 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C13 H19 N2, F6 P'
_chemical_formula_sum
 'C13 H19 F6 N2 P'
_chemical_formula_weight          348.27
 
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    P21/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                    9.6325(3)
_cell_length_b                    16.6358(6)
_cell_length_c                    9.8585(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.591(2)
_cell_angle_gamma                 90.00
_cell_volume                      1535.53(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     45905
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.506
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              720
_exptl_absorpt_coefficient_mu     0.240
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9537
_exptl_absorpt_correction_T_max   0.9764
_exptl_absorpt_process_details    
'SORTAV (R. H. Blessing, Acta Cryst. A51'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             5255
_diffrn_reflns_av_R_equivalents   0.0258
_diffrn_reflns_av_sigmaI/netI     0.0390
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.60
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2703
_reflns_number_gt                 2336
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-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)+(0.0464P)²+0.7991P] 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        0.014(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2703
_refine_ls_number_parameters      202
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0448
_refine_ls_R_factor_gt            0.0377
_refine_ls_wR_factor_ref          0.1013
_refine_ls_wR_factor_gt           0.0975
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.032
_refine_ls_shift/su_max           0.028
_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
N1 N 1.10683(16) 0.05322(9) 0.29926(16) 0.0243(4) Uani 1 1 d . . .
N2 N 0.98164(16) 0.15296(9) 0.35277(15) 0.0241(4) Uani 1 1 d . . .
C1 C 1.3142(2) -0.05613(13) 0.0694(2) 0.0352(5) Uani 1 1 d . . .
H1A H 1.4019 -0.0242 0.0958 0.053 Uiso 1 1 calc R . .
H1B H 1.2922 -0.0666 -0.0312 0.053 Uiso 1 1 calc R . .
H1C H 1.3275 -0.1073 0.1202 0.053 Uiso 1 1 calc R . .
C2 C 1.1915(2) -0.01002(12) 0.1057(2) 0.0282(4) Uani 1 1 d . . .
H2A H 1.1759 0.0408 0.0520 0.034 Uiso 1 1 calc R . .
H2B H 1.1030 -0.0423 0.0795 0.034 Uiso 1 1 calc R . .
C3 C 1.2239(2) 0.00851(12) 0.2606(2) 0.0283(4) Uani 1 1 d . . .
H3A H 1.2399 -0.0425 0.3139 0.034 Uiso 1 1 calc R . .
H3B H 1.3127 0.0406 0.2865 0.034 Uiso 1 1 calc R . .
C4 C 1.1046(2) 0.13166(11) 0.32391(19) 0.0248(4) Uani 1 1 d . . .
H4 H 1.1805 0.1676 0.3213 0.030 Uiso 1 1 calc R . .
C5 C 0.9411(2) 0.23502(11) 0.38474(19) 0.0259(4) Uani 1 1 d . . .
H5A H 0.8399 0.2444 0.3370 0.031 Uiso 1 1 calc R . .
H5B H 0.9999 0.2741 0.3472 0.031 Uiso 1 1 calc R . .
C6 C 0.9600(2) 0.24987(12) 0.5393(2) 0.0305(5) Uani 1 1 d . . .
H6A H 1.0619 0.2438 0.5872 0.037 Uiso 1 1 calc R . .
H6B H 0.9043 0.2097 0.5785 0.037 Uiso 1 1 calc R . .
C7 C 0.9096(2) 0.33416(12) 0.5642(2) 0.0312(5) Uani 1 1 d . . .
H7A H 0.9604 0.3736 0.5201 0.047 Uiso 1 1 calc R . .
H7B H 0.9291 0.3446 0.6648 0.047 Uiso 1 1 calc R . .
H7C H 0.8067 0.3385 0.5238 0.047 Uiso 1 1 calc R . .
C8 C 0.97643(19) 0.02083(11) 0.31051(18) 0.0243(4) Uani 1 1 d . . .
C9 C 0.9230(2) -0.05717(12) 0.29283(19) 0.0284(4) Uani 1 1 d . . .
H9 H 0.9760 -0.1002 0.2665 0.034 Uiso 1 1 calc R . .
C10 C 0.7881(2) -0.06837(12) 0.3159(2) 0.0330(5) Uani 1 1 d . . .
H10 H 0.7477 -0.1207 0.3063 0.040 Uiso 1 1 calc R . .
C11 C 0.7094(2) -0.00466(13) 0.3529(2) 0.0325(5) Uani 1 1 d . . .
H11 H 0.6174 -0.0153 0.3683 0.039 Uiso 1 1 calc R . .
C12 C 0.7606(2) 0.07294(12) 0.36801(19) 0.0284(4) Uani 1 1 d . . .
H12 H 0.7063 0.1161 0.3920 0.034 Uiso 1 1 calc R . .
C13 C 0.8973(2) 0.08429(11) 0.34579(18) 0.0240(4) Uani 1 1 d . . .
P1 P 0.47478(5) 0.24099(3) 0.48198(5) 0.02549(18) Uani 1 1 d . . .
F1 F 0.35664(12) 0.26935(7) 0.34792(11) 0.0350(3) Uani 1 1 d . . .
F2 F 0.35372(13) 0.23459(8) 0.56780(12) 0.0405(3) Uani 1 1 d . . .
F3 F 0.44604(13) 0.14883(7) 0.43353(12) 0.0374(3) Uani 1 1 d . . .
F4 F 0.59264(12) 0.21224(8) 0.61534(12) 0.0401(3) Uani 1 1 d . . .
F5 F 0.59403(12) 0.24736(7) 0.39367(12) 0.0362(3) Uani 1 1 d . . .
F6 F 0.50408(13) 0.33228(7) 0.53038(12) 0.0377(3) 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
N1 C4 1.328(2) . ?
N1 C8 1.395(2) . ?
N1 C3 1.473(2) . ?
N2 C4 1.329(2) . ?
N2 C13 1.394(2) . ?
N2 C5 1.474(2) . ?
C1 C2 1.520(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 0.9500 . ?
C5 C6 1.511(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.392(3) . ?
C8 C13 1.393(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(3) . ?
C12 H12 0.9500 . ?
P1 F4 1.5952(12) . ?
P1 F2 1.5971(12) . ?
P1 F6 1.5971(12) . ?
P1 F1 1.5992(12) . ?
P1 F5 1.5996(12) . ?
P1 F3 1.6103(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
C4 N1 C8 108.12(15) . . ?
C4 N1 C3 126.13(16) . . ?
C8 N1 C3 125.70(16) . . ?
C4 N2 C13 108.00(15) . . ?
C4 N2 C5 125.93(15) . . ?
C13 N2 C5 126.06(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 110.65(16) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C2 111.98(15) . . ?
N1 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 N2 110.78(16) . . ?
N1 C4 H4 124.6 . . ?
N2 C4 H4 124.6 . . ?
N2 C5 C6 113.05(15) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 110.23(16) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 131.59(18) . . ?
C9 C8 C13 121.98(17) . . ?
N1 C8 C13 106.43(16) . . ?
C10 C9 C8 116.05(18) . . ?
C10 C9 H9 122.0 . . ?
C8 C9 H9 122.0 . . ?
C9 C10 C11 121.84(19) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 122.39(19) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 115.87(18) . . ?
C11 C12 H12 122.1 . . ?
C13 C12 H12 122.1 . . ?
N2 C13 C8 106.65(16) . . ?
N2 C13 C12 131.50(17) . . ?
C8 C13 C12 121.84(17) . . ?
F4 P1 F2 90.59(7) . . ?
F4 P1 F6 89.84(7) . . ?
F2 P1 F6 90.28(7) . . ?
F4 P1 F1 179.70(7) . . ?
F2 P1 F1 89.49(6) . . ?
F6 P1 F1 90.45(7) . . ?
F4 P1 F5 90.31(7) . . ?
F2 P1 F5 179.05(7) . . ?
F6 P1 F5 90.03(7) . . ?
F1 P1 F5 89.61(6) . . ?
F4 P1 F3 89.91(7) . . ?
F2 P1 F3 89.87(7) . . ?
F6 P1 F3 179.72(8) . . ?
F1 P1 F3 89.80(7) . . ?
F5 P1 F3 89.83(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.229
_refine_diff_density_min   -0.302
_refine_diff_density_rms    0.050
