There are two molecules, C
15H
14N
2O
3, in the asymmetric unit of the title compound, the first structurally characterized carbamoyl benzaldehyde oxime derivative; these molecules do not differ significantly. Intermolecular N-H
O hydrogen bonds connect molecules into infinite ...
ABAB... ribbons along the [100] direction.
Supporting information
CCDC reference: 278556
The method of synthesis of (1) will be described elsewhere (Mohamed, 2004). The crystals for data collection were grown from a methanol solution by slow evaporation. Please consider providing full details of the synthesis here, or a more accessible reference; since the existing reference is to a personal communication, readers have no way of obtaining further information.
C—H distances are in the range 0.90 (2)–1.08 (3) Å.
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: program (reference?); software used to prepare material for publication: program (reference?).
(
E)-4-Methoxybenzaldehyde
O-(
N-phenylcarbamoyl)oxime
top
Crystal data top
C15H14N2O3 | Z = 4 |
Mr = 270.28 | F(000) = 568 |
Triclinic, P1 | Dx = 1.364 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8037 (8) Å | Cell parameters from 3412 reflections |
b = 12.1484 (15) Å | θ = 4–20° |
c = 12.9823 (17) Å | µ = 0.10 mm−1 |
α = 75.275 (11)° | T = 100 K |
β = 81.075 (9)° | Plate, colourless |
γ = 80.746 (9)° | 0.3 × 0.2 × 0.05 mm |
V = 1315.9 (3) Å3 | |
Data collection top
Kuma KM-4-CCD four-circle diffractometer | 2749 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 26.0°, θmin = 2.7° |
ω scans | h = −10→10 |
10887 measured reflections | k = −14→14 |
5124 independent reflections | l = −11→16 |
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)] = 0.053 | All H-atom parameters refined |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0517P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max = 0.001 |
5124 reflections | Δρmax = 0.25 e Å−3 |
456 parameters | Δρmin = −0.28 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: 0.0032 (9) |
Crystal data top
C15H14N2O3 | γ = 80.746 (9)° |
Mr = 270.28 | V = 1315.9 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.8037 (8) Å | Mo Kα radiation |
b = 12.1484 (15) Å | µ = 0.10 mm−1 |
c = 12.9823 (17) Å | T = 100 K |
α = 75.275 (11)° | 0.3 × 0.2 × 0.05 mm |
β = 81.075 (9)° | |
Data collection top
Kuma KM-4-CCD four-circle diffractometer | 2749 reflections with I > 2σ(I) |
10887 measured reflections | Rint = 0.056 |
5124 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.128 | All H-atom parameters refined |
S = 0.94 | Δρmax = 0.25 e Å−3 |
5124 reflections | Δρmin = −0.28 e Å−3 |
456 parameters | |
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 | |
N1A | 0.3315 (3) | 0.68748 (19) | 0.25544 (19) | 0.0257 (6) | |
H1A | 0.407 (4) | 0.701 (2) | 0.281 (2) | 0.045 (10)* | |
C11A | 0.3110 (3) | 0.5702 (2) | 0.2750 (2) | 0.0223 (6) | |
C12A | 0.2497 (3) | 0.5258 (2) | 0.2039 (2) | 0.0271 (7) | |
H12A | 0.213 (3) | 0.578 (2) | 0.1387 (19) | 0.023 (3)* | |
C13A | 0.2420 (3) | 0.4090 (3) | 0.2248 (2) | 0.0301 (7) | |
H13A | 0.198 (3) | 0.385 (2) | 0.178 (2) | 0.023 (3)* | |
C14A | 0.2962 (3) | 0.3350 (2) | 0.3158 (2) | 0.0278 (7) | |
H14A | 0.293 (3) | 0.251 (2) | 0.3247 (19) | 0.023 (3)* | |
C15A | 0.3560 (3) | 0.3801 (2) | 0.3875 (2) | 0.0273 (7) | |
H15A | 0.391 (3) | 0.325 (2) | 0.4564 (19) | 0.023 (3)* | |
C16A | 0.3641 (3) | 0.4964 (2) | 0.3667 (2) | 0.0256 (7) | |
H16A | 0.405 (3) | 0.525 (2) | 0.414 (2) | 0.023 (3)* | |
C1A | 0.2569 (3) | 0.7766 (2) | 0.1897 (2) | 0.0245 (6) | |
O11A | 0.1446 (2) | 0.77723 (15) | 0.14535 (15) | 0.0290 (5) | |
O12A | 0.33374 (19) | 0.86974 (14) | 0.17702 (14) | 0.0265 (5) | |
N2A | 0.2533 (2) | 0.97497 (18) | 0.11963 (17) | 0.0256 (6) | |
C2A | 0.3492 (3) | 1.0488 (2) | 0.0901 (2) | 0.0246 (7) | |
H2A | 0.454 (3) | 1.028 (2) | 0.101 (2) | 0.031 (8)* | |
C21A | 0.2984 (3) | 1.1670 (2) | 0.0365 (2) | 0.0232 (6) | |
C22A | 0.1409 (3) | 1.2086 (2) | 0.0270 (2) | 0.0261 (7) | |
H22A | 0.062 (3) | 1.157 (2) | 0.052 (2) | 0.038 (4)* | |
C23A | 0.0975 (3) | 1.3214 (2) | −0.0213 (2) | 0.0257 (7) | |
H23A | −0.015 (3) | 1.351 (2) | −0.030 (2) | 0.038 (4)* | |
C24A | 0.2081 (3) | 1.3962 (2) | −0.0629 (2) | 0.0259 (7) | |
O24A | 0.1503 (2) | 1.50711 (15) | −0.10869 (15) | 0.0346 (5) | |
C241 | 0.2591 (4) | 1.5878 (3) | −0.1531 (3) | 0.0385 (8) | |
H24A | 0.313 (4) | 1.598 (2) | −0.100 (2) | 0.053 (5)* | |
H24B | 0.196 (3) | 1.666 (3) | −0.191 (2) | 0.053 (5)* | |
H24C | 0.335 (4) | 1.561 (2) | −0.212 (2) | 0.053 (5)* | |
C25A | 0.3636 (3) | 1.3579 (2) | −0.0555 (2) | 0.0287 (7) | |
H25A | 0.436 (3) | 1.411 (2) | −0.084 (2) | 0.038 (4)* | |
C26A | 0.4066 (3) | 1.2438 (2) | −0.0053 (2) | 0.0276 (7) | |
H26A | 0.514 (3) | 1.214 (2) | −0.001 (2) | 0.038 (4)* | |
N1B | 0.8131 (3) | 0.79083 (18) | 0.24317 (18) | 0.0249 (6) | |
H1B | 0.905 (3) | 0.787 (2) | 0.214 (2) | 0.043 (9)* | |
C11B | 0.7436 (3) | 0.9059 (2) | 0.2334 (2) | 0.0229 (6) | |
C12B | 0.6232 (3) | 0.9367 (2) | 0.3087 (2) | 0.0267 (7) | |
H12B | 0.578 (3) | 0.871 (2) | 0.374 (2) | 0.031 (3)* | |
C13B | 0.5661 (3) | 1.0526 (2) | 0.2992 (2) | 0.0306 (7) | |
H13B | 0.472 (3) | 1.074 (2) | 0.3566 (19) | 0.031 (3)* | |
C14B | 0.6267 (3) | 1.1366 (3) | 0.2166 (2) | 0.0303 (7) | |
H14B | 0.584 (3) | 1.219 (2) | 0.2135 (19) | 0.031 (3)* | |
C15B | 0.7458 (3) | 1.1054 (2) | 0.1416 (2) | 0.0292 (7) | |
H15B | 0.790 (3) | 1.166 (2) | 0.080 (2) | 0.031 (3)* | |
C16B | 0.8041 (3) | 0.9906 (2) | 0.1508 (2) | 0.0261 (7) | |
H16B | 0.885 (3) | 0.969 (2) | 0.098 (2) | 0.031 (3)* | |
C1B | 0.7492 (3) | 0.6972 (2) | 0.3018 (2) | 0.0250 (6) | |
O11B | 0.6162 (2) | 0.69222 (15) | 0.34259 (14) | 0.0288 (5) | |
O12B | 0.8630 (2) | 0.60519 (15) | 0.31233 (14) | 0.0286 (5) | |
N2B | 0.8010 (3) | 0.49871 (18) | 0.36344 (18) | 0.0276 (6) | |
C2B | 0.9089 (3) | 0.4296 (2) | 0.4098 (2) | 0.0250 (7) | |
H2B | 1.006 (3) | 0.453 (2) | 0.4117 (19) | 0.024 (7)* | |
C21B | 0.8831 (3) | 0.3119 (2) | 0.4659 (2) | 0.0237 (6) | |
C22B | 0.7512 (3) | 0.2643 (2) | 0.4603 (2) | 0.0261 (7) | |
H22B | 0.672 (3) | 0.316 (2) | 0.411 (2) | 0.040 (4)* | |
C23B | 0.7329 (3) | 0.1532 (2) | 0.5145 (2) | 0.0276 (7) | |
H23B | 0.641 (3) | 0.117 (2) | 0.515 (2) | 0.040 (4)* | |
C24B | 0.8456 (3) | 0.0862 (2) | 0.5762 (2) | 0.0226 (6) | |
O24B | 0.8181 (2) | −0.02352 (15) | 0.62655 (14) | 0.0290 (5) | |
C242 | 0.9342 (3) | −0.0943 (3) | 0.6893 (2) | 0.0275 (7) | |
H24D | 1.032 (3) | −0.108 (2) | 0.637 (2) | 0.034 (4)* | |
H24E | 0.893 (3) | −0.175 (2) | 0.722 (2) | 0.034 (4)* | |
H24F | 0.950 (3) | −0.061 (2) | 0.750 (2) | 0.034 (4)* | |
C25B | 0.9780 (3) | 0.1313 (2) | 0.5829 (2) | 0.0256 (7) | |
H25B | 1.062 (3) | 0.080 (2) | 0.623 (2) | 0.040 (4)* | |
C26B | 0.9961 (3) | 0.2436 (2) | 0.5276 (2) | 0.0266 (7) | |
H26B | 1.088 (3) | 0.278 (2) | 0.532 (2) | 0.040 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0194 (13) | 0.0265 (14) | 0.0308 (15) | −0.0045 (11) | −0.0092 (11) | −0.0014 (11) |
C11A | 0.0144 (14) | 0.0215 (15) | 0.0292 (16) | −0.0023 (11) | −0.0003 (12) | −0.0040 (12) |
C12A | 0.0247 (16) | 0.0288 (17) | 0.0251 (16) | −0.0010 (12) | −0.0059 (13) | −0.0014 (13) |
C13A | 0.0288 (17) | 0.0353 (18) | 0.0302 (18) | −0.0058 (13) | −0.0067 (14) | −0.0122 (15) |
C14A | 0.0210 (15) | 0.0228 (16) | 0.0359 (18) | −0.0017 (12) | −0.0002 (13) | −0.0029 (14) |
C15A | 0.0187 (15) | 0.0256 (16) | 0.0315 (17) | 0.0011 (12) | −0.0012 (13) | 0.0007 (13) |
C16A | 0.0195 (15) | 0.0321 (17) | 0.0236 (16) | −0.0015 (12) | −0.0044 (12) | −0.0039 (13) |
C1A | 0.0204 (15) | 0.0242 (16) | 0.0263 (16) | −0.0039 (12) | −0.0006 (13) | −0.0019 (13) |
O11A | 0.0191 (10) | 0.0302 (11) | 0.0354 (12) | −0.0020 (8) | −0.0070 (9) | −0.0022 (9) |
O12A | 0.0223 (10) | 0.0202 (10) | 0.0350 (12) | −0.0010 (8) | −0.0081 (9) | −0.0012 (8) |
N2A | 0.0230 (13) | 0.0211 (13) | 0.0283 (14) | 0.0036 (10) | −0.0055 (10) | −0.0003 (10) |
C2A | 0.0231 (16) | 0.0293 (17) | 0.0198 (15) | −0.0036 (13) | −0.0002 (13) | −0.0042 (13) |
C21A | 0.0245 (15) | 0.0242 (15) | 0.0205 (15) | −0.0029 (12) | −0.0017 (12) | −0.0054 (12) |
C22A | 0.0245 (16) | 0.0282 (17) | 0.0239 (16) | −0.0041 (12) | −0.0035 (12) | −0.0024 (13) |
C23A | 0.0231 (16) | 0.0281 (16) | 0.0264 (16) | −0.0033 (12) | −0.0040 (13) | −0.0067 (13) |
C24A | 0.0338 (17) | 0.0227 (15) | 0.0214 (16) | −0.0056 (13) | −0.0038 (13) | −0.0038 (12) |
O24A | 0.0356 (12) | 0.0250 (11) | 0.0400 (13) | −0.0038 (9) | −0.0032 (10) | −0.0023 (9) |
C241 | 0.052 (2) | 0.0269 (18) | 0.036 (2) | −0.0169 (16) | −0.0063 (17) | 0.0014 (15) |
C25A | 0.0285 (17) | 0.0300 (17) | 0.0279 (17) | −0.0093 (13) | 0.0002 (13) | −0.0059 (14) |
C26A | 0.0198 (15) | 0.0322 (17) | 0.0294 (17) | −0.0024 (13) | 0.0009 (13) | −0.0074 (13) |
N1B | 0.0197 (13) | 0.0222 (13) | 0.0309 (14) | −0.0048 (10) | 0.0001 (11) | −0.0035 (11) |
C11B | 0.0177 (14) | 0.0207 (15) | 0.0278 (16) | −0.0001 (11) | −0.0056 (12) | −0.0012 (12) |
C12B | 0.0212 (15) | 0.0246 (16) | 0.0312 (17) | −0.0023 (12) | −0.0020 (13) | −0.0020 (13) |
C13B | 0.0204 (15) | 0.0334 (18) | 0.0375 (18) | −0.0009 (13) | −0.0002 (13) | −0.0111 (14) |
C14B | 0.0219 (15) | 0.0299 (17) | 0.0392 (19) | −0.0026 (13) | −0.0038 (14) | −0.0085 (14) |
C15B | 0.0212 (15) | 0.0271 (17) | 0.0387 (19) | −0.0060 (12) | −0.0056 (13) | −0.0036 (14) |
C16B | 0.0189 (15) | 0.0299 (17) | 0.0295 (17) | −0.0032 (12) | −0.0037 (13) | −0.0064 (13) |
C1B | 0.0226 (16) | 0.0268 (16) | 0.0260 (16) | −0.0012 (12) | −0.0080 (13) | −0.0050 (13) |
O11B | 0.0193 (10) | 0.0304 (11) | 0.0339 (12) | −0.0040 (8) | −0.0025 (9) | −0.0025 (9) |
O12B | 0.0209 (10) | 0.0242 (11) | 0.0375 (12) | −0.0017 (8) | −0.0011 (9) | −0.0038 (9) |
N2B | 0.0248 (13) | 0.0214 (13) | 0.0331 (14) | −0.0048 (10) | −0.0007 (11) | −0.0008 (11) |
C2B | 0.0223 (16) | 0.0258 (16) | 0.0255 (16) | −0.0015 (13) | −0.0002 (13) | −0.0064 (13) |
C21B | 0.0188 (14) | 0.0273 (16) | 0.0230 (15) | 0.0003 (12) | −0.0007 (12) | −0.0057 (12) |
C22B | 0.0157 (14) | 0.0324 (17) | 0.0265 (16) | −0.0013 (12) | 0.0006 (12) | −0.0036 (13) |
C23B | 0.0153 (15) | 0.0329 (17) | 0.0321 (17) | −0.0028 (12) | −0.0013 (13) | −0.0043 (14) |
C24B | 0.0196 (15) | 0.0250 (16) | 0.0225 (15) | −0.0033 (12) | 0.0005 (12) | −0.0057 (12) |
O24B | 0.0241 (11) | 0.0266 (11) | 0.0332 (11) | −0.0041 (8) | −0.0051 (9) | 0.0001 (9) |
C242 | 0.0265 (16) | 0.0269 (17) | 0.0255 (17) | −0.0013 (13) | −0.0021 (13) | −0.0013 (14) |
C25B | 0.0214 (15) | 0.0301 (17) | 0.0260 (16) | −0.0012 (12) | −0.0080 (12) | −0.0063 (13) |
C26B | 0.0237 (16) | 0.0300 (17) | 0.0270 (16) | −0.0057 (13) | −0.0047 (13) | −0.0061 (13) |
Geometric parameters (Å, º) top
N1A—C1A | 1.345 (3) | N1B—C1B | 1.350 (3) |
N1A—C11A | 1.419 (3) | N1B—C11B | 1.415 (3) |
N1A—H1A | 0.84 (3) | N1B—H1B | 0.84 (3) |
C11A—C16A | 1.391 (4) | C11B—C16B | 1.389 (4) |
C11A—C12A | 1.391 (4) | C11B—C12B | 1.399 (4) |
C12A—C13A | 1.386 (4) | C12B—C13B | 1.398 (4) |
C12A—H12A | 0.99 (2) | C12B—H12B | 1.08 (3) |
C13A—C14A | 1.389 (4) | C13B—C14B | 1.384 (4) |
C13A—H13A | 0.90 (2) | C13B—H13B | 1.07 (2) |
C14A—C15A | 1.395 (4) | C14B—C15B | 1.391 (4) |
C14A—H14A | 1.00 (2) | C14B—H14B | 1.00 (3) |
C15A—C16A | 1.381 (4) | C15B—C16B | 1.389 (4) |
C15A—H15A | 1.03 (2) | C15B—H15B | 1.02 (3) |
C16A—H16A | 0.92 (2) | C16B—H16B | 0.97 (2) |
C1A—O11A | 1.217 (3) | C1B—O11B | 1.212 (3) |
C1A—O12A | 1.371 (3) | C1B—O12B | 1.369 (3) |
O12A—N2A | 1.442 (3) | O12B—N2B | 1.445 (3) |
N2A—C2A | 1.277 (3) | N2B—C2B | 1.278 (3) |
C2A—C21A | 1.459 (4) | C2B—C21B | 1.466 (4) |
C2A—H2A | 0.94 (3) | C2B—H2B | 0.95 (3) |
C21A—C26A | 1.393 (4) | C21B—C22B | 1.397 (4) |
C21A—C22A | 1.411 (4) | C21B—C26B | 1.401 (4) |
C22A—C23A | 1.373 (4) | C22B—C23B | 1.376 (4) |
C22A—H22A | 0.97 (3) | C22B—H22B | 1.04 (3) |
C23A—C24A | 1.392 (4) | C23B—C24B | 1.393 (4) |
C23A—H23A | 1.01 (3) | C23B—H23B | 0.98 (3) |
C24A—O24A | 1.376 (3) | C24B—O24B | 1.370 (3) |
C24A—C25A | 1.383 (4) | C24B—C25B | 1.388 (4) |
O24A—C241 | 1.433 (3) | O24B—C242 | 1.439 (3) |
C241—H24A | 0.94 (3) | C242—H24D | 1.03 (3) |
C241—H24B | 1.06 (3) | C242—H24E | 1.06 (3) |
C241—H24C | 1.02 (3) | C242—H24F | 1.00 (3) |
C25A—C26A | 1.392 (4) | C25B—C26B | 1.393 (4) |
C25A—H25A | 0.95 (3) | C25B—H25B | 1.01 (3) |
C26A—H26A | 0.96 (3) | C26B—H26B | 0.99 (3) |
| | | |
C1A—N1A—C11A | 126.9 (3) | C1B—N1B—C11B | 125.6 (2) |
C1A—N1A—H1A | 117 (2) | C1B—N1B—H1B | 123 (2) |
C11A—N1A—H1A | 116 (2) | C11B—N1B—H1B | 111 (2) |
C16A—C11A—C12A | 119.4 (3) | C16B—C11B—C12B | 119.6 (3) |
C16A—C11A—N1A | 117.5 (3) | C16B—C11B—N1B | 118.7 (2) |
C12A—C11A—N1A | 123.0 (2) | C12B—C11B—N1B | 121.6 (2) |
C13A—C12A—C11A | 120.0 (3) | C13B—C12B—C11B | 119.1 (3) |
C13A—C12A—H12A | 121 (1) | C13B—C12B—H12B | 121 (1) |
C11A—C12A—H12A | 119 (1) | C11B—C12B—H12B | 120 (1) |
C12A—C13A—C14A | 120.7 (3) | C14B—C13B—C12B | 121.0 (3) |
C12A—C13A—H13A | 117 (2) | C14B—C13B—H13B | 121 (1) |
C14A—C13A—H13A | 123 (2) | C12B—C13B—H13B | 118 (1) |
C13A—C14A—C15A | 119.1 (3) | C13B—C14B—C15B | 119.6 (3) |
C13A—C14A—H14A | 117 (1) | C13B—C14B—H14B | 119 (2) |
C15A—C14A—H14A | 124 (1) | C15B—C14B—H14B | 122 (2) |
C16A—C15A—C14A | 120.2 (3) | C16B—C15B—C14B | 119.8 (3) |
C16A—C15A—H15A | 121 (1) | C16B—C15B—H15B | 119 (1) |
C14A—C15A—H15A | 118 (1) | C14B—C15B—H15B | 121 (1) |
C15A—C16A—C11A | 120.6 (3) | C15B—C16B—C11B | 120.9 (3) |
C15A—C16A—H16A | 119 (2) | C15B—C16B—H16B | 120 (2) |
C11A—C16A—H16A | 120 (2) | C11B—C16B—H16B | 119 (2) |
O11A—C1A—N1A | 127.9 (3) | O11B—C1B—N1B | 127.7 (3) |
O11A—C1A—O12A | 124.5 (2) | O11B—C1B—O12B | 124.0 (2) |
N1A—C1A—O12A | 107.6 (2) | N1B—C1B—O12B | 108.3 (2) |
C1A—O12A—N2A | 113.0 (2) | C1B—O12B—N2B | 111.9 (2) |
C2A—N2A—O12A | 107.6 (2) | C2B—N2B—O12B | 107.3 (2) |
N2A—C2A—C21A | 120.5 (3) | N2B—C2B—C21B | 120.4 (3) |
N2A—C2A—H2A | 121 (2) | N2B—C2B—H2B | 122 (2) |
C21A—C2A—H2A | 119 (2) | C21B—C2B—H2B | 118 (2) |
C26A—C21A—C22A | 117.7 (3) | C22B—C21B—C26B | 118.3 (3) |
C26A—C21A—C2A | 120.0 (3) | C22B—C21B—C2B | 123.0 (2) |
C22A—C21A—C2A | 122.3 (2) | C26B—C21B—C2B | 118.6 (2) |
C23A—C22A—C21A | 120.5 (3) | C23B—C22B—C21B | 120.7 (3) |
C23A—C22A—H22A | 119 (2) | C23B—C22B—H22B | 123 (2) |
C21A—C22A—H22A | 120 (2) | C21B—C22B—H22B | 117 (2) |
C22A—C23A—C24A | 120.7 (3) | C22B—C23B—C24B | 120.5 (3) |
C22A—C23A—H23A | 121 (2) | C22B—C23B—H23B | 124 (2) |
C24A—C23A—H23A | 119 (2) | C24B—C23B—H23B | 116 (2) |
O24A—C24A—C25A | 124.4 (2) | O24B—C24B—C25B | 123.5 (2) |
O24A—C24A—C23A | 115.3 (2) | O24B—C24B—C23B | 116.5 (2) |
C25A—C24A—C23A | 120.3 (3) | C25B—C24B—C23B | 120.0 (3) |
C24A—O24A—C241 | 117.6 (2) | C24B—O24B—C242 | 117.2 (2) |
O24A—C241—H24A | 111 (2) | O24B—C242—H24D | 107 (1) |
O24A—C241—H24B | 108 (2) | O24B—C242—H24E | 106 (1) |
H24A—C241—H24B | 112 (2) | H24D—C242—H24E | 108 (2) |
O24A—C241—H24C | 110 (2) | O24B—C242—H24F | 112 (2) |
H24A—C241—H24C | 110 (3) | H24D—C242—H24F | 115 (2) |
H24B—C241—H24C | 106 (2) | H24E—C242—H24F | 109 (2) |
C24A—C25A—C26A | 118.7 (3) | C24B—C25B—C26B | 119.2 (3) |
C24A—C25A—H25A | 119 (2) | C24B—C25B—H25B | 119 (2) |
C26A—C25A—H25A | 123 (2) | C26B—C25B—H25B | 122 (2) |
C25A—C26A—C21A | 122.2 (3) | C25B—C26B—C21B | 121.3 (3) |
C25A—C26A—H26A | 121 (2) | C25B—C26B—H26B | 121 (2) |
C21A—C26A—H26A | 117 (2) | C21B—C26B—H26B | 118 (2) |
| | | |
C1A—N1A—C11A—C16A | −161.8 (2) | C1B—N1B—C11B—C16B | −164.2 (3) |
C1A—N1A—C11A—C12A | 22.2 (4) | C1B—N1B—C11B—C12B | 20.2 (4) |
C16A—C11A—C12A—C13A | 0.0 (4) | C16B—C11B—C12B—C13B | 0.1 (4) |
N1A—C11A—C12A—C13A | 175.9 (2) | N1B—C11B—C12B—C13B | 175.6 (2) |
C11A—C12A—C13A—C14A | −0.5 (4) | C11B—C12B—C13B—C14B | 0.1 (4) |
C12A—C13A—C14A—C15A | 1.2 (4) | C12B—C13B—C14B—C15B | 0.2 (4) |
C13A—C14A—C15A—C16A | −1.4 (4) | C13B—C14B—C15B—C16B | −0.7 (4) |
C14A—C15A—C16A—C11A | 0.9 (4) | C14B—C15B—C16B—C11B | 0.9 (4) |
C12A—C11A—C16A—C15A | −0.1 (4) | C12B—C11B—C16B—C15B | −0.5 (4) |
N1A—C11A—C16A—C15A | −176.3 (2) | N1B—C11B—C16B—C15B | −176.2 (2) |
C11A—N1A—C1A—O11A | 10.5 (4) | C11B—N1B—C1B—O11B | 11.9 (5) |
C11A—N1A—C1A—O12A | −167.3 (2) | C11B—N1B—C1B—O12B | −165.8 (2) |
O11A—C1A—O12A—N2A | 9.9 (3) | O11B—C1B—O12B—N2B | 8.9 (4) |
N1A—C1A—O12A—N2A | −172.2 (2) | N1B—C1B—O12B—N2B | −173.2 (2) |
C1A—O12A—N2A—C2A | −164.7 (2) | C1B—O12B—N2B—C2B | −153.3 (2) |
O12A—N2A—C2A—C21A | −175.5 (2) | O12B—N2B—C2B—C21B | −177.8 (2) |
N2A—C2A—C21A—C26A | −173.3 (3) | N2B—C2B—C21B—C22B | 8.7 (4) |
N2A—C2A—C21A—C22A | 8.0 (4) | N2B—C2B—C21B—C26B | −171.6 (3) |
C26A—C21A—C22A—C23A | −0.5 (4) | C26B—C21B—C22B—C23B | 0.3 (4) |
C2A—C21A—C22A—C23A | 178.1 (2) | C2B—C21B—C22B—C23B | 179.9 (2) |
C21A—C22A—C23A—C24A | 0.8 (4) | C21B—C22B—C23B—C24B | 0.1 (4) |
C22A—C23A—C24A—O24A | −179.6 (2) | C22B—C23B—C24B—O24B | −179.5 (2) |
C22A—C23A—C24A—C25A | −0.4 (4) | C22B—C23B—C24B—C25B | −0.3 (4) |
C25A—C24A—O24A—C241 | 1.0 (4) | C25B—C24B—O24B—C242 | 0.0 (4) |
C23A—C24A—O24A—C241 | −179.8 (3) | C23B—C24B—O24B—C242 | 179.2 (2) |
O24A—C24A—C25A—C26A | 178.8 (2) | O24B—C24B—C25B—C26B | 179.2 (2) |
C23A—C24A—C25A—C26A | −0.3 (4) | C23B—C24B—C25B—C26B | 0.1 (4) |
C24A—C25A—C26A—C21A | 0.5 (4) | C24B—C25B—C26B—C21B | 0.3 (4) |
C22A—C21A—C26A—C25A | −0.1 (4) | C22B—C21B—C26B—C25B | −0.5 (4) |
C2A—C21A—C26A—C25A | −178.9 (3) | C2B—C21B—C26B—C25B | 179.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O11B | 0.84 (3) | 2.10 (3) | 2.920 (3) | 165 (3) |
N1B—H1B···O11Ai | 0.84 (3) | 2.16 (3) | 2.993 (3) | 178 (3) |
C12B—H12B···O11B | 1.08 (3) | 2.27 (2) | 2.900 (3) | 115 (2) |
C12A—H12A···O11A | 0.99 (2) | 2.41 (2) | 2.983 (3) | 116 (2) |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C15H14N2O3 |
Mr | 270.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.8037 (8), 12.1484 (15), 12.9823 (17) |
α, β, γ (°) | 75.275 (11), 81.075 (9), 80.746 (9) |
V (Å3) | 1315.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.3 × 0.2 × 0.05 |
|
Data collection |
Diffractometer | Kuma KM-4-CCD four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10887, 5124, 2749 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.128, 0.94 |
No. of reflections | 5124 |
No. of parameters | 456 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.25, −0.28 |
Selected geometric parameters (Å, º) topN1A—C1A | 1.345 (3) | N1B—C1B | 1.350 (3) |
N1A—C11A | 1.419 (3) | N1B—C11B | 1.415 (3) |
C1A—O11A | 1.217 (3) | C1B—O11B | 1.212 (3) |
C1A—O12A | 1.371 (3) | C1B—O12B | 1.369 (3) |
O12A—N2A | 1.442 (3) | O12B—N2B | 1.445 (3) |
N2A—C2A | 1.277 (3) | N2B—C2B | 1.278 (3) |
C2A—C21A | 1.459 (4) | C2B—C21B | 1.466 (4) |
| | | |
C1A—N1A—C11A | 126.9 (3) | C1B—N1B—C11B | 125.6 (2) |
O11A—C1A—N1A | 127.9 (3) | O11B—C1B—N1B | 127.7 (3) |
O11A—C1A—O12A | 124.5 (2) | O11B—C1B—O12B | 124.0 (2) |
N1A—C1A—O12A | 107.6 (2) | N1B—C1B—O12B | 108.3 (2) |
C1A—O12A—N2A | 113.0 (2) | C1B—O12B—N2B | 111.9 (2) |
C2A—N2A—O12A | 107.6 (2) | C2B—N2B—O12B | 107.3 (2) |
N2A—C2A—C21A | 120.5 (3) | N2B—C2B—C21B | 120.4 (3) |
| | | |
C11A—N1A—C1A—O11A | 10.5 (4) | C11B—N1B—C1B—O11B | 11.9 (5) |
C11A—N1A—C1A—O12A | −167.3 (2) | C11B—N1B—C1B—O12B | −165.8 (2) |
O11A—C1A—O12A—N2A | 9.9 (3) | O11B—C1B—O12B—N2B | 8.9 (4) |
N1A—C1A—O12A—N2A | −172.2 (2) | N1B—C1B—O12B—N2B | −173.2 (2) |
C1A—O12A—N2A—C2A | −164.7 (2) | C1B—O12B—N2B—C2B | −153.3 (2) |
O12A—N2A—C2A—C21A | −175.5 (2) | O12B—N2B—C2B—C21B | −177.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O11B | 0.84 (3) | 2.10 (3) | 2.920 (3) | 165 (3) |
N1B—H1B···O11Ai | 0.84 (3) | 2.16 (3) | 2.993 (3) | 178 (3) |
C12B—H12B···O11B | 1.08 (3) | 2.27 (2) | 2.900 (3) | 115 (2) |
C12A—H12A···O11A | 0.99 (2) | 2.41 (2) | 2.983 (3) | 116 (2) |
Symmetry code: (i) x+1, y, z. |
There are some 35 structures of benzaldehyde oxime derivatives in the Cambridge Structural Database (CSD; Version of February 2005; Allen, 2002); however, there are no examples of carbamoyl derivatives. Moreover, there is only one structure, and that is a relatively poorly determined one (R = 9.3%, no H atoms), containing the NH—C(=O)—O—N=C group {[2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyl]oxime; Takusagawa & Jacobson, 1977]. This is even more surprising taking into account that chemical literature dealing with O-phenylcarbamoylated aldoximes is extensive, for example acylation of aldoximes (Hauser et al., 1935; Rainsford & Hauser, 1939) and conversion of aldehydes into nitriles (Coskun & Arikan, 1999). These compounds also have biological activity; for instance, the anelgesic anidoxime has the structure of phenylcarbamoylated oxime (Grainger et al., 1977; Watzman & Buckley, 1980) and aldicarb, [2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyl]oxime, is used as a pesticide.
It therefore seemed interesting to determine the crystal structure of one of the most representative members of this family, the title compound, (I). The asymmetric part of the unit cell contains two molecules (A and B). The normal probability plot analyses (Abrahams & Keve, 1971; International Tables for X-ray Crystallography, 1974, Vol. IV, p. 293) for both bond lengths and bond angles show that the differences between the symmetry-independent molecules are of a statistical nature: the squares of the correlation factors are 0.96 and 0.99 for bond lengths and angles, respectively.
The overall conformation of the molecule of (I) can be described by the dihedral angles between four approximately planar fragments: the phenyl ring, (A), the N(H)COO group, (B), the CC(H)═NO fragment, (C), and the methoxy-substituted phenyl ring, (D). The maximum deviations are no larger than 0.007 (2) Å for the rings and 0.032 (4) Å for fragments (B) and (C). The dihedral angles between the terminal phenyl ring planes, which might serve as a measure of the overall (A)/(B) angle, is 29.7 (1)° in molecule A and 29.2 (1)° in B, the (B)/(C) angles are 21.0 (2)° in A and 30.6 (2)° in B, and finally the (C)/(D) angles in molecules A and B are 10.3 (2) and 9.9 (2)°, respectively.
The bond lengths and angles are typical, with a double C2═N2 bond of 1.278 (3) Å, and the typical asymmetry of C—N bonds around atom N1; for 825 Ph—NH—C(═O)—R fragments found in the CSD (only organic compounds, no fused rings, no errors, R < 0.075) the mean value of the Cphenyl—N bond length is 1.414 (13) Å and that of the N—C(═O) is 1.352 (15) Å.
In both symmetry-independent molecules in the title compound, the oxime group is in a syn (E) conformation (e.g. Ciajolo et al., 1981), as can be seen from the values of the O12—N2—C2—C21 torsion angles of −175.5 (2) and −177.8 (2)°. The conformation along the N—O bond is anti, the values of the C1—O12—N2—C2 torsion angles are close to 180°. It might be noted that a different conformation, syn (C—N—O—C torsion angle close to 0°) is observed exclusively for the compounds in which the oxime fragment is involved in a cyclic environment. For 281 fragments with an acyclic C═N—O—Z (Z = not hydrogen) group there are only four hits with a C═N—O—Z torsion angle smaller than 130°, viz. l-canavanine (Boyar & Marsh, 1982), d-gluconohydroximo-1.5-lactone 1-N-2',3',4',6'-pentabenzoate (Beer & Vasella, 1985), 4-(N-methoxymethylimino)- 2,2-diphenyl-1,3-dioxa-2-borata-1,2,3,4-tetrahydronaphthalene (Kliegel et al., 1989) and (Z)-2-(benzoyl-acinitro)-2-phenyl acetonitrile (Powell et al., 1996). The smallest value of this angle is 97°. Almost 90% of these compounds have an absolute value of the C—N—O—Z torsion angle larger than 160°.
In the crystal structure, the molecules are arranged into infinite –ABAB– ribbons along the [100] direction by means of strong and directional N—H···O hydrogen bonds (Fig. 2 and Table 2). Using graph-set notation (Etter et al., 1990; Bernstein et al., 1995) at the first order there are two dimers (DD), while the most informative is the second-rank graph-set C22(8); additional weak C—H···π contacts and intramolecular C—H···O11 hydrogen bonds may play stabilizing roles in the creation of the pattern.