#------------------------------------------------------------------------------ #$Date: 2019-01-17 01:00:11 +0200 (Thu, 17 Jan 2019) $ #$Revision: 213166 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/28/7122849.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_7122849 loop_ _publ_author_name 'Cosimi, Elena' 'Trapp, Nils' 'Ebert, Marc-Olivier' 'Wennemers, Helma' _publ_section_title ; Combined Experimental and Theoretical Study of Long-Range H F Interactions in \a Fluoro Amides ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C8CC09987A _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C10 H12 F N O' _chemical_formula_sum 'C10 H12 F N O' _chemical_formula_weight 181.21 _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_space_group_name_H-M 'P 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-05-28 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497) ; _audit_update_record ; 2018-12-13 deposited with the CCDC. 2019-01-16 downloaded from the CCDC. ; _cell_angle_alpha 101.380(3) _cell_angle_beta 93.123(3) _cell_angle_gamma 94.168(3) _cell_formula_units_Z 2 _cell_length_a 5.7997(2) _cell_length_b 7.8020(3) _cell_length_c 10.7127(4) _cell_measurement_reflns_used 5610 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 78.2460 _cell_measurement_theta_min 4.2490 _cell_volume 472.78(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'CCD plate' _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.958 _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 -59.00 31.00 0.50 1.24 -- -30.00 89.00 -72.35 180 2 \w 5.00 32.00 0.50 1.24 -- 34.00 88.00-131.48 54 3 \w 27.00 115.00 0.50 1.24 -- 46.00 67.00-107.09 176 4 \w 98.00 178.00 0.50 4.95 -- 110.00 38.00 0.00 160 5 \w 149.00 176.00 0.50 4.95 -- 110.00 77.00 -60.00 54 6 \w 148.00 174.00 0.50 4.95 -- 110.00 77.00 0.00 52 7 \w 141.00 176.00 0.50 4.95 -- 110.00 57.00 60.00 70 8 \w 152.00 178.00 0.50 4.95 -- 110.00 38.00 90.00 52 9 \w 131.00 178.00 0.50 4.95 -- 110.00 57.00 150.00 94 10 \w 111.00 139.00 0.50 4.95 -- 110.00 38.00 120.00 56 11 \w 109.00 136.00 0.50 4.95 -- 110.00 38.00 90.00 54 12 \w 106.00 131.00 0.50 4.95 -- 110.00 38.00 150.00 50 13 \w 100.00 139.00 0.50 4.95 -- 110.00 57.00 90.00 78 14 \w 96.00 122.00 0.50 4.95 -- 110.00 57.00 60.00 52 15 \w 97.00 148.00 0.50 4.95 -- 110.00 57.00 120.00 102 16 \w 94.00 123.00 0.50 4.95 -- 110.00 -19.00 30.00 58 17 \w 98.00 129.00 0.50 4.95 -- 110.00 38.00 -30.00 62 18 \w 86.00 177.00 0.50 4.95 -- 110.00 77.00 30.00 182 19 \w 122.00 164.00 0.50 4.95 -- 110.00 77.00-120.00 84 20 \w 123.00 150.00 0.50 4.95 -- 110.00 77.00-150.00 54 21 \w 124.00 164.00 0.50 4.95 -- 110.00 77.00-180.00 80 22 \w 95.00 126.00 0.50 4.95 -- 110.00 57.00-180.00 62 23 \w 99.00 142.00 0.50 4.95 -- 110.00 38.00-120.00 86 24 \w 100.00 128.00 0.50 4.95 -- 110.00 38.00-180.00 56 25 \w 89.00 116.00 0.50 4.95 -- 110.00 77.00-120.00 54 26 \w 89.00 167.00 0.50 4.95 -- 110.00 77.00 -90.00 156 27 \w 96.00 130.00 0.50 4.95 -- 110.00 57.00 -90.00 68 28 \w 87.00 114.00 0.50 4.95 -- 110.00 77.00-150.00 54 29 \w 91.00 121.00 0.50 4.95 -- 110.00 77.00-180.00 60 30 \w 86.00 118.00 0.50 4.95 -- 110.00 77.00 -60.00 64 31 \w 91.00 118.00 0.50 4.95 -- 110.00 77.00 -30.00 54 32 \w 89.00 115.00 0.50 4.95 -- 110.00 77.00 0.00 52 33 \w 73.00 162.00 0.50 4.95 -- 94.00 70.00 34.30 178 34 \w 86.00 177.00 0.50 4.95 -- 110.00 77.00 120.00 182 35 \w 87.00 113.00 0.50 4.95 -- 110.00 77.00 90.00 52 36 \w 35.00 123.00 0.50 1.24 -- 47.62 38.00 90.00 176 37 \w 44.00 76.00 0.50 4.95 -- 110.00 -57.00 150.00 64 38 \w 51.00 82.00 0.50 4.95 -- 110.00 -57.00 90.00 62 39 \w 42.00 104.00 0.50 4.95 -- 110.00 -99.00 120.00 124 40 \w 46.00 82.00 0.50 4.95 -- 110.00 -57.00 0.00 72 41 \w 41.00 89.00 0.50 4.95 -- 110.00 -99.00 30.00 96 42 \w 84.00 120.00 0.50 4.95 -- 110.00-125.00 0.00 72 43 \w 80.00 119.00 0.50 4.95 -- 110.00-125.00-120.00 78 44 \w 52.00 130.00 0.50 4.95 -- 110.00 -77.00-150.00 156 45 \w 47.00 77.00 0.50 4.95 -- 110.00-125.00-120.00 60 46 \w 41.00 92.00 0.50 4.95 -- 110.00 -99.00 -30.00 102 47 \w 43.00 70.00 0.50 4.95 -- 110.00 -57.00 30.00 54 48 \w 46.00 73.00 0.50 4.95 -- 110.00-125.00 0.00 54 49 \w 35.00 123.00 0.50 1.24 -- 47.62 38.00-180.00 176 50 \w 25.00 113.00 0.50 1.24 -- 46.00 72.00 -20.53 176 51 \w 36.00 125.00 0.50 1.24 -- 58.00 73.00 37.65 178 52 \w 32.00 119.00 0.50 1.24 -- 47.62 57.00 150.00 174 53 \w 24.00 113.00 0.50 1.24 -- 46.00 73.00 115.42 178 54 \w 6.00 33.00 0.50 1.24 -- 34.00 87.00 1.93 54 55 \w 9.00 41.00 0.50 1.24 -- 34.00 81.00 -87.53 64 56 \w -95.00 -9.00 0.50 4.95 -- -70.00 125.00 30.00 172 57 \w -141.00 -53.00 0.50 4.95 -- -70.00 -59.00 -48.13 176 58 \w -113.00 -78.00 0.50 1.24 -- -47.62 -77.00 60.00 70 59 \w -133.00 -44.00 0.50 4.95 -- -66.00 -73.00 154.88 178 60 \w -118.00 -38.00 0.50 1.24 -- -47.62-178.00 60.00 160 61 \w -127.00 -38.00 0.50 1.24 -- -58.00 -67.00-137.30 178 62 \w -140.00 -51.00 0.50 4.95 -- -70.00 -64.00 -83.36 178 63 \w -138.00 -50.00 0.50 4.95 -- -70.00 -68.00 73.75 176 64 \w -139.00 -50.00 0.50 4.95 -- -70.00 -67.00 45.26 178 65 \w -138.00 -49.00 0.50 4.95 -- -70.00 -69.00-134.55 178 66 \w -140.00 -84.00 0.50 4.95 -- -70.00 -99.00-150.00 112 67 \w -139.00 -50.00 0.50 4.95 -- -70.00 -67.00 -90.68 178 68 \w -138.00 -50.00 0.50 4.95 -- -70.00 -68.00 17.21 176 69 \w -140.00 -51.00 0.50 4.95 -- -70.00 -64.00-160.40 178 70 \w -140.00 -51.00 0.50 4.95 -- -70.00 -64.00 -61.00 178 71 \w -140.00 -84.00 0.50 4.95 -- -70.00 -99.00 60.00 112 72 \w -140.00 -53.00 0.50 4.95 -- -70.00 -61.00 88.70 174 73 \w -138.00 -50.00 0.50 4.95 -- -70.00 -68.00 28.26 176 74 \w -139.00 -51.00 0.50 4.95 -- -70.00 -66.00 -11.30 176 75 \w -138.00 -50.00 0.50 4.95 -- -70.00 -68.00 152.37 176 76 \w -137.00 -49.00 0.50 4.95 -- -70.00 -71.00-172.31 176 ; _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 -0.0284100000 _diffrn_orient_matrix_UB_12 -0.0452934000 _diffrn_orient_matrix_UB_13 -0.1469308000 _diffrn_orient_matrix_UB_21 -0.1495341000 _diffrn_orient_matrix_UB_22 -0.1694906000 _diffrn_orient_matrix_UB_23 0.0054316000 _diffrn_orient_matrix_UB_31 -0.2193616000 _diffrn_orient_matrix_UB_32 0.1004334000 _diffrn_orient_matrix_UB_33 0.0027271000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_unetI/netI 0.0309 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.958 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 13622 _diffrn_reflns_point_group_measured_fraction_full 0.958 _diffrn_reflns_point_group_measured_fraction_max 0.884 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.974 _diffrn_reflns_theta_min 4.220 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.796 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017) 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 colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.273 _exptl_crystal_description plate _exptl_crystal_F_000 192 _exptl_crystal_size_max 0.164 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.016 _refine_diff_density_max 0.266 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details ; Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 243 _refine_ls_number_reflns 3651 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0406 _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^)+(0.0754P)^2^+0.0436P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1110 _refine_ls_wR_factor_ref 0.1196 _reflns_Friedel_coverage 0.846 _reflns_Friedel_fraction_full 0.916 _reflns_Friedel_fraction_max 0.811 _reflns_number_gt 3115 _reflns_number_total 3651 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8cc09987a2.cif _cod_data_source_block w230518_1_1 _cod_database_code 7122849 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C10H12FNO _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. ; _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N1B-H1B = N1A-H1A 0.93 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C2A(H2A), C2B(H2B) 3.b Secondary CH2 refined with riding coordinates: C4A(H4AA,H4AB), C4B(H4BA,H4BB) 3.c Aromatic/amide H refined with riding coordinates: C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B) 3.d Idealised Me refined as rotating group: C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC) ; _shelx_res_file ; TITL w230518_1_1_a.res in P1 w230518_1_1.res created by SHELXL-2018/3 at 09:24:34 on 28-May-2018 REM Old TITL w230518_1_1 in P1 REM SHELXT solution in P1 REM R1 0.105, Rweak 0.007, Alpha 0.000, Orientation as input REM Flack x = 0.103 ( 0.090 ) from Parsons' quotients REM Formula found by SHELXT: C20 N2 O2 F2 CELL 1.54184 5.7997 7.802 10.7127 101.38 93.123 94.168 ZERR 2 0.0002 0.0003 0.0004 0.003 0.003 0.003 LATT -1 SFAC C H F N O UNIT 20 24 2 2 2 DFIX 0.93 N1B H1B N1A H1A L.S. 8 0 0 PLAN 20 BOND $H list 4 fmap 2 53 acta REM REM REM WGHT 0.075400 0.043600 FVAR 1.45426 F1A 3 -0.001801 0.534601 0.231344 11.00000 0.04397 0.02491 = 0.04411 0.00291 -0.00506 0.00736 O1A 5 -0.001613 0.977347 0.388182 11.00000 0.03316 0.02505 = 0.04297 0.00563 0.00031 0.01146 N1A 4 0.249551 0.771400 0.402507 11.00000 0.02731 0.02184 = 0.03295 0.00674 0.00052 0.00521 H1A 2 0.288869 0.659250 0.371148 11.00000 -1.20000 C1A 1 -0.080048 0.765170 0.124738 11.00000 0.04961 0.03973 = 0.03617 0.00819 -0.00007 0.00954 AFIX 137 H1AA 2 0.076810 0.774938 0.100893 11.00000 -1.50000 H1AB 2 -0.141234 0.877784 0.134814 11.00000 -1.50000 H1AC 2 -0.172514 0.682854 0.059401 11.00000 -1.50000 AFIX 0 C2A 1 -0.085099 0.702080 0.249307 11.00000 0.02809 0.02716 = 0.03855 0.00480 0.00135 0.00977 AFIX 13 H2A 2 -0.245577 0.693238 0.273241 11.00000 -1.20000 AFIX 0 C3A 1 0.060031 0.827922 0.354457 11.00000 0.02587 0.02466 = 0.03303 0.00964 0.00445 0.00729 C4A 1 0.414533 0.886716 0.494170 11.00000 0.02291 0.02557 = 0.04032 0.00918 0.00274 0.00229 AFIX 23 H4AA 2 0.381940 1.007128 0.495049 11.00000 -1.20000 H4AB 2 0.568853 0.872760 0.465118 11.00000 -1.20000 AFIX 0 C5A 1 0.414316 0.856411 0.629217 11.00000 0.02456 0.01758 = 0.03675 0.00463 0.00209 0.00601 C6A 1 0.223571 0.777573 0.675334 11.00000 0.02745 0.02687 = 0.03703 0.00528 0.00218 0.00073 AFIX 43 H6A 2 0.090880 0.739200 0.621457 11.00000 -1.20000 AFIX 0 C7A 1 0.228253 0.755289 0.800599 11.00000 0.03168 0.03012 = 0.04240 0.00666 0.00682 -0.00086 AFIX 43 H7A 2 0.099461 0.701639 0.830036 11.00000 -1.20000 AFIX 0 C8A 1 0.423977 0.812635 0.881933 11.00000 0.03974 0.02906 = 0.03408 0.00882 0.00208 0.00386 AFIX 43 H8A 2 0.427852 0.797765 0.966024 11.00000 -1.20000 AFIX 0 C9A 1 0.615022 0.892853 0.836403 11.00000 0.02995 0.03478 = 0.04231 0.00716 -0.00657 0.00013 AFIX 43 H9A 2 0.746877 0.932843 0.890620 11.00000 -1.20000 AFIX 0 C10A 1 0.610085 0.913403 0.711557 11.00000 0.02314 0.02726 = 0.04780 0.00953 0.00183 -0.00083 AFIX 43 H10A 2 0.739502 0.966116 0.682030 11.00000 -1.20000 AFIX 0 F1B 3 0.491945 0.022838 0.232018 11.00000 0.04174 0.02441 = 0.04251 0.00504 -0.00512 0.00558 O1B 5 0.491674 0.472254 0.371743 11.00000 0.03513 0.02618 = 0.05538 0.00721 -0.00154 0.01230 N1B 4 0.737584 0.267424 0.398182 11.00000 0.02770 0.02099 = 0.03438 0.00761 -0.00045 0.00530 H1B 2 0.780509 0.153764 0.373598 11.00000 -1.20000 C1B 1 0.392307 0.240607 0.117879 11.00000 0.05693 0.04129 = 0.03673 0.00814 -0.00146 0.01564 AFIX 137 H1BA 2 0.545465 0.247978 0.088495 11.00000 -1.50000 H1BB 2 0.330521 0.352831 0.125969 11.00000 -1.50000 H1BC 2 0.294375 0.154750 0.057670 11.00000 -1.50000 AFIX 0 C2B 1 0.402613 0.187612 0.245897 11.00000 0.02845 0.02778 = 0.03668 0.00512 0.00075 0.00696 AFIX 13 H2B 2 0.245021 0.177637 0.273930 11.00000 -1.20000 AFIX 0 C3B 1 0.550895 0.321086 0.345782 11.00000 0.02547 0.02554 = 0.03693 0.01173 0.00561 0.00688 C4B 1 0.901741 0.388277 0.488194 11.00000 0.02661 0.02651 = 0.04097 0.00884 0.00106 0.00053 AFIX 23 H4BA 2 0.866491 0.507617 0.487021 11.00000 -1.20000 H4BB 2 1.056758 0.375069 0.460001 11.00000 -1.20000 AFIX 0 C5B 1 0.898573 0.360049 0.623476 11.00000 0.02421 0.02199 = 0.03689 0.00436 -0.00126 -0.00061 C6B 1 0.721074 0.415859 0.699932 11.00000 0.02200 0.02520 = 0.04489 0.00595 0.00058 0.00287 AFIX 43 H6B 2 0.598590 0.467209 0.666357 11.00000 -1.20000 AFIX 0 C7B 1 0.725157 0.395760 0.824709 11.00000 0.02777 0.03222 = 0.04321 0.00352 0.00660 0.00050 AFIX 43 H7B 2 0.605063 0.433014 0.874687 11.00000 -1.20000 AFIX 0 C8B 1 0.907778 0.320051 0.876708 11.00000 0.03502 0.03322 = 0.03342 0.00861 0.00194 -0.00560 AFIX 43 H8B 2 0.911519 0.308458 0.961530 11.00000 -1.20000 AFIX 0 C9B 1 1.083611 0.262226 0.801069 11.00000 0.02881 0.02955 = 0.04327 0.00901 -0.00238 0.00367 AFIX 43 H9B 2 1.205379 0.210276 0.834766 11.00000 -1.20000 AFIX 0 C10B 1 1.078621 0.281529 0.675506 11.00000 0.02605 0.02594 = 0.04074 0.00390 0.00210 0.00231 AFIX 43 H10B 2 1.196960 0.241597 0.625088 11.00000 -1.20000 AFIX 0 HKLF 4 REM w230518_1_1_a.res in P1 REM wR2 = 0.1196, GooF = S = 1.060, Restrained GooF = 1.059 for all data REM R1 = 0.0406 for 3115 Fo > 4sig(Fo) and 0.0483 for all 3651 data REM 243 parameters refined using 5 restraints END WGHT 0.0754 0.0436 REM Highest difference peak 0.266, deepest hole -0.292, 1-sigma level 0.046 Q1 1 0.3979 0.8797 0.5672 11.00000 0.05 0.27 Q2 1 0.3071 0.8117 0.5013 11.00000 0.05 0.24 Q3 1 0.8909 0.3831 0.5572 11.00000 0.05 0.24 Q4 1 0.7682 0.2980 0.4974 11.00000 0.05 0.22 Q5 1 0.7361 0.2686 0.2989 11.00000 0.05 0.22 Q6 1 0.4951 0.0378 0.3340 11.00000 0.05 0.22 Q7 1 -0.0047 0.5473 0.3396 11.00000 0.05 0.21 Q8 1 -0.0082 0.9652 0.2889 11.00000 0.05 0.21 Q9 1 -0.0135 0.4983 0.1371 11.00000 0.05 0.20 Q10 1 0.4765 -0.0008 0.1337 11.00000 0.05 0.20 Q11 1 0.4887 0.4572 0.2796 11.00000 0.05 0.20 Q12 1 0.2394 0.7674 0.3018 11.00000 0.05 0.19 Q13 1 0.0205 1.0031 0.4802 11.00000 0.05 0.18 Q14 1 0.6063 0.9200 0.9645 11.00000 0.05 0.17 Q15 1 0.4309 0.2657 0.2046 11.00000 0.05 0.17 Q16 1 0.4593 0.8979 0.7340 11.00000 0.05 0.17 Q17 1 0.4605 0.2503 0.3124 11.00000 0.05 0.15 Q18 1 1.1184 0.3168 0.9187 11.00000 0.05 0.15 Q19 1 0.2152 0.7658 0.5573 11.00000 0.05 0.15 Q20 1 0.3668 0.1794 0.1594 11.00000 0.05 0.15 ; _shelx_res_checksum 58355 _olex2_date_sample_data_collection 2018-05-23 _olex2_date_sample_submission 2018-05-23 _olex2_submission_original_sample_id w230518_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 1.858 _oxdiff_exptl_absorpt_empirical_full_min 0.667 loop_ _space_group_symop_operation_xyz 'x, y, z' 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 F1A F -0.0018(3) 0.5346(2) 0.23134(16) 0.0383(4) Uani 1 1 d . O1A O -0.0016(4) 0.9773(3) 0.38818(19) 0.0335(5) Uani 1 1 d . N1A N 0.2496(4) 0.7714(3) 0.4025(2) 0.0271(5) Uani 1 1 d D H1A H 0.289(6) 0.659(3) 0.371(3) 0.033 Uiso 1 1 d DR C1A C -0.0800(7) 0.7652(5) 0.1247(3) 0.0416(8) Uani 1 1 d . H1AA H 0.076810 0.774938 0.100893 0.062 Uiso 1 1 calc GR H1AB H -0.141234 0.877784 0.134814 0.062 Uiso 1 1 calc GR H1AC H -0.172514 0.682854 0.059401 0.062 Uiso 1 1 calc GR C2A C -0.0851(5) 0.7021(4) 0.2493(3) 0.0312(6) Uani 1 1 d . H2A H -0.245577 0.693238 0.273241 0.037 Uiso 1 1 calc R C3A C 0.0600(5) 0.8279(3) 0.3545(3) 0.0270(6) Uani 1 1 d . C4A C 0.4145(5) 0.8867(4) 0.4942(3) 0.0292(6) Uani 1 1 d . H4AA H 0.381940 1.007128 0.495049 0.035 Uiso 1 1 calc R H4AB H 0.568853 0.872760 0.465118 0.035 Uiso 1 1 calc R C5A C 0.4143(5) 0.8564(3) 0.6292(3) 0.0262(6) Uani 1 1 d . C6A C 0.2236(5) 0.7776(4) 0.6753(3) 0.0307(6) Uani 1 1 d . H6A H 0.090880 0.739200 0.621457 0.037 Uiso 1 1 calc R C7A C 0.2283(5) 0.7553(4) 0.8006(3) 0.0348(7) Uani 1 1 d . H7A H 0.099461 0.701639 0.830036 0.042 Uiso 1 1 calc R C8A C 0.4240(6) 0.8126(4) 0.8819(3) 0.0339(7) Uani 1 1 d . H8A H 0.427852 0.797765 0.966024 0.041 Uiso 1 1 calc R C9A C 0.6150(5) 0.8929(4) 0.8364(3) 0.0362(7) Uani 1 1 d . H9A H 0.746877 0.932843 0.890620 0.043 Uiso 1 1 calc R C10A C 0.6101(5) 0.9134(4) 0.7116(3) 0.0326(7) Uani 1 1 d . H10A H 0.739502 0.966116 0.682030 0.039 Uiso 1 1 calc R F1B F 0.4919(3) 0.0228(2) 0.23202(16) 0.0366(4) Uani 1 1 d . O1B O 0.4917(4) 0.4723(3) 0.3717(2) 0.0387(5) Uani 1 1 d . N1B N 0.7376(4) 0.2674(3) 0.3982(2) 0.0274(5) Uani 1 1 d D H1B H 0.781(6) 0.154(3) 0.374(3) 0.033 Uiso 1 1 d DR C1B C 0.3923(7) 0.2406(5) 0.1179(3) 0.0446(8) Uani 1 1 d . H1BA H 0.545465 0.247978 0.088495 0.067 Uiso 1 1 calc GR H1BB H 0.330521 0.352831 0.125969 0.067 Uiso 1 1 calc GR H1BC H 0.294375 0.154750 0.057670 0.067 Uiso 1 1 calc GR C2B C 0.4026(5) 0.1876(4) 0.2459(3) 0.0310(6) Uani 1 1 d . H2B H 0.245021 0.177637 0.273930 0.037 Uiso 1 1 calc R C3B C 0.5509(5) 0.3211(3) 0.3458(3) 0.0282(6) Uani 1 1 d . C4B C 0.9017(5) 0.3883(4) 0.4882(3) 0.0312(6) Uani 1 1 d . H4BA H 0.866491 0.507617 0.487021 0.037 Uiso 1 1 calc R H4BB H 1.056758 0.375069 0.460001 0.037 Uiso 1 1 calc R C5B C 0.8986(5) 0.3600(4) 0.6235(3) 0.0282(6) Uani 1 1 d . C6B C 0.7211(5) 0.4159(4) 0.6999(3) 0.0309(6) Uani 1 1 d . H6B H 0.598590 0.467209 0.666357 0.037 Uiso 1 1 calc R C7B C 0.7252(5) 0.3958(4) 0.8247(3) 0.0349(7) Uani 1 1 d . H7B H 0.605063 0.433014 0.874687 0.042 Uiso 1 1 calc R C8B C 0.9078(6) 0.3201(4) 0.8767(3) 0.0341(7) Uani 1 1 d . H8B H 0.911519 0.308458 0.961530 0.041 Uiso 1 1 calc R C9B C 1.0836(5) 0.2622(4) 0.8011(3) 0.0338(7) Uani 1 1 d . H9B H 1.205379 0.210276 0.834766 0.041 Uiso 1 1 calc R C10B C 1.0786(5) 0.2815(4) 0.6755(3) 0.0313(6) Uani 1 1 d . H10B H 1.196960 0.241597 0.625088 0.038 Uiso 1 1 calc R 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 0.0440(11) 0.0249(9) 0.0441(10) 0.0029(7) -0.0051(8) 0.0074(7) O1A 0.0332(11) 0.0250(10) 0.0430(12) 0.0056(8) 0.0003(9) 0.0115(8) N1A 0.0273(13) 0.0218(11) 0.0330(12) 0.0067(9) 0.0005(9) 0.0052(9) C1A 0.050(2) 0.0397(18) 0.0362(16) 0.0082(13) -0.0001(14) 0.0095(15) C2A 0.0281(15) 0.0272(14) 0.0386(16) 0.0048(11) 0.0014(12) 0.0098(12) C3A 0.0259(15) 0.0247(14) 0.0330(14) 0.0096(11) 0.0045(11) 0.0073(11) C4A 0.0229(14) 0.0256(14) 0.0403(15) 0.0092(11) 0.0027(11) 0.0023(11) C5A 0.0246(14) 0.0176(12) 0.0367(15) 0.0046(11) 0.0021(11) 0.0060(11) C6A 0.0275(15) 0.0269(14) 0.0370(15) 0.0053(12) 0.0022(12) 0.0007(12) C7A 0.0317(16) 0.0301(16) 0.0424(16) 0.0067(13) 0.0068(12) -0.0009(13) C8A 0.0397(18) 0.0291(15) 0.0341(15) 0.0088(12) 0.0021(12) 0.0039(13) C9A 0.0300(16) 0.0348(16) 0.0423(17) 0.0072(13) -0.0066(13) 0.0001(13) C10A 0.0231(15) 0.0273(15) 0.0478(17) 0.0095(13) 0.0018(12) -0.0008(12) F1B 0.0417(10) 0.0244(9) 0.0425(10) 0.0050(7) -0.0051(7) 0.0056(7) O1B 0.0351(12) 0.0262(10) 0.0554(14) 0.0072(9) -0.0015(10) 0.0123(9) N1B 0.0277(13) 0.0210(11) 0.0344(12) 0.0076(9) -0.0005(9) 0.0053(9) C1B 0.057(2) 0.0413(19) 0.0367(17) 0.0081(14) -0.0015(15) 0.0156(17) C2B 0.0284(15) 0.0278(15) 0.0367(15) 0.0051(12) 0.0008(11) 0.0070(12) C3B 0.0255(14) 0.0255(14) 0.0369(15) 0.0117(12) 0.0056(12) 0.0069(11) C4B 0.0266(14) 0.0265(14) 0.0410(16) 0.0088(11) 0.0011(12) 0.0005(11) C5B 0.0242(15) 0.0220(13) 0.0369(15) 0.0044(11) -0.0013(12) -0.0006(12) C6B 0.0220(14) 0.0252(14) 0.0449(17) 0.0060(12) 0.0006(12) 0.0029(12) C7B 0.0278(15) 0.0322(15) 0.0432(17) 0.0035(12) 0.0066(12) 0.0005(12) C8B 0.0350(17) 0.0332(16) 0.0334(15) 0.0086(12) 0.0019(12) -0.0056(14) C9B 0.0288(16) 0.0296(15) 0.0433(17) 0.0090(13) -0.0024(13) 0.0037(12) C10B 0.0260(15) 0.0259(14) 0.0407(16) 0.0039(12) 0.0021(12) 0.0023(12) 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 -5 1 0.0454 3 3 -1 0.0450 0 5 -1 0.0399 -4 0 1 0.0407 0 0 7 0.0081 0 0 -7 0.0081 -2 -4 1 0.0360 -1 1 -6 0.0206 -3 -1 -4 0.0278 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C3A N1A H1A 120(2) C3A N1A C4A 122.1(2) C4A N1A H1A 117(2) H1AA C1A H1AB 109.5 H1AA C1A H1AC 109.5 H1AB C1A H1AC 109.5 C2A C1A H1AA 109.5 C2A C1A H1AB 109.5 C2A C1A H1AC 109.5 F1A C2A C1A 108.5(2) F1A C2A H2A 108.9 F1A C2A C3A 110.4(2) C1A C2A H2A 108.9 C3A C2A C1A 111.0(2) C3A C2A H2A 108.9 O1A C3A N1A 124.3(3) O1A C3A C2A 118.2(2) N1A C3A C2A 117.5(2) N1A C4A H4AA 108.5 N1A C4A H4AB 108.5 N1A C4A C5A 115.2(2) H4AA C4A H4AB 107.5 C5A C4A H4AA 108.5 C5A C4A H4AB 108.5 C6A C5A C4A 122.5(2) C6A C5A C10A 118.5(3) C10A C5A C4A 118.9(2) C5A C6A H6A 119.6 C7A C6A C5A 120.9(3) C7A C6A H6A 119.6 C6A C7A H7A 119.9 C8A C7A C6A 120.2(3) C8A C7A H7A 119.9 C7A C8A H8A 120.4 C7A C8A C9A 119.2(3) C9A C8A H8A 120.4 C8A C9A H9A 119.8 C10A C9A C8A 120.4(3) C10A C9A H9A 119.8 C5A C10A H10A 119.6 C9A C10A C5A 120.8(3) C9A C10A H10A 119.6 C3B N1B H1B 122(2) C3B N1B C4B 121.8(2) C4B N1B H1B 116(2) H1BA C1B H1BB 109.5 H1BA C1B H1BC 109.5 H1BB C1B H1BC 109.5 C2B C1B H1BA 109.5 C2B C1B H1BB 109.5 C2B C1B H1BC 109.5 F1B C2B C1B 108.6(2) F1B C2B H2B 108.8 F1B C2B C3B 110.1(2) C1B C2B H2B 108.8 C1B C2B C3B 111.8(2) C3B C2B H2B 108.8 O1B C3B N1B 124.5(3) O1B C3B C2B 118.1(2) N1B C3B C2B 117.4(2) N1B C4B H4BA 108.8 N1B C4B H4BB 108.8 N1B C4B C5B 113.7(2) H4BA C4B H4BB 107.7 C5B C4B H4BA 108.8 C5B C4B H4BB 108.8 C6B C5B C4B 121.2(3) C6B C5B C10B 118.6(3) C10B C5B C4B 120.2(3) C5B C6B H6B 119.7 C7B C6B C5B 120.6(3) C7B C6B H6B 119.7 C6B C7B H7B 119.8 C6B C7B C8B 120.5(3) C8B C7B H7B 119.8 C7B C8B H8B 120.3 C9B C8B C7B 119.4(3) C9B C8B H8B 120.3 C8B C9B H9B 120.0 C10B C9B C8B 120.1(3) C10B C9B H9B 120.0 C5B C10B H10B 119.6 C9B C10B C5B 120.8(3) C9B C10B H10B 119.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1A C2A 1.407(3) O1A C3A 1.235(3) N1A H1A 0.92(2) N1A C3A 1.329(4) N1A C4A 1.454(3) C1A H1AA 0.9600 C1A H1AB 0.9600 C1A H1AC 0.9600 C1A C2A 1.512(4) C2A H2A 0.9800 C2A C3A 1.510(4) C4A H4AA 0.9700 C4A H4AB 0.9700 C4A C5A 1.511(4) C5A C6A 1.388(4) C5A C10A 1.388(4) C6A H6A 0.9300 C6A C7A 1.386(4) C7A H7A 0.9300 C7A C8A 1.383(4) C8A H8A 0.9300 C8A C9A 1.391(5) C9A H9A 0.9300 C9A C10A 1.377(4) C10A H10A 0.9300 F1B C2B 1.405(3) O1B C3B 1.235(4) N1B H1B 0.93(2) N1B C3B 1.325(4) N1B C4B 1.461(4) C1B H1BA 0.9600 C1B H1BB 0.9600 C1B H1BC 0.9600 C1B C2B 1.508(4) C2B H2B 0.9800 C2B C3B 1.516(4) C4B H4BA 0.9700 C4B H4BB 0.9700 C4B C5B 1.509(4) C5B C6B 1.392(4) C5B C10B 1.393(4) C6B H6B 0.9300 C6B C7B 1.375(4) C7B H7B 0.9300 C7B C8B 1.392(5) C8B H8B 0.9300 C8B C9B 1.383(5) C9B H9B 0.9300 C9B C10B 1.382(4) C10B H10B 0.9300 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 -0.0006 -5.0024 0.9984 0.0799 0.8534 -0.4996 3.0004 3.0027 -0.9979 -0.0746 -0.9630 -0.3593 0.0006 5.0024 -0.9984 -0.0799 -0.8534 0.4996 -4.0002 -0.0010 0.9982 -0.0330 0.6038 0.8801 -0.0035 0.0106 6.9949 -1.0281 0.0367 0.0209 0.0035 -0.0106 -6.9949 1.0281 -0.0367 -0.0209 -2.0005 -4.0029 0.9980 0.0915 0.9830 0.0395 -0.9969 0.9910 -5.9957 0.8644 -0.0515 0.3019 -2.9978 -1.0087 -3.9981 0.7183 0.5975 0.5454