# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 _publ_contact_author_name 'Duncan W. Bruce' _publ_contact_author_address ; Department of Chemistry University of York Heslington York YO10 5DD UNITED KINGDOM ; _publ_contact_author_email DB519@YORK.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Mesogenic, trimeric, halogen-bonded complexes from alkoxystilbazoles and 1,4-dihalotetrafluorobenzene ; loop_ _publ_author_name _publ_author_address 'Bruce, Duncan W' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Prasang, Carsten' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Whitwood, Adrian C.' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Chaux, Fanny' ;NFMLab-DCMIC ?G. Natta? 7 via Mancinelli I-20131 Milan Italy ; 'Metrangolo, Pierangelo' ;NFMLab-DCMIC ?G. Natta? 7 via Mancinelli I-20131 Milan Italy ; 'Meyer, Franck' ;NFMLab-DCMIC ?G. Natta? 7 via Mancinelli I-20131 Milan Italy ; 'Resnati, Giuseppe' ;NFMLab-DCMIC ?G. Natta? 7 via Mancinelli I-20131 Milan Italy ; data_Iodo_LC_3-8 _database_code_depnum_ccdc_archive 'CCDC 665553' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O, 0.5(C6 F4 I2)' _chemical_formula_sum 'C24 H27 F2 I N O' _chemical_formula_weight 510.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6014(8) _cell_length_b 12.5366(13) _cell_length_c 13.2340(14) _cell_angle_alpha 114.368(2) _cell_angle_beta 91.703(2) _cell_angle_gamma 106.360(2) _cell_volume 1086.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6050 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 28.29 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 1.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.728 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11209 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5337 _reflns_number_gt 4888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+0.1918P] 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 5337 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0570 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6013(3) 0.12773(17) 0.04439(15) 0.0188(4) Uani 1 1 d . . . C2 C 0.6893(3) 0.03844(18) 0.01472(16) 0.0193(4) Uani 1 1 d . . . C3 C 0.5908(3) -0.08516(18) -0.02806(16) 0.0196(4) Uani 1 1 d . . . F1 F 0.87656(16) 0.07334(11) 0.02821(11) 0.0277(3) Uani 1 1 d . . . F2 F 0.68663(16) -0.16589(11) -0.05283(10) 0.0266(3) Uani 1 1 d . . . I1 I 0.752119(17) 0.316364(11) 0.108098(10) 0.01967(5) Uani 1 1 d . . . C4 C 0.0291(3) -0.34398(18) 0.27985(16) 0.0211(4) Uani 1 1 d . . . H4 H 0.0592 -0.3702 0.3341 0.025 Uiso 1 1 calc R . . C5 C 0.0796(3) -0.21849(18) 0.31074(16) 0.0204(4) Uani 1 1 d . . . H5 H 0.1429 -0.1608 0.3846 0.025 Uiso 1 1 calc R . . C6 C 0.0376(3) -0.17661(18) 0.23340(16) 0.0187(4) Uani 1 1 d . . . C7 C -0.0527(3) -0.26742(18) 0.12584(16) 0.0213(4) Uani 1 1 d . . . H7 H -0.0823 -0.2444 0.0692 0.026 Uiso 1 1 calc R . . C8 C -0.0986(3) -0.39080(18) 0.10270(17) 0.0230(4) Uani 1 1 d . . . H8 H -0.1610 -0.4508 0.0293 0.028 Uiso 1 1 calc R . . C9 C 0.0786(3) -0.04641(18) 0.25798(17) 0.0206(4) Uani 1 1 d . . . H9 H 0.0531 -0.0292 0.1966 0.025 Uiso 1 1 calc R . . C10 C 0.1485(3) 0.05092(18) 0.35836(16) 0.0197(4) Uani 1 1 d . . . H10 H 0.1805 0.0342 0.4190 0.024 Uiso 1 1 calc R . . C11 C 0.1801(3) 0.18053(17) 0.38346(16) 0.0182(4) Uani 1 1 d . . . C12 C 0.1471(3) 0.21848(18) 0.30051(16) 0.0208(4) Uani 1 1 d . . . H12 H 0.1083 0.1588 0.2241 0.025 Uiso 1 1 calc R . . C13 C 0.1699(3) 0.34045(18) 0.32823(16) 0.0200(4) Uani 1 1 d . . . H13 H 0.1480 0.3644 0.2709 0.024 Uiso 1 1 calc R . . C14 C 0.2251(3) 0.42947(17) 0.43997(16) 0.0182(4) Uani 1 1 d . . . C15 C 0.2641(3) 0.39534(18) 0.52364(16) 0.0197(4) Uani 1 1 d . . . H15 H 0.3062 0.4557 0.5996 0.024 Uiso 1 1 calc R . . C16 C 0.2403(3) 0.27176(18) 0.49420(16) 0.0192(4) Uani 1 1 d . . . H16 H 0.2660 0.2484 0.5514 0.023 Uiso 1 1 calc R . . C17 C 0.2923(3) 0.64267(17) 0.57084(15) 0.0192(4) Uani 1 1 d . . . H17A H 0.4181 0.6513 0.6024 0.023 Uiso 1 1 calc R . . H17B H 0.2040 0.6241 0.6195 0.023 Uiso 1 1 calc R . . C18 C 0.2919(3) 0.75970(18) 0.56359(16) 0.0204(4) Uani 1 1 d . . . H18A H 0.1640 0.7492 0.5339 0.025 Uiso 1 1 calc R . . H18B H 0.3724 0.7716 0.5091 0.025 Uiso 1 1 calc R . . C19 C 0.3586(3) 0.87568(17) 0.67494(16) 0.0192(4) Uani 1 1 d . . . H19A H 0.4811 0.8826 0.7095 0.023 Uiso 1 1 calc R . . H19B H 0.2697 0.8696 0.7271 0.023 Uiso 1 1 calc R . . C20 C 0.3751(3) 0.99071(17) 0.65728(16) 0.0197(4) Uani 1 1 d . . . H20A H 0.4616 0.9942 0.6034 0.024 Uiso 1 1 calc R . . H20B H 0.2518 0.9822 0.6225 0.024 Uiso 1 1 calc R . . C21 C 0.4431(3) 1.11218(17) 0.76343(16) 0.0194(4) Uani 1 1 d . . . H21A H 0.5667 1.1218 0.7988 0.023 Uiso 1 1 calc R . . H21B H 0.3562 1.1103 0.8174 0.023 Uiso 1 1 calc R . . C22 C 0.4574(3) 1.22259(18) 0.73915(15) 0.0193(4) Uani 1 1 d . . . H22A H 0.5262 1.2155 0.6755 0.023 Uiso 1 1 calc R . . H22B H 0.3305 1.2190 0.7151 0.023 Uiso 1 1 calc R . . C23 C 0.5535(3) 1.34789(18) 0.83805(16) 0.0210(4) Uani 1 1 d . . . H23A H 0.4837 1.3567 0.9014 0.025 Uiso 1 1 calc R . . H23B H 0.6803 1.3520 0.8631 0.025 Uiso 1 1 calc R . . C24 C 0.5665(3) 1.45420(19) 0.80791(19) 0.0278(4) Uani 1 1 d . . . H24A H 0.6337 1.4451 0.7444 0.042 Uiso 1 1 calc R . . H24B H 0.6331 1.5328 0.8728 0.042 Uiso 1 1 calc R . . H24C H 0.4410 1.4532 0.7871 0.042 Uiso 1 1 calc R . . N1 N -0.0604(2) -0.43070(15) 0.17715(14) 0.0226(3) Uani 1 1 d . . . O1 O 0.2367(2) 0.54623(12) 0.45774(11) 0.0211(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0241(10) 0.0164(9) 0.0161(9) 0.0076(7) 0.0026(7) 0.0062(7) C2 0.0161(9) 0.0224(10) 0.0202(9) 0.0104(8) 0.0023(7) 0.0062(7) C3 0.0243(10) 0.0197(9) 0.0188(9) 0.0088(7) 0.0039(7) 0.0122(8) F1 0.0176(6) 0.0257(6) 0.0379(7) 0.0120(6) 0.0031(5) 0.0072(5) F2 0.0247(6) 0.0213(6) 0.0355(7) 0.0105(5) 0.0061(5) 0.0128(5) I1 0.02299(7) 0.01711(7) 0.01759(7) 0.00688(5) 0.00181(5) 0.00584(5) C4 0.0220(10) 0.0189(9) 0.0209(9) 0.0077(8) 0.0033(8) 0.0061(8) C5 0.0204(9) 0.0184(9) 0.0185(9) 0.0055(7) 0.0019(7) 0.0047(7) C6 0.0152(9) 0.0187(9) 0.0215(9) 0.0079(8) 0.0057(7) 0.0056(7) C7 0.0217(10) 0.0223(10) 0.0190(9) 0.0084(8) 0.0031(7) 0.0070(8) C8 0.0224(10) 0.0201(10) 0.0195(9) 0.0038(8) -0.0001(8) 0.0045(8) C9 0.0198(9) 0.0193(9) 0.0235(9) 0.0105(8) 0.0039(7) 0.0058(7) C10 0.0181(9) 0.0197(9) 0.0230(9) 0.0107(8) 0.0038(7) 0.0066(7) C11 0.0164(8) 0.0173(9) 0.0195(9) 0.0071(7) 0.0029(7) 0.0048(7) C12 0.0222(10) 0.0191(9) 0.0168(9) 0.0051(7) 0.0007(7) 0.0047(8) C13 0.0228(10) 0.0201(9) 0.0175(9) 0.0094(8) 0.0010(7) 0.0060(8) C14 0.0171(9) 0.0167(9) 0.0207(9) 0.0084(7) 0.0024(7) 0.0048(7) C15 0.0204(9) 0.0191(9) 0.0163(9) 0.0058(7) 0.0009(7) 0.0048(7) C16 0.0204(9) 0.0206(9) 0.0177(9) 0.0099(8) 0.0019(7) 0.0061(7) C17 0.0215(9) 0.0181(9) 0.0164(9) 0.0057(7) 0.0023(7) 0.0072(7) C18 0.0232(10) 0.0191(9) 0.0183(9) 0.0077(8) 0.0019(7) 0.0068(8) C19 0.0205(9) 0.0187(9) 0.0179(9) 0.0078(7) 0.0027(7) 0.0062(7) C20 0.0210(9) 0.0183(9) 0.0176(9) 0.0068(7) 0.0014(7) 0.0048(7) C21 0.0204(9) 0.0188(9) 0.0178(9) 0.0074(7) 0.0017(7) 0.0056(7) C22 0.0202(9) 0.0215(9) 0.0175(9) 0.0097(8) 0.0026(7) 0.0070(8) C23 0.0224(9) 0.0193(9) 0.0194(9) 0.0064(8) 0.0011(7) 0.0073(8) C24 0.0330(12) 0.0197(10) 0.0298(11) 0.0105(9) 0.0021(9) 0.0082(9) N1 0.0217(8) 0.0170(8) 0.0248(9) 0.0065(7) 0.0040(7) 0.0042(7) O1 0.0299(8) 0.0149(6) 0.0164(6) 0.0051(5) 0.0002(5) 0.0074(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.382(3) 2_655 ? C1 C2 1.389(3) . ? C1 I1 2.0946(19) . ? C2 F1 1.349(2) . ? C2 C3 1.371(3) . ? C3 F2 1.349(2) . ? C3 C1 1.382(3) 2_655 ? C4 N1 1.342(2) . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.394(3) . ? C5 H5 0.9500 . ? C6 C7 1.399(3) . ? C6 C9 1.462(3) . ? C7 C8 1.381(3) . ? C7 H7 0.9500 . ? C8 N1 1.333(3) . ? C8 H8 0.9500 . ? C9 C10 1.338(3) . ? C9 H9 0.9500 . ? C10 C11 1.462(3) . ? C10 H10 0.9500 . ? C11 C16 1.396(3) . ? C11 C12 1.406(3) . ? C12 C13 1.373(3) . ? C12 H12 0.9500 . ? C13 C14 1.395(3) . ? C13 H13 0.9500 . ? C14 O1 1.359(2) . ? C14 C15 1.393(3) . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O1 1.436(2) . ? C17 C18 1.510(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.521(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.526(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.519(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.522(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.521(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.521(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 C2 116.39(17) 2_655 . ? C3 C1 I1 121.98(14) 2_655 . ? C2 C1 I1 121.62(14) . . ? F1 C2 C3 118.69(17) . . ? F1 C2 C1 119.60(17) . . ? C3 C2 C1 121.71(17) . . ? F2 C3 C2 118.11(17) . . ? F2 C3 C1 119.98(17) . 2_655 ? C2 C3 C1 121.90(17) . 2_655 ? N1 C4 C5 123.33(18) . . ? N1 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C4 C5 C6 119.93(18) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 116.51(18) . . ? C5 C6 C9 124.59(18) . . ? C7 C6 C9 118.90(18) . . ? C8 C7 C6 119.52(18) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? N1 C8 C7 123.90(18) . . ? N1 C8 H8 118.0 . . ? C7 C8 H8 118.0 . . ? C10 C9 C6 126.45(19) . . ? C10 C9 H9 116.8 . . ? C6 C9 H9 116.8 . . ? C9 C10 C11 126.11(18) . . ? C9 C10 H10 116.9 . . ? C11 C10 H10 116.9 . . ? C16 C11 C12 117.44(17) . . ? C16 C11 C10 119.79(17) . . ? C12 C11 C10 122.74(17) . . ? C13 C12 C11 121.02(17) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.50(18) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? O1 C14 C15 124.91(17) . . ? O1 C14 C13 115.27(16) . . ? C15 C14 C13 119.82(17) . . ? C16 C15 C14 118.90(17) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C11 122.27(18) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? O1 C17 C18 106.02(15) . . ? O1 C17 H17A 110.5 . . ? C18 C17 H17A 110.5 . . ? O1 C17 H17B 110.5 . . ? C18 C17 H17B 110.5 . . ? H17A C17 H17B 108.7 . . ? C17 C18 C19 114.41(16) . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C18 C19 C20 110.70(15) . . ? C18 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C19 114.97(16) . . ? C21 C20 H20A 108.5 . . ? C19 C20 H20A 108.5 . . ? C21 C20 H20B 108.5 . . ? C19 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C20 C21 C22 111.97(15) . . ? C20 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? C20 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C21 114.61(16) . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C22 112.07(17) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C8 N1 C4 116.80(17) . . ? C14 O1 C17 118.33(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 F1 179.89(17) 2_655 . . . ? I1 C1 C2 F1 0.8(2) . . . . ? C3 C1 C2 C3 -0.2(3) 2_655 . . . ? I1 C1 C2 C3 -179.33(14) . . . . ? F1 C2 C3 F2 1.1(3) . . . . ? C1 C2 C3 F2 -178.78(17) . . . . ? F1 C2 C3 C1 -179.88(17) . . . 2_655 ? C1 C2 C3 C1 0.2(3) . . . 2_655 ? N1 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C7 -1.1(3) . . . . ? C4 C5 C6 C9 177.80(18) . . . . ? C5 C6 C7 C8 1.4(3) . . . . ? C9 C6 C7 C8 -177.57(18) . . . . ? C6 C7 C8 N1 -0.7(3) . . . . ? C5 C6 C9 C10 -5.3(3) . . . . ? C7 C6 C9 C10 173.62(19) . . . . ? C6 C9 C10 C11 -176.61(18) . . . . ? C9 C10 C11 C16 174.94(19) . . . . ? C9 C10 C11 C12 -3.1(3) . . . . ? C16 C11 C12 C13 -1.2(3) . . . . ? C10 C11 C12 C13 176.84(18) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 O1 -177.72(18) . . . . ? C12 C13 C14 C15 2.4(3) . . . . ? O1 C14 C15 C16 177.79(18) . . . . ? C13 C14 C15 C16 -2.4(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C10 C11 C16 C15 -176.86(18) . . . . ? O1 C17 C18 C19 -176.61(15) . . . . ? C17 C18 C19 C20 173.36(17) . . . . ? C18 C19 C20 C21 -179.31(16) . . . . ? C19 C20 C21 C22 179.58(16) . . . . ? C20 C21 C22 C23 -170.67(16) . . . . ? C21 C22 C23 C24 179.00(17) . . . . ? C7 C8 N1 C4 -0.5(3) . . . . ? C5 C4 N1 C8 0.8(3) . . . . ? C15 C14 O1 C17 -0.3(3) . . . . ? C13 C14 O1 C17 179.87(16) . . . . ? C18 C17 O1 C14 -179.94(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.982 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.080 #===END data_Bromo_LC_3-8 _database_code_depnum_ccdc_archive 'CCDC 665554' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O, 0.5(C6 Br2 F4)' _chemical_formula_sum 'C24 H27 Br F2 N O' _chemical_formula_weight 463.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6549(7) _cell_length_b 12.1014(12) _cell_length_c 13.0598(13) _cell_angle_alpha 109.606(2) _cell_angle_beta 92.273(2) _cell_angle_gamma 107.571(2) _cell_volume 1073.01(18) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5915 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 29.98 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 478 _exptl_absorpt_coefficient_mu 1.947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12387 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 29.99 _reflns_number_total 6092 _reflns_number_gt 5522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.1689P] 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 6092 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0358(2) 0.13989(14) 0.27397(13) 0.0232(3) Uani 1 1 d . . . H1 H 0.0653 0.1089 0.3279 0.028 Uiso 1 1 calc R . . C2 C 0.0783(2) 0.26743(14) 0.30439(13) 0.0219(3) Uani 1 1 d . . . H2 H 0.1356 0.3215 0.3773 0.026 Uiso 1 1 calc R . . C3 C 0.03619(19) 0.31620(13) 0.22701(12) 0.0190(3) Uani 1 1 d . . . C4 C -0.0456(2) 0.23045(14) 0.12129(12) 0.0224(3) Uani 1 1 d . . . H4 H -0.0754 0.2583 0.0651 0.027 Uiso 1 1 calc R . . C5 C -0.0831(2) 0.10444(14) 0.09890(13) 0.0249(3) Uani 1 1 d . . . H5 H -0.1396 0.0479 0.0266 0.030 Uiso 1 1 calc R . . C6 C 0.0714(2) 0.44899(14) 0.25191(13) 0.0211(3) Uani 1 1 d . . . H6 H 0.0465 0.4733 0.1924 0.025 Uiso 1 1 calc R . . C7 C 0.1356(2) 0.53920(13) 0.35118(12) 0.0211(3) Uani 1 1 d . . . H7 H 0.1643 0.5146 0.4098 0.025 Uiso 1 1 calc R . . C8 C 0.1661(2) 0.67203(13) 0.37868(12) 0.0197(3) Uani 1 1 d . . . C9 C 0.1308(2) 0.72176(14) 0.30038(12) 0.0207(3) Uani 1 1 d . . . H9 H 0.0888 0.6684 0.2255 0.025 Uiso 1 1 calc R . . C10 C 0.1559(2) 0.84657(14) 0.33037(12) 0.0211(3) Uani 1 1 d . . . H10 H 0.1307 0.8785 0.2763 0.025 Uiso 1 1 calc R . . C11 C 0.2184(2) 0.92690(13) 0.44047(12) 0.0193(3) Uani 1 1 d . . . C12 C 0.2571(2) 0.88061(14) 0.51945(12) 0.0215(3) Uani 1 1 d . . . H12 H 0.3015 0.9345 0.5940 0.026 Uiso 1 1 calc R . . C13 C 0.2297(2) 0.75377(14) 0.48758(12) 0.0214(3) Uani 1 1 d . . . H13 H 0.2550 0.7219 0.5417 0.026 Uiso 1 1 calc R . . C14 C 0.2958(2) 1.13652(13) 0.57094(12) 0.0212(3) Uani 1 1 d . . . H14A H 0.4211 1.1418 0.5993 0.025 Uiso 1 1 calc R . . H14B H 0.2088 1.1127 0.6201 0.025 Uiso 1 1 calc R . . C15 C 0.2986(2) 1.25947(13) 0.56427(12) 0.0215(3) Uani 1 1 d . . . H15A H 0.1717 1.2512 0.5357 0.026 Uiso 1 1 calc R . . H15B H 0.3800 1.2778 0.5108 0.026 Uiso 1 1 calc R . . C16 C 0.3655(2) 1.36908(13) 0.67348(12) 0.0209(3) Uani 1 1 d . . . H16A H 0.4882 1.3742 0.7059 0.025 Uiso 1 1 calc R . . H16B H 0.2776 1.3558 0.7253 0.025 Uiso 1 1 calc R . . C17 C 0.3811(2) 1.49095(14) 0.65796(12) 0.0214(3) Uani 1 1 d . . . H17A H 0.4709 1.5039 0.6071 0.026 Uiso 1 1 calc R . . H17B H 0.2590 1.4834 0.6227 0.026 Uiso 1 1 calc R . . C18 C 0.4421(2) 1.60500(13) 0.76403(12) 0.0205(3) Uani 1 1 d . . . H18A H 0.5649 1.6136 0.7992 0.025 Uiso 1 1 calc R . . H18B H 0.3527 1.5925 0.8153 0.025 Uiso 1 1 calc R . . C19 C 0.4546(2) 1.72472(13) 0.74525(12) 0.0198(3) Uani 1 1 d . . . H19A H 0.5297 1.7305 0.6860 0.024 Uiso 1 1 calc R . . H19B H 0.3284 1.7201 0.7194 0.024 Uiso 1 1 calc R . . C20 C 0.5395(2) 1.84244(14) 0.84658(13) 0.0229(3) Uani 1 1 d . . . H20A H 0.6666 1.8484 0.8724 0.027 Uiso 1 1 calc R . . H20B H 0.4650 1.8375 0.9061 0.027 Uiso 1 1 calc R . . C21 C 0.5479(3) 1.95901(15) 0.82319(15) 0.0315(4) Uani 1 1 d . . . H21A H 0.6155 1.9617 0.7614 0.047 Uiso 1 1 calc R . . H21B H 0.6119 2.0330 0.8886 0.047 Uiso 1 1 calc R . . H21C H 0.4216 1.9573 0.8045 0.047 Uiso 1 1 calc R . . N1 N -0.04444(18) 0.05781(12) 0.17291(12) 0.0252(3) Uani 1 1 d . . . O1 O 0.23540(16) 1.04773(10) 0.46015(9) 0.0236(2) Uani 1 1 d . . . Br1 Br -0.25085(2) -0.202619(12) 0.104483(11) 0.02206(5) Uani 1 1 d . . . C22 C -0.3939(2) -0.37228(13) 0.04584(11) 0.0194(3) Uani 1 1 d . . . C23 C -0.5859(2) -0.41214(14) 0.03185(12) 0.0207(3) Uani 1 1 d . . . C24 C -0.3104(2) -0.46327(14) 0.01304(12) 0.0205(3) Uani 1 1 d . . . F1 F -0.67430(13) -0.32856(9) 0.06065(8) 0.0285(2) Uani 1 1 d . . . F2 F -0.12446(12) -0.43017(9) 0.02568(8) 0.0279(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0231(7) 0.0219(7) 0.0259(7) 0.0103(6) 0.0046(6) 0.0075(6) C2 0.0221(7) 0.0210(7) 0.0209(7) 0.0061(6) 0.0020(5) 0.0068(5) C3 0.0156(6) 0.0195(6) 0.0218(7) 0.0072(5) 0.0045(5) 0.0058(5) C4 0.0221(7) 0.0230(7) 0.0214(7) 0.0080(6) 0.0033(5) 0.0068(6) C5 0.0244(7) 0.0216(7) 0.0238(7) 0.0044(6) 0.0007(6) 0.0054(6) C6 0.0214(7) 0.0205(7) 0.0236(7) 0.0102(6) 0.0043(5) 0.0076(5) C7 0.0213(7) 0.0202(7) 0.0244(7) 0.0098(6) 0.0037(5) 0.0085(5) C8 0.0184(6) 0.0200(6) 0.0207(7) 0.0073(5) 0.0031(5) 0.0068(5) C9 0.0223(7) 0.0205(7) 0.0173(6) 0.0058(5) 0.0019(5) 0.0058(5) C10 0.0236(7) 0.0217(7) 0.0182(6) 0.0084(5) 0.0007(5) 0.0069(5) C11 0.0198(6) 0.0180(6) 0.0201(7) 0.0068(5) 0.0031(5) 0.0065(5) C12 0.0232(7) 0.0230(7) 0.0176(6) 0.0061(5) 0.0011(5) 0.0087(6) C13 0.0239(7) 0.0230(7) 0.0190(7) 0.0094(6) 0.0015(5) 0.0087(6) C14 0.0233(7) 0.0193(6) 0.0181(6) 0.0042(5) 0.0012(5) 0.0063(5) C15 0.0228(7) 0.0204(7) 0.0190(6) 0.0058(5) 0.0012(5) 0.0060(5) C16 0.0209(7) 0.0206(7) 0.0194(7) 0.0061(5) 0.0025(5) 0.0061(5) C17 0.0245(7) 0.0207(7) 0.0172(6) 0.0058(5) 0.0019(5) 0.0063(5) C18 0.0218(7) 0.0203(7) 0.0170(6) 0.0054(5) 0.0015(5) 0.0054(5) C19 0.0189(6) 0.0208(7) 0.0180(6) 0.0064(5) 0.0020(5) 0.0053(5) C20 0.0233(7) 0.0209(7) 0.0218(7) 0.0048(6) -0.0002(5) 0.0074(6) C21 0.0344(9) 0.0219(7) 0.0368(9) 0.0092(7) 0.0022(7) 0.0097(7) N1 0.0238(6) 0.0194(6) 0.0301(7) 0.0076(5) 0.0037(5) 0.0056(5) O1 0.0338(6) 0.0178(5) 0.0178(5) 0.0047(4) -0.0007(4) 0.0092(4) Br1 0.02539(8) 0.01798(8) 0.02046(8) 0.00637(6) 0.00099(5) 0.00507(6) C22 0.0235(7) 0.0182(6) 0.0157(6) 0.0061(5) 0.0019(5) 0.0061(5) C23 0.0257(7) 0.0205(7) 0.0185(6) 0.0073(5) 0.0036(5) 0.0112(6) C24 0.0187(6) 0.0233(7) 0.0197(6) 0.0085(5) 0.0020(5) 0.0066(5) F1 0.0278(5) 0.0233(4) 0.0365(5) 0.0079(4) 0.0069(4) 0.0145(4) F2 0.0185(4) 0.0270(5) 0.0365(5) 0.0099(4) 0.0025(4) 0.0074(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.339(2) . ? C1 C2 1.386(2) . ? C1 H1 0.9500 . ? C2 C3 1.401(2) . ? C2 H2 0.9500 . ? C3 C4 1.397(2) . ? C3 C6 1.4634(19) . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 N1 1.336(2) . ? C5 H5 0.9500 . ? C6 C7 1.338(2) . ? C6 H6 0.9500 . ? C7 C8 1.465(2) . ? C7 H7 0.9500 . ? C8 C13 1.396(2) . ? C8 C9 1.404(2) . ? C9 C10 1.376(2) . ? C9 H9 0.9500 . ? C10 C11 1.403(2) . ? C10 H10 0.9500 . ? C11 O1 1.3607(17) . ? C11 C12 1.389(2) . ? C12 C13 1.394(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.4372(17) . ? C14 C15 1.513(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.525(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.525(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.520(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.524(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 Br1 2.8668(13) . ? Br1 C22 1.8766(14) . ? C22 C23 1.385(2) . ? C22 C24 1.391(2) . ? C23 F1 1.3418(16) . ? C23 C24 1.376(2) 2_445 ? C24 F2 1.3441(16) . ? C24 C23 1.376(2) 2_445 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.73(14) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 119.62(14) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 116.52(13) . . ? C4 C3 C6 119.80(13) . . ? C2 C3 C6 123.68(13) . . ? C5 C4 C3 119.56(14) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 123.93(14) . . ? N1 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? C7 C6 C3 125.70(14) . . ? C7 C6 H6 117.1 . . ? C3 C6 H6 117.1 . . ? C6 C7 C8 126.65(14) . . ? C6 C7 H7 116.7 . . ? C8 C7 H7 116.7 . . ? C13 C8 C9 117.71(13) . . ? C13 C8 C7 119.34(13) . . ? C9 C8 C7 122.93(13) . . ? C10 C9 C8 121.04(13) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.30(13) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? O1 C11 C12 125.24(13) . . ? O1 C11 C10 114.84(12) . . ? C12 C11 C10 119.92(13) . . ? C11 C12 C13 118.93(13) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C8 122.09(13) . . ? C12 C13 H13 119.0 . . ? C8 C13 H13 119.0 . . ? O1 C14 C15 105.39(12) . . ? O1 C14 H14A 110.7 . . ? C15 C14 H14A 110.7 . . ? O1 C14 H14B 110.7 . . ? C15 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C14 C15 C16 114.32(12) . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 111.05(12) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 114.38(12) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 112.81(12) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 114.24(12) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 111.97(13) . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20B 109.2 . . ? C21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C5 N1 C1 116.62(13) . . ? C5 N1 Br1 111.18(10) . . ? C1 N1 Br1 129.16(10) . . ? C11 O1 C14 118.80(11) . . ? C22 Br1 N1 174.11(5) . . ? C23 C22 C24 117.27(13) . . ? C23 C22 Br1 121.72(11) . . ? C24 C22 Br1 121.00(11) . . ? F1 C23 C24 118.77(13) . 2_445 ? F1 C23 C22 119.97(13) . . ? C24 C23 C22 121.25(13) 2_445 . ? F2 C24 C23 118.61(13) . 2_445 ? F2 C24 C22 119.91(13) . . ? C23 C24 C22 121.47(13) 2_445 . ? 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 N1 C1 C2 C3 0.2(2) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C1 C2 C3 C6 178.45(13) . . . . ? C2 C3 C4 C5 1.0(2) . . . . ? C6 C3 C4 C5 -178.32(14) . . . . ? C3 C4 C5 N1 -0.5(2) . . . . ? C4 C3 C6 C7 174.67(14) . . . . ? C2 C3 C6 C7 -4.6(2) . . . . ? C3 C6 C7 C8 -177.87(14) . . . . ? C6 C7 C8 C13 178.35(15) . . . . ? C6 C7 C8 C9 -0.4(2) . . . . ? C13 C8 C9 C10 -0.8(2) . . . . ? C7 C8 C9 C10 177.95(14) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C9 C10 C11 O1 -179.12(13) . . . . ? C9 C10 C11 C12 0.7(2) . . . . ? O1 C11 C12 C13 178.70(14) . . . . ? C10 C11 C12 C13 -1.1(2) . . . . ? C11 C12 C13 C8 0.6(2) . . . . ? C9 C8 C13 C12 0.4(2) . . . . ? C7 C8 C13 C12 -178.42(14) . . . . ? O1 C14 C15 C16 -178.11(12) . . . . ? C14 C15 C16 C17 174.81(13) . . . . ? C15 C16 C17 C18 178.34(12) . . . . ? C16 C17 C18 C19 -179.60(12) . . . . ? C17 C18 C19 C20 -172.23(12) . . . . ? C18 C19 C20 C21 -179.75(13) . . . . ? C4 C5 N1 C1 -0.2(2) . . . . ? C4 C5 N1 Br1 161.88(13) . . . . ? C2 C1 N1 C5 0.4(2) . . . . ? C2 C1 N1 Br1 -157.93(11) . . . . ? C12 C11 O1 C14 -0.8(2) . . . . ? C10 C11 O1 C14 179.02(13) . . . . ? C15 C14 O1 C11 -179.66(12) . . . . ? C24 C22 C23 F1 -179.14(13) . . . . ? Br1 C22 C23 F1 -0.08(19) . . . . ? C24 C22 C23 C24 -0.2(2) . . . 2_445 ? Br1 C22 C23 C24 178.84(11) . . . 2_445 ? C23 C22 C24 F2 -179.32(13) . . . . ? Br1 C22 C24 F2 1.62(19) . . . . ? C23 C22 C24 C23 0.2(2) . . . 2_445 ? Br1 C22 C24 C23 -178.85(11) . . . 2_445 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.595 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.076 #===END