# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1497 #============================================================================== data_global #============================================================================== _audit_creation_date 09-30-99 _audit_creation_method SHELXL _audit_update_record ; ? ; # 1. SUBMISSION DETAILS _publ_contact_author ; J.Jens Wolff Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_email 'e56@ix.urz.uni-heidelberg.de' _publ_contact_author_fax '(+49) 6221 544205' _publ_contact_author_phone '(+49) 6221 548429' _publ_requested_journal 'J. Chem. Soc. Chem. Commun. ' _publ_requested_coeditor_name ? _publ_contact_letter ; Paper was sent to J. Chem. Soc. Chem. Commun. for publication ; # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; Formation of a benzenetrienoid resonance structure in a cyclophane containing a trinitro-triaminobenzene unit ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Wolff, J.Jens' #<--'Last name, first name' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg ; 'Seibold, Uwe' #<--'Last name, first name' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg ; 'Oeser, Thomas' #<--'Last name, first name' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_experimental ; ? ; _publ_section_references ; Enraf-Nonius, CAD4 Operations Manual, Delft, 1988. International Tables for X-Ray Crystallography, Vol. IV, The Kynoch Press, Birmingham, England, 1974 ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_766us1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,7,8,11,12,15,16,24,31-Nonaaza-10,14,18-trioxo-8,9,12,13,16,17-hexahydro- 26,28,30-trinitro[6(3)](1,5,9)triphenyleno(1,3,5)cyclophane (1a) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33.50 H42 Cl N12 O12' _chemical_formula_weight 840.24 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 trigonal _symmetry_space_group_name_H-M 'P -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 15.267(3) _cell_length_b 15.267(3) _cell_length_c 10.921(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2204(1) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.3 _cell_measurement_theta_max 17.8 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 NONIUS_CAD4 _diffrn_measurement_method \w2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -1 _diffrn_reflns_number 3941 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.073 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3549 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1440P)^2^+0.0000P] 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 3549 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.168 _refine_ls_R_factor_gt 0.067 _refine_ls_wR_factor_ref 0.236 _refine_ls_wR_factor_gt 0.187 _refine_ls_goodness_of_fit_ref 0.98 _refine_ls_restrained_S_all 0.98 _refine_ls_shift/su_max 0.000 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O16 O 0.53725(16) 0.47000(17) 0.2616(3) 0.0614(7) Uani 1 1 d . . . O17 O 0.6114(2) 0.5204(2) 0.0886(3) 0.0779(9) Uani 1 1 d . . . O18 O 0.34212(15) 0.02317(15) 0.8504(2) 0.0543(6) Uani 1 1 d . . . N1 N 0.45862(18) 0.26411(19) 0.1906(2) 0.0428(6) Uani 1 1 d . . . H1 H 0.436(2) 0.311(3) 0.186(3) 0.049(9) Uiso 1 1 d . . . N7 N 0.46528(16) 0.29356(16) 0.8061(2) 0.0384(6) Uani 1 1 d . . . N10 N 0.50595(19) 0.13513(19) 0.8136(3) 0.0418(6) Uani 1 1 d . . . H10 H 0.517(3) 0.095(3) 0.812(3) 0.049(11) Uiso 1 1 d . . . N15 N 0.59110(19) 0.46907(19) 0.1798(3) 0.0471(7) Uani 1 1 d . . . C2 C 0.3760(2) 0.1723(2) 0.2458(3) 0.0476(8) Uani 1 1 d . . . H2B H 0.3675 0.1141 0.1999 0.057 Uiso 1 1 calc R . . H2A H 0.3138 0.1745 0.2381 0.057 Uiso 1 1 calc R . . C3 C 0.3916(3) 0.1579(3) 0.3773(3) 0.0549(9) Uani 1 1 d . . . H3A H 0.4529 0.1540 0.3844 0.066 Uiso 1 1 calc R . . H3B H 0.3358 0.0935 0.4042 0.066 Uiso 1 1 calc R . . C4 C 0.3999(3) 0.2402(3) 0.4638(3) 0.0587(9) Uani 1 1 d . . . H4A H 0.4532 0.3056 0.4357 0.070 Uiso 1 1 calc R . . H4B H 0.3369 0.2412 0.4631 0.070 Uiso 1 1 calc R . . C5 C 0.4225(3) 0.2222(3) 0.5909(3) 0.0553(8) Uani 1 1 d . . . H5A H 0.4853 0.2208 0.5905 0.066 Uiso 1 1 calc R . . H5B H 0.3692 0.1563 0.6177 0.066 Uiso 1 1 calc R . . C6 C 0.4316(2) 0.3010(2) 0.6822(3) 0.0453(8) Uani 1 1 d . . . H6A H 0.4788 0.3673 0.6496 0.054 Uiso 1 1 calc R . . H6B H 0.3663 0.2967 0.6889 0.054 Uiso 1 1 calc R . . C8 C 0.56670(19) 0.3139(2) 0.8119(3) 0.0377(7) Uani 1 1 d . . . C9 C 0.58760(19) 0.23487(19) 0.8139(3) 0.0362(6) Uani 1 1 d . . . C11 C 0.4111(2) 0.1113(2) 0.8427(3) 0.0414(7) Uani 1 1 d . . . C12 C 0.3966(2) 0.1999(2) 0.8711(3) 0.0421(7) Uani 1 1 d . . . H12A H 0.3276 0.1814 0.8510 0.051 Uiso 1 1 calc R . . H12B H 0.4054 0.2129 0.9585 0.051 Uiso 1 1 calc R . . C13 C 0.55966(19) 0.2958(2) 0.1935(3) 0.0363(6) Uani 1 1 d . . . C14 C 0.6314(2) 0.4005(2) 0.1919(3) 0.0386(7) Uani 1 1 d . . . O30 O 0.1835(15) 0.0057(14) 0.997(3) 0.107(7) Uani 0.45 1 d P . . O30A O 0.1759(13) -0.0077(12) 1.010(2) 0.068(5) Uani 0.40 1 d P . . O30B O 0.1551(17) -0.0072(19) 0.9309(19) 0.066(7) Uiso 0.15 1 d P . . Cl1B Cl -0.0271(13) 0.0940(13) 0.6744(15) 0.105(5) Uiso 0.11 1 d P . . Cl1A Cl -0.0686(19) 0.0716(19) 0.657(2) 0.120(7) Uiso 0.11 1 d P . . Cl1 Cl -0.0958(14) 0.0276(15) 0.6731(15) 0.110(5) Uiso 0.11 1 d P . . C50 C 0.018(3) 0.0383(19) 0.745(2) 0.093(10) Uiso 0.17 1 d P . . 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 O16 0.0397(12) 0.0470(13) 0.1022(19) -0.0117(13) 0.0034(13) 0.0251(11) O17 0.100(2) 0.0741(18) 0.084(2) 0.0164(15) -0.0092(16) 0.0623(17) O18 0.0334(11) 0.0323(11) 0.0861(17) -0.0017(11) 0.0094(11) 0.0082(9) N1 0.0293(12) 0.0336(12) 0.0661(17) -0.0033(11) -0.0017(11) 0.0162(10) N7 0.0268(11) 0.0321(12) 0.0566(15) -0.0044(10) 0.0005(10) 0.0149(10) N10 0.0295(12) 0.0258(12) 0.0684(18) -0.0005(11) 0.0054(11) 0.0125(10) N15 0.0352(13) 0.0355(13) 0.0737(19) -0.0093(13) -0.0115(13) 0.0199(11) C2 0.0340(15) 0.0385(16) 0.062(2) -0.0065(14) 0.0042(13) 0.0123(13) C3 0.057(2) 0.0497(19) 0.063(2) -0.0013(16) 0.0036(16) 0.0307(17) C4 0.063(2) 0.052(2) 0.063(2) -0.0059(17) -0.0044(18) 0.0308(17) C5 0.062(2) 0.0437(17) 0.060(2) -0.0024(15) 0.0030(17) 0.0262(16) C6 0.0390(15) 0.0414(16) 0.059(2) -0.0055(14) -0.0027(14) 0.0226(14) C8 0.0275(13) 0.0356(15) 0.0512(17) -0.0032(12) 0.0002(12) 0.0166(11) C9 0.0282(13) 0.0265(13) 0.0499(17) -0.0009(12) 0.0010(11) 0.0105(11) C11 0.0299(14) 0.0335(14) 0.0558(18) -0.0027(13) 0.0008(13) 0.0122(12) C12 0.0283(13) 0.0380(15) 0.0583(18) -0.0037(13) 0.0050(12) 0.0154(12) C13 0.0305(13) 0.0348(14) 0.0442(16) -0.0016(12) -0.0012(12) 0.0168(11) C14 0.0341(15) 0.0312(14) 0.0533(17) -0.0015(12) -0.0031(12) 0.0184(12) O30 0.084(10) 0.081(10) 0.121(13) 0.025(8) 0.012(8) 0.016(7) O30A 0.046(6) 0.027(4) 0.137(14) 0.024(5) 0.048(7) 0.022(4) _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 O16 N15 1.219(4) . ? O17 N15 1.208(4) . ? O18 C11 1.228(3) . ? N1 C13 1.367(3) . ? N1 C2 1.467(4) . ? N1 H1 0.93(4) . ? N7 C8 1.420(3) . ? N7 C12 1.466(4) . ? N7 C6 1.472(4) . ? N10 C11 1.342(4) . ? N10 C9 1.405(3) . ? N10 H10 0.72(3) . ? N15 C14 1.461(3) . ? C2 C3 1.491(5) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C3 C4 1.526(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.488(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.514(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.388(4) 3_665 ? C8 C9 1.393(4) . ? C9 C8 1.388(4) 2_655 ? C11 C12 1.509(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.399(4) 2_655 ? C13 C14 1.416(4) . ? C14 C13 1.399(4) 3_665 ? O30 O30B 0.81(3) . ? O30A O30B 0.92(3) . ? Cl1B Cl1A 0.58(3) . ? Cl1B Cl1 1.03(3) . ? Cl1B C50 1.55(4) . ? Cl1B C50 1.83(5) 2 ? Cl1B Cl1 2.28(3) 3 ? Cl1A Cl1 0.61(3) . ? Cl1A C50 1.90(5) . ? Cl1A C50 1.93(5) 2 ? Cl1 C50 1.60(4) 2 ? Cl1 C50 1.84(5) . ? Cl1 Cl1B 2.28(3) 2 ? C50 C50 0.88(4) 2 ? C50 C50 0.88(4) 3 ? C50 Cl1 1.60(4) 3 ? C50 Cl1B 1.83(5) 3 ? C50 Cl1A 1.93(5) 3 ? 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 N1 C2 127.4(3) . . ? C13 N1 H1 121(2) . . ? C2 N1 H1 107(2) . . ? C8 N7 C12 111.2(2) . . ? C8 N7 C6 114.1(2) . . ? C12 N7 C6 114.4(2) . . ? C11 N10 C9 123.1(3) . . ? C11 N10 H10 117(3) . . ? C9 N10 H10 118(3) . . ? O17 N15 O16 123.5(3) . . ? O17 N15 C14 118.4(3) . . ? O16 N15 C14 118.0(3) . . ? N1 C2 C3 114.3(3) . . ? N1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? N1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? H2B C2 H2A 107.6 . . ? C2 C3 C4 115.4(3) . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3B 108.4 . . ? C4 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C5 C4 C3 110.9(3) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 114.0(3) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N7 C6 C5 116.2(3) . . ? N7 C6 H6A 108.2 . . ? C5 C6 H6A 108.2 . . ? N7 C6 H6B 108.2 . . ? C5 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? C9 C8 C9 118.4(3) 3_665 . ? C9 C8 N7 121.1(2) 3_665 . ? C9 C8 N7 120.5(2) . . ? C8 C9 C8 121.6(3) 2_655 . ? C8 C9 N10 120.0(2) 2_655 . ? C8 C9 N10 118.4(2) . . ? O18 C11 N10 122.1(3) . . ? O18 C11 C12 122.5(3) . . ? N10 C11 C12 115.3(2) . . ? N7 C12 C11 114.9(2) . . ? N7 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? N7 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? N1 C13 C14 124.2(2) . 2_655 ? N1 C13 C14 119.9(2) . . ? C14 C13 C14 115.8(3) 2_655 . ? C13 C14 C13 124.1(3) 3_665 . ? C13 C14 N15 119.3(2) 3_665 . ? C13 C14 N15 116.4(2) . . ? O30 O30B O30A 13(2) . . ? Cl1A Cl1B Cl1 31(3) . . ? Cl1A Cl1B C50 120(4) . . ? Cl1 Cl1B C50 89(2) . . ? Cl1A Cl1B C50 91(4) . 2 ? Cl1 Cl1B C50 60.4(16) . 2 ? C50 Cl1B C50 28.5(19) . 2 ? Cl1A Cl1B Cl1 143(3) . 3 ? Cl1 Cl1B Cl1 122.3(18) . 3 ? C50 Cl1B Cl1 44.3(15) . 3 ? C50 Cl1B Cl1 68.2(11) 2 3 ? Cl1B Cl1A Cl1 120(6) . . ? Cl1B Cl1A C50 45(3) . . ? Cl1 Cl1A C50 75(3) . . ? Cl1B Cl1A C50 71(4) . 2 ? Cl1 Cl1A C50 49(3) . 2 ? C50 Cl1A C50 26.4(15) . 2 ? Cl1A Cl1 Cl1B 29(3) . . ? Cl1A Cl1 C50 114(4) . 2 ? Cl1B Cl1 C50 85(2) . 2 ? Cl1A Cl1 C50 86(4) . . ? Cl1B Cl1 C50 57.0(16) . . ? C50 Cl1 C50 28.4(18) 2 . ? Cl1A Cl1 Cl1B 139(3) . 2 ? Cl1B Cl1 Cl1B 117.7(18) . 2 ? C50 Cl1 Cl1B 42.5(15) 2 2 ? C50 Cl1 Cl1B 66.7(11) . 2 ? C50 C50 C50 60.000(9) 2 3 ? C50 C50 Cl1B 94(6) 2 . ? C50 C50 Cl1B 142(4) 3 . ? C50 C50 Cl1 140(4) 2 3 ? C50 C50 Cl1 92(6) 3 3 ? Cl1B C50 Cl1 93.2(16) . 3 ? C50 C50 Cl1B 111(5) 2 3 ? C50 C50 Cl1B 57(5) 3 3 ? Cl1B C50 Cl1B 118.9(19) . 3 ? Cl1 C50 Cl1B 34.2(13) 3 3 ? C50 C50 Cl1 60(5) 2 . ? C50 C50 Cl1 114(5) 3 . ? Cl1B C50 Cl1 34.1(13) . . ? Cl1 C50 Cl1 119.0(18) 3 . ? Cl1B C50 Cl1 129.0(16) 3 . ? C50 C50 Cl1A 79(5) 2 . ? C50 C50 Cl1A 129(4) 3 . ? Cl1B C50 Cl1A 15.4(12) . . ? Cl1 C50 Cl1A 104.4(16) 3 . ? Cl1B C50 Cl1A 124.0(16) 3 . ? Cl1 C50 Cl1A 18.7(9) . . ? C50 C50 Cl1A 126(4) 2 3 ? C50 C50 Cl1A 75(5) 3 3 ? Cl1B C50 Cl1A 105.3(17) . 3 ? Cl1 C50 Cl1A 16.8(12) 3 3 ? Cl1B C50 Cl1A 17.5(9) 3 3 ? Cl1 C50 Cl1A 124.4(15) . 3 ? Cl1A C50 Cl1A 113.8(17) . 3 ? 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 C13 N1 C2 C3 50.9(4) . . . . ? N1 C2 C3 C4 61.9(4) . . . . ? C2 C3 C4 C5 -176.1(3) . . . . ? C3 C4 C5 C6 -179.9(3) . . . . ? C8 N7 C6 C5 67.0(3) . . . . ? C12 N7 C6 C5 -62.6(3) . . . . ? C4 C5 C6 N7 -173.2(3) . . . . ? C12 N7 C8 C9 -148.0(3) . . . 3_665 ? C6 N7 C8 C9 80.8(3) . . . 3_665 ? C12 N7 C8 C9 32.9(4) . . . . ? C6 N7 C8 C9 -98.3(3) . . . . ? C9 C8 C9 C8 -3.2(6) 3_665 . . 2_655 ? N7 C8 C9 C8 175.97(18) . . . 2_655 ? C9 C8 C9 N10 179.11(19) 3_665 . . . ? N7 C8 C9 N10 -1.7(4) . . . . ? C11 N10 C9 C8 164.6(3) . . . 2_655 ? C11 N10 C9 C8 -17.6(5) . . . . ? C9 N10 C11 O18 -174.7(3) . . . . ? C9 N10 C11 C12 2.5(4) . . . . ? C8 N7 C12 C11 -46.6(3) . . . . ? C6 N7 C12 C11 84.4(3) . . . . ? O18 C11 C12 N7 -152.5(3) . . . . ? N10 C11 C12 N7 30.3(4) . . . . ? C2 N1 C13 C14 34.1(5) . . . 2_655 ? C2 N1 C13 C14 -149.2(3) . . . . ? N1 C13 C14 C13 -179.4(2) . . . 3_665 ? C14 C13 C14 C13 -2.5(6) 2_655 . . 3_665 ? N1 C13 C14 N15 -3.5(4) . . . . ? C14 C13 C14 N15 173.41(18) 2_655 . . . ? O17 N15 C14 C13 61.0(4) . . . 3_665 ? O16 N15 C14 C13 -120.2(3) . . . 3_665 ? O17 N15 C14 C13 -115.1(3) . . . . ? O16 N15 C14 C13 63.7(4) . . . . ? C50 Cl1B Cl1A Cl1 8(8) . . . . ? C50 Cl1B Cl1A Cl1 7(6) 2 . . . ? Cl1 Cl1B Cl1A Cl1 60(9) 3 . . . ? Cl1 Cl1B Cl1A C50 -8(8) . . . . ? C50 Cl1B Cl1A C50 -2(3) 2 . . . ? Cl1 Cl1B Cl1A C50 52(5) 3 . . . ? Cl1 Cl1B Cl1A C50 -7(6) . . . 2 ? C50 Cl1B Cl1A C50 2(3) . . . 2 ? Cl1 Cl1B Cl1A C50 54(5) 3 . . 2 ? C50 Cl1A Cl1 Cl1B 6(6) . . . . ? C50 Cl1A Cl1 Cl1B 8(7) 2 . . . ? Cl1B Cl1A Cl1 C50 -8(7) . . . 2 ? C50 Cl1A Cl1 C50 -2(2) . . . 2 ? Cl1B Cl1A Cl1 C50 -6(6) . . . . ? C50 Cl1A Cl1 C50 2(2) 2 . . . ? Cl1B Cl1A Cl1 Cl1B -53(8) . . . 2 ? C50 Cl1A Cl1 Cl1B -47(4) . . . 2 ? C50 Cl1A Cl1 Cl1B -45(4) 2 . . 2 ? C50 Cl1B Cl1 Cl1A -173(7) . . . . ? C50 Cl1B Cl1 Cl1A -172(7) 2 . . . ? Cl1 Cl1B Cl1 Cl1A -142(6) 3 . . . ? Cl1A Cl1B Cl1 C50 172(7) . . . 2 ? C50 Cl1B Cl1 C50 -0.5(17) . . . 2 ? Cl1 Cl1B Cl1 C50 30(2) 3 . . 2 ? Cl1A Cl1B Cl1 C50 173(7) . . . . ? C50 Cl1B Cl1 C50 0.5(17) 2 . . . ? Cl1 Cl1B Cl1 C50 30.8(16) 3 . . . ? Cl1A Cl1B Cl1 Cl1B 144(6) . . . 2 ? C50 Cl1B Cl1 Cl1B -29(2) . . . 2 ? C50 Cl1B Cl1 Cl1B -28.7(16) 2 . . 2 ? Cl1 Cl1B Cl1 Cl1B 2(3) 3 . . 2 ? Cl1A Cl1B C50 C50 -3(5) . . . 2 ? Cl1 Cl1B C50 C50 1(3) . . . 2 ? Cl1 Cl1B C50 C50 -141(3) 3 . . 2 ? Cl1A Cl1B C50 C50 41(10) . . . 3 ? Cl1 Cl1B C50 C50 45(9) . . . 3 ? C50 Cl1B C50 C50 44(6) 2 . . 3 ? Cl1 Cl1B C50 C50 -97(9) 3 . . 3 ? Cl1A Cl1B C50 Cl1 137(4) . . . 3 ? Cl1 Cl1B C50 Cl1 141.7(18) . . . 3 ? C50 Cl1B C50 Cl1 141(3) 2 . . 3 ? Cl1A Cl1B C50 Cl1B 114(4) . . . 3 ? Cl1 Cl1B C50 Cl1B 117.9(19) . . . 3 ? C50 Cl1B C50 Cl1B 117(3) 2 . . 3 ? Cl1 Cl1B C50 Cl1B -23.8(13) 3 . . 3 ? Cl1A Cl1B C50 Cl1 -4(4) . . . . ? C50 Cl1B C50 Cl1 -1(3) 2 . . . ? Cl1 Cl1B C50 Cl1 -141.7(18) 3 . . . ? Cl1 Cl1B C50 Cl1A 4(4) . . . . ? C50 Cl1B C50 Cl1A 3(5) 2 . . . ? Cl1 Cl1B C50 Cl1A -137(4) 3 . . . ? Cl1A Cl1B C50 Cl1A 126(5) . . . 3 ? Cl1 Cl1B C50 Cl1A 129.9(17) . . . 3 ? C50 Cl1B C50 Cl1A 129(3) 2 . . 3 ? Cl1 Cl1B C50 Cl1A -11.8(11) 3 . . 3 ? Cl1A Cl1 C50 C50 -175(5) . . . 2 ? Cl1B Cl1 C50 C50 -179(3) . . . 2 ? Cl1B Cl1 C50 C50 -27(3) 2 . . 2 ? Cl1A Cl1 C50 C50 -148(4) . . . 3 ? Cl1B Cl1 C50 C50 -151(4) . . . 3 ? C50 Cl1 C50 C50 27.7(9) 2 . . 3 ? Cl1B Cl1 C50 C50 1(3) 2 . . 3 ? Cl1A Cl1 C50 Cl1B 4(3) . . . . ? C50 Cl1 C50 Cl1B 179(3) 2 . . . ? Cl1B Cl1 C50 Cl1B 152.0(19) 2 . . . ? Cl1A Cl1 C50 Cl1 -42(4) . . . 3 ? Cl1B Cl1 C50 Cl1 -45(2) . . . 3 ? C50 Cl1 C50 Cl1 134(4) 2 . . 3 ? Cl1B Cl1 C50 Cl1 107(2) 2 . . 3 ? Cl1A Cl1 C50 Cl1B -81(4) . . . 3 ? Cl1B Cl1 C50 Cl1B -85(2) . . . 3 ? C50 Cl1 C50 Cl1B 94(3) 2 . . 3 ? Cl1B Cl1 C50 Cl1B 67.1(18) 2 . . 3 ? Cl1B Cl1 C50 Cl1A -4(3) . . . . ? C50 Cl1 C50 Cl1A 175(5) 2 . . . ? Cl1B Cl1 C50 Cl1A 148(3) 2 . . . ? Cl1A Cl1 C50 Cl1A -60(4) . . . 3 ? Cl1B Cl1 C50 Cl1A -64(2) . . . 3 ? C50 Cl1 C50 Cl1A 115(3) 2 . . 3 ? Cl1B Cl1 C50 Cl1A 88.2(18) 2 . . 3 ? Cl1B Cl1A C50 C50 177(5) . . . 2 ? Cl1 Cl1A C50 C50 4(4) . . . 2 ? Cl1B Cl1A C50 C50 -148(7) . . . 3 ? Cl1 Cl1A C50 C50 39(6) . . . 3 ? C50 Cl1A C50 C50 35(3) 2 . . 3 ? Cl1 Cl1A C50 Cl1B -173(7) . . . . ? C50 Cl1A C50 Cl1B -177(5) 2 . . . ? Cl1B Cl1A C50 Cl1 -44(4) . . . 3 ? Cl1 Cl1A C50 Cl1 143(4) . . . 3 ? C50 Cl1A C50 Cl1 139(3) 2 . . 3 ? Cl1B Cl1A C50 Cl1B -75(4) . . . 3 ? Cl1 Cl1A C50 Cl1B 112(4) . . . 3 ? C50 Cl1A C50 Cl1B 108(3) 2 . . 3 ? Cl1B Cl1A C50 Cl1 173(7) . . . . ? C50 Cl1A C50 Cl1 -4(4) 2 . . . ? Cl1B Cl1A C50 Cl1A -59(5) . . . 3 ? Cl1 Cl1A C50 Cl1A 128(3) . . . 3 ? C50 Cl1A C50 Cl1A 124(3) 2 . . 3 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.492 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.074