



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810042364/sj5045sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810042364/sj5045Isup2.hkl |
CCDC reference: 799696
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.119
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C SHFSU01_ALERT_2_C Test not performed. _refine_ls_shift/su_max and _refine_ls_shift/esd_max not present. Absolute value of the parameter shift to su ratio given 0.001 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 4 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 19
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The reaction of 4-nitrobenzohydrazide (0.181 g, 1 mmol) with 4-hydroxybenzaldehyde (0.122 g, 1 mmol) in 50 ml methanol at room temperature afforded the title compound. Single crystals were formed by slow evaporation of the clear solution in air.
The amino H atom was located in a difference Fourier map and refined with N–H = 0.90 (1) Å, and Uiso = 0.08 Å2. Other H atoms were positioned geometrically (C–H = 0.93 Å, O–H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(O).
Recently, medical applications of a number of hydrazone compounds have been reported (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). Structural investigations of several hydrazone derivatives have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). In this paper, we report the structure of the new derivative N'-(4-Hydroxybenzylidene)-4-nitrobenzohydrazide (I).
The whole molecule of (I) is approximately planar, with a mean deviation from the least squares plane through all 21 non-hydrogen atoms of 0.050 (2) Å; the dihedral angle between the C1···C6 and C9···C14 benzene rings is 2.0 (2)°. The bond lengths and angles are comparable to those found in the hydrazone compounds cited above. In the crystal structure, the hydrazone molecules are linked through intermolecular O1–H1···O2 and N2–H2···O4 hydrogen bonds (Table 1), to form two-dimensional layers in the bc plane, as shown in Fig. 2.
For medical applications of hydrazones, see: Ajani et al. (2010); Zhang et al. (2010); Angelusiu et al. (2010). For related structures, see: Huang & Wu (2010); Khaledi et al. (2010); Zhou & Yang (2010); Ji & Lu (2010); Singh & Singh (2010); Ahmad et al. (2010).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C14H11N3O4 | F(000) = 592 |
Mr = 285.26 | Dx = 1.447 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1632 reflections |
a = 7.856 (3) Å | θ = 2.2–26.0° |
b = 13.368 (5) Å | µ = 0.11 mm−1 |
c = 12.527 (5) Å | T = 298 K |
β = 95.748 (4)° | Block, yellow |
V = 1309.0 (9) Å3 | 0.18 × 0.17 × 0.17 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2822 independent reflections |
Radiation source: fine-focus sealed tube | 1736 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 27.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→10 |
Tmin = 0.981, Tmax = 0.982 | k = −17→14 |
7505 measured reflections | l = −16→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1504P] where P = (Fo2 + 2Fc2)/3 |
2822 reflections | (Δ/σ)max < 0.001 |
194 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
C14H11N3O4 | V = 1309.0 (9) Å3 |
Mr = 285.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.856 (3) Å | µ = 0.11 mm−1 |
b = 13.368 (5) Å | T = 298 K |
c = 12.527 (5) Å | 0.18 × 0.17 × 0.17 mm |
β = 95.748 (4)° |
Bruker SMART CCD area-detector diffractometer | 2822 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1736 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.982 | Rint = 0.025 |
7505 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 1 restraint |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.16 e Å−3 |
2822 reflections | Δρmin = −0.16 e Å−3 |
194 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.20526 (19) | −0.05033 (11) | 0.04617 (11) | 0.0433 (4) | |
N2 | 0.2594 (2) | 0.02540 (11) | −0.01727 (11) | 0.0420 (4) | |
N3 | 0.4845 (2) | 0.44506 (12) | −0.22229 (13) | 0.0510 (4) | |
O1 | 0.0039 (2) | −0.46112 (9) | 0.25453 (11) | 0.0598 (4) | |
H1 | −0.0521 | −0.4411 | 0.3021 | 0.090* | |
O2 | 0.17995 (17) | 0.13969 (9) | 0.09997 (10) | 0.0512 (4) | |
O3 | 0.4755 (2) | 0.52833 (11) | −0.18407 (13) | 0.0872 (6) | |
O4 | 0.54671 (18) | 0.42836 (10) | −0.30610 (10) | 0.0603 (4) | |
C1 | 0.1654 (2) | −0.22332 (13) | 0.07612 (14) | 0.0395 (4) | |
C2 | 0.1046 (2) | −0.20626 (13) | 0.17594 (14) | 0.0433 (5) | |
H2A | 0.1006 | −0.1412 | 0.2020 | 0.052* | |
C3 | 0.0511 (2) | −0.28366 (13) | 0.23572 (14) | 0.0444 (5) | |
H3 | 0.0107 | −0.2708 | 0.3017 | 0.053* | |
C4 | 0.0567 (2) | −0.38146 (13) | 0.19834 (14) | 0.0424 (5) | |
C5 | 0.1185 (2) | −0.39987 (13) | 0.10044 (15) | 0.0463 (5) | |
H5 | 0.1240 | −0.4651 | 0.0753 | 0.056* | |
C6 | 0.1721 (2) | −0.32147 (13) | 0.04010 (14) | 0.0446 (5) | |
H6 | 0.2132 | −0.3346 | −0.0256 | 0.053* | |
C7 | 0.2197 (2) | −0.13939 (13) | 0.01282 (14) | 0.0422 (4) | |
H7 | 0.2649 | −0.1512 | −0.0519 | 0.051* | |
C8 | 0.2426 (2) | 0.12013 (13) | 0.01678 (13) | 0.0372 (4) | |
C9 | 0.3070 (2) | 0.20201 (12) | −0.05002 (13) | 0.0352 (4) | |
C10 | 0.2986 (2) | 0.29875 (13) | −0.01120 (14) | 0.0454 (5) | |
H10 | 0.2541 | 0.3099 | 0.0538 | 0.055* | |
C11 | 0.3552 (2) | 0.37861 (13) | −0.06733 (15) | 0.0482 (5) | |
H11 | 0.3492 | 0.4435 | −0.0411 | 0.058* | |
C12 | 0.4209 (2) | 0.36016 (13) | −0.16304 (14) | 0.0395 (4) | |
C13 | 0.4312 (2) | 0.26543 (14) | −0.20412 (14) | 0.0449 (5) | |
H13 | 0.4760 | 0.2548 | −0.2691 | 0.054* | |
C14 | 0.3738 (2) | 0.18647 (13) | −0.14713 (14) | 0.0446 (5) | |
H14 | 0.3799 | 0.1219 | −0.1740 | 0.054* | |
H2 | 0.299 (3) | 0.0083 (16) | −0.0797 (11) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0554 (10) | 0.0363 (9) | 0.0402 (9) | −0.0019 (7) | 0.0149 (7) | 0.0061 (7) |
N2 | 0.0593 (10) | 0.0337 (8) | 0.0360 (8) | −0.0025 (7) | 0.0187 (7) | 0.0034 (7) |
N3 | 0.0596 (11) | 0.0466 (10) | 0.0482 (10) | −0.0082 (8) | 0.0127 (8) | 0.0080 (8) |
O1 | 0.0868 (11) | 0.0365 (7) | 0.0615 (9) | −0.0022 (7) | 0.0338 (8) | 0.0061 (7) |
O2 | 0.0688 (9) | 0.0451 (8) | 0.0442 (8) | 0.0005 (7) | 0.0273 (6) | −0.0002 (6) |
O3 | 0.1470 (17) | 0.0418 (9) | 0.0802 (12) | −0.0201 (10) | 0.0472 (11) | 0.0006 (8) |
O4 | 0.0700 (10) | 0.0636 (9) | 0.0511 (9) | −0.0088 (7) | 0.0247 (7) | 0.0110 (7) |
C1 | 0.0415 (10) | 0.0392 (10) | 0.0385 (10) | 0.0004 (8) | 0.0075 (8) | 0.0030 (8) |
C2 | 0.0554 (11) | 0.0332 (10) | 0.0429 (10) | −0.0023 (8) | 0.0127 (9) | −0.0005 (8) |
C3 | 0.0553 (11) | 0.0411 (10) | 0.0390 (10) | 0.0011 (9) | 0.0154 (9) | −0.0003 (9) |
C4 | 0.0467 (11) | 0.0362 (10) | 0.0453 (11) | 0.0007 (8) | 0.0100 (9) | 0.0077 (9) |
C5 | 0.0585 (12) | 0.0326 (9) | 0.0495 (11) | 0.0012 (9) | 0.0135 (9) | −0.0022 (9) |
C6 | 0.0524 (11) | 0.0432 (11) | 0.0400 (10) | 0.0015 (9) | 0.0142 (9) | −0.0008 (9) |
C7 | 0.0472 (11) | 0.0441 (11) | 0.0367 (10) | −0.0006 (9) | 0.0123 (8) | 0.0042 (9) |
C8 | 0.0394 (10) | 0.0405 (10) | 0.0327 (9) | 0.0025 (8) | 0.0084 (8) | 0.0015 (8) |
C9 | 0.0367 (9) | 0.0369 (9) | 0.0330 (9) | 0.0032 (7) | 0.0083 (7) | 0.0026 (8) |
C10 | 0.0589 (12) | 0.0430 (11) | 0.0373 (10) | −0.0008 (9) | 0.0197 (9) | −0.0045 (8) |
C11 | 0.0632 (12) | 0.0353 (10) | 0.0481 (11) | −0.0029 (9) | 0.0159 (10) | −0.0030 (9) |
C12 | 0.0424 (10) | 0.0371 (10) | 0.0400 (10) | −0.0021 (8) | 0.0088 (8) | 0.0068 (8) |
C13 | 0.0554 (11) | 0.0457 (11) | 0.0363 (10) | 0.0012 (9) | 0.0180 (9) | 0.0024 (9) |
C14 | 0.0605 (12) | 0.0343 (9) | 0.0417 (10) | 0.0032 (9) | 0.0186 (9) | −0.0013 (8) |
N1—C7 | 1.271 (2) | C4—C5 | 1.386 (2) |
N1—N2 | 1.3803 (19) | C5—C6 | 1.382 (2) |
N2—C8 | 1.347 (2) | C5—H5 | 0.9300 |
N2—H2 | 0.899 (9) | C6—H6 | 0.9300 |
N3—O3 | 1.217 (2) | C7—H7 | 0.9300 |
N3—O4 | 1.2220 (19) | C8—C9 | 1.496 (2) |
N3—C12 | 1.471 (2) | C9—C10 | 1.386 (2) |
O1—C4 | 1.364 (2) | C9—C14 | 1.388 (2) |
O1—H1 | 0.8200 | C10—C11 | 1.376 (2) |
O2—C8 | 1.2247 (19) | C10—H10 | 0.9300 |
C1—C6 | 1.390 (2) | C11—C12 | 1.374 (2) |
C1—C2 | 1.401 (2) | C11—H11 | 0.9300 |
C1—C7 | 1.462 (2) | C12—C13 | 1.372 (2) |
C2—C3 | 1.368 (2) | C13—C14 | 1.375 (2) |
C2—H2A | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.391 (2) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | ||
C7—N1—N2 | 117.08 (14) | C1—C6—H6 | 119.5 |
C8—N2—N1 | 117.50 (13) | N1—C7—C1 | 120.02 (15) |
C8—N2—H2 | 124.6 (15) | N1—C7—H7 | 120.0 |
N1—N2—H2 | 117.9 (15) | C1—C7—H7 | 120.0 |
O3—N3—O4 | 123.30 (16) | O2—C8—N2 | 122.05 (15) |
O3—N3—C12 | 118.13 (16) | O2—C8—C9 | 120.45 (15) |
O4—N3—C12 | 118.55 (16) | N2—C8—C9 | 117.49 (14) |
C4—O1—H1 | 109.5 | C10—C9—C14 | 118.85 (15) |
C6—C1—C2 | 118.08 (16) | C10—C9—C8 | 117.14 (14) |
C6—C1—C7 | 121.71 (15) | C14—C9—C8 | 124.01 (15) |
C2—C1—C7 | 120.20 (16) | C11—C10—C9 | 121.04 (16) |
C3—C2—C1 | 121.08 (16) | C11—C10—H10 | 119.5 |
C3—C2—H2A | 119.5 | C9—C10—H10 | 119.5 |
C1—C2—H2A | 119.5 | C12—C11—C10 | 118.37 (17) |
C2—C3—C4 | 120.32 (16) | C12—C11—H11 | 120.8 |
C2—C3—H3 | 119.8 | C10—C11—H11 | 120.8 |
C4—C3—H3 | 119.8 | C13—C12—C11 | 122.28 (16) |
O1—C4—C5 | 118.02 (16) | C13—C12—N3 | 119.15 (15) |
O1—C4—C3 | 122.60 (15) | C11—C12—N3 | 118.56 (16) |
C5—C4—C3 | 119.38 (16) | C12—C13—C14 | 118.62 (15) |
C6—C5—C4 | 120.15 (17) | C12—C13—H13 | 120.7 |
C6—C5—H5 | 119.9 | C14—C13—H13 | 120.7 |
C4—C5—H5 | 119.9 | C13—C14—C9 | 120.83 (16) |
C5—C6—C1 | 120.97 (16) | C13—C14—H14 | 119.6 |
C5—C6—H6 | 119.5 | C9—C14—H14 | 119.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.98 | 2.7841 (18) | 166 |
N2—H2···O4ii | 0.90 (1) | 2.24 (1) | 3.094 (2) | 159 (2) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H11N3O4 |
Mr | 285.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 7.856 (3), 13.368 (5), 12.527 (5) |
β (°) | 95.748 (4) |
V (Å3) | 1309.0 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.18 × 0.17 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.981, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7505, 2822, 1736 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.119, 1.04 |
No. of reflections | 2822 |
No. of parameters | 194 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.16 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.98 | 2.7841 (18) | 165.8 |
N2—H2···O4ii | 0.899 (9) | 2.239 (12) | 3.094 (2) | 158.9 (19) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z−1/2. |
Recently, medical applications of a number of hydrazone compounds have been reported (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). Structural investigations of several hydrazone derivatives have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). In this paper, we report the structure of the new derivative N'-(4-Hydroxybenzylidene)-4-nitrobenzohydrazide (I).
The whole molecule of (I) is approximately planar, with a mean deviation from the least squares plane through all 21 non-hydrogen atoms of 0.050 (2) Å; the dihedral angle between the C1···C6 and C9···C14 benzene rings is 2.0 (2)°. The bond lengths and angles are comparable to those found in the hydrazone compounds cited above. In the crystal structure, the hydrazone molecules are linked through intermolecular O1–H1···O2 and N2–H2···O4 hydrogen bonds (Table 1), to form two-dimensional layers in the bc plane, as shown in Fig. 2.