#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/20/7222012.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_7222012
loop_
_publ_author_name
'ARUMUGAM, VIGNESH'
'Kaminsky, Werner'
'Nallasamy, Dharmaraj'
_publ_section_title
;
 ONO Pincer type Pd(II) complexes: Synthesis, crystal structure and
 catalytic activity towards C-2 arylation of quinoline scaffolds
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA15342E
_journal_year                    2015
_chemical_formula_moiety         'C36 H27 N2 O3 P Pd'
_chemical_formula_sum            'C36 H27 N2 O3 P Pd'
_chemical_formula_weight         672.97
_chemical_name_common            pdsnah
_chemical_name_systematic
;
 pdsnah
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2014-10-23T13:30:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-02-06 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.079(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8683(4)
_cell_length_b                   21.5484(10)
_cell_length_c                   15.2026(7)
_cell_measurement_reflns_used    713
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     2888.8(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'maXus, Zortep'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1187
_diffrn_reflns_av_unetI/netI     0.1656
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12436
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.32
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.8663
_exptl_absorpt_correction_T_min  0.7564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL2008
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.35
_refine_diff_density_min         -1.764
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.131
_reflns_number_gt                4183
_reflns_number_total             7108
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ra15342e2.cif
_cod_data_source_block           pdsnah2
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7222012
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -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
C1 C 1.2725(4) 0.4472(2) 0.6689(3) 0.0186(10) Uani 1 1 d .
C2 C 1.4049(5) 0.4609(2) 0.6276(3) 0.0273(11) Uani 1 1 d .
H2 H 1.4287 0.5028 0.6158 0.033 Uiso 1 1 calc R
C3 C 1.4992(5) 0.4144(3) 0.6046(3) 0.0292(12) Uani 1 1 d .
H3 H 1.5871 0.4249 0.577 0.035 Uiso 1 1 calc R
C4 C 1.4691(5) 0.3531(2) 0.6206(3) 0.0260(12) Uani 1 1 d .
H4 H 1.536 0.3216 0.6048 0.031 Uiso 1 1 calc R
C5 C 1.3403(4) 0.3380(2) 0.6599(3) 0.0244(11) Uani 1 1 d .
H5 H 1.3191 0.2955 0.6704 0.029 Uiso 1 1 calc R
C6 C 1.2395(4) 0.3840(2) 0.6848(3) 0.0195(10) Uani 1 1 d .
C7 C 1.1101(4) 0.3620(2) 0.7258(3) 0.0208(10) Uani 1 1 d .
H7 H 1.104 0.3189 0.7381 0.025 Uiso 1 1 calc R
C8 C 0.7816(4) 0.4152(2) 0.7998(3) 0.0189(10) Uani 1 1 d .
C9 C 0.6408(4) 0.3959(2) 0.8379(3) 0.0172(10) Uani 1 1 d .
C10 C 0.5953(4) 0.3326(2) 0.8435(3) 0.0186(10) Uani 1 1 d .
C11 C 0.4631(4) 0.3181(2) 0.8785(3) 0.0194(10) Uani 1 1 d .
H11 H 0.4338 0.2759 0.8823 0.023 Uiso 1 1 calc R
C12 C 0.3694(4) 0.3651(2) 0.9091(3) 0.0161(9) Uani 1 1 d .
C13 C 0.2276(4) 0.3522(2) 0.9435(3) 0.0189(10) Uani 1 1 d .
H13 H 0.1912 0.3108 0.9444 0.023 Uiso 1 1 calc R
C14 C 0.1461(5) 0.3987(2) 0.9745(3) 0.0229(11) Uani 1 1 d .
H14 H 0.0524 0.3892 0.9964 0.027 Uiso 1 1 calc R
C15 C 0.1958(5) 0.4611(2) 0.9754(3) 0.0250(11) Uani 1 1 d .
H15 H 0.1385 0.4929 0.9996 0.03 Uiso 1 1 calc R
C16 C 0.3283(4) 0.4747(2) 0.9405(3) 0.0186(10) Uani 1 1 d .
H16 H 0.3617 0.5165 0.9395 0.022 Uiso 1 1 calc R
C17 C 0.4157(4) 0.4277(2) 0.9062(3) 0.0176(10) Uani 1 1 d .
C18 C 0.5509(4) 0.4417(2) 0.8679(3) 0.0207(10) Uani 1 1 d .
H18 H 0.5803 0.4838 0.8629 0.025 Uiso 1 1 calc R
C19 C 1.0187(4) 0.6254(2) 0.6169(3) 0.0192(10) Uani 1 1 d .
C20 C 1.0447(4) 0.5845(2) 0.5484(3) 0.0216(10) Uani 1 1 d .
H20 H 1.0245 0.5415 0.554 0.026 Uiso 1 1 calc R
C21 C 1.1000(5) 0.6068(3) 0.4723(3) 0.0278(12) Uani 1 1 d .
H21 H 1.1178 0.579 0.426 0.033 Uiso 1 1 calc R
C22 C 1.1290(5) 0.6696(3) 0.4640(3) 0.0279(12) Uani 1 1 d .
H22 H 1.1655 0.685 0.4115 0.033 Uiso 1 1 calc R
C23 C 1.1054(5) 0.7097(2) 0.5312(3) 0.0282(11) Uani 1 1 d .
H23 H 1.1266 0.7527 0.5255 0.034 Uiso 1 1 calc R
C24 C 1.0505(5) 0.6877(2) 0.6074(3) 0.0234(11) Uani 1 1 d .
H24 H 1.0345 0.7158 0.6536 0.028 Uiso 1 1 calc R
C25 C 1.0338(4) 0.6388(2) 0.8073(3) 0.0149(9) Uani 1 1 d .
C26 C 1.1594(4) 0.6119(2) 0.8576(3) 0.0192(10) Uani 1 1 d .
H26 H 1.1971 0.5727 0.8415 0.023 Uiso 1 1 calc R
C27 C 1.2276(4) 0.6435(2) 0.9312(3) 0.0209(11) Uani 1 1 d .
H27 H 1.3122 0.6256 0.9657 0.025 Uiso 1 1 calc R
C28 C 1.1734(5) 0.7003(2) 0.9543(3) 0.0221(11) Uani 1 1 d .
H28 H 1.2204 0.7213 1.0049 0.026 Uiso 1 1 calc R
C29 C 1.0511(5) 0.7273(2) 0.9045(3) 0.0257(11) Uani 1 1 d .
H29 H 1.0153 0.7669 0.9204 0.031 Uiso 1 1 calc R
C30 C 0.9809(5) 0.6963(2) 0.8314(3) 0.0236(11) Uani 1 1 d .
H30 H 0.8962 0.7146 0.7975 0.028 Uiso 1 1 calc R
C31 C 0.7493(4) 0.6118(2) 0.7072(3) 0.0190(10) Uani 1 1 d .
C32 C 0.6642(5) 0.6261(2) 0.6281(3) 0.0244(11) Uani 1 1 d .
H32 H 0.7117 0.6274 0.575 0.029 Uiso 1 1 calc R
C33 C 0.5090(4) 0.6386(2) 0.6257(3) 0.0273(12) Uani 1 1 d .
H33 H 0.4515 0.6489 0.5713 0.033 Uiso 1 1 calc R
C34 C 0.4396(5) 0.6358(2) 0.7035(3) 0.0292(12) Uani 1 1 d .
H34 H 0.3342 0.6441 0.7024 0.035 Uiso 1 1 calc R
C35 C 0.5244(5) 0.6209(2) 0.7829(3) 0.0268(12) Uani 1 1 d .
H35 H 0.4766 0.6189 0.8359 0.032 Uiso 1 1 calc R
C36 C 0.6768(4) 0.6090(2) 0.7852(3) 0.0233(11) Uani 1 1 d .
H36 H 0.7339 0.5989 0.8398 0.028 Uiso 1 1 calc R
N1 N 1.0027(3) 0.39732(18) 0.7468(2) 0.0165(8) Uani 1 1 d .
N2 N 0.8769(3) 0.37126(18) 0.7820(2) 0.0185(8) Uani 1 1 d .
O1 O 1.1913(3) 0.49613(15) 0.68758(18) 0.0197(7) Uani 1 1 d .
O2 O 0.7986(3) 0.47407(15) 0.78571(18) 0.0202(7) Uani 1 1 d .
O3 O 0.6805(3) 0.28585(15) 0.8147(2) 0.0231(7) Uani 1 1 d .
H3O H 0.7564 0.3008 0.7936 0.035 Uiso 1 1 calc R
P1 P 0.94908(12) 0.59293(6) 0.71508(7) 0.0163(3) Uani 1 1 d .
Pd1 Pd 0.99202(3) 0.489152(18) 0.73396(2) 0.01591(11) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O1 C1 C6 127.0(4)
O1 C1 C2 115.0(4)
C6 C1 C2 118.0(4)
C3 C2 C1 121.0(5)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 121.4(4)
C2 C3 H3 119.3
C4 C3 H3 119.3
C3 C4 C5 119.2(4)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 121.6(5)
C4 C5 H5 119.2
C6 C5 H5 119.2
C5 C6 C1 118.7(4)
C5 C6 C7 116.1(4)
C1 C6 C7 125.2(4)
N1 C7 C6 123.9(5)
N1 C7 H7 118.1
C6 C7 H7 118.1
O2 C8 N2 125.4(4)
O2 C8 C9 117.0(4)
N2 C8 C9 117.6(4)
C18 C9 C10 119.2(4)
C18 C9 C8 117.9(4)
C10 C9 C8 122.9(4)
O3 C10 C11 118.9(4)
O3 C10 C9 121.2(3)
C11 C10 C9 119.9(4)
C10 C11 C12 121.3(4)
C10 C11 H11 119.4
C12 C11 H11 119.4
C17 C12 C11 119.3(4)
C17 C12 C13 117.6(4)
C11 C12 C13 123.1(4)
C14 C13 C12 120.3(4)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 122.1(4)
C13 C14 H14 118.9
C15 C14 H14 118.9
C16 C15 C14 118.5(4)
C16 C15 H15 120.7
C14 C15 H15 120.7
C15 C16 C17 121.2(4)
C15 C16 H16 119.4
C17 C16 H16 119.4
C16 C17 C12 120.2(4)
C16 C17 C18 121.4(4)
C12 C17 C18 118.4(4)
C9 C18 C17 121.9(4)
C9 C18 H18 119.1
C17 C18 H18 119.1
C24 C19 C20 118.8(4)
C24 C19 P1 123.5(3)
C20 C19 P1 117.7(4)
C21 C20 C19 120.1(5)
C21 C20 H20 119.9
C19 C20 H20 119.9
C22 C21 C20 119.9(4)
C22 C21 H21 120.1
C20 C21 H21 120.1
C23 C22 C21 120.2(4)
C23 C22 H22 119.9
C21 C22 H22 119.9
C22 C23 C24 120.1(5)
C22 C23 H23 119.9
C24 C23 H23 119.9
C19 C24 C23 120.9(4)
C19 C24 H24 119.5
C23 C24 H24 119.5
C30 C25 C26 119.7(4)
C30 C25 P1 124.5(3)
C26 C25 P1 115.8(3)
C27 C26 C25 119.1(4)
C27 C26 H26 120.5
C25 C26 H26 120.5
C28 C27 C26 120.5(4)
C28 C27 H27 119.8
C26 C27 H27 119.8
C27 C28 C29 120.7(4)
C27 C28 H28 119.7
C29 C28 H28 119.7
C28 C29 C30 119.8(4)
C28 C29 H29 120.1
C30 C29 H29 120.1
C29 C30 C25 120.3(4)
C29 C30 H30 119.8
C25 C30 H30 119.8
C32 C31 C36 119.0(4)
C32 C31 P1 123.2(3)
C36 C31 P1 117.7(3)
C31 C32 C33 120.7(4)
C31 C32 H32 119.6
C33 C32 H32 119.6
C34 C33 C32 119.4(4)
C34 C33 H33 120.3
C32 C33 H33 120.3
C35 C34 C33 120.0(4)
C35 C34 H34 120
C33 C34 H34 120
C36 C35 C34 120.4(4)
C36 C35 H35 119.8
C34 C35 H35 119.8
C35 C36 C31 120.4(4)
C35 C36 H36 119.8
C31 C36 H36 119.8
C7 N1 N2 119.8(4)
C7 N1 Pd1 126.4(3)
N2 N1 Pd1 113.8(2)
C8 N2 N1 110.2(4)
C1 O1 Pd1 122.9(3)
C8 O2 Pd1 110.2(3)
C10 O3 H3O 109.5
C31 P1 C25 104.56(19)
C31 P1 C19 105.93(19)
C25 P1 C19 106.07(19)
C31 P1 Pd1 112.23(15)
C25 P1 Pd1 112.75(15)
C19 P1 Pd1 114.51(15)
O1 Pd1 O2 174.30(13)
O1 Pd1 N1 94.33(12)
O2 Pd1 N1 80.37(12)
O1 Pd1 P1 91.38(10)
O2 Pd1 P1 94.05(10)
N1 Pd1 P1 173.09(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.325(5)
C1 C6 1.418(6)
C1 C2 1.421(6)
C2 C3 1.373(6)
C2 H2 0.95
C3 C4 1.374(7)
C3 H3 0.95
C4 C5 1.384(6)
C4 H4 0.95
C5 C6 1.414(6)
C5 H5 0.95
C6 C7 1.442(6)
C7 N1 1.285(5)
C7 H7 0.95
C8 O2 1.299(5)
C8 N2 1.316(5)
C8 C9 1.490(5)
C9 C18 1.376(6)
C9 C10 1.427(6)
C10 O3 1.359(5)
C10 C11 1.374(5)
C11 C12 1.418(6)
C11 H11 0.95
C12 C17 1.412(6)
C12 C13 1.440(5)
C13 C14 1.349(6)
C13 H13 0.95
C14 C15 1.414(7)
C14 H14 0.95
C15 C16 1.370(6)
C15 H15 0.95
C16 C17 1.408(6)
C16 H16 0.95
C17 C18 1.420(5)
C18 H18 0.95
C19 C24 1.381(6)
C19 C20 1.403(6)
C19 P1 1.815(4)
C20 C21 1.389(6)
C20 H20 0.95
C21 C22 1.388(7)
C21 H21 0.95
C22 C23 1.371(7)
C22 H22 0.95
C23 C24 1.387(6)
C23 H23 0.95
C24 H24 0.95
C25 C30 1.389(6)
C25 C26 1.407(6)
C25 P1 1.812(4)
C26 C27 1.393(6)
C26 H26 0.95
C27 C28 1.374(6)
C27 H27 0.95
C28 C29 1.383(6)
C28 H28 0.95
C29 C30 1.386(6)
C29 H29 0.95
C30 H30 0.95
C31 C32 1.384(6)
C31 C36 1.410(6)
C31 P1 1.809(4)
C32 C33 1.399(6)
C32 H32 0.95
C33 C34 1.392(6)
C33 H33 0.95
C34 C35 1.391(6)
C34 H34 0.95
C35 C36 1.372(6)
C35 H35 0.95
C36 H36 0.95
N1 N2 1.404(4)
N1 Pd1 1.990(4)
O1 Pd1 1.976(2)
O2 Pd1 1.988(3)
O3 H3O 0.84
P1 Pd1 2.2814(13)
