#------------------------------------------------------------------------------
#$Date: 2021-09-11 01:11:33 +0300 (Sat, 11 Sep 2021) $
#$Revision: 269091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564611.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1564611
loop_
_publ_author_name
'Schwärzer, Kuno'
'Rout, Saroj K.'
'Bessinger, Derya'
'Lima, Fabio'
'Brocklehurst, Cara E.'
'Karaghiosoff, Konstantin'
'Bein, Thomas'
'Knochel, Paul'
_publ_section_title
;
 Selective functionalization of the 1H-imidazo[1,2-b]pyrazole scaffold. A
 new potential non-classical isostere of indole and a precursor of
 push--pull dyes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04155J
_journal_year                    2021
_chemical_formula_moiety         'C12 H21 N3 O S Si'
_chemical_formula_sum            'C12 H21 N3 O S Si'
_chemical_formula_weight         283.47
_chemical_name_systematic
;
7-(methylthio)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[1,2-b]pyrazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-07-18 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.656(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4782(12)
_cell_length_b                   8.4222(7)
_cell_length_c                   12.5728(9)
_cell_measurement_reflns_used    1071
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      22.4350
_cell_measurement_theta_min      2.7550
_cell_volume                     1599.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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).
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0972
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10569
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.769
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80050
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       platelet
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0269P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1968
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04155j2.cif
_cod_data_source_block           test1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1564611
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.995
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'
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 . . .
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'
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_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_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) . . . . ?
