N-(p-Tolyl)­maleamic acid

The title mol­ecule, C₁₁H₁₁NO₃, is nearly planar, with the mean planes through the p-tolyl and maleamic acid groups inclined at an angle of 5.45 (3)°. The glide-related mol­ecules are linked by N—H...O and C—H...O intermolecular hydrogen bonds, forming infinite one-dimensional chains, which are assembled to form layers parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.177
• Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair,1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-(p-tolyl)-maleamic acid

Crystal data

C11H11NO3	F(000) = 432
Mr = 205.21	Dx = 1.326 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.769 (2) Å	θ = 28.2–36.3°
b = 12.109 (1) Å	µ = 0.81 mm^−1
c = 12.606 (1) Å	T = 293 K
β = 95.73 (1)°	Needle, colourless
V = 1028.1 (3) Å^3	0.38 × 0.31 × 0.25 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	1200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 75.5°, θmin = 5.1°
ω–2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.733, Tmax = 0.817	l = −15→15
2123 measured reflections	3 standard reflections every 1 hr min
2047 independent reflections	intensity decay: nil

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.0899P)^2 + 0.2017P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
2047 reflections	Δρmax = 0.22 e Å^−3
167 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0101 (16)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2420 (5)	0.1723 (2)	0.4204 (2)	0.0654 (8)
C2	0.2701 (5)	0.2170 (2)	0.5217 (2)	0.0691 (9)
C3	0.2741 (5)	0.3296 (2)	0.5392 (2)	0.0657 (8)
C4	0.2493 (4)	0.4013 (2)	0.45319 (18)	0.0555 (7)
C5	0.2238 (5)	0.3576 (2)	0.35096 (19)	0.0604 (7)
C6	0.2200 (5)	0.2454 (2)	0.3356 (2)	0.0650 (8)
C7	0.2574 (4)	0.5802 (2)	0.55013 (17)	0.0554 (7)
C8	0.2537 (5)	0.6992 (2)	0.52794 (19)	0.0612 (8)
C9	0.2582 (5)	0.7831 (2)	0.5970 (2)	0.0632 (8)
C10	0.2671 (5)	0.7875 (2)	0.7149 (2)	0.0640 (8)
C11	0.2372 (6)	0.0498 (2)	0.4018 (3)	0.0925 (12)
N	0.2509 (4)	0.51755 (17)	0.46196 (16)	0.0575 (6)
O1	0.2794 (4)	0.69723 (15)	0.77065 (13)	0.0796 (7)
O2	0.2624 (4)	0.87728 (16)	0.75734 (15)	0.0857 (8)
O3	0.2652 (3)	0.54085 (14)	0.64121 (13)	0.0714 (6)
H2	0.291 (4)	0.168 (3)	0.584 (3)	0.073 (8)*
H3	0.296 (4)	0.358 (2)	0.612 (2)	0.069 (8)*
H5	0.198 (4)	0.407 (2)	0.293 (2)	0.059 (7)*
H6	0.206 (4)	0.220 (2)	0.264 (2)	0.059 (7)*
H8	0.244 (3)	0.7152 (19)	0.452 (2)	0.048 (7)*
H9	0.260 (4)	0.857 (3)	0.569 (2)	0.077 (9)*
H1N	0.259 (4)	0.552 (2)	0.397 (2)	0.069 (8)*
H1O	0.2828	0.6440	0.7307	0.119*
H11A	0.2195	0.0125	0.4674	0.139*
H11B	0.1291	0.0319	0.3495	0.139*
H11C	0.3600	0.0267	0.3767	0.139*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.099 (2)	0.0458 (13)	0.0535 (14)	−0.0008 (14)	0.0188 (14)	−0.0053 (11)
C2	0.114 (3)	0.0500 (14)	0.0452 (14)	0.0048 (16)	0.0166 (14)	0.0066 (12)
C3	0.115 (3)	0.0475 (14)	0.0366 (12)	0.0009 (15)	0.0151 (14)	−0.0010 (10)
C4	0.089 (2)	0.0430 (13)	0.0361 (11)	0.0002 (12)	0.0160 (11)	−0.0015 (9)
C5	0.100 (2)	0.0465 (13)	0.0365 (11)	0.0051 (14)	0.0139 (12)	0.0003 (10)
C6	0.104 (3)	0.0524 (14)	0.0411 (13)	−0.0018 (15)	0.0186 (13)	−0.0094 (11)
C7	0.0824 (19)	0.0513 (13)	0.0337 (10)	0.0010 (13)	0.0122 (11)	−0.0028 (9)
C8	0.104 (2)	0.0456 (14)	0.0364 (12)	0.0017 (13)	0.0161 (13)	−0.0004 (10)
C9	0.100 (2)	0.0441 (14)	0.0466 (14)	0.0029 (14)	0.0141 (13)	0.0005 (11)
C10	0.100 (2)	0.0477 (14)	0.0453 (13)	−0.0028 (15)	0.0119 (13)	−0.0077 (11)
C11	0.153 (4)	0.0499 (16)	0.076 (2)	0.0029 (19)	0.021 (2)	−0.0042 (15)
N	0.0976 (18)	0.0430 (11)	0.0332 (9)	0.0001 (11)	0.0134 (10)	0.0001 (8)
O1	0.152 (2)	0.0502 (10)	0.0370 (9)	0.0007 (12)	0.0135 (11)	−0.0030 (7)
O2	0.155 (2)	0.0525 (11)	0.0511 (11)	−0.0003 (12)	0.0155 (12)	−0.0167 (8)
O3	0.1308 (18)	0.0488 (10)	0.0365 (9)	0.0020 (11)	0.0176 (9)	−0.0005 (7)

Geometric parameters (Å, º)

C1—C2	1.382 (4)	C7—N	1.343 (3)
C1—C6	1.384 (4)	C7—C8	1.467 (4)
C1—C11	1.502 (4)	C8—C9	1.337 (3)
C2—C3	1.381 (4)	C8—H8	0.97 (3)
C2—H2	0.99 (3)	C9—C10	1.482 (3)
C3—C4	1.386 (3)	C9—H9	0.97 (3)
C3—H3	0.98 (3)	C10—O2	1.214 (3)
C4—C5	1.388 (3)	C10—O1	1.298 (3)
C4—N	1.412 (3)	C11—H11A	0.96
C5—C6	1.373 (4)	C11—H11B	0.96
C5—H5	0.94 (3)	C11—H11C	0.96
C6—H6	0.96 (3)	N—H1N	0.93 (3)
C7—O3	1.240 (3)	O1—H1O	0.82
C2—C1—C6	117.2 (2)	N—C7—C8	113.5 (2)
C2—C1—C11	122.0 (3)	C9—C8—C7	128.6 (2)
C6—C1—C11	120.8 (3)	C9—C8—H8	119.0 (14)
C1—C2—C3	122.2 (2)	C7—C8—H8	112.4 (14)
C1—C2—H2	119.9 (18)	C8—C9—C10	132.6 (2)
C3—C2—H2	117.9 (18)	C8—C9—H9	118.2 (19)
C4—C3—C2	119.6 (2)	C10—C9—H9	109.2 (19)
C4—C3—H3	121.0 (17)	O2—C10—O1	121.2 (2)
C2—C3—H3	119.4 (17)	O2—C10—C9	118.3 (2)
C3—C4—C5	118.8 (2)	O1—C10—C9	120.5 (2)
C3—C4—N	124.3 (2)	C1—C11—H11A	109.5
C5—C4—N	116.9 (2)	C1—C11—H11B	109.5
C6—C5—C4	120.5 (2)	H11A—C11—H11B	109.5
C6—C5—H5	121.3 (16)	C1—C11—H11C	109.5
C4—C5—H5	118.0 (16)	H11A—C11—H11C	109.5
C5—C6—C1	121.7 (2)	H11B—C11—H11C	109.5
C5—C6—H6	117.1 (16)	C7—N—C4	128.9 (2)
C1—C6—H6	121.2 (16)	C7—N—H1N	118.3 (17)
O3—C7—N	123.0 (2)	C4—N—H1N	112.6 (17)
O3—C7—C8	123.5 (2)	C10—O1—H1O	109.5
C6—C1—C2—C3	0.8 (5)	O3—C7—C8—C9	0.2 (6)
C11—C1—C2—C3	−179.8 (3)	N—C7—C8—C9	180.0 (3)
C1—C2—C3—C4	0.0 (5)	C7—C8—C9—C10	−0.3 (6)
C2—C3—C4—C5	−0.9 (5)	C8—C9—C10—O2	−177.4 (4)
C2—C3—C4—N	−180.0 (3)	C8—C9—C10—O1	2.5 (6)
C3—C4—C5—C6	1.0 (5)	O3—C7—N—C4	0.7 (5)
N—C4—C5—C6	−179.8 (3)	C8—C7—N—C4	−179.1 (3)
C4—C5—C6—C1	−0.3 (5)	C3—C4—N—C7	−6.6 (5)
C2—C1—C6—C5	−0.6 (5)	C5—C4—N—C7	174.3 (3)
C11—C1—C6—C5	180.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1N···O2^i	0.93 (3)	1.96 (3)	2.885 (3)	177 (2)
O1—H1O···O3	0.82	1.68	2.495 (2)	173
C3—H3···O3	0.98 (3)	2.26 (2)	2.866 (3)	119 (2)
C8—H8···O1^i	0.97 (3)	2.55 (2)	3.498 (3)	164 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.