# Electronic Supplementary Material (ESI) for Chemical Communications # 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_NS201 _audit_creation_date 2013-07-23 _chemical_name_common Ph2N-BCl2-IPr _chemical_name_systematic ; Diphenylaminodichloroborane-1,3-Bis (2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene ; _chemical_melting_point ? _chemical_formula_moiety 'C39 H46 B Cl2 N3, C7 H8' _chemical_formula_sum 'C46 H54 B Cl2 N3' _chemical_formula_weight 730.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 10.9067(10) _cell_length_b 19.265(2) _cell_length_c 19.688(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4136.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8816 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 21.88 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6316 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details SADABS _exptl_special_details ; THETM01_ALERT_3_ ...Very small, weakly diffracting and air sensitive ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II kappa with CCD area detector' _diffrn_measurement_method 'phi and omega scans, 2deg width' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 99826 _diffrn_reflns_av_R_equivalents 0.1072 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 24.72 _reflns_number_total 7058 _reflns_number_gt 5929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 (Bruker, 2011)' _computing_cell_refinement 'Bruker Apex2 (Bruker, 2011)' _computing_data_reduction 'Bruker SAINT V7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0978P)^2^+0.7538P] 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 0.06(5) _refine_ls_number_reflns 7058 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.72 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.371 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.045 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 B1 B 0.5698(2) 0.41064(16) 0.12257(14) 0.0153(6) Uani 1 1 d . . . C1 C 0.6070(2) 0.48872(12) 0.15059(12) 0.0133(5) Uani 1 1 d . . . C1S C 0.7053(3) 0.27172(15) 0.79182(17) 0.0344(8) Uani 1 1 d . . . C2 C 0.6037(2) 0.60121(13) 0.18134(12) 0.0158(5) Uani 1 1 d . . . H2 H 0.5736 0.6460 0.1926 0.019 Uiso 1 1 calc R . . C2S C 0.7766(3) 0.24312(15) 0.74187(18) 0.0370(8) Uani 1 1 d . . . H2S H 0.8603 0.2331 0.7511 0.044 Uiso 1 1 calc R . . C3 C 0.7213(2) 0.58167(13) 0.18013(13) 0.0170(6) Uani 1 1 d . . . H3 H 0.7904 0.6099 0.1903 0.020 Uiso 1 1 calc R . . C3S C 0.7293(3) 0.22863(17) 0.67852(19) 0.0453(9) Uani 1 1 d . . . H3S H 0.7805 0.2091 0.6445 0.054 Uiso 1 1 calc R . . C4 C 0.8404(2) 0.47647(13) 0.15208(13) 0.0149(6) Uani 1 1 d . . . C4S C 0.6084(4) 0.24228(17) 0.66443(19) 0.0498(10) Uani 1 1 d . . . H4S H 0.5761 0.2333 0.6205 0.060 Uiso 1 1 calc R . . C5 C 0.8986(2) 0.44981(12) 0.20974(13) 0.0174(6) Uani 1 1 d . . . C5S C 0.5341(3) 0.26917(17) 0.7149(2) 0.0423(9) Uani 1 1 d . . . H5S H 0.4497 0.2774 0.7060 0.051 Uiso 1 1 calc R . . C6 C 1.0116(2) 0.41724(14) 0.19916(14) 0.0207(6) Uani 1 1 d . . . H6 H 1.0529 0.3967 0.2366 0.025 Uiso 1 1 calc R . . C6S C 0.5823(3) 0.28406(15) 0.77776(18) 0.0350(8) Uani 1 1 d . . . H6S H 0.5308 0.3030 0.8120 0.042 Uiso 1 1 calc R . . C7 C 1.0643(2) 0.41437(14) 0.13548(15) 0.0249(6) Uani 1 1 d . . . H7 H 1.1403 0.3912 0.1294 0.030 Uiso 1 1 calc R . . C7S C 0.7586(4) 0.2895(2) 0.8600(2) 0.0656(12) Uani 1 1 d . . . H7SA H 0.8211 0.3256 0.8546 0.098 Uiso 1 1 calc R . . H7SB H 0.7960 0.2480 0.8800 0.098 Uiso 1 1 calc R . . H7SC H 0.6934 0.3066 0.8900 0.098 Uiso 1 1 calc R . . C8 C 1.0073(2) 0.44488(14) 0.08082(15) 0.0226(6) Uani 1 1 d . . . H8 H 1.0461 0.4436 0.0376 0.027 Uiso 1 1 calc R . . C9 C 0.8939(2) 0.47759(13) 0.08723(13) 0.0175(6) Uani 1 1 d . . . C10 C 0.8376(2) 0.51673(15) 0.02757(14) 0.0225(6) Uani 1 1 d . . . H10 H 0.7472 0.5197 0.0354 0.027 Uiso 1 1 calc R . . C11 C 0.8881(3) 0.59120(16) 0.02396(15) 0.0327(7) Uani 1 1 d . . . H11A H 0.8701 0.6154 0.0666 0.049 Uiso 1 1 calc R . . H11B H 0.8493 0.6159 -0.0139 0.049 Uiso 1 1 calc R . . H11C H 0.9770 0.5897 0.0169 0.049 Uiso 1 1 calc R . . C12 C 0.8583(3) 0.48052(18) -0.04043(15) 0.0369(8) Uani 1 1 d . . . H12A H 0.8124 0.5048 -0.0760 0.055 Uiso 1 1 calc R . . H12B H 0.8298 0.4324 -0.0375 0.055 Uiso 1 1 calc R . . H12C H 0.9459 0.4811 -0.0515 0.055 Uiso 1 1 calc R . . C13 C 0.8489(2) 0.45963(14) 0.28115(14) 0.0195(6) Uani 1 1 d . . . H13 H 0.7587 0.4681 0.2779 0.023 Uiso 1 1 calc R . . C14 C 0.9088(3) 0.52397(14) 0.31365(14) 0.0237(6) Uani 1 1 d . . . H14A H 0.9976 0.5168 0.3169 0.036 Uiso 1 1 calc R . . H14B H 0.8749 0.5311 0.3592 0.036 Uiso 1 1 calc R . . H14C H 0.8921 0.5649 0.2855 0.036 Uiso 1 1 calc R . . C15 C 0.8696(2) 0.39685(14) 0.32672(14) 0.0239(6) Uani 1 1 d . . . H15A H 0.8373 0.3552 0.3044 0.036 Uiso 1 1 calc R . . H15B H 0.8272 0.4039 0.3701 0.036 Uiso 1 1 calc R . . H15C H 0.9576 0.3910 0.3350 0.036 Uiso 1 1 calc R . . C16 C 0.4021(2) 0.55441(12) 0.15604(12) 0.0131(5) Uani 1 1 d . . . C17 C 0.3572(2) 0.57240(13) 0.09200(13) 0.0171(6) Uani 1 1 d . . . C18 C 0.2334(2) 0.58966(14) 0.08786(14) 0.0216(6) Uani 1 1 d . . . H18 H 0.1992 0.6017 0.0451 0.026 Uiso 1 1 calc R . . C19 C 0.1591(2) 0.58953(14) 0.14481(14) 0.0228(6) Uani 1 1 d . . . H19 H 0.0749 0.6015 0.1408 0.027 Uiso 1 1 calc R . . C20 C 0.2067(2) 0.57218(13) 0.20703(14) 0.0197(6) Uani 1 1 d . . . H20 H 0.1548 0.5728 0.2458 0.024 Uiso 1 1 calc R . . C21 C 0.3299(2) 0.55365(13) 0.21473(14) 0.0167(6) Uani 1 1 d . . . C22 C 0.3780(2) 0.53370(14) 0.28409(13) 0.0224(6) Uani 1 1 d . . . H22 H 0.4653 0.5187 0.2786 0.027 Uiso 1 1 calc R . . C23 C 0.3762(3) 0.59564(17) 0.33285(15) 0.0428(9) Uani 1 1 d . . . H23A H 0.4273 0.6330 0.3145 0.064 Uiso 1 1 calc R . . H23B H 0.4082 0.5813 0.3772 0.064 Uiso 1 1 calc R . . H23C H 0.2918 0.6123 0.3381 0.064 Uiso 1 1 calc R . . C24 C 0.3062(3) 0.47231(18) 0.31303(17) 0.0391(9) Uani 1 1 d . . . H24A H 0.2199 0.4854 0.3184 0.059 Uiso 1 1 calc R . . H24B H 0.3402 0.4594 0.3573 0.059 Uiso 1 1 calc R . . H24C H 0.3124 0.4328 0.2819 0.059 Uiso 1 1 calc R . . C25 C 0.4379(2) 0.57553(14) 0.02936(13) 0.0219(6) Uani 1 1 d . . . H25 H 0.5140 0.5484 0.0393 0.026 Uiso 1 1 calc R . . C26 C 0.4765(3) 0.65036(16) 0.01389(16) 0.0364(8) Uani 1 1 d . . . H26A H 0.4035 0.6783 0.0041 0.055 Uiso 1 1 calc R . . H26B H 0.5312 0.6508 -0.0256 0.055 Uiso 1 1 calc R . . H26C H 0.5193 0.6698 0.0533 0.055 Uiso 1 1 calc R . . C27 C 0.3764(3) 0.54241(18) -0.03200(15) 0.0407(8) Uani 1 1 d . . . H27A H 0.3453 0.4964 -0.0196 0.061 Uiso 1 1 calc R . . H27B H 0.4361 0.5378 -0.0689 0.061 Uiso 1 1 calc R . . H27C H 0.3081 0.5717 -0.0470 0.061 Uiso 1 1 calc R . . C28 C 0.6269(2) 0.33121(13) 0.22084(13) 0.0148(5) Uani 1 1 d . . . C29 C 0.6672(2) 0.26638(13) 0.24488(14) 0.0187(6) Uani 1 1 d . . . H29 H 0.7057 0.2349 0.2145 0.022 Uiso 1 1 calc R . . C30 C 0.6515(2) 0.24767(14) 0.31280(14) 0.0220(6) Uani 1 1 d . . . H30 H 0.6790 0.2034 0.3277 0.026 Uiso 1 1 calc R . . C31 C 0.5970(2) 0.29196(13) 0.35861(14) 0.0229(6) Uani 1 1 d . . . H31 H 0.5873 0.2791 0.4049 0.028 Uiso 1 1 calc R . . C32 C 0.5567(2) 0.35584(14) 0.33530(14) 0.0193(6) Uani 1 1 d . . . H32 H 0.5189 0.3871 0.3662 0.023 Uiso 1 1 calc R . . C33 C 0.5702(2) 0.37521(13) 0.26831(13) 0.0176(6) Uani 1 1 d . . . H33 H 0.5405 0.4192 0.2539 0.021 Uiso 1 1 calc R . . C34 C 0.6896(2) 0.29831(13) 0.10857(13) 0.0166(6) Uani 1 1 d . . . C35 C 0.8154(2) 0.28862(14) 0.10273(15) 0.0242(7) Uani 1 1 d . . . H35 H 0.8699 0.3179 0.1272 0.029 Uiso 1 1 calc R . . C36 C 0.8621(3) 0.23660(15) 0.06142(15) 0.0289(7) Uani 1 1 d . . . H36 H 0.9482 0.2298 0.0585 0.035 Uiso 1 1 calc R . . C37 C 0.7842(3) 0.19474(14) 0.02455(15) 0.0288(7) Uani 1 1 d . . . H37 H 0.8160 0.1594 -0.0041 0.035 Uiso 1 1 calc R . . C38 C 0.6586(3) 0.20486(14) 0.02990(15) 0.0289(7) Uani 1 1 d . . . H38 H 0.6043 0.1764 0.0044 0.035 Uiso 1 1 calc R . . C39 C 0.6116(2) 0.25602(13) 0.07199(13) 0.0212(6) Uani 1 1 d . . . H39 H 0.5254 0.2620 0.0757 0.025 Uiso 1 1 calc R . . Cl1 Cl 0.59119(6) 0.41372(3) 0.02810(3) 0.02587(16) Uani 1 1 d . . . Cl2 Cl 0.39860(5) 0.39777(3) 0.13635(3) 0.01920(14) Uani 1 1 d . . . N1 N 0.72337(17) 0.51275(10) 0.16130(10) 0.0137(5) Uani 1 1 d . . . N2 N 0.53405(17) 0.54438(10) 0.16333(11) 0.0130(5) Uani 1 1 d . . . N3 N 0.64199(17) 0.35127(10) 0.15279(10) 0.0137(5) 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 B1 0.0148(14) 0.0197(16) 0.0114(14) -0.0030(13) 0.0016(11) -0.0019(12) C1 0.0116(11) 0.0162(13) 0.0120(13) 0.0016(10) -0.0003(11) 0.0008(11) C1S 0.0439(19) 0.0212(16) 0.038(2) 0.0106(14) -0.0052(16) -0.0023(14) C2 0.0179(12) 0.0121(13) 0.0173(13) -0.0016(11) 0.0001(11) -0.0001(12) C2S 0.0293(16) 0.0219(17) 0.060(2) 0.0080(16) -0.0039(17) 0.0026(14) C3 0.0184(13) 0.0136(14) 0.0189(14) -0.0014(11) -0.0043(11) -0.0019(11) C3S 0.056(2) 0.0277(19) 0.053(2) 0.0030(16) 0.019(2) -0.0030(17) C4 0.0077(11) 0.0126(13) 0.0243(16) -0.0033(11) 0.0008(11) 0.0011(10) C4S 0.071(3) 0.0312(19) 0.048(2) 0.0025(17) -0.017(2) -0.018(2) C5 0.0138(12) 0.0130(12) 0.0255(15) -0.0023(11) 0.0005(12) -0.0033(11) C5S 0.0289(16) 0.0276(18) 0.070(3) 0.0153(18) -0.0146(18) -0.0061(14) C6 0.0125(12) 0.0185(14) 0.0312(16) 0.0013(12) -0.0074(11) -0.0003(11) C6S 0.0354(18) 0.0187(16) 0.051(2) 0.0049(15) 0.0108(17) -0.0008(13) C7 0.0152(12) 0.0203(15) 0.0391(18) -0.0056(14) 0.0023(12) 0.0009(11) C7S 0.093(3) 0.054(2) 0.050(3) 0.011(2) -0.021(2) -0.001(2) C8 0.0168(13) 0.0243(15) 0.0267(16) -0.0026(13) 0.0038(12) -0.0024(11) C9 0.0134(12) 0.0173(13) 0.0219(15) -0.0074(11) -0.0007(12) -0.0038(11) C10 0.0166(13) 0.0335(16) 0.0176(15) -0.0016(13) 0.0000(12) -0.0002(12) C11 0.0279(15) 0.0427(18) 0.0275(16) 0.0113(15) -0.0027(13) -0.0030(15) C12 0.0284(15) 0.056(2) 0.0261(18) -0.0086(16) -0.0023(13) 0.0066(15) C13 0.0133(12) 0.0191(15) 0.0260(16) 0.0028(12) -0.0036(12) 0.0004(10) C14 0.0252(14) 0.0221(14) 0.0237(15) 0.0001(12) -0.0001(13) -0.0028(13) C15 0.0214(14) 0.0216(15) 0.0288(16) 0.0055(13) -0.0036(11) -0.0030(12) C16 0.0120(11) 0.0094(12) 0.0179(14) -0.0031(10) -0.0008(11) 0.0011(11) C17 0.0207(13) 0.0109(13) 0.0197(15) -0.0042(11) -0.0014(11) -0.0011(10) C18 0.0198(13) 0.0224(15) 0.0224(15) -0.0048(13) -0.0070(12) 0.0030(12) C19 0.0122(12) 0.0221(15) 0.0340(17) -0.0052(14) -0.0028(12) 0.0028(11) C20 0.0150(13) 0.0155(14) 0.0287(17) -0.0005(12) 0.0067(12) -0.0012(11) C21 0.0175(13) 0.0094(13) 0.0232(16) -0.0003(11) 0.0041(11) 0.0008(10) C22 0.0246(14) 0.0238(15) 0.0186(15) 0.0040(12) 0.0039(12) 0.0097(12) C23 0.066(2) 0.042(2) 0.0203(16) -0.0078(15) -0.0097(16) 0.0281(18) C24 0.0279(16) 0.048(2) 0.042(2) 0.0230(17) 0.0165(14) 0.0112(15) C25 0.0221(14) 0.0280(16) 0.0157(14) -0.0033(13) 0.0007(11) 0.0058(11) C26 0.0459(18) 0.0337(18) 0.0296(19) 0.0035(15) 0.0138(15) 0.0041(15) C27 0.0409(18) 0.060(2) 0.0214(17) -0.0129(17) -0.0039(15) 0.0026(16) C28 0.0098(12) 0.0165(13) 0.0182(14) -0.0013(11) -0.0017(10) -0.0026(10) C29 0.0167(13) 0.0133(14) 0.0262(16) -0.0024(12) 0.0013(11) 0.0002(11) C30 0.0249(14) 0.0148(15) 0.0263(17) 0.0049(12) -0.0042(12) -0.0017(11) C31 0.0245(13) 0.0263(15) 0.0180(15) 0.0031(12) 0.0001(13) -0.0038(13) C32 0.0180(13) 0.0208(14) 0.0192(15) -0.0044(12) 0.0008(11) 0.0001(11) C33 0.0179(13) 0.0138(13) 0.0211(15) -0.0013(11) -0.0011(11) 0.0000(10) C34 0.0232(14) 0.0123(13) 0.0143(14) 0.0022(11) 0.0021(11) 0.0009(11) C35 0.0224(15) 0.0202(16) 0.0300(18) 0.0004(13) 0.0017(12) -0.0004(12) C36 0.0290(16) 0.0279(17) 0.0297(18) 0.0045(14) 0.0125(13) 0.0097(13) C37 0.0483(18) 0.0208(15) 0.0172(15) -0.0018(13) 0.0106(15) 0.0124(14) C38 0.0444(18) 0.0210(15) 0.0213(16) -0.0063(13) -0.0046(14) -0.0003(13) C39 0.0245(14) 0.0185(14) 0.0207(15) 0.0011(12) -0.0039(12) 0.0000(12) Cl1 0.0293(3) 0.0233(4) 0.0249(4) -0.0017(3) 0.0001(3) 0.0005(3) Cl2 0.0129(3) 0.0186(3) 0.0261(4) -0.0034(3) -0.0011(3) -0.0011(3) N1 0.0097(10) 0.0148(11) 0.0166(12) -0.0008(9) 0.0003(9) 0.0012(8) N2 0.0119(10) 0.0146(11) 0.0125(11) 0.0005(9) -0.0004(9) 0.0003(9) N3 0.0131(10) 0.0135(11) 0.0146(12) -0.0026(9) 0.0003(9) 0.0023(8) 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 B1 N3 1.510(4) . ? B1 C1 1.653(4) . ? B1 Cl1 1.875(3) . ? B1 Cl2 1.903(3) . ? C1 N2 1.359(3) . ? C1 N1 1.367(3) . ? C1S C2S 1.370(5) . ? C1S C6S 1.391(4) . ? C1S C7S 1.503(5) . ? C2 C3 1.338(3) . ? C2 N2 1.379(3) . ? C2 H2 0.9500 . ? C2S C3S 1.378(5) . ? C2S H2S 0.9500 . ? C3 N1 1.379(3) . ? C3 H3 0.9500 . ? C3S C4S 1.373(5) . ? C3S H3S 0.9500 . ? C4 C5 1.398(4) . ? C4 C9 1.404(4) . ? C4 N1 1.466(3) . ? C4S C5S 1.382(5) . ? C4S H4S 0.9500 . ? C5 C6 1.399(4) . ? C5 C13 1.518(4) . ? C5S C6S 1.376(5) . ? C5S H5S 0.9500 . ? C6 C7 1.380(4) . ? C6 H6 0.9500 . ? C6S H6S 0.9500 . ? C7 C8 1.375(4) . ? C7 H7 0.9500 . ? C7S H7SA 0.9800 . ? C7S H7SB 0.9800 . ? C7S H7SC 0.9800 . ? C8 C9 1.394(4) . ? C8 H8 0.9500 . ? C9 C10 1.525(4) . ? C10 C12 1.526(4) . ? C10 C11 1.538(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.523(4) . ? C13 C14 1.540(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.396(3) . ? C16 C21 1.398(3) . ? C16 N2 1.459(3) . ? C17 C18 1.394(3) . ? C17 C25 1.516(4) . ? C18 C19 1.383(4) . ? C18 H18 0.9500 . ? C19 C20 1.372(4) . ? C19 H19 0.9500 . ? C20 C21 1.399(3) . ? C20 H20 0.9500 . ? C21 C22 1.513(4) . ? C22 C24 1.529(4) . ? C22 C23 1.532(4) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C27 1.522(4) . ? C25 C26 1.532(4) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 N3 1.404(3) . ? C28 C33 1.406(4) . ? C28 C29 1.406(4) . ? C29 C30 1.395(4) . ? C29 H29 0.9500 . ? C30 C31 1.377(4) . ? C30 H30 0.9500 . ? C31 C32 1.385(4) . ? C31 H31 0.9500 . ? C32 C33 1.379(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C39 1.381(4) . ? C34 C35 1.389(4) . ? C34 N3 1.438(3) . ? C35 C36 1.387(4) . ? C35 H35 0.9500 . ? C36 C37 1.378(4) . ? C36 H36 0.9500 . ? C37 C38 1.387(4) . ? C37 H37 0.9500 . ? C38 C39 1.386(4) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 B1 C1 115.4(2) . . ? N3 B1 Cl1 110.48(17) . . ? C1 B1 Cl1 105.76(17) . . ? N3 B1 Cl2 110.89(18) . . ? C1 B1 Cl2 108.18(17) . . ? Cl1 B1 Cl2 105.52(13) . . ? N2 C1 N1 104.4(2) . . ? N2 C1 B1 129.5(2) . . ? N1 C1 B1 126.0(2) . . ? C2S C1S C6S 118.3(3) . . ? C2S C1S C7S 121.0(3) . . ? C6S C1S C7S 120.8(3) . . ? C3 C2 N2 107.5(2) . . ? C3 C2 H2 126.3 . . ? N2 C2 H2 126.3 . . ? C1S C2S C3S 121.2(3) . . ? C1S C2S H2S 119.4 . . ? C3S C2S H2S 119.4 . . ? C2 C3 N1 106.9(2) . . ? C2 C3 H3 126.5 . . ? N1 C3 H3 126.5 . . ? C4S C3S C2S 120.3(3) . . ? C4S C3S H3S 119.9 . . ? C2S C3S H3S 119.9 . . ? C5 C4 C9 123.7(2) . . ? C5 C4 N1 118.0(2) . . ? C9 C4 N1 117.8(2) . . ? C3S C4S C5S 119.3(3) . . ? C3S C4S H4S 120.3 . . ? C5S C4S H4S 120.3 . . ? C4 C5 C6 116.3(2) . . ? C4 C5 C13 123.0(2) . . ? C6 C5 C13 120.5(2) . . ? C6S C5S C4S 120.1(3) . . ? C6S C5S H5S 120.0 . . ? C4S C5S H5S 120.0 . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C5S C6S C1S 120.8(3) . . ? C5S C6S H6S 119.6 . . ? C1S C6S H6S 119.6 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C1S C7S H7SA 109.5 . . ? C1S C7S H7SB 109.5 . . ? H7SA C7S H7SB 109.5 . . ? C1S C7S H7SC 109.5 . . ? H7SA C7S H7SC 109.5 . . ? H7SB C7S H7SC 109.5 . . ? C7 C8 C9 121.6(3) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C9 C4 116.4(2) . . ? C8 C9 C10 120.7(2) . . ? C4 C9 C10 122.7(2) . . ? C9 C10 C12 113.0(2) . . ? C9 C10 C11 110.7(2) . . ? C12 C10 C11 109.5(2) . . ? C9 C10 H10 107.9 . . ? C12 C10 H10 107.9 . . ? C11 C10 H10 107.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 C13 C15 113.2(2) . . ? C5 C13 C14 109.5(2) . . ? C15 C13 C14 109.4(2) . . ? C5 C13 H13 108.2 . . ? C15 C13 H13 108.2 . . ? C14 C13 H13 108.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 123.4(2) . . ? C17 C16 N2 117.9(2) . . ? C21 C16 N2 118.2(2) . . ? C18 C17 C16 116.9(2) . . ? C18 C17 C25 120.4(2) . . ? C16 C17 C25 122.7(2) . . ? C19 C18 C17 121.3(2) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C20 C19 C18 120.2(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 121.5(3) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C16 C21 C20 116.7(2) . . ? C16 C21 C22 123.6(2) . . ? C20 C21 C22 119.7(2) . . ? C21 C22 C24 110.8(2) . . ? C21 C22 C23 111.3(2) . . ? C24 C22 C23 111.2(3) . . ? C21 C22 H22 107.8 . . ? C24 C22 H22 107.8 . . ? C23 C22 H22 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C17 C25 C27 111.9(2) . . ? C17 C25 C26 111.0(2) . . ? C27 C25 C26 111.0(3) . . ? C17 C25 H25 107.6 . . ? C27 C25 H25 107.6 . . ? C26 C25 H25 107.6 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C28 C33 121.3(2) . . ? N3 C28 C29 122.0(2) . . ? C33 C28 C29 116.7(2) . . ? C30 C29 C28 120.9(2) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C31 C30 C29 121.4(3) . . ? C31 C30 H30 119.3 . . ? C29 C30 H30 119.3 . . ? C30 C31 C32 118.1(3) . . ? C30 C31 H31 121.0 . . ? C32 C31 H31 121.0 . . ? C33 C32 C31 121.6(2) . . ? C33 C32 H32 119.2 . . ? C31 C32 H32 119.2 . . ? C32 C33 C28 121.3(2) . . ? C32 C33 H33 119.3 . . ? C28 C33 H33 119.3 . . ? C39 C34 C35 119.1(3) . . ? C39 C34 N3 120.8(2) . . ? C35 C34 N3 120.1(2) . . ? C36 C35 C34 120.5(3) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C37 C36 C35 120.3(3) . . ? C37 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C36 C37 C38 119.1(3) . . ? C36 C37 H37 120.4 . . ? C38 C37 H37 120.4 . . ? C39 C38 C37 120.7(3) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C34 C39 C38 120.2(3) . . ? C34 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? C1 N1 C3 110.7(2) . . ? C1 N1 C4 128.86(19) . . ? C3 N1 C4 120.41(19) . . ? C1 N2 C2 110.59(18) . . ? C1 N2 C16 131.6(2) . . ? C2 N2 C16 117.6(2) . . ? C28 N3 C34 115.1(2) . . ? C28 N3 B1 121.56(19) . . ? C34 N3 B1 119.1(2) . . ? 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 N3 B1 C1 N2 -143.0(2) . . . . ? Cl1 B1 C1 N2 94.5(3) . . . . ? Cl2 B1 C1 N2 -18.2(3) . . . . ? N3 B1 C1 N1 42.3(3) . . . . ? Cl1 B1 C1 N1 -80.2(3) . . . . ? Cl2 B1 C1 N1 167.2(2) . . . . ? C6S C1S C2S C3S 1.9(4) . . . . ? C7S C1S C2S C3S -178.0(3) . . . . ? N2 C2 C3 N1 0.0(3) . . . . ? C1S C2S C3S C4S -0.5(5) . . . . ? C2S C3S C4S C5S -1.5(5) . . . . ? C9 C4 C5 C6 -5.9(4) . . . . ? N1 C4 C5 C6 -178.3(2) . . . . ? C9 C4 C5 C13 169.5(2) . . . . ? N1 C4 C5 C13 -2.8(3) . . . . ? C3S C4S C5S C6S 2.0(5) . . . . ? C4 C5 C6 C7 2.5(4) . . . . ? C13 C5 C6 C7 -173.0(2) . . . . ? C4S C5S C6S C1S -0.7(5) . . . . ? C2S C1S C6S C5S -1.3(4) . . . . ? C7S C1S C6S C5S 178.6(3) . . . . ? C5 C6 C7 C8 1.2(4) . . . . ? C6 C7 C8 C9 -1.9(4) . . . . ? C7 C8 C9 C4 -1.2(4) . . . . ? C7 C8 C9 C10 174.4(2) . . . . ? C5 C4 C9 C8 5.3(4) . . . . ? N1 C4 C9 C8 177.6(2) . . . . ? C5 C4 C9 C10 -170.2(2) . . . . ? N1 C4 C9 C10 2.1(3) . . . . ? C8 C9 C10 C12 38.8(3) . . . . ? C4 C9 C10 C12 -145.8(2) . . . . ? C8 C9 C10 C11 -84.3(3) . . . . ? C4 C9 C10 C11 91.0(3) . . . . ? C4 C5 C13 C15 143.9(2) . . . . ? C6 C5 C13 C15 -40.8(3) . . . . ? C4 C5 C13 C14 -93.8(3) . . . . ? C6 C5 C13 C14 81.5(3) . . . . ? C21 C16 C17 C18 -0.6(4) . . . . ? N2 C16 C17 C18 -172.7(2) . . . . ? C21 C16 C17 C25 177.7(2) . . . . ? N2 C16 C17 C25 5.6(3) . . . . ? C16 C17 C18 C19 0.6(4) . . . . ? C25 C17 C18 C19 -177.7(2) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? C18 C19 C20 C21 -0.6(4) . . . . ? C17 C16 C21 C20 0.0(4) . . . . ? N2 C16 C21 C20 172.1(2) . . . . ? C17 C16 C21 C22 179.5(2) . . . . ? N2 C16 C21 C22 -8.4(4) . . . . ? C19 C20 C21 C16 0.6(4) . . . . ? C19 C20 C21 C22 -179.0(2) . . . . ? C16 C21 C22 C24 -121.6(3) . . . . ? C20 C21 C22 C24 57.9(3) . . . . ? C16 C21 C22 C23 114.1(3) . . . . ? C20 C21 C22 C23 -66.4(3) . . . . ? C18 C17 C25 C27 -45.4(3) . . . . ? C16 C17 C25 C27 136.4(3) . . . . ? C18 C17 C25 C26 79.2(3) . . . . ? C16 C17 C25 C26 -99.0(3) . . . . ? N3 C28 C29 C30 179.8(2) . . . . ? C33 C28 C29 C30 -0.4(3) . . . . ? C28 C29 C30 C31 -0.4(4) . . . . ? C29 C30 C31 C32 0.6(4) . . . . ? C30 C31 C32 C33 0.0(4) . . . . ? C31 C32 C33 C28 -0.9(4) . . . . ? N3 C28 C33 C32 -179.2(2) . . . . ? C29 C28 C33 C32 1.0(3) . . . . ? C39 C34 C35 C36 -0.8(4) . . . . ? N3 C34 C35 C36 178.5(2) . . . . ? C34 C35 C36 C37 1.3(4) . . . . ? C35 C36 C37 C38 -0.7(4) . . . . ? C36 C37 C38 C39 -0.4(4) . . . . ? C35 C34 C39 C38 -0.2(4) . . . . ? N3 C34 C39 C38 -179.6(2) . . . . ? C37 C38 C39 C34 0.9(4) . . . . ? N2 C1 N1 C3 0.0(3) . . . . ? B1 C1 N1 C3 175.7(2) . . . . ? N2 C1 N1 C4 -176.8(2) . . . . ? B1 C1 N1 C4 -1.0(4) . . . . ? C2 C3 N1 C1 0.0(3) . . . . ? C2 C3 N1 C4 177.1(2) . . . . ? C5 C4 N1 C1 -100.7(3) . . . . ? C9 C4 N1 C1 86.5(3) . . . . ? C5 C4 N1 C3 82.8(3) . . . . ? C9 C4 N1 C3 -90.0(3) . . . . ? N1 C1 N2 C2 0.1(3) . . . . ? B1 C1 N2 C2 -175.5(2) . . . . ? N1 C1 N2 C16 174.6(2) . . . . ? B1 C1 N2 C16 -0.9(4) . . . . ? C3 C2 N2 C1 -0.1(3) . . . . ? C3 C2 N2 C16 -175.5(2) . . . . ? C17 C16 N2 C1 -83.4(3) . . . . ? C21 C16 N2 C1 104.1(3) . . . . ? C17 C16 N2 C2 90.8(3) . . . . ? C21 C16 N2 C2 -81.7(3) . . . . ? C33 C28 N3 C34 -173.7(2) . . . . ? C29 C28 N3 C34 6.1(3) . . . . ? C33 C28 N3 B1 -16.9(3) . . . . ? C29 C28 N3 B1 162.9(2) . . . . ? C39 C34 N3 C28 93.4(3) . . . . ? C35 C34 N3 C28 -85.9(3) . . . . ? C39 C34 N3 B1 -64.0(3) . . . . ? C35 C34 N3 B1 116.7(3) . . . . ? C1 B1 N3 C28 69.9(3) . . . . ? Cl1 B1 N3 C28 -170.16(17) . . . . ? Cl2 B1 N3 C28 -53.5(3) . . . . ? C1 B1 N3 C34 -134.2(2) . . . . ? Cl1 B1 N3 C34 -14.3(3) . . . . ? Cl2 B1 N3 C34 102.4(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 953007'