#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:13:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178684 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/95/4079586.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_4079586
loop_
_publ_author_name
'Mantas-Öktem, Kevser'
'Öfele, Karl'
'Pöthig, Alexander'
'Bechlars, Bettina'
'Herrmann, Wolfgang A.'
'Kühn, Fritz E.'
_publ_section_title
;
 Reactions of Nitrogen Donors with Cycloheptatrienylidene Complexes: Metal
 Coordination versus Nucleophilic Attack on the Carbene Ligand
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              8249
_journal_paper_doi               10.1021/om300867g
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C28 H30 Br2 N2 Pd2, 2 (F6 P), C3 H6 O'
_chemical_formula_sum            'C31 H36 Br2 F12 N2 O P2 Pd2'
_chemical_formula_weight         1115.18
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 96.834(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   22.8075(9)
_cell_length_b                   7.9164(3)
_cell_length_c                   10.4810(4)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.50
_cell_volume                     1878.93(13)
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'PLATON (Spek, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18526
_diffrn_reflns_theta_full        24.84
_diffrn_reflns_theta_max         24.84
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.258
_exptl_absorpt_correction_T_max  0.7806
_exptl_absorpt_correction_T_min  0.4415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.049(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0192
_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)+(0.0218P)²+0.8014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0487
_reflns_number_gt                3059
_reflns_number_total             3112
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om300867g_si_002.cif
_cod_data_source_block           1b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4079586
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.445303(9) 0.27343(3) 0.06674(2) 0.02118(7) Uani 1 1 d .
Br1 Br 0.544680(13) 0.14083(4) 0.15434(3) 0.02384(9) Uani 1 1 d .
C12 C 0.37985(14) 0.5606(4) -0.2425(3) 0.0250(7) Uani 1 1 d .
H12 H 0.4003 0.4568 -0.2263 0.030 Uiso 1 1 calc R
C11 C 0.35833(14) 0.6025(4) -0.3666(3) 0.0282(8) Uani 1 1 d .
C10 C 0.32942(13) 0.7581(5) -0.3861(3) 0.0295(7) Uani 1 1 d .
H10 H 0.3144 0.7909 -0.4710 0.035 Uiso 1 1 calc R
C9 C 0.32220(14) 0.8648(5) -0.2853(3) 0.0294(8) Uani 1 1 d .
C8 C 0.34390(14) 0.8130(4) -0.1611(3) 0.0259(8) Uani 1 1 d .
H8 H 0.3385 0.8826 -0.0896 0.031 Uiso 1 1 calc R
C1 C 0.39523(13) 0.6125(4) -0.0131(3) 0.0220(7) Uani 1 1 d .
C2 C 0.37142(14) 0.4514(4) 0.0238(3) 0.0247(7) Uani 1 1 d .
H2 H 0.3506 0.3855 -0.0426 0.030 Uiso 1 1 calc R
C3 C 0.37649(14) 0.3848(4) 0.1486(3) 0.0246(7) Uani 1 1 d .
H3 H 0.3444 0.3219 0.1743 0.030 Uiso 1 1 calc R
C4 C 0.42799(14) 0.4077(5) 0.2383(3) 0.0275(7) Uani 1 1 d .
H4 H 0.4392 0.3154 0.2938 0.033 Uiso 1 1 calc R
C5 C 0.46456(15) 0.5547(4) 0.2538(3) 0.0284(8) Uani 1 1 d .
H5 H 0.4928 0.5549 0.3282 0.034 Uiso 1 1 calc R
C6 C 0.46509(14) 0.6935(4) 0.1787(3) 0.0265(7) Uani 1 1 d .
H6 H 0.4896 0.7838 0.2124 0.032 Uiso 1 1 calc R
C7 C 0.43311(13) 0.7201(4) 0.0549(3) 0.0240(7) Uani 1 1 d .
H7 H 0.4391 0.8257 0.0155 0.029 Uiso 1 1 calc R
C13 C 0.2908(2) 1.0315(5) -0.3029(4) 0.0480(11) Uani 1 1 d .
H13A H 0.2901 1.0859 -0.2191 0.072 Uiso 1 1 calc R
H13B H 0.2502 1.0130 -0.3427 0.072 Uiso 1 1 calc R
H13C H 0.3115 1.1044 -0.3584 0.072 Uiso 1 1 calc R
C14 C 0.36535(18) 0.4844(5) -0.4744(3) 0.0392(9) Uani 1 1 d .
H14A H 0.3469 0.5333 -0.5552 0.059 Uiso 1 1 calc R
H14B H 0.3463 0.3765 -0.4591 0.059 Uiso 1 1 calc R
H14C H 0.4075 0.4656 -0.4798 0.059 Uiso 1 1 calc R
N1 N 0.37249(11) 0.6645(3) -0.1429(2) 0.0222(6) Uani 1 1 d .
P1 P 0.20198(4) 0.44386(12) -0.21695(9) 0.02713(19) Uani 1 1 d .
F1 F 0.25694(13) 0.4000(4) -0.2882(4) 0.0795(11) Uani 1 1 d .
F2 F 0.14636(11) 0.4883(3) -0.1452(3) 0.0558(7) Uani 1 1 d .
F3 F 0.18049(13) 0.5787(3) -0.3246(3) 0.0612(7) Uani 1 1 d .
F4 F 0.22291(13) 0.3112(3) -0.1080(3) 0.0661(8) Uani 1 1 d .
F5 F 0.16568(11) 0.2979(3) -0.2943(2) 0.0547(6) Uani 1 1 d .
F6 F 0.23858(12) 0.5898(3) -0.1412(3) 0.0657(8) Uani 1 1 d .
O1 O 0.5000 0.2461(6) 0.5000 0.0436(10) Uani 1 2 d S
C15 C 0.5000 0.0921(8) 0.5000 0.0363(13) Uani 1 2 d S
C16 C 0.55562(18) -0.0034(7) 0.5043(5) 0.0561(12) Uani 1 1 d .
H16A H 0.5872 0.0719 0.4830 0.084 Uiso 1 1 calc R
H16B H 0.5507 -0.0961 0.4419 0.084 Uiso 1 1 calc R
H16C H 0.5660 -0.0497 0.5907 0.084 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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
C3 Pd1 C4 39.26(13) . .
C3 Pd1 C2 38.15(13) . .
C4 Pd1 C2 69.20(12) . .
C3 Pd1 Br1 134.90(9) . .
C4 Pd1 Br1 98.29(9) . .
C2 Pd1 Br1 163.11(9) . .
C3 Pd1 Br1 134.22(10) . 2_655
C4 Pd1 Br1 172.11(9) . 2_655
C2 Pd1 Br1 102.96(9) . 2_655
Br1 Pd1 Br1 89.200(13) . 2_655
C3 Pd1 Pd1 154.83(10) . 2_655
C4 Pd1 Pd1 129.11(9) . 2_655
C2 Pd1 Pd1 124.27(8) . 2_655
Br1 Pd1 Pd1 54.491(9) . 2_655
Br1 Pd1 Pd1 54.116(9) 2_655 2_655
Pd1 Br1 Pd1 71.393(11) . 2_655
N1 C12 C11 121.3(3) . .
N1 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
C12 C11 C10 117.4(3) . .
C12 C11 C14 120.5(3) . .
C10 C11 C14 122.1(3) . .
C9 C10 C11 121.6(3) . .
C9 C10 H10 119.2 . .
C11 C10 H10 119.2 . .
C10 C9 C8 118.2(3) . .
C10 C9 C13 122.9(3) . .
C8 C9 C13 118.9(3) . .
N1 C8 C9 120.0(3) . .
N1 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C7 C1 C2 130.3(3) . .
C7 C1 N1 116.6(3) . .
C2 C1 N1 113.1(3) . .
C3 C2 C1 125.8(3) . .
C3 C2 Pd1 65.95(17) . .
C1 C2 Pd1 108.3(2) . .
C3 C2 H2 117.1 . .
C1 C2 H2 117.1 . .
Pd1 C2 H2 95.9 . .
C2 C3 C4 122.5(3) . .
C2 C3 Pd1 75.90(18) . .
C4 C3 Pd1 73.89(17) . .
C2 C3 H3 118.8 . .
C4 C3 H3 118.8 . .
Pd1 C3 H3 122.8 . .
C3 C4 C5 127.0(3) . .
C3 C4 Pd1 66.85(18) . .
C5 C4 Pd1 109.4(2) . .
C3 C4 H4 116.5 . .
C5 C4 H4 116.5 . .
Pd1 C4 H4 93.9 . .
C6 C5 C4 129.8(3) . .
C6 C5 H5 115.1 . .
C4 C5 H5 115.1 . .
C5 C6 C7 127.6(3) . .
C5 C6 H6 116.2 . .
C7 C6 H6 116.2 . .
C1 C7 C6 127.7(3) . .
C1 C7 H7 116.2 . .
C6 C7 H7 116.2 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C8 N1 C12 121.5(3) . .
C8 N1 C1 119.5(3) . .
C12 N1 C1 119.0(3) . .
F1 P1 F6 89.82(17) . .
F1 P1 F4 90.39(17) . .
F6 P1 F4 91.53(16) . .
F1 P1 F5 89.62(16) . .
F6 P1 F5 179.33(16) . .
F4 P1 F5 88.83(15) . .
F1 P1 F3 90.42(17) . .
F6 P1 F3 88.02(16) . .
F4 P1 F3 179.06(17) . .
F5 P1 F3 91.63(15) . .
F1 P1 F2 179.9(2) . .
F6 P1 F2 90.26(15) . .
F4 P1 F2 89.70(16) . .
F5 P1 F2 90.31(14) . .
F3 P1 F2 89.49(15) . .
O1 C15 C16 120.9(3) . 2_656
O1 C15 C16 120.9(3) . .
C16 C15 C16 118.2(6) 2_656 .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C3 2.073(3) .
Pd1 C4 2.166(3) .
Pd1 C2 2.201(3) .
Pd1 Br1 2.5665(4) .
Pd1 Br1 2.5786(4) 2_655
Pd1 Pd1 3.0021(4) 2_655
Br1 Pd1 2.5786(4) 2_655
C12 N1 1.355(4) .
C12 C11 1.375(5) .
C12 H12 0.9500 .
C11 C10 1.400(5) .
C11 C14 1.490(5) .
C10 C9 1.378(5) .
C10 H10 0.9500 .
C9 C8 1.398(5) .
C9 C13 1.503(5) .
C8 N1 1.347(4) .
C8 H8 0.9500 .
C1 C7 1.354(5) .
C1 C2 1.456(5) .
C1 N1 1.457(4) .
C2 C3 1.402(5) .
C2 H2 0.9500 .
C3 C4 1.427(5) .
C3 H3 0.9500 .
C4 C5 1.429(5) .
C4 H4 0.9500 .
C5 C6 1.352(5) .
C5 H5 0.9500 .
C6 C7 1.426(5) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
P1 F1 1.572(2) .
P1 F6 1.583(3) .
P1 F4 1.583(3) .
P1 F5 1.587(2) .
P1 F3 1.588(3) .
P1 F2 1.589(2) .
O1 C15 1.219(7) .
C15 C16 1.473(5) 2_656
C15 C16 1.473(5) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
