organic compounds
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—HO hydrogen bonds [NO = 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—HO hydrogen bonds [both OO = 2.486 (2) Å]. There are two molecules in the asymmetric unit.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026030/fl6126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026030/fl6126Isup2.hkl |
CCDC reference: 255923
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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.
3-[(2,4,6-Trichloroanilino)carbonyl]prop-2-enoic acid top
Crystal data top
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) Å3 |
Data collection top
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 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.16P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
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···O4i | 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···O1ii | 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. |