organic compounds
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—HO hydrogen bonds [NO = 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—HO hydrogen bonds [OO = 2.484 (3) and 2.487 (3) Å]. There are two molecules in the asymmetric unit.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026029/fl6125sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026029/fl6125Isup2.hkl |
CCDC reference: 255922
Computing details top
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 top
Crystal data top
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) Å3 |
Data collection top
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 top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.5P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
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···O4i | 0.88 (3) | 1.95 (3) | 2.817 (3) | 173 (2) |
N2—H2N···O1ii | 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. |