#------------------------------------------------------------------------------ #$Date: 2019-11-17 07:44:38 +0200 (Sun, 17 Nov 2019) $ #$Revision: 228722 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/78/1547872.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_1547872 loop_ _publ_author_name 'Wei, Peng' 'Yuan, Wei' 'Xue, Fengfeng' 'Zhou, Wei' 'Li, Ruohan' 'Zhang, Datong' 'Yi, Tao' _publ_section_title ; Deformylation reaction-based probe for in vivo imaging of HOCl. ; _journal_issue 2 _journal_name_full 'Chemical science' _journal_page_first 495 _journal_page_last 501 _journal_paper_doi 10.1039/c7sc03784h _journal_volume 9 _journal_year 2018 _chemical_formula_sum 'C17 H19 N3 O S' _chemical_formula_weight 313.41 _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_creation_method SHELXL-2013 _audit_update_record ; 2017-06-13 deposited with the CCDC. 2017-11-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.741(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.166(4) _cell_length_b 8.073(2) _cell_length_c 12.176(3) _cell_measurement_reflns_used 2093 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.53 _cell_measurement_theta_min 2.56 _cell_volume 1566.2(7) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_unetI/netI 0.0535 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 10950 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.411 _diffrn_reflns_theta_min 2.557 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_correction_T_min 0.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.329 _exptl_crystal_description stick _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.191 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 3538 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0433 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.2566P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1016 _refine_ls_wR_factor_ref 0.1188 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2280 _reflns_number_total 3538 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc03784h5.cif _cod_data_source_block mo_51231ba _cod_depositor_comments 'Adding full bibliography for 1547871--1547872.cif.' _cod_original_cell_volume 1566.1(7) _cod_database_code 1547872 _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 0.905 _shelx_estimated_absorpt_t_max 0.992 _shelxl_version_number 2013-2 _shelx_res_file ; TITL mo_51231ba in P2(1)/c CELL 0.71073 16.1661 8.0726 12.1761 90.000 99.741 90.000 ZERR 4.00 0.0040 0.0020 0.0030 0.000 0.004 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 68 76 12 4 4 OMIT 7 0 4 OMIT 10 0 4 L.S. 4 ACTA BOND FMAP 2 PLAN 1 CONF SIZE 0.04 0.08 0.48 TEMP 23.000 WGHT 0.051000 0.256600 FVAR 0.23068 MOLE 1 S1 5 0.297452 0.194403 0.466235 11.00000 0.04744 0.06360 = 0.03049 -0.00551 0.01029 -0.01001 N1 3 0.265996 0.362673 0.673528 11.00000 0.04818 0.04276 = 0.03851 -0.00260 0.01227 0.00639 N2 3 0.605415 0.331224 0.621210 11.00000 0.04493 0.07081 = 0.06361 -0.00688 0.01032 -0.01484 N3 3 0.058834 -0.185046 0.536483 11.00000 0.05082 0.06235 = 0.05931 0.00078 0.01113 -0.01291 O1 4 0.163795 0.528559 0.723784 11.00000 0.08740 0.07998 = 0.09135 -0.00091 0.03065 0.03794 C1 1 0.375438 0.276729 0.570678 11.00000 0.04593 0.03765 = 0.03189 0.00058 0.00904 -0.00491 C2 1 0.352831 0.353171 0.663496 11.00000 0.04837 0.03650 = 0.03490 0.00030 0.01135 -0.00162 C3 1 0.415736 0.420339 0.741703 11.00000 0.06404 0.04520 = 0.03505 -0.00421 0.01173 -0.00953 AFIX 43 H3 2 0.402021 0.468428 0.805669 11.00000 -1.20000 AFIX 0 C4 1 0.497933 0.417648 0.727071 11.00000 0.05723 0.05234 = 0.04135 -0.00250 0.00207 -0.01666 AFIX 43 H4 2 0.538459 0.468002 0.779845 11.00000 -1.20000 AFIX 0 C5 1 0.522332 0.340770 0.634421 11.00000 0.04730 0.04264 = 0.04595 0.00324 0.00859 -0.01075 C6 1 0.458672 0.268831 0.556774 11.00000 0.04804 0.04241 = 0.03853 -0.00229 0.01195 -0.00500 AFIX 43 H6 2 0.472479 0.214867 0.494858 11.00000 -1.20000 AFIX 0 C7 1 0.625616 0.278200 0.515881 11.00000 0.04735 0.06974 = 0.07374 0.00446 0.01921 0.00194 AFIX 137 H7A 2 0.612650 0.162676 0.505084 11.00000 -1.50000 H7B 2 0.684338 0.295423 0.515598 11.00000 -1.50000 H7C 2 0.593321 0.341176 0.456790 11.00000 -1.50000 AFIX 0 C8 1 0.667773 0.424161 0.695169 11.00000 0.05468 0.06586 = 0.08645 0.00358 -0.00088 -0.01802 AFIX 137 H8A 2 0.654419 0.540024 0.688964 11.00000 -1.50000 H8B 2 0.722006 0.405803 0.675230 11.00000 -1.50000 H8C 2 0.668373 0.388477 0.770510 11.00000 -1.50000 AFIX 0 C9 1 0.224028 0.130212 0.549354 11.00000 0.03542 0.04686 = 0.03167 0.00342 0.00602 0.00521 C10 1 0.214108 0.219856 0.643462 11.00000 0.03487 0.05081 = 0.03211 0.00233 0.00384 0.00727 C11 1 0.155384 0.165320 0.705651 11.00000 0.03769 0.06879 = 0.03624 -0.00125 0.01074 0.00880 AFIX 43 H11 2 0.149697 0.220349 0.771061 11.00000 -1.20000 AFIX 0 C12 1 0.105131 0.030379 0.671950 11.00000 0.03787 0.07329 = 0.04594 0.00758 0.01286 0.00058 AFIX 43 H12 2 0.065686 -0.002896 0.714885 11.00000 -1.20000 AFIX 0 C13 1 0.111882 -0.058039 0.574707 11.00000 0.03306 0.05429 = 0.04497 0.00796 0.00162 0.00082 C14 1 0.175334 -0.006769 0.515878 11.00000 0.03828 0.05085 = 0.03738 -0.00128 0.00476 0.00341 AFIX 43 H14 2 0.184488 -0.066172 0.453597 11.00000 -1.20000 AFIX 0 C15 1 -0.001840 -0.245371 0.601873 11.00000 0.04796 0.07554 = 0.08057 0.01730 0.01304 -0.00992 AFIX 137 H15A 2 0.026986 -0.298025 0.668138 11.00000 -1.50000 H15B 2 -0.038406 -0.323904 0.558790 11.00000 -1.50000 H15C 2 -0.034319 -0.154171 0.622037 11.00000 -1.50000 AFIX 0 C16 1 0.074114 -0.287071 0.445126 11.00000 0.07517 0.07024 = 0.07896 -0.01336 0.01372 -0.02120 AFIX 137 H16A 2 0.083436 -0.217846 0.384284 11.00000 -1.50000 H16B 2 0.026337 -0.356853 0.421462 11.00000 -1.50000 H16C 2 0.122765 -0.354595 0.468671 11.00000 -1.50000 AFIX 0 C17 1 0.234534 0.507638 0.706689 11.00000 0.08239 0.05378 = 0.05258 -0.00200 0.01968 0.01732 AFIX 43 H17 2 0.270620 0.598126 0.717027 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_51231ba in P2(1)/c REM R1 = 0.0433 for 2280 Fo > 4sig(Fo) and 0.0836 for all 3538 data REM 203 parameters refined using 0 restraints END WGHT 0.0497 0.2819 REM Highest difference peak 0.191, deepest hole -0.202, 1-sigma level 0.042 Q1 1 0.3183 0.5964 0.7372 11.00000 0.05 0.19 ; _shelx_res_checksum 35441 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 S1 S 0.29745(3) 0.19440(7) 0.46623(4) 0.04675(18) Uani 1 1 d . . N1 N 0.26600(10) 0.3627(2) 0.67353(14) 0.0426(4) Uani 1 1 d . . N2 N 0.60542(11) 0.3312(3) 0.62121(17) 0.0597(5) Uani 1 1 d . . N3 N 0.05883(12) -0.1850(2) 0.53648(17) 0.0573(5) Uani 1 1 d . . O1 O 0.16379(12) 0.5286(2) 0.72378(18) 0.0844(6) Uani 1 1 d . . C1 C 0.37544(12) 0.2767(2) 0.57068(16) 0.0382(5) Uani 1 1 d . . C2 C 0.35283(12) 0.3532(2) 0.66350(16) 0.0394(5) Uani 1 1 d . . C3 C 0.41574(14) 0.4203(3) 0.74170(18) 0.0477(5) Uani 1 1 d . . H3 H 0.4020 0.4684 0.8057 0.057 Uiso 1 1 calc R U C4 C 0.49793(14) 0.4176(3) 0.72707(18) 0.0510(6) Uani 1 1 d . . H4 H 0.5385 0.4680 0.7798 0.061 Uiso 1 1 calc R U C5 C 0.52233(13) 0.3408(3) 0.63442(18) 0.0452(5) Uani 1 1 d . . C6 C 0.45867(12) 0.2688(2) 0.55677(17) 0.0425(5) Uani 1 1 d . . H6 H 0.4725 0.2149 0.4949 0.051 Uiso 1 1 calc R U C7 C 0.62562(14) 0.2782(3) 0.5159(2) 0.0626(7) Uani 1 1 d . . H7A H 0.6126 0.1627 0.5051 0.094 Uiso 1 1 calc R U H7B H 0.6843 0.2954 0.5156 0.094 Uiso 1 1 calc R U H7C H 0.5933 0.3412 0.4568 0.094 Uiso 1 1 calc R U C8 C 0.66777(15) 0.4242(3) 0.6952(2) 0.0705(8) Uani 1 1 d . . H8A H 0.6544 0.5400 0.6890 0.106 Uiso 1 1 calc R U H8B H 0.7220 0.4058 0.6752 0.106 Uiso 1 1 calc R U H8C H 0.6684 0.3885 0.7705 0.106 Uiso 1 1 calc R U C9 C 0.22403(11) 0.1302(3) 0.54935(16) 0.0379(4) Uani 1 1 d . . C10 C 0.21411(12) 0.2199(3) 0.64346(16) 0.0395(5) Uani 1 1 d . . C11 C 0.15538(12) 0.1653(3) 0.70565(17) 0.0471(5) Uani 1 1 d . . H11 H 0.1497 0.2203 0.7711 0.056 Uiso 1 1 calc R U C12 C 0.10513(12) 0.0304(3) 0.67195(19) 0.0517(6) Uani 1 1 d . . H12 H 0.0657 -0.0029 0.7149 0.062 Uiso 1 1 calc R U C13 C 0.11188(12) -0.0580(3) 0.57471(18) 0.0447(5) Uani 1 1 d . . C14 C 0.17533(11) -0.0068(3) 0.51588(17) 0.0424(5) Uani 1 1 d . . H14 H 0.1845 -0.0662 0.4536 0.051 Uiso 1 1 calc R U C15 C -0.00184(15) -0.2454(3) 0.6019(2) 0.0678(7) Uani 1 1 d . . H15A H 0.0270 -0.2980 0.6681 0.102 Uiso 1 1 calc R U H15B H -0.0384 -0.3239 0.5588 0.102 Uiso 1 1 calc R U H15C H -0.0343 -0.1542 0.6220 0.102 Uiso 1 1 calc R U C16 C 0.07411(17) -0.2871(3) 0.4451(3) 0.0747(8) Uani 1 1 d . . H16A H 0.0834 -0.2178 0.3843 0.112 Uiso 1 1 calc R U H16B H 0.0263 -0.3569 0.4215 0.112 Uiso 1 1 calc R U H16C H 0.1228 -0.3546 0.4687 0.112 Uiso 1 1 calc R U C17 C 0.23453(17) 0.5076(3) 0.7067(2) 0.0620(7) Uani 1 1 d . . H17 H 0.2706 0.5981 0.7170 0.074 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 S1 0.0474(3) 0.0636(4) 0.0305(3) -0.0055(3) 0.0103(2) -0.0100(3) N1 0.0482(10) 0.0428(10) 0.0385(10) -0.0026(8) 0.0123(8) 0.0064(8) N2 0.0449(10) 0.0708(14) 0.0636(13) -0.0069(11) 0.0103(9) -0.0148(9) N3 0.0508(11) 0.0624(13) 0.0593(13) 0.0008(10) 0.0111(9) -0.0129(10) O1 0.0874(13) 0.0800(14) 0.0914(15) -0.0009(11) 0.0306(11) 0.0379(11) C1 0.0459(11) 0.0377(11) 0.0319(10) 0.0006(8) 0.0090(9) -0.0049(9) C2 0.0484(11) 0.0365(11) 0.0349(11) 0.0003(9) 0.0113(9) -0.0016(9) C3 0.0640(14) 0.0452(13) 0.0350(11) -0.0042(9) 0.0117(10) -0.0095(10) C4 0.0572(13) 0.0523(14) 0.0413(13) -0.0025(10) 0.0021(10) -0.0167(11) C5 0.0473(12) 0.0426(12) 0.0460(13) 0.0032(10) 0.0086(10) -0.0107(9) C6 0.0480(11) 0.0424(12) 0.0385(11) -0.0023(9) 0.0120(9) -0.0050(9) C7 0.0474(13) 0.0697(17) 0.0737(17) 0.0045(14) 0.0192(13) 0.0019(12) C8 0.0547(14) 0.0659(17) 0.086(2) 0.0036(14) -0.0009(14) -0.0180(12) C9 0.0354(10) 0.0469(12) 0.0317(10) 0.0034(9) 0.0060(8) 0.0052(9) C10 0.0349(10) 0.0508(13) 0.0321(10) 0.0023(9) 0.0038(8) 0.0073(9) C11 0.0377(11) 0.0688(16) 0.0362(11) -0.0013(10) 0.0107(9) 0.0088(10) C12 0.0379(11) 0.0733(16) 0.0459(13) 0.0076(12) 0.0129(10) 0.0006(11) C13 0.0331(10) 0.0543(14) 0.0450(12) 0.0080(10) 0.0016(9) 0.0008(9) C14 0.0383(10) 0.0508(13) 0.0374(11) -0.0013(10) 0.0048(9) 0.0034(9) C15 0.0480(13) 0.0755(18) 0.0806(19) 0.0173(14) 0.0130(13) -0.0099(12) C16 0.0752(18) 0.0702(18) 0.079(2) -0.0134(16) 0.0137(15) -0.0212(14) C17 0.0824(18) 0.0538(15) 0.0526(15) -0.0020(12) 0.0197(13) 0.0173(13) 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' 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' S S 0.1246 0.1234 '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 C1 S1 C9 99.53(9) C17 N1 C2 119.43(19) C17 N1 C10 122.22(18) C2 N1 C10 118.30(15) C5 N2 C7 119.4(2) C5 N2 C8 119.2(2) C7 N2 C8 118.0(2) C13 N3 C16 120.85(19) C13 N3 C15 120.6(2) C16 N3 C15 117.0(2) C6 C1 C2 120.94(19) C6 C1 S1 119.04(15) C2 C1 S1 119.99(15) C3 C2 C1 118.09(19) C3 C2 N1 122.58(18) C1 C2 N1 119.32(18) C4 C3 C2 121.4(2) C3 C4 C5 121.5(2) N2 C5 C6 121.1(2) N2 C5 C4 122.0(2) C6 C5 C4 116.89(19) C1 C6 C5 121.09(19) C14 C9 C10 121.51(18) C14 C9 S1 118.19(15) C10 C9 S1 120.26(16) C11 C10 C9 118.2(2) C11 C10 N1 122.79(18) C9 C10 N1 119.02(17) C12 C11 C10 120.9(2) C11 C12 C13 121.81(19) N3 C13 C12 122.36(19) N3 C13 C14 121.1(2) C12 C13 C14 116.6(2) C9 C14 C13 120.9(2) O1 C17 N1 125.6(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.762(2) S1 C9 1.763(2) N1 C17 1.364(3) N1 C2 1.432(2) N1 C10 1.436(3) N2 C5 1.382(3) N2 C7 1.441(3) N2 C8 1.443(3) N3 C13 1.367(3) N3 C16 1.439(3) N3 C15 1.448(3) O1 C17 1.208(3) C1 C6 1.386(3) C1 C2 1.390(3) C2 C3 1.381(3) C3 C4 1.370(3) C4 C5 1.401(3) C5 C6 1.400(3) C9 C14 1.378(3) C9 C10 1.387(3) C10 C11 1.383(3) C11 C12 1.379(3) C12 C13 1.403(3) C13 C14 1.409(3) 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 C9 S1 C1 C6 148.89(17) C9 S1 C1 C2 -33.26(19) C6 C1 C2 C3 -0.3(3) S1 C1 C2 C3 -178.11(16) C6 C1 C2 N1 178.39(18) S1 C1 C2 N1 0.6(3) C17 N1 C2 C3 42.9(3) C10 N1 C2 C3 -139.7(2) C17 N1 C2 C1 -135.7(2) C10 N1 C2 C1 41.7(3) C1 C2 C3 C4 2.3(3) N1 C2 C3 C4 -176.32(19) C2 C3 C4 C5 -2.6(3) C7 N2 C5 C6 13.2(3) C8 N2 C5 C6 172.3(2) C7 N2 C5 C4 -168.8(2) C8 N2 C5 C4 -9.7(3) C3 C4 C5 N2 -177.2(2) C3 C4 C5 C6 0.8(3) C2 C1 C6 C5 -1.4(3) S1 C1 C6 C5 176.38(16) N2 C5 C6 C1 179.2(2) C4 C5 C6 C1 1.2(3) C1 S1 C9 C14 -148.45(16) C1 S1 C9 C10 33.83(18) C14 C9 C10 C11 2.0(3) S1 C9 C10 C11 179.60(15) C14 C9 C10 N1 -179.27(17) S1 C9 C10 N1 -1.6(3) C17 N1 C10 C11 -45.0(3) C2 N1 C10 C11 137.6(2) C17 N1 C10 C9 136.2(2) C2 N1 C10 C9 -41.1(3) C9 C10 C11 C12 -3.2(3) N1 C10 C11 C12 178.08(19) C10 C11 C12 C13 0.7(3) C16 N3 C13 C12 -171.8(2) C15 N3 C13 C12 -6.5(3) C16 N3 C13 C14 9.8(3) C15 N3 C13 C14 175.1(2) C11 C12 C13 N3 -175.6(2) C11 C12 C13 C14 2.9(3) C10 C9 C14 C13 1.8(3) S1 C9 C14 C13 -175.93(15) N3 C13 C14 C9 174.39(19) C12 C13 C14 C9 -4.1(3) C2 N1 C17 O1 -175.9(2) C10 N1 C17 O1 6.8(4)