#------------------------------------------------------------------------------ #$Date: 2024-08-05 21:00:32 +0300 (Mon, 05 Aug 2024) $ #$Revision: 293752 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571886.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_1571886 loop_ _publ_author_name 'Zhao, Yankun' 'Yan, Hongya' 'Zhang, Yulian' 'Zhou, Tao' 'Tian, Mengxing' 'Zhang, Chongzhou' 'Yuan, Shan' 'Qiu, Hanyue' 'He, Ling' 'Zhang, Min' _publ_section_title ; Catalytic asymmetric intramolecular propargylation of cyclopropanols to access the cuparane core. ; _journal_issue 28 _journal_name_full 'Chemical science' _journal_page_first 10963 _journal_page_last 10968 _journal_paper_doi 10.1039/d4sc02504k _journal_volume 15 _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H15 Br O' _chemical_formula_sum 'C15 H15 Br O' _chemical_formula_weight 291.18 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-05-16 _audit_creation_method ; Olex2 1.5 (compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410) ; _audit_update_record ; 2023-12-22 deposited with the CCDC. 2024-06-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0877(6) _cell_length_b 10.7172(12) _cell_length_c 14.3707(11) _cell_measurement_reflns_used 1546 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.3120 _cell_measurement_theta_min 2.3620 _cell_volume 1399.6(2) _computing_cell_refinement 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _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 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0892 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.883 _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 2.00 37.00 1.00 24.00 -- 18.74 77.00 -60.00 35 2 \w 21.00 87.00 1.00 24.00 -- 18.74 57.00 90.00 66 3 \w -81.00 17.00 1.00 24.00 -- -18.93 -19.00-180.00 98 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset/far, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0089053000 _diffrn_orient_matrix_UB_12 -0.0271056000 _diffrn_orient_matrix_UB_13 0.0446784000 _diffrn_orient_matrix_UB_21 -0.0459041000 _diffrn_orient_matrix_UB_22 0.0467915000 _diffrn_orient_matrix_UB_23 0.0194024000 _diffrn_orient_matrix_UB_31 -0.0624462000 _diffrn_orient_matrix_UB_32 -0.0382370000 _diffrn_orient_matrix_UB_33 -0.0079122000 _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 0.0288 _diffrn_reflns_av_unetI/netI 0.0611 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.883 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5784 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.850 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.089 _diffrn_reflns_theta_min 2.371 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.919 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.382 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.623 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details ; Flack x determined using 491 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.006(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 3195 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.1258 _refine_ls_R_factor_gt 0.0565 _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^)+(0.0452P)^2^+0.9495P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.1420 _reflns_Friedel_coverage 0.683 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.806 _reflns_number_gt 1681 _reflns_number_total 3195 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02504k2.cif _cod_data_source_block 20220516-zyk-09113 _cod_depositor_comments 'Adding full bibliography for 1571886--1571889.cif.' _cod_database_code 1571886 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H15 Br O' _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 ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C4(H4A,H4B) 2.b Aromatic/amide H refined with riding coordinates: C15(H15), C11(H11), C13(H13), C12(H12) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C) 2.d : C1(H1) ; _shelx_res_file ; TITL 20220516-zyk-09113_a.res in P2(1)2(1)2(1) 20220516-zyk-09113.res created by SHELXL-2018/3 at 16:05:04 on 16-May-2022 REM Old TITL 20220516-Zhang Min-ZYK-09113_auto in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.204, Rweak 0.164, Alpha 0.002 REM 1.650 for 21 systematic absences, Orientation as input REM Flack x = 0.040 ( 0.011 ) from 545 Parsons' quotients REM Formula found by SHELXT: C14 O2 Br CELL 0.71073 9.0877 10.7172 14.3707 90 90 90 ZERR 4 0.0006 0.0012 0.0011 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Br O UNIT 60 60 4 4 L.S. 30 PLAN 5 CONF BOND list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.045200 0.949500 FVAR 0.52221 BR1 3 0.344124 0.710164 0.502983 11.00000 0.10034 0.13650 = 0.07460 -0.00186 0.03348 0.01395 O1 4 0.959898 0.781725 0.080831 11.00000 0.06475 0.10644 = 0.06219 -0.00982 0.01618 -0.02664 C10 1 0.505424 0.650318 0.237489 11.00000 0.04919 0.04255 = 0.05342 0.00685 -0.00203 0.00059 C3 1 0.657672 0.634044 0.194362 11.00000 0.05028 0.04474 = 0.04413 0.00026 -0.00249 0.00625 C15 1 0.493885 0.668340 0.333241 11.00000 0.04592 0.05969 = 0.05598 0.00580 0.00382 -0.00134 AFIX 43 H15 2 0.577537 0.666393 0.370491 11.00000 -1.20000 AFIX 0 C7 1 0.734688 0.760552 0.169221 11.00000 0.04605 0.05341 = 0.03779 -0.00115 -0.00482 -0.00413 C6 1 0.852279 0.720920 0.100050 11.00000 0.05669 0.07224 = 0.03965 0.00157 -0.00177 -0.00575 C14 1 0.356962 0.689163 0.372498 11.00000 0.05641 0.05310 = 0.07148 0.00648 0.01426 0.00279 C8 1 0.631412 0.848264 0.115738 11.00000 0.07512 0.05045 = 0.07122 0.00886 -0.00316 0.00134 AFIX 137 H8A 2 0.594118 0.806180 0.061688 11.00000 -1.50000 H8B 2 0.684621 0.921409 0.096903 11.00000 -1.50000 H8C 2 0.550893 0.872070 0.155168 11.00000 -1.50000 AFIX 0 C2 1 0.754248 0.562659 0.259186 11.00000 0.05615 0.06163 = 0.05204 0.01154 0.01281 0.00966 C5 1 0.811734 0.596244 0.059382 11.00000 0.07946 0.08033 = 0.05216 -0.01632 0.01394 0.00141 AFIX 23 H5A 2 0.884011 0.533674 0.076398 11.00000 -1.20000 H5B 2 0.806838 0.601185 -0.007945 11.00000 -1.20000 AFIX 0 C4 1 0.662535 0.563457 0.099378 11.00000 0.07364 0.05672 = 0.05590 -0.00912 0.00371 -0.00441 AFIX 23 H4A 2 0.653427 0.474121 0.108548 11.00000 -1.20000 H4B 2 0.584105 0.591456 0.058633 11.00000 -1.20000 AFIX 0 C9 1 0.801116 0.831366 0.252357 11.00000 0.06103 0.07172 = 0.04865 -0.01611 0.00343 -0.01088 AFIX 137 H9A 2 0.724682 0.851339 0.295997 11.00000 -1.50000 H9B 2 0.846415 0.906931 0.230764 11.00000 -1.50000 H9C 2 0.873692 0.780008 0.282176 11.00000 -1.50000 AFIX 0 C11 1 0.378194 0.653568 0.185103 11.00000 0.05887 0.07252 = 0.06744 0.00556 -0.01256 -0.00256 AFIX 43 H11 2 0.383090 0.641387 0.121104 11.00000 -1.20000 AFIX 0 C13 1 0.231991 0.691964 0.320394 11.00000 0.05987 0.07095 = 0.10044 0.00545 0.01182 0.01188 AFIX 43 H13 2 0.140828 0.705322 0.348058 11.00000 -1.20000 AFIX 0 C1 1 0.832268 0.506283 0.307184 11.00000 0.06793 0.09326 = 0.07306 0.01966 0.00985 0.03500 AFIX 163 H1 2 0.894866 0.461051 0.345694 11.00000 -1.20000 AFIX 0 C12 1 0.243504 0.674783 0.226977 11.00000 0.04187 0.09299 = 0.10331 -0.00314 -0.01816 0.00192 AFIX 43 H12 2 0.159064 0.677348 0.190467 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20220516-zyk-09113_a.res in P2(1)2(1)2(1) REM wR2 = 0.1420, GooF = S = 1.016, Restrained GooF = 1.016 for all data REM R1 = 0.0565 for 1681 Fo > 4sig(Fo) and 0.1258 for all 3195 data REM 156 parameters refined using 0 restraints END WGHT 0.0451 0.9531 REM Highest difference peak 0.623, deepest hole -0.491, 1-sigma level 0.056 Q1 1 0.2693 0.7006 0.4507 11.00000 0.05 0.62 Q2 1 0.3449 0.7770 0.5201 11.00000 0.05 0.22 Q3 1 0.2223 0.8220 0.5016 11.00000 0.05 0.22 Q4 1 0.2513 0.7431 0.5660 11.00000 0.05 0.20 Q5 1 0.0416 0.6997 0.4582 11.00000 0.05 0.19 ; _shelx_res_checksum 7975 _shelx_hkl_file ; 0 0 -2 27.71 1.96 0 0 2 30.01 2.01 0 0 -3 -0.61 0.83 0 0 3 0.10 0.93 0 0 4 1674.69 27.86 0 0 -4 1674.82 28.05 0 0 5 0.75 1.54 0 0 -5 0.98 0.97 0 0 6 656.83 17.43 0 0 7 -1.24 2.43 0 0 8 756.91 21.89 0 0 9 1.99 2.86 0 0 10 648.47 22.38 0 0 11 5.35 3.74 0 0 12 545.07 22.64 0 0 13 8.23 4.78 0 0 14 12.43 5.35 0 0 15 13.07 5.02 0 0 16 74.14 10.37 0 0 17 0.49 3.59 0 0 18 9.58 5.40 0 1 0 0.67 0.36 0 -1 0 0.11 0.22 0 1 1 622.02 10.02 0 -1 -1 647.84 9.19 0 -1 -1 618.30 10.10 0 1 2 0.96 0.50 0 1 2 0.96 0.79 0 -1 -2 1.13 0.48 0 -1 -2 2.49 0.89 0 1 3 4103.87 54.58 0 -1 -3 4145.09 50.59 0 -1 -3 4126.57 54.45 0 1 -3 4095.62 54.44 0 -1 3 4133.21 54.13 0 1 -4 226.23 8.31 0 -1 -4 229.42 6.29 0 -1 -4 231.70 8.31 0 1 4 227.07 8.28 0 -1 4 230.24 8.32 0 1 -5 3069.94 47.85 0 -1 5 3136.82 47.51 0 -1 -5 3155.14 42.33 0 1 5 3140.22 47.78 0 -1 -5 3183.86 47.81 0 -1 -6 74.43 4.13 0 -1 6 87.37 6.43 0 1 6 74.57 5.86 0 -1 7 3257.24 52.69 0 1 7 3227.31 52.78 0 -1 -7 3125.80 45.33 0 1 8 30.78 4.82 0 -1 -8 29.30 3.14 0 -1 8 37.90 5.64 0 1 9 454.34 17.77 0 -1 9 469.22 17.71 0 -1 -9 442.95 13.20 0 -1 10 3.16 3.78 0 1 10 2.04 3.56 0 -1 -10 -1.39 1.87 0 -1 -11 107.17 6.86 0 1 11 116.20 9.94 0 -1 11 122.12 10.40 0 -1 -12 -0.23 1.67 0 -1 12 1.99 3.91 0 1 12 8.95 4.53 0 1 13 136.77 11.78 0 -1 -13 116.99 7.95 0 -1 13 131.27 11.51 0 -1 14 5.68 4.58 0 1 14 8.68 5.12 0 -1 15 73.70 9.56 0 1 15 76.64 9.85 0 1 16 5.98 4.37 0 1 17 11.85 5.48 0 1 18 5.38 5.09 0 2 0 9834.60 117.53 0 -2 0 9999.00 117.71 0 2 1 2642.28 35.62 0 -2 1 2570.86 35.65 0 2 1 2587.52 35.55 0 2 1 2541.88 34.94 0 -2 -2 1499.64 22.19 0 -2 -2 1536.38 24.22 0 2 2 1465.53 23.97 0 2 2 1474.83 22.25 0 -2 -3 125.83 4.59 0 2 3 115.84 4.52 0 2 3 118.90 5.78 0 -2 -3 120.51 5.70 0 2 4 703.21 13.59 0 -2 -4 720.37 16.87 0 2 4 716.74 16.80 0 -2 -4 708.73 13.42 0 2 -4 708.04 16.73 0 2 5 7.63 2.23 0 -2 -5 6.96 1.39 0 2 6 1187.91 26.56 0 -2 -6 1206.82 21.02 0 2 7 45.85 5.42 0 -2 -7 46.63 3.62 0 2 8 554.45 19.07 0 -2 -8 568.57 14.28 0 -2 -9 53.49 4.54 0 2 9 55.35 6.79 0 2 10 297.37 15.20 0 -2 -10 309.00 11.30 0 2 11 4.92 3.48 0 -2 -11 8.78 2.68 0 2 12 291.01 16.67 0 -2 -12 270.46 11.40 0 2 13 -5.57 4.55 0 -2 -13 5.32 2.43 0 2 14 32.96 6.69 0 2 15 7.38 3.96 0 2 16 19.39 5.79 0 2 17 4.20 4.47 0 3 0 1.55 1.40 0 -3 0 2.15 1.22 0 -3 1 2079.54 32.64 0 3 -1 2078.31 32.92 0 3 1 2123.08 32.64 0 3 1 2041.01 32.37 0 3 2 203.39 7.26 0 3 2 195.46 7.65 0 -3 2 202.55 7.64 0 -3 -2 217.00 8.01 0 3 2 206.22 7.77 0 3 3 881.62 19.42 0 -3 -3 929.97 17.43 0 3 3 869.69 17.51 0 -3 -3 956.38 19.87 0 -3 -4 266.81 8.26 0 3 4 254.93 10.21 0 -3 -4 276.54 10.32 0 3 4 272.90 8.44 0 -3 -5 871.95 17.28 0 3 5 901.01 21.28 0 3 5 860.43 17.26 0 -3 -6 649.74 14.68 0 3 6 685.91 19.32 0 3 6 622.31 14.63 0 -3 -7 418.92 11.80 0 3 7 456.55 16.44 0 -3 -8 37.35 3.64 0 3 8 36.68 5.31 0 3 9 301.94 15.00 0 -3 -9 268.63 9.98 0 -3 -10 26.01 3.38 0 3 10 20.99 4.94 0 -3 -11 61.05 4.98 0 3 11 56.70 7.74 0 3 12 11.58 5.18 0 -3 -12 7.71 2.25 0 3 13 15.87 4.75 0 3 14 5.43 4.33 0 3 15 72.93 9.65 0 3 16 7.38 5.30 0 3 17 8.33 5.22 0 -4 0 60.19 4.62 0 4 0 58.37 4.93 0 4 -1 91.65 6.02 0 4 1 86.78 5.84 0 -4 1 78.45 5.25 0 -4 -1 76.60 5.21 0 4 2 1083.77 22.63 0 4 2 1067.48 21.94 0 4 2 1007.76 22.30 0 4 3 130.55 6.55 0 4 3 133.18 7.39 0 4 3 128.76 7.33 0 4 4 27.45 3.91 0 4 4 33.16 3.19 0 -4 -5 452.09 12.53 0 4 5 413.46 12.22 0 4 5 434.46 15.30 0 -4 -6 251.13 9.37 0 4 6 247.18 11.89 0 4 6 244.73 9.12 0 4 7 62.87 6.64 0 4 7 58.45 4.50 0 -4 -7 61.10 4.54 0 4 8 77.47 7.57 0 -4 -8 73.62 5.18 0 -4 -9 5.89 2.12 0 4 9 3.61 3.56 0 -4 -10 136.26 7.43 0 4 10 132.00 10.68 0 -4 -11 4.40 2.06 0 4 11 0.92 3.81 0 4 12 84.99 9.64 0 -4 -12 76.12 5.84 0 4 13 7.74 4.16 0 4 14 14.75 5.69 0 4 15 -0.11 4.40 0 4 16 -3.50 3.94 0 4 17 0.00 3.93 0 5 0 12.96 3.61 0 5 -1 3.78 2.67 0 5 1 7.44 3.70 0 5 2 418.62 14.41 0 5 2 408.44 14.35 0 5 3 45.74 4.88 0 5 3 39.62 4.71 0 5 4 4.20 2.60 0 5 4 -0.27 2.60 0 5 5 375.59 15.19 0 5 6 8.84 3.57 0 5 7 0.20 3.26 0 -5 -7 3.64 2.08 0 -5 -8 6.66 2.32 0 5 8 11.29 4.19 0 -5 -9 95.15 6.60 0 5 9 97.01 9.08 0 -5 -10 66.88 5.56 0 5 10 61.94 7.57 0 -5 -11 4.64 2.12 0 5 11 1.67 3.77 0 5 12 3.87 3.41 0 5 13 4.44 4.14 0 5 14 16.95 5.87 0 5 15 3.96 3.48 0 5 16 -4.78 4.46 0 6 0 216.36 11.58 0 6 -1 5.70 3.54 0 6 1 6.01 3.77 0 6 2 340.67 14.35 0 6 2 335.40 14.16 0 6 3 36.31 5.56 0 6 3 45.18 6.19 0 6 4 7.84 2.97 0 6 4 4.49 2.87 0 6 5 27.00 4.72 0 6 5 23.05 4.88 0 6 6 35.68 6.18 0 6 6 25.11 4.88 0 6 7 52.28 6.70 0 6 8 1.64 2.88 0 6 9 10.33 4.77 0 6 10 1.65 3.73 0 6 11 0.49 3.40 0 6 12 8.56 5.23 0 6 13 -1.28 2.96 0 6 14 7.47 4.33 0 6 15 4.41 4.31 0 6 16 4.97 3.87 0 7 0 37.99 6.24 0 7 1 123.23 9.31 0 7 1 123.93 9.23 0 7 2 1.44 3.65 0 7 2 1.34 2.87 0 7 3 12.49 4.23 0 7 3 18.10 4.36 0 7 4 54.20 6.99 0 7 4 52.54 6.74 0 7 5 27.36 5.63 0 7 5 17.77 4.52 0 7 6 48.16 6.63 0 7 6 51.18 6.99 0 7 7 24.97 5.06 0 7 7 32.53 6.23 0 7 8 -0.47 3.36 0 7 8 -6.57 4.40 0 7 9 8.27 4.43 0 7 10 -0.50 3.82 0 7 11 0.54 3.86 0 7 12 2.27 3.04 0 7 13 -0.09 4.11 0 7 14 8.35 5.08 0 7 15 8.41 5.12 0 8 0 86.96 8.91 0 8 1 28.03 5.80 0 8 1 22.23 5.09 0 8 2 22.42 5.33 0 8 2 23.83 5.87 0 8 3 41.61 6.41 0 8 3 41.98 6.06 0 8 4 12.93 4.65 0 8 4 14.10 4.66 0 8 5 7.21 4.37 0 8 5 0.94 3.55 0 8 6 9.36 4.35 0 8 6 7.46 3.44 0 8 7 12.39 4.89 0 8 7 20.00 5.36 0 8 8 58.70 7.80 0 8 8 68.21 8.41 0 8 9 3.77 4.07 0 8 9 1.69 3.23 0 8 10 1.84 3.92 0 8 10 1.43 3.79 0 8 11 2.73 3.47 0 8 11 2.39 3.77 0 8 12 4.04 4.09 0 8 12 4.37 3.91 0 8 13 -9.01 4.41 0 8 13 7.55 4.57 0 8 14 7.50 4.91 0 8 14 0.00 3.45 0 8 15 -6.93 3.82 0 8 16 0.00 2.49 0 9 0 4.74 4.49 0 9 1 49.39 6.99 0 9 1 50.28 7.10 0 9 2 1.50 3.43 0 9 2 4.77 4.14 0 9 3 25.11 5.92 0 9 3 24.58 5.91 0 9 4 -2.78 3.25 0 9 4 7.49 4.80 0 9 5 50.77 7.43 0 9 5 72.36 8.68 0 9 6 12.87 4.93 0 9 6 7.00 3.85 0 9 7 11.45 4.63 0 9 7 19.04 5.34 0 9 8 5.83 3.64 0 9 8 0.25 3.95 0 9 9 8.55 4.43 0 9 9 11.94 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2.85 3.69 9 -8 -2 3.44 4.16 -9 8 -3 2.06 4.34 9 8 3 -4.18 3.30 -9 9 4 4.84 3.63 -9 9 3 6.56 4.48 -9 9 2 0.00 3.48 -9 9 1 0.00 3.54 -9 9 0 -12.91 5.39 -9 9 -1 8.74 4.33 9 9 2 1.87 2.43 -9 9 -2 0.00 3.54 -9 9 -3 8.86 5.07 9 9 3 0.00 2.58 9 9 4 0.00 2.91 10 0 0 55.13 8.08 10 0 1 -9.38 4.51 10 0 -1 1.02 3.32 10 0 2 16.89 4.75 10 0 -2 5.84 3.66 10 0 3 0.76 2.60 10 0 -3 0.77 3.48 10 0 -4 6.44 5.10 10 0 -5 12.42 5.96 10 0 -6 13.42 5.89 10 0 -7 5.01 3.90 10 0 -8 16.02 6.75 10 1 -8 14.36 6.44 10 1 -7 10.49 5.00 10 1 -6 1.28 4.26 10 1 -5 5.42 4.73 10 1 -4 7.27 4.92 10 -1 3 24.20 5.18 10 1 -3 23.00 5.94 10 -1 2 -2.62 3.23 10 1 -2 3.50 3.99 10 -1 1 6.33 3.84 10 1 -1 12.68 4.69 10 -1 0 5.26 3.79 10 1 0 -1.06 2.84 10 -1 -1 0.96 3.52 10 1 1 9.08 3.65 10 1 2 -1.75 2.73 10 -1 -2 -5.13 5.09 10 -1 -3 29.11 6.38 10 -1 -4 6.24 4.39 10 -1 -5 6.68 4.06 10 -1 -6 0.33 3.00 10 -1 -7 18.17 6.21 10 -1 -8 0.00 4.46 10 2 -8 0.00 3.73 10 2 -7 6.33 4.46 10 2 -6 3.38 4.61 10 2 -5 -4.03 4.15 10 2 -4 11.05 5.11 10 -2 4 4.97 3.39 10 2 -3 1.15 3.64 10 -2 3 4.92 3.34 10 -2 2 14.05 4.61 10 2 -2 16.86 5.07 10 -2 1 1.42 3.47 10 2 -1 1.67 2.83 10 -2 0 9.12 3.62 10 2 0 17.78 5.02 10 -2 -1 8.42 5.07 10 2 1 3.67 2.82 10 -2 -2 16.63 6.03 10 2 2 17.98 4.30 10 -2 -3 7.68 5.55 10 -2 -4 5.21 4.53 10 -2 -5 2.95 4.64 10 -2 -6 7.90 5.15 10 -2 -7 1.04 4.43 10 -2 -8 7.89 4.96 10 3 -8 2.01 4.47 10 3 -7 12.69 6.50 10 3 -6 15.30 6.05 10 3 -5 3.08 4.33 10 3 -4 1.40 3.62 10 -3 4 3.10 3.23 10 3 -3 -0.01 3.69 10 -3 3 10.83 4.28 10 3 -2 5.14 4.22 10 -3 2 1.38 2.97 10 -3 1 9.08 4.43 10 3 -1 2.63 3.33 10 -3 0 6.68 4.39 10 3 0 -3.04 2.70 10 -3 -1 7.82 3.98 10 3 1 4.52 3.36 10 -3 -2 1.63 3.91 10 -3 -3 6.71 4.79 10 -3 -4 -1.96 4.20 10 -3 -5 6.42 4.52 10 -3 -6 9.06 5.20 10 -3 -7 5.70 4.61 10 4 -7 1.47 3.52 10 4 -6 -8.13 4.87 10 4 -5 0.00 3.86 10 4 -4 -1.43 4.20 10 -4 4 2.91 3.37 10 4 -3 -1.34 3.83 10 -4 3 -1.92 3.14 10 4 -2 -1.32 3.11 10 -4 2 4.36 4.15 10 4 -1 3.94 3.92 10 -4 1 -5.08 4.36 10 4 0 11.00 4.18 10 -4 0 12.92 5.30 10 -4 -1 -3.12 3.79 10 4 1 -0.79 2.25 10 -4 -2 4.14 4.09 10 -4 -3 0.00 4.21 10 -4 -4 1.83 4.18 10 -4 -5 6.14 5.41 10 -4 -6 4.38 5.51 10 5 -6 -1.74 3.25 10 5 -5 0.00 3.86 10 -5 4 0.54 2.42 10 5 -4 -1.11 2.73 10 -5 3 -2.92 3.80 10 5 -3 3.26 3.16 10 5 -2 1.35 3.31 10 -5 2 0.22 3.84 10 5 -1 0.09 3.02 10 -5 1 -2.38 4.29 10 5 0 -5.51 3.87 10 -5 0 6.76 4.20 10 -5 -1 -7.83 4.78 10 -5 -2 1.87 4.16 10 -5 -3 4.15 4.45 10 -5 -4 5.47 5.04 10 -5 -5 9.80 5.68 10 6 -4 0.38 2.75 10 6 -3 -2.99 3.56 10 -6 2 0.65 3.97 10 6 -2 -8.89 4.85 10 -6 1 -8.89 4.98 10 6 -1 -2.65 3.34 10 -6 0 7.35 4.40 10 -6 -1 -3.96 3.87 10 -6 -2 -6.44 4.38 10 -6 -3 4.80 4.52 10 -7 1 3.31 4.35 10 -7 0 -0.99 3.20 11 0 0 -2.37 3.83 11 0 1 2.33 3.28 11 0 -1 -2.69 3.80 11 0 -2 -1.84 3.38 11 0 -3 -2.68 4.35 11 0 -4 -2.09 3.25 11 0 -5 6.49 5.43 11 1 -5 1.97 3.37 11 1 -4 4.32 4.27 11 1 -3 2.05 4.00 11 -1 2 1.18 2.95 11 1 -2 3.54 3.43 11 -1 1 1.35 3.42 11 1 -1 0.11 2.70 11 -1 0 0.17 3.20 11 1 0 -2.46 3.44 11 -1 -1 0.06 3.89 11 1 1 3.93 2.98 11 -1 -2 -5.92 4.49 11 -1 -3 -4.53 5.12 11 -1 -4 -7.39 4.41 11 -1 -5 0.00 3.65 11 2 -5 5.96 5.47 11 2 -4 5.99 4.62 11 2 -3 4.07 4.71 11 -2 2 2.67 3.01 11 2 -2 7.89 4.11 11 -2 1 4.36 4.34 11 2 -1 -0.09 2.27 11 -2 0 -1.16 2.91 11 2 0 1.95 2.88 11 -2 -1 5.70 4.81 11 -2 -2 2.88 3.99 11 -2 -3 0.00 3.61 11 -2 -4 2.22 4.93 11 -2 -5 1.34 3.91 11 3 -5 0.02 4.14 11 3 -4 4.66 5.20 11 3 -3 0.46 3.33 11 -3 3 2.58 3.44 11 3 -2 -6.01 4.13 11 -3 2 5.01 4.08 11 3 -1 6.14 3.72 11 -3 1 2.65 3.96 11 -3 0 0.52 2.91 11 3 0 -1.15 2.52 11 -3 -1 4.15 4.53 11 -3 -2 14.21 6.15 11 -3 -3 0.02 3.37 11 -3 -4 3.37 5.26 11 4 -5 -2.77 4.09 11 4 -4 -5.60 4.17 11 4 -3 4.09 4.06 11 -4 3 8.18 4.89 11 4 -2 11.02 4.96 11 -4 2 2.57 4.01 11 4 -1 2.16 3.11 11 -4 1 1.62 3.62 11 -4 0 1.10 2.97 11 -4 -1 3.04 4.15 11 -4 -2 2.16 4.21 11 -4 -3 8.02 4.91 11 5 -4 0.70 2.67 11 5 -3 -2.04 3.08 11 -5 3 2.34 3.30 11 5 -2 -3.17 3.52 11 -5 2 0.19 3.13 11 -5 1 -14.83 5.70 11 -5 0 0.33 3.08 11 -5 -1 3.82 4.88 11 6 -3 -0.45 2.50 12 0 0 2.79 3.75 12 0 -1 -2.01 3.58 12 0 -2 2.61 4.72 12 1 -2 2.02 4.37 12 1 -1 -1.89 3.78 12 -1 0 -2.11 4.00 12 -1 -1 0.22 3.01 12 -1 -2 1.89 4.13 12 2 -2 -8.19 4.20 12 -2 1 2.12 3.61 12 2 -1 2.53 3.29 12 -2 0 0.71 3.83 12 -2 -1 7.90 4.89 12 3 -2 1.14 3.78 12 -3 1 0.84 3.78 0 0 0 0.00 0.00 TITL 20220516-Zhang Min-ZYK-09113_auto in P2(1)2(1)2(1) REM P2(1)2(1)2(1) (#19 in standard setting) CELL 0.71073 9.087679 10.717156 14.370652 90.0000 90.0000 90.0000 ZERR 5.00 0.000577 0.001185 0.001092 0.0000 0.0000 0.0000 LATT -1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y+1/2,-z SFAC C H O Br UNIT 75.00 75.00 5.00 5.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 62148 _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 1.103 _oxdiff_exptl_absorpt_empirical_full_min 0.913 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.34412(11) 0.71016(11) 0.50298(7) 0.1038(5) Uani 1 1 d . . . . . O1 O 0.9599(6) 0.7817(6) 0.0808(3) 0.0778(17) Uani 1 1 d . . . . . C10 C 0.5054(7) 0.6503(6) 0.2375(5) 0.0484(16) Uani 1 1 d . . . . . C3 C 0.6577(7) 0.6340(6) 0.1944(4) 0.0464(15) Uani 1 1 d . . . . . C15 C 0.4939(7) 0.6683(6) 0.3332(5) 0.0539(18) Uani 1 1 d . . . . . H15 H 0.577537 0.666393 0.370491 0.065 Uiso 1 1 calc R U . . . C7 C 0.7347(7) 0.7606(6) 0.1692(4) 0.0458(17) Uani 1 1 d . . . . . C6 C 0.8523(8) 0.7209(8) 0.1000(4) 0.0562(18) Uani 1 1 d . . . . . C14 C 0.3570(8) 0.6892(7) 0.3725(5) 0.0603(19) Uani 1 1 d . . . . . C8 C 0.6314(9) 0.8483(7) 0.1157(5) 0.066(2) Uani 1 1 d . . . . . H8A H 0.594118 0.806180 0.061688 0.098 Uiso 1 1 calc R U . . . H8B H 0.684621 0.921409 0.096903 0.098 Uiso 1 1 calc R U . . . H8C H 0.550893 0.872070 0.155168 0.098 Uiso 1 1 calc R U . . . C2 C 0.7542(9) 0.5627(7) 0.2592(5) 0.0566(19) Uani 1 1 d . . . . . C5 C 0.8117(8) 0.5962(8) 0.0594(5) 0.071(2) Uani 1 1 d . . . . . H5A H 0.884011 0.533674 0.076398 0.085 Uiso 1 1 calc R U . . . H5B H 0.806838 0.601185 -0.007945 0.085 Uiso 1 1 calc R U . . . C4 C 0.6625(9) 0.5635(7) 0.0994(5) 0.062(2) Uani 1 1 d . . . . . H4A H 0.653427 0.474121 0.108548 0.075 Uiso 1 1 calc R U . . . H4B H 0.584105 0.591456 0.058633 0.075 Uiso 1 1 calc R U . . . C9 C 0.8011(8) 0.8314(7) 0.2524(5) 0.060(2) Uani 1 1 d . . . . . H9A H 0.724682 0.851339 0.295997 0.091 Uiso 1 1 calc R U . . . H9B H 0.846415 0.906931 0.230764 0.091 Uiso 1 1 calc R U . . . H9C H 0.873692 0.780008 0.282176 0.091 Uiso 1 1 calc R U . . . C11 C 0.3782(8) 0.6536(7) 0.1851(6) 0.066(2) Uani 1 1 d . . . . . H11 H 0.383090 0.641387 0.121104 0.080 Uiso 1 1 calc R U . . . C13 C 0.2320(9) 0.6920(8) 0.3204(7) 0.077(2) Uani 1 1 d . . . . . H13 H 0.140828 0.705322 0.348058 0.093 Uiso 1 1 calc R U . . . C1 C 0.8323(9) 0.5063(9) 0.3072(6) 0.078(3) Uani 1 1 d . . . . . H1 H 0.894866 0.461051 0.345694 0.094 Uiso 1 1 calc R U . . . C12 C 0.2435(9) 0.6748(9) 0.2270(7) 0.079(3) Uani 1 1 d . . . . . H12 H 0.159064 0.677348 0.190467 0.095 Uiso 1 1 calc R U . . . 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 Br1 0.1003(7) 0.1365(9) 0.0746(6) -0.0019(8) 0.0335(6) 0.0139(7) O1 0.065(3) 0.106(5) 0.062(3) -0.010(3) 0.016(3) -0.027(4) C10 0.049(4) 0.043(4) 0.053(4) 0.007(3) -0.002(3) 0.001(3) C3 0.050(4) 0.045(4) 0.044(4) 0.000(3) -0.002(3) 0.006(3) C15 0.046(4) 0.060(5) 0.056(4) 0.006(4) 0.004(3) -0.001(3) C7 0.046(3) 0.053(5) 0.038(3) -0.001(3) -0.005(3) -0.004(3) C6 0.057(4) 0.072(5) 0.040(3) 0.002(4) -0.002(3) -0.006(5) C14 0.056(4) 0.053(5) 0.071(5) 0.006(4) 0.014(4) 0.003(4) C8 0.075(5) 0.050(5) 0.071(5) 0.009(4) -0.003(4) 0.001(4) C2 0.056(4) 0.062(5) 0.052(4) 0.012(4) 0.013(4) 0.010(4) C5 0.079(6) 0.080(6) 0.052(4) -0.016(4) 0.014(4) 0.001(5) C4 0.074(5) 0.057(5) 0.056(4) -0.009(4) 0.004(4) -0.004(4) C9 0.061(4) 0.072(6) 0.049(4) -0.016(4) 0.003(3) -0.011(4) C11 0.059(5) 0.073(5) 0.067(5) 0.006(4) -0.013(4) -0.003(4) C13 0.060(5) 0.071(6) 0.100(7) 0.005(6) 0.012(5) 0.012(4) C1 0.068(5) 0.093(7) 0.073(6) 0.020(5) 0.010(5) 0.035(5) C12 0.042(4) 0.093(8) 0.103(7) -0.003(6) -0.018(5) 0.002(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Br Br -0.2901 2.4595 '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_ _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 C15 C10 C3 119.0(6) . . ? C11 C10 C3 122.7(6) . . ? C11 C10 C15 118.2(6) . . ? C10 C3 C7 113.5(5) . . ? C10 C3 C4 115.9(6) . . ? C2 C3 C10 109.8(5) . . ? C2 C3 C7 109.0(5) . . ? C2 C3 C4 106.3(6) . . ? C4 C3 C7 101.8(5) . . ? C10 C15 H15 120.3 . . ? C14 C15 C10 119.5(7) . . ? C14 C15 H15 120.3 . . ? C6 C7 C3 102.9(5) . . ? C6 C7 C8 105.9(6) . . ? C6 C7 C9 111.7(5) . . ? C8 C7 C3 111.8(5) . . ? C8 C7 C9 109.1(6) . . ? C9 C7 C3 115.0(5) . . ? O1 C6 C7 124.6(7) . . ? O1 C6 C5 126.1(7) . . ? C5 C6 C7 109.3(6) . . ? C15 C14 Br1 118.6(6) . . ? C13 C14 Br1 119.4(6) . . ? C13 C14 C15 122.0(7) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 C2 C3 177.8(8) . . ? C6 C5 H5A 110.5 . . ? C6 C5 H5B 110.5 . . ? C6 C5 C4 106.1(6) . . ? H5A C5 H5B 108.7 . . ? C4 C5 H5A 110.5 . . ? C4 C5 H5B 110.5 . . ? C3 C4 H4A 110.9 . . ? C3 C4 H4B 110.9 . . ? C5 C4 C3 104.2(6) . . ? C5 C4 H4A 110.9 . . ? C5 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10 C11 H11 119.7 . . ? C10 C11 C12 120.6(8) . . ? C12 C11 H11 119.7 . . ? C14 C13 H13 120.8 . . ? C12 C13 C14 118.4(7) . . ? C12 C13 H13 120.8 . . ? C2 C1 H1 180.0 . . ? C11 C12 H12 119.3 . . ? C13 C12 C11 121.4(8) . . ? C13 C12 H12 119.3 . . ? 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 Br1 C14 1.892(7) . ? O1 C6 1.207(8) . ? C10 C3 1.526(9) . ? C10 C15 1.393(9) . ? C10 C11 1.380(9) . ? C3 C7 1.568(9) . ? C3 C2 1.491(10) . ? C3 C4 1.561(9) . ? C15 H15 0.9300 . ? C15 C14 1.384(9) . ? C7 C6 1.520(9) . ? C7 C8 1.535(9) . ? C7 C9 1.539(9) . ? C6 C5 1.504(11) . ? C14 C13 1.361(11) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C2 C1 1.159(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C4 1.514(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 H11 0.9300 . ? C11 C12 1.383(11) . ? C13 H13 0.9300 . ? C13 C12 1.359(12) . ? C1 H1 0.9300 . ? C12 H12 0.9300 . ? 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 Br1 C14 C13 C12 -179.0(7) . . . . ? O1 C6 C5 C4 -175.5(7) . . . . ? C10 C3 C7 C6 -161.2(5) . . . . ? C10 C3 C7 C8 -48.0(7) . . . . ? C10 C3 C7 C9 77.1(7) . . . . ? C10 C3 C4 C5 162.7(6) . . . . ? C10 C15 C14 Br1 178.8(5) . . . . ? C10 C15 C14 C13 0.4(11) . . . . ? C10 C11 C12 C13 -0.5(14) . . . . ? C3 C10 C15 C14 176.9(6) . . . . ? C3 C10 C11 C12 -176.7(8) . . . . ? C3 C7 C6 O1 -160.1(7) . . . . ? C3 C7 C6 C5 20.6(7) . . . . ? C15 C10 C3 C7 -86.2(7) . . . . ? C15 C10 C3 C2 36.0(9) . . . . ? C15 C10 C3 C4 156.4(6) . . . . ? C15 C10 C11 C12 0.3(11) . . . . ? C15 C14 C13 C12 -0.6(13) . . . . ? C7 C3 C4 C5 38.9(7) . . . . ? C7 C6 C5 C4 3.8(8) . . . . ? C6 C5 C4 C3 -26.8(8) . . . . ? C14 C13 C12 C11 0.7(15) . . . . ? C8 C7 C6 O1 82.4(8) . . . . ? C8 C7 C6 C5 -96.9(7) . . . . ? C2 C3 C7 C6 76.1(6) . . . . ? C2 C3 C7 C8 -170.7(6) . . . . ? C2 C3 C7 C9 -45.5(7) . . . . ? C2 C3 C4 C5 -75.1(7) . . . . ? C4 C3 C7 C6 -35.9(6) . . . . ? C4 C3 C7 C8 77.3(7) . . . . ? C4 C3 C7 C9 -157.6(6) . . . . ? C9 C7 C6 O1 -36.2(10) . . . . ? C9 C7 C6 C5 144.5(6) . . . . ? C11 C10 C3 C7 90.8(8) . . . . ? C11 C10 C3 C2 -147.0(7) . . . . ? C11 C10 C3 C4 -26.6(10) . . . . ? C11 C10 C15 C14 -0.2(10) . . . . ?