 
data_2009src0138
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H15 Cl N2 O2 Si'
_chemical_formula_weight          294.81
 
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'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    Pbca
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    11.8719(3)
_cell_length_b                    15.0801(3)
_cell_length_c                    15.5429(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2782.64(10)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     22095
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.23
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.407
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1232
_exptl_absorpt_coefficient_mu     0.360
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8875
_exptl_absorpt_correction_T_max   0.9514
_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             32004
_diffrn_reflns_av_R_equivalents   0.0758
_diffrn_reflns_av_sigmaI/netI     0.0426
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3187
_reflns_number_gt                 2496
_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.
;
 
_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)+(0.0566P)²+1.1873P] 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          3187
_refine_ls_number_parameters      174
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0598
_refine_ls_R_factor_gt            0.0414
_refine_ls_wR_factor_ref          0.1105
_refine_ls_wR_factor_gt           0.1006
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_restrained_S_all       1.052
_refine_ls_shift/su_max           0.009
_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
C2 C 0.27974(17) -0.07469(13) 0.67558(12) 0.0200(4) Uani 1 1 d . . .
C3 C 0.26888(18) -0.12810(13) 0.59942(13) 0.0237(4) Uani 1 1 d . . .
H3 H 0.1989 -0.1561 0.5875 0.028 Uiso 1 1 calc R . .
C4 C 0.35585(19) -0.13946(13) 0.54435(12) 0.0230(4) Uani 1 1 d . . .
H4 H 0.3451 -0.1734 0.4935 0.028 Uiso 1 1 calc R . .
C5 C 0.46215(18) -0.10174(13) 0.56113(12) 0.0244(4) Uani 1 1 d . . .
H5 H 0.5231 -0.1104 0.5225 0.029 Uiso 1 1 calc R . .
C6 C 0.47578(17) -0.05291(13) 0.63336(12) 0.0223(4) Uani 1 1 d . . .
H6 H 0.5472 -0.0274 0.6456 0.027 Uiso 1 1 calc R . .
C7 C 0.40358(16) 0.01776(12) 0.76421(11) 0.0176(4) Uani 1 1 d . . .
H7 H 0.4838 0.0380 0.7635 0.021 Uiso 1 1 calc R . .
C9 C 0.45063(17) -0.10917(13) 0.86060(12) 0.0215(4) Uani 1 1 d . . .
H9 H 0.5097 -0.1262 0.8228 0.026 Uiso 1 1 calc R . .
C10 C 0.42857(19) -0.15823(14) 0.93226(13) 0.0254(4) Uani 1 1 d . . .
H10 H 0.4722 -0.2093 0.9453 0.030 Uiso 1 1 calc R . .
C11 C 0.33966(19) -0.13176(13) 0.98660(13) 0.0255(5) Uani 1 1 d . . .
H11 H 0.3227 -0.1661 1.0362 0.031 Uiso 1 1 calc R . .
C12 C 0.27775(18) -0.05805(13) 0.96932(12) 0.0226(4) Uani 1 1 d . . .
H12 H 0.2180 -0.0410 1.0065 0.027 Uiso 1 1 calc R . .
C13 C 0.30322(16) -0.00709(12) 0.89554(12) 0.0194(4) Uani 1 1 d . . .
C15 C 0.38165(19) 0.21194(14) 0.83952(13) 0.0276(5) Uani 1 1 d . . .
H15A H 0.3847 0.2665 0.8053 0.041 Uiso 1 1 calc R . .
H15B H 0.4584 0.1931 0.8539 0.041 Uiso 1 1 calc R . .
H15C H 0.3394 0.2229 0.8926 0.041 Uiso 1 1 calc R . .
C16 C 0.16806(17) 0.15164(14) 0.73475(13) 0.0242(4) Uani 1 1 d . . .
H16A H 0.1137 0.1501 0.7822 0.036 Uiso 1 1 calc R . .
H16B H 0.1458 0.1088 0.6905 0.036 Uiso 1 1 calc R . .
H16C H 0.1697 0.2113 0.7098 0.036 Uiso 1 1 calc R . .
N1 N 0.38745(13) -0.03964(10) 0.68938(9) 0.0177(3) Uani 1 1 d . . .
N8 N 0.38774(13) -0.03551(11) 0.84324(10) 0.0181(3) Uani 1 1 d . . .
O2 O 0.20325(12) -0.05772(10) 0.72769(8) 0.0253(3) Uani 1 1 d . . .
O13 O 0.25201(12) 0.06473(9) 0.87374(8) 0.0224(3) Uani 1 1 d . . .
Si14 Si 0.31014(4) 0.12283(3) 0.77602(3) 0.01809(15) Uani 1 1 d . . .
Cl17 Cl 0.39042(4) 0.16615(3) 0.64351(3) 0.02143(14) 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
C2 O2 1.243(2) . ?
C2 N1 1.400(3) . ?
C2 C3 1.438(3) . ?
C3 C4 1.352(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.352(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.378(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.462(2) . ?
C7 N8 1.480(2) . ?
C7 Si14 1.943(2) . ?
C7 H7 1.0000 . ?
C9 C10 1.363(3) . ?
C9 N8 1.365(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.410(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.359(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(3) . ?
C12 H12 0.9500 . ?
C13 O13 1.287(2) . ?
C13 N8 1.361(2) . ?
C15 Si14 1.871(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 Si14 1.856(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O13 Si14 1.8844(14) . ?
Si14 Cl17 2.3615(7) . ?
 
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
O2 C2 N1 119.30(17) . . ?
O2 C2 C3 125.89(19) . . ?
N1 C2 C3 114.80(17) . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.05(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.74(19) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 N1 120.85(19) . . ?
C5 C6 H6 119.6 . . ?
N1 C6 H6 119.6 . . ?
N1 C7 N8 108.80(15) . . ?
N1 C7 Si14 118.89(13) . . ?
N8 C7 Si14 106.97(12) . . ?
N1 C7 H7 107.2 . . ?
N8 C7 H7 107.2 . . ?
Si14 C7 H7 107.2 . . ?
C10 C9 N8 119.89(18) . . ?
C10 C9 H9 120.1 . . ?
N8 C9 H9 120.1 . . ?
C9 C10 C11 118.68(19) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 121.21(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.30(18) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
O13 C13 N8 117.13(16) . . ?
O13 C13 C12 124.76(17) . . ?
N8 C13 C12 118.12(17) . . ?
Si14 C15 H15A 109.5 . . ?
Si14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si14 C16 H16A 109.5 . . ?
Si14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 N1 C2 122.93(16) . . ?
C6 N1 C7 119.28(16) . . ?
C2 N1 C7 117.70(15) . . ?
C13 N8 C9 122.78(16) . . ?
C13 N8 C7 114.75(15) . . ?
C9 N8 C7 122.43(15) . . ?
C13 O13 Si14 115.49(12) . . ?
C16 Si14 C15 115.25(10) . . ?
C16 Si14 O13 93.13(8) . . ?
C15 Si14 O13 94.29(8) . . ?
C16 Si14 C7 132.62(9) . . ?
C15 Si14 C7 112.12(9) . . ?
O13 Si14 C7 84.61(7) . . ?
C16 Si14 Cl17 90.04(7) . . ?
C15 Si14 Cl17 94.49(7) . . ?
O13 Si14 Cl17 168.35(5) . . ?
C7 Si14 Cl17 85.00(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.276
_refine_diff_density_min   -0.398
_refine_diff_density_rms    0.069
