# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Yong-Ming Liang' 'Yan-Fang Yang' 'Xing-Zhong Shu' 'Hai-Long Wei' ; Jian-Yi Luo ; S.Ali 'Xue-Yuan Liu' _publ_contact_author_email yangm2008@lzu.cn data_p21n _database_code_depnum_ccdc_archive 'CCDC 807037' #TrackingRef 'P21n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 Cl2 N2' _chemical_formula_weight 487.44 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4142(9) _cell_length_b 16.6090(17) _cell_length_c 16.8295(17) _cell_angle_alpha 90.00 _cell_angle_beta 105.1730(10) _cell_angle_gamma 90.00 _cell_volume 2539.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3405 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 24.43 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9093 _exptl_absorpt_correction_T_max 0.9265 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12994 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4692 _reflns_number_gt 3442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0458P)^2^+0.5208P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4692 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.003 _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 C1 C -0.0502(2) 0.15425(11) 0.12786(11) 0.0411(4) Uani 1 1 d . . . C2 C -0.1716(2) 0.15331(11) 0.16020(12) 0.0452(5) Uani 1 1 d . . . H2 H -0.2046 0.1050 0.1769 0.054 Uiso 1 1 calc R . . C3 C -0.2434(2) 0.22499(12) 0.16742(12) 0.0467(5) Uani 1 1 d . . . C4 C -0.1888(2) 0.29555(12) 0.14085(13) 0.0515(5) Uani 1 1 d . . . H4 H -0.2354 0.3443 0.1444 0.062 Uiso 1 1 calc R . . C5 C -0.0681(2) 0.29428(11) 0.10975(12) 0.0492(5) Uani 1 1 d . . . H5 H -0.0353 0.3426 0.0929 0.059 Uiso 1 1 calc R . . C6 C 0.0079(2) 0.22352(11) 0.10225(11) 0.0408(4) Uani 1 1 d . . . C7 C 0.1363(2) 0.22130(11) 0.06391(11) 0.0410(4) Uani 1 1 d . . . H7 H 0.1889 0.1711 0.0830 0.049 Uiso 1 1 calc R . . C8 C 0.0834(2) 0.21439(11) -0.03133(12) 0.0438(4) Uani 1 1 d . . . H8 H 0.0272 0.1641 -0.0430 0.053 Uiso 1 1 calc R . . C9 C 0.2184(2) 0.20333(11) -0.06539(12) 0.0441(5) Uani 1 1 d . . . H9 H 0.1839 0.2053 -0.1256 0.053 Uiso 1 1 calc R . . C10 C 0.3374(2) 0.30823(11) 0.03424(12) 0.0425(4) Uani 1 1 d . . . C11 C 0.4386(2) 0.37186(11) 0.05651(13) 0.0485(5) Uani 1 1 d . . . H11 H 0.4947 0.3876 0.0212 0.058 Uiso 1 1 calc R . . C12 C 0.4548(2) 0.41088(11) 0.13065(13) 0.0495(5) Uani 1 1 d . . . C13 C 0.3778(2) 0.38911(12) 0.18576(13) 0.0536(5) Uani 1 1 d . . . H13 H 0.3941 0.4142 0.2367 0.064 Uiso 1 1 calc R . . C14 C 0.2746(2) 0.32810(12) 0.16278(12) 0.0493(5) Uani 1 1 d . . . H14 H 0.2196 0.3135 0.1991 0.059 Uiso 1 1 calc R . . C15 C 0.2497(2) 0.28800(11) 0.08843(11) 0.0419(4) Uani 1 1 d . . . C16 C 0.2897(2) 0.12006(12) -0.04195(14) 0.0591(6) Uani 1 1 d . . . H16A H 0.3320 0.1188 0.0171 0.071 Uiso 1 1 calc R . . H16B H 0.2129 0.0795 -0.0551 0.071 Uiso 1 1 calc R . . C17 C 0.4073(2) 0.09725(11) -0.08340(13) 0.0467(5) Uani 1 1 d . . . C18 C 0.5530(3) 0.09223(14) -0.04045(15) 0.0625(6) Uani 1 1 d . . . H18 H 0.5807 0.1048 0.0153 0.075 Uiso 1 1 calc R . . C19 C 0.6590(3) 0.06861(16) -0.07930(19) 0.0776(8) Uani 1 1 d . . . H19 H 0.7568 0.0646 -0.0493 0.093 Uiso 1 1 calc R . . C20 C 0.6206(3) 0.05116(15) -0.1612(2) 0.0807(8) Uani 1 1 d . . . H20 H 0.6921 0.0359 -0.1873 0.097 Uiso 1 1 calc R . . C21 C 0.4773(3) 0.05619(15) -0.20454(16) 0.0806(8) Uani 1 1 d . . . H21 H 0.4507 0.0446 -0.2606 0.097 Uiso 1 1 calc R . . C22 C 0.3712(3) 0.07841(14) -0.16593(14) 0.0651(6) Uani 1 1 d . . . H22 H 0.2733 0.0807 -0.1962 0.078 Uiso 1 1 calc R . . C23 C -0.0200(2) 0.28100(12) -0.07411(12) 0.0482(5) Uani 1 1 d . . . C24 C -0.1583(2) 0.25922(15) -0.12226(13) 0.0612(6) Uani 1 1 d . . . H24 H -0.1845 0.2051 -0.1269 0.073 Uiso 1 1 calc R . . C25 C -0.2580(3) 0.3162(2) -0.16346(15) 0.0790(8) Uani 1 1 d . . . H25 H -0.3493 0.3000 -0.1961 0.095 Uiso 1 1 calc R . . C26 C -0.2227(3) 0.3961(2) -0.15632(17) 0.0859(9) Uani 1 1 d . . . H26 H -0.2904 0.4345 -0.1831 0.103 Uiso 1 1 calc R . . C27 C -0.0870(3) 0.41950(16) -0.10952(17) 0.0814(8) Uani 1 1 d . . . H27 H -0.0624 0.4738 -0.1049 0.098 Uiso 1 1 calc R . . C28 C 0.0141(3) 0.36250(13) -0.06886(14) 0.0656(6) Uani 1 1 d . . . H28 H 0.1061 0.3792 -0.0376 0.079 Uiso 1 1 calc R . . C29 C -0.4370(3) 0.15729(15) 0.21763(15) 0.0711(7) Uani 1 1 d . . . H29A H -0.4661 0.1252 0.1686 0.107 Uiso 1 1 calc R . . H29B H -0.5225 0.1726 0.2349 0.107 Uiso 1 1 calc R . . H29C H -0.3719 0.1267 0.2604 0.107 Uiso 1 1 calc R . . C30 C 0.4138(3) 0.29163(14) -0.09368(14) 0.0667(7) Uani 1 1 d . . . H30A H 0.3965 0.3470 -0.1095 0.100 Uiso 1 1 calc R . . H30B H 0.3901 0.2583 -0.1420 0.100 Uiso 1 1 calc R . . H30C H 0.5155 0.2844 -0.0650 0.100 Uiso 1 1 calc R . . Cl1 Cl 0.02797(6) 0.05979(3) 0.11802(4) 0.06205(18) Uani 1 1 d . . . Cl2 Cl 0.58041(7) 0.49069(3) 0.15414(4) 0.0702(2) Uani 1 1 d . . . N1 N 0.32141(18) 0.26906(10) -0.03974(10) 0.0501(4) Uani 1 1 d . . . N2 N -0.3624(2) 0.22842(13) 0.20098(12) 0.0621(5) Uani 1 1 d . . . H1N H -0.410(3) 0.2731(15) 0.1933(15) 0.079(8) Uiso 1 1 d . . . 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 C1 0.0419(11) 0.0388(10) 0.0423(11) 0.0042(8) 0.0107(9) 0.0058(8) C2 0.0463(11) 0.0438(11) 0.0475(11) 0.0075(9) 0.0158(9) 0.0002(9) C3 0.0426(11) 0.0545(12) 0.0447(11) 0.0054(9) 0.0143(9) 0.0039(9) C4 0.0482(12) 0.0443(11) 0.0651(13) 0.0010(10) 0.0200(10) 0.0084(9) C5 0.0485(12) 0.0388(10) 0.0646(13) 0.0047(9) 0.0224(10) 0.0016(9) C6 0.0407(11) 0.0412(10) 0.0419(10) 0.0032(8) 0.0132(9) 0.0031(8) C7 0.0410(11) 0.0390(10) 0.0450(11) 0.0036(8) 0.0148(9) 0.0041(8) C8 0.0454(11) 0.0398(10) 0.0477(11) -0.0010(8) 0.0146(9) 0.0007(9) C9 0.0494(12) 0.0414(10) 0.0437(11) -0.0014(8) 0.0160(9) 0.0032(9) C10 0.0430(11) 0.0369(10) 0.0488(11) 0.0034(8) 0.0140(9) 0.0042(8) C11 0.0468(12) 0.0426(11) 0.0584(13) 0.0068(10) 0.0177(10) 0.0010(9) C12 0.0435(11) 0.0370(10) 0.0639(14) -0.0003(10) 0.0069(10) 0.0008(9) C13 0.0553(13) 0.0524(13) 0.0517(13) -0.0084(10) 0.0115(10) 0.0024(10) C14 0.0490(12) 0.0530(12) 0.0491(12) 0.0004(10) 0.0184(10) 0.0028(10) C15 0.0399(11) 0.0418(10) 0.0454(11) 0.0026(8) 0.0136(9) 0.0047(8) C16 0.0677(15) 0.0463(12) 0.0715(15) 0.0041(10) 0.0330(12) 0.0080(11) C17 0.0524(13) 0.0364(10) 0.0541(12) 0.0022(9) 0.0187(10) 0.0068(9) C18 0.0649(15) 0.0608(14) 0.0588(14) 0.0059(11) 0.0106(12) 0.0051(12) C19 0.0483(14) 0.0778(18) 0.107(2) 0.0255(16) 0.0203(15) 0.0117(12) C20 0.087(2) 0.0731(17) 0.101(2) 0.0239(15) 0.0581(18) 0.0310(15) C21 0.108(2) 0.0779(18) 0.0622(16) -0.0027(13) 0.0339(16) 0.0319(16) C22 0.0629(15) 0.0674(15) 0.0628(15) -0.0104(12) 0.0123(12) 0.0131(12) C23 0.0487(12) 0.0570(13) 0.0424(11) 0.0039(9) 0.0178(9) 0.0105(10) C24 0.0475(13) 0.0800(16) 0.0575(14) 0.0074(12) 0.0162(11) 0.0067(12) C25 0.0508(15) 0.122(3) 0.0646(16) 0.0144(16) 0.0153(12) 0.0238(16) C26 0.082(2) 0.110(2) 0.0709(18) 0.0245(17) 0.0279(16) 0.0552(19) C27 0.104(2) 0.0663(16) 0.0750(18) 0.0121(14) 0.0248(17) 0.0312(16) C28 0.0736(16) 0.0538(13) 0.0633(15) 0.0076(11) 0.0071(12) 0.0162(12) C29 0.0633(15) 0.0837(17) 0.0766(17) 0.0136(13) 0.0365(13) -0.0008(13) C30 0.0872(17) 0.0577(14) 0.0704(15) -0.0034(11) 0.0475(14) -0.0140(12) Cl1 0.0666(4) 0.0395(3) 0.0878(4) 0.0085(3) 0.0341(3) 0.0103(2) Cl2 0.0649(4) 0.0474(3) 0.0917(5) -0.0047(3) 0.0085(3) -0.0109(3) N1 0.0562(10) 0.0482(9) 0.0530(10) -0.0045(8) 0.0268(9) -0.0089(8) N2 0.0566(12) 0.0628(12) 0.0770(14) 0.0132(10) 0.0356(10) 0.0118(10) _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 C1 C2 1.389(3) . ? C1 C6 1.390(2) . ? C1 Cl1 1.7588(18) . ? C2 C3 1.390(3) . ? C2 H2 0.9300 . ? C3 N2 1.382(2) . ? C3 C4 1.399(3) . ? C4 C5 1.370(3) . ? C4 H4 0.9300 . ? C5 C6 1.399(2) . ? C5 H5 0.9300 . ? C6 C7 1.512(2) . ? C7 C15 1.519(3) . ? C7 C8 1.553(3) . ? C7 H7 0.9800 . ? C8 C23 1.524(3) . ? C8 C9 1.536(3) . ? C8 H8 0.9800 . ? C9 N1 1.449(2) . ? C9 C16 1.543(3) . ? C9 H9 0.9800 . ? C10 N1 1.378(2) . ? C10 C11 1.407(3) . ? C10 C15 1.421(2) . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 C13 1.366(3) . ? C12 Cl2 1.751(2) . ? C13 C14 1.387(3) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C16 C17 1.504(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.376(3) . ? C17 C22 1.377(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9300 . ? C19 C20 1.361(4) . ? C19 H19 0.9300 . ? C20 C21 1.358(4) . ? C20 H20 0.9300 . ? C21 C22 1.377(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.389(3) . ? C23 C28 1.389(3) . ? C24 C25 1.385(3) . ? C24 H24 0.9300 . ? C25 C26 1.366(4) . ? C25 H25 0.9300 . ? C26 C27 1.370(4) . ? C26 H26 0.9300 . ? C27 C28 1.389(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 N2 1.439(3) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 N1 1.461(2) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? N2 H1N 0.86(2) . ? 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 C2 C1 C6 124.16(17) . . ? C2 C1 Cl1 115.74(14) . . ? C6 C1 Cl1 120.08(14) . . ? C1 C2 C3 119.58(17) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? N2 C3 C2 122.41(19) . . ? N2 C3 C4 120.06(19) . . ? C2 C3 C4 117.52(17) . . ? C5 C4 C3 121.32(18) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 122.85(18) . . ? C4 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? C1 C6 C5 114.56(16) . . ? C1 C6 C7 122.35(16) . . ? C5 C6 C7 122.96(16) . . ? C6 C7 C15 116.73(15) . . ? C6 C7 C8 111.46(15) . . ? C15 C7 C8 110.31(14) . . ? C6 C7 H7 105.8 . . ? C15 C7 H7 105.8 . . ? C8 C7 H7 105.8 . . ? C23 C8 C9 113.53(15) . . ? C23 C8 C7 115.25(15) . . ? C9 C8 C7 108.70(15) . . ? C23 C8 H8 106.2 . . ? C9 C8 H8 106.2 . . ? C7 C8 H8 106.2 . . ? N1 C9 C8 110.70(15) . . ? N1 C9 C16 112.77(17) . . ? C8 C9 C16 111.02(15) . . ? N1 C9 H9 107.4 . . ? C8 C9 H9 107.4 . . ? C16 C9 H9 107.4 . . ? N1 C10 C11 120.11(17) . . ? N1 C10 C15 121.60(17) . . ? C11 C10 C15 118.25(17) . . ? C12 C11 C10 120.07(18) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 122.50(19) . . ? C13 C12 Cl2 119.58(16) . . ? C11 C12 Cl2 117.92(16) . . ? C12 C13 C14 117.46(19) . . ? C12 C13 H13 121.3 . . ? C14 C13 H13 121.3 . . ? C15 C14 C13 123.01(18) . . ? C15 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? C14 C15 C10 118.53(17) . . ? C14 C15 C7 122.54(16) . . ? C10 C15 C7 118.89(16) . . ? C17 C16 C9 115.53(17) . . ? C17 C16 H16A 108.4 . . ? C9 C16 H16A 108.4 . . ? C17 C16 H16B 108.4 . . ? C9 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C22 117.7(2) . . ? C18 C17 C16 121.7(2) . . ? C22 C17 C16 120.5(2) . . ? C17 C18 C19 120.8(2) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 119.6(2) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.3(2) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 121.3(2) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? C24 C23 C28 117.2(2) . . ? C24 C23 C8 118.14(19) . . ? C28 C23 C8 124.68(19) . . ? C25 C24 C23 121.5(2) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 119.7(2) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C26 C27 C28 120.4(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 121.0(2) . . ? C27 C28 H28 119.5 . . ? C23 C28 H28 119.5 . . ? N2 C29 H29A 109.5 . . ? N2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N1 C30 H30A 109.5 . . ? N1 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N1 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C10 N1 C9 122.09(15) . . ? C10 N1 C30 119.90(17) . . ? C9 N1 C30 117.98(16) . . ? C3 N2 C29 122.3(2) . . ? C3 N2 H1N 114.9(17) . . ? C29 N2 H1N 118.4(17) . . ? 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 C6 C1 C2 C3 0.8(3) . . . . ? Cl1 C1 C2 C3 -177.74(15) . . . . ? C1 C2 C3 N2 -178.32(19) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? N2 C3 C4 C5 177.91(19) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C2 C1 C6 C5 -1.3(3) . . . . ? Cl1 C1 C6 C5 177.14(14) . . . . ? C2 C1 C6 C7 -177.25(17) . . . . ? Cl1 C1 C6 C7 1.2(2) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C4 C5 C6 C7 176.75(18) . . . . ? C1 C6 C7 C15 -140.76(18) . . . . ? C5 C6 C7 C15 43.7(3) . . . . ? C1 C6 C7 C8 91.3(2) . . . . ? C5 C6 C7 C8 -84.3(2) . . . . ? C6 C7 C8 C23 57.3(2) . . . . ? C15 C7 C8 C23 -74.1(2) . . . . ? C6 C7 C8 C9 -174.02(14) . . . . ? C15 C7 C8 C9 54.62(19) . . . . ? C23 C8 C9 N1 72.9(2) . . . . ? C7 C8 C9 N1 -56.79(19) . . . . ? C23 C8 C9 C16 -161.06(18) . . . . ? C7 C8 C9 C16 69.3(2) . . . . ? N1 C10 C11 C12 -179.82(18) . . . . ? C15 C10 C11 C12 2.4(3) . . . . ? C10 C11 C12 C13 1.5(3) . . . . ? C10 C11 C12 Cl2 -178.98(14) . . . . ? C11 C12 C13 C14 -3.5(3) . . . . ? Cl2 C12 C13 C14 177.02(15) . . . . ? C12 C13 C14 C15 1.6(3) . . . . ? C13 C14 C15 C10 2.3(3) . . . . ? C13 C14 C15 C7 -179.96(18) . . . . ? N1 C10 C15 C14 178.08(18) . . . . ? C11 C10 C15 C14 -4.2(3) . . . . ? N1 C10 C15 C7 0.2(3) . . . . ? C11 C10 C15 C7 177.97(16) . . . . ? C6 C7 C15 C14 26.3(3) . . . . ? C8 C7 C15 C14 154.85(17) . . . . ? C6 C7 C15 C10 -155.92(16) . . . . ? C8 C7 C15 C10 -27.4(2) . . . . ? N1 C9 C16 C17 -64.7(2) . . . . ? C8 C9 C16 C17 170.42(18) . . . . ? C9 C16 C17 C18 110.5(2) . . . . ? C9 C16 C17 C22 -71.3(3) . . . . ? C22 C17 C18 C19 -0.3(3) . . . . ? C16 C17 C18 C19 177.9(2) . . . . ? C17 C18 C19 C20 1.0(4) . . . . ? C18 C19 C20 C21 -0.7(4) . . . . ? C19 C20 C21 C22 -0.3(4) . . . . ? C20 C21 C22 C17 1.1(4) . . . . ? C18 C17 C22 C21 -0.7(3) . . . . ? C16 C17 C22 C21 -179.0(2) . . . . ? C9 C8 C23 C24 112.1(2) . . . . ? C7 C8 C23 C24 -121.65(19) . . . . ? C9 C8 C23 C28 -67.6(3) . . . . ? C7 C8 C23 C28 58.7(3) . . . . ? C28 C23 C24 C25 0.1(3) . . . . ? C8 C23 C24 C25 -179.59(19) . . . . ? C23 C24 C25 C26 -1.1(4) . . . . ? C24 C25 C26 C27 1.3(4) . . . . ? C25 C26 C27 C28 -0.5(4) . . . . ? C26 C27 C28 C23 -0.5(4) . . . . ? C24 C23 C28 C27 0.7(3) . . . . ? C8 C23 C28 C27 -179.7(2) . . . . ? C11 C10 N1 C9 -179.88(17) . . . . ? C15 C10 N1 C9 -2.2(3) . . . . ? C11 C10 N1 C30 2.3(3) . . . . ? C15 C10 N1 C30 -179.95(18) . . . . ? C8 C9 N1 C10 31.4(2) . . . . ? C16 C9 N1 C10 -93.6(2) . . . . ? C8 C9 N1 C30 -150.74(18) . . . . ? C16 C9 N1 C30 84.2(2) . . . . ? C2 C3 N2 C29 -11.1(3) . . . . ? C4 C3 N2 C29 170.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.199 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.037