#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238857.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2238857 loop_ _publ_author_name 'Corvalan, Carolina H.' 'Vega, Daniel R.' _publ_section_title ; Venlafaxine besylate monohydrate ; _journal_coeditor_code GG2130 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1737 _journal_page_last o1738 _journal_paper_doi 10.1107/S1600536813027542 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C17 H28 N O2 +, C6 H5 O3 S -, H2 O' _chemical_formula_moiety 'C17 H28 N O2 +, C6 H5 O3 S -, H2 O' _chemical_formula_sum 'C23 H35 N O6 S' _chemical_formula_weight 453.58 _chemical_name_systematic ; [2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]dimethylazanium benzenesulfonate monohydrate ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 72.074(4) _cell_angle_beta 70.108(4) _cell_angle_gamma 63.889(5) _cell_formula_units_Z 2 _cell_length_a 10.1163(5) _cell_length_b 10.2176(4) _cell_length_c 13.8162(6) _cell_measurement_reflns_used 3716 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8327 _cell_measurement_theta_min 3.7773 _cell_volume 1184.53(11) _computing_cell_refinement 'CrysAlis PRO (Agilent, 2010)' _computing_data_collection 'CrysAlis PRO (Agilent, 2010)' _computing_data_reduction 'CrysAlis PRO (Agilent, 2010)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX (Farrugia, 2012) and PLATON (Spek, 2009)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1158 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.865 _diffrn_measurement_device_type 'Agilent Xcalibur (Eos, Gemini)' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 10063 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.84 _diffrn_reflns_theta_min 3.79 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2010)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.536 _refine_diff_density_min -0.435 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 5366 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0534 _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^)+(0.0896P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1511 _refine_ls_wR_factor_ref 0.1631 _reflns_number_gt 3072 _reflns_number_total 5366 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL Besilato_Ven_Mo in P-1 CELL 0.71073 10.116323 10.217596 13.816183 72.0742 70.1079 63.8888 ZERR 2.00 0.000516 0.000394 0.000637 0.0039 0.0044 0.0045 LATT 1 SFAC C H N O S UNIT 46 70 2 12 2 L.S. 10 ACTA 50 BOND $H FMAP 2 PLAN 20 CONF SIZE 0.10 0.30 0.70 HTAB TEMP 20.00 WGHT 0.089600 FVAR 7.59597 C1 1 0.149827 0.478898 0.264369 11.00000 0.04124 0.04546 = 0.03617 -0.00532 -0.01090 -0.01811 C2 1 0.114661 0.629767 0.225705 11.00000 0.04882 0.04396 = 0.05199 -0.00699 -0.01562 -0.02193 AFIX 43 H2 2 0.165612 0.677095 0.238507 11.00000 -1.20000 AFIX 0 C3 1 0.006255 0.710776 0.168935 11.00000 0.05253 0.03865 = 0.05438 -0.00122 -0.01569 -0.02020 AFIX 43 H3 2 -0.014748 0.811592 0.143559 11.00000 -1.20000 AFIX 0 C4 1 -0.071479 0.643440 0.149414 11.00000 0.04337 0.04997 = 0.03887 -0.00115 -0.01331 -0.01795 C5 1 -0.040246 0.494105 0.187630 11.00000 0.05071 0.05214 = 0.05166 -0.00615 -0.01702 -0.02755 AFIX 43 H5 2 -0.092315 0.447614 0.175182 11.00000 -1.20000 AFIX 0 C6 1 0.068640 0.414258 0.244385 11.00000 0.04970 0.03981 = 0.05338 -0.00281 -0.01598 -0.01937 AFIX 43 H6 2 0.088502 0.313690 0.270205 11.00000 -1.20000 AFIX 0 C7 1 0.271536 0.392720 0.325306 11.00000 0.04652 0.04499 = 0.03877 -0.00499 -0.01243 -0.01999 AFIX 13 H7 2 0.284193 0.466433 0.349262 11.00000 -1.20000 AFIX 0 C8 1 0.430060 0.308888 0.258292 11.00000 0.04214 0.04219 = 0.03213 -0.00099 -0.01227 -0.01924 C9 1 0.484498 0.420196 0.169146 11.00000 0.05195 0.04311 = 0.03679 0.00352 -0.01740 -0.02294 AFIX 23 H9A 2 0.412027 0.472058 0.125669 11.00000 -1.20000 H9B 2 0.487885 0.493082 0.198657 11.00000 -1.20000 AFIX 0 C10 1 0.639073 0.347773 0.101634 11.00000 0.05620 0.06106 = 0.04070 0.00133 -0.00853 -0.02983 AFIX 23 H10A 2 0.713788 0.305178 0.143118 11.00000 -1.20000 H10B 2 0.665493 0.422430 0.044559 11.00000 -1.20000 AFIX 0 C11 1 0.643553 0.227232 0.057068 11.00000 0.06758 0.07502 = 0.04406 -0.01851 0.00266 -0.03095 AFIX 23 H11A 2 0.745961 0.178158 0.018425 11.00000 -1.20000 H11B 2 0.577700 0.271037 0.008996 11.00000 -1.20000 AFIX 0 C12 1 0.592050 0.114170 0.145131 11.00000 0.08256 0.05509 = 0.05539 -0.02101 -0.00634 -0.02618 AFIX 23 H12A 2 0.664531 0.062972 0.188614 11.00000 -1.20000 H12B 2 0.589596 0.041071 0.115312 11.00000 -1.20000 AFIX 0 C13 1 0.435282 0.187585 0.212831 11.00000 0.06283 0.04800 = 0.04624 -0.00608 -0.01191 -0.02793 AFIX 23 H13A 2 0.408341 0.112960 0.269658 11.00000 -1.20000 H13B 2 0.361160 0.230352 0.170863 11.00000 -1.20000 AFIX 0 C14 1 0.218924 0.292817 0.423431 11.00000 0.05456 0.05466 = 0.04277 -0.00294 -0.01360 -0.02691 AFIX 23 H14A 2 0.112052 0.343626 0.452941 11.00000 -1.20000 H14B 2 0.230257 0.203832 0.404611 11.00000 -1.20000 AFIX 0 C15 1 0.263009 0.369596 0.560371 11.00000 0.07496 0.05387 = 0.05767 -0.01552 -0.01522 -0.02565 AFIX 33 H15A 2 0.322573 0.334861 0.610886 11.00000 -1.20000 H15B 2 0.157395 0.399397 0.595509 11.00000 -1.20000 H15C 2 0.281743 0.452750 0.510847 11.00000 -1.20000 AFIX 0 C16 1 0.288839 0.115878 0.581099 11.00000 0.08412 0.05277 = 0.05470 0.00539 -0.01563 -0.03229 AFIX 33 H16A 2 0.317109 0.038083 0.544313 11.00000 -1.20000 H16B 2 0.185382 0.139285 0.620579 11.00000 -1.20000 H16C 2 0.353545 0.083706 0.627860 11.00000 -1.20000 AFIX 0 C17 1 -0.261024 0.669075 0.073117 11.00000 0.06871 0.08948 = 0.08342 0.00458 -0.04394 -0.03601 AFIX 33 H17A 2 -0.331507 0.742977 0.033101 11.00000 -1.20000 H17B 2 -0.315457 0.628577 0.138448 11.00000 -1.20000 H17C 2 -0.192799 0.591266 0.034434 11.00000 -1.20000 AFIX 0 N1 3 0.305000 0.249360 0.504835 11.00000 0.04047 0.04282 = 0.03282 -0.00339 -0.00554 -0.01273 H1 2 0.390127 0.232259 0.474584 11.00000 -1.20000 O1 4 -0.177616 0.734409 0.092784 11.00000 0.06190 0.06250 = 0.06806 0.00676 -0.03672 -0.02322 O2 4 0.531639 0.234899 0.327293 11.00000 0.04551 0.04387 = 0.03912 0.00301 -0.01771 -0.01749 H2A 2 0.569322 0.291423 0.326265 11.00000 -1.50000 S1B 5 0.314363 0.789023 0.404282 11.00000 0.07317 0.04423 = 0.07738 -0.00731 -0.04208 -0.01370 C1B 1 0.201605 1.017073 0.131558 11.00000 0.09945 0.06228 = 0.04545 -0.00671 -0.01228 -0.03561 AFIX 43 H1B 2 0.250153 1.026331 0.060717 11.00000 -1.20000 AFIX 0 C2B 1 0.283442 0.923739 0.204715 11.00000 0.05731 0.05315 = 0.06620 -0.01818 -0.00674 -0.01844 AFIX 43 H2B 2 0.386922 0.870896 0.183325 11.00000 -1.20000 AFIX 0 C3B 1 0.211506 0.908874 0.309763 11.00000 0.05373 0.03335 = 0.05138 -0.00979 -0.01805 -0.01769 C4B 1 0.058454 0.988899 0.339743 11.00000 0.05493 0.05556 = 0.04988 -0.01241 -0.00964 -0.01690 AFIX 43 H4B 2 0.008632 0.980758 0.410347 11.00000 -1.20000 AFIX 0 C5B 1 -0.020686 1.081022 0.264945 11.00000 0.05604 0.06240 = 0.07416 -0.01030 -0.02445 -0.00981 AFIX 43 H5B 2 -0.124363 1.133874 0.285268 11.00000 -1.20000 AFIX 0 C6B 1 0.051367 1.095338 0.161791 11.00000 0.08322 0.05698 = 0.06354 -0.00389 -0.03428 -0.02002 AFIX 43 H6B 2 -0.002655 1.159031 0.111878 11.00000 -1.20000 AFIX 0 O1B 4 0.378650 0.868532 0.429701 11.00000 0.11215 0.07147 = 0.09685 -0.00560 -0.06103 -0.04283 O2B 4 0.204592 0.743470 0.492932 11.00000 0.12693 0.13614 = 0.11518 0.07227 -0.07550 -0.08170 O3B 4 0.421116 0.665702 0.358979 11.00000 0.15409 0.08347 = 0.18349 -0.06873 -0.12239 0.05016 O1W 4 0.661807 0.406286 0.338009 11.00000 0.06238 0.05950 = 0.06753 -0.01239 -0.02745 -0.02083 H1WA 2 0.699769 0.357386 0.393237 11.00000 -1.40000 H1WB 2 0.590296 0.480010 0.360317 11.00000 -1.40000 HKLF 4 REM 09_12_01_Besilato_Ven_Mo in P-1 REM R1 = 0.0534 for 3072 Fo > 4sig(Fo) and 0.0962 for all 5366 data REM 292 parameters refined using 0 restraints END WGHT 0.0887 0.0000 REM Highest difference peak 0.536, deepest hole -0.435, 1-sigma level 0.043 Q1 1 0.4235 0.7685 0.3570 11.00000 0.05 0.54 Q2 1 0.2141 0.8212 0.5032 11.00000 0.05 0.45 Q3 1 0.2398 0.3991 0.4167 11.00000 0.05 0.44 Q4 1 0.2941 0.6902 0.4392 11.00000 0.05 0.42 Q5 1 0.5025 0.7286 0.3109 11.00000 0.05 0.39 Q6 1 0.3810 0.6582 0.3655 11.00000 0.05 0.37 Q7 1 0.2660 0.3152 0.3293 11.00000 0.05 0.29 Q8 1 0.1769 0.7367 0.5148 11.00000 0.05 0.21 Q9 1 0.4630 0.8444 0.3517 11.00000 0.05 0.19 Q10 1 0.4636 0.3637 0.2155 11.00000 0.05 0.19 Q11 1 0.1423 0.4358 0.2397 11.00000 0.05 0.18 Q12 1 0.5211 0.1465 0.1950 11.00000 0.05 0.17 Q13 1 0.1599 0.5431 0.2272 11.00000 0.05 0.17 Q14 1 -0.0790 0.5798 0.1884 11.00000 0.05 0.16 Q15 1 0.2002 0.4413 0.2993 11.00000 0.05 0.16 Q16 1 0.1215 0.5581 0.2478 11.00000 0.05 0.16 Q17 1 -0.0426 0.5583 0.1567 11.00000 0.05 0.16 Q18 1 0.1602 0.9622 0.3350 11.00000 0.05 0.15 Q19 1 0.0187 0.7436 0.1655 11.00000 0.05 0.15 Q20 1 0.2544 0.8587 0.3534 11.00000 0.05 0.15 ; _cod_data_source_file gg2130.cif _cod_data_source_block I _cod_original_formula_sum 'C23 H35 N1 O6 S1' _cod_database_code 2238857 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity C C1 0.1498(2) 0.4789(2) 0.26437(16) 0.0404(5) Uani d . 1 1 C C2 0.1147(3) 0.6298(2) 0.22570(18) 0.0460(5) Uani d . 1 1 H H2 0.1656 0.6771 0.2385 0.055 Uiso calc R 1 1 C C3 0.0063(3) 0.7108(2) 0.16894(18) 0.0484(6) Uani d . 1 1 H H3 -0.0147 0.8116 0.1436 0.058 Uiso calc R 1 1 C C4 -0.0715(3) 0.6434(2) 0.14941(17) 0.0447(5) Uani d . 1 1 C C5 -0.0402(3) 0.4941(2) 0.18763(18) 0.0479(6) Uani d . 1 1 H H5 -0.0923 0.4476 0.1752 0.057 Uiso calc R 1 1 C C6 0.0686(3) 0.4143(2) 0.24438(18) 0.0471(6) Uani d . 1 1 H H6 0.0885 0.3137 0.2702 0.057 Uiso calc R 1 1 C C7 0.2715(3) 0.3927(2) 0.32531(16) 0.0424(5) Uani d . 1 1 H H7 0.2842 0.4664 0.3493 0.051 Uiso calc R 1 1 C C8 0.4301(2) 0.3089(2) 0.25829(15) 0.0381(5) Uani d . 1 1 C C9 0.4845(3) 0.4202(2) 0.16915(16) 0.0429(5) Uani d . 1 1 H H9A 0.4120 0.4721 0.1257 0.051 Uiso calc R 1 1 H H9B 0.4879 0.4931 0.1987 0.051 Uiso calc R 1 1 C C10 0.6391(3) 0.3478(3) 0.10163(18) 0.0533(6) Uani d . 1 1 H H10A 0.7138 0.3052 0.1431 0.064 Uiso calc R 1 1 H H10B 0.6655 0.4224 0.0446 0.064 Uiso calc R 1 1 C C11 0.6436(3) 0.2272(3) 0.05707(19) 0.0633(7) Uani d . 1 1 H H11A 0.7460 0.1782 0.0184 0.076 Uiso calc R 1 1 H H11B 0.5777 0.2710 0.0090 0.076 Uiso calc R 1 1 C C12 0.5921(3) 0.1142(3) 0.1451(2) 0.0644(7) Uani d . 1 1 H H12A 0.6645 0.0630 0.1886 0.077 Uiso calc R 1 1 H H12B 0.5896 0.0411 0.1153 0.077 Uiso calc R 1 1 C C13 0.4353(3) 0.1876(2) 0.21283(18) 0.0506(6) Uani d . 1 1 H H13A 0.4083 0.1130 0.2697 0.061 Uiso calc R 1 1 H H13B 0.3612 0.2304 0.1709 0.061 Uiso calc R 1 1 C C14 0.2189(3) 0.2928(3) 0.42343(17) 0.0492(6) Uani d . 1 1 H H14A 0.1121 0.3436 0.4529 0.059 Uiso calc R 1 1 H H14B 0.2303 0.2038 0.4046 0.059 Uiso calc R 1 1 C C15 0.2630(3) 0.3696(3) 0.5604(2) 0.0605(7) Uani d . 1 1 H H15A 0.3226 0.3349 0.6109 0.073 Uiso calc R 1 1 H H15B 0.1574 0.3994 0.5955 0.073 Uiso calc R 1 1 H H15C 0.2817 0.4528 0.5108 0.073 Uiso calc R 1 1 C C16 0.2888(4) 0.1159(3) 0.5811(2) 0.0655(7) Uani d . 1 1 H H16A 0.3171 0.0381 0.5443 0.079 Uiso calc R 1 1 H H16B 0.1854 0.1393 0.6206 0.079 Uiso calc R 1 1 H H16C 0.3535 0.0837 0.6279 0.079 Uiso calc R 1 1 C C17 -0.2610(3) 0.6691(3) 0.0731(2) 0.0761(9) Uani d . 1 1 H H17A -0.3315 0.7430 0.0331 0.091 Uiso calc R 1 1 H H17B -0.3155 0.6286 0.1384 0.091 Uiso calc R 1 1 H H17C -0.1928 0.5913 0.0344 0.091 Uiso calc R 1 1 N N1 0.3050(2) 0.2494(2) 0.50483(14) 0.0416(5) Uani d . 1 1 H H1 0.390(3) 0.232(3) 0.4746(19) 0.050 Uiso d . 1 1 O O1 -0.1776(2) 0.73441(18) 0.09278(14) 0.0630(5) Uani d . 1 1 O O2 0.53164(17) 0.23490(16) 0.32729(11) 0.0431(4) Uani d . 1 1 H H2A 0.569(3) 0.291(3) 0.326(2) 0.065 Uiso d . 1 1 S S1B 0.31436(9) 0.78902(7) 0.40428(6) 0.0623(2) Uani d . 1 1 C C1B 0.2016(4) 1.0171(3) 0.1316(2) 0.0693(8) Uani d . 1 1 H H1B 0.2502 1.0263 0.0607 0.083 Uiso calc R 1 1 C C2B 0.2834(3) 0.9237(3) 0.2047(2) 0.0603(7) Uani d . 1 1 H H2B 0.3869 0.8709 0.1833 0.072 Uiso calc R 1 1 C C3B 0.2115(3) 0.9089(2) 0.30976(18) 0.0436(5) Uani d . 1 1 C C4B 0.0585(3) 0.9889(3) 0.3397(2) 0.0551(6) Uani d . 1 1 H H4B 0.0086 0.9808 0.4103 0.066 Uiso calc R 1 1 C C5B -0.0207(3) 1.0810(3) 0.2649(2) 0.0671(7) Uani d . 1 1 H H5B -0.1244 1.1339 0.2853 0.080 Uiso calc R 1 1 C C6B 0.0514(4) 1.0953(3) 0.1618(2) 0.0675(8) Uani d . 1 1 H H6B -0.0027 1.1590 0.1119 0.081 Uiso calc R 1 1 O O1B 0.3786(3) 0.8685(2) 0.42970(16) 0.0827(7) Uani d . 1 1 O O2B 0.2046(3) 0.7435(3) 0.4929(2) 0.1248(11) Uani d . 1 1 O O3B 0.4211(3) 0.6657(3) 0.3590(3) 0.1424(13) Uani d . 1 1 O O1W 0.6618(2) 0.4063(2) 0.33801(15) 0.0604(5) Uani d . 1 1 H H1WA 0.700(4) 0.357(3) 0.393(2) 0.085 Uiso d . 1 1 H H1WB 0.590(4) 0.480(3) 0.360(2) 0.085 Uiso d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0412(13) 0.0455(12) 0.0362(11) -0.0181(10) -0.0109(10) -0.0053(9) C2 0.0488(14) 0.0440(12) 0.0520(13) -0.0219(11) -0.0156(11) -0.0070(10) C3 0.0525(15) 0.0387(11) 0.0544(14) -0.0202(11) -0.0157(12) -0.0012(10) C4 0.0434(13) 0.0500(12) 0.0389(12) -0.0179(10) -0.0133(10) -0.0012(9) C5 0.0507(14) 0.0521(13) 0.0517(13) -0.0275(11) -0.0170(11) -0.0062(10) C6 0.0497(14) 0.0398(11) 0.0534(14) -0.0194(11) -0.0160(11) -0.0028(10) C7 0.0465(14) 0.0450(11) 0.0388(12) -0.0200(10) -0.0124(10) -0.0050(9) C8 0.0421(13) 0.0422(11) 0.0321(10) -0.0192(10) -0.0123(9) -0.0010(8) C9 0.0520(14) 0.0431(11) 0.0368(11) -0.0229(10) -0.0174(10) 0.0035(9) C10 0.0562(16) 0.0611(14) 0.0407(13) -0.0298(13) -0.0085(11) 0.0013(11) C11 0.0676(19) 0.0750(17) 0.0441(14) -0.0310(14) 0.0027(13) -0.0185(12) C12 0.083(2) 0.0551(14) 0.0554(16) -0.0262(14) -0.0063(14) -0.0210(12) C13 0.0628(16) 0.0480(12) 0.0462(13) -0.0279(12) -0.0119(12) -0.0061(10) C14 0.0546(15) 0.0547(13) 0.0428(13) -0.0269(12) -0.0136(11) -0.0029(10) C15 0.0750(19) 0.0539(14) 0.0577(15) -0.0256(13) -0.0152(14) -0.0155(12) C16 0.084(2) 0.0528(14) 0.0547(15) -0.0323(14) -0.0156(14) 0.0054(12) C17 0.069(2) 0.089(2) 0.083(2) -0.0360(17) -0.0439(17) 0.0046(16) N1 0.0405(11) 0.0428(10) 0.0328(10) -0.0127(9) -0.0055(8) -0.0034(7) O1 0.0619(11) 0.0625(10) 0.0681(11) -0.0232(9) -0.0367(9) 0.0068(8) O2 0.0455(9) 0.0439(8) 0.0391(8) -0.0175(7) -0.0177(7) 0.0030(6) S1B 0.0732(5) 0.0442(3) 0.0774(5) -0.0137(3) -0.0421(4) -0.0073(3) C1B 0.099(2) 0.0623(16) 0.0455(15) -0.0356(17) -0.0123(15) -0.0067(12) C2B 0.0573(17) 0.0531(14) 0.0662(18) -0.0184(12) -0.0067(14) -0.0182(13) C3B 0.0537(15) 0.0333(10) 0.0514(14) -0.0177(10) -0.0181(11) -0.0098(9) C4B 0.0549(16) 0.0556(14) 0.0499(14) -0.0169(12) -0.0096(12) -0.0124(11) C5B 0.0560(17) 0.0624(16) 0.074(2) -0.0098(13) -0.0244(15) -0.0103(14) C6B 0.083(2) 0.0570(15) 0.0635(18) -0.0200(15) -0.0343(16) -0.0039(13) O1B 0.1121(18) 0.0715(12) 0.0969(16) -0.0428(12) -0.0610(14) -0.0056(11) O2B 0.127(2) 0.136(2) 0.1152(19) -0.0817(19) -0.0755(18) 0.0723(17) O3B 0.154(3) 0.0835(15) 0.183(3) 0.0502(15) -0.122(2) -0.0687(17) O1W 0.0624(13) 0.0595(11) 0.0675(12) -0.0208(9) -0.0275(10) -0.0124(9) 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 0 '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 0.006 '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 C6 116.87(19) C2 C1 C7 120.05(18) C6 C1 C7 123.08(18) C3 C2 C1 121.5(2) C3 C2 H2 119.2 C1 C2 H2 119.2 C2 C3 C4 120.4(2) C2 C3 H3 119.8 C4 C3 H3 119.8 O1 C4 C5 124.9(2) O1 C4 C3 115.6(2) C5 C4 C3 119.5(2) C6 C5 C4 119.51(19) C6 C5 H5 120.2 C4 C5 H5 120.2 C5 C6 C1 122.22(19) C5 C6 H6 118.9 C1 C6 H6 118.9 C1 C7 C14 110.96(18) C1 C7 C8 114.09(16) C14 C7 C8 112.73(18) C1 C7 H7 106.1 C14 C7 H7 106.1 C8 C7 H7 106.1 O2 C8 C13 105.98(16) O2 C8 C9 110.41(16) C13 C8 C9 109.26(17) O2 C8 C7 106.88(15) C13 C8 C7 114.63(18) C9 C8 C7 109.58(17) C10 C9 C8 112.83(18) C10 C9 H9A 109.0 C8 C9 H9A 109.0 C10 C9 H9B 109.0 C8 C9 H9B 109.0 H9A C9 H9B 107.8 C9 C10 C11 111.7(2) C9 C10 H10A 109.3 C11 C10 H10A 109.3 C9 C10 H10B 109.3 C11 C10 H10B 109.3 H10A C10 H10B 107.9 C10 C11 C12 110.1(2) C10 C11 H11A 109.6 C12 C11 H11A 109.6 C10 C11 H11B 109.6 C12 C11 H11B 109.6 H11A C11 H11B 108.1 C11 C12 C13 111.7(2) C11 C12 H12A 109.3 C13 C12 H12A 109.3 C11 C12 H12B 109.3 C13 C12 H12B 109.3 H12A C12 H12B 107.9 C12 C13 C8 111.8(2) C12 C13 H13A 109.3 C8 C13 H13A 109.3 C12 C13 H13B 109.3 C8 C13 H13B 109.3 H13A C13 H13B 107.9 N1 C14 C7 113.01(18) N1 C14 H14A 109.0 C7 C14 H14A 109.0 N1 C14 H14B 109.0 C7 C14 H14B 109.0 H14A C14 H14B 107.8 N1 C15 H15A 109.5 N1 C15 H15B 109.5 H15A C15 H15B 109.5 N1 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 N1 C16 H16A 109.5 N1 C16 H16B 109.5 H16A C16 H16B 109.5 N1 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 O1 C17 H17A 109.5 O1 C17 H17B 109.5 H17A C17 H17B 109.5 O1 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C15 N1 C16 110.07(18) C15 N1 C14 113.67(18) C16 N1 C14 110.92(19) C15 N1 H1 105.9(18) C16 N1 H1 110.0(18) C14 N1 H1 106.1(18) C4 O1 C17 116.91(19) C8 O2 H2A 108.2(19) O3B S1B O1B 114.29(16) O3B S1B O2B 109.48(19) O1B S1B O2B 112.99(15) O3B S1B C3B 105.89(13) O1B S1B C3B 107.97(10) O2B S1B C3B 105.58(12) C6B C1B C2B 120.6(3) C6B C1B H1B 119.7 C2B C1B H1B 119.7 C1B C2B C3B 119.8(3) C1B C2B H2B 120.1 C3B C2B H2B 120.1 C4B C3B C2B 119.1(2) C4B C3B S1B 120.50(19) C2B C3B S1B 120.4(2) C3B C4B C5B 119.8(2) C3B C4B H4B 120.1 C5B C4B H4B 120.1 C6B C5B C4B 120.5(3) C6B C5B H5B 119.7 C4B C5B H5B 119.7 C1B C6B C5B 120.0(3) C1B C6B H6B 120.0 C5B C6B H6B 120.0 H1WA O1W H1WB 102(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.388(3) C1 C6 1.390(3) C1 C7 1.515(3) C2 C3 1.375(3) C2 H2 0.9300 C3 C4 1.378(3) C3 H3 0.9300 C4 O1 1.369(2) C4 C5 1.378(3) C5 C6 1.377(3) C5 H5 0.9300 C6 H6 0.9300 C7 C14 1.516(3) C7 C8 1.559(3) C7 H7 0.9800 C8 O2 1.441(2) C8 C13 1.527(3) C8 C9 1.530(3) C9 C10 1.509(3) C9 H9A 0.9700 C9 H9B 0.9700 C10 C11 1.516(3) C10 H10A 0.9700 C10 H10B 0.9700 C11 C12 1.523(3) C11 H11A 0.9700 C11 H11B 0.9700 C12 C13 1.526(4) C12 H12A 0.9700 C12 H12B 0.9700 C13 H13A 0.9700 C13 H13B 0.9700 C14 N1 1.496(3) C14 H14A 0.9700 C14 H14B 0.9700 C15 N1 1.476(3) C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C16 N1 1.480(3) C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 O1 1.412(3) C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 N1 H1 0.78(3) O2 H2A 0.81(2) S1B O3B 1.405(2) S1B O1B 1.4150(18) S1B O2B 1.459(3) S1B C3B 1.762(2) C1B C6B 1.352(4) C1B C2B 1.378(4) C1B H1B 0.9300 C2B C3B 1.379(3) C2B H2B 0.9300 C3B C4B 1.377(3) C4B C5B 1.377(3) C4B H4B 0.9300 C5B C6B 1.357(4) C5B H5B 0.9300 C6B H6B 0.9300 O1W H1WA 0.88(3) O1W H1WB 0.84(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H2A O1W 1_555 0.81(3) 1.87(3) 2.673(3) 173(3) O1W H1WB O3B 1_555 0.83(3) 1.92(3) 2.711(4) 159(3) O1W H1WA O2B 2_666 0.88(3) 1.91(3) 2.785(4) 175(3) N1 H1 O2 1_555 0.78(3) 2.05(3) 2.719(2) 143(3) C15 H15C O2B 1_555 0.96 2.68 3.468(4) 140 C16 H16A O1B 1_545 0.96 2.44 3.395(4) 172 C2 H2 Cg1 1_555 0.93 3.17 3.928 140 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 C6 C1 C2 C3 -1.0(3) C7 C1 C2 C3 179.1(2) C1 C2 C3 C4 0.4(4) C2 C3 C4 O1 179.6(2) C2 C3 C4 C5 0.3(4) O1 C4 C5 C6 -179.5(2) C3 C4 C5 C6 -0.3(4) C4 C5 C6 C1 -0.4(4) C2 C1 C6 C5 1.0(3) C7 C1 C6 C5 -179.1(2) C2 C1 C7 C14 134.3(2) C6 C1 C7 C14 -45.6(3) C2 C1 C7 C8 -97.0(2) C6 C1 C7 C8 83.1(3) C1 C7 C8 O2 179.41(16) C14 C7 C8 O2 -52.9(2) C1 C7 C8 C13 -63.5(2) C14 C7 C8 C13 64.3(2) C1 C7 C8 C9 59.8(2) C14 C7 C8 C9 -172.50(17) O2 C8 C9 C10 61.5(2) C13 C8 C9 C10 -54.7(2) C7 C8 C9 C10 178.92(17) C8 C9 C10 C11 56.0(2) C9 C10 C11 C12 -55.1(3) C10 C11 C12 C13 55.6(3) C11 C12 C13 C8 -56.5(3) O2 C8 C13 C12 -64.4(2) C9 C8 C13 C12 54.5(2) C7 C8 C13 C12 177.97(18) C1 C7 C14 N1 -158.74(18) C8 C7 C14 N1 71.9(2) C7 C14 N1 C15 74.7(2) C7 C14 N1 C16 -160.7(2) C5 C4 O1 C17 0.4(4) C3 C4 O1 C17 -178.9(2) C6B C1B C2B C3B 0.5(4) C1B C2B C3B C4B -0.4(4) C1B C2B C3B S1B 179.60(18) O3B S1B C3B C4B 143.1(2) O1B S1B C3B C4B -94.1(2) O2B S1B C3B C4B 27.0(2) O3B S1B C3B C2B -36.9(2) O1B S1B C3B C2B 85.9(2) O2B S1B C3B C2B -153.0(2) C2B C3B C4B C5B 0.6(4) S1B C3B C4B C5B -179.39(18) C3B C4B C5B C6B -1.0(4) C2B C1B C6B C5B -0.8(4) C4B C5B C6B C1B 1.0(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086206