#------------------------------------------------------------------------------ #$Date: 2016-03-21 19:06:25 +0200 (Mon, 21 Mar 2016) $ #$Revision: 178835 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/10/89/4108973.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4108973 loop_ _publ_author_name 'David A. Delafuente' 'George W. Kosturko' 'Peter M. Graham' 'W. Hill Harman' 'William H. Myers' 'Yogesh Surendranath' 'Rachel C. Klet' 'Kevin D. Welch' 'Carl O. Trindle' 'Michal Sabat' 'W. Dean Harman' _publ_section_title ; Isomerization Dynamics and Control of the \h2/N Equilibrium for Pyridine Complexes ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 406 _journal_page_last 416 _journal_paper_doi 10.1021/ja066623f _journal_volume 129 _journal_year 2007 _chemical_formula_sum 'C22 H31 B F3 N8 O6 P S W' _chemical_formula_weight 818.24 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.734(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.0843(7) _cell_length_b 14.9833(8) _cell_length_c 16.5629(9) _cell_measurement_reflns_used 9288 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 32.494 _cell_measurement_theta_min 2.288 _cell_volume 2946.4(3) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 40372 _diffrn_reflns_theta_full 32.53 _diffrn_reflns_theta_max 32.53 _diffrn_reflns_theta_min 1.85 _exptl_absorpt_coefficient_mu 4.117 _exptl_absorpt_correction_T_max 0.801932 _exptl_absorpt_correction_T_min 0.680527 _exptl_absorpt_correction_type empirical _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.845 _exptl_crystal_description block _exptl_crystal_F_000 1616 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 2.258 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.141 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_matrix_type full _refine_ls_number_parameters 512 _refine_ls_number_reflns 10574 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.937 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0307 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.0638 _reflns_number_gt 8403 _reflns_number_total 10574 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ja066623fsi20061101_023601.cif _cod_data_source_block C22H31BN8O6F3PSW _cod_database_code 4108973 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 W W 0.383403(8) 0.438960(7) 0.222290(6) 0.01563(3) Uani 1 1 d S S 0.49511(6) 0.76433(5) 0.08498(4) 0.02307(14) Uani 1 1 d P P 0.24724(6) 0.53903(5) 0.27720(4) 0.01977(14) Uani 1 1 d F1 F 0.5497(2) 0.87707(15) -0.02156(13) 0.0554(6) Uani 1 1 d F2 F 0.41965(19) 0.92354(13) 0.04052(14) 0.0450(5) Uani 1 1 d F3 F 0.59054(19) 0.92203(13) 0.10319(15) 0.0489(6) Uani 1 1 d O1 O 0.09483(19) 0.55277(14) -0.08308(14) 0.0321(5) Uani 1 1 d O2 O 0.2033(2) 0.46280(15) -0.14541(13) 0.0329(5) Uani 1 1 d O3 O 0.20447(19) 0.32449(15) 0.12470(14) 0.0361(5) Uani 1 1 d O4 O 0.60450(18) 0.72421(15) 0.08934(15) 0.0366(5) Uani 1 1 d O5 O 0.46228(19) 0.77777(14) 0.16310(13) 0.0317(5) Uani 1 1 d O6 O 0.40993(18) 0.72971(14) 0.02070(14) 0.0305(5) Uani 1 1 d N1 N 0.3466(2) 0.42475(15) -0.00138(15) 0.0211(5) Uani 1 1 d N2 N 0.51252(18) 0.33589(15) 0.22520(13) 0.0196(4) Uani 1 1 d N3 N 0.59760(18) 0.32516(16) 0.29137(14) 0.0222(5) Uani 1 1 d N4 N 0.52199(19) 0.51959(15) 0.29523(14) 0.0211(5) Uani 1 1 d N5 N 0.60168(19) 0.47917(16) 0.35297(14) 0.0220(5) Uani 1 1 d N6 N 0.38345(18) 0.37200(14) 0.33954(13) 0.0189(4) Uani 1 1 d N7 N 0.48107(19) 0.35865(16) 0.39470(14) 0.0210(4) Uani 1 1 d N8 N 0.27571(19) 0.37140(15) 0.16550(14) 0.0202(4) Uani 1 1 d C2 C 0.2573(2) 0.48438(18) -0.00011(16) 0.0207(5) Uani 1 1 d C3 C 0.2658(2) 0.54368(17) 0.06067(16) 0.0198(5) Uani 1 1 d C4 C 0.3620(2) 0.54715(17) 0.12852(16) 0.0194(5) Uani 1 1 d C5 C 0.4573(2) 0.49021(19) 0.11691(17) 0.0214(5) Uani 1 1 d C6 C 0.4425(2) 0.43090(19) 0.05103(17) 0.0218(5) Uani 1 1 d C7 C 0.1596(2) 0.47448(19) -0.07222(17) 0.0239(6) Uani 1 1 d C8 C 0.1481(4) 0.6105(2) -0.1331(2) 0.0444(9) Uani 1 1 d C9 C 0.2095(4) 0.5488(3) -0.1801(3) 0.0503(11) Uani 1 1 d C10 C 0.0854(3) 0.3955(2) -0.0619(2) 0.0325(7) Uani 1 1 d C11 C 0.6564(3) 0.2512(2) 0.2803(2) 0.0275(6) Uani 1 1 d C12 C 0.6103(3) 0.2137(2) 0.2070(2) 0.0301(7) Uani 1 1 d C13 C 0.5205(3) 0.2681(2) 0.17445(18) 0.0251(6) Uani 1 1 d C14 C 0.6772(3) 0.5403(2) 0.38794(18) 0.0265(6) Uani 1 1 d C15 C 0.6470(3) 0.6214(2) 0.35325(19) 0.0284(6) Uani 1 1 d C16 C 0.5502(2) 0.60599(19) 0.29588(18) 0.0235(6) Uani 1 1 d C17 C 0.4579(3) 0.31203(19) 0.45913(17) 0.0248(6) Uani 1 1 d C18 C 0.3442(3) 0.29531(19) 0.44695(18) 0.0263(6) Uani 1 1 d C19 C 0.3013(2) 0.33327(18) 0.37145(17) 0.0221(5) Uani 1 1 d C20 C 0.2259(3) 0.6528(2) 0.2407(2) 0.0298(7) Uani 1 1 d C21 C 0.1046(3) 0.4967(2) 0.2592(2) 0.0304(7) Uani 1 1 d C22 C 0.2831(3) 0.5573(3) 0.38770(19) 0.0313(7) Uani 1 1 d C23 C 0.5150(3) 0.8776(2) 0.0501(2) 0.0309(7) Uani 1 1 d B B 0.5963(3) 0.3787(2) 0.3710(2) 0.0236(6) Uani 1 1 d H1B H 0.662(3) 0.358(2) 0.4204(19) 0.026(8) Uiso 1 1 d H1N H 0.341(3) 0.389(2) -0.0384(19) 0.019(8) Uiso 1 1 d H6 H 0.500(3) 0.390(2) 0.0402(19) 0.024(8) Uiso 1 1 d H5 H 0.524(3) 0.505(2) 0.1378(19) 0.025(8) Uiso 1 1 d H4 H 0.381(3) 0.597(2) 0.152(2) 0.027(9) Uiso 1 1 d H3 H 0.209(3) 0.5840(19) 0.0563(18) 0.016(7) Uiso 1 1 d H8A H 0.094(3) 0.642(3) -0.161(2) 0.042(11) Uiso 1 1 d H8B H 0.193(3) 0.649(3) -0.100(2) 0.051(12) Uiso 1 1 d H9A H 0.281(5) 0.567(3) -0.180(3) 0.086(18) Uiso 1 1 d H9B H 0.183(5) 0.541(3) -0.229(3) 0.075(18) Uiso 1 1 d H10A H 0.131(3) 0.339(2) -0.053(2) 0.035(9) Uiso 1 1 d H10B H 0.030(3) 0.386(3) -0.111(2) 0.048(11) Uiso 1 1 d H10C H 0.052(3) 0.409(2) -0.018(2) 0.030(9) Uiso 1 1 d H11 H 0.715(3) 0.237(2) 0.317(2) 0.030(9) Uiso 1 1 d H12 H 0.633(3) 0.166(2) 0.1817(19) 0.025(8) Uiso 1 1 d H13 H 0.469(3) 0.260(2) 0.126(2) 0.025(8) Uiso 1 1 d H14 H 0.734(3) 0.523(2) 0.4280(19) 0.021(8) Uiso 1 1 d H15 H 0.684(3) 0.672(2) 0.3630(19) 0.024(8) Uiso 1 1 d H16 H 0.509(3) 0.646(2) 0.2601(19) 0.026(8) Uiso 1 1 d H17 H 0.515(2) 0.2963(19) 0.4965(18) 0.014(7) Uiso 1 1 d H18 H 0.304(3) 0.264(2) 0.482(2) 0.025(8) Uiso 1 1 d H19 H 0.230(2) 0.3325(19) 0.3452(17) 0.016(7) Uiso 1 1 d H20A H 0.287(3) 0.683(3) 0.252(2) 0.049(12) Uiso 1 1 d H20B H 0.176(3) 0.684(3) 0.267(2) 0.050(11) Uiso 1 1 d H20C H 0.194(3) 0.657(2) 0.181(2) 0.032(9) Uiso 1 1 d H21A H 0.101(4) 0.438(3) 0.286(3) 0.061(14) Uiso 1 1 d H21C H 0.081(3) 0.493(3) 0.202(2) 0.045(11) Uiso 1 1 d H21B H 0.061(3) 0.537(2) 0.279(2) 0.033(9) Uiso 1 1 d H22A H 0.352(4) 0.580(3) 0.399(3) 0.050(12) Uiso 1 1 d H22B H 0.282(3) 0.508(3) 0.419(2) 0.043(11) Uiso 1 1 d H22C H 0.234(3) 0.598(3) 0.405(2) 0.046(11) 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 W 0.01709(5) 0.01523(5) 0.01482(5) 0.00036(4) 0.00362(3) -0.00025(4) S 0.0227(3) 0.0212(3) 0.0258(3) -0.0011(3) 0.0061(3) 0.0023(3) P 0.0224(3) 0.0186(3) 0.0187(3) -0.0006(2) 0.0046(3) 0.0022(2) F1 0.0858(18) 0.0444(13) 0.0469(13) -0.0028(10) 0.0404(13) -0.0187(12) F2 0.0509(13) 0.0283(10) 0.0558(14) 0.0112(9) 0.0103(11) 0.0101(9) F3 0.0493(13) 0.0372(12) 0.0598(14) -0.0137(10) 0.0094(11) -0.0187(10) O1 0.0354(12) 0.0272(11) 0.0302(11) 0.0014(9) -0.0028(9) 0.0084(9) O2 0.0481(14) 0.0334(12) 0.0171(10) -0.0020(8) 0.0058(9) -0.0030(10) O3 0.0412(13) 0.0289(12) 0.0331(12) -0.0009(10) -0.0064(10) -0.0135(10) O4 0.0251(11) 0.0369(13) 0.0464(14) -0.0151(11) 0.0027(10) 0.0097(9) O5 0.0406(12) 0.0308(11) 0.0257(11) 0.0043(9) 0.0111(9) 0.0070(10) O6 0.0261(11) 0.0286(11) 0.0363(12) -0.0037(9) 0.0044(9) -0.0040(9) N1 0.0275(12) 0.0186(11) 0.0184(11) -0.0022(9) 0.0075(9) 0.0015(9) N2 0.0206(11) 0.0208(11) 0.0179(10) 0.0016(8) 0.0044(8) 0.0026(8) N3 0.0192(11) 0.0257(12) 0.0219(11) 0.0043(9) 0.0042(9) 0.0022(9) N4 0.0220(11) 0.0216(11) 0.0191(11) 0.0014(9) 0.0019(9) -0.0021(9) N5 0.0187(11) 0.0257(12) 0.0209(11) 0.0005(9) 0.0019(9) -0.0021(9) N6 0.0197(10) 0.0180(10) 0.0189(10) 0.0004(8) 0.0032(8) 0.0003(8) N7 0.0213(11) 0.0242(11) 0.0169(10) 0.0030(9) 0.0017(8) -0.0018(9) N8 0.0242(11) 0.0176(11) 0.0181(10) 0.0004(8) 0.0025(9) -0.0010(8) C6 0.0224(13) 0.0246(14) 0.0206(12) 0.0038(11) 0.0099(10) 0.0034(11) C5 0.0204(13) 0.0250(14) 0.0199(12) 0.0035(10) 0.0069(10) -0.0038(10) C4 0.0240(13) 0.0163(13) 0.0177(12) 0.0005(9) 0.0035(10) -0.0014(9) C3 0.0242(13) 0.0160(12) 0.0184(12) 0.0016(9) 0.0022(10) -0.0013(9) C2 0.0254(13) 0.0180(12) 0.0195(12) 0.0018(10) 0.0058(10) 0.0012(10) C7 0.0274(14) 0.0228(13) 0.0210(13) -0.0005(11) 0.0035(11) 0.0012(11) C8 0.059(3) 0.0284(18) 0.039(2) 0.0115(16) -0.0076(18) -0.0060(17) C9 0.042(2) 0.056(3) 0.057(3) 0.028(2) 0.018(2) 0.0059(19) C10 0.0337(17) 0.0311(17) 0.0307(17) 0.0012(14) 0.0006(14) -0.0069(14) C11 0.0230(14) 0.0285(15) 0.0320(16) 0.0064(12) 0.0080(12) 0.0079(12) C12 0.0302(16) 0.0276(15) 0.0343(17) 0.0006(13) 0.0107(13) 0.0075(12) C13 0.0276(14) 0.0265(15) 0.0218(13) 0.0015(11) 0.0061(11) 0.0020(11) C14 0.0214(14) 0.0355(17) 0.0219(14) -0.0062(12) 0.0020(11) -0.0063(11) C15 0.0291(15) 0.0284(15) 0.0277(15) -0.0062(12) 0.0055(12) -0.0097(12) C16 0.0260(14) 0.0210(13) 0.0237(14) -0.0005(11) 0.0055(11) -0.0052(11) C17 0.0341(15) 0.0227(13) 0.0172(12) 0.0032(11) 0.0033(11) 0.0007(12) C18 0.0376(16) 0.0222(14) 0.0213(13) 0.0022(11) 0.0115(12) -0.0024(12) C19 0.0251(14) 0.0196(13) 0.0224(13) -0.0021(10) 0.0069(11) -0.0040(10) C20 0.0369(18) 0.0183(14) 0.0357(18) 0.0012(12) 0.0106(14) 0.0064(13) C21 0.0214(14) 0.0323(17) 0.0376(19) 0.0047(14) 0.0057(13) 0.0029(12) C22 0.0409(19) 0.0329(17) 0.0203(13) -0.0049(13) 0.0062(13) 0.0050(15) C23 0.0385(17) 0.0251(15) 0.0314(16) -0.0031(12) 0.0126(13) -0.0052(13) B 0.0223(15) 0.0276(16) 0.0202(14) 0.0037(12) 0.0021(12) -0.0010(12) 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' F F 0.0171 0.0103 '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' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N8 W N6 95.05(9) N8 W N2 93.36(9) N6 W N2 76.96(8) N8 W C4 93.85(10) N6 W C4 159.18(9) N2 W C4 121.24(9) N8 W N4 178.02(9) N6 W N4 83.77(8) N2 W N4 84.83(8) C4 W N4 87.78(9) N8 W C5 98.16(10) N6 W C5 156.33(10) N2 W C5 82.71(9) C4 W C5 38.54(10) N4 W C5 82.43(9) N8 W P 93.85(8) N6 W P 81.05(6) N2 W P 157.37(6) C4 W P 79.61(7) N4 W P 87.54(6) C5 W P 117.36(8) O6 S O5 116.06(14) O6 S O4 114.28(13) O5 S O4 114.70(14) O6 S C23 102.72(14) O5 S C23 103.31(14) O4 S C23 103.30(15) C21 P C20 101.71(17) C21 P C22 105.04(18) C20 P C22 100.73(17) C21 P W 113.48(12) C20 P W 120.15(12) C22 P W 113.78(12) C7 O1 C8 106.2(3) C9 O2 C7 106.9(3) C6 N1 C2 122.0(2) C13 N2 N3 106.5(2) C13 N2 W 131.18(19) N3 N2 W 121.85(17) C11 N3 N2 109.0(2) C11 N3 B 129.2(2) N2 N3 B 119.9(2) C16 N4 N5 106.1(2) C16 N4 W 133.88(19) N5 N4 W 119.97(17) C14 N5 N4 109.4(2) C14 N5 B 129.2(2) N4 N5 B 121.3(2) C19 N6 N7 106.5(2) C19 N6 W 132.18(19) N7 N6 W 121.25(16) C17 N7 N6 109.0(2) C17 N7 B 129.2(2) N6 N7 B 120.6(2) O3 N8 W 177.7(2) N1 C6 C5 122.0(3) C6 C5 C4 118.8(3) C6 C5 W 112.36(19) C4 C5 W 70.27(14) C3 C4 C5 114.1(2) C3 C4 W 118.91(18) C5 C4 W 71.19(14) C2 C3 C4 122.9(3) C3 C2 N1 119.0(3) C3 C2 C7 126.7(3) N1 C2 C7 114.3(2) O1 C7 O2 106.3(2) O1 C7 C10 109.9(3) O2 C7 C10 108.8(2) O1 C7 C2 110.6(2) O2 C7 C2 108.9(2) C10 C7 C2 112.2(2) O1 C8 C9 104.4(3) O2 C9 C8 106.5(3) N3 C11 C12 108.8(3) C11 C12 C13 105.4(3) N2 C13 C12 110.3(3) N5 C14 C15 108.6(3) C14 C15 C16 105.4(3) N4 C16 C15 110.4(3) N7 C17 C18 109.1(3) C17 C18 C19 104.7(3) N6 C19 C18 110.7(3) F3 C23 F2 107.1(3) F3 C23 F1 107.6(3) F2 C23 F1 107.9(3) F3 C23 S 111.9(2) F2 C23 S 111.0(2) F1 C23 S 111.1(2) N5 B N3 109.6(2) N5 B N7 108.2(2) N3 B N7 105.6(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance W N8 1.774(2) W N6 2.186(2) W N2 2.189(2) W C4 2.226(3) W N4 2.229(2) W C5 2.239(3) W P 2.5179(7) S O6 1.433(2) S O5 1.436(2) S O4 1.442(2) S C23 1.823(3) P C21 1.809(3) P C20 1.812(3) P C22 1.821(3) F1 C23 1.330(4) F2 C23 1.327(4) F3 C23 1.324(4) O1 C7 1.403(3) O1 C8 1.431(4) O2 C9 1.418(5) O2 C7 1.421(3) O3 N8 1.215(3) N1 C6 1.315(4) N1 C2 1.404(3) N2 C13 1.333(4) N2 N3 1.365(3) N3 C11 1.347(4) N3 B 1.546(4) N4 C16 1.338(4) N4 N5 1.366(3) N5 C14 1.345(4) N5 B 1.538(4) N6 C19 1.340(3) N6 N7 1.366(3) N7 C17 1.348(3) N7 B 1.546(4) C6 C5 1.393(4) C5 C4 1.474(4) C4 C3 1.460(4) C3 C2 1.332(4) C2 C7 1.522(4) C7 C10 1.514(4) C8 C9 1.492(6) C11 C12 1.360(5) C12 C13 1.384(4) C14 C15 1.365(4) C15 C16 1.382(4) C17 C18 1.374(4) C18 C19 1.384(4)