data_2008src1016
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H15 Cl5 N2 O2 Si'
_chemical_formula_weight          448.62
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.6668(2)
_cell_length_b                    10.8424(4)
_cell_length_c                    12.6410(5)
_cell_angle_alpha                 79.319(2)
_cell_angle_beta                  73.438(2)
_cell_angle_gamma                 73.223(2)
_cell_volume                      958.24(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     24844
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.55
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.555
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              456
_exptl_absorpt_coefficient_mu     0.830
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6583
_exptl_absorpt_correction_T_max   0.8516
_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             19471
_diffrn_reflns_av_R_equivalents   0.0413
_diffrn_reflns_av_sigmaI/netI     0.0369
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.50
_reflns_number_total              4386
_reflns_number_gt                 3655
_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)+(0.0443P)²+0.9920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4386
_refine_ls_number_parameters      222
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0504
_refine_ls_R_factor_gt            0.0383
_refine_ls_wR_factor_ref          0.0992
_refine_ls_wR_factor_gt           0.0932
_refine_ls_goodness_of_fit_ref    1.025
_refine_ls_restrained_S_all       1.025
_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
C1 C -0.0800(3) 0.7749(2) -0.31370(17) 0.0170(4) Uani 1 1 d . . .
H1A H -0.0488 0.8590 -0.3207 0.020 Uiso 1 1 calc R . .
H1B H 0.0335 0.7120 -0.3502 0.020 Uiso 1 1 calc R . .
C2 C -0.2281(3) 0.8293(2) -0.47609(17) 0.0171(4) Uani 1 1 d . . .
C3 C -0.3787(3) 0.8434(2) -0.51824(18) 0.0215(5) Uani 1 1 d . . .
H3 H -0.3715 0.8686 -0.5952 0.026 Uiso 1 1 calc R . .
C4 C -0.5445(3) 0.8197(2) -0.44513(19) 0.0220(5) Uani 1 1 d . . .
H4 H -0.6510 0.8290 -0.4729 0.026 Uiso 1 1 calc R . .
C5 C -0.5550(3) 0.7834(2) -0.33431(19) 0.0204(4) Uani 1 1 d . . .
H5 H -0.6684 0.7686 -0.2852 0.024 Uiso 1 1 calc R . .
C6 C -0.3973(3) 0.7683(2) -0.29416(17) 0.0174(4) Uani 1 1 d . . .
C7 C -0.1135(3) 0.5353(2) -0.1241(2) 0.0262(5) Uani 1 1 d . . .
H7A H -0.1659 0.5161 -0.0444 0.039 Uiso 1 1 calc R . .
H7B H 0.0225 0.4973 -0.1422 0.039 Uiso 1 1 calc R . .
H7C H -0.1720 0.4983 -0.1661 0.039 Uiso 1 1 calc R . .
C8 C -0.2834(3) 0.8214(2) -0.04593(17) 0.0199(4) Uani 1 1 d . . .
H8A H -0.3437 0.9092 -0.0765 0.024 Uiso 1 1 calc R . .
H8B H -0.3816 0.7846 0.0089 0.024 Uiso 1 1 calc R . .
C9 C 0.0410(3) 0.7780(2) -0.04852(17) 0.0171(4) Uani 1 1 d . . .
C10 C 0.1901(3) 0.7822(2) -0.00665(19) 0.0222(5) Uani 1 1 d . . .
H10 H 0.3167 0.7478 -0.0444 0.027 Uiso 1 1 calc R . .
C11 C 0.1493(3) 0.8369(2) 0.08980(19) 0.0248(5) Uani 1 1 d . . .
H11 H 0.2489 0.8407 0.1188 0.030 Uiso 1 1 calc R . .
C12 C -0.0371(4) 0.8872(2) 0.14605(19) 0.0269(5) Uani 1 1 d . . .
H12 H -0.0643 0.9247 0.2130 0.032 Uiso 1 1 calc R . .
C13 C -0.1798(3) 0.8818(2) 0.10356(19) 0.0247(5) Uani 1 1 d . . .
H13 H -0.3069 0.9153 0.1410 0.030 Uiso 1 1 calc R . .
C14 C -0.4607(4) 0.3999(3) -0.2947(2) 0.0343(6) Uani 1 1 d . . .
N1 N -0.2353(2) 0.79027(16) -0.36623(14) 0.0149(3) Uani 1 1 d . . .
N2 N -0.1387(2) 0.82816(17) 0.00761(14) 0.0175(4) Uani 1 1 d . . .
O1 O -0.3911(2) 0.73334(15) -0.19138(12) 0.0204(3) Uani 1 1 d . . .
O2 O 0.0614(2) 0.72880(15) -0.13865(12) 0.0192(3) Uani 1 1 d . . .
Si1 Si -0.16127(8) 0.71392(6) -0.16169(5) 0.01689(14) Uani 1 1 d . . .
Cl1 Cl -0.02190(7) 0.86179(5) -0.55766(4) 0.02089(13) Uani 1 1 d . . .
Cl2 Cl -0.36419(7) 1.07634(5) -0.27311(4) 0.01959(13) Uani 1 1 d . . .
Cl3 Cl -0.54362(10) 0.44762(7) -0.15916(6) 0.03906(17) Uani 1 1 d . . .
Cl4 Cl -0.26223(10) 0.45858(7) -0.36804(6) 0.04118(18) Uani 1 1 d . . .
Cl5 Cl -0.35819(11) 0.54407(8) -0.63469(7) 0.04602(19) Uani 1 1 d . . .
H4A H -0.418(4) 0.307(3) -0.296(2) 0.038(8) Uiso 1 1 d . . .
 
 
_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 N1 1.477(2) . ?
C1 Si1 1.898(2) . ?
C2 C3 1.364(3) . ?
C2 N1 1.365(3) . ?
C2 Cl1 1.716(2) . ?
C3 C4 1.403(3) . ?
C4 C5 1.369(3) . ?
C5 C6 1.397(3) . ?
C6 O1 1.295(3) . ?
C6 N1 1.369(3) . ?
C7 Si1 1.860(2) . ?
C8 N2 1.479(3) . ?
C8 Si1 1.897(2) . ?
C9 O2 1.297(3) . ?
C9 N2 1.360(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.371(3) . ?
C11 C12 1.400(4) . ?
C12 C13 1.368(3) . ?
C13 N2 1.359(3) . ?
C14 Cl5 1.764(3) 2_464 ?
C14 Cl4 1.765(3) . ?
C14 Cl3 1.767(3) . ?
O1 Si1 1.8505(15) . ?
O2 Si1 1.8671(15) . ?
Cl5 C14 1.764(3) 2_464 ?
 
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 C1 Si1 107.44(13) . . ?
C3 C2 N1 121.41(19) . . ?
C3 C2 Cl1 121.84(17) . . ?
N1 C2 Cl1 116.74(15) . . ?
C2 C3 C4 118.3(2) . . ?
C5 C4 C3 120.9(2) . . ?
C4 C5 C6 119.3(2) . . ?
O1 C6 N1 116.08(18) . . ?
O1 C6 C5 124.47(19) . . ?
N1 C6 C5 119.46(19) . . ?
N2 C8 Si1 107.37(14) . . ?
O2 C9 N2 116.40(18) . . ?
O2 C9 C10 124.5(2) . . ?
N2 C9 C10 119.1(2) . . ?
C11 C10 C9 118.7(2) . . ?
C10 C11 C12 120.8(2) . . ?
C13 C12 C11 119.3(2) . . ?
N2 C13 C12 119.7(2) . . ?
Cl5 C14 Cl4 111.01(15) 2_464 . ?
Cl5 C14 Cl3 109.89(15) 2_464 . ?
Cl4 C14 Cl3 110.51(15) . . ?
C2 N1 C6 120.61(17) . . ?
C2 N1 C1 124.78(17) . . ?
C6 N1 C1 114.53(16) . . ?
C13 N2 C9 122.36(19) . . ?
C13 N2 C8 123.36(18) . . ?
C9 N2 C8 114.26(17) . . ?
C6 O1 Si1 115.61(13) . . ?
C9 O2 Si1 114.64(13) . . ?
O1 Si1 C7 95.80(9) . . ?
O1 Si1 O2 168.99(7) . . ?
C7 Si1 O2 95.21(9) . . ?
O1 Si1 C8 89.38(8) . . ?
C7 Si1 C8 117.99(11) . . ?
O2 Si1 C8 85.35(8) . . ?
O1 Si1 C1 86.06(8) . . ?
C7 Si1 C1 117.15(11) . . ?
O2 Si1 C1 89.02(8) . . ?
C8 Si1 C1 124.85(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.365
_refine_diff_density_min   -0.598
_refine_diff_density_rms    0.074
 
