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The anions in the title compound, 4NH4+·C10H2O84-·4H2O, are held together by regular hydrogen bonds from the carboxyl­ate O atoms to the ammonium cations and water mol­ecules, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015687/qa0416sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015687/qa0416Isup2.hkl
Contains datablock I

CCDC reference: 156218

Comment top

NO COMMENT

Experimental top

The title compound was prepared by reacting benzene- 1,2,4,5-tetracarboxylic acid (2.0 g, 8 mmol, Aldrich) and concentrated aqueous ammonia (250 ml, 14.8 N, Aldrich) in a 250 ml beaker. The mixture was stirred and the volume was concentrated to 10 ml by the application of heat. Crystals were obtained by allowing the complete evaporation of liquid from this mixture at room temperature over a period of several weeks.

Refinement top

The space group (monoclinic P) was chosen based on the fact that a data set collected in an orthorhombic setting did not produce a reasonable solution. The C—H, O—H, N—H and Uiso values for the refined H atoms are in the ranges 0.95 (2), 0.85 (4)–0.91 (5), 0.84 (5)–1.00 (4) Å and 0.020 (5)–0.140 (19) Å2, respectively.

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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
4NH4+·C10H2O84·4H2OF(000) = 420
Mr = 394.34Dx = 1.464 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 6.5590 (11) ÅCell parameters from 25 reflections
b = 23.134 (5) Åθ = 10–15°
c = 6.7460 (12) ŵ = 0.13 mm1
β = 119.071 (15)°T = 293 K
V = 894.7 (3) Å3Prism, pale yellow
Z = 20.40 × 0.25 × 0.18 mm
Data collection top
Enraf Nonius TurboCAD-4
diffractometer
Rint = 0.046
non–profiled ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: ψ scan
(North et al., 1968)
h = 07
Tmin = 0.899, Tmax = 0.980k = 027
1695 measured reflectionsl = 87
1560 independent reflections3 standard reflections every 166 min
1169 reflections with I > 2σ(I) intensity decay: 7%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.2097P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.20 e Å3
1560 reflectionsΔρmin = 0.19 e Å3
170 parameters
Crystal data top
4NH4+·C10H2O84·4H2OV = 894.7 (3) Å3
Mr = 394.34Z = 2
Monoclinic, P21/nMo Kα radiation
a = 6.5590 (11) ŵ = 0.13 mm1
b = 23.134 (5) ÅT = 293 K
c = 6.7460 (12) Å0.40 × 0.25 × 0.18 mm
β = 119.071 (15)°
Data collection top
Enraf Nonius TurboCAD-4
diffractometer
1169 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.046
Tmin = 0.899, Tmax = 0.9803 standard reflections every 166 min
1695 measured reflections intensity decay: 7%
1560 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.104All H-atom parameters refined
S = 1.07Δρmax = 0.20 e Å3
1560 reflectionsΔρmin = 0.19 e Å3
170 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.1805 (3)0.10106 (6)0.6727 (3)0.0395 (4)
O120.1771 (3)0.01462 (6)0.8135 (3)0.0387 (4)
O510.3712 (3)0.14777 (6)0.2808 (2)0.0344 (4)
O520.6432 (3)0.15297 (6)0.6420 (2)0.0330 (4)
C10.2344 (3)0.04832 (8)0.7041 (3)0.0259 (5)
C20.3765 (3)0.02398 (8)0.6019 (3)0.0215 (4)
C30.3915 (3)0.03554 (8)0.5839 (3)0.0231 (4)
C40.5125 (3)0.06009 (8)0.4836 (3)0.0200 (4)
C50.5114 (3)0.12524 (8)0.4662 (3)0.0227 (4)
O10.5406 (3)0.27092 (8)0.5390 (3)0.0502 (5)
O20.1003 (4)0.18573 (10)0.6593 (4)0.0594 (6)
N10.6007 (5)0.19466 (10)1.0217 (4)0.0459 (6)
N20.0121 (4)0.07855 (8)0.9648 (3)0.0294 (4)
H310.315 (4)0.0601 (8)0.640 (3)0.020 (5)*
H10.580 (6)0.2337 (15)0.570 (6)0.080 (10)*
H20.658 (6)0.2897 (13)0.650 (5)0.062 (9)*
H30.022 (7)0.1593 (16)0.565 (7)0.088 (13)*
H40.025 (9)0.1927 (19)0.740 (9)0.140 (19)*
H110.584 (7)0.2334 (18)1.072 (7)0.106 (13)*
H120.655 (8)0.1623 (17)1.134 (7)0.118 (14)*
H130.711 (8)0.2032 (18)0.997 (8)0.114 (16)*
H140.469 (9)0.1830 (17)0.890 (8)0.118 (16)*
H210.137 (5)0.1018 (10)1.072 (4)0.044 (7)*
H220.102 (4)0.1022 (10)0.856 (4)0.034 (6)*
H230.059 (5)0.0531 (12)0.893 (4)0.053 (8)*
H240.053 (5)0.0573 (12)1.046 (5)0.067 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0467 (10)0.0235 (8)0.0631 (11)0.0049 (7)0.0383 (9)0.0010 (7)
O120.0506 (10)0.0340 (9)0.0513 (10)0.0017 (7)0.0404 (9)0.0038 (7)
O510.0349 (9)0.0227 (7)0.0334 (8)0.0018 (6)0.0071 (7)0.0048 (6)
O520.0391 (9)0.0227 (7)0.0299 (8)0.0049 (6)0.0109 (7)0.0039 (6)
C10.0243 (10)0.0251 (11)0.0299 (11)0.0024 (8)0.0144 (9)0.0035 (8)
C20.0206 (9)0.0218 (9)0.0214 (9)0.0004 (8)0.0096 (8)0.0004 (8)
C30.0232 (10)0.0207 (10)0.0272 (10)0.0023 (8)0.0138 (9)0.0017 (8)
C40.0176 (9)0.0202 (9)0.0201 (9)0.0010 (8)0.0074 (8)0.0000 (8)
C50.0217 (10)0.0202 (10)0.0288 (11)0.0003 (8)0.0142 (9)0.0000 (8)
O10.0424 (11)0.0285 (9)0.0587 (12)0.0029 (8)0.0080 (10)0.0004 (8)
O20.0516 (12)0.0563 (13)0.0663 (14)0.0114 (10)0.0253 (12)0.0026 (11)
N10.0584 (15)0.0396 (12)0.0478 (14)0.0013 (11)0.0321 (13)0.0027 (11)
N20.0322 (10)0.0274 (10)0.0298 (10)0.0007 (9)0.0159 (9)0.0011 (9)
Geometric parameters (Å, º) top
O11—C11.259 (2)O1—H20.88 (3)
O12—C11.251 (2)O2—H30.85 (4)
O51—C51.251 (2)O2—H40.91 (5)
O52—C51.252 (2)N1—H110.98 (4)
C1—C21.511 (3)N1—H121.00 (4)
C2—C31.390 (3)N1—H130.84 (5)
C2—C4i1.404 (3)N1—H140.93 (5)
C3—C41.390 (3)N2—H210.95 (3)
C3—H310.95 (2)N2—H220.93 (3)
C4—C2i1.404 (3)N2—H230.91 (3)
C4—C51.511 (3)N2—H240.98 (3)
O1—H10.89 (3)
O12—C1—O11124.25 (18)H1—O1—H2104 (3)
O12—C1—C2117.75 (17)H3—O2—H4106 (4)
O11—C1—C2118.00 (17)H11—N1—H12119 (3)
C3—C2—C4i118.73 (17)H11—N1—H1396 (4)
C3—C2—C1119.65 (17)H12—N1—H13108 (4)
C4i—C2—C1121.58 (17)H11—N1—H14113 (4)
C4—C3—C2121.94 (18)H12—N1—H14109 (4)
C4—C3—H31119.3 (12)H13—N1—H14112 (4)
C2—C3—H31118.8 (12)H21—N2—H22109 (2)
C3—C4—C2i119.33 (17)H21—N2—H23112 (2)
C3—C4—C5117.59 (16)H22—N2—H23108 (2)
C2i—C4—C5123.05 (17)H21—N2—H24108 (2)
O51—C5—O52124.56 (17)H22—N2—H24110 (2)
O51—C5—C4117.81 (17)H23—N2—H24109 (2)
O52—C5—C4117.54 (17)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O510.89 (3)2.65 (3)3.241 (2)124 (3)
O1—H1···O520.89 (3)1.92 (4)2.816 (2)175 (3)
O1—H2···O51ii0.88 (3)1.91 (3)2.732 (2)155 (3)
O2—H4···O1iii0.91 (5)2.14 (5)2.948 (3)147 (4)
O2—H3···O11iv0.85 (4)2.02 (4)2.870 (3)176 (4)
O2—H4···O52v0.91 (5)2.44 (5)3.039 (3)124 (4)
N1—H13···O10.84 (5)3.15 (4)3.554 (3)113 (3)
N1—H11···O2ii0.98 (4)1.95 (4)2.919 (3)169 (4)
N1—H12···O11vi1.00 (4)1.87 (4)2.850 (3)165 (4)
N1—H13···O1ii0.84 (5)2.13 (5)2.941 (3)163 (4)
N1—H14···O20.93 (5)2.15 (5)2.999 (4)152 (4)
N2—H22···O20.93 (3)2.99 (2)3.448 (3)111.9 (16)
N2—H23···O120.91 (3)1.93 (3)2.816 (2)164 (2)
N2—H21···O51vii0.95 (3)1.84 (3)2.788 (3)178 (2)
N2—H22···O52v0.93 (3)1.98 (3)2.905 (3)175 (2)
N2—H24···O11viii0.98 (3)2.62 (3)3.293 (3)126 (2)
N2—H24···O12viii0.98 (3)1.81 (3)2.787 (2)177 (3)
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z+1/2; (iv) x, y, z+1; (v) x1, y, z; (vi) x+1, y, z+2; (vii) x, y, z+1; (viii) x, y, z+2.

Experimental details

Crystal data
Chemical formula4NH4+·C10H2O84·4H2O
Mr394.34
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)6.5590 (11), 23.134 (5), 6.7460 (12)
β (°) 119.071 (15)
V3)894.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.40 × 0.25 × 0.18
Data collection
DiffractometerEnraf Nonius TurboCAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.899, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
1695, 1560, 1169
Rint0.046
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.104, 1.07
No. of reflections1560
No. of parameters170
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.20, 0.19

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O510.89 (3)2.65 (3)3.241 (2)124 (3)
O1—H1···O520.89 (3)1.92 (4)2.816 (2)175 (3)
O1—H2···O51i0.88 (3)1.91 (3)2.732 (2)155 (3)
O2—H4···O1ii0.91 (5)2.14 (5)2.948 (3)147 (4)
O2—H3···O11iii0.85 (4)2.02 (4)2.870 (3)176 (4)
O2—H4···O52iv0.91 (5)2.44 (5)3.039 (3)124 (4)
N1—H13···O10.84 (5)3.15 (4)3.554 (3)113 (3)
N1—H11···O2i0.98 (4)1.95 (4)2.919 (3)169 (4)
N1—H12···O11v1.00 (4)1.87 (4)2.850 (3)165 (4)
N1—H13···O1i0.84 (5)2.13 (5)2.941 (3)163 (4)
N1—H14···O20.93 (5)2.15 (5)2.999 (4)152 (4)
N2—H22···O20.93 (3)2.99 (2)3.448 (3)111.9 (16)
N2—H23···O120.91 (3)1.93 (3)2.816 (2)164 (2)
N2—H21···O51vi0.95 (3)1.84 (3)2.788 (3)178 (2)
N2—H22···O52iv0.93 (3)1.98 (3)2.905 (3)175 (2)
N2—H24···O11vii0.98 (3)2.62 (3)3.293 (3)126 (2)
N2—H24···O12vii0.98 (3)1.81 (3)2.787 (2)177 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x, y, z+1; (iv) x1, y, z; (v) x+1, y, z+2; (vi) x, y, z+1; (vii) x, y, z+2.
 

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