#------------------------------------------------------------------------------ #$Date: 2020-08-01 03:58:32 +0300 (Sat, 01 Aug 2020) $ #$Revision: 254716 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/87/1558722.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_1558722 loop_ _publ_author_name 'Berton, Cesare' 'Busiello, Daniel Maria' 'Zamuner, Stefano' 'Solari, Euro' 'Scopelliti, Rosario' 'Fadaei-Tirani, Farzaneh' 'Severin, Kay' 'Pezzato, Cristian' _publ_section_title ; Thermodynamics and kinetics of protonated merocyanine photoacids in water ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC03152F _journal_year 2020 _chemical_formula_moiety 'C20 H21 N O4 S' _chemical_formula_sum 'C20 H21 N O4 S' _chemical_formula_weight 371.44 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2019-10-08 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.10.03 svn.r3662 for OlexSys, GUI svn.r5953) ; _audit_update_record ; 2020-05-22 deposited with the CCDC. 2020-07-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.2199(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.33916(6) _cell_length_b 19.51555(15) _cell_length_c 11.56961(9) _cell_measurement_reflns_used 13067 _cell_measurement_temperature 140.00(10) _cell_measurement_theta_max 75.8260 _cell_measurement_theta_min 4.4980 _cell_volume 1840.22(2) _computing_cell_refinement 'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 140.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2817 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.994 _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 -115.00 -72.00 1.00 2.00 -- -40.91-153.00 28.00 43 2 \w -115.00 -32.00 1.00 2.00 -- -40.91 -38.00 -60.00 83 3 \w -73.00 33.00 1.00 2.00 -- -40.91 19.00 120.00 106 4 \w 70.00 97.00 1.00 2.00 -- 40.91-125.00 -90.00 27 5 \w -19.00 71.00 1.00 2.00 -- 40.91 -77.00-150.00 90 6 \w 44.00 83.00 1.00 2.00 -- 40.91-125.00 90.00 39 7 \w 62.00 87.00 1.00 8.00 -- 112.00 178.00 90.00 25 8 \w 55.00 109.00 1.00 8.00 -- 112.00-111.00 120.00 54 9 \w 45.00 74.00 1.00 8.00 -- 112.00 -45.00 90.00 29 10 \w 86.00 174.00 1.00 8.00 -- 112.00 30.00 -30.00 88 11 \w 36.00 69.00 1.00 8.00 -- 112.00-111.00 30.00 33 12 \w 95.00 127.00 1.00 8.00 -- 112.00 45.00 30.00 32 13 \w 131.00 177.00 1.00 8.00 -- 112.00 45.00 30.00 46 14 \w 30.00 107.00 1.00 8.00 -- 112.00 -94.00-120.00 77 15 \w 84.00 111.00 1.00 8.00 -- 112.00 30.00 120.00 27 16 \w 69.00 95.00 1.00 8.00 -- 112.00 -94.00 150.00 26 17 \w 74.00 109.00 1.00 8.00 -- 112.00-111.00 -30.00 35 18 \w 37.00 109.00 1.00 8.00 -- 112.00-111.00-150.00 72 19 \w 55.00 104.00 1.00 8.00 -- 112.00 -94.00 30.00 49 20 \w 112.00 139.00 1.00 8.00 -- 112.00 178.00 90.00 27 21 \w 129.00 155.00 1.00 8.00 -- 112.00 30.00 120.00 26 22 \w 113.00 164.00 1.00 8.00 -- 112.00 111.00 -30.00 51 23 \w 119.00 178.00 1.00 8.00 -- 112.00 77.00-120.00 59 24 \w 84.00 109.00 1.00 8.00 -- 112.00-111.00 30.00 25 25 \w 88.00 140.00 1.00 8.00 -- 112.00 45.00 60.00 52 26 \w 146.00 175.00 1.00 8.00 -- 112.00 45.00 60.00 29 27 \w 60.00 112.00 1.00 8.00 -- 112.00 -61.00-120.00 52 28 \w 63.00 108.00 1.00 8.00 -- 112.00-111.00 150.00 45 29 \w 77.00 108.00 1.00 8.00 -- 112.00-111.00-120.00 31 30 \w 35.00 68.00 1.00 8.00 -- 112.00 -94.00-180.00 33 31 \w 42.00 132.00 1.00 8.00 -- 112.00 -45.00-150.00 90 32 \w 108.00 173.00 1.00 8.00 -- 112.00 111.00-180.00 65 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0738869000 _diffrn_orient_matrix_UB_12 0.0518416000 _diffrn_orient_matrix_UB_13 -0.0971480000 _diffrn_orient_matrix_UB_21 0.0393556000 _diffrn_orient_matrix_UB_22 0.0588598000 _diffrn_orient_matrix_UB_23 0.0903161000 _diffrn_orient_matrix_UB_31 0.1694824000 _diffrn_orient_matrix_UB_32 0.0089550000 _diffrn_orient_matrix_UB_33 -0.0310974000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_unetI/netI 0.0098 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 17018 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.101 _diffrn_reflns_theta_min 4.519 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.776 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.544 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on Gaussian integration over a multifaceted crystal model. Empirical absorption correction using spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm ; _exptl_crystal_colour 'clear intense orange' _exptl_crystal_density_diffrn 1.341 _exptl_crystal_description prism _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.602 _exptl_crystal_size_mid 0.153 _exptl_crystal_size_min 0.098 _refine_diff_density_max 0.382 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef 0.00161(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 320 _refine_ls_number_reflns 3828 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0298 _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^)+(0.0378P)^2^+0.8482P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.0769 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3742 _reflns_number_total 3828 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc03152f2.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Gaussian' was changed to 'gaussian' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 1840.21(2) _cod_database_code 1558722 _shelx_shelxl_version_number 2018/3 _audit_contact_author 'Farzaneh Fadaei Tirani' _chemical_oxdiff_formula 'C20 H21 N1 O4 S1' _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 0.845 _shelx_estimated_absorpt_t_min 0.414 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _olex2_refinement_description ; ; _shelx_res_file ; TITL cp32.res in P2(1)/n cp32.res created by SHELXL-2018/3 at 13:36:17 on 08-Oct-2019 CELL 1.54184 8.339162 19.515549 11.569608 90 102.2199 90 ZERR 4 0.000059 0.000147 0.000094 0 0.0008 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 80 84 4 16 4 EQIV $1 0.5-X,-0.5+Y,1.5-Z L.S. 20 PLAN 1 SIZE 0.602 0.153 0.098 TEMP -133.15 CONF HTAB O1 O3_$1 BOND $H fmap 2 acta MORE -1 OMIT -1 7 2 REM REM REM WGHT 0.037800 0.848200 EXTI 0.001609 FVAR 0.61119 S1 5 0.521884 0.571207 0.720993 11.00000 0.01471 0.01633 = 0.01994 -0.00285 0.00142 0.00253 O1 4 0.191867 0.238366 0.734675 11.00000 0.02135 0.02039 = 0.03526 0.00999 -0.00350 -0.00633 H1 2 0.122016 0.206721 0.739678 11.00000 0.04440 O2 4 0.501882 0.528042 0.818236 11.00000 0.02359 0.02772 = 0.02844 0.00053 0.01117 -0.00174 O3 4 0.520610 0.644375 0.748703 11.00000 0.02446 0.01836 = 0.04095 -0.00625 0.00554 0.00499 O4 4 0.414969 0.553520 0.608904 11.00000 0.02464 0.03421 = 0.02679 -0.00705 -0.00702 0.00756 N1 3 0.778772 0.434726 0.745336 11.00000 0.01335 0.01417 = 0.01642 -0.00021 0.00250 0.00068 C1 1 0.667383 0.390494 0.764848 11.00000 0.01643 0.01277 = 0.01797 -0.00122 0.00471 0.00077 C2 1 0.931270 0.425884 0.826703 11.00000 0.01423 0.01716 = 0.01643 -0.00187 0.00212 0.00216 C3 1 1.076513 0.461576 0.832117 11.00000 0.01683 0.02004 = 0.02256 -0.00146 0.00498 -0.00098 H3 2 1.087423 0.498610 0.779440 11.00000 0.02298 C4 1 1.210795 0.440074 0.917570 11.00000 0.01482 0.02630 = 0.02635 -0.00717 0.00290 -0.00098 H4 2 1.313794 0.465188 0.923766 11.00000 0.02752 C5 1 1.197129 0.385777 0.992726 11.00000 0.01748 0.02875 = 0.02249 -0.00347 -0.00183 0.00510 H5 2 1.291565 0.371654 1.050215 11.00000 0.02724 C6 1 1.048795 0.351557 0.986465 11.00000 0.02166 0.02449 = 0.02115 0.00319 0.00152 0.00417 H6 2 1.039163 0.313196 1.038790 11.00000 0.02654 C7 1 0.914290 0.372545 0.901813 11.00000 0.01603 0.01801 = 0.01865 -0.00059 0.00350 0.00131 C8 1 0.738975 0.347055 0.873400 11.00000 0.01603 0.01564 = 0.01937 0.00246 0.00309 0.00067 C9 1 0.505678 0.388518 0.693116 11.00000 0.01682 0.01622 = 0.02062 0.00094 0.00162 -0.00015 H9 2 0.482910 0.420153 0.630459 11.00000 0.02181 C10 1 0.386916 0.346248 0.713463 11.00000 0.01756 0.01597 = 0.02052 -0.00040 0.00227 0.00004 H10 2 0.411150 0.313083 0.778150 11.00000 0.02193 C11 1 0.220065 0.344396 0.644978 11.00000 0.01546 0.01677 = 0.01796 -0.00168 0.00365 -0.00105 C12 1 0.121946 0.287541 0.659132 11.00000 0.01809 0.01682 = 0.01992 -0.00006 0.00362 -0.00022 C13 1 -0.039485 0.283414 0.593611 11.00000 0.01710 0.02086 = 0.02508 -0.00225 0.00407 -0.00427 H13 2 -0.103970 0.244871 0.604166 11.00000 0.02677 C14 1 -0.103145 0.335209 0.516019 11.00000 0.01493 0.02814 = 0.02199 -0.00275 0.00093 0.00045 H14 2 -0.211319 0.332224 0.471139 11.00000 0.03241 C15 1 -0.008048 0.392420 0.502617 11.00000 0.02022 0.02368 = 0.01998 0.00295 0.00382 0.00401 H15 2 -0.055938 0.427563 0.447481 11.00000 0.02552 C16 1 0.151322 0.396912 0.566938 11.00000 0.01915 0.01827 = 0.02084 0.00102 0.00599 -0.00064 H16 2 0.213504 0.438590 0.562017 11.00000 0.02332 C17 1 0.758482 0.488314 0.654261 11.00000 0.01631 0.01495 = 0.01602 0.00156 0.00465 0.00016 H17A 2 0.671852 0.475875 0.589290 11.00000 0.01755 H17B 2 0.862303 0.489677 0.626614 11.00000 0.01615 C18 1 0.727108 0.558653 0.701947 11.00000 0.01715 0.01457 = 0.02176 0.00058 0.00611 -0.00053 H18A 2 0.799725 0.567770 0.778863 11.00000 0.02463 H18B 2 0.744288 0.593871 0.647648 11.00000 0.02502 C19 1 0.654117 0.367101 0.975246 11.00000 0.02226 0.02751 = 0.02136 0.00122 0.00724 0.00066 H19A 2 0.541441 0.350851 0.958027 11.00000 0.02570 H19B 2 0.714792 0.348071 1.050263 11.00000 0.03623 H19C 2 0.651693 0.416460 0.984332 11.00000 0.03493 C20 1 0.731641 0.269303 0.851291 11.00000 0.02413 0.01492 = 0.03269 0.00270 0.00531 0.00160 H20A 2 0.619656 0.251930 0.837738 11.00000 0.03417 H20B 2 0.797180 0.245831 0.922688 11.00000 0.03506 H20C 2 0.780277 0.257281 0.783857 11.00000 0.03757 HKLF 4 REM cp32.res in P2(1)/n REM wR2 = 0.0769, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0298 for 3742 Fo > 4sig(Fo) and 0.0303 for all 3828 data REM 320 parameters refined using 0 restraints END WGHT 0.0378 0.8485 REM Highest difference peak 0.382, deepest hole -0.394, 1-sigma level 0.042 Q1 1 0.6324 0.5631 0.7152 11.00000 0.05 0.38 ; _shelx_res_checksum 39485 _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 - B-factor correction ; _oxdiff_exptl_absorpt_empirical_full_max 2.396 _oxdiff_exptl_absorpt_empirical_full_min 0.832 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.52188(3) 0.57121(2) 0.72099(2) 0.01733(10) Uani 1 1 d . . . . . O1 O 0.19187(11) 0.23837(5) 0.73467(8) 0.0271(2) Uani 1 1 d . . . . . H1 H 0.122(2) 0.2067(10) 0.7397(16) 0.044(5) Uiso 1 1 d . . . . . O2 O 0.50188(11) 0.52804(5) 0.81824(8) 0.0257(2) Uani 1 1 d . . . . . O3 O 0.52061(11) 0.64437(4) 0.74870(9) 0.0281(2) Uani 1 1 d . . . . . O4 O 0.41497(11) 0.55352(5) 0.60890(8) 0.0304(2) Uani 1 1 d . . . . . N1 N 0.77877(11) 0.43473(5) 0.74534(8) 0.01474(19) Uani 1 1 d . . . . . C1 C 0.66738(13) 0.39049(5) 0.76485(10) 0.0156(2) Uani 1 1 d . . . . . C2 C 0.93127(13) 0.42588(6) 0.82670(10) 0.0161(2) Uani 1 1 d . . . . . C3 C 1.07651(14) 0.46158(6) 0.83212(10) 0.0197(2) Uani 1 1 d . . . . . H3 H 1.0874(18) 0.4986(8) 0.7794(14) 0.023(4) Uiso 1 1 d . . . . . C4 C 1.21080(14) 0.44007(6) 0.91757(11) 0.0227(2) Uani 1 1 d . . . . . H4 H 1.314(2) 0.4652(8) 0.9238(14) 0.028(4) Uiso 1 1 d . . . . . C5 C 1.19713(15) 0.38578(7) 0.99273(11) 0.0238(3) Uani 1 1 d . . . . . H5 H 1.292(2) 0.3717(8) 1.0502(14) 0.027(4) Uiso 1 1 d . . . . . C6 C 1.04880(15) 0.35156(6) 0.98647(11) 0.0229(2) Uani 1 1 d . . . . . H6 H 1.0392(19) 0.3132(8) 1.0388(14) 0.027(4) Uiso 1 1 d . . . . . C7 C 0.91429(14) 0.37255(6) 0.90181(10) 0.0176(2) Uani 1 1 d . . . . . C8 C 0.73897(13) 0.34706(6) 0.87340(10) 0.0171(2) Uani 1 1 d . . . . . C9 C 0.50568(14) 0.38852(6) 0.69312(10) 0.0182(2) Uani 1 1 d . . . . . H9 H 0.4829(18) 0.4202(8) 0.6305(14) 0.022(4) Uiso 1 1 d . . . . . C10 C 0.38692(14) 0.34625(6) 0.71346(10) 0.0183(2) Uani 1 1 d . . . . . H10 H 0.4111(18) 0.3131(8) 0.7781(13) 0.022(4) Uiso 1 1 d . . . . . C11 C 0.22007(13) 0.34440(6) 0.64498(10) 0.0167(2) Uani 1 1 d . . . . . C12 C 0.12195(14) 0.28754(6) 0.65913(10) 0.0183(2) Uani 1 1 d . . . . . C13 C -0.03949(14) 0.28341(6) 0.59361(11) 0.0211(2) Uani 1 1 d . . . . . H13 H -0.1040(19) 0.2449(8) 0.6042(14) 0.027(4) Uiso 1 1 d . . . . . C14 C -0.10314(14) 0.33521(7) 0.51602(11) 0.0221(2) Uani 1 1 d . . . . . H14 H -0.211(2) 0.3322(9) 0.4711(15) 0.032(4) Uiso 1 1 d . . . . . C15 C -0.00805(15) 0.39242(6) 0.50262(11) 0.0214(2) Uani 1 1 d . . . . . H15 H -0.0559(19) 0.4276(8) 0.4475(14) 0.026(4) Uiso 1 1 d . . . . . C16 C 0.15132(14) 0.39691(6) 0.56694(10) 0.0192(2) Uani 1 1 d . . . . . H16 H 0.2135(19) 0.4386(8) 0.5620(13) 0.023(4) Uiso 1 1 d . . . . . C17 C 0.75848(13) 0.48831(5) 0.65426(10) 0.0156(2) Uani 1 1 d . . . . . H17A H 0.6719(18) 0.4759(7) 0.5893(13) 0.018(3) Uiso 1 1 d . . . . . H17B H 0.8623(17) 0.4897(7) 0.6266(12) 0.016(3) Uiso 1 1 d . . . . . C18 C 0.72711(14) 0.55865(6) 0.70195(10) 0.0175(2) Uani 1 1 d . . . . . H18A H 0.7997(19) 0.5678(8) 0.7789(14) 0.025(4) Uiso 1 1 d . . . . . H18B H 0.7443(19) 0.5939(8) 0.6476(14) 0.025(4) Uiso 1 1 d . . . . . C19 C 0.65412(15) 0.36710(7) 0.97525(11) 0.0233(2) Uani 1 1 d . . . . . H19A H 0.541(2) 0.3509(8) 0.9580(14) 0.026(4) Uiso 1 1 d . . . . . H19B H 0.715(2) 0.3481(9) 1.0503(16) 0.036(4) Uiso 1 1 d . . . . . H19C H 0.652(2) 0.4165(9) 0.9843(15) 0.035(4) Uiso 1 1 d . . . . . C20 C 0.73164(16) 0.26930(6) 0.85129(12) 0.0240(3) Uani 1 1 d . . . . . H20A H 0.620(2) 0.2519(9) 0.8377(15) 0.034(4) Uiso 1 1 d . . . . . H20B H 0.797(2) 0.2458(9) 0.9227(15) 0.035(4) Uiso 1 1 d . . . . . H20C H 0.780(2) 0.2573(9) 0.7839(16) 0.038(4) Uiso 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 0.01471(14) 0.01633(15) 0.01994(16) -0.00285(9) 0.00142(10) 0.00253(9) O1 0.0214(4) 0.0204(4) 0.0353(5) 0.0100(4) -0.0035(4) -0.0063(3) O2 0.0236(4) 0.0277(5) 0.0284(5) 0.0005(4) 0.0112(4) -0.0017(3) O3 0.0245(4) 0.0184(4) 0.0410(5) -0.0062(4) 0.0055(4) 0.0050(3) O4 0.0246(5) 0.0342(5) 0.0268(5) -0.0071(4) -0.0070(4) 0.0076(4) N1 0.0133(4) 0.0142(4) 0.0164(4) -0.0002(3) 0.0025(3) 0.0007(3) C1 0.0164(5) 0.0128(5) 0.0180(5) -0.0012(4) 0.0047(4) 0.0008(4) C2 0.0142(5) 0.0172(5) 0.0164(5) -0.0019(4) 0.0021(4) 0.0022(4) C3 0.0168(5) 0.0200(5) 0.0226(6) -0.0015(4) 0.0050(4) -0.0010(4) C4 0.0148(5) 0.0263(6) 0.0263(6) -0.0072(5) 0.0029(5) -0.0010(4) C5 0.0175(5) 0.0287(6) 0.0225(6) -0.0035(5) -0.0018(5) 0.0051(5) C6 0.0217(6) 0.0245(6) 0.0211(6) 0.0032(5) 0.0015(5) 0.0042(5) C7 0.0160(5) 0.0180(5) 0.0187(5) -0.0006(4) 0.0035(4) 0.0013(4) C8 0.0160(5) 0.0156(5) 0.0194(5) 0.0025(4) 0.0031(4) 0.0007(4) C9 0.0168(5) 0.0162(5) 0.0206(5) 0.0009(4) 0.0016(4) -0.0002(4) C10 0.0176(5) 0.0160(5) 0.0205(5) -0.0004(4) 0.0023(4) 0.0000(4) C11 0.0155(5) 0.0168(5) 0.0180(5) -0.0017(4) 0.0037(4) -0.0010(4) C12 0.0181(5) 0.0168(5) 0.0199(5) -0.0001(4) 0.0036(4) -0.0002(4) C13 0.0171(5) 0.0209(6) 0.0251(6) -0.0022(4) 0.0041(4) -0.0043(4) C14 0.0149(5) 0.0281(6) 0.0220(6) -0.0027(5) 0.0009(4) 0.0004(4) C15 0.0202(5) 0.0237(6) 0.0200(5) 0.0030(4) 0.0038(4) 0.0040(4) C16 0.0192(5) 0.0183(5) 0.0208(5) 0.0010(4) 0.0060(4) -0.0006(4) C17 0.0163(5) 0.0149(5) 0.0160(5) 0.0016(4) 0.0046(4) 0.0002(4) C18 0.0171(5) 0.0146(5) 0.0218(5) 0.0006(4) 0.0061(4) -0.0005(4) C19 0.0223(6) 0.0275(6) 0.0214(6) 0.0012(5) 0.0072(5) 0.0007(5) C20 0.0241(6) 0.0149(5) 0.0327(7) 0.0027(5) 0.0053(5) 0.0016(4) 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' 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' S S 0.3331 0.5567 '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 -8 6 0.0389 0 8 -6 0.0703 0 -9 -5 0.0342 0 9 5 0.0884 0 0 -1 0.0406 0 0 1 0.0572 0 1 0 0.0940 1 -2 0 0.1420 2 1 -1 0.1744 1 0 2 0.1143 -2 -1 1 0.3836 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 O2 S1 O3 113.03(6) . . ? O2 S1 O4 114.03(6) . . ? O2 S1 C18 106.72(5) . . ? O3 S1 C18 102.25(5) . . ? O4 S1 O3 113.33(6) . . ? O4 S1 C18 106.28(6) . . ? C12 O1 H1 110.5(13) . . ? C1 N1 C2 111.69(9) . . ? C1 N1 C17 127.52(9) . . ? C2 N1 C17 120.79(9) . . ? N1 C1 C8 109.64(9) . . ? N1 C1 C9 122.02(10) . . ? C9 C1 C8 128.31(10) . . ? C3 C2 N1 128.19(10) . . ? C7 C2 N1 108.12(10) . . ? C7 C2 C3 123.67(11) . . ? C2 C3 H3 123.2(9) . . ? C2 C3 C4 116.36(11) . . ? C4 C3 H3 120.4(9) . . ? C3 C4 H4 117.6(9) . . ? C5 C4 C3 120.90(11) . . ? C5 C4 H4 121.5(9) . . ? C4 C5 H5 119.3(10) . . ? C4 C5 C6 121.45(11) . . ? C6 C5 H5 119.2(10) . . ? C5 C6 H6 121.6(9) . . ? C7 C6 C5 118.15(11) . . ? C7 C6 H6 120.3(9) . . ? C2 C7 C6 119.45(11) . . ? C2 C7 C8 109.50(10) . . ? C6 C7 C8 131.05(11) . . ? C1 C8 C19 108.87(9) . . ? C1 C8 C20 114.57(10) . . ? C7 C8 C1 100.81(9) . . ? C7 C8 C19 109.14(9) . . ? C7 C8 C20 111.29(9) . . ? C20 C8 C19 111.56(10) . . ? C1 C9 H9 116.3(9) . . ? C10 C9 C1 123.65(11) . . ? C10 C9 H9 120.0(9) . . ? C9 C10 H10 119.9(9) . . ? C9 C10 C11 125.18(11) . . ? C11 C10 H10 114.9(9) . . ? C12 C11 C10 118.06(10) . . ? C16 C11 C10 123.17(10) . . ? C16 C11 C12 118.76(10) . . ? O1 C12 C11 117.06(10) . . ? O1 C12 C13 123.06(10) . . ? C13 C12 C11 119.86(10) . . ? C12 C13 H13 118.9(10) . . ? C14 C13 C12 120.19(11) . . ? C14 C13 H13 120.9(10) . . ? C13 C14 H14 120.3(10) . . ? C13 C14 C15 120.53(11) . . ? C15 C14 H14 119.2(10) . . ? C14 C15 H15 118.5(9) . . ? C16 C15 C14 119.66(11) . . ? C16 C15 H15 121.9(9) . . ? C11 C16 H16 119.8(9) . . ? C15 C16 C11 120.98(11) . . ? C15 C16 H16 119.0(9) . . ? N1 C17 H17A 109.6(9) . . ? N1 C17 H17B 106.1(8) . . ? N1 C17 C18 112.61(9) . . ? H17A C17 H17B 108.7(11) . . ? C18 C17 H17A 110.7(8) . . ? C18 C17 H17B 108.9(8) . . ? S1 C18 H18A 106.7(9) . . ? S1 C18 H18B 105.1(9) . . ? C17 C18 S1 114.24(8) . . ? C17 C18 H18A 111.8(9) . . ? C17 C18 H18B 110.3(9) . . ? H18A C18 H18B 108.3(13) . . ? C8 C19 H19A 109.9(9) . . ? C8 C19 H19B 110.2(10) . . ? C8 C19 H19C 110.9(10) . . ? H19A C19 H19B 110.7(14) . . ? H19A C19 H19C 107.8(14) . . ? H19B C19 H19C 107.4(14) . . ? C8 C20 H20A 111.9(10) . . ? C8 C20 H20B 108.6(10) . . ? C8 C20 H20C 111.1(10) . . ? H20A C20 H20B 108.1(14) . . ? H20A C20 H20C 109.4(14) . . ? H20B C20 H20C 107.6(14) . . ? 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 O2 1.4431(9) . ? S1 O3 1.4640(9) . ? S1 O4 1.4513(9) . ? S1 C18 1.7880(12) . ? O1 H1 0.86(2) . ? O1 C12 1.3450(14) . ? N1 C1 1.3220(14) . ? N1 C2 1.4235(14) . ? N1 C17 1.4687(13) . ? C1 C8 1.5280(15) . ? C1 C9 1.4265(15) . ? C2 C3 1.3871(16) . ? C2 C7 1.3823(16) . ? C3 H3 0.962(16) . ? C3 C4 1.3924(17) . ? C4 H4 0.978(16) . ? C4 C5 1.3906(19) . ? C5 H5 0.957(16) . ? C5 C6 1.3941(18) . ? C6 H6 0.977(16) . ? C6 C7 1.3857(16) . ? C7 C8 1.5131(15) . ? C8 C19 1.5476(16) . ? C8 C20 1.5379(15) . ? C9 H9 0.940(15) . ? C9 C10 1.3474(16) . ? C10 H10 0.978(15) . ? C10 C11 1.4486(15) . ? C11 C12 1.4086(15) . ? C11 C16 1.4054(16) . ? C12 C13 1.4005(16) . ? C13 H13 0.947(16) . ? C13 C14 1.3812(17) . ? C14 H14 0.943(17) . ? C14 C15 1.3970(17) . ? C15 H15 0.964(16) . ? C15 C16 1.3817(17) . ? C16 H16 0.973(16) . ? C17 H17A 0.957(15) . ? C17 H17B 0.985(14) . ? C17 C18 1.5226(15) . ? C18 H18A 0.981(16) . ? C18 H18B 0.962(16) . ? C19 H19A 0.972(16) . ? C19 H19B 0.980(18) . ? C19 H19C 0.970(18) . ? C20 H20A 0.974(18) . ? C20 H20B 1.000(17) . ? C20 H20C 0.981(18) . ? 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 _geom_hbond_publ_flag O1 H1 O3 0.86(2) 1.73(2) 2.5856(12) 179(2) 2_546 yes 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 C12 C13 C14 -178.94(11) . . . . ? O2 S1 C18 C17 69.57(9) . . . . ? O3 S1 C18 C17 -171.53(8) . . . . ? O4 S1 C18 C17 -52.48(10) . . . . ? N1 C1 C8 C7 -4.55(11) . . . . ? N1 C1 C8 C19 110.17(10) . . . . ? N1 C1 C8 C20 -124.14(10) . . . . ? N1 C1 C9 C10 -176.98(11) . . . . ? N1 C2 C3 C4 -176.85(11) . . . . ? N1 C2 C7 C6 177.08(10) . . . . ? N1 C2 C7 C8 -3.24(12) . . . . ? N1 C17 C18 S1 -77.60(11) . . . . ? C1 N1 C2 C3 178.55(11) . . . . ? C1 N1 C2 C7 0.15(13) . . . . ? C1 N1 C17 C18 98.78(13) . . . . ? C1 C9 C10 C11 177.85(11) . . . . ? C2 N1 C1 C8 2.97(12) . . . . ? C2 N1 C1 C9 -178.79(10) . . . . ? C2 N1 C17 C18 -80.62(12) . . . . ? C2 C3 C4 C5 -0.19(17) . . . . ? C2 C7 C8 C1 4.62(12) . . . . ? C2 C7 C8 C19 -109.89(11) . . . . ? C2 C7 C8 C20 126.55(11) . . . . ? C3 C2 C7 C6 -1.41(18) . . . . ? C3 C2 C7 C8 178.27(10) . . . . ? C3 C4 C5 C6 -0.84(19) . . . . ? C4 C5 C6 C7 0.77(18) . . . . ? C5 C6 C7 C2 0.32(17) . . . . ? C5 C6 C7 C8 -179.29(11) . . . . ? C6 C7 C8 C1 -175.74(12) . . . . ? C6 C7 C8 C19 69.75(16) . . . . ? C6 C7 C8 C20 -53.82(17) . . . . ? C7 C2 C3 C4 1.33(17) . . . . ? C8 C1 C9 C10 0.90(19) . . . . ? C9 C1 C8 C7 177.36(11) . . . . ? C9 C1 C8 C19 -67.93(14) . . . . ? C9 C1 C8 C20 57.76(15) . . . . ? C9 C10 C11 C12 165.43(11) . . . . ? C9 C10 C11 C16 -15.57(18) . . . . ? C10 C11 C12 O1 -0.87(16) . . . . ? C10 C11 C12 C13 -179.31(10) . . . . ? C10 C11 C16 C15 179.33(11) . . . . ? C11 C12 C13 C14 -0.59(17) . . . . ? C12 C11 C16 C15 -1.69(17) . . . . ? C12 C13 C14 C15 -0.48(18) . . . . ? C13 C14 C15 C16 0.46(18) . . . . ? C14 C15 C16 C11 0.64(18) . . . . ? C16 C11 C12 O1 -179.91(10) . . . . ? C16 C11 C12 C13 1.65(16) . . . . ? C17 N1 C1 C8 -176.48(9) . . . . ? C17 N1 C1 C9 1.76(17) . . . . ? C17 N1 C2 C3 -1.95(17) . . . . ? C17 N1 C2 C7 179.64(9) . . . . ? 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 0.0400 -8.1812 5.5922 -0.9704 0.0251 -0.2404 -0.0464 8.1819 -5.5899 0.9706 -0.0251 0.2392 -0.2493 -8.6848 -5.2585 0.0790 -0.9959 0.0435 0.2043 8.6689 5.2839 -0.0790 0.9955 -0.0521 0.0000 0.0000 -1.0000 0.0971 -0.0903 0.0311 -0.0000 -0.0000 1.0000 -0.0971 0.0903 -0.0311 -0.0000 1.0000 0.0000 0.0518 0.0589 0.0090 1.0000 -2.0000 -0.0000 -0.1776 -0.0784 0.1516 2.0000 1.0000 -1.0000 0.0012 0.0473 0.3790 1.0000 -0.0000 2.0000 -0.2682 0.2200 0.1073 -2.0000 -1.0000 1.0000 -0.0012 -0.0473 -0.3790