#------------------------------------------------------------------------------ #$Date: 2014-07-05 13:55:20 +0300 (Sat, 05 Jul 2014) $ #$Revision: 119168 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/65/1516596.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_1516596 loop_ _publ_author_name 'Chen, Jian-Jun' 'Chen, Chao-Jun' 'Yao, Xiao-Jun' 'Jin, Xiao-Jie' 'Gao, Kun' _publ_section_title ; Eremophilane-Type Sesquiterpenoids with Diverse Skeletons from Ligularia sagitta. ; _journal_issue 6 _journal_name_full 'Journal of natural products' _journal_page_first 1329 _journal_page_last 1335 _journal_paper_doi 10.1021/np5003302 _journal_volume 77 _journal_year 2014 _chemical_absolute_configuration ad _chemical_formula_moiety 'C19 H26 O6' _chemical_formula_sum 'C19 H26 O6' _chemical_formula_weight 350.40 _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2013-01-28 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.1403(2) _cell_length_b 12.3986(3) _cell_length_c 15.0582(4) _cell_measurement_reflns_used 7077 _cell_measurement_temperature 292.11(10) _cell_measurement_theta_max 72.6290 _cell_measurement_theta_min 4.8060 _cell_volume 1706.50(7) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _diffrn_ambient_temperature 292.11(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9679 _diffrn_measured_fraction_theta_max 0.9906 _diffrn_measurement_details ; 1 omega -9.00 67.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -150.0000 76 2 omega -20.00 15.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -180.0000 35 3 omega -70.00 13.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -58.0000 57.0000 -90.0000 83 4 omega -96.00 -11.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -58.0000 125.0000 -60.0000 85 5 omega 87.00 129.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 58.0000 77.0000 -180.0000 42 6 omega 26.00 51.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 58.0000 77.0000 -180.0000 25 7 omega -138.00 -71.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 -38.0000 120.0000 67 8 omega 41.00 78.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -25.0000 -120.0000 37 9 omega 64.00 90.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -25.0000 -180.0000 26 10 omega 46.00 74.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -25.0000 -90.0000 28 11 omega 53.00 78.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -91.0000 150.0000 25 12 omega 42.00 73.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -111.0000 0.0000 31 13 omega 89.00 116.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -111.0000 0.0000 27 14 omega 50.00 86.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -77.0000 -30.0000 36 15 omega 123.00 174.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 50.0000 -30.0000 51 16 omega 45.00 97.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -77.0000 0.0000 52 17 omega 84.00 113.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -111.0000 -120.0000 29 18 omega 83.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 77.0000 -150.0000 94 19 omega 79.00 107.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -111.0000 150.0000 28 20 omega 111.00 137.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -77.0000 0.0000 26 21 omega 140.00 166.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 50.0000 60.0000 26 22 omega 91.00 116.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -111.0000 60.0000 25 23 omega 44.00 74.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -111.0000 150.0000 30 24 omega 130.00 155.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -91.0000 150.0000 25 25 omega 102.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 178.0000 120.0000 26 26 omega 57.00 82.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -24.0000 61.2978 25 27 omega 102.00 136.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 111.0000 -180.0000 34 28 omega 66.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -38.0000 -150.0000 25 29 omega 135.00 174.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 111.0000 0.0000 39 30 omega 50.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -38.0000 150.0000 26 31 omega 42.00 68.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -10.0000 -123.0000 26 32 omega 111.00 137.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 -10.0000 -123.0000 26 33 omega 125.00 150.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 116.0000 178.0000 90.0000 25 34 omega -82.00 -34.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 30.0000 48 35 omega -71.00 24.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -57.0000 60.0000 95 36 omega -91.00 14.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -58.0000 77.0000 150.0000 105 37 omega -129.00 -34.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -58.0000 -57.0000 30.0000 95 38 omega -130.00 -55.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -58.0000 -77.0000 -30.0000 75 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0199789000 _diffrn_orient_matrix_UB_12 0.1032558000 _diffrn_orient_matrix_UB_13 0.0557386000 _diffrn_orient_matrix_UB_21 -0.0149689000 _diffrn_orient_matrix_UB_22 0.0690551000 _diffrn_orient_matrix_UB_23 -0.0846966000 _diffrn_orient_matrix_UB_31 -0.1664884000 _diffrn_orient_matrix_UB_32 0.0061582000 _diffrn_orient_matrix_UB_33 0.0141659000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_unetI/netI 0.0137 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 10415 _diffrn_reflns_theta_full 72.00 _diffrn_reflns_theta_max 72.54 _diffrn_reflns_theta_min 5.66 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) 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 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.276 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 3358 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0344 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.0962 _reflns_number_gt 3288 _reflns_number_total 3358 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file np5003302_si_002.cif _[local]_cod_data_source_block chengjj0125 _cod_depositor_comments 'Adding full bibliography for 1516596.cif.' _cod_database_code 1516596 _reflns_odcompleteness_completeness 96.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H1A of C1, {H2A,H2B} of C2, {H3A,H3B} of C3, H4 of C4, H6 of C6, {H9A,H9B} of C9, H12 of C12, {H16A,H16B} of C16, {H19B,H19A,H19D,H19C} of C19 At 1.5 times of: H6B of O6B, H1 of O1, H2 of O2, H6A of O6A, {H13A,H13B,H13C} of C13, {H14A, H14B,H14C} of C14, {H15A,H15B,H15C} of C15 2. Others Fixed Sof: O6A(0.56) H6A(0.56) O6B(0.44) H6B(0.44) H19B(0.56) H19A(0.56) H19D(0.44) H19C(0.44) 3.a Ternary CH refined with riding coordinates: C1(H1A), C4(H4), C6(H6), C12(H12) 3.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C16(H16A,H16B), C19(H19B,H19A), C19(H19D,H19C) 3.c Tetrahedral OH refined with riding coordinates: O6A(H6A), O6B(H6B) 3.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) 3.e Idealised tetrahedral OH refined as rotating group: O1(H1), O2(H2) ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7935(2) 0.10358(11) 0.77455(10) 0.0662(4) Uani 1 1 d . . . H1 H 0.8537 0.0682 0.8025 0.099 Uiso 1 1 calc R . . O2 O 0.36003(10) 0.35086(9) 0.63157(7) 0.0365(2) Uani 1 1 d . . . H2 H 0.3548 0.2994 0.5975 0.055 Uiso 1 1 calc R . . O3 O 0.78021(12) 0.32111(9) 0.47509(6) 0.0385(2) Uani 1 1 d . . . O4 O 0.78225(11) 0.39239(9) 0.73981(6) 0.0350(2) Uani 1 1 d . . . O5 O 0.84526(16) 0.55855(10) 0.70805(9) 0.0537(3) Uani 1 1 d . . . O6A O 1.1171(2) 0.46978(18) 0.59071(17) 0.0504(5) Uani 0.56 1 d P A 1 H6A H 1.1786 0.4605 0.5518 0.076 Uiso 0.56 1 calc PR A 1 O6B O 1.0750(2) 0.3727(3) 0.67227(18) 0.0575(8) Uani 0.44 1 d P A 2 H6B H 1.0136 0.3379 0.6997 0.086 Uiso 0.44 1 calc PR A 2 C1 C 0.8116(2) 0.21549(15) 0.79462(11) 0.0474(4) Uani 1 1 d . . . H1A H 0.9163 0.2325 0.7932 0.057 Uiso 1 1 calc R . . C2 C 0.7530(2) 0.24312(18) 0.88603(11) 0.0546(5) Uani 1 1 d . . . H2A H 0.7878 0.3142 0.9028 0.065 Uiso 1 1 calc R . . H2B H 0.7912 0.1917 0.9287 0.065 Uiso 1 1 calc R . . C3 C 0.5868(2) 0.24189(16) 0.89013(11) 0.0520(4) Uani 1 1 d . . . H3A H 0.5553 0.2636 0.9490 0.062 Uiso 1 1 calc R . . H3B H 0.5520 0.1691 0.8798 0.062 Uiso 1 1 calc R . . C4 C 0.51984(18) 0.31755(13) 0.82126(9) 0.0388(3) Uani 1 1 d . . . H4 H 0.5636 0.3887 0.8312 0.047 Uiso 1 1 calc R . . C5 C 0.56476(16) 0.28223(11) 0.72527(9) 0.0304(3) Uani 1 1 d . . . C6 C 0.50900(13) 0.36741(11) 0.65667(8) 0.0274(3) Uani 1 1 d . . . H6 H 0.5132 0.4377 0.6864 0.033 Uiso 1 1 calc R . . C7 C 0.60332(13) 0.37643(11) 0.57450(9) 0.0277(3) Uani 1 1 d . . . C8 C 0.75973(14) 0.33283(12) 0.56912(9) 0.0309(3) Uani 1 1 d . . . C9 C 0.78780(17) 0.23940(13) 0.62911(10) 0.0364(3) Uani 1 1 d . . . H9A H 0.8911 0.2216 0.6306 0.044 Uiso 1 1 calc R . . H9B H 0.7330 0.1764 0.6102 0.044 Uiso 1 1 calc R . . C10 C 0.73492(16) 0.27943(11) 0.72017(9) 0.0319(3) Uani 1 1 d . . . C11 C 0.58326(15) 0.43374(12) 0.50026(9) 0.0318(3) Uani 1 1 d . . . C12 C 0.72929(17) 0.42891(13) 0.45297(10) 0.0376(3) Uani 1 1 d . . . H12 H 0.7260 0.4453 0.3893 0.045 Uiso 1 1 calc R . . C13 C 0.46199(18) 0.50338(14) 0.46806(12) 0.0435(4) Uani 1 1 d . . . H13A H 0.3795 0.4963 0.5071 0.065 Uiso 1 1 calc R . . H13B H 0.4345 0.4816 0.4092 0.065 Uiso 1 1 calc R . . H13C H 0.4937 0.5772 0.4671 0.065 Uiso 1 1 calc R . . C14 C 0.4995(2) 0.17053(12) 0.70261(10) 0.0428(4) Uani 1 1 d . . . H14A H 0.3981 0.1690 0.7190 0.064 Uiso 1 1 calc R . . H14B H 0.5513 0.1157 0.7348 0.064 Uiso 1 1 calc R . . H14C H 0.5088 0.1575 0.6400 0.064 Uiso 1 1 calc R . . C15 C 0.3547(2) 0.3304(2) 0.83590(13) 0.0591(5) Uani 1 1 d . . . H15A H 0.3155 0.3787 0.7922 0.089 Uiso 1 1 calc R . . H15B H 0.3373 0.3591 0.8941 0.089 Uiso 1 1 calc R . . H15C H 0.3080 0.2613 0.8306 0.089 Uiso 1 1 calc R . . C16 C 0.83431(17) 0.50126(14) 0.50864(11) 0.0424(4) Uani 1 1 d . . . H16A H 0.9234 0.5175 0.4763 0.051 Uiso 1 1 calc R . . H16B H 0.7874 0.5681 0.5264 0.051 Uiso 1 1 calc R . . C17 C 0.86453(15) 0.42763(13) 0.58933(10) 0.0346(3) Uani 1 1 d . A . C18 C 0.82900(15) 0.46775(13) 0.68152(10) 0.0337(3) Uani 1 1 d . . . C19 C 1.02646(17) 0.39204(19) 0.58988(12) 0.0524(4) Uani 1 1 d . . . H19B H 1.0435 0.3473 0.6417 0.063 Uiso 0.56 1 calc PR A 1 H19A H 1.0448 0.3481 0.5377 0.063 Uiso 0.56 1 calc PR A 1 H19D H 1.0370 0.3272 0.5544 0.063 Uiso 0.44 1 calc PR A 2 H19C H 1.0858 0.4481 0.5630 0.063 Uiso 0.44 1 calc PR A 2 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 0.0883(11) 0.0487(7) 0.0615(8) 0.0062(6) -0.0174(8) 0.0238(7) O2 0.0204(5) 0.0467(6) 0.0424(5) -0.0080(4) -0.0011(4) 0.0006(4) O3 0.0373(5) 0.0506(6) 0.0276(5) -0.0040(4) 0.0042(4) 0.0123(5) O4 0.0303(5) 0.0446(6) 0.0299(5) -0.0057(4) -0.0023(4) -0.0071(4) O5 0.0647(8) 0.0433(6) 0.0531(7) -0.0077(5) 0.0107(6) -0.0018(6) O6A 0.0291(9) 0.0512(11) 0.0710(14) -0.0115(11) 0.0009(10) -0.0041(9) O6B 0.0158(9) 0.111(3) 0.0455(13) 0.0002(16) 0.0013(10) 0.0123(13) C1 0.0473(9) 0.0545(9) 0.0404(8) 0.0053(7) -0.0125(7) 0.0104(8) C2 0.0667(12) 0.0638(11) 0.0331(8) 0.0078(7) -0.0152(8) 0.0023(9) C3 0.0676(12) 0.0578(10) 0.0304(7) 0.0047(7) 0.0009(8) -0.0086(9) C4 0.0418(8) 0.0455(8) 0.0290(6) -0.0021(6) 0.0043(6) -0.0079(7) C5 0.0300(7) 0.0319(6) 0.0291(6) -0.0019(5) -0.0015(5) -0.0030(5) C6 0.0212(6) 0.0320(6) 0.0290(6) -0.0045(5) -0.0005(5) -0.0005(5) C7 0.0219(6) 0.0322(6) 0.0291(6) -0.0030(5) -0.0023(5) 0.0014(5) C8 0.0242(6) 0.0414(7) 0.0270(6) -0.0040(6) 0.0018(5) 0.0071(5) C9 0.0331(7) 0.0406(8) 0.0356(7) -0.0030(6) -0.0022(6) 0.0137(6) C10 0.0312(7) 0.0350(7) 0.0293(6) -0.0001(5) -0.0046(5) 0.0032(5) C11 0.0272(6) 0.0368(7) 0.0314(6) -0.0020(5) -0.0034(5) 0.0014(5) C12 0.0371(7) 0.0475(8) 0.0282(6) 0.0031(6) 0.0021(6) 0.0054(6) C13 0.0396(8) 0.0453(8) 0.0456(8) 0.0027(7) -0.0105(7) 0.0068(7) C14 0.0503(9) 0.0365(7) 0.0417(7) 0.0010(7) -0.0066(7) -0.0098(7) C15 0.0463(10) 0.0858(14) 0.0453(9) -0.0051(10) 0.0168(8) -0.0058(10) C16 0.0342(7) 0.0560(9) 0.0370(8) 0.0080(7) 0.0039(6) -0.0073(7) C17 0.0224(6) 0.0484(8) 0.0329(7) -0.0015(6) 0.0029(5) 0.0015(6) C18 0.0231(6) 0.0411(7) 0.0368(7) -0.0017(6) -0.0003(5) -0.0003(5) C19 0.0228(7) 0.0875(13) 0.0469(8) -0.0081(9) 0.0027(6) 0.0062(8) 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 C1 O1 H1 109.5 C6 O2 H2 109.5 C8 O3 C12 95.23(10) C18 O4 C10 127.64(11) C19 O6A H6A 109.5 C19 O6B H6B 109.5 O1 C1 H1A 108.5 O1 C1 C2 111.74(17) O1 C1 C10 107.02(14) C2 C1 H1A 108.5 C2 C1 C10 112.54(15) C10 C1 H1A 108.5 C1 C2 H2A 109.0 C1 C2 H2B 109.0 C1 C2 C3 112.81(15) H2A C2 H2B 107.8 C3 C2 H2A 109.0 C3 C2 H2B 109.0 C2 C3 H3A 109.3 C2 C3 H3B 109.3 C2 C3 C4 111.52(15) H3A C3 H3B 108.0 C4 C3 H3A 109.3 C4 C3 H3B 109.3 C3 C4 H4 106.6 C3 C4 C5 110.51(14) C3 C4 C15 111.13(15) C5 C4 H4 106.6 C15 C4 H4 106.6 C15 C4 C5 114.83(13) C6 C5 C4 109.62(11) C10 C5 C4 108.28(11) C10 C5 C6 107.94(11) C14 C5 C4 110.70(12) C14 C5 C6 109.50(11) C14 C5 C10 110.74(13) O2 C6 C5 112.88(11) O2 C6 H6 106.6 O2 C6 C7 109.73(10) C5 C6 H6 106.6 C7 C6 C5 113.89(11) C7 C6 H6 106.6 C6 C7 C8 123.35(11) C11 C7 C6 130.18(12) C11 C7 C8 105.75(11) O3 C8 C7 102.11(11) O3 C8 C9 119.76(12) O3 C8 C17 100.97(11) C7 C8 C17 107.44(11) C9 C8 C7 113.76(11) C9 C8 C17 111.39(12) C8 C9 H9A 111.0 C8 C9 H9B 111.0 C8 C9 C10 103.63(11) H9A C9 H9B 109.0 C10 C9 H9A 111.0 C10 C9 H9B 111.0 O4 C10 C1 101.90(12) O4 C10 C5 104.97(11) O4 C10 C9 112.83(12) C1 C10 C5 115.44(13) C9 C10 C1 109.87(12) C9 C10 C5 111.43(12) C7 C11 C12 104.56(12) C7 C11 C13 133.12(14) C13 C11 C12 121.80(14) O3 C12 C11 102.17(12) O3 C12 H12 115.1 O3 C12 C16 102.05(12) C11 C12 H12 115.1 C11 C12 C16 105.50(12) C16 C12 H12 115.1 C11 C13 H13A 109.5 C11 C13 H13B 109.5 C11 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C5 C14 H14A 109.5 C5 C14 H14B 109.5 C5 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C4 C15 H15A 109.5 C4 C15 H15B 109.5 C4 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C12 C16 H16A 111.5 C12 C16 H16B 111.5 H16A C16 H16B 109.4 C17 C16 C12 101.13(12) C17 C16 H16A 111.5 C17 C16 H16B 111.5 C16 C17 C8 100.59(12) C18 C17 C8 107.34(11) C18 C17 C16 119.34(13) C18 C17 C19 107.17(12) C19 C17 C8 112.18(13) C19 C17 C16 110.15(13) O4 C18 C17 115.93(13) O5 C18 O4 118.05(14) O5 C18 C17 125.92(15) O6A C19 O6B 84.9(2) O6A C19 C17 114.09(19) O6A C19 H19B 108.7 O6A C19 H19A 108.7 O6A C19 H19D 124.7 O6A C19 H19C 25.4 O6B C19 C17 111.95(16) O6B C19 H19B 25.7 O6B C19 H19A 126.3 O6B C19 H19D 109.2 O6B C19 H19C 109.2 C17 C19 H19B 108.7 C17 C19 H19A 108.7 C17 C19 H19D 109.2 C17 C19 H19C 109.2 H19B C19 H19A 107.6 H19B C19 H19D 87.4 H19B C19 H19C 131.0 H19A C19 H19D 21.8 H19A C19 H19C 88.1 H19D C19 H19C 107.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1 0.8200 O1 C1 1.430(2) O2 H2 0.8200 O2 C6 1.4280(15) O3 C8 1.4356(16) O3 C12 1.4538(19) O4 C10 1.4954(17) O4 C18 1.3512(19) O5 C18 1.204(2) O6A H6A 0.8200 O6A C19 1.271(3) O6B H6B 0.8200 O6B C19 1.339(3) C1 H1A 0.9800 C1 C2 1.516(3) C1 C10 1.542(2) C2 H2A 0.9700 C2 H2B 0.9700 C2 C3 1.520(3) C3 H3A 0.9700 C3 H3B 0.9700 C3 C4 1.526(2) C4 H4 0.9800 C4 C5 1.5651(18) C4 C15 1.533(2) C5 C6 1.5627(19) C5 C10 1.5576(19) C5 C14 1.546(2) C6 H6 0.9800 C6 C7 1.5121(17) C7 C8 1.5306(17) C7 C11 1.337(2) C8 C9 1.491(2) C8 C17 1.546(2) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.5362(19) C11 C12 1.5140(19) C11 C13 1.486(2) C12 H12 0.9800 C12 C16 1.559(2) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C16 H16A 0.9700 C16 H16B 0.9700 C16 C17 1.545(2) C17 C18 1.510(2) C17 C19 1.544(2) C19 H19B 0.9700 C19 H19A 0.9700 C19 H19D 0.9700 C19 H19C 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 O1 C1 C2 C3 -72.3(2) O1 C1 C10 O4 -170.90(14) O1 C1 C10 C5 75.98(18) O1 C1 C10 C9 -51.04(19) O2 C6 C7 C8 -144.52(12) O2 C6 C7 C11 46.66(19) O3 C8 C9 C10 -172.84(12) O3 C8 C17 C16 41.07(13) O3 C8 C17 C18 166.55(11) O3 C8 C17 C19 -75.98(14) O3 C12 C16 C17 -31.17(14) C1 C2 C3 C4 -56.1(2) C2 C1 C10 O4 65.98(18) C2 C1 C10 C5 -47.1(2) C2 C1 C10 C9 -174.16(15) C2 C3 C4 C5 60.78(19) C2 C3 C4 C15 -170.51(17) C3 C4 C5 C6 -174.07(13) C3 C4 C5 C10 -56.53(17) C3 C4 C5 C14 65.03(17) C4 C5 C6 O2 -83.64(13) C4 C5 C6 C7 150.36(11) C4 C5 C10 O4 -60.63(13) C4 C5 C10 C1 50.69(17) C4 C5 C10 C9 176.92(12) C5 C6 C7 C8 -16.89(17) C5 C6 C7 C11 174.30(13) C6 C5 C10 O4 57.97(13) C6 C5 C10 C1 169.29(12) C6 C5 C10 C9 -64.47(14) C6 C7 C8 O3 158.24(12) C6 C7 C8 C9 27.76(18) C6 C7 C8 C17 -96.02(14) C6 C7 C11 C12 167.64(13) C6 C7 C11 C13 -3.9(3) C7 C8 C9 C10 -51.79(15) C7 C8 C17 C16 -65.48(13) C7 C8 C17 C18 60.01(14) C7 C8 C17 C19 177.48(12) C7 C11 C12 O3 34.81(14) C7 C11 C12 C16 -71.53(14) C8 O3 C12 C11 -51.80(12) C8 O3 C12 C16 57.20(12) C8 C7 C11 C12 -2.66(14) C8 C7 C11 C13 -174.23(16) C8 C9 C10 O4 -43.53(15) C8 C9 C10 C1 -156.49(13) C8 C9 C10 C5 74.27(14) C8 C17 C18 O4 32.50(16) C8 C17 C18 O5 -151.24(16) C8 C17 C19 O6A 168.34(18) C8 C17 C19 O6B -97.4(3) C9 C8 C17 C16 169.30(12) C9 C8 C17 C18 -65.21(14) C9 C8 C17 C19 52.26(16) C10 O4 C18 O5 170.91(14) C10 O4 C18 C17 -12.52(19) C10 C1 C2 C3 48.1(2) C10 C5 C6 O2 158.61(11) C10 C5 C6 C7 32.61(15) C11 C7 C8 O3 -30.62(14) C11 C7 C8 C9 -161.10(12) C11 C7 C8 C17 75.12(13) C11 C12 C16 C17 75.27(14) C12 O3 C8 C7 49.63(12) C12 O3 C8 C9 176.32(13) C12 O3 C8 C17 -61.09(12) C12 C16 C17 C8 -5.38(14) C12 C16 C17 C18 -122.30(14) C12 C16 C17 C19 113.16(14) C13 C11 C12 O3 -152.42(13) C13 C11 C12 C16 101.23(16) C14 C5 C6 O2 37.98(15) C14 C5 C6 C7 -88.02(14) C14 C5 C10 O4 177.82(11) C14 C5 C10 C1 -70.85(16) C14 C5 C10 C9 55.38(15) C15 C4 C5 C6 59.26(18) C15 C4 C5 C10 176.80(15) C15 C4 C5 C14 -61.64(19) C16 C17 C18 O4 145.85(13) C16 C17 C18 O5 -37.9(2) C16 C17 C19 O6A 57.2(2) C16 C17 C19 O6B 151.4(2) C17 C8 C9 C10 69.82(14) C18 O4 C10 C1 136.08(14) C18 O4 C10 C5 -103.20(14) C18 O4 C10 C9 18.33(18) C18 C17 C19 O6A -74.1(2) C18 C17 C19 O6B 20.2(3) C19 C17 C18 O4 -88.19(16) C19 C17 C18 O5 88.1(2)