#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/37/4073752.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_4073752
loop_
_publ_author_name
'Stylianides, Neoklis'
'Danopoulos, Andreas A.'
'Pugh, David'
'Hancock, Fred'
'Zanotti-Gerosa, Antonio'
_publ_section_title
;
 Cyclometalated and Alkoxyphenyl-Substituted Palladium
 Imidazolin-2-ylidene Complexes. Synthetic, Structural, and Catalytic
 Studies
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              5627
_journal_paper_doi               10.1021/om700603d
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C21 H27 Cl N2 O2, 3(H2 O)'
_chemical_formula_sum            'C21 H33 Cl N2 O5'
_chemical_formula_weight         428.94
_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                 94.6060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4360(6)
_cell_length_b                   6.7896(2)
_cell_length_c                   21.5079(8)
_cell_measurement_reflns_used    5419
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2246.84(14)
_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_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'enCIFer (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1992)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23885
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.7416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0460
_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)+(0.0266P)²+1.7486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                3829
_reflns_number_total             5157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700603d-file002.cif
_cod_data_source_block           3f
_cod_original_sg_symbol_Hall     '-P2 yn'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4073752
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
Cl1 Cl -0.15497(3) 0.11706(7) 0.96990(2) 0.02924(13) Uani 1 1 d .
O1 O 0.09842(8) 0.03958(19) 0.67704(5) 0.0231(3) Uani 1 1 d .
O2 O -0.11509(8) 0.3723(2) 0.67127(6) 0.0260(3) Uani 1 1 d .
N1 N -0.04136(9) 0.3437(2) 0.79342(6) 0.0177(3) Uani 1 1 d .
N2 N 0.04368(9) 0.0812(2) 0.79645(6) 0.0179(3) Uani 1 1 d .
C2 C -0.01871(12) 0.3127(3) 0.86105(8) 0.0217(4) Uani 1 1 d .
H2A H -0.0716 0.3039 0.8841 0.026 Uiso 1 1 calc R
H2B H 0.0186 0.4206 0.8790 0.026 Uiso 1 1 calc R
C4 C 0.08829(11) -0.0903(3) 0.77805(8) 0.0189(4) Uani 1 1 d .
C3 C 0.03017(12) 0.1180(3) 0.86299(8) 0.0218(4) Uani 1 1 d .
H3A H 0.0863 0.1289 0.8884 0.026 Uiso 1 1 calc R
H3B H -0.0047 0.0117 0.8802 0.026 Uiso 1 1 calc R
C6 C 0.14999(11) -0.4070(3) 0.80671(9) 0.0241(4) Uani 1 1 d .
H6 H 0.1636 -0.5051 0.8375 0.029 Uiso 1 1 calc R
C1 C -0.00118(11) 0.2112(3) 0.76111(8) 0.0188(4) Uani 1 1 d .
H1 H -0.0042 0.2094 0.7168 0.023 Uiso 1 1 calc R
C17 C -0.17066(12) 0.7006(3) 0.69174(9) 0.0247(4) Uani 1 1 d .
H17 H -0.1932 0.7164 0.6496 0.030 Uiso 1 1 calc R
C5 C 0.10876(11) -0.2354(3) 0.82245(8) 0.0224(4) Uani 1 1 d .
H5 H 0.0942 -0.2164 0.8641 0.027 Uiso 1 1 calc R
C13 C -0.08986(10) 0.5118(3) 0.77146(8) 0.0188(4) Uani 1 1 d .
C7 C 0.17145(12) -0.4358(3) 0.74627(9) 0.0246(4) Uani 1 1 d .
H7 H 0.1983 -0.5553 0.7352 0.030 Uiso 1 1 calc R
C20 C -0.17714(13) 0.1594(3) 0.59242(9) 0.0284(4) Uani 1 1 d .
H20A H -0.2042 0.1499 0.5497 0.043 Uiso 1 1 calc R
H20B H -0.2165 0.1041 0.6215 0.043 Uiso 1 1 calc R
H20C H -0.1224 0.0856 0.5957 0.043 Uiso 1 1 calc R
C12 C 0.14792(14) 0.2382(3) 0.59667(9) 0.0331(5) Uani 1 1 d .
H12A H 0.0932 0.3116 0.5957 0.050 Uiso 1 1 calc R
H12B H 0.1698 0.2400 0.5551 0.050 Uiso 1 1 calc R
H12C H 0.1907 0.2996 0.6268 0.050 Uiso 1 1 calc R
C16 C -0.18286(12) 0.8484(3) 0.73471(9) 0.0256(4) Uani 1 1 d .
H16 H -0.2135 0.9646 0.7218 0.031 Uiso 1 1 calc R
C19 C -0.15925(12) 0.3726(3) 0.60841(8) 0.0229(4) Uani 1 1 d .
H19 H -0.2157 0.4448 0.6090 0.028 Uiso 1 1 calc R
C14 C -0.10429(11) 0.6600(3) 0.81425(8) 0.0219(4) Uani 1 1 d .
H14 H -0.0820 0.6457 0.8565 0.026 Uiso 1 1 calc R
C18 C -0.12574(11) 0.5295(3) 0.70961(8) 0.0210(4) Uani 1 1 d .
C15 C -0.15073(12) 0.8279(3) 0.79607(9) 0.0241(4) Uani 1 1 d .
H15 H -0.1604 0.9279 0.8256 0.029 Uiso 1 1 calc R
C9 C 0.11368(11) -0.1154(3) 0.71713(8) 0.0202(4) Uani 1 1 d .
C11 C 0.06944(13) -0.0817(3) 0.57153(9) 0.0352(5) Uani 1 1 d .
H11A H 0.0597 -0.2135 0.5882 0.053 Uiso 1 1 calc R
H11B H 0.0933 -0.0934 0.5308 0.053 Uiso 1 1 calc R
H11C H 0.0142 -0.0101 0.5668 0.053 Uiso 1 1 calc R
C8 C 0.15381(11) -0.2902(3) 0.70168(9) 0.0229(4) Uani 1 1 d .
H8 H 0.1693 -0.3101 0.6603 0.027 Uiso 1 1 calc R
C10 C 0.13269(12) 0.0286(3) 0.61580(8) 0.0226(4) Uani 1 1 d .
H10 H 0.1894 -0.0432 0.6196 0.027 Uiso 1 1 calc R
C21 C -0.10318(12) 0.4742(3) 0.56392(9) 0.0302(5) Uani 1 1 d .
H21A H -0.0475 0.4050 0.5636 0.045 Uiso 1 1 calc R
H21B H -0.0929 0.6107 0.5773 0.045 Uiso 1 1 calc R
H21C H -0.1327 0.4728 0.5219 0.045 Uiso 1 1 calc R
O3 O -0.03585(11) 0.7420(2) 0.96934(7) 0.0322(3) Uiso 1 1 d .
O4 O 0.14643(10) 0.4762(2) 0.96062(7) 0.0329(3) Uiso 1 1 d .
O5 O 0.25659(10) -0.3465(3) 0.57074(7) 0.0340(4) Uiso 1 1 d .
H31 H -0.0670(16) 0.851(4) 0.9700(11) 0.051(7) Uiso 1 1 d .
H41 H 0.1056(16) 0.422(4) 0.9821(11) 0.050(7) Uiso 1 1 d .
H42 H 0.160(2) 0.595(5) 0.9792(15) 0.093(11) Uiso 1 1 d .
H52 H 0.277(2) -0.450(5) 0.5438(16) 0.105(12) Uiso 1 1 d .
H51 H 0.2810(18) -0.230(4) 0.5585(13) 0.068(9) Uiso 1 1 d .
H32 H 0.016(2) 0.774(5) 0.9854(14) 0.087(10) Uiso 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'
N N 0.0061 0.0033 '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'
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
C9 O1 C10 118.18(14)
C18 O2 C19 119.10(14)
C1 N1 C13 128.87(14)
C1 N1 C2 109.60(14)
C13 N1 C2 120.99(14)
C1 N2 C4 128.88(15)
C1 N2 C3 109.52(14)
C4 N2 C3 120.92(14)
N1 C2 C3 103.15(14)
N1 C2 H2A 111.1
C3 C2 H2A 111.1
N1 C2 H2B 111.1
C3 C2 H2B 111.1
H2A C2 H2B 109.1
C5 C4 C9 119.24(17)
C5 C4 N2 118.46(15)
C9 C4 N2 122.29(16)
N2 C3 C2 103.16(14)
N2 C3 H3A 111.1
C2 C3 H3A 111.1
N2 C3 H3B 111.1
C2 C3 H3B 111.1
H3A C3 H3B 109.1
C7 C6 C5 119.97(17)
C7 C6 H6 120.0
C5 C6 H6 120.0
N1 C1 N2 113.46(15)
N1 C1 H1 123.3
N2 C1 H1 123.3
C16 C17 C18 120.75(17)
C16 C17 H17 119.6
C18 C17 H17 119.6
C6 C5 C4 120.83(17)
C6 C5 H5 119.6
C4 C5 H5 119.6
C14 C13 C18 119.47(17)
C14 C13 N1 117.85(15)
C18 C13 N1 122.64(16)
C6 C7 C8 120.05(18)
C6 C7 H7 120.0
C8 C7 H7 120.0
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C15 C16 C17 120.44(18)
C15 C16 H16 119.8
C17 C16 H16 119.8
O2 C19 C21 109.78(15)
O2 C19 C20 105.80(15)
C21 C19 C20 113.46(16)
O2 C19 H19 109.2
C21 C19 H19 109.2
C20 C19 H19 109.2
C15 C14 C13 120.93(17)
C15 C14 H14 119.5
C13 C14 H14 119.5
O2 C18 C17 124.52(16)
O2 C18 C13 116.58(16)
C17 C18 C13 118.88(17)
C16 C15 C14 119.43(18)
C16 C15 H15 120.3
C14 C15 H15 120.3
O1 C9 C8 124.24(16)
O1 C9 C4 116.51(16)
C8 C9 C4 119.23(16)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C7 C8 C9 120.56(17)
C7 C8 H8 119.7
C9 C8 H8 119.7
O1 C10 C12 105.90(15)
O1 C10 C11 109.40(15)
C12 C10 C11 113.87(17)
O1 C10 H10 109.2
C12 C10 H10 109.2
C11 C10 H10 109.2
C19 C21 H21A 109.5
C19 C21 H21B 109.5
H21A C21 H21B 109.5
C19 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
H31 O3 H32 106(2)
H41 O4 H42 106(2)
H52 O5 H51 107(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.369(2)
O1 C10 1.460(2)
O2 C18 1.366(2)
O2 C19 1.464(2)
N1 C1 1.321(2)
N1 C13 1.424(2)
N1 C2 1.483(2)
N2 C1 1.323(2)
N2 C4 1.425(2)
N2 C3 1.484(2)
C2 C3 1.521(3)
C2 H2A 0.9900
C2 H2B 0.9900
C4 C5 1.390(2)
C4 C9 1.408(2)
C3 H3A 0.9900
C3 H3B 0.9900
C6 C7 1.381(3)
C6 C5 1.383(3)
C6 H6 0.9500
C1 H1 0.9500
C17 C16 1.388(3)
C17 C18 1.391(3)
C17 H17 0.9500
C5 H5 0.9500
C13 C14 1.394(3)
C13 C18 1.404(2)
C7 C8 1.389(3)
C7 H7 0.9500
C20 C19 1.509(3)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C12 C10 1.505(3)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C16 C15 1.379(3)
C16 H16 0.9500
C19 C21 1.508(3)
C19 H19 1.0000
C14 C15 1.386(3)
C14 H14 0.9500
C15 H15 0.9500
C9 C8 1.391(3)
C11 C10 1.507(3)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C8 H8 0.9500
C10 H10 1.0000
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
O3 H31 0.88(3)
O3 H32 0.88(3)
O4 H41 0.89(3)
O4 H42 0.92(3)
O5 H52 0.98(4)
O5 H51 0.92(3)
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
C1 N1 C2 C3 -8.88(19)
C13 N1 C2 C3 178.84(15)
C1 N2 C4 C5 -161.03(17)
C3 N2 C4 C5 8.4(2)
C1 N2 C4 C9 20.3(3)
C3 N2 C4 C9 -170.23(16)
C1 N2 C3 C2 -8.86(19)
C4 N2 C3 C2 179.84(15)
N1 C2 C3 N2 10.18(17)
C13 N1 C1 N2 175.13(16)
C2 N1 C1 N2 3.6(2)
C4 N2 C1 N1 174.00(16)
C3 N2 C1 N1 3.6(2)
C7 C6 C5 C4 0.1(3)
C9 C4 C5 C6 -3.0(3)
N2 C4 C5 C6 178.32(16)
C1 N1 C13 C14 -161.39(17)
C2 N1 C13 C14 9.3(2)
C1 N1 C13 C18 21.0(3)
C2 N1 C13 C18 -168.40(16)
C5 C6 C7 C8 1.8(3)
C18 C17 C16 C15 -0.2(3)
C18 O2 C19 C21 87.52(19)
C18 O2 C19 C20 -149.70(16)
C18 C13 C14 C15 -2.5(3)
N1 C13 C14 C15 179.80(15)
C19 O2 C18 C17 -5.4(3)
C19 O2 C18 C13 173.19(15)
C16 C17 C18 O2 176.10(17)
C16 C17 C18 C13 -2.5(3)
C14 C13 C18 O2 -174.94(15)
N1 C13 C18 O2 2.7(2)
C14 C13 C18 C17 3.7(3)
N1 C13 C18 C17 -178.65(16)
C17 C16 C15 C14 1.5(3)
C13 C14 C15 C16 -0.2(3)
C10 O1 C9 C8 -5.4(3)
C10 O1 C9 C4 173.07(15)
C5 C4 C9 O1 -174.51(16)
N2 C4 C9 O1 4.1(2)
C5 C4 C9 C8 4.0(3)
N2 C4 C9 C8 -177.36(16)
C6 C7 C8 C9 -0.7(3)
O1 C9 C8 C7 176.19(17)
C4 C9 C8 C7 -2.2(3)
C9 O1 C10 C12 -151.78(16)
C9 O1 C10 C11 85.10(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659799
