#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:49:40 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253792 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126495.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_7126495 loop_ _publ_author_name 'Zhang, Wei' 'Lin, Jin-Hong' 'Zhang, Pengfei' 'Xiao, Ji-Chang' _publ_section_title ; A convenient reagent for the conversion of aldoximes into nitriles and isonitriles. ; _journal_issue 46 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6221 _journal_page_last 6224 _journal_paper_doi 10.1039/d0cc00188k _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C4 H2 F3 N3 O4 S' _chemical_formula_sum 'C4 H2 F3 N3 O4 S' _chemical_formula_weight 245.15 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2020-04-01 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-04-13 deposited with the CCDC. 2020-05-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.199(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.0715(9) _cell_length_b 5.7257(4) _cell_length_c 12.5111(10) _cell_measurement_reflns_used 6657 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 54.76 _cell_measurement_theta_min 3.25 _cell_volume 848.27(11) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _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_temperature 169.97 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0713 _diffrn_reflns_av_unetI/netI 0.0531 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7322 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.921 _diffrn_reflns_theta_min 3.247 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.610 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.4228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1849 before and 0.1132 after correction. The Ratio of minimum to maximum transmission is 0.5631. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.920 _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.644 _refine_diff_density_min -0.835 _refine_diff_density_rms 0.163 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1595 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.131 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0589 _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^)+(0.0986P)^2^+0.2799P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1458 _refine_ls_wR_factor_ref 0.1481 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1513 _reflns_number_total 1595 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc00188k2.cif _cod_data_source_block mj20105_0m _cod_depositor_comments 'Adding full bibliography for 7126495.cif.' _cod_database_code 7126495 _shelx_shelxl_version_number 2016/6 _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 0.859 _shelx_estimated_absorpt_t_min 0.818 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C3(H3) ; _shelx_res_file ; TITL mj20105_0m_a.res in P2(1)/c mj20105_0m.res created by SHELXL-2016/6 at 09:06:31 on 01-Apr-2020 REM Old TITL mj20105_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.144, Rweak 0.004, Alpha 0.034, Orientation as input REM Formula found by SHELXT: C7 N O3 F3 S CELL 1.34139 12.0715 5.7257 12.5111 90 101.199 90 ZERR 4 0.0009 0.0004 0.001 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O S DISP C 0.0148 0.007 57.7477 DISP F 0.0599 0.0411 317.6292 DISP H -0 0 0.6481 DISP N 0.0253 0.0136 110.5121 DISP O 0.0412 0.025 193.9543 DISP S 0.2924 0.4247 3241.7632 UNIT 16 8 12 12 16 4 L.S. 4 PLAN 20 SIZE 0.06 0.06 0.08 TEMP -103.18 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.098600 0.279900 FVAR 1.03827 S1 6 0.843718 0.675458 0.698687 11.00000 0.02452 0.02892 = 0.02475 0.00361 0.00848 -0.00012 F1 3 0.992492 0.707386 0.576901 11.00000 0.03522 0.07019 = 0.05475 0.01442 0.02671 0.01394 F2 3 0.821989 0.666273 0.489032 11.00000 0.05995 0.07219 = 0.02832 -0.00779 0.01101 0.00183 F3 3 0.876530 0.995551 0.560440 11.00000 0.06799 0.03569 = 0.06467 0.01689 0.03621 0.00167 O1 5 0.826719 0.432209 0.690966 11.00000 0.03663 0.02634 = 0.06272 0.01035 0.01831 0.00527 O2 5 0.915645 0.788079 0.785914 11.00000 0.03081 0.06735 = 0.02934 -0.00589 0.00375 -0.00230 O3 5 0.385721 0.729327 0.535421 11.00000 0.03646 0.04849 = 0.03207 -0.01209 0.00048 0.00164 O4 5 0.362325 1.031857 0.632779 11.00000 0.03580 0.04439 = 0.04222 -0.00614 0.00654 0.01616 N1 4 0.717550 0.803353 0.685615 11.00000 0.02508 0.02176 = 0.02442 -0.00201 0.00881 -0.00225 N2 4 0.588895 1.061831 0.713344 11.00000 0.03560 0.02185 = 0.03340 -0.00635 0.01266 -0.00197 N3 4 0.421628 0.883012 0.601494 11.00000 0.03198 0.03054 = 0.02050 0.00092 0.00674 0.00297 C1 1 0.616108 0.723441 0.625519 11.00000 0.02752 0.02094 = 0.02375 -0.00335 0.00710 -0.00280 AFIX 43 H1 2 0.602570 0.587205 0.581578 11.00000 -1.20000 AFIX 0 C2 1 0.540699 0.886435 0.644465 11.00000 0.02811 0.02131 = 0.01958 0.00006 0.00937 -0.00112 C3 1 0.694943 1.008409 0.737131 11.00000 0.03296 0.02313 = 0.03182 -0.00770 0.01213 -0.00647 AFIX 43 H3 2 0.750466 1.097967 0.783924 11.00000 -1.20000 AFIX 0 C4 1 0.886532 0.768919 0.571784 11.00000 0.03308 0.03729 = 0.02877 0.00353 0.01548 0.00247 HKLF 4 REM mj20105_0m_a.res in P2(1)/c REM R1 = 0.0589 for 1513 Fo > 4sig(Fo) and 0.0603 for all 1595 data REM 136 parameters refined using 0 restraints END WGHT 0.0986 0.2799 REM Highest difference peak 0.644, deepest hole -0.835, 1-sigma level 0.163 Q1 1 0.8572 0.7214 0.6291 11.00000 0.05 0.64 Q2 1 0.8966 0.7511 0.8672 11.00000 0.05 0.53 Q3 1 0.8010 0.7293 0.3735 11.00000 0.05 0.49 Q4 1 0.3981 1.0479 0.7154 11.00000 0.05 0.43 Q5 1 0.7175 0.7719 0.7981 11.00000 0.05 0.37 Q6 1 0.6469 0.7798 0.5148 11.00000 0.05 0.37 Q7 1 0.6130 0.3158 0.6183 11.00000 0.05 0.37 Q8 1 0.6698 0.8067 0.5340 11.00000 0.05 0.36 Q9 1 0.4192 0.7584 0.4326 11.00000 0.05 0.34 Q10 1 1.0350 0.6570 0.7158 11.00000 0.05 0.33 Q11 1 1.0075 0.7509 0.6632 11.00000 0.05 0.33 Q12 1 0.2806 1.0939 0.7057 11.00000 0.05 0.33 Q13 1 0.8979 1.0111 0.6398 11.00000 0.05 0.33 Q14 1 0.7977 0.6078 0.5685 11.00000 0.05 0.31 Q15 1 1.0233 0.5890 0.6729 11.00000 0.05 0.30 Q16 1 0.6190 0.6947 0.4809 11.00000 0.05 0.28 Q17 1 0.8054 1.3701 0.8980 11.00000 0.05 0.27 Q18 1 0.6173 1.1106 0.5991 11.00000 0.05 0.27 Q19 1 0.4727 0.8119 0.4643 11.00000 0.05 0.27 Q20 1 0.5589 0.7599 0.7389 11.00000 0.05 0.27 ; _shelx_res_checksum 96667 _olex2_submission_special_instructions 'No special instructions were received' 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 S1 S 0.84372(4) 0.67546(10) 0.69869(4) 0.0256(3) Uani 1 1 d . . . . . F1 F 0.99249(14) 0.7074(3) 0.57690(14) 0.0510(5) Uani 1 1 d . . . . . F2 F 0.82199(17) 0.6663(4) 0.48903(13) 0.0532(5) Uani 1 1 d . . . . . F3 F 0.87653(17) 0.9956(3) 0.56044(16) 0.0530(5) Uani 1 1 d . . . . . O1 O 0.82672(15) 0.4322(3) 0.69097(16) 0.0407(5) Uani 1 1 d . . . . . O2 O 0.91564(16) 0.7881(4) 0.78591(14) 0.0428(5) Uani 1 1 d . . . . . O3 O 0.38572(16) 0.7293(4) 0.53542(15) 0.0398(5) Uani 1 1 d . . . . . O4 O 0.36232(16) 1.0319(3) 0.63278(16) 0.0409(5) Uani 1 1 d . . . . . N1 N 0.71755(16) 0.8034(3) 0.68562(15) 0.0232(4) Uani 1 1 d . . . . . N2 N 0.58889(18) 1.0618(3) 0.71334(16) 0.0295(5) Uani 1 1 d . . . . . N3 N 0.42163(17) 0.8830(4) 0.60149(14) 0.0275(5) Uani 1 1 d . . . . . C1 C 0.61611(19) 0.7234(4) 0.62552(16) 0.0238(5) Uani 1 1 d . . . . . H1 H 0.602570 0.587205 0.581578 0.029 Uiso 1 1 calc R . . . . C2 C 0.54070(18) 0.8864(4) 0.64447(16) 0.0224(5) Uani 1 1 d . . . . . C3 C 0.6949(2) 1.0084(4) 0.73713(19) 0.0285(5) Uani 1 1 d . . . . . H3 H 0.750466 1.097967 0.783924 0.034 Uiso 1 1 calc R . . . . C4 C 0.8865(2) 0.7689(5) 0.57178(18) 0.0318(5) Uani 1 1 d . . . . . 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 S1 0.0245(4) 0.0289(4) 0.0248(4) 0.00361(18) 0.0085(2) -0.00012(18) F1 0.0352(9) 0.0702(12) 0.0547(10) 0.0144(8) 0.0267(8) 0.0139(8) F2 0.0599(12) 0.0722(14) 0.0283(9) -0.0078(7) 0.0110(8) 0.0018(9) F3 0.0680(12) 0.0357(10) 0.0647(11) 0.0169(8) 0.0362(10) 0.0017(8) O1 0.0366(10) 0.0263(11) 0.0627(13) 0.0104(8) 0.0183(9) 0.0053(7) O2 0.0308(10) 0.0673(14) 0.0293(9) -0.0059(8) 0.0037(8) -0.0023(9) O3 0.0365(10) 0.0485(12) 0.0321(9) -0.0121(8) 0.0005(7) 0.0016(8) O4 0.0358(10) 0.0444(11) 0.0422(10) -0.0061(8) 0.0065(8) 0.0162(8) N1 0.0251(10) 0.0218(9) 0.0244(9) -0.0020(7) 0.0088(7) -0.0023(7) N2 0.0356(11) 0.0218(10) 0.0334(10) -0.0064(7) 0.0127(8) -0.0020(8) N3 0.0320(10) 0.0305(10) 0.0205(9) 0.0009(7) 0.0067(7) 0.0030(8) C1 0.0275(11) 0.0209(11) 0.0237(10) -0.0034(8) 0.0071(8) -0.0028(8) C2 0.0281(11) 0.0213(10) 0.0196(9) 0.0001(8) 0.0094(8) -0.0011(8) C3 0.0330(12) 0.0231(11) 0.0318(11) -0.0077(9) 0.0121(10) -0.0065(9) C4 0.0331(13) 0.0373(14) 0.0288(11) 0.0035(10) 0.0155(10) 0.0025(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0148 0.0070 '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 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2924 0.4247 '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 S1 O2 124.35(12) . . ? O1 S1 N1 108.01(10) . . ? O1 S1 C4 106.84(12) . . ? O2 S1 N1 106.73(11) . . ? O2 S1 C4 107.47(12) . . ? N1 S1 C4 101.04(10) . . ? C1 N1 S1 127.03(16) . . ? C1 N1 C3 107.34(19) . . ? C3 N1 S1 125.60(16) . . ? C3 N2 C2 104.51(18) . . ? O3 N3 C2 117.36(19) . . ? O4 N3 O3 124.2(2) . . ? O4 N3 C2 118.4(2) . . ? N1 C1 H1 128.3 . . ? C2 C1 N1 103.33(19) . . ? C2 C1 H1 128.3 . . ? N2 C2 N3 121.1(2) . . ? C1 C2 N2 113.3(2) . . ? C1 C2 N3 125.7(2) . . ? N1 C3 H3 124.2 . . ? N2 C3 N1 111.5(2) . . ? N2 C3 H3 124.2 . . ? F1 C4 S1 108.24(16) . . ? F2 C4 S1 109.15(18) . . ? F2 C4 F1 110.0(2) . . ? F2 C4 F3 109.4(2) . . ? F3 C4 S1 110.25(17) . . ? F3 C4 F1 109.8(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 S1 O1 1.408(2) . ? S1 O2 1.4116(19) . ? S1 N1 1.669(2) . ? S1 C4 1.842(2) . ? F1 C4 1.316(3) . ? F2 C4 1.308(3) . ? F3 C4 1.308(3) . ? O3 N3 1.227(3) . ? O4 N3 1.225(3) . ? N1 C1 1.384(3) . ? N1 C3 1.392(3) . ? N2 C2 1.377(3) . ? N2 C3 1.293(3) . ? N3 C2 1.434(3) . ? C1 H1 0.9500 . ? C1 C2 1.356(3) . ? C3 H3 0.9500 . ?