# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Prof W Piers' _publ_contact_author_address ; Department of Chemistry University of Calgary 2500 University Drive NW Calgary Alberta T2N 1NY CANADA ; _publ_requested_coeditor_name ' ? ' _publ_contact_author_phone ' (403)220-5746 ' _publ_contact_author_fax ' (403)289-9488 ' _publ_contact_author_email wpiers@ucalgary.ca #------------------------------------------------------------------------------ _publ_section_title ; Cyclic boronium and borenium cations derived from borabenzene-pyridine complexes. ; loop_ _publ_author_name 'I. Ghesner' 'W.E. Piers' 'M. Parvez' 'R. McDonald' #------------------------------------------------------------------------------ data_Compound_[3a]Cl _database_code_depnum_ccdc_archive 'CCDC 264123' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 B N2, C H2 Cl2, Cl' _chemical_formula_sum 'C16 H18 B Cl3 N2' _chemical_formula_weight 355.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4732(13) _cell_length_b 13.5673(17) _cell_length_c 12.5002(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.264(2) _cell_angle_gamma 90.00 _cell_volume 1773.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4122 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.93 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.513 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6666 _exptl_absorpt_correction_T_max 0.8696 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12172 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3620 _reflns_number_gt 2621 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # SOFTWARE # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0438P)^2^+0.7992P] 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 3620 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 N1 N 0.36543(16) 0.08455(13) 0.27210(13) 0.0338(4) Uani 1 1 d . . . N2 N 0.14200(17) 0.13190(13) 0.31986(14) 0.0360(4) Uani 1 1 d . . . C1 C 0.2118(3) -0.05093(17) 0.34924(19) 0.0489(6) Uani 1 1 d . . . H1 H 0.1575 -0.0721 0.2902 0.059 Uiso 1 1 calc R . . C2 C 0.2494(3) -0.11478(19) 0.4264(2) 0.0540(7) Uani 1 1 d . . . H2 H 0.2279 -0.1823 0.4160 0.065 Uiso 1 1 calc R . . C3 C 0.3203(3) -0.0878(2) 0.5239(3) 0.0747(9) Uani 1 1 d . . . H3A H 0.4034 -0.1227 0.5255 0.090 Uiso 1 1 calc R . . H3B H 0.2732 -0.1131 0.5846 0.090 Uiso 1 1 calc R . . C4 C 0.3462(2) 0.01592(19) 0.54323(18) 0.0467(6) Uani 1 1 d . . . H4 H 0.3856 0.0343 0.6106 0.056 Uiso 1 1 calc R . . C5 C 0.3186(2) 0.08620(18) 0.47294(17) 0.0429(5) Uani 1 1 d . . . H5 H 0.3348 0.1531 0.4918 0.051 Uiso 1 1 calc R . . C11 C 0.4145(2) 0.01465(18) 0.21062(17) 0.0424(5) Uani 1 1 d . . . H11 H 0.3810 -0.0503 0.2126 0.051 Uiso 1 1 calc R . . C12 C 0.5120(2) 0.0346(2) 0.14493(19) 0.0509(6) Uani 1 1 d . . . H12 H 0.5455 -0.0164 0.1027 0.061 Uiso 1 1 calc R . . C13 C 0.5608(2) 0.1279(2) 0.1403(2) 0.0531(6) Uani 1 1 d . . . H13 H 0.6285 0.1426 0.0954 0.064 Uiso 1 1 calc R . . C14 C 0.5093(2) 0.2003(2) 0.2027(2) 0.0507(6) Uani 1 1 d . . . H14 H 0.5405 0.2660 0.2004 0.061 Uiso 1 1 calc R . . C15 C 0.4128(2) 0.17686(17) 0.26804(18) 0.0409(5) Uani 1 1 d . . . H15 H 0.3785 0.2268 0.3114 0.049 Uiso 1 1 calc R . . C21 C 0.1010(2) 0.13782(17) 0.21629(18) 0.0432(5) Uani 1 1 d . . . H21 H 0.1448 0.1017 0.1645 0.052 Uiso 1 1 calc R . . C22 C -0.0025(2) 0.19452(19) 0.1829(2) 0.0529(6) Uani 1 1 d . . . H22 H -0.0293 0.1984 0.1092 0.063 Uiso 1 1 calc R . . C23 C -0.0664(2) 0.2455(2) 0.2585(3) 0.0604(7) Uani 1 1 d . . . H23 H -0.1382 0.2853 0.2375 0.072 Uiso 1 1 calc R . . C24 C -0.0259(3) 0.2385(2) 0.3642(3) 0.0657(8) Uani 1 1 d . . . H24 H -0.0701 0.2724 0.4174 0.079 Uiso 1 1 calc R . . C25 C 0.0795(2) 0.1818(2) 0.3924(2) 0.0524(6) Uani 1 1 d . . . H25 H 0.1086 0.1781 0.4657 0.063 Uiso 1 1 calc R . . B B 0.2583(3) 0.05995(19) 0.35696(19) 0.0380(6) Uani 1 1 d . . . Cl1 Cl 0.20233(5) -0.13366(4) 0.05930(4) 0.04191(16) Uani 1 1 d . . . Cl1S Cl -0.15330(7) -0.03818(5) 0.25336(5) 0.0597(2) Uani 1 1 d . . . Cl2S Cl -0.18806(8) -0.14918(5) 0.05608(6) 0.0698(2) Uani 1 1 d . . . C1S C -0.1056(2) -0.05099(17) 0.12100(19) 0.0468(6) Uani 1 1 d . . . H1SA H -0.1236 0.0109 0.0810 0.056 Uiso 1 1 calc R . . H1SB H -0.0124 -0.0634 0.1221 0.056 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 N1 0.0371(10) 0.0343(10) 0.0291(9) -0.0021(7) -0.0060(7) 0.0048(8) N2 0.0367(10) 0.0357(10) 0.0354(9) -0.0009(8) 0.0003(8) -0.0046(8) C1 0.0687(17) 0.0384(13) 0.0386(13) -0.0002(10) -0.0057(11) -0.0067(12) C2 0.0632(16) 0.0385(14) 0.0587(16) 0.0090(12) -0.0098(13) -0.0081(12) C3 0.075(2) 0.0593(19) 0.086(2) 0.0241(16) -0.0285(17) -0.0092(16) C4 0.0428(13) 0.0600(16) 0.0365(12) 0.0059(11) -0.0036(10) -0.0027(12) C5 0.0526(14) 0.0419(13) 0.0338(12) -0.0045(10) -0.0006(10) 0.0007(11) C11 0.0472(13) 0.0419(13) 0.0373(12) -0.0079(10) -0.0049(10) 0.0088(11) C12 0.0500(15) 0.0584(17) 0.0437(14) -0.0113(12) -0.0020(11) 0.0179(13) C13 0.0391(13) 0.0773(19) 0.0433(13) 0.0004(13) 0.0048(11) 0.0078(13) C14 0.0464(14) 0.0530(15) 0.0528(15) 0.0001(12) 0.0049(11) -0.0056(12) C15 0.0438(13) 0.0400(13) 0.0387(12) -0.0047(10) 0.0009(10) 0.0021(10) C21 0.0436(13) 0.0470(14) 0.0386(12) 0.0033(11) -0.0002(10) -0.0008(11) C22 0.0431(14) 0.0546(16) 0.0597(16) 0.0125(13) -0.0080(12) -0.0028(12) C23 0.0389(14) 0.0519(16) 0.089(2) 0.0009(15) -0.0058(14) 0.0051(12) C24 0.0425(15) 0.074(2) 0.080(2) -0.0239(16) 0.0012(14) 0.0096(14) C25 0.0454(14) 0.0642(17) 0.0478(14) -0.0124(13) 0.0034(11) 0.0000(12) B 0.0470(15) 0.0356(13) 0.0310(12) 0.0001(11) -0.0007(10) 0.0005(11) Cl1 0.0405(3) 0.0452(3) 0.0401(3) 0.0007(2) 0.0033(2) 0.0011(2) Cl1S 0.0637(4) 0.0575(4) 0.0590(4) -0.0025(3) 0.0125(3) 0.0056(3) Cl2S 0.0762(5) 0.0645(5) 0.0706(5) -0.0152(4) 0.0211(4) -0.0259(4) C1S 0.0462(14) 0.0398(13) 0.0555(15) 0.0016(11) 0.0112(11) -0.0033(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.341(3) . ? N1 C15 1.349(3) . ? N1 B 1.622(3) . ? N2 C25 1.333(3) . ? N2 C21 1.343(3) . ? N2 B 1.609(3) . ? C1 C2 1.339(3) . ? C1 B 1.583(3) . ? C2 C3 1.439(4) . ? C3 C4 1.450(4) . ? C4 C5 1.318(3) . ? C5 B 1.588(3) . ? C11 C12 1.373(3) . ? C12 C13 1.368(4) . ? C13 C14 1.383(4) . ? C14 C15 1.372(3) . ? C21 C22 1.374(3) . ? C22 C23 1.376(4) . ? C23 C24 1.367(4) . ? C24 C25 1.375(4) . ? Cl1S C1S 1.764(2) . ? Cl2S C1S 1.760(2) . ? 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 N1 C15 118.77(19) . . ? C11 N1 B 122.08(19) . . ? C15 N1 B 119.01(17) . . ? C25 N2 C21 118.9(2) . . ? C25 N2 B 120.36(19) . . ? C21 N2 B 120.64(18) . . ? C2 C1 B 119.6(2) . . ? C1 C2 C3 124.2(2) . . ? C2 C3 C4 118.1(2) . . ? C5 C4 C3 124.0(2) . . ? C4 C5 B 120.5(2) . . ? N1 C11 C12 121.7(2) . . ? C13 C12 C11 120.0(2) . . ? C12 C13 C14 118.4(2) . . ? C15 C14 C13 119.7(2) . . ? N1 C15 C14 121.5(2) . . ? N2 C21 C22 122.0(2) . . ? C21 C22 C23 118.7(2) . . ? C24 C23 C22 119.5(3) . . ? C23 C24 C25 119.2(3) . . ? N2 C25 C24 121.9(2) . . ? C1 B C5 111.95(19) . . ? C1 B N2 109.50(19) . . ? C5 B N2 112.46(18) . . ? C1 B N1 112.19(19) . . ? C5 B N1 107.29(18) . . ? N2 B N1 103.13(16) . . ? Cl2S C1S Cl1S 110.45(13) . . ? 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 B C1 C2 C3 6.7(4) . . . . ? C1 C2 C3 C4 3.9(5) . . . . ? C2 C3 C4 C5 -6.1(5) . . . . ? C3 C4 C5 B -2.7(4) . . . . ? C15 N1 C11 C12 0.6(3) . . . . ? B N1 C11 C12 -175.0(2) . . . . ? N1 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? C11 N1 C15 C14 0.0(3) . . . . ? B N1 C15 C14 175.8(2) . . . . ? C13 C14 C15 N1 -0.8(4) . . . . ? C25 N2 C21 C22 0.7(3) . . . . ? B N2 C21 C22 176.4(2) . . . . ? N2 C21 C22 C23 -0.8(4) . . . . ? C21 C22 C23 C24 -0.1(4) . . . . ? C22 C23 C24 C25 1.1(4) . . . . ? C21 N2 C25 C24 0.4(4) . . . . ? B N2 C25 C24 -175.3(2) . . . . ? C23 C24 C25 N2 -1.3(4) . . . . ? C2 C1 B C5 -14.0(3) . . . . ? C2 C1 B N2 -139.4(2) . . . . ? C2 C1 B N1 106.7(3) . . . . ? C4 C5 B C1 12.1(3) . . . . ? C4 C5 B N2 135.9(2) . . . . ? C4 C5 B N1 -111.4(2) . . . . ? C25 N2 B C1 103.8(2) . . . . ? C21 N2 B C1 -71.9(2) . . . . ? C25 N2 B C5 -21.3(3) . . . . ? C21 N2 B C5 163.0(2) . . . . ? C25 N2 B N1 -136.6(2) . . . . ? C21 N2 B N1 47.7(2) . . . . ? C11 N1 B C1 -5.5(3) . . . . ? C15 N1 B C1 178.91(19) . . . . ? C11 N1 B C5 117.9(2) . . . . ? C15 N1 B C5 -57.7(2) . . . . ? C11 N1 B N2 -123.20(19) . . . . ? C15 N1 B N2 61.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.301 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.048 #===END data_4c _database_code_depnum_ccdc_archive 'CCDC 264124' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #----------------------------------------------------------------------------- #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 B Cl N' _chemical_formula_weight 205.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.967(3) _cell_length_b 11.280(6) _cell_length_c 13.635(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1071.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2441 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9400 _exptl_absorpt_correction_T_max 0.9487 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2441 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1423 _reflns_number_gt 1205 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0330P)^2^+0.2340P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.35(10) _refine_ls_number_reflns 1423 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 Cl1 Cl 0.57869(9) -0.04942(5) 0.84531(5) 0.03786(18) Uani 1 1 d . . . N1 N 0.8055(3) 0.13493(16) 0.91579(14) 0.0278(4) Uani 1 1 d . . . C1 C 0.8112(4) 0.0829(2) 1.00466(18) 0.0335(6) Uani 1 1 d . . . H1 H 0.8052 -0.0011 1.0084 0.040 Uiso 1 1 calc R . . C2 C 0.8252(4) 0.1467(3) 1.0899(2) 0.0404(6) Uani 1 1 d . . . H2 H 0.8289 0.1076 1.1516 0.048 Uiso 1 1 calc R . . C3 C 0.8339(4) 0.2694(2) 1.0846(2) 0.0380(6) Uani 1 1 d . . . H3 H 0.8406 0.3157 1.1427 0.046 Uiso 1 1 calc R . . C4 C 0.8327(4) 0.3228(2) 0.9942(2) 0.0384(6) Uani 1 1 d . . . H4 H 0.8409 0.4066 0.9891 0.046 Uiso 1 1 calc R . . C5 C 0.8195(4) 0.2544(2) 0.9111(2) 0.0322(6) Uani 1 1 d . . . H5 H 0.8201 0.2920 0.8488 0.039 Uiso 1 1 calc R . . C6 C 0.7356(4) 0.1365(2) 0.72586(19) 0.0369(6) Uani 1 1 d . . . H6 H 0.6107 0.1698 0.7211 0.044 Uiso 1 1 calc R . . C7 C 0.8654(4) 0.1584(2) 0.6553(2) 0.0392(6) Uani 1 1 d . . . H7 H 0.8281 0.2071 0.6018 0.047 Uiso 1 1 calc R . . C8 C 1.0617(4) 0.1113(2) 0.6566(2) 0.0385(6) Uani 1 1 d . . . C9 C 1.1151(4) 0.0310(2) 0.72402(19) 0.0384(6) Uani 1 1 d . . . H9 H 1.2443 0.0040 0.7230 0.046 Uiso 1 1 calc R . . C10 C 0.9841(4) -0.0185(2) 0.8007(2) 0.0365(6) Uani 1 1 d . . . H10A H 1.0544 -0.0219 0.8637 0.044 Uiso 1 1 calc R . . H10B H 0.9502 -0.1008 0.7823 0.044 Uiso 1 1 calc R . . C11 C 1.1968(5) 0.1556(3) 0.5784(2) 0.0584(9) Uani 1 1 d . . . H11A H 1.3209 0.1154 0.5850 0.070 Uiso 1 1 calc R . . H11B H 1.2148 0.2413 0.5859 0.070 Uiso 1 1 calc R . . H11C H 1.1426 0.1388 0.5136 0.070 Uiso 1 1 calc R . . B1 B 0.7886(4) 0.0557(2) 0.81681(18) 0.0306(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0423(3) 0.0341(3) 0.0371(3) -0.0020(3) 0.0012(3) -0.0048(3) N1 0.0308(10) 0.0264(10) 0.0262(10) 0.0019(8) 0.0009(9) 0.0023(9) C1 0.0405(13) 0.0326(13) 0.0275(13) 0.0038(10) -0.0028(11) 0.0002(11) C2 0.0429(15) 0.0498(16) 0.0284(13) -0.0018(12) -0.0002(12) -0.0021(14) C3 0.0343(14) 0.0446(15) 0.0351(15) -0.0140(12) -0.0016(12) 0.0000(12) C4 0.0383(13) 0.0307(13) 0.0462(16) -0.0058(12) -0.0014(13) -0.0013(11) C5 0.0327(14) 0.0287(12) 0.0353(14) 0.0028(11) 0.0006(12) -0.0007(10) C6 0.0457(14) 0.0327(13) 0.0324(13) 0.0013(11) -0.0058(12) 0.0034(12) C7 0.0610(16) 0.0321(12) 0.0245(12) 0.0039(12) -0.0063(13) -0.0051(12) C8 0.0481(14) 0.0388(13) 0.0284(12) -0.0093(12) 0.0045(14) -0.0163(12) C9 0.0383(14) 0.0419(15) 0.0349(13) -0.0118(12) 0.0011(11) -0.0022(12) C10 0.0411(14) 0.0356(13) 0.0327(13) 0.0003(11) -0.0003(11) 0.0053(11) C11 0.076(2) 0.0581(19) 0.0416(17) -0.0079(15) 0.0167(17) -0.0317(18) B1 0.0387(14) 0.0286(13) 0.0245(13) -0.0011(12) 0.0005(11) -0.0002(13) 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 Cl1 B1 1.922(3) . ? N1 C1 1.347(3) . ? N1 C5 1.353(3) . ? N1 B1 1.623(3) . ? C1 C2 1.371(4) . ? C2 C3 1.387(4) . ? C3 C4 1.372(4) . ? C4 C5 1.373(4) . ? C6 C7 1.343(4) . ? C6 B1 1.582(4) . ? C7 C8 1.467(4) . ? C8 C9 1.343(4) . ? C8 C11 1.507(4) . ? C9 C10 1.496(4) . ? C10 B1 1.614(4) . ? 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 C1 N1 C5 118.3(2) . . ? C1 N1 B1 120.70(19) . . ? C5 N1 B1 121.0(2) . . ? N1 C1 C2 122.5(2) . . ? C1 C2 C3 118.9(3) . . ? C4 C3 C2 119.0(2) . . ? C3 C4 C5 119.7(2) . . ? N1 C5 C4 121.7(3) . . ? C7 C6 B1 120.7(2) . . ? C6 C7 C8 123.5(2) . . ? C9 C8 C7 120.7(2) . . ? C9 C8 C11 122.3(3) . . ? C7 C8 C11 117.0(3) . . ? C8 C9 C10 124.1(2) . . ? C9 C10 B1 114.6(2) . . ? C6 B1 C10 112.9(2) . . ? C6 B1 N1 110.6(2) . . ? C10 B1 N1 109.72(19) . . ? C6 B1 Cl1 109.64(18) . . ? C10 B1 Cl1 110.47(17) . . ? N1 B1 Cl1 103.12(15) . . ? 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 C5 N1 C1 C2 1.8(4) . . . . ? B1 N1 C1 C2 -179.9(2) . . . . ? N1 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C1 N1 C5 C4 -2.1(4) . . . . ? B1 N1 C5 C4 179.6(2) . . . . ? C3 C4 C5 N1 0.7(4) . . . . ? B1 C6 C7 C8 -0.2(4) . . . . ? C6 C7 C8 C9 7.9(4) . . . . ? C6 C7 C8 C11 -173.0(2) . . . . ? C7 C8 C9 C10 1.2(4) . . . . ? C11 C8 C9 C10 -177.8(2) . . . . ? C8 C9 C10 B1 -15.8(4) . . . . ? C7 C6 B1 C10 -14.1(3) . . . . ? C7 C6 B1 N1 109.2(3) . . . . ? C7 C6 B1 Cl1 -137.7(2) . . . . ? C9 C10 B1 C6 21.0(3) . . . . ? C9 C10 B1 N1 -102.9(2) . . . . ? C9 C10 B1 Cl1 144.11(19) . . . . ? C1 N1 B1 C6 166.6(2) . . . . ? C5 N1 B1 C6 -15.1(3) . . . . ? C1 N1 B1 C10 -68.2(3) . . . . ? C5 N1 B1 C10 110.0(2) . . . . ? C1 N1 B1 Cl1 49.5(2) . . . . ? C5 N1 B1 Cl1 -132.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.190 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.041 # start Validation Reply Form #_vrf_PUBL012_GLOBAL #; #PROBLEM: _publ_section_abstract is missing. #RESPONSE: Please refer to the article #; #_vrf_PLAT035_Compound_I #; #PROBLEM: No _chemical_absolute_configuration info given . ? #RESPONSE: An absolute structure was not established in this analysis #; #_vrf_PLAT761_Compound_I #; #PROBLEM: CIF Contains no X-H Bonds ...................... ? #RESPONSE: IOncluded at geometric positions #; #_vrf_PLAT762_Compound_I #; #PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles .......... ? #RESPONSE: The same as above #; #===END