3-[(4-Bromo­anilino)­carbonyl]­prop-2-enoic acid

The crystal structure of the title compound, C₁₀H₈BrNO₃, establishes that condensation of 4-bromo­aniline with maleic anhydride gives the title compound at room temperature. There are strong intermolecular N—H...O hydrogen bonds [N...O = 2.814 (3) Å and 2.817 (3) Å] linking the mol­ecules into sheets lying parallel to the bc plane. The carboxyl groups adopt an anti-planar conformation and participate in intramolecular O—H...O hydrogen bonds [O...O = 2.484 (3) and 2.487 (3) Å]. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.034
• wR factor = 0.083
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.09
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.02

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

   0 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 (Sheldrick, 1997).

3-[(4-Bromoanilino)carbonyl]prop-2-enoic acid

Crystal data

C10H8BrNO3	Z = 4
Mr = 270.08	F(000) = 536
Triclinic, P1	Dx = 1.765 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.481 (2) Å	Cell parameters from 8520 reflections
b = 10.844 (2) Å	θ = 2.2–27.5°
c = 11.151 (3) Å	µ = 4.03 mm^−1
α = 106.576 (9)°	T = 173 K
β = 106.92 (1)°	Block, colorless
γ = 111.192 (10)°	0.12 × 0.12 × 0.08 mm
V = 1016.4 (4) Å^3

Data collection

Nonius KappaCCD diffractometer	4621 independent reflections
Radiation source: fine-focus sealed tube	3578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −13→13
Tmin = 0.631, Tmax = 0.724	k = −14→14
8520 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
4621 reflections	(Δ/σ)max = 0.002
283 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	−0.09526 (3)	−0.37381 (3)	0.02809 (3)	0.03827 (10)
Br2	0.15455 (3)	−0.08396 (3)	0.45786 (3)	0.04470 (11)
O1	1.1215 (2)	0.4763 (2)	0.3944 (2)	0.0481 (5)
O2	0.9492 (2)	0.2777 (2)	0.3823 (2)	0.0411 (5)
H2O	0.844 (4)	0.216 (4)	0.338 (4)	0.062*
O3	0.66633 (19)	0.1312 (2)	0.25669 (19)	0.0352 (4)
O4	0.6359 (2)	0.7790 (2)	0.1033 (2)	0.0413 (5)
O5	0.4486 (2)	0.5980 (2)	0.0987 (2)	0.0430 (5)
H5O	0.430 (4)	0.546 (4)	0.142 (4)	0.065*
O6	0.4306 (2)	0.4430 (2)	0.2261 (2)	0.0419 (5)
N1	0.4707 (2)	0.1248 (2)	0.0948 (2)	0.0227 (4)
H1N	0.444 (3)	0.155 (3)	0.032 (3)	0.027*
N2	0.5855 (2)	0.4274 (2)	0.4035 (2)	0.0253 (4)
H2N	0.672 (3)	0.457 (3)	0.456 (3)	0.030*
C1	0.9883 (3)	0.3832 (3)	0.3439 (3)	0.0304 (6)
C2	0.8730 (3)	0.3917 (3)	0.2367 (3)	0.0274 (5)
H2	0.9151	0.4700	0.2135	0.033*
C3	0.7212 (3)	0.3105 (2)	0.1664 (2)	0.0241 (5)
H3	0.6726	0.3387	0.1014	0.029*
C4	0.6193 (3)	0.1818 (3)	0.1773 (2)	0.0224 (5)
C5	0.3444 (3)	0.0057 (2)	0.0829 (2)	0.0219 (5)
C6	0.2000 (3)	−0.0220 (3)	−0.0017 (3)	0.0268 (5)
H6	0.1909	0.0374	−0.0485	0.032*
C7	0.0709 (3)	−0.1345 (3)	−0.0177 (3)	0.0288 (5)
H7	−0.0269	−0.1528	−0.0757	0.035*
C8	0.0835 (3)	−0.2206 (3)	0.0503 (3)	0.0258 (5)
C9	0.2258 (3)	−0.1966 (3)	0.1332 (3)	0.0265 (5)
H9	0.2337	−0.2575	0.1785	0.032*
C10	0.3569 (3)	−0.0831 (3)	0.1496 (2)	0.0259 (5)
H10	0.4546	−0.0663	0.2061	0.031*
C11	0.5936 (3)	0.6910 (3)	0.1494 (3)	0.0303 (6)
C12	0.7100 (3)	0.6922 (3)	0.2648 (3)	0.0285 (5)
H12	0.8114	0.7645	0.2938	0.034*
C13	0.6992 (3)	0.6111 (3)	0.3355 (3)	0.0267 (5)
H13	0.7924	0.6353	0.4071	0.032*
C14	0.5606 (3)	0.4884 (3)	0.3167 (3)	0.0264 (5)
C15	0.4783 (3)	0.3083 (3)	0.4117 (2)	0.0242 (5)
C16	0.3212 (3)	0.2463 (3)	0.3389 (3)	0.0275 (5)
H16	0.2801	0.2840	0.2798	0.033*
C17	0.2245 (3)	0.1295 (3)	0.3523 (3)	0.0301 (6)
H17	0.1172	0.0864	0.3021	0.036*
C18	0.2856 (3)	0.0760 (3)	0.4393 (3)	0.0283 (5)
C19	0.4411 (3)	0.1383 (3)	0.5140 (3)	0.0295 (6)
H19	0.4816	0.1018	0.5747	0.035*
C20	0.5381 (3)	0.2542 (3)	0.5001 (3)	0.0281 (5)
H20	0.6454	0.2970	0.5507	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02180 (15)	0.04107 (17)	0.04829 (18)	0.00807 (12)	0.01290 (12)	0.02689 (14)
Br2	0.03275 (17)	0.05026 (19)	0.04698 (19)	0.01005 (14)	0.01376 (14)	0.03313 (15)
O1	0.0210 (10)	0.0495 (12)	0.0552 (13)	0.0046 (9)	−0.0007 (9)	0.0337 (11)
O2	0.0201 (9)	0.0506 (12)	0.0461 (12)	0.0086 (9)	0.0043 (9)	0.0346 (10)
O3	0.0198 (9)	0.0430 (11)	0.0416 (11)	0.0110 (8)	0.0067 (8)	0.0294 (9)
O4	0.0343 (11)	0.0431 (11)	0.0466 (12)	0.0149 (9)	0.0102 (9)	0.0328 (10)
O5	0.0256 (10)	0.0498 (12)	0.0474 (12)	0.0107 (9)	0.0044 (9)	0.0351 (10)
O6	0.0239 (10)	0.0479 (11)	0.0427 (11)	0.0076 (9)	0.0016 (9)	0.0318 (10)
N1	0.0205 (10)	0.0247 (10)	0.0228 (10)	0.0105 (8)	0.0067 (8)	0.0137 (9)
N2	0.0196 (10)	0.0255 (11)	0.0235 (11)	0.0095 (9)	0.0031 (9)	0.0100 (9)
C1	0.0214 (13)	0.0349 (14)	0.0299 (13)	0.0102 (11)	0.0075 (11)	0.0164 (12)
C2	0.0226 (13)	0.0275 (13)	0.0301 (13)	0.0094 (10)	0.0088 (11)	0.0164 (11)
C3	0.0205 (12)	0.0255 (12)	0.0240 (12)	0.0104 (10)	0.0077 (10)	0.0112 (10)
C4	0.0199 (12)	0.0259 (12)	0.0217 (12)	0.0124 (10)	0.0074 (10)	0.0107 (10)
C5	0.0191 (11)	0.0235 (12)	0.0227 (12)	0.0109 (9)	0.0082 (10)	0.0097 (10)
C6	0.0240 (13)	0.0283 (13)	0.0268 (13)	0.0134 (11)	0.0076 (10)	0.0132 (11)
C7	0.0198 (12)	0.0325 (14)	0.0301 (13)	0.0118 (11)	0.0077 (11)	0.0132 (11)
C8	0.0224 (12)	0.0261 (12)	0.0265 (13)	0.0084 (10)	0.0114 (10)	0.0123 (11)
C9	0.0235 (12)	0.0315 (13)	0.0270 (13)	0.0129 (11)	0.0106 (10)	0.0169 (11)
C10	0.0203 (12)	0.0314 (13)	0.0249 (12)	0.0121 (10)	0.0070 (10)	0.0145 (11)
C11	0.0279 (14)	0.0324 (14)	0.0326 (14)	0.0163 (11)	0.0103 (11)	0.0179 (12)
C12	0.0227 (13)	0.0256 (12)	0.0298 (13)	0.0095 (10)	0.0056 (11)	0.0118 (11)
C13	0.0227 (12)	0.0265 (13)	0.0243 (12)	0.0119 (10)	0.0039 (10)	0.0095 (10)
C14	0.0258 (13)	0.0288 (13)	0.0231 (12)	0.0148 (10)	0.0061 (10)	0.0123 (10)
C15	0.0239 (13)	0.0252 (12)	0.0205 (12)	0.0124 (10)	0.0073 (10)	0.0081 (10)
C16	0.0237 (13)	0.0318 (13)	0.0231 (12)	0.0133 (11)	0.0059 (10)	0.0121 (11)
C17	0.0225 (13)	0.0366 (14)	0.0262 (13)	0.0121 (11)	0.0077 (11)	0.0137 (11)
C18	0.0288 (13)	0.0260 (13)	0.0262 (13)	0.0096 (11)	0.0120 (11)	0.0114 (11)
C19	0.0290 (14)	0.0341 (14)	0.0279 (13)	0.0168 (11)	0.0098 (11)	0.0176 (11)
C20	0.0239 (13)	0.0311 (13)	0.0256 (12)	0.0137 (11)	0.0052 (10)	0.0132 (11)

Geometric parameters (Å, º)

Br1—C8	1.892 (2)	C6—C7	1.376 (3)
Br2—C18	1.893 (3)	C6—H6	0.9500
O1—C1	1.218 (3)	C7—C8	1.378 (3)
O2—C1	1.305 (3)	C7—H7	0.9500
O2—H2O	0.94 (4)	C8—C9	1.388 (3)
O3—C4	1.243 (3)	C9—C10	1.393 (3)
O4—C11	1.216 (3)	C9—H9	0.9500
O5—C11	1.308 (3)	C10—H10	0.9500
O5—H5O	0.85 (4)	C11—C12	1.487 (4)
O6—C14	1.244 (3)	C12—C13	1.336 (3)
N1—C4	1.342 (3)	C12—H12	0.9500
N1—C5	1.415 (3)	C13—C14	1.480 (3)
N1—H1N	0.88 (3)	C13—H13	0.9500
N2—C14	1.337 (3)	C15—C16	1.389 (3)
N2—C15	1.421 (3)	C15—C20	1.394 (3)
N2—H2N	0.80 (3)	C16—C17	1.387 (4)
C1—C2	1.483 (4)	C16—H16	0.9500
C2—C3	1.338 (3)	C17—C18	1.384 (4)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.483 (3)	C18—C19	1.379 (4)
C3—H3	0.9500	C19—C20	1.385 (4)
C5—C10	1.394 (3)	C19—H19	0.9500
C5—C6	1.396 (3)	C20—H20	0.9500
C1—O2—H2O	112 (2)	C10—C9—H9	120.1
C11—O5—H5O	114 (3)	C9—C10—C5	119.8 (2)
C4—N1—C5	128.5 (2)	C9—C10—H10	120.1
C4—N1—H1N	119.0 (18)	C5—C10—H10	120.1
C5—N1—H1N	112.1 (18)	O4—C11—O5	120.6 (2)
C14—N2—C15	128.7 (2)	O4—C11—C12	118.5 (2)
C14—N2—H2N	118 (2)	O5—C11—C12	120.9 (2)
C15—N2—H2N	113 (2)	C13—C12—C11	132.3 (2)
O1—C1—O2	120.5 (2)	C13—C12—H12	113.9
O1—C1—C2	118.4 (2)	C11—C12—H12	113.9
O2—C1—C2	121.2 (2)	C12—C13—C14	128.3 (2)
C3—C2—C1	132.4 (2)	C12—C13—H13	115.8
C3—C2—H2	113.8	C14—C13—H13	115.8
C1—C2—H2	113.8	O6—C14—N2	122.0 (2)
C2—C3—C4	128.0 (2)	O6—C14—C13	123.3 (2)
C2—C3—H3	116.0	N2—C14—C13	114.8 (2)
C4—C3—H3	116.0	C16—C15—C20	119.8 (2)
O3—C4—N1	122.5 (2)	C16—C15—N2	123.8 (2)
O3—C4—C3	123.4 (2)	C20—C15—N2	116.4 (2)
N1—C4—C3	114.1 (2)	C17—C16—C15	120.1 (2)
C10—C5—C6	119.4 (2)	C17—C16—H16	120.0
C10—C5—N1	123.9 (2)	C15—C16—H16	120.0
C6—C5—N1	116.7 (2)	C18—C17—C16	119.5 (2)
C7—C6—C5	120.5 (2)	C18—C17—H17	120.2
C7—C6—H6	119.7	C16—C17—H17	120.2
C5—C6—H6	119.7	C19—C18—C17	120.9 (2)
C6—C7—C8	120.0 (2)	C19—C18—Br2	119.21 (19)
C6—C7—H7	120.0	C17—C18—Br2	119.9 (2)
C8—C7—H7	120.0	C18—C19—C20	119.7 (2)
C7—C8—C9	120.5 (2)	C18—C19—H19	120.1
C7—C8—Br1	119.41 (19)	C20—C19—H19	120.1
C9—C8—Br1	120.04 (18)	C19—C20—C15	120.0 (2)
C8—C9—C10	119.7 (2)	C19—C20—H20	120.0
C8—C9—H9	120.1	C15—C20—H20	120.0
O1—C1—C2—C3	−177.8 (3)	O4—C11—C12—C13	−180.0 (3)
O2—C1—C2—C3	3.1 (4)	O5—C11—C12—C13	0.4 (4)
C1—C2—C3—C4	0.5 (4)	C11—C12—C13—C14	1.1 (4)
C5—N1—C4—O3	1.3 (4)	C15—N2—C14—O6	−0.6 (4)
C5—N1—C4—C3	−178.1 (2)	C15—N2—C14—C13	−179.6 (2)
C2—C3—C4—O3	−0.7 (4)	C12—C13—C14—O6	0.9 (4)
C2—C3—C4—N1	178.6 (2)	C12—C13—C14—N2	179.8 (2)
C4—N1—C5—C10	−6.2 (4)	C14—N2—C15—C16	−8.9 (4)
C4—N1—C5—C6	173.9 (2)	C14—N2—C15—C20	171.7 (2)
C10—C5—C6—C7	0.9 (3)	C20—C15—C16—C17	−1.1 (4)
N1—C5—C6—C7	−179.2 (2)	N2—C15—C16—C17	179.6 (2)
C5—C6—C7—C8	0.2 (4)	C15—C16—C17—C18	0.5 (4)
C6—C7—C8—C9	−1.2 (4)	C16—C17—C18—C19	0.7 (4)
C6—C7—C8—Br1	179.52 (18)	C16—C17—C18—Br2	−179.77 (18)
C7—C8—C9—C10	1.1 (4)	C17—C18—C19—C20	−1.2 (4)
Br1—C8—C9—C10	−179.66 (18)	Br2—C18—C19—C20	179.28 (19)
C8—C9—C10—C5	0.0 (4)	C18—C19—C20—C15	0.5 (4)
C6—C5—C10—C9	−1.0 (3)	C16—C15—C20—C19	0.6 (4)
N1—C5—C10—C9	179.1 (2)	N2—C15—C20—C19	180.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3	0.94 (4)	1.56 (4)	2.487 (3)	171 (3)
O5—H5O···O6	0.85 (4)	1.65 (4)	2.484 (3)	166 (4)
N1—H1N···O4^i	0.88 (3)	1.95 (3)	2.817 (3)	173 (2)
N2—H2N···O1^ii	0.80 (3)	2.02 (3)	2.813 (3)	173 (3)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1.