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

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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_fun8m
_database_code_depnum_ccdc_archive 'CCDC 612395'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H11 N3 O3'
_chemical_formula_weight         149.16

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   12.1682(19)
_cell_length_b                   5.0450(8)
_cell_length_c                   12.494(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.948(2)
_cell_angle_gamma                90.00
_cell_volume                     725.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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            3368
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1263
_reflns_number_gt                1188
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0760P)^2^+0.0903P] 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       0.122(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1263
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.74351(8) 0.10421(19) 0.37531(8) 0.0502(3) Uani 1 1 d . . .
O2 O 0.90164(8) -0.0292(2) 0.34801(8) 0.0484(3) Uani 1 1 d . . .
O1W O 0.51489(10) 0.1396(2) 0.30998(12) 0.0648(4) Uani 1 1 d . . .
H1W1 H 0.588(2) 0.123(4) 0.3427(18) 0.079(6) Uiso 1 1 d . . .
H2W1 H 0.504(2) 0.292(5) 0.273(2) 0.095(7) Uiso 1 1 d . . .
N1 N 0.77413(9) -0.2159(2) 0.56429(8) 0.0376(3) Uani 1 1 d . . .
N2 N 0.88060(10) 0.1305(2) 0.67144(10) 0.0439(3) Uani 1 1 d . . .
H1N2 H 0.8875(14) 0.255(4) 0.7223(14) 0.051(4) Uiso 1 1 d . . .
H2N2 H 0.9398(15) 0.102(3) 0.6485(13) 0.052(4) Uiso 1 1 d . . .
N3 N 0.71087(10) 0.0275(2) 0.69202(10) 0.0435(3) Uani 1 1 d . . .
H2N3 H 0.6434(17) -0.053(3) 0.6725(14) 0.054(4) Uiso 1 1 d . . .
H1N3 H 0.7247(14) 0.147(3) 0.7463(14) 0.050(4) Uiso 1 1 d . . .
C1 C 0.82950(9) -0.0383(2) 0.39813(9) 0.0350(3) Uani 1 1 d . . .
C2 C 0.84968(11) -0.2425(2) 0.49583(10) 0.0378(4) Uani 1 1 d . . .
H2A H 0.8353(12) -0.418(3) 0.4586(12) 0.043(4) Uiso 1 1 d . . .
H2B H 0.9262(13) -0.230(3) 0.5435(12) 0.043(3) Uiso 1 1 d . . .
C3 C 0.78893(10) -0.0209(2) 0.64229(9) 0.0351(3) Uani 1 1 d . . .
C4 C 0.66908(14) -0.3667(3) 0.52830(15) 0.0524(4) Uani 1 1 d . . .
H4C H 0.6083(17) -0.261(4) 0.4859(15) 0.070(5) Uiso 1 1 d . . .
H4B H 0.6757(19) -0.507(5) 0.4805(19) 0.092(7) Uiso 1 1 d . . .
H4A H 0.6546(18) -0.438(4) 0.5966(18) 0.079(5) 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
O1 0.0377(5) 0.0581(6) 0.0604(6) 0.0176(4) 0.0236(4) 0.0126(4)
O2 0.0353(5) 0.0659(6) 0.0500(6) 0.0070(4) 0.0224(4) 0.0041(4)
O1W 0.0350(6) 0.0644(8) 0.0948(9) 0.0069(6) 0.0206(6) -0.0063(5)
N1 0.0382(6) 0.0393(6) 0.0389(5) -0.0008(4) 0.0174(4) -0.0024(4)
N2 0.0338(6) 0.0512(7) 0.0511(7) -0.0115(5) 0.0197(5) -0.0037(5)
N3 0.0353(6) 0.0514(7) 0.0493(6) -0.0093(5) 0.0214(5) -0.0047(5)
C1 0.0288(6) 0.0410(6) 0.0362(6) -0.0026(5) 0.0121(5) -0.0019(5)
C2 0.0365(7) 0.0400(7) 0.0392(6) -0.0014(5) 0.0154(5) 0.0052(5)
C3 0.0329(6) 0.0384(6) 0.0357(6) 0.0042(4) 0.0136(5) 0.0025(4)
C4 0.0504(8) 0.0497(8) 0.0620(9) -0.0094(7) 0.0250(7) -0.0124(6)

_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 1.2246(15) . ?
O2 C1 1.2337(14) . ?
N1 C3 1.3552(16) . ?
N1 C4 1.4288(17) . ?
N1 C2 1.4509(15) . ?
N2 C3 1.3023(17) . ?
N3 C3 1.3158(15) . ?
C1 C2 1.5547(17) . ?

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 N1 C4 120.61(11) . . ?
C3 N1 C2 121.97(10) . . ?
C4 N1 C2 116.01(11) . . ?
O1 C1 O2 123.71(11) . . ?
O1 C1 C2 118.50(10) . . ?
O2 C1 C2 117.80(10) . . ?
N1 C2 C1 115.64(9) . . ?
N2 C3 N3 116.31(12) . . ?
N2 C3 N1 121.91(11) . . ?
N3 C3 N1 121.78(11) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044



