 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H19 B F4 N2'
_chemical_formula_weight          290.11
 
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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.6774(3)
_cell_length_b                    9.0176(3)
_cell_length_c                    10.0740(3)
_cell_angle_alpha                 107.625(2)
_cell_angle_beta                  96.197(2)
_cell_angle_gamma                 102.871(2)
_cell_volume                      719.23(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11522
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.340
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              304
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9448
_exptl_absorpt_correction_T_max   0.9886
_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             14070
_diffrn_reflns_av_R_equivalents   0.1318
_diffrn_reflns_av_sigmaI/netI     0.0641
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3278
_reflns_number_gt                 2899
_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)+(0.0448P)²+0.3684P] 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        0.084(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3278
_refine_ls_number_parameters      185
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0575
_refine_ls_R_factor_gt            0.0517
_refine_ls_wR_factor_ref          0.1338
_refine_ls_wR_factor_gt           0.1286
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.031
_refine_ls_shift/su_max           0.004
_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
B1 B 0.2740(2) 0.5130(2) 0.8069(2) 0.0306(4) Uani 1 1 d . . .
F1 F 0.17909(16) 0.43893(18) 0.67454(14) 0.0640(4) Uani 1 1 d . . .
F2 F 0.35800(13) 0.66887(12) 0.82170(13) 0.0444(3) Uani 1 1 d . . .
F3 F 0.17931(13) 0.51770(12) 0.91009(12) 0.0425(3) Uani 1 1 d . . .
F4 F 0.38526(13) 0.42657(13) 0.82603(12) 0.0425(3) Uani 1 1 d . . .
C1 C 0.20769(16) 0.05058(17) 0.07907(15) 0.0241(3) Uani 1 1 d . . .
C2 C 0.16563(18) -0.11182(18) 0.06627(18) 0.0303(3) Uani 1 1 d . . .
H2 H 0.1950 -0.1910 -0.0052 0.036 Uiso 1 1 calc R . .
C3 C 0.07861(19) -0.1513(2) 0.1636(2) 0.0354(4) Uani 1 1 d . . .
H3 H 0.0463 -0.2611 0.1582 0.042 Uiso 1 1 calc R . .
C4 C 0.03669(19) -0.0347(2) 0.2697(2) 0.0359(4) Uani 1 1 d . . .
H4 H -0.0219 -0.0674 0.3350 0.043 Uiso 1 1 calc R . .
C5 C 0.07800(18) 0.1269(2) 0.28224(17) 0.0307(3) Uani 1 1 d . . .
H5 H 0.0492 0.2061 0.3541 0.037 Uiso 1 1 calc R . .
C6 C 0.16398(16) 0.16643(17) 0.18363(15) 0.0238(3) Uani 1 1 d . . .
C7 C 0.29605(17) 0.28732(17) 0.05407(16) 0.0256(3) Uani 1 1 d . . .
H7 H 0.3464 0.3688 0.0191 0.031 Uiso 1 1 calc R . .
C8 C 0.3630(2) 0.0630(2) -0.12020(17) 0.0334(4) Uani 1 1 d . . .
H8A H 0.3572 0.1225 -0.1867 0.050 Uiso 1 1 calc R . .
H8B H 0.3041 -0.0507 -0.1682 0.050 Uiso 1 1 calc R . .
H8C H 0.4759 0.0710 -0.0868 0.050 Uiso 1 1 calc R . .
C9 C 0.20796(19) 0.47289(17) 0.24746(16) 0.0281(3) Uani 1 1 d . . .
H9A H 0.1016 0.4613 0.2762 0.034 Uiso 1 1 calc R . .
H9B H 0.2156 0.5436 0.1887 0.034 Uiso 1 1 calc R . .
C10 C 0.34031(17) 0.55123(17) 0.37936(15) 0.0242(3) Uani 1 1 d . . .
H10A H 0.4432 0.5323 0.3543 0.029 Uiso 1 1 calc R . .
H10B H 0.3136 0.5002 0.4512 0.029 Uiso 1 1 calc R . .
C11 C 0.36064(18) 0.73292(17) 0.44252(15) 0.0260(3) Uani 1 1 d . . .
H11 H 0.3726 0.7801 0.3650 0.031 Uiso 1 1 calc R . .
C12 C 0.5141(2) 0.81115(19) 0.55600(18) 0.0350(4) Uani 1 1 d . . .
H12A H 0.5269 0.9276 0.5961 0.053 Uiso 1 1 calc R . .
H12B H 0.6072 0.7922 0.5132 0.053 Uiso 1 1 calc R . .
H12C H 0.5064 0.7636 0.6314 0.053 Uiso 1 1 calc R . .
C13 C 0.2155(2) 0.7698(2) 0.50406(17) 0.0337(4) Uani 1 1 d . . .
H13A H 0.2037 0.7273 0.5822 0.051 Uiso 1 1 calc R . .
H13B H 0.1184 0.7190 0.4301 0.051 Uiso 1 1 calc R . .
H13C H 0.2309 0.8870 0.5395 0.051 Uiso 1 1 calc R . .
N1 N 0.29146(15) 0.13197(15) 0.00025(13) 0.0250(3) Uani 1 1 d . . .
N2 N 0.22100(15) 0.31290(14) 0.16286(13) 0.0242(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
B1 F1 1.371(2) . ?
B1 F2 1.386(2) . ?
B1 F3 1.390(2) . ?
B1 F4 1.401(2) . ?
C1 C2 1.390(2) . ?
C1 N1 1.392(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 N2 1.3898(19) . ?
C7 N2 1.321(2) . ?
C7 N1 1.3299(19) . ?
C7 H7 0.9500 . ?
C8 N1 1.457(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.4730(18) . ?
C9 C10 1.525(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5284(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.520(2) . ?
C11 C12 1.530(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
 
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
F1 B1 F2 110.19(15) . . ?
F1 B1 F3 109.96(14) . . ?
F2 B1 F3 109.63(14) . . ?
F1 B1 F4 109.78(16) . . ?
F2 B1 F4 108.50(13) . . ?
F3 B1 F4 108.75(14) . . ?
C2 C1 N1 131.64(14) . . ?
C2 C1 C6 121.86(14) . . ?
N1 C1 C6 106.49(12) . . ?
C3 C2 C1 116.09(15) . . ?
C3 C2 H2 122.0 . . ?
C1 C2 H2 122.0 . . ?
C2 C3 C4 122.03(15) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.94(16) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 116.06(16) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
C5 C6 N2 131.53(14) . . ?
C5 C6 C1 122.01(14) . . ?
N2 C6 C1 106.45(13) . . ?
N2 C7 N1 110.77(13) . . ?
N2 C7 H7 124.6 . . ?
N1 C7 H7 124.6 . . ?
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 111.37(12) . . ?
N2 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.64(12) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C13 C11 C10 111.91(13) . . ?
C13 C11 C12 110.51(13) . . ?
C10 C11 C12 109.69(12) . . ?
C13 C11 H11 108.2 . . ?
C10 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C1 107.95(13) . . ?
C7 N1 C8 124.84(13) . . ?
C1 N1 C8 127.22(13) . . ?
C7 N2 C6 108.33(12) . . ?
C7 N2 C9 124.08(13) . . ?
C6 N2 C9 127.56(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.315
_refine_diff_density_min   -0.271
_refine_diff_density_rms    0.056
