Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Ezequiel M. Vazquez-Lopez'
_publ_contact_author_address     
;
Departamento de Quimica Inorgancia
Universidade de Vigo
Facultade de Quimica
Edificio de Ciencias Experimentais
Vigo
Galicia
E-36310
SPAIN
;

_publ_contact_author_email       EZEQUIEL@UVIGO.ES

_publ_section_title              
;
Synthesis and Structure of
2-acetylpyridine-salicyloylhydrazone and its
Copper(II) and Zinc(II) Complexes. The effect of
the metal coordination on the weak intermolecular
interactions
;
loop_
_publ_author_name
'Ezequiel M. Vazquez-Lopez'
'Paula Barbazan'
'Rosa Carballo'
#===============================================================================
###############
# CCDC 639030 #
###############

data_H2L
_database_code_depnum_ccdc_archive 'CCDC 639030'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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'
'-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                   12.8373(14)
_cell_length_b                   11.8355(13)
_cell_length_c                   16.975(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2579.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.498659
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            12238
_diffrn_reflns_av_R_equivalents  0.1297
_diffrn_reflns_av_sigmaI/netI    0.2318
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         28.06
_reflns_number_total             3032
_reflns_number_gt                841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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^)+(0.0449P)^2^+0.0000P] 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_number_reflns         3032
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2955
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   0.799
_refine_ls_restrained_S_all      0.799
_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
O1 O 0.0195(2) 0.3149(2) 0.48689(16) 0.0976(10) Uani 1 1 d . . .
O2 O 0.33137(16) 0.23553(19) 0.47681(12) 0.0605(7) Uani 1 1 d . . .
H2 H 0.3912 0.2118 0.4804 0.073 Uiso 1 1 calc R . .
N1 N 0.17036(19) 0.3504(2) 0.42795(16) 0.0508(8) Uani 1 1 d . . .
H1 H 0.2353 0.3345 0.4226 0.061 Uiso 1 1 calc R . .
N2 N 0.1274(2) 0.4392(2) 0.38604(16) 0.0493(8) Uani 1 1 d . . .
N3 N 0.2082(2) 0.6628(3) 0.26408(17) 0.0564(8) Uani 1 1 d . . .
C1 C 0.1109(3) 0.2892(3) 0.4768(2) 0.0546(10) Uani 1 1 d . . .
C2 C 0.1596(3) 0.1915(3) 0.51762(19) 0.0467(9) Uani 1 1 d . . .
C3 C 0.2657(3) 0.1651(3) 0.51658(19) 0.0440(9) Uani 1 1 d . . .
C4 C 0.3027(3) 0.0707(3) 0.55475(19) 0.0508(10) Uani 1 1 d . . .
H4 H 0.3735 0.0542 0.5538 0.061 Uiso 1 1 calc R . .
C5 C 0.2353(3) 0.0010(3) 0.5942(2) 0.0671(11) Uani 1 1 d . . .
H5 H 0.2606 -0.0633 0.6193 0.081 Uiso 1 1 calc R . .
C6 C 0.1310(3) 0.0251(3) 0.5971(2) 0.0774(13) Uani 1 1 d . . .
H6 H 0.0856 -0.0218 0.6244 0.093 Uiso 1 1 calc R . .
C7 C 0.0945(3) 0.1194(3) 0.5591(2) 0.0704(12) Uani 1 1 d . . .
H7 H 0.0237 0.1354 0.5612 0.084 Uiso 1 1 calc R . .
C8 C 0.1924(3) 0.5040(3) 0.34980(19) 0.0430(9) Uani 1 1 d . . .
C9 C 0.1439(3) 0.5971(3) 0.30481(19) 0.0442(9) Uani 1 1 d . . .
C13 C 0.1666(4) 0.7462(3) 0.2214(2) 0.0704(12) Uani 1 1 d . . .
H13 H 0.2113 0.7924 0.1928 0.084 Uiso 1 1 calc R . .
C10 C 0.0371(3) 0.6150(3) 0.3048(2) 0.0627(11) Uani 1 1 d . . .
H10 H -0.0062 0.5691 0.3349 0.075 Uiso 1 1 calc R . .
C11 C -0.0049(3) 0.7014(4) 0.2601(2) 0.0729(12) Uani 1 1 d . . .
H11 H -0.0763 0.7144 0.2590 0.087 Uiso 1 1 calc R . .
C12 C 0.0624(4) 0.7674(3) 0.2172(2) 0.0741(13) Uani 1 1 d . . .
H12 H 0.0373 0.8257 0.1858 0.089 Uiso 1 1 calc R . .
C14 C 0.3086(3) 0.4934(3) 0.3520(2) 0.0654(11) Uani 1 1 d . . .
H14A H 0.3296 0.4622 0.4017 0.098 Uiso 1 1 calc R . .
H14B H 0.3396 0.5666 0.3453 0.098 Uiso 1 1 calc R . .
H14C H 0.3312 0.4444 0.3102 0.098 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
O1 0.0400(16) 0.109(2) 0.144(3) 0.0630(19) 0.0274(17) 0.0124(14)
O2 0.0356(13) 0.0666(18) 0.0795(17) 0.0241(15) 0.0008(12) 0.0003(13)
N1 0.0319(16) 0.0543(19) 0.066(2) 0.0094(17) 0.0057(16) -0.0002(16)
N2 0.0461(19) 0.0489(19) 0.0528(19) 0.0063(16) -0.0051(16) 0.0040(16)
N3 0.063(2) 0.051(2) 0.055(2) 0.0084(18) 0.0035(17) -0.0014(18)
C1 0.036(2) 0.062(3) 0.067(3) 0.006(2) 0.007(2) -0.009(2)
C2 0.042(2) 0.044(2) 0.054(2) 0.0097(19) 0.0018(19) -0.0007(19)
C3 0.046(2) 0.043(2) 0.043(2) 0.004(2) -0.0001(19) -0.0022(19)
C4 0.050(2) 0.048(2) 0.054(2) 0.003(2) -0.006(2) 0.003(2)
C5 0.075(3) 0.053(3) 0.074(3) 0.013(2) 0.004(3) 0.001(2)
C6 0.068(3) 0.074(3) 0.091(3) 0.035(3) 0.022(3) -0.006(2)
C7 0.052(3) 0.071(3) 0.088(3) 0.024(3) 0.018(2) -0.004(2)
C8 0.040(2) 0.047(2) 0.042(2) -0.0028(19) 0.0014(18) -0.003(2)
C9 0.050(2) 0.046(2) 0.036(2) -0.0028(19) -0.0030(18) 0.004(2)
C13 0.087(3) 0.058(3) 0.066(3) 0.014(2) 0.001(2) 0.002(3)
C10 0.054(3) 0.063(3) 0.071(3) 0.004(2) -0.002(2) 0.006(2)
C11 0.060(3) 0.077(3) 0.081(3) 0.004(3) -0.018(2) 0.014(3)
C12 0.088(3) 0.061(3) 0.074(3) 0.007(2) -0.021(3) 0.010(3)
C14 0.051(3) 0.070(3) 0.075(3) 0.011(2) 0.006(2) 0.001(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
O1 C1 1.225(3) . ?
O2 C3 1.364(3) . ?
N1 C1 1.339(4) . ?
N1 N2 1.384(3) . ?
N2 C8 1.290(4) . ?
N3 C9 1.329(4) . ?
N3 C13 1.336(4) . ?
C1 C2 1.485(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.370(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.371(4) . ?
C8 C9 1.478(4) . ?
C8 C14 1.497(4) . ?
C9 C10 1.388(4) . ?
C13 C12 1.362(5) . ?
C10 C11 1.382(4) . ?
C11 C12 1.373(5) . ?

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
C1 N1 N2 120.1(3) . . ?
C8 N2 N1 116.0(3) . . ?
C9 N3 C13 117.8(3) . . ?
O1 C1 N1 119.9(3) . . ?
O1 C1 C2 122.1(3) . . ?
N1 C1 C2 118.0(3) . . ?
C7 C2 C3 117.1(3) . . ?
C7 C2 C1 117.6(3) . . ?
C3 C2 C1 125.3(3) . . ?
O2 C3 C4 121.0(3) . . ?
O2 C3 C2 118.1(3) . . ?
C4 C3 C2 120.8(3) . . ?
C5 C4 C3 120.1(3) . . ?
C4 C5 C6 120.6(4) . . ?
C7 C6 C5 119.2(4) . . ?
C6 C7 C2 122.3(4) . . ?
N2 C8 C9 114.6(3) . . ?
N2 C8 C14 125.6(3) . . ?
C9 C8 C14 119.7(3) . . ?
N3 C9 C10 121.6(3) . . ?
N3 C9 C8 116.3(3) . . ?
C10 C9 C8 122.1(4) . . ?
N3 C13 C12 123.9(4) . . ?
C11 C10 C9 119.8(4) . . ?
C12 C11 C10 117.8(4) . . ?
C13 C12 C11 119.0(4) . . ?

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 H1 O2 0.86 1.93 2.609(3) 134.5 .
O2 H2 O1 0.82 1.77 2.563(3) 163.2 3_556

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        28.06
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.041

###############
# CCDC 639031 #
###############

data_[CuBr(HL)]
_database_code_depnum_ccdc_archive 'CCDC 639031'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Br Cu N3 O2'
_chemical_formula_weight         397.72

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7539(9)
_cell_length_b                   9.3441(12)
_cell_length_c                   11.4902(15)
_cell_angle_alpha                89.773(3)
_cell_angle_beta                 81.497(3)
_cell_angle_gamma                88.363(3)
_cell_volume                     716.87(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             394
_exptl_absorpt_coefficient_mu    4.317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.627515
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            4816
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.1634
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         28.07
_reflns_number_total             3320
_reflns_number_gt                1441
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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^)+(0.0338P)^2^+0.0000P] 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_number_reflns         3320
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   0.752
_refine_ls_restrained_S_all      0.752
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

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
Cu Cu 0.20682(11) 0.09714(6) 0.12189(6) 0.0420(2) Uani 1 1 d . . .
Br Br 0.15097(12) 0.28208(6) 0.25726(6) 0.0717(3) Uani 1 1 d . . .
O1 O 0.2373(6) 0.2115(3) -0.0212(3) 0.0481(10) Uani 1 1 d . . .
C2 C 0.2949(8) 0.2048(6) -0.2296(5) 0.0398(14) Uani 1 1 d . . .
N3 N 0.1948(6) -0.0723(4) 0.2267(4) 0.0368(11) Uani 1 1 d . . .
N1 N 0.2785(6) -0.0093(4) -0.1110(4) 0.0444(12) Uani 1 1 d . . .
C8 C 0.2525(8) -0.1827(5) 0.0381(5) 0.0427(14) Uani 1 1 d . . .
N2 N 0.2512(6) -0.0513(4) 0.0041(4) 0.0389(11) Uani 1 1 d . . .
C9 C 0.2193(7) -0.1991(5) 0.1663(5) 0.0378(13) Uani 1 1 d . . .
C1 C 0.2670(8) 0.1350(6) -0.1138(5) 0.0414(14) Uani 1 1 d . . .
O2 O 0.3390(6) -0.0151(4) -0.3409(3) 0.0607(12) Uani 1 1 d . . .
H2 H 0.3198 -0.0472 -0.2738 0.073 Uiso 1 1 calc R . .
C3 C 0.3323(8) 0.1273(6) -0.3369(5) 0.0424(14) Uani 1 1 d . . .
C4 C 0.3593(8) 0.2013(7) -0.4422(5) 0.0489(15) Uani 1 1 d . . .
H4 H 0.3872 0.1511 -0.5127 0.059 Uiso 1 1 calc R . .
C6 C 0.3078(9) 0.4245(6) -0.3396(6) 0.0551(17) Uani 1 1 d . . .
H6 H 0.2990 0.5240 -0.3412 0.066 Uiso 1 1 calc R . .
C13 C 0.1634(8) -0.0768(6) 0.3426(5) 0.0445(14) Uani 1 1 d . . .
H13 H 0.1469 0.0093 0.3836 0.053 Uiso 1 1 calc R . .
C12 C 0.1540(9) -0.2025(7) 0.4063(6) 0.0567(17) Uani 1 1 d . . .
H12 H 0.1328 -0.2013 0.4881 0.068 Uiso 1 1 calc R . .
C7 C 0.2842(8) 0.3530(6) -0.2358(5) 0.0460(15) Uani 1 1 d . . .
H7 H 0.2600 0.4053 -0.1662 0.055 Uiso 1 1 calc R . .
C10 C 0.2123(8) -0.3269(6) 0.2261(6) 0.0517(16) Uani 1 1 d . . .
H10 H 0.2319 -0.4127 0.1846 0.062 Uiso 1 1 calc R . .
C5 C 0.3456(9) 0.3460(7) -0.4436(5) 0.0554(16) Uani 1 1 d . . .
H5 H 0.3617 0.3939 -0.5153 0.066 Uiso 1 1 calc R . .
C11 C 0.1765(9) -0.3285(6) 0.3461(6) 0.0531(17) Uani 1 1 d . . .
H11 H 0.1676 -0.4150 0.3865 0.064 Uiso 1 1 calc R . .
C14 C 0.2862(9) -0.3068(5) -0.0451(5) 0.0611(18) Uani 1 1 d . . .
H14A H 0.1594 -0.3438 -0.0568 0.092 Uiso 1 1 calc R . .
H14B H 0.3639 -0.3804 -0.0128 0.092 Uiso 1 1 calc R . .
H14C H 0.3568 -0.2758 -0.1192 0.092 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
Cu 0.0548(5) 0.0327(4) 0.0382(5) 0.0008(3) -0.0056(4) -0.0028(3)
Br 0.1304(8) 0.0388(4) 0.0446(4) -0.0049(3) -0.0086(4) -0.0009(4)
O1 0.071(3) 0.034(2) 0.039(2) -0.0004(17) -0.004(2) -0.001(2)
C2 0.029(3) 0.049(3) 0.041(4) 0.005(3) -0.003(3) -0.003(3)
N3 0.034(3) 0.038(2) 0.039(3) 0.009(2) -0.005(2) -0.007(2)
N1 0.046(3) 0.042(3) 0.046(3) -0.001(2) -0.009(2) -0.001(2)
C8 0.034(4) 0.037(3) 0.057(4) 0.002(3) -0.006(3) 0.000(3)
N2 0.047(3) 0.033(2) 0.038(3) 0.002(2) -0.009(2) -0.009(2)
C9 0.029(3) 0.033(3) 0.052(4) 0.008(3) -0.008(3) 0.001(3)
C1 0.038(4) 0.044(3) 0.042(4) 0.004(3) -0.006(3) 0.003(3)
O2 0.079(3) 0.054(3) 0.046(3) -0.003(2) 0.002(2) -0.005(2)
C3 0.030(3) 0.050(4) 0.046(4) 0.000(3) -0.004(3) -0.003(3)
C4 0.032(4) 0.078(4) 0.035(4) 0.000(3) 0.002(3) -0.003(3)
C6 0.050(4) 0.052(4) 0.064(5) 0.018(3) -0.009(4) -0.005(3)
C13 0.040(4) 0.052(4) 0.042(4) 0.003(3) -0.006(3) -0.004(3)
C12 0.051(4) 0.068(4) 0.051(4) 0.024(3) -0.008(3) -0.002(4)
C7 0.044(4) 0.047(3) 0.045(4) 0.005(3) -0.002(3) -0.004(3)
C10 0.046(4) 0.037(3) 0.073(5) 0.007(3) -0.012(4) 0.000(3)
C5 0.041(4) 0.081(5) 0.043(4) 0.022(3) -0.002(3) -0.004(4)
C11 0.043(4) 0.044(4) 0.072(5) 0.025(3) -0.009(3) -0.006(3)
C14 0.075(5) 0.040(3) 0.067(5) -0.009(3) -0.010(4) 0.005(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
Cu N2 1.928(4) . ?
Cu O1 1.946(3) . ?
Cu N3 1.982(4) . ?
Cu Br 2.3149(9) . ?
O1 C1 1.271(6) . ?
C2 C7 1.387(7) . ?
C2 C3 1.419(7) . ?
C2 C1 1.468(7) . ?
N3 C13 1.318(6) . ?
N3 C9 1.369(6) . ?
N1 C1 1.349(6) . ?
N1 N2 1.366(6) . ?
C8 N2 1.287(6) . ?
C8 C9 1.465(7) . ?
C8 C14 1.497(7) . ?
C9 C10 1.374(7) . ?
O2 C3 1.331(6) . ?
C3 C4 1.382(7) . ?
C4 C5 1.353(7) . ?
C6 C7 1.356(7) . ?
C6 C5 1.392(8) . ?
C13 C12 1.379(7) . ?
C12 C11 1.361(8) . ?
C10 C11 1.364(8) . ?

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 Cu O1 79.32(16) . . ?
N2 Cu N3 80.92(18) . . ?
O1 Cu N3 160.23(17) . . ?
N2 Cu Br 177.61(13) . . ?
O1 Cu Br 98.36(10) . . ?
N3 Cu Br 101.40(13) . . ?
C1 O1 Cu 112.5(3) . . ?
C7 C2 C3 117.8(5) . . ?
C7 C2 C1 119.3(5) . . ?
C3 C2 C1 122.9(5) . . ?
C13 N3 C9 118.3(5) . . ?
C13 N3 Cu 128.8(4) . . ?
C9 N3 Cu 113.0(4) . . ?
C1 N1 N2 108.0(4) . . ?
N2 C8 C9 113.5(5) . . ?
N2 C8 C14 123.4(5) . . ?
C9 C8 C14 123.2(5) . . ?
C8 N2 N1 124.2(4) . . ?
C8 N2 Cu 118.6(4) . . ?
N1 N2 Cu 117.3(3) . . ?
N3 C9 C10 120.3(5) . . ?
N3 C9 C8 114.1(4) . . ?
C10 C9 C8 125.6(5) . . ?
O1 C1 N1 122.9(5) . . ?
O1 C1 C2 119.5(5) . . ?
N1 C1 C2 117.7(5) . . ?
O2 C3 C4 118.0(5) . . ?
O2 C3 C2 122.7(5) . . ?
C4 C3 C2 119.3(5) . . ?
C5 C4 C3 120.6(6) . . ?
C7 C6 C5 118.6(6) . . ?
N3 C13 C12 123.5(5) . . ?
C11 C12 C13 118.2(6) . . ?
C6 C7 C2 122.4(6) . . ?
C11 C10 C9 120.2(5) . . ?
C4 C5 C6 121.2(6) . . ?
C10 C11 C12 119.6(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
O2 H2 N1 0.82 1.88 2.613(6) 147.6 .
C4 H4 O2 0.93 2.61 3.423(7) 146.0 2_654
C10 H10 Br 0.93 3.01 3.698(5) 132.0 1_545

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        28.07
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.102

###############
# CCDC 639032 #
###############

data_[Zn(HL)2]
_database_code_depnum_ccdc_archive 'CCDC 639032'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N6 O4 Zn'
_chemical_formula_weight         573.90

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Aba2

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

_cell_length_a                   12.598(4)
_cell_length_b                   18.483(6)
_cell_length_c                   10.818(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2518.9(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.780641
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            8039
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.1056
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.01
_reflns_number_total             2948
_reflns_number_gt                1533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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^)+(0.0187P)^2^+0.0000P] 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   0.068(18)
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.888
_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
Zn Zn 0.0000 0.0000 0.27776(8) 0.05165(19) Uani 1 2 d S . .
O1 O -0.0093(2) 0.08675(16) 0.4089(3) 0.0610(8) Uani 1 1 d . . .
O2 O 0.2863(3) 0.1637(2) 0.5313(4) 0.0944(13) Uani 1 1 d . . .
H2 H 0.2732 0.1374 0.4723 0.113 Uiso 1 1 calc R . .
N1 N 0.1731(3) 0.08986(18) 0.3845(3) 0.0511(10) Uani 1 1 d . . .
N2 N 0.1540(2) 0.03989(19) 0.2936(5) 0.0522(10) Uani 1 1 d . . .
N3 N 0.0883(3) -0.0571(2) 0.1364(3) 0.0510(10) Uani 1 1 d . . .
C1 C 0.0818(3) 0.1108(2) 0.4372(4) 0.0467(11) Uani 1 1 d . . .
C2 C 0.0941(3) 0.1659(2) 0.5371(4) 0.0499(12) Uani 1 1 d . . .
C3 C 0.1943(4) 0.1869(3) 0.5823(5) 0.0670(15) Uani 1 1 d . . .
C4 C 0.1991(4) 0.2334(3) 0.6842(5) 0.0858(18) Uani 1 1 d . . .
H4 H 0.2648 0.2473 0.7155 0.103 Uiso 1 1 calc R . .
C5 C 0.1098(4) 0.2583(3) 0.7373(5) 0.0835(19) Uani 1 1 d . . .
H5 H 0.1147 0.2886 0.8057 0.100 Uiso 1 1 calc R . .
C6 C 0.0112(5) 0.2399(3) 0.6926(5) 0.0782(15) Uani 1 1 d . . .
H6 H -0.0498 0.2588 0.7288 0.094 Uiso 1 1 calc R . .
C7 C 0.0038(4) 0.1935(2) 0.5944(4) 0.0652(12) Uani 1 1 d . . .
H7 H -0.0629 0.1802 0.5654 0.078 Uiso 1 1 calc R . .
C8 C 0.2289(3) 0.0109(2) 0.2300(4) 0.0562(13) Uani 1 1 d . . .
C9 C 0.1934(4) -0.0402(3) 0.1348(4) 0.0542(12) Uani 1 1 d . . .
C10 C 0.2618(5) -0.0698(2) 0.0480(6) 0.0728(17) Uani 1 1 d . . .
H10 H 0.3341 -0.0596 0.0493 0.087 Uiso 1 1 calc R . .
C11 C 0.2188(4) -0.1146(3) -0.0400(5) 0.0760(16) Uani 1 1 d . . .
H11 H 0.2627 -0.1334 -0.1013 0.091 Uiso 1 1 calc R . .
C12 C 0.1122(5) -0.1326(3) -0.0404(5) 0.0809(17) Uani 1 1 d . . .
H12 H 0.0833 -0.1638 -0.0988 0.097 Uiso 1 1 calc R . .
C13 C 0.0507(4) -0.1009(3) 0.0525(5) 0.0749(16) Uani 1 1 d . . .
H13 H -0.0214 -0.1117 0.0547 0.090 Uiso 1 1 d R . .
C14 C 0.3455(3) 0.0285(2) 0.2504(6) 0.0768(19) Uani 1 1 d . . .
H14A H 0.3735 -0.0019 0.3146 0.115 Uiso 1 1 d R . .
H14B H 0.3842 0.0202 0.1752 0.115 Uiso 1 1 d R . .
H14C H 0.3526 0.0783 0.2742 0.115 Uiso 1 1 d 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
Zn 0.0302(3) 0.0744(4) 0.0504(3) 0.000 0.000 -0.0019(4)
O1 0.0317(17) 0.087(2) 0.065(2) -0.0112(17) 0.0001(18) -0.0146(16)
O2 0.047(3) 0.108(3) 0.128(3) -0.028(3) -0.014(3) -0.006(2)
N1 0.047(2) 0.047(2) 0.059(3) -0.004(2) -0.0004(19) -0.0022(18)
N2 0.0348(19) 0.064(2) 0.058(3) 0.016(3) 0.002(2) 0.0033(16)
N3 0.046(3) 0.053(2) 0.054(3) 0.009(2) 0.008(2) 0.006(2)
C1 0.044(3) 0.050(3) 0.047(3) 0.009(2) -0.003(2) -0.005(2)
C2 0.040(3) 0.058(3) 0.053(3) 0.005(3) -0.007(2) -0.012(2)
C3 0.051(3) 0.069(4) 0.082(4) -0.005(3) -0.011(3) 0.000(3)
C4 0.055(4) 0.106(5) 0.096(5) -0.023(4) -0.024(3) -0.013(3)
C5 0.089(4) 0.075(4) 0.087(5) -0.021(3) -0.010(3) -0.020(3)
C6 0.057(3) 0.096(4) 0.082(3) -0.022(3) -0.001(3) -0.016(3)
C7 0.045(3) 0.079(3) 0.072(3) -0.011(3) -0.003(3) -0.016(3)
C8 0.036(2) 0.062(3) 0.070(4) 0.012(3) 0.008(2) -0.002(2)
C9 0.048(3) 0.053(3) 0.061(3) 0.013(3) 0.008(3) 0.010(2)
C10 0.071(4) 0.064(3) 0.084(5) 0.014(4) 0.021(4) 0.028(3)
C11 0.086(4) 0.066(4) 0.075(4) 0.010(3) 0.028(4) 0.029(3)
C12 0.099(5) 0.073(4) 0.070(4) -0.014(3) 0.007(4) 0.024(4)
C13 0.068(4) 0.085(4) 0.071(4) 0.006(4) -0.005(3) 0.005(3)
C14 0.031(2) 0.081(3) 0.119(6) 0.018(3) 0.003(3) 0.0021(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
Zn N2 2.082(3) . ?
Zn N2 2.082(3) 2 ?
Zn O1 2.144(3) . ?
Zn O1 2.144(3) 2 ?
Zn N3 2.166(4) . ?
Zn N3 2.166(4) 2 ?
O1 C1 1.268(4) . ?
O2 C3 1.353(5) . ?
N1 C1 1.341(5) . ?
N1 N2 1.371(5) . ?
N2 C8 1.286(5) . ?
N3 C13 1.306(6) . ?
N3 C9 1.360(5) . ?
C1 C2 1.493(6) . ?
C2 C7 1.393(6) . ?
C2 C3 1.408(6) . ?
C3 C4 1.400(7) . ?
C4 C5 1.345(6) . ?
C5 C6 1.375(7) . ?
C6 C7 1.368(6) . ?
C8 C9 1.467(6) . ?
C8 C14 1.521(5) . ?
C9 C10 1.387(6) . ?
C10 C11 1.373(7) . ?
C11 C12 1.384(7) . ?
C12 C13 1.397(7) . ?

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 Zn N2 170.6(3) . 2 ?
N2 Zn O1 74.44(15) . . ?
N2 Zn O1 99.18(14) 2 . ?
N2 Zn O1 99.17(14) . 2 ?
N2 Zn O1 74.44(15) 2 2 ?
O1 Zn O1 97.15(16) . 2 ?
N2 Zn N3 75.64(18) . . ?
N2 Zn N3 111.36(16) 2 . ?
O1 Zn N3 149.28(12) . . ?
O1 Zn N3 94.29(12) 2 . ?
N2 Zn N3 111.36(16) . 2 ?
N2 Zn N3 75.64(18) 2 2 ?
O1 Zn N3 94.29(12) . 2 ?
O1 Zn N3 149.28(12) 2 2 ?
N3 Zn N3 90.2(2) . 2 ?
C1 O1 Zn 111.8(3) . . ?
C1 N1 N2 110.4(4) . . ?
C8 N2 N1 122.4(4) . . ?
C8 N2 Zn 119.5(3) . . ?
N1 N2 Zn 117.5(3) . . ?
C13 N3 C9 119.1(4) . . ?
C13 N3 Zn 127.4(4) . . ?
C9 N3 Zn 113.4(3) . . ?
O1 C1 N1 124.9(4) . . ?
O1 C1 C2 120.5(4) . . ?
N1 C1 C2 114.6(4) . . ?
C7 C2 C3 118.5(5) . . ?
C7 C2 C1 119.2(4) . . ?
C3 C2 C1 122.2(4) . . ?
O2 C3 C4 118.5(5) . . ?
O2 C3 C2 122.6(5) . . ?
C4 C3 C2 118.8(5) . . ?
C5 C4 C3 120.6(5) . . ?
C4 C5 C6 121.5(6) . . ?
C7 C6 C5 119.3(6) . . ?
C6 C7 C2 121.3(5) . . ?
N2 C8 C9 114.9(4) . . ?
N2 C8 C14 122.9(4) . . ?
C9 C8 C14 122.3(4) . . ?
N3 C9 C10 121.5(5) . . ?
N3 C9 C8 115.8(4) . . ?
C10 C9 C8 122.7(5) . . ?
C11 C10 C9 117.5(6) . . ?
C10 C11 C12 122.0(5) . . ?
C11 C12 C13 115.8(5) . . ?
N3 C13 C12 124.0(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
O2 H2 N1 0.82 1.81 2.533(5) 147.0 .
C10 H10 O1 0.93 2.54 3.267(7) 135.4 4_554

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.046


