Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015687/qa0416sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015687/qa0416Isup2.hkl |
CCDC reference: 156218
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.
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.
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).
4NH4+·C10H2O84−·4H2O | F(000) = 420 |
Mr = 394.34 | Dx = 1.464 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
a = 6.5590 (11) Å | Cell parameters from 25 reflections |
b = 23.134 (5) Å | θ = 10–15° |
c = 6.7460 (12) Å | µ = 0.13 mm−1 |
β = 119.071 (15)° | T = 293 K |
V = 894.7 (3) Å3 | Prism, pale yellow |
Z = 2 | 0.40 × 0.25 × 0.18 mm |
Enraf Nonius TurboCAD-4 diffractometer | Rint = 0.046 |
non–profiled ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→7 |
Tmin = 0.899, Tmax = 0.980 | k = 0→27 |
1695 measured reflections | l = −8→7 |
1560 independent reflections | 3 standard reflections every 166 min |
1169 reflections with I > 2σ(I) | intensity decay: 7% |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All 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 = 1.07 | Δρmax = 0.20 e Å−3 |
1560 reflections | Δρmin = −0.19 e Å−3 |
170 parameters |
4NH4+·C10H2O84−·4H2O | V = 894.7 (3) Å3 |
Mr = 394.34 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.5590 (11) Å | µ = 0.13 mm−1 |
b = 23.134 (5) Å | T = 293 K |
c = 6.7460 (12) Å | 0.40 × 0.25 × 0.18 mm |
β = 119.071 (15)° |
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 = 0.980 | 3 standard reflections every 166 min |
1695 measured reflections | intensity decay: 7% |
1560 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.20 e Å−3 |
1560 reflections | Δρmin = −0.19 e Å−3 |
170 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.1805 (3) | −0.10106 (6) | 0.6727 (3) | 0.0395 (4) | |
O12 | 0.1771 (3) | −0.01462 (6) | 0.8135 (3) | 0.0387 (4) | |
O51 | 0.3712 (3) | 0.14777 (6) | 0.2808 (2) | 0.0344 (4) | |
O52 | 0.6432 (3) | 0.15297 (6) | 0.6420 (2) | 0.0330 (4) | |
C1 | 0.2344 (3) | −0.04832 (8) | 0.7041 (3) | 0.0259 (5) | |
C2 | 0.3765 (3) | −0.02398 (8) | 0.6019 (3) | 0.0215 (4) | |
C3 | 0.3915 (3) | 0.03554 (8) | 0.5839 (3) | 0.0231 (4) | |
C4 | 0.5125 (3) | 0.06009 (8) | 0.4836 (3) | 0.0200 (4) | |
C5 | 0.5114 (3) | 0.12524 (8) | 0.4662 (3) | 0.0227 (4) | |
O1 | 0.5406 (3) | 0.27092 (8) | 0.5390 (3) | 0.0502 (5) | |
O2 | 0.1003 (4) | 0.18573 (10) | 0.6593 (4) | 0.0594 (6) | |
N1 | 0.6007 (5) | 0.19466 (10) | 1.0217 (4) | 0.0459 (6) | |
N2 | 0.0121 (4) | 0.07855 (8) | 0.9648 (3) | 0.0294 (4) | |
H31 | 0.315 (4) | 0.0601 (8) | 0.640 (3) | 0.020 (5)* | |
H1 | 0.580 (6) | 0.2337 (15) | 0.570 (6) | 0.080 (10)* | |
H2 | 0.658 (6) | 0.2897 (13) | 0.650 (5) | 0.062 (9)* | |
H3 | 0.022 (7) | 0.1593 (16) | 0.565 (7) | 0.088 (13)* | |
H4 | 0.025 (9) | 0.1927 (19) | 0.740 (9) | 0.140 (19)* | |
H11 | 0.584 (7) | 0.2334 (18) | 1.072 (7) | 0.106 (13)* | |
H12 | 0.655 (8) | 0.1623 (17) | 1.134 (7) | 0.118 (14)* | |
H13 | 0.711 (8) | 0.2032 (18) | 0.997 (8) | 0.114 (16)* | |
H14 | 0.469 (9) | 0.1830 (17) | 0.890 (8) | 0.118 (16)* | |
H21 | 0.137 (5) | 0.1018 (10) | 1.072 (4) | 0.044 (7)* | |
H22 | −0.102 (4) | 0.1022 (10) | 0.856 (4) | 0.034 (6)* | |
H23 | 0.059 (5) | 0.0531 (12) | 0.893 (4) | 0.053 (8)* | |
H24 | −0.053 (5) | 0.0573 (12) | 1.046 (5) | 0.067 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0467 (10) | 0.0235 (8) | 0.0631 (11) | −0.0049 (7) | 0.0383 (9) | 0.0010 (7) |
O12 | 0.0506 (10) | 0.0340 (9) | 0.0513 (10) | −0.0017 (7) | 0.0404 (9) | −0.0038 (7) |
O51 | 0.0349 (9) | 0.0227 (7) | 0.0334 (8) | 0.0018 (6) | 0.0071 (7) | 0.0048 (6) |
O52 | 0.0391 (9) | 0.0227 (7) | 0.0299 (8) | −0.0049 (6) | 0.0109 (7) | −0.0039 (6) |
C1 | 0.0243 (10) | 0.0251 (11) | 0.0299 (11) | 0.0024 (8) | 0.0144 (9) | 0.0035 (8) |
C2 | 0.0206 (9) | 0.0218 (9) | 0.0214 (9) | −0.0004 (8) | 0.0096 (8) | 0.0004 (8) |
C3 | 0.0232 (10) | 0.0207 (10) | 0.0272 (10) | 0.0023 (8) | 0.0138 (9) | −0.0017 (8) |
C4 | 0.0176 (9) | 0.0202 (9) | 0.0201 (9) | 0.0010 (8) | 0.0074 (8) | 0.0000 (8) |
C5 | 0.0217 (10) | 0.0202 (10) | 0.0288 (11) | 0.0003 (8) | 0.0142 (9) | 0.0000 (8) |
O1 | 0.0424 (11) | 0.0285 (9) | 0.0587 (12) | −0.0029 (8) | 0.0080 (10) | −0.0004 (8) |
O2 | 0.0516 (12) | 0.0563 (13) | 0.0663 (14) | −0.0114 (10) | 0.0253 (12) | 0.0026 (11) |
N1 | 0.0584 (15) | 0.0396 (12) | 0.0478 (14) | 0.0013 (11) | 0.0321 (13) | 0.0027 (11) |
N2 | 0.0322 (10) | 0.0274 (10) | 0.0298 (10) | −0.0007 (9) | 0.0159 (9) | −0.0011 (9) |
O11—C1 | 1.259 (2) | O1—H2 | 0.88 (3) |
O12—C1 | 1.251 (2) | O2—H3 | 0.85 (4) |
O51—C5 | 1.251 (2) | O2—H4 | 0.91 (5) |
O52—C5 | 1.252 (2) | N1—H11 | 0.98 (4) |
C1—C2 | 1.511 (3) | N1—H12 | 1.00 (4) |
C2—C3 | 1.390 (3) | N1—H13 | 0.84 (5) |
C2—C4i | 1.404 (3) | N1—H14 | 0.93 (5) |
C3—C4 | 1.390 (3) | N2—H21 | 0.95 (3) |
C3—H31 | 0.95 (2) | N2—H22 | 0.93 (3) |
C4—C2i | 1.404 (3) | N2—H23 | 0.91 (3) |
C4—C5 | 1.511 (3) | N2—H24 | 0.98 (3) |
O1—H1 | 0.89 (3) | ||
O12—C1—O11 | 124.25 (18) | H1—O1—H2 | 104 (3) |
O12—C1—C2 | 117.75 (17) | H3—O2—H4 | 106 (4) |
O11—C1—C2 | 118.00 (17) | H11—N1—H12 | 119 (3) |
C3—C2—C4i | 118.73 (17) | H11—N1—H13 | 96 (4) |
C3—C2—C1 | 119.65 (17) | H12—N1—H13 | 108 (4) |
C4i—C2—C1 | 121.58 (17) | H11—N1—H14 | 113 (4) |
C4—C3—C2 | 121.94 (18) | H12—N1—H14 | 109 (4) |
C4—C3—H31 | 119.3 (12) | H13—N1—H14 | 112 (4) |
C2—C3—H31 | 118.8 (12) | H21—N2—H22 | 109 (2) |
C3—C4—C2i | 119.33 (17) | H21—N2—H23 | 112 (2) |
C3—C4—C5 | 117.59 (16) | H22—N2—H23 | 108 (2) |
C2i—C4—C5 | 123.05 (17) | H21—N2—H24 | 108 (2) |
O51—C5—O52 | 124.56 (17) | H22—N2—H24 | 110 (2) |
O51—C5—C4 | 117.81 (17) | H23—N2—H24 | 109 (2) |
O52—C5—C4 | 117.54 (17) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O51 | 0.89 (3) | 2.65 (3) | 3.241 (2) | 124 (3) |
O1—H1···O52 | 0.89 (3) | 1.92 (4) | 2.816 (2) | 175 (3) |
O1—H2···O51ii | 0.88 (3) | 1.91 (3) | 2.732 (2) | 155 (3) |
O2—H4···O1iii | 0.91 (5) | 2.14 (5) | 2.948 (3) | 147 (4) |
O2—H3···O11iv | 0.85 (4) | 2.02 (4) | 2.870 (3) | 176 (4) |
O2—H4···O52v | 0.91 (5) | 2.44 (5) | 3.039 (3) | 124 (4) |
N1—H13···O1 | 0.84 (5) | 3.15 (4) | 3.554 (3) | 113 (3) |
N1—H11···O2ii | 0.98 (4) | 1.95 (4) | 2.919 (3) | 169 (4) |
N1—H12···O11vi | 1.00 (4) | 1.87 (4) | 2.850 (3) | 165 (4) |
N1—H13···O1ii | 0.84 (5) | 2.13 (5) | 2.941 (3) | 163 (4) |
N1—H14···O2 | 0.93 (5) | 2.15 (5) | 2.999 (4) | 152 (4) |
N2—H22···O2 | 0.93 (3) | 2.99 (2) | 3.448 (3) | 111.9 (16) |
N2—H23···O12 | 0.91 (3) | 1.93 (3) | 2.816 (2) | 164 (2) |
N2—H21···O51vii | 0.95 (3) | 1.84 (3) | 2.788 (3) | 178 (2) |
N2—H22···O52v | 0.93 (3) | 1.98 (3) | 2.905 (3) | 175 (2) |
N2—H24···O11viii | 0.98 (3) | 2.62 (3) | 3.293 (3) | 126 (2) |
N2—H24···O12viii | 0.98 (3) | 1.81 (3) | 2.787 (2) | 177 (3) |
Symmetry codes: (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x, −y, −z+1; (v) x−1, y, z; (vi) −x+1, −y, −z+2; (vii) x, y, z+1; (viii) −x, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | 4NH4+·C10H2O84−·4H2O |
Mr | 394.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.5590 (11), 23.134 (5), 6.7460 (12) |
β (°) | 119.071 (15) |
V (Å3) | 894.7 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.40 × 0.25 × 0.18 |
Data collection | |
Diffractometer | Enraf Nonius TurboCAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.899, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1695, 1560, 1169 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.104, 1.07 |
No. of reflections | 1560 |
No. of parameters | 170 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O51 | 0.89 (3) | 2.65 (3) | 3.241 (2) | 124 (3) |
O1—H1···O52 | 0.89 (3) | 1.92 (4) | 2.816 (2) | 175 (3) |
O1—H2···O51i | 0.88 (3) | 1.91 (3) | 2.732 (2) | 155 (3) |
O2—H4···O1ii | 0.91 (5) | 2.14 (5) | 2.948 (3) | 147 (4) |
O2—H3···O11iii | 0.85 (4) | 2.02 (4) | 2.870 (3) | 176 (4) |
O2—H4···O52iv | 0.91 (5) | 2.44 (5) | 3.039 (3) | 124 (4) |
N1—H13···O1 | 0.84 (5) | 3.15 (4) | 3.554 (3) | 113 (3) |
N1—H11···O2i | 0.98 (4) | 1.95 (4) | 2.919 (3) | 169 (4) |
N1—H12···O11v | 1.00 (4) | 1.87 (4) | 2.850 (3) | 165 (4) |
N1—H13···O1i | 0.84 (5) | 2.13 (5) | 2.941 (3) | 163 (4) |
N1—H14···O2 | 0.93 (5) | 2.15 (5) | 2.999 (4) | 152 (4) |
N2—H22···O2 | 0.93 (3) | 2.99 (2) | 3.448 (3) | 111.9 (16) |
N2—H23···O12 | 0.91 (3) | 1.93 (3) | 2.816 (2) | 164 (2) |
N2—H21···O51vi | 0.95 (3) | 1.84 (3) | 2.788 (3) | 178 (2) |
N2—H22···O52iv | 0.93 (3) | 1.98 (3) | 2.905 (3) | 175 (2) |
N2—H24···O11vii | 0.98 (3) | 2.62 (3) | 3.293 (3) | 126 (2) |
N2—H24···O12vii | 0.98 (3) | 1.81 (3) | 2.787 (2) | 177 (3) |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x, −y, −z+1; (iv) x−1, y, z; (v) −x+1, −y, −z+2; (vi) x, y, z+1; (vii) −x, −y, −z+2. |
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