# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Antonio Papagni' _publ_contact_author_email antonio.papagni@mater.unimib.it _publ_section_title ; Novel fluorinated amino-stilbenes and their solid-state photodimerization ; loop_ _publ_author_name 'Antonio Papagni' 'Luciano Miozzo' 'P.Del Buttero' 'Chiara Bertarelli' 'Massimo Moret' ; S.Rizzato ; 'Mary Pryce' # Attachment '- compound_1.cif' data_MoretHnu _database_code_depnum_ccdc_archive 'CCDC 717576' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-2,3,4,5,6-pentafluoro-4'-dimethylamino-stilbene ; _chemical_name_common trans-2,3,4,5,6-pentafluoro-4'-dimethylamino-stilbene _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 F5 N' _chemical_formula_sum 'C16 H12 F5 N' _chemical_formula_weight 313.27 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 6.3683(4) _cell_length_b 30.029(2) _cell_length_c 7.2921(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.933(2) _cell_angle_gamma 90.00 _cell_volume 1387.01(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 5 _cell_measurement_theta_max 20 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.758 _exptl_absorpt_correction_T_max 0.99 _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 'area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11419 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2439 _reflns_number_gt 1416 _reflns_threshold_expression 'all reflections' _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^)+(0.0685P)^2^+1.2419P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2439 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.818 _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 F1 F 0.9906(3) 0.05177(6) 0.9142(3) 0.0741(6) Uani 1 1 d . . . F2 F 1.1003(3) 0.13772(6) 0.9357(3) 0.0851(6) Uani 1 1 d . . . F3 F 0.8209(3) 0.20181(6) 0.8109(3) 0.0914(7) Uani 1 1 d . . . F4 F 0.4265(3) 0.17807(6) 0.6681(3) 0.0884(7) Uani 1 1 d . . . F5 F 0.3112(3) 0.09326(6) 0.6459(3) 0.0709(5) Uani 1 1 d . . . N N 0.2136(4) -0.18263(9) 0.7094(4) 0.0780(9) Uani 1 1 d . . . C6 C 0.6481(3) 0.06947(4) 0.7812(3) 0.0496(7) Uani 1 1 d G . . C1 C 0.8504(3) 0.08137(6) 0.8547(3) 0.0561(8) Uani 1 1 d G . . C2 C 0.9088(2) 0.12597(6) 0.8645(3) 0.0592(8) Uani 1 1 d G . . C3 C 0.7649(3) 0.15868(5) 0.8010(3) 0.0636(9) Uani 1 1 d G . . C4 C 0.5625(3) 0.14679(5) 0.7275(3) 0.0619(8) Uani 1 1 d G . . C5 C 0.5041(2) 0.10219(6) 0.7176(3) 0.0542(7) Uani 1 1 d G . . C7 C 0.5958(5) 0.02107(10) 0.7785(4) 0.0564(8) Uani 1 1 d . . . H7 H 0.7045 0.0021 0.8237 0.068 Uiso 1 1 calc R . . C8 C 0.4149(5) 0.00157(10) 0.7202(4) 0.0577(8) Uani 1 1 d . . . H8 H 0.3053 0.0203 0.6747 0.069 Uiso 1 1 calc R . . C9 C 0.3673(3) -0.04712(4) 0.7194(3) 0.0520(7) Uani 1 1 d G . . C10 C 0.5208(2) -0.07865(6) 0.7745(3) 0.0551(8) Uani 1 1 d G . . H10 H 0.6577 -0.0696 0.8140 0.066 Uiso 1 1 calc R . . C11 C 0.4696(2) -0.12366(5) 0.7705(3) 0.0568(8) Uani 1 1 d G . . H11 H 0.5723 -0.1448 0.8074 0.068 Uiso 1 1 calc R . . C12 C 0.2649(3) -0.13715(4) 0.7115(3) 0.0515(7) Uani 1 1 d G . . C13 C 0.1114(2) -0.10561(6) 0.6564(3) 0.0568(8) Uani 1 1 d G . . H13 H -0.0255 -0.1146 0.6169 0.068 Uiso 1 1 calc R . . C14 C 0.1626(2) -0.06060(5) 0.6604(3) 0.0569(8) Uani 1 1 d G . . H14 H 0.0599 -0.0395 0.6235 0.068 Uiso 1 1 calc R . . C15 C 0.0013(5) -0.19733(12) 0.6573(6) 0.0881(12) Uani 1 1 d . . . H151 H -0.0041 -0.2292 0.6625 0.106 Uiso 1 1 calc R . . H152 H -0.0433 -0.1876 0.5340 0.106 Uiso 1 1 calc R . . H153 H -0.0906 -0.1850 0.7405 0.106 Uiso 1 1 calc R . . C16 C 0.3732(6) -0.21576(11) 0.7473(6) 0.0909(12) Uani 1 1 d . . . H161 H 0.3099 -0.2448 0.7379 0.109 Uiso 1 1 calc R . . H162 H 0.4415 -0.2115 0.8697 0.109 Uiso 1 1 calc R . . H163 H 0.4754 -0.2132 0.6599 0.109 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 F1 0.0578(11) 0.0703(12) 0.0915(14) -0.0002(10) -0.0053(10) 0.0124(9) F2 0.0635(12) 0.0902(14) 0.0995(15) -0.0172(11) -0.0023(11) -0.0171(10) F3 0.1026(16) 0.0561(12) 0.1156(17) -0.0029(11) 0.0107(13) -0.0169(11) F4 0.0901(15) 0.0625(12) 0.1092(16) 0.0181(11) -0.0065(12) 0.0143(10) F5 0.0577(11) 0.0687(12) 0.0826(13) 0.0065(9) -0.0105(9) 0.0017(9) N 0.0584(17) 0.0534(17) 0.120(3) -0.0027(16) 0.0007(16) -0.0007(13) C6 0.0517(17) 0.0556(18) 0.0419(16) -0.0006(13) 0.0062(13) 0.0012(14) C1 0.0549(18) 0.065(2) 0.0488(18) -0.0009(14) 0.0066(14) 0.0042(15) C2 0.0532(19) 0.068(2) 0.0556(19) -0.0084(16) 0.0041(14) -0.0109(16) C3 0.076(2) 0.054(2) 0.062(2) -0.0017(16) 0.0107(17) -0.0099(17) C4 0.069(2) 0.058(2) 0.059(2) 0.0086(15) 0.0063(16) 0.0066(17) C5 0.0551(19) 0.0602(19) 0.0469(17) 0.0033(14) 0.0028(14) 0.0006(15) C7 0.0572(18) 0.0581(19) 0.0531(18) 0.0004(14) 0.0016(14) 0.0030(15) C8 0.0581(19) 0.0567(19) 0.0574(18) 0.0018(15) 0.0009(15) 0.0035(15) C9 0.0550(18) 0.0544(18) 0.0466(16) 0.0013(13) 0.0061(13) 0.0033(14) C10 0.0438(16) 0.064(2) 0.0565(18) -0.0040(15) 0.0011(13) -0.0025(14) C11 0.0501(18) 0.0548(19) 0.064(2) -0.0012(15) -0.0002(14) 0.0079(14) C12 0.0509(17) 0.0504(17) 0.0527(18) -0.0015(13) 0.0029(14) 0.0012(13) C13 0.0452(16) 0.064(2) 0.0590(19) -0.0009(15) -0.0039(14) -0.0022(14) C14 0.0537(18) 0.0581(19) 0.0572(19) 0.0043(14) -0.0022(14) 0.0064(14) C15 0.078(3) 0.063(2) 0.120(3) -0.018(2) -0.001(2) -0.0138(19) C16 0.088(3) 0.053(2) 0.131(4) 0.010(2) 0.009(2) 0.0066(19) _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 F1 C1 1.302(2) . ? F2 C2 1.323(2) . ? F3 C3 1.343(2) . ? F4 C4 1.320(2) . ? F5 C5 1.312(2) . ? N C12 1.404(3) . ? N C16 1.429(4) . ? N C15 1.435(4) . ? C6 C1 1.3900 . ? C6 C5 1.3900 . ? C6 C7 1.491(3) . ? C1 C2 1.3900 . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C7 C8 1.322(4) . ? C7 H7 0.9300 . ? C8 C9 1.493(3) . ? C8 H8 0.9300 . ? C9 C10 1.3900 . ? C9 C14 1.3900 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H151 0.9600 . ? C15 H152 0.9600 . ? C15 H153 0.9600 . ? C16 H161 0.9600 . ? C16 H162 0.9600 . ? C16 H163 0.9600 . ? 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 C12 N C16 121.0(3) . . ? C12 N C15 120.9(3) . . ? C16 N C15 118.0(3) . . ? C1 C6 C5 120.0 . . ? C1 C6 C7 116.90(17) . . ? C5 C6 C7 123.09(17) . . ? F1 C1 C6 121.97(16) . . ? F1 C1 C2 118.02(16) . . ? C6 C1 C2 120.0 . . ? F2 C2 C1 120.55(16) . . ? F2 C2 C3 119.45(17) . . ? C1 C2 C3 120.0 . . ? F3 C3 C4 119.93(17) . . ? F3 C3 C2 120.07(17) . . ? C4 C3 C2 120.0 . . ? F4 C4 C3 119.64(16) . . ? F4 C4 C5 120.36(16) . . ? C3 C4 C5 120.0 . . ? F5 C5 C4 116.88(15) . . ? F5 C5 C6 123.12(15) . . ? C4 C5 C6 120.0 . . ? C8 C7 C6 128.4(3) . . ? C8 C7 H7 115.8 . . ? C6 C7 H7 115.8 . . ? C7 C8 C9 127.2(3) . . ? C7 C8 H8 116.4 . . ? C9 C8 H8 116.4 . . ? C10 C9 C14 120.0 . . ? C10 C9 C8 121.96(16) . . ? C14 C9 C8 118.04(16) . . ? C9 C10 C11 120.0 . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 N 120.22(17) . . ? C11 C12 N 119.78(17) . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 120.0 . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? N C15 H151 109.5 . . ? N C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? N C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? N C16 H161 109.5 . . ? N C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? N C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.323 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.040