Palladium-catalyzed microwave-assisted direct arylation of imidazo[2,1-b]thiazoles with aryl bromides: synthesis and mechanistic study.
Zhu, Yi-Shuo; Shi, Benyi; Fang, Ran; Wang, Xiaoxuan; Jing, Huanwang; Organic & biomolecular chemistry 12 (2014) 5773–5780; doi:10.1039/c4ob00600c

data_7153872
_publ_section_title
;
 Palladium-catalyzed microwave-assisted direct arylation of
 imidazo[2,1-b]thiazoles with aryl bromides: synthesis and mechanistic
 study.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5773
_journal_page_last               5780
_journal_paper_doi               10.1039/c4ob00600c
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H11 N3 O2 S'
_chemical_formula_sum            'C17 H11 N3 O2 S'
_chemical_formula_weight         321.35
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   18.3921(7)
_cell_length_b                   18.3921(7)
_cell_length_c                   23.2883(17)
_cell_measurement_reflns_used    3773
_cell_measurement_temperature    296.24(11)
_cell_measurement_theta_max      27.4180
_cell_measurement_theta_min      3.4890
_cell_volume                     6822.3(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      296.24(11)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8882
_diffrn_measurement_details
;
  1 omega   76.00  101.60   0.8000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000    0.0000 32

  2 omega   38.00   64.40   0.8000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512 -178.0000   60.0000 33

  3 omega  -23.00   83.40   0.8000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000 -150.0000 133
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0119118000
_diffrn_orient_matrix_UB_12      -0.0037068000
_diffrn_orient_matrix_UB_13      -0.0283352000
_diffrn_orient_matrix_UB_21      -0.0357255000
_diffrn_orient_matrix_UB_22      -0.0407283000
_diffrn_orient_matrix_UB_23      -0.0021674000
_diffrn_orient_matrix_UB_31      -0.0237728000
_diffrn_orient_matrix_UB_32      0.0176199000
_diffrn_orient_matrix_UB_33      -0.0109654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18450
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2988
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       0.00008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1244
_refine_ls_number_reflns         11422
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                6917
_reflns_number_total             11422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00600c2.cif
_cod_data_source_block           shiby0510
_cod_depositor_comments          'Adding full bibliography for 7153872.cif.'
_cod_database_code               7153872
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(N6) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(N12) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(N15) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26),
  C27(H27), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C43(H43), C44(H44), C47(H47), C48(H48), C50(H50),
  C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C60(H60),
 C61(H61), C64(H64), C65(H65), C67(H67), C68(H68), C69(H69), C70(H70), C71(H71),
  C72(H72), C73(H73), C77(H77), C78(H78), C81(H81), C82(H82), C84(H84),
 C85(H85), C86(H86), C87(H87), C88(H88), C89(H89), C90(H90), C94(H94), C95(H95),
  C98(H98), C99(H99), C101(H101), C102(H102)
;