#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:26:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178651 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/62/4076257.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_4076257
loop_
_publ_author_name
'Solé, Daniel'
'Vallverdú, Lluís'
'Solans, Xavier'
'Font-Bardia, Mercè'
'Bonjoch, Josep'
_publ_section_title
;
 Synthesis and Reactivity of Four-Membered Azapalladacycles Derived
 fromN,N-Dialkyl-2-iodoanilines:  Insertion Reactions of Carbenes
 into the Carbon−Palladium Bond
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1438
_journal_paper_doi               10.1021/om034270c
_journal_volume                  23
_journal_year                    2004
_chemical_formula_sum            'C70 H66 I2 N2 O4 P2 Pd2'
_chemical_formula_weight         1527.79
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.9260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5280(10)
_cell_length_b                   26.6000(10)
_cell_length_c                   12.8330(10)
_cell_measurement_temperature    293(2)
_cell_volume                     3182.3(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.867
_diffrn_measured_fraction_theta_max 0.867
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            27490
_diffrn_reflns_theta_full        31.55
_diffrn_reflns_theta_max         31.55
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.635
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.228
_refine_ls_extinction_expression Fc
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         9233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0490P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                6868
_reflns_number_total             9233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om034270csi20040114_041317.cif
_cod_data_source_block           8b
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4076257
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_calc_flag
_atom_site_refinement_flags
Pd Pd 0.257694(19) 0.152575(6) 0.397099(13) 0.03893(6) Uani 1 d .
I I 0.23837(2) 0.103171(7) 0.581927(13) 0.05778(7) Uani 1 d .
P P 0.12448(7) 0.09330(2) 0.29738(5) 0.04071(13) Uani 1 d .
N N 0.3969(2) 0.21178(7) 0.47717(14) 0.0427(4) Uani 1 d .
O1 O 0.15063(19) 0.19985(6) 0.19533(14) 0.0563(5) Uani 1 d .
C1 C 0.4409(3) 0.24103(9) 0.3939(2) 0.0473(5) Uani 1 d .
C2 C 0.5466(3) 0.27725(10) 0.4142(2) 0.0589(7) Uani 1 d .
H2 H 0.5948 0.2837 0.4836 0.071 Uiso 1 calc R
C3 C 0.5796(3) 0.30339(10) 0.3311(3) 0.0673(8) Uani 1 d .
H3 H 0.6514 0.3276 0.3449 0.081 Uiso 1 calc R
C4 C 0.5099(3) 0.29509(11) 0.2272(3) 0.0673(8) Uani 1 d .
H4 H 0.5361 0.3127 0.1715 0.081 Uiso 1 calc R
C5 C 0.3999(3) 0.26006(10) 0.2073(2) 0.0556(6) Uani 1 d .
H5 H 0.3493 0.2545 0.1382 0.067 Uiso 1 calc R
C6 C 0.3665(3) 0.23362(8) 0.29095(19) 0.0437(5) Uani 1 d .
C7 C 0.2450(3) 0.19746(8) 0.27285(18) 0.0446(5) Uani 1 d .
C8 C 0.5241(3) 0.19047(10) 0.5502(2) 0.0557(6) Uani 1 d .
H8 H 0.4935 0.1713 0.6049 0.067 Uiso 1 calc R
H8A H 0.5856 0.2173 0.5823 0.067 Uiso 1 calc R
H8B H 0.5755 0.1691 0.5109 0.067 Uiso 1 calc R
C9 C 0.3200(3) 0.24487(9) 0.5428(2) 0.0514(6) Uani 1 d .
H9 H 0.2868 0.2244 0.5955 0.062 Uiso 1 calc R
H9A H 0.3867 0.2695 0.5804 0.062 Uiso 1 calc R
C10 C 0.1962(3) 0.27118(9) 0.4770(2) 0.0513(6) Uani 1 d .
C11 C 0.0677(3) 0.24769(11) 0.4468(2) 0.0611(7) Uani 1 d .
H11 H 0.0567 0.2152 0.4707 0.073 Uiso 1 calc R
C12 C -0.0467(4) 0.27102(15) 0.3815(3) 0.0817(10) Uani 1 d .
H12 H -0.1341 0.2544 0.3623 0.098 Uiso 1 calc R
C13 C -0.0321(5) 0.31797(17) 0.3454(3) 0.0927(13) Uani 1 d .
H13 H -0.1089 0.3335 0.3004 0.111 Uiso 1 calc R
C14 C 0.0939(5) 0.34226(15) 0.3746(3) 0.0922(13) Uani 1 d .
H14 H 0.1037 0.3747 0.3502 0.111 Uiso 1 calc R
C15 C 0.2089(4) 0.31917(12) 0.4408(3) 0.0747(9) Uani 1 d .
H16 H 0.2954 0.3363 0.4609 0.090 Uiso 1 calc R
C16 C 0.1735(3) 0.02874(9) 0.32964(18) 0.0457(5) Uani 1 d .
C17 C 0.3166(3) 0.01774(12) 0.3636(2) 0.0642(7) Uani 1 d .
H17 H 0.3827 0.0436 0.3827 0.077 Uiso 1 calc R
C18 C 0.3621(5) -0.03137(14) 0.3692(3) 0.0870(11) Uani 1 d .
H18 H 0.4594 -0.0386 0.3896 0.104 Uiso 1 calc R
C19 C 0.2646(5) -0.07004(12) 0.3448(3) 0.0880(12) Uani 1 d .
H19 H 0.2957 -0.1033 0.3486 0.106 Uiso 1 calc R
C20 C 0.1244(5) -0.05931(11) 0.3155(3) 0.0851(11) Uani 1 d .
H20 H 0.0582 -0.0854 0.3009 0.102 Uiso 1 calc R
C21 C 0.0767(4) -0.01010(10) 0.3066(2) 0.0695(8) Uani 1 d .
H21 H -0.0207 -0.0033 0.2852 0.083 Uiso 1 calc R
C22 C 0.1253(3) 0.09096(8) 0.15547(18) 0.0489(6) Uani 1 d .
C23 C 0.2498(3) 0.10116(11) 0.1229(2) 0.0609(7) Uani 1 d .
H23 H 0.3292 0.1129 0.1716 0.073 Uiso 1 calc R
C24 C 0.2585(4) 0.09403(12) 0.0159(3) 0.0768(9) Uani 1 d .
H24 H 0.3433 0.1009 -0.0066 0.092 Uiso 1 calc R
C25 C 0.1402(5) 0.07677(12) -0.0552(3) 0.0836(11) Uani 1 d .
H25 H 0.1450 0.0721 -0.1262 0.100 Uiso 1 calc R
C26 C 0.0173(5) 0.06654(12) -0.0232(2) 0.0825(11) Uani 1 d .
H26 H -0.0621 0.0547 -0.0717 0.099 Uiso 1 calc R
C27 C 0.0099(4) 0.07365(11) 0.0819(2) 0.0669(8) Uani 1 d .
H27 H -0.0754 0.0666 0.1035 0.080 Uiso 1 calc R
C28 C -0.0609(3) 0.10257(10) 0.3048(2) 0.0520(6) Uani 1 d .
C29 C -0.1214(3) 0.07857(17) 0.3785(2) 0.0837(11) Uani 1 d .
H29 H -0.0703 0.0546 0.4239 0.100 Uiso 1 calc R
C30 C -0.2636(5) 0.0911(2) 0.3842(3) 0.1120(17) Uani 1 d .
H30 H -0.3073 0.0749 0.4334 0.134 Uiso 1 calc R
C31 C -0.3361(4) 0.1259(2) 0.3196(4) 0.0993(14) Uani 1 d .
H31 H -0.4302 0.1333 0.3238 0.119 Uiso 1 calc R
C32 C -0.2757(4) 0.15003(15) 0.2496(4) 0.0960(14) Uani 1 d .
H32 H -0.3274 0.1746 0.2062 0.22(3) Uiso 1 calc R
C33 C -0.1380(3) 0.13919(12) 0.2406(3) 0.0782(10) Uani 1 d .
H33 H -0.0965 0.1564 0.1915 0.094 Uiso 1 calc R
O1W O 0.6638(13) 0.0444(4) 0.0370(10) 0.211(4) Uiso 0.50 d P
O2W O 0.5000 0.0000 0.0000 0.1109(13) Uiso 1 d S
C1W C 0.5841(14) 0.0151(5) 0.0726(11) 0.135(4) Uiso 0.50 d P
C2W C 0.5835(19) -0.0068(6) 0.1797(14) 0.137(5) Uiso 0.50 d P
C3W C 0.4991(15) 0.0102(4) -0.1280(11) 0.128(4) Uiso 0.50 d P
C4W C 0.3738(17) -0.0122(6) -0.1837(13) 0.146(6) Uiso 0.50 d P
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'
I I -0.4742 1.8119 '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'
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
C7 Pd N 82.72(8) . .
C7 Pd P 91.80(7) . .
N Pd P 173.29(5) . .
C7 Pd I 168.76(7) . .
N Pd I 94.67(5) . .
P Pd I 91.444(17) . .
C16 P C28 109.12(12) . .
C16 P C22 98.18(10) . .
C28 P C22 105.26(13) . .
C16 P Pd 116.57(8) . .
C28 P Pd 108.50(8) . .
C22 P Pd 118.26(8) . .
C1 N C8 110.3(2) . .
C1 N C9 110.22(19) . .
C8 N C9 107.33(19) . .
C1 N Pd 106.32(13) . .
C8 N Pd 111.14(15) . .
C9 N Pd 111.53(15) . .
C6 C1 C2 119.4(2) . .
C6 C1 N 117.3(2) . .
C2 C1 N 123.1(2) . .
C3 C2 C1 119.1(3) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 122.2(3) . .
C2 C3 H3 118.9 . .
C4 C3 H3 118.9 . .
C3 C4 C5 118.7(3) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C6 C5 C4 119.3(3) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
C5 C6 C1 121.3(2) . .
C5 C6 C7 120.5(2) . .
C1 C6 C7 118.2(2) . .
O1 C7 C6 121.5(2) . .
O1 C7 Pd 127.80(19) . .
C6 C7 Pd 110.45(16) . .
N C8 H8 109.5 . .
N C8 H8A 109.5 . .
H8 C8 H8A 109.5 . .
N C8 H8B 109.5 . .
H8 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C10 C9 N 112.3(2) . .
C10 C9 H9 109.1 . .
N C9 H9 109.1 . .
C10 C9 H9A 109.1 . .
N C9 H9A 109.1 . .
H9 C9 H9A 107.9 . .
C11 C10 C15 118.0(3) . .
C11 C10 C9 120.8(3) . .
C15 C10 C9 121.2(3) . .
C10 C11 C12 121.3(3) . .
C10 C11 H11 119.3 . .
C12 C11 H11 119.3 . .
C13 C12 C11 120.1(4) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 C12 119.8(3) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C13 C14 C15 120.4(3) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C10 C15 C14 120.4(4) . .
C10 C15 H16 119.8 . .
C14 C15 H16 119.8 . .
C17 C16 C21 119.0(2) . .
C17 C16 P 117.9(2) . .
C21 C16 P 122.3(2) . .
C18 C17 C16 120.0(3) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 120.5(4) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C20 C19 C18 119.4(3) . .
C20 C19 H19 120.3 . .
C18 C19 H19 120.3 . .
C19 C20 C21 121.1(3) . .
C19 C20 H20 119.5 . .
C21 C20 H20 119.5 . .
C16 C21 C20 119.9(3) . .
C16 C21 H21 120.0 . .
C20 C21 H21 120.0 . .
C23 C22 C27 118.7(3) . .
C23 C22 P 118.9(2) . .
C27 C22 P 122.0(2) . .
C22 C23 C24 120.2(3) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
C25 C24 C23 119.2(4) . .
C25 C24 H24 120.4 . .
C23 C24 H24 120.4 . .
C26 C25 C24 120.7(3) . .
C26 C25 H25 119.6 . .
C24 C25 H25 119.6 . .
C25 C26 C27 119.7(3) . .
C25 C26 H26 120.2 . .
C27 C26 H26 120.2 . .
C22 C27 C26 121.5(3) . .
C22 C27 H27 119.2 . .
C26 C27 H27 119.2 . .
C29 C28 C33 119.6(3) . .
C29 C28 P 122.1(2) . .
C33 C28 P 118.0(2) . .
C28 C29 C30 118.2(4) . .
C28 C29 H29 120.9 . .
C30 C29 H29 120.9 . .
C31 C30 C29 120.7(4) . .
C31 C30 H30 119.7 . .
C29 C30 H30 119.7 . .
C32 C31 C30 120.9(4) . .
C32 C31 H31 119.5 . .
C30 C31 H31 119.5 . .
C31 C32 C33 120.7(4) . .
C31 C32 H32 119.6 . .
C33 C32 H32 119.6 . .
C32 C33 C28 119.8(4) . .
C32 C33 H33 120.1 . .
C28 C33 H33 120.1 . .
C1W O2W C1W 180.000(3) . 3_655
C1W O2W C3W 53.5(8) . 3_655
C1W O2W C3W 126.5(8) 3_655 3_655
C1W O2W C3W 126.5(8) . .
C1W O2W C3W 53.5(8) 3_655 .
C3W O2W C3W 180.0 3_655 .
O2W C1W O1W 107.1(12) . .
O2W C1W C3W 82.4(11) . 3_655
O1W C1W C3W 168.4(15) . 3_655
O2W C1W C4W 143.0(14) . 3_655
O1W C1W C4W 109.9(14) . 3_655
C3W C1W C4W 60.9(11) 3_655 3_655
O2W C1W C2W 117.9(14) . .
O1W C1W C2W 134.7(15) . .
C3W C1W C2W 37.5(8) 3_655 .
C4W C1W C2W 25.5(9) 3_655 .
C4W C2W C3W 125(3) 3_655 3_655
C4W C2W C1W 69(2) 3_655 .
C3W C2W C1W 62.7(14) 3_655 .
C2W C3W C1W 79.8(15) 3_655 3_655
C2W C3W C4W 22.4(14) 3_655 .
C1W C3W C4W 61.4(9) 3_655 .
C2W C3W O2W 121.5(16) 3_655 .
C1W C3W O2W 44.1(7) 3_655 .
C4W C3W O2W 105.4(10) . .
C2W C4W C3W 33(2) 3_655 .
C2W C4W C1W 85(3) 3_655 3_655
C3W C4W C1W 57.7(9) . 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd C7 1.976(2) .
Pd N 2.1752(19) .
Pd P 2.2503(6) .
Pd I 2.7509(3) .
P C16 1.805(2) .
P C28 1.806(3) .
P C22 1.824(2) .
N C1 1.452(3) .
N C8 1.483(3) .
N C9 1.509(3) .
O1 C7 1.197(3) .
C1 C6 1.379(3) .
C1 C2 1.379(4) .
C2 C3 1.364(4) .
C2 H2 0.9300 .
C3 C4 1.379(4) .
C3 H3 0.9300 .
C4 C5 1.386(4) .
C4 H4 0.9300 .
C5 C6 1.375(3) .
C5 H5 0.9300 .
C6 C7 1.486(3) .
C8 H8 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C9 C10 1.477(3) .
C9 H9 0.9700 .
C9 H9A 0.9700 .
C10 C11 1.358(4) .
C10 C15 1.372(4) .
C11 C12 1.378(4) .
C11 H11 0.9300 .
C12 C13 1.349(5) .
C12 H12 0.9300 .
C13 C14 1.347(6) .
C13 H13 0.9300 .
C14 C15 1.384(5) .
C14 H14 0.9300 .
C15 H16 0.9300 .
C16 C17 1.374(4) .
C16 C21 1.376(4) .
C17 C18 1.373(4) .
C17 H17 0.9300 .
C18 C19 1.378(6) .
C18 H18 0.9300 .
C19 C20 1.341(6) .
C19 H19 0.9300 .
C20 C21 1.383(4) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C22 C23 1.364(4) .
C22 C27 1.372(4) .
C23 C24 1.406(4) .
C23 H23 0.9300 .
C24 C25 1.374(5) .
C24 H24 0.9300 .
C25 C26 1.346(6) .
C25 H25 0.9300 .
C26 C27 1.378(4) .
C26 H26 0.9300 .
C27 H27 0.9300 .
C28 C29 1.364(4) .
C28 C33 1.384(4) .
C29 C30 1.412(5) .
C29 H29 0.9300 .
C30 C31 1.335(6) .
C30 H30 0.9300 .
C31 C32 1.329(6) .
C31 H31 0.9300 .
C32 C33 1.372(5) .
C32 H32 0.9300 .
C33 H33 0.9300 .
O1W C1W 1.240(14) .
O2W C1W 1.167(13) .
O2W C1W 1.167(13) 3_655
O2W C3W 1.663(13) 3_655
O2W C3W 1.663(13) .
C1W C3W 1.348(16) 3_655
C1W C4W 1.401(19) 3_655
C1W C2W 1.49(2) .
C2W C4W 0.64(2) 3_655
C2W C3W 0.923(18) 3_655
C3W C2W 0.923(18) 3_655
C3W C1W 1.348(16) 3_655
C3W C4W 1.39(2) .
C4W C2W 0.64(2) 3_655
C4W C1W 1.401(19) 3_655
