#------------------------------------------------------------------------------ #$Date: 2019-05-18 08:14:21 +0300 (Sat, 18 May 2019) $ #$Revision: 215299 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108396.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2108396 loop_ _publ_author_name 'Tcho\'n, Daniel' 'Makal, Anna' _publ_section_title ; Structure and piezochromism of pyrene-1-carbaldehyde at high pressure ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first ; ; _journal_paper_doi 10.1107/S2052520619003354 _journal_volume 75 _journal_year 2019 _chemical_formula_moiety 'C17 H10 O' _chemical_formula_sum 'C17 H10 O' _chemical_formula_weight 230.25 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2018-06-25 _audit_creation_method ; Olex2 1.2 (compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 109.649(18) _cell_angle_beta 99.384(16) _cell_angle_gamma 100.652(11) _cell_formula_units_Z 2 _cell_length_a 6.6950(8) _cell_length_b 8.1846(11) _cell_length_c 10.306(2) _cell_measurement_reflns_used 1136 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.6970 _cell_measurement_theta_min 1.8700 _cell_volume 506.97(16) _computing_cell_refinement 'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)' _computing_data_collection 'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)' _computing_data_reduction 'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.555 _diffrn_measured_fraction_theta_max 0.381 _diffrn_measurement_details '#__ type_ start__ end____ width___ exp.time_ 1 omega -150.00 -94.00 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - -20.0000 70.0000 -24.2319 280 #__ type_ start__ end____ width___ exp.time_ 2 omega -150.00 -94.00 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - -20.0000 70.0000 155.7681 280 #__ type_ start__ end____ width___ exp.time_ 3 omega -105.00 -76.80 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - 20.0000 70.0000 155.7700 141 #__ type_ start__ end____ width___ exp.time_ 4 omega -105.00 -74.80 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - 20.0000 70.0000 -24.2300 151 #__ type_ start__ end____ width___ exp.time_ 5 omega -96.00 -30.00 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - 20.0000 -70.0000 24.2300 330 #__ type_ start__ end____ width___ exp.time_ 6 omega -103.40 -66.00 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - -20.0000 -70.0000 -155.7700 187 #__ type_ start__ end____ width___ exp.time_ 7 omega -103.40 -66.00 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - -20.0000 -70.0000 24.2300 187 #__ type_ start__ end____ width___ exp.time_ 8 omega -96.00 -30.00 0.2000 0.1970 omega____ theta____ kappa____ phi______ frames - 20.0000 -70.0000 -155.7700 330' _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'dectris-CrysAlisPro-abstract goniometer imported dectris images' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0124369000 _diffrn_orient_matrix_UB_12 -0.0253377000 _diffrn_orient_matrix_UB_13 -0.0514228000 _diffrn_orient_matrix_UB_21 0.0702916000 _diffrn_orient_matrix_UB_22 0.0327455000 _diffrn_orient_matrix_UB_23 0.0034380000 _diffrn_orient_matrix_UB_31 0.0264840000 _diffrn_orient_matrix_UB_32 -0.0504261000 _diffrn_orient_matrix_UB_33 0.0028339000 _diffrn_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.4859 _diffrn_reflns_av_R_equivalents 0.0929 _diffrn_reflns_av_unetI/netI 0.0187 _diffrn_reflns_Laue_measured_fraction_full 0.555 _diffrn_reflns_Laue_measured_fraction_max 0.381 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 1830 _diffrn_reflns_point_group_measured_fraction_full 0.555 _diffrn_reflns_point_group_measured_fraction_max 0.381 _diffrn_reflns_theta_full 16.950 _diffrn_reflns_theta_max 22.708 _diffrn_reflns_theta_min 1.869 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 0.048 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.21550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.' _exptl_crystal_density_diffrn 1.508 _exptl_crystal_description ; ; _exptl_crystal_F_000 240 _refine_diff_density_max 0.551 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.102 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 1830 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.1330 _refine_ls_R_factor_gt 0.0947 _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^)+(0.1271P)^2^+0.3938P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2525 _refine_ls_wR_factor_ref 0.2823 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1190 _reflns_number_total 1830 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file xk5054sup1.cif _cod_data_source_block 10kbar _cod_original_cell_volume 506.95(16) _cod_database_code 2108396 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula 'C17 H10 O1' _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. ; _diffrn_oxdiff_twin_integration_method simultaneous _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.788(4) 0.212(4) 2. Fixed Uiso At 1.2 times of: All C(H) groups 3.a Aromatic/amide H refined with riding coordinates: C4(H4), C11(H11), C13(H13), C3(H3), C14(H14), C10(H10), C6(H6), C17(H17), C8(H8), C7(H7) ; _shelx_res_file ; TITL 3d_twin1_hklf4_a.res in P-1 3d_twin1_hklf4.res created by SHELXL-2016/6 at 18:39:41 on 25-Jun-2018 REM Old TITL 3d_twin1_hklf4 in P-1 REM SHELXT solution in P-1 REM R1 0.357, Rweak 0.005, Alpha 0.149, Orientation as input REM Formula found by SHELXT: C17 O CELL 0.4859 6.695 8.1846 10.3057 109.649 99.384 100.652 ZERR 2 0.0008 0.0011 0.0024 0.018 0.016 0.011 LATT 1 SFAC C H O DISP C 0.001 0.001 6.068 DISP H -0 0 0.607 DISP O 0.004 0.003 13.336 UNIT 34 20 2 L.S. 10 PLAN 20 BOND $H list 4 fmap 2 ACTA OMIT 3 -6 2 OMIT 9 -4 -3 REM REM REM WGHT 0.127100 0.393800 BASF 0.21169 FVAR 8.78270 C2 1 0.711456 0.344745 0.447727 11.00000 0.01644 0.01777 = 0.01637 0.00459 0.00203 0.00454 C12 1 0.799764 0.669910 0.496294 11.00000 0.02281 0.01810 = 0.01613 0.00702 0.00405 0.00705 C15 1 0.756636 0.523504 0.544159 11.00000 0.01962 0.01610 = 0.01433 0.00607 0.00434 0.00609 C5 1 0.721413 0.422541 0.740915 11.00000 0.02523 0.02331 = 0.02894 0.01633 0.00689 0.00746 C9 1 0.805711 0.744567 0.785746 11.00000 0.02415 0.02169 = 0.01262 0.00548 0.00437 0.00676 C4 1 0.679266 0.242541 0.640891 11.00000 0.02957 0.01604 = 0.02217 0.00993 0.00775 0.00554 AFIX 43 H4 2 0.655284 0.148997 0.673094 11.00000 -1.20000 AFIX 0 C11 1 0.845681 0.849636 0.596201 11.00000 0.02859 0.01925 = 0.03889 0.01853 0.01098 0.00888 AFIX 43 H11 2 0.874676 0.943681 0.565017 11.00000 -1.20000 AFIX 0 O1 3 0.593089 -0.014929 0.194262 11.00000 0.07236 0.02461 = 0.05287 0.00484 0.03067 0.00489 C16 1 0.764533 0.566148 0.691381 11.00000 0.01898 0.01891 = 0.02242 0.00951 0.00446 0.00474 C13 1 0.793221 0.630421 0.353089 11.00000 0.02987 0.02514 = 0.02457 0.01422 0.00953 0.00951 AFIX 43 H13 2 0.819398 0.723898 0.320999 11.00000 -1.20000 AFIX 0 C3 1 0.672688 0.202110 0.501385 11.00000 0.02848 0.01923 = 0.02722 0.01223 0.01211 0.00770 AFIX 43 H3 2 0.643312 0.082879 0.439925 11.00000 -1.20000 AFIX 0 C14 1 0.748568 0.454927 0.257368 11.00000 0.03201 0.03243 = 0.01368 0.01250 0.01138 0.00956 AFIX 43 H14 2 0.748355 0.432819 0.162721 11.00000 -1.20000 AFIX 0 C1 1 0.703200 0.308487 0.301235 11.00000 0.02657 0.02337 = 0.00614 0.00385 0.00952 0.01003 C10 1 0.848477 0.887679 0.733653 11.00000 0.03148 0.01645 = 0.02048 0.00626 0.00513 0.00604 AFIX 43 H10 2 0.878044 1.006606 0.795782 11.00000 -1.20000 AFIX 0 C6 1 0.723477 0.463128 0.882327 11.00000 0.04850 0.03352 = 0.01544 0.01856 0.00680 0.00916 AFIX 43 H6 2 0.699537 0.370743 0.915787 11.00000 -1.20000 AFIX 0 C17 1 0.649948 0.133717 0.189423 11.00000 0.03881 0.03495 = 0.02479 0.01268 0.01797 0.01271 AFIX 43 H17 2 0.660150 0.133457 0.100434 11.00000 -1.20000 AFIX 0 C8 1 0.803477 0.781144 0.927751 11.00000 0.03846 0.02380 = 0.02360 0.00357 0.00934 0.01044 AFIX 43 H8 2 0.830323 0.899307 0.990807 11.00000 -1.20000 AFIX 0 C7 1 0.760699 0.639613 0.975639 11.00000 0.05540 0.04079 = 0.01748 0.01605 0.01351 0.01278 AFIX 43 H7 2 0.757314 0.664228 1.070054 11.00000 -1.20000 AFIX 0 HKLF 5 REM 3d_twin1_hklf4_a.res in P-1 REM R1 = 0.0947 for 1190 Fo > 4sig(Fo) and 0.1330 for all 1830 data REM 164 parameters refined using 0 restraints END WGHT 0.1271 0.3937 REM Highest difference peak 0.551, deepest hole -0.388, 1-sigma level 0.102 Q1 1 0.7499 0.5457 0.4814 11.00000 0.05 0.55 Q2 1 0.6831 0.3226 0.2195 11.00000 0.05 0.44 Q3 1 0.7078 0.2850 0.1329 11.00000 0.05 0.44 Q4 1 0.6437 0.1842 0.3345 11.00000 0.05 0.43 Q5 1 0.7307 0.5031 0.4052 11.00000 0.05 0.39 Q6 1 0.8231 0.6491 0.5763 11.00000 0.05 0.39 Q7 1 0.8412 0.8321 0.4761 11.00000 0.05 0.38 Q8 1 0.7527 0.4269 0.3214 11.00000 0.05 0.38 Q9 1 0.6413 0.2374 0.4257 11.00000 0.05 0.38 Q10 1 0.8319 0.6833 0.3156 11.00000 0.05 0.37 Q11 1 0.7058 0.4635 0.6808 11.00000 0.05 0.37 Q12 1 0.8785 0.8472 0.7988 11.00000 0.05 0.36 Q13 1 0.8264 0.7241 0.4615 11.00000 0.05 0.36 Q14 1 0.7069 0.3056 0.4968 11.00000 0.05 0.36 Q15 1 0.7456 0.6629 0.9166 11.00000 0.05 0.35 Q16 1 0.7270 0.6927 0.4946 11.00000 0.05 0.34 Q17 1 0.6951 0.4131 0.5969 11.00000 0.05 0.34 Q18 1 0.7879 0.6482 0.3077 11.00000 0.05 0.34 Q19 1 0.6346 0.0912 0.2410 11.00000 0.05 0.34 Q20 1 0.7514 0.5158 0.7343 11.00000 0.05 0.34 ; _shelx_res_checksum 70789 _shelx_hkl_file ; 0 -1 1 125889. 114.090 1 0 1 0 80868.7 94.5796 1 0 -2 2 23174.0 72.2144 1 0 -2 1 68743.6 100.279 1 0 -2 0 658.149 12.6646 1 0 3 -3 3217.08 49.3973 1 0 3 -2 27357.6 57.8954 1 0 -3 1 1477.43 16.1056 1 0 -3 0 72.3562 22.7405 1 0 -4 4 109.250 24.3919 1 0 -4 3 20155.9 60.9067 1 0 4 -2 3743.62 16.4191 1 0 -4 1 758.541 18.3227 1 0 -4 0 16.1154 19.1909 1 0 -5 5 3945.57 61.1870 1 0 -5 4 1229.46 23.7931 1 0 5 -3 3079.96 24.6625 1 0 -5 2 51.4297 10.1858 1 0 -5 1 21.0449 18.6977 1 0 -5 0 528.146 29.5614 1 0 -6 6 1646.40 78.5794 1 0 -6 5 748.002 42.3036 1 0 -6 4 1581.42 42.5882 1 0 -6 3 28.8896 25.4997 1 0 6 -2 43985.7 130.150 1 0 -6 1 35425.1 145.597 1 0 -6 0 1697.31 46.6876 1 0 -7 6 4335.78 78.1211 1 0 -7 5 1394.21 52.4856 1 0 -7 4 842.315 45.5396 1 0 -7 3 1719.82 41.0184 1 0 7 -2 81172.6 194.847 1 0 -7 1 544.658 43.6825 1 0 -8 7 5741.04 108.128 1 0 8 -4 1829.76 105.888 1 0 8 -1-27.9831 54.0617 1 0 9 -7 218.071 65.8364 1 0 9 -6 52.2621 59.7925 1 0 9 -5 1536.72 54.7642 1 0 -9 4 368.010 47.3201 1 0 -9 3 667.397 46.3600 1 0 9 -2 69.2171 45.9906 1 0 -9 1 356.311 65.7743 1 0 -10 8 122.715 80.0016 1 0 -10 7 71.0921 76.7855 1 0 -10 6-31.7372 57.6113 1 0 -10 5 6311.94 88.7443 1 0 -10 4 6485.96 87.2131 1 0 10 -3 86.2465 56.2879 1 0 10 -2-4.11307 75.8223 1 0 -11 8 306.622 144.484 1 0 11 -7 128.164 69.6452 1 0 -11 6 70.2673 66.0652 1 0 -11 5 615.960 66.7946 1 0 11 -4 1154.73 79.7399 1 -9 0 5 1084.64 187.348 -2 0 -11 4 1084.64 187.348 1 0 -11 3 153.271 67.6360 1 0 -11 2 92.5424 97.7571 1 0 12 -8 303.634 158.141 1 0 -12 7 222.332 102.969 1 0 12 -6 88.0748 76.9344 1 0 12 -5 294.682 80.0104 1 0 -12 4 747.046 102.826 1 1 -12 3 873.427 81.7437 1 -1 12 -4 31.4959 74.6500 1 -1 12 -5 183.546 69.7020 1 -1 12 -6 33.1785 73.1001 1 1 -12 7 267.827 78.1271 1 -1 12 -8-16.9686 83.9323 1 -1 11 -2 783.641 68.2239 1 1 -11 3 393.442 63.4818 1 -1 11 -4 77.0235 60.3741 1 -1 11 -5 1296.78 67.5089 1 -1 11 -6 544.589 67.1751 1 1 -11 7 90.8064 67.2019 1 -1 11 -8 182.297 94.0120 1 -1 10 -2 197.436 53.2610 1 -1 10 -3 28.5747 51.1192 1 1 -10 4 259.832 50.5063 1 -1 10 -5 7306.08 89.3010 1 -1 10 -6 517.474 58.1715 1 1 -10 7 103.214 73.6674 1 1 -10 8 106.685 99.2358 1 1 -9 1 441.649 58.0370 1 1 -9 2-26.4322 41.6956 1 -1 9 -3 353.940 42.7832 1 1 -9 4 107.665 41.9970 1 -1 9 -5 144.328 43.5269 1 1 -9 6 115.439 56.7613 1 1 -9 7 75.6205 63.5689 1 1 -8 1 1211.90 104.049 1 1 -8 2 61.4036 37.6500 1 -1 8 -3 7.41792 33.3510 1 -1 8 -4 2817.92 53.7931 1 1 -8 5 1123.07 58.1973 1 -1 8 -6 1111.57 82.4548 1 1 -7 0 1664.20 93.0870 1 -1 7 -1 11540.6 93.4191 1 1 -7 2 35064.0 125.353 1 1 -7 3 374.589 31.1653 1 -1 7 -4 2136.48 51.3027 1 -1 7 -5 220.507 40.5911 1 1 -7 6 4613.27 79.2306 1 1 -6 0 176.868 33.5418 1 1 -6 1 43512.7 151.340 1 -1 6 -2 39.0326 18.2745 1 -1 6 -3 41.3495 17.5490 1 1 -6 4 3054.77 51.1118 1 1 -6 5 151.530 25.3398 1 1 -5 0 7857.59 63.2240 1 1 -5 1 2742.58 30.7242 1 -1 5 -2 1255.95 14.9578 1 -1 5 -3 1181.54 15.7846 1 1 -5 4 15482.7 92.8117 1 1 -4 0 29.9329 15.4463 1 1 -4 1 152.191 11.4667 1 -1 4 -2 2305.33 17.8071 1 1 -4 3 87858.3 113.372 1 1 -4 4 24150.0 162.808 1 1 -3 0 632.878 13.9977 1 1 -3 1 20.7664 6.32942 1 1 -3 2 405.815 9.14100 1 1 -3 3 56095.8 216.542 1 -1 2 0 2364.97 16.2098 1 1 -2 1 265.448 6.55634 1 -1 2 -2 11674.2 98.9039 1 1 -1 0 313.165 7.59504 1 1 -1 1 47054.1 91.0945 1 -1 0 0 4518.67 22.2721 1 1 1 -1 22373.4 50.4529 1 1 1 0 13022.0 49.7592 1 -1 -2 2 1028.19 17.4861 1 -1 -2 1 7863.76 39.9936 1 -1 -2 0 4895.53 33.2581 1 1 3 0 4842.74 51.7144 1 -1 -4 4 33610.5 129.239 1 -1 -4 3 33626.5 114.973 1 -1 -4 2 5140.35 40.1874 1 -1 -4 1 893.220 25.9822 1 -1 -4 0 12995.6 76.8797 1 -1 -5 5 21.9707 31.0398 1 1 5 -4 179.985 27.3694 1 -1 -5 3 9865.28 71.0580 1 1 5 -2 2677.51 35.6048 1 1 5 -1 6093.44 59.6874 1 1 5 0-0.31260 27.5537 1 1 6 -6 264.527 41.7195 1 1 6 -5 1651.43 49.9062 1 -1 -6 4 376.500 36.4882 1 1 6 -3 3256.85 45.2970 1 1 6 -2 21898.1 97.2649 1 1 6 -1 59918.1 196.651 1 -1 -7 7 144.177 162.525 1 -1 -7 6 6286.67 88.0169 1 -1 -7 5 3636.90 67.8442 1 -1 -7 4 91.0561 34.0764 1 1 7 -3 868.434 37.6762 1 -1 -7 2 6563.65 65.5589 1 1 7 -1 167.366 43.7764 1 -1 -8 7 160.559 59.7810 1 1 8 -6 130.637 54.1131 1 1 8 -5 8.91552 57.2299 1 1 8 -4 703.815 62.1290 1 1 8 -3 1448.09 52.5398 1 -1 -8 2 168.075 41.8678 1 1 8 -1 699.723 58.1292 1 -1 -9 8 81.5931 69.4584 1 1 9 -7 177.576 71.3521 1 -1 -9 6-1.03501 64.5266 1 1 9 -5 4831.67 76.4580 1 1 9 -4 738.014 50.8519 1 -1 -9 3 130.887 48.7153 1 -1 -9 2 8.24062 48.7112 1 1 10 -8 257.419 87.5269 1 -1 -10 7 158.717 79.6850 1 1 10 -6 462.928 61.7324 1 1 10 -5 4439.62 84.0551 1 -1 -10 4 111.179 53.6968 1 -1 -10 3 15.7777 56.1351 1 -1 -10 2 19.0959 59.8743 1 -1 -11 9 919.044 143.094 1 -1 -11 8 186.569 81.9010 1 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0 -6 23.8416 41.9491 2 7 0 -5 48.0879 41.8638 2 7 0 -4 37.0259 40.5381 2 7 0 -3 11.7339 40.3903 2 -7 0 2 64.6243 40.7103 2 -7 0 1 38.2196 40.4016 2 7 0 0 5.60843 40.2896 2 7 0 1 45.2038 41.1154 2 7 0 2 283.038 44.0572 2 7 0 3 120.772 43.1483 2 7 1 -9 6.93778 57.8875 2 7 1 -8-22.7541 42.4151 2 -7 -1 7 219.250 52.3206 2 7 1 -6 29.7688 41.2142 2 7 1 -5 7.99123 40.2508 2 7 1 -4-7.16297 39.7136 2 -7 -1 3 1060.98 54.4747 2 -7 -1 2 493.321 50.2330 2 -7 -1 1-17.5957 46.4430 2 -7 -1 0-7.27368 46.2675 2 -7 -1 -1 318.552 93.2634 2 -7 -1 -2 300.427 93.7073 2 -7 -2 9 125.208 53.4171 2 -7 -2 8 2545.93 98.4103 2 -7 -2 7 2637.40 94.9982 2 -7 -2 6 232.612 69.1061 2 -8 4 5 330.966 98.3277 2 8 -4 -4 75.3742 70.3412 2 8 -4 -3-30.4888 63.1059 2 8 -4 -2 101.399 62.2126 2 -8 4 1 100.629 62.9612 2 8 -4 0 155.667 62.6446 2 8 -4 1 137.520 61.3400 2 8 -4 2 103.636 65.6784 2 8 -4 3-68.4923 63.9197 2 -8 4 -4-67.7862 67.1099 2 8 -3 -7-33.4278 71.0929 2 -8 3 6 16.5028 65.6411 2 8 -3 -5 57.5553 65.4315 2 8 -3 -4 152.666 63.0122 2 -8 3 3 196.643 69.2133 2 -8 3 2 115.837 64.1248 2 8 -3 -1 135.713 60.5429 2 8 -3 0 819.259 66.4512 2 -8 3 -1 2726.83 65.3946 2 8 -3 2 130.145 53.1499 2 8 -3 3 143.191 52.0473 2 -8 2 8 90.8650 56.8880 2 8 -2 -7 245.430 56.0749 2 8 -2 -6 54.2364 52.4385 2 8 -2 -5 115.574 53.2644 2 -8 2 4 1606.45 61.0428 2 8 -2 -3-1.63496 50.7107 2 -8 2 2 80.2144 51.5173 2 -8 2 1 726.363 53.6704 2 -8 2 0 7465.71 81.8611 2 -8 2 -1 1851.51 59.0982 2 -8 2 -3 23.9700 52.8474 2 8 -1 -8 164.198 61.6773 2 -8 1 7 39.8484 54.5624 2 8 -1 -6 59.2696 53.5366 2 -8 1 5 1482.42 60.2152 2 -8 1 4 611.243 56.1873 2 -8 1 3 103.670 51.7427 2 8 -1 -2 38.5491 50.7551 2 -8 1 1 114.957 50.5827 2 8 -1 0 529.124 52.8782 2 8 -1 1 8.70842 50.3109 2 8 -1 2 25.8527 51.3471 2 8 -1 3 60.2966 52.6137 2 8 0 -9 157.753 69.7031 2 8 0 -8 55.7127 57.1181 2 8 0 -7 26.1123 52.3646 2 8 0 -6 68.1143 53.4898 2 8 0 -5-2.43767 51.6344 2 8 0 -4-59.5173 50.8145 2 8 0 -3 5.71440 50.5827 2 8 0 -2-11.3052 50.4972 2 8 0 -1 160.095 50.2517 2 8 0 0 68.1232 51.6912 2 8 0 1-21.4520 50.0107 2 8 0 2 46.1831 52.7071 2 8 1 -9 123.580 54.5582 2 8 1 -8 0.48054 57.8776 2 8 1 -7 38.5241 52.2875 2 8 1 -6 15.3651 50.5775 2 8 1 -5 28.0608 53.2364 2 8 1 -4-13.7986 50.0241 2 8 1 -3 56.2211 50.7036 2 8 1 -2 246.264 51.8796 2 8 1 -1-58.0711 49.0439 2 8 1 0 23.7497 70.5824 2 8 1 1 5.04621 74.9416 2 8 2 -9 38.8282 63.1342 2 -9 4 6 1327.11 143.580 2 -9 4 5-124.636 120.650 2 9 -4 -4-106.716 79.3065 2 9 -4 -3-56.6391 77.8627 2 9 -4 -2-53.6953 76.7424 2 9 -4 0 131.211 78.3069 2 9 -4 1 119.992 79.5081 2 9 -4 2 41.2050 81.5884 2 9 -4 3 59.0986 61.9506 2 9 -3 -8-50.1384 67.6989 2 9 -3 -7 53.2091 68.8705 2 9 -3 -6 113.885 68.1250 2 9 -3 -5 120.990 69.3792 2 -9 3 4 201.375 67.8893 2 9 -3 -3 280.081 66.9396 2 9 -3 -2 163.658 64.0328 2 9 -3 -1 212.456 62.6949 2 9 -3 0 165.153 60.4982 2 9 -3 1 185.005 62.0392 2 -9 3 -2 133.108 65.7368 2 9 -3 3 129.582 66.1445 2 9 -2 -8 234.453 72.8447 2 9 -2 -7 95.6003 67.9271 2 9 -2 -6 114.037 66.3199 2 9 -2 -5 60.6454 63.9894 2 9 -2 -4 6.61407 65.4000 2 9 -2 -3-15.0917 64.4204 2 9 -2 -2-45.4544 65.3746 2 9 -2 -1 55.6408 65.9568 2 9 -2 0 24.7900 63.7421 2 9 -2 1 390.715 66.4606 2 9 -2 2 69.9159 65.6735 2 -9 2 -3 12.2836 119.246 2 9 -1 -9 90.1547 147.455 2 9 -1 -8 33.0748 67.9708 2 9 -1 -7 51.4250 67.5795 2 -9 1 6 53.2900 65.6758 2 -9 1 5 72.5312 64.8018 2 9 -1 -4 114.663 64.9913 2 -9 1 3 142.975 64.3824 2 -9 1 2 102.370 63.8590 2 9 -1 -1 118.621 63.6969 2 9 -1 0 106.593 63.9626 2 -9 1 -1 156.267 67.4174 2 9 -1 2 27.4748 62.7883 2 -9 0 9 19.7115 64.8056 2 9 0 -8 66.0290 67.1952 2 9 0 -7 62.8927 65.8868 2 9 0 -6 8.37343 63.8188 2 9 0 -5-1.55835 73.5313 2 9 0 -4-12.8852 62.7536 2 9 0 -3 67.1426 62.8777 2 9 0 -2 105.466 63.1157 2 9 0 -1-25.7040 63.1465 2 9 0 0-46.3145 65.6333 2 9 0 1-0.62555 63.0565 2 9 0 2 399.235 64.0100 2 9 1 -9 49.6878 63.4815 2 9 1 -8 248.769 65.6847 2 -9 -1 7 949.625 70.5941 2 9 1 -5 42.1395 66.0614 2 9 1 -4 66.6933 63.6761 2 -9 -1 3 979.072 68.4667 2 9 1 -2 188.207 65.2967 2 9 1 -1 15.4790 84.8987 2 10 -4 -1 192.590 138.649 2 10 -4 0 227.561 141.418 2 10 -4 1 263.907 144.441 2 10 -4 2-38.7057 145.279 2 10 -4 3-236.649 147.500 2 10 -3 -4 446.500 123.904 2 10 -3 -3 343.331 94.6020 2 10 -3 -2 484.663 131.827 2 10 -3 -1 692.760 135.525 2 -10 3 0 2606.26 151.206 2 -10 3 -1 2118.73 151.607 2 -10 3 -2 343.686 89.6134 2 10 -2 -5 408.659 112.915 2 10 -2 -4 412.069 115.830 2 10 -2 -3-156.420 121.149 2 10 -2 -2 43.4188 95.1133 2 10 -2 -1 216.923 97.4233 2 10 -2 0 927.358 132.324 2 10 -2 1 136.643 101.517 2 10 -2 2-26.1137 82.2000 2 10 -1 -4 143.583 109.428 2 -10 1 3-12.9568 109.890 2 10 -1 -2 175.856 111.823 2 -10 1 1 84.3455 114.949 2 -10 1 0 27.3997 116.862 2 10 -1 1 210.573 151.542 2 ; _shelx_hkl_checksum 98076 _olex2_submission_special_instructions 'No special instructions were received' 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 C2 C 0.7115(5) 0.3447(5) 0.4477(6) 0.0176(10) Uani 1 1 d . C12 C 0.7998(5) 0.6699(6) 0.4963(7) 0.0187(10) Uani 1 1 d . C15 C 0.7566(5) 0.5235(5) 0.5442(6) 0.0164(10) Uani 1 1 d . C5 C 0.7214(5) 0.4225(6) 0.7409(7) 0.0239(13) Uani 1 1 d . C9 C 0.8057(6) 0.7446(6) 0.7857(6) 0.0197(10) Uani 1 1 d . C4 C 0.6793(6) 0.2425(6) 0.6409(7) 0.0217(11) Uani 1 1 d . H4 H 0.655284 0.148997 0.673094 0.026 Uiso 1 1 calc R C11 C 0.8457(6) 0.8496(6) 0.5962(8) 0.0261(14) Uani 1 1 d . H11 H 0.874676 0.943681 0.565017 0.031 Uiso 1 1 calc R O1 O 0.5931(5) -0.0149(5) 0.1943(6) 0.0517(14) Uani 1 1 d . C16 C 0.7645(5) 0.5661(6) 0.6914(7) 0.0197(12) Uani 1 1 d . C13 C 0.7932(6) 0.6304(6) 0.3531(7) 0.0245(12) Uani 1 1 d . H13 H 0.819398 0.723898 0.320999 0.029 Uiso 1 1 calc R C3 C 0.6727(6) 0.2021(6) 0.5014(7) 0.0232(12) Uani 1 1 d . H3 H 0.643312 0.082879 0.439925 0.028 Uiso 1 1 calc R C14 C 0.7486(5) 0.4549(6) 0.2574(6) 0.0241(10) Uani 1 1 d . H14 H 0.748355 0.432819 0.162721 0.029 Uiso 1 1 calc R C1 C 0.7032(5) 0.3085(6) 0.3012(6) 0.0180(9) Uani 1 1 d . C10 C 0.8485(6) 0.8877(6) 0.7337(7) 0.0232(12) Uani 1 1 d . H10 H 0.878044 1.006606 0.795782 0.028 Uiso 1 1 calc R C6 C 0.7235(7) 0.4631(7) 0.8823(7) 0.0303(12) Uani 1 1 d . H6 H 0.699537 0.370743 0.915787 0.036 Uiso 1 1 calc R C17 C 0.6499(6) 0.1337(6) 0.1894(7) 0.0307(13) Uani 1 1 d . H17 H 0.660150 0.133457 0.100434 0.037 Uiso 1 1 calc R C8 C 0.8035(6) 0.7811(7) 0.9278(7) 0.0295(13) Uani 1 1 d . H8 H 0.830323 0.899307 0.990807 0.035 Uiso 1 1 calc R C7 C 0.7607(7) 0.6396(7) 0.9756(7) 0.0359(13) Uani 1 1 d . H7 H 0.757314 0.664228 1.070054 0.043 Uiso 1 1 calc R 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 C2 0.0164(14) 0.018(3) 0.016(3) 0.005(3) 0.002(2) 0.0045(15) C12 0.0228(16) 0.018(3) 0.016(3) 0.007(3) 0.004(2) 0.0071(16) C15 0.0196(15) 0.016(3) 0.014(3) 0.006(3) 0.004(2) 0.0061(16) C5 0.0252(17) 0.023(3) 0.029(4) 0.016(4) 0.007(3) 0.0075(17) C9 0.0242(16) 0.022(3) 0.013(3) 0.005(3) 0.004(2) 0.0068(17) C4 0.0296(18) 0.016(2) 0.022(3) 0.010(3) 0.008(3) 0.0055(17) C11 0.0286(18) 0.019(3) 0.039(4) 0.019(4) 0.011(3) 0.0089(17) O1 0.072(2) 0.025(2) 0.053(4) 0.005(3) 0.031(3) 0.0049(17) C16 0.0190(15) 0.019(3) 0.022(3) 0.010(4) 0.004(2) 0.0047(16) C13 0.0299(18) 0.025(3) 0.025(3) 0.014(4) 0.010(3) 0.0095(18) C3 0.0285(18) 0.019(3) 0.027(4) 0.012(4) 0.012(3) 0.0077(17) C14 0.0320(18) 0.032(3) 0.014(3) 0.013(3) 0.011(2) 0.0096(18) C1 0.0266(17) 0.023(3) 0.006(2) 0.004(3) 0.010(2) 0.0100(17) C10 0.0315(18) 0.016(3) 0.020(3) 0.006(3) 0.005(3) 0.0060(17) C6 0.049(2) 0.034(3) 0.015(3) 0.019(4) 0.007(3) 0.009(2) C17 0.039(2) 0.035(3) 0.025(3) 0.013(4) 0.018(3) 0.013(2) C8 0.038(2) 0.024(3) 0.024(4) 0.004(4) 0.009(3) 0.010(2) C7 0.055(3) 0.041(3) 0.017(3) 0.016(4) 0.014(3) 0.013(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0010 0.0010 '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 0.0040 0.0030 '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 C15 C2 C3 118.3(5) C15 C2 C1 119.7(4) C1 C2 C3 122.0(5) C11 C12 C15 119.2(5) C13 C12 C15 118.6(5) C13 C12 C11 122.1(4) C2 C15 C12 120.3(5) C2 C15 C16 121.7(4) C16 C15 C12 118.0(4) C4 C5 C16 118.2(5) C6 C5 C4 122.8(4) C6 C5 C16 119.0(5) C16 C9 C10 119.2(5) C8 C9 C16 119.6(4) C8 C9 C10 121.2(5) C5 C4 H4 118.5 C3 C4 C5 122.9(4) C3 C4 H4 118.5 C12 C11 H11 118.9 C10 C11 C12 122.2(4) C10 C11 H11 118.9 C15 C16 C5 118.8(5) C9 C16 C15 121.1(4) C9 C16 C5 120.1(5) C12 C13 H13 119.3 C14 C13 C12 121.4(4) C14 C13 H13 119.3 C2 C3 H3 120.0 C4 C3 C2 120.0(5) C4 C3 H3 120.0 C13 C14 H14 119.5 C13 C14 C1 121.1(5) C1 C14 H14 119.5 C2 C1 C17 126.1(4) C14 C1 C2 118.8(4) C14 C1 C17 115.1(5) C9 C10 H10 119.9 C11 C10 C9 120.3(5) C11 C10 H10 119.9 C5 C6 H6 119.4 C5 C6 C7 121.1(4) C7 C6 H6 119.4 O1 C17 C1 129.5(6) O1 C17 H17 115.3 C1 C17 H17 115.3 C9 C8 H8 120.0 C9 C8 C7 120.1(5) C7 C8 H8 120.0 C6 C7 C8 120.2(5) C6 C7 H7 119.9 C8 C7 H7 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C2 C15 1.407(7) C2 C3 1.451(5) C2 C1 1.427(8) C12 C15 1.442(5) C12 C11 1.425(7) C12 C13 1.392(9) C15 C16 1.427(8) C5 C4 1.429(7) C5 C16 1.432(5) C5 C6 1.379(9) C9 C16 1.401(7) C9 C10 1.446(5) C9 C8 1.395(9) C4 H4 0.9300 C4 C3 1.354(9) C11 H11 0.9300 C11 C10 1.340(9) O1 C17 1.226(5) C13 H13 0.9300 C13 C14 1.385(7) C3 H3 0.9300 C14 H14 0.9300 C14 C1 1.417(5) C1 C17 1.439(7) C10 H10 0.9300 C6 H6 0.9300 C6 C7 1.389(7) C17 H17 0.9300 C8 H8 0.9300 C8 C7 1.405(6) C7 H7 0.9300 loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.7601 3031 29 2 0.2399 2911 29 loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.788(4) 2 0.212(4) _cod_database_fobs_code 2108396