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#$Date: 2016-03-21 13:15:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178695 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/06/4080633.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_4080633
loop_
_publ_author_name
'De Crisci, Antonio G.'
'Chung, Kevin'
'Oliver, Allen G.'
'Solis-Ibarra, Diego'
'Waymouth, Robert M.'
_publ_section_title
;
 Chemoselective Oxidation of Polyols with Chiral Palladium Catalysts
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              2257
_journal_paper_doi               10.1021/om4001549
_journal_volume                  32
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H14 Cl2 N2 O Pd, C H Cl3'
_chemical_formula_sum            'C16 H15 Cl5 N2 O Pd'
_chemical_formula_weight         534.95
_chemical_name_common            ACD-2
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7515(7)
_cell_length_b                   11.4741(8)
_cell_length_c                   17.4586(14)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.7161
_cell_measurement_theta_min      2.3331
_cell_volume                     1953.4(3)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker Instrument Service v3.0.25'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45035
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.214
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0148
_refine_ls_R_factor_gt           0.0142
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0179P)²+0.6579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0340
_refine_ls_wR_factor_ref         0.0342
_reflns_number_gt                3510
_reflns_number_total             3577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4001549_si_002.cif
_cod_data_source_block           4c
_cod_database_code               4080633
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Pd Pd1 0.339368(14) 0.41472(12) 0.009302(8) 0.01083(4) Uani d . 1
Cl Cl1 0.53346(5) 0.46920(4) 0.07265(3) 0.01718(11) Uani d . 1
Cl Cl2 0.47916(5) 0.35591(5) -0.09006(3) 0.01835(11) Uani d . 1
Cl Cl3 1.04164(6) 0.31289(6) 0.41073(4) 0.03504(15) Uani d . 1
Cl Cl5 0.82400(6) 0.40075(5) 0.31488(3) 0.02880(12) Uani d . 1
Cl Cl4 0.75890(7) 0.28074(5) 0.45589(3) 0.02969(14) Uani d . 1
C C16 0.2487(2) 0.51147(17) 0.17641(12) 0.0149(4) Uani d . 1
H H16 0.3198 0.5743 0.1777 0.018 Uiso calc R 1
O O1 0.01311(15) 0.51642(13) 0.13746(8) 0.0186(3) Uani d . 1
N N2 0.13941(17) 0.38209(13) -0.03504(9) 0.0131(4) Uani d . 1
C C18 -0.0969(2) 0.42645(16) -0.00324(12) 0.0184(4) Uani d . 1
H H18 -0.1605 0.4611 0.0311 0.022 Uiso calc R 1
N N1 0.22435(17) 0.47195(14) 0.09657(10) 0.0133(4) Uani d . 1
C C2 0.2904(2) 0.41026(19) 0.22730(10) 0.0161(4) Uani d . 1
C C3 0.2121(2) 0.30955(19) 0.22892(13) 0.0213(5) Uani d . 1
H H3 0.1342 0.302 0.1967 0.026 Uiso calc R 1
C C4 0.2492(3) 0.2189(2) 0.27863(15) 0.0322(6) Uani d . 1
H H4 0.1966 0.1492 0.2798 0.039 Uiso calc R 1
C C5 0.3619(3) 0.2307(2) 0.32584(15) 0.0394(7) Uani d . 1
H H5 0.3865 0.1693 0.3596 0.047 Uiso calc R 1
C C6 0.4390(3) 0.3313(3) 0.32406(14) 0.0391(7) Uani d . 1
H H6 0.5159 0.3394 0.3571 0.047 Uiso calc R 1
C C7 0.4048(2) 0.4205(2) 0.27434(12) 0.0257(5) Uani d . 1
H H7 0.4595 0.4889 0.2723 0.031 Uiso calc R 1
C C8 0.1054(2) 0.56140(18) 0.19751(12) 0.0175(5) Uani d . 1
H H8A 0.0762 0.534 0.2488 0.021 Uiso calc R 1
H H8B 0.1068 0.6477 0.1973 0.021 Uiso calc R 1
C C9 0.0956(2) 0.47473(17) 0.08320(12) 0.0143(4) Uani d . 1
C C10 0.0403(2) 0.42826(16) 0.01178(11) 0.0146(4) Uani d . 1
C C11 0.0962(2) 0.32880(17) -0.09952(12) 0.0162(4) Uani d . 1
C C12 0.1951(2) 0.2733(2) -0.15320(12) 0.0225(5) Uani d . 1
H H12A 0.2517 0.3335 -0.1773 0.034 Uiso calc R 1
H H12B 0.1447 0.2305 -0.1928 0.034 Uiso calc R 1
H H12C 0.2541 0.2192 -0.1248 0.034 Uiso calc R 1
C C13 -0.0436(2) 0.32403(18) -0.11697(12) 0.0187(5) Uani d . 1
H H13 -0.0719 0.286 -0.1627 0.022 Uiso calc R 1
C C14 -0.1414(2) 0.37238(17) -0.07027(13) 0.0196(5) Uani d . 1
H H14 -0.236 0.3691 -0.0831 0.024 Uiso calc R 1
C C15 0.8771(2) 0.37425(18) 0.41025(12) 0.0195(5) Uani d . 1
H H15 0.8798 0.45 0.4385 0.023 Uiso calc R 1
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'
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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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
N1 Pd1 N2 79.72(6)
N1 Pd1 Cl1 90.35(5)
N2 Pd1 Cl1 169.78(5)
N1 Pd1 Cl2 177.27(5)
N2 Pd1 Cl2 102.48(5)
Cl1 Pd1 Cl2 87.39(2)
N1 C16 C2 111.02(16)
N1 C16 C8 101.05(16)
C2 C16 C8 112.59(17)
N1 C16 H16 110.6
C2 C16 H16 110.6
C8 C16 H16 110.6
C9 O1 C8 105.22(16)
C11 N2 C10 116.87(17)
C11 N2 Pd1 131.98(14)
C10 N2 Pd1 111.12(12)
C10 C18 C14 118.27(19)
C10 C18 H18 120.9
C14 C18 H18 120.9
C9 N1 C16 108.72(18)
C9 N1 Pd1 114.81(15)
C3 C2 C7 120.0(2)
C3 C2 C16 120.18(18)
C7 C2 C16 119.7(2)
C2 C3 C4 119.3(2)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 120.1(2)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 120.2(2)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 120.2(2)
C5 C6 H6 119.9
C7 C6 H6 119.9
C6 C7 C2 120.1(3)
C6 C7 H7 119.9
C2 C7 H7 119.9
O1 C8 C16 104.54(15)
O1 C8 H8A 110.8
C16 C8 H8A 110.8
O1 C8 H8B 110.8
C16 C8 H8B 110.8
H8A C8 H8B 108.9
N1 C9 O1 118.2(2)
N1 C9 C10 120.69(19)
O1 C9 C10 121.03(18)
C18 C10 N2 124.81(19)
C18 C10 C9 122.19(19)
N2 C10 C9 112.91(17)
N2 C11 C13 120.29(19)
N2 C11 C12 121.13(18)
C13 C11 C12 118.6(2)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 C11 122.2(2)
C14 C13 H13 118.9
C11 C13 H13 118.9
C13 C14 C18 117.6(2)
C13 C14 H14 121.2
C18 C14 H14 121.2
Cl3 C15 Cl4 110.59(12)
Cl3 C15 Cl5 109.97(12)
Cl4 C15 Cl5 109.75(12)
Cl3 C15 H15 108.8
Cl4 C15 H15 108.8
Cl5 C15 H15 108.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 N1 2.0026(17)
Pd1 N2 2.1311(17)
Pd1 Cl1 2.2795(5)
Pd1 Cl2 2.3071(5)
Cl3 C15 1.752(2)
Cl5 C15 1.770(2)
Cl4 C15 1.765(2)
C16 N1 1.485(3)
C16 C2 1.518(3)
C16 C8 1.554(3)
C16 H16 1.0
O1 C9 1.332(2)
O1 C8 1.475(2)
N2 C11 1.349(3)
N2 C10 1.372(3)
C18 C10 1.363(3)
C18 C14 1.394(3)
C18 H18 0.95
N1 C9 1.277(3)
C2 C3 1.385(3)
C2 C7 1.390(3)
C3 C4 1.402(3)
C3 H3 0.95
C4 C5 1.381(4)
C4 H4 0.95
C5 C6 1.378(4)
C5 H5 0.95
C6 C7 1.383(4)
C6 H6 0.95
C7 H7 0.95
C8 H8A 0.99
C8 H8B 0.99
C9 C10 1.460(3)
C11 C13 1.398(3)
C11 C12 1.488(3)
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
C13 C14 1.372(3)
C13 H13 0.95
C14 H14 0.95
C15 H15 1.0
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 Pd1 N2 C11 -174.45(18)
Cl1 Pd1 N2 C11 171.87(17)
Cl2 Pd1 N2 C11 7.21(18)
N1 Pd1 N2 C10 7.52(12)
Cl1 Pd1 N2 C10 -6.2(3)
Cl2 Pd1 N2 C10 -170.82(11)
C2 C16 N1 C9 108.1(2)
C8 C16 N1 C9 -11.5(2)
C2 C16 N1 Pd1 -70.4(2)
C8 C16 N1 Pd1 169.97(15)
N2 Pd1 N1 C9 -7.05(15)
Cl1 Pd1 N1 C9 170.55(15)
N2 Pd1 N1 C16 171.38(19)
Cl1 Pd1 N1 C16 -11.03(18)
N1 C16 C2 C3 -51.4(2)
C8 C16 C2 C3 61.1(2)
N1 C16 C2 C7 130.90(19)
C8 C16 C2 C7 -116.6(2)
C7 C2 C3 C4 0.3(3)
C16 C2 C3 C4 -177.40(19)
C2 C3 C4 C5 0.5(3)
C3 C4 C5 C6 -0.3(4)
C4 C5 C6 C7 -0.7(4)
C5 C6 C7 C2 1.6(4)
C3 C2 C7 C6 -1.4(3)
C16 C2 C7 C6 176.3(2)
C9 O1 C8 C16 -13.0(2)
N1 C16 C8 O1 14.54(19)
C2 C16 C8 O1 -103.95(18)
C16 N1 C9 O1 3.9(3)
Pd1 N1 C9 O1 -177.25(13)
C16 N1 C9 C10 -173.24(17)
Pd1 N1 C9 C10 5.6(2)
C8 O1 C9 N1 6.4(2)
C8 O1 C9 C10 -176.53(17)
C14 C18 C10 N2 1.1(3)
C14 C18 C10 C9 -175.15(18)
C11 N2 C10 C18 -1.7(3)
Pd1 N2 C10 C18 176.66(15)
C11 N2 C10 C9 174.85(16)
Pd1 N2 C10 C9 -6.79(19)
N1 C9 C10 C18 177.8(2)
O1 C9 C10 C18 0.8(3)
N1 C9 C10 N2 1.2(3)
O1 C9 C10 N2 -175.85(17)
C10 N2 C11 C13 1.1(3)
Pd1 N2 C11 C13 -176.84(14)
C10 N2 C11 C12 -178.45(18)
Pd1 N2 C11 C12 3.6(3)
N2 C11 C13 C14 0.0(3)
C12 C11 C13 C14 179.57(19)
C11 C13 C14 C18 -0.6(3)
C10 C18 C14 C13 0.1(3)
