# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_pf6 _database_code_depnum_ccdc_archive 'CCDC 879092' #TrackingRef 'Salts 1-4 KMLee.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 F6 N3 O2 P' _chemical_formula_weight 325.16 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_hall '-P 2ybc' 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 8.8952(8) _cell_length_b 12.8953(12) _cell_length_c 11.1052(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.686(2) _cell_angle_gamma 90.00 _cell_volume 1265.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2838 _cell_measurement_theta_min 3.1595 _cell_measurement_theta_max 26.4939 _exptl_crystal_description Tabullar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8782 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10317 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2606 _reflns_number_gt 2064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0435P)^2^+0.8641P] 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 2606 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.41996(6) 0.17028(4) 0.78031(5) 0.02084(15) Uani 1 1 d . . . F1 F 0.24077(13) 0.17880(11) 0.75172(11) 0.0339(3) Uani 1 1 d . . . F2 F 0.40381(13) 0.16606(10) 0.92273(11) 0.0279(3) Uani 1 1 d . . . F3 F 0.40691(16) 0.04667(10) 0.77394(13) 0.0378(4) Uani 1 1 d . . . F4 F 0.43588(13) 0.17300(10) 0.63766(11) 0.0320(3) Uani 1 1 d . . . F5 F 0.60003(13) 0.16208(10) 0.80964(11) 0.0313(3) Uani 1 1 d . . . F6 F 0.43379(15) 0.29323(10) 0.78685(13) 0.0385(3) Uani 1 1 d . . . O1 O 0.95986(15) 0.35488(10) 0.50955(13) 0.0212(3) Uani 1 1 d . . . O2 O 1.03609(15) -0.11963(10) 0.67705(13) 0.0229(3) Uani 1 1 d . . . N3 N 0.85722(19) -0.17007(12) 0.52890(15) 0.0196(4) Uani 1 1 d . . . H3B H 0.8956 -0.2328 0.5257 0.023 Uiso 1 1 calc R . . H3A H 0.7756 -0.1531 0.4804 0.023 Uiso 1 1 calc R . . N2 N 0.77321(16) 0.21205(11) 0.59981(14) 0.0130(3) Uani 1 1 d . . . N1 N 0.80487(18) 0.48954(12) 0.53500(16) 0.0215(4) Uani 1 1 d . . . H1B H 0.8645 0.5344 0.5043 0.026 Uiso 1 1 calc R . . H1A H 0.7199 0.5106 0.5604 0.026 Uiso 1 1 calc R . . C3 C 0.9223(2) -0.10128(13) 0.60682(17) 0.0151(4) Uani 1 1 d . . . C6 C 0.85775(19) 0.00752(13) 0.60342(17) 0.0135(4) Uani 1 1 d . . . C7 C 0.7489(2) 0.04436(14) 0.51399(18) 0.0174(4) Uani 1 1 d . . . H7 H 0.7026 -0.0011 0.4534 0.021 Uiso 1 1 calc R . . C8 C 0.7086(2) 0.14752(14) 0.51391(18) 0.0169(4) Uani 1 1 d . . . H8 H 0.6345 0.1732 0.4527 0.020 Uiso 1 1 calc R . . C2 C 0.7289(2) 0.32224(13) 0.59891(18) 0.0151(4) Uani 1 1 d . . . H2A H 0.7216 0.3454 0.6830 0.018 Uiso 1 1 calc R . . H2B H 0.6280 0.3304 0.5520 0.018 Uiso 1 1 calc R . . C1 C 0.8431(2) 0.39016(14) 0.54302(17) 0.0150(4) Uani 1 1 d . . . C4 C 0.8780(2) 0.17816(14) 0.68804(18) 0.0169(4) Uani 1 1 d . . . H4 H 0.9220 0.2250 0.7481 0.020 Uiso 1 1 calc R . . C5 C 0.9215(2) 0.07568(14) 0.69142(18) 0.0170(4) Uani 1 1 d . . . H5 H 0.9952 0.0517 0.7540 0.020 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 P1 0.0174(3) 0.0280(3) 0.0169(3) -0.0013(2) 0.0010(2) -0.0078(2) F1 0.0181(6) 0.0566(9) 0.0262(7) -0.0069(6) -0.0010(5) -0.0054(6) F2 0.0236(6) 0.0415(7) 0.0188(7) -0.0051(5) 0.0031(5) -0.0080(5) F3 0.0497(9) 0.0271(7) 0.0392(9) -0.0058(6) 0.0155(7) -0.0068(6) F4 0.0239(6) 0.0541(9) 0.0179(7) 0.0015(6) 0.0016(5) -0.0089(6) F5 0.0180(6) 0.0532(9) 0.0227(7) 0.0034(6) 0.0019(5) -0.0019(5) F6 0.0441(8) 0.0280(7) 0.0420(9) 0.0016(6) -0.0006(7) -0.0090(6) O1 0.0209(7) 0.0125(6) 0.0320(9) 0.0013(6) 0.0106(6) 0.0024(5) O2 0.0241(7) 0.0152(7) 0.0266(8) 0.0020(6) -0.0082(6) 0.0034(5) N3 0.0236(8) 0.0116(8) 0.0220(9) -0.0020(6) -0.0033(7) 0.0042(6) N2 0.0118(7) 0.0115(7) 0.0157(8) 0.0005(6) 0.0016(6) 0.0003(6) N1 0.0196(8) 0.0114(8) 0.0348(11) 0.0022(7) 0.0082(7) 0.0022(6) C3 0.0168(9) 0.0120(9) 0.0167(10) 0.0038(7) 0.0028(8) 0.0002(7) C6 0.0133(8) 0.0122(8) 0.0152(10) 0.0008(7) 0.0031(7) -0.0017(7) C7 0.0209(9) 0.0137(9) 0.0166(10) -0.0016(7) -0.0024(8) -0.0006(7) C8 0.0177(9) 0.0167(9) 0.0152(10) 0.0010(7) -0.0025(7) 0.0008(7) C2 0.0151(8) 0.0106(8) 0.0194(10) -0.0001(7) 0.0018(7) 0.0016(7) C1 0.0174(9) 0.0123(9) 0.0149(10) -0.0014(7) 0.0001(7) 0.0008(7) C4 0.0158(9) 0.0150(9) 0.0185(10) -0.0019(7) -0.0036(7) -0.0018(7) C5 0.0162(9) 0.0160(9) 0.0176(10) 0.0023(7) -0.0031(7) 0.0002(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F6 1.5912(14) . ? P1 F1 1.5923(12) . ? P1 F3 1.5992(14) . ? P1 F5 1.6005(12) . ? P1 F2 1.6056(13) . ? P1 F4 1.6072(13) . ? O1 C1 1.230(2) . ? O2 C3 1.226(2) . ? N3 C3 1.325(2) . ? N3 H3B 0.8800 . ? N3 H3A 0.8800 . ? N2 C8 1.344(2) . ? N2 C4 1.344(2) . ? N2 C2 1.474(2) . ? N1 C1 1.326(2) . ? N1 H1B 0.8800 . ? N1 H1A 0.8800 . ? C3 C6 1.515(2) . ? C6 C5 1.386(3) . ? C6 C7 1.388(3) . ? C7 C8 1.378(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C2 C1 1.526(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F6 P1 F1 90.61(8) . . ? F6 P1 F3 179.73(9) . . ? F1 P1 F3 89.66(8) . . ? F6 P1 F5 89.22(7) . . ? F1 P1 F5 179.71(8) . . ? F3 P1 F5 90.51(7) . . ? F6 P1 F2 90.24(7) . . ? F1 P1 F2 89.80(7) . . ? F3 P1 F2 89.73(7) . . ? F5 P1 F2 89.97(7) . . ? F6 P1 F4 90.46(7) . . ? F1 P1 F4 90.17(7) . . ? F3 P1 F4 89.57(7) . . ? F5 P1 F4 90.06(7) . . ? F2 P1 F4 179.30(8) . . ? C3 N3 H3B 120.0 . . ? C3 N3 H3A 120.0 . . ? H3B N3 H3A 120.0 . . ? C8 N2 C4 121.28(15) . . ? C8 N2 C2 120.02(15) . . ? C4 N2 C2 118.71(15) . . ? C1 N1 H1B 120.0 . . ? C1 N1 H1A 120.0 . . ? H1B N1 H1A 120.0 . . ? O2 C3 N3 123.49(17) . . ? O2 C3 C6 118.49(16) . . ? N3 C3 C6 117.92(16) . . ? C5 C6 C7 118.81(16) . . ? C5 C6 C3 116.54(16) . . ? C7 C6 C3 124.47(17) . . ? C8 C7 C6 119.41(17) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? N2 C8 C7 120.50(18) . . ? N2 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? N2 C2 C1 111.46(14) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? O1 C1 N1 123.77(17) . . ? O1 C1 C2 122.39(16) . . ? N1 C1 C2 113.84(15) . . ? N2 C4 C5 120.07(17) . . ? N2 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.93(17) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.530 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.056 data_otf _database_code_depnum_ccdc_archive 'CCDC 879093' #TrackingRef 'Salts 1-4 KMLee.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 F3 N3 O5 S' _chemical_formula_weight 329.26 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6815(4) _cell_length_b 12.4142(5) _cell_length_c 18.5652(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.7840(10) _cell_angle_gamma 90.00 _cell_volume 2644.71(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5238 _cell_measurement_theta_min 2.4170 _cell_measurement_theta_max 26.1898 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8345 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 16.6666 _diffrn_reflns_number 20963 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.44 _reflns_number_total 5447 _reflns_number_gt 4359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0395P)^2^+1.3879P] 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 5447 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C31 C 0.26545(16) 0.20296(16) 0.06241(11) 0.0238(4) Uani 1 1 d . . . C32 C 0.26674(18) 0.70910(18) 0.92889(11) 0.0301(5) Uani 1 1 d . . . C28 C 0.21066(14) 0.83083(15) 0.16868(10) 0.0168(4) Uani 1 1 d . . . H28 H 0.2800 0.7894 0.1803 0.020 Uiso 1 1 calc R . . C27 C 0.20931(14) 0.93533(15) 0.19205(10) 0.0171(4) Uani 1 1 d . . . H27 H 0.2775 0.9660 0.2206 0.020 Uiso 1 1 calc R . . C26 C 0.10863(14) 0.99660(14) 0.17419(9) 0.0146(4) Uani 1 1 d . . . C25 C 0.01134(15) 0.95130(14) 0.13005(10) 0.0166(4) Uani 1 1 d . . . H25 H -0.0570 0.9930 0.1144 0.020 Uiso 1 1 calc R . . C24 C 0.01540(15) 0.84510(15) 0.10930(10) 0.0175(4) Uani 1 1 d . . . H24 H -0.0517 0.8127 0.0806 0.021 Uiso 1 1 calc R . . C22 C 0.11052(15) 0.67176(14) 0.10997(10) 0.0164(4) Uani 1 1 d . . . H22B H 0.1904 0.6469 0.1079 0.020 Uiso 1 1 calc R . . H22A H 0.0612 0.6608 0.0610 0.020 Uiso 1 1 calc R . . C21 C 0.06199(14) 0.60626(14) 0.16710(10) 0.0161(4) Uani 1 1 d . . . C23 C 0.10517(14) 1.10467(14) 0.21079(10) 0.0162(4) Uani 1 1 d . . . C8 C 0.98291(16) 0.16780(16) 0.39632(11) 0.0239(4) Uani 1 1 d . . . H8 H 1.0364 0.1961 0.4368 0.029 Uiso 1 1 calc R . . C7 C 0.99165(16) 0.06193(15) 0.37669(11) 0.0243(4) Uani 1 1 d . . . H7 H 1.0501 0.0170 0.4038 0.029 Uiso 1 1 calc R . . C6 C 0.91463(14) 0.02114(14) 0.31705(10) 0.0144(4) Uani 1 1 d . . . C5 C 0.82676(16) 0.08757(16) 0.28226(11) 0.0250(4) Uani 1 1 d . . . H5 H 0.7703 0.0604 0.2429 0.030 Uiso 1 1 calc R . . C4 C 0.82043(17) 0.19242(16) 0.30411(11) 0.0258(4) Uani 1 1 d . . . H4 H 0.7593 0.2375 0.2801 0.031 Uiso 1 1 calc R . . C2 C 0.89911(15) 0.34728(14) 0.37649(10) 0.0157(4) Uani 1 1 d . . . H2A H 0.9424 0.3598 0.4269 0.019 Uiso 1 1 calc R . . H2B H 0.8178 0.3718 0.3740 0.019 Uiso 1 1 calc R . . C1 C 0.95541(14) 0.41182(14) 0.32206(10) 0.0153(4) Uani 1 1 d . . . C3 C 0.92291(14) -0.08888(14) 0.28425(10) 0.0160(4) Uani 1 1 d . . . F1 F 0.27864(10) 0.20423(10) 0.13519(6) 0.0295(3) Uani 1 1 d . . . F2 F 0.19031(12) 0.12466(10) 0.03750(8) 0.0423(3) Uani 1 1 d . . . F3 F 0.36878(11) 0.17678(12) 0.04664(7) 0.0428(3) Uani 1 1 d . . . F4 F 0.24156(15) 0.63221(11) 0.97276(8) 0.0541(4) Uani 1 1 d . . . F5 F 0.20031(11) 0.69495(11) 0.86312(7) 0.0413(3) Uani 1 1 d . . . F6 F 0.37720(11) 0.69434(14) 0.92205(8) 0.0530(4) Uani 1 1 d . . . N22 N 0.11291(12) 0.78686(11) 0.12907(8) 0.0144(3) Uani 1 1 d . . . N21 N 0.04958(13) 0.50191(12) 0.15245(9) 0.0205(3) Uani 1 1 d . . . H21B H 0.0224 0.4589 0.1830 0.025 Uiso 1 1 calc R . . H21A H 0.0685 0.4757 0.1122 0.025 Uiso 1 1 calc R . . N23 N 0.02902(13) 1.17695(12) 0.17722(9) 0.0203(3) Uani 1 1 d . . . H23B H 0.0212 1.2393 0.1983 0.024 Uiso 1 1 calc R . . H23A H -0.0134 1.1623 0.1340 0.024 Uiso 1 1 calc R . . N2 N 0.90004(12) 0.23172(11) 0.35925(8) 0.0139(3) Uani 1 1 d . . . N1 N 0.95376(13) 0.51709(12) 0.33171(8) 0.0187(3) Uani 1 1 d . . . H1B H 0.9849 0.5601 0.3030 0.022 Uiso 1 1 calc R . . H1A H 0.9215 0.5443 0.3669 0.022 Uiso 1 1 calc R . . N3 N 1.01984(13) -0.14526(12) 0.30657(8) 0.0185(3) Uani 1 1 d . . . H3B H 1.0291 -0.2081 0.2865 0.022 Uiso 1 1 calc R . . H3A H 1.0747 -0.1197 0.3414 0.022 Uiso 1 1 calc R . . O5 O 0.21227(11) 0.31455(12) -0.05519(7) 0.0278(3) Uani 1 1 d . . . O4 O 0.30522(14) 0.40508(12) 0.05736(9) 0.0420(4) Uani 1 1 d . . . O3 O 0.10390(12) 0.34810(12) 0.04146(8) 0.0313(3) Uani 1 1 d . . . O25 O 0.12571(11) 0.84387(11) 0.97047(7) 0.0226(3) Uani 1 1 d . . . O24 O 0.32633(12) 0.84022(13) 1.03588(8) 0.0311(3) Uani 1 1 d . . . O23 O 0.27817(13) 0.91475(13) 0.91221(8) 0.0358(4) Uani 1 1 d . . . O21 O 0.03756(11) 0.64933(10) 0.22224(7) 0.0210(3) Uani 1 1 d . . . O22 O 0.16765(11) 1.11863(10) 0.27105(7) 0.0221(3) Uani 1 1 d . . . O1 O 0.99860(11) 0.36658(10) 0.27434(7) 0.0190(3) Uani 1 1 d . . . O2 O 0.84296(11) -0.11980(10) 0.23590(7) 0.0216(3) Uani 1 1 d . . . S1 S 0.21631(4) 0.33285(4) 0.02164(3) 0.01975(12) Uani 1 1 d . . . S2 S 0.24771(4) 0.84229(4) 0.96647(3) 0.02001(12) 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 C31 0.0229(9) 0.0259(10) 0.0213(10) -0.0007(8) 0.0007(8) -0.0034(8) C32 0.0303(11) 0.0417(13) 0.0185(10) 0.0014(9) 0.0050(8) 0.0130(9) C28 0.0138(8) 0.0191(9) 0.0174(9) 0.0011(8) 0.0026(7) 0.0005(7) C27 0.0133(8) 0.0181(9) 0.0190(9) -0.0008(7) 0.0010(7) -0.0022(7) C26 0.0164(8) 0.0150(9) 0.0129(9) 0.0026(7) 0.0046(7) -0.0016(7) C25 0.0159(8) 0.0170(9) 0.0159(9) 0.0023(7) 0.0002(7) 0.0019(7) C24 0.0160(8) 0.0194(9) 0.0156(9) 0.0014(8) -0.0011(7) -0.0012(7) C22 0.0200(8) 0.0144(9) 0.0145(9) -0.0008(7) 0.0025(7) 0.0000(7) C21 0.0158(8) 0.0164(9) 0.0158(9) -0.0001(7) 0.0023(7) -0.0007(7) C23 0.0160(8) 0.0172(9) 0.0167(9) 0.0011(7) 0.0066(7) -0.0030(7) C8 0.0218(9) 0.0211(10) 0.0243(10) -0.0048(8) -0.0070(8) 0.0041(8) C7 0.0229(9) 0.0180(10) 0.0278(11) -0.0021(8) -0.0063(8) 0.0067(8) C6 0.0137(8) 0.0145(9) 0.0156(9) 0.0021(7) 0.0039(6) -0.0024(6) C5 0.0228(9) 0.0187(10) 0.0283(11) -0.0041(8) -0.0091(8) 0.0024(8) C4 0.0228(9) 0.0211(10) 0.0284(11) -0.0023(9) -0.0085(8) 0.0059(8) C2 0.0184(8) 0.0123(8) 0.0170(9) -0.0016(7) 0.0046(7) 0.0010(7) C1 0.0120(7) 0.0156(9) 0.0175(9) -0.0005(7) 0.0007(7) 0.0010(7) C3 0.0171(8) 0.0138(9) 0.0175(9) 0.0023(7) 0.0044(7) -0.0028(7) F1 0.0295(6) 0.0380(7) 0.0199(6) 0.0062(5) 0.0015(5) -0.0086(5) F2 0.0542(8) 0.0214(6) 0.0427(8) 0.0008(6) -0.0130(6) -0.0116(6) F3 0.0361(7) 0.0570(9) 0.0365(8) 0.0081(7) 0.0103(6) 0.0222(6) F4 0.0963(12) 0.0265(7) 0.0456(9) 0.0072(6) 0.0292(9) 0.0165(8) F5 0.0432(7) 0.0491(8) 0.0277(7) -0.0116(6) -0.0029(6) 0.0117(6) F6 0.0352(7) 0.0840(12) 0.0402(8) -0.0167(8) 0.0078(6) 0.0290(7) N22 0.0175(7) 0.0138(7) 0.0120(7) 0.0010(6) 0.0031(6) -0.0020(6) N21 0.0299(8) 0.0144(8) 0.0191(8) -0.0019(7) 0.0097(7) -0.0024(6) N23 0.0202(7) 0.0153(8) 0.0241(9) -0.0039(7) 0.0008(6) 0.0031(6) N2 0.0150(7) 0.0127(7) 0.0142(7) 0.0006(6) 0.0036(6) 0.0003(6) N1 0.0257(8) 0.0133(8) 0.0197(8) -0.0014(6) 0.0110(6) -0.0010(6) N3 0.0227(8) 0.0140(8) 0.0181(8) -0.0022(6) 0.0019(6) 0.0025(6) O5 0.0263(7) 0.0393(9) 0.0178(7) 0.0038(6) 0.0043(6) -0.0004(6) O4 0.0459(9) 0.0306(9) 0.0389(9) 0.0084(7) -0.0190(7) -0.0218(7) O3 0.0295(7) 0.0387(9) 0.0262(8) -0.0062(7) 0.0061(6) 0.0079(6) O25 0.0191(6) 0.0269(7) 0.0222(7) 0.0021(6) 0.0051(5) 0.0038(5) O24 0.0244(7) 0.0449(9) 0.0218(8) -0.0026(7) -0.0012(6) 0.0084(6) O23 0.0351(8) 0.0433(9) 0.0318(9) 0.0128(7) 0.0136(7) -0.0044(7) O21 0.0318(7) 0.0149(6) 0.0181(7) -0.0018(5) 0.0093(6) -0.0022(5) O22 0.0257(7) 0.0192(7) 0.0194(7) -0.0031(6) -0.0011(6) -0.0022(5) O1 0.0232(6) 0.0151(6) 0.0209(7) -0.0011(5) 0.0096(5) 0.0015(5) O2 0.0201(6) 0.0178(7) 0.0254(7) -0.0042(6) 0.0007(5) -0.0033(5) S1 0.0196(2) 0.0201(2) 0.0179(2) -0.00141(19) -0.00077(17) -0.00539(18) S2 0.0177(2) 0.0264(3) 0.0164(2) 0.0045(2) 0.00434(17) 0.00245(18) _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 C31 F1 1.331(2) . ? C31 F2 1.333(2) . ? C31 F3 1.334(2) . ? C31 S1 1.828(2) . ? C32 F4 1.323(3) . ? C32 F5 1.330(2) . ? C32 F6 1.333(2) . ? C32 S2 1.824(2) . ? C28 N22 1.352(2) . ? C28 C27 1.369(3) . ? C28 H28 0.9500 . ? C27 C26 1.388(2) . ? C27 H27 0.9500 . ? C26 C25 1.389(2) . ? C26 C23 1.508(2) . ? C25 C24 1.377(3) . ? C25 H25 0.9500 . ? C24 N22 1.341(2) . ? C24 H24 0.9500 . ? C22 N22 1.471(2) . ? C22 C21 1.527(2) . ? C22 H22B 0.9900 . ? C22 H22A 0.9900 . ? C21 O21 1.235(2) . ? C21 N21 1.326(2) . ? C23 O22 1.228(2) . ? C23 N23 1.333(2) . ? C8 N2 1.338(2) . ? C8 C7 1.373(3) . ? C8 H8 0.9500 . ? C7 C6 1.385(3) . ? C7 H7 0.9500 . ? C6 C5 1.379(2) . ? C6 C3 1.506(2) . ? C5 C4 1.370(3) . ? C5 H5 0.9500 . ? C4 N2 1.340(2) . ? C4 H4 0.9500 . ? C2 N2 1.470(2) . ? C2 C1 1.531(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 O1 1.234(2) . ? C1 N1 1.320(2) . ? C3 O2 1.229(2) . ? C3 N3 1.330(2) . ? N21 H21B 0.8800 . ? N21 H21A 0.8800 . ? N23 H23B 0.8800 . ? N23 H23A 0.8800 . ? N1 H1B 0.8800 . ? N1 H1A 0.8800 . ? N3 H3B 0.8800 . ? N3 H3A 0.8800 . ? O5 S1 1.4363(14) . ? O4 S1 1.4370(14) . ? O3 S1 1.4410(14) . ? O25 S2 1.4410(13) . ? O24 S2 1.4360(14) . ? O23 S2 1.4439(15) . ? 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 F1 C31 F2 107.72(16) . . ? F1 C31 F3 106.74(15) . . ? F2 C31 F3 108.08(17) . . ? F1 C31 S1 112.19(14) . . ? F2 C31 S1 111.36(13) . . ? F3 C31 S1 110.54(14) . . ? F4 C32 F5 108.12(19) . . ? F4 C32 F6 106.87(18) . . ? F5 C32 F6 107.66(16) . . ? F4 C32 S2 111.19(14) . . ? F5 C32 S2 112.26(14) . . ? F6 C32 S2 110.52(16) . . ? N22 C28 C27 119.76(16) . . ? N22 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C27 C26 120.21(16) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C26 C25 118.83(16) . . ? C27 C26 C23 118.22(15) . . ? C25 C26 C23 122.54(15) . . ? C24 C25 C26 119.04(16) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? N22 C24 C25 120.77(16) . . ? N22 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? N22 C22 C21 110.03(14) . . ? N22 C22 H22B 109.7 . . ? C21 C22 H22B 109.7 . . ? N22 C22 H22A 109.7 . . ? C21 C22 H22A 109.7 . . ? H22B C22 H22A 108.2 . . ? O21 C21 N21 124.03(17) . . ? O21 C21 C22 121.24(16) . . ? N21 C21 C22 114.73(15) . . ? O22 C23 N23 124.17(17) . . ? O22 C23 C26 118.33(16) . . ? N23 C23 C26 117.38(15) . . ? N2 C8 C7 120.91(17) . . ? N2 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C7 C6 119.52(17) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C5 C6 C7 118.09(17) . . ? C5 C6 C3 116.83(16) . . ? C7 C6 C3 124.99(16) . . ? C4 C5 C6 120.41(17) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N2 C4 C5 120.28(17) . . ? N2 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N2 C2 C1 110.20(14) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O1 C1 N1 124.51(17) . . ? O1 C1 C2 121.30(15) . . ? N1 C1 C2 114.19(15) . . ? O2 C3 N3 123.33(17) . . ? O2 C3 C6 118.74(15) . . ? N3 C3 C6 117.83(15) . . ? C24 N22 C28 121.25(15) . . ? C24 N22 C22 118.74(14) . . ? C28 N22 C22 119.95(14) . . ? C21 N21 H21B 120.0 . . ? C21 N21 H21A 120.0 . . ? H21B N21 H21A 120.0 . . ? C23 N23 H23B 120.0 . . ? C23 N23 H23A 120.0 . . ? H23B N23 H23A 120.0 . . ? C8 N2 C4 120.59(16) . . ? C8 N2 C2 120.05(15) . . ? C4 N2 C2 119.29(15) . . ? C1 N1 H1B 120.0 . . ? C1 N1 H1A 120.0 . . ? H1B N1 H1A 120.0 . . ? C3 N3 H3B 120.0 . . ? C3 N3 H3A 120.0 . . ? H3B N3 H3A 120.0 . . ? O5 S1 O4 116.33(10) . . ? O5 S1 O3 114.34(8) . . ? O4 S1 O3 114.50(10) . . ? O5 S1 C31 102.78(9) . . ? O4 S1 C31 102.45(9) . . ? O3 S1 C31 103.93(9) . . ? O24 S2 O25 115.26(8) . . ? O24 S2 O23 115.94(10) . . ? O25 S2 O23 113.74(9) . . ? O24 S2 C32 102.93(9) . . ? O25 S2 C32 102.97(9) . . ? O23 S2 C32 103.55(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.424 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.053 data_bph4 _database_code_depnum_ccdc_archive 'CCDC 879094' #TrackingRef 'Salts 1-4 KMLee.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 B N3 O2' _chemical_formula_weight 499.40 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 9.8176(5) _cell_length_b 17.2416(7) _cell_length_c 30.5102(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5164.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4949 _cell_measurement_theta_min 3.1166 _cell_measurement_theta_max 24.9634 _exptl_crystal_description Lump _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8824 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 40108 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 26.41 _reflns_number_total 5298 _reflns_number_gt 4099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.1111P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5298 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1697 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.003 _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 B1 B 0.3548(2) 0.24937(12) 0.37411(6) 0.0137(4) Uani 1 1 d . . . O1 O 0.41188(13) 0.08345(8) 0.72027(4) 0.0253(3) Uani 1 1 d . . . O2 O 0.12692(13) 0.06893(7) 0.52039(4) 0.0226(3) Uani 1 1 d . . . N1 N 0.63316(16) 0.09522(9) 0.74030(5) 0.0220(4) Uani 1 1 d . . . H1B H 0.6132 0.1114 0.7669 0.026 Uiso 1 1 calc R . . H1A H 0.7188 0.0902 0.7323 0.026 Uiso 1 1 calc R . . N2 N 0.47329(14) 0.03893(8) 0.63649(5) 0.0142(3) Uani 1 1 d . . . N3 N 0.10419(16) -0.05825(9) 0.53682(5) 0.0207(4) Uani 1 1 d . . . H3B H 0.0423 -0.0659 0.5164 0.025 Uiso 1 1 calc R . . H3A H 0.1305 -0.0970 0.5536 0.025 Uiso 1 1 calc R . . C1 C 0.53353(18) 0.07827(10) 0.71213(6) 0.0177(4) Uani 1 1 d . . . C2 C 0.58507(17) 0.04932(10) 0.66800(6) 0.0160(4) Uani 1 1 d . . . H2A H 0.6515 0.0870 0.6560 0.019 Uiso 1 1 calc R . . H2B H 0.6327 -0.0007 0.6721 0.019 Uiso 1 1 calc R . . C3 C 0.15798(17) 0.01186(10) 0.54234(6) 0.0162(4) Uani 1 1 d . . . C4 C 0.46024(18) 0.08950(10) 0.60326(6) 0.0162(4) Uani 1 1 d . . . H4 H 0.5230 0.1311 0.6004 0.019 Uiso 1 1 calc R . . C5 C 0.35670(18) 0.08135(10) 0.57340(6) 0.0168(4) Uani 1 1 d . . . H5 H 0.3470 0.1176 0.5501 0.020 Uiso 1 1 calc R . . C6 C 0.26584(18) 0.01973(10) 0.57736(6) 0.0159(4) Uani 1 1 d . . . C7 C 0.28062(18) -0.03081(10) 0.61245(6) 0.0185(4) Uani 1 1 d . . . H7 H 0.2185 -0.0726 0.6162 0.022 Uiso 1 1 calc R . . C8 C 0.38511(19) -0.02033(10) 0.64172(6) 0.0191(4) Uani 1 1 d . . . H8 H 0.3954 -0.0549 0.6657 0.023 Uiso 1 1 calc R . . C11 C 0.18843(18) 0.23769(9) 0.37750(6) 0.0139(4) Uani 1 1 d . . . C12 C 0.12240(18) 0.22723(10) 0.41787(6) 0.0168(4) Uani 1 1 d . . . H12 H 0.1762 0.2219 0.4436 0.020 Uiso 1 1 calc R . . C13 C -0.01872(19) 0.22434(10) 0.42173(7) 0.0208(4) Uani 1 1 d . . . H13 H -0.0592 0.2190 0.4498 0.025 Uiso 1 1 calc R . . C14 C -0.10027(19) 0.22920(11) 0.38494(7) 0.0223(4) Uani 1 1 d . . . H14 H -0.1965 0.2253 0.3873 0.027 Uiso 1 1 calc R . . C15 C -0.03902(18) 0.23984(11) 0.34446(7) 0.0218(4) Uani 1 1 d . . . H15 H -0.0936 0.2435 0.3188 0.026 Uiso 1 1 calc R . . C16 C 0.10209(18) 0.24524(10) 0.34114(6) 0.0172(4) Uani 1 1 d . . . H16 H 0.1414 0.2544 0.3132 0.021 Uiso 1 1 calc R . . C21 C 0.42180(17) 0.20757(9) 0.33091(6) 0.0137(4) Uani 1 1 d . . . C22 C 0.35648(17) 0.15101(10) 0.30585(6) 0.0155(4) Uani 1 1 d . . . H22 H 0.2666 0.1361 0.3137 0.019 Uiso 1 1 calc R . . C23 C 0.41746(18) 0.11548(10) 0.26978(6) 0.0173(4) Uani 1 1 d . . . H23 H 0.3685 0.0780 0.2533 0.021 Uiso 1 1 calc R . . C24 C 0.54899(19) 0.13478(10) 0.25805(6) 0.0192(4) Uani 1 1 d . . . H24 H 0.5909 0.1110 0.2334 0.023 Uiso 1 1 calc R . . C25 C 0.61916(18) 0.18921(10) 0.28267(6) 0.0187(4) Uani 1 1 d . . . H25 H 0.7101 0.2025 0.2752 0.022 Uiso 1 1 calc R . . C26 C 0.55680(17) 0.22429(10) 0.31824(6) 0.0166(4) Uani 1 1 d . . . H26 H 0.6071 0.2611 0.3348 0.020 Uiso 1 1 calc R . . C31 C 0.37658(17) 0.34413(10) 0.37268(6) 0.0151(4) Uani 1 1 d . . . C32 C 0.34677(17) 0.38978(10) 0.40968(6) 0.0174(4) Uani 1 1 d . . . H32 H 0.3186 0.3646 0.4359 0.021 Uiso 1 1 calc R . . C33 C 0.35678(18) 0.47008(11) 0.40953(6) 0.0206(4) Uani 1 1 d . . . H33 H 0.3343 0.4985 0.4352 0.025 Uiso 1 1 calc R . . C34 C 0.39927(18) 0.50932(11) 0.37218(6) 0.0211(4) Uani 1 1 d . . . H34 H 0.4087 0.5642 0.3722 0.025 Uiso 1 1 calc R . . C35 C 0.42771(18) 0.46644(10) 0.33474(7) 0.0208(4) Uani 1 1 d . . . H35 H 0.4559 0.4921 0.3087 0.025 Uiso 1 1 calc R . . C36 C 0.41493(17) 0.38562(10) 0.33524(6) 0.0176(4) Uani 1 1 d . . . H36 H 0.4331 0.3577 0.3090 0.021 Uiso 1 1 calc R . . C41 C 0.43344(17) 0.20982(10) 0.41561(6) 0.0148(4) Uani 1 1 d . . . C42 C 0.39976(18) 0.13436(10) 0.42917(6) 0.0185(4) Uani 1 1 d . . . H42 H 0.3269 0.1084 0.4149 0.022 Uiso 1 1 calc R . . C43 C 0.46822(19) 0.09615(11) 0.46247(6) 0.0225(4) Uani 1 1 d . . . H43 H 0.4406 0.0456 0.4710 0.027 Uiso 1 1 calc R . . C44 C 0.57697(19) 0.13171(11) 0.48330(6) 0.0240(5) Uani 1 1 d . . . H44 H 0.6247 0.1057 0.5061 0.029 Uiso 1 1 calc R . . C45 C 0.61526(18) 0.20572(11) 0.47050(6) 0.0218(4) Uani 1 1 d . . . H45 H 0.6902 0.2305 0.4843 0.026 Uiso 1 1 calc R . . C46 C 0.54410(17) 0.24364(11) 0.43748(6) 0.0175(4) Uani 1 1 d . . . H46 H 0.5715 0.2945 0.4294 0.021 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 0.0135(10) 0.0157(10) 0.0119(10) -0.0010(8) 0.0000(7) -0.0008(7) O1 0.0164(7) 0.0385(8) 0.0209(7) -0.0047(6) 0.0010(6) 0.0001(6) O2 0.0234(7) 0.0199(7) 0.0244(8) 0.0037(6) -0.0060(6) -0.0030(5) N1 0.0175(8) 0.0319(9) 0.0168(8) -0.0038(7) 0.0001(6) -0.0018(6) N2 0.0138(7) 0.0139(8) 0.0150(8) 0.0003(6) 0.0005(6) 0.0003(6) N3 0.0223(8) 0.0167(8) 0.0232(9) 0.0012(7) -0.0083(7) 0.0002(6) C1 0.0179(9) 0.0172(9) 0.0181(10) 0.0010(8) -0.0003(7) -0.0005(7) C2 0.0147(9) 0.0156(9) 0.0179(10) 0.0014(8) -0.0017(7) -0.0002(7) C3 0.0138(9) 0.0181(9) 0.0168(9) -0.0014(8) 0.0006(7) 0.0012(7) C4 0.0177(9) 0.0143(9) 0.0164(9) -0.0011(8) 0.0032(7) -0.0010(7) C5 0.0193(9) 0.0152(9) 0.0160(9) 0.0005(8) 0.0013(7) 0.0021(7) C6 0.0156(9) 0.0156(9) 0.0166(9) -0.0035(8) 0.0024(7) 0.0016(7) C7 0.0182(9) 0.0172(9) 0.0202(10) 0.0005(8) 0.0009(7) -0.0046(7) C8 0.0221(10) 0.0174(10) 0.0178(10) 0.0033(8) 0.0008(7) -0.0025(7) C11 0.0153(9) 0.0084(8) 0.0179(9) -0.0020(7) 0.0004(7) -0.0002(6) C12 0.0200(9) 0.0133(9) 0.0171(9) 0.0007(7) 0.0012(7) 0.0013(7) C13 0.0229(10) 0.0153(9) 0.0242(10) 0.0014(8) 0.0076(8) -0.0009(7) C14 0.0144(9) 0.0175(10) 0.0351(12) -0.0028(9) 0.0019(8) -0.0014(7) C15 0.0188(10) 0.0195(10) 0.0272(11) -0.0052(9) -0.0063(8) 0.0011(7) C16 0.0193(9) 0.0144(9) 0.0180(10) -0.0016(8) -0.0001(7) 0.0015(7) C21 0.0163(9) 0.0119(9) 0.0128(9) 0.0048(7) -0.0012(7) 0.0029(7) C22 0.0155(9) 0.0147(9) 0.0162(9) 0.0022(8) -0.0011(7) 0.0011(7) C23 0.0218(10) 0.0150(9) 0.0152(9) -0.0006(8) -0.0033(7) 0.0009(7) C24 0.0239(10) 0.0194(10) 0.0144(9) -0.0010(8) 0.0033(7) 0.0050(7) C25 0.0171(9) 0.0182(10) 0.0207(10) 0.0025(8) 0.0041(7) 0.0012(7) C26 0.0166(9) 0.0152(9) 0.0181(10) 0.0001(8) -0.0018(7) 0.0005(7) C31 0.0105(8) 0.0169(10) 0.0179(9) 0.0006(7) -0.0021(7) 0.0006(7) C32 0.0157(9) 0.0188(10) 0.0176(9) 0.0006(8) -0.0014(7) 0.0012(7) C33 0.0185(9) 0.0204(10) 0.0228(10) -0.0064(8) -0.0050(8) 0.0032(7) C34 0.0172(9) 0.0151(10) 0.0309(11) -0.0014(9) -0.0045(8) 0.0005(7) C35 0.0163(9) 0.0191(10) 0.0270(11) 0.0064(9) 0.0009(8) -0.0001(7) C36 0.0144(9) 0.0187(9) 0.0198(10) -0.0006(8) 0.0004(7) 0.0020(7) C41 0.0131(8) 0.0170(9) 0.0142(9) -0.0022(7) 0.0030(7) 0.0021(7) C42 0.0181(9) 0.0183(10) 0.0191(10) -0.0004(8) 0.0017(7) 0.0012(7) C43 0.0243(10) 0.0214(10) 0.0218(10) 0.0047(8) 0.0051(8) 0.0058(8) C44 0.0234(10) 0.0347(12) 0.0137(10) 0.0049(9) 0.0005(8) 0.0106(8) C45 0.0157(9) 0.0340(11) 0.0157(9) -0.0023(9) -0.0016(7) 0.0025(8) C46 0.0177(9) 0.0189(10) 0.0160(9) -0.0011(8) 0.0018(7) 0.0003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C41 1.632(3) . ? B1 C21 1.640(3) . ? B1 C31 1.648(3) . ? B1 C11 1.649(3) . ? O1 C1 1.223(2) . ? O2 C3 1.229(2) . ? N1 C1 1.335(2) . ? N1 H1B 0.8800 . ? N1 H1A 0.8800 . ? N2 C4 1.344(2) . ? N2 C8 1.349(2) . ? N2 C2 1.470(2) . ? N3 C3 1.330(2) . ? N3 H3B 0.8800 . ? N3 H3A 0.8800 . ? C1 C2 1.523(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C6 1.510(2) . ? C4 C5 1.372(3) . ? C4 H4 0.9500 . ? C5 C6 1.393(2) . ? C5 H5 0.9500 . ? C6 C7 1.388(2) . ? C7 C8 1.372(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C11 C16 1.402(2) . ? C11 C12 1.403(2) . ? C12 C13 1.391(2) . ? C12 H12 0.9500 . ? C13 C14 1.381(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.395(2) . ? C21 C26 1.410(2) . ? C22 C23 1.395(2) . ? C22 H22 0.9500 . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 C25 1.386(3) . ? C24 H24 0.9500 . ? C25 C26 1.385(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.399(3) . ? C31 C32 1.407(2) . ? C32 C33 1.388(2) . ? C32 H32 0.9500 . ? C33 C34 1.389(3) . ? C33 H33 0.9500 . ? C34 C35 1.389(3) . ? C34 H34 0.9500 . ? C35 C36 1.399(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.402(2) . ? C41 C42 1.405(2) . ? C42 C43 1.385(3) . ? C42 H42 0.9500 . ? C43 C44 1.386(3) . ? C43 H43 0.9500 . ? C44 C45 1.386(3) . ? C44 H44 0.9500 . ? C45 C46 1.389(2) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C41 B1 C21 104.50(14) . . ? C41 B1 C31 111.92(14) . . ? C21 B1 C31 111.25(14) . . ? C41 B1 C11 111.62(14) . . ? C21 B1 C11 113.21(14) . . ? C31 B1 C11 104.54(14) . . ? C1 N1 H1B 120.0 . . ? C1 N1 H1A 120.0 . . ? H1B N1 H1A 120.0 . . ? C4 N2 C8 121.31(15) . . ? C4 N2 C2 119.06(14) . . ? C8 N2 C2 119.63(15) . . ? C3 N3 H3B 120.0 . . ? C3 N3 H3A 120.0 . . ? H3B N3 H3A 120.0 . . ? O1 C1 N1 124.66(18) . . ? O1 C1 C2 121.88(16) . . ? N1 C1 C2 113.44(16) . . ? N2 C2 C1 111.72(14) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? O2 C3 N3 124.08(16) . . ? O2 C3 C6 119.18(16) . . ? N3 C3 C6 116.72(16) . . ? N2 C4 C5 120.35(16) . . ? N2 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.68(17) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 118.61(16) . . ? C7 C6 C3 124.23(16) . . ? C5 C6 C3 117.15(16) . . ? C8 C7 C6 119.84(16) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N2 C8 C7 120.19(17) . . ? N2 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C16 C11 C12 115.28(16) . . ? C16 C11 B1 122.53(15) . . ? C12 C11 B1 121.90(15) . . ? C13 C12 C11 122.60(17) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C14 C13 C12 120.42(18) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 118.72(17) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C14 C15 C16 120.36(18) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 122.53(17) . . ? C15 C16 H16 118.7 . . ? C11 C16 H16 118.7 . . ? C22 C21 C26 115.13(15) . . ? C22 C21 B1 124.28(15) . . ? C26 C21 B1 120.48(15) . . ? C23 C22 C21 122.82(16) . . ? C23 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? C24 C23 C22 120.02(17) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 119.19(17) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C26 120.06(17) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 122.75(16) . . ? C25 C26 H26 118.6 . . ? C21 C26 H26 118.6 . . ? C36 C31 C32 115.15(16) . . ? C36 C31 B1 124.28(15) . . ? C32 C31 B1 120.41(15) . . ? C33 C32 C31 122.71(17) . . ? C33 C32 H32 118.6 . . ? C31 C32 H32 118.6 . . ? C32 C33 C34 120.66(17) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C33 C34 C35 118.40(17) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? C34 C35 C36 120.20(17) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C35 C36 C31 122.84(17) . . ? C35 C36 H36 118.6 . . ? C31 C36 H36 118.6 . . ? C46 C41 C42 115.31(16) . . ? C46 C41 B1 124.18(16) . . ? C42 C41 B1 120.27(15) . . ? C43 C42 C41 122.85(17) . . ? C43 C42 H42 118.6 . . ? C41 C42 H42 118.6 . . ? C42 C43 C44 120.00(18) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C43 C44 C45 119.14(17) . . ? C43 C44 H44 120.4 . . ? C45 C44 H44 120.4 . . ? C44 C45 C46 120.07(17) . . ? C44 C45 H45 120.0 . . ? C46 C45 H45 120.0 . . ? C45 C46 C41 122.61(17) . . ? C45 C46 H46 118.7 . . ? C41 C46 H46 118.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.315 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.100 data_br _database_code_depnum_ccdc_archive 'CCDC 879095' #TrackingRef 'Salts 1-4 KMLee.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Br N3 O2' _chemical_formula_weight 260.10 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' 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 'C 1 c 1' _symmetry_space_group_name_hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 5.03600(10) _cell_length_b 28.8208(7) _cell_length_c 6.9016(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.0290(10) _cell_angle_gamma 90.00 _cell_volume 946.97(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3119 _cell_measurement_theta_min 3.4277 _cell_measurement_theta_max 26.3810 _exptl_crystal_description Lamellar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 4.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5061 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 3519 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0700 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 26.38 _reflns_number_total 1625 _reflns_number_gt 1529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.41(2) _refine_ls_number_reflns 1625 _refine_ls_number_parameters 128 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.114 _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 Br1 Br 0.54574(19) 0.888811(17) 0.49717(17) 0.0255(2) Uani 1 1 d . . . C4 C 0.163(3) 0.1161(3) 0.384(2) 0.030(3) Uani 1 1 d . . . H4 H 0.2240 0.0961 0.2977 0.036 Uiso 1 1 calc R . . C5 C 0.2374(16) 0.1625(2) 0.3992(11) 0.0254(16) Uani 1 1 d . . . H5 H 0.3573 0.1742 0.3291 0.030 Uiso 1 1 calc R . . C6 C 0.1343(15) 0.1919(3) 0.5182(11) 0.0251(16) Uani 1 1 d . . . C7 C -0.0261(15) 0.1735(2) 0.6282(12) 0.0230(15) Uani 1 1 d . . . H7 H -0.0930 0.1929 0.7138 0.028 Uiso 1 1 calc R . . C8 C -0.0888(17) 0.1260(4) 0.6118(14) 0.0240(18) Uani 1 1 d . . . H8 H -0.1987 0.1131 0.6871 0.029 Uiso 1 1 calc R . . C2 C -0.0939(15) 0.0503(2) 0.4554(12) 0.0251(15) Uani 1 1 d . . . H2A H -0.2058 0.0467 0.3089 0.030 Uiso 1 1 calc R . . H2B H -0.2184 0.0435 0.5370 0.030 Uiso 1 1 calc R . . C1 C 0.1436(16) 0.0156(2) 0.5097(11) 0.0258(15) Uani 1 1 d . . . C3 C 0.2126(15) 0.2425(2) 0.5223(11) 0.0229(14) Uani 1 1 d . . . N2 N 0.0032(13) 0.0990(2) 0.4928(14) 0.0224(14) Uani 1 1 d . . . N1 N 0.049(2) -0.02838(18) 0.4802(15) 0.0321(14) Uani 1 1 d . . . H1B H 0.1689 -0.0516 0.5064 0.039 Uiso 1 1 calc R . . H1A H -0.1328 -0.0339 0.4349 0.039 Uiso 1 1 calc R . . N3 N 0.0168(13) 0.2719(2) 0.5369(10) 0.0279(17) Uani 1 1 d . . . H3B H 0.0477 0.3020 0.5400 0.033 Uiso 1 1 calc R . . H3A H -0.1438 0.2613 0.5436 0.033 Uiso 1 1 calc R . . O1 O 0.3896(11) 0.02662(18) 0.5716(8) 0.0294(11) Uani 1 1 d . . . O2 O 0.4412(11) 0.25402(17) 0.5123(9) 0.0286(11) 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 Br1 0.0211(3) 0.0292(3) 0.0278(3) -0.0010(4) 0.0102(2) -0.0007(3) C4 0.026(5) 0.036(5) 0.032(6) 0.001(3) 0.014(4) 0.004(3) C5 0.019(4) 0.034(4) 0.025(4) 0.003(3) 0.008(3) 0.002(3) C6 0.015(3) 0.035(3) 0.024(4) 0.000(3) 0.005(3) 0.000(2) C7 0.013(3) 0.031(3) 0.026(4) -0.002(3) 0.007(3) 0.001(3) C8 0.015(4) 0.039(4) 0.023(5) 0.007(4) 0.012(3) 0.005(4) C2 0.022(4) 0.024(3) 0.029(3) 0.004(3) 0.009(3) 0.003(3) C1 0.027(4) 0.031(4) 0.022(3) 0.001(3) 0.012(3) 0.002(3) C3 0.016(3) 0.032(3) 0.023(3) -0.003(3) 0.009(3) 0.000(3) N2 0.014(4) 0.029(2) 0.028(3) 0.005(4) 0.012(3) 0.001(2) N1 0.025(3) 0.028(2) 0.043(4) -0.002(4) 0.010(3) 0.001(4) N3 0.016(3) 0.029(3) 0.041(5) -0.002(3) 0.013(3) -0.001(3) O1 0.019(3) 0.035(3) 0.037(3) -0.001(2) 0.014(2) 0.003(2) O2 0.020(3) 0.035(3) 0.035(3) 0.002(2) 0.015(2) -0.0038(19) _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 C4 N2 1.359(17) . ? C4 C5 1.384(11) . ? C4 H4 0.9500 . ? C5 C6 1.392(11) . ? C5 H5 0.9500 . ? C6 C7 1.381(11) . ? C6 C3 1.510(10) . ? C7 C8 1.403(14) . ? C7 H7 0.9500 . ? C8 N2 1.320(13) . ? C8 H8 0.9500 . ? C2 N2 1.479(9) . ? C2 C1 1.511(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 O1 1.214(9) . ? C1 N1 1.345(9) . ? C3 O2 1.222(9) . ? C3 N3 1.328(9) . ? N1 H1B 0.8800 . ? N1 H1A 0.8800 . ? N3 H3B 0.8800 . ? N3 H3A 0.8800 . ? 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 N2 C4 C5 120.3(11) . . ? N2 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.2(9) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 119.3(7) . . ? C7 C6 C3 123.8(7) . . ? C5 C6 C3 116.9(7) . . ? C6 C7 C8 119.1(7) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? N2 C8 C7 120.7(9) . . ? N2 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? N2 C2 C1 113.3(6) . . ? N2 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N2 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? O1 C1 N1 124.8(7) . . ? O1 C1 C2 123.2(7) . . ? N1 C1 C2 112.0(7) . . ? O2 C3 N3 124.6(7) . . ? O2 C3 C6 120.4(6) . . ? N3 C3 C6 114.9(6) . . ? C8 N2 C4 121.3(6) . . ? C8 N2 C2 120.3(8) . . ? C4 N2 C2 118.0(8) . . ? C1 N1 H1B 120.0 . . ? C1 N1 H1A 120.0 . . ? H1B N1 H1A 120.0 . . ? C3 N3 H3B 120.0 . . ? C3 N3 H3A 120.0 . . ? H3B N3 H3A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.899 _refine_diff_density_min -1.678 _refine_diff_density_rms 0.158