#------------------------------------------------------------------------------ #$Date: 2024-06-15 01:11:51 +0300 (Sat, 15 Jun 2024) $ #$Revision: 292401 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571892.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_1571892 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 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 difmap _atom_sites_solution_primary dual _audit_creation_date 2024-05-21 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-05-21 deposited with the CCDC. 2024-06-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.9318(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.7615(2) _cell_length_b 6.40467(8) _cell_length_c 13.86477(15) _cell_measurement_reflns_used 4923 _cell_measurement_temperature 140.00(10) _cell_measurement_theta_max 75.3010 _cell_measurement_theta_min 5.0060 _cell_volume 1568.76(3) _computing_cell_refinement 'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.123a 64-bit (release 20-05-2024))' _computing_data_reduction 'CrysAlisPro 1.171.43.123a (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 'CCD plate' _diffrn_detector_area_resol_mean 5.2817 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.983 _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 -58.00 31.00 1.00 2.00 -- -40.91 56.00-122.00 89 2 \w -112.00 -19.00 1.00 2.00 -- -40.91 -56.00 95.00 93 3 \w 91.00 171.00 1.00 8.00 -- 112.00 56.00-122.00 80 4 \w 56.00 127.00 1.00 8.00 -- 112.00 -56.00 95.00 71 5 \w 13.00 75.00 1.00 2.00 -- 40.91 -99.00 -60.00 62 6 \w 55.00 94.00 1.00 2.00 -- 40.91-125.00 60.00 39 7 \w 85.00 110.00 1.00 8.00 -- 112.00 30.00-150.00 25 8 \w 105.00 131.00 1.00 8.00 -- 112.00 77.00 120.00 26 9 \w 145.00 175.00 1.00 8.00 -- 112.00 77.00 120.00 30 10 \w 105.00 168.00 1.00 8.00 -- 112.00 111.00-120.00 63 11 \w 105.00 177.00 1.00 8.00 -- 112.00 61.00 150.00 72 12 \w 153.00 178.00 1.00 8.00 -- 112.00 30.00-150.00 25 13 \w 45.00 92.00 1.00 8.00 -- 112.00-111.00 60.00 47 14 \w 39.00 105.00 1.00 8.00 -- 112.00-111.00 90.00 66 15 \w 97.00 149.00 1.00 8.00 -- 112.00 45.00-150.00 52 16 \w 133.00 166.00 1.00 8.00 -- 112.00 111.00-150.00 33 17 \w 108.00 143.00 1.00 8.00 -- 112.00 111.00 150.00 35 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0644620000 _diffrn_orient_matrix_UB_12 -0.1574801000 _diffrn_orient_matrix_UB_13 0.0089572000 _diffrn_orient_matrix_UB_21 -0.0293318000 _diffrn_orient_matrix_UB_22 0.0377697000 _diffrn_orient_matrix_UB_23 -0.1070749000 _diffrn_orient_matrix_UB_31 0.0508459000 _diffrn_orient_matrix_UB_32 -0.1779010000 _diffrn_orient_matrix_UB_33 -0.0305985000 _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 0.0228 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7738 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.026 _diffrn_reflns_theta_min 5.007 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.640 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.643 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.123a (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 1.297 _exptl_crystal_description prism _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.673 _exptl_crystal_size_mid 0.234 _exptl_crystal_size_min 0.097 _refine_diff_density_max 0.271 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef 0.0008(3) _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 1.042 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 3208 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0660P)^2^+0.2959P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1060 _refine_ls_wR_factor_ref 0.1104 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2925 _reflns_number_total 3208 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02767a2.cif _cod_data_source_block ste-24-1162 _cod_database_code 1571892 _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 0.941 _shelx_estimated_absorpt_t_min 0.673 _olex2_refinement_description ; ; _shelx_res_file ; TITL STE-24-1162 in P2(1)/c ste-24-1162.res created by SHELXL-2019/3 at 14:52:22 on 21-May-2024 CELL 1.54184 17.7615 6.40467 13.86477 90 95.9318 90 ZERR 4 0.0002 0.00008 0.00015 0 0.0011 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 84 88 8 L.S. 10 PLAN 10 SIZE 0.673 0.234 0.097 TEMP -133 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.066000 0.295900 EXTI 0.000840 FVAR 4.89584 O1 3 0.941791 0.420028 0.814190 11.00000 0.03328 0.03376 = 0.03226 0.00400 -0.01188 0.00008 O2 3 0.753313 -0.034953 0.509735 11.00000 0.03065 0.02012 = 0.04895 -0.00334 -0.00740 -0.00119 C1 1 0.923573 0.467317 0.730109 11.00000 0.02323 0.01824 = 0.03020 -0.00010 -0.00717 -0.00349 C2 1 0.976596 0.436088 0.652761 11.00000 0.01826 0.02736 = 0.03914 0.00114 -0.00362 -0.00155 H2A 2 0.991905 0.573653 0.631851 11.00000 0.03660 H2B 2 1.022177 0.367574 0.681413 11.00000 0.03817 C3 1 0.943318 0.304867 0.566284 11.00000 0.01902 0.02923 = 0.03380 -0.00121 0.00305 -0.00024 H3 2 0.982524 0.259821 0.528823 11.00000 0.02828 C4 1 0.891163 0.127463 0.595906 11.00000 0.02047 0.02145 = 0.03475 -0.00122 -0.00166 0.00198 H4A 2 0.898842 0.077931 0.664532 11.00000 0.03183 H4B 2 0.891498 0.005836 0.552640 11.00000 0.03328 C5 1 0.821248 0.269430 0.566515 11.00000 0.01846 0.01860 = 0.02311 0.00098 -0.00137 -0.00040 C6 1 0.791053 0.391607 0.651298 11.00000 0.01888 0.01913 = 0.02094 0.00180 -0.00190 -0.00013 H6 2 0.746947 0.472724 0.622243 11.00000 0.02091 C7 1 0.846207 0.560988 0.697997 11.00000 0.02293 0.01925 = 0.02290 0.00075 -0.00314 0.00035 H7 2 0.852803 0.666277 0.647182 11.00000 0.02570 C8 1 0.873694 0.399643 0.504615 11.00000 0.02291 0.02765 = 0.02431 0.00046 0.00230 -0.00305 H8A 2 0.868009 0.550256 0.502210 11.00000 0.02640 H8B 2 0.870604 0.350019 0.439331 11.00000 0.03047 C9 1 0.765625 0.239447 0.726774 11.00000 0.02731 0.02674 = 0.02535 0.00499 0.00088 -0.00333 H9A 2 0.737623 0.307241 0.774329 11.00000 0.03969 H9B 2 0.731593 0.132085 0.695760 11.00000 0.03994 H9C 2 0.807517 0.163978 0.763529 11.00000 0.02956 C10 1 0.813128 0.673248 0.781204 11.00000 0.03171 0.02880 = 0.02979 -0.00603 -0.00136 0.00182 H10A 2 0.811081 0.584067 0.838973 11.00000 0.04374 H10B 2 0.843831 0.801380 0.800304 11.00000 0.03999 H10C 2 0.759969 0.718377 0.761132 11.00000 0.04509 C11 1 0.754847 0.154712 0.511746 11.00000 0.02180 0.02094 = 0.02399 -0.00159 0.00006 -0.00165 C12 1 0.688796 0.277179 0.464256 11.00000 0.02196 0.02237 = 0.01829 -0.00276 -0.00119 -0.00082 C13 1 0.694584 0.488202 0.434637 11.00000 0.02304 0.02290 = 0.02245 -0.00165 -0.00031 -0.00357 H13 2 0.741360 0.559956 0.442586 11.00000 0.02975 C14 1 0.632418 0.591016 0.391551 11.00000 0.02937 0.02190 = 0.02345 0.00022 -0.00003 -0.00013 H14 2 0.636513 0.729974 0.370804 11.00000 0.03068 C15 1 0.560383 0.493161 0.379056 11.00000 0.02458 0.02945 = 0.01772 -0.00276 -0.00034 0.00207 C16 1 0.494264 0.599103 0.338447 11.00000 0.03002 0.03503 = 0.02492 -0.00075 -0.00100 0.00675 H16 2 0.499425 0.737981 0.315671 11.00000 0.03197 C17 1 0.425287 0.501492 0.331524 11.00000 0.02466 0.05011 = 0.02883 -0.00142 -0.00302 0.00853 H17 2 0.381816 0.578948 0.305595 11.00000 0.04643 C18 1 0.418626 0.293872 0.362580 11.00000 0.02214 0.05229 = 0.02875 -0.00315 -0.00167 -0.00368 H18 2 0.368439 0.225142 0.358320 11.00000 0.04606 C19 1 0.481658 0.185578 0.399520 11.00000 0.02391 0.03774 = 0.02460 -0.00180 -0.00117 -0.00548 H19 2 0.478342 0.040841 0.419466 11.00000 0.03257 C20 1 0.553946 0.283086 0.409516 11.00000 0.02187 0.02986 = 0.01775 -0.00359 -0.00086 -0.00223 C21 1 0.619723 0.177442 0.450284 11.00000 0.02406 0.02237 = 0.02045 -0.00179 -0.00036 -0.00306 H21 2 0.615662 0.037077 0.470684 11.00000 0.02356 HKLF 4 REM STE-24-1162 in P2(1)/c REM wR2 = 0.1104, GooF = S = 1.042, Restrained GooF = 1.042 for all data REM R1 = 0.0405 for 2925 Fo > 4sig(Fo) and 0.0442 for all 3208 data REM 297 parameters refined using 0 restraints END WGHT 0.0660 0.2959 REM Highest difference peak 0.271, deepest hole -0.203, 1-sigma level 0.047 Q1 1 0.8377 0.3475 0.5345 11.00000 0.05 0.27 Q2 1 0.9215 0.2071 0.5795 11.00000 0.05 0.25 Q3 1 0.7762 0.3305 0.6932 11.00000 0.05 0.25 Q4 1 0.9471 0.4421 0.6881 11.00000 0.05 0.25 Q5 1 0.8035 0.3231 0.6085 11.00000 0.05 0.25 Q6 1 0.6927 0.3774 0.4517 11.00000 0.05 0.24 Q7 1 0.5569 0.3814 0.3986 11.00000 0.05 0.24 Q8 1 0.7885 0.2175 0.5402 11.00000 0.05 0.23 Q9 1 0.8528 0.1968 0.5833 11.00000 0.05 0.23 Q10 1 0.9574 0.3644 0.6192 11.00000 0.05 0.21 ; _shelx_res_checksum 71283 _olex2_date_sample_data_collection 2024-05-21 _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 6.825 _oxdiff_exptl_absorpt_empirical_full_min 0.492 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 0.94179(5) 0.42003(15) 0.81419(6) 0.0342(2) Uani 1 1 d . . . . . O2 O 0.75331(5) -0.03495(14) 0.50973(7) 0.0340(2) Uani 1 1 d . . . . . C1 C 0.92357(6) 0.46732(17) 0.73011(8) 0.0246(2) Uani 1 1 d . . . . . C2 C 0.97660(6) 0.43609(19) 0.65276(9) 0.0287(3) Uani 1 1 d . . . . . H2A H 0.9919(9) 0.574(3) 0.6319(12) 0.037(4) Uiso 1 1 d . . . . . H2B H 1.0222(10) 0.368(3) 0.6814(12) 0.038(4) Uiso 1 1 d . . . . . C3 C 0.94332(6) 0.30487(19) 0.56628(9) 0.0273(3) Uani 1 1 d . . . . . H3 H 0.9825(9) 0.260(2) 0.5288(11) 0.028(4) Uiso 1 1 d . . . . . C4 C 0.89116(6) 0.12746(18) 0.59591(9) 0.0259(2) Uani 1 1 d . . . . . H4A H 0.8988(9) 0.078(3) 0.6645(12) 0.032(4) Uiso 1 1 d . . . . . H4B H 0.8915(9) 0.006(3) 0.5526(12) 0.033(4) Uiso 1 1 d . . . . . C5 C 0.82125(6) 0.26943(16) 0.56652(7) 0.0203(2) Uani 1 1 d . . . . . C6 C 0.79105(5) 0.39161(16) 0.65130(7) 0.0199(2) Uani 1 1 d . . . . . H6 H 0.7469(8) 0.473(2) 0.6222(10) 0.021(3) Uiso 1 1 d . . . . . C7 C 0.84621(6) 0.56099(17) 0.69800(7) 0.0221(2) Uani 1 1 d . . . . . H7 H 0.8528(8) 0.666(2) 0.6472(11) 0.026(3) Uiso 1 1 d . . . . . C8 C 0.87369(6) 0.39964(18) 0.50461(8) 0.0250(2) Uani 1 1 d . . . . . H8A H 0.8680(8) 0.550(3) 0.5022(11) 0.026(3) Uiso 1 1 d . . . . . H8B H 0.8706(9) 0.350(3) 0.4393(11) 0.030(4) Uiso 1 1 d . . . . . C9 C 0.76563(6) 0.23945(19) 0.72677(8) 0.0266(2) Uani 1 1 d . . . . . H9A H 0.7376(10) 0.307(3) 0.7743(13) 0.040(4) Uiso 1 1 d . . . . . H9B H 0.7316(10) 0.132(3) 0.6958(12) 0.040(4) Uiso 1 1 d . . . . . H9C H 0.8075(9) 0.164(3) 0.7635(11) 0.030(4) Uiso 1 1 d . . . . . C10 C 0.81313(7) 0.6732(2) 0.78120(9) 0.0304(3) Uani 1 1 d . . . . . H10A H 0.8111(10) 0.584(3) 0.8390(14) 0.044(4) Uiso 1 1 d . . . . . H10B H 0.8438(10) 0.801(3) 0.8003(12) 0.040(4) Uiso 1 1 d . . . . . H10C H 0.7600(10) 0.718(3) 0.7611(13) 0.045(5) Uiso 1 1 d . . . . . C11 C 0.75485(6) 0.15471(17) 0.51175(7) 0.0224(2) Uani 1 1 d . . . . . C12 C 0.68880(6) 0.27718(17) 0.46426(7) 0.0211(2) Uani 1 1 d . . . . . C13 C 0.69458(6) 0.48820(17) 0.43464(7) 0.0230(2) Uani 1 1 d . . . . . H13 H 0.7414(9) 0.560(3) 0.4426(11) 0.030(4) Uiso 1 1 d . . . . . C14 C 0.63242(6) 0.59102(18) 0.39155(8) 0.0251(2) Uani 1 1 d . . . . . H14 H 0.6365(9) 0.730(3) 0.3708(11) 0.031(4) Uiso 1 1 d . . . . . C15 C 0.56038(6) 0.49316(19) 0.37906(7) 0.0241(2) Uani 1 1 d . . . . . C16 C 0.49426(7) 0.5991(2) 0.33845(8) 0.0303(3) Uani 1 1 d . . . . . H16 H 0.4994(9) 0.738(3) 0.3157(11) 0.032(4) Uiso 1 1 d . . . . . C17 C 0.42529(7) 0.5015(2) 0.33152(9) 0.0349(3) Uani 1 1 d . . . . . H17 H 0.3818(11) 0.579(3) 0.3056(13) 0.046(5) Uiso 1 1 d . . . . . C18 C 0.41863(7) 0.2939(2) 0.36258(9) 0.0347(3) Uani 1 1 d . . . . . H18 H 0.3684(11) 0.225(3) 0.3583(13) 0.046(5) Uiso 1 1 d . . . . . C19 C 0.48166(6) 0.1856(2) 0.39952(8) 0.0290(3) Uani 1 1 d . . . . . H19 H 0.4783(9) 0.041(3) 0.4195(11) 0.033(4) Uiso 1 1 d . . . . . C20 C 0.55395(6) 0.28309(18) 0.40952(7) 0.0234(2) Uani 1 1 d . . . . . C21 C 0.61972(6) 0.17744(17) 0.45028(7) 0.0225(2) Uani 1 1 d . . . . . H21 H 0.6157(8) 0.037(2) 0.4707(10) 0.024(3) 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 0.0333(4) 0.0338(5) 0.0323(4) 0.0040(3) -0.0119(3) 0.0001(4) O2 0.0306(4) 0.0201(4) 0.0489(5) -0.0033(3) -0.0074(4) -0.0012(3) C1 0.0232(5) 0.0182(5) 0.0302(5) -0.0001(4) -0.0072(4) -0.0035(4) C2 0.0183(5) 0.0274(6) 0.0391(6) 0.0011(5) -0.0036(4) -0.0016(4) C3 0.0190(5) 0.0292(6) 0.0338(6) -0.0012(4) 0.0030(4) -0.0002(4) C4 0.0205(5) 0.0214(5) 0.0347(6) -0.0012(4) -0.0017(4) 0.0020(4) C5 0.0185(5) 0.0186(5) 0.0231(5) 0.0010(4) -0.0014(4) -0.0004(4) C6 0.0189(4) 0.0191(5) 0.0209(5) 0.0018(4) -0.0019(4) -0.0001(4) C7 0.0229(5) 0.0193(5) 0.0229(5) 0.0008(4) -0.0031(4) 0.0003(4) C8 0.0229(5) 0.0276(6) 0.0243(5) 0.0005(4) 0.0023(4) -0.0030(4) C9 0.0273(5) 0.0267(6) 0.0253(5) 0.0050(4) 0.0009(4) -0.0033(4) C10 0.0317(6) 0.0288(6) 0.0298(6) -0.0060(5) -0.0014(4) 0.0018(5) C11 0.0218(5) 0.0209(5) 0.0240(5) -0.0016(4) 0.0001(4) -0.0017(4) C12 0.0220(5) 0.0224(5) 0.0183(4) -0.0028(4) -0.0012(4) -0.0008(4) C13 0.0230(5) 0.0229(5) 0.0224(5) -0.0017(4) -0.0003(4) -0.0036(4) C14 0.0294(5) 0.0219(5) 0.0234(5) 0.0002(4) 0.0000(4) -0.0001(4) C15 0.0246(5) 0.0294(6) 0.0177(4) -0.0028(4) -0.0003(4) 0.0021(4) C16 0.0300(6) 0.0350(7) 0.0249(5) -0.0007(4) -0.0010(4) 0.0067(5) C17 0.0247(5) 0.0501(8) 0.0288(6) -0.0014(5) -0.0030(4) 0.0085(5) C18 0.0221(5) 0.0523(8) 0.0287(6) -0.0031(5) -0.0017(4) -0.0037(5) C19 0.0239(5) 0.0377(7) 0.0246(5) -0.0018(4) -0.0012(4) -0.0055(5) C20 0.0219(5) 0.0299(6) 0.0178(4) -0.0036(4) -0.0009(4) -0.0022(4) C21 0.0241(5) 0.0224(5) 0.0204(5) -0.0018(4) -0.0004(4) -0.0031(4) 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 -1 2 -2 0.3323 2 -2 1 0.3022 1 -2 2 0.2890 2 0 -1 0.0807 -2 -1 1 0.2571 1 2 -1 0.3215 -1 2 0 0.3093 1 0 0 0.0422 -1 0 0 0.0543 -2 -1 -1 0.3076 1 -2 -2 0.3495 9 2 2 0.1826 -11 1 1 0.0928 0 1 1 0.3027 -2 0 -1 0.0950 2 0 1 0.0487 0 0 -1 0.1318 0 0 1 0.1023 5 -2 7 0.1577 -2 -2 7 0.1878 -11 0 4 0.0672 -10 -1 4 0.1148 -11 -1 1 0.0622 -11 0 2 0.0433 1 0 -2 0.1167 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 121.58(10) . . ? O1 C1 C7 121.41(10) . . ? C2 C1 C7 117.00(9) . . ? C1 C2 H2A 107.7(10) . . ? C1 C2 H2B 108.9(10) . . ? C1 C2 C3 114.17(9) . . ? H2A C2 H2B 106.5(14) . . ? C3 C2 H2A 111.1(10) . . ? C3 C2 H2B 108.1(11) . . ? C2 C3 H3 110.3(9) . . ? C2 C3 C4 112.84(10) . . ? C2 C3 C8 115.94(9) . . ? C4 C3 H3 114.4(9) . . ? C4 C3 C8 88.20(8) . . ? C8 C3 H3 113.7(9) . . ? C3 C4 H4A 117.3(9) . . ? C3 C4 H4B 112.2(9) . . ? C3 C4 C5 89.13(8) . . ? H4A C4 H4B 108.7(13) . . ? C5 C4 H4A 117.4(9) . . ? C5 C4 H4B 110.9(10) . . ? C4 C5 C8 87.20(8) . . ? C6 C5 C4 115.09(8) . . ? C6 C5 C8 114.64(8) . . ? C11 C5 C4 113.80(9) . . ? C11 C5 C6 108.06(8) . . ? C11 C5 C8 117.13(9) . . ? C5 C6 H6 106.1(8) . . ? C5 C6 C7 114.46(8) . . ? C7 C6 H6 103.9(8) . . ? C9 C6 C5 110.23(9) . . ? C9 C6 H6 109.6(8) . . ? C9 C6 C7 112.11(8) . . ? C1 C7 C6 110.91(8) . . ? C1 C7 H7 107.8(8) . . ? C1 C7 C10 111.74(9) . . ? C6 C7 H7 107.1(9) . . ? C10 C7 C6 111.56(9) . . ? C10 C7 H7 107.4(9) . . ? C3 C8 C5 88.57(8) . . ? C3 C8 H8A 118.8(9) . . ? C3 C8 H8B 110.9(9) . . ? C5 C8 H8A 118.8(8) . . ? C5 C8 H8B 111.2(10) . . ? H8A C8 H8B 107.6(13) . . ? C6 C9 H9A 112.8(11) . . ? C6 C9 H9B 110.9(10) . . ? C6 C9 H9C 113.9(9) . . ? H9A C9 H9B 106.0(14) . . ? H9A C9 H9C 106.4(13) . . ? H9B C9 H9C 106.3(14) . . ? C7 C10 H10A 112.9(11) . . ? C7 C10 H10B 110.0(9) . . ? C7 C10 H10C 110.6(10) . . ? H10A C10 H10B 108.8(14) . . ? H10A C10 H10C 106.3(15) . . ? H10B C10 H10C 108.0(15) . . ? O2 C11 C5 120.51(10) . . ? O2 C11 C12 119.75(10) . . ? C12 C11 C5 119.66(9) . . ? C13 C12 C11 123.11(9) . . ? C21 C12 C11 117.51(10) . . ? C21 C12 C13 119.37(10) . . ? C12 C13 H13 121.2(10) . . ? C14 C13 C12 120.34(10) . . ? C14 C13 H13 118.4(10) . . ? C13 C14 H14 120.3(9) . . ? C13 C14 C15 121.15(10) . . ? C15 C14 H14 118.5(9) . . ? C14 C15 C16 122.35(11) . . ? C20 C15 C14 118.82(10) . . ? C20 C15 C16 118.82(10) . . ? C15 C16 H16 118.3(10) . . ? C17 C16 C15 120.42(12) . . ? C17 C16 H16 121.3(9) . . ? C16 C17 H17 118.1(12) . . ? C16 C17 C18 120.86(11) . . ? C18 C17 H17 121.0(12) . . ? C17 C18 H18 120.4(11) . . ? C19 C18 C17 120.10(11) . . ? C19 C18 H18 119.5(11) . . ? C18 C19 H19 121.2(9) . . ? C18 C19 C20 120.58(12) . . ? C20 C19 H19 118.2(9) . . ? C15 C20 C19 119.18(10) . . ? C21 C20 C15 118.91(10) . . ? C21 C20 C19 121.90(11) . . ? C12 C21 C20 121.33(10) . . ? C12 C21 H21 119.5(9) . . ? C20 C21 H21 119.2(9) . . ? 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 1.2155(15) . ? O2 C11 1.2153(15) . ? C1 C2 1.5119(16) . ? C1 C7 1.5231(14) . ? C2 H2A 0.975(19) . ? C2 H2B 0.969(18) . ? C2 C3 1.5319(16) . ? C3 H3 0.955(15) . ? C3 C4 1.5480(16) . ? C3 C8 1.5525(15) . ? C4 H4A 0.999(16) . ? C4 H4B 0.984(18) . ? C4 C5 1.5589(14) . ? C5 C6 1.5531(14) . ? C5 C8 1.5701(14) . ? C5 C11 1.5239(14) . ? C6 H6 0.990(14) . ? C6 C7 1.5571(14) . ? C6 C9 1.5318(14) . ? C7 H7 0.991(15) . ? C7 C10 1.5275(15) . ? C8 H8A 0.970(17) . ? C8 H8B 0.956(16) . ? C9 H9A 0.969(18) . ? C9 H9B 0.985(19) . ? C9 H9C 0.984(16) . ? C10 H10A 0.987(19) . ? C10 H10B 1.006(19) . ? C10 H10C 0.999(19) . ? C11 C12 1.5051(14) . ? C12 C13 1.4194(16) . ? C12 C21 1.3790(15) . ? C13 H13 0.946(16) . ? C13 C14 1.3687(16) . ? C14 H14 0.940(17) . ? C14 C15 1.4191(16) . ? C15 C16 1.4212(16) . ? C15 C20 1.4183(17) . ? C16 H16 0.951(17) . ? C16 C17 1.3699(19) . ? C17 H17 0.96(2) . ? C17 C18 1.406(2) . ? C18 H18 0.990(19) . ? C18 C19 1.3705(18) . ? C19 H19 0.971(18) . ? C19 C20 1.4216(15) . ? C20 C21 1.4162(15) . ? C21 H21 0.947(16) . ? 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 124.70(12) . . . . ? O1 C1 C7 C6 -99.59(12) . . . . ? O1 C1 C7 C10 25.57(14) . . . . ? O2 C11 C12 C13 -158.41(11) . . . . ? O2 C11 C12 C21 22.18(15) . . . . ? C1 C2 C3 C4 -35.59(13) . . . . ? C1 C2 C3 C8 64.02(13) . . . . ? C2 C1 C7 C6 80.46(11) . . . . ? C2 C1 C7 C10 -154.38(10) . . . . ? C2 C3 C4 C5 97.67(10) . . . . ? C2 C3 C8 C5 -94.93(10) . . . . ? C3 C4 C5 C6 -96.36(10) . . . . ? C3 C4 C5 C8 19.61(8) . . . . ? C3 C4 C5 C11 138.13(9) . . . . ? C4 C3 C8 C5 19.69(8) . . . . ? C4 C5 C6 C7 66.56(11) . . . . ? C4 C5 C6 C9 -60.91(11) . . . . ? C4 C5 C8 C3 -19.56(8) . . . . ? C4 C5 C11 O2 13.48(14) . . . . ? C4 C5 C11 C12 -169.76(9) . . . . ? C5 C6 C7 C1 -54.25(11) . . . . ? C5 C6 C7 C10 -179.52(9) . . . . ? C5 C11 C12 C13 24.80(14) . . . . ? C5 C11 C12 C21 -154.60(10) . . . . ? C6 C5 C8 C3 96.84(9) . . . . ? C6 C5 C11 O2 -115.68(11) . . . . ? C6 C5 C11 C12 61.09(11) . . . . ? C7 C1 C2 C3 -55.35(13) . . . . ? C8 C3 C4 C5 -19.83(8) . . . . ? C8 C5 C6 C7 -32.38(12) . . . . ? C8 C5 C6 C9 -159.85(9) . . . . ? C8 C5 C11 O2 113.03(12) . . . . ? C8 C5 C11 C12 -70.20(12) . . . . ? C9 C6 C7 C1 72.25(11) . . . . ? C9 C6 C7 C10 -53.02(12) . . . . ? C11 C5 C6 C7 -165.01(8) . . . . ? C11 C5 C6 C9 67.51(10) . . . . ? C11 C5 C8 C3 -134.96(9) . . . . ? C11 C12 C13 C14 179.82(9) . . . . ? C11 C12 C21 C20 177.59(9) . . . . ? C12 C13 C14 C15 2.63(16) . . . . ? C13 C12 C21 C20 -1.84(15) . . . . ? C13 C14 C15 C16 177.19(10) . . . . ? C13 C14 C15 C20 -1.85(16) . . . . ? C14 C15 C16 C17 -177.19(11) . . . . ? C14 C15 C20 C19 178.42(10) . . . . ? C14 C15 C20 C21 -0.73(15) . . . . ? C15 C16 C17 C18 -1.24(18) . . . . ? C15 C20 C21 C12 2.57(15) . . . . ? C16 C15 C20 C19 -0.65(15) . . . . ? C16 C15 C20 C21 -179.80(9) . . . . ? C16 C17 C18 C19 -0.63(19) . . . . ? C17 C18 C19 C20 1.83(18) . . . . ? C18 C19 C20 C15 -1.18(16) . . . . ? C18 C19 C20 C21 177.95(10) . . . . ? C19 C20 C21 C12 -176.55(10) . . . . ? C20 C15 C16 C17 1.85(16) . . . . ? C21 C12 C13 C14 -0.78(15) . . . . ? 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 -1.0000 2.0000 -2.0000 -0.2684 0.3190 -0.3455 2.0000 -2.0000 1.0000 0.1950 -0.2413 0.4269 1.0000 -2.0000 2.0000 0.2684 -0.3190 0.3455 2.0000 -0.0000 -1.0000 -0.1379 0.0484 0.1323 -2.0000 -1.0000 1.0000 0.2954 -0.0862 0.0456 1.0000 2.0000 -1.0000 -0.3884 0.1533 -0.2744 -1.0000 2.0000 -0.0000 -0.2505 0.1049 -0.4066 1.0000 -0.0000 0.0000 -0.0645 -0.0293 0.0508 -1.0000 0.0000 -0.0000 0.0645 0.0293 -0.0508 -2.0000 -1.0000 -1.0000 0.2774 0.1280 0.1068 1.0000 -2.0000 -2.0000 0.2326 0.1093 0.4678 8.6904 2.4170 2.0457 -0.9225 -0.3827 -0.0507 -11.3654 0.7036 0.9129 0.6300 0.2622 -0.7310 -0.0000 1.0000 1.0000 -0.1485 -0.0693 -0.2085 -2.0000 -0.0000 -1.0000 0.1200 0.1657 -0.0711 2.0000 0.0000 1.0000 -0.1200 -0.1657 0.0711 0.0000 -0.0000 -1.0000 -0.0090 0.1071 0.0306 -0.0000 0.0000 1.0000 0.0090 -0.1071 -0.0306 4.5006 -1.9275 6.7544 0.0739 -0.9280 0.3651 -1.7599 -2.4400 7.2565 0.5627 -0.8175 0.1226 -10.5283 0.0667 4.4991 0.7085 -0.1704 -0.6849 -10.0519 -1.2393 4.2925 0.8816 -0.2116 -0.4220 -11.4058 -0.5546 1.4829 0.8359 0.1548 -0.5266 -11.4765 -0.0952 1.7784 0.7707 0.1426 -0.6210 1.0000 -0.0000 -2.0000 -0.0824 0.1848 0.1120