# Electronic Supplementary Material (ESI) for RSC Advances # 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_1 _database_code_depnum_ccdc_archive 'CCDC 896712' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 B Cl4 F2 N2 O' _chemical_formula_weight 359.77 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' Cl Cl 0.1484 0.1585 '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 9.8376(14) _cell_length_b 9.1284(12) _cell_length_c 15.0458(19) _cell_angle_alpha 90.00 _cell_angle_beta 95.922(9) _cell_angle_gamma 90.00 _cell_volume 1343.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1875 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.12 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.896 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7960 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2353 _reflns_number_gt 1939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.5438P] 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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2353 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Cl1 Cl 0.36801(8) 0.10853(8) 0.04824(6) 0.0730(3) Uani 1 1 d . . . Cl2 Cl 0.45742(9) 0.20598(10) -0.15338(5) 0.0756(3) Uani 1 1 d . . . Cl3 Cl 0.88265(9) 0.65025(11) -0.23623(5) 0.0816(3) Uani 1 1 d . . . Cl4 Cl 1.07250(9) 0.86380(10) -0.08610(7) 0.0832(3) Uani 1 1 d . . . F1 F 0.61223(17) 0.4930(2) -0.18844(10) 0.0747(5) Uani 1 1 d . . . F2 F 0.77893(19) 0.3233(2) -0.16024(12) 0.0762(5) Uani 1 1 d . . . C1 C 0.5296(3) 0.2706(3) -0.05386(18) 0.0540(7) Uani 1 1 d . . . C2 C 0.4944(3) 0.2300(3) 0.02981(19) 0.0535(6) Uani 1 1 d . . . C3 C 0.5780(3) 0.3053(3) 0.09236(18) 0.0546(7) Uani 1 1 d . . . H3A H 0.5783 0.2989 0.1541 0.066 Uiso 1 1 calc R . . C4 C 0.6634(3) 0.3939(3) 0.04567(16) 0.0466(6) Uani 1 1 d . . . C5 C 0.7658(3) 0.4970(3) 0.07182(15) 0.0472(6) Uani 1 1 d . . . C6 C 0.8326(3) 0.5771(3) 0.00832(16) 0.0471(6) Uani 1 1 d . . . C7 C 0.9305(3) 0.6870(3) 0.02289(19) 0.0536(6) Uani 1 1 d . . . H7A H 0.9677 0.7241 0.0776 0.064 Uiso 1 1 calc R . . C8 C 0.9610(3) 0.7295(3) -0.0612(2) 0.0569(7) Uani 1 1 d . . . C9 C 0.8836(3) 0.6459(3) -0.12329(18) 0.0547(7) Uani 1 1 d . . . C10 C 0.7596(4) 0.4658(4) 0.23186(18) 0.0718(9) Uani 1 1 d . . . H10A H 0.8064 0.5070 0.2852 0.108 Uiso 1 1 calc R . . H10B H 0.7750 0.3620 0.2311 0.108 Uiso 1 1 calc R . . H10C H 0.6634 0.4847 0.2306 0.108 Uiso 1 1 calc R . . O1 O 0.8108(2) 0.5318(2) 0.15461(11) 0.0584(5) Uani 1 1 d . . . N1 N 0.6307(2) 0.3695(2) -0.04600(13) 0.0477(5) Uani 1 1 d . . . N2 N 0.8037(2) 0.5518(2) -0.08242(13) 0.0488(5) Uani 1 1 d . . . B1 B 0.7059(3) 0.4336(4) -0.12447(19) 0.0537(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 Cl1 0.0602(5) 0.0552(4) 0.1051(7) 0.0051(4) 0.0156(4) 0.0049(3) Cl2 0.0762(5) 0.0789(5) 0.0668(5) -0.0089(4) -0.0159(4) 0.0018(4) Cl3 0.0859(6) 0.1090(7) 0.0521(4) 0.0217(4) 0.0174(4) 0.0118(5) Cl4 0.0732(5) 0.0690(5) 0.1108(7) 0.0198(5) 0.0266(5) 0.0005(4) F1 0.0702(11) 0.1025(14) 0.0490(9) 0.0186(9) -0.0055(8) 0.0063(10) F2 0.0798(12) 0.0772(11) 0.0738(11) -0.0286(9) 0.0178(9) 0.0112(9) C1 0.0557(16) 0.0480(15) 0.0561(16) -0.0034(12) -0.0045(12) 0.0154(13) C2 0.0508(14) 0.0410(14) 0.0689(17) 0.0011(12) 0.0071(13) 0.0109(12) C3 0.0647(17) 0.0501(15) 0.0507(15) 0.0030(12) 0.0138(13) 0.0142(13) C4 0.0547(15) 0.0417(13) 0.0436(13) 0.0016(10) 0.0061(11) 0.0124(11) C5 0.0576(15) 0.0437(13) 0.0404(13) 0.0002(10) 0.0066(11) 0.0149(12) C6 0.0532(14) 0.0456(14) 0.0431(13) 0.0008(11) 0.0078(11) 0.0150(12) C7 0.0537(15) 0.0475(15) 0.0600(16) -0.0001(12) 0.0072(12) 0.0120(13) C8 0.0518(15) 0.0513(15) 0.0694(18) 0.0108(13) 0.0142(13) 0.0144(13) C9 0.0571(16) 0.0575(16) 0.0513(15) 0.0144(12) 0.0147(13) 0.0204(13) C10 0.091(2) 0.087(2) 0.0380(14) 0.0041(14) 0.0083(14) -0.0092(19) O1 0.0762(13) 0.0602(11) 0.0388(9) -0.0025(8) 0.0064(9) -0.0020(10) N1 0.0540(13) 0.0451(12) 0.0430(11) 0.0008(9) 0.0000(9) 0.0112(10) N2 0.0546(12) 0.0505(12) 0.0422(11) 0.0049(9) 0.0085(9) 0.0150(10) B1 0.0569(18) 0.0622(19) 0.0418(15) -0.0003(14) 0.0043(13) 0.0171(15) _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 Cl1 C2 1.710(3) . ? Cl2 C1 1.696(3) . ? Cl3 C9 1.699(3) . ? Cl4 C8 1.712(3) . ? F1 B1 1.374(3) . ? F2 B1 1.378(3) . ? C1 N1 1.339(4) . ? C1 C2 1.390(4) . ? C2 C3 1.369(4) . ? C3 C4 1.405(4) . ? C3 H3A 0.9300 . ? C4 N1 1.401(3) . ? C4 C5 1.405(4) . ? C5 O1 1.317(3) . ? C5 C6 1.417(4) . ? C6 N2 1.385(3) . ? C6 C7 1.392(4) . ? C7 C8 1.385(4) . ? C7 H7A 0.9300 . ? C8 C9 1.374(4) . ? C9 N2 1.354(3) . ? C10 O1 1.445(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N1 B1 1.570(4) . ? N2 B1 1.538(4) . ? 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 110.6(2) . . ? N1 C1 Cl2 123.5(2) . . ? C2 C1 Cl2 125.9(2) . . ? C3 C2 C1 107.5(2) . . ? C3 C2 Cl1 127.5(2) . . ? C1 C2 Cl1 125.0(2) . . ? C2 C3 C4 107.0(2) . . ? C2 C3 H3A 126.5 . . ? C4 C3 H3A 126.5 . . ? N1 C4 C3 108.2(2) . . ? N1 C4 C5 117.9(2) . . ? C3 C4 C5 133.9(2) . . ? O1 C5 C4 126.0(2) . . ? O1 C5 C6 112.3(2) . . ? C4 C5 C6 121.7(2) . . ? N2 C6 C7 110.1(2) . . ? N2 C6 C5 121.1(2) . . ? C7 C6 C5 128.8(2) . . ? C8 C7 C6 105.6(3) . . ? C8 C7 H7A 127.2 . . ? C6 C7 H7A 127.2 . . ? C9 C8 C7 108.0(3) . . ? C9 C8 Cl4 124.8(2) . . ? C7 C8 Cl4 127.2(2) . . ? N2 C9 C8 110.5(2) . . ? N2 C9 Cl3 121.7(2) . . ? C8 C9 Cl3 127.8(2) . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 O1 C10 123.3(2) . . ? C1 N1 C4 106.7(2) . . ? C1 N1 B1 126.0(2) . . ? C4 N1 B1 127.1(2) . . ? C9 N2 C6 105.8(2) . . ? C9 N2 B1 128.8(2) . . ? C6 N2 B1 125.4(2) . . ? F1 B1 F2 110.7(2) . . ? F1 B1 N2 110.9(2) . . ? F2 B1 N2 110.1(2) . . ? F1 B1 N1 109.8(2) . . ? F2 B1 N1 109.1(2) . . ? N2 B1 N1 106.0(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.544 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.050