# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # 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_06191m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H26 F2 N2, C H Cl3' _chemical_formula_sum 'C38 H27 Cl3 F2 N2' _chemical_formula_weight 655.97 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' F F 0.0171 0.0103 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3685(4) _cell_length_b 12.2751(6) _cell_length_c 14.8984(7) _cell_angle_alpha 79.5560(10) _cell_angle_beta 74.4570(10) _cell_angle_gamma 80.6210(10) _cell_volume 1611.43(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6624 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.06 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8724 _exptl_absorpt_correction_T_max 0.9346 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 AXS SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12410 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.99 _reflns_number_total 6164 _reflns_number_gt 4825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT-PLUS (Bruker, 2003)' _computing_data_reduction SAINT-PLUS _computing_structure_solution 'SHELXTL (Bruker, 2005)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0848P)^2^+1.4406P] 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 6164 _refine_ls_number_parameters 418 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1664 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1835(2) 0.92229(19) 0.73324(16) 0.0241(5) Uani 1 1 d . . . C2 C 1.1496(3) 0.8514(2) 0.68092(17) 0.0284(5) Uani 1 1 d . . . H2 H 1.2272 0.8157 0.6365 0.034 Uiso 1 1 calc R . . C3 C 1.0039(3) 0.8327(2) 0.69330(17) 0.0270(5) Uani 1 1 d . . . H3 H 0.9829 0.7842 0.6567 0.032 Uiso 1 1 calc R . . C4 C 0.8869(2) 0.88269(18) 0.75765(15) 0.0215(4) Uani 1 1 d . . . C5 C 0.9229(3) 0.95120(19) 0.81138(16) 0.0240(5) Uani 1 1 d . . . H5 H 0.8457 0.9850 0.8572 0.029 Uiso 1 1 calc R . . C6 C 1.0680(3) 0.97102(19) 0.79945(16) 0.0251(5) Uani 1 1 d . . . H6 H 1.0893 1.0184 0.8368 0.030 Uiso 1 1 calc R . . C7 C 0.7271(2) 0.85792(18) 0.77172(15) 0.0215(5) Uani 1 1 d . . . C8 C 0.6972(2) 0.84122(18) 0.67887(16) 0.0223(5) Uani 1 1 d . . . C9 C 0.7263(3) 0.9244(2) 0.60036(16) 0.0273(5) Uani 1 1 d . . . H9 H 0.7714 0.9865 0.6049 0.033 Uiso 1 1 calc R . . C10 C 0.6921(3) 0.9192(2) 0.51729(17) 0.0330(6) Uani 1 1 d . . . H10 H 0.7122 0.9779 0.4662 0.040 Uiso 1 1 calc R . . C11 C 0.6277(3) 0.8283(2) 0.50699(18) 0.0348(6) Uani 1 1 d . . . C12 C 0.6005(3) 0.7443(2) 0.58385(19) 0.0347(6) Uani 1 1 d . . . H12 H 0.5581 0.6811 0.5788 0.042 Uiso 1 1 calc R . . C13 C 0.6344(3) 0.7511(2) 0.66765(17) 0.0280(5) Uani 1 1 d . . . H13 H 0.6140 0.6926 0.7188 0.034 Uiso 1 1 calc R . . C14 C 0.6931(2) 0.75796(19) 0.84932(15) 0.0222(5) Uani 1 1 d . . . C15 C 0.7699(3) 0.65150(19) 0.85640(16) 0.0250(5) Uani 1 1 d . . . H15 H 0.8549 0.6318 0.8082 0.030 Uiso 1 1 calc R . . C16 C 0.7210(3) 0.57305(19) 0.93546(16) 0.0263(5) Uani 1 1 d . . . C17 C 0.7957(3) 0.4568(2) 0.94420(17) 0.0284(5) Uani 1 1 d . . . C18 C 0.8322(3) 0.3969(2) 0.86856(17) 0.0301(5) Uani 1 1 d . . . H18 H 0.8155 0.4329 0.8096 0.036 Uiso 1 1 calc R . . C19 C 0.8926(3) 0.2853(2) 0.87759(18) 0.0332(6) Uani 1 1 d . . . H19 H 0.9156 0.2444 0.8261 0.040 Uiso 1 1 calc R . . C20 C 0.9180(3) 0.2359(2) 0.96362(19) 0.0336(6) Uani 1 1 d . . . C21 C 0.8856(3) 0.2919(2) 1.0400(2) 0.0410(6) Uani 1 1 d . . . H21 H 0.9051 0.2558 1.0983 0.049 Uiso 1 1 calc R . . C22 C 0.8237(3) 0.4024(2) 1.02960(19) 0.0384(6) Uani 1 1 d . . . H22 H 0.7998 0.4422 1.0818 0.046 Uiso 1 1 calc R . . C23 C 0.5969(3) 0.6043(2) 1.00614(17) 0.0288(5) Uani 1 1 d . . . H23 H 0.5655 0.5517 1.0605 0.035 Uiso 1 1 calc R . . C24 C 0.5190(3) 0.70983(19) 0.99880(16) 0.0268(5) Uani 1 1 d . . . H24 H 0.4335 0.7295 1.0467 0.032 Uiso 1 1 calc R . . C25 C 0.5682(2) 0.78674(19) 0.91983(16) 0.0230(5) Uani 1 1 d . . . C26 C 0.5128(2) 0.90383(19) 0.89640(15) 0.0227(5) Uani 1 1 d . . . C27 C 0.3895(3) 0.9695(2) 0.94226(16) 0.0257(5) Uani 1 1 d . . . H27 H 0.3231 0.9380 0.9975 0.031 Uiso 1 1 calc R . . C28 C 0.3639(3) 1.0815(2) 0.90695(17) 0.0263(5) Uani 1 1 d . . . H28 H 0.2799 1.1267 0.9386 0.032 Uiso 1 1 calc R . . C29 C 0.4605(2) 1.12907(19) 0.82503(16) 0.0237(5) Uani 1 1 d . . . C30 C 0.4302(3) 1.24904(19) 0.78788(16) 0.0258(5) Uani 1 1 d . . . C31 C 0.2845(3) 1.3008(2) 0.79717(19) 0.0326(6) Uani 1 1 d . . . H31 H 0.2042 1.2583 0.8275 0.039 Uiso 1 1 calc R . . C32 C 0.2532(3) 1.4120(2) 0.7637(2) 0.0401(6) Uani 1 1 d . . . H32 H 0.1530 1.4460 0.7705 0.048 Uiso 1 1 calc R . . C33 C 0.3701(3) 1.4723(2) 0.7202(2) 0.0462(7) Uani 1 1 d . . . C34 C 0.5163(3) 1.4252(2) 0.7086(2) 0.0466(7) Uani 1 1 d . . . H34 H 0.5956 1.4686 0.6779 0.056 Uiso 1 1 calc R . . C35 C 0.5457(3) 1.3134(2) 0.7424(2) 0.0349(6) Uani 1 1 d . . . H35 H 0.6462 1.2799 0.7346 0.042 Uiso 1 1 calc R . . C36 C 0.5833(2) 1.06164(19) 0.77884(16) 0.0230(5) Uani 1 1 d . . . H36 H 0.6499 1.0928 0.7235 0.028 Uiso 1 1 calc R . . C37 C 0.6080(2) 0.94931(18) 0.81361(15) 0.0216(5) Uani 1 1 d . . . F1 F 0.9765(2) 0.12675(13) 0.97287(12) 0.0471(4) Uani 1 1 d . . . F2 F 0.3394(2) 1.58187(15) 0.68732(19) 0.0759(7) Uani 1 1 d . . . N1 N 1.3284(2) 0.9495(2) 0.71646(16) 0.0322(5) Uani 1 1 d . . . H1A H 1.345(4) 0.970(3) 0.765(2) 0.048 Uiso 1 1 d . . . H1B H 1.399(4) 0.898(3) 0.687(2) 0.048 Uiso 1 1 d . . . N2 N 0.5930(4) 0.8237(3) 0.4235(2) 0.0618(9) Uani 1 1 d . . . H2A H 0.613(5) 0.875(4) 0.382(4) 0.093 Uiso 1 1 d . . . H2B H 0.568(5) 0.766(4) 0.415(3) 0.093 Uiso 1 1 d . . . C38 C 0.0100(4) 0.7145(3) 0.4506(2) 0.0523(8) Uani 1 1 d . . . H38 H -0.0793 0.7322 0.5025 0.063 Uiso 1 1 calc R . . Cl1 Cl 0.16369(11) 0.66800(9) 0.49913(7) 0.0673(3) Uani 1 1 d . . . Cl2 Cl 0.03776(10) 0.83456(7) 0.36781(7) 0.0643(3) Uani 1 1 d . . . Cl3 Cl -0.0255(2) 0.61011(11) 0.39779(10) 0.1204(6) Uani 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 0.0215(11) 0.0269(12) 0.0243(11) 0.0022(9) -0.0091(9) -0.0049(9) C2 0.0208(11) 0.0347(13) 0.0288(12) -0.0101(10) -0.0026(9) -0.0004(9) C3 0.0230(11) 0.0298(12) 0.0311(12) -0.0122(10) -0.0060(10) -0.0037(9) C4 0.0202(11) 0.0212(11) 0.0226(11) -0.0005(8) -0.0053(9) -0.0039(8) C5 0.0231(11) 0.0266(11) 0.0217(11) -0.0040(9) -0.0041(9) -0.0026(9) C6 0.0243(11) 0.0286(12) 0.0261(11) -0.0068(9) -0.0097(9) -0.0046(9) C7 0.0185(11) 0.0223(11) 0.0237(11) -0.0037(9) -0.0045(8) -0.0034(8) C8 0.0175(10) 0.0251(11) 0.0237(11) -0.0056(9) -0.0036(8) -0.0010(8) C9 0.0279(12) 0.0280(12) 0.0261(12) -0.0042(9) -0.0045(9) -0.0071(9) C10 0.0413(15) 0.0326(13) 0.0248(12) -0.0003(10) -0.0081(11) -0.0074(11) C11 0.0403(15) 0.0411(15) 0.0270(12) -0.0062(11) -0.0119(11) -0.0086(11) C12 0.0393(14) 0.0349(14) 0.0350(14) -0.0080(11) -0.0102(11) -0.0142(11) C13 0.0280(12) 0.0285(12) 0.0277(12) -0.0021(9) -0.0054(10) -0.0085(9) C14 0.0227(11) 0.0255(11) 0.0204(10) -0.0032(9) -0.0062(9) -0.0068(9) C15 0.0239(11) 0.0260(12) 0.0249(11) -0.0047(9) -0.0043(9) -0.0038(9) C16 0.0296(12) 0.0248(12) 0.0265(12) -0.0037(9) -0.0093(10) -0.0048(9) C17 0.0292(12) 0.0258(12) 0.0279(12) 0.0000(9) -0.0041(10) -0.0058(9) C18 0.0285(12) 0.0332(13) 0.0276(12) -0.0034(10) -0.0058(10) -0.0033(10) C19 0.0298(13) 0.0327(13) 0.0355(14) -0.0115(11) -0.0025(11) -0.0015(10) C20 0.0324(13) 0.0227(12) 0.0390(14) -0.0011(10) -0.0026(11) 0.0016(10) C21 0.0542(17) 0.0320(14) 0.0322(14) 0.0010(11) -0.0111(12) 0.0030(12) C22 0.0536(17) 0.0315(14) 0.0288(13) -0.0054(11) -0.0109(12) 0.0005(12) C23 0.0348(13) 0.0274(12) 0.0239(12) -0.0007(9) -0.0050(10) -0.0096(10) C24 0.0276(12) 0.0286(12) 0.0231(11) -0.0041(9) -0.0024(9) -0.0064(9) C25 0.0209(11) 0.0260(11) 0.0251(11) -0.0063(9) -0.0073(9) -0.0056(9) C26 0.0203(11) 0.0275(12) 0.0222(11) -0.0049(9) -0.0062(9) -0.0053(9) C27 0.0223(11) 0.0328(13) 0.0221(11) -0.0054(9) -0.0027(9) -0.0060(9) C28 0.0205(11) 0.0308(12) 0.0286(12) -0.0109(10) -0.0052(9) -0.0001(9) C29 0.0206(11) 0.0265(12) 0.0275(12) -0.0074(9) -0.0094(9) -0.0034(9) C30 0.0257(12) 0.0275(12) 0.0263(11) -0.0085(9) -0.0078(9) -0.0017(9) C31 0.0263(12) 0.0306(13) 0.0406(14) -0.0063(11) -0.0079(11) -0.0018(10) C32 0.0320(14) 0.0353(14) 0.0506(17) -0.0059(12) -0.0124(12) 0.0059(11) C33 0.0468(17) 0.0247(13) 0.0604(19) 0.0024(12) -0.0116(14) 0.0021(12) C34 0.0386(16) 0.0314(15) 0.062(2) 0.0039(13) -0.0044(14) -0.0073(12) C35 0.0262(13) 0.0314(13) 0.0439(15) -0.0030(11) -0.0055(11) -0.0022(10) C36 0.0196(11) 0.0256(11) 0.0241(11) -0.0034(9) -0.0043(9) -0.0049(9) C37 0.0182(10) 0.0257(11) 0.0233(11) -0.0061(9) -0.0064(9) -0.0043(8) F1 0.0560(10) 0.0290(8) 0.0469(10) -0.0056(7) -0.0054(8) 0.0100(7) F2 0.0562(12) 0.0322(10) 0.1178(19) 0.0184(11) -0.0100(12) 0.0041(8) N1 0.0200(10) 0.0466(13) 0.0328(12) -0.0089(10) -0.0079(9) -0.0063(9) N2 0.105(3) 0.0587(19) 0.0360(14) -0.0004(13) -0.0335(16) -0.0315(18) C38 0.056(2) 0.0558(19) 0.0438(17) 0.0012(14) -0.0123(15) -0.0135(15) Cl1 0.0622(6) 0.0811(7) 0.0606(5) -0.0264(5) -0.0215(4) 0.0142(5) Cl2 0.0600(5) 0.0514(5) 0.0637(5) 0.0066(4) 0.0052(4) -0.0065(4) Cl3 0.2242(18) 0.0833(8) 0.0917(9) 0.0137(7) -0.0864(11) -0.0767(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 C6 1.390(3) . ? C1 C2 1.391(3) . ? C1 N1 1.397(3) . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 C7 1.528(3) . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C14 1.536(3) . ? C7 C8 1.537(3) . ? C7 C37 1.538(3) . ? C8 C13 1.389(3) . ? C8 C9 1.404(3) . ? C9 C10 1.374(3) . ? C9 H9 0.9500 . ? C10 C11 1.401(4) . ? C10 H10 0.9500 . ? C11 N2 1.380(4) . ? C11 C12 1.393(4) . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 C25 1.392(3) . ? C15 C16 1.403(3) . ? C15 H15 0.9500 . ? C16 C23 1.397(3) . ? C16 C17 1.483(3) . ? C17 C18 1.393(3) . ? C17 C22 1.396(4) . ? C18 C19 1.391(4) . ? C18 H18 0.9500 . ? C19 C20 1.379(4) . ? C19 H19 0.9500 . ? C20 F1 1.360(3) . ? C20 C21 1.375(4) . ? C21 C22 1.384(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.381(3) . ? C23 H23 0.9500 . ? C24 C25 1.392(3) . ? C24 H24 0.9500 . ? C25 C26 1.459(3) . ? C26 C27 1.387(3) . ? C26 C37 1.397(3) . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 C29 1.404(3) . ? C28 H28 0.9500 . ? C29 C36 1.398(3) . ? C29 C30 1.486(3) . ? C30 C31 1.391(3) . ? C30 C35 1.394(4) . ? C31 C32 1.377(4) . ? C31 H31 0.9500 . ? C32 C33 1.371(4) . ? C32 H32 0.9500 . ? C33 F2 1.357(3) . ? C33 C34 1.376(4) . ? C34 C35 1.383(4) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.387(3) . ? C36 H36 0.9500 . ? N1 H1A 0.86(4) . ? N1 H1B 0.92(4) . ? N2 H2A 0.81(5) . ? N2 H2B 0.82(5) . ? C38 Cl3 1.736(4) . ? C38 Cl2 1.748(3) . ? C38 Cl1 1.750(4) . ? C38 H38 1.0000 . ? 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 C6 C1 C2 118.5(2) . . ? C6 C1 N1 120.2(2) . . ? C2 C1 N1 121.2(2) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 121.9(2) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 117.2(2) . . ? C3 C4 C7 120.72(19) . . ? C5 C4 C7 122.00(19) . . ? C6 C5 C4 121.5(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C4 C7 C14 110.33(17) . . ? C4 C7 C8 111.55(18) . . ? C14 C7 C8 112.30(17) . . ? C4 C7 C37 113.50(18) . . ? C14 C7 C37 100.67(17) . . ? C8 C7 C37 108.04(17) . . ? C13 C8 C9 116.3(2) . . ? C13 C8 C7 124.4(2) . . ? C9 C8 C7 119.13(19) . . ? C10 C9 C8 122.4(2) . . ? C10 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? C9 C10 C11 120.8(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? N2 C11 C12 122.0(3) . . ? N2 C11 C10 120.6(3) . . ? C12 C11 C10 117.4(2) . . ? C13 C12 C11 121.2(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 121.9(2) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 119.1 . . ? C15 C14 C25 120.3(2) . . ? C15 C14 C7 128.9(2) . . ? C25 C14 C7 110.74(19) . . ? C14 C15 C16 119.4(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C23 C16 C15 119.3(2) . . ? C23 C16 C17 119.4(2) . . ? C15 C16 C17 121.3(2) . . ? C18 C17 C22 118.2(2) . . ? C18 C17 C16 120.7(2) . . ? C22 C17 C16 121.1(2) . . ? C19 C18 C17 121.4(2) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C20 C19 C18 117.9(2) . . ? C20 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? F1 C20 C21 119.0(2) . . ? F1 C20 C19 118.1(2) . . ? C21 C20 C19 122.9(2) . . ? C20 C21 C22 118.1(2) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? C21 C22 C17 121.6(2) . . ? C21 C22 H22 119.2 . . ? C17 C22 H22 119.2 . . ? C24 C23 C16 121.5(2) . . ? C24 C23 H23 119.3 . . ? C16 C23 H23 119.3 . . ? C23 C24 C25 118.7(2) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C24 C25 C14 120.8(2) . . ? C24 C25 C26 130.2(2) . . ? C14 C25 C26 108.93(19) . . ? C27 C26 C37 120.3(2) . . ? C27 C26 C25 130.8(2) . . ? C37 C26 C25 108.98(19) . . ? C28 C27 C26 119.5(2) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C27 C28 C29 120.8(2) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C36 C29 C28 119.0(2) . . ? C36 C29 C30 121.0(2) . . ? C28 C29 C30 120.0(2) . . ? C31 C30 C35 117.7(2) . . ? C31 C30 C29 120.7(2) . . ? C35 C30 C29 121.6(2) . . ? C32 C31 C30 121.9(2) . . ? C32 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? C33 C32 C31 118.4(2) . . ? C33 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? F2 C33 C32 118.5(3) . . ? F2 C33 C34 119.4(3) . . ? C32 C33 C34 122.1(3) . . ? C33 C34 C35 118.7(3) . . ? C33 C34 H34 120.7 . . ? C35 C34 H34 120.7 . . ? C34 C35 C30 121.2(2) . . ? C34 C35 H35 119.4 . . ? C30 C35 H35 119.4 . . ? C37 C36 C29 120.1(2) . . ? C37 C36 H36 119.9 . . ? C29 C36 H36 119.9 . . ? C36 C37 C26 120.2(2) . . ? C36 C37 C7 129.4(2) . . ? C26 C37 C7 110.34(19) . . ? C1 N1 H1A 112(2) . . ? C1 N1 H1B 112(2) . . ? H1A N1 H1B 117(3) . . ? C11 N2 H2A 117(4) . . ? C11 N2 H2B 119(3) . . ? H2A N2 H2B 123(5) . . ? Cl3 C38 Cl2 109.39(18) . . ? Cl3 C38 Cl1 110.0(2) . . ? Cl2 C38 Cl1 111.89(19) . . ? Cl3 C38 H38 108.5 . . ? Cl2 C38 H38 108.5 . . ? Cl1 C38 H38 108.5 . . ? 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 C6 C1 C2 C3 1.6(3) . . . . ? N1 C1 C2 C3 -174.7(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C2 C3 C4 C7 -178.3(2) . . . . ? C3 C4 C5 C6 1.7(3) . . . . ? C7 C4 C5 C6 178.6(2) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? N1 C1 C6 C5 175.0(2) . . . . ? C3 C4 C7 C14 90.2(2) . . . . ? C5 C4 C7 C14 -86.5(2) . . . . ? C3 C4 C7 C8 -35.3(3) . . . . ? C5 C4 C7 C8 147.9(2) . . . . ? C3 C4 C7 C37 -157.6(2) . . . . ? C5 C4 C7 C37 25.6(3) . . . . ? C4 C7 C8 C13 129.8(2) . . . . ? C14 C7 C8 C13 5.3(3) . . . . ? C37 C7 C8 C13 -104.8(2) . . . . ? C4 C7 C8 C9 -54.1(3) . . . . ? C14 C7 C8 C9 -178.5(2) . . . . ? C37 C7 C8 C9 71.3(2) . . . . ? C13 C8 C9 C10 1.4(3) . . . . ? C7 C8 C9 C10 -175.0(2) . . . . ? C8 C9 C10 C11 -1.0(4) . . . . ? C9 C10 C11 N2 179.8(3) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? N2 C11 C12 C13 -179.1(3) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C11 C12 C13 C8 -0.3(4) . . . . ? C9 C8 C13 C12 -0.8(3) . . . . ? C7 C8 C13 C12 175.5(2) . . . . ? C4 C7 C14 C15 -54.7(3) . . . . ? C8 C7 C14 C15 70.5(3) . . . . ? C37 C7 C14 C15 -174.8(2) . . . . ? C4 C7 C14 C25 124.0(2) . . . . ? C8 C7 C14 C25 -110.9(2) . . . . ? C37 C7 C14 C25 3.8(2) . . . . ? C25 C14 C15 C16 -0.2(3) . . . . ? C7 C14 C15 C16 178.3(2) . . . . ? C14 C15 C16 C23 -0.8(3) . . . . ? C14 C15 C16 C17 177.4(2) . . . . ? C23 C16 C17 C18 132.7(3) . . . . ? C15 C16 C17 C18 -45.5(3) . . . . ? C23 C16 C17 C22 -43.7(3) . . . . ? C15 C16 C17 C22 138.1(3) . . . . ? C22 C17 C18 C19 1.1(4) . . . . ? C16 C17 C18 C19 -175.4(2) . . . . ? C17 C18 C19 C20 -1.2(4) . . . . ? C18 C19 C20 F1 179.7(2) . . . . ? C18 C19 C20 C21 0.4(4) . . . . ? F1 C20 C21 C22 -178.9(2) . . . . ? C19 C20 C21 C22 0.5(4) . . . . ? C20 C21 C22 C17 -0.6(4) . . . . ? C18 C17 C22 C21 -0.2(4) . . . . ? C16 C17 C22 C21 176.3(3) . . . . ? C15 C16 C23 C24 1.7(4) . . . . ? C17 C16 C23 C24 -176.6(2) . . . . ? C16 C23 C24 C25 -1.4(4) . . . . ? C23 C24 C25 C14 0.2(3) . . . . ? C23 C24 C25 C26 -176.5(2) . . . . ? C15 C14 C25 C24 0.6(3) . . . . ? C7 C14 C25 C24 -178.23(19) . . . . ? C15 C14 C25 C26 177.96(19) . . . . ? C7 C14 C25 C26 -0.8(2) . . . . ? C24 C25 C26 C27 -5.4(4) . . . . ? C14 C25 C26 C27 177.5(2) . . . . ? C24 C25 C26 C37 174.1(2) . . . . ? C14 C25 C26 C37 -3.0(2) . . . . ? C37 C26 C27 C28 -1.9(3) . . . . ? C25 C26 C27 C28 177.5(2) . . . . ? C26 C27 C28 C29 0.5(3) . . . . ? C27 C28 C29 C36 0.3(3) . . . . ? C27 C28 C29 C30 179.4(2) . . . . ? C36 C29 C30 C31 145.6(2) . . . . ? C28 C29 C30 C31 -33.5(3) . . . . ? C36 C29 C30 C35 -34.1(3) . . . . ? C28 C29 C30 C35 146.8(2) . . . . ? C35 C30 C31 C32 -0.4(4) . . . . ? C29 C30 C31 C32 179.8(2) . . . . ? C30 C31 C32 C33 -0.1(4) . . . . ? C31 C32 C33 F2 -179.8(3) . . . . ? C31 C32 C33 C34 0.5(5) . . . . ? F2 C33 C34 C35 180.0(3) . . . . ? C32 C33 C34 C35 -0.3(5) . . . . ? C33 C34 C35 C30 -0.2(5) . . . . ? C31 C30 C35 C34 0.6(4) . . . . ? C29 C30 C35 C34 -179.7(3) . . . . ? C28 C29 C36 C37 0.4(3) . . . . ? C30 C29 C36 C37 -178.7(2) . . . . ? C29 C36 C37 C26 -1.9(3) . . . . ? C29 C36 C37 C7 175.1(2) . . . . ? C27 C26 C37 C36 2.6(3) . . . . ? C25 C26 C37 C36 -176.89(19) . . . . ? C27 C26 C37 C7 -174.88(19) . . . . ? C25 C26 C37 C7 5.6(2) . . . . ? C4 C7 C37 C36 59.2(3) . . . . ? C14 C7 C37 C36 177.1(2) . . . . ? C8 C7 C37 C36 -65.0(3) . . . . ? C4 C7 C37 C26 -123.5(2) . . . . ? C14 C7 C37 C26 -5.7(2) . . . . ? C8 C7 C37 C26 112.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N1 0.81(5) 2.43(5) 3.222(4) 167(5) 2_776 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.794 _refine_diff_density_min -0.957 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 960578'