##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section B. It has been peer reviewed under the auspices  #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary may be obtained from        #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
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data_0.0
_audit_creation_method     CRYSTALS_ver_12-03-99
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_address
;
Chemical Crystallography Laboratory
9 Parks Road
OXFORD OX1 3PD
;
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '0131650 4804'
_publ_section_title
;
 ?                                     # Title of paper
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ?                                                #footnote for author 1
;
;
 ?                                                # Address for author 1
;
    'Else, S. O.'
;
 ?                                                # footnote 2
;
;
 ?                                                # Address 2
;
_chemical_name_systematic
;
?
;
_chemical_formula_moiety     ' C5 H10 N2 O3 '
_chemical_formula_sum     ' C5 H10 N2 O3 '
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     16.023(3)
_cell_length_b     7.7678(18)
_cell_length_c     5.1004(13)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     634.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     348
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     23.78
_cell_measurement_temperature     293
_exptl_crystal_description     ' block '
_exptl_crystal_colour     ' colourless '
_exptl_crystal_density_diffrn     1.529
_exptl_crystal_F_000     312.000
_exptl_absorpt_coefficient_mu     0.126
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SORTAV (Blessing)
;
_exptl_absorpt_correction_T_min     0.407
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     337
_diffrn_reflns_av_R_equivalents     0.1842
_diffrn_reflns_theta_min     2.542
_diffrn_reflns_theta_max     23.215
_diffrn_reflns_theta_full     17.586
_diffrn_measured_fraction_theta_max     0.572
_diffrn_measured_fraction_theta_full     0.668
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -3
_diffrn_reflns_limit_l_max     3
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0.00
_reflns_number_total     326
_reflns_number_gt     202
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1548
_refine_ls_R_factor_gt     0.1045
_refine_ls_wR_factor_all     0.2631
_refine_ls_wR_factor_gt     0.2355
_refine_ls_wR_factor_ref     0.2631
_refine_ls_goodness_of_fit_ref     1.0463
_refine_ls_number_reflns     297
_refine_ls_number_parameters     41
_refine_ls_hydrogen_treatment     fixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = SHELXL 97 (Sheldrick, 1997)
 W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ]
 0.106 4.74 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000023
_refine_diff_density_max     0.57
_refine_diff_density_min     -0.54
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection
;
 SMART (Siemens, 1993)
;
_computing_cell_refinement
;
 SAINT (Siemens ,1995)
;
_computing_data_reduction
;
 SAINT (Siemens ,1995)
;
_computing_structure_solution
;
 SIR92 (Altomare et al, 1994)
;
_computing_structure_refinement
;
 CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics
;
 CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
 CRYSTALS (Watkin et al 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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
    C C1 0.4931(8) 0.5873(19) 0.727(4) 0.022(5) Uiso 1.0000
    C C2 0.4116(7) 0.6671(15) 0.623(4) 0.020(4) Uiso 1.0000
    C C3 0.3433(8) 0.5274(16) 0.625(6) 0.027(5) Uiso 1.0000
    C C4 0.3644(8) 0.3758(16) 0.443(6) 0.027(4) Uiso 1.0000
    C C5 0.2986(8) 0.2318(17) 0.454(4) 0.025(5) Uiso 1.0000
    N N1 0.4239(7) 0.7498(16) 0.363(4) 0.021(4) Uiso 1.0000
    N N2 0.3051(8) 0.1165(17) 0.257(4) 0.035(4) Uiso 1.0000
    O O1 0.5494(6) 0.5646(14) 0.560(4) 0.037(4) Uiso 1.0000
    O O2 0.2416(6) 0.2346(13) 0.621(4) 0.033(3) Uiso 1.0000
    O O3 0.4911(6) 0.5404(14) 0.963(4) 0.030(4) Uiso 1.0000
    H H10 0.3929 0.7627 0.7414 0.0253 Uiso 1.0000
    H H2 0.3364 0.4834 0.8075 0.0334 Uiso 1.0000
    H H3 0.2894 0.5804 0.5650 0.0334 Uiso 1.0000
    H H8 0.4194 0.3269 0.4969 0.0346 Uiso 1.0000
    H H6 0.3678 0.4189 0.2590 0.0346 Uiso 1.0000
    H H5 0.3529 0.1234 0.1321 0.0427 Uiso 1.0000
    H H4 0.2620 0.0240 0.2366 0.0427 Uiso 1.0000
    H H9 0.4688 0.8387 0.3764 0.0256 Uiso 1.0000
    H H1 0.4403 0.6605 0.2319 0.0256 Uiso 1.0000
    H H7 0.3706 0.8059 0.3064 0.0256 Uiso 1.0000
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.539(9) yes
    C1 O1 . . 1.253(9) yes
    C1 O3 . . 1.258(9) yes
    C2 C3 . . 1.541(9) yes
    C2 N1 . . 1.490(10)
                      yes
    C2 H10 . . 1.002 no
    C3 C4 . . 1.540(10)
                      yes
    C3 H2 . . 1.000 no
    C3 H3 . . 1.003 no
    C4 C5 . . 1.538(9) yes
    C4 H8 . . 0.998 no
    C4 H6 . . 0.996 no
    C5 N2 . . 1.353(9) yes
    C5 O2 . . 1.248(9) yes
    N1 H9 . . 0.999 no
    N1 H1 . . 0.999 no
    N1 H7 . . 1.001 no
    N2 H5 . . 0.996 no
    N2 H4 . . 1.001 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 115.7(14) yes
    C2 C1 O3 . . . 115.0(15) yes
    O1 C1 O3 . . . 128.9(15) yes
    C1 C2 C3 . . . 108.5(11) yes
    C1 C2 N1 . . . 111.6(13) yes
    C3 C2 N1 . . . 113.7(16) yes
    C1 C2 H10 . . . 110.227 no
    C3 C2 H10 . . . 107.833 no
    N1 C2 H10 . . . 104.835 no
    C2 C3 C4 . . . 112.3(13) yes
    C2 C3 H2 . . . 108.811 no
    C4 C3 H2 . . . 108.993 no
    C2 C3 H3 . . . 108.681 no
    C4 C3 H3 . . . 108.736 no
    H2 C3 H3 . . . 109.253 no
    C3 C4 C5 . . . 112.5(12) yes
    C3 C4 H8 . . . 108.557 no
    C5 C4 H8 . . . 108.528 no
    C3 C4 H6 . . . 108.781 no
    C5 C4 H6 . . . 108.550 no
    H8 C4 H6 . . . 109.934 no
    C4 C5 N2 . . . 113.6(14) yes
    C4 C5 O2 . . . 121.1(14) yes
    N2 C5 O2 . . . 125.1(13) yes
    C2 N1 H9 . . . 109.442 no
    C2 N1 H1 . . . 109.414 no
    H9 N1 H1 . . . 109.639 no
    C2 N1 H7 . . . 109.431 no
    H9 N1 H7 . . . 109.417 no
    H1 N1 H7 . . . 109.484 no
    C5 N2 H5 . . . 119.871 no
    C5 N2 H4 . . . 119.858 no
    H5 N2 H4 . . . 120.270 no
data_0.1
_audit_creation_method     CRYSTALS_ver_12.39
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_section_title
; ?
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ? # Footnote for author 1
;
;
 ? # Address for author 1
;
    'Else, S. O.'
;
 ? # Footnote 2
;
;
 ? # Address 2
;
_chemical_name_systematic     ?
_chemical_formula_moiety     'C5 H10 N2 O3'
_chemical_formula_sum     'C5 H10 N2 O3'
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     15.992(2)
_cell_length_b     7.7558(12)
_cell_length_c     5.0941(9)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     631.83(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     551
_cell_measurement_theta_min     2.55
_cell_measurement_theta_max     23.23
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_density_diffrn     1.536
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_F_000     312
_exptl_absorpt_coefficient_mu     0.127
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SORTAV (Blessing)'
_exptl_absorpt_correction_T_min     0.506
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     336
_diffrn_reflns_av_R_equivalents     0.2243
_diffrn_reflns_theta_min     2.547
_diffrn_reflns_theta_max     23.261
_diffrn_reflns_theta_full     17.446
_diffrn_measured_fraction_theta_max     0.569
_diffrn_measured_fraction_theta_full     0.639
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -2
_diffrn_reflns_limit_l_max      2
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     324
_reflns_number_gt     205
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1843
_refine_ls_R_factor_gt     0.1483
_refine_ls_wR_factor_all     0.2840
_refine_ls_wR_factor_gt     0.2568
_refine_ls_wR_factor_ref     0.2840
_refine_ls_goodness_of_fit_ref     1.1595
_refine_ls_number_reflns     267
_refine_ls_number_parameters     41
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 p=P(6)*max(Fo²,0) + (1-P(6))Fc²
 Method = SHELXL 97 (Sheldrick, 1997)
 W = 1. / [Sigma²(F*)+(P(1)p)²+P(2)p+P(4)+P(5)Sin(theta) ]
 P(i) are:
 0.00 11.6 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000024
_refine_diff_density_max     1.01
_refine_diff_density_min     -0.76
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1993)'
_computing_cell_refinement     'SAINT (Siemens ,1995)'
_computing_data_reduction     'SAINT (Siemens ,1995)'
_computing_structure_solution     'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al 2003)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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_disorder_assembly
    _atom_site_disorder_group
    C C1 0.4926(9) 0.586(3) 0.729(5) 0.018(7) Uiso 1.0000 . .
    C C2 0.4111(9) 0.667(2) 0.628(6) 0.015(6) Uiso 1.0000 . .
    C C3 0.3440(11) 0.525(2) 0.630(9) 0.030(7) Uiso 1.0000 . .
    C C4 0.3654(11) 0.376(2) 0.441(9) 0.028(6) Uiso 1.0000 . .
    C C5 0.2979(11) 0.234(2) 0.446(5) 0.026(7) Uiso 1.0000 . .
    N N1 0.4244(9) 0.749(2) 0.368(6) 0.020(5) Uiso 1.0000 . .
    N N2 0.3051(11) 0.117(2) 0.251(6) 0.034(6) Uiso 1.0000 . .
    O O1 0.5492(8) 0.5668(19) 0.563(5) 0.031(5) Uiso 1.0000 . .
    O O2 0.2407(8) 0.2361(18) 0.612(5) 0.031(5) Uiso 1.0000 . .
    O O3 0.4924(8) 0.541(2) 0.965(5) 0.025(5) Uiso 1.0000 . .
    H H10 0.3914 0.7632 0.7434 0.0183 Uiso 1.0000 . .
    H H2 0.3391 0.4779 0.8119 0.0364 Uiso 1.0000 . .
    H H3 0.2893 0.5764 0.5756 0.0364 Uiso 1.0000 . .
    H H8 0.4201 0.3241 0.4950 0.0332 Uiso 1.0000 . .
    H H6 0.3701 0.4224 0.2588 0.0332 Uiso 1.0000 . .
    H H5 0.3530 0.1239 0.1251 0.0410 Uiso 1.0000 . .
    H H4 0.2627 0.0229 0.2331 0.0410 Uiso 1.0000 . .
    H H9 0.4687 0.8399 0.3830 0.0242 Uiso 1.0000 . .
    H H1 0.4424 0.6601 0.2380 0.0242 Uiso 1.0000 . .
    H H7 0.3710 0.8036 0.3072 0.0242 Uiso 1.0000 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.538(9) yes
    C1 O1 . . 1.246(9) yes
    C1 O3 . . 1.249(10) yes
    C2 C3 . . 1.539(9) yes
    C2 N1 . . 1.487(10) yes
    C2 H10 . . 1.000 no
    C3 C4 . . 1.542(10) yes
    C3 H2 . . 1.000 no
    C3 H3 . . 1.000 no
    C4 C5 . . 1.540(9) yes
    C4 H8 . . 1.000 no
    C4 H6 . . 1.000 no
    C5 N2 . . 1.350(10) yes
    C5 O2 . . 1.246(10) yes
    N1 H9 . . 1.000 no
    N1 H1 . . 1.000 no
    N1 H7 . . 1.000 no
    N2 H5 . . 1.000 no
    N2 H4 . . 1.000 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 115.9(18) yes
    C2 C1 O3 . . . 115.7(19) yes
    O1 C1 O3 . . . 128.3(19) yes
    C1 C2 C3 . . . 107.2(14) yes
    C1 C2 N1 . . . 110.7(18) yes
    C3 C2 N1 . . . 114(2) yes
    C1 C2 H10 . . . 112.008 no
    C3 C2 H10 . . . 108.146 no
    N1 C2 H10 . . . 104.459 no
    C2 C3 C4 . . . 112.3(18) yes
    C2 C3 H2 . . . 108.754 no
    C4 C3 H2 . . . 108.765 no
    C2 C3 H3 . . . 108.757 no
    C4 C3 H3 . . . 108.765 no
    H2 C3 H3 . . . 109.462 no
    C3 C4 C5 . . . 111.7(17) yes
    C3 C4 H8 . . . 108.894 no
    C5 C4 H8 . . . 108.904 no
    C3 C4 H6 . . . 108.896 no
    C5 C4 H6 . . . 108.909 no
    H8 C4 H6 . . . 109.470 no
    C4 C5 N2 . . . 114.(2)   yes
    C4 C5 O2 . . . 121.(2)   yes
    N2 C5 O2 . . . 124.7(17) yes
    C2 N1 H9 . . . 109.470 no
    C2 N1 H1 . . . 109.467 no
    H9 N1 H1 . . . 109.480 no
    C2 N1 H7 . . . 109.463 no
    H9 N1 H7 . . . 109.474 no
    H1 N1 H7 . . . 109.473 no
    C5 N2 H5 . . . 120.002 no
    C5 N2 H4 . . . 120.000 no
    H5 N2 H4 . . . 119.998 no
data_0.8
_audit_creation_method     CRYSTALS_ver_12-03-99
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_address
;
;
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '01316504804'
_publ_section_title
;
 ?                                     # Title of paper
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ?                                                #footnote for author 1
;
;
 ?                                                # Address for author 1
;
    'Else, S. O.'
;
 ?                                                # footnote 2
;
;
 ?                                                # Address 2
;
_chemical_name_systematic
;
?
;
_chemical_formula_moiety     ' C5 H10 N2 O3 '
_chemical_formula_sum     ' C5 H10 N2 O3 '
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     15.879(6)
_cell_length_b     7.705(3)
_cell_length_c     5.084(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     622.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     347
_cell_measurement_theta_min     2.57
_cell_measurement_theta_max     22.49
_cell_measurement_temperature     293
_exptl_crystal_description     ' block '
_exptl_crystal_colour     ' colourless '
_exptl_crystal_size_max     'not measured'
_exptl_crystal_size_mid     'not measured'
_exptl_crystal_size_min     'not measured'
_exptl_crystal_density_diffrn     1.561
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_F_000     312.000
_exptl_absorpt_coefficient_mu     0.129
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SORTAV (Blessing)
;
_exptl_absorpt_correction_T_min     0.487
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     341
_diffrn_reflns_av_R_equivalents     0.1846
_diffrn_reflns_theta_min     2.565
_diffrn_reflns_theta_max     23.397
_diffrn_reflns_theta_full     17.665
_diffrn_measured_fraction_theta_max     0.581
_diffrn_measured_fraction_theta_full     0.659
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -3
_diffrn_reflns_limit_l_max     3
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0.00
_reflns_number_total     330
_reflns_number_gt     206
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1827
_refine_ls_R_factor_gt     0.1147
_refine_ls_wR_factor_all     0.2489
_refine_ls_wR_factor_gt     0.2115
_refine_ls_wR_factor_ref     0.2489
_refine_ls_goodness_of_fit_ref     1.0373
_refine_ls_number_reflns     330
_refine_ls_number_parameters     41
_refine_ls_hydrogen_treatment     fixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = SHELXL 97 (Sheldrick, 1997)
 W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ]
 0.550E-01 5.43 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000041
_refine_diff_density_max     0.71
_refine_diff_density_min     -0.76
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection
;
 SMART (Siemens, 1993)
;
_computing_cell_refinement
;
 SAINT (Siemens ,1995)
;
_computing_data_reduction
;
 SAINT (Siemens ,1995)
;
_computing_structure_solution
;
 SIR92 (Altomare et al, 1994)
;
_computing_structure_refinement
;
 CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics
;
 CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
 CRYSTALS (Watkin et al 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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
    C C1 0.4945(7) 0.593(2) 0.730(4) 0.025(5) Uiso 1.0000
    C C2 0.4114(7) 0.6734(16) 0.633(5) 0.026(5) Uiso 1.0000
    C C3 0.3423(7) 0.5337(17) 0.619(6) 0.029(4) Uiso 1.0000
    C C4 0.3646(8) 0.3792(16) 0.440(6) 0.028(4) Uiso 1.0000
    C C5 0.2980(7) 0.2350(18) 0.454(4) 0.027(4) Uiso 1.0000
    N N1 0.4219(6) 0.7551(16) 0.370(4) 0.025(3) Uiso 1.0000
    N N2 0.3047(7) 0.1155(17) 0.260(4) 0.033(4) Uiso 1.0000
    O O1 0.5514(6) 0.5689(13) 0.566(4) 0.035(3) Uiso 1.0000
    O O2 0.2425(6) 0.2336(13) 0.628(4) 0.034(3) Uiso 1.0000
    O O3 0.4918(6) 0.5443(14) 0.965(4) 0.030(3) Uiso 1.0000
    H H10 0.3945 0.7654 0.7618 0.0316 Uiso 1.0000
    H H2 0.3321 0.4888 0.8007 0.0344 Uiso 1.0000
    H H3 0.2897 0.5889 0.5504 0.0344 Uiso 1.0000
    H H8 0.4201 0.3306 0.4968 0.0341 Uiso 1.0000
    H H6 0.3687 0.4211 0.2546 0.0341 Uiso 1.0000
    H H5 0.3510 0.1248 0.1279 0.0397 Uiso 1.0000
    H H4 0.2634 0.0178 0.2498 0.0397 Uiso 1.0000
    H H9 0.4668 0.8460 0.3793 0.0303 Uiso 1.0000
    H H1 0.4384 0.6645 0.2390 0.0303 Uiso 1.0000
    H H7 0.3675 0.8098 0.3150 0.0303 Uiso 1.0000
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.538(9) yes
    C1 O1 . . 1.246(9) yes
    C1 O3 . . 1.252(9) yes
    C2 C3 . . 1.539(9) yes
    C2 N1 . . 1.490(10)
                      yes
    C2 H10 . . 1.000 no
    C3 C4 . . 1.540(10)
                      yes
    C3 H2 . . 1.001 no
    C3 H3 . . 0.999 no
    C4 C5 . . 1.536(9) yes
    C4 H8 . . 1.000 no
    C4 H6 . . 1.000 no
    C5 N2 . . 1.353(9) yes
    C5 O2 . . 1.247(9) yes
    N1 H9 . . 1.000 no
    N1 H1 . . 1.000 no
    N1 H7 . . 1.001 no
    N2 H5 . . 0.999 no
    N2 H4 . . 1.000 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 117.8(14) yes
    C2 C1 O3 . . . 113.4(14) yes
    O1 C1 O3 . . . 128.3(14) yes
    C1 C2 C3 . . . 110.2(11) yes
    C1 C2 N1 . . . 111.3(13) yes
    C3 C2 N1 . . . 109.4(16) yes
    C1 C2 H10 . . . 107.791 no
    C3 C2 H10 . . . 109.652 no
    N1 C2 H10 . . . 108.499 no
    C2 C3 C4 . . . 114.0(13) yes
    C2 C3 H2 . . . 108.241 no
    C4 C3 H2 . . . 108.314 no
    C2 C3 H3 . . . 108.397 no
    C4 C3 H3 . . . 108.426 no
    H2 C3 H3 . . . 109.406 no
    C3 C4 C5 . . . 112.0(12) yes
    C3 C4 H8 . . . 108.835 no
    C5 C4 H8 . . . 108.859 no
    C3 C4 H6 . . . 108.759 no
    C5 C4 H6 . . . 108.819 no
    H8 C4 H6 . . . 109.514 no
    C4 C5 N2 . . . 113.8(13) yes
    C4 C5 O2 . . . 121.7(15) yes
    N2 C5 O2 . . . 124.4(12) yes
    C2 N1 H9 . . . 109.506 no
    C2 N1 H1 . . . 109.491 no
    H9 N1 H1 . . . 109.471 no
    C2 N1 H7 . . . 109.497 no
    H9 N1 H7 . . . 109.452 no
    H1 N1 H7 . . . 109.411 no
    C5 N2 H5 . . . 120.018 no
    C5 N2 H4 . . . 119.938 no
    H5 N2 H4 . . . 120.044 no
data_1.4
_audit_creation_method     CRYSTALS_ver_12-03-99
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_address
;
Chemical Crystallography Laboratory
9 Parks Road
OXFORD OX1 3PD
;
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '01316504804'
_publ_section_title
;
 ?                                     # Title of paper
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ?                                                #footnote for author 1
;
;
 ?                                                # Address for author 1
;
    'Else, S. O.'
;
 ?                                                # footnote 2
;
;
 ?                                                # Address 2
;
_chemical_name_systematic
;
?
;
_chemical_formula_moiety     ' C5 H10 N2 O3 '
_chemical_formula_sum     ' C5 H10 N2 O3 '
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     15.679(11)
_cell_length_b     7.628(6)
_cell_length_c     5.023(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     600.8(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     313
_cell_measurement_theta_min     2.59
_cell_measurement_theta_max     23.56
_cell_measurement_temperature     293
_exptl_crystal_description     ' block '
_exptl_crystal_colour     ' colourless '
_exptl_crystal_size_max     'not measured'
_exptl_crystal_size_mid     'not measured'
_exptl_crystal_size_min     'not measured'
_exptl_crystal_density_diffrn     1.616
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_F_000     312.000
_exptl_absorpt_coefficient_mu     0.133
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SORTAV (Blessing)
;
_exptl_absorpt_correction_T_min     0.657
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     305
_diffrn_reflns_av_R_equivalents     0.1554
_diffrn_reflns_theta_min     2.598
_diffrn_reflns_theta_max     23.322
_diffrn_reflns_theta_full     17.608
_diffrn_measured_fraction_theta_max     0.541
_diffrn_measured_fraction_theta_full     0.625
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -2
_diffrn_reflns_limit_l_max     2
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0.00
_reflns_number_total     295
_reflns_number_gt     202
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1541
_refine_ls_R_factor_gt     0.1073
_refine_ls_wR_factor_all     0.2431
_refine_ls_wR_factor_gt     0.2232
_refine_ls_wR_factor_ref     0.2431
_refine_ls_goodness_of_fit_ref     1.0409
_refine_ls_number_reflns     295
_refine_ls_number_parameters     41
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = SHELXL 97 (Sheldrick, 1997)
 W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ]
 0.897E-01 4.49 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000042
_refine_diff_density_max     0.76
_refine_diff_density_min     -0.55
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection
;
 SMART (Siemens, 1993)
;
_computing_cell_refinement
;
 SAINT (Siemens ,1995)
;
_computing_data_reduction
;
 SAINT (Siemens ,1995)
;
_computing_structure_solution
;
 SIR92 (Altomare et al, 1994)
;
_computing_structure_refinement
;
 CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics
;
 CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
 CRYSTALS (Watkin et al 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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
    C C1 0.4947(7) 0.597(2) 0.733(4) 0.022(4) Uiso 1.0000
    C C2 0.4109(7) 0.6788(15) 0.636(4) 0.019(4) Uiso 1.0000
    C C3 0.3417(7) 0.5369(15) 0.624(6) 0.020(4) Uiso 1.0000
    C C4 0.3634(8) 0.3816(15) 0.441(6) 0.021(4) Uiso 1.0000
    C C5 0.2976(8) 0.2333(18) 0.459(4) 0.023(4) Uiso 1.0000
    N N1 0.4212(7) 0.7622(16) 0.370(4) 0.024(3) Uiso 1.0000
    N N2 0.3039(7) 0.1159(17) 0.260(4) 0.034(4) Uiso 1.0000
    O O1 0.5524(6) 0.5745(13) 0.565(4) 0.033(3) Uiso 1.0000
    O O2 0.2428(6) 0.2347(13) 0.637(4) 0.033(3) Uiso 1.0000
    O O3 0.4939(6) 0.5498(14) 0.972(4) 0.032(4) Uiso 1.0000
    H H10 0.3938 0.7725 0.7643 0.0223 Uiso 1.0000
    H H2 0.3327 0.4907 0.8080 0.0237 Uiso 1.0000
    H H3 0.2879 0.5921 0.5582 0.0237 Uiso 1.0000
    H H8 0.4206 0.3344 0.4925 0.0251 Uiso 1.0000
    H H6 0.3656 0.4245 0.2527 0.0251 Uiso 1.0000
    H H5 0.3508 0.1266 0.1256 0.0407 Uiso 1.0000
    H H4 0.2617 0.0181 0.2456 0.0407 Uiso 1.0000
    H H9 0.4664 0.8544 0.3797 0.0285 Uiso 1.0000
    H H1 0.4381 0.6713 0.2365 0.0285 Uiso 1.0000
    H H7 0.3660 0.8169 0.3148 0.0285 Uiso 1.0000
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.533(9) yes
    C1 O1 . . 1.250(9) yes
    C1 O3 . . 1.253(9) yes
    C2 C3 . . 1.533(9) yes
    C2 N1 . . 1.490(10)
                      yes
    C2 H10 . . 1.000 no
    C3 C4 . . 1.540(10)
                      yes
    C3 H2 . . 1.001 no
    C3 H3 . . 1.000 no
    C4 C5 . . 1.534(9) yes
    C4 H8 . . 1.000 no
    C4 H6 . . 1.000 no
    C5 N2 . . 1.350(10)
                      yes
    C5 O2 . . 1.241(9) yes
    N1 H9 . . 1.000 no
    N1 H1 . . 1.000 no
    N1 H7 . . 1.000 no
    N2 H5 . . 1.000 no
    N2 H4 . . 1.000 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 117.4(13) yes
    C2 C1 O3 . . . 114.5(14) yes
    O1 C1 O3 . . . 127.9(14) yes
    C1 C2 C3 . . . 109.4(10) yes
    C1 C2 N1 . . . 111.5(13) yes
    C3 C2 N1 . . . 110.0(15) yes
    C1 C2 H10 . . . 108.333 no
    C3 C2 H10 . . . 109.863 no
    N1 C2 H10 . . . 107.637 no
    C2 C3 C4 . . . 114.3(12) yes
    C2 C3 H2 . . . 108.235 no
    C4 C3 H2 . . . 108.238 no
    C2 C3 H3 . . . 108.293 no
    C4 C3 H3 . . . 108.305 no
    H2 C3 H3 . . . 109.452 no
    C3 C4 C5 . . . 112.5(12) yes
    C3 C4 H8 . . . 108.710 no
    C5 C4 H8 . . . 108.699 no
    C3 C4 H6 . . . 108.665 no
    C5 C4 H6 . . . 108.702 no
    H8 C4 H6 . . . 109.481 no
    C4 C5 N2 . . . 113.4(13) yes
    C4 C5 O2 . . . 120.2(14) yes
    N2 C5 O2 . . . 126.3(12) yes
    C2 N1 H9 . . . 109.453 no
    C2 N1 H1 . . . 109.471 no
    H9 N1 H1 . . . 109.492 no
    C2 N1 H7 . . . 109.450 no
    H9 N1 H7 . . . 109.469 no
    H1 N1 H7 . . . 109.492 no
    C5 N2 H5 . . . 120.000 no
    C5 N2 H4 . . . 120.007 no
    H5 N2 H4 . . . 119.993 no
data_2.7
_audit_creation_method     CRYSTALS_ver_12-03-99
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_address
;
Chemical Crystallography Laboratory
9 Parks Road
OXFORD OX1 3PD
;
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '01316504804'
_publ_section_title
;
 ?                                     # Title of paper
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ?                                                #footnote for author 1
;
;
 ?                                                # Address for author 1
;
    'Else, S. O.'
;
 ?                                                # footnote 2
;
;
 ?                                                # Address 2
;
_chemical_name_systematic
;
?
;
_chemical_formula_moiety     ' C5 H10 N2 O3 '
_chemical_formula_sum     ' C5 H10 N2 O3 '
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     15.450(8)
_cell_length_b     7.550(6)
_cell_length_c     4.972(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     580.0(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     325
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     21.31
_cell_measurement_temperature     293
_exptl_crystal_description     ' block '
_exptl_crystal_colour     ' colourless '
_exptl_crystal_size_max     'not measured'
_exptl_crystal_size_mid     'not measured'
_exptl_crystal_size_min     'not measured'
_exptl_crystal_density_diffrn     1.674
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_F_000     312.000
_exptl_absorpt_coefficient_mu     0.138
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SORTAV (Blessing)
;
_exptl_absorpt_correction_T_min     0.557
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     281
_diffrn_reflns_av_R_equivalents     0.1397
_diffrn_reflns_theta_min     2.637
_diffrn_reflns_theta_max     23.315
_diffrn_reflns_theta_full     17.544
_diffrn_measured_fraction_theta_max     0.512
_diffrn_measured_fraction_theta_full     0.614
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -3
_diffrn_reflns_limit_l_max     3
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0.00
_reflns_number_total     271
_reflns_number_gt     190
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1119
_refine_ls_R_factor_gt     0.0773
_refine_ls_wR_factor_all     0.1776
_refine_ls_wR_factor_gt     0.1639
_refine_ls_wR_factor_ref     0.1776
_refine_ls_goodness_of_fit_ref     1.0206
_refine_ls_number_reflns     271
_refine_ls_number_parameters     41
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = SHELXL 97 (Sheldrick, 1997)
 W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ]
 0.622E-01 1.70 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000028
_refine_diff_density_max     0.40
_refine_diff_density_min     -0.39
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection
;
 SMART (Siemens, 1993)
;
_computing_cell_refinement
;
 SAINT (Siemens ,1995)
;
_computing_data_reduction
;
 SAINT (Siemens ,1995)
;
_computing_structure_solution
;
 SIR92 (Altomare et al, 1994)
;
_computing_structure_refinement
;
 CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics
;
 CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
 CRYSTALS (Watkin et al 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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
    C C1 0.4937(6) 0.6050(16) 0.735(3) 0.029(4) Uiso 1.0000
    C C2 0.4085(6) 0.6870(13) 0.634(4) 0.032(4) Uiso 1.0000
    C C3 0.3404(5) 0.5398(13) 0.629(4) 0.024(3) Uiso 1.0000
    C C4 0.3647(6) 0.3874(13) 0.437(5) 0.030(3) Uiso 1.0000
    C C5 0.2993(6) 0.2369(14) 0.458(3) 0.025(3) Uiso 1.0000
    N N1 0.4205(5) 0.7699(13) 0.366(3) 0.030(3) Uiso 1.0000
    N N2 0.3023(5) 0.1196(13) 0.254(3) 0.033(3) Uiso 1.0000
    O O1 0.5533(4) 0.5850(10)
                            0.570(3) 0.037(3) Uiso 1.0000
    O O2 0.2466(5) 0.2320(10)
                            0.647(3) 0.041(3) Uiso 1.0000
    O O3 0.4944(5) 0.5602(11) 0.977(3) 0.037(3) Uiso 1.0000
    H H10 0.3910 0.7849 0.7578 0.0382 Uiso 1.0000
    H H2 0.3318 0.4945 0.8131 0.0263 Uiso 1.0000
    H H3 0.2841 0.5949 0.5629 0.0263 Uiso 1.0000
    H H8 0.4232 0.3430 0.4913 0.0349 Uiso 1.0000
    H H6 0.3668 0.4331 0.2495 0.0349 Uiso 1.0000
    H H5 0.3470 0.1340 0.1091 0.0405 Uiso 1.0000
    H H4 0.2616 0.0175 0.2493 0.0405 Uiso 1.0000
    H H9 0.4653 0.8639 0.3743 0.0367 Uiso 1.0000
    H H1 0.4379 0.6773 0.2318 0.0367 Uiso 1.0000
    H H7 0.3638 0.8237 0.3061 0.0367 Uiso 1.0000
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.539(9) yes
    C1 O1 . . 1.243(9) yes
    C1 O3 . . 1.250(9) yes
    C2 C3 . . 1.531(8) yes
    C2 N1 . . 1.486(9) yes
    C2 H10 . . 0.999 no
    C3 C4 . . 1.541(9) yes
    C3 H2 . . 0.987 no
    C3 H3 . . 1.018 no
    C4 C5 . . 1.525(8) yes
    C4 H8 . . 1.000 no
    C4 H6 . . 0.995 no
    C5 N2 . . 1.348(9) yes
    C5 O2 . . 1.243(9) yes
    N1 H9 . . 0.993 no
    N1 H1 . . 1.003 no
    N1 H7 . . 1.009 no
    N2 H5 . . 1.004 no
    N2 H4 . . 0.995 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 117.8(11) yes
    C2 C1 O3 . . . 115.6(11) yes
    O1 C1 O3 . . . 126.6(11) yes
    C1 C2 C3 . . . 107.6(8) yes
    C1 C2 N1 . . . 110.9(10) yes
    C3 C2 N1 . . . 112.1(12) yes
    C1 C2 H10 . . . 109.133 no
    C3 C2 H10 . . . 111.217 no
    N1 C2 H10 . . . 105.935 no
    C2 C3 C4 . . . 112.6(9) yes
    C2 C3 H2 . . . 109.113 no
    C4 C3 H2 . . . 110.368 no
    C2 C3 H3 . . . 107.239 no
    C4 C3 H3 . . . 108.339 no
    H2 C3 H3 . . . 109.039 no
    C3 C4 C5 . . . 110.6(9) yes
    C3 C4 H8 . . . 107.673 no
    C5 C4 H8 . . . 109.345 no
    C3 C4 H6 . . . 109.185 no
    C5 C4 H6 . . . 110.200 no
    H8 C4 H6 . . . 109.810 no
    C4 C5 N2 . . . 114.4(11) yes
    C4 C5 O2 . . . 120.6(11) yes
    N2 C5 O2 . . . 124.9(10) yes
    C2 N1 H9 . . . 110.474 no
    C2 N1 H1 . . . 109.679 no
    H9 N1 H1 . . . 109.837 no
    C2 N1 H7 . . . 109.025 no
    H9 N1 H7 . . . 109.276 no
    H1 N1 H7 . . . 108.516 no
    C5 N2 H5 . . . 119.622 no
    C5 N2 H4 . . . 120.283 no
    H5 N2 H4 . . . 120.074 no
data_3.6
_audit_creation_method     CRYSTALS_ver_12-03-99
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_address
;
Chemical Crystallography Laboratory
9 Parks Road
OXFORD OX1 3PD
;
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '01316504804'
_publ_section_title
;
 ?                                     # Title of paper
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ?                                                #footnote for author 1
;
;
 ?                                                # Address for author 1
;
    'Else, S. O.'
;
 ?                                                # footnote 2
;
;
 ?                                                # Address 2
;
_chemical_name_systematic
;
?
;
_chemical_formula_moiety     ' C5 H10 N2 O3 '
_chemical_formula_sum     ' C5 H10 N2 O3 '
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     15.328(7)
_cell_length_b     7.497(5)
_cell_length_c     4.941(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     567.8(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     384
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     23.13
_cell_measurement_temperature     293
_exptl_crystal_description     ' block '
_exptl_crystal_colour     ' colourless '
_exptl_crystal_size_max     'not measured'
_exptl_crystal_size_mid     'not measured'
_exptl_crystal_size_min     'not measured'
_exptl_crystal_density_diffrn     1.710
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_F_000     312.000
_exptl_absorpt_coefficient_mu     0.141
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SORTAV (Blessing)
;
_exptl_absorpt_correction_T_min     0.307
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     281
_diffrn_reflns_av_R_equivalents     0.1442
_diffrn_reflns_theta_min     2.658
_diffrn_reflns_theta_max     23.407
_diffrn_reflns_theta_full     17.614
_diffrn_measured_fraction_theta_max     0.517
_diffrn_measured_fraction_theta_full     0.611
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -2
_diffrn_reflns_limit_l_max     2
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0.00
_reflns_number_total     270
_reflns_number_gt     196
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1362
_refine_ls_R_factor_gt     0.0909
_refine_ls_wR_factor_all     0.1881
_refine_ls_wR_factor_gt     0.1810
_refine_ls_wR_factor_ref     0.1881
_refine_ls_goodness_of_fit_ref     1.0930
_refine_ls_number_reflns     270
_refine_ls_number_parameters     41
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = SHELXL 97 (Sheldrick, 1997)
 W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ]
 0.344E-01 3.13 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000043
_refine_diff_density_max     0.53
_refine_diff_density_min     -0.54
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection
;
 SMART (Siemens, 1993)
;
_computing_cell_refinement
;
 SAINT (Siemens ,1995)
;
_computing_data_reduction
;
 SAINT (Siemens ,1995)
;
_computing_structure_solution
;
 SIR92 (Altomare et al, 1994)
;
_computing_structure_refinement
;
 CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics
;
 CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
 CRYSTALS (Watkin et al 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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
    C C1 0.4949(7) 0.6128(18) 0.733(3) 0.033(4) Uiso 1.0000
    C C2 0.4084(6) 0.6919(15) 0.637(4) 0.030(4) Uiso 1.0000
    C C3 0.3396(6) 0.5435(14) 0.630(5) 0.018(3) Uiso 1.0000
    C C4 0.3644(7) 0.3933(14) 0.432(5) 0.026(4) Uiso 1.0000
    C C5 0.3005(7) 0.2389(15) 0.468(3) 0.025(4) Uiso 1.0000
    N N1 0.4184(6) 0.7714(15) 0.363(4) 0.029(3) Uiso 1.0000
    N N2 0.3014(6) 0.1220(14) 0.262(3) 0.030(3) Uiso 1.0000
    O O1 0.5543(5) 0.5883(12) 0.566(4) 0.041(3) Uiso 1.0000
    O O2 0.2478(5) 0.2330(12) 0.657(3) 0.039(3) Uiso 1.0000
    O O3 0.4952(5) 0.5638(13) 0.975(3) 0.033(3) Uiso 1.0000
    H H10 0.3900 0.7874 0.7656 0.0369 Uiso 1.0000
    H H2 0.3334 0.4916 0.8149 0.0210 Uiso 1.0000
    H H3 0.2826 0.5961 0.5713 0.0210 Uiso 1.0000
    H H8 0.4251 0.3516 0.4703 0.0311 Uiso 1.0000
    H H6 0.3611 0.4385 0.2414 0.0311 Uiso 1.0000
    H H5 0.3460 0.1342 0.1149 0.0370 Uiso 1.0000
    H H4 0.2578 0.0232 0.2554 0.0370 Uiso 1.0000
    H H9 0.4633 0.8676 0.3692 0.0349 Uiso 1.0000
    H H1 0.4369 0.6768 0.2323 0.0349 Uiso 1.0000
    H H7 0.3612 0.8225 0.3039 0.0349 Uiso 1.0000
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.528(9) yes
    C1 O1 . . 1.243(9) yes
    C1 O3 . . 1.247(9) yes
    C2 C3 . . 1.533(9) yes
    C2 N1 . . 1.490(10)
                      yes
    C2 H10 . . 0.998 no
    C3 C4 . . 1.540(10)
                      yes
    C3 H2 . . 0.998 no
    C3 H3 . . 1.001 no
    C4 C5 . . 1.526(9) yes
    C4 H8 . . 0.999 no
    C4 H6 . . 1.004 no
    C5 N2 . . 1.342(9) yes
    C5 O2 . . 1.238(9) yes
    N1 H9 . . 0.997 no
    N1 H1 . . 1.000 no
    N1 H7 . . 1.001 no
    N2 H5 . . 1.001 no
    N2 H4 . . 0.998 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 119.0(12) yes
    C2 C1 O3 . . . 114.6(12) yes
    O1 C1 O3 . . . 126.1(13) yes
    C1 C2 C3 . . . 108.8(10) yes
    C1 C2 N1 . . . 110.5(11) yes
    C3 C2 N1 . . . 109.9(12) yes
    C1 C2 H10 . . . 108.962 no
    C3 C2 H10 . . . 109.916 no
    N1 C2 H10 . . . 108.713 no
    C2 C3 C4 . . . 112.1(10) yes
    C2 C3 H2 . . . 109.164 no
    C4 C3 H2 . . . 108.641 no
    C2 C3 H3 . . . 108.728 no
    C4 C3 H3 . . . 108.637 no
    H2 C3 H3 . . . 109.542 no
    C3 C4 C5 . . . 108.9(10) yes
    C3 C4 H8 . . . 109.827 no
    C5 C4 H8 . . . 109.824 no
    C3 C4 H6 . . . 109.670 no
    C5 C4 H6 . . . 109.337 no
    H8 C4 H6 . . . 109.219 no
    C4 C5 N2 . . . 113.7(11) yes
    C4 C5 O2 . . . 122.2(12) yes
    N2 C5 O2 . . . 123.8(10) yes
    C2 N1 H9 . . . 109.457 no
    C2 N1 H1 . . . 109.391 no
    H9 N1 H1 . . . 109.696 no
    C2 N1 H7 . . . 109.197 no
    H9 N1 H7 . . . 109.686 no
    H1 N1 H7 . . . 109.398 no
    C5 N2 H5 . . . 119.781 no
    C5 N2 H4 . . . 120.139 no
    H5 N2 H4 . . . 120.080 no
data_4.9
_audit_creation_method     CRYSTALS_ver_12-03-99
_journal_date_recd_electronic     2008-02-13
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     466
_journal_page_last     475
_journal_paper_category     FA
_journal_coeditor_code     BM5054
_publ_contact_author_name     'Patricia Lozano-Casal'
_publ_contact_author_address
;
Chemical Crystallography Laboratory
9 Parks Road
OXFORD OX1 3PD
;
_publ_contact_author_email     'P.Lozano-Casal@ed.ac.uk'
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '01316504804'
_publ_section_title
;
 ?                                     # Title of paper
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Other, Anthony N.'
;
 ?                                                #footnote for author 1
;
;
 ?                                                # Address for author 1
;
    'Else, S. O.'
;
 ?                                                # footnote 2
;
;
 ?                                                # Address 2
;
_chemical_name_systematic
;
?
;
_chemical_formula_moiety     ' C5 H10 N2 O3 '
_chemical_formula_sum     ' C5 H10 N2 O3 '
_chemical_formula_weight     146.15
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     15.191(8)
_cell_length_b     7.455(5)
_cell_length_c     4.882(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     552.8(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     190
_cell_measurement_theta_min     5.37
_cell_measurement_theta_max     22.51
_cell_measurement_temperature     293
_exptl_crystal_description     ' block '
_exptl_crystal_colour     ' colourless '
_exptl_crystal_size_max     0.00
_exptl_crystal_size_mid     0.00
_exptl_crystal_size_min     0.00
_exptl_crystal_density_diffrn     1.756
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     312.000
_exptl_absorpt_coefficient_mu     0.145
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SORTAV (Blessing)
;
_exptl_absorpt_correction_T_min     0.722
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART
;
_diffrn_measurement_method     'φ & ω scans'
_diffrn_reflns_number     292
_diffrn_reflns_av_R_equivalents     0.2135
_diffrn_reflns_theta_min     2.682
_diffrn_reflns_theta_max     23.238
_diffrn_reflns_theta_full     17.545
_diffrn_measured_fraction_theta_max     0.566
_diffrn_measured_fraction_theta_full     0.664
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -3
_diffrn_reflns_limit_l_max     3
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0.00
_reflns_number_total     283
_reflns_number_gt     182
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1658
_refine_ls_R_factor_gt     0.1143
_refine_ls_wR_factor_all     0.1827
_refine_ls_wR_factor_gt     0.1707
_refine_ls_wR_factor_ref     0.1827
_refine_ls_goodness_of_fit_ref     1.0975
_refine_ls_number_reflns     278
_refine_ls_number_parameters     41
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = SHELXL 97 (Sheldrick, 1997)
 W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ]
 0.00 3.26 0.00 0.00 0.00 0.333
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000027
_refine_diff_density_max     1.00
_refine_diff_density_min     -1.05
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection
;
 SMART (Siemens, 1993)
;
_computing_cell_refinement
;
 SAINT (Siemens ,1995)
;
_computing_data_reduction
;
 SAINT (Siemens ,1995)
;
_computing_structure_solution
;
 SIR92 (Altomare et al, 1994)
;
_computing_structure_refinement
;
 CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics
;
 CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
 CRYSTALS (Watkin et al 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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
    C C1 0.4946(8) 0.619(2) 0.736(4) 0.025(5) Uiso 1.0000
    C C2 0.4083(8) 0.6962(17) 0.623(5) 0.028(5) Uiso 1.0000
    C C3 0.3386(8) 0.5471(16) 0.625(5) 0.024(5) Uiso 1.0000
    C C4 0.3657(8) 0.3955(16) 0.429(5) 0.019(4) Uiso 1.0000
    C C5 0.2995(9) 0.2424(18) 0.468(4) 0.029(5) Uiso 1.0000
    N N1 0.4169(8) 0.7804(18) 0.348(5) 0.033(4) Uiso 1.0000
    N N2 0.3006(8) 0.1232(18) 0.260(4) 0.032(4) Uiso 1.0000
    O O1 0.5562(6) 0.5959(14) 0.569(4) 0.033(3) Uiso 1.0000
    O O2 0.2504(7) 0.2316(14) 0.673(4) 0.037(4) Uiso 1.0000
    O O3 0.4959(6) 0.5678(16) 0.980(4) 0.038(4) Uiso 1.0000
    H H10 0.3898 0.7972 0.7446 0.0336 Uiso 1.0000
    H H2 0.3330 0.4979 0.8151 0.0286 Uiso 1.0000
    H H3 0.2807 0.5978 0.5658 0.0286 Uiso 1.0000
    H H8 0.4265 0.3532 0.4731 0.0225 Uiso 1.0000
    H H6 0.3639 0.4392 0.2350 0.0225 Uiso 1.0000
    H H5 0.3419 0.1409 0.1022 0.0389 Uiso 1.0000
    H H4 0.2603 0.0172 0.2626 0.0389 Uiso 1.0000
    H H9 0.4628 0.8765 0.3552 0.0400 Uiso 1.0000
    H H1 0.4345 0.6873 0.2112 0.0400 Uiso 1.0000
    H H7 0.3592 0.8341 0.2934 0.0400 Uiso 1.0000
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.535(9) yes
    C1 O1 . . 1.253(9) yes
    C1 O3 . . 1.252(9) yes
    C2 C3 . . 1.535(9) yes
    C2 N1 . . 1.490(10)
                      yes
    C2 H10 . . 1.000 no
    C3 C4 . . 1.539(9) yes
    C3 H2 . . 1.000 no
    C3 H3 . . 1.000 no
    C4 C5 . . 1.534(9) yes
    C4 H8 . . 1.000 no
    C4 H6 . . 1.000 no
    C5 N2 . . 1.351(9) yes
    C5 O2 . . 1.249(9) yes
    N1 H9 . . 1.000 no
    N1 H1 . . 1.000 no
    N1 H7 . . 1.000 no
    N2 H5 . . 1.000 no
    N2 H4 . . 1.000 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 117.0(14) yes
    C2 C1 O3 . . . 118.1(14) yes
    O1 C1 O3 . . . 124.5(15) yes
    C1 C2 C3 . . . 108.3(11) yes
    C1 C2 N1 . . . 114.1(14) yes
    C3 C2 N1 . . . 112.0(14) yes
    C1 C2 H10 . . . 107.961 no
    C3 C2 H10 . . . 110.293 no
    N1 C2 H10 . . . 104.045 no
    C2 C3 C4 . . . 110.0(12) yes
    C2 C3 H2 . . . 109.354 no
    C4 C3 H2 . . . 109.341 no
    C2 C3 H3 . . . 109.328 no
    C4 C3 H3 . . . 109.321 no
    H2 C3 H3 . . . 109.472 no
    C3 C4 C5 . . . 107.0(11) yes
    C3 C4 H8 . . . 110.076 no
    C5 C4 H8 . . . 110.072 no
    C3 C4 H6 . . . 110.086 no
    C5 C4 H6 . . . 110.072 no
    H8 C4 H6 . . . 109.458 no
    C4 C5 N2 . . . 112.7(12) yes
    C4 C5 O2 . . . 122.6(13) yes
    N2 C5 O2 . . . 124.6(13) yes
    C2 N1 H9 . . . 109.466 no
    C2 N1 H1 . . . 109.460 no
    H9 N1 H1 . . . 109.472 no
    C2 N1 H7 . . . 109.470 no
    H9 N1 H7 . . . 109.484 no
    H1 N1 H7 . . . 109.476 no
    C5 N2 H5 . . . 119.996 no
    C5 N2 H4 . . . 120.004 no
    H5 N2 H4 . . . 120.000 no
