#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:00:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178764 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/18/4101884.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_4101884
loop_
_publ_author_name
'Peihua Xi'
'Fan Yang'
'Song Qin'
'Dongbing Zhao'
'Jingbo Lan'
'Ge Gao'
'Changwei Hu'
'Jingsong You'
_publ_section_title
;
 Palladium(II)-Catalyzed Oxidative C-H/C-H Cross-Coupling of Heteroarenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1822
_journal_page_last               1824
_journal_paper_doi               10.1021/ja909807f
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C13 H12 N4 O3 S'
_chemical_formula_sum            'C13 H12 N4 O3 S'
_chemical_formula_weight         304.33
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.472(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2106(14)
_cell_length_b                   6.7252(12)
_cell_length_c                   12.488(2)
_cell_measurement_reflns_used    2303
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.010
_cell_measurement_theta_min      2.824
_cell_volume                     685.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3912
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.50
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.881277
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0454
_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/[σ²(Fo²)+(0.1019P)²+0.0655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                1236
_reflns_number_total             1467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909807f_si_001.cif
_cod_data_source_block           06181m
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4101884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.76349(8) 0.2500 0.39166(5) 0.0454(3) Uani 1 2 d S . .
O1 O 1.0051(3) 0.2500 0.2213(2) 0.0766(7) Uani 1 2 d S . .
O2 O 0.5775(3) 0.2500 0.96471(15) 0.0635(7) Uani 1 2 d S . .
O3 O 0.1216(2) 0.2500 0.71949(19) 0.0648(7) Uani 1 2 d S . .
N1 N 0.3611(2) 0.2500 0.54501(16) 0.0386(5) Uani 1 2 d S . .
N2 N 0.6320(3) 0.2500 0.59658(17) 0.0399(5) Uani 1 2 d S . .
N3 N 0.6188(3) 0.2500 0.78851(17) 0.0426(6) Uani 1 2 d S . .
N4 N 0.3521(3) 0.2500 0.84080(17) 0.0449(6) Uani 1 2 d S . .
C1 C 0.8618(4) 0.2500 0.1870(2) 0.0575(8) Uani 1 2 d S . .
H1A H 0.8354 0.2500 0.1126 0.069 Uiso 1 2 calc SR . .
C2 C 0.7261(4) 0.2500 0.2536(2) 0.0470(7) Uani 1 2 d S . .
C3 C 0.5633(4) 0.2500 0.2194(2) 0.0501(7) Uani 1 2 d S . .
H3A H 0.5212 0.2500 0.1471 0.060 Uiso 1 2 calc SR . .
C4 C 0.4638(4) 0.2500 0.3054(2) 0.0459(6) Uani 1 2 d S . .
H4A H 0.3498 0.2500 0.2961 0.055 Uiso 1 2 calc SR . .
C5 C 0.5569(3) 0.2500 0.40377(19) 0.0387(6) Uani 1 2 d S . .
C6 C 0.5132(3) 0.2500 0.5139(2) 0.0383(6) Uani 1 2 d S . .
C7 C 0.3838(3) 0.2500 0.6567(2) 0.0391(6) Uani 1 2 d S . .
C8 C 0.5492(3) 0.2500 0.68353(19) 0.0379(6) Uani 1 2 d S . .
C9 C 0.5203(3) 0.2500 0.8702(2) 0.0448(7) Uani 1 2 d S . .
C10 C 0.2706(3) 0.2500 0.7357(2) 0.0423(6) Uani 1 2 d S . .
C11 C 0.2027(4) 0.2500 0.4785(3) 0.0527(8) Uani 1 2 d S . .
H11A H 0.196(3) 0.139(3) 0.431(2) 0.066(7) Uiso 1 1 d . . .
H11B H 0.118(5) 0.2500 0.516(3) 0.067(11) Uiso 1 2 d S . .
C12 C 0.7973(4) 0.2500 0.8139(3) 0.0637(10) Uani 1 2 d S . .
H12B H 0.8245 0.1355 0.8583 0.076 Uiso 1 1 d R . .
H12A H 0.867(9) 0.2500 0.764(6) 0.18(3) Uiso 1 2 d S . .
C13 C 0.2517(5) 0.2500 0.9309(3) 0.0646(10) Uani 1 2 d S . .
H13A H 0.156(7) 0.2500 0.905(4) 0.115(19) Uiso 1 2 d S . .
H13B H 0.279(4) 0.118(5) 0.974(2) 0.113(11) Uiso 1 1 d . . .
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
C2 S C5 91.26(13) . . ?
C6 N1 C7 105.5(2) . . ?
C6 N1 C11 129.0(2) . . ?
C7 N1 C11 125.6(2) . . ?
C6 N2 C8 103.5(2) . . ?
C9 N3 C8 119.7(2) . . ?
C9 N3 C12 119.9(2) . . ?
C8 N3 C12 120.4(2) . . ?
C9 N4 C10 127.0(2) . . ?
C9 N4 C13 115.2(2) . . ?
C10 N4 C13 117.8(2) . . ?
O1 C1 C2 124.9(3) . . ?
O1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C3 C2 C1 127.4(3) . . ?
C3 C2 S 112.0(2) . . ?
C1 C2 S 120.7(2) . . ?
C2 C3 C4 113.1(2) . . ?
C2 C3 H3A 123.4 . . ?
C4 C3 H3A 123.4 . . ?
C5 C4 C3 111.5(3) . . ?
C5 C4 H4A 124.2 . . ?
C3 C4 H4A 124.2 . . ?
C4 C5 C6 132.3(2) . . ?
C4 C5 S 112.1(2) . . ?
C6 C5 S 115.61(19) . . ?
N2 C6 N1 113.3(2) . . ?
N2 C6 C5 119.5(2) . . ?
N1 C6 C5 127.2(2) . . ?
C8 C7 N1 105.3(2) . . ?
C8 C7 C10 122.6(2) . . ?
N1 C7 C10 132.1(2) . . ?
N2 C8 C7 112.5(2) . . ?
N2 C8 N3 125.4(2) . . ?
C7 C8 N3 122.1(2) . . ?
O2 C9 N3 121.6(2) . . ?
O2 C9 N4 121.2(2) . . ?
N3 C9 N4 117.1(2) . . ?
O3 C10 N4 121.3(2) . . ?
O3 C10 C7 127.2(3) . . ?
N4 C10 C7 111.5(2) . . ?
N1 C11 H11A 109.9(15) . . ?
N1 C11 H11B 114(2) . . ?
H11A C11 H11B 110(2) . . ?
N3 C12 H12B 106.7 . . ?
N3 C12 H12A 124(5) . . ?
H12B C12 H12A 106.0 . . ?
N4 C13 H13A 107(4) . . ?
N4 C13 H13B 106.8(17) . . ?
H13A C13 H13B 110(2) . . ?
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
S C2 1.717(3) . ?
S C5 1.720(3) . ?
O1 C1 1.206(4) . ?
O2 C9 1.221(3) . ?
O3 C10 1.217(3) . ?
N1 C6 1.349(3) . ?
N1 C7 1.387(3) . ?
N1 C11 1.462(3) . ?
N2 C6 1.338(3) . ?
N2 C8 1.344(3) . ?
N3 C9 1.371(3) . ?
N3 C8 1.370(3) . ?
N3 C12 1.465(4) . ?
N4 C9 1.388(4) . ?
N4 C10 1.405(3) . ?
N4 C13 1.468(3) . ?
C1 C2 1.464(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.357(5) . ?
C3 C4 1.421(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.459(3) . ?
C7 C8 1.362(4) . ?
C7 C10 1.429(4) . ?
C11 H11A 0.95(2) . ?
C11 H11B 0.88(4) . ?
C12 H12B 0.9599 . ?
C12 H12A 0.89(7) . ?
C13 H13A 0.82(6) . ?
C13 H13B 1.05(3) . ?
