#------------------------------------------------------------------------------
#$Date: 2016-03-21 12:56:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178689 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/00/4080095.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_4080095
loop_
_publ_author_name
'Garc\?ía-López, José-Antonio'
'Oliva-Madrid, Mar\?ía-José'
'Saura-Llamas, Isabel'
'Bautista, Delia'
'Vicente, José'
_publ_section_title
;
 Room-Temperature Isolation of Palladium(II) Organocarbonyl Intermediates
 in the Synthesis of Eight-Membered Lactams after Alkyne/CO Sequential
 Insertions
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1094
_journal_paper_doi               10.1021/om301241n
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C40 H44 Cl2 N2 O4 Pd2'
_chemical_formula_weight         900.47
_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                 98.861(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5407(10)
_cell_length_b                   12.1740(15)
_cell_length_c                   18.682(2)
_cell_measurement_reflns_used    3159
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.51
_cell_measurement_theta_min      2.21
_cell_volume                     1919.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12070
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.9258
_exptl_absorpt_correction_T_min  0.7902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.915
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment
'NH2 free with SADI, rigid methyls, other riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0539
_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)+(0.0381P)²+2.4715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                3949
_reflns_number_total             4479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om301241n_si_002.cif
_cod_data_source_block           jakxs076
_cod_original_cell_volume        1919.2(4)
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4080095
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
Pd1 Pd 0.09673(4) 0.06875(3) 0.074696(16) 0.01719(10) Uani 1 1 d .
Cl1 Cl -0.15101(12) -0.03188(10) 0.04168(5) 0.0266(2) Uani 1 1 d .
N1 N 0.0525(4) 0.1110(3) 0.17637(18) 0.0196(7) Uani 1 1 d D
H01A H -0.045(4) 0.119(3) 0.174(2) 0.007(10) Uiso 1 1 d D
H01B H 0.092(5) 0.173(3) 0.184(3) 0.028(14) Uiso 1 1 d D
C1 C 0.4232(5) -0.0230(3) 0.1393(2) 0.0194(8) Uani 1 1 d .
C2 C 0.3483(5) -0.0585(4) 0.1977(2) 0.0214(9) Uani 1 1 d .
C3 C 0.3455(5) -0.1709(4) 0.2112(2) 0.0259(10) Uani 1 1 d .
H3 H 0.2985 -0.1965 0.2510 0.031 Uiso 1 1 calc R
C4 C 0.4097(6) -0.2464(4) 0.1683(2) 0.0311(11) Uani 1 1 d .
H4 H 0.4036 -0.3227 0.1781 0.037 Uiso 1 1 calc R
C5 C 0.4819(5) -0.2111(4) 0.1117(3) 0.0303(10) Uani 1 1 d .
H5 H 0.5269 -0.2629 0.0827 0.036 Uiso 1 1 calc R
C6 C 0.4888(5) -0.1001(4) 0.0971(2) 0.0251(9) Uani 1 1 d .
H6 H 0.5388 -0.0759 0.0578 0.030 Uiso 1 1 calc R
C7 C 0.4290(5) 0.0961(3) 0.1199(2) 0.0176(8) Uani 1 1 d .
C8 C 0.2957(4) 0.1509(3) 0.0956(2) 0.0166(8) Uani 1 1 d .
C9 C 0.1043(5) 0.0392(4) 0.2406(2) 0.0237(9) Uani 1 1 d .
C10 C 0.2844(5) 0.0193(4) 0.2489(2) 0.0229(9) Uani 1 1 d .
H10A H 0.3358 0.0915 0.2449 0.027 Uiso 1 1 calc R
H10B H 0.3197 -0.0077 0.2988 0.027 Uiso 1 1 calc R
C11 C 0.0072(6) -0.0666(4) 0.2296(3) 0.0315(10) Uani 1 1 d .
H11A H -0.1060 -0.0486 0.2225 0.047 Uiso 1 1 calc R
H11B H 0.0329 -0.1136 0.2724 0.047 Uiso 1 1 calc R
H11C H 0.0324 -0.1054 0.1869 0.047 Uiso 1 1 calc R
C12 C 0.0676(6) 0.1013(5) 0.3077(2) 0.0354(12) Uani 1 1 d .
H12A H 0.1334 0.1675 0.3149 0.053 Uiso 1 1 calc R
H12B H 0.0906 0.0539 0.3504 0.053 Uiso 1 1 calc R
H12C H -0.0445 0.1222 0.3004 0.053 Uiso 1 1 calc R
C13 C 0.5898(5) 0.1463(3) 0.1266(2) 0.0184(8) Uani 1 1 d .
O1 O 0.7002(3) 0.1212(2) 0.17139(15) 0.0212(6) Uani 1 1 d .
C14 C 0.7482(5) 0.2753(4) 0.0746(2) 0.0270(10) Uani 1 1 d .
H14A H 0.7922 0.2987 0.1238 0.041 Uiso 1 1 calc R
H14B H 0.7333 0.3395 0.0427 0.041 Uiso 1 1 calc R
H14C H 0.8213 0.2237 0.0567 0.041 Uiso 1 1 calc R
O2 O 0.5979(3) 0.2223(2) 0.07558(16) 0.0272(7) Uani 1 1 d .
C21 C 0.2781(5) 0.2711(3) 0.0882(2) 0.0197(9) Uani 1 1 d .
C22 C 0.3214(5) 0.3373(4) 0.1489(2) 0.0233(9) Uani 1 1 d .
H22 H 0.3671 0.3045 0.1934 0.028 Uiso 1 1 calc R
C23 C 0.2991(6) 0.4500(4) 0.1455(2) 0.0283(10) Uani 1 1 d .
H23 H 0.3282 0.4936 0.1876 0.034 Uiso 1 1 calc R
C24 C 0.2348(6) 0.4989(4) 0.0811(3) 0.0342(11) Uani 1 1 d .
H24 H 0.2218 0.5763 0.0782 0.041 Uiso 1 1 calc R
C25 C 0.1894(7) 0.4339(4) 0.0209(3) 0.0379(12) Uani 1 1 d .
H25 H 0.1432 0.4672 -0.0233 0.045 Uiso 1 1 calc R
C26 C 0.2101(6) 0.3213(4) 0.0238(2) 0.0289(10) Uani 1 1 d .
H26 H 0.1778 0.2781 -0.0182 0.035 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'
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'
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
C8 Pd1 N1 88.03(15) . .
C8 Pd1 Cl1 89.60(11) . 3
N1 Pd1 Cl1 176.55(11) . 3
C8 Pd1 Cl1 176.89(11) . .
N1 Pd1 Cl1 94.78(11) . .
Cl1 Pd1 Cl1 87.53(4) 3 .
Pd1 Cl1 Pd1 92.47(4) 3 .
C9 N1 Pd1 121.4(3) . .
C6 C1 C2 119.9(4) . .
C6 C1 C7 118.8(4) . .
C2 C1 C7 121.3(4) . .
C3 C2 C1 117.6(4) . .
C3 C2 C10 119.0(4) . .
C1 C2 C10 123.2(4) . .
C4 C3 C2 121.8(4) . .
C5 C4 C3 120.1(4) . .
C4 C5 C6 119.8(4) . .
C5 C6 C1 120.7(4) . .
C8 C7 C13 123.3(4) . .
C8 C7 C1 120.5(4) . .
C13 C7 C1 116.2(3) . .
C7 C8 C21 126.5(4) . .
C7 C8 Pd1 118.7(3) . .
C21 C8 Pd1 114.5(3) . .
N1 C9 C11 107.3(3) . .
N1 C9 C12 107.1(4) . .
C11 C9 C12 110.5(4) . .
N1 C9 C10 109.8(3) . .
C11 C9 C10 113.2(4) . .
C12 C9 C10 108.7(4) . .
C2 C10 C9 119.2(3) . .
O1 C13 O2 123.5(4) . .
O1 C13 C7 124.6(4) . .
O2 C13 C7 111.8(3) . .
C13 O2 C14 117.6(3) . .
C22 C21 C26 118.2(4) . .
C22 C21 C8 119.2(4) . .
C26 C21 C8 122.6(4) . .
C23 C22 C21 121.2(4) . .
C24 C23 C22 120.1(4) . .
C23 C24 C25 119.2(4) . .
C24 C25 C26 121.2(4) . .
C25 C26 C21 120.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C8 1.958(4) .
Pd1 N1 2.058(4) .
Pd1 Cl1 2.3354(11) 3
Pd1 Cl1 2.4406(11) .
Cl1 Pd1 2.3354(11) 3
N1 C9 1.496(5) .
C1 C6 1.399(6) .
C1 C2 1.414(6) .
C1 C7 1.497(6) .
C2 C3 1.392(6) .
C2 C10 1.508(6) .
C3 C4 1.387(6) .
C4 C5 1.372(7) .
C5 C6 1.382(6) .
C7 C8 1.338(5) .
C7 C13 1.491(5) .
C8 C21 1.475(6) .
C9 C11 1.529(6) .
C9 C12 1.536(6) .
C9 C10 1.541(6) .
C13 O1 1.200(5) .
C13 O2 1.337(5) .
C14 O2 1.439(5) .
C21 C22 1.393(6) .
C21 C26 1.395(6) .
C22 C23 1.386(6) .
C23 C24 1.378(6) .
C24 C25 1.380(7) .
C25 C26 1.382(6) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H01A O1 0.83(3) 2.17(3) 2.999(4) 174(4) 1_455
