A hydrogen-bonded chain of rings in (E)-3-(4-nitro­phenyl­amino­carbon­yl)prop-2-enoic acid

Wardell, J.L.; Skakle, J.M.S.; Low, J.N.; Glidewell, C.

doi:10.1107/S160053680503374X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 11| November 2005| Pages o3849-o3851

https://doi.org/10.1107/S160053680503374X

A hydrogen-bonded chain of rings in (E)-3-(4-nitrophenylaminocarbonyl)prop-2-enoic acid

James L. Wardell,^a Janet M. S. Skakle,^b John N. Low ^b and Christopher Glidewell ^c ^*

^aInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 12 October 2005; accepted 19 October 2005; online 27 October 2005)

In the title compound, C₁₀H₈N₂O₅, the molecules are linked into chains of rings by the concerted action of one N—H⋯O and one C—H⋯O hydrogen bond.

Comment

We have recently reported the molecular and supramolecular structures of two 2-(X-nitrophenylaminocarbonyl)benzoic acids (X = 2 and 4), formed from phthalic anhydride and the appropriate nitroaniline (Glidewell et al., 2004 ). We now report the related compound (E)-3-(4-nitrophenylaminocarbonyl)propen-2-oic acid, (I) (Fig. 1), formed from maleic anhydride and 4-nitroaniline. Although the molecule of (I) is simple, it contains a number of potential sites for involvement in intermolecular interactions; in particular, hard and soft hydrogen bonds and aromatic π-π stacking interactions are possible.

There are two intramolecular hydrogen bonds in compound (I). A rather short and almost linear O—H⋯O hydrogen bond (Fig. 1) controls the conformation of the maleate fragment, forming an S(7) ring, while a weaker C—H⋯O hydrogen bond forming an S(6) ring appears to control the mutual orientation of the maleate and nitroaryl fragments. Accordingly, the molecular skeleton is almost planar, as shown by the relevant torsion angles (Table 1). The bond distances within the acyclic portion of the molecule (Table 1) clearly show the location of single and double bonds; the C—O distances in the carboxylic acid group are consistent with the location of the carboxyl H atom deduced from difference maps.

The molecules of (I) are linked into chains of rings by an N—H⋯O hydrogen bond, augmented by a rather long C—H⋯O hydrogen bond. Amide atom N1 and aryl atom C16 in the molecule at (x, y, z) both act as hydrogen-bond donors to carboxyl atom O44 in the molecule at (1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z), so forming a C(7)C(9)[R₁²(6)] (Bernstein et al., 1995 ) chain of rings running parallel to the [010] direction and generated by the 2₁ screw axis along ( $[{1\over 2}]$ , y, $[{3\over 4}]$ ) (Fig. 2). Two chains of this type pass through each unit cell but there are no significant direction-specific interactions between adjacent chains; in particular, C—H⋯π(arene) hydrogen bonds and aromatic π–π stacking interactions are absent.

Figure 1
The molecule of compound (I)

, showing displacement ellipsoids drawn at the 30% probability level. The dashed line indicates a hydrogen bond.

Figure 2
Part of the crystal structure of (I)

, showing the formation of a chain of rings along [010]. Atoms marked with an asterisk (*) or an ampersand (&) are at the symmetry positions (1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z) and (1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z), respectively. Dashed lines indicate hydrogen bonds. H atoms have been omitted.

Experimental

A solution containing equimolar quantities of maleic anhydride and 4-nitroaniline (2 mmol of each) in diethyl ether (20 ml) was heated under reflux for 1 h and then left overnight at room temperature. The solvent was removed under reduced pressure and the resulting solid product was recrystallized from ethanol (m.p. 472–474 K). IR (cm⁻¹): 3200–2000 (br), 1707, 1635, 1596, 1566, 1497, 1457, 1407, 1335, 1307, 1271, 1230, 1110, 971, 898, 863, 797, 750, 687, 610, 597, 501, 432.

Crystal data

C₁₀H₈N₂O₅
M_r = 236.18
Monoclinic, P 2₁ /c
a = 9.6052 (7) Å
b = 12.8416 (10) Å
c = 9.0921 (7) Å
β = 114.388 (2)°
V = 1021.41 (13) Å³
Z = 4
D_x = 1.536 Mg m⁻³
Mo Kα radiation
Cell parameters from 2702 reflections
θ = 2.8–29.0°
μ = 0.13 mm⁻¹
T = 291 (2) K
Block, yellow
0.27 × 0.14 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Bruker, 2000 )T_min = 0.956, T_max = 0.988
8437 measured reflections
2702 independent reflections
1379 reflections with I > 2σ(I)
R_int = 0.042
θ_max = 29.0°
h = −13 → 13
k = −17 → 17
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.116
S = 0.87
2702 reflections
155 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0597P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1—O1	1.2413 (19)
C1—C2	1.478 (2)
C2—C3	1.328 (2)
C3—C4	1.482 (3)
C4—O43	1.307 (2)
C4—O44	1.206 (2)

C13—C14—N14—O41	−6.8 (3)
C12—C11—N1—C1	−0.5 (3)
C11—N1—C1—C2	177.37 (17)
N1—C1—C2—C3	175.98 (19)
C2—C3—C4—O43	3.3 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O43—H43⋯O1	0.82	1.72	2.537 (2)	174
C12—H12⋯O1	0.93	2.31	2.899 (2)	121
N1—H1⋯O44ⁱ	0.86	1.96	2.814 (2)	172
C16—H16⋯O44ⁱ	0.93	2.50	3.260 (2)	139
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

All H atoms were located in difference maps and then treated as riding atoms, with distances C—H = 0.93 Å, N—H 0.86 Å and O—H = 0.82 Å, and with U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(O).

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680503374X/lh6526sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680503374X/lh6526Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

(E)-3-(4-nitrophenylaminocarbonyl)propen-2-oic acid top

Crystal data top

C₁₀H₈N₂O₅	F(000) = 488
M_r = 236.18	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2702 reflections
a = 9.6052 (7) Å	θ = 2.8–29.0°
b = 12.8416 (10) Å	µ = 0.13 mm⁻¹
c = 9.0921 (7) Å	T = 291 K
β = 114.388 (2)°	Plate, yellow
V = 1021.41 (13) Å³	0.27 × 0.14 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2702 independent reflections
Radiation source: fine-focus sealed X-ray tube	1379 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ–ω scans	θ_max = 29.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
T_min = 0.956, T_max = 0.988	k = −17→17
8437 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0597P)²] where P = (F_o² + 2F_c²)/3
2702 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.72801 (13)	0.03077 (9)	0.65778 (16)	0.0570 (4)
O41	1.28952 (17)	0.24682 (13)	0.4548 (2)	0.0831 (5)
O42	1.22748 (17)	0.40730 (12)	0.45950 (19)	0.0764 (5)
O43	0.54851 (15)	−0.10562 (9)	0.68397 (18)	0.0606 (4)
O44	0.36370 (16)	−0.10330 (10)	0.7637 (2)	0.0779 (5)
N1	0.74726 (15)	0.20691 (11)	0.67282 (18)	0.0472 (4)
N14	1.21330 (18)	0.31419 (15)	0.4797 (2)	0.0592 (4)
C1	0.68626 (19)	0.11613 (13)	0.6895 (2)	0.0452 (4)
C2	0.5665 (2)	0.12856 (14)	0.7505 (2)	0.0511 (5)
C3	0.47741 (19)	0.05686 (14)	0.7728 (2)	0.0518 (5)
C4	0.4612 (2)	−0.05654 (14)	0.7397 (2)	0.0513 (5)
C11	0.86599 (18)	0.22698 (13)	0.6247 (2)	0.0432 (4)
C12	0.9471 (2)	0.15067 (14)	0.5844 (2)	0.0525 (5)
C13	1.0627 (2)	0.17921 (15)	0.5391 (2)	0.0535 (5)
C14	1.09543 (19)	0.28272 (14)	0.5340 (2)	0.0473 (4)
C15	1.01897 (19)	0.35913 (14)	0.5764 (2)	0.0506 (5)
C16	0.9034 (2)	0.33121 (13)	0.6206 (2)	0.0490 (5)
H1	0.7074	0.2613	0.6951	0.057*
H2	0.5513	0.1963	0.7771	0.061*
H3	0.4131	0.0827	0.8175	0.062*
H12	0.9237	0.0807	0.5879	0.063*
H13	1.1176	0.1287	0.5124	0.064*
H15	1.0449	0.4288	0.5752	0.061*
H16	0.8499	0.3824	0.6480	0.059*
H43	0.6074	−0.0641	0.6711	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0632 (8)	0.0394 (7)	0.0860 (10)	0.0039 (6)	0.0485 (8)	0.0025 (6)
O41	0.0746 (10)	0.0901 (12)	0.1107 (13)	0.0030 (8)	0.0647 (11)	−0.0045 (9)
O42	0.0798 (10)	0.0701 (11)	0.0976 (12)	−0.0170 (8)	0.0549 (10)	0.0073 (8)
O43	0.0678 (9)	0.0419 (7)	0.0883 (10)	−0.0045 (6)	0.0485 (8)	−0.0033 (7)
O44	0.0809 (10)	0.0540 (9)	0.1270 (14)	−0.0141 (7)	0.0711 (10)	0.0005 (8)
N1	0.0492 (9)	0.0366 (8)	0.0661 (10)	0.0007 (6)	0.0343 (8)	0.0008 (7)
N14	0.0509 (10)	0.0737 (12)	0.0605 (11)	−0.0059 (8)	0.0306 (9)	−0.0009 (9)
C1	0.0464 (10)	0.0390 (10)	0.0559 (11)	0.0013 (8)	0.0268 (9)	0.0046 (8)
C2	0.0551 (11)	0.0375 (9)	0.0710 (13)	0.0022 (8)	0.0364 (11)	0.0010 (9)
C3	0.0532 (11)	0.0458 (11)	0.0689 (13)	0.0022 (8)	0.0379 (11)	0.0011 (9)
C4	0.0511 (11)	0.0440 (10)	0.0664 (13)	0.0000 (8)	0.0318 (10)	0.0040 (9)
C11	0.0434 (10)	0.0420 (10)	0.0487 (11)	−0.0006 (7)	0.0238 (9)	0.0008 (8)
C12	0.0559 (11)	0.0395 (10)	0.0705 (13)	−0.0012 (8)	0.0344 (11)	−0.0020 (9)
C13	0.0524 (11)	0.0507 (11)	0.0662 (13)	0.0033 (8)	0.0332 (11)	−0.0052 (9)
C14	0.0431 (10)	0.0546 (11)	0.0488 (11)	−0.0034 (8)	0.0235 (9)	0.0014 (9)
C15	0.0543 (11)	0.0425 (10)	0.0611 (12)	−0.0047 (8)	0.0300 (11)	0.0032 (9)
C16	0.0551 (11)	0.0385 (10)	0.0616 (12)	0.0023 (8)	0.0324 (10)	0.0012 (8)

Geometric parameters (Å, º) top

C11—C16	1.391 (2)	N14—O42	1.226 (2)
C11—C12	1.392 (2)	N1—C1	1.341 (2)
C11—N1	1.4037 (19)	N1—H1	0.86
C12—C13	1.383 (2)	C1—O1	1.2413 (19)
C12—H12	0.93	C1—C2	1.478 (2)
C13—C14	1.371 (3)	C2—C3	1.328 (2)
C13—H13	0.93	C2—H2	0.93
C14—C15	1.373 (2)	C3—C4	1.482 (3)
C14—N14	1.467 (2)	C3—H3	0.93
C15—C16	1.375 (2)	C4—O43	1.307 (2)
C15—H15	0.93	C4—O44	1.206 (2)
C16—H16	0.93	O43—H43	0.82
N14—O41	1.214 (2)

C16—C11—C12	119.45 (15)	O41—N14—C14	118.40 (17)
C16—C11—N1	115.95 (14)	O42—N14—C14	117.92 (16)
C12—C11—N1	124.60 (15)	C1—N1—C11	130.08 (14)
C13—C12—C11	119.81 (16)	C1—N1—H1	115.0
C13—C12—H12	120.1	C11—N1—H1	115.0
C11—C12—H12	120.1	O1—C1—N1	122.92 (15)
C14—C13—C12	119.36 (16)	O1—C1—C2	123.96 (15)
C14—C13—H13	120.3	N1—C1—C2	113.12 (15)
C12—C13—H13	120.3	C3—C2—C1	129.25 (17)
C13—C14—C15	121.78 (15)	C3—C2—H2	115.4
C13—C14—N14	119.88 (16)	C1—C2—H2	115.4
C15—C14—N14	118.33 (16)	C2—C3—C4	132.11 (17)
C14—C15—C16	119.06 (16)	C2—C3—H3	113.9
C14—C15—H15	120.5	C4—C3—H3	113.9
C16—C15—H15	120.5	O44—C4—O43	120.03 (17)
C15—C16—C11	120.52 (16)	O44—C4—C3	118.49 (17)
C15—C16—H16	119.7	O43—C4—C3	121.47 (15)
C11—C16—H16	119.7	C4—O43—H43	109.5
O41—N14—O42	123.67 (16)

C16—C11—C12—C13	−0.7 (3)	C13—C14—N14—O42	171.96 (18)
N1—C11—C12—C13	−179.74 (17)	C15—C14—N14—O42	−7.1 (3)
C11—C12—C13—C14	−0.2 (3)	C16—C11—N1—C1	−179.60 (17)
C12—C13—C14—C15	1.6 (3)	C12—C11—N1—C1	−0.5 (3)
C12—C13—C14—N14	−177.45 (17)	C11—N1—C1—O1	−2.0 (3)
C13—C14—C15—C16	−1.9 (3)	C11—N1—C1—C2	177.37 (17)
N14—C14—C15—C16	177.11 (16)	O1—C1—C2—C3	−4.6 (3)
C14—C15—C16—C11	0.9 (3)	N1—C1—C2—C3	175.98 (19)
C12—C11—C16—C15	0.4 (3)	C1—C2—C3—C4	−2.9 (4)
N1—C11—C16—C15	179.46 (15)	C2—C3—C4—O44	−175.9 (2)
C13—C14—N14—O41	−6.8 (3)	C2—C3—C4—O43	3.3 (3)
C15—C14—N14—O41	174.12 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O43—H43···O1	0.82	1.72	2.537 (2)	174
C12—H12···O1	0.93	2.31	2.899 (2)	121
N1—H1···O44ⁱ	0.86	1.96	2.814 (2)	172
C16—H16···O44ⁱ	0.93	2.50	3.260 (2)	139

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors thank the University of Aberdeen for funding the purchase of the Bruker SMART 1000 diffractometer. JLW thanks CNPq and FAPERJ for financial support.

References

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