# 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_zhangjl0510 _audit_creation_date 2013-05-10 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H22 N4 O6' _chemical_formula_sum 'C22 H22 N4 O6' _chemical_formula_weight 438.44 _chemical_absolute_configuration unk _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' _space_group_crystal_system hexagonal _space_group_IT_number 170 _space_group_name_H-M_alt 'P 65' _space_group_name_Hall 'P 65' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x-y, x, z+5/6' 3 '-y, x-y, z+2/3' 4 '-x, -y, z+1/2' 5 '-x+y, -x, z+1/3' 6 'y, -x+y, z+1/6' _cell_length_a 19.4670(10) _cell_length_b 19.4670(10) _cell_length_c 10.8548(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3562.5(3) _cell_formula_units_Z 6 _cell_measurement_reflns_used 2275 _cell_measurement_temperature 296.24(10) _cell_measurement_theta_max 20.8630 _cell_measurement_theta_min 3.6910 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1380 _exptl_crystal_size_max 0.3300 _exptl_crystal_size_mid 0.2200 _exptl_crystal_size_min 0.1800 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_unetI/netI 0.0677 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8537 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.67 _diffrn_reflns_theta_min 3.06 _diffrn_ambient_temperature 296.24(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9977 _diffrn_measured_fraction_theta_max 0.7908 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -25.00 42.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -57.0000 120.0000 67 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 56.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 19.0000 0.0000 78 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0212528000 _diffrn_orient_matrix_UB_12 -0.0228668000 _diffrn_orient_matrix_UB_13 0.0518798000 _diffrn_orient_matrix_UB_21 -0.0192098000 _diffrn_orient_matrix_UB_22 0.0226956000 _diffrn_orient_matrix_UB_23 0.0055380000 _diffrn_orient_matrix_UB_31 -0.0307888000 _diffrn_orient_matrix_UB_32 -0.0270304000 _diffrn_orient_matrix_UB_33 -0.0393573000 _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 2620 _reflns_number_total 4102 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.763 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.074 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(3) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 293 _refine_ls_number_reflns 4102 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.1251 _refine_ls_R_factor_gt 0.0869 _refine_ls_restrained_S_all 1.104 _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^)+(0.1520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2303 _refine_ls_wR_factor_ref 0.2721 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(O2) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 3.a Ternary CH refined with riding coordinates: C7(H7), C8(H8) 3.b Secondary CH2 refined with riding coordinates: C12(H12A,H12B) 3.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10) 3.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B, H22C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 O1 O -0.5487(3) -0.5758(3) -0.3331(4) 0.0793(13) Uani 1 1 d . . . O2 O -0.5907(3) -0.8471(3) -0.7602(5) 0.0812(14) Uani 1 1 d U . . O3 O -0.7529(4) -0.7995(5) -0.6050(9) 0.143(3) Uani 1 1 d U . . O4 O -0.8356(5) -0.9138(6) -0.6695(15) 0.205(5) Uani 1 1 d U . . O5 O -0.6878(2) -0.6088(3) -0.6464(4) 0.0697(12) Uani 1 1 d . . . O6 O -0.6881(2) -0.6163(3) -0.4389(4) 0.0724(12) Uani 1 1 d . . . N1 N -0.3479(4) -0.5900(3) -1.2520(5) 0.0777(16) Uani 1 1 d . . . N2 N -0.6455(6) -0.9214(4) -0.8102(8) 0.105(2) Uani 1 1 d U . . N3 N -0.7679(4) -0.8593(5) -0.6582(9) 0.112(2) Uani 1 1 d U . . N4 N -0.5817(3) -0.5981(3) -0.5417(4) 0.0512(11) Uani 1 1 d . . . C1 C -0.5427(3) -0.6276(3) -0.9489(5) 0.0500(12) Uani 1 1 d . . . H1 H -0.5842 -0.6169 -0.9457 0.060 Uiso 1 1 calc R . . C2 C -0.5004(3) -0.6114(3) -1.0531(5) 0.0544(13) Uani 1 1 d . . . H2 H -0.5134 -0.5909 -1.1208 0.065 Uiso 1 1 calc R . . C3 C -0.4369(3) -0.6253(3) -1.0596(5) 0.0498(12) Uani 1 1 d . . . C4 C -0.4196(3) -0.6581(3) -0.9588(6) 0.0598(14) Uani 1 1 d . . . H4 H -0.3779 -0.6685 -0.9627 0.072 Uiso 1 1 calc R . . C5 C -0.4647(3) -0.6751(3) -0.8527(5) 0.0555(13) Uani 1 1 d . . . H5 H -0.4528 -0.6971 -0.7857 0.067 Uiso 1 1 calc R . . C6 C -0.5270(3) -0.6603(3) -0.8437(5) 0.0427(11) Uani 1 1 d . . . C7 C -0.5746(3) -0.6721(3) -0.7273(4) 0.0454(11) Uani 1 1 d . . . H7 H -0.6280 -0.6852 -0.7527 0.055 Uiso 1 1 calc R . . C8 C -0.5383(3) -0.5927(3) -0.6549(5) 0.0508(13) Uani 1 1 d . . . H8 H -0.5379 -0.5519 -0.7082 0.061 Uiso 1 1 calc R . . C9 C -0.4563(4) -0.5645(4) -0.6097(7) 0.0683(16) Uani 1 1 d . . . H9 H -0.4132 -0.5532 -0.6597 0.082 Uiso 1 1 calc R . . C10 C -0.4535(4) -0.5575(4) -0.4866(7) 0.0711(17) Uani 1 1 d . . . H10 H -0.4083 -0.5418 -0.4391 0.085 Uiso 1 1 calc R . . C11 C -0.5311(3) -0.5779(3) -0.4374(6) 0.0582(14) Uani 1 1 d . . . C12 C -0.5834(4) -0.7395(3) -0.6436(5) 0.0560(14) Uani 1 1 d . . . H12A H -0.5311 -0.7307 -0.6231 0.067 Uiso 1 1 calc R . . H12B H -0.6090 -0.7385 -0.5675 0.067 Uiso 1 1 calc R . . C13 C -0.6296(4) -0.8176(3) -0.7005(5) 0.0582(14) Uani 1 1 d U . . C14 C -0.7082(5) -0.8693(4) -0.7097(7) 0.0757(18) Uani 1 1 d U . . C15 C -0.7157(6) -0.9356(4) -0.7843(9) 0.094(2) Uani 1 1 d U . . C16 C -0.7871(8) -1.0112(7) -0.8228(16) 0.164(5) Uani 1 1 d U . . H16A H -0.7845 -1.0189 -0.9097 0.245 Uiso 1 1 calc R . . H16B H -0.8340 -1.0087 -0.8047 0.245 Uiso 1 1 calc R . . H16C H -0.7885 -1.0547 -0.7789 0.245 Uiso 1 1 calc R . . C17 C -0.3888(4) -0.6055(3) -1.1675(6) 0.0625(15) Uani 1 1 d . . . C18 C -0.6576(3) -0.6082(3) -0.5490(5) 0.0518(12) Uani 1 1 d . . . C19 C -0.7670(4) -0.6221(4) -0.4188(6) 0.0709(17) Uani 1 1 d . . . C20 C -0.8297(5) -0.6965(6) -0.4831(12) 0.122(3) Uani 1 1 d . . . H20A H -0.8119 -0.6991 -0.5645 0.183 Uiso 1 1 calc R . . H20B H -0.8783 -0.6951 -0.4883 0.183 Uiso 1 1 calc R . . H20C H -0.8387 -0.7424 -0.4370 0.183 Uiso 1 1 calc R . . C21 C -0.7660(5) -0.5490(5) -0.4675(9) 0.090(2) Uani 1 1 d . . . H21A H -0.7238 -0.5028 -0.4289 0.134 Uiso 1 1 calc R . . H21B H -0.8157 -0.5521 -0.4496 0.134 Uiso 1 1 calc R . . H21C H -0.7577 -0.5457 -0.5550 0.134 Uiso 1 1 calc R . . C22 C -0.7746(7) -0.6256(7) -0.2808(10) 0.134(4) Uani 1 1 d . . . H22A H -0.7559 -0.6592 -0.2484 0.201 Uiso 1 1 calc R . . H22B H -0.8293 -0.6468 -0.2585 0.201 Uiso 1 1 calc R . . H22C H -0.7436 -0.5732 -0.2473 0.201 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 O1 0.096(3) 0.104(3) 0.040(3) -0.011(2) -0.009(2) 0.051(3) O2 0.112(3) 0.067(3) 0.080(3) 0.003(2) 0.014(3) 0.056(3) O3 0.111(5) 0.115(5) 0.211(9) -0.031(5) 0.030(5) 0.063(4) O4 0.098(5) 0.173(7) 0.312(13) -0.017(8) -0.004(7) 0.043(6) O5 0.075(3) 0.104(3) 0.047(3) -0.002(2) -0.004(2) 0.057(3) O6 0.074(3) 0.110(3) 0.041(2) 0.009(2) 0.012(2) 0.052(3) N1 0.086(4) 0.068(3) 0.071(4) 0.004(3) 0.029(3) 0.032(3) N2 0.149(6) 0.067(4) 0.100(5) -0.005(3) 0.013(4) 0.054(4) N3 0.074(4) 0.099(5) 0.151(6) 0.005(4) 0.007(4) 0.036(4) N4 0.060(3) 0.060(3) 0.035(2) -0.0016(19) -0.0003(19) 0.031(2) C1 0.055(3) 0.054(3) 0.051(3) 0.005(2) 0.002(2) 0.035(2) C2 0.068(3) 0.063(3) 0.041(3) 0.006(2) 0.005(2) 0.039(3) C3 0.057(3) 0.049(3) 0.043(3) -0.005(2) 0.006(2) 0.026(2) C4 0.046(3) 0.070(4) 0.070(4) -0.004(3) 0.004(3) 0.033(3) C5 0.066(3) 0.073(4) 0.043(3) 0.007(3) 0.002(2) 0.046(3) C6 0.053(3) 0.040(2) 0.039(3) 0.0010(19) 0.004(2) 0.025(2) C7 0.052(3) 0.049(3) 0.038(3) 0.002(2) 0.005(2) 0.027(2) C8 0.060(3) 0.049(3) 0.041(3) -0.001(2) 0.010(2) 0.025(2) C9 0.057(3) 0.069(4) 0.067(4) -0.011(3) 0.005(3) 0.023(3) C10 0.059(4) 0.078(4) 0.072(5) -0.018(3) -0.018(3) 0.031(3) C11 0.064(4) 0.062(3) 0.049(4) -0.007(3) -0.011(3) 0.031(3) C12 0.069(4) 0.057(3) 0.041(3) 0.003(2) 0.001(2) 0.031(3) C13 0.077(4) 0.057(3) 0.050(3) 0.013(3) 0.007(3) 0.042(3) C14 0.092(4) 0.058(3) 0.082(4) 0.001(3) 0.001(4) 0.042(3) C15 0.118(6) 0.056(4) 0.091(5) -0.007(3) -0.021(5) 0.032(4) C16 0.180(11) 0.102(7) 0.161(10) -0.028(7) -0.021(9) 0.034(7) C17 0.074(4) 0.054(3) 0.059(4) -0.003(3) 0.015(3) 0.031(3) C18 0.060(3) 0.060(3) 0.039(3) 0.005(2) 0.003(3) 0.033(3) C19 0.067(4) 0.084(4) 0.060(4) 0.001(3) 0.015(3) 0.037(3) C20 0.088(6) 0.101(6) 0.150(9) -0.016(6) 0.013(6) 0.026(5) C21 0.106(6) 0.098(5) 0.094(6) 0.003(4) 0.022(4) 0.073(5) C22 0.146(9) 0.208(11) 0.078(6) 0.035(7) 0.061(6) 0.111(9) _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 O1 C11 1.189(7) . ? O2 N2 1.407(9) . ? O2 C13 1.325(7) . ? O3 N3 1.198(10) . ? O4 N3 1.217(10) . ? O5 C18 1.207(7) . ? O6 C18 1.308(7) . ? O6 C19 1.499(7) . ? N1 C17 1.150(8) . ? N2 C15 1.281(11) . ? N3 C14 1.388(10) . ? N4 C8 1.465(7) . ? N4 C11 1.421(7) . ? N4 C18 1.392(7) . ? C1 H1 0.9300 . ? C1 C2 1.340(8) . ? C1 C6 1.413(7) . ? C2 H2 0.9300 . ? C2 C3 1.393(7) . ? C3 C4 1.390(8) . ? C3 C17 1.428(8) . ? C4 H4 0.9300 . ? C4 C5 1.385(9) . ? C5 H5 0.9300 . ? C5 C6 1.383(7) . ? C6 C7 1.514(7) . ? C7 H7 0.9800 . ? C7 C8 1.554(7) . ? C7 C12 1.533(7) . ? C8 H8 0.9800 . ? C8 C9 1.487(9) . ? C9 H9 0.9300 . ? C9 C10 1.342(10) . ? C10 H10 0.9300 . ? C10 C11 1.458(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.462(8) . ? C13 C14 1.351(9) . ? C14 C15 1.469(11) . ? C15 C16 1.492(13) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C19 C20 1.520(11) . ? C19 C21 1.508(10) . ? C19 C22 1.504(12) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C13 O2 N2 109.3(6) . . ? C18 O6 C19 121.8(5) . . ? C15 N2 O2 108.4(6) . . ? O3 N3 O4 121.8(10) . . ? O3 N3 C14 121.1(7) . . ? O4 N3 C14 117.1(10) . . ? C11 N4 C8 110.7(4) . . ? C18 N4 C8 119.8(4) . . ? C18 N4 C11 128.6(5) . . ? C2 C1 H1 118.6 . . ? C2 C1 C6 122.8(5) . . ? C6 C1 H1 118.6 . . ? C1 C2 H2 120.1 . . ? C1 C2 C3 119.8(5) . . ? C3 C2 H2 120.1 . . ? C2 C3 C17 121.0(5) . . ? C4 C3 C2 119.5(5) . . ? C4 C3 C17 119.5(5) . . ? C3 C4 H4 120.2 . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4 120.2 . . ? C4 C5 H5 119.1 . . ? C6 C5 C4 121.7(5) . . ? C6 C5 H5 119.1 . . ? C1 C6 C7 119.3(4) . . ? C5 C6 C1 116.5(5) . . ? C5 C6 C7 124.1(5) . . ? C6 C7 H7 107.2 . . ? C6 C7 C8 109.4(4) . . ? C6 C7 C12 115.1(4) . . ? C8 C7 H7 107.2 . . ? C12 C7 H7 107.2 . . ? C12 C7 C8 110.6(4) . . ? N4 C8 C7 113.2(4) . . ? N4 C8 H8 108.8 . . ? N4 C8 C9 103.0(5) . . ? C7 C8 H8 108.8 . . ? C9 C8 C7 113.9(4) . . ? C9 C8 H8 108.8 . . ? C8 C9 H9 124.8 . . ? C10 C9 C8 110.3(6) . . ? C10 C9 H9 124.8 . . ? C9 C10 H10 124.7 . . ? C9 C10 C11 110.7(5) . . ? C11 C10 H10 124.7 . . ? O1 C11 N4 126.6(6) . . ? O1 C11 C10 128.0(6) . . ? N4 C11 C10 105.3(5) . . ? C7 C12 H12A 109.0 . . ? C7 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C13 C12 C7 112.8(5) . . ? C13 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? O2 C13 C12 118.0(6) . . ? O2 C13 C14 108.8(6) . . ? C14 C13 C12 133.2(6) . . ? N3 C14 C15 128.6(8) . . ? C13 C14 N3 125.6(7) . . ? C13 C14 C15 105.8(7) . . ? N2 C15 C14 107.8(7) . . ? N2 C15 C16 121.2(9) . . ? C14 C15 C16 130.9(10) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 C3 177.5(7) . . ? O5 C18 O6 127.6(5) . . ? O5 C18 N4 121.9(5) . . ? O6 C18 N4 110.5(5) . . ? O6 C19 C20 108.0(6) . . ? O6 C19 C21 110.4(5) . . ? O6 C19 C22 102.8(6) . . ? C21 C19 C20 111.3(7) . . ? C22 C19 C20 113.5(8) . . ? C22 C19 C21 110.3(7) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 O2 N2 C15 C14 -1.9(9) . . . . ? O2 N2 C15 C16 -178.7(10) . . . . ? O2 C13 C14 N3 179.5(7) . . . . ? O2 C13 C14 C15 -0.7(7) . . . . ? O3 N3 C14 C13 4.1(15) . . . . ? O3 N3 C14 C15 -175.7(9) . . . . ? O4 N3 C14 C13 -175.9(10) . . . . ? O4 N3 C14 C15 4.3(16) . . . . ? N2 O2 C13 C12 -178.7(5) . . . . ? N2 O2 C13 C14 -0.4(7) . . . . ? N3 C14 C15 N2 -178.5(8) . . . . ? N3 C14 C15 C16 -2.2(17) . . . . ? N4 C8 C9 C10 2.2(7) . . . . ? C1 C2 C3 C4 1.8(8) . . . . ? C1 C2 C3 C17 -177.4(5) . . . . ? C1 C6 C7 C8 -82.5(6) . . . . ? C1 C6 C7 C12 152.4(5) . . . . ? C2 C1 C6 C5 0.0(8) . . . . ? C2 C1 C6 C7 176.3(5) . . . . ? C2 C3 C4 C5 -1.2(8) . . . . ? C2 C3 C17 N1 166(14) . . . . ? C3 C4 C5 C6 -0.1(9) . . . . ? C4 C3 C17 N1 -13(15) . . . . ? C4 C5 C6 C1 0.7(8) . . . . ? C4 C5 C6 C7 -175.5(5) . . . . ? C5 C6 C7 C8 93.5(6) . . . . ? C5 C6 C7 C12 -31.6(7) . . . . ? C6 C1 C2 C3 -1.3(8) . . . . ? C6 C7 C8 N4 178.7(4) . . . . ? C6 C7 C8 C9 -64.1(6) . . . . ? C6 C7 C12 C13 -65.5(7) . . . . ? C7 C8 C9 C10 -120.8(6) . . . . ? C7 C12 C13 O2 93.8(6) . . . . ? C7 C12 C13 C14 -83.9(8) . . . . ? C8 N4 C11 O1 179.1(6) . . . . ? C8 N4 C11 C10 1.4(6) . . . . ? C8 N4 C18 O5 -3.7(8) . . . . ? C8 N4 C18 O6 176.2(4) . . . . ? C8 C7 C12 C13 170.0(5) . . . . ? C8 C9 C10 C11 -1.5(8) . . . . ? C9 C10 C11 O1 -177.6(7) . . . . ? C9 C10 C11 N4 0.1(7) . . . . ? C11 N4 C8 C7 121.3(5) . . . . ? C11 N4 C8 C9 -2.1(6) . . . . ? C11 N4 C18 O5 164.0(5) . . . . ? C11 N4 C18 O6 -16.0(8) . . . . ? C12 C7 C8 N4 -53.6(6) . . . . ? C12 C7 C8 C9 63.6(6) . . . . ? C12 C13 C14 N3 -2.7(13) . . . . ? C12 C13 C14 C15 177.2(6) . . . . ? C13 O2 N2 C15 1.6(9) . . . . ? C13 C14 C15 N2 1.7(9) . . . . ? C13 C14 C15 C16 178.0(11) . . . . ? C17 C3 C4 C5 178.1(5) . . . . ? C18 O6 C19 C20 62.9(8) . . . . ? C18 O6 C19 C21 -59.1(8) . . . . ? C18 O6 C19 C22 -176.7(7) . . . . ? C18 N4 C8 C7 -68.9(6) . . . . ? C18 N4 C8 C9 167.7(5) . . . . ? C18 N4 C11 O1 10.5(10) . . . . ? C18 N4 C11 C10 -167.3(5) . . . . ? C19 O6 C18 O5 -4.6(9) . . . . ? C19 O6 C18 N4 175.4(5) . . . . ? _platon_squeeze_details ; ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.017 296 26 ' ' _database_code_depnum_ccdc_archive 'CCDC 941171' ####################################################################### # # 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_zhangjl0524 _audit_creation_date 2013-05-24 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H20 Cl3 N O4' _chemical_formula_sum 'C19 H20 Cl3 N O4' _chemical_formula_weight 432.71 _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 trigonal _space_group_IT_number 145 _space_group_name_H-M_alt 'P 32' _space_group_name_Hall 'P 32' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y, x-y, z+2/3' 3 '-x+y, -x, z+1/3' _cell_length_a 11.6604(10) _cell_length_b 11.6604(10) _cell_length_c 27.212(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3204.2(5) _cell_formula_units_Z 6 _cell_measurement_reflns_used 2362 _cell_measurement_temperature 295.90(10) _cell_measurement_theta_max 21.3510 _cell_measurement_theta_min 3.5390 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.23804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1344 _exptl_crystal_size_max 0.3700 _exptl_crystal_size_mid 0.3500 _exptl_crystal_size_min 0.2400 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0655 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 7776 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.67 _diffrn_reflns_theta_min 3.02 _diffrn_ambient_temperature 295.90(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9977 _diffrn_measured_fraction_theta_max 0.6046 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 23.00 86.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -154.0000 54.0000 63 #__ type_ start__ end____ width___ exp.time_ 2 omega 6.00 32.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -57.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega 25.00 84.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -19.0000 -60.0000 59 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0219757000 _diffrn_orient_matrix_UB_12 -0.0452435000 _diffrn_orient_matrix_UB_13 0.0064549000 _diffrn_orient_matrix_UB_21 0.0019765000 _diffrn_orient_matrix_UB_22 0.0177933000 _diffrn_orient_matrix_UB_23 0.0250123000 _diffrn_orient_matrix_UB_31 -0.0665488000 _diffrn_orient_matrix_UB_32 -0.0502663000 _diffrn_orient_matrix_UB_33 0.0029786000 _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 3946 _reflns_number_total 5737 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.273 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(10) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 493 _refine_ls_number_reflns 5737 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0654 _refine_ls_restrained_S_all 1.064 _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^)+(0.0836P)^2^+0.1274P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1576 _refine_ls_wR_factor_ref 0.1878 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C7(H7), C11(H11), C26(H26), C30(H30) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C27(H27A,H27B) 2.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C31(H31), C32(H32) 2.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B, H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 -1.0502(5) -1.0844(3) -0.30296(14) 0.193(2) Uani 1 1 d . . . Cl2 Cl -0.8608(3) -0.8139(4) -0.27710(8) 0.1440(13) Uani 1 1 d . . . Cl3 Cl -1.1329(3) -0.9187(2) -0.25784(8) 0.1128(8) Uani 1 1 d . . . Cl4 Cl -0.5850(3) -0.2315(3) -0.55160(7) 0.1228(10) Uani 1 1 d . . . Cl5 Cl -0.7568(2) -0.1256(3) -0.56013(7) 0.1043(7) Uani 1 1 d . . . Cl6 Cl -0.5032(3) 0.0321(3) -0.51607(12) 0.1464(13) Uani 1 1 d . . . O1 O -1.1325(6) -0.8787(7) -0.3606(2) 0.1028(19) Uani 1 1 d . . . O2 O -0.5904(6) -0.5030(7) -0.4689(2) 0.107(2) Uani 1 1 d . . . O3 O -0.8187(7) -0.4826(6) -0.4790(2) 0.112(2) Uani 1 1 d . . . O4 O -0.9832(5) -0.6732(4) -0.50876(15) 0.0723(12) Uani 1 1 d . . . O5 O -0.7919(5) -0.1913(6) -0.45983(17) 0.0844(15) Uani 1 1 d . . . O6 O -0.6365(6) -0.5782(6) -0.35884(19) 0.0928(16) Uani 1 1 d . . . O7 O -0.8745(7) -0.5761(6) -0.3489(2) 0.1040(19) Uani 1 1 d . . . O8 O -0.8282(4) -0.3864(4) -0.31243(14) 0.0639(11) Uani 1 1 d . . . N1 N -0.8072(6) -0.6728(6) -0.47684(18) 0.0672(14) Uani 1 1 d . . . N2 N -0.6660(6) -0.3976(5) -0.34958(17) 0.0616(13) Uani 1 1 d . . . C1 C -1.0360(8) -1.1234(7) -0.4406(3) 0.079(2) Uani 1 1 d . . . H1 H -0.9529 -1.0954 -0.4271 0.095 Uiso 1 1 calc R . . C2 C -1.1188(9) -1.2559(7) -0.4507(3) 0.084(2) Uani 1 1 d . . . H2 H -1.0898 -1.3157 -0.4445 0.100 Uiso 1 1 calc R . . C3 C -1.2403(8) -1.3002(8) -0.4693(2) 0.078(2) Uani 1 1 d . . . H3 H -1.2960 -1.3901 -0.4751 0.093 Uiso 1 1 calc R . . C4 C -1.2814(7) -1.2123(8) -0.4797(3) 0.0739(19) Uani 1 1 d . . . H4 H -1.3656 -1.2425 -0.4925 0.089 Uiso 1 1 calc R . . C5 C -1.1994(7) -1.0788(7) -0.4714(2) 0.0642(16) Uani 1 1 d . . . H5 H -1.2274 -1.0193 -0.4798 0.077 Uiso 1 1 calc R . . C6 C -1.0752(6) -1.0326(6) -0.4504(2) 0.0572(14) Uani 1 1 d . . . C7 C -0.9870(6) -0.8852(6) -0.4408(2) 0.0553(14) Uani 1 1 d . . . H7 H -1.0427 -0.8446 -0.4440 0.066 Uiso 1 1 calc R . . C8 C -0.9311(6) -0.8574(6) -0.3876(2) 0.0566(14) Uani 1 1 d . . . H8A H -0.8932 -0.9130 -0.3804 0.068 Uiso 1 1 calc R . . H8B H -0.8613 -0.7657 -0.3849 0.068 Uiso 1 1 calc R . . C9 C -1.0361(7) -0.8840(7) -0.3517(2) 0.0651(16) Uani 1 1 d . . . C10 C -1.0194(9) -0.9207(8) -0.2989(3) 0.091(2) Uani 1 1 d . . . C11 C -0.8757(7) -0.8195(7) -0.4798(2) 0.0663(16) Uani 1 1 d . . . H11 H -0.9142 -0.8477 -0.5126 0.080 Uiso 1 1 calc R . . C12 C -0.7632(8) -0.8436(9) -0.4744(2) 0.080(2) Uani 1 1 d . . . H12 H -0.7704 -0.9267 -0.4754 0.096 Uiso 1 1 calc R . . C13 C -0.6518(8) -0.7316(10) -0.4678(3) 0.085(2) Uani 1 1 d . . . H13 H -0.5703 -0.7256 -0.4622 0.102 Uiso 1 1 calc R . . C14 C -0.6714(8) -0.6205(10) -0.4706(2) 0.084(2) Uani 1 1 d . . . C15 C -0.8681(8) -0.5970(8) -0.4873(2) 0.0732(19) Uani 1 1 d . . . C16 C -1.0705(7) -0.6210(7) -0.5236(3) 0.0751(18) Uani 1 1 d . . . C17 C -1.0002(12) -0.5142(12) -0.5608(4) 0.144(5) Uani 1 1 d . . . H17A H -0.9499 -0.4307 -0.5443 0.217 Uiso 1 1 calc R . . H17B H -1.0638 -0.5106 -0.5822 0.217 Uiso 1 1 calc R . . H17C H -0.9417 -0.5324 -0.5797 0.217 Uiso 1 1 calc R . . C18 C -1.1022(17) -0.5692(17) -0.4777(5) 0.175(6) Uani 1 1 d . . . H18A H -1.1039 -0.6207 -0.4499 0.262 Uiso 1 1 calc R . . H18B H -1.1872 -0.5757 -0.4813 0.262 Uiso 1 1 calc R . . H18C H -1.0357 -0.4782 -0.4727 0.262 Uiso 1 1 calc R . . C19 C -1.1841(10) -0.7383(10) -0.5467(4) 0.123(4) Uani 1 1 d . . . H19A H -1.1541 -0.7643 -0.5752 0.185 Uiso 1 1 calc R . . H19B H -1.2501 -0.7163 -0.5562 0.185 Uiso 1 1 calc R . . H19C H -1.2216 -0.8100 -0.5235 0.185 Uiso 1 1 calc R . . C20 C -0.4325(7) 0.0513(7) -0.3787(3) 0.0772(19) Uani 1 1 d . . . H20 H -0.3767 0.0197 -0.3882 0.093 Uiso 1 1 calc R . . C21 C -0.3788(9) 0.1870(8) -0.3697(3) 0.098(3) Uani 1 1 d . . . H21 H -0.2879 0.2443 -0.3719 0.117 Uiso 1 1 calc R . . C22 C -0.4623(10) 0.2348(9) -0.3573(3) 0.088(2) Uani 1 1 d . . . H22 H -0.4275 0.3249 -0.3517 0.105 Uiso 1 1 calc R . . C23 C -0.5943(8) 0.1511(8) -0.3533(3) 0.0759(19) Uani 1 1 d . . . H23 H -0.6509 0.1832 -0.3458 0.091 Uiso 1 1 calc R . . C24 C -0.6436(7) 0.0171(7) -0.3605(2) 0.0681(17) Uani 1 1 d . . . H24 H -0.7339 -0.0401 -0.3562 0.082 Uiso 1 1 calc R . . C25 C -0.5662(6) -0.0362(6) -0.37386(18) 0.0546(14) Uani 1 1 d . . . C26 C -0.6266(6) -0.1827(6) -0.38409(19) 0.0549(14) Uani 1 1 d . . . H26 H -0.7225 -0.2223 -0.3798 0.066 Uiso 1 1 calc R . . C27 C -0.6041(6) -0.2086(6) -0.43751(19) 0.0548(13) Uani 1 1 d . . . H27A H -0.5113 -0.1532 -0.4460 0.066 Uiso 1 1 calc R . . H27B H -0.6272 -0.3004 -0.4413 0.066 Uiso 1 1 calc R . . C28 C -0.6879(7) -0.1785(7) -0.4712(2) 0.0597(15) Uani 1 1 d . . . C29 C -0.6356(7) -0.1293(8) -0.5233(2) 0.0725(18) Uani 1 1 d . . . C30 C -0.5808(6) -0.2527(6) -0.3470(2) 0.0599(15) Uani 1 1 d . . . H30 H -0.5837 -0.2226 -0.3136 0.072 Uiso 1 1 calc R . . C31 C -0.4480(7) -0.2376(8) -0.3561(2) 0.0720(19) Uani 1 1 d . . . H31 H -0.3693 -0.1568 -0.3570 0.086 Uiso 1 1 calc R . . C32 C -0.4565(9) -0.3538(9) -0.3626(3) 0.082(2) Uani 1 1 d . . . H32 H -0.3852 -0.3660 -0.3692 0.098 Uiso 1 1 calc R . . C33 C -0.5926(9) -0.4594(8) -0.3580(2) 0.0746(19) Uani 1 1 d . . . C34 C -0.7987(8) -0.4655(7) -0.3377(2) 0.0657(17) Uani 1 1 d . . . C35 C -0.9659(8) -0.4276(7) -0.2970(2) 0.0738(18) Uani 1 1 d . . . C36 C -0.9476(11) -0.3082(10) -0.2704(4) 0.114(3) Uani 1 1 d . . . H36A H -0.8804 -0.2837 -0.2457 0.171 Uiso 1 1 calc R . . H36B H -1.0294 -0.3274 -0.2550 0.171 Uiso 1 1 calc R . . H36C H -0.9211 -0.2365 -0.2932 0.171 Uiso 1 1 calc R . . C37 C -1.0469(11) -0.4490(15) -0.3425(4) 0.151(5) Uani 1 1 d . . . H37A H -1.0054 -0.3707 -0.3626 0.226 Uiso 1 1 calc R . . H37B H -1.1341 -0.4674 -0.3335 0.226 Uiso 1 1 calc R . . H37C H -1.0532 -0.5225 -0.3607 0.226 Uiso 1 1 calc R . . C38 C -1.0194(11) -0.5437(10) -0.2639(4) 0.119(4) Uani 1 1 d . . . H38A H -1.0109 -0.6132 -0.2793 0.179 Uiso 1 1 calc R . . H38B H -1.1111 -0.5742 -0.2574 0.179 Uiso 1 1 calc R . . H38C H -0.9708 -0.5190 -0.2336 0.179 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 0.338(6) 0.135(3) 0.174(3) 0.085(2) 0.142(3) 0.168(3) Cl2 0.1009(17) 0.260(4) 0.0616(12) 0.0210(16) 0.0000(11) 0.083(2) Cl3 0.1211(19) 0.1067(16) 0.1001(16) 0.0146(12) 0.0586(13) 0.0491(15) Cl4 0.168(2) 0.217(3) 0.0528(10) 0.0041(12) 0.0110(11) 0.148(2) Cl5 0.1193(17) 0.150(2) 0.0685(11) 0.0045(11) -0.0262(10) 0.0861(17) Cl6 0.115(2) 0.113(2) 0.145(2) 0.0509(17) -0.0247(16) 0.0063(17) O1 0.078(4) 0.155(6) 0.097(4) -0.017(4) 0.004(3) 0.074(4) O2 0.075(4) 0.108(5) 0.081(3) 0.013(3) 0.001(3) 0.003(4) O3 0.139(6) 0.057(3) 0.119(4) -0.021(3) -0.056(4) 0.033(3) O4 0.083(3) 0.063(3) 0.066(3) 0.000(2) -0.008(2) 0.033(3) O5 0.069(3) 0.127(5) 0.069(3) 0.000(3) -0.007(2) 0.058(3) O6 0.132(5) 0.089(4) 0.085(3) 0.013(3) 0.025(3) 0.076(4) O7 0.103(4) 0.066(3) 0.123(4) -0.026(3) 0.019(3) 0.028(3) O8 0.074(3) 0.064(3) 0.053(2) -0.0049(18) 0.0059(19) 0.034(2) N1 0.065(4) 0.065(3) 0.052(3) 0.005(2) -0.002(2) 0.017(3) N2 0.082(4) 0.059(3) 0.050(3) -0.008(2) -0.001(2) 0.040(3) C1 0.081(5) 0.066(5) 0.098(5) -0.019(4) -0.031(4) 0.043(4) C2 0.107(6) 0.059(4) 0.087(5) -0.015(4) -0.023(4) 0.043(4) C3 0.080(5) 0.060(4) 0.071(4) -0.017(3) -0.004(4) 0.018(4) C4 0.051(4) 0.084(5) 0.075(4) -0.018(4) -0.006(3) 0.025(4) C5 0.062(4) 0.077(5) 0.055(3) -0.007(3) -0.004(3) 0.036(4) C6 0.054(4) 0.066(4) 0.048(3) -0.005(3) -0.005(2) 0.028(3) C7 0.060(4) 0.051(3) 0.054(3) 0.000(2) -0.002(3) 0.028(3) C8 0.052(3) 0.055(3) 0.060(3) 0.004(3) 0.009(3) 0.025(3) C9 0.053(4) 0.066(4) 0.069(4) -0.008(3) 0.002(3) 0.024(3) C10 0.105(6) 0.088(6) 0.088(5) 0.025(4) 0.033(4) 0.055(5) C11 0.066(4) 0.064(4) 0.055(3) 0.000(3) 0.001(3) 0.022(3) C12 0.073(5) 0.101(6) 0.073(4) 0.006(4) 0.014(3) 0.048(5) C13 0.057(4) 0.128(7) 0.071(5) 0.020(4) 0.012(3) 0.046(5) C14 0.057(4) 0.107(7) 0.057(4) 0.016(4) 0.005(3) 0.016(5) C15 0.089(5) 0.068(5) 0.047(3) 0.001(3) -0.012(3) 0.028(4) C16 0.079(5) 0.070(5) 0.078(4) 0.005(3) 0.001(3) 0.039(4) C17 0.149(10) 0.120(9) 0.142(9) 0.065(7) -0.015(7) 0.051(8) C18 0.219(16) 0.245(18) 0.138(10) -0.032(10) 0.011(10) 0.174(15) C19 0.090(7) 0.095(7) 0.172(9) 0.017(6) -0.040(6) 0.037(6) C20 0.064(5) 0.064(4) 0.100(5) -0.006(4) 0.003(4) 0.029(4) C21 0.080(6) 0.068(5) 0.125(7) -0.013(4) -0.014(5) 0.021(5) C22 0.105(7) 0.077(5) 0.091(5) -0.017(4) -0.017(4) 0.052(5) C23 0.079(5) 0.064(5) 0.091(5) -0.004(3) -0.004(4) 0.041(4) C24 0.065(4) 0.072(5) 0.071(4) 0.001(3) -0.001(3) 0.037(4) C25 0.061(4) 0.063(4) 0.040(3) -0.003(2) -0.002(2) 0.031(3) C26 0.058(4) 0.058(4) 0.047(3) 0.000(2) -0.001(2) 0.027(3) C27 0.054(3) 0.059(3) 0.048(3) -0.006(2) -0.004(2) 0.026(3) C28 0.056(4) 0.072(4) 0.051(3) -0.012(3) -0.012(3) 0.033(3) C29 0.076(5) 0.089(5) 0.052(3) 0.010(3) -0.008(3) 0.042(4) C30 0.073(4) 0.063(4) 0.042(3) -0.003(2) -0.004(3) 0.032(3) C31 0.058(4) 0.093(6) 0.060(4) 0.012(3) -0.005(3) 0.035(4) C32 0.098(6) 0.103(6) 0.068(4) 0.011(4) 0.006(4) 0.067(6) C33 0.105(6) 0.076(5) 0.057(4) 0.011(3) 0.016(3) 0.056(5) C34 0.082(5) 0.060(4) 0.047(3) -0.006(3) 0.005(3) 0.030(4) C35 0.079(5) 0.079(5) 0.060(4) -0.001(3) -0.001(3) 0.037(4) C36 0.144(9) 0.103(7) 0.121(7) 0.004(5) 0.038(6) 0.080(7) C37 0.098(7) 0.230(15) 0.112(8) -0.031(8) -0.036(6) 0.073(9) C38 0.127(8) 0.107(7) 0.126(8) 0.046(6) 0.064(6) 0.060(7) _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 C10 1.761(9) . ? Cl2 C10 1.738(10) . ? Cl3 C10 1.741(8) . ? Cl4 C29 1.750(8) . ? Cl5 C29 1.751(7) . ? Cl6 C29 1.749(8) . ? O1 C9 1.181(8) . ? O2 C14 1.215(10) . ? O3 C15 1.181(9) . ? O4 C15 1.319(8) . ? O4 C16 1.481(9) . ? O5 C28 1.187(7) . ? O6 C33 1.213(9) . ? O7 C34 1.182(8) . ? O8 C34 1.326(8) . ? O8 C35 1.488(9) . ? N1 C11 1.485(9) . ? N1 C14 1.394(9) . ? N1 C15 1.412(10) . ? N2 C30 1.472(8) . ? N2 C33 1.386(9) . ? N2 C34 1.379(9) . ? C1 H1 0.9300 . ? C1 C2 1.379(10) . ? C1 C6 1.374(9) . ? C2 H2 0.9300 . ? C2 C3 1.341(11) . ? C3 H3 0.9300 . ? C3 C4 1.360(11) . ? C4 H4 0.9300 . ? C4 C5 1.378(10) . ? C5 H5 0.9300 . ? C5 C6 1.391(9) . ? C6 C7 1.520(8) . ? C7 H7 0.9800 . ? C7 C8 1.553(9) . ? C7 C11 1.551(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.473(9) . ? C9 C10 1.538(11) . ? C11 H11 0.9800 . ? C11 C12 1.479(10) . ? C12 H12 0.9300 . ? C12 C13 1.315(12) . ? C13 H13 0.9300 . ? C13 C14 1.426(12) . ? C16 C17 1.491(12) . ? C16 C18 1.514(13) . ? C16 C19 1.485(12) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20 0.9300 . ? C20 C21 1.402(11) . ? C20 C25 1.378(9) . ? C21 H21 0.9300 . ? C21 C22 1.383(12) . ? C22 H22 0.9300 . ? C22 C23 1.353(11) . ? C23 H23 0.9300 . ? C23 C24 1.383(10) . ? C24 H24 0.9300 . ? C24 C25 1.376(9) . ? C25 C26 1.514(8) . ? C26 H26 0.9800 . ? C26 C27 1.534(8) . ? C26 C30 1.552(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 C28 1.505(8) . ? C28 C29 1.536(9) . ? C30 H30 0.9800 . ? C30 C31 1.489(9) . ? C31 H31 0.9300 . ? C31 C32 1.320(11) . ? C32 H32 0.9300 . ? C32 C33 1.448(12) . ? C35 C36 1.487(11) . ? C35 C37 1.502(12) . ? C35 C38 1.479(11) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? 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 O4 C16 121.4(6) . . ? C34 O8 C35 122.3(5) . . ? C14 N1 C11 110.5(6) . . ? C14 N1 C15 124.5(6) . . ? C15 N1 C11 124.2(6) . . ? C33 N2 C30 111.5(6) . . ? C34 N2 C30 124.5(5) . . ? C34 N2 C33 123.2(6) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C6 C1 C2 120.6(7) . . ? C1 C2 H2 119.3 . . ? C3 C2 C1 121.3(7) . . ? C3 C2 H2 119.3 . . ? C2 C3 H3 120.3 . . ? C2 C3 C4 119.3(7) . . ? C4 C3 H3 120.3 . . ? C3 C4 H4 119.6 . . ? C3 C4 C5 120.7(6) . . ? C5 C4 H4 119.6 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.3(7) . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 117.7(6) . . ? C1 C6 C7 122.7(6) . . ? C5 C6 C7 119.6(6) . . ? C6 C7 H7 107.0 . . ? C6 C7 C8 111.8(5) . . ? C6 C7 C11 111.5(5) . . ? C8 C7 H7 107.0 . . ? C11 C7 H7 107.0 . . ? C11 C7 C8 112.0(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? C9 C8 C7 110.9(5) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? O1 C9 C8 124.4(6) . . ? O1 C9 C10 117.5(6) . . ? C8 C9 C10 118.1(6) . . ? Cl2 C10 Cl1 111.4(5) . . ? Cl2 C10 Cl3 108.3(5) . . ? Cl3 C10 Cl1 108.1(4) . . ? C9 C10 Cl1 104.9(6) . . ? C9 C10 Cl2 110.9(5) . . ? C9 C10 Cl3 113.1(6) . . ? N1 C11 C7 111.5(5) . . ? N1 C11 H11 109.2 . . ? C7 C11 H11 109.2 . . ? C12 C11 N1 101.3(6) . . ? C12 C11 C7 116.1(6) . . ? C12 C11 H11 109.2 . . ? C11 C12 H12 124.6 . . ? C13 C12 C11 110.8(8) . . ? C13 C12 H12 124.6 . . ? C12 C13 H13 124.2 . . ? C12 C13 C14 111.6(7) . . ? C14 C13 H13 124.2 . . ? O2 C14 N1 124.8(9) . . ? O2 C14 C13 129.4(8) . . ? N1 C14 C13 105.7(7) . . ? O3 C15 O4 127.1(8) . . ? O3 C15 N1 123.7(7) . . ? O4 C15 N1 109.1(6) . . ? O4 C16 C17 109.0(7) . . ? O4 C16 C18 107.1(7) . . ? O4 C16 C19 102.6(6) . . ? C17 C16 C18 111.6(10) . . ? C19 C16 C17 110.4(8) . . ? C19 C16 C18 115.7(10) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 H20 119.3 . . ? C25 C20 H20 119.3 . . ? C25 C20 C21 121.4(7) . . ? C20 C21 H21 120.3 . . ? C22 C21 C20 119.3(8) . . ? C22 C21 H21 120.3 . . ? C21 C22 H22 119.8 . . ? C23 C22 C21 120.3(8) . . ? C23 C22 H22 119.8 . . ? C22 C23 H23 120.5 . . ? C22 C23 C24 118.9(7) . . ? C24 C23 H23 120.5 . . ? C23 C24 H24 118.3 . . ? C25 C24 C23 123.5(7) . . ? C25 C24 H24 118.3 . . ? C20 C25 C26 122.3(6) . . ? C24 C25 C20 116.5(6) . . ? C24 C25 C26 121.2(6) . . ? C25 C26 H26 106.7 . . ? C25 C26 C27 111.6(5) . . ? C25 C26 C30 112.7(5) . . ? C27 C26 H26 106.7 . . ? C27 C26 C30 112.1(5) . . ? C30 C26 H26 106.7 . . ? C26 C27 H27A 109.7 . . ? C26 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? C28 C27 C26 109.7(5) . . ? C28 C27 H27A 109.7 . . ? C28 C27 H27B 109.7 . . ? O5 C28 C27 123.6(5) . . ? O5 C28 C29 118.6(5) . . ? C27 C28 C29 117.8(6) . . ? Cl4 C29 Cl5 108.4(4) . . ? Cl6 C29 Cl4 111.4(4) . . ? Cl6 C29 Cl5 109.1(4) . . ? C28 C29 Cl4 111.0(5) . . ? C28 C29 Cl5 111.3(5) . . ? C28 C29 Cl6 105.7(5) . . ? N2 C30 C26 111.1(5) . . ? N2 C30 H30 109.4 . . ? N2 C30 C31 101.1(6) . . ? C26 C30 H30 109.4 . . ? C31 C30 C26 116.2(5) . . ? C31 C30 H30 109.4 . . ? C30 C31 H31 124.4 . . ? C32 C31 C30 111.1(7) . . ? C32 C31 H31 124.4 . . ? C31 C32 H32 124.8 . . ? C31 C32 C33 110.5(7) . . ? C33 C32 H32 124.8 . . ? O6 C33 N2 125.4(8) . . ? O6 C33 C32 128.8(8) . . ? N2 C33 C32 105.7(7) . . ? O7 C34 O8 125.5(7) . . ? O7 C34 N2 125.3(6) . . ? O8 C34 N2 109.2(6) . . ? O8 C35 C37 108.0(7) . . ? C36 C35 O8 102.0(6) . . ? C36 C35 C37 110.0(9) . . ? C38 C35 O8 111.1(7) . . ? C38 C35 C36 110.9(7) . . ? C38 C35 C37 114.1(9) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36B 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37B 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38B 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 O1 C9 C10 Cl1 106.3(8) . . . . ? O1 C9 C10 Cl2 -133.2(7) . . . . ? O1 C9 C10 Cl3 -11.2(10) . . . . ? O5 C28 C29 Cl4 -130.2(6) . . . . ? O5 C28 C29 Cl5 -9.4(9) . . . . ? O5 C28 C29 Cl6 108.9(7) . . . . ? N1 C11 C12 C13 1.8(7) . . . . ? N2 C30 C31 C32 -0.1(6) . . . . ? C1 C2 C3 C4 1.9(12) . . . . ? C1 C6 C7 C8 -51.4(8) . . . . ? C1 C6 C7 C11 74.9(7) . . . . ? C2 C1 C6 C5 -1.0(10) . . . . ? C2 C1 C6 C7 -178.9(6) . . . . ? C2 C3 C4 C5 0.1(11) . . . . ? C3 C4 C5 C6 -2.5(10) . . . . ? C4 C5 C6 C1 2.9(9) . . . . ? C4 C5 C6 C7 -179.1(5) . . . . ? C5 C6 C7 C8 130.7(6) . . . . ? C5 C6 C7 C11 -103.0(7) . . . . ? C6 C1 C2 C3 -1.4(12) . . . . ? C6 C7 C8 C9 -71.3(7) . . . . ? C6 C7 C11 N1 168.2(5) . . . . ? C6 C7 C11 C12 -76.4(7) . . . . ? C7 C8 C9 O1 -26.0(10) . . . . ? C7 C8 C9 C10 154.2(6) . . . . ? C7 C11 C12 C13 -119.2(7) . . . . ? C8 C7 C11 N1 -65.6(7) . . . . ? C8 C7 C11 C12 49.8(8) . . . . ? C8 C9 C10 Cl1 -73.8(7) . . . . ? C8 C9 C10 Cl2 46.6(8) . . . . ? C8 C9 C10 Cl3 168.6(5) . . . . ? C11 N1 C14 O2 177.1(7) . . . . ? C11 N1 C14 C13 -1.9(7) . . . . ? C11 N1 C15 O3 170.1(7) . . . . ? C11 N1 C15 O4 -12.1(8) . . . . ? C11 C7 C8 C9 162.7(5) . . . . ? C11 C12 C13 C14 -3.1(8) . . . . ? C12 C13 C14 O2 -175.8(7) . . . . ? C12 C13 C14 N1 3.1(8) . . . . ? C14 N1 C11 C7 124.3(6) . . . . ? C14 N1 C11 C12 0.2(6) . . . . ? C14 N1 C15 O3 -21.3(10) . . . . ? C14 N1 C15 O4 156.5(6) . . . . ? C15 O4 C16 C17 61.8(9) . . . . ? C15 O4 C16 C18 -59.1(10) . . . . ? C15 O4 C16 C19 178.7(7) . . . . ? C15 N1 C11 C7 -65.7(7) . . . . ? C15 N1 C11 C12 170.2(5) . . . . ? C15 N1 C14 O2 7.1(11) . . . . ? C15 N1 C14 C13 -171.8(6) . . . . ? C16 O4 C15 O3 -2.9(11) . . . . ? C16 O4 C15 N1 179.4(5) . . . . ? C20 C21 C22 C23 0.9(13) . . . . ? C20 C25 C26 C27 -60.8(7) . . . . ? C20 C25 C26 C30 66.2(7) . . . . ? C21 C20 C25 C24 1.0(10) . . . . ? C21 C20 C25 C26 179.1(7) . . . . ? C21 C22 C23 C24 1.6(12) . . . . ? C22 C23 C24 C25 -3.0(11) . . . . ? C23 C24 C25 C20 1.7(9) . . . . ? C23 C24 C25 C26 -176.5(6) . . . . ? C24 C25 C26 C27 117.2(6) . . . . ? C24 C25 C26 C30 -115.7(6) . . . . ? C25 C20 C21 C22 -2.3(12) . . . . ? C25 C26 C27 C28 -71.0(6) . . . . ? C25 C26 C30 N2 165.1(5) . . . . ? C25 C26 C30 C31 -80.1(7) . . . . ? C26 C27 C28 O5 -30.6(9) . . . . ? C26 C27 C28 C29 149.7(6) . . . . ? C26 C30 C31 C32 -120.4(6) . . . . ? C27 C26 C30 N2 -68.1(6) . . . . ? C27 C26 C30 C31 46.7(7) . . . . ? C27 C28 C29 Cl4 49.4(7) . . . . ? C27 C28 C29 Cl5 170.3(5) . . . . ? C27 C28 C29 Cl6 -71.5(7) . . . . ? C30 N2 C33 O6 175.3(7) . . . . ? C30 N2 C33 C32 -1.8(7) . . . . ? C30 N2 C34 O7 163.3(7) . . . . ? C30 N2 C34 O8 -15.6(8) . . . . ? C30 C26 C27 C28 161.6(5) . . . . ? C30 C31 C32 C33 -1.0(8) . . . . ? C31 C32 C33 O6 -175.2(7) . . . . ? C31 C32 C33 N2 1.7(8) . . . . ? C33 N2 C30 C26 125.0(6) . . . . ? C33 N2 C30 C31 1.2(6) . . . . ? C33 N2 C34 O7 -27.3(10) . . . . ? C33 N2 C34 O8 153.9(6) . . . . ? C34 O8 C35 C36 179.7(7) . . . . ? C34 O8 C35 C37 -64.4(9) . . . . ? C34 O8 C35 C38 61.4(9) . . . . ? C34 N2 C30 C26 -64.4(7) . . . . ? C34 N2 C30 C31 171.7(5) . . . . ? C34 N2 C33 O6 4.6(10) . . . . ? C34 N2 C33 C32 -172.4(5) . . . . ? C35 O8 C34 O7 -3.0(10) . . . . ? C35 O8 C34 N2 175.8(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 941172'