 
data_97src026
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C14 H24 Br N O2 Si' 
_chemical_formula_weight          346.34 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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' 
 'Br'  'Br'  -0.2901   2.4595 
 '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                    6.0900(10) 
_cell_length_b                    8.114(2) 
_cell_length_c                    18.467(4) 
_cell_angle_alpha                 101.11(3) 
_cell_angle_beta                  95.30(3) 
_cell_angle_gamma                 106.29(3) 
_cell_volume                      849.0(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     3586 
_cell_measurement_theta_min       2.28 
_cell_measurement_theta_max       24.87 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.12 
_exptl_crystal_size_min            0.10
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.355 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              360 
_exptl_absorpt_coefficient_mu     2.490 
_exptl_absorpt_correction_type    refdelf
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR571 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Nonius FAST TV area detector' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3586 
_diffrn_reflns_av_R_equivalents   0.0442 
_diffrn_reflns_av_sigmaI/netI     0.1177 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        4 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          2.28 
_diffrn_reflns_theta_max          24.87 
_reflns_number_total              2347 
_reflns_number_observed           1666 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        
'MADNESS (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        
'MADNESS (Pflugrath & Messerschmidt, 1989)'
_computing_data_reduction         
'MADNESS (Pflugrath & Messerschmidt, 1989)'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-92 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F² for ALL reflections except for 0 with very negative F² 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F², conventional R-factors R 
 are based on F, with F set to zero for negative F². The observed criterion 
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0129P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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          2347 
_refine_ls_number_parameters      178 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0515 
_refine_ls_R_factor_obs           0.0343 
_refine_ls_wR_factor_all          0.0671 
_refine_ls_wR_factor_obs          0.0643 
_refine_ls_goodness_of_fit_all    0.730 
_refine_ls_goodness_of_fit_obs    0.843 
_refine_ls_restrained_S_all       0.730 
_refine_ls_restrained_S_obs       0.843 
_refine_ls_shift/esd_max          -0.007 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Br1 Br 0.28374(8) 0.68472(7) 0.00396(3) 0.0351(2) Uani 1 d . . 
Si1 Si -0.0910(2) 0.9959(2) -0.31844(7) 0.0283(3) Uani 1 d . . 
O1 O -0.1972(4) 0.5734(4) -0.1848(2) 0.0357(9) Uani 1 d . . 
H1 H -0.2999(16) 0.4979(48) -0.1732(20) 0.053 Uiso 1 calc R . 
O2 O 0.0650(4) 0.9250(4) -0.25922(15) 0.0243(7) Uani 1 d . . 
N1 N 0.3917(6) 1.3237(5) -0.1552(2) 0.0316(10) Uani 1 d . . 
C1 C 0.1352(6) 0.9050(6) -0.0783(2) 0.0237(11) Uani 1 d . . 
H1A H 0.2194(6) 0.9945(6) -0.0334(2) 0.028 Uiso 1 calc R . 
C2 C 0.0445(6) 0.7200(6) -0.0659(2) 0.0259(11) Uani 1 d . . 
H2 H -0.1028(6) 0.7023(6) -0.0465(2) 0.031 Uiso 1 calc R . 
C3 C 0.0171(6) 0.5966(6) -0.1403(2) 0.0278(12) Uani 1 d . . 
H3 H 0.0328(6) 0.4829(6) -0.1342(2) 0.033 Uiso 1 calc R . 
C4 C 0.2127(6) 0.6917(6) -0.1786(2) 0.0266(12) Uani 1 d . . 
H4A H 0.3459(6) 0.6501(6) -0.1712(2) 0.032 Uiso 1 calc R . 
H4B H 0.1610(6) 0.6696(6) -0.2318(2) 0.032 Uiso 1 calc R . 
C5 C 0.2763(6) 0.8886(5) -0.1429(2) 0.0195(10) Uani 1 d . . 
H5 H 0.4430(6) 0.9481(5) -0.1285(2) 0.023 Uiso 1 calc R . 
C6 C 0.1419(6) 0.9934(6) -0.1827(2) 0.0208(10) Uani 1 d . . 
C7 C -0.0364(6) 0.9641(6) -0.1283(2) 0.0239(11) Uani 1 d . . 
H7A H -0.1800(6) 0.8716(6) -0.1501(2) 0.029 Uiso 1 calc R . 
H7B H -0.0660(6) 1.0712(6) -0.1041(2) 0.029 Uiso 1 calc R . 
C8 C 0.2819(7) 1.1805(6) -0.1681(2) 0.0213(11) Uani 1 d . . 
C9 C -0.2867(7) 1.0983(7) -0.2691(3) 0.0457(14) Uani 1 d . . 
H9A H -0.3555(40) 1.1565(33) -0.3012(7) 0.069 Uiso 1 calc R . 
H9B H -0.2003(12) 1.1828(28) -0.2247(9) 0.069 Uiso 1 calc R . 
H9C H -0.4063(30) 1.0088(8) -0.2559(14) 0.069 Uiso 1 calc R . 
C10 C 0.1103(7) 1.1634(7) -0.3570(3) 0.049(2) Uani 1 d . . 
H10A H 0.0232(8) 1.2019(31) -0.3927(13) 0.073 Uiso 1 calc R . 
H10B H 0.2167(34) 1.1124(12) -0.3810(14) 0.073 Uiso 1 calc R . 
H10C H 0.1948(37) 1.2624(17) -0.3172(4) 0.073 Uiso 1 calc R . 
C11 C -0.2522(7) 0.7943(7) -0.3916(3) 0.0354(13) Uani 1 d . . 
C12 C -0.4185(7) 0.6626(7) -0.3563(3) 0.055(2) Uani 1 d . . 
H12A H -0.3329(11) 0.6383(33) -0.3155(12) 0.082 Uiso 1 calc R . 
H12B H -0.4922(40) 0.5551(15) -0.3932(6) 0.082 Uiso 1 calc R . 
H12C H -0.5341(33) 0.7125(17) -0.3382(15) 0.082 Uiso 1 calc R . 
C13 C -0.3907(7) 0.8450(7) -0.4527(3) 0.051(2) Uani 1 d . . 
H13A H -0.2862(8) 0.9239(35) -0.4757(13) 0.077 Uiso 1 calc R . 
H13B H -0.4951(42) 0.9022(40) -0.4309(4) 0.077 Uiso 1 calc R . 
H13C H -0.4775(44) 0.7407(9) -0.4897(10) 0.077 Uiso 1 calc R . 
C14 C -0.0815(8) 0.7050(8) -0.4277(3) 0.064(2) Uani 1 d . . 
H14A H 0.0316(38) 0.7896(14) -0.4457(18) 0.095 Uiso 1 calc R . 
H14B H -0.1656(11) 0.6085(31) -0.4686(14) 0.095 Uiso 1 calc R . 
H14C H -0.0050(47) 0.6618(43) -0.3911(7) 0.095 Uiso 1 calc R . 
 
 
_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 
Br1 C2 1.974(4) . ? 
Si1 O2 1.669(3) . ? 
Si1 C9 1.845(4) . ? 
Si1 C10 1.859(5) . ? 
Si1 C11 1.862(5) . ? 
O1 C3 1.420(4) . ? 
O2 C6 1.397(5) . ? 
N1 C8 1.132(5) . ? 
C1 C2 1.517(5) . ? 
C1 C5 1.539(6) . ? 
C1 C7 1.565(5) . ? 
C2 C3 1.501(6) . ? 
C3 C4 1.537(5) . ? 
C4 C5 1.528(6) . ? 
C5 C6 1.567(5) . ? 
C6 C8 1.475(6) . ? 
C6 C7 1.547(5) . ? 
C11 C13 1.534(6) . ? 
C11 C12 1.541(6) . ? 
C11 C14 1.554(6) . ? 
 
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 Si1 C9 110.2(2) . . ? 
O2 Si1 C10 108.5(2) . . ? 
C9 Si1 C10 109.0(2) . . ? 
O2 Si1 C11 104.5(2) . . ? 
C9 Si1 C11 112.2(2) . . ? 
C10 Si1 C11 112.3(2) . . ? 
C6 O2 Si1 129.0(3) . . ? 
C2 C1 C5 105.5(3) . . ? 
C2 C1 C7 115.8(3) . . ? 
C5 C1 C7 89.3(3) . . ? 
C3 C2 C1 106.2(4) . . ? 
C3 C2 Br1 108.8(3) . . ? 
C1 C2 Br1 107.7(3) . . ? 
O1 C3 C2 111.2(3) . . ? 
O1 C3 C4 108.0(3) . . ? 
C2 C3 C4 104.5(4) . . ? 
C5 C4 C3 106.9(4) . . ? 
C4 C5 C1 106.3(3) . . ? 
C4 C5 C6 115.4(3) . . ? 
C1 C5 C6 89.3(3) . . ? 
O2 C6 C8 110.7(3) . . ? 
O2 C6 C7 118.6(3) . . ? 
C8 C6 C7 111.3(4) . . ? 
O2 C6 C5 115.7(4) . . ? 
C8 C6 C5 109.9(3) . . ? 
C7 C6 C5 89.0(3) . . ? 
C6 C7 C1 89.1(3) . . ? 
N1 C8 C6 178.4(4) . . ? 
C13 C11 C12 109.7(3) . . ? 
C13 C11 C14 108.6(4) . . ? 
C12 C11 C14 109.0(4) . . ? 
C13 C11 Si1 109.4(3) . . ? 
C12 C11 Si1 109.6(3) . . ? 
C14 C11 Si1 110.5(3) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
 C9 Si1 O2 C6 -30.8(4) . . . . ? 
 C10 Si1 O2 C6 88.5(4) . . . . ? 
 C11 Si1 O2 C6 -151.5(3) . . . . ? 
 C5 C1 C2 C3 -29.5(4) . . . . ? 
 C7 C1 C2 C3 67.4(4) . . . . ? 
 C5 C1 C2 Br1 87.0(3) . . . . ? 
 C7 C1 C2 Br1 -176.1(3) . . . . ? 
 C1 C2 C3 O1 -83.3(4) . . . . ? 
 Br1 C2 C3 O1 161.0(3) . . . . ? 
 C1 C2 C3 C4 32.9(4) . . . . ? 
 Br1 C2 C3 C4 -82.8(3) . . . . ? 
 O1 C3 C4 C5 94.7(4) . . . . ? 
 C2 C3 C4 C5 -23.8(4) . . . . ? 
 C3 C4 C5 C1 5.9(4) . . . . ? 
 C3 C4 C5 C6 -91.3(4) . . . . ? 
 C2 C1 C5 C4 14.1(4) . . . . ? 
 C7 C1 C5 C4 -102.5(3) . . . . ? 
 C2 C1 C5 C6 130.4(3) . . . . ? 
 C7 C1 C5 C6 13.8(3) . . . . ? 
 Si1 O2 C6 C8 -56.9(4) . . . . ? 
 Si1 O2 C6 C7 73.4(5) . . . . ? 
 Si1 O2 C6 C5 177.3(2) . . . . ? 
 C4 C5 C6 O2 -27.6(5) . . . . ? 
 C1 C5 C6 O2 -135.4(3) . . . . ? 
 C4 C5 C6 C8 -153.8(4) . . . . ? 
 C1 C5 C6 C8 98.4(4) . . . . ? 
 C4 C5 C6 C7 93.9(4) . . . . ? 
 C1 C5 C6 C7 -13.9(3) . . . . ? 
 O2 C6 C7 C1 132.6(4) . . . . ? 
 C8 C6 C7 C1 -97.3(3) . . . . ? 
 C5 C6 C7 C1 13.7(3) . . . . ? 
 C2 C1 C7 C6 -120.9(4) . . . . ? 
 C5 C1 C7 C6 -13.9(3) . . . . ? 
 O2 C6 C8 N1 -158.5(167) . . . . ? 
 C7 C6 C8 N1 67.5(169) . . . . ? 
 C5 C6 C8 N1 -29.5(170) . . . . ? 
 O2 Si1 C11 C13 -176.1(3) . . . . ? 
 C9 Si1 C11 C13 64.5(4) . . . . ? 
 C10 Si1 C11 C13 -58.7(4) . . . . ? 
 O2 Si1 C11 C12 63.5(3) . . . . ? 
 C9 Si1 C11 C12 -55.8(4) . . . . ? 
 C10 Si1 C11 C12 -179.0(3) . . . . ? 
 O2 Si1 C11 C14 -56.6(4) . . . . ? 
 C9 Si1 C11 C14 -176.0(3) . . . . ? 
 C10 Si1 C11 C14 60.9(4) . . . . ? 
 
_refine_diff_density_max    0.491 
_refine_diff_density_min   -0.323 
_refine_diff_density_rms    0.067 
