Supplementary Material (ESI) for Faraday Discussions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Faraday Discuss.' _journal_coden_Cambridge 0169 #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Claude Lecomte' _publ_contact_author_address # Address of author for correspondence ;Laboratoire de Cristallographie et de Modelisation des Materiaux Mineraux et Biologiques LCM3B (UMR UHP-CNRS 7036) Faculte de Sciences et Techniques BP 239, Boulevard des Aiguillettes 54506 Vandoeuvre-les-Nancy (France) ; _publ_contact_author_email claude.lecomte@lcm3b.uhp-nancy.fr _publ_contact_author_fax '0033 (0)3 83 40 64 92' _publ_contact_author_phone '0033 (0)3 83 68 48 65' _publ_contact_letter ; ? ; # TITLE AND AUTHOR LIST _publ_section_title ; Charge density of TTF-CA: thorough investigation of intra and intermolecular interactions ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address P.Garcia ; Laboratoire de Cristallographie et de Modelisation des Materiaux Mineraux et Biologiques LCM3B (UMR UHP-CNRS 7036) Faculte de Sciences et Techniques BP 239, Boulevard des Aiguillettes 54506 Vandoeuvre-les-Nancy (France) ; S.Dahaoui ; Laboratoire de Cristallographie et de Modelisation des Materiaux Mineraux et Biologiques LCM3B (UMR UHP-CNRS 7036) Faculte de Sciences et Techniques BP 239, Boulevard des Aiguillettes 54506 Vandoeuvre-les-Nancy (France) ; C.Katan ; Synthese et ElectroSynthese Organiques, CNRS UMR 6510 Universite de Rennes I, Campus de Beaulieu, Bat 10A, Case 1003, 35402 Rennes (France) ; M.Souhassou ; Laboratoire de Cristallographie et de Modelisation des Materiaux Mineraux et Biologiques LCM3B (UMR UHP-CNRS 7036) Faculte de Sciences et Techniques BP 239, Boulevard des Aiguillettes 54506 Vandoeuvre-les-Nancy (France) ; C.Lecomte ; Laboratoire de Cristallographie et de Modelisation des Materiaux Mineraux et Biologiques LCM3B (UMR UHP-CNRS 7036) Faculte de Sciences et Techniques BP 239, Boulevard des Aiguillettes 54506 Vandoeuvre-les-Nancy (France) ; #============================================================================== # TTF-CA 105K #============================================================================== data_ttf-ca-105k-molly _database_code_depnum_ccdc_archive 'CCDC 612477' _audit_creation_method SHELXL-97 # CHEMICAL DATA _chemical_name_systematic ; Tetrathiafulvalene-p-chloranil ; _chemical_name_common Tetrathiafulvalene-p-chloranil _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 S4, C6 Cl4 O2' _chemical_formula_sum 'C12 H4 Cl4 O2 S4' _chemical_formula_weight 450.19 # CRYSTAL DATA 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.2297(5) _cell_length_b 7.5933(5) _cell_length_c 14.4980(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.15(3) _cell_angle_gamma 90.00 _cell_volume 785.78(11) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 9237 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 53.92 _exptl_crystal_description prismatic _exptl_crystal_colour black _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.284 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.877 _exptl_absorpt_process_details ; 'de Titta, 1985' ; # EXPERIMENTAL DATA _diffrn_ambient_temperature 105(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 'Enraf-Nonius difractometer' _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9237 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 53.92 _reflns_number_total 9237 _reflns_number_gt 6270 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'DENZO (Z. Otwinowski)' _computing_cell_refinement 'DENZO (Z. Otwinowski)' _computing_data_reduction 'DENZO (Z. Otwinowski)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'MOLLY (Hansen and Coppens,1978)' _computing_molecular_graphics 'ORTEP (L. Farrugia, 1997) ' _computing_publication_material 'WingX (L. Farrugia, 1999)' # REFINEMENT DATA _refine_special_details ; Reflections were merged with Sortav (Blessing, 1995). Multipolar refinement using Hansen and Coppens model (N. Hansen and P. Coppens, Acta Cryst.,2,65 (1978). ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/sig^2' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method isotropic _refine_ls_extinction_coef 0.0631(8) _refine_ls_extinction_expression 'P.J. Becker and P. Coppens, Acta Cryst. A,30,129 (1974) ' _refine_ls_number_reflns 6270 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0141 _refine_ls_wR_factor_ref 0.0257 _refine_ls_wR_factor_gt 0.0187 _refine_ls_goodness_of_fit_ref 0.87 _refine_ls_restrained_S_all 0.80 _refine_ls_shift/su_max 0.1 _refine_ls_shift/su_mean 0.01 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 S4 S 0.38492(2) 0.236541(18) 0.016058(10) 0.01238(2) Uani 1 1 d . . . S5 S 0.441757(19) 0.441863(19) -0.150103(9) 0.01182(2) Uani 1 1 d . . . C1 C 0.31047(8) 0.14212(7) -0.09341(4) 0.01357(7) Uani 1 1 d . . . H6 H 0.2538(13) 0.0241(14) -0.0946(8) 0.031(3) Uiso 1 1 d . . . C2 C 0.46242(7) 0.43279(7) -0.02837(3) 0.01151(7) Uani 1 1 d . . . C3 C 0.33570(8) 0.23636(8) -0.16838(4) 0.01356(7) Uani 1 1 d . . . H7 H 0.3006(13) 0.2016(14) -0.2326(7) 0.023(2) Uiso 1 1 d . . . C15 C 0.04414(7) 0.63945(7) -0.06243(3) 0.01109(6) Uani 1 1 d . . . C16 C -0.04362(7) 0.47124(7) -0.09896(3) 0.01082(6) Uani 1 1 d . . . C17 C -0.08015(7) 0.34066(6) -0.04081(3) 0.01063(6) Uani 1 1 d . . . O18 O 0.08922(7) 0.75295(6) -0.11435(3) 0.01539(7) Uani 1 1 d . . . Cl19 Cl -0.087197(19) 0.45033(2) -0.217658(9) 0.01472(2) Uani 1 1 d . . . Cl20 Cl -0.169303(19) 0.142674(18) -0.081909(10) 0.01363(2) 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 S4 0.01569(5) 0.00934(4) 0.01214(5) 0.00141(4) 0.00231(4) -0.00182(4) S5 0.01303(5) 0.01261(5) 0.00987(4) 0.00091(4) 0.00197(3) -0.00066(4) C1 0.01394(18) 0.01068(16) 0.01625(19) -0.00282(14) 0.00284(15) -0.00150(14) C2 0.01515(17) 0.00914(15) 0.01016(15) 0.00051(12) 0.00179(13) -0.00165(13) C3 0.01380(18) 0.01391(18) 0.01295(17) -0.00360(14) 0.00205(14) -0.00049(15) C15 0.01332(16) 0.01010(15) 0.01023(15) 0.00149(12) 0.00302(12) -0.00083(13) C16 0.01253(16) 0.01127(16) 0.00875(14) 0.00082(12) 0.00193(12) -0.00098(12) C17 0.01204(16) 0.00961(15) 0.01044(15) 0.00042(12) 0.00237(12) -0.00141(12) O18 0.02163(18) 0.01249(15) 0.01287(14) 0.00320(11) 0.00525(13) -0.00305(13) Cl19 0.01628(5) 0.01897(6) 0.00862(4) 0.00105(4) 0.00108(3) -0.00287(4) Cl20 0.01538(5) 0.01097(4) 0.01431(5) -0.00118(3) 0.00170(4) -0.00316(3) # 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 S4 C1 1.7467(6) . ? S4 C2 1.7504(5) . ? S5 C3 1.7402(6) . ? S5 C2 1.7488(5) . ? C1 C3 1.3378(8) . ? C1 H6 0.985(11) . ? C2 C2 1.3681(10) 3_665 ? C3 H7 0.963(10) . ? C15 O18 1.2221(6) . ? C15 C16 1.4858(7) . ? C15 C17 1.4856(7) 3_565 ? C16 C17 1.3545(7) . ? C16 Cl19 1.7068(5) . ? C17 C15 1.4856(7) 3_565 ? C17 Cl20 1.7054(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 C1 S4 C2 94.91(3) . . ? C3 S5 C2 94.77(3) . . ? C3 C1 S4 117.16(4) . . ? C3 C1 H6 125.6(6) . . ? S4 C1 H6 117.2(6) . . ? C2 C2 S4 122.26(5) 3_665 . ? C2 C2 S5 122.64(5) 3_665 . ? S4 C2 S5 115.08(3) . . ? C1 C3 S5 118.01(4) . . ? C1 C3 H7 126.2(6) . . ? S5 C3 H7 115.8(6) . . ? O18 C15 C16 121.82(5) . . ? O18 C15 C17 121.85(5) . 3_565 ? C16 C15 C17 116.30(4) . 3_565 ? C17 C16 C15 121.46(4) . . ? C17 C16 Cl19 122.44(4) . . ? C15 C16 Cl19 116.06(4) . . ? C16 C17 C15 122.17(5) . 3_565 ? C16 C17 Cl20 121.88(4) . . ? C15 C17 Cl20 115.95(4) 3_565 . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 53.92 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.126 _refine_diff_density_min -0.107 _refine_diff_density_rms 0.032 #===END #============================================================================== # TTF-CA 15K #============================================================================== data_ttf-ca-15k-molly _database_code_depnum_ccdc_archive 'CCDC 612478' _audit_creation_method SHELXL-97 # CHEMICAL DATA _chemical_name_systematic ; tetrathiafulvalene-p-chloranil ; _chemical_name_common tetrathiafulvalene-p-chloranil _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 S4, C6 Cl4 O2' _chemical_formula_sum 'C12 H4 Cl4 O2 S4' _chemical_formula_weight 450.19 # CRYSTAL DATA 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' Cl Cl 0.1484 0.1585 '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' # CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P n ' _symmetry_space_group_name_Hall 'p_-2yabc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' # These symmetry equivalent positions were chosen instead of # 'x,y,z' and 'x+1/2, -y, z+1/2' (corresponding to Pn space group) # due to the origin choise, obtained by fixing the x and the z coordinates # of CL19 atom. _cell_length_a 7.1999(10) _cell_length_b 7.5556(9) _cell_length_c 14.4798(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.511(10) _cell_angle_gamma 90.00 _cell_volume 779.02(15) _cell_formula_units_Z 2 _cell_measurement_temperature 15(2) _cell_measurement_reflns_used 15990 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 55.47 _exptl_crystal_description prismatic _exptl_crystal_colour black _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.295 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.715 _exptl_absorpt_correction_T_max 0.882 _exptl_absorpt_process_details ; 'de Titta, 1985' ; # EXPERIMENTAL DATA _exptl_special_details ; TTF-CA complex undergoes a structural phase transition at 81K, characterized by a symmetry breaking: in the low temperature phase the molecules do not lye on invertion centers. However they remain almost centrosymmetric. This phase transition has been carefully studied by the temperature evolution of the cell parameters. ; _diffrn_ambient_temperature 15(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 'Xcalibur-Oxford Diffraction' _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15990 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 55.47 _reflns_number_total 15990 _reflns_number_gt 11646 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'MOLLY (Hansen and Coppens,1978)' _computing_molecular_graphics 'ORTEP (L. Farrugia, 1997) ' _computing_publication_material 'WingX (L. Farrugia, 1999)' # REFINEMENT DATA _refine_special_details ; Reflections were merged with Sortav (Blessing, 1995). Multipolar refinement using Hansen and Coppens model (N. Hansen and P. Coppens, Acta Cryst.,2,65 (1978). ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/sig^2' _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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(6) _refine_ls_number_reflns 11646 _refine_ls_number_parameters 424 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0152 _refine_ls_wR_factor_ref 0.0201 _refine_ls_wR_factor_gt 0.0138 _refine_ls_goodness_of_fit_ref 0.75 _refine_ls_restrained_S_all 1.22 _refine_ls_shift/su_max 0.10 _refine_ls_shift/su_mean 0.01 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 S4 S 0.39783(7) 0.23226(8) 0.01935(4) 0.00566(7) Uani 1 1 d . . . S5 S 0.45123(7) 0.43992(8) -0.14656(4) 0.00533(7) Uani 1 1 d . . . C1 C 0.3153(3) 0.1395(3) -0.08975(17) 0.0066(3) Uani 1 1 d . . . H6 H 0.256(8) 0.018(9) -0.092(5) 0.020(12) Uiso 1 1 d . . . C2 C 0.4797(3) 0.4272(3) -0.02500(15) 0.0054(2) Uani 1 1 d . . . C3 C 0.3404(3) 0.2356(3) -0.16537(17) 0.0066(3) Uani 1 1 d . . . H7 H 0.306(7) 0.192(8) -0.233(4) 0.010(10) Uiso 1 1 d . . . C15 C 0.0394(3) 0.6422(3) -0.06197(15) 0.0051(2) Uani 1 1 d . . . C16 C -0.0480(3) 0.4733(3) -0.09730(15) 0.0051(2) Uani 1 1 d . . . C17 C -0.0885(3) 0.3423(3) -0.03837(15) 0.0049(2) Uani 1 1 d . . . O18 O 0.0897(2) 0.7560(3) -0.11457(12) 0.0072(2) Uani 1 1 d . . . Cl19 Cl -0.08286(0) 0.44591(8) -0.21671(0) 0.00600(7) Uani 1 1 d . . . Cl20 Cl -0.17235(6) 0.14031(7) -0.08017(4) 0.00569(7) Uani 1 1 d . . . S11 S 0.63297(7) 0.76068(8) -0.01157(4) 0.00531(7) Uani 1 1 d . . . S12 S 0.56337(7) 0.55644(8) 0.15374(4) 0.00520(7) Uani 1 1 d . . . C8 C 0.6976(3) 0.8588(3) 0.09768(17) 0.0066(3) Uani 1 1 d . . . H13 H 0.752(8) 0.986(9) 0.097(5) 0.016(12) Uiso 1 1 d . . . C9 C 0.5561(3) 0.5637(3) 0.03256(15) 0.0055(2) Uani 1 1 d . . . C10 C 0.6672(3) 0.7637(3) 0.17282(16) 0.0065(3) Uani 1 1 d . . . H14 H 0.696(7) 0.797(9) 0.243(4) 0.020(13) Uiso 1 1 d . . . C21 C -0.0582(3) 0.3627(3) 0.06447(14) 0.0051(2) Uani 1 1 d . . . C22 C 0.0340(3) 0.5298(3) 0.09988(15) 0.0052(2) Uani 1 1 d . . . C23 C 0.0745(3) 0.6610(3) 0.04109(15) 0.0052(2) Uani 1 1 d . . . O24 O -0.1061(2) 0.2486(3) 0.11756(12) 0.0069(2) Uani 1 1 d . . . Cl25 Cl 0.08514(6) 0.54952(8) 0.21932(4) 0.00606(7) Uani 1 1 d . . . Cl26 Cl 0.17124(6) 0.85787(8) 0.08351(4) 0.00594(7) Uani 1 1 d . . . _atom_sites_special_details ; coordinates x and z of chlorine atom Cl19 have been fixed to those of the 105K structure in order to compare both structures. ; 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 S4 0.00703(15) 0.00483(16) 0.00521(16) 0.00029(13) 0.00121(11) -0.00094(12) S5 0.00581(15) 0.00567(19) 0.00450(18) 0.00032(14) 0.00073(12) -0.00058(12) C1 0.0078(6) 0.0052(6) 0.0069(7) -0.0008(5) 0.0014(5) -0.0013(5) C2 0.0067(5) 0.0046(5) 0.0049(5) -0.0001(4) 0.0007(4) -0.0013(4) C3 0.0073(6) 0.0064(7) 0.0060(6) -0.0013(5) 0.0003(4) -0.0010(5) C15 0.0053(5) 0.0050(6) 0.0051(6) 0.0000(4) 0.0015(4) -0.0009(4) C16 0.0060(5) 0.0052(6) 0.0043(5) -0.0006(4) 0.0011(4) -0.0010(4) C17 0.0059(5) 0.0046(6) 0.0043(6) -0.0001(4) 0.0011(4) -0.0010(4) O18 0.0098(5) 0.0060(5) 0.0060(5) 0.0009(4) 0.0022(4) -0.0022(4) Cl19 0.00693(14) 0.00707(17) 0.00398(15) 0.00007(13) 0.00074(11) -0.00097(12) Cl20 0.00661(14) 0.00470(16) 0.00573(16) -0.00055(13) 0.00081(11) -0.00102(11) S11 0.00661(14) 0.00454(16) 0.00481(16) 0.00045(12) 0.00094(11) -0.00072(12) S12 0.00587(15) 0.00537(18) 0.00447(17) 0.00015(14) 0.00114(12) -0.00037(12) C8 0.0076(6) 0.0061(7) 0.0061(7) -0.0008(5) 0.0011(4) -0.0009(5) C9 0.0069(5) 0.0051(6) 0.0047(5) 0.0000(4) 0.0011(4) -0.0012(4) C10 0.0079(6) 0.0062(7) 0.0053(6) -0.0013(5) 0.0011(4) -0.0007(5) C21 0.0064(5) 0.0047(6) 0.0041(5) 0.0005(4) 0.0007(4) -0.0009(4) C22 0.0060(5) 0.0054(6) 0.0044(5) 0.0003(4) 0.0009(4) -0.0007(4) C23 0.0055(5) 0.0050(6) 0.0049(6) 0.0002(4) 0.0005(4) -0.0011(4) O24 0.0097(5) 0.0062(5) 0.0051(5) 0.0013(4) 0.0015(4) -0.0017(4) Cl25 0.00701(14) 0.00716(17) 0.00388(15) 0.00013(13) 0.00038(11) -0.00080(12) Cl26 0.00673(14) 0.00509(16) 0.00592(16) -0.00053(13) 0.00068(11) -0.00140(11) # 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 S4 C2 1.744(2) . ? S4 C1 1.750(2) . ? S5 C3 1.741(2) . ? S5 C2 1.744(2) . ? C1 C3 1.348(3) . ? C1 H6 1.01(7) . ? C2 C9 1.388(2) . ? C3 H7 1.03(6) . ? C15 O18 1.238(3) . ? C15 C16 1.480(3) . ? C15 C23 1.483(3) . ? C16 C17 1.367(3) . ? C16 Cl19 1.723(2) . ? C17 C21 1.481(3) . ? C17 Cl20 1.718(2) . ? S11 C9 1.742(2) . ? S11 C8 1.747(2) . ? S12 C10 1.739(2) . ? S12 C9 1.749(2) . ? C8 C10 1.349(4) . ? C8 H13 1.04(7) . ? C10 H14 1.03(6) . ? C21 O24 1.238(3) . ? C21 C22 1.482(3) . ? C22 C23 1.366(3) . ? C22 Cl25 1.721(2) . ? C23 Cl26 1.717(2) . ? 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 C2 S4 C1 95.39(11) . . ? C3 S5 C2 95.25(11) . . ? C3 C1 S4 116.69(17) . . ? C3 C1 H6 125(4) . . ? S4 C1 H6 119(4) . . ? C9 C2 S4 122.15(12) . . ? C9 C2 S5 122.81(13) . . ? S4 C2 S5 115.00(12) . . ? C1 C3 S5 117.65(18) . . ? C1 C3 H7 124(3) . . ? S5 C3 H7 118(3) . . ? O18 C15 C16 122.3(2) . . ? O18 C15 C23 122.08(19) . . ? C16 C15 C23 115.52(18) . . ? C17 C16 C15 121.87(19) . . ? C17 C16 Cl19 121.78(16) . . ? C15 C16 Cl19 116.25(16) . . ? C16 C17 C21 122.61(19) . . ? C16 C17 Cl20 121.34(17) . . ? C21 C17 Cl20 116.03(16) . . ? C9 S11 C8 94.99(11) . . ? C10 S12 C9 94.56(11) . . ? C10 C8 S11 116.81(18) . . ? C10 C8 H13 127(4) . . ? S11 C8 H13 116(4) . . ? C2 C9 S11 122.28(12) . . ? C2 C9 S12 121.99(12) . . ? S11 C9 S12 115.52(12) . . ? C8 C10 S12 117.96(18) . . ? C8 C10 H14 129(4) . . ? S12 C10 H14 113(4) . . ? O24 C21 C22 122.02(19) . . ? O24 C21 C17 122.59(19) . . ? C22 C21 C17 115.39(18) . . ? C23 C22 C21 121.89(19) . . ? C23 C22 Cl25 122.01(17) . . ? C21 C22 Cl25 116.10(15) . . ? C22 C23 C15 122.52(19) . . ? C22 C23 Cl26 121.23(17) . . ? C15 C23 Cl26 116.26(16) . . ? _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 55.47 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.137 _refine_diff_density_min -0.20 _refine_diff_density_rms 0.042 #===END #============================================================================== # TTF 100K #============================================================================== data_ttf _database_code_depnum_ccdc_archive 'CCDC 614385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrathiafulvalene ; _chemical_name_common Tetrathiafulvalene _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 S4' _chemical_formula_sum 'C6 H4 S4' _chemical_formula_weight 204.33 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3101(3) _cell_length_b 12.7800(3) _cell_length_c 7.95820(10) _cell_angle_alpha 99.627(3) _cell_angle_beta 95.906(3) _cell_angle_gamma 101.083(3) _cell_volume 809.74(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6959 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 35.78 _cell_special_details ; The axial order is not standar, but correspond to the structure reported by Ellern. A. Ellern, Chem. Matter. 6, 1378 (1994).' ; _exptl_crystal_description prismatic _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 1.087 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details 'de Titta, 1985' _diffrn_ambient_temperature 100(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 'Xcalibur-Oxford Diffraction' _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6959 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0978 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 35.78 _reflns_number_total 6959 _reflns_number_gt 4893 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'MOLLY (Hansen and Coppens, 1978)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997' _computing_publication_material 'WingX (Farrugia, 1999)' _refine_special_details ; Reflections were merged by SORTAV program (Blessing, 1995). Multipolar refinement has been performed using Hansen and Coppens model (N. Hansen and P. Coppens, Acta Cryst. 2, 65 (1978)' ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/sig^2' _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 6959 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0142 _refine_ls_wR_factor_ref 0.0190 _refine_ls_wR_factor_gt 0.0112 _refine_ls_goodness_of_fit_ref 0.9 _refine_ls_restrained_S_all 0.82 _refine_ls_shift/su_max 0.1 _refine_ls_shift/su_mean 0.02 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 C11 C 0.96630(9) 0.47644(6) 0.06112(10) 0.01600(13) Uani 1 1 d . . . S11 S 0.94046(3) 0.336119(16) 0.05998(3) 0.01993(4) Uani 1 1 d . . . S12 S 0.89514(3) 0.550060(18) 0.23534(3) 0.02165(4) Uani 1 1 d . . . C12 C 0.86608(11) 0.34356(7) 0.25751(12) 0.02260(17) Uani 1 1 d . . . H12 H 0.8468(13) 0.2832(9) 0.3019(14) 0.026(3) Uiso 1 1 d . . . C13 C 0.84581(11) 0.43905(8) 0.33615(12) 0.02298(17) Uani 1 1 d . . . H13 H 0.8103(13) 0.4514(9) 0.4377(15) 0.029(3) Uiso 1 1 d . . . C21 C 0.50043(9) 0.53320(6) 0.44272(10) 0.01651(14) Uani 1 1 d . . . S21 S 0.38053(3) 0.494704(19) 0.23822(3) 0.02583(5) Uani 1 1 d . . . S22 S 0.61992(3) 0.666623(17) 0.48640(3) 0.02307(5) Uani 1 1 d . . . C22 C 0.45386(11) 0.61645(8) 0.17239(13) 0.02267(17) Uani 1 1 d . . . H22 H 0.4140(14) 0.6225(9) 0.0659(15) 0.034(3) Uiso 1 1 d . . . C23 C 0.56125(11) 0.69337(7) 0.28368(12) 0.02221(16) Uani 1 1 d . . . H23 H 0.6058(14) 0.7563(9) 0.2613(15) 0.034(3) Uiso 1 1 d . . . C31 C 0.94376(9) 0.02658(6) 0.53059(11) 0.01621(13) Uani 1 1 d . . . S31 S 0.96970(3) 0.168747(17) 0.55982(3) 0.02030(4) Uani 1 1 d . . . S32 S 0.75958(3) -0.040170(18) 0.59214(3) 0.02246(4) Uani 1 1 d . . . C32 C 0.77672(12) 0.17099(8) 0.62695(13) 0.02540(18) Uani 1 1 d . . . H32 H 0.7486(14) 0.2346(9) 0.6492(15) 0.030(3) Uiso 1 1 d . . . C33 C 0.68279(12) 0.07728(8) 0.64141(13) 0.02581(18) Uani 1 1 d . . . H33 H 0.5794(14) 0.0668(9) 0.6746(15) 0.035(3) Uiso 1 1 d . . . C41 C 0.55905(9) -0.02920(6) 1.00129(10) 0.01609(13) Uani 1 1 d . . . S41 S 0.52767(3) -0.163817(17) 0.88785(3) 0.02184(4) Uani 1 1 d . . . S42 S 0.75828(3) 0.022743(19) 1.11787(3) 0.02425(5) Uani 1 1 d . . . C42 C 0.72869(11) -0.17802(7) 0.95014(12) 0.02220(16) Uani 1 1 d . . . H42 H 0.7541(14) -0.2401(9) 0.9101(15) 0.031(3) Uiso 1 1 d . . . C43 C 0.83183(11) -0.09473(8) 1.05334(12) 0.02155(16) Uani 1 1 d . . . H43 H 0.9384(13) -0.0932(9) 1.0941(14) 0.028(3) Uiso 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 C11 0.0168(3) 0.0130(3) 0.0182(4) 0.0013(3) 0.0008(3) 0.0055(2) S11 0.02405(9) 0.01313(8) 0.02295(10) 0.00330(7) 0.00219(8) 0.00552(7) S12 0.02763(10) 0.01751(9) 0.02180(11) 0.00248(8) 0.00810(8) 0.00834(8) C12 0.0231(4) 0.0209(4) 0.0237(4) 0.0090(3) 0.0013(3) 0.0014(3) C13 0.0229(4) 0.0263(4) 0.0208(4) 0.0072(3) 0.0057(3) 0.0041(3) C21 0.0162(3) 0.0152(3) 0.0156(3) -0.0009(3) 0.0033(3) 0.0001(2) S21 0.02826(11) 0.02428(11) 0.01863(10) 0.00313(8) -0.00357(8) -0.00536(8) S22 0.03005(11) 0.01612(9) 0.01805(10) 0.00057(7) 0.00331(8) -0.00486(8) C22 0.0222(4) 0.0256(4) 0.0224(4) 0.0081(3) 0.0033(3) 0.0074(3) C23 0.0255(4) 0.0186(4) 0.0250(4) 0.0075(3) 0.0069(3) 0.0060(3) C31 0.0167(3) 0.0129(3) 0.0178(4) 0.0051(3) -0.0008(3) 0.0002(2) S31 0.02140(9) 0.01296(8) 0.02570(11) 0.00496(7) -0.00034(8) 0.00247(7) S32 0.01963(9) 0.01946(9) 0.02830(12) 0.00788(8) 0.00515(8) 0.00036(7) C32 0.0294(4) 0.0222(4) 0.0247(5) 0.0000(3) 0.0042(3) 0.0094(3) C33 0.0243(4) 0.0293(5) 0.0246(5) 0.0025(4) 0.0079(3) 0.0074(3) C41 0.0155(3) 0.0166(3) 0.0150(3) 0.0015(3) 0.0028(3) 0.0016(2) S41 0.01797(9) 0.01752(9) 0.02712(11) -0.00196(8) 0.00239(8) 0.00250(7) S42 0.01691(9) 0.02477(11) 0.02648(12) -0.00370(9) -0.00320(8) 0.00402(7) C42 0.0239(4) 0.0209(4) 0.0248(4) 0.0069(3) 0.0046(3) 0.0092(3) C43 0.0197(4) 0.0269(4) 0.0209(4) 0.0082(3) 0.0025(3) 0.0091(3) _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 C11 C11 1.3419(16) 2_765 ? C11 S12 1.7617(8) . ? C11 S11 1.7631(8) . ? S11 C12 1.7421(10) . ? S12 C13 1.7461(9) . ? C12 C13 1.3246(13) . ? C12 H12 0.895(11) . ? C13 H13 0.888(11) . ? C21 C21 1.3450(16) 2_666 ? C21 S21 1.7588(8) . ? C21 S22 1.7591(8) . ? S21 C22 1.7437(9) . ? S22 C23 1.7447(10) . ? C22 C23 1.3252(13) . ? C22 H22 0.899(11) . ? C23 H23 0.873(11) . ? C31 C31 1.3414(16) 2_756 ? C31 S32 1.7613(8) . ? C31 S31 1.7606(8) . ? S31 C32 1.7455(10) . ? S32 C33 1.7427(10) . ? C32 C33 1.3274(14) . ? C32 H32 0.883(11) . ? C33 H33 0.917(11) . ? C41 C41 1.3428(16) 2_657 ? C41 S42 1.7601(8) . ? C41 S41 1.7614(8) . ? S41 C42 1.7451(9) . ? S42 C43 1.7466(9) . ? C42 C43 1.3244(13) . ? C42 H42 0.877(11) . ? C43 H43 0.906(11) . ? 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 C11 C11 S12 122.55(8) 2_765 . ? C11 C11 S11 122.90(8) 2_765 . ? S12 C11 S11 114.55(4) . . ? C12 S11 C11 94.56(4) . . ? C13 S12 C11 94.53(4) . . ? C13 C12 S11 118.14(7) . . ? C13 C12 H12 123.6(7) . . ? S11 C12 H12 118.2(7) . . ? C12 C13 S12 117.97(7) . . ? C12 C13 H13 124.9(7) . . ? S12 C13 H13 117.1(7) . . ? C21 C21 S21 122.94(8) 2_666 . ? C21 C21 S22 122.64(8) 2_666 . ? S21 C21 S22 114.42(5) . . ? C22 S21 C21 94.95(4) . . ? C23 S22 C21 94.77(4) . . ? C23 C22 S21 117.74(7) . . ? C23 C22 H22 125.1(7) . . ? S21 C22 H22 117.1(7) . . ? C22 C23 S22 118.05(7) . . ? C22 C23 H23 124.0(8) . . ? S22 C23 H23 117.9(8) . . ? C31 C31 S32 122.63(8) 2_756 . ? C31 C31 S31 122.86(8) 2_756 . ? S32 C31 S31 114.50(5) . . ? C32 S31 C31 94.71(4) . . ? C33 S32 C31 94.72(4) . . ? C33 C32 S31 117.85(8) . . ? C33 C32 H32 124.6(7) . . ? S31 C32 H32 117.5(7) . . ? C32 C33 S32 118.04(8) . . ? C32 C33 H33 126.9(7) . . ? S32 C33 H33 115.1(7) . . ? C41 C41 S42 122.71(8) 2_657 . ? C41 C41 S41 122.81(8) 2_657 . ? S42 C41 S41 114.48(4) . . ? C42 S41 C41 94.78(4) . . ? C43 S42 C41 94.81(4) . . ? C43 C42 S41 118.02(7) . . ? C43 C42 H42 124.7(8) . . ? S41 C42 H42 117.2(8) . . ? C42 C43 S42 117.90(7) . . ? C42 C43 H43 125.6(7) . . ? S42 C43 H43 116.5(7) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 35.78 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.268 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.06 #===END #============================================================================== # CA 100K #============================================================================== data_ca _database_code_depnum_ccdc_archive 'CCDC 614386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; chloranil ; _chemical_name_common chloranil _chemical_melting_point ? _chemical_formula_moiety 'C6 Cl4 O2' _chemical_formula_sum 'C6 Cl4 O2' _chemical_formula_weight 245.86 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5745(8) _cell_length_b 5.6898(5) _cell_length_c 8.7004(8) _cell_angle_alpha 90.000 _cell_angle_beta 105.952(8) _cell_angle_gamma 90.0000 _cell_volume 408.12(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4959 _cell_measurement_theta_min 4.33 _cell_measurement_theta_max 56.48 _exptl_crystal_description Prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 1.395 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.84 _exptl_absorpt_process_details 'de Titta, 1985' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Xcalibur-Oxford Diffraction' _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5445 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 56.48 _reflns_number_total 5445 _reflns_number_gt 2695 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'MOLLY (Hansen and Coppens, 1978)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997' _computing_publication_material 'WingX (Farrugia, 1999)' _refine_special_details ; Reflections were merged by SORTAV program (Blessing, 1995). Multipolar refinement using Hansen and Coppens model (N. Hansen and P. Coppens, Acta Cryst. 2, 65 (1978)' ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/sig^2' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5445 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0167 _refine_ls_wR_factor_ref 0.0162 _refine_ls_wR_factor_gt 0.0137 _refine_ls_goodness_of_fit_ref 0.77 _refine_ls_restrained_S_all 0.617 _refine_ls_shift/su_max 0.05 _refine_ls_shift/su_mean 0.01 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.65672(7) 0.09524(10) 0.58469(6) 0.01398(7) Uani 1 1 d . . . C2 C 0.50286(7) 0.21323(10) 0.59332(6) 0.01329(7) Uani 1 1 d . . . C3 C 0.34614(7) 0.09901(10) 0.50564(6) 0.01389(7) Uani 1 1 d . . . O1 O 0.50504(7) 0.39682(9) 0.66511(6) 0.01979(8) Uani 1 1 d . . . Cl1 Cl 0.83237(2) 0.22373(4) 0.69348(2) 0.02247(4) Uani 1 1 d . . . Cl2 Cl 0.17439(2) 0.22986(4) 0.52709(2) 0.02271(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 C1 0.01473(16) 0.01472(17) 0.01195(14) -0.00075(13) 0.00273(12) -0.00222(14) C2 0.01760(17) 0.01153(16) 0.01074(14) -0.00040(12) 0.00390(12) -0.00083(13) C3 0.01484(16) 0.01440(17) 0.01252(14) 0.00031(13) 0.00392(12) 0.00109(14) O1 0.0304(2) 0.01386(16) 0.01593(15) -0.00445(13) 0.00778(15) -0.00109(16) Cl1 0.01877(6) 0.02649(8) 0.01981(6) -0.00280(5) 0.00136(5) -0.00855(5) Cl2 0.01881(6) 0.02601(8) 0.02420(7) 0.00149(6) 0.00739(5) 0.00739(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.3525(8) 3_656 ? C1 C2 1.5005(8) . ? C1 Cl1 1.7074(6) . ? C2 O1 1.2145(7) . ? C2 C3 1.4989(8) . ? C3 C1 1.3525(8) 3_656 ? C3 Cl2 1.7055(6) . ? 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 C1 C2 121.26(5) 3_656 . ? C3 C1 Cl1 122.98(5) 3_656 . ? C2 C1 Cl1 115.75(4) . . ? O1 C2 C3 121.31(6) . . ? O1 C2 C1 121.40(5) . . ? C3 C2 C1 117.27(5) . . ? C1 C3 C2 121.38(5) 3_656 . ? C1 C3 Cl2 122.82(5) 3_656 . ? C2 C3 Cl2 115.81(4) . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 56.48 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.214 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.041