#data_New_Global_Publ_Block

data_global

_audit_creation_method            
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007. 
;

# 1. SUBMISSION DETAILS

_publ_contact_author_name
;
Guzei, Ilia A. 
;
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;

_publ_contact_author_phone    '608-263-4694'
_publ_contact_author_fax      '608-262-0381'
_publ_contact_author_email    iguzei@chem.wisc.edu

_publ_contact_letter
;
Please consider this CIF submission 
for publication in  
;

_publ_requested_journal      
;
;

_publ_requested_category  FA 
# FA 'Full article' 
# FI 'Full submission - inorganic (Acta C)' 
# FO 'Full submission - organic (Acta C)' 
# FM 'Full submission - metal-organic (Acta C)' 
# CI 'CIF-access paper - inorganic (Acta C)' 
# CO 'CIF-access paper - organic (Acta C)' 
# CM 'CIF-access paper - metal-organic (Acta C)' 

# 2. TITLE AND AUTHOR LIST

_publ_section_title  
;
;


loop_
_publ_author_name
_publ_author_address
'Guzei, Ilia A.'
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;
''
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;

_publ_section_synopsis
;
;

_publ_section_abstract
;
;

_publ_section_comment
;
;

_publ_section_references
;
Allen, F.H. (2002). <i>Acta Cryst.</i> <b>B58</b>, 380-388.

Bruker-AXS. (2007). APEX2 (Ver. 2.1-4), <i>SADABS</i>, <i>SAINTPLUS</i>,
<i>SHELXTL</i>. Bruker-AXS Inc., Madison, WI, USA.

Bruno, I. J., Cole, J. C.,  Edgington, P. R.,  Kessler, M., 
 Macrae, C. F.,  McCabe, P.,  Pearson, J,  
&  Taylor, R. (2002). <i>Acta Cryst.</i> <b>B58</b>, 389-397.

Cremer D. & Pople J.A.  (1975). <i>J. Am. Chem. Soc.</i> 
<b>97</b>, 1358-1367.

Frisch, M. J., Trucks, G. W.,
Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman,
J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant,
J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V.,
Mennucci, B. <i>et al.</i> (2004). 
Gaussian 03, Revision C.02,
Gaussian, Inc., Wallingford, CT, USA.

Guzei I.A. (2007).  In-house Crystallographic Programs: FCF_filter,INSerter,
modiCIFer.
Molecular Structure Laboratory, University of Wisconsin-Madison,
Madison, WI, USA.

Sheldrick, G.M. (2008). Acta Cryst. <b>A64</b>, 112-122.
;

_publ_section_acknowledgements
;
We thank the National Science Foundation for financial support. 

The manuscript was prepared with the beta test version 1.0.2. 
of program <i>publCIF</i> to be released by the IUCr and Ilia A. Guzei's
program <i>modiCIFer</i>.
;

_publ_section_figure_captions
;
Figure 1.  Molecular structure of (I).  The thermal ellipsoids are 
shown at 50% probability level.
;

_publ_section_exptl_prep
;
;


_publ_section_exptl_refinement
;
All H-atoms were placed in idealized locations and 
refined as riding with appropriate thermal displacement
coefficients U~iso~(H) = 1.2 or 1.5 times U~eq~(bearing atom). 
;

#3. data 
data_raines27 
  
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C8 H13 N O4' 
_chemical_formula_sum             'C8 H13 N O4' 
_chemical_formula_weight          187.19 
  
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    'P 21 21 21  '
_symmetry_space_group_name_Hall   'P 2ac 2ab   '
_symmetry_int_tables_number       19
  
_chemical_absolute_configuration  'syn'
# Options are 'rm', 'ad', 'rmad', 'syn', 'unk' or '.'
#                      
# rm   : absolute configuration established by the structure determination
#        of a compound containing a chiral reference molecule of known
#        absolute configuration.
# ad   : absolute configuration established by anomalous dispersion effects
#        in diffraction measurements on the crystal.
# rmad : absolute configuration established by the structure determination
#        of a compound containing a chiral reference molecule of known
#        absolute configuration and confirmed by anomalous dispersion
#        effects in diffraction measurements on the crystal.
# syn  : absolute configuration has not been established by anomalous
#        dispersion effects in diffraction measurements on the crystal.
#        The enantiomer has been assigned by reference to an unchanging
#        chiral centre in the synthetic procedure.
# unk  : absolute configuration is unknown, there being no firm chemical
#        evidence for its assignment to hand and it having not been 
#        established by anomalous dispersion effects in diffraction 
#        measurements on the crystal. An arbitrary choice of enantiomer
#        has been made.
# .    : inapplicable.
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    7.5448(2) 
_cell_length_b                    10.5798(4) 
_cell_length_c                    11.1164(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      887.34(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     2361 
_cell_measurement_theta_min       5.7733
_cell_measurement_theta_max       69.0136
  
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.44 
_exptl_crystal_size_mid           0.11 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.401 
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              400 
_exptl_absorpt_coefficient_mu     0.954 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min   0.6789 
_exptl_absorpt_correction_T_max   0.9106 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            Cu-K\a
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker SMART APEX2 area detector' 
_diffrn_measurement_method        '0.50\% \w and 0.5 \% \f scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             1645 
_diffrn_reflns_av_R_equivalents   0.0275 
_diffrn_reflns_av_sigmaI/netI     0.0286 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_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          5.77 
_diffrn_reflns_theta_max          70.07 
_reflns_number_total              984 
_reflns_number_gt                 916 
_reflns_threshold_expression      I>2\s(I) 
  
_computing_data_collection        'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_cell_refinement        'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction         'SAINT Ver. 7.24A'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material   'SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0524P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.0(4) 
_refine_ls_number_reflns          984 
_refine_ls_number_parameters      121 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0411 
_refine_ls_R_factor_gt            0.0381 
_refine_ls_wR_factor_ref          0.1022 
_refine_ls_wR_factor_gt           0.1003 
_refine_ls_goodness_of_fit_ref    1.107 
_refine_ls_restrained_S_all       1.107 
_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 0.4182(2) 0.34732(15) 0.57330(16) 0.0423(4) Uani 1 1 d . . . 
O2 O 0.6489(2) 0.48094(17) 0.58008(17) 0.0446(5) Uani 1 1 d . . . 
O3 O 0.6797(2) 0.27658(16) 0.81309(18) 0.0417(4) Uani 1 1 d . . . 
H3A H 0.7866 0.2987 0.8102 0.063 Uiso 1 1 calc R . . 
O4 O 0.0384(2) 0.31924(17) 0.82432(17) 0.0443(5) Uani 1 1 d . . . 
N1 N 0.3101(3) 0.40010(18) 0.79793(19) 0.0373(5) Uani 1 1 d . . . 
C1 C 0.4416(3) 0.4848(2) 0.7436(2) 0.0385(5) Uani 1 1 d . . . 
H1A H 0.3875 0.5701 0.7310 0.046 Uiso 1 1 calc R . . 
C2 C 0.5819(3) 0.4929(2) 0.8425(2) 0.0387(6) Uani 1 1 d . . . 
H2A H 0.5476 0.5548 0.9051 0.046 Uiso 1 1 calc R . . 
H2B H 0.6988 0.5169 0.8090 0.046 Uiso 1 1 calc R . . 
C3 C 0.5854(3) 0.3582(2) 0.8931(2) 0.0391(6) Uani 1 1 d . . . 
H3B H 0.6356 0.3556 0.9764 0.047 Uiso 1 1 calc R . . 
C4 C 0.3900(3) 0.3186(2) 0.8910(2) 0.0378(6) Uani 1 1 d . . . 
H4A H 0.3778 0.2282 0.8695 0.045 Uiso 1 1 calc R . . 
H4B H 0.3336 0.3331 0.9702 0.045 Uiso 1 1 calc R . . 
C5 C 0.1358(3) 0.3956(2) 0.7718(2) 0.0385(5) Uani 1 1 d . . . 
C6 C 0.0681(3) 0.4860(2) 0.6782(2) 0.0409(6) Uani 1 1 d . . . 
H6A H -0.0602 0.4752 0.6692 0.061 Uiso 1 1 calc R . . 
H6B H 0.1266 0.4687 0.6012 0.061 Uiso 1 1 calc R . . 
H6C H 0.0938 0.5729 0.7033 0.061 Uiso 1 1 calc R . . 
C7 C 0.5173(3) 0.4372(2) 0.6258(2) 0.0389(6) Uani 1 1 d . . . 
C8 C 0.4777(4) 0.3081(3) 0.4556(3) 0.0492(7) Uani 1 1 d . . . 
H8A H 0.3949 0.2457 0.4227 0.074 Uiso 1 1 calc R . . 
H8B H 0.5959 0.2703 0.4621 0.074 Uiso 1 1 calc R . . 
H8C H 0.4829 0.3817 0.4021 0.074 Uiso 1 1 calc R . . 
  
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0315(8) 0.0418(9) 0.0538(9) -0.0035(8) 0.0023(8) -0.0024(8) 
O2 0.0304(9) 0.0458(9) 0.0577(10) 0.0023(8) 0.0034(8) -0.0039(8) 
O3 0.0237(8) 0.0369(8) 0.0646(11) -0.0015(8) 0.0014(8) 0.0025(7) 
O4 0.0259(8) 0.0413(9) 0.0657(11) 0.0034(9) -0.0003(8) -0.0038(8) 
N1 0.0248(9) 0.0349(10) 0.0521(12) 0.0021(9) 0.0021(8) -0.0004(8) 
C1 0.0240(10) 0.0340(11) 0.0575(14) 0.0008(11) 0.0006(10) -0.0012(10) 
C2 0.0248(11) 0.0367(12) 0.0546(13) -0.0011(10) -0.0005(10) -0.0013(10) 
C3 0.0276(11) 0.0352(12) 0.0545(15) -0.0007(10) 0.0011(11) 0.0014(10) 
C4 0.0280(11) 0.0367(11) 0.0488(13) 0.0018(10) 0.0006(10) 0.0017(10) 
C5 0.0259(10) 0.0365(12) 0.0531(13) -0.0051(10) 0.0016(10) 0.0008(10) 
C6 0.0269(11) 0.0384(12) 0.0573(14) 0.0000(11) -0.0012(10) 0.0020(11) 
C7 0.0257(11) 0.0345(11) 0.0563(14) 0.0032(11) -0.0043(10) -0.0011(10) 
C8 0.0397(13) 0.0538(15) 0.0540(15) -0.0080(12) 0.0011(12) -0.0019(13) 
  
_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 C7 1.343(3) . yes
O1 C8 1.444(3) . yes
O2 C7 1.208(3) . yes
O3 C3 1.429(3) . yes
O3 H3A 0.8400 . ? 
O4 C5 1.238(3) . yes
N1 C5 1.348(3) . ? 
N1 C1 1.466(3) . ? 
N1 C4 1.476(3) . ? 
C1 C7 1.515(4) . ? 
C1 C2 1.528(3) . ? 
C1 H1A 1.0000 . ? 
C2 C3 1.533(3) . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C3 C4 1.533(3) . ? 
C3 H3B 1.0000 . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 C6 1.502(3) . ? 
C6 H6A 0.9800 . ? 
C6 H6B 0.9800 . ? 
C6 H6C 0.9800 . ? 
C8 H8A 0.9800 . ? 
C8 H8B 0.9800 . ? 
C8 H8C 0.9800 . ? 
  
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 
C7 O1 C8 115.1(2) . . yes
C3 O3 H3A 109.5 . . ? 
C5 N1 C1 126.4(2) . . ? 
C5 N1 C4 121.9(2) . . ? 
C1 N1 C4 111.68(18) . . ? 
N1 C1 C7 114.04(19) . . ? 
N1 C1 C2 101.95(19) . . ? 
C7 C1 C2 112.24(18) . . ? 
N1 C1 H1A 109.4 . . ? 
C7 C1 H1A 109.4 . . ? 
C2 C1 H1A 109.4 . . ? 
C1 C2 C3 102.93(18) . . ? 
C1 C2 H2A 111.2 . . ? 
C3 C2 H2A 111.2 . . ? 
C1 C2 H2B 111.2 . . ? 
C3 C2 H2B 111.2 . . ? 
H2A C2 H2B 109.1 . . ? 
O3 C3 C4 107.71(19) . . ? 
O3 C3 C2 109.9(2) . . ? 
C4 C3 C2 103.4(2) . . ? 
O3 C3 H3B 111.8 . . ? 
C4 C3 H3B 111.8 . . ? 
C2 C3 H3B 111.8 . . ? 
N1 C4 C3 104.1(2) . . ? 
N1 C4 H4A 110.9 . . ? 
C3 C4 H4A 110.9 . . ? 
N1 C4 H4B 110.9 . . ? 
C3 C4 H4B 110.9 . . ? 
H4A C4 H4B 108.9 . . ? 
O4 C5 N1 120.0(2) . . ? 
O4 C5 C6 122.7(2) . . ? 
N1 C5 C6 117.3(2) . . ? 
C5 C6 H6A 109.5 . . ? 
C5 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
C5 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
O2 C7 O1 123.1(2) . . ? 
O2 C7 C1 123.1(2) . . ? 
O1 C7 C1 113.6(2) . . ? 
O1 C8 H8A 109.5 . . ? 
O1 C8 H8B 109.5 . . ? 
H8A C8 H8B 109.5 . . ? 
O1 C8 H8C 109.5 . . ? 
H8A C8 H8C 109.5 . . ? 
H8B C8 H8C 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 
C5 N1 C1 C7 -84.4(3) . . . . ? 
C4 N1 C1 C7 97.2(2) . . . . ? 
C5 N1 C1 C2 154.4(2) . . . . ? 
C4 N1 C1 C2 -24.0(2) . . . . ? 
N1 C1 C2 C3 37.7(2) . . . . ? 
C7 C1 C2 C3 -84.7(2) . . . . ? 
C1 C2 C3 O3 76.6(2) . . . . ? 
C1 C2 C3 C4 -38.2(2) . . . . ? 
C5 N1 C4 C3 -178.1(2) . . . . ? 
C1 N1 C4 C3 0.3(3) . . . . ? 
O3 C3 C4 N1 -92.8(2) . . . . ? 
C2 C3 C4 N1 23.6(2) . . . . ? 
C1 N1 C5 O4 180.0(2) . . . . ? 
C4 N1 C5 O4 -1.9(4) . . . . ? 
C1 N1 C5 C6 -0.1(4) . . . . ? 
C4 N1 C5 C6 178.0(2) . . . . ? 
C8 O1 C7 O2 -1.4(3) . . . . ? 
C8 O1 C7 C1 174.5(2) . . . . ? 
N1 C1 C7 O2 -165.6(2) . . . . ? 
C2 C1 C7 O2 -50.3(3) . . . . ? 
N1 C1 C7 O1 18.5(3) . . . . ? 
C2 C1 C7 O1 133.8(2) . . . . ? 
  
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 
O3 H3A O4  0.84 1.92 2.746(2) 168.2 1_655 
  
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              70.07 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.146 
_refine_diff_density_min   -0.224 
_refine_diff_density_rms    0.043 
 
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.