 
data_2008src1000p2n
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C27 H36 B Cl F2 N2'
_chemical_formula_weight          472.84
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y, z-1/2'
 
_cell_length_a                    12.4636(8)
_cell_length_b                    7.3364(8)
_cell_length_c                    15.1611(16)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.529(6)
_cell_angle_gamma                 90.00
_cell_volume                      1385.8(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     10070
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.08
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.133
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              504
_exptl_absorpt_coefficient_mu     0.167
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9867
_exptl_absorpt_correction_T_max   0.9983
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_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    '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12239
_diffrn_reflns_av_R_equivalents   0.1728
_diffrn_reflns_av_sigmaI/netI     0.1928
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.27
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3138
_reflns_number_gt                 1280
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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.

 The BF2Cl group is highly disordered; when the atoms were further split the
 refinement became unstable and therefore the group was only split into two 
 parts in spite of the large ellipsoids. The large ellpsoids of the methyl 
 groups also suggest they are slightly disordered due to the flexibiltiy of 
 the bond.

 The high Rint and R-values are due to the weakly diffracting nature and 
 small size of the crystals.
;
 
_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)+(0.0000P)²+5.5466P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3138
_refine_ls_number_parameters      167
_refine_ls_number_restraints      108
_refine_ls_R_factor_all           0.3297
_refine_ls_R_factor_gt            0.1746
_refine_ls_wR_factor_ref          0.3107
_refine_ls_wR_factor_gt           0.2436
_refine_ls_goodness_of_fit_ref    1.124
_refine_ls_restrained_S_all       1.108
_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 0.3724(5) 0.2171(8) 0.3823(3) 0.0371(15) Uani 1 1 d U . .
C2 C 0.3265(5) 0.2324(9) 0.4637(4) 0.0457(17) Uani 1 1 d U . .
C3 C 0.3976(5) 0.2630(10) 0.5360(4) 0.0529(19) Uani 1 1 d U . .
H3 H 0.3702 0.2759 0.5935 0.064 Uiso 1 1 calc R . .
C4 C 0.5063(5) 0.2743(9) 0.5240(4) 0.0509(18) Uani 1 1 d U . .
H4 H 0.5534 0.2924 0.5735 0.061 Uiso 1 1 calc R . .
C5 C 0.5473(5) 0.2599(9) 0.4414(4) 0.0506(18) Uani 1 1 d U . .
H5 H 0.6226 0.2696 0.4344 0.061 Uiso 1 1 calc R . .
C6 C 0.4811(5) 0.2315(9) 0.3681(4) 0.0410(16) Uani 1 1 d U . .
C7 C 0.5263(6) 0.2168(12) 0.2755(5) 0.067(2) Uani 1 1 d U . .
H7 H 0.4641 0.2180 0.2324 0.081 Uiso 1 1 calc R . .
C8 C 0.5851(7) 0.0351(14) 0.2643(6) 0.102(3) Uani 1 1 d U . .
H8A H 0.6447 0.0273 0.3077 0.152 Uiso 1 1 calc R . .
H8B H 0.6131 0.0276 0.2047 0.152 Uiso 1 1 calc R . .
H8C H 0.5351 -0.0658 0.2736 0.152 Uiso 1 1 calc R . .
C9 C 0.5973(7) 0.3819(14) 0.2549(6) 0.113(4) Uani 1 1 d U . .
H9A H 0.5567 0.4944 0.2642 0.169 Uiso 1 1 calc R . .
H9B H 0.6192 0.3758 0.1934 0.169 Uiso 1 1 calc R . .
H9C H 0.6611 0.3808 0.2941 0.169 Uiso 1 1 calc R . .
C10 C 0.2061(5) 0.2157(12) 0.4785(5) 0.066(2) Uani 1 1 d U . .
H10 H 0.1684 0.2345 0.4202 0.080 Uiso 1 1 calc R . .
C11 C 0.1632(7) 0.3535(17) 0.5411(7) 0.139(5) Uani 1 1 d U . .
H11A H 0.2024 0.3447 0.5978 0.208 Uiso 1 1 calc R . .
H11B H 0.0868 0.3302 0.5498 0.208 Uiso 1 1 calc R . .
H11C H 0.1722 0.4760 0.5166 0.208 Uiso 1 1 calc R . .
C12 C 0.1797(6) 0.0182(15) 0.5098(6) 0.097(3) Uani 1 1 d U . .
H12A H 0.2186 -0.0070 0.5655 0.146 Uiso 1 1 calc R . .
H12B H 0.2016 -0.0696 0.4650 0.146 Uiso 1 1 calc R . .
H12C H 0.1023 0.0073 0.5186 0.146 Uiso 1 1 calc R . .
C14 C 0.2500 0.2806(12) 0.2500 0.037(2) Uani 1 2 d SU . .
C15 C 0.2830(5) -0.0118(9) 0.2858(4) 0.0493(18) Uani 1 1 d U . .
H15 H 0.3115 -0.1157 0.3156 0.059 Uiso 1 1 calc R A .
N13 N 0.3012(4) 0.1668(7) 0.3076(3) 0.0424(14) Uani 1 1 d U A .
B1 B 0.2337(13) 0.5002(15) 0.2586(12) 0.028(3) Uiso 0.50 1 d PU A -1
F1 F 0.2169(13) 0.5663(19) 0.1706(10) 0.101(6) Uani 0.50 1 d PU A -1
F2 F 0.3379(11) 0.5708(17) 0.2831(9) 0.072(4) Uani 0.50 1 d PU A -1
Cl1 Cl 0.1395(7) 0.5754(8) 0.3297(6) 0.164(3) Uani 0.50 1 d P A -1
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.054(4) 0.036(4) 0.020(3) -0.003(3) -0.008(3) 0.011(3)
C2 0.048(4) 0.060(5) 0.029(3) -0.001(3) -0.004(3) 0.015(3)
C3 0.057(4) 0.072(5) 0.030(3) 0.005(4) -0.006(3) 0.003(4)
C4 0.058(4) 0.057(5) 0.037(4) 0.004(3) -0.017(3) 0.002(4)
C5 0.043(4) 0.059(5) 0.050(4) 0.008(4) -0.006(3) -0.001(3)
C6 0.050(4) 0.040(4) 0.033(3) 0.010(3) 0.000(3) 0.003(3)
C7 0.068(5) 0.090(6) 0.045(4) 0.012(4) 0.010(4) -0.014(5)
C8 0.119(8) 0.119(9) 0.069(6) -0.006(6) 0.039(5) 0.036(7)
C9 0.111(8) 0.143(10) 0.086(7) 0.042(7) 0.029(6) -0.052(7)
C10 0.044(4) 0.111(7) 0.044(4) -0.011(5) -0.002(3) 0.011(4)
C11 0.079(7) 0.224(14) 0.113(8) -0.095(9) -0.004(6) 0.056(8)
C12 0.046(5) 0.160(10) 0.086(7) 0.022(7) 0.004(4) -0.016(6)
C14 0.054(5) 0.033(5) 0.024(4) 0.000 -0.009(4) 0.000
C15 0.088(5) 0.023(3) 0.037(4) 0.006(3) -0.009(3) 0.001(3)
N13 0.060(3) 0.035(3) 0.031(3) -0.001(2) -0.010(2) 0.008(3)
F1 0.172(17) 0.041(6) 0.087(11) -0.007(8) -0.083(9) -0.009(10)
F2 0.092(9) 0.024(5) 0.097(11) -0.005(7) -0.042(6) -0.005(6)
Cl1 0.199(8) 0.052(3) 0.244(9) -0.003(5) 0.097(6) 0.009(4)
 
_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 C2 1.379(7) . ?
C1 C6 1.381(8) . ?
C1 N13 1.467(7) . ?
C2 C3 1.409(8) . ?
C2 C10 1.528(9) . ?
C3 C4 1.374(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.532(9) . ?
C7 C8 1.532(11) . ?
C7 C9 1.536(11) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.496(11) . ?
C10 C12 1.563(12) . ?
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 . ?
C14 N13 1.355(7) 2 ?
C14 N13 1.355(7) . ?
C14 B1 1.630(14) 2 ?
C14 B1 1.630(14) . ?
C15 C15 1.346(11) 2 ?
C15 N13 1.369(7) . ?
C15 H15 0.9500 . ?
B1 F1 1.43(2) . ?
B1 F2 1.44(2) . ?
B1 Cl1 1.708(15) . ?
 
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 C6 124.4(5) . . ?
C2 C1 N13 117.0(5) . . ?
C6 C1 N13 118.4(5) . . ?
C1 C2 C3 116.2(6) . . ?
C1 C2 C10 123.9(5) . . ?
C3 C2 C10 119.9(6) . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.2(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.0(5) . . ?
C1 C6 C7 121.5(5) . . ?
C5 C6 C7 121.5(6) . . ?
C6 C7 C8 110.5(6) . . ?
C6 C7 C9 111.0(7) . . ?
C8 C7 C9 112.6(7) . . ?
C6 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C9 C7 H7 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 114.1(7) . . ?
C11 C10 C12 110.6(8) . . ?
C2 C10 C12 109.6(6) . . ?
C11 C10 H10 107.4 . . ?
C2 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
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 . . ?
N13 C14 N13 104.0(7) 2 . ?
N13 C14 B1 127.9(8) 2 2 ?
N13 C14 B1 127.1(8) . 2 ?
N13 C14 B1 127.1(8) 2 . ?
N13 C14 B1 127.9(8) . . ?
B1 C14 B1 17.2(10) 2 . ?
C15 C15 N13 106.8(3) 2 . ?
C15 C15 H15 126.6 2 . ?
N13 C15 H15 126.6 . . ?
C14 N13 C15 111.2(5) . . ?
C14 N13 C1 127.4(5) . . ?
C15 N13 C1 121.3(5) . . ?
F1 B1 F2 103.2(9) . . ?
F1 B1 C14 106.0(11) . . ?
F2 B1 C14 105.3(11) . . ?
F1 B1 Cl1 113.1(13) . . ?
F2 B1 Cl1 110.6(12) . . ?
C14 B1 Cl1 117.3(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.351
_refine_diff_density_min   -0.335
_refine_diff_density_rms    0.060
