 
data_02sot029 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H31 F6 N5 O4 P' 
_chemical_formula_weight          574.49 
 
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' 
 'P'  'P'   0.1023   0.0942 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pbca
 
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' 
 '-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                    16.1973(5) 
_cell_length_b                    9.3378(2) 
_cell_length_c                    34.0104(12) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      5144.0(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     13854 
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       25.35
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.484 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              2392 
_exptl_absorpt_coefficient_mu     0.190 
_exptl_absorpt_correction_type    multiscans 
_exptl_absorpt_correction_T_min   0.9813 
_exptl_absorpt_correction_T_max   0.9962 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details 
; 
 ? 
; 
 
_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   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             18704 
_diffrn_reflns_av_R_equivalents   0.1556 
_diffrn_reflns_av_sigmaI/netI     0.1655 
_diffrn_reflns_limit_h_min        -19 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -40 
_diffrn_reflns_limit_l_max        39 
_diffrn_reflns_theta_min          3.09 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              4519 
_reflns_number_gt                 2080 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0796P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4519 
_refine_ls_number_parameters      361 
_refine_ls_number_restraints      6 
_refine_ls_R_factor_all           0.1733 
_refine_ls_R_factor_gt            0.0651 
_refine_ls_wR_factor_ref          0.1760 
_refine_ls_wR_factor_gt           0.1374 
_refine_ls_goodness_of_fit_ref    0.927 
_refine_ls_restrained_S_all       0.926 
_refine_ls_shift/su_max           0.046 
_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 
O2W O 0.1612(2) 0.6122(4) 0.65744(12) 0.0444(10) Uani 1 1 d D . . 
O1W O -0.0753(3) 0.3713(5) 0.75829(13) 0.0640(12) Uani 1 1 d D . . 
H1W H -0.1035(19) 0.401(5) 0.7369(7) 0.030(16) Uiso 1 1 d D . . 
H4W H 0.2120(14) 0.617(6) 0.6681(15) 0.09(2) Uiso 1 1 d D . . 
H3W H 0.145(4) 0.548(9) 0.639(3) 0.25(6) Uiso 1 1 d D . . 
H2W H -0.026(5) 0.327(17) 0.7580(12) 0.45(12) Uiso 1 1 d D . . 
P1 P 0.13089(8) 0.24615(15) 0.70913(4) 0.0332(4) Uani 1 1 d . . . 
F1 F 0.07521(15) 0.3905(3) 0.72327(8) 0.0366(7) Uani 1 1 d . . . 
O2 O 0.45613(18) -0.0345(3) 0.88354(8) 0.0278(8) Uani 1 1 d . . . 
O1 O 0.44618(18) -0.0482(4) 1.03206(9) 0.0311(9) Uani 1 1 d . . . 
N3 N 0.3836(2) -0.0433(4) 0.95696(10) 0.0180(9) Uani 1 1 d . . . 
H3 H 0.4379 -0.0418 0.9578 0.022 Uiso 1 1 calc R . . 
F4 F 0.18974(16) 0.1022(3) 0.69558(8) 0.0404(8) Uani 1 1 d . . . 
F2 F 0.1176(2) 0.1698(3) 0.75302(8) 0.0577(9) Uani 1 1 d . . . 
N2 N 0.3211(2) -0.0729(4) 1.05956(10) 0.0222(9) Uani 1 1 d . . . 
H2 H 0.2681 -0.0885 1.0557 0.027 Uiso 1 1 calc R . . 
F6 F 0.04806(17) 0.1652(3) 0.69231(9) 0.0523(9) Uani 1 1 d . . . 
F5 F 0.1461(2) 0.3212(3) 0.66517(8) 0.0625(10) Uani 1 1 d . . . 
C4 C 0.3330(2) -0.0507(4) 0.98906(12) 0.0187(11) Uani 1 1 d . . . 
C17 C 0.1821(2) -0.0372(5) 0.90691(12) 0.0189(11) Uani 1 1 d . . . 
C7 C 0.3373(2) -0.0386(5) 0.92354(12) 0.0164(11) Uani 1 1 d . . . 
N4 N 0.3322(2) -0.0304(4) 0.85288(11) 0.0291(10) Uani 1 1 d . . . 
H4 H 0.2787 -0.0425 0.8559 0.035 Uiso 1 1 calc R . . 
C8 C 0.3801(3) -0.0342(5) 0.88505(13) 0.0218(11) Uani 1 1 d . . . 
C11 C 0.1754(3) -0.0552(5) 1.00043(12) 0.0206(11) Uani 1 1 d . . . 
C3 C 0.3713(3) -0.0570(5) 1.02840(13) 0.0218(11) Uani 1 1 d . . . 
C6 C 0.2546(3) -0.0442(4) 0.93415(13) 0.0200(11) Uani 1 1 d . . . 
F3 F 0.21575(16) 0.3265(3) 0.72641(10) 0.0585(10) Uani 1 1 d . . . 
N1 N 0.3928(2) 0.1086(4) 1.15131(11) 0.0251(10) Uani 1 1 d . . . 
H1A H 0.3716 0.0480 1.1697 0.038 Uiso 1 1 calc R . . 
H1B H 0.3870 0.2006 1.1597 0.038 Uiso 1 1 calc R . . 
H1C H 0.4473 0.0888 1.1477 0.038 Uiso 1 1 calc R . . 
C2 C 0.3524(3) -0.0649(5) 1.09933(13) 0.0257(12) Uani 1 1 d . . . 
H2A H 0.4103 -0.0987 1.1001 0.031 Uiso 1 1 calc R . . 
H2B H 0.3192 -0.1272 1.1168 0.031 Uiso 1 1 calc R . . 
C22 C 0.1629(3) 0.0885(5) 0.88723(13) 0.0257(12) Uani 1 1 d . . . 
H22 H 0.1934 0.1728 0.8930 0.031 Uiso 1 1 calc R . . 
C21 C 0.1009(3) 0.0948(5) 0.85966(14) 0.0272(12) Uani 1 1 d . . . 
H21 H 0.0901 0.1815 0.8460 0.033 Uiso 1 1 calc R . . 
C5 C 0.2510(3) -0.0519(4) 0.97584(13) 0.0193(11) Uani 1 1 d . . . 
C14 C 0.0359(3) -0.0574(6) 1.04817(15) 0.0309(13) Uani 1 1 d . . . 
H14 H -0.0112 -0.0599 1.0648 0.037 Uiso 1 1 calc R . . 
C9 C 0.3639(3) -0.0072(6) 0.81313(13) 0.0344(14) Uani 1 1 d . . . 
H9A H 0.3658 -0.0990 0.7986 0.041 Uiso 1 1 calc R . . 
H9B H 0.4206 0.0325 0.8143 0.041 Uiso 1 1 calc R . . 
C13 C 0.0840(3) 0.0642(5) 1.04628(14) 0.0330(13) Uani 1 1 d . . . 
H13 H 0.0698 0.1465 1.0612 0.040 Uiso 1 1 calc R . . 
N5 N 0.3317(2) 0.1227(4) 0.75191(11) 0.0352(11) Uani 1 1 d . . . 
H5A H 0.3746 0.1856 0.7514 0.053 Uiso 1 1 calc R . . 
H5B H 0.2881 0.1602 0.7385 0.053 Uiso 1 1 calc R . . 
H5C H 0.3474 0.0389 0.7405 0.053 Uiso 1 1 calc R . . 
C20 C 0.0543(3) -0.0266(6) 0.85202(15) 0.0330(13) Uani 1 1 d . . . 
H20 H 0.0113 -0.0238 0.8330 0.040 Uiso 1 1 calc R . . 
C16 C 0.1257(3) -0.1753(5) 1.00244(13) 0.0270(12) Uani 1 1 d . . . 
H16 H 0.1394 -0.2583 0.9876 0.032 Uiso 1 1 calc R . . 
C12 C 0.1530(3) 0.0656(5) 1.02251(14) 0.0279(12) Uani 1 1 d . . . 
H12 H 0.1859 0.1497 1.0211 0.033 Uiso 1 1 calc R . . 
C19 C 0.0708(3) -0.1509(6) 0.87212(14) 0.0301(13) Uani 1 1 d . . . 
H19 H 0.0384 -0.2338 0.8673 0.036 Uiso 1 1 calc R . . 
C15 C 0.0561(3) -0.1751(6) 1.02586(14) 0.0312(13) Uani 1 1 d . . . 
H15 H 0.0217 -0.2575 1.0266 0.037 Uiso 1 1 calc R . . 
C18 C 0.1341(3) -0.1566(5) 0.89917(13) 0.0251(12) Uani 1 1 d . . . 
H18 H 0.1448 -0.2436 0.9127 0.030 Uiso 1 1 calc R . . 
C1 C 0.3479(3) 0.0895(5) 1.11356(13) 0.0271(12) Uani 1 1 d . . . 
H1D H 0.3722 0.1534 1.0934 0.033 Uiso 1 1 calc R . . 
H1E H 0.2893 0.1171 1.1171 0.033 Uiso 1 1 calc R . . 
C10 C 0.3074(3) 0.0958(6) 0.79285(14) 0.0451(15) Uani 1 1 d . . . 
H10A H 0.2505 0.0571 0.7933 0.054 Uiso 1 1 calc R . . 
H10B H 0.3072 0.1876 0.8074 0.054 Uiso 1 1 calc R . . 
 
 
_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 
P1 F6 1.643(3) . ? 
P1 F2 1.668(3) . ? 
P1 F5 1.670(3) . ? 
P1 F3 1.673(3) . ? 
P1 F1 1.691(3) . ? 
P1 F4 1.711(3) . ? 
O2 C8 1.233(5) . ? 
O1 C3 1.221(5) . ? 
N3 C7 1.362(5) . ? 
N3 C4 1.367(5) . ? 
N2 C3 1.345(5) . ? 
N2 C2 1.447(5) . ? 
C4 C5 1.401(6) . ? 
C4 C3 1.476(6) . ? 
C17 C18 1.384(6) . ? 
C17 C22 1.387(6) . ? 
C17 C6 1.498(6) . ? 
C7 C6 1.387(6) . ? 
C7 C8 1.482(6) . ? 
N4 C8 1.342(5) . ? 
N4 C9 1.462(5) . ? 
C11 C16 1.383(6) . ? 
C11 C12 1.403(6) . ? 
C11 C5 1.483(6) . ? 
C6 C5 1.421(6) . ? 
N1 C1 1.486(5) . ? 
C2 C1 1.523(7) . ? 
C22 C21 1.375(6) . ? 
C21 C20 1.386(7) . ? 
C14 C15 1.375(7) . ? 
C14 C13 1.379(7) . ? 
C9 C10 1.497(7) . ? 
C13 C12 1.379(6) . ? 
N5 C10 1.469(6) . ? 
C20 C19 1.374(7) . ? 
C16 C15 1.379(6) . ? 
C19 C18 1.378(6) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
F6 P1 F2 90.54(18) . . ? 
F6 P1 F5 90.10(17) . . ? 
F2 P1 F5 178.86(19) . . ? 
F6 P1 F3 179.27(18) . . ? 
F2 P1 F3 89.07(18) . . ? 
F5 P1 F3 90.28(19) . . ? 
F6 P1 F1 91.72(15) . . ? 
F2 P1 F1 90.99(15) . . ? 
F5 P1 F1 89.94(15) . . ? 
F3 P1 F1 88.90(14) . . ? 
F6 P1 F4 89.99(15) . . ? 
F2 P1 F4 88.70(15) . . ? 
F5 P1 F4 90.35(16) . . ? 
F3 P1 F4 89.38(14) . . ? 
F1 P1 F4 178.26(16) . . ? 
C7 N3 C4 109.7(3) . . ? 
C3 N2 C2 121.2(4) . . ? 
N3 C4 C5 108.2(4) . . ? 
N3 C4 C3 118.2(4) . . ? 
C5 C4 C3 133.6(4) . . ? 
C18 C17 C22 117.6(4) . . ? 
C18 C17 C6 121.6(4) . . ? 
C22 C17 C6 120.8(4) . . ? 
N3 C7 C6 108.2(4) . . ? 
N3 C7 C8 118.7(4) . . ? 
C6 C7 C8 133.0(4) . . ? 
C8 N4 C9 123.7(4) . . ? 
O2 C8 N4 123.0(4) . . ? 
O2 C8 C7 120.3(4) . . ? 
N4 C8 C7 116.8(4) . . ? 
C16 C11 C12 118.3(4) . . ? 
C16 C11 C5 121.7(4) . . ? 
C12 C11 C5 119.9(4) . . ? 
O1 C3 N2 121.9(4) . . ? 
O1 C3 C4 120.5(4) . . ? 
N2 C3 C4 117.6(4) . . ? 
C7 C6 C5 107.5(4) . . ? 
C7 C6 C17 126.5(4) . . ? 
C5 C6 C17 126.0(4) . . ? 
N2 C2 C1 109.2(4) . . ? 
C21 C22 C17 122.0(4) . . ? 
C22 C21 C20 119.3(5) . . ? 
C4 C5 C6 106.3(4) . . ? 
C4 C5 C11 127.0(4) . . ? 
C6 C5 C11 126.7(4) . . ? 
C15 C14 C13 119.8(4) . . ? 
N4 C9 C10 107.8(4) . . ? 
C12 C13 C14 119.5(5) . . ? 
C19 C20 C21 119.4(4) . . ? 
C15 C16 C11 120.2(5) . . ? 
C13 C12 C11 121.1(4) . . ? 
C20 C19 C18 120.7(5) . . ? 
C14 C15 C16 121.0(5) . . ? 
C19 C18 C17 120.9(5) . . ? 
N1 C1 C2 111.3(4) . . ? 
N5 C10 C9 112.5(4) . . ? 
 
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 
N5 H5B F3  0.91 1.99 2.811(5) 149.4 . 
N5 H5B F4  0.91 2.23 2.999(5) 142.1 . 
O2W H3W F5  0.9000(10) 2.30(11) 2.740(5) 110(8) . 
O1W H2W F1  0.9000(13) 2.11(11) 2.720(5) 125(11) . 
O2W H4W F4  0.9000(12) 1.851(12) 2.742(5) 170(6) 8_665 
N3 H3 O1  0.88 2.09 2.911(5) 155.7 5_657 
N1 H1C O2  0.91 1.96 2.806(5) 154.3 5_657 
N1 H1A F4  0.91 1.93 2.816(5) 163.5 2 
N1 H1A F6  0.91 2.50 3.066(5) 120.6 2 
N1 H1B O2W  0.91 1.92 2.758(5) 153.0 2_565 
N5 H5A O1W  0.91 1.94 2.789(6) 154.0 6_657 
N5 H5C F1  0.91 1.96 2.815(5) 156.2 8_655 
N5 H5C F3  0.91 2.28 2.999(5) 135.3 8_655 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              25.03 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.678 
_refine_diff_density_min   -0.512 
_refine_diff_density_rms    0.079 
