Crystals of the title compound, C14H12N4O4, were obtained from a condensation reaction of acetophenone and 2,4-dinitrophenylhydrazine. The molecule exhibits a planar structure, with the p-nitro group slightly inclined to the plane. A delocalized double bond is observed in the hydrazone moiety. The separation distances, 3.404 (2) and 3.416 (4) Å, between adjacent parallel phenyl rings indicate π–π aromatic stacking interactions.
Supporting information
CCDC reference: 202315
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.142
- Data-to-parameter ratio = 13.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
2,4-Dinitrophenylhydrazine (0.4 g, 0.2 mmol) was dissolved in ethanol (10 ml), then H2SO4 solution (98%, 0.5 ml) was added slowly to the ethanol solution with stirring. The solution was heated at about 333 K for several minutes until the solution cleared. Acetophenone (0.24 g, 0.2 mmol) was slowly dropped into the solution with continuous stirring, and the mixture solution was kept at about 333 K for 30 min. When the solution had cooled to room temperature, red powdery crystals appeared. The powdery crystals were separated from the solution and washed with water three times. Recrystallization was performed twice, from chloroform and acetone, respectively, to obtain well shaped crystals.
Guided by a difference Fourier map, the methyl H atoms were placed in calculated positions, with C—H = 0.96 Å. A torsional parameter was refined for the methyl group. Other H atoms were placed in calculated positions, with C—H = 0.93 Å and N—H = 0.86 Å; H atoms were included in the final cycles of refinement in the riding mode, with isotropic displacement parameters of 1.2Ueq of the carrier atoms.
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C14H12N4O4 | F(000) = 624 |
Mr = 300.28 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 7.0169 (15) Å | Cell parameters from 24 reflections |
b = 13.263 (3) Å | θ = 5.7–12.3° |
c = 14.8568 (19) Å | µ = 0.11 mm−1 |
β = 97.938 (16)° | T = 298 K |
V = 1369.4 (5) Å3 | Prism, orange |
Z = 4 | 0.42 × 0.32 × 0.22 mm |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.025 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.1° |
Graphite monochromator | h = 0→8 |
ω/2θ scans | k = 0→16 |
2921 measured reflections | l = −18→18 |
2694 independent reflections | 3 standard reflections every 150 reflections |
1212 reflections with I > 2σ(I) | intensity decay: 0.7% |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
2694 reflections | Δρmax = 0.17 e Å−3 |
201 parameters | Δρmin = −0.15 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: 0.0070 (14) |
Crystal data top
C14H12N4O4 | V = 1369.4 (5) Å3 |
Mr = 300.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.0169 (15) Å | µ = 0.11 mm−1 |
b = 13.263 (3) Å | T = 298 K |
c = 14.8568 (19) Å | 0.42 × 0.32 × 0.22 mm |
β = 97.938 (16)° | |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.025 |
2921 measured reflections | 3 standard reflections every 150 reflections |
2694 independent reflections | intensity decay: 0.7% |
1212 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.17 e Å−3 |
2694 reflections | Δρmin = −0.15 e Å−3 |
201 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 | |
O1 | 0.7430 (3) | 0.37165 (15) | 0.12068 (13) | 0.0843 (7) | |
O2 | 0.8323 (3) | 0.22288 (14) | 0.16448 (12) | 0.0739 (6) | |
O3 | 0.5543 (3) | 0.45323 (17) | −0.18725 (15) | 0.0947 (7) | |
O4 | 0.4407 (4) | 0.33706 (18) | −0.28025 (15) | 0.1042 (9) | |
N1 | 0.7623 (3) | 0.28222 (17) | 0.10492 (14) | 0.0583 (6) | |
N2 | 0.5239 (4) | 0.3645 (2) | −0.20664 (17) | 0.0695 (7) | |
N3 | 0.7724 (3) | 0.07074 (14) | 0.05312 (13) | 0.0525 (6) | |
H1 | 0.8091 | 0.0879 | 0.1086 | 0.063* | |
N4 | 0.7777 (3) | −0.02839 (14) | 0.02828 (13) | 0.0503 (5) | |
C1 | 0.7099 (3) | 0.14191 (18) | −0.00903 (15) | 0.0452 (6) | |
C2 | 0.7036 (3) | 0.24505 (18) | 0.01353 (14) | 0.0458 (6) | |
C3 | 0.6425 (3) | 0.31752 (18) | −0.05165 (17) | 0.0501 (6) | |
H3 | 0.6406 | 0.3853 | −0.0359 | 0.060* | |
C4 | 0.5853 (3) | 0.28758 (19) | −0.13908 (16) | 0.0511 (6) | |
C5 | 0.5862 (4) | 0.1867 (2) | −0.16370 (17) | 0.0559 (7) | |
H5 | 0.5460 | 0.1680 | −0.2236 | 0.067* | |
C6 | 0.6456 (3) | 0.11521 (19) | −0.10039 (16) | 0.0513 (6) | |
H6 | 0.6439 | 0.0477 | −0.1174 | 0.062* | |
C7 | 0.8440 (3) | −0.09124 (18) | 0.09082 (16) | 0.0481 (6) | |
C8 | 0.9139 (4) | −0.0606 (2) | 0.18686 (17) | 0.0740 (9) | |
H8C | 0.9744 | −0.1172 | 0.2195 | 0.089* | |
H8A | 0.8070 | −0.0384 | 0.2156 | 0.089* | |
H8B | 1.0053 | −0.0067 | 0.1869 | 0.089* | |
C9 | 0.8441 (3) | −0.19816 (18) | 0.06226 (17) | 0.0481 (6) | |
C10 | 0.8947 (4) | −0.2760 (2) | 0.12382 (18) | 0.0599 (7) | |
H10 | 0.9339 | −0.2611 | 0.1847 | 0.072* | |
C11 | 0.8870 (4) | −0.3757 (2) | 0.0952 (2) | 0.0744 (9) | |
H11 | 0.9206 | −0.4271 | 0.1370 | 0.089* | |
C12 | 0.8307 (4) | −0.3987 (2) | 0.0064 (2) | 0.0731 (9) | |
H12 | 0.8249 | −0.4657 | −0.0123 | 0.088* | |
C13 | 0.7824 (4) | −0.3230 (2) | −0.0559 (2) | 0.0684 (8) | |
H13 | 0.7456 | −0.3388 | −0.1168 | 0.082* | |
C14 | 0.7885 (4) | −0.22388 (19) | −0.02818 (17) | 0.0558 (7) | |
H14 | 0.7549 | −0.1733 | −0.0707 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1326 (19) | 0.0518 (12) | 0.0661 (12) | 0.0023 (12) | 0.0052 (12) | −0.0176 (10) |
O2 | 0.1090 (15) | 0.0635 (12) | 0.0453 (10) | 0.0068 (11) | −0.0029 (10) | −0.0029 (10) |
O3 | 0.130 (2) | 0.0630 (15) | 0.0876 (16) | −0.0036 (13) | 0.0046 (14) | 0.0187 (12) |
O4 | 0.136 (2) | 0.1055 (18) | 0.0609 (13) | 0.0096 (15) | −0.0243 (14) | 0.0121 (13) |
N1 | 0.0715 (15) | 0.0524 (13) | 0.0507 (13) | −0.0041 (12) | 0.0080 (11) | −0.0059 (12) |
N2 | 0.0768 (17) | 0.0712 (17) | 0.0598 (15) | 0.0038 (14) | 0.0071 (12) | 0.0134 (14) |
N3 | 0.0682 (15) | 0.0466 (12) | 0.0424 (11) | 0.0010 (10) | 0.0067 (10) | −0.0023 (10) |
N4 | 0.0570 (13) | 0.0453 (12) | 0.0489 (12) | −0.0008 (10) | 0.0085 (10) | −0.0032 (10) |
C1 | 0.0440 (14) | 0.0466 (14) | 0.0460 (13) | −0.0035 (11) | 0.0105 (11) | −0.0032 (12) |
C2 | 0.0487 (14) | 0.0483 (14) | 0.0403 (12) | −0.0042 (11) | 0.0062 (11) | −0.0039 (11) |
C3 | 0.0530 (15) | 0.0432 (14) | 0.0549 (15) | −0.0033 (12) | 0.0107 (13) | −0.0025 (12) |
C4 | 0.0499 (15) | 0.0563 (16) | 0.0468 (14) | −0.0023 (12) | 0.0059 (12) | 0.0086 (13) |
C5 | 0.0589 (17) | 0.0650 (18) | 0.0425 (14) | −0.0063 (14) | 0.0030 (12) | −0.0035 (13) |
C6 | 0.0546 (15) | 0.0511 (14) | 0.0479 (15) | −0.0027 (13) | 0.0065 (12) | −0.0071 (12) |
C7 | 0.0441 (14) | 0.0543 (16) | 0.0462 (14) | 0.0034 (12) | 0.0069 (11) | 0.0019 (12) |
C8 | 0.095 (2) | 0.0709 (19) | 0.0536 (17) | 0.0165 (17) | 0.0011 (15) | −0.0049 (14) |
C9 | 0.0401 (13) | 0.0500 (15) | 0.0550 (15) | 0.0027 (11) | 0.0094 (11) | 0.0042 (12) |
C10 | 0.0576 (17) | 0.0598 (18) | 0.0613 (16) | 0.0042 (14) | 0.0049 (13) | 0.0087 (14) |
C11 | 0.071 (2) | 0.0591 (19) | 0.092 (2) | 0.0092 (16) | 0.0073 (17) | 0.0181 (17) |
C12 | 0.0651 (19) | 0.0458 (17) | 0.107 (3) | 0.0031 (14) | 0.0068 (17) | −0.0056 (17) |
C13 | 0.0668 (18) | 0.0574 (18) | 0.0794 (19) | −0.0005 (14) | 0.0045 (15) | −0.0138 (16) |
C14 | 0.0608 (17) | 0.0493 (15) | 0.0562 (16) | 0.0036 (13) | 0.0040 (13) | 0.0010 (13) |
Geometric parameters (Å, º) top
O1—N1 | 1.220 (3) | C6—H6 | 0.9300 |
O2—N1 | 1.234 (2) | C7—C9 | 1.480 (3) |
O3—N2 | 1.223 (3) | C7—C8 | 1.500 (3) |
O4—N2 | 1.222 (3) | C8—H8C | 0.9600 |
N1—C2 | 1.450 (3) | C8—H8A | 0.9600 |
N2—C4 | 1.454 (3) | C8—H8B | 0.9600 |
N3—C1 | 1.351 (3) | C9—C14 | 1.389 (3) |
N3—N4 | 1.367 (3) | C9—C10 | 1.392 (3) |
N3—H1 | 0.8600 | C10—C11 | 1.388 (4) |
N4—C7 | 1.286 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.411 (3) | C11—C12 | 1.358 (4) |
C1—C6 | 1.415 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.389 (3) | C12—C13 | 1.376 (4) |
C3—C4 | 1.365 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.376 (3) |
C4—C5 | 1.387 (3) | C13—H13 | 0.9300 |
C5—C6 | 1.360 (3) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | | |
| | | |
O1—N1—O2 | 121.7 (2) | N4—C7—C9 | 115.4 (2) |
O1—N1—C2 | 119.1 (2) | N4—C7—C8 | 123.4 (2) |
O2—N1—C2 | 119.2 (2) | C9—C7—C8 | 121.3 (2) |
O4—N2—O3 | 122.9 (3) | C7—C8—H8C | 109.5 |
O4—N2—C4 | 117.9 (3) | C7—C8—H8A | 109.5 |
O3—N2—C4 | 119.2 (2) | H8C—C8—H8A | 109.5 |
C1—N3—N4 | 120.39 (19) | C7—C8—H8B | 109.5 |
C1—N3—H1 | 119.8 | H8C—C8—H8B | 109.5 |
N4—N3—H1 | 119.8 | H8A—C8—H8B | 109.5 |
C7—N4—N3 | 116.7 (2) | C14—C9—C10 | 117.7 (2) |
N3—C1—C2 | 122.2 (2) | C14—C9—C7 | 120.1 (2) |
N3—C1—C6 | 120.8 (2) | C10—C9—C7 | 122.2 (2) |
C2—C1—C6 | 117.0 (2) | C11—C10—C9 | 120.6 (3) |
C3—C2—C1 | 121.5 (2) | C11—C10—H10 | 119.7 |
C3—C2—N1 | 116.0 (2) | C9—C10—H10 | 119.7 |
C1—C2—N1 | 122.6 (2) | C12—C11—C10 | 120.4 (3) |
C4—C3—C2 | 118.9 (2) | C12—C11—H11 | 119.8 |
C4—C3—H3 | 120.5 | C10—C11—H11 | 119.8 |
C2—C3—H3 | 120.5 | C11—C12—C13 | 120.0 (3) |
C3—C4—C5 | 121.3 (2) | C11—C12—H12 | 120.0 |
C3—C4—N2 | 118.2 (2) | C13—C12—H12 | 120.0 |
C5—C4—N2 | 120.4 (2) | C14—C13—C12 | 120.1 (3) |
C6—C5—C4 | 120.2 (2) | C14—C13—H13 | 119.9 |
C6—C5—H5 | 119.9 | C12—C13—H13 | 119.9 |
C4—C5—H5 | 119.9 | C13—C14—C9 | 121.1 (3) |
C5—C6—C1 | 121.0 (2) | C13—C14—H14 | 119.4 |
C5—C6—H6 | 119.5 | C9—C14—H14 | 119.4 |
C1—C6—H6 | 119.5 | | |
| | | |
C1—N3—N4—C7 | 178.1 (2) | C3—C4—C5—C6 | −0.3 (4) |
N4—N3—C1—C2 | −179.5 (2) | N2—C4—C5—C6 | 179.3 (2) |
N4—N3—C1—C6 | 1.2 (3) | C4—C5—C6—C1 | −0.9 (4) |
N3—C1—C2—C3 | 178.7 (2) | N3—C1—C6—C5 | −178.7 (2) |
C6—C1—C2—C3 | −1.9 (3) | C2—C1—C6—C5 | 1.9 (3) |
N3—C1—C2—N1 | −0.4 (4) | N3—N4—C7—C9 | 178.80 (19) |
C6—C1—C2—N1 | 179.0 (2) | N3—N4—C7—C8 | −0.2 (4) |
O1—N1—C2—C3 | 4.9 (3) | N4—C7—C9—C14 | 4.5 (3) |
O2—N1—C2—C3 | −174.4 (2) | C8—C7—C9—C14 | −176.4 (2) |
O1—N1—C2—C1 | −175.9 (2) | N4—C7—C9—C10 | −174.0 (2) |
O2—N1—C2—C1 | 4.8 (3) | C8—C7—C9—C10 | 5.0 (4) |
C1—C2—C3—C4 | 0.8 (3) | C14—C9—C10—C11 | −0.7 (4) |
N1—C2—C3—C4 | 180.0 (2) | C7—C9—C10—C11 | 177.8 (2) |
C2—C3—C4—C5 | 0.3 (4) | C9—C10—C11—C12 | 0.3 (4) |
C2—C3—C4—N2 | −179.3 (2) | C10—C11—C12—C13 | 0.5 (5) |
O4—N2—C4—C3 | −167.0 (2) | C11—C12—C13—C14 | −0.9 (4) |
O3—N2—C4—C3 | 11.7 (4) | C12—C13—C14—C9 | 0.4 (4) |
O4—N2—C4—C5 | 13.4 (4) | C10—C9—C14—C13 | 0.4 (4) |
O3—N2—C4—C5 | −167.9 (3) | C7—C9—C14—C13 | −178.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1···O2 | 0.86 | 1.97 | 2.607 (3) | 130 |
C10—H10···O2i | 0.93 | 2.60 | 3.450 (3) | 153 |
C14—H14···O4ii | 0.93 | 2.44 | 3.174 (4) | 136 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z−1/2. |
Experimental details
Crystal data |
Chemical formula | C14H12N4O4 |
Mr | 300.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 7.0169 (15), 13.263 (3), 14.8568 (19) |
β (°) | 97.938 (16) |
V (Å3) | 1369.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.42 × 0.32 × 0.22 |
|
Data collection |
Diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2921, 2694, 1212 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.142, 0.96 |
No. of reflections | 2694 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Selected geometric parameters (Å, º) topO1—N1 | 1.220 (3) | C3—C4 | 1.365 (3) |
O2—N1 | 1.234 (2) | C4—C5 | 1.387 (3) |
O3—N2 | 1.223 (3) | C5—C6 | 1.360 (3) |
O4—N2 | 1.222 (3) | C7—C9 | 1.480 (3) |
N1—C2 | 1.450 (3) | C7—C8 | 1.500 (3) |
N2—C4 | 1.454 (3) | C9—C14 | 1.389 (3) |
N3—C1 | 1.351 (3) | C9—C10 | 1.392 (3) |
N3—N4 | 1.367 (3) | C10—C11 | 1.388 (4) |
N4—C7 | 1.286 (3) | C11—C12 | 1.358 (4) |
C1—C2 | 1.411 (3) | C12—C13 | 1.376 (4) |
C1—C6 | 1.415 (3) | C13—C14 | 1.376 (3) |
C2—C3 | 1.389 (3) | | |
| | | |
C1—N3—N4 | 120.39 (19) | N4—C7—C8 | 123.4 (2) |
C7—N4—N3 | 116.7 (2) | C9—C7—C8 | 121.3 (2) |
N4—C7—C9 | 115.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1···O2 | 0.86 | 1.97 | 2.607 (3) | 130 |
C10—H10···O2i | 0.93 | 2.60 | 3.450 (3) | 153 |
C14—H14···O4ii | 0.93 | 2.44 | 3.174 (4) | 136 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z−1/2. |
Some phenylhydrazone derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993). In order to investigate the relationship of the biological activity and the molecular structure, a series of new phenylhydrazone derivatives have been synthesized in this laboratory.
The molecular structure of the title compound, (I), is shown in Fig. 1. The molecule has an approximately planar structure, except for the the N2-nitro group, which is slightly tilted due to intermolcular hydrogen bonding; thus, atoms O3 and O4 deviate from the mean plane of the molecule by 0.284 (3) and −0.199 (3) Å, respectively.
The N3—C1 bond distance of 1.351 (3) Å indicates partial double-bond character. It should be noted that, within the phenyl ring attached to N3, both the C1—C2 bond [1.411 (3) Å] and the C1—C6 bond [1.415 (3) Å] are significantly longer than the average distance of 1.375 (3) Å for the other four C—C bonds; these range from 1.360 (3) to 1.389 (3) Å. A search of the Cambridge Structural Database (Allen & Kennard, 1993) reveals appreciable differences in the C—C distances in free 2,4-dinitrophenylhydrazine (Okabe et al., 1993; Hilgenfeld & Saenger, 1981) and many of its derivatives (Bolte & Dill, 1998; Ohba, 1996; Borwick et al., 1997; Naidu et al., 1996). This is presumably due to the fact that the non-bonding orbital of nitrogen can overlap with the π orbitals of the arene, thus contributing to the iminocyclohexadiene resonance structure.
The N3—N4 bond distance of 1.367 (3) Å is shorter than that found in free 2,4-dinitrophenylhydrazine [1.405 (6) Å; Okabe et al., 1993], while the N4═C7 bond distance of 1.286 (3) Å is longer than the typical N═C bond distance. These values suggest a delocalized double bond in the hydrazone moiety, but not involving C7—C9 [1.480 (3) Å].
The title molecule crystallizes in the E configuration, with the phenyl group (C9–C14) and the N3–2,4-dinitrophenyl group on opposite sides of the C7═N4 double bond; this also means that the methyl group and the N3—H1 bond are on the same side of the N3—N4 bond. The methyl H atoms were located in a difference Fourier map and a torsional parameter was refined for the methyl group. In the present structure, one methyl H atom (H8B) is syn with respect to the C7—C9 bond, the C9—C7—C8—H8B torsion angle being 9.5°. The methyl conformation in this structure is quite different from that calculated by SXGRAPH (Farrugia, 1999) or that reported for p-cyclopropylacetonephenone 2,4-dinitrophenylhydrazone (Drumright et al., 1990). In the former, the H8B···H1 separation is 1.67 Å, whereas in the latter, it is 1.69 Å; in the present structure H8B···H1 is 2.09 Å and thus the methyl conformation better minimizes the steric hindrance between the methyl group and the N3—H1 bond.
An intramolecular hydrogen bond is formed between the N3—H1 group and the adjacent N1-nitro group; this is a common feature of o-nitrophenylhydrazine (Vickery et al., 1985). Intermolecular C—H···O hydrogen bonds exist between the phenyl and nitro groups, as shown in Fig. 1 and Table 2. With the aid of these C—H···O hydrogen bonds, the title molecules are linked to form the supramolecular layered structure. A molecular packing diagram (Fig. 2) shows how neighboring molecules overlap. The separations between adjacent parallel phenyl rings are 3.404 (2) Å (1 − x, −y, −z) and 3.416 (4) Å (2 − x, −y, −z), respectively, indicative of π–π aromatic stacking interactions in the crystal.