# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Narcis Avarvari' _publ_contact_author_address ; Department of Chemistry CNRS-Université d'Angers 2 Bd. Lavoisier, UFR Sciences, Bât. ANGERS 49045 FRANCE ; _publ_contact_author_email NARCIS.AVARVARI@UNIV-ANGERS.FR _publ_section_title ; [2+2]photocyclization in a single-crystal-to-single-crystal transformation of a TTF-amido-pyridine ; loop_ _publ_author_name 'Narcis Avarvari' 'Patrick Batail' 'Thomas Devic' data_1 _database_code_depnum_ccdc_archive 'CCDC 235419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; -3,4-ethylenedithio-4'-(-3-pyridincarmaboyl)tetrathiafulvalene, tetrahydrofurane solvate. ; _chemical_name_common ; -3,4-ethylenedithio-4'-(-3- pyridincarmaboyl)tetrathiafulvalene, tetrahydrofurane solvate. ; _chemical_melting_point ? _chemical_formula_moiety '2(C14H10S6N2O), C4H8O' _chemical_formula_sum 'C16 H14 N2 O1.50 S6' _chemical_formula_weight 450.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.3412(15) _cell_length_b 11.6686(15) _cell_length_c 24.183(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3764.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 87 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.738 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7506 _exptl_absorpt_correction_T_max 0.9254 _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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42389 _diffrn_reflns_av_R_equivalents 0.1198 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 24.50 _reflns_number_total 3110 _reflns_number_gt 2141 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0510P)^2^+9.8494P] 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 3110 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S1 S 0.91604(10) -0.00358(12) 0.39763(5) 0.0463(4) Uani 1 1 d . . . S2 S 0.95595(11) 0.23557(12) 0.43227(6) 0.0512(4) Uani 1 1 d . . . S3 S 1.02344(10) 0.05434(12) 0.27778(5) 0.0478(4) Uani 1 1 d . . . S4 S 1.05052(11) 0.29362(12) 0.31463(6) 0.0526(4) Uani 1 1 d . . . S5 S 1.15393(14) 0.07766(13) 0.17975(6) 0.0680(5) Uani 1 1 d . . . S6 S 1.19123(11) 0.35961(12) 0.22717(6) 0.0526(4) Uani 1 1 d . . . C1 C 0.8929(3) 0.0338(4) 0.46690(19) 0.0398(12) Uani 1 1 d . . . C2 C 0.9119(4) 0.1419(4) 0.4814(2) 0.0438(13) Uani 1 1 d . . . H2 H 0.904(4) 0.172(4) 0.519(2) 0.049(14) Uiso 1 1 d . . . C3 C 0.9671(3) 0.1306(4) 0.38047(19) 0.0393(12) Uani 1 1 d . . . C4 C 1.0090(3) 0.1545(4) 0.33151(19) 0.0401(12) Uani 1 1 d . . . C5 C 1.1048(4) 0.1429(5) 0.23919(19) 0.0431(12) Uani 1 1 d . . . C6 C 1.1182(4) 0.2502(4) 0.2556(2) 0.0405(12) Uani 1 1 d . . . C7 C 1.1831(5) 0.2039(5) 0.1402(2) 0.0565(16) Uani 1 1 d . . . H7A H 1.214(4) 0.177(5) 0.107(2) 0.068(18) Uiso 1 1 d . . . H7B H 1.120(4) 0.246(5) 0.128(2) 0.061(16) Uiso 1 1 d . . . C8 C 1.2494(6) 0.2855(7) 0.1699(3) 0.0668(19) Uani 1 1 d . . . H8A H 1.304(5) 0.258(5) 0.182(2) 0.07(2) Uiso 1 1 d . . . H8B H 1.269(5) 0.343(5) 0.149(2) 0.07(2) Uiso 1 1 d . . . C9 C 0.8483(3) -0.0627(5) 0.49868(19) 0.0396(12) Uani 1 1 d . . . O1 O 0.8347(3) -0.1542(3) 0.47514(14) 0.0588(10) Uani 1 1 d . . . N1 N 0.8230(3) -0.0437(4) 0.55206(16) 0.0376(10) Uani 1 1 d . . . H1 H 0.829(3) 0.019(4) 0.5634(15) 0.009(11) Uiso 1 1 d . . . C10 C 0.7686(3) -0.1187(4) 0.58729(18) 0.0351(11) Uani 1 1 d . . . C11 C 0.7327(4) -0.0773(5) 0.6368(2) 0.0451(13) Uani 1 1 d . . . H11 H 0.748(4) 0.001(5) 0.647(2) 0.053(15) Uiso 1 1 d . . . C12 C 0.6755(4) -0.1475(5) 0.6700(2) 0.0534(15) Uani 1 1 d . . . H12 H 0.656(4) -0.124(5) 0.707(2) 0.077(19) Uiso 1 1 d . . . C13 C 0.6555(4) -0.2575(5) 0.6522(2) 0.0500(15) Uani 1 1 d . . . H13 H 0.625(4) -0.299(5) 0.673(2) 0.064(19) Uiso 1 1 d . . . C14 C 0.7485(4) -0.2316(4) 0.5742(2) 0.0437(13) Uani 1 1 d . . . H14 H 0.769(4) -0.256(4) 0.540(2) 0.047(14) Uiso 1 1 d . . . N2 N 0.6908(3) -0.2996(4) 0.60541(17) 0.0466(11) Uani 1 1 d . . . C15 C 0.5848(6) 0.0183(8) 0.4839(5) 0.115(3) Uani 1 1 d . . . C16 C 0.4936(7) 0.0525(8) 0.4568(3) 0.111(3) Uani 1 1 d . . . O17 O 0.5849(7) -0.0756(10) 0.5133(4) 0.086(3) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0538(8) 0.0462(8) 0.0390(7) -0.0025(6) 0.0037(6) -0.0089(7) S2 0.0562(9) 0.0427(8) 0.0547(8) -0.0041(6) 0.0116(7) -0.0050(7) S3 0.0538(8) 0.0436(8) 0.0459(7) 0.0016(6) 0.0030(6) -0.0075(7) S4 0.0589(9) 0.0414(8) 0.0575(8) -0.0012(7) 0.0190(7) -0.0024(7) S5 0.1069(13) 0.0437(9) 0.0534(9) 0.0029(7) 0.0258(9) 0.0099(9) S6 0.0546(9) 0.0455(9) 0.0578(8) 0.0045(7) 0.0152(7) -0.0043(7) C1 0.029(3) 0.048(3) 0.042(3) 0.003(2) 0.000(2) -0.003(2) C2 0.045(3) 0.042(3) 0.045(3) -0.008(3) 0.005(2) 0.002(3) C3 0.034(3) 0.041(3) 0.043(3) 0.000(2) 0.000(2) 0.004(2) C4 0.032(3) 0.045(3) 0.043(3) 0.002(2) -0.001(2) 0.000(2) C5 0.042(3) 0.044(3) 0.043(3) 0.008(2) 0.000(2) -0.004(3) C6 0.038(3) 0.040(3) 0.043(3) 0.003(2) 0.001(2) 0.000(2) C7 0.068(4) 0.054(4) 0.047(3) 0.007(3) 0.013(3) 0.008(3) C8 0.050(4) 0.070(5) 0.080(5) -0.005(4) 0.019(4) -0.002(4) C9 0.033(3) 0.046(3) 0.040(3) -0.003(2) 0.002(2) -0.001(2) O1 0.080(3) 0.045(2) 0.052(2) -0.0110(19) 0.0126(19) -0.016(2) N1 0.043(3) 0.029(3) 0.041(2) -0.004(2) -0.0001(19) -0.004(2) C10 0.032(3) 0.038(3) 0.035(2) 0.003(2) -0.002(2) 0.000(2) C11 0.054(3) 0.040(3) 0.042(3) -0.002(2) 0.004(3) -0.003(3) C12 0.064(4) 0.049(4) 0.048(3) 0.001(3) 0.011(3) 0.002(3) C13 0.053(3) 0.049(4) 0.049(3) 0.012(3) 0.006(3) -0.009(3) C14 0.050(3) 0.042(3) 0.040(3) -0.001(3) 0.003(3) -0.003(3) N2 0.053(3) 0.038(3) 0.049(3) 0.001(2) 0.002(2) -0.007(2) C15 0.081(6) 0.077(6) 0.185(10) 0.015(6) -0.027(6) 0.000(5) C16 0.109(6) 0.123(7) 0.100(6) -0.012(5) 0.000(6) 0.058(6) O17 0.061(6) 0.125(9) 0.072(6) 0.003(6) -0.018(5) 0.013(6) _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 1.757(5) . ? S1 C1 1.758(5) . ? S2 C2 1.718(5) . ? S2 C3 1.758(5) . ? S3 C4 1.758(5) . ? S3 C5 1.766(5) . ? S4 C4 1.763(5) . ? S4 C6 1.764(5) . ? S5 C5 1.754(5) . ? S5 C7 1.799(6) . ? S6 C6 1.747(5) . ? S6 C8 1.808(7) . ? C1 C2 1.334(7) . ? C1 C9 1.487(7) . ? C1 C2 3.543(7) 5_756 ? C3 C4 1.338(6) . ? C5 C6 1.325(7) . ? C7 C8 1.484(9) . ? C9 O1 1.224(6) . ? C9 N1 1.353(6) . ? N1 C10 1.420(6) . ? C10 C11 1.377(7) . ? C10 C14 1.381(7) . ? C11 C12 1.378(8) . ? C12 C13 1.380(8) . ? C13 N2 1.320(7) . ? C14 N2 1.339(6) . ? C15 O17 1.305(12) . ? C15 C16 1.439(11) . ? C15 C16 1.957(14) 5_656 ? C16 O17 1.302(12) 5_656 ? C16 C15 1.957(14) 5_656 ? O17 C16 1.302(12) 5_656 ? 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 C1 94.1(2) . . ? C2 S2 C3 94.5(2) . . ? C4 S3 C5 93.9(2) . . ? C4 S4 C6 94.8(2) . . ? C5 S5 C7 99.3(3) . . ? C6 S6 C8 101.0(3) . . ? C2 C1 C9 131.0(5) . . ? C2 C1 S1 116.9(4) . . ? C9 C1 S1 112.0(4) . . ? C2 C1 C2 108.3(3) . 5_756 ? C9 C1 C2 70.9(3) . 5_756 ? S1 C1 C2 93.6(2) . 5_756 ? C1 C2 S2 119.0(4) . . ? C4 C3 S1 123.8(4) . . ? C4 C3 S2 121.4(4) . . ? S1 C3 S2 114.8(3) . . ? C3 C4 S3 124.1(4) . . ? C3 C4 S4 121.8(4) . . ? S3 C4 S4 114.0(3) . . ? C6 C5 S5 127.2(4) . . ? C6 C5 S3 118.5(4) . . ? S5 C5 S3 114.1(3) . . ? C5 C6 S6 130.4(4) . . ? C5 C6 S4 116.4(4) . . ? S6 C6 S4 113.2(3) . . ? C8 C7 S5 113.3(5) . . ? C7 C8 S6 114.9(5) . . ? O1 C9 N1 123.3(5) . . ? O1 C9 C1 118.7(4) . . ? N1 C9 C1 118.0(5) . . ? C9 N1 C10 126.8(5) . . ? C11 C10 C14 117.8(5) . . ? C11 C10 N1 118.9(5) . . ? C14 C10 N1 123.3(4) . . ? C10 C11 C12 119.4(5) . . ? C11 C12 C13 118.6(5) . . ? N2 C13 C12 123.0(5) . . ? N2 C14 C10 123.2(5) . . ? C13 N2 C14 117.9(5) . . ? O17 C15 C16 118.8(9) . . ? O17 C15 C16 41.3(6) . 5_656 ? C16 C15 C16 90.0(7) . 5_656 ? O17 C16 C15 118.9(9) 5_656 . ? O17 C16 C15 41.4(6) 5_656 5_656 ? C15 C16 C15 90.0(7) . 5_656 ? C16 O17 C15 97.3(9) 5_656 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.476 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.080 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 235420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(-3,4-ethylenedithio-4'-(-3-pyridincarmaboyl)tetrathiafulvalene), tetrahydrofurane solvate. ; _chemical_name_common ; bis(-3,4-ethylenedithio-4'-(-3- pyridincarmaboyl)tetrathiafulvalene), tetrahydrofurane solvate. ; _chemical_melting_point ? _chemical_formula_moiety '2(C14H10S6N2O), C4H8O' _chemical_formula_sum 'C32 H28 N4 O3 S12' _chemical_formula_weight 901.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3756(13) _cell_length_b 11.1605(7) _cell_length_c 22.9236(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3677.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6400 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.8 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.755 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'rotation, phi incr. 1' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23684 _diffrn_reflns_av_R_equivalents 0.1450 _diffrn_reflns_av_sigmaI/netI 0.3544 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.86 _reflns_number_total 3536 _reflns_number_gt 1083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE, Stoe-IPDS' _computing_cell_refinement 'CELL, Stoe-IPDS' _computing_data_reduction 'INTEGRATE, Stoe-IPDS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _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^)+(0.0201P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3536 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1690 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 0.595 _refine_ls_restrained_S_all 0.595 _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 S1 S 1.08749(13) -0.03585(17) 0.59739(6) 0.0377(5) Uani 1 1 d . . . S2 S 1.04465(13) 0.20235(15) 0.55225(7) 0.0404(5) Uani 1 1 d . . . S3 S 0.98121(12) 0.02619(16) 0.71862(7) 0.0373(5) Uani 1 1 d . . . S4 S 0.94863(13) 0.27140(16) 0.67765(7) 0.0418(5) Uani 1 1 d . . . S5 S 0.85253(15) 0.04051(17) 0.81764(7) 0.0507(6) Uani 1 1 d . . . S6 S 0.80985(13) 0.33343(16) 0.76722(7) 0.0428(5) Uani 1 1 d . . . C1 C 1.0653(4) -0.0369(6) 0.5197(2) 0.0274(16) Uani 1 1 d . . . C2 C 1.0345(4) 0.0875(6) 0.4973(3) 0.0334(18) Uani 1 1 d . . . H2 H 1.0695 0.1096 0.4622 0.040 Uiso 1 1 calc R . . C3 C 1.0326(5) 0.1018(6) 0.6098(3) 0.0350(18) Uani 1 1 d . . . C4 C 0.9919(5) 0.1281(6) 0.6613(3) 0.0332(18) Uani 1 1 d . . . C5 C 0.8998(5) 0.1116(6) 0.7573(3) 0.0330(17) Uani 1 1 d . . . C6 C 0.8845(4) 0.2241(5) 0.7388(3) 0.0320(17) Uani 1 1 d . . . C7 C 0.8174(6) 0.1685(7) 0.8594(3) 0.055(2) Uani 1 1 d . . . H7A H 0.7853 0.1418 0.8943 0.065 Uiso 1 1 calc R . . H7B H 0.8722 0.2127 0.8715 0.065 Uiso 1 1 calc R . . C8 C 0.7537(6) 0.2513(7) 0.8249(3) 0.063(2) Uani 1 1 d . . . H8A H 0.7257 0.3081 0.8517 0.075 Uiso 1 1 calc R . . H8B H 0.7039 0.2039 0.8081 0.075 Uiso 1 1 calc R . . O1 O 1.1733(4) -0.1931(5) 0.51878(18) 0.0563(15) Uani 1 1 d . . . C9 C 1.1439(5) -0.1061(6) 0.4933(3) 0.0350(18) Uani 1 1 d . . . N1 N 1.1770(3) -0.0716(4) 0.4406(2) 0.0312(14) Uani 1 1 d . . . H1 H 1.1554 -0.0056 0.4267 0.037 Uiso 1 1 calc R . . C10 C 1.2438(5) -0.1328(6) 0.4060(2) 0.0278(17) Uani 1 1 d . . . C11 C 1.2786(5) -0.0775(6) 0.3574(3) 0.0371(19) Uani 1 1 d . . . H11 H 1.2585 -0.0010 0.3474 0.045 Uiso 1 1 calc R . . C12 C 1.3432(5) -0.1353(6) 0.3236(3) 0.046(2) Uani 1 1 d . . . H12 H 1.3658 -0.0998 0.2897 0.055 Uiso 1 1 calc R . . C13 C 1.3737(4) -0.2452(7) 0.3403(3) 0.0402(19) Uani 1 1 d . . . H13 H 1.4206 -0.2816 0.3187 0.048 Uiso 1 1 calc R . . N2 N 1.3397(4) -0.3031(5) 0.3863(2) 0.0372(15) Uani 1 1 d . . . C14 C 1.2735(3) -0.2464(4) 0.42027(18) 0.0339(18) Uani 1 1 d . . . H14 H 1.2490 -0.2850 0.4528 0.041 Uiso 1 1 calc R . . C15 C 0.5045(3) 0.0390(4) 0.54829(18) 0.088(3) Uiso 1 1 d R . . C16 C 0.4199(3) 0.0085(4) 0.50439(18) 0.115(4) Uiso 1 1 d R . . O2 O 0.5783(3) 0.0845(4) 0.52447(18) 0.251(11) Uiso 0.50 1 d PR . . 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 0.0458(12) 0.0414(11) 0.0258(9) 0.0032(9) 0.0014(9) 0.0076(11) S2 0.0536(13) 0.0313(10) 0.0362(10) 0.0026(9) 0.0051(10) -0.0029(10) S3 0.0462(12) 0.0354(11) 0.0303(9) -0.0008(9) -0.0030(9) 0.0026(10) S4 0.0539(12) 0.0342(11) 0.0372(10) 0.0000(10) 0.0099(10) -0.0015(11) S5 0.0867(16) 0.0338(11) 0.0315(9) -0.0014(10) 0.0120(11) -0.0062(12) S6 0.0507(12) 0.0389(11) 0.0388(11) -0.0011(9) 0.0094(10) 0.0043(11) C1 0.016(4) 0.033(4) 0.033(3) 0.006(3) 0.008(3) 0.009(4) C2 0.029(5) 0.038(4) 0.033(4) 0.007(3) 0.015(4) 0.003(4) C3 0.033(5) 0.042(4) 0.030(4) -0.002(3) -0.005(3) 0.004(4) C4 0.033(4) 0.036(4) 0.030(4) -0.005(3) -0.008(3) -0.004(4) C5 0.040(4) 0.034(4) 0.024(4) -0.006(3) -0.002(4) -0.004(4) C6 0.037(4) 0.025(4) 0.033(4) -0.004(3) -0.004(3) -0.007(3) C7 0.079(6) 0.041(5) 0.043(4) -0.001(4) 0.017(5) -0.011(5) C8 0.072(5) 0.049(6) 0.068(5) 0.009(5) 0.028(5) -0.002(5) O1 0.075(4) 0.054(3) 0.039(3) 0.017(3) 0.019(3) 0.031(3) C9 0.049(5) 0.025(4) 0.031(4) 0.005(4) 0.001(4) 0.009(4) N1 0.031(3) 0.036(3) 0.026(3) 0.003(3) 0.010(3) 0.011(3) C10 0.032(4) 0.031(4) 0.021(3) 0.006(3) -0.001(4) -0.007(4) C11 0.049(5) 0.027(4) 0.035(4) 0.007(3) 0.009(4) 0.001(4) C12 0.062(5) 0.038(5) 0.037(4) 0.003(4) 0.022(4) 0.004(4) C13 0.043(5) 0.037(5) 0.040(4) -0.005(4) 0.016(4) 0.006(4) N2 0.039(4) 0.037(4) 0.035(3) 0.007(3) -0.008(3) 0.002(3) C14 0.039(5) 0.034(4) 0.029(4) 0.002(3) 0.008(3) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.750(7) . ? S1 C1 1.809(6) . ? S2 C3 1.742(7) . ? S2 C2 1.803(6) . ? S3 C4 1.745(7) . ? S3 C5 1.750(6) . ? S4 C4 1.757(7) . ? S4 C6 1.759(6) . ? S5 C5 1.733(6) . ? S5 C7 1.792(7) . ? S6 C6 1.750(6) . ? S6 C8 1.800(7) . ? C1 C9 1.497(8) . ? C1 C2 1.545(8) . ? C1 C2 1.591(8) 5_756 ? C2 C1 1.591(8) 5_756 ? C3 C4 1.348(7) . ? C5 C6 1.344(8) . ? C7 C8 1.522(10) . ? O1 C9 1.209(7) . ? C9 N1 1.353(7) . ? N1 C10 1.422(7) . ? C10 C11 1.368(8) . ? C10 C14 1.377(7) . ? C11 C12 1.372(8) . ? C12 C13 1.358(9) . ? C13 N2 1.330(7) . ? N2 C14 1.383(6) . ? C15 O2 1.2972 . ? C15 C16 1.6148 . ? C15 C16 1.709(9) 5_656 ? C16 O2 1.231(9) 5_656 ? C16 C15 1.709(9) 5_656 ? O2 C16 1.231(9) 5_656 ? 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 C1 95.0(3) . . ? C3 S2 C2 93.6(3) . . ? C4 S3 C5 94.9(3) . . ? C4 S4 C6 94.8(3) . . ? C5 S5 C7 99.9(3) . . ? C6 S6 C8 101.1(3) . . ? C9 C1 C2 123.1(5) . . ? C9 C1 C2 113.5(5) . 5_756 ? C2 C1 C2 88.8(5) . 5_756 ? C9 C1 S1 105.6(4) . . ? C2 C1 S1 111.9(4) . . ? C2 C1 S1 113.7(4) 5_756 . ? C1 C2 C1 91.2(5) . 5_756 ? C1 C2 S2 112.5(4) . . ? C1 C2 S2 119.8(4) 5_756 . ? C4 C3 S2 124.4(5) . . ? C4 C3 S1 122.0(5) . . ? S2 C3 S1 113.4(4) . . ? C3 C4 S3 123.7(5) . . ? C3 C4 S4 122.6(5) . . ? S3 C4 S4 113.6(4) . . ? C6 C5 S5 128.0(5) . . ? C6 C5 S3 117.3(5) . . ? S5 C5 S3 114.6(4) . . ? C5 C6 S6 129.4(5) . . ? C5 C6 S4 116.5(5) . . ? S6 C6 S4 114.1(3) . . ? C8 C7 S5 112.1(5) . . ? C7 C8 S6 114.9(5) . . ? O1 C9 N1 122.5(6) . . ? O1 C9 C1 118.8(6) . . ? N1 C9 C1 118.6(6) . . ? C9 N1 C10 126.8(5) . . ? C11 C10 C14 119.8(6) . . ? C11 C10 N1 119.0(6) . . ? C14 C10 N1 121.2(5) . . ? C10 C11 C12 119.7(7) . . ? C13 C12 C11 118.9(7) . . ? N2 C13 C12 123.0(6) . . ? C13 N2 C14 118.5(5) . . ? C10 C14 N2 120.0(5) . . ? O2 C15 C16 115.9 . . ? O2 C15 C16 45.9(3) . 5_656 ? C16 C15 C16 88.5(3) . 5_656 ? O2 C16 C15 119.8(4) 5_656 . ? O2 C16 C15 49.1(3) 5_656 5_656 ? C15 C16 C15 91.5(3) . 5_656 ? C16 O2 C15 85.0(5) 5_656 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.86 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.802 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.074