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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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. 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/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(3-Oxocyclohex-1-enylamino)acetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H11 N O3'
_chemical_formula_sum     'C8 H11 N O3'
_chemical_formula_iupac     'C8 H11 N O3'
_chemical_formula_weight     169.18
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     5.1380(10)
_cell_length_b     12.983(3)
_cell_length_c     12.345(3)
_cell_angle_alpha     90.00
_cell_angle_beta     92.89(3)
_cell_angle_gamma     90.00
_cell_volume     822.4(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6177
_cell_measurement_theta_min     3.14
_cell_measurement_theta_max     27.52
_cell_measurement_temperature     291(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.9640
_exptl_absorpt_correction_T_max     0.9767
_exptl_special_details
;
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7743
_diffrn_reflns_av_R_equivalents     0.0322
_diffrn_reflns_av_sigmaI/netI     0.0346
_diffrn_reflns_theta_min     3.14
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1854
_reflns_number_gt     1461
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0510
_refine_ls_R_factor_gt     0.0412
_refine_ls_wR_factor_gt     0.1132
_refine_ls_wR_factor_ref     0.1173
_refine_ls_goodness_of_fit_ref     1.128
_refine_ls_restrained_S_all     1.128
_refine_ls_number_reflns     1854
_refine_ls_number_parameters     127
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0593P)²+0.1182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.183
_refine_diff_density_min     -0.186
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C5' -0.308(3) 1.0310(8) 0.2164(12) 0.043(4) Uani d PU 0.135(6) A 2
    H H5'1 -0.4453 1.0472 0.2648 0.052 Uiso calc PR 0.135(6) A 2
    H H5'2 -0.2880 1.0900 0.1693 0.052 Uiso calc PR 0.135(6) A 2
    C C5 -0.1653(5) 1.01745(14) 0.16773(17) 0.0444(7) Uani d P 0.865(6) A 1
    H H5A -0.0283 0.9987 0.1202 0.053 Uiso calc PR 0.865(6) A 1
    H H5B -0.2226 1.0867 0.1489 0.053 Uiso calc PR 0.865(6) A 1
    C C1 0.0056(2) 0.90870(10) 0.31865(10) 0.0301(3) Uani d . 1 A .
    C C2 -0.1357(3) 0.82688(10) 0.27717(11) 0.0331(3) Uani d . 1 . .
    H H2A -0.0941 0.7608 0.3015 0.040 Uiso calc R 1 . .
    C C3 -0.3418(3) 0.83987(10) 0.19878(10) 0.0323(3) Uani d . 1 A .
    C C4 -0.3913(3) 0.94381(12) 0.15005(13) 0.0439(4) Uani d . 1 . .
    H H4A -0.5440 0.9734 0.1811 0.053 Uiso calc R 1 A 1
    H H4B -0.4292 0.9360 0.0727 0.053 Uiso calc R 1 A 1
    C C6 -0.0589(3) 1.01603(11) 0.28306(13) 0.0445(4) Uani d . 1 . .
    H H6A 0.0968 1.0583 0.2897 0.053 Uiso calc R 1 A 1
    H H6B -0.1866 1.0450 0.3297 0.053 Uiso calc R 1 A 1
    C C7 0.2932(3) 0.79797(11) 0.43069(11) 0.0348(3) Uani d . 1 A .
    H H7A 0.3407 0.7560 0.3698 0.042 Uiso calc R 1 . .
    H H7B 0.1534 0.7633 0.4661 0.042 Uiso calc R 1 . .
    C C8 0.5245(3) 0.80897(10) 0.50935(10) 0.0324(3) Uani d . 1 . .
    H H1 0.274(3) 0.9517(10) 0.4179(13) 0.053(5) Uiso d D 1 . .
    H H2 0.762(3) 0.7271(19) 0.5786(16) 0.089(8) Uiso d D 1 . .
    N N1 0.2035(2) 0.89704(9) 0.39184(9) 0.0350(3) Uani d D 1 . .
    O O1 0.5998(2) 0.89070(8) 0.54410(10) 0.0549(4) Uani d . 1 . .
    O O2 0.6287(2) 0.72005(8) 0.53416(8) 0.0425(3) Uani d D 1 . .
    O O3 -0.4844(2) 0.76566(8) 0.16931(9) 0.0468(3) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C5' 0.044(7) 0.025(5) 0.059(7) 0.005(4) -0.011(5) 0.004(4)
    C5 0.0481(13) 0.0335(9) 0.0494(12) -0.0016(8) -0.0183(10) 0.0112(7)
    C1 0.0275(6) 0.0328(7) 0.0291(6) 0.0012(5) -0.0077(5) -0.0014(5)
    C2 0.0330(7) 0.0294(7) 0.0353(7) -0.0022(5) -0.0134(5) 0.0034(5)
    C3 0.0288(6) 0.0369(7) 0.0302(6) -0.0024(5) -0.0083(5) -0.0024(5)
    C4 0.0399(8) 0.0430(8) 0.0464(8) 0.0020(6) -0.0205(6) 0.0053(6)
    C6 0.0435(8) 0.0295(7) 0.0579(9) 0.0025(6) -0.0221(7) -0.0043(6)
    C7 0.0318(7) 0.0362(7) 0.0350(7) -0.0053(5) -0.0132(6) 0.0044(5)
    C8 0.0305(6) 0.0356(7) 0.0300(6) -0.0006(5) -0.0093(5) 0.0010(5)
    N1 0.0328(6) 0.0323(6) 0.0379(6) -0.0032(5) -0.0172(5) -0.0015(4)
    O1 0.0560(7) 0.0383(6) 0.0662(7) 0.0015(5) -0.0378(6) -0.0078(5)
    O2 0.0438(6) 0.0385(6) 0.0431(6) 0.0038(4) -0.0195(5) 0.0021(4)
    O3 0.0441(6) 0.0423(6) 0.0510(6) -0.0104(4) -0.0254(5) -0.0008(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C5' C4 . 1.448(12) ?
    C5' C6 . 1.500(12) ?
    C5' H5'1 . 0.9700 ?
    C5' H5'2 . 0.9700 ?
    C5 C6 . 1.499(2) ?
    C5 C4 . 1.511(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C1 N1 . 1.3344(17) ?
    C1 C2 . 1.3710(18) ?
    C1 C6 . 1.4931(19) ?
    C2 C3 . 1.4082(18) ?
    C2 H2A . 0.9300 ?
    C3 O3 . 1.2533(16) ?
    C3 C4 . 1.494(2) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 N1 . 1.4403(17) ?
    C7 C8 . 1.5030(18) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 O1 . 1.2013(17) ?
    C8 O2 . 1.3025(17) ?
    N1 H1 . 0.853(9) ?
    O2 H2 . 0.862(10) ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    C4 C5' C6 . . 115.4(8) ?
    C4 C5' H5'1 . . 108.4 ?
    C6 C5' H5'1 . . 108.4 ?
    C4 C5' H5'2 . . 108.4 ?
    C6 C5' H5'2 . . 108.4 ?
    H5'1 C5' H5'2 . . 107.5 ?
    C6 C5 C4 . . 111.72(16) ?
    C6 C5 H5A . . 109.3 ?
    C4 C5 H5A . . 109.3 ?
    C6 C5 H5B . . 109.3 ?
    C4 C5 H5B . . 109.3 ?
    H5A C5 H5B . . 107.9 ?
    N1 C1 C2 . . 122.41(12) ?
    N1 C1 C6 . . 117.07(12) ?
    C2 C1 C6 . . 120.52(12) ?
    C1 C2 C3 . . 121.96(12) ?
    C1 C2 H2A . . 119.0 ?
    C3 C2 H2A . . 119.0 ?
    O3 C3 C2 . . 121.05(13) ?
    O3 C3 C4 . . 119.49(12) ?
    C2 C3 C4 . . 119.46(12) ?
    C5' C4 C3 . . 116.0(5) ?
    C5' C4 C5 . . 38.9(6) ?
    C3 C4 C5 . . 113.54(12) ?
    C5' C4 H4A . . 71.8 ?
    C3 C4 H4A . . 108.9 ?
    C5 C4 H4A . . 108.9 ?
    C5' C4 H4B . . 132.6 ?
    C3 C4 H4B . . 108.9 ?
    C5 C4 H4B . . 108.9 ?
    H4A C4 H4B . . 107.7 ?
    C1 C6 C5 . . 110.84(13) ?
    C1 C6 C5' . . 116.9(4) ?
    C5 C6 C5' . . 38.4(6) ?
    C1 C6 H6A . . 109.5 ?
    C5 C6 H6A . . 109.5 ?
    C5' C6 H6A . . 130.6 ?
    C1 C6 H6B . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    C5' C6 H6B . . 72.0 ?
    H6A C6 H6B . . 108.1 ?
    N1 C7 C8 . . 111.08(11) ?
    N1 C7 H7A . . 109.4 ?
    C8 C7 H7A . . 109.4 ?
    N1 C7 H7B . . 109.4 ?
    C8 C7 H7B . . 109.4 ?
    H7A C7 H7B . . 108.0 ?
    O1 C8 O2 . . 125.30(13) ?
    O1 C8 C7 . . 122.99(12) ?
    O2 C8 C7 . . 111.71(11) ?
    C1 N1 C7 . . 123.16(11) ?
    C1 N1 H1 . . 117.2(13) ?
    C7 N1 H1 . . 119.6(13) ?
    C8 O2 H2 . . 111.1(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 O1 3_676 0.853(9) 2.190(10) 3.0266(17) 166.9(17)
    O2 H2 O3 4_776 0.862(10) 1.676(10) 2.5369(16) 176(2)
data_global
_journal_date_recd_electronic     2009-09-23
_journal_date_accepted     2009-09-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2776
_journal_page_last     o2776
_journal_paper_category     QO
_journal_coeditor_code     NG2648
_publ_contact_author_name     'Prof. Lin Xu'
_publ_contact_author_address
;
Key Laboratory of Polyoxometalate Science of Ministry of Education
Northeast Normal University
Changchun 130024
People's Republic of China
;
_publ_contact_author_email     liul515@nenu.edu.cn
_publ_contact_author_fax     '(86)431 8526 9668'
_publ_contact_author_phone     '(86)431 8526 9668'
_publ_section_title
;
2-(3-Oxocyclohex-1-enylamino)acetic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Liu, Li' .
;
Key Laboratory of Polyoxometalate Science of the Ministry of Education
Northeast Normal University
Changchun 130024
People's Republic of China
;
    'Liu, Li-Zhen' .
;
Key Laboratory of Polyoxometalate Science of the Ministry of Education
Northeast Normal University
Changchun 130024
People's Republic of China
;
    'Liu, Xi-Zheng' .
;
Key Laboratory of Polyoxometalate Science of the Ministry of Education
Northeast Normal University
Changchun 130024
People's Republic of China
;
    'Bi, Bo' .
;
Key Laboratory of Polyoxometalate Science of the Ministry of Education
Northeast Normal University
Changchun 130024
People's Republic of China
;
    'Xu, Lin' .
;
Key Laboratory of Polyoxometalate Science of the Ministry of Education
Northeast Normal University
Changchun 130024
People's Republic of China
;
