##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_publ_contact_author_name     'Carl Henrik Görbitz'
_publ_contact_author_address
;
Department of Chemistry
University of Oslo
Post Box 1033
Blindern 0315
Norway
;
_publ_contact_author_email     c.h.gorbitz@kjemi.uio.no
_publ_contact_author_fax     '(+47) 228 55 441'
_publ_contact_author_phone     ?
_publ_section_title
;
A supramolecular ladder-like network from trimesic acid and pyrazine
N,N'-dioxide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yadav, Vitthal N.' .
;
Department of Chemistry
University of Oslo
Post Box 1033
Blindern 0315
Norway
;
    'Görbitz, Carl Henrik' .
;
Department of Chemistry
University of Oslo
Post Box 1033
Blindern 0315
Norway
;
_publ_section_synopsis
;
Cocrystallized trimesic acid (TMA) and pyrazine N,N'-dioxide
(PNO) molecules form strong O---H...O hydrogen bonds, but also important weak
C---H...O and dipole--dipole intermolecular interactions to generate a densely
packed three-dimensional network.
;
_database_code_depnum_ccdc_archive     'CCDC 942551'
_chemical_name_systematic
;
Benzene-1,3,5-tricarboxylic acid--pyrazine N,N'-dioxide (2/1)
;
_chemical_name_common
                      'Trimesic acid--pyrazine N,N'-dioxide (2/1)'
_chemical_formula_moiety     'C9 H6 O6, 0.5(C4 H4 N2 O2)'
_chemical_formula_sum     'C11 H8 N O7'
_chemical_formula_iupac     'C9 H6 O6, 0.5C4 H4 N2 O2'
_chemical_formula_weight     266.18
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.9521(2)
_cell_length_b     8.0939(2)
_cell_length_c     8.6271(2)
_cell_angle_alpha     78.6210(10)
_cell_angle_beta     80.7000(10)
_cell_angle_gamma     79.7690(10)
_cell_volume     531.07(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5692
_cell_measurement_theta_min     2.43
_cell_measurement_theta_max     37.37
_cell_measurement_temperature     105(2)
_cell_special_details     centrosymmetric
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.90
_exptl_crystal_size_mid     0.55
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.665
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     274
_exptl_absorpt_coefficient_mu     0.143
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.910
_exptl_absorpt_correction_T_max     0.961
_exptl_special_details     ?
_diffrn_ambient_temperature     105(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     8.3
_diffrn_reflns_number     8828
_diffrn_reflns_av_R_equivalents     0.0110
_diffrn_reflns_av_sigmaI/netI     0.0171
_diffrn_reflns_theta_min     2.43
_diffrn_reflns_theta_max     37.56
_diffrn_reflns_theta_full     28.69
_diffrn_measured_fraction_theta_max     0.850
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_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     5615
_reflns_number_gt     4246
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0399
_refine_ls_R_factor_gt     0.0358
_refine_ls_wR_factor_gt     0.1042
_refine_ls_wR_factor_ref     0.1081
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     4773
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0677P)²+0.0833P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.596
_refine_diff_density_min     -0.279
_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'
    '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, 2013)'
_computing_cell_refinement     'APEX2 (Bruker, 2013)'
_computing_data_reduction     'APEX2 (Bruker, 2013)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (Macrae et al., 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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.20981(6) 0.51187(6) 0.45416(6) 0.01528(9) Uani d 1 . .
    H H1 0.145(2) 0.574(2) 0.376(2) 0.048(4) Uiso d 1 . .
    O O2 0.34003(7) 0.40854(8) 0.23656(6) 0.02106(11) Uani d 1 . .
    O O3 0.86133(7) -0.02322(7) 0.28510(6) 0.01846(10) Uani d 1 . .
    H H3 0.925(2) -0.124(2) 0.2599(19) 0.044(4) Uiso d 1 . .
    O O4 0.91678(6) -0.16621(6) 0.52724(6) 0.01699(10) Uani d 1 . .
    O O5 0.39074(8) 0.30350(9) 0.96259(7) 0.02744(13) Uani d 1 . .
    H H5 0.394(3) 0.318(2) 1.066(2) 0.061(5) Uiso d 1 . .
    O O6 0.64278(8) 0.13485(8) 0.99820(7) 0.02502(12) Uani d 1 . .
    C C1 0.45276(7) 0.29798(7) 0.48226(7) 0.01228(10) Uani d 1 . .
    C C2 0.58822(8) 0.18875(8) 0.41343(7) 0.01300(10) Uani d 1 . .
    H H21 0.5998(16) 0.1842(16) 0.2972(15) 0.020(3) Uiso d 1 . .
    C C3 0.70115(8) 0.08024(7) 0.51068(7) 0.01255(10) Uani d 1 . .
    C C4 0.68177(8) 0.08335(8) 0.67383(8) 0.01434(11) Uani d 1 . .
    H H41 0.7613(16) 0.0065(15) 0.7433(14) 0.021(3) Uiso d 1 . .
    C C5 0.54824(8) 0.19486(8) 0.74090(7) 0.01400(10) Uani d 1 . .
    C C6 0.43213(8) 0.30052(8) 0.64503(7) 0.01384(10) Uani d 1 . .
    H H61 0.3369(16) 0.3745(16) 0.6957(15) 0.022(3) Uiso d 1 . .
    C C7 0.32978(8) 0.40975(8) 0.37898(7) 0.01312(10) Uani d 1 . .
    C C8 0.83793(8) -0.04822(8) 0.44402(8) 0.01324(10) Uani d 1 . .
    C C9 0.53451(9) 0.20538(9) 0.91312(8) 0.01750(12) Uani d 1 . .
    O O7 0.02426(7) 0.67750(7) 0.22425(6) 0.01941(11) Uani d 1 . .
    C C10 0.04339(9) 0.65945(8) -0.04215(8) 0.01675(11) Uani d 1 . .
    H H10 0.0772(16) 0.7677(16) -0.0657(15) 0.023(3) Uiso d 1 . .
    C C11 -0.02925(9) 0.43131(8) 0.15687(8) 0.01661(11) Uani d 1 . .
    H H11 -0.0446(18) 0.3884(17) 0.2701(16) 0.030(3) Uiso d 1 . .
    N N1 0.01283(7) 0.59084(7) 0.11436(7) 0.01432(10) Uani d 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
    O1 C7 . 1.3212(8) ?
    O1 H1 . 0.928(18) ?
    O2 C7 . 1.2200(8) ?
    O3 C8 . 1.3330(8) ?
    O3 H3 . 0.929(17) ?
    O4 C8 . 1.2177(8) ?
    O5 C9 . 1.3318(9) ?
    O5 H5 . 0.931(19) ?
    O6 C9 . 1.2125(9) ?
    C1 C6 . 1.3910(9) ?
    C1 C2 . 1.3988(8) ?
    C1 C7 . 1.4893(8) ?
    C2 C3 . 1.3980(8) ?
    C2 H21 . 0.999(12) ?
    C3 C4 . 1.3957(9) ?
    C3 C8 . 1.4923(8) ?
    C4 C5 . 1.3942(9) ?
    C4 H41 . 0.991(13) ?
    C5 C6 . 1.3982(9) ?
    C5 C9 . 1.4902(9) ?
    C6 H61 . 0.979(13) ?
    O7 N1 . 1.3083(7) ?
    C10 N1 . 1.3552(9) ?
    C10 C11 2_565 1.3727(10) ?
    C10 H10 . 0.937(13) ?
    C11 N1 . 1.3567(9) ?
    C11 C10 2_565 1.3727(10) ?
    C11 H11 . 0.965(14) ?
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
    C7 O1 H1 . . 104.8(10) ?
    C8 O3 H3 . . 104.6(10) ?
    C9 O5 H5 . . 109.4(13) ?
    C6 C1 C2 . . 120.45(6) ?
    C6 C1 C7 . . 120.56(5) ?
    C2 C1 C7 . . 118.98(5) ?
    C3 C2 C1 . . 119.16(6) ?
    C3 C2 H21 . . 120.7(7) ?
    C1 C2 H21 . . 120.1(7) ?
    C4 C3 C2 . . 120.56(6) ?
    C4 C3 C8 . . 118.69(5) ?
    C2 C3 C8 . . 120.65(6) ?
    C5 C4 C3 . . 119.86(6) ?
    C5 C4 H41 . . 119.3(7) ?
    C3 C4 H41 . . 120.8(7) ?
    C4 C5 C6 . . 119.85(6) ?
    C4 C5 C9 . . 119.65(6) ?
    C6 C5 C9 . . 120.45(6) ?
    C1 C6 C5 . . 120.07(6) ?
    C1 C6 H61 . . 121.6(7) ?
    C5 C6 H61 . . 118.3(7) ?
    O2 C7 O1 . . 122.79(6) ?
    O2 C7 C1 . . 122.86(6) ?
    O1 C7 C1 . . 114.35(5) ?
    O4 C8 O3 . . 123.68(6) ?
    O4 C8 C3 . . 123.04(6) ?
    O3 C8 C3 . . 113.25(5) ?
    O6 C9 O5 . . 123.72(7) ?
    O6 C9 C5 . . 124.02(6) ?
    O5 C9 C5 . . 112.26(6) ?
    N1 C10 C11 . 2_565 120.04(6) ?
    N1 C10 H10 . . 116.6(8) ?
    C11 C10 H10 2_565 . 123.3(8) ?
    N1 C11 C10 . 2_565 120.26(6) ?
    N1 C11 H11 . . 115.4(8) ?
    C10 C11 H11 2_565 . 124.3(8) ?
    O7 N1 C10 . . 120.30(6) ?
    O7 N1 C11 . . 120.00(6) ?
    C10 N1 C11 . . 119.69(6) ?
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
    C6 C1 C2 C3 . . . . 0.96(9) ?
    C7 C1 C2 C3 . . . . -178.25(5) ?
    C1 C2 C3 C4 . . . . -1.49(9) ?
    C1 C2 C3 C8 . . . . 174.80(5) ?
    C2 C3 C4 C5 . . . . 0.34(9) ?
    C8 C3 C4 C5 . . . . -176.03(5) ?
    C3 C4 C5 C6 . . . . 1.35(9) ?
    C3 C4 C5 C9 . . . . -176.25(6) ?
    C2 C1 C6 C5 . . . . 0.71(9) ?
    C7 C1 C6 C5 . . . . 179.91(6) ?
    C4 C5 C6 C1 . . . . -1.87(10) ?
    C9 C5 C6 C1 . . . . 175.71(6) ?
    C6 C1 C7 O2 . . . . -177.97(6) ?
    C2 C1 C7 O2 . . . . 1.24(10) ?
    C6 C1 C7 O1 . . . . 2.80(9) ?
    C2 C1 C7 O1 . . . . -177.99(5) ?
    C4 C3 C8 O4 . . . . 11.04(9) ?
    C2 C3 C8 O4 . . . . -165.32(6) ?
    C4 C3 C8 O3 . . . . -170.67(6) ?
    C2 C3 C8 O3 . . . . 12.97(8) ?
    C4 C5 C9 O6 . . . . 7.68(11) ?
    C6 C5 C9 O6 . . . . -169.91(7) ?
    C4 C5 C9 O5 . . . . -173.32(6) ?
    C6 C5 C9 O5 . . . . 9.09(10) ?
    C11 C10 N1 O7 2_565 . . . -179.25(6) ?
    C11 C10 N1 C11 2_565 . . . 0.96(11) ?
    C10 C11 N1 O7 2_565 . . . 179.24(6) ?
    C10 C11 N1 C10 2_565 . . . -0.97(11) ?
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
    O1 H1 O7 . 0.928(18) 1.739(18) 2.6651(7) 175.9(16)
    O3 H3 O7 1_645 0.929(17) 1.719(17) 2.6437(7) 173.6(15)
    O5 H5 O2 1_556 0.931(19) 1.73(2) 2.6144(8) 158.0(19)
    C10 H10 O3 2_665 0.937(13) 2.571(13) 3.3883(8) 145.9(10)
    C11 H11 O4 2_656 0.965(14) 2.451(14) 3.2603(8) 141.2(11)
data_TMA-PNO
_journal_date_recd_electronic     2013-11-15
_journal_date_accepted     2013-12-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2014
_journal_volume     70
_journal_issue      1
_journal_page_first     43
_journal_page_last     45
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113032733
_journal_coeditor_code     GZ3247
