data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email maria.babashkina@ksu.ru _publ_contact_author_name 'Maria Babashkina' _publ_author_name 'Maria Babashkina' data_saf64 _database_code_depnum_ccdc_archive 'CCDC 844829' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H36 N4 O4 P2 S4' _chemical_formula_sum 'C20 H36 N4 O4 P2 S4' _chemical_formula_weight 586.71 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' P P 0.1023 0.0942 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.695(9) _cell_length_b 8.371(3) _cell_length_c 15.078(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.54(4) _cell_angle_gamma 90.00 _cell_volume 2957.6(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1281 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 36.55 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.461 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8996 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2009)' _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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12383 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3387 _reflns_number_gt 2437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0456P)^2^+0.2095P] 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 3387 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0860 _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 S1 S 0.84043(2) 0.59954(7) 1.07043(4) 0.02834(15) Uani 1 1 d . . . S2 S 1.03659(2) 0.65666(7) 0.91577(4) 0.02859(15) Uani 1 1 d . . . P1 P 0.87230(2) 0.73278(7) 0.98730(4) 0.02103(14) Uani 1 1 d . . . O1 O 0.84191(6) 0.72664(16) 0.88707(9) 0.0233(3) Uani 1 1 d . . . O2 O 0.87524(6) 0.91882(17) 1.00340(10) 0.0259(3) Uani 1 1 d . . . N1 N 0.94146(7) 0.6939(2) 0.98575(11) 0.0214(4) Uani 1 1 d . . . H1A H 0.9573 0.6252 1.0261 0.026 Uiso 1 1 d R . . N2 N 0.96090(7) 0.8966(2) 0.89151(11) 0.0219(4) Uani 1 1 d . . . H2A H 0.9335 0.9464 0.9139 0.026 Uiso 1 1 d R . . C1 C 0.97705(8) 0.7558(3) 0.92942(14) 0.0213(4) Uani 1 1 d . . . C2 C 0.98222(8) 0.9774(2) 0.82002(13) 0.0191(4) Uani 1 1 d . . . C3 C 1.0000 0.8929(3) 0.7500 0.0205(6) Uani 1 2 d S . . H3B H 1.0000 0.7794 0.7500 0.025 Uiso 1 2 calc SR . . C5 C 0.98144(9) 1.1428(2) 0.82044(15) 0.0254(5) Uani 1 1 d . . . H5A H 0.9684 1.1991 0.8682 0.030 Uiso 1 1 calc R . . C6 C 1.0000 1.2255(4) 0.7500 0.0292(7) Uani 1 2 d S . . H6A H 1.0000 1.3389 0.7500 0.035 Uiso 1 2 calc SR . . C8 C 0.82326(10) 0.5739(3) 0.84347(15) 0.0292(5) Uani 1 1 d . . . H8A H 0.8063 0.5051 0.8869 0.035 Uiso 1 1 calc R . . C9 C 0.77768(11) 0.6168(3) 0.76644(17) 0.0396(6) Uani 1 1 d . . . H9A H 0.7477 0.6789 0.7889 0.059 Uiso 1 1 calc R . . H9B H 0.7612 0.5189 0.7379 0.059 Uiso 1 1 calc R . . H9C H 0.7945 0.6804 0.7225 0.059 Uiso 1 1 calc R . . C10 C 0.87376(12) 0.4891(3) 0.81456(18) 0.0476(7) Uani 1 1 d . . . H10A H 0.8608 0.3911 0.7823 0.071 Uiso 1 1 calc R . . H10B H 0.9013 0.4621 0.8675 0.071 Uiso 1 1 calc R . . H10C H 0.8920 0.5592 0.7751 0.071 Uiso 1 1 calc R . . C11 C 0.82449(10) 1.0111(3) 1.0159(2) 0.0468(8) Uani 1 1 d . . . H11A H 0.7896 0.9432 1.0019 0.056 Uiso 1 1 calc R . . C12 C 0.83205(14) 1.0615(4) 1.1115(2) 0.0768(12) Uani 1 1 d . . . H12A H 0.8394 0.9674 1.1501 0.115 Uiso 1 1 calc R . . H12B H 0.7973 1.1151 1.1240 0.115 Uiso 1 1 calc R . . H12C H 0.8644 1.1353 1.1233 0.115 Uiso 1 1 calc R . . C13 C 0.82231(13) 1.1477(3) 0.9492(3) 0.0769(12) Uani 1 1 d . . . H13A H 0.8215 1.1045 0.8886 0.115 Uiso 1 1 calc R . . H13B H 0.8562 1.2152 0.9644 0.115 Uiso 1 1 calc R . . H13C H 0.7879 1.2115 0.9516 0.115 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0271(3) 0.0343(3) 0.0260(3) 0.0056(2) 0.0118(2) 0.0015(2) S2 0.0205(3) 0.0312(3) 0.0363(3) 0.0133(3) 0.0116(2) 0.0070(2) P1 0.0210(3) 0.0217(3) 0.0217(3) 0.0006(2) 0.0076(2) 0.0022(2) O1 0.0255(8) 0.0206(8) 0.0239(8) 0.0029(6) 0.0042(6) 0.0011(6) O2 0.0223(8) 0.0237(8) 0.0335(9) -0.0042(6) 0.0102(7) 0.0029(6) N1 0.0202(9) 0.0250(10) 0.0198(9) 0.0052(7) 0.0063(7) 0.0040(7) N2 0.0243(9) 0.0211(9) 0.0225(9) 0.0016(7) 0.0106(7) 0.0052(7) C1 0.0210(10) 0.0232(11) 0.0202(11) -0.0002(9) 0.0046(9) 0.0009(8) C2 0.0171(10) 0.0194(11) 0.0210(11) 0.0036(8) 0.0034(8) 0.0008(8) C3 0.0212(15) 0.0152(14) 0.0256(16) 0.000 0.0051(12) 0.000 C5 0.0286(12) 0.0239(12) 0.0249(12) -0.0047(9) 0.0081(9) 0.0032(9) C6 0.0420(19) 0.0129(15) 0.0345(19) 0.000 0.0115(15) 0.000 C8 0.0388(13) 0.0234(12) 0.0249(12) 0.0001(9) 0.0027(10) -0.0042(10) C9 0.0413(15) 0.0409(15) 0.0337(14) 0.0067(11) -0.0046(12) -0.0105(12) C10 0.0529(17) 0.0447(17) 0.0431(17) -0.0196(13) 0.0000(13) 0.0085(13) C11 0.0160(12) 0.0324(15) 0.093(2) -0.0221(14) 0.0115(13) 0.0025(10) C12 0.067(2) 0.072(2) 0.107(3) -0.059(2) 0.063(2) -0.0342(18) C13 0.0469(19) 0.0359(17) 0.137(4) 0.005(2) -0.024(2) 0.0105(14) _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 P1 1.9148(9) . ? S2 C1 1.676(2) . ? P1 O1 1.5754(17) . ? P1 O2 1.5760(16) . ? P1 N1 1.6745(18) . ? O1 C8 1.475(3) . ? O2 C11 1.465(3) . ? N1 C1 1.383(3) . ? N1 H1A 0.8801 . ? N2 C1 1.340(3) . ? N2 C2 1.427(2) . ? N2 H2A 0.8801 . ? C2 C5 1.384(3) . ? C2 C3 1.387(2) . ? C3 C2 1.387(2) 2_756 ? C3 H3B 0.9500 . ? C5 C6 1.393(3) . ? C5 H5A 0.9500 . ? C6 C5 1.393(3) 2_756 ? C6 H6A 0.9500 . ? C8 C9 1.507(3) . ? C8 C10 1.510(3) . ? C8 H8A 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.487(4) . ? C11 C13 1.518(4) . ? C11 H11A 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 O1 P1 O2 100.57(8) . . ? O1 P1 N1 106.80(9) . . ? O2 P1 N1 99.97(8) . . ? O1 P1 S1 116.13(7) . . ? O2 P1 S1 119.18(6) . . ? N1 P1 S1 112.20(7) . . ? C8 O1 P1 121.33(13) . . ? C11 O2 P1 121.50(14) . . ? C1 N1 P1 128.53(15) . . ? C1 N1 H1A 115.7 . . ? P1 N1 H1A 115.8 . . ? C1 N2 C2 128.93(17) . . ? C1 N2 H2A 115.7 . . ? C2 N2 H2A 115.4 . . ? N2 C1 N1 115.45(17) . . ? N2 C1 S2 125.11(16) . . ? N1 C1 S2 119.41(16) . . ? C5 C2 C3 121.3(2) . . ? C5 C2 N2 117.67(18) . . ? C3 C2 N2 120.95(19) . . ? C2 C3 C2 118.7(3) 2_756 . ? C2 C3 H3B 120.7 2_756 . ? C2 C3 H3B 120.7 . . ? C2 C5 C6 119.2(2) . . ? C2 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C5 C6 C5 120.4(3) 2_756 . ? C5 C6 H6A 119.8 2_756 . ? C5 C6 H6A 119.8 . . ? O1 C8 C9 105.68(18) . . ? O1 C8 C10 109.77(19) . . ? C9 C8 C10 113.4(2) . . ? O1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C10 C8 H8A 109.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C12 106.9(2) . . ? O2 C11 C13 105.1(2) . . ? C12 C11 C13 114.5(3) . . ? O2 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? C13 C11 H11A 110.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C8 -172.82(14) . . . . ? N1 P1 O1 C8 83.27(16) . . . . ? S1 P1 O1 C8 -42.73(16) . . . . ? O1 P1 O2 C11 74.60(19) . . . . ? N1 P1 O2 C11 -176.04(18) . . . . ? S1 P1 O2 C11 -53.5(2) . . . . ? O1 P1 N1 C1 45.6(2) . . . . ? O2 P1 N1 C1 -58.69(19) . . . . ? S1 P1 N1 C1 173.98(16) . . . . ? C2 N2 C1 N1 -168.27(19) . . . . ? C2 N2 C1 S2 13.7(3) . . . . ? P1 N1 C1 N2 23.0(3) . . . . ? P1 N1 C1 S2 -158.90(12) . . . . ? C1 N2 C2 C5 -148.7(2) . . . . ? C1 N2 C2 C3 35.0(3) . . . . ? C5 C2 C3 C2 0.67(14) . . . 2_756 ? N2 C2 C3 C2 176.9(2) . . . 2_756 ? C3 C2 C5 C6 -1.3(3) . . . . ? N2 C2 C5 C6 -177.70(16) . . . . ? C2 C5 C6 C5 0.65(14) . . . 2_756 ? P1 O1 C8 C9 158.29(15) . . . . ? P1 O1 C8 C10 -79.1(2) . . . . ? P1 O2 C11 C12 109.6(2) . . . . ? P1 O2 C11 C13 -128.29(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A S2 0.88 2.51 3.295(2) 148.4 5_767 N2 H2A O2 0.88 2.08 2.832(2) 142.6 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.356 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.063 # Attachment '- 4.cif' data_saf65 _database_code_depnum_ccdc_archive 'CCDC 844830' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H36 N4 O4 P2 S4' _chemical_formula_sum 'C20 H36 N4 O4 P2 S4' _chemical_formula_weight 586.71 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' P P 0.1023 0.0942 '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 7.697(2) _cell_length_b 8.166(2) _cell_length_c 12.500(4) _cell_angle_alpha 73.39(2) _cell_angle_beta 79.86(2) _cell_angle_gamma 80.27(2) _cell_volume 735.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2018 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 36.85 _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 0.464 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2009)' _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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10241 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3210 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0381P)^2^+0.2681P] 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 3210 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 S1 S 1.14288(4) 0.23793(4) 0.31540(3) 0.02218(9) Uani 1 1 d . . . S2 S 0.81296(5) 0.40636(4) -0.06567(3) 0.02211(10) Uani 1 1 d . . . P1 P 0.97704(4) 0.15293(4) 0.25344(3) 0.01548(9) Uani 1 1 d . . . O1 O 0.78028(12) 0.15661(11) 0.31704(8) 0.01830(19) Uani 1 1 d . . . O2 O 1.01416(12) -0.03958(11) 0.24592(7) 0.01874(19) Uani 1 1 d . . . N1 N 0.96450(14) 0.25768(14) 0.11828(9) 0.0171(2) Uani 1 1 d . . . H1A H 1.0431 0.3299 0.0867 0.021 Uiso 1 1 d R . . N2 N 0.77284(15) 0.09853(14) 0.08162(9) 0.0190(2) Uani 1 1 d . . . H2A H 0.8153 0.0186 0.1379 0.023 Uiso 1 1 d R . . C1 C 0.84747(17) 0.24593(16) 0.04952(10) 0.0167(2) Uani 1 1 d . . . C2 C 0.63469(17) 0.05468(16) 0.03688(10) 0.0166(2) Uani 1 1 d . . . C3 C 0.48719(18) 0.17075(17) 0.00471(11) 0.0196(3) Uani 1 1 d . . . H3B H 0.4778 0.2866 0.0083 0.024 Uiso 1 1 calc R . . C4 C 0.35350(17) 0.11542(16) -0.03271(11) 0.0188(3) Uani 1 1 d . . . H4B H 0.2529 0.1945 -0.0557 0.023 Uiso 1 1 calc R . . C8 C 0.69022(18) 0.30586(18) 0.35724(12) 0.0224(3) Uani 1 1 d . . . H8A H 0.7766 0.3512 0.3891 0.027 Uiso 1 1 calc R . . C9 C 0.5459(2) 0.2377(2) 0.44981(13) 0.0292(3) Uani 1 1 d . . . H9A H 0.5990 0.1447 0.5083 0.044 Uiso 1 1 calc R . . H9B H 0.4610 0.1933 0.4187 0.044 Uiso 1 1 calc R . . H9C H 0.4840 0.3308 0.4826 0.044 Uiso 1 1 calc R . . C10 C 0.6203(2) 0.4455(2) 0.26044(14) 0.0350(4) Uani 1 1 d . . . H10A H 0.7199 0.4827 0.2026 0.052 Uiso 1 1 calc R . . H10B H 0.5583 0.5437 0.2880 0.052 Uiso 1 1 calc R . . H10C H 0.5375 0.4005 0.2280 0.052 Uiso 1 1 calc R . . C11 C 1.03193(19) -0.18237(17) 0.34885(11) 0.0227(3) Uani 1 1 d . . . H11A H 1.0149 -0.1355 0.4162 0.027 Uiso 1 1 calc R . . C12 C 1.2170(2) -0.2745(2) 0.33367(13) 0.0315(3) Uani 1 1 d . . . H12A H 1.3036 -0.1941 0.3231 0.047 Uiso 1 1 calc R . . H12B H 1.2329 -0.3195 0.2674 0.047 Uiso 1 1 calc R . . H12C H 1.2353 -0.3701 0.4006 0.047 Uiso 1 1 calc R . . C13 C 0.8882(2) -0.2923(2) 0.35896(15) 0.0372(4) Uani 1 1 d . . . H13A H 0.8917 -0.3865 0.4281 0.056 Uiso 1 1 calc R . . H13B H 0.9074 -0.3402 0.2937 0.056 Uiso 1 1 calc R . . H13C H 0.7719 -0.2219 0.3617 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02157(17) 0.02604(18) 0.02230(17) -0.00479(13) -0.00983(13) -0.00782(13) S2 0.02970(19) 0.02145(17) 0.01718(16) 0.00215(12) -0.01044(13) -0.01372(13) P1 0.01611(16) 0.01540(16) 0.01586(16) -0.00228(12) -0.00540(12) -0.00434(12) O1 0.0178(4) 0.0174(4) 0.0203(4) -0.0045(3) -0.0028(3) -0.0047(3) O2 0.0234(5) 0.0153(4) 0.0171(4) -0.0019(3) -0.0056(4) -0.0025(4) N1 0.0188(5) 0.0173(5) 0.0163(5) -0.0005(4) -0.0054(4) -0.0088(4) N2 0.0222(6) 0.0162(5) 0.0202(5) -0.0002(4) -0.0100(4) -0.0075(4) C1 0.0181(6) 0.0174(6) 0.0165(6) -0.0045(5) -0.0033(5) -0.0058(5) C2 0.0187(6) 0.0182(6) 0.0150(5) -0.0029(5) -0.0035(5) -0.0089(5) C3 0.0223(6) 0.0152(6) 0.0236(6) -0.0055(5) -0.0052(5) -0.0056(5) C4 0.0191(6) 0.0159(6) 0.0218(6) -0.0029(5) -0.0055(5) -0.0040(5) C8 0.0204(6) 0.0217(6) 0.0265(7) -0.0093(5) -0.0019(5) -0.0023(5) C9 0.0236(7) 0.0387(8) 0.0274(7) -0.0123(6) 0.0001(6) -0.0073(6) C10 0.0345(8) 0.0271(8) 0.0355(8) -0.0039(6) -0.0022(7) 0.0076(6) C11 0.0324(7) 0.0167(6) 0.0161(6) -0.0005(5) -0.0051(5) 0.0001(5) C12 0.0353(8) 0.0311(8) 0.0291(8) -0.0101(6) -0.0159(6) 0.0087(6) C13 0.0400(9) 0.0248(8) 0.0404(9) 0.0025(7) 0.0000(7) -0.0114(7) _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 P1 1.9147(6) . ? S2 C1 1.6729(14) . ? P1 O2 1.5764(10) . ? P1 O1 1.5814(10) . ? P1 N1 1.6729(12) . ? O1 C8 1.4698(16) . ? O2 C11 1.4779(15) . ? N1 C1 1.3815(16) . ? N1 H1A 0.8793 . ? N2 C1 1.3477(16) . ? N2 C2 1.4228(16) . ? N2 H2A 0.8800 . ? C2 C3 1.3886(19) . ? C2 C4 1.3919(18) 2_655 ? C3 C4 1.3890(18) . ? C3 H3B 0.9500 . ? C4 C2 1.3919(18) 2_655 ? C4 H4B 0.9500 . ? C8 C9 1.507(2) . ? C8 C10 1.512(2) . ? C8 H8A 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.502(2) . ? C11 C13 1.506(2) . ? C11 H11A 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 O2 P1 O1 100.26(5) . . ? O2 P1 N1 100.79(6) . . ? O1 P1 N1 107.01(6) . . ? O2 P1 S1 118.79(4) . . ? O1 P1 S1 116.08(4) . . ? N1 P1 S1 112.07(5) . . ? C8 O1 P1 121.68(8) . . ? C11 O2 P1 120.26(8) . . ? C1 N1 P1 128.77(9) . . ? C1 N1 H1A 115.6 . . ? P1 N1 H1A 115.6 . . ? C1 N2 C2 128.79(11) . . ? C1 N2 H2A 115.6 . . ? C2 N2 H2A 115.6 . . ? N2 C1 N1 115.06(11) . . ? N2 C1 S2 125.30(10) . . ? N1 C1 S2 119.62(9) . . ? C3 C2 C4 120.06(12) . 2_655 ? C3 C2 N2 122.71(11) . . ? C4 C2 N2 117.11(12) 2_655 . ? C2 C3 C4 119.22(12) . . ? C2 C3 H3B 120.4 . . ? C4 C3 H3B 120.4 . . ? C3 C4 C2 120.72(12) . 2_655 ? C3 C4 H4B 119.6 . . ? C2 C4 H4B 119.6 2_655 . ? O1 C8 C9 105.54(11) . . ? O1 C8 C10 109.79(11) . . ? C9 C8 C10 113.38(13) . . ? O1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C10 C8 H8A 109.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C12 106.61(11) . . ? O2 C11 C13 106.59(12) . . ? C12 C11 C13 113.71(13) . . ? O2 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? C13 C11 H11A 109.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C8 172.45(9) . . . . ? N1 P1 O1 C8 -82.82(10) . . . . ? S1 P1 O1 C8 43.14(10) . . . . ? O1 P1 O2 C11 -69.00(10) . . . . ? N1 P1 O2 C11 -178.71(9) . . . . ? S1 P1 O2 C11 58.53(10) . . . . ? O2 P1 N1 C1 60.37(12) . . . . ? O1 P1 N1 C1 -43.99(13) . . . . ? S1 P1 N1 C1 -172.31(10) . . . . ? C2 N2 C1 N1 172.55(12) . . . . ? C2 N2 C1 S2 -9.2(2) . . . . ? P1 N1 C1 N2 -22.61(17) . . . . ? P1 N1 C1 S2 159.06(8) . . . . ? C1 N2 C2 C3 -40.2(2) . . . . ? C1 N2 C2 C4 143.78(14) . . . 2_655 ? C4 C2 C3 C4 -0.7(2) 2_655 . . . ? N2 C2 C3 C4 -176.65(12) . . . . ? C2 C3 C4 C2 0.8(2) . . . 2_655 ? P1 O1 C8 C9 -157.60(9) . . . . ? P1 O1 C8 C10 79.86(13) . . . . ? P1 O2 C11 C12 -118.15(11) . . . . ? P1 O2 C11 C13 120.07(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A S2 0.88 2.51 3.3246(14) 153.8 2_765 N2 H2A O2 0.88 2.12 2.8724(16) 142.7 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.416 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.059 # Attachment '- 5.cif' data_saf68 _database_code_depnum_ccdc_archive 'CCDC 844831' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H42 N4 O4 P2 S4, 0.5(C6 H14)' _chemical_formula_sum 'C30 H49 N4 O4 P2 S4' _chemical_formula_weight 719.91 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' P P 0.1023 0.0942 '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 '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 8.511 _cell_length_b 23.619(9) _cell_length_c 19.907(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.35(4) _cell_angle_gamma 90.00 _cell_volume 3776(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6993 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 28.78 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1532 _exptl_absorpt_coefficient_mu 0.374 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9666 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2009)' _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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32890 _diffrn_reflns_av_R_equivalents 0.0922 _diffrn_reflns_av_sigmaI/netI 0.1266 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8653 _reflns_number_gt 4477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0299P)^2^+11.1974P] 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 8653 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1617 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.1819 _refine_ls_wR_factor_gt 0.1684 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 -0.7257(2) 0.54875(7) -0.18483(9) 0.0469(4) Uani 1 1 d . . . S2 S -0.56375(19) 0.77579(6) -0.15600(8) 0.0349(4) Uani 1 1 d . . . S3 S 1.1818(2) 0.60129(6) 0.30616(8) 0.0427(4) Uani 1 1 d . . . S4 S 1.01734(19) 0.82377(6) 0.23033(8) 0.0358(4) Uani 1 1 d . . . P1 P -0.5422(2) 0.59629(6) -0.13667(8) 0.0347(4) Uani 1 1 d . . . P2 P 0.9911(2) 0.64575(6) 0.25674(8) 0.0332(4) Uani 1 1 d . . . O1 O -0.4872(5) 0.59973(16) -0.05331(19) 0.0343(9) Uani 1 1 d . . . O2 O -0.3644(5) 0.58267(16) -0.1413(2) 0.0389(10) Uani 1 1 d . . . O3 O 0.8324(5) 0.64325(15) 0.28104(19) 0.0358(10) Uani 1 1 d . . . O4 O 0.9080(5) 0.63308(15) 0.17456(19) 0.0354(9) Uani 1 1 d . . . N1 N -0.5799(6) 0.66350(18) -0.1644(2) 0.0367(12) Uani 1 1 d . . . H1A H -0.6743 0.6694 -0.1969 0.044 Uiso 1 1 calc R . . N2 N -0.3166(5) 0.70030(18) -0.1112(2) 0.0301(11) Uani 1 1 d . . . H2A H -0.2866 0.6654 -0.1101 0.036 Uiso 1 1 calc R . . N3 N 1.0319(6) 0.71491(17) 0.2644(2) 0.0307(11) Uani 1 1 d . . . H3A H 1.1302 0.7235 0.2921 0.037 Uiso 1 1 calc R . . N4 N 0.7685(6) 0.74901(19) 0.2099(2) 0.0317(11) Uani 1 1 d . . . H4A H 0.7396 0.7181 0.2254 0.038 Uiso 1 1 calc R . . C1 C -0.4799(7) 0.7109(2) -0.1423(3) 0.0286(12) Uani 1 1 d . . . C2 C -0.1858(7) 0.7406(2) -0.0794(3) 0.0303(13) Uani 1 1 d . . . C3 C -0.2076(7) 0.7832(2) -0.0367(3) 0.0327(13) Uani 1 1 d . . . H3B H -0.3069 0.7865 -0.0271 0.039 Uiso 1 1 calc R . . C4 C -0.0794(7) 0.8213(2) -0.0080(3) 0.0327(13) Uani 1 1 d . . . H4B H -0.0950 0.8509 0.0199 0.039 Uiso 1 1 calc R . . C5 C 0.0710(6) 0.8165(2) -0.0198(3) 0.0274(12) Uani 1 1 d . . . C6 C 0.0901(7) 0.7719(2) -0.0613(3) 0.0343(14) Uani 1 1 d . . . H6A H 0.1909 0.7674 -0.0695 0.041 Uiso 1 1 calc R . . C7 C -0.0375(7) 0.7335(2) -0.0911(3) 0.0309(13) Uani 1 1 d . . . H7A H -0.0224 0.7035 -0.1186 0.037 Uiso 1 1 calc R . . C8 C -0.6061(8) 0.6177(3) -0.0181(3) 0.0405(15) Uani 1 1 d . . . H8A H -0.7124 0.6274 -0.0544 0.049 Uiso 1 1 calc R . . C9 C -0.5346(8) 0.6695(3) 0.0252(3) 0.0476(17) Uani 1 1 d . . . H9A H -0.5224 0.6991 -0.0058 0.071 Uiso 1 1 calc R . . H9B H -0.4277 0.6606 0.0591 0.071 Uiso 1 1 calc R . . H9C H -0.6081 0.6820 0.0498 0.071 Uiso 1 1 calc R . . C10 C -0.6316(9) 0.5681(3) 0.0251(4) 0.0563(19) Uani 1 1 d . . . H10A H -0.6786 0.5369 -0.0061 0.084 Uiso 1 1 calc R . . H10B H -0.7060 0.5789 0.0501 0.084 Uiso 1 1 calc R . . H10C H -0.5265 0.5569 0.0587 0.084 Uiso 1 1 calc R . . C11 C -0.3341(9) 0.5457(2) -0.1952(3) 0.0449(17) Uani 1 1 d . . . H11A H -0.3967 0.5104 -0.1984 0.054 Uiso 1 1 calc R . . C12 C -0.3882(10) 0.5742(3) -0.2659(4) 0.067(2) Uani 1 1 d . . . H12A H -0.5061 0.5806 -0.2812 0.101 Uiso 1 1 calc R . . H12B H -0.3618 0.5506 -0.3000 0.101 Uiso 1 1 calc R . . H12C H -0.3314 0.6098 -0.2622 0.101 Uiso 1 1 calc R . . C13 C -0.1518(10) 0.5331(3) -0.1672(4) 0.072(2) Uani 1 1 d . . . H13A H -0.1250 0.5149 -0.1216 0.109 Uiso 1 1 calc R . . H13B H -0.0901 0.5678 -0.1621 0.109 Uiso 1 1 calc R . . H13C H -0.1231 0.5086 -0.1998 0.109 Uiso 1 1 calc R . . C14 C 0.2111(7) 0.8591(2) 0.0112(3) 0.0346(14) Uani 1 1 d . . . H14A H 0.2441 0.8749 -0.0271 0.042 Uiso 1 1 calc R . . H14B H 0.1706 0.8898 0.0333 0.042 Uiso 1 1 calc R . . C15 C 0.9334(7) 0.7604(2) 0.2336(3) 0.0322(14) Uani 1 1 d . . . C16 C 0.6374(6) 0.7809(2) 0.1633(3) 0.0249(12) Uani 1 1 d . . . C17 C 0.6536(7) 0.8107(2) 0.1062(3) 0.0282(12) Uani 1 1 d . . . H17A H 0.7571 0.8136 0.1001 0.034 Uiso 1 1 calc R . . C18 C 0.5170(7) 0.8361(2) 0.0585(3) 0.0299(13) Uani 1 1 d . . . H18A H 0.5303 0.8562 0.0206 0.036 Uiso 1 1 calc R . . C19 C 0.3588(7) 0.8328(2) 0.0648(3) 0.0309(13) Uani 1 1 d . . . C20 C 0.3469(7) 0.8037(2) 0.1239(3) 0.0308(13) Uani 1 1 d . . . H20A H 0.2444 0.8020 0.1311 0.037 Uiso 1 1 calc R . . C21 C 0.4811(7) 0.7775(2) 0.1717(3) 0.0323(13) Uani 1 1 d . . . H21A H 0.4683 0.7574 0.2097 0.039 Uiso 1 1 calc R . . C22 C 0.7316(9) 0.5918(2) 0.2735(3) 0.0452(17) Uani 1 1 d . . . H22A H 0.7762 0.5619 0.2509 0.054 Uiso 1 1 calc R . . C23 C 0.5593(9) 0.6077(3) 0.2267(4) 0.063(2) Uani 1 1 d . . . H23A H 0.5618 0.6185 0.1806 0.095 Uiso 1 1 calc R . . H23B H 0.5197 0.6388 0.2476 0.095 Uiso 1 1 calc R . . H23C H 0.4862 0.5759 0.2220 0.095 Uiso 1 1 calc R . . C24 C 0.7390(10) 0.5736(3) 0.3464(4) 0.068(2) Uani 1 1 d . . . H24A H 0.8514 0.5637 0.3737 0.101 Uiso 1 1 calc R . . H24B H 0.6679 0.5414 0.3428 0.101 Uiso 1 1 calc R . . H24C H 0.7025 0.6041 0.3695 0.101 Uiso 1 1 calc R . . C25 C 1.0087(7) 0.6229(2) 0.1281(3) 0.0351(14) Uani 1 1 d . . . H25A H 1.1068 0.6004 0.1542 0.042 Uiso 1 1 calc R . . C26 C 0.9001(8) 0.5887(3) 0.0663(3) 0.062(2) Uani 1 1 d . . . H26A H 0.8707 0.5536 0.0835 0.092 Uiso 1 1 calc R . . H26B H 0.9596 0.5810 0.0339 0.092 Uiso 1 1 calc R . . H26C H 0.8008 0.6097 0.0421 0.092 Uiso 1 1 calc R . . C27 C 1.0649(11) 0.6789(3) 0.1079(4) 0.080(3) Uani 1 1 d . . . H27A H 1.1342 0.6978 0.1499 0.119 Uiso 1 1 calc R . . H27B H 0.9694 0.7019 0.0846 0.119 Uiso 1 1 calc R . . H27C H 1.1269 0.6726 0.0761 0.119 Uiso 1 1 calc R . . C28 C 0.8693(15) 0.9609(4) 0.0947(5) 0.076(3) Uani 1 1 d . . . H28A H 0.831(7) 0.927(3) 0.116(3) 0.047(19) Uiso 1 1 d . . . H28B H 0.883(8) 0.995(3) 0.126(4) 0.07(2) Uiso 1 1 d . . . H28C H 0.987(12) 0.951(4) 0.092(5) 0.13(4) Uiso 1 1 d . . . C29 C 0.7328(11) 0.9752(3) 0.0268(5) 0.060(2) Uani 1 1 d . . . H29A H 0.716(6) 0.942(2) -0.006(3) 0.036(15) Uiso 1 1 d . . . H29B H 0.782(10) 1.003(4) 0.002(4) 0.11(3) Uiso 1 1 d . . . C30 C 0.5676(11) 0.9937(3) 0.0338(4) 0.062(2) Uani 1 1 d . . . H30A H 0.545(7) 0.964(2) 0.062(3) 0.038(16) Uiso 1 1 d . . . H30B H 0.601(8) 1.027(3) 0.064(3) 0.06(2) 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 S1 0.0484(10) 0.0343(9) 0.0517(10) -0.0118(8) 0.0082(8) -0.0075(8) S2 0.0419(9) 0.0291(8) 0.0306(8) -0.0016(6) 0.0078(7) -0.0008(7) S3 0.0567(11) 0.0300(8) 0.0343(9) 0.0068(7) 0.0056(8) 0.0039(8) S4 0.0371(9) 0.0268(7) 0.0380(9) 0.0058(6) 0.0051(7) -0.0019(7) P1 0.0385(9) 0.0292(8) 0.0334(9) -0.0066(7) 0.0079(7) 0.0000(7) P2 0.0454(10) 0.0270(8) 0.0253(8) 0.0038(6) 0.0091(7) -0.0023(7) O1 0.034(2) 0.038(2) 0.031(2) -0.0036(18) 0.0112(18) 0.0015(19) O2 0.037(2) 0.037(2) 0.042(3) -0.0116(19) 0.013(2) 0.0008(19) O3 0.051(3) 0.026(2) 0.032(2) 0.0005(17) 0.017(2) -0.0097(19) O4 0.045(2) 0.034(2) 0.027(2) 0.0006(17) 0.0126(19) 0.0030(19) N1 0.044(3) 0.032(3) 0.024(3) -0.003(2) -0.002(2) -0.004(2) N2 0.028(3) 0.030(3) 0.028(3) -0.004(2) 0.005(2) 0.004(2) N3 0.031(3) 0.026(2) 0.028(3) 0.004(2) 0.001(2) 0.001(2) N4 0.035(3) 0.028(2) 0.029(3) 0.008(2) 0.006(2) 0.002(2) C1 0.033(3) 0.030(3) 0.024(3) -0.004(2) 0.010(3) -0.001(3) C2 0.037(3) 0.029(3) 0.024(3) -0.001(2) 0.009(3) -0.004(3) C3 0.028(3) 0.039(3) 0.029(3) -0.006(3) 0.007(3) 0.002(3) C4 0.037(3) 0.028(3) 0.033(3) -0.006(2) 0.010(3) 0.000(3) C5 0.028(3) 0.027(3) 0.023(3) 0.004(2) 0.002(2) -0.002(2) C6 0.033(3) 0.038(3) 0.032(3) 0.001(3) 0.012(3) -0.002(3) C7 0.037(3) 0.032(3) 0.021(3) -0.004(2) 0.008(3) 0.005(3) C8 0.037(4) 0.045(4) 0.041(4) -0.006(3) 0.016(3) 0.002(3) C9 0.061(4) 0.044(4) 0.043(4) -0.010(3) 0.025(3) 0.000(3) C10 0.071(5) 0.048(4) 0.060(5) -0.008(3) 0.036(4) -0.012(4) C11 0.072(5) 0.025(3) 0.046(4) -0.010(3) 0.031(4) -0.006(3) C12 0.073(5) 0.093(6) 0.041(4) 0.006(4) 0.025(4) -0.002(5) C13 0.091(6) 0.062(5) 0.076(6) 0.004(4) 0.044(5) 0.039(5) C14 0.039(4) 0.030(3) 0.035(3) 0.003(3) 0.013(3) 0.003(3) C15 0.045(4) 0.031(3) 0.019(3) 0.003(2) 0.009(3) 0.004(3) C16 0.021(3) 0.025(3) 0.025(3) -0.001(2) 0.003(2) 0.001(2) C17 0.024(3) 0.032(3) 0.026(3) -0.002(2) 0.005(2) -0.002(2) C18 0.038(3) 0.029(3) 0.022(3) 0.000(2) 0.009(3) -0.005(3) C19 0.044(4) 0.022(3) 0.024(3) -0.003(2) 0.007(3) -0.007(3) C20 0.024(3) 0.037(3) 0.033(3) -0.001(3) 0.013(3) -0.009(3) C21 0.042(4) 0.031(3) 0.027(3) 0.003(2) 0.015(3) -0.006(3) C22 0.069(5) 0.030(3) 0.043(4) -0.008(3) 0.026(4) -0.014(3) C23 0.075(5) 0.055(5) 0.063(5) -0.010(4) 0.026(4) -0.036(4) C24 0.106(7) 0.052(4) 0.052(5) 0.009(4) 0.036(5) -0.018(4) C25 0.037(4) 0.039(3) 0.027(3) 0.000(3) 0.008(3) 0.000(3) C26 0.052(4) 0.091(6) 0.036(4) -0.020(4) 0.007(3) 0.016(4) C27 0.138(8) 0.057(5) 0.072(5) 0.010(4) 0.073(6) -0.001(5) C28 0.110(9) 0.047(5) 0.069(6) -0.023(5) 0.026(6) -0.006(5) C29 0.095(7) 0.034(4) 0.068(6) -0.010(4) 0.049(5) -0.005(4) C30 0.116(8) 0.028(4) 0.048(4) -0.007(4) 0.034(5) -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 S1 P1 1.904(2) . ? S2 C1 1.675(5) . ? S3 P2 1.909(2) . ? S4 C15 1.669(6) . ? P1 O1 1.570(4) . ? P1 O2 1.580(4) . ? P1 N1 1.676(5) . ? P2 O3 1.580(4) . ? P2 O4 1.581(4) . ? P2 N3 1.666(4) . ? O1 C8 1.471(6) . ? O2 C11 1.470(6) . ? O3 C22 1.466(7) . ? O4 C25 1.473(6) . ? N1 C1 1.386(6) . ? N1 H1A 0.8600 . ? N2 C1 1.345(6) . ? N2 C2 1.442(7) . ? N2 H2A 0.8600 . ? N3 C15 1.375(6) . ? N3 H3A 0.8600 . ? N4 C15 1.351(7) . ? N4 C16 1.409(6) . ? N4 H4A 0.8600 . ? C2 C7 1.368(7) . ? C2 C3 1.368(7) . ? C3 C4 1.382(7) . ? C3 H3B 0.9300 . ? C4 C5 1.380(7) . ? C4 H4B 0.9300 . ? C5 C6 1.383(7) . ? C5 C14 1.524(7) . ? C6 C7 1.387(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.505(8) . ? C8 C10 1.511(8) . ? C8 H8A 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.490(9) . ? C11 C13 1.494(9) . ? C11 H11A 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.488(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 C17 1.383(7) . ? C16 C21 1.397(7) . ? C17 C18 1.372(7) . ? C17 H17A 0.9300 . ? C18 C19 1.395(8) . ? C18 H18A 0.9300 . ? C19 C20 1.396(7) . ? C20 C21 1.369(7) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 C24 1.494(8) . ? C22 C23 1.501(9) . ? C22 H22A 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.506(8) . ? C25 C27 1.506(8) . ? C25 H25A 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.500(12) . ? C28 H28A 1.02(6) . ? C28 H28B 1.01(7) . ? C28 H28C 1.04(10) . ? C29 C30 1.523(11) . ? C29 H29A 1.00(5) . ? C29 H29B 0.99(9) . ? C30 C30 1.483(15) 3_675 ? C30 H30A 0.96(6) . ? C30 H30B 0.97(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 O1 P1 O2 96.7(2) . . ? O1 P1 N1 104.9(2) . . ? O2 P1 N1 104.8(2) . . ? O1 P1 S1 118.06(18) . . ? O2 P1 S1 119.48(17) . . ? N1 P1 S1 110.92(19) . . ? O3 P2 O4 100.1(2) . . ? O3 P2 N3 100.5(2) . . ? O4 P2 N3 106.8(2) . . ? O3 P2 S3 119.25(16) . . ? O4 P2 S3 116.19(17) . . ? N3 P2 S3 112.11(18) . . ? C8 O1 P1 120.4(4) . . ? C11 O2 P1 124.5(4) . . ? C22 O3 P2 122.0(4) . . ? C25 O4 P2 121.8(3) . . ? C1 N1 P1 129.0(4) . . ? C1 N1 H1A 115.5 . . ? P1 N1 H1A 115.5 . . ? C1 N2 C2 127.5(5) . . ? C1 N2 H2A 116.2 . . ? C2 N2 H2A 116.2 . . ? C15 N3 P2 130.3(4) . . ? C15 N3 H3A 114.8 . . ? P2 N3 H3A 114.8 . . ? C15 N4 C16 128.9(5) . . ? C15 N4 H4A 115.5 . . ? C16 N4 H4A 115.5 . . ? N2 C1 N1 115.4(5) . . ? N2 C1 S2 124.4(4) . . ? N1 C1 S2 120.2(4) . . ? C7 C2 C3 121.3(5) . . ? C7 C2 N2 117.8(5) . . ? C3 C2 N2 120.9(5) . . ? C2 C3 C4 118.9(5) . . ? C2 C3 H3B 120.5 . . ? C4 C3 H3B 120.5 . . ? C5 C4 C3 121.8(5) . . ? C5 C4 H4B 119.1 . . ? C3 C4 H4B 119.1 . . ? C4 C5 C6 117.6(5) . . ? C4 C5 C14 121.6(5) . . ? C6 C5 C14 120.8(5) . . ? C5 C6 C7 121.6(5) . . ? C5 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C2 C7 C6 118.9(5) . . ? C2 C7 H7A 120.6 . . ? C6 C7 H7A 120.6 . . ? O1 C8 C9 107.2(5) . . ? O1 C8 C10 107.4(5) . . ? C9 C8 C10 114.3(5) . . ? O1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C10 C8 H8A 109.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C12 110.3(5) . . ? O2 C11 C13 104.9(5) . . ? C12 C11 C13 113.5(6) . . ? O2 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C13 C11 H11A 109.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C5 112.2(4) . . ? C19 C14 H14A 109.2 . . ? C5 C14 H14A 109.2 . . ? C19 C14 H14B 109.2 . . ? C5 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N4 C15 N3 114.2(5) . . ? N4 C15 S4 125.0(4) . . ? N3 C15 S4 120.8(4) . . ? C17 C16 C21 119.1(5) . . ? C17 C16 N4 122.7(5) . . ? C21 C16 N4 117.9(5) . . ? C18 C17 C16 120.0(5) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C19 122.4(5) . . ? C17 C18 H18A 118.8 . . ? C19 C18 H18A 118.8 . . ? C18 C19 C20 116.4(5) . . ? C18 C19 C14 121.6(5) . . ? C20 C19 C14 122.0(5) . . ? C21 C20 C19 122.1(5) . . ? C21 C20 H20A 118.9 . . ? C19 C20 H20A 118.9 . . ? C20 C21 C16 120.0(5) . . ? C20 C21 H21A 120.0 . . ? C16 C21 H21A 120.0 . . ? O3 C22 C24 107.7(5) . . ? O3 C22 C23 105.9(5) . . ? C24 C22 C23 113.1(6) . . ? O3 C22 H22A 110.0 . . ? C24 C22 H22A 110.0 . . ? C23 C22 H22A 110.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O4 C25 C26 105.9(5) . . ? O4 C25 C27 109.1(5) . . ? C26 C25 C27 114.5(6) . . ? O4 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C27 C25 H25A 109.1 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 H28A 107(4) . . ? C29 C28 H28B 106(4) . . ? H28A C28 H28B 111(5) . . ? C29 C28 H28C 119(5) . . ? H28A C28 H28C 106(6) . . ? H28B C28 H28C 107(7) . . ? C28 C29 C30 116.4(7) . . ? C28 C29 H29A 109(3) . . ? C30 C29 H29A 111(3) . . ? C28 C29 H29B 106(5) . . ? C30 C29 H29B 114(5) . . ? H29A C29 H29B 100(6) . . ? C30 C30 C29 115.8(8) 3_675 . ? C30 C30 H30A 116(4) 3_675 . ? C29 C30 H30A 103(3) . . ? C30 C30 H30B 113(4) 3_675 . ? C29 C30 H30B 101(4) . . ? H30A C30 H30B 107(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C8 173.8(4) . . . . ? N1 P1 O1 C8 66.4(4) . . . . ? S1 P1 O1 C8 -57.6(4) . . . . ? O1 P1 O2 C11 145.2(4) . . . . ? N1 P1 O2 C11 -107.4(4) . . . . ? S1 P1 O2 C11 17.6(5) . . . . ? O4 P2 O3 C22 61.3(4) . . . . ? N3 P2 O3 C22 170.6(4) . . . . ? S3 P2 O3 C22 -66.6(4) . . . . ? O3 P2 O4 C25 -171.4(4) . . . . ? N3 P2 O4 C25 84.3(4) . . . . ? S3 P2 O4 C25 -41.6(4) . . . . ? O1 P1 N1 C1 50.7(5) . . . . ? O2 P1 N1 C1 -50.6(5) . . . . ? S1 P1 N1 C1 179.1(4) . . . . ? O3 P2 N3 C15 -57.0(5) . . . . ? O4 P2 N3 C15 47.0(5) . . . . ? S3 P2 N3 C15 175.3(4) . . . . ? C2 N2 C1 N1 -176.1(5) . . . . ? C2 N2 C1 S2 4.9(8) . . . . ? P1 N1 C1 N2 21.6(7) . . . . ? P1 N1 C1 S2 -159.4(3) . . . . ? C1 N2 C2 C7 -139.3(6) . . . . ? C1 N2 C2 C3 43.3(8) . . . . ? C7 C2 C3 C4 3.4(8) . . . . ? N2 C2 C3 C4 -179.3(5) . . . . ? C2 C3 C4 C5 -1.8(8) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? C3 C4 C5 C14 179.2(5) . . . . ? C4 C5 C6 C7 0.9(8) . . . . ? C14 C5 C6 C7 -178.6(5) . . . . ? C3 C2 C7 C6 -2.8(8) . . . . ? N2 C2 C7 C6 179.8(5) . . . . ? C5 C6 C7 C2 0.6(8) . . . . ? P1 O1 C8 C9 -120.7(4) . . . . ? P1 O1 C8 C10 116.1(5) . . . . ? P1 O2 C11 C12 72.3(6) . . . . ? P1 O2 C11 C13 -165.0(4) . . . . ? C4 C5 C14 C19 114.3(6) . . . . ? C6 C5 C14 C19 -66.2(7) . . . . ? C16 N4 C15 N3 -165.1(5) . . . . ? C16 N4 C15 S4 17.3(8) . . . . ? P2 N3 C15 N4 20.3(7) . . . . ? P2 N3 C15 S4 -162.0(3) . . . . ? C15 N4 C16 C17 36.2(8) . . . . ? C15 N4 C16 C21 -150.0(5) . . . . ? C21 C16 C17 C18 -0.5(8) . . . . ? N4 C16 C17 C18 173.3(5) . . . . ? C16 C17 C18 C19 -0.4(8) . . . . ? C17 C18 C19 C20 2.0(8) . . . . ? C17 C18 C19 C14 -178.0(5) . . . . ? C5 C14 C19 C18 124.9(5) . . . . ? C5 C14 C19 C20 -55.0(7) . . . . ? C18 C19 C20 C21 -2.8(8) . . . . ? C14 C19 C20 C21 177.2(5) . . . . ? C19 C20 C21 C16 2.0(8) . . . . ? C17 C16 C21 C20 -0.3(8) . . . . ? N4 C16 C21 C20 -174.3(5) . . . . ? P2 O3 C22 C24 118.2(5) . . . . ? P2 O3 C22 C23 -120.5(5) . . . . ? P2 O4 C25 C26 155.9(4) . . . . ? P2 O4 C25 C27 -80.4(6) . . . . ? C28 C29 C30 C30 -178.3(8) . . . 3_675 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A S4 0.86 2.55 3.387(5) 165.5 4_375 N3 H3A S2 0.86 2.46 3.285(5) 160.0 4_776 N2 H2A O2 0.86 2.09 2.843(6) 145.6 . N4 H4A O3 0.86 2.10 2.834(6) 143.4 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.350 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.078 # Attachment '- 6.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 844832' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H40 N4 O5 P2 S4, 0.24(C2 H4 Cl4), 0.36(C Cl2), 0.71(H)' _chemical_formula_sum 'C26.83 H41.66 Cl1.67 N4 O5 P2 S4' _chemical_formula_weight 749.58 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' P P 0.1023 0.0942 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.051(11) _cell_length_b 15.013(8) _cell_length_c 15.837(8) _cell_angle_alpha 90.00 _cell_angle_beta 131.65(3) _cell_angle_gamma 90.00 _cell_volume 3740(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3797 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 36.79 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1572 _exptl_absorpt_coefficient_mu 0.498 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9878 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2009)' _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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15187 _diffrn_reflns_av_R_equivalents 0.0773 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4278 _reflns_number_gt 2283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1254P)^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 4278 _refine_ls_number_parameters 209 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1396 _refine_ls_R_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.2232 _refine_ls_wR_factor_gt 0.2027 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.17476(8) -0.05610(9) 0.57486(11) 0.0396(4) Uani 1 1 d . . . S2 S 0.16321(9) 0.29190(9) 0.51284(13) 0.0458(4) Uani 1 1 d . . . P1 P 0.25478(8) 0.02492(9) 0.59624(10) 0.0307(3) Uani 1 1 d . . . O1 O 0.3312(2) 0.0408(2) 0.7246(3) 0.0343(8) Uani 1 1 d . . . O2 O 0.2976(2) -0.0020(2) 0.5482(3) 0.0344(8) Uani 1 1 d . B . O3 O 0.0000 0.3191(3) 0.7500 0.0426(13) Uani 1 2 d S . . N1 N 0.2153(2) 0.1262(3) 0.5369(3) 0.0305(9) Uani 1 1 d . . . H1A H 0.2216 0.1429 0.4910 0.037 Uiso 1 1 d R . . N2 N 0.1427(2) 0.1512(3) 0.5959(3) 0.0294(9) Uani 1 1 d . . . H2A H 0.1457 0.0942 0.6034 0.035 Uiso 1 1 d R . . C1 C 0.1735(3) 0.1855(3) 0.5518(4) 0.0318(11) Uani 1 1 d . . . C2 C 0.1045(3) 0.1972(3) 0.6315(4) 0.0269(10) Uani 1 1 d . . . C3 C 0.1380(3) 0.2761(3) 0.6930(4) 0.0343(11) Uani 1 1 d . . . H3A H 0.1838 0.3035 0.7070 0.041 Uiso 1 1 calc R . . C4 C 0.1026(3) 0.3126(3) 0.7325(4) 0.0379(12) Uani 1 1 d . . . H4A H 0.1254 0.3650 0.7745 0.045 Uiso 1 1 calc R . . C5 C 0.0337(3) 0.2736(3) 0.7116(4) 0.0325(11) Uani 1 1 d . . . C6 C 0.0000(3) 0.1961(3) 0.6505(4) 0.0357(12) Uani 1 1 d . . . H6A H -0.0460 0.1694 0.6367 0.043 Uiso 1 1 calc R . . C7 C 0.0351(3) 0.1575(3) 0.6093(4) 0.0329(11) Uani 1 1 d . . . H7A H 0.0120 0.1053 0.5670 0.039 Uiso 1 1 calc R . . C8 C 0.4051(3) 0.0984(4) 0.7726(4) 0.0358(12) Uani 1 1 d . . . H8A H 0.4028 0.1191 0.7118 0.043 Uiso 1 1 calc R . . C9 C 0.4820(4) 0.0422(5) 0.8524(5) 0.0642(19) Uani 1 1 d . . . H9A H 0.4806 -0.0067 0.8121 0.096 Uiso 1 1 calc R . . H9B H 0.4831 0.0196 0.9101 0.096 Uiso 1 1 calc R . . H9C H 0.5320 0.0773 0.8866 0.096 Uiso 1 1 calc R . . C10 C 0.4004(4) 0.1771(5) 0.8267(6) 0.074(2) Uani 1 1 d . . . H10A H 0.3455 0.2045 0.7734 0.112 Uiso 1 1 calc R . . H10B H 0.4436 0.2194 0.8498 0.112 Uiso 1 1 calc R . . H10C H 0.4091 0.1577 0.8915 0.112 Uiso 1 1 calc R . . C11 C 0.2523(4) -0.0558(4) 0.4425(4) 0.0491(15) Uani 1 1 d . . . H11A H 0.1924 -0.0672 0.4029 0.059 Uiso 1 1 calc R A 1 C12 C 0.2655(5) -0.0110(6) 0.3716(6) 0.089(3) Uani 1 1 d . B . H12A H 0.2455 -0.0488 0.3093 0.134 Uiso 1 1 calc R . . H12B H 0.3250 0.0008 0.4164 0.134 Uiso 1 1 calc R . . H12C H 0.2346 0.0442 0.3434 0.134 Uiso 1 1 calc R . . C13A C 0.3079(15) -0.1433(9) 0.4843(11) 0.055(5) Uiso 0.52(4) 1 d P B 1 H13A H 0.3046 -0.1762 0.5333 0.083 Uiso 0.52(4) 1 calc PR B 1 H13B H 0.3660 -0.1274 0.5247 0.083 Uiso 0.52(4) 1 calc PR B 1 H13C H 0.2869 -0.1794 0.4203 0.083 Uiso 0.52(4) 1 calc PR B 1 C13B C 0.266(2) -0.1496(11) 0.4669(14) 0.067(6) Uiso 0.48(4) 1 d P B 2 H13D H 0.2180 -0.1748 0.4537 0.100 Uiso 0.48(4) 1 calc PR B 2 H13E H 0.3163 -0.1585 0.5446 0.100 Uiso 0.48(4) 1 calc PR B 2 H13F H 0.2724 -0.1783 0.4189 0.100 Uiso 0.48(4) 1 calc PR B 2 Cl1 Cl 0.0372(5) 0.0820(5) 0.2014(5) 0.083(3) Uiso 0.357(14) 1 d P C 3 C1S C 0.0000 0.1523(18) 0.2500 0.043(6) Uiso 0.357(14) 2 d SP . 3 H1SA H 0.0456 0.1900 0.3108 0.052 Uiso 0.178(7) 1 calc PR C 3 H1SB H -0.0456 0.1900 0.1892 0.052 Uiso 0.178(7) 1 calc PR C 3 Cl1S Cl 0.0141(6) 0.0478(6) 0.2153(7) 0.074(3) Uiso 0.238(8) 1 d PD . 4 Cl2S Cl -0.0629(6) 0.0916(5) 0.3079(6) 0.058(3) Uiso 0.238(8) 1 d PD . 4 C2S C -0.0122(13) 0.1324(13) 0.2643(17) 0.033(6) Uiso 0.238(8) 1 d PD . 4 H2SA H 0.0393 0.1630 0.3269 0.040 Uiso 0.238(8) 1 calc PR . 4 H2SB H -0.0488 0.1754 0.2043 0.040 Uiso 0.238(8) 1 calc PR . 4 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 0.0347(7) 0.0397(8) 0.0469(7) -0.0028(6) 0.0282(6) -0.0077(6) S2 0.0535(9) 0.0420(9) 0.0714(10) 0.0280(7) 0.0539(8) 0.0218(7) P1 0.0287(7) 0.0344(8) 0.0318(6) 0.0019(5) 0.0212(6) 0.0001(6) O1 0.0324(19) 0.037(2) 0.0343(17) 0.0018(14) 0.0225(16) -0.0017(15) O2 0.0362(19) 0.037(2) 0.0367(18) -0.0049(15) 0.0271(16) -0.0019(15) O3 0.064(3) 0.023(3) 0.078(4) 0.000 0.063(3) 0.000 N1 0.033(2) 0.037(2) 0.031(2) 0.0046(17) 0.0254(19) 0.0037(18) N2 0.034(2) 0.028(2) 0.039(2) 0.0029(17) 0.0297(19) 0.0026(18) C1 0.026(2) 0.042(3) 0.028(2) 0.006(2) 0.018(2) 0.007(2) C2 0.026(2) 0.030(3) 0.032(2) 0.0024(19) 0.022(2) 0.000(2) C3 0.035(3) 0.036(3) 0.040(3) -0.001(2) 0.028(2) -0.007(2) C4 0.047(3) 0.028(3) 0.058(3) -0.008(2) 0.043(3) -0.010(2) C5 0.037(3) 0.024(3) 0.049(3) 0.005(2) 0.034(3) 0.005(2) C6 0.032(3) 0.037(3) 0.053(3) -0.002(2) 0.034(3) -0.005(2) C7 0.034(3) 0.030(3) 0.048(3) -0.008(2) 0.033(2) -0.010(2) C8 0.028(3) 0.045(3) 0.031(2) -0.006(2) 0.018(2) -0.012(2) C9 0.040(3) 0.062(5) 0.063(4) 0.003(3) 0.023(3) -0.013(3) C10 0.058(4) 0.066(5) 0.096(5) -0.044(4) 0.049(4) -0.035(4) C11 0.055(4) 0.062(4) 0.039(3) -0.016(3) 0.035(3) -0.019(3) C12 0.114(7) 0.106(7) 0.059(4) -0.013(4) 0.063(5) -0.026(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 P1 1.917(2) . ? S2 C1 1.674(5) . ? P1 O1 1.559(4) . ? P1 O2 1.570(3) . ? P1 N1 1.688(4) . ? O1 C8 1.475(6) . ? O2 C11 1.497(6) . ? O3 C5 1.383(5) 2_556 ? O3 C5 1.383(5) . ? N1 C1 1.376(6) . ? N1 H1A 0.8591 . ? N2 C1 1.332(6) . ? N2 C2 1.429(6) . ? N2 H2A 0.8598 . ? C2 C7 1.391(6) . ? C2 C3 1.391(7) . ? C3 C4 1.367(7) . ? C3 H3A 0.9300 . ? C4 C5 1.386(7) . ? C4 H4A 0.9300 . ? C5 C6 1.371(7) . ? C6 C7 1.397(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.487(8) . ? C8 C10 1.501(8) . ? C8 H8A 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C13B 1.438(16) . ? C11 C12 1.486(9) . ? C11 C13A 1.583(16) . ? C11 H11A 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13A H13A 0.9600 . ? C13A H13B 0.9600 . ? C13A H13C 0.9600 . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 0.9600 . ? Cl1 C1S 1.766(17) . ? C1S Cl1 1.766(17) 2 ? C1S H1SA 0.9700 . ? C1S H1SB 0.9700 . ? Cl1S C2S 1.32(2) 2 ? Cl1S Cl2S 1.457(17) 2 ? Cl1S Cl1S 1.56(2) 2 ? Cl1S C2S 1.758(15) . ? Cl2S Cl1S 1.457(17) 2 ? Cl2S C2S 1.724(16) . ? C2S H2SA 0.9700 . ? C2S H2SB 0.9700 . ? 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 O1 P1 O2 104.16(19) . . ? O1 P1 N1 106.68(19) . . ? O2 P1 N1 101.01(19) . . ? O1 P1 S1 110.58(15) . . ? O2 P1 S1 118.12(15) . . ? N1 P1 S1 115.06(16) . . ? C8 O1 P1 125.6(3) . . ? C11 O2 P1 122.4(3) . . ? C5 O3 C5 120.9(5) 2_556 . ? C1 N1 P1 128.4(3) . . ? C1 N1 H1A 115.7 . . ? P1 N1 H1A 115.9 . . ? C1 N2 C2 128.1(4) . . ? C1 N2 H2A 116.1 . . ? C2 N2 H2A 115.8 . . ? N2 C1 N1 115.4(4) . . ? N2 C1 S2 125.0(4) . . ? N1 C1 S2 119.6(3) . . ? C7 C2 C3 120.0(4) . . ? C7 C2 N2 117.7(4) . . ? C3 C2 N2 122.1(4) . . ? C4 C3 C2 119.1(4) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 121.6(5) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C6 C5 O3 123.5(4) . . ? C6 C5 C4 119.8(4) . . ? O3 C5 C4 116.6(4) . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C2 C7 C6 119.9(4) . . ? C2 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? O1 C8 C9 106.6(4) . . ? O1 C8 C10 107.9(4) . . ? C9 C8 C10 114.2(5) . . ? O1 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C10 C8 H8A 109.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13B C11 C12 122.9(11) . . ? C13B C11 O2 111.3(8) . . ? C12 C11 O2 107.4(5) . . ? C13B C11 C13A 27.7(8) . . ? C12 C11 C13A 103.5(9) . . ? O2 C11 C13A 103.6(6) . . ? C13B C11 H11A 86.8 . . ? C12 C11 H11A 113.7 . . ? O2 C11 H11A 113.7 . . ? C13A C11 H11A 113.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13A H13A 109.5 . . ? C11 C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C11 C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C11 C13B H13D 109.5 . . ? C11 C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C11 C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? Cl1 C1S Cl1 106.6(15) 2 . ? Cl1 C1S H1SA 110.4 2 . ? Cl1 C1S H1SA 110.4 . . ? Cl1 C1S H1SB 110.4 2 . ? Cl1 C1S H1SB 110.4 . . ? H1SA C1S H1SB 108.6 . . ? C2S Cl1S Cl2S 76.6(9) 2 2 ? C2S Cl1S Cl1S 74.9(9) 2 2 ? Cl2S Cl1S Cl1S 147.2(6) 2 2 ? C2S Cl1S C2S 29.0(11) 2 . ? Cl2S Cl1S C2S 105.4(9) 2 . ? Cl1S Cl1S C2S 46.4(7) 2 . ? Cl1S Cl2S C2S 48.1(7) 2 . ? Cl2S C2S Cl1S 112.3(12) . . ? Cl2S C2S H2SA 109.1 . . ? Cl1S C2S H2SA 109.1 . . ? Cl2S C2S H2SB 109.1 . . ? Cl1S C2S H2SB 109.1 . . ? H2SA C2S H2SB 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C8 51.4(4) . . . . ? N1 P1 O1 C8 -54.9(4) . . . . ? S1 P1 O1 C8 179.3(3) . . . . ? O1 P1 O2 C11 156.0(4) . . . . ? N1 P1 O2 C11 -93.5(4) . . . . ? S1 P1 O2 C11 32.9(4) . . . . ? O1 P1 N1 C1 -68.3(4) . . . . ? O2 P1 N1 C1 -176.8(4) . . . . ? S1 P1 N1 C1 54.8(4) . . . . ? C2 N2 C1 N1 173.0(4) . . . . ? C2 N2 C1 S2 -8.1(7) . . . . ? P1 N1 C1 N2 -17.5(6) . . . . ? P1 N1 C1 S2 163.6(3) . . . . ? C1 N2 C2 C7 141.2(5) . . . . ? C1 N2 C2 C3 -43.1(7) . . . . ? C7 C2 C3 C4 1.1(7) . . . . ? N2 C2 C3 C4 -174.5(4) . . . . ? C2 C3 C4 C5 -0.8(8) . . . . ? C5 O3 C5 C6 37.4(4) 2_556 . . . ? C5 O3 C5 C4 -145.9(5) 2_556 . . . ? C3 C4 C5 C6 0.5(8) . . . . ? C3 C4 C5 O3 -176.4(4) . . . . ? O3 C5 C6 C7 176.2(4) . . . . ? C4 C5 C6 C7 -0.5(8) . . . . ? C3 C2 C7 C6 -1.1(7) . . . . ? N2 C2 C7 C6 174.7(4) . . . . ? C5 C6 C7 C2 0.8(7) . . . . ? P1 O1 C8 C9 -125.5(4) . . . . ? P1 O1 C8 C10 111.5(5) . . . . ? P1 O2 C11 C13B -90.2(15) . . . . ? P1 O2 C11 C12 132.6(5) . . . . ? P1 O2 C11 C13A -118.2(9) . . . . ? Cl1S Cl2S C2S Cl1S 15.1(9) 2 . . . ? C2S Cl1S C2S Cl2S 178(4) 2 . . . ? Cl2S Cl1S C2S Cl2S -174.9(9) 2 . . . ? Cl1S Cl1S C2S Cl2S -14.5(9) 2 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A S2 0.86 2.65 3.370(4) 141.7 7_556 N2 H2A S1 0.86 2.46 3.248(4) 153.2 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.935 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.106 # Attachment '- 8.cif' data_safin73 _database_code_depnum_ccdc_archive 'CCDC 844833' #TrackingRef '- 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H54 N4 O4 P2 S4' _chemical_formula_sum 'C27 H54 N4 O4 P2 S4' _chemical_formula_weight 684.89 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' P P 0.1023 0.0942 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 45.212(2) _cell_length_b 8.3601(4) _cell_length_c 19.7758(20) _cell_angle_alpha 90.00 _cell_angle_beta 105.821(7) _cell_angle_gamma 90.00 _cell_volume 7191.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6572 _cell_measurement_theta_min 1.8688 _cell_measurement_theta_max 25.3036 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2928 _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_T_min 0.69253 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '120 images, \D\F 2.0\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30648 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -54 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.36 _reflns_number_total 6562 _reflns_number_gt 5387 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+38.4419P] 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 6562 _refine_ls_number_parameters 408 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1638 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.16282(9) 0.6192(5) 0.6079(2) 0.0408(9) Uani 1 1 d . . . H1A H 0.1840 0.6182 0.6396 0.049 Uiso 1 1 calc R . . H1B H 0.1604 0.7199 0.5806 0.049 Uiso 1 1 calc R . . C2 C 0.15985(8) 0.4803(4) 0.55675(19) 0.0377(9) Uani 1 1 d . . . H2 H 0.1386 0.4817 0.5241 0.045 Uiso 1 1 calc R . . C3 C 0.16491(9) 0.3177(4) 0.59498(19) 0.0405(9) Uani 1 1 d . . . H3A H 0.1847 0.3206 0.6321 0.049 Uiso 1 1 calc R . . H3B H 0.1483 0.3004 0.6181 0.049 Uiso 1 1 calc R . . C4 C 0.16534(8) 0.1776(4) 0.54583(18) 0.0353(8) Uani 1 1 d . . . H4A H 0.1705 0.0778 0.5735 0.042 Uiso 1 1 calc R . . H4B H 0.1447 0.1645 0.5125 0.042 Uiso 1 1 calc R . . C5 C 0.18888(7) 0.2075(4) 0.50558(16) 0.0260(7) Uani 1 1 d . . . H5 H 0.2095 0.2180 0.5403 0.031 Uiso 1 1 calc R . . C6 C 0.18203(9) 0.3623(4) 0.46383(18) 0.0356(8) Uani 1 1 d . . . H6A H 0.1976 0.3794 0.4377 0.043 Uiso 1 1 calc R . . H6B H 0.1616 0.3555 0.4294 0.043 Uiso 1 1 calc R . . C7 C 0.18264(9) 0.5016(4) 0.5136(2) 0.0405(9) Uani 1 1 d . . . H7A H 0.2036 0.5121 0.5457 0.049 Uiso 1 1 calc R . . H7B H 0.1778 0.6016 0.4860 0.049 Uiso 1 1 calc R . . N8 N 0.19003(6) 0.0727(3) 0.45935(13) 0.0252(6) Uani 1 1 d . . . H8 H 0.1767 0.0708 0.4176 0.030 Uiso 1 1 calc R . . C9 C 0.21001(7) -0.0475(4) 0.47623(15) 0.0231(7) Uani 1 1 d . . . S10 S 0.23698(2) -0.05975(11) 0.55302(4) 0.0349(2) Uani 1 1 d . . . N11 N 0.20768(6) -0.1676(3) 0.42690(12) 0.0236(6) Uani 1 1 d . . . H11 H 0.2187 -0.2535 0.4421 0.028 Uiso 1 1 calc R . . P12 P 0.187013(17) -0.17404(9) 0.34286(4) 0.02072(17) Uani 1 1 d . . . S13 S 0.191940(19) -0.37680(10) 0.30273(4) 0.02915(19) Uani 1 1 d . . . O14 O 0.15334(4) -0.1191(2) 0.34165(11) 0.0245(5) Uani 1 1 d . . . C15 C 0.13014(7) -0.2325(4) 0.35219(18) 0.0310(8) Uani 1 1 d . . . H15 H 0.1401 -0.3373 0.3692 0.037 Uiso 1 1 calc R . . C16 C 0.11713(10) -0.1599(5) 0.4075(2) 0.0533(11) Uani 1 1 d . . . H16A H 0.1337 -0.1438 0.4508 0.080 Uiso 1 1 calc R . . H16B H 0.1016 -0.2318 0.4170 0.080 Uiso 1 1 calc R . . H16C H 0.1076 -0.0567 0.3909 0.080 Uiso 1 1 calc R . . C17 C 0.10697(9) -0.2547(5) 0.2826(2) 0.0461(10) Uani 1 1 d . . . H17A H 0.0965 -0.1530 0.2673 0.069 Uiso 1 1 calc R . . H17B H 0.0919 -0.3352 0.2870 0.069 Uiso 1 1 calc R . . H17C H 0.1174 -0.2906 0.2478 0.069 Uiso 1 1 calc R . . O18 O 0.19513(4) -0.0178(3) 0.30797(10) 0.0242(5) Uani 1 1 d . . . C19 C 0.22687(7) 0.0074(5) 0.30328(19) 0.0356(8) Uani 1 1 d . . . H19 H 0.2401 -0.0845 0.3257 0.043 Uiso 1 1 calc R . . C20 C 0.23827(9) 0.1586(5) 0.3430(2) 0.0530(11) Uani 1 1 d . . . H20A H 0.2252 0.2483 0.3213 0.079 Uiso 1 1 calc R . . H20B H 0.2595 0.1792 0.3419 0.079 Uiso 1 1 calc R . . H20C H 0.2376 0.1469 0.3919 0.079 Uiso 1 1 calc R . . C21 C 0.22564(9) 0.0160(6) 0.2272(2) 0.0518(11) Uani 1 1 d . . . H21A H 0.2164 -0.0824 0.2036 0.078 Uiso 1 1 calc R . . H21B H 0.2465 0.0279 0.2222 0.078 Uiso 1 1 calc R . . H21C H 0.2132 0.1080 0.2057 0.078 Uiso 1 1 calc R . . C22 C 0.14062(8) 0.6230(5) 0.6528(2) 0.0393(9) Uani 1 1 d . . . H22 H 0.1414 0.5165 0.6762 0.047 Uiso 1 1 calc R . . C23 C 0.10696(9) 0.6548(5) 0.6101(2) 0.0444(10) Uani 1 1 d . . . H23A H 0.1058 0.7591 0.5859 0.053 Uiso 1 1 calc R . . H23B H 0.1004 0.5708 0.5738 0.053 Uiso 1 1 calc R . . C24 C 0.08524(8) 0.6561(4) 0.65697(19) 0.0374(9) Uani 1 1 d . . . H24A H 0.0642 0.6827 0.6284 0.045 Uiso 1 1 calc R . . H24B H 0.0847 0.5483 0.6773 0.045 Uiso 1 1 calc R . . C25 C 0.09549(7) 0.7771(4) 0.71576(18) 0.0331(8) Uani 1 1 d . . . H25 H 0.0933 0.8871 0.6951 0.040 Uiso 1 1 calc R . . C26 C 0.12914(8) 0.7502(5) 0.7569(2) 0.0410(9) Uani 1 1 d . . . H26A H 0.1357 0.8362 0.7923 0.049 Uiso 1 1 calc R . . H26B H 0.1310 0.6470 0.7822 0.049 Uiso 1 1 calc R . . C27 C 0.15007(8) 0.7490(5) 0.7094(2) 0.0438(10) Uani 1 1 d . . . H27A H 0.1714 0.7281 0.7377 0.053 Uiso 1 1 calc R . . H27B H 0.1496 0.8555 0.6873 0.053 Uiso 1 1 calc R . . N28 N 0.07751(6) 0.7664(3) 0.76627(15) 0.0334(7) Uani 1 1 d . . . H28 H 0.0853 0.7075 0.8038 0.040 Uiso 1 1 calc R . . C29 C 0.05079(7) 0.8350(4) 0.76213(18) 0.0307(8) Uani 1 1 d . . . S30 S 0.03267(2) 0.95529(12) 0.69567(5) 0.0407(2) Uani 1 1 d . . . N31 N 0.03753(6) 0.8083(4) 0.81675(15) 0.0348(7) Uani 1 1 d . . . H31 H 0.0209 0.8663 0.8130 0.042 Uiso 1 1 calc R . . P32 P 0.04578(2) 0.69212(14) 0.88759(5) 0.0419(3) Uani 1 1 d . A . S33 S 0.08524(3) 0.59013(15) 0.90971(6) 0.0545(3) Uani 1 1 d . . . O34 O 0.03877(8) 0.7927(5) 0.94670(16) 0.0687(10) Uani 1 1 d . . . C35 C 0.05967(14) 0.9127(7) 0.9841(3) 0.0786(17) Uani 1 1 d . . . H35 H 0.0747 0.9373 0.9568 0.094 Uiso 1 1 calc R . . C36 C 0.07685(13) 0.8575(7) 1.0545(3) 0.0768(16) Uani 1 1 d . . . H36A H 0.0624 0.8336 1.0822 0.115 Uiso 1 1 calc R . . H36B H 0.0911 0.9413 1.0780 0.115 Uiso 1 1 calc R . . H36C H 0.0884 0.7607 1.0502 0.115 Uiso 1 1 calc R . . C37 C 0.0415(2) 1.0620(10) 0.9876(5) 0.179(5) Uani 1 1 d . . . H37A H 0.0334 1.1059 0.9402 0.269 Uiso 1 1 calc R . . H37B H 0.0549 1.1412 1.0175 0.269 Uiso 1 1 calc R . . H37C H 0.0244 1.0360 1.0073 0.269 Uiso 1 1 calc R . . O38 O 0.01734(7) 0.5777(4) 0.87470(18) 0.0688(9) Uani 1 1 d U . . C39 C 0.0143(3) 0.4540(14) 0.9155(6) 0.078(3) Uani 0.509(5) 1 d PU A 1 H39 H 0.0334 0.3875 0.9271 0.094 Uiso 0.509(5) 1 calc PR A 1 C40 C 0.0064(5) 0.501(2) 0.9810(9) 0.174(8) Uani 0.509(5) 1 d PU A 1 H40A H 0.0208 0.5829 1.0058 0.261 Uiso 0.509(5) 1 calc PR A 1 H40B H 0.0076 0.4072 1.0113 0.261 Uiso 0.509(5) 1 calc PR A 1 H40C H -0.0146 0.5442 0.9689 0.261 Uiso 0.509(5) 1 calc PR A 1 C41 C -0.0123(3) 0.3581(15) 0.8750(8) 0.097(4) Uani 0.509(5) 1 d PU A 1 H41A H -0.0305 0.4264 0.8612 0.145 Uiso 0.509(5) 1 calc PR A 1 H41B H -0.0160 0.2701 0.9043 0.145 Uiso 0.509(5) 1 calc PR A 1 H41C H -0.0078 0.3146 0.8329 0.145 Uiso 0.509(5) 1 calc PR A 1 C51 C 0.0124(2) 0.4401(12) 0.8197(6) 0.070(3) Uani 0.491(5) 1 d PU A 2 H51 H 0.0205 0.4745 0.7796 0.084 Uiso 0.491(5) 1 calc PR A 2 C52 C -0.0209(2) 0.4250(13) 0.7951(8) 0.085(4) Uani 0.491(5) 1 d PU A 2 H52A H -0.0263 0.3447 0.7576 0.128 Uiso 0.491(5) 1 calc PR A 2 H52B H -0.0299 0.5283 0.7769 0.128 Uiso 0.491(5) 1 calc PR A 2 H52C H -0.0290 0.3919 0.8342 0.128 Uiso 0.491(5) 1 calc PR A 2 C53 C 0.0277(3) 0.2855(15) 0.8493(11) 0.133(7) Uani 0.491(5) 1 d PU A 2 H53A H 0.0174 0.2414 0.8829 0.199 Uiso 0.491(5) 1 calc PR A 2 H53B H 0.0494 0.3056 0.8734 0.199 Uiso 0.491(5) 1 calc PR A 2 H53C H 0.0263 0.2088 0.8111 0.199 Uiso 0.491(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.042(2) 0.0361(19) 0.042(2) -0.0045(16) 0.0072(16) 0.0040(16) C2 0.0399(19) 0.0316(18) 0.0350(19) -0.0032(15) -0.0012(15) 0.0077(15) C3 0.047(2) 0.040(2) 0.0388(19) -0.0096(16) 0.0194(16) 0.0017(17) C4 0.0438(19) 0.0295(17) 0.0363(18) -0.0052(15) 0.0171(15) 0.0041(15) C5 0.0294(15) 0.0235(15) 0.0216(15) -0.0047(12) 0.0008(12) 0.0065(13) C6 0.047(2) 0.0314(18) 0.0277(17) 0.0026(14) 0.0092(15) 0.0077(16) C7 0.058(2) 0.0275(17) 0.040(2) 0.0010(15) 0.0191(17) 0.0062(17) N8 0.0251(12) 0.0276(14) 0.0192(12) -0.0035(10) 0.0000(10) 0.0085(11) C9 0.0242(14) 0.0268(15) 0.0187(14) -0.0010(12) 0.0068(11) 0.0027(12) S10 0.0407(5) 0.0376(5) 0.0187(4) -0.0069(3) -0.0050(3) 0.0179(4) N11 0.0288(13) 0.0210(12) 0.0175(12) -0.0019(10) 0.0003(10) 0.0056(11) P12 0.0205(4) 0.0232(4) 0.0165(3) -0.0014(3) 0.0018(3) 0.0013(3) S13 0.0315(4) 0.0280(4) 0.0247(4) -0.0081(3) 0.0022(3) 0.0030(3) O14 0.0210(10) 0.0233(11) 0.0275(11) -0.0008(9) 0.0039(8) -0.0003(9) C15 0.0285(16) 0.0280(17) 0.0366(18) 0.0031(14) 0.0093(14) -0.0031(14) C16 0.058(2) 0.051(2) 0.064(3) -0.012(2) 0.039(2) -0.015(2) C17 0.0334(18) 0.047(2) 0.051(2) -0.0042(19) -0.0007(17) -0.0107(17) O18 0.0216(10) 0.0286(11) 0.0214(10) 0.0015(9) 0.0039(8) -0.0001(9) C19 0.0233(15) 0.043(2) 0.0408(19) 0.0059(16) 0.0100(14) -0.0029(15) C20 0.043(2) 0.064(3) 0.053(2) -0.015(2) 0.0145(18) -0.024(2) C21 0.044(2) 0.074(3) 0.046(2) -0.008(2) 0.0256(18) -0.007(2) C22 0.0401(19) 0.038(2) 0.040(2) 0.0031(16) 0.0111(16) 0.0018(16) C23 0.049(2) 0.047(2) 0.040(2) -0.0079(17) 0.0166(17) 0.0019(18) C24 0.0354(18) 0.0369(19) 0.0384(19) -0.0044(16) 0.0074(15) 0.0022(15) C25 0.0312(16) 0.0292(17) 0.0409(19) -0.0031(15) 0.0131(14) 0.0060(14) C26 0.0333(18) 0.041(2) 0.048(2) -0.0106(17) 0.0099(16) 0.0012(16) C27 0.0327(18) 0.046(2) 0.053(2) -0.0097(19) 0.0130(17) 0.0001(17) N28 0.0306(14) 0.0340(15) 0.0363(15) -0.0006(12) 0.0100(12) 0.0053(12) C29 0.0270(15) 0.0291(17) 0.0358(18) -0.0024(14) 0.0078(14) -0.0041(14) S30 0.0299(4) 0.0453(5) 0.0491(5) 0.0162(4) 0.0147(4) 0.0074(4) N31 0.0280(14) 0.0389(16) 0.0378(16) -0.0011(13) 0.0095(12) 0.0040(13) P32 0.0380(5) 0.0562(6) 0.0297(5) 0.0020(4) 0.0061(4) 0.0026(5) S33 0.0502(6) 0.0709(7) 0.0385(5) 0.0104(5) 0.0058(4) 0.0194(5) O34 0.067(2) 0.091(3) 0.0470(17) -0.0087(17) 0.0147(15) 0.0105(19) C35 0.091(4) 0.064(3) 0.075(4) -0.009(3) 0.012(3) -0.010(3) C36 0.080(4) 0.092(4) 0.051(3) -0.009(3) 0.006(3) 0.004(3) C37 0.202(9) 0.114(6) 0.151(8) -0.051(6) -0.071(7) 0.076(6) O38 0.0551(18) 0.083(2) 0.066(2) 0.0162(17) 0.0130(16) -0.0159(17) C39 0.086(7) 0.074(7) 0.071(6) 0.021(5) 0.016(5) -0.013(5) C40 0.32(2) 0.126(12) 0.119(9) 0.006(8) 0.124(11) -0.079(13) C41 0.067(6) 0.079(7) 0.143(10) 0.020(7) 0.026(7) -0.016(5) C51 0.065(5) 0.051(5) 0.095(8) -0.006(5) 0.024(5) -0.008(5) C52 0.057(5) 0.052(6) 0.132(11) -0.006(6) 0.002(6) 0.010(4) C53 0.045(6) 0.066(6) 0.25(2) -0.007(9) -0.018(9) -0.001(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 C22 1.510(5) . ? C1 C2 1.522(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C7 1.517(5) . ? C2 C3 1.542(5) . ? C2 H2 1.0000 . ? C3 C4 1.526(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.514(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N8 1.461(4) . ? C5 C6 1.521(4) . ? C5 H5 1.0000 . ? C6 C7 1.520(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C9 1.331(4) . ? N8 H8 0.8800 . ? C9 N11 1.384(4) . ? C9 S10 1.672(3) . ? N11 P12 1.671(2) . ? N11 H11 0.8800 . ? P12 O18 1.567(2) . ? P12 O14 1.584(2) . ? P12 S13 1.9103(11) . ? O14 C15 1.470(4) . ? C15 C17 1.497(5) . ? C15 C16 1.505(5) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O18 C19 1.478(4) . ? C19 C21 1.493(5) . ? C19 C20 1.504(5) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C27 1.512(5) . ? C22 C23 1.548(5) . ? C22 H22 1.0000 . ? C23 C24 1.522(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.515(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N28 1.453(5) . ? C25 C26 1.534(5) . ? C25 H25 1.0000 . ? C26 C27 1.504(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? N28 C29 1.320(4) . ? N28 H28 0.8800 . ? C29 N31 1.389(5) . ? C29 S30 1.680(3) . ? N31 P32 1.662(3) . ? N31 H31 0.8800 . ? P32 O34 1.541(3) . ? P32 O38 1.567(3) . ? P32 S33 1.9172(15) . ? O34 C35 1.437(6) . ? C35 C36 1.471(7) . ? C35 C37 1.505(9) . ? C35 H35 1.0000 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? O38 C39 1.341(11) . ? O38 C51 1.557(11) . ? C39 C41 1.485(16) . ? C39 C40 1.490(19) . ? C39 H39 1.0000 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C51 C52 1.457(14) . ? C51 C53 1.508(16) . ? C51 H51 1.0000 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? 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 C22 C1 C2 117.0(3) . . ? C22 C1 H1A 108.0 . . ? C2 C1 H1A 108.0 . . ? C22 C1 H1B 108.0 . . ? C2 C1 H1B 108.0 . . ? H1A C1 H1B 107.3 . . ? C7 C2 C1 109.5(3) . . ? C7 C2 C3 110.3(3) . . ? C1 C2 C3 111.9(3) . . ? C7 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C4 C3 C2 113.0(3) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 109.9(3) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N8 C5 C4 110.6(3) . . ? N8 C5 C6 110.7(3) . . ? C4 C5 C6 111.0(3) . . ? N8 C5 H5 108.2 . . ? C4 C5 H5 108.2 . . ? C6 C5 H5 108.2 . . ? C7 C6 C5 109.6(3) . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C2 C7 C6 112.3(3) . . ? C2 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C2 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C9 N8 C5 124.2(2) . . ? C9 N8 H8 117.9 . . ? C5 N8 H8 117.9 . . ? N8 C9 N11 117.1(3) . . ? N8 C9 S10 123.4(2) . . ? N11 C9 S10 119.5(2) . . ? C9 N11 P12 129.7(2) . . ? C9 N11 H11 115.1 . . ? P12 N11 H11 115.1 . . ? O18 P12 O14 95.23(11) . . ? O18 P12 N11 106.07(12) . . ? O14 P12 N11 106.27(12) . . ? O18 P12 S13 119.27(9) . . ? O14 P12 S13 118.13(9) . . ? N11 P12 S13 110.17(10) . . ? C15 O14 P12 122.04(19) . . ? O14 C15 C17 107.3(3) . . ? O14 C15 C16 106.1(3) . . ? C17 C15 C16 113.9(3) . . ? O14 C15 H15 109.8 . . ? C17 C15 H15 109.8 . . ? C16 C15 H15 109.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 O18 P12 119.6(2) . . ? O18 C19 C21 107.5(3) . . ? O18 C19 C20 106.7(3) . . ? C21 C19 C20 113.6(3) . . ? O18 C19 H19 109.7 . . ? C21 C19 H19 109.7 . . ? C20 C19 H19 109.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 C22 C27 110.6(3) . . ? C1 C22 C23 113.3(3) . . ? C27 C22 C23 108.7(3) . . ? C1 C22 H22 108.0 . . ? C27 C22 H22 108.0 . . ? C23 C22 H22 108.0 . . ? C24 C23 C22 111.8(3) . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 111.0(3) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? N28 C25 C24 112.0(3) . . ? N28 C25 C26 106.6(3) . . ? C24 C25 C26 111.2(3) . . ? N28 C25 H25 109.0 . . ? C24 C25 H25 109.0 . . ? C26 C25 H25 109.0 . . ? C27 C26 C25 111.8(3) . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? C26 C27 C22 111.6(3) . . ? C26 C27 H27A 109.3 . . ? C22 C27 H27A 109.3 . . ? C26 C27 H27B 109.3 . . ? C22 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C29 N28 C25 127.2(3) . . ? C29 N28 H28 116.4 . . ? C25 N28 H28 116.4 . . ? N28 C29 N31 117.6(3) . . ? N28 C29 S30 123.5(3) . . ? N31 C29 S30 118.9(2) . . ? C29 N31 P32 134.8(2) . . ? C29 N31 H31 112.6 . . ? P32 N31 H31 112.6 . . ? O34 P32 O38 97.3(2) . . ? O34 P32 N31 105.98(18) . . ? O38 P32 N31 103.53(16) . . ? O34 P32 S33 116.14(14) . . ? O38 P32 S33 115.92(15) . . ? N31 P32 S33 115.69(12) . . ? C35 O34 P32 121.9(4) . . ? O34 C35 C36 111.8(5) . . ? O34 C35 C37 108.2(5) . . ? C36 C35 C37 111.8(6) . . ? O34 C35 H35 108.3 . . ? C36 C35 H35 108.3 . . ? C37 C35 H35 108.3 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 O38 C51 80.3(7) . . ? C39 O38 P32 125.9(5) . . ? C51 O38 P32 121.3(5) . . ? O38 C39 C41 107.0(9) . . ? O38 C39 C40 114.0(11) . . ? C41 C39 C40 104.9(12) . . ? O38 C39 H39 110.2 . . ? C41 C39 H39 110.2 . . ? C40 C39 H39 110.2 . . ? C52 C51 C53 112.3(9) . . ? C52 C51 O38 103.6(9) . . ? C53 C51 O38 113.5(10) . . ? C52 C51 H51 109.1 . . ? C53 C51 H51 109.1 . . ? O38 C51 H51 109.1 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 C1 C2 C7 176.7(3) . . . . ? C22 C1 C2 C3 -60.7(4) . . . . ? C7 C2 C3 C4 -52.0(4) . . . . ? C1 C2 C3 C4 -174.1(3) . . . . ? C2 C3 C4 C5 54.3(4) . . . . ? C3 C4 C5 N8 178.8(3) . . . . ? C3 C4 C5 C6 -58.0(4) . . . . ? N8 C5 C6 C7 -177.0(3) . . . . ? C4 C5 C6 C7 59.8(4) . . . . ? C1 C2 C7 C6 177.1(3) . . . . ? C3 C2 C7 C6 53.6(4) . . . . ? C5 C6 C7 C2 -57.9(4) . . . . ? C4 C5 N8 C9 -95.3(4) . . . . ? C6 C5 N8 C9 141.3(3) . . . . ? C5 N8 C9 N11 178.9(3) . . . . ? C5 N8 C9 S10 -0.6(5) . . . . ? N8 C9 N11 P12 10.7(4) . . . . ? S10 C9 N11 P12 -169.72(18) . . . . ? C9 N11 P12 O18 52.2(3) . . . . ? C9 N11 P12 O14 -48.3(3) . . . . ? C9 N11 P12 S13 -177.4(3) . . . . ? O18 P12 O14 C15 164.5(2) . . . . ? N11 P12 O14 C15 -87.0(2) . . . . ? S13 P12 O14 C15 37.2(2) . . . . ? P12 O14 C15 C17 -107.9(3) . . . . ? P12 O14 C15 C16 130.0(3) . . . . ? O14 P12 O18 C19 172.5(2) . . . . ? N11 P12 O18 C19 63.8(2) . . . . ? S13 P12 O18 C19 -61.1(2) . . . . ? P12 O18 C19 C21 117.8(3) . . . . ? P12 O18 C19 C20 -120.0(3) . . . . ? C2 C1 C22 C27 169.6(3) . . . . ? C2 C1 C22 C23 -68.0(4) . . . . ? C1 C22 C23 C24 179.4(3) . . . . ? C27 C22 C23 C24 -57.2(4) . . . . ? C22 C23 C24 C25 55.9(4) . . . . ? C23 C24 C25 N28 -172.6(3) . . . . ? C23 C24 C25 C26 -53.4(4) . . . . ? N28 C25 C26 C27 176.7(3) . . . . ? C24 C25 C26 C27 54.3(4) . . . . ? C25 C26 C27 C22 -57.2(4) . . . . ? C1 C22 C27 C26 -177.4(3) . . . . ? C23 C22 C27 C26 57.6(4) . . . . ? C24 C25 N28 C29 -84.8(4) . . . . ? C26 C25 N28 C29 153.4(3) . . . . ? C25 N28 C29 N31 179.9(3) . . . . ? C25 N28 C29 S30 -1.5(5) . . . . ? N28 C29 N31 P32 -6.6(5) . . . . ? S30 C29 N31 P32 174.8(2) . . . . ? C29 N31 P32 O34 140.9(3) . . . . ? C29 N31 P32 O38 -117.3(4) . . . . ? C29 N31 P32 S33 10.7(4) . . . . ? O38 P32 O34 C35 174.5(4) . . . . ? N31 P32 O34 C35 -79.1(4) . . . . ? S33 P32 O34 C35 50.9(4) . . . . ? P32 O34 C35 C36 -103.6(5) . . . . ? P32 O34 C35 C37 132.9(6) . . . . ? O34 P32 O38 C39 -76.7(8) . . . . ? N31 P32 O38 C39 174.9(7) . . . . ? S33 P32 O38 C39 47.1(8) . . . . ? O34 P32 O38 C51 -178.0(5) . . . . ? N31 P32 O38 C51 73.6(5) . . . . ? S33 P32 O38 C51 -54.2(5) . . . . ? C51 O38 C39 C41 -45.0(10) . . . . ? P32 O38 C39 C41 -166.8(7) . . . . ? C51 O38 C39 C40 -160.6(13) . . . . ? P32 O38 C39 C40 77.6(14) . . . . ? C39 O38 C51 C52 84.5(10) . . . . ? P32 O38 C51 C52 -149.2(7) . . . . ? C39 O38 C51 C53 -37.5(11) . . . . ? P32 O38 C51 C53 88.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.126 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.089 # Attachment '- diamine.cif' data_saf72 _database_code_depnum_ccdc_archive 'CCDC 844834' #TrackingRef '- diamine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H12 N2 O2 S), C H2 Cl2' _chemical_formula_sum 'C25 H26 Cl2 N4 O4 S2' _chemical_formula_weight 581.52 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' 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/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 8.307(3) _cell_length_b 16.535(6) _cell_length_c 20.361(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.04(2) _cell_angle_gamma 90.00 _cell_volume 2700.9(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3492 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 36.76 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.434 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8240 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2009)' _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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37402 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 31.00 _reflns_number_total 8467 _reflns_number_gt 6424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1002P)^2^+0.5624P] 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 8467 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1525 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 S1 S 0.55788(5) 0.86512(3) 0.87390(2) 0.01786(11) Uani 1 1 d . . . O1 O 0.46383(17) 0.83955(8) 0.92156(8) 0.0253(3) Uani 1 1 d . . . O2 O 0.54782(17) 0.81489(9) 0.81505(8) 0.0264(3) Uani 1 1 d . . . N1 N 0.3525(2) 1.19565(10) 0.77862(10) 0.0287(4) Uani 1 1 d . . . H1B H 0.2900 1.2236 0.7977 0.034 Uiso 1 1 calc R . . H1C H 0.3853 1.2158 0.7454 0.034 Uiso 1 1 calc R . . N2 N 1.2678(2) 0.89978(11) 1.02170(10) 0.0283(4) Uani 1 1 d . . . H2B H 1.3435 0.8936 1.0002 0.034 Uiso 1 1 calc R . . H2C H 1.2954 0.9119 1.0642 0.034 Uiso 1 1 calc R . . C1 C 0.4916(2) 0.96227(11) 0.84532(9) 0.0175(3) Uani 1 1 d . . . C2 C 0.5445(3) 0.99500(12) 0.79090(10) 0.0249(4) Uani 1 1 d . . . H2A H 0.6098 0.9643 0.7695 0.030 Uiso 1 1 calc R . . C3 C 0.4997(3) 1.07258(13) 0.76911(10) 0.0264(4) Uani 1 1 d . . . H3A H 0.5357 1.0941 0.7332 0.032 Uiso 1 1 calc R . . C4 C 0.3993(2) 1.11997(11) 0.80090(10) 0.0203(3) Uani 1 1 d . . . C5 C 0.3473(2) 1.08590(11) 0.85504(9) 0.0189(3) Uani 1 1 d . . . H5A H 0.2806 1.1160 0.8762 0.023 Uiso 1 1 calc R . . C6 C 0.3934(2) 1.00862(11) 0.87732(9) 0.0181(3) Uani 1 1 d . . . H6A H 0.3592 0.9872 0.9137 0.022 Uiso 1 1 calc R . . C7 C 0.7676(2) 0.87351(11) 0.91837(9) 0.0178(3) Uani 1 1 d . . . C8 C 0.8910(2) 0.86249(12) 0.88373(10) 0.0206(3) Uani 1 1 d . . . H8A H 0.8616 0.8498 0.8377 0.025 Uiso 1 1 calc R . . C9 C 1.0573(2) 0.87065(12) 0.91856(10) 0.0232(4) Uani 1 1 d . . . H9A H 1.1395 0.8630 0.8957 0.028 Uiso 1 1 calc R . . C10 C 1.1029(2) 0.89035(11) 0.98804(11) 0.0230(4) Uani 1 1 d . . . C11 C 0.9761(2) 0.90188(13) 1.02185(10) 0.0265(4) Uani 1 1 d . . . H11A H 1.0044 0.9151 1.0678 0.032 Uiso 1 1 calc R . . C12 C 0.8108(2) 0.89375(12) 0.98718(10) 0.0230(4) Uani 1 1 d . . . H12A H 0.7280 0.9018 1.0097 0.028 Uiso 1 1 calc R . . S2 S -0.05481(6) 0.84846(3) 0.67579(2) 0.02115(11) Uani 1 1 d . . . O3 O -0.20137(17) 0.80407(9) 0.63803(8) 0.0274(3) Uani 1 1 d . . . O4 O 0.01934(19) 0.82527(9) 0.74547(7) 0.0281(3) Uani 1 1 d . . . N3 N 0.4672(2) 0.80309(12) 0.52928(10) 0.0322(4) Uani 1 1 d . . . H3B H 0.5702 0.8098 0.5505 0.039 Uiso 1 1 calc R . . H3C H 0.4407 0.7889 0.4872 0.039 Uiso 1 1 calc R . . N4 N -0.2318(3) 1.19493(11) 0.67118(11) 0.0362(4) Uani 1 1 d . . . H4B H -0.3201 1.2124 0.6425 0.043 Uiso 1 1 calc R . . H4C H -0.1683 1.2280 0.6988 0.043 Uiso 1 1 calc R . . C13 C 0.0975(2) 0.83828(11) 0.63107(9) 0.0198(3) Uani 1 1 d . . . C14 C 0.0526(2) 0.81726(12) 0.56241(10) 0.0234(4) Uani 1 1 d . . . H14A H -0.0592 0.8110 0.5395 0.028 Uiso 1 1 calc R . . C15 C 0.1754(3) 0.80571(12) 0.52846(10) 0.0257(4) Uani 1 1 d . . . H15A H 0.1456 0.7916 0.4827 0.031 Uiso 1 1 calc R . . C16 C 0.3448(2) 0.81510(12) 0.56256(11) 0.0242(4) Uani 1 1 d . . . C17 C 0.3870(2) 0.83831(12) 0.63122(10) 0.0247(4) Uani 1 1 d . . . H17A H 0.4983 0.8463 0.6540 0.030 Uiso 1 1 calc R . . C18 C 0.2648(2) 0.84947(12) 0.66529(10) 0.0234(4) Uani 1 1 d . . . H18A H 0.2939 0.8644 0.7109 0.028 Uiso 1 1 calc R . . C19 C -0.1112(2) 0.95052(11) 0.67595(10) 0.0208(3) Uani 1 1 d . . . C20 C -0.2545(2) 0.97927(12) 0.62949(10) 0.0243(4) Uani 1 1 d . . . H20A H -0.3229 0.9437 0.5993 0.029 Uiso 1 1 calc R . . C21 C -0.2949(3) 1.06034(12) 0.62822(11) 0.0265(4) Uani 1 1 d . . . H21A H -0.3911 1.0789 0.5974 0.032 Uiso 1 1 calc R . . C22 C -0.1927(2) 1.11495(12) 0.67282(11) 0.0252(4) Uani 1 1 d . . . C23 C -0.0500(3) 1.08516(13) 0.72019(11) 0.0285(4) Uani 1 1 d . . . H23A H 0.0179 1.1207 0.7506 0.034 Uiso 1 1 calc R . . C24 C -0.0092(2) 1.00394(13) 0.72228(11) 0.0260(4) Uani 1 1 d . . . H24A H 0.0848 0.9849 0.7540 0.031 Uiso 1 1 calc R . . Cl1 Cl 0.75928(9) 0.51815(4) 0.97406(3) 0.04343(16) Uani 1 1 d . . . Cl2 Cl 0.76622(10) 0.66079(4) 0.89244(3) 0.04987(19) Uani 1 1 d . . . C25 C 0.8238(4) 0.55858(16) 0.90546(13) 0.0414(6) Uani 1 1 d . . . H25A H 0.7737 0.5280 0.8646 0.050 Uiso 1 1 calc R . . H25B H 0.9439 0.5538 0.9144 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01529(19) 0.0150(2) 0.0235(2) -0.00032(15) 0.00553(15) 0.00101(14) O1 0.0187(6) 0.0223(7) 0.0375(8) 0.0088(6) 0.0122(6) 0.0021(5) O2 0.0244(7) 0.0209(7) 0.0307(7) -0.0096(6) 0.0012(6) 0.0025(5) N1 0.0375(9) 0.0196(8) 0.0345(9) 0.0067(7) 0.0192(8) 0.0050(7) N2 0.0170(7) 0.0317(9) 0.0323(9) -0.0024(7) -0.0008(6) -0.0005(6) C1 0.0171(7) 0.0169(8) 0.0191(8) 0.0003(6) 0.0056(6) 0.0010(6) C2 0.0284(9) 0.0252(9) 0.0261(9) 0.0025(7) 0.0159(8) 0.0059(7) C3 0.0316(10) 0.0263(10) 0.0271(10) 0.0059(8) 0.0180(8) 0.0049(8) C4 0.0203(8) 0.0181(8) 0.0232(9) 0.0007(7) 0.0070(7) 0.0011(6) C5 0.0191(8) 0.0193(8) 0.0201(8) -0.0006(6) 0.0080(6) 0.0029(6) C6 0.0171(7) 0.0193(8) 0.0190(8) 0.0000(6) 0.0065(6) 0.0010(6) C7 0.0150(7) 0.0176(8) 0.0214(8) -0.0004(6) 0.0060(6) 0.0021(6) C8 0.0185(8) 0.0239(9) 0.0206(8) -0.0023(7) 0.0073(6) 0.0006(7) C9 0.0173(8) 0.0248(9) 0.0297(10) -0.0017(7) 0.0100(7) 0.0007(7) C10 0.0182(8) 0.0195(9) 0.0290(10) -0.0001(7) 0.0019(7) 0.0000(6) C11 0.0251(9) 0.0304(10) 0.0219(9) -0.0028(8) 0.0019(7) 0.0040(8) C12 0.0212(8) 0.0274(10) 0.0219(9) -0.0004(7) 0.0081(7) 0.0045(7) S2 0.0210(2) 0.0185(2) 0.0257(2) 0.00196(16) 0.00923(17) -0.00052(16) O3 0.0219(6) 0.0213(7) 0.0401(8) -0.0007(6) 0.0103(6) -0.0052(5) O4 0.0344(8) 0.0277(7) 0.0251(7) 0.0070(6) 0.0129(6) 0.0062(6) N3 0.0303(9) 0.0364(10) 0.0340(10) -0.0083(8) 0.0160(8) -0.0025(7) N4 0.0355(10) 0.0203(9) 0.0485(12) -0.0048(8) 0.0035(9) 0.0029(7) C13 0.0195(8) 0.0184(8) 0.0225(9) -0.0007(7) 0.0071(6) 0.0000(6) C14 0.0224(8) 0.0206(9) 0.0261(9) -0.0013(7) 0.0043(7) -0.0039(7) C15 0.0307(10) 0.0237(9) 0.0232(9) -0.0057(7) 0.0081(8) -0.0047(8) C16 0.0264(9) 0.0189(8) 0.0298(10) -0.0031(7) 0.0116(8) -0.0013(7) C17 0.0194(8) 0.0264(10) 0.0285(10) -0.0022(8) 0.0065(7) 0.0007(7) C18 0.0207(8) 0.0263(9) 0.0230(9) -0.0026(7) 0.0053(7) 0.0003(7) C19 0.0195(8) 0.0191(8) 0.0259(9) 0.0001(7) 0.0097(7) 0.0001(6) C20 0.0229(9) 0.0231(9) 0.0261(9) -0.0005(7) 0.0050(7) -0.0019(7) C21 0.0239(9) 0.0239(9) 0.0296(10) 0.0016(8) 0.0031(7) 0.0018(7) C22 0.0247(9) 0.0215(9) 0.0312(10) -0.0010(7) 0.0103(8) 0.0002(7) C23 0.0254(9) 0.0259(10) 0.0327(11) -0.0078(8) 0.0046(8) -0.0018(8) C24 0.0213(8) 0.0268(10) 0.0281(10) -0.0029(8) 0.0030(7) 0.0017(7) Cl1 0.0565(4) 0.0339(3) 0.0415(3) 0.0069(2) 0.0155(3) 0.0029(3) Cl2 0.0720(5) 0.0298(3) 0.0393(3) 0.0077(2) -0.0009(3) 0.0040(3) C25 0.0564(15) 0.0341(12) 0.0367(12) 0.0050(10) 0.0172(11) 0.0130(11) _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 O2 1.4424(15) . ? S1 O1 1.4574(15) . ? S1 C7 1.7480(19) . ? S1 C1 1.7482(19) . ? N1 C4 1.353(2) . ? N1 H1B 0.8600 . ? N1 H1C 0.8600 . ? N2 C10 1.372(2) . ? N2 H2B 0.8600 . ? N2 H2C 0.8600 . ? C1 C6 1.397(2) . ? C1 C2 1.402(3) . ? C2 C3 1.377(3) . ? C2 H2A 0.9300 . ? C3 C4 1.417(3) . ? C3 H3A 0.9300 . ? C4 C5 1.402(3) . ? C5 C6 1.377(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C12 1.394(3) . ? C7 C8 1.399(2) . ? C8 C9 1.386(3) . ? C8 H8A 0.9300 . ? C9 C10 1.404(3) . ? C9 H9A 0.9300 . ? C10 C11 1.412(3) . ? C11 C12 1.378(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? S2 O4 1.4442(16) . ? S2 O3 1.4581(15) . ? S2 C13 1.7484(19) . ? S2 C19 1.752(2) . ? N3 C16 1.375(3) . ? N3 H3B 0.8600 . ? N3 H3C 0.8600 . ? N4 C22 1.360(3) . ? N4 H4B 0.8600 . ? N4 H4C 0.8600 . ? C13 C14 1.394(3) . ? C13 C18 1.395(3) . ? C14 C15 1.386(3) . ? C14 H14A 0.9300 . ? C15 C16 1.406(3) . ? C15 H15A 0.9300 . ? C16 C17 1.404(3) . ? C17 C18 1.383(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C20 1.398(3) . ? C19 C24 1.405(3) . ? C20 C21 1.380(3) . ? C20 H20A 0.9300 . ? C21 C22 1.400(3) . ? C21 H21A 0.9300 . ? C22 C23 1.409(3) . ? C23 C24 1.383(3) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? Cl1 C25 1.753(3) . ? Cl2 C25 1.758(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? 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 O2 S1 O1 117.42(9) . . ? O2 S1 C7 108.13(9) . . ? O1 S1 C7 108.21(9) . . ? O2 S1 C1 107.89(9) . . ? O1 S1 C1 108.14(8) . . ? C7 S1 C1 106.55(9) . . ? C4 N1 H1B 120.0 . . ? C4 N1 H1C 120.0 . . ? H1B N1 H1C 120.0 . . ? C10 N2 H2B 120.0 . . ? C10 N2 H2C 120.0 . . ? H2B N2 H2C 120.0 . . ? C6 C1 C2 119.81(17) . . ? C6 C1 S1 121.34(14) . . ? C2 C1 S1 118.80(13) . . ? C3 C2 C1 120.04(17) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 120.65(17) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? N1 C4 C5 121.00(17) . . ? N1 C4 C3 120.66(17) . . ? C5 C4 C3 118.33(17) . . ? C6 C5 C4 121.06(16) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C5 C6 C1 120.11(16) . . ? C5 C6 H6A 119.9 . . ? C1 C6 H6A 119.9 . . ? C12 C7 C8 120.45(17) . . ? C12 C7 S1 120.13(13) . . ? C8 C7 S1 119.38(14) . . ? C9 C8 C7 119.52(17) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C8 C9 C10 120.69(17) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? N2 C10 C9 120.18(18) . . ? N2 C10 C11 121.00(19) . . ? C9 C10 C11 118.81(17) . . ? C12 C11 C10 120.46(18) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C7 120.06(17) . . ? C11 C12 H12A 120.0 . . ? C7 C12 H12A 120.0 . . ? O4 S2 O3 117.98(9) . . ? O4 S2 C13 107.71(9) . . ? O3 S2 C13 107.16(9) . . ? O4 S2 C19 107.46(9) . . ? O3 S2 C19 107.38(9) . . ? C13 S2 C19 108.90(9) . . ? C16 N3 H3B 120.0 . . ? C16 N3 H3C 120.0 . . ? H3B N3 H3C 120.0 . . ? C22 N4 H4B 120.0 . . ? C22 N4 H4C 120.0 . . ? H4B N4 H4C 120.0 . . ? C14 C13 C18 120.45(17) . . ? C14 C13 S2 120.29(14) . . ? C18 C13 S2 119.24(15) . . ? C15 C14 C13 119.60(18) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 120.66(18) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? N3 C16 C17 120.31(19) . . ? N3 C16 C15 120.90(19) . . ? C17 C16 C15 118.77(18) . . ? C18 C17 C16 120.66(18) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C17 C18 C13 119.82(18) . . ? C17 C18 H18A 120.1 . . ? C13 C18 H18A 120.1 . . ? C20 C19 C24 120.02(18) . . ? C20 C19 S2 120.51(15) . . ? C24 C19 S2 119.46(15) . . ? C21 C20 C19 120.21(18) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C20 C21 C22 120.70(19) . . ? C20 C21 H21A 119.6 . . ? C22 C21 H21A 119.6 . . ? N4 C22 C21 120.7(2) . . ? N4 C22 C23 120.66(19) . . ? C21 C22 C23 118.65(19) . . ? C24 C23 C22 121.10(19) . . ? C24 C23 H23A 119.5 . . ? C22 C23 H23A 119.5 . . ? C23 C24 C19 119.30(19) . . ? C23 C24 H24A 120.3 . . ? C19 C24 H24A 120.3 . . ? Cl1 C25 Cl2 111.05(14) . . ? Cl1 C25 H25A 109.4 . . ? Cl2 C25 H25A 109.4 . . ? Cl1 C25 H25B 109.4 . . ? Cl2 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 C1 C6 140.63(15) . . . . ? O1 S1 C1 C6 12.67(18) . . . . ? C7 S1 C1 C6 -103.46(16) . . . . ? O2 S1 C1 C2 -42.00(18) . . . . ? O1 S1 C1 C2 -169.95(15) . . . . ? C7 S1 C1 C2 73.92(17) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? S1 C1 C2 C3 -177.40(16) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 N1 -178.7(2) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? N1 C4 C5 C6 179.35(18) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? S1 C1 C6 C5 178.00(14) . . . . ? O2 S1 C7 C12 -157.85(15) . . . . ? O1 S1 C7 C12 -29.69(18) . . . . ? C1 S1 C7 C12 86.39(17) . . . . ? O2 S1 C7 C8 24.34(18) . . . . ? O1 S1 C7 C8 152.50(15) . . . . ? C1 S1 C7 C8 -91.42(16) . . . . ? C12 C7 C8 C9 1.0(3) . . . . ? S1 C7 C8 C9 178.77(15) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 N2 -178.76(19) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? N2 C10 C11 C12 178.76(19) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C8 C7 C12 C11 -1.0(3) . . . . ? S1 C7 C12 C11 -178.74(16) . . . . ? O4 S2 C13 C14 148.38(16) . . . . ? O3 S2 C13 C14 20.49(18) . . . . ? C19 S2 C13 C14 -95.37(17) . . . . ? O4 S2 C13 C18 -30.05(18) . . . . ? O3 S2 C13 C18 -157.94(15) . . . . ? C19 S2 C13 C18 86.20(17) . . . . ? C18 C13 C14 C15 1.4(3) . . . . ? S2 C13 C14 C15 -176.99(15) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 N3 179.47(19) . . . . ? C14 C15 C16 C17 -1.5(3) . . . . ? N3 C16 C17 C18 -179.14(19) . . . . ? C15 C16 C17 C18 1.8(3) . . . . ? C16 C17 C18 C13 -0.6(3) . . . . ? C14 C13 C18 C17 -1.1(3) . . . . ? S2 C13 C18 C17 177.32(15) . . . . ? O4 S2 C19 C20 -145.10(16) . . . . ? O3 S2 C19 C20 -17.22(18) . . . . ? C13 S2 C19 C20 98.50(17) . . . . ? O4 S2 C19 C24 36.28(18) . . . . ? O3 S2 C19 C24 164.15(15) . . . . ? C13 S2 C19 C24 -80.13(18) . . . . ? C24 C19 C20 C21 1.0(3) . . . . ? S2 C19 C20 C21 -177.60(16) . . . . ? C19 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 N4 179.5(2) . . . . ? C20 C21 C22 C23 -1.6(3) . . . . ? N4 C22 C23 C24 180.0(2) . . . . ? C21 C22 C23 C24 1.0(3) . . . . ? C22 C23 C24 C19 0.5(3) . . . . ? C20 C19 C24 C23 -1.6(3) . . . . ? S2 C19 C24 C23 177.07(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B O3 0.86 2.13 2.962(2) 163.9 2_556 N4 H4B O1 0.86 2.60 3.333(3) 144.4 2_556 N4 H4C O4 0.86 2.16 3.014(3) 170.6 2_556 N1 H1C O2 0.86 2.20 3.005(2) 154.7 2_656 N2 H2B O1 0.86 2.28 3.086(3) 156.3 1_655 N3 H3B O3 0.86 2.24 3.053(3) 157.0 1_655 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.813 _refine_diff_density_min -0.776 _refine_diff_density_rms 0.108