#------------------------------------------------------------------------------ #$Date: 2023-11-24 01:34:39 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287763 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247783.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_7247783 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 108.29(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.953(6) _cell_length_b 6.359(3) _cell_length_c 20.573(6) _cell_measurement_reflns_used 8748 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 73.24 _cell_measurement_theta_min 2.71 _cell_volume 2105.8(14) _computing_cell_refinement 'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix-Arc 150' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 16441 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 68.000 _diffrn_reflns_theta_max 73.031 _diffrn_reflns_theta_min 2.745 _exptl_absorpt_coefficient_mu 0.894 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.551 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.367 _exptl_crystal_description needle _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.377 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 328 _refine_ls_number_reflns 4076 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0443 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+0.8293P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1178 _refine_ls_wR_factor_ref 0.1222 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3577 _reflns_number_total 4076 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00754e2.cif _cod_data_source_block I_polymorph _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247783 _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 0.763 _shelx_estimated_absorpt_t_max 0.965 _shelx_res_file ; nifadd2.res created by SHELXL-2014/7 TITL nifadd_auto_a.res in P2(1)/c REM Old TITL NiFAdD_auto in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.246, Rweak 0.020, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C26 N12 N32 CELL 1.54184 16.953 6.359 20.573 90 108.29 90 ZERR 4 0.006 0.003 0.006 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 L.S. 10 TEMP -173 CONF BOND $H htab 2 EQIV $1 -x+1, y-1/2, -z+1/2 EQIV $2 x, y-1, z HTAB N1 O2 HTAB C9 N4 HTAB N3 O1_$1 HTAB N3 O1_$2 HTAB N3 O2 fmap 2 ACTA 136 SIZE 0.04 0.06 0.32 WGHT 0.071500 0.829300 FVAR 3.69657 O1 4 0.483885 0.908778 0.330363 11.00000 0.02245 0.02308 = 0.01650 0.00131 0.00389 0.00173 O2 4 0.543420 0.610338 0.377957 11.00000 0.02544 0.02054 = 0.02290 -0.00224 0.00201 0.00050 C1 1 0.532249 0.807051 0.379604 11.00000 0.01802 0.02191 = 0.01737 0.00045 0.00771 -0.00068 C2 1 0.580512 0.926456 0.442596 11.00000 0.01941 0.02101 = 0.01546 0.00091 0.00653 -0.00227 C3 1 0.656701 0.852590 0.489368 11.00000 0.02019 0.02171 = 0.01703 0.00112 0.00723 -0.00240 N4 3 0.698808 0.961280 0.545401 11.00000 0.02422 0.02537 = 0.01732 -0.00255 0.00587 -0.00146 C5 1 0.667387 1.145947 0.556887 11.00000 0.02628 0.02742 = 0.01759 -0.00452 0.00745 -0.00295 AFIX 43 H5 2 0.697373 1.222598 0.596588 11.00000 -1.20000 AFIX 0 C6 1 0.594382 1.232356 0.514928 11.00000 0.02804 0.02227 = 0.02135 -0.00222 0.01210 -0.00064 AFIX 43 H6 2 0.574496 1.363753 0.525301 11.00000 -1.20000 AFIX 0 C7 1 0.551250 1.119004 0.456905 11.00000 0.02068 0.02355 = 0.01758 0.00221 0.00777 -0.00007 AFIX 43 H7 2 0.501045 1.174147 0.426634 11.00000 -1.20000 AFIX 0 N1 3 0.688659 0.663821 0.476755 11.00000 0.02089 0.02207 = 0.02036 -0.00200 0.00194 0.00064 H1N 2 0.653471 0.590105 0.443927 11.00000 -1.20000 C8 1 0.769176 0.581917 0.502590 11.00000 0.02093 0.02517 = 0.01774 0.00339 0.00746 0.00082 C9 1 0.836187 0.687067 0.547976 11.00000 0.02380 0.02497 = 0.02485 0.00066 0.00749 0.00025 AFIX 43 H9 2 0.829041 0.822583 0.564744 11.00000 -1.20000 AFIX 0 C10 1 0.913783 0.590139 0.568328 11.00000 0.02094 0.03486 = 0.03139 -0.00075 0.00603 0.00082 C11 1 0.926557 0.392462 0.545374 11.00000 0.02230 0.03470 = 0.04052 -0.00013 0.00879 0.00643 AFIX 43 H11 2 0.979998 0.329147 0.560188 11.00000 -1.20000 AFIX 0 C12 1 0.859512 0.288692 0.500201 11.00000 0.02984 0.02834 = 0.03671 -0.00152 0.01406 0.00305 AFIX 43 H12 2 0.866918 0.152791 0.483834 11.00000 -1.20000 AFIX 0 C13 1 0.782058 0.382327 0.478958 11.00000 0.02486 0.02505 = 0.02380 -0.00060 0.00874 -0.00086 AFIX 43 H13 2 0.736776 0.310087 0.447793 11.00000 -1.20000 AFIX 0 part 1 C14 1 0.981020 0.723256 0.609195 10.50000 0.03320 0.04394 = 0.04230 -0.00940 0.00288 0.01668 F1 5 0.968329 0.807575 0.662872 10.50000 0.02594 0.08115 = 0.04146 -0.03897 0.00645 -0.00623 F2 5 1.049816 0.619158 0.634387 10.50000 0.03048 0.15331 = 0.15266 -0.09198 -0.01883 0.01396 F3 5 1.003025 0.881193 0.577855 10.50000 0.03469 0.04435 = 0.06913 -0.01296 0.01604 -0.02118 same 0.005 C14 > F3 same 0.005 C141 > F31 part 2 C141 1 0.986598 0.694896 0.622698 10.50000 0.00798 0.04169 = 0.05268 -0.00279 -0.00922 0.00342 F11 5 0.981550 0.677353 0.684300 10.50000 0.09990 0.33496 = 0.05305 -0.08658 0.03586 -0.11717 F21 5 1.059090 0.616765 0.627772 10.50000 0.01062 0.05125 = 0.05317 -0.00987 0.00025 0.00963 F31 5 0.986534 0.896669 0.610512 10.50000 0.09432 0.04178 = 0.37957 -0.01539 -0.13154 -0.00156 part 0 N3 3 0.453111 0.322034 0.282119 11.00000 0.01964 0.02046 = 0.01610 -0.00054 0.00468 0.00024 H3NA 2 0.472977 0.330155 0.244081 11.00000 -1.50000 H3NB 2 0.468614 0.183673 0.304655 11.00000 -1.50000 H3NC 2 0.480651 0.429435 0.314314 11.00000 -1.50000 C1A 1 0.360036 0.354079 0.259764 11.00000 0.01785 0.02007 = 0.01781 0.00025 0.00509 0.00086 C2A 1 0.317168 0.157605 0.222370 11.00000 0.02104 0.02022 = 0.02610 -0.00392 0.00537 0.00142 AFIX 23 H2A 2 0.332653 0.033792 0.252913 11.00000 -1.20000 H2B 2 0.334824 0.131561 0.181549 11.00000 -1.20000 AFIX 0 C3A 1 0.222435 0.191850 0.200568 11.00000 0.02087 0.02365 = 0.03647 -0.00864 0.00372 0.00009 AFIX 13 H3A 2 0.193511 0.064397 0.175808 11.00000 -1.20000 AFIX 0 C4A 1 0.195933 0.229281 0.264459 11.00000 0.02306 0.02364 = 0.04312 0.00048 0.01289 -0.00082 AFIX 23 H4A 2 0.134992 0.249085 0.250874 11.00000 -1.20000 H4B 2 0.210615 0.105389 0.295037 11.00000 -1.20000 AFIX 0 C5A 1 0.239834 0.424864 0.302339 11.00000 0.02441 0.02577 = 0.02497 0.00202 0.01179 0.00228 AFIX 13 H5A 2 0.222439 0.449179 0.343895 11.00000 -1.20000 AFIX 0 C6A 1 0.334455 0.390565 0.324027 11.00000 0.02479 0.02366 = 0.01734 0.00121 0.00766 0.00142 AFIX 23 H6A 2 0.363549 0.515463 0.349075 11.00000 -1.20000 H6B 2 0.349946 0.267186 0.354761 11.00000 -1.20000 AFIX 0 C7A 1 0.337631 0.546203 0.213107 11.00000 0.02402 0.02194 = 0.01825 0.00178 0.00802 0.00215 AFIX 23 H7A 2 0.355537 0.524394 0.172197 11.00000 -1.20000 H7B 2 0.366432 0.672085 0.237699 11.00000 -1.20000 AFIX 0 C8A 1 0.242980 0.579373 0.191233 11.00000 0.02433 0.02503 = 0.02000 0.00250 0.00570 0.00675 AFIX 13 H8A 2 0.227563 0.704351 0.160322 11.00000 -1.20000 AFIX 0 C9A 1 0.199492 0.382839 0.153226 11.00000 0.02311 0.03592 = 0.02397 -0.00751 0.00159 0.00634 AFIX 23 H9A 2 0.138549 0.403696 0.138173 11.00000 -1.20000 H9B 2 0.216740 0.358819 0.112097 11.00000 -1.20000 AFIX 0 C10A 1 0.216656 0.616260 0.255112 11.00000 0.02334 0.02331 = 0.02474 -0.00058 0.00835 0.00378 AFIX 23 H10A 2 0.244798 0.742986 0.279610 11.00000 -1.20000 H10B 2 0.155927 0.639930 0.241505 11.00000 -1.20000 AFIX 0 HKLF 4 REM nifadd_auto_a.res in P2(1)/c REM R1 = 0.0443 for 3577 Fo > 4sig(Fo) and 0.0501 for all 4076 data REM 328 parameters refined using 6 restraints END WGHT 0.0686 0.6474 REM Instructions for potential hydrogen bonds HTAB N1 O2 HTAB C9 N4 HTAB N3 O1_$1 HTAB N3 O1_$2 HTAB N3 O2 REM Highest difference peak 0.377, deepest hole -0.334, 1-sigma level 0.051 Q1 1 1.0401 0.7666 0.6017 11.00000 0.05 0.38 Q2 1 1.0193 0.5639 0.6835 11.00000 0.05 0.27 Q3 1 0.3479 0.3742 0.2903 11.00000 0.05 0.23 Q4 1 0.8741 0.6242 0.5607 11.00000 0.05 0.22 Q5 1 0.2887 0.5301 0.2029 11.00000 0.05 0.21 Q6 1 0.2824 0.4213 0.3094 11.00000 0.05 0.19 Q7 1 0.2681 0.1769 0.2109 11.00000 0.05 0.19 Q8 1 0.3385 0.2605 0.2412 11.00000 0.05 0.18 Q9 1 0.8100 0.6549 0.5143 11.00000 0.05 0.18 Q10 1 0.2164 0.3385 0.2809 11.00000 0.05 0.17 Q11 1 0.9307 0.6200 0.5893 11.00000 0.05 0.16 Q12 1 0.4075 0.3262 0.2690 11.00000 0.05 0.15 Q13 1 0.5611 1.1370 0.4999 11.00000 0.05 0.15 Q14 1 0.6340 1.2056 0.5200 11.00000 0.05 0.15 Q15 1 0.2330 0.5849 0.2185 11.00000 0.05 0.15 Q16 1 0.5473 0.3506 0.3206 11.00000 0.05 0.14 Q17 1 0.5435 0.8281 0.4232 11.00000 0.05 0.14 Q18 1 0.7481 0.9664 0.5504 11.00000 0.05 0.14 Q19 1 0.6924 0.9424 0.5091 11.00000 0.05 0.14 Q20 1 0.5950 0.5268 0.3821 11.00000 0.05 0.14 ; _shelx_res_checksum 26788 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 O1 O 0.48389(6) 0.90878(16) 0.33036(5) 0.0212(2) Uani 1 1 d . . . . . O2 O 0.54342(6) 0.61034(16) 0.37796(5) 0.0243(2) Uani 1 1 d . . . . . C1 C 0.53225(8) 0.8071(2) 0.37960(7) 0.0186(3) Uani 1 1 d . . . . . C2 C 0.58051(8) 0.9265(2) 0.44260(6) 0.0184(3) Uani 1 1 d . . . . . C3 C 0.65670(8) 0.8526(2) 0.48937(7) 0.0193(3) Uani 1 1 d . . . . . N4 N 0.69881(7) 0.9613(2) 0.54540(6) 0.0225(3) Uani 1 1 d . . . . . C5 C 0.66739(9) 1.1459(2) 0.55689(7) 0.0236(3) Uani 1 1 d . . . . . H5 H 0.6974 1.2226 0.5966 0.028 Uiso 1 1 calc R U . . . C6 C 0.59438(9) 1.2324(2) 0.51493(7) 0.0229(3) Uani 1 1 d . . . . . H6 H 0.5745 1.3638 0.5253 0.027 Uiso 1 1 calc R U . . . C7 C 0.55125(8) 1.1190(2) 0.45690(7) 0.0202(3) Uani 1 1 d . . . . . H7 H 0.5010 1.1741 0.4266 0.024 Uiso 1 1 calc R U . . . N1 N 0.68866(7) 0.6638(2) 0.47676(6) 0.0222(3) Uani 1 1 d . . . . . H1N H 0.6535(10) 0.590(3) 0.4439(9) 0.027 Uiso 1 1 d . U . . . C8 C 0.76918(8) 0.5819(2) 0.50259(7) 0.0210(3) Uani 1 1 d . . . . . C9 C 0.83619(8) 0.6871(2) 0.54798(7) 0.0246(3) Uani 1 1 d . . . . . H9 H 0.8290 0.8226 0.5647 0.029 Uiso 1 1 calc R U . . . C10 C 0.91378(9) 0.5901(3) 0.56833(8) 0.0296(4) Uani 1 1 d . . . . . C11 C 0.92656(9) 0.3925(3) 0.54537(9) 0.0328(4) Uani 1 1 d . . . . . H11 H 0.9800 0.3291 0.5602 0.039 Uiso 1 1 calc R U . . . C12 C 0.85951(9) 0.2887(3) 0.50020(8) 0.0308(4) Uani 1 1 d . . . . . H12 H 0.8669 0.1528 0.4838 0.037 Uiso 1 1 calc R U . . . C13 C 0.78206(9) 0.3823(2) 0.47896(7) 0.0243(3) Uani 1 1 d . . . . . H13 H 0.7368 0.3101 0.4478 0.029 Uiso 1 1 calc R U . . . C14 C 0.9810(4) 0.7233(8) 0.6092(3) 0.042(2) Uani 0.5 1 d D . P A 1 F1 F 0.96833(19) 0.8076(6) 0.66287(17) 0.0505(9) Uani 0.5 1 d D . P A 1 F2 F 1.0498(4) 0.6192(11) 0.6344(4) 0.123(3) Uani 0.5 1 d D . P A 1 F3 F 1.0030(2) 0.8812(6) 0.5779(2) 0.0494(8) Uani 0.5 1 d D . P A 1 C141 C 0.9866(3) 0.6949(10) 0.6227(3) 0.038(2) Uani 0.5 1 d D . P A 2 F11 F 0.9815(3) 0.6774(14) 0.6843(2) 0.160(4) Uani 0.5 1 d D . P A 2 F21 F 1.0591(3) 0.6168(7) 0.6278(2) 0.0406(9) Uani 0.5 1 d D . P A 2 F31 F 0.9865(4) 0.8967(8) 0.6105(5) 0.220(6) Uani 0.5 1 d D . P A 2 N3 N 0.45311(7) 0.3220(2) 0.28212(6) 0.0189(3) Uani 1 1 d . . . . . H3NA H 0.4730(10) 0.330(3) 0.2441(9) 0.028 Uiso 1 1 d . U . . . H3NB H 0.4686(10) 0.184(3) 0.3047(9) 0.028 Uiso 1 1 d . U . . . H3NC H 0.4807(10) 0.429(3) 0.3143(9) 0.028 Uiso 1 1 d . U . . . C1A C 0.36004(8) 0.3541(2) 0.25976(7) 0.0187(3) Uani 1 1 d . . . . . C2A C 0.31717(8) 0.1576(2) 0.22237(7) 0.0229(3) Uani 1 1 d . . . . . H2A H 0.3327 0.0338 0.2529 0.028 Uiso 1 1 calc R U . . . H2B H 0.3348 0.1316 0.1815 0.028 Uiso 1 1 calc R U . . . C3A C 0.22244(9) 0.1918(3) 0.20057(8) 0.0282(3) Uani 1 1 d . . . . . H3A H 0.1935 0.0644 0.1758 0.034 Uiso 1 1 calc R U . . . C4A C 0.19593(9) 0.2293(3) 0.26446(9) 0.0294(3) Uani 1 1 d . . . . . H4A H 0.1350 0.2491 0.2509 0.035 Uiso 1 1 calc R U . . . H4B H 0.2106 0.1054 0.2950 0.035 Uiso 1 1 calc R U . . . C5A C 0.23983(9) 0.4249(2) 0.30234(7) 0.0241(3) Uani 1 1 d . . . . . H5A H 0.2224 0.4492 0.3439 0.029 Uiso 1 1 calc R U . . . C6A C 0.33445(8) 0.3906(2) 0.32403(7) 0.0217(3) Uani 1 1 d . . . . . H6A H 0.3635 0.5155 0.3491 0.026 Uiso 1 1 calc R U . . . H6B H 0.3499 0.2672 0.3548 0.026 Uiso 1 1 calc R U . . . C7A C 0.33763(8) 0.5462(2) 0.21311(7) 0.0211(3) Uani 1 1 d . . . . . H7A H 0.3555 0.5244 0.1722 0.025 Uiso 1 1 calc R U . . . H7B H 0.3664 0.6721 0.2377 0.025 Uiso 1 1 calc R U . . . C8A C 0.24298(9) 0.5794(2) 0.19123(7) 0.0234(3) Uani 1 1 d . . . . . H8A H 0.2276 0.7044 0.1603 0.028 Uiso 1 1 calc R U . . . C9A C 0.19949(9) 0.3828(3) 0.15323(8) 0.0290(4) Uani 1 1 d . . . . . H9A H 0.1385 0.4037 0.1382 0.035 Uiso 1 1 calc R U . . . H9B H 0.2167 0.3588 0.1121 0.035 Uiso 1 1 calc R U . . . C10A C 0.21666(9) 0.6163(2) 0.25511(7) 0.0236(3) Uani 1 1 d . . . . . H10A H 0.2448 0.7430 0.2796 0.028 Uiso 1 1 calc R U . . . H10B H 0.1559 0.6399 0.2415 0.028 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 O1 0.0224(5) 0.0231(5) 0.0165(5) 0.0013(4) 0.0039(4) 0.0017(4) O2 0.0254(5) 0.0205(5) 0.0229(5) -0.0022(4) 0.0020(4) 0.0005(4) C1 0.0180(6) 0.0219(7) 0.0174(6) 0.0004(5) 0.0077(5) -0.0007(5) C2 0.0194(6) 0.0210(7) 0.0155(6) 0.0009(5) 0.0065(5) -0.0023(5) C3 0.0202(6) 0.0217(7) 0.0170(6) 0.0011(5) 0.0072(5) -0.0024(5) N4 0.0242(6) 0.0254(7) 0.0173(5) -0.0025(5) 0.0059(4) -0.0015(5) C5 0.0263(7) 0.0274(8) 0.0176(6) -0.0045(6) 0.0075(5) -0.0030(6) C6 0.0280(7) 0.0223(7) 0.0214(7) -0.0022(6) 0.0121(6) -0.0006(6) C7 0.0207(6) 0.0235(7) 0.0176(6) 0.0022(5) 0.0078(5) -0.0001(5) N1 0.0209(6) 0.0221(6) 0.0204(6) -0.0020(5) 0.0019(5) 0.0006(5) C8 0.0209(7) 0.0252(7) 0.0177(6) 0.0034(5) 0.0075(5) 0.0008(5) C9 0.0238(7) 0.0250(8) 0.0249(7) 0.0007(6) 0.0075(6) 0.0002(6) C10 0.0209(7) 0.0349(9) 0.0314(8) -0.0007(7) 0.0060(6) 0.0008(6) C11 0.0223(7) 0.0347(10) 0.0405(9) -0.0001(7) 0.0088(6) 0.0064(6) C12 0.0298(8) 0.0283(8) 0.0367(8) -0.0015(7) 0.0141(7) 0.0030(6) C13 0.0249(7) 0.0251(8) 0.0238(7) -0.0006(6) 0.0087(6) -0.0009(6) C14 0.033(4) 0.044(4) 0.042(3) -0.009(2) 0.003(2) 0.017(2) F1 0.0259(11) 0.081(3) 0.0415(19) -0.0390(16) 0.0064(12) -0.0062(16) F2 0.030(3) 0.153(6) 0.153(6) -0.092(4) -0.019(3) 0.014(3) F3 0.0347(13) 0.0444(19) 0.0691(16) -0.0130(13) 0.0160(12) -0.0212(12) C141 0.008(2) 0.042(3) 0.053(3) -0.003(3) -0.0092(18) 0.003(2) F11 0.100(4) 0.335(10) 0.053(3) -0.087(4) 0.036(3) -0.117(5) F21 0.0106(15) 0.051(2) 0.0532(18) -0.0099(15) 0.0003(13) 0.0096(12) F31 0.094(5) 0.042(3) 0.380(14) -0.015(6) -0.132(7) -0.002(3) N3 0.0196(6) 0.0205(6) 0.0161(5) -0.0005(5) 0.0047(4) 0.0002(5) C1A 0.0179(6) 0.0201(7) 0.0178(6) 0.0002(5) 0.0051(5) 0.0009(5) C2A 0.0210(7) 0.0202(7) 0.0261(7) -0.0039(6) 0.0054(5) 0.0014(6) C3A 0.0209(7) 0.0237(8) 0.0365(8) -0.0086(6) 0.0037(6) 0.0001(6) C4A 0.0231(7) 0.0236(8) 0.0431(9) 0.0005(7) 0.0129(6) -0.0008(6) C5A 0.0244(7) 0.0258(8) 0.0250(7) 0.0020(6) 0.0118(6) 0.0023(6) C6A 0.0248(7) 0.0237(7) 0.0173(6) 0.0012(5) 0.0077(5) 0.0014(6) C7A 0.0240(7) 0.0219(7) 0.0183(6) 0.0018(5) 0.0080(5) 0.0021(6) C8A 0.0243(7) 0.0250(8) 0.0200(7) 0.0025(6) 0.0057(5) 0.0068(6) C9A 0.0231(7) 0.0359(9) 0.0240(7) -0.0075(6) 0.0016(6) 0.0063(6) C10A 0.0233(7) 0.0233(8) 0.0247(7) -0.0006(6) 0.0084(6) 0.0038(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 O1 C1 O2 123.29(13) . . ? O1 C1 C2 118.25(13) . . ? O2 C1 C2 118.43(12) . . ? C7 C2 C3 117.13(13) . . ? C7 C2 C1 119.65(12) . . ? C3 C2 C1 123.22(13) . . ? N4 C3 N1 118.50(13) . . ? N4 C3 C2 122.34(13) . . ? N1 C3 C2 119.16(12) . . ? C5 N4 C3 117.97(12) . . ? N4 C5 C6 124.46(13) . . ? N4 C5 H5 117.8 . . ? C6 C5 H5 117.8 . . ? C5 C6 C7 117.20(14) . . ? C5 C6 H6 121.4 . . ? C7 C6 H6 121.4 . . ? C2 C7 C6 120.89(13) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C3 N1 C8 130.39(13) . . ? C3 N1 H1N 113.4(11) . . ? C8 N1 H1N 115.9(11) . . ? C9 C8 C13 118.95(13) . . ? C9 C8 N1 124.62(14) . . ? C13 C8 N1 116.41(13) . . ? C10 C9 C8 118.90(15) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C11 C10 C9 122.25(15) . . ? C11 C10 C14 123.2(2) . . ? C9 C10 C14 114.2(2) . . ? C11 C10 C141 117.9(3) . . ? C9 C10 C141 119.7(3) . . ? C10 C11 C12 118.51(15) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 120.26(16) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 121.13(14) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? F2 C14 F1 103.7(6) . . ? F2 C14 F3 103.2(5) . . ? F1 C14 F3 104.5(4) . . ? F2 C14 C10 112.1(5) . . ? F1 C14 C10 114.9(4) . . ? F3 C14 C10 117.0(5) . . ? F21 C141 F11 103.8(5) . . ? F21 C141 F31 109.5(5) . . ? F11 C141 F31 105.9(5) . . ? F21 C141 C10 114.7(4) . . ? F11 C141 C10 112.9(4) . . ? F31 C141 C10 109.5(5) . . ? C1A N3 H3NA 110.5(10) . . ? C1A N3 H3NB 111.1(10) . . ? H3NA N3 H3NB 108.9(14) . . ? C1A N3 H3NC 110.3(10) . . ? H3NA N3 H3NC 108.0(15) . . ? H3NB N3 H3NC 107.9(14) . . ? N3 C1A C7A 109.21(11) . . ? N3 C1A C2A 109.22(11) . . ? C7A C1A C2A 110.68(12) . . ? N3 C1A C6A 107.98(11) . . ? C7A C1A C6A 109.84(11) . . ? C2A C1A C6A 109.86(11) . . ? C1A C2A C3A 108.59(12) . . ? C1A C2A H2A 110.0 . . ? C3A C2A H2A 110.0 . . ? C1A C2A H2B 110.0 . . ? C3A C2A H2B 110.0 . . ? H2A C2A H2B 108.4 . . ? C9A C3A C4A 109.75(13) . . ? C9A C3A C2A 109.34(13) . . ? C4A C3A C2A 109.32(12) . . ? C9A C3A H3A 109.5 . . ? C4A C3A H3A 109.5 . . ? C2A C3A H3A 109.5 . . ? C5A C4A C3A 109.61(12) . . ? C5A C4A H4A 109.7 . . ? C3A C4A H4A 109.7 . . ? C5A C4A H4B 109.7 . . ? C3A C4A H4B 109.7 . . ? H4A C4A H4B 108.2 . . ? C10A C5A C4A 109.64(12) . . ? C10A C5A C6A 109.47(12) . . ? C4A C5A C6A 109.16(12) . . ? C10A C5A H5A 109.5 . . ? C4A C5A H5A 109.5 . . ? C6A C5A H5A 109.5 . . ? C1A C6A C5A 108.82(11) . . ? 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 108.93(11) . . ? 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 . . ? C10A C8A C9A 109.81(12) . . ? C10A C8A C7A 109.13(11) . . ? C9A C8A C7A 109.11(12) . . ? C10A C8A H8A 109.6 . . ? C9A C8A H8A 109.6 . . ? C7A C8A H8A 109.6 . . ? C3A C9A C8A 109.69(12) . . ? C3A C9A H9A 109.7 . . ? C8A C9A H9A 109.7 . . ? C3A C9A H9B 109.7 . . ? C8A C9A H9B 109.7 . . ? H9A C9A H9B 108.2 . . ? C5A C10A C8A 109.69(12) . . ? C5A C10A H10A 109.7 . . ? C8A C10A H10A 109.7 . . ? C5A C10A H10B 109.7 . . ? C8A C10A H10B 109.7 . . ? H10A C10A H10B 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 O1 C1 1.2632(17) . ? O2 C1 1.2672(19) . ? C1 C2 1.5033(19) . ? C2 C7 1.387(2) . ? C2 C3 1.4264(19) . ? C3 N4 1.3415(19) . ? C3 N1 1.3748(19) . ? N4 C5 1.341(2) . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 C7 1.390(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? N1 C8 1.4006(19) . ? N1 H1N 0.883(18) . ? C8 C9 1.394(2) . ? C8 C13 1.401(2) . ? C9 C10 1.393(2) . ? C9 H9 0.9500 . ? C10 C11 1.384(2) . ? C10 C14 1.456(7) . ? C10 C141 1.534(6) . ? C11 C12 1.389(2) . ? C11 H11 0.9500 . ? C12 C13 1.382(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 F2 1.299(4) . ? C14 F1 1.305(5) . ? C14 F3 1.309(6) . ? C141 F21 1.299(4) . ? C141 F11 1.302(5) . ? C141 F31 1.307(6) . ? N3 C1A 1.5124(17) . ? N3 H3NA 0.945(19) . ? N3 H3NB 0.991(19) . ? N3 H3NC 0.964(19) . ? C1A C7A 1.526(2) . ? C1A C2A 1.526(2) . ? C1A C6A 1.5329(18) . ? C2A C3A 1.5413(19) . ? C2A H2A 0.9900 . ? C2A H2B 0.9900 . ? C3A C9A 1.529(2) . ? C3A C4A 1.535(2) . ? C3A H3A 1.0000 . ? C4A C5A 1.531(2) . ? C4A H4A 0.9900 . ? C4A H4B 0.9900 . ? C5A C10A 1.530(2) . ? C5A C6A 1.540(2) . ? C5A H5A 1.0000 . ? C6A H6A 0.9900 . ? C6A H6B 0.9900 . ? C7A C8A 1.5390(19) . ? C7A H7A 0.9900 . ? C7A H7B 0.9900 . ? C8A C10A 1.5327(19) . ? C8A C9A 1.535(2) . ? C8A H8A 1.0000 . ? C9A H9A 0.9900 . ? C9A H9B 0.9900 . ? C10A H10A 0.9900 . ? C10A H10B 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 0.883(18) 1.937(17) 2.6774(19) 140.6(16) . C9 H9 N4 0.95 2.29 2.897(2) 120.8 . N3 H3NA O1 0.945(19) 1.958(19) 2.8899(17) 168.2(16) 2_645 N3 H3NB O1 0.991(19) 1.82(2) 2.800(2) 168.8(16) 1_545 N3 H3NC O2 0.964(19) 1.815(19) 2.7745(18) 173.0(16) . 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 O1 C1 C2 C7 23.61(18) . . . . ? O2 C1 C2 C7 -157.88(12) . . . . ? O1 C1 C2 C3 -155.91(12) . . . . ? O2 C1 C2 C3 22.60(19) . . . . ? C7 C2 C3 N4 0.60(19) . . . . ? C1 C2 C3 N4 -179.87(12) . . . . ? C7 C2 C3 N1 -179.13(12) . . . . ? C1 C2 C3 N1 0.40(19) . . . . ? N1 C3 N4 C5 179.48(12) . . . . ? C2 C3 N4 C5 -0.25(19) . . . . ? C3 N4 C5 C6 0.1(2) . . . . ? N4 C5 C6 C7 -0.2(2) . . . . ? C3 C2 C7 C6 -0.75(19) . . . . ? C1 C2 C7 C6 179.71(12) . . . . ? C5 C6 C7 C2 0.6(2) . . . . ? N4 C3 N1 C8 -18.2(2) . . . . ? C2 C3 N1 C8 161.57(13) . . . . ? C3 N1 C8 C9 -1.3(2) . . . . ? C3 N1 C8 C13 -179.61(13) . . . . ? C13 C8 C9 C10 0.0(2) . . . . ? N1 C8 C9 C10 -178.22(13) . . . . ? C8 C9 C10 C11 -0.4(2) . . . . ? C8 C9 C10 C14 173.1(3) . . . . ? C8 C9 C10 C141 -175.0(3) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? C14 C10 C11 C12 -172.6(3) . . . . ? C141 C10 C11 C12 175.0(3) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C11 C12 C13 C8 -0.4(2) . . . . ? C9 C8 C13 C12 0.4(2) . . . . ? N1 C8 C13 C12 178.78(13) . . . . ? C11 C10 C14 F2 -14.9(7) . . . . ? C9 C10 C14 F2 171.7(5) . . . . ? C11 C10 C14 F1 -132.9(4) . . . . ? C9 C10 C14 F1 53.6(6) . . . . ? C11 C10 C14 F3 104.1(4) . . . . ? C9 C10 C14 F3 -69.4(4) . . . . ? C11 C10 C141 F21 18.9(5) . . . . ? C9 C10 C141 F21 -166.3(3) . . . . ? C11 C10 C141 F11 -99.7(6) . . . . ? C9 C10 C141 F11 75.0(7) . . . . ? C11 C10 C141 F31 142.5(5) . . . . ? C9 C10 C141 F31 -42.7(6) . . . . ? N3 C1A C2A C3A 179.45(11) . . . . ? C7A C1A C2A C3A -60.28(15) . . . . ? C6A C1A C2A C3A 61.18(15) . . . . ? C1A C2A C3A C9A 59.86(15) . . . . ? C1A C2A C3A C4A -60.32(16) . . . . ? C9A C3A C4A C5A -59.60(16) . . . . ? C2A C3A C4A C5A 60.32(16) . . . . ? C3A C4A C5A C10A 59.72(15) . . . . ? C3A C4A C5A C6A -60.20(15) . . . . ? N3 C1A C6A C5A 179.68(11) . . . . ? C7A C1A C6A C5A 60.67(15) . . . . ? C2A C1A C6A C5A -61.29(15) . . . . ? C10A C5A C6A C1A -59.79(15) . . . . ? C4A C5A C6A C1A 60.23(15) . . . . ? N3 C1A C7A C8A -179.35(11) . . . . ? C2A C1A C7A C8A 60.37(14) . . . . ? C6A C1A C7A C8A -61.11(14) . . . . ? C1A C7A C8A C10A 60.42(15) . . . . ? C1A C7A C8A C9A -59.56(15) . . . . ? C4A C3A C9A C8A 59.22(15) . . . . ? C2A C3A C9A C8A -60.69(15) . . . . ? C10A C8A C9A C3A -59.13(15) . . . . ? C7A C8A C9A C3A 60.44(15) . . . . ? C4A C5A C10A C8A -59.64(15) . . . . ? C6A C5A C10A C8A 60.08(15) . . . . ? C9A C8A C10A C5A 59.32(15) . . . . ? C7A C8A C10A C5A -60.24(15) . . . . ?