N-(4-Meth-oxy-phen-yl)maleamic acid.

In the title compound, C(11)H(11)NO(4), the asymmetric unit contains two unique mol-ecules, both of which are almost planar, with r.m.s. deviations of 0.047 and 0.059 Å. The dihedral angles between the benzene ring and the plane of maleamic acid unit are 3.43 (5) and 5.79 (3)° in the two mol-ecules. The mol-ecular structures are stabilized by a short intra-molecular O-H⋯O hydrogen bond within each maleamic acid unit. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains extending along [10]. Weak intermolecular C-H⋯O hydrogen bonds also exist.

Related literature

For studies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda et al. (2009 ▶); Prasad et al. (2002 ▶). For the modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Jagannathan et al. (1994 ▶); Leiserowitz (1976 ▶).

Experimental

Crystal data

C11H11NO4

M = 221.21

Triclinic,

a = 7.34030 (17) Å

b = 11.8258 (4) Å

c = 12.1207 (4) Å

α = 89.103 (3)°

β = 88.358 (2)°

γ = 78.396 (2)°

V = 1030.15 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.54 × 0.25 × 0.22 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.962, T max = 0.980

15439 measured reflections

3711 independent reflections

2923 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.02

3711 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019999/bq2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019999/bq2215Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H11NO4	Z = 4
Mr = 221.21	F(000) = 464
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.34030 (17) Å	Cell parameters from 8581 reflections
b = 11.8258 (4) Å	θ = 1.8–29.5°
c = 12.1207 (4) Å	µ = 0.11 mm−1
α = 89.103 (3)°	T = 295 K
β = 88.358 (2)°	Prism, yellow–green
γ = 78.396 (2)°	0.54 × 0.25 × 0.22 mm
V = 1030.15 (5) Å3

Oxford Diffraction Gemini R CCD diffractometer	3711 independent reflections
graphite	2923 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.020
ω scans	θmax = 25.2°, θmin = 2.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.962, Tmax = 0.980	k = −14→14
15439 measured reflections	l = −14→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
3711 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.25076 (17)	0.51156 (11)	0.57066 (10)	0.0407 (3)
C2	0.23780 (18)	0.54345 (11)	0.68793 (11)	0.0431 (3)
H2	0.1732	0.6177	0.7035	0.052*
C3	0.30661 (18)	0.47979 (12)	0.77505 (11)	0.0466 (3)
H3	0.2826	0.5179	0.8421	0.056*
C4	0.41425 (18)	0.35955 (12)	0.78463 (11)	0.0459 (3)
C5	0.15402 (16)	0.58696 (10)	0.38503 (10)	0.0386 (3)
C6	0.05175 (18)	0.68231 (11)	0.33150 (11)	0.0439 (3)
H6	−0.0084	0.7452	0.3727	0.053*
C7	0.03742 (18)	0.68568 (11)	0.21824 (11)	0.0457 (3)
H7	−0.0314	0.7506	0.1838	0.055*
C8	0.12554 (18)	0.59239 (11)	0.15582 (10)	0.0444 (3)
C9	0.2264 (2)	0.49671 (12)	0.20906 (11)	0.0518 (4)
H9	0.286	0.4337	0.1677	0.062*
C10	0.24030 (19)	0.49303 (12)	0.32182 (11)	0.0487 (3)
H10	0.3076	0.4275	0.3561	0.058*
C11	0.0013 (2)	0.67727 (14)	−0.01187 (12)	0.0599 (4)
H11A	0.0047	0.6609	−0.0893	0.09*
H11B	0.0408	0.7488	−0.001	0.09*
H11C	−0.1233	0.6832	0.0171	0.09*
N1	0.16464 (14)	0.59247 (9)	0.50150 (8)	0.0406 (3)
H1N	0.1085	0.656	0.5312	0.049*
O1	0.33527 (15)	0.41551 (8)	0.53737 (8)	0.0625 (3)
O2	0.45825 (14)	0.29623 (8)	0.69728 (8)	0.0593 (3)
H2A	0.4196	0.3394	0.6353	0.089*
O3	0.45985 (15)	0.32053 (9)	0.87533 (8)	0.0644 (3)
O4	0.12243 (14)	0.58681 (9)	0.04387 (8)	0.0602 (3)
C21	0.22420 (17)	0.98092 (11)	0.13550 (10)	0.0415 (3)
C22	0.21905 (18)	0.94474 (11)	0.25224 (10)	0.0436 (3)
H22	0.2751	0.8685	0.2671	0.052*
C23	0.14486 (18)	1.00662 (12)	0.33956 (11)	0.0464 (3)
H23	0.1513	0.9648	0.4055	0.056*
C24	0.05379 (18)	1.13023 (12)	0.35040 (11)	0.0452 (3)
C25	0.33278 (16)	0.91072 (11)	−0.05093 (10)	0.0390 (3)
C26	0.40524 (19)	0.81103 (11)	−0.10879 (11)	0.0501 (3)
H26	0.4333	0.7409	−0.071	0.06*
C27	0.4366 (2)	0.81386 (12)	−0.22171 (11)	0.0512 (3)
H27	0.4853	0.7461	−0.2593	0.061*
C28	0.39523 (18)	0.91759 (11)	−0.27842 (10)	0.0448 (3)
C29	0.3238 (2)	1.01727 (12)	−0.22083 (11)	0.0528 (4)
H29	0.2962	1.0874	−0.2587	0.063*
C30	0.2928 (2)	1.01469 (12)	−0.10878 (11)	0.0503 (3)
H30	0.2448	1.0828	−0.0714	0.06*
C31	0.4932 (2)	0.83253 (14)	−0.45312 (12)	0.0605 (4)
H31A	0.5083	0.855	−0.5287	0.091*
H31B	0.4089	0.7801	−0.4484	0.091*
H31C	0.6116	0.7952	−0.4253	0.091*
N2	0.30677 (14)	0.90022 (9)	0.06518 (8)	0.0425 (3)
H2N	0.3498	0.8334	0.0934	0.051*
O5	0.15438 (16)	1.08043 (9)	0.10395 (8)	0.0675 (3)
O6	0.03939 (18)	1.19821 (9)	0.26512 (9)	0.0740 (4)
H6A	0.0815	1.156	0.203	0.111*
O7	−0.00459 (15)	1.16789 (9)	0.44012 (8)	0.0625 (3)
O8	0.42056 (16)	0.93176 (9)	−0.38950 (8)	0.0622 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0464 (7)	0.0308 (7)	0.0407 (7)	0.0016 (5)	0.0001 (5)	0.0018 (5)
C2	0.0502 (7)	0.0308 (7)	0.0424 (7)	0.0056 (5)	0.0015 (5)	0.0002 (6)
C3	0.0562 (8)	0.0393 (7)	0.0378 (7)	0.0058 (6)	−0.0007 (6)	−0.0002 (6)
C4	0.0510 (7)	0.0391 (7)	0.0426 (8)	0.0026 (6)	−0.0006 (6)	0.0064 (6)
C5	0.0423 (7)	0.0328 (7)	0.0381 (7)	−0.0017 (5)	0.0005 (5)	0.0024 (5)
C6	0.0551 (8)	0.0307 (7)	0.0415 (7)	0.0020 (6)	−0.0001 (6)	−0.0008 (6)
C7	0.0561 (8)	0.0318 (7)	0.0438 (8)	0.0038 (6)	−0.0042 (6)	0.0047 (6)
C8	0.0518 (8)	0.0410 (8)	0.0372 (7)	−0.0015 (6)	−0.0012 (6)	0.0007 (6)
C9	0.0604 (8)	0.0417 (8)	0.0436 (8)	0.0128 (6)	−0.0003 (6)	−0.0046 (6)
C10	0.0566 (8)	0.0375 (7)	0.0438 (8)	0.0101 (6)	−0.0027 (6)	0.0028 (6)
C11	0.0771 (10)	0.0557 (9)	0.0396 (8)	0.0045 (7)	−0.0068 (7)	0.0071 (7)
N1	0.0487 (6)	0.0303 (5)	0.0375 (6)	0.0045 (4)	0.0011 (4)	0.0013 (5)
O1	0.0925 (8)	0.0384 (6)	0.0427 (6)	0.0204 (5)	−0.0047 (5)	−0.0015 (4)
O2	0.0821 (7)	0.0365 (5)	0.0472 (6)	0.0170 (5)	−0.0037 (5)	0.0029 (5)
O3	0.0822 (7)	0.0526 (6)	0.0468 (6)	0.0141 (5)	−0.0062 (5)	0.0118 (5)
O4	0.0797 (7)	0.0535 (6)	0.0361 (5)	0.0137 (5)	−0.0050 (5)	−0.0008 (5)
C21	0.0456 (7)	0.0337 (7)	0.0403 (7)	0.0037 (5)	0.0009 (5)	−0.0005 (6)
C22	0.0523 (7)	0.0307 (7)	0.0420 (7)	0.0050 (5)	0.0017 (6)	0.0036 (6)
C23	0.0565 (8)	0.0392 (7)	0.0381 (7)	0.0026 (6)	0.0034 (6)	0.0050 (6)
C24	0.0504 (7)	0.0392 (7)	0.0413 (8)	0.0020 (6)	0.0032 (6)	−0.0032 (6)
C25	0.0416 (7)	0.0351 (7)	0.0369 (7)	0.0002 (5)	−0.0007 (5)	−0.0011 (5)
C26	0.0687 (9)	0.0329 (7)	0.0424 (8)	0.0043 (6)	0.0006 (6)	0.0018 (6)
C27	0.0699 (9)	0.0348 (7)	0.0429 (8)	0.0036 (6)	0.0022 (6)	−0.0081 (6)
C28	0.0552 (8)	0.0406 (8)	0.0367 (7)	−0.0048 (6)	−0.0002 (6)	−0.0021 (6)
C29	0.0748 (9)	0.0344 (7)	0.0436 (8)	0.0015 (6)	0.0044 (7)	0.0038 (6)
C30	0.0675 (9)	0.0332 (7)	0.0443 (8)	0.0030 (6)	0.0069 (6)	−0.0036 (6)
C31	0.0817 (10)	0.0549 (9)	0.0413 (8)	−0.0047 (8)	0.0054 (7)	−0.0117 (7)
N2	0.0533 (6)	0.0313 (6)	0.0375 (6)	0.0041 (5)	0.0010 (5)	0.0014 (5)
O5	0.1026 (8)	0.0409 (6)	0.0420 (6)	0.0240 (5)	0.0096 (5)	0.0054 (5)
O6	0.1190 (9)	0.0380 (6)	0.0475 (6)	0.0228 (6)	0.0169 (6)	0.0035 (5)
O7	0.0846 (7)	0.0484 (6)	0.0447 (6)	0.0092 (5)	0.0093 (5)	−0.0084 (5)
O8	0.0996 (8)	0.0456 (6)	0.0354 (5)	−0.0009 (5)	0.0053 (5)	−0.0028 (4)

C1—O1	1.2468 (15)	C21—O5	1.2444 (15)
C1—N1	1.3341 (16)	C21—N2	1.3295 (16)
C1—C2	1.4719 (18)	C21—C22	1.4735 (18)
C2—C3	1.3377 (18)	C22—C23	1.3353 (18)
C2—H2	0.93	C22—H22	0.93
C3—C4	1.4858 (18)	C23—C24	1.4862 (19)
C3—H3	0.93	C23—H23	0.93
C4—O3	1.2151 (16)	C24—O7	1.2151 (16)
C4—O2	1.3015 (16)	C24—O6	1.2930 (17)
C5—C6	1.3858 (17)	C25—C26	1.3845 (18)
C5—C10	1.3921 (18)	C25—C30	1.3890 (18)
C5—N1	1.4193 (16)	C25—N2	1.4217 (16)
C6—C7	1.3792 (18)	C26—C27	1.3824 (18)
C6—H6	0.93	C26—H26	0.93
C7—C8	1.3853 (19)	C27—C28	1.3803 (19)
C7—H7	0.93	C27—H27	0.93
C8—O4	1.3606 (16)	C28—O8	1.3662 (16)
C8—C9	1.3829 (19)	C28—C29	1.3812 (19)
C9—C10	1.3728 (19)	C29—C30	1.3715 (19)
C9—H9	0.93	C29—H29	0.93
C10—H10	0.93	C30—H30	0.93
C11—O4	1.4213 (17)	C31—O8	1.4174 (17)
C11—H11A	0.96	C31—H31A	0.96
C11—H11B	0.96	C31—H31B	0.96
C11—H11C	0.96	C31—H31C	0.96
N1—H1N	0.86	N2—H2N	0.86
O2—H2A	0.92	O6—H6A	0.92
O1—C1—N1	121.77 (12)	O5—C21—N2	121.73 (11)
O1—C1—C2	122.78 (12)	O5—C21—C22	122.37 (12)
N1—C1—C2	115.45 (11)	N2—C21—C22	115.89 (11)
C3—C2—C1	128.61 (12)	C23—C22—C21	128.78 (12)
C3—C2—H2	115.7	C23—C22—H22	115.6
C1—C2—H2	115.7	C21—C22—H22	115.6
C2—C3—C4	131.96 (13)	C22—C23—C24	131.60 (13)
C2—C3—H3	114	C22—C23—H23	114.2
C4—C3—H3	114	C24—C23—H23	114.2
O3—C4—O2	120.22 (12)	O7—C24—O6	119.93 (12)
O3—C4—C3	119.17 (13)	O7—C24—C23	119.81 (13)
O2—C4—C3	120.61 (11)	O6—C24—C23	120.25 (12)
C6—C5—C10	118.38 (12)	C26—C25—C30	118.52 (12)
C6—C5—N1	117.26 (11)	C26—C25—N2	117.52 (11)
C10—C5—N1	124.36 (11)	C30—C25—N2	123.95 (11)
C7—C6—C5	121.26 (12)	C27—C26—C25	121.19 (12)
C7—C6—H6	119.4	C27—C26—H26	119.4
C5—C6—H6	119.4	C25—C26—H26	119.4
C6—C7—C8	120.00 (12)	C28—C27—C26	119.77 (12)
C6—C7—H7	120	C28—C27—H27	120.1
C8—C7—H7	120	C26—C27—H27	120.1
O4—C8—C9	116.12 (12)	O8—C28—C27	125.33 (12)
O4—C8—C7	124.99 (12)	O8—C28—C29	115.50 (12)
C9—C8—C7	118.89 (12)	C27—C28—C29	119.17 (12)
C10—C9—C8	121.19 (13)	C30—C29—C28	121.17 (13)
C10—C9—H9	119.4	C30—C29—H29	119.4
C8—C9—H9	119.4	C28—C29—H29	119.4
C9—C10—C5	120.27 (12)	C29—C30—C25	120.18 (12)
C9—C10—H10	119.9	C29—C30—H30	119.9
C5—C10—H10	119.9	C25—C30—H30	119.9
O4—C11—H11A	109.5	O8—C31—H31A	109.5
O4—C11—H11B	109.5	O8—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
O4—C11—H11C	109.5	O8—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C1—N1—C5	128.19 (11)	C21—N2—C25	128.07 (11)
C1—N1—H1N	115.9	C21—N2—H2N	116
C5—N1—H1N	115.9	C25—N2—H2N	116
C4—O2—H2A	109.5	C24—O6—H6A	109.5
C8—O4—C11	117.28 (11)	C28—O8—C31	118.13 (11)
O1—C1—C2—C3	−1.0 (2)	O5—C21—C22—C23	−0.1 (2)
N1—C1—C2—C3	178.62 (13)	N2—C21—C22—C23	−179.46 (13)
C1—C2—C3—C4	−0.6 (2)	C21—C22—C23—C24	−3.5 (2)
C2—C3—C4—O3	−179.27 (15)	C22—C23—C24—O7	179.83 (14)
C2—C3—C4—O2	0.2 (2)	C22—C23—C24—O6	−1.4 (2)
C10—C5—C6—C7	−1.04 (19)	C30—C25—C26—C27	−0.4 (2)
N1—C5—C6—C7	178.47 (11)	N2—C25—C26—C27	−179.36 (12)
C5—C6—C7—C8	0.3 (2)	C25—C26—C27—C28	0.0 (2)
C6—C7—C8—O4	−179.29 (12)	C26—C27—C28—O8	179.68 (13)
C6—C7—C8—C9	0.3 (2)	C26—C27—C28—C29	0.3 (2)
O4—C8—C9—C10	179.56 (12)	O8—C28—C29—C30	−179.67 (12)
C7—C8—C9—C10	0.0 (2)	C27—C28—C29—C30	−0.2 (2)
C8—C9—C10—C5	−0.8 (2)	C28—C29—C30—C25	−0.1 (2)
C6—C5—C10—C9	1.27 (19)	C26—C25—C30—C29	0.4 (2)
N1—C5—C10—C9	−178.21 (12)	N2—C25—C30—C29	179.36 (12)
O1—C1—N1—C5	−0.7 (2)	O5—C21—N2—C25	1.0 (2)
C2—C1—N1—C5	179.61 (10)	C22—C21—N2—C25	−179.59 (11)
C6—C5—N1—C1	178.55 (12)	C26—C25—N2—C21	−173.12 (12)
C10—C5—N1—C1	−2.0 (2)	C30—C25—N2—C21	8.0 (2)
C9—C8—O4—C11	172.28 (13)	C27—C28—O8—C31	0.7 (2)
C7—C8—O4—C11	−8.2 (2)	C29—C28—O8—C31	−179.88 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.92	1.55	2.4624 (13)	174
O6—H6A···O5	0.92	1.53	2.4466 (14)	177
N1—H1N···O7i	0.86	2.10	2.9305 (14)	162
N2—H2N···O3ii	0.86	2.10	2.9124 (14)	158
C2—H2···O6i	0.93	2.44	3.3592 (16)	171
C6—H6···O7i	0.93	2.52	3.2822 (17)	140
C22—H22···O2ii	0.93	2.51	3.3792 (16)	156
C26—H26···O3ii	0.93	2.57	3.2881 (16)	135
C11—H11B···O5iii	0.96	2.56	3.0688 (18)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.92	1.55	2.4624 (13)	174
O6—H6A⋯O5	0.92	1.53	2.4466 (14)	177
N1—H1N⋯O7i	0.86	2.10	2.9305 (14)	162
N2—H2N⋯O3ii	0.86	2.10	2.9124 (14)	158
C2—H2⋯O6i	0.93	2.44	3.3592 (16)	171
C6—H6⋯O7i	0.93	2.52	3.2822 (17)	140
C22—H22⋯O2ii	0.93	2.51	3.3792 (16)	156
C26—H26⋯O3ii	0.93	2.57	3.2881 (16)	135
C11—H11B⋯O5iii	0.96	2.56	3.0688 (18)	113

Symmetry codes: (i) ; (ii) ; (iii) .