#------------------------------------------------------------------------------ #$Date: 2019-05-18 08:14:21 +0300 (Sat, 18 May 2019) $ #$Revision: 215299 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108399.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_2108399 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 109.37(3) _cell_angle_beta 99.57(3) _cell_angle_gamma 100.71(3) _cell_formula_units_Z 2 _cell_length_a 6.477(2) _cell_length_b 8.041(2) _cell_length_c 10.205(3) _cell_measurement_reflns_used 460 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.6140 _cell_measurement_theta_min 1.9140 _cell_volume 477.6(3) _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 0.718 _diffrn_measured_fraction_theta_max 0.520 _diffrn_measurement_details '#__ type_ start__ end____ width___ exp.time_ 1 omega -150.00 -94.00 0.2000 0.3970 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 0.3970 omega____ theta____ kappa____ phi______ frames - -20.0000 70.0000 155.7681 280 #__ type_ start__ end____ width___ exp.time_ 3 omega -105.00 -76.00 0.2000 0.3970 omega____ theta____ kappa____ phi______ frames - 20.0000 70.0000 155.7700 145 #__ type_ start__ end____ width___ exp.time_ 4 omega -105.00 -75.00 0.2000 0.3970 omega____ theta____ kappa____ phi______ frames - 20.0000 70.0000 -24.2300 150 #__ type_ start__ end____ width___ exp.time_ 5 omega -96.00 -30.00 0.2000 0.3970 omega____ theta____ kappa____ phi______ frames - 20.0000 -70.0000 24.2300 330 #__ type_ start__ end____ width___ exp.time_ 6 omega -103.00 -66.00 0.2000 0.3970 omega____ theta____ kappa____ phi______ frames - -20.0000 -70.0000 -155.7700 185 #__ type_ start__ end____ width___ exp.time_ 7 omega -103.80 -66.00 0.2000 0.3970 omega____ theta____ kappa____ phi______ frames - -20.0000 -70.0000 24.2300 189 #__ type_ start__ end____ width___ exp.time_ 8 omega -96.00 -30.00 0.2000 0.3970 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 -0.0506264000 _diffrn_orient_matrix_UB_12 0.0235626000 _diffrn_orient_matrix_UB_13 -0.0250498000 _diffrn_orient_matrix_UB_21 0.0590807000 _diffrn_orient_matrix_UB_22 0.0320340000 _diffrn_orient_matrix_UB_23 -0.0134875000 _diffrn_orient_matrix_UB_31 -0.0123243000 _diffrn_orient_matrix_UB_32 -0.0530677000 _diffrn_orient_matrix_UB_33 -0.0436105000 _diffrn_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.4859 _diffrn_reflns_av_R_equivalents 0.1391 _diffrn_reflns_av_unetI/netI 0.0786 _diffrn_reflns_Laue_measured_fraction_full 0.718 _diffrn_reflns_Laue_measured_fraction_max 0.520 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _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 2461 _diffrn_reflns_point_group_measured_fraction_full 0.718 _diffrn_reflns_point_group_measured_fraction_max 0.520 _diffrn_reflns_theta_full 16.950 _diffrn_reflns_theta_max 22.567 _diffrn_reflns_theta_min 1.900 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 0.051 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.07393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.601 _exptl_crystal_description ; ; _exptl_crystal_F_000 240 _refine_diff_density_max 0.875 _refine_diff_density_min -0.777 _refine_diff_density_rms 0.209 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2461 _refine_ls_number_restraints 162 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.2634 _refine_ls_R_factor_gt 0.1689 _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^)+(0.1308P)^2^+1.3113P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3776 _refine_ls_wR_factor_ref 0.4342 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1176 _reflns_number_total 2461 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file xk5054sup1.cif _cod_data_source_block 28kbar _cod_original_cell_volume 477.5(3) _cod_database_code 2108399 _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: 0.725(6) 0.237(6) 0.0377(16) 2. Fixed Uiso At 1.2 times of: All C(H) groups 3. Uiso/Uaniso restraints and constraints Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 4. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5.a Aromatic/amide H refined with riding coordinates: C3(H3), C14(H14), C8(H8), C6(H6), C7(H7), C4(H4), C13(H13), C11(H11), C17(H17), C10(H10) ; _shelx_res_file ; TITL 3d_twin1_hklf4_a.res in P-1 3d_twin1_hklf4.res created by SHELXL-2016/6 at 18:34:45 on 25-Jun-2018 REM Old TITL 3d_twin1_hklf4 in P-1 REM SHELXT solution in P-1 REM R1 0.245, Rweak 0.024, Alpha 0.174, Orientation as input REM Formula found by SHELXT: C17 O CELL 0.4859 6.4766 8.0414 10.2048 109.366 99.574 100.715 ZERR 2 0.0023 0.0022 0.003 0.025 0.026 0.026 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 RIGU ISOR 0.005 0.01 C12 L.S. 5 PLAN 20 BOND $H list 4 fmap 2 acta OMIT -4 0 1 OMIT -9 7 3 OMIT 2 7 -3 OMIT -5 11 -6 REM REM REM WGHT 0.130800 1.311300 BASF 0.23692 0.03774 FVAR 18.40933 O1 3 0.412329 1.019483 0.810562 11.00000 0.09094 0.01727 = 0.03627 0.00103 0.02857 0.00249 C15 1 0.238559 0.473907 0.456659 11.00000 0.03889 0.01213 = 0.02229 0.00426 0.01212 0.00212 C2 1 0.292229 0.659876 0.555519 11.00000 0.03544 0.01314 = 0.02363 0.00778 0.01062 0.00437 C3 1 0.327002 0.800363 0.498225 11.00000 0.03846 0.01704 = 0.02569 0.01103 0.01132 0.00229 AFIX 43 H3 2 0.352128 0.921479 0.558694 11.00000 -1.20000 AFIX 0 C14 1 0.249526 0.544711 0.744428 11.00000 0.05826 0.02435 = 0.03074 0.00816 0.02325 0.00441 AFIX 43 H14 2 0.247617 0.567838 0.839700 11.00000 -1.20000 AFIX 0 C1 1 0.297072 0.689275 0.701522 11.00000 0.04006 0.01788 = 0.02732 0.00816 0.01908 0.00877 C12 1 0.197311 0.327520 0.504643 11.00000 0.01799 0.02192 = 0.02099 0.01193 0.00006 0.00860 C9 1 0.192503 0.250098 0.213218 11.00000 0.03413 0.02475 = 0.02364 0.00990 0.00828 0.00740 C8 1 0.196281 0.215360 0.069464 11.00000 0.04494 0.02170 = 0.02531 0.00861 0.01479 0.00773 AFIX 43 H8 2 0.173563 0.095818 0.006498 11.00000 -1.20000 AFIX 0 C5 1 0.275830 0.577429 0.257535 11.00000 0.04577 0.01661 = 0.02623 0.00614 0.01799 0.00450 C6 1 0.276947 0.536580 0.113508 11.00000 0.05287 0.02807 = 0.02595 0.01295 0.01132 0.00766 AFIX 43 H6 2 0.307239 0.631026 0.080507 11.00000 -1.20000 AFIX 0 C7 1 0.233822 0.358367 0.019534 11.00000 0.05454 0.03657 = 0.00887 0.00900 0.00441 0.01107 AFIX 43 H7 2 0.229641 0.333058 -0.076795 11.00000 -1.20000 AFIX 0 C4 1 0.324081 0.760594 0.357673 11.00000 0.05000 0.01701 = 0.02984 0.01034 0.02107 0.00307 AFIX 43 H4 2 0.354545 0.855918 0.325630 11.00000 -1.20000 AFIX 0 C16 1 0.236992 0.431809 0.309868 11.00000 0.03657 0.01740 = 0.02224 0.00775 0.00956 0.00588 C13 1 0.204350 0.365552 0.650035 11.00000 0.02911 0.02128 = 0.02351 0.01850 0.00301 0.01352 AFIX 43 H13 2 0.178723 0.270620 0.682972 11.00000 -1.20000 AFIX 0 C11 1 0.147972 0.143397 0.403301 11.00000 0.04303 0.01152 = 0.03487 0.01693 0.01487 0.00773 AFIX 43 H11 2 0.116643 0.047136 0.434229 11.00000 -1.20000 AFIX 0 C17 1 0.355844 0.869855 0.817114 11.00000 0.06830 0.01721 = 0.02943 0.00368 0.02785 0.00951 AFIX 43 H17 2 0.349050 0.870074 0.907486 11.00000 -1.20000 AFIX 0 C10 1 0.146128 0.107047 0.263572 11.00000 0.06468 0.01434 = 0.03148 0.00743 0.02154 0.00909 AFIX 43 H10 2 0.113970 -0.013419 0.200166 11.00000 -1.20000 AFIX 0 HKLF 5 REM 3d_twin1_hklf4_a.res in P-1 REM R1 = 0.1689 for 1176 Fo > 4sig(Fo) and 0.2634 for all 2461 data REM 165 parameters refined using 162 restraints END WGHT 0.1306 1.3121 REM Highest difference peak 0.875, deepest hole -0.777, 1-sigma level 0.209 Q1 1 0.2733 0.6807 0.6165 11.00000 0.05 0.88 Q2 1 0.2660 0.6415 0.2810 11.00000 0.05 0.85 Q3 1 0.2576 0.6168 0.7210 11.00000 0.05 0.80 Q4 1 0.3675 0.7596 0.7835 11.00000 0.05 0.74 Q5 1 -0.0293 0.3438 0.5975 11.00000 0.05 0.74 Q6 1 0.2055 1.0620 0.7196 11.00000 0.05 0.74 Q7 1 0.1243 0.7394 0.2221 11.00000 0.05 0.69 Q8 1 0.4231 0.3229 0.1238 11.00000 0.05 0.68 Q9 1 0.0567 0.3608 -0.0912 11.00000 0.05 0.67 Q10 1 0.3382 0.3843 -0.0054 11.00000 0.05 0.67 Q11 1 0.3638 0.6245 0.1237 11.00000 0.05 0.67 Q12 1 0.3035 0.6429 0.4615 11.00000 0.05 0.67 Q13 1 -0.0111 0.2445 -0.1035 11.00000 0.05 0.66 Q14 1 0.4934 1.0236 0.7791 11.00000 0.05 0.65 Q15 1 0.3128 0.6008 0.4217 11.00000 0.05 0.65 Q16 1 0.2646 0.3035 0.0740 11.00000 0.05 0.64 Q17 1 0.1352 0.6341 0.5277 11.00000 0.05 0.64 Q18 1 0.3034 0.7758 0.7215 11.00000 0.05 0.64 Q19 1 0.3126 0.1354 0.4007 11.00000 0.05 0.63 Q20 1 0.0856 0.7154 0.9443 11.00000 0.05 0.63 ; _shelx_res_checksum 60897 _shelx_hkl_file ; 0 0 -2 63596.1 295.901 1 0 -1 0 355244. 488.965 1 0 -1 -1 48785.2 135.582 1 0 1 2 77337.5 229.995 1 0 1 3 55544.1 235.542 1 0 -1 -4-13.8302 241.958 1 0 1 5 790.769 319.306 1 0 -1 -6 4413.14 436.759 1 0 -1 -7 28174.9 867.624 1 0 2 0 1535.60 143.108 1 0 -2 -1 1502.07 199.249 1 0 -2 -2 172447. 386.223 1 0 -2 -3 41368.1 322.884 1 0 2 4 2015.84 262.624 1 0 2 5 7876.61 363.190 1 0 2 6 25998.4 363.412 1 0 -2 -7 78256.4 840.455 1 0 -2 -8 476.720 802.447 1 0 3 1 1118.57 201.887 1 0 -3 -2 101537. 341.940 1 0 -3 -3 724.638 290.308 1 0 -3 -4 4090.03 244.391 1 0 -3 -5 4760.88 295.259 1 0 -3 -6 38002.1 395.559 1 0 -3 -7 1125.68 375.128 1 0 -3 -8 11280.5 853.145 1 0 -4 0 887.380 321.565 1 0 -4 -1 10955.8 402.234 1 0 -4 -2 1086.08 254.006 1 2 -4 5 7599.33 1252.17 -3 -4 3 -1 7599.33 1252.17 -2 0 -4 -2 7599.33 1252.17 1 0 -4 -3 15714.9 323.942 1 0 4 4 2800.23 278.645 1 0 -4 -5 10858.1 509.405 1 0 4 6 3100.65 484.109 1 0 -4 -7 2318.18 524.126 1 3 -3 5 2236.48 477.661 -3 -4 2 -2 2236.48 477.661 -2 0 -5 0 2236.48 477.661 1 0 -5 -1 23407.9 531.611 1 0 5 2 596.008 499.917 1 5 -4 1 5574.94 571.599 -2 0 5 3 5574.94 571.599 1 0 -5 -4 9195.90 519.394 1 0 -5 -5 501.113 513.942 1 0 -5 -6 3352.28 717.304 1 0 5 7 11548.6 960.115 1 0 -6 0 7460.09 541.312 1 0 6 1 24665.2 632.591 1 0 -6 -2 5257.08 589.034 1 0 -6 -3 48925.1 778.243 1 0 6 4 3376.23 808.851 1 0 -6 -5 1064.02 911.250 1 0 6 6 5434.01 655.372 1 0 6 7 4268.71 882.531 1 0 -7 0 2680.20 756.402 1 0 7 1 2283.67 848.502 1 0 -7 -2 2354.60 1080.43 1 0 -7 -3 6276.73 679.606 1 0 7 4 143.531 664.489 1 0 -7 -5-447.015 689.605 1 0 7 6 5049.79 782.659 1 0 -8 -1 14279.2 760.344 1 0 -8 -2 3465.91 756.965 1 0 -8 -4 15338.8 736.766 1 0 -8 -5 91498.7 974.687 1 0 8 6 1395.27 745.143 1 0 -9 -2 3241.90 804.374 1 0 -9 -3 325.709 797.290 1 0 9 4 26780.0 842.079 1 0 -9 -5 23292.9 856.554 1 0 -10 -3 2606.31 1377.48 1 -1 9 5 1269.10 1687.65 1 1 -9 -4 31430.1 1549.10 1 -1 8 5 2920.80 724.391 1 1 -8 -4 814.564 754.249 1 1 -8 -3 3596.53 1242.05 1 1 -7 -5 3492.35 723.575 1 -1 7 4 801.249 864.062 1 1 -7 -2 564.316 957.296 1 -1 6 5 2315.60 629.670 1 -1 6 4 6743.08 630.218 1 1 -6 -2 5779.05 588.280 1 -1 5 6 401.287 544.718 1 -1 5 5 2090.52 510.536 1 1 -5 -4 8768.08 354.667 1 -1 5 3 5533.45 438.834 1 1 -5 -2 4704.18 394.041 1 -1 4 8 2986.27 1092.39 1 -1 4 7 46.4954 487.900 1 1 -4 -5 5598.47 308.816 1 -1 4 4 12727.1 312.350 1 1 -4 -3 4054.34 271.735 1 1 -4 -2 6177.76 400.211 1 1 -4 -1 89908.0 896.027 1 1 -3 -10 1310.18 675.961 1 -1 3 8 7683.33 598.377 1 1 -3 -7 331.685 495.287 1 1 -3 -6 155825. 525.967 1 -1 3 5 34261.2 309.635 1 1 -3 -4 337.037 232.968 1 1 -3 -3 11215.8 291.672 1 1 -3 -2 226426. 1155.58 1 1 -2 -11 9615.06 1013.56 1 1 -2 -10 4783.64 929.258 1 -1 2 9 1140.73 759.062 1 1 -2 -8 5066.68 533.625 1 1 -2 -7 60298.1 623.948 1 1 -2 -6 361509. 666.943 1 1 -2 -5 12349.2 377.691 1 1 -2 -4 3242.07 190.190 1 -1 2 3 31271.7 519.305 1 -1 2 2 34305.0 202.934 1 1 -1 -10-576.740 848.613 1 1 -1 -9 87.2541 782.217 1 -1 1 8 6786.99 529.565 1 1 -1 -7 4184.80 450.724 1 1 -1 -5-20.0516 193.385 1 1 -1 -4 11855.4 241.588 1 1 -1 -2 5050.52 115.604 1 -1 1 1-39.6556 101.215 1 1 0 -8 3994.04 447.957 1 1 0 -7 8129.32 417.660 1 -1 0 6 10944.2 370.633 1 1 0 -5 26712.2 397.800 1 1 0 -3 217393. 519.201 1 -1 0 2 27058.4 183.319 1 1 0 -1 39524.3 171.368 1 1 1 -6 508.793 316.155 1 -1 -1 5 26513.6 334.294 1 1 1 -4 1612.95 265.282 1 1 1 -3 476.449 151.001 1 1 1 -2 220290. 281.472 1 1 1 -1 79047.1 275.824 1 1 1 0 55868.7 278.352 1 1 1 1 94275.2 393.168 1 1 1 2 46400.3 430.476 1 1 2 -3 92841.9 593.135 1 -1 -2 2 1450.46 122.855 1 1 2 -1 21305.7 236.874 1 -1 -2 0 22282.1 266.450 1 -1 -2 -1 72471.9 320.429 1 -1 -2 -2 358773. 700.601 1 1 2 3 698.174 257.443 1 1 2 4 3159.07 312.075 1 -1 -2 -5 15145.1 676.210 1 -1 -2 -6 207336. 1633.67 1 -1 -3 0 17832.4 321.693 1 1 3 1 248499. 352.489 1 1 3 2 35951.8 273.936 1 -1 -3 -3 513.435 519.476 1 -1 4 -6 822.334 886.932 -3 4 -3 -1 822.334 886.932 -2 1 3 3 822.334 886.932 1 1 3 4 741.001 352.955 1 1 3 5 317.483 523.279 1 -1 -3 -7 1643.59 1002.01 1 -1 -4 3 134119. 1099.85 1 -1 -4 2 29185.2 432.132 1 -1 -4 1 7298.03 373.534 1 -1 -4 0 74359.2 590.706 1 1 4 1 2460.91 262.934 1 -1 -4 -2 828.545 365.311 1 1 4 3 2206.70 474.154 1 1 4 4 349.778 439.783 1 -1 -4 -5 3089.84 511.112 1 1 4 6 2762.09 546.679 1 1 4 8 4458.14 848.846 1 -1 -5 1 68475.6 655.341 1 -1 -5 0 448.659 467.393 1 -1 -5 -1 14464.6 534.498 1 -1 -5 -2 487.984 491.986 1 -1 -5 -3 31667.8 591.880 1 1 5 4 16703.0 606.873 1 -1 -5 -6 628.332 578.049 1 1 5 7 2801.46 612.914 1 -1 -5 -8 16465.6 780.563 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3 464.374 371.243 3 3 -9 4 668.679 371.211 3 3 -9 5 279.781 369.271 3 -3 9 -6 222.395 777.585 3 3 -9 10-44.9362 299.303 3 3 -9 11 95.2744 313.895 3 3 -9 12 869.795 507.283 3 3 -8 -6-297.301 429.695 3 3 -8 -5-260.688 419.050 3 3 -8 -4-59.7498 403.587 3 -3 8 3 278.572 386.528 3 3 -8 -1-232.083 358.751 3 3 -8 0 166.556 351.727 3 3 -8 1 177.032 350.021 3 3 -8 3 344.224 453.562 3 3 -8 4 522.854 329.038 3 3 -8 5 520.720 333.127 3 -3 8 -6 288.974 409.782 3 -3 8 -7-415.389 395.408 3 3 -8 8 330.542 268.905 3 3 -8 9 92.5539 273.757 3 3 -8 10 419.682 290.064 3 3 -8 11 679.002 304.811 3 3 -8 12-195.557 314.995 3 3 -8 13-338.027 368.673 3 3 -7 -6 278.915 438.579 3 3 -7 -5-795.554 386.657 3 3 -7 -4-551.866 367.780 3 3 -7 -3-65.4747 353.623 3 3 -7 -2-80.2573 781.263 3 3 -7 -1-638.493 454.416 3 -3 7 0 249.255 320.932 3 3 -7 1 5077.61 348.480 3 -3 7 -2 2610.24 315.910 3 -3 7 -3 857.908 299.642 3 3 -7 4 32.8196 286.797 3 3 -7 5 440.980 174.496 3 3 -7 6 132.055 239.038 3 3 -7 7-87.2816 232.783 3 3 -7 8 257.681 363.296 3 3 -7 9-198.004 278.652 3 3 -7 11-35.5970 291.663 3 3 -7 12 91.9547 311.540 3 3 -7 13-108.041 315.888 3 3 -6 -7-724.828 885.507 3 3 -6 -4 1837.83 777.662 3 3 -6 -3 588.794 396.395 3 3 -6 -2 28.7902 699.015 3 3 -6 -1-471.520 359.574 3 3 -6 0-265.962 334.877 3 3 -6 2-76.2913 332.291 3 3 -6 3 563.398 213.431 3 3 -6 4 98.4045 160.587 3 3 -6 5 137.249 175.896 3 3 -6 6 172.368 229.386 3 3 -6 7-661.421 256.467 3 3 -6 9-243.786 263.278 3 3 -6 10-211.703 270.253 3 3 -6 11-195.916 289.723 3 3 -6 12-431.971 292.576 3 3 -6 13 409.410 321.128 3 3 -5 -6 79.3075 742.447 3 3 -5 -5 59.8469 679.236 3 3 -5 -4 1050.33 667.766 3 3 -5 -3-357.238 418.975 3 3 -5 -2-229.994 324.847 3 3 -5 -1-273.273 312.425 3 3 -5 0 380.700 294.803 3 -3 5 -1-127.715 277.491 3 3 -5 2-157.390 181.888 3 3 -5 3 1295.32 195.201 3 3 -5 4 1913.38 192.245 3 3 -5 5 570.163 179.361 3 3 -5 6 394.208 219.224 3 3 -5 7 921.015 243.402 3 3 -5 9 778.863 291.767 3 3 -5 10-502.485 280.309 3 3 -5 12 310.673 308.157 3 3 -5 13 215.454 323.037 3 3 -4 3 8419.50 278.726 3 3 -4 4 894.455 156.901 3 3 -4 5 922.424 229.919 3 3 -4 6 194.889 205.943 3 3 -4 7 1323.31 241.180 3 3 -4 9-68.5266 281.859 3 3 -4 10 84.1385 309.118 3 3 -4 11-1280.07 299.282 3 3 -4 12 438.558 306.105 3 3 -4 13 835.613 318.615 3 3 -3 4 81.9942 213.716 3 3 -3 6 639.472 204.890 3 3 -3 7 1360.11 234.313 3 3 -3 8 275.972 373.034 3 3 -3 9 700.566 266.209 3 3 -3 10 164.577 304.748 3 3 -3 11 590.085 278.658 3 3 -3 12 390.842 299.330 3 3 -3 13 409.142 317.588 3 3 -2 5-8.71031 250.437 3 3 -2 6 353.408 208.247 3 -3 2 -8 553.249 322.703 3 3 -2 9 343.796 272.527 3 3 -2 10 516.754 293.315 3 3 -2 11 569.864 320.444 3 3 -2 12 358.559 308.584 3 3 -2 13 480.146 326.476 3 3 -1 6 1098.00 342.045 3 3 -1 7 398.180 234.227 3 3 -1 8-182.414 323.154 3 3 -1 9 283.558 270.080 3 3 -1 10 110.765 299.470 3 3 -1 11 52.6972 357.243 3 3 -1 12-173.080 307.662 3 3 -1 13 510.322 522.809 3 3 0 7 3603.62 405.304 3 3 0 9 891.120 481.097 3 3 0 10 422.635 516.654 3 -4 12 -4 291.979 468.008 3 -4 12 -5 471.805 476.454 3 4 -11 -1-394.860 602.319 3 -4 11 0 741.675 979.921 3 4 -11 1-59.7954 445.722 3 4 -11 2-30.3382 450.497 3 4 -11 3-425.802 444.159 3 4 -11 4-1058.45 451.383 3 4 -11 5 879.585 458.268 3 4 -10 -4 2269.64 533.383 3 4 -10 -3 709.958 457.474 3 4 -10 -2 8.18698 440.894 3 4 -10 -1-54.7465 439.781 3 4 -10 0 1101.43 450.186 3 4 -10 1 15.1202 426.230 3 4 -10 2 0.38970 424.842 3 4 -10 3-97.5929 409.742 3 4 -10 4 540.457 428.132 3 4 -10 5-113.167 404.723 3 -4 9 5 191.412 755.895 3 4 -9 -4 69.8408 496.839 3 -4 9 3 881.596 436.985 3 4 -9 -2-91.4503 418.955 3 4 -9 -1-2018.47 419.814 3 4 -9 0-549.480 396.574 3 -4 9 -2 917.423 817.625 3 4 -9 3-452.901 381.093 3 4 -9 4 21.6020 386.108 3 4 -9 5-92.8964 382.436 3 4 -9 10 241.740 304.989 3 4 -9 11 826.914 323.594 3 4 -9 12 1277.02 339.272 3 4 -8 -3 786.358 595.392 3 -4 8 2 1211.76 507.713 3 4 -8 -1 720.719 594.562 3 4 -8 0 180.795 467.928 3 4 -8 1 165.711 444.909 3 4 -8 2 3972.61 483.739 3 -4 8 -3-607.324 532.338 3 -4 8 -4-316.929 546.230 3 4 -8 5 110.222 343.274 3 4 -8 7 416.511 281.352 3 4 -8 8 253.125 300.797 3 4 -8 9 346.927 276.430 3 4 -8 10 904.165 303.341 3 4 -8 11 717.398 315.817 3 -4 7 -1 1001.61 394.528 3 -4 7 -2 3465.72 511.138 3 4 -7 3 247.334 782.598 3 4 -7 4-254.946 735.916 3 4 -7 5-188.333 336.314 3 4 -7 6-98.0467 247.263 3 4 -7 8 663.250 307.419 3 4 -7 9 599.142 511.465 3 4 -7 10 866.503 294.174 3 4 -7 11 627.442 307.417 3 4 -7 12 255.752 317.700 3 4 -6 4 561.506 298.237 3 4 -6 6 85.6715 239.581 3 4 -6 7 27.8081 435.955 3 4 -6 8 622.331 277.350 3 4 -6 9 783.001 298.068 3 4 -6 10 145.690 313.381 3 4 -6 11 627.084 333.283 3 4 -6 12 283.600 320.809 3 4 -5 6 597.841 369.055 3 4 -5 8-20.0196 270.856 3 4 -5 9 926.780 297.922 3 4 -5 10 1045.52 323.217 3 4 -5 11 351.887 330.365 3 4 -5 12 392.855 316.915 3 4 -4 8 503.360 276.352 3 4 -4 9 330.635 304.644 3 4 -4 10 86.8428 304.587 3 4 -4 11-173.245 333.954 3 4 -4 12-83.2762 342.810 3 4 -3 9 219.177 291.614 3 4 -3 10 1233.52 310.312 3 4 -3 11 68.1115 325.962 3 4 -3 12 409.282 350.910 3 4 -2 11 2881.76 571.178 3 4 -2 12-364.283 586.232 3 -5 12 -5 759.213 578.933 3 5 -11 1 1044.24 517.125 3 5 -11 2 212.452 453.590 3 5 -11 3 168.989 503.540 3 5 -11 4 398.692 508.293 3 -5 11 -5 1857.79 761.468 3 5 -10 2-785.526 565.238 3 5 -10 3-44.9326 568.598 3 5 -10 4 320.142 576.219 3 5 -9 4-306.815 959.565 3 5 -9 10 354.271 462.101 3 5 -9 11-350.726 367.988 3 5 -8 7 1341.18 472.613 3 5 -8 8 1121.99 517.842 3 5 -8 9 331.887 595.611 3 5 -8 10 123.447 607.529 3 5 -8 11-270.530 315.949 3 5 -7 9 3073.98 554.173 3 5 -7 10 453.605 562.741 3 5 -7 11-385.017 922.821 3 ; _shelx_hkl_checksum 94108 _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 _atom_site_refinement_flags_adp O1 O 0.4123(13) 1.0195(7) 0.8106(7) 0.051(3) Uani 1 1 d . U C15 C 0.2386(15) 0.4739(8) 0.4567(8) 0.025(2) Uani 1 1 d . U C2 C 0.2922(15) 0.6599(8) 0.5555(9) 0.024(2) Uani 1 1 d . U C3 C 0.3270(15) 0.8004(9) 0.4982(9) 0.027(2) Uani 1 1 d . U H3 H 0.352128 0.921479 0.558694 0.032 Uiso 1 1 calc R . C14 C 0.2495(17) 0.5447(10) 0.7444(10) 0.038(3) Uani 1 1 d . U H14 H 0.247617 0.567838 0.839700 0.045 Uiso 1 1 calc R . C1 C 0.2971(15) 0.6893(9) 0.7015(9) 0.027(2) Uani 1 1 d . U C12 C 0.1973(13) 0.3275(9) 0.5046(9) 0.0194(17) Uani 1 1 d . U C9 C 0.1925(15) 0.2501(10) 0.2132(9) 0.027(2) Uani 1 1 d . U C8 C 0.1963(16) 0.2154(10) 0.0695(9) 0.030(3) Uani 1 1 d . U H8 H 0.173563 0.095818 0.006498 0.036 Uiso 1 1 calc R . C5 C 0.2758(16) 0.5774(9) 0.2575(9) 0.029(3) Uani 1 1 d . U C6 C 0.2769(17) 0.5366(10) 0.1135(10) 0.035(3) Uani 1 1 d . U H6 H 0.307239 0.631026 0.080507 0.042 Uiso 1 1 calc R . C7 C 0.2338(17) 0.3584(11) 0.0195(9) 0.034(3) Uani 1 1 d . U H7 H 0.229641 0.333058 -0.076795 0.040 Uiso 1 1 calc R . C4 C 0.3241(16) 0.7606(9) 0.3577(9) 0.031(3) Uani 1 1 d . U H4 H 0.354545 0.855918 0.325630 0.037 Uiso 1 1 calc R . C16 C 0.2370(15) 0.4318(9) 0.3099(9) 0.025(2) Uani 1 1 d . U C13 C 0.2043(14) 0.3656(9) 0.6500(9) 0.0214(19) Uani 1 1 d . U H13 H 0.178723 0.270620 0.682972 0.026 Uiso 1 1 calc R . C11 C 0.1480(15) 0.1434(9) 0.4033(9) 0.027(2) Uani 1 1 d . U H11 H 0.116643 0.047136 0.434229 0.032 Uiso 1 1 calc R . C17 C 0.3558(17) 0.8699(9) 0.8171(9) 0.038(3) Uani 1 1 d . U H17 H 0.349050 0.870074 0.907486 0.045 Uiso 1 1 calc R . C10 C 0.1461(17) 0.1070(10) 0.2636(10) 0.036(3) Uani 1 1 d . U H10 H 0.113970 -0.013419 0.200166 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 O1 0.091(6) 0.017(2) 0.036(4) 0.001(2) 0.029(5) 0.002(3) C15 0.039(6) 0.012(3) 0.022(4) 0.004(2) 0.012(4) 0.002(3) C2 0.035(5) 0.013(3) 0.024(4) 0.008(2) 0.011(4) 0.004(3) C3 0.038(6) 0.017(3) 0.026(4) 0.011(3) 0.011(4) 0.002(3) C14 0.058(7) 0.024(3) 0.031(5) 0.008(3) 0.023(5) 0.004(4) C1 0.040(6) 0.018(3) 0.027(4) 0.008(2) 0.019(4) 0.009(3) C12 0.018(4) 0.022(2) 0.021(3) 0.012(2) 0.000(3) 0.009(2) C9 0.034(6) 0.025(3) 0.024(4) 0.010(3) 0.008(4) 0.007(3) C8 0.045(6) 0.022(3) 0.025(4) 0.009(3) 0.015(5) 0.008(3) C5 0.046(6) 0.017(3) 0.026(4) 0.006(2) 0.018(5) 0.005(3) C6 0.053(7) 0.028(4) 0.026(5) 0.013(3) 0.011(5) 0.008(4) C7 0.055(7) 0.037(4) 0.009(4) 0.009(3) 0.004(5) 0.011(4) C4 0.050(7) 0.017(3) 0.030(4) 0.010(3) 0.021(5) 0.003(3) C16 0.037(6) 0.017(3) 0.022(4) 0.008(2) 0.010(4) 0.006(3) C13 0.029(5) 0.021(3) 0.024(4) 0.018(3) 0.003(4) 0.014(3) C11 0.043(6) 0.012(3) 0.035(5) 0.017(3) 0.015(5) 0.008(3) C17 0.068(7) 0.017(3) 0.029(5) 0.004(3) 0.028(6) 0.010(3) C10 0.065(7) 0.014(3) 0.031(5) 0.007(3) 0.022(5) 0.009(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0010 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 C12 C15 C2 120.8(7) C12 C15 C16 118.1(6) C16 C15 C2 121.0(7) C3 C2 C15 117.5(7) C1 C2 C15 117.2(7) C1 C2 C3 125.3(6) C2 C3 H3 119.2 C4 C3 C2 121.5(6) C4 C3 H3 119.2 C1 C14 H14 119.0 C1 C14 C13 122.0(7) C13 C14 H14 119.0 C2 C1 C17 124.3(7) C14 C1 C2 120.8(6) C14 C1 C17 114.8(7) C15 C12 C11 119.3(7) C13 C12 C15 119.3(6) C13 C12 C11 121.4(8) C8 C9 C16 119.4(8) C8 C9 C10 121.6(6) C16 C9 C10 119.1(7) C9 C8 H8 119.5 C7 C8 C9 120.9(6) C7 C8 H8 119.5 C6 C5 C4 122.2(8) C6 C5 C16 119.5(6) C4 C5 C16 118.2(7) C5 C6 H6 119.5 C7 C6 C5 121.0(9) C7 C6 H6 119.5 C8 C7 H7 120.1 C6 C7 C8 119.9(8) C6 C7 H7 120.1 C3 C4 C5 122.2(8) C3 C4 H4 118.9 C5 C4 H4 118.9 C15 C16 C5 119.4(6) C9 C16 C15 121.5(8) C9 C16 C5 119.1(7) C14 C13 C12 119.9(8) C14 C13 H13 120.1 C12 C13 H13 120.1 C12 C11 H11 119.3 C10 C11 C12 121.4(8) C10 C11 H11 119.3 O1 C17 C1 128.7(8) O1 C17 H17 115.7 C1 C17 H17 115.7 C9 C10 H10 119.7 C11 C10 C9 120.7(6) C11 C10 H10 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C17 1.218(10) C15 C2 1.437(8) C15 C12 1.416(12) C15 C16 1.420(11) C2 C3 1.434(12) C2 C1 1.423(12) C3 H3 0.9300 C3 C4 1.358(11) C14 H14 0.9300 C14 C1 1.374(13) C14 C13 1.385(9) C1 C17 1.468(8) C12 C13 1.403(12) C12 C11 1.436(8) C9 C8 1.405(12) C9 C16 1.409(8) C9 C10 1.412(13) C8 H8 0.9300 C8 C7 1.402(14) C5 C6 1.397(12) C5 C4 1.427(8) C5 C16 1.439(13) C6 H6 0.9300 C6 C7 1.379(10) C7 H7 0.9300 C4 H4 0.9300 C13 H13 0.9300 C11 H11 0.9300 C11 C10 1.355(12) C17 H17 0.9300 C10 H10 0.9300 loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.7193 2586 91 2 0.2488 2396 93 3 0.0319 2711 79 loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.725(6) 2 0.237(6) 3 0.0377(16) _cod_database_fobs_code 2108399