# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_f _database_code_depnum_ccdc_archive 'CCDC 1475312' _audit_update_record ; 2016-04-20 deposited with the CCDC. 2018-04-30 downloaded from the CCDC. ; _audit_creation_date 2016-04-13 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133) ; _shelxl_version_number 2014/6 _chemical_name_common ? _chemical_name_systematic 'Hydroxy thiosemicarbazide derivative' _chemical_formula_moiety 'C9 H11 N3 O S' _chemical_formula_sum 'C9 H11 N3 O S' _chemical_formula_weight 209.27 _chemical_melting_point ? 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' _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. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.885(3) _cell_length_b 7.108(3) _cell_length_c 11.230(4) _cell_angle_alpha 74.336(4) _cell_angle_beta 76.662(4) _cell_angle_gamma 73.802(4) _cell_volume 500.9(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2105 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 27.477 _cell_measurement_theta_min 3.059 _shelx_estimated_absorpt_T_max 0.988 _shelx_estimated_absorpt_T_min 0.930 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6360 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0450 before and 0.0355 after correction. The Ratio of minimum to maximum transmission is 0.8530. The \l/2 correction factor is Not present. ; _exptl_absorpt_special_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 220 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_unetI/netI 0.0375 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4355 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.967 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.519 _diffrn_reflns_theta_min 1.910 _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.967 _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_source ? _diffrn_special_details ? _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1928 _reflns_number_total 2227 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection ? _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _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)' _refine_diff_density_max 0.291 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.060 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 2227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0382 _refine_ls_restrained_S_all 1.049 _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^)+(0.0552P)^2^+0.1465P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0998 _refine_ls_wR_factor_ref 0.1042 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6) 2.b X=CH2 refined with riding coordinates: N3(H3A,H3B) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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 0.28281(6) 0.26829(6) -0.06621(4) 0.02164(15) Uani 1 1 d . . . . . O1 O 0.70931(18) 0.29306(19) 0.73936(11) 0.0241(3) Uani 1 1 d . . . . . H1 H 0.5969 0.2873 0.7875 0.036 Uiso 1 1 calc GR . . . . N1 N 0.5105(2) 0.2558(2) 0.22599(12) 0.0195(3) Uani 1 1 d . . . . . N2 N 0.4945(2) 0.2211(2) 0.11301(12) 0.0205(3) Uani 1 1 d . . . . . H2 H 0.5926 0.1374 0.0748 0.025 Uiso 1 1 calc R . . . . N3 N 0.1932(2) 0.4561(2) 0.12159(13) 0.0222(3) Uani 1 1 d . . . . . H3A H 0.2199 0.4790 0.1887 0.027 Uiso 1 1 calc R . . . . H3B H 0.0795 0.5241 0.0926 0.027 Uiso 1 1 calc R . . . . C1 C 0.6927(2) 0.2221(2) 0.38535(14) 0.0166(3) Uani 1 1 d . . . . . C2 C 0.8711(2) 0.2404(2) 0.41622(15) 0.0207(4) Uani 1 1 d . . . . . H2A H 0.9933 0.2336 0.3558 0.025 Uiso 1 1 calc R . . . . C3 C 0.8727(2) 0.2682(3) 0.53316(15) 0.0220(4) Uani 1 1 d . . . . . H3 H 0.9943 0.2841 0.5516 0.026 Uiso 1 1 calc R . . . . C4 C 0.6967(2) 0.2730(2) 0.62375(14) 0.0179(3) Uani 1 1 d . . . . . C5 C 0.5172(2) 0.2562(2) 0.59510(15) 0.0191(3) Uani 1 1 d . . . . . H5 H 0.3959 0.2608 0.6563 0.023 Uiso 1 1 calc R . . . . C6 C 0.5161(2) 0.2326(2) 0.47727(15) 0.0184(3) Uani 1 1 d . . . . . H6 H 0.3922 0.2233 0.4580 0.022 Uiso 1 1 calc R . . . . C7 C 0.6869(2) 0.1914(2) 0.26109(15) 0.0177(3) Uani 1 1 d . . . . . C8 C 0.8770(2) 0.0883(3) 0.18678(16) 0.0248(4) Uani 1 1 d . . . . . H8A H 0.8686 -0.0489 0.1914 0.037 Uiso 1 1 calc GR . . . . H8B H 0.9970 0.0840 0.2212 0.037 Uiso 1 1 calc GR . . . . H8C H 0.8898 0.1622 0.0991 0.037 Uiso 1 1 calc GR . . . . C9 C 0.3238(2) 0.3198(2) 0.06451(14) 0.0177(3) 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 0.0224(2) 0.0291(3) 0.0153(2) -0.01047(17) -0.00499(15) -0.00201(17) O1 0.0240(6) 0.0334(7) 0.0175(6) -0.0124(5) -0.0050(5) -0.0030(5) N1 0.0244(7) 0.0214(7) 0.0135(7) -0.0067(5) -0.0057(5) -0.0017(6) N2 0.0223(7) 0.0249(7) 0.0139(7) -0.0098(6) -0.0044(5) 0.0015(6) N3 0.0222(7) 0.0273(8) 0.0193(7) -0.0124(6) -0.0089(5) 0.0022(6) C1 0.0203(8) 0.0148(7) 0.0139(7) -0.0030(6) -0.0034(6) -0.0024(6) C2 0.0185(8) 0.0247(9) 0.0174(8) -0.0063(7) -0.0008(6) -0.0030(7) C3 0.0197(8) 0.0267(9) 0.0219(9) -0.0082(7) -0.0060(6) -0.0045(7) C4 0.0237(8) 0.0157(7) 0.0142(8) -0.0047(6) -0.0063(6) -0.0006(6) C5 0.0189(8) 0.0204(8) 0.0173(8) -0.0060(6) -0.0011(6) -0.0031(6) C6 0.0195(8) 0.0188(8) 0.0176(8) -0.0044(6) -0.0049(6) -0.0037(6) C7 0.0215(8) 0.0167(8) 0.0148(8) -0.0028(6) -0.0036(6) -0.0043(6) C8 0.0207(8) 0.0355(10) 0.0207(8) -0.0137(7) -0.0023(6) -0.0043(7) C9 0.0195(8) 0.0197(8) 0.0144(7) -0.0039(6) -0.0028(6) -0.0050(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C9 1.7053(17) . ? O1 H1 0.8400 . ? O1 C4 1.3683(19) . ? N1 N2 1.3897(19) . ? N1 C7 1.286(2) . ? N2 H2 0.8800 . ? N2 C9 1.341(2) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N3 C9 1.320(2) . ? C1 C2 1.399(2) . ? C1 C6 1.400(2) . ? C1 C7 1.480(2) . ? C2 H2A 0.9500 . ? C2 C3 1.383(2) . ? C3 H3 0.9500 . ? C3 C4 1.390(2) . ? C4 C5 1.390(2) . ? C5 H5 0.9500 . ? C5 C6 1.380(2) . ? C6 H6 0.9500 . ? C7 C8 1.496(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C4 O1 H1 109.5 . . ? C7 N1 N2 117.52(14) . . ? N1 N2 H2 121.3 . . ? C9 N2 N1 117.48(13) . . ? C9 N2 H2 121.3 . . ? H3A N3 H3B 120.0 . . ? C9 N3 H3A 120.0 . . ? C9 N3 H3B 120.0 . . ? C2 C1 C6 117.54(14) . . ? C2 C1 C7 122.26(14) . . ? C6 C1 C7 120.20(14) . . ? C1 C2 H2A 119.4 . . ? C3 C2 C1 121.15(14) . . ? C3 C2 H2A 119.4 . . ? C2 C3 H3 119.9 . . ? C2 C3 C4 120.14(15) . . ? C4 C3 H3 119.9 . . ? O1 C4 C3 117.62(14) . . ? O1 C4 C5 122.62(14) . . ? C3 C4 C5 119.76(15) . . ? C4 C5 H5 120.2 . . ? C6 C5 C4 119.63(14) . . ? C6 C5 H5 120.2 . . ? C1 C6 H6 119.1 . . ? C5 C6 C1 121.75(15) . . ? C5 C6 H6 119.1 . . ? N1 C7 C1 115.28(14) . . ? N1 C7 C8 124.54(15) . . ? C1 C7 C8 120.18(14) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 S1 120.14(12) . . ? N3 C9 S1 122.56(12) . . ? N3 C9 N2 117.30(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 S1 0.84 2.41 3.2470(16) 177.3 1_556 N2 H2 S1 0.88 2.79 3.5165(19) 140.6 2_655 N3 H3A O1 0.88 2.20 2.9533(19) 143.2 2_666 N3 H3B S1 0.88 2.56 3.4157(18) 165.3 2_565 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 O1 C4 C5 C6 -178.82(14) . . . . ? N1 N2 C9 S1 -174.12(11) . . . . ? N1 N2 C9 N3 6.2(2) . . . . ? N2 N1 C7 C1 -176.66(12) . . . . ? N2 N1 C7 C8 2.2(2) . . . . ? C1 C2 C3 C4 1.8(2) . . . . ? C2 C1 C6 C5 -1.3(2) . . . . ? C2 C1 C7 N1 -153.10(16) . . . . ? C2 C1 C7 C8 28.0(2) . . . . ? C2 C3 C4 O1 177.48(14) . . . . ? C2 C3 C4 C5 -2.1(2) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C4 C5 C6 C1 1.0(2) . . . . ? C6 C1 C2 C3 -0.1(2) . . . . ? C6 C1 C7 N1 27.2(2) . . . . ? C6 C1 C7 C8 -151.64(16) . . . . ? C7 N1 N2 C9 -167.55(15) . . . . ? C7 C1 C2 C3 -179.77(15) . . . . ? C7 C1 C6 C5 178.39(14) . . . . ? _shelx_res_file ; TITL f_a.res in P-1 REM Old TITL F in P-1 #2 REM SHELXT solution in P-1 REM R1 0.106, Rweak 0.006, Alpha 0.042, Orientation as input REM Formula found by SHELXT: C9 N2 O2 S CELL 0.71073 6.8846 7.1081 11.2302 74.336 76.662 73.802 ZERR 2 0.0027 0.0028 0.0044 0.004 0.004 0.004 LATT 1 SFAC C H N O S UNIT 18 22 6 2 2 EQIV $1 +X,+Y,1+Z EQIV $2 1-X,-Y,-Z EQIV $3 1-X,1-Y,1-Z EQIV $4 -X,1-Y,-Z L.S. 10 PLAN 20 SIZE 0.04 0.19 0.25 TEMP -123.15 HTAB O1 S1_$1 HTAB N2 S1_$2 HTAB N3 O1_$3 HTAB N3 S1_$4 BOND $H acta more -1 wpdb -1 htab conf fmap 2 REM REM REM WGHT 0.055200 0.146500 FVAR 0.98690 S1 5 0.282809 0.268290 -0.066209 11.00000 0.02243 0.02907 = 0.01526 -0.01047 -0.00499 -0.00201 O1 4 0.709306 0.293063 0.739355 11.00000 0.02404 0.03343 = 0.01746 -0.01236 -0.00498 -0.00303 AFIX 147 H1 2 0.596916 0.287328 0.787530 11.00000 -1.50000 AFIX 0 N1 3 0.510467 0.255778 0.225987 11.00000 0.02440 0.02136 = 0.01348 -0.00668 -0.00569 -0.00168 N2 3 0.494472 0.221056 0.113013 11.00000 0.02229 0.02491 = 0.01393 -0.00982 -0.00445 0.00149 AFIX 43 H2 2 0.592615 0.137426 0.074754 11.00000 -1.20000 AFIX 0 N3 3 0.193247 0.456100 0.121594 11.00000 0.02220 0.02726 = 0.01929 -0.01240 -0.00885 0.00219 AFIX 93 H3A 2 0.219906 0.479021 0.188670 11.00000 -1.20000 H3B 2 0.079502 0.524070 0.092586 11.00000 -1.20000 AFIX 0 C1 1 0.692657 0.222063 0.385352 11.00000 0.02031 0.01483 = 0.01387 -0.00304 -0.00337 -0.00240 C2 1 0.871085 0.240376 0.416223 11.00000 0.01853 0.02470 = 0.01745 -0.00627 -0.00081 -0.00299 AFIX 43 H2A 2 0.993320 0.233564 0.355801 11.00000 -1.20000 AFIX 0 C3 1 0.872664 0.268224 0.533158 11.00000 0.01974 0.02672 = 0.02189 -0.00820 -0.00599 -0.00452 AFIX 43 H3 2 0.994306 0.284123 0.551604 11.00000 -1.20000 AFIX 0 C4 1 0.696670 0.273001 0.623755 11.00000 0.02372 0.01568 = 0.01419 -0.00474 -0.00632 -0.00061 C5 1 0.517166 0.256164 0.595099 11.00000 0.01886 0.02039 = 0.01726 -0.00598 -0.00110 -0.00313 AFIX 43 H5 2 0.395908 0.260834 0.656297 11.00000 -1.20000 AFIX 0 C6 1 0.516073 0.232629 0.477267 11.00000 0.01951 0.01885 = 0.01760 -0.00440 -0.00488 -0.00375 AFIX 43 H6 2 0.392230 0.223345 0.457982 11.00000 -1.20000 AFIX 0 C7 1 0.686911 0.191409 0.261095 11.00000 0.02146 0.01667 = 0.01483 -0.00275 -0.00358 -0.00425 C8 1 0.876951 0.088289 0.186785 11.00000 0.02075 0.03550 = 0.02073 -0.01367 -0.00235 -0.00426 AFIX 137 H8A 2 0.868563 -0.048936 0.191359 11.00000 -1.50000 H8B 2 0.996977 0.084003 0.221225 11.00000 -1.50000 H8C 2 0.889834 0.162232 0.099079 11.00000 -1.50000 AFIX 0 C9 1 0.323838 0.319805 0.064508 11.00000 0.01951 0.01969 = 0.01437 -0.00391 -0.00276 -0.00504 HKLF 4 REM f_a.res in P-1 REM R1 = 0.0382 for 1928 Fo > 4sig(Fo) and 0.0439 for all 2227 data REM 129 parameters refined using 0 restraints END WGHT 0.0552 0.1465 REM Instructions for potential hydrogen bonds HTAB O1 S1_$1 HTAB N2 S1_$2 HTAB N3 O1_$3 HTAB N3 S1_$4 HTAB C8 S1_$2 REM Highest difference peak 0.291, deepest hole -0.287, 1-sigma level 0.060 Q1 1 0.5852 0.3111 0.5953 11.00000 0.05 0.29 Q2 1 0.5299 0.0958 0.0980 11.00000 0.05 0.29 Q3 1 0.1538 0.3640 -0.0787 11.00000 0.05 0.27 Q4 1 0.6176 0.1818 0.4365 11.00000 0.05 0.27 Q5 1 0.3773 0.3655 -0.0704 11.00000 0.05 0.27 Q6 1 0.6254 0.2023 0.6161 11.00000 0.05 0.27 Q7 1 0.8693 0.0519 0.1132 11.00000 0.05 0.26 Q8 1 0.7590 0.2665 0.3961 11.00000 0.05 0.24 Q9 1 0.7811 0.1989 0.4057 11.00000 0.05 0.24 Q10 1 0.6011 0.2595 0.4196 11.00000 0.05 0.24 Q11 1 0.5318 0.2218 0.5399 11.00000 0.05 0.23 Q12 1 0.1952 0.1841 -0.0553 11.00000 0.05 0.23 Q13 1 0.7635 0.3217 0.5680 11.00000 0.05 0.22 Q14 1 0.9670 -0.0173 0.2244 11.00000 0.05 0.22 Q15 1 1.0282 0.1198 0.1552 11.00000 0.05 0.21 Q16 1 0.7806 0.1293 0.2244 11.00000 0.05 0.21 Q17 1 0.3867 0.2492 0.1048 11.00000 0.05 0.21 Q18 1 0.6029 0.1670 0.2567 11.00000 0.05 0.20 Q19 1 0.6873 0.2259 0.3191 11.00000 0.05 0.20 Q20 1 0.4126 0.1665 -0.0569 11.00000 0.05 0.20 ; _shelx_res_checksum 10203 _olex2_submission_special_instructions 'No special instructions were received' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _solvent_exptl_crystal_recrystallization_method Acetonitrile