Benzene-1,2,4,5-tetra­carboxyl­ic acid-trans-cinnam­amide (1/2)

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.

Computing details

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)

Crystal data

C10H6O8·2C9H9NO	Dx = 1.330 Mg m^−3
Mr = 548.51	Mo Kα radiation, λ = 0.71073 Å
Monoclinic, C2/c	Cell parameters from 24 reflections
a = 7.163 (2) Å	θ = 12.2–14.4°
b = 39.861 (9) Å	µ = 0.10 mm^−1
c = 10.053 (3) Å	T = 298 K
β = 107.40 (2)°	Plate, colourless
V = 2739.1 (14) Å^3	0.4 × 0.4 × 0.1 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
ω scans	h = −9→0
3396 measured reflections	k = 0→52
3157 independent reflections	l = −13→13
1298 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.028	intensity decay: none

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0643P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.060	(Δ/σ)max = 0.001
wR(F^2) = 0.158	Δρmax = 0.21 e Å^−3
S = 0.95	Δρmin = −0.26 e Å^−3
3157 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
234 parameters	Extinction coefficient: 0.0018 (4)
All H-atom parameters refined

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.5735 (4)	0.33059 (5)	0.5127 (2)	0.0511 (7)
O2	0.3497 (4)	0.31515 (5)	0.3144 (2)	0.0487 (7)
O3	0.6009 (6)	0.46199 (6)	0.5189 (3)	0.092 (1)
O4	0.3745 (5)	0.48197 (6)	0.3385 (3)	0.097 (1)
O5	0.3719 (3)	0.25414 (5)	0.3828 (2)	0.0460 (6)
N6	0.5890 (5)	0.26039 (7)	0.5949 (3)	0.0505 (8)
C7	0.4789 (5)	0.33585 (7)	0.3927 (3)	0.0370 (7)
C8	0.4940 (5)	0.36777 (6)	0.3181 (3)	0.0367 (8)
C9	0.4951 (5)	0.39797 (7)	0.3875 (3)	0.0440 (8)
C10	0.4990 (5)	0.42825 (7)	0.3193 (3)	0.0451 (9)
C11	0.4942 (6)	0.45973 (8)	0.3981 (3)	0.054 (1)
C12	0.4787 (5)	0.24130 (7)	0.4933 (3)	0.0413 (8)
C13	0.4868 (5)	0.20497 (8)	0.5149 (3)	0.0459 (9)
C14	0.3884 (6)	0.18350 (8)	0.4205 (3)	0.0477 (9)
C15	0.3859 (5)	0.14689 (8)	0.4306 (3)	0.0483 (9)
C16	0.2855 (7)	0.12791 (9)	0.3169 (4)	0.072 (1)
C17	0.2863 (9)	0.0934 (1)	0.3212 (5)	0.089 (2)
C18	0.3872 (7)	0.0768 (1)	0.4409 (5)	0.074 (1)
C19	0.4841 (7)	0.0953 (1)	0.5556 (5)	0.076 (1)
C20	0.4855 (6)	0.12981 (9)	0.5519 (4)	0.062 (1)
H2	0.358 (6)	0.2927 (5)	0.354 (4)	0.0935 (2)*
H3	0.550 (13)	0.480 (2)	0.565 (9)	0.1203 (5)*	0.50
H4	0.354 (10)	0.5023 (10)	0.387 (6)	0.0599 (3)*	0.50
H6A	0.596 (6)	0.2825 (3)	0.590 (4)	0.0819 (2)*
H6B	0.664 (4)	0.2515 (8)	0.671 (2)	0.0631 (1)*
H9	0.479 (5)	0.3980 (7)	0.482 (3)	0.0493 (1)*
H13	0.572 (6)	0.1964 (9)	0.605 (4)	0.0802 (2)*
H14	0.305 (5)	0.1911 (8)	0.331 (3)	0.0576 (1)*
H16	0.215 (7)	0.139 (1)	0.237 (5)	0.1044 (2)*
H17	0.225 (7)	0.081 (1)	0.247 (5)	0.1058 (2)*
H18	0.394 (5)	0.0502 (10)	0.440 (3)	0.0735 (1)*
H19	0.551 (7)	0.084 (1)	0.636 (5)	0.1208 (2)*
H20	0.570 (7)	0.142 (1)	0.632 (5)	0.1126 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.079 (2)	0.034 (1)	0.028 (1)	−0.009 (1)	−0.003 (1)	0.0025 (9)
O2	0.066 (2)	0.030 (1)	0.037 (1)	−0.008 (1)	−0.003 (1)	0.0057 (9)
O3	0.139 (3)	0.050 (2)	0.060 (2)	0.028 (2)	−0.014 (2)	−0.021 (1)
O4	0.157 (3)	0.046 (2)	0.062 (2)	0.043 (2)	−0.008 (2)	−0.016 (1)
O5	0.059 (1)	0.033 (1)	0.034 (1)	−0.005 (1)	−0.005 (1)	0.0071 (9)
N6	0.060 (2)	0.042 (2)	0.036 (2)	−0.007 (2)	−0.008 (1)	0.005 (1)
C7	0.053 (2)	0.024 (1)	0.033 (2)	0.000 (1)	0.011 (2)	0.001 (1)
C8	0.051 (2)	0.025 (1)	0.031 (1)	0.003 (1)	0.008 (1)	−0.001 (1)
C9	0.067 (2)	0.031 (2)	0.032 (2)	0.002 (2)	0.013 (2)	−0.003 (1)
C10	0.068 (3)	0.026 (2)	0.040 (2)	0.003 (2)	0.015 (2)	−0.004 (1)
C11	0.089 (3)	0.028 (2)	0.043 (2)	0.005 (2)	0.016 (2)	0.000 (1)
C12	0.042 (2)	0.043 (2)	0.037 (2)	−0.001 (2)	0.008 (1)	0.006 (1)
C13	0.050 (2)	0.039 (2)	0.040 (2)	−0.004 (2)	0.001 (2)	0.009 (1)
C14	0.056 (2)	0.040 (2)	0.041 (2)	0.003 (2)	0.006 (2)	0.014 (1)
C15	0.054 (2)	0.038 (2)	0.050 (2)	0.004 (2)	0.010 (2)	0.006 (1)
C16	0.099 (4)	0.046 (2)	0.053 (2)	−0.002 (2)	−0.004 (2)	0.001 (2)
C17	0.128 (5)	0.050 (3)	0.073 (3)	−0.011 (3)	0.008 (3)	−0.012 (2)
C18	0.087 (3)	0.038 (2)	0.096 (3)	0.002 (2)	0.026 (3)	0.006 (2)
C19	0.079 (3)	0.050 (3)	0.084 (3)	0.003 (2)	0.003 (3)	0.025 (2)
C20	0.062 (3)	0.044 (2)	0.064 (2)	0.000 (2)	−0.008 (2)	0.010 (2)

Geometric parameters (Å, º)

O1—C7	1.212 (3)	C10—C11	1.490 (4)
O2—C7	1.312 (3)	C12—C13	1.463 (4)
O2—H2	0.98 (2)	C13—C14	1.315 (4)
O3—C11	1.231 (4)	C13—H13	0.99 (3)
O3—H3	0.98 (8)	C14—C15	1.463 (4)
O4—C11	1.254 (4)	C14—H14	0.97 (3)
O4—H4	0.98 (5)	C15—C16	1.380 (5)
O5—C12	1.254 (3)	C15—C20	1.393 (5)
N6—C12	1.328 (4)	C16—C17	1.377 (5)
N6—H6A	0.88 (1)	C16—H16	0.93 (4)
N6—H6B	0.87 (2)	C17—C18	1.373 (6)
C7—C8	1.498 (4)	C17—H17	0.88 (4)
C8—C8^i	1.396 (6)	C18—C19	1.370 (6)
C8—C9	1.391 (4)	C18—H18	1.06 (4)
C9—C10	1.393 (4)	C19—C20	1.375 (5)
C9—H9	0.99 (3)	C19—H19	0.93 (4)
C10—C10^i	1.397 (6)	C20—H20	0.99 (4)
C7—O2—H2	112 (1)	C12—C13—C14	123.3 (3)
C11—O3—H3	108 (4)	C12—C13—H13	117 (2)
C11—O4—H4	122 (3)	C14—C13—H13	119 (2)
C12—N6—H6A	123 (2)	C13—C14—C15	127.9 (3)
C12—N6—H6B	120 (1)	C13—C14—H14	121 (1)
H6A—N6—H6B	115 (2)	C15—C14—H14	111 (1)
O1—C7—O2	124.9 (3)	C14—C15—C16	120.2 (3)
O1—C7—C8	122.9 (3)	C14—C15—C20	122.3 (3)
O2—C7—C8	112.2 (2)	C16—C15—C20	117.4 (3)
C7—C8—C8^i	121.7 (2)	C15—C16—C17	121.8 (4)
C7—C8—C9	118.3 (3)	C15—C16—H16	117 (2)
C8^i—C8—C9	120.0 (2)	C17—C16—H16	120 (2)
C8—C9—C10	120.1 (3)	C16—C17—C18	120.2 (4)
C8—C9—H9	119 (1)	C16—C17—H17	121 (2)
C10—C9—H9	119 (1)	C18—C17—H17	118 (2)
C9—C10—C10^i	119.9 (2)	C17—C18—C19	118.8 (4)
C9—C10—C11	117.5 (3)	C17—C18—H18	119 (1)
C10^i—C10—C11	122.6 (2)	C19—C18—H18	122 (1)
O3—C11—O4	123.6 (3)	C18—C19—C20	121.4 (4)
O3—C11—C10	118.7 (3)	C18—C19—H19	118 (2)
O4—C11—C10	117.6 (3)	C20—C19—H19	120 (2)
O5—C12—N6	120.8 (3)	C15—C20—C19	120.4 (3)
O5—C12—C13	121.4 (3)	C15—C20—H20	119 (2)
N6—C12—C13	117.7 (3)	C19—C20—H20	119 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5	0.98 (2)	1.56 (2)	2.520 (3)	166 (4)
O3—H3···O4^ii	0.98 (8)	1.79 (7)	2.631 (4)	141 (8)
O4—H4···O3^ii	0.98 (5)	1.69 (4)	2.631 (4)	161 (6)
N6—H6A···O1	0.88 (1)	2.06 (2)	2.910 (3)	162 (3)
N6—H6B···O5^iii	0.87 (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.