(E)-4-Hy-droxy-N'-(2-hy-droxy-5-iodo-benzyl-idene)benzohydrazide methanol monosolvate.

In the title compound, C(14)H(11)IN(2)O(3)·CH(4)O, the dihedral angle between the benzene rings is 33.2 (3)°. The mol-ecule displays trans and anti conformations about the C=N and N-N bonds, respectively. There is an intra-molecular O-H⋯N(azomethine) hydrogen bond. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds consolidate mol-ecules into a three-dimensional architecture.

Related literature

For the structures of related carbohydrazides, see: Monfared et al. (2010a ▶); Bikas et al. (2010a ▶,b ▶, 2012a ▶,b ▶). For catalytic applications of aroylhydrazones, see: Monfared et al. (2010b ▶).

Experimental

Crystal data

C14H11IN2O3·CH4O

M = 414.19

Monoclinic,

a = 10.1077 (7) Å

b = 12.5703 (11) Å

c = 13.1586 (17) Å

β = 102.886 (10)°

V = 1629.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.98 mm−1

T = 293 K

0.3 × 0.3 × 0.3 mm

Data collection

Agilent SuperNova (Single source at offset), Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.864, T max = 1.000

3370 measured reflections

2094 independent reflections

1981 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.04

2094 reflections

201 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 419 Friedel pairs

Flack parameter: −0.01 (3)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034848/tk5140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034848/tk5140Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034848/tk5140Isup3.cml

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

C14H11IN2O3·CH4O	F(000) = 816
Mr = 414.19	Dx = 1.688 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1140 reflections
a = 10.1077 (7) Å	θ = 3.3–32.3°
b = 12.5703 (11) Å	µ = 1.98 mm−1
c = 13.1586 (17) Å	T = 293 K
β = 102.886 (10)°	Block, colourless
V = 1629.8 (3) Å3	0.3 × 0.3 × 0.3 mm
Z = 4

Agilent SuperNova (Single source at offset), Eos diffractometer	2094 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1981 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 16.0454 pixels mm-1	θmax = 26.4°, θmin = 3.3°
ω scans	h = −12→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→15
Tmin = 0.864, Tmax = 1.000	l = −16→14
3370 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2094 reflections	Δρmax = 0.32 e Å−3
201 parameters	Δρmin = −0.56 e Å−3
2 restraints	Absolute structure: Flack (1983), 419 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (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
I1	0.71478 (4)	0.35952 (3)	0.30013 (4)	0.05205 (16)
O1	0.3254 (6)	0.5311 (5)	0.5685 (4)	0.0672 (17)
H1	0.2521	0.5492	0.5321	0.101*
O2	−0.0512 (5)	0.6112 (4)	0.4916 (3)	0.0450 (11)
O3	−0.5681 (5)	0.7936 (4)	0.1732 (3)	0.0548 (13)
H3	−0.5634	0.8156	0.1155	0.082*
O4	0.0029 (7)	0.5759 (4)	0.1189 (4)	0.0613 (15)
H4	−0.0129	0.5213	0.0842	0.092*
N1	0.1430 (6)	0.5574 (5)	0.3960 (4)	0.0412 (12)
N2	0.0194 (5)	0.5934 (4)	0.3409 (4)	0.0379 (11)
H2	0.0008	0.5958	0.2739	0.045*
C1	0.4061 (7)	0.4922 (6)	0.5066 (5)	0.0469 (16)
C2	0.5354 (8)	0.4584 (7)	0.5544 (5)	0.0553 (19)
H2A	0.5635	0.4611	0.6266	0.066*
C3	0.6226 (7)	0.4209 (6)	0.4960 (5)	0.0472 (16)
H3A	0.7102	0.4002	0.5285	0.057*
C4	0.5793 (6)	0.4142 (5)	0.3886 (4)	0.0376 (13)
C5	0.4500 (6)	0.4478 (5)	0.3393 (4)	0.0369 (13)
H5	0.4225	0.4441	0.2671	0.044*
C6	0.3614 (6)	0.4868 (5)	0.3973 (4)	0.0359 (13)
C7	0.2277 (6)	0.5220 (5)	0.3436 (5)	0.0395 (14)
H7	0.2027	0.5190	0.2712	0.047*
C8	−0.0721 (7)	0.6251 (4)	0.3958 (4)	0.0336 (13)
C9	−0.1990 (6)	0.6748 (5)	0.3356 (4)	0.0318 (12)
C10	−0.3134 (7)	0.6734 (6)	0.3778 (5)	0.0407 (14)
H10	−0.3078	0.6452	0.4439	0.049*
C11	−0.4344 (7)	0.7135 (6)	0.3224 (5)	0.0426 (15)
H11	−0.5112	0.7094	0.3502	0.051*
C12	−0.4438 (6)	0.7604 (5)	0.2252 (4)	0.0371 (13)
C13	−0.3289 (6)	0.7659 (5)	0.1848 (4)	0.0374 (13)
H13	−0.3338	0.7982	0.1204	0.045*
C14	−0.2068 (7)	0.7242 (5)	0.2388 (5)	0.0369 (14)
H14	−0.1301	0.7288	0.2110	0.044*
C15	0.0531 (14)	0.6548 (7)	0.0605 (7)	0.075 (3)
H15A	−0.0125	0.7109	0.0429	0.112*
H15B	0.0696	0.6238	−0.0022	0.112*
H15C	0.1363	0.6833	0.1013	0.112*

	U11	U22	U33	U12	U13	U23
I1	0.0380 (2)	0.0592 (3)	0.0620 (3)	0.0113 (3)	0.01773 (16)	−0.0025 (2)
O1	0.054 (3)	0.108 (5)	0.039 (2)	0.030 (4)	0.010 (2)	−0.005 (2)
O2	0.043 (3)	0.057 (3)	0.035 (2)	0.009 (2)	0.0088 (19)	0.0027 (18)
O3	0.036 (3)	0.080 (4)	0.052 (3)	0.020 (3)	0.016 (2)	0.019 (2)
O4	0.083 (4)	0.062 (3)	0.040 (2)	−0.015 (3)	0.015 (2)	−0.007 (2)
N1	0.031 (3)	0.053 (3)	0.038 (2)	0.006 (3)	0.005 (2)	0.002 (2)
N2	0.030 (3)	0.048 (3)	0.035 (2)	0.009 (3)	0.006 (2)	−0.002 (2)
C1	0.041 (4)	0.060 (4)	0.040 (3)	0.011 (3)	0.007 (3)	0.004 (3)
C2	0.042 (4)	0.079 (5)	0.041 (3)	0.015 (4)	0.000 (3)	0.005 (3)
C3	0.032 (3)	0.059 (4)	0.048 (3)	0.008 (3)	0.003 (3)	0.004 (3)
C4	0.032 (3)	0.038 (3)	0.045 (3)	0.002 (3)	0.012 (3)	0.000 (2)
C5	0.034 (3)	0.043 (3)	0.032 (3)	0.003 (3)	0.005 (2)	−0.002 (2)
C6	0.030 (3)	0.039 (3)	0.036 (3)	0.003 (3)	0.004 (2)	−0.001 (2)
C7	0.032 (3)	0.053 (4)	0.034 (3)	0.002 (3)	0.007 (2)	−0.001 (2)
C8	0.031 (3)	0.034 (3)	0.035 (3)	0.001 (2)	0.006 (2)	−0.001 (2)
C9	0.032 (3)	0.031 (3)	0.032 (3)	0.005 (2)	0.007 (2)	−0.003 (2)
C10	0.040 (4)	0.051 (4)	0.035 (3)	0.004 (3)	0.016 (3)	0.005 (3)
C11	0.035 (3)	0.057 (4)	0.041 (3)	0.012 (3)	0.019 (3)	0.010 (3)
C12	0.030 (3)	0.041 (3)	0.043 (3)	0.009 (3)	0.012 (2)	0.004 (2)
C13	0.034 (3)	0.044 (3)	0.036 (3)	0.004 (3)	0.012 (2)	0.009 (2)
C14	0.032 (3)	0.047 (4)	0.034 (3)	−0.001 (3)	0.012 (3)	0.001 (2)
C15	0.099 (9)	0.066 (5)	0.061 (5)	−0.003 (5)	0.021 (5)	−0.003 (4)

I1—C4	2.101 (6)	C5—C6	1.389 (9)
O1—C1	1.365 (9)	C5—H5	0.9300
O1—H1	0.8200	C6—C7	1.447 (8)
O2—C8	1.243 (7)	C7—H7	0.9300
O3—C12	1.355 (7)	C8—C9	1.486 (8)
O3—H3	0.8200	C9—C10	1.390 (9)
O4—C15	1.416 (12)	C9—C14	1.403 (8)
O4—H4	0.8200	C10—C11	1.373 (9)
N1—C7	1.292 (9)	C10—H10	0.9300
N1—N2	1.374 (7)	C11—C12	1.392 (9)
N2—C8	1.355 (8)	C11—H11	0.9300
N2—H2	0.8600	C12—C13	1.383 (9)
C1—C2	1.385 (10)	C13—C14	1.383 (9)
C1—C6	1.409 (8)	C13—H13	0.9300
C2—C3	1.375 (10)	C14—H14	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.387 (9)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.388 (8)
C1—O1—H1	109.5	O2—C8—N2	121.2 (6)
C12—O3—H3	109.5	O2—C8—C9	122.1 (6)
C15—O4—H4	109.5	N2—C8—C9	116.7 (5)
C7—N1—N2	117.7 (5)	C10—C9—C14	119.0 (6)
C8—N2—N1	117.7 (5)	C10—C9—C8	118.5 (5)
C8—N2—H2	121.2	C14—C9—C8	122.5 (6)
N1—N2—H2	121.2	C11—C10—C9	120.4 (6)
O1—C1—C2	117.9 (6)	C11—C10—H10	119.8
O1—C1—C6	121.9 (6)	C9—C10—H10	119.8
C2—C1—C6	120.3 (7)	C10—C11—C12	120.9 (6)
C3—C2—C1	120.6 (6)	C10—C11—H11	119.6
C3—C2—H2A	119.7	C12—C11—H11	119.6
C1—C2—H2A	119.7	O3—C12—C13	123.6 (5)
C2—C3—C4	119.6 (6)	O3—C12—C11	117.3 (6)
C2—C3—H3A	120.2	C13—C12—C11	118.9 (6)
C4—C3—H3A	120.2	C12—C13—C14	120.9 (5)
C3—C4—C5	120.5 (6)	C12—C13—H13	119.6
C3—C4—I1	119.2 (5)	C14—C13—H13	119.6
C5—C4—I1	120.2 (4)	C13—C14—C9	119.9 (6)
C4—C5—C6	120.4 (5)	C13—C14—H14	120.1
C4—C5—H5	119.8	C9—C14—H14	120.1
C6—C5—H5	119.8	O4—C15—H15A	109.5
C5—C6—C1	118.6 (5)	O4—C15—H15B	109.5
C5—C6—C7	119.0 (5)	H15A—C15—H15B	109.5
C1—C6—C7	122.4 (6)	O4—C15—H15C	109.5
N1—C7—C6	120.1 (5)	H15A—C15—H15C	109.5
N1—C7—H7	119.9	H15B—C15—H15C	109.5
C6—C7—H7	119.9
C7—N1—N2—C8	176.5 (6)	N1—N2—C8—O2	−7.8 (9)
O1—C1—C2—C3	−178.4 (7)	N1—N2—C8—C9	173.5 (5)
C6—C1—C2—C3	1.1 (12)	O2—C8—C9—C10	−21.6 (9)
C1—C2—C3—C4	−1.8 (12)	N2—C8—C9—C10	157.1 (6)
C2—C3—C4—C5	1.8 (10)	O2—C8—C9—C14	157.4 (6)
C2—C3—C4—I1	178.9 (6)	N2—C8—C9—C14	−23.9 (8)
C3—C4—C5—C6	−1.2 (10)	C14—C9—C10—C11	4.3 (10)
I1—C4—C5—C6	−178.2 (5)	C8—C9—C10—C11	−176.6 (6)
C4—C5—C6—C1	0.5 (10)	C9—C10—C11—C12	−2.8 (11)
C4—C5—C6—C7	179.5 (6)	C10—C11—C12—O3	177.0 (7)
O1—C1—C6—C5	179.0 (7)	C10—C11—C12—C13	0.1 (10)
C2—C1—C6—C5	−0.4 (11)	O3—C12—C13—C14	−175.6 (6)
O1—C1—C6—C7	0.0 (11)	C11—C12—C13—C14	1.1 (10)
C2—C1—C6—C7	−179.5 (7)	C12—C13—C14—C9	0.4 (10)
N2—N1—C7—C6	177.6 (6)	C10—C9—C14—C13	−3.1 (10)
C5—C6—C7—N1	179.2 (6)	C8—C9—C14—C13	177.9 (6)
C1—C6—C7—N1	−1.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.607 (8)	146
N2—H2···O4	0.86	2.06	2.897 (7)	164
O3—H3···O2i	0.82	1.90	2.712 (6)	171
O4—H4···O2ii	0.82	2.05	2.868 (7)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.89	2.607 (8)	146
N2—H2⋯O4	0.86	2.06	2.897 (7)	164
O3—H3⋯O2i	0.82	1.90	2.712 (6)	171
O4—H4⋯O2ii	0.82	2.05	2.868 (7)	177

Symmetry codes: (i) ; (ii) .