#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113179.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_4113179
loop_
_publ_author_name
'Gereon Altenhoff'
'Richard Goddard'
'Christian W. Lehmann'
'Frank Glorius'
_publ_section_title
;
 Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands
 with Restricted Flexibility for Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15195
_journal_page_last               15201
_journal_paper_doi               10.1021/ja045349r
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        dichloromethane/hexane/ethylacetate
_chemical_formula_moiety         'C38 H56 Cl4 N4 O4 Pd2'
_chemical_formula_sum            'C38 H56 Cl4 N4 O4 Pd2'
_chemical_formula_weight         987.47
_chemical_name_common            ((Ibiox7)PdCl2)2
_chemical_name_systematic
; 
 Bis[Dispiro(cycloheptane-1,3'-(1,3)oxazolo(3',2':3,4)-
 imidazolo(5,1-b)(1,3)oxazole-7',1"-cycloheptane-5'-ylidine)-dichloro-
 palladium] 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0
_cell_angle_beta                 97.3395(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   13.2368(2)
_cell_length_b                   11.6748(1)
_cell_length_c                   13.6306(1)
_cell_measurement_reflns_used    56611
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.91
_cell_volume                     2089.17(4)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35433
_diffrn_reflns_theta_full        31.01
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         3.48
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.160
_exptl_absorpt_correction_T_max  0.80445
_exptl_absorpt_correction_T_min  0.67816
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP, Siemens (1995)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.371
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         6612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0282
_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)+(0.0235P)²+2.3477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0687
_reflns_number_gt                6088
_reflns_number_total             6612
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja045349rsi20040802_024156.cif
_cod_data_source_block           ((Ibiox7)PdCl2)2
_cod_depositor_comments
;
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_database_code               4113179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.47600(13) 0.38517(13) 0.22613(13) 0.0215(3) Uani 1 1 d .
C2 C 0.31647(15) 0.49468(15) 0.28105(15) 0.0284(4) Uani 1 1 d .
C3 C 0.3277(2) 0.5396(2) 0.38852(17) 0.0414(5) Uani 1 1 d .
H3A H 0.3607 0.6139 0.3928 0.050 Uiso 1 1 calc R
H3B H 0.2614 0.5470 0.4110 0.050 Uiso 1 1 calc R
C4 C 0.44931(17) 0.40881(17) 0.38609(14) 0.0313(4) Uani 1 1 d .
C5 C 0.52999(16) 0.34018(17) 0.38613(14) 0.0301(4) Uani 1 1 d .
C6 C 0.65512(16) 0.21243(16) 0.38802(14) 0.0299(4) Uani 1 1 d .
H6A H 0.6246 0.1368 0.3838 0.036 Uiso 1 1 calc R
H6B H 0.7262 0.2051 0.4152 0.036 Uiso 1 1 calc R
C7 C 0.64548(14) 0.26880(14) 0.28431(13) 0.0242(3) Uani 1 1 d .
C8 C 0.30600(18) 0.59585(16) 0.20946(18) 0.0351(4) Uani 1 1 d .
H8A H 0.3739 0.6232 0.2026 0.042 Uiso 1 1 calc R
H8B H 0.2712 0.6570 0.2397 0.042 Uiso 1 1 calc R
C9 C 0.25009(17) 0.5756(2) 0.10575(18) 0.0395(5) Uani 1 1 d .
H9A H 0.2689 0.5009 0.0829 0.047 Uiso 1 1 calc R
H9B H 0.2724 0.6325 0.0613 0.047 Uiso 1 1 calc R
C10 C 0.13403(19) 0.5816(2) 0.1004(2) 0.0484(6) Uani 1 1 d .
H10A H 0.1163 0.6491 0.1359 0.058 Uiso 1 1 calc R
H10B H 0.1054 0.5909 0.0317 0.058 Uiso 1 1 calc R
C11 C 0.08489(17) 0.4779(2) 0.1422(2) 0.0434(5) Uani 1 1 d .
H11A H 0.0954 0.4121 0.1013 0.052 Uiso 1 1 calc R
H11B H 0.0121 0.4911 0.1371 0.052 Uiso 1 1 calc R
C12 C 0.12370(17) 0.4482(2) 0.24942(19) 0.0383(5) Uani 1 1 d .
H12A H 0.0793 0.3908 0.2725 0.046 Uiso 1 1 calc R
H12B H 0.1201 0.5161 0.2899 0.046 Uiso 1 1 calc R
C13 C 0.23365(15) 0.40278(15) 0.26379(16) 0.0289(4) Uani 1 1 d .
H13A H 0.2412 0.3509 0.3198 0.035 Uiso 1 1 calc R
H13B H 0.2447 0.3588 0.2057 0.035 Uiso 1 1 calc R
C14 C 0.72431(15) 0.36472(16) 0.28098(16) 0.0322(4) Uani 1 1 d .
H14A H 0.7009 0.4153 0.2263 0.039 Uiso 1 1 calc R
H14B H 0.7269 0.4091 0.3414 0.039 Uiso 1 1 calc R
C15 C 0.83230(16) 0.3256(2) 0.2695(2) 0.0450(6) Uani 1 1 d .
H15A H 0.8803 0.3823 0.2993 0.054 Uiso 1 1 calc R
H15B H 0.8461 0.2542 0.3052 0.054 Uiso 1 1 calc R
C16 C 0.84927(19) 0.3081(2) 0.1624(2) 0.0550(8) Uani 1 1 d .
H16A H 0.8290 0.3777 0.1262 0.066 Uiso 1 1 calc R
H16B H 0.9217 0.2980 0.1604 0.066 Uiso 1 1 calc R
C17 C 0.7938(2) 0.2083(2) 0.1084(2) 0.0533(7) Uani 1 1 d .
H17A H 0.8208 0.1378 0.1390 0.064 Uiso 1 1 calc R
H17B H 0.8091 0.2084 0.0406 0.064 Uiso 1 1 calc R
C18 C 0.67726(19) 0.2075(2) 0.10652(17) 0.0394(5) Uani 1 1 d .
H18A H 0.6510 0.2829 0.0873 0.047 Uiso 1 1 calc R
H18B H 0.6482 0.1535 0.0566 0.047 Uiso 1 1 calc R
C19 C 0.64237(16) 0.17534(16) 0.20533(15) 0.0291(4) Uani 1 1 d .
H19A H 0.6842 0.1120 0.2329 0.035 Uiso 1 1 calc R
H19B H 0.5729 0.1475 0.1923 0.035 Uiso 1 1 calc R
Cl1 Cl 0.37545(4) 0.23042(4) 0.07308(3) 0.02802(9) Uani 1 1 d .
Cl2 Cl 0.55326(4) 0.57193(4) 0.09408(3) 0.02833(10) Uani 1 1 d .
N1 N 0.41656(12) 0.43487(13) 0.28761(11) 0.0250(3) Uani 1 1 d .
N2 N 0.54524(12) 0.32575(12) 0.28813(11) 0.0234(3) Uani 1 1 d .
O1 O 0.38967(14) 0.45578(15) 0.44884(11) 0.0423(4) Uani 1 1 d .
O2 O 0.60182(13) 0.28692(13) 0.45035(10) 0.0370(3) Uani 1 1 d .
Pd Pd 0.463461(9) 0.399340(10) 0.083085(9) 0.01919(4) Uani 1 1 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'
Cl Cl 0.1484 0.1585 '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'
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_3
_geom_angle_publ_flag
N1 C1 N2 103.53(15) . y
N1 C1 Pd 127.15(12) . y
N2 C1 Pd 129.32(14) . y
N1 C2 C8 114.09(17) . y
N1 C2 C13 107.13(14) . y
C8 C2 C13 116.06(17) . y
N1 C2 C3 97.17(15) . y
C8 C2 C3 109.49(16) . y
C13 C2 C3 111.33(18) . y
O1 C3 C2 106.60(16) . y
C5 C4 O1 140.79(18) . y
C5 C4 N1 106.41(17) . y
O1 C4 N1 112.75(17) . y
C4 C5 O2 140.28(19) . y
C4 C5 N2 106.70(16) . y
O2 C5 N2 112.91(18) . y
O2 C6 C7 106.76(14) . y
N2 C7 C19 113.50(14) . y
N2 C7 C14 106.68(14) . y
C19 C7 C14 117.18(17) . y
N2 C7 C6 97.32(15) . y
C19 C7 C6 109.31(14) . y
C14 C7 C6 111.08(15) . y
C2 C8 C9 117.74(17) . y
C8 C9 C10 113.7(2) . y
C11 C10 C9 114.92(19) . y
C10 C11 C12 115.6(2) . y
C11 C12 C13 113.44(19) . y
C2 C13 C12 115.18(16) . y
C15 C14 C7 115.68(17) . y
C16 C15 C14 113.18(19) . y
C17 C16 C15 116.6(2) . y
C16 C17 C18 115.8(2) . y
C19 C18 C17 113.75(19) . y
C18 C19 C7 117.53(17) . y
Pd Cl2 Pd 94.282(15) 3_665 y
C1 N1 C4 111.73(15) . y
C1 N1 C2 138.38(15) . y
C4 N1 C2 109.00(16) . y
C1 N2 C5 111.62(16) . y
C1 N2 C7 137.75(16) . y
C5 N2 C7 109.12(14) . y
C4 O1 C3 104.30(16) . y
C5 O2 C6 104.38(14) . y
C1 Pd Cl1 87.93(5) . y
C1 Pd Cl2 91.81(5) . y
Cl1 Pd Cl2 179.734(18) . y
C1 Pd Cl2 176.90(5) 3_665 y
Cl1 Pd Cl2 94.538(15) 3_665 y
Cl2 Pd Cl2 85.718(14) 3_665 y
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 N1 1.352(2) . y
C1 N2 1.356(2) . y
C1 Pd 1.9427(17) . y
C2 N1 1.490(2) . y
C2 C8 1.527(3) . y
C2 C13 1.530(3) . y
C2 C3 1.545(3) . y
C3 O1 1.460(3) . y
C4 C5 1.335(3) . y
C4 O1 1.352(3) . y
C4 N1 1.391(2) . y
C5 O2 1.358(2) . y
C5 N2 1.387(2) . y
C6 O2 1.459(3) . y
C6 C7 1.550(3) . y
C7 N2 1.491(2) . y
C7 C19 1.530(3) . y
C7 C14 1.535(3) . y
C8 C9 1.528(3) . y
C9 C10 1.530(3) . y
C10 C11 1.519(4) . y
C11 C12 1.526(4) . y
C12 C13 1.538(3) . y
C14 C15 1.528(3) . y
C15 C16 1.519(4) . y
C16 C17 1.517(4) . y
C17 C18 1.540(4) . y
C18 C19 1.525(3) . y
Cl1 Pd 2.2856(4) . y
Cl2 Pd 2.3344(4) . y
Cl2 Pd 2.4201(4) 3_665 y
Pd Cl2 2.4201(4) 3_665 y
