data_2008src0940
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H12 Cl F N O2 Si'
_chemical_formula_weight          236.73
 
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'
 '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'
 '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
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.2306(5)
_cell_length_b                    9.4023(8)
_cell_length_c                    9.5351(8)
_cell_angle_alpha                 119.096(4)
_cell_angle_beta                  96.715(5)
_cell_angle_gamma                 98.833(5)
_cell_volume                      545.76(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     32799
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.36
_exptl_crystal_size_mid           0.26
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.441
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              246
_exptl_absorpt_coefficient_mu     0.448
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8552
_exptl_absorpt_correction_T_max   0.9650
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_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 KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             12277
_diffrn_reflns_av_R_equivalents   0.0571
_diffrn_reflns_av_sigmaI/netI     0.0445
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.50
_reflns_number_total              2511
_reflns_number_gt                 2001
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'Sheldrick, G.M. (2008). Acta Cryst. A64, 112-1'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_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 > 2sigma(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)+(0.1212P)²+1.8567P] 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          2511
_refine_ls_number_parameters      129
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1003
_refine_ls_R_factor_gt            0.0826
_refine_ls_wR_factor_ref          0.2356
_refine_ls_wR_factor_gt           0.2210
_refine_ls_goodness_of_fit_ref    1.064
_refine_ls_restrained_S_all       1.064
_refine_ls_shift/su_max           0.004
_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
Si1 Si 0.30912(18) 0.20526(14) 0.70990(13) 0.0280(3) Uani 1 1 d . . .
Cl1 Cl 0.59182(18) 0.38007(15) 0.59502(15) 0.0403(4) Uani 1 1 d . . .
O1 O 0.3977(4) 0.2652(3) 0.9408(3) 0.0259(6) Uani 1 1 d . . .
N1 N 0.2322(5) -0.0022(4) 0.8380(4) 0.0215(7) Uani 1 1 d . . .
C1 C 0.2142(6) -0.0076(5) 0.6801(5) 0.0258(8) Uani 1 1 d . . .
H1A H 0.0774 -0.0500 0.6219 0.031 Uiso 1 1 calc R . .
H1B H 0.2859 -0.0866 0.6105 0.031 Uiso 1 1 calc R . .
C5 C 0.1845(6) -0.1186(6) 1.0046(5) 0.0279(9) Uani 1 1 d . . .
H5 H 0.1339 -0.2101 1.0171 0.033 Uiso 1 1 calc R . .
C6 C 0.1550(6) -0.1362(5) 0.8519(5) 0.0245(8) Uani 1 1 d . . .
C2 C 0.3351(5) 0.1495(5) 0.9697(5) 0.0217(8) Uani 1 1 d . . .
C4 C 0.2897(6) 0.0352(6) 1.1432(5) 0.0279(9) Uani 1 1 d . . .
H4 H 0.3084 0.0467 1.2488 0.033 Uiso 1 1 calc R . .
C3 C 0.3651(6) 0.1675(5) 1.1278(5) 0.0251(8) Uani 1 1 d . . .
H3 H 0.4369 0.2705 1.2217 0.030 Uiso 1 1 calc R . .
C8 C 0.5677(7) 0.2929(6) 0.7267(6) 0.0371(10) Uani 1 1 d . . .
H8B H 0.6270 0.3815 0.8423 0.045 Uiso 1 1 calc R . .
H8A H 0.6373 0.2027 0.6955 0.045 Uiso 1 1 calc R . .
F1 F 0.2425(4) 0.1226(4) 0.5056(3) 0.0378(7) Uani 1 1 d . . .
C7 C 0.0458(7) -0.2947(5) 0.6976(5) 0.0310(9) Uani 1 1 d . . .
H7A H -0.0613 -0.2719 0.6451 0.037 Uiso 1 1 calc R . .
H7C H -0.0040 -0.3791 0.7247 0.037 Uiso 1 1 calc R . .
H7B H 0.1313 -0.3366 0.6219 0.037 Uiso 1 1 calc R . .
C9 C 0.1528(9) 0.3598(7) 0.7770(7) 0.0464(13) Uani 1 1 d . . .
H9A H 0.0783 0.3523 0.6800 0.070 Uiso 1 1 calc R . .
H9B H 0.2339 0.4737 0.8491 0.070 Uiso 1 1 calc R . .
H9C H 0.0653 0.3336 0.8368 0.070 Uiso 1 1 calc R . .
 
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
Si1 0.0408(7) 0.0253(6) 0.0185(6) 0.0127(5) 0.0031(5) 0.0073(5)
Cl1 0.0503(7) 0.0355(6) 0.0410(7) 0.0225(5) 0.0193(5) 0.0089(5)
O1 0.0346(15) 0.0222(14) 0.0186(13) 0.0103(11) 0.0014(11) 0.0046(11)
N1 0.0251(16) 0.0248(16) 0.0171(15) 0.0118(13) 0.0042(12) 0.0093(13)
C1 0.032(2) 0.027(2) 0.0158(17) 0.0104(16) 0.0024(15) 0.0058(16)
C5 0.027(2) 0.034(2) 0.035(2) 0.0236(19) 0.0120(17) 0.0136(17)
C6 0.0234(18) 0.027(2) 0.028(2) 0.0156(17) 0.0094(16) 0.0117(16)
C2 0.0220(18) 0.028(2) 0.0180(17) 0.0124(15) 0.0061(14) 0.0110(15)
C4 0.028(2) 0.042(2) 0.0242(19) 0.0207(19) 0.0103(16) 0.0185(18)
C3 0.0261(19) 0.032(2) 0.0171(17) 0.0115(16) 0.0042(14) 0.0112(16)
C8 0.041(2) 0.039(3) 0.029(2) 0.021(2) 0.0031(19) -0.003(2)
F1 0.0505(16) 0.0406(15) 0.0203(12) 0.0175(11) 0.0016(11) 0.0038(12)
C7 0.035(2) 0.026(2) 0.031(2) 0.0130(18) 0.0092(18) 0.0089(17)
C9 0.065(3) 0.039(3) 0.040(3) 0.024(2) 0.000(2) 0.019(3)
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
Si1 F1 1.680(3) . ?
Si1 C8 1.879(5) . ?
Si1 C1 1.881(4) . ?
Si1 C9 1.889(6) . ?
Si1 O1 1.981(3) . ?
Cl1 C8 1.813(5) . ?
O1 C2 1.279(5) . ?
N1 C2 1.371(5) . ?
N1 C6 1.371(5) . ?
N1 C1 1.471(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C5 C6 1.369(6) . ?
C5 C4 1.408(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.498(6) . ?
C2 C3 1.418(5) . ?
C4 C3 1.362(6) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 Si1 C8 95.31(18) . . ?
F1 Si1 C1 89.40(16) . . ?
C8 Si1 C1 123.9(2) . . ?
F1 Si1 C9 98.37(19) . . ?
C8 Si1 C9 116.4(3) . . ?
C1 Si1 C9 118.1(2) . . ?
F1 Si1 O1 170.17(15) . . ?
C8 Si1 O1 84.56(17) . . ?
C1 Si1 O1 82.58(14) . . ?
C9 Si1 O1 90.45(19) . . ?
C2 O1 Si1 114.1(2) . . ?
C2 N1 C6 123.3(3) . . ?
C2 N1 C1 113.4(3) . . ?
C6 N1 C1 123.3(3) . . ?
N1 C1 Si1 111.7(3) . . ?
N1 C1 H1A 109.3 . . ?
Si1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
Si1 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 N1 118.4(4) . . ?
C5 C6 C7 123.9(4) . . ?
N1 C6 C7 117.6(4) . . ?
O1 C2 N1 117.3(3) . . ?
O1 C2 C3 124.6(4) . . ?
N1 C2 C3 118.1(4) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
Cl1 C8 Si1 111.6(3) . . ?
Cl1 C8 H8B 109.3 . . ?
Si1 C8 H8B 109.3 . . ?
Cl1 C8 H8A 109.3 . . ?
Si1 C8 H8A 109.3 . . ?
H8B C8 H8A 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    2.752
_refine_diff_density_min   -0.706
_refine_diff_density_rms    0.131

