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#$Date: 2016-03-25 13:45:44 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179862 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/58/7015800.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_7015800
loop_
_publ_author_name
'Chotima, Ratanon'
'Dale, Tim'
'Green, Michael'
'Hey, Thomas W.'
'McMullin, Claire L.'
'Nunns, Adam'
'Guy Orpen, A.'
'Shishkov, Igor V.'
'Wass, Duncan F.'
'Wingad, Richard L.'
_publ_section_title
;
 Cyclopropenylidene carbene ligands in palladium catalysed coupling
 reactions: carbene ligand rotation and application to the Stille
 reaction.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5316
_journal_page_last               5323
_journal_paper_doi               10.1039/c1dt10109a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C17 H11 Cl2 F2 N Pd'
_chemical_formula_sum            'C17 H11 Cl2 F2 N Pd'
_chemical_formula_weight         444.57
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.697(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0238(8)
_cell_length_b                   7.3625(4)
_cell_length_c                   17.0969(9)
_cell_measurement_reflns_used    22924
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1637.57(16)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on κ-goniostat
;
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1310
_diffrn_reflns_av_sigmaI/netI    0.1259
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15754
_diffrn_reflns_theta_full        27.71
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0891
_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)+(0.0000P)²+16.7812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                2388
_reflns_number_total             3755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10109a.txt
_cod_data_source_block           12
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7015800
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.76232(5) 0.86502(10) 0.15582(4) 0.02093(19) Uani 1 1 d . . .
Cl1 Cl 0.61490(18) 0.9550(3) 0.21415(12) 0.0284(5) Uani 1 1 d . . .
Cl2 Cl 0.90481(18) 0.7875(4) 0.08900(13) 0.0321(6) Uani 1 1 d . . .
F1 F 0.1945(4) 0.5402(8) 0.0281(3) 0.0341(13) Uani 1 1 d . . .
F2 F 0.8199(4) 1.1782(8) -0.2873(3) 0.0353(14) Uani 1 1 d . . .
N1 N 0.8511(5) 0.8720(11) 0.2606(4) 0.0240(16) Uani 1 1 d . . .
C1 C 0.6827(7) 0.8482(12) 0.0587(5) 0.0206(19) Uani 1 1 d . . .
C2 C 0.5906(6) 0.7990(11) 0.0197(5) 0.0164(18) Uani 1 1 d . . .
C3 C 0.6700(6) 0.8761(11) -0.0202(5) 0.0179(17) Uani 1 1 d . . .
C4 C 0.4884(6) 0.7281(11) 0.0207(5) 0.0176(18) Uani 1 1 d . . .
C5 C 0.4542(6) 0.6600(11) 0.0907(4) 0.0161(18) Uani 1 1 d . . .
H5 H 0.4984 0.6598 0.1365 0.019 Uiso 1 1 calc R . .
C6 C 0.3541(7) 0.5917(12) 0.0932(5) 0.024(2) Uani 1 1 d . . .
H6 H 0.3294 0.5412 0.1398 0.029 Uiso 1 1 calc R . .
C7 C 0.2929(7) 0.6006(11) 0.0254(5) 0.022(2) Uani 1 1 d . . .
C8 C 0.3245(7) 0.6660(12) -0.0446(5) 0.021(2) Uani 1 1 d . . .
H8 H 0.2795 0.6670 -0.0900 0.026 Uiso 1 1 calc R . .
C9 C 0.4225(7) 0.7294(12) -0.0469(5) 0.0219(19) Uani 1 1 d . . .
H9 H 0.4466 0.7751 -0.0947 0.026 Uiso 1 1 calc R . .
C10 C 0.7110(7) 0.9465(12) -0.0908(5) 0.0210(19) Uani 1 1 d . . .
C11 C 0.6504(7) 0.9475(12) -0.1616(5) 0.0214(19) Uani 1 1 d . . .
H11 H 0.5840 0.8937 -0.1636 0.026 Uiso 1 1 calc R . .
C12 C 0.6876(7) 1.0263(12) -0.2278(5) 0.022(2) Uani 1 1 d . . .
H12 H 0.6476 1.0278 -0.2757 0.027 Uiso 1 1 calc R . .
C13 C 0.7836(7) 1.1022(12) -0.2224(5) 0.024(2) Uani 1 1 d . . .
C14 C 0.8450(6) 1.1031(12) -0.1545(5) 0.022(2) Uani 1 1 d . . .
H14 H 0.9114 1.1567 -0.1536 0.026 Uiso 1 1 calc R . .
C15 C 0.8081(7) 1.0242(13) -0.0874(5) 0.025(2) Uani 1 1 d . . .
H15 H 0.8489 1.0236 -0.0399 0.031 Uiso 1 1 calc R . .
C16 C 0.9068(6) 0.8557(13) 0.3142(5) 0.0233(19) Uani 1 1 d . . .
C17 C 0.9775(7) 0.8312(13) 0.3825(5) 0.027(2) Uani 1 1 d . . .
H17A H 0.9381 0.8194 0.4297 0.040 Uiso 1 1 calc R . .
H17B H 1.0233 0.9365 0.3878 0.040 Uiso 1 1 calc R . .
H17C H 1.0184 0.7211 0.3757 0.040 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'
F F 0.0171 0.0103 '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'
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
C1 Pd1 N1 177.5(3) . . ?
C1 Pd1 Cl2 88.3(3) . . ?
N1 Pd1 Cl2 90.3(2) . . ?
C1 Pd1 Cl1 88.0(3) . . ?
N1 Pd1 Cl1 93.5(2) . . ?
Cl2 Pd1 Cl1 175.49(9) . . ?
C16 N1 Pd1 170.6(8) . . ?
C3 C1 C2 60.3(6) . . ?
C3 C1 Pd1 151.6(7) . . ?
C2 C1 Pd1 148.1(7) . . ?
C3 C2 C1 59.0(6) . . ?
C3 C2 C4 150.6(8) . . ?
C1 C2 C4 150.4(8) . . ?
C1 C3 C2 60.7(6) . . ?
C1 C3 C10 148.1(8) . . ?
C2 C3 C10 151.1(8) . . ?
C5 C4 C9 120.1(8) . . ?
C5 C4 C2 118.6(7) . . ?
C9 C4 C2 121.3(8) . . ?
C4 C5 C6 119.5(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 117.4(8) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
F1 C7 C8 117.8(8) . . ?
F1 C7 C6 117.8(8) . . ?
C8 C7 C6 124.4(8) . . ?
C9 C8 C7 117.8(8) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C8 C9 C4 120.7(8) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C15 C10 C11 120.3(8) . . ?
C15 C10 C3 119.2(8) . . ?
C11 C10 C3 120.4(8) . . ?
C12 C11 C10 120.1(8) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 118.1(8) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
F2 C13 C12 118.0(7) . . ?
F2 C13 C14 118.6(8) . . ?
C12 C13 C14 123.4(8) . . ?
C13 C14 C15 118.9(8) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 119.1(8) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N1 C16 C17 178.9(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C1 1.920(8) . ?
Pd1 N1 2.087(7) . ?
Pd1 Cl2 2.297(2) . ?
Pd1 Cl1 2.302(2) . ?
F1 C7 1.360(9) . ?
F2 C13 1.348(9) . ?
N1 C16 1.148(10) . ?
C1 C3 1.368(11) . ?
C1 C2 1.393(11) . ?
C2 C3 1.387(12) . ?
C2 C4 1.431(11) . ?
C3 C10 1.439(12) . ?
C4 C5 1.390(11) . ?
C4 C9 1.408(11) . ?
C5 C6 1.399(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.371(12) . ?
C8 C9 1.361(12) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.387(13) . ?
C10 C11 1.413(11) . ?
C11 C12 1.379(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(11) . ?
C14 C15 1.392(12) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.463(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl2 Pd1 C1 C3 -40.1(14) . . . . ?
Cl1 Pd1 C1 C3 137.3(14) . . . . ?
Cl2 Pd1 C1 C2 142.7(13) . . . . ?
Cl1 Pd1 C1 C2 -39.9(12) . . . . ?
Pd1 C1 C2 C3 178.4(14) . . . . ?
C3 C1 C2 C4 -177.4(17) . . . . ?
Pd1 C1 C2 C4 1(3) . . . . ?
Pd1 C1 C3 C2 -178.3(15) . . . . ?
C2 C1 C3 C10 176.4(16) . . . . ?
Pd1 C1 C3 C10 -2(3) . . . . ?
C4 C2 C3 C1 177.4(17) . . . . ?
C1 C2 C3 C10 -176.1(17) . . . . ?
C4 C2 C3 C10 1(3) . . . . ?
C3 C2 C4 C5 178.4(13) . . . . ?
C1 C2 C4 C5 -6(2) . . . . ?
C3 C2 C4 C9 -3(2) . . . . ?
C1 C2 C4 C9 172.8(13) . . . . ?
C9 C4 C5 C6 0.5(12) . . . . ?
C2 C4 C5 C6 179.4(8) . . . . ?
C4 C5 C6 C7 -1.8(12) . . . . ?
C5 C6 C7 F1 -177.8(7) . . . . ?
C5 C6 C7 C8 2.3(14) . . . . ?
F1 C7 C8 C9 178.8(8) . . . . ?
C6 C7 C8 C9 -1.2(14) . . . . ?
C7 C8 C9 C4 -0.3(13) . . . . ?
C5 C4 C9 C8 0.6(13) . . . . ?
C2 C4 C9 C8 -178.3(8) . . . . ?
C1 C3 C10 C15 2(2) . . . . ?
C2 C3 C10 C15 175.1(14) . . . . ?
C1 C3 C10 C11 -174.3(12) . . . . ?
C2 C3 C10 C11 -1(2) . . . . ?
C15 C10 C11 C12 -0.2(13) . . . . ?
C3 C10 C11 C12 175.6(8) . . . . ?
C10 C11 C12 C13 0.0(13) . . . . ?
C11 C12 C13 F2 179.6(8) . . . . ?
C11 C12 C13 C14 0.3(14) . . . . ?
F2 C13 C14 C15 -179.7(8) . . . . ?
C12 C13 C14 C15 -0.4(14) . . . . ?
C11 C10 C15 C14 0.1(13) . . . . ?
C3 C10 C15 C14 -175.8(8) . . . . ?
C13 C14 C15 C10 0.2(13) . . . . ?
