#------------------------------------------------------------------------------ #$Date: 2019-12-25 03:45:57 +0200 (Wed, 25 Dec 2019) $ #$Revision: 245567 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125692.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_7125692 loop_ _publ_author_name 'Escolano, Marcos' 'Guerola, Marta' 'Torres Fern\'andez, Javier' 'Daniel, Gavi\~na' 'Alzuet, Gloria' 'Sanchez-Rosello, Maria' 'del Pozo Losada, Carlos' _publ_section_title ; Organocatalytic Enantioselective Synthesis of 2,5,5-Trisubstituted Piperidines Bearing a Quaternary Stereocenter. Vinyl Sulfonamide as New Amine Protecting Group ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC09113K _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C14 H24 N2 O5 S2' _chemical_formula_sum 'C14 H24 N2 O5 S2' _chemical_formula_weight 364.48 _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-01-09T13:55:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2019-01-15 deposited with the CCDC. 2019-12-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.4852(9) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.25874(8) _cell_length_b 6.61591(6) _cell_length_c 18.72215(18) _cell_measurement_reflns_used 6625 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 74.28 _cell_measurement_theta_min 4.687 _cell_volume 898.795(15) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2012 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _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 -102.00 -61.00 1.00 1.00 -- -42.13-152.00 3.00 41 2 \w -121.00 -25.00 1.00 1.00 -- -42.13 -19.00 60.00 96 3 \w 12.00 97.00 1.00 1.00 -- 42.13-125.00-120.00 85 4 \w 80.00 106.00 1.00 1.00 -- 42.13 152.00 46.00 26 5 \w -25.00 60.00 1.00 1.00 -- 42.13 -57.00 0.00 85 6 \w 73.00 107.00 1.00 1.00 -- 107.93 -94.00 60.00 34 7 \w 27.00 67.00 1.00 1.00 -- 107.93 -94.00 60.00 40 8 \w 32.00 140.00 1.00 1.00 -- 107.93 -77.00-120.00 108 9 \w 35.00 61.00 1.00 1.00 -- 107.93 -30.00-120.00 26 10 \w 84.00 133.00 1.00 1.00 -- 107.93 45.00 60.00 49 11 \w 36.00 62.00 1.00 1.00 -- 107.93 -30.00 120.00 26 12 \w 98.00 147.00 1.00 1.00 -- 107.93 45.00 90.00 49 13 \w 40.00 70.00 1.00 1.00 -- 107.93-125.00 60.00 30 14 \w 79.00 112.00 1.00 1.00 -- 107.93-125.00 60.00 33 15 \w 36.00 67.00 1.00 1.00 -- 107.93 -30.00-150.00 31 16 \w 43.00 116.00 1.00 1.00 -- 107.93-125.00-120.00 73 17 \w 79.00 155.00 1.00 1.00 -- 107.93 61.00-180.00 76 18 \w 123.00 153.00 1.00 1.00 -- 107.93 45.00 -90.00 30 19 \w 126.00 157.00 1.00 1.00 -- 107.93 97.00 -8.00 31 20 \w 83.00 138.00 1.00 1.00 -- 107.93 125.00 90.00 55 21 \w 76.00 158.00 1.00 1.00 -- 107.93 125.00-150.00 82 22 \w -80.00 -22.00 1.00 1.00 -- -42.13 19.00 90.00 58 23 \w 39.00 68.00 1.00 1.00 -- 107.93 -30.00 60.00 29 24 \w 37.00 64.00 1.00 1.00 -- 107.93 -30.00-180.00 27 25 \w 69.00 96.00 1.00 1.00 -- 107.93-125.00-180.00 27 26 \w 99.00 157.00 1.00 1.00 -- 107.93 77.00 -30.00 58 27 \w 41.00 67.00 1.00 1.00 -- 107.93 -45.00 90.00 26 ; _diffrn_measurement_device 'four-circle\k-geometry diffractometer' _diffrn_measurement_device_type 'Agilent SuperNova' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0067621 _diffrn_orient_matrix_UB_12 -0.1002634 _diffrn_orient_matrix_UB_13 -0.074161 _diffrn_orient_matrix_UB_21 -0.0772762 _diffrn_orient_matrix_UB_22 0.194557 _diffrn_orient_matrix_UB_23 -0.0346711 _diffrn_orient_matrix_UB_31 0.1976133 _diffrn_orient_matrix_UB_32 0.0794087 _diffrn_orient_matrix_UB_33 -0.0087125 _diffrn_radiation_monochromator 'Multilayer optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_unetI/netI 0.0339 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 7162 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.949 _diffrn_reflns_theta_min 4.725 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.8 _diffrn_source_power 0.04 _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 2.918 _exptl_absorpt_correction_T_max 0.819 _exptl_absorpt_correction_T_min 0.283 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.35 _exptl_crystal_description prism _exptl_crystal_F_000 390 _exptl_crystal_size_max 0.589 _exptl_crystal_size_mid 0.335 _exptl_crystal_size_min 0.072 _refine_diff_density_max 0.268 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details ; Flack x determined using 1456 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). The Friedel pair coverage of the experiment is almost complete (99%). Analysis of the absolute structure using likelihood methods (Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2009). The resulting value was y=-0.001(6) ; _refine_ls_abs_structure_Flack 0.005(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3310 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0248 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.0657 _reflns_Friedel_coverage 0.825 _reflns_Friedel_fraction_full 0.997 _reflns_Friedel_fraction_max 0.991 _reflns_number_gt 3275 _reflns_number_total 3310 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL a20180275_mp2991_a.res in P2(1) a20180275_mp2991.res created by SHELXL-2018/3 at 12:09:15 on 09-Jan-2019 REM Old TITL a20180275_MP2991 in P21 #4 REM SHELXT solution in P2(1): R1 0.085, Rweak 0.037, Alpha 0.003 REM 0.764 for 4 systematic absences, Orientation as input REM Flack x = 0.153 ( 0.006 ) from 1536 Parsons' quotients REM Formula found by SHELXT: C13 N2 O6 Cl2 CELL 1.54184 7.258737 6.615912 18.722154 90 91.4852 90 ZERR 2 0.000079 0.000065 0.00018 0 0.0009 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 28 50 4 10 4 DFIX 0.98 0.01 C10 H10b C10 H10a C7 H7a C7 H7b DFIX 0.88 0.01 N2 H2 DANG 1.67 0.02 H7a H7b DANG 1.67 0.02 H10a H10b L.S. 10 PLAN 5 BOND list 4 bond $H conf fmap 2 acta OMIT -2 138 REM REM REM WGHT 0.040900 0.113100 FVAR 13.43198 S1 5 0.161514 0.521091 0.306142 11.00000 0.01624 0.01792 = 0.01993 0.00187 -0.00270 -0.00073 S2 5 0.718084 0.330971 0.072900 11.00000 0.02773 0.02497 = 0.01849 0.00028 -0.00272 -0.00551 O1 4 0.085881 0.643841 0.361709 11.00000 0.02140 0.02404 = 0.03203 -0.00377 0.00334 0.00053 O2 4 0.078683 0.527102 0.235842 11.00000 0.02235 0.03203 = 0.02720 0.00521 -0.00977 -0.00386 O3 4 0.767902 0.229964 0.138058 11.00000 0.03792 0.02926 = 0.02696 0.00785 -0.00522 -0.00481 O4 4 0.602014 0.230302 0.020938 11.00000 0.04287 0.04399 = 0.02917 -0.01018 -0.01019 -0.00885 O5 4 0.634907 0.708054 0.499957 11.00000 0.05012 0.05147 = 0.02603 -0.01309 -0.01163 0.01474 N1 3 0.375297 0.580870 0.300274 11.00000 0.01964 0.02965 = 0.01715 -0.00306 -0.00082 -0.00593 N2 3 0.613834 0.537482 0.092033 11.00000 0.02588 0.03421 = 0.01573 -0.00031 -0.00503 0.00244 C1 1 0.478502 0.533669 0.236155 11.00000 0.02124 0.02262 = 0.01640 -0.00183 -0.00151 -0.00277 AFIX 23 H1A 2 0.397680 0.469195 0.200934 11.00000 -1.20000 H1B 2 0.577902 0.440753 0.248200 11.00000 -1.20000 AFIX 0 C2 1 0.557763 0.728878 0.204997 11.00000 0.01954 0.02254 = 0.01738 0.00096 -0.00235 -0.00095 C3 1 0.669015 0.840056 0.264018 11.00000 0.02041 0.02095 = 0.02392 -0.00011 -0.00223 -0.00244 AFIX 23 H3A 2 0.781434 0.765103 0.274330 11.00000 -1.20000 H3B 2 0.703798 0.972096 0.246326 11.00000 -1.20000 AFIX 0 C4 1 0.564978 0.867518 0.333614 11.00000 0.02362 0.02336 = 0.02383 -0.00462 -0.00555 -0.00004 AFIX 23 H4A 2 0.648917 0.921469 0.369989 11.00000 -1.20000 H4B 2 0.466962 0.965310 0.325779 11.00000 -1.20000 AFIX 0 C5 1 0.482294 0.670836 0.360703 11.00000 0.01797 0.02821 = 0.01707 -0.00491 -0.00225 -0.00179 AFIX 13 H5 2 0.396419 0.704170 0.398484 11.00000 -1.20000 AFIX 0 C6 1 0.152344 0.271484 0.336093 11.00000 0.02228 0.02124 = 0.02568 0.00445 -0.00269 0.00031 AFIX 43 H6 2 0.207634 0.237760 0.379849 11.00000 -1.20000 AFIX 0 C7 1 0.068987 0.130729 0.298061 11.00000 0.03411 0.02172 = 0.04300 -0.00124 -0.00348 -0.00194 H7A 2 0.065576 -0.005999 0.316443 11.00000 0.03712 H7B 2 0.013301 0.162521 0.251190 11.00000 0.04357 H2 2 0.548302 0.580669 0.054944 11.00000 -1.20000 C8 1 0.694101 0.673725 0.146514 11.00000 0.02093 0.02758 = 0.01978 0.00193 -0.00102 -0.00253 AFIX 23 H8A 2 0.734774 0.796678 0.123512 11.00000 -1.20000 H8B 2 0.801444 0.609507 0.168532 11.00000 -1.20000 AFIX 0 C9 1 0.922154 0.396892 0.030387 11.00000 0.03965 0.02939 = 0.02748 -0.00376 0.00909 -0.00329 AFIX 43 H9 2 0.915171 0.442659 -0.016572 11.00000 -1.20000 AFIX 0 C10 1 1.083125 0.383804 0.062470 11.00000 0.03445 0.04824 = 0.04944 -0.01250 0.00936 -0.00802 H10A 2 1.093502 0.339839 0.112014 11.00000 0.06090 H10B 2 1.196969 0.418605 0.038545 11.00000 0.04225 C11 1 0.402094 0.860730 0.173238 11.00000 0.02479 0.02921 = 0.02584 0.00369 -0.00300 0.00266 AFIX 137 H11A 2 0.340890 0.789499 0.134769 11.00000 -1.50000 H11B 2 0.452798 0.984430 0.155519 11.00000 -1.50000 H11C 2 0.315242 0.890717 0.209565 11.00000 -1.50000 AFIX 0 C12 1 0.623526 0.519591 0.391081 11.00000 0.02306 0.02486 = 0.01887 0.00000 -0.00171 -0.00183 AFIX 23 H12A 2 0.567919 0.386274 0.391149 11.00000 -1.20000 H12B 2 0.727604 0.514902 0.359656 11.00000 -1.20000 AFIX 0 C13 1 0.693655 0.567642 0.465930 11.00000 0.02631 0.03231 = 0.01989 0.00189 -0.00215 -0.00160 C14 1 0.840050 0.429366 0.494906 11.00000 0.03557 0.04121 = 0.02286 0.00554 -0.00468 0.00387 AFIX 137 H14A 2 0.952294 0.452049 0.470102 11.00000 -1.50000 H14B 2 0.801661 0.291621 0.488311 11.00000 -1.50000 H14C 2 0.860295 0.455547 0.544930 11.00000 -1.50000 AFIX 0 HKLF 4 REM a20180275_mp2991_a.res in P2(1) REM wR2 = 0.0657, GooF = S = 1.059, Restrained GooF = 1.058 for all data REM R1 = 0.0248 for 3275 Fo > 4sig(Fo) and 0.0251 for all 3310 data REM 229 parameters refined using 8 restraints END WGHT 0.0409 0.1130 REM Highest difference peak 0.268, deepest hole -0.316, 1-sigma level 0.054 Q1 1 0.2839 0.5388 0.3035 11.00000 0.05 0.27 Q2 1 0.4580 1.1758 0.1241 11.00000 0.05 0.15 Q3 1 0.3363 0.5006 0.2025 11.00000 0.05 0.15 Q4 1 0.4085 0.6311 0.3222 11.00000 0.05 0.15 Q5 1 0.7614 0.1783 0.4719 11.00000 0.05 0.14 REM The information below was added by Olex2. REM REM R1 = 0.0248 for 3275 Fo > 4sig(Fo) and 0.0251 for all 7471 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.27, deepest hole -0.32 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0251 REM R1_gt = 0.0248 REM wR_ref = 0.0657 REM GOOF = 1.059 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 7471 REM Reflections_gt = 3275 REM Parameters = n/a REM Hole = -0.32 REM Peak = 0.27 REM Flack = 0.005(7) ; _cod_data_source_file c9cc09113k2.cif _cod_data_source_block a20180275_mp2991 _cod_original_cell_volume 898.795(16) _cod_database_code 7125692 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 S1 S 0.16151(7) 0.52109(8) 0.30614(3) 0.01808(13) Uani 1 1 d . S2 S 0.71808(8) 0.33097(8) 0.07290(3) 0.02379(15) Uani 1 1 d . O1 O 0.0859(2) 0.6438(3) 0.36171(9) 0.0258(4) Uani 1 1 d . O2 O 0.0787(2) 0.5271(3) 0.23584(8) 0.0274(4) Uani 1 1 d . O3 O 0.7679(2) 0.2300(3) 0.13806(9) 0.0315(4) Uani 1 1 d . O4 O 0.6020(3) 0.2303(3) 0.02094(10) 0.0389(5) Uani 1 1 d . O5 O 0.6349(3) 0.7081(4) 0.49996(10) 0.0428(5) Uani 1 1 d . N1 N 0.3753(3) 0.5809(3) 0.30027(10) 0.0222(4) Uani 1 1 d . N2 N 0.6138(3) 0.5375(4) 0.09203(10) 0.0254(4) Uani 1 1 d D C1 C 0.4785(3) 0.5337(4) 0.23616(10) 0.0201(4) Uani 1 1 d . H1A H 0.39768 0.469194 0.200934 0.024 Uiso 1 1 calc R H1B H 0.577902 0.440752 0.2482 0.024 Uiso 1 1 calc R C2 C 0.5578(3) 0.7289(3) 0.20500(11) 0.0199(4) Uani 1 1 d . C3 C 0.6690(3) 0.8401(4) 0.26402(12) 0.0218(5) Uani 1 1 d . H3A H 0.781434 0.765102 0.27433 0.026 Uiso 1 1 calc R H3B H 0.703798 0.972095 0.246327 0.026 Uiso 1 1 calc R C4 C 0.5650(3) 0.8675(4) 0.33361(13) 0.0237(5) Uani 1 1 d . H4A H 0.648917 0.921468 0.369989 0.028 Uiso 1 1 calc R H4B H 0.466962 0.965309 0.325779 0.028 Uiso 1 1 calc R C5 C 0.4823(3) 0.6708(4) 0.36070(11) 0.0211(4) Uani 1 1 d . H5 H 0.396419 0.704169 0.398485 0.025 Uiso 1 1 calc R C6 C 0.1523(3) 0.2715(3) 0.33609(13) 0.0231(5) Uani 1 1 d . H6 H 0.207634 0.23776 0.379849 0.028 Uiso 1 1 calc R C7 C 0.0690(4) 0.1307(4) 0.29806(16) 0.0330(6) Uani 1 1 d D H7A H 0.066(4) -0.006(3) 0.3164(14) 0.037(8) Uiso 1 1 d D H7B H 0.013(4) 0.163(5) 0.2512(10) 0.044(9) Uiso 1 1 d D H2 H 0.548(4) 0.581(6) 0.0549(13) 0.052 Uiso 1 1 d DR C8 C 0.6941(3) 0.6737(4) 0.14651(12) 0.0228(5) Uani 1 1 d . H8A H 0.734774 0.796678 0.123512 0.027 Uiso 1 1 calc R H8B H 0.801444 0.609506 0.168532 0.027 Uiso 1 1 calc R C9 C 0.9222(4) 0.3969(4) 0.03039(14) 0.0320(6) Uani 1 1 d . H9 H 0.915171 0.442658 -0.016572 0.038 Uiso 1 1 calc R C10 C 1.0831(4) 0.3838(5) 0.06247(18) 0.0439(7) Uani 1 1 d D H10A H 1.094(5) 0.340(6) 0.1120(10) 0.061(11) Uiso 1 1 d D H10B H 1.197(3) 0.419(5) 0.0385(15) 0.042(9) Uiso 1 1 d D C11 C 0.4021(3) 0.8607(4) 0.17324(13) 0.0267(5) Uani 1 1 d . H11A H 0.340891 0.789498 0.134768 0.04 Uiso 1 1 calc GR H11B H 0.452798 0.984429 0.155519 0.04 Uiso 1 1 calc GR H11C H 0.315242 0.890716 0.209565 0.04 Uiso 1 1 calc GR C12 C 0.6235(3) 0.5196(4) 0.39108(11) 0.0223(4) Uani 1 1 d . H12A H 0.567919 0.386273 0.391149 0.027 Uiso 1 1 calc R H12B H 0.727604 0.514902 0.359656 0.027 Uiso 1 1 calc R C13 C 0.6937(3) 0.5676(4) 0.46593(12) 0.0262(5) Uani 1 1 d . C14 C 0.8400(4) 0.4294(4) 0.49491(13) 0.0333(6) Uani 1 1 d . H14A H 0.952294 0.452048 0.470102 0.05 Uiso 1 1 calc GR H14B H 0.801661 0.29162 0.488311 0.05 Uiso 1 1 calc GR H14C H 0.860295 0.455547 0.54493 0.05 Uiso 1 1 calc GR 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 0.0162(2) 0.0179(2) 0.0199(2) 0.0019(2) -0.00270(17) -0.00073(19) S2 0.0277(3) 0.0250(3) 0.0185(3) 0.0003(2) -0.0027(2) -0.0055(2) O1 0.0214(8) 0.0240(9) 0.0320(9) -0.0038(7) 0.0033(6) 0.0005(7) O2 0.0224(7) 0.0320(9) 0.0272(8) 0.0052(8) -0.0098(6) -0.0039(8) O3 0.0379(10) 0.0293(9) 0.0270(9) 0.0078(7) -0.0052(7) -0.0048(8) O4 0.0429(11) 0.0440(11) 0.0292(9) -0.0102(9) -0.0102(8) -0.0088(9) O5 0.0501(12) 0.0515(12) 0.0260(9) -0.0131(9) -0.0116(8) 0.0147(10) N1 0.0196(9) 0.0296(11) 0.0171(9) -0.0031(7) -0.0008(7) -0.0059(8) N2 0.0259(9) 0.0342(11) 0.0157(8) -0.0003(9) -0.0050(7) 0.0024(9) C1 0.0212(10) 0.0226(11) 0.0164(10) -0.0018(9) -0.0015(8) -0.0028(9) C2 0.0195(10) 0.0225(11) 0.0174(9) 0.0010(9) -0.0023(8) -0.0009(9) C3 0.0204(10) 0.0210(11) 0.0239(11) -0.0001(9) -0.0022(8) -0.0024(9) C4 0.0236(11) 0.0234(12) 0.0238(11) -0.0046(9) -0.0055(9) 0.0000(9) C5 0.0180(10) 0.0282(11) 0.0171(9) -0.0049(9) -0.0022(8) -0.0018(9) C6 0.0223(11) 0.0212(12) 0.0257(11) 0.0045(9) -0.0027(9) 0.0003(8) C7 0.0341(14) 0.0217(13) 0.0430(15) -0.0012(11) -0.0035(11) -0.0019(11) C8 0.0209(11) 0.0276(12) 0.0198(10) 0.0019(9) -0.0010(8) -0.0025(9) C9 0.0396(14) 0.0294(13) 0.0275(12) -0.0038(10) 0.0091(11) -0.0033(11) C10 0.0345(14) 0.0482(18) 0.0494(17) -0.0125(14) 0.0094(13) -0.0080(13) C11 0.0248(11) 0.0292(13) 0.0258(12) 0.0037(10) -0.0030(9) 0.0027(9) C12 0.0231(10) 0.0249(11) 0.0189(10) 0.0000(10) -0.0017(8) -0.0018(10) C13 0.0263(11) 0.0323(14) 0.0199(11) 0.0019(9) -0.0022(9) -0.0016(10) C14 0.0356(14) 0.0412(15) 0.0229(12) 0.0055(11) -0.0047(10) 0.0039(11) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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 5 0 3 0.1378 1 3 -7 0.2055 -4 1 -3 0.1393 0 -3 7 0.1812 4 1 1 0.198 0 0 1 0.0377 -4 -1 0 0.196 0 0 -1 0.0346 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 S1 N1 107.30(10) O1 S1 C6 106.44(11) O2 S1 O1 119.28(10) O2 S1 N1 108.24(10) O2 S1 C6 107.61(12) N1 S1 C6 107.43(11) O3 S2 O4 119.54(12) O3 S2 N2 108.51(10) O3 S2 C9 107.79(12) O4 S2 N2 105.92(11) O4 S2 C9 107.20(12) N2 S2 C9 107.32(12) C1 N1 S1 121.23(15) C1 N1 C5 116.27(17) C5 N1 S1 122.33(15) S2 N2 H2 110(2) C8 N2 S2 119.70(15) C8 N2 H2 123(3) N1 C1 H1A 109.7 N1 C1 H1B 109.7 N1 C1 C2 109.67(19) H1A C1 H1B 108.2 C2 C1 H1A 109.7 C2 C1 H1B 109.7 C1 C2 C3 108.91(17) C1 C2 C8 108.98(19) C8 C2 C3 106.80(17) C11 C2 C1 110.24(18) C11 C2 C3 111.95(19) C11 C2 C8 109.86(18) C2 C3 H3A 108.8 C2 C3 H3B 108.8 H3A C3 H3B 107.7 C4 C3 C2 113.95(18) C4 C3 H3A 108.8 C4 C3 H3B 108.8 C3 C4 H4A 109 C3 C4 H4B 109 H4A C4 H4B 107.8 C5 C4 C3 112.84(19) C5 C4 H4A 109 C5 C4 H4B 109 N1 C5 C4 106.98(18) N1 C5 H5 108.1 N1 C5 C12 110.73(19) C4 C5 H5 108.1 C4 C5 C12 114.55(18) C12 C5 H5 108.1 S1 C6 H6 119.4 C7 C6 S1 121.2(2) C7 C6 H6 119.4 C6 C7 H7A 119.1(17) C6 C7 H7B 120.5(19) H7A C7 H7B 120(2) N2 C8 C2 112.86(18) N2 C8 H8A 109 N2 C8 H8B 109 C2 C8 H8A 109 C2 C8 H8B 109 H8A C8 H8B 107.8 S2 C9 H9 118.9 C10 C9 S2 122.1(2) C10 C9 H9 118.9 C9 C10 H10A 120(2) C9 C10 H10B 122.1(18) H10A C10 H10B 117(2) C2 C11 H11A 109.5 C2 C11 H11B 109.5 C2 C11 H11C 109.5 H11A C11 H11B 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C5 C12 H12A 108.7 C5 C12 H12B 108.7 H12A C12 H12B 107.6 C13 C12 C5 114.4(2) C13 C12 H12A 108.7 C13 C12 H12B 108.7 O5 C13 C12 122.3(2) O5 C13 C14 122.4(2) C14 C13 C12 115.3(2) C13 C14 H14A 109.5 C13 C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.4397(17) S1 O2 1.4333(16) S1 N1 1.6079(19) S1 C6 1.746(2) S2 O3 1.4292(17) S2 O4 1.4343(18) S2 N2 1.607(2) S2 C9 1.755(3) O5 C13 1.210(3) N1 C1 1.465(3) N1 C5 1.481(3) N2 H2 0.879(13) N2 C8 1.470(3) C1 H1A 0.97 C1 H1B 0.97 C1 C2 1.535(3) C2 C3 1.539(3) C2 C8 1.539(3) C2 C11 1.535(3) C3 H3A 0.97 C3 H3B 0.97 C3 C4 1.534(3) C4 H4A 0.97 C4 H4B 0.97 C4 C5 1.525(3) C5 H5 0.98 C5 C12 1.531(3) C6 H6 0.93 C6 C7 1.311(4) C7 H7A 0.968(13) C7 H7B 0.979(13) C8 H8A 0.97 C8 H8B 0.97 C9 H9 0.93 C9 C10 1.303(4) C10 H10A 0.973(13) C10 H10B 0.978(13) C11 H11A 0.96 C11 H11B 0.96 C11 H11C 0.96 C12 H12A 0.97 C12 H12B 0.97 C12 C13 1.512(3) C13 C14 1.493(3) C14 H14A 0.96 C14 H14B 0.96 C14 H14C 0.96 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 S1 N1 C1 C2 122.30(17) S1 N1 C5 C4 -125.14(17) S1 N1 C5 C12 109.40(19) S2 N2 C8 C2 -127.13(18) O1 S1 N1 C1 -160.75(18) O1 S1 N1 C5 24.2(2) O1 S1 C6 C7 124.7(2) O2 S1 N1 C1 -30.8(2) O2 S1 N1 C5 154.18(18) O2 S1 C6 C7 -4.2(2) O3 S2 N2 C8 48.1(2) O3 S2 C9 C10 -11.1(3) O4 S2 N2 C8 177.63(17) O4 S2 C9 C10 -141.0(3) N1 S1 C6 C7 -120.6(2) N1 C1 C2 C3 53.5(2) N1 C1 C2 C8 169.70(17) N1 C1 C2 C11 -69.7(2) N1 C5 C12 C13 -160.67(18) N2 S2 C9 C10 105.6(3) C1 N1 C5 C4 59.6(2) C1 N1 C5 C12 -65.8(2) C1 C2 C3 C4 -50.3(2) C1 C2 C8 N2 53.0(2) C2 C3 C4 C5 51.0(3) C3 C2 C8 N2 170.53(19) C3 C4 C5 N1 -51.4(2) C3 C4 C5 C12 71.7(2) C4 C5 C12 C13 78.3(2) C5 N1 C1 C2 -62.4(2) C5 C12 C13 O5 3.8(3) C5 C12 C13 C14 -176.4(2) C6 S1 N1 C1 85.1(2) C6 S1 N1 C5 -89.88(19) C8 C2 C3 C4 -167.84(19) C9 S2 N2 C8 -68.1(2) C11 C2 C3 C4 71.9(2) C11 C2 C8 N2 -67.8(2)