#------------------------------------------------------------------------------ #$Date: 2024-07-27 03:50:06 +0300 (Sat, 27 Jul 2024) $ #$Revision: 293561 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/91/7249116.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_7249116 loop_ _publ_author_name 'Hoser, Anna A.' 'Zwolenik, Aleksandra' 'Makal, Anna Maria' _publ_section_title ; On the importance of low-frequency modes in predicting pressure-induced phase transitions ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/D4CP02368D _journal_year 2024 _chemical_formula_moiety 'C20 H14 O2' _chemical_formula_sum 'C20 H14 O2' _chemical_formula_weight 286.31 _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 direct _audit_creation_date 2024-01-17 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2024-02-13 deposited with the CCDC. 2024-07-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.4944(19) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.15110(13) _cell_length_b 10.90793(19) _cell_length_c 17.7744(3) _cell_measurement_reflns_used 19785 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 34.4320 _cell_measurement_theta_min 3.3090 _cell_volume 1353.63(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)' _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 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.949 _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 -52.00 43.00 0.50 80.00 -- 30.50 -49.00 90.00 190 2 \w -9.00 112.00 0.50 80.00 -- 30.50 49.00-122.00 242 3 \w -75.00 -39.00 0.50 80.00 -- -30.81 -49.00 90.00 72 4 \w -12.00 116.00 0.50 80.00 -- 30.50 77.00 90.00 256 5 \w 56.00 114.00 0.50 80.00 -- 30.50 178.00 90.00 116 6 \w -49.00 -23.00 0.50 80.00 -- 30.50 19.00-150.00 52 7 \w -12.00 78.00 0.50 80.00 -- 30.50 77.00 -60.00 180 8 \w -4.00 117.00 0.50 80.00 -- 30.50 19.00-150.00 242 9 \w -2.00 110.00 0.50 80.00 -- 30.50 57.00 60.00 224 10 \w -126.00 -61.00 0.50 80.00 -- -30.81 178.00 -90.00 130 11 \w -124.00 -63.00 0.50 80.00 -- -30.81-178.00-180.00 122 12 \w -116.00 8.00 0.50 80.00 -- -30.81 -38.00 -90.00 248 13 \w -118.00 54.00 0.50 80.00 -- -30.81 19.00-150.00 344 14 \w -126.00 -73.00 0.50 80.00 -- -30.81-178.00 30.00 106 15 \w -22.00 16.00 0.50 80.00 -- -30.81 -99.00 150.00 76 16 \w -38.00 43.00 0.50 80.00 -- -30.81 49.00-122.00 162 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0575942284 _diffrn_orient_matrix_UB_12 -0.0442814338 _diffrn_orient_matrix_UB_13 0.0234894896 _diffrn_orient_matrix_UB_21 0.0836230409 _diffrn_orient_matrix_UB_22 0.0287614565 _diffrn_orient_matrix_UB_23 -0.0069440485 _diffrn_orient_matrix_UB_31 0.0037924276 _diffrn_orient_matrix_UB_32 0.0379375689 _diffrn_orient_matrix_UB_33 0.0327143467 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_unetI/netI 0.0276 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.949 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 48392 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.949 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.567 _diffrn_reflns_theta_min 3.326 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018) 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 yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.405 _exptl_crystal_description irregular _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.173 _exptl_crystal_size_mid 0.141 _exptl_crystal_size_min 0.036 _refine_diff_density_max 0.471 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 5486 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0440 _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^)+(0.0803P)^2^+0.0475P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1198 _refine_ls_wR_factor_ref 0.1293 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4111 _reflns_number_total 5486 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cp02368d2.cif _cod_data_source_block 2oapb_100k_smart3_abs _cod_database_code 7249116 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C20 H14 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. ; _olex2_refinement_description ; ; _shelx_res_file ; TITL 2oAPb_100K_smart3_abs in P21/c #14 2oapb_100k_smart3_abs.res created by SHELXL-2018/3 at 16:40:36 on 23-Jan-2023 REM reset to P21/c #14 CELL 0.71073 7.151101 10.907931 17.774373 90 102.4944 90 ZERR 4 0.000131 0.000186 0.000342 0 0.0019 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 80 56 8 L.S. 20 PLAN 5 CONF BOND fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.080300 0.047500 FVAR 0.37168 C1 1 0.244754 0.984477 0.492825 11.00000 0.01407 0.01746 = 0.01593 -0.00123 0.00334 0.00131 C2 1 0.211880 0.856907 0.476738 11.00000 0.01571 0.01839 = 0.01551 -0.00260 0.00333 0.00022 C3 1 0.228656 1.069005 0.429944 11.00000 0.01448 0.02076 = 0.01739 0.00120 0.00338 0.00204 C4 1 0.319025 0.943024 0.631893 11.00000 0.01682 0.01707 = 0.01501 -0.00240 0.00389 0.00108 C5 1 0.299381 1.028652 0.570280 11.00000 0.01531 0.01566 = 0.01688 -0.00204 0.00378 0.00046 C6 1 0.282933 0.819338 0.614577 11.00000 0.01844 0.01641 = 0.01664 -0.00113 0.00376 0.00083 C7 1 0.235085 0.773872 0.539625 11.00000 0.01779 0.01617 = 0.01728 -0.00263 0.00382 0.00028 C8 1 0.267974 1.195686 0.444101 11.00000 0.01723 0.01925 = 0.02260 0.00257 0.00541 0.00223 C9 1 0.179517 1.026754 0.352628 11.00000 0.01641 0.02632 = 0.01707 0.00098 0.00303 0.00340 C10 1 0.317076 1.237335 0.522039 11.00000 0.02192 0.01681 = 0.02585 -0.00051 0.00566 -0.00026 C11 1 0.154901 0.818247 0.397790 11.00000 0.02113 0.02297 = 0.01762 -0.00495 0.00308 -0.00091 O12 3 0.470023 1.072989 0.735864 11.00000 0.03046 0.02314 = 0.01942 -0.00580 0.00261 -0.00335 C13 1 0.331034 1.158493 0.582200 11.00000 0.02158 0.01696 = 0.02089 -0.00299 0.00480 -0.00061 C14 1 0.140995 0.899214 0.338795 11.00000 0.02145 0.02840 = 0.01624 -0.00319 0.00261 0.00097 C15 1 0.172706 1.110116 0.291860 11.00000 0.02008 0.03464 = 0.01891 0.00575 0.00368 0.00517 C16 1 0.260222 1.276235 0.381730 11.00000 0.02068 0.02363 = 0.02879 0.00795 0.00697 0.00352 C17 1 0.385705 0.976830 0.714985 11.00000 0.01813 0.02080 = 0.01584 -0.00307 0.00345 0.00249 C18 1 0.224188 0.637288 0.529946 11.00000 0.02108 0.01694 = 0.02139 -0.00332 0.00291 -0.00001 O19 3 0.255460 0.586203 0.472581 11.00000 0.04502 0.02023 = 0.02743 -0.00765 0.01203 -0.00023 C20 1 0.213684 1.233195 0.306528 11.00000 0.02118 0.03285 = 0.02552 0.01185 0.00627 0.00570 C21 1 0.178645 0.561701 0.594884 11.00000 0.02838 0.01754 = 0.02592 0.00005 0.00565 -0.00023 C22 1 0.349241 0.887613 0.775319 11.00000 0.02898 0.02626 = 0.01643 0.00062 0.00420 -0.00110 H6 2 0.303473 0.758525 0.658296 11.00000 0.02703 H20 2 0.213348 1.290716 0.263454 11.00000 0.03962 H11 2 0.129795 0.730327 0.386927 11.00000 0.03569 H15 2 0.141397 1.077616 0.237215 11.00000 0.02763 H10 2 0.344344 1.325345 0.530713 11.00000 0.03468 H22A 2 0.428736 0.815018 0.776053 11.00000 0.05116 H13 2 0.367158 1.189114 0.634555 11.00000 0.02673 H22B 2 0.213438 0.861801 0.763809 11.00000 0.03253 H22C 2 0.379358 0.928610 0.825737 11.00000 0.03337 H16 2 0.295783 1.362630 0.392394 11.00000 0.03452 H14 2 0.104093 0.871758 0.283814 11.00000 0.02686 H21A 2 0.073644 0.597941 0.614012 11.00000 0.03638 H21B 2 0.142303 0.478648 0.574923 11.00000 0.04345 H21C 2 0.292219 0.554463 0.637869 11.00000 0.03757 HKLF 4 REM 2oAPb_100K_smart3_abs in P21/c #14 REM wR2 = 0.1293, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0440 for 4111 Fo > 4sig(Fo) and 0.0631 for all 5486 data REM 255 parameters refined using 0 restraints END WGHT 0.0803 0.0475 REM Highest difference peak 0.471, deepest hole -0.194, 1-sigma level 0.056 Q1 1 0.3010 0.8809 0.6225 11.00000 0.05 0.47 Q2 1 0.3072 0.9822 0.6013 11.00000 0.05 0.45 Q3 1 0.2261 1.0253 0.4598 11.00000 0.05 0.44 Q4 1 0.2446 1.1369 0.4379 11.00000 0.05 0.44 Q5 1 0.2237 0.8160 0.5058 11.00000 0.05 0.43 ; _shelx_res_checksum 12095 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 1.258 _oxdiff_exptl_absorpt_empirical_full_min 0.823 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 C1 C 0.24475(10) 0.98448(7) 0.49282(4) 0.01581(14) Uani 1 1 d . . . . . C2 C 0.21188(11) 0.85691(7) 0.47674(4) 0.01654(14) Uani 1 1 d . . . . . C3 C 0.22866(11) 1.06901(7) 0.42994(4) 0.01755(15) Uani 1 1 d . . . . . C4 C 0.31902(11) 0.94302(7) 0.63189(4) 0.01623(14) Uani 1 1 d . . . . . C5 C 0.29938(10) 1.02865(7) 0.57028(4) 0.01591(14) Uani 1 1 d . . . . . C6 C 0.28293(11) 0.81934(7) 0.61458(4) 0.01717(14) Uani 1 1 d . . . . . C7 C 0.23508(11) 0.77387(7) 0.53962(4) 0.01708(14) Uani 1 1 d . . . . . C8 C 0.26797(11) 1.19569(7) 0.44410(5) 0.01953(15) Uani 1 1 d . . . . . C9 C 0.17952(11) 1.02675(8) 0.35263(5) 0.02002(16) Uani 1 1 d . . . . . C10 C 0.31708(12) 1.23734(8) 0.52204(5) 0.02145(16) Uani 1 1 d . . . . . C11 C 0.15490(12) 0.81825(8) 0.39779(5) 0.02074(16) Uani 1 1 d . . . . . O12 O 0.47002(9) 1.07299(6) 0.73586(3) 0.02476(14) Uani 1 1 d . . . . . C13 C 0.33103(12) 1.15849(7) 0.58220(5) 0.01978(15) Uani 1 1 d . . . . . C14 C 0.14100(12) 0.89921(8) 0.33880(5) 0.02225(17) Uani 1 1 d . . . . . C15 C 0.17271(12) 1.11012(9) 0.29186(5) 0.02462(18) Uani 1 1 d . . . . . C16 C 0.26022(12) 1.27623(8) 0.38173(5) 0.02412(17) Uani 1 1 d . . . . . C17 C 0.38571(11) 0.97683(7) 0.71499(4) 0.01829(15) Uani 1 1 d . . . . . C18 C 0.22419(11) 0.63729(7) 0.52995(5) 0.02006(16) Uani 1 1 d . . . . . O19 O 0.25546(11) 0.58620(6) 0.47258(4) 0.03026(16) Uani 1 1 d . . . . . C20 C 0.21368(12) 1.23319(9) 0.30653(5) 0.02633(19) Uani 1 1 d . . . . . C21 C 0.17864(14) 0.56170(8) 0.59488(5) 0.02398(17) Uani 1 1 d . . . . . C22 C 0.34924(14) 0.88761(9) 0.77532(5) 0.02400(17) Uani 1 1 d . . . . . H6 H 0.3035(17) 0.7585(11) 0.6583(7) 0.027(3) Uiso 1 1 d . . . . . H20 H 0.2133(19) 1.2907(12) 0.2635(7) 0.040(3) Uiso 1 1 d . . . . . H11 H 0.1298(18) 0.7303(12) 0.3869(7) 0.036(3) Uiso 1 1 d . . . . . H15 H 0.1414(18) 1.0776(11) 0.2372(7) 0.028(3) Uiso 1 1 d . . . . . H10 H 0.3443(18) 1.3253(12) 0.5307(7) 0.035(3) Uiso 1 1 d . . . . . H22A H 0.429(2) 0.8150(14) 0.7761(8) 0.051(4) Uiso 1 1 d . . . . . H13 H 0.3672(17) 1.1891(11) 0.6346(7) 0.027(3) Uiso 1 1 d . . . . . H22B H 0.2134(18) 0.8618(12) 0.7638(7) 0.033(3) Uiso 1 1 d . . . . . H22C H 0.3794(19) 0.9286(11) 0.8257(7) 0.033(3) Uiso 1 1 d . . . . . H16 H 0.2958(18) 1.3626(12) 0.3924(7) 0.035(3) Uiso 1 1 d . . . . . H14 H 0.1041(17) 0.8718(11) 0.2838(7) 0.027(3) Uiso 1 1 d . . . . . H21A H 0.0736(19) 0.5979(12) 0.6140(7) 0.036(3) Uiso 1 1 d . . . . . H21B H 0.142(2) 0.4786(13) 0.5749(7) 0.043(4) Uiso 1 1 d . . . . . H21C H 0.292(2) 0.5545(12) 0.6379(7) 0.038(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 C1 0.0141(3) 0.0175(3) 0.0159(3) -0.0012(2) 0.0033(2) 0.0013(2) C2 0.0157(3) 0.0184(3) 0.0155(3) -0.0026(2) 0.0033(2) 0.0002(3) C3 0.0145(3) 0.0208(3) 0.0174(3) 0.0012(3) 0.0034(2) 0.0020(3) C4 0.0168(3) 0.0171(3) 0.0150(3) -0.0024(2) 0.0039(2) 0.0011(2) C5 0.0153(3) 0.0157(3) 0.0169(3) -0.0020(2) 0.0038(2) 0.0005(2) C6 0.0184(3) 0.0164(3) 0.0166(3) -0.0011(3) 0.0038(3) 0.0008(2) C7 0.0178(3) 0.0162(3) 0.0173(3) -0.0026(2) 0.0038(3) 0.0003(2) C8 0.0172(3) 0.0192(3) 0.0226(4) 0.0026(3) 0.0054(3) 0.0022(3) C9 0.0164(3) 0.0263(4) 0.0171(3) 0.0010(3) 0.0030(3) 0.0034(3) C10 0.0219(4) 0.0168(3) 0.0258(4) -0.0005(3) 0.0057(3) -0.0003(3) C11 0.0211(4) 0.0230(4) 0.0176(3) -0.0049(3) 0.0031(3) -0.0009(3) O12 0.0305(3) 0.0231(3) 0.0194(3) -0.0058(2) 0.0026(2) -0.0034(2) C13 0.0216(3) 0.0170(3) 0.0209(4) -0.0030(3) 0.0048(3) -0.0006(3) C14 0.0214(4) 0.0284(4) 0.0162(3) -0.0032(3) 0.0026(3) 0.0010(3) C15 0.0201(4) 0.0346(5) 0.0189(4) 0.0058(3) 0.0037(3) 0.0052(3) C16 0.0207(4) 0.0236(4) 0.0288(4) 0.0079(3) 0.0070(3) 0.0035(3) C17 0.0181(3) 0.0208(3) 0.0158(3) -0.0031(3) 0.0034(3) 0.0025(3) C18 0.0211(4) 0.0169(3) 0.0214(4) -0.0033(3) 0.0029(3) 0.0000(3) O19 0.0450(4) 0.0202(3) 0.0274(3) -0.0077(2) 0.0120(3) -0.0002(3) C20 0.0212(4) 0.0328(5) 0.0255(4) 0.0119(3) 0.0063(3) 0.0057(3) C21 0.0284(4) 0.0175(3) 0.0259(4) 0.0001(3) 0.0056(3) -0.0002(3) C22 0.0290(4) 0.0263(4) 0.0164(4) 0.0006(3) 0.0042(3) -0.0011(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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 3 3 5 0.0480 -5 0 3 0.0571 -1 2 5 0.0569 -1 5 0 0.0068 1 -5 -1 0.0241 2 -9 -21 0.0669 3 -1 -5 0.0793 6 -6 -20 0.0754 10 1 -9 0.0779 5 3 1 0.0652 0 2 5 0.0607 -2 -4 -5 0.0757 -3 1 5 0.0622 -1 5 4 0.0255 0 -2 5 0.0854 0 2 -24 0.0701 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 C2 C1 C3 119.20(7) . . ? C2 C1 C5 121.27(7) . . ? C5 C1 C3 119.50(7) . . ? C1 C2 C11 118.71(7) . . ? C7 C2 C1 118.50(7) . . ? C7 C2 C11 122.78(7) . . ? C8 C3 C1 120.50(7) . . ? C9 C3 C1 120.46(7) . . ? C9 C3 C8 119.01(7) . . ? C5 C4 C17 123.72(7) . . ? C6 C4 C5 118.82(7) . . ? C6 C4 C17 117.39(7) . . ? C1 C5 C13 118.26(7) . . ? C4 C5 C1 118.71(7) . . ? C4 C5 C13 123.03(7) . . ? C4 C6 H6 118.5(7) . . ? C7 C6 C4 123.41(7) . . ? C7 C6 H6 117.9(7) . . ? C2 C7 C18 123.29(7) . . ? C6 C7 C2 119.23(7) . . ? C6 C7 C18 117.34(7) . . ? C3 C8 C10 118.60(7) . . ? C16 C8 C3 119.68(8) . . ? C16 C8 C10 121.71(8) . . ? C3 C9 C14 118.73(7) . . ? C15 C9 C3 119.63(8) . . ? C15 C9 C14 121.64(8) . . ? C8 C10 H10 117.4(7) . . ? C13 C10 C8 121.53(7) . . ? C13 C10 H10 121.0(7) . . ? C2 C11 H11 118.5(7) . . ? C14 C11 C2 121.40(8) . . ? C14 C11 H11 120.1(7) . . ? C5 C13 H13 118.7(7) . . ? C10 C13 C5 121.55(7) . . ? C10 C13 H13 119.7(7) . . ? C9 C14 H14 117.3(7) . . ? C11 C14 C9 121.40(7) . . ? C11 C14 H14 121.3(7) . . ? C9 C15 H15 118.3(7) . . ? C20 C15 C9 120.76(8) . . ? C20 C15 H15 120.9(7) . . ? C8 C16 H16 118.8(7) . . ? C20 C16 C8 120.56(8) . . ? C20 C16 H16 120.5(7) . . ? C4 C17 C22 118.32(7) . . ? O12 C17 C4 122.69(7) . . ? O12 C17 C22 118.99(7) . . ? C7 C18 C21 117.97(7) . . ? O19 C18 C7 122.23(8) . . ? O19 C18 C21 119.77(8) . . ? C15 C20 C16 120.37(8) . . ? C15 C20 H20 120.2(8) . . ? C16 C20 H20 119.4(8) . . ? C18 C21 H21A 110.8(7) . . ? C18 C21 H21B 108.1(8) . . ? C18 C21 H21C 110.9(8) . . ? H21A C21 H21B 109.6(11) . . ? H21A C21 H21C 109.2(10) . . ? H21B C21 H21C 108.2(11) . . ? C17 C22 H22A 110.1(9) . . ? C17 C22 H22B 110.4(7) . . ? C17 C22 H22C 108.4(7) . . ? H22A C22 H22B 108.4(12) . . ? H22A C22 H22C 110.2(11) . . ? H22B C22 H22C 109.3(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 C1 C2 1.4298(11) . ? C1 C3 1.4342(11) . ? C1 C5 1.4309(10) . ? C2 C7 1.4202(11) . ? C2 C11 1.4372(11) . ? C3 C8 1.4217(11) . ? C3 C9 1.4197(11) . ? C4 C5 1.4230(11) . ? C4 C6 1.3954(11) . ? C4 C17 1.4966(11) . ? C5 C13 1.4427(11) . ? C6 C7 1.3931(11) . ? C6 H6 1.008(12) . ? C7 C18 1.4998(11) . ? C8 C10 1.4277(12) . ? C8 C16 1.4062(11) . ? C9 C14 1.4291(12) . ? C9 C15 1.4047(12) . ? C10 C13 1.3590(11) . ? C10 H10 0.985(13) . ? C11 C14 1.3581(12) . ? C11 H11 0.987(13) . ? O12 C17 1.2266(10) . ? C13 H13 0.970(11) . ? C14 H14 1.001(12) . ? C15 C20 1.3868(14) . ? C15 H15 1.012(12) . ? C16 C20 1.3876(13) . ? C16 H16 0.984(13) . ? C17 C22 1.5120(12) . ? C18 O19 1.2243(10) . ? C18 C21 1.5102(12) . ? C20 H20 0.989(13) . ? C21 H21A 0.973(13) . ? C21 H21B 0.987(14) . ? C21 H21C 0.991(14) . ? C22 H22A 0.973(15) . ? C22 H22B 0.989(13) . ? C22 H22C 0.983(13) . ? 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 C1 C2 C7 C6 1.99(11) . . . . ? C1 C2 C7 C18 -173.59(7) . . . . ? C1 C2 C11 C14 3.21(12) . . . . ? C1 C3 C8 C10 -2.17(11) . . . . ? C1 C3 C8 C16 177.01(7) . . . . ? C1 C3 C9 C14 1.83(11) . . . . ? C1 C3 C9 C15 -177.20(7) . . . . ? C1 C5 C13 C10 -2.49(11) . . . . ? C2 C1 C3 C8 -177.47(7) . . . . ? C2 C1 C3 C9 0.39(11) . . . . ? C2 C1 C5 C4 -0.60(11) . . . . ? C2 C1 C5 C13 179.72(7) . . . . ? C2 C7 C18 O19 23.86(12) . . . . ? C2 C7 C18 C21 -157.99(7) . . . . ? C2 C11 C14 C9 -0.99(13) . . . . ? C3 C1 C2 C7 177.78(7) . . . . ? C3 C1 C2 C11 -2.86(11) . . . . ? C3 C1 C5 C4 -178.53(7) . . . . ? C3 C1 C5 C13 1.79(10) . . . . ? C3 C8 C10 C13 1.53(12) . . . . ? C3 C8 C16 C20 0.30(12) . . . . ? C3 C9 C14 C11 -1.56(12) . . . . ? C3 C9 C15 C20 0.09(12) . . . . ? C4 C5 C13 C10 177.85(7) . . . . ? C4 C6 C7 C2 -3.23(12) . . . . ? C4 C6 C7 C18 172.62(7) . . . . ? C5 C1 C2 C7 -0.15(11) . . . . ? C5 C1 C2 C11 179.21(7) . . . . ? C5 C1 C3 C8 0.50(11) . . . . ? C5 C1 C3 C9 178.36(7) . . . . ? C5 C4 C6 C7 2.45(12) . . . . ? C5 C4 C17 O12 -17.42(12) . . . . ? C5 C4 C17 C22 163.35(7) . . . . ? C6 C4 C5 C1 -0.48(11) . . . . ? C6 C4 C5 C13 179.18(7) . . . . ? C6 C4 C17 O12 159.59(8) . . . . ? C6 C4 C17 C22 -19.64(11) . . . . ? C6 C7 C18 O19 -151.80(8) . . . . ? C6 C7 C18 C21 26.35(11) . . . . ? C7 C2 C11 C14 -177.45(7) . . . . ? C8 C3 C9 C14 179.72(7) . . . . ? C8 C3 C9 C15 0.69(11) . . . . ? C8 C10 C13 C5 0.82(12) . . . . ? C8 C16 C20 C15 0.50(13) . . . . ? C9 C3 C8 C10 179.94(7) . . . . ? C9 C3 C8 C16 -0.88(11) . . . . ? C9 C15 C20 C16 -0.69(13) . . . . ? C10 C8 C16 C20 179.45(8) . . . . ? C11 C2 C7 C6 -177.34(7) . . . . ? C11 C2 C7 C18 7.07(12) . . . . ? C14 C9 C15 C20 -178.92(8) . . . . ? C15 C9 C14 C11 177.45(8) . . . . ? C16 C8 C10 C13 -177.63(8) . . . . ? C17 C4 C5 C1 176.49(7) . . . . ? C17 C4 C5 C13 -3.85(12) . . . . ? C17 C4 C6 C7 -174.71(7) . . . . ? 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 3.0000 3.0000 5.0000 0.1574 0.3024 0.2888 -5.0000 0.0000 3.0000 -0.2175 -0.4389 0.0792 -1.0000 2.0000 5.0000 -0.0287 -0.0608 0.2357 -1.0000 5.0000 -0.0000 -0.2790 0.0602 0.1859 1.0000 -5.0000 -1.0000 0.2555 -0.0532 -0.2186 2.0000 -9.0000 -21.0000 0.0204 0.0542 -1.0209 3.0000 -1.0000 -5.0000 0.0996 0.2568 -0.1901 6.0000 -6.0000 -20.0000 0.1415 0.4681 -0.8592 10.0000 1.0000 -9.0000 0.3203 0.9275 -0.2186 5.0000 3.0000 1.0000 0.1786 0.4975 0.1655 0.0000 2.0000 5.0000 0.0289 0.0228 0.2394 -2.0000 -4.0000 -5.0000 -0.0555 -0.2476 -0.3229 -3.0000 1.0000 5.0000 -0.0996 -0.2568 0.1901 -1.0000 5.0000 4.0000 -0.1850 0.0324 0.3168 0.0000 -2.0000 5.0000 0.2060 -0.0922 0.0877 -0.0000 2.0000 -24.0000 -0.6523 0.2242 -0.7093