data_04src0845
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. I. R. Butler
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H20 Br N O2 Si'
_chemical_formula_sum
 'C20 H20 Br N O2 Si'
_chemical_formula_weight          414.37
 
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
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.7406(14)
_cell_length_b                    11.7940(19)
_cell_length_c                    11.945(3)
_cell_angle_alpha                 87.687(17)
_cell_angle_beta                  86.67(2)
_cell_angle_gamma                 81.403(18)
_cell_volume                      936.9(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4247
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             Yellow
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.469
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              424
_exptl_absorpt_coefficient_mu     2.271
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6595
_exptl_absorpt_correction_T_max   0.9560
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_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    '10cm confocal mirrors'
_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             21063
_diffrn_reflns_av_R_equivalents   0.0632
_diffrn_reflns_av_sigmaI/netI     0.0549
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4306
_reflns_number_gt                 3511
_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     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_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)+(0.0149P)²+0.9398P] 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          4306
_refine_ls_number_parameters      231
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0584
_refine_ls_R_factor_gt            0.0402
_refine_ls_wR_factor_ref          0.0774
_refine_ls_wR_factor_gt           0.0718
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_refine_ls_shift/su_max           0.001
_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 0.3326(4) 0.7621(2) 0.5683(2) 0.0215(5) Uani 1 1 d . . .
C2 C 0.5147(4) 0.6938(2) 0.5446(2) 0.0241(6) Uani 1 1 d . . .
H2 H 0.6058 0.7197 0.4891 0.029 Uiso 1 1 calc R . .
C3 C 0.5670(4) 0.5906(2) 0.5985(2) 0.0241(6) Uani 1 1 d . . .
C4 C 0.4307(4) 0.5526(2) 0.6809(2) 0.0229(6) Uani 1 1 d . . .
C5 C 0.2437(4) 0.6226(2) 0.7071(2) 0.0192(5) Uani 1 1 d . . .
C6 C 0.1049(4) 0.5843(2) 0.7947(2) 0.0221(6) Uani 1 1 d . . .
C7 C -0.0939(4) 0.6544(2) 0.8165(2) 0.0209(5) Uani 1 1 d . . .
C8 C -0.2307(4) 0.6131(2) 0.8950(2) 0.0252(6) Uani 1 1 d . . .
H8 H -0.1933 0.5425 0.9348 0.030 Uiso 1 1 calc R . .
C9 C -0.4187(4) 0.6742(2) 0.9145(2) 0.0292(6) Uani 1 1 d . . .
H9 H -0.5110 0.6457 0.9676 0.035 Uiso 1 1 calc R . .
C10 C -0.4739(4) 0.7776(2) 0.8568(2) 0.0271(6) Uani 1 1 d . . .
H10 H -0.6042 0.8196 0.8701 0.033 Uiso 1 1 calc R . .
C11 C -0.3387(4) 0.8195(2) 0.7797(2) 0.0247(6) Uani 1 1 d . . .
H11 H -0.3763 0.8904 0.7406 0.030 Uiso 1 1 calc R . .
C12 C -0.1481(4) 0.7577(2) 0.7597(2) 0.0194(5) Uani 1 1 d . . .
C13 C -0.0042(4) 0.8078(2) 0.6754(2) 0.0183(5) Uani 1 1 d . . .
C14 C 0.1941(3) 0.7292(2) 0.6485(2) 0.0175(5) Uani 1 1 d . . .
C15 C 0.7683(4) 0.5207(2) 0.5721(3) 0.0321(7) Uani 1 1 d . . .
H15A H 0.8441 0.5623 0.5159 0.048 Uiso 1 1 calc R . .
H15B H 0.7493 0.4469 0.5425 0.048 Uiso 1 1 calc R . .
H15C H 0.8429 0.5072 0.6405 0.048 Uiso 1 1 calc R . .
C16 C 0.0398(4) 0.9156(2) 0.7216(2) 0.0194(5) Uani 1 1 d . . .
C17 C 0.0700(4) 1.0025(2) 0.7623(2) 0.0229(6) Uani 1 1 d . . .
C18 C 0.0183(6) 1.2541(3) 0.7131(3) 0.0459(8) Uani 1 1 d . . .
H18A H 0.1000 1.2434 0.6427 0.069 Uiso 1 1 calc R . .
H18B H 0.0278 1.3295 0.7421 0.069 Uiso 1 1 calc R . .
H18C H -0.1221 1.2492 0.6995 0.069 Uiso 1 1 calc R . .
C19 C 0.3835(5) 1.1369(3) 0.8344(3) 0.0448(8) Uani 1 1 d . . .
H19A H 0.4302 1.0749 0.8879 0.067 Uiso 1 1 calc R . .
H19B H 0.4072 1.2104 0.8626 0.067 Uiso 1 1 calc R . .
H19C H 0.4570 1.1235 0.7618 0.067 Uiso 1 1 calc R . .
C20 C -0.0359(5) 1.1654(3) 0.9519(3) 0.0443(8) Uani 1 1 d . . .
H20A H -0.1754 1.1546 0.9426 0.066 Uiso 1 1 calc R . .
H20B H -0.0327 1.2438 0.9750 0.066 Uiso 1 1 calc R . .
H20C H 0.0222 1.1107 1.0094 0.066 Uiso 1 1 calc R . .
N1 N 0.4823(3) 0.44869(19) 0.7329(2) 0.0312(5) Uani 1 1 d . . .
H1A H 0.5983 0.4068 0.7151 0.037 Uiso 1 1 calc R . .
H1B H 0.3997 0.4233 0.7845 0.037 Uiso 1 1 calc R . .
O1 O 0.1470(3) 0.49400(16) 0.85013(16) 0.0328(5) Uani 1 1 d . . .
O2 O -0.1166(2) 0.83103(15) 0.57585(14) 0.0214(4) Uani 1 1 d . . .
H2A H -0.0504 0.8655 0.5273 0.032 Uiso 1 1 calc R . .
Si1 Si 0.11139(11) 1.14076(6) 0.81711(6) 0.02318(17) Uani 1 1 d . . .
Br1 Br 0.29438(4) 0.90474(2) 0.48520(2) 0.02714(9) Uani 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 C14 1.384(3) . ?
C1 C2 1.385(4) . ?
C1 Br1 1.910(3) . ?
C2 C3 1.362(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.413(4) . ?
C3 C15 1.503(4) . ?
C4 N1 1.359(3) . ?
C4 C5 1.426(3) . ?
C5 C14 1.418(3) . ?
C5 C6 1.465(4) . ?
C6 O1 1.236(3) . ?
C6 C7 1.481(4) . ?
C7 C12 1.381(3) . ?
C7 C8 1.401(4) . ?
C8 C9 1.373(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.521(3) . ?
C13 O2 1.442(3) . ?
C13 C16 1.482(3) . ?
C13 C14 1.534(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.201(4) . ?
C17 Si1 1.847(3) . ?
C18 Si1 1.851(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 Si1 1.851(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 Si1 1.851(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
O2 H2A 0.8400 . ?
 
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
C14 C1 C2 121.7(2) . . ?
C14 C1 Br1 123.64(19) . . ?
C2 C1 Br1 114.66(19) . . ?
C3 C2 C1 122.0(2) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 C15 120.1(2) . . ?
C4 C3 C15 121.2(2) . . ?
N1 C4 C3 118.4(2) . . ?
N1 C4 C5 121.6(2) . . ?
C3 C4 C5 120.0(2) . . ?
C14 C5 C4 119.6(2) . . ?
C14 C5 C6 120.5(2) . . ?
C4 C5 C6 119.8(2) . . ?
O1 C6 C5 122.1(2) . . ?
O1 C6 C7 118.6(2) . . ?
C5 C6 C7 119.3(2) . . ?
C12 C7 C8 119.7(2) . . ?
C12 C7 C6 121.5(2) . . ?
C8 C7 C6 118.9(2) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.9(2) . . ?
C7 C12 C13 121.9(2) . . ?
C11 C12 C13 118.2(2) . . ?
O2 C13 C16 110.96(19) . . ?
O2 C13 C12 104.12(19) . . ?
C16 C13 C12 107.3(2) . . ?
O2 C13 C14 110.16(19) . . ?
C16 C13 C14 109.2(2) . . ?
C12 C13 C14 115.1(2) . . ?
C1 C14 C5 118.1(2) . . ?
C1 C14 C13 120.6(2) . . ?
C5 C14 C13 121.3(2) . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 177.5(3) . . ?
C16 C17 Si1 176.6(2) . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C13 O2 H2A 109.5 . . ?
C17 Si1 C19 108.85(13) . . ?
C17 Si1 C20 109.16(14) . . ?
C19 Si1 C20 111.51(16) . . ?
C17 Si1 C18 107.06(13) . . ?
C19 Si1 C18 110.91(17) . . ?
C20 Si1 C18 109.23(16) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.561
_refine_diff_density_min   -0.486
_refine_diff_density_rms    0.080
