#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/84/4338406.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_4338406
loop_
_publ_author_name
'Ghisolfi, Alessio'
'Waldvogel, Audrey'
'Routaboul, Lucie'
'Braunstein, Pierre'
_publ_section_title
;
 Reversible switching of the coordination modes of a
 pyridine-functionalized quinonoid zwitterion; its di- and tetranuclear
 palladium complexes.
;
_journal_issue                   11
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5515
_journal_page_last               5526
_journal_paper_doi               10.1021/ic500194y
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C20 H20 N4 O2, C H2 Cl2 '
_chemical_formula_sum            'C21 H22 Cl2 N4 O2'
_chemical_formula_weight         433.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.2959(11)
_cell_length_b                   4.51310(10)
_cell_length_c                   14.7136(5)
_cell_measurement_reflns_used    26538
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      32.032
_cell_measurement_theta_min      0.998
_cell_volume                     2078.17(11)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14730
_diffrn_reflns_theta_full        32.01
_diffrn_reflns_theta_max         32.01
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.50(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         6436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0746
_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)+(0.0965P)²+0.1869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.2020
_reflns_number_gt                4386
_reflns_number_total             6436
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic500194y_si_002.cif
_cod_data_source_block           pbag120514
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4338406--4338410.cif.
;
_cod_original_sg_symbol_Hall     'P 2c -2n '
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_database_code               4338406
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'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 0.54188(10) 0.6804(7) 0.7040(2) 0.0245(6) Uani 1 1 d .
H1 H 0.5651 0.5445 0.7052 0.029 Uiso 1 1 calc R
C2 C 0.51909(11) 0.7454(7) 0.78290(19) 0.0235(6) Uani 1 1 d .
C3 C 0.48159(11) 0.9630(7) 0.7830(2) 0.0249(6) Uani 1 1 d .
C4 C 0.47115(11) 1.0980(7) 0.7010(2) 0.0267(6) Uani 1 1 d .
H4 H 0.4477 1.2317 0.6996 0.032 Uiso 1 1 calc R
C5 C 0.49354(11) 1.0461(7) 0.6206(2) 0.0247(6) Uani 1 1 d .
C6 C 0.52990(10) 0.8197(7) 0.62292(19) 0.0221(6) Uani 1 1 d .
C7 C 0.55932(12) 0.4244(7) 0.8904(2) 0.0265(6) Uani 1 1 d .
H7A H 0.5688 0.3096 0.8368 0.032 Uiso 1 1 calc R
H7B H 0.5477 0.2835 0.9357 0.032 Uiso 1 1 calc R
C8 C 0.59761(13) 0.5892(7) 0.9315(2) 0.0317(7) Uani 1 1 d .
H8A H 0.6142 0.6844 0.8823 0.038 Uiso 1 1 calc R
H8B H 0.5872 0.7470 0.9727 0.038 Uiso 1 1 calc R
C9 C 0.62627(12) 0.3814(7) 0.9839(2) 0.0288(7) Uani 1 1 d .
C10 C 0.61285(14) 0.2719(8) 1.0688(2) 0.0353(8) Uani 1 1 d .
H10 H 0.5861 0.3295 1.0935 0.042 Uiso 1 1 calc R
C11 C 0.63913(16) 0.0798(9) 1.1154(3) 0.0431(10) Uani 1 1 d .
H11 H 0.6309 0.0045 1.1731 0.052 Uiso 1 1 calc R
C12 C 0.67756(16) -0.0013(11) 1.0772(3) 0.0488(10) Uani 1 1 d .
H12 H 0.6961 -0.1351 1.1076 0.059 Uiso 1 1 calc R
C13 C 0.68856(16) 0.1177(10) 0.9928(3) 0.0482(10) Uani 1 1 d .
H13 H 0.7152 0.0633 0.9667 0.058 Uiso 1 1 calc R
C14 C 0.58105(14) 0.5643(7) 0.5194(2) 0.0348(8) Uani 1 1 d .
H14A H 0.5694 0.4098 0.4786 0.042 Uiso 1 1 calc R
H14B H 0.5915 0.4658 0.5753 0.042 Uiso 1 1 calc R
C15 C 0.61739(14) 0.7175(8) 0.4735(3) 0.0462(10) Uani 1 1 d .
H15A H 0.6298 0.8657 0.5155 0.055 Uiso 1 1 calc R
H15B H 0.6066 0.8242 0.4194 0.055 Uiso 1 1 calc R
C16 C 0.65211(13) 0.5020(8) 0.4443(3) 0.0356(8) Uani 1 1 d .
C17 C 0.65710(15) 0.4110(9) 0.3541(3) 0.0447(10) Uani 1 1 d .
H17 H 0.6382 0.4815 0.3086 0.054 Uiso 1 1 calc R
C18 C 0.68946(16) 0.2192(10) 0.3316(3) 0.0489(11) Uani 1 1 d .
H18 H 0.6934 0.1574 0.2705 0.059 Uiso 1 1 calc R
C19 C 0.71621(15) 0.1177(9) 0.3995(3) 0.0458(10) Uani 1 1 d .
H19 H 0.7389 -0.0151 0.3864 0.055 Uiso 1 1 calc R
C20 C 0.70884(14) 0.2154(9) 0.4866(3) 0.0421(9) Uani 1 1 d .
H20 H 0.7271 0.1457 0.5335 0.051 Uiso 1 1 calc R
C21 C 0.68006(13) 0.3041(8) 0.7281(3) 0.0385(8) Uani 1 1 d .
H21A H 0.6822 0.4369 0.6747 0.046 Uiso 1 1 calc R
H21B H 0.6769 0.4288 0.7831 0.046 Uiso 1 1 calc R
N1 N 0.52604(10) 0.6316(6) 0.86339(19) 0.0273(6) Uani 1 1 d .
N2 N 0.66323(12) 0.3055(7) 0.9468(2) 0.0366(7) Uani 1 1 d .
N3 N 0.54734(10) 0.7730(6) 0.54288(19) 0.0285(6) Uani 1 1 d .
N4 N 0.67755(11) 0.4021(7) 0.5094(2) 0.0372(7) Uani 1 1 d .
O1 O 0.46342(9) 1.0064(6) 0.85750(16) 0.0365(6) Uani 1 1 d .
O2 O 0.48669(9) 1.1700(6) 0.54618(16) 0.0365(6) Uani 1 1 d .
Cl1 Cl 0.63454(4) 0.0721(2) 0.71650(7) 0.0436(2) Uani 1 1 d .
Cl2 Cl 0.72738(4) 0.0896(3) 0.73695(8) 0.0565(3) Uani 1 1 d .
H1N H 0.5073(16) 0.687(8) 0.900(3) 0.033(11) Uiso 1 1 d .
H3N H 0.5372(17) 0.872(10) 0.496(4) 0.049(13) 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.6(3)
C2 C1 H1 120.7
C6 C1 H1 120.7
N1 C2 C1 125.9(3)
N1 C2 C3 112.2(3)
C1 C2 C3 121.9(3)
O1 C3 C4 125.8(3)
O1 C3 C2 116.7(3)
C4 C3 C2 117.4(3)
C3 C4 C5 123.0(3)
C3 C4 H4 118.5
C5 C4 H4 118.5
O2 C5 C4 125.6(3)
O2 C5 C6 116.5(3)
C4 C5 C6 117.8(3)
N3 C6 C1 125.5(3)
N3 C6 C5 113.3(3)
C1 C6 C5 121.2(3)
N1 C7 C8 110.8(3)
N1 C7 H7A 109.5
C8 C7 H7A 109.5
N1 C7 H7B 109.5
C8 C7 H7B 109.5
H7A C7 H7B 108.1
C9 C8 C7 111.4(2)
C9 C8 H8A 109.4
C7 C8 H8A 109.4
C9 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
N2 C9 C10 122.4(3)
N2 C9 C8 118.0(3)
C10 C9 C8 119.6(3)
C11 C10 C9 119.0(4)
C11 C10 H10 120.5
C9 C10 H10 120.5
C12 C11 C10 119.0(4)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C13 118.4(4)
C11 C12 H12 120.8
C13 C12 H12 120.8
N2 C13 C12 123.1(4)
N2 C13 H13 118.5
C12 C13 H13 118.5
N3 C14 C15 111.1(3)
N3 C14 H14A 109.4
C15 C14 H14A 109.4
N3 C14 H14B 109.4
C15 C14 H14B 109.4
H14A C14 H14B 108.0
C14 C15 C16 112.1(3)
C14 C15 H15A 109.2
C16 C15 H15A 109.2
C14 C15 H15B 109.2
C16 C15 H15B 109.2
H15A C15 H15B 107.9
N4 C16 C17 121.3(4)
N4 C16 C15 116.3(4)
C17 C16 C15 122.4(4)
C18 C17 C16 119.8(4)
C18 C17 H17 120.1
C16 C17 H17 120.1
C17 C18 C19 118.8(4)
C17 C18 H18 120.6
C19 C18 H18 120.6
C20 C19 C18 117.8(4)
C20 C19 H19 121.1
C18 C19 H19 121.1
N4 C20 C19 124.0(4)
N4 C20 H20 118.0
C19 C20 H20 118.0
Cl2 C21 Cl1 110.8(2)
Cl2 C21 H21A 109.5
Cl1 C21 H21A 109.5
Cl2 C21 H21B 109.5
Cl1 C21 H21B 109.5
H21A C21 H21B 108.1
C2 N1 C7 128.2(3)
C2 N1 H1N 110(3)
C7 N1 H1N 121(3)
C9 N2 C13 118.1(4)
C6 N3 C14 128.1(3)
C6 N3 H3N 118(3)
C14 N3 H3N 114(3)
C16 N4 C20 118.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.394(4)
C1 C6 1.399(4)
C1 H1 0.9500
C2 N1 1.309(4)
C2 C3 1.530(5)
C3 O1 1.251(4)
C3 C4 1.391(4)
C4 C5 1.394(4)
C4 H4 0.9500
C5 O2 1.248(4)
C5 C6 1.530(4)
C6 N3 1.315(4)
C7 N1 1.455(4)
C7 C8 1.535(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.509(5)
C8 H8A 0.9900
C8 H8B 0.9900
C9 N2 1.324(5)
C9 C10 1.407(5)
C10 C11 1.378(6)
C10 H10 0.9500
C11 C12 1.377(7)
C11 H11 0.9500
C12 C13 1.396(7)
C12 H12 0.9500
C13 N2 1.344(5)
C13 H13 0.9500
C14 N3 1.456(5)
C14 C15 1.493(5)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.520(6)
C15 H15A 0.9900
C15 H15B 0.9900
C16 N4 1.325(5)
C16 C17 1.397(6)
C17 C18 1.373(7)
C17 H17 0.9500
C18 C19 1.381(7)
C18 H18 0.9500
C19 C20 1.375(6)
C19 H19 0.9500
C20 N4 1.335(5)
C20 H20 0.9500
C21 Cl2 1.774(4)
C21 Cl1 1.776(4)
C21 H21A 0.9900
C21 H21B 0.9900
N1 H1N 0.84(5)
N3 H3N 0.88(5)
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 H1N O1 0.84(5) 2.09(4) 2.590(4) 118(4) .
N1 H1N O2 0.84(5) 2.25(4) 2.862(4) 130(4) 2_675
N3 H3N O1 0.88(5) 2.11(5) 2.923(4) 153(5) 2_674
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
C6 C1 C2 N1 179.2(3)
C6 C1 C2 C3 0.1(5)
N1 C2 C3 O1 1.0(4)
C1 C2 C3 O1 -179.7(3)
N1 C2 C3 C4 -179.9(3)
C1 C2 C3 C4 -0.7(5)
O1 C3 C4 C5 178.1(3)
C2 C3 C4 C5 -0.8(5)
C3 C4 C5 O2 -176.9(3)
C3 C4 C5 C6 2.7(5)
C2 C1 C6 N3 -177.5(3)
C2 C1 C6 C5 1.9(5)
O2 C5 C6 N3 -4.2(4)
C4 C5 C6 N3 176.1(3)
O2 C5 C6 C1 176.3(3)
C4 C5 C6 C1 -3.3(5)
N1 C7 C8 C9 163.5(3)
C7 C8 C9 N2 105.8(4)
C7 C8 C9 C10 -73.3(4)
N2 C9 C10 C11 0.3(5)
C8 C9 C10 C11 179.3(3)
C9 C10 C11 C12 -0.6(6)
C10 C11 C12 C13 0.7(7)
C11 C12 C13 N2 -0.6(7)
N3 C14 C15 C16 -177.3(3)
C14 C15 C16 N4 -76.5(5)
C14 C15 C16 C17 103.1(5)
N4 C16 C17 C18 -1.4(6)
C15 C16 C17 C18 179.0(4)
C16 C17 C18 C19 0.7(6)
C17 C18 C19 C20 0.0(6)
C18 C19 C20 N4 -0.1(7)
C1 C2 N1 C7 2.6(6)
C3 C2 N1 C7 -178.2(3)
C8 C7 N1 C2 96.0(4)
C10 C9 N2 C13 -0.2(5)
C8 C9 N2 C13 -179.2(3)
C12 C13 N2 C9 0.4(6)
C1 C6 N3 C14 2.5(6)
C5 C6 N3 C14 -176.9(3)
C15 C14 N3 C6 -125.4(4)
C17 C16 N4 C20 1.3(6)
C15 C16 N4 C20 -179.1(3)
C19 C20 N4 C16 -0.5(6)
