#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:52:35 +0100 (vie 08 de nov de 2019) $
#$Revision: 225381 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/18/7701849.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_7701849
loop_
_publ_author_name
'Nkabyo, Henry A.'
'Procacci, Barbara'
'Duckett, Simon B.'
'Koch, Klaus R.'
_publ_section_title
;
 Reversible Photo-isomerization of cis-[Pd(L-\kS,O)2] (HL = N
 N-diethyl-N’-1-naphthoylthiourea) to trans-[Pd(L-\kS,O)2] and the
 Unprecedented Formation of trans-[Pd(L-\kS,N)2] in Solution.
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C9DT03672E
_journal_year                    2019
_chemical_formula_moiety         'C32 H34 N4 O2 Pd S2'
_chemical_formula_sum            'C32 H34 N4 O2 Pd S2'
_chemical_formula_weight         677.15
_chemical_melting_point          188.0(10)
_chemical_name_systematic
trans-bis(N,N-diethyl-N?-1-naphthoylthioureato-S,N)palladium(II)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-10-22 deposited with the CCDC.	2019-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.975(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.471(3)
_cell_length_b                   7.397(2)
_cell_length_c                   15.924(5)
_cell_measurement_reflns_used    1697
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.56
_cell_volume                     1467.0(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_molecular_graphics
'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_diffrn_ambient_pressure         101.3
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8640
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         2.024
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker SMART APEX'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'symmetry-related measurement'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      1.533
_exptl_crystal_density_method    not-measured
_exptl_crystal_description       rod
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.103
_exptl_transmission_factor_max   0.892
_exptl_transmission_factor_min   0.811
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0326P)²+0.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2744
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03672e2.cif
_cod_data_source_block           C_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '187-189' was changed to
'188.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1467.1(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7701849
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.921
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Pd1 Pd 0.500000 0.000000 0.500000 0.01042(9) Uani 1 2 d S . P
S1 S 0.37075(5) -0.22640(10) 0.48816(5) 0.01409(16) Uani 1 1 d . . .
N1 N 0.39708(17) 0.0262(3) 0.59557(15) 0.0125(5) Uani 1 1 d . . .
O1 O 0.39584(16) -0.0249(3) 0.73773(13) 0.0217(5) Uani 1 1 d . . .
C12 C 0.3258(2) -0.1084(4) 0.57419(17) 0.0134(6) Uani 1 1 d . . .
C5 C 0.6245(2) 0.4014(4) 0.78284(18) 0.0161(6) Uani 1 1 d . . .
C11 C 0.4258(2) 0.0651(4) 0.67875(18) 0.0144(6) Uani 1 1 d . . .
N2 N 0.23311(17) -0.1393(3) 0.60785(15) 0.0156(5) Uani 1 1 d . . .
C4 C 0.5967(2) 0.5574(4) 0.7348(2) 0.0191(7) Uani 1 1 d . . .
H4 H 0.629501 0.667153 0.748526 0.023 Uiso 1 1 calc R U .
C1 C 0.4936(2) 0.2300(4) 0.69485(17) 0.0129(6) Uani 1 1 d . . .
C9 C 0.6045(2) 0.0817(4) 0.81243(19) 0.0188(6) Uani 1 1 d . . .
H9 H 0.571926 -0.029444 0.801326 0.023 Uiso 1 1 calc R U .
C10 C 0.5721(2) 0.2349(4) 0.76332(18) 0.0139(6) Uani 1 1 d . . .
C6 C 0.7044(2) 0.4086(5) 0.84955(19) 0.0218(7) Uani 1 1 d . . .
H6 H 0.738489 0.517849 0.862201 0.026 Uiso 1 1 calc R U .
C13 C 0.1668(2) -0.2970(4) 0.58003(19) 0.0191(7) Uani 1 1 d . . .
H13A H 0.136799 -0.353067 0.628611 0.023 Uiso 1 1 calc R U .
H13B H 0.212077 -0.385479 0.554121 0.023 Uiso 1 1 calc R U .
C2 C 0.4719(2) 0.3845(4) 0.64845(18) 0.0164(6) Uani 1 1 d . . .
H2 H 0.422657 0.379539 0.602620 0.020 Uiso 1 1 calc R U .
C8 C 0.6826(2) 0.0948(5) 0.8756(2) 0.0241(7) Uani 1 1 d . . .
H8 H 0.703118 -0.007993 0.905950 0.029 Uiso 1 1 calc R U .
C15 C 0.1800(2) -0.0114(4) 0.6647(2) 0.0238(7) Uani 1 1 d . . .
H15A H 0.222943 -0.001597 0.717016 0.029 Uiso 1 1 calc R U .
H15B H 0.110384 -0.059454 0.677512 0.029 Uiso 1 1 calc R U .
C3 C 0.5230(2) 0.5494(4) 0.6692(2) 0.0195(7) Uani 1 1 d . . .
H3 H 0.506186 0.652706 0.637939 0.023 Uiso 1 1 calc R U .
C14 C 0.0766(2) -0.2427(4) 0.5179(2) 0.0260(7) Uani 1 1 d . . .
H14A H 0.027930 -0.163815 0.544949 0.039 Uiso 1 1 calc R U .
H14B H 0.038808 -0.348721 0.498049 0.039 Uiso 1 1 calc R U .
H14C H 0.105795 -0.180990 0.471178 0.039 Uiso 1 1 calc R U .
C7 C 0.7321(2) 0.2595(5) 0.8952(2) 0.0263(8) Uani 1 1 d . . .
H7 H 0.783711 0.267054 0.939357 0.032 Uiso 1 1 calc R U .
C16 C 0.1652(2) 0.1746(4) 0.6267(2) 0.0305(8) Uani 1 1 d . . .
H16A H 0.234186 0.229610 0.620954 0.046 Uiso 1 1 calc R U .
H16B H 0.123541 0.247698 0.662633 0.046 Uiso 1 1 calc R U .
H16C H 0.128619 0.164602 0.572364 0.046 Uiso 1 1 calc R U .
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'
Pd Pd -0.9988 1.0072 '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'
S S 0.1246 0.1234 '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
N1 Pd1 N1 180.0 . 3_656
N1 Pd1 S1 70.74(6) . .
N1 Pd1 S1 109.26(6) 3_656 .
N1 Pd1 S1 109.26(6) . 3_656
N1 Pd1 S1 70.74(6) 3_656 3_656
S1 Pd1 S1 180.0 . 3_656
C12 S1 Pd1 79.95(9) . .
C12 N1 C11 121.5(2) . .
C12 N1 Pd1 99.84(17) . .
C11 N1 Pd1 126.08(18) . .
N2 C12 N1 126.7(3) . .
N2 C12 S1 123.9(2) . .
N1 C12 S1 109.21(19) . .
C4 C5 C6 121.1(3) . .
C4 C5 C10 119.4(3) . .
C6 C5 C10 119.6(3) . .
O1 C11 N1 123.1(3) . .
O1 C11 C1 120.2(3) . .
N1 C11 C1 116.6(2) . .
C12 N2 C13 120.1(2) . .
C12 N2 C15 124.3(2) . .
C13 N2 C15 115.0(2) . .
C3 C4 C5 121.1(3) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C2 C1 C10 119.7(3) . .
C2 C1 C11 119.3(2) . .
C10 C1 C11 120.6(2) . .
C8 C9 C10 121.3(3) . .
C8 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C5 C10 C9 117.1(3) . .
C5 C10 C1 118.6(3) . .
C9 C10 C1 124.3(3) . .
C7 C6 C5 121.3(3) . .
C7 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
N2 C13 C14 111.7(2) . .
N2 C13 H13A 109.3 . .
C14 C13 H13A 109.3 . .
N2 C13 H13B 109.3 . .
C14 C13 H13B 109.3 . .
H13A C13 H13B 107.9 . .
C1 C2 C3 121.2(3) . .
C1 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C9 C8 C7 121.2(3) . .
C9 C8 H8 119.4 . .
C7 C8 H8 119.4 . .
N2 C15 C16 112.6(3) . .
N2 C15 H15A 109.1 . .
C16 C15 H15A 109.1 . .
N2 C15 H15B 109.1 . .
C16 C15 H15B 109.1 . .
H15A C15 H15B 107.8 . .
C4 C3 C2 119.9(3) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C6 C7 C8 119.6(3) . .
C6 C7 H7 120.2 . .
C8 C7 H7 120.2 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.050(2) .
Pd1 N1 2.050(2) 3_656
Pd1 S1 2.3253(8) .
Pd1 S1 2.3253(8) 3_656
S1 C12 1.742(3) .
N1 C12 1.366(3) .
N1 C11 1.384(4) .
O1 C11 1.225(3) .
C12 N2 1.319(3) .
C5 C4 1.418(4) .
C5 C6 1.419(4) .
C5 C10 1.421(4) .
C11 C1 1.499(4) .
N2 C13 1.484(3) .
N2 C15 1.488(4) .
C4 C3 1.357(4) .
C4 H4 0.9300 .
C1 C2 1.380(4) .
C1 C10 1.428(4) .
C9 C8 1.366(4) .
C9 C10 1.423(4) .
C9 H9 0.9300 .
C6 C7 1.356(4) .
C6 H6 0.9300 .
C13 C14 1.514(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C2 C3 1.407(4) .
C2 H2 0.9300 .
C8 C7 1.394(4) .
C8 H8 0.9300 .
C15 C16 1.510(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C3 H3 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C7 H7 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
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
C13 H13A O1 0.97 2.53 3.480(4) 166.3 2_546
C15 H15A O1 0.97 2.17 2.878(4) 128.6 .
C16 H16A N1 0.96 2.58 3.156(4) 119.0 .
C16 H16B O1 0.96 2.33 3.218(4) 152.9 2_556
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
C11 N1 C12 N2 45.7(4)
Pd1 N1 C12 N2 -170.4(3)
C11 N1 C12 S1 -138.9(2)
Pd1 N1 C12 S1 4.94(19)
Pd1 S1 C12 N2 171.1(3)
Pd1 S1 C12 N1 -4.36(17)
C12 N1 C11 O1 5.3(4)
Pd1 N1 C11 O1 -128.7(2)
C12 N1 C11 C1 -172.5(2)
Pd1 N1 C11 C1 53.5(3)
N1 C12 N2 C13 -177.2(3)
S1 C12 N2 C13 8.1(4)
N1 C12 N2 C15 12.1(5)
S1 C12 N2 C15 -162.6(2)
C6 C5 C4 C3 177.7(3)
C10 C5 C4 C3 -1.8(4)
O1 C11 C1 C2 -137.4(3)
N1 C11 C1 C2 40.4(4)
O1 C11 C1 C10 35.8(4)
N1 C11 C1 C10 -146.4(3)
C4 C5 C10 C9 178.8(2)
C6 C5 C10 C9 -0.7(4)
C4 C5 C10 C1 0.8(4)
C6 C5 C10 C1 -178.7(3)
C8 C9 C10 C5 0.0(4)
C8 C9 C10 C1 178.0(3)
C2 C1 C10 C5 1.3(4)
C11 C1 C10 C5 -171.9(2)
C2 C1 C10 C9 -176.7(3)
C11 C1 C10 C9 10.2(4)
C4 C5 C6 C7 -179.4(3)
C10 C5 C6 C7 0.1(4)
C12 N2 C13 C14 -100.0(3)
C15 N2 C13 C14 71.5(3)
C10 C1 C2 C3 -2.4(4)
C11 C1 C2 C3 170.9(2)
C10 C9 C8 C7 1.2(5)
C12 N2 C15 C16 54.1(4)
C13 N2 C15 C16 -117.0(3)
C5 C4 C3 C2 0.7(4)
C1 C2 C3 C4 1.4(4)
C5 C6 C7 C8 1.1(5)
C9 C8 C7 C6 -1.8(5)
