#------------------------------------------------------------------------------ #$Date: 2021-03-20 06:25:50 +0200 (Sat, 20 Mar 2021) $ #$Revision: 263197 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060477.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_7060477 loop_ _publ_author_name 'Kukkonen, Esa' 'Lahtinen, Elmeri' 'Myllyperki\"o, Pasi' 'Haukka, Matti' 'Konu, Jari' _publ_section_title ; Nonlinear Optical Properties of Diaromatic Stilbene, Butadiene and Thiophene Derivatives ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ00456E _journal_year 2021 _chemical_formula_moiety 'C32 H28 Cl2 N2 O8' _chemical_formula_sum 'C32 H28 Cl2 N2 O8' _chemical_formula_weight 639.46 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2021-02-26 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-03-10 deposited with the CCDC. 2021-03-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.4671(16) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5166(2) _cell_length_b 12.8669(2) _cell_length_c 19.7897(3) _cell_measurement_reflns_used 5649 _cell_measurement_temperature 120.01(10) _cell_measurement_theta_max 76.3170 _cell_measurement_theta_min 4.1010 _cell_volume 2932.40(8) _computing_cell_refinement 'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1977 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.976 _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 -59.00 27.00 1.00 3.00 -- -41.65 37.00-150.00 86 2 \w -96.00 -4.00 1.00 3.00 -- -41.65 125.00 -90.00 92 3 \w 4.00 77.00 1.00 3.00 -- 41.65 -99.00 120.00 73 4 \w 88.00 177.00 1.00 10.00 -- 112.00 45.00 -30.00 89 5 \w 29.00 102.00 1.00 10.00 -- 112.00 -94.00 90.00 73 6 \w 55.00 138.00 1.00 10.00 -- 112.00 -45.00-120.00 83 7 \w 101.00 174.00 1.00 10.00 -- 112.00 15.00-120.00 73 8 \w 63.00 90.00 1.00 10.00 -- 112.00 15.00-120.00 27 9 \w 40.00 138.00 1.00 10.00 -- 112.00 -45.00 150.00 98 10 \w 65.00 103.00 1.00 10.00 -- 112.00 -94.00 -30.00 38 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0739749000 _diffrn_orient_matrix_UB_12 -0.0549485000 _diffrn_orient_matrix_UB_13 0.0537253000 _diffrn_orient_matrix_UB_21 -0.0551511000 _diffrn_orient_matrix_UB_22 -0.0687214000 _diffrn_orient_matrix_UB_23 -0.0553669000 _diffrn_orient_matrix_UB_31 0.0968187000 _diffrn_orient_matrix_UB_32 -0.0812427000 _diffrn_orient_matrix_UB_33 0.0104033000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12694 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.512 _diffrn_reflns_theta_min 4.098 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.476 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75477 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.448 _exptl_crystal_description block _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.304 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 6015 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0356 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.7892P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0901 _refine_ls_wR_factor_ref 0.0958 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5148 _reflns_number_total 6015 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj00456e2.cif _cod_data_source_block compound_4_Pcell _cod_original_cell_volume 2932.40(9) _cod_database_code 7060477 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C14 H14 O4 N1 Cl1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.886 _shelx_estimated_absorpt_t_min 0.576 _reflns_odcompleteness_completeness 98.98 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C7(H7), C8(H8), C23(H23), C24(H24) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C18(H18), C19(H19), C21(H21), C22(H22), C26(H26), C27(H27) 2.c Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C31(H31A,H31B,H31C), C32(H32A,H32B, H32C) ; _shelx_res_file ; TITL ek1912 in P21/n #14 ek1912.res created by SHELXL-2018/3 at 10:47:20 on 26-Feb-2021 REM reset to P21/n #14 CELL 1.54184 11.516591 12.866887 19.789742 90 90.4671 90 ZERR 4 0.000238 0.000247 0.000297 0 0.0016 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 128 112 8 8 32 EQIV $1 1.5-X,0.5+Y,0.5-Z EQIV $2 1-X,3-Y,-Z EQIV $3 0.5+X,2.5-Y,0.5+Z EQIV $4 1-X,2-Y,1-Z EQIV $5 2-X,2-Y,1-Z L.S. 4 PLAN 2 SIZE 0.25 0.1 0.05 HTAB C5 O4_$1 HTAB C6 O2_$2 HTAB C13 O1_$3 HTAB C15 O1_$3 HTAB C15 O4_$4 HTAB C15 O5_$5 BOND $H CONF fmap 2 53 acta REM REM REM WGHT 0.047700 0.789200 FVAR 3.09324 CL1 3 0.599539 0.801385 0.192077 11.00000 0.03699 0.01881 = 0.02044 -0.00363 -0.00127 -0.00401 CL2 3 0.933057 1.204728 -0.020027 11.00000 0.03260 0.02803 = 0.03078 0.00831 -0.00133 -0.00391 O1 5 0.350159 1.296618 -0.055746 11.00000 0.03632 0.03388 = 0.02945 -0.00483 -0.01264 0.00960 O2 5 0.467203 1.427608 -0.057106 11.00000 0.05676 0.03162 = 0.06254 0.02163 -0.01767 0.00280 O3 5 0.543061 0.806644 0.334935 11.00000 0.02835 0.02246 = 0.02508 0.00252 0.00348 -0.00201 O4 5 0.590602 0.959790 0.423187 11.00000 0.03171 0.03207 = 0.01699 -0.00311 0.00154 -0.00501 O5 5 1.208194 1.009371 0.379366 11.00000 0.05438 0.04626 = 0.04365 0.00095 -0.02569 0.00062 O6 5 1.154248 0.851387 0.397405 11.00000 0.04070 0.05621 = 0.03171 0.02298 -0.00645 0.00331 O7 5 0.827881 1.164140 -0.152003 11.00000 0.03406 0.04138 = 0.02270 0.01205 0.00620 0.00666 O8 5 0.701202 1.000215 -0.189082 11.00000 0.04040 0.04997 = 0.01914 -0.00113 -0.00337 0.00366 N1 4 0.442743 1.338576 -0.041106 11.00000 0.03789 0.02564 = 0.02329 0.00181 -0.00394 0.00882 N2 4 1.148856 0.933303 0.365698 11.00000 0.03228 0.04405 = 0.02314 0.00688 -0.00333 0.00763 C1 1 0.527833 1.278672 -0.001828 11.00000 0.02762 0.02468 = 0.02020 0.00286 -0.00101 0.00649 C2 1 0.514139 1.172486 0.000997 11.00000 0.02980 0.02416 = 0.02634 -0.00237 -0.00693 0.00199 AFIX 43 H2 2 0.454056 1.140065 -0.022561 11.00000 -1.20000 AFIX 0 C3 1 0.591407 1.115033 0.039515 11.00000 0.03272 0.01758 = 0.03076 -0.00126 -0.00787 0.00175 AFIX 43 H3 2 0.583103 1.043204 0.041483 11.00000 -1.20000 AFIX 0 C4 1 0.681422 1.162269 0.075450 11.00000 0.02464 0.01869 = 0.01864 0.00108 0.00049 0.00307 C5 1 0.692769 1.269830 0.070733 11.00000 0.03115 0.02137 = 0.03497 0.00188 -0.00918 -0.00135 AFIX 43 H5 2 0.752703 1.302746 0.094127 11.00000 -1.20000 AFIX 0 C6 1 0.616769 1.328886 0.031970 11.00000 0.03890 0.01829 = 0.04170 0.00610 -0.00877 -0.00067 AFIX 43 H6 2 0.625516 1.400572 0.028825 11.00000 -1.20000 AFIX 0 C7 1 0.767525 1.100432 0.116850 11.00000 0.02399 0.01992 = 0.01735 0.00085 -0.00167 0.00080 AFIX 13 H7 2 0.801294 1.145071 0.151993 11.00000 -1.20000 AFIX 0 C8 1 0.727328 0.997214 0.148846 11.00000 0.02434 0.01754 = 0.01719 0.00019 -0.00263 0.00119 AFIX 13 H8 2 0.668854 0.965307 0.119173 11.00000 -1.20000 AFIX 0 C9 1 0.684218 0.993957 0.220321 11.00000 0.02122 0.01941 = 0.01728 -0.00026 -0.00262 0.00238 C10 1 0.626831 0.906284 0.245252 11.00000 0.02189 0.01816 = 0.01840 -0.00257 -0.00313 0.00193 C11 1 0.592947 0.896765 0.312344 11.00000 0.02288 0.01910 = 0.02010 0.00140 -0.00118 0.00049 C12 1 0.619521 0.977978 0.357681 11.00000 0.02346 0.02615 = 0.01671 -0.00221 0.00006 0.00159 C13 1 0.674313 1.066402 0.334084 11.00000 0.03063 0.02372 = 0.02131 -0.00553 -0.00178 -0.00106 AFIX 43 H13 2 0.690278 1.121089 0.363449 11.00000 -1.20000 AFIX 0 C14 1 0.705647 1.073586 0.266225 11.00000 0.02884 0.01827 = 0.02276 -0.00134 -0.00126 -0.00282 AFIX 43 H14 2 0.742105 1.133712 0.251229 11.00000 -1.20000 AFIX 0 C15 1 0.634722 1.031728 0.472462 11.00000 0.03618 0.04424 = 0.01961 -0.00830 0.00021 -0.00674 AFIX 137 H15A 2 0.597031 1.097728 0.466742 11.00000 -1.50000 H15B 2 0.716879 1.039961 0.466621 11.00000 -1.50000 H15C 2 0.619782 1.005638 0.516999 11.00000 -1.50000 AFIX 0 C16 1 0.421583 0.816218 0.349044 11.00000 0.02999 0.03350 = 0.03854 -0.00259 0.00663 -0.00672 AFIX 137 H16A 2 0.379818 0.830037 0.307836 11.00000 -1.50000 H16B 2 0.409759 0.872357 0.380190 11.00000 -1.50000 H16C 2 0.393855 0.752668 0.368549 11.00000 -1.50000 AFIX 0 C17 1 1.068729 0.939264 0.307508 11.00000 0.02755 0.03500 = 0.01961 0.00451 -0.00207 0.00731 C18 1 1.004626 0.852753 0.289718 11.00000 0.03224 0.03019 = 0.02412 0.01015 0.00105 0.00594 AFIX 43 H18 2 1.007701 0.792616 0.315741 11.00000 -1.20000 AFIX 0 C19 1 0.935435 0.857643 0.232042 11.00000 0.02908 0.02288 = 0.02552 0.00461 0.00047 0.00217 AFIX 43 H19 2 0.892054 0.799869 0.219182 11.00000 -1.20000 AFIX 0 C20 1 0.929960 0.947990 0.193026 11.00000 0.02402 0.02315 = 0.01950 0.00298 0.00146 0.00573 C21 1 0.992707 1.034650 0.214181 11.00000 0.03080 0.02319 = 0.02472 0.00543 -0.00347 0.00336 AFIX 43 H21 2 0.987472 1.096054 0.189553 11.00000 -1.20000 AFIX 0 C22 1 1.062935 1.030953 0.271398 11.00000 0.02986 0.02869 = 0.02672 0.00142 -0.00503 0.00216 AFIX 43 H22 2 1.105173 1.088933 0.285133 11.00000 -1.20000 AFIX 0 C23 1 0.850088 0.948485 0.132408 11.00000 0.02644 0.01843 = 0.01941 0.00088 0.00028 0.00274 AFIX 13 H23 2 0.843925 0.880058 0.110929 11.00000 -1.20000 AFIX 0 C24 1 0.868694 1.037185 0.080476 11.00000 0.02392 0.02063 = 0.02003 0.00342 -0.00056 0.00137 AFIX 13 H24 2 0.944646 1.070714 0.085691 11.00000 -1.20000 AFIX 0 C25 1 0.838676 1.014930 0.007633 11.00000 0.02264 0.02445 = 0.01912 0.00276 0.00189 0.00464 C26 1 0.781542 0.926184 -0.014290 11.00000 0.02968 0.02407 = 0.02181 0.00131 0.00150 0.00434 AFIX 43 H26 2 0.772828 0.871159 0.015716 11.00000 -1.20000 AFIX 0 C27 1 0.736484 0.916195 -0.079810 11.00000 0.03068 0.02860 = 0.02380 -0.00523 0.00015 0.00323 AFIX 43 H27 2 0.699109 0.855258 -0.092859 11.00000 -1.20000 AFIX 0 C28 1 0.747778 0.997467 -0.125175 11.00000 0.02974 0.03982 = 0.01650 -0.00253 0.00034 0.00787 C29 1 0.810690 1.086148 -0.106194 11.00000 0.02712 0.03495 = 0.01987 0.00589 0.00525 0.00712 C30 1 0.856149 1.092913 -0.041000 11.00000 0.02312 0.02635 = 0.02217 0.00188 0.00276 0.00375 C31 1 0.738434 1.241784 -0.150029 11.00000 0.04761 0.04805 = 0.04286 0.02287 0.00819 0.01499 AFIX 137 H31A 2 0.756569 1.296542 -0.181157 11.00000 -1.50000 H31B 2 0.733536 1.269727 -0.105164 11.00000 -1.50000 H31C 2 0.665389 1.210998 -0.162448 11.00000 -1.50000 AFIX 0 C32 1 0.626625 0.916057 -0.207134 11.00000 0.04378 0.05397 = 0.02759 -0.01113 -0.00863 0.00619 AFIX 137 H32A 2 0.595909 0.927255 -0.251785 11.00000 -1.50000 H32B 2 0.563912 0.911986 -0.175582 11.00000 -1.50000 H32C 2 0.669840 0.852266 -0.206189 11.00000 -1.50000 AFIX 0 HKLF 4 REM ek1912 in P21/n #14 REM wR2 = 0.0958, GooF = S = 1.021, Restrained GooF = 1.021 for all data REM R1 = 0.0356 for 5148 Fo > 4sig(Fo) and 0.0429 for all 6015 data REM 401 parameters refined using 0 restraints END WGHT 0.0477 0.7892 REM Highest difference peak 0.304, deepest hole -0.254, 1-sigma level 0.048 Q1 1 0.7048 1.0004 0.1862 11.00000 0.05 0.30 Q2 1 0.6022 0.9032 0.2811 11.00000 0.05 0.29 ; _shelx_res_checksum 3867 _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 1.406 _oxdiff_exptl_absorpt_empirical_full_min 0.798 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 Cl1 Cl 0.59954(3) 0.80138(3) 0.19208(2) 0.02542(10) Uani 1 1 d . . . . . Cl2 Cl 0.93306(4) 1.20473(3) -0.02003(2) 0.03048(10) Uani 1 1 d . . . . . O1 O 0.35016(11) 1.29662(10) -0.05575(6) 0.0333(3) Uani 1 1 d . . . . . O2 O 0.46720(14) 1.42761(12) -0.05711(8) 0.0504(4) Uani 1 1 d . . . . . O3 O 0.54306(10) 0.80664(9) 0.33494(6) 0.0253(2) Uani 1 1 d . . . . . O4 O 0.59060(10) 0.95979(9) 0.42319(5) 0.0269(2) Uani 1 1 d . . . . . O5 O 1.20819(14) 1.00937(12) 0.37937(8) 0.0482(4) Uani 1 1 d . . . . . O6 O 1.15425(12) 0.85139(13) 0.39740(7) 0.0429(3) Uani 1 1 d . . . . . O7 O 0.82788(11) 1.16414(11) -0.15200(6) 0.0327(3) Uani 1 1 d . . . . . O8 O 0.70120(12) 1.00022(11) -0.18908(6) 0.0365(3) Uani 1 1 d . . . . . N1 N 0.44274(13) 1.33858(11) -0.04111(7) 0.0290(3) Uani 1 1 d . . . . . N2 N 1.14886(13) 0.93330(13) 0.36570(7) 0.0332(3) Uani 1 1 d . . . . . C1 C 0.52783(14) 1.27867(12) -0.00183(8) 0.0242(3) Uani 1 1 d . . . . . C2 C 0.51414(15) 1.17249(13) 0.00100(8) 0.0268(3) Uani 1 1 d . . . . . H2 H 0.454056 1.140065 -0.022561 0.032 Uiso 1 1 calc R . . . . C3 C 0.59141(15) 1.11503(12) 0.03952(8) 0.0271(3) Uani 1 1 d . . . . . H3 H 0.583103 1.043204 0.041483 0.032 Uiso 1 1 calc R . . . . C4 C 0.68142(13) 1.16227(12) 0.07545(7) 0.0207(3) Uani 1 1 d . . . . . C5 C 0.69277(15) 1.26983(13) 0.07073(9) 0.0292(3) Uani 1 1 d . . . . . H5 H 0.752703 1.302746 0.094127 0.035 Uiso 1 1 calc R . . . . C6 C 0.61677(16) 1.32889(13) 0.03197(9) 0.0330(4) Uani 1 1 d . . . . . H6 H 0.625516 1.400572 0.028825 0.040 Uiso 1 1 calc R . . . . C7 C 0.76753(13) 1.10043(12) 0.11685(7) 0.0204(3) Uani 1 1 d . . . . . H7 H 0.801294 1.145071 0.151993 0.025 Uiso 1 1 calc R . . . . C8 C 0.72733(13) 0.99721(11) 0.14885(7) 0.0197(3) Uani 1 1 d . . . . . H8 H 0.668854 0.965307 0.119173 0.024 Uiso 1 1 calc R . . . . C9 C 0.68422(13) 0.99396(12) 0.22032(7) 0.0193(3) Uani 1 1 d . . . . . C10 C 0.62683(13) 0.90628(11) 0.24525(7) 0.0195(3) Uani 1 1 d . . . . . C11 C 0.59295(13) 0.89676(12) 0.31234(7) 0.0207(3) Uani 1 1 d . . . . . C12 C 0.61952(13) 0.97798(12) 0.35768(7) 0.0221(3) Uani 1 1 d . . . . . C13 C 0.67431(14) 1.06640(13) 0.33408(8) 0.0252(3) Uani 1 1 d . . . . . H13 H 0.690278 1.121089 0.363449 0.030 Uiso 1 1 calc R . . . . C14 C 0.70565(14) 1.07359(12) 0.26622(8) 0.0233(3) Uani 1 1 d . . . . . H14 H 0.742105 1.133712 0.251229 0.028 Uiso 1 1 calc R . . . . C15 C 0.63472(16) 1.03173(16) 0.47246(8) 0.0333(4) Uani 1 1 d . . . . . H15A H 0.597031 1.097728 0.466742 0.050 Uiso 1 1 calc GR . . . . H15B H 0.716879 1.039961 0.466621 0.050 Uiso 1 1 calc GR . . . . H15C H 0.619782 1.005638 0.516999 0.050 Uiso 1 1 calc GR . . . . C16 C 0.42158(16) 0.81622(15) 0.34904(10) 0.0340(4) Uani 1 1 d . . . . . H16A H 0.379818 0.830037 0.307836 0.051 Uiso 1 1 calc GR . . . . H16B H 0.409759 0.872357 0.380190 0.051 Uiso 1 1 calc GR . . . . H16C H 0.393855 0.752668 0.368549 0.051 Uiso 1 1 calc GR . . . . C17 C 1.06873(15) 0.93926(14) 0.30751(8) 0.0274(3) Uani 1 1 d . . . . . C18 C 1.00463(15) 0.85275(14) 0.28972(8) 0.0288(3) Uani 1 1 d . . . . . H18 H 1.007701 0.792616 0.315741 0.035 Uiso 1 1 calc R . . . . C19 C 0.93543(14) 0.85764(13) 0.23204(8) 0.0258(3) Uani 1 1 d . . . . . H19 H 0.892054 0.799869 0.219182 0.031 Uiso 1 1 calc R . . . . C20 C 0.92996(14) 0.94799(12) 0.19303(7) 0.0222(3) Uani 1 1 d . . . . . C21 C 0.99271(14) 1.03465(13) 0.21418(8) 0.0263(3) Uani 1 1 d . . . . . H21 H 0.987472 1.096054 0.189553 0.032 Uiso 1 1 calc R . . . . C22 C 1.06293(15) 1.03095(14) 0.27140(8) 0.0285(3) Uani 1 1 d . . . . . H22 H 1.105173 1.088933 0.285133 0.034 Uiso 1 1 calc R . . . . C23 C 0.85009(13) 0.94848(12) 0.13241(7) 0.0214(3) Uani 1 1 d . . . . . H23 H 0.843925 0.880058 0.110929 0.026 Uiso 1 1 calc R . . . . C24 C 0.86869(13) 1.03718(12) 0.08048(7) 0.0215(3) Uani 1 1 d . . . . . H24 H 0.944646 1.070714 0.085691 0.026 Uiso 1 1 calc R . . . . C25 C 0.83868(13) 1.01493(12) 0.00763(7) 0.0221(3) Uani 1 1 d . . . . . C26 C 0.78154(14) 0.92618(13) -0.01429(8) 0.0252(3) Uani 1 1 d . . . . . H26 H 0.772828 0.871159 0.015716 0.030 Uiso 1 1 calc R . . . . C27 C 0.73648(15) 0.91619(14) -0.07981(8) 0.0277(3) Uani 1 1 d . . . . . H27 H 0.699109 0.855258 -0.092859 0.033 Uiso 1 1 calc R . . . . C28 C 0.74778(15) 0.99747(15) -0.12517(8) 0.0287(3) Uani 1 1 d . . . . . C29 C 0.81069(14) 1.08615(14) -0.10619(8) 0.0273(3) Uani 1 1 d . . . . . C30 C 0.85615(14) 1.09291(13) -0.04100(8) 0.0239(3) Uani 1 1 d . . . . . C31 C 0.73843(19) 1.24178(18) -0.15003(11) 0.0461(5) Uani 1 1 d . . . . . H31A H 0.756569 1.296542 -0.181157 0.069 Uiso 1 1 calc GR . . . . H31B H 0.733536 1.269727 -0.105164 0.069 Uiso 1 1 calc GR . . . . H31C H 0.665389 1.210998 -0.162448 0.069 Uiso 1 1 calc GR . . . . C32 C 0.62662(18) 0.91606(18) -0.20713(9) 0.0418(5) Uani 1 1 d . . . . . H32A H 0.595909 0.927255 -0.251785 0.063 Uiso 1 1 calc GR . . . . H32B H 0.563912 0.911986 -0.175582 0.063 Uiso 1 1 calc GR . . . . H32C H 0.669840 0.852266 -0.206189 0.063 Uiso 1 1 calc GR . . . . 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 Cl1 0.0370(2) 0.01881(17) 0.02044(17) -0.00363(12) -0.00127(14) -0.00401(14) Cl2 0.0326(2) 0.0280(2) 0.03078(19) 0.00831(15) -0.00133(15) -0.00391(15) O1 0.0363(7) 0.0339(7) 0.0295(6) -0.0048(5) -0.0126(5) 0.0096(5) O2 0.0568(9) 0.0316(7) 0.0625(9) 0.0216(7) -0.0177(7) 0.0028(6) O3 0.0284(6) 0.0225(5) 0.0251(5) 0.0025(4) 0.0035(4) -0.0020(4) O4 0.0317(6) 0.0321(6) 0.0170(5) -0.0031(4) 0.0015(4) -0.0050(5) O5 0.0544(9) 0.0463(9) 0.0437(8) 0.0009(6) -0.0257(7) 0.0006(7) O6 0.0407(7) 0.0562(9) 0.0317(7) 0.0230(6) -0.0064(5) 0.0033(6) O7 0.0341(6) 0.0414(7) 0.0227(5) 0.0121(5) 0.0062(5) 0.0067(5) O8 0.0404(7) 0.0500(8) 0.0191(5) -0.0011(5) -0.0034(5) 0.0037(6) N1 0.0379(8) 0.0256(7) 0.0233(6) 0.0018(5) -0.0039(6) 0.0088(6) N2 0.0323(8) 0.0441(9) 0.0231(7) 0.0069(6) -0.0033(6) 0.0076(7) C1 0.0276(8) 0.0247(8) 0.0202(7) 0.0029(6) -0.0010(6) 0.0065(6) C2 0.0298(8) 0.0242(8) 0.0263(7) -0.0024(6) -0.0069(6) 0.0020(6) C3 0.0327(9) 0.0176(7) 0.0308(8) -0.0013(6) -0.0079(7) 0.0017(6) C4 0.0246(7) 0.0187(7) 0.0186(6) 0.0011(5) 0.0005(5) 0.0031(6) C5 0.0311(9) 0.0214(8) 0.0350(8) 0.0019(6) -0.0092(7) -0.0014(6) C6 0.0389(10) 0.0183(8) 0.0417(9) 0.0061(7) -0.0088(8) -0.0007(7) C7 0.0240(7) 0.0199(7) 0.0173(6) 0.0009(5) -0.0017(5) 0.0008(6) C8 0.0243(7) 0.0175(7) 0.0172(6) 0.0002(5) -0.0026(5) 0.0012(5) C9 0.0212(7) 0.0194(7) 0.0173(6) -0.0003(5) -0.0026(5) 0.0024(5) C10 0.0219(7) 0.0182(7) 0.0184(6) -0.0026(5) -0.0031(5) 0.0019(5) C11 0.0229(7) 0.0191(7) 0.0201(7) 0.0014(5) -0.0012(5) 0.0005(5) C12 0.0235(7) 0.0262(8) 0.0167(6) -0.0022(6) 0.0001(5) 0.0016(6) C13 0.0306(8) 0.0237(7) 0.0213(7) -0.0055(6) -0.0018(6) -0.0011(6) C14 0.0288(8) 0.0183(7) 0.0228(7) -0.0013(6) -0.0013(6) -0.0028(6) C15 0.0362(9) 0.0442(10) 0.0196(7) -0.0083(7) 0.0002(6) -0.0067(8) C16 0.0300(9) 0.0335(9) 0.0385(9) -0.0026(7) 0.0066(7) -0.0067(7) C17 0.0276(8) 0.0350(9) 0.0196(7) 0.0045(6) -0.0021(6) 0.0073(7) C18 0.0322(9) 0.0302(8) 0.0241(7) 0.0101(6) 0.0010(6) 0.0059(7) C19 0.0291(8) 0.0229(7) 0.0255(7) 0.0046(6) 0.0005(6) 0.0022(6) C20 0.0240(7) 0.0231(7) 0.0195(7) 0.0030(6) 0.0015(5) 0.0057(6) C21 0.0308(8) 0.0232(8) 0.0247(7) 0.0054(6) -0.0035(6) 0.0034(6) C22 0.0299(8) 0.0287(8) 0.0267(8) 0.0014(6) -0.0050(6) 0.0022(6) C23 0.0264(8) 0.0184(7) 0.0194(7) 0.0009(5) 0.0003(6) 0.0027(6) C24 0.0239(7) 0.0206(7) 0.0200(7) 0.0034(6) -0.0006(5) 0.0014(6) C25 0.0226(7) 0.0245(7) 0.0191(7) 0.0028(6) 0.0019(5) 0.0046(6) C26 0.0297(8) 0.0241(8) 0.0218(7) 0.0013(6) 0.0015(6) 0.0043(6) C27 0.0307(8) 0.0286(8) 0.0238(7) -0.0052(6) 0.0002(6) 0.0032(6) C28 0.0297(8) 0.0398(9) 0.0165(7) -0.0025(6) 0.0003(6) 0.0079(7) C29 0.0271(8) 0.0350(9) 0.0199(7) 0.0059(6) 0.0052(6) 0.0071(7) C30 0.0231(7) 0.0264(8) 0.0222(7) 0.0019(6) 0.0028(6) 0.0037(6) C31 0.0476(12) 0.0480(12) 0.0429(11) 0.0229(9) 0.0082(9) 0.0150(10) C32 0.0438(11) 0.0540(12) 0.0276(9) -0.0111(8) -0.0086(8) 0.0062(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _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 C11 O3 C16 113.76(13) . . ? C12 O4 C15 116.64(13) . . ? C29 O7 C31 112.63(13) . . ? C28 O8 C32 116.24(15) . . ? O1 N1 C1 118.02(14) . . ? O2 N1 O1 123.55(15) . . ? O2 N1 C1 118.43(15) . . ? O5 N2 O6 123.24(15) . . ? O5 N2 C17 118.49(15) . . ? O6 N2 C17 118.25(16) . . ? C2 C1 N1 117.87(15) . . ? C2 C1 C6 122.01(15) . . ? C6 C1 N1 120.11(15) . . ? C1 C2 H2 120.7 . . ? C1 C2 C3 118.69(15) . . ? C3 C2 H2 120.7 . . ? C2 C3 H3 119.3 . . ? C2 C3 C4 121.46(15) . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 117.99(14) . . ? C3 C4 C7 122.06(14) . . ? C5 C4 C7 119.92(14) . . ? C4 C5 H5 119.3 . . ? C6 C5 C4 121.50(16) . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.34(16) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C4 C7 H7 109.4 . . ? C4 C7 C8 118.59(13) . . ? C4 C7 C24 120.18(12) . . ? C8 C7 H7 109.4 . . ? C8 C7 C24 88.21(11) . . ? C24 C7 H7 109.4 . . ? C7 C8 H8 108.8 . . ? C7 C8 C23 89.15(11) . . ? C9 C8 C7 120.81(12) . . ? C9 C8 H8 108.8 . . ? C9 C8 C23 118.99(12) . . ? C23 C8 H8 108.8 . . ? C10 C9 C8 120.98(13) . . ? C14 C9 C8 122.42(14) . . ? C14 C9 C10 116.46(13) . . ? C9 C10 Cl1 119.74(11) . . ? C11 C10 Cl1 117.27(12) . . ? C11 C10 C9 122.96(13) . . ? O3 C11 C10 120.46(13) . . ? O3 C11 C12 120.60(13) . . ? C10 C11 C12 118.74(14) . . ? O4 C12 C11 115.17(14) . . ? O4 C12 C13 125.34(14) . . ? C13 C12 C11 119.47(14) . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 120.07(14) . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 122.26(15) . . ? C9 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N2 119.23(15) . . ? C18 C17 C22 122.26(15) . . ? C22 C17 N2 118.48(16) . . ? C17 C18 H18 120.8 . . ? C17 C18 C19 118.40(15) . . ? C19 C18 H18 120.8 . . ? C18 C19 H19 119.5 . . ? C18 C19 C20 121.02(16) . . ? C20 C19 H19 119.5 . . ? C19 C20 C23 117.94(14) . . ? C21 C20 C19 118.67(14) . . ? C21 C20 C23 123.28(14) . . ? C20 C21 H21 119.5 . . ? C22 C21 C20 121.07(15) . . ? C22 C21 H21 119.5 . . ? C17 C22 C21 118.51(16) . . ? C17 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C8 C23 H23 112.5 . . ? C20 C23 C8 112.26(12) . . ? C20 C23 H23 112.5 . . ? C20 C23 C24 116.36(13) . . ? C24 C23 C8 88.46(11) . . ? C24 C23 H23 112.5 . . ? C7 C24 H24 112.5 . . ? C23 C24 C7 88.34(11) . . ? C23 C24 H24 112.5 . . ? C25 C24 C7 111.43(12) . . ? C25 C24 C23 117.51(13) . . ? C25 C24 H24 112.5 . . ? C26 C25 C24 124.10(14) . . ? C26 C25 C30 116.36(14) . . ? C30 C25 C24 119.09(14) . . ? C25 C26 H26 118.7 . . ? C25 C26 C27 122.52(15) . . ? C27 C26 H26 118.7 . . ? C26 C27 H27 120.2 . . ? C28 C27 C26 119.70(16) . . ? C28 C27 H27 120.2 . . ? O8 C28 C27 125.43(17) . . ? O8 C28 C29 115.09(15) . . ? C27 C28 C29 119.48(15) . . ? O7 C29 C28 119.81(15) . . ? O7 C29 C30 120.89(16) . . ? C30 C29 C28 119.30(15) . . ? C25 C30 Cl2 120.19(12) . . ? C29 C30 Cl2 117.42(13) . . ? C29 C30 C25 122.37(15) . . ? O7 C31 H31A 109.5 . . ? O7 C31 H31B 109.5 . . ? O7 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O8 C32 H32A 109.5 . . ? O8 C32 H32B 109.5 . . ? O8 C32 H32C 109.5 . . ? H32A C32 H32B 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 Cl1 C10 1.7386(15) . ? Cl2 C30 1.7380(17) . ? O1 N1 1.228(2) . ? O2 N1 1.222(2) . ? O3 C11 1.3707(19) . ? O3 C16 1.434(2) . ? O4 C12 1.3613(18) . ? O4 C15 1.434(2) . ? O5 N2 1.223(2) . ? O6 N2 1.228(2) . ? O7 C29 1.368(2) . ? O7 C31 1.436(2) . ? O8 C28 1.3702(19) . ? O8 C32 1.426(3) . ? N1 C1 1.465(2) . ? N2 C17 1.472(2) . ? C1 C2 1.377(2) . ? C1 C6 1.379(2) . ? C2 H2 0.9300 . ? C2 C3 1.381(2) . ? C3 H3 0.9300 . ? C3 C4 1.392(2) . ? C4 C5 1.393(2) . ? C4 C7 1.508(2) . ? C5 H5 0.9300 . ? C5 C6 1.386(2) . ? C6 H6 0.9300 . ? C7 H7 0.9800 . ? C7 C8 1.544(2) . ? C7 C24 1.597(2) . ? C8 H8 0.9800 . ? C8 C9 1.5035(19) . ? C8 C23 1.583(2) . ? C9 C10 1.399(2) . ? C9 C14 1.390(2) . ? C10 C11 1.392(2) . ? C11 C12 1.409(2) . ? C12 C13 1.384(2) . ? C13 H13 0.9300 . ? C13 C14 1.396(2) . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.380(3) . ? C17 C22 1.381(2) . ? C18 H18 0.9300 . ? C18 C19 1.388(2) . ? C19 H19 0.9300 . ? C19 C20 1.397(2) . ? C20 C21 1.391(2) . ? C20 C23 1.506(2) . ? C21 H21 0.9300 . ? C21 C22 1.387(2) . ? C22 H22 0.9300 . ? C23 H23 0.9800 . ? C23 C24 1.552(2) . ? C24 H24 0.9800 . ? C24 C25 1.507(2) . ? C25 C26 1.386(2) . ? C25 C30 1.406(2) . ? C26 H26 0.9300 . ? C26 C27 1.399(2) . ? C27 H27 0.9300 . ? C27 C28 1.385(2) . ? C28 C29 1.401(3) . ? C29 C30 1.391(2) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C6 H6 O2 0.93 2.52 3.318(2) 144.0 3_685 yes 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 Cl1 C10 C11 O3 1.68(19) . . . . ? Cl1 C10 C11 C12 176.53(11) . . . . ? O1 N1 C1 C2 17.1(2) . . . . ? O1 N1 C1 C6 -161.63(16) . . . . ? O2 N1 C1 C2 -163.43(17) . . . . ? O2 N1 C1 C6 17.9(2) . . . . ? O3 C11 C12 O4 -0.9(2) . . . . ? O3 C11 C12 C13 177.30(14) . . . . ? O4 C12 C13 C14 176.26(15) . . . . ? O5 N2 C17 C18 177.38(17) . . . . ? O5 N2 C17 C22 -0.8(2) . . . . ? O6 N2 C17 C18 -1.3(2) . . . . ? O6 N2 C17 C22 -179.55(16) . . . . ? O7 C29 C30 Cl2 1.0(2) . . . . ? O7 C29 C30 C25 179.03(14) . . . . ? O8 C28 C29 O7 -4.1(2) . . . . ? O8 C28 C29 C30 176.67(14) . . . . ? N1 C1 C2 C3 -178.00(15) . . . . ? N1 C1 C6 C5 177.48(16) . . . . ? N2 C17 C18 C19 -175.73(15) . . . . ? N2 C17 C22 C21 176.19(15) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C1 C6 C5 -1.2(3) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C2 C3 C4 C7 -179.04(15) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C3 C4 C7 C8 -30.0(2) . . . . ? C3 C4 C7 C24 76.05(19) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C4 C7 C8 C9 -94.56(16) . . . . ? C4 C7 C8 C23 141.69(13) . . . . ? C4 C7 C24 C23 -140.69(14) . . . . ? C4 C7 C24 C25 -21.68(19) . . . . ? C5 C4 C7 C8 151.97(15) . . . . ? C5 C4 C7 C24 -102.01(17) . . . . ? C6 C1 C2 C3 0.7(3) . . . . ? C7 C4 C5 C6 178.58(16) . . . . ? C7 C8 C9 C10 167.34(13) . . . . ? C7 C8 C9 C14 -17.1(2) . . . . ? C7 C8 C23 C20 99.50(13) . . . . ? C7 C8 C23 C24 -18.46(11) . . . . ? C7 C24 C25 C26 -90.73(18) . . . . ? C7 C24 C25 C30 81.25(17) . . . . ? C8 C7 C24 C23 -18.30(11) . . . . ? C8 C7 C24 C25 100.72(13) . . . . ? C8 C9 C10 Cl1 -2.61(19) . . . . ? C8 C9 C10 C11 175.19(14) . . . . ? C8 C9 C14 C13 -174.31(15) . . . . ? C8 C23 C24 C7 17.83(10) . . . . ? C8 C23 C24 C25 -95.56(14) . . . . ? C9 C8 C23 C20 -25.77(18) . . . . ? C9 C8 C23 C24 -143.73(13) . . . . ? C9 C10 C11 O3 -176.17(14) . . . . ? C9 C10 C11 C12 -1.3(2) . . . . ? C10 C9 C14 C13 1.4(2) . . . . ? C10 C11 C12 O4 -175.72(13) . . . . ? C10 C11 C12 C13 2.5(2) . . . . ? C11 C12 C13 C14 -1.7(2) . . . . ? C12 C13 C14 C9 -0.3(3) . . . . ? C14 C9 C10 Cl1 -178.38(11) . . . . ? C14 C9 C10 C11 -0.6(2) . . . . ? C15 O4 C12 C11 169.11(14) . . . . ? C15 O4 C12 C13 -8.9(2) . . . . ? C16 O3 C11 C10 -108.88(16) . . . . ? C16 O3 C11 C12 76.37(18) . . . . ? C17 C18 C19 C20 -0.4(2) . . . . ? C18 C17 C22 C21 -2.0(3) . . . . ? C18 C19 C20 C21 -1.9(2) . . . . ? C18 C19 C20 C23 -178.11(15) . . . . ? C19 C20 C21 C22 2.4(2) . . . . ? C19 C20 C23 C8 95.26(16) . . . . ? C19 C20 C23 C24 -164.92(14) . . . . ? C20 C21 C22 C17 -0.5(3) . . . . ? C20 C23 C24 C7 -96.35(14) . . . . ? C20 C23 C24 C25 150.26(13) . . . . ? C21 C20 C23 C8 -80.73(18) . . . . ? C21 C20 C23 C24 19.1(2) . . . . ? C22 C17 C18 C19 2.4(3) . . . . ? C23 C8 C9 C10 -84.56(18) . . . . ? C23 C8 C9 C14 90.96(18) . . . . ? C23 C20 C21 C22 178.36(15) . . . . ? C23 C24 C25 C26 9.0(2) . . . . ? C23 C24 C25 C30 -179.00(14) . . . . ? C24 C7 C8 C9 141.67(13) . . . . ? C24 C7 C8 C23 17.92(10) . . . . ? C24 C25 C26 C27 168.13(15) . . . . ? C24 C25 C30 Cl2 10.5(2) . . . . ? C24 C25 C30 C29 -167.41(14) . . . . ? C25 C26 C27 C28 -0.4(3) . . . . ? C26 C25 C30 Cl2 -176.86(12) . . . . ? C26 C25 C30 C29 5.2(2) . . . . ? C26 C27 C28 O8 -175.53(15) . . . . ? C26 C27 C28 C29 4.0(2) . . . . ? C27 C28 C29 O7 176.25(15) . . . . ? C27 C28 C29 C30 -2.9(2) . . . . ? C28 C29 C30 Cl2 -179.81(12) . . . . ? C28 C29 C30 C25 -1.8(2) . . . . ? C30 C25 C26 C27 -4.1(2) . . . . ? C31 O7 C29 C28 90.9(2) . . . . ? C31 O7 C29 C30 -89.9(2) . . . . ? C32 O8 C28 C27 6.0(2) . . . . ? C32 O8 C28 C29 -173.57(15) . . . . ?