N'-(3,5-Dichloro-2-hy-droxy-benzyl-idene)-4-(dimethyl-amino)-benzohydrazide methanol monosolvate.

The title compound, C(16)H(15)Cl(2)N(3)O(2)·CH(3)OH, a Schiff base molecule, is prepared by the reaction of 3,5-dichloro-salicyl-aldehyde with 4-dimethyl-amino-benzohydrazide in methanol. The Schiff base mol-ecule is approximately planar, with a mean deviation from the least-squares plane defined by the non-H atoms of 0.0452 (3) Å, and with a dihedral angle between the benzene rings of 4.2 (3)°. This planarity is assisted by the formation of an intra-molecular O-H⋯N hydrogen bond. In the crystal, adjacent Schiff base mol-ecules are linked by two methanol mol-ecules through N-H⋯O and O-H⋯O hydrogen bonds, forming dimers.

Related literature

For the preparation of Schiff base compounds by the condensation reaction between aldehydes with organic primary amines, see: Miura et al. (2009 ▶); Zhao et al. (2010 ▶); Karadağ et al. (2011) ▶; Bingöl Alpaslan et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H15Cl2N3O2·CH4O

M = 384.25

Monoclinic,

a = 7.6498 (15) Å

b = 14.338 (3) Å

c = 16.884 (2) Å

β = 103.076 (2)°

V = 1803.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 298 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.952, T max = 0.963

8311 measured reflections

3238 independent reflections

1790 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.180

S = 1.03

3238 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010148/qm2057sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010148/qm2057Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010148/qm2057Isup3.cml

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

C16H15Cl2N3O2·CH4O	F(000) = 800
Mr = 384.25	Dx = 1.415 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.6498 (15) Å	Cell parameters from 2546 reflections
b = 14.338 (3) Å	θ = 2.5–28.3°
c = 16.884 (2) Å	µ = 0.38 mm−1
β = 103.076 (2)°	T = 298 K
V = 1803.8 (5) Å3	Block, colorless
Z = 4	0.13 × 0.12 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3238 independent reflections
Radiation source: fine-focus sealed tube	1790 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.952, Tmax = 0.963	k = −16→17
8311 measured reflections	l = −13→20

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.8315P] where P = (Fo2 + 2Fc2)/3
3238 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
Cl1	0.4325 (2)	0.29209 (10)	0.15198 (9)	0.0674 (5)
Cl2	0.4175 (2)	0.65692 (11)	0.07222 (9)	0.0719 (5)
N1	0.2957 (5)	0.4874 (3)	0.4015 (2)	0.0450 (10)
N2	0.2686 (5)	0.5167 (3)	0.4749 (2)	0.0431 (10)
H2	0.2702	0.5751	0.4864	0.052*
N3	0.1064 (6)	0.5808 (3)	0.8296 (2)	0.0490 (11)
O1	0.3448 (5)	0.3581 (2)	0.3007 (2)	0.0564 (10)
H1	0.3013	0.3780	0.3376	0.085*
O2	0.2453 (5)	0.3677 (2)	0.5161 (2)	0.0530 (10)
O3	0.5727 (5)	0.3035 (2)	0.4941 (2)	0.0608 (10)
H3	0.4685	0.3145	0.4960	0.091*
C1	0.3425 (6)	0.5229 (3)	0.2711 (3)	0.0394 (12)
C2	0.3621 (6)	0.4282 (3)	0.2505 (3)	0.0420 (12)
C3	0.4009 (6)	0.4078 (4)	0.1756 (3)	0.0483 (13)
C4	0.4178 (6)	0.4767 (4)	0.1208 (3)	0.0463 (13)
H4	0.4441	0.4616	0.0712	0.056*
C5	0.3950 (6)	0.5682 (4)	0.1411 (3)	0.0481 (13)
C6	0.3577 (6)	0.5909 (4)	0.2145 (3)	0.0474 (13)
H6	0.3422	0.6532	0.2266	0.057*
C7	0.3097 (6)	0.5495 (3)	0.3482 (3)	0.0407 (12)
H7	0.2984	0.6123	0.3599	0.049*
C8	0.2386 (6)	0.4510 (4)	0.5302 (3)	0.0388 (12)
C9	0.1976 (6)	0.4892 (3)	0.6054 (3)	0.0363 (11)
C10	0.1902 (6)	0.4268 (3)	0.6673 (3)	0.0408 (12)
H10	0.2087	0.3637	0.6592	0.049*
C11	0.1562 (6)	0.4551 (3)	0.7403 (3)	0.0436 (12)
H11	0.1497	0.4109	0.7799	0.052*
C12	0.1311 (6)	0.5505 (3)	0.7556 (3)	0.0358 (11)
C13	0.1359 (6)	0.6129 (3)	0.6922 (3)	0.0455 (12)
H13	0.1173	0.6761	0.6996	0.055*
C14	0.1672 (6)	0.5830 (3)	0.6193 (3)	0.0427 (12)
H14	0.1681	0.6263	0.5784	0.051*
C15	0.0961 (8)	0.5155 (4)	0.8937 (3)	0.0577 (15)
H15A	0.0012	0.4716	0.8743	0.087*
H15B	0.0723	0.5487	0.9395	0.087*
H15C	0.2080	0.4827	0.9098	0.087*
C16	0.0752 (7)	0.6783 (4)	0.8461 (3)	0.0591 (15)
H16A	0.1787	0.7145	0.8425	0.089*
H16B	0.0538	0.6841	0.8997	0.089*
H16C	−0.0274	0.7007	0.8069	0.089*
C17	0.5794 (7)	0.2197 (4)	0.4506 (3)	0.0619 (16)
H17A	0.7002	0.1964	0.4626	0.093*
H17B	0.5411	0.2315	0.3934	0.093*
H17C	0.5016	0.1743	0.4665	0.093*

	U11	U22	U33	U12	U13	U23
Cl1	0.0718 (10)	0.0608 (9)	0.0729 (10)	0.0044 (7)	0.0235 (8)	−0.0241 (8)
Cl2	0.0840 (11)	0.0797 (11)	0.0536 (9)	−0.0156 (9)	0.0192 (8)	0.0149 (8)
N1	0.047 (3)	0.048 (3)	0.040 (3)	0.000 (2)	0.011 (2)	−0.009 (2)
N2	0.057 (3)	0.039 (2)	0.033 (2)	−0.002 (2)	0.010 (2)	−0.0098 (19)
N3	0.071 (3)	0.037 (2)	0.046 (3)	−0.001 (2)	0.026 (2)	0.000 (2)
O1	0.078 (3)	0.045 (2)	0.048 (2)	0.0047 (19)	0.018 (2)	0.0026 (18)
O2	0.074 (2)	0.035 (2)	0.055 (2)	0.0019 (17)	0.0234 (19)	−0.0095 (17)
O3	0.069 (2)	0.041 (2)	0.077 (3)	−0.0039 (19)	0.025 (2)	−0.0124 (19)
C1	0.035 (3)	0.046 (3)	0.034 (3)	−0.002 (2)	0.001 (2)	−0.005 (2)
C2	0.043 (3)	0.049 (3)	0.031 (3)	−0.002 (2)	0.002 (2)	0.001 (2)
C3	0.042 (3)	0.058 (3)	0.047 (3)	−0.002 (2)	0.014 (2)	−0.013 (3)
C4	0.037 (3)	0.070 (4)	0.032 (3)	−0.002 (2)	0.007 (2)	0.000 (3)
C5	0.044 (3)	0.062 (4)	0.036 (3)	−0.016 (3)	0.004 (2)	0.006 (3)
C6	0.050 (3)	0.044 (3)	0.046 (3)	−0.008 (2)	0.005 (2)	0.000 (3)
C7	0.042 (3)	0.040 (3)	0.039 (3)	0.002 (2)	0.007 (2)	−0.004 (2)
C8	0.029 (3)	0.050 (3)	0.037 (3)	−0.003 (2)	0.008 (2)	0.000 (3)
C9	0.036 (3)	0.038 (3)	0.038 (3)	−0.002 (2)	0.015 (2)	−0.003 (2)
C10	0.040 (3)	0.032 (3)	0.053 (3)	0.002 (2)	0.015 (2)	−0.002 (2)
C11	0.047 (3)	0.043 (3)	0.043 (3)	0.005 (2)	0.016 (2)	0.008 (2)
C12	0.036 (3)	0.036 (3)	0.037 (3)	−0.005 (2)	0.013 (2)	−0.005 (2)
C13	0.055 (3)	0.033 (3)	0.052 (3)	0.000 (2)	0.020 (3)	−0.003 (3)
C14	0.058 (3)	0.032 (3)	0.043 (3)	0.004 (2)	0.021 (2)	0.005 (2)
C15	0.070 (4)	0.063 (4)	0.042 (3)	0.003 (3)	0.015 (3)	−0.001 (3)
C16	0.068 (4)	0.054 (3)	0.062 (4)	0.001 (3)	0.030 (3)	−0.011 (3)
C17	0.074 (4)	0.053 (4)	0.063 (4)	0.009 (3)	0.024 (3)	−0.009 (3)

Cl1—C3	1.736 (5)	C6—H6	0.9300
Cl2—C5	1.758 (5)	C7—H7	0.9300
N1—C7	1.288 (6)	C8—C9	1.480 (6)
N1—N2	1.367 (5)	C9—C10	1.387 (6)
N2—C8	1.381 (6)	C9—C14	1.394 (6)
N2—H2	0.8600	C10—C11	1.378 (6)
N3—C12	1.374 (6)	C10—H10	0.9300
N3—C15	1.447 (6)	C11—C12	1.414 (6)
N3—C16	1.456 (6)	C11—H11	0.9300
O1—C2	1.342 (5)	C12—C13	1.402 (6)
O1—H1	0.8200	C13—C14	1.374 (6)
O2—C8	1.222 (5)	C13—H13	0.9300
O3—C17	1.415 (6)	C14—H14	0.9300
O3—H3	0.8200	C15—H15A	0.9600
C1—C6	1.388 (6)	C15—H15B	0.9600
C1—C2	1.417 (6)	C15—H15C	0.9600
C1—C7	1.433 (6)	C16—H16A	0.9600
C2—C3	1.393 (6)	C16—H16B	0.9600
C3—C4	1.379 (7)	C16—H16C	0.9600
C4—C5	1.378 (7)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.372 (7)	C17—H17C	0.9600
C7—N1—N2	118.3 (4)	C14—C9—C8	125.3 (4)
N1—N2—C8	119.1 (4)	C11—C10—C9	122.2 (4)
N1—N2—H2	120.5	C11—C10—H10	118.9
C8—N2—H2	120.5	C9—C10—H10	118.9
C12—N3—C15	121.1 (4)	C10—C11—C12	120.6 (4)
C12—N3—C16	122.6 (4)	C10—C11—H11	119.7
C15—N3—C16	116.1 (4)	C12—C11—H11	119.7
C2—O1—H1	109.5	N3—C12—C13	121.7 (4)
C17—O3—H3	109.5	N3—C12—C11	121.6 (4)
C6—C1—C2	118.3 (4)	C13—C12—C11	116.7 (4)
C6—C1—C7	119.8 (5)	C14—C13—C12	121.6 (4)
C2—C1—C7	121.9 (5)	C14—C13—H13	119.2
O1—C2—C3	119.2 (5)	C12—C13—H13	119.2
O1—C2—C1	122.1 (4)	C13—C14—C9	121.5 (5)
C3—C2—C1	118.7 (5)	C13—C14—H14	119.3
C4—C3—C2	122.0 (5)	C9—C14—H14	119.3
C4—C3—Cl1	119.4 (4)	N3—C15—H15A	109.5
C2—C3—Cl1	118.6 (4)	N3—C15—H15B	109.5
C5—C4—C3	118.6 (5)	H15A—C15—H15B	109.5
C5—C4—H4	120.7	N3—C15—H15C	109.5
C3—C4—H4	120.7	H15A—C15—H15C	109.5
C6—C5—C4	120.9 (5)	H15B—C15—H15C	109.5
C6—C5—Cl2	119.9 (4)	N3—C16—H16A	109.5
C4—C5—Cl2	119.2 (4)	N3—C16—H16B	109.5
C5—C6—C1	121.5 (5)	H16A—C16—H16B	109.5
C5—C6—H6	119.3	N3—C16—H16C	109.5
C1—C6—H6	119.3	H16A—C16—H16C	109.5
N1—C7—C1	120.7 (4)	H16B—C16—H16C	109.5
N1—C7—H7	119.7	O3—C17—H17A	109.5
C1—C7—H7	119.7	O3—C17—H17B	109.5
O2—C8—N2	120.9 (4)	H17A—C17—H17B	109.5
O2—C8—C9	123.7 (4)	O3—C17—H17C	109.5
N2—C8—C9	115.4 (4)	H17A—C17—H17C	109.5
C10—C9—C14	117.3 (4)	H17B—C17—H17C	109.5
C10—C9—C8	117.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.86	2.10	2.848 (5)	145
O1—H1···N1	0.82	1.91	2.600 (5)	141
O3—H3···O2	0.82	1.97	2.771 (5)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.86	2.10	2.848 (5)	145
O1—H1⋯N1	0.82	1.91	2.600 (5)	141
O3—H3⋯O2	0.82	1.97	2.771 (5)	166

Symmetry code: (i) .