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The title compound, C2H8N+·C10H5O8, contains discrete ethyl­ammonium cations and singly deprotonated pyromellitate anions. The geometry of the ethyl­ammonium cation is not significantly different from that in other structures containing this residue. The pyromellitate anion is non-planar. The network formed by these ions is based on strong O—H...O and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026948/bh2030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026948/bh2030Isup2.hkl
Contains datablock I

CCDC reference: 618777

Key indicators

  • Single-crystal X-ray study
  • T = 102 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.028
  • wR factor = 0.085
  • Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O11 .. C19 .. 2.84 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.73 Ratio PLAT482_ALERT_4_C Small D-H..A Angle Rep for C9 .. O21 .. 99.20 Deg.
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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Ethylammonium 2,4,5-tricarboxybenzoate top
Crystal data top
C2H8N+·C10H5O8Z = 2
Mr = 299.23F(000) = 312
Triclinic, P1Dx = 1.554 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4215 (6) ÅCell parameters from 4320 reflections
b = 9.5775 (6) Åθ = 2.9–26.0°
c = 9.7259 (5) ŵ = 0.13 mm1
α = 94.830 (4)°T = 102 K
β = 94.467 (5)°Cube, colourless
γ = 110.874 (6)°0.45 × 0.42 × 0.40 mm
V = 639.31 (8) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer
2239 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.008
Graphite monochromatorθmax = 26.0°, θmin = 2.9°
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1h = 99
ω scansk = 118
4320 measured reflectionsl = 1111
2466 independent reflections
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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.085All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.1846P]
where P = (Fo2 + 2Fc2)/3
2466 reflections(Δ/σ)max < 0.001
242 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.28288 (15)0.45808 (12)0.68171 (10)0.0151 (2)
H1A0.179 (3)0.488 (2)0.6594 (19)0.043 (5)*
H1B0.292 (2)0.3976 (19)0.6056 (18)0.029 (4)*
H1C0.392 (3)0.540 (2)0.697 (2)0.042 (5)*
C20.2592 (2)0.37637 (16)0.80640 (14)0.0256 (3)
H2A0.154 (3)0.285 (2)0.777 (2)0.049 (5)*
H2B0.373 (3)0.358 (2)0.8233 (19)0.038 (5)*
C30.2235 (3)0.4694 (2)0.92620 (15)0.0352 (4)
H3A0.115 (3)0.492 (2)0.9032 (19)0.043 (5)*
H3B0.207 (3)0.418 (2)1.008 (2)0.048 (5)*
H3C0.336 (3)0.564 (3)0.953 (2)0.062 (6)*
C40.24494 (15)0.08165 (12)0.32294 (11)0.0114 (2)
C50.26023 (16)0.01747 (12)0.21253 (11)0.0128 (2)
C60.26746 (16)0.15624 (12)0.24103 (11)0.0131 (2)
H60.279 (2)0.2232 (17)0.1645 (16)0.021 (4)*
C70.26450 (15)0.19756 (12)0.37423 (11)0.0111 (2)
C80.24714 (15)0.10018 (12)0.48338 (11)0.0111 (2)
C90.23464 (15)0.03612 (12)0.45537 (12)0.0115 (2)
H90.220 (2)0.1033 (16)0.5281 (15)0.015 (3)*
C100.24551 (16)0.23945 (12)0.31545 (11)0.0122 (2)
O110.16492 (11)0.28994 (8)0.40477 (8)0.01355 (19)
O120.33228 (12)0.31556 (8)0.22343 (8)0.0169 (2)
C130.26462 (18)0.00545 (13)0.06041 (12)0.0169 (3)
O140.31725 (15)0.14007 (10)0.02393 (9)0.0246 (2)
H140.337 (3)0.216 (2)0.106 (2)0.056 (6)*
O150.22121 (15)0.10506 (10)0.02651 (9)0.0259 (2)
C160.28627 (16)0.34529 (12)0.39428 (11)0.0116 (2)
O170.12065 (11)0.46092 (9)0.36604 (8)0.01529 (19)
H170.146 (3)0.548 (2)0.3751 (19)0.042 (5)*
O180.44153 (11)0.35509 (9)0.42550 (9)0.0172 (2)
C190.24535 (15)0.14075 (12)0.62876 (11)0.0118 (2)
O200.25604 (12)0.25905 (9)0.65714 (8)0.01620 (19)
O210.23426 (12)0.03547 (9)0.72002 (8)0.01591 (19)
H210.229 (3)0.064 (2)0.806 (2)0.042 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0189 (5)0.0145 (5)0.0139 (5)0.0086 (4)0.0020 (4)0.0015 (4)
C20.0300 (7)0.0300 (7)0.0255 (7)0.0177 (6)0.0094 (6)0.0153 (6)
C30.0415 (9)0.0577 (11)0.0182 (7)0.0290 (8)0.0099 (6)0.0133 (7)
C40.0119 (5)0.0101 (5)0.0120 (5)0.0040 (4)0.0007 (4)0.0011 (4)
C50.0153 (5)0.0122 (5)0.0112 (5)0.0051 (4)0.0017 (4)0.0020 (4)
C60.0165 (5)0.0118 (5)0.0110 (5)0.0055 (4)0.0022 (4)0.0008 (4)
C70.0106 (5)0.0098 (5)0.0128 (5)0.0035 (4)0.0009 (4)0.0013 (4)
C80.0103 (5)0.0102 (5)0.0119 (5)0.0030 (4)0.0010 (4)0.0006 (4)
C90.0123 (5)0.0107 (5)0.0113 (5)0.0044 (4)0.0012 (4)0.0002 (4)
C100.0133 (5)0.0106 (5)0.0114 (5)0.0040 (4)0.0023 (4)0.0002 (4)
O110.0175 (4)0.0108 (4)0.0138 (4)0.0071 (3)0.0013 (3)0.0007 (3)
O120.0260 (5)0.0110 (4)0.0136 (4)0.0060 (3)0.0039 (3)0.0032 (3)
C130.0259 (6)0.0163 (6)0.0113 (5)0.0106 (5)0.0036 (4)0.0026 (4)
O140.0496 (6)0.0148 (4)0.0116 (4)0.0126 (4)0.0090 (4)0.0045 (3)
O150.0515 (6)0.0167 (4)0.0106 (4)0.0139 (4)0.0039 (4)0.0008 (3)
C160.0168 (6)0.0117 (5)0.0072 (5)0.0063 (4)0.0028 (4)0.0001 (4)
O170.0162 (4)0.0093 (4)0.0210 (4)0.0058 (3)0.0002 (3)0.0017 (3)
O180.0166 (4)0.0142 (4)0.0225 (4)0.0084 (3)0.0007 (3)0.0004 (3)
C190.0116 (5)0.0115 (5)0.0120 (5)0.0041 (4)0.0008 (4)0.0006 (4)
O200.0247 (4)0.0137 (4)0.0137 (4)0.0106 (3)0.0027 (3)0.0038 (3)
O210.0275 (5)0.0130 (4)0.0089 (4)0.0094 (3)0.0028 (3)0.0009 (3)
Geometric parameters (Å, º) top
N1—C21.486 (2)C7—C81.398 (2)
N1—H1A0.931 (19)C7—C161.507 (1)
N1—H1B0.923 (18)C8—C91.389 (2)
N1—H1C0.90 (2)C8—C191.4974 (15)
C2—C31.504 (2)C9—H90.955 (15)
C2—H2A0.95 (2)C10—O111.250 (1)
C2—H2B0.929 (18)C10—O121.270 (1)
C3—H3A0.92 (2)C13—O151.226 (2)
C3—H3B0.96 (2)C13—O141.296 (1)
C3—H3C0.99 (2)O14—H141.00 (2)
C4—C91.393 (2)C16—O181.2067 (15)
C4—C51.411 (2)C16—O171.319 (1)
C4—C101.518 (1)O17—H170.932 (19)
C5—C61.399 (2)C19—O201.216 (1)
C5—C131.515 (2)C19—O211.316 (1)
C6—C71.386 (2)O21—H210.90 (2)
C6—H60.970 (15)
C2—N1—H1A112.1 (11)C5—C6—H6118.0 (9)
C2—N1—H1B110.5 (10)C6—C7—C8119.26 (10)
H1A—N1—H1B107.7 (15)C6—C7—C16117.55 (9)
C2—N1—H1C109.4 (12)C8—C7—C16123.17 (9)
H1A—N1—H1C108.8 (16)C9—C8—C7118.99 (10)
H1B—N1—H1C108.3 (15)C9—C8—C19120.39 (10)
N1—C2—C3110.17 (11)C7—C8—C19120.61 (9)
N1—C2—H2A104.2 (12)C8—C9—C4122.36 (10)
C3—C2—H2A113.5 (12)C8—C9—H9120.3 (8)
N1—C2—H2B105.3 (11)C4—C9—H9117.4 (8)
C3—C2—H2B112.9 (11)O11—C10—O12123.2 (1)
H2A—C2—H2B110.0 (16)O11—C10—C4117.47 (9)
C2—C3—H3A110.5 (12)O12—C10—C4119.33 (9)
C2—C3—H3B111.3 (12)C10—O12—H14109.8 (8)
H3A—C3—H3B109.2 (16)O15—C13—O14121.0 (1)
C2—C3—H3C110.9 (13)O15—C13—C5118.8 (1)
H3A—C3—H3C108.8 (18)O14—C13—C5120.2 (1)
H3B—C3—H3C105.9 (17)C13—O14—H14110.7 (11)
C9—C4—C5118.57 (10)O18—C16—O17124.5 (1)
C9—C4—C10114.56 (9)O18—C16—C7122.7 (1)
C5—C4—C10126.83 (10)O17—C16—C7112.69 (9)
C6—C5—C4118.64 (10)C16—O17—H17108.0 (11)
C6—C5—C13113.77 (10)O20—C19—O21124.6 (1)
C4—C5—C13127.57 (10)O20—C19—C8122.2 (1)
C7—C6—C5122.11 (10)O21—C19—C8113.22 (9)
C7—C6—H6119.9 (9)C19—O21—H21111.7 (11)
C9—C4—C5—C60.98 (16)C9—C4—C10—O1127.0 (1)
C10—C4—C5—C6176.61 (10)C5—C4—C10—O11155.3 (1)
C9—C4—C5—C13177.15 (11)C9—C4—C10—O12150.6 (1)
C10—C4—C5—C135.25 (18)C5—C4—C10—O1227.1 (2)
C4—C5—C6—C71.49 (17)C6—C5—C13—O1519.6 (2)
C13—C5—C6—C7179.87 (10)C4—C5—C13—O15158.7 (1)
C5—C6—C7—C82.21 (17)C6—C5—C13—O14159.1 (1)
C5—C6—C7—C16176.05 (10)C4—C5—C13—O1422.7 (2)
C6—C7—C8—C90.44 (16)C6—C7—C16—O1892.5 (1)
C16—C7—C8—C9177.73 (10)C8—C7—C16—O1885.7 (1)
C6—C7—C8—C19179.43 (10)C6—C7—C16—O1783.7 (1)
C16—C7—C8—C191.26 (16)C8—C7—C16—O1798.1 (1)
C7—C8—C9—C42.08 (16)C9—C8—C19—O20180.0 (1)
C19—C8—C9—C4176.91 (10)C7—C8—C19—O201.0 (2)
C5—C4—C9—C82.79 (16)C9—C8—C19—O211.0 (1)
C10—C4—C9—C8175.10 (11)C7—C8—C19—O21178.00 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O121.00 (2)1.44 (2)2.426 (1)171 (2)
C6—H6···O150.97 (2)2.34 (2)2.706 (1)101 (1)
C9—H9···O110.96 (2)2.37 (1)2.735 (1)102 (1)
C9—H9···O210.96 (2)2.40 (1)2.719 (1)99.2 (9)
N1—H1B···O110.92 (2)2.11 (2)2.918 (1)146 (1)
N1—H1A···O17i0.93 (2)2.14 (2)3.005 (1)155 (2)
N1—H1A···O20ii0.93 (2)2.29 (2)2.815 (1)115 (1)
N1—H1B···O18iii0.92 (3)2.19 (2)2.800 (1)123 (1)
N1—H1C···O12iv0.90 (2)2.06 (2)2.924 (1)161 (2)
O17—H17···O11v0.93 (2)1.65 (2)2.576 (1)172 (2)
O21—H21···O15vi0.90 (2)1.71 (2)2.608 (1)176 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x+1, y+1, z+1; (v) x, y1, z; (vi) x, y, z+1.
 

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