# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author 'MacGillivray, Leonard R.' _publ_contact_author_email len-macgillivray@uiowa.edu _publ_section_title ; Reversing the code of a template-directed solid-state synthesis: a bipyridine template that directs a single-crystal-to-single-crystal [2+2] photodimerisation of a dicarboxylic acid ; _publ_contact_author_name 'MacGillivray, Leonard R.' loop_ _publ_author_name T.Friscic L.R.MacGillivray data_2(2,3-4-pyr-nap).2(fum) _database_code_depnum_ccdc_archive 'CCDC 277440' _audit_creation_date 2005-07-08T13:13:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,3-bis(4-methylenethiopyridyl)naphthalene-fumaric acid 2/2 ; _chemical_formula_sum 'C26 H22 N2 O4 S2' _chemical_formula_weight 490.58 _chemical_formula_moiety 'C22 H18 N2 S2, C4 H4 O4' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 8.9652(9) _cell_length_b 14.3182(14) _cell_length_c 19.0890(19) _cell_angle_alpha 90 _cell_angle_beta 101.134(5) _cell_angle_gamma 90 _cell_volume 2404.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _space_group_name_H-M_alt P21/n #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_colour yellow _exptl_crystal_description prism _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_unetI/netI 0.0633 _diffrn_reflns_number 12524 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.07 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 4240 _reflns_number_gt 2379 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. All non-hydrogen atoms were included in the refinement following the anisotropic model. The coordinates of hydrogen atoms bonded to carbon atoms were calculated according to the hybridization of the belonging carbon atom. Hydrogen atoms of the hydroxylic groups were placed in positions that conformed to hybridization of the belonging oxygen atom as well as the maximum electron density surrounding the oxygen atom. ; _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^)+(0.1110P)^2^+0.0689P] 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 none _refine_ls_number_reflns 4240 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.2109 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.327 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.119 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.32282(11) 0.01738(8) 0.80570(5) 0.0762(4) Uani 1 1 d . . . S2 S 0.27511(12) -0.23343(9) 0.82430(6) 0.0820(4) Uani 1 1 d . . . O1 O 0.7343(3) 0.0824(3) 0.52861(15) 0.1093(12) Uani 1 1 d . . . H1O H 0.6918 0.0833 0.563 0.164 Uiso 1 1 calc R . . O2 O 0.9377(4) 0.1019(3) 0.61006(18) 0.1181(13) Uani 1 1 d . . . O3 O 1.3099(4) 0.1742(3) 0.45451(16) 0.1052(10) Uani 1 1 d . . . H3O H 1.3481 0.1882 0.4202 0.158 Uiso 1 1 calc R . . O4 O 1.1026(4) 0.1635(3) 0.3726(2) 0.1293(14) Uani 1 1 d . . . N1 N 0.5908(4) 0.0546(2) 0.62976(18) 0.0767(9) Uani 1 1 d . . . N2 N 0.5452(4) -0.2024(2) 0.64820(19) 0.0785(10) Uani 1 1 d . . . C1 C 0.6568(5) 0.0517(3) 0.6982(2) 0.0821(12) Uani 1 1 d . . . H1 H 0.7619 0.0572 0.7104 0.098 Uiso 1 1 calc R . . C2 C 0.5760(4) 0.0408(3) 0.7517(2) 0.0793(12) Uani 1 1 d . . . H2 H 0.6262 0.0398 0.7991 0.095 Uiso 1 1 calc R . . C3 C 0.4182(4) 0.0312(2) 0.7349(2) 0.0615(9) Uani 1 1 d . . . C4 C 0.3520(4) 0.0337(3) 0.6637(2) 0.0672(10) Uani 1 1 d . . . H4 H 0.2473 0.0274 0.6497 0.081 Uiso 1 1 calc R . . C5 C 0.4409(4) 0.0456(3) 0.6137(2) 0.0761(11) Uani 1 1 d . . . H5 H 0.3937 0.0475 0.5658 0.091 Uiso 1 1 calc R . . C6 C 0.1275(4) -0.0053(3) 0.7623(2) 0.0734(11) Uani 1 1 d . . . H6A H 0.0823 0.0512 0.7395 0.088 Uiso 1 1 calc R . . H6B H 0.1252 -0.0527 0.7258 0.088 Uiso 1 1 calc R . . C7 C 0.0379(4) -0.0382(3) 0.81711(19) 0.0661(10) Uani 1 1 d . . . C8 C -0.0249(4) 0.0266(3) 0.8556(2) 0.0723(11) Uani 1 1 d . . . H8 H -0.0084 0.0897 0.8482 0.087 Uiso 1 1 calc R . . C9 C -0.1137(4) 0.0010(3) 0.9058(2) 0.0714(11) Uani 1 1 d . . . C10 C -0.1781(5) 0.0678(4) 0.9451(2) 0.0967(14) Uani 1 1 d . . . H10 H -0.1581 0.1309 0.94 0.116 Uiso 1 1 calc R . . C11 C -0.2700(6) 0.0406(6) 0.9907(3) 0.116(2) Uani 1 1 d . . . H11 H -0.3129 0.0851 1.0163 0.14 Uiso 1 1 calc R . . C12 C -0.2992(6) -0.0533(6) 0.9990(3) 0.116(2) Uani 1 1 d . . . H12 H -0.3634 -0.0707 1.0297 0.139 Uiso 1 1 calc R . . C13 C -0.2368(5) -0.1208(4) 0.9636(2) 0.0936(14) Uani 1 1 d . . . H13 H -0.2565 -0.1835 0.9708 0.112 Uiso 1 1 calc R . . C14 C -0.1408(4) -0.0944(3) 0.9154(2) 0.0739(11) Uani 1 1 d . . . C15 C -0.0754(4) -0.1601(3) 0.8764(2) 0.0731(11) Uani 1 1 d . . . H15 H -0.0919 -0.2232 0.8836 0.088 Uiso 1 1 calc R . . C16 C 0.0121(4) -0.1355(3) 0.82796(19) 0.0640(10) Uani 1 1 d . . . C17 C 0.0748(4) -0.2114(3) 0.7871(2) 0.0791(12) Uani 1 1 d . . . H17A H 0.064 -0.193 0.7375 0.095 Uiso 1 1 calc R . . H17B H 0.0171 -0.2683 0.7889 0.095 Uiso 1 1 calc R . . C18 C 0.3708(4) -0.2240(3) 0.7528(2) 0.0654(10) Uani 1 1 d . . . C19 C 0.3053(5) -0.2242(3) 0.6818(2) 0.0759(11) Uani 1 1 d . . . H19 H 0.2009 -0.232 0.6673 0.091 Uiso 1 1 calc R . . C20 C 0.3973(5) -0.2125(3) 0.6322(2) 0.0855(13) Uani 1 1 d . . . H20 H 0.3511 -0.2119 0.5842 0.103 Uiso 1 1 calc R . . C21 C 0.6090(5) -0.2046(3) 0.7166(2) 0.0850(13) Uani 1 1 d . . . H21 H 0.7142 -0.1994 0.7289 0.102 Uiso 1 1 calc R . . C22 C 0.5294(4) -0.2142(3) 0.7704(2) 0.0821(12) Uani 1 1 d . . . H22 H 0.5794 -0.2143 0.8179 0.099 Uiso 1 1 calc R . . C26 C 1.1673(6) 0.1632(3) 0.4340(2) 0.0834(13) Uani 1 1 d . . . C25 C 1.0881(5) 0.1482(3) 0.4948(2) 0.0891(13) Uani 1 1 d . . . H25 H 1.1405 0.1623 0.5405 0.107 Uiso 1 1 calc R . . C24 C 0.9538(5) 0.1174(3) 0.4881(2) 0.0848(12) Uani 1 1 d . . . H24 H 0.9013 0.1044 0.4422 0.102 Uiso 1 1 calc R . . C23 C 0.8730(5) 0.1004(3) 0.5490(2) 0.0756(11) 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 0.0583(6) 0.1168(9) 0.0550(6) 0.0062(6) 0.0148(5) -0.0114(6) S2 0.0676(7) 0.1132(9) 0.0696(7) 0.0226(6) 0.0239(5) 0.0114(6) O1 0.065(2) 0.202(4) 0.0647(18) 0.008(2) 0.0209(16) -0.013(2) O2 0.078(2) 0.208(4) 0.072(2) -0.008(2) 0.0240(18) -0.040(2) O3 0.080(2) 0.166(3) 0.077(2) 0.012(2) 0.0326(18) -0.003(2) O4 0.074(2) 0.238(4) 0.078(2) 0.015(3) 0.0206(18) -0.018(2) N1 0.058(2) 0.107(3) 0.067(2) 0.0065(18) 0.0181(17) -0.0038(18) N2 0.066(2) 0.105(3) 0.070(2) 0.0025(19) 0.0248(19) 0.0054(19) C1 0.049(2) 0.115(3) 0.083(3) 0.015(3) 0.015(2) -0.002(2) C2 0.055(2) 0.120(3) 0.060(2) 0.017(2) 0.0034(19) -0.003(2) C3 0.053(2) 0.073(2) 0.060(2) 0.0108(18) 0.0135(18) -0.0025(18) C4 0.052(2) 0.089(3) 0.059(2) 0.002(2) 0.0081(18) -0.0105(19) C5 0.062(2) 0.114(3) 0.054(2) 0.003(2) 0.0135(19) -0.009(2) C6 0.057(2) 0.100(3) 0.064(2) 0.013(2) 0.0123(19) -0.008(2) C7 0.0425(19) 0.096(3) 0.059(2) 0.007(2) 0.0074(17) -0.0013(19) C8 0.057(2) 0.087(3) 0.072(3) 0.002(2) 0.010(2) -0.002(2) C9 0.047(2) 0.105(3) 0.061(2) -0.011(2) 0.0062(18) 0.006(2) C10 0.068(3) 0.137(4) 0.083(3) -0.023(3) 0.007(3) 0.008(3) C11 0.069(3) 0.194(7) 0.085(4) -0.040(4) 0.012(3) 0.019(4) C12 0.064(3) 0.226(7) 0.060(3) -0.016(4) 0.021(2) -0.006(4) C13 0.068(3) 0.152(4) 0.065(3) 0.001(3) 0.021(2) -0.014(3) C14 0.047(2) 0.118(4) 0.057(2) -0.002(2) 0.0107(18) -0.003(2) C15 0.060(2) 0.094(3) 0.067(2) 0.012(2) 0.017(2) -0.003(2) C16 0.0478(19) 0.088(3) 0.058(2) 0.001(2) 0.0133(17) 0.0012(19) C17 0.061(2) 0.096(3) 0.083(3) 0.005(2) 0.023(2) -0.003(2) C18 0.062(2) 0.071(2) 0.068(3) 0.0083(19) 0.023(2) 0.0056(18) C19 0.059(2) 0.103(3) 0.066(3) -0.004(2) 0.014(2) 0.003(2) C20 0.074(3) 0.123(4) 0.062(3) -0.005(2) 0.018(2) 0.013(3) C21 0.057(2) 0.118(4) 0.082(3) 0.002(3) 0.019(2) 0.000(2) C22 0.060(2) 0.123(3) 0.064(2) 0.010(2) 0.012(2) 0.002(2) C26 0.081(3) 0.117(4) 0.057(3) 0.004(2) 0.024(2) -0.011(3) C25 0.074(3) 0.123(4) 0.073(3) -0.011(3) 0.021(2) -0.009(3) C24 0.073(3) 0.108(3) 0.074(3) -0.002(2) 0.017(2) 0.001(3) C23 0.074(3) 0.100(3) 0.059(3) -0.002(2) 0.025(2) -0.011(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 C3 1.744(3) . ? S1 C6 1.816(4) . ? S2 C18 1.752(4) . ? S2 C17 1.826(4) . ? O1 C23 1.256(5) . ? O2 C23 1.198(5) . ? O3 C26 1.273(5) . ? O4 C26 1.202(5) . ? N1 C5 1.325(5) . ? N1 C1 1.327(5) . ? N2 C20 1.310(5) . ? N2 C21 1.321(5) . ? C1 C2 1.369(5) . ? C2 C3 1.395(5) . ? C3 C4 1.374(5) . ? C4 C5 1.368(5) . ? C6 C7 1.512(5) . ? C7 C8 1.370(5) . ? C7 C16 1.434(5) . ? C8 C9 1.408(5) . ? C9 C10 1.406(6) . ? C9 C14 1.406(6) . ? C10 C11 1.366(7) . ? C11 C12 1.385(8) . ? C12 C13 1.360(7) . ? C13 C14 1.428(5) . ? C14 C15 1.397(5) . ? C15 C16 1.369(5) . ? C16 C17 1.508(5) . ? C18 C19 1.369(5) . ? C18 C22 1.404(5) . ? C19 C20 1.380(5) . ? C21 C22 1.366(5) . ? C26 C25 1.489(5) . ? C25 C24 1.265(6) . ? C24 C23 1.504(5) . ? 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 C3 S1 C6 103.91(18) . . ? C18 S2 C17 106.03(19) . . ? C5 N1 C1 117.6(3) . . ? C20 N2 C21 116.9(3) . . ? N1 C1 C2 122.5(4) . . ? C1 C2 C3 120.0(4) . . ? C4 C3 C2 116.6(3) . . ? C4 C3 S1 125.9(3) . . ? C2 C3 S1 117.4(3) . . ? C5 C4 C3 119.7(3) . . ? N1 C5 C4 123.5(4) . . ? C7 C6 S1 109.5(3) . . ? C8 C7 C16 119.1(3) . . ? C8 C7 C6 119.2(4) . . ? C16 C7 C6 121.6(3) . . ? C7 C8 C9 122.3(4) . . ? C10 C9 C14 119.5(4) . . ? C10 C9 C8 122.0(5) . . ? C14 C9 C8 118.4(4) . . ? C11 C10 C9 120.4(5) . . ? C10 C11 C12 120.1(5) . . ? C13 C12 C11 121.8(5) . . ? C12 C13 C14 119.3(5) . . ? C15 C14 C9 119.0(3) . . ? C15 C14 C13 122.2(4) . . ? C9 C14 C13 118.8(4) . . ? C16 C15 C14 122.7(4) . . ? C15 C16 C7 118.5(3) . . ? C15 C16 C17 118.9(4) . . ? C7 C16 C17 122.6(3) . . ? C16 C17 S2 111.1(3) . . ? C19 C18 C22 117.3(3) . . ? C19 C18 S2 126.2(3) . . ? C22 C18 S2 116.5(3) . . ? C18 C19 C20 118.6(4) . . ? N2 C20 C19 124.5(4) . . ? N2 C21 C22 123.8(4) . . ? C21 C22 C18 118.8(4) . . ? O4 C26 O3 124.5(4) . . ? O4 C26 C25 123.2(4) . . ? O3 C26 C25 112.3(4) . . ? C24 C25 C26 123.9(5) . . ? C25 C24 C23 124.6(5) . . ? O2 C23 O1 124.8(4) . . ? O2 C23 C24 122.3(4) . . ? O1 C23 C24 112.9(4) . . ? _chemical_name_common '2,3-bis(4-methylenethiopyridyl)naphthalene-fumaric acid 2/2' data_2(2,3-4-pyr-nap).2(fum)_SCSC _database_code_depnum_ccdc_archive 'CCDC 277441' _audit_creation_date 2005-07-08T15:49:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,3-bis(4-methylenethiopyridyl)naphthalene-fumaric acid 2/2 36% SCSC ; _chemical_formula_sum 'C26 H22 N2 O4 S2' _chemical_formula_moiety 'C26 H22 N2 O4 S2' _chemical_formula_weight 490.58 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 9.0079(10) _cell_length_b 14.0545(15) _cell_length_c 18.9564(19) _cell_angle_alpha 90 _cell_angle_beta 101.564(5) _cell_angle_gamma 90 _cell_volume 2351.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_crystal_colour yellow _exptl_crystal_description prism _space_group_name_H-M_alt P21/n _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.1373 _diffrn_reflns_av_unetI/netI 0.1169 _diffrn_reflns_number 14873 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _reflns_number_total 4085 _reflns_number_gt 1769 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. All non-hydrogen atoms were refined according to the anisotropic model. Fumaric acid (fum) was found to be partially transformed in the photochemical dimer, rctt-1,2,3,4-cyclobutanetetracarboxylic acid (cbta). Consequently, fum abd cbta were refined as disordered over the same site, with occupational parameters of 0.64 for atoms of fum acid and 0.36 for atoms of cbta, except atoms C23, O1 and O2 that were common for both. During the refinement, carbon-oxygen bond lengths of the carboxylic acid moieties were constrained not to differ stringly from 1.21 A and 1.31 A, corresponding to a double and a single bond of the carboxylic acid group, respectively. Coordinates of hydrogen atoms bonded to carbon atoms were calculated according to the hybridization of the belonging carbon atom. Positions of hydrogen atoms of hydroxyl groups were generated following the stereochemical rules for the hybridization of the belonging oxygen atom, in the same time taking care to establish the best hydrogen bond to a neighbouring hydrogen bond-acceptor. ; _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^)+(0.0785P)^2^+3.6222P] 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 none _refine_ls_number_reflns 4085 _refine_ls_number_parameters 356 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.213 _refine_ls_R_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.2357 _refine_ls_wR_factor_gt 0.19 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.335 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.82512(17) 0.52751(16) 0.80913(9) 0.0782(7) Uani 1 1 d . . . S2 S 0.78443(19) 0.27264(17) 0.82537(10) 0.0854(7) Uani 1 1 d . . . O1 O 1.2264(6) 0.5820(6) 0.5288(3) 0.131(3) Uani 1 1 d D . . H1OA H 1.1902 0.567 0.5636 0.196 Uiso 1 1 calc R . . O2 O 1.4337(6) 0.6038(5) 0.6118(3) 0.106(2) Uani 1 1 d D . . N1 N 1.0914(6) 0.5609(5) 0.6323(3) 0.088(2) Uani 1 1 d . . . N2 N 1.0534(7) 0.3077(5) 0.6496(3) 0.0824(19) Uani 1 1 d . . . C5 C 0.9413(8) 0.5538(6) 0.6162(4) 0.085(2) Uani 1 1 d . . . H5 H 0.8936 0.5567 0.5679 0.102 Uiso 1 1 calc R . . C4 C 0.8521(7) 0.5426(5) 0.6668(4) 0.074(2) Uani 1 1 d . . . H4 H 0.7476 0.5365 0.6526 0.089 Uiso 1 1 calc R . . C3 C 0.9201(6) 0.5406(5) 0.7390(3) 0.0627(18) Uani 1 1 d . . . C2 C 1.0770(7) 0.5497(5) 0.7553(4) 0.071(2) Uani 1 1 d . . . H2 H 1.1284 0.5481 0.8031 0.086 Uiso 1 1 calc R . . C1 C 1.1555(7) 0.5609(5) 0.7014(4) 0.077(2) Uani 1 1 d . . . H1 H 1.2599 0.569 0.714 0.092 Uiso 1 1 calc R . . C6 C 0.6295(6) 0.5053(6) 0.7647(3) 0.076(2) Uani 1 1 d . . . H6A H 0.5842 0.5636 0.7429 0.091 Uiso 1 1 calc R . . H6B H 0.6266 0.4584 0.7269 0.091 Uiso 1 1 calc R . . C7 C 0.5413(6) 0.4698(6) 0.8187(3) 0.0613(18) Uani 1 1 d . . . C8 C 0.4764(7) 0.5322(6) 0.8579(4) 0.075(2) Uani 1 1 d . . . H8 H 0.4912 0.5969 0.8515 0.09 Uiso 1 1 calc R . . C9 C 0.3880(7) 0.5043(7) 0.9075(4) 0.073(2) Uani 1 1 d . . . C10 C 0.3183(8) 0.5717(7) 0.9461(4) 0.106(3) Uani 1 1 d . . . H10 H 0.3339 0.6365 0.9408 0.127 Uiso 1 1 calc R . . C11 C 0.2274(10) 0.5400(11) 0.9913(5) 0.130(5) Uani 1 1 d . . . H11 H 0.1829 0.5841 1.0172 0.156 Uiso 1 1 calc R . . C12 C 0.2009(10) 0.4449(12) 0.9992(5) 0.136(6) Uani 1 1 d . . . H12 H 0.1375 0.4255 1.0296 0.164 Uiso 1 1 calc R . . C13 C 0.2676(8) 0.3774(8) 0.9623(4) 0.100(3) Uani 1 1 d . . . H13 H 0.2495 0.313 0.968 0.12 Uiso 1 1 calc R . . C14 C 0.3631(7) 0.4069(8) 0.9159(3) 0.075(2) Uani 1 1 d . . . C15 C 0.4335(7) 0.3419(6) 0.8765(3) 0.070(2) Uani 1 1 d . . . H15 H 0.4203 0.277 0.8829 0.084 Uiso 1 1 calc R . . C16 C 0.5218(6) 0.3712(7) 0.8285(3) 0.066(2) Uani 1 1 d . . . C17 C 0.5855(7) 0.2960(6) 0.7865(4) 0.080(2) Uani 1 1 d . . . H17A H 0.5762 0.3167 0.7369 0.097 Uiso 1 1 calc R . . H17B H 0.5277 0.2377 0.7864 0.097 Uiso 1 1 calc R . . C18 C 0.8791(7) 0.2832(5) 0.7539(4) 0.0668(19) Uani 1 1 d . . . C22 C 1.0387(7) 0.2914(5) 0.7724(4) 0.072(2) Uani 1 1 d . . . H22 H 1.0888 0.289 0.8203 0.086 Uiso 1 1 calc R . . C21 C 1.1173(7) 0.3027(5) 0.7190(4) 0.073(2) Uani 1 1 d . . . H21 H 1.2223 0.3072 0.7317 0.088 Uiso 1 1 calc R . . C20 C 0.9034(8) 0.2973(6) 0.6326(4) 0.092(3) Uani 1 1 d . . . H20 H 0.8563 0.2982 0.5842 0.11 Uiso 1 1 calc R . . C19 C 0.8171(7) 0.2854(6) 0.6823(4) 0.082(2) Uani 1 1 d . . . H19 H 0.7128 0.2786 0.6673 0.098 Uiso 1 1 calc R . . C23 C 1.3696(6) 0.5985(6) 0.5497(3) 0.079(2) Uani 1 1 d D . . O3A O 1.8080(8) 0.6807(8) 0.4538(5) 0.081(3) Uani 0.64 1 d PD A 1 H3OA H 1.8489 0.6808 0.4189 0.121 Uiso 0.64 1 calc PR A 1 O4A O 1.6042(10) 0.6580(12) 0.3695(4) 0.094(4) Uani 0.64 1 d PD A 1 C24A C 1.4533(11) 0.6121(10) 0.4882(5) 0.063(4) Uani 0.64 1 d PD A 1 H24A H 1.4064 0.5913 0.4426 0.076 Uiso 0.64 1 calc PR A 1 C25A C 1.5873(12) 0.6512(9) 0.4957(5) 0.064(3) Uani 0.64 1 d PD A 1 H25A H 1.6365 0.6722 0.5409 0.076 Uiso 0.64 1 calc PR A 1 C26A C 1.6631(9) 0.6630(11) 0.4325(5) 0.061(4) Uani 0.64 1 d PD A 1 O3B O 1.7771(19) 0.611(2) 0.4479(10) 0.108(7) Uani 0.36 1 d PD B 2 H3OB H 1.7985 0.621 0.4085 0.162 Uiso 0.36 1 calc PR B 2 O4B O 1.556(2) 0.645(3) 0.3863(13) 0.127(10) Uani 0.36 1 d PD B 2 C24B C 1.403(2) 0.5486(16) 0.4860(17) 0.119(12) Uani 0.36 1 d PD . 2 H24B H 1.3468 0.5694 0.4388 0.142 Uiso 0.36 1 calc PR . 2 C25B C 1.575(2) 0.5623(13) 0.5017(12) 0.128(13) Uani 0.36 1 d PD . 2 H25B H 1.6084 0.5967 0.5471 0.153 Uiso 0.36 1 calc PR . 2 C26B C 1.630(2) 0.612(2) 0.4415(14) 0.110(14) Uani 0.36 1 d PD B 2 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 0.0489(10) 0.1291(19) 0.0570(11) 0.0025(11) 0.0115(8) -0.0078(10) S2 0.0547(11) 0.133(2) 0.0722(12) 0.0176(12) 0.0225(9) 0.0134(11) O1 0.077(4) 0.251(8) 0.066(3) 0.007(4) 0.019(3) -0.052(4) O2 0.079(3) 0.183(6) 0.057(3) -0.018(4) 0.016(3) -0.023(3) N1 0.057(4) 0.138(6) 0.069(4) 0.011(4) 0.009(3) -0.024(3) N2 0.071(4) 0.120(6) 0.062(4) 0.008(4) 0.028(3) 0.017(3) C5 0.060(5) 0.133(8) 0.059(4) 0.010(4) 0.004(3) -0.024(4) C4 0.050(4) 0.113(7) 0.059(5) 0.009(4) 0.012(3) -0.019(4) C3 0.049(4) 0.076(5) 0.064(5) 0.002(4) 0.013(3) -0.015(3) C2 0.051(4) 0.097(6) 0.064(4) 0.011(4) 0.007(3) -0.008(4) C1 0.049(4) 0.099(7) 0.082(6) 0.006(4) 0.012(4) -0.009(4) C6 0.048(4) 0.114(7) 0.065(4) 0.003(4) 0.009(3) -0.021(4) C7 0.039(3) 0.088(6) 0.057(4) 0.001(4) 0.010(3) -0.004(4) C8 0.052(4) 0.097(6) 0.073(5) -0.010(5) 0.002(4) 0.007(4) C9 0.044(4) 0.118(8) 0.053(4) -0.013(5) 0.005(3) 0.012(4) C10 0.056(5) 0.172(10) 0.081(6) -0.039(6) -0.009(4) 0.025(5) C11 0.042(5) 0.269(17) 0.077(7) -0.045(9) 0.009(4) 0.016(7) C12 0.049(5) 0.306(19) 0.057(5) -0.013(9) 0.017(4) -0.026(8) C13 0.057(4) 0.184(10) 0.064(5) 0.004(6) 0.023(4) -0.011(5) C14 0.039(4) 0.140(9) 0.048(4) 0.004(5) 0.011(3) 0.000(4) C15 0.053(4) 0.099(6) 0.060(4) 0.015(4) 0.013(3) -0.002(4) C16 0.032(3) 0.111(7) 0.054(4) 0.002(4) 0.006(3) 0.010(4) C17 0.048(4) 0.115(7) 0.081(5) -0.002(5) 0.018(3) 0.004(4) C18 0.059(4) 0.076(5) 0.066(5) 0.011(4) 0.014(3) 0.008(4) C22 0.050(4) 0.096(6) 0.069(4) 0.005(4) 0.013(3) 0.007(4) C21 0.057(4) 0.088(6) 0.078(5) 0.007(4) 0.024(4) 0.006(4) C20 0.062(5) 0.151(8) 0.068(5) -0.002(5) 0.025(4) 0.026(5) C19 0.051(4) 0.130(7) 0.065(5) -0.009(5) 0.012(4) 0.015(4) C23 0.076(5) 0.097(7) 0.065(5) -0.004(5) 0.022(4) -0.012(4) O3A 0.055(6) 0.135(10) 0.060(5) -0.013(6) 0.028(4) -0.029(5) O4A 0.044(6) 0.188(11) 0.052(6) 0.004(6) 0.017(5) -0.027(7) C24A 0.033(7) 0.113(12) 0.039(6) -0.020(7) -0.004(4) 0.007(7) C25A 0.050(7) 0.101(11) 0.044(7) 0.001(7) 0.022(5) 0.007(7) C26A 0.045(8) 0.094(13) 0.049(8) 0.006(7) 0.019(6) 0.008(8) O3B 0.061(12) 0.19(2) 0.073(11) 0.016(15) 0.013(8) -0.026(13) O4B 0.046(12) 0.23(3) 0.113(18) 0.067(17) 0.041(12) 0.007(15) C24B 0.12(3) 0.10(3) 0.12(2) -0.05(2) -0.004(18) 0.00(2) C25B 0.073(18) 0.24(5) 0.074(17) 0.05(3) 0.037(13) 0.03(2) C26B 0.063(19) 0.09(3) 0.17(4) 0.03(2) -0.01(2) -0.002(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 C3 1.730(6) . ? S1 C6 1.821(6) . ? S2 C18 1.746(6) . ? S2 C17 1.826(6) . ? O1 C23 1.292(4) . ? O2 C23 1.204(4) . ? N1 C1 1.322(8) . ? N1 C5 1.329(8) . ? N2 C21 1.327(8) . ? N2 C20 1.333(8) . ? C5 C4 1.378(9) . ? C4 C3 1.382(8) . ? C3 C2 1.391(8) . ? C2 C1 1.363(9) . ? C6 C7 1.501(8) . ? C7 C8 1.356(9) . ? C7 C16 1.413(10) . ? C8 C9 1.405(10) . ? C9 C14 1.402(10) . ? C9 C10 1.417(10) . ? C10 C11 1.373(13) . ? C11 C12 1.372(16) . ? C12 C13 1.386(14) . ? C13 C14 1.410(9) . ? C14 C15 1.409(10) . ? C15 C16 1.386(8) . ? C16 C17 1.505(9) . ? C18 C19 1.361(9) . ? C18 C22 1.415(8) . ? C22 C21 1.355(8) . ? C20 C19 1.346(9) . ? C23 C24B 1.48(3) . ? C23 C24A 1.522(8) . ? O3A C26A 1.311(5) . ? O4A C26A 1.209(5) . ? C24A C25A 1.308(15) . ? C25A C26A 1.501(9) . ? O3B C26B 1.310(5) . ? O4B C26B 1.209(5) . ? C24B C25B 1.535(10) . ? C24B C25B 1.582(14) 3_866 ? C25B C26B 1.501(10) . ? C25B C24B 1.582(14) 3_866 ? 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 C3 S1 C6 104.2(3) . . ? C18 S2 C17 105.3(3) . . ? C1 N1 C5 116.7(6) . . ? C21 N2 C20 116.9(6) . . ? N1 C5 C4 123.8(7) . . ? C5 C4 C3 119.2(6) . . ? C4 C3 C2 116.6(6) . . ? C4 C3 S1 125.0(5) . . ? C2 C3 S1 118.4(5) . . ? C1 C2 C3 120.0(6) . . ? N1 C1 C2 123.7(6) . . ? C7 C6 S1 109.7(4) . . ? C8 C7 C16 118.9(6) . . ? C8 C7 C6 120.2(8) . . ? C16 C7 C6 120.9(7) . . ? C7 C8 C9 123.5(8) . . ? C14 C9 C8 118.3(7) . . ? C14 C9 C10 119.8(8) . . ? C8 C9 C10 121.9(10) . . ? C11 C10 C9 119.1(10) . . ? C12 C11 C10 121.5(11) . . ? C11 C12 C13 120.6(10) . . ? C12 C13 C14 119.6(10) . . ? C9 C14 C15 118.3(6) . . ? C9 C14 C13 119.3(8) . . ? C15 C14 C13 122.4(10) . . ? C16 C15 C14 122.3(8) . . ? C15 C16 C7 118.7(7) . . ? C15 C16 C17 117.9(8) . . ? C7 C16 C17 123.3(6) . . ? C16 C17 S2 111.1(5) . . ? C19 C18 C22 116.0(6) . . ? C19 C18 S2 127.6(5) . . ? C22 C18 S2 116.4(5) . . ? C21 C22 C18 118.8(6) . . ? N2 C21 C22 123.9(6) . . ? N2 C20 C19 122.9(7) . . ? C20 C19 C18 121.4(6) . . ? O2 C23 O1 124.4(6) . . ? O2 C23 C24B 133.7(8) . . ? O1 C23 C24B 91.0(9) . . ? O2 C23 C24A 121.7(6) . . ? O1 C23 C24A 113.9(6) . . ? C24B C23 C24A 38.9(11) . . ? C25A C24A C23 123.9(9) . . ? C24A C25A C26A 121.1(9) . . ? O4A C26A O3A 121.9(9) . . ? O4A C26A C25A 127.1(9) . . ? O3A C26A C25A 111.0(8) . . ? C23 C24B C25B 98.4(18) . . ? C23 C24B C25B 113(2) . 3_866 ? C25B C24B C25B 90.2(4) . 3_866 ? C26B C25B C24B 113(2) . . ? C26B C25B C24B 121(3) . 3_866 ? C24B C25B C24B 89.8(4) . 3_866 ? O4B C26B O3B 116.9(18) . . ? O4B C26B C25B 129.0(19) . . ? O3B C26B C25B 113.8(17) . . ? _chemical_name_common ;2,3-bis(4-methylenethiopyridyl)naphthalene-fumaric acid 2/2 36% SCSC ; data_2,3-4-pyr-nap _database_code_depnum_ccdc_archive 'CCDC 277442' _audit_creation_date 2005-05-21T13:39:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,3-bis(4-methylenethiopyridyl)naphthalene ; _chemical_formula_sum 'C22 H18 N2 S2' _chemical_formula_weight 374.5 _chemical_formula_moiety 'C22 H18 N2 S2' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4183(9) _cell_length_b 10.0041(10) _cell_length_c 11.1304(11) _cell_angle_alpha 98.066(5) _cell_angle_beta 100.857(5) _cell_angle_gamma 112.583(5) _cell_volume 924.46(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_special_details ; ? ; _exptl_crystal_colour colourless _exptl_crystal_description prism #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_number 7701 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.97 _diffrn_measured_fraction_theta_max 0.97 _reflns_number_total 4118 _reflns_number_gt 2894 _reflns_threshold_expression >2sigma(I) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _space_group_name_H-M_alt P-1 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. All non-hydrogen atoms were refined according to the anisotropic model. Positions of hydrogen atoms bonded to carbon atoms were calculated on the basis of the hybridization of the belonging carbon atom. ; _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^)+(0.0591P)^2^+0.1927P] 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 none _refine_ls_number_reflns 4118 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.122 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.867 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.28792(7) 0.15642(6) 0.35090(5) 0.03649(17) Uani 1 1 d . . . S2 S 0.81324(7) 0.51122(7) 0.71429(5) 0.04013(18) Uani 1 1 d . . . C14 C 0.3467(2) 0.4089(2) 0.80141(18) 0.0304(4) Uani 1 1 d . . . C6 C 0.3899(2) 0.1236(2) 0.49286(17) 0.0292(4) Uani 1 1 d . . . H6A H 0.3376 0.0203 0.4964 0.035 Uiso 1 1 calc R . . H6B H 0.5 0.1466 0.4936 0.035 Uiso 1 1 calc R . . C18 C 0.9606(2) 0.6153(2) 0.64654(17) 0.0272(4) Uani 1 1 d . . . C16 C 0.4917(2) 0.3777(2) 0.64745(17) 0.0277(4) Uani 1 1 d . . . C8 C 0.2623(2) 0.1676(2) 0.66043(18) 0.0310(5) Uani 1 1 d . . . H8 H 0.1928 0.0672 0.6325 0.037 Uiso 1 1 calc R . . C17 C 0.6302(2) 0.4489(2) 0.59224(18) 0.0302(4) Uani 1 1 d . . . H17A H 0.6231 0.5326 0.5613 0.036 Uiso 1 1 calc R . . H17B H 0.6276 0.3772 0.5225 0.036 Uiso 1 1 calc R . . N2 N 1.2165(2) 0.7815(2) 0.55684(19) 0.0416(5) Uani 1 1 d . . . C9 C 0.2400(2) 0.2560(2) 0.76067(18) 0.0306(4) Uani 1 1 d . . . N1 N 0.3309(3) -0.1373(2) 0.01932(18) 0.0464(5) Uani 1 1 d . . . C22 C 0.9350(3) 0.6369(2) 0.52548(19) 0.0315(5) Uani 1 1 d . . . H22 H 0.8326 0.5969 0.4721 0.038 Uiso 1 1 calc R . . C21 C 1.0657(3) 0.7195(2) 0.4860(2) 0.0368(5) Uani 1 1 d . . . H21 H 1.0473 0.7328 0.4044 0.044 Uiso 1 1 calc R . . C7 C 0.3822(2) 0.2247(2) 0.60333(18) 0.0285(4) Uani 1 1 d . . . C15 C 0.4713(2) 0.4656(2) 0.74378(18) 0.0309(4) Uani 1 1 d . . . H15 H 0.5422 0.5656 0.7716 0.037 Uiso 1 1 calc R . . C12 C 0.1996(3) 0.4421(3) 0.9499(2) 0.0434(6) Uani 1 1 d . . . H12 H 0.1839 0.5029 1.0124 0.052 Uiso 1 1 calc R . . C19 C 1.1165(3) 0.6804(2) 0.7223(2) 0.0369(5) Uani 1 1 d . . . H19 H 1.1381 0.6694 0.8045 0.044 Uiso 1 1 calc R . . C3 C 0.3096(2) 0.0421(2) 0.22766(18) 0.0281(4) Uani 1 1 d . . . C4 C 0.3594(3) -0.0697(2) 0.24121(19) 0.0361(5) Uani 1 1 d . . . H4 H 0.3869 -0.0876 0.3201 0.043 Uiso 1 1 calc R . . C10 C 0.1158(3) 0.1986(3) 0.8190(2) 0.0387(5) Uani 1 1 d . . . H10 H 0.0473 0.0978 0.7944 0.046 Uiso 1 1 calc R . . C13 C 0.3224(3) 0.5014(3) 0.89800(19) 0.0382(5) Uani 1 1 d . . . H13 H 0.3907 0.6022 0.9253 0.046 Uiso 1 1 calc R . . C2 C 0.2707(3) 0.0630(2) 0.10662(19) 0.0389(5) Uani 1 1 d . . . H2 H 0.2361 0.1363 0.0926 0.047 Uiso 1 1 calc R . . C20 C 1.2381(3) 0.7609(3) 0.6744(2) 0.0425(5) Uani 1 1 d . . . H20 H 1.3415 0.8036 0.7265 0.051 Uiso 1 1 calc R . . C5 C 0.3675(3) -0.1543(3) 0.1352(2) 0.0432(6) Uani 1 1 d . . . H5 H 0.4011 -0.2289 0.1464 0.052 Uiso 1 1 calc R . . C11 C 0.0953(3) 0.2885(3) 0.9099(2) 0.0444(6) Uani 1 1 d . . . H11 H 0.012 0.2493 0.9466 0.053 Uiso 1 1 calc R . . C1 C 0.2845(3) -0.0273(3) 0.0080(2) 0.0485(6) Uani 1 1 d . . . H1 H 0.2599 -0.0109 -0.0719 0.058 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 S1 0.0461(4) 0.0395(3) 0.0280(3) 0.0022(2) 0.0035(2) 0.0272(3) S2 0.0287(3) 0.0595(4) 0.0295(3) 0.0181(2) 0.0082(2) 0.0131(3) C14 0.0301(11) 0.0353(11) 0.0263(10) 0.0090(8) 0.0056(8) 0.0146(9) C6 0.0325(11) 0.0313(11) 0.0268(10) 0.0069(8) 0.0080(8) 0.0164(9) C18 0.0269(11) 0.0299(10) 0.0263(9) 0.0049(8) 0.0073(8) 0.0141(9) C16 0.0286(11) 0.0309(11) 0.0244(9) 0.0079(8) 0.0069(8) 0.0129(9) C8 0.0310(11) 0.0271(10) 0.0327(11) 0.0085(8) 0.0061(9) 0.0105(9) C17 0.0275(11) 0.0346(11) 0.0243(9) 0.0040(8) 0.0058(8) 0.0102(9) N2 0.0371(11) 0.0348(10) 0.0561(12) 0.0137(9) 0.0202(10) 0.0138(9) C9 0.0297(11) 0.0343(11) 0.0288(10) 0.0125(8) 0.0068(8) 0.0134(9) N1 0.0542(13) 0.0506(12) 0.0331(10) -0.0011(8) 0.0071(9) 0.0266(11) C22 0.0312(11) 0.0369(12) 0.0300(10) 0.0081(8) 0.0096(9) 0.0173(10) C21 0.0407(13) 0.0403(12) 0.0388(12) 0.0159(9) 0.0163(10) 0.0220(11) C7 0.0303(11) 0.0318(11) 0.0268(9) 0.0091(8) 0.0062(8) 0.0165(9) C15 0.0295(11) 0.0280(10) 0.0299(10) 0.0040(8) 0.0066(8) 0.0081(9) C12 0.0498(15) 0.0570(15) 0.0318(11) 0.0082(10) 0.0173(11) 0.0289(13) C19 0.0327(12) 0.0415(13) 0.0316(11) 0.0053(9) 0.0049(9) 0.0133(10) C3 0.0242(10) 0.0270(10) 0.0267(9) 0.0018(8) 0.0041(8) 0.0069(8) C4 0.0429(13) 0.0375(12) 0.0266(10) 0.0023(8) 0.0009(9) 0.0212(11) C10 0.0350(13) 0.0407(13) 0.0397(12) 0.0140(10) 0.0141(10) 0.0119(10) C13 0.0439(14) 0.0408(13) 0.0299(11) 0.0045(9) 0.0109(10) 0.0187(11) C2 0.0476(14) 0.0366(12) 0.0327(11) 0.0104(9) 0.0063(10) 0.0194(11) C20 0.0267(12) 0.0445(13) 0.0497(14) 0.0072(11) 0.0072(10) 0.0107(10) C5 0.0496(15) 0.0441(13) 0.0359(12) -0.0016(10) 0.0025(11) 0.0277(12) C11 0.0430(14) 0.0565(15) 0.0394(12) 0.0164(11) 0.0212(11) 0.0206(12) C1 0.0633(17) 0.0530(15) 0.0283(11) 0.0106(10) 0.0098(11) 0.0244(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 C3 1.7538(19) . ? S1 C6 1.829(2) . ? S2 C18 1.756(2) . ? S2 C17 1.806(2) . ? C14 C15 1.409(3) . ? C14 C9 1.417(3) . ? C14 C13 1.428(3) . ? C6 C7 1.510(3) . ? C18 C22 1.386(3) . ? C18 C19 1.392(3) . ? C16 C15 1.379(3) . ? C16 C7 1.426(3) . ? C16 C17 1.516(3) . ? C8 C7 1.372(3) . ? C8 C9 1.423(3) . ? N2 C21 1.337(3) . ? N2 C20 1.343(3) . ? C9 C10 1.412(3) . ? N1 C5 1.324(3) . ? N1 C1 1.344(3) . ? C22 C21 1.384(3) . ? C12 C13 1.358(3) . ? C12 C11 1.417(4) . ? C19 C20 1.374(3) . ? C3 C4 1.384(3) . ? C3 C2 1.394(3) . ? C4 C5 1.385(3) . ? C10 C11 1.350(3) . ? C2 C1 1.379(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 C3 S1 C6 103.90(9) . . ? C18 S2 C17 103.73(9) . . ? C15 C14 C9 119.07(18) . . ? C15 C14 C13 122.04(19) . . ? C9 C14 C13 118.87(19) . . ? C7 C6 S1 106.62(13) . . ? C22 C18 C19 117.93(19) . . ? C22 C18 S2 125.89(16) . . ? C19 C18 S2 116.18(15) . . ? C15 C16 C7 119.13(18) . . ? C15 C16 C17 118.19(17) . . ? C7 C16 C17 122.68(17) . . ? C7 C8 C9 122.60(18) . . ? C16 C17 S2 108.27(13) . . ? C21 N2 C20 115.91(19) . . ? C10 C9 C14 119.19(19) . . ? C10 C9 C8 122.99(19) . . ? C14 C9 C8 117.81(18) . . ? C5 N1 C1 115.37(19) . . ? C21 C22 C18 118.3(2) . . ? N2 C21 C22 124.7(2) . . ? C8 C7 C16 119.15(18) . . ? C8 C7 C6 118.48(18) . . ? C16 C7 C6 122.34(17) . . ? C16 C15 C14 122.19(19) . . ? C13 C12 C11 120.7(2) . . ? C20 C19 C18 119.3(2) . . ? C4 C3 C2 117.44(18) . . ? C4 C3 S1 124.79(15) . . ? C2 C3 S1 117.75(16) . . ? C3 C4 C5 118.9(2) . . ? C11 C10 C9 120.8(2) . . ? C12 C13 C14 120.0(2) . . ? C1 C2 C3 118.7(2) . . ? N2 C20 C19 123.9(2) . . ? N1 C5 C4 125.0(2) . . ? C10 C11 C12 120.5(2) . . ? N1 C1 C2 124.6(2) . . ? _chemical_name_common 2,3-bis(4-methylenethiopyridyl)naphthalene