#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:04:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178767 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/21/4102126.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_4102126
loop_
_publ_author_name
'Bo Qian'
'Shengmei Guo'
'Jianping Shao'
'Qiming Zhu'
'Lei Yang'
'Chungu Xia'
'Hanmin Huang'
_publ_section_title
;
 Palladium-Catalyzed Benzylic Addition of 2-Methyl Azaarenes to N-Sulfonyl
 Aldimines via C-H Bond Activation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3650
_journal_page_last               3651
_journal_paper_doi               10.1021/ja910104n
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C18 H24 N2 O4 Pd'
_chemical_formula_weight         438.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.341(4)
_cell_angle_beta                 118.496(3)
_cell_angle_gamma                116.530(3)
_cell_formula_units_Z            1
_cell_length_a                   8.4123(6)
_cell_length_b                   8.5007(6)
_cell_length_c                   8.5524(6)
_cell_measurement_reflns_used    1686
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.79
_cell_volume                     461.86(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2547
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0286
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                1752
_reflns_number_total             1776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910104n_si_002.cif
_cod_data_source_block           p1
_cod_original_sg_symbol_H-M      'P 1'
_cod_database_code               4102126
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.0000 1.0000 0.0000 0.03210(13) Uani 1 2 d S . .
C7 C 0.4377(5) 1.0428(5) 0.1529(5) 0.0499(8) Uani 1 1 d . . .
H7A H 0.3345 0.9147 0.1100 0.075 Uiso 1 1 calc R . .
H7B H 0.5742 1.0583 0.1997 0.075 Uiso 1 1 calc R . .
H7C H 0.4034 1.0968 0.0522 0.075 Uiso 1 1 calc R . .
N1 N 0.2594(4) 1.1262(3) 0.2642(3) 0.0348(5) Uani 1 1 d . . .
C5 C 0.4394(5) 1.1343(4) 0.3038(4) 0.0410(7) Uani 1 1 d . . .
C1 C 0.2534(5) 1.2043(4) 0.3984(4) 0.0408(7) Uani 1 1 d . . .
C4 C 0.6192(5) 1.2260(6) 0.4785(5) 0.0539(9) Uani 1 1 d . . .
H4 H 0.7432 1.2334 0.5038 0.065 Uiso 1 1 calc R . .
C2 C 0.4300(6) 1.2949(5) 0.5752(5) 0.0527(8) Uani 1 1 d . . .
H2 H 0.4243 1.3477 0.6666 0.063 Uiso 1 1 calc R . .
C3 C 0.6144(6) 1.3065(6) 0.6150(5) 0.0591(10) Uani 1 1 d . . .
H3 H 0.7349 1.3682 0.7331 0.071 Uiso 1 1 calc R . .
O1 O -0.0526(4) 0.7501(3) 0.0349(3) 0.0456(5) Uani 1 1 d . . .
C8 C -0.1615(5) 0.6766(5) 0.1056(5) 0.0475(8) Uani 1 1 d . . .
O2 O -0.2318(6) 0.7477(4) 0.1587(5) 0.0752(9) Uani 1 1 d . . .
C9 C -0.2054(6) 0.4866(5) 0.1200(6) 0.0601(10) Uani 1 1 d . . .
H9A H -0.1691 0.4813 0.2438 0.090 Uiso 1 1 calc R . .
H9B H -0.1229 0.4578 0.0907 0.090 Uiso 1 1 calc R . .
H9C H -0.3521 0.3999 0.0345 0.090 Uiso 1 1 calc R . .
C6 C 0.0517(6) 1.1919(5) 0.3506(5) 0.0515(8) Uani 1 1 d . . .
H6A H 0.0117 1.2495 0.2540 0.077 Uiso 1 1 calc R . .
H6B H 0.0704 1.2528 0.4581 0.077 Uiso 1 1 calc R . .
H6C H -0.0566 1.0656 0.3089 0.077 Uiso 1 1 calc R . .
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'
Pd Pd -0.9988 1.0072 '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
O1 Pd1 O1 180.0 2_575 . ?
O1 Pd1 N1 88.68(9) 2_575 . ?
O1 Pd1 N1 91.32(9) . . ?
O1 Pd1 N1 91.32(9) 2_575 2_575 ?
O1 Pd1 N1 88.68(9) . 2_575 ?
N1 Pd1 N1 180.0 . 2_575 ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 N1 C1 119.8(3) . . ?
C5 N1 Pd1 119.5(2) . . ?
C1 N1 Pd1 120.7(2) . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 C7 118.1(3) . . ?
C4 C5 C7 121.3(3) . . ?
N1 C1 C2 120.9(3) . . ?
N1 C1 C6 118.6(3) . . ?
C2 C1 C6 120.6(3) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C8 O1 Pd1 117.5(2) . . ?
O2 C8 O1 124.9(3) . . ?
O2 C8 C9 119.6(3) . . ?
O1 C8 C9 115.5(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
Pd1 O1 2.022(2) 2_575 ?
Pd1 O1 2.022(2) . ?
Pd1 N1 2.048(2) . ?
Pd1 N1 2.048(2) 2_575 ?
C7 C5 1.493(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N1 C5 1.353(4) . ?
N1 C1 1.356(4) . ?
C5 C4 1.380(5) . ?
C1 C2 1.381(5) . ?
C1 C6 1.495(5) . ?
C4 C3 1.375(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
O1 C8 1.271(4) . ?
C8 O2 1.223(5) . ?
C8 C9 1.507(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
