# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2004


data_global

_journal_coden_Cambridge         440

loop_
_publ_author_name
'Ibon Alkorta'
'Carmen Alvarez-Rua'
'R. M. Claramunt'
'Swapan Dey'
'Jose Elguero'
'Santiago Garcia-granda'
'Shyamaprosad Goswami'
'Nadine Jagerovic'
'M Dolores Santa Maria'
'Reshmi Mukherjee'
'Isabel Rozas'

_publ_contact_author_name        'Dr Ibon Alkorta'
_publ_contact_author_address     
;
I.Q.M
CSIC
Juan de la Cierva, 3
Madrid
28006
SPAIN
;

_publ_contact_author_email       IBON@IQM.CSIC.ES

_publ_requested_journal          'New Journal of Chemistry'

_publ_section_title              
;
Multiple hydrogen bonds and tautomerism in
naphthyridine derivatives
;

# 4. text
_publ_section_exptl_prep         
;
data collection was performed on a nonius kappaccd
single crystal diffractometer.
crystal-detector distance was fixed at 29 mm, and a total of 1315 images were
collected using the oscillation method, with 1.2\% oscillation and 30 s exposure
time per image. final mosaicity was 0.414(2)\%.
all data completeness was 98.4%.
intensity-error ratio for all reflections was 122.3 : 8.5.
;
_publ_section_exptl_refinement   
;
crystal structure was solved by direct methods.
all non-hydrogen atoms were anisotropically refined.
hydrogen atoms were located in difference fourier maps.
geometrical calculations made with parst97 (nardelli, 1995).
all calculations were made at the university of oviedo on the x-ray group
computers.
;
_publ_section_references         
;
blessing, r. h. (1995). acta cryst. a51, 33-38.
nardelli, m. (1995). j. appl. cryst. 28, 659.
nonius bv, (1997-2000). collect.
otwinowski, z. & minor, w. (1997). methods enzymol. 276, 307-326.
sheldrick, g. m. (1990). acta cryst. a46, 467-473.
sheldrick, g. m. (1997). shelxl-97. university of gottingen. a computer
program for refinement of crystal structures.
spek, a. l. (2001). platon. a multipurpose crystallographic tool, utrecht
university, utrecht, the netherlands.
;
#==================================================================
#============
data_4a
_database_code_depnum_ccdc_archive 'CCDC 236718'
#==================================================================
#============
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         '2(C12 H12 N4 O2), H2 O'
_chemical_formula_sum            'C24 H26 N8 O5'
_chemical_formula_weight         506.53
_chemical_compound_source        synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 21/c'
_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                   27.8630(5)
_cell_length_b                   11.4857(2)
_cell_length_c                   7.5182(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.915(1)
_cell_angle_gamma                90.00
_cell_volume                     2400.41(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    18703
_cell_measurement_theta_min      1.767
_cell_measurement_theta_max      70.076

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.846

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995) '
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.955

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26311
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         69.85
_reflns_number_total             4481
_reflns_number_gt                2970
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4481
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.19409(7) 0.65308(18) 0.3686(3) 0.0422(5) Uani 1 d . . .
H11A H 0.1996(10) 0.582(2) 0.339(4) 0.046(8) Uiso 1 d . . .
N2A N 0.27575(7) 0.65455(16) 0.3651(3) 0.0370(5) Uani 1 d . . .
N3A N 0.35754(6) 0.64236(16) 0.3439(2) 0.0346(4) Uani 1 d . . .
N4A N 0.43769(7) 0.61641(18) 0.3143(3) 0.0374(5) Uani 1 d . . .
H44A H 0.4258(11) 0.541(3) 0.267(4) 0.071(9) Uiso 1 d . . .
O1A O 0.13742(7) 0.79431(18) 0.3840(4) 0.0900(9) Uani 1 d . . .
O2A O 0.50394(7) 0.73234(17) 0.3610(3) 0.0630(6) Uani 1 d . . .
C1A C 0.11042(10) 0.6003(2) 0.3772(5) 0.0585(8) Uani 1 d . . .
H1A H 0.1227 0.5278 0.3288 0.088 Uiso 1 calc R . .
H1B H 0.0818 0.6254 0.3041 0.088 Uiso 1 calc R . .
H1C H 0.1019 0.5873 0.5000 0.088 Uiso 1 calc R . .
C2A C 0.14792(9) 0.6916(2) 0.3751(4) 0.0486(6) Uani 1 d . . .
C3A C 0.23676(8) 0.7178(2) 0.3847(3) 0.0377(5) Uani 1 d . . .
C4A C 0.23736(10) 0.8391(2) 0.4230(3) 0.0421(6) Uani 1 d . . .
H4A H 0.2085(10) 0.875(2) 0.445(4) 0.061(9) Uiso 1 d . . .
C5A C 0.28090(9) 0.8931(2) 0.4365(3) 0.0428(6) Uani 1 d . . .
H5A H 0.2828(9) 0.977(2) 0.475(4) 0.052(8) Uiso 1 d . . .
C6A C 0.32310(9) 0.8315(2) 0.4082(3) 0.0365(5) Uani 1 d . . .
C7A C 0.36941(9) 0.8799(2) 0.4153(3) 0.0410(6) Uani 1 d . . .
H7A H 0.3735(10) 0.963(2) 0.443(4) 0.056(8) Uiso 1 d . . .
C8A C 0.40823(9) 0.8125(2) 0.3869(3) 0.0414(6) Uani 1 d . . .
H8A H 0.4408(10) 0.843(2) 0.385(3) 0.047(7) Uiso 1 d . . .
C9A C 0.40015(8) 0.6929(2) 0.3507(3) 0.0348(5) Uani 1 d . . .
C10A C 0.31889(8) 0.71083(19) 0.3726(3) 0.0339(5) Uani 1 d . . .
C11A C 0.48562(9) 0.6396(2) 0.3141(3) 0.0442(6) Uani 1 d . . .
C12A C 0.51501(9) 0.5410(3) 0.2516(4) 0.0544(7) Uani 1 d . . .
H12A H 0.4939 0.4751 0.2183 0.082 Uiso 1 calc R . .
H12B H 0.5386 0.5172 0.3475 0.082 Uiso 1 calc R . .
H12C H 0.5319 0.5658 0.1478 0.082 Uiso 1 calc R . .
N1B N 0.07812(7) 0.50225(19) -0.1071(3) 0.0422(5) Uani 1 d . . .
H11B H 0.0944(10) 0.571(3) -0.102(4) 0.061(9) Uiso 1 d . . .
N2B N 0.14602(6) 0.44386(16) 0.0525(3) 0.0372(5) Uani 1 d . . .
N3B N 0.21597(7) 0.40135(15) 0.2177(3) 0.0349(4) Uani 1 d . . .
N4B N 0.28732(7) 0.37475(18) 0.3776(3) 0.0374(5) Uani 1 d . . .
H44B H 0.2866(11) 0.460(3) 0.379(4) 0.076(10) Uiso 1 d . . .
O1B O 0.01005(7) 0.41272(19) -0.2199(4) 0.0778(7) Uani 1 d . . .
O2B O 0.32799(6) 0.21386(15) 0.4863(2) 0.0491(5) Uani 1 d . . .
C1B C 0.01572(10) 0.6172(3) -0.2604(4) 0.0571(7) Uani 1 d . . .
H1D H 0.0420 0.6739 -0.2467 0.086 Uiso 1 calc R . .
H1E H -0.0108 0.6425 -0.1905 0.086 Uiso 1 calc R . .
H1F H 0.0044 0.6117 -0.3864 0.086 Uiso 1 calc R . .
C2B C 0.03335(9) 0.5008(2) -0.1956(4) 0.0494(6) Uani 1 d . . .
C3B C 0.10445(8) 0.4106(2) -0.0278(3) 0.0371(5) Uani 1 d . . .
C4B C 0.08792(8) 0.2938(2) -0.0343(3) 0.0399(5) Uani 1 d . . .
H4B H 0.0549(11) 0.273(3) -0.089(4) 0.067(9) Uiso 1 d . . .
C5B C 0.11817(9) 0.2107(2) 0.0393(3) 0.0413(6) Uani 1 d . . .
H5B H 0.1065(9) 0.127(2) 0.040(4) 0.054(8) Uiso 1 d . . .
C6B C 0.16360(8) 0.24095(19) 0.1198(3) 0.0350(5) Uani 1 d . . .
C7B C 0.19812(9) 0.1619(2) 0.1938(3) 0.0398(5) Uani 1 d . . .
H7B H 0.1907(9) 0.076(2) 0.190(4) 0.052(8) Uiso 1 d . . .
C8B C 0.23990(9) 0.2019(2) 0.2745(3) 0.0399(5) Uani 1 d . . .
H8B H 0.2635(9) 0.151(2) 0.326(4) 0.051(8) Uiso 1 d . . .
C9B C 0.24717(8) 0.32407(19) 0.2865(3) 0.0351(5) Uani 1 d . . .
C10B C 0.17496(8) 0.36066(19) 0.1290(3) 0.0339(5) Uani 1 d . . .
C11B C 0.32374(8) 0.3202(2) 0.4765(3) 0.0395(5) Uani 1 d . . .
C12B C 0.35897(10) 0.3994(2) 0.5736(4) 0.0509(7) Uani 1 d . . .
H12D H 0.3457 0.4784 0.5748 0.076 Uiso 1 calc R . .
H12E H 0.3891 0.3999 0.5134 0.076 Uiso 1 calc R . .
H12F H 0.3653 0.3718 0.6963 0.076 Uiso 1 calc R . .
O10 O 0.41465(7) 0.38014(16) 0.1663(3) 0.0594(6) Uani 1 d G . .
H10A H 0.4369 0.3216 0.1690 0.072(10) Uiso 1 d G . .
H10B H 0.3881 0.3487 0.1194 0.076(11) Uiso 1 d G . .

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
N1A 0.0358(11) 0.0338(11) 0.0566(13) -0.0082(9) 0.0004(9) 0.0037(9)
N2A 0.0341(10) 0.0337(10) 0.0426(11) -0.0035(8) -0.0016(8) -0.0002(8)
N3A 0.0312(10) 0.0349(10) 0.0371(10) -0.0030(8) -0.0018(8) -0.0027(8)
N4A 0.0310(10) 0.0414(11) 0.0392(11) -0.0025(9) -0.0029(8) -0.0040(9)
O1A 0.0411(12) 0.0479(12) 0.178(3) -0.0321(15) -0.0134(14) 0.0135(10)
O2A 0.0423(11) 0.0553(12) 0.0906(16) -0.0128(11) -0.0003(10) -0.0143(9)
C1A 0.0401(15) 0.0512(16) 0.086(2) -0.0112(15) 0.0145(14) 0.0008(12)
C2A 0.0411(14) 0.0440(14) 0.0600(16) -0.0098(12) -0.0027(12) 0.0058(12)
C3A 0.0406(13) 0.0340(12) 0.0379(12) -0.0035(9) -0.0029(10) 0.0021(10)
C4A 0.0475(14) 0.0369(13) 0.0414(14) -0.0033(10) 0.0003(11) 0.0064(11)
C5A 0.0516(15) 0.0308(12) 0.0459(14) -0.0058(10) 0.0022(11) -0.0005(10)
C6A 0.0452(13) 0.0332(12) 0.0308(11) 0.0000(9) -0.0009(9) -0.0024(10)
C7A 0.0503(15) 0.0320(12) 0.0405(13) -0.0010(10) 0.0012(10) -0.0079(11)
C8A 0.0471(14) 0.0374(12) 0.0394(13) -0.0006(10) 0.0015(11) -0.0093(11)
C9A 0.0351(12) 0.0379(12) 0.0307(11) 0.0006(9) -0.0018(9) -0.0039(10)
C10A 0.0366(12) 0.0329(12) 0.0316(11) -0.0003(9) -0.0024(9) -0.0022(9)
C11A 0.0366(13) 0.0485(14) 0.0466(14) 0.0003(11) -0.0039(11) -0.0094(11)
C12A 0.0366(14) 0.0587(17) 0.0677(18) -0.0060(14) 0.0025(13) -0.0021(12)
N1B 0.0301(11) 0.0401(11) 0.0553(13) 0.0024(9) -0.0045(9) -0.0016(9)
N2B 0.0283(9) 0.0343(10) 0.0485(11) -0.0015(8) -0.0006(8) -0.0002(8)
N3B 0.0308(10) 0.0311(10) 0.0425(11) 0.0011(8) 0.0003(8) -0.0011(8)
N4B 0.0341(10) 0.0343(10) 0.0432(11) 0.0017(8) -0.0023(8) -0.0003(8)
O1B 0.0498(13) 0.0578(13) 0.120(2) 0.0024(13) -0.0348(13) -0.0088(10)
O2B 0.0468(10) 0.0390(10) 0.0594(11) 0.0053(8) -0.0109(8) 0.0040(8)
C1B 0.0419(15) 0.0630(18) 0.0652(19) 0.0057(15) -0.0046(13) 0.0092(13)
C2B 0.0321(13) 0.0524(15) 0.0629(17) -0.0020(13) -0.0026(12) 0.0007(11)
C3B 0.0304(11) 0.0374(12) 0.0435(13) 0.0010(10) 0.0025(9) -0.0019(9)
C4B 0.0313(12) 0.0426(13) 0.0454(13) -0.0023(10) -0.0012(10) -0.0082(10)
C5B 0.0447(14) 0.0368(13) 0.0422(13) -0.0024(10) 0.0016(10) -0.0097(11)
C6B 0.0386(12) 0.0307(11) 0.0359(11) -0.0018(9) 0.0031(9) -0.0052(9)
C7B 0.0489(14) 0.0306(12) 0.0400(13) 0.0011(10) 0.0042(10) -0.0019(10)
C8B 0.0465(14) 0.0310(12) 0.0416(13) 0.0019(10) -0.0006(11) 0.0022(11)
C9B 0.0354(12) 0.0335(11) 0.0362(12) 0.0006(9) 0.0022(9) -0.0014(10)
C10B 0.0299(11) 0.0314(11) 0.0409(12) -0.0013(9) 0.0057(9) -0.0018(9)
C11B 0.0383(13) 0.0421(13) 0.0378(13) 0.0040(10) -0.0003(10) 0.0012(10)
C12B 0.0504(16) 0.0480(15) 0.0520(16) 0.0073(12) -0.0138(12) -0.0071(12)
O10 0.0382(10) 0.0421(10) 0.0957(16) -0.0108(10) -0.0104(10) 0.0028(9)

_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
N1A C2A 1.364(3) . ?
N1A C3A 1.400(3) . ?
N1A H11A 0.86(3) . ?
N2A C3A 1.323(3) . ?
N2A C10A 1.363(3) . ?
N3A C9A 1.319(3) . ?
N3A C10A 1.362(3) . ?
N4A C11A 1.362(3) . ?
N4A C9A 1.407(3) . ?
N4A H44A 0.99(3) . ?
O1A C2A 1.219(3) . ?
O2A C11A 1.223(3) . ?
C1A C2A 1.481(4) . ?
C1A H1A 0.9800 . ?
C1A H1B 0.9800 . ?
C1A H1C 0.9800 . ?
C3A C4A 1.423(3) . ?
C4A C5A 1.360(4) . ?
C4A H4A 0.93(3) . ?
C5A C6A 1.401(3) . ?
C5A H5A 1.01(3) . ?
C6A C7A 1.403(3) . ?
C6A C10A 1.415(3) . ?
C7A C8A 1.359(4) . ?
C7A H7A 0.98(3) . ?
C8A C9A 1.416(3) . ?
C8A H8A 0.97(3) . ?
C11A C12A 1.493(4) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
N1B C2B 1.373(3) . ?
N1B C3B 1.394(3) . ?
N1B H11B 0.91(3) . ?
N2B C3B 1.325(3) . ?
N2B C10B 1.353(3) . ?
N3B C9B 1.323(3) . ?
N3B C10B 1.365(3) . ?
N4B C11B 1.368(3) . ?
N4B C9B 1.398(3) . ?
N4B H44B 0.98(3) . ?
O1B C2B 1.209(3) . ?
O2B C11B 1.228(3) . ?
C1B C2B 1.495(4) . ?
C1B H1D 0.9800 . ?
C1B H1E 0.9800 . ?
C1B H1F 0.9800 . ?
C3B C4B 1.418(3) . ?
C4B C5B 1.365(3) . ?
C4B H4B 1.01(3) . ?
C5B C6B 1.409(3) . ?
C5B H5B 1.02(3) . ?
C6B C7B 1.409(3) . ?
C6B C10B 1.412(3) . ?
C7B C8B 1.355(3) . ?
C7B H7B 1.01(3) . ?
C8B C9B 1.420(3) . ?
C8B H8B 0.94(3) . ?
C11B C12B 1.492(3) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
O10 H10A 0.9142 . ?
O10 H10B 0.8761 . ?

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
C2A N1A C3A 128.5(2) . . ?
C2A N1A H11A 120.1(18) . . ?
C3A N1A H11A 111.0(18) . . ?
C3A N2A C10A 117.6(2) . . ?
C9A N3A C10A 117.32(19) . . ?
C11A N4A C9A 128.3(2) . . ?
C11A N4A H44A 118.5(18) . . ?
C9A N4A H44A 112.5(18) . . ?
C2A C1A H1A 109.5 . . ?
C2A C1A H1B 109.5 . . ?
H1A C1A H1B 109.5 . . ?
C2A C1A H1C 109.5 . . ?
H1A C1A H1C 109.5 . . ?
H1B C1A H1C 109.5 . . ?
O1A C2A N1A 123.1(3) . . ?
O1A C2A C1A 120.8(2) . . ?
N1A C2A C1A 116.0(2) . . ?
N2A C3A N1A 113.5(2) . . ?
N2A C3A C4A 124.2(2) . . ?
N1A C3A C4A 122.4(2) . . ?
C5A C4A C3A 117.4(2) . . ?
C5A C4A H4A 124.2(18) . . ?
C3A C4A H4A 118.3(18) . . ?
C4A C5A C6A 120.8(2) . . ?
C4A C5A H5A 119.1(15) . . ?
C6A C5A H5A 119.9(15) . . ?
C5A C6A C7A 125.0(2) . . ?
C5A C6A C10A 117.6(2) . . ?
C7A C6A C10A 117.4(2) . . ?
C8A C7A C6A 120.5(2) . . ?
C8A C7A H7A 120.4(17) . . ?
C6A C7A H7A 119.1(17) . . ?
C7A C8A C9A 117.7(2) . . ?
C7A C8A H8A 123.6(15) . . ?
C9A C8A H8A 118.6(15) . . ?
N3A C9A N4A 113.4(2) . . ?
N3A C9A C8A 124.4(2) . . ?
N4A C9A C8A 122.2(2) . . ?
N3A C10A N2A 115.10(19) . . ?
N3A C10A C6A 122.6(2) . . ?
N2A C10A C6A 122.3(2) . . ?
O2A C11A N4A 124.1(3) . . ?
O2A C11A C12A 121.7(2) . . ?
N4A C11A C12A 114.3(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C2B N1B C3B 129.2(2) . . ?
C2B N1B H11B 117.8(19) . . ?
C3B N1B H11B 113.0(19) . . ?
C3B N2B C10B 117.82(19) . . ?
C9B N3B C10B 117.84(19) . . ?
C11B N4B C9B 127.9(2) . . ?
C11B N4B H44B 117.9(18) . . ?
C9B N4B H44B 113.8(18) . . ?
C2B C1B H1D 109.5 . . ?
C2B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
C2B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
O1B C2B N1B 123.0(3) . . ?
O1B C2B C1B 122.6(2) . . ?
N1B C2B C1B 114.5(2) . . ?
N2B C3B N1B 113.3(2) . . ?
N2B C3B C4B 124.1(2) . . ?
N1B C3B C4B 122.7(2) . . ?
C5B C4B C3B 117.2(2) . . ?
C5B C4B H4B 121.1(17) . . ?
C3B C4B H4B 121.7(17) . . ?
C4B C5B C6B 120.9(2) . . ?
C4B C5B H5B 118.3(15) . . ?
C6B C5B H5B 120.8(15) . . ?
C7B C6B C5B 125.4(2) . . ?
C7B C6B C10B 117.6(2) . . ?
C5B C6B C10B 117.0(2) . . ?
C8B C7B C6B 120.0(2) . . ?
C8B C7B H7B 120.9(15) . . ?
C6B C7B H7B 119.1(15) . . ?
C7B C8B C9B 118.5(2) . . ?
C7B C8B H8B 121.7(16) . . ?
C9B C8B H8B 119.8(16) . . ?
N3B C9B N4B 113.24(19) . . ?
N3B C9B C8B 123.5(2) . . ?
N4B C9B C8B 123.3(2) . . ?
N2B C10B N3B 114.86(19) . . ?
N2B C10B C6B 122.8(2) . . ?
N3B C10B C6B 122.3(2) . . ?
O2B C11B N4B 123.6(2) . . ?
O2B C11B C12B 121.3(2) . . ?
N4B C11B C12B 115.2(2) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
H10A O10 H10B 105.0 . . ?

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
C3A N1A C2A O1A 5.5(5) . . . . ?
C3A N1A C2A C1A -172.4(3) . . . . ?
C10A N2A C3A N1A 177.8(2) . . . . ?
C10A N2A C3A C4A -3.7(3) . . . . ?
C2A N1A C3A N2A -177.4(2) . . . . ?
C2A N1A C3A C4A 4.1(4) . . . . ?
N2A C3A C4A C5A 1.4(4) . . . . ?
N1A C3A C4A C5A 179.7(2) . . . . ?
C3A C4A C5A C6A 1.9(4) . . . . ?
C4A C5A C6A C7A 178.6(2) . . . . ?
C4A C5A C6A C10A -2.5(3) . . . . ?
C5A C6A C7A C8A 179.6(2) . . . . ?
C10A C6A C7A C8A 0.7(3) . . . . ?
C6A C7A C8A C9A -0.1(3) . . . . ?
C10A N3A C9A N4A -178.21(18) . . . . ?
C10A N3A C9A C8A 0.5(3) . . . . ?
C11A N4A C9A N3A -178.4(2) . . . . ?
C11A N4A C9A C8A 2.8(4) . . . . ?
C7A C8A C9A N3A -0.5(3) . . . . ?
C7A C8A C9A N4A 178.1(2) . . . . ?
C9A N3A C10A N2A -179.70(19) . . . . ?
C9A N3A C10A C6A 0.1(3) . . . . ?
C3A N2A C10A N3A -177.3(2) . . . . ?
C3A N2A C10A C6A 2.9(3) . . . . ?
C5A C6A C10A N3A -179.7(2) . . . . ?
C7A C6A C10A N3A -0.7(3) . . . . ?
C5A C6A C10A N2A 0.1(3) . . . . ?
C7A C6A C10A N2A 179.1(2) . . . . ?
C9A N4A C11A O2A 6.1(4) . . . . ?
C9A N4A C11A C12A -174.1(2) . . . . ?
C3B N1B C2B O1B -1.5(5) . . . . ?
C3B N1B C2B C1B 178.7(2) . . . . ?
C10B N2B C3B N1B -178.0(2) . . . . ?
C10B N2B C3B C4B 1.8(4) . . . . ?
C2B N1B C3B N2B -177.6(3) . . . . ?
C2B N1B C3B C4B 2.6(4) . . . . ?
N2B C3B C4B C5B -3.6(4) . . . . ?
N1B C3B C4B C5B 176.2(2) . . . . ?
C3B C4B C5B C6B 0.8(4) . . . . ?
C4B C5B C6B C7B -177.7(2) . . . . ?
C4B C5B C6B C10B 3.3(4) . . . . ?
C5B C6B C7B C8B -177.3(2) . . . . ?
C10B C6B C7B C8B 1.7(4) . . . . ?
C6B C7B C8B C9B 1.7(4) . . . . ?
C10B N3B C9B N4B -178.7(2) . . . . ?
C10B N3B C9B C8B -0.7(3) . . . . ?
C11B N4B C9B N3B 173.7(2) . . . . ?
C11B N4B C9B C8B -4.3(4) . . . . ?
C7B C8B C9B N3B -2.4(4) . . . . ?
C7B C8B C9B N4B 175.4(2) . . . . ?
C3B N2B C10B N3B -176.6(2) . . . . ?
C3B N2B C10B C6B 2.8(4) . . . . ?
C9B N3B C10B N2B -176.1(2) . . . . ?
C9B N3B C10B C6B 4.5(3) . . . . ?
C7B C6B C10B N2B 175.6(2) . . . . ?
C5B C6B C10B N2B -5.3(4) . . . . ?
C7B C6B C10B N3B -5.0(4) . . . . ?
C5B C6B C10B N3B 174.1(2) . . . . ?
C9B N4B C11B O2B 6.5(4) . . . . ?
C9B N4B C11B C12B -173.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1A H11A N3B 1_555 0.86(3) 2.32(3) 3.180(3) 171(2) yes
N4A H44A O10 1_555 0.98(3) 2.01(3) 2.986(3) 169(3) yes
N4B H44B N2A 1_555 0.98(3) 2.23(3) 3.231(3) 173(3) yes
N1B H11B O1A 4_575 0.91(3) 1.97(3) 2.865(3) 170(2) yes
O10 H10A O2A 2_645 0.914 1.967 2.852(3) 162.4(1) yes
O10 H10B O2B 4_565 0.876 2.023 2.895(3) 173.6(1) yes
C4A H4A O1A . 0.93(3) 2.21(3) 2.827(3) 124(2) yes
C4B H4B O1B . 1.01(3) 2.22(3) 2.847(3) 119(3) yes
C8A H8A O2A . 0.97(3) 2.19(3) 2.840(3) 123(2) yes
C8B H8B O2B . 0.94(3) 2.22(3) 2.836(3) 123(2) yes

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        69.85
_diffrn_measured_fraction_theta_full 0.938
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.07
#==END
#==================================================================
#============
data_3a
_database_code_depnum_ccdc_archive 'CCDC 236719'
#==================================================================
#============

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N4 O'
_chemical_formula_sum            'C10 H10 N4 O'
_chemical_formula_weight         202.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
1/4-x,1/4+y,1/4+z
3/4+x,3/4-y,1/4+z
x,1/2+y,1/2+z
-x,1/2-y,1/2+z
1/4-x,3/4+y,3/4+z
3/4+x,1/4-y,3/4+z
1/2+x,y,1/2+z
1/2-x,-y,1/2+z
3/4-x,1/4+y,3/4+z
1/4+x,3/4-y,3/4+z
1/2+x,1/2+y,z
1/2-x,1/2-y,z
3/4-x,3/4+y,1/4+z
1/4+x,1/4-y,1/4+z

_cell_length_a                   19.001(3)
_cell_length_b                   25.829(8)
_cell_length_c                   7.844(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3849.7(17)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1432
_cell_measurement_theta_min      5.78
_cell_measurement_theta_max      68.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2690
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.78
_diffrn_reflns_theta_max         68.14
_reflns_number_total             1431
_reflns_number_gt                938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^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    mixed
_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   0.5(6)
_refine_ls_number_reflns         1431
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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
N2 N 0.02441(19) 0.19096(12) 0.2541(4) 0.0514(10) Uani 1 1 d . . .
C6 C -0.0010(4) 0.10878(11) 0.1213(6) 0.0558(8) Uani 1 1 d . . .
C3 C 0.0498(3) 0.16476(18) 0.3879(5) 0.0525(13) Uani 1 1 d . . .
N3 N -0.02820(18) 0.19240(13) -0.0096(4) 0.0513(11) Uani 1 1 d . . .
N4 N -0.0795(2) 0.19521(18) -0.2761(5) 0.0689(12) Uani 1 1 d . . .
C10 C -0.0018(4) 0.16337(11) 0.1208(6) 0.0501(8) Uani 1 1 d . . .
C8 C -0.0562(3) 0.11198(19) -0.1527(6) 0.0694(15) Uani 1 1 d . . .
H8 H -0.0754 0.0955 -0.2473 0.083 Uiso 1 1 calc R . .
C4 C 0.0524(3) 0.11109(18) 0.3967(5) 0.0599(13) Uani 1 1 d . . .
H4 H 0.0710 0.0945 0.4918 0.072 Uiso 1 1 calc R . .
O1 O 0.11980(17) 0.13983(12) 0.7078(4) 0.0771(9) Uani 1 1 d . . .
C5 C 0.0269(3) 0.08327(17) 0.2619(6) 0.0659(14) Uani 1 1 d . . .
H5 H 0.0283 0.0473 0.2642 0.079 Uiso 1 1 calc R . .
N1 N 0.0736(2) 0.19774(15) 0.5187(4) 0.0577(10) Uani 1 1 d . . .
H1 H 0.0673 0.2304 0.5029 0.069 Uiso 1 1 calc R . .
C7 C -0.0309(3) 0.08458(17) -0.0239(6) 0.0698(16) Uani 1 1 d . . .
H7 H -0.0328 0.0486 -0.0288 0.084 Uiso 1 1 calc R . .
C2 C 0.1054(3) 0.18394(19) 0.6673(5) 0.0629(13) Uani 1 1 d . . .
C9 C -0.0537(3) 0.16743(17) -0.1445(5) 0.0547(13) Uani 1 1 d . . .
C1 C 0.1247(2) 0.22980(16) 0.7785(5) 0.0693(12) Uani 1 1 d . . .
H1A H 0.1091 0.2612 0.7249 0.104 Uiso 1 1 calc R . .
H1B H 0.1748 0.2309 0.7935 0.104 Uiso 1 1 calc R . .
H1C H 0.1023 0.2263 0.8877 0.104 Uiso 1 1 calc R . .
H4B H -0.058(3) 0.229(2) -0.290(6) 0.104 Uiso 1 1 d . . .
H4A H -0.099(4) 0.179(2) -0.366(7) 0.104 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.060(3) 0.047(2) 0.0470(18) 0.000(2) -0.0022(15) -0.0007(19)
C6 0.063(2) 0.0476(18) 0.0568(19) -0.002(3) 0.0023(16) 0.000(3)
C3 0.050(3) 0.057(3) 0.050(2) -0.001(2) 0.000(2) 0.004(2)
N3 0.058(3) 0.050(2) 0.0463(19) -0.004(2) 0.0051(16) -0.0046(19)
N4 0.088(3) 0.070(3) 0.0484(19) 0.000(2) -0.009(2) -0.010(3)
C10 0.060(2) 0.0425(17) 0.0481(17) -0.002(3) 0.0025(15) -0.004(3)
C8 0.086(4) 0.057(4) 0.065(3) -0.012(3) -0.008(3) -0.001(3)
C4 0.071(4) 0.047(3) 0.063(3) 0.007(2) -0.005(2) 0.009(3)
O1 0.097(2) 0.065(2) 0.0695(17) 0.0115(14) -0.0140(17) 0.014(2)
C5 0.075(4) 0.048(3) 0.074(3) -0.009(3) 0.002(2) 0.004(2)
N1 0.070(3) 0.052(2) 0.0509(18) 0.0056(18) -0.0100(18) 0.004(2)
C7 0.088(5) 0.045(3) 0.076(3) -0.014(3) -0.003(3) -0.007(3)
C2 0.066(3) 0.064(3) 0.060(3) 0.006(2) 0.002(2) 0.010(2)
C9 0.061(4) 0.054(3) 0.049(3) -0.004(2) 0.009(2) -0.002(3)
C1 0.079(3) 0.071(3) 0.058(2) 0.004(2) -0.010(2) -0.005(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
N2 C3 1.339(5) . ?
N2 C10 1.360(5) . ?
C6 C5 1.390(7) . ?
C6 C10 1.410(4) . ?
C6 C7 1.419(7) . ?
C3 C4 1.389(6) . ?
C3 N1 1.408(6) . ?
N3 C9 1.330(5) . ?
N3 C10 1.364(6) . ?
N4 C9 1.350(6) . ?
N4 H4B 0.98(5) . ?
N4 H4A 0.89(6) . ?
C8 C7 1.324(7) . ?
C8 C9 1.434(6) . ?
C8 H8 0.9300 . ?
C4 C5 1.367(6) . ?
C4 H4 0.9300 . ?
O1 C2 1.214(5) . ?
C5 H5 0.9300 . ?
N1 C2 1.360(5) . ?
N1 H1 0.8600 . ?
C7 H7 0.9300 . ?
C2 C1 1.516(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C3 N2 C10 118.0(3) . . ?
C5 C6 C10 118.7(4) . . ?
C5 C6 C7 125.5(3) . . ?
C10 C6 C7 115.7(5) . . ?
N2 C3 C4 123.8(4) . . ?
N2 C3 N1 112.4(4) . . ?
C4 C3 N1 123.8(4) . . ?
C9 N3 C10 117.7(3) . . ?
C9 N4 H4B 114(3) . . ?
C9 N4 H4A 121(4) . . ?
H4B N4 H4A 120(4) . . ?
N2 C10 N3 115.0(3) . . ?
N2 C10 C6 121.2(5) . . ?
N3 C10 C6 123.8(5) . . ?
C7 C8 C9 119.2(5) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C2 N1 C3 127.5(4) . . ?
C2 N1 H1 116.3 . . ?
C3 N1 H1 116.3 . . ?
C8 C7 C6 121.5(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
O1 C2 N1 124.8(4) . . ?
O1 C2 C1 121.9(4) . . ?
N1 C2 C1 113.3(4) . . ?
N3 C9 N4 118.9(4) . . ?
N3 C9 C8 122.1(4) . . ?
N4 C9 C8 119.0(4) . . ?
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 . . ?

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 N2 C3 C4 1.6(7) . . . . ?
C10 N2 C3 N1 -178.5(4) . . . . ?
C3 N2 C10 N3 178.6(4) . . . . ?
C3 N2 C10 C6 -1.4(8) . . . . ?
C9 N3 C10 N2 179.1(4) . . . . ?
C9 N3 C10 C6 -0.9(8) . . . . ?
C5 C6 C10 N2 0.4(9) . . . . ?
C7 C6 C10 N2 179.0(5) . . . . ?
C5 C6 C10 N3 -179.6(5) . . . . ?
C7 C6 C10 N3 -1.0(10) . . . . ?
N2 C3 C4 C5 -0.7(8) . . . . ?
N1 C3 C4 C5 179.3(4) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C10 C6 C5 C4 0.5(9) . . . . ?
C7 C6 C5 C4 -178.0(5) . . . . ?
N2 C3 N1 C2 -176.5(4) . . . . ?
C4 C3 N1 C2 3.5(7) . . . . ?
C9 C8 C7 C6 -0.4(9) . . . . ?
C5 C6 C7 C8 -179.8(5) . . . . ?
C10 C6 C7 C8 1.6(9) . . . . ?
C3 N1 C2 O1 2.0(7) . . . . ?
C3 N1 C2 C1 179.5(4) . . . . ?
C10 N3 C9 N4 -179.4(5) . . . . ?
C10 N3 C9 C8 2.3(7) . . . . ?
C7 C8 C9 N3 -1.7(8) . . . . ?
C7 C8 C9 N4 -180.0(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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 N3 0.8600 2.1300 2.974(5) 166.00 6_555 yes
N4 H4A O1 0.90(6) 2.33(6) 3.180(5) 158(5) 8_453 yes
N4 H4B N2 0.97(5) 2.19(5) 3.130(6) 163(4) 6_554 yes
C4 H4 O1 0.9300 2.2600 2.854(5) 121.00 . yes
C8 H8 O1 0.9300 2.5700 3.364(6) 144.00 8_453 yes

_diffrn_measured_fraction_theta_max 0.834
_diffrn_reflns_theta_full        68.14
_diffrn_measured_fraction_theta_full 0.833
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.068
#===END