#------------------------------------------------------------------------------ #$Date: 2018-05-14 14:44:41 +0300 (Mon, 14 May 2018) $ #$Revision: 207762 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549411.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_1549411 loop_ _publ_author_name 'Carestia, Anthony' 'Ravelli, Davide' 'Alexanian, Erik' _publ_section_title ; Reagent-dictated site selectivity in intermolecular aliphatic C--H functionalizations using nitrogen-centered radicals ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC01756E _journal_year 2018 _chemical_formula_moiety 'C13 H12 Cl F6 N O' _chemical_formula_sum 'C13 H12 Cl F6 N O' _chemical_formula_weight 347.69 _chemical_name_common C _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_update_record ; 2017-06-01 deposited with the CCDC. 2018-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.648(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6263(6) _cell_length_b 16.9562(13) _cell_length_c 10.8430(9) _cell_measurement_reflns_used 328 _cell_measurement_temperature 100.(2) _cell_measurement_theta_max 33.6018 _cell_measurement_theta_min 3.9492 _cell_volume 1400.64(19) _computing_cell_refinement 'APEX3 v2016.5-0 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service v2013.12.0.0' _computing_data_reduction 'SAINT V8.37A (Bruker AXS Inc., 2015)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 786)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 100.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker-Nonius X8 Kappa APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0156 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 54325 _diffrn_reflns_theta_full 36.45 _diffrn_reflns_theta_max 36.45 _diffrn_reflns_theta_min 2.23 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.497 _exptl_crystal_size_mid 0.397 _exptl_crystal_size_min 0.332 _refine_diff_density_max 0.661 _refine_diff_density_min -0.371 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 6844 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0312 _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^)+(0.0456P)^2^+0.3763P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.0887 _reflns_number_gt 5844 _reflns_number_total 6844 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8sc01756e2.cif _cod_data_source_block rds582 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-Scan' changed to 'multi-scan' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 1549411 _shelx_res_file ; rds582_0m.res created by SHELXL-2014/7 TITL rds582_0m in P2(1)/c CELL 0.71073 7.6263 16.9562 10.843 90 92.6481 90 ZERR 4 0.0006 0.0013 0.0009 0 0.0035 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl F N O UNIT 52 48 4 24 4 4 L.S. 10 PLAN 5 SIZE 0.332 0.397 0.497 TEMP -173.15 BOND $h htab acta list 4 conf more -1 fmap 2 WGHT 0.045600 0.376300 FVAR 0.21248 CL1 3 0.063336 0.591607 0.952501 11.00000 0.01438 0.02799 = 0.01277 -0.00244 0.00409 -0.00741 F1 4 -0.028292 0.721731 0.546115 11.00000 0.04044 0.02022 = 0.03432 0.00595 0.00924 -0.00399 F2 4 -0.025882 0.727024 0.743772 11.00000 0.03554 0.01870 = 0.03434 -0.01154 -0.01663 0.00900 F3 4 -0.270844 0.720008 0.638290 11.00000 0.01800 0.02262 = 0.04619 0.00177 -0.00557 0.00855 F4 4 0.218953 0.365238 0.680553 11.00000 0.02968 0.01243 = 0.04415 -0.00288 -0.00349 0.00419 F5 4 0.215233 0.424947 0.855260 11.00000 0.02888 0.05103 = 0.01872 0.01307 0.00356 0.01695 F6 4 0.365695 0.471313 0.709803 11.00000 0.01256 0.01920 = 0.03737 0.00244 0.00307 0.00164 O1 6 0.312768 0.639760 0.669379 11.00000 0.01495 0.01926 = 0.01226 0.00171 0.00170 -0.00409 N1 5 0.238337 0.616034 0.867253 11.00000 0.00984 0.01583 = 0.00997 -0.00017 0.00111 -0.00287 C1 1 0.052515 0.565410 0.694230 11.00000 0.01026 0.01295 = 0.01076 -0.00089 -0.00009 -0.00098 C2 1 -0.098811 0.604612 0.649022 11.00000 0.01127 0.01524 = 0.01250 -0.00160 -0.00074 0.00085 C3 1 -0.244506 0.562573 0.602552 11.00000 0.01161 0.02291 = 0.01501 -0.00349 -0.00135 -0.00027 AFIX 43 H3 2 -0.347066 0.589976 0.573774 11.00000 -1.20000 AFIX 0 C4 1 -0.240037 0.480986 0.598258 11.00000 0.01369 0.02261 = 0.01868 -0.00567 -0.00065 -0.00470 AFIX 43 H4 2 -0.339570 0.452324 0.567150 11.00000 -1.20000 AFIX 0 C5 1 -0.089366 0.441286 0.639642 11.00000 0.01630 0.01592 = 0.01853 -0.00356 0.00191 -0.00455 AFIX 43 H5 2 -0.085259 0.385358 0.635471 11.00000 -1.20000 AFIX 0 C6 1 0.055707 0.482977 0.687211 11.00000 0.01205 0.01309 = 0.01321 -0.00045 0.00138 -0.00087 C7 1 0.212298 0.611481 0.741846 11.00000 0.01072 0.01228 = 0.01093 -0.00007 -0.00061 -0.00033 C8 1 -0.105812 0.693269 0.645033 11.00000 0.01510 0.01681 = 0.02070 -0.00126 -0.00328 0.00294 C9 1 0.213785 0.436358 0.733109 11.00000 0.01578 0.01507 = 0.01705 0.00156 0.00195 0.00123 C10 1 0.389491 0.660038 0.931000 11.00000 0.01052 0.01421 = 0.01167 -0.00084 -0.00099 -0.00145 C11 1 0.559514 0.622463 0.889808 11.00000 0.01113 0.03411 = 0.01943 -0.00634 -0.00063 0.00241 AFIX 137 H11A 2 0.563762 0.567068 0.915551 11.00000 -1.50000 H11B 2 0.660352 0.650679 0.927762 11.00000 -1.50000 H11C 2 0.563348 0.625572 0.799723 11.00000 -1.50000 AFIX 0 C12 1 0.381915 0.650823 1.070565 11.00000 0.01713 0.02343 = 0.01131 -0.00097 -0.00165 -0.00212 AFIX 137 H12A 2 0.276770 0.677215 1.098898 11.00000 -1.50000 H12B 2 0.486631 0.674667 1.110920 11.00000 -1.50000 H12C 2 0.377475 0.594665 1.091559 11.00000 -1.50000 AFIX 0 C13 1 0.376955 0.747166 0.896834 11.00000 0.02746 0.01471 = 0.02262 0.00216 -0.00632 -0.00535 AFIX 137 H13A 2 0.385132 0.753074 0.807377 11.00000 -1.50000 H13B 2 0.473244 0.776082 0.939299 11.00000 -1.50000 H13C 2 0.264434 0.768331 0.921872 11.00000 -1.50000 AFIX 0 HKLF 4 REM rds582_0m in P2(1)/c REM R1 = 0.0312 for 5844 Fo > 4sig(Fo) and 0.0385 for all 6844 data REM 202 parameters refined using 0 restraints END WGHT 0.0456 0.3762 REM Instructions for potential hydrogen bonds HTAB C11 O1 EQIV $1 x+1, -y+3/2, z+1/2 HTAB C12 F3_$1 HTAB C13 O1 REM Highest difference peak 0.661, deepest hole -0.371, 1-sigma level 0.059 Q1 1 0.1078 0.5605 0.9593 11.00000 0.05 0.66 Q2 1 -0.2451 0.5214 0.5977 11.00000 0.05 0.58 Q3 1 0.1414 0.4567 0.7127 11.00000 0.05 0.56 Q4 1 -0.1057 0.6506 0.6429 11.00000 0.05 0.55 Q5 1 0.0566 0.5243 0.6918 11.00000 0.05 0.54 ; _shelx_res_checksum 43006 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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_posn _atom_site_occupancy Cl Cl1 0.06334(2) 0.59161(2) 0.95250(2) 0.01827(5) Uani d . . 1 F F1 -0.02829(9) 0.72173(3) 0.54611(6) 0.03143(13) Uani d . . 1 F F2 -0.02588(8) 0.72702(3) 0.74377(6) 0.03009(14) Uani d . . 1 F F3 -0.27084(7) 0.72001(3) 0.63829(7) 0.02915(13) Uani d . . 1 F F4 0.21895(8) 0.36524(3) 0.68055(6) 0.02891(13) Uani d . . 1 F F5 0.21523(8) 0.42495(4) 0.85526(6) 0.03280(14) Uani d . . 1 F F6 0.36569(6) 0.47131(3) 0.70980(6) 0.02299(11) Uani d . . 1 O O1 0.31277(7) 0.63976(3) 0.66938(5) 0.01546(10) Uani d . . 1 N N1 0.23834(7) 0.61603(4) 0.86725(5) 0.01186(9) Uani d . . 1 C C1 0.05252(8) 0.56541(4) 0.69423(6) 0.01134(10) Uani d . . 1 C C2 -0.09881(9) 0.60461(4) 0.64902(6) 0.01304(11) Uani d . . 1 C C3 -0.24451(9) 0.56257(5) 0.60255(7) 0.01657(12) Uani d . . 1 H H3 -0.3471 0.59 0.5738 0.02 Uiso calc U R 1 C C4 -0.24004(10) 0.48099(5) 0.59826(8) 0.01837(13) Uani d . . 1 H H4 -0.3396 0.4523 0.5671 0.022 Uiso calc U R 1 C C5 -0.08937(10) 0.44129(4) 0.63964(7) 0.01688(12) Uani d . . 1 H H5 -0.0853 0.3854 0.6355 0.02 Uiso calc U R 1 C C6 0.05571(9) 0.48298(4) 0.68721(6) 0.01276(11) Uani d . . 1 C C7 0.21230(8) 0.61148(4) 0.74185(6) 0.01134(10) Uani d . . 1 C C8 -0.10581(10) 0.69327(4) 0.64503(8) 0.01766(13) Uani d . . 1 C C9 0.21378(10) 0.43636(4) 0.73311(7) 0.01593(12) Uani d . . 1 C C10 0.38949(8) 0.66004(4) 0.93100(6) 0.01218(10) Uani d . . 1 C C11 0.55951(10) 0.62246(6) 0.88981(8) 0.02160(15) Uani d . . 1 H H11A 0.5638 0.5671 0.9156 0.032 Uiso calc U R 1 H H11B 0.6604 0.6507 0.9278 0.032 Uiso calc U R 1 H H11C 0.5633 0.6256 0.7997 0.032 Uiso calc U R 1 C C12 0.38191(10) 0.65082(5) 1.07056(7) 0.01736(12) Uani d . . 1 H H12A 0.2768 0.6772 1.0989 0.026 Uiso calc U R 1 H H12B 0.4866 0.6747 1.1109 0.026 Uiso calc U R 1 H H12C 0.3775 0.5947 1.0916 0.026 Uiso calc U R 1 C C13 0.37696(12) 0.74717(5) 0.89683(8) 0.02183(15) Uani d . . 1 H H13A 0.3851 0.7531 0.8074 0.033 Uiso calc U R 1 H H13B 0.4732 0.7761 0.9393 0.033 Uiso calc U R 1 H H13C 0.2644 0.7683 0.9219 0.033 Uiso calc U R 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.01438(7) 0.02799(9) 0.01277(7) -0.00741(6) 0.00409(5) -0.00244(6) F1 0.0404(3) 0.0202(2) 0.0343(3) -0.0040(2) 0.0092(3) 0.0060(2) F2 0.0355(3) 0.0187(2) 0.0343(3) 0.0090(2) -0.0166(2) -0.0115(2) F3 0.0180(2) 0.0226(2) 0.0462(4) 0.00855(19) -0.0056(2) 0.0018(2) F4 0.0297(3) 0.0124(2) 0.0441(4) 0.00419(19) -0.0035(2) -0.0029(2) F5 0.0289(3) 0.0510(4) 0.0187(2) 0.0169(3) 0.0036(2) 0.0131(2) F6 0.01256(19) 0.0192(2) 0.0374(3) 0.00164(16) 0.00307(19) 0.00244(19) O1 0.0149(2) 0.0193(2) 0.0123(2) -0.00409(17) 0.00170(17) 0.00171(17) N1 0.0098(2) 0.0158(2) 0.0100(2) -0.00287(17) 0.00111(17) -0.00017(18) C1 0.0103(2) 0.0130(2) 0.0108(2) -0.00098(19) -0.00009(19) -0.00089(19) C2 0.0113(2) 0.0152(3) 0.0125(3) 0.0009(2) -0.00074(19) -0.0016(2) C3 0.0116(3) 0.0229(3) 0.0150(3) -0.0003(2) -0.0014(2) -0.0035(2) C4 0.0137(3) 0.0226(3) 0.0187(3) -0.0047(2) -0.0007(2) -0.0057(2) C5 0.0163(3) 0.0159(3) 0.0185(3) -0.0046(2) 0.0019(2) -0.0036(2) C6 0.0120(2) 0.0131(2) 0.0132(3) -0.00087(19) 0.0014(2) -0.0004(2) C7 0.0107(2) 0.0123(2) 0.0109(2) -0.00033(19) -0.00061(18) -0.00007(19) C8 0.0151(3) 0.0168(3) 0.0207(3) 0.0029(2) -0.0033(2) -0.0013(2) C9 0.0158(3) 0.0151(3) 0.0171(3) 0.0012(2) 0.0019(2) 0.0016(2) C10 0.0105(2) 0.0142(2) 0.0117(2) -0.00145(19) -0.00099(19) -0.0008(2) C11 0.0111(3) 0.0341(4) 0.0194(3) 0.0024(3) -0.0006(2) -0.0063(3) C12 0.0171(3) 0.0234(3) 0.0113(3) -0.0021(2) -0.0017(2) -0.0010(2) C13 0.0275(4) 0.0147(3) 0.0226(4) -0.0054(3) -0.0063(3) 0.0022(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 C10 123.69(5) C7 N1 Cl1 116.30(5) C10 N1 Cl1 118.03(4) C6 C1 C2 118.09(6) C6 C1 C7 121.11(6) C2 C1 C7 120.69(6) C3 C2 C1 120.91(7) C3 C2 C8 118.27(6) C1 C2 C8 120.78(6) C4 C3 C2 120.16(7) C4 C3 H3 119.9 C2 C3 H3 119.9 C3 C4 C5 119.66(7) C3 C4 H4 120.2 C5 C4 H4 120.2 C4 C5 C6 120.36(7) C4 C5 H5 119.8 C6 C5 H5 119.8 C5 C6 C1 120.78(6) C5 C6 C9 117.78(6) C1 C6 C9 121.43(6) O1 C7 N1 123.46(6) O1 C7 C1 120.08(6) N1 C7 C1 116.41(6) F2 C8 F3 106.99(7) F2 C8 F1 106.60(7) F3 C8 F1 106.47(7) F2 C8 C2 113.00(6) F3 C8 C2 111.87(6) F1 C8 C2 111.52(6) F4 C9 F6 106.08(6) F4 C9 F5 107.03(7) F6 C9 F5 106.49(7) F4 C9 C6 111.83(6) F6 C9 C6 113.10(6) F5 C9 C6 111.88(6) N1 C10 C13 109.20(6) N1 C10 C12 109.86(5) C13 C10 C12 109.60(6) N1 C10 C11 107.42(6) C13 C10 C11 112.15(7) C12 C10 C11 108.57(6) C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C10 C12 H12A 109.5 C10 C12 H12B 109.5 H12A C12 H12B 109.5 C10 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C10 C13 H13A 109.5 C10 C13 H13B 109.5 H13A C13 H13B 109.5 C10 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 N1 1.7091(6) F1 C8 1.3384(10) F2 C8 1.3361(10) F3 C8 1.3366(9) F4 C9 1.3351(9) F5 C9 1.3381(10) F6 C9 1.3358(9) O1 C7 1.2207(8) N1 C7 1.3673(9) N1 C10 1.5132(9) C1 C6 1.4001(10) C1 C2 1.4006(9) C1 C7 1.5177(9) C2 C3 1.3946(10) C2 C8 1.5048(11) C3 C4 1.3847(12) C3 H3 0.95 C4 C5 1.3882(11) C4 H4 0.95 C5 C6 1.3918(10) C5 H5 0.95 C6 C9 1.5068(10) C10 C13 1.5250(11) C10 C12 1.5251(10) C10 C11 1.5298(10) C11 H11A 0.98 C11 H11B 0.98 C11 H11C 0.98 C12 H12A 0.98 C12 H12B 0.98 C12 H12C 0.98 C13 H13A 0.98 C13 H13B 0.98 C13 H13C 0.98 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 C6 C1 C2 C3 2.32(10) C7 C1 C2 C3 178.52(6) C6 C1 C2 C8 -175.39(6) C7 C1 C2 C8 0.80(10) C1 C2 C3 C4 -1.29(11) C8 C2 C3 C4 176.49(7) C2 C3 C4 C5 -0.45(12) C3 C4 C5 C6 1.08(12) C4 C5 C6 C1 0.01(11) C4 C5 C6 C9 178.71(7) C2 C1 C6 C5 -1.68(10) C7 C1 C6 C5 -177.86(6) C2 C1 C6 C9 179.66(6) C7 C1 C6 C9 3.48(10) C10 N1 C7 O1 3.17(11) Cl1 N1 C7 O1 166.78(6) C10 N1 C7 C1 -179.43(6) Cl1 N1 C7 C1 -15.82(8) C6 C1 C7 O1 96.61(8) C2 C1 C7 O1 -79.47(9) C6 C1 C7 N1 -80.89(8) C2 C1 C7 N1 103.03(8) C3 C2 C8 F2 143.28(7) C1 C2 C8 F2 -38.94(10) C3 C2 C8 F3 22.46(10) C1 C2 C8 F3 -159.76(7) C3 C2 C8 F1 -96.66(8) C1 C2 C8 F1 81.11(9) C5 C6 C9 F4 23.78(9) C1 C6 C9 F4 -157.53(7) C5 C6 C9 F6 143.47(7) C1 C6 C9 F6 -37.83(9) C5 C6 C9 F5 -96.28(8) C1 C6 C9 F5 82.42(9) C7 N1 C10 C13 61.59(8) Cl1 N1 C10 C13 -101.76(6) C7 N1 C10 C12 -178.18(6) Cl1 N1 C10 C12 18.47(7) C7 N1 C10 C11 -60.26(9) Cl1 N1 C10 C11 136.40(6)