##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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_global
_journal_date_recd_electronic     2013-01-14
_journal_date_accepted     2013-02-21
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2013
_journal_volume     69
_journal_issue      4
_journal_page_first     403
_journal_page_last     406
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113005106
_journal_coeditor_code     SF3193
_publ_contact_author_name     'Carlos Basílio Pinheiro'
_publ_contact_author_address
;
Laboratório de Cristalografia
Departamento de Física
Universidade Federal de Minas Gerais
Avenida Antônio Carlos 6627
Belo Horizonte, MG-CEP 30.270-901
Brazil
;
_publ_contact_author_email     cbpinheiro@ufmg.br
_publ_contact_author_fax     '+55(31)34095600'
_publ_contact_author_phone     '+55(31)34096600'
_publ_section_title
;
The structure of the 1H-imidazol-3-ium lawsonate salt aided by ab
initio gas-phase calculations
;
loop_
    _publ_author_name
    _publ_author_address
    'Ribeiro, Marcos Antônio'
;
Departamento de Química
Universidade Federal de Minas Gerais
Avenida Antônio Carlos 6627
Belo Horizonte, MG-CEP 30.270-901
Brazil
;
    'Oliveira, Willian Xerxes Coelho'
;
Departamento de Química
Universidade Federal de Minas Gerais
Avenida Antônio Carlos 6627
Belo Horizonte, MG-CEP 30.270-901
Brazil
;
    'Stumpf, Humberto Osório'
;
Departamento de Química
Universidade Federal de Minas Gerais
Avenida Antônio Carlos 6627
Belo Horizonte, MG-CEP 30.270-901
Brazil
;
    'Pinheiro, Carlos Basílio'
;
Laboratório de Cristalografia
Departamento de Física
Universidade Federal de Minas Gerais
Avenida Antônio Carlos 6627
Belo Horizonte, MG-CEP 30.270-901
Brazil
;
data_I
_chemical_name_systematic
;
1H-Imidazol-3-ium 1,4-dioxo-1,4-dihydronaphthalen-2-olate
;
_chemical_formula_moiety     'C3 H5 N2 +, C10 H5 O3 -'
_chemical_formula_sum     'C13 H10 N2 O3'
_chemical_formula_iupac     'C3 H5 N2 + , C10 H5 O3 -'
_chemical_formula_weight     242.23
_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     4.77830(10)
_cell_length_b     10.7727(2)
_cell_length_c     22.9128(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1179.44(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5844
_cell_measurement_theta_min     3.8552
_cell_measurement_theta_max     66.5238
_cell_measurement_temperature     298(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.2822
_exptl_crystal_size_mid     0.2121
_exptl_crystal_size_min     0.1226
_exptl_crystal_density_diffrn     1.364
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     504
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    2 1 -8 0.0655
    -2 -1 -12 0.0648
    1 -3 13 0.0804
    0 7 -3 0.1116
    -2 -5 7 0.1375
    -2 -1 8 0.1065
    -2 3 7 0.1113
    1 2 14 0.0613
    -1 -1 14 0.0653
    -1 -2 -14 0.0613
    0 -7 3 0.1116
_exptl_absorpt_coefficient_mu     0.826
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details     '(CrysAlisPro; Agilent, 2012)'
_exptl_absorpt_correction_T_min     0.861
_exptl_absorpt_correction_T_max     0.924
_exptl_special_details     ?
_diffrn_ambient_temperature     298.0(10)
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_source     'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type
               'Oxford Xcalibur Gemini Ultra diffractometer with Atlas detector'
_diffrn_measurement_method     w
_diffrn_detector_area_resol_mean     10.4186
_diffrn_reflns_number     10612
_diffrn_reflns_av_R_equivalents     0.0619
_diffrn_reflns_theta_min     3.86
_diffrn_reflns_theta_max     66.63
_diffrn_reflns_theta_full     66.63
_diffrn_measured_fraction_theta_max     1
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_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     2091
_reflns_number_gt     1966
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0371
_refine_ls_R_factor_gt     0.0347
_refine_ls_wR_factor_gt     0.085
_refine_ls_wR_factor_ref     0.0879
_refine_ls_goodness_of_fit_ref     1.051
_refine_ls_restrained_S_all     1.051
_refine_ls_number_reflns     2091
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0499P)²+0.0821P] 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
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.164
_refine_diff_density_min     -0.118
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0032(6)
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details
                                    'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack     0.1(2)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP (Sheldrick, 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O4 -0.0065(3) 0.23173(10) 0.36739(6) 0.0582(4) Uani d . 1 1 . .
    O O2 0.6384(3) 0.53669(11) 0.31088(5) 0.0545(3) Uani d . 1 1 . .
    O O1 0.4704(3) 0.67443(11) 0.40191(5) 0.0574(4) Uani d . 1 1 . .
    C C9 0.0664(4) 0.59711(15) 0.48453(7) 0.0435(4) Uani d . 1 1 . .
    H H9 0.1469 0.6746 0.4907 0.052 Uiso calc R 1 1 . .
    C C5 0.0249(3) 0.40963(14) 0.42746(6) 0.0376(3) Uani d . 1 1 . .
    C C2 0.4506(3) 0.49163(14) 0.34490(7) 0.0406(3) Uani d . 1 1 . .
    C C3 0.3269(4) 0.37835(15) 0.33886(7) 0.0454(4) Uani d . 1 1 . .
    H H3 0.387 0.3277 0.3085 0.054 Uiso calc R 1 1 . .
    C C10 0.1470(3) 0.52621(13) 0.43676(6) 0.0369(3) Uani d . 1 1 . .
    C C6 -0.1761(4) 0.36641(16) 0.46604(7) 0.0451(4) Uani d . 1 1 . .
    H H6 -0.26 0.2897 0.4598 0.054 Uiso calc R 1 1 . .
    C C7 -0.2525(4) 0.43715(17) 0.51387(7) 0.0499(4) Uani d . 1 1 . .
    H H7 -0.3844 0.407 0.5401 0.06 Uiso calc R 1 1 . .
    C C8 -0.1327(4) 0.55279(16) 0.52275(7) 0.0492(4) Uani d . 1 1 . .
    H H8 -0.1869 0.6006 0.5546 0.059 Uiso calc R 1 1 . .
    C C1 0.3623(4) 0.57319(13) 0.39573(6) 0.0395(3) Uani d . 1 1 . .
    C C4 0.1112(4) 0.33248(13) 0.37613(7) 0.0421(4) Uani d . 1 1 . .
    N N1 0.1010(3) 0.25871(13) 0.18337(6) 0.0481(4) Uani d . 1 1 . .
    N N2 -0.1444(3) 0.40035(13) 0.22501(6) 0.0483(3) Uani d . 1 1 . .
    C C12 -0.0294(5) 0.45191(17) 0.17647(8) 0.0583(5) Uani d . 1 1 . .
    H H12 -0.0527 0.5331 0.1636 0.07 Uiso calc R 1 1 . .
    C C13 0.1243(5) 0.36318(18) 0.15059(8) 0.0596(5) Uani d . 1 1 . .
    H H13 0.2277 0.3718 0.1165 0.072 Uiso calc R 1 1 . .
    C C11 -0.0612(4) 0.28451(16) 0.22807(7) 0.0500(4) Uani d . 1 1 . .
    H H11 -0.1097 0.229 0.2575 0.06 Uiso calc R 1 1 . .
    H H1 0.194(6) 0.190(2) 0.1794(11) 0.075 Uiso d . 1 1 . .
    H H2 -0.243(5) 0.445(2) 0.2525(12) 0.075 Uiso d . 1 1 . .
_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
    O4 C4 . 1.2387(19) ?
    O2 C2 . 1.284(2) ?
    O1 C1 . 1.2151(19) ?
    C9 C8 . 1.378(2) ?
    C9 C10 . 1.389(2) ?
    C9 H9 . 0.93 ?
    C5 C6 . 1.386(2) ?
    C5 C10 . 1.401(2) ?
    C5 C4 . 1.498(2) ?
    C2 C3 . 1.363(2) ?
    C2 C1 . 1.519(2) ?
    C3 C4 . 1.427(2) ?
    C3 H3 . 0.93 ?
    C10 C1 . 1.483(2) ?
    C6 C7 . 1.384(3) ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.386(3) ?
    C7 H7 . 0.93 ?
    C8 H8 . 0.93 ?
    N1 C11 . 1.314(2) ?
    N1 C13 . 1.358(2) ?
    N1 H1 . 0.87(3) ?
    N2 C11 . 1.312(2) ?
    N2 C12 . 1.359(2) ?
    N2 H2 . 0.92(3) ?
    C12 C13 . 1.343(3) ?
    C12 H12 . 0.93 ?
    C13 H13 . 0.93 ?
    C11 H11 . 0.93 ?
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 C9 C10 . . 120.10(15) ?
    C8 C9 H9 . . 119.9 ?
    C10 C9 H9 . . 120 ?
    C6 C5 C10 . . 119.51(14) ?
    C6 C5 C4 . . 120.34(14) ?
    C10 C5 C4 . . 120.15(14) ?
    O2 C2 C3 . . 125.45(14) ?
    O2 C2 C1 . . 116.17(13) ?
    C3 C2 C1 . . 118.37(14) ?
    C2 C3 C4 . . 124.24(14) ?
    C2 C3 H3 . . 117.9 ?
    C4 C3 H3 . . 117.9 ?
    C9 C10 C5 . . 119.82(15) ?
    C9 C10 C1 . . 120.29(14) ?
    C5 C10 C1 . . 119.89(13) ?
    C7 C6 C5 . . 120.18(16) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C6 C7 C8 . . 120.17(16) ?
    C6 C7 H7 . . 119.9 ?
    C8 C7 H7 . . 119.9 ?
    C9 C8 C7 . . 120.20(15) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    O1 C1 C10 . . 121.83(14) ?
    O1 C1 C2 . . 119.37(14) ?
    C10 C1 C2 . . 118.79(13) ?
    O4 C4 C3 . . 122.33(14) ?
    O4 C4 C5 . . 119.21(15) ?
    C3 C4 C5 . . 118.46(13) ?
    C11 N1 C13 . . 107.71(15) ?
    C11 N1 H1 . . 124.3(17) ?
    C13 N1 H1 . . 127.4(17) ?
    C11 N2 C12 . . 108.06(15) ?
    C11 N2 H2 . . 128.2(16) ?
    C12 N2 H2 . . 123.3(16) ?
    C13 C12 N2 . . 106.94(16) ?
    C13 C12 H12 . . 126.5 ?
    N2 C12 H12 . . 126.5 ?
    C12 C13 N1 . . 107.51(16) ?
    C12 C13 H13 . . 126.2 ?
    N1 C13 H13 . . 126.2 ?
    N1 C11 N2 . . 109.78(15) ?
    N1 C11 H11 . . 125.1 ?
    N2 C11 H11 . . 125.1 ?
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_645 0.87(3) 2.46(3) 2.9726(19) 118(2)
    N1 H1 O2 3_645 0.87(3) 1.85(3) 2.6999(19) 166(3)
    N2 H2 O2 1_455 0.92(3) 1.76(3) 2.6658(17) 168(2)
    C12 H12 O4 3 0.93 2.27 3.182(2) 166.0
    C11 H11 O4 . 0.93 2.57 3.253(2) 130.9
