# Electronic Supplementary Material (ESI) for RSC Advances # 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_global data_a20913a #TrackingRef 'a20913a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H18 Cl2 N2 O' _chemical_formula_weight 493.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.781(4) _cell_length_b 10.430(4) _cell_length_c 13.144(5) _cell_angle_alpha 87.774(5) _cell_angle_beta 82.039(6) _cell_angle_gamma 80.848(5) _cell_volume 1176.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 840 _cell_measurement_theta_min 2.370 _cell_measurement_theta_max 26.554 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8367 _exptl_absorpt_correction_T_max 0.9474 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5.05 _diffrn_reflns_number 4899 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4061 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1390P)^2^+0.1909P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4061 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.2337 _refine_ls_wR_factor_gt 0.2005 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.5938(2) -0.15184(12) 0.63127(12) 0.1208(6) Uani 1 1 d . . . Cl2 Cl 0.06739(14) -0.09887(11) 1.19443(9) 0.0910(4) Uani 1 1 d . . . N1 N 0.3336(3) 0.4878(3) 0.73330(18) 0.0530(7) Uani 1 1 d . . . N2 N 0.3394(3) 0.3550(3) 0.87933(19) 0.0534(7) Uani 1 1 d . . . O1 O 0.2700(3) 0.6761(2) 0.82006(19) 0.0777(8) Uani 1 1 d . . . C1 C 0.2616(4) 0.6157(3) 0.7441(2) 0.0533(8) Uani 1 1 d . . . C2 C 0.3240(3) 0.4109(3) 0.6498(2) 0.0522(8) Uani 1 1 d . . . C3 C 0.2492(4) 0.4637(3) 0.5719(2) 0.0578(8) Uani 1 1 d . . . H3 H 0.2465 0.4134 0.5155 0.069 Uiso 1 1 calc R . . C4 C 0.1738(4) 0.5956(3) 0.5743(2) 0.0552(8) Uani 1 1 d . . . C5 C 0.0891(4) 0.6520(4) 0.4957(3) 0.0683(10) Uani 1 1 d . . . H5 H 0.0841 0.6041 0.4384 0.082 Uiso 1 1 calc R . . C6 C 0.0140(5) 0.7777(4) 0.5043(3) 0.0806(12) Uani 1 1 d . . . H6 H -0.0410 0.8147 0.4521 0.097 Uiso 1 1 calc R . . C7 C 0.0189(5) 0.8498(4) 0.5888(3) 0.0782(11) Uani 1 1 d . . . H7 H -0.0338 0.9345 0.5939 0.094 Uiso 1 1 calc R . . C8 C 0.1011(4) 0.7972(3) 0.6653(3) 0.0643(9) Uani 1 1 d . . . H8 H 0.1053 0.8468 0.7219 0.077 Uiso 1 1 calc R . . C9 C 0.1781(4) 0.6706(3) 0.6593(2) 0.0522(8) Uani 1 1 d . . . C10 C 0.3965(4) 0.2731(3) 0.6506(2) 0.0527(8) Uani 1 1 d . . . C11 C 0.3133(5) 0.1799(4) 0.6971(3) 0.0758(11) Uani 1 1 d . . . H11 H 0.2151 0.2053 0.7333 0.091 Uiso 1 1 calc R . . C12 C 0.3741(5) 0.0490(4) 0.6905(4) 0.0812(12) Uani 1 1 d . . . H12 H 0.3173 -0.0132 0.7218 0.097 Uiso 1 1 calc R . . C13 C 0.5178(5) 0.0130(4) 0.6376(3) 0.0778(11) Uani 1 1 d . . . C14 C 0.6028(5) 0.1019(5) 0.5926(4) 0.0918(14) Uani 1 1 d . . . H14 H 0.7019 0.0759 0.5578 0.110 Uiso 1 1 calc R . . C15 C 0.5409(5) 0.2313(4) 0.5988(3) 0.0792(11) Uani 1 1 d . . . H15 H 0.5989 0.2923 0.5668 0.095 Uiso 1 1 calc R . . C16 C 0.4154(4) 0.4299(3) 0.8174(2) 0.0505(7) Uani 1 1 d . . . C17 C 0.5672(4) 0.4572(3) 0.8219(2) 0.0520(8) Uani 1 1 d . . . C18 C 0.6469(4) 0.5356(4) 0.7528(3) 0.0647(9) Uani 1 1 d . . . H18 H 0.6004 0.5741 0.6974 0.078 Uiso 1 1 calc R . . C19 C 0.7927(4) 0.5570(4) 0.7653(3) 0.0760(10) Uani 1 1 d . . . H19 H 0.8445 0.6106 0.7192 0.091 Uiso 1 1 calc R . . C20 C 0.8639(4) 0.4976(4) 0.8483(3) 0.0750(11) Uani 1 1 d . . . H20 H 0.9640 0.5107 0.8558 0.090 Uiso 1 1 calc R . . C21 C 0.7894(4) 0.4220(4) 0.9171(3) 0.0649(9) Uani 1 1 d . . . H21 H 0.8375 0.3860 0.9726 0.078 Uiso 1 1 calc R . . C22 C 0.6382(4) 0.3962(3) 0.9064(2) 0.0545(8) Uani 1 1 d . . . C23 C 0.5571(4) 0.3150(3) 0.9730(2) 0.0557(8) Uani 1 1 d . . . H23 H 0.6020 0.2757 1.0287 0.067 Uiso 1 1 calc R . . C24 C 0.4126(4) 0.2922(3) 0.9578(2) 0.0524(8) Uani 1 1 d . . . C25 C 0.3254(4) 0.2005(3) 1.0199(2) 0.0560(8) Uani 1 1 d . . . C26 C 0.3979(5) 0.1056(4) 1.0830(3) 0.0744(11) Uani 1 1 d . . . H26 H 0.5024 0.1038 1.0894 0.089 Uiso 1 1 calc R . . C27 C 0.3185(5) 0.0151(4) 1.1355(3) 0.0763(11) Uani 1 1 d . . . H27 H 0.3696 -0.0483 1.1759 0.092 Uiso 1 1 calc R . . C28 C 0.1651(4) 0.0181(4) 1.1285(3) 0.0669(9) Uani 1 1 d . . . C29 C 0.0895(5) 0.1111(4) 1.0685(3) 0.0807(11) Uani 1 1 d . . . H29 H -0.0159 0.1139 1.0645 0.097 Uiso 1 1 calc R . . C30 C 0.1702(4) 0.1999(4) 1.0143(3) 0.0730(10) Uani 1 1 d . . . H30 H 0.1186 0.2614 0.9727 0.088 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 0.1490(13) 0.0690(7) 0.1403(12) -0.0090(7) -0.0562(10) 0.0288(7) Cl2 0.1007(9) 0.0775(7) 0.0906(8) 0.0125(5) 0.0038(6) -0.0183(6) N1 0.0513(15) 0.0594(16) 0.0469(14) 0.0051(12) -0.0163(11) 0.0025(11) N2 0.0498(15) 0.0620(17) 0.0475(14) 0.0015(12) -0.0165(12) 0.0023(12) O1 0.0926(19) 0.0751(17) 0.0633(15) -0.0153(13) -0.0352(14) 0.0183(14) C1 0.0506(18) 0.0587(19) 0.0510(17) 0.0029(15) -0.0149(14) -0.0033(14) C2 0.0446(17) 0.064(2) 0.0472(16) 0.0035(14) -0.0094(13) -0.0040(14) C3 0.063(2) 0.064(2) 0.0490(17) -0.0001(14) -0.0194(15) -0.0068(15) C4 0.0523(18) 0.065(2) 0.0491(17) 0.0138(15) -0.0133(14) -0.0100(14) C5 0.075(2) 0.075(2) 0.059(2) 0.0109(17) -0.0313(18) -0.0098(18) C6 0.086(3) 0.082(3) 0.078(3) 0.028(2) -0.040(2) -0.006(2) C7 0.081(3) 0.071(2) 0.081(3) 0.015(2) -0.033(2) 0.0057(19) C8 0.068(2) 0.060(2) 0.065(2) 0.0045(16) -0.0222(17) -0.0021(16) C9 0.0456(17) 0.0602(19) 0.0509(17) 0.0120(14) -0.0115(13) -0.0073(13) C10 0.0482(18) 0.063(2) 0.0477(16) 0.0039(14) -0.0151(14) -0.0046(14) C11 0.059(2) 0.072(3) 0.092(3) 0.000(2) -0.003(2) -0.0041(18) C12 0.079(3) 0.061(2) 0.110(3) 0.004(2) -0.026(2) -0.0169(19) C13 0.086(3) 0.068(2) 0.077(2) -0.004(2) -0.033(2) 0.016(2) C14 0.072(3) 0.087(3) 0.099(3) 0.014(2) 0.007(2) 0.021(2) C15 0.063(2) 0.079(3) 0.085(3) 0.017(2) 0.004(2) 0.0044(19) C16 0.0513(17) 0.0549(18) 0.0442(16) 0.0011(14) -0.0166(13) 0.0035(13) C17 0.0485(18) 0.0560(18) 0.0498(16) -0.0039(14) -0.0121(14) 0.0028(13) C18 0.059(2) 0.068(2) 0.065(2) 0.0071(17) -0.0152(17) -0.0009(16) C19 0.062(2) 0.083(3) 0.083(3) 0.006(2) -0.009(2) -0.0107(19) C20 0.051(2) 0.087(3) 0.087(3) -0.006(2) -0.0173(19) -0.0021(18) C21 0.0516(19) 0.071(2) 0.073(2) -0.0014(18) -0.0216(17) 0.0017(16) C22 0.0490(18) 0.0549(18) 0.0570(18) -0.0066(15) -0.0164(14) 0.0093(13) C23 0.0556(19) 0.0595(19) 0.0504(17) 0.0007(14) -0.0226(15) 0.0096(14) C24 0.0520(18) 0.0573(18) 0.0449(16) -0.0006(13) -0.0155(14) 0.0080(13) C25 0.055(2) 0.065(2) 0.0430(16) 0.0031(14) -0.0089(14) 0.0069(15) C26 0.066(2) 0.092(3) 0.062(2) 0.025(2) -0.0201(18) -0.0010(19) C27 0.082(3) 0.084(3) 0.058(2) 0.0224(19) -0.0150(19) 0.003(2) C28 0.070(2) 0.068(2) 0.0565(19) 0.0014(16) -0.0005(17) -0.0020(17) C29 0.060(2) 0.091(3) 0.085(3) 0.016(2) -0.011(2) 0.003(2) C30 0.059(2) 0.078(3) 0.076(2) 0.0224(19) -0.0137(18) 0.0041(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 C13 1.743(4) . ? Cl2 C28 1.738(4) . ? N1 C1 1.386(4) . ? N1 C2 1.404(4) . ? N1 C16 1.460(4) . ? N2 C16 1.298(4) . ? N2 C24 1.379(4) . ? O1 C1 1.217(4) . ? C1 C9 1.467(4) . ? C2 C3 1.345(4) . ? C2 C10 1.477(5) . ? C3 C4 1.428(5) . ? C3 H3 0.9300 . ? C4 C9 1.397(5) . ? C4 C5 1.412(4) . ? C5 C6 1.372(6) . ? C5 H5 0.9300 . ? C6 C7 1.375(6) . ? C6 H6 0.9300 . ? C7 C8 1.366(5) . ? C7 H7 0.9300 . ? C8 C9 1.384(5) . ? C8 H8 0.9300 . ? C10 C15 1.367(5) . ? C10 C11 1.382(5) . ? C11 C12 1.385(5) . ? C11 H11 0.9300 . ? C12 C13 1.357(6) . ? C12 H12 0.9300 . ? C13 C14 1.350(6) . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.416(4) . ? C17 C18 1.390(5) . ? C17 C22 1.427(4) . ? C18 C19 1.366(5) . ? C18 H18 0.9300 . ? C19 C20 1.407(6) . ? C19 H19 0.9300 . ? C20 C21 1.346(5) . ? C20 H20 0.9300 . ? C21 C22 1.422(5) . ? C21 H21 0.9300 . ? C22 C23 1.398(5) . ? C23 C24 1.370(5) . ? C23 H23 0.9300 . ? C24 C25 1.472(5) . ? C25 C30 1.376(5) . ? C25 C26 1.398(5) . ? C26 C27 1.371(6) . ? C26 H26 0.9300 . ? C27 C28 1.358(6) . ? C27 H27 0.9300 . ? C28 C29 1.373(5) . ? C29 C30 1.373(6) . ? C29 H29 0.9300 . ? C30 H30 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 C1 N1 C2 123.6(2) . . ? C1 N1 C16 117.0(2) . . ? C2 N1 C16 119.3(3) . . ? C16 N2 C24 117.9(3) . . ? O1 C1 N1 120.6(3) . . ? O1 C1 C9 123.7(3) . . ? N1 C1 C9 115.7(3) . . ? C3 C2 N1 119.6(3) . . ? C3 C2 C10 121.9(3) . . ? N1 C2 C10 118.5(3) . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C9 C4 C5 118.4(3) . . ? C9 C4 C3 119.1(3) . . ? C5 C4 C3 122.5(3) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 121.0(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C4 120.3(3) . . ? C8 C9 C1 119.1(3) . . ? C4 C9 C1 120.6(3) . . ? C15 C10 C11 117.5(3) . . ? C15 C10 C2 122.1(3) . . ? C11 C10 C2 120.2(3) . . ? C10 C11 C12 121.0(4) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 119.0(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C14 C13 C12 121.4(4) . . ? C14 C13 Cl1 120.1(4) . . ? C12 C13 Cl1 118.6(4) . . ? C13 C14 C15 119.1(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C10 C15 C14 122.0(4) . . ? C10 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? N2 C16 C17 127.0(3) . . ? N2 C16 N1 114.7(3) . . ? C17 C16 N1 118.2(3) . . ? C18 C17 C16 125.6(3) . . ? C18 C17 C22 120.1(3) . . ? C16 C17 C22 114.3(3) . . ? C19 C18 C17 120.8(3) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 119.6(4) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.1(3) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 123.8(3) . . ? C23 C22 C17 118.9(3) . . ? C21 C22 C17 117.3(3) . . ? C24 C23 C22 121.2(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 N2 120.6(3) . . ? C23 C24 C25 124.2(3) . . ? N2 C24 C25 115.1(3) . . ? C30 C25 C26 116.8(3) . . ? C30 C25 C24 121.4(3) . . ? C26 C25 C24 121.7(3) . . ? C27 C26 C25 121.5(4) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C28 C27 C26 119.9(3) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.2(4) . . ? C27 C28 Cl2 119.1(3) . . ? C29 C28 Cl2 120.7(3) . . ? C28 C29 C30 119.7(4) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C29 C30 C25 121.9(3) . . ? C29 C30 H30 119.1 . . ? C25 C30 H30 119.1 . . ? 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 C2 N1 C1 O1 177.5(3) . . . . ? C16 N1 C1 O1 1.3(5) . . . . ? C2 N1 C1 C9 -2.7(4) . . . . ? C16 N1 C1 C9 -179.0(3) . . . . ? C1 N1 C2 C3 4.0(5) . . . . ? C16 N1 C2 C3 -179.8(3) . . . . ? C1 N1 C2 C10 -175.7(3) . . . . ? C16 N1 C2 C10 0.4(4) . . . . ? N1 C2 C3 C4 -2.5(5) . . . . ? C10 C2 C3 C4 177.3(3) . . . . ? C2 C3 C4 C9 -0.1(5) . . . . ? C2 C3 C4 C5 -177.3(3) . . . . ? C9 C4 C5 C6 0.2(5) . . . . ? C3 C4 C5 C6 177.4(3) . . . . ? C4 C5 C6 C7 -0.5(6) . . . . ? C5 C6 C7 C8 0.9(7) . . . . ? C6 C7 C8 C9 -0.9(6) . . . . ? C7 C8 C9 C4 0.6(5) . . . . ? C7 C8 C9 C1 -178.3(3) . . . . ? C5 C4 C9 C8 -0.2(5) . . . . ? C3 C4 C9 C8 -177.6(3) . . . . ? C5 C4 C9 C1 178.7(3) . . . . ? C3 C4 C9 C1 1.3(5) . . . . ? O1 C1 C9 C8 -1.3(5) . . . . ? N1 C1 C9 C8 179.0(3) . . . . ? O1 C1 C9 C4 179.8(3) . . . . ? N1 C1 C9 C4 0.1(4) . . . . ? C3 C2 C10 C15 82.1(4) . . . . ? N1 C2 C10 C15 -98.2(4) . . . . ? C3 C2 C10 C11 -92.1(4) . . . . ? N1 C2 C10 C11 87.6(4) . . . . ? C15 C10 C11 C12 -0.5(6) . . . . ? C2 C10 C11 C12 174.0(3) . . . . ? C10 C11 C12 C13 0.2(6) . . . . ? C11 C12 C13 C14 0.8(7) . . . . ? C11 C12 C13 Cl1 179.2(3) . . . . ? C12 C13 C14 C15 -1.4(7) . . . . ? Cl1 C13 C14 C15 -179.8(3) . . . . ? C11 C10 C15 C14 -0.2(6) . . . . ? C2 C10 C15 C14 -174.5(4) . . . . ? C13 C14 C15 C10 1.1(7) . . . . ? C24 N2 C16 C17 -1.1(5) . . . . ? C24 N2 C16 N1 177.1(3) . . . . ? C1 N1 C16 N2 100.8(3) . . . . ? C2 N1 C16 N2 -75.6(4) . . . . ? C1 N1 C16 C17 -80.8(4) . . . . ? C2 N1 C16 C17 102.8(3) . . . . ? N2 C16 C17 C18 178.4(3) . . . . ? N1 C16 C17 C18 0.3(5) . . . . ? N2 C16 C17 C22 -1.7(5) . . . . ? N1 C16 C17 C22 -179.8(3) . . . . ? C16 C17 C18 C19 179.0(3) . . . . ? C22 C17 C18 C19 -0.9(5) . . . . ? C17 C18 C19 C20 0.8(6) . . . . ? C18 C19 C20 C21 -1.4(6) . . . . ? C19 C20 C21 C22 2.1(6) . . . . ? C20 C21 C22 C23 177.7(3) . . . . ? C20 C21 C22 C17 -2.1(5) . . . . ? C18 C17 C22 C23 -178.3(3) . . . . ? C16 C17 C22 C23 1.8(4) . . . . ? C18 C17 C22 C21 1.5(5) . . . . ? C16 C17 C22 C21 -178.4(3) . . . . ? C21 C22 C23 C24 -179.0(3) . . . . ? C17 C22 C23 C24 0.8(5) . . . . ? C22 C23 C24 N2 -3.7(5) . . . . ? C22 C23 C24 C25 175.2(3) . . . . ? C16 N2 C24 C23 3.9(4) . . . . ? C16 N2 C24 C25 -175.2(3) . . . . ? C23 C24 C25 C30 167.3(3) . . . . ? N2 C24 C25 C30 -13.7(5) . . . . ? C23 C24 C25 C26 -16.3(5) . . . . ? N2 C24 C25 C26 162.7(3) . . . . ? C30 C25 C26 C27 0.9(6) . . . . ? C24 C25 C26 C27 -175.7(3) . . . . ? C25 C26 C27 C28 -1.3(6) . . . . ? C26 C27 C28 C29 0.3(6) . . . . ? C26 C27 C28 Cl2 179.2(3) . . . . ? C27 C28 C29 C30 1.0(6) . . . . ? Cl2 C28 C29 C30 -177.8(3) . . . . ? C28 C29 C30 C25 -1.4(7) . . . . ? C26 C25 C30 C29 0.5(6) . . . . ? C24 C25 C30 C29 177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.288 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 921037'