#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/07/7000783.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_7000783
loop_
_publ_author_name
'Lasri, Jamal'
'da Silva, M. Fátima C. Guedes'
'Kopylovich, Maximilian N.'
'Mukhopadhyay, Suman'
'Charmier, M. Adília Januário'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 PdII-promoted [2 + 3] cycloaddition of pyrroline N-oxide to
 organonitriles. Application of (Δ4-1,2,4-oxadiazoline)-PdII complexes
 in the Suzuki--Miyaura reaction
;
_journal_issue                   12
_journal_name_full               'Dalton Transactions'
_journal_page_first              2210
_journal_page_last               2216
_journal_paper_doi               10.1039/b813996b
_journal_year                    2009
_chemical_formula_moiety         'C26 H30 Cl2 F2 N4 O2 Pd'
_chemical_formula_sum            'C26 H30 Cl2 F2 N4 O2 Pd'
_chemical_formula_weight         645.84
_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                105.666(11)
_cell_angle_beta                 105.464(12)
_cell_angle_gamma                102.764(10)
_cell_formula_units_Z            1
_cell_length_a                   7.3090(14)
_cell_length_b                   9.4080(18)
_cell_length_c                   10.818(2)
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.55
_cell_volume                     655.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1167
_diffrn_reflns_av_sigmaI/netI    0.0878
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7226
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.8936
_exptl_absorpt_correction_T_min  0.7490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.085
_refine_diff_density_min         -1.657
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0356
_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)+(0.0200P)²+0.1455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                2073
_reflns_number_total             2308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813996b.txt
_cod_data_source_block           jl216b
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7000783
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
C1 C 0.6844(4) 0.1681(3) 0.9021(3) 0.0197(6) Uani 1 1 d . . .
C2 C 0.8069(5) 0.0566(3) 0.8951(4) 0.0316(8) Uani 1 1 d . . .
H2A H 0.8113 0.0195 0.8025 0.047 Uiso 1 1 calc R . .
H2B H 0.7450 -0.0321 0.9174 0.047 Uiso 1 1 calc R . .
H2C H 0.9432 0.1107 0.9608 0.047 Uiso 1 1 calc R . .
C3 C 0.6735(5) 0.2298(3) 1.0432(3) 0.0276(7) Uani 1 1 d . . .
H3A H 0.5933 0.3006 1.0438 0.041 Uiso 1 1 calc R . .
H3B H 0.8088 0.2859 1.1098 0.041 Uiso 1 1 calc R . .
H3C H 0.6114 0.1429 1.0675 0.041 Uiso 1 1 calc R . .
C4 C 0.4787(5) 0.0951(3) 0.7888(3) 0.0224(6) Uani 1 1 d . . .
H4A H 0.3804 0.1426 0.8152 0.027 Uiso 1 1 calc R . .
H4B H 0.4288 -0.0185 0.7678 0.027 Uiso 1 1 calc R . .
C5 C 0.5166(4) 0.1310(3) 0.6662(3) 0.0212(6) Uani 1 1 d . . .
H5A H 0.5560 0.0488 0.6108 0.025 Uiso 1 1 calc R . .
H5B H 0.3983 0.1454 0.6069 0.025 Uiso 1 1 calc R . .
C6 C 0.6853(4) 0.2794(3) 0.7387(3) 0.0171(6) Uani 1 1 d . . .
C7 C 0.6710(5) 0.3682(3) 0.5425(3) 0.0207(6) Uani 1 1 d . . .
C8 C 0.7504(4) 0.5078(3) 0.5076(3) 0.0195(6) Uani 1 1 d . . .
C9 C 0.8655(5) 0.6527(3) 0.6040(3) 0.0264(7) Uani 1 1 d . . .
H9 H 0.8876 0.6701 0.6982 0.032 Uiso 1 1 calc R . .
C10 C 0.9496(5) 0.7735(4) 0.5647(3) 0.0297(7) Uani 1 1 d . . .
H10 H 1.0310 0.8730 0.6301 0.036 Uiso 1 1 calc R . .
C11 C 0.9088(5) 0.7417(4) 0.4258(4) 0.0287(8) Uani 1 1 d . . .
C12 C 0.7885(5) 0.6043(4) 0.3283(3) 0.0297(8) Uani 1 1 d . . .
H12 H 0.7598 0.5899 0.2340 0.036 Uiso 1 1 calc R . .
C13 C 0.7076(5) 0.4846(3) 0.3690(3) 0.0260(7) Uani 1 1 d . . .
H13 H 0.6230 0.3868 0.3023 0.031 Uiso 1 1 calc R . .
N1 N 0.7786(4) 0.3035(2) 0.8645(2) 0.0159(5) Uani 1 1 d . . .
N2 N 0.7400(4) 0.3878(3) 0.6798(2) 0.0210(5) Uani 1 1 d D . .
O1 O 0.5612(4) 0.2458(2) 0.4563(2) 0.0307(5) Uani 1 1 d . . .
Cl1 Cl 1.23377(11) 0.37238(8) 1.02772(7) 0.02533(18) Uani 1 1 d . . .
F1 F 0.9951(3) 0.8581(2) 0.3866(2) 0.0439(6) Uani 1 1 d . . .
Pd1 Pd 1.0000 0.5000 1.0000 0.01405(11) Uani 1 2 d S . .
H2 H 0.7566 0.4784 0.7359 0.017 Uiso 1 1 d 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'
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'
F F 0.0171 0.0103 '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
C3 C1 N1 109.1(2) . . ?
C3 C1 C2 111.7(2) . . ?
N1 C1 C2 109.2(2) . . ?
C3 C1 C4 113.2(2) . . ?
N1 C1 C4 101.8(2) . . ?
C2 C1 C4 111.3(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 C5 103.7(2) . . ?
C1 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C1 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C4 100.1(2) . . ?
C6 C5 H5A 111.7 . . ?
C4 C5 H5A 111.7 . . ?
C6 C5 H5B 111.7 . . ?
C4 C5 H5B 111.7 . . ?
H5A C5 H5B 109.5 . . ?
N1 C6 N2 120.6(3) . . ?
N1 C6 C5 114.9(2) . . ?
N2 C6 C5 124.5(2) . . ?
O1 C7 N2 122.3(2) . . ?
O1 C7 C8 122.4(2) . . ?
N2 C7 C8 115.3(3) . . ?
C9 C8 C13 119.7(2) . . ?
C9 C8 C7 123.9(2) . . ?
C13 C8 C7 116.3(3) . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 116.8(3) . . ?
C11 C10 H10 121.6 . . ?
C9 C10 H10 121.6 . . ?
C12 C11 F1 118.8(3) . . ?
C12 C11 C10 123.9(2) . . ?
F1 C11 C10 117.2(3) . . ?
C11 C12 C13 118.5(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C6 N1 C1 109.2(2) . . ?
C6 N1 Pd1 126.11(17) . . ?
C1 N1 Pd1 124.38(17) . . ?
C7 N2 C6 126.5(2) . . ?
C7 N2 H2 115.7 . . ?
C6 N2 H2 107.8 . . ?
N1 Pd1 N1 180.0 2_767 . ?
N1 Pd1 Cl1 87.00(7) 2_767 . ?
N1 Pd1 Cl1 93.00(7) . . ?
N1 Pd1 Cl1 93.00(7) 2_767 2_767 ?
N1 Pd1 Cl1 87.00(7) . 2_767 ?
Cl1 Pd1 Cl1 180.0 . 2_767 ?
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
C1 C3 1.510(4) . ?
C1 N1 1.518(3) . ?
C1 C2 1.522(4) . ?
C1 C4 1.530(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.532(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.489(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.281(3) . ?
C6 N2 1.382(3) . ?
C7 O1 1.205(4) . ?
C7 N2 1.381(3) . ?
C7 C8 1.501(4) . ?
C8 C9 1.383(4) . ?
C8 C13 1.391(4) . ?
C9 C10 1.393(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.350(5) . ?
C11 F1 1.365(3) . ?
C12 C13 1.387(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 Pd1 2.033(2) . ?
N2 H2 0.864 . ?
Cl1 Pd1 2.2975(8) . ?
Pd1 N1 2.033(2) 2_767 ?
Pd1 Cl1 2.2975(8) 2_767 ?
