N-(2,5-Dichloro-phen-yl)maleamic acid.

The asymmetric unit of the title compound, C(10)H(7)Cl(2)NO(3), contains two independent mol-ecules. The mol-ecular conformation of each maleamic unit is stabilized by an intra-molecular O-H⋯O(carbon-yl) hydrogen bond owing to the anti disposition of the participating entities. The mean planes through the benzene ring and the amido group are inclined at angles of 45.7 (1) and 40.8 (1)° in the two mol-ecules. In the crystal, the independent mol-ecules self-associate via N-H⋯O hydrogen bonds into zigzag ribbons propagating along the a axis. The ribbons are weakly coupled by C-H⋯π and C-H⋯O inter-actions.

Related literature

For related structures, see: Gowda, Foro et al. (2009 ▶); Gowda, Tokarčík et al. (2009 ▶); Leiserowitz (1976 ▶); Lo & Ng (2009 ▶); Prasad et al. (2002 ▶).

Experimental

Crystal data

C10H7Cl2NO3

M = 260.07

Orthorhombic,

a = 13.1618 (2) Å

b = 14.6993 (2) Å

c = 22.8406 (3) Å

V = 4418.95 (11) Å3

Z = 16

Mo Kα radiation

μ = 0.58 mm−1

T = 295 K

0.40 × 0.33 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical (CrysAlis Pro ; Oxford Diffraction, 2009 ▶) T min = 0.836, T max = 0.892

61823 measured reflections

4191 independent reflections

3514 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.08

4191 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 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/S1600536809048715/tk2578sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048715/tk2578Isup2.hkl

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

C10H7Cl2NO3	F(000) = 2112
Mr = 260.07	Dx = 1.564 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 31107 reflections
a = 13.1618 (2) Å	θ = 1.6–29.5°
b = 14.6993 (2) Å	µ = 0.58 mm−1
c = 22.8406 (3) Å	T = 295 K
V = 4418.95 (11) Å3	Block, colourless
Z = 16	0.40 × 0.33 × 0.24 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4191 independent reflections
graphite	3514 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.029
ω scans	θmax = 25.7°, θmin = 2.3°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −16→16
Tmin = 0.836, Tmax = 0.892	k = −17→17
61823 measured reflections	l = −27→27

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.705P] where P = (Fo2 + 2Fc2)/3
4191 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.25 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	0.73471 (10)	−0.00911 (10)	0.32684 (6)	0.0350 (3)
C2	0.72297 (11)	−0.04413 (10)	0.26641 (7)	0.0415 (3)
H2	0.6567	−0.0563	0.2547	0.05*
C3	0.79490 (12)	−0.06048 (11)	0.22658 (7)	0.0441 (4)
H3	0.7699	−0.0823	0.1912	0.053*
C4	0.90735 (12)	−0.05043 (11)	0.22796 (7)	0.0441 (4)
C5	0.63841 (10)	0.02870 (9)	0.41515 (6)	0.0339 (3)
C6	0.56221 (11)	0.08972 (9)	0.43094 (6)	0.0364 (3)
C7	0.54753 (12)	0.11305 (10)	0.48908 (7)	0.0415 (3)
H7	0.4961	0.1535	0.4992	0.05*
C8	0.60896 (11)	0.07648 (10)	0.53206 (7)	0.0416 (3)
H8	0.5994	0.0918	0.5712	0.05*
C9	0.68479 (11)	0.01675 (10)	0.51585 (6)	0.0374 (3)
C10	0.70068 (11)	−0.00722 (10)	0.45830 (6)	0.0363 (3)
H10	0.7527	−0.0472	0.4485	0.044*
N1	0.64725 (9)	0.00060 (8)	0.35603 (5)	0.0376 (3)
H1N	0.592	−0.0112	0.3374	0.045*
O1	0.81770 (8)	0.01020 (8)	0.34893 (4)	0.0466 (3)
O2	0.95290 (9)	−0.01830 (9)	0.27441 (5)	0.0616 (3)
H2A	0.9105	−0.0062	0.2995	0.092*
O3	0.95614 (9)	−0.07270 (9)	0.18517 (5)	0.0602 (3)
Cl1	0.48365 (3)	0.13629 (3)	0.378143 (19)	0.05137 (12)
Cl2	0.76232 (3)	−0.03099 (3)	0.569340 (18)	0.05382 (13)
C11	0.54290 (10)	0.29825 (10)	0.65172 (6)	0.0359 (3)
C12	0.55854 (11)	0.30418 (11)	0.71586 (6)	0.0415 (4)
H12	0.4998	0.3071	0.7384	0.05*
C13	0.64578 (11)	0.30582 (11)	0.74530 (6)	0.0420 (3)
H13	0.6379	0.31	0.7857	0.05*
C14	0.75294 (11)	0.30223 (11)	0.72582 (7)	0.0410 (3)
C15	0.41539 (10)	0.31099 (9)	0.57492 (6)	0.0349 (3)
C16	0.32356 (11)	0.27102 (9)	0.55905 (7)	0.0366 (3)
C17	0.29294 (12)	0.26877 (10)	0.50117 (7)	0.0444 (4)
H17	0.2322	0.2405	0.491	0.053*
C18	0.35224 (13)	0.30829 (11)	0.45862 (7)	0.0471 (4)
H18	0.3326	0.3062	0.4195	0.057*
C19	0.44124 (12)	0.35108 (10)	0.47466 (7)	0.0423 (4)
C20	0.47341 (11)	0.35263 (10)	0.53203 (7)	0.0397 (3)
H20	0.5339	0.3815	0.5419	0.048*
N2	0.44678 (9)	0.31040 (9)	0.63412 (5)	0.0386 (3)
H2N	0.4011	0.3184	0.6606	0.046*
O4	0.61248 (8)	0.28343 (8)	0.61652 (4)	0.0496 (3)
O5	0.77523 (8)	0.28321 (10)	0.67163 (5)	0.0590 (3)
H5A	0.7227	0.2744	0.6532	0.089*
O6	0.81990 (9)	0.31650 (10)	0.76074 (6)	0.0696 (4)
Cl3	0.24556 (3)	0.22391 (3)	0.61215 (2)	0.05196 (12)
Cl4	0.51489 (4)	0.40468 (4)	0.42195 (2)	0.06528 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0294 (8)	0.0400 (8)	0.0355 (8)	0.0015 (6)	0.0014 (6)	0.0035 (6)
C2	0.0301 (8)	0.0553 (9)	0.0390 (8)	−0.0023 (6)	−0.0013 (6)	−0.0030 (7)
C3	0.0413 (8)	0.0563 (9)	0.0347 (8)	−0.0033 (7)	0.0042 (7)	−0.0038 (7)
C4	0.0385 (8)	0.0509 (9)	0.0431 (9)	0.0007 (7)	0.0099 (7)	0.0071 (7)
C5	0.0272 (7)	0.0384 (7)	0.0362 (7)	0.0001 (6)	0.0043 (6)	−0.0015 (6)
C6	0.0296 (7)	0.0363 (7)	0.0434 (8)	0.0015 (6)	0.0032 (6)	0.0027 (6)
C7	0.0366 (8)	0.0384 (8)	0.0494 (9)	0.0028 (6)	0.0099 (7)	−0.0059 (7)
C8	0.0443 (8)	0.0428 (8)	0.0376 (8)	−0.0030 (7)	0.0086 (7)	−0.0067 (6)
C9	0.0365 (8)	0.0389 (8)	0.0369 (8)	−0.0043 (6)	0.0000 (6)	0.0017 (6)
C10	0.0303 (7)	0.0398 (8)	0.0390 (8)	0.0046 (6)	0.0033 (6)	−0.0005 (6)
N1	0.0269 (6)	0.0513 (7)	0.0346 (6)	0.0040 (5)	−0.0002 (5)	−0.0021 (5)
O1	0.0311 (6)	0.0708 (7)	0.0381 (6)	−0.0067 (5)	0.0014 (5)	−0.0048 (5)
O2	0.0323 (6)	0.1000 (10)	0.0524 (7)	−0.0044 (6)	0.0077 (5)	−0.0069 (7)
O3	0.0476 (7)	0.0808 (9)	0.0523 (7)	−0.0011 (6)	0.0219 (6)	−0.0027 (6)
Cl1	0.0399 (2)	0.0602 (3)	0.0540 (2)	0.01679 (18)	−0.00180 (18)	0.00427 (19)
Cl2	0.0543 (3)	0.0671 (3)	0.0401 (2)	0.0055 (2)	−0.00553 (18)	0.00738 (18)
C11	0.0255 (7)	0.0469 (8)	0.0352 (8)	−0.0010 (6)	−0.0001 (6)	−0.0043 (6)
C12	0.0253 (7)	0.0661 (10)	0.0331 (8)	0.0018 (7)	0.0046 (6)	−0.0053 (7)
C13	0.0325 (8)	0.0634 (9)	0.0300 (7)	0.0007 (7)	0.0005 (6)	−0.0079 (7)
C14	0.0284 (7)	0.0562 (9)	0.0385 (8)	−0.0011 (6)	−0.0045 (7)	0.0018 (7)
C15	0.0275 (7)	0.0399 (8)	0.0371 (8)	0.0039 (6)	−0.0037 (6)	−0.0061 (6)
C16	0.0295 (7)	0.0344 (7)	0.0460 (8)	0.0021 (6)	−0.0031 (6)	−0.0047 (6)
C17	0.0375 (8)	0.0430 (9)	0.0528 (10)	0.0028 (7)	−0.0152 (7)	−0.0104 (7)
C18	0.0519 (10)	0.0502 (9)	0.0393 (8)	0.0115 (8)	−0.0133 (7)	−0.0074 (7)
C19	0.0418 (9)	0.0452 (8)	0.0398 (8)	0.0119 (7)	0.0017 (7)	0.0013 (7)
C20	0.0309 (8)	0.0447 (8)	0.0435 (9)	0.0003 (6)	−0.0019 (6)	−0.0039 (7)
N2	0.0242 (6)	0.0577 (8)	0.0339 (6)	0.0000 (5)	0.0004 (5)	−0.0058 (5)
O4	0.0305 (6)	0.0850 (8)	0.0334 (5)	0.0094 (5)	0.0014 (5)	−0.0056 (5)
O5	0.0273 (6)	0.1095 (10)	0.0403 (6)	0.0074 (6)	0.0025 (5)	−0.0009 (6)
O6	0.0334 (6)	0.1215 (11)	0.0539 (7)	−0.0072 (7)	−0.0134 (6)	−0.0058 (7)
Cl3	0.0386 (2)	0.0552 (3)	0.0621 (3)	−0.01198 (17)	0.00285 (18)	−0.00156 (19)
Cl4	0.0633 (3)	0.0810 (3)	0.0515 (3)	0.0115 (2)	0.0144 (2)	0.0150 (2)

C1—O1	1.2364 (17)	C11—O4	1.2380 (17)
C1—N1	1.3378 (18)	C11—N2	1.3395 (18)
C1—C2	1.481 (2)	C11—C12	1.482 (2)
C2—C3	1.335 (2)	C12—C13	1.331 (2)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.488 (2)	C13—C14	1.480 (2)
C3—H3	0.93	C13—H13	0.93
C4—O3	1.2143 (19)	C14—O6	1.2070 (19)
C4—O2	1.307 (2)	C14—O5	1.3024 (19)
C5—C10	1.386 (2)	C15—C20	1.385 (2)
C5—C6	1.3931 (19)	C15—C16	1.392 (2)
C5—N1	1.4168 (18)	C15—N2	1.4141 (18)
C6—C7	1.385 (2)	C16—C17	1.382 (2)
C6—Cl1	1.7298 (15)	C16—Cl3	1.7334 (15)
C7—C8	1.381 (2)	C17—C18	1.375 (2)
C7—H7	0.93	C17—H17	0.93
C8—C9	1.380 (2)	C18—C19	1.379 (2)
C8—H8	0.93	C18—H18	0.93
C9—C10	1.377 (2)	C19—C20	1.377 (2)
C9—Cl2	1.7397 (15)	C19—Cl4	1.7349 (16)
C10—H10	0.93	C20—H20	0.93
N1—H1N	0.86	N2—H2N	0.86
O2—H2A	0.82	O5—H5A	0.82
O1—C1—N1	122.16 (13)	O4—C11—N2	121.82 (13)
O1—C1—C2	123.52 (13)	O4—C11—C12	123.35 (13)
N1—C1—C2	114.32 (13)	N2—C11—C12	114.83 (12)
C3—C2—C1	128.59 (14)	C13—C12—C11	128.35 (13)
C3—C2—H2	115.7	C13—C12—H12	115.8
C1—C2—H2	115.7	C11—C12—H12	115.8
C2—C3—C4	132.31 (15)	C12—C13—C14	132.04 (14)
C2—C3—H3	113.8	C12—C13—H13	114
C4—C3—H3	113.8	C14—C13—H13	114
O3—C4—O2	120.55 (15)	O6—C14—O5	120.06 (14)
O3—C4—C3	118.83 (15)	O6—C14—C13	119.40 (14)
O2—C4—C3	120.62 (13)	O5—C14—C13	120.54 (13)
C10—C5—C6	119.12 (13)	C20—C15—C16	118.76 (13)
C10—C5—N1	121.19 (12)	C20—C15—N2	121.22 (13)
C6—C5—N1	119.59 (13)	C16—C15—N2	120.01 (13)
C7—C6—C5	120.54 (14)	C17—C16—C15	120.82 (14)
C7—C6—Cl1	119.15 (11)	C17—C16—Cl3	119.13 (12)
C5—C6—Cl1	120.30 (11)	C15—C16—Cl3	120.05 (11)
C8—C7—C6	120.24 (14)	C18—C17—C16	120.01 (14)
C8—C7—H7	119.9	C18—C17—H17	120
C6—C7—H7	119.9	C16—C17—H17	120
C9—C8—C7	118.71 (14)	C17—C18—C19	119.13 (14)
C9—C8—H8	120.6	C17—C18—H18	120.4
C7—C8—H8	120.6	C19—C18—H18	120.4
C10—C9—C8	121.93 (14)	C20—C19—C18	121.43 (15)
C10—C9—Cl2	118.56 (11)	C20—C19—Cl4	118.75 (13)
C8—C9—Cl2	119.50 (11)	C18—C19—Cl4	119.82 (12)
C9—C10—C5	119.44 (13)	C19—C20—C15	119.76 (14)
C9—C10—H10	120.3	C19—C20—H20	120.1
C5—C10—H10	120.3	C15—C20—H20	120.1
C1—N1—C5	125.22 (12)	C11—N2—C15	124.31 (12)
C1—N1—H1N	117.4	C11—N2—H2N	117.8
C5—N1—H1N	117.4	C15—N2—H2N	117.8
C4—O2—H2A	109.5	C14—O5—H5A	109.5
O1—C1—C2—C3	−0.1 (3)	O4—C11—C12—C13	8.6 (3)
N1—C1—C2—C3	179.57 (16)	N2—C11—C12—C13	−171.30 (16)
C1—C2—C3—C4	0.2 (3)	C11—C12—C13—C14	−0.2 (3)
C2—C3—C4—O3	178.25 (18)	C12—C13—C14—O6	170.54 (18)
C2—C3—C4—O2	−1.7 (3)	C12—C13—C14—O5	−10.0 (3)
C10—C5—C6—C7	−1.1 (2)	C20—C15—C16—C17	3.2 (2)
N1—C5—C6—C7	175.32 (13)	N2—C15—C16—C17	−178.24 (13)
C10—C5—C6—Cl1	179.64 (11)	C20—C15—C16—Cl3	−176.38 (11)
N1—C5—C6—Cl1	−3.89 (19)	N2—C15—C16—Cl3	2.19 (18)
C5—C6—C7—C8	0.5 (2)	C15—C16—C17—C18	−1.6 (2)
Cl1—C6—C7—C8	179.72 (11)	Cl3—C16—C17—C18	177.97 (11)
C6—C7—C8—C9	0.1 (2)	C16—C17—C18—C19	−1.0 (2)
C7—C8—C9—C10	0.0 (2)	C17—C18—C19—C20	2.0 (2)
C7—C8—C9—Cl2	−179.39 (11)	C17—C18—C19—Cl4	−177.81 (12)
C8—C9—C10—C5	−0.6 (2)	C18—C19—C20—C15	−0.4 (2)
Cl2—C9—C10—C5	178.73 (11)	Cl4—C19—C20—C15	179.43 (11)
C6—C5—C10—C9	1.2 (2)	C16—C15—C20—C19	−2.2 (2)
N1—C5—C10—C9	−175.21 (13)	N2—C15—C20—C19	179.26 (13)
O1—C1—N1—C5	−3.4 (2)	O4—C11—N2—C15	−2.4 (2)
C2—C1—N1—C5	176.88 (13)	C12—C11—N2—C15	177.50 (13)
C10—C5—N1—C1	−45.1 (2)	C20—C15—N2—C11	−39.9 (2)
C6—C5—N1—C1	138.55 (15)	C16—C15—N2—C11	141.55 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86	2.07	2.8938 (17)	160
N2—H2N···O6ii	0.86	2.09	2.9263 (17)	164
O2—H2A···O1	0.82	1.68	2.4979 (15)	175
O5—H5A···O4	0.82	1.68	2.4846 (15)	166
C7—H7···Cg2	0.93	2.77	3.6745 (15)	163
C18—H18···O5iii	0.93	2.58	3.4186 (19)	151
C20—H20···O4	0.93	2.46	2.8477 (18)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86	2.07	2.8938 (17)	160
N2—H2N⋯O6ii	0.86	2.09	2.9263 (17)	164
O2—H2A⋯O1	0.82	1.68	2.4979 (15)	175
O5—H5A⋯O4	0.82	1.68	2.4846 (15)	166
C7—H7⋯Cg2	0.93	2.77	3.6745 (15)	163
C18—H18⋯O5iii	0.93	2.58	3.4186 (19)	151

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the C15–C20 ring.