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

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# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_fred53
_database_code_depnum_ccdc_archive 'CCDC 1584844'
_audit_update_record             
;
2017-11-09 deposited with the CCDC.
2018-05-07 downloaded from the CCDC.
;
_audit_creation_date             2017-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 N O3 S Si'
_chemical_formula_sum            'C21 H29 N O3 S Si'
_chemical_formula_weight         403.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2150 0.2490 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6959(3)
_cell_length_b                   16.0600(4)
_cell_length_c                   11.9522(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.9810(10)
_cell_angle_gamma                90
_cell_volume                     2243.71(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9643
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.725
_cell_measurement_theta_min      4.014
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1148 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8617. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized from DCM/Hexanes'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.809
_diffrn_reflns_theta_min         4.013
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4940
_reflns_number_total             5160
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0512(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+0.5877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1106
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.38310(3) 0.75403(2) 0.67682(3) 0.03301(12) Uani 1 1 d . . . . .
O1 O 0.26863(9) 0.73287(8) 0.64240(10) 0.0472(3) Uani 1 1 d . . . . .
N1 N 0.41769(8) 0.69516(6) 0.78496(8) 0.0277(2) Uani 1 1 d . . . . .
Si1 Si 0.80035(3) 0.59559(2) 0.77561(3) 0.02966(12) Uani 1 1 d . . . . .
C1 C 0.53229(10) 0.70807(7) 0.84252(10) 0.0265(2) Uani 1 1 d . . . . .
H1 H 0.581552 0.743702 0.795332 0.032 Uiso 1 1 calc R . . . .
O2 O 0.41030(10) 0.83728(6) 0.71090(9) 0.0477(3) Uani 1 1 d . . . . .
C2 C 0.58337(9) 0.61969(7) 0.85312(9) 0.0248(2) Uani 1 1 d . . . . .
H2 H 0.621846 0.611369 0.928313 0.030 Uiso 1 1 calc R . . . .
O3 O 0.65931(7) 0.60176(6) 0.76613(7) 0.0315(2) Uani 1 1 d . . . . .
C3 C 0.47997(10) 0.56463(7) 0.83903(9) 0.0258(2) Uani 1 1 d . . . . .
C4 C 0.46896(12) 0.48020(8) 0.86112(10) 0.0336(3) Uani 1 1 d . . . . .
H4 H 0.531444 0.449170 0.892307 0.040 Uiso 1 1 calc R . . . .
C5 C 0.36403(14) 0.44202(9) 0.83643(11) 0.0410(3) Uani 1 1 d . . . . .
H5 H 0.354395 0.384467 0.851838 0.049 Uiso 1 1 calc R . . . .
C6 C 0.27388(13) 0.48734(10) 0.78969(12) 0.0433(3) Uani 1 1 d . . . . .
H6 H 0.203477 0.459941 0.772396 0.052 Uiso 1 1 calc R . . . .
C7 C 0.28360(11) 0.57179(10) 0.76740(12) 0.0383(3) Uani 1 1 d . . . . .
H7 H 0.221142 0.602763 0.736057 0.046 Uiso 1 1 calc R . . . .
C8 C 0.38839(10) 0.60920(7) 0.79279(10) 0.0270(2) Uani 1 1 d . . . . .
C9 C 0.51574(13) 0.74941(8) 0.95533(12) 0.0386(3) Uani 1 1 d . . . . .
H9A H 0.476583 0.802852 0.944032 0.058 Uiso 1 1 calc GR . . . .
H9B H 0.590483 0.758802 0.992790 0.058 Uiso 1 1 calc GR . . . .
H9C H 0.469493 0.713199 1.001826 0.058 Uiso 1 1 calc GR . . . .
C10 C 0.47508(11) 0.72786(8) 0.56841(10) 0.0316(3) Uani 1 1 d . . . . .
C11 C 0.56454(14) 0.78075(10) 0.54463(12) 0.0429(3) Uani 1 1 d . . . . .
H11 H 0.576037 0.830747 0.585988 0.051 Uiso 1 1 calc R . . . .
C12 C 0.63728(15) 0.75981(12) 0.45957(14) 0.0518(4) Uani 1 1 d . . . . .
H12 H 0.699036 0.795566 0.442634 0.062 Uiso 1 1 calc R . . . .
C13 C 0.62016(15) 0.68771(13) 0.40005(13) 0.0517(4) Uani 1 1 d . . . . .
H13 H 0.670040 0.673984 0.341760 0.062 Uiso 1 1 calc R . . . .
C14 C 0.53103(15) 0.63468(11) 0.42390(12) 0.0475(4) Uani 1 1 d . . . . .
H14 H 0.520390 0.584664 0.382408 0.057 Uiso 1 1 calc R . . . .
C15 C 0.45696(13) 0.65446(9) 0.50853(11) 0.0375(3) Uani 1 1 d . . . . .
H15 H 0.395236 0.618570 0.525118 0.045 Uiso 1 1 calc R . . . .
C16 C 0.84810(14) 0.56149(15) 0.91902(13) 0.0588(5) Uani 1 1 d . . . . .
H16A H 0.838684 0.607482 0.971800 0.088 Uiso 1 1 calc GR . . . .
H16B H 0.928826 0.545167 0.918766 0.088 Uiso 1 1 calc GR . . . .
H16C H 0.801859 0.513923 0.941801 0.088 Uiso 1 1 calc GR . . . .
C17 C 0.86149(17) 0.69932(12) 0.7426(2) 0.0636(5) Uani 1 1 d . . . . .
H17A H 0.839917 0.739611 0.799691 0.095 Uiso 1 1 calc GR . . . .
H17B H 0.831692 0.717742 0.669031 0.095 Uiso 1 1 calc GR . . . .
H17C H 0.945047 0.695232 0.741593 0.095 Uiso 1 1 calc GR . . . .
C18 C 0.83793(11) 0.51547(9) 0.66862(11) 0.0352(3) Uani 1 1 d . . . . .
C19 C 0.78996(17) 0.43038(10) 0.70179(18) 0.0565(4) Uani 1 1 d . . . . .
H19A H 0.824837 0.413183 0.773859 0.085 Uiso 1 1 calc GR . . . .
H19B H 0.807574 0.389159 0.644432 0.085 Uiso 1 1 calc GR . . . .
H19C H 0.706851 0.434458 0.708253 0.085 Uiso 1 1 calc GR . . . .
C20 C 0.78601(14) 0.53847(12) 0.55366(12) 0.0475(4) Uani 1 1 d . . . . .
H20A H 0.702474 0.540384 0.557305 0.071 Uiso 1 1 calc GR . . . .
H20B H 0.807730 0.496608 0.498643 0.071 Uiso 1 1 calc GR . . . .
H20C H 0.814536 0.593162 0.531303 0.071 Uiso 1 1 calc GR . . . .
C21 C 0.96900(14) 0.51021(14) 0.66168(17) 0.0598(5) Uani 1 1 d . . . . .
H21A H 0.999035 0.564337 0.638813 0.090 Uiso 1 1 calc GR . . . .
H21B H 0.988831 0.467834 0.606624 0.090 Uiso 1 1 calc GR . . . .
H21C H 1.002521 0.495106 0.735172 0.090 Uiso 1 1 calc GR . . . .


_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
S1 O1 1.4279(11) . ?
S1 N1 1.6407(10) . ?
S1 O2 1.4302(11) . ?
S1 C10 1.7634(13) . ?
N1 C1 1.4997(14) . ?
N1 C8 1.4262(16) . ?
Si1 O3 1.6525(9) . ?
Si1 C16 1.8665(17) . ?
Si1 C17 1.8607(19) . ?
Si1 C18 1.8769(14) . ?
C1 H1 1.0000 . ?
C1 C2 1.5436(16) . ?
C1 C9 1.5212(17) . ?
C2 H2 1.0000 . ?
C2 O3 1.4201(13) . ?
C2 C3 1.5028(16) . ?
C3 C4 1.3883(17) . ?
C3 C8 1.3872(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3890(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.385(2) . ?
C10 C15 1.3915(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9500 . ?
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 C19 1.534(2) . ?
C18 C20 1.528(2) . ?
C18 C21 1.5405(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
_geom_angle_publ_flag
O1 S1 N1 107.04(6) . . ?
O1 S1 O2 120.11(7) . . ?
O1 S1 C10 108.74(6) . . ?
N1 S1 C10 107.55(5) . . ?
O2 S1 N1 105.55(6) . . ?
O2 S1 C10 107.26(7) . . ?
C1 N1 S1 118.28(8) . . ?
C8 N1 S1 123.79(8) . . ?
C8 N1 C1 108.46(9) . . ?
O3 Si1 C16 110.29(6) . . ?
O3 Si1 C17 108.77(8) . . ?
O3 Si1 C18 104.54(5) . . ?
C16 Si1 C18 110.79(8) . . ?
C17 Si1 C16 110.64(10) . . ?
C17 Si1 C18 111.62(8) . . ?
N1 C1 H1 110.1 . . ?
N1 C1 C2 104.34(9) . . ?
N1 C1 C9 109.14(10) . . ?
C2 C1 H1 110.1 . . ?
C9 C1 H1 110.1 . . ?
C9 C1 C2 112.91(10) . . ?
C1 C2 H2 110.9 . . ?
O3 C2 C1 112.11(9) . . ?
O3 C2 H2 110.9 . . ?
O3 C2 C3 108.65(9) . . ?
C3 C2 C1 102.95(9) . . ?
C3 C2 H2 110.9 . . ?
C2 O3 Si1 127.60(7) . . ?
C4 C3 C2 129.27(11) . . ?
C8 C3 C2 110.39(10) . . ?
C8 C3 C4 120.29(11) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.43(13) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.48(13) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.70(13) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.28(13) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 109.97(10) . . ?
C3 C8 C7 121.82(12) . . ?
C7 C8 N1 128.06(12) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 119.28(11) . . ?
C11 C10 C15 121.12(13) . . ?
C15 C10 S1 119.59(11) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.20(15) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.15(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.73(15) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.13(15) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.7 . . ?
C14 C15 C10 118.67(14) . . ?
C14 C15 H15 120.7 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 Si1 109.77(11) . . ?
C19 C18 C21 109.78(13) . . ?
C20 C18 Si1 110.60(10) . . ?
C20 C18 C19 108.06(14) . . ?
C20 C18 C21 109.27(13) . . ?
C21 C18 Si1 109.34(11) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
_geom_torsion_publ_flag
S1 N1 C1 C2 -131.15(8) . . . . ?
S1 N1 C1 C9 107.92(10) . . . . ?
S1 N1 C8 C3 138.75(9) . . . . ?
S1 N1 C8 C7 -45.65(17) . . . . ?
S1 C10 C11 C12 179.67(12) . . . . ?
S1 C10 C15 C14 -179.52(11) . . . . ?
O1 S1 N1 C1 -176.52(9) . . . . ?
O1 S1 N1 C8 41.03(11) . . . . ?
O1 S1 C10 C11 140.49(11) . . . . ?
O1 S1 C10 C15 -39.75(12) . . . . ?
N1 S1 C10 C11 -103.93(11) . . . . ?
N1 S1 C10 C15 75.83(11) . . . . ?
N1 C1 C2 O3 97.33(10) . . . . ?
N1 C1 C2 C3 -19.27(11) . . . . ?
C1 N1 C8 C3 -6.79(12) . . . . ?
C1 N1 C8 C7 168.81(12) . . . . ?
C1 C2 O3 Si1 106.93(10) . . . . ?
C1 C2 C3 C4 -166.53(12) . . . . ?
C1 C2 C3 C8 16.33(12) . . . . ?
O2 S1 N1 C1 -47.48(10) . . . . ?
O2 S1 N1 C8 170.07(10) . . . . ?
O2 S1 C10 C11 9.19(12) . . . . ?
O2 S1 C10 C15 -171.06(10) . . . . ?
C2 C3 C4 C5 -177.33(11) . . . . ?
C2 C3 C8 N1 -6.47(13) . . . . ?
C2 C3 C8 C7 177.60(11) . . . . ?
O3 Si1 C18 C19 -64.87(11) . . . . ?
O3 Si1 C18 C20 54.27(11) . . . . ?
O3 Si1 C18 C21 174.64(11) . . . . ?
O3 C2 C3 C4 74.44(14) . . . . ?
O3 C2 C3 C8 -102.71(11) . . . . ?
C3 C2 O3 Si1 -139.96(9) . . . . ?
C3 C4 C5 C6 0.84(19) . . . . ?
C4 C3 C8 N1 176.09(10) . . . . ?
C4 C3 C8 C7 0.16(17) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 N1 -175.43(12) . . . . ?
C6 C7 C8 C3 -0.29(19) . . . . ?
C8 N1 C1 C2 16.58(11) . . . . ?
C8 N1 C1 C9 -104.36(11) . . . . ?
C8 C3 C4 C5 -0.43(17) . . . . ?
C9 C1 C2 O3 -144.28(11) . . . . ?
C9 C1 C2 C3 99.12(11) . . . . ?
C10 S1 N1 C1 66.78(10) . . . . ?
C10 S1 N1 C8 -75.67(10) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C16 Si1 O3 C2 29.05(13) . . . . ?
C16 Si1 C18 C19 53.92(13) . . . . ?
C16 Si1 C18 C20 173.07(11) . . . . ?
C16 Si1 C18 C21 -66.56(13) . . . . ?
C17 Si1 O3 C2 -92.46(12) . . . . ?
C17 Si1 C18 C19 177.71(12) . . . . ?
C17 Si1 C18 C20 -63.14(13) . . . . ?
C17 Si1 C18 C21 57.23(14) . . . . ?
C18 Si1 O3 C2 148.19(10) . . . . ?

_olex2_date_sample_data_collection 2017-08-03
_olex2_date_sample_submission    2017-08-01
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id AJlb2P134a
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fred54
_database_code_depnum_ccdc_archive 'CCDC 1819482'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-05-07 downloaded from the CCDC.
;
_audit_creation_date             2018-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        '3-Bpin-5-F-2-Me-1-SO2Ph indoline'
_chemical_formula_moiety         'C21 H25 B F N O4 S'
_chemical_formula_sum            'C21 H25 B F N O4 S'
_chemical_formula_weight         417.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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'
B B 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0580 0.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5498(5)
_cell_length_b                   19.2550(9)
_cell_length_c                   10.4914(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.495(2)
_cell_angle_gamma                90
_cell_volume                     2053.72(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.728
_cell_measurement_theta_min      3.784
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    1.111
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1225 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.8143. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized from CDCl3/Hexane'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27426
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.715
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4109
_reflns_number_total             4699
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0084(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.9475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
B1 B 0.57880(16) 0.29229(9) 0.62618(18) 0.0303(3) Uani 1 1 d . . . . .
C1 C 0.83685(14) 0.27141(8) 0.69575(16) 0.0317(3) Uani 1 1 d . . . . .
H1 H 0.819063 0.273637 0.784632 0.038 Uiso 1 1 calc R . . . .
C2 C 0.70582(14) 0.26821(8) 0.58540(16) 0.0307(3) Uani 1 1 d . . . . .
H2 H 0.692624 0.221149 0.543634 0.037 Uiso 1 1 calc R . . . .
C3 C 0.72359(14) 0.32257(8) 0.48704(15) 0.0297(3) Uani 1 1 d . . . . .
C4 C 0.83432(14) 0.36339(8) 0.54091(15) 0.0302(3) Uani 1 1 d . . . . .
C5 C 0.86703(16) 0.41886(8) 0.47216(17) 0.0351(3) Uani 1 1 d . . . . .
H5 H 0.943623 0.445687 0.509048 0.042 Uiso 1 1 calc R . . . .
C6 C 0.78494(16) 0.43456(9) 0.34726(17) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.803984 0.472687 0.297951 0.044 Uiso 1 1 calc R . . . .
C7 C 0.67613(16) 0.39377(9) 0.29711(16) 0.0370(3) Uani 1 1 d . . . . .
C8 C 0.64266(15) 0.33791(9) 0.36299(16) 0.0347(3) Uani 1 1 d . . . . .
H8 H 0.566759 0.310821 0.324775 0.042 Uiso 1 1 calc R . . . .
C9 C 0.92901(16) 0.21144(9) 0.6907(2) 0.0415(4) Uani 1 1 d . . . . .
H9A H 0.887516 0.167608 0.704808 0.062 Uiso 1 1 calc GR . . . .
H9B H 1.011430 0.217456 0.760008 0.062 Uiso 1 1 calc GR . . . .
H9C H 0.947524 0.210570 0.604012 0.062 Uiso 1 1 calc GR . . . .
C10 C 0.89869(14) 0.44821(8) 0.83366(15) 0.0310(3) Uani 1 1 d . . . . .
C11 C 0.82501(17) 0.43123(9) 0.92113(17) 0.0389(4) Uani 1 1 d . . . . .
H11 H 0.825056 0.385122 0.953373 0.047 Uiso 1 1 calc R . . . .
C12 C 0.75138(18) 0.48266(10) 0.96063(18) 0.0429(4) Uani 1 1 d . . . . .
H12 H 0.700708 0.471657 1.020369 0.051 Uiso 1 1 calc R . . . .
C13 C 0.75123(16) 0.54968(10) 0.91375(17) 0.0399(4) Uani 1 1 d . . . . .
H13 H 0.700525 0.584510 0.941331 0.048 Uiso 1 1 calc R . . . .
C14 C 0.82446(19) 0.56619(9) 0.82701(18) 0.0426(4) Uani 1 1 d . . . . .
H14 H 0.824230 0.612399 0.795205 0.051 Uiso 1 1 calc R . . . .
C15 C 0.89847(17) 0.51553(9) 0.78606(17) 0.0380(4) Uani 1 1 d . . . . .
H15 H 0.948592 0.526798 0.725946 0.046 Uiso 1 1 calc R . . . .
C16 C 0.36379(14) 0.31676(9) 0.60936(16) 0.0339(3) Uani 1 1 d . . . . .
C17 C 0.45624(15) 0.36776(9) 0.70720(15) 0.0335(3) Uani 1 1 d . . . . .
C18 C 0.25775(17) 0.35168(12) 0.50186(18) 0.0492(5) Uani 1 1 d . . . . .
H18A H 0.199017 0.377980 0.542270 0.074 Uiso 1 1 calc GR . . . .
H18B H 0.207032 0.316291 0.442497 0.074 Uiso 1 1 calc GR . . . .
H18C H 0.298681 0.383318 0.451380 0.074 Uiso 1 1 calc GR . . . .
C19 C 0.30178(17) 0.26091(11) 0.6757(2) 0.0485(4) Uani 1 1 d . . . . .
H19A H 0.369791 0.239184 0.746820 0.073 Uiso 1 1 calc GR . . . .
H19B H 0.260785 0.225628 0.610339 0.073 Uiso 1 1 calc GR . . . .
H19C H 0.234799 0.281919 0.712719 0.073 Uiso 1 1 calc GR . . . .
C20 C 0.47603(19) 0.43652(9) 0.6434(2) 0.0464(4) Uani 1 1 d . . . . .
H20A H 0.499151 0.427581 0.560475 0.070 Uiso 1 1 calc GR . . . .
H20B H 0.547120 0.462591 0.703663 0.070 Uiso 1 1 calc GR . . . .
H20C H 0.394549 0.463648 0.625176 0.070 Uiso 1 1 calc GR . . . .
C21 C 0.42171(17) 0.37919(12) 0.83682(17) 0.0474(5) Uani 1 1 d . . . . .
H21A H 0.332976 0.398780 0.819206 0.071 Uiso 1 1 calc GR . . . .
H21B H 0.485014 0.411437 0.892033 0.071 Uiso 1 1 calc GR . . . .
H21C H 0.424813 0.334742 0.883059 0.071 Uiso 1 1 calc GR . . . .
F1 F 0.59606(11) 0.40959(7) 0.17474(10) 0.0529(3) Uani 1 1 d . . . . .
N1 N 0.90002(12) 0.33773(6) 0.66816(13) 0.0325(3) Uani 1 1 d . . . . .
O1 O 1.04198(12) 0.33686(6) 0.89359(12) 0.0441(3) Uani 1 1 d . . . . .
O2 O 1.08642(11) 0.41935(6) 0.72853(13) 0.0403(3) Uani 1 1 d . . . . .
O3 O 0.58426(10) 0.33228(6) 0.73417(11) 0.0327(3) Uani 1 1 d . . . . .
O4 O 0.45556(10) 0.28228(6) 0.54622(12) 0.0374(3) Uani 1 1 d . . . . .
S1 S 0.99536(3) 0.38388(2) 0.78560(4) 0.03306(13) 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
B1 C2 1.581(2) . ?
B1 O3 1.358(2) . ?
B1 O4 1.360(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.549(2) . ?
C1 C9 1.520(2) . ?
C1 N1 1.5039(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.516(2) . ?
C3 C4 1.396(2) . ?
C3 C8 1.384(2) . ?
C4 C5 1.383(2) . ?
C4 N1 1.418(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.374(2) . ?
C7 C8 1.375(2) . ?
C7 F1 1.3693(19) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.391(2) . ?
C10 C15 1.389(2) . ?
C10 S1 1.7617(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.560(2) . ?
C16 C18 1.517(2) . ?
C16 C19 1.521(2) . ?
C16 O4 1.4696(18) . ?
C17 C20 1.523(2) . ?
C17 C21 1.515(2) . ?
C17 O3 1.4720(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 S1 1.6301(13) . ?
O1 S1 1.4308(13) . ?
O2 S1 1.4336(12) . ?

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
O3 B1 C2 122.81(14) . . ?
O3 B1 O4 114.55(13) . . ?
O4 B1 C2 122.10(14) . . ?
C2 C1 H1 110.3 . . ?
C9 C1 H1 110.3 . . ?
C9 C1 C2 113.28(13) . . ?
N1 C1 H1 110.3 . . ?
N1 C1 C2 104.05(12) . . ?
N1 C1 C9 108.54(12) . . ?
B1 C2 H2 110.8 . . ?
C1 C2 B1 115.95(13) . . ?
C1 C2 H2 110.8 . . ?
C3 C2 B1 104.45(12) . . ?
C3 C2 C1 103.49(12) . . ?
C3 C2 H2 110.8 . . ?
C4 C3 C2 110.81(13) . . ?
C8 C3 C2 129.03(14) . . ?
C8 C3 C4 119.99(14) . . ?
C3 C4 N1 109.31(13) . . ?
C5 C4 C3 121.46(15) . . ?
C5 C4 N1 129.23(14) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.54(15) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.72(15) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C8 123.72(16) . . ?
F1 C7 C6 118.35(15) . . ?
F1 C7 C8 117.93(15) . . ?
C3 C8 H8 121.2 . . ?
C7 C8 C3 117.57(15) . . ?
C7 C8 H8 121.2 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 119.46(13) . . ?
C15 C10 C11 120.61(15) . . ?
C15 C10 S1 119.92(12) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.02(16) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.51(16) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.20(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.20(17) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.46(15) . . ?
C14 C15 H15 120.3 . . ?
C18 C16 C17 114.67(14) . . ?
C18 C16 C19 109.37(14) . . ?
C19 C16 C17 114.44(14) . . ?
O4 C16 C17 102.10(11) . . ?
O4 C16 C18 107.99(13) . . ?
O4 C16 C19 107.61(13) . . ?
C20 C17 C16 113.16(14) . . ?
C21 C17 C16 115.09(14) . . ?
C21 C17 C20 111.23(15) . . ?
O3 C17 C16 102.39(12) . . ?
O3 C17 C20 105.17(13) . . ?
O3 C17 C21 108.85(13) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 S1 122.21(11) . . ?
C4 N1 C1 110.28(12) . . ?
C4 N1 S1 124.70(10) . . ?
B1 O3 C17 105.70(12) . . ?
B1 O4 C16 107.12(12) . . ?
N1 S1 C10 108.19(7) . . ?
O1 S1 C10 108.73(8) . . ?
O1 S1 N1 105.42(7) . . ?
O1 S1 O2 120.35(8) . . ?
O2 S1 C10 106.76(7) . . ?
O2 S1 N1 106.92(7) . . ?

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
_geom_hbond_publ_flag
C5 H5 O2 0.95 2.44 3.044(2) 120.9 . yes
C6 H6 O2 0.95 2.43 3.311(2) 154.1 3_766 yes
C21 H21A O2 0.98 2.55 3.501(2) 163.3 1_455 yes

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
B1 C2 C3 C4 110.35(14) . . . . ?
B1 C2 C3 C8 -64.84(19) . . . . ?
C1 C2 C3 C4 -11.43(16) . . . . ?
C1 C2 C3 C8 173.38(15) . . . . ?
C1 N1 S1 C10 -93.95(12) . . . . ?
C1 N1 S1 O1 22.22(13) . . . . ?
C1 N1 S1 O2 151.40(11) . . . . ?
C2 B1 O3 C17 155.78(14) . . . . ?
C2 B1 O4 C16 -174.63(14) . . . . ?
C2 C1 N1 C4 -12.69(15) . . . . ?
C2 C1 N1 S1 149.12(11) . . . . ?
C2 C3 C4 C5 -176.66(13) . . . . ?
C2 C3 C4 N1 3.84(16) . . . . ?
C2 C3 C8 C7 174.97(14) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C3 C4 N1 C1 5.90(16) . . . . ?
C3 C4 N1 S1 -155.36(11) . . . . ?
C4 C3 C8 C7 0.2(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C4 N1 S1 C10 65.18(14) . . . . ?
C4 N1 S1 O1 -178.64(12) . . . . ?
C4 N1 S1 O2 -49.47(14) . . . . ?
C5 C4 N1 C1 -173.54(15) . . . . ?
C5 C4 N1 S1 25.2(2) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 F1 179.88(15) . . . . ?
C6 C7 C8 C3 0.3(2) . . . . ?
C8 C3 C4 C5 -1.0(2) . . . . ?
C8 C3 C4 N1 179.53(13) . . . . ?
C9 C1 C2 B1 142.55(14) . . . . ?
C9 C1 C2 C3 -103.73(14) . . . . ?
C9 C1 N1 C4 108.21(15) . . . . ?
C9 C1 N1 S1 -89.98(15) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C11 C10 S1 N1 81.40(14) . . . . ?
C11 C10 S1 O1 -32.60(15) . . . . ?
C11 C10 S1 O2 -163.84(13) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C15 C10 S1 N1 -99.78(14) . . . . ?
C15 C10 S1 O1 146.22(13) . . . . ?
C15 C10 S1 O2 14.98(15) . . . . ?
C16 C17 O3 B1 26.25(15) . . . . ?
C17 C16 O4 B1 19.00(16) . . . . ?
C18 C16 C17 C20 -31.07(19) . . . . ?
C18 C16 C17 C21 98.35(18) . . . . ?
C18 C16 C17 O3 -143.73(14) . . . . ?
C18 C16 O4 B1 140.23(15) . . . . ?
C19 C16 C17 C20 -158.64(14) . . . . ?
C19 C16 C17 C21 -29.21(19) . . . . ?
C19 C16 C17 O3 88.70(15) . . . . ?
C19 C16 O4 B1 -101.80(15) . . . . ?
C20 C17 O3 B1 -92.21(15) . . . . ?
C21 C17 O3 B1 148.51(15) . . . . ?
F1 C7 C8 C3 -179.55(14) . . . . ?
N1 C1 C2 B1 -99.77(14) . . . . ?
N1 C1 C2 C3 13.94(14) . . . . ?
N1 C4 C5 C6 -179.31(15) . . . . ?
O3 B1 C2 C1 19.2(2) . . . . ?
O3 B1 C2 C3 -93.93(17) . . . . ?
O3 B1 O4 C16 -2.90(18) . . . . ?
O4 B1 C2 C1 -169.72(14) . . . . ?
O4 B1 C2 C3 77.12(17) . . . . ?
O4 B1 O3 C17 -15.89(17) . . . . ?
O4 C16 C17 C20 85.42(15) . . . . ?
O4 C16 C17 C21 -145.15(14) . . . . ?
O4 C16 C17 O3 -27.24(14) . . . . ?
S1 C10 C11 C12 178.62(13) . . . . ?
S1 C10 C15 C14 -178.46(13) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id AJ3-09
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
