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The title compound, 2 C2H8N+·C12H8O42−, crystallizes as a salt in space group P21/n, the anion being located on an inversion center. The di­methyl­ammonium cations link neighboring carboxyl­ate anions via two N+—H...O hydrogen bonds [H...O = 1.72 (3) and 1.84 (3) Å, N...O = 2.671 (2) and 2.726 (2) Å, and N—H...O = 178 (3) and 173 (2)°] resulting in molecular ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017921/fl6111sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017921/fl6111Isup2.hkl
Contains datablock I

CCDC reference: 248848

Key indicators

  • Single-crystal X-ray study
  • T = 148 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H8 N
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2002) and XPREP (Bruker, 2001b); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: X-SEED; software used to prepare material for publication: X-SEED (Barbour, 2001).

Bis(dimethylammonium) 1,4-phenylenediacrylate top
Crystal data top
2C2H8N+·C12H8O42F(000) = 332
Mr = 308.38Dx = 1.195 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4922 reflections
a = 5.8270 (7) Åθ = 2.6–28.3°
b = 23.980 (3) ŵ = 0.09 mm1
c = 6.1406 (8) ÅT = 148 K
β = 92.306 (2)°Transparent block, colorless
V = 857.35 (19) Å30.36 × 0.22 × 0.18 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD
diffractometer
1556 independent reflections
Radiation source: fine-focus sealed tube1290 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 25.3°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 67
Tmin = 0.967, Tmax = 0.985k = 2828
5113 measured reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0609P)2 + 0.2787P]
where P = (Fo2 + 2Fc2)/3
1556 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
O10.1069 (2)0.12814 (7)0.5057 (3)0.0352 (4)
O20.1810 (2)0.16504 (6)0.7096 (2)0.0268 (4)
N10.3610 (3)0.18205 (7)0.7907 (3)0.0249 (4)
C10.1039 (3)0.13281 (8)0.5604 (3)0.0216 (4)
C20.2721 (3)0.09869 (8)0.4378 (3)0.0224 (4)
H20.42810.09800.48910.027*
C30.2121 (3)0.06948 (8)0.2609 (3)0.0217 (4)
H30.05530.07170.21290.026*
C40.3611 (3)0.03402 (7)0.1307 (3)0.0200 (4)
C50.2867 (3)0.01770 (8)0.0798 (3)0.0217 (4)
H50.14070.02980.13570.026*
C60.4213 (3)0.01570 (8)0.2085 (3)0.0222 (4)
H60.36600.02620.35020.027*
C70.2966 (4)0.16024 (11)1.0104 (4)0.0417 (6)
H7A0.12990.16311.03580.063*
H7B0.34320.12111.02010.063*
H7C0.37410.18211.12050.063*
C80.3124 (4)0.24188 (9)0.7659 (4)0.0379 (6)
H8A0.40660.26330.86460.057*
H8B0.34870.25320.61510.057*
H8C0.14950.24890.80150.057*
H1A0.508 (5)0.1749 (9)0.755 (4)0.031 (6)*
H1B0.270 (5)0.1621 (11)0.692 (4)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0175 (7)0.0478 (10)0.0404 (9)0.0030 (6)0.0011 (6)0.0201 (8)
O20.0193 (7)0.0302 (8)0.0311 (8)0.0013 (5)0.0020 (6)0.0094 (7)
N10.0164 (8)0.0273 (9)0.0310 (10)0.0002 (7)0.0012 (7)0.0075 (8)
C10.0187 (9)0.0241 (10)0.0222 (10)0.0020 (7)0.0022 (7)0.0010 (8)
C20.0162 (8)0.0240 (10)0.0272 (11)0.0021 (7)0.0031 (7)0.0018 (8)
C30.0164 (8)0.0217 (9)0.0274 (11)0.0004 (7)0.0039 (7)0.0004 (9)
C40.0183 (8)0.0175 (9)0.0244 (11)0.0012 (7)0.0047 (7)0.0010 (8)
C50.0179 (8)0.0202 (9)0.0270 (11)0.0021 (7)0.0012 (8)0.0004 (8)
C60.0215 (9)0.0231 (10)0.0220 (10)0.0002 (7)0.0022 (8)0.0029 (8)
C70.0318 (11)0.0521 (15)0.0416 (14)0.0010 (10)0.0057 (10)0.0101 (12)
C80.0369 (12)0.0300 (12)0.0465 (15)0.0000 (9)0.0005 (11)0.0028 (11)
Geometric parameters (Å, º) top
O1—C11.266 (2)C4—C6i1.407 (3)
O2—C11.267 (2)C5—C61.390 (3)
N1—C81.472 (3)C5—H50.9500
N1—C71.481 (3)C6—C4i1.407 (3)
N1—H1A0.89 (3)C6—H60.9500
N1—H1B0.95 (3)C7—H7A0.9800
C1—C21.502 (3)C7—H7B0.9800
C2—C31.328 (3)C7—H7C0.9800
C2—H20.9500C8—H8A0.9800
C3—C41.474 (3)C8—H8B0.9800
C3—H30.9500C8—H8C0.9800
C4—C51.402 (3)
C8—N1—C7113.31 (18)C6—C5—C4121.63 (17)
C8—N1—H1A110.4 (14)C6—C5—H5119.2
C7—N1—H1A111.1 (15)C4—C5—H5119.2
C8—N1—H1B108.1 (17)C5—C6—C4i120.53 (18)
C7—N1—H1B105.9 (16)C5—C6—H6119.7
H1A—N1—H1B108 (2)C4i—C6—H6119.7
O1—C1—O2123.94 (17)N1—C7—H7A109.5
O1—C1—C2117.68 (17)N1—C7—H7B109.5
O2—C1—C2118.37 (15)H7A—C7—H7B109.5
C3—C2—C1122.82 (16)N1—C7—H7C109.5
C3—C2—H2118.6H7A—C7—H7C109.5
C1—C2—H2118.6H7B—C7—H7C109.5
C2—C3—C4127.37 (16)N1—C8—H8A109.5
C2—C3—H3116.3N1—C8—H8B109.5
C4—C3—H3116.3H8A—C8—H8B109.5
C5—C4—C6i117.83 (17)N1—C8—H8C109.5
C5—C4—C3119.61 (16)H8A—C8—H8C109.5
C6i—C4—C3122.56 (18)H8B—C8—H8C109.5
O1—C1—C2—C38.1 (3)C2—C3—C4—C6i16.0 (3)
O2—C1—C2—C3170.85 (18)C6i—C4—C5—C60.3 (3)
C1—C2—C3—C4178.92 (18)C3—C4—C5—C6179.99 (17)
C2—C3—C4—C5163.66 (19)C4—C5—C6—C4i0.3 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O10.95 (3)1.72 (3)2.671 (2)178 (3)
N1—H1A···O2ii0.89 (3)1.84 (3)2.726 (2)173 (2)
Symmetry code: (ii) x1, y, z.
 

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