Palladacycle-catalyzed Suzuki-Miyaura reaction of aryl/heteroaryl halides with MIDA boronates in EtOH/H2O or H2O
Li, Yabo; Wang, Jingran; Wang, Zhiwei; Huang, Mengmeng; Yan, Beiqi; Cui, Xiuling; Wu, Yusheng; Wu, Yangjie; RSC Advances  (2014) –; doi:10.1039/C4RA07486F

data_7217634
_publ_section_title
;
 Palladacycle-catalyzed Suzuki-Miyaura reaction of aryl/heteroaryl halides
 with MIDA boronates in EtOH/H2O or H2O
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA07486F
_journal_year                    2014
_chemical_formula_moiety         'C10 H6 N2 O S'
_chemical_formula_sum            'C10 H6 N2 O S'
_chemical_formula_weight         202.23
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-18
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.043(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3001(8)
_cell_length_b                   3.9310(2)
_cell_length_c                   20.1304(16)
_cell_measurement_reflns_used    917
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.2700
_cell_measurement_theta_min      4.3570
_cell_volume                     890.74(11)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -23.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 36

  2 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 26

  3 omega  -10.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000  -30.0000 25

  4 omega  -44.00   30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 74

  5 omega -109.00  -25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000  -90.0000 84

  6 omega  -90.00  -65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000  -30.0000 25

  7 omega -110.00  -73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000   90.0000 37

  8 omega   87.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  163.0000   14.0000 39

  9 omega   40.00   76.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 36

 10 omega   48.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 47

 11 omega   77.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 28

 12 omega   60.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 46

 13 omega   82.00  133.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 51

 14 omega   53.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 26

 15 omega   43.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 42

 16 omega   40.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 26

 17 omega   40.00  153.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 113

 18 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 46

 19 omega   26.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -150.0000 100

 20 omega   18.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   60.0000 82

 21 omega   26.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  120.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0084648000
_diffrn_orient_matrix_UB_12      -0.0620804000
_diffrn_orient_matrix_UB_13      -0.0758493000
_diffrn_orient_matrix_UB_21      -0.1364056000
_diffrn_orient_matrix_UB_22      -0.0153264000
_diffrn_orient_matrix_UB_23      -0.0013669000
_diffrn_orient_matrix_UB_31      -0.0067196000
_diffrn_orient_matrix_UB_32      0.3865975000
_diffrn_orient_matrix_UB_33      -0.0122504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2612
_diffrn_reflns_theta_full        72.63
_diffrn_reflns_theta_max         72.63
_diffrn_reflns_theta_min         4.33
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88880
_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_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1507P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1945
_reflns_number_gt                2107
_reflns_number_total             2612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra07486f2.cif
_cod_data_source_block           201309150_twin1_hklf4
_cod_database_code               7217634
_chemical_oxdiff_formula         C20H20S1