#========================================================================== data_global #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '16 July 2006' #========================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #========================================================================== # SUBMISSION DETAILS _publ_contact_letter ; Date of submission: 2006-07-16 Please consider this CIF submission for publication in Green Chemistry. All authors have seen and approved this submission. The CIF has passed the Chester CHECKCIF routines and gives a satisfactory PRINTCIF file. Best wishes, Guanwu Wang ; _publ_contact_author_name 'Dr. Guanwu Wang' _publ_contact_author_address ; Department of Chemistry University of Science and Technology of China Hefei 230026 P.R.China ; _publ_contact_author_email gwang@ustc.edu.cn _publ_contact_author_fax '86 551 360 7864' _publ_contact_author_phone '86 551 360 7864' _publ_requested_journal 'Green Chemistry' _publ_requested_category EO _publ_requested_coeditor_name ? #========================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Benign one-pot multi-component approaches to the synthesis of novel unsymmetrical 4-arylacridinediones ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_address 'Guanwu Wang' ; Department of Chemistry University of Science and Technology of China Hefei 230026 P.R.China ; 'Chunbao Miao' ; Department of Chemistry University of Science and Technology of China Hefei 230026 P.R.China ; #========================================================================== # TEXT _publ_section_abstract ; A synthetic route to unsymmetrical 4-arylacridinediones in aqueous-phase or solvent-free conditions is described. These aqueous and solvent-free conditions give excellent yields that could not be achieved in organic solvents. The current process provides a simple and green method to obtain a variety of novel unsymmetrical acridinediones, which may have potential biological activities. ; #========================================================================== data_I #========================================================================== # CHEMICAL DATA _chemical_name_systematic ; 1,8-dioxo-3, 3-dimethyl-9-(4-Chloro-phenyl)- 1,2,3,4,5,6,7,8,9,10-decahydroacridine ; _chemical_name_common ? _chemical_melting_point 511k _chemical_formula_moiety 'C21 H22 Cl N O2' _chemical_formula_sum 'C21 H22 Cl N O2' _chemical_formula_weight 355.85 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1209(8) _cell_length_b 16.3999(19) _cell_length_c 15.0997(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.716(4) _cell_angle_gamma 90.00 _cell_volume 1761.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6559 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description 'block' _exptl_crystal_colour 'light-Yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9132 _exptl_absorpt_correction_T_max 0.9552 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17172 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3230 _reflns_number_gt 2957 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear' _computing_cell_refinement 'CrystalClear' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+0.8248P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3230 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Cl1 Cl 0.34520(9) 0.42029(3) 0.54182(3) 0.05080(18) Uani 1 1 d . . . O1 O 0.42829(16) 0.06404(7) 0.30124(8) 0.0346(3) Uani 1 1 d . . . O2 O 0.20215(15) 0.29775(7) 0.11080(8) 0.0317(3) Uani 1 1 d . . . N1 N 0.84095(18) 0.22956(8) 0.14637(9) 0.0245(3) Uani 1 1 d . . . H1 H 0.9588 0.2420 0.1376 0.029 Uiso 1 1 calc R . . C1 C 0.8003(2) 0.15974(9) 0.19293(10) 0.0218(3) Uani 1 1 d . . . C2 C 0.6290(2) 0.15018(9) 0.22658(10) 0.0214(3) Uani 1 1 d . . . C3 C 0.4789(2) 0.21542(9) 0.21758(10) 0.0218(3) Uani 1 1 d . . . H3 H 0.3575 0.1874 0.2013 0.026 Uiso 1 1 calc R . . C4 C 0.5218(2) 0.27147(9) 0.14133(10) 0.0209(3) Uani 1 1 d . . . C5 C 0.6998(2) 0.27990(9) 0.11355(10) 0.0212(3) Uani 1 1 d . . . C6 C 0.5788(2) 0.07244(10) 0.26591(10) 0.0238(3) Uani 1 1 d . . . C7 C 0.7131(2) 0.00212(10) 0.25780(12) 0.0292(4) Uani 1 1 d . . . H7A H 0.6857 -0.0255 0.2003 0.035 Uiso 1 1 calc R . . H7B H 0.6909 -0.0377 0.3054 0.035 Uiso 1 1 calc R . . C8 C 0.9208(2) 0.02715(9) 0.26360(11) 0.0247(4) Uani 1 1 d . . . C9 C 0.9499(2) 0.09484(10) 0.19568(11) 0.0250(4) Uani 1 1 d . . . H9A H 1.0732 0.1209 0.2094 0.030 Uiso 1 1 calc R . . H9B H 0.9543 0.0699 0.1361 0.030 Uiso 1 1 calc R . . C10 C 0.3670(2) 0.31216(9) 0.09400(10) 0.0223(3) Uani 1 1 d . . . C11 C 0.4108(2) 0.37074(10) 0.02088(11) 0.0259(4) Uani 1 1 d . . . H11A H 0.3175 0.4156 0.0196 0.031 Uiso 1 1 calc R . . H11B H 0.3984 0.3419 -0.0367 0.031 Uiso 1 1 calc R . . C12 C 0.6073(2) 0.40680(9) 0.03206(11) 0.0248(4) Uani 1 1 d . . . H12A H 0.6153 0.4425 0.0850 0.030 Uiso 1 1 calc R . . H12B H 0.6340 0.4402 -0.0204 0.030 Uiso 1 1 calc R . . C13 C 0.7515(2) 0.33861(10) 0.04267(11) 0.0245(3) Uani 1 1 d . . . H13A H 0.7593 0.3092 -0.0143 0.029 Uiso 1 1 calc R . . H13B H 0.8767 0.3623 0.0581 0.029 Uiso 1 1 calc R . . C14 C 0.4496(2) 0.26433(9) 0.30160(10) 0.0236(3) Uani 1 1 d . . . C15 C 0.5956(2) 0.30677(11) 0.34461(11) 0.0303(4) Uani 1 1 d . . . H15 H 0.7184 0.3033 0.3228 0.036 Uiso 1 1 calc R . . C16 C 0.5663(3) 0.35429(11) 0.41886(12) 0.0361(4) Uani 1 1 d . . . H16 H 0.6675 0.3831 0.4476 0.043 Uiso 1 1 calc R . . C17 C 0.3871(3) 0.35899(10) 0.45028(11) 0.0341(4) Uani 1 1 d . . . C18 C 0.2400(3) 0.31679(11) 0.40969(12) 0.0351(4) Uani 1 1 d . . . H18 H 0.1179 0.3197 0.4323 0.042 Uiso 1 1 calc R . . C19 C 0.2718(2) 0.27001(11) 0.33553(12) 0.0301(4) Uani 1 1 d . . . H19 H 0.1700 0.2412 0.3072 0.036 Uiso 1 1 calc R . . C20 C 1.0432(2) -0.04622(10) 0.24201(13) 0.0337(4) Uani 1 1 d . . . H20A H 1.0164 -0.0914 0.2820 0.051 Uiso 1 1 calc R . . H20B H 1.1761 -0.0311 0.2497 0.051 Uiso 1 1 calc R . . H20C H 1.0155 -0.0631 0.1805 0.051 Uiso 1 1 calc R . . C21 C 0.9755(2) 0.05754(12) 0.35712(11) 0.0330(4) Uani 1 1 d . . . H21A H 0.8995 0.1054 0.3706 0.050 Uiso 1 1 calc R . . H21B H 1.1089 0.0724 0.3605 0.050 Uiso 1 1 calc R . . H21C H 0.9530 0.0143 0.4001 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0785(4) 0.0409(3) 0.0345(3) -0.0044(2) 0.0186(2) 0.0112(2) O1 0.0250(6) 0.0326(7) 0.0470(8) 0.0115(6) 0.0120(5) -0.0023(5) O2 0.0176(6) 0.0365(7) 0.0412(7) 0.0085(5) 0.0032(5) -0.0005(5) N1 0.0153(6) 0.0260(7) 0.0326(7) 0.0059(6) 0.0057(5) -0.0015(5) C1 0.0197(8) 0.0232(8) 0.0226(8) 0.0011(6) 0.0014(6) -0.0015(6) C2 0.0190(7) 0.0223(8) 0.0230(8) 0.0005(6) 0.0027(6) -0.0002(6) C3 0.0165(7) 0.0233(8) 0.0258(8) 0.0029(6) 0.0035(6) -0.0012(6) C4 0.0192(7) 0.0207(7) 0.0230(8) 0.0005(6) 0.0025(6) -0.0020(6) C5 0.0205(8) 0.0210(8) 0.0222(8) -0.0003(6) 0.0014(6) -0.0021(6) C6 0.0205(8) 0.0251(8) 0.0258(8) 0.0016(7) 0.0008(6) -0.0028(6) C7 0.0247(8) 0.0217(8) 0.0413(10) 0.0033(7) 0.0014(7) -0.0015(7) C8 0.0213(8) 0.0222(8) 0.0307(9) 0.0013(7) 0.0028(7) 0.0021(6) C9 0.0202(8) 0.0264(8) 0.0287(8) -0.0010(7) 0.0060(6) 0.0012(6) C10 0.0205(8) 0.0221(8) 0.0243(8) -0.0030(6) 0.0021(6) -0.0016(6) C11 0.0242(8) 0.0257(8) 0.0277(8) 0.0046(7) -0.0007(7) 0.0000(6) C12 0.0249(8) 0.0217(8) 0.0280(8) 0.0039(7) 0.0035(7) -0.0014(6) C13 0.0214(8) 0.0258(8) 0.0266(8) 0.0035(7) 0.0053(6) -0.0020(6) C14 0.0250(8) 0.0224(8) 0.0237(8) 0.0076(6) 0.0051(7) 0.0038(6) C15 0.0268(9) 0.0319(9) 0.0327(9) -0.0008(7) 0.0063(7) 0.0004(7) C16 0.0410(10) 0.0334(10) 0.0339(10) -0.0038(8) 0.0022(8) -0.0013(8) C17 0.0510(11) 0.0275(9) 0.0246(9) 0.0042(7) 0.0105(8) 0.0114(8) C18 0.0350(10) 0.0362(10) 0.0353(10) 0.0079(8) 0.0152(8) 0.0104(8) C19 0.0255(9) 0.0321(9) 0.0331(9) 0.0050(7) 0.0071(7) 0.0042(7) C20 0.0285(9) 0.0269(9) 0.0459(11) -0.0014(8) 0.0019(8) 0.0041(7) C21 0.0278(9) 0.0413(10) 0.0299(9) 0.0005(8) 0.0011(7) 0.0044(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C17 1.7462(17) . ? O1 C6 1.2272(19) . ? O2 C10 1.2352(18) . ? N1 C5 1.375(2) . ? N1 C1 1.381(2) . ? N1 H1 0.8800 . ? C1 C2 1.353(2) . ? C1 C9 1.505(2) . ? C2 C6 1.458(2) . ? C2 C3 1.514(2) . ? C3 C4 1.516(2) . ? C3 C14 1.524(2) . ? C3 H3 1.0000 . ? C4 C5 1.361(2) . ? C4 C10 1.448(2) . ? C5 C13 1.499(2) . ? C6 C7 1.507(2) . ? C7 C8 1.533(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C20 1.530(2) . ? C8 C21 1.530(2) . ? C8 C9 1.532(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.507(2) . ? C11 C12 1.521(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.387(2) . ? C14 C19 1.391(2) . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 C17 1.384(3) . ? C16 H16 0.9500 . ? C17 C18 1.375(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C5 N1 C1 120.93(13) . . ? C5 N1 H1 119.5 . . ? C1 N1 H1 119.5 . . ? C2 C1 N1 120.11(14) . . ? C2 C1 C9 123.87(14) . . ? N1 C1 C9 115.80(13) . . ? C1 C2 C6 119.82(14) . . ? C1 C2 C3 121.98(14) . . ? C6 C2 C3 117.96(13) . . ? C2 C3 C4 109.28(12) . . ? C2 C3 C14 114.92(13) . . ? C4 C3 C14 110.72(13) . . ? C2 C3 H3 107.2 . . ? C4 C3 H3 107.2 . . ? C14 C3 H3 107.2 . . ? C5 C4 C10 119.98(14) . . ? C5 C4 C3 121.30(14) . . ? C10 C4 C3 118.59(13) . . ? C4 C5 N1 120.24(14) . . ? C4 C5 C13 123.31(14) . . ? N1 C5 C13 116.31(13) . . ? O1 C6 C2 120.74(14) . . ? O1 C6 C7 121.35(14) . . ? C2 C6 C7 117.85(13) . . ? C6 C7 C8 113.87(13) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C20 C8 C21 109.27(14) . . ? C20 C8 C9 109.31(13) . . ? C21 C8 C9 110.19(14) . . ? C20 C8 C7 109.57(13) . . ? C21 C8 C7 110.03(14) . . ? C9 C8 C7 108.45(13) . . ? C1 C9 C8 114.39(13) . . ? C1 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C1 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? O2 C10 C4 121.27(14) . . ? O2 C10 C11 120.26(14) . . ? C4 C10 C11 118.43(13) . . ? C10 C11 C12 112.80(13) . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 109.81(13) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C5 C13 C12 111.09(13) . . ? C5 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C5 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C19 117.98(15) . . ? C15 C14 C3 121.66(14) . . ? C19 C14 C3 120.32(14) . . ? C14 C15 C16 121.40(16) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 118.97(17) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C18 C17 C16 120.93(16) . . ? C18 C17 Cl1 119.18(14) . . ? C16 C17 Cl1 119.88(15) . . ? C17 C18 C19 119.27(16) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C14 121.42(17) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? C8 C20 H20A 109.5 . . ? C8 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C8 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 C21 H21A 109.5 . . ? C8 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C8 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C5 N1 C1 C2 -17.0(2) . . . . ? C5 N1 C1 C9 157.85(14) . . . . ? N1 C1 C2 C6 172.36(14) . . . . ? C9 C1 C2 C6 -2.0(2) . . . . ? N1 C1 C2 C3 -2.0(2) . . . . ? C9 C1 C2 C3 -176.39(14) . . . . ? C1 C2 C3 C4 20.8(2) . . . . ? C6 C2 C3 C4 -153.62(13) . . . . ? C1 C2 C3 C14 -104.32(17) . . . . ? C6 C2 C3 C14 81.22(17) . . . . ? C2 C3 C4 C5 -24.1(2) . . . . ? C14 C3 C4 C5 103.43(17) . . . . ? C2 C3 C4 C10 151.70(13) . . . . ? C14 C3 C4 C10 -80.74(17) . . . . ? C10 C4 C5 N1 -167.11(14) . . . . ? C3 C4 C5 N1 8.7(2) . . . . ? C10 C4 C5 C13 8.5(2) . . . . ? C3 C4 C5 C13 -175.75(14) . . . . ? C1 N1 C5 C4 13.5(2) . . . . ? C1 N1 C5 C13 -162.35(14) . . . . ? C1 C2 C6 O1 175.86(15) . . . . ? C3 C2 C6 O1 -9.6(2) . . . . ? C1 C2 C6 C7 -7.0(2) . . . . ? C3 C2 C6 C7 167.58(14) . . . . ? O1 C6 C7 C8 -146.92(16) . . . . ? C2 C6 C7 C8 36.0(2) . . . . ? C6 C7 C8 C20 -172.29(14) . . . . ? C6 C7 C8 C21 67.55(18) . . . . ? C6 C7 C8 C9 -53.04(18) . . . . ? C2 C1 C9 C8 -18.1(2) . . . . ? N1 C1 C9 C8 167.26(13) . . . . ? C20 C8 C9 C1 163.34(14) . . . . ? C21 C8 C9 C1 -76.57(17) . . . . ? C7 C8 C9 C1 43.92(18) . . . . ? C5 C4 C10 O2 170.99(15) . . . . ? C3 C4 C10 O2 -4.9(2) . . . . ? C5 C4 C10 C11 -6.8(2) . . . . ? C3 C4 C10 C11 177.31(14) . . . . ? O2 C10 C11 C12 157.24(15) . . . . ? C4 C10 C11 C12 -24.9(2) . . . . ? C10 C11 C12 C13 53.59(18) . . . . ? C4 C5 C13 C12 21.7(2) . . . . ? N1 C5 C13 C12 -162.59(13) . . . . ? C11 C12 C13 C5 -51.35(18) . . . . ? C2 C3 C14 C15 57.1(2) . . . . ? C4 C3 C14 C15 -67.26(18) . . . . ? C2 C3 C14 C19 -125.30(15) . . . . ? C4 C3 C14 C19 110.29(16) . . . . ? C19 C14 C15 C16 -0.6(2) . . . . ? C3 C14 C15 C16 177.01(15) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C15 C16 C17 C18 0.7(3) . . . . ? C15 C16 C17 Cl1 -178.41(14) . . . . ? C16 C17 C18 C19 -1.0(3) . . . . ? Cl1 C17 C18 C19 178.14(13) . . . . ? C17 C18 C19 C14 0.5(3) . . . . ? C15 C14 C19 C18 0.3(2) . . . . ? C3 C14 C19 C18 -177.32(15) . . . . ? 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 N1 H1 O2 0.88 2.02 2.8785(17) 165.9 1_655 C20 H20B O1 0.98 2.48 3.370(2) 151.4 1_655 C21 H21B O1 0.98 2.49 3.373(2) 150.3 1_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.220 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.040