##############################################################################
###                                                                        ###
###        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                                                              #
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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-Methyl-1,2,3,4-tetrahydrocarbolin-2-ium-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H14 N2 O2'
_chemical_formula_sum     'C13 H14 N2 O2'
_chemical_formula_iupac     'C13 H14 N2 O2'
_chemical_formula_weight     230.26
_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, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.9772(8)
_cell_length_b     14.520(2)
_cell_length_c     15.307(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1106.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     666
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     18.04
_cell_measurement_temperature     296(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     488
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.9705
_exptl_absorpt_correction_T_max     0.9876
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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 APEXII CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5528
_diffrn_reflns_av_R_equivalents     0.0530
_diffrn_reflns_av_sigmaI/netI     0.0572
_diffrn_reflns_theta_min     1.93
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     5536
_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     1166
_reflns_number_gt     880
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0578
_refine_ls_R_factor_gt     0.0418
_refine_ls_wR_factor_gt     0.1080
_refine_ls_wR_factor_ref     0.1173
_refine_ls_goodness_of_fit_ref     1.001
_refine_ls_restrained_S_all     1.001
_refine_ls_number_reflns     1166
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0740P)²+0.0000P] 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     0.222
_refine_diff_density_min     -0.173
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.026(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;ORTEPIII (Burnett & Johnson, 1996) and
ORTEP-3 for Windows (Farrugia, 1997)
;
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    N N1 0.3184(7) 0.56276(18) 0.71317(15) 0.0402(7) Uani d . 1 . .
    H H1 0.2878 0.5045 0.7104 0.048 Uiso calc R 1 . .
    N N2 -0.0123(6) 0.67564(14) 0.90152(14) 0.0319(6) Uani d . 1 . .
    H H2A -0.1486 0.6668 0.9393 0.038 Uiso calc R 1 . .
    H H2B 0.1421 0.6729 0.9320 0.038 Uiso calc R 1 . .
    O O2 -0.0135(5) 0.82385(13) 1.00915(13) 0.0390(6) Uani d . 1 . .
    O O1 -0.2002(7) 0.91384(15) 0.90704(15) 0.0581(8) Uani d . 1 . .
    C C1 0.4997(7) 0.6110(2) 0.66226(19) 0.0382(8) Uani d . 1 . .
    C C2 0.6786(8) 0.5800(3) 0.59940(19) 0.0476(9) Uani d . 1 . .
    H H2 0.6826 0.5183 0.5830 0.057 Uiso calc R 1 . .
    C C3 0.8495(8) 0.6429(3) 0.5621(2) 0.0539(11) Uani d . 1 . .
    H H3 0.9745 0.6232 0.5209 0.065 Uiso calc R 1 . .
    C C4 0.8388(8) 0.7364(3) 0.5849(2) 0.0503(9) Uani d . 1 . .
    H H4 0.9523 0.7782 0.5574 0.060 Uiso calc R 1 . .
    C C5 0.6633(8) 0.7669(3) 0.6473(2) 0.0441(9) Uani d . 1 . .
    H H5 0.6573 0.8290 0.6622 0.053 Uiso calc R 1 . .
    C C6 0.4939(7) 0.7043(2) 0.68836(19) 0.0348(7) Uani d . 1 . .
    C C7 0.2982(7) 0.7105(2) 0.75634(17) 0.0343(8) Uani d . 1 . .
    C C8 0.2132(7) 0.7924(2) 0.8087(2) 0.0369(8) Uani d . 1 . .
    H H8A 0.1759 0.8437 0.7699 0.044 Uiso calc R 1 . .
    H H8B 0.3574 0.8105 0.8477 0.044 Uiso calc R 1 . .
    C C9 -0.0383(7) 0.7696(2) 0.86201(19) 0.0325(8) Uani d . 1 . .
    H H9 -0.1924 0.7690 0.8222 0.039 Uiso calc R 1 . .
    C C10 -0.0145(7) 0.59951(19) 0.83517(18) 0.0345(8) Uani d . 1 . .
    H H10 -0.1902 0.5989 0.8062 0.041 Uiso calc R 1 . .
    C C11 0.1945(8) 0.6245(2) 0.76945(19) 0.0348(8) Uani d . 1 . .
    C C12 0.0263(10) 0.5078(2) 0.8807(2) 0.0550(11) Uani d . 1 . .
    H H12A 0.1971 0.5078 0.9098 0.082 Uiso calc R 1 . .
    H H12B 0.0219 0.4591 0.8383 0.082 Uiso calc R 1 . .
    H H12C -0.1142 0.4986 0.9228 0.082 Uiso calc R 1 . .
    C C13 -0.0897(7) 0.8423(2) 0.9318(2) 0.0355(8) 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
    N1 0.0454(19) 0.0379(14) 0.0374(15) -0.0017(15) 0.0046(15) -0.0056(11)
    N2 0.0258(15) 0.0372(13) 0.0326(13) -0.0020(13) -0.0009(14) -0.0002(10)
    O2 0.0340(14) 0.0448(13) 0.0381(12) 0.0015(11) 0.0012(12) -0.0039(10)
    O1 0.076(2) 0.0457(14) 0.0523(14) 0.0215(15) 0.0009(15) 0.0018(12)
    C1 0.035(2) 0.0501(19) 0.0292(16) 0.0034(19) -0.0021(17) -0.0026(13)
    C2 0.048(2) 0.061(2) 0.0336(17) 0.011(2) 0.0031(19) -0.0081(17)
    C3 0.038(2) 0.087(3) 0.037(2) 0.005(2) 0.0069(19) -0.0038(19)
    C4 0.034(2) 0.079(3) 0.0377(18) -0.009(2) 0.0057(19) 0.0038(18)
    C5 0.038(2) 0.056(2) 0.0382(17) -0.0014(19) 0.0014(18) 0.0012(15)
    C6 0.0291(18) 0.0470(18) 0.0283(14) 0.0000(17) -0.0003(16) -0.0008(13)
    C7 0.032(2) 0.0406(17) 0.0303(16) -0.0006(15) -0.0002(16) -0.0013(12)
    C8 0.033(2) 0.0390(17) 0.0383(16) -0.0018(15) 0.0021(16) 0.0035(13)
    C9 0.026(2) 0.0388(17) 0.0324(15) 0.0009(14) 0.0005(15) 0.0017(13)
    C10 0.0354(19) 0.0374(17) 0.0306(16) -0.0050(17) 0.0013(17) -0.0018(12)
    C11 0.0312(19) 0.0412(18) 0.0319(15) 0.0003(15) -0.0038(15) -0.0034(13)
    C12 0.073(3) 0.041(2) 0.051(2) -0.001(2) 0.009(2) 0.0002(15)
    C13 0.0307(19) 0.0395(18) 0.0363(18) -0.0005(15) 0.0043(15) 0.0011(14)
_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
    N1 C1 . 1.383(4) ?
    N1 C11 . 1.388(4) ?
    N1 H1 . 0.8600 ?
    N2 C9 . 1.498(4) ?
    N2 C10 . 1.501(3) ?
    N2 H2A . 0.9000 ?
    N2 H2B . 0.9000 ?
    O2 C13 . 1.272(4) ?
    O1 C13 . 1.234(4) ?
    C1 C2 . 1.386(5) ?
    C1 C6 . 1.412(4) ?
    C2 C3 . 1.373(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.404(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.368(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.390(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.428(5) ?
    C7 C11 . 1.367(4) ?
    C7 C8 . 1.495(4) ?
    C8 C9 . 1.530(5) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C13 . 1.523(4) ?
    C9 H9 . 0.9800 ?
    C10 C11 . 1.492(4) ?
    C10 C12 . 1.516(4) ?
    C10 H10 . 0.9800 ?
    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
    C1 N1 C11 . . 108.2(3) ?
    C1 N1 H1 . . 125.9 ?
    C11 N1 H1 . . 125.9 ?
    C9 N2 C10 . . 113.4(2) ?
    C9 N2 H2A . . 108.9 ?
    C10 N2 H2A . . 108.9 ?
    C9 N2 H2B . . 108.9 ?
    C10 N2 H2B . . 108.9 ?
    H2A N2 H2B . . 107.7 ?
    N1 C1 C2 . . 130.2(3) ?
    N1 C1 C6 . . 108.2(3) ?
    C2 C1 C6 . . 121.4(3) ?
    C3 C2 C1 . . 118.1(3) ?
    C3 C2 H2 . . 121.0 ?
    C1 C2 H2 . . 121.0 ?
    C2 C3 C4 . . 121.1(3) ?
    C2 C3 H3 . . 119.5 ?
    C4 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 120.8(4) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 119.4(3) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C5 C6 C1 . . 119.1(3) ?
    C5 C6 C7 . . 134.5(3) ?
    C1 C6 C7 . . 106.3(3) ?
    C11 C7 C6 . . 107.8(3) ?
    C11 C7 C8 . . 122.8(3) ?
    C6 C7 C8 . . 129.4(3) ?
    C7 C8 C9 . . 110.2(3) ?
    C7 C8 H8A . . 109.6 ?
    C9 C8 H8A . . 109.6 ?
    C7 C8 H8B . . 109.6 ?
    C9 C8 H8B . . 109.6 ?
    H8A C8 H8B . . 108.1 ?
    N2 C9 C13 . . 111.3(2) ?
    N2 C9 C8 . . 110.0(3) ?
    C13 C9 C8 . . 111.2(3) ?
    N2 C9 H9 . . 108.1 ?
    C13 C9 H9 . . 108.1 ?
    C8 C9 H9 . . 108.1 ?
    C11 C10 N2 . . 105.8(2) ?
    C11 C10 C12 . . 115.5(3) ?
    N2 C10 C12 . . 109.5(2) ?
    C11 C10 H10 . . 108.6 ?
    N2 C10 H10 . . 108.6 ?
    C12 C10 H10 . . 108.6 ?
    C7 C11 N1 . . 109.4(3) ?
    C7 C11 C10 . . 125.8(3) ?
    N1 C11 C10 . . 124.9(3) ?
    C10 C12 H12A . . 109.5 ?
    C10 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C10 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    O1 C13 O2 . . 126.5(3) ?
    O1 C13 C9 . . 116.3(3) ?
    O2 C13 C9 . . 117.2(3) ?
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
    C11 N1 C1 C2 . . . . 177.1(3) ?
    C11 N1 C1 C6 . . . . 1.3(4) ?
    N1 C1 C2 C3 . . . . -176.0(3) ?
    C6 C1 C2 C3 . . . . -0.7(5) ?
    C1 C2 C3 C4 . . . . -1.8(5) ?
    C2 C3 C4 C5 . . . . 2.2(6) ?
    C3 C4 C5 C6 . . . . 0.0(6) ?
    C4 C5 C6 C1 . . . . -2.4(5) ?
    C4 C5 C6 C7 . . . . 177.5(4) ?
    N1 C1 C6 C5 . . . . 179.0(3) ?
    C2 C1 C6 C5 . . . . 2.8(5) ?
    N1 C1 C6 C7 . . . . -0.9(3) ?
    C2 C1 C6 C7 . . . . -177.1(3) ?
    C5 C6 C7 C11 . . . . -179.8(4) ?
    C1 C6 C7 C11 . . . . 0.1(4) ?
    C5 C6 C7 C8 . . . . -1.1(6) ?
    C1 C6 C7 C8 . . . . 178.8(3) ?
    C11 C7 C8 C9 . . . . -12.0(4) ?
    C6 C7 C8 C9 . . . . 169.5(3) ?
    C10 N2 C9 C13 . . . . 168.9(3) ?
    C10 N2 C9 C8 . . . . -67.4(3) ?
    C7 C8 C9 N2 . . . . 42.5(3) ?
    C7 C8 C9 C13 . . . . 166.2(3) ?
    C9 N2 C10 C11 . . . . 52.2(3) ?
    C9 N2 C10 C12 . . . . 177.2(3) ?
    C6 C7 C11 N1 . . . . 0.7(4) ?
    C8 C7 C11 N1 . . . . -178.1(3) ?
    C6 C7 C11 C10 . . . . 179.4(3) ?
    C8 C7 C11 C10 . . . . 0.6(5) ?
    C1 N1 C11 C7 . . . . -1.3(4) ?
    C1 N1 C11 C10 . . . . -180.0(3) ?
    N2 C10 C11 C7 . . . . -19.6(4) ?
    C12 C10 C11 C7 . . . . -140.9(4) ?
    N2 C10 C11 N1 . . . . 158.9(3) ?
    C12 C10 C11 N1 . . . . 37.6(4) ?
    N2 C9 C13 O1 . . . . -156.8(3) ?
    C8 C9 C13 O1 . . . . 80.3(4) ?
    N2 C9 C13 O2 . . . . 23.7(4) ?
    C8 C9 C13 O2 . . . . -99.2(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
    C10 H10 Cg1 1_655 0.98 2.69 3.644(3) 165
data_global
_journal_date_recd_electronic     2009-11-23
_journal_date_accepted     2010-01-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o446
_journal_page_last     o446
_journal_paper_category     QO
_journal_coeditor_code     PB2017
_publ_contact_author_name     'Prof. Sun, Xiao-Li,Prof. Tang, Hai-Feng '
_publ_contact_author_address
;
Department of Chemistry
School of Pharmacy
Fourth Military Medical University
Changle West Road 17, 710032, Xi-An
China
;
_publ_contact_author_email     'xiaoli sun@yahoo.cn, tanghaifeng71@163.com'
_publ_contact_author_fax     '+86-29-8477-6945'
_publ_contact_author_phone     '+86-29-8477-4470'
_publ_section_title
;
1-Methyl-1,2,3,4-tetrahydrocarbolin-2-ium-3-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Lu, Cheng-Tao' .
;
Department of Chemistry
School of Pharmacy
Fourth Military Medical University
Changle West Road 17, 710032 Xi-An
People's Republic of China
;
    'Jing, Lin-lin' .
;
Department of Chemistry
School of Pharmacy
Fourth Military Medical University
Changle West Road 17, 710032 Xi-An
People's Republic of China
;
    'Wang, Hai-Bo' .
;
Department of Chemistry
School of Pharmacy
Fourth Military Medical University
Changle West Road 17, 710032 Xi-An
People's Republic of China
;
    'Tang, Hai-Feng' .
;
Department of Pharmacy, Xijing Hospital
School of Pharmacy
Fourth Military Medical University
Changle West Road 17, 710032 Xi-An
People's Republic of China
;
    'Sun, Xiao-Li' .
;
Department of Chemistry
School of Pharmacy
Fourth Military Medical University
Changle West Road 17, 710032 Xi-An
People's Republic of China
;
_refine_ls_number_constraints     ?
