# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2009 data_global _journal_coden_Cambridge 171 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'William G. Skene' 'Andreanne Bolduc' 'Alex N. Bourque' 'Stephane Dufresne' 'Sergio Andres Perez Guarin' _publ_contact_author_name 'William G. Skene' _publ_contact_author_email W.SKENE@UMONTREAL.CA _publ_section_title ; Conjugated Fluorene-Thiophenes Prepared From Azomethines Connections-I: The Effect of Electronic and Aryl Groups on the Spectroscopic and Electrochemical Properties ; # Attachment 'SKENE8.CIF' data_skene8 _database_code_depnum_ccdc_archive 'CCDC 718758' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16 N2 S2' _chemical_formula_sum 'C23 H16 N2 S2' _chemical_formula_weight 384.50 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.0019(16) _cell_length_b 9.123(3) _cell_length_c 34.230(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1874.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.00 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.639 _exptl_absorpt_correction_Type gaussian _exptl_absorpt_correction_T_min 0.3600 _exptl_absorpt_correction_T_max 0.8200 _exptl_absorpt_process_details 'Gaussian from crystal shape' _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf-Nonius-CAD4 _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -0.13 _diffrn_reflns_number 20210 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 70.03 _reflns_number_total 3569 _reflns_number_gt 2971 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CAD4 Program (Nonius 1989)' _computing_cell_refinement 'CAD4 Program (Nonius 1989)' _computing_data_reduction 'Local Program' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0372P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs' _chemical_absolute_configuration rmad _refine_ls_abs_structure_Flack -0.001(17) _refine_ls_number_reflns 3569 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.928 _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 S1 S 0.34320(10) 0.04749(8) 1.14855(2) 0.0707(2) Uani 1 1 d . . . S2 S 0.28286(12) 1.06311(8) 0.77641(2) 0.0754(2) Uani 1 1 d . . . N1 N 0.2576(3) 0.27457(19) 1.08376(5) 0.0474(4) Uani 1 1 d . . . N2 N 0.2237(3) 0.8860(2) 0.85218(5) 0.0526(5) Uani 1 1 d . . . C1 C 0.5402(5) -0.0062(3) 1.18110(7) 0.0731(8) Uani 1 1 d . . . H1 H 0.5166 -0.0772 1.2002 0.088 Uiso 1 1 calc R . . C2 C 0.7351(4) 0.0657(3) 1.17619(7) 0.0679(7) Uani 1 1 d . . . H2 H 0.8606 0.0504 1.1916 0.082 Uiso 1 1 calc R . . C3 C 0.7262(4) 0.1652(3) 1.14539(7) 0.0575(6) Uani 1 1 d . . . H3 H 0.8463 0.2231 1.1379 0.069 Uiso 1 1 calc R . . C4 C 0.5237(3) 0.1692(2) 1.12738(6) 0.0473(5) Uani 1 1 d . . . C5 C 0.4575(4) 0.2615(2) 1.09528(6) 0.0496(5) Uani 1 1 d . . . H5 H 0.5673 0.3145 1.0823 0.060 Uiso 1 1 calc R . . C6 C 0.4722(6) 1.1701(4) 0.75275(9) 0.0862(9) Uani 1 1 d . . . H6 H 0.4400 1.2226 0.7301 0.103 Uiso 1 1 calc R . . C7 C 0.6725(5) 1.1709(4) 0.77008(9) 0.0848(9) Uani 1 1 d . . . H7 H 0.7938 1.2245 0.7610 0.102 Uiso 1 1 calc R . . C8 C 0.6782(5) 1.0817(3) 0.80338(7) 0.0696(7) Uani 1 1 d . . . H8 H 0.8046 1.0681 0.8187 0.084 Uiso 1 1 calc R . . C9 C 0.4764(4) 1.0167(3) 0.81095(6) 0.0558(6) Uani 1 1 d . . . C10 C 0.4201(4) 0.9277(3) 0.84426(6) 0.0551(6) Uani 1 1 d . . . H10 H 0.5345 0.8992 0.8609 0.066 Uiso 1 1 calc R . . C11 C 0.4295(3) 0.4941(2) 0.95089(6) 0.0481(5) Uani 1 1 d . . . H11A H 0.5786 0.5283 0.9569 0.058 Uiso 1 1 calc R . . H11B H 0.4397 0.4080 0.9343 0.058 Uiso 1 1 calc R . . C12 C 0.2939(3) 0.6126(2) 0.93166(6) 0.0431(5) Uani 1 1 d . . . C13 C 0.3388(3) 0.6908(2) 0.89824(6) 0.0474(5) Uani 1 1 d . . . H13 H 0.4675 0.6720 0.8840 0.057 Uiso 1 1 calc R . . C14 C 0.1896(4) 0.7988(2) 0.88587(6) 0.0461(5) Uani 1 1 d . . . C15 C -0.0059(3) 0.8233(2) 0.90732(6) 0.0498(5) Uani 1 1 d . . . H15 H -0.1076 0.8929 0.8986 0.060 Uiso 1 1 calc R . . C16 C -0.0506(3) 0.7462(2) 0.94110(7) 0.0472(5) Uani 1 1 d . . . H16 H -0.1795 0.7646 0.9553 0.057 Uiso 1 1 calc R . . C17 C 0.1007(3) 0.6404(2) 0.95349(6) 0.0412(5) Uani 1 1 d . . . C18 C 0.1038(3) 0.5469(2) 0.98836(6) 0.0416(4) Uani 1 1 d . . . C19 C -0.0401(3) 0.5356(2) 1.01993(6) 0.0470(5) Uani 1 1 d . . . H19 H -0.1720 0.5891 1.0205 0.056 Uiso 1 1 calc R . . C20 C 0.0148(3) 0.4439(2) 1.05056(6) 0.0469(5) Uani 1 1 d . . . H20 H -0.0818 0.4360 1.0717 0.056 Uiso 1 1 calc R . . C21 C 0.2131(3) 0.3626(2) 1.05052(6) 0.0438(5) Uani 1 1 d . . . C22 C 0.3545(3) 0.3699(2) 1.01811(6) 0.0453(5) Uani 1 1 d . . . H22 H 0.4835 0.3136 1.0172 0.054 Uiso 1 1 calc R . . C23 C 0.3004(3) 0.4617(2) 0.98758(6) 0.0426(4) 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 S1 0.0532(3) 0.0812(5) 0.0778(4) 0.0158(4) 0.0058(3) -0.0094(4) S2 0.0775(4) 0.0852(5) 0.0635(4) 0.0080(4) -0.0089(4) 0.0079(4) N1 0.0413(10) 0.0500(10) 0.0509(9) -0.0036(8) 0.0003(8) -0.0065(8) N2 0.0524(11) 0.0508(10) 0.0545(10) -0.0026(9) -0.0037(10) 0.0028(9) C1 0.0766(18) 0.086(2) 0.0572(14) 0.0189(14) 0.0091(14) 0.0115(16) C2 0.0669(16) 0.0809(18) 0.0561(14) -0.0055(14) -0.0097(13) 0.0080(16) C3 0.0473(12) 0.0642(14) 0.0609(13) -0.0039(12) -0.0063(12) -0.0037(12) C4 0.0427(11) 0.0488(12) 0.0504(11) -0.0070(10) 0.0046(10) -0.0020(10) C5 0.0404(11) 0.0514(13) 0.0570(13) -0.0027(11) 0.0018(10) -0.0101(10) C6 0.112(3) 0.081(2) 0.0664(16) 0.0174(16) 0.0220(18) 0.015(2) C7 0.084(2) 0.083(2) 0.088(2) 0.0040(18) 0.0285(19) -0.0005(19) C8 0.0652(16) 0.0787(18) 0.0650(15) 0.0001(14) 0.0082(14) -0.0005(15) C9 0.0584(14) 0.0586(14) 0.0503(12) -0.0063(11) 0.0026(11) 0.0052(12) C10 0.0553(13) 0.0601(14) 0.0501(12) -0.0037(12) -0.0059(11) 0.0045(12) C11 0.0398(10) 0.0516(12) 0.0530(12) -0.0063(10) 0.0023(10) 0.0102(9) C12 0.0373(10) 0.0401(10) 0.0519(11) -0.0094(9) 0.0007(10) 0.0047(9) C13 0.0397(11) 0.0496(12) 0.0528(12) -0.0066(10) 0.0042(10) 0.0052(10) C14 0.0444(11) 0.0440(11) 0.0498(11) -0.0074(9) -0.0040(10) 0.0022(9) C15 0.0400(11) 0.0456(12) 0.0638(14) -0.0058(11) -0.0069(11) 0.0063(10) C16 0.0336(10) 0.0467(11) 0.0614(13) -0.0095(11) -0.0008(10) 0.0034(9) C17 0.0340(10) 0.0369(10) 0.0527(12) -0.0095(9) -0.0022(9) 0.0003(8) C18 0.0328(9) 0.0391(10) 0.0531(11) -0.0108(10) -0.0036(9) -0.0006(9) C19 0.0294(9) 0.0500(12) 0.0616(13) -0.0102(11) 0.0026(9) -0.0011(9) C20 0.0347(10) 0.0515(12) 0.0546(11) -0.0074(11) 0.0043(9) -0.0072(10) C21 0.0370(10) 0.0424(10) 0.0519(11) -0.0076(10) -0.0017(10) -0.0070(9) C22 0.0350(10) 0.0458(11) 0.0550(12) -0.0090(10) -0.0009(10) 0.0029(9) C23 0.0347(9) 0.0427(10) 0.0505(11) -0.0101(9) 0.0013(9) 0.0012(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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 . . 1.697(3) Y S1 C4 . . 1.712(2) Y S2 C6 . . 1.703(3) Y S2 C9 . . 1.711(2) Y N1 C5 . . 1.268(3) Y N1 C21 . . 1.418(3) Y N2 C10 . . 1.268(3) Y N2 C14 . . 1.416(3) Y C1 C2 . . 1.352(4) Y C1 H1 . . 0.93 ? C2 C3 . . 1.392(3) Y C2 H2 . . 0.93 ? C3 C4 . . 1.364(3) Y C3 H3 . . 0.93 ? C4 C5 . . 1.441(3) Y C5 H5 . . 0.93 ? C6 C7 . . 1.341(4) Y C6 H6 . . 0.93 ? C7 C8 . . 1.401(4) Y C7 H7 . . 0.93 ? C8 C9 . . 1.373(3) Y C8 H8 . . 0.93 ? C9 C10 . . 1.440(3) Y C10 H10 . . 0.93 ? C11 C12 . . 1.505(3) Y C11 C23 . . 1.505(3) Y C11 H11a . . 0.97 ? C11 H11b . . 0.97 ? C12 C13 . . 1.374(3) Y C12 C17 . . 1.403(3) Y C13 C14 . . 1.397(3) Y C13 H13 . . 0.93 ? C14 C15 . . 1.402(3) Y C15 C16 . . 1.380(3) Y C15 H15 . . 0.93 ? C16 C17 . . 1.391(3) Y C16 H16 . . 0.93 ? C17 C18 . . 1.467(3) Y C18 C19 . . 1.387(3) Y C18 C23 . . 1.413(2) Y C19 C20 . . 1.381(3) Y C19 H19 . . 0.93 ? C20 C21 . . 1.402(3) Y C20 H20 . . 0.93 ? C21 C22 . . 1.399(3) Y C22 C23 . . 1.378(3) Y C22 H22 . . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 S1 C4 . . . 91.39(13) Y C6 S2 C9 . . . 91.00(16) Y C5 N1 C21 . . . 118.74(19) Y C10 N2 C14 . . . 118.5(2) Y C2 C1 S1 . . . 112.4(2) Y C2 C1 H1 . . . 123.8 ? S1 C1 H1 . . . 123.8 ? C1 C2 C3 . . . 112.2(2) Y C1 C2 H2 . . . 123.9 ? C3 C2 H2 . . . 123.9 ? C4 C3 C2 . . . 113.2(2) Y C4 C3 H3 . . . 123.4 ? C2 C3 H3 . . . 123.4 ? C3 C4 C5 . . . 127.3(2) Y C3 C4 S1 . . . 110.83(18) Y C5 C4 S1 . . . 121.85(17) Y N1 C5 C4 . . . 123.6(2) Y N1 C5 H5 . . . 118.2 ? C4 C5 H5 . . . 118.2 ? C7 C6 S2 . . . 113.0(2) Y C7 C6 H6 . . . 123.5 ? S2 C6 H6 . . . 123.5 ? C6 C7 C8 . . . 112.3(3) Y C6 C7 H7 . . . 123.9 ? C8 C7 H7 . . . 123.9 ? C9 C8 C7 . . . 112.5(3) Y C9 C8 H8 . . . 123.7 ? C7 C8 H8 . . . 123.7 ? C8 C9 C10 . . . 126.9(2) Y C8 C9 S2 . . . 111.19(19) Y C10 C9 S2 . . . 121.85(19) Y N2 C10 C9 . . . 123.8(2) Y N2 C10 H10 . . . 118.1 ? C9 C10 H10 . . . 118.1 ? C12 C11 C23 . . . 103.19(16) Y C12 C11 H11A . . . 111.1 ? C23 C11 H11A . . . 111.1 ? C12 C11 H11B . . . 111.1 ? C23 C11 H11B . . . 111.1 ? H11A C11 H11B . . . 109.1 ? C13 C12 C17 . . . 120.77(19) Y C13 C12 C11 . . . 129.12(18) Y C17 C12 C11 . . . 110.09(18) Y C12 C13 C14 . . . 119.51(19) Y C12 C13 H13 . . . 120.2 ? C14 C13 H13 . . . 120.2 ? C13 C14 C15 . . . 119.3(2) Y C13 C14 N2 . . . 123.4(2) Y C15 C14 N2 . . . 117.26(19) Y C16 C15 C14 . . . 121.3(2) Y C16 C15 H15 . . . 119.3 ? C14 C15 H15 . . . 119.3 ? C15 C16 C17 . . . 118.84(19) Y C15 C16 H16 . . . 120.6 ? C17 C16 H16 . . . 120.6 ? C16 C17 C12 . . . 120.2(2) Y C16 C17 C18 . . . 131.28(19) Y C12 C17 C18 . . . 108.53(17) Y C19 C18 C23 . . . 119.61(19) Y C19 C18 C17 . . . 131.96(18) Y C23 C18 C17 . . . 108.37(17) Y C20 C19 C18 . . . 119.16(19) Y C20 C19 H19 . . . 120.4 ? C18 C19 H19 . . . 120.4 ? C19 C20 C21 . . . 121.5(2) Y C19 C20 H20 . . . 119.2 ? C21 C20 H20 . . . 119.2 ? C22 C21 C20 . . . 119.3(2) Y C22 C21 N1 . . . 123.34(18) Y C20 C21 N1 . . . 117.31(19) Y C23 C22 C21 . . . 119.22(19) Y C23 C22 H22 . . . 120.4 ? C21 C22 H22 . . . 120.4 ? C22 C23 C18 . . . 121.10(19) Y C22 C23 C11 . . . 129.14(18) Y C18 C23 C11 . . . 109.72(18) Y 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C4 S1 C1 C2 . . . . 0.2(2) Y S1 C1 C2 C3 . . . . -0.5(3) Y C1 C2 C3 C4 . . . . 0.6(3) Y C2 C3 C4 C5 . . . . 178.6(2) Y C2 C3 C4 S1 . . . . -0.5(3) Y C1 S1 C4 C3 . . . . 0.16(19) Y C1 S1 C4 C5 . . . . -178.97(19) Y C21 N1 C5 C4 . . . . -176.66(19) Y C3 C4 C5 N1 . . . . -169.3(2) Y S1 C4 C5 N1 . . . . 9.7(3) Y C9 S2 C6 C7 . . . . 0.0(3) Y S2 C6 C7 C8 . . . . 0.7(4) Y C6 C7 C8 C9 . . . . -1.2(4) Y C7 C8 C9 C10 . . . . -175.1(2) Y C7 C8 C9 S2 . . . . 1.2(3) Y C6 S2 C9 C8 . . . . -0.7(2) Y C6 S2 C9 C10 . . . . 175.8(2) Y C14 N2 C10 C9 . . . . -179.93(19) Y C8 C9 C10 N2 . . . . 170.7(2) Y S2 C9 C10 N2 . . . . -5.2(3) Y C23 C11 C12 C13 . . . . 175.8(2) Y C23 C11 C12 C17 . . . . -3.1(2) Y C17 C12 C13 C14 . . . . -0.2(3) Y C11 C12 C13 C14 . . . . -179.0(2) Y C12 C13 C14 C15 . . . . -1.4(3) Y C12 C13 C14 N2 . . . . 179.07(19) Y C10 N2 C14 C13 . . . . -37.5(3) Y C10 N2 C14 C15 . . . . 142.9(2) Y C13 C14 C15 C16 . . . . 2.1(3) Y N2 C14 C15 C16 . . . . -178.33(19) Y C14 C15 C16 C17 . . . . -1.2(3) Y C15 C16 C17 C12 . . . . -0.5(3) Y C15 C16 C17 C18 . . . . 177.1(2) Y C13 C12 C17 C16 . . . . 1.2(3) Y C11 C12 C17 C16 . . . . -179.86(18) Y C13 C12 C17 C18 . . . . -176.91(18) Y C11 C12 C17 C18 . . . . 2.1(2) Y C16 C17 C18 C19 . . . . -0.9(4) Y C12 C17 C18 C19 . . . . 176.9(2) Y C16 C17 C18 C23 . . . . -177.9(2) Y C12 C17 C18 C23 . . . . -0.1(2) Y C23 C18 C19 C20 . . . . 1.7(3) Y C17 C18 C19 C20 . . . . -175.00(19) Y C18 C19 C20 C21 . . . . 0.3(3) Y C19 C20 C21 C22 . . . . -2.5(3) Y C19 C20 C21 N1 . . . . 178.35(18) Y C5 N1 C21 C22 . . . . 36.7(3) Y C5 N1 C21 C20 . . . . -144.1(2) Y C20 C21 C22 C23 . . . . 2.6(3) Y N1 C21 C22 C23 . . . . -178.24(18) Y C21 C22 C23 C18 . . . . -0.7(3) Y C21 C22 C23 C11 . . . . 176.7(2) Y C19 C18 C23 C22 . . . . -1.6(3) Y C17 C18 C23 C22 . . . . 175.89(18) Y C19 C18 C23 C11 . . . . -179.35(18) Y C17 C18 C23 C11 . . . . -1.9(2) Y C12 C11 C23 C22 . . . . -174.6(2) Y C12 C11 C23 C18 . . . . 3.0(2) Y _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.146 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.036