#------------------------------------------------------------------------------ #$Date: 2026-06-25 00:07:02 +0100 (Thu, 25 Jun 2026) $ #$Revision: 306639 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577429.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_1577429 loop_ _publ_author_name 'Schiele, Stefanie' 'Paschke, Ann-Sophie K.' 'Romiti, Giorgia' 'Morandi, Bill' _publ_section_title ; Direct access to 2-imidazolines from unactivated alkenes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03337G _journal_year 2026 _chemical_formula_moiety '2(C2 F3 O2), C10 H20 N4' _chemical_formula_sum 'C14 H20 F6 N4 O4' _chemical_formula_weight 422.34 _chemical_name_systematic '1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)butane (TFA salt)' _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 _atom_sites_solution_primary dual _audit_creation_date 2026-01-27 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2026-02-05 deposited with the CCDC. 2026-06-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.9510(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.99150(10) _cell_length_b 13.3535(2) _cell_length_c 13.3800(2) _cell_measurement_reflns_used 22659 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 79.1800 _cell_measurement_theta_min 3.3570 _cell_volume 880.97(3) _computing_cell_refinement 'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.144a 64-bit (release 23-01-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 46.00 112.00 0.50 0.15 -- 110.00-125.00 150.00 132 2 \w 41.00 67.00 0.50 0.15 -- 110.00-125.00 -30.00 52 3 \w 87.00 113.00 0.50 0.15 -- 110.00-125.00 -30.00 52 4 \w 72.00 98.00 0.50 0.15 -- 110.00-125.00 -60.00 52 5 \w 41.00 68.00 0.50 0.15 -- 110.00-125.00 -60.00 54 6 \w 44.00 80.00 0.50 0.15 -- 110.00-125.00-120.00 72 7 \w 49.00 106.00 0.50 0.15 -- 110.00 -99.00-180.00 114 8 \w 68.00 105.00 0.50 0.15 -- 110.00 -99.00 -60.00 74 9 \w 60.00 106.00 0.50 0.15 -- 110.00 -99.00 30.00 92 10 \w 38.00 63.00 0.50 0.15 -- 110.00 -57.00 0.00 50 11 \w 40.00 67.00 0.50 0.15 -- 110.00 -57.00 90.00 54 12 \w 40.00 68.00 0.50 0.15 -- 110.00 -57.00 30.00 56 13 \w 40.00 68.00 0.50 0.15 -- 110.00 -57.00 -30.00 56 14 \w 39.00 65.00 0.50 0.15 -- 110.00 -57.00 -60.00 52 15 \w 40.00 66.00 0.50 0.15 -- 110.00 -57.00 -90.00 52 16 \w 41.00 68.00 0.50 0.15 -- 110.00 -57.00-150.00 54 17 \w 40.00 67.00 0.50 0.15 -- 110.00 -57.00-180.00 54 18 \w 107.00 152.00 0.50 0.15 -- 110.00 19.00 30.00 90 19 \w 28.00 118.00 0.50 0.10 -- 52.00 77.00 161.95 180 20 \w 28.00 118.00 0.50 0.10 -- 52.00 77.00 161.95 180 21 \w 45.00 133.00 0.50 0.10 -- 68.00 76.00 137.69 176 22 \w 36.00 125.00 0.50 0.10 -- 60.00 77.00 77.75 178 23 \w 36.00 125.00 0.50 0.10 -- 60.00 77.00 35.38 178 24 \w 41.00 130.00 0.50 0.10 -- 64.00 75.00 -7.80 178 25 \w 41.00 130.00 0.50 0.10 -- 64.00 75.00 -7.80 178 26 \w 32.00 122.00 0.50 0.10 -- 56.00 77.00-139.44 180 27 \w 37.00 126.00 0.50 0.10 -- 60.00 75.00-110.75 178 28 \w 53.00 78.00 0.50 0.10 -- 76.00 75.00-131.55 50 29 \w 34.00 122.00 0.50 0.10 -- 56.00 74.00-152.63 176 30 \w 38.00 126.00 0.50 0.10 -- 60.00 74.00 -55.96 176 31 \w 54.00 142.00 0.50 0.10 -- 76.00 74.00 15.31 176 32 \w 34.00 122.00 0.50 0.10 -- 56.00 74.00 127.67 176 33 \w 46.00 134.00 0.50 0.10 -- 68.00 74.00 125.80 176 34 \w 38.00 126.00 0.50 0.10 -- 60.00 74.00 -55.96 176 35 \w 134.00 174.00 0.50 0.15 -- 110.00 57.00-180.00 80 36 \w 96.00 126.00 0.50 0.15 -- 110.00 57.00-180.00 60 37 \w 26.00 116.00 0.50 0.10 -- 49.37 77.00 0.00 180 38 \w 37.00 125.00 0.50 0.10 -- 49.37 38.00-150.00 176 39 \w 32.00 120.00 0.50 0.10 -- 49.37 62.00 -90.29 176 40 \w 37.00 125.00 0.50 0.10 -- 49.37 19.00 30.00 176 41 \w 37.00 125.00 0.50 0.10 -- 49.37 19.00 30.00 176 42 \w 34.00 121.00 0.50 0.10 -- 49.37 57.00 0.00 174 43 \w 34.00 121.00 0.50 0.10 -- 49.37 57.00 90.00 174 44 \w 32.00 120.00 0.50 0.10 -- 49.37 62.00 125.29 176 45 \w -122.00 -38.00 0.50 0.10 -- -49.37 178.00 -30.00 168 46 \w -38.00 26.00 0.50 0.10 -- -49.37 38.00 -30.00 128 47 \w -70.00 -28.00 0.50 0.15 -- -88.50 125.00-150.00 84 48 \w -122.00 -38.00 0.50 0.10 -- -49.37 178.00 -30.00 168 49 \w -107.00 -81.00 0.50 0.15 -- -88.50 77.00 150.00 52 50 \w -67.00 -25.00 0.50 0.15 -- -88.50 77.00 150.00 84 51 \w -125.00 -36.00 0.50 0.10 -- -49.37 -38.00 150.00 178 52 \w -89.00 -64.00 0.50 0.15 -- -88.00 -77.00 125.22 50 53 \w -109.00 -60.00 0.50 0.15 -- -84.00 -77.00 64.44 98 54 \w -91.00 -65.00 0.50 0.15 -- -88.50 -77.00 30.99 52 55 \w -115.00 -26.00 0.50 0.10 -- -49.37 -77.00 0.00 178 56 \w -153.00-125.00 0.50 0.15 -- -88.50 -77.00 30.99 56 57 \w -91.00 -65.00 0.50 0.15 -- -88.50 -77.00 38.51 52 58 \w -142.00 -52.00 0.50 0.10 -- -76.00 -77.00 -19.24 180 59 \w -153.00 -64.00 0.50 0.15 -- -88.00 -77.00 -36.94 178 60 \w -103.00 -65.00 0.50 0.15 -- -88.50 -77.00 -90.00 76 61 \w -108.00 -65.00 0.50 0.15 -- -88.50 -77.00-120.00 86 62 \w -137.00-111.00 0.50 0.15 -- -88.50 -77.00 -90.00 52 63 \w -90.00 -65.00 0.50 0.15 -- -88.50 -76.00 -5.84 50 64 \w -94.00 -67.00 0.50 0.15 -- -88.50 -76.00 -14.88 54 65 \w -150.00 -97.00 0.50 0.15 -- -88.50 -77.00 38.51 106 66 \w -153.00 -65.00 0.50 0.15 -- -88.50 -76.00 79.32 176 67 \w -92.00 -66.00 0.50 0.15 -- -88.50 -77.00 120.00 52 68 \w -142.00-115.00 0.50 0.15 -- -88.50 -76.00 -5.84 54 69 \w -148.00-122.00 0.50 0.15 -- -88.50 -76.00 -14.88 52 70 \w -155.00-101.00 0.50 0.15 -- -88.50 -73.00 -61.81 108 71 \w -97.00 -68.00 0.50 0.15 -- -88.50 -73.00 -61.81 58 72 \w -134.00 -45.00 0.50 0.10 -- -68.00 -75.00-107.87 178 73 \w -150.00-124.00 0.50 0.15 -- -88.50 -76.00-160.04 52 74 \w -93.00 -65.00 0.50 0.15 -- -88.50 -76.00-160.04 56 75 \w -93.00 -67.00 0.50 0.15 -- -88.00 -71.00-140.60 52 76 \w -155.00-100.00 0.50 0.15 -- -88.00 -71.00-140.60 110 77 \w -112.00 -66.00 0.50 0.15 -- -88.00 -72.00-106.37 92 78 \w -95.00 -69.00 0.50 0.15 -- -88.50 -69.00 -82.72 52 79 \w -155.00-115.00 0.50 0.15 -- -88.50 -69.00 -82.72 80 80 \w -82.00 -57.00 0.50 0.10 -- -76.00 -69.00 -65.86 50 81 \w -127.00 -68.00 0.50 0.15 -- -88.50 -69.00 93.21 118 82 \w -86.00 -57.00 0.50 0.10 -- -76.00 -68.00 128.93 58 83 \w -86.00 -57.00 0.50 0.10 -- -76.00 -68.00 139.88 58 84 \w -93.00 -67.00 0.50 0.15 -- -88.50 -72.00 174.17 52 85 \w -155.00-113.00 0.50 0.15 -- -88.50 -72.00 174.17 84 86 \w -137.00-111.00 0.50 0.10 -- -76.00 -68.00 128.93 52 87 \w -98.00 -70.00 0.50 0.15 -- -88.50 -65.00 34.51 56 88 \w -159.00 -77.00 0.50 0.15 -- -88.50 -58.00 134.42 164 89 \w -148.00-114.00 0.50 0.15 -- -88.50 -65.00 -1.40 68 90 \w -95.00 -70.00 0.50 0.15 -- -88.50 -65.00 -1.40 50 91 \w -96.00 -70.00 0.50 0.15 -- -88.50 -64.00-160.28 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.2658531000 _diffrn_orient_matrix_UB_12 0.0541101000 _diffrn_orient_matrix_UB_13 -0.0427446000 _diffrn_orient_matrix_UB_21 0.0424338000 _diffrn_orient_matrix_UB_22 -0.0276623000 _diffrn_orient_matrix_UB_23 -0.1082021000 _diffrn_orient_matrix_UB_31 -0.1585874000 _diffrn_orient_matrix_UB_32 -0.0980797000 _diffrn_orient_matrix_UB_33 0.0069213000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_unetI/netI 0.0115 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 32924 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.961 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 80.013 _diffrn_reflns_theta_min 4.707 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.400 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.592 _exptl_crystal_description block _exptl_crystal_F_000 436 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile' _exptl_crystal_size_max 0.118 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.055 _refine_diff_density_max 0.245 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 133 _refine_ls_number_reflns 1853 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0317 _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^)+(0.0345P)^2^+0.4261P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.0788 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1729 _reflns_number_total 1853 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03337g2.cif _cod_data_source_block bm210126_1_1 _cod_database_code 1577429 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C14H20F6N4O4 _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_max 0.921 _shelx_estimated_absorpt_t_min 0.850 _diffrn_oxdiff_ac3_digest_hkl 4168ca66c569c5a29b08e6a72298f386d34736 _diffrn_oxdiff_digest_hkl ; 432a11cebb6901607573a197a800a03bcfa186 ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H) groups 2. Restrained distances N1-H1 = N2-H2 0.93 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C4(H4B,H4A), C2(H2A,H2B), C3(H3A,H3B) ; _shelx_res_file ; TITL bm210126_1_1_a.res in P2(1)/c bm210126_1_1.res created by SHELXL-2019/3 at 13:39:19 on 27-Jan-2026 REM Old TITL bm210126_1_1 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.146, Rweak 0.021, Alpha 0.016 REM 0.983 for 90 systematic absences, Orientation as input REM Formula found by SHELXT: C7 N2 O2 F3 CELL 1.54184 4.9915 13.3535 13.38 90 98.951 90 ZERR 2 0.0001 0.0002 0.0002 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O UNIT 28 40 12 8 8 DFIX 0.93 N1 H1 N2 H2 L.S. 9 PLAN 20 SIZE 0.06 0.08 0.12 TEMP -173 CONF BOND list 4 fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.034500 0.426100 FVAR 0.89150 F1A 3 0.432044 0.223130 0.525137 11.00000 0.05090 0.03428 = 0.02052 0.00514 0.00185 -0.00554 F2A 3 0.077801 0.201873 0.415398 11.00000 0.02071 0.04381 = 0.04966 0.00367 0.01093 -0.00562 F3A 3 0.404602 0.096267 0.425543 11.00000 0.06122 0.01485 = 0.05714 0.00528 0.03384 0.00444 O2A 5 0.504120 0.212937 0.272438 11.00000 0.03150 0.02342 = 0.02031 -0.00115 0.00398 0.00675 O1A 5 0.512324 0.345999 0.375825 11.00000 0.03373 0.01687 = 0.03367 -0.00255 0.01713 -0.00410 N1 4 -0.115514 0.439473 0.273975 11.00000 0.01931 0.01775 = 0.01754 -0.00197 0.00615 -0.00228 H1 2 -0.236562 0.413904 0.308113 11.00000 -1.20000 N2 4 0.214581 0.533460 0.238047 11.00000 0.02042 0.01840 = 0.01825 -0.00034 0.00563 -0.00271 H2 2 0.311434 0.589771 0.238285 11.00000 -1.20000 C1 1 0.034120 0.519266 0.298843 11.00000 0.01804 0.01477 = 0.01519 0.00345 0.00134 0.00205 C5 1 -0.100386 0.538205 0.473268 11.00000 0.02073 0.01641 = 0.01593 -0.00158 0.00519 0.00283 AFIX 23 H5A 2 -0.134899 0.590199 0.522453 11.00000 -1.20000 H5B 2 -0.274558 0.504207 0.448885 11.00000 -1.20000 AFIX 0 C2A 1 0.471293 0.257189 0.351208 11.00000 0.01467 0.01829 = 0.02162 0.00041 0.00276 0.00290 C4 1 0.002011 0.588603 0.383602 11.00000 0.02753 0.01393 = 0.01824 0.00004 0.00499 0.00071 AFIX 23 H4B 2 -0.126435 0.642374 0.357324 11.00000 -1.20000 H4A 2 0.179330 0.620382 0.407997 11.00000 -1.20000 AFIX 0 C2 1 -0.030544 0.387304 0.187472 11.00000 0.02111 0.02176 = 0.01844 -0.00472 0.00445 -0.00031 AFIX 23 H2A 2 -0.183706 0.379725 0.131341 11.00000 -1.20000 H2B 2 0.045260 0.320402 0.207240 11.00000 -1.20000 AFIX 0 C1A 1 0.348797 0.194074 0.430088 11.00000 0.02134 0.01569 = 0.02563 -0.00072 0.00491 0.00026 C3 1 0.188119 0.457609 0.157919 11.00000 0.02201 0.02556 = 0.01858 -0.00402 0.00638 -0.00110 AFIX 23 H3A 2 0.361304 0.421658 0.157286 11.00000 -1.20000 H3B 2 0.129109 0.488033 0.090620 11.00000 -1.20000 AFIX 0 HKLF 4 REM bm210126_1_1_a.res in P2(1)/c REM wR2 = 0.0788, GooF = S = 1.056, Restrained GooF = 1.058 for all data REM R1 = 0.0317 for 1729 Fo > 4sig(Fo) and 0.0339 for all 1853 data REM 133 parameters refined using 2 restraints END WGHT 0.0343 0.4265 REM Highest difference peak 0.245, deepest hole -0.268, 1-sigma level 0.046 Q1 1 0.4068 0.2241 0.3892 11.00000 0.05 0.24 Q2 1 -0.0418 0.5604 0.4270 11.00000 0.05 0.24 Q3 1 0.5588 0.1143 0.4488 11.00000 0.05 0.22 Q4 1 0.0000 0.5000 0.5000 10.50000 0.05 0.21 Q5 1 0.0838 0.4192 0.1711 11.00000 0.05 0.21 Q6 1 0.0141 0.5551 0.3385 11.00000 0.05 0.21 Q7 1 0.1947 0.4993 0.1935 11.00000 0.05 0.19 Q8 1 0.1577 0.5226 0.2762 11.00000 0.05 0.17 Q9 1 -0.0860 0.4150 0.2295 11.00000 0.05 0.16 Q10 1 0.0976 0.5382 0.2581 11.00000 0.05 0.16 Q11 1 0.1244 0.1393 0.4065 11.00000 0.05 0.15 Q12 1 0.5488 0.1825 0.5059 11.00000 0.05 0.14 Q13 1 0.0023 0.4695 0.3048 11.00000 0.05 0.13 Q14 1 -0.1176 0.2605 0.4530 11.00000 0.05 0.11 Q15 1 -0.1679 0.3407 0.1459 11.00000 0.05 0.11 Q16 1 0.1702 0.7134 0.3582 11.00000 0.05 0.11 Q17 1 0.3172 0.4560 0.1130 11.00000 0.05 0.10 Q18 1 0.1747 0.7176 0.4355 11.00000 0.05 0.10 Q19 1 -0.2297 0.1532 0.4626 11.00000 0.05 0.10 Q20 1 0.3589 0.6034 0.4028 11.00000 0.05 0.10 ; _shelx_res_checksum 90949 _olex2_date_sample_data_collection 2026-01-26 _olex2_date_sample_submission 2026-01-26 _olex2_submission_original_sample_id bm210126_1_1 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.253 _oxdiff_exptl_absorpt_empirical_full_min 0.853 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 F1A F 0.43204(18) 0.22313(6) 0.52514(6) 0.0356(2) Uani 1 1 d . . . . . F2A F 0.07780(15) 0.20187(7) 0.41540(7) 0.0375(2) Uani 1 1 d . . . . . F3A F 0.4046(2) 0.09627(6) 0.42554(7) 0.0418(2) Uani 1 1 d . . . . . O2A O 0.50412(18) 0.21294(7) 0.27244(6) 0.0251(2) Uani 1 1 d . . . . . O1A O 0.51232(19) 0.34600(6) 0.37583(7) 0.0268(2) Uani 1 1 d . . . . . N1 N -0.11551(19) 0.43947(7) 0.27398(7) 0.0179(2) Uani 1 1 d D . . . . H1 H -0.237(3) 0.4139(11) 0.3081(11) 0.021 Uiso 1 1 d D U . . . N2 N 0.2146(2) 0.53346(8) 0.23805(7) 0.0187(2) Uani 1 1 d D . . . . H2 H 0.311(3) 0.5898(10) 0.2383(11) 0.022 Uiso 1 1 d D U . . . C1 C 0.0341(2) 0.51927(8) 0.29884(8) 0.0161(2) Uani 1 1 d . . . . . C5 C -0.1004(2) 0.53821(8) 0.47327(8) 0.0174(2) Uani 1 1 d . . . . . H5A H -0.134899 0.590199 0.522453 0.021 Uiso 1 1 calc R U . . . H5B H -0.274558 0.504207 0.448885 0.021 Uiso 1 1 calc R U . . . C2A C 0.4713(2) 0.25719(9) 0.35121(9) 0.0182(2) Uani 1 1 d . . . . . C4 C 0.0020(2) 0.58860(9) 0.38360(9) 0.0198(2) Uani 1 1 d . . . . . H4B H -0.126435 0.642374 0.357324 0.024 Uiso 1 1 calc R U . . . H4A H 0.179330 0.620382 0.407997 0.024 Uiso 1 1 calc R U . . . C2 C -0.0305(2) 0.38730(9) 0.18747(9) 0.0203(2) Uani 1 1 d . . . . . H2A H -0.183706 0.379725 0.131341 0.024 Uiso 1 1 calc R U . . . H2B H 0.045260 0.320402 0.207240 0.024 Uiso 1 1 calc R U . . . C1A C 0.3488(2) 0.19407(9) 0.43009(9) 0.0208(3) Uani 1 1 d . . . . . C3 C 0.1881(2) 0.45761(9) 0.15792(9) 0.0217(3) Uani 1 1 d . . . . . H3A H 0.361304 0.421658 0.157286 0.026 Uiso 1 1 calc R U . . . H3B H 0.129109 0.488033 0.090620 0.026 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 F1A 0.0509(5) 0.0343(5) 0.0205(4) 0.0051(3) 0.0019(3) -0.0055(4) F2A 0.0207(4) 0.0438(5) 0.0497(5) 0.0037(4) 0.0109(3) -0.0056(3) F3A 0.0612(6) 0.0148(4) 0.0571(6) 0.0053(4) 0.0338(5) 0.0044(4) O2A 0.0315(5) 0.0234(4) 0.0203(4) -0.0012(3) 0.0040(3) 0.0067(4) O1A 0.0337(5) 0.0169(4) 0.0337(5) -0.0025(4) 0.0171(4) -0.0041(4) N1 0.0193(5) 0.0177(5) 0.0175(5) -0.0020(4) 0.0062(4) -0.0023(4) N2 0.0204(5) 0.0184(5) 0.0182(5) -0.0003(4) 0.0056(4) -0.0027(4) C1 0.0180(5) 0.0148(5) 0.0152(5) 0.0034(4) 0.0013(4) 0.0020(4) C5 0.0207(5) 0.0164(5) 0.0159(5) -0.0016(4) 0.0052(4) 0.0028(4) C2A 0.0147(5) 0.0183(6) 0.0216(6) 0.0004(4) 0.0028(4) 0.0029(4) C4 0.0275(6) 0.0139(5) 0.0182(5) 0.0000(4) 0.0050(4) 0.0007(4) C2 0.0211(6) 0.0218(6) 0.0184(6) -0.0047(4) 0.0045(4) -0.0003(4) C1A 0.0213(6) 0.0157(6) 0.0256(6) -0.0007(4) 0.0049(5) 0.0003(4) C3 0.0220(6) 0.0256(6) 0.0186(6) -0.0040(5) 0.0064(4) -0.0011(5) 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' F F 0.0727 0.0534 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0286 0 0 -1 0.0267 -2 0 1 0.0413 0 1 0 0.0595 0 -1 0 0.0587 0 2 1 0.0527 1 2 1 0.0595 1 0 1 0.0406 1 0 -1 0.0396 -2 -7 1 0.0644 -3 1 -4 0.0434 0 -8 3 0.0516 2 -7 -1 0.0556 -2 0 8 0.0437 -2 -7 -3 0.0626 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 C1 N1 H1 126.3(10) . . ? C1 N1 C2 111.20(9) . . ? C2 N1 H1 122.0(10) . . ? C1 N2 H2 122.7(9) . . ? C1 N2 C3 111.07(10) . . ? C3 N2 H2 124.8(9) . . ? N1 C1 N2 112.12(10) . . ? N1 C1 C4 124.87(10) . . ? N2 C1 C4 122.99(10) . . ? C5 C5 H5A 109.1 3_566 . ? C5 C5 H5B 109.1 3_566 . ? C5 C5 C4 112.70(11) 3_566 . ? H5A C5 H5B 107.8 . . ? C4 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? O2A C2A C1A 115.97(10) . . ? O1A C2A O2A 130.02(11) . . ? O1A C2A C1A 113.96(10) . . ? C1 C4 C5 114.29(9) . . ? C1 C4 H4B 108.7 . . ? C1 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C5 C4 H4A 108.7 . . ? H4B C4 H4A 107.6 . . ? N1 C2 H2A 111.3 . . ? N1 C2 H2B 111.3 . . ? N1 C2 C3 102.51(9) . . ? H2A C2 H2B 109.2 . . ? C3 C2 H2A 111.3 . . ? C3 C2 H2B 111.3 . . ? F1A C1A F2A 105.96(10) . . ? F1A C1A F3A 106.93(10) . . ? F1A C1A C2A 113.22(10) . . ? F2A C1A C2A 110.74(10) . . ? F3A C1A F2A 106.35(10) . . ? F3A C1A C2A 113.14(10) . . ? N2 C3 C2 102.75(9) . . ? N2 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? C2 C3 H3A 111.2 . . ? C2 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? 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 F1A C1A 1.3327(14) . ? F2A C1A 1.3403(14) . ? F3A C1A 1.3388(14) . ? O2A C2A 1.2412(14) . ? O1A C2A 1.2393(15) . ? N1 H1 0.881(13) . ? N1 C1 1.3140(15) . ? N1 C2 1.4689(14) . ? N2 H2 0.894(13) . ? N2 C1 1.3180(15) . ? N2 C3 1.4659(15) . ? C1 C4 1.4919(16) . ? C5 C5 1.528(2) 3_566 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C4 1.5311(16) . ? C2A C1A 1.5488(16) . ? C4 H4B 0.9900 . ? C4 H4A 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5373(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? 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 O2A C2A C1A F1A 149.72(10) . . . . ? O2A C2A C1A F2A -91.43(12) . . . . ? O2A C2A C1A F3A 27.86(15) . . . . ? O1A C2A C1A F1A -32.74(14) . . . . ? O1A C2A C1A F2A 86.11(12) . . . . ? O1A C2A C1A F3A -154.60(11) . . . . ? N1 C1 C4 C5 31.29(16) . . . . ? N1 C2 C3 N2 5.62(11) . . . . ? N2 C1 C4 C5 -150.65(11) . . . . ? C1 N1 C2 C3 -4.94(12) . . . . ? C1 N2 C3 C2 -4.98(12) . . . . ? C5 C5 C4 C1 64.84(15) 3_566 . . . ? C2 N1 C1 N2 2.05(13) . . . . ? C2 N1 C1 C4 -179.72(10) . . . . ? C3 N2 C1 N1 2.09(13) . . . . ? C3 N2 C1 C4 -176.18(10) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0005 -0.0013 0.9987 -0.0426 -0.1080 0.0071 0.0005 0.0013 -0.9987 0.0426 0.1080 -0.0071 -1.9980 0.0061 0.9856 0.4894 -0.1916 0.3231 0.0000 1.0000 -0.0003 0.0541 -0.0276 -0.0981 -0.0000 -1.0000 0.0003 -0.0541 0.0276 0.0981 0.0004 2.0028 1.0000 0.0655 -0.1636 -0.1896 0.9982 1.9917 1.0140 -0.2009 -0.1225 -0.3466 0.9994 -0.0080 1.0025 -0.3090 -0.0658 -0.1508 0.9997 0.0041 -0.9994 -0.2228 0.1504 -0.1659 -1.7005 -7.3772 1.0355 0.0087 0.0199 1.0004 -2.6324 0.9906 -3.8187 0.9167 0.2741 0.2939 0.2665 -7.9438 3.2563 -0.6399 -0.1213 0.7594 2.0606 -6.6762 -1.2325 -0.8564 0.4055 0.3195 -1.9159 -0.1400 7.7121 0.1721 -0.9119 0.3709 -1.6240 -6.5057 -3.0586 0.2105 0.4420 0.8745