Ethyl­ammonium 2,4,5-tricarboxy­benzoate

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.

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

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Computing details

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

Crystal data

C2H8N^+·C10H5O8^−	Z = 2
Mr = 299.23	F(000) = 312
Triclinic, P1	Dx = 1.554 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4215 (6) Å	Cell parameters from 4320 reflections
b = 9.5775 (6) Å	θ = 2.9–26.0°
c = 9.7259 (5) Å	µ = 0.13 mm^−1
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) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer	2239 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.008
Graphite monochromator	θmax = 26.0°, θmin = 2.9°
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	h = −9→9
ω scans	k = −11→8
4320 measured reflections	l = −11→11
2466 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: difference Fourier map
wR(F^2) = 0.085	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.1846P] where P = (Fo^2 + 2Fc^2)/3
2466 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.28288 (15)	0.45808 (12)	0.68171 (10)	0.0151 (2)
H1A	0.179 (3)	0.488 (2)	0.6594 (19)	0.043 (5)*
H1B	0.292 (2)	0.3976 (19)	0.6056 (18)	0.029 (4)*
H1C	0.392 (3)	0.540 (2)	0.697 (2)	0.042 (5)*
C2	0.2592 (2)	0.37637 (16)	0.80640 (14)	0.0256 (3)
H2A	0.154 (3)	0.285 (2)	0.777 (2)	0.049 (5)*
H2B	0.373 (3)	0.358 (2)	0.8233 (19)	0.038 (5)*
C3	0.2235 (3)	0.4694 (2)	0.92620 (15)	0.0352 (4)
H3A	0.115 (3)	0.492 (2)	0.9032 (19)	0.043 (5)*
H3B	0.207 (3)	0.418 (2)	1.008 (2)	0.048 (5)*
H3C	0.336 (3)	0.564 (3)	0.953 (2)	0.062 (6)*
C4	0.24494 (15)	0.08165 (12)	0.32294 (11)	0.0114 (2)
C5	0.26023 (16)	−0.01747 (12)	0.21253 (11)	0.0128 (2)
C6	0.26746 (16)	−0.15624 (12)	0.24103 (11)	0.0131 (2)
H6	0.279 (2)	−0.2232 (17)	0.1645 (16)	0.021 (4)*
C7	0.26450 (15)	−0.19756 (12)	0.37423 (11)	0.0111 (2)
C8	0.24714 (15)	−0.10018 (12)	0.48338 (11)	0.0111 (2)
C9	0.23464 (15)	0.03612 (12)	0.45537 (12)	0.0115 (2)
H9	0.220 (2)	0.1033 (16)	0.5281 (15)	0.015 (3)*
C10	0.24551 (16)	0.23945 (12)	0.31545 (11)	0.0122 (2)
O11	0.16492 (11)	0.28994 (8)	0.40477 (8)	0.01355 (19)
O12	0.33228 (12)	0.31556 (8)	0.22343 (8)	0.0169 (2)
C13	0.26462 (18)	0.00545 (13)	0.06041 (12)	0.0169 (3)
O14	0.31725 (15)	0.14007 (10)	0.02393 (9)	0.0246 (2)
H14	0.337 (3)	0.216 (2)	0.106 (2)	0.056 (6)*
O15	0.22121 (15)	−0.10506 (10)	−0.02651 (9)	0.0259 (2)
C16	0.28627 (16)	−0.34529 (12)	0.39428 (11)	0.0116 (2)
O17	0.12065 (11)	−0.46092 (9)	0.36604 (8)	0.01529 (19)
H17	0.146 (3)	−0.548 (2)	0.3751 (19)	0.042 (5)*
O18	0.44153 (11)	−0.35509 (9)	0.42550 (9)	0.0172 (2)
C19	0.24535 (15)	−0.14075 (12)	0.62876 (11)	0.0118 (2)
O20	0.25604 (12)	−0.25905 (9)	0.65714 (8)	0.01620 (19)
O21	0.23426 (12)	−0.03547 (9)	0.72002 (8)	0.01591 (19)
H21	0.229 (3)	−0.064 (2)	0.806 (2)	0.042 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0189 (5)	0.0145 (5)	0.0139 (5)	0.0086 (4)	0.0020 (4)	0.0015 (4)
C2	0.0300 (7)	0.0300 (7)	0.0255 (7)	0.0177 (6)	0.0094 (6)	0.0153 (6)
C3	0.0415 (9)	0.0577 (11)	0.0182 (7)	0.0290 (8)	0.0099 (6)	0.0133 (7)
C4	0.0119 (5)	0.0101 (5)	0.0120 (5)	0.0040 (4)	0.0007 (4)	0.0011 (4)
C5	0.0153 (5)	0.0122 (5)	0.0112 (5)	0.0051 (4)	0.0017 (4)	0.0020 (4)
C6	0.0165 (5)	0.0118 (5)	0.0110 (5)	0.0055 (4)	0.0022 (4)	−0.0008 (4)
C7	0.0106 (5)	0.0098 (5)	0.0128 (5)	0.0035 (4)	0.0009 (4)	0.0013 (4)
C8	0.0103 (5)	0.0102 (5)	0.0119 (5)	0.0030 (4)	0.0010 (4)	0.0006 (4)
C9	0.0123 (5)	0.0107 (5)	0.0113 (5)	0.0044 (4)	0.0012 (4)	−0.0002 (4)
C10	0.0133 (5)	0.0106 (5)	0.0114 (5)	0.0040 (4)	−0.0023 (4)	0.0002 (4)
O11	0.0175 (4)	0.0108 (4)	0.0138 (4)	0.0071 (3)	0.0013 (3)	0.0007 (3)
O12	0.0260 (5)	0.0110 (4)	0.0136 (4)	0.0060 (3)	0.0039 (3)	0.0032 (3)
C13	0.0259 (6)	0.0163 (6)	0.0113 (5)	0.0106 (5)	0.0036 (4)	0.0026 (4)
O14	0.0496 (6)	0.0148 (4)	0.0116 (4)	0.0126 (4)	0.0090 (4)	0.0045 (3)
O15	0.0515 (6)	0.0167 (4)	0.0106 (4)	0.0139 (4)	0.0039 (4)	0.0008 (3)
C16	0.0168 (6)	0.0117 (5)	0.0072 (5)	0.0063 (4)	0.0028 (4)	−0.0001 (4)
O17	0.0162 (4)	0.0093 (4)	0.0210 (4)	0.0058 (3)	−0.0002 (3)	0.0017 (3)
O18	0.0166 (4)	0.0142 (4)	0.0225 (4)	0.0084 (3)	0.0007 (3)	0.0004 (3)
C19	0.0116 (5)	0.0115 (5)	0.0120 (5)	0.0041 (4)	0.0008 (4)	0.0006 (4)
O20	0.0247 (4)	0.0137 (4)	0.0137 (4)	0.0106 (3)	0.0027 (3)	0.0038 (3)
O21	0.0275 (5)	0.0130 (4)	0.0089 (4)	0.0094 (3)	0.0028 (3)	0.0009 (3)

Geometric parameters (Å, º)

N1—C2	1.486 (2)	C7—C8	1.398 (2)
N1—H1A	0.931 (19)	C7—C16	1.507 (1)
N1—H1B	0.923 (18)	C8—C9	1.389 (2)
N1—H1C	0.90 (2)	C8—C19	1.4974 (15)
C2—C3	1.504 (2)	C9—H9	0.955 (15)
C2—H2A	0.95 (2)	C10—O11	1.250 (1)
C2—H2B	0.929 (18)	C10—O12	1.270 (1)
C3—H3A	0.92 (2)	C13—O15	1.226 (2)
C3—H3B	0.96 (2)	C13—O14	1.296 (1)
C3—H3C	0.99 (2)	O14—H14	1.00 (2)
C4—C9	1.393 (2)	C16—O18	1.2067 (15)
C4—C5	1.411 (2)	C16—O17	1.319 (1)
C4—C10	1.518 (1)	O17—H17	0.932 (19)
C5—C6	1.399 (2)	C19—O20	1.216 (1)
C5—C13	1.515 (2)	C19—O21	1.316 (1)
C6—C7	1.386 (2)	O21—H21	0.90 (2)
C6—H6	0.970 (15)
C2—N1—H1A	112.1 (11)	C5—C6—H6	118.0 (9)
C2—N1—H1B	110.5 (10)	C6—C7—C8	119.26 (10)
H1A—N1—H1B	107.7 (15)	C6—C7—C16	117.55 (9)
C2—N1—H1C	109.4 (12)	C8—C7—C16	123.17 (9)
H1A—N1—H1C	108.8 (16)	C9—C8—C7	118.99 (10)
H1B—N1—H1C	108.3 (15)	C9—C8—C19	120.39 (10)
N1—C2—C3	110.17 (11)	C7—C8—C19	120.61 (9)
N1—C2—H2A	104.2 (12)	C8—C9—C4	122.36 (10)
C3—C2—H2A	113.5 (12)	C8—C9—H9	120.3 (8)
N1—C2—H2B	105.3 (11)	C4—C9—H9	117.4 (8)
C3—C2—H2B	112.9 (11)	O11—C10—O12	123.2 (1)
H2A—C2—H2B	110.0 (16)	O11—C10—C4	117.47 (9)
C2—C3—H3A	110.5 (12)	O12—C10—C4	119.33 (9)
C2—C3—H3B	111.3 (12)	C10—O12—H14	109.8 (8)
H3A—C3—H3B	109.2 (16)	O15—C13—O14	121.0 (1)
C2—C3—H3C	110.9 (13)	O15—C13—C5	118.8 (1)
H3A—C3—H3C	108.8 (18)	O14—C13—C5	120.2 (1)
H3B—C3—H3C	105.9 (17)	C13—O14—H14	110.7 (11)
C9—C4—C5	118.57 (10)	O18—C16—O17	124.5 (1)
C9—C4—C10	114.56 (9)	O18—C16—C7	122.7 (1)
C5—C4—C10	126.83 (10)	O17—C16—C7	112.69 (9)
C6—C5—C4	118.64 (10)	C16—O17—H17	108.0 (11)
C6—C5—C13	113.77 (10)	O20—C19—O21	124.6 (1)
C4—C5—C13	127.57 (10)	O20—C19—C8	122.2 (1)
C7—C6—C5	122.11 (10)	O21—C19—C8	113.22 (9)
C7—C6—H6	119.9 (9)	C19—O21—H21	111.7 (11)
C9—C4—C5—C6	−0.98 (16)	C9—C4—C10—O11	−27.0 (1)
C10—C4—C5—C6	176.61 (10)	C5—C4—C10—O11	155.3 (1)
C9—C4—C5—C13	177.15 (11)	C9—C4—C10—O12	150.6 (1)
C10—C4—C5—C13	−5.25 (18)	C5—C4—C10—O12	−27.1 (2)
C4—C5—C6—C7	−1.49 (17)	C6—C5—C13—O15	19.6 (2)
C13—C5—C6—C7	−179.87 (10)	C4—C5—C13—O15	−158.7 (1)
C5—C6—C7—C8	2.21 (17)	C6—C5—C13—O14	−159.1 (1)
C5—C6—C7—C16	−176.05 (10)	C4—C5—C13—O14	22.7 (2)
C6—C7—C8—C9	−0.44 (16)	C6—C7—C16—O18	92.5 (1)
C16—C7—C8—C9	177.73 (10)	C8—C7—C16—O18	−85.7 (1)
C6—C7—C8—C19	−179.43 (10)	C6—C7—C16—O17	−83.7 (1)
C16—C7—C8—C19	−1.26 (16)	C8—C7—C16—O17	98.1 (1)
C7—C8—C9—C4	−2.08 (16)	C9—C8—C19—O20	180.0 (1)
C19—C8—C9—C4	176.91 (10)	C7—C8—C19—O20	−1.0 (2)
C5—C4—C9—C8	2.79 (16)	C9—C8—C19—O21	−1.0 (1)
C10—C4—C9—C8	−175.10 (11)	C7—C8—C19—O21	178.00 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O12	1.00 (2)	1.44 (2)	2.426 (1)	171 (2)
C6—H6···O15	0.97 (2)	2.34 (2)	2.706 (1)	101 (1)
C9—H9···O11	0.96 (2)	2.37 (1)	2.735 (1)	102 (1)
C9—H9···O21	0.96 (2)	2.40 (1)	2.719 (1)	99.2 (9)
N1—H1B···O11	0.92 (2)	2.11 (2)	2.918 (1)	146 (1)
N1—H1A···O17^i	0.93 (2)	2.14 (2)	3.005 (1)	155 (2)
N1—H1A···O20^ii	0.93 (2)	2.29 (2)	2.815 (1)	115 (1)
N1—H1B···O18^iii	0.92 (3)	2.19 (2)	2.800 (1)	123 (1)
N1—H1C···O12^iv	0.90 (2)	2.06 (2)	2.924 (1)	161 (2)
O17—H17···O11^v	0.93 (2)	1.65 (2)	2.576 (1)	172 (2)
O21—H21···O15^vi	0.90 (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, y−1, z; (vi) x, y, z+1.