# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. # SUBMISSION DETAILS _journal_coden_Cambridge 0182 _audit_creation_date 2006-12-01 _audit_creation_method 'by CrystalStructure 3.6.0' _audit_update_record ? _publ_contact_author_name 'Manojit Pal' _publ_contact_author_address ; Discovery Research Dr. Reddy's Laboratories Miyapur, Bollaram Road Hyderabad - 500 049 ; _publ_contact_author_email manojitpal@drreddys.com _publ_contact_author_fax '91-40-2304 5438' _publ_contact_author_phone '91-40-2304 5439' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Pd-Mediated Synthesis of Substituted Benzenes Fused with Carbocycle/Heterocycle ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_address N.K.Swamy ; Discovery Research Dr. Reddy's Laboratories Miyapur, Bollaram Road Hyderabad - 500 049 ; 'Lakshmi Kumar Tatini' ; Discovery Research Dr. Reddy's Laboratories Miyapur, Bollaram Road Hyderabad - 500 049 ; 'J. Moses Babu' ; Discovery Research Dr. Reddy's Laboratories Miyapur, Bollaram Road Hyderabad - 500 049 ; 'Pazhanimuthu Annamalai' ; Discovery Research Dr. Reddy's Laboratories Miyapur, Bollaram Road Hyderabad - 500 049 ; 'Manojit Pal' ; Discovery Research Dr. Reddy's Laboratories Miyapur, Bollaram Road Hyderabad - 500 049 ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku/MSC and Rigaku Corporation. (2004). CrystalStructure 3.6.0. Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209. Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10, Chemical Crystallography Laboratory, Oxford, UK. Larson, A. C. (1970), Crystallographic Computing, 291-294. ed F. R. Ahmed, Munksgaard, Copenhagen. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_DR-587-NKS-185_CHCl3_mono _database_code_depnum_ccdc_archive 'CCDC 619549' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C23 H31 Cl3 O3 ' _chemical_formula_moiety 'C22 H30 O3, C H Cl3 ' _chemical_formula_weight 461.86 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 12.653(6) _cell_length_b 16.148(7) _cell_length_c 11.478(5) _cell_angle_alpha 90 _cell_angle_beta 93.125(6) _cell_angle_gamma 90 _cell_volume 2341.8(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9138 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976.00 _exptl_absorpt_coefficient_mu 0.412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 0.884 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 26740 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 27.40 _diffrn_measured_fraction_theta_max 0.9881 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.9881 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5278 _reflns_number_gt 2930 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.1670 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 5278 _refine_ls_number_parameters 300 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 7893.4700 10834.5000 2970.0900 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.63 _refine_diff_density_min -0.48 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 1172.1(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.5227(2) 0.9226(2) 0.7351(2) 1.000 0.0618(8) . . O2 O Uani 0.2944(2) 0.9577(2) 0.2222(2) 1.000 0.0566(8) . . O3 O Uani 0.6750(2) 0.7063(2) 0.3014(2) 1.000 0.0534(7) . . C1 C Uani 0.4538(2) 0.9284(2) 0.6553(2) 1.000 0.0492(9) . . C2 C Uani 0.4665(2) 0.8875(2) 0.5404(2) 1.000 0.0417(7) . . C3 C Uani 0.5555(2) 0.8377(2) 0.5302(2) 1.000 0.0436(7) . . C4 C Uani 0.5754(2) 0.7977(2) 0.4266(2) 1.000 0.0424(7) . . C5 C Uani 0.5039(2) 0.8126(2) 0.3320(2) 1.000 0.0450(6) . . C6 C Uani 0.4153(2) 0.8647(2) 0.3367(2) 1.000 0.0444(7) . . C7 C Uani 0.3938(2) 0.9002(2) 0.4453(2) 1.000 0.0413(7) . . C8 C Uani 0.2937(2) 0.9490(2) 0.4659(3) 1.000 0.0522(10) . . C9 C Uani 0.2638(3) 0.9473(2) 0.5920(3) 1.000 0.0646(12) . . C10 C Uani 0.3548(3) 0.9773(2) 0.6716(3) 1.000 0.0608(12) . . C11 C Uani 0.3446(2) 0.8769(2) 0.2229(3) 1.000 0.0504(12) . . C12 C Uani 0.4083(3) 0.8726(3) 0.1124(3) 1.000 0.0742(14) . . C13 C Uani 0.3352(4) 0.8800(3) 0.0002(3) 1.000 0.099(2) . . C14 C Uani 0.2506(5) 0.8143(4) -0.0035(4) 1.000 0.108(2) . . C15 C Uani 0.1861(4) 0.8197(3) 0.1028(4) 1.000 0.0856(17) . . C16 C Uani 0.2559(3) 0.8135(2) 0.2160(3) 1.000 0.0612(12) . . C17 C Uani 0.6728(2) 0.7416(2) 0.4159(2) 1.000 0.0443(6) . . C18 C Uani 0.6756(2) 0.6737(2) 0.5091(3) 1.000 0.0487(9) . . C19 C Uani 0.7775(3) 0.6242(2) 0.5166(3) 1.000 0.0603(12) . . C20 C Uani 0.8730(3) 0.6802(2) 0.5341(4) 1.000 0.0653(12) . . C21 C Uani 0.8747(2) 0.7443(2) 0.4363(3) 1.000 0.0612(14) . . C22 C Uani 0.7735(2) 0.7958(2) 0.4287(3) 1.000 0.0508(9) . . Cl1 Cl Uani 0.00094(9) 0.92424(9) 0.31974(13) 1.000 0.1012(5) . . Cl2 Cl Uani -0.04540(10) 1.04422(9) 0.14414(12) 1.000 0.1165(6) . . Cl3 Cl Uani 0.0610(2) 1.09363(10) 0.3568(2) 1.000 0.1301(6) . . C23 C Uani 0.0442(3) 1.0159(2) 0.2556(3) 1.000 0.0682(12) . . H1 H Uiso 0.60440 0.83140 0.59540 1.000 0.0520 calc R H2 H Uiso 0.51720 0.78690 0.25980 1.000 0.0540 calc R H3 H Uiso 0.23720 0.92660 0.41790 1.000 0.0620 calc R H4 H Uiso 0.30510 1.00500 0.44440 1.000 0.0620 calc R H5 H Uiso 0.24670 0.89200 0.61240 1.000 0.0770 calc R H6 H Uiso 0.20430 0.98200 0.60130 1.000 0.0770 calc R H7 H Uiso 0.33700 0.97220 0.75060 1.000 0.0730 calc R H8 H Uiso 0.36830 1.03380 0.65470 1.000 0.0730 calc R H9 H Uiso 0.44470 0.82120 0.11160 1.000 0.0890 calc R H10 H Uiso 0.45810 0.91660 0.11440 1.000 0.0890 calc R H11 H Uiso 0.37630 0.87420 -0.06620 1.000 0.1180 calc R H12 H Uiso 0.30250 0.93300 -0.00110 1.000 0.1180 calc R H13 H Uiso 0.28270 0.76120 -0.00620 1.000 0.1270 calc R H14 H Uiso 0.20500 0.82200 -0.07120 1.000 0.1270 calc R H15 H Uiso 0.13580 0.77600 0.10130 1.000 0.1010 calc R H16 H Uiso 0.15020 0.87140 0.10190 1.000 0.1010 calc R H17 H Uiso 0.28620 0.75970 0.22040 1.000 0.0720 calc R H18 H Uiso 0.21320 0.82180 0.28050 1.000 0.0720 calc R H19 H Uiso 0.61780 0.63720 0.49240 1.000 0.0580 calc R H20 H Uiso 0.66810 0.69890 0.58310 1.000 0.0580 calc R H21 H Uiso 0.78230 0.59460 0.44550 1.000 0.0720 calc R H22 H Uiso 0.77650 0.58610 0.57960 1.000 0.0720 calc R H23 H Uiso 0.93560 0.64780 0.53450 1.000 0.0780 calc R H24 H Uiso 0.86990 0.70830 0.60660 1.000 0.0780 calc R H25 H Uiso 0.87970 0.71600 0.36420 1.000 0.0730 calc R H26 H Uiso 0.93430 0.77960 0.44910 1.000 0.0730 calc R H27 H Uiso 0.77500 0.83210 0.36370 1.000 0.0610 calc R H28 H Uiso 0.77170 0.82740 0.49850 1.000 0.0610 calc R H29 H Uiso 0.335(3) 0.993(2) 0.229(3) 1.000 0.064(12) R . H30 H Uiso 0.642(4) 0.669(3) 0.306(4) 1.000 0.08(2) R . H31 H Uiso 0.11040 1.00540 0.22320 1.000 0.0820 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 0.074(2) 0.0650(10) 0.0449(11) -0.0039(10) -0.0094(10) 0.0177(12) O2 0.0569(13) 0.0528(13) 0.0586(13) 0.0033(10) -0.0091(11) 0.0116(11) O3 0.0551(13) 0.0593(13) 0.0454(11) -0.0077(10) -0.0019(9) 0.0081(11) C1 0.059(2) 0.0450(10) 0.0434(13) 0.0033(12) -0.0001(12) 0.0076(12) C2 0.0436(13) 0.0389(11) 0.0418(12) 0.0042(10) -0.0046(10) 0.0015(10) C3 0.0369(12) 0.0500(10) 0.0437(12) 0.0062(12) 0.0003(10) 0.0011(11) C4 0.0432(13) 0.0379(12) 0.0452(13) 0.0022(11) -0.0055(11) 0.0071(10) C5 0.0470(10) 0.0490(10) 0.0380(12) 0.0004(11) -0.0060(11) 0.0061(11) C6 0.0421(13) 0.0470(10) 0.0431(13) -0.0017(11) -0.0057(11) 0.0034(10) C7 0.0358(11) 0.0431(13) 0.0451(13) 0.0013(10) 0.0040(10) 0.0057(10) C8 0.0390(10) 0.061(2) 0.056(2) -0.0080(10) -0.0024(12) 0.0157(13) C9 0.055(2) 0.073(2) 0.066(2) -0.008(2) 0.006(2) 0.019(2) C10 0.068(2) 0.063(2) 0.052(2) -0.005(2) 0.0100(10) 0.018(2) C11 0.048(2) 0.054(2) 0.048(2) 0.0013(12) -0.0083(12) 0.0155(13) C12 0.079(2) 0.099(3) 0.045(2) 0.005(2) 0.006(2) 0.049(2) C13 0.117(4) 0.141(4) 0.037(2) 0.009(2) -0.004(2) 0.067(3) C14 0.133(4) 0.120(4) 0.065(2) -0.036(3) -0.049(3) 0.066(4) C15 0.087(3) 0.086(3) 0.079(3) -0.018(2) -0.038(2) 0.011(2) C16 0.062(2) 0.060(2) 0.059(2) -0.008(2) -0.019(2) 0.006(2) C17 0.0381(13) 0.0470(10) 0.0470(10) 0.0005(12) -0.0042(11) 0.0025(11) C18 0.0441(13) 0.0470(10) 0.054(2) 0.0046(13) -0.0074(12) 0.0037(11) C19 0.052(2) 0.053(2) 0.075(2) 0.010(2) -0.006(2) 0.0101(13) C20 0.048(2) 0.057(2) 0.089(2) -0.006(2) -0.013(2) 0.0110(10) C21 0.040(2) 0.048(2) 0.095(3) -0.001(2) -0.001(2) -0.0020(12) C22 0.0410(13) 0.0470(10) 0.064(2) -0.0038(13) -0.0003(12) 0.0014(11) Cl1 0.0827(8) 0.0979(9) 0.1247(11) 0.0355(8) 0.0221(7) 0.0002(6) Cl2 0.1360(13) 0.1165(11) 0.0916(9) 0.0210(8) -0.0430(8) -0.0338(9) Cl3 0.1490(10) 0.1206(12) 0.1164(11) -0.0470(10) -0.0307(10) -0.0196(10) C23 0.061(2) 0.075(2) 0.069(2) -0.003(2) 0.006(2) -0.007(2) #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C23 1.754(4) . . yes Cl2 C23 1.724(4) . . yes Cl3 C23 1.716(4) . . yes O1 C1 1.233(3) . . yes O2 C11 1.451(4) . . yes O3 C17 1.434(4) . . yes O2 H29 0.77(4) . . no O3 H30 0.74(5) . . no C1 C10 1.501(5) . . no C1 C2 1.491(4) . . no C2 C7 1.404(3) . . no C2 C3 1.394(4) . . no C3 C4 1.388(4) . . no C4 C5 1.396(3) . . no C4 C17 1.540(4) . . no C5 C6 1.405(4) . . no C6 C7 1.412(4) . . no C6 C11 1.555(4) . . no C7 C8 1.521(4) . . no C8 C9 1.516(5) . . no C9 C10 1.510(5) . . no C11 C12 1.541(5) . . no C11 C16 1.518(5) . . no C12 C13 1.549(5) . . no C13 C14 1.506(8) . . no C14 C15 1.507(7) . . no C15 C16 1.534(6) . . no C17 C18 1.531(4) . . no C17 C22 1.546(4) . . no C18 C19 1.516(5) . . no C19 C20 1.514(5) . . no C20 C21 1.528(5) . . no C21 C22 1.525(4) . . no C3 H1 0.9500 . . no C5 H2 0.9500 . . no C8 H3 0.9500 . . no C8 H4 0.9500 . . no C9 H5 0.9500 . . no C9 H6 0.9500 . . no C10 H7 0.9500 . . no C10 H8 0.9500 . . no C12 H10 0.9500 . . no C12 H9 0.9500 . . no C13 H11 0.9500 . . no C13 H12 0.9500 . . no C14 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H16 0.9500 . . no C15 H15 0.9500 . . no C16 H18 0.9500 . . no C16 H17 0.9500 . . no C18 H19 0.9500 . . no C18 H20 0.9500 . . no C19 H21 0.9500 . . no C19 H22 0.9500 . . no C20 H24 0.9500 . . no C20 H23 0.9500 . . no C21 H25 0.9500 . . no C21 H26 0.9500 . . no C22 H27 0.9500 . . no C22 H28 0.9500 . . no C23 H31 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O2 H29 112(3) . . . no C17 O3 H30 103(4) . . . no O1 C1 C2 121.2(3) . . . yes O1 C1 C10 120.6(3) . . . yes C2 C1 C10 118.3(2) . . . no C1 C2 C3 117.1(2) . . . no C3 C2 C7 121.1(2) . . . no C1 C2 C7 121.7(2) . . . no C2 C3 C4 121.7(2) . . . no C3 C4 C5 116.5(3) . . . no C3 C4 C17 121.7(2) . . . no C5 C4 C17 121.8(2) . . . no C4 C5 C6 123.9(2) . . . no C7 C6 C11 124.1(2) . . . no C5 C6 C11 117.9(2) . . . no C5 C6 C7 118.0(2) . . . no C2 C7 C8 118.1(2) . . . no C6 C7 C8 123.4(2) . . . no C2 C7 C6 118.5(2) . . . no C7 C8 C9 113.1(3) . . . no C8 C9 C10 110.5(3) . . . no C1 C10 C9 111.7(3) . . . no O2 C11 C16 106.5(2) . . . yes C6 C11 C12 112.5(2) . . . no C6 C11 C16 110.4(3) . . . no C12 C11 C16 110.2(3) . . . no O2 C11 C6 110.5(3) . . . yes O2 C11 C12 106.5(3) . . . yes C11 C12 C13 111.4(3) . . . no C12 C13 C14 111.1(4) . . . no C13 C14 C15 110.6(4) . . . no C14 C15 C16 111.7(4) . . . no C11 C16 C15 113.0(3) . . . no O3 C17 C4 111.3(2) . . . yes C4 C17 C18 110.7(2) . . . no O3 C17 C18 110.8(3) . . . yes O3 C17 C22 104.8(2) . . . yes C18 C17 C22 110.6(2) . . . no C4 C17 C22 108.6(2) . . . no C17 C18 C19 113.9(2) . . . no C18 C19 C20 111.3(3) . . . no C19 C20 C21 110.5(3) . . . no C20 C21 C22 111.5(3) . . . no C17 C22 C21 112.4(3) . . . no C2 C3 H1 119.00 . . . no C4 C3 H1 119.00 . . . no C4 C5 H2 118.00 . . . no C6 C5 H2 118.00 . . . no C7 C8 H3 109.00 . . . no C7 C8 H4 108.00 . . . no C9 C8 H3 109.00 . . . no C9 C8 H4 108.00 . . . no H3 C8 H4 109.00 . . . no C8 C9 H5 109.00 . . . no C8 C9 H6 110.00 . . . no C10 C9 H5 109.00 . . . no C10 C9 H6 109.00 . . . no H5 C9 H6 110.00 . . . no C1 C10 H7 108.00 . . . no C1 C10 H8 109.00 . . . no C9 C10 H7 110.00 . . . no C9 C10 H8 109.00 . . . no H7 C10 H8 109.00 . . . no C11 C12 H9 109.00 . . . no C11 C12 H10 109.00 . . . no C13 C12 H9 109.00 . . . no C13 C12 H10 109.00 . . . no H9 C12 H10 109.00 . . . no C12 C13 H11 109.00 . . . no C12 C13 H12 109.00 . . . no C14 C13 H11 109.00 . . . no C14 C13 H12 109.00 . . . no H11 C13 H12 109.00 . . . no C13 C14 H13 109.00 . . . no C13 C14 H14 109.00 . . . no C15 C14 H13 109.00 . . . no C15 C14 H14 109.00 . . . no H13 C14 H14 109.00 . . . no C14 C15 H15 110.00 . . . no C14 C15 H16 109.00 . . . no C16 C15 H15 109.00 . . . no C16 C15 H16 109.00 . . . no H15 C15 H16 109.00 . . . no C11 C16 H17 109.00 . . . no C11 C16 H18 108.00 . . . no C15 C16 H17 108.00 . . . no C15 C16 H18 109.00 . . . no H17 C16 H18 109.00 . . . no C17 C18 H19 108.00 . . . no C17 C18 H20 109.00 . . . no C19 C18 H19 109.00 . . . no C19 C18 H20 108.00 . . . no H19 C18 H20 109.00 . . . no C18 C19 H21 108.00 . . . no C18 C19 H22 110.00 . . . no C20 C19 H21 109.00 . . . no C20 C19 H22 109.00 . . . no H21 C19 H22 109.00 . . . no C19 C20 H23 109.00 . . . no C19 C20 H24 109.00 . . . no C21 C20 H23 109.00 . . . no C21 C20 H24 109.00 . . . no H23 C20 H24 109.00 . . . no C20 C21 H25 109.00 . . . no C20 C21 H26 110.00 . . . no C22 C21 H25 108.00 . . . no C22 C21 H26 110.00 . . . no H25 C21 H26 109.00 . . . no C17 C22 H27 109.00 . . . no C17 C22 H28 109.00 . . . no C21 C22 H27 109.00 . . . no C21 C22 H28 108.00 . . . no H27 C22 H28 109.00 . . . no Cl1 C23 Cl2 109.1(2) . . . yes Cl1 C23 Cl3 111.3(2) . . . yes Cl2 C23 Cl3 111.1(2) . . . yes Cl1 C23 H31 108.00 . . . no Cl2 C23 H31 108.00 . . . no Cl3 C23 H31 108.00 . . . no 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 O1 C1 C2 C3 4.6(4) . . . . no O1 C1 C2 C7 -173.7(3) . . . . no C10 C1 C2 C3 -175.6(3) . . . . no C10 C1 C2 C7 6.2(4) . . . . no O1 C1 C10 C9 -154.5(3) . . . . no C2 C1 C10 C9 25.7(4) . . . . no C1 C2 C3 C4 -179.2(3) . . . . no C7 C2 C3 C4 -0.9(5) . . . . no C1 C2 C7 C6 175.1(3) . . . . no C1 C2 C7 C8 -7.1(4) . . . . no C3 C2 C7 C6 -3.1(4) . . . . no C3 C2 C7 C8 174.7(3) . . . . no C2 C3 C4 C5 2.5(4) . . . . no C2 C3 C4 C17 -179.0(3) . . . . no C3 C4 C5 C6 0.0(4) . . . . no C17 C4 C5 C6 -178.5(3) . . . . no C3 C4 C17 O3 179.0(3) . . . . no C3 C4 C17 C18 55.3(4) . . . . no C3 C4 C17 C22 -66.2(3) . . . . no C5 C4 C17 O3 -2.6(4) . . . . no C5 C4 C17 C18 -126.2(3) . . . . no C5 C4 C17 C22 112.2(3) . . . . no C4 C5 C6 C7 -3.9(5) . . . . no C4 C5 C6 C11 178.4(3) . . . . no C5 C6 C7 C2 5.3(4) . . . . no C5 C6 C7 C8 -172.3(3) . . . . no C11 C6 C7 C2 -177.1(3) . . . . no C11 C6 C7 C8 5.2(5) . . . . no C5 C6 C11 O2 -151.0(3) . . . . no C5 C6 C11 C12 -32.1(4) . . . . no C5 C6 C11 C16 91.4(3) . . . . no C7 C6 C11 O2 31.4(4) . . . . no C7 C6 C11 C12 150.4(3) . . . . no C7 C6 C11 C16 -86.1(4) . . . . no C2 C7 C8 C9 -23.8(4) . . . . no C6 C7 C8 C9 153.9(3) . . . . no C7 C8 C9 C10 55.3(3) . . . . no C8 C9 C10 C1 -55.6(3) . . . . no O2 C11 C12 C13 -62.0(4) . . . . no C6 C11 C12 C13 176.8(3) . . . . no C16 C11 C12 C13 53.2(4) . . . . no O2 C11 C16 C15 62.6(4) . . . . no C6 C11 C16 C15 -177.4(3) . . . . no C12 C11 C16 C15 -52.5(4) . . . . no C11 C12 C13 C14 -56.5(5) . . . . no C12 C13 C14 C15 57.4(6) . . . . no C13 C14 C15 C16 -56.2(6) . . . . no C14 C15 C16 C11 54.7(5) . . . . no O3 C17 C18 C19 65.1(3) . . . . no C4 C17 C18 C19 -171.0(3) . . . . no C22 C17 C18 C19 -50.6(3) . . . . no O3 C17 C22 C21 -69.0(3) . . . . no C4 C17 C22 C21 172.0(2) . . . . no C18 C17 C22 C21 50.4(3) . . . . no C17 C18 C19 C20 54.6(4) . . . . no C18 C19 C20 C21 -56.6(4) . . . . no C19 C20 C21 C22 57.2(4) . . . . no C20 C21 C22 C17 -54.6(4) . . . . no 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 # #D H A D - H H...A D...A D - H...A symm(A) # O2 H29 O1 0.77(4) 2.28(4) 3.035(4) 168(3) 3_676 yes O3 H30 O1 0.74(5) 2.24(5) 2.910(4) 153(5) 4_564 yes C3 H1 O1 0.9500 2.4500 2.773(4) 100.00 . yes C3 H1 O3 0.9500 2.5600 3.459(4) 159.00 4_565 yes C5 H2 O3 0.9500 2.4100 2.800(4) 104.00 . yes C8 H3 O2 0.9500 2.4500 2.801(4) 102.00 . yes C23 H31 O2 0.9500 2.4500 3.344(5) 156.00 . yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END