3-[(2,4,6-Tri­chloro­anilino)­carbonyl]­prop-2-enoic acid

The crystal structure of the title compound, C₁₀H₆Cl₃NO₃, establishes that condensation of 2,4,6-tri­chloro­aniline with maleic anhydride gives the title compound at room temperature. There are strong intermolecular N—H...O hydrogen bonds [N...O = 2.832 (2) and 2.867 (2) Å], resulting in a hydro­phobic region in the middle of the unit cell. The carboxyl groups adopt an anti-planar conformation and participate in intramolecular O—H...O hydrogen bonds [both O...O = 2.486 (2) Å]. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl5    ..  O1      ..       3.16 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3-[(2,4,6-Trichloroanilino)carbonyl]prop-2-enoic acid

Crystal data

C10H6Cl3NO3	Z = 4
Mr = 294.51	F(000) = 592
Triclinic, P1	Dx = 1.639 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.062 (1) Å	Cell parameters from 10295 reflections
b = 12.665 (2) Å	θ = 3.3–27.5°
c = 13.875 (3) Å	µ = 0.76 mm^−1
α = 98.372 (7)°	T = 173 K
β = 102.792 (8)°	Prism, colorless
γ = 92.732 (9)°	0.10 × 0.08 × 0.08 mm
V = 1193.2 (4) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	5428 independent reflections
Radiation source: fine-focus sealed tube	3762 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.928, Tmax = 0.942	k = −16→15
10295 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.16P] where P = (Fo^2 + 2Fc^2)/3
5428 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl1	0.32249 (8)	−0.17338 (5)	0.19859 (4)	0.05756 (18)
Cl2	−0.26885 (10)	−0.13183 (5)	−0.10711 (4)	0.06113 (19)
Cl3	−0.28011 (9)	0.04975 (4)	0.26538 (4)	0.05489 (17)
O1	0.3658 (2)	0.31959 (11)	0.63156 (11)	0.0510 (4)
O2	0.2432 (2)	0.29361 (11)	0.46975 (11)	0.0477 (4)
H1O	0.208 (3)	0.245 (2)	0.4182 (19)	0.057*
O3	0.1605 (3)	0.13332 (10)	0.33694 (10)	0.0520 (4)
N1	0.1040 (2)	−0.04464 (12)	0.32660 (12)	0.0343 (4)
H1N	0.114 (3)	−0.1016 (18)	0.3543 (16)	0.041*
C1	0.3028 (3)	0.25810 (14)	0.55428 (14)	0.0363 (4)
C2	0.2942 (3)	0.14136 (14)	0.55833 (14)	0.0365 (4)
H2	0.3352	0.1246	0.6239	0.044*
C3	0.2399 (3)	0.05580 (14)	0.48729 (14)	0.0347 (4)
H3	0.2498	−0.0118	0.5092	0.042*
C4	0.1662 (3)	0.05316 (14)	0.37867 (14)	0.0351 (4)
C5	0.0157 (3)	−0.06231 (13)	0.22257 (14)	0.0324 (4)
C6	0.1026 (3)	−0.12290 (15)	0.15519 (15)	0.0368 (4)
C7	0.0155 (3)	−0.14497 (16)	0.05339 (15)	0.0416 (5)
H7	0.0758	−0.1873	0.0083	0.050*
C8	−0.1593 (3)	−0.10430 (16)	0.01943 (15)	0.0423 (5)
C9	−0.2498 (3)	−0.04356 (16)	0.08412 (15)	0.0445 (5)
H9	−0.3709	−0.0160	0.0597	0.053*
C10	−0.1609 (3)	−0.02346 (14)	0.18522 (15)	0.0382 (5)
Cl4	0.20786 (10)	0.54345 (5)	0.19676 (5)	0.06137 (18)
Cl5	0.27323 (9)	0.32719 (4)	−0.15478 (4)	0.05137 (16)
Cl6	0.83176 (9)	0.31758 (5)	0.17480 (5)	0.06246 (18)
O4	0.8874 (2)	0.25018 (12)	0.61572 (13)	0.0574 (4)
O5	0.6925 (3)	0.20150 (11)	0.46722 (13)	0.0551 (4)
H5O	0.636 (4)	0.226 (2)	0.418 (2)	0.066*
O6	0.5608 (2)	0.29213 (10)	0.32217 (11)	0.0484 (4)
N2	0.5835 (3)	0.45790 (13)	0.28293 (12)	0.0388 (4)
H2N	0.608 (3)	0.5242 (19)	0.3070 (17)	0.047*
C11	0.7914 (3)	0.27493 (16)	0.53952 (17)	0.0425 (5)
C12	0.7825 (3)	0.39004 (15)	0.52980 (16)	0.0409 (5)
H12	0.8400	0.4378	0.5897	0.049*
C13	0.7088 (3)	0.43855 (14)	0.45247 (15)	0.0385 (5)
H13	0.7202	0.5146	0.4654	0.046*
C14	0.6111 (3)	0.38886 (14)	0.34875 (15)	0.0371 (4)
C15	0.5082 (3)	0.42438 (14)	0.17890 (14)	0.0362 (4)
C16	0.3343 (3)	0.45858 (15)	0.13008 (15)	0.0404 (5)
C17	0.2594 (3)	0.42843 (16)	0.02731 (16)	0.0437 (5)
H17	0.1396	0.4523	−0.0048	0.052*
C18	0.3628 (3)	0.36341 (15)	−0.02646 (15)	0.0409 (5)
C19	0.5366 (3)	0.32834 (16)	0.01881 (16)	0.0438 (5)
H19	0.6062	0.2833	−0.0194	0.053*
C20	0.6091 (3)	0.35946 (16)	0.12097 (16)	0.0407 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0479 (3)	0.0717 (4)	0.0452 (3)	0.0131 (3)	0.0057 (3)	−0.0112 (3)
Cl2	0.0865 (5)	0.0600 (4)	0.0269 (3)	−0.0126 (3)	−0.0048 (3)	0.0081 (2)
Cl3	0.0721 (4)	0.0477 (3)	0.0476 (3)	0.0246 (3)	0.0170 (3)	0.0054 (2)
O1	0.0808 (11)	0.0289 (7)	0.0342 (8)	−0.0026 (7)	0.0030 (8)	−0.0066 (6)
O2	0.0821 (11)	0.0240 (7)	0.0312 (8)	0.0005 (7)	0.0039 (7)	0.0012 (6)
O3	0.0965 (12)	0.0277 (7)	0.0265 (8)	−0.0097 (7)	0.0062 (8)	0.0038 (6)
N1	0.0518 (10)	0.0230 (8)	0.0253 (8)	0.0014 (7)	0.0052 (7)	0.0019 (6)
C1	0.0456 (11)	0.0284 (9)	0.0319 (11)	−0.0005 (8)	0.0078 (9)	−0.0016 (8)
C2	0.0484 (12)	0.0303 (10)	0.0276 (10)	0.0014 (8)	0.0026 (9)	0.0043 (8)
C3	0.0491 (12)	0.0246 (9)	0.0281 (10)	0.0009 (8)	0.0048 (9)	0.0042 (7)
C4	0.0498 (12)	0.0262 (9)	0.0273 (10)	−0.0012 (8)	0.0082 (9)	0.0009 (8)
C5	0.0474 (11)	0.0228 (9)	0.0249 (10)	−0.0037 (8)	0.0066 (8)	0.0012 (7)
C6	0.0418 (11)	0.0330 (10)	0.0323 (11)	−0.0035 (8)	0.0069 (9)	−0.0008 (8)
C7	0.0550 (13)	0.0382 (11)	0.0282 (11)	−0.0081 (9)	0.0107 (9)	−0.0037 (8)
C8	0.0599 (14)	0.0357 (10)	0.0259 (10)	−0.0095 (9)	0.0012 (9)	0.0052 (8)
C9	0.0551 (13)	0.0403 (11)	0.0348 (12)	0.0039 (9)	0.0001 (10)	0.0106 (9)
C10	0.0540 (12)	0.0274 (10)	0.0332 (11)	0.0050 (8)	0.0100 (9)	0.0046 (8)
Cl4	0.0734 (4)	0.0601 (4)	0.0464 (4)	0.0235 (3)	0.0121 (3)	−0.0081 (3)
Cl5	0.0722 (4)	0.0482 (3)	0.0296 (3)	−0.0079 (3)	0.0096 (3)	0.0002 (2)
Cl6	0.0576 (4)	0.0807 (4)	0.0479 (4)	0.0185 (3)	0.0120 (3)	0.0025 (3)
O4	0.0743 (11)	0.0463 (9)	0.0566 (10)	0.0168 (8)	0.0131 (9)	0.0243 (8)
O5	0.0949 (13)	0.0260 (7)	0.0477 (10)	0.0075 (8)	0.0205 (9)	0.0097 (7)
O6	0.0810 (11)	0.0235 (7)	0.0387 (8)	−0.0059 (7)	0.0148 (8)	−0.0002 (6)
N2	0.0603 (11)	0.0224 (8)	0.0309 (9)	−0.0010 (7)	0.0081 (8)	0.0006 (7)
C11	0.0546 (13)	0.0357 (11)	0.0461 (13)	0.0124 (9)	0.0241 (11)	0.0134 (10)
C12	0.0591 (13)	0.0281 (10)	0.0354 (11)	0.0060 (9)	0.0113 (10)	0.0038 (8)
C13	0.0556 (12)	0.0230 (9)	0.0357 (11)	0.0029 (8)	0.0104 (9)	0.0014 (8)
C14	0.0521 (12)	0.0266 (10)	0.0338 (11)	0.0025 (8)	0.0141 (9)	0.0027 (8)
C15	0.0525 (12)	0.0250 (9)	0.0300 (11)	−0.0049 (8)	0.0110 (9)	0.0014 (8)
C16	0.0572 (13)	0.0297 (10)	0.0346 (11)	0.0032 (9)	0.0145 (10)	0.0009 (8)
C17	0.0533 (13)	0.0375 (11)	0.0375 (12)	0.0001 (9)	0.0063 (10)	0.0050 (9)
C18	0.0585 (13)	0.0337 (10)	0.0283 (11)	−0.0092 (9)	0.0106 (9)	0.0011 (8)
C19	0.0563 (13)	0.0400 (11)	0.0357 (12)	−0.0007 (9)	0.0171 (10)	−0.0005 (9)
C20	0.0488 (12)	0.0370 (11)	0.0373 (12)	−0.0008 (9)	0.0134 (9)	0.0049 (9)

Geometric parameters (Å, º)

Cl1—C6	1.725 (2)	Cl4—C16	1.725 (2)
Cl2—C8	1.731 (2)	Cl5—C18	1.737 (2)
Cl3—C10	1.730 (2)	Cl6—C20	1.728 (2)
O1—C1	1.211 (2)	O4—C11	1.215 (3)
O2—C1	1.307 (2)	O5—C11	1.310 (3)
O2—H1O	0.86 (2)	O5—H5O	0.83 (3)
O3—C4	1.238 (2)	O6—C14	1.238 (2)
N1—C4	1.340 (2)	N2—C14	1.344 (3)
N1—C5	1.420 (2)	N2—C15	1.416 (2)
N1—H1N	0.86 (2)	N2—H2N	0.85 (2)
C1—C2	1.487 (3)	C11—C12	1.487 (3)
C2—C3	1.332 (3)	C12—C13	1.332 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.476 (3)	C13—C14	1.483 (3)
C3—H3	0.9500	C13—H13	0.9500
C5—C10	1.383 (3)	C15—C16	1.387 (3)
C5—C6	1.389 (3)	C15—C20	1.395 (3)
C6—C7	1.391 (3)	C16—C17	1.395 (3)
C7—C8	1.373 (3)	C17—C18	1.374 (3)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.380 (3)	C18—C19	1.375 (3)
C9—C10	1.385 (3)	C19—C20	1.387 (3)
C9—H9	0.9500	C19—H19	0.9500
C1—O2—H1O	114.6 (17)	C11—O5—H5O	113.6 (19)
C4—N1—C5	122.71 (16)	C14—N2—C15	122.62 (16)
C4—N1—H1N	122.2 (14)	C14—N2—H2N	116.6 (15)
C5—N1—H1N	115.1 (14)	C15—N2—H2N	120.7 (15)
O1—C1—O2	120.79 (18)	O4—C11—O5	120.68 (19)
O1—C1—C2	118.22 (18)	O4—C11—C12	119.4 (2)
O2—C1—C2	120.99 (16)	O5—C11—C12	119.9 (2)
C3—C2—C1	132.10 (18)	C13—C12—C11	131.8 (2)
C3—C2—H2	113.9	C13—C12—H12	114.1
C1—C2—H2	113.9	C11—C12—H12	114.1
C2—C3—C4	127.96 (17)	C12—C13—C14	128.21 (18)
C2—C3—H3	116.0	C12—C13—H13	115.9
C4—C3—H3	116.0	C14—C13—H13	115.9
O3—C4—N1	121.34 (18)	O6—C14—N2	121.34 (18)
O3—C4—C3	124.10 (16)	O6—C14—C13	124.36 (18)
N1—C4—C3	114.55 (16)	N2—C14—C13	114.28 (16)
C10—C5—C6	117.82 (17)	C16—C15—C20	117.45 (18)
C10—C5—N1	121.75 (17)	C16—C15—N2	120.93 (18)
C6—C5—N1	120.40 (18)	C20—C15—N2	121.57 (19)
C5—C6—C7	121.61 (19)	C15—C16—C17	121.94 (19)
C5—C6—Cl1	119.38 (15)	C15—C16—Cl4	119.62 (15)
C7—C6—Cl1	119.01 (16)	C17—C16—Cl4	118.42 (17)
C8—C7—C6	118.64 (19)	C18—C17—C16	118.5 (2)
C8—C7—H7	120.7	C18—C17—H17	120.7
C6—C7—H7	120.7	C16—C17—H17	120.7
C7—C8—C9	121.39 (18)	C17—C18—C19	121.44 (19)
C7—C8—Cl2	118.89 (17)	C17—C18—Cl5	118.95 (18)
C9—C8—Cl2	119.72 (17)	C19—C18—Cl5	119.59 (17)
C8—C9—C10	118.9 (2)	C18—C19—C20	119.2 (2)
C8—C9—H9	120.6	C18—C19—H19	120.4
C10—C9—H9	120.6	C20—C19—H19	120.4
C5—C10—C9	121.68 (19)	C19—C20—C15	121.4 (2)
C5—C10—Cl3	120.25 (15)	C19—C20—Cl6	118.03 (17)
C9—C10—Cl3	118.06 (17)	C15—C20—Cl6	120.54 (16)
O1—C1—C2—C3	−177.4 (2)	O4—C11—C12—C13	171.4 (2)
O2—C1—C2—C3	2.9 (3)	O5—C11—C12—C13	−10.2 (4)
C1—C2—C3—C4	−1.0 (4)	C11—C12—C13—C14	−0.6 (4)
C5—N1—C4—O3	−4.5 (3)	C15—N2—C14—O6	−4.4 (3)
C5—N1—C4—C3	175.49 (17)	C15—N2—C14—C13	174.37 (18)
C2—C3—C4—O3	6.5 (3)	C12—C13—C14—O6	10.1 (4)
C2—C3—C4—N1	−173.5 (2)	C12—C13—C14—N2	−168.6 (2)
C4—N1—C5—C10	−64.6 (3)	C14—N2—C15—C16	118.5 (2)
C4—N1—C5—C6	117.6 (2)	C14—N2—C15—C20	−64.1 (3)
C10—C5—C6—C7	−0.4 (3)	C20—C15—C16—C17	1.1 (3)
N1—C5—C6—C7	177.46 (16)	N2—C15—C16—C17	178.62 (17)
C10—C5—C6—Cl1	−179.75 (14)	C20—C15—C16—Cl4	−177.37 (15)
N1—C5—C6—Cl1	−1.9 (2)	N2—C15—C16—Cl4	0.2 (3)
C5—C6—C7—C8	0.8 (3)	C15—C16—C17—C18	−0.4 (3)
Cl1—C6—C7—C8	−179.86 (15)	Cl4—C16—C17—C18	178.09 (15)
C6—C7—C8—C9	−0.7 (3)	C16—C17—C18—C19	−0.1 (3)
C6—C7—C8—Cl2	−179.78 (14)	C16—C17—C18—Cl5	−178.91 (14)
C7—C8—C9—C10	0.2 (3)	C17—C18—C19—C20	−0.1 (3)
Cl2—C8—C9—C10	179.26 (15)	Cl5—C18—C19—C20	178.67 (15)
C6—C5—C10—C9	−0.1 (3)	C18—C19—C20—C15	0.9 (3)
N1—C5—C10—C9	−177.97 (17)	C18—C19—C20—Cl6	−177.91 (15)
C6—C5—C10—Cl3	178.37 (14)	C16—C15—C20—C19	−1.3 (3)
N1—C5—C10—Cl3	0.5 (2)	N2—C15—C20—C19	−178.84 (17)
C8—C9—C10—C5	0.3 (3)	C16—C15—C20—Cl6	177.41 (14)
C8—C9—C10—Cl3	−178.26 (15)	N2—C15—C20—Cl6	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···O3	0.86 (2)	1.64 (3)	2.486 (2)	167 (2)
N1—H1N···O4^i	0.86 (2)	1.99 (2)	2.832 (2)	166 (2)
O5—H5O···O6	0.83 (3)	1.67 (3)	2.486 (2)	169 (3)
N2—H2N···O1^ii	0.85 (2)	2.02 (2)	2.867 (2)	173 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.