# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Gomes, Pedro' _publ_contact_author_email pedro.t.gomes@ist.utl.pt _publ_section_title ; Syntheses and photophysical properties of new iminopyrrolyl boron complexes and their application in efficient single-layer non-doped OLEDs prepared by spin coating ; loop_ _publ_author_name P.Gomes D.Suresh C.Gomes 'R.di Paolo' A.Macanita M.Calhorda ; J.Morgado ; M.Duarte # Attachment '- CIF_BIminopyrrolyl_comps_4_and_5_PTGomes.cif' data_compound-4 _database_code_depnum_ccdc_archive 'CCDC 867381' #TrackingRef '- CIF_BIminopyrrolyl_comps_4_and_5_PTGomes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C23 H19 B N2' _chemical_formula_sum 'C23 H19 B N2' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour yellow _diffrn_ambient_temperature 150(2) _chemical_formula_weight 334.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? 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 17.7637(16) _cell_length_b 11.2623(10) _cell_length_c 18.0062(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.691(5) _cell_angle_gamma 90.00 _cell_volume 3602.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3731 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.19 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15888 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 26.60 _reflns_number_total 3696 _reflns_number_gt 2671 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP _computing_publication_material enCIFer _iucr_refine_instructions_details ; TITL S47_C2-c in C2/c CELL 0.71073 17.7637 11.2623 18.0062 90.000 90.691 90.000 ZERR 4.00 0.0016 0.0010 0.0015 0.000 0.005 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H B N UNIT 184 152 8 16 MERG 2 OMIT 0.00 180.00 OMIT 2 0 0 OMIT 0 0 2 OMIT 1 1 0 FMAP 2 PLAN 25 SIZE 0.20 0.20 0.40 ACTA BOND $H CONF WGHT 0.05830 0.29760 L.S. 4 TEMP -123.00 FVAR 0.07719 N1 4 0.229660 0.054353 0.385707 11.00000 0.02414 0.02366 = 0.02524 0.00065 0.00064 0.00177 N2 4 0.278961 0.049309 0.507945 11.00000 0.02202 0.02121 = 0.02372 0.00171 0.00178 0.00201 C2 1 0.174367 0.074110 0.437099 11.00000 0.02467 0.02099 = 0.02981 0.00019 0.00339 0.00209 C3 1 0.105092 0.081711 0.401212 11.00000 0.02376 0.02908 = 0.03720 -0.00052 -0.00278 0.00342 AFIX 43 H3 2 0.057590 0.094927 0.423440 11.00000 -1.20000 AFIX 0 C4 1 0.119200 0.066087 0.326163 11.00000 0.03096 0.03176 = 0.03417 -0.00015 -0.00887 0.00172 AFIX 43 H4 2 0.082735 0.067089 0.287138 11.00000 -1.20000 AFIX 0 C5 1 0.196236 0.048703 0.318277 11.00000 0.03175 0.02852 = 0.02509 -0.00047 -0.00350 0.00033 AFIX 43 H5 2 0.221209 0.035058 0.272706 11.00000 -1.20000 AFIX 0 C6 1 0.206640 0.071440 0.508593 11.00000 0.02453 0.02154 = 0.02743 0.00134 0.00512 0.00400 AFIX 43 H6 2 0.178984 0.084307 0.552701 11.00000 -1.20000 AFIX 0 C7 1 0.321481 0.039544 0.575767 11.00000 0.01981 0.02431 = 0.02237 0.00344 0.00329 -0.00079 C8 1 0.369083 -0.057042 0.586666 11.00000 0.03170 0.02971 = 0.02436 -0.00115 0.00283 0.00848 AFIX 43 H8 2 0.375357 -0.114471 0.548596 11.00000 -1.20000 AFIX 0 C9 1 0.407130 -0.068288 0.653667 11.00000 0.03248 0.03664 = 0.03001 0.00329 0.00197 0.01190 AFIX 43 H9 2 0.439655 -0.134141 0.661645 11.00000 -1.20000 AFIX 0 C10 1 0.398484 0.014812 0.709047 11.00000 0.02886 0.04069 = 0.02307 0.00296 -0.00002 0.00112 AFIX 43 H10 2 0.424484 0.005737 0.755111 11.00000 -1.20000 AFIX 0 C11 1 0.351936 0.111274 0.697390 11.00000 0.03597 0.03125 = 0.02601 -0.00411 0.00359 -0.00003 AFIX 43 H11 2 0.346313 0.169102 0.735331 11.00000 -1.20000 AFIX 0 C12 1 0.313522 0.124016 0.630795 11.00000 0.02856 0.02231 = 0.03157 0.00135 0.00308 0.00346 AFIX 43 H12 2 0.281684 0.190690 0.622793 11.00000 -1.20000 AFIX 0 C13 1 0.342569 -0.091440 0.405799 11.00000 0.02530 0.02360 = 0.01838 0.00198 0.00131 0.00101 C14 1 0.418751 -0.111209 0.393063 11.00000 0.02587 0.02676 = 0.02432 0.00132 -0.00063 0.00224 AFIX 43 H14 2 0.452707 -0.046202 0.396360 11.00000 -1.20000 AFIX 0 C15 1 0.446600 -0.222641 0.375740 11.00000 0.03002 0.03200 = 0.03318 0.00125 0.00134 0.01002 AFIX 43 H15 2 0.498752 -0.232960 0.366606 11.00000 -1.20000 AFIX 0 C16 1 0.398334 -0.318671 0.371788 11.00000 0.04830 0.02394 = 0.03329 -0.00011 -0.00017 0.01123 AFIX 43 H16 2 0.417257 -0.395468 0.360706 11.00000 -1.20000 AFIX 0 C17 1 0.322561 -0.302470 0.384011 11.00000 0.04275 0.02258 = 0.04097 0.00293 0.00142 -0.00358 AFIX 43 H17 2 0.289113 -0.368166 0.381065 11.00000 -1.20000 AFIX 0 C18 1 0.295071 -0.190363 0.400609 11.00000 0.02960 0.02765 = 0.03501 0.00244 0.00522 0.00026 AFIX 43 H18 2 0.242687 -0.180486 0.408655 11.00000 -1.20000 AFIX 0 C19 1 0.364816 0.148679 0.404794 11.00000 0.02480 0.02062 = 0.02607 -0.00251 0.00603 0.00505 C20 1 0.423511 0.184823 0.452278 11.00000 0.02792 0.02867 = 0.02955 -0.00086 0.00555 -0.00002 AFIX 43 H20 2 0.430335 0.145221 0.498454 11.00000 -1.20000 AFIX 0 C21 1 0.471955 0.276516 0.434053 11.00000 0.02901 0.03087 = 0.04026 -0.00925 0.00677 -0.00286 AFIX 43 H21 2 0.511075 0.298961 0.467644 11.00000 -1.20000 AFIX 0 C22 1 0.463462 0.335379 0.367091 11.00000 0.03490 0.02231 = 0.05193 -0.00202 0.01669 -0.00321 AFIX 43 H22 2 0.496560 0.398235 0.354373 11.00000 -1.20000 AFIX 0 C23 1 0.406226 0.301648 0.318885 11.00000 0.04357 0.02879 = 0.03631 0.00930 0.00999 0.00287 AFIX 43 H23 2 0.399947 0.341338 0.272669 11.00000 -1.20000 AFIX 0 C24 1 0.357943 0.210053 0.337776 11.00000 0.03278 0.02646 = 0.02968 0.00006 0.00431 0.00286 AFIX 43 H24 2 0.318869 0.188371 0.303935 11.00000 -1.20000 AFIX 0 B1 3 0.309313 0.038659 0.422980 11.00000 0.02190 0.02525 = 0.02208 0.00151 0.00033 0.00126 HKLF 4 END ; _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^ > 2\s(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^)+(0.0583P)^2^+0.2976P] 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 3696 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.22966(6) 0.05435(9) 0.38571(6) 0.0243(3) Uani 1 1 d . . . N2 N 0.27896(6) 0.04931(9) 0.50795(6) 0.0223(3) Uani 1 1 d . . . C2 C 0.17437(8) 0.07411(11) 0.43710(8) 0.0251(3) Uani 1 1 d . . . C3 C 0.10509(8) 0.08171(12) 0.40121(8) 0.0300(3) Uani 1 1 d . . . H3 H 0.0576 0.0949 0.4234 0.036 Uiso 1 1 calc R . . C4 C 0.11920(8) 0.06609(12) 0.32616(8) 0.0324(4) Uani 1 1 d . . . H4 H 0.0827 0.0671 0.2871 0.039 Uiso 1 1 calc R . . C5 C 0.19624(8) 0.04870(12) 0.31828(8) 0.0285(3) Uani 1 1 d . . . H5 H 0.2212 0.0351 0.2727 0.034 Uiso 1 1 calc R . . C6 C 0.20664(7) 0.07144(11) 0.50859(7) 0.0245(3) Uani 1 1 d . . . H6 H 0.1790 0.0843 0.5527 0.029 Uiso 1 1 calc R . . C7 C 0.32148(7) 0.03954(11) 0.57577(7) 0.0221(3) Uani 1 1 d . . . C8 C 0.36908(8) -0.05704(12) 0.58667(8) 0.0286(3) Uani 1 1 d . . . H8 H 0.3754 -0.1145 0.5486 0.034 Uiso 1 1 calc R . . C9 C 0.40713(8) -0.06829(13) 0.65367(8) 0.0330(4) Uani 1 1 d . . . H9 H 0.4397 -0.1341 0.6616 0.040 Uiso 1 1 calc R . . C10 C 0.39848(8) 0.01481(13) 0.70905(8) 0.0309(3) Uani 1 1 d . . . H10 H 0.4245 0.0057 0.7551 0.037 Uiso 1 1 calc R . . C11 C 0.35194(8) 0.11127(13) 0.69739(8) 0.0311(3) Uani 1 1 d . . . H11 H 0.3463 0.1691 0.7353 0.037 Uiso 1 1 calc R . . C12 C 0.31352(8) 0.12402(12) 0.63079(8) 0.0275(3) Uani 1 1 d . . . H12 H 0.2817 0.1907 0.6228 0.033 Uiso 1 1 calc R . . C13 C 0.34257(7) -0.09144(11) 0.40580(7) 0.0224(3) Uani 1 1 d . . . C14 C 0.41875(8) -0.11121(12) 0.39306(7) 0.0257(3) Uani 1 1 d . . . H14 H 0.4527 -0.0462 0.3964 0.031 Uiso 1 1 calc R . . C15 C 0.44660(8) -0.22264(13) 0.37574(8) 0.0317(3) Uani 1 1 d . . . H15 H 0.4988 -0.2330 0.3666 0.038 Uiso 1 1 calc R . . C16 C 0.39833(9) -0.31867(13) 0.37179(8) 0.0352(4) Uani 1 1 d . . . H16 H 0.4173 -0.3955 0.3607 0.042 Uiso 1 1 calc R . . C17 C 0.32256(9) -0.30247(12) 0.38401(9) 0.0354(4) Uani 1 1 d . . . H17 H 0.2891 -0.3682 0.3811 0.043 Uiso 1 1 calc R . . C18 C 0.29507(9) -0.19036(12) 0.40061(8) 0.0307(3) Uani 1 1 d . . . H18 H 0.2427 -0.1805 0.4087 0.037 Uiso 1 1 calc R . . C19 C 0.36482(7) 0.14868(11) 0.40479(7) 0.0238(3) Uani 1 1 d . . . C20 C 0.42351(8) 0.18482(12) 0.45228(8) 0.0287(3) Uani 1 1 d . . . H20 H 0.4303 0.1452 0.4985 0.034 Uiso 1 1 calc R . . C21 C 0.47196(8) 0.27652(12) 0.43405(9) 0.0333(4) Uani 1 1 d . . . H21 H 0.5111 0.2990 0.4676 0.040 Uiso 1 1 calc R . . C22 C 0.46346(9) 0.33538(13) 0.36709(9) 0.0363(4) Uani 1 1 d . . . H22 H 0.4966 0.3982 0.3544 0.044 Uiso 1 1 calc R . . C23 C 0.40623(9) 0.30165(12) 0.31888(9) 0.0361(4) Uani 1 1 d . . . H23 H 0.3999 0.3413 0.2727 0.043 Uiso 1 1 calc R . . C24 C 0.35794(8) 0.21005(12) 0.33778(8) 0.0296(3) Uani 1 1 d . . . H24 H 0.3189 0.1884 0.3039 0.036 Uiso 1 1 calc R . . B1 B 0.30931(8) 0.03866(13) 0.42298(8) 0.0231(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 N1 0.0241(6) 0.0237(6) 0.0252(6) 0.0007(5) 0.0006(5) 0.0018(5) N2 0.0220(6) 0.0212(6) 0.0237(6) 0.0017(4) 0.0018(4) 0.0020(5) C2 0.0247(7) 0.0210(7) 0.0298(8) 0.0002(6) 0.0034(6) 0.0021(6) C3 0.0238(8) 0.0291(7) 0.0372(9) -0.0005(6) -0.0028(6) 0.0034(6) C4 0.0310(8) 0.0318(8) 0.0342(9) -0.0002(6) -0.0089(6) 0.0017(6) C5 0.0317(8) 0.0285(7) 0.0251(8) -0.0005(6) -0.0035(6) 0.0003(6) C6 0.0245(8) 0.0215(7) 0.0274(8) 0.0013(5) 0.0051(5) 0.0040(6) C7 0.0198(7) 0.0243(7) 0.0224(7) 0.0034(5) 0.0033(5) -0.0008(5) C8 0.0317(8) 0.0297(7) 0.0244(7) -0.0012(6) 0.0028(6) 0.0085(6) C9 0.0325(8) 0.0366(8) 0.0300(8) 0.0033(6) 0.0020(6) 0.0119(7) C10 0.0289(8) 0.0407(8) 0.0231(8) 0.0030(6) 0.0000(6) 0.0011(7) C11 0.0360(9) 0.0312(7) 0.0260(8) -0.0041(6) 0.0036(6) 0.0000(7) C12 0.0286(8) 0.0223(7) 0.0316(8) 0.0013(6) 0.0031(6) 0.0035(6) C13 0.0253(7) 0.0236(7) 0.0184(7) 0.0020(5) 0.0013(5) 0.0010(6) C14 0.0259(7) 0.0268(7) 0.0243(7) 0.0013(6) -0.0006(5) 0.0022(6) C15 0.0300(8) 0.0320(8) 0.0332(9) 0.0012(6) 0.0013(6) 0.0100(6) C16 0.0483(10) 0.0239(7) 0.0333(9) -0.0001(6) -0.0002(7) 0.0112(7) C17 0.0428(10) 0.0226(7) 0.0410(9) 0.0029(6) 0.0014(7) -0.0036(7) C18 0.0296(8) 0.0277(8) 0.0350(9) 0.0024(6) 0.0052(6) 0.0003(6) C19 0.0248(8) 0.0206(7) 0.0261(7) -0.0025(5) 0.0060(5) 0.0050(5) C20 0.0279(8) 0.0287(7) 0.0296(8) -0.0009(6) 0.0056(6) 0.0000(6) C21 0.0290(8) 0.0309(8) 0.0403(9) -0.0092(7) 0.0068(6) -0.0029(6) C22 0.0349(9) 0.0223(7) 0.0519(10) -0.0020(7) 0.0167(7) -0.0032(6) C23 0.0436(10) 0.0288(8) 0.0363(9) 0.0093(6) 0.0100(7) 0.0029(7) C24 0.0328(8) 0.0265(7) 0.0297(8) 0.0001(6) 0.0043(6) 0.0029(6) B1 0.0219(8) 0.0253(8) 0.0221(8) 0.0015(6) 0.0003(6) 0.0013(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3466(17) . ? N1 C2 1.3757(17) . ? N1 B1 1.5687(18) . ? N2 C6 1.3088(16) . ? N2 C7 1.4324(16) . ? N2 B1 1.6327(19) . ? C2 C3 1.3857(19) . ? C2 C6 1.4032(19) . ? C3 C4 1.389(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.3821(19) . ? C7 C8 1.3902(18) . ? C8 C9 1.3815(19) . ? C8 H8 0.9500 . ? C9 C10 1.378(2) . ? C9 H9 0.9500 . ? C10 C11 1.380(2) . ? C10 H10 0.9500 . ? C11 C12 1.3800(19) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.3932(19) . ? C13 C18 1.4000(19) . ? C13 B1 1.6112(19) . ? C14 C15 1.3859(19) . ? C14 H14 0.9500 . ? C15 C16 1.381(2) . ? C15 H15 0.9500 . ? C16 C17 1.379(2) . ? C16 H16 0.9500 . ? C17 C18 1.388(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.3948(19) . ? C19 C20 1.4008(19) . ? C19 B1 1.619(2) . ? C20 C21 1.386(2) . ? C20 H20 0.9500 . ? C21 C22 1.383(2) . ? C21 H21 0.9500 . ? C22 C23 1.382(2) . ? C22 H22 0.9500 . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 H24 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 C5 N1 C2 107.67(11) . . ? C5 N1 B1 140.00(12) . . ? C2 N1 B1 112.21(11) . . ? C6 N2 C7 120.97(11) . . ? C6 N2 B1 110.95(11) . . ? C7 N2 B1 128.07(11) . . ? N1 C2 C3 109.48(12) . . ? N1 C2 C6 109.06(11) . . ? C3 C2 C6 141.25(13) . . ? C2 C3 C4 106.04(13) . . ? C2 C3 H3 127.0 . . ? C4 C3 H3 127.0 . . ? C3 C4 C5 107.84(13) . . ? C3 C4 H4 126.1 . . ? C5 C4 H4 126.1 . . ? N1 C5 C4 108.96(13) . . ? N1 C5 H5 125.5 . . ? C4 C5 H5 125.5 . . ? N2 C6 C2 112.71(12) . . ? N2 C6 H6 123.6 . . ? C2 C6 H6 123.6 . . ? C12 C7 C8 120.31(12) . . ? C12 C7 N2 120.06(11) . . ? C8 C7 N2 119.60(11) . . ? C9 C8 C7 119.03(13) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 120.81(13) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.78(13) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.21(13) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 119.84(13) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C14 C13 C18 116.59(12) . . ? C14 C13 B1 122.42(12) . . ? C18 C13 B1 120.96(12) . . ? C15 C14 C13 122.13(13) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C16 C15 C14 119.84(14) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 119.65(13) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.11(14) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 121.67(14) . . ? C17 C18 H18 119.2 . . ? C13 C18 H18 119.2 . . ? C24 C19 C20 116.15(13) . . ? C24 C19 B1 120.46(12) . . ? C20 C19 B1 123.33(12) . . ? C21 C20 C19 122.11(14) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C22 C21 C20 120.14(14) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 119.18(14) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 120.20(14) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 122.21(14) . . ? C23 C24 H24 118.9 . . ? C19 C24 H24 118.9 . . ? N1 B1 C13 110.56(11) . . ? N1 B1 C19 112.05(11) . . ? C13 B1 C19 115.56(11) . . ? N1 B1 N2 94.95(10) . . ? C13 B1 N2 111.88(10) . . ? C19 B1 N2 110.00(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 -0.37(14) . . . . ? B1 N1 C2 C3 -177.25(11) . . . . ? C5 N1 C2 C6 175.55(11) . . . . ? B1 N1 C2 C6 -1.33(14) . . . . ? N1 C2 C3 C4 -0.01(15) . . . . ? C6 C2 C3 C4 -173.83(17) . . . . ? C2 C3 C4 C5 0.37(15) . . . . ? C2 N1 C5 C4 0.60(15) . . . . ? B1 N1 C5 C4 176.10(14) . . . . ? C3 C4 C5 N1 -0.61(16) . . . . ? C7 N2 C6 C2 -178.15(11) . . . . ? B1 N2 C6 C2 2.96(15) . . . . ? N1 C2 C6 N2 -1.11(15) . . . . ? C3 C2 C6 N2 172.74(16) . . . . ? C6 N2 C7 C12 -47.21(17) . . . . ? B1 N2 C7 C12 131.47(13) . . . . ? C6 N2 C7 C8 130.98(14) . . . . ? B1 N2 C7 C8 -50.33(18) . . . . ? C12 C7 C8 C9 1.1(2) . . . . ? N2 C7 C8 C9 -177.04(13) . . . . ? C7 C8 C9 C10 -0.2(2) . . . . ? C8 C9 C10 C11 -0.7(2) . . . . ? C9 C10 C11 C12 0.7(2) . . . . ? C10 C11 C12 C7 0.3(2) . . . . ? C8 C7 C12 C11 -1.2(2) . . . . ? N2 C7 C12 C11 176.98(12) . . . . ? C18 C13 C14 C15 0.31(19) . . . . ? B1 C13 C14 C15 -177.68(12) . . . . ? C13 C14 C15 C16 -1.0(2) . . . . ? C14 C15 C16 C17 1.0(2) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? C16 C17 C18 C13 -0.3(2) . . . . ? C14 C13 C18 C17 0.3(2) . . . . ? B1 C13 C18 C17 178.36(13) . . . . ? C24 C19 C20 C21 0.2(2) . . . . ? B1 C19 C20 C21 177.54(13) . . . . ? C19 C20 C21 C22 -0.2(2) . . . . ? C20 C21 C22 C23 0.0(2) . . . . ? C21 C22 C23 C24 0.2(2) . . . . ? C22 C23 C24 C19 -0.2(2) . . . . ? C20 C19 C24 C23 0.0(2) . . . . ? B1 C19 C24 C23 -177.41(13) . . . . ? C5 N1 B1 C13 -57.2(2) . . . . ? C2 N1 B1 C13 118.22(12) . . . . ? C5 N1 B1 C19 73.33(19) . . . . ? C2 N1 B1 C19 -111.30(12) . . . . ? C5 N1 B1 N2 -172.75(14) . . . . ? C2 N1 B1 N2 2.62(12) . . . . ? C14 C13 B1 N1 143.12(12) . . . . ? C18 C13 B1 N1 -34.79(17) . . . . ? C14 C13 B1 C19 14.51(18) . . . . ? C18 C13 B1 C19 -163.40(12) . . . . ? C14 C13 B1 N2 -112.41(13) . . . . ? C18 C13 B1 N2 69.68(15) . . . . ? C24 C19 B1 N1 -30.90(17) . . . . ? C20 C19 B1 N1 151.87(12) . . . . ? C24 C19 B1 C13 96.96(15) . . . . ? C20 C19 B1 C13 -80.26(16) . . . . ? C24 C19 B1 N2 -135.18(12) . . . . ? C20 C19 B1 N2 47.60(16) . . . . ? C6 N2 B1 N1 -3.27(12) . . . . ? C7 N2 B1 N1 177.94(11) . . . . ? C6 N2 B1 C13 -117.77(12) . . . . ? C7 N2 B1 C13 63.44(16) . . . . ? C6 N2 B1 C19 112.36(12) . . . . ? C7 N2 B1 C19 -66.43(15) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 26.60 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.230 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.039 ####################################################### data_compound-5 _database_code_depnum_ccdc_archive 'CCDC 867382' #TrackingRef '- CIF_BIminopyrrolyl_comps_4_and_5_PTGomes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C40 H32 B2 N4, 2(C H2 Cl2)' _chemical_formula_sum 'C42 H36 B2 Cl4 N4' _chemical_melting_point ? _exptl_crystal_description Prism _exptl_crystal_colour Yellow _diffrn_ambient_temperature 150(2) _chemical_formula_weight 760.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1967(3) _cell_length_b 11.7901(4) _cell_length_c 19.9616(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.809(2) _cell_angle_gamma 90.00 _cell_volume 1919.18(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6339 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 25.15 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8198 _exptl_absorpt_correction_T_max 0.9036 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21705 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.75 _reflns_number_total 3654 _reflns_number_gt 2828 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP _computing_publication_material enCIFer _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^ > 2\s(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. ; _iucr_refine_instructions_details ; TITL S48_P21-n in P2(1)/n CELL 0.71073 8.1967 11.7901 19.9616 90.000 95.809 90.000 ZERR 2.00 0.0003 0.0004 0.0006 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H B N O CL UNIT 84 72 4 8 0 8 MERG 2 OMIT 0.00 180.00 OMIT 0 2 4 OMIT 3 0 3 OMIT 0 0 2 OMIT 0 1 1 OMIT 0 4 6 OMIT 4 4 0 OMIT 2 3 0 OMIT 0 0 8 OMIT -6 0 6 OMIT 0 6 9 OMIT 0 10 13 OMIT 0 8 10 OMIT 5 0 5 OMIT 0 5 10 OMIT -5 0 15 OMIT 0 7 12 OMIT 0 7 11 OMIT 2 5 0 OMIT -6 0 20 OMIT 1 0 7 FMAP 2 PLAN 25 SIZE 0.30 0.40 0.60 ACTA WGHT 0.05810 1.36050 L.S. 4 TEMP -123.00 FVAR 0.19151 0.42958 N1 4 -0.032020 0.045832 0.842442 11.00000 0.02292 0.03229 = 0.02475 0.00043 0.00483 -0.00079 N2 4 0.199399 0.038126 0.922351 11.00000 0.02104 0.02628 = 0.02254 -0.00078 0.00586 -0.00154 C2 1 -0.036895 0.129866 0.890188 11.00000 0.02426 0.03018 = 0.02651 0.00111 0.00785 -0.00055 C3 1 -0.174098 0.197985 0.874036 11.00000 0.02534 0.03530 = 0.03412 0.00340 0.00835 0.00472 AFIX 43 H3 2 -0.206347 0.260541 0.897833 11.00000 -1.20000 AFIX 0 C4 1 -0.252567 0.153240 0.815178 11.00000 0.02285 0.04685 = 0.03436 0.00780 0.00352 0.00394 AFIX 43 H4 2 -0.348578 0.180666 0.791961 11.00000 -1.20000 AFIX 0 C5 1 -0.162787 0.060198 0.796865 11.00000 0.02538 0.04356 = 0.02669 0.00024 0.00064 -0.00252 AFIX 43 H5 2 -0.189009 0.015072 0.759096 11.00000 -1.20000 AFIX 0 C6 1 0.103255 0.121234 0.936581 11.00000 0.02520 0.02684 = 0.02501 -0.00092 0.00793 -0.00173 AFIX 43 H6 2 0.125181 0.169305 0.973327 11.00000 -1.20000 AFIX 0 C7 1 0.351543 0.017588 0.961867 11.00000 0.02132 0.02136 = 0.02682 -0.00138 0.00454 -0.00172 C8 1 0.493637 0.001540 0.930259 11.00000 0.02681 0.03065 = 0.02168 -0.00090 0.00717 -0.00176 AFIX 43 H8 2 0.489091 0.002368 0.883521 11.00000 -1.20000 AFIX 0 C9 1 0.358927 0.015578 1.031379 11.00000 0.02236 0.03096 = 0.02507 -0.00180 0.00932 0.00022 AFIX 43 H9 2 0.263784 0.025844 1.052385 11.00000 -1.20000 AFIX 0 C10 1 0.054755 -0.156158 0.888693 11.00000 0.03163 0.03005 = 0.02295 -0.00498 0.01083 -0.00310 C11 1 -0.104432 -0.195985 0.870994 11.00000 0.03161 0.03570 = 0.03632 -0.00440 0.01160 -0.00271 AFIX 43 H11 2 -0.175990 -0.152815 0.842216 11.00000 -1.20000 AFIX 0 C12 1 -0.158717 -0.298494 0.895278 11.00000 0.03776 0.03947 = 0.05011 -0.00722 0.01789 -0.01198 AFIX 43 H12 2 -0.265372 -0.322806 0.882728 11.00000 -1.20000 AFIX 0 C13 1 -0.055064 -0.363894 0.937768 11.00000 0.05720 0.03356 = 0.03999 -0.00139 0.02145 -0.01090 AFIX 43 H13 2 -0.091679 -0.432074 0.954279 11.00000 -1.20000 AFIX 0 C14 1 0.103131 -0.328063 0.955778 11.00000 0.05652 0.03323 = 0.02869 0.00199 0.00760 -0.00243 AFIX 43 H14 2 0.173962 -0.372406 0.984164 11.00000 -1.20000 AFIX 0 C15 1 0.157012 -0.225528 0.931514 11.00000 0.03804 0.03295 = 0.02842 -0.00036 0.00418 -0.00527 AFIX 43 H15 2 0.264195 -0.202396 0.944129 11.00000 -1.20000 AFIX 0 C16 1 0.234665 -0.046483 0.800276 11.00000 0.02190 0.02904 = 0.02168 -0.00191 0.00272 -0.00320 C17 1 0.265630 0.048414 0.762093 11.00000 0.03173 0.03052 = 0.02887 -0.00004 0.00652 0.00287 AFIX 43 H17 2 0.210115 0.115581 0.768864 11.00000 -1.20000 AFIX 0 C18 1 0.377451 0.045631 0.714008 11.00000 0.03564 0.03808 = 0.02963 0.00635 0.00966 -0.00321 AFIX 43 H18 2 0.395481 0.110150 0.688986 11.00000 -1.20000 AFIX 0 C19 1 0.461352 -0.053285 0.703666 11.00000 0.02813 0.04477 = 0.03013 -0.00482 0.01195 -0.00330 AFIX 43 H19 2 0.536801 -0.055491 0.671891 11.00000 -1.20000 AFIX 0 C20 1 0.432943 -0.148944 0.740631 11.00000 0.03299 0.03515 = 0.03857 -0.00490 0.01149 0.00128 AFIX 43 H20 2 0.489225 -0.215773 0.733809 11.00000 -1.20000 AFIX 0 C21 1 0.320134 -0.145208 0.788039 11.00000 0.03209 0.02862 = 0.03195 0.00084 0.00905 -0.00161 AFIX 43 H21 2 0.301153 -0.210432 0.812277 11.00000 -1.20000 AFIX 0 C22 1 1.074282 0.864065 0.613068 11.00000 0.06128 0.17509 = 0.09424 -0.04510 -0.02107 0.04749 AFIX 23 H22A 2 1.177437 0.904907 0.619212 11.00000 -1.20000 H22B 2 1.077635 0.805812 0.647495 11.00000 -1.20000 AFIX 0 B1 3 0.115028 -0.037104 0.859497 11.00000 0.02282 0.02972 = 0.02363 -0.00205 0.00392 0.00000 PART 1 CL1 6 0.913484 0.959992 0.626050 21.00000 0.03312 0.03329 = 0.04025 -0.01424 0.01316 0.00031 CL2 6 1.060381 0.802415 0.539641 21.00000 0.04310 0.08722 = 0.15751 -0.07278 0.00879 0.00567 PART 2 CL1A 6 0.933691 0.963559 0.624557 -21.00000 0.09128 0.13685 = 0.13129 -0.06703 0.00877 0.02757 CL2A 6 1.098876 0.840440 0.533191 -21.00000 0.17754 0.10638 = 0.07308 0.02806 0.07703 0.07964 HKLF 4 END ; _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^)+(0.0581P)^2^+1.3605P] 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 3654 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0320(2) 0.04583(15) 0.84245(8) 0.0266(4) Uani 1 1 d . . . N2 N 0.19941(19) 0.03813(14) 0.92235(8) 0.0232(4) Uani 1 1 d . . . C2 C -0.0369(2) 0.12987(18) 0.89019(10) 0.0267(5) Uani 1 1 d . . . C3 C -0.1741(2) 0.19801(19) 0.87406(11) 0.0313(5) Uani 1 1 d . . . H3 H -0.2071 0.2619 0.8984 0.038 Uiso 1 1 calc R . . C4 C -0.2526(3) 0.1533(2) 0.81516(11) 0.0347(5) Uani 1 1 d . . . H4 H -0.3507 0.1813 0.7914 0.042 Uiso 1 1 calc R . . C5 C -0.1628(3) 0.0602(2) 0.79684(11) 0.0321(5) Uani 1 1 d . . . H5 H -0.1896 0.0141 0.7583 0.039 Uiso 1 1 calc R . . C6 C 0.1033(2) 0.12126(17) 0.93660(10) 0.0254(4) Uani 1 1 d . . . H6 H 0.1257 0.1704 0.9741 0.031 Uiso 1 1 calc R . . C7 C 0.3515(2) 0.01759(16) 0.96187(10) 0.0231(4) Uani 1 1 d . . . C8 C 0.4936(2) 0.00154(18) 0.93023(10) 0.0262(4) Uani 1 1 d . . . H8 H 0.4890 0.0024 0.8825 0.031 Uiso 1 1 calc R . . C9 C 0.3589(2) 0.01558(17) 1.03139(10) 0.0258(5) Uani 1 1 d . . . H9 H 0.2617 0.0261 1.0528 0.031 Uiso 1 1 calc R . . C10 C 0.0547(3) -0.15616(18) 0.88869(10) 0.0278(5) Uani 1 1 d . . . C11 C -0.1045(3) -0.1960(2) 0.87098(11) 0.0341(5) Uani 1 1 d . . . H11 H -0.1776 -0.1518 0.8416 0.041 Uiso 1 1 calc R . . C12 C -0.1588(3) -0.2985(2) 0.89527(13) 0.0416(6) Uani 1 1 d . . . H12 H -0.2677 -0.3233 0.8824 0.050 Uiso 1 1 calc R . . C13 C -0.0551(3) -0.3639(2) 0.93778(12) 0.0425(6) Uani 1 1 d . . . H13 H -0.0925 -0.4336 0.9546 0.051 Uiso 1 1 calc R . . C14 C 0.1032(3) -0.3281(2) 0.95580(11) 0.0393(6) Uani 1 1 d . . . H14 H 0.1756 -0.3734 0.9848 0.047 Uiso 1 1 calc R . . C15 C 0.1571(3) -0.22552(19) 0.93152(11) 0.0332(5) Uani 1 1 d . . . H15 H 0.2666 -0.2019 0.9444 0.040 Uiso 1 1 calc R . . C16 C 0.2347(2) -0.04649(17) 0.80028(10) 0.0243(4) Uani 1 1 d . . . C17 C 0.2656(3) 0.04847(19) 0.76210(10) 0.0302(5) Uani 1 1 d . . . H17 H 0.2089 0.1171 0.7690 0.036 Uiso 1 1 calc R . . C18 C 0.3775(3) 0.0457(2) 0.71400(11) 0.0341(5) Uani 1 1 d . . . H18 H 0.3959 0.1116 0.6884 0.041 Uiso 1 1 calc R . . C19 C 0.4614(3) -0.0533(2) 0.70365(11) 0.0338(5) Uani 1 1 d . . . H19 H 0.5384 -0.0555 0.6712 0.041 Uiso 1 1 calc R . . C20 C 0.4330(3) -0.1490(2) 0.74063(11) 0.0351(5) Uani 1 1 d . . . H20 H 0.4905 -0.2172 0.7337 0.042 Uiso 1 1 calc R . . C21 C 0.3201(3) -0.14525(18) 0.78805(11) 0.0306(5) Uani 1 1 d . . . H21 H 0.3007 -0.2119 0.8128 0.037 Uiso 1 1 calc R . . C22 C 1.0743(5) 0.8640(5) 0.6131(2) 0.1117(17) Uani 1 1 d . . . H22A H 1.1796 0.9056 0.6195 0.134 Uiso 1 1 calc R A 1 H22B H 1.0775 0.8045 0.6482 0.134 Uiso 1 1 calc R A 1 B1 B 0.1150(3) -0.0371(2) 0.85949(11) 0.0254(5) Uani 1 1 d . . . Cl1 Cl 0.9136(4) 0.9600(2) 0.62606(14) 0.0348(8) Uani 0.429(9) 1 d P B 1 Cl2 Cl 1.0604(4) 0.8024(5) 0.5396(3) 0.0963(18) Uani 0.429(9) 1 d P B 1 Cl1A Cl 0.9336(7) 0.9636(4) 0.6245(2) 0.121(2) Uani 0.571(9) 1 d P B 2 Cl2A Cl 1.0989(7) 0.8404(4) 0.53320(16) 0.1150(16) Uani 0.571(9) 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0231(9) 0.0324(9) 0.0248(9) 0.0004(7) 0.0048(7) -0.0008(7) N2 0.0211(8) 0.0264(9) 0.0226(8) -0.0008(7) 0.0059(7) -0.0015(7) C2 0.0244(10) 0.0303(11) 0.0266(10) 0.0011(9) 0.0078(8) -0.0006(8) C3 0.0253(11) 0.0355(12) 0.0342(12) 0.0035(10) 0.0083(9) 0.0046(9) C4 0.0231(11) 0.0467(14) 0.0344(12) 0.0077(10) 0.0037(9) 0.0039(10) C5 0.0254(11) 0.0437(13) 0.0269(11) 0.0004(10) 0.0007(9) -0.0025(9) C6 0.0252(10) 0.0269(10) 0.0252(10) -0.0007(8) 0.0080(8) -0.0017(8) C7 0.0214(10) 0.0215(10) 0.0269(10) -0.0014(8) 0.0046(8) -0.0017(8) C8 0.0268(11) 0.0306(11) 0.0220(10) -0.0009(8) 0.0072(8) -0.0017(9) C9 0.0225(10) 0.0310(11) 0.0251(10) -0.0018(9) 0.0092(8) 0.0002(8) C10 0.0318(11) 0.0301(11) 0.0231(10) -0.0050(9) 0.0109(8) -0.0031(9) C11 0.0317(11) 0.0357(12) 0.0364(12) -0.0045(10) 0.0117(9) -0.0028(10) C12 0.0380(13) 0.0395(13) 0.0501(14) -0.0072(12) 0.0179(11) -0.0118(11) C13 0.0572(16) 0.0338(13) 0.0400(13) -0.0015(11) 0.0214(12) -0.0108(12) C14 0.0567(15) 0.0333(12) 0.0288(12) 0.0018(10) 0.0077(10) -0.0025(11) C15 0.0383(12) 0.0330(12) 0.0284(11) -0.0003(9) 0.0043(9) -0.0052(10) C16 0.0220(10) 0.0291(11) 0.0218(10) -0.0019(8) 0.0027(8) -0.0032(8) C17 0.0318(11) 0.0308(11) 0.0288(11) 0.0001(9) 0.0065(9) 0.0027(9) C18 0.0356(12) 0.0382(12) 0.0297(11) 0.0062(10) 0.0096(9) -0.0032(10) C19 0.0282(11) 0.0448(13) 0.0303(11) -0.0048(10) 0.0118(9) -0.0033(10) C20 0.0330(12) 0.0353(12) 0.0386(12) -0.0048(10) 0.0115(10) 0.0011(10) C21 0.0321(11) 0.0289(11) 0.0320(11) 0.0006(9) 0.0090(9) -0.0015(9) C22 0.061(2) 0.174(5) 0.094(3) -0.044(3) -0.021(2) 0.047(3) B1 0.0229(11) 0.0298(12) 0.0237(11) -0.0020(9) 0.0039(9) 0.0000(9) Cl1 0.0330(11) 0.0332(12) 0.0401(13) -0.0144(10) 0.0131(8) 0.0003(9) Cl2 0.0431(15) 0.087(3) 0.158(4) -0.073(3) 0.0086(17) 0.0058(14) Cl1A 0.092(3) 0.138(3) 0.132(3) -0.067(3) 0.009(2) 0.028(2) Cl2A 0.178(4) 0.107(3) 0.0732(17) 0.0282(15) 0.0772(19) 0.080(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.345(3) . ? N1 C2 1.378(3) . ? N1 B1 1.562(3) . ? N2 C6 1.307(3) . ? N2 C7 1.427(3) . ? N2 B1 1.632(3) . ? C2 C3 1.393(3) . ? C2 C6 1.405(3) . ? C3 C4 1.386(3) . ? C4 C5 1.391(3) . ? C7 C9 1.383(3) . ? C7 C8 1.393(3) . ? C8 C9 1.379(3) 3_657 ? C9 C8 1.379(3) 3_657 ? C10 C11 1.398(3) . ? C10 C15 1.400(3) . ? C10 B1 1.616(3) . ? C11 C12 1.392(3) . ? C12 C13 1.376(4) . ? C13 C14 1.377(4) . ? C14 C15 1.391(3) . ? C16 C17 1.392(3) . ? C16 C21 1.393(3) . ? C16 B1 1.614(3) . ? C17 C18 1.394(3) . ? C18 C19 1.380(3) . ? C19 C20 1.381(3) . ? C20 C21 1.390(3) . ? C22 Cl2 1.630(6) . ? C22 Cl2A 1.652(5) . ? C22 Cl1A 1.677(6) . ? C22 Cl1 1.775(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 C5 N1 C2 107.50(17) . . ? C5 N1 B1 140.39(18) . . ? C2 N1 B1 112.04(16) . . ? C6 N2 C7 121.29(17) . . ? C6 N2 B1 110.91(16) . . ? C7 N2 B1 127.68(16) . . ? N1 C2 C3 109.52(18) . . ? N1 C2 C6 108.97(17) . . ? C3 C2 C6 141.4(2) . . ? C4 C3 C2 105.7(2) . . ? C3 C4 C5 108.1(2) . . ? N1 C5 C4 109.1(2) . . ? N2 C6 C2 112.43(18) . . ? C9 C7 C8 119.94(18) . . ? C9 C7 N2 120.28(17) . . ? C8 C7 N2 119.77(17) . . ? C9 C8 C7 119.62(18) 3_657 . ? C8 C9 C7 120.44(18) 3_657 . ? C11 C10 C15 116.4(2) . . ? C11 C10 B1 120.8(2) . . ? C15 C10 B1 122.79(19) . . ? C12 C11 C10 121.8(2) . . ? C13 C12 C11 120.2(2) . . ? C12 C13 C14 119.7(2) . . ? C13 C14 C15 120.0(2) . . ? C14 C15 C10 121.9(2) . . ? C17 C16 C21 116.98(18) . . ? C17 C16 B1 120.24(18) . . ? C21 C16 B1 122.62(18) . . ? C16 C17 C18 121.8(2) . . ? C19 C18 C17 119.7(2) . . ? C18 C19 C20 119.80(19) . . ? C19 C20 C21 119.9(2) . . ? C20 C21 C16 121.8(2) . . ? Cl2 C22 Cl1A 116.6(3) . . ? Cl2A C22 Cl1A 113.7(3) . . ? Cl2 C22 Cl1 115.4(3) . . ? Cl2A C22 Cl1 114.4(3) . . ? N1 B1 C16 113.32(17) . . ? N1 B1 C10 111.40(16) . . ? C16 B1 C10 115.79(17) . . ? N1 B1 N2 94.87(15) . . ? C16 B1 N2 111.02(16) . . ? C10 B1 N2 108.42(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.672 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.050