 
data_06182016_0m
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H20 F N O3 Si' 
_chemical_formula_weight          357.45

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'
 'F'  'F'   0.0171   0.0103
 '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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.84(3)
_cell_length_b                    7.717(19)
_cell_length_c                    18.32(4)
_cell_angle_alpha                 81.71(9)
_cell_angle_beta                  85.48(10)
_cell_angle_gamma                 72.46(7)
_cell_volume                      911(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     111(2)
_cell_measurement_reflns_used     975
_cell_measurement_theta_min       2.5
_cell_measurement_theta_max       24.2
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.303          
_exptl_crystal_F_000              376
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.100
_exptl_crystal_size_min           0.100
_exptl_absorpt_coefficient_mu     0.156
_shelx_estimated_absorpt_T_min    0.970
_shelx_estimated_absorpt_T_max    0.985
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.5032  
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    'sadabs'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       111(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker Kappa Apex II'
_diffrn_measurement_method        'Omega Scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             4651
_diffrn_reflns_av_unetI/netI      0.0971
_diffrn_reflns_av_R_equivalents   0.0489
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          1.124
_diffrn_reflns_theta_max          24.706
_diffrn_reflns_theta_full         24.706
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3077
_reflns_number_gt                 2055
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1396P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3077
_refine_ls_number_parameters      229
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1109
_refine_ls_R_factor_gt            0.0745
_refine_ls_wR_factor_ref          0.2328
_refine_ls_wR_factor_gt           0.2064
_refine_ls_goodness_of_fit_ref    1.044
_refine_ls_restrained_S_all       1.044
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.7127(7) 0.2620(6) 0.3174(2) 0.0191(10) Uani 1 1 d . . . . .
H1 H 0.7706 0.1459 0.2947 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7205(7) 0.4291(6) 0.2577(2) 0.0192(10) Uani 1 1 d . . . . .
H2 H 0.8033 0.4997 0.2762 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4957(7) 0.5454(6) 0.2544(2) 0.0197(10) Uani 1 1 d . . . . .
C4 C 0.3870(7) 0.4539(6) 0.2994(2) 0.0202(10) Uani 1 1 d . . . . .
H4 H 0.2423 0.5010 0.3059 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8130(6) 0.3686(6) 0.1835(2) 0.0182(9) Uani 1 1 d . . . . .
C6 C 0.7029(7) 0.2955(6) 0.1405(2) 0.0239(10) Uani 1 1 d . . . . .
H6 H 0.5710 0.2867 0.1576 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7850(8) 0.2361(6) 0.0733(2) 0.0279(11) Uani 1 1 d . . . . .
H7 H 0.7118 0.1854 0.0444 0.033 Uiso 1 1 calc R U . . .
C8 C 0.9746(8) 0.2529(7) 0.0500(2) 0.0297(12) Uani 1 1 d . . . . .
C9 C 1.0882(8) 0.3247(7) 0.0895(2) 0.0312(12) Uani 1 1 d . . . . .
H9 H 1.2188 0.3349 0.0713 0.037 Uiso 1 1 calc R U . . .
C10 C 1.0040(7) 0.3823(6) 0.1574(2) 0.0248(11) Uani 1 1 d . . . . .
H10 H 1.0795 0.4315 0.1860 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4732(9) 0.7812(7) 0.1028(2) 0.0357(13) Uani 1 1 d . . . . .
H11A H 0.6233 0.7495 0.0985 0.054 Uiso 1 1 calc R U . . .
H11B H 0.4135 0.9038 0.0765 0.054 Uiso 1 1 calc R U . . .
H11C H 0.4273 0.6918 0.0812 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4848(7) 0.9419(6) 0.2444(3) 0.0296(11) Uani 1 1 d . . . . .
H12A H 0.4604 0.9264 0.2980 0.044 Uiso 1 1 calc R U . . .
H12B H 0.4127 1.0677 0.2241 0.044 Uiso 1 1 calc R U . . .
H12C H 0.6324 0.9175 0.2330 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1009(7) 0.8440(7) 0.2102(3) 0.0310(12) Uani 1 1 d . . . . .
H13A H 0.0528 0.7578 0.1873 0.047 Uiso 1 1 calc R U . . .
H13B H 0.0439 0.9681 0.1849 0.047 Uiso 1 1 calc R U . . .
H13C H 0.0556 0.8402 0.2624 0.047 Uiso 1 1 calc R U . . .
C14 C 0.8306(7) 0.2506(6) 0.3861(2) 0.0198(10) Uani 1 1 d . . . . .
C15 C 0.7313(7) 0.3147(6) 0.4505(2) 0.0250(11) Uani 1 1 d . . . . .
H15 H 0.5858 0.3608 0.4533 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8463(7) 0.3113(6) 0.5113(2) 0.0234(10) Uani 1 1 d . . . . .
H16 H 0.7798 0.3564 0.5552 0.028 Uiso 1 1 calc R U . . .
C17 C 1.0581(7) 0.2410(6) 0.5062(2) 0.0202(10) Uani 1 1 d . . . . .
C18 C 1.1626(7) 0.1710(6) 0.4437(2) 0.0229(10) Uani 1 1 d . . . . .
H18 H 1.3078 0.1209 0.4416 0.027 Uiso 1 1 calc R U . . .
C19 C 1.0435(7) 0.1777(6) 0.3835(2) 0.0241(11) Uani 1 1 d . . . . .
H19 H 1.1101 0.1311 0.3399 0.029 Uiso 1 1 calc R U . . .
F1 F 1.0564(5) 0.1940(4) -0.01634(15) 0.0451(9) Uani 1 1 d . . . . .
N1 N 1.1817(6) 0.2417(5) 0.56897(19) 0.0253(9) Uani 1 1 d . . . . .
O1 O 0.4958(5) 0.2868(4) 0.33636(16) 0.0229(7) Uani 1 1 d . . . . .
O2 O 1.0903(5) 0.3084(5) 0.62426(16) 0.0374(9) Uani 1 1 d . . . . .
O3 O 1.3696(5) 0.1815(5) 0.56388(18) 0.0385(10) Uani 1 1 d . . . . .
Si1 Si 0.38794(19) 0.77848(17) 0.20268(6) 0.0204(4) 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 O1 1.457(7) . ?
C1 C14 1.526(6) . ?
C1 C2 1.577(6) . ?
C1 H1 1.0000 . ?
C2 C3 1.530(8) . ?
C2 C5 1.529(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.335(7) . ?
C3 Si1 1.869(6) . ?
C4 O1 1.387(6) . ?
C4 H4 0.9500 . ?
C5 C10 1.384(8) . ?
C5 C6 1.407(7) . ?
C6 C7 1.394(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(8) . ?
C8 F1 1.377(6) . ?
C9 C10 1.404(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 Si1 1.875(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 Si1 1.864(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 Si1 1.873(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.391(7) . ?
C14 C19 1.393(8) . ?
C15 C16 1.406(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(7) . ?
C17 N1 1.481(6) . ?
C18 C19 1.407(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 O3 1.228(7) . ?
N1 O2 1.240(5) . ?
 
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
O1 C1 C14 110.6(4) . . ?
O1 C1 C2 105.7(3) . . ?
C14 C1 C2 113.3(4) . . ?
O1 C1 H1 109.0 . . ?
C14 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C3 C2 C5 113.4(4) . . ?
C3 C2 C1 102.9(4) . . ?
C5 C2 C1 112.3(4) . . ?
C3 C2 H2 109.3 . . ?
C5 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C4 C3 C2 107.1(4) . . ?
C4 C3 Si1 125.0(4) . . ?
C2 C3 Si1 127.8(3) . . ?
C3 C4 O1 116.7(4) . . ?
C3 C4 H4 121.6 . . ?
O1 C4 H4 121.6 . . ?
C10 C5 C6 118.8(4) . . ?
C10 C5 C2 121.6(4) . . ?
C6 C5 C2 119.6(4) . . ?
C7 C6 C5 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 118.0(4) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 123.6(5) . . ?
C7 C8 F1 118.2(4) . . ?
C9 C8 F1 118.2(5) . . ?
C8 C9 C10 117.6(5) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C5 C10 C9 121.1(4) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.4(4) . . ?
C15 C14 C1 121.6(4) . . ?
C19 C14 C1 118.9(4) . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 122.8(4) . . ?
C16 C17 N1 119.6(4) . . ?
C18 C17 N1 117.6(4) . . ?
C17 C18 C19 116.9(5) . . ?
C17 C18 H18 121.5 . . ?
C19 C18 H18 121.5 . . ?
C14 C19 C18 121.9(4) . . ?
C14 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
O3 N1 O2 122.5(4) . . ?
O3 N1 C17 119.4(4) . . ?
O2 N1 C17 118.1(4) . . ?
C4 O1 C1 107.3(3) . . ?
C12 Si1 C3 107.9(3) . . ?
C12 Si1 C13 110.7(3) . . ?
C3 Si1 C13 109.2(2) . . ?
C12 Si1 C11 109.2(3) . . ?
C3 Si1 C11 110.7(2) . . ?
C13 Si1 C11 109.2(3) . . ?
 
_refine_diff_density_max    1.027
_refine_diff_density_min   -0.681
_refine_diff_density_rms    0.108



