 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H17 F6 N2 P'
_chemical_formula_weight          334.25
 
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            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.8197(5)
_cell_length_b                    11.9252(7)
_cell_length_c                    11.2662(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.577(4)
_cell_angle_gamma                 90.00
_cell_volume                      1452.17(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     32732
_cell_measurement_theta_min       1.02
_cell_measurement_theta_max       20.6
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.60
_exptl_crystal_size_min           0.40
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.529
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              688
_exptl_absorpt_coefficient_mu     0.250
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8646
_exptl_absorpt_correction_T_max   0.9067
_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_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15921
_diffrn_reflns_av_R_equivalents   0.0692
_diffrn_reflns_av_sigmaI/netI     0.0242
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.49
_diffrn_reflns_theta_max          20.61
_reflns_number_total              1469
_reflns_number_gt                 1366
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_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   SHELXS-97
 
_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 > 2σ(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)+(0.0637P)²+0.3214P] 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        0.069(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1469
_refine_ls_number_parameters      194
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0408
_refine_ls_R_factor_gt            0.0386
_refine_ls_wR_factor_ref          0.1051
_refine_ls_wR_factor_gt           0.1029
_refine_ls_goodness_of_fit_ref    1.280
_refine_ls_restrained_S_all       1.280
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.5209(2) -0.11539(19) 0.3808(2) 0.0250(7) Uani 1 1 d . . .
C2 C 0.5770(2) -0.1872(2) 0.4642(2) 0.0316(7) Uani 1 1 d . . .
H2 H 0.6595 -0.2128 0.4579 0.038 Uiso 1 1 calc R . .
C3 C 0.5055(3) -0.2188(2) 0.5564(2) 0.0368(7) Uani 1 1 d . . .
H3 H 0.5405 -0.2670 0.6161 0.044 Uiso 1 1 calc R . .
C4 C 0.3842(3) -0.1829(2) 0.5654(2) 0.0374(8) Uani 1 1 d . . .
H4 H 0.3387 -0.2076 0.6307 0.045 Uiso 1 1 calc R . .
C5 C 0.3280(2) -0.1129(2) 0.4828(2) 0.0324(7) Uani 1 1 d . . .
H5 H 0.2448 -0.0888 0.4888 0.039 Uiso 1 1 calc R . .
C6 C 0.3994(2) -0.0793(2) 0.3902(2) 0.0253(7) Uani 1 1 d . . .
C7 C 0.4751(2) 0.0002(2) 0.2343(2) 0.0299(7) Uani 1 1 d . . .
H7 H 0.4821 0.0446 0.1648 0.036 Uiso 1 1 calc R . .
C8 C 0.6891(2) -0.0746(3) 0.2376(2) 0.0427(8) Uani 1 1 d . . .
H8A H 0.7017 -0.1515 0.2101 0.064 Uiso 1 1 calc R . .
H8B H 0.7501 -0.0572 0.3019 0.064 Uiso 1 1 calc R . .
H8C H 0.6990 -0.0223 0.1716 0.064 Uiso 1 1 calc R . .
C9 C 0.2578(2) 0.0548(2) 0.2737(2) 0.0320(7) Uani 1 1 d . . .
H9A H 0.2749 0.1268 0.2339 0.038 Uiso 1 1 calc R . .
H9B H 0.2212 0.0721 0.3506 0.038 Uiso 1 1 calc R . .
C10 C 0.1652(2) -0.0115(2) 0.1970(2) 0.0304(7) Uani 1 1 d . . .
H10 H 0.1682 -0.0914 0.2240 0.036 Uiso 1 1 calc R . .
C11 C 0.1982(2) -0.0080(2) 0.0670(2) 0.0362(7) Uani 1 1 d . . .
H11A H 0.1926 0.0694 0.0380 0.054 Uiso 1 1 calc R . .
H11B H 0.1406 -0.0553 0.0199 0.054 Uiso 1 1 calc R . .
H11C H 0.2828 -0.0356 0.0596 0.054 Uiso 1 1 calc R . .
C12 C 0.0356(2) 0.0327(3) 0.2134(2) 0.0412(8) Uani 1 1 d . . .
H12A H 0.0149 0.0242 0.2967 0.062 Uiso 1 1 calc R . .
H12B H -0.0236 -0.0098 0.1626 0.062 Uiso 1 1 calc R . .
H12C H 0.0319 0.1121 0.1914 0.062 Uiso 1 1 calc R . .
N1 N 0.56493(18) -0.06369(17) 0.28121(17) 0.0282(6) Uani 1 1 d . . .
N2 N 0.37489(17) -0.00562(16) 0.29630(17) 0.0245(6) Uani 1 1 d . . .
F1 F 0.13814(13) 0.29429(13) 0.60544(12) 0.0414(5) Uani 1 1 d . . .
F2 F 0.08593(15) 0.12230(12) 0.53430(14) 0.0478(5) Uani 1 1 d . . .
F3 F 0.12280(14) 0.26257(12) 0.40713(13) 0.0399(5) Uani 1 1 d . . .
F4 F -0.07174(13) 0.19944(14) 0.42382(13) 0.0451(5) Uani 1 1 d . . .
F5 F -0.01772(14) 0.37099(12) 0.49385(12) 0.0418(5) Uani 1 1 d . . .
F6 F -0.05603(15) 0.23118(14) 0.62175(14) 0.0463(5) Uani 1 1 d . . .
P1 P 0.03324(6) 0.24554(5) 0.51402(6) 0.0310(4) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.384(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.390(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.392(3) . ?
C7 N2 1.318(3) . ?
C7 N1 1.326(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.457(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.470(3) . ?
C9 C10 1.517(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C12 1.517(4) . ?
C10 C11 1.524(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
F1 P1 1.6068(15) . ?
F2 P1 1.5891(16) . ?
F3 P1 1.5923(15) . ?
F4 P1 1.5879(16) . ?
F5 P1 1.6070(15) . ?
F6 P1 1.5940(16) . ?
 
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
N1 C1 C6 106.6(2) . . ?
N1 C1 C2 131.8(2) . . ?
C6 C1 C2 121.6(2) . . ?
C3 C2 C1 115.9(2) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 116.2(2) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C5 C6 C1 121.9(2) . . ?
C5 C6 N2 131.4(2) . . ?
C1 C6 N2 106.6(2) . . ?
N2 C7 N1 111.3(2) . . ?
N2 C7 H7 124.3 . . ?
N1 C7 H7 124.3 . . ?
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 112.66(19) . . ?
N2 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C12 C10 C9 109.9(2) . . ?
C12 C10 C11 111.4(2) . . ?
C9 C10 C11 110.8(2) . . ?
C12 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
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 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 N1 C1 107.8(2) . . ?
C7 N1 C8 126.0(2) . . ?
C1 N1 C8 126.2(2) . . ?
C7 N2 C6 107.65(19) . . ?
C7 N2 C9 127.3(2) . . ?
C6 N2 C9 125.1(2) . . ?
F4 P1 F2 90.78(9) . . ?
F4 P1 F3 90.13(8) . . ?
F2 P1 F3 90.01(8) . . ?
F4 P1 F6 90.55(8) . . ?
F2 P1 F6 90.97(9) . . ?
F3 P1 F6 178.80(9) . . ?
F4 P1 F1 178.96(8) . . ?
F2 P1 F1 90.23(9) . . ?
F3 P1 F1 90.13(8) . . ?
F6 P1 F1 89.17(8) . . ?
F4 P1 F5 90.04(9) . . ?
F2 P1 F5 179.04(9) . . ?
F3 P1 F5 89.48(8) . . ?
F6 P1 F5 89.53(8) . . ?
F1 P1 F5 88.95(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              20.61
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.294
_refine_diff_density_min   -0.327
_refine_diff_density_rms    0.117
