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The asymmetric unit of the title compound, 2C2H8N+·C8H4O42−, comprises two crystallographically independent dimethylammonium cations and two half-terephthalate anions. The latter are each disposed about an inversion centre. N—H...O hydrogen bonds link the ions into a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028685/tk6190sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028685/tk6190Isup2.hkl
Contains datablock I

CCDC reference: 259857

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.134
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for N1
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N2 PLAT353_ALERT_3_C Long N-H Bond (0.87A) N2 - H2 ... 1.02 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (2000); software used to prepare material for publication: WinGX (Farrugia, 1999).

bis(dimethylammonium) terephtalate top
Crystal data top
2C2H8N+·C8H4O42F(000) = 552
Mr = 256.30Dx = 1.198 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 20 reflections
a = 9.642 (2) Åθ = 10–14°
b = 11.103 (2) ŵ = 0.09 mm1
c = 13.272 (3) ÅT = 293 K
β = 91.01 (3)°Prism, colourless
V = 1420.6 (5) Å30.5 × 0.3 × 0.2 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1759 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 26.0°, θmin = 2.4°
non–profiled ω scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.968, Tmax = 0.982l = 016
2910 measured reflections2 standard reflections every 7200 min
2790 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0626P)2 + 0.1137P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2790 reflectionsΔρmax = 0.20 e Å3
184 parametersΔρmin = 0.23 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.083 (7)
Special details top

Geometry. 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.

Refinement. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.16949 (16)0.32520 (16)0.30168 (11)0.0503 (5)
O20.32915 (15)0.37168 (15)0.41691 (12)0.0518 (5)
O30.23902 (17)0.18343 (17)0.34577 (14)0.0607 (5)
O40.35178 (17)0.12149 (19)0.47936 (13)0.0697 (6)
N10.4891 (2)0.23523 (19)0.29320 (14)0.0428 (5)
N20.0194 (2)0.2716 (2)0.13398 (17)0.0504 (6)
C10.0995 (2)0.43806 (18)0.44428 (14)0.0315 (5)
C20.2069 (2)0.37309 (19)0.38263 (15)0.0349 (5)
C30.1391 (2)0.51530 (19)0.52135 (15)0.0376 (5)
H30.23290.52630.53620.045*
C40.0413 (2)0.5763 (2)0.57671 (15)0.0368 (5)
H40.07000.62750.62850.044*
C50.2453 (2)0.1282 (2)0.42708 (17)0.0432 (6)
C60.1171 (2)0.06183 (19)0.46475 (14)0.0337 (5)
C70.0122 (2)0.0890 (2)0.42851 (16)0.0395 (5)
H70.02150.14910.38020.047*
C80.1276 (2)0.0281 (2)0.53679 (15)0.0394 (5)
H80.21410.04750.56200.047*
C90.4241 (3)0.1145 (2)0.2916 (2)0.0625 (7)
H9A0.32840.12170.27130.094*
H9B0.43020.07970.35780.094*
H9C0.47150.06390.24480.094*
C100.4904 (3)0.2906 (3)0.1931 (2)0.0892 (11)
H10A0.54020.23970.14780.134*
H10B0.53500.36780.19730.134*
H10C0.39680.30060.16860.134*
C110.1256 (3)0.3116 (3)0.1309 (2)0.0654 (8)
H11A0.17040.28170.07080.098*
H11B0.12890.39800.13110.098*
H11C0.17250.28110.18890.098*
C120.0327 (4)0.1401 (3)0.1284 (2)0.0873 (11)
H12A0.01120.10420.18540.131*
H12B0.12910.11850.12870.131*
H12C0.01120.11150.06750.131*
H10.063 (3)0.302 (2)0.193 (2)0.072 (9)*
H20.069 (3)0.311 (3)0.075 (2)0.091 (10)*
H50.5818 (18)0.229 (2)0.3170 (17)0.055 (7)*
H60.441 (3)0.287 (2)0.338 (2)0.076 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0443 (9)0.0688 (11)0.0377 (9)0.0084 (8)0.0023 (7)0.0173 (8)
O20.0370 (9)0.0671 (12)0.0511 (9)0.0134 (8)0.0057 (7)0.0177 (8)
O30.0443 (10)0.0714 (13)0.0660 (11)0.0039 (9)0.0115 (8)0.0238 (10)
O40.0439 (10)0.1062 (16)0.0591 (11)0.0286 (10)0.0056 (9)0.0001 (10)
N10.0350 (10)0.0519 (13)0.0415 (11)0.0100 (9)0.0007 (8)0.0033 (9)
N20.0489 (12)0.0621 (14)0.0400 (12)0.0020 (10)0.0062 (10)0.0033 (10)
C10.0323 (10)0.0317 (11)0.0303 (10)0.0027 (9)0.0007 (8)0.0015 (9)
C20.0376 (11)0.0352 (12)0.0319 (11)0.0035 (9)0.0012 (9)0.0012 (9)
C30.0288 (10)0.0441 (13)0.0396 (12)0.0013 (9)0.0011 (9)0.0034 (10)
C40.0368 (11)0.0401 (12)0.0333 (11)0.0002 (10)0.0019 (9)0.0070 (10)
C50.0410 (13)0.0447 (13)0.0436 (13)0.0039 (10)0.0067 (11)0.0061 (11)
C60.0315 (10)0.0383 (12)0.0311 (10)0.0006 (9)0.0025 (8)0.0053 (9)
C70.0426 (13)0.0410 (13)0.0350 (11)0.0030 (10)0.0005 (9)0.0065 (10)
C80.0278 (10)0.0531 (14)0.0373 (11)0.0054 (10)0.0042 (9)0.0008 (10)
C90.0501 (15)0.0611 (18)0.0760 (18)0.0013 (13)0.0032 (13)0.0112 (14)
C100.073 (2)0.127 (3)0.0679 (19)0.022 (2)0.0125 (16)0.051 (2)
C110.0483 (15)0.086 (2)0.0621 (17)0.0076 (14)0.0070 (13)0.0018 (15)
C120.115 (3)0.074 (2)0.073 (2)0.0221 (19)0.0329 (19)0.0171 (17)
Geometric parameters (Å, º) top
O1—C21.246 (2)C5—C61.516 (3)
O2—C21.256 (2)C6—C71.378 (3)
O3—C51.244 (3)C6—C81.388 (3)
O4—C51.252 (3)C7—C8ii1.374 (3)
N1—C101.464 (3)C7—H70.9300
N1—C91.480 (3)C8—H80.9300
N1—H50.946 (16)C9—H9A0.9600
N1—H60.96 (3)C9—H9B0.9600
N2—C111.467 (3)C9—H9C0.9600
N2—C121.468 (4)C10—H10A0.9600
N2—H10.95 (3)C10—H10B0.9600
N2—H21.02 (3)C10—H10C0.9600
C1—C31.383 (3)C11—H11A0.9600
C1—C4i1.390 (3)C11—H11B0.9600
C1—C21.514 (3)C11—H11C0.9600
C3—C41.383 (3)C12—H12A0.9600
C3—H30.9300C12—H12B0.9600
C4—H40.9300C12—H12C0.9600
C10—N1—C9112.2 (2)C8ii—C7—C6120.5 (2)
C10—N1—H5108.2 (15)C8ii—C7—H7119.8
C9—N1—H5109.5 (14)C6—C7—H7119.8
C10—N1—H6109.0 (17)C7ii—C8—C6121.12 (19)
C9—N1—H6110.2 (16)C7ii—C8—H8119.4
H5—N1—H6108 (2)C6—C8—H8119.4
C11—N2—C12112.5 (2)N1—C9—H9A109.5
C11—N2—H1109.0 (17)N1—C9—H9B109.5
C12—N2—H1111.3 (16)H9A—C9—H9B109.5
C11—N2—H2107.9 (17)N1—C9—H9C109.5
C12—N2—H2110.3 (18)H9A—C9—H9C109.5
H1—N2—H2105 (2)H9B—C9—H9C109.5
C3—C1—C4i118.36 (18)N1—C10—H10A109.5
C3—C1—C2120.85 (18)N1—C10—H10B109.5
C4i—C1—C2120.77 (18)H10A—C10—H10B109.5
O1—C2—O2124.20 (19)N1—C10—H10C109.5
O1—C2—C1118.64 (18)H10A—C10—H10C109.5
O2—C2—C1117.16 (18)H10B—C10—H10C109.5
C4—C3—C1120.99 (18)N2—C11—H11A109.5
C4—C3—H3119.5N2—C11—H11B109.5
C1—C3—H3119.5H11A—C11—H11B109.5
C3—C4—C1i120.67 (18)N2—C11—H11C109.5
C3—C4—H4119.7H11A—C11—H11C109.5
C1i—C4—H4119.7H11B—C11—H11C109.5
O3—C5—O4124.3 (2)N2—C12—H12A109.5
O3—C5—C6118.3 (2)N2—C12—H12B109.5
O4—C5—C6117.4 (2)H12A—C12—H12B109.5
C7—C6—C8118.41 (19)N2—C12—H12C109.5
C7—C6—C5121.04 (19)H12A—C12—H12C109.5
C8—C6—C5120.54 (19)H12B—C12—H12C109.5
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H5···O3iii0.95 (2)1.83 (2)2.761 (3)167 (2)
N1—H6···O20.96 (3)1.78 (3)2.731 (3)171 (2)
N2—H1···O10.95 (3)1.77 (3)2.700 (3)165 (2)
N2—H2···O4iv1.02 (3)1.68 (3)2.693 (3)179 (3)
Symmetry codes: (iii) x+1, y, z; (iv) x+1/2, y+1/2, z1/2.
 

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