#=======================================================================

data_global
_audit_creation_method           'SHELXL-97 and manual editing' 

#=======================================================================
# 1. SUBMISSION DETAILS

_publ_contact_author_name          'Dr Ivo Vencato' 
_publ_contact_author_address  
;
    Instituto de Física - UFG 
    74001-970 Goiânia, GO 
    Brazil
;
_publ_contact_author_email         vencato@fis.ufg.br
_publ_contact_author_fax           '55(2162)5211014'    
_publ_contact_author_phone         '55(2162)5211014'  
_publ_contact_letter

; 
    This is a paper being submittet for publication in
    Acta Crystallographica C
    
    Date of checkcif:    August 22th, 2002.
    Date of submission:  
    Date of new checkcif:   
;
_publ_requested_coeditor_name            ?
_publ_requested_journal        'Acta Crystallographica Section C'
_publ_requested_category                'FO'

#=======================================================================

# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic            ?
_journal_date_to_coeditor                ?
_journal_date_from_coeditor              ?
_journal_date_accepted                   ?
_journal_date_printers_first             ?
_journal_date_printers_final             ?
_journal_date_proofs_out                 ?
_journal_coeditor_code                   ?
_journal_coeditor_notes                  ?
_journal_techeditor_code                 ? 
_journal_techeditor_notes                ?
_journal_coden_ASTM                      ? 
_journal_name_full                       ?
_journal_year                            ?
_journal_volume                          ?
_journal_issue                           ?
_journal_page_first                      ?
_journal_page_last                       ?
_journal_suppl_publ_number               ?
_journal_suppl_publ_pages                ?

#=======================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title
;

Structural analysis of the azo-enaminone
4-(E)-amino-3-[(E)-4-nitrophenylazo]-3-penten-2-one

;
loop_
_publ_author_name
_publ_author_address

    'Cunha, Silvio'
;    Instituto de Química - UFG 
     74001-970 - Goiânia, GO 
     Brazil
;
    'Farias, Maria de F.'
;    Instituto de Química - UFG 
     74001-970 - Goiânia, GO 
     Brazil
;    
    'Silva, Renata M.'
;    Instituto de Química - UFG 
     74001-970 - Goiânia, GO 
     Brazil
;    
    'Sá, Fernando P.'
;    Instituto de Física - UFG 
     74001-970 - Goiânia, GO 
     Brazil
;
    'Lariucci, Carlito'
;    Instituto de Física - UFG 
     74001-970 - Goiânia, GO 
     Brazil
;    
    'Vencato, Ivo'
;    Instituto de Física - UFG
     74001-970 - Goiânia, GO
     Brazil
;  
    'Silva, Cleuza C. da'
;    Departamento de Química - UEM
     Av. Colombo 5790
     87020-900 - Maringá, PR 
     Brazil
;
#=======================================================================

# 4. TEXT

_publ_section_abstract

; 

The title compound, C₁₁H₁₂N₄O₃, is planar to within
0.400 Å (excluding H atoms).


;

_publ_section_comment

;                
Although there are some X ray structural investigations involving
simple enaminones (Gilli, P. et al.,2000; Kubicki, M., Bassyouni, H. A. R.
& Codding, P. W., 2000; Dannhart, X. et al., 1998; Bertolasi, V. et
al.,1998), the structural analysis of azo-enaminones is scarce (Rodrigues,
B. L. et al., 1996; Kettmann, V. et al., 2001). Otherwise, understanding how
enaminones fit together in the solid state is of particular interest
because azo-enaminones are compounds with potential nonlinear optical
properties (Figueiredo, L. J. O. & Kascheres, C., 1997). Indeed,
azo-enaminones can exist in both hydrazoimino/azoenamine tautomeric forms
even in the solid state (Kettmann, V. et al., 2001). Thus we had prepared
the azo-enaminone 3 containing the NH₂H-bond donor group and the
NO₂H-bond acceptor group in the "head" and in the "tail" of the molecule,
respectively, and undertook its structural analysis.
A ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) plot of the molecule and 
the atomic numbering is shown in Fig. 1. Selected bond distances and 
angles are given in Table 1.

With regard to the tautomeric equilibrium, 3 exists only in the azoenamine
form in the solid state, as can be seen from bond lengths along
N3 N2 C3 C4 N1 which are in agreement with another previously
described azo-enaminone containing a primary amine (Figueiredo, L. J. O.
& Kascheres, C., 1997).

An intramolecular hydrogen bond is observed between N1-H2N...N3
[2.601(4)Å]. The atom N1 is -0.036(5) Å from the least-square plane
through the atoms N3 N2 C3 C4. Therefore, the intramolecular hydrogen bond
contributes to the planarity of this conjugated moiety of 3. Additionally,
the aromatic ring is almost coplanar with the enaminone moiety as
indicated by the C7-C6-N3-N2 torsion angle of -9.8(4)°.

The intermolecular packing of compound 3 occurs through a hydrogen-bonded
network (Figure 2). In this network, two dimensional head-to-tail
molecular orientated chains are observed, and one chain is involved
with another one through both intermolecular head-to-tail and head-to-head
H-bonds: N1-H1N...O1ⁱ [ x, -1/2-y, 1/2+z, 2.865(3) Å] and   
N1-H2N...O3ⁱⁱ [1-x, y-1/2, 1/2-z, 3.037(4) Å]. Contrary with the
previously described azo-enaminone containing the para-nitrophenyl group,
the presence of the nitro group at the aromatic ring of 3 is crucial to
the intermolecular H-bond network.

;
_publ_section_acknowledgements
;  
                                                                       
The authors thank the Conselho Nacional de Desenvolvimento 
Científico e Tecnológico - CNPq, for a felloship to
IV and FPS (PIBIC/CNPq/UFG) and also the Depto. Química - UFSC
for X-ray datacollection.


;
_publ_section_references

;

Bertolasi, V., Gilli, P., Ferretti, V.  and Gilli, G. (1998).
        Acta Cryst. B54, 50--65.

Figueiredo, L. J. O. & Kascheres, C. (1997). J. Org. Chem. 62,
        1164--1167.

Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (2000).
        J. Am. Chem. Soc. 122, 10405--10417.

Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf-Nonius,  
        Delft, The Netherlands.

Kettmann, V., Lokaj, J., Simunek, P. & Macháev, V. (2001). 
        Acta Cryst. C57, 737--739.

Kubicki, M., Bassyouni, H. A. R. & Codding, P. W. (2000).
        J. Mol. Struc. 525, 141--152.

Rodrigues, B. L., Gambardella, M. T. P., Figueiredo, L. J. O.
        & Kascheres, C. (1996). Acta Cryst. C52, 705--707.

Sheldrick, G. M. (1990). SHELXS97.  Program for the Solution of Crystal 
        Structures.  Univ. of Göttingen, Germany. 

Sheldrick, G. M. (1997). SHELXL97.  Program for the Refinement of 
        Crystal Structures. Univ. of Göttingen, Germany.

Spek, A. L. (1996). Program for Reduction of CAD-4 Data. University
        of Utrecht. The Netherlands.

Spek, A. L. (1998). PLATON. Program for the Analysis of Molecular
        Geometry. Version of January 1998. University of Utrecht,
        The Netherlands.

Zsolnai, L., Pritzkow, H. & Hutter, G. (1996). ZORTEP. University
        of Heidelberg, Germany.


;
_publ_section_figure_captions
;

Figure 1. The molecular structure of the title compound showing
          the numbering scheme. Displacement ellipsoids are drawn
          at the 30% probability level. The dashed line shows
          the intramolecular hydrogen bonding. The methyl H atoms
          are disordered and only one orientation is shown.

Figure 2. A stereopair illustrating the crystal packing. The structure
          is viewed along the b axis with the a axis horizontal.
          The intermolecular hydrogen bonds are shown as dashed lines.

;
_publ_section_table_legends
;

Table 1. Selected geometric parameters (Å, °).

;

_publ_section_exptl_prep
;
 
To a solution of 276.8 mg (2.0 mmol) of p-nitro-aniline in 1.2 mL of
6N HCl in  2.5 mL of water was added drop wise a solution 172.5 mg
(2.5 mmol) of NaNO₂ in 3 mL of water under vigorous magnetic
stirring and ice-bath cooling.  5 mg or urea was added and the
solution was neutralized by addition of Na₂CO₃. 15 mL of
CH₂Cl₂. The orange solid that formed was collected by filtration
and allowed to dry in air
to afford 224.1 mg (46 % yield) of azo-enaminones 3, mp 198-199 °C.
IR (KBr): 3448, 3185, 1636, 1584, 1510, 1311 cm⁻¹. ¹H
NMR (CD₃OD): δ 2.51 (3H, s); 2.53 (3H,s);7.67 (2H, d, J = 9.0 Hz);
8.22 (2H, d, J = 9.0 Hz). MS m/z (%): 249 (13.5) [ M⁺ +1],
248 (100) [M⁺], 231 (17), 216 (41), 205 (28), 151 950), 98 (62).

;

_publ_section_exptl_refinement
;

All the phenyl H atoms were placed in calculated positions using a
riding model [C-H = 0.93 Å, U(H) = 1.2Ueq(C) for C~sp²~]; the H atoms
of N1 were found by difference Fourier and refined with
U(H) = 1.2Ueq(N).
The final map showed all the H atoms of the C~sp³~ C1 and C5 atoms.
An attempt to refine them lead to an unaccepted geometry, even using
the SHELXL97 AFIX 33 or 137 instructions (Sheldrick, 1997) that
resulted in S greater than 1.2.
So we decided to place them as disordered atoms, using the command
AFIX 123 with C-H = 0.96Å and U(H) = 1.5Ueq(C).
Examination of the structure with PLATON (Spek, 1998) showed that
there were no solvent-accessible voids in the crystal lattice.
;

#=====================================================================
data_(I)

# 5. CHEMICAL DATA 

_chemical_name_systematic
;

α-haloketal, (1'R,4S,5S)-Dimethyl 2-(1'-bromoethyl)-2-
(3",4"-dimethoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate

;

# OBS: colocar o nome IUPAC

_chemical_name_common             azo-enaminones
_chemical_formula_moiety
 'C11 H12 N4 O3'
_chemical_formula_sum 
 'C11 H12 N4 O3' 
_chemical_formula_weight          248.25 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_melting_point          ' 198-199 K '
_chemical_compound_source        ?  
 
#=====================================================================

# 6. CRYSTAL DATA 

_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M   'P 1 21/c 1' 
_symmetry_space_group_name_Hall  '-P 2ybc'

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                    10.745(2) 
_cell_length_b                    8.670(2) 
_cell_length_c                    12.747(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.50(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1179.9(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min        8.46
_cell_measurement_theta_max       13.57 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             red 
_exptl_crystal_size_max           0.33 
_exptl_crystal_size_mid           0.30 
_exptl_crystal_size_min           0.16 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.398 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              520 
_exptl_absorpt_coefficient_mu     0.105 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 

_exptl_special_details 

;
 
 ? 
; 

#=====================================================================

# 7. EXPERIMENTAL DATA COLLECTION 

_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   'Nonius CAD-4 diffractometer' 
_diffrn_measurement_method        ω--2θ 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   60 
_diffrn_standards_decay_%         0.4 

_diffrn_reflns_number             2184
_diffrn_reflns_av_R_equivalents   0.0174 
_diffrn_reflns_av_sigmaI/netI     0.0315 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.85 
_diffrn_reflns_theta_max          25.07 
_reflns_number_total              2067 
_reflns_number_gt                 1409 
_reflns_threshold_expression      I>2σ(I) 

_computing_data_collection        'CAD-4 EXPRESS (Enraf-Nonius, 1994)' 
_computing_cell_refinement         
;
SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction         'HELENA   (Spek, 1996)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     
;
 ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) 
;
_computing_publication_material    
; 
SHELXL-97. All calculations were performed on a DEC 3000 AXP and 
PC/Pentium II computer running LINUX.
;

#=====================================================================

# 8. REFINEMENT DATA 

_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
 'w=1/[σ²(Fo²)+(0.0338P)²+0.9382P] where P=(Fo²+2Fc²)/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      SHELXL 
_refine_ls_extinction_coef        0.0126(18) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2067 
_refine_ls_number_parameters      170 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0811 
_refine_ls_R_factor_gt            0.0426 
_refine_ls_wR_factor_ref          0.1372 
_refine_ls_wR_factor_gt           0.0956 
_refine_ls_goodness_of_fit_ref    1.168 
_refine_ls_restrained_S_all       1.168 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 

_diffrn_measured_fraction_theta_max    0.917 
_diffrn_reflns_theta_full              25.07 
_diffrn_measured_fraction_theta_full   0.917 
_refine_diff_density_max    0.257 
_refine_diff_density_min   -0.213 
_refine_diff_density_rms    0.050 
 
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' 
 'O'  'O'   0.0106   0.0060 
 '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' 
 
#=====================================================================

# 9. ATOMIC  COORDINATES AND DISPLACEMENT PARAMETERS 
 
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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.0672(2) -0.2161(3) -0.19885(16) 0.0652(7) Uani 1 d . . . 
O2 O 0.7614(2) 0.5096(3) 0.01099(18) 0.0665(7) Uani 1 d . . . 
O3 O 0.7420(2) 0.5425(3) 0.17609(18) 0.0702(7) Uani 1 d . . . 
N1 N 0.1390(2) -0.1148(3) 0.12449(19) 0.0488(6) Uani 1 d . . . 
H1N H 0.099(3) -0.168(4) 0.176(2) 0.059 Uiso 1 d . . . 
H2N H 0.201(3) -0.045(4) 0.138(2) 0.059 Uiso 1 d . . . 
N2 N 0.2620(2) 0.0296(3) -0.03802(17) 0.0412(6) Uani 1 d . . . 
N3 N 0.3051(2) 0.0675(3) 0.05723(17) 0.0430(6) Uani 1 d . . . 
N4 N 0.7110(2) 0.4812(3) 0.0902(2) 0.0500(6) Uani 1 d . . . 
C1 C 0.1847(4) -0.0018(4) -0.2470(2) 0.0734(11) Uani 1 d . . . 
H1A H 0.1559 -0.0363 -0.3171 0.110 Uiso 0.50 calc PR . . 
H1B H 0.2746 -0.0039 -0.2368 0.110 Uiso 0.50 calc PR . . 
H1C H 0.1559 0.1015 -0.2375 0.110 Uiso 0.50 calc PR . . 
H1D H 0.2350 0.0772 -0.2105 0.110 Uiso 0.50 calc PR . . 
H1E H 0.1164 0.0448 -0.2908 0.110 Uiso 0.50 calc PR . . 
H1F H 0.2350 -0.0606 -0.2901 0.110 Uiso 0.50 calc PR . . 
C2 C 0.1340(3) -0.1066(4) -0.1679(2) 0.0477(7) Uani 1 d . . . 
C3 C 0.1669(2) -0.0742(3) -0.0551(2) 0.0397(6) Uani 1 d . . . 
C4 C 0.1052(2) -0.1482(3) 0.0247(2) 0.0408(6) Uani 1 d . . . 
C5 C 0.0011(3) -0.2620(3) 0.0031(2) 0.0497(7) Uani 1 d . . . 
H5A H -0.0255 -0.2961 0.0686 0.074 Uiso 0.50 calc PR . . 
H5B H 0.0299 -0.3488 -0.0342 0.074 Uiso 0.50 calc PR . . 
H5C H -0.0679 -0.2141 -0.0391 0.074 Uiso 0.50 calc PR . . 
H5D H -0.0168 -0.2766 -0.0718 0.074 Uiso 0.50 calc PR . . 
H5E H -0.0722 -0.2239 0.0310 0.074 Uiso 0.50 calc PR . . 
H5F H 0.0256 -0.3586 0.0360 0.074 Uiso 0.50 calc PR . . 
C6 C 0.4080(2) 0.1701(3) 0.0604(2) 0.0396(6) Uani 1 d . . . 
C7 C 0.4696(3) 0.2072(3) -0.0270(2) 0.0448(7) Uani 1 d . . . 
H7 H 0.4428 0.1640 -0.0924 0.054 Uiso 1 calc R . . 
C8 C 0.5697(3) 0.3072(3) -0.0169(2) 0.0445(7) Uani 1 d . . . 
H8 H 0.6111 0.3316 -0.0750 0.053 Uiso 1 calc R . . 
C9 C 0.6078(2) 0.3707(3) 0.0809(2) 0.0416(6) Uani 1 d . . . 
C10 C 0.5487(3) 0.3361(4) 0.1691(2) 0.0508(8) Uani 1 d . . . 
H10 H 0.5753 0.3804 0.2342 0.061 Uiso 1 calc R . . 
C11 C 0.4496(3) 0.2345(4) 0.1581(2) 0.0487(7) Uani 1 d . . . 
H11 H 0.4100 0.2085 0.2168 0.058 Uiso 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 0.0774(16) 0.0733(15) 0.0464(12) -0.0205(11) 0.0130(11) -0.0195(13) 
O2 0.0627(14) 0.0739(16) 0.0662(15) -0.0006(12) 0.0218(12) -0.0165(12) 
O3 0.0733(16) 0.0768(17) 0.0584(14) -0.0075(12) -0.0016(12) -0.0221(13) 
N1 0.0526(15) 0.0559(16) 0.0381(13) 0.0041(12) 0.0066(11) -0.0083(13) 
N2 0.0439(13) 0.0426(13) 0.0371(12) 0.0011(10) 0.0042(10) 0.0044(11) 
N3 0.0437(13) 0.0465(13) 0.0383(12) -0.0014(10) 0.0026(10) -0.0022(11) 
N4 0.0445(14) 0.0503(15) 0.0550(15) 0.0024(13) 0.0055(12) -0.0004(12) 
C1 0.099(3) 0.084(3) 0.0359(17) 0.0025(17) 0.0049(17) -0.019(2) 
C2 0.0497(16) 0.0528(18) 0.0410(15) -0.0031(14) 0.0078(13) 0.0042(15) 
C3 0.0419(15) 0.0417(15) 0.0353(14) -0.0030(12) 0.0041(11) 0.0012(12) 
C4 0.0398(14) 0.0410(15) 0.0420(15) -0.0003(12) 0.0063(12) 0.0066(12) 
C5 0.0490(16) 0.0496(17) 0.0507(16) 0.0000(14) 0.0071(13) -0.0019(14) 
C6 0.0401(14) 0.0380(14) 0.0407(14) 0.0029(12) 0.0039(11) 0.0046(12) 
C7 0.0476(16) 0.0498(17) 0.0371(14) -0.0002(13) 0.0050(12) 0.0026(14) 
C8 0.0436(15) 0.0502(17) 0.0406(15) 0.0030(13) 0.0089(12) 0.0051(13) 
C9 0.0379(14) 0.0387(15) 0.0479(15) 0.0021(12) 0.0035(12) 0.0015(12) 
C10 0.0540(18) 0.0592(19) 0.0387(15) -0.0046(14) 0.0033(13) -0.0063(15) 
C11 0.0535(17) 0.0586(19) 0.0350(14) 0.0025(13) 0.0089(12) -0.0041(15) 

#=====================================================================

# 10. MOLECULAR GEOMETRY 
 
_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 C2 1.228(4) . ? 
O2 N4 1.224(3) . ? 
O3 N4 1.229(3) . ? 
N1 C4 1.315(3) . yes 
N1 H1N 0.95(3) . ? 
N1 H2N 0.91(3) . ? 
N2 N3 1.292(3) . yes 
N2 C3 1.361(3) . yes 
N3 C6 1.416(3) . yes 
N4 C9 1.460(4) . ? 
C1 C2 1.504(4) . ? 
C1 H1A 0.9600 . ? 
C1 H1B 0.9600 . ? 
C1 H1C 0.9600 . ? 
C1 H1D 0.9600 . ? 
C1 H1E 0.9600 . ? 
C1 H1F 0.9600 . ? 
C2 C3 1.469(4) . ? 
C3 C4 1.428(4) . yes 
C4 C5 1.494(4) . ? 
C5 H5A 0.9600 . ? 
C5 H5B 0.9600 . ? 
C5 H5C 0.9600 . ? 
C5 H5D 0.9600 . ? 
C5 H5E 0.9600 . ? 
C5 H5F 0.9600 . ? 
C6 C11 1.391(4) . ? 
C6 C7 1.397(4) . ? 
C7 C8 1.376(4) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.381(4) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.386(4) . ? 
C10 C11 1.376(4) . ? 
C10 H10 0.9300 . ? 
C11 H11 0.9300 . ? 
 
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 
C4 N1 H1N 118.0(18) . . ? 
C4 N1 H2N 116.4(19) . . ? 
H1N N1 H2N 126(3) . . ? 
N3 N2 C3 120.1(2) . . yes 
N2 N3 C6 112.5(2) . . yes 
O2 N4 O3 123.2(3) . . ? 
O2 N4 C9 117.9(2) . . ? 
O3 N4 C9 118.9(2) . . ? 
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 . . ? 
C2 C1 H1D 109.5 . . ? 
H1A C1 H1D 141.1 . . ? 
H1B C1 H1D 56.3 . . ? 
H1C C1 H1D 56.3 . . ? 
C2 C1 H1E 109.5 . . ? 
H1A C1 H1E 56.3 . . ? 
H1B C1 H1E 141.1 . . ? 
H1C C1 H1E 56.3 . . ? 
H1D C1 H1E 109.5 . . ? 
C2 C1 H1F 109.5 . . ? 
H1A C1 H1F 56.3 . . ? 
H1B C1 H1F 56.3 . . ? 
H1C C1 H1F 141.1 . . ? 
H1D C1 H1F 109.5 . . ? 
H1E C1 H1F 109.5 . . ? 
O1 C2 C3 122.0(3) . . ? 
O1 C2 C1 119.6(3) . . ? 
C3 C2 C1 118.4(3) . . ? 
N2 C3 C4 125.8(2) . . yes 
N2 C3 C2 112.1(2) . . yes 
C4 C3 C2 122.2(3) . . yes 
N1 C4 C3 119.4(3) . . yes 
N1 C4 C5 116.3(3) . . yes 
C3 C4 C5 124.3(2) . . yes 
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 . . ? 
C4 C5 H5D 109.5 . . ? 
H5A C5 H5D 141.1 . . ? 
H5B C5 H5D 56.3 . . ? 
H5C C5 H5D 56.3 . . ? 
C4 C5 H5E 109.5 . . ? 
H5A C5 H5E 56.3 . . ? 
H5B C5 H5E 141.1 . . ? 
H5C C5 H5E 56.3 . . ? 
H5D C5 H5E 109.5 . . ? 
C4 C5 H5F 109.5 . . ? 
H5A C5 H5F 56.3 . . ? 
H5B C5 H5F 56.3 . . ? 
H5C C5 H5F 141.1 . . ? 
H5D C5 H5F 109.5 . . ? 
H5E C5 H5F 109.5 . . ? 
C11 C6 C7 119.2(3) . . ? 
C11 C6 N3 116.7(2) . . ? 
C7 C6 N3 124.1(2) . . ? 
C8 C7 C6 120.4(3) . . ? 
C8 C7 H7 119.8 . . ? 
C6 C7 H7 119.8 . . ? 
C7 C8 C9 118.9(3) . . ? 
C7 C8 H8 120.5 . . ? 
C9 C8 H8 120.5 . . ? 
C8 C9 C10 122.0(3) . . ? 
C8 C9 N4 118.7(2) . . ? 
C10 C9 N4 119.3(3) . . ? 
C11 C10 C9 118.4(3) . . ? 
C11 C10 H10 120.8 . . ? 
C9 C10 H10 120.8 . . ? 
C10 C11 C6 121.0(3) . . ? 
C10 C11 H11 119.5 . . ? 
C6 C11 H11 119.5 . . ? 
 
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 
C3 N2 N3 C6 176.8(2) . . . . ? 
N3 N2 C3 C4 0.9(4) . . . . ? 
N3 N2 C3 C2 -178.0(2) . . . . ? 
O1 C2 C3 N2 166.6(3) . . . . ? 
C1 C2 C3 N2 -13.2(4) . . . . ? 
O1 C2 C3 C4 -12.3(4) . . . . ? 
C1 C2 C3 C4 167.9(3) . . . . ? 
N2 C3 C4 N1 1.1(4) . . . . ? 
C2 C3 C4 N1 179.8(3) . . . . ? 
N2 C3 C4 C5 -179.9(3) . . . . ? 
C2 C3 C4 C5 -1.1(4) . . . . ? 
N2 N3 C6 C11 171.3(2) . . . . ? 
N2 N3 C6 C7 -9.8(4) . . . . ? 
C11 C6 C7 C8 -0.6(4) . . . . ? 
N3 C6 C7 C8 -179.4(3) . . . . ? 
C6 C7 C8 C9 -0.3(4) . . . . ? 
C7 C8 C9 C10 0.4(4) . . . . ? 
C7 C8 C9 N4 -177.7(2) . . . . ? 
O2 N4 C9 C8 -1.9(4) . . . . ? 
O3 N4 C9 C8 177.2(3) . . . . ? 
O2 N4 C9 C10 180.0(3) . . . . ? 
O3 N4 C9 C10 -0.9(4) . . . . ? 
C8 C9 C10 C11 0.4(4) . . . . ? 
N4 C9 C10 C11 178.4(3) . . . . ? 
C9 C10 C11 C6 -1.2(4) . . . . ? 
C7 C6 C11 C10 1.3(4) . . . . ? 
N3 C6 C11 C10 -179.7(3) . . . . ? 
 
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 H2N N3  0.91(3) 1.87(3) 2.601(4) 136(3) . 
N1 H1N O1  0.95(3) 1.95(3) 2.865(3) 163(3) 4_556 
N1 H2N O3  0.91(3) 2.50(3) 3.037(4) 118(2) 2_645 
 
