#------------------------------------------------------------------------------ #$Date: 2024-06-15 01:11:51 +0300 (Sat, 15 Jun 2024) $ #$Revision: 292401 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571893.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_1571893 loop_ _publ_author_name 'Nicolai, Stefano' 'Waser, J\'er\^ome' _publ_section_title ; Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02767A _journal_year 2024 _chemical_formula_moiety 'C21 H22 O2' _chemical_formula_sum 'C21 H22 O2' _chemical_formula_weight 306.38 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2024-02-20 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2024-02-20 deposited with the CCDC. 2024-06-14 downloaded from the CCDC. ; _cell_angle_alpha 67.728(3) _cell_angle_beta 74.021(2) _cell_angle_gamma 82.9324(19) _cell_formula_units_Z 2 _cell_length_a 8.11476(18) _cell_length_b 10.4720(2) _cell_length_c 10.7595(4) _cell_measurement_reflns_used 11017 _cell_measurement_temperature 140.00(10) _cell_measurement_theta_max 75.3950 _cell_measurement_theta_min 4.5480 _cell_volume 813.23(4) _computing_cell_refinement 'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))' _computing_data_reduction 'CrysAlisPro 1.171.43.105a (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 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 140.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type 'HyPix-Arc 150' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.970 _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 -108.00 -34.00 0.50 0.20 -- -76.25 132.00 74.01 148 2 \w -108.00 -34.00 0.50 0.20 -- -76.25 132.00 74.01 148 3 \w -108.00 -33.00 0.50 0.20 -- -70.95 0.00 -60.00 150 4 \w -108.00 -33.00 0.50 0.20 -- -70.95 0.00 -60.00 150 5 \w -112.00 -80.00 0.50 0.20 -- -76.25 -76.00 -62.27 64 6 \w -118.00 -86.00 0.50 0.20 -- -76.25 -60.00 7.60 64 7 \w -74.00 -43.00 0.50 0.20 -- -36.00 -69.00 132.42 62 8 \w -115.00 -84.00 0.50 0.20 -- -76.25 -67.00 149.39 62 9 \w -119.00 -86.00 0.50 0.20 -- -76.25 -56.00 139.53 66 10 \w -112.00 -79.00 0.50 0.20 -- -68.00 -52.00 104.70 66 11 \w -118.00 -85.00 0.50 0.20 -- -72.00 -41.00 65.33 66 12 \w -123.00 -86.00 0.50 0.20 -- -76.25 -36.00 71.26 74 13 \w -114.00 -81.00 0.50 0.20 -- -68.00 -41.00 27.86 66 14 \w -74.00 -43.00 0.50 0.20 -- -36.00 -69.00-154.64 62 15 \w -121.00 -87.00 0.50 0.20 -- -76.25 -50.00-175.47 68 16 \w -112.00 -79.00 0.50 0.20 -- -76.25 -90.00 -16.61 66 17 \w 46.00 77.00 0.50 0.20 -- 40.00 72.00-136.17 62 18 \w 40.00 72.00 0.50 0.20 -- 36.00 76.00 54.40 64 19 \w 45.00 77.00 0.50 0.20 -- 40.00 74.00 113.73 64 20 \w 51.00 84.00 0.50 0.20 -- 40.00 53.00 29.85 66 21 \w 47.00 74.00 0.50 0.20 -- 79.75 2.00 -37.28 54 22 \w 62.00 94.00 0.50 0.20 -- 52.00 58.00 -51.26 64 23 \w 69.00 101.00 0.50 0.20 -- 60.00 62.00-132.95 64 24 \w 62.00 95.00 0.50 0.20 -- 52.00 57.00 -93.10 66 25 \w 91.00 116.00 0.50 0.20 -- 79.75 49.00 -36.70 50 26 \w 94.00 125.00 0.50 0.20 -- 79.75 35.00 -51.64 62 27 \w 77.00 105.00 0.50 0.20 -- 79.75 26.00 -78.77 56 28 \w 73.00 106.00 0.50 0.20 -- 79.75 25.00 -44.42 66 29 \w 100.00 126.00 0.50 0.20 -- 79.75 32.00 -7.85 52 30 \w 45.00 110.00 0.50 0.20 -- 79.75 3.00-131.14 130 31 \w 79.00 110.00 0.50 0.20 -- 79.75 3.00-101.06 62 32 \w 97.00 124.00 0.50 0.20 -- 79.75 46.00 25.36 54 33 \w 94.00 121.00 0.50 0.20 -- 79.75 6.00 152.15 54 34 \w 58.00 88.00 0.50 0.20 -- 79.75 6.00 152.15 60 35 \w 35.00 103.00 0.50 0.20 -- 76.40-125.00 90.00 136 36 \w 35.00 103.00 0.50 0.20 -- 76.40-125.00 150.00 136 37 \w 35.00 103.00 0.50 0.20 -- 76.40-125.00 120.00 136 38 \w 35.00 103.00 0.50 0.20 -- 76.40-125.00 90.00 136 39 \w 35.00 103.00 0.50 0.20 -- 76.40-125.00 -30.00 136 40 \w 35.00 103.00 0.50 0.20 -- 76.40-125.00 -90.00 136 41 \w 49.00 103.00 0.50 0.20 -- 76.40-125.00-150.00 108 42 \w 40.00 105.00 0.50 0.20 -- 79.75-123.00-137.96 130 43 \w 38.00 84.00 0.50 0.20 -- 75.71 -95.00-150.00 92 44 \w 48.00 99.00 0.50 0.20 -- 79.75-113.00 -76.36 102 45 \w 39.00 85.00 0.50 0.20 -- 76.40 -95.00 -30.00 92 46 \w 39.00 85.00 0.50 0.20 -- 76.40 -95.00-120.00 92 47 \w 41.00 105.00 0.50 0.20 -- 79.75-122.00 36.50 128 48 \w 46.00 91.00 0.50 0.20 -- 79.75-100.00 71.83 90 49 \w 39.00 85.00 0.50 0.20 -- 76.40 -95.00 90.00 92 50 \w 39.00 85.00 0.50 0.20 -- 76.40 -95.00 150.00 92 51 \w 39.00 85.00 0.50 0.20 -- 76.40 -95.00 120.00 92 52 \w 38.00 84.00 0.50 0.20 -- 75.71 -95.00 30.00 92 53 \w 39.00 85.00 0.50 0.20 -- 76.40 -95.00 0.00 92 54 \w 26.00 72.00 0.50 0.20 -- 63.71 -95.00 -30.00 92 55 \w 38.00 84.00 0.50 0.20 -- 75.71 -95.00 -60.00 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix-Arc 150' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0170050000 _diffrn_orient_matrix_UB_12 -0.0087649000 _diffrn_orient_matrix_UB_13 0.1421478000 _diffrn_orient_matrix_UB_21 0.0900846000 _diffrn_orient_matrix_UB_22 0.1399457000 _diffrn_orient_matrix_UB_23 -0.0691481000 _diffrn_orient_matrix_UB_31 -0.1749574000 _diffrn_orient_matrix_UB_32 0.0749796000 _diffrn_orient_matrix_UB_33 0.0231179000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_unetI/netI 0.0139 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 17602 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.563 _diffrn_reflns_theta_min 4.564 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.637 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear pale colourless' _exptl_crystal_density_diffrn 1.251 _exptl_crystal_description prism _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.213 _exptl_crystal_size_mid 0.187 _exptl_crystal_size_min 0.134 _refine_diff_density_max 0.288 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.0025(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 3274 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0571P)^2^+0.2306P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1107 _refine_ls_wR_factor_ref 0.1140 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2901 _reflns_number_total 3274 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02767a2.cif _cod_data_source_block ste-24-1037 _cod_database_code 1571893 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula 'C21 H22 O2' _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 0.922 _shelx_estimated_absorpt_t_min 0.880 _olex2_refinement_description ; ; _shelx_res_file ; TITL STE-24-1037 in P-1 ste-24-1037.res created by SHELXL-2019/3 at 13:32:03 on 20-Feb-2024 CELL 1.54184 8.11476 10.472 10.7595 67.728 74.021 82.9324 ZERR 2 0.00018 0.0002 0.0004 0.003 0.002 0.0019 LATT 1 SFAC C H O UNIT 42 44 4 L.S. 10 PLAN 10 SIZE 0.213 0.187 0.134 TEMP -133 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.057100 0.230600 EXTI 0.002540 FVAR 8.54601 O1 3 0.375082 0.030016 0.357081 11.00000 0.04814 0.03304 = 0.05447 -0.02016 -0.00137 -0.00292 O2 3 -0.137833 0.399611 0.659782 11.00000 0.04213 0.03593 = 0.05233 -0.01753 -0.00583 0.00132 C1 1 0.358607 0.142644 0.369183 11.00000 0.03145 0.02911 = 0.03735 -0.01040 -0.01147 0.00162 C2 1 0.219628 0.165940 0.486357 11.00000 0.02974 0.02385 = 0.03115 -0.00584 -0.00880 -0.00129 C3 1 0.150144 0.033137 0.610303 11.00000 0.03995 0.02433 = 0.03374 -0.00388 -0.01191 0.00043 H3A 2 0.236618 -0.040902 0.617513 11.00000 0.03678 H3B 2 0.040340 -0.002425 0.611900 11.00000 0.03923 C4 1 0.148712 0.107956 0.710141 11.00000 0.03911 0.03128 = 0.03080 -0.00524 -0.01364 0.00181 H4 2 0.192233 0.051091 0.791041 11.00000 0.03489 C5 1 -0.019078 0.178201 0.762118 11.00000 0.03882 0.03555 = 0.03209 -0.00889 -0.00763 -0.00351 H5 2 0.002342 0.228724 0.823558 11.00000 0.03775 C6 1 -0.087707 0.289653 0.647624 11.00000 0.02569 0.02952 = 0.03688 -0.00773 -0.00267 -0.00443 C7 1 -0.099885 0.257828 0.524372 11.00000 0.02798 0.03065 = 0.03527 -0.00535 -0.00905 -0.00281 H7 2 -0.145380 0.162986 0.561144 11.00000 0.03880 C8 1 0.077122 0.257884 0.424189 11.00000 0.02911 0.02552 = 0.03053 -0.00414 -0.00941 -0.00244 H8A 2 0.113395 0.355402 0.377675 11.00000 0.03773 H8B 2 0.058321 0.228419 0.352607 11.00000 0.03745 C9 1 0.276085 0.211794 0.590657 11.00000 0.02995 0.03288 = 0.03616 -0.01136 -0.01182 0.00163 H9A 2 0.255292 0.311617 0.581738 11.00000 0.03849 H9B 2 0.394136 0.181861 0.593908 11.00000 0.03651 C10 1 -0.160641 0.075233 0.855088 11.00000 0.05091 0.04214 = 0.03544 -0.00574 -0.00522 -0.01142 H10A 2 -0.197078 0.024892 0.798452 11.00000 0.05427 H10B 2 -0.269013 0.127150 0.891146 11.00000 0.05745 H10C 2 -0.115180 0.007018 0.934885 11.00000 0.06225 C11 1 -0.218621 0.358611 0.443482 11.00000 0.03157 0.04523 = 0.04502 -0.00815 -0.01441 0.00312 H11A 2 -0.175378 0.452206 0.404865 11.00000 0.05424 H11B 2 -0.335210 0.362698 0.500415 11.00000 0.05846 H11C 2 -0.228896 0.330942 0.367516 11.00000 0.05532 C12 1 0.472029 0.258182 0.265611 11.00000 0.02577 0.03218 = 0.03230 -0.00860 -0.01052 0.00250 C13 1 0.464864 0.385931 0.275106 11.00000 0.02637 0.03401 = 0.03036 -0.00935 -0.00878 -0.00031 H13 2 0.387888 0.409282 0.349301 11.00000 0.02852 C14 1 0.576393 0.492393 0.175026 11.00000 0.02591 0.03356 = 0.03094 -0.00666 -0.01213 0.00009 C15 1 0.573080 0.623158 0.185343 11.00000 0.03405 0.03791 = 0.03401 -0.01000 -0.00879 -0.00481 H15 2 0.488750 0.643337 0.259408 11.00000 0.03674 C16 1 0.684060 0.723296 0.088610 11.00000 0.04185 0.03763 = 0.04012 -0.00688 -0.01196 -0.00929 H16 2 0.678287 0.815951 0.095887 11.00000 0.04718 C17 1 0.803259 0.695811 -0.021917 11.00000 0.03810 0.04430 = 0.03625 -0.00091 -0.00854 -0.00850 H17 2 0.884789 0.769640 -0.092553 11.00000 0.05725 C18 1 0.808732 0.571205 -0.035187 11.00000 0.03472 0.04473 = 0.03163 -0.00380 -0.00437 0.00017 H18 2 0.891170 0.548197 -0.108573 11.00000 0.04514 C19 1 0.695386 0.465159 0.063306 11.00000 0.02926 0.03882 = 0.02961 -0.00572 -0.01044 0.00241 C20 1 0.697740 0.333612 0.054018 11.00000 0.03775 0.04184 = 0.03308 -0.01113 -0.00473 0.00663 H20 2 0.778560 0.318071 -0.024795 11.00000 0.05135 C21 1 0.590223 0.233184 0.151644 11.00000 0.03653 0.03534 = 0.03694 -0.01187 -0.01024 0.00599 H21 2 0.591438 0.140490 0.142357 11.00000 0.05463 HKLF 4 REM STE-24-1037 in P-1 REM wR2 = 0.1140, GooF = S = 1.070, Restrained GooF = 1.070 for all data REM R1 = 0.0409 for 2901 Fo > 4sig(Fo) and 0.0455 for all 3274 data REM 297 parameters refined using 0 restraints END WGHT 0.0570 0.2308 REM Highest difference peak 0.288, deepest hole -0.199, 1-sigma level 0.034 Q1 1 -0.0735 0.1181 0.7558 11.00000 0.05 0.29 Q2 1 0.1162 0.0580 0.6801 11.00000 0.05 0.24 Q3 1 0.7357 0.3844 0.0849 11.00000 0.05 0.23 Q4 1 0.1798 0.0986 0.5336 11.00000 0.05 0.23 Q5 1 0.2854 0.1609 0.4281 11.00000 0.05 0.23 Q6 1 0.4107 0.2030 0.3184 11.00000 0.05 0.21 Q7 1 0.0605 0.1447 0.7371 11.00000 0.05 0.21 Q8 1 -0.3160 0.1826 0.6886 11.00000 0.05 0.21 Q9 1 0.2533 0.1992 0.5219 11.00000 0.05 0.21 Q10 1 0.1484 0.2159 0.4624 11.00000 0.05 0.20 ; _shelx_res_checksum 88477 _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 - Detector area scaling - B-factor correction ; _oxdiff_exptl_absorpt_empirical_full_max 1.814 _oxdiff_exptl_absorpt_empirical_full_min 0.519 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 0.37508(14) 0.03002(10) 0.35708(11) 0.0461(3) Uani 1 1 d . . . . . O2 O -0.13783(13) 0.39961(10) 0.65978(11) 0.0444(3) Uani 1 1 d . . . . . C1 C 0.35861(17) 0.14264(13) 0.36918(14) 0.0327(3) Uani 1 1 d . . . . . C2 C 0.21963(16) 0.16594(12) 0.48636(13) 0.0292(3) Uani 1 1 d . . . . . C3 C 0.15014(19) 0.03314(13) 0.61030(14) 0.0342(3) Uani 1 1 d . . . . . H3A H 0.237(2) -0.0409(16) 0.6175(16) 0.037(4) Uiso 1 1 d . . . . . H3B H 0.040(2) -0.0024(16) 0.6119(16) 0.039(4) Uiso 1 1 d . . . . . C4 C 0.14871(18) 0.10796(13) 0.71014(14) 0.0347(3) Uani 1 1 d . . . . . H4 H 0.1922(19) 0.0511(16) 0.7910(16) 0.035(4) Uiso 1 1 d . . . . . C5 C -0.01908(18) 0.17820(14) 0.76212(14) 0.0365(3) Uani 1 1 d . . . . . H5 H 0.002(2) 0.2287(16) 0.8236(16) 0.038(4) Uiso 1 1 d . . . . . C6 C -0.08771(16) 0.28965(13) 0.64762(14) 0.0327(3) Uani 1 1 d . . . . . C7 C -0.09989(16) 0.25783(13) 0.52437(14) 0.0329(3) Uani 1 1 d . . . . . H7 H -0.145(2) 0.1630(17) 0.5611(16) 0.039(4) Uiso 1 1 d . . . . . C8 C 0.07712(16) 0.25788(12) 0.42419(13) 0.0296(3) Uani 1 1 d . . . . . H8A H 0.113(2) 0.3554(16) 0.3777(16) 0.038(4) Uiso 1 1 d . . . . . H8B H 0.058(2) 0.2284(16) 0.3526(17) 0.037(4) Uiso 1 1 d . . . . . C9 C 0.27608(17) 0.21179(14) 0.59066(14) 0.0328(3) Uani 1 1 d . . . . . H9A H 0.255(2) 0.3116(17) 0.5817(16) 0.038(4) Uiso 1 1 d . . . . . H9B H 0.394(2) 0.1819(15) 0.5939(16) 0.037(4) Uiso 1 1 d . . . . . C10 C -0.1606(2) 0.07523(17) 0.85509(16) 0.0456(4) Uani 1 1 d . . . . . H10A H -0.197(2) 0.0249(18) 0.7985(19) 0.054(5) Uiso 1 1 d . . . . . H10B H -0.269(2) 0.1272(19) 0.8911(19) 0.057(5) Uiso 1 1 d . . . . . H10C H -0.115(2) 0.007(2) 0.935(2) 0.062(5) Uiso 1 1 d . . . . . C11 C -0.21862(19) 0.35861(17) 0.44348(17) 0.0424(3) Uani 1 1 d . . . . . H11A H -0.175(2) 0.452(2) 0.4049(19) 0.054(5) Uiso 1 1 d . . . . . H11B H -0.335(3) 0.3627(19) 0.500(2) 0.058(5) Uiso 1 1 d . . . . . H11C H -0.229(2) 0.3309(19) 0.368(2) 0.055(5) Uiso 1 1 d . . . . . C12 C 0.47203(15) 0.25818(13) 0.26561(13) 0.0306(3) Uani 1 1 d . . . . . C13 C 0.46486(16) 0.38593(13) 0.27511(13) 0.0306(3) Uani 1 1 d . . . . . H13 H 0.3879(18) 0.4093(14) 0.3493(15) 0.029(3) Uiso 1 1 d . . . . . C14 C 0.57639(16) 0.49239(13) 0.17503(13) 0.0306(3) Uani 1 1 d . . . . . C15 C 0.57308(18) 0.62316(14) 0.18534(14) 0.0358(3) Uani 1 1 d . . . . . H15 H 0.489(2) 0.6433(15) 0.2594(17) 0.037(4) Uiso 1 1 d . . . . . C16 C 0.68406(19) 0.72330(15) 0.08861(15) 0.0409(3) Uani 1 1 d . . . . . H16 H 0.678(2) 0.8160(18) 0.0959(17) 0.047(4) Uiso 1 1 d . . . . . C17 C 0.80326(19) 0.69581(16) -0.02192(15) 0.0432(4) Uani 1 1 d . . . . . H17 H 0.885(2) 0.7696(19) -0.093(2) 0.057(5) Uiso 1 1 d . . . . . C18 C 0.80873(19) 0.57120(16) -0.03519(15) 0.0410(3) Uani 1 1 d . . . . . H18 H 0.891(2) 0.5482(17) -0.1086(18) 0.045(4) Uiso 1 1 d . . . . . C19 C 0.69539(17) 0.46516(14) 0.06331(13) 0.0342(3) Uani 1 1 d . . . . . C20 C 0.69774(19) 0.33361(15) 0.05402(15) 0.0399(3) Uani 1 1 d . . . . . H20 H 0.779(2) 0.3181(18) -0.0248(19) 0.051(5) Uiso 1 1 d . . . . . C21 C 0.59022(18) 0.23318(14) 0.15164(14) 0.0370(3) Uani 1 1 d . . . . . H21 H 0.591(2) 0.1405(19) 0.1424(19) 0.055(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 O1 0.0481(6) 0.0330(5) 0.0545(6) -0.0202(5) -0.0014(5) -0.0029(4) O2 0.0421(6) 0.0359(5) 0.0523(6) -0.0175(5) -0.0058(5) 0.0013(4) C1 0.0315(7) 0.0291(6) 0.0374(7) -0.0104(5) -0.0115(5) 0.0016(5) C2 0.0297(6) 0.0239(6) 0.0312(6) -0.0058(5) -0.0088(5) -0.0013(5) C3 0.0400(7) 0.0243(6) 0.0337(7) -0.0039(5) -0.0119(6) 0.0004(5) C4 0.0391(7) 0.0313(6) 0.0308(6) -0.0052(5) -0.0136(6) 0.0018(5) C5 0.0388(7) 0.0355(7) 0.0321(7) -0.0089(5) -0.0076(6) -0.0035(6) C6 0.0257(6) 0.0295(6) 0.0369(7) -0.0077(5) -0.0027(5) -0.0044(5) C7 0.0280(6) 0.0307(6) 0.0353(7) -0.0054(5) -0.0091(5) -0.0028(5) C8 0.0291(6) 0.0255(6) 0.0305(6) -0.0041(5) -0.0094(5) -0.0024(5) C9 0.0299(7) 0.0329(7) 0.0362(7) -0.0114(5) -0.0118(5) 0.0016(5) C10 0.0509(9) 0.0421(8) 0.0354(8) -0.0057(6) -0.0052(7) -0.0114(7) C11 0.0316(8) 0.0452(8) 0.0450(8) -0.0082(7) -0.0144(6) 0.0031(6) C12 0.0258(6) 0.0322(6) 0.0323(6) -0.0086(5) -0.0105(5) 0.0025(5) C13 0.0264(6) 0.0340(6) 0.0304(6) -0.0093(5) -0.0088(5) -0.0003(5) C14 0.0259(6) 0.0336(6) 0.0309(6) -0.0067(5) -0.0121(5) 0.0001(5) C15 0.0340(7) 0.0379(7) 0.0340(7) -0.0100(6) -0.0088(6) -0.0048(5) C16 0.0419(8) 0.0376(7) 0.0401(7) -0.0069(6) -0.0120(6) -0.0093(6) C17 0.0381(8) 0.0443(8) 0.0363(7) -0.0009(6) -0.0085(6) -0.0085(6) C18 0.0347(7) 0.0447(8) 0.0316(7) -0.0038(6) -0.0044(6) 0.0002(6) C19 0.0293(6) 0.0388(7) 0.0296(6) -0.0057(5) -0.0104(5) 0.0024(5) C20 0.0377(7) 0.0418(7) 0.0331(7) -0.0111(6) -0.0047(6) 0.0066(6) C21 0.0365(7) 0.0353(7) 0.0369(7) -0.0119(6) -0.0102(6) 0.0060(5) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 2 -1 0.0834 2 -2 1 0.1238 -1 0 2 0.0956 -1 -2 5 0.0904 1 -2 2 0.1133 2 -1 -1 0.0833 -1 1 6 0.0901 0 0 1 0.0987 0 0 -1 0.1046 1 6 5 0.0494 -1 -2 -2 0.0585 -5 -2 -3 0.0652 -4 4 2 0.0923 1 2 1 0.0621 -1 7 3 0.0668 -3 -5 0 0.0694 1 2 0 0.0850 1 6 0 0.0839 0 1 -1 0.0978 -1 1 0 0.0813 -3 1 -5 0.0894 2 5 6 0.0740 -5 0 -4 0.0653 -5 -3 -2 0.0652 -3 -4 1 0.0709 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 O1 C1 C2 119.87(12) . . ? O1 C1 C12 119.76(12) . . ? C12 C1 C2 120.34(11) . . ? C1 C2 C3 115.23(10) . . ? C1 C2 C8 108.24(10) . . ? C1 C2 C9 117.78(10) . . ? C3 C2 C9 87.54(9) . . ? C8 C2 C3 112.89(10) . . ? C8 C2 C9 114.15(10) . . ? C2 C3 H3A 110.6(9) . . ? C2 C3 H3B 116.6(9) . . ? H3A C3 H3B 108.8(12) . . ? C4 C3 C2 88.95(9) . . ? C4 C3 H3A 111.3(9) . . ? C4 C3 H3B 119.3(9) . . ? C3 C4 H4 114.0(9) . . ? C5 C4 C3 118.18(12) . . ? C5 C4 H4 107.6(9) . . ? C5 C4 C9 112.36(10) . . ? C9 C4 C3 88.27(10) . . ? C9 C4 H4 115.7(9) . . ? C4 C5 H5 109.0(9) . . ? C6 C5 C4 114.32(11) . . ? C6 C5 H5 105.3(8) . . ? C6 C5 C10 109.06(12) . . ? C10 C5 C4 112.71(12) . . ? C10 C5 H5 105.8(8) . . ? O2 C6 C5 119.45(12) . . ? O2 C6 C7 121.59(12) . . ? C7 C6 C5 118.89(11) . . ? C6 C7 H7 107.1(9) . . ? C6 C7 C8 111.87(10) . . ? C6 C7 C11 112.43(12) . . ? C8 C7 H7 107.5(9) . . ? C11 C7 H7 109.2(9) . . ? C11 C7 C8 108.62(11) . . ? C2 C8 H8A 110.3(9) . . ? C2 C8 H8B 108.9(9) . . ? C7 C8 C2 117.18(10) . . ? C7 C8 H8A 106.8(9) . . ? C7 C8 H8B 106.2(9) . . ? H8A C8 H8B 107.0(13) . . ? C2 C9 H9A 117.5(9) . . ? C2 C9 H9B 110.7(9) . . ? C4 C9 C2 88.55(9) . . ? C4 C9 H9A 115.8(9) . . ? C4 C9 H9B 110.6(9) . . ? H9A C9 H9B 111.7(13) . . ? C5 C10 H10A 110.8(10) . . ? C5 C10 H10B 109.7(10) . . ? C5 C10 H10C 107.5(11) . . ? H10A C10 H10B 106.6(14) . . ? H10A C10 H10C 111.4(14) . . ? H10B C10 H10C 110.9(15) . . ? C7 C11 H11A 110.7(11) . . ? C7 C11 H11B 113.3(11) . . ? C7 C11 H11C 110.0(11) . . ? H11A C11 H11B 106.3(15) . . ? H11A C11 H11C 109.6(15) . . ? H11B C11 H11C 106.9(15) . . ? C13 C12 C1 123.02(12) . . ? C13 C12 C21 119.32(12) . . ? C21 C12 C1 117.66(12) . . ? C12 C13 H13 123.3(8) . . ? C12 C13 C14 121.14(12) . . ? C14 C13 H13 115.5(8) . . ? C15 C14 C13 121.71(12) . . ? C15 C14 C19 119.43(12) . . ? C19 C14 C13 118.86(12) . . ? C14 C15 H15 119.6(9) . . ? C16 C15 C14 120.52(13) . . ? C16 C15 H15 119.8(9) . . ? C15 C16 H16 119.6(10) . . ? C15 C16 C17 120.03(14) . . ? C17 C16 H16 120.3(10) . . ? C16 C17 H17 119.7(11) . . ? C18 C17 C16 120.82(13) . . ? C18 C17 H17 119.5(11) . . ? C17 C18 H18 122.8(10) . . ? C17 C18 C19 120.56(14) . . ? C19 C18 H18 116.6(10) . . ? C14 C19 C18 118.64(13) . . ? C20 C19 C14 118.97(12) . . ? C20 C19 C18 122.39(13) . . ? C19 C20 H20 117.5(10) . . ? C21 C20 C19 121.01(13) . . ? C21 C20 H20 121.5(10) . . ? C12 C21 H21 119.2(10) . . ? C20 C21 C12 120.68(13) . . ? C20 C21 H21 120.1(10) . . ? 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 1.2223(16) . ? O2 C6 1.2158(16) . ? C1 C2 1.5177(18) . ? C1 C12 1.4967(18) . ? C2 C3 1.5504(17) . ? C2 C8 1.5412(17) . ? C2 C9 1.5638(18) . ? C3 H3A 0.975(16) . ? C3 H3B 1.001(16) . ? C3 C4 1.5482(19) . ? C4 H4 0.981(16) . ? C4 C5 1.5342(19) . ? C4 C9 1.5456(18) . ? C5 H5 1.048(16) . ? C5 C6 1.5224(18) . ? C5 C10 1.529(2) . ? C6 C7 1.5148(19) . ? C7 H7 0.996(16) . ? C7 C8 1.5402(18) . ? C7 C11 1.5215(18) . ? C8 H8A 0.993(16) . ? C8 H8B 0.984(16) . ? C9 H9A 1.010(16) . ? C9 H9B 0.976(16) . ? C10 H10A 1.057(19) . ? C10 H10B 1.036(19) . ? C10 H10C 1.01(2) . ? C11 H11A 0.976(19) . ? C11 H11B 0.98(2) . ? C11 H11C 0.991(19) . ? C12 C13 1.3728(18) . ? C12 C21 1.4234(19) . ? C13 H13 0.961(15) . ? C13 C14 1.4224(18) . ? C14 C15 1.4116(19) . ? C14 C19 1.4183(19) . ? C15 H15 0.969(16) . ? C15 C16 1.3722(19) . ? C16 H16 0.997(17) . ? C16 C17 1.411(2) . ? C17 H17 1.008(19) . ? C17 C18 1.360(2) . ? C18 H18 0.971(17) . ? C18 C19 1.4230(19) . ? C19 C20 1.416(2) . ? C20 H20 0.974(18) . ? C20 C21 1.362(2) . ? C21 H21 1.011(18) . ? 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 20.29(18) . . . . ? O1 C1 C2 C8 -107.15(13) . . . . ? O1 C1 C2 C9 121.52(14) . . . . ? O1 C1 C12 C13 -177.75(12) . . . . ? O1 C1 C12 C21 3.19(19) . . . . ? O2 C6 C7 C8 107.85(14) . . . . ? O2 C6 C7 C11 -14.70(17) . . . . ? C1 C2 C3 C4 139.01(11) . . . . ? C1 C2 C8 C7 161.02(11) . . . . ? C1 C2 C9 C4 -136.71(11) . . . . ? C1 C12 C13 C14 179.35(11) . . . . ? C1 C12 C21 C20 -179.68(12) . . . . ? C2 C1 C12 C13 4.22(19) . . . . ? C2 C1 C12 C21 -174.84(11) . . . . ? C2 C3 C4 C5 95.02(12) . . . . ? C2 C3 C4 C9 -19.53(10) . . . . ? C3 C2 C8 C7 32.25(15) . . . . ? C3 C2 C9 C4 -19.34(9) . . . . ? C3 C4 C5 C6 -59.27(16) . . . . ? C3 C4 C5 C10 66.01(15) . . . . ? C3 C4 C9 C2 19.36(9) . . . . ? C4 C5 C6 O2 -134.40(13) . . . . ? C4 C5 C6 C7 48.60(16) . . . . ? C5 C4 C9 C2 -100.54(12) . . . . ? C5 C6 C7 C8 -75.22(14) . . . . ? C5 C6 C7 C11 162.24(12) . . . . ? C6 C7 C8 C2 53.21(15) . . . . ? C8 C2 C3 C4 -95.93(12) . . . . ? C8 C2 C9 C4 94.70(11) . . . . ? C9 C2 C3 C4 19.31(10) . . . . ? C9 C2 C8 C7 -65.70(14) . . . . ? C9 C4 C5 C6 41.30(16) . . . . ? C9 C4 C5 C10 166.57(12) . . . . ? C10 C5 C6 O2 98.43(15) . . . . ? C10 C5 C6 C7 -78.58(15) . . . . ? C11 C7 C8 C2 177.90(11) . . . . ? C12 C1 C2 C3 -161.68(11) . . . . ? C12 C1 C2 C8 70.88(14) . . . . ? C12 C1 C2 C9 -60.45(15) . . . . ? C12 C13 C14 C15 -178.50(12) . . . . ? C12 C13 C14 C19 0.58(18) . . . . ? C13 C12 C21 C20 1.2(2) . . . . ? C13 C14 C15 C16 178.91(12) . . . . ? C13 C14 C19 C18 -178.91(12) . . . . ? C13 C14 C19 C20 0.83(18) . . . . ? C14 C15 C16 C17 -0.3(2) . . . . ? C14 C19 C20 C21 -1.2(2) . . . . ? C15 C14 C19 C18 0.20(18) . . . . ? C15 C14 C19 C20 179.94(12) . . . . ? C15 C16 C17 C18 0.8(2) . . . . ? C16 C17 C18 C19 -0.7(2) . . . . ? C17 C18 C19 C14 0.3(2) . . . . ? C17 C18 C19 C20 -179.47(13) . . . . ? C18 C19 C20 C21 178.51(13) . . . . ? C19 C14 C15 C16 -0.2(2) . . . . ? C19 C20 C21 C12 0.2(2) . . . . ? C21 C12 C13 C14 -1.61(19) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2.0000 2.0000 -1.0000 -0.1937 0.1689 0.4768 2.0000 -2.0000 1.0000 0.1937 -0.1689 -0.4768 -1.0000 0.0000 2.0000 0.2673 -0.2284 0.2212 -1.2270 -1.5207 5.0365 0.7084 -0.6716 0.2171 1.0000 -2.0000 2.0000 0.3188 -0.3281 -0.2787 2.0000 -1.0000 -1.0000 -0.0994 0.1094 -0.4480 -1.3374 1.0226 5.9015 0.8072 -0.3854 0.4471 -0.0000 -0.0000 1.0000 0.1421 -0.0691 0.0231 0.0000 0.0000 -1.0000 -0.1421 0.0691 -0.0231 1.4972 6.0492 5.2728 0.7220 0.6168 0.3135 -1.0000 -2.0000 -2.0000 -0.2838 -0.2317 -0.0212 -5.1616 -1.5210 -3.2021 -0.5296 -0.4564 0.7150 -3.6258 4.0836 1.7415 0.1501 0.1244 0.9808 1.0000 2.0000 1.0000 0.1416 0.3008 -0.0019 -0.5551 6.5925 2.7675 0.3262 0.6812 0.6554 -3.2992 -4.9004 -0.0747 -0.0238 -0.9778 0.2081 1.0000 2.0000 0.0000 -0.0005 0.3700 -0.0250 0.8331 6.3995 0.4673 0.0245 0.9383 0.3449 0.0000 1.0000 -1.0000 -0.1509 0.2091 0.0519 -1.0000 1.0000 0.0000 -0.0258 0.0499 0.2499 -3.0216 1.4060 -5.2433 -0.8090 0.2871 0.5129 2.1310 4.5536 6.4753 0.9168 0.3815 0.1183 -4.9768 -0.4052 -3.6969 -0.6066 -0.2494 0.7549 -4.7973 -3.2950 -1.5877 -0.2784 -0.7835 0.5556 -2.8296 -4.4133 1.3275 0.1793 -0.9643 0.1948