8164(11) . ? N1 C1 1.3982(13) . ? N1 B1 1.4378(15) . ? N1 C7 1.4576(14) . ? N2 C2 1.3948(14) . ? N2 B1 1.4324(15) . ? N2 C9 1.4599(14) . ? B1 C11 1.5667(16) . ? C1 C6 1.3889(15) . ? C1 C2 1.4072(15) . ? C2 C3 1.3926(15) . ? C3 C4 1.3965(16) . ? C3 H3 0.9500 . ? C4 C5 1.3893(17) . ? C4 H4 0.9500 . ? C5 C6 1.3952(16) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5258(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5178(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.4022(15) . ? C11 C12 1.4058(15) . ? C12 C13 1.3873(15) . ? C12 H12 0.9500 . ? C13 C14 1.3984(15) . ? C13 H13 0.9500 . ? C14 C15 1.4000(15) . ? C15 C16 1.3921(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.3900(15) . ? C17 C18 1.3995(16) . ? C18 C19 1.3883(17) . ? C18 H18 0.9500 . ? C19 C20 1.388(2) . ? C19 H19 0.9500 . ? C20 C21 1.383(2) . ? C20 H20 0.9500 . ? C21 C22 1.3889(18) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.3923(17) . ? C23 C28 1.3968(17) . ? C24 C25 1.3945(18) . ? C24 H24 0.9500 . ? C25 C26 1.382(2) . ? C25 H25 0.9500 . ? C26 C27 1.384(2) . ? C26 H26 0.9500 . ? C27 C28 1.3842(18) . ? C27 H27 0.9500 . ? C28 H28 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 C23 P1 C17 106.48(5) . . ? C23 P1 C14 106.36(5) . . ? C17 P1 C14 105.01(5) . . ? C23 P1 S1 112.90(4) . . ? C17 P1 S1 113.67(4) . . ? C14 P1 S1 111.81(4) . . ? C1 N1 B1 108.03(9) . . ? C1 N1 C7 121.56(9) . . ? B1 N1 C7 130.40(9) . . ? C2 N2 B1 108.49(9) . . ? C2 N2 C9 121.08(9) . . ? B1 N2 C9 130.40(9) . . ? N2 B1 N1 106.32(9) . . ? N2 B1 C11 127.90(10) . . ? N1 B1 C11 125.78(10) . . ? C6 C1 N1 130.49(10) . . ? C6 C1 C2 120.81(10) . . ? N1 C1 C2 108.69(9) . . ? C3 C2 N2 130.58(10) . . ? C3 C2 C1 120.96(10) . . ? N2 C2 C1 108.47(9) . . ? C2 C3 C4 117.82(11) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 121.13(11) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.25(11) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.01(11) . . ? C1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? N1 C7 C8 113.17(9) . . ? N1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 112.03(10) . . ? N2 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N2 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 117.21(10) . . ? C16 C11 B1 122.74(10) . . ? C12 C11 B1 120.04(10) . . ? C13 C12 C11 121.69(10) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 120.26(10) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 119.05(10) . . ? C13 C14 P1 117.53(8) . . ? C15 C14 P1 123.39(8) . . ? C16 C15 C14 120.06(10) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.71(10) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? C22 C17 C18 119.79(11) . . ? C22 C17 P1 119.40(9) . . ? C18 C17 P1 120.82(8) . . ? C19 C18 C17 119.86(11) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 120.06(12) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.00(12) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 120.48(12) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 119.77(12) . . ? C21 C22 H22 120.1 . . ? C17 C22 H22 120.1 . . ? C24 C23 C28 119.66(11) . . ? C24 C23 P1 122.95(9) . . ? C28 C23 P1 117.25(9) . . ? C23 C24 C25 119.74(13) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 120.12(14) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 120.29(12) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 120.07(13) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C23 120.11(13) . . ? C27 C28 H28 119.9 . . ? C23 C28 H28 119.9 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.364 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.047 #============================================================================== data_compound5 _database_code_depnum_ccdc_archive 'CCDC 873271' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 B N2 P Se' _chemical_formula_sum 'C28 H28 B N2 P Se' _chemical_formula_weight 513.26 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.09750(10) _cell_length_b 15.38000(10) _cell_length_c 32.4025(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.9366(5) _cell_angle_gamma 90.00 _cell_volume 4983.89(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 116385 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description column _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 1.590 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6470 _exptl_absorpt_correction_T_max 0.7850 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58689 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7227 _reflns_number_gt 5990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+3.2223P] 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 7227 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.005 _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 Se1 Se 0.506465(14) 0.538805(9) 0.684275(4) 0.02050(5) Uani 1 1 d . . . P1 P 0.67020(3) 0.46532(2) 0.669231(10) 0.01500(7) Uani 1 1 d . . . N1 N 0.53107(11) 0.30655(7) 0.45807(3) 0.0158(2) Uani 1 1 d . . . N2 N 0.46822(11) 0.19097(7) 0.49583(3) 0.0157(2) Uani 1 1 d . . . B1 B 0.52372(14) 0.27689(10) 0.49956(5) 0.0163(3) Uani 1 1 d . . . C1 C 0.48120(13) 0.24117(9) 0.43034(4) 0.0157(2) Uani 1 1 d . . . C2 C 0.44293(13) 0.17001(9) 0.45346(4) 0.0161(2) Uani 1 1 d . . . C3 C 0.39206(14) 0.09467(9) 0.43376(4) 0.0186(3) Uani 1 1 d . . . H3 H 0.3677 0.0464 0.4494 0.022 Uiso 1 1 calc R . . C4 C 0.37768(15) 0.09175(10) 0.39033(4) 0.0222(3) Uani 1 1 d . . . H4 H 0.3431 0.0408 0.3762 0.027 Uiso 1 1 calc R . . C5 C 0.41343(14) 0.16264(10) 0.36740(4) 0.0220(3) Uani 1 1 d . . . H5 H 0.4022 0.1593 0.3379 0.026 Uiso 1 1 calc R . . C6 C 0.46538(14) 0.23840(9) 0.38711(4) 0.0192(3) Uani 1 1 d . . . H6 H 0.4892 0.2867 0.3714 0.023 Uiso 1 1 calc R . . C7 C 0.57512(15) 0.38976(9) 0.44301(4) 0.0213(3) Uani 1 1 d . . . H7A H 0.5807 0.4330 0.4658 0.026 Uiso 1 1 calc R . . H7B H 0.5080 0.4107 0.4200 0.026 Uiso 1 1 calc R . . C8 C 0.71028(16) 0.38300(12) 0.42771(5) 0.0304(4) Uani 1 1 d . . . H8A H 0.7791 0.3697 0.4512 0.046 Uiso 1 1 calc R . . H8B H 0.7314 0.4384 0.4151 0.046 Uiso 1 1 calc R . . H8C H 0.7075 0.3366 0.4069 0.046 Uiso 1 1 calc R . . C9 C 0.43651(13) 0.13036(9) 0.52787(4) 0.0179(3) Uani 1 1 d . . . H9A H 0.4830 0.1495 0.5553 0.021 Uiso 1 1 calc R . . H9B H 0.4710 0.0720 0.5220 0.021 Uiso 1 1 calc R . . C10 C 0.28683(14) 0.12355(10) 0.53026(5) 0.0230(3) Uani 1 1 d . . . H10A H 0.2533 0.1800 0.5383 0.035 Uiso 1 1 calc R . . H10B H 0.2715 0.0797 0.5510 0.035 Uiso 1 1 calc R . . H10C H 0.2397 0.1066 0.5030 0.035 Uiso 1 1 calc R . . C11 C 0.56454(13) 0.32792(9) 0.54134(4) 0.0163(3) Uani 1 1 d . . . C12 C 0.69367(13) 0.36067(9) 0.55331(4) 0.0175(3) Uani 1 1 d . . . H12 H 0.7589 0.3538 0.5351 0.021 Uiso 1 1 calc R . . C13 C 0.72891(13) 0.40310(9) 0.59133(4) 0.0176(3) Uani 1 1 d . . . H13 H 0.8175 0.4239 0.5990 0.021 Uiso 1 1 calc R . . C14 C 0.63293(13) 0.41484(9) 0.61816(4) 0.0161(2) Uani 1 1 d . . . C15 C 0.50284(13) 0.38435(9) 0.60630(4) 0.0180(3) Uani 1 1 d . . . H15 H 0.4365 0.3934 0.6240 0.022 Uiso 1 1 calc R . . C16 C 0.47042(13) 0.34099(9) 0.56885(4) 0.0179(3) Uani 1 1 d . . . H16 H 0.3821 0.3195 0.5615 0.021 Uiso 1 1 calc R . . C17 C 0.81918(14) 0.53081(9) 0.66829(4) 0.0194(3) Uani 1 1 d . . . C18 C 0.80724(17) 0.60599(10) 0.64381(5) 0.0268(3) Uani 1 1 d . . . H18 H 0.7243 0.6198 0.6275 0.032 Uiso 1 1 calc R . . C19 C 0.9164(2) 0.66037(12) 0.64334(5) 0.0361(4) Uani 1 1 d . . . H19 H 0.9085 0.7111 0.6265 0.043 Uiso 1 1 calc R . . C20 C 1.0370(2) 0.64100(13) 0.66735(6) 0.0428(5) Uani 1 1 d . . . H20 H 1.1116 0.6785 0.6669 0.051 Uiso 1 1 calc R . . C21 C 1.04937(19) 0.56739(14) 0.69198(6) 0.0408(4) Uani 1 1 d . . . H21 H 1.1321 0.5547 0.7086 0.049 Uiso 1 1 calc R . . C22 C 0.94049(16) 0.51160(12) 0.69248(5) 0.0289(3) Uani 1 1 d . . . H22 H 0.9492 0.4607 0.7093 0.035 Uiso 1 1 calc R . . C23 C 0.71692(13) 0.37623(9) 0.70497(4) 0.0170(3) Uani 1 1 d . . . C24 C 0.79956(14) 0.30925(9) 0.69443(5) 0.0212(3) Uani 1 1 d . . . H24 H 0.8323 0.3101 0.6683 0.025 Uiso 1 1 calc R . . C25 C 0.83377(16) 0.24131(10) 0.72218(5) 0.0269(3) Uani 1 1 d . . . H25 H 0.8919 0.1966 0.7154 0.032 Uiso 1 1 calc R . . C26 C 0.78279(16) 0.23887(11) 0.75987(5) 0.0302(4) Uani 1 1 d . . . H26 H 0.8040 0.1916 0.7785 0.036 Uiso 1 1 calc R . . C27 C 0.70119(16) 0.30522(12) 0.77029(5) 0.0301(4) Uani 1 1 d . . . H27 H 0.6667 0.3034 0.7961 0.036 Uiso 1 1 calc R . . C28 C 0.66917(15) 0.37458(10) 0.74327(4) 0.0224(3) Uani 1 1 d . . . H28 H 0.6149 0.4207 0.7509 0.027 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 Se1 0.02449(8) 0.01735(7) 0.02091(8) -0.00041(5) 0.00764(5) 0.00357(5) P1 0.01767(16) 0.01434(16) 0.01344(15) -0.00093(12) 0.00372(12) -0.00115(12) N1 0.0158(5) 0.0149(5) 0.0167(5) -0.0006(4) 0.0018(4) -0.0022(4) N2 0.0164(5) 0.0175(5) 0.0133(5) 0.0004(4) 0.0023(4) -0.0019(4) B1 0.0128(6) 0.0187(7) 0.0171(7) -0.0014(6) 0.0012(5) 0.0002(5) C1 0.0132(6) 0.0169(6) 0.0167(6) -0.0012(5) 0.0014(5) -0.0012(5) C2 0.0151(6) 0.0176(6) 0.0154(6) -0.0010(5) 0.0019(5) -0.0005(5) C3 0.0190(6) 0.0170(6) 0.0201(7) -0.0009(5) 0.0035(5) -0.0035(5) C4 0.0226(7) 0.0231(7) 0.0208(7) -0.0057(5) 0.0023(5) -0.0056(6) C5 0.0226(7) 0.0280(8) 0.0151(6) -0.0029(5) 0.0015(5) -0.0031(6) C6 0.0187(6) 0.0216(7) 0.0176(6) 0.0012(5) 0.0036(5) -0.0007(5) C7 0.0255(7) 0.0175(6) 0.0202(7) 0.0015(5) 0.0005(5) -0.0052(6) C8 0.0273(8) 0.0338(9) 0.0306(8) 0.0042(7) 0.0055(6) -0.0137(7) C9 0.0188(6) 0.0188(6) 0.0159(6) 0.0032(5) 0.0016(5) -0.0009(5) C10 0.0196(7) 0.0283(8) 0.0210(7) 0.0041(6) 0.0027(5) -0.0044(6) C11 0.0176(6) 0.0152(6) 0.0157(6) 0.0009(5) 0.0013(5) 0.0001(5) C12 0.0166(6) 0.0195(6) 0.0168(6) -0.0016(5) 0.0038(5) -0.0002(5) C13 0.0158(6) 0.0196(6) 0.0172(6) -0.0015(5) 0.0021(5) -0.0021(5) C14 0.0193(6) 0.0153(6) 0.0138(6) -0.0002(5) 0.0024(5) -0.0006(5) C15 0.0178(6) 0.0197(6) 0.0172(6) -0.0004(5) 0.0051(5) -0.0009(5) C16 0.0161(6) 0.0190(7) 0.0182(6) 0.0000(5) 0.0012(5) -0.0023(5) C17 0.0237(7) 0.0207(7) 0.0149(6) -0.0054(5) 0.0067(5) -0.0064(5) C18 0.0363(8) 0.0254(8) 0.0201(7) -0.0017(6) 0.0084(6) -0.0087(7) C19 0.0534(11) 0.0318(9) 0.0256(8) -0.0029(7) 0.0145(8) -0.0210(8) C20 0.0470(11) 0.0498(12) 0.0337(9) -0.0114(8) 0.0128(8) -0.0328(9) C21 0.0319(9) 0.0539(12) 0.0351(9) -0.0073(9) -0.0001(7) -0.0201(9) C22 0.0268(8) 0.0335(8) 0.0257(8) -0.0017(6) 0.0004(6) -0.0100(7) C23 0.0175(6) 0.0172(6) 0.0159(6) 0.0002(5) 0.0013(5) -0.0020(5) C24 0.0209(7) 0.0214(7) 0.0210(7) -0.0027(5) 0.0021(5) 0.0005(5) C25 0.0252(7) 0.0217(7) 0.0311(8) -0.0027(6) -0.0056(6) 0.0050(6) C26 0.0302(8) 0.0277(8) 0.0298(8) 0.0103(7) -0.0064(6) 0.0012(7) C27 0.0291(8) 0.0398(9) 0.0212(7) 0.0104(7) 0.0028(6) 0.0019(7) C28 0.0212(7) 0.0276(8) 0.0189(7) 0.0037(6) 0.0042(5) 0.0027(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.1145(4) . ? P1 C23 1.8139(14) . ? P1 C17 1.8142(14) . ? P1 C14 1.8197(13) . ? N1 C1 1.3953(17) . ? N1 B1 1.4312(19) . ? N1 C7 1.4607(17) . ? N2 C2 1.3989(17) . ? N2 B1 1.4339(19) . ? N2 C9 1.4633(17) . ? B1 C11 1.570(2) . ? C1 C6 1.3885(19) . ? C1 C2 1.4100(18) . ? C2 C3 1.3869(19) . ? C3 C4 1.3954(19) . ? C3 H3 0.9500 . ? C4 C5 1.394(2) . ? C4 H4 0.9500 . ? C5 C6 1.396(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.519(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5275(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.4043(19) . ? C11 C12 1.4016(19) . ? C12 C13 1.3961(19) . ? C12 H12 0.9500 . ? C13 C14 1.4001(18) . ? C13 H13 0.9500 . ? C14 C15 1.3977(19) . ? C15 C16 1.3836(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.392(2) . ? C17 C18 1.398(2) . ? C18 C19 1.386(2) . ? C18 H18 0.9500 . ? C19 C20 1.384(3) . ? C19 H19 0.9500 . ? C20 C21 1.381(3) . ? C20 H20 0.9500 . ? C21 C22 1.396(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.3923(19) . ? C23 C24 1.398(2) . ? C24 C25 1.391(2) . ? C24 H24 0.9500 . ? C25 C26 1.390(2) . ? C25 H25 0.9500 . ? C26 C27 1.382(2) . ? C26 H26 0.9500 . ? C27 C28 1.390(2) . ? C27 H27 0.9500 . ? C28 H28 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 C23 P1 C17 106.68(7) . . ? C23 P1 C14 105.14(6) . . ? C17 P1 C14 106.83(6) . . ? C23 P1 Se1 113.53(5) . . ? C17 P1 Se1 112.56(5) . . ? C14 P1 Se1 111.57(5) . . ? C1 N1 B1 108.31(11) . . ? C1 N1 C7 121.05(11) . . ? B1 N1 C7 130.59(12) . . ? C2 N2 B1 108.14(11) . . ? C2 N2 C9 121.42(11) . . ? B1 N2 C9 130.43(12) . . ? N1 B1 N2 106.55(12) . . ? N1 B1 C11 127.53(13) . . ? N2 B1 C11 125.91(12) . . ? C6 C1 N1 130.75(13) . . ? C6 C1 C2 120.68(12) . . ? N1 C1 C2 108.56(11) . . ? C3 C2 N2 130.54(13) . . ? C3 C2 C1 121.02(12) . . ? N2 C2 C1 108.43(11) . . ? C2 C3 C4 118.12(13) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 120.90(13) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 121.17(13) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.09(13) . . ? C1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? N1 C7 C8 112.20(12) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 113.24(11) . . ? N2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 117.27(12) . . ? C16 C11 B1 119.92(12) . . ? C12 C11 B1 122.80(12) . . ? C13 C12 C11 121.75(12) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 119.62(12) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 119.39(12) . . ? C15 C14 P1 117.50(10) . . ? C13 C14 P1 123.07(10) . . ? C16 C15 C14 120.16(12) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 121.78(13) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? C22 C17 C18 119.70(14) . . ? C22 C17 P1 122.68(12) . . ? C18 C17 P1 117.52(12) . . ? C19 C18 C17 119.94(16) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.23(17) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.23(16) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C22 120.15(18) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 119.74(17) . . ? C17 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C28 C23 C24 119.76(13) . . ? C28 C23 P1 119.43(11) . . ? C24 C23 P1 120.81(11) . . ? C25 C24 C23 119.94(14) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C26 C25 C24 119.96(15) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 120.02(14) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.49(15) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 119.77(14) . . ? C27 C28 H28 120.1 . . ? C23 C28 H28 120.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.398 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.057 #============================================================================== data_compound6 _database_code_depnum_ccdc_archive 'CCDC 873272' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _vrf_CHEMW03_compound6 ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: highly disordered n-pentane was squeezed, but added in the sum formula for further calculations ; _vrf_PLAT043_compound6 ; PROBLEM: Check Reported Molecular Weight ................ 738.87 RESPONSE: highly disordered n-pentane was squeezed, but added in the sum formula for further calculations ; _vrf_PLAT044_compound6 ; PROBLEM: Calculated and Reported Dx Differ .............. ? RESPONSE: highly disordered n-pentane was squeezed, but added in the sum formula for further calculations ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.051 0.250 189.9 10.2 2 0.000 -0.086 0.750 189.9 10.4 3 0.500 -0.047 0.250 189.9 10.2 4 0.500 0.007 0.750 189.9 10.4 _platon_squeeze_details ; Der Kristall enth\"alt stark fehlgeordnetes n-Pentan. Da die so resultierende Restelektronendichte nicht sinnvoll verfeinert werden konnte, wurde die SQUEEZE-Routine des Programms PLATON (Spek, 2008) angewandt. Die angegebene Summenformel sowie die darauf basierenden Parameter ber\"ucksichtigen aber das fehlgeordnete L\"osungsmittel. Spek, A. L. (2008) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Au B Cl N2 P, (C5 H12 squeezed)' _chemical_formula_sum 'C33 H40 Au B Cl N2 P' _chemical_formula_weight 738.87 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' Au Au -2.0133 8.8022 '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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.195(7) _cell_length_b 9.7525(16) _cell_length_c 22.556(3) _cell_angle_alpha 90.00 _cell_angle_beta 128.270(17) _cell_angle_gamma 90.00 _cell_volume 5733.0(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 169 _cell_measurement_theta_min 3.449 _cell_measurement_theta_max 20.667 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 5.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5684 _exptl_absorpt_correction_T_max 0.8157 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26951 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6552 _reflns_number_gt 5205 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Disorder of C(7)/C(8) on two positions (61:39). Highly disordered n-pentane was squeezed see _platon_squeeze_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^)+(0.0210P)^2^+9.5926P] 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 6552 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Au1 Au 0.159377(5) -0.070083(15) 0.392950(8) 0.01792(5) Uani 1 1 d . . . Cl1 Cl 0.14919(4) -0.22450(11) 0.45950(6) 0.0301(2) Uani 1 1 d . . . P1 P 0.17230(3) 0.08405(10) 0.33354(5) 0.01460(19) Uani 1 1 d . . . N1 N -0.06439(12) 0.2131(4) -0.04229(17) 0.0312(8) Uani 1 1 d . . . N2 N 0.00013(10) 0.2849(3) -0.04464(15) 0.0154(6) Uani 1 1 d . . . B1 B -0.00994(17) 0.2296(5) 0.0033(2) 0.0227(10) Uani 1 1 d . A . C1 C -0.08652(14) 0.2576(4) -0.1155(2) 0.0219(9) Uani 1 1 d . A . C2 C -0.04651(13) 0.3004(4) -0.11667(19) 0.0166(8) Uani 1 1 d . A . C3 C -0.05706(14) 0.3469(4) -0.1834(2) 0.0196(8) Uani 1 1 d . . . H3 H -0.0303 0.3762 -0.1846 0.024 Uiso 1 1 calc R A . C4 C -0.10809(15) 0.3491(4) -0.2484(2) 0.0237(9) Uani 1 1 d . A . H4 H -0.1161 0.3794 -0.2947 0.028 Uiso 1 1 calc R . . C5 C -0.14716(15) 0.3079(4) -0.2466(2) 0.0261(9) Uani 1 1 d . . . H5 H -0.1817 0.3122 -0.2916 0.031 Uiso 1 1 calc R A . C6 C -0.13714(14) 0.2606(4) -0.1807(2) 0.0290(10) Uani 1 1 d . A . H6 H -0.1642 0.2311 -0.1802 0.035 Uiso 1 1 calc R . . C7A C -0.0955(3) 0.1878(8) -0.0191(4) 0.0206(18) Uiso 0.607(10) 1 d P A 1 H7A H -0.1249 0.2523 -0.0447 0.025 Uiso 0.607(10) 1 calc PR A 1 H7B H -0.0750 0.2002 0.0362 0.025 Uiso 0.607(10) 1 calc PR A 1 C8A C -0.1147(3) 0.0403(7) -0.0411(4) 0.030(2) Uiso 0.607(10) 1 d P A 1 H8A H -0.1365 0.0308 -0.0961 0.046 Uiso 0.607(10) 1 calc PR A 1 H8B H -0.1346 0.0174 -0.0237 0.046 Uiso 0.607(10) 1 calc PR A 1 H8C H -0.0853 -0.0219 -0.0176 0.046 Uiso 0.607(10) 1 calc PR A 1 C7B C -0.0958(4) 0.1142(12) -0.0274(6) 0.021(3) Uiso 0.393(10) 1 d P A 2 H7B1 H -0.1190 0.0541 -0.0716 0.025 Uiso 0.393(10) 1 calc PR A 2 H7B2 H -0.0719 0.0558 0.0174 0.025 Uiso 0.393(10) 1 calc PR A 2 C8B C -0.1257(4) 0.2038(11) -0.0144(6) 0.034(3) Uiso 0.393(10) 1 d P A 2 H8B1 H -0.1463 0.1472 -0.0064 0.051 Uiso 0.393(10) 1 calc PR A 2 H8B2 H -0.1484 0.2628 -0.0586 0.051 Uiso 0.393(10) 1 calc PR A 2 H8B3 H -0.1022 0.2609 0.0303 0.051 Uiso 0.393(10) 1 calc PR A 2 C9 C 0.04880(13) 0.3113(4) -0.0293(2) 0.0209(8) Uani 1 1 d . A . H9A H 0.0476 0.2728 -0.0709 0.025 Uiso 1 1 calc R . . H9B H 0.0763 0.2629 0.0177 0.025 Uiso 1 1 calc R . . C10 C 0.06247(17) 0.4633(4) -0.0207(3) 0.0381(12) Uani 1 1 d . . . H10A H 0.0349 0.5127 -0.0662 0.057 Uiso 1 1 calc R A . H10B H 0.0946 0.4741 -0.0136 0.057 Uiso 1 1 calc R . . H10C H 0.0667 0.5005 0.0232 0.057 Uiso 1 1 calc R . . C11 C 0.03209(14) 0.1957(4) 0.08921(19) 0.0206(8) Uani 1 1 d . . . C12 C 0.03881(14) 0.0637(4) 0.1182(2) 0.0223(8) Uani 1 1 d . A . H12 H 0.0148 -0.0059 0.0863 0.027 Uiso 1 1 calc R . . C13 C 0.07989(14) 0.0319(4) 0.1928(2) 0.0191(8) Uani 1 1 d . . . H13 H 0.0839 -0.0589 0.2111 0.023 Uiso 1 1 calc R A . C14 C 0.11517(13) 0.1335(4) 0.24064(19) 0.0167(8) Uani 1 1 d . A . C15 C 0.10782(14) 0.2684(4) 0.21407(19) 0.0194(8) Uani 1 1 d . . . H15 H 0.1305 0.3394 0.2468 0.023 Uiso 1 1 calc R A . C16 C 0.06675(14) 0.2968(4) 0.1390(2) 0.0219(8) Uani 1 1 d . A . H16 H 0.0622 0.3880 0.1210 0.026 Uiso 1 1 calc R . . C17 C 0.19665(13) 0.2468(4) 0.38316(18) 0.0157(8) Uani 1 1 d . . . C18 C 0.17231(14) 0.3023(4) 0.41053(19) 0.0225(9) Uani 1 1 d . . . H18 H 0.1478 0.2496 0.4095 0.027 Uiso 1 1 calc R . . C19 C 0.18389(15) 0.4336(4) 0.4391(2) 0.0271(9) Uani 1 1 d . . . H19 H 0.1667 0.4718 0.4567 0.033 Uiso 1 1 calc R . . C20 C 0.22021(15) 0.5104(4) 0.4423(2) 0.0240(9) Uani 1 1 d . . . H20 H 0.2277 0.6013 0.4616 0.029 Uiso 1 1 calc R . . C21 C 0.24562(15) 0.4544(4) 0.4175(2) 0.0236(9) Uani 1 1 d . . . H21 H 0.2712 0.5062 0.4208 0.028 Uiso 1 1 calc R . . C22 C 0.23389(14) 0.3226(4) 0.38760(19) 0.0199(8) Uani 1 1 d . . . H22 H 0.2513 0.2845 0.3703 0.024 Uiso 1 1 calc R . . C23 C 0.21712(13) 0.0269(4) 0.3176(2) 0.0161(8) Uani 1 1 d . . . C24 C 0.25560(14) -0.0653(4) 0.3675(2) 0.0209(8) Uani 1 1 d . . . H24 H 0.2576 -0.1002 0.4085 0.025 Uiso 1 1 calc R . . C25 C 0.29108(15) -0.1069(4) 0.3579(2) 0.0263(9) Uani 1 1 d . . . H25 H 0.3170 -0.1711 0.3918 0.032 Uiso 1 1 calc R . . C26 C 0.28854(16) -0.0541(4) 0.2985(2) 0.0281(9) Uani 1 1 d . . . H26 H 0.3134 -0.0805 0.2925 0.034 Uiso 1 1 calc R . . C27 C 0.25028(16) 0.0360(4) 0.2483(2) 0.0266(9) Uani 1 1 d . . . H27 H 0.2484 0.0704 0.2072 0.032 Uiso 1 1 calc R . . C28 C 0.21433(15) 0.0771(4) 0.2572(2) 0.0219(8) Uani 1 1 d . . . H28 H 0.1879 0.1393 0.2223 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 Au1 0.01704(8) 0.02244(8) 0.01729(7) 0.00227(7) 0.01213(6) 0.00003(7) Cl1 0.0324(6) 0.0334(6) 0.0340(5) 0.0111(5) 0.0253(5) 0.0013(5) P1 0.0128(4) 0.0185(5) 0.0124(4) -0.0009(4) 0.0078(4) -0.0012(4) N1 0.0149(17) 0.061(2) 0.0155(16) 0.0050(18) 0.0083(14) -0.0021(18) N2 0.0107(15) 0.0166(16) 0.0153(14) -0.0026(13) 0.0062(13) -0.0005(13) B1 0.019(2) 0.027(3) 0.021(2) -0.006(2) 0.012(2) 0.003(2) C1 0.017(2) 0.032(2) 0.0149(18) -0.0015(17) 0.0085(17) 0.0006(18) C2 0.0152(19) 0.0152(19) 0.0140(17) -0.0035(16) 0.0064(16) -0.0014(16) C3 0.020(2) 0.0149(19) 0.024(2) 0.0030(17) 0.0132(18) 0.0030(17) C4 0.029(2) 0.017(2) 0.0173(19) 0.0005(17) 0.0105(19) 0.0012(18) C5 0.018(2) 0.030(2) 0.0163(19) 0.0017(18) 0.0039(18) 0.0018(19) C6 0.013(2) 0.047(3) 0.022(2) 0.002(2) 0.0075(18) 0.0003(19) C9 0.0126(19) 0.022(2) 0.025(2) 0.0046(17) 0.0098(17) 0.0015(17) C10 0.028(2) 0.019(2) 0.050(3) 0.008(2) 0.016(2) -0.0040(19) C11 0.016(2) 0.030(2) 0.0151(18) 0.0007(17) 0.0096(17) 0.0006(18) C12 0.0149(18) 0.030(2) 0.0165(18) -0.0079(19) 0.0069(16) -0.0088(19) C13 0.018(2) 0.020(2) 0.0173(19) 0.0010(16) 0.0100(17) -0.0025(16) C14 0.0148(19) 0.021(2) 0.0146(17) -0.0007(16) 0.0091(16) 0.0011(17) C15 0.0169(19) 0.022(2) 0.0160(18) -0.0037(17) 0.0087(17) 0.0002(17) C16 0.022(2) 0.021(2) 0.0202(19) 0.0029(17) 0.0119(18) 0.0070(18) C17 0.0157(19) 0.016(2) 0.0074(16) -0.0019(15) 0.0034(15) 0.0012(16) C18 0.018(2) 0.031(2) 0.0168(19) -0.0036(18) 0.0101(17) -0.0023(18) C19 0.026(2) 0.034(2) 0.0175(19) -0.002(2) 0.0118(18) 0.007(2) C20 0.028(2) 0.019(2) 0.0126(18) 0.0013(17) 0.0063(18) 0.0065(19) C21 0.022(2) 0.026(2) 0.0131(18) 0.0034(17) 0.0064(17) -0.0021(18) C22 0.018(2) 0.026(2) 0.0138(18) -0.0028(17) 0.0091(17) -0.0020(17) C23 0.0122(18) 0.0171(19) 0.0170(18) -0.0039(15) 0.0080(16) -0.0053(16) C24 0.0202(19) 0.024(2) 0.0205(18) -0.0074(18) 0.0137(17) -0.0042(19) C25 0.021(2) 0.026(2) 0.031(2) -0.0014(18) 0.0156(19) 0.0040(18) C26 0.032(2) 0.027(2) 0.040(2) -0.006(2) 0.029(2) -0.001(2) C27 0.035(2) 0.027(2) 0.029(2) 0.0017(18) 0.025(2) 0.0004(19) C28 0.026(2) 0.023(2) 0.0207(18) -0.0012(18) 0.0162(18) -0.0039(19) _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 Au1 P1 2.2252(9) . ? Au1 Cl1 2.2945(10) . ? P1 C14 1.816(4) . ? P1 C17 1.818(4) . ? P1 C23 1.822(4) . ? N1 C1 1.398(4) . ? N1 B1 1.431(5) . ? N1 C7A 1.440(7) . ? N1 C7B 1.601(11) . ? N2 C2 1.394(4) . ? N2 B1 1.421(5) . ? N2 C9 1.450(4) . ? B1 C11 1.570(5) . ? C1 C6 1.388(5) . ? C1 C2 1.408(5) . ? C2 C3 1.394(5) . ? C3 C4 1.394(5) . ? C3 H3 0.9500 . ? C4 C5 1.382(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7A C8A 1.526(10) . ? C7A H7A 0.9900 . ? C7A H7B 0.9900 . ? C8A H8A 0.9800 . ? C8A H8B 0.9800 . ? C8A H8C 0.9800 . ? C7B C8B 1.482(15) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 0.9800 . ? C9 C10 1.526(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.397(5) . ? C11 C16 1.399(5) . ? C12 C13 1.395(5) . ? C12 H12 0.9500 . ? C13 C14 1.397(5) . ? C13 H13 0.9500 . ? C14 C15 1.403(5) . ? C15 C16 1.394(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.390(5) . ? C17 C18 1.394(5) . ? C18 C19 1.377(5) . ? C18 H18 0.9500 . ? C19 C20 1.382(6) . ? C19 H19 0.9500 . ? C20 C21 1.382(5) . ? C20 H20 0.9500 . ? C21 C22 1.390(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.388(5) . ? C23 C28 1.395(5) . ? C24 C25 1.383(5) . ? C24 H24 0.9500 . ? C25 C26 1.388(5) . ? C25 H25 0.9500 . ? C26 C27 1.374(6) . ? C26 H26 0.9500 . ? C27 C28 1.386(5) . ? C27 H27 0.9500 . ? C28 H28 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 P1 Au1 Cl1 177.30(4) . . ? C14 P1 C17 103.11(16) . . ? C14 P1 C23 104.49(16) . . ? C17 P1 C23 106.42(17) . . ? C14 P1 Au1 114.90(12) . . ? C17 P1 Au1 113.40(12) . . ? C23 P1 Au1 113.48(12) . . ? C1 N1 B1 108.6(3) . . ? C1 N1 C7A 120.8(4) . . ? B1 N1 C7A 129.1(4) . . ? C1 N1 C7B 120.1(5) . . ? B1 N1 C7B 127.9(5) . . ? C7A N1 C7B 27.6(4) . . ? C2 N2 B1 108.2(3) . . ? C2 N2 C9 121.9(3) . . ? B1 N2 C9 129.6(3) . . ? N2 B1 N1 106.5(3) . . ? N2 B1 C11 124.9(3) . . ? N1 B1 C11 128.6(4) . . ? C6 C1 N1 131.6(4) . . ? C6 C1 C2 120.7(3) . . ? N1 C1 C2 107.6(3) . . ? C3 C2 N2 130.5(3) . . ? C3 C2 C1 120.5(3) . . ? N2 C2 C1 109.0(3) . . ? C2 C3 C4 118.0(4) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 121.5(4) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.2(4) . . ? C5 C6 H6 120.9 . . ? C1 C6 H6 120.9 . . ? N1 C7A C8A 106.9(6) . . ? N1 C7A H7A 110.3 . . ? C8A C7A H7A 110.3 . . ? N1 C7A H7B 110.3 . . ? C8A C7A H7B 110.3 . . ? H7A C7A H7B 108.6 . . ? C8B C7B N1 106.8(9) . . ? C8B C7B H7B1 110.4 . . ? N1 C7B H7B1 110.4 . . ? C8B C7B H7B2 110.4 . . ? N1 C7B H7B2 110.4 . . ? H7B1 C7B H7B2 108.6 . . ? C7B C8B H8B1 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C7B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? N2 C9 C10 113.7(3) . . ? N2 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N2 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 117.4(3) . . ? C12 C11 B1 122.3(3) . . ? C16 C11 B1 120.2(3) . . ? C13 C12 C11 121.5(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 P1 118.7(3) . . ? C15 C14 P1 121.5(3) . . ? C16 C15 C14 119.1(3) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 122.3(4) . . ? C15 C16 H16 118.8 . . ? C11 C16 H16 118.8 . . ? C22 C17 C18 119.7(3) . . ? C22 C17 P1 123.0(3) . . ? C18 C17 P1 116.9(3) . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.7(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C21 119.7(4) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 120.2(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 119.8(3) . . ? C17 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C28 119.4(3) . . ? C24 C23 P1 119.4(3) . . ? C28 C23 P1 121.2(3) . . ? C25 C24 C23 120.5(4) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 119.6(4) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 120.4(4) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C28 120.3(4) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 119.8(4) . . ? C27 C28 H28 120.1 . . ? C23 C28 H28 120.1 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.837 _refine_diff_density_min -0.843 _refine_diff_density_rms 0.131 #============================================================================== data_compound7 _database_code_depnum_ccdc_archive 'CCDC 873273' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H31 B N2 P, C H3 O4 S' _chemical_formula_sum 'C30 H34 B N2 O4 P S' _chemical_formula_weight 560.43 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' S S 0.1246 0.1234 '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 19.6129(3) _cell_length_b 8.41430(10) _cell_length_c 18.1021(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.7219(7) _cell_angle_gamma 90.00 _cell_volume 2794.11(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 45603 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9390 _exptl_absorpt_correction_T_max 0.9668 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 75053 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8133 _reflns_number_gt 6417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.6918P] 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 8133 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 P1 P 0.810759(16) 0.41314(4) 0.011684(17) 0.01478(7) Uani 1 1 d . . . N1 N 0.48045(5) 0.80114(12) -0.00341(5) 0.01492(19) Uani 1 1 d . . . N2 N 0.53904(5) 0.75336(12) 0.12932(6) 0.01569(19) Uani 1 1 d . . . B1 B 0.54686(7) 0.74148(15) 0.05338(8) 0.0156(2) Uani 1 1 d . . . C1 C 0.43467(6) 0.84874(14) 0.03672(7) 0.0154(2) Uani 1 1 d . . . C2 C 0.47046(6) 0.81756(14) 0.11802(7) 0.0158(2) Uani 1 1 d . . . C3 C 0.43687(7) 0.85127(15) 0.17221(7) 0.0187(2) Uani 1 1 d . . . H3 H 0.4604 0.8278 0.2267 0.022 Uiso 1 1 calc R . . C4 C 0.36781(7) 0.92049(15) 0.14446(7) 0.0210(2) Uani 1 1 d . . . H4 H 0.3437 0.9434 0.1804 0.025 Uiso 1 1 calc R . . C5 C 0.33367(7) 0.95649(15) 0.06458(8) 0.0209(2) Uani 1 1 d . . . H5 H 0.2874 1.0070 0.0473 0.025 Uiso 1 1 calc R . . C6 C 0.36646(6) 0.91953(14) 0.00956(7) 0.0180(2) Uani 1 1 d . . . H6 H 0.3426 0.9423 -0.0449 0.022 Uiso 1 1 calc R . . C7 C 0.45871(6) 0.82380(14) -0.08871(7) 0.0168(2) Uani 1 1 d . . . H7A H 0.5024 0.8162 -0.1038 0.020 Uiso 1 1 calc R . . H7B H 0.4381 0.9318 -0.1025 0.020 Uiso 1 1 calc R . . C8 C 0.40253(7) 0.70219(15) -0.13601(7) 0.0203(2) Uani 1 1 d . . . H8A H 0.4251 0.5967 -0.1293 0.031 Uiso 1 1 calc R . . H8B H 0.3849 0.7313 -0.1920 0.031 Uiso 1 1 calc R . . H8C H 0.3615 0.7004 -0.1171 0.031 Uiso 1 1 calc R . . C9 C 0.58992(7) 0.71668(15) 0.20876(7) 0.0194(2) Uani 1 1 d . . . H9A H 0.6289 0.6465 0.2045 0.023 Uiso 1 1 calc R . . H9B H 0.5636 0.6578 0.2378 0.023 Uiso 1 1 calc R . . C10 C 0.62473(7) 0.86481(18) 0.25587(8) 0.0266(3) Uani 1 1 d . . . H10A H 0.6535 0.9201 0.2292 0.040 Uiso 1 1 calc R . . H10B H 0.6566 0.8336 0.3090 0.040 Uiso 1 1 calc R . . H10C H 0.5865 0.9357 0.2596 0.040 Uiso 1 1 calc R . . C11 C 0.61404(6) 0.67167(14) 0.03681(7) 0.0156(2) Uani 1 1 d . . . C12 C 0.60510(6) 0.56656(14) -0.02609(7) 0.0162(2) Uani 1 1 d . . . H12 H 0.5574 0.5451 -0.0621 0.019 Uiso 1 1 calc R . . C13 C 0.66431(6) 0.49288(14) -0.03709(7) 0.0161(2) Uani 1 1 d . . . H13 H 0.6570 0.4203 -0.0794 0.019 Uiso 1 1 calc R . . C14 C 0.73473(6) 0.52698(14) 0.01488(7) 0.0155(2) Uani 1 1 d . . . C15 C 0.74514(6) 0.63437(14) 0.07673(7) 0.0172(2) Uani 1 1 d . . . H15 H 0.7930 0.6589 0.1114 0.021 Uiso 1 1 calc R . . C16 C 0.68553(6) 0.70494(14) 0.08735(7) 0.0176(2) Uani 1 1 d . . . H16 H 0.6931 0.7775 0.1297 0.021 Uiso 1 1 calc R . . C17 C 0.82078(6) 0.24612(14) 0.07661(7) 0.0162(2) Uani 1 1 d . . . C18 C 0.85121(7) 0.10260(15) 0.06380(7) 0.0191(2) Uani 1 1 d . . . H18 H 0.8678 0.0920 0.0207 0.023 Uiso 1 1 calc R . . C19 C 0.85680(7) -0.02416(15) 0.11504(8) 0.0226(3) Uani 1 1 d . . . H19 H 0.8777 -0.1215 0.1069 0.027 Uiso 1 1 calc R . . C20 C 0.83214(7) -0.00969(16) 0.17808(7) 0.0224(3) Uani 1 1 d . . . H20 H 0.8350 -0.0978 0.2119 0.027 Uiso 1 1 calc R . . C21 C 0.80340(7) 0.13354(16) 0.19139(7) 0.0219(3) Uani 1 1 d . . . H21 H 0.7876 0.1440 0.2351 0.026 Uiso 1 1 calc R . . C22 C 0.79764(7) 0.26192(15) 0.14119(7) 0.0191(2) Uani 1 1 d . . . H22 H 0.7781 0.3599 0.1506 0.023 Uiso 1 1 calc R . . C23 C 0.89248(6) 0.53100(15) 0.04640(7) 0.0177(2) Uani 1 1 d . . . C24 C 0.90206(7) 0.65365(16) -0.00121(8) 0.0238(3) Uani 1 1 d . . . H24 H 0.8662 0.6729 -0.0517 0.029 Uiso 1 1 calc R . . C25 C 0.96451(8) 0.74708(17) 0.02603(9) 0.0277(3) Uani 1 1 d . . . H25 H 0.9712 0.8307 -0.0060 0.033 Uiso 1 1 calc R . . C26 C 1.01707(7) 0.71922(17) 0.09949(9) 0.0270(3) Uani 1 1 d . . . H26 H 1.0596 0.7836 0.1177 0.032 Uiso 1 1 calc R . . C27 C 1.00752(7) 0.59721(18) 0.14641(9) 0.0292(3) Uani 1 1 d . . . H27 H 1.0438 0.5778 0.1967 0.035 Uiso 1 1 calc R . . C28 C 0.94513(7) 0.50281(17) 0.12038(8) 0.0251(3) Uani 1 1 d . . . H28 H 0.9386 0.4199 0.1529 0.030 Uiso 1 1 calc R . . C29 C 0.79515(7) 0.35088(16) -0.08770(7) 0.0203(2) Uani 1 1 d . . . H29A H 0.7916 0.4445 -0.1211 0.030 Uiso 1 1 calc R . . H29B H 0.7496 0.2902 -0.1077 0.030 Uiso 1 1 calc R . . H29C H 0.8357 0.2839 -0.0886 0.030 Uiso 1 1 calc R . . S1 S 0.183192(16) 0.08009(4) 0.185928(17) 0.01886(8) Uani 1 1 d . . . O1 O 0.14321(5) 0.01015(11) 0.10969(5) 0.0254(2) Uani 1 1 d . . . O2 O 0.20135(6) 0.24551(12) 0.18116(6) 0.0298(2) Uani 1 1 d . . . O3 O 0.24171(5) -0.01591(13) 0.23671(6) 0.0280(2) Uani 1 1 d . . . O4 O 0.12631(5) 0.08087(13) 0.23284(5) 0.0277(2) Uani 1 1 d . . . C30 C 0.05792(8) 0.1567(2) 0.19089(9) 0.0342(3) Uani 1 1 d . . . H30A H 0.0667 0.2557 0.1672 0.051 Uiso 1 1 calc R . . H30B H 0.0327 0.1804 0.2276 0.051 Uiso 1 1 calc R . . H30C H 0.0277 0.0856 0.1492 0.051 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 0.01416(14) 0.01603(15) 0.01484(14) 0.00048(11) 0.00597(11) 0.00147(11) N1 0.0153(5) 0.0151(5) 0.0149(4) -0.0003(4) 0.0060(4) 0.0005(4) N2 0.0156(5) 0.0156(5) 0.0156(5) 0.0001(4) 0.0052(4) 0.0018(4) B1 0.0171(6) 0.0127(6) 0.0169(6) -0.0012(5) 0.0059(5) -0.0011(5) C1 0.0173(5) 0.0126(5) 0.0173(5) -0.0024(4) 0.0074(4) -0.0015(4) C2 0.0159(5) 0.0136(5) 0.0183(5) -0.0011(4) 0.0065(4) -0.0005(4) C3 0.0202(6) 0.0203(6) 0.0163(5) -0.0032(4) 0.0073(4) -0.0019(5) C4 0.0191(6) 0.0231(6) 0.0233(6) -0.0078(5) 0.0106(5) -0.0026(5) C5 0.0150(5) 0.0203(6) 0.0264(6) -0.0058(5) 0.0061(5) 0.0010(5) C6 0.0170(6) 0.0166(6) 0.0184(5) -0.0020(4) 0.0039(4) -0.0010(4) C7 0.0195(6) 0.0168(5) 0.0143(5) 0.0010(4) 0.0062(4) -0.0003(4) C8 0.0222(6) 0.0214(6) 0.0162(5) -0.0028(5) 0.0053(5) -0.0019(5) C9 0.0196(6) 0.0220(6) 0.0153(5) 0.0019(4) 0.0046(4) 0.0035(5) C10 0.0235(6) 0.0327(7) 0.0194(6) -0.0061(5) 0.0022(5) 0.0037(6) C11 0.0176(5) 0.0139(5) 0.0162(5) 0.0021(4) 0.0069(4) 0.0010(4) C12 0.0154(5) 0.0171(5) 0.0161(5) 0.0004(4) 0.0053(4) -0.0003(4) C13 0.0177(5) 0.0163(5) 0.0147(5) -0.0004(4) 0.0061(4) 0.0002(4) C14 0.0162(5) 0.0152(5) 0.0162(5) 0.0019(4) 0.0071(4) 0.0017(4) C15 0.0161(5) 0.0164(5) 0.0183(5) -0.0010(4) 0.0050(4) -0.0001(4) C16 0.0191(6) 0.0161(5) 0.0178(5) -0.0027(4) 0.0069(4) -0.0001(4) C17 0.0138(5) 0.0172(5) 0.0163(5) 0.0008(4) 0.0039(4) -0.0002(4) C18 0.0181(6) 0.0187(6) 0.0200(6) -0.0014(4) 0.0063(5) 0.0004(4) C19 0.0224(6) 0.0161(6) 0.0265(6) -0.0009(5) 0.0051(5) 0.0012(5) C20 0.0218(6) 0.0199(6) 0.0206(6) 0.0045(5) 0.0014(5) -0.0035(5) C21 0.0222(6) 0.0254(6) 0.0172(6) 0.0019(5) 0.0059(5) -0.0017(5) C22 0.0199(6) 0.0192(6) 0.0183(6) 0.0001(4) 0.0068(5) 0.0012(5) C23 0.0154(5) 0.0182(6) 0.0210(6) 0.0000(4) 0.0085(4) 0.0014(4) C24 0.0251(6) 0.0237(6) 0.0233(6) 0.0025(5) 0.0095(5) -0.0014(5) C25 0.0303(7) 0.0243(7) 0.0332(7) 0.0025(6) 0.0171(6) -0.0034(6) C26 0.0173(6) 0.0261(7) 0.0406(8) -0.0046(6) 0.0139(6) -0.0030(5) C27 0.0176(6) 0.0326(8) 0.0320(7) 0.0021(6) 0.0019(5) -0.0001(6) C28 0.0198(6) 0.0263(7) 0.0263(6) 0.0054(5) 0.0046(5) -0.0002(5) C29 0.0205(6) 0.0246(6) 0.0171(5) -0.0007(5) 0.0082(5) 0.0028(5) S1 0.01865(15) 0.02052(15) 0.01827(14) -0.00011(11) 0.00759(11) 0.00052(11) O1 0.0300(5) 0.0238(5) 0.0221(4) -0.0045(4) 0.0087(4) -0.0002(4) O2 0.0299(5) 0.0240(5) 0.0322(5) -0.0016(4) 0.0070(4) -0.0053(4) O3 0.0227(5) 0.0366(6) 0.0268(5) 0.0089(4) 0.0114(4) 0.0075(4) O4 0.0223(5) 0.0403(6) 0.0236(5) 0.0037(4) 0.0118(4) 0.0071(4) C30 0.0237(7) 0.0473(9) 0.0323(7) -0.0003(7) 0.0109(6) 0.0111(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C14 1.7904(12) . ? P1 C29 1.7931(12) . ? P1 C17 1.7977(12) . ? P1 C23 1.7984(12) . ? N1 C1 1.3986(14) . ? N1 B1 1.4344(16) . ? N1 C7 1.4616(14) . ? N2 C2 1.3957(15) . ? N2 B1 1.4395(16) . ? N2 C9 1.4642(15) . ? B1 C11 1.5655(17) . ? C1 C6 1.3860(16) . ? C1 C2 1.4129(16) . ? C2 C3 1.3907(16) . ? C3 C4 1.3946(18) . ? C3 H3 0.9500 . ? C4 C5 1.3949(18) . ? C4 H4 0.9500 . ? C5 C6 1.3983(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5253(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5280(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.4029(16) . ? C11 C16 1.4049(17) . ? C12 C13 1.3914(16) . ? C12 H12 0.9500 . ? C13 C14 1.3984(16) . ? C13 H13 0.9500 . ? C14 C15 1.3965(16) . ? C15 C16 1.3839(16) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.4021(16) . ? C17 C18 1.4022(17) . ? C18 C19 1.3921(18) . ? C18 H18 0.9500 . ? C19 C20 1.3934(19) . ? C19 H19 0.9500 . ? C20 C21 1.3873(19) . ? C20 H20 0.9500 . ? C21 C22 1.3902(18) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.3919(18) . ? C23 C24 1.3992(18) . ? C24 C25 1.3907(19) . ? C24 H24 0.9500 . ? C25 C26 1.384(2) . ? C25 H25 0.9500 . ? C26 C27 1.387(2) . ? C26 H26 0.9500 . ? C27 C28 1.3936(19) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? S1 O3 1.4382(10) . ? S1 O2 1.4468(10) . ? S1 O1 1.4491(9) . ? S1 O4 1.6237(9) . ? O4 C30 1.4358(17) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 C14 P1 C29 109.89(6) . . ? C14 P1 C17 107.27(5) . . ? C29 P1 C17 111.59(6) . . ? C14 P1 C23 110.07(6) . . ? C29 P1 C23 109.05(6) . . ? C17 P1 C23 108.95(5) . . ? C1 N1 B1 108.35(9) . . ? C1 N1 C7 120.69(10) . . ? B1 N1 C7 130.87(10) . . ? C2 N2 B1 108.04(9) . . ? C2 N2 C9 120.81(9) . . ? B1 N2 C9 131.10(10) . . ? N1 B1 N2 106.48(10) . . ? N1 B1 C11 127.31(10) . . ? N2 B1 C11 126.18(11) . . ? C6 C1 N1 130.95(11) . . ? C6 C1 C2 120.71(10) . . ? N1 C1 C2 108.32(10) . . ? C3 C2 N2 130.39(11) . . ? C3 C2 C1 120.80(11) . . ? N2 C2 C1 108.80(10) . . ? C2 C3 C4 118.24(11) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 C5 120.86(11) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 121.13(11) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.19(11) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? N1 C7 C8 112.85(10) . . ? N1 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 113.01(10) . . ? N2 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 117.61(11) . . ? C12 C11 B1 121.34(10) . . ? C16 C11 B1 120.95(10) . . ? C13 C12 C11 121.74(11) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 119.21(11) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.11(11) . . ? C15 C14 P1 119.00(9) . . ? C13 C14 P1 120.28(9) . . ? C16 C15 C14 119.86(11) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 121.44(11) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C22 C17 C18 120.12(11) . . ? C22 C17 P1 118.57(9) . . ? C18 C17 P1 121.31(9) . . ? C19 C18 C17 119.18(11) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.69(12) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 119.89(12) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.36(12) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 119.74(11) . . ? C21 C22 H22 120.1 . . ? C17 C22 H22 120.1 . . ? C28 C23 C24 120.18(12) . . ? C28 C23 P1 120.55(10) . . ? C24 C23 P1 119.26(9) . . ? C25 C24 C23 119.47(12) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C26 C25 C24 120.53(13) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 119.85(13) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 120.50(13) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C23 C28 C27 119.47(12) . . ? C23 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? P1 C29 H29A 109.5 . . ? P1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? P1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O3 S1 O2 114.89(6) . . ? O3 S1 O1 114.91(6) . . ? O2 S1 O1 113.30(6) . . ? O3 S1 O4 102.04(5) . . ? O2 S1 O4 104.86(6) . . ? O1 S1 O4 105.03(5) . . ? C30 O4 S1 114.29(9) . . ? O4 C30 H30A 109.5 . . ? O4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 C1 N1 B1 N2 0.60(13) . . . . ? C7 N1 B1 N2 177.17(11) . . . . ? C1 N1 B1 C11 178.79(11) . . . . ? C7 N1 B1 C11 -4.6(2) . . . . ? C2 N2 B1 N1 0.07(13) . . . . ? C9 N2 B1 N1 -177.21(11) . . . . ? C2 N2 B1 C11 -178.14(11) . . . . ? C9 N2 B1 C11 4.6(2) . . . . ? B1 N1 C1 C6 177.06(12) . . . . ? C7 N1 C1 C6 0.07(19) . . . . ? B1 N1 C1 C2 -1.04(13) . . . . ? C7 N1 C1 C2 -178.03(10) . . . . ? B1 N2 C2 C3 179.47(12) . . . . ? C9 N2 C2 C3 -2.92(19) . . . . ? B1 N2 C2 C1 -0.71(13) . . . . ? C9 N2 C2 C1 176.91(10) . . . . ? C6 C1 C2 C3 2.60(18) . . . . ? N1 C1 C2 C3 -179.06(11) . . . . ? C6 C1 C2 N2 -177.24(10) . . . . ? N1 C1 C2 N2 1.09(13) . . . . ? N2 C2 C3 C4 178.13(12) . . . . ? C1 C2 C3 C4 -1.68(18) . . . . ? C2 C3 C4 C5 -0.67(19) . . . . ? C3 C4 C5 C6 2.2(2) . . . . ? N1 C1 C6 C5 -179.00(12) . . . . ? C2 C1 C6 C5 -1.10(17) . . . . ? C4 C5 C6 C1 -1.25(18) . . . . ? C1 N1 C7 C8 -76.61(14) . . . . ? B1 N1 C7 C8 107.18(14) . . . . ? C2 N2 C9 C10 -74.07(14) . . . . ? B1 N2 C9 C10 102.92(14) . . . . ? N1 B1 C11 C12 -42.92(18) . . . . ? N2 B1 C11 C12 134.92(13) . . . . ? N1 B1 C11 C16 140.87(12) . . . . ? N2 B1 C11 C16 -41.29(18) . . . . ? C16 C11 C12 C13 2.18(17) . . . . ? B1 C11 C12 C13 -174.15(11) . . . . ? C11 C12 C13 C14 -1.40(17) . . . . ? C12 C13 C14 C15 -0.29(17) . . . . ? C12 C13 C14 P1 170.64(9) . . . . ? C29 P1 C14 C15 -156.33(9) . . . . ? C17 P1 C14 C15 82.20(10) . . . . ? C23 P1 C14 C15 -36.21(11) . . . . ? C29 P1 C14 C13 32.64(11) . . . . ? C17 P1 C14 C13 -88.84(10) . . . . ? C23 P1 C14 C13 152.76(9) . . . . ? C13 C14 C15 C16 1.12(18) . . . . ? P1 C14 C15 C16 -169.92(9) . . . . ? C14 C15 C16 C11 -0.30(18) . . . . ? C12 C11 C16 C15 -1.32(17) . . . . ? B1 C11 C16 C15 175.03(11) . . . . ? C14 P1 C17 C22 -28.27(11) . . . . ? C29 P1 C17 C22 -148.67(9) . . . . ? C23 P1 C17 C22 90.86(10) . . . . ? C14 P1 C17 C18 151.93(10) . . . . ? C29 P1 C17 C18 31.53(12) . . . . ? C23 P1 C17 C18 -88.94(11) . . . . ? C22 C17 C18 C19 1.18(18) . . . . ? P1 C17 C18 C19 -179.03(9) . . . . ? C17 C18 C19 C20 0.41(19) . . . . ? C18 C19 C20 C21 -1.68(19) . . . . ? C19 C20 C21 C22 1.34(19) . . . . ? C20 C21 C22 C17 0.24(19) . . . . ? C18 C17 C22 C21 -1.51(18) . . . . ? P1 C17 C22 C21 178.69(9) . . . . ? C14 P1 C23 C28 106.41(11) . . . . ? C29 P1 C23 C28 -132.97(11) . . . . ? C17 P1 C23 C28 -10.95(12) . . . . ? C14 P1 C23 C24 -72.42(11) . . . . ? C29 P1 C23 C24 48.20(12) . . . . ? C17 P1 C23 C24 170.22(10) . . . . ? C28 C23 C24 C25 -0.08(19) . . . . ? P1 C23 C24 C25 178.76(10) . . . . ? C23 C24 C25 C26 0.2(2) . . . . ? C24 C25 C26 C27 0.0(2) . . . . ? C25 C26 C27 C28 -0.4(2) . . . . ? C24 C23 C28 C27 -0.3(2) . . . . ? P1 C23 C28 C27 -179.11(11) . . . . ? C26 C27 C28 C23 0.5(2) . . . . ? O3 S1 O4 C30 -174.04(10) . . . . ? O2 S1 O4 C30 65.84(11) . . . . ? O1 S1 O4 C30 -53.83(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.388 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.053 #============================================================================== data_compound8 _database_code_depnum_ccdc_archive 'CCDC 873274' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 B N2 P S' _chemical_formula_sum 'C26 H26 B N2 P S' _chemical_formula_weight 440.33 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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7717(3) _cell_length_b 10.1929(4) _cell_length_c 13.9611(5) _cell_angle_alpha 102.719(3) _cell_angle_beta 91.738(2) _cell_angle_gamma 109.672(2) _cell_volume 1139.12(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 49031 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9408 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29176 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6632 _reflns_number_gt 5216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3365P] 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 6632 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 P1 P 0.63215(4) 0.25423(4) 1.10917(2) 0.01958(9) Uani 1 1 d . . . S1 S 0.48876(4) 0.20317(4) 0.89384(2) 0.02111(9) Uani 1 1 d . . . N2 N 0.55804(14) 0.29222(12) 0.62725(8) 0.0198(2) Uani 1 1 d . . . N1 N 0.39972(13) 0.06457(12) 0.63535(8) 0.0197(2) Uani 1 1 d . . . B1 B 0.52429(18) 0.19458(17) 0.68997(11) 0.0200(3) Uani 1 1 d . . . C1 C 0.36060(16) 0.08405(15) 0.54327(10) 0.0196(3) Uani 1 1 d . . . C2 C 0.45581(16) 0.22445(15) 0.53867(10) 0.0195(3) Uani 1 1 d . . . C3 C 0.43743(17) 0.27566(15) 0.45654(10) 0.0216(3) Uani 1 1 d . . . H3 H 0.5002 0.3711 0.4545 0.026 Uiso 1 1 calc R . . C4 C 0.32445(17) 0.18343(16) 0.37696(10) 0.0245(3) Uani 1 1 d . . . H4 H 0.3091 0.2166 0.3202 0.029 Uiso 1 1 calc R . . C5 C 0.23389(17) 0.04316(16) 0.37994(10) 0.0243(3) Uani 1 1 d . . . H5 H 0.1600 -0.0188 0.3242 0.029 Uiso 1 1 calc R . . C6 C 0.24926(17) -0.00859(15) 0.46319(10) 0.0225(3) Uani 1 1 d . . . H6 H 0.1858 -0.1039 0.4651 0.027 Uiso 1 1 calc R . . C7 C 0.32827(17) -0.07291(15) 0.66125(10) 0.0223(3) Uani 1 1 d . . . H7A H 0.3979 -0.0750 0.7176 0.027 Uiso 1 1 calc R . . H7B H 0.3272 -0.1512 0.6045 0.027 Uiso 1 1 calc R . . C8 C 0.15588(18) -0.10102(17) 0.68872(12) 0.0285(3) Uani 1 1 d . . . H8A H 0.1566 -0.0269 0.7471 0.043 Uiso 1 1 calc R . . H8B H 0.1136 -0.1957 0.7034 0.043 Uiso 1 1 calc R . . H8C H 0.0861 -0.0986 0.6334 0.043 Uiso 1 1 calc R . . C9 C 0.66916(18) 0.44041(15) 0.64647(11) 0.0252(3) Uani 1 1 d . . . H9A H 0.7031 0.4776 0.7184 0.030 Uiso 1 1 calc R . . H9B H 0.6109 0.4994 0.6258 0.030 Uiso 1 1 calc R . . C10 C 0.82072(19) 0.45708(18) 0.59263(13) 0.0343(4) Uani 1 1 d . . . H10A H 0.8827 0.4037 0.6157 0.051 Uiso 1 1 calc R . . H10B H 0.8887 0.5590 0.6063 0.051 Uiso 1 1 calc R . . H10C H 0.7881 0.4192 0.5214 0.051 Uiso 1 1 calc R . . C11 C 0.60549(16) 0.22899(15) 0.79762(10) 0.0203(3) Uani 1 1 d . . . C12 C 0.76778(17) 0.28657(15) 0.83406(10) 0.0224(3) Uani 1 1 d . . . H12 H 0.8529 0.3111 0.7935 0.027 Uiso 1 1 calc R . . C13 C 0.79668(17) 0.30603(15) 0.93792(10) 0.0220(3) Uani 1 1 d . . . H13 H 0.9025 0.3424 0.9732 0.026 Uiso 1 1 calc R . . C14 C 0.65531(16) 0.26667(14) 0.98205(10) 0.0199(3) Uani 1 1 d . . . C15 C 0.41372(16) 0.22592(15) 1.10964(10) 0.0205(3) Uani 1 1 d . . . C16 C 0.30754(18) 0.08945(15) 1.11128(10) 0.0243(3) Uani 1 1 d . . . H16 H 0.3494 0.0154 1.1138 0.029 Uiso 1 1 calc R . . C17 C 0.14038(18) 0.06116(16) 1.10922(11) 0.0281(3) Uani 1 1 d . . . H17 H 0.0687 -0.0323 1.1096 0.034 Uiso 1 1 calc R . . C18 C 0.07826(18) 0.16889(17) 1.10664(11) 0.0279(3) Uani 1 1 d . . . H18 H -0.0357 0.1492 1.1052 0.033 Uiso 1 1 calc R . . C19 C 0.18313(18) 0.30563(16) 1.10612(11) 0.0259(3) Uani 1 1 d . . . H19 H 0.1408 0.3797 1.1048 0.031 Uiso 1 1 calc R . . C20 C 0.35033(17) 0.33428(15) 1.10748(10) 0.0231(3) Uani 1 1 d . . . H20 H 0.4216 0.4279 1.1069 0.028 Uiso 1 1 calc R . . C21 C 0.72008(16) 0.44169(14) 1.18066(10) 0.0199(3) Uani 1 1 d . . . C22 C 0.73505(17) 0.46247(16) 1.28363(10) 0.0234(3) Uani 1 1 d . . . H22 H 0.7065 0.3816 1.3115 0.028 Uiso 1 1 calc R . . C23 C 0.79117(18) 0.60026(17) 1.34549(11) 0.0267(3) Uani 1 1 d . . . H23 H 0.7983 0.6129 1.4152 0.032 Uiso 1 1 calc R . . C24 C 0.83665(17) 0.71914(16) 1.30557(11) 0.0258(3) Uani 1 1 d . . . H24 H 0.8753 0.8133 1.3477 0.031 Uiso 1 1 calc R . . C25 C 0.82542(17) 0.69969(16) 1.20352(11) 0.0254(3) Uani 1 1 d . . . H25 H 0.8581 0.7811 1.1761 0.030 Uiso 1 1 calc R . . C26 C 0.76672(17) 0.56199(15) 1.14094(11) 0.0232(3) Uani 1 1 d . . . H26 H 0.7584 0.5499 1.0713 0.028 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 0.02149(17) 0.01989(17) 0.01742(16) 0.00490(13) 0.00106(12) 0.00726(13) S1 0.01774(16) 0.02778(18) 0.01739(15) 0.00542(13) 0.00137(11) 0.00759(13) N2 0.0188(5) 0.0212(6) 0.0181(5) 0.0036(4) 0.0003(4) 0.0065(4) N1 0.0186(5) 0.0221(6) 0.0191(5) 0.0059(4) 0.0028(4) 0.0076(4) B1 0.0185(7) 0.0242(7) 0.0183(7) 0.0042(6) 0.0031(5) 0.0093(6) C1 0.0178(6) 0.0240(7) 0.0185(6) 0.0051(5) 0.0035(5) 0.0092(5) C2 0.0178(6) 0.0234(7) 0.0174(6) 0.0027(5) 0.0022(5) 0.0088(5) C3 0.0212(6) 0.0245(7) 0.0198(6) 0.0060(5) 0.0025(5) 0.0085(5) C4 0.0260(7) 0.0319(8) 0.0176(6) 0.0058(5) 0.0011(5) 0.0130(6) C5 0.0222(7) 0.0289(7) 0.0197(6) 0.0014(5) -0.0012(5) 0.0093(6) C6 0.0198(6) 0.0237(7) 0.0220(6) 0.0025(5) 0.0013(5) 0.0072(5) C7 0.0232(7) 0.0219(7) 0.0232(6) 0.0074(5) 0.0038(5) 0.0086(5) C8 0.0254(7) 0.0258(7) 0.0353(8) 0.0113(6) 0.0097(6) 0.0074(6) C9 0.0277(7) 0.0204(7) 0.0239(7) 0.0039(5) -0.0016(5) 0.0051(6) C10 0.0262(8) 0.0319(8) 0.0375(9) 0.0113(7) 0.0011(6) -0.0004(6) C11 0.0214(6) 0.0220(6) 0.0185(6) 0.0055(5) 0.0042(5) 0.0087(5) C12 0.0211(6) 0.0260(7) 0.0202(6) 0.0060(5) 0.0036(5) 0.0080(5) C13 0.0196(6) 0.0248(7) 0.0204(6) 0.0049(5) 0.0000(5) 0.0070(5) C14 0.0210(6) 0.0205(6) 0.0174(6) 0.0031(5) -0.0007(5) 0.0076(5) C15 0.0218(6) 0.0220(7) 0.0158(6) 0.0042(5) 0.0014(5) 0.0054(5) C16 0.0284(7) 0.0216(7) 0.0207(6) 0.0046(5) 0.0025(5) 0.0064(6) C17 0.0265(7) 0.0261(7) 0.0247(7) 0.0071(6) 0.0031(6) -0.0002(6) C18 0.0214(7) 0.0360(8) 0.0209(7) 0.0042(6) 0.0023(5) 0.0049(6) C19 0.0250(7) 0.0295(7) 0.0226(7) 0.0036(6) 0.0011(5) 0.0107(6) C20 0.0235(7) 0.0213(7) 0.0220(6) 0.0041(5) 0.0022(5) 0.0057(5) C21 0.0176(6) 0.0215(6) 0.0195(6) 0.0033(5) 0.0013(5) 0.0066(5) C22 0.0244(7) 0.0255(7) 0.0206(6) 0.0052(5) 0.0015(5) 0.0095(6) C23 0.0253(7) 0.0323(8) 0.0208(6) 0.0004(6) 0.0013(5) 0.0119(6) C24 0.0184(6) 0.0236(7) 0.0323(8) -0.0009(6) 0.0022(5) 0.0082(5) C25 0.0187(6) 0.0221(7) 0.0346(8) 0.0073(6) 0.0046(5) 0.0059(5) C26 0.0209(6) 0.0250(7) 0.0235(7) 0.0070(5) 0.0029(5) 0.0073(5) _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 C14 1.8195(14) . ? P1 C21 1.8340(14) . ? P1 C15 1.8395(14) . ? S1 C14 1.7243(13) . ? S1 C11 1.7262(14) . ? N2 C2 1.3964(16) . ? N2 B1 1.430(2) . ? N2 C9 1.4554(18) . ? N1 C1 1.3933(17) . ? N1 B1 1.4357(19) . ? N1 C7 1.4605(18) . ? B1 C11 1.557(2) . ? C1 C6 1.3941(18) . ? C1 C2 1.4102(19) . ? C2 C3 1.3864(19) . ? C3 C4 1.3952(19) . ? C3 H3 0.9500 . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C5 C6 1.398(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.519(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.525(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3754(19) . ? C12 C13 1.4225(19) . ? C12 H12 0.9500 . ? C13 C14 1.378(2) . ? C13 H13 0.9500 . ? C15 C16 1.395(2) . ? C15 C20 1.399(2) . ? C16 C17 1.394(2) . ? C16 H16 0.9500 . ? C17 C18 1.387(2) . ? C17 H17 0.9500 . ? C18 C19 1.389(2) . ? C18 H18 0.9500 . ? C19 C20 1.394(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.398(2) . ? C21 C22 1.4016(19) . ? C22 C23 1.391(2) . ? C22 H22 0.9500 . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 C25 1.390(2) . ? C24 H24 0.9500 . ? C25 C26 1.395(2) . ? C25 H25 0.9500 . ? C26 H26 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 C14 P1 C21 103.55(6) . . ? C14 P1 C15 99.50(6) . . ? C21 P1 C15 100.19(6) . . ? C14 S1 C11 93.84(7) . . ? C2 N2 B1 108.22(11) . . ? C2 N2 C9 121.79(11) . . ? B1 N2 C9 129.91(12) . . ? C1 N1 B1 108.05(11) . . ? C1 N1 C7 122.09(11) . . ? B1 N1 C7 129.68(12) . . ? N2 B1 N1 106.61(12) . . ? N2 B1 C11 125.28(13) . . ? N1 B1 C11 128.08(13) . . ? N1 C1 C6 130.95(13) . . ? N1 C1 C2 108.68(11) . . ? C6 C1 C2 120.37(12) . . ? C3 C2 N2 130.31(13) . . ? C3 C2 C1 121.25(12) . . ? N2 C2 C1 108.43(11) . . ? C2 C3 C4 118.29(13) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 120.62(13) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 121.50(13) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C1 C6 C5 117.92(13) . . ? C1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? N1 C7 C8 113.35(12) . . ? N1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 113.09(12) . . ? N2 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 B1 129.64(13) . . ? C12 C11 S1 109.35(10) . . ? B1 C11 S1 120.95(10) . . ? C11 C12 C13 113.93(13) . . ? C11 C12 H12 123.0 . . ? C13 C12 H12 123.0 . . ? C14 C13 C12 113.05(12) . . ? C14 C13 H13 123.5 . . ? C12 C13 H13 123.5 . . ? C13 C14 S1 109.81(10) . . ? C13 C14 P1 128.49(10) . . ? S1 C14 P1 121.17(8) . . ? C16 C15 C20 119.09(13) . . ? C16 C15 P1 117.97(11) . . ? C20 C15 P1 122.95(11) . . ? C17 C16 C15 120.33(14) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 120.30(14) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 119.84(14) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 120.11(14) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 120.33(13) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C26 C21 C22 118.84(13) . . ? C26 C21 P1 125.48(11) . . ? C22 C21 P1 115.64(11) . . ? C23 C22 C21 120.75(14) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 120.08(14) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 119.61(13) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.70(14) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 120.00(13) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.302 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.061 #============================================================================== data_compound9 _database_code_depnum_ccdc_archive 'CCDC 873275' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 B N2 P S2' _chemical_formula_sum 'C26 H26 B N2 P S2' _chemical_formula_weight 472.39 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 18.8093(7) _cell_length_b 8.1110(3) _cell_length_c 17.4215(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.3641(19) _cell_angle_gamma 90.00 _cell_volume 2381.42(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 112393 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9269 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57086 _diffrn_reflns_av_R_equivalents 0.093 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5415 _reflns_number_gt 4190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+1.9190P] 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 5415 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 S1 S 0.17577(3) 0.23769(7) 0.49816(3) 0.02613(14) Uani 1 1 d . . . S2 S 0.34997(4) -0.00666(7) 0.65433(4) 0.03082(15) Uani 1 1 d . . . P1 P 0.32804(3) 0.22513(7) 0.66681(3) 0.02390(14) Uani 1 1 d . . . N1 N -0.06733(11) 0.2329(2) 0.39096(11) 0.0241(4) Uani 1 1 d . . . N2 N -0.00321(11) 0.3779(2) 0.32666(11) 0.0244(4) Uani 1 1 d . . . B1 B 0.00782(15) 0.2994(3) 0.40500(16) 0.0247(5) Uani 1 1 d . . . C1 C -0.12247(13) 0.2723(3) 0.30737(13) 0.0244(4) Uani 1 1 d . . . C2 C -0.08318(13) 0.3614(3) 0.26806(13) 0.0249(4) Uani 1 1 d . . . C3 C -0.12466(14) 0.4175(3) 0.18440(14) 0.0277(5) Uani 1 1 d . . . H3 H -0.0987 0.4782 0.1576 0.033 Uiso 1 1 calc R . . C4 C -0.20520(14) 0.3823(3) 0.14094(14) 0.0312(5) Uani 1 1 d . . . H4 H -0.2348 0.4210 0.0840 0.037 Uiso 1 1 calc R . . C5 C -0.24330(14) 0.2913(3) 0.17963(15) 0.0318(5) Uani 1 1 d . . . H5 H -0.2982 0.2668 0.1480 0.038 Uiso 1 1 calc R . . C6 C -0.20270(13) 0.2356(3) 0.26351(14) 0.0286(5) Uani 1 1 d . . . H6 H -0.2290 0.1744 0.2899 0.034 Uiso 1 1 calc R . . C7 C -0.09159(13) 0.1442(3) 0.44877(14) 0.0265(5) Uani 1 1 d . . . H7A H -0.0437 0.1042 0.4989 0.032 Uiso 1 1 calc R . . H7B H -0.1236 0.0470 0.4186 0.032 Uiso 1 1 calc R . . C8 C -0.13997(15) 0.2525(3) 0.47980(16) 0.0343(5) Uani 1 1 d . . . H8A H -0.1062 0.3408 0.5162 0.051 Uiso 1 1 calc R . . H8B H -0.1600 0.1854 0.5128 0.051 Uiso 1 1 calc R . . H8C H -0.1847 0.3008 0.4303 0.051 Uiso 1 1 calc R . . C9 C 0.05319(13) 0.4674(3) 0.30477(14) 0.0262(5) Uani 1 1 d . . . H9A H 0.0998 0.4995 0.3583 0.031 Uiso 1 1 calc R . . H9B H 0.0277 0.5696 0.2737 0.031 Uiso 1 1 calc R . . C10 C 0.08109(15) 0.3662(3) 0.24969(16) 0.0333(5) Uani 1 1 d . . . H10A H 0.1096 0.2684 0.2816 0.050 Uiso 1 1 calc R . . H10B H 0.1166 0.4332 0.2349 0.050 Uiso 1 1 calc R . . H10C H 0.0351 0.3319 0.1972 0.050 Uiso 1 1 calc R . . C11 C 0.08493(13) 0.2961(3) 0.49154(14) 0.0251(4) Uani 1 1 d . . . C12 C 0.09366(13) 0.3409(3) 0.57126(13) 0.0264(5) Uani 1 1 d . . . H12 H 0.0504 0.3754 0.5816 0.032 Uiso 1 1 calc R . . C13 C 0.17261(13) 0.3313(3) 0.63687(14) 0.0259(5) Uani 1 1 d . . . H13 H 0.1878 0.3608 0.6948 0.031 Uiso 1 1 calc R . . C14 C 0.22457(13) 0.2745(3) 0.60712(13) 0.0247(4) Uani 1 1 d . . . C15 C 0.35131(13) 0.2874(3) 0.77568(13) 0.0252(4) Uani 1 1 d . . . C16 C 0.32191(13) 0.1927(3) 0.82259(14) 0.0291(5) Uani 1 1 d . . . H16 H 0.2912 0.0970 0.7977 0.035 Uiso 1 1 calc R . . C17 C 0.33768(14) 0.2388(3) 0.90530(14) 0.0319(5) Uani 1 1 d . . . H17 H 0.3175 0.1749 0.9370 0.038 Uiso 1 1 calc R . . C18 C 0.38296(14) 0.3785(3) 0.94179(14) 0.0322(5) Uani 1 1 d . . . H18 H 0.3932 0.4107 0.9982 0.039 Uiso 1 1 calc R . . C19 C 0.41307(14) 0.4708(3) 0.89622(14) 0.0321(5) Uani 1 1 d . . . H19 H 0.4448 0.5650 0.9218 0.038 Uiso 1 1 calc R . . C20 C 0.39700(13) 0.4261(3) 0.81286(14) 0.0295(5) Uani 1 1 d . . . H20 H 0.4173 0.4904 0.7815 0.035 Uiso 1 1 calc R . . C21 C 0.38117(13) 0.3672(3) 0.63054(13) 0.0255(5) Uani 1 1 d . . . C22 C 0.45789(14) 0.3266(3) 0.64410(14) 0.0307(5) Uani 1 1 d . . . H22 H 0.4811 0.2253 0.6709 0.037 Uiso 1 1 calc R . . C23 C 0.50023(14) 0.4348(3) 0.61824(15) 0.0345(5) Uani 1 1 d . . . H23 H 0.5525 0.4072 0.6273 0.041 Uiso 1 1 calc R . . C24 C 0.46681(15) 0.5828(3) 0.57926(15) 0.0347(5) Uani 1 1 d . . . H24 H 0.4961 0.6558 0.5614 0.042 Uiso 1 1 calc R . . C25 C 0.39093(15) 0.6246(3) 0.56623(15) 0.0331(5) Uani 1 1 d . . . H25 H 0.3682 0.7263 0.5395 0.040 Uiso 1 1 calc R . . C26 C 0.34808(14) 0.5178(3) 0.59220(14) 0.0288(5) Uani 1 1 d . . . H26 H 0.2963 0.5470 0.5839 0.035 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 S1 0.0276(3) 0.0312(3) 0.0217(3) -0.0028(2) 0.0129(2) -0.0006(2) S2 0.0396(3) 0.0243(3) 0.0311(3) -0.0006(2) 0.0180(3) 0.0019(2) P1 0.0279(3) 0.0247(3) 0.0212(3) -0.0005(2) 0.0128(2) -0.0005(2) N1 0.0295(10) 0.0224(9) 0.0238(9) 0.0008(7) 0.0149(8) 0.0004(7) N2 0.0291(10) 0.0234(9) 0.0249(9) 0.0000(7) 0.0157(8) -0.0009(7) B1 0.0322(13) 0.0185(12) 0.0269(12) -0.0025(9) 0.0161(11) 0.0004(9) C1 0.0322(12) 0.0192(11) 0.0244(10) -0.0010(8) 0.0148(9) 0.0020(8) C2 0.0317(12) 0.0203(11) 0.0269(11) -0.0028(8) 0.0167(9) 0.0009(8) C3 0.0373(13) 0.0246(11) 0.0257(11) 0.0018(9) 0.0181(10) 0.0044(9) C4 0.0348(13) 0.0337(13) 0.0250(11) 0.0005(9) 0.0132(10) 0.0070(10) C5 0.0280(12) 0.0338(13) 0.0317(12) -0.0027(10) 0.0115(10) 0.0023(10) C6 0.0296(12) 0.0280(12) 0.0317(12) -0.0031(9) 0.0168(10) -0.0002(9) C7 0.0321(12) 0.0229(11) 0.0276(11) 0.0044(8) 0.0162(9) -0.0011(9) C8 0.0423(14) 0.0350(14) 0.0353(13) 0.0047(10) 0.0260(11) 0.0031(10) C9 0.0322(12) 0.0231(11) 0.0280(11) 0.0005(9) 0.0177(9) -0.0024(9) C10 0.0433(14) 0.0286(13) 0.0391(13) 0.0006(10) 0.0285(11) -0.0007(10) C11 0.0299(11) 0.0212(11) 0.0286(11) 0.0017(8) 0.0169(9) -0.0004(8) C12 0.0310(12) 0.0248(11) 0.0272(11) 0.0024(9) 0.0163(9) 0.0016(9) C13 0.0347(12) 0.0228(11) 0.0240(10) -0.0006(8) 0.0164(9) -0.0013(9) C14 0.0285(11) 0.0251(11) 0.0218(10) -0.0019(8) 0.0122(9) -0.0034(8) C15 0.0275(11) 0.0266(11) 0.0217(10) -0.0003(8) 0.0112(9) 0.0026(9) C16 0.0305(12) 0.0314(12) 0.0259(11) 0.0016(9) 0.0130(9) 0.0000(9) C17 0.0335(12) 0.0395(14) 0.0267(11) 0.0062(10) 0.0168(10) 0.0059(10) C18 0.0379(13) 0.0357(13) 0.0223(11) 0.0007(9) 0.0127(10) 0.0106(10) C19 0.0373(13) 0.0314(13) 0.0250(11) -0.0041(9) 0.0116(10) 0.0011(10) C20 0.0325(12) 0.0307(12) 0.0256(11) 0.0016(9) 0.0133(9) 0.0011(9) C21 0.0298(11) 0.0271(12) 0.0215(10) -0.0029(8) 0.0131(9) -0.0034(9) C22 0.0328(12) 0.0327(13) 0.0277(11) -0.0010(9) 0.0144(10) 0.0008(10) C23 0.0293(12) 0.0435(15) 0.0339(12) -0.0074(11) 0.0171(10) -0.0062(10) C24 0.0414(14) 0.0365(14) 0.0328(12) -0.0069(10) 0.0224(11) -0.0129(11) C25 0.0459(14) 0.0252(12) 0.0323(12) -0.0008(9) 0.0211(11) -0.0025(10) C26 0.0335(12) 0.0286(12) 0.0290(11) -0.0016(9) 0.0181(10) -0.0011(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 S1 C11 1.727(2) . ? S1 C14 1.728(2) . ? S2 P1 1.9574(8) . ? P1 C14 1.798(2) . ? P1 C21 1.813(2) . ? P1 C15 1.818(2) . ? N1 C1 1.399(3) . ? N1 B1 1.429(3) . ? N1 C7 1.465(3) . ? N2 C2 1.400(3) . ? N2 B1 1.435(3) . ? N2 C9 1.468(3) . ? B1 C11 1.561(3) . ? C1 C6 1.388(3) . ? C1 C2 1.409(3) . ? C2 C3 1.389(3) . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.526(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.522(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.373(3) . ? C12 C13 1.418(3) . ? C12 H12 0.9500 . ? C13 C14 1.373(3) . ? C13 H13 0.9500 . ? C15 C20 1.389(3) . ? C15 C16 1.401(3) . ? C16 C17 1.387(3) . ? C16 H16 0.9500 . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C19 1.382(3) . ? C18 H18 0.9500 . ? C19 C20 1.394(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.394(3) . ? C21 C26 1.398(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.385(4) . ? C23 H23 0.9500 . ? C24 C25 1.384(3) . ? C24 H24 0.9500 . ? C25 C26 1.389(3) . ? C25 H25 0.9500 . ? C26 H26 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 C11 S1 C14 93.05(10) . . ? C14 P1 C21 106.23(10) . . ? C14 P1 C15 103.82(10) . . ? C21 P1 C15 105.82(10) . . ? C14 P1 S2 112.15(8) . . ? C21 P1 S2 113.32(8) . . ? C15 P1 S2 114.67(8) . . ? C1 N1 B1 108.14(17) . . ? C1 N1 C7 120.96(18) . . ? B1 N1 C7 130.84(19) . . ? C2 N2 B1 107.81(17) . . ? C2 N2 C9 121.61(17) . . ? B1 N2 C9 130.55(19) . . ? N1 B1 N2 106.89(19) . . ? N1 B1 C11 125.7(2) . . ? N2 B1 C11 127.3(2) . . ? C6 C1 N1 130.3(2) . . ? C6 C1 C2 121.3(2) . . ? N1 C1 C2 108.47(19) . . ? C3 C2 N2 130.9(2) . . ? C3 C2 C1 120.4(2) . . ? N2 C2 C1 108.68(18) . . ? C2 C3 C4 118.2(2) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C1 C6 C5 117.7(2) . . ? C1 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? N1 C7 C8 112.19(18) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 112.86(18) . . ? N2 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 B1 128.0(2) . . ? C12 C11 S1 109.55(17) . . ? B1 C11 S1 122.47(16) . . ? C11 C12 C13 114.39(19) . . ? C11 C12 H12 122.8 . . ? C13 C12 H12 122.8 . . ? C14 C13 C12 112.35(19) . . ? C14 C13 H13 123.8 . . ? C12 C13 H13 123.8 . . ? C13 C14 S1 110.64(16) . . ? C13 C14 P1 128.72(16) . . ? S1 C14 P1 120.49(12) . . ? C20 C15 C16 119.6(2) . . ? C20 C15 P1 121.58(17) . . ? C16 C15 P1 118.80(17) . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.2(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.2(2) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 120.0(2) . . ? C15 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C26 119.7(2) . . ? C22 C21 P1 118.70(17) . . ? C26 C21 P1 121.61(17) . . ? C23 C22 C21 119.7(2) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.9(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.1(2) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.638 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.064 #============================================================================== data_compound11 _database_code_depnum_ccdc_archive 'CCDC 873276' #TrackingRef '- compound2_3_4_5_6_7_8_9_11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H29 B N2 P S, C H3 O4 S' _chemical_formula_sum 'C28 H32 B N2 O4 P S2' _chemical_formula_weight 566.46 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' S S 0.1246 0.1234 '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 18.9789(4) _cell_length_b 8.33800(10) _cell_length_c 18.3001(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.0221(9) _cell_angle_gamma 90.00 _cell_volume 2737.78(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 52878 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9178 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54160 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7975 _reflns_number_gt 6236 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Disorder of O(2), O(3), O(4) on two positions (92:8) 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^)+(0.0426P)^2^+0.8944P] 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 7975 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 S1 S 0.205352(18) 0.35319(4) 0.08051(2) 0.01674(8) Uani 1 1 d . . . P1 P 0.317770(18) 0.57537(4) 0.04076(2) 0.01476(8) Uani 1 1 d . . . N1 N 0.04348(6) 0.25339(13) 0.12260(6) 0.0157(2) Uani 1 1 d . . . N2 N -0.01711(6) 0.20152(13) -0.00624(6) 0.0144(2) Uani 1 1 d . . . B1 B 0.05010(8) 0.26615(18) 0.04702(9) 0.0153(3) Uani 1 1 d . . . C1 C -0.02645(7) 0.18698(16) 0.11458(8) 0.0158(3) Uani 1 1 d . . . C2 C -0.06320(7) 0.15456(15) 0.03582(8) 0.0159(3) Uani 1 1 d . . . C3 C -0.13310(7) 0.08229(16) 0.01154(8) 0.0180(3) Uani 1 1 d . . . H3 H -0.1576 0.0583 -0.0414 0.022 Uiso 1 1 calc R . . C4 C -0.16610(8) 0.04602(17) 0.06762(8) 0.0204(3) Uani 1 1 d . . . H4 H -0.2135 -0.0046 0.0525 0.025 Uiso 1 1 calc R . . C5 C -0.13090(8) 0.08260(17) 0.14503(8) 0.0208(3) Uani 1 1 d . . . H5 H -0.1552 0.0594 0.1817 0.025 Uiso 1 1 calc R . . C6 C -0.06009(8) 0.15317(17) 0.16980(8) 0.0191(3) Uani 1 1 d . . . H6 H -0.0358 0.1772 0.2228 0.023 Uiso 1 1 calc R . . C7 C 0.09633(8) 0.28634(17) 0.19997(8) 0.0191(3) Uani 1 1 d . . . H7A H 0.0700 0.3432 0.2309 0.023 Uiso 1 1 calc R . . H7B H 0.1362 0.3579 0.1951 0.023 Uiso 1 1 calc R . . C8 C 0.13164(9) 0.13436(19) 0.24254(9) 0.0265(3) Uani 1 1 d . . . H8A H 0.0925 0.0631 0.2478 0.040 Uiso 1 1 calc R . . H8B H 0.1656 0.1625 0.2939 0.040 Uiso 1 1 calc R . . H8C H 0.1595 0.0796 0.2132 0.040 Uiso 1 1 calc R . . C9 C -0.03960(7) 0.17565(16) -0.08956(8) 0.0162(3) Uani 1 1 d . . . H9A H -0.0617 0.0673 -0.1016 0.019 Uiso 1 1 calc R . . H9B H 0.0051 0.1796 -0.1061 0.019 Uiso 1 1 calc R . . C10 C -0.09580(8) 0.29966(17) -0.13520(8) 0.0196(3) Uani 1 1 d . . . H10A H -0.1383 0.3029 -0.1160 0.029 Uiso 1 1 calc R . . H10B H -0.1131 0.2703 -0.1900 0.029 Uiso 1 1 calc R . . H10C H -0.0721 0.4054 -0.1289 0.029 Uiso 1 1 calc R . . C11 C 0.11320(7) 0.34858(15) 0.02306(8) 0.0154(3) Uani 1 1 d . . . C12 C 0.10350(7) 0.43986(17) -0.04245(8) 0.0185(3) Uani 1 1 d . . . H12 H 0.0567 0.4514 -0.0820 0.022 Uiso 1 1 calc R . . C13 C 0.16918(7) 0.51447(17) -0.04551(8) 0.0185(3) Uani 1 1 d . . . H13 H 0.1712 0.5820 -0.0866 0.022 Uiso 1 1 calc R . . C14 C 0.23005(7) 0.47819(15) 0.01791(8) 0.0156(2) Uani 1 1 d . . . C15 C 0.31987(7) 0.73972(16) 0.10500(8) 0.0166(3) Uani 1 1 d . . . C16 C 0.29980(7) 0.71030(17) 0.17096(8) 0.0193(3) Uani 1 1 d . . . H16 H 0.2885 0.6043 0.1827 0.023 Uiso 1 1 calc R . . C17 C 0.29647(8) 0.83661(18) 0.21919(9) 0.0227(3) Uani 1 1 d . . . H17 H 0.2826 0.8170 0.2638 0.027 Uiso 1 1 calc R . . C18 C 0.31340(8) 0.99140(18) 0.20245(9) 0.0242(3) Uani 1 1 d . . . H18 H 0.3101 1.0779 0.2350 0.029 Uiso 1 1 calc R . . C19 C 0.33506(8) 1.01962(17) 0.13822(9) 0.0235(3) Uani 1 1 d . . . H19 H 0.3478 1.1254 0.1279 0.028 Uiso 1 1 calc R . . C20 C 0.33840(7) 0.89575(16) 0.08867(8) 0.0194(3) Uani 1 1 d . . . H20 H 0.3530 0.9162 0.0445 0.023 Uiso 1 1 calc R . . C21 C 0.39376(7) 0.43994(16) 0.08483(8) 0.0169(3) Uani 1 1 d . . . C22 C 0.44090(8) 0.46096(18) 0.16053(8) 0.0208(3) Uani 1 1 d . . . H22 H 0.4307 0.5416 0.1924 0.025 Uiso 1 1 calc R . . C23 C 0.50310(8) 0.36237(19) 0.18889(9) 0.0252(3) Uani 1 1 d . . . H23 H 0.5359 0.3770 0.2402 0.030 Uiso 1 1 calc R . . C24 C 0.51753(8) 0.24349(19) 0.14311(9) 0.0257(3) Uani 1 1 d . . . H24 H 0.5606 0.1782 0.1626 0.031 Uiso 1 1 calc R . . C25 C 0.46915(9) 0.21935(19) 0.06868(9) 0.0265(3) Uani 1 1 d . . . H25 H 0.4783 0.1356 0.0378 0.032 Uiso 1 1 calc R . . C26 C 0.40726(8) 0.31760(18) 0.03935(9) 0.0231(3) Uani 1 1 d . . . H26 H 0.3742 0.3014 -0.0117 0.028 Uiso 1 1 calc R . . C27 C 0.32688(8) 0.64590(18) -0.04821(8) 0.0210(3) Uani 1 1 d . . . H27A H 0.3207 0.5559 -0.0842 0.031 Uiso 1 1 calc R . . H27B H 0.3763 0.6936 -0.0382 0.031 Uiso 1 1 calc R . . H27C H 0.2886 0.7268 -0.0709 0.031 Uiso 1 1 calc R . . S2 S 0.32313(2) 0.39366(4) 0.34701(2) 0.02205(9) Uani 1 1 d . . . O1 O 0.30064(6) 0.23682(14) 0.36430(6) 0.0298(3) Uani 1 1 d . A . O2 O 0.38354(7) 0.36585(15) 0.30475(7) 0.0295(3) Uani 0.9235(18) 1 d P A 1 O3 O 0.26628(7) 0.48208(18) 0.28955(8) 0.0393(4) Uani 0.9235(18) 1 d P A 1 O4 O 0.36101(8) 0.48471(14) 0.41653(7) 0.0332(3) Uani 0.9235(18) 1 d P A 1 O2B O 0.4159(7) 0.3857(14) 0.3838(7) 0.015(3) Uiso 0.0765(18) 1 d P A 2 O3B O 0.3205(8) 0.3680(17) 0.2569(8) 0.025(3) Uiso 0.0765(18) 1 d P A 2 O4B O 0.3046(8) 0.5374(18) 0.3577(9) 0.030(4) Uiso 0.0765(18) 1 d P A 2 C28 C 0.44830(11) 0.2747(3) 0.35085(14) 0.0495(5) Uani 1 1 d . . . H28A H 0.4831 0.2619 0.3218 0.074 Uiso 0.9235(18) 1 calc PR A 1 H28B H 0.4323 0.1689 0.3626 0.074 Uiso 0.9235(18) 1 calc PR A 1 H28C H 0.4731 0.3321 0.3991 0.074 Uiso 0.9235(18) 1 calc PR A 1 H28D H 0.5025 0.2778 0.3758 0.074 Uiso 0.0765(18) 1 calc PR A 2 H28E H 0.4362 0.2984 0.2957 0.074 Uiso 0.0765(18) 1 calc PR A 2 H28F H 0.4296 0.1678 0.3572 0.074 Uiso 0.0765(18) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01364(15) 0.01687(16) 0.01829(16) 0.00348(12) 0.00327(12) -0.00134(12) P1 0.01315(15) 0.01455(16) 0.01660(17) 0.00032(12) 0.00488(13) -0.00136(12) N1 0.0143(5) 0.0157(5) 0.0164(5) -0.0010(4) 0.0039(4) -0.0012(4) N2 0.0140(5) 0.0139(5) 0.0155(5) -0.0003(4) 0.0048(4) -0.0007(4) B1 0.0148(6) 0.0128(6) 0.0182(7) 0.0005(5) 0.0050(6) 0.0006(5) C1 0.0143(6) 0.0143(6) 0.0184(6) 0.0016(5) 0.0049(5) 0.0007(5) C2 0.0161(6) 0.0133(6) 0.0188(6) 0.0019(5) 0.0065(5) 0.0017(5) C3 0.0157(6) 0.0159(6) 0.0202(7) 0.0007(5) 0.0029(5) -0.0004(5) C4 0.0145(6) 0.0200(7) 0.0261(7) 0.0049(6) 0.0057(5) -0.0007(5) C5 0.0186(6) 0.0224(7) 0.0234(7) 0.0061(6) 0.0098(6) 0.0013(5) C6 0.0191(6) 0.0207(7) 0.0175(7) 0.0023(5) 0.0059(5) 0.0017(5) C7 0.0182(6) 0.0208(7) 0.0163(6) -0.0024(5) 0.0029(5) -0.0031(5) C8 0.0229(7) 0.0267(8) 0.0240(8) 0.0038(6) -0.0004(6) -0.0022(6) C9 0.0163(6) 0.0160(6) 0.0163(6) -0.0020(5) 0.0052(5) -0.0006(5) C10 0.0183(6) 0.0202(6) 0.0186(7) 0.0022(5) 0.0035(5) 0.0011(5) C11 0.0141(6) 0.0140(6) 0.0170(6) -0.0008(5) 0.0037(5) 0.0002(5) C12 0.0152(6) 0.0193(6) 0.0189(7) 0.0009(5) 0.0027(5) -0.0008(5) C13 0.0177(6) 0.0196(6) 0.0174(6) 0.0023(5) 0.0044(5) -0.0014(5) C14 0.0144(6) 0.0143(6) 0.0181(6) 0.0005(5) 0.0052(5) -0.0012(5) C15 0.0128(6) 0.0163(6) 0.0191(7) -0.0006(5) 0.0031(5) 0.0005(5) C16 0.0167(6) 0.0199(7) 0.0208(7) -0.0010(5) 0.0056(5) -0.0024(5) C17 0.0180(7) 0.0275(8) 0.0220(7) -0.0048(6) 0.0057(6) -0.0007(6) C18 0.0181(7) 0.0230(7) 0.0284(8) -0.0082(6) 0.0034(6) 0.0020(6) C19 0.0187(7) 0.0162(6) 0.0318(8) -0.0007(6) 0.0028(6) 0.0008(5) C20 0.0151(6) 0.0179(6) 0.0232(7) 0.0013(5) 0.0035(5) 0.0002(5) C21 0.0138(6) 0.0159(6) 0.0211(7) 0.0018(5) 0.0059(5) -0.0010(5) C22 0.0188(6) 0.0212(7) 0.0215(7) -0.0018(6) 0.0054(6) -0.0012(5) C23 0.0190(7) 0.0272(8) 0.0252(8) 0.0002(6) 0.0014(6) 0.0002(6) C24 0.0181(7) 0.0247(7) 0.0328(8) 0.0039(6) 0.0061(6) 0.0043(6) C25 0.0270(8) 0.0232(7) 0.0293(8) -0.0026(6) 0.0089(6) 0.0064(6) C26 0.0225(7) 0.0231(7) 0.0217(7) -0.0018(6) 0.0043(6) 0.0032(6) C27 0.0228(7) 0.0217(7) 0.0202(7) 0.0027(5) 0.0095(6) -0.0019(5) S2 0.02017(17) 0.02396(18) 0.02285(18) 0.00400(14) 0.00815(14) 0.00119(13) O1 0.0273(6) 0.0320(6) 0.0273(6) 0.0054(5) 0.0049(5) -0.0106(5) O2 0.0310(7) 0.0303(6) 0.0349(7) 0.0013(5) 0.0210(6) 0.0049(5) O3 0.0286(7) 0.0560(9) 0.0366(8) 0.0244(7) 0.0150(6) 0.0150(6) O4 0.0506(8) 0.0224(6) 0.0281(7) -0.0053(5) 0.0148(6) 0.0004(6) C28 0.0369(10) 0.0500(12) 0.0733(15) 0.0080(11) 0.0339(10) 0.0163(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 S1 C11 1.7225(13) . ? S1 C14 1.7229(14) . ? P1 C14 1.7746(13) . ? P1 C27 1.7918(14) . ? P1 C15 1.7974(14) . ? P1 C21 1.8021(14) . ? N1 C1 1.4009(17) . ? N1 B1 1.4329(19) . ? N1 C7 1.4699(17) . ? N2 C2 1.3963(17) . ? N2 B1 1.4342(18) . ? N2 C9 1.4592(17) . ? B1 C11 1.562(2) . ? C1 C6 1.3889(19) . ? C1 C2 1.4077(19) . ? C2 C3 1.3916(18) . ? C3 C4 1.399(2) . ? C3 H3 0.9500 . ? C4 C5 1.389(2) . ? C4 H4 0.9500 . ? C5 C6 1.400(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.524(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5243(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3808(19) . ? C12 C13 1.4104(19) . ? C12 H12 0.9500 . ? C13 C14 1.3781(18) . ? C13 H13 0.9500 . ? C15 C16 1.401(2) . ? C15 C20 1.4051(19) . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 C18 1.388(2) . ? C17 H17 0.9500 . ? C18 C19 1.386(2) . ? C18 H18 0.9500 . ? C19 C20 1.389(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.392(2) . ? C21 C22 1.3936(19) . ? C22 C23 1.393(2) . ? C22 H22 0.9500 . ? C23 C24 1.382(2) . ? C23 H23 0.9500 . ? C24 C25 1.387(2) . ? C24 H24 0.9500 . ? C25 C26 1.388(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? S2 O4B 1.282(15) . ? S2 O3 1.4401(13) . ? S2 O1 1.4424(11) . ? S2 O4 1.4544(13) . ? S2 O2 1.5950(12) . ? S2 O3B 1.647(14) . ? S2 O2B 1.668(12) . ? O2 C28 1.457(2) . ? O2B C28 1.357(12) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C28 H28D 0.9800 . ? C28 H28E 0.9800 . ? C28 H28F 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 S1 C14 92.86(6) . . ? C14 P1 C27 107.26(7) . . ? C14 P1 C15 108.75(6) . . ? C27 P1 C15 110.85(7) . . ? C14 P1 C21 111.83(6) . . ? C27 P1 C21 108.19(7) . . ? C15 P1 C21 109.95(6) . . ? C1 N1 B1 107.83(11) . . ? C1 N1 C7 120.04(11) . . ? B1 N1 C7 131.99(11) . . ? C2 N2 B1 107.99(11) . . ? C2 N2 C9 120.80(11) . . ? B1 N2 C9 131.16(11) . . ? N1 B1 N2 106.85(11) . . ? N1 B1 C11 128.30(12) . . ? N2 B1 C11 124.60(12) . . ? C6 C1 N1 130.43(12) . . ? C6 C1 C2 120.94(12) . . ? N1 C1 C2 108.64(11) . . ? C3 C2 N2 130.45(13) . . ? C3 C2 C1 120.85(12) . . ? N2 C2 C1 108.67(11) . . ? C2 C3 C4 117.88(13) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 121.30(13) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.94(13) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 118.04(13) . . ? C1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? N1 C7 C8 112.66(11) . . ? N1 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? N1 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 112.73(11) . . ? N2 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 B1 126.06(12) . . ? C12 C11 S1 109.82(10) . . ? B1 C11 S1 123.86(10) . . ? C11 C12 C13 114.09(12) . . ? C11 C12 H12 123.0 . . ? C13 C12 H12 123.0 . . ? C14 C13 C12 112.26(12) . . ? C14 C13 H13 123.9 . . ? C12 C13 H13 123.9 . . ? C13 C14 S1 110.96(10) . . ? C13 C14 P1 124.25(10) . . ? S1 C14 P1 123.86(8) . . ? C16 C15 C20 120.17(13) . . ? C16 C15 P1 118.41(10) . . ? C20 C15 P1 121.37(11) . . ? C17 C16 C15 119.76(13) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 120.21(14) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 119.93(14) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 121.10(14) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 118.80(14) . . ? C19 C20 H20 120.6 . . ? C15 C20 H20 120.6 . . ? C26 C21 C22 120.19(13) . . ? C26 C21 P1 117.90(10) . . ? C22 C21 P1 121.80(11) . . ? C23 C22 C21 119.20(13) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C24 C23 C22 120.59(14) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.07(14) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 119.99(14) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 119.90(14) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? P1 C27 H27A 109.5 . . ? P1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? P1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O4B S2 O3 57.0(7) . . ? O4B S2 O1 134.3(7) . . ? O3 S2 O1 114.80(8) . . ? O4B S2 O4 57.4(7) . . ? O3 S2 O4 114.24(9) . . ? O1 S2 O4 112.24(7) . . ? O4B S2 O2 119.1(7) . . ? O3 S2 O2 101.90(7) . . ? O1 S2 O2 106.59(7) . . ? O4 S2 O2 105.76(7) . . ? O4B S2 O3B 110.7(8) . . ? O3 S2 O3B 64.2(5) . . ? O1 S2 O3B 100.8(5) . . ? O4 S2 O3B 142.1(5) . . ? O2 S2 O3B 44.6(5) . . ? O4B S2 O2B 106.3(8) . . ? O3 S2 O2B 139.1(4) . . ? O1 S2 O2B 103.0(4) . . ? O4 S2 O2B 60.8(4) . . ? O2 S2 O2B 50.2(4) . . ? O3B S2 O2B 94.8(6) . . ? C28 O2 S2 113.52(11) . . ? C28 O2B S2 114.8(8) . . ? O2B C28 O2 58.9(5) . . ? O2B C28 H28A 143.1 . . ? O2 C28 H28A 109.5 . . ? O2B C28 H28B 107.4 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2B C28 H28C 54.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O2B C28 H28D 109.5 . . ? O2 C28 H28D 144.6 . . ? H28A C28 H28D 57.7 . . ? H28B C28 H28D 105.9 . . ? H28C C28 H28D 56.3 . . ? O2B C28 H28E 109.5 . . ? O2 C28 H28E 55.2 . . ? H28A C28 H28E 55.6 . . ? H28B C28 H28E 115.0 . . ? H28C C28 H28E 135.5 . . ? H28D C28 H28E 109.5 . . ? O2B C28 H28F 109.5 . . ? O2 C28 H28F 105.9 . . ? H28A C28 H28F 107.4 . . ? H28B C28 H28F 5.6 . . ? H28C C28 H28F 115.0 . . ? H28D C28 H28F 109.5 . . ? H28E C28 H28F 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 C1 N1 B1 N2 -1.49(14) . . . . ? C7 N1 B1 N2 174.01(12) . . . . ? C1 N1 B1 C11 172.89(13) . . . . ? C7 N1 B1 C11 -11.6(2) . . . . ? C2 N2 B1 N1 1.17(14) . . . . ? C9 N2 B1 N1 -176.28(12) . . . . ? C2 N2 B1 C11 -173.47(12) . . . . ? C9 N2 B1 C11 9.1(2) . . . . ? B1 N1 C1 C6 -178.69(14) . . . . ? C7 N1 C1 C6 5.2(2) . . . . ? B1 N1 C1 C2 1.26(14) . . . . ? C7 N1 C1 C2 -174.88(11) . . . . ? B1 N2 C2 C3 -178.35(14) . . . . ? C9 N2 C2 C3 -0.6(2) . . . . ? B1 N2 C2 C1 -0.41(14) . . . . ? C9 N2 C2 C1 177.35(11) . . . . ? C6 C1 C2 C3 -2.4(2) . . . . ? N1 C1 C2 C3 177.64(12) . . . . ? C6 C1 C2 N2 179.43(12) . . . . ? N1 C1 C2 N2 -0.53(15) . . . . ? N2 C2 C3 C4 178.97(13) . . . . ? C1 C2 C3 C4 1.24(19) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C3 C4 C5 C6 -1.8(2) . . . . ? N1 C1 C6 C5 -178.64(13) . . . . ? C2 C1 C6 C5 1.4(2) . . . . ? C4 C5 C6 C1 0.7(2) . . . . ? C1 N1 C7 C8 73.69(16) . . . . ? B1 N1 C7 C8 -101.36(17) . . . . ? C2 N2 C9 C10 78.51(15) . . . . ? B1 N2 C9 C10 -104.31(16) . . . . ? N1 B1 C11 C12 -139.91(15) . . . . ? N2 B1 C11 C12 33.6(2) . . . . ? N1 B1 C11 S1 33.7(2) . . . . ? N2 B1 C11 S1 -152.80(11) . . . . ? C14 S1 C11 C12 0.76(11) . . . . ? C14 S1 C11 B1 -173.78(12) . . . . ? B1 C11 C12 C13 173.37(13) . . . . ? S1 C11 C12 C13 -1.02(16) . . . . ? C11 C12 C13 C14 0.80(18) . . . . ? C12 C13 C14 S1 -0.20(15) . . . . ? C12 C13 C14 P1 -169.49(10) . . . . ? C11 S1 C14 C13 -0.32(11) . . . . ? C11 S1 C14 P1 169.02(9) . . . . ? C27 P1 C14 C13 -27.28(14) . . . . ? C15 P1 C14 C13 92.66(13) . . . . ? C21 P1 C14 C13 -145.74(12) . . . . ? C27 P1 C14 S1 164.79(9) . . . . ? C15 P1 C14 S1 -75.28(10) . . . . ? C21 P1 C14 S1 46.33(11) . . . . ? C14 P1 C15 C16 50.70(12) . . . . ? C27 P1 C15 C16 168.38(10) . . . . ? C21 P1 C15 C16 -72.04(12) . . . . ? C14 P1 C15 C20 -126.95(11) . . . . ? C27 P1 C15 C20 -9.27(13) . . . . ? C21 P1 C15 C20 110.31(11) . . . . ? C20 C15 C16 C17 1.6(2) . . . . ? P1 C15 C16 C17 -176.09(10) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? C16 C17 C18 C19 -1.2(2) . . . . ? C17 C18 C19 C20 1.7(2) . . . . ? C18 C19 C20 C15 -0.5(2) . . . . ? C16 C15 C20 C19 -1.2(2) . . . . ? P1 C15 C20 C19 176.44(10) . . . . ? C14 P1 C21 C26 67.93(13) . . . . ? C27 P1 C21 C26 -49.97(13) . . . . ? C15 P1 C21 C26 -171.16(11) . . . . ? C14 P1 C21 C22 -115.91(12) . . . . ? C27 P1 C21 C22 126.18(12) . . . . ? C15 P1 C21 C22 5.00(14) . . . . ? C26 C21 C22 C23 2.5(2) . . . . ? P1 C21 C22 C23 -173.54(11) . . . . ? C21 C22 C23 C24 -0.9(2) . . . . ? C22 C23 C24 C25 -1.2(2) . . . . ? C23 C24 C25 C26 1.8(2) . . . . ? C24 C25 C26 C21 -0.2(2) . . . . ? C22 C21 C26 C25 -2.0(2) . . . . ? P1 C21 C26 C25 174.24(12) . . . . ? O4B S2 O2 C28 122.2(8) . . . . ? O3 S2 O2 C28 -179.14(14) . . . . ? O1 S2 O2 C28 -58.47(14) . . . . ? O4 S2 O2 C28 61.16(14) . . . . ? O3B S2 O2 C28 -147.1(7) . . . . ? O2B S2 O2 C28 34.8(5) . . . . ? O4B S2 O2B C28 -152.7(10) . . . . ? O3 S2 O2B C28 -94.6(9) . . . . ? O1 S2 O2B C28 62.7(8) . . . . ? O4 S2 O2B C28 171.2(10) . . . . ? O2 S2 O2B C28 -38.2(5) . . . . ? O3B S2 O2B C28 -39.5(9) . . . . ? S2 O2B C28 O2 37.4(5) . . . . ? S2 O2 C28 O2B -39.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.398 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.057 #===END