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The title molecule, C
10H
8ClNO
3, 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.
Supporting information
CCDC reference: 200784
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.25 × 0.23 × 0.10 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.102P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.006 (2) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···O1i | 3.121 (3) | C4···O2iii | 3.576 (3) |
Cl···O3i | 3.458 (3) | C6···C8iv | 3.588 (4) |
C2···C8ii | 3.494 (5) | C7···O3v | 3.538 (4) |
C3···C8ii | 3.454 (5) | O3···O3v | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2iii | 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···O2iii | 0.93 | 2.58 | 3.315 (3) | 137 |
C8—H8···O1iii | 0.93 | 2.65 | 3.567 (4) | 168 |
C9—H9···Clvi | 0.93 | 2.86 | 3.720 (3) | 154 |
Symmetry codes: (iii) x, −y+3/2, z−1/2; (vi) x, y+1, z. |
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