# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_General _journal_name_full 'New J.Chem.' #TrackingRef '- TolueneDDQadductCIF_revised.cif' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _audit_creation_date 2010-10-13 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Dr. Robert H Crabtree' _publ_contact_author_email robert.crabtree@yale.edu _publ_contact_author_fax '+203 432 6144' _publ_contact_author_phone '+203 432 3925' _publ_requested_category QO _publ_contact_author_address ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Oxidative Functionalization of Benzylic C-H Bonds by DDQ ; loop_ _publ_author_name _publ_author_address V.S.Batista ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; R.H.Crabtree ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; S.J.Konezny ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; O.R.Luca ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; J.M.Praetorius ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku Americas and Rigaku Corporation. (2010). CrystalStructure (Version 4.0). Single Crystal Structure Analysis Software. Rigaku Americas, 9009 TX, USA 77381-5209. Rigaku, Tokyo 196-8666, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. ; _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_BenzylDDQ _database_code_depnum_ccdc_archive 'CCDC 864075' #TrackingRef '- TolueneDDQadductCIF_revised.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H8 Cl2 N2 O2' _chemical_formula_moiety 'C15 H8 Cl2 N2 O2' _chemical_formula_weight 319.15 _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 12.036(5) _cell_length_b 23.769(9) _cell_length_c 10.114(4) _cell_angle_alpha 90.0000 _cell_angle_beta 99.954(6) _cell_angle_gamma 90.0000 _cell_volume 2850.1(18) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5937 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 25.18 _cell_measurement_temperature 223 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296.00 _exptl_absorpt_coefficient_mu 0.459 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.955 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 223 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury275R CCD (SCX mini)' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.849 _diffrn_reflns_number 15658 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed 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). The positions of phenolic H atoms H1 and H3 were determined using a rotating group refinement. ; _reflns_number_total 5016 _reflns_number_gt 3402 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1481 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5007 _refine_ls_number_parameters 381 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.8456P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.260 _refine_diff_density_min -0.400 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 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) ; N N 0.006 0.003 ; 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 THERMAL PARAMETERS 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl 0.60146(9) -0.02921(4) 0.66364(12) 0.0831(4) Uani 1.00 4 d . . . Cl(2) Cl 0.72036(10) 0.05807(4) 0.50650(12) 0.0821(4) Uani 1.00 4 d . . . Cl(3) Cl 0.87585(8) 0.22498(4) -0.19684(9) 0.0638(3) Uani 1.00 4 d . . . Cl(4) Cl 0.75687(9) 0.31275(3) -0.04265(10) 0.0698(3) Uani 1.00 4 d . . . O(1) O 0.68703(19) -0.14570(8) 0.6474(2) 0.0531(6) Uani 1.00 4 d . . . O(2) O 0.90921(18) 0.01071(9) 0.3903(2) 0.0498(5) Uani 1.00 4 d . . . O(3) O 0.8020(2) 0.10694(9) -0.1616(2) 0.0603(6) Uani 1.00 4 d . . . O(4) O 0.60379(18) 0.26255(9) 0.1256(2) 0.0511(6) Uani 1.00 4 d . . . N(1) N 0.8717(3) -0.22799(13) 0.5159(4) 0.0816(10) Uani 1.00 4 d . . . N(2) N 1.0313(3) -0.11203(14) 0.3183(4) 0.0805(10) Uani 1.00 4 d . . . N(3) N 0.6422(3) 0.02378(12) 0.0055(3) 0.0664(8) Uani 1.00 4 d . . . N(4) N 0.4856(3) 0.14063(13) 0.2036(3) 0.0752(9) Uani 1.00 4 d . . . C(1) C 0.7367(3) -0.10655(12) 0.5848(3) 0.0422(7) Uani 1.00 4 d . . . C(2) C 0.7070(3) -0.04962(13) 0.5815(3) 0.0473(8) Uani 1.00 4 d . . . C(3) C 0.7605(3) -0.01125(12) 0.5126(3) 0.0470(8) Uani 1.00 4 d . . . C(4) C 0.8485(3) -0.02722(12) 0.4479(3) 0.0425(7) Uani 1.00 4 d . . . C(5) C 0.8768(3) -0.08352(13) 0.4494(3) 0.0433(7) Uani 1.00 4 d . . . C(6) C 0.8220(3) -0.12323(12) 0.5175(3) 0.0417(7) Uani 1.00 4 d . . . C(7) C 0.8506(3) -0.18189(15) 0.5177(3) 0.0531(8) Uani 1.00 4 d . . . C(8) C 0.9640(3) -0.10024(14) 0.3782(3) 0.0542(8) Uani 1.00 4 d . . . C(9) C 0.8651(4) 0.02351(19) 0.2524(4) 0.0801(13) Uani 1.00 4 d . . . C(10) C 0.9491(3) 0.05998(15) 0.1993(3) 0.0563(9) Uani 1.00 4 d . . . C(11) C 1.0387(4) 0.03597(16) 0.1522(4) 0.0680(10) Uani 1.00 4 d . . . C(12) C 1.1147(4) 0.06911(18) 0.1003(4) 0.0758(11) Uani 1.00 4 d . . . C(13) C 1.1003(4) 0.12686(17) 0.0954(4) 0.0703(11) Uani 1.00 4 d . . . C(14) C 1.0139(4) 0.15035(16) 0.1439(4) 0.0683(10) Uani 1.00 4 d . . . C(15) C 0.9390(3) 0.11749(16) 0.1966(4) 0.0657(10) Uani 1.00 4 d . . . C(16) C 0.7546(3) 0.14655(13) -0.0972(3) 0.0429(7) Uani 1.00 4 d . . . C(17) C 0.7780(3) 0.20399(13) -0.1038(3) 0.0439(7) Uani 1.00 4 d . . . C(18) C 0.7259(3) 0.24262(12) -0.0337(3) 0.0449(7) Uani 1.00 4 d . . . C(19) C 0.6496(3) 0.22569(12) 0.0473(3) 0.0438(7) Uani 1.00 4 d . . . C(20) C 0.6262(3) 0.16892(13) 0.0541(3) 0.0429(7) Uani 1.00 4 d . . . C(21) C 0.6785(3) 0.12945(12) -0.0173(3) 0.0411(7) Uani 1.00 4 d . . . C(22) C 0.6578(3) 0.06981(15) -0.0063(3) 0.0499(8) Uani 1.00 4 d . . . C(23) C 0.5481(3) 0.15163(14) 0.1382(3) 0.0524(8) Uani 1.00 4 d . . . C(24) C 0.5013(3) 0.28957(17) 0.0581(3) 0.0715(11) Uani 1.00 4 d . . . C(25) C 0.4501(3) 0.32101(14) 0.1601(3) 0.0504(8) Uani 1.00 4 d . . . C(26) C 0.3765(3) 0.29492(15) 0.2296(4) 0.0626(10) Uani 1.00 4 d . . . C(27) C 0.3255(3) 0.32407(18) 0.3202(4) 0.0734(11) Uani 1.00 4 d . . . C(28) C 0.3487(4) 0.38044(18) 0.3411(4) 0.0705(11) Uani 1.00 4 d . . . C(29) C 0.4212(3) 0.40657(15) 0.2735(4) 0.0662(10) Uani 1.00 4 d . . . C(30) C 0.4717(3) 0.37766(15) 0.1832(4) 0.0598(9) Uani 1.00 4 d . . . H(1) H 0.6415 -0.1306 0.6894 0.064 Uiso 1.00 4 calc R . . H(3) H 0.8555 0.1207 -0.1926 0.072 Uiso 1.00 4 calc R . . H(9A) H 0.7929 0.0432 0.2456 0.096 Uiso 1.00 4 calc R . . H(9B) H 0.8527 -0.0113 0.1999 0.096 Uiso 1.00 4 calc R . . H(11) H 1.0481 -0.0033 0.1555 0.082 Uiso 1.00 4 calc R . . H(12) H 1.1759 0.0526 0.0683 0.091 Uiso 1.00 4 calc R . . H(13) H 1.1509 0.1497 0.0584 0.084 Uiso 1.00 4 calc R . . H(14) H 1.0050 0.1896 0.1415 0.082 Uiso 1.00 4 calc R . . H(15) H 0.8797 0.1346 0.2314 0.079 Uiso 1.00 4 calc R . . H(24A) H 0.4483 0.2612 0.0144 0.086 Uiso 1.00 4 calc R . . H(24B) H 0.5189 0.3155 -0.0107 0.086 Uiso 1.00 4 calc R . . H(26) H 0.3605 0.2565 0.2151 0.075 Uiso 1.00 4 calc R . . H(27) H 0.2753 0.3057 0.3674 0.088 Uiso 1.00 4 calc R . . H(28) H 0.3141 0.4007 0.4026 0.085 Uiso 1.00 4 calc R . . H(29) H 0.4370 0.4450 0.2886 0.079 Uiso 1.00 4 calc R . . H(30) H 0.5215 0.3965 0.1363 0.072 Uiso 1.00 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0912(8) 0.0616(6) 0.1167(9) 0.0060(6) 0.0744(7) -0.0046(5) Cl(2) 0.0935(8) 0.0387(5) 0.1262(9) 0.0042(5) 0.0526(7) 0.0034(5) Cl(3) 0.0666(6) 0.0665(6) 0.0677(6) -0.0125(5) 0.0383(5) 0.0018(4) Cl(4) 0.0972(8) 0.0408(5) 0.0781(6) -0.0083(5) 0.0342(5) 0.0005(4) O(1) 0.0593(14) 0.0468(13) 0.0610(14) -0.0086(12) 0.0326(11) 0.0030(10) O(2) 0.0506(12) 0.0559(13) 0.0436(12) -0.0145(11) 0.0099(10) 0.0103(10) O(3) 0.0680(16) 0.0502(13) 0.0746(16) -0.0034(12) 0.0452(13) -0.0108(11) O(4) 0.0591(14) 0.0519(13) 0.0444(12) 0.0140(12) 0.0147(10) -0.0055(10) N(1) 0.088(3) 0.0510(20) 0.107(3) 0.0154(19) 0.020(2) -0.0013(18) N(2) 0.075(2) 0.082(2) 0.100(3) 0.0046(19) 0.058(2) -0.0055(19) N(3) 0.074(2) 0.0458(18) 0.080(2) -0.0073(17) 0.0160(17) 0.0065(15) N(4) 0.086(2) 0.077(2) 0.076(2) -0.0083(19) 0.0529(19) 0.0059(17) C(1) 0.0417(17) 0.0438(18) 0.0446(17) -0.0059(15) 0.0169(14) -0.0008(13) C(2) 0.0482(18) 0.0458(18) 0.0534(18) -0.0005(16) 0.0244(15) -0.0061(14) C(3) 0.0507(19) 0.0357(17) 0.0571(19) -0.0041(16) 0.0163(16) -0.0011(14) C(4) 0.0426(17) 0.0418(18) 0.0442(17) -0.0070(15) 0.0109(14) 0.0002(13) C(5) 0.0398(17) 0.0516(19) 0.0413(16) -0.0030(16) 0.0148(13) -0.0027(14) C(6) 0.0419(17) 0.0396(17) 0.0448(17) -0.0011(15) 0.0112(14) -0.0024(13) C(7) 0.050(2) 0.048(2) 0.065(2) 0.0023(18) 0.0192(16) -0.0024(16) C(8) 0.0514(20) 0.052(2) 0.064(2) 0.0002(17) 0.0251(18) 0.0010(16) C(9) 0.076(3) 0.103(3) 0.055(2) -0.031(2) -0.0028(19) 0.024(2) C(10) 0.065(2) 0.066(2) 0.0378(17) -0.016(2) 0.0080(16) 0.0113(15) C(11) 0.097(3) 0.052(2) 0.057(2) -0.010(2) 0.019(2) 0.0023(17) C(12) 0.088(3) 0.083(3) 0.064(2) 0.000(3) 0.033(2) -0.005(2) C(13) 0.081(3) 0.075(3) 0.058(2) -0.024(2) 0.022(2) 0.0107(19) C(14) 0.088(3) 0.052(2) 0.065(2) -0.005(2) 0.015(2) 0.0098(18) C(15) 0.070(2) 0.073(3) 0.056(2) -0.000(2) 0.0151(19) 0.0092(18) C(16) 0.0421(17) 0.0477(18) 0.0425(16) 0.0018(16) 0.0175(14) -0.0047(13) C(17) 0.0441(17) 0.0461(18) 0.0447(17) -0.0071(15) 0.0166(14) 0.0031(14) C(18) 0.0543(19) 0.0409(17) 0.0418(17) 0.0014(16) 0.0143(15) 0.0015(13) C(19) 0.0472(18) 0.0436(18) 0.0431(17) 0.0062(16) 0.0149(14) -0.0016(13) C(20) 0.0422(17) 0.0494(19) 0.0406(16) 0.0006(15) 0.0166(13) 0.0010(13) C(21) 0.0457(17) 0.0360(16) 0.0444(17) 0.0005(15) 0.0159(14) 0.0023(13) C(22) 0.0497(20) 0.055(2) 0.0481(18) -0.0010(18) 0.0168(15) 0.0007(15) C(23) 0.059(2) 0.0533(20) 0.0512(19) 0.0008(18) 0.0260(17) -0.0029(15) C(24) 0.076(3) 0.086(3) 0.052(2) 0.035(2) 0.0099(19) -0.0054(19) C(25) 0.0525(20) 0.057(2) 0.0426(17) 0.0142(18) 0.0110(15) 0.0007(15) C(26) 0.070(2) 0.047(2) 0.072(2) 0.0079(19) 0.014(2) 0.0048(17) C(27) 0.069(3) 0.089(3) 0.072(3) 0.013(2) 0.038(2) 0.020(2) C(28) 0.073(3) 0.080(3) 0.061(2) 0.030(2) 0.019(2) -0.009(2) C(29) 0.071(2) 0.050(2) 0.074(3) 0.010(2) 0.004(2) -0.0134(18) C(30) 0.055(2) 0.062(2) 0.064(2) 0.0008(19) 0.0134(17) 0.0038(18) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl(1) C(2) 1.704(4) yes . . Cl(2) C(3) 1.715(3) yes . . Cl(3) C(17) 1.704(3) yes . . Cl(4) C(18) 1.714(3) yes . . O(1) C(1) 1.325(4) yes . . O(2) C(4) 1.354(4) yes . . O(2) C(9) 1.437(4) yes . . O(3) C(16) 1.328(4) yes . . O(4) C(19) 1.361(4) yes . . O(4) C(24) 1.452(4) yes . . N(1) C(7) 1.126(5) yes . . N(2) C(8) 1.127(5) yes . . N(3) C(22) 1.120(5) yes . . N(4) C(23) 1.116(5) yes . . C(1) C(2) 1.399(4) yes . . C(1) C(6) 1.385(4) yes . . C(2) C(3) 1.374(5) yes . . C(3) C(4) 1.390(5) yes . . C(4) C(5) 1.380(4) yes . . C(5) C(6) 1.398(4) yes . . C(5) C(8) 1.428(5) yes . . C(6) C(7) 1.436(5) yes . . C(9) C(10) 1.500(6) yes . . C(10) C(11) 1.375(6) yes . . C(10) C(15) 1.372(5) yes . . C(11) C(12) 1.378(6) yes . . C(12) C(13) 1.383(6) yes . . C(13) C(14) 1.345(6) yes . . C(14) C(15) 1.369(6) yes . . C(16) C(17) 1.398(4) yes . . C(16) C(21) 1.383(4) yes . . C(17) C(18) 1.376(4) yes . . C(18) C(19) 1.392(5) yes . . C(19) C(20) 1.383(4) yes . . C(20) C(21) 1.398(4) yes . . C(20) C(23) 1.432(5) yes . . C(21) C(22) 1.447(5) yes . . C(24) C(25) 1.491(5) yes . . C(25) C(26) 1.371(5) yes . . C(25) C(30) 1.383(5) yes . . C(26) C(27) 1.375(6) yes . . C(27) C(28) 1.378(6) yes . . C(28) C(29) 1.349(6) yes . . C(29) C(30) 1.366(6) yes . . O(1) H(1) 0.830 yes . . O(3) H(3) 0.830 yes . . C(9) H(9A) 0.980 yes . . C(9) H(9B) 0.980 yes . . C(11) H(11) 0.940 yes . . C(12) H(12) 0.940 yes . . C(13) H(13) 0.940 yes . . C(14) H(14) 0.940 yes . . C(15) H(15) 0.940 yes . . C(24) H(24A) 0.980 yes . . C(24) H(24B) 0.980 yes . . C(26) H(26) 0.940 yes . . C(27) H(27) 0.940 yes . . C(28) H(28) 0.940 yes . . C(29) H(29) 0.940 yes . . C(30) H(30) 0.940 yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(4) O(2) C(9) 115.0(2) yes . . . C(19) O(4) C(24) 114.1(2) yes . . . O(1) C(1) C(2) 123.8(3) yes . . . O(1) C(1) C(6) 117.9(3) yes . . . C(2) C(1) C(6) 118.3(3) yes . . . Cl(1) C(2) C(1) 118.2(3) yes . . . Cl(1) C(2) C(3) 120.8(2) yes . . . C(1) C(2) C(3) 120.9(3) yes . . . Cl(2) C(3) C(2) 120.1(3) yes . . . Cl(2) C(3) C(4) 118.6(2) yes . . . C(2) C(3) C(4) 121.3(3) yes . . . O(2) C(4) C(3) 122.2(3) yes . . . O(2) C(4) C(5) 120.0(3) yes . . . C(3) C(4) C(5) 117.8(3) yes . . . C(4) C(5) C(6) 121.6(3) yes . . . C(4) C(5) C(8) 117.7(3) yes . . . C(6) C(5) C(8) 120.7(3) yes . . . C(1) C(6) C(5) 120.1(3) yes . . . C(1) C(6) C(7) 118.3(3) yes . . . C(5) C(6) C(7) 121.6(3) yes . . . N(1) C(7) C(6) 178.8(3) yes . . . N(2) C(8) C(5) 177.4(4) yes . . . O(2) C(9) C(10) 108.1(3) yes . . . C(9) C(10) C(11) 120.1(3) yes . . . C(9) C(10) C(15) 121.3(4) yes . . . C(11) C(10) C(15) 118.6(4) yes . . . C(10) C(11) C(12) 120.4(4) yes . . . C(11) C(12) C(13) 119.6(4) yes . . . C(12) C(13) C(14) 119.9(4) yes . . . C(13) C(14) C(15) 120.5(4) yes . . . C(10) C(15) C(14) 120.9(4) yes . . . O(3) C(16) C(17) 124.2(3) yes . . . O(3) C(16) C(21) 117.5(3) yes . . . C(17) C(16) C(21) 118.3(3) yes . . . Cl(3) C(17) C(16) 118.5(2) yes . . . Cl(3) C(17) C(18) 120.6(2) yes . . . C(16) C(17) C(18) 120.9(3) yes . . . Cl(4) C(18) C(17) 120.0(3) yes . . . Cl(4) C(18) C(19) 118.9(2) yes . . . C(17) C(18) C(19) 121.1(3) yes . . . O(4) C(19) C(18) 122.1(3) yes . . . O(4) C(19) C(20) 119.5(3) yes . . . C(18) C(19) C(20) 118.2(3) yes . . . C(19) C(20) C(21) 121.0(3) yes . . . C(19) C(20) C(23) 118.0(3) yes . . . C(21) C(20) C(23) 121.0(3) yes . . . C(16) C(21) C(20) 120.5(3) yes . . . C(16) C(21) C(22) 118.3(3) yes . . . C(20) C(21) C(22) 121.2(3) yes . . . N(3) C(22) C(21) 178.4(3) yes . . . N(4) C(23) C(20) 176.8(4) yes . . . O(4) C(24) C(25) 108.4(3) yes . . . C(24) C(25) C(26) 120.6(3) yes . . . C(24) C(25) C(30) 121.1(3) yes . . . C(26) C(25) C(30) 118.2(3) yes . . . C(25) C(26) C(27) 121.1(3) yes . . . C(26) C(27) C(28) 119.4(4) yes . . . C(27) C(28) C(29) 120.1(4) yes . . . C(28) C(29) C(30) 120.6(4) yes . . . C(25) C(30) C(29) 120.7(3) yes . . . C(1) O(1) H(1) 109.482 yes . . . C(16) O(3) H(3) 109.482 yes . . . O(2) C(9) H(9A) 110.084 yes . . . O(2) C(9) H(9B) 110.078 yes . . . C(10) C(9) H(9A) 110.078 yes . . . C(10) C(9) H(9B) 110.074 yes . . . H(9A) C(9) H(9B) 108.411 yes . . . C(10) C(11) H(11) 119.799 yes . . . C(12) C(11) H(11) 119.778 yes . . . C(11) C(12) H(12) 120.234 yes . . . C(13) C(12) H(12) 120.209 yes . . . C(12) C(13) H(13) 120.031 yes . . . C(14) C(13) H(13) 120.029 yes . . . C(13) C(14) H(14) 119.735 yes . . . C(15) C(14) H(14) 119.739 yes . . . C(10) C(15) H(15) 119.557 yes . . . C(14) C(15) H(15) 119.546 yes . . . O(4) C(24) H(24A) 110.007 yes . . . O(4) C(24) H(24B) 110.019 yes . . . C(25) C(24) H(24A) 110.019 yes . . . C(25) C(24) H(24B) 110.027 yes . . . H(24A) C(24) H(24B) 108.385 yes . . . C(25) C(26) H(26) 119.469 yes . . . C(27) C(26) H(26) 119.454 yes . . . C(26) C(27) H(27) 120.310 yes . . . C(28) C(27) H(27) 120.315 yes . . . C(27) C(28) H(28) 119.944 yes . . . C(29) C(28) H(28) 119.944 yes . . . C(28) C(29) H(29) 119.719 yes . . . C(30) C(29) H(29) 119.728 yes . . . C(25) C(30) H(30) 119.640 yes . . . C(29) C(30) H(30) 119.666 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(9) O(2) C(4) C(3) -89.4(3) no . . . . C(9) O(2) C(4) C(5) 94.0(3) no . . . . C(24) O(4) C(19) C(18) 87.9(3) no . . . . C(24) O(4) C(19) C(20) -96.5(3) no . . . . O(1) C(1) C(2) Cl(1) 0.4(4) no . . . . O(1) C(1) C(6) C(7) 0.9(4) no . . . . C(2) C(1) C(6) C(5) 0.5(4) no . . . . C(6) C(1) C(2) C(3) 0.4(4) no . . . . Cl(1) C(2) C(3) Cl(2) -0.8(4) no . . . . C(1) C(2) C(3) C(4) -2.3(4) no . . . . Cl(2) C(3) C(4) O(2) 5.7(4) no . . . . C(2) C(3) C(4) C(5) 3.1(4) no . . . . O(2) C(4) C(5) C(8) -5.7(4) no . . . . C(3) C(4) C(5) C(6) -2.2(4) no . . . . C(4) C(5) C(6) C(1) 0.4(4) no . . . . C(8) C(5) C(6) C(7) -0.4(4) no . . . . O(2) C(9) C(10) C(11) 83.9(4) no . . . . O(2) C(9) C(10) C(15) -96.1(3) no . . . . C(11) C(10) C(15) C(14) 2.2(5) no . . . . C(15) C(10) C(11) C(12) -1.7(5) no . . . . C(10) C(11) C(12) C(13) -0.1(5) no . . . . C(11) C(12) C(13) C(14) 1.4(5) no . . . . C(12) C(13) C(14) C(15) -0.8(5) no . . . . C(13) C(14) C(15) C(10) -1.0(5) no . . . . O(3) C(16) C(17) Cl(3) -1.6(4) no . . . . O(3) C(16) C(21) C(22) 1.6(4) no . . . . C(17) C(16) C(21) C(20) 0.4(4) no . . . . C(21) C(16) C(17) C(18) -0.7(4) no . . . . Cl(3) C(17) C(18) Cl(4) 1.5(3) no . . . . C(16) C(17) C(18) C(19) 0.9(4) no . . . . Cl(4) C(18) C(19) O(4) -3.9(4) no . . . . C(17) C(18) C(19) C(20) -0.9(4) no . . . . O(4) C(19) C(20) C(23) 3.9(4) no . . . . C(18) C(19) C(20) C(21) 0.6(4) no . . . . C(19) C(20) C(21) C(16) -0.3(4) no . . . . C(23) C(20) C(21) C(22) -1.6(4) no . . . . O(4) C(24) C(25) C(26) -87.9(3) no . . . . O(4) C(24) C(25) C(30) 94.9(3) no . . . . C(26) C(25) C(30) C(29) 0.4(4) no . . . . C(30) C(25) C(26) C(27) -0.2(5) no . . . . C(25) C(26) C(27) C(28) 0.2(5) no . . . . C(26) C(27) C(28) C(29) -0.2(5) no . . . . C(27) C(28) C(29) C(30) 0.4(5) no . . . . C(28) C(29) C(30) C(25) -0.4(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cl(1) Cl(2) 3.1088(18) yes . . Cl(1) O(1) 2.969(2) yes . . Cl(2) O(2) 2.956(3) yes . . Cl(2) C(9) 3.445(4) yes . . Cl(3) Cl(4) 3.0996(15) yes . . Cl(3) O(3) 2.983(3) yes . . Cl(4) O(4) 2.967(3) yes . . Cl(4) C(24) 3.448(4) yes . . O(1) N(1) 3.400(4) yes . . O(1) C(7) 2.689(4) yes . . O(2) N(2) 3.401(4) yes . . O(2) C(8) 2.726(4) yes . . O(2) C(11) 3.144(5) yes . . O(2) C(15) 3.264(4) yes . . O(3) N(3) 3.404(4) yes . . O(3) C(22) 2.684(4) yes . . O(4) N(4) 3.381(4) yes . . O(4) C(23) 2.729(4) yes . . O(4) C(26) 3.191(5) yes . . O(4) C(30) 3.267(4) yes . . N(1) C(1) 3.443(5) yes . . N(1) C(5) 3.502(5) yes . . N(1) C(8) 3.595(5) yes . . N(2) C(4) 3.409(5) yes . . N(2) C(6) 3.496(5) yes . . N(3) C(16) 3.451(4) yes . . N(3) C(20) 3.495(4) yes . . N(3) C(23) 3.584(5) yes . . N(4) C(19) 3.401(5) yes . . N(4) C(21) 3.500(5) yes . . C(1) C(4) 2.816(4) yes . . C(2) C(5) 2.748(5) yes . . C(3) C(6) 2.761(4) yes . . C(3) C(9) 3.215(5) yes . . C(5) C(9) 3.220(5) yes . . C(7) C(8) 2.879(5) yes . . C(8) C(9) 3.341(6) yes . . C(10) C(13) 2.757(6) yes . . C(11) C(14) 2.735(5) yes . . C(12) C(15) 2.731(6) yes . . C(16) C(19) 2.813(4) yes . . C(17) C(20) 2.756(5) yes . . C(18) C(21) 2.761(4) yes . . C(18) C(24) 3.207(5) yes . . C(20) C(24) 3.241(5) yes . . C(22) C(23) 2.885(5) yes . . C(23) C(24) 3.401(5) yes . . C(25) C(28) 2.758(5) yes . . C(26) C(29) 2.729(5) yes . . C(27) C(30) 2.735(6) yes . . Cl(1) N(4) 3.225(4) yes . 3_656 Cl(2) Cl(4) 3.1534(16) yes . 4_555 Cl(2) O(3) 3.527(3) yes . 1_556 Cl(2) N(2) 3.448(4) yes . 3_756 Cl(3) O(4) 3.464(2) yes . 4_554 Cl(3) N(1) 3.451(4) yes . 2_755 Cl(3) N(2) 3.231(4) yes . 3_755 Cl(4) Cl(2) 3.1534(16) yes . 4_554 Cl(4) N(2) 3.585(3) yes . 2_755 O(1) N(4) 2.772(4) yes . 3_656 O(1) C(13) 3.349(4) yes . 3_756 O(1) C(24) 3.194(4) yes . 2_645 O(1) C(25) 3.355(4) yes . 2_645 O(1) C(30) 3.596(4) yes . 2_645 O(2) O(2) 2.8775(8) yes . 3_756 O(2) C(4) 3.113(4) yes . 3_756 O(2) C(5) 3.288(4) yes . 3_756 O(2) C(8) 3.332(4) yes . 3_756 O(3) Cl(2) 3.527(3) yes . 1_554 O(3) N(2) 2.766(5) yes . 3_755 O(4) Cl(3) 3.464(2) yes . 4_555 O(4) C(17) 3.246(3) yes . 4_555 O(4) C(18) 3.506(4) yes . 4_555 N(1) Cl(3) 3.451(4) yes . 2_745 N(1) C(26) 3.581(5) yes . 2_645 N(2) Cl(2) 3.448(4) yes . 3_756 N(2) Cl(3) 3.231(4) yes . 3_755 N(2) Cl(4) 3.585(3) yes . 2_745 N(2) O(3) 2.766(5) yes . 3_755 N(3) N(3) 3.5878(12) yes . 3_655 N(3) C(9) 3.335(5) yes . . N(4) Cl(1) 3.225(4) yes . 3_656 N(4) O(1) 2.772(4) yes . 3_656 C(1) C(12) 3.489(5) yes . 3_756 C(1) C(13) 3.514(5) yes . 3_756 C(1) C(25) 3.498(4) yes . 2_645 C(1) C(30) 3.381(4) yes . 2_645 C(2) C(12) 3.577(5) yes . 3_756 C(2) C(30) 3.576(5) yes . 2_645 C(4) O(2) 3.113(4) yes . 3_756 C(5) O(2) 3.288(4) yes . 3_756 C(7) C(26) 3.416(5) yes . 2_645 C(8) O(2) 3.332(4) yes . 3_756 C(9) N(3) 3.335(5) yes . . C(9) C(22) 3.468(5) yes . . C(11) C(11) 3.5043(10) yes . 3_755 C(12) C(1) 3.489(5) yes . 3_756 C(12) C(2) 3.577(5) yes . 3_756 C(13) O(1) 3.349(4) yes . 3_756 C(13) C(1) 3.514(5) yes . 3_756 C(15) C(16) 3.457(4) yes . . C(15) C(21) 3.499(5) yes . . C(16) C(15) 3.457(4) yes . . C(17) O(4) 3.246(3) yes . 4_554 C(18) O(4) 3.506(4) yes . 4_554 C(21) C(15) 3.499(5) yes . . C(21) C(29) 3.541(5) yes . 4_554 C(21) C(30) 3.577(4) yes . 4_554 C(22) C(9) 3.468(5) yes . . C(22) C(29) 3.346(5) yes . 4_554 C(23) C(28) 3.588(5) yes . 4_554 C(24) O(1) 3.194(4) yes . 2_655 C(25) O(1) 3.355(4) yes . 2_655 C(25) C(1) 3.498(4) yes . 2_655 C(26) N(1) 3.581(5) yes . 2_655 C(26) C(7) 3.416(5) yes . 2_655 C(28) C(23) 3.588(5) yes . 4_555 C(29) C(21) 3.541(5) yes . 4_555 C(29) C(22) 3.346(5) yes . 4_555 C(30) O(1) 3.596(4) yes . 2_655 C(30) C(1) 3.381(4) yes . 2_655 C(30) C(2) 3.576(5) yes . 2_655 C(30) C(21) 3.577(4) yes . 4_555 Cl(1) H(1) 2.4633 yes . . Cl(2) H(9A) 2.9404 yes . . Cl(3) H(3) 2.4928 yes . . Cl(4) H(24B) 2.9385 yes . . O(2) H(11) 3.1500 yes . . O(2) H(15) 3.3438 yes . . O(4) H(26) 3.2137 yes . . O(4) H(30) 3.3405 yes . . N(2) H(9B) 3.3013 yes . . N(2) H(11) 3.0903 yes . . N(4) H(24A) 3.4323 yes . . N(4) H(26) 3.1498 yes . . C(2) H(1) 2.4118 yes . . C(3) H(9A) 3.0796 yes . . C(3) H(9B) 3.5276 yes . . C(4) H(9A) 2.6391 yes . . C(4) H(9B) 2.5456 yes . . C(5) H(9B) 3.0248 yes . . C(6) H(1) 3.0137 yes . . C(7) H(1) 3.5131 yes . . C(8) H(9B) 2.9465 yes . . C(8) H(11) 3.4928 yes . . C(9) H(11) 2.6389 yes . . C(9) H(15) 2.6564 yes . . C(10) H(12) 3.2379 yes . . C(10) H(14) 3.2292 yes . . C(11) H(9A) 3.2620 yes . . C(11) H(9B) 2.6227 yes . . C(11) H(13) 3.2357 yes . . C(11) H(15) 3.2128 yes . . C(12) H(14) 3.2119 yes . . C(13) H(11) 3.2350 yes . . C(13) H(15) 3.1990 yes . . C(14) H(12) 3.2089 yes . . C(15) H(9A) 2.5986 yes . . C(15) H(9B) 3.2342 yes . . C(15) H(11) 3.2139 yes . . C(15) H(13) 3.2056 yes . . C(17) H(3) 2.4265 yes . . C(18) H(24A) 3.4878 yes . . C(18) H(24B) 3.0767 yes . . C(19) H(24A) 2.5335 yes . . C(19) H(24B) 2.6567 yes . . C(20) H(24A) 3.0436 yes . . C(21) H(3) 3.0051 yes . . C(22) H(3) 3.4966 yes . . C(23) H(24A) 3.0454 yes . . C(23) H(26) 3.5383 yes . . C(24) H(26) 2.6346 yes . . C(24) H(30) 2.6594 yes . . C(25) H(27) 3.2375 yes . . C(25) H(29) 3.2353 yes . . C(26) H(24A) 2.6037 yes . . C(26) H(24B) 3.2448 yes . . C(26) H(28) 3.2257 yes . . C(26) H(30) 3.2145 yes . . C(27) H(29) 3.2113 yes . . C(28) H(26) 3.2233 yes . . C(28) H(30) 3.2016 yes . . C(29) H(27) 3.2107 yes . . C(30) H(24A) 3.2392 yes . . C(30) H(24B) 2.5964 yes . . C(30) H(26) 3.2155 yes . . C(30) H(28) 3.2059 yes . . H(9A) H(11) 3.5299 yes . . H(9A) H(15) 2.4240 yes . . H(9B) H(11) 2.4770 yes . . H(9B) H(15) 3.4911 yes . . H(11) H(12) 2.3184 yes . . H(12) H(13) 2.3267 yes . . H(13) H(14) 2.2813 yes . . H(14) H(15) 2.2991 yes . . H(24A) H(26) 2.4475 yes . . H(24A) H(30) 3.5011 yes . . H(24B) H(26) 3.5104 yes . . H(24B) H(30) 2.4291 yes . . H(26) H(27) 2.3113 yes . . H(27) H(28) 2.3212 yes . . H(28) H(29) 2.2842 yes . . H(29) H(30) 2.2975 yes . . Cl(1) H(12) 3.5118 yes . 3_756 Cl(1) H(29) 3.2229 yes . 4_555 Cl(1) H(30) 3.2966 yes . 4_555 Cl(2) H(3) 3.5232 yes . 1_556 Cl(2) H(30) 3.1156 yes . 4_555 Cl(3) H(14) 3.1758 yes . 4_554 Cl(3) H(15) 3.4187 yes . 4_554 Cl(4) H(15) 3.1856 yes . 4_554 O(1) H(13) 3.2654 yes . 3_756 O(1) H(24A) 3.0506 yes . 2_645 O(1) H(24B) 2.7785 yes . 2_645 O(1) H(26) 3.0770 yes . 3_656 O(3) H(11) 3.0478 yes . 3_755 N(1) H(13) 3.0041 yes . 2_745 N(1) H(14) 3.0639 yes . 2_745 N(1) H(26) 3.3395 yes . 2_645 N(1) H(27) 2.9426 yes . 3_656 N(2) H(3) 2.0288 yes . 3_755 N(3) H(9A) 2.8073 yes . . N(3) H(9B) 3.0430 yes . . N(3) H(12) 3.0355 yes . 3_755 N(3) H(28) 3.0866 yes . 2_645 N(3) H(29) 3.0727 yes . 2_645 N(3) H(29) 3.0966 yes . 4_554 N(4) H(1) 2.0349 yes . 3_656 N(4) H(24B) 3.0324 yes . 4_555 N(4) H(28) 3.5106 yes . 4_554 C(1) H(24B) 3.5581 yes . 2_645 C(1) H(30) 3.5020 yes . 2_645 C(2) H(12) 3.5797 yes . 3_756 C(2) H(30) 3.4596 yes . 2_645 C(7) H(14) 3.5872 yes . 3_756 C(7) H(26) 3.4758 yes . 2_645 C(7) H(27) 3.5938 yes . 3_656 C(8) H(3) 3.1450 yes . 3_755 C(11) H(11) 3.2023 yes . 3_755 C(12) H(9B) 3.4165 yes . 3_755 C(12) H(11) 3.3501 yes . 3_755 C(12) H(28) 3.4536 yes . 4_654 C(13) H(1) 3.4735 yes . 3_756 C(13) H(28) 3.5480 yes . 4_654 C(16) H(15) 3.4154 yes . . C(17) H(14) 3.3749 yes . . C(20) H(15) 3.3614 yes . . C(21) H(9A) 3.4496 yes . . C(21) H(15) 3.1783 yes . . C(22) H(9A) 2.8461 yes . . C(22) H(9B) 3.4461 yes . . C(22) H(29) 3.0961 yes . 4_554 C(23) H(1) 3.1428 yes . 3_656 C(23) H(28) 3.5834 yes . 4_554 C(24) H(1) 3.3663 yes . 2_655 C(26) H(24A) 3.1560 yes . 4_555 C(27) H(13) 3.5161 yes . 4_455 C(27) H(24A) 3.0241 yes . 4_555 C(28) H(9B) 3.5109 yes . 2_655 C(28) H(13) 3.5808 yes . 4_455 H(1) N(4) 2.0349 yes . 3_656 H(1) C(13) 3.4735 yes . 3_756 H(1) C(23) 3.1428 yes . 3_656 H(1) C(24) 3.3663 yes . 2_645 H(1) H(12) 3.5242 yes . 3_756 H(1) H(13) 3.2797 yes . 3_756 H(1) H(24A) 3.3549 yes . 2_645 H(1) H(24B) 2.7248 yes . 2_645 H(1) H(26) 3.1447 yes . 3_656 H(1) H(30) 3.5892 yes . 2_645 H(3) Cl(2) 3.5232 yes . 1_554 H(3) N(2) 2.0288 yes . 3_755 H(3) C(8) 3.1450 yes . 3_755 H(3) H(11) 3.0197 yes . 3_755 H(9A) N(3) 2.8073 yes . . H(9A) C(21) 3.4496 yes . . H(9A) C(22) 2.8461 yes . . H(9A) H(29) 3.5916 yes . 2_645 H(9B) N(3) 3.0430 yes . . H(9B) C(12) 3.4165 yes . 3_755 H(9B) C(22) 3.4461 yes . . H(9B) C(28) 3.5109 yes . 2_645 H(9B) H(12) 2.8491 yes . 3_755 H(9B) H(28) 2.9595 yes . 2_645 H(11) O(3) 3.0478 yes . 3_755 H(11) C(11) 3.2023 yes . 3_755 H(11) C(12) 3.3501 yes . 3_755 H(11) H(3) 3.0197 yes . 3_755 H(11) H(11) 3.1616 yes . 3_755 H(11) H(12) 3.4134 yes . 3_755 H(12) Cl(1) 3.5118 yes . 3_756 H(12) N(3) 3.0355 yes . 3_755 H(12) C(2) 3.5797 yes . 3_756 H(12) H(1) 3.5242 yes . 3_756 H(12) H(9B) 2.8491 yes . 3_755 H(12) H(11) 3.4134 yes . 3_755 H(12) H(28) 2.7873 yes . 4_654 H(13) O(1) 3.2654 yes . 3_756 H(13) N(1) 3.0041 yes . 2_755 H(13) C(27) 3.5161 yes . 4_654 H(13) C(28) 3.5808 yes . 4_654 H(13) H(1) 3.2797 yes . 3_756 H(13) H(27) 2.8459 yes . 4_654 H(13) H(28) 2.9740 yes . 4_654 H(14) Cl(3) 3.1758 yes . 4_555 H(14) N(1) 3.0639 yes . 2_755 H(14) C(7) 3.5872 yes . 3_756 H(14) C(17) 3.3749 yes . . H(15) Cl(3) 3.4187 yes . 4_555 H(15) Cl(4) 3.1856 yes . 4_555 H(15) C(16) 3.4154 yes . . H(15) C(20) 3.3614 yes . . H(15) C(21) 3.1783 yes . . H(24A) O(1) 3.0506 yes . 2_655 H(24A) C(26) 3.1560 yes . 4_554 H(24A) C(27) 3.0241 yes . 4_554 H(24A) H(1) 3.3549 yes . 2_655 H(24A) H(26) 3.0575 yes . 4_554 H(24A) H(27) 2.8290 yes . 4_554 H(24B) O(1) 2.7785 yes . 2_655 H(24B) N(4) 3.0324 yes . 4_554 H(24B) C(1) 3.5581 yes . 2_655 H(24B) H(1) 2.7248 yes . 2_655 H(24B) H(26) 3.5240 yes . 4_554 H(26) O(1) 3.0770 yes . 3_656 H(26) N(1) 3.3395 yes . 2_655 H(26) C(7) 3.4758 yes . 2_655 H(26) H(1) 3.1447 yes . 3_656 H(26) H(24A) 3.0575 yes . 4_555 H(26) H(24B) 3.5240 yes . 4_555 H(27) N(1) 2.9426 yes . 3_656 H(27) C(7) 3.5938 yes . 3_656 H(27) H(13) 2.8459 yes . 4_455 H(27) H(24A) 2.8290 yes . 4_555 H(28) N(3) 3.0866 yes . 2_655 H(28) N(4) 3.5106 yes . 4_555 H(28) C(12) 3.4536 yes . 4_455 H(28) C(13) 3.5480 yes . 4_455 H(28) C(23) 3.5834 yes . 4_555 H(28) H(9B) 2.9595 yes . 2_655 H(28) H(12) 2.7873 yes . 4_455 H(28) H(13) 2.9740 yes . 4_455 H(29) Cl(1) 3.2229 yes . 4_554 H(29) N(3) 3.0727 yes . 2_655 H(29) N(3) 3.0966 yes . 4_555 H(29) C(22) 3.0961 yes . 4_555 H(29) H(9A) 3.5916 yes . 2_655 H(30) Cl(1) 3.2966 yes . 4_554 H(30) Cl(2) 3.1156 yes . 4_554 H(30) C(1) 3.5020 yes . 2_655 H(30) C(2) 3.4596 yes . 2_655 H(30) H(1) 3.5892 yes . 2_655 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) Cl(1) . . . 2.969(2) 0.830 2.463 120 no O(1) H(1) N(4) . . 3_656 2.772(4) 0.830 2.035 148 no O(3) H(3) Cl(3) . . . 2.983(3) 0.830 2.493 119 no O(3) H(3) N(2) . . 3_755 2.766(5) 0.830 2.029 148 no #============================================================================== # End of CIF #==============================================================================