#------------------------------------------------------------------------------ #$Date: 2025-07-29 05:03:18 +0100 (Tue, 29 Jul 2025) $ #$Revision: 301391 $ #$URL: svn://www.crystallography.net/cod/cif/3/00/05/3000588.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_3000588 loop_ _publ_author_name 'Sasaki, Toshiyuki' 'Nakane, Takanori' 'Takimoto, Kazuyoshi' 'Ichiyanagi, Kouhei' 'Mori, Yuki' 'Baba, Seiki' 'Sakai, Naoki' 'Kurisu, Genji' 'Miyata, Mikiji' 'Uno, Takahiro' 'Itoh, Takahito' _publ_section_title ; Application of multiple small-wedge synchrotron crystallography for post-reaction structural characterization of a stimuli-responsive small-molecule crystal ; _journal_name_full 'Bulletin of the Chemical Society of Japan' _journal_paper_doi 10.1093/bulcsj/uoaf059 _journal_volume 98 _journal_year 2025 _chemical_formula_moiety 'C16 H16 O8' _chemical_formula_sum 'C16 H16 O8' _chemical_formula_weight 336.29 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2025-06-03 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 104.401(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.4689(3) _cell_length_b 7.6011(2) _cell_length_c 12.5302(4) _cell_measurement_reflns_used 2130 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.6420 _cell_measurement_theta_min 5.7620 _cell_volume 781.26(4) _computing_cell_refinement 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_data_reduction 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100.00 _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.992 _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 -100.00 -75.00 0.50 0.05 -- 0.00 0.00-180.00 50 2 \w -100.00 -75.00 0.50 0.05 -- 0.00 0.00-150.00 50 3 \w -100.00 -75.00 0.50 0.05 -- 0.00 0.00-120.00 50 4 \w -100.00 -75.00 0.50 0.05 -- 0.00 0.00 -60.00 50 5 \w 27.00 78.00 0.50 0.05 -- 111.23 -63.00 60.00 102 6 \w 27.00 54.00 0.50 0.05 -- 111.23 -50.00 60.00 54 7 \w 33.00 58.00 0.50 0.05 -- 111.23 -50.00 150.00 50 8 \w 61.00 114.00 0.50 0.05 -- 111.23-128.00 99.00 106 9 \w 44.00 116.00 0.50 0.05 -- 55.62-142.00 -71.00 144 10 \w 92.00 122.00 0.50 0.05 -- 111.23-142.00 -71.00 60 11 \w 72.00 100.00 0.50 0.05 -- 111.23-111.00-180.00 56 12 \w 111.00 136.00 0.50 0.05 -- 55.62 0.00-120.00 50 13 \w 118.00 159.00 0.50 0.05 -- 111.23 0.00 -90.00 82 14 \w 132.00 164.00 0.50 0.05 -- 111.23 0.00 -60.00 64 15 \w 115.00 178.00 0.50 0.05 -- 111.23 0.00 0.00 126 16 \w 106.00 138.00 0.50 0.05 -- 111.23 178.00-120.00 64 17 \w 68.00 95.00 0.50 0.05 -- 111.23 178.00-120.00 54 18 \w 86.00 147.00 0.50 0.05 -- 111.23 142.00 -15.00 122 19 \w -58.00 -32.00 0.50 0.05 -- 0.00 142.00 -15.00 52 20 \w -64.00 -38.00 0.50 0.05 -- 0.00 128.00 174.00 52 21 \w -7.00 24.00 0.50 0.05 -- -55.62 19.00 -60.00 62 22 \w -5.00 23.00 0.50 0.05 -- -55.62 19.00 -90.00 56 23 \w -50.00 -23.00 0.50 0.05 -- -106.00 63.00-150.00 54 24 \w -54.00 -25.00 0.50 0.05 -- -106.00 50.00 0.00 58 25 \w -52.00 -27.00 0.50 0.05 -- -106.00 50.00 60.00 50 26 \w -14.00 27.00 0.50 0.05 -- -55.62 19.00 30.00 82 27 \w -140.00-114.00 0.50 0.05 -- -55.62 -99.00-150.00 52 28 \w -139.00 -79.00 0.50 0.05 -- -55.62-142.00 -71.00 120 29 \w -123.00 -62.00 0.50 0.05 -- -106.00-142.00 -71.00 122 30 \w -147.00 -90.00 0.50 0.05 -- -55.62 -99.00 30.00 114 31 \w -104.00 -72.00 0.50 0.05 -- -55.62-128.00 99.00 64 32 \w -147.00-121.00 0.50 0.05 -- -55.62 -99.00-180.00 52 33 \w -118.00 -86.00 0.50 0.05 -- -55.62 -99.00-180.00 64 34 \w -67.00 -27.00 0.50 0.05 -- -106.00 111.00 120.00 80 35 \w -80.00 -43.00 0.50 0.05 -- -106.00 111.00 150.00 74 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3402 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.191 _diffrn_reflns_theta_min 5.710 _exptl_absorpt_coefficient_mu 0.993 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.80141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.430 _exptl_crystal_description plate _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.295 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef 0.0071(10) _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 1.159 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 142 _refine_ls_number_reflns 1415 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.159 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0352 _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^)+(0.0426P)^2^+0.1890P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.0907 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1365 _reflns_number_total 1415 _reflns_threshold_expression 'I > 2\s(I)' _journal_article_reference uoaf059 _cod_data_source_file Lab-Monomer1.cif _cod_data_source_block monomer1 _cod_depositor_comments ;Re-refinement of the structure. Hydrogen atoms were located from difference Fourier maps and refined, replacing the previous riding model (AFIX) treatment. Releasing structure 3000588 into public domain as published material. ; _cod_database_code 3000588 _journal_article_reference　 uoaf059 _journal_paper_doi　 　　10.1093/bulcsj/uoaf059　 _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 0.907 _shelx_estimated_absorpt_t_min 0.742 _olex2_refinement_description ; ; _shelx_res_file ; TITL exp_51_auto_a.res in P2(1)/n monomer1.res created by SHELXL-2018/3 at 18:45:29 on 03-Jun-2025 REM Old TITL exp_51_auto in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.108, Rweak 0.243, Alpha 0.018, Orientation as input REM Formula found by SHELXT: C8 O9 CELL 1.54184 8.4689 7.6011 12.5302 90 104.401 90 ZERR 2 0.0003 0.0002 0.0004 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H O UNIT 32 32 16 L.S. 10 PLAN 5 SIZE 0.1 0.2 0.32 TEMP -173.15 CONF BOND $H MORE -1 fmap 2 acta SHEL 99 0.83 REM REM REM WGHT 0.042600 0.189000 EXTI 0.007133 FVAR 1.06485 O10 3 0.304043 0.370304 0.707198 11.00000 0.02241 0.02705 = 0.01991 -0.00331 0.00612 -0.00194 O12 3 0.228772 0.587686 0.485731 11.00000 0.02351 0.02457 = 0.02200 -0.00090 0.00198 0.00233 O11 3 0.139951 0.354982 0.376507 11.00000 0.02371 0.02933 = 0.02183 -0.00182 0.00016 -0.00292 O9 3 0.535752 0.491001 0.683836 11.00000 0.02748 0.03215 = 0.02496 -0.00427 0.00467 -0.00962 C7 1 0.232819 0.418285 0.456253 11.00000 0.01986 0.02594 = 0.01951 0.00037 0.00763 -0.00216 C1 1 0.427604 0.166079 0.517370 11.00000 0.02135 0.02404 = 0.01802 0.00100 0.00532 -0.00500 C5 1 0.414086 0.406295 0.649964 11.00000 0.02126 0.01790 = 0.02070 0.00244 0.00418 0.00043 C4 1 0.361579 0.322295 0.537766 11.00000 0.02004 0.02360 = 0.01885 0.00000 0.00537 -0.00437 C3 1 0.611029 -0.079896 0.589671 11.00000 0.02387 0.02628 = 0.01717 0.00164 0.00305 -0.00055 C2 1 0.544378 0.075050 0.605273 11.00000 0.02549 0.02688 = 0.01588 -0.00020 0.00345 -0.00243 C6 1 0.338066 0.441007 0.818116 11.00000 0.03044 0.03095 = 0.02029 -0.00467 0.00626 0.00384 C8 1 0.107468 0.693524 0.411532 11.00000 0.02712 0.03065 = 0.02460 0.00269 0.00100 0.00531 H2 2 0.571778 0.126172 0.678322 11.00000 0.02450 H6A 2 0.444621 0.405968 0.860288 11.00000 0.03548 H3 2 0.679411 -0.138256 0.648407 11.00000 0.02379 H6B 2 0.330686 0.568832 0.814107 11.00000 0.03979 H8A 2 0.131834 0.698288 0.340937 11.00000 0.03550 H8B 2 0.002812 0.637321 0.401833 11.00000 0.03872 H6C 2 0.251072 0.393833 0.847406 11.00000 0.03573 H8C 2 0.113141 0.810784 0.446634 11.00000 0.04532 HKLF 4 REM exp_51_auto_a.res in P2(1)/n REM wR2 = 0.0907, GooF = S = 1.159, Restrained GooF = 1.159 for all data REM R1 = 0.0352 for 1365 Fo > 4sig(Fo) and 0.0366 for all 1415 data REM 142 parameters refined using 0 restraints END WGHT 0.0425 0.1891 REM Highest difference peak 0.295, deepest hole -0.189, 1-sigma level 0.040 Q1 1 0.3791 0.3669 0.5852 11.00000 0.05 0.29 Q2 1 0.3049 0.3702 0.5022 11.00000 0.05 0.24 Q3 1 0.4107 0.1224 0.4687 11.00000 0.05 0.23 Q4 1 0.4885 0.1107 0.5599 11.00000 0.05 0.22 Q5 1 0.3584 0.2249 0.5412 11.00000 0.05 0.18 ; _shelx_res_checksum 26738 _shelx_hkl_file ; 0 0 -1 0.19 0.10 0 0 -2 1598.43 5.34 0 0 -2 1556.62 8.64 0 0 -3 0.11 0.24 0 0 -4 400.10 6.92 0 0 -4 414.58 6.65 0 0 -4 413.15 6.83 0 0 -5 -0.07 0.26 0 0 -6 1164.89 14.28 0 0 -7 0.11 0.48 0 0 -8 24.09 2.58 0 0 -9 0.66 0.55 0 0 -10 494.03 13.96 0 0 -10 552.14 14.14 0 0 -11 0.42 0.41 0 0 -11 -0.27 0.64 0 0 -12 28.48 3.04 0 0 -12 17.45 2.91 0 0 -13 1.11 0.81 0 0 -13 0.64 0.89 0 0 -14 136.80 5.33 0 1 0 4.57 0.46 0 -1 -1 1925.18 6.64 0 1 -1 1922.92 6.88 0 -1 -2 570.88 5.24 0 1 -2 572.46 5.37 0 -1 -2 579.26 4.95 0 -1 -3 5.27 0.83 0 1 -3 7.62 0.78 0 1 -3 7.43 0.80 0 -1 -3 5.69 0.51 0 -1 -3 4.82 0.63 0 1 -4 72.39 2.36 0 1 4 64.27 1.83 0 1 -4 67.42 2.76 0 -1 -4 75.91 3.44 0 -1 -4 73.61 2.82 0 -1 -4 69.24 2.79 0 1 -4 71.72 3.11 0 1 -4 73.68 2.84 0 1 -5 1806.45 15.97 0 1 -5 1792.53 17.81 0 1 -6 1364.85 15.41 0 1 -6 1389.91 17.72 0 -1 -7 62.95 3.77 0 1 -7 68.09 3.87 0 -1 -8 8.53 1.57 0 1 -8 12.93 1.91 0 1 -9 9.14 1.81 0 -1 -9 12.41 2.10 0 1 -10 50.66 4.34 0 1 -10 46.14 4.29 0 -1 -10 49.29 4.44 0 1 -10 49.96 4.02 0 -1 -10 50.06 4.89 0 -1 -10 53.67 4.42 0 1 -10 48.96 4.42 0 -1 -10 51.58 4.12 0 -1 -11 223.22 10.78 0 1 -11 219.29 10.62 0 1 -11 213.24 9.69 0 -1 -12 64.00 4.60 0 1 -12 73.39 4.84 0 -1 -12 75.54 6.18 0 1 -12 71.79 5.48 0 1 -12 74.99 6.15 0 1 -13 16.43 2.65 0 1 -13 22.82 2.51 0 -1 -13 20.95 2.43 0 1 -14 129.35 5.00 0 -1 -14 127.59 4.99 0 2 0 1960.45 13.29 0 2 -1 1906.72 13.19 0 -2 -1 1894.25 15.49 0 2 -2 726.51 6.08 0 -2 2 712.62 5.90 0 2 -2 704.92 7.94 0 2 2 708.93 8.15 0 2 2 696.65 5.86 0 -2 -2 701.31 9.13 0 -2 -2 695.67 10.13 0 2 -2 734.68 8.41 0 -2 -3 289.73 6.49 0 2 -3 307.11 5.06 0 2 -3 289.18 6.71 0 -2 3 290.18 4.67 0 -2 -3 285.98 4.75 0 2 -3 287.32 5.85 0 -2 -3 276.31 7.07 0 2 -3 289.27 5.35 0 2 4 53.80 2.45 0 2 -4 62.42 3.20 0 -2 4 58.95 2.58 0 2 -4 64.92 2.58 0 -2 -4 56.42 2.44 0 2 -4 60.17 2.52 0 -2 -4 59.43 2.62 0 -2 -4 57.61 3.45 0 2 -4 58.80 2.64 0 2 -5 10.65 1.24 0 -2 -5 11.39 1.30 0 -2 -5 9.16 1.55 0 2 -6 452.87 9.10 0 2 -6 452.93 10.93 0 -2 -6 465.25 9.18 0 2 -7 474.16 12.29 0 -2 -7 464.10 10.31 0 -2 -8 203.40 7.51 0 2 -8 184.04 8.40 0 2 -8 210.11 7.57 0 -2 -9 238.47 8.66 0 2 -9 273.21 9.21 0 -2 -10 59.34 4.53 0 2 -10 55.11 5.02 0 2 -10 60.69 4.44 0 2 -11 17.97 2.83 0 2 -11 17.46 2.83 0 2 -11 18.80 2.43 0 -2 -11 16.61 2.23 0 2 -12 38.25 4.22 0 2 -12 36.91 3.96 0 2 -12 37.85 3.27 0 -2 -12 40.29 3.44 0 -2 -13 15.45 1.91 0 2 -13 17.57 2.00 0 2 -13 19.02 2.55 0 2 -13 21.51 2.84 0 2 -14 48.56 2.71 0 -2 -14 47.16 2.67 0 -3 0 6.25 1.09 0 -3 1 659.12 10.09 0 3 -1 655.44 8.39 0 -3 2 42.64 2.55 0 3 -2 43.96 2.40 0 -3 -2 46.55 3.22 0 -3 3 204.40 5.43 0 -3 -3 204.90 7.13 0 -3 -3 200.53 6.37 0 3 -3 223.80 5.89 0 -3 -4 540.28 11.28 0 3 -4 532.45 10.34 0 -3 -5 520.67 12.92 0 3 -5 539.96 11.64 0 -3 -6 2.53 1.03 0 3 -7 95.30 5.98 0 -3 -7 101.17 6.41 0 3 -8 1.30 0.74 0 3 -9 122.22 7.58 0 3 -9 128.88 7.28 0 3 -10 125.88 7.42 0 3 -10 132.15 7.90 0 3 -10 123.18 7.62 0 3 -11 86.33 6.38 0 3 -11 83.75 5.98 0 3 -11 92.72 6.37 0 3 -12 5.31 1.50 0 3 -12 3.00 1.16 0 3 -13 31.58 3.27 0 3 -14 19.18 2.00 0 4 0 3377.82 21.64 0 4 -1 138.22 4.58 0 -4 -1 137.99 6.49 0 -4 -2 293.92 9.70 0 -4 -2 288.86 8.36 0 4 -2 289.05 7.05 0 -4 -3 75.85 5.17 0 -4 -3 75.36 4.53 0 4 -3 85.60 4.25 0 4 -4 2.80 0.92 0 -4 -4 2.27 0.84 0 -4 -5 381.58 12.49 0 4 -5 399.31 11.13 0 -4 -6 4.06 1.50 0 4 -6 8.35 1.87 0 4 -7 84.12 5.98 0 -4 -7 78.60 6.15 0 4 -7 78.06 4.94 0 4 -8 279.36 10.36 0 4 -8 257.36 10.64 0 4 -9 13.44 2.60 0 4 -9 14.88 2.41 0 4 -10 8.45 1.80 0 4 -10 11.30 2.28 0 4 -11 2.69 1.03 0 4 -11 1.30 0.73 0 4 -11 1.66 0.77 0 4 -12 94.14 5.87 0 4 -12 89.58 5.30 0 4 -13 60.93 3.92 0 -5 0 4.32 1.42 0 -5 -1 5.06 1.52 0 5 -2 10.92 1.57 0 -5 -2 1.33 0.75 0 5 -3 363.65 9.99 0 -5 -3 373.50 13.17 0 -5 -4 1.51 0.74 0 5 -4 3.85 1.15 0 -5 -5 411.75 14.54 0 5 -5 406.82 12.31 0 -5 -6 819.10 20.97 0 5 -6 820.47 18.67 0 5 -7 286.53 11.60 0 -5 -7 265.71 12.01 0 5 -7 256.14 10.95 0 5 -7 263.07 10.90 0 -5 -7 250.80 10.22 0 5 -8 2.64 1.10 0 5 -8 3.20 1.18 0 -5 -8 3.05 1.09 0 5 -9 12.97 2.11 0 5 -10 17.55 2.74 0 5 -10 15.28 2.19 0 5 -11 186.45 8.12 0 5 -11 195.19 7.36 0 5 -11 199.07 8.16 0 5 -12 10.98 1.49 0 5 -12 11.76 1.80 0 -6 0 42.65 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-3 52.64 4.54 -8 -1 -3 54.95 4.68 -8 1 -3 67.83 5.22 -8 -1 -3 55.99 3.96 -8 1 -4 2.29 0.93 -8 1 -4 5.26 1.29 -8 -1 -4 3.25 1.14 -8 1 -5 9.95 1.67 -8 -1 -5 11.51 1.83 -8 1 -6 0.83 0.53 -8 -1 -6 0.10 0.54 8 -2 -11 3.40 0.73 8 2 -11 3.45 0.73 -8 -2 11 2.76 0.65 -8 2 11 2.16 0.57 8 -2 -10 0.82 0.40 8 2 -10 0.49 0.47 -8 -2 10 0.72 0.55 -8 2 10 1.24 0.50 -8 2 10 -0.12 1.38 8 -2 -9 1.10 0.50 8 2 -9 0.69 0.55 -8 -2 9 1.34 0.67 -8 2 9 1.10 0.51 -8 2 9 0.91 0.51 8 -2 -8 93.82 5.09 8 2 -8 97.19 5.04 -8 -2 8 90.77 5.01 -8 2 8 98.32 5.20 8 -2 -7 66.86 4.50 8 2 -7 67.96 4.39 -8 -2 7 64.83 4.42 -8 2 7 76.29 4.73 8 2 -6 67.56 5.53 -8 -2 6 54.93 4.11 -8 2 6 60.77 4.34 -8 -2 5 1.57 0.95 -8 2 5 0.46 0.67 -8 -2 4 4.61 1.39 -8 2 4 5.83 1.44 8 2 -4 6.43 1.65 8 2 -3 441.40 13.65 -8 -2 3 438.82 11.79 -8 2 3 434.05 11.56 -8 -2 2 175.75 7.44 -8 2 2 176.50 7.31 -8 2 2 182.71 7.92 -8 -2 1 89.88 5.28 -8 2 1 97.42 5.36 -8 -2 0 13.17 1.92 -8 2 0 13.10 1.94 -8 -2 -1 18.94 2.32 -8 2 -1 21.07 2.40 -8 -2 -1 16.15 2.46 -8 2 -2 33.59 4.07 -8 -2 -2 35.42 3.41 -8 2 -3 3.91 1.08 -8 -2 -3 4.61 1.42 -8 2 -3 4.64 1.48 -8 -2 -3 4.86 1.20 -8 2 -3 4.12 1.16 -8 2 -4 130.55 5.80 -8 -2 -4 122.52 5.85 -8 2 -4 140.56 6.75 -8 2 -5 138.61 5.66 -8 2 -5 125.83 4.93 -8 -2 -5 132.15 5.34 8 3 -10 42.18 2.70 -8 3 9 31.98 2.97 8 3 -8 25.07 2.97 -8 3 8 25.21 2.82 -8 3 7 1.04 0.86 8 3 -6 9.36 1.93 -8 3 6 9.32 1.97 8 3 -5 7.20 1.71 -8 3 5 6.13 1.52 8 3 -4 2.50 1.00 -8 -3 4 1.44 0.63 -8 3 4 2.57 0.95 8 3 -3 14.68 2.36 -8 -3 3 15.13 2.12 -8 3 3 17.51 2.48 -8 -3 2 243.17 8.97 -8 3 2 239.07 8.89 -8 -3 1 75.07 5.05 -8 3 0 110.69 7.34 -8 -3 0 130.56 6.56 -8 3 -1 165.11 8.81 -8 3 -2 95.77 6.13 -8 -3 -2 104.20 5.46 -8 3 -3 49.46 4.21 -8 3 -3 52.82 4.11 -8 3 -4 43.36 3.54 -8 3 -4 45.16 3.25 -8 3 -5 7.44 1.23 -8 4 9 1.00 0.44 8 4 -8 27.64 2.84 -8 4 8 28.00 2.77 -8 4 7 442.75 11.49 8 4 -6 0.35 0.77 -8 4 6 1.28 0.85 8 4 -5 489.95 13.35 -8 4 5 487.89 12.72 8 4 -4 3.08 1.03 -8 4 4 1.15 0.91 8 4 -3 6.67 1.48 -8 -4 3 7.60 1.35 -8 4 3 5.86 1.47 -8 4 2 17.37 2.56 -8 -4 2 13.88 1.99 -8 4 2 15.56 2.15 -8 4 1 5.34 1.42 -8 -4 1 3.84 1.14 -8 4 0 0.76 0.79 -8 -4 0 -0.14 0.49 -8 4 0 0.20 0.67 -8 4 -1 2.11 0.84 -8 4 -2 46.35 3.88 -8 4 -2 45.74 3.85 -8 4 -3 0.65 0.69 -8 4 -3 2.63 0.79 8 5 -8 6.64 1.12 -8 5 7 93.45 4.52 8 5 -6 9.75 1.63 -8 5 6 12.10 1.82 8 5 -5 41.36 3.36 -8 5 5 44.95 3.48 8 5 -4 36.39 3.12 -8 5 4 32.81 2.98 8 5 -3 27.54 2.57 -8 5 3 27.91 2.86 -8 5 3 25.20 2.61 -8 5 2 8.72 1.62 -8 5 2 7.34 1.25 -8 5 1 8.06 1.53 -8 5 0 9.87 1.48 -8 5 0 9.46 1.69 -8 5 -1 5.23 1.03 -8 5 -1 4.91 1.24 9 0 -10 0.09 0.39 -9 0 10 -0.09 0.40 9 0 -9 10.05 1.54 -9 0 9 10.94 1.58 9 0 -8 0.84 0.62 -9 0 8 -0.12 0.54 9 0 -7 3.96 1.18 -9 0 7 3.23 1.05 -9 0 6 -0.14 0.62 -9 0 5 122.05 6.02 -9 0 4 0.45 0.80 -9 0 3 79.86 4.91 -9 0 2 0.43 0.60 -9 0 1 24.40 2.66 -9 0 0 0.52 0.67 -9 0 -1 735.19 16.17 -9 0 -1 756.83 13.71 -9 0 -2 0.30 0.86 -9 0 -2 0.98 0.43 -9 0 -3 125.91 5.61 -9 0 -4 0.46 0.44 9 -1 -10 8.70 1.23 9 1 -10 8.09 1.22 -9 1 10 9.84 1.32 9 -1 -9 1.58 0.69 9 1 -9 0.67 0.55 -9 -1 9 0.50 0.57 -9 1 9 0.90 0.53 -9 1 9 2.71 0.78 9 -1 -8 93.15 4.67 9 1 -8 90.67 4.52 -9 -1 8 89.01 4.57 -9 1 8 93.11 4.69 9 -1 -7 8.10 1.50 9 1 -7 5.19 1.23 -9 -1 7 6.51 1.37 -9 1 7 6.47 1.36 -9 -1 6 0.14 0.57 -9 1 6 0.13 0.49 -9 -1 5 92.61 5.15 -9 1 5 89.96 5.07 -9 -1 4 239.53 8.28 -9 1 4 245.92 8.36 -9 -1 3 8.92 1.71 -9 1 3 9.60 1.76 -9 -1 2 46.42 3.64 -9 1 2 48.64 3.67 -9 -1 1 16.57 2.17 -9 1 1 16.36 2.10 -9 -1 0 151.21 6.15 -9 1 0 147.93 6.02 -9 -1 0 159.38 6.75 -9 1 -1 28.06 3.30 -9 -1 -1 33.31 2.94 -9 1 -2 157.67 6.63 -9 -1 -2 163.35 6.90 -9 1 -2 164.08 7.08 -9 -1 -2 164.18 5.84 -9 1 -3 62.09 3.75 -9 -1 -3 69.74 4.08 -9 1 -3 66.44 3.75 9 -2 -9 1.13 0.40 9 2 -9 1.03 0.42 -9 2 9 1.04 0.52 9 -2 -8 16.46 1.77 9 2 -8 13.90 1.60 -9 -2 8 13.98 1.63 -9 2 8 15.70 1.74 -9 2 8 14.05 1.97 9 -2 -7 7.65 1.30 9 2 -7 9.11 1.39 -9 -2 7 7.63 1.30 -9 2 7 9.64 1.42 -9 2 7 8.59 1.67 9 -2 -6 5.37 1.11 -9 -2 6 4.20 1.03 -9 2 6 4.93 1.08 -9 2 6 6.38 1.44 -9 -2 5 8.56 1.40 -9 2 5 8.62 1.45 -9 -2 5 10.21 1.55 -9 2 5 10.33 1.93 -9 -2 4 0.48 0.53 -9 2 4 0.83 0.61 -9 -2 4 1.85 0.75 -9 2 4 1.50 0.66 -9 -2 3 0.24 0.58 -9 2 3 0.82 0.69 -9 -2 3 0.56 0.61 -9 2 3 2.10 0.75 -9 -2 2 337.34 8.93 -9 2 2 355.95 9.04 -9 -2 2 359.91 10.20 -9 -2 1 23.47 2.32 -9 2 1 19.53 2.11 -9 -2 1 24.88 2.70 -9 -2 0 24.08 2.27 -9 2 0 26.48 2.34 -9 2 -1 26.24 2.55 -9 -2 -1 22.36 2.46 -9 2 -1 26.10 3.11 -9 -2 -1 23.13 2.34 -9 2 -1 23.46 2.66 -9 2 -2 26.76 2.38 -9 -2 -2 26.38 2.44 -9 2 -2 32.75 3.04 -9 -2 -2 28.48 2.39 -9 2 -3 25.34 2.29 -9 3 8 101.39 4.68 -9 3 7 -0.12 0.56 -9 3 6 4.35 1.21 -9 3 5 4.19 1.12 -9 -3 4 2.18 0.66 -9 3 4 1.32 0.66 -9 -3 3 13.18 1.75 -9 3 3 16.21 2.00 -9 3 2 1.44 1.03 -9 -3 2 0.35 0.59 -9 3 1 77.69 5.27 -9 -3 1 75.42 4.24 -9 3 0 9.77 1.90 -9 -3 0 8.32 1.43 -9 3 0 9.72 1.78 -9 3 -1 1.53 0.84 -9 -3 -1 0.97 0.54 -9 3 -1 1.95 0.70 -9 3 -2 4.92 1.19 -9 4 7 31.60 2.44 -9 4 6 69.37 3.80 -9 4 5 14.67 1.80 -9 4 4 6.78 1.24 -9 4 3 15.48 1.70 -9 4 3 14.84 2.10 -9 4 2 29.25 2.65 -9 4 2 27.67 2.76 -9 4 1 13.25 1.76 -9 4 1 10.62 1.72 -9 4 0 58.94 3.57 10 0 -7 -0.08 0.45 10 0 -6 109.82 4.41 -10 0 6 106.68 4.29 -10 0 5 0.09 0.53 -10 0 4 61.15 3.42 -10 0 4 64.93 3.49 -10 0 3 0.18 0.42 -10 0 2 32.34 2.40 -10 0 2 35.23 2.68 -10 0 1 0.75 0.42 -10 0 1 0.24 0.35 -10 0 1 0.53 0.49 -10 0 0 25.05 2.32 10 -1 -7 2.68 0.66 10 1 -7 0.84 0.50 -10 1 7 1.89 0.64 10 -1 -6 21.28 1.92 10 1 -6 27.59 2.14 -10 1 6 22.50 2.13 -10 -1 5 81.03 3.74 -10 1 5 84.02 3.76 -10 1 5 87.97 4.15 -10 -1 4 13.42 1.56 -10 1 4 13.92 1.56 -10 -1 4 11.09 1.59 -10 1 4 12.00 1.52 -10 -1 3 257.34 6.58 -10 1 3 257.90 6.59 -10 -1 3 244.50 6.93 -10 -1 2 56.34 3.05 -10 1 2 52.76 2.94 -10 -1 2 52.93 3.20 -10 1 1 1.28 0.66 -10 2 3 225.31 7.64 -10 2 2 44.04 3.35 0 0 0 0.00 0.00 TITL exp_51_auto in P2(1)/n REM P2(1)/n (#14 in standard setting) CELL 1.54184 8.468939 7.601073 12.530250 90.0000 104.4006 90.0000 ZERR 2.00 0.000263 0.000240 0.000370 0.0000 0.0032 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H O UNIT 32.00 36.00 16.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 64547 _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 ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 O10 O 0.30404(11) 0.37030(13) 0.70720(7) 0.0230(3) Uani 1 1 d . . . . . O12 O 0.22877(12) 0.58769(13) 0.48573(8) 0.0240(3) Uani 1 1 d . . . . . O11 O 0.13995(11) 0.35498(14) 0.37651(8) 0.0259(3) Uani 1 1 d . . . . . O9 O 0.53575(12) 0.49100(14) 0.68384(8) 0.0285(3) Uani 1 1 d . . . . . C7 C 0.23282(16) 0.4183(2) 0.45625(11) 0.0213(3) Uani 1 1 d . . . . . C1 C 0.42760(16) 0.16608(19) 0.51737(11) 0.0211(3) Uani 1 1 d . . . . . C5 C 0.41409(16) 0.40630(18) 0.64996(11) 0.0201(3) Uani 1 1 d . . . . . C4 C 0.36158(16) 0.32230(19) 0.53777(11) 0.0207(3) Uani 1 1 d . . . . . C3 C 0.61103(17) -0.0799(2) 0.58967(11) 0.0228(3) Uani 1 1 d . . . . . C2 C 0.54438(17) 0.0751(2) 0.60527(11) 0.0230(3) Uani 1 1 d . . . . . C6 C 0.33807(19) 0.4410(2) 0.81812(12) 0.0272(4) Uani 1 1 d . . . . . C8 C 0.10747(19) 0.6935(2) 0.41153(12) 0.0284(4) Uani 1 1 d . . . . . H2 H 0.5718(19) 0.126(2) 0.6783(13) 0.024(4) Uiso 1 1 d . . . . . H6A H 0.445(2) 0.406(3) 0.8603(15) 0.035(5) Uiso 1 1 d . . . . . H3 H 0.6794(19) -0.138(2) 0.6484(13) 0.024(4) Uiso 1 1 d . . . . . H6B H 0.331(2) 0.569(3) 0.8141(15) 0.040(5) Uiso 1 1 d . . . . . H8A H 0.132(2) 0.698(3) 0.3409(15) 0.036(5) Uiso 1 1 d . . . . . H8B H 0.003(2) 0.637(3) 0.4018(14) 0.039(5) Uiso 1 1 d . . . . . H6C H 0.251(2) 0.394(2) 0.8474(15) 0.036(5) Uiso 1 1 d . . . . . H8C H 0.113(2) 0.811(3) 0.4466(16) 0.045(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 O10 0.0224(5) 0.0271(6) 0.0199(5) -0.0033(4) 0.0061(4) -0.0019(4) O12 0.0235(5) 0.0246(6) 0.0220(5) -0.0009(4) 0.0020(4) 0.0023(4) O11 0.0237(5) 0.0293(6) 0.0218(5) -0.0018(4) 0.0002(4) -0.0029(4) O9 0.0275(5) 0.0322(6) 0.0250(5) -0.0043(4) 0.0047(4) -0.0096(5) C7 0.0199(6) 0.0259(8) 0.0195(7) 0.0004(5) 0.0076(5) -0.0022(6) C1 0.0213(7) 0.0240(7) 0.0180(6) 0.0010(6) 0.0053(5) -0.0050(6) C5 0.0213(6) 0.0179(7) 0.0207(7) 0.0024(5) 0.0042(5) 0.0004(5) C4 0.0200(6) 0.0236(7) 0.0189(7) 0.0000(5) 0.0054(5) -0.0044(5) C3 0.0239(7) 0.0263(8) 0.0172(7) 0.0016(6) 0.0031(5) -0.0006(6) C2 0.0255(7) 0.0269(8) 0.0159(6) -0.0002(6) 0.0035(5) -0.0024(6) C6 0.0304(8) 0.0309(9) 0.0203(7) -0.0047(6) 0.0063(6) 0.0038(7) C8 0.0271(8) 0.0306(9) 0.0246(8) 0.0027(6) 0.0010(6) 0.0053(7) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C5 O10 C6 116.04(11) . . C7 O12 C8 114.79(11) . . O12 C7 C4 110.26(11) . . O11 C7 O12 123.65(13) . . O11 C7 C4 126.05(14) . . C4 C1 C3 123.80(13) . 3_656 C4 C1 C2 120.27(12) . . C3 C1 C2 115.93(13) 3_656 . O10 C5 C4 109.28(11) . . O9 C5 O10 124.86(12) . . O9 C5 C4 125.85(12) . . C7 C4 C5 115.39(12) . . C1 C4 C7 124.30(12) . . C1 C4 C5 120.28(12) . . C1 C3 H3 117.9(10) 3_656 . C2 C3 C1 121.56(13) . 3_656 C2 C3 H3 120.4(10) . . C1 C2 H2 118.8(10) . . C3 C2 C1 122.50(13) . . C3 C2 H2 118.7(10) . . O10 C6 H6A 111.0(11) . . O10 C6 H6B 109.0(11) . . O10 C6 H6C 103.7(11) . . H6A C6 H6B 110.1(16) . . H6A C6 H6C 112.7(15) . . H6B C6 H6C 110.1(16) . . O12 C8 H8A 109.5(11) . . O12 C8 H8B 108.6(11) . . O12 C8 H8C 105.5(11) . . H8A C8 H8B 107.6(15) . . H8A C8 H8C 112.2(16) . . H8B C8 H8C 113.4(16) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O10 C5 1.3380(16) . O10 C6 1.4506(16) . O12 C7 1.3423(18) . O12 C8 1.4463(17) . O11 C7 1.2073(17) . O9 C5 1.1995(17) . C7 C4 1.4868(19) . C1 C4 1.363(2) . C1 C3 1.4549(19) 3_656 C1 C2 1.4588(19) . C5 C4 1.5069(18) . C3 C2 1.341(2) . C3 H3 0.928(16) . C2 H2 0.968(17) . C6 H6A 0.963(19) . C6 H6B 0.97(2) . C6 H6C 0.97(2) . C8 H8A 0.958(19) . C8 H8B 0.96(2) . C8 H8C 0.99(2) . 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 O10 C5 C4 C7 79.01(14) . . . . O10 C5 C4 C1 -99.09(15) . . . . O12 C7 C4 C1 -160.73(12) . . . . O12 C7 C4 C5 21.27(16) . . . . O11 C7 C4 C1 21.7(2) . . . . O11 C7 C4 C5 -156.33(13) . . . . O9 C5 C4 C7 -101.60(17) . . . . O9 C5 C4 C1 80.31(19) . . . . C1 C3 C2 C1 1.0(2) 3_656 . . . C4 C1 C2 C3 179.11(13) . . . . C3 C1 C4 C7 4.8(2) 3_656 . . . C3 C1 C4 C5 -177.29(12) 3_656 . . . C3 C1 C2 C3 -0.9(2) 3_656 . . . C2 C1 C4 C7 -175.23(12) . . . . C2 C1 C4 C5 2.68(19) . . . . C6 O10 C5 O9 0.0(2) . . . . C6 O10 C5 C4 179.44(12) . . . . C8 O12 C7 O11 -2.47(19) . . . . C8 O12 C7 C4 179.85(11) . . . . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code _cod_related_entry_description 1 XRDa 00329 DOI:10.51093/xrd-00329