##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# 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_global
_audit_creation_method     'manual editing of form.cif'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-07-18
_journal_date_accepted     2010-08-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2328
_journal_page_last     o2328
_journal_paper_category     QO
_journal_coeditor_code     SU2200
_publ_contact_author_name     'Hai-Xiang Chen'
_publ_contact_author_address
;
    Analytical Center
    Zhejiang Sci-Tech University
    Hangzhou 310018, People's Republic of China
;
_publ_contact_author_email     cchhyy@sina.cn
_publ_contact_author_fax     '++86-571-86814835'
_publ_contact_author_phone     '++86-571-86814835'
_publ_section_title
;
Diethyl(hydroxy)ammonium 3-carboxybenzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Yun Guo'
;
    College of Pharmaceutical Sciences
    Zhejiang University of Technology
    Hangzhou 310014
    People's Republic of China
;
    'Cong Wang'
;
    College of Pharmaceutical Sciences
    Zhejiang University of Technology
    Hangzhou 310014
    People's Republic of China
;
    'Hai-Xiang Chen'
;
    Analytical Center
    Zhejiang Sci-Tech University
    Hangzhou 310018, People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Diethyl(hydroxy)ammonium 3-carboxybenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H12 N O +, C8 H5 O4 -'
_chemical_formula_sum     'C12 H17 N O5'
_chemical_formula_iupac     'C4 H12 N O +, C8 H5 O4 -'
_chemical_formula_weight     255.27
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.535(7)
_cell_length_b     11.937(9)
_cell_length_c     11.660(9)
_cell_angle_alpha     90.00
_cell_angle_beta     96.959(15)
_cell_angle_gamma     90.00
_cell_volume     1317.4(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3574
_cell_measurement_theta_min     2.12
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.287
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     544
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.967
_exptl_absorpt_correction_T_max     0.977
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(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     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6749
_diffrn_reflns_av_R_equivalents     0.0285
_diffrn_reflns_av_sigmaI/netI     0.0346
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     2317
_reflns_number_gt     1912
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0922
_refine_ls_R_factor_gt     0.0751
_refine_ls_wR_factor_gt     0.1914
_refine_ls_wR_factor_ref     0.2028
_refine_ls_goodness_of_fit_ref     1.187
_refine_ls_restrained_S_all     1.187
_refine_ls_number_reflns     2317
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0962P)²+0.4181P] 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     0.203
_refine_diff_density_min     -0.256
_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     'SMART (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2007)'
_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
    O O2 0.8613(3) 0.64114(19) -0.0032(2) 0.0693(8) Uani d . 1 . .
    O O3 0.4161(3) 0.39290(18) 0.2751(2) 0.0755(9) Uani d . 1 . .
    O O4 0.4378(2) 0.22073(16) 0.2114(2) 0.0594(7) Uani d . 1 . .
    H H4 0.3865 0.2064 0.2611 0.089 Uiso calc R 1 . .
    C C1 0.7731(3) 0.6172(2) 0.0625(3) 0.0418(7) Uani d . 1 . .
    C C2 0.7101(3) 0.5018(2) 0.0565(2) 0.0358(7) Uani d . 1 . .
    C C3 0.6177(3) 0.4682(2) 0.1322(2) 0.0363(7) Uani d . 1 . .
    H H3 0.5928 0.5181 0.1876 0.044 Uiso calc R 1 . .
    C C4 0.5616(3) 0.3611(2) 0.1267(2) 0.0364(7) Uani d . 1 . .
    C C5 0.5951(3) 0.2889(2) 0.0422(3) 0.0481(8) Uani d . 1 . .
    H H5A 0.5568 0.2172 0.0373 0.058 Uiso calc R 1 . .
    C C6 0.6849(4) 0.3223(3) -0.0350(3) 0.0555(9) Uani d . 1 . .
    H H6 0.7061 0.2734 -0.0926 0.067 Uiso calc R 1 . .
    C C7 0.7434(3) 0.4276(2) -0.0276(3) 0.0483(8) Uani d . 1 . .
    H H7 0.8056 0.4492 -0.0791 0.058 Uiso calc R 1 . .
    C C8 0.4642(3) 0.3282(2) 0.2117(3) 0.0429(7) Uani d . 1 . .
    O O1 0.7347(2) 0.68498(17) 0.13536(19) 0.0534(6) Uani d . 1 . .
    O O5 0.9635(3) 0.83592(18) 0.0383(2) 0.0613(7) Uani d . 1 . .
    H H5 0.9340 0.7740 0.0166 0.092 Uiso calc R 1 . .
    N N1 0.8850(3) 0.8758(2) 0.1251(2) 0.0504(7) Uani d . 1 . .
    H H1 0.8150 0.8258 0.1335 0.060 Uiso calc R 1 . .
    C C9 1.0396(4) 0.7722(4) 0.2759(4) 0.0870(13) Uani d . 1 . .
    H H9A 0.9648 0.7224 0.2905 0.130 Uiso calc R 1 . .
    H H9B 1.1032 0.7821 0.3456 0.130 Uiso calc R 1 . .
    H H9C 1.0900 0.7410 0.2170 0.130 Uiso calc R 1 . .
    C C10 0.9787(4) 0.8832(3) 0.2364(3) 0.0697(11) Uani d . 1 . .
    H H10A 0.9251 0.9130 0.2951 0.084 Uiso calc R 1 . .
    H H10B 1.0551 0.9349 0.2277 0.084 Uiso calc R 1 . .
    C C11 0.7195(5) 0.9731(4) -0.0227(4) 0.0870(13) Uani d . 1 . .
    H H11A 0.7696 0.9443 -0.0830 0.131 Uiso calc R 1 . .
    H H11B 0.6806 1.0452 -0.0450 0.131 Uiso calc R 1 . .
    H H11C 0.6446 0.9226 -0.0101 0.131 Uiso calc R 1 . .
    C C12 0.8190(4) 0.9843(3) 0.0861(3) 0.0635(10) Uani d . 1 . .
    H H12A 0.8927 1.0374 0.0735 0.076 Uiso calc R 1 . .
    H H12B 0.7680 1.0141 0.1465 0.076 Uiso calc R 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
    O2 0.0955(18) 0.0479(14) 0.0763(17) -0.0257(12) 0.0577(15) -0.0171(12)
    O3 0.106(2) 0.0381(13) 0.097(2) -0.0105(12) 0.0701(17) -0.0130(12)
    O4 0.0767(17) 0.0336(12) 0.0770(18) -0.0074(10) 0.0459(13) -0.0033(10)
    C1 0.0488(17) 0.0335(16) 0.0462(17) 0.0001(13) 0.0186(14) -0.0018(13)
    C2 0.0364(14) 0.0309(15) 0.0406(16) 0.0006(11) 0.0072(12) 0.0016(12)
    C3 0.0409(15) 0.0283(15) 0.0414(16) 0.0034(11) 0.0123(12) -0.0022(12)
    C4 0.0360(14) 0.0310(15) 0.0432(16) 0.0028(11) 0.0085(12) 0.0016(12)
    C5 0.0527(18) 0.0322(16) 0.063(2) -0.0059(13) 0.0199(15) -0.0078(14)
    C6 0.072(2) 0.0399(18) 0.061(2) -0.0105(15) 0.0341(17) -0.0197(15)
    C7 0.0584(19) 0.0402(17) 0.0521(19) -0.0041(14) 0.0293(15) -0.0060(14)
    C8 0.0490(17) 0.0308(16) 0.0515(18) -0.0005(13) 0.0168(14) -0.0026(13)
    O1 0.0594(13) 0.0350(12) 0.0728(15) -0.0094(10) 0.0364(12) -0.0134(10)
    O5 0.0832(17) 0.0478(14) 0.0618(15) -0.0209(12) 0.0448(13) -0.0137(11)
    N1 0.0623(17) 0.0404(15) 0.0540(16) -0.0215(12) 0.0296(13) -0.0096(12)
    C9 0.077(3) 0.115(4) 0.069(3) 0.006(3) 0.011(2) 0.003(3)
    C10 0.077(3) 0.079(3) 0.055(2) -0.024(2) 0.0163(19) -0.0136(19)
    C11 0.099(3) 0.068(3) 0.093(3) -0.009(2) 0.007(3) 0.007(2)
    C12 0.083(2) 0.0390(19) 0.075(2) -0.0208(17) 0.035(2) -0.0081(16)
_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
    O2 C1 . 1.238(3) yes
    O3 C8 . 1.198(3) ?
    O4 C8 . 1.307(4) ?
    O4 H4 . 0.8200 ?
    C1 O1 . 1.259(3) yes
    C1 C2 . 1.502(4) ?
    C2 C3 . 1.380(4) ?
    C2 C7 . 1.386(4) ?
    C3 C4 . 1.384(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.375(4) ?
    C4 C8 . 1.491(4) ?
    C5 C6 . 1.374(4) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.374(4) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    O5 N1 . 1.412(3) ?
    O5 H5 . 0.8200 ?
    N1 C10 . 1.486(5) ?
    N1 C12 . 1.487(5) ?
    N1 H1 . 0.9100 ?
    C9 C10 . 1.496(6) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.495(6) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
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
    C8 O4 H4 . . 109.5 ?
    O2 C1 O1 . . 123.0(3) ?
    O2 C1 C2 . . 118.7(2) ?
    O1 C1 C2 . . 118.3(2) ?
    C3 C2 C7 . . 119.1(3) ?
    C3 C2 C1 . . 121.3(2) ?
    C7 C2 C1 . . 119.6(2) ?
    C2 C3 C4 . . 120.8(3) ?
    C2 C3 H3 . . 119.6 ?
    C4 C3 H3 . . 119.6 ?
    C5 C4 C3 . . 119.3(3) ?
    C5 C4 C8 . . 121.9(3) ?
    C3 C4 C8 . . 118.8(2) ?
    C6 C5 C4 . . 120.3(3) ?
    C6 C5 H5A . . 119.8 ?
    C4 C5 H5A . . 119.8 ?
    C7 C6 C5 . . 120.3(3) ?
    C7 C6 H6 . . 119.8 ?
    C5 C6 H6 . . 119.8 ?
    C6 C7 C2 . . 120.2(3) ?
    C6 C7 H7 . . 119.9 ?
    C2 C7 H7 . . 119.9 ?
    O3 C8 O4 . . 123.1(3) ?
    O3 C8 C4 . . 123.8(3) ?
    O4 C8 C4 . . 113.1(2) ?
    N1 O5 H5 . . 109.5 ?
    O5 N1 C10 . . 109.4(3) ?
    O5 N1 C12 . . 108.4(2) ?
    C10 N1 C12 . . 113.8(3) ?
    O5 N1 H1 . . 108.4 ?
    C10 N1 H1 . . 108.4 ?
    C12 N1 H1 . . 108.4 ?
    C10 C9 H9A . . 109.5 ?
    C10 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C10 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N1 C10 C9 . . 112.7(3) ?
    N1 C10 H10A . . 109.0 ?
    C9 C10 H10A . . 109.0 ?
    N1 C10 H10B . . 109.0 ?
    C9 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    C12 C11 H11A . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C12 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N1 C12 C11 . . 112.5(3) ?
    N1 C12 H12A . . 109.1 ?
    C11 C12 H12A . . 109.1 ?
    N1 C12 H12B . . 109.1 ?
    C11 C12 H12B . . 109.1 ?
    H12A C12 H12B . . 107.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2 C1 C2 C3 . . . . 176.0(3) ?
    O1 C1 C2 C3 . . . . -3.1(4) ?
    O2 C1 C2 C7 . . . . -4.8(4) ?
    O1 C1 C2 C7 . . . . 176.0(3) ?
    C7 C2 C3 C4 . . . . 1.6(4) ?
    C1 C2 C3 C4 . . . . -179.2(3) ?
    C2 C3 C4 C5 . . . . -2.1(4) ?
    C2 C3 C4 C8 . . . . 178.9(2) ?
    C3 C4 C5 C6 . . . . 0.9(4) ?
    C8 C4 C5 C6 . . . . 179.8(3) ?
    C4 C5 C6 C7 . . . . 0.8(5) ?
    C5 C6 C7 C2 . . . . -1.3(5) ?
    C3 C2 C7 C6 . . . . 0.1(5) ?
    C1 C2 C7 C6 . . . . -179.1(3) ?
    C5 C4 C8 O3 . . . . -168.5(3) ?
    C3 C4 C8 O3 . . . . 10.4(4) ?
    C5 C4 C8 O4 . . . . 12.4(4) ?
    C3 C4 C8 O4 . . . . -168.7(3) ?
    O5 N1 C10 C9 . . . . -60.7(4) ?
    C12 N1 C10 C9 . . . . 177.9(3) ?
    O5 N1 C12 C11 . . . . 61.2(4) ?
    C10 N1 C12 C11 . . . . -176.9(3) ?
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
    _geom_hbond_publ_flag
    N1 H1 O1 . 0.91 1.85 2.702(4) 155 yes
    O5 H5 O2 . 0.82 1.74 2.545(4) 169 yes
    O4 H4 O1 2_645 0.82 1.79 2.606(4) 175 yes
    C10 H10A O2 4_576 0.97 2.58 3.373(5) 139 yes
    C12 H12A O5 3_775 0.97 2.51 3.426(5) 157 yes
    C12 H12B O3 2_655 0.97 2.53 3.117(5) 119 yes
