Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Alan Cowley' _publ_contact_author_address ; Chemistry and Biochemistry The University of Texas at Austin 1 University Station A5300 Austin Texas 78712 UNITED STATES OF AMERICA ; _publ_contact_author_email COWLEY@MAIL.UTEXAS.EDU _publ_section_title ; Synthesis and structure of two new (guanidinate)boron dichlorides and their attempted conversion to boron(I) derivatives ; loop_ _publ_author_name 'A. Cowley' 'Michael Findlater' 'Nicholas J. Hill' data_1 _database_code_depnum_ccdc_archive 'CCDC 645034' _chemical_formula_moiety 'C25 H34 N2 S1' _chemical_formula_sum 'C25 H34 N2 S1' _chemical_formula_weight 394.6 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.444(5) _cell_length_b 14.858(5) _cell_length_c 18.332(5) _cell_angle_alpha 90 _cell_angle_beta 122.823(5) _cell_angle_gamma 90 _cell_volume 5824(3) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 11537 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 0.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_reflns_number 11539 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6671 _reflns_number_gt 4104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1522P)^2^+0.9429P] 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_number_reflns 6671 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.2374 _refine_ls_wR_factor_gt 0.2171 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 C1 C 0.89130(11) 0.07246(14) 0.65988(14) 0.0282(5) Uani 1 1 d . . . C2 C 0.90934(11) 0.10819(16) 0.54315(14) 0.0326(5) Uani 1 1 d . . . C3 C 0.89048(12) 0.04429(18) 0.47770(17) 0.0413(6) Uani 1 1 d . . . C4 C 0.87636(14) 0.0750(2) 0.39696(17) 0.0522(8) Uani 1 1 d . . . H4 H 0.8628 0.0331 0.3510 0.063 Uiso 1 1 calc R . . C5 C 0.88152(15) 0.1642(2) 0.38231(18) 0.0573(8) Uani 1 1 d . . . H5 H 0.8724 0.1827 0.3270 0.069 Uiso 1 1 calc R . . C6 C 0.90010(14) 0.2284(2) 0.44829(17) 0.0499(7) Uani 1 1 d . . . H6 H 0.9032 0.2901 0.4375 0.060 Uiso 1 1 calc R . . C7 C 0.91400(12) 0.20086(17) 0.53011(15) 0.0365(6) Uani 1 1 d . . . C8 C 0.88877(14) -0.0553(2) 0.49468(19) 0.0501(7) Uani 1 1 d . . . H8 H 0.8900 -0.0613 0.5499 0.060 Uiso 1 1 calc R . . C9 C 0.8280(2) -0.1008(3) 0.4215(3) 0.0841(12) Uani 1 1 d . . . H9A H 0.7917 -0.0687 0.4138 0.126 Uiso 1 1 calc R . . H9B H 0.8270 -0.1635 0.4373 0.126 Uiso 1 1 calc R . . H9C H 0.8269 -0.0991 0.3673 0.126 Uiso 1 1 calc R . . C10 C 0.94731(19) -0.1005(2) 0.5081(3) 0.0746(10) Uani 1 1 d . . . H10A H 0.9473 -0.0956 0.4547 0.112 Uiso 1 1 calc R . . H10B H 0.9477 -0.1641 0.5224 0.112 Uiso 1 1 calc R . . H10C H 0.9846 -0.0707 0.5557 0.112 Uiso 1 1 calc R . . C11 C 0.93577(13) 0.26813(17) 0.60226(17) 0.0423(6) Uani 1 1 d . . . H11 H 0.9273 0.2424 0.6453 0.051 Uiso 1 1 calc R . . C12 C 1.00577(15) 0.2827(2) 0.6483(2) 0.0548(8) Uani 1 1 d . . . H12A H 1.0278 0.2282 0.6805 0.082 Uiso 1 1 calc R . . H12B H 1.0183 0.3333 0.6887 0.082 Uiso 1 1 calc R . . H12C H 1.0164 0.2960 0.6054 0.082 Uiso 1 1 calc R . . C13 C 0.90050(16) 0.3580(2) 0.5700(2) 0.0596(8) Uani 1 1 d . . . H13A H 0.9136 0.3897 0.5356 0.089 Uiso 1 1 calc R . . H13B H 0.9100 0.3951 0.6199 0.089 Uiso 1 1 calc R . . H13C H 0.8554 0.3464 0.5340 0.089 Uiso 1 1 calc R . . C14 C 0.78464(11) 0.09000(15) 0.62761(15) 0.0324(5) Uani 1 1 d . . . C15 C 0.74954(13) 0.01202(17) 0.60719(18) 0.0417(6) Uani 1 1 d . . . C16 C 0.70614(13) 0.0055(2) 0.6310(2) 0.0496(7) Uani 1 1 d . . . H16 H 0.6816 -0.0474 0.6175 0.060 Uiso 1 1 calc R . . C17 C 0.69864(13) 0.07646(19) 0.67443(19) 0.0468(7) Uani 1 1 d . . . H17 H 0.6694 0.0715 0.6912 0.056 Uiso 1 1 calc R . . C18 C 0.73375(12) 0.15400(19) 0.69314(16) 0.0429(6) Uani 1 1 d . . . H18 H 0.7280 0.2021 0.7223 0.051 Uiso 1 1 calc R . . C19 C 0.77734(11) 0.16282(16) 0.66996(15) 0.0342(5) Uani 1 1 d . . . C20 C 0.75585(14) -0.06647(18) 0.5599(2) 0.0495(7) Uani 1 1 d . . . H20 H 0.7908 -0.0517 0.5520 0.059 Uiso 1 1 calc R . . C21 C 0.7733(2) -0.1527(2) 0.6112(3) 0.0825(12) Uani 1 1 d . . . H21A H 0.8080 -0.1413 0.6710 0.124 Uiso 1 1 calc R . . H21B H 0.7861 -0.1976 0.5846 0.124 Uiso 1 1 calc R . . H21C H 0.7372 -0.1753 0.6114 0.124 Uiso 1 1 calc R . . C22 C 0.6974(2) -0.0795(3) 0.4696(2) 0.0775(11) Uani 1 1 d . . . H22A H 0.7054 -0.1255 0.4385 0.116 Uiso 1 1 calc R . . H22B H 0.6866 -0.0226 0.4376 0.116 Uiso 1 1 calc R . . H22C H 0.6627 -0.0988 0.4747 0.116 Uiso 1 1 calc R . . C23 C 0.81252(13) 0.25137(16) 0.68739(16) 0.0388(6) Uani 1 1 d . . . H23 H 0.8515 0.2380 0.6886 0.047 Uiso 1 1 calc R . . C24 C 0.77507(17) 0.3170(2) 0.6150(2) 0.0598(8) Uani 1 1 d . . . H24A H 0.7664 0.2912 0.5603 0.090 Uiso 1 1 calc R . . H24B H 0.7988 0.3730 0.6271 0.090 Uiso 1 1 calc R . . H24C H 0.7356 0.3298 0.6103 0.090 Uiso 1 1 calc R . . C25 C 0.83248(18) 0.2945(2) 0.7742(2) 0.0641(9) Uani 1 1 d . . . H25A H 0.7953 0.3126 0.7738 0.096 Uiso 1 1 calc R . . H25B H 0.8583 0.3476 0.7836 0.096 Uiso 1 1 calc R . . H25C H 0.8567 0.2511 0.8211 0.096 Uiso 1 1 calc R . . N1 N 0.92892(9) 0.07888(13) 0.62936(12) 0.0317(5) Uani 1 1 d . . . N2 N 0.83081(9) 0.09690(12) 0.60499(12) 0.0301(4) Uani 1 1 d . . . S1 S 0.91888(3) 0.03596(4) 0.76134(4) 0.0368(2) 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 C1 0.0256(12) 0.0302(11) 0.0250(11) -0.0008(8) 0.0112(10) -0.0022(9) C2 0.0259(12) 0.0480(14) 0.0237(11) 0.0016(9) 0.0133(10) 0.0038(10) C3 0.0322(14) 0.0589(16) 0.0335(13) -0.0063(11) 0.0181(12) 0.0082(11) C4 0.0429(16) 0.082(2) 0.0270(13) -0.0054(13) 0.0161(12) 0.0186(15) C5 0.0511(18) 0.097(2) 0.0267(13) 0.0141(14) 0.0230(13) 0.0243(17) C6 0.0469(17) 0.0693(18) 0.0364(15) 0.0157(13) 0.0244(14) 0.0152(14) C7 0.0307(13) 0.0522(14) 0.0292(12) 0.0026(10) 0.0179(11) 0.0025(11) C8 0.0439(17) 0.0607(17) 0.0425(15) -0.0171(13) 0.0213(14) -0.0023(13) C9 0.077(3) 0.089(2) 0.069(2) -0.039(2) 0.028(2) -0.026(2) C10 0.073(3) 0.0596(19) 0.099(3) -0.0064(18) 0.052(2) 0.0114(17) C11 0.0488(17) 0.0455(14) 0.0355(13) 0.0034(11) 0.0246(13) 0.0002(12) C12 0.0439(17) 0.0588(17) 0.0487(17) 0.0019(13) 0.0167(14) 0.0022(13) C13 0.056(2) 0.0524(16) 0.066(2) 0.0013(14) 0.0296(17) 0.0041(14) C14 0.0248(12) 0.0411(13) 0.0293(12) 0.0102(9) 0.0134(10) 0.0054(10) C15 0.0348(14) 0.0452(14) 0.0433(14) 0.0094(11) 0.0200(12) 0.0038(11) C16 0.0374(15) 0.0534(16) 0.0622(19) 0.0140(14) 0.0298(15) -0.0017(13) C17 0.0391(16) 0.0546(16) 0.0557(17) 0.0151(13) 0.0316(14) 0.0073(13) C18 0.0372(15) 0.0552(16) 0.0395(14) 0.0064(11) 0.0229(13) 0.0072(12) C19 0.0256(12) 0.0440(13) 0.0284(12) 0.0068(10) 0.0116(10) 0.0045(10) C20 0.0426(16) 0.0477(15) 0.0596(18) -0.0080(13) 0.0287(15) -0.0100(13) C21 0.100(3) 0.0527(19) 0.074(2) 0.0025(17) 0.033(2) 0.0124(19) C22 0.078(3) 0.072(2) 0.055(2) -0.0037(17) 0.0176(19) 0.0052(19) C23 0.0368(14) 0.0395(13) 0.0422(14) -0.0026(10) 0.0228(12) 0.0008(11) C24 0.062(2) 0.0531(16) 0.0582(18) 0.0109(14) 0.0287(17) -0.0006(15) C25 0.074(2) 0.070(2) 0.059(2) -0.0193(16) 0.0420(19) -0.0200(17) N1 0.0272(11) 0.0425(11) 0.0235(10) 0.0000(8) 0.0126(9) 0.0011(8) N2 0.0242(10) 0.0358(10) 0.0274(9) 0.0010(7) 0.0122(8) 0.0011(8) S1 0.0296(3) 0.0494(4) 0.0275(3) 0.0094(2) 0.0129(3) 0.0011(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 C1 N1 1.349(3) . ? C1 N2 1.355(3) . ? C1 S1 1.683(2) . ? C2 C3 1.395(3) . ? C2 C7 1.413(4) . ? C2 N1 1.443(3) . ? C3 C4 1.397(4) . ? C3 C8 1.518(4) . ? C4 C5 1.372(5) . ? C4 H4 0.9500 . ? C5 C6 1.407(4) . ? C5 H5 0.9500 . ? C6 C7 1.403(3) . ? C6 H6 0.9500 . ? C7 C11 1.504(4) . ? C8 C10 1.527(5) . ? C8 C9 1.548(4) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.517(4) . ? C11 C13 1.537(4) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.385(4) . ? C14 C19 1.402(3) . ? C14 N2 1.446(3) . ? C15 C16 1.393(4) . ? C15 C20 1.513(4) . ? C16 C17 1.396(4) . ? C16 H16 0.9500 . ? C17 C18 1.382(4) . ? C17 H17 0.9500 . ? C18 C19 1.392(4) . ? C18 H18 0.9500 . ? C19 C23 1.525(4) . ? C20 C21 1.508(4) . ? C20 C22 1.523(5) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.500(4) . ? C23 C25 1.526(4) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 116.68(19) . . ? N1 C1 S1 121.13(17) . . ? N2 C1 S1 122.19(17) . . ? C3 C2 C7 122.6(2) . . ? C3 C2 N1 119.3(2) . . ? C7 C2 N1 117.9(2) . . ? C2 C3 C4 117.4(3) . . ? C2 C3 C8 121.5(2) . . ? C4 C3 C8 121.1(2) . . ? C5 C4 C3 121.7(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.6(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C2 118.0(2) . . ? C6 C7 C11 120.4(2) . . ? C2 C7 C11 121.6(2) . . ? C3 C8 C10 109.1(3) . . ? C3 C8 C9 112.0(3) . . ? C10 C8 C9 112.1(3) . . ? C3 C8 H8 107.8 . . ? C10 C8 H8 107.8 . . ? C9 C8 H8 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 C12 110.2(2) . . ? C7 C11 C13 112.3(2) . . ? C12 C11 C13 110.8(2) . . ? C7 C11 H11 107.8 . . ? C12 C11 H11 107.8 . . ? C13 C11 H11 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 122.4(2) . . ? C15 C14 N2 119.1(2) . . ? C19 C14 N2 118.4(2) . . ? C14 C15 C16 118.6(3) . . ? C14 C15 C20 123.1(2) . . ? C16 C15 C20 118.3(3) . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 120.1(2) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 121.2(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C14 117.6(2) . . ? C18 C19 C23 119.4(2) . . ? C14 C19 C23 122.9(2) . . ? C21 C20 C15 112.6(3) . . ? C21 C20 C22 110.8(3) . . ? C15 C20 C22 112.1(3) . . ? C21 C20 H20 107.0 . . ? C15 C20 H20 107.0 . . ? C22 C20 H20 107.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C25 110.0(2) . . ? C24 C23 C19 110.9(2) . . ? C25 C23 C19 114.0(2) . . ? C24 C23 H23 107.2 . . ? C25 C23 H23 107.2 . . ? C19 C23 H23 107.2 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C1 N1 C2 125.05(19) . . ? C1 N2 C14 122.72(18) . . ? 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 C7 C2 C3 C4 0.4(4) . . . . ? N1 C2 C3 C4 -175.4(2) . . . . ? C7 C2 C3 C8 177.1(2) . . . . ? N1 C2 C3 C8 1.3(4) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C8 C3 C4 C5 -175.8(3) . . . . ? C3 C4 C5 C6 -1.4(5) . . . . ? C4 C5 C6 C7 0.5(4) . . . . ? C5 C6 C7 C2 0.7(4) . . . . ? C5 C6 C7 C11 178.2(3) . . . . ? C3 C2 C7 C6 -1.2(4) . . . . ? N1 C2 C7 C6 174.6(2) . . . . ? C3 C2 C7 C11 -178.7(2) . . . . ? N1 C2 C7 C11 -2.8(3) . . . . ? C2 C3 C8 C10 -99.9(3) . . . . ? C4 C3 C8 C10 76.7(4) . . . . ? C2 C3 C8 C9 135.4(3) . . . . ? C4 C3 C8 C9 -48.1(4) . . . . ? C6 C7 C11 C12 -84.2(3) . . . . ? C2 C7 C11 C12 93.2(3) . . . . ? C6 C7 C11 C13 39.9(3) . . . . ? C2 C7 C11 C13 -142.8(3) . . . . ? C19 C14 C15 C16 -1.0(4) . . . . ? N2 C14 C15 C16 178.7(2) . . . . ? C19 C14 C15 C20 178.7(2) . . . . ? N2 C14 C15 C20 -1.6(4) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? C20 C15 C16 C17 -179.8(3) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C16 C17 C18 C19 -0.5(4) . . . . ? C17 C18 C19 C14 -0.5(4) . . . . ? C17 C18 C19 C23 176.7(2) . . . . ? C15 C14 C19 C18 1.3(3) . . . . ? N2 C14 C19 C18 -178.4(2) . . . . ? C15 C14 C19 C23 -175.8(2) . . . . ? N2 C14 C19 C23 4.5(3) . . . . ? C14 C15 C20 C21 121.5(3) . . . . ? C16 C15 C20 C21 -58.8(4) . . . . ? C14 C15 C20 C22 -112.8(3) . . . . ? C16 C15 C20 C22 66.9(4) . . . . ? C18 C19 C23 C24 -84.9(3) . . . . ? C14 C19 C23 C24 92.2(3) . . . . ? C18 C19 C23 C25 40.0(3) . . . . ? C14 C19 C23 C25 -143.0(3) . . . . ? N2 C1 N1 C2 -1.0(3) . . . . ? S1 C1 N1 C2 179.11(17) . . . . ? C3 C2 N1 C1 -92.9(3) . . . . ? C7 C2 N1 C1 91.1(3) . . . . ? N1 C1 N2 C14 177.4(2) . . . . ? S1 C1 N2 C14 -2.7(3) . . . . ? C15 C14 N2 C1 -91.6(3) . . . . ? C19 C14 N2 C1 88.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.469 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.075 # Attachment 'compound13.cif' data_mfnh090 _database_code_depnum_ccdc_archive 'CCDC 645035' _chemical_formula_moiety 'C25 H34 N2' _chemical_formula_sum 'C25 H34 N2' _chemical_formula_weight 362.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0454(18) _cell_length_b 13.424(3) _cell_length_c 18.684(4) _cell_angle_alpha 90 _cell_angle_beta 102.93(3) _cell_angle_gamma 90 _cell_volume 2211.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4989 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.43 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_reflns_number 8257 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.1127 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.43 _reflns_number_total 4989 _reflns_number_gt 2375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4989 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1488 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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 C1 C 0.44630(19) 0.19458(15) 0.37292(11) 0.0297(5) Uani 1 1 d . . . C2 C 0.4729(2) 0.27090(14) 0.49486(10) 0.0311(5) Uani 1 1 d . . . C3 C 0.5910(2) 0.21523(15) 0.53890(10) 0.0335(5) Uani 1 1 d . . . C4 C 0.6296(2) 0.23909(16) 0.61328(11) 0.0416(6) Uani 1 1 d . . . H4 H 0.7086 0.2031 0.6448 0.050 Uiso 1 1 calc R . . C5 C 0.5558(2) 0.31383(17) 0.64225(11) 0.0461(6) Uani 1 1 d . . . H5 H 0.5842 0.3284 0.6932 0.055 Uiso 1 1 calc R . . C6 C 0.4414(2) 0.36732(16) 0.59777(11) 0.0422(6) Uani 1 1 d . . . H6 H 0.3919 0.4187 0.6184 0.051 Uiso 1 1 calc R . . C7 C 0.3970(2) 0.34721(15) 0.52305(10) 0.0346(5) Uani 1 1 d . . . C8 C 0.6746(2) 0.13558(15) 0.50680(10) 0.0378(5) Uani 1 1 d . . . H8 H 0.5986 0.1011 0.4676 0.045 Uiso 1 1 calc R . . C9 C 0.7482(3) 0.05626(17) 0.56196(12) 0.0581(7) Uani 1 1 d . . . H9A H 0.8310 0.0862 0.5985 0.087 Uiso 1 1 calc R . . H9B H 0.7884 0.0027 0.5362 0.087 Uiso 1 1 calc R . . H9C H 0.6722 0.0289 0.5866 0.087 Uiso 1 1 calc R . . C10 C 0.7928(2) 0.18196(19) 0.47013(13) 0.0550(7) Uani 1 1 d . . . H10A H 0.7442 0.2324 0.4347 0.082 Uiso 1 1 calc R . . H10B H 0.8373 0.1300 0.4446 0.082 Uiso 1 1 calc R . . H10C H 0.8726 0.2132 0.5075 0.082 Uiso 1 1 calc R . . C11 C 0.2672(2) 0.40323(16) 0.47385(11) 0.0430(6) Uani 1 1 d . . . H11 H 0.2866 0.4038 0.4232 0.052 Uiso 1 1 calc R . . C12 C 0.1190(3) 0.34795(19) 0.47015(16) 0.0729(8) Uani 1 1 d . . . H12A H 0.1299 0.2787 0.4556 0.109 Uiso 1 1 calc R . . H12B H 0.0378 0.3801 0.4340 0.109 Uiso 1 1 calc R . . H12C H 0.0937 0.3494 0.5185 0.109 Uiso 1 1 calc R . . C13 C 0.2528(3) 0.51105(17) 0.49647(14) 0.0606(7) Uani 1 1 d . . . H13A H 0.2255 0.5130 0.5444 0.091 Uiso 1 1 calc R . . H13B H 0.1737 0.5443 0.4598 0.091 Uiso 1 1 calc R . . H13C H 0.3497 0.5453 0.4998 0.091 Uiso 1 1 calc R . . C14 C 0.3899(2) 0.06589(14) 0.28054(9) 0.0311(5) Uani 1 1 d . . . C15 C 0.4772(2) -0.01594(15) 0.26831(10) 0.0336(5) Uani 1 1 d . . . C16 C 0.4011(2) -0.09637(16) 0.22892(11) 0.0412(5) Uani 1 1 d . . . H16 H 0.4570 -0.1534 0.2206 0.049 Uiso 1 1 calc R . . C17 C 0.2466(2) -0.09429(16) 0.20206(11) 0.0435(6) Uani 1 1 d . . . H17 H 0.1965 -0.1502 0.1763 0.052 Uiso 1 1 calc R . . C18 C 0.1641(2) -0.01077(16) 0.21251(11) 0.0423(6) Uani 1 1 d . . . H18 H 0.0578 -0.0096 0.1927 0.051 Uiso 1 1 calc R . . C19 C 0.2329(2) 0.07074(15) 0.25107(10) 0.0344(5) Uani 1 1 d . . . C20 C 0.6480(2) -0.01874(16) 0.29753(11) 0.0406(5) Uani 1 1 d . . . H20 H 0.6824 0.0509 0.3109 0.049 Uiso 1 1 calc R . . C21 C 0.7307(3) -0.05504(18) 0.23941(14) 0.0583(7) Uani 1 1 d . . . H21A H 0.6973 -0.1228 0.2242 0.087 Uiso 1 1 calc R . . H21B H 0.8403 -0.0550 0.2600 0.087 Uiso 1 1 calc R . . H21C H 0.7074 -0.0106 0.1968 0.087 Uiso 1 1 calc R . . C22 C 0.6901(2) -0.08187(18) 0.36708(13) 0.0587(7) Uani 1 1 d . . . H22A H 0.6354 -0.0575 0.4033 0.088 Uiso 1 1 calc R . . H22B H 0.7996 -0.0772 0.3875 0.088 Uiso 1 1 calc R . . H22C H 0.6625 -0.1515 0.3551 0.088 Uiso 1 1 calc R . . C23 C 0.1399(2) 0.16269(16) 0.25964(11) 0.0423(6) Uani 1 1 d . . . H23 H 0.2134 0.2172 0.2789 0.051 Uiso 1 1 calc R . . C24 C 0.0437(3) 0.1462(2) 0.31605(15) 0.0715(8) Uani 1 1 d . . . H24A H -0.0100 0.2079 0.3223 0.107 Uiso 1 1 calc R . . H24B H 0.1094 0.1270 0.3632 0.107 Uiso 1 1 calc R . . H24C H -0.0302 0.0931 0.2990 0.107 Uiso 1 1 calc R . . C25 C 0.0434(3) 0.1986(2) 0.18692(14) 0.0731(8) Uani 1 1 d . . . H25A H 0.1073 0.2067 0.1513 0.110 Uiso 1 1 calc R . . H25B H -0.0032 0.2626 0.1941 0.110 Uiso 1 1 calc R . . H25C H -0.0362 0.1495 0.1684 0.110 Uiso 1 1 calc R . . N1 N 0.42636(17) 0.25471(12) 0.41826(9) 0.0341(4) Uani 1 1 d . . . N2 N 0.46880(17) 0.14769(12) 0.32035(9) 0.0328(4) 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 C1 0.0281(10) 0.0289(12) 0.0304(11) 0.0051(10) 0.0028(9) -0.0009(9) C2 0.0340(10) 0.0340(12) 0.0248(10) -0.0014(9) 0.0052(8) -0.0059(9) C3 0.0324(10) 0.0392(13) 0.0293(11) 0.0005(9) 0.0076(9) -0.0034(9) C4 0.0389(11) 0.0525(15) 0.0298(12) 0.0024(11) 0.0001(9) -0.0035(10) C5 0.0534(13) 0.0570(15) 0.0267(11) -0.0072(11) 0.0062(10) -0.0050(12) C6 0.0510(13) 0.0461(14) 0.0306(12) -0.0081(10) 0.0111(10) -0.0004(10) C7 0.0396(11) 0.0361(12) 0.0296(11) -0.0009(9) 0.0107(9) -0.0048(9) C8 0.0391(11) 0.0434(13) 0.0292(11) 0.0028(10) 0.0041(9) 0.0018(10) C9 0.0662(15) 0.0604(17) 0.0448(14) 0.0070(12) 0.0061(11) 0.0201(13) C10 0.0465(13) 0.0693(17) 0.0515(14) -0.0016(13) 0.0160(11) 0.0006(12) C11 0.0535(13) 0.0449(14) 0.0315(11) -0.0012(10) 0.0113(10) 0.0116(11) C12 0.0507(14) 0.0604(18) 0.093(2) -0.0010(16) -0.0153(13) 0.0019(13) C13 0.0633(15) 0.0449(15) 0.0721(17) 0.0031(13) 0.0122(13) 0.0079(12) C14 0.0399(11) 0.0314(12) 0.0210(10) -0.0003(9) 0.0046(8) -0.0063(10) C15 0.0425(11) 0.0321(12) 0.0269(11) 0.0000(9) 0.0092(9) -0.0017(10) C16 0.0530(13) 0.0356(13) 0.0359(12) -0.0074(10) 0.0118(10) -0.0020(10) C17 0.0554(14) 0.0368(13) 0.0372(12) -0.0092(10) 0.0080(10) -0.0138(11) C18 0.0425(12) 0.0482(15) 0.0341(12) -0.0030(11) 0.0041(9) -0.0077(11) C19 0.0398(11) 0.0356(13) 0.0271(10) 0.0004(9) 0.0056(9) -0.0034(10) C20 0.0407(11) 0.0370(13) 0.0452(13) -0.0056(10) 0.0118(10) 0.0009(10) C21 0.0531(14) 0.0571(16) 0.0679(16) -0.0133(13) 0.0205(12) 0.0084(12) C22 0.0445(13) 0.0689(18) 0.0565(15) 0.0060(14) -0.0020(11) 0.0035(12) C23 0.0373(11) 0.0377(13) 0.0459(13) -0.0008(11) -0.0037(10) 0.0008(10) C24 0.0775(17) 0.0684(19) 0.0776(19) -0.0024(16) 0.0362(15) 0.0176(15) C25 0.0721(16) 0.0683(18) 0.0640(17) 0.0040(15) -0.0163(14) 0.0138(14) N1 0.0373(9) 0.0370(10) 0.0263(9) -0.0029(8) 0.0035(7) 0.0009(8) N2 0.0365(9) 0.0323(10) 0.0284(9) -0.0023(8) 0.0049(7) -0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.213(2) . ? C1 N2 1.221(2) . ? C2 C7 1.400(3) . ? C2 C3 1.408(3) . ? C2 N1 1.415(2) . ? C3 C4 1.392(3) . ? C3 C8 1.510(3) . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.376(3) . ? C5 H5 0.9500 . ? C6 C7 1.390(3) . ? C6 H6 0.9500 . ? C7 C11 1.519(3) . ? C8 C10 1.525(3) . ? C8 C9 1.527(3) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.520(3) . ? C11 C13 1.522(3) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.401(3) . ? C14 C19 1.405(3) . ? C14 N2 1.425(2) . ? C15 C16 1.398(3) . ? C15 C20 1.519(3) . ? C16 C17 1.375(3) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 C23 1.522(3) . ? C20 C22 1.527(3) . ? C20 C21 1.530(3) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.520(3) . ? C23 C24 1.526(3) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 169.3(2) . . ? C7 C2 C3 122.68(17) . . ? C7 C2 N1 115.66(17) . . ? C3 C2 N1 121.64(18) . . ? C4 C3 C2 116.71(19) . . ? C4 C3 C8 121.55(17) . . ? C2 C3 C8 121.72(17) . . ? C5 C4 C3 121.51(19) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 120.46(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.9(2) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 117.68(18) . . ? C6 C7 C11 121.46(19) . . ? C2 C7 C11 120.82(17) . . ? C3 C8 C10 110.69(17) . . ? C3 C8 C9 114.03(17) . . ? C10 C8 C9 110.17(18) . . ? C3 C8 H8 107.2 . . ? C10 C8 H8 107.2 . . ? C9 C8 H8 107.2 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 C12 109.91(18) . . ? C7 C11 C13 113.93(17) . . ? C12 C11 C13 110.32(18) . . ? C7 C11 H11 107.5 . . ? C12 C11 H11 107.5 . . ? C13 C11 H11 107.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 121.97(17) . . ? C15 C14 N2 117.05(16) . . ? C19 C14 N2 120.86(17) . . ? C16 C15 C14 117.53(18) . . ? C16 C15 C20 120.77(18) . . ? C14 C15 C20 121.70(17) . . ? C17 C16 C15 121.1(2) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 120.06(19) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 121.40(18) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C14 117.80(18) . . ? C18 C19 C23 120.18(17) . . ? C14 C19 C23 122.02(17) . . ? C15 C20 C22 111.08(17) . . ? C15 C20 C21 111.86(17) . . ? C22 C20 C21 111.02(18) . . ? C15 C20 H20 107.6 . . ? C22 C20 H20 107.6 . . ? C21 C20 H20 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C19 112.54(19) . . ? C25 C23 C24 111.2(2) . . ? C19 C23 C24 111.66(18) . . ? C25 C23 H23 107.0 . . ? C19 C23 H23 107.0 . . ? C24 C23 H23 107.0 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C1 N1 C2 138.73(17) . . ? C1 N2 C14 131.51(17) . . ? 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 C7 C2 C3 C4 0.4(3) . . . . ? N1 C2 C3 C4 178.53(18) . . . . ? C7 C2 C3 C8 -177.92(17) . . . . ? N1 C2 C3 C8 0.2(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C8 C3 C4 C5 178.20(18) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C2 0.0(3) . . . . ? C5 C6 C7 C11 177.82(19) . . . . ? C3 C2 C7 C6 -0.3(3) . . . . ? N1 C2 C7 C6 -178.56(17) . . . . ? C3 C2 C7 C11 -178.18(18) . . . . ? N1 C2 C7 C11 3.6(3) . . . . ? C4 C3 C8 C10 -99.0(2) . . . . ? C2 C3 C8 C10 79.2(2) . . . . ? C4 C3 C8 C9 25.9(3) . . . . ? C2 C3 C8 C9 -155.91(19) . . . . ? C6 C7 C11 C12 -91.1(2) . . . . ? C2 C7 C11 C12 86.6(2) . . . . ? C6 C7 C11 C13 33.2(3) . . . . ? C2 C7 C11 C13 -149.0(2) . . . . ? C19 C14 C15 C16 -3.7(3) . . . . ? N2 C14 C15 C16 -179.63(16) . . . . ? C19 C14 C15 C20 177.28(18) . . . . ? N2 C14 C15 C20 1.3(3) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? C20 C15 C16 C17 -179.75(18) . . . . ? C15 C16 C17 C18 1.3(3) . . . . ? C16 C17 C18 C19 -1.5(3) . . . . ? C17 C18 C19 C14 -0.9(3) . . . . ? C17 C18 C19 C23 178.12(19) . . . . ? C15 C14 C19 C18 3.6(3) . . . . ? N2 C14 C19 C18 179.35(17) . . . . ? C15 C14 C19 C23 -175.48(18) . . . . ? N2 C14 C19 C23 0.3(3) . . . . ? C16 C15 C20 C22 -78.1(2) . . . . ? C14 C15 C20 C22 100.9(2) . . . . ? C16 C15 C20 C21 46.5(3) . . . . ? C14 C15 C20 C21 -134.4(2) . . . . ? C18 C19 C23 C25 -50.3(3) . . . . ? C14 C19 C23 C25 128.7(2) . . . . ? C18 C19 C23 C24 75.5(3) . . . . ? C14 C19 C23 C24 -105.4(2) . . . . ? N2 C1 N1 C2 -136.1(9) . . . . ? C7 C2 N1 C1 -170.7(2) . . . . ? C3 C2 N1 C1 11.0(4) . . . . ? N1 C1 N2 C14 -130.8(9) . . . . ? C15 C14 N2 C1 -130.7(2) . . . . ? C19 C14 N2 C1 53.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.181 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.042 # Attachment 'compound12.cif' data_nhnh091 _database_code_depnum_ccdc_archive 'CCDC 645036' _chemical_formula_moiety 'C19 H22 N2' _chemical_formula_sum 'C19 H22 N2' _chemical_formula_weight 278.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.400(5) _cell_length_b 8.612(5) _cell_length_c 11.692(5) _cell_angle_alpha 76.709(5) _cell_angle_beta 75.502(5) _cell_angle_gamma 82.349(5) _cell_volume 794.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5357 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_reflns_number 5357 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3594 _reflns_number_gt 2699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0758P)^2^+0.1579P] 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_number_reflns 3594 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 C1 C -0.11897(17) 0.56646(16) 0.28457(12) 0.0280(3) Uani 1 1 d . . . C2 C -0.36357(16) 0.41668(15) 0.36866(11) 0.0245(3) Uani 1 1 d . . . C3 C -0.48375(17) 0.51419(15) 0.31479(11) 0.0259(3) Uani 1 1 d . . . C4 C -0.64280(17) 0.46557(16) 0.34680(12) 0.0271(3) Uani 1 1 d . . . H4 H -0.7252 0.5307 0.3109 0.033 Uiso 1 1 calc R . . C5 C -0.68597(17) 0.32495(16) 0.42952(12) 0.0260(3) Uani 1 1 d . . . C6 C -0.56357(17) 0.23197(15) 0.48161(11) 0.0255(3) Uani 1 1 d . . . H6 H -0.5911 0.1360 0.5388 0.031 Uiso 1 1 calc R . . C7 C -0.40253(16) 0.27497(15) 0.45271(11) 0.0245(3) Uani 1 1 d . . . C8 C -0.4438(2) 0.66826(16) 0.22610(13) 0.0339(3) Uani 1 1 d . . . H8A H -0.5401 0.7138 0.1930 0.051 Uiso 1 1 calc R . . H8B H -0.3506 0.6473 0.1604 0.051 Uiso 1 1 calc R . . H8C H -0.4147 0.7440 0.2671 0.051 Uiso 1 1 calc R . . C9 C -0.85829(18) 0.27442(18) 0.46006(14) 0.0337(3) Uani 1 1 d . . . H9A H -0.9371 0.3690 0.4624 0.051 Uiso 1 1 calc R . . H9B H -0.8789 0.2016 0.5391 0.051 Uiso 1 1 calc R . . H9C H -0.8715 0.2196 0.3986 0.051 Uiso 1 1 calc R . . C10 C -0.27325(18) 0.17373(17) 0.51186(14) 0.0335(3) Uani 1 1 d . . . H10A H -0.3222 0.0803 0.5684 0.050 Uiso 1 1 calc R . . H10B H -0.2306 0.2369 0.5558 0.050 Uiso 1 1 calc R . . H10C H -0.1828 0.1380 0.4500 0.050 Uiso 1 1 calc R . . C11 C 0.09361(16) 0.72090(15) 0.13916(11) 0.0252(3) Uani 1 1 d . . . C12 C 0.13180(17) 0.88084(15) 0.11002(12) 0.0275(3) Uani 1 1 d . . . C13 C 0.25517(18) 0.92902(16) 0.00834(12) 0.0298(3) Uani 1 1 d . . . H13 H 0.2808 1.0376 -0.0127 0.036 Uiso 1 1 calc R . . C14 C 0.34216(18) 0.82418(16) -0.06350(12) 0.0298(3) Uani 1 1 d . . . C15 C 0.30321(19) 0.66582(16) -0.03093(12) 0.0306(3) Uani 1 1 d . . . H15 H 0.3628 0.5924 -0.0788 0.037 Uiso 1 1 calc R . . C16 C 0.18030(18) 0.61105(15) 0.06913(12) 0.0282(3) Uani 1 1 d . . . C17 C 0.0413(2) 0.99723(17) 0.18764(14) 0.0384(4) Uani 1 1 d . . . H17A H 0.0671 1.1064 0.1458 0.058 Uiso 1 1 calc R . . H17B H 0.0758 0.9719 0.2644 0.058 Uiso 1 1 calc R . . H17C H -0.0777 0.9890 0.2032 0.058 Uiso 1 1 calc R . . C18 C 0.4730(2) 0.87979(19) -0.17493(14) 0.0423(4) Uani 1 1 d . . . H18A H 0.4204 0.9380 -0.2401 0.063 Uiso 1 1 calc R . . H18B H 0.5419 0.7869 -0.1999 0.063 Uiso 1 1 calc R . . H18C H 0.5417 0.9507 -0.1573 0.063 Uiso 1 1 calc R . . C19 C 0.1444(2) 0.43728(16) 0.10260(13) 0.0379(4) Uani 1 1 d . . . H19A H 0.1560 0.3924 0.1853 0.057 Uiso 1 1 calc R . . H19B H 0.2223 0.3780 0.0471 0.057 Uiso 1 1 calc R . . H19C H 0.0315 0.4285 0.0971 0.057 Uiso 1 1 calc R . . N1 N -0.19945(15) 0.45644(14) 0.34338(11) 0.0308(3) Uani 1 1 d . . . N2 N -0.02805(15) 0.67486(14) 0.24498(11) 0.0319(3) 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 C1 0.0269(7) 0.0283(7) 0.0278(7) -0.0041(5) -0.0050(5) -0.0035(6) C2 0.0232(7) 0.0250(7) 0.0249(6) -0.0057(5) -0.0027(5) -0.0052(5) C3 0.0322(8) 0.0228(7) 0.0235(6) -0.0052(5) -0.0067(5) -0.0038(6) C4 0.0282(7) 0.0267(7) 0.0281(7) -0.0052(5) -0.0109(5) 0.0001(6) C5 0.0247(7) 0.0282(7) 0.0262(7) -0.0083(5) -0.0040(5) -0.0042(5) C6 0.0273(7) 0.0241(7) 0.0241(6) -0.0027(5) -0.0043(5) -0.0051(5) C7 0.0238(7) 0.0230(6) 0.0265(7) -0.0045(5) -0.0055(5) -0.0030(5) C8 0.0414(9) 0.0274(7) 0.0320(7) 0.0008(6) -0.0111(6) -0.0063(6) C9 0.0262(8) 0.0377(8) 0.0371(8) -0.0046(6) -0.0082(6) -0.0060(6) C10 0.0274(8) 0.0279(7) 0.0419(8) 0.0022(6) -0.0097(6) -0.0032(6) C11 0.0254(7) 0.0257(7) 0.0238(6) -0.0004(5) -0.0057(5) -0.0074(5) C12 0.0302(8) 0.0229(7) 0.0286(7) -0.0029(5) -0.0066(6) -0.0037(6) C13 0.0375(8) 0.0192(6) 0.0309(7) -0.0001(5) -0.0062(6) -0.0075(6) C14 0.0334(8) 0.0275(7) 0.0261(7) -0.0015(5) -0.0041(6) -0.0063(6) C15 0.0381(8) 0.0257(7) 0.0274(7) -0.0070(5) -0.0047(6) -0.0030(6) C16 0.0353(8) 0.0235(7) 0.0265(7) -0.0021(5) -0.0087(6) -0.0074(6) C17 0.0426(9) 0.0285(8) 0.0398(8) -0.0085(6) 0.0011(7) -0.0051(7) C18 0.0500(10) 0.0329(8) 0.0359(8) -0.0039(6) 0.0052(7) -0.0102(7) C19 0.0555(10) 0.0251(7) 0.0321(8) -0.0056(6) -0.0040(7) -0.0111(7) N1 0.0266(7) 0.0293(6) 0.0335(6) 0.0005(5) -0.0048(5) -0.0078(5) N2 0.0325(7) 0.0298(6) 0.0316(6) -0.0044(5) -0.0015(5) -0.0109(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.2107(18) . ? C1 N2 1.2179(18) . ? C2 C7 1.3986(19) . ? C2 C3 1.4037(19) . ? C2 N1 1.4072(19) . ? C3 C4 1.388(2) . ? C3 C8 1.5033(19) . ? C4 C5 1.3915(19) . ? C4 H4 0.9500 . ? C5 C6 1.3926(19) . ? C5 C9 1.500(2) . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C10 1.5049(19) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.4012(19) . ? C11 C16 1.404(2) . ? C11 N2 1.4077(18) . ? C12 C13 1.389(2) . ? C12 C17 1.509(2) . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? C14 C15 1.389(2) . ? C14 C18 1.507(2) . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 C19 1.509(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 167.82(15) . . ? C7 C2 C3 121.17(12) . . ? C7 C2 N1 116.39(12) . . ? C3 C2 N1 122.42(12) . . ? C4 C3 C2 118.08(12) . . ? C4 C3 C8 120.34(12) . . ? C2 C3 C8 121.57(13) . . ? C3 C4 C5 122.38(12) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 117.84(13) . . ? C4 C5 C9 120.92(12) . . ? C6 C5 C9 121.23(12) . . ? C7 C6 C5 122.13(12) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C2 118.40(12) . . ? C6 C7 C10 121.06(12) . . ? C2 C7 C10 120.53(12) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 120.91(13) . . ? C12 C11 N2 116.84(12) . . ? C16 C11 N2 122.15(12) . . ? C13 C12 C11 118.33(13) . . ? C13 C12 C17 121.02(12) . . ? C11 C12 C17 120.65(13) . . ? C14 C13 C12 122.28(12) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 117.94(13) . . ? C13 C14 C18 121.40(13) . . ? C15 C14 C18 120.65(13) . . ? C16 C15 C14 122.35(13) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C11 118.17(12) . . ? C15 C16 C19 120.57(13) . . ? C11 C16 C19 121.25(13) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N1 C2 137.62(13) . . ? C1 N2 C11 135.75(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C3 C4 -0.35(19) . . . . ? N1 C2 C3 C4 -179.19(12) . . . . ? C7 C2 C3 C8 178.84(12) . . . . ? N1 C2 C3 C8 0.0(2) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C8 C3 C4 C5 -179.23(12) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C3 C4 C5 C9 -178.73(12) . . . . ? C4 C5 C6 C7 -0.50(19) . . . . ? C9 C5 C6 C7 178.66(12) . . . . ? C5 C6 C7 C2 0.15(19) . . . . ? C5 C6 C7 C10 178.98(13) . . . . ? C3 C2 C7 C6 0.29(19) . . . . ? N1 C2 C7 C6 179.20(11) . . . . ? C3 C2 C7 C10 -178.55(12) . . . . ? N1 C2 C7 C10 0.36(19) . . . . ? C16 C11 C12 C13 1.5(2) . . . . ? N2 C11 C12 C13 177.91(12) . . . . ? C16 C11 C12 C17 -178.30(13) . . . . ? N2 C11 C12 C17 -1.87(19) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C17 C12 C13 C14 178.93(13) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C12 C13 C14 C18 178.66(14) . . . . ? C13 C14 C15 C16 0.8(2) . . . . ? C18 C14 C15 C16 -178.15(14) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C14 C15 C16 C19 -178.78(13) . . . . ? C12 C11 C16 C15 -1.0(2) . . . . ? N2 C11 C16 C15 -177.24(12) . . . . ? C12 C11 C16 C19 177.63(13) . . . . ? N2 C11 C16 C19 1.4(2) . . . . ? N2 C1 N1 C2 131.6(7) . . . . ? C7 C2 N1 C1 -175.19(16) . . . . ? C3 C2 N1 C1 3.7(3) . . . . ? N1 C1 N2 C11 133.0(7) . . . . ? C12 C11 N2 C1 159.41(16) . . . . ? C16 C11 N2 C1 -24.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.210 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.052 # Attachment 'compund15.cif' data_mfnh078 _database_code_depnum_ccdc_archive 'CCDC 645037' #3. data _chemical_formula_moiety 'C37 H44 B Cl2 N3' _chemical_formula_sum 'C37 H44 B Cl2 N3' _chemical_formula_weight 612.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Pc _symmetry_space_group_name_Hall P-2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 12.258(5) _cell_length_b 10.481(4) _cell_length_c 16.149(5) _cell_angle_alpha 90 _cell_angle_beta 124.90(2) _cell_angle_gamma 90 _cell_volume 1701.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 13089 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_reflns_number 6945 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.1304 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6936 _reflns_number_gt 4041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.0000P] 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 0.54(8) _refine_ls_number_reflns 6936 _refine_ls_number_parameters 389 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1455 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1812 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.087 _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 C1 C -0.4983(5) -0.2251(4) -0.5549(4) 0.0249(11) Uani 1 1 d . . . C2 C -0.7425(4) -0.2706(4) -0.6656(4) 0.0262(11) Uani 1 1 d . . . C3 C -0.8139(5) -0.3545(4) -0.7484(4) 0.0283(11) Uani 1 1 d . . . C4 C -0.9280(5) -0.4108(5) -0.7656(4) 0.0378(13) Uani 1 1 d . . . H4 H -0.9778 -0.4678 -0.8209 0.045 Uiso 1 1 calc R . . C5 C -0.9707(5) -0.3863(5) -0.7048(4) 0.0394(13) Uani 1 1 d . . . H5 H -1.0463 -0.4292 -0.7158 0.047 Uiso 1 1 calc R . . C6 C -0.9021(5) -0.2982(5) -0.6272(4) 0.0352(12) Uani 1 1 d . . . H6 H -0.9340 -0.2787 -0.5872 0.042 Uiso 1 1 calc R . . C7 C -0.7880(5) -0.2379(4) -0.6062(4) 0.0283(11) Uani 1 1 d . . . C8 C -0.7770(5) -0.3762(5) -0.8227(4) 0.0333(12) Uani 1 1 d . . . H8 H -0.6816 -0.3514 -0.7884 0.040 Uiso 1 1 calc R . . C9 C -0.8620(6) -0.2876(6) -0.9149(5) 0.0486(15) Uani 1 1 d . . . H9A H -0.8388 -0.3015 -0.9630 0.073 Uiso 1 1 calc R . . H9B H -0.8445 -0.1985 -0.8925 0.073 Uiso 1 1 calc R . . H9C H -0.9565 -0.3066 -0.9475 0.073 Uiso 1 1 calc R . . C10 C -0.7915(6) -0.5140(5) -0.8567(5) 0.0486(16) Uani 1 1 d . . . H10A H -0.7662 -0.5214 -0.9041 0.073 Uiso 1 1 calc R . . H10B H -0.8842 -0.5411 -0.8901 0.073 Uiso 1 1 calc R . . H10C H -0.7336 -0.5685 -0.7979 0.073 Uiso 1 1 calc R . . C11 C -0.7283(5) -0.1342(4) -0.5264(4) 0.0319(12) Uani 1 1 d . . . H11 H -0.6459 -0.1022 -0.5184 0.038 Uiso 1 1 calc R . . C12 C -0.6896(6) -0.1841(5) -0.4240(4) 0.0404(13) Uani 1 1 d . . . H12A H -0.6513 -0.1145 -0.3746 0.061 Uiso 1 1 calc R . . H12B H -0.6238 -0.2525 -0.4015 0.061 Uiso 1 1 calc R . . H12C H -0.7687 -0.2174 -0.4303 0.061 Uiso 1 1 calc R . . C13 C -0.8248(6) -0.0220(5) -0.5594(5) 0.0455(15) Uani 1 1 d . . . H13A H -0.7845 0.0438 -0.5068 0.068 Uiso 1 1 calc R . . H13B H -0.9076 -0.0518 -0.5699 0.068 Uiso 1 1 calc R . . H13C H -0.8440 0.0137 -0.6225 0.068 Uiso 1 1 calc R . . C14 C -0.2949(5) -0.1148(4) -0.5191(4) 0.0267(11) Uani 1 1 d . . . C15 C -0.2212(5) -0.2137(5) -0.5229(4) 0.0325(12) Uani 1 1 d . . . C16 C -0.0845(5) -0.1998(6) -0.4686(4) 0.0422(14) Uani 1 1 d . . . H16 H -0.0325 -0.2666 -0.4692 0.051 Uiso 1 1 calc R . . C17 C -0.0220(5) -0.0901(6) -0.4132(5) 0.0479(15) Uani 1 1 d . . . H17 H 0.0722 -0.0840 -0.3736 0.057 Uiso 1 1 calc R . . C18 C -0.0964(6) 0.0099(6) -0.4154(5) 0.0488(16) Uani 1 1 d . . . H18 H -0.0528 0.0862 -0.3799 0.059 Uiso 1 1 calc R . . C19 C -0.2341(5) 0.0017(5) -0.4686(4) 0.0347(13) Uani 1 1 d . . . C20 C -0.2850(5) -0.3297(4) -0.5925(4) 0.0312(12) Uani 1 1 d . . . H20 H -0.3835 -0.3245 -0.6274 0.037 Uiso 1 1 calc R . . C21 C -0.2375(6) -0.4572(5) -0.5384(5) 0.0507(15) Uani 1 1 d . . . H21A H -0.2830 -0.5265 -0.5874 0.076 Uiso 1 1 calc R . . H21B H -0.2576 -0.4625 -0.4878 0.076 Uiso 1 1 calc R . . H21C H -0.1413 -0.4649 -0.5049 0.076 Uiso 1 1 calc R . . C22 C -0.2555(6) -0.3257(6) -0.6732(4) 0.0456(14) Uani 1 1 d . . . H22A H -0.2868 -0.2445 -0.7097 0.068 Uiso 1 1 calc R . . H22B H -0.3016 -0.3963 -0.7207 0.068 Uiso 1 1 calc R . . H22C H -0.1595 -0.3336 -0.6405 0.068 Uiso 1 1 calc R . . C23 C -0.3164(5) 0.1172(5) -0.4804(4) 0.0398(14) Uani 1 1 d . . . H23 H -0.4027 0.0859 -0.4947 0.048 Uiso 1 1 calc R . . C24 C -0.3471(6) 0.1945(5) -0.5712(5) 0.0506(16) Uani 1 1 d . . . H24A H -0.4009 0.2690 -0.5796 0.076 Uiso 1 1 calc R . . H24B H -0.3966 0.1413 -0.6320 0.076 Uiso 1 1 calc R . . H24C H -0.2638 0.2228 -0.5605 0.076 Uiso 1 1 calc R . . C25 C -0.2512(7) 0.2023(6) -0.3873(6) 0.0632(19) Uani 1 1 d . . . H25A H -0.3101 0.2742 -0.4002 0.095 Uiso 1 1 calc R . . H25B H -0.1665 0.2345 -0.3719 0.095 Uiso 1 1 calc R . . H25C H -0.2352 0.1528 -0.3298 0.095 Uiso 1 1 calc R . . C26 C -0.3404(5) -0.2558(4) -0.3743(4) 0.0300(12) Uani 1 1 d . . . C27 C -0.2278(6) -0.3305(6) -0.3142(4) 0.0469(15) Uani 1 1 d . . . H27 H -0.2196 -0.4105 -0.3379 0.056 Uiso 1 1 calc R . . C28 C -0.1285(6) -0.2868(6) -0.2200(5) 0.0540(16) Uani 1 1 d . . . H28 H -0.0508 -0.3370 -0.1787 0.065 Uiso 1 1 calc R . . C29 C -0.1393(6) -0.1718(6) -0.1843(5) 0.0501(15) Uani 1 1 d . . . H29 H -0.0692 -0.1423 -0.1194 0.060 Uiso 1 1 calc R . . C30 C -0.2520(6) -0.1005(5) -0.2432(4) 0.0441(14) Uani 1 1 d . . . H30 H -0.2611 -0.0224 -0.2179 0.053 Uiso 1 1 calc R . . C31 C -0.3524(5) -0.1405(5) -0.3387(4) 0.0348(12) Uani 1 1 d . . . H31 H -0.4294 -0.0892 -0.3797 0.042 Uiso 1 1 calc R . . C32 C -0.5019(5) -0.4265(5) -0.4816(4) 0.0341(13) Uani 1 1 d . . . C33 C -0.5499(5) -0.4996(4) -0.5675(4) 0.0352(12) Uani 1 1 d . . . H33 H -0.5466 -0.4680 -0.6212 0.042 Uiso 1 1 calc R . . C34 C -0.6032(5) -0.6202(5) -0.5743(5) 0.0452(15) Uani 1 1 d . . . H34 H -0.6375 -0.6701 -0.6335 0.054 Uiso 1 1 calc R . . C35 C -0.6065(6) -0.6676(5) -0.4962(5) 0.0510(17) Uani 1 1 d . . . H35 H -0.6434 -0.7494 -0.5015 0.061 Uiso 1 1 calc R . . C36 C -0.5557(6) -0.5953(5) -0.4105(5) 0.0466(15) Uani 1 1 d . . . H36 H -0.5555 -0.6288 -0.3557 0.056 Uiso 1 1 calc R . . C37 C -0.5050(5) -0.4745(5) -0.4029(4) 0.0397(13) Uani 1 1 d . . . H37 H -0.4724 -0.4247 -0.3440 0.048 Uiso 1 1 calc R . . B B -0.5686(5) -0.1033(5) -0.6728(4) 0.0281(13) Uani 1 1 d . . . N1 N -0.6183(3) -0.2225(3) -0.6433(3) 0.0222(8) Uani 1 1 d . . . N2 N -0.4358(3) -0.1263(3) -0.5660(3) 0.0230(8) Uani 1 1 d . . . N3 N -0.4474(4) -0.3015(3) -0.4731(3) 0.0271(9) Uani 1 1 d . . . Cl1 Cl -0.54692(11) -0.12150(10) -0.77539(9) 0.0348(3) Uani 1 1 d . . . Cl2 Cl -0.66239(12) 0.04179(10) -0.68893(10) 0.0365(3) 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 C1 0.034(3) 0.018(2) 0.028(3) -0.002(2) 0.021(3) 0.000(2) C2 0.022(2) 0.025(2) 0.028(3) 0.001(2) 0.012(2) 0.001(2) C3 0.029(3) 0.028(3) 0.027(3) -0.003(2) 0.016(2) 0.001(2) C4 0.031(3) 0.042(3) 0.039(3) -0.012(2) 0.019(3) -0.009(2) C5 0.032(3) 0.044(3) 0.044(4) -0.008(3) 0.023(3) -0.011(2) C6 0.031(3) 0.043(3) 0.033(3) -0.005(2) 0.020(3) -0.003(2) C7 0.029(3) 0.028(2) 0.029(3) -0.002(2) 0.017(2) 0.001(2) C8 0.033(3) 0.038(3) 0.030(3) -0.010(2) 0.019(3) -0.003(2) C9 0.044(3) 0.062(4) 0.036(4) -0.001(3) 0.021(3) 0.003(3) C10 0.050(3) 0.045(3) 0.062(4) -0.029(3) 0.039(3) -0.016(3) C11 0.033(3) 0.031(3) 0.041(3) -0.006(2) 0.027(3) -0.005(2) C12 0.049(3) 0.040(3) 0.039(4) -0.008(3) 0.030(3) -0.004(3) C13 0.057(4) 0.034(3) 0.056(4) 0.000(3) 0.039(4) 0.007(3) C14 0.026(3) 0.034(3) 0.024(3) 0.002(2) 0.017(2) 0.000(2) C15 0.030(3) 0.035(3) 0.034(3) 0.007(2) 0.019(3) 0.002(2) C16 0.025(3) 0.056(4) 0.041(4) 0.001(3) 0.016(3) 0.003(2) C17 0.025(3) 0.060(4) 0.051(4) -0.010(3) 0.017(3) -0.011(3) C18 0.041(3) 0.059(4) 0.047(4) -0.023(3) 0.026(3) -0.019(3) C19 0.037(3) 0.040(3) 0.036(3) -0.011(2) 0.026(3) -0.010(2) C20 0.026(3) 0.033(3) 0.038(3) 0.001(2) 0.020(3) 0.002(2) C21 0.050(3) 0.034(3) 0.068(4) 0.007(3) 0.034(3) 0.012(3) C22 0.044(3) 0.053(3) 0.047(4) -0.006(3) 0.030(3) -0.001(3) C23 0.046(3) 0.035(3) 0.055(4) -0.016(3) 0.039(3) -0.015(2) C24 0.067(4) 0.035(3) 0.076(5) 0.004(3) 0.057(4) 0.002(3) C25 0.065(4) 0.059(4) 0.080(5) -0.039(4) 0.050(4) -0.028(3) C26 0.029(3) 0.035(3) 0.020(3) 0.008(2) 0.011(2) -0.001(2) C27 0.046(4) 0.048(3) 0.033(4) 0.004(3) 0.015(3) 0.011(3) C28 0.042(3) 0.064(4) 0.034(4) 0.004(3) 0.009(3) 0.010(3) C29 0.044(4) 0.061(4) 0.026(3) 0.003(3) 0.008(3) -0.010(3) C30 0.056(4) 0.046(3) 0.031(3) -0.009(3) 0.025(3) -0.009(3) C31 0.032(3) 0.037(3) 0.034(3) 0.003(2) 0.018(3) -0.001(2) C32 0.030(3) 0.029(3) 0.046(4) 0.010(2) 0.023(3) 0.008(2) C33 0.039(3) 0.025(3) 0.041(4) 0.001(2) 0.022(3) 0.000(2) C34 0.043(3) 0.034(3) 0.053(4) -0.003(3) 0.024(3) 0.001(2) C35 0.048(4) 0.029(3) 0.083(5) 0.011(3) 0.042(4) -0.003(3) C36 0.049(3) 0.041(3) 0.062(5) 0.020(3) 0.039(4) 0.002(3) C37 0.048(3) 0.041(3) 0.043(4) 0.011(3) 0.033(3) 0.003(3) B 0.028(3) 0.025(3) 0.032(3) 0.002(2) 0.018(3) 0.003(2) N1 0.021(2) 0.0237(19) 0.019(2) -0.0011(17) 0.0102(19) -0.0001(16) N2 0.025(2) 0.0211(18) 0.025(2) -0.0008(17) 0.0151(19) -0.0016(16) N3 0.028(2) 0.028(2) 0.026(3) 0.0029(18) 0.016(2) -0.0006(17) Cl1 0.0458(7) 0.0326(6) 0.0318(7) 0.0013(6) 0.0255(7) 0.0011(6) Cl2 0.0414(7) 0.0283(6) 0.0405(8) 0.0031(6) 0.0238(6) 0.0063(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 C1 N1 1.341(6) . ? C1 N3 1.352(6) . ? C1 N2 1.360(6) . ? C2 C7 1.401(7) . ? C2 C3 1.409(7) . ? C2 N1 1.440(6) . ? C3 C4 1.393(7) . ? C3 C8 1.521(7) . ? C4 C5 1.376(7) . ? C4 H4 0.9500 . ? C5 C6 1.387(7) . ? C5 H5 0.9500 . ? C6 C7 1.388(7) . ? C6 H6 0.9500 . ? C7 C11 1.516(7) . ? C8 C10 1.519(7) . ? C8 C9 1.546(8) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.528(7) . ? C11 C13 1.530(7) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.400(7) . ? C14 C19 1.419(7) . ? C14 N2 1.441(6) . ? C15 C16 1.385(7) . ? C15 C20 1.531(7) . ? C16 C17 1.387(8) . ? C16 H16 0.9500 . ? C17 C18 1.376(8) . ? C17 H17 0.9500 . ? C18 C19 1.391(7) . ? C18 H18 0.9500 . ? C19 C23 1.517(7) . ? C20 C21 1.518(7) . ? C20 C22 1.539(7) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.522(8) . ? C23 C25 1.523(8) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C31 1.382(7) . ? C26 C27 1.388(7) . ? C26 N3 1.449(6) . ? C27 C28 1.374(8) . ? C27 H27 0.9500 . ? C28 C29 1.375(8) . ? C28 H28 0.9500 . ? C29 C30 1.367(8) . ? C29 H29 0.9500 . ? C30 C31 1.377(8) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C37 1.387(7) . ? C32 C33 1.387(7) . ? C32 N3 1.442(6) . ? C33 C34 1.399(7) . ? C33 H33 0.9500 . ? C34 C35 1.376(9) . ? C34 H34 0.9500 . ? C35 C36 1.376(9) . ? C35 H35 0.9500 . ? C36 C37 1.385(7) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? B N2 1.571(7) . ? B N1 1.579(7) . ? B Cl1 1.832(6) . ? B Cl2 1.832(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 N1 C1 N3 131.6(4) . . ? N1 C1 N2 101.6(4) . . ? N3 C1 N2 126.8(4) . . ? C7 C2 C3 121.9(4) . . ? C7 C2 N1 121.4(4) . . ? C3 C2 N1 116.7(4) . . ? C4 C3 C2 117.5(4) . . ? C4 C3 C8 119.8(4) . . ? C2 C3 C8 122.5(4) . . ? C5 C4 C3 121.8(5) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.2(5) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 122.0(5) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C6 C7 C2 117.5(4) . . ? C6 C7 C11 117.6(4) . . ? C2 C7 C11 124.8(4) . . ? C10 C8 C3 113.7(4) . . ? C10 C8 C9 110.4(4) . . ? C3 C8 C9 109.2(4) . . ? C10 C8 H8 107.8 . . ? C3 C8 H8 107.8 . . ? C9 C8 H8 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 C12 112.0(4) . . ? C7 C11 C13 110.7(4) . . ? C12 C11 C13 109.9(4) . . ? C7 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C13 C11 H11 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 121.5(4) . . ? C15 C14 N2 121.6(4) . . ? C19 C14 N2 116.8(4) . . ? C16 C15 C14 118.1(5) . . ? C16 C15 C20 118.2(5) . . ? C14 C15 C20 123.3(4) . . ? C15 C16 C17 121.1(5) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 120.1(5) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 121.3(5) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C14 117.4(4) . . ? C18 C19 C23 120.9(4) . . ? C14 C19 C23 121.4(4) . . ? C21 C20 C15 114.2(5) . . ? C21 C20 C22 108.3(4) . . ? C15 C20 C22 109.3(4) . . ? C21 C20 H20 108.3 . . ? C15 C20 H20 108.3 . . ? C22 C20 H20 108.3 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 C24 109.0(4) . . ? C19 C23 C25 114.0(5) . . ? C24 C23 C25 109.9(5) . . ? C19 C23 H23 107.9 . . ? C24 C23 H23 107.9 . . ? C25 C23 H23 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C31 C26 C27 120.2(5) . . ? C31 C26 N3 120.2(4) . . ? C27 C26 N3 119.6(5) . . ? C28 C27 C26 118.8(5) . . ? C28 C27 H27 120.6 . . ? C26 C27 H27 120.6 . . ? C27 C28 C29 121.3(5) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C30 C29 C28 119.3(5) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? C29 C30 C31 120.9(5) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C30 C31 C26 119.5(5) . . ? C30 C31 H31 120.3 . . ? C26 C31 H31 120.3 . . ? C37 C32 C33 119.8(5) . . ? C37 C32 N3 119.8(5) . . ? C33 C32 N3 120.3(5) . . ? C32 C33 C34 119.3(5) . . ? C32 C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? C35 C34 C33 120.8(6) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C36 C35 C34 119.4(5) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? C35 C36 C37 120.9(5) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C36 C37 C32 119.8(5) . . ? C36 C37 H37 120.1 . . ? C32 C37 H37 120.1 . . ? N2 B N1 83.3(3) . . ? N2 B Cl1 112.4(3) . . ? N1 B Cl1 118.1(3) . . ? N2 B Cl2 117.1(3) . . ? N1 B Cl2 112.4(3) . . ? Cl1 B Cl2 111.2(3) . . ? C1 N1 C2 128.1(4) . . ? C1 N1 B 87.7(3) . . ? C2 N1 B 137.5(4) . . ? C1 N2 C14 126.2(4) . . ? C1 N2 B 87.4(3) . . ? C14 N2 B 137.9(4) . . ? C1 N3 C32 121.0(4) . . ? C1 N3 C26 120.0(4) . . ? C32 N3 C26 118.9(4) . . ? 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 C7 C2 C3 C4 -4.1(7) . . . . ? N1 C2 C3 C4 174.4(4) . . . . ? C7 C2 C3 C8 171.0(4) . . . . ? N1 C2 C3 C8 -10.6(6) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C8 C3 C4 C5 -175.1(5) . . . . ? C3 C4 C5 C6 3.2(8) . . . . ? C4 C5 C6 C7 -2.8(8) . . . . ? C5 C6 C7 C2 -1.0(7) . . . . ? C5 C6 C7 C11 174.3(5) . . . . ? C3 C2 C7 C6 4.5(7) . . . . ? N1 C2 C7 C6 -173.8(4) . . . . ? C3 C2 C7 C11 -170.4(4) . . . . ? N1 C2 C7 C11 11.2(7) . . . . ? C4 C3 C8 C10 -44.0(6) . . . . ? C2 C3 C8 C10 141.1(5) . . . . ? C4 C3 C8 C9 79.7(6) . . . . ? C2 C3 C8 C9 -95.2(5) . . . . ? C6 C7 C11 C12 59.3(6) . . . . ? C2 C7 C11 C12 -125.7(5) . . . . ? C6 C7 C11 C13 -63.6(6) . . . . ? C2 C7 C11 C13 111.3(5) . . . . ? C19 C14 C15 C16 5.5(7) . . . . ? N2 C14 C15 C16 -174.4(4) . . . . ? C19 C14 C15 C20 -167.9(4) . . . . ? N2 C14 C15 C20 12.1(7) . . . . ? C14 C15 C16 C17 -1.1(8) . . . . ? C20 C15 C16 C17 172.6(5) . . . . ? C15 C16 C17 C18 -3.2(9) . . . . ? C16 C17 C18 C19 3.2(9) . . . . ? C17 C18 C19 C14 1.1(8) . . . . ? C17 C18 C19 C23 -173.0(6) . . . . ? C15 C14 C19 C18 -5.5(7) . . . . ? N2 C14 C19 C18 174.5(4) . . . . ? C15 C14 C19 C23 168.6(5) . . . . ? N2 C14 C19 C23 -11.5(7) . . . . ? C16 C15 C20 C21 60.8(6) . . . . ? C14 C15 C20 C21 -125.8(5) . . . . ? C16 C15 C20 C22 -60.6(6) . . . . ? C14 C15 C20 C22 112.8(5) . . . . ? C18 C19 C23 C24 85.6(6) . . . . ? C14 C19 C23 C24 -88.2(6) . . . . ? C18 C19 C23 C25 -37.7(7) . . . . ? C14 C19 C23 C25 148.5(5) . . . . ? C31 C26 C27 C28 -1.0(8) . . . . ? N3 C26 C27 C28 -178.8(5) . . . . ? C26 C27 C28 C29 0.6(9) . . . . ? C27 C28 C29 C30 0.9(9) . . . . ? C28 C29 C30 C31 -2.0(8) . . . . ? C29 C30 C31 C26 1.6(8) . . . . ? C27 C26 C31 C30 -0.1(7) . . . . ? N3 C26 C31 C30 177.7(4) . . . . ? C37 C32 C33 C34 1.2(7) . . . . ? N3 C32 C33 C34 -179.6(4) . . . . ? C32 C33 C34 C35 -1.0(8) . . . . ? C33 C34 C35 C36 -0.5(8) . . . . ? C34 C35 C36 C37 1.8(8) . . . . ? C35 C36 C37 C32 -1.6(8) . . . . ? C33 C32 C37 C36 0.1(7) . . . . ? N3 C32 C37 C36 -179.1(4) . . . . ? N3 C1 N1 C2 23.2(7) . . . . ? N2 C1 N1 C2 -156.0(4) . . . . ? N3 C1 N1 B 178.1(5) . . . . ? N2 C1 N1 B -1.1(4) . . . . ? C7 C2 N1 C1 51.0(6) . . . . ? C3 C2 N1 C1 -127.4(5) . . . . ? C7 C2 N1 B -90.2(7) . . . . ? C3 C2 N1 B 91.3(6) . . . . ? N2 B N1 C1 0.9(3) . . . . ? Cl1 B N1 C1 112.8(4) . . . . ? Cl2 B N1 C1 -115.7(4) . . . . ? N2 B N1 C2 151.4(5) . . . . ? Cl1 B N1 C2 -96.7(6) . . . . ? Cl2 B N1 C2 34.8(7) . . . . ? N1 C1 N2 C14 -151.4(4) . . . . ? N3 C1 N2 C14 29.3(7) . . . . ? N1 C1 N2 B 1.1(4) . . . . ? N3 C1 N2 B -178.2(5) . . . . ? C15 C14 N2 C1 50.0(7) . . . . ? C19 C14 N2 C1 -130.0(5) . . . . ? C15 C14 N2 B -86.5(6) . . . . ? C19 C14 N2 B 93.6(6) . . . . ? N1 B N2 C1 -0.9(3) . . . . ? Cl1 B N2 C1 -118.6(3) . . . . ? Cl2 B N2 C1 110.9(4) . . . . ? N1 B N2 C14 145.3(5) . . . . ? Cl1 B N2 C14 27.6(6) . . . . ? Cl2 B N2 C14 -102.9(5) . . . . ? N1 C1 N3 C32 22.8(7) . . . . ? N2 C1 N3 C32 -158.1(4) . . . . ? N1 C1 N3 C26 -154.2(5) . . . . ? N2 C1 N3 C26 24.8(7) . . . . ? C37 C32 N3 C1 -145.5(5) . . . . ? C33 C32 N3 C1 35.2(6) . . . . ? C37 C32 N3 C26 31.5(6) . . . . ? C33 C32 N3 C26 -147.7(4) . . . . ? C31 C26 N3 C1 51.8(6) . . . . ? C27 C26 N3 C1 -130.4(5) . . . . ? C31 C26 N3 C32 -125.3(5) . . . . ? C27 C26 N3 C32 52.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.433 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.185 # Attachment 'compound14.cif' data_mfnh086 _database_code_depnum_ccdc_archive 'CCDC 645038' #3. data _chemical_formula_moiety 'C31 H32 B Cl2 N3' _chemical_formula_sum 'C31 H32 B Cl2 N3' _chemical_formula_weight 528.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.925(5) _cell_length_b 12.612(5) _cell_length_c 16.354(5) _cell_angle_alpha 90 _cell_angle_beta 104.074(5) _cell_angle_gamma 90 _cell_volume 3386(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 13089 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_reflns_number 13089 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7728 _reflns_number_gt 4479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7728 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1426 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 C1 C 0.78777(12) 0.15132(16) 0.17798(12) 0.0245(4) Uani 1 1 d . . . C2 C 0.65278(11) 0.19536(16) 0.20894(12) 0.0269(5) Uani 1 1 d . . . C3 C 0.62349(12) 0.09563(17) 0.22751(12) 0.0296(5) Uani 1 1 d . . . C4 C 0.54183(13) 0.08913(19) 0.22980(14) 0.0374(5) Uani 1 1 d . . . H4 H 0.5211 0.0230 0.2429 0.045 Uiso 1 1 calc R . . C5 C 0.48964(13) 0.1758(2) 0.21362(15) 0.0396(6) Uani 1 1 d . . . C6 C 0.52043(13) 0.2711(2) 0.19546(14) 0.0391(6) Uani 1 1 d . . . H6 H 0.4851 0.3307 0.1839 0.047 Uiso 1 1 calc R . . C7 C 0.60180(13) 0.28373(17) 0.19341(13) 0.0330(5) Uani 1 1 d . . . C8 C 0.67705(13) -0.00137(17) 0.24475(15) 0.0368(5) Uani 1 1 d . . . H8A H 0.6814 -0.0328 0.1912 0.055 Uiso 1 1 calc R . . H8B H 0.6532 -0.0532 0.2765 0.055 Uiso 1 1 calc R . . H8C H 0.7314 0.0188 0.2778 0.055 Uiso 1 1 calc R . . C9 C 0.40041(14) 0.1652(3) 0.2147(2) 0.0608(8) Uani 1 1 d . . . H9A H 0.3768 0.1035 0.1812 0.091 Uiso 1 1 calc R . . H9B H 0.3710 0.2293 0.1908 0.091 Uiso 1 1 calc R . . H9C H 0.3960 0.1561 0.2730 0.091 Uiso 1 1 calc R . . C10 C 0.63358(15) 0.39032(18) 0.17657(18) 0.0477(6) Uani 1 1 d . . . H10A H 0.5878 0.4391 0.1568 0.072 Uiso 1 1 calc R . . H10B H 0.6644 0.3836 0.1333 0.072 Uiso 1 1 calc R . . H10C H 0.6693 0.4180 0.2286 0.072 Uiso 1 1 calc R . . C11 C 0.94170(12) 0.16579(16) 0.22768(12) 0.0269(5) Uani 1 1 d . . . C12 C 0.96504(12) 0.22400(16) 0.16472(13) 0.0301(5) Uani 1 1 d . . . C13 C 1.04746(12) 0.22379(18) 0.16426(14) 0.0354(5) Uani 1 1 d . . . H13 H 1.0642 0.2624 0.1215 0.042 Uiso 1 1 calc R . . C14 C 1.10598(13) 0.16943(19) 0.22384(15) 0.0394(6) Uani 1 1 d . . . C15 C 1.08011(13) 0.11228(18) 0.28485(15) 0.0381(6) Uani 1 1 d . . . H15 H 1.1191 0.0738 0.3256 0.046 Uiso 1 1 calc R . . C16 C 0.99882(13) 0.10958(17) 0.28823(13) 0.0327(5) Uani 1 1 d . . . C17 C 0.90529(13) 0.28592(18) 0.09956(14) 0.0370(5) Uani 1 1 d . . . H17A H 0.8725 0.2371 0.0583 0.055 Uiso 1 1 calc R . . H17B H 0.9348 0.3346 0.0708 0.055 Uiso 1 1 calc R . . H17C H 0.8695 0.3266 0.1269 0.055 Uiso 1 1 calc R . . C18 C 1.19506(14) 0.1725(2) 0.22329(18) 0.0558(7) Uani 1 1 d . . . H18A H 1.2009 0.1590 0.1660 0.084 Uiso 1 1 calc R . . H18B H 1.2246 0.1181 0.2615 0.084 Uiso 1 1 calc R . . H18C H 1.2175 0.2425 0.2419 0.084 Uiso 1 1 calc R . . C19 C 0.97416(14) 0.0476(2) 0.35719(15) 0.0447(6) Uani 1 1 d . . . H19A H 1.0167 -0.0041 0.3811 0.067 Uiso 1 1 calc R . . H19B H 0.9228 0.0105 0.3336 0.067 Uiso 1 1 calc R . . H19C H 0.9670 0.0964 0.4015 0.067 Uiso 1 1 calc R . . C20 C 0.82949(12) 0.01936(15) 0.08848(12) 0.0249(4) Uani 1 1 d . . . C21 C 0.86803(12) -0.05294(16) 0.14926(13) 0.0291(5) Uani 1 1 d . . . H21 H 0.8548 -0.0558 0.2024 0.035 Uiso 1 1 calc R . . C22 C 0.92612(13) -0.12102(16) 0.13150(14) 0.0329(5) Uani 1 1 d . . . H22 H 0.9541 -0.1691 0.1733 0.039 Uiso 1 1 calc R . . C23 C 0.94322(14) -0.11901(18) 0.05348(15) 0.0371(5) Uani 1 1 d . . . H23 H 0.9827 -0.1661 0.0414 0.045 Uiso 1 1 calc R . . C24 C 0.90329(14) -0.04889(18) -0.00723(14) 0.0370(5) Uani 1 1 d . . . H24 H 0.9150 -0.0486 -0.0612 0.044 Uiso 1 1 calc R . . C25 C 0.84614(12) 0.02120(16) 0.00962(13) 0.0294(5) Uani 1 1 d . . . H25 H 0.8188 0.0697 -0.0322 0.035 Uiso 1 1 calc R . . C26 C 0.69586(12) 0.10988(16) 0.04373(12) 0.0269(5) Uani 1 1 d . . . C27 C 0.64799(13) 0.02269(19) 0.01414(14) 0.0387(6) Uani 1 1 d . . . H27 H 0.6635 -0.0456 0.0369 0.046 Uiso 1 1 calc R . . C28 C 0.57731(14) 0.0354(2) -0.04892(15) 0.0465(6) Uani 1 1 d . . . H28 H 0.5434 -0.0240 -0.0685 0.056 Uiso 1 1 calc R . . C29 C 0.55638(14) 0.1340(2) -0.08297(15) 0.0472(7) Uani 1 1 d . . . H29 H 0.5080 0.1425 -0.1263 0.057 Uiso 1 1 calc R . . C30 C 0.60517(14) 0.2209(2) -0.05469(14) 0.0413(6) Uani 1 1 d . . . H30 H 0.5908 0.2887 -0.0792 0.050 Uiso 1 1 calc R . . C31 C 0.67488(13) 0.20898(18) 0.00929(13) 0.0334(5) Uani 1 1 d . . . H31 H 0.7082 0.2686 0.0295 0.040 Uiso 1 1 calc R . . N1 N 0.73709(9) 0.21095(13) 0.21071(10) 0.0256(4) Uani 1 1 d . . . N2 N 0.85936(9) 0.16707(13) 0.23516(10) 0.0265(4) Uani 1 1 d . . . N3 N 0.77132(10) 0.09373(13) 0.10686(10) 0.0257(4) Uani 1 1 d . . . Cl1 Cl 0.84650(3) 0.37882(4) 0.29036(4) 0.04137(18) Uani 1 1 d . . . Cl2 Cl 0.80183(3) 0.19421(5) 0.38722(3) 0.04180(18) Uani 1 1 d . . . B B 0.81177(15) 0.2407(2) 0.28373(15) 0.0315(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0229(10) 0.0300(11) 0.0221(10) -0.0003(8) 0.0083(8) -0.0031(9) C2 0.0203(10) 0.0372(12) 0.0244(10) -0.0051(9) 0.0080(8) -0.0023(9) C3 0.0262(11) 0.0388(12) 0.0238(10) -0.0022(9) 0.0064(9) 0.0001(10) C4 0.0322(12) 0.0446(14) 0.0369(13) -0.0035(10) 0.0113(10) -0.0108(11) C5 0.0269(12) 0.0548(16) 0.0394(13) -0.0071(11) 0.0128(10) -0.0030(11) C6 0.0288(12) 0.0491(15) 0.0401(13) -0.0052(11) 0.0098(10) 0.0077(11) C7 0.0316(12) 0.0407(13) 0.0283(11) -0.0019(10) 0.0104(9) 0.0007(10) C8 0.0352(12) 0.0381(13) 0.0379(13) 0.0056(10) 0.0105(10) -0.0054(11) C9 0.0289(13) 0.079(2) 0.080(2) -0.0020(16) 0.0231(14) -0.0023(13) C10 0.0434(14) 0.0386(14) 0.0667(17) 0.0067(12) 0.0242(13) 0.0136(11) C11 0.0255(11) 0.0309(11) 0.0256(11) -0.0081(9) 0.0087(9) -0.0036(9) C12 0.0282(11) 0.0350(12) 0.0278(11) -0.0082(9) 0.0082(9) -0.0020(9) C13 0.0317(12) 0.0434(13) 0.0364(12) -0.0129(10) 0.0188(10) -0.0074(10) C14 0.0269(12) 0.0469(14) 0.0461(14) -0.0167(11) 0.0124(11) -0.0025(11) C15 0.0263(12) 0.0432(13) 0.0420(14) -0.0070(11) 0.0028(10) 0.0050(10) C16 0.0283(11) 0.0352(12) 0.0341(12) -0.0041(10) 0.0068(10) 0.0013(10) C17 0.0370(13) 0.0442(13) 0.0318(12) -0.0001(10) 0.0122(10) -0.0092(11) C18 0.0289(13) 0.0753(19) 0.0671(18) -0.0175(15) 0.0195(12) -0.0025(13) C19 0.0384(13) 0.0475(14) 0.0464(14) 0.0103(12) 0.0065(11) 0.0046(11) C20 0.0216(10) 0.0275(11) 0.0262(11) -0.0051(8) 0.0071(8) -0.0031(9) C21 0.0291(11) 0.0341(12) 0.0252(11) -0.0019(9) 0.0088(9) -0.0027(10) C22 0.0344(12) 0.0307(11) 0.0340(12) 0.0010(9) 0.0092(10) 0.0011(10) C23 0.0347(12) 0.0348(12) 0.0443(14) -0.0086(10) 0.0142(11) 0.0017(10) C24 0.0411(13) 0.0431(13) 0.0307(12) -0.0069(10) 0.0160(10) -0.0017(11) C25 0.0289(11) 0.0346(12) 0.0260(11) -0.0022(9) 0.0091(9) 0.0031(9) C26 0.0225(10) 0.0377(12) 0.0220(10) -0.0023(9) 0.0085(8) 0.0004(9) C27 0.0376(13) 0.0442(14) 0.0322(12) -0.0024(10) 0.0045(10) -0.0038(11) C28 0.0372(14) 0.0588(17) 0.0389(14) -0.0091(12) 0.0004(11) -0.0129(12) C29 0.0275(12) 0.0762(19) 0.0346(13) 0.0033(13) 0.0009(10) 0.0021(13) C30 0.0378(13) 0.0504(15) 0.0339(13) 0.0055(11) 0.0052(11) 0.0099(12) C31 0.0293(11) 0.0423(13) 0.0291(11) -0.0009(10) 0.0081(9) -0.0015(10) N1 0.0213(8) 0.0336(10) 0.0239(9) -0.0045(7) 0.0095(7) -0.0007(7) N2 0.0229(9) 0.0356(10) 0.0215(9) -0.0034(7) 0.0062(7) -0.0018(8) N3 0.0225(9) 0.0337(9) 0.0213(8) -0.0031(7) 0.0063(7) 0.0020(7) Cl1 0.0394(3) 0.0393(3) 0.0468(4) -0.0147(3) 0.0132(3) -0.0081(3) Cl2 0.0405(3) 0.0620(4) 0.0249(3) -0.0055(3) 0.0118(2) -0.0034(3) B 0.0289(13) 0.0412(14) 0.0262(12) -0.0065(11) 0.0100(10) -0.0027(11) _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 C1 N3 1.342(2) . ? C1 N1 1.346(3) . ? C1 N2 1.353(2) . ? C2 C7 1.394(3) . ? C2 C3 1.412(3) . ? C2 N1 1.434(2) . ? C3 C4 1.394(3) . ? C3 C8 1.508(3) . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.372(3) . ? C5 C9 1.521(3) . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C10 1.498(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.397(3) . ? C11 C12 1.398(3) . ? C11 N2 1.428(3) . ? C12 C13 1.397(3) . ? C12 C17 1.498(3) . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 C18 1.510(3) . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C19 1.512(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.386(3) . ? C20 C21 1.389(3) . ? C20 N3 1.443(3) . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 C23 1.376(3) . ? C22 H22 0.9500 . ? C23 C24 1.378(3) . ? C23 H23 0.9500 . ? C24 C25 1.386(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C31 1.381(3) . ? C26 C27 1.382(3) . ? C26 N3 1.448(2) . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 C29 1.373(4) . ? C28 H28 0.9500 . ? C29 C30 1.383(3) . ? C29 H29 0.9500 . ? C30 C31 1.382(3) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? N1 B 1.559(3) . ? N2 B 1.566(3) . ? Cl1 B 1.833(3) . ? Cl2 B 1.837(3) . ? 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 C1 N1 129.00(17) . . ? N3 C1 N2 129.84(18) . . ? N1 C1 N2 101.15(16) . . ? C7 C2 C3 121.14(18) . . ? C7 C2 N1 117.57(18) . . ? C3 C2 N1 121.18(17) . . ? C4 C3 C2 117.42(19) . . ? C4 C3 C8 120.14(19) . . ? C2 C3 C8 122.44(18) . . ? C5 C4 C3 122.5(2) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C6 C5 C4 118.2(2) . . ? C6 C5 C9 120.7(2) . . ? C4 C5 C9 121.1(2) . . ? C5 C6 C7 122.3(2) . . ? C5 C6 H6 118.8 . . ? C7 C6 H6 118.8 . . ? C2 C7 C6 118.4(2) . . ? C2 C7 C10 121.11(19) . . ? C6 C7 C10 120.5(2) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 121.19(19) . . ? C16 C11 N2 117.80(18) . . ? C12 C11 N2 120.91(18) . . ? C13 C12 C11 117.68(19) . . ? C13 C12 C17 120.0(2) . . ? C11 C12 C17 122.35(19) . . ? C14 C13 C12 122.7(2) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C15 C14 C13 117.7(2) . . ? C15 C14 C18 120.6(2) . . ? C13 C14 C18 121.7(2) . . ? C14 C15 C16 122.0(2) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C15 C16 C11 118.7(2) . . ? C15 C16 C19 119.8(2) . . ? C11 C16 C19 121.46(19) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 120.70(19) . . ? C25 C20 N3 119.10(18) . . ? C21 C20 N3 120.20(18) . . ? C22 C21 C20 119.31(19) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C23 C22 C21 120.1(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 120.6(2) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C20 C25 C24 118.9(2) . . ? C20 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C31 C26 C27 120.44(19) . . ? C31 C26 N3 120.84(18) . . ? C27 C26 N3 118.56(18) . . ? C26 C27 C28 119.7(2) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C29 C28 C27 119.8(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.6(2) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C31 C30 C29 119.8(2) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C26 C31 C30 119.7(2) . . ? C26 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C1 N1 C2 130.00(16) . . ? C1 N1 B 87.86(15) . . ? C2 N1 B 131.77(16) . . ? C1 N2 C11 131.87(17) . . ? C1 N2 B 87.31(15) . . ? C11 N2 B 133.07(16) . . ? C1 N3 C20 121.60(16) . . ? C1 N3 C26 120.19(16) . . ? C20 N3 C26 118.10(15) . . ? N1 B N2 83.69(14) . . ? N1 B Cl1 117.56(16) . . ? N2 B Cl1 113.36(16) . . ? N1 B Cl2 112.95(15) . . ? N2 B Cl2 116.84(17) . . ? Cl1 B Cl2 110.40(12) . . ? 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 C7 C2 C3 C4 -0.1(3) . . . . ? N1 C2 C3 C4 175.86(18) . . . . ? C7 C2 C3 C8 -179.89(19) . . . . ? N1 C2 C3 C8 -3.9(3) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C8 C3 C4 C5 -179.4(2) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C3 C4 C5 C9 178.6(2) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C9 C5 C6 C7 -179.7(2) . . . . ? C3 C2 C7 C6 -0.9(3) . . . . ? N1 C2 C7 C6 -176.97(18) . . . . ? C3 C2 C7 C10 177.9(2) . . . . ? N1 C2 C7 C10 1.8(3) . . . . ? C5 C6 C7 C2 1.2(3) . . . . ? C5 C6 C7 C10 -177.6(2) . . . . ? C16 C11 C12 C13 0.2(3) . . . . ? N2 C11 C12 C13 176.40(17) . . . . ? C16 C11 C12 C17 -179.34(19) . . . . ? N2 C11 C12 C17 -3.1(3) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C17 C12 C13 C14 178.9(2) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C12 C13 C14 C18 -178.5(2) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C18 C14 C15 C16 178.6(2) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C14 C15 C16 C19 -178.8(2) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? N2 C11 C16 C15 -176.42(18) . . . . ? C12 C11 C16 C19 179.2(2) . . . . ? N2 C11 C16 C19 2.8(3) . . . . ? C25 C20 C21 C22 2.5(3) . . . . ? N3 C20 C21 C22 -177.50(18) . . . . ? C20 C21 C22 C23 -2.1(3) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C22 C23 C24 C25 0.7(3) . . . . ? C21 C20 C25 C24 -1.4(3) . . . . ? N3 C20 C25 C24 178.69(18) . . . . ? C23 C24 C25 C20 -0.3(3) . . . . ? C31 C26 C27 C28 -1.8(3) . . . . ? N3 C26 C27 C28 -177.2(2) . . . . ? C26 C27 C28 C29 1.6(4) . . . . ? C27 C28 C29 C30 -0.2(4) . . . . ? C28 C29 C30 C31 -1.1(4) . . . . ? C27 C26 C31 C30 0.5(3) . . . . ? N3 C26 C31 C30 175.83(19) . . . . ? C29 C30 C31 C26 0.9(3) . . . . ? N3 C1 N1 C2 34.3(3) . . . . ? N2 C1 N1 C2 -146.86(19) . . . . ? N3 C1 N1 B -178.7(2) . . . . ? N2 C1 N1 B 0.15(17) . . . . ? C7 C2 N1 C1 -137.8(2) . . . . ? C3 C2 N1 C1 46.2(3) . . . . ? C7 C2 N1 B 89.1(3) . . . . ? C3 C2 N1 B -87.0(3) . . . . ? N3 C1 N2 C11 27.6(4) . . . . ? N1 C1 N2 C11 -151.3(2) . . . . ? N3 C1 N2 B 178.7(2) . . . . ? N1 C1 N2 B -0.15(17) . . . . ? C16 C11 N2 C1 -133.5(2) . . . . ? C12 C11 N2 C1 50.2(3) . . . . ? C16 C11 N2 B 87.8(3) . . . . ? C12 C11 N2 B -88.5(3) . . . . ? N1 C1 N3 C20 -168.75(19) . . . . ? N2 C1 N3 C20 12.7(3) . . . . ? N1 C1 N3 C26 15.1(3) . . . . ? N2 C1 N3 C26 -163.43(19) . . . . ? C25 C20 N3 C1 -131.9(2) . . . . ? C21 C20 N3 C1 48.2(3) . . . . ? C25 C20 N3 C26 44.4(2) . . . . ? C21 C20 N3 C26 -135.60(19) . . . . ? C31 C26 N3 C1 56.0(3) . . . . ? C27 C26 N3 C1 -128.7(2) . . . . ? C31 C26 N3 C20 -120.3(2) . . . . ? C27 C26 N3 C20 55.1(2) . . . . ? C1 N1 B N2 -0.13(15) . . . . ? C2 N1 B N2 145.9(2) . . . . ? C1 N1 B Cl1 112.96(17) . . . . ? C2 N1 B Cl1 -101.0(2) . . . . ? C1 N1 B Cl2 -116.64(17) . . . . ? C2 N1 B Cl2 29.4(3) . . . . ? C1 N2 B N1 0.13(14) . . . . ? C11 N2 B N1 150.7(2) . . . . ? C1 N2 B Cl1 -117.21(16) . . . . ? C11 N2 B Cl1 33.3(3) . . . . ? C1 N2 B Cl2 112.69(17) . . . . ? C11 N2 B Cl2 -96.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.378 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.070