(E)-2-(Isonicotinoylhydrazonometh-yl)benzoic acid methanol monosolvate.

The title compound, C(14)H(11)N(3)O(3)·CH(4)O, was synthesized by the condensation reaction of isonicotinohydrazide with an equimolar quantity of 2-formyl-benzoic acid in methanol. The hydrazone mol-ecule displays an E configuration about the C=N bond. The dihedral angel between the pyridine and the benzene rings is 12.04 (5)°. In the crystal structure, mol-ecules are linked by O-H⋯N, O-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

Related literature

For general background to hydrazones, see: Dhande et al. (2007 ▶). For a related structure, see: Zhang et al. (2009 ▶).

Experimental

Crystal data

C14H11N3O3·CH4O

M = 301.30

Monoclinic,

a = 6.9768 (11) Å

b = 12.2103 (13) Å

c = 17.2650 (19) Å

β = 95.497 (1)°

V = 1464.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.43 × 0.19 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.985

7290 measured reflections

2508 independent reflections

1233 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 0.99

2508 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809038902/bq2160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038902/bq2160Isup2.hkl

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

C14H11N3O3·CH4O	F(000) = 632
Mr = 301.30	Dx = 1.367 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1170 reflections
a = 6.9768 (11) Å	θ = 2.4–21.5°
b = 12.2103 (13) Å	µ = 0.10 mm−1
c = 17.2650 (19) Å	T = 298 K
β = 95.497 (1)°	Block, yellow
V = 1464.0 (3) Å3	0.43 × 0.19 × 0.15 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	2508 independent reflections
Radiation source: fine-focus sealed tube	1233 reflections with I > 2σ(I)
graphite	Rint = 0.076
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.958, Tmax = 0.985	k = −12→14
7290 measured reflections	l = −19→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3
2508 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.2762 (4)	0.52906 (18)	0.52873 (12)	0.0371 (7)
H1	0.3076	0.5854	0.5570	0.045*
N2	0.2993 (4)	0.42528 (18)	0.55868 (14)	0.0390 (7)
N3	0.1111 (4)	0.8638 (2)	0.36585 (14)	0.0438 (7)
O1	0.1643 (3)	0.46359 (16)	0.41058 (12)	0.0537 (7)
O2	0.5588 (3)	0.46550 (16)	0.77984 (11)	0.0523 (7)
H2	0.5752	0.5125	0.8137	0.078*
O3	0.4040 (4)	0.38081 (18)	0.86917 (13)	0.0654 (8)
O4	0.4701 (4)	0.3132 (2)	0.38940 (15)	0.0876 (10)
H4	0.3697	0.3467	0.3775	0.131*
C1	0.2034 (5)	0.5407 (2)	0.45415 (17)	0.0361 (8)
C2	0.1221 (5)	0.8462 (3)	0.44169 (18)	0.0474 (9)
H2A	0.1103	0.9057	0.4745	0.057*
C3	0.1501 (5)	0.7440 (2)	0.47459 (17)	0.0406 (9)
H3	0.1551	0.7347	0.5282	0.049*
C4	0.1704 (4)	0.6558 (2)	0.42630 (15)	0.0312 (7)
C5	0.1561 (5)	0.6736 (2)	0.34726 (16)	0.0380 (8)
H5	0.1660	0.6155	0.3131	0.046*
C6	0.1271 (5)	0.7785 (3)	0.31942 (18)	0.0429 (9)
H6	0.1183	0.7900	0.2659	0.052*
C7	0.3532 (4)	0.4180 (2)	0.63048 (16)	0.0347 (8)
H7	0.3768	0.4809	0.6602	0.042*
C8	0.3783 (4)	0.3093 (2)	0.66650 (17)	0.0322 (8)
C9	0.4202 (5)	0.2943 (2)	0.74724 (17)	0.0353 (8)
C10	0.4338 (5)	0.1888 (2)	0.77718 (19)	0.0456 (9)
H10	0.4572	0.1786	0.8306	0.055*
C11	0.4133 (5)	0.0993 (3)	0.7289 (2)	0.0548 (10)
H11	0.4255	0.0290	0.7496	0.066*
C12	0.3750 (5)	0.1135 (3)	0.6503 (2)	0.0551 (10)
H12	0.3624	0.0530	0.6175	0.066*
C13	0.3551 (5)	0.2177 (2)	0.61980 (18)	0.0434 (9)
H13	0.3254	0.2264	0.5665	0.052*
C14	0.4585 (5)	0.3846 (3)	0.80510 (18)	0.0416 (9)
C15	0.4316 (6)	0.2034 (3)	0.3937 (2)	0.0742 (13)
H15A	0.4264	0.1828	0.4471	0.111*
H15B	0.5314	0.1626	0.3720	0.111*
H15C	0.3101	0.1879	0.3648	0.111*

	U11	U22	U33	U12	U13	U23
N1	0.0488 (19)	0.0284 (14)	0.0325 (15)	0.0004 (13)	−0.0045 (13)	0.0009 (11)
N2	0.0479 (19)	0.0308 (14)	0.0365 (15)	−0.0022 (13)	−0.0049 (13)	0.0049 (12)
N3	0.046 (2)	0.0452 (16)	0.0389 (16)	0.0059 (14)	−0.0003 (13)	0.0045 (13)
O1	0.076 (2)	0.0369 (12)	0.0436 (13)	0.0013 (12)	−0.0172 (12)	−0.0072 (11)
O2	0.078 (2)	0.0419 (13)	0.0375 (13)	−0.0119 (13)	0.0066 (12)	−0.0091 (10)
O3	0.099 (2)	0.0622 (16)	0.0371 (14)	0.0029 (15)	0.0188 (14)	0.0043 (12)
O4	0.091 (3)	0.0691 (19)	0.096 (2)	−0.0088 (17)	−0.0259 (17)	−0.0136 (15)
C1	0.041 (2)	0.0362 (18)	0.0302 (17)	0.0006 (16)	−0.0025 (15)	−0.0011 (14)
C2	0.063 (3)	0.045 (2)	0.0339 (19)	0.0114 (18)	0.0027 (16)	−0.0026 (15)
C3	0.055 (3)	0.0425 (19)	0.0232 (17)	0.0076 (17)	0.0002 (16)	0.0029 (14)
C4	0.030 (2)	0.0366 (17)	0.0266 (16)	0.0033 (14)	0.0013 (13)	−0.0005 (13)
C5	0.041 (2)	0.0438 (19)	0.0284 (17)	0.0048 (16)	0.0018 (15)	−0.0019 (14)
C6	0.046 (2)	0.054 (2)	0.0286 (18)	0.0026 (18)	−0.0005 (16)	0.0094 (16)
C7	0.041 (2)	0.0315 (17)	0.0309 (17)	−0.0005 (15)	−0.0007 (14)	0.0031 (13)
C8	0.028 (2)	0.0290 (17)	0.0388 (18)	−0.0009 (14)	0.0007 (14)	0.0024 (14)
C9	0.034 (2)	0.0332 (17)	0.0374 (18)	0.0021 (15)	−0.0006 (15)	0.0079 (14)
C10	0.051 (2)	0.041 (2)	0.044 (2)	0.0005 (17)	0.0033 (17)	0.0115 (16)
C11	0.061 (3)	0.0333 (19)	0.069 (3)	−0.0039 (18)	0.001 (2)	0.0131 (18)
C12	0.067 (3)	0.032 (2)	0.066 (2)	−0.0038 (18)	0.001 (2)	−0.0039 (18)
C13	0.048 (3)	0.0372 (19)	0.0430 (19)	−0.0029 (17)	−0.0059 (17)	−0.0002 (15)
C14	0.050 (2)	0.0410 (19)	0.0329 (18)	0.0089 (18)	0.0001 (16)	0.0054 (15)
C15	0.085 (4)	0.058 (3)	0.077 (3)	−0.005 (2)	−0.004 (2)	−0.007 (2)

N1—C1	1.346 (3)	C5—C6	1.376 (4)
N1—N2	1.372 (3)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—C7	1.264 (3)	C7—C8	1.469 (4)
N3—C2	1.322 (4)	C7—H7	0.9300
N3—C6	1.325 (4)	C8—C13	1.380 (4)
O1—C1	1.219 (3)	C8—C9	1.409 (4)
O2—C14	1.309 (4)	C9—C10	1.388 (4)
O2—H2	0.8200	C9—C14	1.495 (4)
O3—C14	1.205 (3)	C10—C11	1.374 (4)
O4—C15	1.371 (4)	C10—H10	0.9300
O4—H4	0.8200	C11—C12	1.369 (4)
C1—O1	1.219 (3)	C11—H11	0.9300
C1—C4	1.496 (4)	C12—C13	1.378 (4)
C2—C3	1.377 (4)	C12—H12	0.9300
C2—H2A	0.9300	C13—H13	0.9300
C3—C4	1.377 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.376 (4)	C15—H15C	0.9600
C1—N1—N2	118.6 (2)	C8—C7—H7	120.3
C1—N1—H1	120.7	C13—C8—C9	118.3 (3)
N2—N1—H1	120.7	C13—C8—C7	118.9 (3)
C7—N2—N1	116.6 (2)	C9—C8—C7	122.8 (3)
C2—N3—C6	118.1 (3)	C10—C9—C8	119.3 (3)
C14—O2—H2	109.5	C10—C9—C14	115.7 (3)
C15—O4—H4	109.5	C8—C9—C14	124.9 (3)
O1—C1—N1	123.4 (3)	C11—C10—C9	120.9 (3)
O1—C1—N1	123.4 (3)	C11—C10—H10	119.6
O1—C1—C4	120.6 (3)	C9—C10—H10	119.6
O1—C1—C4	120.6 (3)	C12—C11—C10	120.0 (3)
N1—C1—C4	116.0 (3)	C12—C11—H11	120.0
N3—C2—C3	123.3 (3)	C10—C11—H11	120.0
N3—C2—H2A	118.4	C11—C12—C13	119.9 (3)
C3—C2—H2A	118.4	C11—C12—H12	120.0
C2—C3—C4	118.5 (3)	C13—C12—H12	120.0
C2—C3—H3	120.7	C12—C13—C8	121.6 (3)
C4—C3—H3	120.7	C12—C13—H13	119.2
C5—C4—C3	118.3 (3)	C8—C13—H13	119.2
C5—C4—C1	117.5 (2)	O3—C14—O2	124.1 (3)
C3—C4—C1	124.2 (2)	O3—C14—C9	122.2 (3)
C6—C5—C4	119.2 (3)	O2—C14—C9	113.7 (3)
C6—C5—H5	120.4	O4—C15—H15A	109.5
C4—C5—H5	120.4	O4—C15—H15B	109.5
N3—C6—C5	122.5 (3)	H15A—C15—H15B	109.5
N3—C6—H6	118.7	O4—C15—H15C	109.5
C5—C6—H6	118.7	H15A—C15—H15C	109.5
N2—C7—C8	119.4 (3)	H15B—C15—H15C	109.5
N2—C7—H7	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.86	2.13	2.891 (3)	148
O4—H4···O1	0.82	2.14	2.864 (4)	148
O2—H2···N3ii	0.82	1.76	2.565 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.86	2.13	2.891 (3)	148
O4—H4⋯O1	0.82	2.14	2.864 (4)	148
O2—H2⋯N3ii	0.82	1.76	2.565 (3)	165

Symmetry codes: (i) ; (ii) .