Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Lucia Maini'
_publ_contact_author_address     
;
Dipartimento di Chimica
Universita delgi studi di Bologna
via Selmi 2
Bologna
40126
ITALY
;

_publ_contact_author_email       LUCIAMAINI@UNIBO.IT

_publ_section_title              
;
Gas-Solid Reactions between the Different
Polymorphic Modifications of Barbituric Acid and Amines
;
loop_
_publ_author_name
'Lucia Maini'
'Dario Braga'
M.Cadoni
F.Grepioni
'Katia Rubini'

# Attachment '1b.cif'

data_piccola
_database_code_depnum_ccdc_archive 'CCDC 294126'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H9 N3 O3'
_chemical_formula_weight         159.15

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.544(3)
_cell_length_b                   9.588(3)
_cell_length_c                   9.915(3)
_cell_angle_alpha                86.554(5)
_cell_angle_beta                 68.376(5)
_cell_angle_gamma                63.175(5)
_cell_volume                     746.5(4)
_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            'light pink'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   sadabs
_exptl_absorpt_correction_T_min  0.7572
_exptl_absorpt_correction_T_max  1.000
_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  'area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8594
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.55
_reflns_number_total             3449
_reflns_number_gt                1625
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker apex2'
_computing_cell_refinement       Apex2
_computing_data_reduction        saint
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    schakal
_computing_publication_material  wingX

_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^)+(0.1550P)^2^+1.7662P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3449
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0917
_refine_ls_wR_factor_ref         0.3479
_refine_ls_wR_factor_gt          0.3044
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.4756(7) 0.2986(6) 0.9863(5) 0.0350(12) Uani 1 1 d . . .
C2 C 0.4789(7) 0.3472(6) 0.7409(6) 0.0341(12) Uani 1 1 d . . .
C3 C 0.6694(7) 0.0920(6) 0.7839(6) 0.0348(12) Uani 1 1 d . . .
C4 C 0.5999(7) 0.1452(6) 0.9321(6) 0.0371(13) Uani 1 1 d . . .
H4 H 0.6374 0.0766 0.9959 0.045 Uiso 1 1 calc R . .
N1 N 0.4172(6) 0.3933(5) 0.8874(5) 0.0377(11) Uani 1 1 d . . .
N2 N 0.6024(6) 0.1972(5) 0.6945(5) 0.0380(11) Uani 1 1 d . . .
O1 O 0.4083(5) 0.3640(5) 1.1157(4) 0.0478(11) Uani 1 1 d . . .
O2 O 0.4244(5) 0.4364(4) 0.6580(4) 0.0447(11) Uani 1 1 d . . .
O3 O 0.7882(5) -0.0428(4) 0.7218(4) 0.0455(11) Uani 1 1 d . . .
H100 H 0.328(9) 0.497(8) 0.919(7) 0.06(2) Uiso 1 1 d . . .
H200 H 0.657(7) 0.157(7) 0.595(7) 0.042(16) Uiso 1 1 d . . .
C5 C 0.0835(7) 0.7620(6) 0.1238(6) 0.0366(13) Uani 1 1 d . . .
C6 C 0.0887(7) 0.7159(6) 0.3668(6) 0.0347(12) Uani 1 1 d . . .
C7 C -0.1167(7) 0.9653(6) 0.3282(6) 0.0358(13) Uani 1 1 d . . .
C8 C -0.0544(7) 0.9117(7) 0.1820(6) 0.0438(15) Uani 1 1 d . . .
H8 H -0.1042 0.9755 0.1214 0.053 Uiso 1 1 calc R . .
N3 N 0.1480(6) 0.6714(5) 0.2213(5) 0.0357(11) Uani 1 1 d . . .
N4 N -0.0429(6) 0.8642(5) 0.4154(5) 0.0375(11) Uani 1 1 d . . .
O5 O 0.1531(5) 0.7018(5) -0.0067(4) 0.0522(12) Uani 1 1 d . . .
O6 O 0.1495(5) 0.6300(4) 0.4482(4) 0.0463(11) Uani 1 1 d . . .
O7 O -0.2368(5) 1.1011(5) 0.3912(4) 0.0471(11) Uani 1 1 d . . .
H300 H 0.241(7) 0.576(7) 0.178(6) 0.032(14) Uiso 1 1 d . . .
H400 H -0.100(8) 0.907(8) 0.508(8) 0.055(19) Uiso 1 1 d . . .
H500 H 0.476(8) 0.320(7) 0.268(7) 0.050(17) Uiso 1 1 d . . .
H501 H 0.602(11) 0.225(10) 0.343(9) 0.10(3) Uiso 1 1 d . . .
H502 H 0.428(8) 0.394(8) 0.420(7) 0.05(2) Uiso 1 1 d . . .
H600 H 1.044(10) 0.192(9) 0.217(8) 0.08(2) Uiso 1 1 d . . .
H601 H 0.904(10) 0.286(9) 0.162(9) 0.08(2) Uiso 1 1 d . . .
H602 H 0.873(8) 0.310(8) 0.321(8) 0.05(2) Uiso 1 1 d . . .
C9 C 0.3525(9) 0.2419(9) 0.4423(8) 0.0629(19) Uani 1 1 d . . .
H9A H 0.3656 0.2101 0.5324 0.094 Uiso 1 1 calc R . .
H9B H 0.3801 0.1519 0.3811 0.094 Uiso 1 1 calc R . .
H9C H 0.2371 0.3193 0.4627 0.094 Uiso 1 1 calc R . .
N5 N 0.4651(7) 0.3087(6) 0.3680(6) 0.0404(12) Uani 1 1 d . . .
C10 C 1.0092(10) 0.4071(9) 0.1997(9) 0.067(2) Uani 1 1 d . . .
H10A H 0.9160 0.5071 0.2037 0.100 Uiso 1 1 calc R . .
H10B H 1.0961 0.3770 0.1030 0.100 Uiso 1 1 calc R . .
H10C H 1.0548 0.4150 0.2688 0.100 Uiso 1 1 calc R . .
N6 N 0.9500(7) 0.2893(6) 0.2351(6) 0.0405(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.039(3) 0.037(3) 0.024(3) 0.005(2) -0.016(2) -0.011(2)
C2 0.035(3) 0.030(3) 0.030(3) 0.002(2) -0.017(2) -0.006(2)
C3 0.031(3) 0.032(3) 0.033(3) 0.003(2) -0.015(2) -0.006(2)
C4 0.037(3) 0.032(3) 0.030(3) 0.001(2) -0.017(2) -0.002(2)
N1 0.037(3) 0.032(2) 0.027(2) 0.0012(19) -0.015(2) 0.000(2)
N2 0.034(2) 0.037(3) 0.028(2) -0.002(2) -0.015(2) -0.001(2)
O1 0.048(2) 0.047(2) 0.024(2) -0.0038(17) -0.0169(18) 0.0010(19)
O2 0.048(2) 0.039(2) 0.033(2) 0.0025(17) -0.0240(18) -0.0012(18)
O3 0.048(2) 0.032(2) 0.036(2) -0.0015(17) -0.0188(18) 0.0003(18)
C5 0.039(3) 0.034(3) 0.030(3) -0.003(2) -0.019(2) -0.006(2)
C6 0.036(3) 0.032(3) 0.029(3) 0.003(2) -0.014(2) -0.009(2)
C7 0.031(3) 0.033(3) 0.030(3) -0.003(2) -0.010(2) -0.004(2)
C8 0.036(3) 0.046(3) 0.037(3) 0.004(3) -0.024(3) -0.001(3)
N3 0.036(3) 0.033(2) 0.027(2) 0.0019(19) -0.017(2) -0.004(2)
N4 0.037(3) 0.033(2) 0.029(2) 0.000(2) -0.014(2) -0.004(2)
O5 0.055(3) 0.045(2) 0.033(2) -0.0087(18) -0.0242(19) 0.0040(19)
O6 0.050(2) 0.037(2) 0.032(2) 0.0028(17) -0.0198(19) -0.0004(18)
O7 0.042(2) 0.039(2) 0.032(2) -0.0007(17) -0.0156(18) 0.0064(18)
C9 0.071(5) 0.061(4) 0.065(5) 0.014(4) -0.033(4) -0.033(4)
N5 0.043(3) 0.036(3) 0.034(3) 0.000(2) -0.021(2) -0.006(2)
C10 0.070(5) 0.075(5) 0.076(5) 0.025(4) -0.036(4) -0.046(4)
N6 0.037(3) 0.039(3) 0.036(3) 0.004(2) -0.018(2) -0.008(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
C1 O1 1.256(6) . ?
C1 C4 1.382(7) . ?
C1 N1 1.391(6) . ?
C2 O2 1.227(6) . ?
C2 N2 1.349(6) . ?
C2 N1 1.366(6) . ?
C3 O3 1.262(6) . ?
C3 C4 1.388(7) . ?
C3 N2 1.393(7) . ?
C4 H4 0.9300 . ?
N1 H100 0.94(7) . ?
N2 H200 0.94(6) . ?
C5 O5 1.248(6) . ?
C5 N3 1.386(6) . ?
C5 C8 1.400(7) . ?
C6 O6 1.224(6) . ?
C6 N3 1.356(7) . ?
C6 N4 1.363(7) . ?
C7 O7 1.273(6) . ?
C7 C8 1.377(7) . ?
C7 N4 1.384(7) . ?
C8 H8 0.9300 . ?
N3 H300 0.92(6) . ?
N4 H400 0.89(7) . ?
C9 N5 1.446(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N5 H500 0.97(7) . ?
N5 H501 1.12(9) . ?
N5 H502 0.85(7) . ?
C10 N6 1.449(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N6 H600 0.92(8) . ?
N6 H601 0.99(8) . ?
N6 H602 0.86(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
O1 C1 C4 127.5(5) . . ?
O1 C1 N1 115.4(5) . . ?
C4 C1 N1 117.1(5) . . ?
O2 C2 N2 122.7(5) . . ?
O2 C2 N1 122.0(5) . . ?
N2 C2 N1 115.3(5) . . ?
O3 C3 C4 126.3(5) . . ?
O3 C3 N2 116.6(5) . . ?
C4 C3 N2 117.1(5) . . ?
C1 C4 C3 120.9(5) . . ?
C1 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C2 N1 C1 124.6(4) . . ?
C2 N1 H100 114(4) . . ?
C1 N1 H100 121(4) . . ?
C2 N2 C3 124.8(5) . . ?
C2 N2 H200 121(4) . . ?
C3 N2 H200 114(4) . . ?
O5 C5 N3 117.0(5) . . ?
O5 C5 C8 126.4(5) . . ?
N3 C5 C8 116.6(5) . . ?
O6 C6 N3 122.7(5) . . ?
O6 C6 N4 122.5(5) . . ?
N3 C6 N4 114.8(5) . . ?
O7 C7 C8 125.8(5) . . ?
O7 C7 N4 116.5(5) . . ?
C8 C7 N4 117.8(5) . . ?
C7 C8 C5 120.5(5) . . ?
C7 C8 H8 119.7 . . ?
C5 C8 H8 119.7 . . ?
C6 N3 C5 125.5(5) . . ?
C6 N3 H300 121(3) . . ?
C5 N3 H300 114(3) . . ?
C6 N4 C7 124.7(5) . . ?
C6 N4 H400 125(4) . . ?
C7 N4 H400 110(4) . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 N5 H500 112(4) . . ?
C9 N5 H501 113(4) . . ?
H500 N5 H501 97(5) . . ?
C9 N5 H502 106(4) . . ?
H500 N5 H502 114(6) . . ?
H501 N5 H502 114(6) . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C10 N6 H600 108(5) . . ?
C10 N6 H601 107(4) . . ?
H600 N6 H601 105(6) . . ?
C10 N6 H602 113(4) . . ?
H600 N6 H602 114(6) . . ?
H601 N6 H602 109(6) . . ?

_diffrn_measured_fraction_theta_max 0.909
_diffrn_reflns_theta_full        28.55
_diffrn_measured_fraction_theta_full 0.909
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.111

# Attachment '1c.CIF'

data_fab_1c
_database_code_depnum_ccdc_archive 'CCDC 294127'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H11 N3 O3'
_chemical_formula_weight         173.18

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   Pnma

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

_cell_length_a                   14.023(9)
_cell_length_b                   12.02(2)
_cell_length_c                   9.949(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1677(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      8.00
_cell_measurement_theta_max      15.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  1.00
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2929
_diffrn_reflns_av_R_equivalents  0.1444
_diffrn_reflns_av_sigmaI/netI    0.1114
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.07
_reflns_number_total             1551
_reflns_number_gt                933
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0851P)^2^+0.0024P] 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     SHELXL
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
C1 C 1.0643(3) 0.7500 0.2296(3) 0.0438(9) Uani 1 2 d S . .
C2 C 0.9295(2) 0.85070(16) 0.1343(2) 0.0426(6) Uani 1 1 d . . .
C3 C 0.8855(3) 0.7500 0.1040(3) 0.0465(9) Uani 1 2 d S . .
H3 H 0.8257 0.7500 0.0636 0.072(13) Uiso 1 2 d SR . .
N1 N 1.01739(16) 0.84600(15) 0.19608(18) 0.0465(6) Uani 1 1 d . . .
H1 H 1.0447 0.9080 0.2153 0.053(8) Uiso 1 1 d R . .
O1 O 1.1428(2) 0.7500 0.2853(3) 0.0579(8) Uani 1 2 d S . .
O2 O 0.89655(14) 0.94781(13) 0.11067(17) 0.0529(6) Uani 1 1 d . . .
C4 C 1.0582(3) 0.7500 -0.1547(3) 0.0456(9) Uani 1 2 d S . .
C5 C 0.9226(2) 0.85064(16) -0.2463(2) 0.0457(7) Uani 1 1 d . . .
C6 C 0.8787(3) 0.7500 -0.2768(3) 0.0483(10) Uani 1 2 d S . .
H6 H 0.8192 0.7500 -0.3181 0.060(12) Uiso 1 2 d SR . .
N2 N 1.01067(16) 0.84602(14) -0.18492(18) 0.0456(6) Uani 1 1 d . . .
H2 H 1.0374 0.9080 -0.1638 0.051(7) Uiso 1 1 d R . .
O3 O 1.1383(2) 0.7500 -0.1061(3) 0.0647(8) Uani 1 2 d S . .
O4 O 0.88910(14) 0.94732(13) -0.27062(18) 0.0599(6) Uani 1 1 d . . .
N3 N 0.71938(18) 1.00058(15) 0.00591(19) 0.0492(6) Uani 1 1 d . . .
H3B H 0.7780 0.9765 0.0286 0.063(8) Uiso 1 1 d R . .
H3C H 0.6894 1.0217 0.0817 0.063(9) Uiso 1 1 d R . .
C7 C 0.7282(3) 1.0974(2) -0.0846(3) 0.0644(9) Uani 1 1 d . . .
H7A H 0.7636 1.1552 -0.0404 0.124(14) Uiso 1 1 d R . .
H7B H 0.6658 1.1245 -0.1073 0.087(12) Uiso 1 1 d R . .
H7C H 0.7610 1.0754 -0.1650 0.085(11) Uiso 1 1 d R . .
C8 C 0.6662(3) 0.9093(2) -0.0564(3) 0.0717(10) Uani 1 1 d . . .
H8A H 0.6613 0.8486 0.0059 0.151(18) Uiso 1 1 d R . .
H8B H 0.6991 0.8849 -0.1358 0.090(11) Uiso 1 1 d R . .
H8C H 0.6035 0.9345 -0.0802 0.084(12) 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
C1 0.070(3) 0.0078(15) 0.054(2) 0.000 -0.0013(18) 0.000
C2 0.0699(16) 0.0054(11) 0.0526(14) 0.0009(8) -0.0014(12) 0.0029(11)
C3 0.071(3) 0.0062(17) 0.062(2) 0.000 -0.0071(17) 0.000
N1 0.0727(15) 0.0031(10) 0.0639(12) -0.0005(7) -0.0060(11) -0.0021(9)
O1 0.080(2) 0.0141(13) 0.0792(18) 0.000 -0.0160(15) 0.000
O2 0.0794(13) 0.0037(9) 0.0756(12) 0.0012(7) -0.0095(9) 0.0044(8)
C4 0.070(3) 0.0099(15) 0.057(2) 0.000 -0.0020(19) 0.000
C5 0.0797(18) 0.0065(11) 0.0509(13) 0.0018(9) -0.0074(13) 0.0042(11)
C6 0.075(3) 0.0064(16) 0.063(2) 0.000 -0.0136(19) 0.000
N2 0.0747(15) 0.0027(10) 0.0593(12) 0.0014(7) -0.0058(11) -0.0043(9)
O3 0.079(2) 0.0198(15) 0.096(2) 0.000 -0.0180(16) 0.000
O4 0.0995(15) 0.0022(8) 0.0780(12) 0.0022(7) -0.0231(10) 0.0048(8)
N3 0.0793(16) 0.0171(10) 0.0513(11) -0.0014(8) -0.0009(11) 0.0066(10)
C7 0.109(3) 0.0183(14) 0.0662(17) 0.0047(11) -0.0047(17) -0.0113(16)
C8 0.112(3) 0.0192(14) 0.084(2) -0.0009(13) -0.005(2) -0.0134(17)

_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
C1 O1 1.232(5) . ?
C1 N1 1.369(3) 8_575 ?
C1 N1 1.369(3) . ?
C2 O2 1.277(3) . ?
C2 N1 1.379(3) . ?
C2 C3 1.391(3) . ?
C3 C2 1.391(3) 8_575 ?
C3 H3 0.9299 . ?
N1 H1 0.8599 . ?
C4 O3 1.224(5) . ?
C4 N2 1.366(3) 8_575 ?
C4 N2 1.366(3) . ?
C5 O4 1.277(3) . ?
C5 N2 1.379(4) . ?
C5 C6 1.391(3) . ?
C6 C5 1.391(3) 8_575 ?
C6 H6 0.9301 . ?
N2 H2 0.8604 . ?
N3 C8 1.464(4) . ?
N3 C7 1.477(3) . ?
N3 H3B 0.9007 . ?
N3 H3C 0.8996 . ?
C7 H7A 0.9604 . ?
C7 H7B 0.9599 . ?
C7 H7C 0.9599 . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9603 . ?
C8 H8C 0.9603 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 122.59(18) . 8_575 ?
O1 C1 N1 122.59(18) . . ?
N1 C1 N1 114.8(4) 8_575 . ?
O2 C2 N1 116.3(2) . . ?
O2 C2 C3 126.5(3) . . ?
N1 C2 C3 117.2(2) . . ?
C2 C3 C2 120.9(4) 8_575 . ?
C2 C3 H3 119.5 8_575 . ?
C2 C3 H3 119.5 . . ?
C1 N1 C2 124.9(2) . . ?
C1 N1 H1 117.5 . . ?
C2 N1 H1 117.5 . . ?
O3 C4 N2 122.33(17) . 8_575 ?
O3 C4 N2 122.33(17) . . ?
N2 C4 N2 115.3(3) 8_575 . ?
O4 C5 N2 116.7(2) . . ?
O4 C5 C6 126.0(3) . . ?
N2 C5 C6 117.3(2) . . ?
C5 C6 C5 120.8(4) . 8_575 ?
C5 C6 H6 119.6 . . ?
C5 C6 H6 119.6 8_575 . ?
C4 N2 C5 124.6(2) . . ?
C4 N2 H2 117.8 . . ?
C5 N2 H2 117.6 . . ?
C8 N3 C7 112.0(2) . . ?
C8 N3 H3B 109.3 . . ?
C7 N3 H3B 109.3 . . ?
C8 N3 H3C 109.1 . . ?
C7 N3 H3C 109.1 . . ?
H3B N3 H3C 107.9 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.3 . . ?
H7A C7 H7C 109.4 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.4 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.4 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.071


# Attachment '1a.CIF'

data_fab_1a
_database_code_depnum_ccdc_archive 'CCDC 294128'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H7 N3 O3'
_chemical_formula_weight         145.13

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.713(3)
_cell_length_b                   3.858(2)
_cell_length_c                   14.347(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.15(3)
_cell_angle_gamma                90.00
_cell_volume                     589.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8
_cell_measurement_theta_max      10

_exptl_crystal_description       prism
_exptl_crystal_colour            'light pink'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   Psi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  1.00
_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  scintillation
_diffrn_measurement_method       'omega-two theta'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1202
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1039
_reflns_number_gt                704
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Enraf Nonius software'
_computing_cell_refinement       'Enraf Nonius software'
_computing_data_reduction        wingx
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    schakal
_computing_publication_material  wingX

_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^)+(0.0729P)^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     SHELXL
_refine_ls_extinction_coef       0.020(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1039
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.3149(2) 0.4978(6) 0.38776(17) 0.0210(5) Uani 1 1 d . . .
O1 O 0.38459(15) 0.5850(5) 0.32584(12) 0.0295(5) Uani 1 1 d . . .
N1 N 0.20785(18) 0.3054(5) 0.35743(14) 0.0221(5) Uani 1 1 d . . .
H1 H 0.196(3) 0.243(8) 0.298(2) 0.037(8) Uiso 1 1 d . . .
C2 C 0.1232(2) 0.1911(6) 0.41417(16) 0.0195(5) Uani 1 1 d . . .
O2 O 0.03001(15) 0.0173(4) 0.38270(11) 0.0285(5) Uani 1 1 d . . .
N2 N 0.14404(18) 0.2807(5) 0.50533(14) 0.0216(5) Uani 1 1 d . . .
H2 H 0.091(2) 0.204(7) 0.5439(18) 0.020(6) Uiso 1 1 d . . .
C3 C 0.2479(2) 0.4690(6) 0.54401(16) 0.0220(6) Uani 1 1 d . . .
O3 O 0.25455(16) 0.5248(5) 0.63098(11) 0.0312(5) Uani 1 1 d . . .
C4 C 0.3333(2) 0.5755(7) 0.48312(17) 0.0246(6) Uani 1 1 d . . .
H4 H 0.409(3) 0.723(8) 0.5087(19) 0.043(8) Uiso 1 1 d . . .
N3 N 0.4287(2) 0.9402(7) 0.73152(17) 0.0274(6) Uani 1 1 d . . .
H5 H 0.386(3) 1.025(8) 0.777(2) 0.040(9) Uiso 1 1 d . . .
H6 H 0.471(3) 1.097(10) 0.699(2) 0.048(9) Uiso 1 1 d . . .
H7 H 0.485(4) 0.780(12) 0.756(3) 0.068(12) Uiso 1 1 d . . .
H8 H 0.368(3) 0.823(9) 0.689(2) 0.054(10) 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
C1 0.0199(12) 0.0221(12) 0.0211(12) 0.0041(11) 0.0034(9) 0.0034(10)
O1 0.0273(9) 0.0377(11) 0.0246(10) 0.0023(8) 0.0075(7) -0.0061(8)
N1 0.0221(10) 0.0278(11) 0.0161(10) -0.0020(9) 0.0008(8) -0.0042(9)
C2 0.0196(12) 0.0213(12) 0.0177(11) -0.0015(10) 0.0021(9) 0.0009(10)
O2 0.0264(9) 0.0381(11) 0.0207(9) -0.0042(8) 0.0008(7) -0.0120(8)
N2 0.0205(10) 0.0279(11) 0.0167(10) -0.0010(9) 0.0037(8) -0.0050(9)
C3 0.0232(12) 0.0246(12) 0.0173(12) -0.0007(10) -0.0022(9) 0.0010(11)
O3 0.0323(10) 0.0452(11) 0.0162(9) -0.0050(8) 0.0026(7) -0.0113(9)
C4 0.0209(12) 0.0281(13) 0.0244(13) -0.0001(11) 0.0004(10) -0.0022(11)
N3 0.0267(12) 0.0287(12) 0.0268(13) -0.0027(11) 0.0025(11) -0.0013(11)

_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
C1 O1 1.266(3) . ?
C1 C4 1.394(3) . ?
C1 N1 1.396(3) . ?
N1 C2 1.356(3) . ?
N1 H1 0.89(3) . ?
C2 O2 1.246(3) . ?
C2 N2 1.348(3) . ?
N2 C3 1.393(3) . ?
N2 H2 0.89(3) . ?
C3 O3 1.261(3) . ?
C3 C4 1.394(3) . ?
C4 H4 1.03(3) . ?
N3 H5 0.90(3) . ?
N3 H6 0.91(4) . ?
N3 H7 0.91(5) . ?
N3 H8 0.96(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 126.9(2) . . ?
O1 C1 N1 116.7(2) . . ?
C4 C1 N1 116.5(2) . . ?
C2 N1 C1 124.5(2) . . ?
C2 N1 H1 117.4(18) . . ?
C1 N1 H1 118.1(18) . . ?
O2 C2 N2 122.2(2) . . ?
O2 C2 N1 121.3(2) . . ?
N2 C2 N1 116.6(2) . . ?
C2 N2 C3 124.2(2) . . ?
C2 N2 H2 118.0(16) . . ?
C3 N2 H2 117.7(16) . . ?
O3 C3 C4 126.8(2) . . ?
O3 C3 N2 116.2(2) . . ?
C4 C3 N2 117.0(2) . . ?
C3 C4 C1 121.2(2) . . ?
C3 C4 H4 119.1(15) . . ?
C1 C4 H4 119.6(15) . . ?
H5 N3 H6 117(3) . . ?
H5 N3 H7 109(3) . . ?
H6 N3 H7 108(3) . . ?
H5 N3 H8 106(3) . . ?
H6 N3 H8 109(3) . . ?
H7 N3 H8 108(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.056

