# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_wanglong1008 _database_code_depnum_ccdc_archive 'CCDC 906655' #TrackingRef 'wanglong1008.cif' _audit_creation_date 2012-10-11 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H21 Cl N2 O5' _chemical_formula_sum 'C23 H21 Cl N2 O5' _chemical_formula_weight 440.87 _chemical_absolute_configuration ad _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 6.39013(18) _cell_length_b 16.4094(5) _cell_length_c 20.8853(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2190.00(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2790 _cell_measurement_temperature 292.19(10) _cell_measurement_theta_max 28.5678 _cell_measurement_theta_min 3.1512 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.99589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear dark colourless' _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_unetI/netI 0.0668 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 11081 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 28.63 _diffrn_reflns_theta_min 3.16 _diffrn_ambient_temperature 292.19(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9969 _diffrn_measured_fraction_theta_max 0.9691 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -20.00 25.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -19.1930 -99.0000 -30.0000 45 #__ type_ start__ end____ width___ exp.time_ 2 omega -48.00 29.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -57.0000 30.0000 77 #__ type_ start__ end____ width___ exp.time_ 3 omega 80.00 105.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -178.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega 42.00 67.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -99.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega -8.00 96.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 38.0000 -180.0000 104 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0256213000 _diffrn_orient_matrix_UB_12 -0.0248234000 _diffrn_orient_matrix_UB_13 0.0266664000 _diffrn_orient_matrix_UB_21 0.0192680000 _diffrn_orient_matrix_UB_22 0.0353826000 _diffrn_orient_matrix_UB_23 0.0186093000 _diffrn_orient_matrix_UB_31 -0.1062674000 _diffrn_orient_matrix_UB_32 0.0004150000 _diffrn_orient_matrix_UB_33 0.0098028000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3172 _reflns_number_total 4150 _reflns_odcompleteness_completeness 99.69 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.414 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(11) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 4150 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0563 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.2127P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1358 _refine_ls_wR_factor_ref 0.1508 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.70474(18) 0.07856(6) 0.42850(5) 0.0553(3) Uani 1 1 d . . . O1 O 0.2603(4) 0.44154(17) 0.37980(12) 0.0472(7) Uani 1 1 d . . . O2 O 0.4383(5) 0.6049(2) 0.54261(13) 0.0626(9) Uani 1 1 d . . . O3 O 0.7503(5) 0.6627(2) 0.54808(14) 0.0688(9) Uani 1 1 d U . . O4 O 0.4050(5) 0.65032(19) 0.32427(14) 0.0637(9) Uani 1 1 d . . . O5 O 0.6640(5) 0.71095(18) 0.37709(13) 0.0633(9) Uani 1 1 d . . . N1 N 0.4161(5) 0.4410(2) 0.28114(14) 0.0433(8) Uani 1 1 d . . . H1 H 0.3224 0.4143 0.2603 0.052 Uiso 1 1 calc R . . N2 N 0.7055(5) 0.48120(18) 0.47748(12) 0.0357(7) Uani 1 1 d . . . H2 H 0.6870 0.4567 0.5135 0.043 Uiso 1 1 calc R . . C2 C 0.5998(6) 0.4736(2) 0.25344(17) 0.0419(9) Uani 1 1 d . . . C3 C 0.6587(8) 0.4763(3) 0.19006(18) 0.0586(12) Uani 1 1 d . . . H3 H 0.5748 0.4535 0.1584 0.070 Uiso 1 1 calc R . . C4 C 0.8450(8) 0.5137(3) 0.17480(19) 0.0586(12) Uani 1 1 d . . . H4 H 0.8863 0.5167 0.1322 0.070 Uiso 1 1 calc R . . C5 C 0.9714(7) 0.5467(3) 0.22145(18) 0.0533(11) Uani 1 1 d . . . H5 H 1.0984 0.5705 0.2103 0.064 Uiso 1 1 calc R . . C6 C 0.9098(6) 0.5447(2) 0.28452(17) 0.0403(9) Uani 1 1 d . . . H6 H 0.9947 0.5673 0.3160 0.048 Uiso 1 1 calc R . . C7 C 0.7216(5) 0.5088(2) 0.30115(14) 0.0322(8) Uani 1 1 d . . . C8 C 0.6121(5) 0.4972(2) 0.36461(15) 0.0296(7) Uani 1 1 d . . . C9 C 0.4063(6) 0.4567(2) 0.34408(17) 0.0372(8) Uani 1 1 d . . . C10 C 0.5628(5) 0.5742(2) 0.40532(14) 0.0314(7) Uani 1 1 d . . . H10 H 0.4202 0.5660 0.4213 0.038 Uiso 1 1 calc R . . C11 C 0.7045(5) 0.5690(2) 0.46467(15) 0.0318(7) Uani 1 1 d . . . C12 C 0.7454(5) 0.4449(2) 0.41449(14) 0.0312(7) Uani 1 1 d . . . H12 H 0.8929 0.4557 0.4047 0.037 Uiso 1 1 calc R . . C13 C 0.9285(6) 0.6030(3) 0.46139(18) 0.0440(9) Uani 1 1 d U . . H13A H 1.0301 0.5597 0.4671 0.053 Uiso 1 1 calc R . . H13B H 0.9534 0.6290 0.4204 0.053 Uiso 1 1 calc R . . C14 C 0.9442(9) 0.6619(5) 0.5130(3) 0.102(2) Uani 1 1 d U . . H14A H 1.0586 0.6474 0.5413 0.122 Uiso 1 1 calc R . . H14B H 0.9720 0.7157 0.4956 0.122 Uiso 1 1 calc R . . C15 C 0.6132(6) 0.6129(2) 0.52124(17) 0.0413(9) Uani 1 1 d . . . C16 C 0.5559(6) 0.6526(2) 0.36833(16) 0.0406(9) Uani 1 1 d . . . C17 C 0.3880(9) 0.7205(3) 0.2804(3) 0.0818(17) Uani 1 1 d . . . H17A H 0.2468 0.7232 0.2635 0.098 Uiso 1 1 calc R . . H17B H 0.4142 0.7704 0.3041 0.098 Uiso 1 1 calc R . . C18 C 0.5303(14) 0.7151(4) 0.2293(3) 0.122(3) Uani 1 1 d . . . H18A H 0.5115 0.7608 0.2012 0.184 Uiso 1 1 calc R . . H18B H 0.5060 0.6655 0.2061 0.184 Uiso 1 1 calc R . . H18C H 0.6706 0.7152 0.2457 0.184 Uiso 1 1 calc R . . C19 C 0.7206(5) 0.3531(2) 0.41420(13) 0.0291(7) Uani 1 1 d . . . C20 C 0.8792(5) 0.3054(2) 0.38882(17) 0.0378(8) Uani 1 1 d . . . H20 H 0.9913 0.3308 0.3686 0.045 Uiso 1 1 calc R . . C21 C 0.8761(5) 0.2218(2) 0.39252(18) 0.0397(9) Uani 1 1 d . . . H21 H 0.9862 0.1910 0.3763 0.048 Uiso 1 1 calc R . . C22 C 0.7060(6) 0.1846(2) 0.42081(15) 0.0388(8) Uani 1 1 d . . . C23 C 0.5448(6) 0.2285(2) 0.44533(16) 0.0404(9) Uani 1 1 d . . . H23 H 0.4312 0.2023 0.4640 0.048 Uiso 1 1 calc R . . C24 C 0.5511(6) 0.3138(2) 0.44222(16) 0.0384(9) Uani 1 1 d . . . H24 H 0.4412 0.3442 0.4590 0.046 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 0.0719(7) 0.0297(5) 0.0643(6) -0.0004(5) 0.0050(5) -0.0057(5) O1 0.0316(13) 0.0520(17) 0.0581(16) 0.0045(13) -0.0001(12) -0.0071(13) O2 0.0635(19) 0.071(2) 0.0535(17) -0.0159(15) 0.0173(16) 0.0023(17) O3 0.073(2) 0.074(2) 0.0591(16) -0.0303(16) 0.0002(15) -0.0084(18) O4 0.0658(18) 0.0489(18) 0.0763(19) 0.0191(16) -0.0369(16) -0.0038(16) O5 0.094(2) 0.0366(16) 0.0597(18) 0.0070(13) -0.0233(17) -0.0146(18) N1 0.0436(17) 0.046(2) 0.0399(16) -0.0101(15) -0.0118(14) -0.0078(16) N2 0.0497(16) 0.0323(16) 0.0252(13) 0.0047(12) -0.0037(13) 0.0005(15) C2 0.047(2) 0.042(2) 0.0367(18) 0.0003(17) 0.0002(17) 0.006(2) C3 0.082(3) 0.058(3) 0.035(2) -0.006(2) -0.004(2) 0.011(3) C4 0.075(3) 0.062(3) 0.038(2) 0.002(2) 0.015(2) 0.005(3) C5 0.049(2) 0.061(3) 0.050(2) 0.011(2) 0.0165(19) 0.005(2) C6 0.0385(19) 0.046(2) 0.0365(18) 0.0068(17) 0.0063(16) 0.0006(19) C7 0.0351(17) 0.0328(19) 0.0286(16) 0.0039(14) 0.0011(14) 0.0046(17) C8 0.0254(15) 0.0309(19) 0.0324(16) 0.0024(14) -0.0020(13) -0.0015(15) C9 0.0336(18) 0.033(2) 0.045(2) 0.0075(16) -0.0062(17) 0.0012(17) C10 0.0304(16) 0.0334(19) 0.0305(16) 0.0028(15) 0.0018(13) -0.0011(16) C11 0.0332(17) 0.0281(18) 0.0342(17) 0.0002(14) -0.0003(14) 0.0017(17) C12 0.0313(17) 0.0307(19) 0.0315(16) 0.0000(13) -0.0010(13) 0.0023(15) C13 0.0400(19) 0.043(2) 0.049(2) 0.0011(17) -0.0090(17) -0.0057(18) C14 0.076(3) 0.125(4) 0.104(4) -0.048(3) 0.013(3) -0.033(3) C15 0.052(2) 0.038(2) 0.0338(18) -0.0021(16) -0.0056(18) 0.002(2) C16 0.050(2) 0.035(2) 0.0375(19) 0.0003(16) 0.0006(17) 0.002(2) C17 0.103(4) 0.053(3) 0.090(4) 0.025(3) -0.045(3) 0.000(3) C18 0.221(9) 0.087(5) 0.059(3) 0.020(3) -0.044(5) 0.011(5) C19 0.0287(16) 0.0320(19) 0.0264(15) 0.0037(13) 0.0025(13) -0.0024(16) C20 0.0302(17) 0.040(2) 0.044(2) 0.0017(17) 0.0023(15) -0.0038(18) C21 0.0389(19) 0.030(2) 0.050(2) -0.0076(17) 0.0083(17) 0.0028(18) C22 0.053(2) 0.0256(18) 0.0379(18) 0.0017(15) -0.0037(18) -0.0037(18) C23 0.0365(19) 0.043(2) 0.0419(19) 0.0040(17) 0.0120(15) -0.0031(19) C24 0.0390(19) 0.036(2) 0.0407(19) 0.0001(16) 0.0063(16) 0.0033(18) _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 C22 1.747(4) . ? O1 C9 1.220(4) . ? O2 C15 1.211(5) . ? O3 C14 1.439(6) . ? O3 C15 1.322(5) . ? O4 C16 1.333(4) . ? O4 C17 1.476(5) . ? O5 C16 1.195(4) . ? N1 H1 0.8600 . ? N1 C2 1.414(5) . ? N1 C9 1.341(5) . ? N2 H2 0.8600 . ? N2 C11 1.466(4) . ? N2 C12 1.467(4) . ? C2 C3 1.377(5) . ? C2 C7 1.391(5) . ? C3 H3 0.9300 . ? C3 C4 1.376(6) . ? C4 H4 0.9300 . ? C4 C5 1.376(6) . ? C5 H5 0.9300 . ? C5 C6 1.375(5) . ? C6 H6 0.9300 . ? C6 C7 1.383(5) . ? C7 C8 1.511(4) . ? C8 C9 1.534(5) . ? C8 C10 1.554(5) . ? C8 C12 1.597(4) . ? C10 H10 0.9800 . ? C10 C11 1.537(4) . ? C10 C16 1.502(5) . ? C11 C13 1.538(5) . ? C11 C15 1.502(5) . ? C12 H12 0.9800 . ? C12 C19 1.514(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.452(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.404(9) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.385(5) . ? C19 C24 1.391(5) . ? C20 H20 0.9300 . ? C20 C21 1.375(5) . ? C21 H21 0.9300 . ? C21 C22 1.379(5) . ? C22 C23 1.358(5) . ? C23 H23 0.9300 . ? C23 C24 1.401(5) . ? C24 H24 0.9300 . ? 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 C15 O3 C14 110.5(3) . . ? C16 O4 C17 117.4(3) . . ? C2 N1 H1 124.2 . . ? C9 N1 H1 124.2 . . ? C9 N1 C2 111.5(3) . . ? C11 N2 H2 128.2 . . ? C11 N2 C12 103.7(2) . . ? C12 N2 H2 128.2 . . ? C3 C2 N1 129.3(4) . . ? C3 C2 C7 121.5(4) . . ? C7 C2 N1 109.2(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 C2 118.3(4) . . ? C4 C3 H3 120.9 . . ? C3 C4 H4 119.4 . . ? C3 C4 C5 121.3(4) . . ? C5 C4 H4 119.4 . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C5 C6 H6 120.0 . . ? C5 C6 C7 120.0(4) . . ? C7 C6 H6 120.0 . . ? C2 C7 C8 108.5(3) . . ? C6 C7 C2 118.9(3) . . ? C6 C7 C8 132.6(3) . . ? C7 C8 C9 101.9(3) . . ? C7 C8 C10 118.1(3) . . ? C7 C8 C12 113.1(3) . . ? C9 C8 C10 109.3(3) . . ? C9 C8 C12 114.0(3) . . ? C10 C8 C12 100.9(2) . . ? O1 C9 N1 126.5(3) . . ? O1 C9 C8 125.0(3) . . ? N1 C9 C8 108.5(3) . . ? C8 C10 H10 105.4 . . ? C11 C10 C8 106.1(3) . . ? C11 C10 H10 105.4 . . ? C16 C10 C8 114.9(3) . . ? C16 C10 H10 105.4 . . ? C16 C10 C11 118.6(3) . . ? N2 C11 C10 101.7(3) . . ? N2 C11 C13 111.1(3) . . ? N2 C11 C15 109.3(3) . . ? C10 C11 C13 119.5(3) . . ? C15 C11 C10 112.3(3) . . ? C15 C11 C13 102.9(3) . . ? N2 C12 C8 105.9(3) . . ? N2 C12 H12 106.3 . . ? N2 C12 C19 112.9(3) . . ? C8 C12 H12 106.3 . . ? C19 C12 C8 118.5(3) . . ? C19 C12 H12 106.3 . . ? C11 C13 H13A 110.6 . . ? C11 C13 H13B 110.6 . . ? H13A C13 H13B 108.7 . . ? C14 C13 C11 105.8(4) . . ? C14 C13 H13A 110.6 . . ? C14 C13 H13B 110.6 . . ? O3 C14 C13 108.9(4) . . ? O3 C14 H14A 109.9 . . ? O3 C14 H14B 109.9 . . ? C13 C14 H14A 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O2 C15 O3 121.5(4) . . ? O2 C15 C11 126.6(4) . . ? O3 C15 C11 111.9(3) . . ? O4 C16 C10 110.6(3) . . ? O5 C16 O4 123.1(4) . . ? O5 C16 C10 126.2(3) . . ? O4 C17 H17A 109.2 . . ? O4 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C18 C17 O4 112.0(5) . . ? C18 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C12 119.1(3) . . ? C20 C19 C24 117.9(3) . . ? C24 C19 C12 122.8(3) . . ? C19 C20 H20 118.9 . . ? C21 C20 C19 122.1(3) . . ? C21 C20 H20 118.9 . . ? C20 C21 H21 120.7 . . ? C20 C21 C22 118.5(3) . . ? C22 C21 H21 120.7 . . ? C21 C22 Cl1 119.0(3) . . ? C23 C22 Cl1 119.4(3) . . ? C23 C22 C21 121.6(3) . . ? C22 C23 H23 120.3 . . ? C22 C23 C24 119.4(3) . . ? C24 C23 H23 120.3 . . ? C19 C24 C23 120.4(3) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? 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 Cl1 C22 C23 C24 176.6(3) . . . . ? N1 C2 C3 C4 178.3(4) . . . . ? N1 C2 C7 C6 180.0(3) . . . . ? N1 C2 C7 C8 1.0(4) . . . . ? N2 C11 C13 C14 -118.0(4) . . . . ? N2 C11 C15 O2 -61.0(5) . . . . ? N2 C11 C15 O3 117.4(4) . . . . ? N2 C12 C19 C20 -129.4(3) . . . . ? N2 C12 C19 C24 46.2(4) . . . . ? C2 N1 C9 O1 174.4(4) . . . . ? C2 N1 C9 C8 -5.9(4) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C2 C7 C8 C9 -4.2(4) . . . . ? C2 C7 C8 C10 -123.9(3) . . . . ? C2 C7 C8 C12 118.6(3) . . . . ? C3 C2 C7 C6 -2.5(6) . . . . ? C3 C2 C7 C8 178.6(4) . . . . ? C3 C4 C5 C6 -1.7(7) . . . . ? C4 C5 C6 C7 0.5(6) . . . . ? C5 C6 C7 C2 1.5(5) . . . . ? C5 C6 C7 C8 -179.8(4) . . . . ? C6 C7 C8 C9 177.1(4) . . . . ? C6 C7 C8 C10 57.3(5) . . . . ? C6 C7 C8 C12 -60.1(5) . . . . ? C7 C2 C3 C4 1.3(7) . . . . ? C7 C8 C9 O1 -174.2(3) . . . . ? C7 C8 C9 N1 6.1(4) . . . . ? C7 C8 C10 C11 -111.5(3) . . . . ? C7 C8 C10 C16 21.6(4) . . . . ? C7 C8 C12 N2 143.2(3) . . . . ? C7 C8 C12 C19 -88.8(3) . . . . ? C8 C10 C11 N2 -36.5(3) . . . . ? C8 C10 C11 C13 86.2(4) . . . . ? C8 C10 C11 C15 -153.2(3) . . . . ? C8 C10 C16 O4 61.8(4) . . . . ? C8 C10 C16 O5 -120.3(4) . . . . ? C8 C12 C19 C20 106.1(3) . . . . ? C8 C12 C19 C24 -78.3(4) . . . . ? C9 N1 C2 C3 -174.1(4) . . . . ? C9 N1 C2 C7 3.2(5) . . . . ? C9 C8 C10 C11 132.7(3) . . . . ? C9 C8 C10 C16 -94.2(3) . . . . ? C9 C8 C12 N2 -100.9(3) . . . . ? C9 C8 C12 C19 27.0(4) . . . . ? C10 C8 C9 O1 -48.4(5) . . . . ? C10 C8 C9 N1 131.9(3) . . . . ? C10 C8 C12 N2 16.1(3) . . . . ? C10 C8 C12 C19 144.1(3) . . . . ? C10 C11 C13 C14 124.1(4) . . . . ? C10 C11 C15 O2 51.1(5) . . . . ? C10 C11 C15 O3 -130.4(3) . . . . ? C11 N2 C12 C8 -40.0(3) . . . . ? C11 N2 C12 C19 -171.2(3) . . . . ? C11 C10 C16 O4 -171.3(3) . . . . ? C11 C10 C16 O5 6.7(6) . . . . ? C11 C13 C14 O3 2.5(6) . . . . ? C12 N2 C11 C10 47.2(3) . . . . ? C12 N2 C11 C13 -81.1(3) . . . . ? C12 N2 C11 C15 166.1(3) . . . . ? C12 C8 C9 O1 63.5(5) . . . . ? C12 C8 C9 N1 -116.1(3) . . . . ? C12 C8 C10 C11 12.3(3) . . . . ? C12 C8 C10 C16 145.4(3) . . . . ? C12 C19 C20 C21 173.7(3) . . . . ? C12 C19 C24 C23 -174.6(3) . . . . ? C13 C11 C15 O2 -179.2(4) . . . . ? C13 C11 C15 O3 -0.7(4) . . . . ? C14 O3 C15 O2 -179.1(5) . . . . ? C14 O3 C15 C11 2.3(6) . . . . ? C15 O3 C14 C13 -3.1(7) . . . . ? C15 C11 C13 C14 -1.2(5) . . . . ? C16 O4 C17 C18 82.0(6) . . . . ? C16 C10 C11 N2 -167.5(3) . . . . ? C16 C10 C11 C13 -44.8(5) . . . . ? C16 C10 C11 C15 75.8(4) . . . . ? C17 O4 C16 O5 6.5(6) . . . . ? C17 O4 C16 C10 -175.4(4) . . . . ? C19 C20 C21 C22 2.0(5) . . . . ? C20 C19 C24 C23 1.1(5) . . . . ? C20 C21 C22 Cl1 -177.6(3) . . . . ? C20 C21 C22 C23 -0.7(5) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C19 0.1(5) . . . . ? C24 C19 C20 C21 -2.2(5) . . . . ? _smtbx_masks_special_details ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.032 0.333 0.205 32.5 6.2 ? 2 -0.032 0.833 0.295 32.5 6.1 ? 3 0.468 0.667 0.705 32.5 6.2 ? 4 0.532 0.167 0.795 32.5 6.2 ?