# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
#TrackingRef '- pdH2LCl2_miyake.cif'

_publ_contact_author_name        'Prof. Hiroyuki Miyake'
_publ_contact_author_address     
;
Department of Chemistry
Graduate School of Science
Osaka City University
3-3-138 Sugimoto, Sumiyoshi-ku,
Osaka 558-8585, Japan
;

_publ_section_title              
;
Helicity Inversion from Left- to Right-Handed Square Planar Pd(II) Complexes:
Synthesis of a Diastereomer Pair from a Single Chiral Ligand and their
Structure Dynamism
;
_publ_contact_author_email       miyake@sci.osaka-cu.ac.jp
loop_
_publ_author_name
'Hiroyuki Miyake'
'Masashi Ueda'
'Saori Murota'
'Hideki Sugimoto'
'Hiroshi Tsukube'

data_[Pd(H2L)Cl2]
_database_code_depnum_ccdc_archive 'CCDC 861130'
#TrackingRef '- pdH2LCl2_miyake.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C12 H26 Cl2 N4 O2 Pd'
_chemical_formula_sum            'C12 H26 Cl2 N4 O2 Pd'
_chemical_formula_weight         435.67

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 212121'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.2009(10)
_cell_length_b                   12.1922(15)
_cell_length_c                   13.7244(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1706.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8818
_cell_measurement_theta_min      4.1673
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.409
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_T_max  0.8164
_exptl_absorpt_process_details   '(Jacobson, 1998)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       \w
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_reflns_number            17076
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.17
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3883
_reflns_number_gt                3827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SIR97(Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.6678P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(19)
_refine_ls_number_reflns         3883
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0449
_refine_ls_wR_factor_gt          0.0447
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration rmad

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.923632(14) 0.087851(13) 0.604048(11) 0.00838(5) Uani 1 1 d . . .
C1 C 0.4662(2) 0.2522(2) 0.73731(18) 0.0190(5) Uani 1 1 d . . .
H1 H 0.4938 0.2129 0.7961 0.029 Uiso 1 1 calc R . .
H2 H 0.3702 0.2523 0.7333 0.029 Uiso 1 1 calc R . .
H3 H 0.4981 0.3280 0.7401 0.029 Uiso 1 1 calc R . .
N1 N 0.51977(19) 0.19848(17) 0.65251(15) 0.0169(4) Uani 1 1 d . . .
H4 H 0.4927 0.2198 0.5947 0.020 Uiso 1 1 calc R . .
C2 C 0.6091(2) 0.11737(18) 0.65742(17) 0.0132(5) Uani 1 1 d . . .
O1 O 0.66148(15) 0.08789(16) 0.73351(11) 0.0181(3) Uani 1 1 d . . .
C3 C 0.6312(2) 0.06122(18) 0.55839(17) 0.0127(5) Uani 1 1 d . . .
H5 H 0.6326 0.1199 0.5075 0.015 Uiso 1 1 calc R . .
C4 C 0.5128(2) -0.0130(2) 0.53733(19) 0.0180(5) Uani 1 1 d . . .
H6 H 0.5297 -0.0563 0.4785 0.027 Uiso 1 1 calc R . .
H7 H 0.4346 0.0324 0.5274 0.027 Uiso 1 1 calc R . .
H8 H 0.4985 -0.0624 0.5926 0.027 Uiso 1 1 calc R . .
N2 N 0.76055(17) 0.00242(15) 0.55396(13) 0.0103(4) Uani 1 1 d . . .
C5 C 0.7907(2) -0.02219(19) 0.44949(16) 0.0143(4) Uani 1 1 d . . .
H9 H 0.7247 -0.0727 0.4235 0.021 Uiso 1 1 calc R . .
H10 H 0.8776 -0.0560 0.4448 0.021 Uiso 1 1 calc R . .
H11 H 0.7896 0.0461 0.4118 0.021 Uiso 1 1 calc R . .
C6 C 0.75605(19) -0.10123(17) 0.61321(17) 0.0130(4) Uani 1 1 d . . .
H12 H 0.6974 -0.1550 0.5812 0.016 Uiso 1 1 calc R . .
H13 H 0.7202 -0.0851 0.6787 0.016 Uiso 1 1 calc R . .
C7 C 0.8913(2) -0.14922(18) 0.62290(17) 0.0131(5) Uani 1 1 d . . .
H14 H 0.8894 -0.2111 0.6696 0.016 Uiso 1 1 calc R . .
H15 H 0.9205 -0.1779 0.5590 0.016 Uiso 1 1 calc R . .
N3 N 0.98619(17) -0.06356(15) 0.65792(13) 0.0109(4) Uani 1 1 d . . .
C8 C 0.9757(2) -0.0508(2) 0.76588(16) 0.0147(5) Uani 1 1 d . . .
H16 H 0.8864 -0.0282 0.7830 0.022 Uiso 1 1 calc R . .
H17 H 1.0381 0.0050 0.7880 0.022 Uiso 1 1 calc R . .
H18 H 0.9957 -0.1210 0.7975 0.022 Uiso 1 1 calc R . .
C9 C 1.1250(2) -0.0938(2) 0.62970(15) 0.0131(4) Uani 1 1 d . . .
H19 H 1.1852 -0.0359 0.6553 0.016 Uiso 1 1 calc R . .
C10 C 1.1696(2) -0.2044(2) 0.67038(19) 0.0192(5) Uani 1 1 d . . .
H20 H 1.1646 -0.2029 0.7417 0.029 Uiso 1 1 calc R . .
H21 H 1.2602 -0.2186 0.6502 0.029 Uiso 1 1 calc R . .
H22 H 1.1125 -0.2626 0.6453 0.029 Uiso 1 1 calc R . .
C11 C 1.1359(2) -0.0951(2) 0.51734(16) 0.0141(4) Uani 1 1 d . . .
O2 O 1.11698(17) -0.17951(14) 0.47065(13) 0.0200(4) Uani 1 1 d . . .
N4 N 1.16653(19) -0.00045(17) 0.47455(14) 0.0155(4) Uani 1 1 d . . .
H23 H 1.1840 0.0575 0.5105 0.019 Uiso 1 1 calc R . .
C12 C 1.1713(2) 0.0082(2) 0.36861(17) 0.0209(5) Uani 1 1 d . . .
H24 H 1.2281 -0.0496 0.3424 0.031 Uiso 1 1 calc R . .
H25 H 1.2063 0.0801 0.3502 0.031 Uiso 1 1 calc R . .
H26 H 1.0827 -0.0003 0.3420 0.031 Uiso 1 1 calc R . .
Cl1 Cl 1.11402(5) 0.17298(5) 0.65683(4) 0.01515(12) Uani 1 1 d . . .
Cl2 Cl 0.84778(5) 0.25255(4) 0.54450(4) 0.01436(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pd1 0.00917(7) 0.00739(7) 0.00858(7) -0.00043(7) 0.00015(6) -0.00016(6)
C1 0.0186(11) 0.0210(13) 0.0175(12) -0.0044(11) 0.0030(8) 0.0044(9)
N1 0.0183(10) 0.0215(11) 0.0109(10) -0.0007(8) 0.0007(7) 0.0071(8)
C2 0.0106(10) 0.0133(11) 0.0158(11) 0.0015(9) 0.0017(8) -0.0016(7)
O1 0.0211(8) 0.0207(8) 0.0125(8) -0.0017(8) -0.0041(6) 0.0038(8)
C3 0.0104(10) 0.0133(12) 0.0145(11) 0.0009(9) -0.0029(8) 0.0003(8)
C4 0.0118(11) 0.0205(13) 0.0217(12) -0.0029(11) -0.0035(9) -0.0016(9)
N2 0.0110(9) 0.0103(9) 0.0095(9) -0.0006(7) -0.0002(7) -0.0005(7)
C5 0.0155(11) 0.0177(12) 0.0097(11) -0.0018(9) 0.0010(8) 0.0011(8)
C6 0.0143(10) 0.0097(10) 0.0149(11) 0.0008(10) 0.0010(8) -0.0021(8)
C7 0.0160(11) 0.0084(10) 0.0150(12) 0.0002(9) -0.0019(8) -0.0017(8)
N3 0.0133(8) 0.0096(10) 0.0098(9) -0.0002(7) -0.0007(7) 0.0019(7)
C8 0.0211(11) 0.0154(11) 0.0077(11) 0.0014(9) -0.0002(8) 0.0020(9)
C9 0.0130(9) 0.0120(10) 0.0143(11) -0.0022(10) -0.0019(7) 0.0027(9)
C10 0.0201(12) 0.0180(12) 0.0193(13) 0.0003(10) -0.0030(9) 0.0070(9)
C11 0.0108(9) 0.0158(11) 0.0156(11) -0.0011(10) -0.0010(8) 0.0034(9)
O2 0.0300(10) 0.0140(8) 0.0161(9) -0.0040(7) 0.0017(7) 0.0007(7)
N4 0.0170(10) 0.0153(10) 0.0142(10) -0.0022(8) 0.0032(8) -0.0019(8)
C12 0.0253(13) 0.0213(13) 0.0160(13) -0.0006(10) 0.0059(9) -0.0054(10)
Cl1 0.0124(3) 0.0130(3) 0.0200(3) -0.0046(2) -0.00075(18) -0.00242(19)
Cl2 0.0166(3) 0.0102(2) 0.0163(3) 0.0035(2) 0.00146(19) 0.00141(19)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 N2 2.0797(18) . ?
Pd1 N3 2.0885(18) . ?
Pd1 Cl2 2.3019(6) . ?
Pd1 Cl1 2.3182(5) . ?
C1 N1 1.443(3) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
N1 C2 1.346(3) . ?
N1 H4 0.8800 . ?
C2 O1 1.227(3) . ?
C2 C3 1.538(3) . ?
C3 N2 1.503(3) . ?
C3 C4 1.537(3) . ?
C3 H5 1.0000 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
N2 C6 1.503(3) . ?
N2 C5 1.497(3) . ?
C5 H9 0.9800 . ?
C5 H10 0.9800 . ?
C5 H11 0.9800 . ?
C6 C7 1.505(3) . ?
C6 H12 0.9900 . ?
C6 H13 0.9900 . ?
C7 N3 1.503(3) . ?
C7 H14 0.9900 . ?
C7 H15 0.9900 . ?
N3 C8 1.494(3) . ?
N3 C9 1.514(3) . ?
C8 H16 0.9800 . ?
C8 H17 0.9800 . ?
C8 H18 0.9800 . ?
C9 C10 1.528(3) . ?
C9 C11 1.546(3) . ?
C9 H19 1.0000 . ?
C10 H20 0.9800 . ?
C10 H21 0.9800 . ?
C10 H22 0.9800 . ?
C11 O2 1.228(3) . ?
C11 N4 1.332(3) . ?
N4 C12 1.459(3) . ?
N4 H23 0.8800 . ?
C12 H24 0.9800 . ?
C12 H25 0.9800 . ?
C12 H26 0.9800 . ?

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
_geom_angle_publ_flag
N2 Pd1 N3 85.34(7) . . ?
N2 Pd1 Cl2 92.90(5) . . ?
N3 Pd1 Cl2 178.12(5) . . ?
N2 Pd1 Cl1 176.12(5) . . ?
N3 Pd1 Cl1 91.67(5) . . ?
Cl2 Pd1 Cl1 90.11(2) . . ?
N1 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 N1 C1 123.3(2) . . ?
C2 N1 H4 118.3 . . ?
C1 N1 H4 118.3 . . ?
O1 C2 N1 123.5(2) . . ?
O1 C2 C3 123.88(19) . . ?
N1 C2 C3 112.47(19) . . ?
N2 C3 C4 113.69(18) . . ?
N2 C3 C2 112.15(17) . . ?
C4 C3 C2 108.21(18) . . ?
N2 C3 H5 107.5 . . ?
C4 C3 H5 107.5 . . ?
C2 C3 H5 107.5 . . ?
C3 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
C3 C4 H8 109.5 . . ?
H6 C4 H8 109.5 . . ?
H7 C4 H8 109.5 . . ?
C3 N2 C6 110.63(16) . . ?
C3 N2 C5 108.35(17) . . ?
C6 N2 C5 110.85(17) . . ?
C3 N2 Pd1 116.74(13) . . ?
C6 N2 Pd1 105.46(13) . . ?
C5 N2 Pd1 104.63(13) . . ?
N2 C5 H9 109.5 . . ?
N2 C5 H10 109.5 . . ?
H9 C5 H10 109.5 . . ?
N2 C5 H11 109.5 . . ?
H9 C5 H11 109.5 . . ?
H10 C5 H11 109.5 . . ?
N2 C6 C7 110.29(17) . . ?
N2 C6 H12 109.6 . . ?
C7 C6 H12 109.6 . . ?
N2 C6 H13 109.6 . . ?
C7 C6 H13 109.6 . . ?
H12 C6 H13 108.1 . . ?
N3 C7 C6 110.41(17) . . ?
N3 C7 H14 109.6 . . ?
C6 C7 H14 109.6 . . ?
N3 C7 H15 109.6 . . ?
C6 C7 H15 109.6 . . ?
H14 C7 H15 108.1 . . ?
C8 N3 C7 110.07(17) . . ?
C8 N3 C9 110.25(16) . . ?
C7 N3 C9 110.57(17) . . ?
C8 N3 Pd1 103.74(13) . . ?
C7 N3 Pd1 107.71(13) . . ?
C9 N3 Pd1 114.25(14) . . ?
N3 C8 H16 109.5 . . ?
N3 C8 H17 109.5 . . ?
H16 C8 H17 109.5 . . ?
N3 C8 H18 109.5 . . ?
H16 C8 H18 109.5 . . ?
H17 C8 H18 109.5 . . ?
N3 C9 C10 113.58(19) . . ?
N3 C9 C11 108.97(16) . . ?
C10 C9 C11 109.5(2) . . ?
N3 C9 H19 108.2 . . ?
C10 C9 H19 108.2 . . ?
C11 C9 H19 108.2 . . ?
C9 C10 H20 109.5 . . ?
C9 C10 H21 109.5 . . ?
H20 C10 H21 109.5 . . ?
C9 C10 H22 109.5 . . ?
H20 C10 H22 109.5 . . ?
H21 C10 H22 109.5 . . ?
O2 C11 N4 122.2(2) . . ?
O2 C11 C9 121.2(2) . . ?
N4 C11 C9 116.6(2) . . ?
C11 N4 C12 120.6(2) . . ?
C11 N4 H23 119.7 . . ?
C12 N4 H23 119.7 . . ?
N4 C12 H24 109.5 . . ?
N4 C12 H25 109.5 . . ?
H24 C12 H25 109.5 . . ?
N4 C12 H26 109.5 . . ?
H24 C12 H26 109.5 . . ?
H25 C12 H26 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C2 O1 -6.4(4) . . . . ?
C1 N1 C2 C3 169.9(2) . . . . ?
O1 C2 C3 N2 -24.8(3) . . . . ?
N1 C2 C3 N2 158.89(18) . . . . ?
O1 C2 C3 C4 101.4(2) . . . . ?
N1 C2 C3 C4 -74.9(2) . . . . ?
C4 C3 N2 C6 -49.3(2) . . . . ?
C2 C3 N2 C6 73.8(2) . . . . ?
C4 C3 N2 C5 72.4(2) . . . . ?
C2 C3 N2 C5 -164.45(17) . . . . ?
C4 C3 N2 Pd1 -169.90(15) . . . . ?
C2 C3 N2 Pd1 -46.7(2) . . . . ?
N3 Pd1 N2 C3 143.15(15) . . . . ?
Cl2 Pd1 N2 C3 -36.20(15) . . . . ?
N3 Pd1 N2 C6 19.87(13) . . . . ?
Cl2 Pd1 N2 C6 -159.48(12) . . . . ?
N3 Pd1 N2 C5 -97.13(14) . . . . ?
Cl2 Pd1 N2 C5 83.53(13) . . . . ?
C3 N2 C6 C7 -170.15(17) . . . . ?
C5 N2 C6 C7 69.6(2) . . . . ?
Pd1 N2 C6 C7 -43.07(19) . . . . ?
N2 C6 C7 N3 51.1(2) . . . . ?
C6 C7 N3 C8 81.0(2) . . . . ?
C6 C7 N3 C9 -156.97(18) . . . . ?
C6 C7 N3 Pd1 -31.5(2) . . . . ?
N2 Pd1 N3 C8 -110.68(13) . . . . ?
Cl1 Pd1 N3 C8 71.80(12) . . . . ?
N2 Pd1 N3 C7 6.00(14) . . . . ?
Cl1 Pd1 N3 C7 -171.53(13) . . . . ?
N2 Pd1 N3 C9 129.26(14) . . . . ?
Cl1 Pd1 N3 C9 -48.27(13) . . . . ?
C8 N3 C9 C10 63.2(2) . . . . ?
C7 N3 C9 C10 -58.8(2) . . . . ?
Pd1 N3 C9 C10 179.54(15) . . . . ?
C8 N3 C9 C11 -174.44(19) . . . . ?
C7 N3 C9 C11 63.6(2) . . . . ?
Pd1 N3 C9 C11 -58.1(2) . . . . ?
N3 C9 C11 O2 -91.6(3) . . . . ?
C10 C9 C11 O2 33.2(3) . . . . ?
N3 C9 C11 N4 88.3(2) . . . . ?
C10 C9 C11 N4 -146.9(2) . . . . ?
O2 C11 N4 C12 3.6(3) . . . . ?
C9 C11 N4 C12 -176.26(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.060

data_[Pd(HL)Cl]
_database_code_depnum_ccdc_archive 'CCDC 861131'
#TrackingRef '- pdHLCl_miyake.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C12 H25 Cl N4 O2 Pd'
_chemical_formula_sum            'C12 H25 Cl N4 O2 Pd'
_chemical_formula_weight         399.21

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0991(10)
_cell_length_b                   14.147(2)
_cell_length_c                   15.733(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1580.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7624
_cell_measurement_theta_min      4.0673
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6493
_exptl_absorpt_correction_T_max  0.8768
_exptl_absorpt_process_details   '(Jacobson, 1998)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       \w
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_reflns_number            15637
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3592
_reflns_number_gt                3519
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SIR97(Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0191P)^2^+1.5997P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_number_reflns         3592
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0545
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration rmad

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.31784(2) 0.995641(13) 0.752776(12) 0.00979(6) Uani 1 1 d . . .
C1 C 0.0629(4) 1.1311(2) 0.85584(18) 0.0163(6) Uani 1 1 d . . .
H1 H -0.0715 1.1288 0.8700 0.024 Uiso 1 1 calc R . .
H2 H 0.0810 1.1690 0.8043 0.024 Uiso 1 1 calc R . .
H3 H 0.1326 1.1598 0.9030 0.024 Uiso 1 1 calc R . .
N1 N 0.1323(3) 1.03528(16) 0.84125(15) 0.0129(5) Uani 1 1 d . . .
C2 C 0.0488(4) 0.9637(2) 0.88032(16) 0.0134(5) Uani 1 1 d . . .
O1 O -0.0878(3) 0.96803(15) 0.93075(12) 0.0185(5) Uani 1 1 d . . .
C3 C 0.1225(4) 0.8659(2) 0.85566(17) 0.0128(6) Uani 1 1 d . . .
H4 H 0.0474 0.8446 0.8054 0.015 Uiso 1 1 calc R . .
C4 C 0.0962(5) 0.7919(2) 0.92459(18) 0.0185(6) Uani 1 1 d . . .
H5 H 0.1577 0.7330 0.9073 0.028 Uiso 1 1 calc R . .
H6 H -0.0386 0.7805 0.9333 0.028 Uiso 1 1 calc R . .
H7 H 0.1526 0.8146 0.9777 0.028 Uiso 1 1 calc R . .
N2 N 0.3225(3) 0.87750(16) 0.82605(14) 0.0119(4) Uani 1 1 d . . .
C5 C 0.4561(5) 0.8862(2) 0.89938(18) 0.0183(6) Uani 1 1 d . . .
H8 H 0.4712 0.8243 0.9266 0.027 Uiso 1 1 calc R . .
H9 H 0.4058 0.9315 0.9407 0.027 Uiso 1 1 calc R . .
H10 H 0.5786 0.9083 0.8788 0.027 Uiso 1 1 calc R . .
C6 C 0.3831(4) 0.80068(19) 0.76654(18) 0.0165(6) Uani 1 1 d . . .
H11 H 0.2781 0.7841 0.7279 0.020 Uiso 1 1 calc R . .
H12 H 0.4178 0.7435 0.7993 0.020 Uiso 1 1 calc R . .
C7 C 0.5500(4) 0.8344(2) 0.71559(18) 0.0155(6) Uani 1 1 d . . .
H13 H 0.5870 0.7851 0.6741 0.019 Uiso 1 1 calc R . .
H14 H 0.6581 0.8459 0.7540 0.019 Uiso 1 1 calc R . .
N3 N 0.5008(3) 0.92432(16) 0.66918(14) 0.0109(5) Uani 1 1 d . . .
C8 C 0.3877(4) 0.9011(2) 0.59206(17) 0.0175(6) Uani 1 1 d . . .
H15 H 0.3546 0.9596 0.5622 0.026 Uiso 1 1 calc R . .
H16 H 0.2723 0.8681 0.6090 0.026 Uiso 1 1 calc R . .
H17 H 0.4617 0.8605 0.5543 0.026 Uiso 1 1 calc R . .
C9 C 0.6742(4) 0.97914(19) 0.64307(16) 0.0127(5) Uani 1 1 d . . .
H18 H 0.6355 1.0265 0.5992 0.015 Uiso 1 1 calc R . .
C10 C 0.7583(4) 1.0324(2) 0.71742(18) 0.0168(6) Uani 1 1 d . . .
H19 H 0.6666 1.0784 0.7388 0.025 Uiso 1 1 calc R . .
H20 H 0.8723 1.0656 0.6988 0.025 Uiso 1 1 calc R . .
H21 H 0.7905 0.9878 0.7628 0.025 Uiso 1 1 calc R . .
C11 C 0.8241(4) 0.9140(2) 0.60289(17) 0.0146(5) Uani 1 1 d . . .
O2 O 0.9335(3) 0.86749(16) 0.64739(13) 0.0182(4) Uani 1 1 d . . .
N4 N 0.8271(4) 0.91422(18) 0.51778(14) 0.0162(5) Uani 1 1 d . . .
H22 H 0.7457 0.9497 0.4902 0.019 Uiso 1 1 calc R . .
C12 C 0.9600(5) 0.8580(2) 0.46965(19) 0.0223(7) Uani 1 1 d . . .
H23 H 1.0640 0.8983 0.4504 0.033 Uiso 1 1 calc R . .
H24 H 0.8964 0.8304 0.4202 0.033 Uiso 1 1 calc R . .
H25 H 1.0096 0.8073 0.5057 0.033 Uiso 1 1 calc R . .
Cl1 Cl 0.28770(10) 1.12666(5) 0.66518(4) 0.01659(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pd1 0.00835(9) 0.01027(9) 0.01074(8) 0.00028(9) -0.00003(8) 0.00064(7)
C1 0.0169(15) 0.0140(14) 0.0180(14) -0.0020(11) 0.0001(12) 0.0031(12)
N1 0.0117(11) 0.0137(11) 0.0132(10) -0.0026(8) -0.0003(9) 0.0018(9)
C2 0.0119(13) 0.0173(14) 0.0109(12) -0.0011(10) -0.0028(11) 0.0011(11)
O1 0.0166(10) 0.0231(11) 0.0157(9) -0.0010(8) 0.0056(8) 0.0012(9)
C3 0.0104(13) 0.0161(14) 0.0120(12) 0.0000(10) 0.0007(10) -0.0003(11)
C4 0.0189(15) 0.0199(16) 0.0168(13) 0.0044(11) 0.0030(12) -0.0004(13)
N2 0.0105(11) 0.0106(11) 0.0147(10) 0.0022(8) -0.0006(10) -0.0004(10)
C5 0.0160(15) 0.0219(16) 0.0172(13) 0.0037(11) -0.0062(13) -0.0023(13)
C6 0.0176(14) 0.0095(12) 0.0225(15) -0.0006(10) 0.0045(12) 0.0021(10)
C7 0.0131(14) 0.0121(13) 0.0212(13) 0.0012(10) 0.0028(12) 0.0028(12)
N3 0.0089(11) 0.0123(11) 0.0115(10) -0.0012(9) 0.0000(9) -0.0003(9)
C8 0.0129(14) 0.0245(17) 0.0151(13) -0.0075(11) 0.0002(12) -0.0026(12)
C9 0.0084(11) 0.0153(13) 0.0143(11) 0.0019(9) -0.0007(10) 0.0005(11)
C10 0.0129(13) 0.0190(15) 0.0184(12) 0.0001(10) -0.0009(11) -0.0006(11)
C11 0.0118(13) 0.0151(14) 0.0168(12) 0.0031(10) 0.0015(12) -0.0028(12)
O2 0.0114(10) 0.0238(11) 0.0194(10) 0.0042(8) -0.0008(9) 0.0048(9)
N4 0.0133(12) 0.0229(13) 0.0123(10) -0.0001(9) -0.0004(10) 0.0048(11)
C12 0.0217(16) 0.0250(17) 0.0202(14) -0.0012(12) 0.0042(13) 0.0060(14)
Cl1 0.0169(3) 0.0152(3) 0.0176(3) 0.0047(2) 0.0000(3) 0.0017(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 N1 1.997(2) . ?
Pd1 N2 2.031(2) . ?
Pd1 N3 2.106(2) . ?
Pd1 Cl1 2.3196(7) . ?
C1 N1 1.460(4) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
N1 C2 1.324(4) . ?
C2 O1 1.255(3) . ?
C2 C3 1.529(4) . ?
C3 N2 1.503(4) . ?
C3 C4 1.519(4) . ?
C3 H4 1.0000 . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
N2 C6 1.498(3) . ?
N2 C5 1.498(4) . ?
C5 H8 0.9800 . ?
C5 H9 0.9800 . ?
C5 H10 0.9800 . ?
C6 C7 1.508(4) . ?
C6 H11 0.9900 . ?
C6 H12 0.9900 . ?
C7 N3 1.508(3) . ?
C7 H13 0.9900 . ?
C7 H14 0.9900 . ?
N3 C8 1.491(3) . ?
N3 C9 1.512(3) . ?
C8 H15 0.9800 . ?
C8 H16 0.9800 . ?
C8 H17 0.9800 . ?
C9 C10 1.515(4) . ?
C9 C11 1.544(4) . ?
C9 H18 1.0000 . ?
C10 H19 0.9800 . ?
C10 H20 0.9800 . ?
C10 H21 0.9800 . ?
C11 O2 1.235(3) . ?
C11 N4 1.339(3) . ?
N4 C12 1.448(4) . ?
N4 H22 0.8800 . ?
C12 H23 0.9800 . ?
C12 H24 0.9800 . ?
C12 H25 0.9800 . ?

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
_geom_angle_publ_flag
N1 Pd1 N2 81.15(9) . . ?
N1 Pd1 N3 167.63(9) . . ?
N2 Pd1 N3 87.14(9) . . ?
N1 Pd1 Cl1 97.41(7) . . ?
N2 Pd1 Cl1 175.20(7) . . ?
N3 Pd1 Cl1 93.94(7) . . ?
N1 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 N1 C1 119.1(2) . . ?
C2 N1 Pd1 113.82(18) . . ?
C1 N1 Pd1 126.35(19) . . ?
O1 C2 N1 127.0(3) . . ?
O1 C2 C3 118.0(2) . . ?
N1 C2 C3 114.9(2) . . ?
N2 C3 C4 114.3(2) . . ?
N2 C3 C2 107.7(2) . . ?
C4 C3 C2 113.6(2) . . ?
N2 C3 H4 106.9 . . ?
C4 C3 H4 106.9 . . ?
C2 C3 H4 106.9 . . ?
C3 C4 H5 109.5 . . ?
C3 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
C6 N2 C5 111.0(2) . . ?
C6 N2 C3 112.7(2) . . ?
C5 N2 C3 111.6(2) . . ?
C6 N2 Pd1 104.31(15) . . ?
C5 N2 Pd1 112.35(18) . . ?
C3 N2 Pd1 104.47(16) . . ?
N2 C5 H8 109.5 . . ?
N2 C5 H9 109.5 . . ?
H8 C5 H9 109.5 . . ?
N2 C5 H10 109.5 . . ?
H8 C5 H10 109.5 . . ?
H9 C5 H10 109.5 . . ?
N2 C6 C7 109.2(2) . . ?
N2 C6 H11 109.8 . . ?
C7 C6 H11 109.8 . . ?
N2 C6 H12 109.8 . . ?
C7 C6 H12 109.8 . . ?
H11 C6 H12 108.3 . . ?
C6 C7 N3 110.0(2) . . ?
C6 C7 H13 109.7 . . ?
N3 C7 H13 109.7 . . ?
C6 C7 H14 109.7 . . ?
N3 C7 H14 109.7 . . ?
H13 C7 H14 108.2 . . ?
C8 N3 C7 109.5(2) . . ?
C8 N3 C9 109.3(2) . . ?
C7 N3 C9 112.1(2) . . ?
C8 N3 Pd1 106.35(17) . . ?
C7 N3 Pd1 104.17(16) . . ?
C9 N3 Pd1 115.21(16) . . ?
N3 C8 H15 109.5 . . ?
N3 C8 H16 109.5 . . ?
H15 C8 H16 109.5 . . ?
N3 C8 H17 109.5 . . ?
H15 C8 H17 109.5 . . ?
H16 C8 H17 109.5 . . ?
N3 C9 C10 111.5(2) . . ?
N3 C9 C11 111.5(2) . . ?
C10 C9 C11 110.0(2) . . ?
N3 C9 H18 107.9 . . ?
C10 C9 H18 107.9 . . ?
C11 C9 H18 107.9 . . ?
C9 C10 H19 109.5 . . ?
C9 C10 H20 109.5 . . ?
H19 C10 H20 109.5 . . ?
C9 C10 H21 109.5 . . ?
H19 C10 H21 109.5 . . ?
H20 C10 H21 109.5 . . ?
O2 C11 N4 123.9(3) . . ?
O2 C11 C9 121.3(2) . . ?
N4 C11 C9 114.8(2) . . ?
C11 N4 C12 122.1(3) . . ?
C11 N4 H22 118.9 . . ?
C12 N4 H22 118.9 . . ?
N4 C12 H23 109.5 . . ?
N4 C12 H24 109.5 . . ?
H23 C12 H24 109.5 . . ?
N4 C12 H25 109.5 . . ?
H23 C12 H25 109.5 . . ?
H24 C12 H25 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Pd1 N1 C2 -24.38(19) . . . . ?
N3 Pd1 N1 C2 -5.3(5) . . . . ?
Cl1 Pd1 N1 C2 151.00(18) . . . . ?
N2 Pd1 N1 C1 165.8(2) . . . . ?
N3 Pd1 N1 C1 -175.2(4) . . . . ?
Cl1 Pd1 N1 C1 -18.9(2) . . . . ?
C1 N1 C2 O1 -0.3(4) . . . . ?
Pd1 N1 C2 O1 -171.0(2) . . . . ?
C1 N1 C2 C3 175.6(2) . . . . ?
Pd1 N1 C2 C3 5.0(3) . . . . ?
O1 C2 C3 N2 -157.7(2) . . . . ?
N1 C2 C3 N2 26.0(3) . . . . ?
O1 C2 C3 C4 -30.0(4) . . . . ?
N1 C2 C3 C4 153.6(2) . . . . ?
C4 C3 N2 C6 77.8(3) . . . . ?
C2 C3 N2 C6 -155.0(2) . . . . ?
C4 C3 N2 C5 -47.9(3) . . . . ?
C2 C3 N2 C5 79.3(3) . . . . ?
C4 C3 N2 Pd1 -169.58(19) . . . . ?
C2 C3 N2 Pd1 -42.3(2) . . . . ?
N1 Pd1 N2 C6 154.89(18) . . . . ?
N3 Pd1 N2 C6 -21.09(17) . . . . ?
N1 Pd1 N2 C5 -84.74(19) . . . . ?
N3 Pd1 N2 C5 99.27(19) . . . . ?
N1 Pd1 N2 C3 36.39(16) . . . . ?
N3 Pd1 N2 C3 -139.59(16) . . . . ?
C5 N2 C6 C7 -74.8(3) . . . . ?
C3 N2 C6 C7 159.2(2) . . . . ?
Pd1 N2 C6 C7 46.5(2) . . . . ?
N2 C6 C7 N3 -56.6(3) . . . . ?
C6 C7 N3 C8 -78.7(3) . . . . ?
C6 C7 N3 C9 159.9(2) . . . . ?
C6 C7 N3 Pd1 34.7(2) . . . . ?
N1 Pd1 N3 C8 89.6(5) . . . . ?
N2 Pd1 N3 C8 108.49(19) . . . . ?
Cl1 Pd1 N3 C8 -66.83(18) . . . . ?
N1 Pd1 N3 C7 -26.0(5) . . . . ?
N2 Pd1 N3 C7 -7.11(17) . . . . ?
Cl1 Pd1 N3 C7 177.57(16) . . . . ?
N1 Pd1 N3 C9 -149.1(4) . . . . ?
N2 Pd1 N3 C9 -130.30(18) . . . . ?
Cl1 Pd1 N3 C9 54.39(17) . . . . ?
C8 N3 C9 C10 160.7(2) . . . . ?
C7 N3 C9 C10 -77.7(3) . . . . ?
Pd1 N3 C9 C10 41.1(3) . . . . ?
C8 N3 C9 C11 -75.9(3) . . . . ?
C7 N3 C9 C11 45.6(3) . . . . ?
Pd1 N3 C9 C11 164.50(16) . . . . ?
N3 C9 C11 O2 -82.4(3) . . . . ?
C10 C9 C11 O2 41.8(3) . . . . ?
N3 C9 C11 N4 99.0(3) . . . . ?
C10 C9 C11 N4 -136.7(3) . . . . ?
O2 C11 N4 C12 0.8(5) . . . . ?
C9 C11 N4 C12 179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.070