N-(p-Chloro­phenyl)­maleamic acid

The title mol­ecule, C₁₀H₈ClNO₃, is nearly planar, with the mean planes through the p-chloro­phenyl and maleamic acid groups inclined at an angle of 4.45 (1)° to each other. Symmetry-related mol­ecules are linked by N—H...O, C—H...O and C—H...Cl intermolecular hydrogen bonds, to form molecular 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 = 0.140
• Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_031  Alert C Refined Extinction Parameter within Range ....       3.00 Sigma


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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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-chlorophenyl)maleamic acid

Crystal data

C10H8ClNO3	F(000) = 464
Mr = 225.62	Dx = 1.513 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.306 (3) Å	θ = 8.2–18.9°
b = 11.765 (4) Å	µ = 0.37 mm^−1
c = 12.828 (4) Å	T = 293 K
β = 116.09 (4)°	Needle, light yellow
V = 990.3 (6) Å^3	0.25 × 0.23 × 0.10 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.5°
Graphite monochromator	h = 0→8
ω–2θ scans	k = 0→13
1707 measured reflections	l = −15→13
1707 independent reflections	3 standard reflections every 50 reflections
1224 reflections with I > 2σ(I)	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-atom parameters constrained
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.102P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
1707 reflections	Δρmax = 0.51 e Å^−3
137 parameters	Δρmin = −0.31 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: 0.006 (2)

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
Cl	0.26209 (14)	0.02180 (7)	0.35580 (7)	0.0632 (3)
C1	0.2566 (4)	0.1669 (3)	0.3758 (2)	0.0430 (7)
C2	0.2834 (5)	0.2104 (2)	0.4811 (2)	0.0475 (7)
H2	0.3028	0.1614	0.5420	0.057*
C3	0.2815 (4)	0.3263 (2)	0.4968 (2)	0.0436 (7)
H3	0.3009	0.3553	0.5684	0.052*
C4	0.2505 (4)	0.3999 (2)	0.4057 (2)	0.0375 (6)
C5	0.2257 (4)	0.3548 (2)	0.2996 (2)	0.0420 (7)
H5	0.2056	0.4030	0.2381	0.050*
C6	0.2310 (4)	0.2389 (2)	0.2861 (2)	0.0445 (7)
H6	0.2171	0.2092	0.2159	0.053*
C7	0.2406 (4)	0.5830 (2)	0.4987 (2)	0.0382 (6)
C8	0.2300 (4)	0.7058 (2)	0.4767 (2)	0.0391 (6)
H8	0.2189	0.7272	0.4044	0.047*
C9	0.2340 (4)	0.7909 (2)	0.5464 (2)	0.0426 (7)
H9	0.2231	0.8625	0.5134	0.051*
C10	0.2525 (4)	0.7936 (2)	0.6668 (2)	0.0421 (7)
N1	0.2435 (3)	0.51903 (19)	0.41304 (17)	0.0390 (6)
H1N	0.2408	0.5559	0.3545	0.047*
O1	0.2716 (3)	0.69932 (17)	0.72392 (16)	0.0566 (6)
H1O	0.2711	0.6453	0.6834	0.068*
O2	0.2541 (4)	0.88419 (17)	0.71042 (17)	0.0599 (6)
O3	0.2460 (3)	0.54096 (17)	0.58852 (16)	0.0551 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1002 (7)	0.0297 (4)	0.0585 (5)	−0.0022 (4)	0.0337 (5)	−0.0057 (3)
C1	0.0488 (16)	0.0319 (15)	0.0485 (16)	−0.0059 (12)	0.0216 (13)	−0.0069 (12)
C2	0.070 (2)	0.0366 (17)	0.0437 (15)	−0.0040 (14)	0.0319 (14)	0.0007 (12)
C3	0.0641 (18)	0.0388 (16)	0.0340 (13)	−0.0048 (13)	0.0272 (13)	−0.0029 (11)
C4	0.0465 (15)	0.0325 (14)	0.0347 (13)	−0.0043 (12)	0.0190 (11)	−0.0033 (11)
C5	0.0594 (17)	0.0378 (16)	0.0282 (13)	−0.0002 (13)	0.0187 (12)	0.0013 (11)
C6	0.0605 (19)	0.0385 (16)	0.0341 (13)	−0.0002 (13)	0.0205 (13)	−0.0068 (12)
C7	0.0498 (16)	0.0377 (16)	0.0300 (13)	−0.0029 (11)	0.0202 (12)	−0.0032 (11)
C8	0.0513 (16)	0.0364 (16)	0.0308 (13)	−0.0017 (12)	0.0192 (11)	−0.0017 (11)
C9	0.0633 (18)	0.0300 (15)	0.0379 (14)	0.0003 (12)	0.0254 (13)	0.0005 (11)
C10	0.0543 (17)	0.0336 (16)	0.0399 (14)	−0.0051 (12)	0.0223 (12)	−0.0091 (12)
N1	0.0561 (14)	0.0300 (12)	0.0322 (11)	−0.0029 (10)	0.0206 (10)	−0.0010 (9)
O1	0.1026 (17)	0.0362 (12)	0.0407 (10)	−0.0001 (10)	0.0404 (11)	−0.0030 (8)
O2	0.0986 (17)	0.0371 (12)	0.0528 (12)	−0.0055 (11)	0.0414 (12)	−0.0119 (10)
O3	0.0970 (17)	0.0362 (12)	0.0414 (11)	−0.0043 (10)	0.0391 (11)	−0.0025 (9)

Geometric parameters (Å, º)

Cl—C1	1.729 (3)	C7—O3	1.239 (3)
C1—C6	1.374 (4)	C7—N1	1.340 (3)
C1—C2	1.375 (4)	C7—C8	1.468 (4)
C2—C3	1.380 (4)	C8—C9	1.333 (4)
C2—H2	0.93	C8—H8	0.93
C3—C4	1.391 (4)	C9—C10	1.491 (4)
C3—H3	0.93	C9—H9	0.93
C4—C5	1.396 (4)	C10—O2	1.201 (3)
C4—N1	1.407 (4)	C10—O1	1.302 (3)
C5—C6	1.377 (4)	N1—H1N	0.86
C5—H5	0.93	O1—H1O	0.82
C6—H6	0.93
Cl···O1^i	3.121 (3)	C4···O2^iii	3.576 (3)
Cl···O3^i	3.458 (3)	C6···C8^iv	3.588 (4)
C2···C8^ii	3.494 (5)	C7···O3^v	3.538 (4)
C3···C8^ii	3.454 (5)	O3···O3^v	3.440 (3)
C6—C1—C2	120.1 (3)	C5—C6—H6	119.8
C6—C1—Cl	119.2 (2)	O3—C7—N1	122.2 (3)
C2—C1—Cl	120.7 (2)	O3—C7—C8	123.3 (2)
C1—C2—C3	120.3 (3)	N1—C7—C8	114.4 (2)
C1—C2—H2	119.8	C9—C8—C7	128.8 (2)
C3—C2—H2	119.8	C9—C8—H8	115.6
C2—C3—C4	120.1 (2)	C7—C8—H8	115.6
C2—C3—H3	120.0	C8—C9—C10	132.5 (2)
C4—C3—H3	120.0	C8—C9—H9	113.7
C3—C4—C5	119.1 (3)	C10—C9—H9	113.7
C3—C4—N1	124.1 (2)	O2—C10—O1	121.1 (2)
C5—C4—N1	116.8 (2)	O2—C10—C9	118.7 (2)
C6—C5—C4	120.0 (2)	O1—C10—C9	120.2 (2)
C6—C5—H5	120.0	C7—N1—C4	128.9 (2)
C4—C5—H5	120.0	C7—N1—H1N	115.5
C1—C6—C5	120.4 (2)	C4—N1—H1N	115.5
C1—C6—H6	119.8	C10—O1—H1O	109.5
C6—C1—C2—C3	1.0 (4)	O3—C7—C8—C9	3.5 (5)
Cl—C1—C2—C3	179.1 (2)	N1—C7—C8—C9	−176.7 (3)
C1—C2—C3—C4	0.6 (4)	C7—C8—C9—C10	0.9 (5)
C2—C3—C4—C5	−1.3 (4)	C8—C9—C10—O2	179.2 (3)
C2—C3—C4—N1	179.2 (3)	C8—C9—C10—O1	1.0 (5)
C3—C4—C5—C6	0.3 (4)	O3—C7—N1—C4	0.7 (4)
N1—C4—C5—C6	179.9 (3)	C8—C7—N1—C4	−179.1 (3)
C2—C1—C6—C5	−2.0 (4)	C3—C4—N1—C7	−8.4 (4)
Cl—C1—C6—C5	179.9 (2)	C5—C4—N1—C7	172.0 (3)
C4—C5—C6—C1	1.3 (4)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z−1/2; (iv) −x, y−1/2, −z+1/2; (v) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^iii	0.86	2.02	2.870 (3)	169
O1—H1O···O3	0.82	1.68	2.496 (3)	174
C3—H3···O3	0.93	2.26	2.847 (4)	121
C5—H5···O2^iii	0.93	2.58	3.315 (3)	137
C8—H8···O1^iii	0.93	2.65	3.567 (4)	168
C9—H9···Cl^vi	0.93	2.86	3.720 (3)	154

Symmetry codes: (iii) x, −y+3/2, z−1/2; (vi) x, y+1, z.