 
data_2009src0289
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H13 Cl2 N4 O6 Si'
_chemical_formula_weight          420.26
 
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            monoclinic
_symmetry_space_group_name_H-M    P21/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.2948(3)
_cell_length_b                    12.6066(4)
_cell_length_c                    14.3449(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.010(2)
_cell_angle_gamma                 90.00
_cell_volume                      1760.18(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     19456
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        fragment
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.586
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              860
_exptl_absorpt_coefficient_mu     0.477
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9450
_exptl_absorpt_correction_T_max   0.9720
_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             30059
_diffrn_reflns_av_R_equivalents   0.0687
_diffrn_reflns_av_sigmaI/netI     0.0505
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4039
_reflns_number_gt                 3273
_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)+(0.0304P)²+2.1198P] 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          4039
_refine_ls_number_parameters      236
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0622
_refine_ls_R_factor_gt            0.0445
_refine_ls_wR_factor_ref          0.0987
_refine_ls_wR_factor_gt           0.0910
_refine_ls_goodness_of_fit_ref    1.021
_refine_ls_restrained_S_all       1.021
_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
C2 C 0.4880(2) 0.35086(17) -0.23654(16) 0.0166(5) Uani 1 1 d . . .
H2 H 0.5831 0.3586 -0.2011 0.020 Uiso 1 1 calc R . .
C3 C 0.4390(2) 0.36441(17) -0.33615(16) 0.0158(4) Uani 1 1 d . . .
C4 C 0.2986(2) 0.35628(17) -0.39038(16) 0.0164(5) Uani 1 1 d . . .
H4 H 0.2668 0.3657 -0.4599 0.020 Uiso 1 1 calc R . .
C5 C 0.2089(2) 0.33447(17) -0.34069(16) 0.0162(4) Uani 1 1 d . . .
H5 H 0.1130 0.3314 -0.3750 0.019 Uiso 1 1 calc R . .
C6 C 0.2595(2) 0.31658(17) -0.23861(16) 0.0141(4) Uani 1 1 d . . .
C7 C 0.4381(2) 0.31047(19) -0.08106(15) 0.0174(5) Uani 1 1 d . . .
H7A H 0.4679 0.3786 -0.0463 0.021 Uiso 1 1 calc R . .
H7B H 0.5149 0.2592 -0.0587 0.021 Uiso 1 1 calc R . .
C22 C 0.1288(2) 0.40338(17) 0.13905(16) 0.0160(5) Uani 1 1 d . . .
H22 H 0.0500 0.4441 0.1049 0.019 Uiso 1 1 calc R . .
C23 C 0.1728(2) 0.39661(18) 0.23959(16) 0.0165(5) Uani 1 1 d . . .
C24 C 0.2894(2) 0.33779(19) 0.29143(16) 0.0189(5) Uani 1 1 d . . .
H24 H 0.3170 0.3322 0.3612 0.023 Uiso 1 1 calc R . .
C25 C 0.3630(2) 0.28860(19) 0.23991(16) 0.0213(5) Uani 1 1 d . . .
H25 H 0.4441 0.2503 0.2738 0.026 Uiso 1 1 calc R . .
C26 C 0.3176(2) 0.29505(17) 0.13608(15) 0.0152(4) Uani 1 1 d . . .
C27 C 0.1588(2) 0.34903(18) -0.01951(15) 0.0149(4) Uani 1 1 d . . .
H27A H 0.1637 0.4214 -0.0449 0.018 Uiso 1 1 calc R . .
H27B H 0.0633 0.3230 -0.0479 0.018 Uiso 1 1 calc R . .
C31 C 0.2513(3) 0.11292(18) -0.07125(17) 0.0223(5) Uani 1 1 d . . .
H31A H 0.1530 0.0993 -0.1024 0.033 Uiso 1 1 calc R . .
H31B H 0.2835 0.0779 -0.0068 0.033 Uiso 1 1 calc R . .
H31C H 0.3019 0.0850 -0.1132 0.033 Uiso 1 1 calc R . .
N1 N 0.39715(18) 0.32593(14) -0.18945(13) 0.0143(4) Uani 1 1 d . . .
N3 N 0.5370(2) 0.38661(16) -0.38784(14) 0.0201(4) Uani 1 1 d . . .
N21 N 0.20027(18) 0.35056(14) 0.08933(13) 0.0144(4) Uani 1 1 d . . .
N23 N 0.0925(2) 0.45159(16) 0.29235(13) 0.0200(4) Uani 1 1 d . . .
O3A O 0.65712(18) 0.40472(15) -0.33866(13) 0.0288(4) Uani 1 1 d . . .
O3B O 0.49433(19) 0.38485(17) -0.47808(12) 0.0344(5) Uani 1 1 d . . .
O6 O 0.18439(15) 0.29007(12) -0.18660(11) 0.0157(3) Uani 1 1 d . . .
O23A O 0.10644(18) 0.42086(15) 0.37676(12) 0.0282(4) Uani 1 1 d . . .
O23B O 0.01718(18) 0.52374(15) 0.25043(12) 0.0295(4) Uani 1 1 d . . .
O26 O 0.37730(16) 0.25056(13) 0.08047(11) 0.0186(3) Uani 1 1 d . . .
Si1 Si 0.28085(6) 0.25761(5) -0.05486(4) 0.01416(14) Uani 1 1 d . . .
Cl2 Cl 0.20038(6) 0.62973(5) 0.03160(4) 0.02275(14) Uani 1 1 d . . .
Cl1 Cl 0.68849(8) 0.42893(5) 0.14668(5) 0.03360(17) 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 N1 1.357(3) . ?
C2 C3 1.362(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(3) . ?
C3 N3 1.461(3) . ?
C4 C5 1.365(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9500 . ?
C6 O6 1.282(3) . ?
C6 N1 1.367(3) . ?
C7 N1 1.485(3) . ?
C7 Si1 1.898(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C22 N21 1.355(3) . ?
C22 C23 1.366(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(3) . ?
C23 N23 1.465(3) . ?
C24 C25 1.367(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.411(3) . ?
C25 H25 0.9500 . ?
C26 O26 1.284(3) . ?
C26 N21 1.368(3) . ?
C27 N21 1.479(3) . ?
C27 Si1 1.892(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 Si1 1.851(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
N3 O3B 1.224(2) . ?
N3 O3A 1.229(3) . ?
N23 O23B 1.219(3) . ?
N23 O23A 1.234(2) . ?
O6 Si1 1.8713(16) . ?
O26 Si1 1.8727(16) . ?
 
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
N1 C2 C3 118.1(2) . . ?
N1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 N3 118.4(2) . . ?
C4 C3 N3 119.30(19) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
O6 C6 N1 116.29(19) . . ?
O6 C6 C5 124.1(2) . . ?
N1 C6 C5 119.63(19) . . ?
N1 C7 Si1 106.49(14) . . ?
N1 C7 H7A 110.4 . . ?
Si1 C7 H7A 110.4 . . ?
N1 C7 H7B 110.4 . . ?
Si1 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
N21 C22 C23 118.3(2) . . ?
N21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 N23 117.8(2) . . ?
C24 C23 N23 120.45(19) . . ?
C25 C24 C23 118.9(2) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 119.6(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
O26 C26 N21 116.36(18) . . ?
O26 C26 C25 124.8(2) . . ?
N21 C26 C25 118.87(19) . . ?
N21 C27 Si1 107.61(14) . . ?
N21 C27 H27A 110.2 . . ?
Si1 C27 H27A 110.2 . . ?
N21 C27 H27B 110.2 . . ?
Si1 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
Si1 C31 H31A 109.5 . . ?
Si1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
Si1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C2 N1 C6 122.00(18) . . ?
C2 N1 C7 123.02(18) . . ?
C6 N1 C7 114.95(17) . . ?
O3B N3 O3A 123.91(19) . . ?
O3B N3 C3 117.63(19) . . ?
O3A N3 C3 118.45(18) . . ?
C22 N21 C26 122.53(18) . . ?
C22 N21 C27 122.87(18) . . ?
C26 N21 C27 114.59(17) . . ?
O23B N23 O23A 124.77(19) . . ?
O23B N23 C23 118.27(18) . . ?
O23A N23 C23 116.96(19) . . ?
C6 O6 Si1 115.00(14) . . ?
C26 O26 Si1 115.08(14) . . ?
C31 Si1 O6 94.36(9) . . ?
C31 Si1 O26 95.42(9) . . ?
O6 Si1 O26 170.06(8) . . ?
C31 Si1 C27 122.57(11) . . ?
O6 Si1 C27 87.54(8) . . ?
O26 Si1 C27 85.71(8) . . ?
C31 Si1 C7 115.85(11) . . ?
O6 Si1 C7 85.96(8) . . ?
O26 Si1 C7 91.35(8) . . ?
C27 Si1 C7 121.53(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.516
_refine_diff_density_min   -0.346
_refine_diff_density_rms    0.071
