##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-[1-(2-Hydroxypropyliminio)ethyl]-5-methoxyphenolate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H17 N O3'
_chemical_formula_sum     'C12 H17 N O3'
_chemical_formula_iupac     'C12 H17 N O3'
_chemical_formula_weight     223.27
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.714(2)
_cell_length_b     9.672(4)
_cell_length_c     10.869(3)
_cell_angle_alpha     98.19(2)
_cell_angle_beta     96.71(2)
_cell_angle_gamma     93.35(3)
_cell_volume     588.8(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     35
_cell_measurement_theta_min     3.07
_cell_measurement_theta_max     12.44
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.54
_exptl_crystal_size_mid     0.46
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.259
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     240
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens P4'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2506
_diffrn_reflns_av_R_equivalents     0.0172
_diffrn_reflns_av_sigmaI/netI     0.0551
_diffrn_reflns_theta_min     1.91
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     3.91
_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 > 2sigma(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     2187
_reflns_number_gt     1070
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0889
_refine_ls_R_factor_gt     0.0412
_refine_ls_wR_factor_gt     0.0754
_refine_ls_wR_factor_ref     0.0814
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.986
_refine_ls_number_reflns     2187
_refine_ls_number_parameters     155
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0268P)²] 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     0.153
_refine_diff_density_min     -0.150
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.013(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'XSCANS (Siemens, 1994)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'SHELXTL (Siemens, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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
    O O1 0.1251(2) 0.16218(15) 0.37940(13) 0.0595(4) Uani d . 1 . .
    O O2 0.2213(3) 0.37187(15) 0.01565(13) 0.0661(5) Uani d . 1 . .
    O O3 0.1269(3) 0.08674(17) 0.69327(15) 0.0600(4) Uani d D 1 . .
    N N 0.4475(3) 0.21279(18) 0.56303(15) 0.0474(5) Uani d D 1 . .
    C C1 0.2480(4) 0.2422(2) 0.32170(18) 0.0446(5) Uani d . 1 . .
    C C2 0.1621(4) 0.2657(2) 0.19827(18) 0.0495(6) Uani d . 1 . .
    H H2 0.0150 0.2246 0.1609 0.059 Uiso calc R 1 . .
    C C3 0.2899(4) 0.3465(2) 0.13438(19) 0.0486(6) Uani d . 1 . .
    C C4 0.5101(4) 0.4122(2) 0.18852(19) 0.0526(6) Uani d . 1 . .
    H H4 0.5966 0.4681 0.1443 0.063 Uiso calc R 1 . .
    C C5 0.5961(4) 0.3935(2) 0.30633(19) 0.0506(6) Uani d . 1 . .
    H H5 0.7426 0.4375 0.3413 0.061 Uiso calc R 1 . .
    C C6 0.4737(3) 0.31045(19) 0.37786(18) 0.0403(5) Uani d . 1 . .
    C C7 0.5699(3) 0.2916(2) 0.50153(18) 0.0415(5) Uani d . 1 . .
    C C8 0.8039(3) 0.3596(2) 0.56320(18) 0.0543(6) Uani d . 1 . .
    H H8A 0.8356 0.3343 0.6454 0.065 Uiso calc PR 0.50 . .
    H H8B 0.8010 0.4595 0.5697 0.065 Uiso calc PR 0.50 . .
    H H8C 0.9254 0.3288 0.5141 0.065 Uiso calc PR 0.50 . .
    H H8D 0.8724 0.4141 0.5074 0.065 Uiso calc PR 0.50 . .
    H H8E 0.9070 0.2889 0.5831 0.065 Uiso calc PR 0.50 . .
    H H8F 0.7826 0.4196 0.6388 0.065 Uiso calc PR 0.50 . .
    C C9 0.5161(4) 0.1842(2) 0.69031(18) 0.0523(6) Uani d . 1 . .
    H H9A 0.4939 0.2651 0.7504 0.063 Uiso calc R 1 . .
    H H9B 0.6819 0.1661 0.7009 0.063 Uiso calc R 1 . .
    C C10 0.3682(4) 0.0592(2) 0.71358(19) 0.0527(6) Uani d . 1 . .
    H H10 0.3956 -0.0223 0.6538 0.063 Uiso calc R 1 . .
    C C11 0.4376(4) 0.0290(2) 0.84557(19) 0.0698(7) Uani d . 1 . .
    H H11A 0.4123 0.1086 0.9048 0.084 Uiso calc R 1 . .
    H H11B 0.6014 0.0106 0.8560 0.084 Uiso calc R 1 . .
    H H11C 0.3429 -0.0513 0.8594 0.084 Uiso calc R 1 . .
    C C12 -0.0019(4) 0.3077(3) -0.0468(2) 0.0782(8) Uani d . 1 . .
    H H12A -0.0003 0.2077 -0.0542 0.094 Uiso calc R 1 . .
    H H12B -0.0290 0.3342 -0.1289 0.094 Uiso calc R 1 . .
    H H12C -0.1257 0.3384 0.0007 0.094 Uiso calc R 1 . .
    H H3O 0.052(5) 0.0089(17) 0.672(3) 0.142(14) Uiso d D 1 . .
    H H0N 0.315(3) 0.176(3) 0.520(3) 0.170 Uiso d 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
    O1 0.0500(10) 0.0712(10) 0.0547(10) -0.0145(8) -0.0006(8) 0.0148(8)
    O2 0.0760(12) 0.0763(11) 0.0453(9) 0.0046(9) -0.0014(9) 0.0149(8)
    O3 0.0487(10) 0.0584(11) 0.0724(11) 0.0011(9) 0.0045(8) 0.0124(9)
    N 0.0436(12) 0.0533(12) 0.0437(11) -0.0019(10) -0.0001(9) 0.0088(9)
    C1 0.0421(14) 0.0441(13) 0.0459(14) 0.0013(11) 0.0061(11) 0.0013(11)
    C2 0.0439(14) 0.0549(14) 0.0471(13) 0.0007(11) -0.0004(11) 0.0048(11)
    C3 0.0534(15) 0.0515(14) 0.0409(13) 0.0096(12) 0.0047(11) 0.0053(11)
    C4 0.0518(15) 0.0564(15) 0.0515(14) -0.0016(12) 0.0110(12) 0.0128(11)
    C5 0.0417(13) 0.0548(14) 0.0536(14) -0.0025(11) 0.0052(11) 0.0061(11)
    C6 0.0377(13) 0.0378(12) 0.0438(12) -0.0020(10) 0.0057(10) 0.0025(10)
    C7 0.0367(12) 0.0394(12) 0.0471(13) 0.0010(10) 0.0060(11) 0.0021(10)
    C8 0.0425(13) 0.0637(15) 0.0550(14) -0.0051(11) 0.0014(11) 0.0105(11)
    C9 0.0493(14) 0.0592(15) 0.0468(14) -0.0030(12) -0.0012(11) 0.0111(11)
    C10 0.0528(15) 0.0505(14) 0.0528(14) 0.0037(12) 0.0013(11) 0.0062(11)
    C11 0.0779(18) 0.0716(17) 0.0617(16) 0.0029(14) 0.0015(13) 0.0231(13)
    C12 0.0779(19) 0.100(2) 0.0516(15) 0.0149(16) -0.0089(14) 0.0053(14)
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.290(2) y
    O2 C3 . 1.365(2) y
    O2 C12 . 1.434(2) y
    O3 C10 . 1.417(2) y
    O3 H3O . 0.833(10) ?
    N C7 . 1.307(2) y
    N C9 . 1.463(2) y
    N H0N . 0.869(10) ?
    C1 C2 . 1.428(2) y
    C1 C6 . 1.440(2) y
    C2 C3 . 1.354(3) y
    C2 H2 . 0.9300 ?
    C3 C4 . 1.400(3) y
    C4 C5 . 1.358(2) y
    C4 H4 . 0.9300 ?
    C5 C6 . 1.406(3) y
    C5 H5 . 0.9300 ?
    C6 C7 . 1.432(2) y
    C7 C8 . 1.494(2) y
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C8 H8D . 0.9600 ?
    C8 H8E . 0.9600 ?
    C8 H8F . 0.9600 ?
    C9 C10 . 1.503(3) y
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.517(3) y
    C10 H10 . 0.9800 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
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
    C3 O2 C12 . . 117.86(17) ?
    C10 O3 H3O . . 106(2) ?
    C7 N C9 . . 126.09(17) ?
    C7 N H0N . . 113(2) ?
    C9 N H0N . . 121(2) ?
    O1 C1 C2 . . 120.25(19) ?
    O1 C1 C6 . . 122.02(19) ?
    C2 C1 C6 . . 117.73(19) ?
    C3 C2 C1 . . 121.5(2) ?
    C3 C2 H2 . . 119.2 ?
    C1 C2 H2 . . 119.2 ?
    C2 C3 O2 . . 124.8(2) ?
    C2 C3 C4 . . 120.8(2) ?
    O2 C3 C4 . . 114.3(2) ?
    C5 C4 C3 . . 119.2(2) ?
    C5 C4 H4 . . 120.4 ?
    C3 C4 H4 . . 120.4 ?
    C4 C5 C6 . . 123.0(2) ?
    C4 C5 H5 . . 118.5 ?
    C6 C5 H5 . . 118.5 ?
    C5 C6 C7 . . 121.74(19) ?
    C5 C6 C1 . . 117.67(19) ?
    C7 C6 C1 . . 120.59(18) ?
    N C7 C6 . . 118.74(18) ?
    N C7 C8 . . 118.83(18) ?
    C6 C7 C8 . . 122.44(18) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C7 C8 H8D . . 109.5 ?
    H8A C8 H8D . . 141.1 ?
    H8B C8 H8D . . 56.3 ?
    H8C C8 H8D . . 56.3 ?
    C7 C8 H8E . . 109.5 ?
    H8A C8 H8E . . 56.3 ?
    H8B C8 H8E . . 141.1 ?
    H8C C8 H8E . . 56.3 ?
    H8D C8 H8E . . 109.5 ?
    C7 C8 H8F . . 109.5 ?
    H8A C8 H8F . . 56.3 ?
    H8B C8 H8F . . 56.3 ?
    H8C C8 H8F . . 141.1 ?
    H8D C8 H8F . . 109.5 ?
    H8E C8 H8F . . 109.5 ?
    N C9 C10 . . 109.68(16) ?
    N C9 H9A . . 109.7 ?
    C10 C9 H9A . . 109.7 ?
    N C9 H9B . . 109.7 ?
    C10 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    O3 C10 C9 . . 108.45(18) ?
    O3 C10 C11 . . 111.66(18) ?
    C9 C10 C11 . . 110.06(17) ?
    O3 C10 H10 . . 108.9 ?
    C9 C10 H10 . . 108.9 ?
    C11 C10 H10 . . 108.9 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    O2 C12 H12A . . 109.5 ?
    O2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    O2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . -178.43(19) ?
    C6 C1 C2 C3 . . . . 1.6(3) ?
    C1 C2 C3 O2 . . . . 178.90(18) ?
    C1 C2 C3 C4 . . . . -1.2(3) ?
    C12 O2 C3 C2 . . . . -0.4(3) ?
    C12 O2 C3 C4 . . . . 179.66(18) ?
    C2 C3 C4 C5 . . . . 0.4(3) ?
    O2 C3 C4 C5 . . . . -179.66(19) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . 179.4(2) ?
    C4 C5 C6 C1 . . . . 0.5(3) ?
    O1 C1 C6 C5 . . . . 178.81(19) ?
    C2 C1 C6 C5 . . . . -1.2(3) ?
    O1 C1 C6 C7 . . . . -0.2(3) ?
    C2 C1 C6 C7 . . . . 179.85(19) ?
    C9 N C7 C6 . . . . -178.84(18) ?
    C9 N C7 C8 . . . . 0.7(3) ?
    C5 C6 C7 N . . . . -179.82(19) ?
    C1 C6 C7 N . . . . -0.9(3) ?
    C5 C6 C7 C8 . . . . 0.7(3) ?
    C1 C6 C7 C8 . . . . 179.64(18) ?
    C7 N C9 C10 . . . . -163.7(2) ?
    N C9 C10 O3 . . . . -57.4(2) ?
    N C9 C10 C11 . . . . -179.81(18) ?
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
    O3 H3O O1 2_556 0.830(10)
                            1.87(2) 2.698(2) 178(3)
    N H0N O1 . 0.870(10)
                       1.75(2) 2.525(2) 147(3)
data_global
_journal_date_recd_electronic     2006-09-20
_journal_date_accepted     2006-11-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     12
_journal_page_first     o5916
_journal_page_last     o5917
_journal_paper_category     EO
_journal_coeditor_code     WW2054
_publ_contact_author_name     'Zhenming, Zhang'
_publ_contact_author_address
;
  Department of Chemical Engineering
  Huaihai Institute of Technology
  Lianyungang 222005
  P.R.China
;
_publ_contact_author_email     lyghhit@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86 518 5817483'
_publ_section_title
;
2-[1-(2-Hydroxypropyliminio)ethyl]-5-methoxyphenolate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhang, Zhen-Ming'
;
  Department of Chemical Engineering
  Huaihai Institute of Technology
  Lianyungang 222005
  People's Republic of China
;
    'Li, Shu-An'
;
  Department of Chemical Engineering
  Huaihai Institute of Technology
  Lianyungang 222005
  People's Republic of China
;
