# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Narcis Avarvari' _publ_contact_author_email NARCIS.AVARVARI@UNIV-ANGERS.FR _publ_section_title ; C2-Symmetric chiral tetrathiafulvalene-bis(oxazolines) (TTF-BOX): new precursors for organic materials and electroactive metal complexes ; loop_ _publ_author_name 'Narcis Avarvari' 'Francois Riobe' # Attachment '3a_revised.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 718616' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (S)-EDT-TTF-bis(Me-Ox) _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N2 O2 S6' _chemical_formula_sum 'C16 H16 N2 O2 S6' _chemical_formula_weight 460.67 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.0250(3) _cell_length_b 17.6060(12) _cell_length_c 11.9010(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.87(2) _cell_angle_gamma 90.00 _cell_volume 1030.37(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 74 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.783812 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _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 13665 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3807 _reflns_number_gt 2687 _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^)+(0.0386P)^2^+0.0070P] 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_abs_structure_details ? _chemical_absolute_configuration syn _refine_ls_abs_structure_Flack -0.06(8) _refine_ls_number_reflns 3807 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1212(6) 0.03700(18) 0.0833(3) 0.0446(8) Uani 1 1 d . . . C2 C 0.5067(7) 0.10501(19) 0.2241(3) 0.0493(8) Uani 1 1 d . . . C3 C 0.6827(7) 0.15697(19) 0.2792(3) 0.0483(8) Uani 1 1 d . . . C4 C 0.9408(7) 0.2823(2) 0.3386(3) 0.0486(9) Uani 1 1 d . . . C5A C 1.284(3) 0.3922(11) 0.4609(14) 0.079(4) Uani 0.50 1 d P . . H5A1 H 1.4546 0.3872 0.4357 0.095 Uiso 0.50 1 calc PR . . H5A2 H 1.2749 0.4435 0.4895 0.095 Uiso 0.50 1 calc PR . . C5B C 1.166(2) 0.3930(10) 0.4878(14) 0.064(4) Uani 0.50 1 d P . . H5B1 H 1.2160 0.4458 0.5029 0.077 Uiso 0.50 1 calc PR . . H5B2 H 1.0417 0.3783 0.5365 0.077 Uiso 0.50 1 calc PR . . C6A C 1.428(2) 0.3407(6) 0.5124(10) 0.070(3) Uani 0.50 1 d P . . H6A1 H 1.5395 0.3553 0.5859 0.084 Uiso 0.50 1 calc PR . . H6A2 H 1.5331 0.3507 0.4541 0.084 Uiso 0.50 1 calc PR . . C6B C 1.286(3) 0.3400(5) 0.5547(8) 0.070(3) Uani 0.50 1 d P . . H6B1 H 1.1092 0.3402 0.5755 0.085 Uiso 0.50 1 calc PR . . H6B2 H 1.4197 0.3565 0.6211 0.085 Uiso 0.50 1 calc PR . . C7 C 1.0799(7) 0.2291(2) 0.4070(3) 0.0494(9) Uani 1 1 d . . . C8 C 0.2540(7) -0.01863(18) 0.1490(3) 0.0482(9) Uani 1 1 d . . . C9 C -0.1151(7) 0.03064(19) -0.0101(3) 0.0501(8) Uani 1 1 d . . . C10 C -0.4419(7) 0.0528(2) -0.1588(3) 0.0674(10) Uani 1 1 d . . . H10 H -0.5976 0.0811 -0.1424 0.081 Uiso 1 1 calc R . . C11 C -0.4591(8) -0.0286(2) -0.1221(3) 0.0649(10) Uani 1 1 d . . . H11A H -0.6415 -0.0409 -0.1129 0.078 Uiso 1 1 calc R . . H11B H -0.4085 -0.0630 -0.1778 0.078 Uiso 1 1 calc R . . C12 C -0.4319(11) 0.0620(3) -0.2850(3) 0.1024(16) Uani 1 1 d . . . H12A H -0.4181 0.1150 -0.3023 0.154 Uiso 1 1 calc R . . H12B H -0.5947 0.0414 -0.3316 0.154 Uiso 1 1 calc R . . H12C H -0.2767 0.0355 -0.3007 0.154 Uiso 1 1 calc R . . C13 C 0.2005(6) -0.10058(19) 0.1386(3) 0.0484(9) Uani 1 1 d . . . C14 C 0.1237(7) -0.22107(19) 0.1681(4) 0.0609(10) Uani 1 1 d . . . H14 H 0.2806 -0.2538 0.1968 0.073 Uiso 1 1 calc R . . C15 C 0.1004(11) -0.2085(2) 0.0422(4) 0.0891(15) Uani 1 1 d . . . H15A H 0.2189 -0.2429 0.0118 0.107 Uiso 1 1 calc R . . H15B H -0.0852 -0.2163 0.0010 0.107 Uiso 1 1 calc R . . C16 C -0.1213(10) -0.2548(3) 0.1987(5) 0.120(2) Uani 1 1 d . . . H16A H -0.0902 -0.2622 0.2803 0.180 Uiso 1 1 calc R . . H16B H -0.1594 -0.3029 0.1606 0.180 Uiso 1 1 calc R . . H16C H -0.2732 -0.2213 0.1751 0.180 Uiso 1 1 calc R . . O1 O -0.2687(5) -0.03312(16) -0.0141(2) 0.0771(8) Uani 1 1 d . . . O2 O 0.1833(6) -0.12975(14) 0.0322(2) 0.0816(8) Uani 1 1 d . . . N1 N -0.1902(6) 0.08095(16) -0.0842(3) 0.0619(8) Uani 1 1 d . . . N2 N 0.1778(6) -0.14421(16) 0.2182(2) 0.0573(7) Uani 1 1 d . . . S1 S 0.64573(19) 0.25409(5) 0.24235(8) 0.0557(3) Uani 1 1 d . . . S2 S 0.2362(2) 0.13048(5) 0.11207(8) 0.0596(3) Uani 1 1 d . . . S3 S 0.9492(2) 0.13630(5) 0.39474(9) 0.0637(3) Uani 1 1 d . . . S4 S 0.5233(2) 0.00810(5) 0.25944(8) 0.0644(3) Uani 1 1 d . . . S5 S 1.36778(19) 0.24309(6) 0.51514(9) 0.0696(3) Uani 1 1 d . . . S6 S 1.0076(2) 0.37966(6) 0.33712(9) 0.0758(3) 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 0.0481(19) 0.037(2) 0.0454(19) 0.0009(16) 0.0024(16) -0.0032(15) C2 0.060(2) 0.037(2) 0.046(2) 0.0015(16) 0.0003(17) -0.0008(18) C3 0.062(2) 0.0330(19) 0.0460(19) -0.0008(16) 0.0007(18) -0.0028(17) C4 0.054(2) 0.045(2) 0.0424(19) 0.0046(16) -0.0013(17) -0.0108(17) C5A 0.072(11) 0.078(8) 0.075(10) -0.014(7) -0.012(7) -0.012(9) C5B 0.060(9) 0.063(7) 0.065(8) -0.014(6) 0.002(6) -0.004(7) C6A 0.069(7) 0.084(8) 0.047(6) -0.006(5) -0.009(5) -0.014(6) C6B 0.098(8) 0.054(6) 0.050(6) -0.013(5) -0.007(6) -0.011(6) C7 0.0516(19) 0.051(2) 0.041(2) -0.0020(17) 0.0002(17) -0.0051(17) C8 0.055(2) 0.038(2) 0.048(2) -0.0045(16) 0.0019(17) -0.0058(16) C9 0.057(2) 0.040(2) 0.053(2) -0.0024(17) 0.0082(18) -0.0011(18) C10 0.057(2) 0.060(3) 0.073(3) -0.015(2) -0.016(2) 0.018(2) C11 0.059(2) 0.076(3) 0.053(2) -0.004(2) -0.003(2) -0.016(2) C12 0.154(4) 0.062(3) 0.070(3) 0.009(2) -0.026(3) -0.012(3) C13 0.0462(19) 0.040(2) 0.056(2) -0.0036(18) 0.0028(17) -0.0041(16) C14 0.060(2) 0.034(2) 0.092(3) -0.0030(19) 0.023(2) -0.0060(17) C15 0.135(4) 0.052(3) 0.086(3) -0.025(2) 0.037(3) -0.030(3) C16 0.121(4) 0.087(4) 0.180(5) -0.046(4) 0.097(4) -0.051(3) O1 0.0780(18) 0.076(2) 0.0655(17) 0.0129(14) -0.0136(15) -0.0328(16) O2 0.140(2) 0.0493(16) 0.0629(16) -0.0171(14) 0.0383(16) -0.0351(16) N1 0.066(2) 0.0388(18) 0.068(2) -0.0028(16) -0.0155(17) 0.0016(14) N2 0.0675(19) 0.0396(17) 0.0581(18) 0.0050(15) -0.0025(15) -0.0070(14) S1 0.0651(5) 0.0379(5) 0.0524(6) 0.0036(4) -0.0150(5) -0.0059(4) S2 0.0725(7) 0.0342(5) 0.0595(6) 0.0021(5) -0.0154(5) -0.0011(5) S3 0.0752(7) 0.0440(6) 0.0597(6) 0.0065(5) -0.0149(5) -0.0005(5) S4 0.0822(7) 0.0356(5) 0.0603(6) 0.0051(4) -0.0201(5) -0.0033(5) S5 0.0600(6) 0.0753(8) 0.0614(6) 0.0032(6) -0.0155(5) -0.0015(5) S6 0.0853(8) 0.0502(6) 0.0747(6) 0.0117(5) -0.0238(5) -0.0232(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 C8 1.342(4) . ? C1 C9 1.454(4) . ? C1 S2 1.754(3) . ? C2 C3 1.346(4) . ? C2 S4 1.755(3) . ? C2 S2 1.755(3) . ? C3 S3 1.749(4) . ? C3 S1 1.766(3) . ? C4 C7 1.339(5) . ? C4 S6 1.748(4) . ? C4 S1 1.749(3) . ? C5A C6B 1.44(2) . ? C5A S6 1.817(16) . ? C5B C6A 1.585(18) . ? C5B S6 1.822(16) . ? C6A S5 1.746(11) . ? C6B S5 1.839(11) . ? C7 S5 1.744(3) . ? C7 S3 1.756(4) . ? C8 C13 1.468(5) . ? C8 S4 1.746(3) . ? C9 N1 1.253(4) . ? C9 O1 1.358(4) . ? C10 N1 1.473(4) . ? C10 C11 1.506(6) . ? C10 C12 1.522(5) . ? C11 O1 1.438(4) . ? C13 N2 1.243(4) . ? C13 O2 1.352(4) . ? C14 C16 1.478(5) . ? C14 N2 1.481(4) . ? C14 C15 1.495(5) . ? C15 O2 1.460(4) . ? 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 C8 C1 C9 128.2(3) . . ? C8 C1 S2 117.8(2) . . ? C9 C1 S2 113.9(2) . . ? C3 C2 S4 123.4(3) . . ? C3 C2 S2 121.7(3) . . ? S4 C2 S2 114.9(2) . . ? C2 C3 S3 124.2(3) . . ? C2 C3 S1 120.8(3) . . ? S3 C3 S1 114.93(19) . . ? C7 C4 S6 127.9(3) . . ? C7 C4 S1 117.8(3) . . ? S6 C4 S1 114.24(19) . . ? C6B C5A S6 115.7(11) . . ? C6A C5B S6 106.6(8) . . ? C5B C6A S5 115.7(9) . . ? C5A C6B S5 111.0(10) . . ? C4 C7 S5 126.9(3) . . ? C4 C7 S3 117.4(2) . . ? S5 C7 S3 115.6(2) . . ? C1 C8 C13 127.4(3) . . ? C1 C8 S4 117.2(2) . . ? C13 C8 S4 115.4(2) . . ? N1 C9 O1 118.2(3) . . ? N1 C9 C1 124.4(3) . . ? O1 C9 C1 117.4(3) . . ? N1 C10 C11 103.8(3) . . ? N1 C10 C12 111.1(4) . . ? C11 C10 C12 113.7(3) . . ? O1 C11 C10 104.1(3) . . ? N2 C13 O2 118.7(3) . . ? N2 C13 C8 125.9(3) . . ? O2 C13 C8 115.3(3) . . ? C16 C14 N2 111.2(3) . . ? C16 C14 C15 114.1(4) . . ? N2 C14 C15 103.8(3) . . ? O2 C15 C14 104.9(3) . . ? C9 O1 C11 104.8(3) . . ? C13 O2 C15 104.4(3) . . ? C9 N1 C10 106.5(3) . . ? C13 N2 C14 107.2(3) . . ? C4 S1 C3 94.61(16) . . ? C1 S2 C2 94.64(16) . . ? C3 S3 C7 94.85(17) . . ? C8 S4 C2 95.19(16) . . ? C7 S5 C6A 104.3(4) . . ? C7 S5 C6B 97.1(4) . . ? C6A S5 C6B 30.8(3) . . ? C4 S6 C5A 103.1(6) . . ? C4 S6 C5B 99.3(6) . . ? C5A S6 C5B 23.1(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.211 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.045 # Attachment '4a_revised.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 718617' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ((S)-EDT-TTF-bis(Me-Ox))Mo(CO)4 _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 Mo N2 O6 S6' _chemical_formula_sum 'C20 H16 Mo N2 O6 S6' _chemical_formula_weight 668.65 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' Mo Mo -1.6832 0.6857 '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 monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9794(9) _cell_length_b 12.1549(9) _cell_length_c 13.5558(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.397(13) _cell_angle_gamma 90.00 _cell_volume 1312.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4878 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.01 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.016 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6959 _exptl_absorpt_correction_T_max 0.8298 _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 'STOE IPDS' _diffrn_measurement_method 'Oscillation Phi Incr 1.1 deg' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10234 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.01 _reflns_number_total 4878 _reflns_number_gt 3963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE, STOE IPDS' _computing_cell_refinement 'SELECT,CELL, STOE IPDS' _computing_data_reduction 'INTEGRATE, STOE IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1e (Crystal Impact GbR 2005)' _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^)+(0.0478P)^2^+0.0395P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration syn _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 4878 _refine_ls_number_parameters 334 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mo1 Mo 0.33524(5) 0.51545(4) 0.95166(3) 0.04331(12) Uani 1 1 d . . . S1 S 0.63846(19) 0.34989(13) 0.67309(12) 0.0592(4) Uani 1 1 d . . . S2 S 0.9666(2) 0.35296(16) 0.54741(14) 0.0777(6) Uani 1 1 d . . . S3 S 1.2940(2) 0.34649(14) 0.45966(13) 0.0629(4) Uani 1 1 d . . . S4 S 1.1699(3) 0.59403(18) 0.35260(19) 0.0994(8) Uani 1 1 d . . . S5 S 0.8651(2) 0.56677(14) 0.46075(12) 0.0621(4) Uani 1 1 d . . . S6 S 0.5539(2) 0.57607(13) 0.60873(12) 0.0606(4) Uani 1 1 d . . . O1 O 0.3374(5) 0.2366(3) 0.7424(3) 0.0528(9) Uani 1 1 d . . . O2 O 0.2017(6) 0.6314(4) 0.6454(3) 0.0688(13) Uani 1 1 d . . . O3 O 0.7108(6) 0.5568(6) 0.9001(5) 0.113(3) Uani 1 1 d . . . O4 O 0.0023(5) 0.5145(6) 1.0666(3) 0.0794(12) Uani 1 1 d . . . O5 O 0.3876(6) 0.7275(5) 1.0783(4) 0.0863(16) Uani 1 1 d . . . O6 O 0.4887(9) 0.3816(7) 1.1306(4) 0.124(3) Uani 1 1 d . . . N1 N 0.2908(5) 0.3634(3) 0.8577(3) 0.0381(9) Uani 1 1 d . . . N2 N 0.2284(5) 0.5916(4) 0.8079(3) 0.0412(9) Uani 1 1 d . . . C1 C 0.4628(6) 0.4100(4) 0.7192(4) 0.0424(11) Uani 1 1 d . . . C2 C 0.6912(7) 0.4643(5) 0.6037(4) 0.0510(13) Uani 1 1 d . . . C3 C 0.8258(7) 0.4637(5) 0.5452(4) 0.0559(15) Uani 1 1 d . . . C4 C 1.1093(6) 0.4181(5) 0.4742(4) 0.0472(13) Uani 1 1 d . . . C5A C 1.384(3) 0.431(3) 0.357(3) 0.110(15) Uani 0.50 1 d P . . H5A1 H 1.4709 0.4780 0.3875 0.133 Uiso 0.50 1 calc PR . . H5A2 H 1.4389 0.3805 0.3142 0.133 Uiso 0.50 1 calc PR . . C5B C 1.364(5) 0.397(3) 0.357(3) 0.109(14) Uani 0.50 1 d P . . H5B1 H 1.4792 0.3724 0.3525 0.131 Uiso 0.50 1 calc PR . . H5B2 H 1.2989 0.3644 0.3016 0.131 Uiso 0.50 1 calc PR . . C6A C 1.3606(19) 0.5268(18) 0.3429(14) 0.070(4) Uani 0.50 1 d P . . H6A1 H 1.4004 0.5432 0.2783 0.084 Uiso 0.50 1 calc PR . . H6A2 H 1.4407 0.5584 0.3916 0.084 Uiso 0.50 1 calc PR . . C6B C 1.285(3) 0.494(2) 0.3001(11) 0.091(7) Uani 0.50 1 d P . . H6B1 H 1.2076 0.4467 0.2626 0.110 Uiso 0.50 1 calc PR . . H6B2 H 1.3544 0.5300 0.2531 0.110 Uiso 0.50 1 calc PR . . C7 C 1.0609(6) 0.5156(7) 0.4333(4) 0.0533(12) Uani 1 1 d . . . C8 C 0.4244(5) 0.5136(6) 0.6920(3) 0.0431(10) Uani 1 1 d . . . C9 C 0.3600(6) 0.3387(4) 0.7784(3) 0.0394(11) Uani 1 1 d . . . C10 C 0.1844(6) 0.2684(4) 0.8821(4) 0.0452(13) Uani 1 1 d . . . H10 H 0.2032 0.2485 0.9519 0.054 Uiso 1 1 calc R . . C11 C 0.2458(8) 0.1776(5) 0.8163(4) 0.0573(15) Uani 1 1 d . . . H11A H 0.3190 0.1270 0.8538 0.069 Uiso 1 1 calc R . . H11B H 0.1523 0.1368 0.7855 0.069 Uiso 1 1 calc R . . C12 C 0.0036(8) 0.2969(6) 0.8588(5) 0.0643(18) Uani 1 1 d . . . H12A H -0.0289 0.3549 0.9018 0.096 Uiso 1 1 calc R . . H12B H -0.0649 0.2333 0.8685 0.096 Uiso 1 1 calc R . . H12C H -0.0113 0.3207 0.7914 0.096 Uiso 1 1 calc R . . C13 C 0.2812(6) 0.5786(5) 0.7205(3) 0.0428(11) Uani 1 1 d . . . C14 C 0.0766(7) 0.6613(5) 0.7959(4) 0.0572(15) Uani 1 1 d . . . H14 H -0.0227 0.6155 0.8044 0.069 Uiso 1 1 calc R . . C15 C 0.0746(11) 0.6992(8) 0.6902(5) 0.096(3) Uani 1 1 d . . . H15A H -0.0351 0.6878 0.6571 0.115 Uiso 1 1 calc R . . H15B H 0.1030 0.7767 0.6867 0.115 Uiso 1 1 calc R . . C16 C 0.0774(16) 0.7543(8) 0.8679(7) 0.119(4) Uani 1 1 d . . . H16A H 0.0786 0.7256 0.9339 0.179 Uiso 1 1 calc R . . H16B H -0.0214 0.7984 0.8553 0.179 Uiso 1 1 calc R . . H16C H 0.1754 0.7988 0.8609 0.179 Uiso 1 1 calc R . . C17 C 0.5747(7) 0.5387(6) 0.9124(4) 0.064(2) Uani 1 1 d . . . C18 C 0.1150(7) 0.5108(7) 1.0174(4) 0.0544(12) Uani 1 1 d . . . C19 C 0.3680(7) 0.6484(6) 1.0293(5) 0.0605(17) Uani 1 1 d . . . C20 C 0.4280(9) 0.4328(7) 1.0634(5) 0.073(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 Mo1 0.04143(19) 0.0514(3) 0.03797(19) -0.0057(3) 0.00937(14) 0.0014(3) S1 0.0573(8) 0.0528(9) 0.0713(9) 0.0153(7) 0.0351(7) 0.0166(7) S2 0.0803(11) 0.0658(11) 0.0932(12) 0.0311(10) 0.0574(10) 0.0226(9) S3 0.0548(8) 0.0575(10) 0.0793(11) 0.0024(8) 0.0275(8) 0.0040(7) S4 0.0947(14) 0.0770(14) 0.1344(19) 0.0416(13) 0.0739(14) 0.0112(11) S5 0.0641(9) 0.0579(9) 0.0677(9) 0.0165(7) 0.0329(8) 0.0120(7) S6 0.0668(9) 0.0495(9) 0.0695(9) 0.0143(7) 0.0377(8) 0.0096(7) O1 0.066(2) 0.043(2) 0.051(2) -0.0031(18) 0.0199(18) -0.0083(18) O2 0.078(3) 0.078(3) 0.051(2) 0.005(2) 0.014(2) 0.039(3) O3 0.046(3) 0.178(8) 0.117(4) -0.028(4) 0.021(3) -0.025(3) O4 0.079(2) 0.085(3) 0.080(3) -0.004(4) 0.050(2) -0.001(4) O5 0.063(3) 0.090(4) 0.106(4) -0.056(3) 0.002(3) -0.004(3) O6 0.164(6) 0.166(7) 0.042(3) 0.027(3) 0.006(3) 0.078(5) N1 0.040(2) 0.040(2) 0.035(2) 0.0008(18) 0.0104(17) -0.0013(18) N2 0.039(2) 0.042(3) 0.044(2) 0.0005(19) 0.0103(17) 0.0045(18) C1 0.043(3) 0.041(3) 0.045(3) 0.004(2) 0.015(2) 0.003(2) C2 0.049(3) 0.057(3) 0.050(3) 0.004(2) 0.028(2) 0.001(2) C3 0.057(3) 0.055(3) 0.058(3) 0.000(3) 0.024(3) 0.006(3) C4 0.045(3) 0.055(4) 0.043(3) -0.005(3) 0.013(2) -0.005(3) C5A 0.065(11) 0.14(4) 0.13(2) 0.09(2) 0.069(12) 0.035(14) C5B 0.18(3) 0.057(14) 0.102(16) 0.026(11) 0.103(17) 0.059(16) C6A 0.069(9) 0.070(13) 0.074(11) 0.019(10) 0.031(7) -0.015(9) C6B 0.120(16) 0.107(19) 0.052(9) -0.009(10) 0.046(9) 0.020(14) C7 0.056(3) 0.052(3) 0.054(3) 0.001(4) 0.024(2) -0.003(4) C8 0.045(2) 0.045(3) 0.040(2) -0.007(3) 0.0161(17) -0.005(3) C9 0.042(3) 0.043(3) 0.035(2) 0.001(2) 0.007(2) -0.001(2) C10 0.044(3) 0.046(3) 0.046(3) 0.008(2) 0.015(2) -0.001(2) C11 0.059(3) 0.053(4) 0.061(3) 0.001(3) 0.018(3) -0.010(3) C12 0.049(3) 0.075(5) 0.070(4) -0.008(3) 0.017(3) -0.008(3) C13 0.045(3) 0.046(3) 0.038(2) -0.001(2) 0.009(2) 0.008(2) C14 0.048(3) 0.064(4) 0.060(3) -0.003(3) 0.010(3) 0.018(3) C15 0.114(6) 0.115(7) 0.058(4) -0.002(4) 0.007(4) 0.079(6) C16 0.171(10) 0.094(7) 0.089(6) -0.033(5) -0.017(6) 0.082(7) C17 0.056(3) 0.081(6) 0.053(3) -0.010(3) 0.001(2) -0.004(3) C18 0.071(3) 0.045(3) 0.049(2) -0.005(4) 0.016(2) -0.003(4) C19 0.040(3) 0.080(5) 0.063(4) -0.016(4) 0.012(3) -0.001(3) C20 0.077(5) 0.098(6) 0.046(4) -0.014(4) 0.017(3) 0.012(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 Mo1 C20 1.928(8) . ? Mo1 C19 1.938(7) . ? Mo1 C18 2.018(5) . ? Mo1 C17 2.034(6) . ? Mo1 N1 2.260(4) . ? Mo1 N2 2.277(4) . ? S1 C1 1.729(5) . ? S1 C2 1.744(6) . ? S2 C4 1.744(5) . ? S2 C3 1.752(6) . ? S3 C5B 1.65(3) . ? S3 C4 1.733(6) . ? S3 C5A 1.91(3) . ? S4 C6B 1.702(18) . ? S4 C7 1.724(6) . ? S4 C6A 1.739(18) . ? S5 C3 1.738(6) . ? S5 C7 1.742(5) . ? S6 C8 1.748(5) . ? S6 C2 1.749(6) . ? O1 C9 1.342(6) . ? O1 C11 1.463(6) . ? O2 C13 1.333(6) . ? O2 C15 1.466(7) . ? O3 C17 1.130(7) . ? O4 C18 1.152(6) . ? O5 C19 1.173(8) . ? O6 C20 1.182(9) . ? N1 C9 1.273(6) . ? N1 C10 1.482(6) . ? N2 C13 1.291(6) . ? N2 C14 1.479(7) . ? C1 C8 1.342(9) . ? C1 C9 1.465(7) . ? C2 C3 1.373(7) . ? C4 C7 1.356(9) . ? C5A C6B 1.32(4) . ? C5B C6A 1.59(4) . ? C8 C13 1.460(7) . ? C10 C12 1.499(8) . ? C10 C11 1.518(8) . ? C14 C16 1.494(10) . ? C14 C15 1.504(9) . ? 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 C20 Mo1 C19 88.6(3) . . ? C20 Mo1 C18 86.7(3) . . ? C19 Mo1 C18 82.9(3) . . ? C20 Mo1 C17 87.4(3) . . ? C19 Mo1 C17 85.8(3) . . ? C18 Mo1 C17 167.4(2) . . ? C20 Mo1 N1 93.2(3) . . ? C19 Mo1 N1 178.1(2) . . ? C18 Mo1 N1 96.5(2) . . ? C17 Mo1 N1 94.9(2) . . ? C20 Mo1 N2 172.3(3) . . ? C19 Mo1 N2 99.0(2) . . ? C18 Mo1 N2 95.6(2) . . ? C17 Mo1 N2 91.7(2) . . ? N1 Mo1 N2 79.16(15) . . ? C1 S1 C2 94.9(3) . . ? C4 S2 C3 94.7(3) . . ? C5B S3 C4 104.1(12) . . ? C5B S3 C5A 12(2) . . ? C4 S3 C5A 99.9(9) . . ? C6B S4 C7 100.2(8) . . ? C6B S4 C6A 30.4(8) . . ? C7 S4 C6A 105.3(6) . . ? C3 S5 C7 94.7(3) . . ? C8 S6 C2 94.8(3) . . ? C9 O1 C11 105.5(4) . . ? C13 O2 C15 105.3(4) . . ? C9 N1 C10 106.7(4) . . ? C9 N1 Mo1 127.4(3) . . ? C10 N1 Mo1 125.8(3) . . ? C13 N2 C14 106.2(4) . . ? C13 N2 Mo1 127.5(3) . . ? C14 N2 Mo1 126.2(3) . . ? C8 C1 C9 125.3(4) . . ? C8 C1 S1 118.3(4) . . ? C9 C1 S1 116.2(4) . . ? C3 C2 S1 121.9(5) . . ? C3 C2 S6 122.7(4) . . ? S1 C2 S6 115.2(3) . . ? C2 C3 S5 123.7(5) . . ? C2 C3 S2 121.2(5) . . ? S5 C3 S2 115.1(3) . . ? C7 C4 S3 128.0(4) . . ? C7 C4 S2 116.7(4) . . ? S3 C4 S2 115.2(3) . . ? C6B C5A S3 120.3(19) . . ? C6A C5B S3 117.6(17) . . ? C5B C6A S4 117.8(15) . . ? C5A C6B S4 119(2) . . ? C4 C7 S4 127.0(4) . . ? C4 C7 S5 117.5(4) . . ? S4 C7 S5 115.5(4) . . ? C1 C8 C13 127.2(5) . . ? C1 C8 S6 116.8(4) . . ? C13 C8 S6 115.9(5) . . ? N1 C9 O1 118.0(4) . . ? N1 C9 C1 127.5(5) . . ? O1 C9 C1 114.5(4) . . ? N1 C10 C12 109.3(5) . . ? N1 C10 C11 103.1(4) . . ? C12 C10 C11 112.6(5) . . ? O1 C11 C10 103.7(4) . . ? N2 C13 O2 118.4(4) . . ? N2 C13 C8 127.8(5) . . ? O2 C13 C8 113.8(4) . . ? N2 C14 C16 112.9(6) . . ? N2 C14 C15 104.1(4) . . ? C16 C14 C15 113.0(7) . . ? O2 C15 C14 104.7(5) . . ? O3 C17 Mo1 172.6(6) . . ? O4 C18 Mo1 170.0(5) . . ? O5 C19 Mo1 178.4(6) . . ? O6 C20 Mo1 178.2(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.595 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.078 #===END data_5a _database_code_depnum_ccdc_archive 'CCDC 718618' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ((S)-EDT-TTF-bis(Me-Ox))W(CO)4 _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 N2 O6 S6 W' _chemical_formula_sum 'C20 H16 N2 O6 S6 W' _chemical_formula_weight 756.56 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' W W -0.8490 6.8722 '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 monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9843(3) _cell_length_b 12.1519(16) _cell_length_c 13.4532(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.646(5) _cell_angle_gamma 90.00 _cell_volume 1302.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 238 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 4.954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.662416 _exptl_absorpt_correction_T_max 1 _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 14769 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5803 _reflns_number_gt 5335 _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^)+(0.0202P)^2^+1.1726P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration syn _refine_ls_abs_structure_Flack -0.020(5) _refine_ls_number_reflns 5803 _refine_ls_number_parameters 334 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0507 _refine_ls_wR_factor_gt 0.0472 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.063 _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 W1 W 0.336975(16) 0.51514(2) 0.953731(10) 0.03233(5) Uani 1 1 d . . . S1 S 0.63693(15) 0.35007(10) 0.67248(10) 0.0481(3) Uani 1 1 d . . . S2 S 0.96267(18) 0.35307(12) 0.54473(12) 0.0633(4) Uani 1 1 d . . . S3 S 1.29151(16) 0.34798(11) 0.45851(11) 0.0516(3) Uani 1 1 d . . . S4 S 1.1698(2) 0.59704(14) 0.35348(16) 0.0828(6) Uani 1 1 d . . . S5 S 0.86318(16) 0.56843(11) 0.46000(11) 0.0520(3) Uani 1 1 d . . . S6 S 0.55276(17) 0.57763(10) 0.60896(11) 0.0499(3) Uani 1 1 d . . . O1 O 0.3364(4) 0.2376(2) 0.7426(2) 0.0405(7) Uani 1 1 d . . . O2 O 0.1995(5) 0.6324(3) 0.6473(2) 0.0560(10) Uani 1 1 d . . . O3 O 0.7105(5) 0.5598(5) 0.9010(4) 0.099(2) Uani 1 1 d . . . O4 O 0.0046(4) 0.5157(6) 1.0666(2) 0.0695(9) Uani 1 1 d . . . O5 O 0.3867(5) 0.7273(4) 1.0814(4) 0.0750(13) Uani 1 1 d . . . O6 O 0.4913(8) 0.3780(5) 1.1312(3) 0.108(2) Uani 1 1 d . . . N1 N 0.2927(4) 0.3648(3) 0.8594(2) 0.0284(7) Uani 1 1 d . . . N2 N 0.2308(4) 0.5911(3) 0.8108(3) 0.0305(7) Uani 1 1 d . . . C1 C 0.4628(5) 0.4112(3) 0.7204(3) 0.0317(9) Uani 1 1 d . . . C2 C 0.6903(6) 0.4653(4) 0.6025(3) 0.0387(10) Uani 1 1 d . . . C3 C 0.8225(6) 0.4647(4) 0.5456(4) 0.0402(10) Uani 1 1 d . . . C4 C 1.1059(5) 0.4207(4) 0.4730(3) 0.0365(10) Uani 1 1 d . . . C5A C 1.396(2) 0.4339(15) 0.3656(14) 0.053(4) Uani 0.50 1 d P . . H5A1 H 1.4697 0.4860 0.4010 0.064 Uiso 0.50 1 calc PR . . H5A2 H 1.4644 0.3866 0.3269 0.064 Uiso 0.50 1 calc PR . . C5B C 1.350(2) 0.3957(13) 0.3448(15) 0.062(5) Uani 0.50 1 d P . . H5B1 H 1.4600 0.3665 0.3328 0.074 Uiso 0.50 1 calc PR . . H5B2 H 1.2714 0.3680 0.2928 0.074 Uiso 0.50 1 calc PR . . C6A C 1.3560(16) 0.5245(17) 0.3378(12) 0.068(4) Uani 0.50 1 d P . . H6A1 H 1.3945 0.5437 0.2731 0.081 Uiso 0.50 1 calc PR . . H6A2 H 1.4400 0.5506 0.3875 0.081 Uiso 0.50 1 calc PR . . C6B C 1.2765(17) 0.4963(17) 0.2957(8) 0.067(5) Uani 0.50 1 d P . . H6B1 H 1.1964 0.4452 0.2640 0.081 Uiso 0.50 1 calc PR . . H6B2 H 1.3391 0.5294 0.2439 0.081 Uiso 0.50 1 calc PR . . C7 C 1.0595(4) 0.5153(6) 0.4330(3) 0.0422(8) Uani 1 1 d . . . C8 C 0.4249(4) 0.5139(6) 0.6933(2) 0.0334(7) Uani 1 1 d . . . C9 C 0.3600(5) 0.3399(3) 0.7799(3) 0.0298(8) Uani 1 1 d . . . C10 C 0.1850(6) 0.2693(4) 0.8840(4) 0.0383(11) Uani 1 1 d . . . H10 H 0.2022 0.2492 0.9545 0.046 Uiso 1 1 calc R . . C11 C 0.2453(6) 0.1791(4) 0.8176(4) 0.0458(11) Uani 1 1 d . . . H11A H 0.3187 0.1284 0.8551 0.055 Uiso 1 1 calc R . . H11B H 0.1513 0.1384 0.7866 0.055 Uiso 1 1 calc R . . C12 C 0.0034(6) 0.2993(6) 0.8576(5) 0.0519(16) Uani 1 1 d . . . H12A H -0.0298 0.3574 0.9005 0.078 Uiso 1 1 calc R . . H12B H -0.0663 0.2360 0.8661 0.078 Uiso 1 1 calc R . . H12C H -0.0087 0.3233 0.7896 0.078 Uiso 1 1 calc R . . C13 C 0.2808(5) 0.5794(3) 0.7227(3) 0.0334(9) Uani 1 1 d . . . C14 C 0.0764(6) 0.6605(4) 0.7994(4) 0.0465(12) Uani 1 1 d . . . H14 H -0.0215 0.6134 0.8071 0.056 Uiso 1 1 calc R . . C15 C 0.0744(9) 0.6981(7) 0.6931(5) 0.085(2) Uani 1 1 d . . . H15A H -0.0355 0.6866 0.6598 0.103 Uiso 1 1 calc R . . H15B H 0.1020 0.7757 0.6898 0.103 Uiso 1 1 calc R . . C16 C 0.0736(13) 0.7515(7) 0.8728(6) 0.096(3) Uani 1 1 d . . . H16A H 0.0757 0.7215 0.9389 0.144 Uiso 1 1 calc R . . H16B H -0.0268 0.7941 0.8602 0.144 Uiso 1 1 calc R . . H16C H 0.1699 0.7977 0.8667 0.144 Uiso 1 1 calc R . . C17 C 0.5750(5) 0.5390(6) 0.9138(4) 0.0529(19) Uani 1 1 d . . . C18 C 0.1176(5) 0.5099(7) 1.0193(3) 0.0413(9) Uani 1 1 d . . . C19 C 0.3697(6) 0.6492(5) 1.0329(4) 0.0492(13) Uani 1 1 d . . . C20 C 0.4340(8) 0.4299(6) 1.0663(4) 0.0608(16) 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 W1 0.02953(7) 0.04071(8) 0.02724(7) -0.00518(12) 0.00570(5) 0.00173(11) S1 0.0457(6) 0.0412(6) 0.0612(8) 0.0148(6) 0.0323(6) 0.0161(5) S2 0.0666(8) 0.0502(8) 0.0792(10) 0.0271(7) 0.0509(8) 0.0195(6) S3 0.0421(6) 0.0454(7) 0.0697(9) 0.0027(6) 0.0234(6) 0.0059(5) S4 0.0812(11) 0.0582(9) 0.1166(15) 0.0342(10) 0.0659(11) 0.0068(8) S5 0.0531(7) 0.0459(7) 0.0607(8) 0.0176(6) 0.0317(6) 0.0124(5) S6 0.0559(7) 0.0379(6) 0.0600(8) 0.0142(6) 0.0345(6) 0.0105(5) O1 0.0494(18) 0.0344(16) 0.0389(18) -0.0057(14) 0.0134(14) -0.0049(14) O2 0.069(2) 0.066(2) 0.0338(18) 0.0061(17) 0.0085(16) 0.0350(19) O3 0.0324(19) 0.166(6) 0.099(3) -0.027(3) 0.011(2) -0.020(2) O4 0.0695(19) 0.077(2) 0.068(2) 0.006(4) 0.0454(17) 0.005(4) O5 0.048(2) 0.083(3) 0.093(3) -0.056(3) 0.004(2) -0.008(2) O6 0.136(5) 0.148(5) 0.040(2) 0.020(3) 0.003(3) 0.070(4) N1 0.0275(16) 0.0322(18) 0.0263(17) -0.0013(14) 0.0074(13) -0.0006(14) N2 0.0271(16) 0.0316(18) 0.0338(19) -0.0029(15) 0.0087(14) 0.0028(14) C1 0.0288(19) 0.034(2) 0.034(2) 0.0006(18) 0.0123(17) 0.0024(16) C2 0.040(2) 0.038(2) 0.039(3) 0.0024(19) 0.0179(19) 0.0011(18) C3 0.043(2) 0.036(2) 0.044(3) 0.002(2) 0.020(2) 0.0055(19) C4 0.038(2) 0.037(2) 0.036(2) -0.0064(19) 0.0178(18) -0.0028(18) C5A 0.043(7) 0.053(11) 0.066(9) -0.001(8) 0.026(6) -0.014(7) C5B 0.070(12) 0.042(9) 0.081(12) -0.011(7) 0.057(10) -0.005(7) C6A 0.062(7) 0.058(11) 0.088(10) 0.003(10) 0.040(6) -0.022(9) C6B 0.072(8) 0.095(15) 0.038(6) -0.012(8) 0.022(5) 0.010(9) C7 0.0433(19) 0.0388(19) 0.047(2) 0.006(4) 0.0221(16) -0.005(4) C8 0.0341(16) 0.0352(17) 0.0322(17) 0.002(3) 0.0119(13) 0.002(3) C9 0.0274(19) 0.029(2) 0.033(2) 0.0034(17) 0.0042(16) 0.0030(16) C10 0.037(2) 0.041(3) 0.038(3) 0.007(2) 0.010(2) -0.005(2) C11 0.045(3) 0.042(3) 0.051(3) 0.002(2) 0.012(2) -0.009(2) C12 0.036(3) 0.070(4) 0.051(3) -0.010(3) 0.013(2) -0.011(2) C13 0.033(2) 0.034(2) 0.033(2) 0.0011(18) 0.0030(17) 0.0059(17) C14 0.037(2) 0.050(3) 0.054(3) 0.001(2) 0.008(2) 0.016(2) C15 0.091(5) 0.112(6) 0.053(4) -0.002(4) 0.002(3) 0.075(4) C16 0.135(8) 0.076(5) 0.074(5) -0.026(4) -0.021(5) 0.067(6) C17 0.032(2) 0.080(6) 0.047(3) -0.013(3) 0.0060(18) -0.005(2) C18 0.047(2) 0.040(2) 0.0386(19) -0.003(4) 0.0163(16) -0.004(4) C19 0.034(2) 0.065(4) 0.049(3) -0.021(3) 0.004(2) 0.000(2) C20 0.075(4) 0.075(4) 0.033(3) -0.002(3) 0.005(3) 0.027(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 W1 C20 1.954(6) . ? W1 C19 1.955(5) . ? W1 C18 2.012(4) . ? W1 C17 2.028(4) . ? W1 N1 2.239(3) . ? W1 N2 2.250(4) . ? S1 C1 1.736(4) . ? S1 C2 1.755(5) . ? S2 C4 1.748(4) . ? S2 C3 1.760(5) . ? S3 C5B 1.728(18) . ? S3 C4 1.747(4) . ? S3 C5A 1.864(17) . ? S4 C6B 1.707(15) . ? S4 C7 1.740(5) . ? S4 C6A 1.753(16) . ? S5 C3 1.752(5) . ? S5 C7 1.755(5) . ? S6 C8 1.754(5) . ? S6 C2 1.757(5) . ? O1 C9 1.349(5) . ? O1 C11 1.464(5) . ? O2 C13 1.335(5) . ? O2 C15 1.447(6) . ? O3 C17 1.135(6) . ? O4 C18 1.138(4) . ? O5 C19 1.155(6) . ? O6 C20 1.148(7) . ? N1 C9 1.265(5) . ? N1 C10 1.494(5) . ? N2 C13 1.282(5) . ? N2 C14 1.493(5) . ? C1 C8 1.330(8) . ? C1 C9 1.465(5) . ? C2 C3 1.342(6) . ? C4 C7 1.313(8) . ? C5A C6B 1.50(2) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C5B C6A 1.57(2) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C8 C13 1.474(6) . ? C10 C11 1.513(7) . ? C10 C12 1.515(7) . ? C10 H10 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 C16 1.483(9) . ? C14 C15 1.500(8) . ? C14 H14 0.9800 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 W1 C19 89.3(3) . . ? C20 W1 C18 87.5(3) . . ? C19 W1 C18 82.9(3) . . ? C20 W1 C17 87.1(3) . . ? C19 W1 C17 86.0(2) . . ? C18 W1 C17 167.7(2) . . ? C20 W1 N1 92.7(2) . . ? C19 W1 N1 177.9(2) . . ? C18 W1 N1 96.5(2) . . ? C17 W1 N1 94.77(19) . . ? C20 W1 N2 171.6(2) . . ? C19 W1 N2 98.8(2) . . ? C18 W1 N2 95.53(17) . . ? C17 W1 N2 91.37(18) . . ? N1 W1 N2 79.24(13) . . ? C1 S1 C2 94.9(2) . . ? C4 S2 C3 94.6(2) . . ? C5B S3 C4 102.0(7) . . ? C5B S3 C5A 20.2(6) . . ? C4 S3 C5A 102.1(6) . . ? C6B S4 C7 99.1(6) . . ? C6B S4 C6A 29.8(6) . . ? C7 S4 C6A 104.7(6) . . ? C3 S5 C7 94.4(3) . . ? C8 S6 C2 94.6(3) . . ? C9 O1 C11 104.8(3) . . ? C13 O2 C15 104.9(4) . . ? C9 N1 C10 106.4(3) . . ? C9 N1 W1 127.9(3) . . ? C10 N1 W1 125.5(3) . . ? C13 N2 C14 105.8(4) . . ? C13 N2 W1 128.4(3) . . ? C14 N2 W1 125.7(3) . . ? C8 C1 C9 125.4(3) . . ? C8 C1 S1 118.2(3) . . ? C9 C1 S1 116.1(3) . . ? C3 C2 S1 121.9(4) . . ? C3 C2 S6 123.3(4) . . ? S1 C2 S6 114.8(2) . . ? C2 C3 S5 123.8(4) . . ? C2 C3 S2 122.1(4) . . ? S5 C3 S2 113.9(2) . . ? C7 C4 S3 128.1(3) . . ? C7 C4 S2 117.4(3) . . ? S3 C4 S2 114.4(3) . . ? C6B C5A S3 114.3(11) . . ? C6B C5A H5A1 108.7 . . ? S3 C5A H5A1 108.7 . . ? C6B C5A H5A2 108.7 . . ? S3 C5A H5A2 108.7 . . ? H5A1 C5A H5A2 107.6 . . ? C6A C5B S3 113.5(11) . . ? C6A C5B H5B1 108.9 . . ? S3 C5B H5B1 108.9 . . ? C6A C5B H5B2 108.9 . . ? S3 C5B H5B2 108.9 . . ? H5B1 C5B H5B2 107.7 . . ? C5B C6A S4 117.7(10) . . ? C5B C6A H6A1 107.9 . . ? S4 C6A H6A1 107.9 . . ? C5B C6A H6A2 107.9 . . ? S4 C6A H6A2 107.9 . . ? H6A1 C6A H6A2 107.2 . . ? C5A C6B S4 113.1(10) . . ? C5A C6B H6B1 109.0 . . ? S4 C6B H6B1 109.0 . . ? C5A C6B H6B2 109.0 . . ? S4 C6B H6B2 109.0 . . ? H6B1 C6B H6B2 107.8 . . ? C4 C7 S4 127.7(3) . . ? C4 C7 S5 118.0(3) . . ? S4 C7 S5 114.2(4) . . ? C1 C8 C13 127.0(4) . . ? C1 C8 S6 117.4(3) . . ? C13 C8 S6 115.6(5) . . ? N1 C9 O1 118.6(4) . . ? N1 C9 C1 127.1(4) . . ? O1 C9 C1 114.3(3) . . ? N1 C10 C11 102.9(3) . . ? N1 C10 C12 108.5(4) . . ? C11 C10 C12 111.8(4) . . ? N1 C10 H10 111.1 . . ? C11 C10 H10 111.1 . . ? C12 C10 H10 111.1 . . ? O1 C11 C10 104.3(4) . . ? O1 C11 H11A 110.9 . . ? C10 C11 H11A 110.9 . . ? O1 C11 H11B 110.9 . . ? C10 C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 O2 118.9(4) . . ? N2 C13 C8 127.1(4) . . ? O2 C13 C8 114.0(4) . . ? C16 C14 N2 113.6(5) . . ? C16 C14 C15 114.0(6) . . ? N2 C14 C15 103.2(4) . . ? C16 C14 H14 108.6 . . ? N2 C14 H14 108.6 . . ? C15 C14 H14 108.6 . . ? O2 C15 C14 105.8(4) . . ? O2 C15 H15A 110.6 . . ? C14 C15 H15A 110.6 . . ? O2 C15 H15B 110.6 . . ? C14 C15 H15B 110.6 . . ? H15A C15 H15B 108.7 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C17 W1 172.1(5) . . ? O4 C18 W1 170.4(5) . . ? O5 C19 W1 178.3(5) . . ? O6 C20 W1 178.6(6) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.625 _refine_diff_density_min -0.810 _refine_diff_density_rms 0.083