#------------------------------------------------------------------------------ #$Date: 2023-11-24 01:34:39 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287763 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247782.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_7247782 loop_ _publ_author_name 'Krawczyk, Marta S.' 'Krawczyk, Monika K.' 'Majerz, Irena' _publ_section_title ; Polymorphism of amantadinium niflumate ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00754E _journal_year 2023 _chemical_formula_moiety 'C13 H8 F3 N2 O2, C10 H18 N' _chemical_formula_sum 'C23 H26 F3 N3 O2' _chemical_formula_weight 433.47 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2023-07-03 deposited with the CCDC. 2023-11-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.45(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.276(4) _cell_length_b 6.420(4) _cell_length_c 29.326(9) _cell_measurement_reflns_used 7997 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 67.16 _cell_measurement_theta_min 3.92 _cell_volume 2109.5(16) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.0158 _diffrn_reflns_Laue_measured_fraction_full 0.981 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 13987 _diffrn_reflns_point_group_measured_fraction_full 0.981 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 67.160 _diffrn_reflns_theta_max 67.160 _diffrn_reflns_theta_min 3.945 _exptl_absorpt_coefficient_mu 0.892 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.825 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_description needle _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.035 _exptl_crystal_size_mid 0.018 _exptl_crystal_size_min 0.011 _refine_diff_density_max 0.218 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 3712 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0323 _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^)+(0.0403P)^2^+0.9412P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.0837 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3429 _reflns_number_total 3712 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00754e2.cif _cod_data_source_block II_polymorph _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247782 _shelx_shelxl_version_number 2014/7 _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. ; _shelx_estimated_absorpt_t_min 0.969 _shelx_estimated_absorpt_t_max 0.990 _shelx_res_file ; nifad.res created by SHELXL-2014/7 TITL nifad_a.res in P2(1)/c REM Old TITL NifAd in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.130, Rweak 0.012, Alpha 0.019 REM 0.656 for 365 systematic absences, Orientation as input REM Formula found by SHELXT: C23 N3 O5 CELL 1.54184 11.276 6.420 29.326 90 96.45 90 ZERR 4 0.004 0.004 0.009 0 0.03 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O F UNIT 92 104 12 8 12 temp -173 L.S. 10 PLAN 20 CONF HTAB 2 fmap 2 53 BOND $H EQIV $1 -x, y-1/2, -z+1/2 EQIV $2 -x, y+1/2, -z+1/2 HTAB N1 O2 HTAB C9 N4 HTAB N3 O1 HTAB N3 O1_$1 HTAB N3 O2_$2 ACTA 136 size 0.035 0.018 0.011 WGHT 0.040300 0.941200 FVAR 0.41176 F1 5 0.831978 0.448107 0.490380 11.00000 0.02004 0.05435 = 0.03944 -0.01805 -0.00482 0.00346 F2 5 0.697690 0.496259 0.534443 11.00000 0.04383 0.06514 = 0.01921 -0.01072 0.00641 -0.01742 F3 5 0.720773 0.716655 0.481458 11.00000 0.06092 0.02423 = 0.05029 0.00512 -0.03304 -0.00652 O1 4 0.140866 0.667547 0.265678 11.00000 0.01583 0.01925 = 0.02221 -0.00250 -0.00346 0.00150 O2 4 0.230208 0.378972 0.294692 11.00000 0.02003 0.01810 = 0.02894 0.00425 -0.00410 -0.00382 N1 3 0.434012 0.441103 0.349132 11.00000 0.01959 0.01786 = 0.02128 0.00314 -0.00597 -0.00338 H1N 2 0.372273 0.364519 0.337985 11.00000 -1.20000 C1 1 0.230490 0.569003 0.284489 11.00000 0.01569 0.01817 = 0.01307 -0.00149 0.00125 0.00009 C2 1 0.344373 0.691992 0.294661 11.00000 0.01563 0.01640 = 0.01480 -0.00213 0.00200 0.00016 C3 1 0.442812 0.626027 0.326213 11.00000 0.01710 0.01666 = 0.01515 -0.00198 0.00151 -0.00011 N4 3 0.543968 0.736514 0.333971 11.00000 0.01872 0.02225 = 0.01849 0.00026 -0.00079 -0.00315 C5 1 0.550750 0.915692 0.310967 11.00000 0.01973 0.02261 = 0.01960 -0.00228 0.00239 -0.00674 AFIX 43 H5 2 0.622635 0.993508 0.316278 11.00000 -1.20000 AFIX 0 C6 1 0.460672 0.995136 0.280108 11.00000 0.02292 0.01713 = 0.01794 0.00025 0.00532 -0.00205 AFIX 43 H6 2 0.469674 1.123832 0.264882 11.00000 -1.20000 AFIX 0 C7 1 0.356457 0.879549 0.272211 11.00000 0.01730 0.01815 = 0.01495 -0.00061 0.00212 0.00224 AFIX 43 H7 2 0.292593 0.929509 0.251166 11.00000 -1.20000 AFIX 0 C8 1 0.498704 0.365627 0.389175 11.00000 0.01622 0.02004 = 0.01783 0.00175 0.00147 0.00324 C9 1 0.580971 0.481889 0.417967 11.00000 0.01918 0.01844 = 0.01967 0.00121 0.00083 0.00105 AFIX 43 H9 2 0.601181 0.619688 0.409909 11.00000 -1.20000 AFIX 0 C10 1 0.632860 0.392198 0.458706 11.00000 0.01675 0.02296 = 0.01824 -0.00015 0.00169 0.00311 C11 1 0.608048 0.188885 0.470705 11.00000 0.02115 0.02566 = 0.01739 0.00509 0.00164 0.00428 AFIX 43 H11 2 0.645256 0.129807 0.498390 11.00000 -1.20000 AFIX 0 C12 1 0.527925 0.073772 0.441504 11.00000 0.02130 0.01911 = 0.02323 0.00391 0.00484 0.00110 AFIX 43 H12 2 0.510394 -0.065900 0.449090 11.00000 -1.20000 AFIX 0 C13 1 0.473501 0.160742 0.401508 11.00000 0.01675 0.01971 = 0.02096 -0.00089 0.00168 0.00007 AFIX 43 H13 2 0.418066 0.080529 0.382013 11.00000 -1.20000 AFIX 0 C14 1 0.719329 0.514040 0.490718 11.00000 0.02181 0.02410 = 0.01836 0.00220 -0.00039 0.00377 N3 3 -0.060795 0.559094 0.209626 11.00000 0.01497 0.01502 = 0.01792 -0.00008 -0.00095 0.00075 H3NA 2 0.004276 0.584976 0.230177 11.00000 -1.20000 H3NB 2 -0.097130 0.434787 0.218148 11.00000 -1.20000 H3NC 2 -0.113218 0.668343 0.209983 11.00000 -1.20000 C1A 1 -0.022747 0.534771 0.162493 11.00000 0.01630 0.01550 = 0.01515 -0.00027 -0.00106 0.00055 C2A 1 0.067764 0.357073 0.163119 11.00000 0.01814 0.01733 = 0.01891 0.00142 -0.00084 0.00310 AFIX 23 H2A 2 0.031460 0.226027 0.172695 11.00000 -1.20000 H2B 2 0.138245 0.388614 0.185315 11.00000 -1.20000 AFIX 0 C3A 1 0.106029 0.331968 0.114709 11.00000 0.02362 0.02203 = 0.02177 -0.00016 0.00255 0.00627 AFIX 13 H3A 2 0.165364 0.216207 0.114701 11.00000 -1.20000 AFIX 0 C4A 1 -0.004214 0.281220 0.080869 11.00000 0.03172 0.02150 = 0.01882 -0.00307 0.00235 0.00150 AFIX 23 H4A 2 0.019795 0.261358 0.049710 11.00000 -1.20000 H4B 2 -0.041312 0.150427 0.090170 11.00000 -1.20000 AFIX 0 C5A 1 -0.094289 0.460264 0.080421 11.00000 0.02292 0.02408 = 0.01814 -0.00222 -0.00476 -0.00056 AFIX 13 H5A 2 -0.165727 0.427634 0.058185 11.00000 -1.20000 AFIX 0 C6A 1 -0.132801 0.485442 0.128718 11.00000 0.01622 0.02070 = 0.02112 -0.00064 -0.00277 0.00013 AFIX 23 H6A 2 -0.191715 0.599728 0.128819 11.00000 -1.20000 H6B 2 -0.170690 0.355359 0.137995 11.00000 -1.20000 AFIX 0 C7A 1 0.033887 0.738215 0.148722 11.00000 0.02125 0.01651 = 0.01974 0.00077 -0.00118 -0.00199 AFIX 23 H7A 2 0.104162 0.771757 0.170857 11.00000 -1.20000 H7B 2 -0.024288 0.853570 0.149013 11.00000 -1.20000 AFIX 0 C8A 1 0.072243 0.713612 0.100322 11.00000 0.02614 0.02048 = 0.02040 0.00297 0.00255 -0.00396 AFIX 13 H8A 2 0.109572 0.846010 0.091014 11.00000 -1.20000 AFIX 0 C9A 1 0.162232 0.535259 0.100124 11.00000 0.02113 0.03201 = 0.02129 0.00156 0.00336 0.00025 AFIX 23 H9A 2 0.234136 0.567625 0.121524 11.00000 -1.20000 H9B 2 0.186905 0.519184 0.068965 11.00000 -1.20000 AFIX 0 C10A 1 -0.037668 0.663415 0.066354 11.00000 0.02980 0.02413 = 0.01747 0.00291 -0.00136 0.00351 AFIX 23 H10X 2 -0.096324 0.778250 0.066141 11.00000 -1.20000 H10Y 2 -0.013837 0.649396 0.035021 11.00000 -1.20000 AFIX 0 HKLF 4 REM nifad_a.res in P2(1)/c REM R1 = 0.0323 for 3429 Fo > 4sig(Fo) and 0.0352 for all 3712 data REM 292 parameters refined using 0 restraints END WGHT 0.0385 0.9290 REM Instructions for potential hydrogen bonds HTAB N1 O2 HTAB C9 N4 HTAB N3 O1 HTAB N3 O1_$1 HTAB N3 O2_$2 REM Highest difference peak 0.218, deepest hole -0.241, 1-sigma level 0.039 Q1 1 -0.0775 0.5076 0.1422 11.00000 0.05 0.22 Q2 1 0.0197 0.4440 0.1611 11.00000 0.05 0.21 Q3 1 0.0490 0.7205 0.1200 11.00000 0.05 0.20 Q4 1 0.0177 0.6759 0.0819 11.00000 0.05 0.20 Q5 1 0.6701 0.6295 0.5194 11.00000 0.05 0.20 Q6 1 -0.0465 0.3743 0.0800 11.00000 0.05 0.19 Q7 1 0.0069 0.6389 0.1581 11.00000 0.05 0.19 Q8 1 0.0892 0.3476 0.1402 11.00000 0.05 0.18 Q9 1 0.2903 0.6484 0.2947 11.00000 0.05 0.18 Q10 1 0.0544 0.3086 0.0987 11.00000 0.05 0.18 Q11 1 0.3799 0.6695 0.3112 11.00000 0.05 0.18 Q12 1 0.1113 0.6214 0.0994 11.00000 0.05 0.17 Q13 1 0.6219 0.4260 0.4425 11.00000 0.05 0.17 Q14 1 -0.1154 0.4690 0.0990 11.00000 0.05 0.17 Q15 1 0.3941 0.6392 0.3035 11.00000 0.05 0.17 Q16 1 0.6191 0.2997 0.4628 11.00000 0.05 0.16 Q17 1 0.3395 0.8027 0.2965 11.00000 0.05 0.15 Q18 1 0.8153 0.5844 0.4777 11.00000 0.05 0.15 Q19 1 0.7990 0.4147 0.5219 11.00000 0.05 0.14 Q20 1 0.3580 0.7447 0.2813 11.00000 0.05 0.14 ; _shelx_res_checksum 98511 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.83198(7) 0.44811(15) 0.49038(3) 0.0386(2) Uani 1 1 d . . . . . F2 F 0.69769(8) 0.49626(16) 0.53444(3) 0.0425(2) Uani 1 1 d . . . . . F3 F 0.72077(9) 0.71665(13) 0.48146(3) 0.0481(3) Uani 1 1 d . . . . . O1 O 0.14087(7) 0.66755(13) 0.26568(3) 0.0195(2) Uani 1 1 d . . . . . O2 O 0.23021(8) 0.37897(13) 0.29469(3) 0.0229(2) Uani 1 1 d . . . . . N1 N 0.43401(10) 0.44110(17) 0.34913(4) 0.0202(2) Uani 1 1 d . . . . . H1N H 0.3723(14) 0.365(2) 0.3380(5) 0.024 Uiso 1 1 d . U . . . C1 C 0.23049(10) 0.56900(19) 0.28449(4) 0.0157(2) Uani 1 1 d . . . . . C2 C 0.34437(10) 0.69199(18) 0.29466(4) 0.0156(2) Uani 1 1 d . . . . . C3 C 0.44281(10) 0.62603(19) 0.32621(4) 0.0163(2) Uani 1 1 d . . . . . N4 N 0.54397(9) 0.73651(17) 0.33397(3) 0.0200(2) Uani 1 1 d . . . . . C5 C 0.55075(11) 0.9157(2) 0.31097(4) 0.0206(3) Uani 1 1 d . . . . . H5 H 0.6226 0.9935 0.3163 0.025 Uiso 1 1 calc R U . . . C6 C 0.46067(11) 0.99514(19) 0.28011(4) 0.0191(3) Uani 1 1 d . . . . . H6 H 0.4697 1.1238 0.2649 0.023 Uiso 1 1 calc R U . . . C7 C 0.35646(10) 0.87955(19) 0.27221(4) 0.0168(2) Uani 1 1 d . . . . . H7 H 0.2926 0.9295 0.2512 0.020 Uiso 1 1 calc R U . . . C8 C 0.49870(10) 0.36563(19) 0.38917(4) 0.0181(3) Uani 1 1 d . . . . . C9 C 0.58097(11) 0.48189(19) 0.41797(4) 0.0192(3) Uani 1 1 d . . . . . H9 H 0.6012 0.6197 0.4099 0.023 Uiso 1 1 calc R U . . . C10 C 0.63286(11) 0.3922(2) 0.45871(4) 0.0193(3) Uani 1 1 d . . . . . C11 C 0.60805(11) 0.1889(2) 0.47071(4) 0.0214(3) Uani 1 1 d . . . . . H11 H 0.6453 0.1298 0.4984 0.026 Uiso 1 1 calc R U . . . C12 C 0.52792(11) 0.0738(2) 0.44150(4) 0.0210(3) Uani 1 1 d . . . . . H12 H 0.5104 -0.0659 0.4491 0.025 Uiso 1 1 calc R U . . . C13 C 0.47350(11) 0.1607(2) 0.40151(4) 0.0192(3) Uani 1 1 d . . . . . H13 H 0.4181 0.0805 0.3820 0.023 Uiso 1 1 calc R U . . . C14 C 0.71933(11) 0.5140(2) 0.49072(4) 0.0216(3) Uani 1 1 d . . . . . N3 N -0.06079(9) 0.55909(17) 0.20963(3) 0.0162(2) Uani 1 1 d . . . . . H3NA H 0.0043(14) 0.585(2) 0.2302(5) 0.019 Uiso 1 1 d . U . . . H3NB H -0.0971(13) 0.435(2) 0.2181(5) 0.019 Uiso 1 1 d . U . . . H3NC H -0.1132(13) 0.668(2) 0.2100(5) 0.019 Uiso 1 1 d . U . . . C1A C -0.02275(10) 0.53477(18) 0.16249(4) 0.0159(2) Uani 1 1 d . . . . . C2A C 0.06776(11) 0.35707(19) 0.16312(4) 0.0183(3) Uani 1 1 d . . . . . H2A H 0.0315 0.2260 0.1727 0.022 Uiso 1 1 calc R U . . . H2B H 0.1382 0.3886 0.1853 0.022 Uiso 1 1 calc R U . . . C3A C 0.10603(11) 0.3320(2) 0.11471(4) 0.0225(3) Uani 1 1 d . . . . . H3A H 0.1654 0.2162 0.1147 0.027 Uiso 1 1 calc R U . . . C4A C -0.00421(12) 0.2812(2) 0.08087(4) 0.0241(3) Uani 1 1 d . . . . . H4A H 0.0198 0.2614 0.0497 0.029 Uiso 1 1 calc R U . . . H4B H -0.0413 0.1504 0.0902 0.029 Uiso 1 1 calc R U . . . C5A C -0.09429(11) 0.4603(2) 0.08042(4) 0.0222(3) Uani 1 1 d . . . . . H5A H -0.1657 0.4276 0.0582 0.027 Uiso 1 1 calc R U . . . C6A C -0.13280(11) 0.4854(2) 0.12872(4) 0.0197(3) Uani 1 1 d . . . . . H6A H -0.1917 0.5997 0.1288 0.024 Uiso 1 1 calc R U . . . H6B H -0.1707 0.3554 0.1380 0.024 Uiso 1 1 calc R U . . . C7A C 0.03389(11) 0.73822(19) 0.14872(4) 0.0194(3) Uani 1 1 d . . . . . H7A H 0.1042 0.7718 0.1709 0.023 Uiso 1 1 calc R U . . . H7B H -0.0243 0.8536 0.1490 0.023 Uiso 1 1 calc R U . . . C8A C 0.07224(11) 0.7136(2) 0.10032(4) 0.0223(3) Uani 1 1 d . . . . . H8A H 0.1096 0.8460 0.0910 0.027 Uiso 1 1 calc R U . . . C9A C 0.16223(11) 0.5353(2) 0.10012(5) 0.0247(3) Uani 1 1 d . . . . . H9A H 0.2341 0.5676 0.1215 0.030 Uiso 1 1 calc R U . . . H9B H 0.1869 0.5192 0.0690 0.030 Uiso 1 1 calc R U . . . C10A C -0.03767(12) 0.6634(2) 0.06635(4) 0.0241(3) Uani 1 1 d . . . . . H10X H -0.0963 0.7783 0.0661 0.029 Uiso 1 1 calc R U . . . H10Y H -0.0138 0.6494 0.0350 0.029 Uiso 1 1 calc R U . . . 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 0.0200(4) 0.0543(6) 0.0394(5) -0.0181(4) -0.0048(3) 0.0035(4) F2 0.0438(5) 0.0651(6) 0.0192(4) -0.0107(4) 0.0064(4) -0.0174(5) F3 0.0609(6) 0.0242(4) 0.0503(6) 0.0051(4) -0.0330(5) -0.0065(4) O1 0.0158(4) 0.0193(4) 0.0222(4) -0.0025(4) -0.0035(3) 0.0015(3) O2 0.0200(4) 0.0181(4) 0.0289(5) 0.0043(4) -0.0041(4) -0.0038(4) N1 0.0196(5) 0.0179(5) 0.0213(5) 0.0031(4) -0.0060(4) -0.0034(4) C1 0.0157(6) 0.0182(6) 0.0131(6) -0.0015(5) 0.0013(4) 0.0001(5) C2 0.0156(6) 0.0164(6) 0.0148(6) -0.0021(5) 0.0020(4) 0.0002(5) C3 0.0171(6) 0.0167(6) 0.0152(6) -0.0020(5) 0.0015(4) -0.0001(5) N4 0.0187(5) 0.0222(5) 0.0185(5) 0.0003(4) -0.0008(4) -0.0031(4) C5 0.0197(6) 0.0226(6) 0.0196(6) -0.0023(5) 0.0024(5) -0.0067(5) C6 0.0229(6) 0.0171(6) 0.0179(6) 0.0002(5) 0.0053(5) -0.0020(5) C7 0.0173(6) 0.0182(6) 0.0150(6) -0.0006(5) 0.0021(4) 0.0022(5) C8 0.0162(6) 0.0200(6) 0.0178(6) 0.0017(5) 0.0015(5) 0.0032(5) C9 0.0192(6) 0.0184(6) 0.0197(6) 0.0012(5) 0.0008(5) 0.0011(5) C10 0.0168(6) 0.0230(6) 0.0182(6) -0.0002(5) 0.0017(5) 0.0031(5) C11 0.0212(6) 0.0257(7) 0.0174(6) 0.0051(5) 0.0016(5) 0.0043(5) C12 0.0213(6) 0.0191(6) 0.0232(6) 0.0039(5) 0.0048(5) 0.0011(5) C13 0.0167(6) 0.0197(6) 0.0210(6) -0.0009(5) 0.0017(5) 0.0001(5) C14 0.0218(6) 0.0241(7) 0.0184(6) 0.0022(5) -0.0004(5) 0.0038(5) N3 0.0150(5) 0.0150(5) 0.0179(5) -0.0001(4) -0.0009(4) 0.0007(4) C1A 0.0163(6) 0.0155(6) 0.0152(6) -0.0003(5) -0.0011(4) 0.0006(5) C2A 0.0181(6) 0.0173(6) 0.0189(6) 0.0014(5) -0.0008(5) 0.0031(5) C3A 0.0236(6) 0.0220(6) 0.0218(6) -0.0002(5) 0.0025(5) 0.0063(5) C4A 0.0317(7) 0.0215(6) 0.0188(6) -0.0031(5) 0.0024(5) 0.0015(5) C5A 0.0229(6) 0.0241(7) 0.0181(6) -0.0022(5) -0.0048(5) -0.0006(5) C6A 0.0162(6) 0.0207(6) 0.0211(6) -0.0006(5) -0.0028(5) 0.0001(5) C7A 0.0213(6) 0.0165(6) 0.0197(6) 0.0008(5) -0.0012(5) -0.0020(5) C8A 0.0261(7) 0.0205(6) 0.0204(6) 0.0030(5) 0.0026(5) -0.0040(5) C9A 0.0211(6) 0.0320(7) 0.0213(6) 0.0016(6) 0.0034(5) 0.0002(6) C10A 0.0298(7) 0.0241(7) 0.0175(6) 0.0029(5) -0.0014(5) 0.0035(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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 C3 N1 C8 130.64(11) . . ? C3 N1 H1N 113.4(10) . . ? C8 N1 H1N 115.6(10) . . ? O2 C1 O1 124.49(11) . . ? O2 C1 C2 119.09(10) . . ? O1 C1 C2 116.43(11) . . ? C7 C2 C3 117.05(11) . . ? C7 C2 C1 119.18(11) . . ? C3 C2 C1 123.76(11) . . ? N4 C3 N1 118.76(11) . . ? N4 C3 C2 122.54(11) . . ? N1 C3 C2 118.69(11) . . ? C5 N4 C3 117.66(11) . . ? N4 C5 C6 124.61(11) . . ? N4 C5 H5 117.7 . . ? C6 C5 H5 117.7 . . ? C5 C6 C7 117.33(12) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? C2 C7 C6 120.79(11) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N1 C8 C9 124.79(12) . . ? N1 C8 C13 116.12(11) . . ? C9 C8 C13 119.02(11) . . ? C10 C9 C8 118.89(12) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C11 C10 C9 121.89(12) . . ? C11 C10 C14 117.91(11) . . ? C9 C10 C14 120.19(12) . . ? C12 C11 C10 118.72(12) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 120.42(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 121.04(12) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? F3 C14 F2 106.69(11) . . ? F3 C14 F1 105.92(11) . . ? F2 C14 F1 104.80(10) . . ? F3 C14 C10 113.92(11) . . ? F2 C14 C10 112.39(11) . . ? F1 C14 C10 112.44(11) . . ? C1A N3 H3NA 109.6(9) . . ? C1A N3 H3NB 109.5(9) . . ? H3NA N3 H3NB 108.7(12) . . ? C1A N3 H3NC 109.9(9) . . ? H3NA N3 H3NC 109.0(13) . . ? H3NB N3 H3NC 110.1(12) . . ? N3 C1A C7A 109.01(10) . . ? N3 C1A C2A 109.02(10) . . ? C7A C1A C2A 110.04(11) . . ? N3 C1A C6A 108.81(10) . . ? C7A C1A C6A 109.77(10) . . ? C2A C1A C6A 110.16(10) . . ? C1A C2A C3A 108.85(10) . . ? C1A C2A H2A 109.9 . . ? C3A C2A H2A 109.9 . . ? C1A C2A H2B 109.9 . . ? C3A C2A H2B 109.9 . . ? H2A C2A H2B 108.3 . . ? C9A C3A C4A 109.29(11) . . ? C9A C3A C2A 109.64(11) . . ? C4A C3A C2A 109.15(11) . . ? C9A C3A H3A 109.6 . . ? C4A C3A H3A 109.6 . . ? C2A C3A H3A 109.6 . . ? C5A C4A C3A 109.50(11) . . ? C5A C4A H4A 109.8 . . ? C3A C4A H4A 109.8 . . ? C5A C4A H4B 109.8 . . ? C3A C4A H4B 109.8 . . ? H4A C4A H4B 108.2 . . ? C10A C5A C4A 110.22(11) . . ? C10A C5A C6A 109.20(11) . . ? C4A C5A C6A 109.07(10) . . ? C10A C5A H5A 109.4 . . ? C4A C5A H5A 109.4 . . ? C6A C5A H5A 109.4 . . ? C1A C6A C5A 109.01(10) . . ? C1A C6A H6A 109.9 . . ? C5A C6A H6A 109.9 . . ? C1A C6A H6B 109.9 . . ? C5A C6A H6B 109.9 . . ? H6A C6A H6B 108.3 . . ? C1A C7A C8A 108.99(10) . . ? C1A C7A H7A 109.9 . . ? C8A C7A H7A 109.9 . . ? C1A C7A H7B 109.9 . . ? C8A C7A H7B 109.9 . . ? H7A C7A H7B 108.3 . . ? C9A C8A C10A 109.14(11) . . ? C9A C8A C7A 109.62(10) . . ? C10A C8A C7A 109.29(11) . . ? C9A C8A H8A 109.6 . . ? C10A C8A H8A 109.6 . . ? C7A C8A H8A 109.6 . . ? C8A C9A C3A 109.93(11) . . ? C8A C9A H9A 109.7 . . ? C3A C9A H9A 109.7 . . ? C8A C9A H9B 109.7 . . ? C3A C9A H9B 109.7 . . ? H9A C9A H9B 108.2 . . ? C5A C10A C8A 109.59(10) . . ? C5A C10A H10X 109.8 . . ? C8A C10A H10X 109.8 . . ? C5A C10A H10Y 109.8 . . ? C8A C10A H10Y 109.8 . . ? H10X C10A H10Y 108.2 . . ? 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 C14 1.3400(16) . ? F2 C14 1.3368(16) . ? F3 C14 1.3293(18) . ? O1 C1 1.2652(15) . ? O2 C1 1.2562(17) . ? N1 C3 1.3733(17) . ? N1 C8 1.3976(17) . ? N1 H1N 0.884(16) . ? C1 C2 1.5084(17) . ? C2 C7 1.3864(18) . ? C2 C3 1.4272(17) . ? C3 N4 1.3408(16) . ? N4 C5 1.3401(18) . ? C5 C6 1.3800(18) . ? C5 H5 0.9500 . ? C6 C7 1.3871(18) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.3981(18) . ? C8 C13 1.4017(19) . ? C9 C10 1.3944(18) . ? C9 H9 0.9500 . ? C10 C11 1.389(2) . ? C10 C14 1.4961(18) . ? C11 C12 1.3863(19) . ? C11 H11 0.9500 . ? C12 C13 1.3793(18) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? N3 C1A 1.5007(16) . ? N3 H3NA 0.911(16) . ? N3 H3NB 0.944(16) . ? N3 H3NC 0.918(16) . ? C1A C7A 1.5280(18) . ? C1A C2A 1.5295(17) . ? C1A C6A 1.5314(17) . ? C2A C3A 1.5379(18) . ? C2A H2A 0.9900 . ? C2A H2B 0.9900 . ? C3A C9A 1.533(2) . ? C3A C4A 1.5359(19) . ? C3A H3A 1.0000 . ? C4A C5A 1.5330(19) . ? C4A H4A 0.9900 . ? C4A H4B 0.9900 . ? C5A C10A 1.529(2) . ? C5A C6A 1.5359(18) . ? C5A H5A 1.0000 . ? C6A H6A 0.9900 . ? C6A H6B 0.9900 . ? C7A C8A 1.5377(18) . ? C7A H7A 0.9900 . ? C7A H7B 0.9900 . ? C8A C9A 1.5304(19) . ? C8A C10A 1.5345(19) . ? C8A H8A 1.0000 . ? C9A H9A 0.9900 . ? C9A H9B 0.9900 . ? C10A H10X 0.9900 . ? C10A H10Y 0.9900 . ? 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 N1 H1N O2 0.884(16) 1.931(16) 2.6767(17) 141.0(14) . C9 H9 N4 0.95 2.37 2.9467(18) 118.7 . N3 H3NA O1 0.911(16) 1.838(16) 2.7419(16) 171.5(14) . N3 H3NB O1 0.944(16) 1.861(16) 2.794(2) 169.3(13) 2_545 N3 H3NC O2 0.918(16) 1.883(16) 2.7979(17) 173.9(13) 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 O2 C1 C2 C7 161.27(11) . . . . ? O1 C1 C2 C7 -18.35(16) . . . . ? O2 C1 C2 C3 -18.21(17) . . . . ? O1 C1 C2 C3 162.17(11) . . . . ? C8 N1 C3 N4 19.69(19) . . . . ? C8 N1 C3 C2 -161.01(12) . . . . ? C7 C2 C3 N4 -0.80(17) . . . . ? C1 C2 C3 N4 178.69(11) . . . . ? C7 C2 C3 N1 179.93(11) . . . . ? C1 C2 C3 N1 -0.58(17) . . . . ? N1 C3 N4 C5 179.55(11) . . . . ? C2 C3 N4 C5 0.27(17) . . . . ? C3 N4 C5 C6 0.47(18) . . . . ? N4 C5 C6 C7 -0.62(19) . . . . ? C3 C2 C7 C6 0.62(17) . . . . ? C1 C2 C7 C6 -178.89(11) . . . . ? C5 C6 C7 C2 0.03(18) . . . . ? C3 N1 C8 C9 8.0(2) . . . . ? C3 N1 C8 C13 -174.90(12) . . . . ? N1 C8 C9 C10 175.27(11) . . . . ? C13 C8 C9 C10 -1.78(18) . . . . ? C8 C9 C10 C11 2.11(18) . . . . ? C8 C9 C10 C14 -178.75(11) . . . . ? C9 C10 C11 C12 -0.99(18) . . . . ? C14 C10 C11 C12 179.86(11) . . . . ? C10 C11 C12 C13 -0.46(18) . . . . ? C11 C12 C13 C8 0.75(19) . . . . ? N1 C8 C13 C12 -176.90(11) . . . . ? C9 C8 C13 C12 0.39(18) . . . . ? C11 C10 C14 F3 -167.72(12) . . . . ? C9 C10 C14 F3 13.11(17) . . . . ? C11 C10 C14 F2 -46.21(15) . . . . ? C9 C10 C14 F2 134.62(12) . . . . ? C11 C10 C14 F1 71.76(15) . . . . ? C9 C10 C14 F1 -107.41(14) . . . . ? N3 C1A C2A C3A 179.72(10) . . . . ? C7A C1A C2A C3A -60.78(13) . . . . ? C6A C1A C2A C3A 60.38(13) . . . . ? C1A C2A C3A C9A 59.61(13) . . . . ? C1A C2A C3A C4A -60.07(13) . . . . ? C9A C3A C4A C5A -59.10(14) . . . . ? C2A C3A C4A C5A 60.79(14) . . . . ? C3A C4A C5A C10A 59.11(14) . . . . ? C3A C4A C5A C6A -60.77(14) . . . . ? N3 C1A C6A C5A -179.96(10) . . . . ? C7A C1A C6A C5A 60.82(13) . . . . ? C2A C1A C6A C5A -60.50(13) . . . . ? C10A C5A C6A C1A -60.36(13) . . . . ? C4A C5A C6A C1A 60.14(13) . . . . ? N3 C1A C7A C8A -179.70(9) . . . . ? C2A C1A C7A C8A 60.79(13) . . . . ? C6A C1A C7A C8A -60.60(13) . . . . ? C1A C7A C8A C9A -59.59(13) . . . . ? C1A C7A C8A C10A 59.98(13) . . . . ? C10A C8A C9A C3A -60.41(14) . . . . ? C7A C8A C9A C3A 59.26(14) . . . . ? C4A C3A C9A C8A 60.25(14) . . . . ? C2A C3A C9A C8A -59.35(13) . . . . ? C4A C5A C10A C8A -59.41(14) . . . . ? C6A C5A C10A C8A 60.39(14) . . . . ? C9A C8A C10A C5A 59.63(14) . . . . ? C7A C8A C10A C5A -60.24(14) . . . . ?