The asymmetric unit of the title compound, C
14H
13N
3O
3·H
2O, consists of one isonicotinic acid (3-hydroxy-4-methoxybenzylidene)hydrazide (IBH) molecule and one water molecule connected through an O—H
O hydrogen bond. Further O—H
O, O—H
N and N—H
O hydrogen bonds result in the formation of an intricate three-dimensional supramolecular network.
Supporting information
CCDC reference: 289718
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.107
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C6 .. 5.34 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. O3 .. 2.63 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 38.00 A 3
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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
3-Hydroxy-4-methoxybenzaldehyde isonicotinoylhydrazone monohydrate
top
Crystal data top
C14H13N3O3·H2O | F(000) = 608 |
Mr = 289.29 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/n | Melting point: 463 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1684 (16) Å | Cell parameters from 2154 reflections |
b = 11.489 (2) Å | θ = 2.3–26.1° |
c = 13.889 (2) Å | µ = 0.10 mm−1 |
β = 93.688 (3)° | T = 294 K |
V = 1459.9 (4) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.24 × 0.22 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 2977 independent reflections |
Radiation source: fine-focus sealed tube | 1964 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.960, Tmax = 0.979 | k = −11→14 |
8023 measured reflections | l = −17→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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.2089P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2977 reflections | Δρmax = 0.20 e Å−3 |
208 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (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 | |
O1 | 0.25245 (13) | 0.54391 (11) | 0.35715 (9) | 0.0509 (4) | |
O2 | 0.37743 (12) | 0.23613 (10) | 0.75734 (8) | 0.0402 (3) | |
H2A | 0.445 (2) | 0.2509 (18) | 0.7093 (16) | 0.071 (7)* | |
O3 | 0.19327 (11) | 0.11386 (10) | 0.84860 (8) | 0.0405 (3) | |
N1 | −0.0252 (2) | 0.64113 (14) | 0.04566 (11) | 0.0571 (5) | |
N2 | 0.05144 (16) | 0.43202 (12) | 0.36601 (9) | 0.0357 (3) | |
H2B | −0.022 (2) | 0.4017 (15) | 0.3379 (13) | 0.046 (5)* | |
N3 | 0.10256 (14) | 0.38462 (12) | 0.45344 (9) | 0.0351 (3) | |
C1 | −0.1161 (2) | 0.59263 (16) | 0.10464 (13) | 0.0484 (5) | |
H1 | −0.2147 | 0.5887 | 0.0845 | 0.058* | |
C2 | −0.07281 (19) | 0.54760 (14) | 0.19418 (12) | 0.0387 (4) | |
H2 | −0.1410 | 0.5148 | 0.2329 | 0.046* | |
C3 | 0.07319 (17) | 0.55192 (14) | 0.22544 (11) | 0.0349 (4) | |
C4 | 0.1685 (2) | 0.60190 (18) | 0.16418 (13) | 0.0540 (5) | |
H4 | 0.2678 | 0.6070 | 0.1822 | 0.065* | |
C5 | 0.1146 (3) | 0.64386 (19) | 0.07656 (15) | 0.0643 (6) | |
H5 | 0.1805 | 0.6764 | 0.0361 | 0.077* | |
C6 | 0.13380 (18) | 0.50909 (14) | 0.32213 (11) | 0.0347 (4) | |
C7 | 0.01520 (18) | 0.31528 (15) | 0.49196 (11) | 0.0356 (4) | |
H7 | −0.0764 | 0.3006 | 0.4618 | 0.043* | |
C8 | 0.05851 (17) | 0.25851 (14) | 0.58365 (11) | 0.0319 (4) | |
C9 | 0.19995 (16) | 0.27350 (14) | 0.62581 (10) | 0.0305 (4) | |
H9 | 0.2669 | 0.3180 | 0.5943 | 0.037* | |
C10 | 0.24122 (16) | 0.22342 (13) | 0.71308 (10) | 0.0293 (4) | |
C11 | 0.13994 (17) | 0.15794 (14) | 0.76210 (11) | 0.0316 (4) | |
C12 | 0.00052 (17) | 0.14190 (15) | 0.72068 (12) | 0.0387 (4) | |
H12 | −0.0668 | 0.0979 | 0.7524 | 0.046* | |
C13 | −0.03922 (17) | 0.19167 (15) | 0.63133 (12) | 0.0393 (4) | |
H13 | −0.1329 | 0.1797 | 0.6034 | 0.047* | |
C14 | 0.09332 (19) | 0.05221 (16) | 0.90501 (12) | 0.0459 (5) | |
H14A | 0.0143 | 0.1028 | 0.9194 | 0.069* | |
H14B | 0.1433 | 0.0264 | 0.9641 | 0.069* | |
H14C | 0.0554 | −0.0139 | 0.8694 | 0.069* | |
O4 | 0.57840 (15) | 0.25477 (16) | 0.63487 (11) | 0.0563 (4) | |
H4A | 0.573 (3) | 0.219 (2) | 0.578 (2) | 0.102 (10)* | |
H4B | 0.632 (3) | 0.309 (2) | 0.6328 (16) | 0.074 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0400 (7) | 0.0593 (8) | 0.0516 (8) | −0.0145 (6) | −0.0107 (6) | 0.0089 (6) |
O2 | 0.0295 (6) | 0.0576 (8) | 0.0324 (6) | −0.0056 (5) | −0.0064 (5) | 0.0103 (6) |
O3 | 0.0378 (7) | 0.0512 (7) | 0.0318 (6) | −0.0028 (5) | −0.0014 (5) | 0.0157 (5) |
N1 | 0.0800 (13) | 0.0556 (11) | 0.0352 (9) | 0.0111 (9) | 0.0009 (9) | 0.0103 (8) |
N2 | 0.0364 (8) | 0.0417 (8) | 0.0273 (7) | −0.0089 (7) | −0.0106 (6) | 0.0070 (6) |
N3 | 0.0373 (8) | 0.0415 (8) | 0.0254 (7) | −0.0013 (6) | −0.0074 (6) | 0.0056 (6) |
C1 | 0.0571 (12) | 0.0447 (11) | 0.0420 (10) | 0.0059 (9) | −0.0072 (9) | 0.0044 (9) |
C2 | 0.0454 (10) | 0.0366 (10) | 0.0334 (9) | 0.0005 (8) | −0.0019 (7) | 0.0049 (7) |
C3 | 0.0431 (10) | 0.0313 (9) | 0.0300 (8) | 0.0011 (7) | 0.0004 (7) | 0.0011 (7) |
C4 | 0.0499 (11) | 0.0663 (13) | 0.0463 (11) | −0.0045 (10) | 0.0061 (9) | 0.0169 (10) |
C5 | 0.0725 (16) | 0.0729 (15) | 0.0491 (12) | −0.0001 (12) | 0.0155 (11) | 0.0226 (11) |
C6 | 0.0357 (9) | 0.0360 (9) | 0.0317 (9) | 0.0016 (7) | −0.0019 (7) | −0.0005 (7) |
C7 | 0.0312 (9) | 0.0440 (10) | 0.0305 (8) | −0.0009 (8) | −0.0052 (7) | 0.0028 (7) |
C8 | 0.0314 (9) | 0.0359 (9) | 0.0277 (8) | 0.0025 (7) | −0.0025 (7) | 0.0025 (7) |
C9 | 0.0307 (8) | 0.0342 (9) | 0.0265 (8) | −0.0021 (7) | 0.0013 (6) | 0.0025 (7) |
C10 | 0.0265 (8) | 0.0342 (9) | 0.0266 (8) | 0.0024 (7) | −0.0024 (6) | −0.0008 (7) |
C11 | 0.0338 (9) | 0.0350 (9) | 0.0258 (8) | 0.0049 (7) | 0.0002 (7) | 0.0032 (7) |
C12 | 0.0322 (9) | 0.0442 (10) | 0.0398 (10) | −0.0045 (7) | 0.0031 (7) | 0.0103 (8) |
C13 | 0.0267 (9) | 0.0509 (11) | 0.0392 (10) | −0.0022 (7) | −0.0055 (7) | 0.0067 (8) |
C14 | 0.0493 (11) | 0.0494 (11) | 0.0393 (10) | −0.0021 (9) | 0.0053 (8) | 0.0176 (8) |
O4 | 0.0458 (8) | 0.0724 (11) | 0.0520 (9) | −0.0228 (8) | 0.0130 (7) | −0.0165 (8) |
Geometric parameters (Å, º) top
O1—C6 | 1.2297 (18) | C5—H5 | 0.9300 |
O2—C10 | 1.3637 (18) | C7—C8 | 1.463 (2) |
O3—C11 | 1.3650 (17) | C7—H7 | 0.9300 |
O3—C14 | 1.4310 (19) | C8—C13 | 1.381 (2) |
N1—C5 | 1.326 (3) | C8—C9 | 1.399 (2) |
N1—C1 | 1.328 (2) | C9—C10 | 1.373 (2) |
N2—C6 | 1.336 (2) | C9—H9 | 0.9300 |
N2—N3 | 1.3847 (17) | C10—C11 | 1.405 (2) |
N2—H2B | 0.832 (19) | C11—C12 | 1.380 (2) |
N3—C7 | 1.272 (2) | C12—C13 | 1.393 (2) |
C1—C2 | 1.381 (2) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.381 (2) | C14—H14A | 0.9600 |
C2—H2 | 0.9300 | C14—H14B | 0.9600 |
C3—C4 | 1.383 (2) | C14—H14C | 0.9600 |
C3—C6 | 1.503 (2) | O4—H4A | 0.88 (3) |
C4—C5 | 1.371 (3) | O4—H4B | 0.79 (3) |
C4—H4 | 0.9300 | | |
| | | |
C10—O2—H2A | 108.5 (13) | C8—C7—H7 | 119.9 |
C11—O3—C14 | 117.37 (12) | C13—C8—C9 | 118.71 (14) |
C5—N1—C1 | 116.24 (16) | C13—C8—C7 | 121.14 (14) |
C6—N2—N3 | 119.43 (14) | C9—C8—C7 | 120.13 (14) |
C6—N2—H2B | 121.8 (12) | C10—C9—C8 | 120.90 (14) |
N3—N2—H2B | 117.7 (12) | C10—C9—H9 | 119.6 |
C7—N3—N2 | 115.37 (13) | C8—C9—H9 | 119.6 |
N1—C1—C2 | 123.88 (18) | O2—C10—C9 | 123.06 (14) |
N1—C1—H1 | 118.1 | O2—C10—C11 | 116.98 (13) |
C2—C1—H1 | 118.1 | C9—C10—C11 | 119.94 (14) |
C1—C2—C3 | 119.07 (17) | O3—C11—C12 | 125.96 (14) |
C1—C2—H2 | 120.5 | O3—C11—C10 | 114.50 (13) |
C3—C2—H2 | 120.5 | C12—C11—C10 | 119.54 (14) |
C2—C3—C4 | 117.36 (15) | C11—C12—C13 | 119.91 (15) |
C2—C3—C6 | 124.35 (15) | C11—C12—H12 | 120.0 |
C4—C3—C6 | 118.27 (15) | C13—C12—H12 | 120.0 |
C5—C4—C3 | 119.07 (19) | C8—C13—C12 | 120.97 (15) |
C5—C4—H4 | 120.5 | C8—C13—H13 | 119.5 |
C3—C4—H4 | 120.5 | C12—C13—H13 | 119.5 |
N1—C5—C4 | 124.38 (19) | O3—C14—H14A | 109.5 |
N1—C5—H5 | 117.8 | O3—C14—H14B | 109.5 |
C4—C5—H5 | 117.8 | H14A—C14—H14B | 109.5 |
O1—C6—N2 | 123.15 (15) | O3—C14—H14C | 109.5 |
O1—C6—C3 | 120.92 (15) | H14A—C14—H14C | 109.5 |
N2—C6—C3 | 115.93 (14) | H14B—C14—H14C | 109.5 |
N3—C7—C8 | 120.16 (14) | H4A—O4—H4B | 109 (2) |
N3—C7—H7 | 119.9 | | |
| | | |
C6—N2—N3—C7 | 177.55 (15) | N3—C7—C8—C9 | −4.7 (2) |
C5—N1—C1—C2 | 0.7 (3) | C13—C8—C9—C10 | −0.3 (2) |
N1—C1—C2—C3 | −0.3 (3) | C7—C8—C9—C10 | 178.24 (15) |
C1—C2—C3—C4 | 0.0 (2) | C8—C9—C10—O2 | −179.57 (14) |
C1—C2—C3—C6 | 178.27 (16) | C8—C9—C10—C11 | −1.2 (2) |
C2—C3—C4—C5 | −0.2 (3) | C14—O3—C11—C12 | −4.7 (2) |
C6—C3—C4—C5 | −178.53 (18) | C14—O3—C11—C10 | 176.31 (14) |
C1—N1—C5—C4 | −0.9 (3) | O2—C10—C11—O3 | −0.8 (2) |
C3—C4—C5—N1 | 0.7 (3) | C9—C10—C11—O3 | −179.20 (14) |
N3—N2—C6—O1 | −2.6 (2) | O2—C10—C11—C12 | −179.82 (14) |
N3—N2—C6—C3 | 177.24 (13) | C9—C10—C11—C12 | 1.7 (2) |
C2—C3—C6—O1 | −158.92 (16) | O3—C11—C12—C13 | −179.65 (16) |
C4—C3—C6—O1 | 19.3 (2) | C10—C11—C12—C13 | −0.7 (2) |
C2—C3—C6—N2 | 21.3 (2) | C9—C8—C13—C12 | 1.3 (2) |
C4—C3—C6—N2 | −160.52 (16) | C7—C8—C13—C12 | −177.18 (16) |
N2—N3—C7—C8 | 179.00 (14) | C11—C12—C13—C8 | −0.8 (3) |
N3—C7—C8—C13 | 173.81 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O4 | 0.95 (2) | 1.66 (2) | 2.5956 (18) | 169 (2) |
N2—H2B···O2i | 0.832 (19) | 2.116 (19) | 2.8715 (19) | 150.9 (17) |
N2—H2B···O3i | 0.832 (19) | 2.631 (18) | 3.3193 (19) | 141.0 (16) |
O4—H4A···N1ii | 0.88 (3) | 1.97 (3) | 2.841 (2) | 170 (3) |
O4—H4B···O1iii | 0.79 (3) | 2.00 (3) | 2.783 (2) | 171 (2) |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1. |