#------------------------------------------------------------------------------
#$Date: 2022-07-23 06:10:06 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245203.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_7245203
loop_
_publ_author_name
'Zhou, Zitong'
'Luo, Danyang'
'Li, Guanrong'
'Yang, Zhongtao'
'Cui, Liao'
'Yang, Weiguang'
_publ_section_title
;
 Copper-catalyzed three-component reaction to synthesize polysubstituted
 imidazo[1,2-a]pyridines
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              20199
_journal_page_last               20205
_journal_paper_doi               10.1039/D2RA02722D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C17 H17 N3 O4 S'
_chemical_formula_sum            'C17 H17 N3 O4 S'
_chemical_formula_weight         359.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                93.835(2)
_cell_angle_beta                 111.598(2)
_cell_angle_gamma                96.227(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7875(5)
_cell_length_b                   8.8129(5)
_cell_length_c                   11.7354(6)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      3.167
_cell_volume                     834.41(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17497
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         3.167
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0494 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0614P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3202
_reflns_number_total             3842
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra02722d3.cif
_cod_data_source_block           111
_cod_database_code               7245203
_shelx_shelxl_version_number     2018/3
_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_max   0.967
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C14(H14), C13(H13), C4(H4), C6(H6), C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.32291(5) 0.83090(4) 0.31410(3) 0.04545(14) Uani 1 1 d . . . . .
O4 O 0.16821(14) 0.29000(11) -0.05570(10) 0.0446(3) Uani 1 1 d . . . . .
N3 N 0.32338(14) 0.58409(12) -0.07180(10) 0.0328(2) Uani 1 1 d . . . . .
O2 O 0.32679(17) 0.97473(13) 0.26692(12) 0.0579(3) Uani 1 1 d . . . . .
O3 O 0.13010(15) 0.38476(13) 0.11352(10) 0.0493(3) Uani 1 1 d . . . . .
O1 O 0.22347(18) 0.79441(17) 0.38350(12) 0.0639(4) Uani 1 1 d . . . . .
N1 N 0.25236(17) 0.69541(15) 0.19713(12) 0.0448(3) Uani 1 1 d . . . . .
H1 H 0.178148 0.624154 0.198427 0.054 Uiso 1 1 calc R . . . .
N2 N 0.38136(16) 0.79729(13) 0.06343(11) 0.0401(3) Uani 1 1 d . . . . .
C8 C 0.29864(17) 0.68254(16) 0.09636(12) 0.0353(3) Uani 1 1 d . . . . .
C15 C 0.18009(17) 0.40214(16) 0.03036(13) 0.0377(3) Uani 1 1 d . . . . .
C10 C 0.39513(17) 0.73657(15) -0.03973(13) 0.0347(3) Uani 1 1 d . . . . .
C5 C 0.5261(2) 0.80098(17) 0.39993(13) 0.0435(3) Uani 1 1 d . . . . .
C9 C 0.26019(17) 0.54743(16) 0.01743(12) 0.0349(3) Uani 1 1 d . . . . .
C11 C 0.46806(19) 0.80612(17) -0.11481(14) 0.0404(3) Uani 1 1 d . . . . .
H11 H 0.516080 0.908623 -0.095436 0.049 Uiso 1 1 calc R . . . .
C12 C 0.4677(2) 0.72179(18) -0.21636(14) 0.0442(3) Uani 1 1 d . . . . .
H12 H 0.516308 0.766685 -0.266516 0.053 Uiso 1 1 calc R . . . .
C14 C 0.32304(19) 0.49964(16) -0.17450(13) 0.0406(3) Uani 1 1 d . . . . .
H14 H 0.274407 0.397336 -0.194618 0.049 Uiso 1 1 calc R . . . .
C16 C 0.1002(2) 0.13716(16) -0.04354(15) 0.0450(4) Uani 1 1 d . . . . .
H16A H -0.013272 0.135183 -0.050012 0.054 Uiso 1 1 calc R . . . .
H16B H 0.164460 0.106080 0.035771 0.054 Uiso 1 1 calc R . . . .
C13 C 0.3943(2) 0.56721(18) -0.24580(14) 0.0453(4) Uani 1 1 d . . . . .
H13 H 0.394831 0.510705 -0.315447 0.054 Uiso 1 1 calc R . . . .
C4 C 0.5544(3) 0.7141(2) 0.49728(15) 0.0565(4) Uani 1 1 d . . . . .
H4 H 0.467323 0.674231 0.518525 0.068 Uiso 1 1 calc R . . . .
C6 C 0.6554(2) 0.8607(2) 0.36835(16) 0.0554(4) Uani 1 1 d . . . . .
H6 H 0.636680 0.921259 0.303900 0.066 Uiso 1 1 calc R . . . .
C17 C 0.1079(3) 0.0317(2) -0.14619(18) 0.0576(4) Uani 1 1 d . . . . .
H17A H 0.042951 0.063161 -0.224025 0.086 Uiso 1 1 calc GR . . . .
H17B H 0.065004 -0.071518 -0.141157 0.086 Uiso 1 1 calc GR . . . .
H17C H 0.220643 0.035728 -0.139176 0.086 Uiso 1 1 calc GR . . . .
C3 C 0.7131(3) 0.6872(3) 0.56271(17) 0.0674(5) Uani 1 1 d . . . . .
H3 H 0.732615 0.630312 0.629355 0.081 Uiso 1 1 calc R . . . .
C7 C 0.8124(2) 0.8295(2) 0.43362(18) 0.0632(5) Uani 1 1 d . . . . .
H7 H 0.899069 0.867524 0.411267 0.076 Uiso 1 1 calc R . . . .
C2 C 0.8439(3) 0.7431(2) 0.53127(16) 0.0613(5) Uani 1 1 d . . . . .
C1 C 1.0172(3) 0.7102(3) 0.6013(2) 0.0932(8) Uani 1 1 d . . . . .
H1A H 1.014883 0.639543 0.659657 0.140 Uiso 1 1 calc GR . . . .
H1B H 1.086726 0.804242 0.644316 0.140 Uiso 1 1 calc GR . . . .
H1C H 1.060163 0.665995 0.544479 0.140 Uiso 1 1 calc GR . . . .
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'
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
O2 S1 O1 120.85(8) . . ?
O2 S1 N1 108.08(7) . . ?
O2 S1 C5 109.20(8) . . ?
O1 S1 N1 103.55(8) . . ?
O1 S1 C5 108.49(8) . . ?
N1 S1 C5 105.57(7) . . ?
C15 O4 C16 116.82(11) . . ?
C10 N3 C9 106.21(11) . . ?
C14 N3 C10 121.63(12) . . ?
C14 N3 C9 132.15(12) . . ?
S1 N1 H1 116.3 . . ?
C8 N1 S1 127.45(11) . . ?
C8 N1 H1 116.3 . . ?
C8 N2 C10 104.56(12) . . ?
N1 C8 C9 122.44(13) . . ?
N2 C8 N1 124.49(13) . . ?
N2 C8 C9 113.06(12) . . ?
O4 C15 C9 113.50(12) . . ?
O3 C15 O4 123.99(13) . . ?
O3 C15 C9 122.51(13) . . ?
N3 C10 C11 118.96(13) . . ?
N2 C10 N3 111.89(12) . . ?
N2 C10 C11 129.15(13) . . ?
C4 C5 S1 119.14(14) . . ?
C4 C5 C6 120.49(17) . . ?
C6 C5 S1 120.35(13) . . ?
N3 C9 C15 128.83(13) . . ?
C8 C9 N3 104.28(11) . . ?
C8 C9 C15 126.83(13) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.17(13) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.31(14) . . ?
C13 C12 H12 119.8 . . ?
N3 C14 H14 120.5 . . ?
C13 C14 N3 119.01(13) . . ?
C13 C14 H14 120.5 . . ?
O4 C16 H16A 110.4 . . ?
O4 C16 H16B 110.4 . . ?
O4 C16 C17 106.62(13) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.92(14) . . ?
C14 C13 H13 119.5 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.24(18) . . ?
C3 C4 H4 120.4 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.13(17) . . ?
C7 C6 H6 120.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C3 H3 119.3 . . ?
C4 C3 C2 121.33(18) . . ?
C2 C3 H3 119.3 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C2 121.49(19) . . ?
C2 C7 H7 119.3 . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C3 118.30(18) . . ?
C7 C2 C1 120.5(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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 O2 1.4188(13) . ?
S1 O1 1.4243(13) . ?
S1 N1 1.6394(13) . ?
S1 C5 1.7569(17) . ?
O4 C15 1.3319(18) . ?
O4 C16 1.4510(17) . ?
N3 C10 1.3852(17) . ?
N3 C9 1.3940(17) . ?
N3 C14 1.3724(18) . ?
O3 C15 1.2207(18) . ?
N1 H1 0.8600 . ?
N1 C8 1.3866(18) . ?
N2 C8 1.3418(18) . ?
N2 C10 1.3423(18) . ?
C8 C9 1.3874(19) . ?
C15 C9 1.4377(19) . ?
C10 C11 1.4020(19) . ?
C5 C4 1.379(2) . ?
C5 C6 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.360(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.405(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.348(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.498(2) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.378(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.378(3) . ?
C2 C1 1.512(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
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 C8 N2 -16.2(2) . . . . ?
S1 N1 C8 C9 164.94(12) . . . . ?
S1 C5 C4 C3 178.33(14) . . . . ?
S1 C5 C6 C7 -176.98(14) . . . . ?
O4 C15 C9 N3 0.6(2) . . . . ?
O4 C15 C9 C8 -176.15(13) . . . . ?
N3 C10 C11 C12 -0.6(2) . . . . ?
N3 C14 C13 C12 -0.2(2) . . . . ?
O2 S1 N1 C8 45.84(15) . . . . ?
O2 S1 C5 C4 150.24(13) . . . . ?
O2 S1 C5 C6 -31.27(16) . . . . ?
O3 C15 C9 N3 179.86(14) . . . . ?
O3 C15 C9 C8 3.1(2) . . . . ?
O1 S1 N1 C8 175.15(13) . . . . ?
O1 S1 C5 C4 16.70(16) . . . . ?
O1 S1 C5 C6 -164.82(14) . . . . ?
N1 S1 C5 C4 -93.77(14) . . . . ?
N1 S1 C5 C6 84.72(14) . . . . ?
N1 C8 C9 N3 178.22(12) . . . . ?
N1 C8 C9 C15 -4.4(2) . . . . ?
N2 C8 C9 N3 -0.74(16) . . . . ?
N2 C8 C9 C15 176.65(13) . . . . ?
N2 C10 C11 C12 -179.89(15) . . . . ?
C8 N2 C10 N3 -0.58(16) . . . . ?
C8 N2 C10 C11 178.77(15) . . . . ?
C15 O4 C16 C17 -177.14(13) . . . . ?
C10 N3 C9 C8 0.34(14) . . . . ?
C10 N3 C9 C15 -176.98(14) . . . . ?
C10 N3 C14 C13 -0.1(2) . . . . ?
C10 N2 C8 N1 -178.11(13) . . . . ?
C10 N2 C8 C9 0.83(16) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C5 S1 N1 C8 -70.91(14) . . . . ?
C5 C4 C3 C2 -1.2(3) . . . . ?
C5 C6 C7 C2 -1.5(3) . . . . ?
C9 N3 C10 N2 0.15(15) . . . . ?
C9 N3 C10 C11 -179.28(12) . . . . ?
C9 N3 C14 C13 179.57(14) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C14 N3 C10 N2 179.87(12) . . . . ?
C14 N3 C10 C11 0.4(2) . . . . ?
C14 N3 C9 C8 -179.34(14) . . . . ?
C14 N3 C9 C15 3.3(2) . . . . ?
C16 O4 C15 O3 -3.8(2) . . . . ?
C16 O4 C15 C9 175.44(12) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C4 C3 C2 C7 1.2(3) . . . . ?
C4 C3 C2 C1 -178.54(19) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C7 C2 C3 0.2(3) . . . . ?
C6 C7 C2 C1 179.93(19) . . . . ?
