# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 2097280'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-07-18 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
7-(methylthio)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[1,2-b]pyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H21 N3 O S Si'
_chemical_formula_sum            'C12 H21 N3 O S Si'
_chemical_formula_weight         283.47

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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4782(12)
_cell_length_b                   8.4222(7)
_cell_length_c                   12.5728(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.656(8)
_cell_angle_gamma                90
_cell_volume                     1599.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1071
_cell_measurement_theta_min      2.7550
_cell_measurement_theta_max      22.4350

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            10569
_diffrn_reflns_av_unetI/netI     0.0972
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3139
_reflns_number_gt                1968
_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       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0269P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3139
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
S1 S 0.13900(5) 0.81919(9) 0.42777(7) 0.0337(2) Uani 1 1 d . . . . .
C1 C 0.10979(18) 0.5663(4) 0.2738(2) 0.0312(8) Uani 1 1 d . . . . .
H1 H 0.1156(3) 0.6261(18) 0.2198(16) 0.037 Uiso 1 1 calc R U . . .
Si1 Si 0.39474(6) 0.21871(11) 0.86580(7) 0.0364(3) Uani 1 1 d . . . . .
O1 O 0.21582(12) 0.5268(2) 0.68181(14) 0.0274(5) Uani 1 1 d . . . . .
N3 N 0.10145(14) 0.4301(3) 0.53717(16) 0.0211(5) Uani 1 1 d . . . . .
C3 C 0.10540(17) 0.4901(3) 0.4368(2) 0.0196(6) Uani 1 1 d . . . . .
N2 N 0.08888(14) 0.3682(3) 0.36587(17) 0.0219(5) Uani 1 1 d . . . . .
C2 C 0.11965(17) 0.6252(3) 0.3798(2) 0.0226(6) Uani 1 1 d . . . . .
C4 C 0.08296(17) 0.2695(3) 0.5244(2) 0.0238(7) Uani 1 1 d . . . . .
H4 H 0.0776(2) 0.2000(19) 0.5801(15) 0.029 Uiso 1 1 calc R U . . .
C5 C 0.07402(17) 0.2297(3) 0.4190(2) 0.0263(7) Uani 1 1 d . . . . .
H5 H 0.0617(4) 0.138(3) 0.3904(9) 0.032 Uiso 1 1 calc R U . . .
N1 N 0.09075(15) 0.4111(3) 0.26146(17) 0.0284(6) Uani 1 1 d . . . . .
C8 C 0.24945(18) 0.3832(3) 0.7372(2) 0.0275(7) Uani 1 1 d . . . . .
H8A H 0.2392(3) 0.2936(15) 0.6853(8) 0.033 Uiso 1 1 calc R U . . .
H8B H 0.2175(5) 0.3607(5) 0.7956(10) 0.033 Uiso 1 1 calc R U . . .
C7 C 0.12411(18) 0.5192(3) 0.6386(2) 0.0273(7) Uani 1 1 d . . . . .
H7A H 0.1004(4) 0.6294(18) 0.6254(3) 0.033 Uiso 1 1 calc R U . . .
H7B H 0.0949(5) 0.4686(9) 0.6933(9) 0.033 Uiso 1 1 calc R U . . .
C9 C 0.34705(18) 0.3984(3) 0.7859(2) 0.0313(8) Uani 1 1 d . . . . .
H9A H 0.3565(3) 0.4877(16) 0.8320(8) 0.038 Uiso 1 1 calc R U . . .
H9B H 0.3772(6) 0.4155(5) 0.7295(10) 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2564(2) 0.8152(4) 0.4816(3) 0.0500(10) Uani 1 1 d . . . . .
H6A H 0.2699(3) 0.738(2) 0.5376(14) 0.075 Uiso 1 1 calc R U . . .
H6B H 0.2755(4) 0.9163(17) 0.5103(16) 0.075 Uiso 1 1 calc R U . . .
H6C H 0.2857(5) 0.789(2) 0.4253(10) 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3330(2) 0.1772(4) 0.9732(3) 0.0594(12) Uani 1 1 d . . . . .
H11A H 0.3575(11) 0.089(2) 1.0134(15) 0.089 Uiso 1 1 calc R U . . .
H11B H 0.2738(12) 0.157(3) 0.9410(6) 0.089 Uiso 1 1 calc R U . . .
H11C H 0.3365(13) 0.265(2) 1.0192(14) 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3847(3) 0.0428(5) 0.7741(3) 0.104(2) Uani 1 1 d . . . . .
H10A H 0.413(2) 0.0626(17) 0.720(2) 0.156 Uiso 1 1 calc R U . . .
H10B H 0.3266(14) 0.023(3) 0.745(2) 0.156 Uiso 1 1 calc R U . . .
H10C H 0.409(2) -0.043(2) 0.8128(11) 0.156 Uiso 1 1 calc R U . . .
C12 C 0.5122(2) 0.2549(5) 0.9289(3) 0.098(2) Uani 1 1 d . . . . .
H12A H 0.5164(3) 0.334(3) 0.975(2) 0.147 Uiso 1 1 calc R U . . .
H12B H 0.5410(9) 0.279(4) 0.8778(14) 0.147 Uiso 1 1 calc R U . . .
H12C H 0.5354(9) 0.169(3) 0.964(3) 0.147 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
_geom_bond_publ_flag
S1 C2 1.745(3) . ?
S1 C6 1.795(3) . ?
C1 N1 1.341(3) . ?
C1 C2 1.398(4) . ?
C1 H1 0.87(3) . ?
Si1 C12 1.843(4) . ?
Si1 C11 1.850(3) . ?
Si1 C10 1.862(4) . ?
Si1 C9 1.876(3) . ?
O1 C7 1.406(3) . ?
O1 C8 1.435(3) . ?
N3 C3 1.372(3) . ?
N3 C4 1.385(3) . ?
N3 C7 1.455(3) . ?
C3 N2 1.348(3) . ?
C3 C2 1.388(3) . ?
N2 N1 1.368(3) . ?
N2 C5 1.388(3) . ?
C4 C5 1.345(3) . ?
C4 H4 0.93(2) . ?
C5 H5 0.86(3) . ?
C8 C9 1.506(4) . ?
C8 H8A 0.988(16) . ?
C8 H8B 0.988(16) . ?
C7 H7A 0.998(16) . ?
C7 H7B 0.998(16) . ?
C9 H9A 0.941(16) . ?
C9 H9B 0.941(16) . ?
C6 H6A 0.947(15) . ?
C6 H6B 0.947(15) . ?
C6 H6C 0.947(15) . ?
C11 H11A 0.932(17) . ?
C11 H11B 0.932(17) . ?
C11 H11C 0.932(17) . ?
C10 H10A 0.91(2) . ?
C10 H10B 0.91(2) . ?
C10 H10C 0.91(2) . ?
C12 H12A 0.88(2) . ?
C12 H12B 0.88(2) . ?
C12 H12C 0.88(2) . ?

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
C2 S1 C6 101.28(14) . . ?
N1 C1 C2 115.6(3) . . ?
N1 C1 H1 122.2 . . ?
C2 C1 H1 122.2 . . ?
C12 Si1 C11 109.63(17) . . ?
C12 Si1 C10 109.8(2) . . ?
C11 Si1 C10 108.32(19) . . ?
C12 Si1 C9 109.42(15) . . ?
C11 Si1 C9 109.74(14) . . ?
C10 Si1 C9 109.90(16) . . ?
C7 O1 C8 112.2(2) . . ?
C3 N3 C4 107.6(2) . . ?
C3 N3 C7 124.4(2) . . ?
C4 N3 C7 127.5(2) . . ?
N2 C3 N3 106.7(2) . . ?
N2 C3 C2 108.1(2) . . ?
N3 C3 C2 145.1(3) . . ?
C3 N2 N1 113.1(2) . . ?
C3 N2 C5 110.4(2) . . ?
N1 N2 C5 136.4(2) . . ?
C3 C2 C1 101.8(2) . . ?
C3 C2 S1 128.6(2) . . ?
C1 C2 S1 129.5(2) . . ?
C5 C4 N3 109.4(2) . . ?
C5 C4 H4 125.3 . . ?
N3 C4 H4 125.3 . . ?
C4 C5 N2 105.8(2) . . ?
C4 C5 H5 127.1 . . ?
N2 C5 H5 127.1 . . ?
C1 N1 N2 101.3(2) . . ?
O1 C8 C9 110.5(2) . . ?
O1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O1 C7 N3 113.0(2) . . ?
O1 C7 H7A 109.0 . . ?
N3 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
N3 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C9 Si1 113.0(2) . . ?
C8 C9 H9A 109.0 . . ?
Si1 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
Si1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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 . . ?

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
C4 N3 C3 N2 0.5(3) . . . . ?
C7 N3 C3 N2 173.5(2) . . . . ?
C4 N3 C3 C2 -179.3(4) . . . . ?
C7 N3 C3 C2 -6.3(6) . . . . ?
N3 C3 N2 N1 -180.0(2) . . . . ?
C2 C3 N2 N1 -0.1(3) . . . . ?
N3 C3 N2 C5 0.1(3) . . . . ?
C2 C3 N2 C5 -179.9(2) . . . . ?
N2 C3 C2 C1 -0.2(3) . . . . ?
N3 C3 C2 C1 179.7(4) . . . . ?
N2 C3 C2 S1 176.87(19) . . . . ?
N3 C3 C2 S1 -3.3(6) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
N1 C1 C2 S1 -176.6(2) . . . . ?
C6 S1 C2 C3 84.8(3) . . . . ?
C6 S1 C2 C1 -99.0(3) . . . . ?
C3 N3 C4 C5 -1.0(3) . . . . ?
C7 N3 C4 C5 -173.8(2) . . . . ?
N3 C4 C5 N2 1.0(3) . . . . ?
C3 N2 C5 C4 -0.7(3) . . . . ?
N1 N2 C5 C4 179.4(3) . . . . ?
C2 C1 N1 N2 -0.4(3) . . . . ?
C3 N2 N1 C1 0.3(3) . . . . ?
C5 N2 N1 C1 -179.9(3) . . . . ?
C7 O1 C8 C9 -177.9(2) . . . . ?
C8 O1 C7 N3 -78.8(3) . . . . ?
C3 N3 C7 O1 -80.4(3) . . . . ?
C4 N3 C7 O1 91.3(3) . . . . ?
O1 C8 C9 Si1 177.12(16) . . . . ?
C12 Si1 C9 C8 -176.3(2) . . . . ?
C11 Si1 C9 C8 -56.0(3) . . . . ?
C10 Si1 C9 C8 63.0(3) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059

