#------------------------------------------------------------------------------ #$Date: 2023-11-22 04:11:29 +0200 (Wed, 22 Nov 2023) $ #$Revision: 287717 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247759.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_7247759 loop_ _publ_author_name 'Cardoso, Luanny M. B.' 'de Oliveira Neto, Jo\~ao G.' 'Saraiva, Gilberto D.' 'Leite, F\'abio F.' 'Ayala, Alejandro P.' 'dos Santos, Adenilson O.' 'de Sousa, Francisco F.' _publ_section_title ; New polymorphic phase of arachidic acid crystal: structure, intermolecular interactions, low-temperature stability and Raman spectroscopy combined with DFT calculations ; _journal_issue 48 _journal_name_full 'RSC Advances' _journal_page_first 34032 _journal_page_last 34044 _journal_paper_doi 10.1039/D3RA05388A _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C20 H40 O2' _chemical_formula_sum 'C20 H40 O2' _chemical_formula_weight 312.52 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-05-30 _audit_creation_method ; FinalCif V105 by Daniel Kratzert, Freiburg 2022, https://dkratzert.de/finalcif.html ; _audit_update_record ; 2022-06-05 deposited with the CCDC. 2023-11-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.785(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 48.445(7) _cell_length_b 7.1499(10) _cell_length_c 5.5267(8) _cell_measurement_reflns_used 4383 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.51 _cell_measurement_theta_min 2.94 _cell_volume 1912.1(5) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_collection 'Bruker BIS V6.2.14/2020-04-30' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100 _diffrn_detector HPAD _diffrn_detector_area_resol_mean 7.39 _diffrn_detector_type 'Bruker PHOTON II CPAD Area Detector' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\w and \f scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_unetI/netI 0.0508 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_h_min -63 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 24532 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.996 _diffrn_reflns_theta_min 2.526 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_type 'Incoatec I\ms HB' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_T_max 0.7468 _exptl_absorpt_correction_T_min 0.6066 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1119 before and 0.0727 after correction. The Ratio of minimum to maximum transmission is 0.8123. The \l/2 correction factor is Not present. ; _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 1.086 _exptl_crystal_description plate _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.615 _exptl_crystal_size_mid 0.387 _exptl_crystal_size_min 0.058 _refine_diff_density_max 0.370 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 4601 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0684 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+0.9663P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1902 _refine_ls_wR_factor_ref 0.2135 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3224 _reflns_number_total 4601 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra05388a2.cif _cod_data_source_block arach _cod_original_cell_volume 1912.0(5) _cod_database_code 7247759 _shelx_shelxl_version_number 2018/3 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C6(H6A,H6B), C2(H2A,H2B), C8(H8A,H8B), C5(H5A,H5B), C7(H7A,H7B), C3(H3A,H3B), C10(H10A,H10B), C12(H12A,H12B), C9(H9A,H9B), C13(H13A,H13B), C11(H11A,H11B), C15(H15A,H15B), C14(H14A,H14B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B) 2.b Idealised Me refined as rotating group: C20(H20A,H20B,H20C) 2.c Idealised tetrahedral OH refined as rotating group: O2(H2) ; _olex2_submission_special_instructions 'No special instructions were received' _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 0.960 _shelx_estimated_absorpt_t_max 0.996 _olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800' _shelx_res_file ; TITL mo_220530_araq_nico_0ma_a.res in P2(1)/c mo_220530_araq_nico_0ma.res created by SHELXL-2018/3 at 14:13:08 on 30-May-2022 REM Old TITL mo_220530_ARAQ_NICO_0ma in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.151, Rweak 0.005, Alpha 0.072 REM 0.515 for 316 systematic absences, Orientation as input REM Formula found by SHELXT: C20 O2 CELL 0.71073 48.4447 7.1499 5.5267 90 92.785 90 ZERR 4 0.0065 0.001 0.0008 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 80 160 8 L.S. 4 PLAN 7 0 0 SIZE 0.058 0.387 0.615 TEMP -173.15 CONF BOND list 4 fmap 2 MORE -1 ACTA BOND $H OMIT -3 56 OMIT 1 2 0 OMIT -12 3 3 OMIT 0 6 0 OMIT 6 6 3 OMIT 1 8 0 REM REM REM WGHT 0.094200 0.966300 FVAR 0.51733 O1 3 0.467517 0.421090 1.038604 11.00000 0.02029 0.01863 = 0.01776 -0.00513 0.00043 0.00024 O2 3 0.491416 0.634155 1.261168 11.00000 0.01865 0.02242 = 0.01819 -0.00417 0.00274 -0.00396 AFIX 147 H2 2 0.503463 0.612561 1.160492 11.00000 -1.50000 AFIX 0 C1 1 0.469650 0.526250 1.213390 11.00000 0.01784 0.01537 = 0.01604 0.00276 -0.00242 0.00130 C4 1 0.403726 0.539797 1.126521 11.00000 0.01395 0.01580 = 0.01756 0.00027 -0.00052 0.00027 AFIX 23 H4A 2 0.402104 0.675602 1.157742 11.00000 -1.20000 H4B 2 0.413538 0.523802 0.974879 11.00000 -1.20000 AFIX 0 C6 1 0.357352 0.541785 0.883621 11.00000 0.01424 0.01679 = 0.01689 0.00085 -0.00128 -0.00081 AFIX 23 H6A 2 0.355855 0.678245 0.910370 11.00000 -1.20000 H6B 2 0.366859 0.522486 0.731027 11.00000 -1.20000 AFIX 0 C2 1 0.448243 0.546190 1.398891 11.00000 0.01583 0.02290 = 0.01346 -0.00134 -0.00164 -0.00033 AFIX 23 H2A 2 0.444656 0.681041 1.423172 11.00000 -1.20000 H2B 2 0.455906 0.495336 1.554661 11.00000 -1.20000 AFIX 0 C8 1 0.310700 0.542357 0.646340 11.00000 0.01543 0.01699 = 0.01511 0.00077 -0.00161 -0.00048 AFIX 23 H8A 2 0.309164 0.679019 0.671159 11.00000 -1.20000 H8B 2 0.320135 0.521928 0.493623 11.00000 -1.20000 AFIX 0 C5 1 0.374849 0.455832 1.093028 11.00000 0.01525 0.01734 = 0.01505 0.00102 -0.00014 0.00014 AFIX 23 H5A 2 0.365091 0.472775 1.244782 11.00000 -1.20000 H5B 2 0.376580 0.319749 1.064372 11.00000 -1.20000 AFIX 0 C7 1 0.328364 0.458692 0.856112 11.00000 0.01453 0.01786 = 0.01634 0.00061 -0.00042 -0.00026 AFIX 23 H7A 2 0.318864 0.478698 1.008587 11.00000 -1.20000 H7B 2 0.329911 0.322080 0.830900 11.00000 -1.20000 AFIX 0 C3 1 0.420800 0.449212 1.336097 11.00000 0.01548 0.02056 = 0.01396 0.00190 0.00075 0.00015 AFIX 23 H3A 2 0.409668 0.448701 1.481652 11.00000 -1.20000 H3B 2 0.424522 0.317414 1.293496 11.00000 -1.20000 AFIX 0 C10 1 0.263942 0.541663 0.411272 11.00000 0.01542 0.01668 = 0.01471 0.00120 -0.00149 0.00036 AFIX 23 H10A 2 0.262450 0.678437 0.435288 11.00000 -1.20000 H10B 2 0.273303 0.520623 0.258322 11.00000 -1.20000 AFIX 0 C12 1 0.217179 0.541751 0.177434 11.00000 0.01677 0.01768 = 0.01401 0.00094 -0.00102 -0.00028 AFIX 23 H12A 2 0.226495 0.520438 0.024321 11.00000 -1.20000 H12B 2 0.215730 0.678560 0.201347 11.00000 -1.20000 AFIX 0 C9 1 0.281739 0.458883 0.620795 11.00000 0.01462 0.01745 = 0.01599 0.00019 -0.00203 0.00063 AFIX 23 H9A 2 0.272329 0.479362 0.773627 11.00000 -1.20000 H9B 2 0.283303 0.322196 0.596343 11.00000 -1.20000 AFIX 0 C13 1 0.188110 0.458869 0.153752 11.00000 0.01719 0.01692 = 0.01373 0.00097 -0.00192 -0.00025 AFIX 23 H13A 2 0.189553 0.322078 0.129645 11.00000 -1.20000 H13B 2 0.178794 0.480087 0.306889 11.00000 -1.20000 AFIX 0 C11 1 0.234947 0.458781 0.386638 11.00000 0.01621 0.01739 = 0.01547 0.00048 -0.00156 0.00009 AFIX 23 H11A 2 0.225588 0.479700 0.539628 11.00000 -1.20000 H11B 2 0.236434 0.322028 0.362400 11.00000 -1.20000 AFIX 0 C15 1 0.141258 0.458953 -0.078788 11.00000 0.01771 0.01650 = 0.01495 0.00099 -0.00170 -0.00052 AFIX 23 H15A 2 0.142725 0.322244 -0.103526 11.00000 -1.20000 H15B 2 0.132005 0.479597 0.074788 11.00000 -1.20000 AFIX 0 C14 1 0.170366 0.542074 -0.055301 11.00000 0.01679 0.01789 = 0.01430 0.00148 -0.00158 -0.00061 AFIX 23 H14A 2 0.179676 0.520834 -0.208465 11.00000 -1.20000 H14B 2 0.168919 0.678865 -0.031221 11.00000 -1.20000 AFIX 0 C17 1 0.094311 0.458887 -0.308066 11.00000 0.01974 0.01761 = 0.01580 0.00128 -0.00184 -0.00049 AFIX 23 H17A 2 0.095805 0.322126 -0.332202 11.00000 -1.20000 H17B 2 0.085192 0.479825 -0.153904 11.00000 -1.20000 AFIX 0 C16 1 0.123362 0.542282 -0.286819 11.00000 0.01729 0.01880 = 0.01515 0.00233 -0.00108 -0.00002 AFIX 23 H16A 2 0.132538 0.521130 -0.440656 11.00000 -1.20000 H16B 2 0.121912 0.679051 -0.262546 11.00000 -1.20000 AFIX 0 C18 1 0.076212 0.541082 -0.514983 11.00000 0.01914 0.02143 = 0.01692 0.00137 -0.00185 0.00060 AFIX 23 H18A 2 0.085401 0.521374 -0.669072 11.00000 -1.20000 H18B 2 0.074508 0.677620 -0.489945 11.00000 -1.20000 AFIX 0 C19 1 0.047336 0.455480 -0.536677 11.00000 0.02126 0.02565 = 0.01935 0.00185 -0.00210 -0.00026 AFIX 23 H19A 2 0.038247 0.473834 -0.381828 11.00000 -1.20000 H19B 2 0.049050 0.319162 -0.563546 11.00000 -1.20000 AFIX 0 C20 1 0.029024 0.538935 -0.741807 11.00000 0.02244 0.03710 = 0.02453 0.00069 -0.00560 0.00135 AFIX 137 H20A 2 0.037712 0.519611 -0.896322 11.00000 -1.50000 H20B 2 0.026686 0.673231 -0.713851 11.00000 -1.50000 H20C 2 0.010919 0.477535 -0.746930 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_220530_araq_nico_0ma_a.res in P2(1)/c REM wR2 = 0.213543, GooF = S = 1.09588, Restrained GooF = 1.09588 for all data REM R1 = 0.068368 for 3224 Fo > 4sig(Fo) and 0.096810 for all 4601 data REM 201 parameters refined using 0 restraints END WGHT 0.0942 0.9663 REM Highest difference peak 0.370, deepest hole -0.340, 1-sigma level 0.061 Q1 1 0.2720 0.4983 0.5317 11.00000 0.05 0.37 Q2 1 0.2239 0.4841 0.2789 11.00000 0.05 0.36 Q3 1 0.2968 0.4969 0.6242 11.00000 0.05 0.33 Q4 1 0.3433 0.5079 0.8683 11.00000 0.05 0.32 Q5 1 0.1575 0.4882 -0.0743 11.00000 0.05 0.32 Q6 1 0.2514 0.4792 0.3792 11.00000 0.05 0.32 Q7 1 0.1088 0.5006 -0.2817 11.00000 0.05 0.31 ; _shelx_res_checksum 15733 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.46752(2) 0.42109(17) 1.0386(2) 0.0189(3) Uani 1 1 d . . . . . O2 O 0.49142(2) 0.63416(17) 1.2612(2) 0.0197(3) Uani 1 1 d . . . . . H2 H 0.503463 0.612561 1.160492 0.030 Uiso 1 1 calc R U . . . C1 C 0.46965(3) 0.5263(2) 1.2134(3) 0.0165(4) Uani 1 1 d . . . . . C4 C 0.40373(3) 0.5398(2) 1.1265(3) 0.0158(4) Uani 1 1 d . . . . . H4A H 0.402104 0.675602 1.157742 0.019 Uiso 1 1 calc R U . . . H4B H 0.413538 0.523802 0.974879 0.019 Uiso 1 1 calc R U . . . C6 C 0.35735(3) 0.5418(2) 0.8836(3) 0.0160(4) Uani 1 1 d . . . . . H6A H 0.355855 0.678245 0.910370 0.019 Uiso 1 1 calc R U . . . H6B H 0.366859 0.522486 0.731027 0.019 Uiso 1 1 calc R U . . . C2 C 0.44824(3) 0.5462(2) 1.3989(3) 0.0175(4) Uani 1 1 d . . . . . H2A H 0.444656 0.681041 1.423172 0.021 Uiso 1 1 calc R U . . . H2B H 0.455906 0.495336 1.554661 0.021 Uiso 1 1 calc R U . . . C8 C 0.31070(3) 0.5424(2) 0.6463(3) 0.0159(4) Uani 1 1 d . . . . . H8A H 0.309164 0.679019 0.671159 0.019 Uiso 1 1 calc R U . . . H8B H 0.320135 0.521928 0.493623 0.019 Uiso 1 1 calc R U . . . C5 C 0.37485(3) 0.4558(2) 1.0930(3) 0.0159(4) Uani 1 1 d . . . . . H5A H 0.365091 0.472775 1.244782 0.019 Uiso 1 1 calc R U . . . H5B H 0.376580 0.319749 1.064372 0.019 Uiso 1 1 calc R U . . . C7 C 0.32836(3) 0.4587(2) 0.8561(3) 0.0163(4) Uani 1 1 d . . . . . H7A H 0.318864 0.478698 1.008587 0.020 Uiso 1 1 calc R U . . . H7B H 0.329911 0.322080 0.830900 0.020 Uiso 1 1 calc R U . . . C3 C 0.42080(3) 0.4492(2) 1.3361(3) 0.0167(4) Uani 1 1 d . . . . . H3A H 0.409668 0.448701 1.481652 0.020 Uiso 1 1 calc R U . . . H3B H 0.424522 0.317414 1.293496 0.020 Uiso 1 1 calc R U . . . C10 C 0.26394(3) 0.5417(2) 0.4113(3) 0.0157(4) Uani 1 1 d . . . . . H10A H 0.262450 0.678437 0.435288 0.019 Uiso 1 1 calc R U . . . H10B H 0.273303 0.520623 0.258322 0.019 Uiso 1 1 calc R U . . . C12 C 0.21718(3) 0.5418(2) 0.1774(3) 0.0162(4) Uani 1 1 d . . . . . H12A H 0.226495 0.520438 0.024321 0.019 Uiso 1 1 calc R U . . . H12B H 0.215730 0.678560 0.201347 0.019 Uiso 1 1 calc R U . . . C9 C 0.28174(3) 0.4589(2) 0.6208(3) 0.0161(4) Uani 1 1 d . . . . . H9A H 0.272329 0.479362 0.773627 0.019 Uiso 1 1 calc R U . . . H9B H 0.283303 0.322196 0.596343 0.019 Uiso 1 1 calc R U . . . C13 C 0.18811(3) 0.4589(2) 0.1538(3) 0.0160(4) Uani 1 1 d . . . . . H13A H 0.189553 0.322078 0.129645 0.019 Uiso 1 1 calc R U . . . H13B H 0.178794 0.480087 0.306889 0.019 Uiso 1 1 calc R U . . . C11 C 0.23495(3) 0.4588(2) 0.3866(3) 0.0164(4) Uani 1 1 d . . . . . H11A H 0.225588 0.479700 0.539628 0.020 Uiso 1 1 calc R U . . . H11B H 0.236434 0.322028 0.362400 0.020 Uiso 1 1 calc R U . . . C15 C 0.14126(3) 0.4590(2) -0.0788(3) 0.0165(4) Uani 1 1 d . . . . . H15A H 0.142725 0.322244 -0.103526 0.020 Uiso 1 1 calc R U . . . H15B H 0.132005 0.479597 0.074788 0.020 Uiso 1 1 calc R U . . . C14 C 0.17037(3) 0.5421(2) -0.0553(3) 0.0164(4) Uani 1 1 d . . . . . H14A H 0.179676 0.520834 -0.208465 0.020 Uiso 1 1 calc R U . . . H14B H 0.168919 0.678865 -0.031221 0.020 Uiso 1 1 calc R U . . . C17 C 0.09431(4) 0.4589(2) -0.3081(3) 0.0178(4) Uani 1 1 d . . . . . H17A H 0.095805 0.322126 -0.332202 0.021 Uiso 1 1 calc R U . . . H17B H 0.085192 0.479825 -0.153904 0.021 Uiso 1 1 calc R U . . . C16 C 0.12336(3) 0.5423(2) -0.2868(3) 0.0171(4) Uani 1 1 d . . . . . H16A H 0.132538 0.521130 -0.440656 0.021 Uiso 1 1 calc R U . . . H16B H 0.121912 0.679051 -0.262546 0.021 Uiso 1 1 calc R U . . . C18 C 0.07621(4) 0.5411(2) -0.5150(3) 0.0193(4) Uani 1 1 d . . . . . H18A H 0.085401 0.521374 -0.669072 0.023 Uiso 1 1 calc R U . . . H18B H 0.074508 0.677620 -0.489945 0.023 Uiso 1 1 calc R U . . . C19 C 0.04734(4) 0.4555(3) -0.5367(3) 0.0222(4) Uani 1 1 d . . . . . H19A H 0.038247 0.473834 -0.381828 0.027 Uiso 1 1 calc R U . . . H19B H 0.049050 0.319162 -0.563546 0.027 Uiso 1 1 calc R U . . . C20 C 0.02902(4) 0.5389(3) -0.7418(4) 0.0282(5) Uani 1 1 d . . . . . H20A H 0.037712 0.519611 -0.896322 0.042 Uiso 1 1 calc R U . . . H20B H 0.026686 0.673231 -0.713851 0.042 Uiso 1 1 calc R U . . . H20C H 0.010919 0.477535 -0.746930 0.042 Uiso 1 1 calc R U . . . 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 0.0203(6) 0.0186(6) 0.0178(7) -0.0051(5) 0.0004(5) 0.0002(5) O2 0.0187(6) 0.0224(7) 0.0182(7) -0.0042(5) 0.0027(5) -0.0040(5) C1 0.0178(9) 0.0154(8) 0.0160(9) 0.0028(6) -0.0024(6) 0.0013(6) C4 0.0139(8) 0.0158(8) 0.0176(9) 0.0003(6) -0.0005(6) 0.0003(6) C6 0.0142(8) 0.0168(9) 0.0169(9) 0.0008(6) -0.0013(6) -0.0008(6) C2 0.0158(8) 0.0229(9) 0.0135(8) -0.0013(7) -0.0016(6) -0.0003(6) C8 0.0154(8) 0.0170(9) 0.0151(9) 0.0008(6) -0.0016(6) -0.0005(6) C5 0.0152(8) 0.0173(9) 0.0150(8) 0.0010(6) -0.0001(6) 0.0001(6) C7 0.0145(8) 0.0179(9) 0.0163(9) 0.0006(6) -0.0004(6) -0.0003(6) C3 0.0155(8) 0.0206(9) 0.0140(9) 0.0019(6) 0.0007(6) 0.0002(6) C10 0.0154(8) 0.0167(9) 0.0147(8) 0.0012(6) -0.0015(6) 0.0004(6) C12 0.0168(8) 0.0177(9) 0.0140(9) 0.0009(6) -0.0010(6) -0.0003(6) C9 0.0146(8) 0.0175(9) 0.0160(9) 0.0002(6) -0.0020(6) 0.0006(6) C13 0.0172(8) 0.0169(9) 0.0137(9) 0.0010(6) -0.0019(6) -0.0002(6) C11 0.0162(8) 0.0174(9) 0.0155(9) 0.0005(6) -0.0016(6) 0.0001(6) C15 0.0177(8) 0.0165(9) 0.0150(9) 0.0010(6) -0.0017(6) -0.0005(6) C14 0.0168(8) 0.0179(9) 0.0143(9) 0.0015(6) -0.0016(6) -0.0006(6) C17 0.0197(9) 0.0176(9) 0.0158(9) 0.0013(7) -0.0018(7) -0.0005(6) C16 0.0173(8) 0.0188(9) 0.0151(9) 0.0023(6) -0.0011(6) 0.0000(6) C18 0.0191(9) 0.0214(9) 0.0169(9) 0.0014(7) -0.0019(7) 0.0006(7) C19 0.0213(9) 0.0256(10) 0.0193(10) 0.0019(7) -0.0021(7) -0.0003(7) C20 0.0224(10) 0.0371(12) 0.0245(11) 0.0007(8) -0.0056(8) 0.0013(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 H2 109.5 . . ? O1 C1 O2 123.47(16) . . ? O1 C1 C2 124.25(15) . . ? O2 C1 C2 112.27(14) . . ? H4A C4 H4B 107.8 . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C5 C4 C3 112.53(14) . . ? C3 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? H6A C6 H6B 107.8 . . ? C5 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C7 C6 C5 113.11(14) . . ? C1 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C1 C2 C3 115.18(14) . . ? H2A C2 H2B 107.5 . . ? C3 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? H8A C8 H8B 107.7 . . ? C7 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C9 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C9 C8 C7 113.30(14) . . ? C4 C5 C6 113.88(14) . . ? C4 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C6 C7 C8 113.69(14) . . ? C6 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C4 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 C4 114.34(14) . . ? C2 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? H10A C10 H10B 107.7 . . ? C9 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C11 C10 C9 113.60(14) . . ? H12A C12 H12B 107.7 . . ? C13 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C11 C12 C13 113.42(14) . . ? C8 C9 C10 113.64(14) . . ? C8 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C12 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C14 C13 C12 113.36(14) . . ? C14 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C10 C11 C12 113.55(14) . . ? C10 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? H15A C15 H15B 107.7 . . ? C14 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C16 C15 C14 113.55(14) . . ? C13 C14 C15 113.30(14) . . ? C13 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? H17A C17 H17B 107.7 . . ? C16 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18 C17 H17A 108.8 . . ? C18 C17 H17B 108.8 . . ? C18 C17 C16 113.66(14) . . ? C15 C16 C17 113.13(14) . . ? C15 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C17 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C17 C18 C19 113.32(15) . . ? H18A C18 H18B 107.7 . . ? C19 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C18 C19 H19A 108.9 . . ? C18 C19 H19B 108.9 . . ? C18 C19 C20 113.51(15) . . ? H19A C19 H19B 107.7 . . ? C20 C19 H19A 108.9 . . ? C20 C19 H19B 108.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.225(2) . ? O2 H2 0.8400 . ? O2 C1 1.323(2) . ? C1 C2 1.500(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.525(2) . ? C4 C3 1.534(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C5 1.530(2) . ? C6 C7 1.526(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.524(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C7 1.529(2) . ? C8 C9 1.525(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C9 1.529(2) . ? C10 C11 1.525(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.528(2) . ? C12 C11 1.527(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.527(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C14 1.530(2) . ? C15 C16 1.527(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C16 1.528(2) . ? C17 C18 1.525(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 C19 1.526(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.527(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -9.6(2) . . . . ? O2 C1 C2 C3 171.11(14) . . . . ? C1 C2 C3 C4 -69.70(19) . . . . ? C5 C4 C3 C2 -171.96(14) . . . . ? C5 C6 C7 C8 -179.60(14) . . . . ? C7 C6 C5 C4 -178.88(13) . . . . ? C7 C8 C9 C10 -179.95(14) . . . . ? C3 C4 C5 C6 -179.42(13) . . . . ? C12 C13 C14 C15 -179.99(13) . . . . ? C9 C8 C7 C6 -179.82(14) . . . . ? C9 C10 C11 C12 179.94(14) . . . . ? C13 C12 C11 C10 -179.81(13) . . . . ? C11 C10 C9 C8 -179.72(13) . . . . ? C11 C12 C13 C14 179.95(14) . . . . ? C14 C15 C16 C17 -179.78(14) . . . . ? C17 C18 C19 C20 179.33(15) . . . . ? C16 C15 C14 C13 179.72(14) . . . . ? C16 C17 C18 C19 179.36(14) . . . . ? C18 C17 C16 C15 179.93(14) . . . . ?