Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Lacroix, P. G.' 'Farfan, N.' 'Munoz, Blanca M.' 'Nakatani, Keitaro' 'Reyes, Horacio' 'Rojas-Lima, Susana' 'Santillan, Rosa' _publ_contact_author_name 'Dr P G Lacroix' _publ_contact_author_address ; Laboratoire de Chimie de Coordination 205 route de Narbonne Toulouse Cedex 04 31077 FRANCE ; _publ_contact_author_email 'PASCAL@LCC-TOULOUSE.FR' _journal_name_full 'Journal of Materials chemistry' _publ_section_title ; Synthesis, crystal structures, and quadratic nonlinear optical (NLO) properties in a series of push-pull boronate derivatives ; data_1 _database_code_CSD 175921 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _audit_creation_date 2002-07-05T10:52:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO _chemical_name_systematic ; 2-(phenyl)-(3¥-nitrobenzo[d])-(4¥¥-diethylaminobenzo[h])-1,3-dioxa-6-aza-2 -boracyclonon-6-ene ' ; _chemical_formula_sum 'C23 H22 B N3 O4' _chemical_formula_weight 415.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2yac' _symmetry_Int_Tables_number 14 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 11.1674(4) _cell_length_b 7.7630(3) _cell_length_c 24.1683(9) _cell_angle_alpha 90 _cell_angle_beta 90.7300(10) _cell_angle_gamma 90 _cell_volume 2095.04(14) _cell_formula_units_Z 4 _cell_measurement_temperature 569(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 569(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_number 13417 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 4136 _reflns_number_gt 2982 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+0.0594P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_coef 0.066(3) _refine_ls_number_reflns 4136 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.125 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.173 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.20168(14) 0.9605(2) 0.20132(7) 0.0447(4) Uani 1 1 d . . . N1 N 0.06532(10) 0.95524(16) 0.21890(5) 0.0453(3) Uani 1 1 d . . . N2 N 0.37290(12) 0.7315(2) 0.42736(5) 0.0615(4) Uani 1 1 d . . . N3 N -0.13813(16) 0.7608(2) 0.01798(7) 0.0799(5) Uani 1 1 d . . . O2 O 0.26904(8) 0.85608(13) 0.24121(4) 0.0476(3) Uani 1 1 d . . . O1 O 0.19196(8) 0.87652(14) 0.14582(4) 0.0503(3) Uani 1 1 d . . . O4 O -0.06945(16) 0.7037(3) -0.01579(7) 0.1272(8) Uani 1 1 d . . . O3 O -0.24561(14) 0.7676(2) 0.01011(7) 0.1097(6) Uani 1 1 d . . . C7 C 0.03476(13) 0.94498(19) 0.27106(6) 0.0482(4) Uani 1 1 d . . . H7 H -0.045 0.9571 0.281 0.058 Uiso 1 1 calc R . . C1 C 0.12275(12) 0.91583(19) 0.31142(6) 0.0461(4) Uani 1 1 d . . . C2 C 0.23940(12) 0.86125(19) 0.29480(6) 0.0439(3) Uani 1 1 d . . . C3 C 0.32081(13) 0.8026(2) 0.33330(6) 0.0502(4) Uani 1 1 d . . . H2 H 0.3962 0.7679 0.3218 0.06 Uiso 1 1 calc R . . C4 C 0.29319(13) 0.7935(2) 0.38971(6) 0.0515(4) Uani 1 1 d . . . C5 C 0.17733(14) 0.8507(2) 0.40615(6) 0.0563(4) Uani 1 1 d . . . H4 H 0.1571 0.8485 0.4434 0.068 Uiso 1 1 calc R . . C6 C 0.09710(14) 0.9076(2) 0.36835(6) 0.0525(4) Uani 1 1 d . . . H5 H 0.022 0.9427 0.3802 0.063 Uiso 1 1 calc R . . C8 C -0.00366(12) 0.91896(19) 0.17163(6) 0.0466(4) Uani 1 1 d . . . C9 C 0.07616(13) 0.8702(2) 0.13008(6) 0.0477(4) Uani 1 1 d . . . C10 C 0.03322(14) 0.8187(2) 0.07931(6) 0.0560(4) Uani 1 1 d . . . H10 H 0.0845 0.7854 0.0512 0.067 Uiso 1 1 calc R . . C11 C -0.08977(15) 0.8185(2) 0.07175(7) 0.0607(4) Uani 1 1 d . . . C12 C -0.16887(15) 0.8663(2) 0.11204(7) 0.0637(5) Uani 1 1 d . . . H12 H -0.2508 0.8647 0.1048 0.076 Uiso 1 1 calc R . . C13 C -0.12600(13) 0.9169(2) 0.16345(7) 0.0567(4) Uani 1 1 d . . . H13 H -0.1779 0.9485 0.1915 0.068 Uiso 1 1 calc R . . C14 C 0.25259(12) 1.1525(2) 0.19686(6) 0.0476(4) Uani 1 1 d . . . C15 C 0.21454(14) 1.2613(2) 0.15426(8) 0.0620(5) Uani 1 1 d . . . H15 H 0.1598 1.2199 0.1282 0.074 Uiso 1 1 calc R . . C16 C 0.25516(18) 1.4274(3) 0.14951(10) 0.0809(6) Uani 1 1 d . . . H16 H 0.2267 1.4969 0.1209 0.097 Uiso 1 1 calc R . . C17 C 0.3366(2) 1.4909(3) 0.18641(10) 0.0851(7) Uani 1 1 d . . . H17 H 0.364 1.6035 0.183 0.102 Uiso 1 1 calc R . . C18 C 0.37873(19) 1.3877(3) 0.22896(9) 0.0804(6) Uani 1 1 d . . . H18 H 0.4353 1.4299 0.2541 0.097 Uiso 1 1 calc R . . C19 C 0.33598(15) 1.2197(2) 0.23408(7) 0.0613(4) Uani 1 1 d . . . H19 H 0.3639 1.1512 0.2631 0.074 Uiso 1 1 calc R . . C20 C 0.34042(17) 0.6951(3) 0.48473(7) 0.0701(5) Uani 1 1 d . . . H20A H 0.3856 0.5959 0.4976 0.084 Uiso 1 1 calc R . . H20B H 0.2561 0.6655 0.4858 0.084 Uiso 1 1 calc R . . C21 C 0.3633(3) 0.8422(3) 0.52328(9) 0.1029(8) Uani 1 1 d . . . H21A H 0.447 0.8705 0.5232 0.154 Uiso 1 1 calc R . . H21B H 0.3402 0.8102 0.56 0.154 Uiso 1 1 calc R . . H21C H 0.3174 0.9403 0.5114 0.154 Uiso 1 1 calc R . . C22 C 0.49449(14) 0.6818(3) 0.41188(7) 0.0695(5) Uani 1 1 d . . . H22A H 0.5473 0.6951 0.4438 0.083 Uiso 1 1 calc R . . H22B H 0.5222 0.759 0.3832 0.083 Uiso 1 1 calc R . . C23 C 0.50218(16) 0.4994(3) 0.39136(8) 0.0792(6) Uani 1 1 d . . . H23A H 0.4723 0.4226 0.4191 0.119 Uiso 1 1 calc R . . H23B H 0.5841 0.4716 0.3838 0.119 Uiso 1 1 calc R . . H23C H 0.455 0.4876 0.3581 0.119 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0368(8) 0.0519(10) 0.0455(9) 0.0032(7) 0.0085(6) 0.0051(7) N1 0.0384(6) 0.0491(7) 0.0484(7) 0.0043(5) 0.0073(5) 0.0037(5) N2 0.0551(8) 0.0804(11) 0.0490(8) 0.0150(7) 0.0035(6) 0.0040(7) N3 0.0744(11) 0.0862(13) 0.0785(11) -0.0078(9) -0.0242(9) 0.0030(9) O2 0.0427(5) 0.0536(7) 0.0468(6) 0.0074(4) 0.0098(4) 0.0089(4) O1 0.0414(5) 0.0603(7) 0.0493(6) -0.0018(5) 0.0058(4) 0.0048(4) O4 0.0959(12) 0.204(2) 0.0812(11) -0.0534(12) -0.0113(9) 0.0178(13) O3 0.0829(11) 0.1307(15) 0.1145(13) -0.0318(10) -0.0415(9) 0.0094(10) C7 0.0416(7) 0.0489(9) 0.0544(9) 0.0026(7) 0.0138(6) 0.0044(6) C1 0.0432(8) 0.0465(9) 0.0489(8) 0.0023(6) 0.0078(6) 0.0024(6) C2 0.0444(7) 0.0417(8) 0.0458(8) 0.0053(6) 0.0094(6) -0.0006(6) C3 0.0426(7) 0.0555(10) 0.0529(9) 0.0101(7) 0.0081(6) 0.0041(7) C4 0.0509(8) 0.0544(10) 0.0493(9) 0.0071(7) 0.0036(6) -0.0027(7) C5 0.0594(9) 0.0644(11) 0.0451(8) 0.0019(7) 0.0096(7) 0.0015(8) C6 0.0478(8) 0.0579(10) 0.0520(9) -0.0025(7) 0.0121(7) 0.0029(7) C8 0.0433(8) 0.0458(8) 0.0507(8) 0.0075(6) 0.0021(6) 0.0021(6) C9 0.0449(8) 0.0470(9) 0.0513(9) 0.0056(6) 0.0020(6) 0.0024(6) C10 0.0573(9) 0.0586(10) 0.0522(9) 0.0003(7) 0.0016(7) 0.0034(7) C11 0.0606(10) 0.0586(11) 0.0625(10) 0.0005(8) -0.0105(8) 0.0016(8) C12 0.0465(9) 0.0665(12) 0.0779(12) 0.0041(9) -0.0099(8) 0.0015(8) C13 0.0438(8) 0.0604(11) 0.0660(10) 0.0047(8) 0.0049(7) 0.0036(7) C14 0.0412(7) 0.0503(9) 0.0518(8) 0.0034(7) 0.0156(6) 0.0049(6) C15 0.0474(8) 0.0620(11) 0.0770(11) 0.0181(8) 0.0116(8) 0.0072(8) C16 0.0666(12) 0.0591(12) 0.1180(17) 0.0307(11) 0.0310(11) 0.0113(10) C17 0.0918(15) 0.0445(11) 0.1205(18) -0.0024(11) 0.0549(14) -0.0018(10) C18 0.0865(13) 0.0737(14) 0.0819(13) -0.0277(11) 0.0326(11) -0.0248(11) C19 0.0678(10) 0.0625(11) 0.0539(9) -0.0057(8) 0.0153(8) -0.0101(8) C20 0.0754(12) 0.0830(14) 0.0518(10) 0.0124(9) 0.0014(8) 0.0104(10) C21 0.144(2) 0.0902(18) 0.0741(14) -0.0023(12) -0.0097(13) 0.0256(15) C22 0.0471(9) 0.0992(16) 0.0622(10) 0.0270(10) -0.0024(7) -0.0005(9) C23 0.0601(11) 0.1031(17) 0.0748(12) 0.0253(11) 0.0132(9) 0.0197(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 B1 O2 1.4606(19) . ? B1 O1 1.494(2) . ? B1 N1 1.5867(18) . ? B1 C14 1.600(2) . ? N1 C7 1.3127(18) . ? N1 C8 1.3984(19) . ? N2 C4 1.353(2) . ? N2 C22 1.465(2) . ? N2 C20 1.465(2) . ? N3 O4 1.211(2) . ? N3 O3 1.2140(19) . ? N3 C11 1.470(2) . ? O2 C2 1.3416(16) . ? O1 C9 1.3443(17) . ? C7 C1 1.394(2) . ? C1 C6 1.410(2) . ? C1 C2 1.4322(19) . ? C2 C3 1.370(2) . ? C3 C4 1.404(2) . ? C4 C5 1.429(2) . ? C5 C6 1.346(2) . ? C8 C13 1.378(2) . ? C8 C9 1.403(2) . ? C9 C10 1.371(2) . ? C10 C11 1.383(2) . ? C11 C12 1.374(2) . ? C12 C13 1.383(2) . ? C14 C19 1.388(2) . ? C14 C15 1.393(2) . ? C15 C16 1.373(3) . ? C16 C17 1.358(3) . ? C17 C18 1.382(3) . ? C18 C19 1.395(3) . ? C20 C21 1.493(3) . ? C22 C23 1.503(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 O2 B1 O1 112.42(12) . . ? O2 B1 N1 107.28(11) . . ? O1 B1 N1 99.81(11) . . ? O2 B1 C14 112.40(13) . . ? O1 B1 C14 111.58(12) . . ? N1 B1 C14 112.64(12) . . ? C7 N1 C8 128.69(12) . . ? C7 N1 B1 121.39(12) . . ? C8 N1 B1 107.88(11) . . ? C4 N2 C22 121.73(13) . . ? C4 N2 C20 122.42(13) . . ? C22 N2 C20 115.63(13) . . ? O4 N3 O3 122.94(18) . . ? O4 N3 C11 118.57(16) . . ? O3 N3 C11 118.45(18) . . ? C2 O2 B1 119.29(11) . . ? C9 O1 B1 109.18(11) . . ? N1 C7 C1 119.48(13) . . ? C7 C1 C6 122.66(13) . . ? C7 C1 C2 119.17(13) . . ? C6 C1 C2 117.19(13) . . ? O2 C2 C3 118.41(12) . . ? O2 C2 C1 121.07(13) . . ? C3 C2 C1 120.39(13) . . ? C2 C3 C4 121.61(13) . . ? N2 C4 C3 121.34(14) . . ? N2 C4 C5 120.91(13) . . ? C3 C4 C5 117.74(14) . . ? C6 C5 C4 120.69(14) . . ? C5 C6 C1 122.36(14) . . ? C13 C8 N1 130.87(14) . . ? C13 C8 C9 122.13(14) . . ? N1 C8 C9 106.90(12) . . ? O1 C9 C10 126.02(13) . . ? O1 C9 C8 113.90(13) . . ? C10 C9 C8 120.07(14) . . ? C9 C10 C11 116.99(15) . . ? C12 C11 C10 123.51(16) . . ? C12 C11 N3 118.45(16) . . ? C10 C11 N3 118.03(16) . . ? C11 C12 C13 119.69(15) . . ? C8 C13 C12 117.61(15) . . ? C19 C14 C15 116.56(16) . . ? C19 C14 B1 122.84(14) . . ? C15 C14 B1 120.60(15) . . ? C16 C15 C14 122.20(19) . . ? C17 C16 C15 120.4(2) . . ? C16 C17 C18 119.78(19) . . ? C17 C18 C19 119.7(2) . . ? C14 C19 C18 121.41(19) . . ? N2 C20 C21 113.63(18) . . ? N2 C22 C23 112.91(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 B1 N1 C7 32.92(18) . . . . ? O1 B1 N1 C7 150.25(13) . . . . ? C14 B1 N1 C7 -91.29(16) . . . . ? O2 B1 N1 C8 -132.16(13) . . . . ? O1 B1 N1 C8 -14.83(14) . . . . ? C14 B1 N1 C8 103.63(14) . . . . ? O1 B1 O2 C2 -147.15(12) . . . . ? N1 B1 O2 C2 -38.41(17) . . . . ? C14 B1 O2 C2 85.95(15) . . . . ? O2 B1 O1 C9 127.12(12) . . . . ? N1 B1 O1 C9 13.69(14) . . . . ? C14 B1 O1 C9 -105.55(13) . . . . ? C8 N1 C7 C1 153.34(15) . . . . ? B1 N1 C7 C1 -8.4(2) . . . . ? N1 C7 C1 C6 178.37(14) . . . . ? N1 C7 C1 C2 -13.3(2) . . . . ? B1 O2 C2 C3 -162.44(14) . . . . ? B1 O2 C2 C1 21.7(2) . . . . ? C7 C1 C2 O2 7.4(2) . . . . ? C6 C1 C2 O2 176.36(14) . . . . ? C7 C1 C2 C3 -168.43(15) . . . . ? C6 C1 C2 C3 0.5(2) . . . . ? O2 C2 C3 C4 -175.78(14) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C22 N2 C4 C3 4.2(3) . . . . ? C20 N2 C4 C3 -170.12(16) . . . . ? C22 N2 C4 C5 -176.33(17) . . . . ? C20 N2 C4 C5 9.3(3) . . . . ? C2 C3 C4 N2 178.36(15) . . . . ? C2 C3 C4 C5 -1.1(2) . . . . ? N2 C4 C5 C6 -178.06(16) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? C7 C1 C6 C5 168.32(16) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C7 N1 C8 C13 23.5(3) . . . . ? B1 N1 C8 C13 -172.87(16) . . . . ? C7 N1 C8 C9 -152.86(14) . . . . ? B1 N1 C8 C9 10.79(15) . . . . ? B1 O1 C9 C10 172.83(15) . . . . ? B1 O1 C9 C8 -8.58(17) . . . . ? C13 C8 C9 O1 -178.58(14) . . . . ? N1 C8 C9 O1 -1.85(17) . . . . ? C13 C8 C9 C10 0.1(2) . . . . ? N1 C8 C9 C10 176.84(13) . . . . ? O1 C9 C10 C11 178.79(15) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C9 C10 C11 N3 -178.95(15) . . . . ? O4 N3 C11 C12 -173.3(2) . . . . ? O3 N3 C11 C12 4.4(3) . . . . ? O4 N3 C11 C10 5.6(3) . . . . ? O3 N3 C11 C10 -176.70(19) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? N3 C11 C12 C13 178.40(16) . . . . ? N1 C8 C13 C12 -176.52(16) . . . . ? C9 C8 C13 C12 -0.6(2) . . . . ? C11 C12 C13 C8 0.8(3) . . . . ? O2 B1 C14 C19 -11.32(19) . . . . ? O1 B1 C14 C19 -138.67(13) . . . . ? N1 B1 C14 C19 110.02(15) . . . . ? O2 B1 C14 C15 168.33(12) . . . . ? O1 B1 C14 C15 40.98(18) . . . . ? N1 B1 C14 C15 -70.34(17) . . . . ? C19 C14 C15 C16 -1.1(2) . . . . ? B1 C14 C15 C16 179.20(15) . . . . ? C14 C15 C16 C17 1.1(3) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C15 C14 C19 C18 0.2(2) . . . . ? B1 C14 C19 C18 179.89(14) . . . . ? C17 C18 C19 C14 0.7(3) . . . . ? C4 N2 C20 C21 -92.9(2) . . . . ? C22 N2 C20 C21 92.5(2) . . . . ? C4 N2 C22 C23 -86.2(2) . . . . ? C20 N2 C22 C23 88.49(19) . . . . ? data_nfvb23 _database_code_CSD 175922 _audit_creation_date 2002-07-05T10:46:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-(4-fluorophenyl)-(3¥-nitrobenzo[d])-(4¥¥-diethylaminobenzo[h])-1,3- dioxa-6-aza-2-boracyclonon-6-ene ; _chemical_formula_moiety 'C23 H21 B1 F1 N3 O4' _chemical_formula_structural 'C23 H21 B1 F1 N3 O4' _chemical_formula_sum 'C23 H21 B F N3 O4' _chemical_formula_weight 433.24 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.229 _cell_length_b 15.668 _cell_length_c 12.587 _cell_angle_alpha 90 _cell_angle_beta 108.23 _cell_angle_gamma 90 _cell_volume 2103.4 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5600 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.1 _exptl_absorpt_factor_muR 0.035 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; ? ; _exptl_absorpt_correction_T_min 0.6497 _exptl_absorpt_correction_T_max 0.8978 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.5057E-2 _diffrn_orient_matrix_ub_12 0.17988E-1 _diffrn_orient_matrix_ub_13 -0.77656E-1 _diffrn_orient_matrix_ub_21 0.07104 _diffrn_orient_matrix_ub_22 0.40725E-1 _diffrn_orient_matrix_ub_23 0.31293E-1 _diffrn_orient_matrix_ub_31 0.06103 _diffrn_orient_matrix_ub_32 -0.45735E-1 _diffrn_orient_matrix_ub_33 -0.2555E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.037 _diffrn_standards_decay_corr_min 0.968 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 8 0 -7 3 -4 3 0 8 2 _diffrn_reflns_av_unetI/netI 0.0665 _diffrn_reflns_number 4460 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4237 _reflns_number_gt 1949 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0766P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_coef 0.0005(12) _refine_ls_number_reflns 4237 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1578 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.185 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' F F 0.0171 0.0103 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 H7 H 0.334(2) 0.3169(17) 0.469(2) 0.045(8) Uiso 1 1 d . . . H2 H -0.010(3) 0.2640(17) 0.666(2) 0.046(8) Uiso 1 1 d . . . H19 H 0.074(3) 0.045(2) 0.606(3) 0.082(11) Uiso 1 1 d . . . H15 H 0.374(3) 0.0768(19) 0.499(2) 0.058(9) Uiso 1 1 d . . . H5 H 0.357(3) 0.398(2) 0.639(3) 0.085(11) Uiso 1 1 d . . . H12 H 0.337(3) 0.205(2) 0.107(3) 0.088(12) Uiso 1 1 d . . . H10 H 0.031(3) 0.079(2) 0.138(2) 0.062(10) Uiso 1 1 d . . . H4 H 0.263(3) 0.435(2) 0.776(3) 0.072(11) Uiso 1 1 d . . . H18 H 0.182(3) -0.063(2) 0.728(3) 0.091(12) Uiso 1 1 d . . . H20A H 0.055(3) 0.470(2) 0.931(3) 0.090(12) Uiso 1 1 d . . . H13 H 0.378(3) 0.2553(19) 0.290(2) 0.052(9) Uiso 1 1 d . . . H22B H -0.096(3) 0.393(2) 0.849(3) 0.069(10) Uiso 1 1 d . . . H23B H -0.138(4) 0.249(3) 0.876(3) 0.125(17) Uiso 1 1 d . . . H16 H 0.484(4) -0.038(3) 0.615(3) 0.097(12) Uiso 1 1 d . . . H22A H -0.119(4) 0.331(2) 0.740(3) 0.099(13) Uiso 1 1 d . . . H20B H 0.154(3) 0.494(3) 0.865(3) 0.092(12) Uiso 1 1 d . . . H23A H -0.001(4) 0.219(3) 0.855(3) 0.105(14) Uiso 1 1 d . . . H23C H -0.002(3) 0.286(2) 0.960(3) 0.067(10) Uiso 1 1 d . . . O2 O 0.06398(16) 0.20087(13) 0.51248(16) 0.0530(5) Uani 1 1 d . . . O1 O 0.06716(17) 0.12074(14) 0.34648(16) 0.0561(6) Uani 1 1 d . . . N1 N 0.2339(2) 0.21506(16) 0.42856(19) 0.0475(6) Uani 1 1 d . . . C4 C 0.1184(3) 0.35636(19) 0.7392(2) 0.0502(7) Uani 1 1 d . . . C1 C 0.2319(2) 0.30352(19) 0.5780(2) 0.0462(7) Uani 1 1 d . . . C3 C 0.0674(3) 0.2891(2) 0.6640(2) 0.0505(8) Uani 1 1 d . . . N2 N 0.0626(2) 0.38247(16) 0.8140(2) 0.0577(7) Uani 1 1 d . . . C2 C 0.1217(2) 0.26265(19) 0.5862(2) 0.0473(7) Uani 1 1 d . . . C14 C 0.2156(3) 0.07590(19) 0.5402(2) 0.0475(7) Uani 1 1 d . . . C7 C 0.2770(3) 0.2836(2) 0.4899(3) 0.0492(8) Uani 1 1 d . . . F1 F 0.4006(2) -0.11833(14) 0.7500(2) 0.1028(8) Uani 1 1 d . . . C19 C 0.1611(3) 0.0327(2) 0.6097(3) 0.0605(9) Uani 1 1 d . . . C9 C 0.1310(3) 0.1400(2) 0.2755(2) 0.0507(7) Uani 1 1 d . . . C6 C 0.2803(3) 0.3718(2) 0.6527(3) 0.0560(8) Uani 1 1 d . . . C10 C 0.1038(3) 0.1118(2) 0.1669(3) 0.0555(8) Uani 1 1 d . . . C11 C 0.1810(3) 0.1399(2) 0.1083(2) 0.0586(8) Uani 1 1 d . . . C5 C 0.2280(3) 0.3964(2) 0.7302(3) 0.0584(9) Uani 1 1 d . . . C8 C 0.2347(3) 0.19500(19) 0.3206(2) 0.0491(7) Uani 1 1 d . . . C13 C 0.3107(3) 0.2209(2) 0.2611(3) 0.0570(8) Uani 1 1 d . . . C15 C 0.3340(3) 0.0490(2) 0.5443(3) 0.0569(8) Uani 1 1 d . . . C16 C 0.3977(4) -0.0164(2) 0.6141(3) 0.0661(9) Uani 1 1 d . . . C20 C 0.1204(4) 0.4463(3) 0.9001(3) 0.0741(11) Uani 1 1 d . . . N3 N 0.1549(4) 0.1107(2) -0.0084(2) 0.0732(8) Uani 1 1 d . . . B1 B 0.1423(3) 0.1521(2) 0.4607(3) 0.0492(8) Uani 1 1 d . . . C18 C 0.2224(4) -0.0333(2) 0.6803(3) 0.0705(10) Uani 1 1 d . . . C17 C 0.3397(3) -0.0547(2) 0.6806(3) 0.0657(9) Uani 1 1 d . . . O3 O 0.2263(3) 0.1296(2) -0.0588(2) 0.1128(11) Uani 1 1 d . . . C22 C -0.0587(3) 0.3478(2) 0.8150(3) 0.0635(9) Uani 1 1 d . . . O4 O 0.0582(3) 0.07077(19) -0.0506(2) 0.0927(9) Uani 1 1 d . . . C12 C 0.2850(4) 0.1916(2) 0.1523(3) 0.0649(9) Uani 1 1 d . . . C23 C -0.0476(5) 0.2693(3) 0.8837(4) 0.0869(12) Uani 1 1 d . . . C21 C 0.2188(5) 0.4092(3) 0.9988(4) 0.1218(18) Uani 1 1 d . . . H21A H 0.2534 0.4534 1.0523 0.183 Uiso 1 1 calc R . . H21B H 0.2841 0.3843 0.9746 0.183 Uiso 1 1 calc R . . H21C H 0.1819 0.366 1.0327 0.183 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0366(10) 0.0638(13) 0.0611(12) -0.0128(11) 0.0189(9) -0.0082(10) O1 0.0431(11) 0.0755(15) 0.0490(11) -0.0087(10) 0.0133(9) -0.0108(10) N1 0.0362(12) 0.0579(16) 0.0493(14) -0.0015(12) 0.0145(11) -0.0013(12) C4 0.0482(17) 0.0504(17) 0.0493(17) 0.0004(15) 0.0113(14) 0.0034(15) C1 0.0368(15) 0.0486(17) 0.0511(16) 0.0004(14) 0.0106(13) -0.0010(13) C3 0.0390(16) 0.0589(19) 0.0532(18) -0.0055(15) 0.0140(14) -0.0011(15) N2 0.0622(16) 0.0589(16) 0.0532(15) -0.0089(13) 0.0196(13) -0.0023(13) C2 0.0356(15) 0.0480(17) 0.0517(16) -0.0029(14) 0.0040(13) -0.0009(13) C14 0.0432(16) 0.0545(17) 0.0456(16) -0.0144(14) 0.0151(13) -0.0091(14) C7 0.0341(16) 0.0545(19) 0.0570(18) 0.0102(16) 0.0114(14) -0.0009(14) F1 0.1037(17) 0.0756(15) 0.1169(19) 0.0283(13) 0.0169(14) 0.0069(13) C19 0.0509(19) 0.068(2) 0.064(2) -0.0007(18) 0.0204(17) -0.0068(18) C9 0.0425(16) 0.066(2) 0.0458(17) 0.0045(15) 0.0166(13) 0.0085(15) C6 0.0469(18) 0.054(2) 0.064(2) 0.0020(16) 0.0130(16) -0.0077(16) C10 0.0547(19) 0.058(2) 0.0532(19) 0.0042(16) 0.0156(16) 0.0079(17) C11 0.069(2) 0.0582(19) 0.0512(18) 0.0048(16) 0.0230(17) 0.0132(18) C5 0.059(2) 0.054(2) 0.058(2) -0.0075(17) 0.0125(17) -0.0084(17) C8 0.0423(16) 0.0553(18) 0.0508(17) 0.0049(15) 0.0164(14) 0.0047(14) C13 0.052(2) 0.0551(19) 0.069(2) 0.0021(17) 0.0258(17) 0.0007(17) C15 0.056(2) 0.058(2) 0.062(2) -0.0062(17) 0.0262(17) -0.0051(16) C16 0.062(2) 0.057(2) 0.079(2) -0.0053(19) 0.021(2) 0.0062(18) C20 0.088(3) 0.070(3) 0.067(2) -0.018(2) 0.027(2) -0.007(2) N3 0.095(2) 0.071(2) 0.0593(19) 0.0053(16) 0.0327(19) 0.0135(19) B1 0.0366(17) 0.060(2) 0.0511(19) -0.0083(17) 0.0144(15) -0.0116(16) C18 0.073(2) 0.068(2) 0.071(2) 0.005(2) 0.024(2) -0.017(2) C17 0.070(2) 0.049(2) 0.069(2) 0.0020(17) 0.0079(19) -0.0058(18) O3 0.138(3) 0.147(3) 0.0771(18) -0.0080(18) 0.067(2) -0.008(2) C22 0.069(2) 0.067(2) 0.058(2) -0.0028(19) 0.0260(19) 0.0091(19) O4 0.124(2) 0.092(2) 0.0601(16) -0.0089(14) 0.0259(16) -0.0138(19) C12 0.075(2) 0.068(2) 0.064(2) 0.0107(19) 0.039(2) 0.0111(19) C23 0.103(4) 0.076(3) 0.077(3) 0.007(2) 0.022(3) -0.001(3) C21 0.151(5) 0.111(4) 0.071(3) -0.005(2) -0.011(3) -0.038(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 C2 1.357(3) . ? O2 B1 1.463(4) . ? O1 C9 1.343(3) . ? O1 B1 1.504(4) . ? N1 C7 1.324(4) . ? N1 C8 1.397(3) . ? N1 B1 1.566(4) . ? C4 N2 1.347(3) . ? C4 C3 1.412(4) . ? C4 C5 1.417(4) . ? C1 C7 1.390(4) . ? C1 C6 1.417(4) . ? C1 C2 1.426(4) . ? C3 C2 1.370(4) . ? N2 C20 1.468(4) . ? N2 C22 1.470(4) . ? C14 C15 1.380(4) . ? C14 C19 1.391(4) . ? C14 B1 1.609(5) . ? F1 C17 1.360(4) . ? C19 C18 1.397(5) . ? C9 C10 1.376(4) . ? C9 C8 1.416(4) . ? C6 C5 1.342(4) . ? C10 C11 1.375(4) . ? C11 C12 1.387(5) . ? C11 N3 1.477(4) . ? C8 C13 1.362(4) . ? C13 C12 1.386(5) . ? C15 C16 1.392(5) . ? C16 C17 1.353(5) . ? C20 C21 1.498(6) . ? N3 O3 1.205(4) . ? N3 O4 1.221(4) . ? C18 C17 1.358(5) . ? C22 C23 1.486(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 C2 O2 B1 116.9(2) . . ? C9 O1 B1 107.8(2) . . ? C7 N1 C8 129.6(3) . . ? C7 N1 B1 120.7(2) . . ? C8 N1 B1 108.3(2) . . ? N2 C4 C3 121.0(3) . . ? N2 C4 C5 121.8(3) . . ? C3 C4 C5 117.1(3) . . ? C7 C1 C6 122.6(3) . . ? C7 C1 C2 119.9(3) . . ? C6 C1 C2 116.9(3) . . ? C2 C3 C4 121.8(3) . . ? C4 N2 C20 121.9(3) . . ? C4 N2 C22 121.9(3) . . ? C20 N2 C22 116.2(3) . . ? O2 C2 C3 118.7(3) . . ? O2 C2 C1 120.7(3) . . ? C3 C2 C1 120.4(3) . . ? C15 C14 C19 115.8(3) . . ? C15 C14 B1 123.3(3) . . ? C19 C14 B1 120.9(3) . . ? N1 C7 C1 119.3(3) . . ? C14 C19 C18 122.3(3) . . ? O1 C9 C10 126.1(3) . . ? O1 C9 C8 114.4(3) . . ? C10 C9 C8 119.5(3) . . ? C5 C6 C1 122.3(3) . . ? C9 C10 C11 116.7(3) . . ? C10 C11 C12 124.4(3) . . ? C10 C11 N3 118.2(3) . . ? C12 C11 N3 117.3(3) . . ? C6 C5 C4 121.3(3) . . ? C13 C8 N1 131.6(3) . . ? C13 C8 C9 122.6(3) . . ? N1 C8 C9 105.8(2) . . ? C8 C13 C12 118.2(3) . . ? C14 C15 C16 123.2(3) . . ? C17 C16 C15 117.7(3) . . ? N2 C20 C21 112.9(3) . . ? O3 N3 O4 123.0(3) . . ? O3 N3 C11 119.3(4) . . ? O4 N3 C11 117.7(3) . . ? O2 B1 O1 111.2(2) . . ? O2 B1 N1 108.7(3) . . ? O1 B1 N1 100.2(2) . . ? O2 B1 C14 111.8(2) . . ? O1 B1 C14 112.1(3) . . ? N1 B1 C14 112.2(2) . . ? C17 C18 C19 118.0(3) . . ? C16 C17 C18 122.9(3) . . ? C16 C17 F1 118.7(3) . . ? C18 C17 F1 118.4(3) . . ? N2 C22 C23 113.6(3) . . ? C11 C12 C13 118.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C4 C3 C2 178.9(3) . . . . ? C5 C4 C3 C2 0.6(4) . . . . ? C3 C4 N2 C20 173.8(3) . . . . ? C5 C4 N2 C20 -8.0(5) . . . . ? C3 C4 N2 C22 -5.3(4) . . . . ? C5 C4 N2 C22 172.9(3) . . . . ? B1 O2 C2 C3 -157.6(3) . . . . ? B1 O2 C2 C1 26.7(4) . . . . ? C4 C3 C2 O2 -176.4(3) . . . . ? C4 C3 C2 C1 -0.7(4) . . . . ? C7 C1 C2 O2 3.8(4) . . . . ? C6 C1 C2 O2 175.2(3) . . . . ? C7 C1 C2 C3 -171.8(3) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? C8 N1 C7 C1 159.3(3) . . . . ? B1 N1 C7 C1 -5.5(4) . . . . ? C6 C1 C7 N1 175.0(3) . . . . ? C2 C1 C7 N1 -14.2(4) . . . . ? C15 C14 C19 C18 0.5(5) . . . . ? B1 C14 C19 C18 -179.6(3) . . . . ? B1 O1 C9 C10 170.1(3) . . . . ? B1 O1 C9 C8 -10.2(3) . . . . ? C7 C1 C6 C5 172.9(3) . . . . ? C2 C1 C6 C5 1.7(4) . . . . ? O1 C9 C10 C11 179.6(3) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 2.2(5) . . . . ? C9 C10 C11 N3 179.8(3) . . . . ? C1 C6 C5 C4 -1.9(5) . . . . ? N2 C4 C5 C6 -177.6(3) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C7 N1 C8 C13 25.1(5) . . . . ? B1 N1 C8 C13 -168.7(3) . . . . ? C7 N1 C8 C9 -152.7(3) . . . . ? B1 N1 C8 C9 13.5(3) . . . . ? O1 C9 C8 C13 179.5(3) . . . . ? C10 C9 C8 C13 -0.7(4) . . . . ? O1 C9 C8 N1 -2.4(3) . . . . ? C10 C9 C8 N1 177.3(3) . . . . ? N1 C8 C13 C12 -177.8(3) . . . . ? C9 C8 C13 C12 -0.4(4) . . . . ? C19 C14 C15 C16 -0.8(5) . . . . ? B1 C14 C15 C16 179.3(3) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C4 N2 C20 C21 -80.6(5) . . . . ? C22 N2 C20 C21 98.6(4) . . . . ? C10 C11 N3 O3 -174.9(3) . . . . ? C12 C11 N3 O3 3.0(5) . . . . ? C10 C11 N3 O4 7.8(5) . . . . ? C12 C11 N3 O4 -174.4(3) . . . . ? C2 O2 B1 O1 -151.2(2) . . . . ? C2 O2 B1 N1 -41.8(3) . . . . ? C2 O2 B1 C14 82.7(3) . . . . ? C9 O1 B1 O2 131.5(3) . . . . ? C9 O1 B1 N1 16.7(3) . . . . ? C9 O1 B1 C14 -102.5(3) . . . . ? C7 N1 B1 O2 32.5(3) . . . . ? C8 N1 B1 O2 -135.2(2) . . . . ? C7 N1 B1 O1 149.2(2) . . . . ? C8 N1 B1 O1 -18.5(3) . . . . ? C7 N1 B1 C14 -91.7(3) . . . . ? C8 N1 B1 C14 100.6(3) . . . . ? C15 C14 B1 O2 -146.2(3) . . . . ? C19 C14 B1 O2 33.9(4) . . . . ? C15 C14 B1 O1 88.2(3) . . . . ? C19 C14 B1 O1 -91.7(3) . . . . ? C15 C14 B1 N1 -23.6(4) . . . . ? C19 C14 B1 N1 156.4(3) . . . . ? C14 C19 C18 C17 0.6(5) . . . . ? C15 C16 C17 C18 1.3(5) . . . . ? C15 C16 C17 F1 -179.5(3) . . . . ? C19 C18 C17 C16 -1.6(5) . . . . ? C19 C18 C17 F1 179.3(3) . . . . ? C4 N2 C22 C23 87.8(4) . . . . ? C20 N2 C22 C23 -91.4(4) . . . . ? C10 C11 C12 C13 -3.3(5) . . . . ? N3 C11 C12 C13 179.0(3) . . . . ? C8 C13 C12 C11 2.2(5) . . . . ? data_rsvb16 _database_code_CSD 175923 _audit_creation_date 2002-07-05T10:59:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-(4-Bromophenyl)-(3¥-nitrobenzo[d])-(4¥¥-diethylaminobenzo[h])-1,3- dioxa-6-aza-2-boracyclonon-6-ene' ' ; _chemical_formula_moiety 'C23 H21 B1 Br1 N3 O4' _chemical_formula_structural 'C23 H21 B1 Br1 N3 O4' _chemical_formula_sum 'C23 H21 B Br N3 O4' _chemical_formula_weight 494.15 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.27(3) _cell_length_b 16.565(9) _cell_length_c 12.270(12) _cell_angle_alpha 90.00(6) _cell_angle_beta 107.45(4) _cell_angle_gamma 90.00(9) _cell_volume 2185(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description cubic _exptl_crystal_colour red _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.48 _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.917 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.02638 _diffrn_orient_matrix_ub_12 0.52495E-1 _diffrn_orient_matrix_ub_13 0.40238E-1 _diffrn_orient_matrix_ub_21 0.78E-4 _diffrn_orient_matrix_ub_22 0.25526E-1 _diffrn_orient_matrix_ub_23 -0.73902E-1 _diffrn_orient_matrix_ub_31 -0.89239E-1 _diffrn_orient_matrix_ub_32 0.01543 _diffrn_orient_matrix_ub_33 -0.14792E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.111 _diffrn_standards_decay_corr_min 0.941 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 5 -4 -3 4 -3 -2 -8 -1 _diffrn_reflns_av_unetI/netI 0.1076 _diffrn_reflns_number 4050 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3843 _reflns_number_gt 1759 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0806P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3843 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1605 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.515 _refine_diff_density_min -0.751 _refine_diff_density_rms 0.081 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Br Br -0.2901 2.4595 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Br1 Br 0.08213(6) 0.10892(4) 0.22713(6) 0.0675(3) Uani 1 1 d . . . O1 O 0.4434(3) -0.1300(2) 0.6782(3) 0.0430(9) Uani 1 1 d . . . O2 O 0.4432(3) -0.2112(2) 0.5110(3) 0.0395(8) Uani 1 1 d . . . N3 N 0.3543(5) -0.1049(3) 1.0408(4) 0.0582(13) Uani 1 1 d . . . N2 N 0.4246(4) -0.3822(2) 0.1952(4) 0.0435(10) Uani 1 1 d . . . O4 O 0.4501(4) -0.0678(3) 1.0811(3) 0.0684(11) Uani 1 1 d . . . C1 C 0.2692(4) -0.3037(3) 0.4468(4) 0.0368(12) Uani 1 1 d . . . C6 C 0.2157(5) -0.3658(3) 0.3704(5) 0.0461(14) Uani 1 1 d . . . C7 C 0.2289(5) -0.2817(3) 0.5407(5) 0.0398(13) Uani 1 1 d . . . O3 O 0.2806(5) -0.1179(3) 1.0924(4) 0.1027(19) Uani 1 1 d . . . N1 N 0.2757(3) -0.2195(2) 0.6015(3) 0.0346(9) Uani 1 1 d . . . C19 C 0.3476(5) -0.0525(4) 0.4053(5) 0.0510(14) Uani 1 1 d . . . C14 C 0.2958(4) -0.0907(3) 0.4813(4) 0.0384(12) Uani 1 1 d . . . C20 C 0.3589(6) -0.4373(4) 0.1053(5) 0.0529(15) Uani 1 1 d . . . C15 C 0.1771(5) -0.0638(3) 0.4801(5) 0.0434(13) Uani 1 1 d . . . C22 C 0.5449(5) -0.3511(4) 0.1897(6) 0.0481(14) Uani 1 1 d . . . C5 C 0.2639(5) -0.3909(4) 0.2882(5) 0.0472(14) Uani 1 1 d . . . C10 C 0.4058(5) -0.1138(3) 0.8608(4) 0.0424(12) Uani 1 1 d . . . C16 C 0.1168(5) -0.0036(3) 0.4073(5) 0.0476(15) Uani 1 1 d . . . C11 C 0.3265(5) -0.1375(3) 0.9241(4) 0.0423(13) Uani 1 1 d . . . C9 C 0.3775(4) -0.1442(3) 0.7521(4) 0.0404(12) Uani 1 1 d . . . C8 C 0.2776(4) -0.1966(3) 0.7109(4) 0.0391(12) Uani 1 1 d . . . C13 C 0.2021(5) -0.2207(4) 0.7766(5) 0.0430(13) Uani 1 1 d . . . C18 C 0.2881(5) 0.0069(4) 0.3325(5) 0.0541(15) Uani 1 1 d . . . C12 C 0.2291(5) -0.1880(3) 0.8846(5) 0.0488(14) Uani 1 1 d . . . C23 C 0.5368(7) -0.2755(4) 0.1224(7) 0.0669(18) Uani 1 1 d . . . C3 C 0.4316(5) -0.2955(3) 0.3553(4) 0.0404(13) Uani 1 1 d . . . C4 C 0.3755(4) -0.3550(3) 0.2768(4) 0.0394(12) Uani 1 1 d . . . C17 C 0.1704(5) 0.0306(3) 0.3325(4) 0.0428(13) Uani 1 1 d . . . C21 C 0.2512(7) -0.3989(5) 0.0163(6) 0.0647(17) Uani 1 1 d . . . C2 C 0.3820(4) -0.2682(3) 0.4373(4) 0.0361(12) Uani 1 1 d . . . B1 B 0.3678(5) -0.1613(4) 0.5645(5) 0.0403(15) Uani 1 1 d . . . H33 H 0.471(3) -0.075(2) 0.890(3) 0.012(9) Uiso 1 1 d . . . H201 H 0.345(4) -0.488(3) 0.138(4) 0.037(13) Uiso 1 1 d . . . H232 H 0.502(6) -0.231(4) 0.147(5) 0.08(2) Uiso 1 1 d . . . H222 H 0.578(5) -0.398(3) 0.155(4) 0.053(15) Uiso 1 1 d . . . H212 H 0.210(5) -0.435(3) -0.048(5) 0.059(16) Uiso 1 1 d . . . H41 H 0.494(4) -0.267(2) 0.352(3) 0.025(12) Uiso 1 1 d . . . H11 H 0.174(4) -0.312(3) 0.554(3) 0.025(13) Uiso 1 1 d . . . H181 H 0.317(5) 0.033(3) 0.283(4) 0.053(17) Uiso 1 1 d . . . H61 H 0.233(4) -0.432(3) 0.244(4) 0.032(13) Uiso 1 1 d . . . H221 H 0.599(4) -0.350(3) 0.260(4) 0.032(14) Uiso 1 1 d . . . H202 H 0.419(5) -0.463(3) 0.069(4) 0.052(15) Uiso 1 1 d . . . H161 H 0.044(5) 0.014(3) 0.403(4) 0.045(15) Uiso 1 1 d . . . H151 H 0.138(5) -0.090(3) 0.530(4) 0.057(17) Uiso 1 1 d . . . H121 H 0.175(5) -0.200(3) 0.932(4) 0.056(16) Uiso 1 1 d . . . H231 H 0.479(6) -0.288(4) 0.037(5) 0.08(2) Uiso 1 1 d . . . H71 H 0.152(5) -0.394(3) 0.385(4) 0.054(16) Uiso 1 1 d . . . H131 H 0.148(5) -0.253(3) 0.744(4) 0.055(18) Uiso 1 1 d . . . H211 H 0.285(8) -0.351(5) -0.013(6) 0.12(3) Uiso 1 1 d . . . H191 H 0.431(6) -0.073(4) 0.403(5) 0.09(2) Uiso 1 1 d . . . H213 H 0.176(7) -0.380(4) 0.043(6) 0.10(2) Uiso 1 1 d . . . H233 H 0.624(6) -0.250(4) 0.126(5) 0.09(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0679(4) 0.0518(4) 0.0715(4) 0.0118(3) 0.0036(3) 0.0006(3) O1 0.0239(17) 0.064(2) 0.042(2) 0.0002(17) 0.0119(16) -0.0088(16) O2 0.0199(16) 0.049(2) 0.052(2) -0.0045(17) 0.0148(16) -0.0002(15) N3 0.064(3) 0.060(3) 0.053(3) -0.006(3) 0.022(3) 0.002(3) N2 0.033(2) 0.052(3) 0.046(3) -0.005(2) 0.013(2) 0.002(2) O4 0.077(3) 0.074(3) 0.054(2) -0.008(2) 0.020(2) -0.009(3) C1 0.024(2) 0.045(3) 0.043(3) 0.005(2) 0.012(2) 0.001(2) C6 0.035(3) 0.048(3) 0.054(4) 0.003(3) 0.011(3) -0.006(3) C7 0.019(3) 0.045(3) 0.053(4) 0.007(3) 0.006(3) -0.001(2) O3 0.100(4) 0.152(5) 0.080(3) -0.036(3) 0.063(3) -0.034(4) N1 0.020(2) 0.045(2) 0.039(2) 0.002(2) 0.0091(18) -0.0023(18) C19 0.031(3) 0.062(4) 0.065(4) 0.011(3) 0.022(3) -0.001(3) C14 0.030(3) 0.048(3) 0.040(3) -0.006(2) 0.014(2) -0.006(2) C20 0.058(4) 0.048(4) 0.057(4) -0.004(3) 0.023(3) 0.009(3) C15 0.038(3) 0.047(3) 0.051(3) 0.003(3) 0.023(3) 0.003(3) C22 0.039(3) 0.061(4) 0.050(4) 0.007(3) 0.022(3) 0.013(3) C5 0.044(3) 0.048(3) 0.048(3) -0.007(3) 0.011(3) -0.007(3) C10 0.033(3) 0.043(3) 0.049(3) 0.004(3) 0.008(3) 0.002(3) C16 0.036(3) 0.050(3) 0.059(4) -0.001(3) 0.018(3) 0.006(3) C11 0.037(3) 0.048(3) 0.044(3) 0.003(2) 0.015(3) 0.011(3) C9 0.026(3) 0.047(3) 0.048(3) 0.005(2) 0.012(3) 0.003(2) C8 0.032(3) 0.043(3) 0.040(3) 0.005(2) 0.007(2) 0.005(2) C13 0.032(3) 0.051(3) 0.050(4) 0.002(3) 0.019(3) 0.004(3) C18 0.051(4) 0.059(4) 0.057(4) 0.014(3) 0.024(3) -0.007(3) C12 0.040(3) 0.057(4) 0.060(4) 0.011(3) 0.031(3) 0.004(3) C23 0.069(5) 0.060(4) 0.075(5) 0.011(4) 0.026(4) -0.001(4) C3 0.024(3) 0.048(3) 0.052(3) 0.005(3) 0.014(3) -0.001(3) C4 0.026(3) 0.045(3) 0.047(3) 0.005(3) 0.011(2) 0.005(2) C17 0.046(3) 0.040(3) 0.042(3) 0.001(2) 0.011(3) 0.001(2) C21 0.055(4) 0.071(5) 0.061(4) -0.009(4) 0.007(4) -0.001(4) C2 0.024(3) 0.044(3) 0.042(3) 0.001(2) 0.012(2) 0.004(2) B1 0.023(3) 0.052(4) 0.046(4) 0.000(3) 0.010(3) -0.003(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br1 C17 1.890(5) . ? O1 C9 1.354(6) . ? O1 B1 1.493(7) . ? O2 C2 1.346(6) . ? O2 B1 1.474(7) . ? N3 O3 1.205(7) . ? N3 O4 1.212(7) . ? N3 C11 1.474(7) . ? N2 C4 1.358(6) . ? N2 C20 1.451(7) . ? N2 C22 1.471(8) . ? C1 C6 1.400(7) . ? C1 C7 1.407(7) . ? C1 C2 1.437(7) . ? C6 C5 1.348(8) . ? C7 N1 1.288(6) . ? N1 C8 1.388(6) . ? N1 B1 1.580(7) . ? C19 C18 1.363(8) . ? C19 C14 1.391(7) . ? C14 C15 1.406(8) . ? C14 B1 1.604(8) . ? C20 C21 1.509(9) . ? C15 C16 1.374(8) . ? C22 C23 1.487(8) . ? C5 C4 1.436(8) . ? C10 C9 1.371(7) . ? C10 C11 1.405(7) . ? C16 C17 1.365(7) . ? C11 C12 1.349(8) . ? C9 C8 1.392(7) . ? C8 C13 1.394(8) . ? C13 C12 1.379(8) . ? C18 C17 1.383(8) . ? C3 C2 1.365(7) . ? C3 C4 1.391(7) . ? 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 C9 O1 B1 106.9(4) . . ? C2 O2 B1 116.4(4) . . ? O3 N3 O4 123.1(5) . . ? O3 N3 C11 117.8(5) . . ? O4 N3 C11 119.1(5) . . ? C4 N2 C20 122.8(5) . . ? C4 N2 C22 120.2(5) . . ? C20 N2 C22 116.9(5) . . ? C6 C1 C7 123.9(5) . . ? C6 C1 C2 117.4(5) . . ? C7 C1 C2 118.1(5) . . ? C5 C6 C1 122.6(6) . . ? N1 C7 C1 120.3(5) . . ? C7 N1 C8 131.5(5) . . ? C7 N1 B1 120.8(4) . . ? C8 N1 B1 106.9(4) . . ? C18 C19 C14 123.0(6) . . ? C19 C14 C15 115.9(5) . . ? C19 C14 B1 121.6(5) . . ? C15 C14 B1 122.4(5) . . ? N2 C20 C21 113.7(5) . . ? C16 C15 C14 121.4(5) . . ? N2 C22 C23 114.6(5) . . ? C6 C5 C4 120.4(6) . . ? C9 C10 C11 115.7(5) . . ? C17 C16 C15 120.4(5) . . ? C12 C11 C10 124.0(5) . . ? C12 C11 N3 119.3(5) . . ? C10 C11 N3 116.7(5) . . ? O1 C9 C10 125.0(5) . . ? O1 C9 C8 114.3(5) . . ? C10 C9 C8 120.6(5) . . ? N1 C8 C9 107.3(5) . . ? N1 C8 C13 130.2(5) . . ? C9 C8 C13 122.4(5) . . ? C12 C13 C8 116.5(6) . . ? C19 C18 C17 119.3(6) . . ? C11 C12 C13 120.6(5) . . ? C2 C3 C4 122.9(5) . . ? N2 C4 C3 123.0(5) . . ? N2 C4 C5 119.8(5) . . ? C3 C4 C5 117.1(5) . . ? C16 C17 C18 119.9(5) . . ? C16 C17 Br1 119.8(4) . . ? C18 C17 Br1 120.2(4) . . ? O2 C2 C3 119.1(4) . . ? O2 C2 C1 121.4(4) . . ? C3 C2 C1 119.5(5) . . ? O2 B1 O1 111.6(4) . . ? O2 B1 N1 107.6(4) . . ? O1 B1 N1 100.6(4) . . ? O2 B1 C14 112.0(4) . . ? O1 B1 C14 112.3(4) . . ? N1 B1 C14 112.2(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 C1 C6 C5 -173.1(5) . . . . ? C2 C1 C6 C5 -1.9(8) . . . . ? C6 C1 C7 N1 -174.1(5) . . . . ? C2 C1 C7 N1 14.8(7) . . . . ? C1 C7 N1 C8 -161.3(5) . . . . ? C1 C7 N1 B1 6.8(7) . . . . ? C18 C19 C14 C15 -0.8(8) . . . . ? C18 C19 C14 B1 179.2(5) . . . . ? C4 N2 C20 C21 71.8(7) . . . . ? C22 N2 C20 C21 -103.5(6) . . . . ? C19 C14 C15 C16 0.4(7) . . . . ? B1 C14 C15 C16 -179.5(5) . . . . ? C4 N2 C22 C23 -86.4(7) . . . . ? C20 N2 C22 C23 89.1(7) . . . . ? C1 C6 C5 C4 1.0(8) . . . . ? C14 C15 C16 C17 1.1(8) . . . . ? C9 C10 C11 C12 1.1(7) . . . . ? C9 C10 C11 N3 -179.4(4) . . . . ? O3 N3 C11 C12 -7.7(8) . . . . ? O4 N3 C11 C12 171.0(5) . . . . ? O3 N3 C11 C10 172.7(5) . . . . ? O4 N3 C11 C10 -8.5(7) . . . . ? B1 O1 C9 C10 -169.6(5) . . . . ? B1 O1 C9 C8 13.0(5) . . . . ? C11 C10 C9 O1 -178.6(4) . . . . ? C11 C10 C9 C8 -1.4(7) . . . . ? C7 N1 C8 C9 157.1(5) . . . . ? B1 N1 C8 C9 -12.2(5) . . . . ? C7 N1 C8 C13 -20.2(8) . . . . ? B1 N1 C8 C13 170.5(5) . . . . ? O1 C9 C8 N1 0.0(5) . . . . ? C10 C9 C8 N1 -177.5(4) . . . . ? O1 C9 C8 C13 177.5(4) . . . . ? C10 C9 C8 C13 0.0(7) . . . . ? N1 C8 C13 C12 178.7(5) . . . . ? C9 C8 C13 C12 1.8(7) . . . . ? C14 C19 C18 C17 -0.5(9) . . . . ? C10 C11 C12 C13 0.8(8) . . . . ? N3 C11 C12 C13 -178.8(5) . . . . ? C8 C13 C12 C11 -2.2(8) . . . . ? C20 N2 C4 C3 -172.6(5) . . . . ? C22 N2 C4 C3 2.6(7) . . . . ? C20 N2 C4 C5 10.5(7) . . . . ? C22 N2 C4 C5 -174.3(5) . . . . ? C2 C3 C4 N2 180.0(5) . . . . ? C2 C3 C4 C5 -3.0(7) . . . . ? C6 C5 C4 N2 178.6(5) . . . . ? C6 C5 C4 C3 1.4(7) . . . . ? C15 C16 C17 C18 -2.4(8) . . . . ? C15 C16 C17 Br1 176.4(4) . . . . ? C19 C18 C17 C16 2.1(9) . . . . ? C19 C18 C17 Br1 -176.8(4) . . . . ? B1 O2 C2 C3 156.1(5) . . . . ? B1 O2 C2 C1 -27.0(6) . . . . ? C4 C3 C2 O2 179.0(4) . . . . ? C4 C3 C2 C1 2.1(7) . . . . ? C6 C1 C2 O2 -176.5(4) . . . . ? C7 C1 C2 O2 -4.7(7) . . . . ? C6 C1 C2 C3 0.4(7) . . . . ? C7 C1 C2 C3 172.1(5) . . . . ? C2 O2 B1 O1 153.0(4) . . . . ? C2 O2 B1 N1 43.6(5) . . . . ? C2 O2 B1 C14 -80.1(5) . . . . ? C9 O1 B1 O2 -132.4(4) . . . . ? C9 O1 B1 N1 -18.5(5) . . . . ? C9 O1 B1 C14 101.0(5) . . . . ? C7 N1 B1 O2 -35.1(6) . . . . ? C8 N1 B1 O2 135.7(4) . . . . ? C7 N1 B1 O1 -151.9(4) . . . . ? C8 N1 B1 O1 18.8(5) . . . . ? C7 N1 B1 C14 88.5(6) . . . . ? C8 N1 B1 C14 -100.8(5) . . . . ? C19 C14 B1 O2 -34.2(7) . . . . ? C15 C14 B1 O2 145.7(5) . . . . ? C19 C14 B1 O1 92.3(6) . . . . ? C15 C14 B1 O1 -87.8(6) . . . . ? C19 C14 B1 N1 -155.3(5) . . . . ? C15 C14 B1 N1 24.6(7) . . . . ?