#------------------------------------------------------------------------------ #$Date: 2020-03-05 01:31:34 +0200 (Thu, 05 Mar 2020) $ #$Revision: 248802 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125699.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_7125699 loop_ _publ_author_name 'Ruan, Qing-Feng' 'Jiang, Shi-Qin' 'Zheng, Xiao-Yun' 'Tang, Yu-Qian' 'Yang, Bao' 'Yi, Tao' 'Jin, Jing' 'Cui, Hui' 'Zhao, Zhongxiang' _publ_section_title ; Pseudoguaianelactones A-C: three unusual sesquiterpenoids from Lindera glauca with anti-inflammatory activities by inhibiting the LPS-induced expression of iNOS and COX-2. ; _journal_issue 10 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1517 _journal_page_last 1520 _journal_paper_doi 10.1039/c9cc09159a _journal_volume 56 _journal_year 2020 _chemical_absolute_configuration ad _chemical_compound_source 'Lindera glauca, Lindera, Lauraceae' _chemical_formula_moiety 'C15 H22 O3' _chemical_formula_sum 'C15 H22 O3' _chemical_formula_weight 250.32 _chemical_melting_point 418.6(5) _chemical_name_common 'Guaianelactone C' _chemical_name_systematic (4R,7S,7aS,10R,10aR)-10-hydroxy-7,10-dimethyl-3-methyleneoctahydro-4,10a-methanocyclopenta[b]oxonin-2(3H)-one _chemical_properties_physical Efflorescent _space_group_crystal_system tetragonal _space_group_IT_number 92 _space_group_name_Hall 'P 4abw 2nw' _space_group_name_H-M_alt 'P 41 21 2' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-11-23 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-08-04 deposited with the CCDC. 2019-12-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.72709(4) _cell_length_b 9.72709(4) _cell_length_c 28.60837(18) _cell_measurement_reflns_used 25792 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 76.8010 _cell_measurement_theta_min 4.7790 _cell_volume 2706.82(2) _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_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _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 -26.00 -1.00 0.50 0.05 -- -46.62 94.00-117.00 50 2 \w 11.00 36.00 0.50 0.05 -- 46.62 -38.00-114.00 50 3 \w 52.00 77.00 0.50 0.05 -- 46.62 38.00 40.00 50 4 \w 7.00 32.00 0.50 0.05 -- 46.62-100.00 37.00 50 5 \w -25.00 44.00 0.50 0.05 -- 46.62 -94.00 131.00 138 6 \w -92.00 -67.00 0.50 0.10 -- -100.00 94.00-117.00 50 7 \w -151.00-126.00 0.50 0.10 -- -100.00 -94.00 131.00 50 8 \w -154.00-129.00 0.50 0.10 -- -100.00 -38.00-114.00 50 9 \w 111.00 137.00 0.50 0.10 -- 107.00 38.00 40.00 52 10 \w 35.00 86.00 0.50 0.10 -- 107.00 -94.00 131.00 102 11 \w 77.00 108.00 0.50 0.10 -- 107.00 -38.00-114.00 62 12 \w 104.00 134.00 0.50 0.10 -- 107.00 100.00 142.00 60 13 \w 126.00 152.00 0.50 0.10 -- 107.00 94.00-117.00 52 14 \w 35.00 64.00 0.50 0.05 -- 46.62 57.00 150.00 58 15 \w 32.00 119.00 0.50 0.05 -- 46.62 38.00 120.00 174 16 \w 75.00 120.00 0.50 0.05 -- 46.62 77.00-180.00 90 17 \w 26.00 69.00 0.50 0.05 -- 46.62 77.00-180.00 86 18 \w -104.00 -78.00 0.50 0.10 -- -100.00 -73.00 153.98 52 19 \w -111.00 -75.00 0.50 0.10 -- -100.00 -79.00 170.04 72 20 \w -104.00 -78.00 0.50 0.10 -- -100.00 -72.00 178.37 52 21 \w -154.00-128.00 0.50 0.10 -- -100.00 -77.00 150.00 52 22 \w -102.00 -76.00 0.50 0.10 -- -100.00 -77.00-180.00 52 23 \w -105.00 -79.00 0.50 0.10 -- -100.00 -77.00 150.00 52 24 \w -172.00 -81.00 0.50 0.10 -- -100.00 -65.00 122.13 182 25 \w -157.00-127.00 0.50 0.10 -- -100.00 -55.00 151.17 60 26 \w -164.00 -81.00 0.50 0.10 -- -100.00 -66.00 148.59 166 27 \w -103.00 -77.00 0.50 0.10 -- -100.00 -78.00 154.44 52 28 \w -167.00 -85.00 0.50 0.10 -- -100.00 -45.00 0.00 164 29 \w -154.00-122.00 0.50 0.10 -- -100.00 -77.00-180.00 64 30 \w -102.00 -76.00 0.50 0.10 -- -100.00 -77.00 120.00 52 31 \w -123.00 -87.00 0.50 0.10 -- -100.00 -55.00 151.17 72 32 \w -115.00 -80.00 0.50 0.10 -- -100.00 -70.00 135.90 70 33 \w 36.00 121.00 0.50 0.10 -- 107.00 -45.00 30.00 170 34 \w 93.00 176.00 0.50 0.10 -- 107.00 45.00 -90.00 166 35 \w 34.00 109.00 0.50 0.10 -- 107.00 -94.00 -30.00 150 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1460968000 _diffrn_orient_matrix_UB_12 0.0004073000 _diffrn_orient_matrix_UB_13 -0.0208342000 _diffrn_orient_matrix_UB_21 0.0185865000 _diffrn_orient_matrix_UB_22 0.1505538000 _diffrn_orient_matrix_UB_23 0.0154601000 _diffrn_orient_matrix_UB_31 0.0583392000 _diffrn_orient_matrix_UB_32 -0.0491144000 _diffrn_orient_matrix_UB_33 0.0471830000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_unetI/netI 0.0154 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 28910 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.071 _diffrn_reflns_theta_min 4.802 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.229 _exptl_crystal_description tetragonal _exptl_crystal_F_000 1088 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethyl acetate/methanol/water (9:1:0.5)' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.179 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.030 _refine_ls_abs_structure_details ; Flack x determined using 1018 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2656 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0261 _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^)+(0.0382P)^2^+0.4839P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.0690 _reflns_Friedel_coverage 0.636 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 2616 _reflns_number_total 2656 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09159a2.cif _cod_data_source_block zzx_shj_181113 _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '418.15-419.15' was changed to '418.6(5)' -- the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7125698--7125699.cif. ; _cod_original_cell_volume 2706.82(3) _cod_database_code 7125699 _shelx_shelxl_version_number 2016/6 _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 0.936 _shelx_estimated_absorpt_t_min 0.824 _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _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 C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C007(H007), C008(H008), C00A(H00D) 2.b Secondary CH2 refined with riding coordinates: C00D(H00H,H00I), C00E(H00J,H00K), C00G(H00N,H00O), C00H(H00P,H00Q), C00I(H00R, H00S) 2.c Idealised Me refined as rotating group: C006(H00A,H00B,H00C), C00B(H00E,H00F,H00G) 2.d Idealised tetrahedral OH refined as rotating group: O003(H003) ; _shelx_res_file ; TITL zzx_shj_181113_a.res in P4(1)2(1)2 zzx_shj_181113.res created by SHELXL-2016/6 at 16:15:57 on 23-Nov-2018 REM Old TITL zzx_SHJ_181113 in P4(1)2(1)2 REM SHELXT solution in P4(1)2(1)2: R1 0.091, Rweak 0.022, Alpha 0.001 REM 0.970 for 32 systematic absences, Orientation as input REM Flack x = 0.054 ( 0.075 ) from 1051 Parsons' quotients REM Formula found by SHELXT: C15 O3 CELL 1.54184 9.727088 9.727088 28.608369 90 90 90 ZERR 8 0.00004 0.00004 0.000182 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-Y,0.5+X,0.25+Z SYMM 0.5+Y,0.5-X,0.75+Z SYMM 0.5-X,0.5+Y,0.25-Z SYMM 0.5+X,0.5-Y,0.75-Z SYMM +Y,+X,-Z SYMM -Y,-X,0.5-Z SFAC C H O UNIT 120 176 24 L.S. 10 PLAN 20 SIZE 0.3 0.2 0.1 BOND $h htab conf list 4 fmap 2 acta SHEL 999 0.81 REM REM REM WGHT 0.038200 0.483900 FVAR 0.66111 O001 3 0.550562 0.933188 0.394268 11.00000 0.01502 0.01622 = 0.01599 0.00075 0.00082 -0.00002 O002 3 0.677260 1.057298 0.347588 11.00000 0.02078 0.01967 = 0.02207 0.00140 0.00300 -0.00135 O003 3 0.270575 0.712819 0.427722 11.00000 0.01998 0.02316 = 0.02698 -0.00342 0.00433 -0.00629 AFIX 147 H003 2 0.249133 0.634346 0.420203 11.00000 -1.50000 AFIX 0 C004 1 0.568612 1.046436 0.368595 11.00000 0.02036 0.01609 = 0.01355 -0.00176 -0.00292 -0.00217 C005 1 0.407024 0.741398 0.411797 11.00000 0.01656 0.01906 = 0.01986 -0.00061 0.00223 -0.00252 C006 1 0.426431 0.694136 0.361513 11.00000 0.02356 0.02095 = 0.02218 -0.00337 0.00099 -0.00115 AFIX 137 H00A 2 0.412071 0.596650 0.359631 11.00000 -1.50000 H00B 2 0.518081 0.715626 0.351433 11.00000 -1.50000 H00C 2 0.361381 0.740323 0.341758 11.00000 -1.50000 AFIX 0 C007 1 0.547707 1.029031 0.489469 11.00000 0.02560 0.02265 = 0.01358 -0.00234 -0.00065 -0.00018 AFIX 13 H007 2 0.531349 1.038070 0.523130 11.00000 -1.20000 AFIX 0 C008 1 0.450041 0.913220 0.473051 11.00000 0.02035 0.02194 = 0.01499 -0.00056 0.00172 -0.00008 AFIX 13 H008 2 0.360500 0.933132 0.487218 11.00000 -1.20000 AFIX 0 C009 1 0.423435 0.898485 0.419680 11.00000 0.01548 0.01907 = 0.01583 -0.00108 0.00263 -0.00162 C00A 1 0.339716 1.136065 0.400476 11.00000 0.01923 0.02186 = 0.02074 -0.00255 -0.00169 0.00611 AFIX 13 H00D 2 0.260557 1.185310 0.387488 11.00000 -1.20000 AFIX 0 C00B 1 0.702068 1.000773 0.484622 11.00000 0.02443 0.02622 = 0.02075 -0.00059 -0.00431 -0.00249 AFIX 137 H00E 2 0.724775 0.917353 0.500807 11.00000 -1.50000 H00F 2 0.752984 1.075797 0.497876 11.00000 -1.50000 H00G 2 0.725128 0.991471 0.452148 11.00000 -1.50000 AFIX 0 C00C 1 0.457546 1.152179 0.366852 11.00000 0.02150 0.01815 = 0.01858 -0.00311 -0.00488 0.00014 C00D 1 0.511193 0.681341 0.446080 11.00000 0.02478 0.01880 = 0.02357 0.00231 -0.00136 -0.00087 AFIX 23 H00H 2 0.604157 0.690550 0.434218 11.00000 -1.20000 H00I 2 0.492499 0.584979 0.452060 11.00000 -1.20000 AFIX 0 C00E 1 0.303774 0.983263 0.401800 11.00000 0.01639 0.02375 = 0.01923 -0.00211 0.00057 0.00010 AFIX 23 H00J 2 0.224778 0.969340 0.421944 11.00000 -1.20000 H00K 2 0.279302 0.952668 0.370620 11.00000 -1.20000 AFIX 0 C00F 1 0.468153 1.251828 0.335170 11.00000 0.02720 0.02191 = 0.02765 0.00214 -0.00602 0.00160 C00G 1 0.490960 0.767454 0.490346 11.00000 0.03066 0.02384 = 0.01885 0.00379 -0.00247 -0.00340 AFIX 23 H00N 2 0.575284 0.771175 0.508402 11.00000 -1.20000 H00O 2 0.418898 0.728617 0.509709 11.00000 -1.20000 AFIX 0 C00H 1 0.372188 1.199345 0.448918 11.00000 0.03051 0.02199 = 0.02329 -0.00544 -0.00078 0.00663 AFIX 23 H00P 2 0.359318 1.298036 0.446800 11.00000 -1.20000 H00Q 2 0.305228 1.164751 0.471120 11.00000 -1.20000 AFIX 0 C00I 1 0.515652 1.172330 0.468689 11.00000 0.03129 0.01962 = 0.01982 -0.00576 -0.00336 -0.00032 AFIX 23 H00R 2 0.532597 1.240019 0.492912 11.00000 -1.20000 H00S 2 0.581502 1.189484 0.443903 11.00000 -1.20000 AFIX 0 H00L 2 0.396962 1.320972 0.332929 11.00000 0.03150 H00M 2 0.547657 1.254510 0.314128 11.00000 0.02970 HKLF 4 REM zzx_shj_181113_a.res in P4(1)2(1)2 REM R1 = 0.0261 for 2616 Fo > 4sig(Fo) and 0.0266 for all 2656 data REM 174 parameters refined using 0 restraints END WGHT 0.0381 0.4842 REM Instructions for potential hydrogen bonds EQIV $1 x-1/2, -y+3/2, -z+3/4 HTAB O003 O002_$1 REM Highest difference peak 0.179, deepest hole -0.155, 1-sigma level 0.030 Q1 1 0.5029 0.9676 0.4799 11.00000 0.05 0.18 Q2 1 0.5024 1.0970 0.3661 11.00000 0.05 0.17 Q3 1 0.4164 0.8213 0.4144 11.00000 0.05 0.16 Q4 1 0.3600 0.9479 0.4125 11.00000 0.05 0.15 Q5 1 0.4517 0.8446 0.4842 11.00000 0.05 0.14 Q6 1 0.5223 1.0998 0.4768 11.00000 0.05 0.12 Q7 1 0.4085 1.1405 0.3842 11.00000 0.05 0.12 Q8 1 0.4372 0.9083 0.4479 11.00000 0.05 0.12 Q9 1 0.6191 1.0028 0.4848 11.00000 0.05 0.12 Q10 1 0.4869 1.2242 0.3631 11.00000 0.05 0.12 Q11 1 0.3325 1.0638 0.4013 11.00000 0.05 0.12 Q12 1 0.3613 1.1595 0.4235 11.00000 0.05 0.12 Q13 1 0.4355 1.1720 0.3419 11.00000 0.05 0.11 Q14 1 0.6163 0.8551 0.3912 11.00000 0.05 0.10 Q15 1 0.7337 0.9940 0.3488 11.00000 0.05 0.10 Q16 1 0.4212 0.7193 0.3875 11.00000 0.05 0.10 Q17 1 0.4587 0.7100 0.4259 11.00000 0.05 0.09 Q18 1 0.7452 1.1493 0.3503 11.00000 0.05 0.09 Q19 1 0.7029 0.8021 0.4171 11.00000 0.05 0.09 Q20 1 0.6711 1.1668 0.3335 11.00000 0.05 0.08 ; _shelx_res_checksum 38033 _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 1.473 _oxdiff_exptl_absorpt_empirical_full_min 0.723 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -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 O001 O 0.55056(9) 0.93319(9) 0.39427(3) 0.0157(2) Uani 1 1 d . O002 O 0.67726(10) 1.05730(10) 0.34759(3) 0.0208(2) Uani 1 1 d . O003 O 0.27057(11) 0.71282(11) 0.42772(4) 0.0234(2) Uani 1 1 d . H003 H 0.249133 0.634346 0.420203 0.035 Uiso 1 1 calc GR C004 C 0.56861(14) 1.04644(14) 0.36860(4) 0.0167(3) Uani 1 1 d . C005 C 0.40702(15) 0.74140(15) 0.41180(5) 0.0185(3) Uani 1 1 d . C006 C 0.42643(16) 0.69414(15) 0.36151(5) 0.0222(3) Uani 1 1 d . H00A H 0.412071 0.596650 0.359631 0.033 Uiso 1 1 calc GR H00B H 0.518081 0.715626 0.351433 0.033 Uiso 1 1 calc GR H00C H 0.361381 0.740323 0.341758 0.033 Uiso 1 1 calc GR C007 C 0.54771(15) 1.02903(15) 0.48947(5) 0.0206(3) Uani 1 1 d . H007 H 0.531349 1.038070 0.523130 0.025 Uiso 1 1 calc R C008 C 0.45004(15) 0.91322(15) 0.47305(5) 0.0191(3) Uani 1 1 d . H008 H 0.360500 0.933132 0.487218 0.023 Uiso 1 1 calc R C009 C 0.42343(14) 0.89849(14) 0.41968(5) 0.0168(3) Uani 1 1 d . C00A C 0.33972(15) 1.13606(15) 0.40048(5) 0.0206(3) Uani 1 1 d . H00D H 0.260557 1.185310 0.387488 0.025 Uiso 1 1 calc R C00B C 0.70207(16) 1.00077(16) 0.48462(5) 0.0238(3) Uani 1 1 d . H00E H 0.724775 0.917353 0.500807 0.036 Uiso 1 1 calc GR H00F H 0.752984 1.075797 0.497876 0.036 Uiso 1 1 calc GR H00G H 0.725128 0.991471 0.452148 0.036 Uiso 1 1 calc GR C00C C 0.45755(15) 1.15218(15) 0.36685(5) 0.0194(3) Uani 1 1 d . C00D C 0.51119(16) 0.68134(15) 0.44608(5) 0.0224(3) Uani 1 1 d . H00H H 0.604157 0.690550 0.434218 0.027 Uiso 1 1 calc R H00I H 0.492499 0.584979 0.452060 0.027 Uiso 1 1 calc R C00E C 0.30377(15) 0.98326(15) 0.40180(5) 0.0198(3) Uani 1 1 d . H00J H 0.224778 0.969340 0.421944 0.024 Uiso 1 1 calc R H00K H 0.279302 0.952668 0.370620 0.024 Uiso 1 1 calc R C00F C 0.46815(18) 1.25183(16) 0.33517(6) 0.0256(3) Uani 1 1 d . C00G C 0.49096(17) 0.76745(16) 0.49035(5) 0.0244(3) Uani 1 1 d . H00N H 0.575284 0.771175 0.508402 0.029 Uiso 1 1 calc R H00O H 0.418898 0.728617 0.509709 0.029 Uiso 1 1 calc R C00H C 0.37219(17) 1.19934(16) 0.44892(5) 0.0253(3) Uani 1 1 d . H00P H 0.359318 1.298036 0.446800 0.030 Uiso 1 1 calc R H00Q H 0.305228 1.164751 0.471120 0.030 Uiso 1 1 calc R C00I C 0.51565(17) 1.17233(15) 0.46869(5) 0.0236(3) Uani 1 1 d . H00R H 0.532597 1.240019 0.492912 0.028 Uiso 1 1 calc R H00S H 0.581502 1.189484 0.443903 0.028 Uiso 1 1 calc R H00L H 0.397(2) 1.321(2) 0.3329(7) 0.031(5) Uiso 1 1 d . H00M H 0.548(2) 1.255(2) 0.3141(7) 0.030(5) 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 O001 0.0150(4) 0.0162(5) 0.0160(4) 0.0007(4) 0.0008(3) 0.0000(4) O002 0.0208(5) 0.0197(5) 0.0221(5) 0.0014(4) 0.0030(4) -0.0014(4) O003 0.0200(5) 0.0232(5) 0.0270(5) -0.0034(4) 0.0043(4) -0.0063(4) C004 0.0204(7) 0.0161(6) 0.0135(6) -0.0018(5) -0.0029(5) -0.0022(5) C005 0.0166(7) 0.0191(7) 0.0199(6) -0.0006(5) 0.0022(5) -0.0025(5) C006 0.0236(7) 0.0209(7) 0.0222(7) -0.0034(6) 0.0010(6) -0.0012(6) C007 0.0256(8) 0.0227(7) 0.0136(6) -0.0023(5) -0.0007(5) -0.0002(6) C008 0.0203(7) 0.0219(7) 0.0150(6) -0.0006(5) 0.0017(5) -0.0001(6) C009 0.0155(6) 0.0191(7) 0.0158(6) -0.0011(5) 0.0026(5) -0.0016(5) C00A 0.0192(7) 0.0219(7) 0.0207(7) -0.0025(6) -0.0017(6) 0.0061(6) C00B 0.0244(8) 0.0262(8) 0.0207(6) -0.0006(6) -0.0043(6) -0.0025(6) C00C 0.0215(7) 0.0182(7) 0.0186(6) -0.0031(5) -0.0049(5) 0.0001(6) C00D 0.0248(8) 0.0188(7) 0.0236(7) 0.0023(6) -0.0014(6) -0.0009(6) C00E 0.0164(7) 0.0237(7) 0.0192(6) -0.0021(5) 0.0006(5) 0.0001(6) C00F 0.0272(8) 0.0219(7) 0.0276(7) 0.0021(6) -0.0060(6) 0.0016(6) C00G 0.0307(8) 0.0238(8) 0.0189(6) 0.0038(6) -0.0025(6) -0.0034(6) C00H 0.0305(8) 0.0220(8) 0.0233(7) -0.0054(6) -0.0008(6) 0.0066(6) C00I 0.0313(8) 0.0196(7) 0.0198(6) -0.0058(6) -0.0034(6) -0.0003(6) 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' O O 0.0492 0.0322 '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 C004 O001 C009 124.79(11) C005 O003 H003 109.5 O001 C004 C00C 119.45(12) O002 C004 O001 117.13(12) O002 C004 C00C 123.42(13) O003 C005 C006 110.94(12) O003 C005 C009 103.91(11) O003 C005 C00D 109.69(12) C006 C005 C009 114.95(12) C006 C005 C00D 114.17(13) C00D C005 C009 102.42(11) C005 C006 H00A 109.5 C005 C006 H00B 109.5 C005 C006 H00C 109.5 H00A C006 H00B 109.5 H00A C006 H00C 109.5 H00B C006 H00C 109.5 C008 C007 H007 105.3 C008 C007 C00I 114.57(12) C00B C007 H007 105.3 C00B C007 C008 116.34(12) C00B C007 C00I 108.92(12) C00I C007 H007 105.3 C007 C008 H008 106.0 C007 C008 C009 117.87(11) C007 C008 C00G 114.25(12) C009 C008 H008 106.0 C00G C008 H008 106.0 C00G C008 C009 105.74(11) O001 C009 C005 103.89(10) O001 C009 C008 108.88(11) O001 C009 C00E 110.69(11) C005 C009 C008 104.50(11) C00E C009 C005 114.05(12) C00E C009 C008 114.14(11) C00C C00A H00D 107.8 C00C C00A C00E 106.95(11) C00C C00A C00H 112.04(12) C00E C00A H00D 107.8 C00E C00A C00H 114.28(12) C00H C00A H00D 107.8 C007 C00B H00E 109.5 C007 C00B H00F 109.5 C007 C00B H00G 109.5 H00E C00B H00F 109.5 H00E C00B H00G 109.5 H00F C00B H00G 109.5 C004 C00C C00A 117.28(12) C00F C00C C004 117.94(14) C00F C00C C00A 124.77(14) C005 C00D H00H 111.0 C005 C00D H00I 111.0 C005 C00D C00G 103.70(12) H00H C00D H00I 109.0 C00G C00D H00H 111.0 C00G C00D H00I 111.0 C009 C00E C00A 111.23(12) C009 C00E H00J 109.4 C009 C00E H00K 109.4 C00A C00E H00J 109.4 C00A C00E H00K 109.4 H00J C00E H00K 108.0 C00C C00F H00L 119.7(12) C00C C00F H00M 119.9(12) H00L C00F H00M 120.4(17) C008 C00G H00N 110.6 C008 C00G H00O 110.6 C00D C00G C008 105.59(11) C00D C00G H00N 110.6 C00D C00G H00O 110.6 H00N C00G H00O 108.8 C00A C00H H00P 108.1 C00A C00H H00Q 108.1 H00P C00H H00Q 107.3 C00I C00H C00A 116.68(12) C00I C00H H00P 108.1 C00I C00H H00Q 108.1 C007 C00I H00R 107.6 C007 C00I H00S 107.6 C00H C00I C007 118.76(13) C00H C00I H00R 107.6 C00H C00I H00S 107.6 H00R C00I H00S 107.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O001 C004 1.3356(16) O001 C009 1.4736(16) O002 C004 1.2203(17) O003 H003 0.8200 O003 C005 1.4305(17) C004 C00C 1.4925(19) C005 C006 1.5220(19) C005 C009 1.5528(19) C005 C00D 1.526(2) C006 H00A 0.9600 C006 H00B 0.9600 C006 H00C 0.9600 C007 H007 0.9800 C007 C008 1.547(2) C007 C00B 1.533(2) C007 C00I 1.547(2) C008 H008 0.9800 C008 C009 1.5552(18) C008 C00G 1.554(2) C009 C00E 1.5154(19) C00A H00D 0.9800 C00A C00C 1.505(2) C00A C00E 1.527(2) C00A C00H 1.549(2) C00B H00E 0.9600 C00B H00F 0.9600 C00B H00G 0.9600 C00C C00F 1.331(2) C00D H00H 0.9700 C00D H00I 0.9700 C00D C00G 1.531(2) C00E H00J 0.9700 C00E H00K 0.9700 C00F H00L 0.97(2) C00F H00M 0.98(2) C00G H00N 0.9700 C00G H00O 0.9700 C00H H00P 0.9700 C00H H00Q 0.9700 C00H C00I 1.529(2) C00I H00R 0.9700 C00I H00S 0.9700 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 O001 C004 C00C C00A 9.67(19) O001 C004 C00C C00F -168.91(13) O001 C009 C00E C00A -50.46(14) O002 C004 C00C C00A -170.29(12) O002 C004 C00C C00F 11.1(2) O003 C005 C009 O001 -168.23(10) O003 C005 C009 C008 77.68(13) O003 C005 C009 C00E -47.63(14) O003 C005 C00D C00G -67.09(14) C004 O001 C009 C005 139.73(11) C004 O001 C009 C008 -109.34(13) C004 O001 C009 C00E 16.91(16) C005 C009 C00E C00A -167.17(11) C005 C00D C00G C008 -32.68(15) C006 C005 C009 O001 -46.81(15) C006 C005 C009 C008 -160.91(12) C006 C005 C009 C00E 73.78(16) C006 C005 C00D C00G 167.70(12) C007 C008 C009 O001 35.18(16) C007 C008 C009 C005 145.69(12) C007 C008 C009 C00E -89.06(15) C007 C008 C00G C00D -121.61(13) C008 C007 C00I C00H 20.27(18) C008 C009 C00E C00A 72.80(15) C009 O001 C004 O002 -176.20(11) C009 O001 C004 C00C 3.84(18) C009 C005 C00D C00G 42.80(14) C009 C008 C00G C00D 9.66(15) C00A C00H C00I C007 -76.03(18) C00B C007 C008 C009 -79.11(16) C00B C007 C008 C00G 45.97(16) C00B C007 C00I C00H 152.52(13) C00C C00A C00E C009 62.03(14) C00C C00A C00H C00I -42.62(19) C00D C005 C009 O001 77.57(12) C00D C005 C009 C008 -36.52(14) C00D C005 C009 C00E -161.83(11) C00E C00A C00C C004 -41.23(16) C00E C00A C00C C00F 137.25(15) C00E C00A C00H C00I 79.24(17) C00G C008 C009 O001 -93.99(13) C00G C008 C009 C005 16.52(14) C00G C008 C009 C00E 141.77(12) C00H C00A C00C C004 84.73(15) C00H C00A C00C C00F -96.79(17) C00H C00A C00E C009 -62.58(15) C00I C007 C008 C009 49.51(18) C00I C007 C008 C00G 174.58(12)