# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' _audit_creation_method SHELXL-97 _publ_requested_journal 'test' _publ_contact_author_name 'Dr Graham Sanford' _publ_contact_author_address ; Department of Chemistry Univerisity of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'GRAHAM.SANFORD@DURHAM.AC.UK' _publ_contact_letter ; The CIF file contains data for the structure 15 from the paper "Polyhalogenated Heterocyclic Compounds. 47. Syntheses of multisubstituted pyridine derivatives from pentafluoropyridine" by R.D.Chambers, P.R.Hoskin, G.Sandford, D.S.Yufit and J.A.K.Howard The paper will be published in J.Chem.Soc.Perkin Trans ; loop_ _publ_author_name _publ_author_address 'Chambers, Richard D.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Hoskin, Philip R.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Sandford, Graham' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Yufit, Dmitrii S.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; 'Howard, Judith A.K.' ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; _publ_section_title ; Polyhalogenated Heterocyclic Compounds. Part 47. 1 Syntheses of multi-substituted pyridine derivatives from pentafluoropyridine ; data_187s _database_code_CSD 167082 _chemical_name_systematic ; 4-[1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl]- 2-bromo-3-fluoro-5-methoxy-6-piperidylpyridine ; _chemical_name_common ? _chemical_melting_point '81.1-83.0' _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 Br F8 N2 O' _chemical_formula_weight 457.17 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' '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 monoclinic _symmetry_space_group_name_H-M 'P 2~1~/c' 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 10.530(2) _cell_length_b 13.802(3) _cell_length_c 11.485(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.86(3) _cell_angle_gamma 90.00 _cell_volume 1669.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 997 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 20.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 2.553 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.3503 _exptl_absorpt_correction_T_max 0.5794 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(1) _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 SMART _diffrn_measurement_method '\w-scan' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17323 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3834 _reflns_number_gt 3118 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0700P)^2^+8.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.005(1) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3834 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1802 _refine_ls_wR_factor_gt 0.1712 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _refine_ls_shift/su_max 0.002 _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 Br1 Br 2.16671(5) 0.50691(4) 0.32714(4) 0.0394(2) Uani 1 1 d . . . F1 F 1.9361(3) 0.3966(2) 0.3933(2) 0.0411(7) Uani 1 1 d . . . O1 O 1.6669(3) 0.4920(3) 0.0762(3) 0.0392(9) Uani 1 1 d . . . N1 N 1.9888(4) 0.5627(3) 0.1598(3) 0.0240(7) Uani 1 1 d . . . N2 N 1.8556(3) 0.6335(3) 0.0172(3) 0.0237(7) Uani 1 1 d . . . C1 C 2.0060(5) 0.5043(3) 0.2503(4) 0.0272(9) Uani 1 1 d . . . C2 C 1.9121(5) 0.4460(3) 0.2942(4) 0.0308(10) Uani 1 1 d . . . C3 C 1.7966(5) 0.4391(4) 0.2344(4) 0.0341(10) Uani 1 1 d . . . C4 C 1.7789(5) 0.4987(3) 0.1358(4) 0.0300(10) Uani 1 1 d . . . C5 C 1.8751(4) 0.5648(3) 0.1057(4) 0.0244(8) Uani 1 1 d . . . C6 C 1.7490(5) 0.7008(4) 0.0391(4) 0.0329(10) Uani 1 1 d . . . H6A H 1.7722 0.7450 0.1039 0.039 Uiso 1 1 calc R . . H6B H 1.6732 0.6635 0.0622 0.039 Uiso 1 1 calc R . . C7 C 1.7183(5) 0.7598(4) -0.0701(4) 0.0360(11) Uani 1 1 d . . . H7A H 1.6491 0.8061 -0.0535 0.043 Uiso 1 1 calc R . . H7B H 1.6886 0.7159 -0.1330 0.043 Uiso 1 1 calc R . . C8 C 1.8358(5) 0.8156(3) -0.1107(4) 0.0325(10) Uani 1 1 d . . . H8A H 1.8158 0.8504 -0.1840 0.039 Uiso 1 1 calc R . . H8B H 1.8613 0.8639 -0.0511 0.039 Uiso 1 1 calc R . . C9 C 1.9436(5) 0.7444(3) -0.1299(4) 0.0321(10) Uani 1 1 d . . . H9A H 2.0210 0.7804 -0.1516 0.038 Uiso 1 1 calc R . . H9B H 1.9208 0.7005 -0.1950 0.038 Uiso 1 1 calc R . . C10 C 1.9710(4) 0.6846(3) -0.0201(4) 0.0266(9) Uani 1 1 d . . . H10A H 2.0387 0.6369 -0.0361 0.032 Uiso 1 1 calc R . . H10B H 2.0014 0.7279 0.0431 0.032 Uiso 1 1 calc R . . C14 C 1.6750(5) 0.4708(4) -0.0472(5) 0.0403(12) Uani 1 1 d . . . H14A H 1.5893 0.4671 -0.0813 0.060 Uiso 1 1 calc R . . H14B H 1.7184 0.4086 -0.0579 0.060 Uiso 1 1 calc R . . H14C H 1.7228 0.5222 -0.0858 0.060 Uiso 1 1 calc R . . F2 F 1.7543(5) 0.2978(4) 0.3471(4) 0.0451(11) Uiso 0.70 1 d P . . F3 F 1.7194(4) 0.2816(3) 0.0930(4) 0.0450(11) Uiso 0.70 1 d P . . F4 F 1.5346(4) 0.3399(4) 0.1292(4) 0.0436(10) Uiso 0.70 1 d P . . F5 F 1.6021(5) 0.2151(4) 0.2224(5) 0.0546(12) Uiso 0.70 1 d P . . F6 F 1.5447(8) 0.5170(6) 0.2945(7) 0.076(2) Uiso 0.70 1 d P . . F7 F 1.6514(6) 0.4510(5) 0.4422(5) 0.0573(17) Uiso 0.70 1 d P . . F8 F 1.4987(8) 0.3684(7) 0.3805(7) 0.078(2) Uiso 0.70 1 d P . . C11 C 1.6994(8) 0.3650(6) 0.2733(7) 0.0417(18) Uiso 0.80 1 d P . . C12 C 1.6411(7) 0.2973(5) 0.1716(6) 0.0408(15) Uiso 0.80 1 d P . . C13 C 1.6001(9) 0.4158(8) 0.3463(8) 0.053(2) Uiso 0.80 1 d P . . F1D F 1.5778(12) 0.2350(9) 0.3059(11) 0.027(3) Uiso 0.20 1 d P . . F2D F 1.7783(13) 0.2447(10) 0.2889(12) 0.032(3) Uiso 0.20 1 d P . . F3D F 1.4740(16) 0.4149(13) 0.3958(14) 0.040(4) Uiso 0.20 1 d P . . F4D F 1.704(2) 0.2960(16) 0.4344(19) 0.068(5) Uiso 0.20 1 d P . . F5D F 1.706(2) 0.3895(18) 0.435(2) 0.070(6) Uiso 0.20 1 d P . . F6D F 1.5376(8) 0.4793(7) 0.2838(8) 0.0348(18) Uiso 0.40 1 d P . . F7D F 1.5206(15) 0.3328(13) 0.3771(13) 0.032(3) Uiso 0.20 1 d P . . F8D F 1.481(2) 0.4176(19) 0.218(2) 0.029(5) Uiso 0.10 1 d P . . F9D F 1.5641(19) 0.4532(16) 0.3323(18) 0.045(4) Uiso 0.20 1 d P . . F10D F 1.6381(13) 0.4861(12) 0.4374(12) 0.024(3) Uiso 0.20 1 d P . . C11D C 1.663(3) 0.390(2) 0.281(2) 0.032(6) Uiso 0.20 1 d P . . C12D C 1.675(3) 0.284(2) 0.295(3) 0.046(6) Uiso 0.20 1 d P . . C13D C 1.569(2) 0.3690(17) 0.175(2) 0.026(4) Uiso 0.20 1 d P . . 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 0.0409(3) 0.0511(4) 0.0259(3) 0.0060(2) -0.00809(19) 0.0035(2) F1 0.0572(19) 0.0391(16) 0.0272(14) 0.0129(12) 0.0030(13) 0.0062(14) O1 0.0312(18) 0.055(2) 0.0318(18) -0.0009(16) 0.0010(14) -0.0130(16) N1 0.0295(18) 0.0222(17) 0.0205(17) -0.0008(13) -0.0004(14) 0.0001(14) N2 0.0274(18) 0.0236(17) 0.0202(17) 0.0017(13) 0.0016(14) 0.0013(14) C1 0.035(2) 0.026(2) 0.0202(19) -0.0023(16) -0.0014(17) 0.0062(18) C2 0.048(3) 0.023(2) 0.023(2) 0.0044(17) 0.0044(19) 0.0026(19) C3 0.043(3) 0.030(2) 0.030(2) 0.0046(19) 0.007(2) -0.007(2) C4 0.033(2) 0.031(2) 0.026(2) -0.0007(17) 0.0000(18) -0.0041(19) C5 0.031(2) 0.0212(19) 0.0211(19) -0.0007(15) 0.0021(16) -0.0002(16) C6 0.035(2) 0.038(3) 0.026(2) 0.0042(19) 0.0058(19) 0.009(2) C7 0.040(3) 0.037(3) 0.030(2) 0.007(2) 0.001(2) 0.015(2) C8 0.049(3) 0.027(2) 0.022(2) 0.0045(17) 0.0007(19) 0.010(2) C9 0.040(3) 0.027(2) 0.029(2) 0.0054(18) 0.005(2) 0.0017(19) C10 0.029(2) 0.024(2) 0.026(2) 0.0019(17) 0.0008(17) -0.0005(17) C14 0.038(3) 0.051(3) 0.031(3) -0.003(2) -0.008(2) -0.003(2) _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 C1 1.897(5) . ? F1 C2 1.348(5) . ? O1 C4 1.357(6) . ? O1 C14 1.451(6) . ? N1 C1 1.325(6) . ? N1 C5 1.341(6) . ? N2 C5 1.402(5) . ? N2 C10 1.474(6) . ? N2 C6 1.482(6) . ? C1 C2 1.376(7) . ? C2 C3 1.391(7) . ? C3 C4 1.411(7) . ? C3 C11 1.518(9) . ? C4 C5 1.410(6) . ? C6 C7 1.526(6) . ? C7 C8 1.535(7) . ? C8 C9 1.520(7) . ? C9 C10 1.530(6) . ? F2 C11 1.378(9) . ? F3 C12 1.251(8) . ? F4 C12 1.351(8) . ? F5 C12 1.342(9) . ? F6 C13 1.622(13) . ? F7 C13 1.313(10) . ? F8 C13 1.317(12) . ? C11 C13 1.521(13) . ? C11 C12 1.611(10) . ? 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 C4 O1 C14 116.3(4) . . ? C1 N1 C5 119.2(4) . . ? C5 N2 C10 115.0(3) . . ? C5 N2 C6 113.8(3) . . ? C10 N2 C6 112.2(4) . . ? N1 C1 C2 123.5(4) . . ? N1 C1 Br1 117.6(4) . . ? C2 C1 Br1 118.8(3) . . ? F1 C2 C1 118.6(4) . . ? F1 C2 C3 122.2(4) . . ? C1 C2 C3 119.2(4) . . ? C2 C3 C4 117.4(4) . . ? C2 C3 C11 119.3(5) . . ? C4 C3 C11 123.2(5) . . ? O1 C4 C5 122.8(4) . . ? O1 C4 C3 118.0(4) . . ? C5 C4 C3 119.1(4) . . ? N1 C5 N2 118.1(4) . . ? N1 C5 C4 120.8(4) . . ? N2 C5 C4 121.1(4) . . ? N2 C6 C7 110.3(4) . . ? C6 C7 C8 110.8(4) . . ? C9 C8 C7 109.1(4) . . ? C8 C9 C10 111.1(4) . . ? N2 C10 C9 110.6(4) . . ? F2 C11 C3 110.8(6) . . ? F2 C11 C13 104.9(7) . . ? C3 C11 C13 108.9(7) . . ? F2 C11 C12 102.0(6) . . ? C3 C11 C12 115.4(6) . . ? C13 C11 C12 114.1(7) . . ? F3 C12 F5 112.1(6) . . ? F3 C12 F4 111.6(6) . . ? F5 C12 F4 105.5(6) . . ? F3 C12 C11 112.1(6) . . ? F5 C12 C11 106.9(6) . . ? F4 C12 C11 108.4(6) . . ? F7 C13 F8 105.0(8) . . ? F7 C13 C11 110.8(8) . . ? F8 C13 C11 120.2(9) . . ? F7 C13 F6 97.6(7) . . ? F8 C13 F6 104.4(9) . . ? C11 C13 F6 116.2(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.249 _refine_diff_density_min -1.279 _refine_diff_density_rms 0.127 data_s194s _database_code_CSD 167083 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-dibromo-3-fluoro-5-methoxy-4-(1,2,2,2-tetra- fluoro-1-trifluoromethyl-ethyl)-pyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H3 Br2 F8 N O' _chemical_formula_weight 452.94 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 monoclinic _symmetry_space_group_name_H-M 'P 2~1~/c' 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 10.446(2) _cell_length_b 7.122(1) _cell_length_c 17.251(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.71(3) _cell_angle_gamma 90.00 _cell_volume 1280.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 998 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 20.8 _exptl_crystal_description prizm _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 6.424 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.1415 _exptl_absorpt_correction_T_max 0.2859 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD 1K' _diffrn_measurement_method '\w-scan' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12605 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2941 _reflns_number_gt 2346 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0700P)^2^+8.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2941 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 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 1.15636(7) 0.84053(9) 0.81861(4) 0.0480(2) Uani 1 1 d . . . Br2 Br 1.01839(6) 0.69107(7) 1.11249(3) 0.03420(18) Uani 1 1 d . . . N1 N 1.0581(4) 0.7670(6) 0.9602(2) 0.0250(9) Uani 1 1 d . . . O1 O 0.7464(4) 0.7660(6) 1.0415(3) 0.0497(12) Uani 1 1 d . . . C1 C 1.0257(6) 0.8095(7) 0.8871(3) 0.0288(11) Uani 1 1 d . . . C2 C 0.8989(6) 0.8321(7) 0.8604(3) 0.0354(13) Uani 1 1 d . . . C3 C 0.7996(6) 0.8142(8) 0.9095(4) 0.0354(13) Uani 1 1 d . . . C4 C 0.8335(5) 0.7704(7) 0.9872(3) 0.0300(11) Uani 1 1 d . . . C5 C 0.9656(5) 0.7478(7) 1.0081(3) 0.0238(10) Uani 1 1 d . . . C6 C 0.7084(7) 0.5823(10) 1.0685(5) 0.0502(17) Uani 1 1 d . . . H61 H 0.6146 0.5724 1.0641 0.060 Uiso 1 1 calc R . . H62 H 0.7395 0.5660 1.1229 0.060 Uiso 1 1 calc R . . H63 H 0.7453 0.4847 1.0367 0.060 Uiso 1 1 calc R . . F1 F 0.8727(5) 0.8748(6) 0.7854(2) 0.0588(12) Uani 1 1 d . . . F2 F 0.5746(5) 0.7484(8) 0.9412(3) 0.0465(12) Uiso 0.70 1 d P . . F2' F 0.6929(13) 1.003(2) 0.8003(8) 0.051(3) Uiso 0.30 1 d P . . F3 F 0.6832(6) 1.1405(9) 0.8397(4) 0.0544(14) Uiso 0.70 1 d P . . F3' F 0.5214(15) 0.875(2) 0.9558(9) 0.061(4) Uiso 0.30 1 d P . . F4 F 0.5032(7) 1.0887(11) 0.8654(4) 0.0485(19) Uiso 0.70 1 d P . . F4' F 0.4792(13) 1.043(2) 0.8731(7) 0.032(3) Uiso 0.30 1 d P . . F5 F 0.6345(6) 1.0982(9) 0.9653(4) 0.0449(14) Uiso 0.70 1 d P . . F5' F 0.6655(12) 1.1379(17) 0.9464(7) 0.033(3) Uiso 0.30 1 d P . . F6 F 0.4836(6) 0.6867(9) 0.8137(4) 0.0430(15) Uiso 0.70 1 d P . . F6' F 0.4879(12) 0.747(2) 0.7978(7) 0.034(3) Uiso 0.30 1 d P . . F7 F 0.6692(6) 0.5740(9) 0.8031(4) 0.0485(14) Uiso 0.70 1 d P . . F7' F 0.6812(13) 0.636(2) 0.7730(9) 0.049(3) Uiso 0.30 1 d P . . F8 F 0.6220(6) 0.8404(8) 0.7498(3) 0.0526(14) Uiso 0.70 1 d P . . F8' F 0.6122(13) 0.560(2) 0.8842(8) 0.053(3) Uiso 0.30 1 d P . . C7 C 0.6518(8) 0.8315(12) 0.8885(5) 0.0328(18) Uiso 0.70 1 d P . . C7' C 0.6766(18) 0.874(3) 0.8624(11) 0.027(4) Uiso 0.30 1 d P . . C8 C 0.6188(10) 1.0472(14) 0.8861(6) 0.041(2) Uiso 0.70 1 d P . . C8' C 0.5930(17) 1.002(3) 0.9113(10) 0.024(3) Uiso 0.30 1 d P . . C9 C 0.6087(7) 0.7308(11) 0.8149(4) 0.0478(16) 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 0.0630(5) 0.0414(4) 0.0420(4) 0.0014(3) 0.0214(3) -0.0042(3) Br2 0.0536(4) 0.0230(3) 0.0250(3) -0.0010(2) -0.0051(2) 0.0010(2) N1 0.027(2) 0.0175(19) 0.030(2) -0.0018(16) -0.0026(17) 0.0012(16) O1 0.039(2) 0.030(2) 0.083(4) -0.001(2) 0.027(2) 0.0069(19) C1 0.040(3) 0.019(2) 0.028(2) -0.002(2) 0.004(2) -0.001(2) C2 0.053(4) 0.023(3) 0.029(3) -0.003(2) -0.012(2) 0.012(2) C3 0.034(3) 0.027(3) 0.044(3) -0.013(2) -0.013(2) 0.010(2) C4 0.027(3) 0.016(2) 0.046(3) -0.006(2) 0.001(2) 0.0038(19) C5 0.029(3) 0.015(2) 0.026(2) -0.0015(18) -0.0047(19) 0.0017(18) C6 0.040(4) 0.042(4) 0.071(5) 0.011(3) 0.019(3) 0.006(3) F1 0.095(3) 0.047(2) 0.0306(19) -0.0002(17) -0.0186(19) 0.022(2) _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 C1 1.875(6) . ? Br2 C5 1.893(5) . ? N1 C5 1.318(7) . ? N1 C1 1.319(7) . ? O1 C4 1.347(7) . ? O1 C6 1.453(8) . ? C1 C2 1.383(8) . ? C2 F1 1.340(6) . ? C2 C3 1.388(9) . ? C3 C4 1.399(8) . ? C3 C7' 1.53(2) . ? C3 C7 1.57(1) . ? C4 C5 1.412(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 C5 N1 C1 118.0(5) . . ? C4 O1 C6 117.1(5) . . ? N1 C1 C2 121.7(5) . . ? N1 C1 Br1 118.5(4) . . ? C2 C1 Br1 119.8(4) . . ? F1 C2 C1 118.7(6) . . ? F1 C2 C3 119.8(5) . . ? C1 C2 C3 121.6(5) . . ? C2 C3 C4 116.9(5) . . ? O1 C4 C3 122.0(5) . . ? O1 C4 C5 120.9(5) . . ? C3 C4 C5 116.9(5) . . ? N1 C5 C4 124.9(5) . . ? N1 C5 Br2 116.0(4) . . ? C4 C5 Br2 119.1(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.341 _refine_diff_density_min -1.793 _refine_diff_density_rms 0.139