# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_MV(BF4) _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2, B F4' _chemical_formula_sum 'C12 H14 B F4 N2' _chemical_formula_weight 273.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source B B 0.0013 0.0007 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 6.5851(5) _cell_length_b 16.5308(10) _cell_length_c 11.7122(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.640(10) _cell_angle_gamma 90.00 _cell_volume 1272.38(16) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 14674 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 26.52 _reflns_number_total 2615 _reflns_number_gt 1484 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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. The BF4- anion in the structure is disordered over two positions of different occupancies refined to 0.689(8) and 0.311(8). SIMU restraints were applied to refine the corresponding disordered F atoms anisotropically. ; _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^)+(0.0422P)^2^+1.0317P] 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 2615 _refine_ls_number_parameters 211 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.055 _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 0.5591(4) -0.01679(19) 0.7606(3) 0.0487(8) Uani 1 1 d . . . H1 H 0.5729 -0.0549 0.8190 0.058 Uiso 1 1 calc R . . C2 C 0.5343(4) -0.04237(17) 0.6508(2) 0.0405(7) Uani 1 1 d . . . H2 H 0.5317 -0.0976 0.6358 0.049 Uiso 1 1 calc R . . C3 C 0.5120(4) 0.01275(15) 0.5581(2) 0.0323(6) Uani 1 1 d . . . C4 C 0.5196(4) 0.09601(16) 0.5905(2) 0.0361(6) Uani 1 1 d . . . H4 H 0.5068 0.1357 0.5342 0.043 Uiso 1 1 calc R . . C5 C 0.5450(4) 0.11791(18) 0.7009(3) 0.0440(7) Uani 1 1 d . . . H5 H 0.5496 0.1727 0.7189 0.053 Uiso 1 1 calc R . . C6 C 0.5947(6) 0.0894(3) 0.9068(3) 0.0792(12) Uani 1 1 d . . . H6A H 0.6562 0.1420 0.9097 0.119 Uiso 1 1 calc R . . H6B H 0.6821 0.0517 0.9485 0.119 Uiso 1 1 calc R . . H6C H 0.4657 0.0916 0.9406 0.119 Uiso 1 1 calc R . . C7 C 1.0500(4) 0.08818(17) 0.7306(2) 0.0395(7) Uani 1 1 d . . . H7 H 1.0641 0.0795 0.8091 0.047 Uiso 1 1 calc R . . C8 C 1.0327(4) 0.02349(16) 0.6597(2) 0.0346(6) Uani 1 1 d . . . H8 H 1.0357 -0.0284 0.6906 0.042 Uiso 1 1 calc R . . C9 C 1.0101(4) 0.03345(15) 0.5385(2) 0.0331(6) Uani 1 1 d . . . C10 C 1.0089(4) 0.11533(16) 0.5007(2) 0.0390(7) Uani 1 1 d . . . H10 H 0.9963 0.1265 0.4227 0.047 Uiso 1 1 calc R . . C11 C 1.0257(4) 0.17725(17) 0.5765(2) 0.0430(7) Uani 1 1 d . . . H11 H 1.0222 0.2300 0.5488 0.052 Uiso 1 1 calc R . . C12 C 1.0687(5) 0.23438(19) 0.7692(3) 0.0607(9) Uani 1 1 d . . . H12A H 1.0874 0.2150 0.8464 0.091 Uiso 1 1 calc R . . H12B H 0.9482 0.2671 0.7614 0.091 Uiso 1 1 calc R . . H12C H 1.1844 0.2661 0.7511 0.091 Uiso 1 1 calc R . . N1 N 0.5643(3) 0.06310(16) 0.7875(2) 0.0472(6) Uani 1 1 d . . . N2 N 1.0472(3) 0.16536(14) 0.6907(2) 0.0413(6) Uani 1 1 d . . . B B 0.9642(6) -0.1553(2) 0.8924(3) 0.0464(8) Uani 1 1 d . . . F1A F 1.0950(16) -0.2090(8) 0.9493(12) 0.075(2) Uani 0.689(8) 1 d PU A 1 F2A F 0.9310(14) -0.1766(6) 0.7763(6) 0.0747(19) Uani 0.689(8) 1 d PU A 1 F3A F 0.7746(7) -0.1585(4) 0.9390(4) 0.1012(18) Uani 0.689(8) 1 d PU A 1 F4A F 1.0266(11) -0.0769(2) 0.8993(5) 0.098(2) Uani 0.689(8) 1 d PU A 1 F1B F 1.046(4) -0.2139(17) 0.957(3) 0.080(5) Uani 0.311(8) 1 d PU A 2 F2B F 0.873(3) -0.1831(15) 0.8003(15) 0.094(5) Uani 0.311(8) 1 d PU A 2 F3B F 0.865(2) -0.1083(8) 0.9585(8) 0.093(3) Uani 0.311(8) 1 d PU A 2 F4B F 1.136(2) -0.1106(9) 0.8632(9) 0.103(4) Uani 0.311(8) 1 d PU A 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 C1 0.0461(17) 0.058(2) 0.0419(18) 0.0097(16) 0.0040(13) 0.0045(15) C2 0.0455(17) 0.0365(15) 0.0400(17) 0.0054(13) 0.0073(13) 0.0048(13) C3 0.0279(13) 0.0319(15) 0.0378(14) 0.0025(12) 0.0066(11) 0.0017(11) C4 0.0306(14) 0.0349(15) 0.0430(17) -0.0008(13) 0.0040(12) -0.0002(12) C5 0.0291(15) 0.0445(17) 0.059(2) -0.0122(16) 0.0061(13) -0.0010(13) C6 0.075(3) 0.121(3) 0.041(2) -0.022(2) -0.0001(17) -0.007(2) C7 0.0268(14) 0.0541(19) 0.0383(16) -0.0016(14) 0.0066(11) 0.0019(12) C8 0.0269(13) 0.0395(16) 0.0382(16) 0.0040(13) 0.0085(11) 0.0014(11) C9 0.0258(13) 0.0360(14) 0.0382(16) 0.0026(11) 0.0086(11) 0.0015(11) C10 0.0392(15) 0.0366(16) 0.0420(16) 0.0047(14) 0.0077(12) -0.0007(12) C11 0.0415(16) 0.0336(15) 0.0546(19) 0.0028(14) 0.0085(13) -0.0023(13) C12 0.057(2) 0.057(2) 0.068(2) -0.0226(18) 0.0075(17) -0.0047(17) N1 0.0333(13) 0.0691(18) 0.0391(14) -0.0085(14) 0.0022(10) -0.0008(12) N2 0.0346(13) 0.0414(15) 0.0485(15) -0.0097(12) 0.0075(10) -0.0004(10) B 0.054(2) 0.039(2) 0.045(2) 0.0018(18) -0.0016(17) 0.0061(17) F1A 0.064(4) 0.074(4) 0.084(4) -0.011(3) -0.022(3) 0.029(3) F2A 0.107(5) 0.076(3) 0.042(2) -0.0005(19) 0.006(2) 0.009(3) F3A 0.073(3) 0.130(4) 0.104(3) 0.025(3) 0.037(2) 0.020(3) F4A 0.153(5) 0.050(2) 0.086(3) 0.011(2) -0.045(3) -0.024(2) F1B 0.105(13) 0.053(6) 0.079(6) 0.026(5) -0.017(9) 0.012(8) F2B 0.112(10) 0.091(7) 0.073(9) -0.027(8) -0.051(8) 0.001(7) F3B 0.099(6) 0.096(7) 0.085(5) -0.003(5) 0.018(5) 0.053(5) F4B 0.112(8) 0.118(8) 0.078(6) 0.031(6) 0.004(5) -0.032(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.353(4) . ? C1 N1 1.358(4) . ? C2 C3 1.418(4) . ? C3 C3 1.424(5) 3_656 ? C3 C4 1.428(4) . ? C4 C5 1.344(4) . ? C5 N1 1.360(4) . ? C6 N1 1.465(4) . ? C7 C8 1.354(4) . ? C7 N2 1.359(3) . ? C8 C9 1.428(4) . ? C9 C10 1.424(4) . ? C9 C9 1.427(5) 3_756 ? C10 C11 1.355(4) . ? C11 N2 1.350(4) . ? C12 N2 1.467(4) . ? B F3B 1.301(9) . ? B F1A 1.378(12) . ? B F2B 1.286(18) . ? B F4A 1.361(5) . ? B F2A 1.408(9) . ? B F1B 1.32(3) . ? B F3A 1.395(5) . ? B F4B 1.413(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 121.6(3) . . ? C1 C2 C3 121.8(3) . . ? C2 C3 C3 122.8(3) . 3_656 ? C2 C3 C4 114.6(2) . . ? C3 C3 C4 122.6(3) 3_656 . ? C5 C4 C3 121.0(3) . . ? C4 C5 N1 122.6(3) . . ? C8 C7 N2 122.1(3) . . ? C7 C8 C9 121.2(3) . . ? C10 C9 C9 122.8(3) . 3_756 ? C10 C9 C8 114.6(2) . . ? C9 C9 C8 122.5(3) 3_756 . ? C11 C10 C9 121.1(3) . . ? C10 C11 N2 122.5(3) . . ? C1 N1 C5 118.4(2) . . ? C1 N1 C6 120.7(3) . . ? C5 N1 C6 121.0(3) . . ? C11 N2 C7 118.4(2) . . ? C11 N2 C12 120.5(3) . . ? C7 N2 C12 121.1(3) . . ? F3B B F2B 119.2(12) . . ? F1A B F4A 114.1(7) . . ? F2B B F4A 120.9(11) . . ? F1A B F2A 111.1(8) . . ? F4A B F2A 108.8(5) . . ? F3B B F1B 107.4(15) . . ? F2B B F1B 111.7(19) . . ? F1A B F3A 109.5(6) . . ? F4A B F3A 106.7(4) . . ? F2A B F3A 106.3(5) . . ? F3B B F4B 105.7(8) . . ? F2B B F4B 108.8(10) . . ? F1B B F4B 102.6(13) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.52 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.230 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 951741' ####################################################################### # # 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_(MV)2(BF4)3 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H14 N2), 3(B F4)' _chemical_formula_sum 'C24 H28 B3 F12 N4' _chemical_formula_weight 632.93 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _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 24.767(6) _cell_length_b 10.4678(12) _cell_length_c 12.913(3) _cell_angle_alpha 90.00 _cell_angle_beta 121.425(14) _cell_angle_gamma 90.00 _cell_volume 2856.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1292 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 11081 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0819 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2471 _reflns_number_gt 1371 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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. One of the three BF4- anions in the structure is disordered over two positions with 50% occupancies about a twofold axis. To refine the corresponding disordered B and F atoms anisotropically, SAME, DELU and ISOR restraints were applied. The crystal is twinned by 180 degrees rotation about [001] direct lattice axis. Corresponding twin law is (-1 0 -2, 0 -1 0, 0 0 1) and refined twin fraction is 0.487(3). ; _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^)+(0.0924P)^2^+0.3480P] 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 2471 _refine_ls_number_parameters 220 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.1464 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1706 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.08514(18) 0.2896(3) 0.5938(4) 0.0372(10) Uani 1 1 d . . . C1 C 0.1203(3) 0.4111(5) 0.6319(7) 0.0595(17) Uani 1 1 d . . . H1A H 0.1199 0.4494 0.5640 0.071 Uiso 1 1 calc R . . H1B H 0.1632 0.3952 0.6955 0.071 Uiso 1 1 calc R . . H1C H 0.1006 0.4679 0.6609 0.071 Uiso 1 1 calc R . . C2 C 0.1154(2) 0.1781(4) 0.6128(5) 0.0385(12) Uani 1 1 d . . . H2 H 0.1592 0.1780 0.6498 0.046 Uiso 1 1 calc R . . C3 C 0.0834(2) 0.0631(4) 0.5790(5) 0.0317(11) Uani 1 1 d . . . H3 H 0.1058 -0.0129 0.5958 0.038 Uiso 1 1 calc R . . C4 C 0.01769(18) 0.0602(4) 0.5198(4) 0.0246(9) Uani 1 1 d . . . C5 C -0.0130(2) 0.1783(4) 0.5000(4) 0.0313(12) Uani 1 1 d . . . H5 H -0.0569 0.1817 0.4602 0.038 Uiso 1 1 calc R . . C6 C 0.0217(2) 0.2882(5) 0.5394(5) 0.0391(14) Uani 1 1 d . . . H6 H 0.0007 0.3653 0.5281 0.047 Uiso 1 1 calc R . . N2 N 0.16707(18) 0.0161(4) 0.4085(5) 0.0356(10) Uani 1 1 d . . . C7 C 0.2372(2) 0.0144(6) 0.4795(7) 0.0499(14) Uani 1 1 d . . . H7A H 0.2523 0.0496 0.5586 0.060 Uiso 1 1 calc PR . . H7B H 0.2529 0.0645 0.4384 0.060 Uiso 1 1 calc R . . H7C H 0.2519 -0.0720 0.4873 0.060 Uiso 1 1 calc R . . C8 C 0.1342(3) 0.1256(5) 0.3680(6) 0.0423(16) Uani 1 1 d . . . H8 H 0.1559 0.2023 0.3822 0.051 Uiso 1 1 calc R . . C9 C 0.0705(3) 0.1265(5) 0.3072(5) 0.0355(14) Uani 1 1 d . . . H9 H 0.0499 0.2046 0.2802 0.043 Uiso 1 1 calc R . . C10 C 0.0332(2) 0.0151(4) 0.2822(6) 0.0270(9) Uani 1 1 d . . . C11 C 0.0705(3) -0.1016(4) 0.3246(5) 0.0345(13) Uani 1 1 d . . . H11 H 0.0500 -0.1801 0.3087 0.041 Uiso 1 1 calc R . . C12 C 0.1344(3) -0.0975(4) 0.3869(5) 0.0327(13) Uani 1 1 d . . . H12 H 0.1571 -0.1732 0.4160 0.039 Uiso 1 1 calc R . . B1 B 0.2109(3) 0.2342(6) 0.1961(7) 0.0499(17) Uani 1 1 d D . . F1 F 0.20226(17) 0.1063(3) 0.1935(4) 0.0788(11) Uani 1 1 d D . . F2 F 0.2488(2) 0.2613(4) 0.1487(3) 0.0615(10) Uani 1 1 d D . . F3 F 0.15275(19) 0.2919(4) 0.1258(6) 0.129(3) Uani 1 1 d D . . F4 F 0.2402(2) 0.2762(4) 0.3139(4) 0.0769(15) Uani 1 1 d D . . B3 B -0.0142(6) 0.5008(11) 0.2355(17) 0.052(3) Uani 0.50 1 d PDU . . F9A F -0.0105(7) 0.4373(17) 0.1552(15) 0.085(4) Uani 0.50 1 d PDU . . F10A F -0.0148(7) 0.4356(16) 0.3222(16) 0.079(4) Uani 0.50 1 d PDU . . F11A F -0.0703(5) 0.5690(10) 0.1754(13) 0.125(4) Uani 0.50 1 d PDU . . F12A F 0.0253(4) 0.6097(7) 0.2748(11) 0.094(3) Uani 0.50 1 d PDU . . 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 N1 0.042(3) 0.037(2) 0.033(3) 0.000(2) 0.020(2) -0.0050(17) C1 0.065(4) 0.048(3) 0.076(5) -0.020(3) 0.044(4) -0.028(3) C2 0.025(3) 0.054(3) 0.030(3) -0.005(3) 0.010(3) -0.004(2) C3 0.033(3) 0.036(2) 0.025(3) -0.004(3) 0.014(3) 0.0019(19) C4 0.025(3) 0.035(2) 0.013(3) -0.001(2) 0.010(3) 0.0059(15) C5 0.032(3) 0.034(3) 0.032(3) 0.007(2) 0.019(3) 0.0014(19) C6 0.038(3) 0.043(3) 0.038(3) 0.007(2) 0.022(3) 0.007(2) N2 0.038(2) 0.038(2) 0.032(3) -0.010(2) 0.019(3) -0.005(2) C7 0.038(3) 0.057(4) 0.043(4) -0.010(3) 0.013(4) -0.002(3) C8 0.053(5) 0.035(3) 0.038(4) 0.002(3) 0.023(3) 0.004(3) C9 0.043(4) 0.029(3) 0.041(4) 0.000(2) 0.027(3) 0.000(2) C10 0.038(2) 0.021(2) 0.027(4) -0.003(2) 0.020(3) -0.002(2) C11 0.051(4) 0.035(3) 0.027(4) -0.002(3) 0.027(3) -0.003(2) C12 0.046(4) 0.027(3) 0.027(3) 0.003(2) 0.021(3) 0.012(2) B1 0.036(4) 0.057(4) 0.055(5) -0.017(4) 0.023(4) -0.021(3) F1 0.099(3) 0.067(2) 0.078(3) -0.017(2) 0.051(3) -0.0484(19) F2 0.062(2) 0.079(2) 0.045(2) -0.0059(18) 0.029(2) -0.0260(19) F3 0.036(2) 0.108(3) 0.183(6) -0.023(4) 0.016(3) 0.005(2) F4 0.067(3) 0.104(4) 0.078(3) -0.050(2) 0.050(3) -0.042(3) B3 0.072(8) 0.041(5) 0.044(7) -0.007(5) 0.031(7) 0.000(5) F9A 0.121(9) 0.074(7) 0.059(6) -0.028(5) 0.046(6) -0.002(6) F10A 0.104(8) 0.074(6) 0.086(6) 0.002(5) 0.068(7) -0.009(5) F11A 0.095(6) 0.128(7) 0.123(7) 0.007(6) 0.035(6) 0.036(5) F12A 0.123(8) 0.052(4) 0.098(7) -0.006(4) 0.052(7) -0.029(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C2 1.340(6) . ? N1 C6 1.346(6) . ? N1 C1 1.473(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.381(6) . ? C2 H2 0.9300 . ? C3 C4 1.391(6) . ? C3 H3 0.9300 . ? C4 C5 1.403(5) . ? C4 C4 1.467(8) 5_556 ? C5 C6 1.366(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N2 C8 1.344(7) . ? N2 C12 1.382(6) . ? N2 C7 1.483(6) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.346(7) . ? C8 H8 0.9300 . ? C9 C10 1.417(7) . ? C9 H9 0.9300 . ? C10 C10 1.403(8) 2 ? C10 C11 1.455(7) . ? C11 C12 1.353(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? B1 F1 1.353(7) . ? B1 F4 1.372(8) . ? B1 F3 1.378(7) . ? B1 F2 1.392(8) . ? B3 F9A 1.275(16) . ? B3 F10A 1.318(16) . ? B3 F11A 1.384(13) . ? B3 F12A 1.412(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 118.4(4) . . ? C2 N1 C1 121.0(4) . . ? C6 N1 C1 120.6(4) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.8(4) . . ? N1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 116.7(4) . . ? C3 C4 C4 121.7(4) . 5_556 ? C5 C4 C4 121.7(4) . 5_556 ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? N1 C6 C5 122.7(4) . . ? N1 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? C8 N2 C12 118.9(4) . . ? C8 N2 C7 121.9(5) . . ? C12 N2 C7 119.2(5) . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C9 121.4(5) . . ? N2 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C10 123.7(5) . . ? C8 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C10 C10 C9 124.0(3) 2 . ? C10 C10 C11 122.7(3) 2 . ? C9 C10 C11 113.2(4) . . ? C12 C11 C10 120.9(4) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 N2 121.9(4) . . ? C11 C12 H12 119.1 . . ? N2 C12 H12 119.1 . . ? F1 B1 F4 109.3(6) . . ? F1 B1 F3 108.7(5) . . ? F4 B1 F3 110.9(6) . . ? F1 B1 F2 108.9(5) . . ? F4 B1 F2 109.5(4) . . ? F3 B1 F2 109.5(6) . . ? B3 B3 F12A 101.6(7) 2 2 ? B3 B3 F9A 87(4) 2 . ? F12A B3 F9A 122.0(19) 2 . ? B3 B3 F10A 90(4) 2 . ? F12A B3 F10A 119.9(18) 2 . ? F9A B3 F10A 117.2(9) . . ? B3 B3 F9A 67(3) 2 2 ? F12A B3 F9A 123(2) 2 2 ? F9A B3 F9A 113.5(19) . 2 ? B3 B3 F11A 148.9(8) 2 . ? F12A B3 F11A 47.5(7) 2 . ? F9A B3 F11A 106.8(15) . . ? F10A B3 F11A 107.0(15) . . ? F9A B3 F11A 127.0(19) 2 . ? B3 B3 F12A 53.8(6) 2 . ? F12A B3 F12A 47.8(9) 2 . ? F9A B3 F12A 112.5(16) . . ? F10A B3 F12A 115.2(15) . . ? F9A B3 F12A 99.6(12) 2 . ? F11A B3 F12A 95.2(10) . . ? B3 B3 F10A 66(3) 2 2 ? F12A B3 F10A 124(2) 2 2 ? F10A B3 F10A 114.9(18) . 2 ? F9A B3 F10A 102.9(9) 2 2 ? F11A B3 F10A 125.2(18) . 2 ? F12A B3 F10A 97.4(13) . 2 ? F12A B3 F11A 79.8(9) 2 2 ? F9A B3 F11A 99.4(12) . 2 ? F10A B3 F11A 100.0(11) . 2 ? F9A B3 F11A 78.6(9) 2 2 ? F11A B3 F11A 127.2(11) . 2 ? F10A B3 F11A 78.8(9) 2 2 ? F10A F9A B3 98(3) 2 . ? F10A F9A B3 72(3) 2 2 ? F9A F10A B3 85(3) 2 . ? F9A F10A B3 61(2) 2 2 ? F12A F11A B3 55.1(8) 2 . ? F12A F11A B3 45.8(7) 2 2 ? F11A F12A F12A 155.6(9) 2 2 ? F11A F12A B3 77.5(9) 2 2 ? F12A F12A B3 78.4(7) 2 2 ? F11A F12A B3 102.1(10) 2 . ? F12A F12A B3 53.8(6) 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 -0.5(9) . . . . ? C1 N1 C2 C3 179.2(6) . . . . ? N1 C2 C3 C4 2.2(10) . . . . ? C2 C3 C4 C5 -1.6(9) . . . . ? C2 C3 C4 C4 178.5(6) . . . 5_556 ? C3 C4 C5 C6 -0.6(8) . . . . ? C4 C4 C5 C6 179.4(6) 5_556 . . . ? C2 N1 C6 C5 -1.8(9) . . . . ? C1 N1 C6 C5 178.5(5) . . . . ? C4 C5 C6 N1 2.4(9) . . . . ? C12 N2 C8 C9 0.1(10) . . . . ? C7 N2 C8 C9 -177.7(7) . . . . ? N2 C8 C9 C10 0.7(10) . . . . ? C8 C9 C10 C10 -179.3(8) . . . 2 ? C8 C9 C10 C11 -2.3(10) . . . . ? C10 C10 C11 C12 -179.7(7) 2 . . . ? C9 C10 C11 C12 3.2(10) . . . . ? C10 C11 C12 N2 -2.7(10) . . . . ? C8 N2 C12 C11 1.0(10) . . . . ? C7 N2 C12 C11 178.8(7) . . . . ? B3 B3 F9A F10A -1(5) 2 . . 2 ? F12A B3 F9A F10A 101(4) 2 . . 2 ? F10A B3 F9A F10A -89(5) . . . 2 ? F9A B3 F9A F10A -64(5) 2 . . 2 ? F11A B3 F9A F10A 151(4) . . . 2 ? F12A B3 F9A F10A 48(5) . . . 2 ? F11A B3 F9A F10A 17(5) 2 . . 2 ? F12A B3 F9A B3 102(3) 2 . . 2 ? F10A B3 F9A B3 -88(2) . . . 2 ? F9A B3 F9A B3 -63.5(19) 2 . . 2 ? F11A B3 F9A B3 152(3) . . . 2 ? F12A B3 F9A B3 48.6(19) . . . 2 ? F10A B3 F9A B3 1(5) 2 . . 2 ? F11A B3 F9A B3 18.0(18) 2 . . 2 ? B3 B3 F10A F9A -1(4) 2 . . 2 ? F12A B3 F10A F9A -104(4) 2 . . 2 ? F9A B3 F10A F9A 86(4) . . . 2 ? F11A B3 F10A F9A -154(4) . . . 2 ? F12A B3 F10A F9A -50(5) . . . 2 ? F10A B3 F10A F9A 62(5) 2 . . 2 ? F11A B3 F10A F9A -20(4) 2 . . 2 ? F12A B3 F10A B3 -103(2) 2 . . 2 ? F9A B3 F10A B3 87(2) . . . 2 ? F9A B3 F10A B3 1(4) 2 . . 2 ? F11A B3 F10A B3 -154(3) . . . 2 ? F12A B3 F10A B3 -49(2) . . . 2 ? F10A B3 F10A B3 63(2) 2 . . 2 ? F11A B3 F10A B3 -19.4(19) 2 . . 2 ? B3 B3 F11A F12A -5(9) 2 . . 2 ? F9A B3 F11A F12A -118.4(19) . . . 2 ? F10A B3 F11A F12A 115.3(18) . . . 2 ? F9A B3 F11A F12A 103(2) 2 . . 2 ? F12A B3 F11A F12A -3.0(18) . . . 2 ? F10A B3 F11A F12A -106(2) 2 . . 2 ? F11A B3 F11A F12A -2.1(14) 2 . . 2 ? F12A B3 F11A B3 5(9) 2 . . 2 ? F9A B3 F11A B3 -113(10) . . . 2 ? F10A B3 F11A B3 120(10) . . . 2 ? F9A B3 F11A B3 108(10) 2 . . 2 ? F12A B3 F11A B3 2(9) . . . 2 ? F10A B3 F11A B3 -101(10) 2 . . 2 ? F11A B3 F11A B3 3(8) 2 . . 2 ? B3 B3 F12A F11A -3(5) 2 . . 2 ? F12A B3 F12A F11A 176(3) 2 . . 2 ? F9A B3 F12A F11A -71(2) . . . 2 ? F10A B3 F12A F11A 67(2) . . . 2 ? F9A B3 F12A F11A 49.7(19) 2 . . 2 ? F11A B3 F12A F11A 178.7(13) . . . 2 ? F10A B3 F12A F11A -54.8(19) 2 . . 2 ? B3 B3 F12A F12A -178(6) 2 . . 2 ? F9A B3 F12A F12A 114(2) . . . 2 ? F10A B3 F12A F12A -109(2) . . . 2 ? F9A B3 F12A F12A -126(2) 2 . . 2 ? F11A B3 F12A F12A 3.0(18) . . . 2 ? F10A B3 F12A F12A 129(2) 2 . . 2 ? F11A B3 F12A F12A -176(3) 2 . . 2 ? F12A B3 F12A B3 178(6) 2 . . 2 ? F9A B3 F12A B3 -68(4) . . . 2 ? F10A B3 F12A B3 70(4) . . . 2 ? F9A B3 F12A B3 52(4) 2 . . 2 ? F11A B3 F12A B3 -179(5) . . . 2 ? F10A B3 F12A B3 -52(4) 2 . . 2 ? F11A B3 F12A B3 3(5) 2 . . 2 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.379 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 951742' ####################################################################### # # 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_MV(BF4)2 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2, 2(B F4)' _chemical_formula_sum 'C12 H14 B2 F8 N2' _chemical_formula_weight 359.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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 5.76040(10) _cell_length_b 8.86460(10) _cell_length_c 14.8902(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.975(2) _cell_angle_gamma 90.00 _cell_volume 757.483(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 6753 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1749 _reflns_number_gt 818 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0645P)^2^+0.4546P] 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 1749 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1559 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5388(4) 0.2603(3) 0.42391(16) 0.0427(7) Uani 1 1 d . . . C1 C 0.3473(6) 0.1579(4) 0.3917(2) 0.0592(10) Uani 1 1 d . . . H1A H 0.2418 0.2098 0.3488 0.089 Uiso 1 1 calc R . . H1B H 0.2654 0.1258 0.4418 0.089 Uiso 1 1 calc R . . H1C H 0.4102 0.0714 0.3635 0.089 Uiso 1 1 calc R . . C2 C 0.5933(6) 0.2809(4) 0.5124(2) 0.0536(9) Uani 1 1 d . . . H2 H 0.5083 0.2306 0.5535 0.064 Uiso 1 1 calc R . . C3 C 0.7710(6) 0.3742(4) 0.54338(19) 0.0509(9) Uani 1 1 d . . . H3 H 0.8047 0.3872 0.6051 0.061 Uiso 1 1 calc R . . C4 C 0.9015(5) 0.4496(3) 0.48391(17) 0.0377(7) Uani 1 1 d . . . C5 C 0.8396(6) 0.4264(4) 0.39260(19) 0.0468(8) Uani 1 1 d . . . H5 H 0.9218 0.4756 0.3502 0.056 Uiso 1 1 calc R . . C6 C 0.6605(6) 0.3328(4) 0.3644(2) 0.0496(9) Uani 1 1 d . . . H6 H 0.6220 0.3189 0.3030 0.060 Uiso 1 1 calc R . . B1 B 0.8510(7) -0.0940(5) 0.3248(2) 0.0487(10) Uani 1 1 d . . . F3 F 1.0785(4) -0.1245(3) 0.31241(14) 0.0805(8) Uani 1 1 d . . . F4 F 0.7221(5) -0.2249(3) 0.32444(16) 0.0940(9) Uani 1 1 d . . . F1 F 0.8351(4) -0.0238(3) 0.40657(14) 0.0893(9) Uani 1 1 d . . . F2 F 0.7575(4) -0.0032(3) 0.25592(13) 0.0838(8) 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 N1 0.0448(15) 0.0399(16) 0.0441(15) 0.0015(11) 0.0087(12) 0.0086(12) C1 0.051(2) 0.063(3) 0.063(2) 0.0004(18) 0.0053(17) -0.0057(19) C2 0.071(2) 0.054(2) 0.0380(18) 0.0082(15) 0.0162(16) -0.001(2) C3 0.069(2) 0.055(2) 0.0292(15) 0.0061(14) 0.0072(15) -0.006(2) C4 0.0473(17) 0.0368(18) 0.0298(15) 0.0024(12) 0.0082(12) 0.0130(14) C5 0.051(2) 0.059(2) 0.0319(17) 0.0047(14) 0.0123(14) 0.0006(18) C6 0.052(2) 0.064(2) 0.0338(16) 0.0021(15) 0.0089(15) 0.0013(18) B1 0.048(2) 0.060(3) 0.038(2) 0.0028(18) 0.0088(16) 0.002(2) F3 0.0607(14) 0.114(2) 0.0690(14) 0.0154(12) 0.0193(10) 0.0189(14) F4 0.113(2) 0.0811(17) 0.0901(17) 0.0022(13) 0.0224(14) -0.0381(16) F1 0.0974(18) 0.120(2) 0.0517(12) -0.0249(12) 0.0112(11) 0.0081(15) F2 0.0879(16) 0.1015(19) 0.0629(13) 0.0324(12) 0.0115(12) 0.0214(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C2 1.340(4) . ? N1 C6 1.341(4) . ? N1 C1 1.476(4) . ? C2 C3 1.365(5) . ? C3 C4 1.383(4) . ? C4 C5 1.391(4) . ? C4 C4 1.491(6) 3_766 ? C5 C6 1.362(5) . ? B1 F3 1.366(4) . ? B1 F2 1.376(4) . ? B1 F1 1.378(4) . ? B1 F4 1.378(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 119.6(3) . . ? C2 N1 C1 120.5(3) . . ? C6 N1 C1 119.9(3) . . ? N1 C2 C3 121.3(3) . . ? C2 C3 C4 120.7(3) . . ? C3 C4 C5 116.6(3) . . ? C3 C4 C4 121.7(3) . 3_766 ? C5 C4 C4 121.8(3) . 3_766 ? C6 C5 C4 121.0(3) . . ? N1 C6 C5 120.9(3) . . ? F3 B1 F2 109.5(3) . . ? F3 B1 F1 110.3(3) . . ? F2 B1 F1 110.1(3) . . ? F3 B1 F4 110.8(3) . . ? F2 B1 F4 108.3(3) . . ? F1 B1 F4 107.8(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.281 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 959361'