# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SR116F1-16
_database_code_depnum_ccdc_archive 'CCDC 1483007'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
3-(4-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)-5-(trimethylsilyl)isoxazole

_chemical_formula_moiety         'C19 H20 F N O3 S Si'
_chemical_formula_sum            'C19 H20 F N O3 S Si'
_chemical_formula_weight         389.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0838 0.0720 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1265 0.1256 '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                   7.6192(5)
_cell_length_b                   10.3601(7)
_cell_length_c                   13.1271(9)
_cell_angle_alpha                102.578(4)
_cell_angle_beta                 92.847(4)
_cell_angle_gamma                101.855(4)
_cell_volume                     984.9(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2343
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      21.78
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   0.6776
_exptl_transmission_factor_max   0.7464
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            30982
_diffrn_reflns_av_unetI/netI     0.1359
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.298
_diffrn_reflns_theta_max         32.811
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7110
_reflns_number_gt                3253
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²] 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     SHELXL
_refine_ls_extinction_coef       0.0069(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7110
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_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_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
O1 O 0.2692(2) -0.12899(15) 0.64698(12) 0.0323(4) Uani 1 1 d . . . . .
N1 N 0.3064(2) -0.03797(19) 0.58182(15) 0.0309(4) Uani 1 1 d . . . . .
C1 C 0.2084(3) 0.0525(2) 0.61123(17) 0.0264(5) Uani 1 1 d . . . . .
C2 C 0.1025(3) 0.0219(2) 0.69358(17) 0.0252(5) Uani 1 1 d . . . . .
C3 C 0.1457(3) -0.0921(2) 0.71396(18) 0.0300(5) Uani 1 1 d . . . . .
C4 C 0.2210(3) 0.1659(2) 0.55863(17) 0.0262(5) Uani 1 1 d . . . . .
C5 C 0.3790(3) 0.2106(2) 0.51410(18) 0.0313(5) Uani 1 1 d . . . . .
H5 H 0.4788 0.1699 0.5201 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3902(3) 0.3139(2) 0.46125(19) 0.0350(6) Uani 1 1 d . . . . .
H6 H 0.4960 0.3434 0.4297 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2451(3) 0.3726(2) 0.45550(19) 0.0349(6) Uani 1 1 d . . . . .
C8 C 0.0893(3) 0.3328(2) 0.49900(19) 0.0347(6) Uani 1 1 d . . . . .
H8 H -0.0087 0.3754 0.4935 0.042 Uiso 1 1 calc R U . . .
C9 C 0.0776(3) 0.2293(2) 0.55100(18) 0.0293(5) Uani 1 1 d . . . . .
H9 H -0.0294 0.2009 0.5819 0.035 Uiso 1 1 calc R U . . .
F1 F 0.2561(2) 0.47434(14) 0.40381(12) 0.0495(4) Uani 1 1 d . . . . .
C10 C -0.0204(3) 0.1016(2) 0.74839(17) 0.0248(5) Uani 1 1 d . . . . .
C11 C -0.2065(3) 0.0590(2) 0.72631(18) 0.0292(5) Uani 1 1 d . . . . .
H11 H -0.2569 -0.0243 0.6774 0.035 Uiso 1 1 calc R U . . .
C12 C -0.3187(3) 0.1373(2) 0.77532(17) 0.0296(5) Uani 1 1 d . . . . .
H12 H -0.4457 0.1074 0.7609 0.036 Uiso 1 1 calc R U . . .
C13 C -0.2450(3) 0.2589(2) 0.84514(16) 0.0236(5) Uani 1 1 d . . . . .
C14 C -0.0604(3) 0.3033(2) 0.86868(17) 0.0264(5) Uani 1 1 d . . . . .
H14 H -0.0107 0.3873 0.9170 0.032 Uiso 1 1 calc R U . . .
C15 C 0.0511(3) 0.2228(2) 0.82041(17) 0.0275(5) Uani 1 1 d . . . . .
H15 H 0.1780 0.2513 0.8370 0.033 Uiso 1 1 calc R U . . .
S1 S -0.38808(7) 0.35795(6) 0.90914(4) 0.02589(15) Uani 1 1 d . . . . .
O2 O -0.54193(19) 0.26782(16) 0.93248(13) 0.0352(4) Uani 1 1 d . . . . .
O3 O -0.2821(2) 0.45997(16) 0.99407(13) 0.0379(4) Uani 1 1 d . . . . .
C16 C -0.4589(3) 0.4376(3) 0.8141(2) 0.0387(6) Uani 1 1 d . . . . .
H16A H -0.5410 0.4942 0.8435 0.058 Uiso 1 1 calc R U . . .
H16B H -0.5214 0.3686 0.7526 0.058 Uiso 1 1 calc R U . . .
H16C H -0.3538 0.4944 0.7934 0.058 Uiso 1 1 calc R U . . .
Si1 Si 0.10448(10) -0.18762(7) 0.82088(5) 0.0383(2) Uani 1 1 d . . . . .
C17 C 0.2594(5) -0.0837(3) 0.9343(2) 0.0786(11) Uani 1 1 d . . . . .
H17A H 0.3832 -0.0903 0.9216 0.118 Uiso 1 1 calc R U . . .
H17B H 0.2278 -0.1164 0.9971 0.118 Uiso 1 1 calc R U . . .
H17C H 0.2498 0.0111 0.9448 0.118 Uiso 1 1 calc R U . . .
C18 C -0.1347(4) -0.2048(3) 0.8480(2) 0.0607(9) Uani 1 1 d . . . . .
H18A H -0.1583 -0.1146 0.8747 0.091 Uiso 1 1 calc R U . . .
H18B H -0.1593 -0.2589 0.9004 0.091 Uiso 1 1 calc R U . . .
H18C H -0.2129 -0.2500 0.7831 0.091 Uiso 1 1 calc R U . . .
C19 C 0.1579(4) -0.3553(3) 0.7739(2) 0.0537(8) Uani 1 1 d . . . . .
H19A H 0.1457 -0.4049 0.8296 0.081 Uiso 1 1 calc R U . . .
H19B H 0.2818 -0.3431 0.7545 0.081 Uiso 1 1 calc R U . . .
H19C H 0.0745 -0.4068 0.7125 0.081 Uiso 1 1 calc R U . . .


_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
O1 C3 1.374(2) .
O1 N1 1.402(2) .
N1 C1 1.321(3) .
C1 C2 1.432(3) .
C1 C4 1.476(3) .
C2 C3 1.365(3) .
C2 C10 1.484(3) .
C3 Si1 1.889(2) .
C4 C9 1.395(3) .
C4 C5 1.401(3) .
C5 C6 1.388(3) .
C5 H5 0.9500 .
C6 C7 1.373(3) .
C6 H6 0.9500 .
C7 F1 1.363(3) .
C7 C8 1.369(3) .
C8 C9 1.382(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C15 1.385(3) .
C10 C11 1.392(3) .
C11 C12 1.384(3) .
C11 H11 0.9500 .
C12 C13 1.377(3) .
C12 H12 0.9500 .
C13 C14 1.384(3) .
C13 S1 1.767(2) .
C14 C15 1.390(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
S1 O2 1.4319(15) .
S1 O3 1.4349(17) .
S1 C16 1.758(2) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
Si1 C17 1.837(3) .
Si1 C19 1.847(3) .
Si1 C18 1.854(3) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .

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
C3 O1 N1 110.04(15) . .
C1 N1 O1 105.34(16) . .
N1 C1 C2 111.43(19) . .
N1 C1 C4 118.82(19) . .
C2 C1 C4 129.76(18) . .
C3 C2 C1 105.22(18) . .
C3 C2 C10 127.62(19) . .
C1 C2 C10 127.09(19) . .
C2 C3 O1 107.96(19) . .
C2 C3 Si1 135.26(17) . .
O1 C3 Si1 115.96(15) . .
C9 C4 C5 118.9(2) . .
C9 C4 C1 121.41(19) . .
C5 C4 C1 119.72(19) . .
C6 C5 C4 120.3(2) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C7 C6 C5 118.6(2) . .
C7 C6 H6 120.7 . .
C5 C6 H6 120.7 . .
F1 C7 C8 118.6(2) . .
F1 C7 C6 118.7(2) . .
C8 C7 C6 122.7(2) . .
C7 C8 C9 118.7(2) . .
C7 C8 H8 120.7 . .
C9 C8 H8 120.7 . .
C8 C9 C4 120.8(2) . .
C8 C9 H9 119.6 . .
C4 C9 H9 119.6 . .
C15 C10 C11 119.23(19) . .
C15 C10 C2 119.57(19) . .
C11 C10 C2 121.2(2) . .
C12 C11 C10 120.3(2) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C13 C12 C11 119.64(19) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 121.16(19) . .
C12 C13 S1 119.68(15) . .
C14 C13 S1 119.13(17) . .
C13 C14 C15 118.8(2) . .
C13 C14 H14 120.6 . .
C15 C14 H14 120.6 . .
C10 C15 C14 120.83(19) . .
C10 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
O2 S1 O3 118.30(10) . .
O2 S1 C16 108.48(11) . .
O3 S1 C16 108.66(12) . .
O2 S1 C13 108.03(10) . .
O3 S1 C13 108.18(9) . .
C16 S1 C13 104.32(11) . .
S1 C16 H16A 109.5 . .
S1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
S1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C17 Si1 C19 111.86(15) . .
C17 Si1 C18 112.04(16) . .
C19 Si1 C18 111.22(14) . .
C17 Si1 C3 104.97(13) . .
C19 Si1 C3 107.61(12) . .
C18 Si1 C3 108.80(11) . .
Si1 C17 H17A 109.5 . .
Si1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
Si1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
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 . .

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
C3 O1 N1 C1 1.0(2) . . . .
O1 N1 C1 C2 -1.4(2) . . . .
O1 N1 C1 C4 178.50(18) . . . .
N1 C1 C2 C3 1.3(3) . . . .
C4 C1 C2 C3 -178.6(2) . . . .
N1 C1 C2 C10 178.4(2) . . . .
C4 C1 C2 C10 -1.4(4) . . . .
C1 C2 C3 O1 -0.6(2) . . . .
C10 C2 C3 O1 -177.7(2) . . . .
C1 C2 C3 Si1 168.1(2) . . . .
C10 C2 C3 Si1 -9.0(4) . . . .
N1 O1 C3 C2 -0.2(2) . . . .
N1 O1 C3 Si1 -171.38(14) . . . .
N1 C1 C4 C9 152.6(2) . . . .
C2 C1 C4 C9 -27.6(4) . . . .
N1 C1 C4 C5 -26.6(3) . . . .
C2 C1 C4 C5 153.2(2) . . . .
C9 C4 C5 C6 -1.5(3) . . . .
C1 C4 C5 C6 177.7(2) . . . .
C4 C5 C6 C7 1.3(3) . . . .
C5 C6 C7 F1 179.9(2) . . . .
C5 C6 C7 C8 -0.5(4) . . . .
F1 C7 C8 C9 179.7(2) . . . .
C6 C7 C8 C9 0.1(4) . . . .
C7 C8 C9 C4 -0.4(3) . . . .
C5 C4 C9 C8 1.1(3) . . . .
C1 C4 C9 C8 -178.2(2) . . . .
C3 C2 C10 C15 102.7(3) . . . .
C1 C2 C10 C15 -73.8(3) . . . .
C3 C2 C10 C11 -79.4(3) . . . .
C1 C2 C10 C11 104.1(3) . . . .
C15 C10 C11 C12 0.4(3) . . . .
C2 C10 C11 C12 -177.5(2) . . . .
C10 C11 C12 C13 0.9(3) . . . .
C11 C12 C13 C14 -1.1(3) . . . .
C11 C12 C13 S1 -179.13(17) . . . .
C12 C13 C14 C15 0.0(3) . . . .
S1 C13 C14 C15 178.05(16) . . . .
C11 C10 C15 C14 -1.5(3) . . . .
C2 C10 C15 C14 176.4(2) . . . .
C13 C14 C15 C10 1.3(3) . . . .
C12 C13 S1 O2 37.2(2) . . . .
C14 C13 S1 O2 -140.83(18) . . . .
C12 C13 S1 O3 166.39(17) . . . .
C14 C13 S1 O3 -11.7(2) . . . .
C12 C13 S1 C16 -78.1(2) . . . .
C14 C13 S1 C16 103.89(19) . . . .
C2 C3 Si1 C17 -74.7(3) . . . .
O1 C3 Si1 C17 93.4(2) . . . .
C2 C3 Si1 C19 166.0(2) . . . .
O1 C3 Si1 C19 -25.9(2) . . . .
C2 C3 Si1 C18 45.4(3) . . . .
O1 C3 Si1 C18 -146.53(18) . . . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O3 0.95 2.52 3.324(3) 142.9 2_567
C16 H16A O3 0.98 2.59 3.399(3) 140.1 2_467

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-1

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SR105F1-16
_database_code_depnum_ccdc_archive 'CCDC 1483008'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
4-(3-(4-fluorophenyl)-5-(trimethylsilyl)isoxazol-4-yl)benzenesulfonamide
;

_chemical_formula_moiety         'C18 H19 F N2 O3 S Si'
_chemical_formula_sum            'C18 H19 F N2 O3 S Si'
_chemical_formula_weight         390.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0838 0.0720 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1265 0.1256 '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                   9.705(6)
_cell_length_b                   9.854(6)
_cell_length_c                   11.726(8)
_cell_angle_alpha                65.43(3)
_cell_angle_beta                 68.51(3)
_cell_angle_gamma                76.92(2)
_cell_volume                     945(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9263
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      39.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   0.6448
_exptl_transmission_factor_max   0.7477
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.261
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            72195
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         39.539
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             11324
_reflns_number_gt                8349
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.5381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11324
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_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
N1 N 0.20703(11) 0.75459(10) 0.36915(9) 0.01754(16) Uani 1 1 d . . . . .
O1 O 0.20194(10) 0.81515(9) 0.45967(8) 0.01760(14) Uani 1 1 d . . . . .
C1 C 0.22246(11) 0.60811(11) 0.42866(9) 0.01432(15) Uani 1 1 d . . . . .
C2 C 0.22489(10) 0.56807(11) 0.56012(9) 0.01271(14) Uani 1 1 d . . . . .
C3 C 0.21271(11) 0.70164(11) 0.57448(9) 0.01448(16) Uani 1 1 d . . . . .
C4 C 0.23291(12) 0.51223(12) 0.35697(10) 0.01659(17) Uani 1 1 d . . . . .
C5 C 0.30618(14) 0.56046(14) 0.22089(11) 0.0220(2) Uani 1 1 d . . . . .
H5 H 0.3544 0.6505 0.1776 0.026 Uiso 1 1 calc R U . . .
C6 C 0.30864(15) 0.47738(17) 0.14933(14) 0.0287(3) Uani 1 1 d . . . . .
H6 H 0.3569 0.5102 0.0570 0.034 Uiso 1 1 calc R U . . .
C7 C 0.23993(15) 0.34685(17) 0.21483(16) 0.0294(3) Uani 1 1 d . . . . .
C8 C 0.16988(14) 0.29367(15) 0.34920(15) 0.0270(2) Uani 1 1 d . . . . .
H8 H 0.1250 0.2018 0.3918 0.032 Uiso 1 1 calc R U . . .
C9 C 0.16644(13) 0.37749(13) 0.42077(12) 0.02084(19) Uani 1 1 d . . . . .
H9 H 0.1188 0.3430 0.5132 0.025 Uiso 1 1 calc R U . . .
F1 F 0.23817(12) 0.26693(13) 0.14557(12) 0.0449(3) Uani 1 1 d . . . . .
C10 C 0.24377(10) 0.41549(10) 0.65696(9) 0.01263(14) Uani 1 1 d . . . . .
C11 C 0.38164(12) 0.33220(12) 0.63845(11) 0.0201(2) Uani 1 1 d . . . . .
H11 H 0.4618 0.3724 0.5616 0.024 Uiso 1 1 calc R U . . .
C12 C 0.40310(11) 0.19081(12) 0.73131(11) 0.01947(19) Uani 1 1 d . . . . .
H12 H 0.4974 0.1349 0.7188 0.023 Uiso 1 1 calc R U . . .
C13 C 0.28468(10) 0.13314(10) 0.84206(9) 0.01239(14) Uani 1 1 d . . . . .
C14 C 0.14480(11) 0.21175(12) 0.86023(10) 0.01705(17) Uani 1 1 d . . . . .
H14 H 0.0639 0.1696 0.9355 0.020 Uiso 1 1 calc R U . . .
C15 C 0.12481(11) 0.35271(12) 0.76701(10) 0.01695(17) Uani 1 1 d . . . . .
H15 H 0.0295 0.4067 0.7783 0.020 Uiso 1 1 calc R U . . .
S1 S 0.30851(3) -0.04484(3) 0.96157(2) 0.01283(5) Uani 1 1 d . . . . .
O2 O 0.46222(9) -0.09973(9) 0.91889(9) 0.01859(14) Uani 1 1 d . . . . .
O3 O 0.19812(10) -0.13665(9) 0.98438(9) 0.01965(15) Uani 1 1 d . . . . .
N2 N 0.26791(12) -0.00825(11) 1.09225(9) 0.01856(16) Uani 1 1 d . . . . .
H2A H 0.233(2) -0.082(2) 1.1649(19) 0.028(5) Uiso 1 1 d . . . . .
H2B H 0.341(3) 0.028(3) 1.094(2) 0.044(6) Uiso 1 1 d . . . . .
Si1 Si 0.22326(3) 0.76473(3) 0.70364(3) 0.01571(6) Uani 1 1 d . . . . .
C16 C 0.42193(16) 0.7855(2) 0.66517(19) 0.0393(4) Uani 1 1 d . . . . .
H16A H 0.4332 0.8204 0.7281 0.059 Uiso 1 1 calc R U . . .
H16B H 0.4581 0.8586 0.5756 0.059 Uiso 1 1 calc R U . . .
H16C H 0.4796 0.6886 0.6715 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1478(2) 0.62186(18) 0.86853(13) 0.0404(4) Uani 1 1 d . . . . .
H17A H 0.0467 0.6058 0.8801 0.061 Uiso 1 1 calc R U . . .
H17B H 0.1457 0.6565 0.9364 0.061 Uiso 1 1 calc R U . . .
H17C H 0.2111 0.5276 0.8764 0.061 Uiso 1 1 calc R U . . .
C18 C 0.11055(19) 0.94722(17) 0.68526(17) 0.0349(3) Uani 1 1 d . . . . .
H18A H 0.1035 0.9780 0.7568 0.052 Uiso 1 1 calc R U . . .
H18B H 0.0107 0.9373 0.6889 0.052 Uiso 1 1 calc R U . . .
H18C H 0.1579 1.0228 0.6004 0.052 Uiso 1 1 calc R U . . .


_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
N1 C1 1.3168(16) .
N1 O1 1.4001(15) .
O1 C3 1.3683(15) .
C1 C2 1.4315(17) .
C1 C4 1.4712(16) .
C2 C3 1.3690(16) .
C2 C10 1.4804(16) .
C3 Si1 1.9018(15) .
C4 C9 1.3953(18) .
C4 C5 1.4030(19) .
C5 C6 1.3866(19) .
C5 H5 0.9500 .
C6 C7 1.371(2) .
C6 H6 0.9500 .
C7 F1 1.3522(16) .
C7 C8 1.382(2) .
C8 C9 1.3897(19) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C15 1.3959(16) .
C10 C11 1.3962(16) .
C11 C12 1.3940(17) .
C11 H11 0.9500 .
C12 C13 1.3851(16) .
C12 H12 0.9500 .
C13 C14 1.3920(15) .
C13 S1 1.7616(14) .
C14 C15 1.3902(16) .
C14 H14 0.9500 .
C15 H15 0.9500 .
S1 O3 1.4371(11) .
S1 O2 1.4427(11) .
S1 N2 1.6081(15) .
N2 H2A 0.87(2) .
N2 H2B 0.87(2) .
Si1 C17 1.8498(18) .
Si1 C16 1.8513(19) .
Si1 C18 1.8539(17) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .

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
C1 N1 O1 106.06(9) . .
C3 O1 N1 109.50(10) . .
N1 C1 C2 111.10(10) . .
N1 C1 C4 118.94(10) . .
C2 C1 C4 129.96(10) . .
C3 C2 C1 104.95(9) . .
C3 C2 C10 127.60(10) . .
C1 C2 C10 127.39(9) . .
O1 C3 C2 108.37(10) . .
O1 C3 Si1 114.89(9) . .
C2 C3 Si1 136.49(8) . .
C9 C4 C5 119.56(11) . .
C9 C4 C1 121.23(11) . .
C5 C4 C1 119.16(11) . .
C6 C5 C4 120.33(13) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C7 C6 C5 118.54(13) . .
C7 C6 H6 120.7 . .
C5 C6 H6 120.7 . .
F1 C7 C6 119.07(15) . .
F1 C7 C8 118.05(15) . .
C6 C7 C8 122.87(12) . .
C7 C8 C9 118.59(13) . .
C7 C8 H8 120.7 . .
C9 C8 H8 120.7 . .
C8 C9 C4 120.08(13) . .
C8 C9 H9 120.0 . .
C4 C9 H9 120.0 . .
C15 C10 C11 119.18(10) . .
C15 C10 C2 120.81(9) . .
C11 C10 C2 120.01(9) . .
C12 C11 C10 120.80(10) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C13 C12 C11 118.89(10) . .
C13 C12 H12 120.6 . .
C11 C12 H12 120.6 . .
C12 C13 C14 121.32(10) . .
C12 C13 S1 119.97(8) . .
C14 C13 S1 118.70(8) . .
C15 C14 C13 119.24(9) . .
C15 C14 H14 120.4 . .
C13 C14 H14 120.4 . .
C14 C15 C10 120.49(10) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
O3 S1 O2 117.15(7) . .
O3 S1 N2 107.05(6) . .
O2 S1 N2 112.55(6) . .
O3 S1 C13 109.43(6) . .
O2 S1 C13 107.05(6) . .
N2 S1 C13 102.63(7) . .
S1 N2 H2A 113.7(13) . .
S1 N2 H2B 112.1(15) . .
H2A N2 H2B 112.4(19) . .
C17 Si1 C16 112.40(10) . .
C17 Si1 C18 111.24(10) . .
C16 Si1 C18 111.12(9) . .
C17 Si1 C3 108.60(8) . .
C16 Si1 C3 106.21(7) . .
C18 Si1 C3 106.97(7) . .
Si1 C16 H16A 109.5 . .
Si1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
Si1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
Si1 C17 H17A 109.5 . .
Si1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
Si1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
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 . .

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
C1 N1 O1 C3 -0.78(11) . . . .
O1 N1 C1 C2 1.19(11) . . . .
O1 N1 C1 C4 -179.36(9) . . . .
N1 C1 C2 C3 -1.17(12) . . . .
C4 C1 C2 C3 179.47(10) . . . .
N1 C1 C2 C10 -178.52(9) . . . .
C4 C1 C2 C10 2.11(17) . . . .
N1 O1 C3 C2 0.06(11) . . . .
N1 O1 C3 Si1 175.29(7) . . . .
C1 C2 C3 O1 0.63(11) . . . .
C10 C2 C3 O1 177.97(9) . . . .
C1 C2 C3 Si1 -173.09(9) . . . .
C10 C2 C3 Si1 4.26(17) . . . .
N1 C1 C4 C9 -142.35(11) . . . .
C2 C1 C4 C9 36.97(16) . . . .
N1 C1 C4 C5 35.11(15) . . . .
C2 C1 C4 C5 -145.56(11) . . . .
C9 C4 C5 C6 2.03(17) . . . .
C1 C4 C5 C6 -175.48(11) . . . .
C4 C5 C6 C7 -0.89(18) . . . .
C5 C6 C7 F1 178.25(11) . . . .
C5 C6 C7 C8 -0.8(2) . . . .
F1 C7 C8 C9 -177.79(11) . . . .
C6 C7 C8 C9 1.24(19) . . . .
C7 C8 C9 C4 -0.05(17) . . . .
C5 C4 C9 C8 -1.55(17) . . . .
C1 C4 C9 C8 175.91(10) . . . .
C3 C2 C10 C15 74.61(15) . . . .
C1 C2 C10 C15 -108.62(13) . . . .
C3 C2 C10 C11 -105.74(13) . . . .
C1 C2 C10 C11 71.04(15) . . . .
C15 C10 C11 C12 -2.97(18) . . . .
C2 C10 C11 C12 177.37(11) . . . .
C10 C11 C12 C13 0.70(19) . . . .
C11 C12 C13 C14 1.71(18) . . . .
C11 C12 C13 S1 -179.70(9) . . . .
C12 C13 C14 C15 -1.78(17) . . . .
S1 C13 C14 C15 179.61(9) . . . .
C13 C14 C15 C10 -0.56(17) . . . .
C11 C10 C15 C14 2.89(17) . . . .
C2 C10 C15 C14 -177.45(10) . . . .
C12 C13 S1 O3 -126.22(10) . . . .
C14 C13 S1 O3 52.41(11) . . . .
C12 C13 S1 O2 1.69(11) . . . .
C14 C13 S1 O2 -179.68(8) . . . .
C12 C13 S1 N2 120.35(10) . . . .
C14 C13 S1 N2 -61.02(10) . . . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O3 0.95 2.41 3.239(2) 145.2 2_557
N2 H2A N1 0.87(2) 2.22(2) 3.043(2) 158.4(17) 1_546
N2 H2B O2 0.87(2) 2.12(2) 2.984(2) 172(2) 2_657

_refine_diff_density_max         0.725
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.080

_shelxl_version_number           2014-1

