#------------------------------------------------------------------------------ #$Date: 2019-04-20 03:49:12 +0300 (Sat, 20 Apr 2019) $ #$Revision: 214712 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058316.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_7058316 loop_ _publ_author_name 'Tanase, Constantin I.' 'Cocu, Florea G.' 'Draghici, Constantin' 'Hanganu, Anamaria' 'Pintilie, Lucia' 'Maganu, Maria' 'MUNTEANU, CRISTIAN V.A.' 'Sova, Sergiu' _publ_section_title ; Secondary Compounds in the Catalytic Hydrogenation of Enone and Allylic Alcohol Prostaglandin Intermediates: Isolation, Characterization, X-Ray Crystallography. ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ01186B _journal_year 2019 _chemical_absolute_configuration unk _chemical_formula_moiety 'C17 H22 O4' _chemical_formula_sum 'C17 H22 O4' _chemical_formula_weight 290.34 _space_group_crystal_system orthorhombic _space_group_IT_number 18 _space_group_name_Hall 'P 2 2ab' _space_group_name_H-M_alt 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_space_group_name_H-M 'P 21 21 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-12-04 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-12-04 deposited with the CCDC. 2019-04-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6481(17) _cell_length_b 30.186(4) _cell_length_c 6.7702(6) _cell_measurement_reflns_used 1216 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.7040 _cell_measurement_theta_min 2.6690 _cell_volume 1563.0(4) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0797 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -4.00 22.00 1.00 15.00 -- 22.46 77.00 -60.00 26 2 \w -9.00 94.00 1.00 15.00 -- 22.46 77.00-180.00 103 3 \w 13.00 78.00 1.00 15.00 -- 22.46 77.00 60.00 65 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0185801000 _diffrn_orient_matrix_UB_12 0.0169949000 _diffrn_orient_matrix_UB_13 0.0227878000 _diffrn_orient_matrix_UB_21 -0.0450829000 _diffrn_orient_matrix_UB_22 -0.0833979000 _diffrn_orient_matrix_UB_23 0.0021499000 _diffrn_orient_matrix_UB_31 0.0930202000 _diffrn_orient_matrix_UB_32 -0.0371568000 _diffrn_orient_matrix_UB_33 0.0056225000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_unetI/netI 0.0742 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 4747 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.020 _diffrn_reflns_theta_max 25.020 _diffrn_reflns_theta_min 2.699 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90701 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.234 _exptl_crystal_description plate _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.205 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.038 _refine_ls_abs_structure_details ; Flack x determined using 404 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.5(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2747 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.1227 _refine_ls_R_factor_gt 0.0804 _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^)+(0.0566P)^2^+0.1203P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1489 _refine_ls_wR_factor_ref 0.1731 _reflns_Friedel_coverage 0.681 _reflns_Friedel_fraction_full 0.997 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 1773 _reflns_number_total 2747 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL shi_4023_cota_a.res in P2(1)2(1)2 shi_4023_cota.res created by SHELXL-2018/3 at 14:07:34 on 04-Dec-2018 REM Old TITL shI_4023_CoTa in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2: R1 0.234, Rweak 0.181, Alpha 0.021 REM 2.031 for 8 systematic absences, Orientation a'=b, b'=c, c'=a REM Flack x = -0.483 ( 2.353 ) from 308 Parsons' quotients REM Formula found by SHELXT: C17 O4 CELL 0.71073 7.6481 30.1858 6.7702 90 90 90 ZERR 4 0.0017 0.0044 0.0006 0 0 0 LATT -1 SYMM -X,-Y,+Z SYMM 0.5-X,0.5+Y,-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O UNIT 68 88 16 EQIV $1 -0.5+X,1.5-Y,2-Z L.S. 10 PLAN 5 SIZE 0.05 0.15 0.2 HTAB O2 O3_$1 conf BOND LIST 4 fmap 2 acta SHEL 99 0.84 OMIT 2 30 2 OMIT 1 29 4 OMIT -8 2 3 OMIT 0 4 1 REM REM REM WGHT 0.056600 0.120300 FVAR 0.41919 O1 3 0.764756 0.480402 0.215335 11.00000 0.14819 0.06076 = 0.07519 -0.01477 -0.00137 0.00445 O2 3 0.474304 0.709275 0.845078 11.00000 0.08542 0.06373 = 0.05478 -0.00653 0.02023 0.02402 AFIX 147 H2 2 0.432419 0.714397 0.954208 11.00000 -1.50000 AFIX 0 O3 3 0.828476 0.753733 0.802060 11.00000 0.09028 0.04282 = 0.04462 -0.00513 -0.02240 -0.00600 O4 3 0.683588 0.806975 0.643221 11.00000 0.11163 0.04690 = 0.08746 -0.00215 -0.01663 0.01026 C1 1 0.777953 0.454416 0.054602 11.00000 0.06756 0.06610 = 0.06178 -0.02821 -0.00494 -0.00488 C2 1 0.798823 0.409933 0.089291 11.00000 0.07606 0.05301 = 0.08503 0.00200 0.00503 -0.00182 AFIX 43 H2A 2 0.801647 0.399653 0.218745 11.00000 -1.20000 AFIX 0 C3 1 0.815321 0.380835 -0.060809 11.00000 0.05875 0.06267 = 0.10946 -0.00334 0.00932 -0.00444 AFIX 43 H3 2 0.827540 0.350742 -0.034802 11.00000 -1.20000 AFIX 0 C4 1 0.813981 0.395811 -0.251160 11.00000 0.07268 0.07129 = 0.08920 -0.02615 0.01370 0.00641 AFIX 43 H4 2 0.827077 0.375894 -0.354912 11.00000 -1.20000 AFIX 0 C5 1 0.793191 0.440551 -0.290341 11.00000 0.07376 0.08304 = 0.06579 -0.00915 0.00427 0.00108 AFIX 43 H5 2 0.790172 0.450344 -0.420539 11.00000 -1.20000 AFIX 0 C6 1 0.776925 0.470727 -0.138556 11.00000 0.08223 0.05731 = 0.06723 -0.02006 -0.00939 0.00273 AFIX 43 H6 2 0.765666 0.500875 -0.163846 11.00000 -1.20000 AFIX 0 C7 1 0.738489 0.526493 0.191765 11.00000 0.08526 0.07140 = 0.06563 -0.02807 0.00774 0.00021 AFIX 23 H7A 2 0.630530 0.532204 0.121016 11.00000 -1.20000 H7B 2 0.834581 0.539612 0.118809 11.00000 -1.20000 AFIX 0 C8 1 0.729452 0.545606 0.400845 11.00000 0.10702 0.06489 = 0.08188 -0.01971 0.00336 -0.00300 AFIX 23 H8A 2 0.635525 0.530967 0.471617 11.00000 -1.20000 H8B 2 0.837831 0.538733 0.468662 11.00000 -1.20000 AFIX 0 C9 1 0.700730 0.593811 0.410080 11.00000 0.08787 0.04956 = 0.08261 -0.01742 0.02676 0.00185 AFIX 23 H9A 2 0.594235 0.601197 0.339580 11.00000 -1.20000 H9B 2 0.797096 0.608898 0.345643 11.00000 -1.20000 AFIX 0 C10 1 0.685949 0.610189 0.627658 11.00000 0.06250 0.04507 = 0.06802 -0.01443 0.01424 -0.01075 AFIX 23 H10A 2 0.601238 0.592000 0.696893 11.00000 -1.20000 H10B 2 0.798098 0.606405 0.692405 11.00000 -1.20000 AFIX 0 C11 1 0.630935 0.658696 0.643039 11.00000 0.04723 0.04774 = 0.04948 -0.00659 0.00670 -0.00394 AFIX 13 H11 2 0.529532 0.664021 0.557791 11.00000 -1.20000 AFIX 0 C12 1 0.585351 0.671161 0.856770 11.00000 0.05945 0.04694 = 0.04477 0.00170 0.01754 0.00486 AFIX 13 H12 2 0.527988 0.646641 0.926060 11.00000 -1.20000 AFIX 0 C13 1 0.762140 0.682128 0.947927 11.00000 0.08402 0.05513 = 0.04645 -0.00408 -0.00310 0.01037 AFIX 23 H13A 2 0.748156 0.700749 1.063623 11.00000 -1.20000 H13B 2 0.823512 0.655318 0.985771 11.00000 -1.20000 AFIX 0 C14 1 0.859721 0.706340 0.787594 11.00000 0.06803 0.03855 = 0.05005 -0.00266 -0.01093 0.00345 AFIX 13 H14 2 0.985076 0.699721 0.792978 11.00000 -1.20000 AFIX 0 C15 1 0.779294 0.691097 0.587850 11.00000 0.05077 0.05109 = 0.03955 -0.01360 0.01220 -0.01181 AFIX 13 H15 2 0.867377 0.676400 0.505644 11.00000 -1.20000 AFIX 0 C16 1 0.719779 0.734736 0.493315 11.00000 0.06648 0.06129 = 0.03969 0.00433 -0.00297 -0.02007 AFIX 23 H16A 2 0.793049 0.741899 0.380813 11.00000 -1.20000 H16B 2 0.599654 0.732353 0.448595 11.00000 -1.20000 AFIX 0 C17 1 0.735311 0.769430 0.646990 11.00000 0.07048 0.04545 = 0.04623 -0.00468 -0.00047 -0.00833 HKLF 4 REM shi_4023_cota_a.res in P2(1)2(1)2 REM wR2 = 0.1731, GooF = S = 1.102, Restrained GooF = 1.102 for all data REM R1 = 0.0804 for 1773 Fo > 4sig(Fo) and 0.1227 for all 2747 data REM 191 parameters refined using 0 restraints END WGHT 0.0566 0.1203 REM Highest difference peak 0.205, deepest hole -0.158, 1-sigma level 0.038 Q1 1 0.6214 0.5707 0.3361 11.00000 0.05 0.20 Q2 1 0.6586 0.5499 0.1170 11.00000 0.05 0.18 Q3 1 0.7950 0.5862 0.7359 11.00000 0.05 0.16 Q4 1 0.6759 0.5037 0.1857 11.00000 0.05 0.16 Q5 1 0.7972 0.5775 0.4730 11.00000 0.05 0.14 REM The information below was added by Olex2. REM REM R1 = 0.0804 for 1773 Fo > 4sig(Fo) and 0.1227 for all 5711 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.20, deepest hole -0.16 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1227 REM R1_gt = 0.0804 REM wR_ref = 0.1731 REM GOOF = 1.102 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 5711 REM Reflections_gt = 1773 REM Parameters = n/a REM Hole = -0.16 REM Peak = 0.20 REM Flack = 0.5(10) ; _cod_data_source_file c9nj01186b2.cif _cod_data_source_block shi_4023_cota _cod_database_code 7058316 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C20H20O4Cl1 _chemical_oxdiff_usercomment TCV-14/092018 _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 0.996 _shelx_estimated_absorpt_t_min 0.983 _reflns_odcompleteness_completeness 99.90 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2.a Ternary CH refined with riding coordinates: C11(H11), C12(H12), C14(H14), C15(H15) 2.b Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C16(H16A,H16B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6) 2.d Idealised tetrahedral OH refined as rotating group: O2(H2) ; _olex2_date_sample_data_collection 2018-11-20 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 1.114 _oxdiff_exptl_absorpt_empirical_full_min 0.875 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -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 O1 O 0.7648(8) 0.48040(14) 0.2153(7) 0.0947(18) Uani 1 1 d . O2 O 0.4743(6) 0.70927(13) 0.8451(6) 0.0680(13) Uani 1 1 d . H2 H 0.432419 0.714397 0.954208 0.102 Uiso 1 1 calc GR O3 O 0.8285(6) 0.75373(11) 0.8021(5) 0.0592(12) Uani 1 1 d . O4 O 0.6836(7) 0.80697(14) 0.6432(7) 0.0820(15) Uani 1 1 d . C1 C 0.7780(9) 0.4544(2) 0.0546(9) 0.0651(18) Uani 1 1 d . C2 C 0.7988(9) 0.4099(2) 0.0893(10) 0.0714(19) Uani 1 1 d . H2A H 0.801647 0.399653 0.218745 0.086 Uiso 1 1 calc R C3 C 0.8153(9) 0.3808(2) -0.0608(12) 0.077(2) Uani 1 1 d . H3 H 0.827540 0.350742 -0.034802 0.092 Uiso 1 1 calc R C4 C 0.8140(10) 0.3958(2) -0.2512(12) 0.078(2) Uani 1 1 d . H4 H 0.827077 0.375894 -0.354912 0.093 Uiso 1 1 calc R C5 C 0.7932(9) 0.4406(2) -0.2903(10) 0.074(2) Uani 1 1 d . H5 H 0.790172 0.450344 -0.420539 0.089 Uiso 1 1 calc R C6 C 0.7769(9) 0.47073(19) -0.1386(9) 0.0689(19) Uani 1 1 d . H6 H 0.765666 0.500875 -0.163846 0.083 Uiso 1 1 calc R C7 C 0.7385(10) 0.52649(19) 0.1918(9) 0.074(2) Uani 1 1 d . H7A H 0.630530 0.532204 0.121016 0.089 Uiso 1 1 calc R H7B H 0.834581 0.539612 0.118809 0.089 Uiso 1 1 calc R C8 C 0.7295(11) 0.5456(2) 0.4008(10) 0.085(2) Uani 1 1 d . H8A H 0.635525 0.530967 0.471617 0.102 Uiso 1 1 calc R H8B H 0.837831 0.538733 0.468662 0.102 Uiso 1 1 calc R C9 C 0.7007(10) 0.59381(19) 0.4101(9) 0.073(2) Uani 1 1 d . H9A H 0.594235 0.601197 0.339580 0.088 Uiso 1 1 calc R H9B H 0.797096 0.608898 0.345643 0.088 Uiso 1 1 calc R C10 C 0.6859(8) 0.61019(17) 0.6277(8) 0.0585(17) Uani 1 1 d . H10A H 0.601238 0.592000 0.696893 0.070 Uiso 1 1 calc R H10B H 0.798098 0.606405 0.692405 0.070 Uiso 1 1 calc R C11 C 0.6309(8) 0.65870(17) 0.6430(8) 0.0481(15) Uani 1 1 d . H11 H 0.529532 0.664021 0.557791 0.058 Uiso 1 1 calc R C12 C 0.5854(8) 0.67116(18) 0.8568(8) 0.0504(15) Uani 1 1 d . H12 H 0.527988 0.646641 0.926060 0.060 Uiso 1 1 calc R C13 C 0.7621(10) 0.68213(18) 0.9479(8) 0.0619(17) Uani 1 1 d . H13A H 0.748156 0.700749 1.063623 0.074 Uiso 1 1 calc R H13B H 0.823512 0.655318 0.985771 0.074 Uiso 1 1 calc R C14 C 0.8597(8) 0.70634(18) 0.7876(8) 0.0522(16) Uani 1 1 d . H14 H 0.985076 0.699721 0.792978 0.063 Uiso 1 1 calc R C15 C 0.7793(8) 0.69110(17) 0.5878(7) 0.0471(14) Uani 1 1 d . H15 H 0.867377 0.676400 0.505644 0.057 Uiso 1 1 calc R C16 C 0.7198(8) 0.73474(17) 0.4933(8) 0.0558(16) Uani 1 1 d . H16A H 0.793049 0.741899 0.380813 0.067 Uiso 1 1 calc R H16B H 0.599654 0.732353 0.448595 0.067 Uiso 1 1 calc R C17 C 0.7353(8) 0.76943(19) 0.6470(8) 0.0541(15) 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 O1 0.148(5) 0.061(3) 0.075(3) -0.015(3) -0.001(4) 0.004(3) O2 0.085(3) 0.064(3) 0.055(2) -0.007(2) 0.020(2) 0.024(2) O3 0.090(3) 0.043(2) 0.045(2) -0.0051(19) -0.022(2) -0.006(2) O4 0.112(4) 0.047(2) 0.087(3) -0.002(3) -0.017(3) 0.010(3) C1 0.068(5) 0.066(4) 0.062(4) -0.028(4) -0.005(4) -0.005(4) C2 0.076(5) 0.053(4) 0.085(5) 0.002(4) 0.005(4) -0.002(4) C3 0.059(5) 0.063(4) 0.109(6) -0.003(5) 0.009(5) -0.004(4) C4 0.073(5) 0.071(5) 0.089(5) -0.026(4) 0.014(5) 0.006(4) C5 0.074(5) 0.083(5) 0.066(4) -0.009(4) 0.004(4) 0.001(4) C6 0.082(5) 0.057(4) 0.067(4) -0.020(4) -0.009(4) 0.003(4) C7 0.085(5) 0.071(4) 0.066(4) -0.028(4) 0.008(4) 0.000(4) C8 0.107(6) 0.065(4) 0.082(5) -0.020(4) 0.003(5) -0.003(4) C9 0.088(5) 0.050(3) 0.083(5) -0.017(3) 0.027(4) 0.002(4) C10 0.063(4) 0.045(3) 0.068(4) -0.014(3) 0.014(4) -0.011(3) C11 0.047(4) 0.048(3) 0.049(3) -0.007(3) 0.007(3) -0.004(3) C12 0.059(4) 0.047(3) 0.045(3) 0.002(3) 0.018(3) 0.005(3) C13 0.084(5) 0.055(4) 0.046(3) -0.004(3) -0.003(4) 0.010(4) C14 0.068(4) 0.039(3) 0.050(3) -0.003(3) -0.011(3) 0.003(3) C15 0.051(4) 0.051(3) 0.040(3) -0.014(3) 0.012(3) -0.012(3) C16 0.066(4) 0.061(4) 0.040(3) 0.004(3) -0.003(3) -0.020(4) C17 0.070(4) 0.045(3) 0.046(3) -0.005(3) 0.000(3) -0.008(3) 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' O O 0.0106 0.0060 '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 C1 O1 C7 119.5(5) C17 O3 C14 112.2(4) O1 C1 C2 116.2(6) O1 C1 C6 123.4(6) C2 C1 C6 120.4(6) C3 C2 C1 121.3(7) C2 C3 C4 119.6(7) C3 C4 C5 120.3(7) C6 C5 C4 120.8(6) C5 C6 C1 117.7(6) O1 C7 C8 105.8(5) C9 C8 C7 114.7(6) C8 C9 C10 111.4(5) C11 C10 C9 112.9(5) C10 C11 C12 111.2(5) C10 C11 C15 112.9(5) C12 C11 C15 103.9(4) O2 C12 C11 106.2(5) O2 C12 C13 112.0(5) C13 C12 C11 103.5(5) C14 C13 C12 104.7(5) O3 C14 C13 110.3(5) O3 C14 C15 106.5(4) C13 C14 C15 106.7(4) C11 C15 C14 105.5(4) C16 C15 C11 115.3(5) C16 C15 C14 103.1(4) C17 C16 C15 106.9(4) O3 C17 C16 109.8(5) O4 C17 O3 121.3(5) O4 C17 C16 128.8(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.345(7) O1 C7 1.415(6) O2 C12 1.432(6) O3 C14 1.454(6) O3 C17 1.354(7) O4 C17 1.201(6) C1 C2 1.372(8) C1 C6 1.397(8) C2 C3 1.349(8) C3 C4 1.366(10) C4 C5 1.385(8) C5 C6 1.379(8) C7 C8 1.530(8) C8 C9 1.473(7) C9 C10 1.558(8) C10 C11 1.527(7) C11 C12 1.535(7) C11 C15 1.544(7) C12 C13 1.523(9) C13 C14 1.506(8) C14 C15 1.555(7) C15 C16 1.534(7) C16 C17 1.481(7) 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 O2 H2 O3 0.82 2.07 2.863(5) 163.0 4_467 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 O1 C1 C2 C3 -179.3(6) O1 C1 C6 C5 179.4(7) O1 C7 C8 C9 -179.5(6) O2 C12 C13 C14 -75.1(5) O3 C14 C15 C11 -116.4(5) O3 C14 C15 C16 4.9(6) C1 O1 C7 C8 179.9(7) C1 C2 C3 C4 1.0(12) C2 C1 C6 C5 1.5(11) C2 C3 C4 C5 -1.0(12) C3 C4 C5 C6 1.2(11) C4 C5 C6 C1 -1.5(10) C6 C1 C2 C3 -1.3(12) C7 O1 C1 C2 -178.4(7) C7 O1 C1 C6 3.7(10) C7 C8 C9 C10 177.8(6) C8 C9 C10 C11 -172.0(6) C9 C10 C11 C12 169.6(5) C9 C10 C11 C15 -74.1(7) C10 C11 C12 O2 -157.8(5) C10 C11 C12 C13 84.1(6) C10 C11 C15 C14 -98.4(5) C10 C11 C15 C16 148.6(5) C11 C12 C13 C14 38.9(6) C11 C15 C16 C17 104.2(5) C12 C11 C15 C14 22.1(6) C12 C11 C15 C16 -90.9(5) C12 C13 C14 O3 90.5(5) C12 C13 C14 C15 -24.9(6) C13 C14 C15 C11 1.5(6) C13 C14 C15 C16 122.8(5) C14 O3 C17 O4 173.1(6) C14 O3 C17 C16 -9.6(7) C14 C15 C16 C17 -10.2(6) C15 C11 C12 O2 80.5(5) C15 C11 C12 C13 -37.6(6) C15 C16 C17 O3 12.5(7) C15 C16 C17 O4 -170.4(7) C17 O3 C14 C13 -112.8(5) C17 O3 C14 C15 2.6(6)