##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2004-10-06
_journal_date_accepted     2004-11-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2491
_journal_page_last     o2492
_journal_paper_category     EO
_publ_contact_author_name     'Dr. Elena V. Karpova'
_publ_contact_author_address
;
  Inorganic Chemistry Division
  Chemistry Department
  Moscow State University
  119992 Leninskie Gory 1-3
  Moscow
  Russia
;
_publ_contact_author_email     karpova@inorg.chem.msu.ru
_publ_contact_author_fax     '7 (095) 939 09 98'
_publ_contact_author_phone     '7 (095) 939 28 70'
_publ_section_title
;
Bis(dimethylammonium) terephthalate
;
loop_
    _publ_author_name
    _publ_author_address
    'Karpova, Elena V.'
;
Inorganic Chemistry Division
Chemistry Department
Moscow State University
119992 Leninskie Gory 1-3
Moscow
Russia
;
    'Zakharov, Maxim A.'
;
General Chemistry Division
Chemistry Department
Moscow State University
119992 Leninskie Gory 1-3
Moscow
Russia
;
    'Gutnikov, Sergey I.'
;
High School of Material Science
Moscow State University
119992 Leninskie Gory
Moscow
Russia
;
    'Alekseyev, Roman S.'
;
Inorganic Chemistry Division
Chemistry Department
Moscow State University
119992 Leninskie Gory 1-3
Moscow
Russia
;
data_I
_audit_creation_method     'WinGX (Farrugia, L.J., 1999)'
_chemical_name_systematic     'bis(dimethylammonium) terephtalate'
_chemical_name_common     ?
_chemical_formula_moiety     '2C2 H8 N +, C8 H4 O4 2-'
_chemical_formula_sum     'C12 H20 N2 O4'
_chemical_formula_iupac     '2C2 H8 N +, C8 H4 O4 2-'
_chemical_formula_weight     256.30
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.642(2)
_cell_length_b     11.103(2)
_cell_length_c     13.272(3)
_cell_angle_alpha     90
_cell_angle_beta     91.01(3)
_cell_angle_gamma     90
_cell_volume     1420.6(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20
_cell_measurement_theta_min     10
_cell_measurement_theta_max     14
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.5
_exptl_crystal_size_mid     0.3
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.198
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.968
_exptl_absorpt_correction_T_max     0.982
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     293(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'non-profiled ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2910
_diffrn_reflns_av_R_equivalents     0.050
_diffrn_reflns_av_sigmaI/netI     0.052
_diffrn_reflns_theta_min     2.4
_diffrn_reflns_theta_max     26.0
_diffrn_reflns_theta_full     26.0
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     7200
_diffrn_standards_decay_%     1
_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     2790
_reflns_number_gt     1759
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.097
_refine_ls_R_factor_gt     0.053
_refine_ls_wR_factor_gt     0.121
_refine_ls_wR_factor_ref     0.134
_refine_ls_goodness_of_fit_ref     1.05
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     2790
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0626P)²+0.1137P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.20
_refine_diff_density_min     -0.23
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.083(7)
_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     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'DIAMOND (2000)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1 0.16949(16) 0.32520(16) 0.30168(11) 0.0503(5) Uani d . 1 . . O
    O2 0.32915(15) 0.37168(15) 0.41691(12) 0.0518(5) Uani d . 1 . . O
    O3 -0.23902(17) 0.18343(17) 0.34577(14) 0.0607(5) Uani d . 1 . . O
    O4 -0.35178(17) 0.12149(19) 0.47936(13) 0.0697(6) Uani d . 1 . . O
    N1 0.4891(2) 0.23523(19) 0.29320(14) 0.0428(5) Uani d D 1 . . N
    N2 0.0194(2) 0.2716(2) 0.13398(17) 0.0504(6) Uani d . 1 . . N
    C1 0.0995(2) 0.43806(18) 0.44428(14) 0.0315(5) Uani d . 1 . . C
    C2 0.2069(2) 0.37309(19) 0.38263(15) 0.0349(5) Uani d . 1 . . C
    C3 0.1391(2) 0.51530(19) 0.52135(15) 0.0376(5) Uani d . 1 . . C
    H3 0.2329 0.5263 0.5362 0.045 Uiso calc R 1 . . H
    C4 0.0413(2) 0.5763(2) 0.57671(15) 0.0368(5) Uani d . 1 . . C
    H4 0.0700 0.6275 0.6285 0.044 Uiso calc R 1 . . H
    C5 -0.2453(2) 0.1282(2) 0.42708(17) 0.0432(6) Uani d . 1 . . C
    C6 -0.1171(2) 0.06183(19) 0.46475(14) 0.0337(5) Uani d . 1 . . C
    C7 0.0122(2) 0.0890(2) 0.42851(16) 0.0395(5) Uani d . 1 . . C
    H7 0.0215 0.1491 0.3802 0.047 Uiso calc R 1 . . H
    C8 -0.1276(2) -0.0281(2) 0.53679(15) 0.0394(5) Uani d . 1 . . C
    H8 -0.2141 -0.0475 0.5620 0.047 Uiso calc R 1 . . H
    C9 0.4241(3) 0.1145(2) 0.2916(2) 0.0625(7) Uani d . 1 . . C
    H9A 0.3284 0.1217 0.2713 0.094 Uiso calc R 1 . . H
    H9B 0.4302 0.0797 0.3578 0.094 Uiso calc R 1 . . H
    H9C 0.4715 0.0639 0.2448 0.094 Uiso calc R 1 . . H
    C10 0.4904(3) 0.2906(3) 0.1931(2) 0.0892(11) Uani d . 1 . . C
    H10A 0.5402 0.2397 0.1478 0.134 Uiso calc R 1 . . H
    H10B 0.5350 0.3678 0.1973 0.134 Uiso calc R 1 . . H
    H10C 0.3968 0.3006 0.1686 0.134 Uiso calc R 1 . . H
    C11 -0.1256(3) 0.3116(3) 0.1309(2) 0.0654(8) Uani d . 1 . . C
    H11A -0.1704 0.2817 0.0708 0.098 Uiso calc R 1 . . H
    H11B -0.1289 0.3980 0.1311 0.098 Uiso calc R 1 . . H
    H11C -0.1725 0.2811 0.1889 0.098 Uiso calc R 1 . . H
    C12 0.0327(4) 0.1401(3) 0.1284(2) 0.0873(11) Uani d . 1 . . C
    H12A -0.0112 0.1042 0.1854 0.131 Uiso calc R 1 . . H
    H12B 0.1291 0.1185 0.1287 0.131 Uiso calc R 1 . . H
    H12C -0.0112 0.1115 0.0675 0.131 Uiso calc R 1 . . H
    H1 0.063(3) 0.302(2) 0.193(2) 0.072(9) Uiso d . 1 . . H
    H2 0.069(3) 0.311(3) 0.075(2) 0.091(10) Uiso d . 1 . . H
    H5 0.5818(18) 0.229(2) 0.3170(17) 0.055(7) Uiso d D 1 . . H
    H6 0.441(3) 0.287(2) 0.338(2) 0.076(9) Uiso d . 1 . . H
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 0.0443(9) 0.0688(11) 0.0377(9) 0.0084(8) -0.0023(7) -0.0173(8)
    O2 0.0370(9) 0.0671(12) 0.0511(9) 0.0134(8) -0.0057(7) -0.0177(8)
    O3 0.0443(10) 0.0714(13) 0.0660(11) 0.0039(9) -0.0115(8) 0.0238(10)
    O4 0.0439(10) 0.1062(16) 0.0591(11) 0.0286(10) 0.0056(9) -0.0001(10)
    N1 0.0350(10) 0.0519(13) 0.0415(11) 0.0100(9) 0.0007(8) 0.0033(9)
    N2 0.0489(12) 0.0621(14) 0.0400(12) -0.0020(10) -0.0062(10) -0.0033(10)
    C1 0.0323(10) 0.0317(11) 0.0303(10) 0.0027(9) 0.0007(8) 0.0015(9)
    C2 0.0376(11) 0.0352(12) 0.0319(11) 0.0035(9) -0.0012(9) 0.0012(9)
    C3 0.0288(10) 0.0441(13) 0.0396(12) -0.0013(9) -0.0011(9) -0.0034(10)
    C4 0.0368(11) 0.0401(12) 0.0333(11) -0.0002(10) -0.0019(9) -0.0070(10)
    C5 0.0410(13) 0.0447(13) 0.0436(13) 0.0039(10) -0.0067(11) -0.0061(11)
    C6 0.0315(10) 0.0383(12) 0.0311(10) 0.0006(9) -0.0025(8) -0.0053(9)
    C7 0.0426(13) 0.0410(13) 0.0350(11) -0.0030(10) 0.0005(9) 0.0065(10)
    C8 0.0278(10) 0.0531(14) 0.0373(11) -0.0054(10) 0.0042(9) 0.0008(10)
    C9 0.0501(15) 0.0611(18) 0.0760(18) 0.0013(13) -0.0032(13) -0.0112(14)
    C10 0.073(2) 0.127(3) 0.0679(19) 0.022(2) 0.0125(16) 0.051(2)
    C11 0.0483(15) 0.086(2) 0.0621(17) 0.0076(14) -0.0070(13) -0.0018(15)
    C12 0.115(3) 0.074(2) 0.073(2) 0.0221(19) -0.0329(19) -0.0171(17)
_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 C2 . 1.246(2) no
    O2 C2 . 1.256(2) no
    O3 C5 . 1.244(3) no
    O4 C5 . 1.252(3) no
    N1 C10 . 1.464(3) no
    N1 C9 . 1.480(3) no
    N1 H5 . 0.946(16) no
    N1 H6 . 0.96(3) no
    N2 C11 . 1.467(3) no
    N2 C12 . 1.468(4) no
    N2 H1 . 0.95(3) no
    N2 H2 . 1.02(3) no
    C1 C3 . 1.383(3) no
    C1 C4 3_566 1.390(3) no
    C1 C2 . 1.514(3) no
    C3 C4 . 1.383(3) no
    C3 H3 . 0.9300 no
    C4 H4 . 0.9300 no
    C5 C6 . 1.516(3) no
    C6 C7 . 1.378(3) no
    C6 C8 . 1.388(3) no
    C7 C8 3_556 1.374(3) no
    C7 H7 . 0.9300 no
    C8 H8 . 0.9300 no
    C9 H9A . 0.9600 no
    C9 H9B . 0.9600 no
    C9 H9C . 0.9600 no
    C10 H10A . 0.9600 no
    C10 H10B . 0.9600 no
    C10 H10C . 0.9600 no
    C11 H11A . 0.9600 no
    C11 H11B . 0.9600 no
    C11 H11C . 0.9600 no
    C12 H12A . 0.9600 no
    C12 H12B . 0.9600 no
    C12 H12C . 0.9600 no
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
    C10 N1 C9 . . 112.2(2) no
    C10 N1 H5 . . 108.2(15) no
    C9 N1 H5 . . 109.5(14) no
    C10 N1 H6 . . 109.0(17) no
    C9 N1 H6 . . 110.2(16) no
    H5 N1 H6 . . 108(2) no
    C11 N2 C12 . . 112.5(2) no
    C11 N2 H1 . . 109.0(17) no
    C12 N2 H1 . . 111.3(16) no
    C11 N2 H2 . . 107.9(17) no
    C12 N2 H2 . . 110.3(18) no
    H1 N2 H2 . . 105(2) no
    C3 C1 C4 . 3_566 118.36(18) no
    C3 C1 C2 . . 120.85(18) no
    C4 C1 C2 3_566 . 120.77(18) no
    O1 C2 O2 . . 124.20(19) no
    O1 C2 C1 . . 118.64(18) no
    O2 C2 C1 . . 117.16(18) no
    C4 C3 C1 . . 120.99(18) no
    C4 C3 H3 . . 119.5 no
    C1 C3 H3 . . 119.5 no
    C3 C4 C1 . 3_566 120.67(18) no
    C3 C4 H4 . . 119.7 no
    C1 C4 H4 3_566 . 119.7 no
    O3 C5 O4 . . 124.3(2) no
    O3 C5 C6 . . 118.3(2) no
    O4 C5 C6 . . 117.4(2) no
    C7 C6 C8 . . 118.41(19) no
    C7 C6 C5 . . 121.04(19) no
    C8 C6 C5 . . 120.54(19) no
    C8 C7 C6 3_556 . 120.5(2) no
    C8 C7 H7 3_556 . 119.8 no
    C6 C7 H7 . . 119.8 no
    C7 C8 C6 3_556 . 121.12(19) no
    C7 C8 H8 3_556 . 119.4 no
    C6 C8 H8 . . 119.4 no
    N1 C9 H9A . . 109.5 no
    N1 C9 H9B . . 109.5 no
    H9A C9 H9B . . 109.5 no
    N1 C9 H9C . . 109.5 no
    H9A C9 H9C . . 109.5 no
    H9B C9 H9C . . 109.5 no
    N1 C10 H10A . . 109.5 no
    N1 C10 H10B . . 109.5 no
    H10A C10 H10B . . 109.5 no
    N1 C10 H10C . . 109.5 no
    H10A C10 H10C . . 109.5 no
    H10B C10 H10C . . 109.5 no
    N2 C11 H11A . . 109.5 no
    N2 C11 H11B . . 109.5 no
    H11A C11 H11B . . 109.5 no
    N2 C11 H11C . . 109.5 no
    H11A C11 H11C . . 109.5 no
    H11B C11 H11C . . 109.5 no
    N2 C12 H12A . . 109.5 no
    N2 C12 H12B . . 109.5 no
    H12A C12 H12B . . 109.5 no
    N2 C12 H12C . . 109.5 no
    H12A C12 H12C . . 109.5 no
    H12B C12 H12C . . 109.5 no
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 H5 O3 1_655 0.95(2) 1.83(2) 2.761(3) 167(2) yes
    N1 H6 O2 . 0.96(3) 1.78(3) 2.731(3) 171(2) yes
    N2 H1 O1 . 0.95(3) 1.77(3) 2.700(3) 165(2) yes
    N2 H2 O4 4_665 1.02(3) 1.68(3) 2.693(3) 179(3) yes
