#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:16:59 +0300 (Thu, 07 May 2020) $ #$Revision: 251828 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240464.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240464 loop_ _publ_author_name 'Wallis, John D.' 'Garner, Alun Christopher' 'Yang, Songjie' _publ_section_title ; N-H···O Hydrogen Bonding to the Alkoxy Oxygen of a Carboxylic Ester Group: Crystal Structures of Methyl 2,6-Diaminobenzoate and Its Derivatives. ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00495B _journal_year 2020 _chemical_formula_sum 'C8 H12 B2 F8 N2 O2' _chemical_formula_weight 341.82 _chemical_melting_point 484.0(10) _chemical_name_systematic ; Methyl2,6-dinitrobenzoate bis HBF4 salt ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014 _audit_update_record ; 2020-04-01 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.379(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.1001(4) _cell_length_b 10.8475(7) _cell_length_c 16.4165(11) _cell_measurement_reflns_used 2362 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.2360 _cell_measurement_theta_min 4.1030 _cell_volume 1260.68(14) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SHELXS-97 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9832 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.855 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.0467 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.855 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6957 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.855 _diffrn_reflns_theta_full 27.000 _diffrn_reflns_theta_max 29.372 _diffrn_reflns_theta_min 3.047 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'pale brown' _exptl_crystal_density_diffrn 1.801 _exptl_crystal_description 'thick plate' _exptl_crystal_F_000 688 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile' _exptl_crystal_size_max 0.3349 _exptl_crystal_size_mid 0.1509 _exptl_crystal_size_min 0.1331 _refine_diff_density_max 0.294 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 2966 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.109 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0440 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.2125P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.0884 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2368 _reflns_number_total 2966 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00495b2.cif _cod_data_source_block bf4absH _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '483-485' was changed to '484.0(10)' -- the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240464 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2014-3 _shelx_res_file ; REM P2(1)/n (#14 in standard setting) REM diaminoesterBF4AA in P2(1)/n REM R1 = 0.0438 for 2368 Fo > 4sig(Fo) and 0.0623 for all 2966 data REM 247 parameters refined using 0 restraints REM Highest difference peak 0.307, deepest hole -0.252, 1-sigma level 0.060 REM diaminoesterBF4AA in P2(1)/n REM R1 = 0.0438 for 2368 Fo > 4sig(Fo) and 0.0623 for all 2966 data REM 247 parameters refined using 0 restraints REM Highest difference peak 0.296, deepest hole -0.254, 1-sigma level 0.060 REM diaminoesterBF4AA in P2(1)/n REM R1 = 0.0438 for 2368 Fo > 4sig(Fo) and 0.0623 for all 2966 data REM 247 parameters refined using 0 restraints REM Highest difference peak 0.296, deepest hole -0.254, 1-sigma level 0.060 REM diaminoesterBF4AA in P2(1)/n REM R1 = 0.0440 for 2368 Fo > 4sig(Fo) and 0.0625 for all 2966 data REM 224 parameters refined using 0 restraints REM Highest difference peak 0.294, deepest hole -0.259, 1-sigma level 0.060 TITL diaminoesterBF4AA in P2(1)/n CELL 0.71073 7.1001 10.8475 16.4165 90.000 94.379 90.000 ZERR 4.0000 0.0004 0.0007 0.0011 0.000 0.006 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H B N O F UNIT 32 48 8 8 8 32 MERG 2 FMAP 2 GRID PLAN 20 TEMP -173 CONF BOND $H 1.0 MPLA 6 C1 C2 C3 C4 C5 C6 N1 N2 C7 MPLA 4 O1 O2 C7 C8 EQIV $1 -x+1, -y+1, -z EQIV $2 -x+1/2, y-1/2, -z-1/2 EQIV $3 x-1, y, z EQIV $4 x-1/2, -y+1/2, z-1/2 EQIV $5 x-3/2, -y+1/2, z-1/2 HTAB C8 F6_$1 HTAB N2 F2_$2 HTAB N2 F3_$2 HTAB N1 F1 HTAB N1 F5_$3 HTAB N2 F1_$4 HTAB N2 F7_$4 HTAB N2 O2 HTAB N2 F5_$5 HTAB N2 F6_$5 HTAB N1 F5_$1 HTAB N1 F8_$1 HTAB N1 F3_$3 HTAB N1 F4_$3 L.S. 4 ACTA 54 WGHT 0.031500 0.212500 FVAR 6.06026 F1 6 0.417159 0.301714 0.018714 11.00000 0.01726 0.02126 = 0.01392 0.00035 0.00358 -0.00215 F2 6 0.424079 0.347020 -0.116206 11.00000 0.01619 0.02078 = 0.01731 0.00521 -0.00150 -0.00164 F3 6 0.668377 0.406826 -0.027087 11.00000 0.01373 0.01868 = 0.02158 -0.00096 0.00105 -0.00295 F4 6 0.628575 0.203442 -0.056605 11.00000 0.02329 0.01706 = 0.02421 -0.00248 0.00053 0.00684 F5 6 1.074281 0.387679 0.093521 11.00000 0.01899 0.03126 = 0.01878 -0.00819 0.00593 -0.00229 F6 6 1.061414 0.321458 0.223110 11.00000 0.02945 0.02449 = 0.02198 0.00177 -0.01038 0.00698 F7 6 0.821147 0.272771 0.128111 11.00000 0.02200 0.01433 = 0.03637 -0.00027 -0.00735 -0.00531 F8 6 0.855779 0.469868 0.171460 11.00000 0.01326 0.01316 = 0.02267 0.00075 0.00394 0.00196 O1 5 -0.196601 0.395275 -0.209446 11.00000 0.01197 0.01304 = 0.01307 -0.00294 -0.00017 0.00138 O2 5 -0.046539 0.332609 -0.318179 11.00000 0.01601 0.01212 = 0.01051 0.00241 0.00137 0.00324 N1 4 0.028366 0.335647 -0.072880 11.00000 0.01112 0.01368 = 0.01146 -0.00066 -0.00040 0.00192 N2 4 -0.035692 0.083578 -0.325739 11.00000 0.00954 0.01097 = 0.01261 -0.00184 0.00002 0.00010 C1 1 -0.012286 0.211576 -0.199805 11.00000 0.00489 0.01091 = 0.01331 -0.00053 0.00199 -0.00188 C2 1 0.041617 0.218067 -0.116066 11.00000 0.00770 0.01098 = 0.01302 -0.00248 0.00119 -0.00060 C3 1 0.115183 0.118147 -0.072709 11.00000 0.01022 0.01548 = 0.01137 0.00120 -0.00074 -0.00143 AFIX 43 H3 2 0.150713 0.125548 -0.015947 11.00000 -1.20000 AFIX 0 C4 1 0.137126 0.006857 -0.112222 11.00000 0.01122 0.01124 = 0.01683 0.00337 -0.00070 0.00048 AFIX 43 H4 2 0.186118 -0.062657 -0.082451 11.00000 -1.20000 AFIX 0 C5 1 0.087498 -0.002941 -0.195264 11.00000 0.00968 0.00992 = 0.01683 -0.00202 0.00310 -0.00070 AFIX 43 H5 2 0.102929 -0.078964 -0.222702 11.00000 -1.20000 AFIX 0 C6 1 0.015447 0.098538 -0.237894 11.00000 0.00683 0.01268 = 0.00987 -0.00104 0.00023 -0.00143 C7 1 -0.097986 0.323150 -0.242311 11.00000 0.00926 0.00949 = 0.01157 -0.00208 -0.00125 -0.00364 C8 1 -0.111367 0.442189 -0.363095 11.00000 0.01960 0.01550 = 0.01216 0.00375 -0.00020 0.00315 AFIX 137 H8A 2 -0.249772 0.443582 -0.368325 11.00000 -1.50000 H8B 2 -0.063808 0.440915 -0.417580 11.00000 -1.50000 H8C 2 -0.064189 0.515882 -0.333633 11.00000 -1.50000 AFIX 0 B1 3 0.535532 0.312898 -0.045092 11.00000 0.01378 0.01431 = 0.01346 0.00275 0.00065 0.00082 B2 3 0.951623 0.360186 0.155149 11.00000 0.01246 0.01357 = 0.01636 -0.00095 -0.00062 0.00054 H11 2 -0.086216 0.353148 -0.065381 11.00000 0.02389 H12 2 0.076434 0.400815 -0.104308 11.00000 0.02899 H13 2 0.093043 0.333178 -0.024355 11.00000 0.02289 H21 2 -0.167739 0.088083 -0.338342 11.00000 0.03363 H22 2 0.020650 0.141348 -0.356685 11.00000 0.03287 H23 2 0.004529 0.007088 -0.341705 11.00000 0.02617 HKLF 4 REM diaminoesterBF4AA in P2(1)/n REM R1 = 0.0440 for 2368 Fo > 4sig(Fo) and 0.0625 for all 2966 data REM 224 parameters refined using 0 restraints END WGHT 0.0314 0.2125 REM Highest difference peak 0.294, deepest hole -0.259, 1-sigma level 0.060 Q1 1 0.0478 0.1660 -0.2233 11.00000 0.05 0.29 Q2 1 0.0571 0.2239 -0.1645 11.00000 0.05 0.26 Q3 1 0.8705 0.2541 0.0819 11.00000 0.05 0.25 Q4 1 1.1642 0.4408 0.1424 11.00000 0.05 0.25 Q5 1 -0.1010 0.1629 -0.2195 11.00000 0.05 0.25 Q6 1 -0.0216 0.1386 -0.2088 11.00000 0.05 0.24 Q7 1 -0.2553 0.4580 -0.2244 11.00000 0.05 0.23 Q8 1 1.1316 0.3172 0.1045 11.00000 0.05 0.22 Q9 1 0.1816 0.0101 -0.1578 11.00000 0.05 0.21 Q10 1 0.0953 0.0660 -0.2188 11.00000 0.05 0.21 Q11 1 0.5848 0.2626 -0.0507 11.00000 0.05 0.21 Q12 1 -0.0417 0.2020 -0.1558 11.00000 0.05 0.21 Q13 1 0.6941 0.2843 0.1709 11.00000 0.05 0.21 Q14 1 0.4082 0.2130 0.0307 11.00000 0.05 0.21 Q15 1 -0.0176 0.2838 -0.2114 11.00000 0.05 0.21 Q16 1 0.1403 0.1784 -0.1032 11.00000 0.05 0.19 Q17 1 1.1355 0.4202 0.2123 11.00000 0.05 0.19 Q18 1 0.2509 0.3294 -0.1670 11.00000 0.05 0.19 Q19 1 0.7363 0.4727 -0.0381 11.00000 0.05 0.19 Q20 1 -0.1000 0.3838 -0.2265 11.00000 0.05 0.19 ; _shelx_res_checksum 84236 loop_ _space_group_symop_operation_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' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.41716(14) 0.30171(9) 0.01871(6) 0.0174(3) Uani 1 1 d . . . . . F2 F 0.42408(14) 0.34702(9) -0.11621(6) 0.0182(3) Uani 1 1 d . . . . . F3 F 0.66838(14) 0.40683(9) -0.02709(7) 0.0180(3) Uani 1 1 d . . . . . F4 F 0.62858(15) 0.20344(9) -0.05661(7) 0.0216(3) Uani 1 1 d . . . . . F5 F 1.07428(15) 0.38768(10) 0.09352(7) 0.0228(3) Uani 1 1 d . . . . . F6 F 1.06141(16) 0.32146(10) 0.22311(7) 0.0259(3) Uani 1 1 d . . . . . F7 F 0.82115(15) 0.27277(9) 0.12811(7) 0.0247(3) Uani 1 1 d . . . . . F8 F 0.85578(14) 0.46987(9) 0.17146(7) 0.0162(2) Uani 1 1 d . . . . . O1 O -0.19660(16) 0.39527(10) -0.20945(7) 0.0128(3) Uani 1 1 d . . . . . O2 O -0.04654(17) 0.33261(10) -0.31818(7) 0.0129(3) Uani 1 1 d . . . . . N1 N 0.0284(2) 0.33565(14) -0.07288(11) 0.0121(3) Uani 1 1 d . . . . . N2 N -0.0357(2) 0.08358(14) -0.32574(10) 0.0111(3) Uani 1 1 d . . . . . C1 C -0.0123(2) 0.21158(15) -0.19980(11) 0.0096(4) Uani 1 1 d . . . . . C2 C 0.0416(2) 0.21807(15) -0.11607(11) 0.0105(4) Uani 1 1 d . . . . . C3 C 0.1152(2) 0.11815(15) -0.07271(11) 0.0124(4) Uani 1 1 d . . . . . H3 H 0.1507 0.1255 -0.0159 0.015 Uiso 1 1 calc R U . . . C4 C 0.1371(2) 0.00686(16) -0.11222(11) 0.0132(4) Uani 1 1 d . . . . . H4 H 0.1861 -0.0627 -0.0825 0.016 Uiso 1 1 calc R U . . . C5 C 0.0875(2) -0.00294(15) -0.19526(12) 0.0120(4) Uani 1 1 d . . . . . H5 H 0.1029 -0.0790 -0.2227 0.014 Uiso 1 1 calc R U . . . C6 C 0.0154(2) 0.09854(15) -0.23789(11) 0.0098(4) Uani 1 1 d . . . . . C7 C -0.0980(2) 0.32315(15) -0.24231(11) 0.0102(4) Uani 1 1 d . . . . . C8 C -0.1114(3) 0.44219(16) -0.36309(12) 0.0158(4) Uani 1 1 d . . . . . H8A H -0.2498 0.4436 -0.3683 0.024 Uiso 1 1 calc R U . . . H8B H -0.0638 0.4409 -0.4176 0.024 Uiso 1 1 calc R U . . . H8C H -0.0642 0.5159 -0.3336 0.024 Uiso 1 1 calc R U . . . B1 B 0.5355(3) 0.31290(18) -0.04509(13) 0.0139(4) Uani 1 1 d . . . . . B2 B 0.9516(3) 0.36019(19) 0.15515(14) 0.0142(4) Uani 1 1 d . . . . . H11 H -0.086(3) 0.3531(19) -0.0654(13) 0.024(6) Uiso 1 1 d . . . . . H12 H 0.076(3) 0.401(2) -0.1043(14) 0.029(6) Uiso 1 1 d . . . . . H13 H 0.093(3) 0.3332(19) -0.0244(14) 0.023(6) Uiso 1 1 d . . . . . H21 H -0.168(3) 0.088(2) -0.3383(14) 0.034(6) Uiso 1 1 d . . . . . H22 H 0.021(3) 0.141(2) -0.3567(15) 0.033(6) Uiso 1 1 d . . . . . H23 H 0.005(3) 0.007(2) -0.3417(13) 0.026(6) 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 F1 0.0173(5) 0.0213(6) 0.0139(6) 0.0004(5) 0.0036(4) -0.0022(4) F2 0.0162(6) 0.0208(5) 0.0173(6) 0.0052(5) -0.0015(5) -0.0016(4) F3 0.0137(5) 0.0187(5) 0.0216(6) -0.0010(5) 0.0011(4) -0.0029(4) F4 0.0233(6) 0.0171(5) 0.0242(7) -0.0025(5) 0.0005(5) 0.0068(5) F5 0.0190(6) 0.0313(6) 0.0188(6) -0.0082(5) 0.0059(5) -0.0023(5) F6 0.0294(7) 0.0245(6) 0.0220(7) 0.0018(5) -0.0104(5) 0.0070(5) F7 0.0220(6) 0.0143(5) 0.0364(8) -0.0003(5) -0.0074(5) -0.0053(5) F8 0.0133(5) 0.0132(5) 0.0227(6) 0.0008(5) 0.0039(4) 0.0020(4) O1 0.0120(6) 0.0130(6) 0.0131(7) -0.0029(5) -0.0002(5) 0.0014(5) O2 0.0160(6) 0.0121(6) 0.0105(7) 0.0024(5) 0.0014(5) 0.0032(5) N1 0.0111(8) 0.0137(8) 0.0115(9) -0.0007(7) -0.0004(7) 0.0019(6) N2 0.0095(8) 0.0110(7) 0.0126(8) -0.0018(7) 0.0000(6) 0.0001(6) C1 0.0049(8) 0.0109(8) 0.0133(9) -0.0005(7) 0.0020(7) -0.0019(6) C2 0.0077(8) 0.0110(8) 0.0130(10) -0.0025(7) 0.0012(7) -0.0006(7) C3 0.0102(8) 0.0155(8) 0.0114(9) 0.0012(8) -0.0007(7) -0.0014(7) C4 0.0112(8) 0.0112(8) 0.0168(10) 0.0034(8) -0.0007(7) 0.0005(7) C5 0.0097(8) 0.0099(8) 0.0168(10) -0.0020(7) 0.0031(7) -0.0007(7) C6 0.0068(8) 0.0127(8) 0.0099(9) -0.0010(7) 0.0002(7) -0.0014(7) C7 0.0093(8) 0.0095(8) 0.0116(9) -0.0021(7) -0.0013(7) -0.0036(7) C8 0.0196(10) 0.0155(9) 0.0122(10) 0.0037(8) -0.0002(8) 0.0031(8) B1 0.0138(10) 0.0143(10) 0.0135(11) 0.0027(9) 0.0006(8) 0.0008(8) B2 0.0125(10) 0.0136(10) 0.0164(11) -0.0009(9) -0.0006(8) 0.0005(8) 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' 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 C7 O2 C8 116.06(13) . . ? C2 N1 H11 111.1(14) . . ? C2 N1 H12 110.2(13) . . ? H11 N1 H12 107.3(19) . . ? C2 N1 H13 111.1(14) . . ? H11 N1 H13 108(2) . . ? H12 N1 H13 109.0(19) . . ? C6 N2 H21 112.1(14) . . ? C6 N2 H22 112.5(14) . . ? H21 N2 H22 108(2) . . ? C6 N2 H23 108.6(14) . . ? H21 N2 H23 107.9(19) . . ? H22 N2 H23 107.4(19) . . ? C6 C1 C2 116.50(15) . . ? C6 C1 C7 124.41(16) . . ? C2 C1 C7 119.08(15) . . ? C3 C2 C1 122.15(16) . . ? C3 C2 N1 118.07(16) . . ? C1 C2 N1 119.72(15) . . ? C2 C3 C4 119.71(17) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.89(16) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.59(16) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 122.14(17) . . ? C5 C6 N2 117.61(15) . . ? C1 C6 N2 120.24(15) . . ? O1 C7 O2 125.49(16) . . ? O1 C7 C1 122.95(16) . . ? O2 C7 C1 111.54(14) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F4 B1 F1 110.48(15) . . ? F4 B1 F3 109.42(15) . . ? F1 B1 F3 109.75(15) . . ? F4 B1 F2 110.94(16) . . ? F1 B1 F2 108.18(15) . . ? F3 B1 F2 108.03(14) . . ? F7 B2 F6 112.14(16) . . ? F7 B2 F8 108.72(15) . . ? F6 B2 F8 110.86(16) . . ? F7 B2 F5 110.51(16) . . ? F6 B2 F5 107.58(15) . . ? F8 B2 F5 106.90(15) . . ? 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 F1 B1 1.397(2) . ? F2 B1 1.409(2) . ? F3 B1 1.404(2) . ? F4 B1 1.379(2) . ? F5 B2 1.416(2) . ? F6 B2 1.377(2) . ? F7 B2 1.375(2) . ? F8 B2 1.406(2) . ? O1 C7 1.205(2) . ? O2 C7 1.328(2) . ? O2 C8 1.455(2) . ? N1 C2 1.466(2) . ? N1 H11 0.85(2) . ? N1 H12 0.95(2) . ? N1 H13 0.89(2) . ? N2 C6 1.469(2) . ? N2 H21 0.95(2) . ? N2 H22 0.92(2) . ? N2 H23 0.92(2) . ? C1 C6 1.397(2) . ? C1 C2 1.400(2) . ? C1 C7 1.502(2) . ? C2 C3 1.377(2) . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8C F6 0.98 2.53 3.443(2) 155.0 3_665 N2 H23 F2 0.92(2) 1.95(2) 2.8699(18) 175(2) 2_544 N2 H23 F3 0.92(2) 2.63(2) 3.1707(19) 118.0(16) 2_544 N1 H13 F1 0.89(2) 2.38(2) 3.063(2) 133.8(18) . N1 H13 F5 0.89(2) 2.04(2) 2.784(2) 140.9(19) 1_455 N2 H22 F1 0.92(2) 2.21(2) 2.8373(19) 125.1(18) 4_565 N2 H22 F7 0.92(2) 2.36(2) 3.1168(19) 139.9(19) 4_565 N2 H22 O2 0.92(2) 2.23(2) 2.7056(19) 111.5(17) . N2 H21 F5 0.95(2) 2.09(2) 2.9937(19) 160(2) 4_465 N2 H21 F6 0.95(2) 2.44(2) 3.1996(19) 136.8(18) 4_465 N1 H12 F5 0.95(2) 2.54(2) 3.1009(19) 117.5(16) 3_665 N1 H12 F8 0.95(2) 1.87(2) 2.8195(19) 173.8(19) 3_665 N1 H11 F3 0.85(2) 1.98(2) 2.8262(19) 169(2) 1_455 N1 H11 F4 0.85(2) 2.61(2) 3.210(2) 128.5(17) 1_455 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 C1 C2 C3 -1.1(2) . . . . ? C7 C1 C2 C3 177.80(15) . . . . ? C6 C1 C2 N1 176.06(15) . . . . ? C7 C1 C2 N1 -5.0(2) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? N1 C2 C3 C4 -177.35(15) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C4 C5 C6 N2 -179.81(15) . . . . ? C2 C1 C6 C5 1.7(2) . . . . ? C7 C1 C6 C5 -177.16(15) . . . . ? C2 C1 C6 N2 -179.54(14) . . . . ? C7 C1 C6 N2 1.6(2) . . . . ? C8 O2 C7 O1 2.2(2) . . . . ? C8 O2 C7 C1 -175.97(14) . . . . ? C6 C1 C7 O1 145.37(17) . . . . ? C2 C1 C7 O1 -33.4(2) . . . . ? C6 C1 C7 O2 -36.4(2) . . . . ? C2 C1 C7 O2 144.77(15) . . . . ?