# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Lee, Kwang-Ming' _publ_contact_author_name 'Lee, Kwang-Ming' _publ_contact_author_email kmlee@nknu.edu.tw _publ_section_title ; Anion-Controlled Assemblies of C-H---O Hydrogen Bonded Grid, Stair or Bilayer Structures by L-shaped Pyridinium Salts ; # Attachment '- Four salts.cif' _publ_requested_journal CrystEngComm _publ_contact_author 'Kwang-Ming Lee' _publ_contact_author_address ; Department of Chemistry National Kaohsiung Normal University, 62, Shen-Shung Road, Kaohsiung 824, Taiwan ; _publ_contact_author_fax 886-7-6051083 _publ_contact_author_phone '886-7-7172930 ext 7119' data_PF6_1 _database_code_depnum_ccdc_archive 'CCDC 791678' #TrackingRef '- Four salts.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 F6 N2 O3 P' _chemical_formula_weight 354.19 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 P2(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 6.2214(5) _cell_length_b 8.6255(6) _cell_length_c 26.3909(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.039(4) _cell_angle_gamma 90.00 _cell_volume 1414.21(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5289 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7040 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12089 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2879 _reflns_number_gt 2562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 2008)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _computing_publication_material 'Bruker APEX2' _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^)+(0.0554P)^2^+0.4436P] 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 2879 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 0.8344(2) 0.75136(16) 0.12101(6) 0.0172(3) Uani 1 1 d . . . H1 H 0.9551 0.6870 0.1157 0.021 Uiso 1 1 calc R . . C2 C 0.7448(3) 0.83948(17) 0.08159(6) 0.0199(3) Uani 1 1 d . . . C3 C 0.5684(3) 0.93328(17) 0.09010(6) 0.0213(3) Uani 1 1 d . . . H3 H 0.5055 0.9951 0.0634 0.026 Uiso 1 1 calc R . . C4 C 0.4851(3) 0.93582(17) 0.13784(6) 0.0218(3) Uani 1 1 d . . . H4 H 0.3641 0.9988 0.1441 0.026 Uiso 1 1 calc R . . C5 C 0.5790(2) 0.84655(17) 0.17588(6) 0.0189(3) Uani 1 1 d . . . H5 H 0.5230 0.8480 0.2087 0.023 Uiso 1 1 calc R . . C6 C 0.8330(3) 0.83487(19) 0.02983(6) 0.0249(4) Uani 1 1 d . . . C7 C 1.0872(3) 0.7160(2) -0.02198(6) 0.0357(4) Uani 1 1 d . . . H7A H 0.9849 0.6603 -0.0455 0.043 Uiso 1 1 calc R . . H7B H 1.1185 0.8184 -0.0369 0.043 Uiso 1 1 calc R . . C8 C 1.2866(3) 0.6263(3) -0.01385(7) 0.0372(4) Uani 1 1 d . . . H8A H 1.3905 0.6860 0.0074 0.056 Uiso 1 1 calc R . . H8B H 1.3472 0.6046 -0.0466 0.056 Uiso 1 1 calc R . . H8C H 1.2551 0.5283 0.0031 0.056 Uiso 1 1 calc R . . C9 C 0.8538(2) 0.66677(16) 0.20909(5) 0.0163(3) Uani 1 1 d . . . H9A H 0.9141 0.5697 0.1957 0.020 Uiso 1 1 calc R . . H9B H 0.7453 0.6388 0.2336 0.020 Uiso 1 1 calc R . . C10 C 1.0328(2) 0.76130(16) 0.23576(5) 0.0156(3) Uani 1 1 d . . . F1 F 0.62559(14) 0.40808(10) 0.15078(3) 0.0229(2) Uani 1 1 d . . . F2 F 0.10913(15) 0.40837(11) 0.14802(4) 0.0284(3) Uani 1 1 d . . . F3 F 0.37377(16) 0.26798(11) 0.18961(4) 0.0276(2) Uani 1 1 d . . . F4 F 0.36287(16) 0.54943(11) 0.11030(4) 0.0301(3) Uani 1 1 d . . . F5 F 0.36103(15) 0.28703(11) 0.10393(3) 0.0251(2) Uani 1 1 d . . . F6 F 0.37343(16) 0.52859(12) 0.19580(4) 0.0301(3) Uani 1 1 d . . . N1 N 0.7505(2) 0.75670(13) 0.16702(5) 0.0153(3) Uani 1 1 d . . . N2 N 1.1190(2) 0.69403(14) 0.27707(5) 0.0186(3) Uani 1 1 d . . . H2A H 1.2252 0.7395 0.2947 0.022 Uiso 1 1 calc R . . H2B H 1.0700 0.6038 0.2869 0.022 Uiso 1 1 calc R . . O1 O 0.7613(2) 0.91309(15) -0.00482(4) 0.0366(3) Uani 1 1 d . . . O2 O 0.9944(2) 0.73577(14) 0.02776(4) 0.0293(3) Uani 1 1 d . . . O3 O 1.08915(18) 0.88704(12) 0.21873(4) 0.0218(3) Uani 1 1 d . . . P1 P 0.36636(6) 0.40833(4) 0.149328(14) 0.01490(13) 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 0.0166(7) 0.0181(7) 0.0167(7) -0.0024(5) -0.0001(6) 0.0023(6) C2 0.0214(8) 0.0213(8) 0.0168(7) -0.0012(6) -0.0014(6) 0.0022(6) C3 0.0215(8) 0.0203(7) 0.0216(8) 0.0013(6) -0.0038(6) 0.0029(6) C4 0.0190(8) 0.0190(7) 0.0274(8) -0.0026(6) 0.0013(6) 0.0039(6) C5 0.0194(8) 0.0171(7) 0.0204(7) -0.0039(6) 0.0036(6) -0.0004(6) C6 0.0270(9) 0.0307(9) 0.0168(8) 0.0011(6) -0.0004(6) 0.0081(7) C7 0.0457(11) 0.0468(11) 0.0157(8) 0.0043(7) 0.0119(8) 0.0160(9) C8 0.0302(10) 0.0559(12) 0.0264(9) -0.0025(8) 0.0108(8) 0.0052(9) C9 0.0190(7) 0.0172(7) 0.0126(7) 0.0004(5) -0.0015(6) -0.0013(6) C10 0.0155(7) 0.0161(7) 0.0154(7) -0.0053(5) 0.0032(6) 0.0022(5) F1 0.0150(5) 0.0289(5) 0.0248(5) -0.0022(4) 0.0003(4) -0.0004(4) F2 0.0144(5) 0.0335(6) 0.0375(6) -0.0009(4) 0.0032(4) 0.0027(4) F3 0.0313(5) 0.0265(5) 0.0252(5) 0.0099(4) 0.0036(4) 0.0013(4) F4 0.0329(6) 0.0251(5) 0.0322(6) 0.0124(4) 0.0004(4) 0.0023(4) F5 0.0253(5) 0.0282(5) 0.0216(5) -0.0087(4) 0.0001(4) -0.0019(4) F6 0.0330(6) 0.0305(5) 0.0274(5) -0.0137(4) 0.0059(4) -0.0005(4) N1 0.0172(6) 0.0141(6) 0.0145(6) -0.0016(4) -0.0015(5) 0.0002(5) N2 0.0184(6) 0.0188(6) 0.0181(6) -0.0026(5) -0.0032(5) -0.0011(5) O1 0.0412(8) 0.0497(8) 0.0186(6) 0.0084(5) 0.0007(6) 0.0204(6) O2 0.0355(7) 0.0374(7) 0.0157(6) 0.0044(5) 0.0067(5) 0.0167(5) O3 0.0235(6) 0.0167(5) 0.0249(6) -0.0007(4) -0.0015(5) -0.0032(4) P1 0.0142(2) 0.0157(2) 0.0148(2) 0.00003(13) 0.00079(15) 0.00139(13) _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 1.348(2) . ? C1 C2 1.382(2) . ? C1 H1 0.9500 . ? C2 C3 1.391(2) . ? C2 C6 1.499(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.371(2) . ? C4 H4 0.9500 . ? C5 N1 1.3492(19) . ? C5 H5 0.9500 . ? C6 O1 1.2028(19) . ? C6 O2 1.322(2) . ? C7 C8 1.468(3) . ? C7 O2 1.4718(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N1 1.4735(17) . ? C9 C10 1.522(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O3 1.2319(18) . ? C10 N2 1.3231(19) . ? F1 P1 1.6112(10) . ? F2 P1 1.5989(10) . ? F3 P1 1.6102(9) . ? F4 P1 1.5939(9) . ? F5 P1 1.5897(9) . ? F6 P1 1.6050(9) . ? N2 H2A 0.8800 . ? N2 H2B 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 N1 C1 C2 119.97(13) . . ? N1 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 119.26(14) . . ? C1 C2 C6 121.25(14) . . ? C3 C2 C6 119.49(14) . . ? C4 C3 C2 119.43(14) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 119.40(14) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 120.39(14) . . ? N1 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? O1 C6 O2 125.65(15) . . ? O1 C6 C2 122.61(15) . . ? O2 C6 C2 111.74(13) . . ? C8 C7 O2 107.39(14) . . ? C8 C7 H7A 110.2 . . ? O2 C7 H7A 110.2 . . ? C8 C7 H7B 110.2 . . ? O2 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 110.22(12) . . ? N1 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? N1 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O3 C10 N2 125.18(14) . . ? O3 C10 C9 121.21(13) . . ? N2 C10 C9 113.61(12) . . ? C1 N1 C5 121.56(13) . . ? C1 N1 C9 119.11(12) . . ? C5 N1 C9 119.29(12) . . ? C10 N2 H2A 120.0 . . ? C10 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C6 O2 C7 116.52(13) . . ? F5 P1 F4 90.94(5) . . ? F5 P1 F2 90.17(5) . . ? F4 P1 F2 90.38(5) . . ? F5 P1 F6 179.03(6) . . ? F4 P1 F6 89.96(6) . . ? F2 P1 F6 90.18(5) . . ? F5 P1 F3 90.08(5) . . ? F4 P1 F3 178.68(6) . . ? F2 P1 F3 90.46(5) . . ? F6 P1 F3 89.01(6) . . ? F5 P1 F1 89.88(5) . . ? F4 P1 F1 89.75(5) . . ? F2 P1 F1 179.86(6) . . ? F6 P1 F1 89.76(5) . . ? F3 P1 F1 89.41(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.364 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.071 # END data_BF4_2 _database_code_depnum_ccdc_archive 'CCDC 791679' #TrackingRef '- Four salts.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 B F4 N2 O3' _chemical_formula_weight 296.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9302(4) _cell_length_b 8.3680(6) _cell_length_c 26.0876(17) _cell_angle_alpha 89.168(4) _cell_angle_beta 87.153(4) _cell_angle_gamma 87.763(4) _cell_volume 1291.88(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3943 _cell_measurement_theta_min 2.9075 _cell_measurement_theta_max 25.8994 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.588280 _exptl_absorpt_correction_T_max 0.745373 _exptl_absorpt_process_details 'TWINABS V2008/2 (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 5325 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 0.78 _diffrn_reflns_theta_max 26.52 _reflns_number_total 5325 _reflns_number_gt 4226 _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^)+(0.1161P)^2^+0.5336P] 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 5325 _refine_ls_number_parameters 398 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1730 _refine_ls_goodness_of_fit_ref 1.057 _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 B1 B 0.8523(5) 0.6313(4) 0.34122(11) 0.0246(6) Uani 1 1 d . . . B2 B 0.1201(5) 0.1293(4) 0.15673(12) 0.0293(7) Uani 1 1 d . . . F1 F 0.7189(3) 0.7560(2) 0.36092(8) 0.0451(5) Uani 1 1 d . . . F2 F 1.0795(3) 0.6512(2) 0.35088(6) 0.0361(4) Uani 1 1 d . . . F3 F 0.7850(3) 0.4885(2) 0.36360(9) 0.0489(5) Uani 1 1 d . . . F4 F 0.8338(3) 0.6249(3) 0.28847(7) 0.0533(6) Uani 1 1 d . . . F5 F 0.2727(6) 0.2261(4) 0.13231(13) 0.1017(12) Uani 1 1 d . . . F6 F 0.1339(4) 0.1466(4) 0.20883(8) 0.0661(7) Uani 1 1 d . . . F7 F 0.1679(4) -0.0237(3) 0.14177(11) 0.0634(7) Uani 1 1 d . . . F8 F -0.0941(4) 0.1760(4) 0.14403(9) 0.0806(10) Uani 1 1 d . . . N1 N 0.2464(3) 0.2777(3) 0.33676(8) 0.0214(5) Uani 1 1 d . . . N2 N 0.7306(3) 0.7714(3) 0.16171(8) 0.0225(5) Uani 1 1 d . . . O1 O 0.5915(3) 0.1367(2) 0.28333(7) 0.0247(4) Uani 1 1 d . . . N3 N 0.6193(4) 0.3356(3) 0.22377(9) 0.0263(5) Uani 1 1 d . . . H3A H 0.7274 0.2851 0.2054 0.032 Uiso 1 1 calc R . . H3B H 0.5685 0.4308 0.2139 0.032 Uiso 1 1 calc R . . O3 O 0.3854(3) 0.6450(2) 0.21495(7) 0.0238(4) Uani 1 1 d . . . N4 N 0.3597(4) 0.8370(3) 0.27531(8) 0.0252(5) Uani 1 1 d . . . H4A H 0.2533 0.7894 0.2938 0.030 Uiso 1 1 calc R . . H4B H 0.4102 0.9284 0.2854 0.030 Uiso 1 1 calc R . . C1 C 0.3357(4) 0.2738(4) 0.38305(10) 0.0289(6) Uani 1 1 d . A . H1 H 0.4607 0.3371 0.3893 0.035 Uiso 1 1 calc R . . C2 C 0.2448(5) 0.1772(5) 0.42148(11) 0.0420(9) Uani 1 1 d . . . C3 C 0.0637(5) 0.0847(4) 0.41137(11) 0.0382(8) Uani 1 1 d . A . H3 H -0.0005 0.0182 0.4376 0.046 Uiso 1 1 calc R . . C4 C -0.0231(4) 0.0893(3) 0.36335(10) 0.0270(6) Uani 1 1 d . . . H4 H -0.1461 0.0253 0.3560 0.032 Uiso 1 1 calc R A . C5 C 0.0710(4) 0.1878(3) 0.32640(10) 0.0230(5) Uani 1 1 d . A . H5 H 0.0120 0.1927 0.2932 0.028 Uiso 1 1 calc R . . C6 C 0.3539(4) 0.3730(3) 0.29501(10) 0.0221(5) Uani 1 1 d . . . H6A H 0.4244 0.4666 0.3094 0.027 Uiso 1 1 calc R . . H6B H 0.2387 0.4124 0.2712 0.027 Uiso 1 1 calc R . . C7 C 0.5336(4) 0.2688(3) 0.26604(9) 0.0202(5) Uani 1 1 d . . . C8 C 0.9201(5) 0.5812(4) 0.08615(11) 0.0322(6) Uani 1 1 d . B . H8 H 0.9872 0.5160 0.0596 0.039 Uiso 1 1 calc R . . C9 C 0.7274(5) 0.6746(4) 0.07750(11) 0.0369(7) Uani 1 1 d . . . C10 C 0.6320(5) 0.7692(4) 0.11654(10) 0.0306(6) Uani 1 1 d . B . H10 H 0.4978 0.8320 0.1114 0.037 Uiso 1 1 calc R . . C11 C 0.9168(4) 0.6817(3) 0.17072(10) 0.0251(6) Uani 1 1 d . B . H11 H 0.9823 0.6862 0.2031 0.030 Uiso 1 1 calc R . . C12 C 1.0142(4) 0.5828(3) 0.13323(10) 0.0265(6) Uani 1 1 d . . . H12 H 1.1439 0.5170 0.1399 0.032 Uiso 1 1 calc R B . C13 C 0.6232(4) 0.8690(3) 0.20343(9) 0.0224(5) Uani 1 1 d . . . H13A H 0.5524 0.9677 0.1890 0.027 Uiso 1 1 calc R . . H13B H 0.7383 0.8999 0.2273 0.027 Uiso 1 1 calc R . . C14 C 0.4442(4) 0.7711(3) 0.23213(9) 0.0200(5) Uani 1 1 d . . . O5 O 0.5277(12) 0.2422(8) 0.4770(3) 0.0280(12) Uani 0.507(4) 1 d PD A 1 O6 O 0.2977(10) 0.0469(8) 0.5046(2) 0.0440(12) Uani 0.507(4) 1 d PD A 1 C15 C 0.3661(12) 0.1424(9) 0.4723(3) 0.0291(14) Uani 0.507(4) 1 d PD A 1 C16 C 0.6258(15) 0.2491(11) 0.5278(3) 0.0382(17) Uani 0.507(4) 1 d PD A 1 H16A H 0.5062 0.2724 0.5547 0.046 Uiso 0.507(4) 1 calc PR A 1 H16B H 0.7038 0.1460 0.5362 0.046 Uiso 0.507(4) 1 calc PR A 1 C17 C 0.788(7) 0.378(8) 0.5242(15) 0.073(5) Uani 0.507(4) 1 d PD A 1 H17A H 0.9035 0.3544 0.4970 0.110 Uiso 0.507(4) 1 calc PR A 1 H17B H 0.8593 0.3871 0.5571 0.110 Uiso 0.507(4) 1 calc PR A 1 H17C H 0.7076 0.4797 0.5162 0.110 Uiso 0.507(4) 1 calc PR A 1 O5' O 0.4767(12) 0.2976(8) 0.4796(3) 0.0280(12) Uani 0.493(4) 1 d PD A 2 O6' O 0.2177(10) 0.1306(8) 0.5113(2) 0.0440(12) Uani 0.493(4) 1 d PD A 2 C15' C 0.3052(12) 0.2037(10) 0.4757(3) 0.0291(14) Uani 0.493(4) 1 d PD A 2 C16' C 0.5610(16) 0.3170(11) 0.5306(3) 0.0382(17) Uani 0.493(4) 1 d PD A 2 H16C H 0.5465 0.2166 0.5508 0.046 Uiso 0.493(4) 1 calc PR A 2 H16D H 0.4731 0.4034 0.5490 0.046 Uiso 0.493(4) 1 calc PR A 2 C17' C 0.800(7) 0.358(9) 0.5241(15) 0.073(5) Uani 0.493(4) 1 d PD A 2 H17D H 0.8892 0.2642 0.5114 0.110 Uiso 0.493(4) 1 calc PR A 2 H17E H 0.8539 0.3892 0.5572 0.110 Uiso 0.493(4) 1 calc PR A 2 H17F H 0.8147 0.4463 0.4994 0.110 Uiso 0.493(4) 1 calc PR A 2 O7 O 0.7399(10) 0.6371(7) -0.0122(2) 0.0297(9) Uani 0.500(3) 1 d PD B 1 O8 O 0.4604(8) 0.7963(6) 0.02370(19) 0.0252(8) Uani 0.500(3) 1 d PD B 1 C18 C 0.6485(11) 0.7066(8) 0.0240(3) 0.0226(11) Uani 0.500(3) 1 d PD B 1 C19 C 0.3626(10) 0.8199(9) -0.0269(2) 0.0284(10) Uani 0.500(3) 1 d PD B 1 H19A H 0.3465 0.7162 -0.0438 0.034 Uiso 0.500(3) 1 calc PR B 1 H19B H 0.4585 0.8882 -0.0495 0.034 Uiso 0.500(3) 1 calc PR B 1 C20 C 0.1336(9) 0.9013(7) -0.0152(2) 0.0315(9) Uani 0.500(3) 1 d PD B 1 H20A H 0.0410 0.8312 0.0068 0.047 Uiso 0.500(3) 1 calc PR B 1 H20B H 0.0586 0.9234 -0.0473 0.047 Uiso 0.500(3) 1 calc PR B 1 H20C H 0.1532 1.0020 0.0025 0.047 Uiso 0.500(3) 1 calc PR B 1 O7' O 0.6981(10) 0.5695(7) -0.0077(2) 0.0297(9) Uani 0.500(3) 1 d PD B 2 O8' O 0.4157(8) 0.7285(6) 0.02577(19) 0.0252(8) Uani 0.500(3) 1 d PD B 2 C18' C 0.6108(11) 0.6452(8) 0.0274(3) 0.0226(11) Uani 0.500(3) 1 d PD B 2 C19' C 0.3109(10) 0.7427(8) -0.0243(2) 0.0284(10) Uani 0.500(3) 1 d PD B 2 H19C H 0.1453 0.7332 -0.0194 0.034 Uiso 0.500(3) 1 calc PR B 2 H19D H 0.3704 0.6553 -0.0469 0.034 Uiso 0.500(3) 1 calc PR B 2 C20' C 0.3619(10) 0.9006(8) -0.0487(2) 0.0315(9) Uani 0.500(3) 1 d PD B 2 H20D H 0.3137 0.9865 -0.0249 0.047 Uiso 0.500(3) 1 calc PR B 2 H20E H 0.2808 0.9137 -0.0804 0.047 Uiso 0.500(3) 1 calc PR B 2 H20F H 0.5248 0.9051 -0.0566 0.047 Uiso 0.500(3) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0281(14) 0.0270(15) 0.0186(14) -0.0019(12) 0.0036(11) -0.0033(11) B2 0.0323(15) 0.0326(17) 0.0215(15) 0.0014(13) 0.0090(12) 0.0048(12) F1 0.0458(10) 0.0359(10) 0.0518(12) -0.0098(9) 0.0157(8) -0.0002(8) F2 0.0294(8) 0.0535(11) 0.0255(9) 0.0010(8) 0.0038(6) -0.0115(7) F3 0.0405(10) 0.0360(10) 0.0694(14) 0.0132(10) 0.0065(9) -0.0094(8) F4 0.0449(11) 0.0943(17) 0.0199(9) -0.0068(10) -0.0004(7) 0.0072(10) F5 0.128(3) 0.084(2) 0.090(2) -0.0060(18) 0.0625(19) -0.0448(19) F6 0.0552(13) 0.115(2) 0.0268(10) -0.0083(12) 0.0015(9) 0.0085(13) F7 0.0636(13) 0.0349(11) 0.0911(19) -0.0131(12) 0.0011(12) 0.0055(9) F8 0.0707(15) 0.133(3) 0.0345(12) -0.0246(14) -0.0119(10) 0.0663(16) N1 0.0215(10) 0.0258(11) 0.0162(10) -0.0004(9) 0.0053(8) -0.0022(8) N2 0.0242(10) 0.0281(12) 0.0144(10) 0.0006(9) 0.0062(8) -0.0010(8) O1 0.0264(9) 0.0241(10) 0.0230(10) 0.0003(8) 0.0023(7) -0.0004(7) N3 0.0311(11) 0.0245(12) 0.0219(12) -0.0004(9) 0.0103(9) 0.0018(9) O3 0.0277(9) 0.0244(10) 0.0194(9) -0.0004(8) 0.0021(7) -0.0038(7) N4 0.0301(11) 0.0266(12) 0.0182(11) 0.0003(9) 0.0086(8) -0.0039(9) C1 0.0309(13) 0.0403(17) 0.0162(12) -0.0004(11) 0.0031(10) -0.0147(11) C2 0.0435(16) 0.068(2) 0.0158(14) 0.0075(14) 0.0009(12) -0.0303(16) C3 0.0382(15) 0.057(2) 0.0210(14) 0.0095(14) -0.0005(11) -0.0241(14) C4 0.0239(12) 0.0344(15) 0.0231(14) 0.0002(11) 0.0009(10) -0.0081(10) C5 0.0244(12) 0.0256(13) 0.0187(12) -0.0024(10) 0.0013(9) 0.0012(9) C6 0.0253(12) 0.0236(13) 0.0168(12) 0.0017(10) 0.0044(9) -0.0010(9) C7 0.0199(11) 0.0256(13) 0.0154(11) -0.0029(10) 0.0001(9) -0.0040(9) C8 0.0305(14) 0.0460(18) 0.0188(13) -0.0056(12) 0.0070(10) 0.0072(12) C9 0.0315(14) 0.062(2) 0.0150(13) -0.0043(13) 0.0047(11) 0.0149(13) C10 0.0309(13) 0.0436(17) 0.0160(12) 0.0013(12) 0.0025(10) 0.0105(11) C11 0.0227(12) 0.0346(15) 0.0178(12) 0.0025(11) 0.0013(9) -0.0032(10) C12 0.0237(12) 0.0328(15) 0.0223(13) -0.0001(11) 0.0036(10) 0.0021(10) C13 0.0272(12) 0.0243(13) 0.0151(12) -0.0035(10) 0.0056(9) -0.0018(10) C14 0.0181(11) 0.0239(13) 0.0173(11) 0.0040(10) 0.0015(9) 0.0027(9) O5 0.038(3) 0.033(4) 0.0137(12) 0.002(3) -0.0011(18) -0.012(2) O6 0.049(3) 0.063(4) 0.0212(17) 0.015(2) -0.0021(18) -0.029(2) C15 0.030(3) 0.040(4) 0.0175(18) 0.007(3) -0.001(2) -0.007(2) C16 0.049(5) 0.053(6) 0.0142(18) 0.005(3) -0.009(3) -0.016(3) C17 0.091(4) 0.096(12) 0.039(2) 0.024(4) -0.036(3) -0.055(6) O5' 0.038(3) 0.033(4) 0.0137(12) 0.002(3) -0.0011(18) -0.012(2) O6' 0.049(3) 0.063(4) 0.0212(17) 0.015(2) -0.0021(18) -0.029(2) C15' 0.030(3) 0.040(4) 0.0175(18) 0.007(3) -0.001(2) -0.007(2) C16' 0.049(5) 0.053(6) 0.0142(18) 0.005(3) -0.009(3) -0.016(3) C17' 0.091(4) 0.096(12) 0.039(2) 0.024(4) -0.036(3) -0.055(6) O7 0.029(2) 0.043(3) 0.0164(14) -0.004(2) 0.0085(13) -0.004(2) O8 0.032(2) 0.028(3) 0.0162(12) -0.002(2) -0.0007(12) 0.0018(17) C18 0.027(2) 0.023(4) 0.0180(17) 0.005(3) 0.0047(16) -0.004(2) C19 0.034(3) 0.032(3) 0.0201(18) -0.001(3) -0.0062(17) -0.002(2) C20 0.038(2) 0.036(2) 0.0206(19) 0.0055(17) -0.0022(16) -0.0040(17) O7' 0.029(2) 0.043(3) 0.0164(14) -0.004(2) 0.0085(13) -0.004(2) O8' 0.032(2) 0.028(3) 0.0162(12) -0.002(2) -0.0007(12) 0.0018(17) C18' 0.027(2) 0.023(4) 0.0180(17) 0.005(3) 0.0047(16) -0.004(2) C19' 0.034(3) 0.032(3) 0.0201(18) -0.001(3) -0.0062(17) -0.002(2) C20' 0.038(2) 0.036(2) 0.0206(19) 0.0055(17) -0.0022(16) -0.0040(17) _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 F1 1.375(4) . ? B1 F3 1.386(4) . ? B1 F4 1.388(3) . ? B1 F2 1.400(3) . ? B2 F7 1.359(4) . ? B2 F5 1.366(4) . ? B2 F8 1.370(4) . ? B2 F6 1.376(4) . ? N1 C1 1.342(3) . ? N1 C5 1.348(3) . ? N1 C6 1.475(3) . ? N2 C11 1.339(3) . ? N2 C10 1.342(3) . ? N2 C13 1.474(3) . ? O1 C7 1.230(3) . ? N3 C7 1.318(3) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? O3 C14 1.222(3) . ? N4 C14 1.328(3) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? C1 C2 1.380(4) . ? C1 H1 0.9500 . ? C2 C3 1.386(4) . ? C2 C15' 1.498(9) . ? C2 C15 1.558(8) . ? C3 C4 1.378(4) . ? C3 H3 0.9500 . ? C4 C5 1.371(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.528(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 C12 1.374(4) . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.384(4) . ? C9 C18 1.512(8) . ? C9 C18' 1.537(8) . ? C10 H10 0.9500 . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.526(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? O5 C15 1.307(9) . ? O5 C16 1.475(9) . ? O6 C15 1.219(8) . ? C16 C17 1.47(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O5' C15' 1.318(9) . ? O5' C16' 1.458(9) . ? O6' C15' 1.212(8) . ? C16' C17' 1.47(2) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? O7 C18 1.210(8) . ? O8 C18 1.320(8) . ? O8 C19 1.476(7) . ? C19 C20 1.514(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O7' C18' 1.204(8) . ? O8' C18' 1.330(8) . ? O8' C19' 1.475(7) . ? C19' C20' 1.492(8) . ? C19' H19C 0.9900 . ? C19' H19D 0.9900 . ? C20' H20D 0.9800 . ? C20' H20E 0.9800 . ? C20' H20F 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 F1 B1 F3 109.7(2) . . ? F1 B1 F4 109.9(3) . . ? F3 B1 F4 109.5(3) . . ? F1 B1 F2 110.8(2) . . ? F3 B1 F2 108.8(2) . . ? F4 B1 F2 108.1(2) . . ? F7 B2 F5 108.5(3) . . ? F7 B2 F8 110.1(3) . . ? F5 B2 F8 109.7(3) . . ? F7 B2 F6 112.1(3) . . ? F5 B2 F6 108.4(3) . . ? F8 B2 F6 108.0(2) . . ? C1 N1 C5 121.7(2) . . ? C1 N1 C6 119.2(2) . . ? C5 N1 C6 119.0(2) . . ? C11 N2 C10 122.0(2) . . ? C11 N2 C13 119.2(2) . . ? C10 N2 C13 118.7(2) . . ? C7 N3 H3A 120.0 . . ? C7 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C14 N4 H4A 120.0 . . ? C14 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N1 C1 C2 119.6(2) . . ? N1 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C1 C2 C3 119.3(3) . . ? C1 C2 C15' 118.8(4) . . ? C3 C2 C15' 120.2(4) . . ? C1 C2 C15 122.0(4) . . ? C3 C2 C15 117.6(4) . . ? C15' C2 C15 23.3(3) . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 118.8(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 120.6(2) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N1 C6 C7 109.2(2) . . ? N1 C6 H6A 109.8 . . ? C7 C6 H6A 109.8 . . ? N1 C6 H6B 109.8 . . ? C7 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? O1 C7 N3 125.5(2) . . ? O1 C7 C6 120.3(2) . . ? N3 C7 C6 114.1(2) . . ? C12 C8 C9 119.9(3) . . ? C12 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 C18 117.4(4) . . ? C8 C9 C18 121.7(3) . . ? C10 C9 C18' 123.3(3) . . ? C8 C9 C18' 116.5(4) . . ? C18 C9 C18' 21.6(2) . . ? N2 C10 C9 119.4(3) . . ? N2 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N2 C11 C12 120.5(2) . . ? N2 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C8 C12 C11 118.8(2) . . ? C8 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N2 C13 C14 108.8(2) . . ? N2 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? N2 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? O3 C14 N4 124.9(2) . . ? O3 C14 C13 120.9(2) . . ? N4 C14 C13 114.2(2) . . ? C15 O5 C16 116.9(8) . . ? O6 C15 O5 126.6(8) . . ? O6 C15 C2 122.7(6) . . ? O5 C15 C2 110.3(6) . . ? C17 C16 O5 106.2(15) . . ? C17 C16 H16A 110.5 . . ? O5 C16 H16A 110.5 . . ? C17 C16 H16B 110.5 . . ? O5 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? C15' O5' C16' 117.2(8) . . ? O6' C15' O5' 124.3(8) . . ? O6' C15' C2 121.7(7) . . ? O5' C15' C2 113.6(6) . . ? O5' C16' C17' 107.6(15) . . ? O5' C16' H16C 110.2 . . ? C17' C16' H16C 110.2 . . ? O5' C16' H16D 110.2 . . ? C17' C16' H16D 110.2 . . ? H16C C16' H16D 108.5 . . ? C16' C17' H17D 109.5 . . ? C16' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? C16' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? C18 O8 C19 115.5(5) . . ? O7 C18 O8 126.6(7) . . ? O7 C18 C9 120.1(6) . . ? O8 C18 C9 112.7(5) . . ? O8 C19 C20 104.5(5) . . ? O8 C19 H19A 110.8 . . ? C20 C19 H19A 110.8 . . ? O8 C19 H19B 110.8 . . ? C20 C19 H19B 110.8 . . ? H19A C19 H19B 108.9 . . ? C18' O8' C19' 117.2(5) . . ? O7' C18' O8' 125.0(7) . . ? O7' C18' C9 123.4(6) . . ? O8' C18' C9 111.2(5) . . ? O8' C19' C20' 109.7(5) . . ? O8' C19' H19C 109.7 . . ? C20' C19' H19C 109.7 . . ? O8' C19' H19D 109.7 . . ? C20' C19' H19D 109.7 . . ? H19C C19' H19D 108.2 . . ? C19' C20' H20D 109.5 . . ? C19' C20' H20E 109.5 . . ? H20D C20' H20E 109.5 . . ? C19' C20' H20F 109.5 . . ? H20D C20' H20F 109.5 . . ? H20E C20' H20F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.52 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.866 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.139 # END data_OTF_3 _database_code_depnum_ccdc_archive 'CCDC 791680' #TrackingRef '- Four salts.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 F6 N4 O12 S2' _chemical_formula_weight 716.59 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.812(2) _cell_length_b 11.241(2) _cell_length_c 13.008(2) _cell_angle_alpha 88.651(4) _cell_angle_beta 86.423(4) _cell_angle_gamma 73.822(4) _cell_volume 1515.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9947 _cell_measurement_theta_min 2.8670 _cell_measurement_theta_max 26.3498 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5630 _exptl_absorpt_correction_T_max 0.7454 _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 29345 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.44 _reflns_number_total 5996 _reflns_number_gt 5184 _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^)+(0.0881P)^2^+4.7587P] 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 5996 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1991 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 0.6163(3) 0.8047(3) 0.0952(3) 0.0211(7) Uani 1 1 d . . . H1 H 0.5555 0.8794 0.0758 0.025 Uiso 1 1 calc R . . C2 C 0.5861(3) 0.7369(3) 0.1779(3) 0.0214(7) Uani 1 1 d . . . H2 H 0.5054 0.7650 0.2156 0.026 Uiso 1 1 calc R . . C3 C 0.6739(3) 0.6281(3) 0.2056(3) 0.0186(7) Uani 1 1 d . . . H3 H 0.6551 0.5810 0.2630 0.022 Uiso 1 1 calc R . . C4 C 0.7909(3) 0.5886(3) 0.1480(2) 0.0175(7) Uani 1 1 d . . . C5 C 0.8180(3) 0.6596(3) 0.0661(3) 0.0191(7) Uani 1 1 d . . . H5 H 0.8980 0.6336 0.0271 0.023 Uiso 1 1 calc R . . C6 C 0.7616(3) 0.8417(3) -0.0453(3) 0.0208(7) Uani 1 1 d . . . H6A H 0.6825 0.9051 -0.0643 0.025 Uiso 1 1 calc R . . H6B H 0.7949 0.7877 -0.1057 0.025 Uiso 1 1 calc R . . C7 C 0.8630(3) 0.9055(3) -0.0174(3) 0.0201(7) Uani 1 1 d . . . C8 C 0.8904(3) 0.4705(3) 0.1712(3) 0.0201(7) Uani 1 1 d . . . C9 C 0.9548(4) 0.3083(4) 0.2917(3) 0.0272(8) Uani 1 1 d . . . H9A H 1.0407 0.3205 0.3003 0.033 Uiso 1 1 calc R . . H9B H 0.9637 0.2442 0.2386 0.033 Uiso 1 1 calc R . . C10 C 0.9005(5) 0.2697(5) 0.3918(4) 0.0419(11) Uani 1 1 d . . . H10A H 0.8840 0.3374 0.4413 0.063 Uiso 1 1 calc R . . H10B H 0.9625 0.1964 0.4188 0.063 Uiso 1 1 calc R . . H10C H 0.8196 0.2501 0.3805 0.063 Uiso 1 1 calc R . . C11 C 0.6884(3) 0.8634(3) 0.4082(3) 0.0238(8) Uani 1 1 d . . . H11 H 0.6072 0.9189 0.4283 0.029 Uiso 1 1 calc R . . C12 C 0.7576(4) 0.8906(4) 0.3228(3) 0.0250(8) Uani 1 1 d . . . H12 H 0.7251 0.9648 0.2848 0.030 Uiso 1 1 calc R . . C13 C 0.8753(3) 0.8083(3) 0.2929(3) 0.0208(7) Uani 1 1 d . . . H13 H 0.9240 0.8247 0.2336 0.025 Uiso 1 1 calc R . . C14 C 0.9209(3) 0.7010(3) 0.3512(3) 0.0198(7) Uani 1 1 d . . . C15 C 0.8481(3) 0.6781(3) 0.4367(3) 0.0203(7) Uani 1 1 d . . . H15 H 0.8785 0.6049 0.4764 0.024 Uiso 1 1 calc R . . C16 C 0.6543(3) 0.7308(4) 0.5518(3) 0.0233(7) Uani 1 1 d . . . H16A H 0.5907 0.8078 0.5765 0.028 Uiso 1 1 calc R . . H16B H 0.7101 0.6959 0.6089 0.028 Uiso 1 1 calc R . . C17 C 0.5837(3) 0.6379(3) 0.5213(3) 0.0217(7) Uani 1 1 d . . . C18 C 1.0456(3) 0.6060(3) 0.3236(3) 0.0224(7) Uani 1 1 d . . . C19 C 1.2155(4) 0.5427(4) 0.1936(3) 0.0319(9) Uani 1 1 d . . . H19A H 1.2213 0.5423 0.1173 0.038 Uiso 1 1 calc R . . H19B H 1.2202 0.4575 0.2180 0.038 Uiso 1 1 calc R . . C20 C 1.3257(4) 0.5818(4) 0.2318(4) 0.0367(10) Uani 1 1 d . . . H20A H 1.3154 0.6692 0.2145 0.055 Uiso 1 1 calc R . . H20B H 1.4069 0.5311 0.1993 0.055 Uiso 1 1 calc R . . H20C H 1.3269 0.5707 0.3067 0.055 Uiso 1 1 calc R . . C21 C 0.1862(5) 0.9224(4) 0.3953(3) 0.0367(10) Uani 1 1 d . . . C22 C 0.6697(5) 0.2639(4) 0.0900(3) 0.0377(10) Uani 1 1 d . . . F1 F 0.1467(3) 0.9759(3) 0.48691(19) 0.0465(7) Uani 1 1 d . . . F2 F 0.0795(3) 0.9330(4) 0.3435(3) 0.0668(11) Uani 1 1 d . . . F3 F 0.2407(4) 0.8036(3) 0.4100(2) 0.0695(11) Uani 1 1 d . . . F4 F 0.7893(3) 0.1973(3) 0.1036(3) 0.0576(9) Uani 1 1 d . . . F5 F 0.6548(3) 0.3770(3) 0.1291(3) 0.0621(9) Uani 1 1 d . . . F6 F 0.6565(4) 0.2770(4) -0.0111(2) 0.0678(10) Uani 1 1 d . . . N1 N 0.7299(3) 0.7667(3) 0.0417(2) 0.0188(6) Uani 1 1 d . . . N2 N 0.8737(3) 0.9956(3) -0.0815(2) 0.0255(7) Uani 1 1 d . . . H2A H 0.9321 1.0350 -0.0728 0.031 Uiso 1 1 calc R . . H2B H 0.8225 1.0162 -0.1329 0.031 Uiso 1 1 calc R . . N3 N 0.7340(3) 0.7598(3) 0.4636(2) 0.0207(6) Uani 1 1 d . . . N4 N 0.4825(3) 0.6363(3) 0.5827(2) 0.0262(7) Uani 1 1 d . . . H4A H 0.4386 0.5831 0.5720 0.031 Uiso 1 1 calc R . . H4B H 0.4589 0.6885 0.6343 0.031 Uiso 1 1 calc R . . O1 O 0.9302(3) 0.8698(3) 0.05683(19) 0.0267(6) Uani 1 1 d . . . O2 O 0.9840(3) 0.4254(3) 0.1153(2) 0.0327(7) Uani 1 1 d . . . O3 O 0.8636(3) 0.4247(2) 0.26143(19) 0.0257(6) Uani 1 1 d . . . O4 O 0.6256(3) 0.5691(3) 0.4466(2) 0.0282(6) Uani 1 1 d . . . O5 O 1.0948(3) 0.5211(3) 0.3798(2) 0.0284(6) Uani 1 1 d . . . O6 O 1.0919(3) 0.6277(3) 0.23078(19) 0.0277(6) Uani 1 1 d . . . O7 O 0.3228(2) 0.9304(3) 0.22838(19) 0.0246(6) Uani 1 1 d . . . O8 O 0.4004(3) 0.9763(3) 0.3904(2) 0.0331(7) Uani 1 1 d . . . O9 O 0.2177(3) 1.1236(3) 0.3166(2) 0.0294(6) Uani 1 1 d . . . O10 O 0.5883(3) 0.1775(3) 0.2568(2) 0.0343(7) Uani 1 1 d . . . O11 O 0.4304(3) 0.2829(3) 0.1365(3) 0.0385(7) Uani 1 1 d . . . O12 O 0.5740(3) 0.0794(3) 0.0954(2) 0.0304(6) Uani 1 1 d . . . S1 S 0.29408(8) 0.99745(8) 0.32486(6) 0.0194(2) Uani 1 1 d . . . S2 S 0.55096(9) 0.19356(8) 0.15148(7) 0.0215(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 0.0203(16) 0.0187(17) 0.0259(17) -0.0047(13) -0.0100(13) -0.0059(14) C2 0.0182(16) 0.0217(17) 0.0245(17) -0.0063(14) -0.0022(13) -0.0051(14) C3 0.0218(16) 0.0194(16) 0.0163(15) -0.0036(12) -0.0044(12) -0.0080(14) C4 0.0180(15) 0.0178(16) 0.0175(15) -0.0053(12) -0.0062(12) -0.0048(13) C5 0.0196(16) 0.0213(17) 0.0181(15) -0.0046(13) -0.0042(12) -0.0075(14) C6 0.0248(17) 0.0232(17) 0.0186(16) 0.0009(13) -0.0095(13) -0.0119(15) C7 0.0229(17) 0.0237(17) 0.0167(15) -0.0019(13) -0.0067(13) -0.0099(14) C8 0.0205(16) 0.0204(17) 0.0200(16) -0.0013(13) -0.0049(13) -0.0056(14) C9 0.0273(18) 0.0223(18) 0.0283(19) 0.0047(15) -0.0049(15) -0.0006(15) C10 0.040(2) 0.040(3) 0.038(2) 0.014(2) 0.0027(19) 0.001(2) C11 0.0194(16) 0.0229(18) 0.0301(18) -0.0100(15) -0.0099(14) -0.0046(14) C12 0.0291(19) 0.0225(18) 0.0253(18) -0.0023(14) -0.0152(15) -0.0073(15) C13 0.0255(17) 0.0235(18) 0.0176(15) -0.0025(13) -0.0086(13) -0.0121(15) C14 0.0209(16) 0.0217(17) 0.0195(16) -0.0034(13) -0.0074(13) -0.0085(14) C15 0.0214(16) 0.0215(17) 0.0205(16) -0.0037(13) -0.0069(13) -0.0087(14) C16 0.0208(17) 0.0268(19) 0.0253(17) -0.0110(14) -0.0001(14) -0.0108(15) C17 0.0231(17) 0.0231(18) 0.0209(16) -0.0056(13) -0.0051(13) -0.0085(14) C18 0.0220(17) 0.0231(18) 0.0235(17) -0.0023(14) -0.0023(13) -0.0084(15) C19 0.030(2) 0.036(2) 0.0294(19) -0.0085(16) 0.0054(16) -0.0095(18) C20 0.029(2) 0.038(2) 0.043(2) -0.0061(19) 0.0005(18) -0.0084(18) C21 0.053(3) 0.038(2) 0.0255(19) -0.0152(17) 0.0077(18) -0.025(2) C22 0.048(3) 0.035(2) 0.038(2) -0.0108(18) 0.0003(19) -0.024(2) F1 0.0616(18) 0.0574(18) 0.0281(13) -0.0173(12) 0.0135(12) -0.0313(15) F2 0.0559(19) 0.113(3) 0.0569(19) -0.0330(19) 0.0088(15) -0.065(2) F3 0.133(3) 0.0355(16) 0.0451(17) -0.0056(13) 0.0229(19) -0.038(2) F4 0.0319(14) 0.078(2) 0.068(2) -0.0321(17) 0.0072(13) -0.0224(15) F5 0.068(2) 0.0436(17) 0.090(2) -0.0207(16) 0.0025(18) -0.0392(17) F6 0.101(3) 0.081(2) 0.0379(16) 0.0117(16) 0.0025(16) -0.054(2) N1 0.0219(14) 0.0196(14) 0.0183(13) -0.0031(11) -0.0083(11) -0.0097(12) N2 0.0311(16) 0.0325(17) 0.0208(14) 0.0042(13) -0.0141(12) -0.0197(14) N3 0.0209(14) 0.0230(15) 0.0215(14) -0.0088(12) -0.0055(11) -0.0097(12) N4 0.0306(16) 0.0318(17) 0.0223(15) -0.0138(13) 0.0029(12) -0.0185(14) O1 0.0321(14) 0.0355(15) 0.0199(12) 0.0063(11) -0.0140(10) -0.0196(12) O2 0.0311(15) 0.0292(15) 0.0293(14) 0.0033(11) 0.0057(12) 0.0039(12) O3 0.0264(13) 0.0238(13) 0.0216(12) 0.0026(10) -0.0007(10) 0.0010(11) O4 0.0354(15) 0.0323(15) 0.0228(13) -0.0142(11) 0.0039(11) -0.0191(12) O5 0.0271(14) 0.0261(14) 0.0283(14) 0.0031(11) -0.0008(11) -0.0015(11) O6 0.0276(14) 0.0330(15) 0.0206(12) -0.0010(11) 0.0013(10) -0.0059(12) O7 0.0236(12) 0.0289(14) 0.0192(12) -0.0079(10) -0.0069(10) -0.0021(11) O8 0.0250(14) 0.0402(17) 0.0320(14) -0.0117(12) -0.0187(11) -0.0014(12) O9 0.0267(13) 0.0240(14) 0.0359(15) -0.0063(11) -0.0116(11) -0.0021(11) O10 0.0486(18) 0.0326(15) 0.0193(13) -0.0069(11) -0.0087(12) -0.0054(14) O11 0.0321(15) 0.0313(16) 0.0546(19) -0.0095(14) -0.0164(14) -0.0094(13) O12 0.0428(16) 0.0241(14) 0.0282(14) -0.0094(11) -0.0049(12) -0.0147(13) S1 0.0173(4) 0.0215(4) 0.0197(4) -0.0051(3) -0.0076(3) -0.0042(3) S2 0.0262(5) 0.0199(4) 0.0210(4) -0.0054(3) -0.0068(3) -0.0090(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 1.338(5) . ? C1 C2 1.379(5) . ? C1 H1 0.9500 . ? C2 C3 1.379(5) . ? C2 H2 0.9500 . ? C3 C4 1.394(5) . ? C3 H3 0.9500 . ? C4 C5 1.381(5) . ? C4 C8 1.495(5) . ? C5 N1 1.356(5) . ? C5 H5 0.9500 . ? C6 N1 1.475(4) . ? C6 C7 1.532(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O1 1.236(4) . ? C7 N2 1.323(5) . ? C8 O2 1.204(4) . ? C8 O3 1.320(4) . ? C9 O3 1.464(4) . ? C9 C10 1.499(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N3 1.343(5) . ? C11 C12 1.376(6) . ? C11 H11 0.9500 . ? C12 C13 1.388(5) . ? C12 H12 0.9500 . ? C13 C14 1.395(5) . ? C13 H13 0.9500 . ? C14 C15 1.382(5) . ? C14 C18 1.498(5) . ? C15 N3 1.349(5) . ? C15 H15 0.9500 . ? C16 N3 1.476(5) . ? C16 C17 1.527(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O4 1.238(4) . ? C17 N4 1.317(5) . ? C18 O5 1.208(5) . ? C18 O6 1.322(4) . ? C19 O6 1.471(5) . ? C19 C20 1.495(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 F3 1.316(6) . ? C21 F1 1.339(4) . ? C21 F2 1.347(6) . ? C21 S1 1.814(5) . ? C22 F4 1.321(6) . ? C22 F6 1.333(5) . ? C22 F5 1.344(5) . ? C22 S2 1.822(5) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? O7 S1 1.451(2) . ? O8 S1 1.437(3) . ? O9 S1 1.434(3) . ? O10 S2 1.446(3) . ? O11 S2 1.428(3) . ? O12 S2 1.443(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 120.9(3) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 119.6(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 C8 117.8(3) . . ? C3 C4 C8 122.4(3) . . ? N1 C5 C4 119.7(3) . . ? N1 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? N1 C6 C7 111.1(3) . . ? N1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O1 C7 N2 124.9(3) . . ? O1 C7 C6 121.0(3) . . ? N2 C7 C6 114.0(3) . . ? O2 C8 O3 124.8(3) . . ? O2 C8 C4 124.0(3) . . ? O3 C8 C4 111.2(3) . . ? O3 C9 C10 106.3(3) . . ? O3 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? O3 C9 H9B 110.5 . . ? C10 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 121.1(3) . . ? N3 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 C18 117.7(3) . . ? C13 C14 C18 122.6(3) . . ? N3 C15 C14 120.0(3) . . ? N3 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N3 C16 C17 110.9(3) . . ? N3 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? O4 C17 N4 125.6(3) . . ? O4 C17 C16 120.0(3) . . ? N4 C17 C16 114.3(3) . . ? O5 C18 O6 125.7(3) . . ? O5 C18 C14 123.4(3) . . ? O6 C18 C14 110.9(3) . . ? O6 C19 C20 110.4(3) . . ? O6 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? O6 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? F3 C21 F1 108.7(4) . . ? F3 C21 F2 107.6(4) . . ? F1 C21 F2 106.7(4) . . ? F3 C21 S1 112.1(3) . . ? F1 C21 S1 110.9(3) . . ? F2 C21 S1 110.6(3) . . ? F4 C22 F6 107.5(4) . . ? F4 C22 F5 107.8(4) . . ? F6 C22 F5 107.7(4) . . ? F4 C22 S2 112.2(3) . . ? F6 C22 S2 111.2(3) . . ? F5 C22 S2 110.2(3) . . ? C1 N1 C5 121.1(3) . . ? C1 N1 C6 120.2(3) . . ? C5 N1 C6 118.7(3) . . ? C7 N2 H2A 120.0 . . ? C7 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C11 N3 C15 121.1(3) . . ? C11 N3 C16 119.5(3) . . ? C15 N3 C16 119.2(3) . . ? C17 N4 H4A 120.0 . . ? C17 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C8 O3 C9 115.7(3) . . ? C18 O6 C19 117.1(3) . . ? O9 S1 O8 115.63(17) . . ? O9 S1 O7 114.78(16) . . ? O8 S1 O7 114.88(16) . . ? O9 S1 C21 103.5(2) . . ? O8 S1 C21 102.7(2) . . ? O7 S1 C21 102.85(17) . . ? O11 S2 O12 115.60(18) . . ? O11 S2 O10 115.19(19) . . ? O12 S2 O10 114.33(17) . . ? O11 S2 C22 103.9(2) . . ? O12 S2 C22 102.65(19) . . ? O10 S2 C22 102.6(2) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 1.171 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.105 # END data_Br_4 _database_code_depnum_ccdc_archive 'CCDC 791681' #TrackingRef '- Four salts.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 Br N2 O3.50' _chemical_formula_weight 298.14 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 2/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' '-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 30.056(6) _cell_length_b 5.1055(9) _cell_length_c 20.239(4) _cell_angle_alpha 90.00 _cell_angle_beta 129.083(3) _cell_angle_gamma 90.00 _cell_volume 2410.7(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7702 _cell_measurement_theta_min 2.5930 _cell_measurement_theta_max 26.7058 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 3.410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8374 _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 17929 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.75 _reflns_number_total 2579 _reflns_number_gt 2227 _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^)+(0.0379P)^2^+14.7306P] 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 2579 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Br1 Br 0.046660(13) 0.44717(6) 0.424085(19) 0.02022(11) Uani 1 1 d . . . C1 C 0.13861(12) 0.7705(6) 0.65515(19) 0.0188(6) Uani 1 1 d . . . C2 C 0.10568(13) 0.9641(7) 0.5950(2) 0.0210(6) Uani 1 1 d . . . H2 H 0.1104 1.0050 0.5540 0.025 Uiso 1 1 calc R . . C3 C 0.06541(13) 1.0984(6) 0.5954(2) 0.0212(6) Uani 1 1 d . . . H3 H 0.0418 1.2289 0.5539 0.025 Uiso 1 1 calc R . . C4 C 0.06033(13) 1.0397(6) 0.6566(2) 0.0192(6) Uani 1 1 d . . . H4 H 0.0332 1.1312 0.6575 0.023 Uiso 1 1 calc R . . C5 C 0.13184(12) 0.7165(6) 0.71531(19) 0.0173(6) Uani 1 1 d . . . H5 H 0.1542 0.5834 0.7565 0.021 Uiso 1 1 calc R . . C6 C 0.08994(13) 0.8156(6) 0.78412(19) 0.0189(6) Uani 1 1 d . . . H6A H 0.1099 0.6519 0.8154 0.023 Uiso 1 1 calc R . . H6B H 0.0493 0.8003 0.7596 0.023 Uiso 1 1 calc R . . C7 C 0.11776(13) 1.0492(6) 0.8453(2) 0.0198(6) Uani 1 1 d . . . C8 C 0.18394(13) 0.6201(7) 0.6614(2) 0.0245(7) Uani 1 1 d . . . C9 C 0.24211(17) 0.6228(11) 0.6190(3) 0.0492(12) Uani 1 1 d . . . H9A H 0.2561 0.7602 0.6016 0.059 Uiso 1 1 calc R . . H9B H 0.2735 0.5803 0.6795 0.059 Uiso 1 1 calc R . . C10 C 0.2277(2) 0.3954(13) 0.5687(4) 0.0704(18) Uani 1 1 d . . . H10A H 0.2155 0.2562 0.5875 0.106 Uiso 1 1 calc R . . H10B H 0.2613 0.3367 0.5750 0.106 Uiso 1 1 calc R . . H10C H 0.1964 0.4364 0.5088 0.106 Uiso 1 1 calc R . . N1 N 0.09348(10) 0.8531(5) 0.71546(16) 0.0162(5) Uani 1 1 d . . . N2 N 0.11885(14) 1.0284(6) 0.91215(19) 0.0287(7) Uani 1 1 d . . . H2A H 0.1347 1.1527 0.9509 0.034 Uiso 1 1 calc R . . H2B H 0.1037 0.8904 0.9174 0.034 Uiso 1 1 calc R . . O1 O 0.13769(10) 1.2339(4) 0.83263(15) 0.0227(5) Uani 1 1 d . . . O2 O 0.19326(10) 0.7228(6) 0.61022(15) 0.0345(6) Uani 1 1 d . . . O3 O 0.20838(11) 0.4349(5) 0.70783(17) 0.0322(6) Uani 1 1 d . . . O4 O 0.0000 0.7661(7) 0.2500 0.0320(8) Uani 1 2 d S . . H4A H 0.0178 0.6421 0.3022 0.080 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 0.02363(17) 0.01993(17) 0.02086(17) 0.00298(12) 0.01583(14) 0.00233(12) C1 0.0149(14) 0.0236(16) 0.0183(14) -0.0037(12) 0.0107(12) -0.0021(12) C2 0.0212(15) 0.0259(16) 0.0177(14) -0.0011(13) 0.0132(13) -0.0039(13) C3 0.0201(15) 0.0228(16) 0.0181(14) 0.0033(12) 0.0109(13) 0.0009(12) C4 0.0169(14) 0.0172(14) 0.0219(15) -0.0002(12) 0.0114(13) 0.0008(12) C5 0.0154(14) 0.0181(15) 0.0182(14) -0.0013(11) 0.0105(12) -0.0005(11) C6 0.0228(15) 0.0190(15) 0.0240(15) 0.0027(12) 0.0191(14) 0.0011(12) C7 0.0231(15) 0.0172(14) 0.0257(16) 0.0027(13) 0.0186(14) 0.0038(13) C8 0.0186(15) 0.0350(19) 0.0199(15) -0.0047(14) 0.0122(13) 0.0014(14) C9 0.0269(19) 0.094(4) 0.035(2) 0.007(2) 0.0237(18) 0.018(2) C10 0.034(2) 0.098(5) 0.067(3) -0.039(3) 0.026(2) 0.003(3) N1 0.0165(12) 0.0153(12) 0.0195(12) 0.0005(10) 0.0126(11) -0.0013(10) N2 0.0455(18) 0.0223(14) 0.0321(16) -0.0043(12) 0.0311(15) -0.0071(13) O1 0.0300(12) 0.0168(11) 0.0316(12) 0.0008(9) 0.0243(11) -0.0005(9) O2 0.0194(11) 0.068(2) 0.0218(12) 0.0040(12) 0.0158(10) 0.0092(12) O3 0.0283(13) 0.0347(15) 0.0368(14) -0.0005(12) 0.0220(12) 0.0086(11) O4 0.0325(19) 0.033(2) 0.0328(19) 0.000 0.0216(17) 0.000 _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 C5 1.383(4) . ? C1 C2 1.385(5) . ? C1 C8 1.498(4) . ? C2 C3 1.395(5) . ? C2 H2 0.9500 . ? C3 C4 1.372(4) . ? C3 H3 0.9500 . ? C4 N1 1.350(4) . ? C4 H4 0.9500 . ? C5 N1 1.349(4) . ? C5 H5 0.9500 . ? C6 N1 1.472(4) . ? C6 C7 1.533(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O1 1.228(4) . ? C7 N2 1.336(4) . ? C8 O3 1.203(4) . ? C8 O2 1.338(4) . ? C9 C10 1.420(7) . ? C9 O2 1.456(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? O4 H4A 1.0442 . ? 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 C1 C2 119.7(3) . . ? C5 C1 C8 117.0(3) . . ? C2 C1 C8 123.2(3) . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 119.2(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? N1 C4 C3 120.7(3) . . ? N1 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? N1 C5 C1 120.0(3) . . ? N1 C5 H5 120.0 . . ? C1 C5 H5 120.0 . . ? N1 C6 C7 109.5(2) . . ? N1 C6 H6A 109.8 . . ? C7 C6 H6A 109.8 . . ? N1 C6 H6B 109.8 . . ? C7 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? O1 C7 N2 124.7(3) . . ? O1 C7 C6 121.2(3) . . ? N2 C7 C6 114.1(3) . . ? O3 C8 O2 126.1(3) . . ? O3 C8 C1 122.9(3) . . ? O2 C8 C1 110.9(3) . . ? C10 C9 O2 111.8(4) . . ? C10 C9 H9A 109.3 . . ? O2 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? O2 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 N1 C4 121.2(3) . . ? C5 N1 C6 120.4(3) . . ? C4 N1 C6 118.2(2) . . ? C7 N2 H2A 120.0 . . ? C7 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C8 O2 C9 117.1(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.911 _refine_diff_density_min -0.862 _refine_diff_density_rms 0.098