#------------------------------------------------------------------------------
#$Date: 2017-09-01 06:16:14 +0300 (Fri, 01 Sep 2017) $
#$Revision: 200050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/40/7044068.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_7044068
loop_
_publ_author_name
'Sanz, Corey A.'
'McKay, Zach R.'
'Patrick, Brian O.'
'MacLean, Shaun W.C.'
'Hicks, Robin G.'
_publ_section_title
;
 Synthesis and redox reactions of bis(verdazyl) palladium complexes
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT02646C
_journal_year                    2017
_chemical_formula_moiety         'C13 H20 N5 O, Cl2 Pd0.5'
_chemical_formula_sum            'C13 H20 Cl2 N5 O Pd0.5'
_chemical_formula_weight         386.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2017-07-19 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.688(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3982(19)
_cell_length_b                   8.6271(12)
_cell_length_c                   14.4349(19)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.004
_cell_measurement_theta_min      2.787
_cell_volume                     1708.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.011
_diffrn_reflns_theta_min         1.484
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0539 before and 0.0416 after correction.
The Ratio of minimum to maximum transmission is 0.8749.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       irregular
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0250P)²+0.8230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4399
_reflns_number_total             4978
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt02646c2.cif
_cod_data_source_block           rh139
_cod_original_formula_sum        'C13 H20 Cl2 N5 O Pd0.50'
_cod_database_code               7044068
_shelxl_version_number           2014/6
_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_max   0.916
_shelx_estimated_absorpt_t_min   0.710
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.40430(8) 0.27241(13) 0.42681(8) 0.0188(2) Uani 1 1 d . . .
N1 N 0.37853(9) 0.25872(14) 0.57588(9) 0.0139(2) Uani 1 1 d . . .
N2 N 0.30351(9) 0.26383(14) 0.62231(9) 0.0133(2) Uani 1 1 d . . .
H2 H 0.2607 0.1897 0.5998 0.016 Uiso 1 1 d R . .
N3 N 0.24126(9) 0.48028(13) 0.51940(9) 0.0128(2) Uani 1 1 d . . .
N4 N 0.27594(9) 0.40568(14) 0.45188(9) 0.0134(2) Uani 1 1 d . . .
N5 N 0.13859(9) 0.57835(14) 0.63840(9) 0.0122(2) Uani 1 1 d . . .
H5 H 0.1260 0.6128 0.5785 0.015 Uiso 1 1 calc R . .
C1 C 0.35651(10) 0.30642(17) 0.48134(10) 0.0137(3) Uani 1 1 d . . .
C2 C 0.25362(10) 0.40638(16) 0.59954(10) 0.0119(2) Uani 1 1 d . . .
C3 C 0.45513(10) 0.14072(17) 0.61329(10) 0.0153(3) Uani 1 1 d . . .
H3 H 0.5068 0.1592 0.5813 0.018 Uiso 1 1 calc R . .
C4 C 0.50213(12) 0.1608(2) 0.72224(12) 0.0261(4) Uani 1 1 d . . .
H4A H 0.5258 0.2674 0.7359 0.039 Uiso 1 1 calc GR . .
H4B H 0.5570 0.0887 0.7449 0.039 Uiso 1 1 calc GR . .
H4C H 0.4539 0.1392 0.7561 0.039 Uiso 1 1 calc GR . .
C5 C 0.41559(12) -0.02271(18) 0.58600(13) 0.0215(3) Uani 1 1 d . . .
H5A H 0.3697 -0.0487 0.6218 0.032 Uiso 1 1 calc GR . .
H5B H 0.4697 -0.0969 0.6027 0.032 Uiso 1 1 calc GR . .
H5C H 0.3820 -0.0275 0.5160 0.032 Uiso 1 1 calc GR . .
C6 C 0.25523(11) 0.48910(17) 0.35785(11) 0.0156(3) Uani 1 1 d . . .
H6 H 0.2833 0.4270 0.3143 0.019 Uiso 1 1 calc R . .
C7 C 0.30437(12) 0.6470(2) 0.37244(13) 0.0246(3) Uani 1 1 d . . .
H7A H 0.2774 0.7108 0.4143 0.037 Uiso 1 1 calc GR . .
H7B H 0.2928 0.6981 0.3093 0.037 Uiso 1 1 calc GR . .
H7C H 0.3746 0.6340 0.4032 0.037 Uiso 1 1 calc GR . .
C8 C 0.14534(12) 0.49588(18) 0.31119(11) 0.0192(3) Uani 1 1 d . . .
H8A H 0.1183 0.3908 0.3060 0.029 Uiso 1 1 calc GR . .
H8B H 0.1306 0.5416 0.2462 0.029 Uiso 1 1 calc GR . .
H8C H 0.1163 0.5596 0.3513 0.029 Uiso 1 1 calc GR . .
C9 C 0.20853(10) 0.46930(15) 0.67007(10) 0.0115(2) Uani 1 1 d . . .
C10 C 0.08741(10) 0.63659(17) 0.69420(10) 0.0145(3) Uani 1 1 d . . .
H10 H 0.0388 0.7129 0.6687 0.017 Uiso 1 1 calc R . .
C11 C 0.10562(11) 0.58522(17) 0.78880(11) 0.0163(3) Uani 1 1 d . . .
H11 H 0.0689 0.6240 0.8285 0.020 Uiso 1 1 calc R . .
C12 C 0.17856(12) 0.47587(17) 0.82478(11) 0.0168(3) Uani 1 1 d . . .
H12 H 0.1928 0.4406 0.8900 0.020 Uiso 1 1 calc R . .
C13 C 0.23107(11) 0.41755(17) 0.76549(10) 0.0145(3) Uani 1 1 d . . .
H13 H 0.2814 0.3436 0.7900 0.017 Uiso 1 1 calc R . .
Pd1 Pd 0.0000 0.0000 0.5000 0.00983(4) Uani 1 2 d S T P
Cl1 Cl 0.16386(2) -0.05562(4) 0.56089(2) 0.01472(7) Uani 1 1 d . . .
Cl2 Cl 0.02796(3) 0.25708(4) 0.54465(3) 0.01672(7) 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 0.0000 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
N2 N1 C3 115.78(11) . .
C1 N1 N2 118.56(12) . .
C1 N1 C3 119.55(11) . .
N1 N2 H2 110.4 . .
C2 N2 N1 108.67(11) . .
C2 N2 H2 107.3 . .
C2 N3 N4 115.03(12) . .
N3 N4 C1 120.95(12) . .
N3 N4 C6 113.83(11) . .
C1 N4 C6 119.47(11) . .
C9 N5 H5 118.5 . .
C10 N5 H5 118.5 . .
C10 N5 C9 123.05(12) . .
O1 C1 N1 124.24(13) . .
O1 C1 N4 121.70(13) . .
N1 C1 N4 113.99(12) . .
N2 C2 C9 117.50(12) . .
N3 C2 N2 124.29(12) . .
N3 C2 C9 118.13(12) . .
N1 C3 H3 107.4 . .
N1 C3 C4 110.34(12) . .
N1 C3 C5 111.32(12) . .
C4 C3 H3 107.4 . .
C4 C3 C5 112.69(14) . .
C5 C3 H3 107.4 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N4 C6 H6 107.9 . .
N4 C6 C7 110.62(13) . .
N4 C6 C8 108.45(12) . .
C7 C6 H6 107.9 . .
C7 C6 C8 113.87(13) . .
C8 C6 H6 107.9 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N5 C9 C2 117.63(12) . .
N5 C9 C13 118.97(12) . .
C13 C9 C2 123.34(13) . .
N5 C10 H10 120.1 . .
N5 C10 C11 119.88(13) . .
C11 C10 H10 120.1 . .
C10 C11 H11 120.6 . .
C10 C11 C12 118.80(13) . .
C12 C11 H11 120.6 . .
C11 C12 H12 119.9 . .
C11 C12 C13 120.25(14) . .
C13 C12 H12 119.9 . .
C9 C13 C12 119.01(13) . .
C9 C13 H13 120.5 . .
C12 C13 H13 120.5 . .
Cl1 Pd1 Cl1 180.0 3_556 .
Cl1 Pd1 Cl2 91.266(13) . .
Cl1 Pd1 Cl2 91.265(13) 3_556 3_556
Cl1 Pd1 Cl2 88.734(13) 3_556 .
Cl1 Pd1 Cl2 88.735(13) . 3_556
Cl2 Pd1 Cl2 180.0 3_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2281(17) .
N1 N2 1.4344(16) .
N1 C1 1.3673(18) .
N1 C3 1.4774(18) .
N2 H2 0.8788 .
N2 C2 1.4117(18) .
N3 N4 1.3817(16) .
N3 C2 1.2850(18) .
N4 C1 1.4000(18) .
N4 C6 1.4843(18) .
N5 H5 0.8800 .
N5 C9 1.3522(18) .
N5 C10 1.3436(17) .
C2 C9 1.4677(19) .
C3 H3 1.0000 .
C3 C4 1.521(2) .
C3 C5 1.527(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6 1.0000 .
C6 C7 1.520(2) .
C6 C8 1.521(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C13 1.3894(19) .
C10 H10 0.9500 .
C10 C11 1.383(2) .
C11 H11 0.9500 .
C11 C12 1.390(2) .
C12 H12 0.9500 .
C12 C13 1.397(2) .
C13 H13 0.9500 .
Pd1 Cl1 2.3042(4) .
Pd1 Cl1 2.3041(4) 3_556
Pd1 Cl2 2.3105(5) 3_556
Pd1 Cl2 2.3106(5) .
