#------------------------------------------------------------------------------ #$Date: 2019-02-22 03:59:13 +0200 (Fri, 22 Feb 2019) $ #$Revision: 213783 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/82/7058203.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_7058203 loop_ _publ_author_name 'Zou, Dongyu' 'Liu, Lixin' 'Zhang, Dajun' 'Zhang, Yunan' 'Zhang, Yu' 'Zhang, Qiang' 'Wang, Jian' 'Zeng, Shaoyu' 'Wang, Conggang' _publ_section_title ; Assembly of three Pharmaceutical salts/cocrystals of tetrahydroberberine with sulfophenyl acids: improving the properties by formation of charge-assisted hydrogen bonds ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ00131J _journal_year 2019 _chemical_formula_moiety 'C20 H22 N O4, C7 H5 O6 S' _chemical_formula_sum 'C27 H27 N O10 S' _chemical_formula_weight 557.56 _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-2014/7 _audit_update_record ; 2018-07-29 deposited with the CCDC. 2019-02-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.806(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.6392(4) _cell_length_b 41.6450(17) _cell_length_c 7.5384(4) _cell_measurement_reflns_used 3765 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.4790 _cell_measurement_theta_min 3.6730 _cell_volume 2551.7(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'New Gemini, Dual, Cu at zero, EosS2' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0921 _diffrn_reflns_av_unetI/netI 0.0700 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 28149 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 3.257 _exptl_absorpt_coefficient_mu 0.189 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.451 _exptl_crystal_description block _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.544 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.144 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 356 _refine_ls_number_reflns 4478 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.1094 _refine_ls_R_factor_gt 0.0536 _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^)+(0.0843P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1348 _refine_ls_wR_factor_ref 0.1671 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2749 _reflns_number_total 4478 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj00131j2.cif _cod_data_source_block shelx_CCDC1 _cod_database_code 7058203 _shelx_shelxl_version_number 2014/7 _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 0.738 _shelx_estimated_absorpt_t_max 0.802 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL 1 in P2(1)/c CELL 0.71073 8.6392 41.6450 7.5384 90.000 109.806 90.000 ZERR 33.00 0.0004 0.0017 0.0004 0.000 0.006 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 33 33 33 33 33 MERG 2 OMIT 0.00 50.00 FMAP 2 PLAN 20 SIZE 0.300 0.320 0.420 ACTA BOND $H CONF HTAB HTAB C4 O7 EQIV $1 x, -y+1/2, z+1/2 HTAB C8 O6_$1 EQIV $2 x-1, -y+1/2, z-1/2 HTAB C15 O5_$2 EQIV $3 -x+1, y+1/2, -z+3/2 HTAB C19 O8_$3 HTAB C19 O4 EQIV $4 -x, y+1/2, -z+3/2 HTAB C20 O9_$4 HTAB N1 O7_$1 HTAB N1 S1_$1 HTAB O8 O9 EQIV $5 x-1, y, z HTAB O10 O6_$5 HTAB O10 S1_$5 L.S. 20 WGHT 0.084300 FVAR 0.21431 MOLE 1 C1 1 0.050755 0.280855 0.506068 11.00000 0.03982 0.03995 = 0.05814 0.00061 0.00662 -0.00127 AFIX 43 H1 2 -0.042515 0.293772 0.473636 11.00000 -1.20000 AFIX 0 C2 1 0.039504 0.248381 0.511826 11.00000 0.04317 0.04151 = 0.06410 0.00032 0.00850 -0.00991 C3 1 0.175024 0.228754 0.559071 11.00000 0.05683 0.03268 = 0.04821 -0.00386 0.01420 -0.00634 C4 1 0.329825 0.240743 0.600576 11.00000 0.05014 0.03646 = 0.05294 -0.00055 0.01615 0.00265 AFIX 43 H4 2 0.420877 0.227257 0.630381 11.00000 -1.20000 AFIX 0 C5 1 0.346878 0.274208 0.596707 11.00000 0.04249 0.03652 = 0.04346 0.00120 0.01419 -0.00154 C6 1 0.517403 0.287987 0.643181 11.00000 0.04100 0.04290 = 0.07406 -0.00822 0.02419 0.00120 AFIX 23 H6A 2 0.573365 0.286916 0.778408 11.00000 -1.20000 H6B 2 0.578992 0.275005 0.583409 11.00000 -1.20000 AFIX 0 C7 1 0.515996 0.322251 0.579421 11.00000 0.04660 0.04269 = 0.06621 -0.00335 0.02914 0.00080 AFIX 23 H7A 2 0.625444 0.331373 0.631477 11.00000 -1.20000 H7B 2 0.482460 0.323112 0.443001 11.00000 -1.20000 AFIX 0 C8 1 0.421654 0.376203 0.624966 11.00000 0.04426 0.03238 = 0.05107 0.00278 0.01433 -0.00332 AFIX 23 H8A 2 0.427462 0.380158 0.500571 11.00000 -1.20000 H8B 2 0.526091 0.382583 0.716848 11.00000 -1.20000 AFIX 0 C9 1 0.288166 0.396695 0.650613 11.00000 0.03908 0.03809 = 0.03283 0.00057 0.00880 0.00441 C10 1 0.316679 0.429731 0.670660 11.00000 0.04983 0.03651 = 0.04976 0.00281 0.01872 0.00034 C11 1 0.194374 0.450035 0.689171 11.00000 0.06366 0.03708 = 0.06051 -0.00139 0.02607 0.00452 C12 1 0.047543 0.437037 0.686248 11.00000 0.05407 0.04739 = 0.07356 0.00175 0.02433 0.01358 AFIX 43 H12 2 -0.034376 0.450483 0.698034 11.00000 -1.20000 AFIX 0 C13 1 0.018963 0.404298 0.666097 11.00000 0.04280 0.05160 = 0.06710 0.00028 0.01939 0.00385 AFIX 43 H13 2 -0.081797 0.396089 0.663843 11.00000 -1.20000 AFIX 0 C14 1 0.139207 0.383607 0.649225 11.00000 0.03745 0.03956 = 0.03928 0.00225 0.00815 0.00494 C15 1 0.113808 0.347917 0.636020 11.00000 0.03186 0.04092 = 0.05612 0.00117 0.00964 -0.00143 AFIX 23 H15A 2 -0.000207 0.343513 0.562555 11.00000 -1.20000 H15B 2 0.134449 0.339412 0.761739 11.00000 -1.20000 AFIX 0 C16 1 0.223572 0.330514 0.546837 11.00000 0.03341 0.04106 = 0.04165 -0.00013 0.00203 -0.00114 AFIX 13 H10A 2 0.191653 0.337244 0.414718 11.00000 -1.20000 AFIX 0 C17 1 0.209956 0.294282 0.551349 11.00000 0.04257 0.03280 = 0.04005 -0.00002 0.00732 -0.00275 C18 1 -0.045842 0.197874 0.504319 11.00000 0.07026 0.04304 = 0.10638 -0.01385 0.03313 -0.01810 AFIX 23 H18A 2 -0.095575 0.185494 0.390118 11.00000 -1.20000 H18B 2 -0.078305 0.188369 0.603849 11.00000 -1.20000 AFIX 0 C19 1 0.565514 0.460991 0.783321 11.00000 0.08318 0.11409 = 0.16619 -0.07116 0.05952 -0.04977 AFIX 137 H19A 2 0.592151 0.478646 0.716987 11.00000 -1.50000 H19B 2 0.664615 0.449975 0.854923 11.00000 -1.50000 H19C 2 0.511700 0.468927 0.866962 11.00000 -1.50000 AFIX 0 C20 1 0.124346 0.502982 0.761746 11.00000 0.08922 0.04997 = 0.10254 -0.01059 0.04372 0.01362 AFIX 137 H20A 2 0.015985 0.502496 0.669080 11.00000 -1.50000 H20B 2 0.166336 0.524516 0.774032 11.00000 -1.50000 H20C 2 0.119507 0.495856 0.880865 11.00000 -1.50000 AFIX 0 C21 1 0.083576 0.093581 0.636467 11.00000 0.03694 0.04287 = 0.05422 -0.00258 0.02148 -0.00403 C22 1 0.516849 0.113670 0.668500 11.00000 0.02785 0.03944 = 0.03992 0.00186 0.01169 0.00216 C23 1 0.594104 0.084109 0.725019 11.00000 0.03626 0.05132 = 0.07216 0.01168 0.02053 0.00801 AFIX 43 H23 2 0.706398 0.082119 0.747673 11.00000 -1.20000 AFIX 0 C24 1 0.506070 0.058047 0.747363 11.00000 0.04777 0.04039 = 0.09501 0.01600 0.02934 0.01175 AFIX 43 H24 2 0.558854 0.038476 0.784899 11.00000 -1.20000 AFIX 0 C25 1 0.337033 0.060664 0.714066 11.00000 0.04594 0.03529 = 0.06560 0.00150 0.02867 -0.00500 C26 1 0.259470 0.090289 0.661478 11.00000 0.03339 0.03711 = 0.04918 0.00047 0.01839 -0.00287 C27 1 0.350678 0.116529 0.636822 11.00000 0.02952 0.03723 = 0.03676 0.00026 0.01121 0.00151 AFIX 43 H27 2 0.298742 0.136157 0.598597 11.00000 -1.20000 AFIX 0 N1 3 0.397670 0.341084 0.645705 11.00000 0.03739 0.03533 = 0.04406 0.00233 0.01476 -0.00120 AFIX 13 H1N 2 0.424010 0.336655 0.780412 11.00000 -1.20000 AFIX 0 O1 4 -0.101536 0.230047 0.474459 11.00000 0.05019 0.04599 = 0.12773 -0.00100 0.01460 -0.01453 O2 4 0.127697 0.197053 0.555226 11.00000 0.06203 0.03699 = 0.09570 -0.00241 0.02245 -0.00836 O3 4 0.463167 0.440248 0.656801 11.00000 0.06365 0.05020 = 0.09938 -0.01311 0.04345 -0.01437 O4 4 0.229545 0.482415 0.704517 11.00000 0.08250 0.03360 = 0.12088 -0.00596 0.05214 0.00517 O5 4 0.738118 0.156952 0.818108 11.00000 0.04182 0.07307 = 0.04998 -0.01102 0.00255 -0.01589 O6 4 0.719557 0.135030 0.513658 11.00000 0.03180 0.06225 = 0.06036 0.00110 0.02527 0.00185 O7 4 0.508982 0.170805 0.537894 11.00000 0.03405 0.04112 = 0.05795 0.00659 0.01641 0.00399 O8 4 0.255377 0.034406 0.736157 11.00000 0.06207 0.04160 = 0.11522 0.00971 0.03842 -0.00597 AFIX 147 H8 2 0.157408 0.038681 0.708890 11.00000 -1.50000 AFIX 0 O9 4 -0.003661 0.070903 0.647089 11.00000 0.04255 0.05349 = 0.09565 0.00399 0.03272 -0.01349 O10 4 0.029108 0.123156 0.605128 11.00000 0.03120 0.04728 = 0.09588 0.00111 0.02796 -0.00081 AFIX 147 H10 2 -0.071750 0.123094 0.568418 11.00000 -1.50000 AFIX 0 S1 5 0.630532 0.146861 0.635806 11.00000 0.02475 0.04405 = 0.04514 0.00028 0.01242 -0.00250 HKLF 4 REM 1 in P2(1)/c REM R1 = 0.0536 for 2749 Fo > 4sig(Fo) and 0.1094 for all 4478 data REM 356 parameters refined using 0 restraints END WGHT 0.0843 0.0000 REM Instructions for potential hydrogen bonds HTAB C4 O7 HTAB C8 O6_$1 HTAB C15 O5_$2 HTAB C19 O8_$3 HTAB C19 O4 HTAB C20 O9_$4 HTAB N1 O7_$1 HTAB N1 S1_$1 HTAB O8 O9 HTAB O10 O6_$5 HTAB O10 S1_$5 REM Highest difference peak 0.544, deepest hole -0.594, 1-sigma level 0.144 Q1 1 0.3375 0.1458 0.6871 11.00000 0.05 0.54 Q2 1 0.3204 0.1585 0.5963 11.00000 0.05 0.48 Q3 1 0.2236 0.1438 0.5837 11.00000 0.05 0.46 Q4 1 0.2404 0.1652 0.5984 11.00000 0.05 0.45 Q5 1 0.2053 0.1450 0.5027 11.00000 0.05 0.44 Q6 1 0.1412 0.1584 0.5068 11.00000 0.05 0.40 Q7 1 0.3185 0.1276 0.5776 11.00000 0.05 0.39 Q8 1 0.3586 0.3261 0.2413 11.00000 0.05 0.38 Q9 1 0.2960 0.1739 0.4775 11.00000 0.05 0.37 Q10 1 0.2823 0.3390 0.2631 11.00000 0.05 0.37 Q11 1 -0.2435 0.2543 0.3773 11.00000 0.05 0.37 Q12 1 0.2544 0.3447 0.8671 11.00000 0.05 0.36 Q13 1 0.4386 0.1559 0.7089 11.00000 0.05 0.35 Q14 1 0.2588 0.1297 0.4302 11.00000 0.05 0.35 Q15 1 -0.2233 0.2422 0.2437 11.00000 0.05 0.34 Q16 1 0.7951 0.2643 0.6563 11.00000 0.05 0.33 Q17 1 0.4365 0.3440 0.3395 11.00000 0.05 0.33 Q18 1 0.2165 0.5293 0.6587 11.00000 0.05 0.32 Q19 1 -0.2867 0.4304 0.5647 11.00000 0.05 0.31 Q20 1 -0.2128 0.4434 0.5106 11.00000 0.05 0.31 ; _shelx_res_checksum 25859 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 C1 C 0.0508(4) 0.28086(9) 0.5061(5) 0.0485(10) Uani 1 1 d . . H1 H -0.0425 0.2938 0.4736 0.058 Uiso 1 1 calc R U C2 C 0.0395(4) 0.24838(9) 0.5118(5) 0.0521(10) Uani 1 1 d . . C3 C 0.1750(5) 0.22875(8) 0.5591(5) 0.0468(9) Uani 1 1 d . . C4 C 0.3298(4) 0.24074(8) 0.6006(5) 0.0469(9) Uani 1 1 d . . H4 H 0.4209 0.2273 0.6304 0.056 Uiso 1 1 calc R U C5 C 0.3469(4) 0.27421(8) 0.5967(5) 0.0409(8) Uani 1 1 d . . C6 C 0.5174(4) 0.28799(9) 0.6432(6) 0.0515(10) Uani 1 1 d . . H6A H 0.5734 0.2869 0.7784 0.062 Uiso 1 1 calc R U H6B H 0.5790 0.2750 0.5834 0.062 Uiso 1 1 calc R U C7 C 0.5160(4) 0.32225(8) 0.5794(5) 0.0493(9) Uani 1 1 d . . H7A H 0.6254 0.3314 0.6315 0.059 Uiso 1 1 calc R U H7B H 0.4825 0.3231 0.4430 0.059 Uiso 1 1 calc R U C8 C 0.4217(4) 0.37620(8) 0.6250(5) 0.0430(9) Uani 1 1 d . . H8A H 0.4275 0.3802 0.5006 0.052 Uiso 1 1 calc R U H8B H 0.5261 0.3826 0.7168 0.052 Uiso 1 1 calc R U C9 C 0.2882(4) 0.39670(8) 0.6506(4) 0.0375(8) Uani 1 1 d . . C10 C 0.3167(4) 0.42973(8) 0.6707(5) 0.0449(9) Uani 1 1 d . . C11 C 0.1944(5) 0.45003(9) 0.6892(5) 0.0525(10) Uani 1 1 d . . C12 C 0.0475(5) 0.43704(9) 0.6862(6) 0.0577(11) Uani 1 1 d . . H12 H -0.0344 0.4505 0.6980 0.069 Uiso 1 1 calc R U C13 C 0.0190(4) 0.40430(9) 0.6661(5) 0.0536(10) Uani 1 1 d . . H13 H -0.0818 0.3961 0.6638 0.064 Uiso 1 1 calc R U C14 C 0.1392(4) 0.38361(8) 0.6492(5) 0.0400(8) Uani 1 1 d . . C15 C 0.1138(4) 0.34792(8) 0.6360(5) 0.0443(9) Uani 1 1 d . . H15A H -0.0002 0.3435 0.5626 0.053 Uiso 1 1 calc R U H15B H 0.1344 0.3394 0.7617 0.053 Uiso 1 1 calc R U C16 C 0.2236(4) 0.33051(8) 0.5468(5) 0.0414(9) Uani 1 1 d . . H10A H 0.1917 0.3372 0.4147 0.050 Uiso 1 1 calc R U C17 C 0.2100(4) 0.29428(8) 0.5513(5) 0.0402(8) Uani 1 1 d . . C18 C -0.0458(5) 0.19787(10) 0.5043(7) 0.0724(13) Uani 1 1 d . . H18A H -0.0956 0.1855 0.3901 0.087 Uiso 1 1 calc R U H18B H -0.0783 0.1884 0.6038 0.087 Uiso 1 1 calc R U C19 C 0.5655(6) 0.46099(13) 0.7833(8) 0.117(2) Uani 1 1 d . . H19A H 0.5922 0.4786 0.7170 0.175 Uiso 1 1 calc R U H19B H 0.6646 0.4500 0.8549 0.175 Uiso 1 1 calc R U H19C H 0.5117 0.4689 0.8670 0.175 Uiso 1 1 calc R U C20 C 0.1243(6) 0.50298(10) 0.7617(7) 0.0777(14) Uani 1 1 d . . H20A H 0.0160 0.5025 0.6691 0.117 Uiso 1 1 calc R U H20B H 0.1663 0.5245 0.7740 0.117 Uiso 1 1 calc R U H20C H 0.1195 0.4959 0.8809 0.117 Uiso 1 1 calc R U C21 C 0.0836(4) 0.09358(9) 0.6365(5) 0.0431(9) Uani 1 1 d . . C22 C 0.5168(3) 0.11367(8) 0.6685(4) 0.0357(8) Uani 1 1 d . . C23 C 0.5941(4) 0.08411(9) 0.7250(5) 0.0527(10) Uani 1 1 d . . H23 H 0.7064 0.0821 0.7477 0.063 Uiso 1 1 calc R U C24 C 0.5061(4) 0.05805(9) 0.7474(6) 0.0597(11) Uani 1 1 d . . H24 H 0.5589 0.0385 0.7849 0.072 Uiso 1 1 calc R U C25 C 0.3370(4) 0.06066(8) 0.7141(5) 0.0464(9) Uani 1 1 d . . C26 C 0.2595(4) 0.09029(8) 0.6615(5) 0.0388(8) Uani 1 1 d . . C27 C 0.3507(4) 0.11653(8) 0.6368(4) 0.0345(8) Uani 1 1 d . . H27 H 0.2987 0.1362 0.5986 0.041 Uiso 1 1 calc R U N1 N 0.3977(3) 0.34108(6) 0.6457(4) 0.0387(7) Uani 1 1 d . . H1N H 0.4240 0.3367 0.7804 0.046 Uiso 1 1 calc R U O1 O -0.1015(3) 0.23005(6) 0.4745(5) 0.0786(9) Uani 1 1 d . . O2 O 0.1277(3) 0.19705(6) 0.5552(4) 0.0660(8) Uani 1 1 d . . O3 O 0.4632(3) 0.44025(6) 0.6568(4) 0.0670(8) Uani 1 1 d . . O4 O 0.2295(3) 0.48242(6) 0.7045(4) 0.0745(9) Uani 1 1 d . . O5 O 0.7381(3) 0.15695(6) 0.8181(3) 0.0583(7) Uani 1 1 d . . O6 O 0.7196(2) 0.13503(6) 0.5137(3) 0.0490(7) Uani 1 1 d . . O7 O 0.5090(2) 0.17081(5) 0.5379(3) 0.0442(6) Uani 1 1 d . . O8 O 0.2554(3) 0.03441(6) 0.7362(5) 0.0708(8) Uani 1 1 d . . H8 H 0.1574 0.0387 0.7089 0.106 Uiso 1 1 calc R U O9 O -0.0037(3) 0.07090(6) 0.6471(4) 0.0615(8) Uani 1 1 d . . O10 O 0.0291(3) 0.12316(6) 0.6051(4) 0.0565(7) Uani 1 1 d . . H10 H -0.0718 0.1231 0.5684 0.085 Uiso 1 1 calc R U S1 S 0.63053(9) 0.14686(2) 0.63581(12) 0.0378(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 C1 0.040(2) 0.040(2) 0.058(2) 0.0006(18) 0.0066(17) -0.0013(17) C2 0.043(2) 0.042(2) 0.064(3) 0.0003(19) 0.0085(19) -0.0099(19) C3 0.057(2) 0.033(2) 0.048(2) -0.0039(17) 0.0142(18) -0.0063(19) C4 0.050(2) 0.036(2) 0.053(2) -0.0006(17) 0.0161(18) 0.0027(17) C5 0.0425(19) 0.037(2) 0.043(2) 0.0012(16) 0.0142(16) -0.0015(16) C6 0.041(2) 0.043(2) 0.074(3) -0.0082(19) 0.0242(19) 0.0012(17) C7 0.047(2) 0.043(2) 0.066(3) -0.0034(18) 0.0291(19) 0.0008(17) C8 0.044(2) 0.032(2) 0.051(2) 0.0028(16) 0.0143(17) -0.0033(16) C9 0.0391(19) 0.038(2) 0.0328(19) 0.0006(15) 0.0088(15) 0.0044(16) C10 0.050(2) 0.037(2) 0.050(2) 0.0028(17) 0.0187(18) 0.0003(18) C11 0.064(2) 0.037(2) 0.061(3) -0.0014(18) 0.026(2) 0.005(2) C12 0.054(2) 0.047(3) 0.074(3) 0.002(2) 0.024(2) 0.014(2) C13 0.043(2) 0.052(3) 0.067(3) 0.000(2) 0.0194(19) 0.0039(18) C14 0.0374(19) 0.040(2) 0.039(2) 0.0022(16) 0.0081(15) 0.0049(16) C15 0.0319(18) 0.041(2) 0.056(2) 0.0012(17) 0.0096(16) -0.0014(16) C16 0.0334(18) 0.041(2) 0.042(2) -0.0001(16) 0.0020(15) -0.0011(16) C17 0.0426(19) 0.033(2) 0.040(2) 0.0000(15) 0.0073(16) -0.0027(16) C18 0.070(3) 0.043(3) 0.106(4) -0.014(2) 0.033(3) -0.018(2) C19 0.083(4) 0.114(5) 0.166(6) -0.071(4) 0.060(4) -0.050(3) C20 0.089(3) 0.050(3) 0.103(4) -0.011(2) 0.044(3) 0.014(2) C21 0.0369(19) 0.043(2) 0.054(2) -0.0026(18) 0.0215(17) -0.0040(18) C22 0.0279(17) 0.039(2) 0.040(2) 0.0019(16) 0.0117(15) 0.0022(15) C23 0.0363(19) 0.051(3) 0.072(3) 0.012(2) 0.0205(19) 0.0080(18) C24 0.048(2) 0.040(2) 0.095(3) 0.016(2) 0.029(2) 0.0117(19) C25 0.046(2) 0.035(2) 0.066(3) 0.0015(18) 0.0287(18) -0.0050(17) C26 0.0334(17) 0.037(2) 0.049(2) 0.0005(16) 0.0184(16) -0.0029(16) C27 0.0295(17) 0.037(2) 0.0368(19) 0.0003(15) 0.0112(14) 0.0015(15) N1 0.0374(15) 0.0353(17) 0.0441(17) 0.0023(13) 0.0148(13) -0.0012(13) O1 0.0502(16) 0.0460(18) 0.128(3) -0.0010(17) 0.0146(16) -0.0145(14) O2 0.0620(18) 0.0370(16) 0.096(2) -0.0024(14) 0.0224(15) -0.0084(13) O3 0.0637(17) 0.0502(17) 0.099(2) -0.0131(15) 0.0435(16) -0.0144(14) O4 0.0825(19) 0.0336(16) 0.121(3) -0.0060(15) 0.0521(19) 0.0052(14) O5 0.0418(13) 0.0731(19) 0.0500(16) -0.0110(13) 0.0026(12) -0.0159(13) O6 0.0318(12) 0.0622(17) 0.0604(16) 0.0011(12) 0.0253(11) 0.0019(11) O7 0.0341(12) 0.0411(14) 0.0579(16) 0.0066(11) 0.0164(11) 0.0040(10) O8 0.0621(17) 0.0416(17) 0.115(2) 0.0097(15) 0.0384(18) -0.0060(14) O9 0.0426(14) 0.0535(17) 0.096(2) 0.0040(15) 0.0327(14) -0.0135(13) O10 0.0312(13) 0.0473(17) 0.096(2) 0.0011(14) 0.0280(14) -0.0008(11) S1 0.0248(4) 0.0440(6) 0.0451(5) 0.0003(4) 0.0124(4) -0.0025(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C2 C1 C17 117.4(3) C2 C1 H1 121.3 C17 C1 H1 121.3 C1 C2 C3 122.5(3) C1 C2 O1 127.6(3) C3 C2 O1 109.8(3) C4 C3 C2 121.8(3) C4 C3 O2 128.1(3) C2 C3 O2 110.1(3) C3 C4 C5 117.5(3) C3 C4 H4 121.3 C5 C4 H4 121.3 C17 C5 C4 121.0(3) C17 C5 C6 120.7(3) C4 C5 C6 118.3(3) C7 C6 C5 112.7(3) C7 C6 H6A 109.1 C5 C6 H6A 109.1 C7 C6 H6B 109.1 C5 C6 H6B 109.1 H6A C6 H6B 107.8 N1 C7 C6 108.8(3) N1 C7 H7A 109.9 C6 C7 H7A 109.9 N1 C7 H7B 109.9 C6 C7 H7B 109.9 H7A C7 H7B 108.3 N1 C8 C9 113.8(3) N1 C8 H8A 108.8 C9 C8 H8A 108.8 N1 C8 H8B 108.8 C9 C8 H8B 108.8 H8A C8 H8B 107.7 C14 C9 C10 121.0(3) C14 C9 C8 121.7(3) C10 C9 C8 117.4(3) O3 C10 C11 124.1(3) O3 C10 C9 116.0(3) C11 C10 C9 119.7(3) C12 C11 O4 124.3(3) C12 C11 C10 119.1(3) O4 C11 C10 116.6(3) C11 C12 C13 121.3(4) C11 C12 H12 119.3 C13 C12 H12 119.3 C12 C13 C14 120.7(3) C12 C13 H13 119.7 C14 C13 H13 119.7 C13 C14 C9 118.3(3) C13 C14 C15 121.6(3) C9 C14 C15 120.1(3) C14 C15 C16 113.7(3) C14 C15 H15A 108.8 C16 C15 H15A 108.8 C14 C15 H15B 108.8 C16 C15 H15B 108.8 H15A C15 H15B 107.7 N1 C16 C17 110.7(3) N1 C16 C15 108.1(3) C17 C16 C15 113.6(3) N1 C16 H10A 108.1 C17 C16 H10A 108.1 C15 C16 H10A 108.1 C5 C17 C1 119.8(3) C5 C17 C16 122.5(3) C1 C17 C16 117.7(3) O1 C18 O2 109.7(3) O1 C18 H18A 109.7 O2 C18 H18A 109.7 O1 C18 H18B 109.7 O2 C18 H18B 109.7 H18A C18 H18B 108.2 O3 C19 H19A 109.5 O3 C19 H19B 109.5 H19A C19 H19B 109.5 O3 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 O4 C20 H20A 109.5 O4 C20 H20B 109.5 H20A C20 H20B 109.5 O4 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 O9 C21 O10 122.9(3) O9 C21 C26 123.3(3) O10 C21 C26 113.7(3) C27 C22 C23 119.4(3) C27 C22 S1 120.4(2) C23 C22 S1 120.2(2) C24 C23 C22 120.6(3) C24 C23 H23 119.7 C22 C23 H23 119.7 C23 C24 C25 120.4(3) C23 C24 H24 119.8 C25 C24 H24 119.8 O8 C25 C26 122.2(3) O8 C25 C24 118.3(3) C26 C25 C24 119.4(3) C25 C26 C27 119.4(3) C25 C26 C21 119.6(3) C27 C26 C21 121.0(3) C22 C27 C26 120.7(3) C22 C27 H27 119.6 C26 C27 H27 119.6 C8 N1 C16 112.7(2) C8 N1 C7 110.0(2) C16 N1 C7 111.2(3) C8 N1 H1N 107.5 C16 N1 H1N 107.5 C7 N1 H1N 107.5 C2 O1 C18 105.2(3) C3 O2 C18 105.2(3) C19 O3 C10 122.9(3) C11 O4 C20 118.1(3) C25 O8 H8 109.5 C21 O10 H10 109.5 O5 S1 O7 114.00(15) O5 S1 O6 113.01(14) O7 S1 O6 110.65(14) O5 S1 C22 107.85(15) O7 S1 C22 105.55(13) O6 S1 C22 105.04(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.358(5) C1 C17 1.415(4) C1 H1 0.9300 C2 C3 1.372(5) C2 O1 1.384(4) C3 C4 1.361(5) C3 O2 1.379(4) C4 C5 1.403(5) C4 H4 0.9300 C5 C17 1.393(4) C5 C6 1.508(4) C6 C7 1.504(5) C6 H6A 0.9700 C6 H6B 0.9700 C7 N1 1.502(4) C7 H7A 0.9700 C7 H7B 0.9700 C8 N1 1.493(4) C8 C9 1.499(4) C8 H8A 0.9700 C8 H8B 0.9700 C9 C14 1.394(4) C9 C10 1.397(4) C10 O3 1.376(4) C10 C11 1.397(5) C11 C12 1.372(5) C11 O4 1.379(4) C12 C13 1.385(5) C12 H12 0.9300 C13 C14 1.388(5) C13 H13 0.9300 C14 C15 1.501(4) C15 C16 1.519(5) C15 H15A 0.9700 C15 H15B 0.9700 C16 N1 1.501(4) C16 C17 1.515(5) C16 H10A 0.9800 C18 O1 1.416(4) C18 O2 1.416(5) C18 H18A 0.9700 C18 H18B 0.9700 C19 O3 1.366(5) C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C20 O4 1.418(5) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C21 O9 1.228(4) C21 O10 1.311(4) C21 C26 1.473(5) C22 C27 1.378(4) C22 C23 1.396(4) C22 S1 1.761(3) C23 C24 1.368(5) C23 H23 0.9300 C24 C25 1.400(5) C24 H24 0.9300 C25 O8 1.342(4) C25 C26 1.396(5) C26 C27 1.396(4) C27 H27 0.9300 N1 H1N 0.9800 O5 S1 1.436(2) O6 S1 1.470(2) O7 S1 1.455(2) O8 H8 0.8200 O10 H10 0.8200 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 C4 H4 O7 0.93 2.64 3.406(4) 140.4 . C8 H8B O6 0.97 2.41 3.212(4) 139.9 4_566 C15 H15A O5 0.97 2.38 3.324(4) 163.0 4_465 C19 H19A O8 0.96 2.63 3.452(6) 143.4 2_656 C19 H19C O4 0.96 2.39 2.899(6) 112.4 . C20 H20B O9 0.96 2.57 3.169(5) 120.3 2_556 N1 H1N O7 0.98 1.85 2.826(4) 170.7 4_566 N1 H1N S1 0.98 2.76 3.593(3) 143.8 4_566 O8 H8 O9 0.82 1.87 2.598(4) 146.5 . O10 H10 O6 0.82 1.78 2.573(3) 162.8 1_455 O10 H10 S1 0.82 2.96 3.664(2) 145.9 1_455 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 C17 C1 C2 C3 0.0(6) C17 C1 C2 O1 179.6(4) C1 C2 C3 C4 -1.0(6) O1 C2 C3 C4 179.3(3) C1 C2 C3 O2 179.4(3) O1 C2 C3 O2 -0.3(4) C2 C3 C4 C5 1.1(5) O2 C3 C4 C5 -179.4(3) C3 C4 C5 C17 -0.2(5) C3 C4 C5 C6 179.7(3) C17 C5 C6 C7 -17.1(5) C4 C5 C6 C7 163.0(3) C5 C6 C7 N1 49.3(4) N1 C8 C9 C14 -14.2(4) N1 C8 C9 C10 167.7(3) C14 C9 C10 O3 -175.6(3) C8 C9 C10 O3 2.6(4) C14 C9 C10 C11 -0.2(5) C8 C9 C10 C11 178.0(3) O3 C10 C11 C12 174.7(3) C9 C10 C11 C12 -0.3(5) O3 C10 C11 O4 -3.7(5) C9 C10 C11 O4 -178.7(3) O4 C11 C12 C13 178.5(3) C10 C11 C12 C13 0.3(6) C11 C12 C13 C14 0.4(6) C12 C13 C14 C9 -0.8(5) C12 C13 C14 C15 177.2(3) C10 C9 C14 C13 0.7(5) C8 C9 C14 C13 -177.4(3) C10 C9 C14 C15 -177.3(3) C8 C9 C14 C15 4.5(5) C13 C14 C15 C16 158.3(3) C9 C14 C15 C16 -23.7(4) C14 C15 C16 N1 50.9(4) C14 C15 C16 C17 174.2(3) C4 C5 C17 C1 -0.8(5) C6 C5 C17 C1 179.3(3) C4 C5 C17 C16 179.6(3) C6 C5 C17 C16 -0.3(5) C2 C1 C17 C5 0.9(5) C2 C1 C17 C16 -179.5(3) N1 C16 C17 C5 -15.4(5) C15 C16 C17 C5 -137.3(3) N1 C16 C17 C1 165.0(3) C15 C16 C17 C1 43.1(4) C27 C22 C23 C24 0.6(5) S1 C22 C23 C24 -178.8(3) C22 C23 C24 C25 -0.1(6) C23 C24 C25 O8 179.4(4) C23 C24 C25 C26 -1.3(6) O8 C25 C26 C27 -178.6(3) C24 C25 C26 C27 2.1(5) O8 C25 C26 C21 2.6(5) C24 C25 C26 C21 -176.7(3) O9 C21 C26 C25 -5.1(5) O10 C21 C26 C25 173.7(3) O9 C21 C26 C27 176.1(3) O10 C21 C26 C27 -5.0(5) C23 C22 C27 C26 0.3(5) S1 C22 C27 C26 179.7(2) C25 C26 C27 C22 -1.7(5) C21 C26 C27 C22 177.1(3) C9 C8 N1 C16 43.6(4) C9 C8 N1 C7 168.4(3) C17 C16 N1 C8 173.0(3) C15 C16 N1 C8 -62.0(4) C17 C16 N1 C7 48.8(4) C15 C16 N1 C7 173.9(3) C6 C7 N1 C8 166.8(3) C6 C7 N1 C16 -67.5(4) C1 C2 O1 C18 -178.7(4) C3 C2 O1 C18 1.0(4) O2 C18 O1 C2 -1.3(5) C4 C3 O2 C18 180.0(4) C2 C3 O2 C18 -0.5(4) O1 C18 O2 C3 1.1(5) C11 C10 O3 C19 52.4(6) C9 C10 O3 C19 -132.4(4) C12 C11 O4 C20 14.4(6) C10 C11 O4 C20 -167.3(4) C27 C22 S1 O5 110.2(3) C23 C22 S1 O5 -70.4(3) C27 C22 S1 O7 -12.0(3) C23 C22 S1 O7 167.4(3) C27 C22 S1 O6 -129.0(3) C23 C22 S1 O6 50.4(3)