#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:36:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178787 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/41/4104175.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_4104175
loop_
_publ_author_name
'Yang-Hui Zhang'
'Bing-Feng Shi'
'Jin-Quan Yu'
_publ_section_title
;
 Pd(II)-Catalyzed Olefination of Electron-Deficient Arenes Using
 2,6-Dialkylpyridine Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5072
_journal_page_last               5074
_journal_paper_doi               10.1021/ja900327e
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C46 H80 N2 O4 Pd'
_chemical_formula_weight         831.52
_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                98.689(2)
_cell_angle_beta                 101.268(2)
_cell_angle_gamma                101.819(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2776(2)
_cell_length_b                   10.3304(3)
_cell_length_c                   12.6608(3)
_cell_measurement_reflns_used    7093
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      4.46
_cell_volume                     1141.50(5)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.873
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9273
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         4.46
_exptl_absorpt_coefficient_mu    3.587
_exptl_absorpt_correction_T_max  0.556
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.714
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1003P)²+2.0026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1642
_reflns_number_gt                3454
_reflns_number_total             3546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900327e_si_001.cif
_cod_data_source_block           yu11
_cod_original_cell_volume        1141.49(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4104175
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
Pd1 Pd 0.5000 0.5000 0.0000 0.0284(2) Uani 1 2 d S
O1 O 0.4574(4) 0.4143(3) 0.1264(3) 0.0310(8) Uani 1 1 d .
O2 O 0.2809(4) 0.5259(4) 0.1518(3) 0.0438(10) Uani 1 1 d .
N1 N 0.7067(4) 0.6136(4) 0.0951(3) 0.0269(9) Uani 1 1 d .
C1 C 0.8279(6) 0.5599(5) 0.1102(4) 0.0312(11) Uani 1 1 d .
C2 C 0.9728(6) 0.6436(6) 0.1555(5) 0.0395(13) Uani 1 1 d .
H2A H 1.0586 0.6059 0.1649 0.047 Uiso 1 1 calc R
C3 C 0.9911(6) 0.7800(6) 0.1862(6) 0.0472(15) Uani 1 1 d .
H3 H 1.0891 0.8378 0.2168 0.057 Uiso 1 1 calc R
C4 C 0.8651(7) 0.8314(6) 0.1721(6) 0.0478(15) Uani 1 1 d .
H4 H 0.8755 0.9257 0.1933 0.057 Uiso 1 1 calc R
C5 C 0.7236(6) 0.7471(5) 0.1272(5) 0.0340(12) Uani 1 1 d .
C6 C 0.5850(7) 0.8019(6) 0.1214(5) 0.0451(14) Uani 1 1 d .
H6A H 0.5921 0.8720 0.0761 0.054 Uiso 1 1 calc R
H6B H 0.4956 0.7280 0.0828 0.054 Uiso 1 1 calc R
C7 C 0.5587(9) 0.8599(13) 0.2260(7) 0.094(3) Uani 1 1 d D
H7A H 0.6331 0.9497 0.2444 0.112 Uiso 1 1 calc R
C8 C 0.4096(10) 0.9020(12) 0.2154(9) 0.093(3) Uani 1 1 d .
H8A H 0.3264 0.8240 0.1740 0.111 Uiso 1 1 calc R
H8B H 0.3922 0.9262 0.2897 0.111 Uiso 1 1 calc R
C9 C 0.4037(9) 1.0154(8) 0.1605(10) 0.089(3) Uani 1 1 d .
H9A H 0.4833 1.0943 0.2024 0.134 Uiso 1 1 calc R
H9B H 0.3045 1.0362 0.1558 0.134 Uiso 1 1 calc R
H9C H 0.4193 0.9920 0.0863 0.134 Uiso 1 1 calc R
C14 C 0.8083(7) 0.4104(5) 0.0844(5) 0.0386(12) Uani 1 1 d .
H14A H 0.8656 0.3886 0.0286 0.046 Uiso 1 1 calc R
H14B H 0.6999 0.3672 0.0516 0.046 Uiso 1 1 calc R
C15 C 0.8609(8) 0.3493(6) 0.1840(5) 0.0468(15) Uani 1 1 d .
H15 H 0.9708 0.3939 0.2142 0.056 Uiso 1 1 calc R
C16 C 0.8506(9) 0.1995(6) 0.1478(6) 0.0577(18) Uani 1 1 d .
H16A H 0.8706 0.1599 0.2141 0.069 Uiso 1 1 calc R
H16B H 0.7460 0.1547 0.1058 0.069 Uiso 1 1 calc R
C17 C 0.9570(10) 0.1700(7) 0.0794(8) 0.069(2) Uani 1 1 d .
H17A H 0.9264 0.1934 0.0075 0.104 Uiso 1 1 calc R
H17B H 0.9553 0.0737 0.0694 0.104 Uiso 1 1 calc R
H17C H 1.0597 0.2232 0.1160 0.104 Uiso 1 1 calc R
C18 C 0.7821(7) 0.3777(6) 0.2764(5) 0.0429(13) Uani 1 1 d .
H18A H 0.7940 0.4765 0.2951 0.051 Uiso 1 1 calc R
H18B H 0.6725 0.3361 0.2476 0.051 Uiso 1 1 calc R
C19 C 0.8313(8) 0.3317(6) 0.3785(6) 0.0508(16) Uani 1 1 d .
H19A H 0.9427 0.3653 0.4035 0.061 Uiso 1 1 calc R
H19B H 0.8088 0.2319 0.3616 0.061 Uiso 1 1 calc R
C20 C 0.7618(9) 0.3741(7) 0.4731(5) 0.0529(16) Uani 1 1 d .
H20A H 0.7841 0.4739 0.4901 0.063 Uiso 1 1 calc R
H20B H 0.6505 0.3401 0.4484 0.063 Uiso 1 1 calc R
C21 C 0.8132(10) 0.3273(8) 0.5751(6) 0.0644(19) Uani 1 1 d .
H21A H 0.7894 0.2285 0.5602 0.097 Uiso 1 1 calc R
H21B H 0.7614 0.3594 0.6306 0.097 Uiso 1 1 calc R
H21C H 0.9228 0.3630 0.6023 0.097 Uiso 1 1 calc R
C22 C 0.3585(6) 0.4489(5) 0.1780(4) 0.0325(11) Uani 1 1 d .
C23 C 0.3504(7) 0.3850(6) 0.2767(5) 0.0440(14) Uani 1 1 d .
H23A H 0.4373 0.4322 0.3373 0.066 Uiso 1 1 calc R
H23B H 0.3524 0.2899 0.2579 0.066 Uiso 1 1 calc R
H23C H 0.2563 0.3913 0.2990 0.066 Uiso 1 1 calc R
C10 C 0.6016(13) 0.8065(16) 0.3257(7) 0.149(7) Uani 1 1 d D
H10A H 0.6989 0.7824 0.3227 0.178 Uiso 1 1 calc R
H10B H 0.5258 0.7203 0.3162 0.178 Uiso 1 1 calc R
C13 C 0.8531(17) 0.837(2) 0.5344(18) 0.187(9) Uani 1 1 d D
H13A H 0.9271 0.8524 0.6046 0.281 Uiso 1 1 calc R
H13B H 0.9001 0.8830 0.4830 0.281 Uiso 1 1 calc R
H13C H 0.8191 0.7398 0.5038 0.281 Uiso 1 1 calc R
C11 C 0.621(2) 0.877(2) 0.4401(10) 0.162(7) Uani 1 1 d D
H11A H 0.5180 0.8482 0.4528 0.194 Uiso 1 1 calc R
H11B H 0.6311 0.9721 0.4324 0.194 Uiso 1 1 calc R
C12 C 0.721(2) 0.891(3) 0.5524(15) 0.296(19) Uani 1 1 d D
H12A H 0.7546 0.9864 0.5905 0.355 Uiso 1 1 calc R
H12B H 0.6654 0.8383 0.5977 0.355 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 '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
O1 Pd1 O1 180.0 . 2_665
O1 Pd1 N1 89.20(15) . 2_665
O1 Pd1 N1 90.80(15) 2_665 2_665
O1 Pd1 N1 90.80(15) . .
O1 Pd1 N1 89.20(15) 2_665 .
N1 Pd1 N1 179.999(2) 2_665 .
C22 O1 Pd1 119.7(3) . .
C5 N1 C1 120.2(4) . .
C5 N1 Pd1 118.4(3) . .
C1 N1 Pd1 120.6(3) . .
N1 C1 C2 120.0(5) . .
N1 C1 C14 120.5(5) . .
C2 C1 C14 119.4(5) . .
C3 C2 C1 120.0(5) . .
C2 C3 C4 118.6(5) . .
C3 C4 C5 120.3(5) . .
N1 C5 C4 120.7(5) . .
N1 C5 C6 119.0(5) . .
C4 C5 C6 120.1(5) . .
C7 C6 C5 116.2(5) . .
C6 C7 C10 121.6(8) . .
C6 C7 C8 113.7(7) . .
C10 C7 C8 113.6(7) . .
C9 C8 C7 113.9(8) . .
C1 C14 C15 114.3(5) . .
C18 C15 C16 112.7(5) . .
C18 C15 C14 113.6(5) . .
C16 C15 C14 110.4(5) . .
C17 C16 C15 114.3(5) . .
C19 C18 C15 118.1(5) . .
C18 C19 C20 116.7(5) . .
C21 C20 C19 115.9(6) . .
O2 C22 O1 124.7(5) . .
O2 C22 C23 122.4(5) . .
O1 C22 C23 112.9(4) . .
C7 C10 C11 126.2(14) . .
C10 C11 C12 139.0(17) . .
C13 C12 C11 106.3(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 O1 2.008(3) .
Pd1 O1 2.008(3) 2_665
Pd1 N1 2.062(4) 2_665
Pd1 N1 2.062(4) .
O1 C22 1.301(6) .
O2 C22 1.217(6) .
N1 C5 1.345(7) .
N1 C1 1.346(6) .
C1 C2 1.399(8) .
C1 C14 1.495(7) .
C2 C3 1.370(9) .
C3 C4 1.372(9) .
C4 C5 1.376(8) .
C5 C6 1.501(7) .
C6 C7 1.456(10) .
C7 C10 1.469(9) .
C7 C8 1.521(9) .
C8 C9 1.454(14) .
C14 C15 1.533(8) .
C15 C18 1.519(8) .
C15 C16 1.524(8) .
C16 C17 1.482(9) .
C18 C19 1.466(9) .
C19 C20 1.517(9) .
C20 C21 1.474(10) .
C22 C23 1.506(7) .
C10 C11 1.479(9) .
C13 C12 1.488(10) .
C11 C12 1.508(10) .
