# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_120530_s2_oyl _database_code_depnum_ccdc_archive 'CCDC 889672' #TrackingRef '12360_web_deposit_cif_file_0_BoHan_1341281341.120530_s2_oyl.cif' _audit_creation_date 2012-05-30 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H21 Cl N2 O5' _chemical_formula_sum 'C26 H21 Cl N2 O5' _chemical_formula_weight 476.90 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C20H22N2O1Cl1 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' _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 8.7125(6) _cell_length_b 11.9908(6) _cell_length_c 22.8948(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2391.8(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2118 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1145 _cell_measurement_theta_min 2.8840 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0899 _diffrn_reflns_av_unetI/netI 0.0940 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 10633 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.89 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -43.00 48.00 0.7000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 77.0000 120.0000 130 #__ type_ start__ end____ width___ exp.time_ 2 omega -9.00 19.00 0.7000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 77.0000 -120.0000 40 #__ type_ start__ end____ width___ exp.time_ 3 omega 65.00 90.20 0.7000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 77.0000 -120.0000 36 #__ type_ start__ end____ width___ exp.time_ 4 omega -10.00 83.10 0.7000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 77.0000 0.0000 133 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0479723000 _diffrn_orient_matrix_UB_12 0.0010546000 _diffrn_orient_matrix_UB_13 -0.0250010000 _diffrn_orient_matrix_UB_21 -0.0080001000 _diffrn_orient_matrix_UB_22 -0.0588466000 _diffrn_orient_matrix_UB_23 0.0014896000 _diffrn_orient_matrix_UB_31 -0.0653434000 _diffrn_orient_matrix_UB_32 0.0063603000 _diffrn_orient_matrix_UB_33 0.0181662000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2912 _reflns_number_total 4879 _reflns_odcompleteness_completeness 99.72 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _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, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.321 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(12) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 308 _refine_ls_number_reflns 4879 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0697 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1537 _refine_ls_wR_factor_ref 0.1862 _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 -0.47471(17) -0.06189(10) -0.22812(6) 0.0842(4) Uani 1 1 d . . . O1 O -0.1809(3) -0.3171(2) -0.05768(11) 0.0587(7) Uani 1 1 d . . . O2 O -0.0464(4) -0.3043(3) 0.02191(13) 0.0771(9) Uani 1 1 d . . . O3 O -0.0599(4) -0.5341(2) -0.08695(14) 0.0694(8) Uani 1 1 d . . . O4 O -0.4179(4) -0.6035(2) -0.12319(14) 0.0758(9) Uani 1 1 d . . . O5 O -0.6125(4) -0.4941(3) -0.12147(18) 0.1001(12) Uani 1 1 d . . . N1 N -0.1255(4) -0.4690(3) -0.17820(15) 0.0589(9) Uani 1 1 d . . . N2 N -0.4821(4) -0.5181(3) -0.10824(15) 0.0573(8) Uani 1 1 d . . . C1 C -0.3824(5) -0.1898(4) -0.21759(18) 0.0610(11) Uani 1 1 d . . . C2 C -0.3773(5) -0.2324(3) -0.16202(18) 0.0578(10) Uani 1 1 d . . . H2 H -0.4285 -0.1980 -0.1313 0.069 Uiso 1 1 calc R . . C3 C -0.2929(5) -0.3287(3) -0.15363(16) 0.0529(10) Uani 1 1 d . . . C4 C -0.2144(5) -0.3788(3) -0.19966(17) 0.0544(10) Uani 1 1 d . . . C5 C -0.2267(6) -0.3382(4) -0.25550(18) 0.0669(13) Uani 1 1 d . . . H5 H -0.1806 -0.3745 -0.2868 0.080 Uiso 1 1 calc R . . C6 C -0.3106(6) -0.2410(4) -0.2635(2) 0.0722(13) Uani 1 1 d . . . H6 H -0.3182 -0.2101 -0.3007 0.087 Uiso 1 1 calc R . . C7 C -0.2569(5) -0.3909(3) -0.09837(17) 0.0525(10) Uani 1 1 d . . . C8 C -0.1356(5) -0.4759(3) -0.11910(18) 0.0546(10) Uani 1 1 d . . . C9 C -0.3981(4) -0.4409(3) -0.06763(15) 0.0478(9) Uani 1 1 d . . . H9 H -0.4673 -0.3799 -0.0567 0.057 Uiso 1 1 calc R . . C10 C -0.3548(5) -0.5049(3) -0.01252(15) 0.0507(10) Uani 1 1 d . . . H10 H -0.2908 -0.5686 -0.0237 0.061 Uiso 1 1 calc R . . C11 C -0.2601(5) -0.4283(3) 0.02756(17) 0.0562(10) Uani 1 1 d . . . H11 H -0.3345 -0.3804 0.0476 0.067 Uiso 1 1 calc R . . C12 C -0.1504(5) -0.3512(3) -0.00240(16) 0.0543(10) Uani 1 1 d . . . C13 C -0.4955(5) -0.5485(3) 0.01905(17) 0.0525(10) Uani 1 1 d . . . C14 C -0.6142(5) -0.4805(4) 0.0346(2) 0.0678(12) Uani 1 1 d . . . H14 H -0.6109 -0.4055 0.0243 0.081 Uiso 1 1 calc R . . C15 C -0.7391(6) -0.5201(4) 0.0653(2) 0.0837(15) Uani 1 1 d . . . H15 H -0.8184 -0.4719 0.0754 0.100 Uiso 1 1 calc R . . C16 C -0.7470(7) -0.6294(5) 0.0810(3) 0.0946(17) Uani 1 1 d . . . H16 H -0.8300 -0.6561 0.1023 0.114 Uiso 1 1 calc R . . C17 C -0.6305(7) -0.6989(4) 0.0649(3) 0.0925(18) Uani 1 1 d . . . H17 H -0.6351 -0.7740 0.0750 0.111 Uiso 1 1 calc R . . C18 C -0.5070(6) -0.6599(3) 0.0341(2) 0.0727(13) Uani 1 1 d . . . H18 H -0.4297 -0.7091 0.0232 0.087 Uiso 1 1 calc R . . C19 C -0.1811(6) -0.4949(5) 0.0751(2) 0.0916(17) Uani 1 1 d . . . H19A H -0.2553 -0.5406 0.0949 0.137 Uiso 1 1 calc R . . H19B H -0.1345 -0.4448 0.1026 0.137 Uiso 1 1 calc R . . H19C H -0.1036 -0.5415 0.0580 0.137 Uiso 1 1 calc R . . C20 C -0.0100(5) -0.5287(4) -0.2121(2) 0.0730(13) Uani 1 1 d . . . H20A H 0.0619 -0.5634 -0.1853 0.088 Uiso 1 1 calc R . . H20B H 0.0467 -0.4753 -0.2354 0.088 Uiso 1 1 calc R . . C21 C -0.0742(5) -0.6173(4) -0.25195(19) 0.0621(11) Uani 1 1 d . . . C22 C -0.0209(7) -0.6224(5) -0.3085(2) 0.0824(16) Uani 1 1 d . . . H22 H 0.0493 -0.5702 -0.3223 0.099 Uiso 1 1 calc R . . C23 C -0.0738(10) -0.7064(7) -0.3444(3) 0.118(3) Uani 1 1 d . . . H23 H -0.0366 -0.7116 -0.3824 0.141 Uiso 1 1 calc R . . C24 C -0.1774(9) -0.7804(6) -0.3258(4) 0.119(3) Uani 1 1 d . . . H24 H -0.2124 -0.8355 -0.3510 0.142 Uiso 1 1 calc R . . C25 C -0.2325(7) -0.7758(5) -0.2699(4) 0.106(2) Uani 1 1 d . . . H25 H -0.3052 -0.8270 -0.2571 0.127 Uiso 1 1 calc R . . C26 C -0.1772(6) -0.6924(4) -0.2324(3) 0.0802(14) Uani 1 1 d . . . H26 H -0.2116 -0.6890 -0.1939 0.096 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 0.1052(10) 0.0659(7) 0.0815(8) 0.0198(7) -0.0107(7) 0.0047(7) O1 0.0776(19) 0.0389(14) 0.0595(15) -0.0019(14) -0.0039(15) -0.0131(14) O2 0.087(2) 0.0643(18) 0.0801(19) -0.0013(17) -0.0196(18) -0.0208(19) O3 0.0651(19) 0.0566(18) 0.086(2) 0.0052(17) -0.0003(16) 0.0049(16) O4 0.085(2) 0.0541(17) 0.089(2) -0.0237(17) -0.0049(18) 0.0010(18) O5 0.066(2) 0.110(3) 0.125(3) -0.031(2) -0.032(2) 0.013(2) N1 0.057(2) 0.0522(19) 0.067(2) -0.0105(18) 0.0103(17) -0.0042(18) N2 0.061(2) 0.0497(19) 0.0610(19) -0.0057(18) 0.0002(18) -0.0060(18) C1 0.074(3) 0.053(2) 0.055(2) 0.006(2) -0.005(2) -0.009(2) C2 0.063(3) 0.051(2) 0.060(3) 0.002(2) 0.004(2) -0.004(2) C3 0.060(2) 0.043(2) 0.056(2) -0.003(2) 0.0011(19) -0.007(2) C4 0.062(3) 0.045(2) 0.056(2) -0.0100(19) 0.0085(19) -0.010(2) C5 0.079(3) 0.066(3) 0.055(2) -0.014(2) 0.009(2) -0.018(3) C6 0.089(3) 0.073(3) 0.055(2) 0.011(2) -0.001(3) -0.013(3) C7 0.061(2) 0.039(2) 0.057(2) -0.0033(19) 0.002(2) -0.003(2) C8 0.056(2) 0.043(2) 0.065(3) -0.001(2) 0.001(2) -0.008(2) C9 0.051(2) 0.0397(19) 0.053(2) -0.0058(18) 0.0017(17) -0.0025(18) C10 0.057(2) 0.040(2) 0.055(2) -0.0009(19) -0.0014(18) 0.0009(17) C11 0.061(3) 0.054(2) 0.055(2) 0.001(2) -0.0035(19) -0.009(2) C12 0.068(3) 0.042(2) 0.054(2) -0.004(2) -0.007(2) -0.006(2) C13 0.063(3) 0.037(2) 0.058(2) -0.0011(18) -0.0003(19) 0.0032(19) C14 0.073(3) 0.039(2) 0.091(3) 0.007(2) 0.013(3) -0.005(2) C15 0.074(3) 0.064(3) 0.113(4) 0.008(3) 0.021(3) -0.008(3) C16 0.096(4) 0.073(4) 0.115(4) 0.015(3) 0.029(4) -0.015(3) C17 0.107(4) 0.048(3) 0.123(5) 0.019(3) 0.007(4) -0.020(3) C18 0.081(3) 0.041(2) 0.097(3) 0.006(2) 0.011(3) -0.004(2) C19 0.086(4) 0.095(4) 0.093(3) 0.028(3) -0.027(3) -0.024(3) C20 0.064(3) 0.065(3) 0.090(3) -0.017(3) 0.020(2) -0.004(2) C21 0.063(3) 0.051(2) 0.072(3) -0.006(2) 0.009(2) 0.015(2) C22 0.106(4) 0.075(3) 0.066(3) -0.001(3) 0.013(3) 0.029(3) C23 0.155(7) 0.121(5) 0.077(3) -0.030(4) -0.036(4) 0.075(5) C24 0.111(6) 0.085(5) 0.160(8) -0.058(5) -0.067(6) 0.047(4) C25 0.074(4) 0.061(3) 0.182(7) -0.033(4) -0.006(4) 0.004(3) C26 0.074(3) 0.063(3) 0.103(3) -0.019(3) 0.017(3) -0.001(3) _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 C1 1.749(5) . ? O1 C7 1.446(5) . ? O1 C12 1.356(4) . ? O2 C12 1.203(5) . ? O3 C8 1.210(5) . ? O4 N2 1.216(4) . ? O5 N2 1.211(4) . ? N1 C4 1.418(5) . ? N1 C8 1.359(5) . ? N1 C20 1.458(5) . ? N2 C9 1.502(5) . ? C1 C2 1.372(6) . ? C1 C6 1.368(6) . ? C2 H2 0.9300 . ? C2 C3 1.383(6) . ? C3 C4 1.393(6) . ? C3 C7 1.502(5) . ? C4 C5 1.372(6) . ? C5 H5 0.9300 . ? C5 C6 1.389(7) . ? C6 H6 0.9300 . ? C7 C8 1.543(5) . ? C7 C9 1.538(5) . ? C9 H9 0.9800 . ? C9 C10 1.524(5) . ? C10 H10 0.9800 . ? C10 C11 1.539(5) . ? C10 C13 1.516(5) . ? C11 H11 0.9800 . ? C11 C12 1.496(5) . ? C11 C19 1.515(6) . ? C13 C14 1.365(5) . ? C13 C18 1.384(5) . ? C14 H14 0.9300 . ? C14 C15 1.380(6) . ? C15 H15 0.9300 . ? C15 C16 1.360(7) . ? C16 H16 0.9300 . ? C16 C17 1.364(8) . ? C17 H17 0.9300 . ? C17 C18 1.368(7) . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C21 1.508(6) . ? C21 C22 1.378(6) . ? C21 C26 1.348(6) . ? C22 H22 0.9300 . ? C22 C23 1.379(8) . ? C23 H23 0.9300 . ? C23 C24 1.335(11) . ? C24 H24 0.9300 . ? C24 C25 1.367(10) . ? C25 H25 0.9300 . ? C25 C26 1.404(8) . ? C26 H26 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 C12 O1 C7 120.5(3) . . ? C4 N1 C20 124.6(4) . . ? C8 N1 C4 110.9(3) . . ? C8 N1 C20 123.0(4) . . ? O4 N2 C9 118.0(3) . . ? O5 N2 O4 124.1(4) . . ? O5 N2 C9 117.8(4) . . ? C2 C1 Cl1 118.0(3) . . ? C6 C1 Cl1 119.8(3) . . ? C6 C1 C2 122.1(4) . . ? C1 C2 H2 121.4 . . ? C1 C2 C3 117.2(4) . . ? C3 C2 H2 121.4 . . ? C2 C3 C4 121.1(4) . . ? C2 C3 C7 130.0(4) . . ? C4 C3 C7 108.7(4) . . ? C3 C4 N1 109.6(3) . . ? C5 C4 N1 129.5(4) . . ? C5 C4 C3 120.9(4) . . ? C4 C5 H5 121.2 . . ? C4 C5 C6 117.5(4) . . ? C6 C5 H5 121.2 . . ? C1 C6 C5 121.0(4) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O1 C7 C3 109.5(3) . . ? O1 C7 C8 106.8(3) . . ? O1 C7 C9 108.1(3) . . ? C3 C7 C8 102.2(3) . . ? C3 C7 C9 114.3(3) . . ? C9 C7 C8 115.5(3) . . ? O3 C8 N1 127.3(4) . . ? O3 C8 C7 124.6(4) . . ? N1 C8 C7 108.1(4) . . ? N2 C9 C7 110.3(3) . . ? N2 C9 H9 108.5 . . ? N2 C9 C10 108.8(3) . . ? C7 C9 H9 108.5 . . ? C10 C9 C7 112.2(3) . . ? C10 C9 H9 108.5 . . ? C9 C10 H10 108.4 . . ? C9 C10 C11 109.0(3) . . ? C11 C10 H10 108.4 . . ? C13 C10 C9 111.6(3) . . ? C13 C10 H10 108.4 . . ? C13 C10 C11 110.8(3) . . ? C10 C11 H11 105.9 . . ? C12 C11 C10 116.0(3) . . ? C12 C11 H11 105.9 . . ? C12 C11 C19 111.4(4) . . ? C19 C11 C10 110.9(3) . . ? C19 C11 H11 105.9 . . ? O1 C12 C11 119.3(4) . . ? O2 C12 O1 116.0(4) . . ? O2 C12 C11 123.9(4) . . ? C14 C13 C10 122.1(3) . . ? C14 C13 C18 117.2(4) . . ? C18 C13 C10 120.7(4) . . ? C13 C14 H14 119.2 . . ? C13 C14 C15 121.7(4) . . ? C15 C14 H14 119.2 . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.4(5) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 120.7 . . ? C15 C16 C17 118.7(5) . . ? C17 C16 H16 120.7 . . ? C16 C17 H17 119.5 . . ? C16 C17 C18 121.0(4) . . ? C18 C17 H17 119.5 . . ? C13 C18 H18 119.5 . . ? C17 C18 C13 121.0(5) . . ? C17 C18 H18 119.5 . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 H20A 108.7 . . ? N1 C20 H20B 108.7 . . ? N1 C20 C21 114.3(3) . . ? H20A C20 H20B 107.6 . . ? C21 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C22 C21 C20 118.4(5) . . ? C26 C21 C20 121.0(4) . . ? C26 C21 C22 120.5(5) . . ? C21 C22 H22 120.6 . . ? C21 C22 C23 118.7(6) . . ? C23 C22 H22 120.6 . . ? C22 C23 H23 119.3 . . ? C24 C23 C22 121.4(7) . . ? C24 C23 H23 119.3 . . ? C23 C24 H24 119.7 . . ? C23 C24 C25 120.6(6) . . ? C25 C24 H24 119.7 . . ? C24 C25 H25 120.6 . . ? C24 C25 C26 118.8(6) . . ? C26 C25 H25 120.6 . . ? C21 C26 C25 120.0(6) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? data_120530_s3_oyl _database_code_depnum_ccdc_archive 'CCDC 889673' #TrackingRef '12361_web_deposit_cif_file_1_BoHan_1341281341.120530_s3_oyl.cif' _audit_creation_date 2012-05-30 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H21 Cl N2 O5' _chemical_formula_sum 'C26 H21 Cl N2 O5' _chemical_formula_weight 476.90 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C20H22N2O1Cl1 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' _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 6.9973(3) _cell_length_b 16.3475(6) _cell_length_c 19.9730(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2284.68(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1805 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.9498 _cell_measurement_theta_min 3.0535 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_unetI/netI 0.0582 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 6181 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.08 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -1.00 36.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 77.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega -20.00 22.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -101.0000 -170.0000 42 #__ type_ start__ end____ width___ exp.time_ 3 omega 35.00 95.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 178.0000 120.0000 60 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0236472000 _diffrn_orient_matrix_UB_12 -0.0198106000 _diffrn_orient_matrix_UB_13 -0.0304891000 _diffrn_orient_matrix_UB_21 -0.0438336000 _diffrn_orient_matrix_UB_22 -0.0364068000 _diffrn_orient_matrix_UB_23 0.0116923000 _diffrn_orient_matrix_UB_31 -0.0883367000 _diffrn_orient_matrix_UB_32 0.0128049000 _diffrn_orient_matrix_UB_33 -0.0139392000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2767 _reflns_number_total 3910 _reflns_odcompleteness_completeness 99.71 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _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, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.181 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(8) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 308 _refine_ls_number_reflns 3910 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0485 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.0830 _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 -0.13861(12) -0.21378(5) -0.06656(4) 0.0666(3) Uani 1 1 d . . . O1 O -0.4125(2) -0.48314(11) 0.06707(9) 0.0434(5) Uani 1 1 d . . . O2 O -0.7009(3) -0.51885(17) 0.09560(11) 0.0813(8) Uani 1 1 d . . . O3 O -0.1599(4) -0.63474(11) 0.08216(10) 0.0678(7) Uani 1 1 d . . . O4 O 0.0717(4) -0.37233(17) 0.18076(15) 0.1049(10) Uani 1 1 d . . . O5 O -0.2118(4) -0.33252(13) 0.15575(12) 0.0731(7) Uani 1 1 d . . . N1 N -0.0107(4) -0.55742(14) 0.00169(11) 0.0442(6) Uani 1 1 d . . . N2 N -0.0910(5) -0.38485(18) 0.16280(12) 0.0547(7) Uani 1 1 d . . . C1 C -0.0809(4) -0.31402(17) -0.04595(14) 0.0449(7) Uani 1 1 d . . . C2 C -0.1649(4) -0.34848(16) 0.00995(13) 0.0428(7) Uani 1 1 d . . . H2 H -0.2457 -0.3180 0.0373 0.051 Uiso 1 1 calc R . . C3 C -0.1255(4) -0.42944(16) 0.02417(12) 0.0377(6) Uani 1 1 d . . . C4 C -0.0109(4) -0.47445(18) -0.01827(13) 0.0400(7) Uani 1 1 d . . . C5 C 0.0754(4) -0.44006(19) -0.07310(13) 0.0488(8) Uani 1 1 d . . . H5 H 0.1553 -0.4707 -0.1006 0.059 Uiso 1 1 calc R . . C6 C 0.0396(4) -0.35784(19) -0.08615(15) 0.0497(8) Uani 1 1 d . . . H6 H 0.0981 -0.3325 -0.1225 0.060 Uiso 1 1 calc R . . C7 C -0.2093(4) -0.48544(16) 0.07632(13) 0.0386(7) Uani 1 1 d . . . C8 C -0.1266(4) -0.56987(17) 0.05494(14) 0.0457(7) Uani 1 1 d . . . C9 C -0.1462(4) -0.47283(15) 0.14985(11) 0.0365(6) Uani 1 1 d . . . H9 H -0.0330 -0.5068 0.1576 0.044 Uiso 1 1 calc R . . C10 C -0.2958(4) -0.49535(15) 0.20307(11) 0.0332(6) Uani 1 1 d . . . H10 H -0.3550 -0.4439 0.2173 0.040 Uiso 1 1 calc R . . C11 C -0.4584(4) -0.54949(16) 0.17645(13) 0.0399(7) Uani 1 1 d . . . H11 H -0.4067 -0.6043 0.1685 0.048 Uiso 1 1 calc R . . C12 C -0.5357(5) -0.5177(2) 0.11141(15) 0.0487(8) Uani 1 1 d . . . C13 C -0.2011(4) -0.53160(16) 0.26501(13) 0.0381(7) Uani 1 1 d . . . C14 C -0.1793(4) -0.4848(2) 0.32168(13) 0.0533(8) Uani 1 1 d . . . H14 H -0.2208 -0.4308 0.3218 0.064 Uiso 1 1 calc R . . C15 C -0.0960(5) -0.5174(3) 0.37871(17) 0.0771(12) Uani 1 1 d . . . H15 H -0.0814 -0.4853 0.4168 0.093 Uiso 1 1 calc R . . C16 C -0.0359(5) -0.5963(3) 0.3788(2) 0.0826(13) Uani 1 1 d . . . H16 H 0.0185 -0.6182 0.4173 0.099 Uiso 1 1 calc R . . C17 C -0.0543(5) -0.6442(2) 0.3228(2) 0.0773(12) Uani 1 1 d . . . H17 H -0.0121 -0.6981 0.3233 0.093 Uiso 1 1 calc R . . C18 C -0.1362(5) -0.61174(17) 0.26527(16) 0.0579(9) Uani 1 1 d . . . H18 H -0.1475 -0.6437 0.2270 0.069 Uiso 1 1 calc R . . C19 C -0.6181(4) -0.55668(17) 0.22800(13) 0.0531(8) Uani 1 1 d . . . H19A H -0.5684 -0.5803 0.2684 0.080 Uiso 1 1 calc R . . H19B H -0.7179 -0.5909 0.2106 0.080 Uiso 1 1 calc R . . H19C H -0.6687 -0.5033 0.2375 0.080 Uiso 1 1 calc R . . C20 C 0.1114(5) -0.62077(19) -0.02610(15) 0.0601(9) Uani 1 1 d . . . H20A H 0.1308 -0.6627 0.0076 0.072 Uiso 1 1 calc R . . H20B H 0.2351 -0.5971 -0.0363 0.072 Uiso 1 1 calc R . . C21 C 0.0342(5) -0.66049(18) -0.08842(16) 0.0565(9) Uani 1 1 d . . . C22 C 0.1353(7) -0.6578(2) -0.14841(18) 0.0819(12) Uani 1 1 d . . . H22 H 0.2537 -0.6320 -0.1504 0.098 Uiso 1 1 calc R . . C23 C 0.0573(8) -0.6941(2) -0.2059(2) 0.0936(16) Uani 1 1 d . . . H23 H 0.1223 -0.6913 -0.2464 0.112 Uiso 1 1 calc R . . C24 C -0.1102(10) -0.7328(2) -0.2022(2) 0.1066(19) Uani 1 1 d . . . H24 H -0.1590 -0.7576 -0.2405 0.128 Uiso 1 1 calc R . . C25 C -0.2128(8) -0.7371(2) -0.1436(2) 0.1035(16) Uani 1 1 d . . . H25 H -0.3295 -0.7643 -0.1419 0.124 Uiso 1 1 calc R . . C26 C -0.1386(6) -0.70014(19) -0.08739(18) 0.0760(11) Uani 1 1 d . . . H26 H -0.2075 -0.7021 -0.0476 0.091 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 0.0641(5) 0.0606(5) 0.0751(5) 0.0266(5) -0.0021(6) -0.0057(4) O1 0.0362(11) 0.0572(12) 0.0367(10) 0.0049(10) -0.0045(10) -0.0046(9) O2 0.0387(13) 0.143(2) 0.0622(14) 0.0218(16) -0.0136(13) -0.0180(15) O3 0.0989(18) 0.0424(11) 0.0621(13) 0.0059(11) 0.0210(16) 0.0056(13) O4 0.086(2) 0.104(2) 0.124(2) 0.0059(18) -0.028(2) -0.0554(17) O5 0.110(2) 0.0449(13) 0.0647(15) -0.0014(13) 0.0018(17) -0.0026(15) N1 0.0435(14) 0.0504(15) 0.0388(13) -0.0065(13) 0.0006(13) 0.0084(13) N2 0.066(2) 0.0629(19) 0.0350(14) 0.0049(15) -0.0038(16) -0.0256(17) C1 0.0384(17) 0.0523(17) 0.0439(16) 0.0099(15) -0.0075(16) -0.0085(15) C2 0.0417(18) 0.0495(16) 0.0372(15) 0.0018(14) 0.0001(16) -0.0010(15) C3 0.0365(16) 0.0459(15) 0.0307(13) -0.0001(14) -0.0047(15) -0.0017(15) C4 0.0353(15) 0.0517(18) 0.0330(14) 0.0023(15) -0.0059(15) 0.0004(15) C5 0.0408(17) 0.069(2) 0.0366(15) -0.0031(17) 0.0048(16) -0.0032(16) C6 0.0435(18) 0.067(2) 0.0387(16) 0.0112(17) 0.0019(17) -0.0090(17) C7 0.0362(16) 0.0451(15) 0.0346(15) 0.0017(15) 0.0013(15) 0.0002(13) C8 0.0491(18) 0.0496(17) 0.0385(15) -0.0017(15) -0.0023(18) 0.0041(17) C9 0.0358(15) 0.0405(15) 0.0332(13) 0.0044(13) -0.0005(15) -0.0025(14) C10 0.0326(15) 0.0353(14) 0.0317(13) 0.0016(13) 0.0011(14) 0.0025(13) C11 0.0377(16) 0.0438(16) 0.0382(15) 0.0058(14) 0.0000(15) -0.0028(14) C12 0.0432(18) 0.059(2) 0.0436(17) -0.0002(17) -0.0040(17) -0.0060(17) C13 0.0318(15) 0.0454(16) 0.0372(15) 0.0089(14) -0.0030(15) -0.0046(14) C14 0.0464(18) 0.072(2) 0.0411(15) 0.0039(17) -0.0001(17) -0.0064(18) C15 0.054(2) 0.134(4) 0.0435(18) 0.014(2) -0.010(2) -0.022(3) C16 0.039(2) 0.141(4) 0.068(3) 0.054(3) -0.006(2) -0.011(3) C17 0.050(2) 0.074(2) 0.108(3) 0.051(3) 0.002(3) 0.0087(19) C18 0.054(2) 0.0518(19) 0.068(2) 0.0161(17) 0.002(2) 0.0072(19) C19 0.0467(19) 0.0625(19) 0.0502(17) 0.0090(16) 0.0025(19) -0.0065(17) C20 0.059(2) 0.063(2) 0.0592(19) -0.0013(18) -0.001(2) 0.0178(19) C21 0.081(3) 0.0384(17) 0.050(2) 0.0009(16) 0.004(2) 0.0207(18) C22 0.111(3) 0.064(2) 0.070(2) 0.000(2) 0.023(3) 0.025(3) C23 0.166(5) 0.060(3) 0.055(2) -0.004(2) 0.028(3) 0.027(3) C24 0.214(6) 0.043(2) 0.063(3) -0.001(2) -0.024(4) 0.015(3) C25 0.167(5) 0.056(2) 0.087(3) 0.000(2) -0.013(4) -0.026(3) C26 0.116(3) 0.0508(19) 0.061(2) -0.0026(19) 0.002(3) -0.017(2) _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 C1 1.737(3) . ? O1 C7 1.435(3) . ? O1 C12 1.359(3) . ? O2 C12 1.199(3) . ? O3 C8 1.214(3) . ? O4 N2 1.211(3) . ? O5 N2 1.211(3) . ? N1 C4 1.414(3) . ? N1 C8 1.353(3) . ? N1 C20 1.453(3) . ? N2 C9 1.511(4) . ? C1 C2 1.382(3) . ? C1 C6 1.367(4) . ? C2 H2 0.9300 . ? C2 C3 1.381(3) . ? C3 C4 1.380(4) . ? C3 C7 1.506(3) . ? C4 C5 1.371(4) . ? C5 H5 0.9300 . ? C5 C6 1.392(4) . ? C6 H6 0.9300 . ? C7 C8 1.556(4) . ? C7 C9 1.547(3) . ? C9 H9 0.9800 . ? C9 C10 1.537(3) . ? C10 H10 0.9800 . ? C10 C11 1.536(3) . ? C10 C13 1.524(3) . ? C11 H11 0.9800 . ? C11 C12 1.500(4) . ? C11 C19 1.524(3) . ? C13 C14 1.374(4) . ? C13 C18 1.387(4) . ? C14 H14 0.9300 . ? C14 C15 1.386(4) . ? C15 H15 0.9300 . ? C15 C16 1.357(5) . ? C16 H16 0.9300 . ? C16 C17 1.371(5) . ? C17 H17 0.9300 . ? C17 C18 1.388(4) . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C21 1.504(4) . ? C21 C22 1.392(4) . ? C21 C26 1.372(5) . ? C22 H22 0.9300 . ? C22 C23 1.403(5) . ? C23 H23 0.9300 . ? C23 C24 1.333(6) . ? C24 H24 0.9300 . ? C24 C25 1.376(6) . ? C25 H25 0.9300 . ? C25 C26 1.376(5) . ? C26 H26 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 C12 O1 C7 122.3(2) . . ? C4 N1 C20 125.2(2) . . ? C8 N1 C4 111.4(2) . . ? C8 N1 C20 123.1(2) . . ? O4 N2 C9 116.9(3) . . ? O5 N2 O4 124.8(3) . . ? O5 N2 C9 118.3(3) . . ? C2 C1 Cl1 118.5(2) . . ? C6 C1 Cl1 119.9(2) . . ? C6 C1 C2 121.6(3) . . ? C1 C2 H2 120.9 . . ? C3 C2 C1 118.2(3) . . ? C3 C2 H2 120.9 . . ? C2 C3 C7 130.3(3) . . ? C4 C3 C2 120.0(2) . . ? C4 C3 C7 109.1(2) . . ? C3 C4 N1 109.8(2) . . ? C5 C4 N1 128.2(3) . . ? C5 C4 C3 121.9(3) . . ? C4 C5 H5 121.1 . . ? C4 C5 C6 117.8(3) . . ? C6 C5 H5 121.1 . . ? C1 C6 C5 120.5(3) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O1 C7 C3 106.3(2) . . ? O1 C7 C8 110.9(2) . . ? O1 C7 C9 113.7(2) . . ? C3 C7 C8 101.8(2) . . ? C3 C7 C9 117.7(2) . . ? C9 C7 C8 105.8(2) . . ? O3 C8 N1 126.7(3) . . ? O3 C8 C7 125.5(3) . . ? N1 C8 C7 107.8(2) . . ? N2 C9 C7 111.2(2) . . ? N2 C9 H9 107.8 . . ? N2 C9 C10 106.5(2) . . ? C7 C9 H9 107.8 . . ? C10 C9 C7 115.5(2) . . ? C10 C9 H9 107.8 . . ? C9 C10 H10 106.4 . . ? C11 C10 C9 113.77(19) . . ? C11 C10 H10 106.4 . . ? C13 C10 C9 111.00(19) . . ? C13 C10 H10 106.4 . . ? C13 C10 C11 112.3(2) . . ? C10 C11 H11 108.0 . . ? C12 C11 C10 111.5(2) . . ? C12 C11 H11 108.0 . . ? C12 C11 C19 110.3(2) . . ? C19 C11 C10 110.7(2) . . ? C19 C11 H11 108.0 . . ? O1 C12 C11 118.7(2) . . ? O2 C12 O1 116.5(3) . . ? O2 C12 C11 124.8(3) . . ? C14 C13 C10 120.0(2) . . ? C14 C13 C18 119.1(3) . . ? C18 C13 C10 120.9(3) . . ? C13 C14 H14 119.7 . . ? C13 C14 C15 120.6(3) . . ? C15 C14 H14 119.7 . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.8(4) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.6 . . ? C15 C16 C17 120.8(4) . . ? C17 C16 H16 119.6 . . ? C16 C17 H17 120.1 . . ? C16 C17 C18 119.7(3) . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 119.9(3) . . ? C13 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 H20A 108.7 . . ? N1 C20 H20B 108.7 . . ? N1 C20 C21 114.4(3) . . ? H20A C20 H20B 107.6 . . ? C21 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C22 C21 C20 121.1(3) . . ? C26 C21 C20 120.5(3) . . ? C26 C21 C22 118.4(3) . . ? C21 C22 H22 120.2 . . ? C21 C22 C23 119.5(4) . . ? C23 C22 H22 120.2 . . ? C22 C23 H23 120.1 . . ? C24 C23 C22 119.9(5) . . ? C24 C23 H23 120.1 . . ? C23 C24 H24 119.0 . . ? C23 C24 C25 122.0(5) . . ? C25 C24 H24 119.0 . . ? C24 C25 H25 120.8 . . ? C26 C25 C24 118.4(5) . . ? C26 C25 H25 120.8 . . ? C21 C26 C25 121.9(4) . . ? C21 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ?