 
data_2009src0344
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H9 Cl3 F3 N O Si'
_chemical_formula_weight          338.61
 
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'
 'O'  'O'   0.0106   0.0060
 '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'
 'Si'  'Si'   0.0817   0.0704
 '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    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    9.0871(3)
_cell_length_b                    7.3467(2)
_cell_length_c                    21.0204(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.7870(10)
_cell_angle_gamma                 90.00
_cell_volume                      1373.73(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     17042
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.37
_exptl_crystal_size_mid           0.27
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.637
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              680
_exptl_absorpt_coefficient_mu     0.774
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7626
_exptl_absorpt_correction_T_max   0.9406
_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    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             19825
_diffrn_reflns_av_R_equivalents   0.0476
_diffrn_reflns_av_sigmaI/netI     0.0349
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3152
_reflns_number_gt                 2466
_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.

 Two parts of the molecule are disordered: The fluorines on the CF3 group
 are rotating therefore the fluorine atoms have been left isotropic with
 only two positions modelled for each fluorine atom. The silicon group is
 also disordered with a 180deg rotation where the methylene chloride and
 methyl groups swop over. The position of the silicon group is also
 slightly offset. The occupancies of each disorder assembly were refined.

 To ensure the disorder was not a product of a too high symmetry space
 group being selected, the structure was solved in P1 which also showed
 the same disorder.

 Due to the higher R1 and wR values relative to the Rint, merohedral
 twinning was tested for using ROTAX, however none of the suggested
 matricies lowered the R values. Instead it is assumed that the higher
 R values are a result of the disorder.
;
 
_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)+(0.1264P)²+6.0453P] 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          3152
_refine_ls_number_parameters      202
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1116
_refine_ls_R_factor_gt            0.0947
_refine_ls_wR_factor_ref          0.2635
_refine_ls_wR_factor_gt           0.2496
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.070
_refine_ls_shift/su_max           0.002
_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
C21 C 0.3507(7) 0.3065(11) 0.0431(3) 0.0425(17) Uani 0.806(6) 1 d P A 1
H21A H 0.2490 0.3570 0.0413 0.051 Uiso 0.806(6) 1 calc PR A 1
H21B H 0.3934 0.3635 0.0082 0.051 Uiso 0.806(6) 1 calc PR A 1
C22 C 0.5093(11) 0.5988(10) 0.1451(5) 0.0491(18) Uani 0.806(6) 1 d P A 1
H22A H 0.5578 0.6557 0.1126 0.074 Uiso 0.806(6) 1 calc PR A 1
H22B H 0.5747 0.6101 0.1882 0.074 Uiso 0.806(6) 1 calc PR A 1
H22C H 0.4133 0.6596 0.1451 0.074 Uiso 0.806(6) 1 calc PR A 1
Si1 Si 0.4751(2) 0.3548(3) 0.12512(12) 0.0263(5) Uani 0.806(6) 1 d P A 1
Cl1 Cl 0.2882(5) 0.3208(5) 0.17920(19) 0.0424(7) Uani 0.806(6) 1 d P A 1
Cl2 Cl 0.3409(3) 0.0629(4) 0.03240(12) 0.0837(11) Uani 0.806(6) 1 d P A 1
F8A F 1.0159(13) -0.2659(16) 0.2348(6) 0.095(4) Uiso 0.527(12) 1 d P B 1
F8B F 1.0053(11) -0.3610(12) 0.1342(4) 0.071(3) Uiso 0.527(12) 1 d P B 1
F8C F 1.1738(12) -0.1867(14) 0.1794(6) 0.091(4) Uiso 0.527(12) 1 d P B 1
C21B C 0.445(3) 0.548(4) 0.1069(14) 0.042(6) Uani 0.194(6) 1 d P A 2
H21C H 0.4693 0.5997 0.0668 0.050 Uiso 0.194(6) 1 calc PR A 2
H21D H 0.3452 0.5944 0.1112 0.050 Uiso 0.194(6) 1 calc PR A 2
C22B C 0.333(3) 0.201(5) 0.0302(13) 0.0491(18) Uani 0.194(6) 1 d PD A 2
H22D H 0.3758 0.0825 0.0221 0.074 Uiso 0.194(6) 1 calc PR A 2
H22E H 0.3343 0.2820 -0.0066 0.074 Uiso 0.194(6) 1 calc PR A 2
H22F H 0.2292 0.1839 0.0354 0.074 Uiso 0.194(6) 1 calc PR A 2
Si1B Si 0.4415(10) 0.2980(14) 0.1023(5) 0.030(2) Uani 0.194(6) 1 d PD A 2
Cl1B Cl 0.2668(18) 0.270(2) 0.1636(8) 0.045(3) Uani 0.194(6) 1 d P A 2
Cl2B Cl 0.5849(14) 0.6164(13) 0.1762(5) 0.066(3) Uani 0.194(6) 1 d P A 2
F8D F 0.9536(13) -0.3531(16) 0.2075(5) 0.081(3) Uiso 0.473(12) 1 d P B 2
F8E F 1.0949(18) -0.3025(19) 0.1358(7) 0.104(4) Uiso 0.473(12) 1 d P B 2
F8F F 1.1362(15) -0.1787(17) 0.2243(7) 0.099(4) Uiso 0.473(12) 1 d P B 2
C2 C 0.8050(6) -0.0276(7) 0.1745(2) 0.0357(11) Uani 1 1 d . . .
H2 H 0.7808 -0.1007 0.2082 0.043 Uiso 1 1 calc R . .
C3 C 0.9310(6) -0.0635(8) 0.1516(2) 0.0426(12) Uani 1 1 d . B .
C4 C 0.9679(6) 0.0462(8) 0.1019(2) 0.0393(11) Uani 1 1 d . . .
H4 H 1.0568 0.0235 0.0861 0.047 Uiso 1 1 calc R . .
C5 C 0.8750(5) 0.1838(6) 0.0773(2) 0.0333(10) Uani 1 1 d . . .
C6 C 0.7420(5) 0.2208(6) 0.1007(2) 0.0294(9) Uani 1 1 d . A .
C7 C 0.5753(5) 0.1566(7) 0.1727(2) 0.0342(10) Uani 1 1 d . . .
H7A H 0.6010 0.1882 0.2194 0.041 Uiso 1 1 calc R A 1
H7B H 0.5079 0.0494 0.1675 0.041 Uiso 1 1 calc R A 1
C8 C 1.0275(9) -0.2243(13) 0.1773(3) 0.071(2) Uani 1 1 d . . .
N1 N 0.7134(4) 0.1115(5) 0.14966(18) 0.0286(8) Uani 1 1 d . A .
O6 O 0.6480(4) 0.3455(5) 0.08094(19) 0.0402(9) Uani 1 1 d . . .
Cl5 Cl 0.90832(16) 0.31599(19) 0.01449(8) 0.0485(4) Uani 1 1 d . . .
 
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
C21 0.026(3) 0.067(5) 0.033(3) 0.014(3) 0.002(2) -0.005(3)
C22 0.046(4) 0.035(4) 0.072(6) -0.008(4) 0.026(4) 0.000(3)
Si1 0.0203(9) 0.0300(10) 0.0289(10) -0.0013(8) 0.0058(7) -0.0014(7)
Cl1 0.0336(14) 0.0509(18) 0.0480(17) -0.0056(11) 0.0210(12) -0.0001(11)
Cl2 0.0643(14) 0.103(2) 0.0753(15) -0.0605(15) -0.0062(11) -0.0001(13)
C21B 0.039(14) 0.044(16) 0.040(14) -0.005(13) 0.004(12) 0.000(12)
C22B 0.046(4) 0.035(4) 0.072(6) -0.008(4) 0.026(4) 0.000(3)
Si1B 0.018(4) 0.038(5) 0.035(5) 0.000(4) 0.006(3) -0.002(3)
Cl1B 0.028(5) 0.061(9) 0.051(8) -0.006(5) 0.024(5) -0.008(5)
Cl2B 0.071(7) 0.047(5) 0.075(7) -0.013(4) 0.003(5) -0.013(4)
C2 0.039(3) 0.036(3) 0.030(2) 0.0025(19) 0.0023(19) 0.009(2)
C3 0.043(3) 0.048(3) 0.035(2) 0.001(2) 0.003(2) 0.017(2)
C4 0.032(2) 0.045(3) 0.041(3) -0.008(2) 0.008(2) 0.006(2)
C5 0.031(2) 0.033(2) 0.038(2) -0.0005(19) 0.0109(19) -0.0016(18)
C6 0.026(2) 0.027(2) 0.037(2) 0.0013(18) 0.0090(18) 0.0001(17)
C7 0.024(2) 0.044(3) 0.036(2) 0.008(2) 0.0090(18) 0.0040(19)
C8 0.060(4) 0.111(6) 0.044(3) 0.016(4) 0.013(3) 0.038(4)
N1 0.0243(18) 0.0322(19) 0.0294(18) 0.0011(15) 0.0061(14) 0.0024(15)
O6 0.0289(17) 0.0413(19) 0.055(2) 0.0192(17) 0.0189(16) 0.0085(14)
Cl5 0.0422(8) 0.0450(8) 0.0674(9) 0.0119(6) 0.0325(7) 0.0017(5)
 
_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
C21 Cl2 1.803(9) . ?
C21 Si1 1.892(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 Si1 1.853(9) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Si1 C7 1.891(5) . ?
Si1 O6 1.983(4) . ?
Si1 Cl1 2.243(4) . ?
F8A C8 1.271(12) . ?
F8B C8 1.339(12) . ?
F8C C8 1.349(14) . ?
C21B Cl2B 1.80(3) . ?
C21B Si1B 1.84(3) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B Si1B 1.780(18) . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
Si1B C7 2.003(10) . ?
Si1B O6 2.047(8) . ?
Si1B Cl1B 2.250(17) . ?
F8D C8 1.387(14) . ?
F8E C8 1.299(15) . ?
F8F C8 1.290(14) . ?
C2 N1 1.354(6) . ?
C2 C3 1.355(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(8) . ?
C3 C8 1.504(9) . ?
C4 C5 1.350(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(7) . ?
C5 Cl5 1.714(5) . ?
C6 O6 1.264(6) . ?
C6 N1 1.372(6) . ?
C7 N1 1.472(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
 
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
Cl2 C21 Si1 107.8(3) . . ?
Cl2 C21 H21A 110.2 . . ?
Si1 C21 H21A 110.2 . . ?
Cl2 C21 H21B 110.2 . . ?
Si1 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C22 Si1 C7 125.8(5) . . ?
C22 Si1 C21 115.4(5) . . ?
C7 Si1 C21 118.1(3) . . ?
C22 Si1 O6 91.6(3) . . ?
C7 Si1 O6 83.06(19) . . ?
C21 Si1 O6 87.1(3) . . ?
C22 Si1 Cl1 95.8(3) . . ?
C7 Si1 Cl1 88.81(19) . . ?
C21 Si1 Cl1 93.9(2) . . ?
O6 Si1 Cl1 171.24(18) . . ?
Cl2B C21B Si1B 108.9(16) . . ?
Cl2B C21B H21C 109.9 . . ?
Si1B C21B H21C 109.9 . . ?
Cl2B C21B H21D 109.9 . . ?
Si1B C21B H21D 109.9 . . ?
H21C C21B H21D 108.3 . . ?
Si1B C22B H22D 109.5 . . ?
Si1B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
Si1B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C22B Si1B C21B 116.6(16) . . ?
C22B Si1B C7 124.6(13) . . ?
C21B Si1B C7 118.5(11) . . ?
C22B Si1B O6 104.8(12) . . ?
C21B Si1B O6 80.5(10) . . ?
C7 Si1B O6 78.7(3) . . ?
C22B Si1B Cl1B 96.8(12) . . ?
C21B Si1B Cl1B 93.9(11) . . ?
C7 Si1B Cl1B 85.5(6) . . ?
O6 Si1B Cl1B 158.0(7) . . ?
N1 C2 C3 120.5(5) . . ?
N1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 C8 119.8(5) . . ?
C4 C3 C8 120.4(5) . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 Cl5 121.7(4) . . ?
C6 C5 Cl5 117.0(4) . . ?
O6 C6 N1 116.8(4) . . ?
O6 C6 C5 126.2(4) . . ?
N1 C6 C5 116.9(4) . . ?
N1 C7 Si1 110.5(3) . . ?
N1 C7 Si1B 107.7(4) . . ?
Si1 C7 Si1B 19.3(3) . . ?
N1 C7 H7A 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1B C7 H7A 126.6 . . ?
N1 C7 H7B 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
Si1B C7 H7B 93.6 . . ?
H7A C7 H7B 108.1 . . ?
F8A C8 F8F 62.3(8) . . ?
F8A C8 F8E 132.4(10) . . ?
F8F C8 F8E 103.7(10) . . ?
F8A C8 F8B 115.6(10) . . ?
F8F C8 F8B 134.3(9) . . ?
F8E C8 F8B 40.6(7) . . ?
F8A C8 F8C 106.9(9) . . ?
F8F C8 F8C 47.7(7) . . ?
F8E C8 F8C 61.0(8) . . ?
F8B C8 F8C 100.8(8) . . ?
F8A C8 F8D 42.2(6) . . ?
F8F C8 F8D 101.2(9) . . ?
F8E C8 F8D 110.1(11) . . ?
F8B C8 F8D 77.1(8) . . ?
F8C C8 F8D 133.7(8) . . ?
F8A C8 C3 112.0(8) . . ?
F8F C8 C3 111.7(9) . . ?
F8E C8 C3 115.2(8) . . ?
F8B C8 C3 110.4(6) . . ?
F8C C8 C3 110.4(8) . . ?
F8D C8 C3 113.5(7) . . ?
C2 N1 C6 122.3(4) . . ?
C2 N1 C7 122.8(4) . . ?
C6 N1 C7 114.8(4) . . ?
C6 O6 Si1 114.7(3) . . ?
C6 O6 Si1B 113.1(4) . . ?
Si1 O6 Si1B 18.8(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    1.677
_refine_diff_density_min   -0.906
_refine_diff_density_rms    0.135
