# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_2005sot0745 _database_code_depnum_ccdc_archive 'CCDC 603100' _chemical_compound_source 'Suad Rashdan' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H54 N9 O23 P5' _chemical_formula_weight 1171.76 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.313(5) _cell_length_b 13.411(5) _cell_length_c 14.405(5) _cell_angle_alpha 80.288(5) _cell_angle_beta 76.135(5) _cell_angle_gamma 84.352(5) _cell_volume 2456.6(16) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8914 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8958 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 7474 reflections reduced R(int) from 0.1043 to 0.0737 Ratio of minimum to maximum apparent transmission: 0.362422 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31557 _diffrn_reflns_av_R_equivalents 0.2536 _diffrn_reflns_av_sigmaI/netI 0.4710 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10375 _reflns_number_gt 3056 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0522P)^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 10375 _refine_ls_number_parameters 700 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.3281 _refine_ls_R_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 11.622 _refine_ls_shift/su_max 0.086 _refine_ls_shift/su_mean 0.001 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 O101 O 0.50090(18) 0.1291(2) 0.43476(19) 0.0353(10) Uani 1 1 d . . . N101 N 0.4598(2) 0.0284(2) 0.3102(2) 0.0232(11) Uani 1 1 d . . . H101 H 0.4426 0.0820 0.3397 0.028 Uiso 1 1 calc R . . N102 N 0.6158(2) 0.0119(2) 0.3616(2) 0.0260(12) Uani 1 1 d . . . H102 H 0.6790 -0.0165 0.3554 0.031 Uiso 1 1 calc R . . N103 N 0.6679(2) 0.1117(2) 0.4532(2) 0.0264(12) Uani 1 1 d . . . H503 H 0.7280 0.0790 0.4339 0.032 Uiso 1 1 calc R . . C101 C 0.6785(3) -0.1705(3) 0.2752(3) 0.0416(17) Uani 1 1 d . . . H10A H 0.6778 -0.1965 0.3432 0.062 Uiso 1 1 calc R . . H10B H 0.7367 -0.1269 0.2480 0.062 Uiso 1 1 calc R . . H10C H 0.6863 -0.2273 0.2388 0.062 Uiso 1 1 calc R . . C102 C 0.5790(3) -0.1104(3) 0.2686(3) 0.0252(14) Uani 1 1 d . . . C103 C 0.5090(3) -0.1375(3) 0.2217(3) 0.0303(15) Uani 1 1 d . . . H103 H 0.5251 -0.1962 0.1907 0.036 Uiso 1 1 calc R . . C104 C 0.4158(3) -0.0817(3) 0.2185(3) 0.0259(14) Uani 1 1 d . . . H104 H 0.3689 -0.1015 0.1855 0.031 Uiso 1 1 calc R . . C105 C 0.3935(3) 0.0006(3) 0.2630(3) 0.0299(15) Uani 1 1 d . . . H105 H 0.3304 0.0398 0.2612 0.036 Uiso 1 1 calc R . . C106 C 0.5506(3) -0.0225(3) 0.3137(3) 0.0236(14) Uani 1 1 d . . . C107 C 0.5879(3) 0.0887(3) 0.4191(3) 0.0254(14) Uani 1 1 d . . . C108 C 0.6655(3) 0.1824(3) 0.5163(3) 0.0231(14) Uani 1 1 d . . . C109 C 0.5846(3) 0.2529(3) 0.5378(3) 0.0268(14) Uani 1 1 d . . . H109 H 0.5267 0.2568 0.5094 0.032 Uiso 1 1 calc R . . C110 C 0.5888(3) 0.3188(3) 0.6021(3) 0.0310(15) Uani 1 1 d . . . H110 H 0.5319 0.3660 0.6192 0.037 Uiso 1 1 calc R . . C111 C 0.6745(3) 0.3162(3) 0.6410(3) 0.0319(15) Uani 1 1 d . . . H111 H 0.6779 0.3625 0.6832 0.038 Uiso 1 1 calc R . . C112 C 0.7547(3) 0.2453(3) 0.6176(3) 0.0300(15) Uani 1 1 d . . . H112 H 0.8133 0.2420 0.6451 0.036 Uiso 1 1 calc R . . C113 C 0.7517(3) 0.1793(3) 0.5554(3) 0.0269(14) Uani 1 1 d . . . H113 H 0.8083 0.1317 0.5390 0.032 Uiso 1 1 calc R . . O201 O 0.82844(19) 0.19675(19) 0.24527(18) 0.0341(10) Uani 1 1 d . . . N201 N 0.8928(2) 0.3080(2) 0.35003(19) 0.0214(11) Uani 1 1 d . . . H201 H 0.9074 0.2583 0.3151 0.026 Uiso 1 1 calc R . . N202 N 0.7375(2) 0.3381(2) 0.2985(2) 0.0266(12) Uani 1 1 d . . . H202 H 0.6815 0.3782 0.2959 0.032 Uiso 1 1 calc R . . N203 N 0.6735(2) 0.2501(2) 0.2040(2) 0.0261(12) Uani 1 1 d . . . H603 H 0.6231 0.2977 0.2115 0.031 Uiso 1 1 calc R . . C201 C 0.6807(3) 0.5100(3) 0.4035(3) 0.0346(16) Uani 1 1 d . . . H20A H 0.6721 0.5569 0.4505 0.052 Uiso 1 1 calc R . . H20B H 0.6213 0.4674 0.4204 0.052 Uiso 1 1 calc R . . H20C H 0.6850 0.5486 0.3387 0.052 Uiso 1 1 calc R . . C202 C 0.7793(3) 0.4434(3) 0.4047(3) 0.0246(14) Uani 1 1 d . . . C203 C 0.8495(3) 0.4603(3) 0.4554(3) 0.0271(14) Uani 1 1 d . . . H203 H 0.8348 0.5135 0.4936 0.033 Uiso 1 1 calc R . . C204 C 0.9425(3) 0.4005(3) 0.4519(3) 0.0275(14) Uani 1 1 d . . . H204 H 0.9907 0.4137 0.4867 0.033 Uiso 1 1 calc R . . C205 C 0.9630(3) 0.3246(3) 0.3992(3) 0.0243(14) Uani 1 1 d . . . H205 H 1.0255 0.2832 0.3964 0.029 Uiso 1 1 calc R . . C206 C 0.8019(3) 0.3629(3) 0.3512(3) 0.0204(13) Uani 1 1 d . . . C207 C 0.7521(3) 0.2562(3) 0.2489(3) 0.0271(14) Uani 1 1 d . . . C208 C 0.6631(3) 0.1771(3) 0.1469(3) 0.0267(14) Uani 1 1 d . . . C209 C 0.7364(3) 0.0997(3) 0.1256(3) 0.0258(14) Uani 1 1 d . . . H209 H 0.7977 0.0916 0.1495 0.031 Uiso 1 1 calc R . . C210 C 0.7177(3) 0.0334(3) 0.0676(3) 0.0316(15) Uani 1 1 d . . . H210 H 0.7675 -0.0205 0.0521 0.038 Uiso 1 1 calc R . . C211 C 0.6300(3) 0.0436(3) 0.0324(3) 0.0310(15) Uani 1 1 d . . . H211 H 0.6195 -0.0020 -0.0077 0.037 Uiso 1 1 calc R . . C212 C 0.5571(3) 0.1209(3) 0.0561(3) 0.0349(15) Uani 1 1 d . . . H212 H 0.4950 0.1274 0.0335 0.042 Uiso 1 1 calc R . . C213 C 0.5734(3) 0.1894(3) 0.1125(3) 0.0307(15) Uani 1 1 d . . . H213 H 0.5238 0.2437 0.1272 0.037 Uiso 1 1 calc R . . O301 O 0.83629(18) 0.47434(19) 0.09173(18) 0.0305(10) Uani 1 1 d . . . N301 N 0.7967(2) 0.3516(2) -0.0154(2) 0.0245(11) Uani 1 1 d . . . H301 H 0.7752 0.4033 0.0161 0.029 Uiso 1 1 calc R . . N303 N 0.9969(2) 0.4471(2) 0.1288(2) 0.0237(11) Uani 1 1 d . . . H703 H 1.0552 0.4096 0.1160 0.028 Uiso 1 1 calc R . . C301 C 1.0251(3) 0.1622(3) -0.0487(3) 0.0355(16) Uani 1 1 d . . . H30A H 1.0191 0.1275 0.0178 0.053 Uiso 1 1 calc R . . H30B H 1.0811 0.2089 -0.0650 0.053 Uiso 1 1 calc R . . H30C H 1.0406 0.1121 -0.0932 0.053 Uiso 1 1 calc R . . C302 C 0.9246(3) 0.2209(3) -0.0574(3) 0.0229(14) Uani 1 1 d . . . C303 C 0.8616(3) 0.1924(3) -0.1108(3) 0.0253(14) Uani 1 1 d . . . H303 H 0.8840 0.1366 -0.1451 0.030 Uiso 1 1 calc R . . C304 C 0.7655(3) 0.2435(3) -0.1159(3) 0.0304(15) Uani 1 1 d . . . H304 H 0.7235 0.2232 -0.1535 0.036 Uiso 1 1 calc R . . C305 C 0.7335(3) 0.3228(3) -0.0659(3) 0.0254(14) Uani 1 1 d . . . H305 H 0.6678 0.3575 -0.0664 0.031 Uiso 1 1 calc R . . C306 C 0.8906(3) 0.3055(3) -0.0104(2) 0.0236(14) Uani 1 1 d . . . C307 C 0.9201(3) 0.4279(3) 0.0894(3) 0.0241(14) Uani 1 1 d . . . C308 C 0.9936(3) 0.5208(3) 0.1880(3) 0.0223(14) Uani 1 1 d . . . C309 C 0.9129(3) 0.5934(3) 0.2067(3) 0.0266(14) Uani 1 1 d . . . H309 H 0.8549 0.5963 0.1785 0.032 Uiso 1 1 calc R . . C310 C 0.9188(3) 0.6626(3) 0.2681(3) 0.0267(14) Uani 1 1 d . . . H310 H 0.8640 0.7130 0.2809 0.032 Uiso 1 1 calc R . . C311 C 1.0012(3) 0.6594(3) 0.3100(3) 0.0278(15) Uani 1 1 d . . . H311 H 1.0032 0.7062 0.3522 0.033 Uiso 1 1 calc R . . C312 C 1.0822(3) 0.5867(3) 0.2901(3) 0.0283(15) Uani 1 1 d . . . H312 H 1.1403 0.5843 0.3181 0.034 Uiso 1 1 calc R . . C313 C 1.0785(3) 0.5180(3) 0.2296(3) 0.0256(14) Uani 1 1 d . . . H313 H 1.1340 0.4685 0.2164 0.031 Uiso 1 1 calc R . . N302 N 0.9492(2) 0.3433(2) 0.0395(2) 0.0232(11) Uani 1 1 d . . . H302 H 1.0104 0.3125 0.0411 0.028 Uiso 1 1 calc R . . P1 P 0.44937(8) -0.52321(8) 0.83257(8) 0.0255(4) Uani 1 1 d . . . O1 O 0.56658(17) -0.54873(18) 0.83342(18) 0.0301(10) Uani 1 1 d . . . H901 H 0.6001 -0.4970 0.8094 0.045 Uiso 1 1 calc R . . O2 O 0.40537(18) -0.61746(18) 0.82218(17) 0.0301(10) Uani 1 1 d . . . O3 O 0.39353(17) -0.48961(18) 0.93459(17) 0.0254(9) Uani 1 1 d . . . H3 H 0.3628 -0.5385 0.9709 0.038 Uiso 1 1 calc R . . O4 O 0.44055(17) -0.43287(18) 0.75625(17) 0.0263(9) Uani 1 1 d . . . P2 P 0.69084(8) -0.33601(8) 0.66878(7) 0.0249(4) Uani 1 1 d . . . O5 O 0.79170(17) -0.34947(18) 0.59691(17) 0.0261(9) Uani 1 1 d . . . O6 O 0.68446(17) -0.39543(18) 0.76919(17) 0.0257(9) Uani 1 1 d D . . O7 O 0.60290(18) -0.36451(19) 0.62580(17) 0.0325(10) Uani 1 1 d . . . H907 H 0.5513 -0.3803 0.6708 0.049 Uiso 1 1 calc R . . O8 O 0.67041(18) -0.22067(18) 0.68194(17) 0.0291(10) Uani 1 1 d . . . H8 H 0.7110 -0.1856 0.6375 0.044 Uiso 1 1 calc R . . P3 P 0.85605(8) -0.11864(8) 0.45721(8) 0.0258(4) Uani 1 1 d . . . O9 O 0.97513(17) -0.13711(18) 0.44601(17) 0.0284(9) Uani 1 1 d . . . H909 H 1.0044 -0.0844 0.4166 0.043 Uiso 1 1 calc R . . O10 O 0.81426(17) -0.21868(17) 0.45117(16) 0.0250(9) Uani 1 1 d . . . H910 H 0.7945 -0.2504 0.5072 0.037 Uiso 1 1 calc R . . O11 O 0.80880(18) -0.09530(18) 0.56169(17) 0.0276(9) Uani 1 1 d . . . H911 H 0.8510 -0.0641 0.5794 0.041 Uiso 1 1 calc R . . O12 O 0.82957(17) -0.03417(18) 0.38234(17) 0.0256(9) Uani 1 1 d . . . P4 P 1.07988(8) 0.05617(8) 0.25338(8) 0.0243(4) Uani 1 1 d . . . O13 O 1.05600(18) 0.17309(18) 0.25315(17) 0.0269(9) Uani 1 1 d . . . H913 H 1.0943 0.2048 0.2043 0.040 Uiso 1 1 calc R . . O14 O 1.17371(17) 0.03453(17) 0.17804(17) 0.0274(9) Uani 1 1 d . . . H914 H 1.2074 0.0868 0.1589 0.041 Uiso 1 1 calc R . . O15 O 1.08468(18) 0.01274(17) 0.35736(17) 0.0247(9) Uani 1 1 d . . . O16 O 0.98696(17) 0.00955(17) 0.23095(17) 0.0255(9) Uani 1 1 d . . . H916 H 0.9445 -0.0093 0.2829 0.038 Uiso 1 1 calc R . . P5 P 1.25326(8) 0.27108(8) 0.04612(8) 0.0261(4) Uani 1 1 d . . . O17 O 1.14052(17) 0.28515(18) 0.09422(17) 0.0258(9) Uani 1 1 d . . . O18 O 1.26961(19) 0.28437(18) -0.06263(17) 0.0320(10) Uani 1 1 d . . . H918 H 1.2798 0.3453 -0.0858 0.048 Uiso 1 1 calc R . . O19 O 1.31813(17) 0.35160(18) 0.06796(18) 0.0307(9) Uani 1 1 d U . . H919 H 1.3642 0.3221 0.0954 0.046 Uiso 1 1 calc RD . . O20 O 1.29719(18) 0.16460(18) 0.08398(19) 0.0316(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O101 0.0217(14) 0.0442(17) 0.0448(16) -0.0237(14) -0.0107(13) 0.0118(13) N101 0.0137(15) 0.0249(18) 0.0363(18) -0.0164(16) -0.0104(15) 0.0051(14) N102 0.0243(17) 0.0295(19) 0.0242(18) -0.0033(16) -0.0075(15) 0.0017(16) N103 0.0287(18) 0.0245(18) 0.0236(18) -0.0070(16) -0.0001(16) 0.0006(16) C101 0.052(3) 0.029(2) 0.057(3) -0.025(2) -0.030(2) 0.008(2) C102 0.028(2) 0.024(2) 0.022(2) -0.004(2) -0.0014(19) -0.0010(19) C103 0.028(2) 0.024(2) 0.037(2) -0.006(2) -0.001(2) -0.0092(19) C104 0.023(2) 0.030(2) 0.028(2) -0.006(2) -0.0077(19) -0.0059(19) C105 0.030(2) 0.033(2) 0.028(2) 0.000(2) -0.011(2) -0.0086(19) C106 0.023(2) 0.031(2) 0.017(2) -0.0045(19) -0.0029(18) -0.0050(19) C107 0.026(2) 0.026(2) 0.024(2) -0.007(2) -0.004(2) -0.0006(19) C108 0.027(2) 0.026(2) 0.016(2) -0.0030(19) -0.0023(19) -0.0071(18) C109 0.030(2) 0.031(2) 0.021(2) -0.002(2) -0.0071(19) -0.0129(19) C110 0.028(2) 0.025(2) 0.035(2) 0.000(2) 0.001(2) -0.0067(19) C111 0.038(2) 0.032(2) 0.026(2) -0.007(2) -0.002(2) -0.015(2) C112 0.033(2) 0.030(2) 0.028(2) -0.007(2) -0.006(2) -0.004(2) C113 0.028(2) 0.027(2) 0.023(2) -0.001(2) 0.001(2) -0.0079(19) O201 0.0299(15) 0.0371(17) 0.0411(16) -0.0182(14) -0.0139(13) 0.0053(13) N201 0.0310(18) 0.0200(17) 0.0114(16) -0.0049(15) 0.0017(15) -0.0046(15) N202 0.0267(17) 0.0223(18) 0.0357(19) -0.0052(16) -0.0177(15) 0.0027(15) N203 0.0180(16) 0.0264(19) 0.0323(19) -0.0014(17) -0.0041(16) -0.0030(15) C201 0.043(3) 0.031(2) 0.026(2) -0.005(2) -0.001(2) 0.002(2) C202 0.029(2) 0.020(2) 0.025(2) -0.004(2) -0.0079(19) 0.0034(19) C203 0.036(2) 0.026(2) 0.024(2) -0.0099(19) -0.0090(19) -0.0129(18) C204 0.027(2) 0.033(2) 0.023(2) -0.002(2) -0.0044(19) -0.0130(19) C205 0.027(2) 0.021(2) 0.031(2) -0.0064(19) -0.0141(19) -0.0075(18) C206 0.0145(19) 0.020(2) 0.024(2) 0.0066(19) -0.0053(18) -0.0026(17) C207 0.037(2) 0.023(2) 0.021(2) 0.005(2) -0.0063(19) -0.0140(19) C208 0.036(2) 0.022(2) 0.022(2) -0.0027(19) -0.0033(19) -0.0140(18) C209 0.029(2) 0.026(2) 0.023(2) 0.001(2) -0.0074(19) -0.0084(19) C210 0.038(2) 0.026(2) 0.032(2) -0.004(2) -0.007(2) -0.009(2) C211 0.039(2) 0.030(2) 0.028(2) -0.013(2) -0.005(2) -0.010(2) C212 0.031(2) 0.045(3) 0.032(2) -0.009(2) -0.005(2) -0.017(2) C213 0.035(2) 0.021(2) 0.034(2) -0.003(2) -0.003(2) -0.0064(19) O301 0.0197(13) 0.0349(16) 0.0403(16) -0.0177(14) -0.0076(13) 0.0046(13) N301 0.0259(17) 0.0278(18) 0.0195(17) -0.0025(16) -0.0037(15) -0.0055(15) N303 0.0171(16) 0.0284(19) 0.0245(18) -0.0027(16) -0.0050(15) 0.0019(15) C301 0.041(2) 0.028(2) 0.040(3) -0.009(2) -0.009(2) -0.007(2) C302 0.030(2) 0.020(2) 0.018(2) 0.0020(19) -0.0074(19) -0.0013(19) C303 0.036(2) 0.020(2) 0.022(2) -0.0042(19) -0.0073(19) -0.0037(19) C304 0.047(2) 0.025(2) 0.020(2) -0.008(2) -0.001(2) -0.013(2) C305 0.024(2) 0.027(2) 0.025(2) 0.012(2) -0.0091(18) -0.0170(18) C306 0.025(2) 0.024(2) 0.016(2) 0.0046(19) 0.0048(19) -0.0072(19) C307 0.035(2) 0.017(2) 0.023(2) -0.0100(18) -0.0056(19) -0.0049(19) C308 0.018(2) 0.027(2) 0.020(2) -0.0079(19) 0.0013(18) 0.0002(18) C309 0.026(2) 0.027(2) 0.033(2) -0.009(2) -0.0143(19) -0.0048(18) C310 0.026(2) 0.017(2) 0.032(2) 0.003(2) -0.003(2) 0.0035(19) C311 0.031(2) 0.025(2) 0.031(2) -0.008(2) -0.012(2) -0.0023(19) C312 0.028(2) 0.030(2) 0.025(2) -0.004(2) -0.002(2) -0.003(2) C313 0.019(2) 0.014(2) 0.036(2) -0.002(2) 0.008(2) -0.0064(17) N302 0.0195(16) 0.0309(19) 0.0190(17) -0.0005(16) -0.0061(15) -0.0017(15) P1 0.0254(6) 0.0242(6) 0.0271(6) -0.0031(5) -0.0056(5) -0.0050(5) O1 0.0179(13) 0.0281(15) 0.0388(16) 0.0082(14) -0.0043(13) -0.0033(12) O2 0.0372(15) 0.0242(14) 0.0240(15) -0.0028(13) 0.0075(13) -0.0159(12) O3 0.0243(14) 0.0275(15) 0.0261(14) -0.0105(13) -0.0043(12) -0.0013(12) O4 0.0185(13) 0.0323(15) 0.0252(14) 0.0043(13) -0.0044(12) -0.0037(12) P2 0.0244(6) 0.0257(6) 0.0232(6) -0.0040(5) -0.0017(5) -0.0035(5) O5 0.0216(13) 0.0273(15) 0.0292(15) -0.0068(13) -0.0034(13) -0.0016(12) O6 0.0261(14) 0.0271(15) 0.0228(14) 0.0021(13) -0.0064(12) -0.0046(12) O7 0.0241(14) 0.0530(18) 0.0229(14) -0.0021(14) -0.0082(12) -0.0135(13) O8 0.0328(15) 0.0240(15) 0.0255(15) -0.0029(13) 0.0029(13) -0.0023(13) P3 0.0255(6) 0.0262(6) 0.0233(6) -0.0011(5) -0.0017(5) -0.0038(5) O9 0.0186(13) 0.0240(15) 0.0350(16) 0.0062(14) 0.0024(13) -0.0041(12) O10 0.0361(14) 0.0237(14) 0.0166(14) -0.0019(12) -0.0045(12) -0.0145(12) O11 0.0281(14) 0.0314(15) 0.0254(14) -0.0035(13) -0.0063(12) -0.0125(12) O12 0.0227(14) 0.0248(15) 0.0260(15) 0.0009(13) -0.0024(13) -0.0010(12) P4 0.0250(6) 0.0242(6) 0.0226(6) -0.0041(5) -0.0020(5) -0.0038(5) O13 0.0277(14) 0.0210(14) 0.0260(15) -0.0010(13) 0.0060(13) -0.0065(12) O14 0.0299(14) 0.0147(14) 0.0356(16) -0.0065(13) 0.0006(13) -0.0058(12) O15 0.0322(14) 0.0214(14) 0.0186(14) 0.0046(13) -0.0045(12) -0.0077(12) O16 0.0223(13) 0.0333(15) 0.0201(14) -0.0007(13) -0.0013(12) -0.0116(12) P5 0.0275(6) 0.0276(6) 0.0221(6) -0.0007(5) -0.0031(5) -0.0077(5) O17 0.0221(14) 0.0266(15) 0.0224(14) 0.0037(13) 0.0016(13) -0.0006(12) O18 0.0492(16) 0.0249(14) 0.0230(14) -0.0004(13) -0.0062(13) -0.0176(13) O19 0.0244(13) 0.0321(15) 0.0370(15) 0.0006(14) -0.0090(13) -0.0131(12) O20 0.0281(14) 0.0187(15) 0.0455(17) 0.0028(14) -0.0100(14) 0.0009(13) _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 O101 C107 1.216(4) . ? N101 C106 1.337(4) . ? N101 C105 1.347(5) . ? N102 C106 1.383(5) . ? N102 C107 1.396(5) . ? N103 C107 1.356(5) . ? N103 C108 1.413(5) . ? C101 C102 1.496(5) . ? C102 C103 1.381(6) . ? C102 C106 1.417(5) . ? C103 C104 1.392(5) . ? C104 C105 1.343(6) . ? C108 C109 1.374(5) . ? C108 C113 1.388(6) . ? C109 C110 1.396(6) . ? C110 C111 1.382(6) . ? C111 C112 1.377(5) . ? C112 C113 1.372(6) . ? O201 C207 1.226(4) . ? N201 C206 1.351(4) . ? N201 C205 1.355(5) . ? N202 C206 1.369(5) . ? N202 C207 1.382(5) . ? N203 C207 1.370(5) . ? N203 C208 1.417(5) . ? C201 C202 1.515(5) . ? C202 C203 1.371(6) . ? C202 C206 1.400(5) . ? C203 C204 1.403(5) . ? C204 C205 1.338(5) . ? C208 C209 1.374(5) . ? C208 C213 1.386(6) . ? C209 C210 1.393(6) . ? C210 C211 1.366(6) . ? C211 C212 1.377(5) . ? C212 C213 1.387(6) . ? O301 C307 1.219(4) . ? N301 C306 1.352(4) . ? N301 C305 1.356(5) . ? N303 C307 1.346(5) . ? N303 C308 1.401(5) . ? C301 C302 1.505(5) . ? C302 C303 1.384(6) . ? C302 C306 1.401(5) . ? C303 C304 1.403(5) . ? C304 C305 1.361(5) . ? C306 N302 1.361(5) . ? C307 N302 1.417(5) . ? C308 C309 1.384(5) . ? C308 C313 1.396(6) . ? C309 C310 1.406(6) . ? C310 C311 1.368(6) . ? C311 C312 1.390(5) . ? C312 C313 1.382(6) . ? P1 O2 1.488(3) . ? P1 O4 1.508(3) . ? P1 O1 1.567(3) . ? P1 O3 1.597(3) . ? P2 O5 1.502(2) . ? P2 O6 1.517(3) . ? P2 O7 1.554(3) . ? P2 O8 1.579(3) . ? P3 O12 1.504(3) . ? P3 O10 1.525(3) . ? P3 O9 1.554(3) . ? P3 O11 1.557(3) . ? P4 O14 1.486(2) . ? P4 O15 1.527(3) . ? P4 O16 1.561(3) . ? P4 O13 1.569(3) . ? P5 O17 1.503(2) . ? P5 O18 1.511(3) . ? P5 O20 1.551(3) . ? P5 O19 1.562(3) . ? 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 C106 N101 C105 122.4(3) . . ? C106 N102 C107 124.4(3) . . ? C107 N103 C108 127.2(3) . . ? C103 C102 C106 116.3(3) . . ? C103 C102 C101 123.1(4) . . ? C106 C102 C101 120.5(4) . . ? C102 C103 C104 122.1(4) . . ? C105 C104 C103 118.5(4) . . ? C104 C105 N101 120.7(3) . . ? N101 C106 N102 119.2(3) . . ? N101 C106 C102 119.9(4) . . ? N102 C106 C102 121.0(3) . . ? O101 C107 N103 125.4(4) . . ? O101 C107 N102 122.2(4) . . ? N103 C107 N102 112.4(3) . . ? C109 C108 C113 120.2(4) . . ? C109 C108 N103 123.4(4) . . ? C113 C108 N103 116.4(3) . . ? C108 C109 C110 119.1(4) . . ? C111 C110 C109 120.8(3) . . ? C112 C111 C110 118.8(4) . . ? C113 C112 C111 121.2(4) . . ? C112 C113 C108 119.7(3) . . ? C206 N201 C205 124.1(3) . . ? C206 N202 C207 126.3(3) . . ? C207 N203 C208 128.3(3) . . ? C203 C202 C206 118.0(3) . . ? C203 C202 C201 122.3(4) . . ? C206 C202 C201 119.7(4) . . ? C202 C203 C204 121.2(4) . . ? C205 C204 C203 119.7(4) . . ? C204 C205 N201 118.7(3) . . ? N201 C206 N202 118.4(3) . . ? N201 C206 C202 118.3(4) . . ? N202 C206 C202 123.3(3) . . ? O201 C207 N203 124.3(4) . . ? O201 C207 N202 122.6(4) . . ? N203 C207 N202 113.0(3) . . ? C209 C208 C213 121.5(4) . . ? C209 C208 N203 123.2(4) . . ? C213 C208 N203 115.2(3) . . ? C208 C209 C210 117.8(4) . . ? C211 C210 C209 122.1(3) . . ? C210 C211 C212 118.9(4) . . ? C211 C212 C213 120.8(4) . . ? C208 C213 C212 118.9(3) . . ? C306 N301 C305 123.9(3) . . ? C307 N303 C308 126.6(3) . . ? C303 C302 C306 117.5(3) . . ? C303 C302 C301 121.3(3) . . ? C306 C302 C301 121.2(4) . . ? C302 C303 C304 121.9(4) . . ? C305 C304 C303 118.7(4) . . ? N301 C305 C304 119.1(3) . . ? N301 C306 N302 118.9(3) . . ? N301 C306 C302 118.9(4) . . ? N302 C306 C302 122.3(3) . . ? O301 C307 N303 128.0(4) . . ? O301 C307 N302 121.4(4) . . ? N303 C307 N302 110.6(3) . . ? C309 C308 C313 119.8(4) . . ? C309 C308 N303 124.3(4) . . ? C313 C308 N303 115.9(3) . . ? C308 C309 C310 118.6(4) . . ? C311 C310 C309 121.8(3) . . ? C310 C311 C312 119.1(4) . . ? C313 C312 C311 120.3(4) . . ? C312 C313 C308 120.4(3) . . ? C306 N302 C307 125.7(3) . . ? O2 P1 O4 116.19(16) . . ? O2 P1 O1 107.71(15) . . ? O4 P1 O1 108.94(13) . . ? O2 P1 O3 109.47(14) . . ? O4 P1 O3 107.02(14) . . ? O1 P1 O3 107.18(15) . . ? O5 P2 O6 115.75(14) . . ? O5 P2 O7 107.83(15) . . ? O6 P2 O7 109.83(14) . . ? O5 P2 O8 109.17(14) . . ? O6 P2 O8 106.32(15) . . ? O7 P2 O8 107.67(15) . . ? O12 P3 O10 112.20(16) . . ? O12 P3 O9 111.65(13) . . ? O10 P3 O9 107.25(14) . . ? O12 P3 O11 111.58(14) . . ? O10 P3 O11 106.33(13) . . ? O9 P3 O11 107.53(15) . . ? O14 P4 O15 115.74(14) . . ? O14 P4 O16 107.55(15) . . ? O15 P4 O16 107.26(14) . . ? O14 P4 O13 111.44(13) . . ? O15 P4 O13 105.20(15) . . ? O16 P4 O13 109.48(14) . . ? O17 P5 O18 111.44(15) . . ? O17 P5 O20 109.98(13) . . ? O18 P5 O20 109.94(15) . . ? O17 P5 O19 111.28(15) . . ? O18 P5 O19 106.18(14) . . ? O20 P5 O19 107.90(15) . . ? 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 N101 H101 O101 0.88 1.94 2.604(5) 130.7 . O13 H913 O17 0.84 1.77 2.589(3) 163.7 . O14 H914 O20 0.84 1.71 2.506(3) 156.9 . O16 H916 O12 0.84 1.84 2.667(3) 166.9 . N102 H102 O12 0.88 2.11 2.928(4) 153.3 . N103 H503 O12 0.88 2.04 2.880(4) 158.1 . N201 H201 O201 0.88 1.94 2.621(4) 133.2 . N201 H201 O13 0.88 2.25 2.926(4) 133.3 . N303 H703 O17 0.88 1.95 2.777(4) 155.7 . N302 H302 O17 0.88 2.03 2.843(4) 152.2 . O1 H901 O6 0.84 1.78 2.616(3) 171.4 . O7 H907 O4 0.84 1.80 2.628(3) 169.9 . O8 H8 O11 0.84 1.88 2.705(3) 166.8 . O9 H909 O15 0.84 1.74 2.572(3) 170.2 . O10 H910 O5 0.84 1.69 2.477(3) 155.8 . N301 H301 O301 0.88 1.92 2.605(4) 133.6 . N101 H101 O8 0.88 2.30 2.965(4) 132.2 2_656 N202 H202 O4 0.88 1.98 2.797(4) 154.5 2_656 N203 H603 O4 0.88 2.00 2.822(4) 154.4 2_656 N301 H301 O3 0.88 2.43 3.096(4) 133.1 2_656 O3 H3 O19 0.84 1.89 2.711(3) 166.7 1_446 O11 H911 O15 0.84 1.66 2.477(4) 165.0 2_756 O18 H918 O2 0.84 1.92 2.459(3) 121.0 1_664 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.590 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.111 data_2005sot1027 _database_code_depnum_ccdc_archive 'CCDC 603103' _chemical_compound_source 'Suad Rashdan' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 B F4 N3 O S' _chemical_formula_weight 335.13 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.2690(6) _cell_length_b 22.1000(15) _cell_length_c 7.1372(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.363(4) _cell_angle_gamma 90.00 _cell_volume 1449.96(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3235 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9505 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 10405 reflections reduced R(int) from 0.0749 to 0.0551 Ratio of minimum to maximum apparent transmission: 0.612466 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18054 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3311 _reflns_number_gt 2160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0560P)^2^+1.1188P] 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 3311 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 O1 O 0.2452(2) 0.33238(10) -0.0837(4) 0.0317(5) Uani 1 1 d . . . H99 H 0.262(4) 0.3205(17) 0.027(6) 0.061(13) Uiso 1 1 d . . . H98 H 0.242(4) 0.301(2) -0.154(6) 0.074(14) Uiso 1 1 d . . . C1 C -0.2339(3) 0.39166(13) 0.2903(4) 0.0296(6) Uani 1 1 d . . . H1 H -0.1856 0.3548 0.3092 0.036 Uiso 1 1 calc R . . C2 C -0.3803(3) 0.39399(13) 0.2882(4) 0.0326(7) Uani 1 1 d . . . H2 H -0.4331 0.3590 0.3042 0.039 Uiso 1 1 calc R . . C3 C -0.4499(3) 0.44956(13) 0.2618(4) 0.0330(7) Uani 1 1 d . . . H3 H -0.5502 0.4518 0.2606 0.040 Uiso 1 1 calc R . . C4 C -0.3722(3) 0.50111(13) 0.2375(4) 0.0311(6) Uani 1 1 d . . . H4 H -0.4192 0.5382 0.2201 0.037 Uiso 1 1 calc R . . C5 C -0.2209(3) 0.49719(12) 0.2393(4) 0.0256(6) Uani 1 1 d . . . C6 C 0.0058(3) 0.55726(12) 0.2106(4) 0.0246(6) Uani 1 1 d . . . C7 C 0.1609(3) 0.64632(12) 0.1454(4) 0.0252(6) Uani 1 1 d . . . C8 C 0.1417(3) 0.70170(13) 0.0501(4) 0.0273(6) Uani 1 1 d . . . H8 H 0.0486 0.7149 0.0041 0.033 Uiso 1 1 calc R . . C9 C 0.2610(3) 0.73653(13) 0.0246(4) 0.0292(6) Uani 1 1 d . . . H9 H 0.2483 0.7728 -0.0414 0.035 Uiso 1 1 calc R . . C10 C 0.3995(3) 0.71782(13) 0.0967(4) 0.0305(6) Uani 1 1 d . . . H10 H 0.4797 0.7415 0.0794 0.037 Uiso 1 1 calc R . . C11 C 0.4182(3) 0.66408(13) 0.1942(4) 0.0295(6) Uani 1 1 d . . . H11 H 0.5113 0.6519 0.2440 0.035 Uiso 1 1 calc R . . C12 C 0.2996(3) 0.62773(13) 0.2190(4) 0.0271(6) Uani 1 1 d . . . H12 H 0.3131 0.5913 0.2843 0.033 Uiso 1 1 calc R . . N1 N -0.1573(2) 0.44286(10) 0.2649(3) 0.0258(5) Uani 1 1 d . . . H1A H -0.0647 0.4403 0.2653 0.031 Uiso 1 1 calc R . . N2 N -0.1424(2) 0.54845(10) 0.2143(3) 0.0283(5) Uani 1 1 d . . . H2A H -0.1938 0.5809 0.1980 0.034 Uiso 1 1 calc R . . N3 N 0.0304(2) 0.61463(10) 0.1648(3) 0.0282(5) Uani 1 1 d . . . H3A H -0.0470 0.6363 0.1432 0.034 Uiso 1 1 calc R . . S1 S 0.12878(7) 0.50242(3) 0.25789(10) 0.0293(2) Uani 1 1 d . . . B1 B 0.2061(3) 0.33593(15) 0.4079(5) 0.0305(7) Uani 1 1 d . . . F1 F 0.29302(19) 0.30227(8) 0.3002(2) 0.0467(5) Uani 1 1 d . . . F2 F 0.1607(2) 0.29848(9) 0.5444(3) 0.0585(6) Uani 1 1 d . . . F3 F 0.08646(18) 0.35694(8) 0.2904(3) 0.0442(5) Uani 1 1 d . . . F4 F 0.28656(17) 0.38353(8) 0.4935(2) 0.0387(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0280(11) 0.0322(13) 0.0346(12) 0.0035(11) 0.0032(9) 0.0040(9) C1 0.0353(16) 0.0252(16) 0.0282(15) -0.0016(12) 0.0032(11) -0.0012(12) C2 0.0325(16) 0.0306(17) 0.0347(16) 0.0000(13) 0.0044(12) -0.0061(13) C3 0.0247(14) 0.0353(18) 0.0394(16) -0.0011(13) 0.0050(12) -0.0047(13) C4 0.0240(14) 0.0304(16) 0.0386(16) -0.0001(13) 0.0032(11) 0.0014(12) C5 0.0245(13) 0.0259(15) 0.0259(13) -0.0023(12) 0.0018(10) -0.0033(12) C6 0.0220(13) 0.0258(15) 0.0254(13) -0.0020(12) 0.0009(10) 0.0006(11) C7 0.0235(14) 0.0266(15) 0.0255(13) -0.0049(12) 0.0028(10) -0.0019(11) C8 0.0215(13) 0.0291(16) 0.0303(15) -0.0017(12) -0.0002(11) 0.0023(11) C9 0.0323(15) 0.0263(16) 0.0289(15) -0.0004(12) 0.0038(11) -0.0015(12) C10 0.0233(14) 0.0319(17) 0.0362(16) -0.0026(13) 0.0045(11) -0.0057(12) C11 0.0197(13) 0.0331(17) 0.0350(15) -0.0023(13) 0.0004(11) 0.0015(12) C12 0.0256(14) 0.0253(15) 0.0298(14) 0.0006(12) 0.0008(11) 0.0006(11) N1 0.0214(11) 0.0264(13) 0.0294(12) -0.0014(10) 0.0031(9) -0.0001(10) N2 0.0227(11) 0.0242(13) 0.0376(13) 0.0010(10) 0.0030(9) 0.0015(10) N3 0.0196(11) 0.0271(13) 0.0369(13) 0.0038(10) 0.0001(9) 0.0029(9) S1 0.0232(3) 0.0255(4) 0.0387(4) 0.0008(3) 0.0020(3) 0.0024(3) B1 0.0308(17) 0.0278(18) 0.0322(17) 0.0013(14) 0.0015(13) 0.0014(14) F1 0.0462(11) 0.0536(12) 0.0390(10) -0.0080(9) -0.0002(8) 0.0214(9) F2 0.0815(15) 0.0512(13) 0.0427(11) 0.0028(9) 0.0080(10) -0.0203(11) F3 0.0318(9) 0.0383(11) 0.0583(11) -0.0074(9) -0.0109(8) 0.0072(8) F4 0.0337(9) 0.0340(10) 0.0459(10) -0.0058(8) -0.0046(7) -0.0022(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 C1 C2 1.356(4) . ? C1 N1 1.360(3) . ? C2 C3 1.389(4) . ? C3 C4 1.371(4) . ? C4 C5 1.404(4) . ? C5 N1 1.339(3) . ? C5 N2 1.370(3) . ? C6 N3 1.336(3) . ? C6 N2 1.391(3) . ? C6 S1 1.668(3) . ? C7 C12 1.387(4) . ? C7 C8 1.400(4) . ? C7 N3 1.420(3) . ? C8 C9 1.379(4) . ? C9 C10 1.383(4) . ? C10 C11 1.376(4) . ? C11 C12 1.392(4) . ? B1 F3 1.382(4) . ? B1 F2 1.384(4) . ? B1 F4 1.385(4) . ? B1 F1 1.397(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 120.4(3) . . ? C1 C2 C3 118.8(3) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C5 119.2(3) . . ? N1 C5 N2 121.8(2) . . ? N1 C5 C4 118.5(2) . . ? N2 C5 C4 119.6(2) . . ? N3 C6 N2 109.7(2) . . ? N3 C6 S1 127.3(2) . . ? N2 C6 S1 123.0(2) . . ? C12 C7 C8 119.8(2) . . ? C12 C7 N3 125.2(2) . . ? C8 C7 N3 114.9(2) . . ? C9 C8 C7 119.9(2) . . ? C8 C9 C10 120.4(3) . . ? C11 C10 C9 119.8(3) . . ? C10 C11 C12 120.8(3) . . ? C7 C12 C11 119.3(3) . . ? C5 N1 C1 122.4(2) . . ? C5 N2 C6 131.3(2) . . ? C6 N3 C7 131.8(2) . . ? F3 B1 F2 109.6(2) . . ? F3 B1 F4 110.9(3) . . ? F2 B1 F4 109.8(2) . . ? F3 B1 F1 108.7(2) . . ? F2 B1 F1 108.5(3) . . ? F4 B1 F1 109.3(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 O1 H99 F1 0.83(4) 1.98(4) 2.800(3) 173(4) . O1 H98 F2 0.85(5) 2.19(4) 2.772(3) 126(4) 1_554 O1 H98 F1 0.85(5) 2.37(5) 3.135(3) 150(4) 4_565 N1 H1A S1 0.86 2.27 2.967(2) 138.8 . N1 H1A F3 0.86 2.31 2.939(3) 130.5 . N3 H3A O1 0.86 1.96 2.803(3) 166.8 3_565 N2 H2A F4 0.86 2.59 3.018(3) 112.2 3_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.350 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.066 data_2006sot0564 _database_code_depnum_ccdc_archive 'CCDC 605518' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 F3 N3 O2 S' _chemical_formula_weight 343.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.24050(10) _cell_length_b 16.2008(4) _cell_length_c 17.6222(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1496.13(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2007 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9395 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 12633 reflections reduced R(int) from 0.0818 to 0.0475 Ratio of minimum to maximum apparent transmission: 0.718595 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14531 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3408 _reflns_number_gt 3033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0526P)^2^+0.1240P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(8) _refine_ls_number_reflns 3408 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.16928(10) 0.30235(3) 0.92946(3) 0.02010(14) Uani 1 1 d . . . N1 N 0.1624(3) 0.35488(10) 1.09095(9) 0.0181(4) Uani 1 1 d . . . H99 H 0.232(5) 0.3234(17) 1.0540(16) 0.043(8) Uiso 1 1 d . . . N2 N -0.1458(3) 0.40708(10) 1.00485(9) 0.0189(4) Uani 1 1 d . . . H2 H -0.2834 0.4380 1.0016 0.023 Uiso 1 1 calc R . . N3 N -0.2049(4) 0.39881(11) 0.87882(10) 0.0212(4) Uani 1 1 d . . . H3 H -0.3310 0.4332 0.8884 0.025 Uiso 1 1 calc R . . C1 C 0.2687(4) 0.34994(12) 1.16106(11) 0.0203(5) Uani 1 1 d . . . H1 H 0.4157 0.3167 1.1688 0.024 Uiso 1 1 calc R . . C2 C 0.1666(4) 0.39205(13) 1.22015(12) 0.0250(5) Uani 1 1 d . . . H2A H 0.2413 0.3890 1.2692 0.030 Uiso 1 1 calc R . . C3 C -0.0519(4) 0.44019(13) 1.20737(12) 0.0245(5) Uani 1 1 d . . . H3A H -0.1291 0.4690 1.2483 0.029 Uiso 1 1 calc R . . C4 C -0.1543(4) 0.44587(12) 1.13594(12) 0.0207(4) Uani 1 1 d . . . H4 H -0.2994 0.4797 1.1270 0.025 Uiso 1 1 calc R . . C5 C -0.0435(4) 0.40146(11) 1.07628(11) 0.0171(4) Uani 1 1 d . . . C6 C -0.0685(4) 0.37217(12) 0.93716(11) 0.0170(4) Uani 1 1 d . . . C7 C -0.1622(4) 0.37570(12) 0.80101(11) 0.0190(4) Uani 1 1 d . . . C8 C 0.0476(4) 0.40676(14) 0.76293(12) 0.0231(5) Uani 1 1 d . . . H8 H 0.1680 0.4405 0.7887 0.028 Uiso 1 1 calc R . . C9 C 0.0804(4) 0.38815(14) 0.68656(12) 0.0253(5) Uani 1 1 d . . . H9 H 0.2238 0.4090 0.6597 0.030 Uiso 1 1 calc R . . C10 C -0.0975(4) 0.33895(14) 0.64969(12) 0.0258(5) Uani 1 1 d . . . H10 H -0.0737 0.3256 0.5977 0.031 Uiso 1 1 calc R . . C11 C -0.3084(4) 0.30915(13) 0.68775(12) 0.0250(5) Uani 1 1 d . . . H11 H -0.4302 0.2759 0.6620 0.030 Uiso 1 1 calc R . . C12 C -0.3413(4) 0.32823(13) 0.76452(12) 0.0222(4) Uani 1 1 d . . . H12 H -0.4865 0.3085 0.7912 0.027 Uiso 1 1 calc R . . O1 O -0.5730(3) 0.50454(9) 1.01214(8) 0.0244(4) Uani 1 1 d . . . O2 O -0.5792(3) 0.51988(10) 0.88553(8) 0.0270(4) Uani 1 1 d . . . F1 F -0.9872(3) 0.59976(9) 1.02049(8) 0.0450(4) Uani 1 1 d . . . F2 F -0.7218(3) 0.67887(8) 0.96507(10) 0.0483(4) Uani 1 1 d . . . F3 F -0.9963(3) 0.61311(11) 0.90011(8) 0.0520(5) Uani 1 1 d . . . C13 C -0.6459(4) 0.53610(12) 0.95122(12) 0.0195(4) Uani 1 1 d . . . C14 C -0.8418(5) 0.60665(13) 0.95942(12) 0.0251(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0215(3) 0.0227(2) 0.0161(3) -0.0011(2) 0.0001(2) 0.0040(2) N1 0.0202(9) 0.0189(8) 0.0151(8) -0.0027(7) -0.0009(8) -0.0005(8) N2 0.0184(8) 0.0221(8) 0.0161(9) -0.0012(7) 0.0002(8) 0.0025(8) N3 0.0225(10) 0.0264(9) 0.0148(8) -0.0010(7) 0.0006(8) 0.0083(8) C1 0.0222(11) 0.0219(10) 0.0168(11) 0.0019(8) -0.0027(9) 0.0000(9) C2 0.0306(12) 0.0270(11) 0.0174(10) -0.0012(8) -0.0033(11) 0.0015(10) C3 0.0318(12) 0.0237(11) 0.0179(11) -0.0030(9) 0.0007(10) 0.0018(10) C4 0.0229(10) 0.0200(10) 0.0194(11) -0.0010(8) 0.0013(10) 0.0026(9) C5 0.0183(10) 0.0180(10) 0.0150(10) 0.0019(8) 0.0002(9) -0.0032(8) C6 0.0173(9) 0.0180(9) 0.0158(10) -0.0004(8) 0.0009(9) -0.0037(8) C7 0.0218(10) 0.0220(10) 0.0131(9) 0.0002(8) -0.0013(9) 0.0082(9) C8 0.0212(11) 0.0278(12) 0.0204(11) 0.0003(9) -0.0020(10) -0.0011(9) C9 0.0256(12) 0.0321(12) 0.0183(11) 0.0047(9) 0.0006(10) 0.0048(10) C10 0.0332(12) 0.0290(12) 0.0150(10) -0.0007(9) 0.0013(10) 0.0095(10) C11 0.0289(12) 0.0263(11) 0.0197(11) -0.0046(9) -0.0033(10) 0.0014(10) C12 0.0229(10) 0.0258(10) 0.0180(10) 0.0010(8) 0.0013(10) 0.0046(9) O1 0.0264(8) 0.0314(8) 0.0155(8) 0.0015(6) -0.0008(7) 0.0053(7) O2 0.0301(9) 0.0344(9) 0.0164(8) -0.0005(7) 0.0022(7) 0.0083(7) F1 0.0493(9) 0.0480(9) 0.0377(9) 0.0096(7) 0.0221(8) 0.0237(8) F2 0.0545(9) 0.0229(7) 0.0675(11) 0.0042(7) 0.0001(9) 0.0040(7) F3 0.0442(9) 0.0797(12) 0.0321(8) -0.0101(8) -0.0155(8) 0.0330(9) C13 0.0180(10) 0.0215(10) 0.0190(11) -0.0003(8) -0.0002(9) -0.0027(9) C14 0.0270(11) 0.0309(11) 0.0175(10) 0.0028(9) 0.0022(10) 0.0035(10) _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 C6 1.688(2) . ? N1 C5 1.342(3) . ? N1 C1 1.358(3) . ? N2 C5 1.371(3) . ? N2 C6 1.381(3) . ? N3 C6 1.324(3) . ? N3 C7 1.439(3) . ? C1 C2 1.355(3) . ? C2 C3 1.403(3) . ? C3 C4 1.371(3) . ? C4 C5 1.400(3) . ? C7 C12 1.373(3) . ? C7 C8 1.383(3) . ? C8 C9 1.390(3) . ? C9 C10 1.388(3) . ? C10 C11 1.380(3) . ? C11 C12 1.398(3) . ? O1 C13 1.249(2) . ? O2 C13 1.237(3) . ? F1 C14 1.324(3) . ? F2 C14 1.332(3) . ? F3 C14 1.326(3) . ? C13 C14 1.543(3) . ? 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 C5 N1 C1 122.57(18) . . ? C5 N2 C6 130.61(18) . . ? C6 N3 C7 124.81(18) . . ? C2 C1 N1 120.52(19) . . ? C1 C2 C3 118.6(2) . . ? C4 C3 C2 120.3(2) . . ? C3 C4 C5 119.5(2) . . ? N1 C5 N2 121.91(18) . . ? N1 C5 C4 118.55(19) . . ? N2 C5 C4 119.53(18) . . ? N3 C6 N2 112.25(17) . . ? N3 C6 S1 123.67(15) . . ? N2 C6 S1 124.08(16) . . ? C12 C7 C8 121.32(19) . . ? C12 C7 N3 119.1(2) . . ? C8 C7 N3 119.4(2) . . ? C7 C8 C9 119.3(2) . . ? C10 C9 C8 119.7(2) . . ? C11 C10 C9 120.7(2) . . ? C10 C11 C12 119.5(2) . . ? C7 C12 C11 119.5(2) . . ? O2 C13 O1 129.1(2) . . ? O2 C13 C14 115.65(18) . . ? O1 C13 C14 115.23(18) . . ? F1 C14 F3 107.20(18) . . ? F1 C14 F2 106.57(19) . . ? F3 C14 F2 106.13(18) . . ? F1 C14 C13 113.38(17) . . ? F3 C14 C13 113.01(17) . . ? F2 C14 C13 110.10(18) . . ? 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 H99 S1 0.91(3) 2.24(3) 2.9705(18) 137(2) . N2 H2 O1 0.88 1.87 2.742(2) 170.6 . N3 H3 O2 0.88 1.92 2.776(2) 165.7 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.175 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.050