##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section B. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section B, and 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 is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_text
_audit_creation_method     'IUCr checking CIFGEN version 1.4'
_journal_date_recd_electronic     1994-05-16
_journal_date_accepted     1994-09-30
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     1995
_journal_volume     51
_journal_issue     2
_journal_page_first     232
_journal_page_last     240
_journal_paper_category     FA
_journal_coeditor_code     AB0328
loop_
    _publ_author_name
    'Maurin, J.K.'
    'Les, A.'
    'Winnicka-Maurin, M.'
data_ab0328a
_chemical_formula_moiety     ?
_chemical_formula_sum     'C6 H11 N O3'
_chemical_formula_weight     145.16
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
_cell_length_a     10.822(3)
_cell_length_b     13.743(2)
_cell_length_c     5.408(2)
_cell_angle_alpha     96.47(3)
_cell_angle_beta     97.97(3)
_cell_angle_gamma     86.31(2)
_cell_volume     790.0(4)
_cell_formula_units_Z     4
_exptl_crystal_density_diffrn     1.220
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     312
_exptl_absorpt_coefficient_mu     0.098
_diffrn_radiation_type     Mo
_diffrn_radiation_wavelength     0.71073
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    N1a .1453(2) .6798(2) .5135(4) .0536(6)
    O1a .1563(2) .7785(2) .5929(5) .0672(6)
    O2a .2498(2) .4576(2) .7267(4) .0726(7)
    O3a .1327(2) .49414(15) .3685(4) .0672(6)
    C1a .1983(2) .5170(2) .5904(5) .0532(7)
    C2a .2083(2) .6234(2) .6669(5) .0513(7)
    C3a .2875(3) .6580(2) .9071(5) .0548(7)
    C4a .4154(3) .6915(2) .8694(6) .0610(8)
    C5a .4845(5) .7280(4) 1.1248(9) .0988(14)
    C6a .4934(4) .6105(3) .7435(10) .0863(11)
    N1b -.1510(2) .7091(2) -.3453(5) .0552(6)
    O1b -.2229(2) .7315(2) -.5649(4) .0672(6)
    O2b .0067(2) .83069(15) .1880(4) .0660(6)
    O3b -.0108(2) .66940(14) .0609(4) .0610(6)
    C1b -.0340(2) .7636(2) .0353(5) .0511(7)
    C2b -.1143(2) .7859(2) -.1990(5) .0520(7)
    C3b -.1424(3) .8901(2) -.2500(7) .0603(8)
    C4b -.2559(5) .9321(4) -.1079(14) .066(2)
    C5b -.2596(8) 1.0436(5) -.1044(17) .107(3)
    C6b -.3755(5) .8968(5) -.2589(13) .086(2)
    C4b' -.2691(8) .9346(6) -.2167(17) .065(2)
    C5b' -.2783(12) .9469(9) .063(2)   .107(4)
    C6b' -.2941(13) 1.0323(8) -.321(2)   .120(4)
    H10a .118(5)   .811(4)   .485(9)   .123(18)
    H30a .128(4)   .4174(10) .314(7)   .094(12)
    H10b -.234(4)   .672(3)   -.640(8)   .097(13)
    H30b .047(3)   .651(3)   .226(5)   .111(14)
    H31a .242(3)   .711(2)   .991(5)   .047(7)
    H32a .295(3)   .606(2)   1.023(6)   .055(8)
    H4a .410(3)   .747(3)   .752(6)   .072(9)
    H51a .576(5)   .758(4)   1.110(10)  .136(17)
    H52a .434(5)   .781(4)   1.202(9)   .115(16)
    H53a .502(4)   .671(3)   1.243(9)   .109(14)
    H61a .507(5)   .550(4)   .854(10)   .143(18)
    H62a .52(4)   .595(3)   .579(9)   .105(15)
    H63a .578(4)   .640(3)   .716(8)   .102(12)
    H31b -.073(3)   .927(3)   -.185(7)   .077(10)
    H32b -.146(3)   .893(2)   -.427(7)   .065(9)
    H51b -.221(5)   1.028(4)   .0580(4) .109(8)
    H52b -.338(3)   1.080(4)   -.089(11)   .109(8)
    H53b -.205(4)   1.083(4)   -.173(10)  .109(8)
    H61b -.368(5)   .8264(6) -.271(10)  .109(8)
    H62b -.388(5)   .918(4)   -.424(4)   .109(8)
    H63b -.445(4)   .920(4)   -.173(9)   .109(8)
    H54b -.3663(18) .959(5)   .068(16)   .109(8)
    H55b -.235(6)   1.005(3)   .127(14)   .109(8)
    H56b -.248(6)   .895(4)   .164(13)   .109(8)
    H64b -.338(6)   1.090(3)   -.252(14)   .109(8)
    H65b -.353(6)   .984(4)   -.391(13)   .109(8)
    H66b -.250(7)   1.050(5)   -.451(11)   .109(8)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    N1a C2a 1.293(4)
    N1a O1a 1.382(3)
    O2a C1a 1.217(3)
    O3a C1a 1.323(3)
    C1a C2a 1.480(4)
    C2a C3a 1.501(4)
    C3a C4a 1.533(4)
    C4a C6a 1.510(5)
    C4a C5a 1.525(5)
    N1b C2b 1.294(4)
    N1b O1b 1.381(3)
    O2b C1b 1.226(3)
    O3b C1b 1.321(3)
    C1b C2b 1.484(4)
    C2b C3b 1.493(4)
    C3b C4b' 1.490(9)
    C3b C4b 1.581(6)
    C4b C6b 1.508(7)
    C4b C5b 1.527(7)
    C4b' C6b' 1.508(10)
    C4b' C5b' 1.517(10)
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    C2a N1a O1a 113.1(2)
    O2a C1a O3a 124.7(3)
    O2a C1a C2a 120.2(2)
    O3a C1a C2a 115.1(2)
    N1a C2a C1a 115.0(2)
    N1a C2a C3a 125.2(3)
    C1a C2a C3a 119.8(2)
    C2a C3a C4a 113.7(2)
    C6a C4a C5a 109.6(3)
    C6a C4a C3a 112.5(3)
    C5a C4a C3a 108.7(3)
    C2b N1b O1b 113.2(2)
    O2b C1b O3b 124.6(3)
    O2b C1b C2b 120.0(2)
    O3b C1b C2b 115.4(2)
    N1b C2b C1b 114.3(2)
    N1b C2b C3b 126.2(3)
    C1b C2b C3b 119.5(2)
    C4b' C3b C2b 118.2(4)
    C2b C3b C4b 108.3(3)
    C6b C4b C5b 107.5(5)
    C6b C4b C3b 108.8(5)
    C5b C4b C3b 106.8(5)
    C3b C4b' C6b' 112.8(8)
    C3b C4b' C5b' 107.3(8)
    C6b' C4b' C5b' 110.0(8)
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
    H10b O2a C1a O3a -0.6
    H10b O2a C1a C2a -178.8
    H30a O3a C1a O2a 2.3
    H30a O3a C1a C2a -179.5
    O1a N1a C2a C1a 179.4
    O1a N1a C2a C3a -1.0
    H30b N1a C2a C1a 2.1
    O2a C1a C2a N1a -177.6
    O2a C1a C2a C3a 2.8
    O3a C1a C2a N1a 4.1
    O3a C1a C2a C3a -175.5
    C2b N1b O1b H10b -177.6
    H10a O2b C1b O3b 0.6
    H10a O2b C1b C2b -178.8
    H30b O3b C1b O2b 1.7
    H30b O3b C1b C2b -178.9
    O1b N1b C2b C1b -178.4
    O1b N1b C2b C3b -0.5
    H30a N1b C2b C1b 1.0
    H30a N1b C2b C3b 178.9
    O2b C1b C2b N1b 179.9
    O2b C1b C2b C3b 1.8
    O3b C1b C2b N1b 0.4
    O3b C1b C2b C3b -177.6
data_ab0328b
_chemical_formula_moiety     ?
_chemical_formula_sum     'C5 H9 N O3'
_chemical_formula_weight     131.13
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/c 1'
_symmetry_space_group_name_Hall     '-P 2ybc'
_cell_length_a     8.568(2)
_cell_length_b     5.9160(10)
_cell_length_c     26.403(15)
_cell_angle_alpha     ?
_cell_angle_beta     92.390(10)
_cell_angle_gamma     ?
_cell_volume     1337.2(9)
_cell_formula_units_Z     8
_exptl_crystal_density_diffrn     1.303
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     0.108
_diffrn_radiation_type     Mo
_diffrn_radiation_wavelength     0.71073
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    C1a .4702(2) .2543(4) .14687(7) .0366(5)
    C2a .3709(2) .4624(4) .14327(7) .0360(5)
    C3a .3132(3) .5375(4) .19410(8) .0405(5)
    C4a .2156(2) .7466(3) .19308(7) .0347(4)
    C5a .1533(4) .8297(5) .24178(8) .0518(6)
    N1a .1884(2) .8448(3) .15060(6) .0376(4)
    O1a .0948(2) 1.0401(2) .15509(6) .0501(4)
    O2a .5067(2) .1568(2) .18603(5) .0475(4)
    O3a .5167(2) .1875(3) .10200(5) .0484(4)
    C1b .2068(2) 1.0263(3) .03225(7) .0398(5)
    C2b .2549(3) 1.0671(4) -.02088(8) .0430(5)
    C3b .1864(3) 1.2816(4) -.04374(8) .0431(5)
    C4b .2095(2) 1.3152(3) -.09920(7) .0363(5)
    C5b .1313(3) 1.5113(4) -.12454(9) .0469(9)
    N1b .2952(2) 1.1724(3) -.12153(6) .0382(4)
    O1b .3075(2) 1.2200(3) -.17362(5) .0495(4)
    O2b .1186(2) 1.1472(3) .05472(5) .0493(4)
    O3b .2693(2) .8405(3) .05223(6) .0500(4)
    H10a .088(3)   1.088(5)   .1216(10) .080(8)
    H30a .585(3)   .051(5)   .1064(10) .094(9)
    H10b .367(3)   1.109(5)   -.1821(10) .077(9)
    H30b .243(3)   .823(4)   .0860(10) .068(7)
    H21a .433(2)   .579(4)   .1291(8) .043(6)
    H22a .286(2)   .436(3)   .1193(7) .037(5)
    H31a .401(2)   .559(3)   .2169(8) .043(6)
    H32a .25(2)   .417(4)   .2088(7) .041(5)
    H51a .171(3)   .722(4)   .2663(9) .066(7)
    H52a .046(4)   .862(6)   .2368(12) .108(11)
    H53a .206(4)   .974(5)   .2522(11) .106(11)
    H21b .371(3)   1.068(4)   -.0191(7) .049(6)
    H22b .219(2)   .942(4)   -.0412(8) .052(6)
    H31b .229(3)   1.404(4)   -.0244(8) .056(7)
    H32b .072(3)   1.283(4)   -.0386(8) .056(6)
    H51b .062(4)   1.573(6)   -.1045(12) .107(11)
    H52b .077(3)   1.472(5)   -.1566(12) .103(10)
    H53b .204(4)   1.617(6)   -.1364(11) .105(11)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    C1a O2a 1.213(2)
    C1a O3a 1.326(2)
    C1a C2a 1.497(3)
    C2a C3a 1.516(3)
    C3a C4a 1.493(3)
    C4a N1a 1.276(2)
    C4a C5a 1.496(3)
    N1a O1a 1.414(2)
    C1b O2b 1.213(2)
    C1b O3b 1.323(2)
    C1b C2b 1.498(3)
    C2b C3b 1.513(3)
    C3b C4b 1.499(3)
    C4b N1b 1.279(2)
    C4b C5b 1.485(3)
    N1b O1b 1.412(2)
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    O2a C1a O3a 122.9(2)
    O2a C1a C2a 124.8(2)
    O3a C1a C2a 112.3(2)
    C1a C2a C3a 113.0(2)
    C4a C3a C2a 115.5(2)
    N1a C4a C3a 118.3(2)
    N1a C4a C5a 123.2(2)
    C3a C4a C5a 118.5(2)
    C4a N1a O1a 112.43(15)
    O2b C1b O3b 123.0(2)
    O2b C1b C2b 124.3(2)
    O3b C1b C2b 112.6(2)
    C1b C2b C3b 113.0(2)
    C4b C3b C2b 115.9(2)
    N1b C4b C5b 124.4(2)
    N1b C4b C3b 117.7(2)
    C5b C4b C3b 117.9(2)
    C4b N1b O1b 112.7(2)
    O1a H10a O2b 2.741(2)
    O1b H10b O2a 2.767(2)
    O3a H30a N1b 2.707(2)
    O3b H30b N1a 2.716(3)
