 
data_2007src0238

_audit_creation_method            SHELXL-97

# The Flack parameter for this structure is 0.06 (12) whereas that for the 
# inverted structure is 0.91 (12). We are thus satisfied that the absolute 
# structure has been determined correctly for this structure. The absolute 
# configuration of atom C4 is S.

_chemical_name_systematic
;
      Dr P. G. Taylor
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H21 N O2 Si'
_chemical_formula_weight          251.40

 
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'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    'P 2(1)2(1)2(1)'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    7.23190(10)
_cell_length_b                    11.0720(3)
_cell_length_c                    18.1646(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1454.47(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11225
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.34
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.148
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              544
_exptl_absorpt_coefficient_mu     0.153
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9412
_exptl_absorpt_correction_T_max   0.9497
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 SADABS was used to perform the Absorption correction
Parameter refinement on 15873 reflections reduced R(int) from 0.0652 to 0.0338
Ratio of minimum to maximum apparent transmission: 0.837440
The given Tmin and Tmax were generated using the SHELX SIZE command.
;

 
_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 95mm 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             17363
_diffrn_reflns_av_R_equivalents   0.0369
_diffrn_reflns_av_sigmaI/netI     0.0292
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.03
_diffrn_reflns_theta_max          27.47
_reflns_number_total              3314
_reflns_number_gt                 3142
_reflns_threshold_expression      >2sigma(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    
;
Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., 
Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 
2004)
;
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     
'PLATON/PLUTON (Spek, A. L., 1998)'
_computing_publication_material   'WinGX (Farrugia, 1999)'

 
_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)+(0.0688P)²+0.0365P] 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        0.212(11)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.06(12)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          3314
_refine_ls_number_parameters      160
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0492
_refine_ls_R_factor_gt            0.0457
_refine_ls_wR_factor_ref          0.1123
_refine_ls_wR_factor_gt           0.1094
_refine_ls_goodness_of_fit_ref    1.261
_refine_ls_restrained_S_all       1.261
_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 0.0725(3) 0.1554(2) 0.09657(11) 0.0356(5) Uani 1 1 d . . .
H1A H 0.0742 0.0747 0.1187 0.053 Uiso 1 1 calc R . .
H1B H 0.0798 0.1482 0.0429 0.053 Uiso 1 1 calc R . .
H1C H -0.0424 0.1968 0.1101 0.053 Uiso 1 1 calc R . .
C2 C 0.2726(3) 0.39824(16) 0.09076(9) 0.0324(4) Uani 1 1 d . . .
H2A H 0.1541 0.4374 0.1015 0.049 Uiso 1 1 calc R . .
H2B H 0.2895 0.3930 0.0373 0.049 Uiso 1 1 calc R . .
H2C H 0.3734 0.4457 0.1123 0.049 Uiso 1 1 calc R . .
C3 C 0.4989(3) 0.17115(18) 0.10622(11) 0.0355(4) Uani 1 1 d . . .
H3A H 0.6010 0.2186 0.1267 0.053 Uiso 1 1 calc R . .
H3B H 0.5109 0.1675 0.0525 0.053 Uiso 1 1 calc R . .
H3C H 0.5025 0.0892 0.1265 0.053 Uiso 1 1 calc R . .
C4 C 0.1153(2) 0.22286(13) 0.26804(8) 0.0179(3) Uani 1 1 d . . .
H4 H 0.0603 0.1428 0.2550 0.021 Uiso 1 1 calc R . .
C5 C -0.0308(2) 0.32249(14) 0.25956(9) 0.0201(3) Uani 1 1 d . . .
C6 C -0.3411(3) 0.39388(16) 0.28244(12) 0.0346(4) Uani 1 1 d . . .
H6A H -0.2895 0.4659 0.2587 0.052 Uiso 1 1 calc R . .
H6B H -0.3719 0.4125 0.3337 0.052 Uiso 1 1 calc R . .
H6C H -0.4532 0.3687 0.2563 0.052 Uiso 1 1 calc R . .
C7 C -0.2704(2) 0.18035(15) 0.30873(10) 0.0267(4) Uani 1 1 d . . .
H7A H -0.1849 0.1165 0.2933 0.040 Uiso 1 1 calc R . .
H7B H -0.3940 0.1633 0.2893 0.040 Uiso 1 1 calc R . .
H7C H -0.2754 0.1834 0.3626 0.040 Uiso 1 1 calc R . .
C8 C 0.1848(2) 0.22052(15) 0.34737(8) 0.0199(3) Uani 1 1 d . . .
C9 C 0.2418(2) 0.32681(15) 0.38169(9) 0.0267(4) Uani 1 1 d . . .
H9 H 0.2295 0.4019 0.3568 0.032 Uiso 1 1 calc R . .
C10 C 0.3163(3) 0.3233(2) 0.45189(11) 0.0349(4) Uani 1 1 d . . .
H10 H 0.3561 0.3959 0.4749 0.042 Uiso 1 1 calc R . .
C11 C 0.3329(3) 0.2146(2) 0.48856(10) 0.0404(5) Uani 1 1 d . . .
H11 H 0.3856 0.2122 0.5364 0.048 Uiso 1 1 calc R . .
C12 C 0.2727(3) 0.1092(2) 0.45565(10) 0.0377(4) Uani 1 1 d . . .
H12 H 0.2814 0.0348 0.4814 0.045 Uiso 1 1 calc R . .
C13 C 0.1992(3) 0.11172(16) 0.38476(9) 0.0269(4) Uani 1 1 d . . .
H13 H 0.1590 0.0390 0.3621 0.032 Uiso 1 1 calc R . .
N1 N -0.20585(18) 0.29683(12) 0.28033(8) 0.0218(3) Uani 1 1 d . . .
O1 O 0.27070(14) 0.24682(10) 0.22191(6) 0.0209(2) Uani 1 1 d . . .
O2 O 0.01373(18) 0.42226(11) 0.23607(7) 0.0310(3) Uani 1 1 d . . .
Si1 Si 0.27398(6) 0.24404(4) 0.13081(2) 0.02088(15) 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
C1 0.0372(10) 0.0444(11) 0.0253(9) -0.0074(8) -0.0048(8) -0.0033(8)
C2 0.0412(11) 0.0293(9) 0.0267(8) 0.0035(7) 0.0082(8) 0.0063(8)
C3 0.0334(10) 0.0388(10) 0.0342(10) 0.0050(8) 0.0141(9) 0.0105(8)
C4 0.0164(7) 0.0199(8) 0.0173(7) -0.0007(6) 0.0021(5) -0.0016(6)
C5 0.0184(8) 0.0215(8) 0.0202(8) 0.0021(6) 0.0003(6) -0.0020(6)
C6 0.0191(8) 0.0252(9) 0.0596(12) -0.0017(9) 0.0038(8) 0.0010(7)
C7 0.0219(8) 0.0239(8) 0.0344(9) 0.0024(6) 0.0040(7) -0.0050(7)
C8 0.0146(7) 0.0277(8) 0.0175(7) -0.0017(6) 0.0025(5) 0.0011(6)
C9 0.0200(8) 0.0316(8) 0.0285(8) -0.0071(7) 0.0034(7) -0.0031(6)
C10 0.0236(9) 0.0521(12) 0.0291(9) -0.0155(8) -0.0002(7) -0.0035(8)
C11 0.0260(9) 0.0743(15) 0.0209(8) -0.0068(9) -0.0048(7) 0.0078(9)
C12 0.0375(10) 0.0492(11) 0.0265(9) 0.0093(8) -0.0016(8) 0.0131(9)
C13 0.0286(9) 0.0281(8) 0.0240(8) 0.0013(7) -0.0002(6) 0.0033(7)
N1 0.0164(6) 0.0196(6) 0.0295(7) 0.0022(6) 0.0015(5) -0.0007(5)
O1 0.0169(5) 0.0285(6) 0.0173(5) 0.0001(4) 0.0030(4) -0.0015(5)
O2 0.0247(6) 0.0212(6) 0.0470(8) 0.0106(5) 0.0059(6) -0.0012(5)
Si1 0.0222(2) 0.0229(2) 0.0175(2) -0.00042(16) 0.00309(14) 0.00241(17)
 
_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
C1 Si1 1.864(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Si1 1.8559(18) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 Si1 1.8697(19) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.4266(17) . ?
C4 C8 1.526(2) . ?
C4 C5 1.535(2) . ?
C4 H4 1.0000 . ?
C5 O2 1.227(2) . ?
C5 N1 1.351(2) . ?
C6 N1 1.454(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N1 1.465(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.387(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1 Si1 1.6553(11) . ?
 
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
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 C8 107.36(12) . . ?
O1 C4 C5 110.46(11) . . ?
C8 C4 C5 109.48(12) . . ?
O1 C4 H4 109.8 . . ?
C8 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
O2 C5 N1 122.14(15) . . ?
O2 C5 C4 120.09(14) . . ?
N1 C5 C4 117.75(13) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.47(14) . . ?
C13 C8 C4 120.13(14) . . ?
C9 C8 C4 120.34(14) . . ?
C10 C9 C8 120.21(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.15(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.00(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.24(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.90(16) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C5 N1 C6 118.85(14) . . ?
C5 N1 C7 125.57(14) . . ?
C6 N1 C7 115.28(14) . . ?
C4 O1 Si1 126.51(9) . . ?
O1 Si1 C2 112.01(7) . . ?
O1 Si1 C1 109.41(7) . . ?
C2 Si1 C1 110.44(10) . . ?
O1 Si1 C3 105.03(8) . . ?
C2 Si1 C3 107.95(9) . . ?
C1 Si1 C3 111.91(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.555
_refine_diff_density_min   -0.985
_refine_diff_density_rms    0.235
