4-Dimethyl-amino-N'-(4-nitro-benzyl-idene)benzohydrazide methanol monosolvate.

In the title compound, C(16)H(16)N(4)O(3)·CH(3)OH, 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 mol-ecules into chains in [100]. The crystal packing exhibits π-π inter-actions 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 = 344.37

Triclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.208

S = 1.08

3140 reflections

233 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.40 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037063/cv5333sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037063/cv5333Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037063/cv5333Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16N4O3·CH4O	Z = 2
Mr = 344.37	F(000) = 364
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1182P)2 + 0.1132P] where P = (Fo2 + 2Fc2)/3
3140 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .