# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2007

data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440

_publ_contact_author_name        'Fu Fu'
_publ_contact_author_address     
;
Organometallic Photochemistry
Technical Institute of Physica and Chemistry, Chginese Academy of
Sciences
zhong guan cun bei 1 tiao 2, CAS
Beijing
China
100080
COLUMBIA
;

_publ_contact_author_email       'WF FU@YAHOO.COM.CN'

_publ_section_title              
;
Conformation Impact on Photophysical Properties of
Bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine and Its Zinc(II) Complex
;
loop_
_publ_author_name
'Fu Fu'
'Yong Chen'
'Jun-Li Li'
'Xue-Mei Ou'
'Xi-Juan Zhao'

data_51009d
_database_code_depnum_ccdc_archive 'CCDC 635917'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N5'
_chemical_formula_weight         329.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   12.921(2)
_cell_length_b                   8.1511(15)
_cell_length_c                   16.069(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.767(3)
_cell_angle_gamma                90.00
_cell_volume                     1680.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3548
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      26.37

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.823774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            9133
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.40
_reflns_number_total             3441
_reflns_number_gt                2442
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0627P)^2^+0.5281P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3441
_refine_ls_number_parameters     234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
N1 N 1.17346(10) 1.36665(18) 0.33757(9) 0.0393(3) Uani 1 1 d . . .
N2 N 1.12500(10) 1.11817(17) 0.27767(9) 0.0374(3) Uani 1 1 d . . .
N3 N 1.09202(11) 0.86880(18) 0.21709(10) 0.0428(4) Uani 1 1 d D . .
N4 N 0.94002(10) 0.73679(17) 0.15635(9) 0.0392(3) Uani 1 1 d . . .
N5 N 0.79062(10) 0.61655(18) 0.09220(9) 0.0424(4) Uani 1 1 d . . .
C1 C 1.23490(16) 1.6238(3) 0.39975(14) 0.0573(5) Uani 1 1 d . . .
H1A H 1.2400 1.6346 0.4596 0.086 Uiso 1 1 calc R . .
H1B H 1.2211 1.7292 0.3742 0.086 Uiso 1 1 calc R . .
H1C H 1.2993 1.5816 0.3843 0.086 Uiso 1 1 calc R . .
C2 C 1.14776(14) 1.5080(2) 0.37031(11) 0.0429(4) Uani 1 1 d . . .
C3 C 1.04395(15) 1.5539(2) 0.37681(13) 0.0526(5) Uani 1 1 d . . .
H3 H 1.0303 1.6545 0.4006 0.063 Uiso 1 1 calc R . .
C4 C 0.96294(14) 1.4529(2) 0.34873(13) 0.0484(5) Uani 1 1 d . . .
C5 C 0.85076(17) 1.5034(3) 0.35156(18) 0.0766(8) Uani 1 1 d . . .
H5A H 0.8487 1.6048 0.3817 0.115 Uiso 1 1 calc R . .
H5B H 0.8152 1.4198 0.3793 0.115 Uiso 1 1 calc R . .
H5C H 0.8172 1.5176 0.2955 0.115 Uiso 1 1 calc R . .
C6 C 0.98803(13) 1.2992(2) 0.31515(11) 0.0402(4) Uani 1 1 d . . .
C7 C 0.91408(13) 1.1795(2) 0.28514(12) 0.0485(5) Uani 1 1 d . . .
H7 H 0.8436 1.1993 0.2874 0.058 Uiso 1 1 calc R . .
C8 C 0.94434(14) 1.0361(2) 0.25302(12) 0.0484(5) Uani 1 1 d . . .
H8 H 0.8956 0.9568 0.2337 0.058 Uiso 1 1 calc R . .
C9 C 1.05240(12) 1.0100(2) 0.24963(10) 0.0371(4) Uani 1 1 d . . .
C10 C 1.09429(12) 1.2613(2) 0.31045(10) 0.0350(4) Uani 1 1 d . . .
C11 C 1.04149(12) 0.7338(2) 0.17800(10) 0.0363(4) Uani 1 1 d . . .
C12 C 1.10660(12) 0.5993(2) 0.16259(11) 0.0399(4) Uani 1 1 d . . .
H12 H 1.1782 0.6038 0.1779 0.048 Uiso 1 1 calc R . .
C13 C 1.06142(13) 0.4648(2) 0.12508(11) 0.0395(4) Uani 1 1 d . . .
H13 H 1.1022 0.3744 0.1153 0.047 Uiso 1 1 calc R . .
C14 C 0.95244(12) 0.4602(2) 0.10051(10) 0.0345(4) Uani 1 1 d . . .
C15 C 0.89897(13) 0.3258(2) 0.05939(11) 0.0404(4) Uani 1 1 d . . .
C16 C 0.95458(17) 0.1712(2) 0.04021(14) 0.0558(5) Uani 1 1 d . . .
H16A H 0.9063 0.0974 0.0096 0.084 Uiso 1 1 calc R . .
H16B H 0.9834 0.1202 0.0916 0.084 Uiso 1 1 calc R . .
H16C H 1.0096 0.1970 0.0072 0.084 Uiso 1 1 calc R . .
C17 C 0.79446(14) 0.3442(2) 0.03559(12) 0.0452(4) Uani 1 1 d . . .
H17 H 0.7569 0.2587 0.0082 0.054 Uiso 1 1 calc R . .
C18 C 0.74320(13) 0.4900(2) 0.05191(11) 0.0437(4) Uani 1 1 d . . .
C19 C 0.62907(15) 0.5081(3) 0.02157(15) 0.0630(6) Uani 1 1 d . . .
H19A H 0.6067 0.6171 0.0333 0.094 Uiso 1 1 calc R . .
H19B H 0.5899 0.4300 0.0498 0.094 Uiso 1 1 calc R . .
H19C H 0.6178 0.4888 -0.0377 0.094 Uiso 1 1 calc R . .
C20 C 0.89496(12) 0.6019(2) 0.11662(10) 0.0356(4) Uani 1 1 d . . .
H3A H 1.1618(8) 0.870(2) 0.2179(12) 0.048(5) Uiso 1 1 d 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
N1 0.0328(7) 0.0394(8) 0.0441(8) -0.0008(7) -0.0023(6) -0.0026(6)
N2 0.0290(7) 0.0379(8) 0.0438(8) -0.0001(6) -0.0019(6) -0.0016(6)
N3 0.0273(7) 0.0409(8) 0.0588(10) -0.0070(7) -0.0012(6) -0.0018(6)
N4 0.0297(7) 0.0375(8) 0.0489(8) -0.0039(7) -0.0013(6) 0.0011(6)
N5 0.0280(7) 0.0459(9) 0.0521(9) -0.0058(7) -0.0006(6) 0.0002(6)
C1 0.0479(11) 0.0514(12) 0.0715(14) -0.0157(10) 0.0025(10) -0.0086(9)
C2 0.0425(10) 0.0404(10) 0.0456(10) -0.0031(8) 0.0037(7) -0.0041(8)
C3 0.0477(11) 0.0453(11) 0.0665(13) -0.0139(10) 0.0136(9) -0.0036(9)
C4 0.0378(10) 0.0495(11) 0.0596(12) -0.0059(9) 0.0130(8) -0.0002(8)
C5 0.0443(12) 0.0662(15) 0.123(2) -0.0250(15) 0.0260(13) 0.0030(10)
C6 0.0337(8) 0.0444(10) 0.0430(10) -0.0010(8) 0.0071(7) -0.0024(7)
C7 0.0285(8) 0.0574(12) 0.0607(12) -0.0098(10) 0.0103(8) -0.0040(8)
C8 0.0319(9) 0.0528(11) 0.0610(12) -0.0125(9) 0.0076(8) -0.0103(8)
C9 0.0317(8) 0.0403(9) 0.0386(9) 0.0004(7) 0.0008(6) -0.0023(7)
C10 0.0308(8) 0.0384(9) 0.0350(8) 0.0034(7) 0.0004(6) -0.0016(7)
C11 0.0309(8) 0.0368(9) 0.0401(9) 0.0010(7) 0.0002(6) -0.0015(7)
C12 0.0269(8) 0.0449(10) 0.0466(10) 0.0023(8) -0.0016(7) 0.0027(7)
C13 0.0343(8) 0.0391(9) 0.0447(9) 0.0011(8) 0.0028(7) 0.0072(7)
C14 0.0349(8) 0.0354(9) 0.0331(8) 0.0026(7) 0.0042(6) 0.0006(7)
C15 0.0437(10) 0.0383(9) 0.0392(9) -0.0005(7) 0.0053(7) -0.0013(7)
C16 0.0614(13) 0.0435(11) 0.0619(12) -0.0103(10) 0.0042(10) 0.0045(9)
C17 0.0440(10) 0.0440(10) 0.0466(10) -0.0062(8) 0.0019(8) -0.0107(8)
C18 0.0324(9) 0.0522(11) 0.0456(10) -0.0036(9) 0.0009(7) -0.0066(8)
C19 0.0343(10) 0.0729(15) 0.0785(15) -0.0122(12) -0.0066(9) -0.0059(10)
C20 0.0299(8) 0.0377(9) 0.0387(9) -0.0003(7) 0.0020(6) -0.0011(7)

_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
N1 C2 1.325(2) . ?
N1 C10 1.367(2) . ?
N2 C9 1.327(2) . ?
N2 C10 1.358(2) . ?
N3 C9 1.387(2) . ?
N3 C11 1.391(2) . ?
N3 H3A 0.900(9) . ?
N4 C11 1.317(2) . ?
N4 C20 1.367(2) . ?
N5 C18 1.328(2) . ?
N5 C20 1.364(2) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.408(3) . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.416(3) . ?
C4 C5 1.513(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.410(2) . ?
C6 C10 1.418(2) . ?
C7 C8 1.354(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.420(2) . ?
C8 H8 0.9300 . ?
C11 C12 1.421(2) . ?
C12 C13 1.350(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.417(2) . ?
C13 H13 0.9300 . ?
C14 C20 1.413(2) . ?
C14 C15 1.417(2) . ?
C15 C17 1.368(2) . ?
C15 C16 1.500(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.401(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.505(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C2 N1 C10 117.37(15) . . ?
C9 N2 C10 118.38(14) . . ?
C9 N3 C11 130.72(14) . . ?
C9 N3 H3A 113.4(12) . . ?
C11 N3 H3A 115.7(12) . . ?
C11 N4 C20 117.69(14) . . ?
C18 N5 C20 117.11(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 123.07(16) . . ?
N1 C2 C1 117.25(16) . . ?
C3 C2 C1 119.67(17) . . ?
C4 C3 C2 121.00(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C6 117.25(17) . . ?
C3 C4 C5 121.71(18) . . ?
C6 C4 C5 121.03(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 124.46(16) . . ?
C7 C6 C10 116.88(16) . . ?
C4 C6 C10 118.67(15) . . ?
C8 C7 C6 120.88(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 118.27(16) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
N2 C9 N3 113.70(14) . . ?
N2 C9 C8 123.12(16) . . ?
N3 C9 C8 123.18(15) . . ?
N2 C10 N1 114.92(14) . . ?
N2 C10 C6 122.47(15) . . ?
N1 C10 C6 122.60(15) . . ?
N4 C11 N3 120.30(15) . . ?
N4 C11 C12 124.03(15) . . ?
N3 C11 C12 115.66(14) . . ?
C13 C12 C11 118.06(15) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 120.59(16) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C20 C14 C15 118.65(15) . . ?
C20 C14 C13 116.99(15) . . ?
C15 C14 C13 124.34(15) . . ?
C17 C15 C14 117.17(16) . . ?
C17 C15 C16 121.04(17) . . ?
C14 C15 C16 121.77(16) . . ?
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 . . ?
C15 C17 C18 120.92(16) . . ?
C15 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
N5 C18 C17 123.30(16) . . ?
N5 C18 C19 117.39(17) . . ?
C17 C18 C19 119.30(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 C20 N4 114.57(14) . . ?
N5 C20 C14 122.81(15) . . ?
N4 C20 C14 122.60(14) . . ?

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
C10 N1 C2 C3 -1.1(3) . . . . ?
C10 N1 C2 C1 -179.78(16) . . . . ?
N1 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 178.42(19) . . . . ?
C2 C3 C4 C6 1.7(3) . . . . ?
C2 C3 C4 C5 -177.1(2) . . . . ?
C3 C4 C6 C7 178.63(19) . . . . ?
C5 C4 C6 C7 -2.5(3) . . . . ?
C3 C4 C6 C10 -1.7(3) . . . . ?
C5 C4 C6 C10 177.09(19) . . . . ?
C4 C6 C7 C8 179.23(19) . . . . ?
C10 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C10 N2 C9 N3 179.66(14) . . . . ?
C10 N2 C9 C8 -0.6(3) . . . . ?
C11 N3 C9 N2 -175.81(17) . . . . ?
C11 N3 C9 C8 4.5(3) . . . . ?
C7 C8 C9 N2 1.1(3) . . . . ?
C7 C8 C9 N3 -179.17(17) . . . . ?
C9 N2 C10 N1 -179.67(14) . . . . ?
C9 N2 C10 C6 -0.5(2) . . . . ?
C2 N1 C10 N2 -179.84(15) . . . . ?
C2 N1 C10 C6 0.9(2) . . . . ?
C7 C6 C10 N2 1.0(3) . . . . ?
C4 C6 C10 N2 -178.70(16) . . . . ?
C7 C6 C10 N1 -179.87(16) . . . . ?
C4 C6 C10 N1 0.5(3) . . . . ?
C20 N4 C11 N3 178.71(15) . . . . ?
C20 N4 C11 C12 0.0(2) . . . . ?
C9 N3 C11 N4 9.6(3) . . . . ?
C9 N3 C11 C12 -171.55(17) . . . . ?
N4 C11 C12 C13 -1.5(3) . . . . ?
N3 C11 C12 C13 179.73(16) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C20 0.4(2) . . . . ?
C12 C13 C14 C15 178.69(17) . . . . ?
C20 C14 C15 C17 1.9(2) . . . . ?
C13 C14 C15 C17 -176.39(16) . . . . ?
C20 C14 C15 C16 -179.93(16) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C14 C15 C17 C18 -0.3(3) . . . . ?
C16 C15 C17 C18 -178.55(18) . . . . ?
C20 N5 C18 C17 1.5(3) . . . . ?
C20 N5 C18 C19 -177.47(17) . . . . ?
C15 C17 C18 N5 -1.4(3) . . . . ?
C15 C17 C18 C19 177.49(18) . . . . ?
C18 N5 C20 N4 178.81(16) . . . . ?
C18 N5 C20 C14 0.2(2) . . . . ?
C11 N4 C20 N5 -176.82(15) . . . . ?
C11 N4 C20 C14 1.8(2) . . . . ?
C15 C14 C20 N5 -1.9(2) . . . . ?
C13 C14 C20 N5 176.49(15) . . . . ?
C15 C14 C20 N4 179.62(15) . . . . ?
C13 C14 C20 N4 -2.0(2) . . . . ?

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
N3 H3A N1 0.900(9) 2.403(11) 3.253(2) 157.5(16) 2_745

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.046

# Attachment 'B705149B_4.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 635918'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C9 H13 Cl N3 O5 Zn'

_chemical_formula_sum            'C25 H27 Cl2 N5 O4 Zn'

_chemical_formula_weight         597.79

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   12.609(3)

_cell_length_b                   15.421(3)

_cell_length_c                   14.505(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 110.09(3)

_cell_angle_gamma                90.00

_cell_volume                     2648.8(9)

_cell_formula_units_Z            4

_cell_measurement_temperature    113(2)

_cell_measurement_reflns_used    4906

_cell_measurement_theta_min      2.0

_cell_measurement_theta_max      27.9

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.08

_exptl_crystal_size_mid          0.06

_exptl_crystal_size_min          0.02

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.499

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1232

_exptl_absorpt_coefficient_mu    1.170

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.424

_exptl_absorpt_correction_T_max  0.979

_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      113(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Rigaku Saturn'

_diffrn_measurement_method       \w

_diffrn_detector_area_resol_mean 7.31

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            14790

_diffrn_reflns_av_R_equivalents  0.0445

_diffrn_reflns_av_sigmaI/netI    0.0575

_diffrn_reflns_limit_h_min       -16

_diffrn_reflns_limit_h_max       16

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       19

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         1.99

_diffrn_reflns_theta_max         27.00

_reflns_number_total             5699

_reflns_number_gt                4643

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear

_computing_cell_refinement       CrystalClear

_computing_data_reduction        CrystalStructure

_computing_structure_solution    SIR92

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    ?

_computing_publication_material  'CrystalStructure 3.7.0'

_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^)+(0.0000P)^2^+9.3407P] 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    mixed

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         5699

_refine_ls_number_parameters     343

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0814

_refine_ls_R_factor_gt           0.0627

_refine_ls_wR_factor_ref         0.1278

_refine_ls_wR_factor_gt          0.1211

_refine_ls_goodness_of_fit_ref   1.142

_refine_ls_restrained_S_all      1.142

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

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

Zn1 Zn 0.69292(4) 0.39209(3) 0.71754(3) 0.01904(12) Uani 1 1 d . . .
O1 O 0.7595(2) 0.35288(19) 0.8529(2) 0.0243(6) Uani 1 1 d . . .
N1 N 0.4426(3) 0.4709(2) 0.5818(3) 0.0230(7) Uani 1 1 d D . .
H1 H 0.3763(17) 0.488(3) 0.548(3) 0.028 Uiso 1 1 d D . .
C1 C 0.4482(3) 0.3811(3) 0.5816(3) 0.0203(8) Uani 1 1 d . . .
Cl2 Cl 1.04385(11) 0.16440(9) 0.87843(11) 0.0491(4) Uani 1 1 d . . .
O2 O 0.5852(2) 0.36590(19) 0.8563(2) 0.0286(7) Uani 1 1 d . . .
N2 N 0.5405(3) 0.3382(2) 0.6324(2) 0.0189(7) Uani 1 1 d . . .
C2 C 0.3463(3) 0.3389(3) 0.5233(3) 0.0221(8) Uani 1 1 d . . .
H2A H 0.2820 0.3719 0.4867 0.027 Uiso 1 1 calc R . .
Cl3 Cl 1.06839(11) 0.35131(9) 0.86300(10) 0.0490(3) Uani 1 1 d . . .
O3 O 0.8131(2) 0.37211(18) 0.6629(2) 0.0237(6) Uani 1 1 d . . .
N3 N 0.6327(3) 0.2106(2) 0.6909(2) 0.0215(7) Uani 1 1 d . . .
C3 C 0.3430(3) 0.2507(3) 0.5212(3) 0.0225(8) Uani 1 1 d . . .
H3A H 0.2763 0.2216 0.4821 0.027 Uiso 1 1 calc R . .
O4 O 0.7610(3) 0.4696(2) 0.5421(2) 0.0374(8) Uani 1 1 d . . .
N4 N 0.6226(3) 0.5132(2) 0.6881(2) 0.0191(7) Uani 1 1 d . . .
C4 C 0.4391(3) 0.2022(3) 0.5771(3) 0.0205(8) Uani 1 1 d . . .
N5 N 0.7993(3) 0.5521(2) 0.7880(3) 0.0241(7) Uani 1 1 d . . .
C5 C 0.5363(3) 0.2485(3) 0.6327(3) 0.0199(8) Uani 1 1 d . . .
C6 C 0.6337(4) 0.1252(3) 0.6972(3) 0.0250(9) Uani 1 1 d . . .
C7 C 0.5404(4) 0.0734(3) 0.6442(3) 0.0255(9) Uani 1 1 d . . .
H7A H 0.5454 0.0121 0.6515 0.031 Uiso 1 1 calc R . .
C8 C 0.4428(4) 0.1098(3) 0.5825(3) 0.0252(9) Uani 1 1 d . . .
C9 C 0.7404(4) 0.0837(3) 0.7643(4) 0.0352(11) Uani 1 1 d . . .
H9A H 0.7891 0.1282 0.8061 0.053 Uiso 1 1 calc R . .
H9B H 0.7801 0.0556 0.7249 0.053 Uiso 1 1 calc R . .
H9C H 0.7215 0.0402 0.8055 0.053 Uiso 1 1 calc R . .
C10 C 0.3430(4) 0.0563(3) 0.5242(3) 0.0314(10) Uani 1 1 d . . .
H10A H 0.3627 -0.0053 0.5331 0.047 Uiso 1 1 calc R . .
H10B H 0.3215 0.0713 0.4545 0.047 Uiso 1 1 calc R . .
H10C H 0.2796 0.0680 0.5468 0.047 Uiso 1 1 calc R . .
C11 C 0.5187(3) 0.5326(3) 0.6313(3) 0.0207(8) Uani 1 1 d . . .
C12 C 0.4780(4) 0.6208(3) 0.6171(3) 0.0251(9) Uani 1 1 d . . .
H12A H 0.4024 0.6327 0.5765 0.030 Uiso 1 1 calc R . .
C13 C 0.5475(4) 0.6859(3) 0.6614(3) 0.0246(9) Uani 1 1 d . . .
H13A H 0.5213 0.7441 0.6520 0.030 Uiso 1 1 calc R . .
C14 C 0.6606(3) 0.6677(3) 0.7226(3) 0.0218(8) Uani 1 1 d . . .
C15 C 0.6945(3) 0.5800(3) 0.7333(3) 0.0199(8) Uani 1 1 d . . .
C16 C 0.8733(3) 0.6127(3) 0.8351(3) 0.0271(9) Uani 1 1 d . . .
C17 C 0.8465(4) 0.7018(3) 0.8302(3) 0.0294(10) Uani 1 1 d . . .
H17A H 0.9017 0.7422 0.8671 0.035 Uiso 1 1 calc R . .
C18 C 0.7413(4) 0.7309(3) 0.7724(3) 0.0264(9) Uani 1 1 d . . .
C19 C 0.9905(4) 0.5816(3) 0.8930(4) 0.0391(12) Uani 1 1 d . . .
H19A H 0.9886 0.5191 0.9049 0.059 Uiso 1 1 calc R . .
H19B H 1.0182 0.6122 0.9560 0.059 Uiso 1 1 calc R . .
H19C H 1.0409 0.5931 0.8559 0.059 Uiso 1 1 calc R . .
C20 C 0.7128(4) 0.8257(3) 0.7616(4) 0.0319(10) Uani 1 1 d . . .
H20A H 0.7685 0.8581 0.8144 0.048 Uiso 1 1 calc R . .
H20B H 0.6374 0.8346 0.7653 0.048 Uiso 1 1 calc R . .
H20C H 0.7138 0.8462 0.6979 0.048 Uiso 1 1 calc R . .
C21 C 0.6846(4) 0.3428(2) 0.8932(3) 0.0224(8) Uani 1 1 d . . .
C22 C 0.7262(4) 0.3019(4) 0.9939(3) 0.0412(12) Uani 1 1 d . . .
H22A H 0.6636 0.2717 1.0056 0.062 Uiso 1 1 calc R . .
H22B H 0.7555 0.3471 1.0437 0.062 Uiso 1 1 calc R . .
H22C H 0.7864 0.2603 0.9978 0.062 Uiso 1 1 calc R . .
C23 C 0.8305(3) 0.4202(3) 0.5983(3) 0.0222(8) Uani 1 1 d . . .
C24 C 0.9465(4) 0.4144(3) 0.5907(4) 0.0425(13) Uani 1 1 d . . .
H24A H 0.9623 0.4676 0.5609 0.064 Uiso 1 1 calc R . .
H24B H 0.9496 0.3646 0.5498 0.064 Uiso 1 1 calc R . .
H24C H 1.0029 0.4072 0.6563 0.064 Uiso 1 1 calc R . .
C25 C 0.9760(4) 0.2622(3) 0.8277(4) 0.0403(12) Uani 1 1 d . . .
H25A H 0.9470 0.2576 0.7553 0.048 Uiso 1 1 calc R . .
H25B H 0.9107 0.2717 0.8497 0.048 Uiso 1 1 calc R . .

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

Zn1 0.0165(2) 0.0179(2) 0.0228(2) 0.00214(19) 0.00687(16) 0.0018(2)
O1 0.0205(14) 0.0290(16) 0.0248(14) 0.0023(12) 0.0097(11) -0.0005(12)
N1 0.0180(17) 0.0197(19) 0.0297(18) 0.0035(14) 0.0062(14) 0.0000(14)
C1 0.0206(19) 0.021(2) 0.0207(18) 0.0011(16) 0.0087(15) 0.0002(16)
Cl2 0.0317(6) 0.0494(8) 0.0615(8) 0.0230(7) 0.0101(6) 0.0090(6)
O2 0.0256(16) 0.0270(16) 0.0353(16) -0.0065(13) 0.0131(13) -0.0048(13)
N2 0.0158(16) 0.0185(17) 0.0218(16) 0.0000(13) 0.0056(12) -0.0001(13)
C2 0.0192(19) 0.026(2) 0.0208(19) 0.0037(16) 0.0065(15) 0.0023(17)
Cl3 0.0371(7) 0.0428(8) 0.0572(8) -0.0017(6) 0.0035(6) 0.0090(6)
O3 0.0219(14) 0.0224(15) 0.0292(15) 0.0013(12) 0.0118(12) 0.0031(12)
N3 0.0208(17) 0.0194(18) 0.0275(17) 0.0030(14) 0.0123(14) 0.0020(14)
C3 0.0197(19) 0.026(2) 0.0212(19) 0.0003(16) 0.0062(15) -0.0040(17)
O4 0.0293(17) 0.045(2) 0.0336(17) 0.0134(15) 0.0050(14) 0.0145(15)
N4 0.0196(17) 0.0186(17) 0.0211(16) -0.0003(13) 0.0095(13) -0.0015(13)
C4 0.023(2) 0.020(2) 0.0212(19) 0.0000(15) 0.0121(16) -0.0043(16)
N5 0.0219(17) 0.0230(18) 0.0278(17) -0.0005(15) 0.0092(14) -0.0001(15)
C5 0.024(2) 0.020(2) 0.0198(18) 0.0018(15) 0.0118(16) -0.0006(16)
C6 0.028(2) 0.020(2) 0.030(2) 0.0018(17) 0.0142(17) 0.0039(17)
C7 0.033(2) 0.018(2) 0.029(2) 0.0033(16) 0.0168(18) 0.0035(18)
C8 0.035(2) 0.023(2) 0.0229(19) 0.0009(17) 0.0161(17) -0.0018(19)
C9 0.031(3) 0.024(3) 0.048(3) 0.008(2) 0.011(2) 0.0048(19)
C10 0.041(3) 0.022(2) 0.031(2) -0.0039(18) 0.011(2) -0.012(2)
C11 0.022(2) 0.017(2) 0.027(2) 0.0014(16) 0.0135(16) -0.0015(16)
C12 0.025(2) 0.023(2) 0.032(2) 0.0051(17) 0.0154(17) 0.0060(18)
C13 0.032(2) 0.019(2) 0.029(2) 0.0048(17) 0.0179(18) 0.0061(17)
C14 0.027(2) 0.017(2) 0.026(2) 0.0014(16) 0.0155(17) -0.0014(17)
C15 0.0216(19) 0.022(2) 0.0211(19) 0.0014(15) 0.0135(16) -0.0011(16)
C16 0.024(2) 0.029(2) 0.030(2) -0.0031(19) 0.0113(17) -0.0036(19)
C17 0.033(2) 0.022(2) 0.038(2) -0.0056(18) 0.017(2) -0.0087(19)
C18 0.033(2) 0.021(2) 0.032(2) -0.0051(17) 0.0195(19) -0.0055(18)
C19 0.031(3) 0.036(3) 0.045(3) -0.007(2) 0.006(2) -0.003(2)
C20 0.038(3) 0.022(2) 0.041(3) -0.0045(19) 0.020(2) -0.004(2)
C21 0.031(2) 0.013(2) 0.025(2) -0.0037(15) 0.0113(17) -0.0038(17)
C22 0.046(3) 0.049(3) 0.028(2) 0.005(2) 0.012(2) -0.016(2)
C23 0.022(2) 0.024(2) 0.0213(19) 0.0002(16) 0.0083(16) 0.0023(16)
C24 0.034(3) 0.049(3) 0.055(3) 0.021(2) 0.028(2) 0.013(2)
C25 0.027(2) 0.039(3) 0.050(3) 0.008(2) 0.007(2) 0.006(2)

_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

Zn1 O1 1.947(3) . ?
Zn1 O3 1.961(3) . ?
Zn1 N4 2.048(3) . ?
Zn1 N2 2.068(3) . ?
O1 C21 1.280(5) . ?
N1 C11 1.367(5) . ?
N1 C1 1.387(5) . ?
N1 H1 0.853(10) . ?
C1 N2 1.322(5) . ?
C1 C2 1.429(5) . ?
Cl2 C25 1.765(5) . ?
O2 C21 1.235(5) . ?
N2 C5 1.384(5) . ?
C2 C3 1.360(6) . ?
C2 H2A 0.9500 . ?
Cl3 C25 1.761(5) . ?
O3 C23 1.271(5) . ?
N3 C6 1.321(5) . ?
N3 C5 1.351(5) . ?
C3 C4 1.417(6) . ?
C3 H3A 0.9500 . ?
O4 C23 1.234(5) . ?
N4 C11 1.321(5) . ?
N4 C15 1.381(5) . ?
C4 C5 1.409(6) . ?
C4 C8 1.428(6) . ?
N5 C16 1.332(5) . ?
N5 C15 1.356(5) . ?
C6 C7 1.411(6) . ?
C6 C9 1.506(6) . ?
C7 C8 1.369(6) . ?
C7 H7A 0.9500 . ?
C8 C10 1.499(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.443(6) . ?
C12 C13 1.343(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.425(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.410(6) . ?
C14 C18 1.415(6) . ?
C16 C17 1.411(6) . ?
C16 C19 1.505(6) . ?
C17 C18 1.379(6) . ?
C17 H17A 0.9500 . ?
C18 C20 1.500(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.510(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.507(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

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

O1 Zn1 O3 103.50(12) . . ?
O1 Zn1 N4 119.93(12) . . ?
O3 Zn1 N4 113.46(12) . . ?
O1 Zn1 N2 117.87(13) . . ?
O3 Zn1 N2 112.59(12) . . ?
N4 Zn1 N2 89.71(13) . . ?
C21 O1 Zn1 111.6(3) . . ?
C11 N1 C1 132.1(3) . . ?
C11 N1 H1 117(3) . . ?
C1 N1 H1 110(3) . . ?
N2 C1 N1 122.3(4) . . ?
N2 C1 C2 122.8(4) . . ?
N1 C1 C2 114.9(3) . . ?
C1 N2 C5 118.4(3) . . ?
C1 N2 Zn1 126.3(3) . . ?
C5 N2 Zn1 115.3(3) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C23 O3 Zn1 124.0(3) . . ?
C6 N3 C5 117.4(4) . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C11 N4 C15 118.4(3) . . ?
C11 N4 Zn1 127.0(3) . . ?
C15 N4 Zn1 114.5(3) . . ?
C5 C4 C3 117.7(4) . . ?
C5 C4 C8 117.9(4) . . ?
C3 C4 C8 124.3(4) . . ?
C16 N5 C15 116.6(4) . . ?
N3 C5 N2 114.0(3) . . ?
N3 C5 C4 123.9(4) . . ?
N2 C5 C4 122.1(4) . . ?
N3 C6 C7 122.7(4) . . ?
N3 C6 C9 117.0(4) . . ?
C7 C6 C9 120.3(4) . . ?
C8 C7 C6 121.2(4) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C7 C8 C4 116.8(4) . . ?
C7 C8 C10 122.3(4) . . ?
C4 C8 C10 120.8(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 N1 122.4(4) . . ?
N4 C11 C12 122.1(4) . . ?
N1 C11 C12 115.5(4) . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C15 C14 C18 117.8(4) . . ?
C15 C14 C13 117.3(4) . . ?
C18 C14 C13 124.9(4) . . ?
N5 C15 N4 112.9(3) . . ?
N5 C15 C14 124.5(4) . . ?
N4 C15 C14 122.6(4) . . ?
N5 C16 C17 122.9(4) . . ?
N5 C16 C19 116.3(4) . . ?
C17 C16 C19 120.7(4) . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C14 117.3(4) . . ?
C17 C18 C20 121.8(4) . . ?
C14 C18 C20 120.9(4) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O1 124.4(4) . . ?
O2 C21 C22 120.3(4) . . ?
O1 C21 C22 115.3(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 O3 125.8(4) . . ?
O4 C23 C24 118.3(4) . . ?
O3 C23 C24 115.9(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl3 C25 Cl2 111.6(3) . . ?
Cl3 C25 H25A 109.3 . . ?
Cl2 C25 H25A 109.3 . . ?
Cl3 C25 H25B 109.3 . . ?
Cl2 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?

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

O3 Zn1 O1 C21 -165.1(3) . . . . ?
N4 Zn1 O1 C21 67.2(3) . . . . ?
N2 Zn1 O1 C21 -40.1(3) . . . . ?
C11 N1 C1 N2 -3.1(7) . . . . ?
C11 N1 C1 C2 176.2(4) . . . . ?
N1 C1 N2 C5 176.1(3) . . . . ?
C2 C1 N2 C5 -3.2(5) . . . . ?
N1 C1 N2 Zn1 -1.6(5) . . . . ?
C2 C1 N2 Zn1 179.1(3) . . . . ?
O1 Zn1 N2 C1 127.4(3) . . . . ?
O3 Zn1 N2 C1 -112.2(3) . . . . ?
N4 Zn1 N2 C1 3.2(3) . . . . ?
O1 Zn1 N2 C5 -50.4(3) . . . . ?
O3 Zn1 N2 C5 70.0(3) . . . . ?
N4 Zn1 N2 C5 -174.5(3) . . . . ?
N2 C1 C2 C3 1.3(6) . . . . ?
N1 C1 C2 C3 -178.0(3) . . . . ?
O1 Zn1 O3 C23 -146.1(3) . . . . ?
N4 Zn1 O3 C23 -14.6(3) . . . . ?
N2 Zn1 O3 C23 85.5(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
O1 Zn1 N4 C11 -124.3(3) . . . . ?
O3 Zn1 N4 C11 112.7(3) . . . . ?
N2 Zn1 N4 C11 -1.9(3) . . . . ?
O1 Zn1 N4 C15 56.1(3) . . . . ?
O3 Zn1 N4 C15 -66.8(3) . . . . ?
N2 Zn1 N4 C15 178.5(3) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C2 C3 C4 C8 177.7(4) . . . . ?
C6 N3 C5 N2 177.9(3) . . . . ?
C6 N3 C5 C4 -1.8(6) . . . . ?
C1 N2 C5 N3 -176.6(3) . . . . ?
Zn1 N2 C5 N3 1.4(4) . . . . ?
C1 N2 C5 C4 3.1(5) . . . . ?
Zn1 N2 C5 C4 -178.9(3) . . . . ?
C3 C4 C5 N3 178.5(3) . . . . ?
C8 C4 C5 N3 -0.1(6) . . . . ?
C3 C4 C5 N2 -1.2(5) . . . . ?
C8 C4 C5 N2 -179.7(3) . . . . ?
C5 N3 C6 C7 1.8(6) . . . . ?
C5 N3 C6 C9 -178.4(4) . . . . ?
N3 C6 C7 C8 0.1(6) . . . . ?
C9 C6 C7 C8 -179.7(4) . . . . ?
C6 C7 C8 C4 -1.9(6) . . . . ?
C6 C7 C8 C10 179.1(4) . . . . ?
C5 C4 C8 C7 1.9(5) . . . . ?
C3 C4 C8 C7 -176.5(4) . . . . ?
C5 C4 C8 C10 -179.1(3) . . . . ?
C3 C4 C8 C10 2.4(6) . . . . ?
C15 N4 C11 N1 178.4(3) . . . . ?
Zn1 N4 C11 N1 -1.1(5) . . . . ?
C15 N4 C11 C12 -1.2(5) . . . . ?
Zn1 N4 C11 C12 179.2(3) . . . . ?
C1 N1 C11 N4 4.6(7) . . . . ?
C1 N1 C11 C12 -175.7(4) . . . . ?
N4 C11 C12 C13 0.9(6) . . . . ?
N1 C11 C12 C13 -178.8(4) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C12 C13 C14 C18 179.6(4) . . . . ?
C16 N5 C15 N4 -179.1(3) . . . . ?
C16 N5 C15 C14 0.9(6) . . . . ?
C11 N4 C15 N5 -178.8(3) . . . . ?
Zn1 N4 C15 N5 0.8(4) . . . . ?
C11 N4 C15 C14 1.2(5) . . . . ?
Zn1 N4 C15 C14 -179.2(3) . . . . ?
C18 C14 C15 N5 -0.1(6) . . . . ?
C13 C14 C15 N5 179.3(3) . . . . ?
C18 C14 C15 N4 179.9(3) . . . . ?
C13 C14 C15 N4 -0.6(5) . . . . ?
C15 N5 C16 C17 0.2(6) . . . . ?
C15 N5 C16 C19 -178.1(4) . . . . ?
N5 C16 C17 C18 -2.2(7) . . . . ?
C19 C16 C17 C18 176.0(4) . . . . ?
C16 C17 C18 C14 2.9(6) . . . . ?
C16 C17 C18 C20 -176.6(4) . . . . ?
C15 C14 C18 C17 -1.8(6) . . . . ?
C13 C14 C18 C17 178.9(4) . . . . ?
C15 C14 C18 C20 177.7(4) . . . . ?
C13 C14 C18 C20 -1.7(6) . . . . ?
Zn1 O1 C21 O2 -9.2(5) . . . . ?
Zn1 O1 C21 C22 172.7(3) . . . . ?
Zn1 O3 C23 O4 -21.1(6) . . . . ?
Zn1 O3 C23 C24 159.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        27.00

_diffrn_measured_fraction_theta_full 0.986

_refine_diff_density_max         0.511

_refine_diff_density_min         -0.669

_refine_diff_density_rms         0.091