#------------------------------------------------------------------------------ #$Date: 2023-11-22 04:11:29 +0200 (Wed, 22 Nov 2023) $ #$Revision: 287717 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247758.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_7247758 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 2022-06-03 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2022-06-05 deposited with the CCDC. 2023-11-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.301(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 48.478(19) _cell_length_b 7.400(3) _cell_length_c 5.597(2) _cell_measurement_reflns_used 2274 _cell_measurement_temperature 298.00 _cell_measurement_theta_max 28.68 _cell_measurement_theta_min 2.94 _cell_volume 2004.5(13) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _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 298.00 _diffrn_detector HPAD _diffrn_detector_area_resol_mean 7.39 _diffrn_detector_type 'Bruker PHOTON II CPAD Area Detector' _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.965 _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 0.0581 _diffrn_reflns_av_unetI/netI 0.0776 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.965 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_h_min -64 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 19658 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.965 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.282 _diffrn_reflns_theta_min 2.525 _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 0.064 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.5687 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1102 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.7622. 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 1.036 _exptl_crystal_description plate _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.243 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 4807 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.2057 _refine_ls_R_factor_gt 0.0950 _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^)+(0.1424P)^2^+1.1527P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2710 _refine_ls_wR_factor_ref 0.3471 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2015 _reflns_number_total 4807 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra05388a2.cif _cod_data_source_block arach_300k _cod_original_cell_volume 2004.6(13) _cod_database_code 7247758 _shelx_shelxl_version_number 2018/3 _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 0.998 _shelx_estimated_absorpt_t_min 0.994 _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), C7(H7A,H7B), C5(H5A,H5B), C9(H9A,H9B), C8(H8A,H8B), C3(H3A,H3B), C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C2(H2A,H2B), C15(H15A,H15B), 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: O1(H1) ; _shelx_res_file ; TITL mo_220530_araq_nico_300k_0ma_a.res in P2(1)/c mo_220530_araq_nico_300k_0ma.res created by SHELXL-2018/3 at 15:37:09 on 03-Jun-2022 REM Old TITL mo_220530_ARAQ_NICO_300K_0ma in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.251, Rweak 0.008, Alpha 0.076 REM 0.513 for 315 systematic absences, Orientation as input REM Formula found by SHELXT: C20 O2 CELL 0.71073 48.4783 7.4 5.5972 90 93.301 90 ZERR 4 0.0189 0.0028 0.0021 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 80 160 8 EQIV $1 1-X,1-Y,2-Z L.S. 10 PLAN 8 0 0 SIZE 0.03 0.1 0.1 TEMP 24.85 CONF HTAB O1 O2_$1 BOND list 4 MORE -1 BOND $H fmap 2 ACTA OMIT 1 2 0 REM REM REM WGHT 0.142400 1.152700 EXTI 0.007651 FVAR 0.50243 O2 3 0.467763 0.422951 1.038810 11.00000 0.05047 0.07394 = 0.05886 -0.01709 0.00872 -0.00465 O1 3 0.491072 0.630638 1.255556 11.00000 0.05456 0.07842 = 0.06233 -0.01565 0.01216 -0.01378 AFIX 147 H1 2 0.503417 0.602744 1.168389 11.00000 -1.50000 AFIX 0 C1 1 0.469587 0.525157 1.210346 11.00000 0.04176 0.05961 = 0.04889 0.00523 -0.00346 0.00287 C4 1 0.404050 0.538650 1.119450 11.00000 0.03928 0.05019 = 0.05006 -0.00056 0.00169 -0.00204 AFIX 23 H4A 2 0.413678 0.524235 0.973456 11.00000 -1.20000 H4B 2 0.402463 0.667072 1.150561 11.00000 -1.20000 AFIX 0 C6 1 0.357673 0.539950 0.875741 11.00000 0.04132 0.04985 = 0.04480 0.00171 0.00032 0.00066 AFIX 23 H6A 2 0.356211 0.669125 0.901604 11.00000 -1.20000 H6B 2 0.367046 0.521895 0.729105 11.00000 -1.20000 AFIX 0 C7 1 0.328779 0.460743 0.844336 11.00000 0.04114 0.05338 = 0.04700 0.00010 0.00062 -0.00013 AFIX 23 H7A 2 0.319419 0.479591 0.990874 11.00000 -1.20000 H7B 2 0.330301 0.331394 0.820298 11.00000 -1.20000 AFIX 0 C5 1 0.375114 0.457686 1.082856 11.00000 0.04177 0.04950 = 0.04855 0.00257 0.00318 -0.00077 AFIX 23 H5A 2 0.376821 0.328866 1.055263 11.00000 -1.20000 H5B 2 0.365520 0.473579 1.228769 11.00000 -1.20000 AFIX 0 C9 1 0.282280 0.460628 0.608575 11.00000 0.04322 0.05476 = 0.04721 0.00007 -0.00315 0.00187 AFIX 23 H9A 2 0.273055 0.480212 0.755629 11.00000 -1.20000 H9B 2 0.283807 0.331175 0.585522 11.00000 -1.20000 AFIX 0 C8 1 0.311097 0.540301 0.636692 11.00000 0.04159 0.05328 = 0.04358 0.00136 -0.00130 0.00023 AFIX 23 H8A 2 0.309597 0.669734 0.660070 11.00000 -1.20000 H8B 2 0.320347 0.520751 0.489754 11.00000 -1.20000 AFIX 0 C3 1 0.421049 0.450735 1.326086 11.00000 0.04202 0.06133 = 0.04713 0.00383 0.00626 -0.00061 AFIX 23 H3A 2 0.410174 0.450344 1.466232 11.00000 -1.20000 H3B 2 0.424564 0.325898 1.284605 11.00000 -1.20000 AFIX 0 C11 1 0.235633 0.460827 0.373064 11.00000 0.04521 0.05934 = 0.04643 -0.00203 -0.00379 0.00000 AFIX 23 H11A 2 0.226466 0.480707 0.520347 11.00000 -1.20000 H11B 2 0.237096 0.331315 0.350246 11.00000 -1.20000 AFIX 0 C10 1 0.264434 0.539550 0.400741 11.00000 0.04525 0.05367 = 0.04708 0.00367 -0.00158 -0.00104 AFIX 23 H10A 2 0.262985 0.669082 0.423439 11.00000 -1.20000 H10B 2 0.273627 0.519486 0.253632 11.00000 -1.20000 AFIX 0 C12 1 0.217731 0.539389 0.166064 11.00000 0.04565 0.06036 = 0.04513 0.00494 -0.00193 -0.00157 AFIX 23 H12A 2 0.216397 0.669033 0.188244 11.00000 -1.20000 H12B 2 0.226836 0.518673 0.018668 11.00000 -1.20000 AFIX 0 C13 1 0.188817 0.461799 0.139194 11.00000 0.04923 0.06479 = 0.04518 0.00120 -0.00382 -0.00036 AFIX 23 H13A 2 0.190192 0.332122 0.117553 11.00000 -1.20000 H13B 2 0.179748 0.482599 0.286746 11.00000 -1.20000 AFIX 0 C14 1 0.170825 0.538688 -0.066304 11.00000 0.04757 0.06765 = 0.04274 0.00504 -0.00246 0.00113 AFIX 23 H14A 2 0.169493 0.668421 -0.045010 11.00000 -1.20000 H14B 2 0.179851 0.517477 -0.213972 11.00000 -1.20000 AFIX 0 C2 1 0.448523 0.542629 1.390483 11.00000 0.04409 0.07381 = 0.04742 -0.00251 0.00154 -0.00084 AFIX 23 H2A 2 0.445120 0.670116 1.416327 11.00000 -1.20000 H2B 2 0.456062 0.492676 1.540605 11.00000 -1.20000 AFIX 0 C15 1 0.141985 0.461571 -0.092100 11.00000 0.04879 0.07300 = 0.04473 0.00249 -0.00372 0.00008 AFIX 23 H15A 2 0.133028 0.482101 0.056067 11.00000 -1.20000 H15B 2 0.143344 0.331924 -0.114132 11.00000 -1.20000 AFIX 0 C17 1 0.095085 0.461218 -0.319543 11.00000 0.05222 0.07706 = 0.05200 0.00134 -0.00434 0.00224 AFIX 23 H17A 2 0.086319 0.481493 -0.170393 11.00000 -1.20000 H17B 2 0.096481 0.331593 -0.341605 11.00000 -1.20000 AFIX 0 C16 1 0.123840 0.538355 -0.295924 11.00000 0.04733 0.07344 = 0.04740 0.00382 -0.00307 0.00099 AFIX 23 H16A 2 0.122509 0.668065 -0.274393 11.00000 -1.20000 H16B 2 0.132721 0.517282 -0.444333 11.00000 -1.20000 AFIX 0 C18 1 0.076482 0.537411 -0.522252 11.00000 0.05204 0.08238 = 0.05555 0.00086 -0.00475 0.00175 AFIX 23 H18A 2 0.074927 0.666912 -0.499812 11.00000 -1.20000 H18B 2 0.085242 0.517725 -0.671563 11.00000 -1.20000 AFIX 0 C19 1 0.047947 0.458362 -0.544369 11.00000 0.05575 0.11004 = 0.06943 0.00431 -0.00652 -0.00296 AFIX 23 H19A 2 0.039247 0.477147 -0.394571 11.00000 -1.20000 H19B 2 0.049502 0.329000 -0.568119 11.00000 -1.20000 AFIX 0 C20 1 0.029296 0.535317 -0.745246 11.00000 0.06592 0.14153 = 0.08319 0.00568 -0.01582 0.00422 AFIX 137 H20A 2 0.037389 0.514537 -0.895370 11.00000 -1.50000 H20B 2 0.027094 0.662860 -0.721428 11.00000 -1.50000 H20C 2 0.011570 0.477384 -0.746403 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_220530_araq_nico_300k_0ma_a.res in P2(1)/c REM wR2 = 0.347079, GooF = S = 1.03501, Restrained GooF = 1.03501 for all data REM R1 = 0.094989 for 2015 Fo > 4sig(Fo) and 0.205691 for all 4807 data REM 202 parameters refined using 0 restraints END WGHT 0.1424 1.1526 REM Highest difference peak 0.243, deepest hole -0.301, 1-sigma level 0.050 Q1 1 0.1732 0.5011 0.0522 11.00000 0.05 0.24 Q2 1 0.0151 0.5005 -1.0578 11.00000 0.05 0.24 Q3 1 0.3643 0.5200 0.9952 11.00000 0.05 0.23 Q4 1 0.3159 0.5088 0.7589 11.00000 0.05 0.23 Q5 1 0.4651 0.3803 1.5188 11.00000 0.05 0.23 Q6 1 0.2190 0.4973 0.2855 11.00000 0.05 0.21 Q7 1 0.2670 0.5019 0.5214 11.00000 0.05 0.20 Q8 1 0.3274 0.4441 0.4491 11.00000 0.05 0.20 ; _shelx_res_checksum 42242 _olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800' _olex2_submission_special_instructions 'No special instructions were received' 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 O2 O 0.46776(4) 0.4230(3) 1.0388(4) 0.0609(7) Uani 1 1 d . . . . . O1 O 0.49107(4) 0.6306(3) 1.2556(4) 0.0648(8) Uani 1 1 d . . . . . H1 H 0.503417 0.602744 1.168389 0.097 Uiso 1 1 calc R U . . . C1 C 0.46959(6) 0.5252(5) 1.2103(6) 0.0503(9) Uani 1 1 d . . . . . C4 C 0.40405(6) 0.5387(4) 1.1195(6) 0.0465(8) Uani 1 1 d . . . . . H4A H 0.413678 0.524235 0.973456 0.056 Uiso 1 1 calc R U . . . H4B H 0.402463 0.667072 1.150561 0.056 Uiso 1 1 calc R U . . . C6 C 0.35767(6) 0.5400(4) 0.8757(6) 0.0454(8) Uani 1 1 d . . . . . H6A H 0.356211 0.669125 0.901604 0.054 Uiso 1 1 calc R U . . . H6B H 0.367046 0.521895 0.729105 0.054 Uiso 1 1 calc R U . . . C7 C 0.32878(6) 0.4607(4) 0.8443(6) 0.0472(8) Uani 1 1 d . . . . . H7A H 0.319419 0.479591 0.990874 0.057 Uiso 1 1 calc R U . . . H7B H 0.330301 0.331394 0.820298 0.057 Uiso 1 1 calc R U . . . C5 C 0.37511(6) 0.4577(4) 1.0829(6) 0.0466(8) Uani 1 1 d . . . . . H5A H 0.376821 0.328866 1.055263 0.056 Uiso 1 1 calc R U . . . H5B H 0.365520 0.473579 1.228769 0.056 Uiso 1 1 calc R U . . . C9 C 0.28228(6) 0.4606(4) 0.6086(6) 0.0486(8) Uani 1 1 d . . . . . H9A H 0.273055 0.480212 0.755629 0.058 Uiso 1 1 calc R U . . . H9B H 0.283807 0.331175 0.585522 0.058 Uiso 1 1 calc R U . . . C8 C 0.31110(6) 0.5403(4) 0.6367(6) 0.0463(8) Uani 1 1 d . . . . . H8A H 0.309597 0.669734 0.660070 0.056 Uiso 1 1 calc R U . . . H8B H 0.320347 0.520751 0.489754 0.056 Uiso 1 1 calc R U . . . C3 C 0.42105(6) 0.4507(5) 1.3261(6) 0.0500(8) Uani 1 1 d . . . . . H3A H 0.410174 0.450344 1.466232 0.060 Uiso 1 1 calc R U . . . H3B H 0.424564 0.325898 1.284605 0.060 Uiso 1 1 calc R U . . . C11 C 0.23563(6) 0.4608(4) 0.3731(6) 0.0506(8) Uani 1 1 d . . . . . H11A H 0.226466 0.480707 0.520347 0.061 Uiso 1 1 calc R U . . . H11B H 0.237096 0.331315 0.350246 0.061 Uiso 1 1 calc R U . . . C10 C 0.26443(6) 0.5395(4) 0.4007(6) 0.0488(8) Uani 1 1 d . . . . . H10A H 0.262985 0.669082 0.423439 0.059 Uiso 1 1 calc R U . . . H10B H 0.273627 0.519486 0.253632 0.059 Uiso 1 1 calc R U . . . C12 C 0.21773(6) 0.5394(5) 0.1661(6) 0.0506(8) Uani 1 1 d . . . . . H12A H 0.216397 0.669033 0.188244 0.061 Uiso 1 1 calc R U . . . H12B H 0.226836 0.518673 0.018668 0.061 Uiso 1 1 calc R U . . . C13 C 0.18882(6) 0.4618(5) 0.1392(6) 0.0533(9) Uani 1 1 d . . . . . H13A H 0.190192 0.332122 0.117553 0.064 Uiso 1 1 calc R U . . . H13B H 0.179748 0.482599 0.286746 0.064 Uiso 1 1 calc R U . . . C14 C 0.17082(6) 0.5387(5) -0.0663(6) 0.0528(9) Uani 1 1 d . . . . . H14A H 0.169493 0.668421 -0.045010 0.063 Uiso 1 1 calc R U . . . H14B H 0.179851 0.517477 -0.213972 0.063 Uiso 1 1 calc R U . . . C2 C 0.44852(6) 0.5426(5) 1.3905(6) 0.0551(9) Uani 1 1 d . . . . . H2A H 0.445120 0.670116 1.416327 0.066 Uiso 1 1 calc R U . . . H2B H 0.456062 0.492676 1.540605 0.066 Uiso 1 1 calc R U . . . C15 C 0.14199(6) 0.4616(5) -0.0921(6) 0.0558(9) Uani 1 1 d . . . . . H15A H 0.133028 0.482101 0.056067 0.067 Uiso 1 1 calc R U . . . H15B H 0.143344 0.331924 -0.114132 0.067 Uiso 1 1 calc R U . . . C17 C 0.09509(7) 0.4612(5) -0.3195(6) 0.0607(10) Uani 1 1 d . . . . . H17A H 0.086319 0.481493 -0.170393 0.073 Uiso 1 1 calc R U . . . H17B H 0.096481 0.331593 -0.341605 0.073 Uiso 1 1 calc R U . . . C16 C 0.12384(6) 0.5384(5) -0.2959(6) 0.0563(9) Uani 1 1 d . . . . . H16A H 0.122509 0.668065 -0.274393 0.068 Uiso 1 1 calc R U . . . H16B H 0.132721 0.517282 -0.444333 0.068 Uiso 1 1 calc R U . . . C18 C 0.07648(7) 0.5374(5) -0.5223(7) 0.0636(10) Uani 1 1 d . . . . . H18A H 0.074927 0.666912 -0.499812 0.076 Uiso 1 1 calc R U . . . H18B H 0.085242 0.517725 -0.671563 0.076 Uiso 1 1 calc R U . . . C19 C 0.04795(7) 0.4584(6) -0.5444(7) 0.0788(13) Uani 1 1 d . . . . . H19A H 0.039247 0.477147 -0.394571 0.095 Uiso 1 1 calc R U . . . H19B H 0.049502 0.329000 -0.568119 0.095 Uiso 1 1 calc R U . . . C20 C 0.02930(9) 0.5353(7) -0.7452(9) 0.0977(15) Uani 1 1 d . . . . . H20A H 0.037389 0.514537 -0.895370 0.146 Uiso 1 1 calc R U . . . H20B H 0.027094 0.662860 -0.721428 0.146 Uiso 1 1 calc R U . . . H20C H 0.011570 0.477384 -0.746403 0.146 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 O2 0.0505(14) 0.0739(17) 0.0589(16) -0.0171(13) 0.0087(11) -0.0046(11) O1 0.0546(14) 0.0784(18) 0.0623(17) -0.0157(13) 0.0122(11) -0.0138(12) C1 0.0418(18) 0.060(2) 0.049(2) 0.0052(18) -0.0035(14) 0.0029(15) C4 0.0393(16) 0.050(2) 0.0501(19) -0.0006(15) 0.0017(14) -0.0020(13) C6 0.0413(16) 0.050(2) 0.0448(18) 0.0017(15) 0.0003(13) 0.0007(13) C7 0.0411(16) 0.053(2) 0.0470(19) 0.0001(15) 0.0006(13) -0.0001(14) C5 0.0418(17) 0.049(2) 0.0485(19) 0.0026(15) 0.0032(14) -0.0008(13) C9 0.0432(17) 0.055(2) 0.0472(19) 0.0001(15) -0.0032(14) 0.0019(14) C8 0.0416(17) 0.053(2) 0.0436(18) 0.0014(15) -0.0013(13) 0.0002(14) C3 0.0420(17) 0.061(2) 0.0471(19) 0.0038(16) 0.0063(14) -0.0006(14) C11 0.0452(18) 0.059(2) 0.0464(19) -0.0020(16) -0.0038(14) 0.0000(15) C10 0.0453(17) 0.054(2) 0.0471(19) 0.0037(15) -0.0016(14) -0.0010(14) C12 0.0457(18) 0.060(2) 0.0451(19) 0.0049(16) -0.0019(14) -0.0016(15) C13 0.0492(19) 0.065(2) 0.0452(19) 0.0012(16) -0.0038(15) -0.0004(15) C14 0.0476(18) 0.068(2) 0.0427(19) 0.0050(16) -0.0025(14) 0.0011(15) C2 0.0441(18) 0.074(3) 0.047(2) -0.0025(17) 0.0015(15) -0.0008(15) C15 0.0488(19) 0.073(3) 0.045(2) 0.0025(17) -0.0037(15) 0.0001(16) C17 0.052(2) 0.077(3) 0.052(2) 0.0013(18) -0.0043(16) 0.0022(17) C16 0.0473(19) 0.073(3) 0.047(2) 0.0038(17) -0.0031(15) 0.0010(16) C18 0.052(2) 0.082(3) 0.056(2) 0.0009(19) -0.0047(16) 0.0017(18) C19 0.056(2) 0.110(4) 0.069(3) 0.004(2) -0.0065(19) -0.003(2) C20 0.066(3) 0.142(4) 0.083(3) 0.006(3) -0.016(2) 0.004(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? O2 C1 O1 122.7(3) . . ? O2 C1 C2 124.6(3) . . ? O1 C1 C2 112.8(3) . . ? H4A C4 H4B 107.8 . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C3 C4 C5 112.7(3) . . ? H6A C6 H6B 107.7 . . ? C7 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C7 C6 C5 113.7(3) . . ? C5 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C6 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C6 C7 C8 114.5(3) . . ? H7A C7 H7B 107.6 . . ? C8 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C4 C5 H5A 108.7 . . ? C4 C5 H5B 108.7 . . ? C6 C5 C4 114.2(3) . . ? C6 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? H9A C9 H9B 107.6 . . ? C8 C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? C8 C9 C10 114.1(3) . . ? C10 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C7 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 C7 113.8(3) . . ? C9 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C4 C3 H3A 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C2 C3 C4 114.6(3) . . ? C2 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? H11A C11 H11B 107.6 . . ? C10 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C10 C11 C12 114.4(3) . . ? C12 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C9 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 C9 114.2(3) . . ? C11 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C13 C12 C11 114.5(3) . . ? C13 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C12 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C14 C13 C12 115.0(3) . . ? C14 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C13 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C15 C14 C13 114.9(3) . . ? C15 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? C1 C2 C3 115.4(3) . . ? C1 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C14 C15 H15A 108.5 . . ? C14 C15 H15B 108.5 . . ? C14 C15 C16 115.2(3) . . ? H15A C15 H15B 107.5 . . ? C16 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? H17A C17 H17B 107.4 . . ? C16 C17 H17A 108.4 . . ? C16 C17 H17B 108.4 . . ? C16 C17 C18 115.6(3) . . ? C18 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? C15 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 C15 114.8(3) . . ? C17 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.5 . . ? C17 C18 H18A 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C19 C18 C17 115.0(3) . . ? C19 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C18 C19 H19A 108.5 . . ? C18 C19 H19B 108.5 . . ? C18 C19 C20 115.0(4) . . ? H19A C19 H19B 107.5 . . ? C20 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? 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 O2 C1 1.221(4) . ? O1 H1 0.8200 . ? O1 C1 1.314(4) . ? C1 C2 1.481(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.528(4) . ? C4 C3 1.527(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.519(4) . ? C6 C5 1.522(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.522(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C8 1.516(4) . ? C9 C10 1.525(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C2 1.520(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C10 1.513(4) . ? C11 C12 1.522(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.514(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.514(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.509(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.511(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C16 1.505(4) . ? C17 C18 1.517(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 C19 1.500(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 C20 1.513(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O1 H1 O2 0.82 1.88 2.689(3) 171.2 3_667 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -11.4(5) . . . . ? O1 C1 C2 C3 169.5(3) . . . . ? C4 C3 C2 C1 -69.1(4) . . . . ? C6 C7 C8 C9 -179.7(3) . . . . ? C7 C6 C5 C4 -178.9(2) . . . . ? C5 C4 C3 C2 -172.4(3) . . . . ? C5 C6 C7 C8 -179.5(3) . . . . ? C8 C9 C10 C11 -179.7(3) . . . . ? C3 C4 C5 C6 -179.1(3) . . . . ? C11 C12 C13 C14 -179.9(3) . . . . ? C10 C9 C8 C7 -180.0(3) . . . . ? C10 C11 C12 C13 -179.6(3) . . . . ? C12 C11 C10 C9 179.9(3) . . . . ? C12 C13 C14 C15 -179.8(3) . . . . ? C13 C14 C15 C16 179.7(3) . . . . ? C14 C15 C16 C17 -179.7(3) . . . . ? C17 C18 C19 C20 179.5(3) . . . . ? C16 C17 C18 C19 179.6(3) . . . . ? C18 C17 C16 C15 179.6(3) . . . . ?