The molecule of the title compound, C
14H
11N
3O
5, is approximately planar, the dihedral angles between the two aromatic rings being 4.63 (7)°. O—H
N, N—H
O and O—H
O hydrogen bonds and π–π stacking interactions help to consolidate the crystal packing.
Supporting information
CCDC reference: 613700
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.131
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1288.60 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT414_ALERT_2_C Short Intra D-H..H-X H2B .. H14A .. 1.98 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.
5-Nitrosalicylaldehyde (2-hydroxybenzoyl)hydrazone
top
Crystal data top
C14H11N3O5 | F(000) = 624 |
Mr = 301.26 | Dx = 1.553 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2939 reflections |
a = 7.645 (3) Å | θ = 3.1–27.5° |
b = 6.751 (3) Å | µ = 0.12 mm−1 |
c = 24.994 (11) Å | T = 293 K |
β = 92.473 (9)° | Chip, colorless |
V = 1288.6 (9) Å3 | 0.40 × 0.15 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku Weissenberg IP diffractometer | 2939 independent reflections |
Radiation source: fine-focus sealed tube | 2101 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: ψ scan (TEXRAY; Molecular Structure Corporation, 1999) | h = −9→9 |
Tmin = 0.978, Tmax = 0.988 | k = −8→8 |
11290 measured reflections | l = −32→31 |
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)] = 0.040 | Hydrogen site location: difmap and geom |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0809P)2] where P = (Fo2 + 2Fc2)/3 |
2939 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | |
C1 | 0.28834 (18) | 0.6284 (2) | 0.12442 (6) | 0.0373 (3) | |
C2 | 0.32468 (18) | 0.7406 (2) | 0.07870 (5) | 0.0358 (3) | |
C3 | 0.39886 (18) | 0.9272 (2) | 0.08554 (6) | 0.0368 (3) | |
H3A | 0.4221 | 1.0043 | 0.0559 | 0.053 (5)* | |
C4 | 0.43803 (18) | 0.9981 (2) | 0.13654 (5) | 0.0353 (3) | |
C5 | 0.40496 (19) | 0.8872 (2) | 0.18154 (6) | 0.0402 (3) | |
H5A | 0.4331 | 0.9364 | 0.2156 | 0.059 (5)* | |
C6 | 0.3304 (2) | 0.7042 (2) | 0.17522 (6) | 0.0426 (4) | |
H6A | 0.3073 | 0.6291 | 0.2053 | 0.061 (5)* | |
C7 | 0.2908 (2) | 0.6683 (2) | 0.02415 (6) | 0.0421 (4) | |
H7A | 0.3118 | 0.7510 | −0.0046 | 0.061 (5)* | |
C8 | 0.16326 (19) | 0.2517 (2) | −0.04980 (5) | 0.0377 (3) | |
C9 | 0.14129 (18) | 0.1995 (2) | −0.10724 (6) | 0.0362 (3) | |
C10 | 0.07759 (19) | 0.0103 (2) | −0.12123 (6) | 0.0400 (3) | |
C11 | 0.0585 (2) | −0.0422 (3) | −0.17506 (7) | 0.0497 (4) | |
H11A | 0.0149 | −0.1666 | −0.1845 | 0.067 (6)* | |
C12 | 0.1034 (2) | 0.0881 (3) | −0.21415 (6) | 0.0504 (4) | |
H12A | 0.0899 | 0.0513 | −0.2500 | 0.059 (5)* | |
C13 | 0.1685 (2) | 0.2734 (3) | −0.20104 (6) | 0.0489 (4) | |
H13A | 0.2002 | 0.3603 | −0.2278 | 0.051 (5)* | |
C14 | 0.1860 (2) | 0.3287 (2) | −0.14807 (6) | 0.0435 (4) | |
H14A | 0.2285 | 0.4542 | −0.1393 | 0.060 (6)* | |
N1 | 0.23313 (17) | 0.4939 (2) | 0.01539 (5) | 0.0415 (3) | |
N2 | 0.20856 (19) | 0.4402 (2) | −0.03749 (5) | 0.0456 (3) | |
H2B | 0.2219 | 0.5258 | −0.0625 | 0.055 (6)* | |
N3 | 0.52248 (17) | 1.1896 (2) | 0.14243 (5) | 0.0419 (3) | |
O1 | 0.21312 (15) | 0.44866 (17) | 0.12172 (5) | 0.0489 (3) | |
H1B | 0.1822 | 0.4172 | 0.0880 | 0.078 (7)* | |
O2 | 0.1422 (2) | 0.12946 (19) | −0.01428 (4) | 0.0609 (4) | |
O3 | 0.54438 (19) | 1.26019 (18) | 0.18736 (5) | 0.0600 (4) | |
O4 | 0.57015 (17) | 1.27376 (18) | 0.10198 (5) | 0.0559 (3) | |
O5 | 0.03168 (18) | −0.12711 (18) | −0.08534 (5) | 0.0566 (3) | |
H5B | 0.0375 | −0.0700 | −0.0508 | 0.075 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0372 (6) | 0.0344 (8) | 0.0405 (7) | −0.0005 (6) | 0.0018 (6) | 0.0009 (6) |
C2 | 0.0397 (7) | 0.0348 (8) | 0.0326 (7) | 0.0006 (6) | 0.0001 (5) | −0.0017 (6) |
C3 | 0.0447 (7) | 0.0341 (8) | 0.0317 (7) | −0.0020 (6) | 0.0022 (6) | 0.0011 (5) |
C4 | 0.0382 (7) | 0.0320 (7) | 0.0356 (7) | 0.0003 (6) | 0.0001 (6) | −0.0040 (6) |
C5 | 0.0462 (7) | 0.0425 (9) | 0.0318 (7) | 0.0023 (7) | 0.0007 (6) | −0.0038 (6) |
C6 | 0.0496 (8) | 0.0452 (9) | 0.0332 (7) | −0.0030 (7) | 0.0049 (6) | 0.0055 (6) |
C7 | 0.0541 (8) | 0.0364 (8) | 0.0354 (7) | −0.0047 (7) | −0.0012 (6) | −0.0010 (6) |
C8 | 0.0443 (7) | 0.0354 (7) | 0.0331 (7) | −0.0053 (6) | −0.0021 (6) | −0.0008 (6) |
C9 | 0.0380 (6) | 0.0355 (8) | 0.0348 (7) | −0.0018 (6) | −0.0035 (6) | −0.0020 (6) |
C10 | 0.0431 (7) | 0.0364 (8) | 0.0404 (8) | −0.0004 (6) | −0.0019 (6) | −0.0039 (6) |
C11 | 0.0570 (9) | 0.0465 (10) | 0.0449 (9) | −0.0001 (8) | −0.0042 (7) | −0.0126 (7) |
C12 | 0.0545 (9) | 0.0622 (11) | 0.0342 (8) | 0.0070 (8) | −0.0013 (7) | −0.0098 (7) |
C13 | 0.0505 (8) | 0.0612 (11) | 0.0350 (8) | −0.0018 (8) | 0.0019 (6) | 0.0058 (7) |
C14 | 0.0479 (8) | 0.0435 (9) | 0.0387 (8) | −0.0052 (7) | −0.0016 (6) | 0.0017 (7) |
N1 | 0.0525 (7) | 0.0386 (7) | 0.0328 (6) | −0.0045 (6) | −0.0035 (5) | −0.0045 (5) |
N2 | 0.0691 (8) | 0.0368 (7) | 0.0304 (6) | −0.0116 (7) | −0.0034 (6) | −0.0012 (5) |
N3 | 0.0473 (7) | 0.0360 (7) | 0.0421 (7) | −0.0006 (6) | −0.0021 (6) | −0.0049 (5) |
O1 | 0.0582 (6) | 0.0382 (6) | 0.0501 (7) | −0.0121 (5) | −0.0013 (5) | 0.0034 (5) |
O2 | 0.1014 (10) | 0.0455 (7) | 0.0354 (6) | −0.0254 (7) | −0.0025 (6) | 0.0031 (5) |
O3 | 0.0871 (9) | 0.0458 (7) | 0.0459 (7) | −0.0064 (7) | −0.0101 (6) | −0.0145 (6) |
O4 | 0.0710 (8) | 0.0443 (7) | 0.0529 (7) | −0.0184 (6) | 0.0092 (6) | −0.0018 (5) |
O5 | 0.0843 (9) | 0.0389 (7) | 0.0466 (7) | −0.0168 (6) | 0.0021 (6) | −0.0033 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.3430 (19) | C9—C14 | 1.396 (2) |
C1—C6 | 1.394 (2) | C9—C10 | 1.405 (2) |
C1—C2 | 1.409 (2) | C10—O5 | 1.348 (2) |
C2—C3 | 1.389 (2) | C10—C11 | 1.393 (2) |
C2—C7 | 1.461 (2) | C11—C12 | 1.370 (3) |
C3—C4 | 1.382 (2) | C11—H11A | 0.9300 |
C3—H3A | 0.9300 | C12—C13 | 1.380 (3) |
C4—C5 | 1.383 (2) | C12—H12A | 0.9300 |
C4—N3 | 1.450 (2) | C13—C14 | 1.377 (2) |
C5—C6 | 1.366 (2) | C13—H13A | 0.9300 |
C5—H5A | 0.9300 | C14—H14A | 0.9300 |
C6—H6A | 0.9300 | N1—N2 | 1.3755 (17) |
C7—N1 | 1.273 (2) | N2—H2B | 0.8600 |
C7—H7A | 0.9300 | N3—O3 | 1.2248 (17) |
C8—O2 | 1.2277 (19) | N3—O4 | 1.2287 (18) |
C8—N2 | 1.351 (2) | O1—H1B | 0.8903 |
C8—C9 | 1.481 (2) | O5—H5B | 0.9460 |
| | | |
O1—C1—C6 | 117.34 (14) | C10—C9—C8 | 118.75 (13) |
O1—C1—C2 | 122.96 (13) | O5—C10—C11 | 116.62 (15) |
C6—C1—C2 | 119.71 (14) | O5—C10—C9 | 123.88 (14) |
C3—C2—C1 | 118.79 (13) | C11—C10—C9 | 119.51 (15) |
C3—C2—C7 | 118.23 (13) | C12—C11—C10 | 120.42 (16) |
C1—C2—C7 | 122.97 (14) | C12—C11—H11A | 119.8 |
C4—C3—C2 | 119.90 (13) | C10—C11—H11A | 119.8 |
C4—C3—H3A | 120.0 | C11—C12—C13 | 120.77 (15) |
C2—C3—H3A | 120.0 | C11—C12—H12A | 119.6 |
C3—C4—C5 | 121.51 (14) | C13—C12—H12A | 119.6 |
C3—C4—N3 | 118.69 (13) | C14—C13—C12 | 119.55 (16) |
C5—C4—N3 | 119.75 (12) | C14—C13—H13A | 120.2 |
C6—C5—C4 | 119.02 (13) | C12—C13—H13A | 120.2 |
C6—C5—H5A | 120.5 | C13—C14—C9 | 121.13 (16) |
C4—C5—H5A | 120.5 | C13—C14—H14A | 119.4 |
C5—C6—C1 | 121.06 (14) | C9—C14—H14A | 119.4 |
C5—C6—H6A | 119.5 | C7—N1—N2 | 116.18 (13) |
C1—C6—H6A | 119.5 | C8—N2—N1 | 119.36 (13) |
N1—C7—C2 | 121.06 (14) | C8—N2—H2B | 120.3 |
N1—C7—H7A | 119.5 | N1—N2—H2B | 120.3 |
C2—C7—H7A | 119.5 | O3—N3—O4 | 122.74 (14) |
O2—C8—N2 | 120.58 (13) | O3—N3—C4 | 118.87 (13) |
O2—C8—C9 | 121.89 (14) | O4—N3—C4 | 118.39 (12) |
N2—C8—C9 | 117.53 (13) | C1—O1—H1B | 111.0 |
C14—C9—C10 | 118.60 (14) | C10—O5—H5B | 108.9 |
C14—C9—C8 | 122.62 (14) | | |
| | | |
O1—C1—C2—C3 | 178.43 (13) | C14—C9—C10—O5 | 179.44 (15) |
C6—C1—C2—C3 | −1.3 (2) | C8—C9—C10—O5 | 1.2 (2) |
O1—C1—C2—C7 | −2.7 (2) | C14—C9—C10—C11 | −0.9 (2) |
C6—C1—C2—C7 | 177.55 (14) | C8—C9—C10—C11 | −179.10 (14) |
C1—C2—C3—C4 | 1.0 (2) | O5—C10—C11—C12 | −179.47 (16) |
C7—C2—C3—C4 | −177.91 (14) | C9—C10—C11—C12 | 0.9 (2) |
C2—C3—C4—C5 | 0.0 (2) | C10—C11—C12—C13 | 0.1 (3) |
C2—C3—C4—N3 | 177.30 (12) | C11—C12—C13—C14 | −0.9 (3) |
C3—C4—C5—C6 | −0.6 (2) | C12—C13—C14—C9 | 0.8 (2) |
N3—C4—C5—C6 | −177.92 (13) | C10—C9—C14—C13 | 0.1 (2) |
C4—C5—C6—C1 | 0.3 (2) | C8—C9—C14—C13 | 178.19 (14) |
O1—C1—C6—C5 | −179.07 (14) | C2—C7—N1—N2 | −179.01 (14) |
C2—C1—C6—C5 | 0.7 (2) | O2—C8—N2—N1 | 0.8 (2) |
C3—C2—C7—N1 | 175.65 (14) | C9—C8—N2—N1 | −178.92 (13) |
C1—C2—C7—N1 | −3.2 (2) | C7—N1—N2—C8 | 173.89 (14) |
O2—C8—C9—C14 | −171.62 (15) | C3—C4—N3—O3 | 174.07 (14) |
N2—C8—C9—C14 | 8.1 (2) | C5—C4—N3—O3 | −8.5 (2) |
O2—C8—C9—C10 | 6.5 (2) | C3—C4—N3—O4 | −6.4 (2) |
N2—C8—C9—C10 | −173.81 (13) | C5—C4—N3—O4 | 171.01 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O4i | 0.86 | 2.34 | 3.070 (2) | 143 |
O1—H1B···N1 | 0.89 | 1.94 | 2.686 (2) | 140 |
O1—H1B···O5ii | 0.89 | 2.55 | 2.9822 (18) | 111 |
O5—H5B···O2 | 0.95 | 1.79 | 2.5960 (17) | 141 |
O5—H5B···O2ii | 0.95 | 2.21 | 2.873 (2) | 126 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y, −z. |