# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Song Ye' _publ_contact_author_email songye@iccas.ac.cn loop_ _publ_author_name 'Li-Hui Sun' 'Li-Tao Shen' 'Song Ye' data_mx958 _database_code_depnum_ccdc_archive 'CCDC 831812' #TrackingRef 'web_deposit_cif_file_0_SongYe_1309230164.mx958.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H18 Cl N O3' _chemical_formula_sum 'C24 H18 Cl N O3' _chemical_formula_weight 403.84 _chemical_absolute_configuration ad 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.1336(12) _cell_length_b 13.2540(18) _cell_length_c 16.646(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2015.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7004 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18181 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4602 _reflns_number_gt 4351 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0429P)^2^+1.0597P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(7) _refine_ls_number_reflns 4602 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.26427(8) 0.72589(5) 0.21602(4) 0.04454(18) Uani 1 1 d . . . O1 O 0.63438(17) 0.22776(12) 0.01662(9) 0.0292(4) Uani 1 1 d . . . O2 O 0.7595(2) 0.36649(13) 0.13610(10) 0.0365(4) Uani 1 1 d . . . O3 O 0.5849(2) 0.08430(12) 0.08070(11) 0.0384(4) Uani 1 1 d . . . N1 N 0.7633(2) 0.46794(14) 0.02375(11) 0.0275(4) Uani 1 1 d . . . C1 C 0.5950(3) 0.33343(16) 0.02202(13) 0.0254(5) Uani 1 1 d . . . C2 C 0.7154(3) 0.38922(16) 0.06984(14) 0.0269(5) Uani 1 1 d . . . C3 C 0.7000(3) 0.46408(17) -0.05410(14) 0.0282(5) Uani 1 1 d . . . C4 C 0.6013(3) 0.38446(17) -0.05815(14) 0.0281(5) Uani 1 1 d . . . C5 C 0.5286(3) 0.3637(2) -0.12907(15) 0.0381(6) Uani 1 1 d . . . H5A H 0.4603 0.3098 -0.1324 0.046 Uiso 1 1 calc R . . C6 C 0.5585(4) 0.4244(2) -0.19579(16) 0.0474(7) Uani 1 1 d . . . H6A H 0.5111 0.4110 -0.2454 0.057 Uiso 1 1 calc R . . C7 C 0.6559(4) 0.5033(2) -0.19034(16) 0.0459(7) Uani 1 1 d . . . H7A H 0.6738 0.5439 -0.2363 0.055 Uiso 1 1 calc R . . C8 C 0.7287(3) 0.52498(19) -0.11918(15) 0.0380(6) Uani 1 1 d . . . H8A H 0.7956 0.5797 -0.1156 0.046 Uiso 1 1 calc R . . C9 C 0.4443(3) 0.33281(17) 0.06454(14) 0.0273(5) Uani 1 1 d . . . H9A H 0.3689 0.3181 0.0226 0.033 Uiso 1 1 calc R . . C10 C 0.4562(3) 0.23922(17) 0.11754(15) 0.0308(5) Uani 1 1 d . . . H10A H 0.4948 0.2567 0.1713 0.037 Uiso 1 1 calc R . . H10B H 0.3598 0.2061 0.1238 0.037 Uiso 1 1 calc R . . C11 C 0.5611(3) 0.17242(18) 0.07301(14) 0.0289(5) Uani 1 1 d . . . C12 C 0.4018(3) 0.43070(17) 0.10388(14) 0.0271(5) Uani 1 1 d . . . C13 C 0.4343(3) 0.45227(19) 0.18365(15) 0.0367(6) Uani 1 1 d . . . H13A H 0.4864 0.4042 0.2149 0.044 Uiso 1 1 calc R . . C14 C 0.3923(3) 0.54250(19) 0.21833(16) 0.0403(6) Uani 1 1 d . . . H14A H 0.4136 0.5560 0.2731 0.048 Uiso 1 1 calc R . . C15 C 0.3188(3) 0.61269(18) 0.17212(16) 0.0344(6) Uani 1 1 d . . . C16 C 0.2879(3) 0.59491(19) 0.09212(16) 0.0368(6) Uani 1 1 d . . . H16A H 0.2395 0.6444 0.0605 0.044 Uiso 1 1 calc R . . C17 C 0.3290(3) 0.50320(19) 0.05897(16) 0.0343(6) Uani 1 1 d . . . H17A H 0.3068 0.4897 0.0043 0.041 Uiso 1 1 calc R . . C18 C 0.8731(3) 0.54021(18) 0.04989(15) 0.0316(5) Uani 1 1 d . . . H18A H 0.9453 0.5494 0.0062 0.038 Uiso 1 1 calc R . . H18B H 0.9257 0.5119 0.0967 0.038 Uiso 1 1 calc R . . C19 C 0.8119(3) 0.64230(18) 0.07272(15) 0.0320(5) Uani 1 1 d . . . C20 C 0.6627(4) 0.6647(2) 0.0708(3) 0.0635(10) Uani 1 1 d . . . H20A H 0.5950 0.6147 0.0538 0.076 Uiso 1 1 calc R . . C21 C 0.6120(4) 0.7591(2) 0.0933(3) 0.0755(13) Uani 1 1 d . . . H21A H 0.5101 0.7731 0.0916 0.091 Uiso 1 1 calc R . . C22 C 0.7085(4) 0.8330(2) 0.11838(18) 0.0528(8) Uani 1 1 d . . . H22A H 0.6735 0.8967 0.1361 0.063 Uiso 1 1 calc R . . C23 C 0.8529(4) 0.8132(2) 0.1172(3) 0.0705(11) Uani 1 1 d . . . H23A H 0.9207 0.8644 0.1317 0.085 Uiso 1 1 calc R . . C24 C 0.9037(4) 0.7183(2) 0.0949(2) 0.0612(10) Uani 1 1 d . . . H24A H 1.0062 0.7061 0.0951 0.073 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 0.0508(4) 0.0306(3) 0.0522(4) -0.0131(3) 0.0047(3) 0.0082(3) O1 0.0324(9) 0.0233(8) 0.0318(8) -0.0014(7) 0.0074(7) 0.0001(7) O2 0.0390(10) 0.0395(9) 0.0309(8) 0.0050(7) -0.0101(8) -0.0076(8) O3 0.0537(11) 0.0220(8) 0.0395(10) -0.0021(7) 0.0020(9) 0.0013(8) N1 0.0300(10) 0.0234(9) 0.0292(9) -0.0014(8) -0.0009(9) -0.0028(8) C1 0.0291(11) 0.0214(10) 0.0256(10) -0.0034(9) -0.0011(9) 0.0000(9) C2 0.0267(11) 0.0249(11) 0.0291(11) -0.0019(9) 0.0012(9) 0.0015(9) C3 0.0303(12) 0.0258(11) 0.0284(11) -0.0018(9) 0.0011(9) 0.0003(9) C4 0.0326(12) 0.0259(11) 0.0259(11) -0.0018(9) 0.0036(10) -0.0003(9) C5 0.0446(15) 0.0392(14) 0.0304(12) -0.0045(11) -0.0008(12) -0.0075(12) C6 0.0606(18) 0.0540(17) 0.0276(13) 0.0024(12) -0.0063(13) -0.0074(15) C7 0.0634(19) 0.0467(16) 0.0277(13) 0.0084(12) 0.0030(13) -0.0056(15) C8 0.0462(15) 0.0324(13) 0.0354(13) 0.0043(10) 0.0011(12) -0.0044(12) C9 0.0274(11) 0.0243(11) 0.0301(11) -0.0049(9) 0.0008(9) -0.0027(9) C10 0.0340(12) 0.0242(11) 0.0342(12) -0.0052(10) 0.0059(10) -0.0038(9) C11 0.0337(12) 0.0273(12) 0.0256(11) -0.0046(9) 0.0005(10) -0.0042(9) C12 0.0265(11) 0.0269(11) 0.0280(11) -0.0045(9) 0.0031(10) -0.0010(9) C13 0.0523(16) 0.0286(13) 0.0291(12) -0.0013(10) -0.0030(12) 0.0079(12) C14 0.0590(17) 0.0324(13) 0.0293(12) -0.0065(11) -0.0004(13) 0.0056(12) C15 0.0362(13) 0.0246(12) 0.0425(14) -0.0079(11) 0.0079(11) 0.0023(10) C16 0.0364(14) 0.0343(13) 0.0397(14) -0.0042(11) -0.0063(11) 0.0100(11) C17 0.0338(13) 0.0367(13) 0.0325(12) -0.0067(11) -0.0043(11) 0.0052(11) C18 0.0273(12) 0.0309(12) 0.0367(13) -0.0039(10) -0.0023(10) -0.0061(9) C19 0.0400(14) 0.0278(12) 0.0282(12) -0.0013(10) -0.0023(10) -0.0071(10) C20 0.0448(18) 0.0363(16) 0.109(3) -0.0175(18) 0.0229(19) -0.0089(13) C21 0.062(2) 0.0417(18) 0.123(3) -0.014(2) 0.043(2) -0.0022(16) C22 0.080(2) 0.0315(14) 0.0472(16) -0.0083(13) 0.0170(16) -0.0022(14) C23 0.072(3) 0.0340(17) 0.105(3) -0.0210(18) -0.026(2) -0.0110(16) C24 0.0381(16) 0.0408(17) 0.105(3) -0.0140(18) -0.0198(18) -0.0007(14) _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 C15 1.741(2) . ? O1 C11 1.366(3) . ? O1 C1 1.449(3) . ? O2 C2 1.212(3) . ? O3 C11 1.195(3) . ? N1 C2 1.367(3) . ? N1 C3 1.420(3) . ? N1 C18 1.454(3) . ? C1 C4 1.497(3) . ? C1 C2 1.546(3) . ? C1 C9 1.548(3) . ? C3 C8 1.376(3) . ? C3 C4 1.389(3) . ? C4 C5 1.382(3) . ? C5 C6 1.398(4) . ? C5 H5A 0.9500 . ? C6 C7 1.376(4) . ? C6 H6A 0.9500 . ? C7 C8 1.388(4) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C12 1.505(3) . ? C9 C10 1.526(3) . ? C9 H9A 1.0000 . ? C10 C11 1.500(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C12 C17 1.387(3) . ? C12 C13 1.390(3) . ? C13 C14 1.382(3) . ? C13 H13A 0.9500 . ? C14 C15 1.381(4) . ? C14 H14A 0.9500 . ? C15 C16 1.382(4) . ? C16 C17 1.387(3) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.512(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.362(4) . ? C19 C20 1.395(4) . ? C20 C21 1.385(4) . ? C20 H20A 0.9500 . ? C21 C22 1.382(5) . ? C21 H21A 0.9500 . ? C22 C23 1.345(5) . ? C22 H22A 0.9500 . ? C23 C24 1.391(4) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? 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 O1 C1 110.78(17) . . ? C2 N1 C3 110.78(18) . . ? C2 N1 C18 123.7(2) . . ? C3 N1 C18 125.3(2) . . ? O1 C1 C4 111.83(18) . . ? O1 C1 C2 108.54(18) . . ? C4 C1 C2 102.47(18) . . ? O1 C1 C9 104.11(17) . . ? C4 C1 C9 116.3(2) . . ? C2 C1 C9 113.56(18) . . ? O2 C2 N1 126.5(2) . . ? O2 C2 C1 125.9(2) . . ? N1 C2 C1 107.66(18) . . ? C8 C3 C4 122.1(2) . . ? C8 C3 N1 128.3(2) . . ? C4 C3 N1 109.62(19) . . ? C5 C4 C3 120.3(2) . . ? C5 C4 C1 130.8(2) . . ? C3 C4 C1 108.93(19) . . ? C4 C5 C6 118.0(2) . . ? C4 C5 H5A 121.0 . . ? C6 C5 H5A 121.0 . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C6 C7 C8 121.5(2) . . ? C6 C7 H7A 119.2 . . ? C8 C7 H7A 119.2 . . ? C3 C8 C7 117.3(2) . . ? C3 C8 H8A 121.3 . . ? C7 C8 H8A 121.3 . . ? C12 C9 C10 117.9(2) . . ? C12 C9 C1 115.10(19) . . ? C10 C9 C1 101.85(19) . . ? C12 C9 H9A 107.1 . . ? C10 C9 H9A 107.1 . . ? C1 C9 H9A 107.1 . . ? C11 C10 C9 103.86(19) . . ? C11 C10 H10A 111.0 . . ? C9 C10 H10A 111.0 . . ? C11 C10 H10B 111.0 . . ? C9 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? O3 C11 O1 120.6(2) . . ? O3 C11 C10 129.8(2) . . ? O1 C11 C10 109.59(19) . . ? C17 C12 C13 118.3(2) . . ? C17 C12 C9 119.1(2) . . ? C13 C12 C9 122.5(2) . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C15 C14 C13 119.0(2) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? C14 C15 C16 121.4(2) . . ? C14 C15 Cl1 119.0(2) . . ? C16 C15 Cl1 119.5(2) . . ? C15 C16 C17 118.5(2) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? C16 C17 C12 121.5(2) . . ? C16 C17 H17A 119.3 . . ? C12 C17 H17A 119.3 . . ? N1 C18 C19 114.2(2) . . ? N1 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? N1 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C24 C19 C20 116.7(3) . . ? C24 C19 C18 120.2(2) . . ? C20 C19 C18 123.1(2) . . ? C21 C20 C19 120.8(3) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C22 C21 C20 120.5(4) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? C23 C22 C21 118.9(3) . . ? C23 C22 H22A 120.6 . . ? C21 C22 H22A 120.6 . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C19 C24 C23 122.4(3) . . ? C19 C24 H24A 118.8 . . ? C23 C24 H24A 118.8 . . ? 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 C11 O1 C1 C4 -148.69(19) . . . . ? C11 O1 C1 C2 99.0(2) . . . . ? C11 O1 C1 C9 -22.3(2) . . . . ? C3 N1 C2 O2 172.7(2) . . . . ? C18 N1 C2 O2 -2.7(4) . . . . ? C3 N1 C2 C1 -6.9(2) . . . . ? C18 N1 C2 C1 177.7(2) . . . . ? O1 C1 C2 O2 -53.9(3) . . . . ? C4 C1 C2 O2 -172.3(2) . . . . ? C9 C1 C2 O2 61.3(3) . . . . ? O1 C1 C2 N1 125.71(19) . . . . ? C4 C1 C2 N1 7.3(2) . . . . ? C9 C1 C2 N1 -119.0(2) . . . . ? C2 N1 C3 C8 -174.8(2) . . . . ? C18 N1 C3 C8 0.6(4) . . . . ? C2 N1 C3 C4 3.6(3) . . . . ? C18 N1 C3 C4 178.9(2) . . . . ? C8 C3 C4 C5 0.3(4) . . . . ? N1 C3 C4 C5 -178.2(2) . . . . ? C8 C3 C4 C1 179.9(2) . . . . ? N1 C3 C4 C1 1.5(3) . . . . ? O1 C1 C4 C5 58.3(3) . . . . ? C2 C1 C4 C5 174.4(3) . . . . ? C9 C1 C4 C5 -61.1(3) . . . . ? O1 C1 C4 C3 -121.3(2) . . . . ? C2 C1 C4 C3 -5.2(2) . . . . ? C9 C1 C4 C3 119.3(2) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C1 C4 C5 C6 -179.0(3) . . . . ? C4 C5 C6 C7 -0.9(5) . . . . ? C5 C6 C7 C8 0.6(5) . . . . ? C4 C3 C8 C7 -0.7(4) . . . . ? N1 C3 C8 C7 177.5(3) . . . . ? C6 C7 C8 C3 0.2(4) . . . . ? O1 C1 C9 C12 159.29(19) . . . . ? C4 C1 C9 C12 -77.2(3) . . . . ? C2 C1 C9 C12 41.4(3) . . . . ? O1 C1 C9 C10 30.5(2) . . . . ? C4 C1 C9 C10 154.05(19) . . . . ? C2 C1 C9 C10 -87.3(2) . . . . ? C12 C9 C10 C11 -154.9(2) . . . . ? C1 C9 C10 C11 -27.9(2) . . . . ? C1 O1 C11 O3 -176.1(2) . . . . ? C1 O1 C11 C10 4.1(3) . . . . ? C9 C10 C11 O3 -163.8(3) . . . . ? C9 C10 C11 O1 16.1(3) . . . . ? C10 C9 C12 C17 -151.9(2) . . . . ? C1 C9 C12 C17 87.8(3) . . . . ? C10 C9 C12 C13 29.0(3) . . . . ? C1 C9 C12 C13 -91.3(3) . . . . ? C17 C12 C13 C14 1.6(4) . . . . ? C9 C12 C13 C14 -179.3(2) . . . . ? C12 C13 C14 C15 -1.1(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C13 C14 C15 Cl1 179.4(2) . . . . ? C14 C15 C16 C17 1.7(4) . . . . ? Cl1 C15 C16 C17 -178.4(2) . . . . ? C15 C16 C17 C12 -1.1(4) . . . . ? C13 C12 C17 C16 -0.6(4) . . . . ? C9 C12 C17 C16 -179.7(2) . . . . ? C2 N1 C18 C19 -105.0(3) . . . . ? C3 N1 C18 C19 80.3(3) . . . . ? N1 C18 C19 C24 -177.1(3) . . . . ? N1 C18 C19 C20 1.5(4) . . . . ? C24 C19 C20 C21 -2.3(6) . . . . ? C18 C19 C20 C21 179.1(3) . . . . ? C19 C20 C21 C22 -0.1(6) . . . . ? C20 C21 C22 C23 2.9(6) . . . . ? C21 C22 C23 C24 -3.1(6) . . . . ? C20 C19 C24 C23 2.0(6) . . . . ? C18 C19 C24 C23 -179.3(3) . . . . ? C22 C23 C24 C19 0.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.453 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.047