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In the title adduct, C10H6O8·2C9H9NO, benzene-1,2,4,5-tetra­car­box­ylic acid has a crystallographic twofold axis parallel to b and forms a flat zigzag chain along c linked by O- H...O cyclic hydrogen bonds with cinnam­amide mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013391/qa0404sup1.cif
Contains datablocks cocryp, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013391/qa0404Isup2.hkl
Contains datablock I

CCDC reference: 153940

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C10H6O8·2C9H9NODx = 1.330 Mg m3
Mr = 548.51Mo Kα radiation, λ = 0.71073 Å
Monoclinic, C2/cCell parameters from 24 reflections
a = 7.163 (2) Åθ = 12.2–14.4°
b = 39.861 (9) ŵ = 0.10 mm1
c = 10.053 (3) ÅT = 298 K
β = 107.40 (2)°Plate, colourless
V = 2739.1 (14) Å30.4 × 0.4 × 0.1 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°, θmin = 2.5°
ω scansh = 90
3396 measured reflectionsk = 052
3157 independent reflectionsl = 1313
1298 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.028 intensity decay: none
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0643P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.060(Δ/σ)max = 0.001
wR(F2) = 0.158Δρmax = 0.21 e Å3
S = 0.95Δρmin = 0.26 e Å3
3157 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
234 parametersExtinction coefficient: 0.0018 (4)
All H-atom parameters refined
Special details top

Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.5735 (4)0.33059 (5)0.5127 (2)0.0511 (7)
O20.3497 (4)0.31515 (5)0.3144 (2)0.0487 (7)
O30.6009 (6)0.46199 (6)0.5189 (3)0.092 (1)
O40.3745 (5)0.48197 (6)0.3385 (3)0.097 (1)
O50.3719 (3)0.25414 (5)0.3828 (2)0.0460 (6)
N60.5890 (5)0.26039 (7)0.5949 (3)0.0505 (8)
C70.4789 (5)0.33585 (7)0.3927 (3)0.0370 (7)
C80.4940 (5)0.36777 (6)0.3181 (3)0.0367 (8)
C90.4951 (5)0.39797 (7)0.3875 (3)0.0440 (8)
C100.4990 (5)0.42825 (7)0.3193 (3)0.0451 (9)
C110.4942 (6)0.45973 (8)0.3981 (3)0.054 (1)
C120.4787 (5)0.24130 (7)0.4933 (3)0.0413 (8)
C130.4868 (5)0.20497 (8)0.5149 (3)0.0459 (9)
C140.3884 (6)0.18350 (8)0.4205 (3)0.0477 (9)
C150.3859 (5)0.14689 (8)0.4306 (3)0.0483 (9)
C160.2855 (7)0.12791 (9)0.3169 (4)0.072 (1)
C170.2863 (9)0.0934 (1)0.3212 (5)0.089 (2)
C180.3872 (7)0.0768 (1)0.4409 (5)0.074 (1)
C190.4841 (7)0.0953 (1)0.5556 (5)0.076 (1)
C200.4855 (6)0.12981 (9)0.5519 (4)0.062 (1)
H20.358 (6)0.2927 (5)0.354 (4)0.0935 (2)*
H30.550 (13)0.480 (2)0.565 (9)0.1203 (5)*0.50
H40.354 (10)0.5023 (10)0.387 (6)0.0599 (3)*0.50
H6A0.596 (6)0.2825 (3)0.590 (4)0.0819 (2)*
H6B0.664 (4)0.2515 (8)0.671 (2)0.0631 (1)*
H90.479 (5)0.3980 (7)0.482 (3)0.0493 (1)*
H130.572 (6)0.1964 (9)0.605 (4)0.0802 (2)*
H140.305 (5)0.1911 (8)0.331 (3)0.0576 (1)*
H160.215 (7)0.139 (1)0.237 (5)0.1044 (2)*
H170.225 (7)0.081 (1)0.247 (5)0.1058 (2)*
H180.394 (5)0.0502 (10)0.440 (3)0.0735 (1)*
H190.551 (7)0.084 (1)0.636 (5)0.1208 (2)*
H200.570 (7)0.142 (1)0.632 (5)0.1126 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.079 (2)0.034 (1)0.028 (1)0.009 (1)0.003 (1)0.0025 (9)
O20.066 (2)0.030 (1)0.037 (1)0.008 (1)0.003 (1)0.0057 (9)
O30.139 (3)0.050 (2)0.060 (2)0.028 (2)0.014 (2)0.021 (1)
O40.157 (3)0.046 (2)0.062 (2)0.043 (2)0.008 (2)0.016 (1)
O50.059 (1)0.033 (1)0.034 (1)0.005 (1)0.005 (1)0.0071 (9)
N60.060 (2)0.042 (2)0.036 (2)0.007 (2)0.008 (1)0.005 (1)
C70.053 (2)0.024 (1)0.033 (2)0.000 (1)0.011 (2)0.001 (1)
C80.051 (2)0.025 (1)0.031 (1)0.003 (1)0.008 (1)0.001 (1)
C90.067 (2)0.031 (2)0.032 (2)0.002 (2)0.013 (2)0.003 (1)
C100.068 (3)0.026 (2)0.040 (2)0.003 (2)0.015 (2)0.004 (1)
C110.089 (3)0.028 (2)0.043 (2)0.005 (2)0.016 (2)0.000 (1)
C120.042 (2)0.043 (2)0.037 (2)0.001 (2)0.008 (1)0.006 (1)
C130.050 (2)0.039 (2)0.040 (2)0.004 (2)0.001 (2)0.009 (1)
C140.056 (2)0.040 (2)0.041 (2)0.003 (2)0.006 (2)0.014 (1)
C150.054 (2)0.038 (2)0.050 (2)0.004 (2)0.010 (2)0.006 (1)
C160.099 (4)0.046 (2)0.053 (2)0.002 (2)0.004 (2)0.001 (2)
C170.128 (5)0.050 (3)0.073 (3)0.011 (3)0.008 (3)0.012 (2)
C180.087 (3)0.038 (2)0.096 (3)0.002 (2)0.026 (3)0.006 (2)
C190.079 (3)0.050 (3)0.084 (3)0.003 (2)0.003 (3)0.025 (2)
C200.062 (3)0.044 (2)0.064 (2)0.000 (2)0.008 (2)0.010 (2)
Geometric parameters (Å, º) top
O1—C71.212 (3)C10—C111.490 (4)
O2—C71.312 (3)C12—C131.463 (4)
O2—H20.98 (2)C13—C141.315 (4)
O3—C111.231 (4)C13—H130.99 (3)
O3—H30.98 (8)C14—C151.463 (4)
O4—C111.254 (4)C14—H140.97 (3)
O4—H40.98 (5)C15—C161.380 (5)
O5—C121.254 (3)C15—C201.393 (5)
N6—C121.328 (4)C16—C171.377 (5)
N6—H6A0.88 (1)C16—H160.93 (4)
N6—H6B0.87 (2)C17—C181.373 (6)
C7—C81.498 (4)C17—H170.88 (4)
C8—C8i1.396 (6)C18—C191.370 (6)
C8—C91.391 (4)C18—H181.06 (4)
C9—C101.393 (4)C19—C201.375 (5)
C9—H90.99 (3)C19—H190.93 (4)
C10—C10i1.397 (6)C20—H200.99 (4)
C7—O2—H2112 (1)C12—C13—C14123.3 (3)
C11—O3—H3108 (4)C12—C13—H13117 (2)
C11—O4—H4122 (3)C14—C13—H13119 (2)
C12—N6—H6A123 (2)C13—C14—C15127.9 (3)
C12—N6—H6B120 (1)C13—C14—H14121 (1)
H6A—N6—H6B115 (2)C15—C14—H14111 (1)
O1—C7—O2124.9 (3)C14—C15—C16120.2 (3)
O1—C7—C8122.9 (3)C14—C15—C20122.3 (3)
O2—C7—C8112.2 (2)C16—C15—C20117.4 (3)
C7—C8—C8i121.7 (2)C15—C16—C17121.8 (4)
C7—C8—C9118.3 (3)C15—C16—H16117 (2)
C8i—C8—C9120.0 (2)C17—C16—H16120 (2)
C8—C9—C10120.1 (3)C16—C17—C18120.2 (4)
C8—C9—H9119 (1)C16—C17—H17121 (2)
C10—C9—H9119 (1)C18—C17—H17118 (2)
C9—C10—C10i119.9 (2)C17—C18—C19118.8 (4)
C9—C10—C11117.5 (3)C17—C18—H18119 (1)
C10i—C10—C11122.6 (2)C19—C18—H18122 (1)
O3—C11—O4123.6 (3)C18—C19—C20121.4 (4)
O3—C11—C10118.7 (3)C18—C19—H19118 (2)
O4—C11—C10117.6 (3)C20—C19—H19120 (2)
O5—C12—N6120.8 (3)C15—C20—C19120.4 (3)
O5—C12—C13121.4 (3)C15—C20—H20119 (2)
N6—C12—C13117.7 (3)C19—C20—H20119 (2)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O50.98 (2)1.56 (2)2.520 (3)166 (4)
O3—H3···O4ii0.98 (8)1.79 (7)2.631 (4)141 (8)
O4—H4···O3ii0.98 (5)1.69 (4)2.631 (4)161 (6)
N6—H6A···O10.88 (1)2.06 (2)2.910 (3)162 (3)
N6—H6B···O5iii0.87 (2)2.22 (2)3.052 (3)162 (3)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1/2, y+1/2, z+1/2.
 

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