# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_riv1224 _database_code_depnum_ccdc_archive 'CCDC 902241' #TrackingRef '16669_web_deposit_cif_file_0_EricRivard_1357602407.CCDC902241_Dalton_Rivard_Jan2013.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1 _chemical_melting_point ? _chemical_formula_moiety 'C28 H45 B2 N3, C7 H8' _chemical_formula_sum 'C35 H53 B2 N3' _chemical_formula_weight 537.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5000(2) _cell_length_b 13.8866(2) _cell_length_c 17.5606(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.3528(6) _cell_angle_gamma 90.00 _cell_volume 3478.36(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9704 _cell_measurement_theta_min 3.65 _cell_measurement_theta_max 70.20 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.026 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.435 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8623 _exptl_absorpt_correction_T_max 0.9123 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23523 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_unetl/netl 0.0143 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 70.74 _reflns_number_total 6657 _reflns_number_gt 6123 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.8916P] 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 6657 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1445 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 N1 N 0.22049(7) 0.29869(7) 0.16838(6) 0.0324(2) Uani 1 1 d . . . N2 N 0.35777(7) 0.32804(7) 0.14470(6) 0.0318(2) Uani 1 1 d . . . N3 N 0.15588(8) 0.49531(9) 0.06311(7) 0.0426(3) Uani 1 1 d . . . H3N H 0.1066(13) 0.4686(13) 0.0854(10) 0.053(5) Uiso 1 1 d . . . C1 C 0.26624(8) 0.34984(8) 0.12075(7) 0.0307(3) Uani 1 1 d . . . C2 C 0.28302(9) 0.24604(9) 0.22124(7) 0.0380(3) Uani 1 1 d . . . H2 H 0.2681 0.2050 0.2606 0.046 Uiso 1 1 calc R . . C3 C 0.36874(9) 0.26409(9) 0.20613(7) 0.0382(3) Uani 1 1 d . . . H3 H 0.4262 0.2379 0.2326 0.046 Uiso 1 1 calc R . . C4 C 0.11050(12) 0.53960(14) -0.01101(10) 0.0588(4) Uani 1 1 d . . . H4A H 0.0692 0.5919 -0.0006 0.071 Uiso 1 1 calc R . . H4B H 0.0736 0.4908 -0.0434 0.071 Uiso 1 1 calc R . . H4C H 0.1587 0.5653 -0.0380 0.071 Uiso 1 1 calc R . . C11 C 0.11981(9) 0.29205(9) 0.16130(7) 0.0351(3) Uani 1 1 d . . . C12 C 0.07594(10) 0.34394(9) 0.21311(8) 0.0397(3) Uani 1 1 d . . . C13 C -0.02096(10) 0.33317(10) 0.20566(10) 0.0491(4) Uani 1 1 d . . . H13 H -0.0533 0.3674 0.2396 0.059 Uiso 1 1 calc R . . C14 C -0.07042(10) 0.27405(12) 0.15023(10) 0.0538(4) Uani 1 1 d . . . H14 H -0.1364 0.2681 0.1461 0.065 Uiso 1 1 calc R . . C15 C -0.02500(11) 0.22311(12) 0.10034(9) 0.0511(4) Uani 1 1 d . . . H15 H -0.0603 0.1826 0.0623 0.061 Uiso 1 1 calc R . . C16 C 0.07153(10) 0.23014(10) 0.10488(8) 0.0426(3) Uani 1 1 d . . . C17 C 0.13008(11) 0.40579(10) 0.27721(9) 0.0475(3) Uani 1 1 d . . . H17 H 0.1934 0.4184 0.2644 0.057 Uiso 1 1 calc R . . C18 C 0.08269(15) 0.50320(13) 0.28390(14) 0.0717(5) Uani 1 1 d . . . H18A H 0.1203 0.5410 0.3253 0.086 Uiso 1 1 calc R . . H18B H 0.0200 0.4928 0.2959 0.086 Uiso 1 1 calc R . . H18C H 0.0775 0.5380 0.2348 0.086 Uiso 1 1 calc R . . C19 C 0.14386(16) 0.35167(14) 0.35402(10) 0.0680(5) Uani 1 1 d . . . H19A H 0.1761 0.2907 0.3489 0.082 Uiso 1 1 calc R . . H19B H 0.0826 0.3387 0.3681 0.082 Uiso 1 1 calc R . . H19C H 0.1816 0.3909 0.3944 0.082 Uiso 1 1 calc R . . C20 C 0.12215(12) 0.16883(12) 0.05333(9) 0.0562(4) Uani 1 1 d . . . H20 H 0.1839 0.2002 0.0521 0.067 Uiso 1 1 calc R . . C21 C 0.06963(19) 0.1632(2) -0.02968(12) 0.0949(8) Uani 1 1 d . . . H21A H 0.0573 0.2284 -0.0503 0.114 Uiso 1 1 calc R . . H21B H 0.0101 0.1294 -0.0309 0.114 Uiso 1 1 calc R . . H21C H 0.1077 0.1282 -0.0613 0.114 Uiso 1 1 calc R . . C22 C 0.14232(18) 0.06853(15) 0.08808(15) 0.0829(7) Uani 1 1 d . . . H22A H 0.1771 0.0744 0.1412 0.099 Uiso 1 1 calc R . . H22B H 0.1798 0.0320 0.0568 0.099 Uiso 1 1 calc R . . H22C H 0.0830 0.0348 0.0885 0.099 Uiso 1 1 calc R . . C31 C 0.43546(8) 0.35781(9) 0.10853(7) 0.0326(3) Uani 1 1 d . . . C32 C 0.48876(9) 0.43724(9) 0.13907(7) 0.0355(3) Uani 1 1 d . . . C33 C 0.56555(10) 0.46108(10) 0.10495(8) 0.0432(3) Uani 1 1 d . . . H33 H 0.6034 0.5147 0.1240 0.052 Uiso 1 1 calc R . . C34 C 0.58746(10) 0.40827(11) 0.04415(9) 0.0464(3) Uani 1 1 d . . . H34 H 0.6399 0.4260 0.0216 0.056 Uiso 1 1 calc R . . C35 C 0.53376(10) 0.33000(11) 0.01588(8) 0.0447(3) Uani 1 1 d . . . H35 H 0.5499 0.2941 -0.0258 0.054 Uiso 1 1 calc R . . C36 C 0.45612(9) 0.30251(10) 0.04735(7) 0.0385(3) Uani 1 1 d . . . C37 C 0.46645(9) 0.49386(10) 0.20753(8) 0.0401(3) Uani 1 1 d . . . H37 H 0.4010 0.4774 0.2134 0.048 Uiso 1 1 calc R . . C38 C 0.47089(16) 0.60194(11) 0.19595(11) 0.0642(5) Uani 1 1 d . . . H38A H 0.4291 0.6199 0.1478 0.077 Uiso 1 1 calc R . . H38B H 0.5353 0.6207 0.1930 0.077 Uiso 1 1 calc R . . H38C H 0.4511 0.6350 0.2396 0.077 Uiso 1 1 calc R . . C39 C 0.53157(15) 0.46373(16) 0.28160(10) 0.0679(5) Uani 1 1 d . . . H39A H 0.5274 0.3939 0.2884 0.081 Uiso 1 1 calc R . . H39B H 0.5130 0.4966 0.3259 0.081 Uiso 1 1 calc R . . H39C H 0.5962 0.4813 0.2782 0.081 Uiso 1 1 calc R . . C40 C 0.39837(10) 0.21545(11) 0.01511(9) 0.0483(3) Uani 1 1 d . . . H40 H 0.3473 0.2068 0.0459 0.058 Uiso 1 1 calc R . . C41 C 0.35269(15) 0.23163(15) -0.06887(12) 0.0745(6) Uani 1 1 d . . . H41A H 0.3157 0.2911 -0.0730 0.089 Uiso 1 1 calc R . . H41B H 0.3116 0.1772 -0.0869 0.089 Uiso 1 1 calc R . . H41C H 0.4014 0.2371 -0.1008 0.089 Uiso 1 1 calc R . . C42 C 0.45755(13) 0.12376(12) 0.02345(11) 0.0600(4) Uani 1 1 d . . . H42A H 0.4877 0.1157 0.0777 0.072 Uiso 1 1 calc R . . H42B H 0.5057 0.1286 -0.0091 0.072 Uiso 1 1 calc R . . H42C H 0.4172 0.0681 0.0071 0.072 Uiso 1 1 calc R . . B1 B 0.22177(10) 0.41178(11) 0.04537(8) 0.0366(3) Uani 1 1 d . . . H1BA H 0.2794(12) 0.4400(12) 0.0183(9) 0.048(4) Uiso 1 1 d . . . H1BB H 0.1774(12) 0.3602(13) 0.0023(10) 0.052(4) Uiso 1 1 d . . . B2 B 0.20409(16) 0.57722(13) 0.12074(12) 0.0571(5) Uani 1 1 d . . . H2BA H 0.2571(15) 0.6164(16) 0.0873(12) 0.079(6) Uiso 1 1 d . . . H2BB H 0.2369(12) 0.5389(12) 0.1774(10) 0.053(4) Uiso 1 1 d . . . H2BC H 0.1481(15) 0.6289(16) 0.1314(12) 0.078(6) Uiso 1 1 d . . . C1S C 0.70366(13) 0.10550(19) 0.16122(11) 0.0732(6) Uani 1 1 d . . . C2S C 0.67457(16) 0.19508(19) 0.18437(17) 0.0916(8) Uani 1 1 d . . . H2S H 0.6690 0.2488 0.1504 0.110 Uiso 1 1 calc R . . C3S C 0.65356(18) 0.2038(3) 0.2600(2) 0.1151(12) Uani 1 1 d . . . H3S H 0.6328 0.2636 0.2771 0.138 Uiso 1 1 calc R . . C4S C 0.6634(3) 0.1260(4) 0.30762(19) 0.1337(16) Uani 1 1 d . . . H4S H 0.6530 0.1331 0.3592 0.160 Uiso 1 1 calc R . . C5S C 0.6863(2) 0.0436(4) 0.2848(2) 0.1186(12) Uani 1 1 d . . . H5S H 0.6884 -0.0101 0.3186 0.142 Uiso 1 1 calc R . . C6S C 0.70730(15) 0.03142(19) 0.2150(2) 0.0937(8) Uani 1 1 d . . . H6S H 0.7257 -0.0309 0.2010 0.112 Uiso 1 1 calc R . . C7S C 0.7299(2) 0.0878(4) 0.08499(18) 0.169(2) Uani 1 1 d . . . H7SA H 0.6949 0.0323 0.0604 0.203 Uiso 1 1 calc R . . H7SB H 0.7973 0.0747 0.0918 0.203 Uiso 1 1 calc R . . H7SC H 0.7149 0.1448 0.0521 0.203 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 0.0380(5) 0.0291(5) 0.0326(5) 0.0009(4) 0.0130(4) -0.0036(4) N2 0.0355(5) 0.0295(5) 0.0320(5) 0.0017(4) 0.0104(4) -0.0017(4) N3 0.0427(6) 0.0433(6) 0.0420(6) 0.0064(5) 0.0080(5) 0.0039(5) C1 0.0357(6) 0.0270(5) 0.0313(6) -0.0028(4) 0.0115(5) -0.0040(4) C2 0.0463(7) 0.0338(6) 0.0359(6) 0.0066(5) 0.0126(5) -0.0017(5) C3 0.0422(7) 0.0355(6) 0.0374(6) 0.0073(5) 0.0087(5) 0.0009(5) C4 0.0582(9) 0.0655(10) 0.0510(9) 0.0131(8) 0.0049(7) 0.0167(8) C11 0.0378(6) 0.0314(6) 0.0387(6) 0.0048(5) 0.0138(5) -0.0044(5) C12 0.0447(7) 0.0298(6) 0.0489(7) 0.0043(5) 0.0201(6) -0.0013(5) C13 0.0462(8) 0.0388(7) 0.0681(10) 0.0076(7) 0.0261(7) 0.0036(6) C14 0.0367(7) 0.0526(9) 0.0726(10) 0.0144(8) 0.0115(7) -0.0031(6) C15 0.0468(8) 0.0535(8) 0.0521(8) 0.0047(7) 0.0060(6) -0.0148(6) C16 0.0475(7) 0.0411(7) 0.0411(7) 0.0016(6) 0.0132(6) -0.0109(6) C17 0.0563(8) 0.0385(7) 0.0546(8) -0.0090(6) 0.0284(7) -0.0088(6) C18 0.0782(12) 0.0455(9) 0.1017(15) -0.0234(9) 0.0434(11) -0.0062(8) C19 0.0948(14) 0.0652(11) 0.0488(9) -0.0116(8) 0.0256(9) -0.0206(10) C20 0.0626(9) 0.0577(9) 0.0538(9) -0.0195(7) 0.0252(7) -0.0250(8) C21 0.1048(17) 0.125(2) 0.0582(11) -0.0394(13) 0.0236(11) -0.0436(15) C22 0.1015(16) 0.0542(10) 0.1070(17) -0.0211(11) 0.0562(14) -0.0059(10) C31 0.0324(6) 0.0330(6) 0.0338(6) 0.0045(5) 0.0097(5) -0.0002(5) C32 0.0360(6) 0.0336(6) 0.0369(6) 0.0039(5) 0.0068(5) -0.0004(5) C33 0.0392(7) 0.0395(7) 0.0517(8) 0.0051(6) 0.0109(6) -0.0066(5) C34 0.0415(7) 0.0507(8) 0.0516(8) 0.0112(6) 0.0206(6) -0.0019(6) C35 0.0465(7) 0.0511(8) 0.0407(7) 0.0015(6) 0.0193(6) 0.0029(6) C36 0.0400(7) 0.0394(7) 0.0378(6) 0.0000(5) 0.0118(5) 0.0004(5) C37 0.0410(7) 0.0377(7) 0.0418(7) -0.0037(5) 0.0079(5) -0.0030(5) C38 0.0978(14) 0.0393(8) 0.0576(9) -0.0086(7) 0.0199(9) -0.0058(8) C39 0.0780(12) 0.0826(13) 0.0410(8) -0.0040(8) 0.0054(8) 0.0215(10) C40 0.0477(8) 0.0484(8) 0.0525(8) -0.0154(6) 0.0188(6) -0.0056(6) C41 0.0787(13) 0.0635(11) 0.0714(12) -0.0218(9) -0.0134(10) 0.0044(9) C42 0.0687(10) 0.0442(8) 0.0696(10) -0.0027(7) 0.0195(8) -0.0042(7) B1 0.0396(7) 0.0373(7) 0.0344(7) 0.0044(6) 0.0105(6) -0.0015(6) B2 0.0737(12) 0.0381(9) 0.0564(10) -0.0032(7) 0.0036(9) 0.0043(8) C1S 0.0487(9) 0.1071(17) 0.0634(11) -0.0193(11) 0.0085(8) -0.0240(10) C2S 0.0683(13) 0.0847(15) 0.1079(19) 0.0215(14) -0.0218(13) -0.0062(11) C3S 0.0662(14) 0.138(3) 0.139(3) -0.069(2) 0.0116(16) 0.0105(15) C4S 0.124(3) 0.201(4) 0.0728(17) -0.010(2) 0.0088(17) -0.076(3) C5S 0.097(2) 0.159(3) 0.092(2) 0.026(2) -0.0039(16) -0.049(2) C6S 0.0581(12) 0.0748(14) 0.145(3) 0.0024(15) 0.0102(13) -0.0085(10) C7S 0.109(2) 0.311(6) 0.097(2) -0.087(3) 0.0435(18) -0.105(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3578(15) . ? N1 C2 1.3841(17) . ? N1 C11 1.4456(16) . ? N2 C1 1.3526(16) . ? N2 C3 1.3843(16) . ? N2 C31 1.4492(15) . ? N3 C4 1.4825(18) . ? N3 B1 1.5692(19) . ? N3 B2 1.598(2) . ? C1 B1 1.6128(18) . ? C2 C3 1.3405(18) . ? C11 C12 1.4000(18) . ? C11 C16 1.4005(19) . ? C12 C13 1.396(2) . ? C12 C17 1.518(2) . ? C13 C14 1.373(2) . ? C14 C15 1.382(2) . ? C15 C16 1.391(2) . ? C16 C20 1.524(2) . ? C17 C19 1.526(2) . ? C17 C18 1.531(2) . ? C20 C21 1.520(3) . ? C20 C22 1.528(3) . ? C31 C36 1.3962(18) . ? C31 C32 1.3974(18) . ? C32 C33 1.3957(18) . ? C32 C37 1.5192(18) . ? C33 C34 1.379(2) . ? C34 C35 1.377(2) . ? C35 C36 1.3936(19) . ? C36 C40 1.5207(19) . ? C37 C38 1.517(2) . ? C37 C39 1.522(2) . ? C40 C41 1.521(2) . ? C40 C42 1.528(2) . ? C1S C6S 1.391(4) . ? C1S C2S 1.397(4) . ? C1S C7S 1.476(3) . ? C2S C3S 1.420(4) . ? C3S C4S 1.358(5) . ? C4S C5S 1.276(6) . ? C5S C6S 1.326(5) . ? 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 C2 110.84(10) . . ? C1 N1 C11 125.31(10) . . ? C2 N1 C11 123.62(10) . . ? C1 N2 C3 110.78(10) . . ? C1 N2 C31 126.62(10) . . ? C3 N2 C31 122.35(10) . . ? C4 N3 B1 108.81(11) . . ? C4 N3 B2 109.60(13) . . ? B1 N3 B2 116.07(12) . . ? N2 C1 N1 104.61(10) . . ? N2 C1 B1 126.85(10) . . ? N1 C1 B1 128.10(11) . . ? C3 C2 N1 106.70(11) . . ? C2 C3 N2 107.07(11) . . ? C12 C11 C16 123.23(12) . . ? C12 C11 N1 118.75(11) . . ? C16 C11 N1 117.95(11) . . ? C13 C12 C11 116.83(13) . . ? C13 C12 C17 120.53(13) . . ? C11 C12 C17 122.58(12) . . ? C14 C13 C12 121.29(14) . . ? C13 C14 C15 120.53(14) . . ? C14 C15 C16 121.14(14) . . ? C15 C16 C11 116.97(13) . . ? C15 C16 C20 120.92(13) . . ? C11 C16 C20 122.03(13) . . ? C12 C17 C19 110.19(12) . . ? C12 C17 C18 112.17(15) . . ? C19 C17 C18 110.89(14) . . ? C21 C20 C16 112.74(17) . . ? C21 C20 C22 111.29(18) . . ? C16 C20 C22 110.50(13) . . ? C36 C31 C32 123.31(11) . . ? C36 C31 N2 118.13(11) . . ? C32 C31 N2 118.48(11) . . ? C33 C32 C31 116.83(12) . . ? C33 C32 C37 121.11(12) . . ? C31 C32 C37 122.04(11) . . ? C34 C33 C32 121.26(13) . . ? C35 C34 C33 120.34(12) . . ? C34 C35 C36 121.21(13) . . ? C35 C36 C31 117.05(12) . . ? C35 C36 C40 120.01(12) . . ? C31 C36 C40 122.94(12) . . ? C38 C37 C32 112.68(12) . . ? C38 C37 C39 110.59(14) . . ? C32 C37 C39 110.26(12) . . ? C36 C40 C41 110.99(14) . . ? C36 C40 C42 111.39(13) . . ? C41 C40 C42 110.81(14) . . ? N3 B1 C1 113.52(10) . . ? C6S C1S C2S 115.9(2) . . ? C6S C1S C7S 120.5(3) . . ? C2S C1S C7S 123.5(3) . . ? C1S C2S C3S 118.4(3) . . ? C4S C3S C2S 119.4(3) . . ? C5S C4S C3S 121.7(3) . . ? C4S C5S C6S 121.4(4) . . ? C5S C6S C1S 123.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 0.17(13) . . . . ? C31 N2 C1 N1 174.45(10) . . . . ? C3 N2 C1 B1 -172.68(11) . . . . ? C31 N2 C1 B1 1.60(19) . . . . ? C2 N1 C1 N2 0.11(13) . . . . ? C11 N1 C1 N2 -174.50(10) . . . . ? C2 N1 C1 B1 172.85(12) . . . . ? C11 N1 C1 B1 -1.77(18) . . . . ? C1 N1 C2 C3 -0.36(14) . . . . ? C11 N1 C2 C3 174.36(11) . . . . ? N1 C2 C3 N2 0.45(14) . . . . ? C1 N2 C3 C2 -0.40(15) . . . . ? C31 N2 C3 C2 -174.96(11) . . . . ? C1 N1 C11 C12 -104.77(14) . . . . ? C2 N1 C11 C12 81.27(15) . . . . ? C1 N1 C11 C16 78.14(15) . . . . ? C2 N1 C11 C16 -95.82(15) . . . . ? C16 C11 C12 C13 -1.21(19) . . . . ? N1 C11 C12 C13 -178.13(11) . . . . ? C16 C11 C12 C17 176.00(12) . . . . ? N1 C11 C12 C17 -0.92(18) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C17 C12 C13 C14 -177.01(13) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C11 -0.9(2) . . . . ? C14 C15 C16 C20 175.92(15) . . . . ? C12 C11 C16 C15 1.5(2) . . . . ? N1 C11 C16 C15 178.48(12) . . . . ? C12 C11 C16 C20 -175.28(13) . . . . ? N1 C11 C16 C20 1.67(19) . . . . ? C13 C12 C17 C19 77.46(18) . . . . ? C11 C12 C17 C19 -99.65(16) . . . . ? C13 C12 C17 C18 -46.61(18) . . . . ? C11 C12 C17 C18 136.28(14) . . . . ? C15 C16 C20 C21 42.6(2) . . . . ? C11 C16 C20 C21 -140.73(16) . . . . ? C15 C16 C20 C22 -82.7(2) . . . . ? C11 C16 C20 C22 94.03(18) . . . . ? C1 N2 C31 C36 -84.89(15) . . . . ? C3 N2 C31 C36 88.78(15) . . . . ? C1 N2 C31 C32 98.34(14) . . . . ? C3 N2 C31 C32 -87.99(15) . . . . ? C36 C31 C32 C33 0.58(19) . . . . ? N2 C31 C32 C33 177.17(11) . . . . ? C36 C31 C32 C37 -177.81(12) . . . . ? N2 C31 C32 C37 -1.22(18) . . . . ? C31 C32 C33 C34 -0.2(2) . . . . ? C37 C32 C33 C34 178.25(13) . . . . ? C32 C33 C34 C35 -0.3(2) . . . . ? C33 C34 C35 C36 0.4(2) . . . . ? C34 C35 C36 C31 0.0(2) . . . . ? C34 C35 C36 C40 -179.75(14) . . . . ? C32 C31 C36 C35 -0.51(19) . . . . ? N2 C31 C36 C35 -177.12(11) . . . . ? C32 C31 C36 C40 179.25(13) . . . . ? N2 C31 C36 C40 2.65(19) . . . . ? C33 C32 C37 C38 46.10(18) . . . . ? C31 C32 C37 C38 -135.57(14) . . . . ? C33 C32 C37 C39 -77.99(17) . . . . ? C31 C32 C37 C39 100.34(16) . . . . ? C35 C36 C40 C41 -63.40(18) . . . . ? C31 C36 C40 C41 116.84(16) . . . . ? C35 C36 C40 C42 60.59(18) . . . . ? C31 C36 C40 C42 -119.17(15) . . . . ? C4 N3 B1 C1 -173.39(12) . . . . ? B2 N3 B1 C1 62.49(16) . . . . ? N2 C1 B1 N3 -129.11(12) . . . . ? N1 C1 B1 N3 59.69(16) . . . . ? C6S C1S C2S C3S 1.4(3) . . . . ? C7S C1S C2S C3S -178.3(2) . . . . ? C1S C2S C3S C4S 0.9(4) . . . . ? C2S C3S C4S C5S -3.8(5) . . . . ? C3S C4S C5S C6S 4.3(6) . . . . ? C4S C5S C6S C1S -1.8(5) . . . . ? C2S C1S C6S C5S -1.1(3) . . . . ? C7S C1S C6S C5S 178.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 70.74 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.368 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.059 data_riv12b9 _database_code_depnum_ccdc_archive 'CCDC 902242' #TrackingRef '16670_web_deposit_cif_file_1_EricRivard_1357602407.CCDC902242_Dalton_Rivard_Jan2013.cif' _vrf_CHEMW03_riv12b9 ; RESPONSE: Attempts to refine peaks of residual electron density as disordered or partial-occupancy solvent tetrahydrofuran oxygen or carbon atoms were unsuccessful. The data were corrected for disordered electron density through use of the SQUEEZE procedure (Sluis, P. van der; Spek, A. L. Acta Crystallogr. 1990, A46, 194-201) as implemented in PLATON (Spek, A. L. Acta Crystallogr. 1990, A46, C34; Spek, A. L. J. Appl. Cryst. 2003, 36, 7-13. PLATON - a multipurpose crystallographic tool. Utrecht University, Utrecht, The Netherlands). A total solvent-accessible void volume of 1174.0 cubic Angstroms with a total electron count of 244 (consistent with 6 molecules of solvent tetrahydrofuran, or 1.5 molecules per formula unit of the molecule of interest) was found in the unit cell. ; _vrf_PLAT051_riv12b9 ; RESPONSE: See above response to CHEMW03 alert (related to use of PLATON/SQUEEZE). ; _vrf_PLAT041_riv12b9 ; RESPONSE: See above response to CHEMW03 alert (related to use of PLATON/SQUEEZE). ; _vrf_PLAT068_riv12b9 ; RESPONSE: See above response to CHEMW03 alert (related to use of PLATON/SQUEEZE). ; _vrf_FORMU01_riv12b9 ; RESPONSE: See above response to CHEMW03 alert (related to use of PLATON/SQUEEZE). ; _vrf_CELLZ01_riv12b9 ; RESPONSE: See above response to CHEMW03 alert (related to use of PLATON/SQUEEZE). ; _vrf_PLAT606_riv12b9 ; RESPONSE: See above response to CHEMW03 alert (related to use of PLATON/SQUEEZE). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3 _chemical_melting_point ? _chemical_formula_moiety 'C31 H51 B2 N3, 1.5(C4 H8 O)' _chemical_formula_sum 'C37 H63 B2 N3 O1.5' _chemical_formula_weight 595.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.8935(5) _cell_length_b 13.6955(4) _cell_length_c 17.7459(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.4379(18) _cell_angle_gamma 90.00 _cell_volume 3917.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9806 _cell_measurement_theta_min 4.15 _cell_measurement_theta_max 68.90 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.010 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7885 _exptl_absorpt_correction_T_max 0.9554 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26141 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_unetl/netl 0.0382 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 69.88 _reflns_number_total 7069 _reflns_number_gt 6132 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.4605P] 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 7069 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 N1 N 0.20079(5) -0.04760(6) 0.29548(5) 0.0296(2) Uani 1 1 d . . . N2 N 0.08705(5) -0.01413(6) 0.20539(5) 0.0280(2) Uani 1 1 d . . . N3 N 0.15328(6) 0.13298(7) 0.39556(5) 0.0348(2) Uani 1 1 d . . . H3N H 0.2080(9) 0.1030(10) 0.4113(8) 0.045(4) Uiso 1 1 d . . . C1 C 0.12732(6) -0.00009(7) 0.28290(6) 0.0287(2) Uani 1 1 d . . . C2 C 0.20636(7) -0.09006(8) 0.22651(6) 0.0330(2) Uani 1 1 d . . . H2 H 0.2516 -0.1269 0.2202 0.040 Uiso 1 1 calc R . . C3 C 0.13529(7) -0.06905(7) 0.17024(6) 0.0323(2) Uani 1 1 d . . . H3 H 0.1208 -0.0882 0.1164 0.039 Uiso 1 1 calc R . . C4 C 0.13986(8) 0.15662(9) 0.47497(7) 0.0422(3) Uani 1 1 d . . . C5 C 0.16474(11) 0.06859(12) 0.52935(8) 0.0596(4) Uani 1 1 d . . . H5A H 0.2234 0.0536 0.5374 0.071 Uiso 1 1 calc R . . H5B H 0.1308 0.0122 0.5053 0.071 Uiso 1 1 calc R . . H5C H 0.1560 0.0833 0.5803 0.071 Uiso 1 1 calc R . . C6 C 0.19453(11) 0.24232(12) 0.51302(9) 0.0636(4) Uani 1 1 d . . . H6A H 0.1789 0.3000 0.4791 0.076 Uiso 1 1 calc R . . H6B H 0.2528 0.2261 0.5198 0.076 Uiso 1 1 calc R . . H6C H 0.1872 0.2561 0.5647 0.076 Uiso 1 1 calc R . . C7 C 0.04957(9) 0.18267(13) 0.46269(9) 0.0596(4) Uani 1 1 d . . . H7A H 0.0350 0.2403 0.4286 0.071 Uiso 1 1 calc R . . H7B H 0.0411 0.1968 0.5139 0.071 Uiso 1 1 calc R . . H7C H 0.0143 0.1277 0.4377 0.071 Uiso 1 1 calc R . . C11 C 0.25939(7) -0.06132(7) 0.37332(6) 0.0316(2) Uani 1 1 d . . . C12 C 0.32867(7) 0.00014(7) 0.39749(7) 0.0353(3) Uani 1 1 d . . . C13 C 0.37985(7) -0.01058(8) 0.47523(7) 0.0416(3) Uani 1 1 d . . . H13 H 0.4267 0.0308 0.4943 0.050 Uiso 1 1 calc R . . C14 C 0.36344(8) -0.08011(9) 0.52462(7) 0.0449(3) Uani 1 1 d . . . H14 H 0.3983 -0.0851 0.5776 0.054 Uiso 1 1 calc R . . C15 C 0.29689(8) -0.14256(9) 0.49782(7) 0.0431(3) Uani 1 1 d . . . H15 H 0.2874 -0.1913 0.5322 0.052 Uiso 1 1 calc R . . C16 C 0.24339(7) -0.13526(8) 0.42119(7) 0.0364(3) Uani 1 1 d . . . C17 C 0.35065(7) 0.07132(8) 0.34160(8) 0.0423(3) Uani 1 1 d . . . H17 H 0.2988 0.0870 0.2983 0.051 Uiso 1 1 calc R . . C18 C 0.38694(9) 0.16699(10) 0.38169(10) 0.0592(4) Uani 1 1 d . . . H18A H 0.3470 0.1980 0.4044 0.071 Uiso 1 1 calc R . . H18B H 0.3986 0.2108 0.3427 0.071 Uiso 1 1 calc R . . H18C H 0.4385 0.1535 0.4237 0.071 Uiso 1 1 calc R . . C19 C 0.41156(9) 0.02249(10) 0.30450(8) 0.0501(3) Uani 1 1 d . . . H19A H 0.3877 -0.0388 0.2792 0.060 Uiso 1 1 calc R . . H19B H 0.4638 0.0088 0.3457 0.060 Uiso 1 1 calc R . . H19C H 0.4222 0.0662 0.2649 0.060 Uiso 1 1 calc R . . C20 C 0.17383(8) -0.20904(9) 0.39105(8) 0.0460(3) Uani 1 1 d . . . H20 H 0.1334 -0.1808 0.3428 0.055 Uiso 1 1 calc R . . C21 C 0.12696(12) -0.23132(13) 0.44958(12) 0.0726(5) Uani 1 1 d . . . H21A H 0.0820 -0.2773 0.4259 0.087 Uiso 1 1 calc R . . H21B H 0.1037 -0.1708 0.4634 0.087 Uiso 1 1 calc R . . H21C H 0.1649 -0.2603 0.4973 0.087 Uiso 1 1 calc R . . C22 C 0.20824(11) -0.30283(12) 0.36653(11) 0.0668(4) Uani 1 1 d . . . H22A H 0.2356 -0.2878 0.3264 0.080 Uiso 1 1 calc R . . H22B H 0.1627 -0.3489 0.3448 0.080 Uiso 1 1 calc R . . H22C H 0.2485 -0.3320 0.4127 0.080 Uiso 1 1 calc R . . C31 C 0.00122(6) 0.01062(7) 0.16478(6) 0.0307(2) Uani 1 1 d . . . C32 C -0.01552(7) 0.09161(8) 0.11476(6) 0.0348(3) Uani 1 1 d . . . C33 C -0.09859(8) 0.10888(9) 0.07261(7) 0.0447(3) Uani 1 1 d . . . H33 H -0.1123 0.1635 0.0381 0.054 Uiso 1 1 calc R . . C34 C -0.16078(8) 0.04831(10) 0.08009(8) 0.0495(3) Uani 1 1 d . . . H34 H -0.2167 0.0610 0.0503 0.059 Uiso 1 1 calc R . . C35 C -0.14254(8) -0.03073(10) 0.13061(7) 0.0439(3) Uani 1 1 d . . . H35 H -0.1862 -0.0714 0.1357 0.053 Uiso 1 1 calc R . . C36 C -0.06074(7) -0.05181(8) 0.17443(6) 0.0347(2) Uani 1 1 d . . . C37 C 0.05185(8) 0.15794(8) 0.10341(6) 0.0384(3) Uani 1 1 d . . . H37 H 0.1058 0.1373 0.1416 0.046 Uiso 1 1 calc R . . C38 C 0.03727(10) 0.26494(9) 0.11989(8) 0.0527(3) Uani 1 1 d . . . H38A H 0.0831 0.3047 0.1136 0.063 Uiso 1 1 calc R . . H38B H 0.0344 0.2715 0.1740 0.063 Uiso 1 1 calc R . . H38C H -0.0150 0.2872 0.0826 0.063 Uiso 1 1 calc R . . C39 C 0.05879(9) 0.14604(10) 0.02017(7) 0.0481(3) Uani 1 1 d . . . H39A H 0.1031 0.1883 0.0137 0.058 Uiso 1 1 calc R . . H39B H 0.0061 0.1643 -0.0185 0.058 Uiso 1 1 calc R . . H39C H 0.0716 0.0779 0.0118 0.058 Uiso 1 1 calc R . . C40 C -0.04315(7) -0.13972(9) 0.22898(7) 0.0397(3) Uani 1 1 d . . . H40 H 0.0183 -0.1440 0.2538 0.048 Uiso 1 1 calc R . . C41 C -0.08299(10) -0.12861(12) 0.29505(8) 0.0576(4) Uani 1 1 d . . . H41A H -0.0692 -0.1854 0.3301 0.069 Uiso 1 1 calc R . . H41B H -0.1434 -0.1241 0.2722 0.069 Uiso 1 1 calc R . . H41C H -0.0621 -0.0692 0.3253 0.069 Uiso 1 1 calc R . . C42 C -0.07182(10) -0.23449(9) 0.18362(8) 0.0501(3) Uani 1 1 d . . . H42A H -0.0585 -0.2898 0.2203 0.060 Uiso 1 1 calc R . . H42B H -0.0435 -0.2425 0.1432 0.060 Uiso 1 1 calc R . . H42C H -0.1319 -0.2319 0.1582 0.060 Uiso 1 1 calc R . . B1 B 0.09074(8) 0.05261(9) 0.34636(7) 0.0350(3) Uani 1 1 d . . . H1BA H 0.0305(9) 0.0865(10) 0.3138(8) 0.045(4) Uiso 1 1 d . . . H1BB H 0.0806(8) -0.0071(10) 0.3860(8) 0.041(3) Uiso 1 1 d . . . B2 B 0.15810(11) 0.22440(10) 0.33951(9) 0.0471(3) Uani 1 1 d . . . H2BA H 0.2160(10) 0.2698(11) 0.3712(10) 0.059(4) Uiso 1 1 d . . . H2BB H 0.1672(9) 0.1906(10) 0.2838(8) 0.045(4) Uiso 1 1 d . . . H2BC H 0.0999(10) 0.2674(11) 0.3278(9) 0.059(4) 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 N1 0.0302(4) 0.0290(4) 0.0267(4) -0.0019(3) 0.0043(4) 0.0004(3) N2 0.0302(4) 0.0277(4) 0.0238(4) -0.0017(3) 0.0045(4) -0.0011(3) N3 0.0357(5) 0.0390(5) 0.0289(4) -0.0072(4) 0.0084(4) 0.0003(4) C1 0.0305(5) 0.0265(5) 0.0266(5) -0.0005(4) 0.0044(4) -0.0023(4) C2 0.0347(5) 0.0320(5) 0.0321(5) -0.0052(4) 0.0098(5) 0.0004(4) C3 0.0370(6) 0.0322(5) 0.0271(5) -0.0053(4) 0.0086(4) -0.0015(4) C4 0.0441(6) 0.0516(7) 0.0312(5) -0.0126(5) 0.0116(5) 0.0000(5) C5 0.0784(10) 0.0689(9) 0.0329(6) -0.0026(6) 0.0191(7) 0.0066(8) C6 0.0712(10) 0.0726(10) 0.0473(8) -0.0286(7) 0.0184(7) -0.0166(8) C7 0.0510(8) 0.0817(10) 0.0493(7) -0.0179(7) 0.0201(7) 0.0091(7) C11 0.0307(5) 0.0321(5) 0.0280(5) -0.0013(4) 0.0026(4) 0.0040(4) C12 0.0329(5) 0.0306(5) 0.0372(6) -0.0021(4) 0.0026(5) 0.0032(4) C13 0.0356(6) 0.0396(6) 0.0403(6) -0.0058(5) -0.0026(5) 0.0022(5) C14 0.0442(7) 0.0518(7) 0.0310(6) -0.0002(5) -0.0005(5) 0.0095(5) C15 0.0424(6) 0.0489(7) 0.0354(6) 0.0085(5) 0.0074(5) 0.0076(5) C16 0.0340(6) 0.0385(6) 0.0349(6) 0.0029(4) 0.0075(5) 0.0038(4) C17 0.0351(6) 0.0356(6) 0.0478(7) 0.0076(5) 0.0000(5) -0.0022(4) C18 0.0525(8) 0.0372(6) 0.0816(10) 0.0021(6) 0.0104(7) -0.0070(6) C19 0.0475(7) 0.0503(7) 0.0508(7) 0.0085(6) 0.0124(6) -0.0055(6) C20 0.0388(6) 0.0470(7) 0.0466(7) 0.0129(5) 0.0044(5) -0.0049(5) C21 0.0722(10) 0.0635(9) 0.0963(13) 0.0005(9) 0.0466(10) -0.0163(8) C22 0.0661(10) 0.0624(9) 0.0721(10) -0.0230(8) 0.0209(8) -0.0223(7) C31 0.0309(5) 0.0323(5) 0.0248(5) -0.0048(4) 0.0023(4) -0.0002(4) C32 0.0389(6) 0.0324(5) 0.0288(5) -0.0027(4) 0.0038(5) 0.0013(4) C33 0.0439(7) 0.0403(6) 0.0421(6) 0.0043(5) 0.0009(5) 0.0084(5) C34 0.0346(6) 0.0556(7) 0.0502(7) 0.0020(6) 0.0003(6) 0.0078(5) C35 0.0322(6) 0.0526(7) 0.0436(6) -0.0017(5) 0.0066(5) -0.0027(5) C36 0.0328(6) 0.0401(6) 0.0295(5) -0.0034(4) 0.0066(5) -0.0018(4) C37 0.0464(6) 0.0325(5) 0.0299(5) 0.0022(4) 0.0017(5) -0.0036(5) C38 0.0735(9) 0.0346(6) 0.0449(7) -0.0006(5) 0.0098(7) -0.0044(6) C39 0.0575(8) 0.0470(7) 0.0377(6) -0.0014(5) 0.0109(6) -0.0103(6) C40 0.0364(6) 0.0471(6) 0.0325(5) 0.0037(5) 0.0058(5) -0.0073(5) C41 0.0717(10) 0.0651(9) 0.0398(7) -0.0046(6) 0.0227(7) -0.0200(7) C42 0.0619(8) 0.0432(7) 0.0451(7) 0.0017(5) 0.0158(6) -0.0022(6) B1 0.0329(6) 0.0403(6) 0.0298(6) -0.0066(5) 0.0063(5) 0.0001(5) B2 0.0602(9) 0.0383(7) 0.0436(7) -0.0016(6) 0.0170(7) 0.0004(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 N1 C1 1.3592(13) . ? N1 C2 1.3835(13) . ? N1 C11 1.4505(13) . ? N2 C1 1.3530(13) . ? N2 C3 1.3871(14) . ? N2 C31 1.4527(13) . ? N3 C4 1.5276(14) . ? N3 B1 1.5929(15) . ? N3 B2 1.6162(17) . ? N3 H3N 0.972(15) . ? C1 B1 1.6088(16) . ? C2 C3 1.3428(15) . ? C4 C7 1.5172(19) . ? C4 C6 1.5208(18) . ? C4 C5 1.5226(19) . ? C11 C16 1.3991(16) . ? C11 C12 1.4005(15) . ? C12 C13 1.3991(16) . ? C12 C17 1.5142(17) . ? C13 C14 1.3774(19) . ? C14 C15 1.3789(19) . ? C15 C16 1.3927(16) . ? C16 C20 1.5204(17) . ? C17 C18 1.5289(17) . ? C17 C19 1.531(2) . ? C20 C21 1.514(2) . ? C20 C22 1.526(2) . ? C31 C32 1.3956(15) . ? C31 C36 1.4011(16) . ? C32 C33 1.3984(16) . ? C32 C37 1.5160(16) . ? C33 C34 1.376(2) . ? C34 C35 1.3802(19) . ? C35 C36 1.3977(16) . ? C36 C40 1.5175(16) . ? C37 C39 1.5251(17) . ? C37 C38 1.5287(17) . ? C40 C41 1.5244(19) . ? C40 C42 1.5275(17) . ? B1 H1BA 1.111(14) . ? B1 H1BB 1.125(13) . ? B2 H2BA 1.153(16) . ? B2 H2BB 1.142(14) . ? B2 H2BC 1.110(16) . ? 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 C2 110.90(8) . . ? C1 N1 C11 123.20(9) . . ? C2 N1 C11 125.45(9) . . ? C1 N2 C3 110.49(8) . . ? C1 N2 C31 126.46(9) . . ? C3 N2 C31 122.48(8) . . ? C4 N3 B1 113.25(9) . . ? C4 N3 B2 116.90(9) . . ? B1 N3 B2 110.21(9) . . ? C4 N3 H3N 102.4(8) . . ? B1 N3 H3N 106.4(8) . . ? B2 N3 H3N 106.5(8) . . ? N2 C1 N1 104.79(9) . . ? N2 C1 B1 126.42(9) . . ? N1 C1 B1 128.54(9) . . ? C3 C2 N1 106.56(9) . . ? C2 C3 N2 107.26(9) . . ? C7 C4 C6 109.44(12) . . ? C7 C4 C5 110.61(13) . . ? C6 C4 C5 108.31(12) . . ? C7 C4 N3 109.76(10) . . ? C6 C4 N3 109.56(11) . . ? C5 C4 N3 109.13(10) . . ? C16 C11 C12 123.01(10) . . ? C16 C11 N1 118.11(9) . . ? C12 C11 N1 118.88(9) . . ? C13 C12 C11 116.86(11) . . ? C13 C12 C17 120.86(10) . . ? C11 C12 C17 122.20(10) . . ? C14 C13 C12 121.14(11) . . ? C13 C14 C15 120.54(11) . . ? C14 C15 C16 121.05(11) . . ? C15 C16 C11 117.25(11) . . ? C15 C16 C20 120.19(11) . . ? C11 C16 C20 122.48(10) . . ? C12 C17 C18 112.94(11) . . ? C12 C17 C19 109.19(9) . . ? C18 C17 C19 110.30(11) . . ? C21 C20 C16 113.62(12) . . ? C21 C20 C22 110.38(12) . . ? C16 C20 C22 109.84(11) . . ? C32 C31 C36 123.12(10) . . ? C32 C31 N2 118.87(10) . . ? C36 C31 N2 117.91(9) . . ? C31 C32 C33 117.01(11) . . ? C31 C32 C37 122.94(10) . . ? C33 C32 C37 120.03(10) . . ? C34 C33 C32 121.29(11) . . ? C33 C34 C35 120.48(11) . . ? C34 C35 C36 120.95(12) . . ? C35 C36 C31 117.15(10) . . ? C35 C36 C40 119.39(11) . . ? C31 C36 C40 123.46(10) . . ? C32 C37 C39 110.08(9) . . ? C32 C37 C38 112.25(11) . . ? C39 C37 C38 110.57(10) . . ? C36 C40 C41 111.36(11) . . ? C36 C40 C42 111.56(9) . . ? C41 C40 C42 110.28(10) . . ? N3 B1 C1 111.28(9) . . ? N3 B1 H1BA 110.5(7) . . ? N3 B1 H1BB 111.1(7) . . ? C1 B1 H1BA 108.0(7) . . ? C1 B1 H1BB 105.9(7) . . ? H1BA B1 H1BB 110.0(10) . . ? N3 B2 H2BA 108.0(8) . . ? N3 B2 H2BB 105.3(7) . . ? N3 B2 H2BC 108.7(8) . . ? H2BA B2 H2BB 108.9(11) . . ? H2BA B2 H2BC 112.3(11) . . ? H2BB B2 H2BC 113.2(11) . . ? 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 C3 N2 C1 N1 -0.47(11) . . . . ? C31 N2 C1 N1 170.97(9) . . . . ? C3 N2 C1 B1 -175.13(10) . . . . ? C31 N2 C1 B1 -3.68(16) . . . . ? C2 N1 C1 N2 0.43(11) . . . . ? C11 N1 C1 N2 -172.25(9) . . . . ? C2 N1 C1 B1 174.93(10) . . . . ? C11 N1 C1 B1 2.25(16) . . . . ? C1 N1 C2 C3 -0.22(12) . . . . ? C11 N1 C2 C3 172.25(10) . . . . ? N1 C2 C3 N2 -0.08(12) . . . . ? C1 N2 C3 C2 0.35(12) . . . . ? C31 N2 C3 C2 -171.49(9) . . . . ? B1 N3 C4 C7 -52.81(14) . . . . ? B2 N3 C4 C7 76.94(14) . . . . ? B1 N3 C4 C6 -173.01(11) . . . . ? B2 N3 C4 C6 -43.26(15) . . . . ? B1 N3 C4 C5 68.55(13) . . . . ? B2 N3 C4 C5 -161.69(12) . . . . ? C1 N1 C11 C16 78.70(13) . . . . ? C2 N1 C11 C16 -92.90(13) . . . . ? C1 N1 C11 C12 -100.72(12) . . . . ? C2 N1 C11 C12 87.69(13) . . . . ? C16 C11 C12 C13 -4.39(17) . . . . ? N1 C11 C12 C13 174.99(9) . . . . ? C16 C11 C12 C17 172.33(11) . . . . ? N1 C11 C12 C17 -8.28(16) . . . . ? C11 C12 C13 C14 1.51(17) . . . . ? C17 C12 C13 C14 -175.26(11) . . . . ? C12 C13 C14 C15 1.50(19) . . . . ? C13 C14 C15 C16 -1.8(2) . . . . ? C14 C15 C16 C11 -0.90(18) . . . . ? C14 C15 C16 C20 175.92(12) . . . . ? C12 C11 C16 C15 4.11(17) . . . . ? N1 C11 C16 C15 -175.28(10) . . . . ? C12 C11 C16 C20 -172.63(11) . . . . ? N1 C11 C16 C20 7.98(16) . . . . ? C13 C12 C17 C18 -39.26(15) . . . . ? C11 C12 C17 C18 144.15(12) . . . . ? C13 C12 C17 C19 83.85(13) . . . . ? C11 C12 C17 C19 -92.74(13) . . . . ? C15 C16 C20 C21 44.37(17) . . . . ? C11 C16 C20 C21 -138.98(13) . . . . ? C15 C16 C20 C22 -79.81(15) . . . . ? C11 C16 C20 C22 96.84(14) . . . . ? C1 N2 C31 C32 105.73(12) . . . . ? C3 N2 C31 C32 -83.78(12) . . . . ? C1 N2 C31 C36 -77.89(13) . . . . ? C3 N2 C31 C36 92.60(12) . . . . ? C36 C31 C32 C33 -0.52(16) . . . . ? N2 C31 C32 C33 175.66(10) . . . . ? C36 C31 C32 C37 -178.90(10) . . . . ? N2 C31 C32 C37 -2.71(15) . . . . ? C31 C32 C33 C34 -0.25(18) . . . . ? C37 C32 C33 C34 178.18(12) . . . . ? C32 C33 C34 C35 0.9(2) . . . . ? C33 C34 C35 C36 -0.8(2) . . . . ? C34 C35 C36 C31 0.09(18) . . . . ? C34 C35 C36 C40 -179.64(12) . . . . ? C32 C31 C36 C35 0.59(16) . . . . ? N2 C31 C36 C35 -175.62(10) . . . . ? C32 C31 C36 C40 -179.69(10) . . . . ? N2 C31 C36 C40 4.10(15) . . . . ? C31 C32 C37 C39 111.17(12) . . . . ? C33 C32 C37 C39 -67.16(14) . . . . ? C31 C32 C37 C38 -125.21(11) . . . . ? C33 C32 C37 C38 56.46(14) . . . . ? C35 C36 C40 C41 -63.48(14) . . . . ? C31 C36 C40 C41 116.81(12) . . . . ? C35 C36 C40 C42 60.21(15) . . . . ? C31 C36 C40 C42 -119.50(12) . . . . ? C4 N3 B1 C1 -157.67(9) . . . . ? B2 N3 B1 C1 69.27(12) . . . . ? N2 C1 B1 N3 -130.68(10) . . . . ? N1 C1 B1 N3 55.93(14) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.205 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.033 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 _platon_squeeze_void_content 1 0.307 -0.151 0.807 1174 244 ' ' _platon_squeeze_details ; Attempts to refine peaks of residual electron density as disordered or partial-occupancy solvent tetrahydrofuran oxygen or carbon atoms were unsuccessful. The data were corrected for disordered electron density through use of the SQUEEZE procedure (Sluis, P. van der; Spek, A. L. Acta Crystallogr. 1990, A46, 194-201) as implemented in PLATON (Spek, A. L. Acta Crystallogr. 1990, A46, C34; Spek, A. L. J. Appl. Cryst. 2003, 36, 7-13. PLATON - a multipurpose crystallographic tool. Utrecht University, Utrecht, The Netherlands). A total solvent-accessible void volume of 1174.0 cubic Angstroms with a total electron count of 244 (consistent with 6 molecules of solvent tetrahydrofuran, or 1.5 molecules per formula unit of the molecule of interest) was found in the unit cell. ; data_riv12c3 _database_code_depnum_ccdc_archive 'CCDC 902243' #TrackingRef '16671_web_deposit_cif_file_2_EricRivard_1357602407.CCDC902243_Dalton_Rivard_Jan2013.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6 _chemical_melting_point ? _chemical_formula_moiety 'C12 H22 B N' _chemical_formula_sum 'C12 H22 B N' _chemical_formula_weight 191.12 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.4951(12) _cell_length_b 15.4951(12) _cell_length_c 27.816(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5783.9(8) _cell_formula_units_Z 18 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5867 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 25.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1908 _exptl_absorpt_coefficient_mu 0.055 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9735 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13920 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_unetl/netl 0.0167 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2343 _reflns_number_gt 1921 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+3.2448P] 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 2343 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 N N 0.78096(7) 0.88569(7) 0.05270(4) 0.0295(3) Uani 1 1 d . . . H1NA H 0.7790(10) 0.8979(10) 0.0208(6) 0.041(4) Uiso 1 1 d . . . H1NB H 0.8237(11) 0.9486(11) 0.0658(5) 0.045(4) Uiso 1 1 d . . . C1 C 0.68173(8) 0.84862(8) 0.07336(4) 0.0279(3) Uani 1 1 d . . . C2 C 0.67489(9) 0.87709(9) 0.12022(4) 0.0321(3) Uani 1 1 d . . . C3 C 0.58013(10) 0.84713(10) 0.13811(5) 0.0413(3) Uani 1 1 d . . . H3 H 0.5733 0.8672 0.1695 0.050 Uiso 1 1 calc R . . C4 C 0.49660(10) 0.78918(11) 0.11128(5) 0.0473(4) Uani 1 1 d . . . H4 H 0.4326 0.7708 0.1238 0.057 Uiso 1 1 calc R . . C5 C 0.50536(10) 0.75765(10) 0.06626(5) 0.0427(3) Uani 1 1 d . . . H5 H 0.4467 0.7153 0.0486 0.051 Uiso 1 1 calc R . . C6 C 0.59773(9) 0.78613(8) 0.04596(4) 0.0323(3) Uani 1 1 d . . . C7 C 0.76508(10) 0.93928(10) 0.15177(4) 0.0381(3) Uani 1 1 d . . . H7 H 0.8253 0.9488 0.1339 0.046 Uiso 1 1 calc R . . C8 C 0.75960(15) 0.88640(12) 0.19859(6) 0.0679(5) Uani 1 1 d . . . H8A H 0.8180 0.9291 0.2183 0.082 Uiso 1 1 calc R . . H8B H 0.7583 0.8238 0.1916 0.082 Uiso 1 1 calc R . . H8C H 0.6989 0.8722 0.2160 0.082 Uiso 1 1 calc R . . C9 C 0.77852(12) 1.04145(10) 0.16125(6) 0.0541(4) Uani 1 1 d . . . H9A H 0.7877 1.0764 0.1307 0.065 Uiso 1 1 calc R . . H9B H 0.8373 1.0797 0.1816 0.065 Uiso 1 1 calc R . . H9C H 0.7193 1.0344 0.1776 0.065 Uiso 1 1 calc R . . C10 C 0.60153(10) 0.74528(9) -0.00321(4) 0.0377(3) Uani 1 1 d . . . H10 H 0.6726 0.7799 -0.0140 0.045 Uiso 1 1 calc R . . C11 C 0.56536(12) 0.63395(10) 0.00015(6) 0.0535(4) Uani 1 1 d . . . H11A H 0.6044 0.6227 0.0245 0.064 Uiso 1 1 calc R . . H11B H 0.5736 0.6098 -0.0311 0.064 Uiso 1 1 calc R . . H11C H 0.4948 0.5980 0.0092 0.064 Uiso 1 1 calc R . . C12 C 0.54102(12) 0.76449(11) -0.04077(5) 0.0523(4) Uani 1 1 d . . . H12A H 0.5633 0.8358 -0.0417 0.063 Uiso 1 1 calc R . . H12B H 0.4702 0.7271 -0.0322 0.063 Uiso 1 1 calc R . . H12C H 0.5507 0.7429 -0.0724 0.063 Uiso 1 1 calc R . . B B 0.83132(12) 0.81704(12) 0.06095(6) 0.0399(4) Uani 1 1 d . . . H1BA H 0.9094(10) 0.8602(10) 0.0455(5) 0.047(4) Uiso 1 1 d . . . H1BB H 0.7842(11) 0.7466(10) 0.0404(5) 0.047(4) Uiso 1 1 d . . . H1BC H 0.8352(11) 0.8065(11) 0.0993(5) 0.053(4) 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 N 0.0286(5) 0.0281(5) 0.0298(6) -0.0002(4) 0.0005(4) 0.0126(4) C1 0.0294(6) 0.0241(6) 0.0314(6) 0.0028(4) 0.0015(5) 0.0143(5) C2 0.0386(7) 0.0291(6) 0.0326(6) 0.0004(5) 0.0005(5) 0.0199(5) C3 0.0463(8) 0.0437(8) 0.0380(7) 0.0017(6) 0.0089(6) 0.0257(6) C4 0.0346(7) 0.0504(8) 0.0538(9) 0.0053(7) 0.0116(6) 0.0190(7) C5 0.0298(7) 0.0402(7) 0.0489(8) 0.0007(6) -0.0010(6) 0.0106(6) C6 0.0325(6) 0.0268(6) 0.0343(7) 0.0031(5) -0.0007(5) 0.0125(5) C7 0.0453(8) 0.0394(7) 0.0333(7) -0.0072(5) -0.0046(5) 0.0238(6) C8 0.0964(14) 0.0500(9) 0.0538(10) -0.0032(7) -0.0300(9) 0.0338(9) C9 0.0635(10) 0.0378(8) 0.0578(9) -0.0071(7) -0.0115(7) 0.0230(7) C10 0.0394(7) 0.0312(7) 0.0346(7) -0.0032(5) -0.0046(5) 0.0117(6) C11 0.0645(10) 0.0363(8) 0.0551(9) -0.0078(6) -0.0088(7) 0.0216(7) C12 0.0584(9) 0.0467(8) 0.0421(8) -0.0022(6) -0.0145(7) 0.0189(7) B 0.0448(9) 0.0460(9) 0.0403(8) 0.0004(7) 0.0034(7) 0.0312(8) _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 N C1 1.4633(14) . ? N B 1.6197(17) . ? N H1NA 0.911(15) . ? N H1NB 0.936(15) . ? C1 C2 1.3970(16) . ? C1 C6 1.3971(16) . ? C2 C3 1.3920(18) . ? C2 C7 1.5183(17) . ? C3 C4 1.3697(19) . ? C4 C5 1.375(2) . ? C5 C6 1.3895(18) . ? C6 C10 1.5207(17) . ? C7 C9 1.5131(18) . ? C7 C8 1.518(2) . ? C10 C11 1.5269(18) . ? C10 C12 1.5293(19) . ? B H1BA 1.134(14) . ? B H1BB 1.120(14) . ? B H1BC 1.085(15) . ? 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 N B 116.31(10) . . ? C1 N H1NA 109.0(9) . . ? B N H1NA 110.6(9) . . ? C1 N H1NB 108.3(8) . . ? B N H1NB 107.8(9) . . ? H1NA N H1NB 104.1(12) . . ? C2 C1 C6 122.43(11) . . ? C2 C1 N 118.25(10) . . ? C6 C1 N 119.32(10) . . ? C3 C2 C1 117.53(11) . . ? C3 C2 C7 119.19(11) . . ? C1 C2 C7 123.28(11) . . ? C4 C3 C2 121.15(12) . . ? C3 C4 C5 120.02(12) . . ? C4 C5 C6 121.74(12) . . ? C5 C6 C1 116.95(11) . . ? C5 C6 C10 118.78(11) . . ? C1 C6 C10 124.24(11) . . ? C9 C7 C8 110.88(12) . . ? C9 C7 C2 111.49(11) . . ? C8 C7 C2 111.59(12) . . ? C6 C10 C11 110.27(11) . . ? C6 C10 C12 112.23(11) . . ? C11 C10 C12 110.33(11) . . ? N B H1BA 106.4(7) . . ? N B H1BB 106.0(7) . . ? H1BA B H1BB 111.4(10) . . ? N B H1BC 108.6(8) . . ? H1BA B H1BC 109.7(10) . . ? H1BB B H1BC 114.4(10) . . ? 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 N C1 C2 90.20(13) . . . . ? B N C1 C6 -89.48(14) . . . . ? C6 C1 C2 C3 -4.84(17) . . . . ? N C1 C2 C3 175.49(10) . . . . ? C6 C1 C2 C7 175.83(11) . . . . ? N C1 C2 C7 -3.83(17) . . . . ? C1 C2 C3 C4 2.06(19) . . . . ? C7 C2 C3 C4 -178.58(12) . . . . ? C2 C3 C4 C5 1.5(2) . . . . ? C3 C4 C5 C6 -2.5(2) . . . . ? C4 C5 C6 C1 -0.11(19) . . . . ? C4 C5 C6 C10 177.79(12) . . . . ? C2 C1 C6 C5 3.87(17) . . . . ? N C1 C6 C5 -176.46(11) . . . . ? C2 C1 C6 C10 -173.90(11) . . . . ? N C1 C6 C10 5.76(17) . . . . ? C3 C2 C7 C9 -66.67(15) . . . . ? C1 C2 C7 C9 112.65(14) . . . . ? C3 C2 C7 C8 57.92(16) . . . . ? C1 C2 C7 C8 -122.76(14) . . . . ? C5 C6 C10 C11 -69.46(16) . . . . ? C1 C6 C10 C11 108.27(14) . . . . ? C5 C6 C10 C12 53.97(16) . . . . ? C1 C6 C10 C12 -128.29(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.140 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.031 data_riv1208 _database_code_depnum_ccdc_archive 'CCDC 902244' #TrackingRef '16672_web_deposit_cif_file_3_EricRivard_1357602407.CCDC902244_Dalton_Rivard_Jan2013.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 7 _chemical_melting_point ? _chemical_formula_moiety 'C33 H32 B N, C2 H4 Cl2' _chemical_formula_sum 'C35 H36 B Cl2 N' _chemical_formula_weight 552.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 42/m b c' _symmetry_space_group_name_Hall '-P 4c 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z+1/2' 'y, -x, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z-1/2' '-y, x, -z-1/2' '-x-1/2, y-1/2, -z' 'x-1/2, -y-1/2, -z' 'y-1/2, x-1/2, -z-1/2' '-y-1/2, -x-1/2, -z-1/2' _cell_length_a 17.2578(2) _cell_length_b 17.2578(2) _cell_length_c 20.4652(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6095.18(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9632 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 70.05 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 2.082 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6053 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39954 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_unetl/netl 0.0087 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 70.73 _reflns_number_total 2898 _reflns_number_gt 2758 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+2.8937P] 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 2898 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 N N 0.20260(9) 0.32828(9) 0.5000 0.0272(4) Uani 1 2 d S . . H1N H 0.2306(11) 0.3129(11) 0.4635(10) 0.043(5) Uiso 1 1 d . . . C1 C 0.12841(10) 0.28704(11) 0.5000 0.0257(4) Uani 1 2 d S . . C2 C 0.09390(7) 0.26787(8) 0.55962(7) 0.0268(3) Uani 1 1 d . . . C3 C 0.01974(8) 0.23568(8) 0.55834(7) 0.0294(3) Uani 1 1 d . . . H3 H -0.0050 0.2231 0.5984 0.035 Uiso 1 1 calc R . . C4 C -0.01886(11) 0.22160(12) 0.5000 0.0304(4) Uani 1 2 d S . . C5 C 0.13672(8) 0.28062(8) 0.62413(7) 0.0281(3) Uani 1 1 d . . . H5 H 0.1468 0.3375 0.6278 0.034 Uiso 1 1 calc R . . C6 C -0.10104(12) 0.19160(14) 0.5000 0.0384(5) Uani 1 2 d S . . H6A H -0.1147 0.1737 0.5440 0.046 Uiso 0.50 1 calc PR . . H6B H -0.1054 0.1484 0.4692 0.046 Uiso 0.50 1 calc PR . . H6C H -0.1364 0.2332 0.4869 0.046 Uiso 0.50 1 calc PR . . C11 C 0.21589(8) 0.24017(8) 0.62602(7) 0.0282(3) Uani 1 1 d . . . C12 C 0.27386(9) 0.27194(10) 0.66479(8) 0.0350(4) Uani 1 1 d . . . H12 H 0.2643 0.3187 0.6879 0.042 Uiso 1 1 calc R . . C13 C 0.34567(9) 0.23598(10) 0.67012(9) 0.0430(4) Uani 1 1 d . . . H13 H 0.3848 0.2580 0.6969 0.052 Uiso 1 1 calc R . . C14 C 0.36001(9) 0.16809(10) 0.63634(9) 0.0427(4) Uani 1 1 d . . . H14 H 0.4091 0.1436 0.6398 0.051 Uiso 1 1 calc R . . C15 C 0.30295(9) 0.13596(9) 0.59767(8) 0.0390(4) Uani 1 1 d . . . H15 H 0.3129 0.0893 0.5745 0.047 Uiso 1 1 calc R . . C16 C 0.23089(8) 0.17167(8) 0.59246(8) 0.0324(3) Uani 1 1 d . . . H16 H 0.1918 0.1492 0.5659 0.039 Uiso 1 1 calc R . . C21 C 0.09038(8) 0.25723(9) 0.68455(7) 0.0311(3) Uani 1 1 d . . . C22 C 0.05356(8) 0.31344(10) 0.72199(8) 0.0372(4) Uani 1 1 d . . . H22 H 0.0551 0.3661 0.7084 0.045 Uiso 1 1 calc R . . C23 C 0.01457(10) 0.29366(12) 0.77887(9) 0.0473(4) Uani 1 1 d . . . H23 H -0.0098 0.3328 0.8042 0.057 Uiso 1 1 calc R . . C24 C 0.01105(10) 0.21726(12) 0.79877(9) 0.0490(5) Uani 1 1 d . . . H24 H -0.0151 0.2039 0.8380 0.059 Uiso 1 1 calc R . . C25 C 0.04566(10) 0.16054(11) 0.76135(9) 0.0454(4) Uani 1 1 d . . . H25 H 0.0423 0.1078 0.7743 0.054 Uiso 1 1 calc R . . C26 C 0.08541(9) 0.18036(9) 0.70477(8) 0.0385(4) Uani 1 1 d . . . H26 H 0.1095 0.1409 0.6795 0.046 Uiso 1 1 calc R . . B B 0.19834(15) 0.42325(15) 0.5000 0.0407(6) Uani 1 2 d S . . H1BA H 0.1661(12) 0.4390(12) 0.4536(10) 0.061(6) Uiso 1 1 d . . . H1BB H 0.2635(19) 0.447(2) 0.5000 0.071(10) Uiso 1 2 d S . . Cl1S Cl 0.0000 0.5000 0.60527(4) 0.0619(2) Uani 1 2 d S . . C1S C -0.0135(5) 0.4668(6) 0.5153(5) 0.0392(9) Uiso 0.25 1 d P A -1 H1SA H 0.0182 0.4201 0.5065 0.047 Uiso 0.25 1 calc PR A -1 H1SB H -0.0685 0.4540 0.5069 0.047 Uiso 0.25 1 calc PR A -1 C2S C 0.0120(6) 0.5326(6) 0.4723(6) 0.0392(9) Uiso 0.25 1 d P . -1 H2SA H 0.0669 0.5458 0.4806 0.047 Uiso 0.25 1 calc PR . -1 H2SB H -0.0202 0.5791 0.4802 0.047 Uiso 0.25 1 calc PR . -1 Cl2S Cl 0.0000 0.0000 0.60489(6) 0.1408(7) Uani 1 2 d S . . C3S C -0.0439(5) -0.0187(5) 0.5185(4) 0.0593(16) Uiso 0.25 1 d P B -1 H3SA H -0.0530 -0.0747 0.5109 0.071 Uiso 0.25 1 calc PR B -1 H3SB H -0.0931 0.0099 0.5123 0.071 Uiso 0.25 1 calc PR B -1 C4S C 0.0197(5) 0.0125(6) 0.4747(5) 0.0593(16) Uiso 0.25 1 d P . -1 H4SA H 0.0690 -0.0140 0.4853 0.071 Uiso 0.25 1 calc PR . -1 H4SB H 0.0267 0.0685 0.4835 0.071 Uiso 0.25 1 calc PR . -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0231(8) 0.0305(8) 0.0280(10) 0.000 0.000 0.0005(6) C1 0.0194(8) 0.0261(9) 0.0315(11) 0.000 0.000 0.0027(7) C2 0.0238(6) 0.0283(7) 0.0282(8) -0.0021(5) -0.0007(5) 0.0044(5) C3 0.0245(6) 0.0354(7) 0.0282(8) 0.0000(5) 0.0038(5) 0.0016(5) C4 0.0229(9) 0.0348(10) 0.0334(12) 0.000 0.000 0.0007(7) C5 0.0257(7) 0.0318(7) 0.0270(8) -0.0032(5) -0.0001(5) 0.0011(5) C6 0.0261(10) 0.0521(13) 0.0371(13) 0.000 0.000 -0.0069(9) C11 0.0250(7) 0.0343(7) 0.0251(8) 0.0036(5) 0.0014(5) 0.0005(5) C12 0.0311(7) 0.0426(8) 0.0312(9) -0.0003(6) -0.0019(6) -0.0020(6) C13 0.0296(8) 0.0565(10) 0.0430(10) 0.0074(7) -0.0084(7) -0.0029(7) C14 0.0289(7) 0.0497(9) 0.0495(10) 0.0161(7) 0.0012(7) 0.0079(6) C15 0.0394(8) 0.0355(8) 0.0420(10) 0.0076(6) 0.0069(7) 0.0080(6) C16 0.0324(7) 0.0334(7) 0.0313(8) 0.0024(6) -0.0001(6) 0.0020(5) C21 0.0250(7) 0.0425(8) 0.0257(8) -0.0049(6) -0.0017(5) -0.0010(5) C22 0.0289(7) 0.0469(9) 0.0358(9) -0.0092(7) 0.0007(6) 0.0011(6) C23 0.0355(8) 0.0674(12) 0.0388(10) -0.0157(8) 0.0075(7) 0.0005(7) C24 0.0371(8) 0.0765(13) 0.0335(10) -0.0023(8) 0.0087(7) -0.0105(8) C25 0.0423(9) 0.0558(10) 0.0381(10) 0.0041(7) 0.0040(7) -0.0093(7) C26 0.0374(8) 0.0437(8) 0.0343(9) -0.0018(6) 0.0046(6) -0.0021(6) B 0.0331(12) 0.0299(12) 0.0591(18) 0.000 0.000 0.0002(9) Cl1S 0.0591(4) 0.0686(5) 0.0580(5) 0.000 0.000 -0.0037(3) Cl2S 0.2006(17) 0.1558(14) 0.0661(9) 0.000 0.000 0.0073(12) _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 N C1 1.465(2) . ? N B 1.641(3) . ? N H1N 0.929(19) . ? C1 C2 1.3975(17) 10_556 ? C1 C2 1.3975(17) . ? C2 C3 1.3955(19) . ? C2 C5 1.5287(19) . ? C3 C4 1.3887(18) . ? C4 C3 1.3887(18) 10_556 ? C4 C6 1.510(3) . ? C5 C21 1.527(2) . ? C5 C11 1.5349(18) . ? C11 C12 1.390(2) . ? C11 C16 1.392(2) . ? C12 C13 1.390(2) . ? C13 C14 1.383(3) . ? C14 C15 1.380(3) . ? C15 C16 1.392(2) . ? C21 C22 1.390(2) . ? C21 C26 1.392(2) . ? C22 C23 1.387(2) . ? C23 C24 1.381(3) . ? C24 C25 1.379(3) . ? C25 C26 1.389(2) . ? B H1BA 1.13(2) . ? B H1BB 1.20(3) . ? Cl1S C1S 1.941(10) . ? C1S C2S 1.502(7) . ? C2S Cl1S 1.697(11) 9_566 ? Cl2S C3S 1.950(9) . ? C3S C4S 1.518(9) . ? C4S Cl2S 1.677(9) 9_556 ? 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 N B 116.50(15) . . ? B N H1N 107.9(12) . . ? C1 N H1N 108.5(11) . . ? C2 C1 C2 121.66(17) 10_556 . ? C2 C1 N 119.17(8) 10_556 . ? C2 C1 N 119.17(8) . . ? C3 C2 C1 117.94(13) . . ? C3 C2 C5 121.12(12) . . ? C1 C2 C5 120.93(12) . . ? C4 C3 C2 121.72(14) . . ? C3 C4 C3 118.59(18) 10_556 . ? C3 C4 C6 120.71(9) 10_556 . ? C3 C4 C6 120.71(9) . . ? C21 C5 C2 114.09(11) . . ? C21 C5 C11 109.00(11) . . ? C2 C5 C11 112.75(11) . . ? C12 C11 C16 118.89(13) . . ? C12 C11 C5 118.42(13) . . ? C16 C11 C5 122.65(13) . . ? C11 C12 C13 120.69(15) . . ? C14 C13 C12 119.91(15) . . ? C15 C14 C13 119.97(14) . . ? C14 C15 C16 120.24(15) . . ? C11 C16 C15 120.29(15) . . ? C22 C21 C26 118.23(15) . . ? C22 C21 C5 120.09(14) . . ? C26 C21 C5 121.66(13) . . ? C23 C22 C21 120.84(16) . . ? C24 C23 C22 120.24(16) . . ? C25 C24 C23 119.66(17) . . ? C24 C25 C26 120.15(17) . . ? C25 C26 C21 120.86(15) . . ? N B H1BA 105.2(11) . . ? N B H1BB 107.6(17) . . ? H1BA B H1BB 112.2(13) . . ? C2S C1S Cl1S 107.3(4) . . ? C1S C2S Cl1S 105.2(5) . 9_566 ? C4S C3S Cl2S 101.3(5) . . ? C3S C4S Cl2S 112.4(5) . 9_556 ? 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 N C1 C2 89.99(14) . . . 10_556 ? B N C1 C2 -89.99(14) . . . . ? C2 C1 C2 C3 -6.3(3) 10_556 . . . ? N C1 C2 C3 173.66(14) . . . . ? C2 C1 C2 C5 172.70(11) 10_556 . . . ? N C1 C2 C5 -7.3(2) . . . . ? C1 C2 C3 C4 1.0(2) . . . . ? C5 C2 C3 C4 -178.00(15) . . . . ? C2 C3 C4 C3 4.0(3) . . . 10_556 ? C2 C3 C4 C6 -175.98(17) . . . . ? C3 C2 C5 C21 -1.52(18) . . . . ? C1 C2 C5 C21 179.49(14) . . . . ? C3 C2 C5 C11 123.52(14) . . . . ? C1 C2 C5 C11 -55.47(18) . . . . ? C21 C5 C11 C12 -80.59(16) . . . . ? C2 C5 C11 C12 151.64(14) . . . . ? C21 C5 C11 C16 97.00(16) . . . . ? C2 C5 C11 C16 -30.77(19) . . . . ? C16 C11 C12 C13 -0.1(2) . . . . ? C5 C11 C12 C13 177.60(14) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? C5 C11 C16 C15 -177.77(13) . . . . ? C14 C15 C16 C11 0.2(2) . . . . ? C2 C5 C21 C22 -101.00(15) . . . . ? C11 C5 C21 C22 131.99(14) . . . . ? C2 C5 C21 C26 80.79(17) . . . . ? C11 C5 C21 C26 -46.22(18) . . . . ? C26 C21 C22 C23 1.6(2) . . . . ? C5 C21 C22 C23 -176.66(14) . . . . ? C21 C22 C23 C24 -0.8(2) . . . . ? C22 C23 C24 C25 -0.8(3) . . . . ? C23 C24 C25 C26 1.5(3) . . . . ? C24 C25 C26 C21 -0.6(3) . . . . ? C22 C21 C26 C25 -0.9(2) . . . . ? C5 C21 C26 C25 177.32(14) . . . . ? Cl1S C1S C2S Cl1S 179.3(6) . . . 9_566 ? Cl2S C3S C4S Cl2S 177.0(6) . . . 9_556 ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 67.80 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.593 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.044 #===END