# Supplementary Material (ESI) for Medicinal Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full MedChemComm _journal_coden_Cambridge 1476 _publ_contact_author_name 'Palmer, R.' _publ_contact_author_email rex.palmer@btinternet.com _publ_section_title ; An Absolute Structure Template for a Unique Voltage-Gated Sodium Channel Binding Site ; loop_ _publ_author_name R.Palmer B.Potter M.Leach T.Jenkins B.Chowdhry data_BW202W92P1(SpaceGroupP21) _database_code_depnum_ccdc_archive 'CCDC 299482' _journal_full_name ; Medicinal Chemistry Communications _audit_creation_method SHELXL-97 _chemical_name_systematic 'R-2,4-diamino-6-(fluoromethyl)-5- (2,3,5-trichlorophenyl)pyrimidine' ; _chemical_name_common 'BW202W92 R-enantiomer' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C11 H9 Cl3 F N4 C H3 S O3' _chemical_formula_sum 'C12 H12 Cl3 F N4 O3 S' _chemical_formula_weight 417.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.384(2) _cell_length_b 16.984(3) _cell_length_c 12.480(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.14(2) _cell_angle_gamma 90.00 _cell_volume 1723.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25 _cell_measurement_theta_max 28 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 6.238 _exptl_absorpt_correction_type 'empirical via \psi scans' _exptl_absorpt_process_details '(North, Philips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.3532 _exptl_absorpt_correction_T_max 0.5678 _exptl_special_details ; Room temperature on glass fibre ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method \w-/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 97 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3990 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 74.42 _reflns_number_total 3192 _reflns_number_gt 2581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_cell_refinement 'SET4 and CELDIM in CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_data_reduction ; CCP4: CAD77, CADRAL, CADSHEL The HKL Manual, 4th edition in Sawyer et al., 1993: "Data Collection and Processing": Proceedings of the CCP4 Study Weekend 29-30 January 1993 (Eds. L.Sawyer, N.Isaacs and S.Bailey) SERC Daresbury Laboratory* DL/SC1/R34. ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1998)' _computing_publication_material SHELX97 _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^)+(0.0826P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00153(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 3192 _refine_ls_number_parameters 483 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.005 _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 C1A C 0.4829(7) -0.1549(3) 0.9073(4) 0.0406(14) Uani 1 1 d . . . C2A C 0.4048(7) -0.1073(3) 0.9718(5) 0.0469(15) Uani 1 1 d . . . Cl2A Cl 0.29324(19) -0.02552(8) 0.91380(11) 0.0589(4) Uani 1 1 d . . . C3A C 0.4186(7) -0.1248(3) 1.0822(4) 0.0506(16) Uani 1 1 d . . . Cl3A Cl 0.33606(19) -0.06436(9) 1.16533(11) 0.0591(4) Uani 1 1 d . . . C4A C 0.5052(6) -0.1908(3) 1.1302(4) 0.0419(14) Uani 1 1 d . . . H4A H 0.5156 -0.2024 1.2044 0.12(3) Uiso 1 1 calc R . . C5A C 0.5761(6) -0.2390(3) 1.0642(4) 0.0455(14) Uani 1 1 d . . . Cl5A Cl 0.6849(2) -0.32063(8) 1.12266(14) 0.0705(5) Uani 1 1 d . . . C6A C 0.5661(6) -0.2204(3) 0.9527(4) 0.0394(13) Uani 1 1 d . . . H6A H 0.6161 -0.2527 0.9103 0.070(18) Uiso 1 1 calc R . . C5'A C 0.4719(6) -0.1365(3) 0.7879(4) 0.0350(12) Uani 1 1 d . . . C6'A C 0.5558(6) -0.0757(3) 0.7558(3) 0.0376(13) Uani 1 1 d D . . C7'A C 0.6605(6) -0.0172(3) 0.8332(4) 0.0464(14) Uani 1 1 d . . . H71A H 0.6227 0.0359 0.8128 0.035(9) Uiso 1 1 calc R . . H72A H 0.6528 -0.0268 0.9084 0.035(9) Uiso 1 1 calc R . . F7'A F 0.8228(4) -0.0260(2) 0.8257(3) 0.0609(10) Uani 1 1 d . . . N1'A N 0.5534(5) -0.0657(2) 0.6477(3) 0.0449(12) Uani 1 1 d D . . C2'A C 0.4738(6) -0.1171(2) 0.5703(3) 0.0416(14) Uani 1 1 d D . . N2'A N 0.4873(6) -0.1110(2) 0.4678(3) 0.0527(14) Uani 1 1 d D . . N3'A N 0.3862(5) -0.1776(2) 0.5954(3) 0.0406(11) Uani 1 1 d . . . C4'A C 0.3834(5) -0.1867(2) 0.7017(3) 0.0338(12) Uani 1 1 d D . . N4'A N 0.2910(5) -0.2456(2) 0.7225(3) 0.0435(11) Uani 1 1 d D . . C1B C 0.9722(6) -0.1176(3) 0.4021(4) 0.0385(13) Uani 1 1 d . . . C2B C 1.0547(7) -0.0497(3) 0.4526(4) 0.0423(14) Uani 1 1 d . . . Cl2B Cl 1.14454(18) 0.01338(8) 0.37499(11) 0.0570(4) Uani 1 1 d . . . C3B C 1.0690(7) -0.0348(3) 0.5634(4) 0.0489(16) Uani 1 1 d . . . Cl3B Cl 1.1723(2) 0.04873(9) 0.62502(13) 0.0694(5) Uani 1 1 d . . . C4B C 1.0008(7) -0.0857(4) 0.6247(5) 0.0541(17) Uani 1 1 d . . . H4B H 1.0064 -0.0743 0.6984 0.024(11) Uiso 1 1 calc R . . C5B C 0.9257(7) -0.1520(3) 0.5794(4) 0.0440(15) Uani 1 1 d . . . Cl5B Cl 0.8459(2) -0.21710(10) 0.65936(13) 0.0705(5) Uani 1 1 d . . . C6B C 0.9091(6) -0.1683(3) 0.4681(4) 0.0394(13) Uani 1 1 d . . . H6B H 0.8550 -0.2139 0.4376 0.028(12) Uiso 1 1 calc R . . C5'B C 0.9671(7) -0.1360(3) 0.2864(5) 0.0413(14) Uani 1 1 d . . . C6'B C 1.0467(6) -0.1963(3) 0.2542(3) 0.0400(13) Uani 1 1 d D . . C7'B C 1.1523(7) -0.2556(3) 0.3282(4) 0.0452(15) Uani 1 1 d . . . H71B H 1.1433 -0.2488 0.4036 0.083(15) Uiso 1 1 calc R . . H72B H 1.1167 -0.3085 0.3045 0.083(15) Uiso 1 1 calc R . . F7'B F 1.3149(4) -0.24436(19) 0.3224(3) 0.0599(10) Uani 1 1 d . . . N1'B N 1.0434(5) -0.2069(2) 0.1445(3) 0.0410(11) Uani 1 1 d D . . C2'B C 0.9653(6) -0.1546(2) 0.0681(3) 0.0394(14) Uani 1 1 d D . . N2'B N 0.9741(6) -0.1665(2) -0.0362(3) 0.0503(13) Uani 1 1 d D . . N3'B N 0.8769(6) -0.0966(2) 0.0919(4) 0.0441(12) Uani 1 1 d . . . C4'B C 0.8713(6) -0.0863(3) 0.1979(4) 0.0410(14) Uani 1 1 d D . . N4'B N 0.7775(5) -0.0295(2) 0.2173(3) 0.0425(12) Uani 1 1 d D . . S1A S 0.68516(17) 0.08530(7) 0.47339(10) 0.0425(3) Uani 1 1 d . . . O1A O 0.6578(5) 0.0161(2) 0.4036(3) 0.0639(12) Uani 1 1 d . . . O2A O 0.7134(5) 0.0640(2) 0.5884(3) 0.0561(11) Uani 1 1 d . . . O3A O 0.8129(4) 0.1359(2) 0.4517(3) 0.0510(10) Uani 1 1 d . . . C8A C 1.0076(9) 0.0953(4) 0.0753(6) 0.078(2) Uiso 1 1 d . . . H8A1 H 1.0200 0.0790 0.1506 0.21(3) Uiso 1 1 calc R . . H8A2 H 1.0956 0.1304 0.0710 0.21(3) Uiso 1 1 calc R . . H8A3 H 1.0106 0.0500 0.0300 0.21(3) Uiso 1 1 calc R . . S1B S 0.81692(17) 0.14438(7) 0.02828(10) 0.0426(3) Uani 1 1 d . . . O1B O 0.8005(5) 0.1614(2) -0.0876(3) 0.0578(12) Uani 1 1 d . . . O2B O 0.8315(5) 0.2162(2) 0.0926(3) 0.0579(12) Uani 1 1 d . . . O3B O 0.6909(5) 0.0925(2) 0.0486(3) 0.0497(11) Uani 1 1 d . . . C8B C 0.5028(7) 0.1375(3) 0.4445(6) 0.0635(19) Uani 1 1 d . . . H8B1 H 0.4145 0.1032 0.4509 0.074(11) Uiso 1 1 calc R . . H8B2 H 0.4816 0.1580 0.3707 0.074(11) Uiso 1 1 calc R . . H8B3 H 0.5110 0.1802 0.4959 0.074(11) Uiso 1 1 calc R . . H21A H 0.5325(15) -0.0729(7) 0.4427(9) 0.060(18) Uiso 1 1 d D . . H22A H 0.449(3) -0.1437(7) 0.4167(7) 0.024(12) Uiso 1 1 d D . . H41A H 0.2376(16) -0.2763(6) 0.6731(11) 0.07(2) Uiso 1 1 d D . . H42A H 0.2761(18) -0.2549(11) 0.7861(8) 0.18(4) Uiso 1 1 d D . . H1'A H 0.6034(15) -0.0269(6) 0.6288(6) 0.08(2) Uiso 1 1 d D . . H21B H 0.994(2) -0.2109(6) -0.0574(9) 0.22(5) Uiso 1 1 d D . . H22B H 0.930(3) -0.1354(8) -0.0857(7) 0.07(2) Uiso 1 1 d D . . H41B H 0.7781(18) -0.0132(9) 0.2800(8) 0.027(12) Uiso 1 1 d D . . H42B H 0.7373(19) 0.0053(6) 0.1725(11) 0.023(12) Uiso 1 1 d D . . H1'B H 1.0949(15) -0.2445(6) 0.1272(6) 0.031(13) Uiso 1 1 d 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 C1A 0.058(3) 0.034(3) 0.030(2) 0.002(2) 0.011(2) -0.003(2) C2A 0.065(3) 0.031(2) 0.049(3) -0.001(2) 0.021(2) -0.001(3) Cl2A 0.0805(9) 0.0446(6) 0.0573(7) 0.0039(6) 0.0277(6) 0.0173(7) C3A 0.067(3) 0.052(3) 0.038(3) -0.009(2) 0.024(2) -0.006(3) Cl3A 0.0734(8) 0.0643(8) 0.0478(6) -0.0137(6) 0.0305(6) -0.0015(7) C4A 0.054(3) 0.037(2) 0.036(2) 0.005(2) 0.013(2) -0.003(2) C5A 0.045(3) 0.039(3) 0.053(3) 0.007(3) 0.012(2) 0.000(2) Cl5A 0.0866(11) 0.0498(8) 0.0709(10) 0.0202(7) 0.0111(9) 0.0113(8) C6A 0.045(3) 0.028(2) 0.048(3) 0.001(2) 0.016(2) 0.006(2) C5'A 0.048(3) 0.031(2) 0.029(2) -0.0006(19) 0.016(2) 0.001(2) C6'A 0.046(3) 0.032(2) 0.037(2) 0.003(2) 0.014(2) 0.002(2) C7'A 0.057(3) 0.039(3) 0.047(3) -0.011(2) 0.021(2) -0.017(3) F7'A 0.068(2) 0.0635(19) 0.0523(17) -0.0023(17) 0.0171(15) -0.0111(19) N1'A 0.063(3) 0.036(2) 0.038(2) -0.0047(19) 0.016(2) -0.010(2) C2'A 0.058(3) 0.034(2) 0.036(2) 0.008(2) 0.018(2) 0.005(2) N2'A 0.073(3) 0.049(3) 0.041(2) -0.005(2) 0.023(2) -0.014(2) N3'A 0.059(3) 0.033(2) 0.0326(19) -0.0037(17) 0.0176(18) -0.011(2) C4'A 0.045(3) 0.029(2) 0.032(2) -0.0076(19) 0.0176(18) -0.002(2) N4'A 0.056(2) 0.039(2) 0.041(2) -0.0045(19) 0.0230(18) -0.016(2) C1B 0.057(3) 0.029(2) 0.036(3) 0.002(2) 0.024(2) 0.005(2) C2B 0.050(3) 0.049(3) 0.026(2) -0.001(2) 0.006(2) 0.009(3) Cl2B 0.0680(8) 0.0528(7) 0.0514(7) -0.0004(6) 0.0166(6) -0.0163(7) C3B 0.058(3) 0.047(3) 0.040(3) -0.001(3) 0.007(2) 0.002(3) Cl3B 0.0885(12) 0.0648(9) 0.0499(8) -0.0173(7) 0.0074(8) -0.0077(9) C4B 0.049(3) 0.074(4) 0.047(3) 0.004(3) 0.026(2) 0.013(3) C5B 0.049(3) 0.046(3) 0.041(3) 0.006(2) 0.018(2) 0.004(3) Cl5B 0.0789(10) 0.0821(10) 0.0603(8) 0.0266(8) 0.0356(7) 0.0025(9) C6B 0.043(3) 0.043(3) 0.037(2) 0.003(2) 0.020(2) -0.007(2) C5'B 0.051(3) 0.027(2) 0.048(3) -0.003(2) 0.016(2) -0.002(2) C6'B 0.055(3) 0.030(2) 0.041(3) 0.005(2) 0.021(2) -0.008(2) C7'B 0.061(3) 0.035(3) 0.043(3) 0.000(2) 0.018(2) -0.008(3) F7'B 0.0595(19) 0.063(2) 0.059(2) 0.0042(18) 0.0170(16) 0.0076(18) N1'B 0.060(3) 0.027(2) 0.040(2) -0.0083(18) 0.0206(19) 0.003(2) C2'B 0.049(3) 0.032(3) 0.042(3) 0.004(2) 0.022(2) 0.004(2) N2'B 0.079(3) 0.045(2) 0.031(2) -0.002(2) 0.020(2) 0.015(2) N3'B 0.058(3) 0.038(2) 0.042(2) 0.000(2) 0.023(2) 0.001(2) C4'B 0.047(3) 0.038(3) 0.038(3) -0.010(2) 0.011(2) -0.003(2) N4'B 0.058(3) 0.037(2) 0.035(2) 0.0052(19) 0.0153(19) 0.001(2) S1A 0.0578(7) 0.0320(6) 0.0421(6) 0.0009(5) 0.0203(5) -0.0032(6) O1A 0.096(3) 0.047(2) 0.062(2) -0.0206(19) 0.045(2) -0.026(2) O2A 0.083(3) 0.047(2) 0.0435(19) 0.0055(17) 0.0265(18) -0.012(2) O3A 0.052(2) 0.047(2) 0.062(2) 0.0128(18) 0.0293(17) -0.0012(19) S1B 0.0575(7) 0.0323(6) 0.0431(7) 0.0029(6) 0.0225(6) 0.0008(6) O1B 0.100(3) 0.048(2) 0.0293(18) -0.0014(17) 0.0239(18) -0.018(2) O2B 0.091(3) 0.042(2) 0.050(2) -0.0100(18) 0.035(2) -0.012(2) O3B 0.059(2) 0.043(2) 0.048(2) 0.0093(18) 0.0137(18) 0.001(2) C8B 0.039(3) 0.045(3) 0.109(5) 0.023(3) 0.022(3) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C6A 1.360(6) . ? C1A C2A 1.410(7) . ? C1A C5'A 1.503(6) . ? C2A C3A 1.386(8) . ? C2A Cl2A 1.732(5) . ? C3A C4A 1.389(7) . ? C3A Cl3A 1.721(6) . ? C4A C5A 1.394(7) . ? C4A H4A 0.9300 . ? C5A C6A 1.410(7) . ? C5A Cl5A 1.720(5) . ? C6A H6A 0.9300 . ? C5'A C6'A 1.363(6) . ? C5'A C4'A 1.429(6) . ? C6'A N1'A 1.355(6) . ? C6'A C7'A 1.508(6) . ? C7'A F7'A 1.394(6) . ? C7'A H71A 0.9700 . ? C7'A H72A 0.9700 . ? N1'A C2'A 1.350(5) . ? N1'A H1'A 0.846(8) . ? C2'A N2'A 1.317(6) . ? C2'A N3'A 1.344(6) . ? N2'A H21A 0.847(8) . ? N2'A H22A 0.847(9) . ? N3'A C4'A 1.342(6) . ? C4'A N4'A 1.329(5) . ? N4'A H41A 0.848(9) . ? N4'A H42A 0.848(8) . ? C1B C6B 1.384(7) . ? C1B C2B 1.411(7) . ? C1B C5'B 1.468(7) . ? C2B C3B 1.381(7) . ? C2B Cl2B 1.736(6) . ? C3B C4B 1.368(8) . ? C3B Cl3B 1.740(6) . ? C4B C5B 1.346(8) . ? C4B H4B 0.9300 . ? C5B C6B 1.390(7) . ? C5B Cl5B 1.730(6) . ? C6B H6B 0.9300 . ? C5'B C6'B 1.336(7) . ? C5'B C4'B 1.464(7) . ? C6'B N1'B 1.374(6) . ? C6'B C7'B 1.501(7) . ? C7'B F7'B 1.395(6) . ? C7'B H71B 0.9700 . ? C7'B H72B 0.9700 . ? N1'B C2'B 1.349(5) . ? N1'B H1'B 0.829(8) . ? C2'B N3'B 1.311(6) . ? C2'B N2'B 1.337(6) . ? N2'B H21B 0.828(8) . ? N2'B H22B 0.828(9) . ? N3'B C4'B 1.346(6) . ? C4'B N4'B 1.304(6) . ? N4'B H41B 0.829(8) . ? N4'B H42B 0.827(9) . ? S1A O2A 1.442(4) . ? S1A O1A 1.448(4) . ? S1A O3A 1.449(4) . ? S1A C8B 1.727(6) . ? C8A S1B 1.771(7) . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? S1B O3B 1.446(4) . ? S1B O1B 1.448(4) . ? S1B O2B 1.450(4) . ? C8B H8B1 0.9600 . ? C8B H8B2 0.9600 . ? C8B H8B3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6A C1A C2A 119.5(5) . . ? C6A C1A C5'A 118.9(5) . . ? C2A C1A C5'A 121.5(4) . . ? C3A C2A C1A 120.5(5) . . ? C3A C2A Cl2A 119.5(4) . . ? C1A C2A Cl2A 120.0(4) . . ? C2A C3A C4A 120.6(5) . . ? C2A C3A Cl3A 121.6(4) . . ? C4A C3A Cl3A 117.8(4) . . ? C3A C4A C5A 118.2(5) . . ? C3A C4A H4A 120.9 . . ? C5A C4A H4A 120.9 . . ? C4A C5A C6A 121.3(5) . . ? C4A C5A Cl5A 118.8(4) . . ? C6A C5A Cl5A 119.8(4) . . ? C1A C6A C5A 119.7(5) . . ? C1A C6A H6A 120.1 . . ? C5A C6A H6A 120.1 . . ? C6'A C5'A C4'A 116.2(4) . . ? C6'A C5'A C1A 122.5(4) . . ? C4'A C5'A C1A 121.1(4) . . ? N1'A C6'A C5'A 120.2(4) . . ? N1'A C6'A C7'A 114.8(4) . . ? C5'A C6'A C7'A 124.9(4) . . ? F7'A C7'A C6'A 108.2(4) . . ? F7'A C7'A H71A 110.1 . . ? C6'A C7'A H71A 110.1 . . ? F7'A C7'A H72A 110.1 . . ? C6'A C7'A H72A 110.1 . . ? H71A C7'A H72A 108.4 . . ? C2'A N1'A C6'A 121.1(4) . . ? C2'A N1'A H1'A 119.8(6) . . ? C6'A N1'A H1'A 119.2(6) . . ? N2'A C2'A N3'A 117.9(4) . . ? N2'A C2'A N1'A 120.0(4) . . ? N3'A C2'A N1'A 122.1(4) . . ? C2'A N2'A H21A 124.9(9) . . ? C2'A N2'A H22A 124.9(11) . . ? H21A N2'A H22A 110.2(15) . . ? C4'A N3'A C2'A 117.4(4) . . ? N4'A C4'A N3'A 115.5(4) . . ? N4'A C4'A C5'A 121.5(4) . . ? N3'A C4'A C5'A 123.0(4) . . ? C4'A N4'A H41A 123.4(10) . . ? C4'A N4'A H42A 123.3(10) . . ? H41A N4'A H42A 113.2(16) . . ? C6B C1B C2B 117.4(4) . . ? C6B C1B C5'B 121.9(4) . . ? C2B C1B C5'B 120.5(5) . . ? C3B C2B C1B 120.7(5) . . ? C3B C2B Cl2B 120.1(4) . . ? C1B C2B Cl2B 119.1(4) . . ? C4B C3B C2B 119.8(5) . . ? C4B C3B Cl3B 119.9(4) . . ? C2B C3B Cl3B 120.3(5) . . ? C5B C4B C3B 120.7(5) . . ? C5B C4B H4B 119.7 . . ? C3B C4B H4B 119.7 . . ? C4B C5B C6B 120.6(5) . . ? C4B C5B Cl5B 120.0(4) . . ? C6B C5B Cl5B 119.4(4) . . ? C1B C6B C5B 120.8(5) . . ? C1B C6B H6B 119.6 . . ? C5B C6B H6B 119.6 . . ? C6'B C5'B C4'B 115.9(5) . . ? C6'B C5'B C1B 124.3(5) . . ? C4'B C5'B C1B 119.8(4) . . ? C5'B C6'B N1'B 120.7(4) . . ? C5'B C6'B C7'B 126.3(4) . . ? N1'B C6'B C7'B 112.9(4) . . ? F7'B C7'B C6'B 108.3(4) . . ? F7'B C7'B H71B 110.0 . . ? C6'B C7'B H71B 110.0 . . ? F7'B C7'B H72B 110.0 . . ? C6'B C7'B H72B 110.0 . . ? H71B C7'B H72B 108.4 . . ? C2'B N1'B C6'B 120.4(4) . . ? C2'B N1'B H1'B 121.1(6) . . ? C6'B N1'B H1'B 118.4(6) . . ? N3'B C2'B N2'B 120.2(4) . . ? N3'B C2'B N1'B 122.5(4) . . ? N2'B C2'B N1'B 117.2(4) . . ? C2'B N2'B H21B 120.8(9) . . ? C2'B N2'B H22B 120.7(11) . . ? H21B N2'B H22B 115.3(14) . . ? C2'B N3'B C4'B 118.5(4) . . ? N4'B C4'B N3'B 116.4(4) . . ? N4'B C4'B C5'B 122.1(4) . . ? N3'B C4'B C5'B 121.5(5) . . ? C4'B N4'B H41B 123.9(9) . . ? C4'B N4'B H42B 124.6(11) . . ? H41B N4'B H42B 107.9(16) . . ? O2A S1A O1A 111.0(2) . . ? O2A S1A O3A 112.7(2) . . ? O1A S1A O3A 112.6(2) . . ? O2A S1A C8B 105.0(3) . . ? O1A S1A C8B 106.8(3) . . ? O3A S1A C8B 108.3(3) . . ? S1B C8A H8A1 109.5 . . ? S1B C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? S1B C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? O3B S1B O1B 113.7(2) . . ? O3B S1B O2B 112.5(2) . . ? O1B S1B O2B 111.1(2) . . ? O3B S1B C8A 107.1(3) . . ? O1B S1B C8A 106.5(3) . . ? O2B S1B C8A 105.4(3) . . ? S1A C8B H8B1 109.5 . . ? S1A C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? S1A C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 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 C6A C1A C2A C3A 3.0(8) . . . . ? C5'A C1A C2A C3A -179.1(5) . . . . ? C6A C1A C2A Cl2A -178.0(4) . . . . ? C5'A C1A C2A Cl2A -0.1(7) . . . . ? C1A C2A C3A C4A -2.0(9) . . . . ? Cl2A C2A C3A C4A 179.0(4) . . . . ? C1A C2A C3A Cl3A 175.7(4) . . . . ? Cl2A C2A C3A Cl3A -3.3(7) . . . . ? C2A C3A C4A C5A -0.6(8) . . . . ? Cl3A C3A C4A C5A -178.4(4) . . . . ? C3A C4A C5A C6A 2.3(8) . . . . ? C3A C4A C5A Cl5A 179.6(4) . . . . ? C2A C1A C6A C5A -1.3(8) . . . . ? C5'A C1A C6A C5A -179.3(5) . . . . ? C4A C5A C6A C1A -1.3(8) . . . . ? Cl5A C5A C6A C1A -178.6(4) . . . . ? C6A C1A C5'A C6'A -108.4(6) . . . . ? C2A C1A C5'A C6'A 73.7(7) . . . . ? C6A C1A C5'A C4'A 66.0(7) . . . . ? C2A C1A C5'A C4'A -111.9(6) . . . . ? C4'A C5'A C6'A N1'A -0.5(7) . . . . ? C1A C5'A C6'A N1'A 174.2(5) . . . . ? C4'A C5'A C6'A C7'A -178.3(4) . . . . ? C1A C5'A C6'A C7'A -3.6(8) . . . . ? N1'A C6'A C7'A F7'A -61.9(5) . . . . ? C5'A C6'A C7'A F7'A 116.1(5) . . . . ? C5'A C6'A N1'A C2'A -2.6(7) . . . . ? C7'A C6'A N1'A C2'A 175.5(4) . . . . ? C6'A N1'A C2'A N2'A -172.9(5) . . . . ? C6'A N1'A C2'A N3'A 3.7(7) . . . . ? N2'A C2'A N3'A C4'A 175.1(4) . . . . ? N1'A C2'A N3'A C4'A -1.5(7) . . . . ? C2'A N3'A C4'A N4'A 177.8(4) . . . . ? C2'A N3'A C4'A C5'A -1.7(7) . . . . ? C6'A C5'A C4'A N4'A -176.8(4) . . . . ? C1A C5'A C4'A N4'A 8.5(7) . . . . ? C6'A C5'A C4'A N3'A 2.7(7) . . . . ? C1A C5'A C4'A N3'A -172.0(5) . . . . ? C6B C1B C2B C3B -0.8(8) . . . . ? C5'B C1B C2B C3B -175.8(5) . . . . ? C6B C1B C2B Cl2B 177.0(4) . . . . ? C5'B C1B C2B Cl2B 2.0(7) . . . . ? C1B C2B C3B C4B -0.9(8) . . . . ? Cl2B C2B C3B C4B -178.6(4) . . . . ? C1B C2B C3B Cl3B 179.5(4) . . . . ? Cl2B C2B C3B Cl3B 1.8(7) . . . . ? C2B C3B C4B C5B 2.8(9) . . . . ? Cl3B C3B C4B C5B -177.5(4) . . . . ? C3B C4B C5B C6B -3.1(9) . . . . ? C3B C4B C5B Cl5B 178.0(5) . . . . ? C2B C1B C6B C5B 0.6(8) . . . . ? C5'B C1B C6B C5B 175.5(5) . . . . ? C4B C5B C6B C1B 1.3(8) . . . . ? Cl5B C5B C6B C1B -179.7(4) . . . . ? C6B C1B C5'B C6'B -64.3(8) . . . . ? C2B C1B C5'B C6'B 110.4(6) . . . . ? C6B C1B C5'B C4'B 116.2(6) . . . . ? C2B C1B C5'B C4'B -69.0(7) . . . . ? C4'B C5'B C6'B N1'B 3.3(7) . . . . ? C1B C5'B C6'B N1'B -176.2(5) . . . . ? C4'B C5'B C6'B C7'B -179.8(5) . . . . ? C1B C5'B C6'B C7'B 0.7(9) . . . . ? C5'B C6'B C7'B F7'B -112.3(6) . . . . ? N1'B C6'B C7'B F7'B 64.7(5) . . . . ? C5'B C6'B N1'B C2'B 2.8(7) . . . . ? C7'B C6'B N1'B C2'B -174.5(4) . . . . ? C6'B N1'B C2'B N3'B -6.7(7) . . . . ? C6'B N1'B C2'B N2'B 176.7(5) . . . . ? N2'B C2'B N3'B C4'B -179.8(5) . . . . ? N1'B C2'B N3'B C4'B 3.7(7) . . . . ? C2'B N3'B C4'B N4'B -177.8(4) . . . . ? C2'B N3'B C4'B C5'B 2.9(7) . . . . ? C6'B C5'B C4'B N4'B 174.4(5) . . . . ? C1B C5'B C4'B N4'B -6.1(8) . . . . ? C6'B C5'B C4'B N3'B -6.3(7) . . . . ? C1B C5'B C4'B N3'B 173.2(5) . . . . ? 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'A H1'A O2A 0.846(8) 1.928(9) 2.773(5) 178.0(13) . N1'A H1'A S1A 0.846(8) 2.918(8) 3.702(4) 155.2(7) . N2'A H21A O1A 0.847(8) 1.969(10) 2.811(6) 172.5(11) . N2'A H22A F7'B 0.847(9) 2.219(12) 3.038(5) 162.6(16) 1_455 N2'A H21A S1A 0.847(8) 2.960(11) 3.717(4) 149.7(11) . N4'A H42A O2B 0.848(8) 2.003(10) 2.821(5) 161.7(13) 2_646 N4'A H41A O3A 0.848(9) 2.122(11) 2.935(5) 160.4(14) 2_646 N1'B H1'B O1B 0.829(8) 1.943(9) 2.770(5) 175.0(15) 2_745 N2'B H21B O2B 0.828(8) 2.047(15) 2.771(6) 145.8(19) 2_745 N2'B H22B F7'A 0.828(9) 2.236(11) 3.035(5) 162.0(12) 1_554 N2'B H21B S1B 0.828(8) 2.901(12) 3.648(4) 151.1(14) 2_745 N4'B H41B O1A 0.829(8) 2.098(11) 2.855(5) 151.6(15) . N4'B H42B O3B 0.827(9) 2.107(11) 2.916(5) 166.1(16) . _diffrn_measured_fraction_theta_max 0.819 _diffrn_reflns_theta_full 74.42 _diffrn_measured_fraction_theta_full 0.819 _refine_diff_density_max 0.340 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.074 # Attachment '- 4_BW203W92Scif.txt.txt' data_BW203W92(SpaceGrpoupP1) _database_code_depnum_ccdc_archive 'CCDC 299483' _journal_full_name ; Medicinal Chemistry Communications _audit_creation_method SHELXL-97 _chemical_name_systematic 'R-2,4-diamino-6-(fluoromethyl)-5- (2,3,5-trichlorophenyl)pyrimidine' ; _chemical_name_common 'BW203W92 S-enantiomer' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C11 H9 Cl3 F N4 C H3 S O3' _chemical_formula_sum 'C12 H12 Cl3 F N4 O3 S' _chemical_formula_weight 417.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.716(2) _cell_length_b 8.120(2) _cell_length_c 13.719(3) _cell_angle_alpha 74.91(3) _cell_angle_beta 87.69(3) _cell_angle_gamma 89.83(3) _cell_volume 829.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6456 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 _exptl_absorpt_coefficient_mu 0.709 _exptl_absorpt_correction_type SORTAV _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details ; SORTAV absorption correction software package: R.H. Blessing (1997) ; _exptl_special_details ; Oxford Cryosystems Cryostream cooler: J. Cosier and A.M. Glazer (1986) ; _diffrn_ambient_temperature 123(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 'Nonius Kappa CCD' _diffrn_measurement_method 'Denzo,Z. Otwinowski and W. Minor (1997)' _diffrn_detector_area_resol_mean '0.5 deg' _diffrn_standards_number NA _diffrn_standards_interval_count NA _diffrn_standards_interval_time NA _diffrn_standards_decay_% NA _diffrn_reflns_number 6456 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.1655 _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 -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5302 _reflns_number_gt 3177 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Collect Data collection and processing user interface: Collect: Data collection software, R. Hooft, Nonius B.V.(1998) ; _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELX-S (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1998)' _computing_publication_material SHELX97 _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^)+(0.0000P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0070(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.10(9) _refine_ls_number_reflns 5302 _refine_ls_number_parameters 476 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.008 _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 C1A C 0.8110(6) 0.9061(5) 0.5179(3) 0.0254(13) Uani 1 1 d . . . C2A C 0.6398(6) 0.8486(6) 0.5312(4) 0.0328(14) Uani 1 1 d . . . Cl2A Cl 0.56724(17) 0.71241(16) 0.46335(11) 0.0465(4) Uani 1 1 d . . . C3A C 0.5248(7) 0.8967(6) 0.6001(4) 0.0341(15) Uani 1 1 d . . . Cl3A Cl 0.31126(16) 0.82864(17) 0.61514(11) 0.0458(4) Uani 1 1 d . . . C4A C 0.5862(7) 0.9977(6) 0.6590(4) 0.0388(15) Uani 1 1 d . . . H4A H 0.5118 1.0259 0.7090 0.047 Uiso 1 1 calc R . . C5A C 0.7526(7) 1.0561(6) 0.6452(4) 0.0381(15) Uani 1 1 d . . . Cl5A Cl 0.8296(2) 1.18208(16) 0.71911(11) 0.0523(4) Uani 1 1 d . . . C6A C 0.8638(6) 1.0141(6) 0.5747(4) 0.0288(13) Uani 1 1 d . . . H6A H 0.9783 1.0597 0.5647 0.035 Uiso 1 1 calc R . . C5'A C 0.9327(6) 0.8671(6) 0.4403(4) 0.0320(14) Uani 1 1 d . . . C6'A C 1.0125(6) 0.7112(6) 0.4505(4) 0.0312(14) Uani 1 1 d D . . C7A' C 0.9825(7) 0.5549(6) 0.5352(4) 0.0414(16) Uani 1 1 d . . . H7A1 H 0.8886 0.4855 0.5182 0.050 Uiso 1 1 calc R . . H7A2 H 1.0892 0.4855 0.5441 0.050 Uiso 1 1 calc R . . F7A' F 0.9377(4) 0.5961(4) 0.6237(2) 0.0582(10) Uani 1 1 d . . . N1'A N 1.1284(5) 0.6931(5) 0.3768(3) 0.0331(12) Uani 1 1 d D . . C2'A C 1.1672(5) 0.8223(5) 0.2919(3) 0.0287(14) Uani 1 1 d D . . N2'A N 1.2801(5) 0.7916(4) 0.2253(3) 0.0369(13) Uani 1 1 d D . . N3'A N 1.0900(5) 0.9727(5) 0.2790(3) 0.0339(12) Uani 1 1 d . . . C4'A C 0.9752(6) 0.9974(5) 0.3513(4) 0.0350(15) Uani 1 1 d D . . N4'A N 0.9114(5) 1.1536(5) 0.3366(3) 0.0341(12) Uani 1 1 d D . . C1B C 1.3259(7) -0.4393(6) -0.0657(4) 0.0349(15) Uani 1 1 d . . . C2B C 1.2857(6) -0.5342(6) -0.1345(4) 0.0302(14) Uani 1 1 d . . . Cl2B Cl 1.08509(18) -0.63157(16) -0.12849(11) 0.0476(4) Uani 1 1 d . . . C3B C 1.4077(7) -0.5470(6) -0.2084(4) 0.0414(16) Uani 1 1 d . . . Cl3B Cl 1.3611(2) -0.65330(18) -0.29803(11) 0.0585(5) Uani 1 1 d . . . C4B C 1.5717(7) -0.4692(6) -0.2154(4) 0.0387(15) Uani 1 1 d . . . H4B H 1.6559 -0.4782 -0.2662 0.046 Uiso 1 1 calc R . . C5B C 1.6064(7) -0.3786(7) -0.1452(4) 0.0403(16) Uani 1 1 d . . . Cl5B Cl 1.80649(17) -0.28057(17) -0.15428(11) 0.0453(4) Uani 1 1 d . . . C6B C 1.4861(6) -0.3604(6) -0.0717(4) 0.0335(14) Uani 1 1 d . . . H6B H 1.5127 -0.2949 -0.0260 0.040 Uiso 1 1 calc R . . C5'B C 1.1892(6) -0.4172(6) 0.0110(4) 0.0297(14) Uani 1 1 d . . . C6'B C 1.1103(6) -0.2655(6) 0.0038(4) 0.0317(14) Uani 1 1 d D . . C7'B C 1.1414(8) -0.1022(7) -0.0727(4) 0.0411(16) Uani 1 1 d . . . H7B1 H 1.0364 -0.0308 -0.0764 0.049 Uiso 1 1 calc R . . H7B2 H 1.2381 -0.0404 -0.0522 0.049 Uiso 1 1 calc R . . F7'B F 1.1818(4) -0.1277(3) -0.1676(2) 0.0516(10) Uani 1 1 d . . . N1'B N 0.9863(5) -0.2521(5) 0.0762(3) 0.0315(12) Uani 1 1 d D . . C2'B C 0.9423(6) -0.3860(5) 0.1552(3) 0.0312(14) Uani 1 1 d D . . N2'B N 0.8239(5) -0.3629(4) 0.2235(3) 0.0373(13) Uani 1 1 d D . . N3'B N 1.0174(5) -0.5380(5) 0.1673(3) 0.0288(11) Uani 1 1 d . . . C4'B C 1.1345(6) -0.5565(5) 0.0960(4) 0.0306(14) Uani 1 1 d D . . N4'B N 1.2040(5) -0.7116(5) 0.1081(3) 0.0357(12) Uani 1 1 d D . . S1A S 0.46889(16) 0.36830(16) 0.35475(11) 0.0406(4) Uani 1 1 d . . . O1A O 0.6458(5) 0.3664(5) 0.3903(3) 0.0530(12) Uani 1 1 d . . . O2A O 0.3371(5) 0.4114(4) 0.4245(3) 0.0464(11) Uani 1 1 d . . . O3A O 0.4578(5) 0.4757(4) 0.2526(3) 0.0437(11) Uani 1 1 d . . . C8A C 0.4213(7) 0.1623(6) 0.3510(4) 0.0414(16) Uani 1 1 d . . . H8A1 H 0.3070 0.1594 0.3228 0.062 Uiso 1 1 calc R . . H8A2 H 0.4205 0.0868 0.4196 0.062 Uiso 1 1 calc R . . H8A3 H 0.5093 0.1239 0.3085 0.062 Uiso 1 1 calc R . . S1B S 0.63243(17) 0.05674(16) 0.08231(11) 0.0383(4) Uani 1 1 d . . . O3B O 0.6584(5) -0.0367(4) 0.1867(3) 0.0418(11) Uani 1 1 d . . . O1B O 0.4523(4) 0.0590(4) 0.0562(3) 0.0437(11) Uani 1 1 d . . . O2B O 0.7488(5) -0.0010(5) 0.0118(3) 0.0512(12) Uani 1 1 d . . . C8B C 0.6921(8) 0.2668(7) 0.0721(5) 0.058(2) Uani 1 1 d . . . H8B1 H 0.6827 0.3340 0.0020 0.087 Uiso 1 1 calc R . . H8B2 H 0.8122 0.2707 0.0922 0.087 Uiso 1 1 calc R . . H8B3 H 0.6152 0.3143 0.1163 0.087 Uiso 1 1 calc R . . H21A H 1.3568(10) 0.7124(14) 0.2416(12) 0.042(15) Uiso 1 1 d D . . H22A H 1.3440(13) 0.8719(16) 0.1871(10) 0.030(13) Uiso 1 1 d D . . H41A H 0.948(3) 1.2326(10) 0.2845(11) 0.026(13) Uiso 1 1 d D . . H42A H 0.8321(14) 1.1740(15) 0.3778(11) 0.022(12) Uiso 1 1 d D . . H1'A H 1.1970(16) 0.6063(14) 0.3893(12) 0.11(3) Uiso 1 1 d D . . H21B H 0.7600(11) -0.2694(12) 0.2099(11) 0.036(14) Uiso 1 1 d D . . H22B H 0.7989(17) -0.4465(16) 0.2779(7) 0.020(12) Uiso 1 1 d D . . H41B H 1.2784(14) -0.7292(13) 0.0612(9) 0.11(3) Uiso 1 1 d D . . H42B H 1.204(3) -0.7815(14) 0.1694(8) 0.21(5) Uiso 1 1 d D . . H1'B H 0.9093(11) -0.1708(12) 0.0572(7) 0.013(11) Uiso 1 1 d 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 C1A 0.030(3) 0.023(2) 0.024(3) -0.006(2) -0.006(2) 0.002(2) C2A 0.039(3) 0.030(3) 0.029(3) -0.006(2) -0.005(2) 0.005(2) Cl2A 0.0424(8) 0.0486(7) 0.0572(9) -0.0301(6) 0.0006(7) 0.0016(6) C3A 0.043(3) 0.024(2) 0.031(3) 0.002(2) 0.000(2) 0.004(2) Cl3A 0.0346(7) 0.0493(8) 0.0539(9) -0.0152(7) 0.0030(7) 0.0050(6) C4A 0.047(3) 0.033(3) 0.032(3) -0.002(2) 0.009(3) 0.008(3) C5A 0.058(3) 0.026(2) 0.038(3) -0.021(2) -0.002(3) 0.009(3) Cl5A 0.0739(10) 0.0421(7) 0.0483(9) -0.0242(6) -0.0085(8) 0.0051(7) C6A 0.028(3) 0.028(2) 0.035(3) -0.015(2) -0.012(2) 0.004(2) C5'A 0.038(3) 0.020(2) 0.037(3) -0.006(2) 0.005(2) 0.003(2) C6'A 0.025(3) 0.037(3) 0.032(3) -0.011(2) -0.006(2) 0.002(2) C7A' 0.059(3) 0.034(3) 0.030(3) -0.007(2) 0.003(3) 0.017(3) F7A' 0.074(2) 0.0459(17) 0.051(2) -0.0080(16) 0.0125(18) 0.0155(17) N1'A 0.029(2) 0.032(2) 0.035(3) -0.004(2) -0.001(2) 0.005(2) C2'A 0.022(3) 0.027(2) 0.040(3) -0.012(2) -0.009(2) 0.000(2) N2'A 0.035(2) 0.030(2) 0.043(3) -0.006(2) 0.012(2) 0.003(2) N3'A 0.035(2) 0.029(2) 0.041(3) -0.0148(19) 0.002(2) 0.007(2) C4'A 0.031(3) 0.032(3) 0.045(3) -0.015(2) -0.004(3) 0.007(2) N4'A 0.029(2) 0.031(2) 0.036(3) 0.001(2) 0.012(2) 0.005(2) C1B 0.042(3) 0.025(2) 0.038(3) -0.010(2) -0.004(3) 0.010(2) C2B 0.030(3) 0.028(2) 0.036(3) -0.013(2) -0.010(2) 0.003(2) Cl2B 0.0494(8) 0.0434(7) 0.0574(9) -0.0252(6) -0.0109(7) 0.0053(7) C3B 0.056(3) 0.031(3) 0.042(3) -0.016(2) -0.021(3) 0.023(3) Cl3B 0.0726(10) 0.0618(8) 0.0542(9) -0.0376(7) -0.0120(8) 0.0241(8) C4B 0.040(3) 0.035(3) 0.037(3) -0.004(2) 0.005(3) 0.020(3) C5B 0.032(3) 0.038(3) 0.045(4) -0.002(3) 0.002(3) 0.010(3) Cl5B 0.0372(7) 0.0500(8) 0.0454(8) -0.0073(7) 0.0025(6) 0.0031(7) C6B 0.036(3) 0.040(3) 0.029(3) -0.014(2) -0.006(2) 0.010(3) C5'B 0.027(3) 0.032(3) 0.030(3) -0.008(2) -0.002(2) 0.007(2) C6'B 0.033(3) 0.028(3) 0.033(3) -0.006(2) -0.010(2) 0.000(2) C7'B 0.050(3) 0.043(3) 0.028(3) -0.007(3) 0.002(3) -0.002(3) F7'B 0.072(2) 0.0369(17) 0.0421(19) -0.0057(14) 0.0105(17) 0.0127(16) N1'B 0.035(2) 0.024(2) 0.035(3) -0.0075(18) 0.001(2) 0.0086(19) C2'B 0.035(3) 0.038(3) 0.023(3) -0.011(2) -0.005(2) 0.002(2) N2'B 0.044(3) 0.025(2) 0.042(3) -0.007(2) 0.007(2) 0.016(2) N3'B 0.031(2) 0.023(2) 0.032(2) -0.0057(18) 0.0017(19) 0.0074(18) C4'B 0.027(3) 0.025(2) 0.041(3) -0.010(2) -0.009(2) 0.008(2) N4'B 0.046(3) 0.027(2) 0.035(3) -0.0095(19) -0.002(2) 0.006(2) S1A 0.0371(8) 0.0352(7) 0.0554(9) -0.0224(6) -0.0027(7) 0.0076(7) O1A 0.039(2) 0.053(2) 0.079(3) -0.039(2) -0.008(2) 0.0078(19) O2A 0.044(2) 0.045(2) 0.053(2) -0.0185(18) -0.0001(19) 0.0187(18) O3A 0.051(2) 0.0327(19) 0.043(2) -0.0035(17) 0.0050(19) 0.0030(18) C8A 0.038(3) 0.040(3) 0.047(4) -0.011(3) -0.009(3) 0.005(3) S1B 0.0391(7) 0.0357(7) 0.0421(8) -0.0147(6) 0.0023(7) 0.0097(6) O3B 0.058(2) 0.0283(18) 0.038(2) -0.0085(16) 0.0066(19) 0.0109(18) O1B 0.0267(18) 0.051(2) 0.058(2) -0.0235(19) -0.0054(18) 0.0130(17) O2B 0.060(2) 0.053(2) 0.035(2) -0.0025(19) 0.0028(19) 0.027(2) C8B 0.055(4) 0.031(3) 0.083(5) -0.005(3) -0.009(4) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C6A 1.387(7) . ? C1A C2A 1.392(7) . ? C1A C5'A 1.486(7) . ? C2A C3A 1.399(7) . ? C2A Cl2A 1.727(5) . ? C3A C4A 1.388(8) . ? C3A Cl3A 1.727(5) . ? C4A C5A 1.359(8) . ? C4A H4A 0.9500 . ? C5A C6A 1.375(7) . ? C5A Cl5A 1.738(6) . ? C6A H6A 0.9500 . ? C5'A C6'A 1.383(6) . ? C5'A C4'A 1.420(6) . ? C6'A N1'A 1.359(6) . ? C6'A C7A' 1.492(6) . ? C7A' F7A' 1.372(6) . ? C7A' H7A1 0.9900 . ? C7A' H7A2 0.9900 . ? N1'A C2'A 1.373(5) . ? N1'A H1'A 0.865(8) . ? C2'A N2'A 1.308(6) . ? C2'A N3'A 1.330(5) . ? N2'A H21A 0.864(8) . ? N2'A H22A 0.864(8) . ? N3'A C4'A 1.356(6) . ? C4'A N4'A 1.328(5) . ? N4'A H41A 0.864(9) . ? N4'A H42A 0.861(8) . ? C1B C6B 1.383(7) . ? C1B C2B 1.409(7) . ? C1B C5'B 1.504(7) . ? C2B C3B 1.380(7) . ? C2B Cl2B 1.729(5) . ? C3B C4B 1.405(8) . ? C3B Cl3B 1.725(6) . ? C4B C5B 1.390(8) . ? C4B H4B 0.9500 . ? C5B C6B 1.379(7) . ? C5B Cl5B 1.724(6) . ? C6B H6B 0.9500 . ? C5'B C6'B 1.354(6) . ? C5'B C4'B 1.447(6) . ? C6'B N1'B 1.375(6) . ? C6'B C7'B 1.475(6) . ? C7'B F7'B 1.394(6) . ? C7'B H7B1 0.9900 . ? C7'B H7B2 0.9900 . ? N1'B C2'B 1.354(5) . ? N1'B H1'B 0.882(7) . ? C2'B N2'B 1.330(5) . ? C2'B N3'B 1.336(5) . ? N2'B H21B 0.886(7) . ? N2'B H22B 0.884(8) . ? N3'B C4'B 1.342(6) . ? C4'B N4'B 1.340(5) . ? N4'B H41B 0.884(8) . ? N4'B H42B 0.884(8) . ? S1A O3A 1.451(4) . ? S1A O1A 1.467(4) . ? S1A O2A 1.471(4) . ? S1A C8A 1.728(5) . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? S1B O1B 1.448(4) . ? S1B O3B 1.458(4) . ? S1B O2B 1.458(4) . ? S1B C8B 1.737(6) . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 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 C6A C1A C2A 117.8(4) . . ? C6A C1A C5'A 119.6(4) . . ? C2A C1A C5'A 122.4(5) . . ? C1A C2A C3A 121.2(5) . . ? C1A C2A Cl2A 119.9(4) . . ? C3A C2A Cl2A 118.9(4) . . ? C4A C3A C2A 118.8(5) . . ? C4A C3A Cl3A 119.9(4) . . ? C2A C3A Cl3A 121.3(4) . . ? C5A C4A C3A 120.1(5) . . ? C5A C4A H4A 120.0 . . ? C3A C4A H4A 120.0 . . ? C4A C5A C6A 121.0(5) . . ? C4A C5A Cl5A 120.1(4) . . ? C6A C5A Cl5A 118.9(4) . . ? C5A C6A C1A 120.9(5) . . ? C5A C6A H6A 119.5 . . ? C1A C6A H6A 119.5 . . ? C6'A C5'A C4'A 117.1(4) . . ? C6'A C5'A C1A 123.8(4) . . ? C4'A C5'A C1A 119.0(4) . . ? N1'A C6'A C5'A 118.6(4) . . ? N1'A C6'A C7A' 115.0(4) . . ? C5'A C6'A C7A' 126.4(4) . . ? F7A' C7A' C6'A 111.2(4) . . ? F7A' C7A' H7A1 109.4 . . ? C6'A C7A' H7A1 109.4 . . ? F7A' C7A' H7A2 109.4 . . ? C6'A C7A' H7A2 109.4 . . ? H7A1 C7A' H7A2 108.0 . . ? C6'A N1'A C2'A 122.7(4) . . ? C6'A N1'A H1'A 118.7(10) . . ? C2'A N1'A H1'A 117.2(9) . . ? N2'A C2'A N3'A 122.0(4) . . ? N2'A C2'A N1'A 117.9(4) . . ? N3'A C2'A N1'A 120.1(4) . . ? C2'A N2'A H21A 121.7(10) . . ? C2'A N2'A H22A 121.4(10) . . ? H21A N2'A H22A 99.8(12) . . ? C2'A N3'A C4'A 119.2(4) . . ? N4'A C4'A N3'A 116.1(4) . . ? N4'A C4'A C5'A 121.6(4) . . ? N3'A C4'A C5'A 122.2(4) . . ? C4'A N4'A H41A 119.3(10) . . ? C4'A N4'A H42A 119.7(9) . . ? H41A N4'A H42A 120.9(14) . . ? C6B C1B C2B 120.6(5) . . ? C6B C1B C5'B 120.2(5) . . ? C2B C1B C5'B 119.1(5) . . ? C3B C2B C1B 119.2(5) . . ? C3B C2B Cl2B 119.9(4) . . ? C1B C2B Cl2B 120.9(4) . . ? C2B C3B C4B 121.2(5) . . ? C2B C3B Cl3B 121.0(4) . . ? C4B C3B Cl3B 117.8(4) . . ? C5B C4B C3B 117.6(5) . . ? C5B C4B H4B 121.2 . . ? C3B C4B H4B 121.2 . . ? C6B C5B C4B 122.7(5) . . ? C6B C5B Cl5B 119.5(5) . . ? C4B C5B Cl5B 117.8(4) . . ? C5B C6B C1B 118.8(5) . . ? C5B C6B H6B 120.6 . . ? C1B C6B H6B 120.6 . . ? C6'B C5'B C4'B 116.5(4) . . ? C6'B C5'B C1B 121.6(4) . . ? C4'B C5'B C1B 121.9(4) . . ? C5'B C6'B N1'B 119.2(4) . . ? C5'B C6'B C7'B 128.5(4) . . ? N1'B C6'B C7'B 112.2(4) . . ? F7'B C7'B C6'B 111.4(4) . . ? F7'B C7'B H7B1 109.3 . . ? C6'B C7'B H7B1 109.3 . . ? F7'B C7'B H7B2 109.3 . . ? C6'B C7'B H7B2 109.3 . . ? H7B1 C7'B H7B2 108.0 . . ? C2'B N1'B C6'B 121.8(4) . . ? C2'B N1'B H1'B 118.0(6) . . ? C6'B N1'B H1'B 115.9(6) . . ? N2'B C2'B N3'B 119.7(3) . . ? N2'B C2'B N1'B 118.5(4) . . ? N3'B C2'B N1'B 121.8(4) . . ? C2'B N2'B H21B 119.5(9) . . ? C2'B N2'B H22B 119.9(9) . . ? H21B N2'B H22B 120.1(13) . . ? C2'B N3'B C4'B 117.7(4) . . ? N4'B C4'B N3'B 116.7(4) . . ? N4'B C4'B C5'B 120.5(4) . . ? N3'B C4'B C5'B 122.9(4) . . ? C4'B N4'B H41B 118.9(8) . . ? C4'B N4'B H42B 118.9(9) . . ? H41B N4'B H42B 118.8(15) . . ? O3A S1A O1A 111.3(2) . . ? O3A S1A O2A 112.2(2) . . ? O1A S1A O2A 113.3(2) . . ? O3A S1A C8A 107.1(3) . . ? O1A S1A C8A 106.7(2) . . ? O2A S1A C8A 105.7(2) . . ? S1A C8A H8A1 109.5 . . ? S1A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? S1A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? O1B S1B O3B 112.5(2) . . ? O1B S1B O2B 113.1(2) . . ? O3B S1B O2B 111.9(2) . . ? O1B S1B C8B 106.7(3) . . ? O3B S1B C8B 106.4(3) . . ? O2B S1B C8B 105.6(3) . . ? S1B C8B H8B1 109.5 . . ? S1B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? S1B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 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 C6A C1A C2A C3A -0.6(6) . . . . ? C5'A C1A C2A C3A -175.6(4) . . . . ? C6A C1A C2A Cl2A -179.4(3) . . . . ? C5'A C1A C2A Cl2A 5.5(6) . . . . ? C1A C2A C3A C4A -2.8(7) . . . . ? Cl2A C2A C3A C4A 176.1(4) . . . . ? C1A C2A C3A Cl3A 178.9(3) . . . . ? Cl2A C2A C3A Cl3A -2.2(5) . . . . ? C2A C3A C4A C5A 3.8(7) . . . . ? Cl3A C3A C4A C5A -177.9(4) . . . . ? C3A C4A C5A C6A -1.3(7) . . . . ? C3A C4A C5A Cl5A -179.9(4) . . . . ? C4A C5A C6A C1A -2.2(7) . . . . ? Cl5A C5A C6A C1A 176.4(3) . . . . ? C2A C1A C6A C5A 3.1(6) . . . . ? C5'A C1A C6A C5A 178.3(4) . . . . ? C6A C1A C5'A C6'A 107.9(6) . . . . ? C2A C1A C5'A C6'A -77.1(7) . . . . ? C6A C1A C5'A C4'A -70.1(6) . . . . ? C2A C1A C5'A C4'A 104.8(6) . . . . ? C4'A C5'A C6'A N1'A 1.5(7) . . . . ? C1A C5'A C6'A N1'A -176.6(5) . . . . ? C4'A C5'A C6'A C7A' -177.4(5) . . . . ? C1A C5'A C6'A C7A' 4.5(9) . . . . ? N1'A C6'A C7A' F7A' 150.9(4) . . . . ? C5'A C6'A C7A' F7A' -30.2(8) . . . . ? C5'A C6'A N1'A C2'A -1.2(7) . . . . ? C7A' C6'A N1'A C2'A 177.8(5) . . . . ? C6'A N1'A C2'A N2'A -179.7(4) . . . . ? C6'A N1'A C2'A N3'A -0.1(7) . . . . ? N2'A C2'A N3'A C4'A -179.4(5) . . . . ? N1'A C2'A N3'A C4'A 1.0(7) . . . . ? C2'A N3'A C4'A N4'A 175.9(4) . . . . ? C2'A N3'A C4'A C5'A -0.7(7) . . . . ? C6'A C5'A C4'A N4'A -176.9(5) . . . . ? C1A C5'A C4'A N4'A 1.2(8) . . . . ? C6'A C5'A C4'A N3'A -0.6(8) . . . . ? C1A C5'A C4'A N3'A 177.6(5) . . . . ? C6B C1B C2B C3B -0.3(7) . . . . ? C5'B C1B C2B C3B 176.5(4) . . . . ? C6B C1B C2B Cl2B -179.3(4) . . . . ? C5'B C1B C2B Cl2B -2.5(6) . . . . ? C1B C2B C3B C4B 0.9(7) . . . . ? Cl2B C2B C3B C4B 179.9(4) . . . . ? C1B C2B C3B Cl3B -177.0(4) . . . . ? Cl2B C2B C3B Cl3B 2.1(6) . . . . ? C2B C3B C4B C5B -0.2(7) . . . . ? Cl3B C3B C4B C5B 177.8(4) . . . . ? C3B C4B C5B C6B -1.2(7) . . . . ? C3B C4B C5B Cl5B -179.2(4) . . . . ? C4B C5B C6B C1B 1.8(7) . . . . ? Cl5B C5B C6B C1B 179.7(4) . . . . ? C2B C1B C6B C5B -1.0(7) . . . . ? C5'B C1B C6B C5B -177.8(4) . . . . ? C6B C1B C5'B C6'B 68.9(7) . . . . ? C2B C1B C5'B C6'B -108.0(6) . . . . ? C6B C1B C5'B C4'B -111.4(5) . . . . ? C2B C1B C5'B C4'B 71.7(6) . . . . ? C4'B C5'B C6'B N1'B 0.4(7) . . . . ? C1B C5'B C6'B N1'B -179.9(5) . . . . ? C4'B C5'B C6'B C7'B 178.8(5) . . . . ? C1B C5'B C6'B C7'B -1.5(9) . . . . ? C5'B C6'B C7'B F7'B 35.2(8) . . . . ? N1'B C6'B C7'B F7'B -146.4(4) . . . . ? C5'B C6'B N1'B C2'B 0.8(7) . . . . ? C7'B C6'B N1'B C2'B -177.8(5) . . . . ? C6'B N1'B C2'B N2'B 178.6(4) . . . . ? C6'B N1'B C2'B N3'B 0.2(7) . . . . ? N2'B C2'B N3'B C4'B 179.1(4) . . . . ? N1'B C2'B N3'B C4'B -2.5(7) . . . . ? C2'B N3'B C4'B N4'B -177.9(4) . . . . ? C2'B N3'B C4'B C5'B 3.8(7) . . . . ? C6'B C5'B C4'B N4'B 179.0(5) . . . . ? C1B C5'B C4'B N4'B -0.7(7) . . . . ? C6'B C5'B C4'B N3'B -2.8(7) . . . . ? C1B C5'B C4'B N3'B 177.5(5) . . . . ? 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'A H1'A O2A 0.865(8) 1.882(9) 2.745(5) 176.1(13) 1_655 N1'A H1'A S1A 0.865(8) 2.955(9) 3.776(4) 159.1(12) 1_655 N2'A H22A O1B 0.864(8) 2.167(10) 3.001(5) 162.2(14) 1_665 N2'A H22A O3B 0.864(8) 2.539(11) 3.203(5) 134.4(11) 1_665 N2'A H22A S1B 0.864(8) 2.812(8) 3.644(4) 162.0(10) 1_665 N2'A H21A O3A 0.864(8) 2.044(10) 2.849(5) 154.8(13) 1_655 N2'A H21A S1A 0.864(8) 2.967(10) 3.753(4) 152.3(9) 1_655 N4'A H42A O1A 0.861(8) 2.155(9) 2.872(5) 140.5(12) 1_565 N4'A H41A N4'B 0.864(9) 3.004(14) 3.712(5) 140.6(11) 1_575 N1'B H1'B O2B 0.882(7) 1.851(8) 2.733(5) 177.6(11) . N1'B H1'B S1B 0.882(7) 2.889(8) 3.715(4) 156.7(8) . N2'B H22B O1A 0.884(8) 2.174(10) 3.017(5) 159.4(13) 1_545 N2'B H21B O3B 0.886(7) 1.996(8) 2.869(5) 168.4(12) . N2'B H21B S1B 0.886(7) 2.959(10) 3.782(4) 155.3(11) . N2'B H22B S1A 0.884(8) 2.973(12) 3.619(4) 131.5(12) 1_545 N4'B H41B O1B 0.884(8) 2.191(9) 2.864(5) 132.6(10) 1_645 N4'B H42B N4'A 0.884(8) 3.10(2) 3.712(5) 128.2(18) 1_535 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.373 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.083