data_04src0088
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H15 F6 N2 P'
_chemical_formula_weight          320.22
 
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'
 '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
_symmetry_space_group_name_hall   '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    9.20170(10)
_cell_length_b                    16.0731(3)
_cell_length_c                    18.2782(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2703.34(8)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     35728
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.574
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1312
_exptl_absorpt_coefficient_mu     0.265
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8902
_exptl_absorpt_correction_T_max   0.9490
_exptl_absorpt_process_details    'SORTAV (R.H.BLessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        '\\f and \\w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_decay_%         'negligible'
_diffrn_reflns_number             24154
_diffrn_reflns_av_R_equivalents   0.0861
_diffrn_reflns_av_sigmaI/netI     0.0341
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.14
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3078
_reflns_number_gt                 2653
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.0650P)²+1.6559P] where P=(Fo²+2Fc²)/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      SHELXL
_refine_ls_extinction_coef        0.0111(11)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3078
_refine_ls_number_parameters      184
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0505
_refine_ls_R_factor_gt            0.0431
_refine_ls_wR_factor_ref          0.1265
_refine_ls_wR_factor_gt           0.1204
_refine_ls_goodness_of_fit_ref    1.038
_refine_ls_restrained_S_all       1.038
_refine_ls_shift/su_max           0.021
_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
C1 C 0.69613(17) 0.41200(9) 0.57014(9) 0.0215(3) Uani 1 1 d . . .
C2 C 0.78104(19) 0.42809(11) 0.50895(9) 0.0257(4) Uani 1 1 d . . .
H2 H 0.8423 0.3870 0.4880 0.031 Uiso 1 1 calc R . .
C3 C 0.7710(2) 0.50746(11) 0.48042(10) 0.0294(4) Uani 1 1 d . . .
H3 H 0.8277 0.5215 0.4387 0.035 Uiso 1 1 calc R . .
C4 C 0.6799(2) 0.56789(10) 0.51111(10) 0.0282(4) Uani 1 1 d . . .
H4 H 0.6755 0.6214 0.4892 0.034 Uiso 1 1 calc R . .
C5 C 0.59613(19) 0.55219(10) 0.57227(9) 0.0246(4) Uani 1 1 d . . .
H5 H 0.5347 0.5933 0.5932 0.030 Uiso 1 1 calc R . .
C6 C 0.60711(17) 0.47251(10) 0.60135(9) 0.0212(3) Uani 1 1 d . . .
C7 C 0.58532(18) 0.35672(10) 0.66529(9) 0.0225(3) Uani 1 1 d . . .
H7 H 0.5551 0.3178 0.7014 0.027 Uiso 1 1 calc R . .
C8 C 0.7455(2) 0.25943(10) 0.59728(10) 0.0282(4) Uani 1 1 d . . .
H8A H 0.7439 0.2257 0.6419 0.042 Uiso 1 1 calc R . .
H8B H 0.8462 0.2674 0.5814 0.042 Uiso 1 1 calc R . .
H8C H 0.6909 0.2309 0.5587 0.042 Uiso 1 1 calc R . .
C9 C 0.44630(18) 0.47679(10) 0.71490(9) 0.0245(4) Uani 1 1 d . . .
H9A H 0.3931 0.4344 0.7437 0.029 Uiso 1 1 calc R . .
H9B H 0.3738 0.5114 0.6889 0.029 Uiso 1 1 calc R . .
C10 C 0.53422(19) 0.53129(11) 0.76623(10) 0.0277(4) Uani 1 1 d . . .
H10A H 0.6083 0.4969 0.7913 0.033 Uiso 1 1 calc R . .
H10B H 0.5854 0.5746 0.7376 0.033 Uiso 1 1 calc R . .
C11 C 0.4377(2) 0.57255(12) 0.82273(11) 0.0333(4) Uani 1 1 d . . .
H11A H 0.3620 0.6049 0.7979 0.050 Uiso 1 1 calc R . .
H11B H 0.4963 0.6096 0.8534 0.050 Uiso 1 1 calc R . .
H11C H 0.3922 0.5298 0.8534 0.050 Uiso 1 1 calc R . .
N1 N 0.67886(15) 0.34046(8) 0.61195(7) 0.0220(3) Uani 1 1 d . . .
N2 N 0.53975(15) 0.43505(8) 0.66120(8) 0.0217(3) Uani 1 1 d . . .
F1 F 0.21512(14) 0.15112(7) 0.64947(7) 0.0422(3) Uani 1 1 d . . .
F2 F 0.05377(12) 0.24513(7) 0.69217(7) 0.0385(3) Uani 1 1 d . . .
F3 F 0.29125(13) 0.25743(8) 0.72035(7) 0.0409(3) Uani 1 1 d . . .
F4 F 0.18901(17) 0.34874(7) 0.64330(7) 0.0521(4) Uani 1 1 d . . .
F5 F 0.34889(13) 0.25415(6) 0.59983(6) 0.0339(3) Uani 1 1 d . . .
F6 F 0.11117(14) 0.24246(8) 0.57187(6) 0.0435(3) Uani 1 1 d . . .
P1 P 0.20117(5) 0.25000(2) 0.64610(2) 0.02283(16) Uani 1 1 d . . .
 
 
_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 1.388(2) . ?
C1 N1 1.390(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 N2 1.394(2) . ?
C7 N1 1.327(2) . ?
C7 N2 1.329(2) . ?
C7 H7 0.9500 . ?
C8 N1 1.464(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.467(2) . ?
C9 C10 1.517(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.515(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
F1 P1 1.5956(12) . ?
F2 P1 1.5983(12) . ?
F3 P1 1.5946(12) . ?
F4 P1 1.5918(12) . ?
F5 P1 1.6023(12) . ?
F6 P1 1.5942(12) . ?
 
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 131.40(15) . . ?
C2 C1 C6 122.04(15) . . ?
N1 C1 C6 106.56(14) . . ?
C3 C2 C1 116.02(16) . . ?
C3 C2 H2 122.0 . . ?
C1 C2 H2 122.0 . . ?
C2 C3 C4 121.94(17) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 122.12(16) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 115.93(15) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
C5 C6 C1 121.94(15) . . ?
C5 C6 N2 131.73(15) . . ?
C1 C6 N2 106.33(14) . . ?
N1 C7 N2 110.49(14) . . ?
N1 C7 H7 124.8 . . ?
N2 C7 H7 124.8 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 111.42(14) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 111.20(15) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 N1 C1 108.38(13) . . ?
C7 N1 C8 125.56(14) . . ?
C1 N1 C8 125.96(14) . . ?
C7 N2 C6 108.24(13) . . ?
C7 N2 C9 125.48(14) . . ?
C6 N2 C9 126.01(14) . . ?
F4 P1 F6 90.68(7) . . ?
F4 P1 F3 89.39(7) . . ?
F6 P1 F3 179.93(8) . . ?
F4 P1 F1 179.31(9) . . ?
F6 P1 F1 89.93(7) . . ?
F3 P1 F1 90.00(7) . . ?
F4 P1 F2 90.36(7) . . ?
F6 P1 F2 90.22(6) . . ?
F3 P1 F2 89.80(6) . . ?
F1 P1 F2 89.95(6) . . ?
F4 P1 F5 90.07(7) . . ?
F6 P1 F5 89.69(7) . . ?
F3 P1 F5 90.29(6) . . ?
F1 P1 F5 89.63(6) . . ?
F2 P1 F5 179.57(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.426
_refine_diff_density_min   -0.431
_refine_diff_density_rms    0.079
