4-Dimethyl­amino-N′-(4-nitro­benzyl­idene)benzohydrazide methanol monosolvate

Zhang, X.; Fu, X.; Tan, L.; Wang, C.; Fan, W.

doi:10.1107/S1600536812037063

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2828

https://doi.org/10.1107/S1600536812037063

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4-Dimethylamino-N′-(4-nitrobenzylidene)benzohydrazide methanol monosolvate

Xiyue Zhang,^a ^* Xiaobo Fu,^b Langzhu Tan,^c Chaixia Wang ^b and Weixing Fan ^a

^aChina Animal Heath and Epidemiology Center, Qingdao 266032, People's Republic of China, ^bWorker Hospital of Qingdao Salt Industry, Qingdao 266012, People's Republic of China, and ^cUniversity of Pittsburgh School of Medicine, Pittsburgh, PA 15261, USA
^*Correspondence e-mail: yongxiyue@126.com

(Received 23 August 2012; accepted 27 August 2012; online 1 September 2012)

In the title compound, C₁₆H₁₆N₄O₃·CH₃OH, the aromatic rings form a dihedral angle of 0.4 (2)°. The nitro group is twisted from the attached benzene ring by 7.5 (2)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link alternating hydrazone and methanol molecules into chains in [100]. The crystal packing exhibits π–π interactions between aromatic rings from neighbouring chains [centroid–centroid distances = 3.734 (3) and 3.903 (3) Å].

Related literature

For the biological activity of hydrazone compounds, see: Zhang et al. (2012 ); Cacic et al. (2006 ); Rauf et al. (2008 ); Bedia et al. (2006 ). For similar hydrazone compounds, see: Horkaew et al. (2012 ); Kargar et al. (2012 ); Hu & Liu (2012 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₆N₄O₃·CH₄O
M_r = 344.37
Triclinic, $[P \overline 1]$
a = 6.6621 (12) Å
b = 10.6685 (17) Å
c = 13.3437 (13) Å
α = 72.279 (2)°
β = 83.444 (2)°
γ = 73.984 (2)°
V = 867.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.972, T_max = 0.978
6198 measured reflections
3140 independent reflections
2082 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.208
S = 1.08
3140 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.92	2.733 (2)	170
N2—H2⋯O4ⁱ	0.89 (1)	2.01 (1)	2.889 (2)	170 (2)
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812037063/cv5333sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037063/cv5333Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037063/cv5333Isup3.cml

checkCIF report

Comment top

Hydrazones derived from the condensation reactions of hydrazines with carbonyl-containing compounds have been found to possess many biological activities, such as antibacterial, anticonvulsant, anti-inflamatory, and antitubercular (Zhang et al., 2012; Cacic et al., 2006; Rauf et al., 2008; Bedia et al., 2006). Recently, a number of hydrazones have been prepared and structurally characterized (Horkaew et al., 2012; Kargar et al., 2012; Hu & Liu, 2012). As an extension of work on the structural characterization of hydrazones, the title compound is reported here.

The asymmetric unit of the title compound contains a hydrazone molecule and a methanol molecule of crystallization linked by O—H···O hydrogen bond (Fig. 1). The hydrazone molecule displays a trans conformation with respect to the C=N bond. Two aromatic rings in the hydrazone molecules form a dihedral angle of 0.4 (2)°. The nitro group is twisted from the attached benzene ring at 7.5 (2)°. Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link alternating hydrazone and methanol molecules into chains in [100] (Fig. 2). The crystal packing exhibits π–π interactions between the aromatic ring from the neighbouring chains [centroid-centroid distances 3.734 (3), 3.903 (3) Å].

Related literature top

For the biological activity of hydrazone compounds, see: Zhang et al. (2012); Cacic et al. (2006); Rauf et al. (2008); Bedia et al. (2006). For similar hydrazone compounds, see: Horkaew et al. (2012); Kargar et al. (2012); Hu & Liu (2012). For reference bond lengths, see: Allen et al. (1987).

Experimental top

4-Nitrobenzaldehyde (0.1 mmol, 15.1 mg) and 4-dimethylaminobenzhydrazide (0.1 mmol, 17.9 mg) were stirred in 20 ml methanol at room temperature for 30 min. A large number of small and yellow single crystals were formed by slow evaporation of the methanolic solution containing the compound in air.

Structure description top

For the biological activity of hydrazone compounds, see: Zhang et al. (2012); Cacic et al. (2006); Rauf et al. (2008); Bedia et al. (2006). For similar hydrazone compounds, see: Horkaew et al. (2012); Kargar et al. (2012); Hu & Liu (2012). For reference bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. Hydrogen bond is drawn as a dashed line.
	Fig. 2. A portion of the crystal packing viewed down the b axis. Hydrogen bonds are drawn as dashed lines.

4-Dimethylamino-N'-(4-nitrobenzylidene)benzohydrazide methanol monosolvate top

Crystal data top

C₁₆H₁₆N₄O₃·CH₄O	Z = 2
M_r = 344.37	F(000) = 364
Triclinic, P1	D_x = 1.318 Mg m⁻³
a = 6.6621 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6685 (17) Å	Cell parameters from 2473 reflections
c = 13.3437 (13) Å	θ = 2.5–26.5°
α = 72.279 (2)°	µ = 0.10 mm⁻¹
β = 83.444 (2)°	T = 298 K
γ = 73.984 (2)°	Block, yellow
V = 867.9 (2) Å³	0.30 × 0.27 × 0.23 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3140 independent reflections
Radiation source: fine-focus sealed tube	2082 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 25.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.972, T_max = 0.978	k = −12→12
6198 measured reflections	l = −16→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.1182P)² + 0.1132P] where P = (F_o² + 2F_c²)/3
3140 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₆H₁₆N₄O₃·CH₄O	γ = 73.984 (2)°
M_r = 344.37	V = 867.9 (2) Å³
Triclinic, P1	Z = 2
a = 6.6621 (12) Å	Mo Kα radiation
b = 10.6685 (17) Å	µ = 0.10 mm⁻¹
c = 13.3437 (13) Å	T = 298 K
α = 72.279 (2)°	0.30 × 0.27 × 0.23 mm
β = 83.444 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3140 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2082 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.978	R_int = 0.035
6198 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.32 e Å⁻³
3140 reflections	Δρ_min = −0.40 e Å⁻³
233 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
N1	0.0844 (3)	0.62271 (17)	0.39221 (13)	0.0471 (5)
N2	0.0240 (3)	0.56468 (18)	0.32624 (14)	0.0478 (5)
N3	0.1415 (4)	0.9440 (2)	0.71802 (16)	0.0655 (6)
N4	−0.0400 (4)	0.2426 (2)	−0.00213 (16)	0.0715 (6)
O1	0.3228 (3)	0.9304 (2)	0.7318 (2)	0.1055 (8)
O2	−0.0001 (4)	1.0126 (2)	0.75895 (17)	0.0929 (7)
O3	0.3593 (2)	0.47225 (17)	0.29021 (14)	0.0672 (5)
O4	0.5727 (2)	0.63544 (19)	0.33104 (18)	0.0796 (6)
H4	0.4999	0.5874	0.3254	0.119*
C1	−0.0040 (3)	0.7521 (2)	0.51346 (15)	0.0427 (5)
C2	0.2010 (3)	0.7245 (2)	0.54349 (16)	0.0484 (5)
H2A	0.3067	0.6636	0.5177	0.058*
C3	0.2480 (3)	0.7863 (2)	0.61062 (17)	0.0516 (6)
H3	0.3848	0.7679	0.6307	0.062*
C4	0.0892 (3)	0.8763 (2)	0.64797 (16)	0.0481 (5)
C5	−0.1143 (3)	0.9036 (2)	0.62214 (17)	0.0520 (6)
H5	−0.2194	0.9628	0.6498	0.062*
C6	−0.1598 (3)	0.8413 (2)	0.55424 (17)	0.0508 (5)
H6	−0.2973	0.8594	0.5354	0.061*
C7	−0.0577 (3)	0.6877 (2)	0.44223 (17)	0.0486 (5)
H7	−0.1971	0.6943	0.4334	0.058*
C8	0.1735 (3)	0.4890 (2)	0.27631 (17)	0.0458 (5)
C9	0.1067 (3)	0.4274 (2)	0.20565 (16)	0.0436 (5)
C10	0.2582 (3)	0.3367 (2)	0.16454 (18)	0.0561 (6)
H10	0.3963	0.3175	0.1828	0.067*
C11	0.2113 (4)	0.2743 (3)	0.09784 (19)	0.0611 (6)
H11	0.3172	0.2125	0.0730	0.073*
C12	0.0067 (4)	0.3021 (2)	0.06654 (17)	0.0537 (6)
C13	−0.1459 (3)	0.3920 (2)	0.10855 (17)	0.0547 (6)
H13	−0.2842	0.4112	0.0904	0.066*
C14	−0.0978 (3)	0.4533 (2)	0.17627 (17)	0.0495 (5)
H14	−0.2038	0.5131	0.2029	0.059*
C15	−0.2519 (5)	0.2624 (4)	−0.0273 (2)	0.0884 (9)
H15A	−0.3265	0.2215	0.0343	0.133*
H15B	−0.2541	0.2210	−0.0816	0.133*
H15C	−0.3171	0.3581	−0.0515	0.133*
C16	0.1216 (6)	0.1550 (4)	−0.0473 (3)	0.1070 (12)
H16A	0.2272	0.2015	−0.0802	0.161*
H16B	0.0640	0.1302	−0.0991	0.161*
H16C	0.1825	0.0745	0.0068	0.161*
C17	0.4766 (4)	0.7717 (3)	0.2827 (2)	0.0819 (8)
H17A	0.3486	0.7993	0.3205	0.123*
H17B	0.4468	0.7823	0.2114	0.123*
H17C	0.5681	0.8271	0.2830	0.123*
H2	−0.1140 (17)	0.579 (3)	0.324 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0436 (9)	0.0531 (10)	0.0547 (10)	−0.0173 (8)	−0.0043 (8)	−0.0244 (8)
N2	0.0375 (9)	0.0586 (11)	0.0595 (11)	−0.0156 (8)	−0.0030 (8)	−0.0311 (9)
N3	0.0835 (15)	0.0537 (12)	0.0673 (13)	−0.0147 (11)	−0.0210 (11)	−0.0247 (10)
N4	0.0817 (15)	0.0936 (16)	0.0658 (13)	−0.0425 (13)	0.0073 (11)	−0.0464 (12)
O1	0.0872 (15)	0.1166 (18)	0.146 (2)	−0.0217 (13)	−0.0391 (14)	−0.0764 (15)
O2	0.1084 (16)	0.0876 (14)	0.0976 (15)	−0.0057 (12)	−0.0188 (12)	−0.0597 (12)
O3	0.0373 (8)	0.0834 (12)	0.1006 (13)	−0.0109 (8)	−0.0093 (8)	−0.0561 (10)
O4	0.0382 (9)	0.0841 (13)	0.1399 (17)	−0.0125 (8)	−0.0084 (9)	−0.0664 (12)
C1	0.0416 (11)	0.0459 (11)	0.0455 (11)	−0.0149 (9)	−0.0015 (8)	−0.0166 (9)
C2	0.0425 (11)	0.0522 (12)	0.0542 (12)	−0.0093 (9)	−0.0034 (9)	−0.0223 (10)
C3	0.0445 (12)	0.0567 (13)	0.0575 (13)	−0.0133 (10)	−0.0108 (10)	−0.0183 (10)
C4	0.0586 (13)	0.0435 (11)	0.0468 (12)	−0.0157 (10)	−0.0077 (10)	−0.0150 (9)
C5	0.0523 (12)	0.0505 (12)	0.0554 (13)	−0.0082 (10)	0.0002 (10)	−0.0236 (10)
C6	0.0397 (11)	0.0573 (13)	0.0600 (13)	−0.0123 (10)	−0.0014 (9)	−0.0236 (10)
C7	0.0395 (11)	0.0558 (13)	0.0583 (13)	−0.0152 (10)	−0.0024 (9)	−0.0243 (10)
C8	0.0375 (11)	0.0487 (12)	0.0576 (13)	−0.0132 (9)	−0.0034 (9)	−0.0217 (10)
C9	0.0390 (10)	0.0490 (12)	0.0490 (11)	−0.0161 (9)	−0.0002 (8)	−0.0190 (9)
C10	0.0405 (11)	0.0689 (15)	0.0705 (15)	−0.0184 (10)	0.0038 (10)	−0.0346 (12)
C11	0.0551 (13)	0.0725 (16)	0.0718 (15)	−0.0232 (12)	0.0103 (11)	−0.0419 (13)
C12	0.0632 (14)	0.0644 (14)	0.0477 (12)	−0.0332 (12)	0.0039 (10)	−0.0232 (10)
C13	0.0489 (12)	0.0664 (14)	0.0578 (13)	−0.0211 (11)	−0.0083 (10)	−0.0223 (11)
C14	0.0416 (11)	0.0569 (13)	0.0572 (13)	−0.0147 (10)	−0.0025 (9)	−0.0245 (10)
C15	0.097 (2)	0.120 (2)	0.0789 (19)	−0.0550 (19)	−0.0136 (16)	−0.0449 (17)
C16	0.112 (3)	0.148 (3)	0.112 (3)	−0.066 (2)	0.034 (2)	−0.095 (3)
C17	0.0672 (16)	0.101 (2)	0.085 (2)	−0.0297 (16)	−0.0022 (14)	−0.0310 (17)

Geometric parameters (Å, º) top

N1—C7	1.264 (3)	C6—H6	0.9300
N1—N2	1.368 (2)	C7—H7	0.9300
N2—C8	1.349 (3)	C8—C9	1.468 (3)
N2—H2	0.892 (10)	C9—C10	1.383 (3)
N3—O1	1.205 (3)	C9—C14	1.390 (3)
N3—O2	1.212 (3)	C10—C11	1.368 (3)
N3—C4	1.464 (3)	C10—H10	0.9300
N4—C12	1.367 (3)	C11—C12	1.398 (3)
N4—C16	1.427 (4)	C11—H11	0.9300
N4—C15	1.432 (3)	C12—C13	1.388 (3)
O3—C8	1.228 (2)	C13—C14	1.374 (3)
O4—C17	1.396 (3)	C13—H13	0.9300
O4—H4	0.8200	C14—H14	0.9300
C1—C6	1.386 (3)	C15—H15A	0.9600
C1—C2	1.394 (3)	C15—H15B	0.9600
C1—C7	1.454 (3)	C15—H15C	0.9600
C2—C3	1.368 (3)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.378 (3)	C16—H16C	0.9600
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.367 (3)	C17—H17B	0.9600
C5—C6	1.376 (3)	C17—H17C	0.9600
C5—H5	0.9300

C7—N1—N2	117.48 (17)	C10—C9—C8	117.77 (18)
C8—N2—N1	118.39 (17)	C14—C9—C8	125.07 (18)
C8—N2—H2	126.9 (17)	C11—C10—C9	122.1 (2)
N1—N2—H2	114.6 (17)	C11—C10—H10	119.0
O1—N3—O2	122.8 (2)	C9—C10—H10	119.0
O1—N3—C4	118.8 (2)	C10—C11—C12	120.9 (2)
O2—N3—C4	118.4 (2)	C10—C11—H11	119.5
C12—N4—C16	120.4 (2)	C12—C11—H11	119.5
C12—N4—C15	121.0 (2)	N4—C12—C13	121.8 (2)
C16—N4—C15	118.5 (2)	N4—C12—C11	121.1 (2)
C17—O4—H4	109.5	C13—C12—C11	117.08 (19)
C6—C1—C2	118.84 (19)	C14—C13—C12	121.61 (19)
C6—C1—C7	119.61 (19)	C14—C13—H13	119.2
C2—C1—C7	121.54 (18)	C12—C13—H13	119.2
C3—C2—C1	120.56 (19)	C13—C14—C9	121.15 (19)
C3—C2—H2A	119.7	C13—C14—H14	119.4
C1—C2—H2A	119.7	C9—C14—H14	119.4
C2—C3—C4	118.83 (19)	N4—C15—H15A	109.5
C2—C3—H3	120.6	N4—C15—H15B	109.5
C4—C3—H3	120.6	H15A—C15—H15B	109.5
C5—C4—C3	122.28 (19)	N4—C15—H15C	109.5
C5—C4—N3	119.25 (19)	H15A—C15—H15C	109.5
C3—C4—N3	118.5 (2)	H15B—C15—H15C	109.5
C4—C5—C6	118.42 (19)	N4—C16—H16A	109.5
C4—C5—H5	120.8	N4—C16—H16B	109.5
C6—C5—H5	120.8	H16A—C16—H16B	109.5
C5—C6—C1	121.0 (2)	N4—C16—H16C	109.5
C5—C6—H6	119.5	H16A—C16—H16C	109.5
C1—C6—H6	119.5	H16B—C16—H16C	109.5
N1—C7—C1	120.24 (19)	O4—C17—H17A	109.5
N1—C7—H7	119.9	O4—C17—H17B	109.5
C1—C7—H7	119.9	H17A—C17—H17B	109.5
O3—C8—N2	120.71 (18)	O4—C17—H17C	109.5
O3—C8—C9	121.40 (18)	H17A—C17—H17C	109.5
N2—C8—C9	117.89 (17)	H17B—C17—H17C	109.5
C10—C9—C14	117.15 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.92	2.733 (2)	170
N2—H2···O4ⁱ	0.89 (1)	2.01 (1)	2.889 (2)	170 (2)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₄O₃·CH₄O
M_r	344.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.6621 (12), 10.6685 (17), 13.3437 (13)
α, β, γ (°)	72.279 (2), 83.444 (2), 73.984 (2)
V (Å³)	867.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.27 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	6198, 3140, 2082
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.208, 1.08
No. of reflections	3140
No. of parameters	233
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.40

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.92	2.733 (2)	169.8
N2—H2···O4ⁱ	0.892 (10)	2.006 (11)	2.889 (2)	170 (2)

Symmetry code: (i) x−1, y, z.

References

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