Crystal structure of (E)-2-[(4-hy-droxy-benzyl-idene)aza-nium-yl]benzoate.

The title Schiff base, C14H11NO3, crystallizes as a zwitterion (i.e. proton transfer from the carb-oxy-lic acid group to the imine N atom). The dihedral angle between the aromatic rings is 19.59 (6)° and an intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (4)(24) loops. The dimers are linked by C-H⋯O inter-actions, generating (211) sheets.

Related literature

For related structures, see: Hang et al. (2010 ▶); Ligtenbarg et al. (1999 ▶); Trzesowska-Kruszynska (2010 ▶).

Experimental

Crystal data

C14H11NO3

M = 241.24

Monoclinic,

a = 3.8612 (5) Å

b = 15.280 (3) Å

c = 18.604 (3) Å

β = 90.347 (8)°

V = 1097.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.38 × 0.17 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.962, T max = 0.985

17364 measured reflections

2089 independent reflections

1363 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.124

S = 1.15

2089 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814018273/hb7268sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018273/hb7268Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018273/hb7268Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018273/hb7268fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line represents the intra­molecular H-bond.

Click here for additional data file.

. DOI: 10.1107/S1600536814018273/hb7268fig2.tif

The partial packing, which shows that mol­ecules form dimers which are inter­linked.

CCDC reference: 1018737

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H11NO3	F(000) = 504
Mr = 241.24	Dx = 1.460 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.8612 (5) Å	Cell parameters from 1363 reflections
b = 15.280 (3) Å	θ = 1.8–26.0°
c = 18.604 (3) Å	µ = 0.10 mm−1
β = 90.347 (8)°	T = 296 K
V = 1097.6 (3) Å3	Cut needle, yellow
Z = 4	0.38 × 0.17 × 0.15 mm

Bruker Kappa APEXII CCD diffractometer	2089 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −18→18
Tmin = 0.962, Tmax = 0.985	l = −22→22
17364 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0187P)2 + 1.0858P] where P = (Fo2 + 2Fc2)/3
2089 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.23 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
O1	0.1341 (6)	−0.08844 (13)	0.32981 (10)	0.0469 (6)
O2	0.0144 (7)	−0.18735 (14)	0.24574 (12)	0.0580 (7)
O3	0.6380 (6)	0.22716 (14)	0.59807 (11)	0.0489 (6)
H3A	0.701 (9)	0.177 (2)	0.6251 (19)	0.073*
N1	−0.0068 (6)	0.07058 (16)	0.30803 (13)	0.0360 (6)
H1	0.067 (7)	0.016 (2)	0.3337 (15)	0.043*
C1	0.0114 (8)	−0.1120 (2)	0.26817 (16)	0.0394 (7)
C2	−0.1414 (7)	−0.04003 (18)	0.22116 (14)	0.0328 (7)
C3	−0.2813 (8)	−0.0637 (2)	0.15519 (15)	0.0398 (7)
H3	−0.2817	−0.1223	0.1417	0.048*
C4	−0.4196 (8)	−0.0021 (2)	0.10915 (16)	0.0460 (8)
H4	−0.5103	−0.0192	0.0649	0.055*
C5	−0.4233 (8)	0.0847 (2)	0.12868 (16)	0.0461 (8)
H5	−0.5171	0.1261	0.0975	0.055*
C6	−0.2890 (8)	0.1107 (2)	0.19417 (16)	0.0416 (8)
H6	−0.2931	0.1694	0.2074	0.050*
C7	−0.1485 (7)	0.04873 (18)	0.23973 (14)	0.0332 (7)
C8	0.0590 (7)	0.14802 (19)	0.33225 (15)	0.0370 (7)
H8	0.0125	0.1955	0.3025	0.044*
C9	0.1993 (7)	0.16514 (18)	0.40216 (15)	0.0342 (7)
C10	0.2987 (7)	0.25053 (19)	0.41916 (16)	0.0384 (7)
H10	0.2674	0.2947	0.3854	0.046*
C11	0.4416 (8)	0.27050 (19)	0.48472 (16)	0.0397 (7)
H11	0.5063	0.3278	0.4950	0.048*
C12	0.4901 (8)	0.20511 (19)	0.53595 (15)	0.0365 (7)
C13	0.3814 (7)	0.12005 (18)	0.52047 (15)	0.0375 (7)
H13	0.4051	0.0764	0.5550	0.045*
C14	0.2400 (8)	0.10038 (19)	0.45483 (15)	0.0376 (7)
H14	0.1700	0.0433	0.4451	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0702 (15)	0.0380 (12)	0.0324 (12)	0.0036 (11)	−0.0144 (11)	0.0019 (9)
O2	0.0942 (19)	0.0323 (12)	0.0474 (14)	0.0034 (13)	−0.0117 (13)	−0.0025 (11)
O3	0.0679 (16)	0.0367 (13)	0.0419 (13)	−0.0001 (11)	−0.0187 (11)	−0.0015 (10)
N1	0.0437 (15)	0.0313 (14)	0.0329 (13)	0.0036 (11)	−0.0026 (11)	−0.0010 (11)
C1	0.0498 (19)	0.0336 (17)	0.0347 (17)	−0.0006 (14)	0.0009 (15)	0.0032 (14)
C2	0.0340 (16)	0.0343 (16)	0.0300 (15)	0.0000 (13)	0.0007 (13)	0.0007 (12)
C3	0.0438 (18)	0.0382 (18)	0.0374 (17)	−0.0019 (14)	−0.0049 (14)	−0.0030 (14)
C4	0.0479 (19)	0.056 (2)	0.0344 (18)	0.0010 (16)	−0.0085 (15)	−0.0005 (15)
C5	0.050 (2)	0.048 (2)	0.0400 (18)	0.0060 (16)	−0.0051 (16)	0.0115 (16)
C6	0.0443 (19)	0.0354 (17)	0.0452 (19)	0.0038 (14)	−0.0015 (15)	0.0032 (14)
C7	0.0370 (17)	0.0347 (17)	0.0278 (15)	−0.0001 (13)	−0.0005 (13)	0.0003 (12)
C8	0.0401 (17)	0.0319 (16)	0.0390 (17)	0.0000 (13)	−0.0009 (14)	0.0033 (14)
C9	0.0350 (16)	0.0313 (16)	0.0362 (16)	0.0019 (13)	−0.0024 (13)	−0.0017 (13)
C10	0.0439 (18)	0.0305 (16)	0.0407 (18)	0.0027 (14)	−0.0066 (14)	0.0064 (13)
C11	0.0461 (18)	0.0271 (16)	0.0457 (19)	−0.0011 (13)	−0.0075 (15)	−0.0018 (14)
C12	0.0389 (17)	0.0359 (17)	0.0345 (16)	0.0020 (13)	−0.0027 (14)	−0.0028 (13)
C13	0.0472 (19)	0.0289 (16)	0.0365 (17)	0.0018 (14)	0.0006 (14)	0.0047 (13)
C14	0.0442 (18)	0.0280 (16)	0.0404 (17)	−0.0022 (13)	0.0000 (14)	−0.0035 (13)

O1—C1	1.289 (3)	C5—H5	0.9300
O2—C1	1.225 (3)	C6—C7	1.380 (4)
O3—C12	1.329 (3)	C6—H6	0.9300
O3—H3A	0.95 (4)	C8—C9	1.430 (4)
N1—C8	1.291 (3)	C8—H8	0.9300
N1—C7	1.420 (3)	C9—C10	1.396 (4)
N1—H1	1.00 (3)	C9—C14	1.401 (4)
C1—C2	1.522 (4)	C10—C11	1.370 (4)
C2—C3	1.386 (4)	C10—H10	0.9300
C2—C7	1.400 (4)	C11—C12	1.393 (4)
C3—C4	1.378 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.395 (4)
C4—C5	1.375 (4)	C13—C14	1.368 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (4)	C14—H14	0.9300
C12—O3—H3A	111 (2)	C6—C7—N1	122.4 (3)
C8—N1—C7	127.0 (3)	C2—C7—N1	116.1 (2)
C8—N1—H1	122.7 (16)	N1—C8—C9	123.9 (3)
C7—N1—H1	109.9 (16)	N1—C8—H8	118.0
O2—C1—O1	124.2 (3)	C9—C8—H8	118.0
O2—C1—C2	119.2 (3)	C10—C9—C14	118.2 (3)
O1—C1—C2	116.6 (3)	C10—C9—C8	118.6 (3)
C3—C2—C7	117.6 (3)	C14—C9—C8	123.2 (3)
C3—C2—C1	117.9 (3)	C11—C10—C9	121.2 (3)
C7—C2—C1	124.5 (2)	C11—C10—H10	119.4
C4—C3—C2	121.4 (3)	C9—C10—H10	119.4
C4—C3—H3	119.3	C10—C11—C12	120.1 (3)
C2—C3—H3	119.3	C10—C11—H11	120.0
C5—C4—C3	119.9 (3)	C12—C11—H11	120.0
C5—C4—H4	120.0	O3—C12—C11	117.9 (3)
C3—C4—H4	120.0	O3—C12—C13	122.9 (3)
C4—C5—C6	120.5 (3)	C11—C12—C13	119.2 (3)
C4—C5—H5	119.8	C14—C13—C12	120.5 (3)
C6—C5—H5	119.8	C14—C13—H13	119.8
C5—C6—C7	119.2 (3)	C12—C13—H13	119.8
C5—C6—H6	120.4	C13—C14—C9	120.8 (3)
C7—C6—H6	120.4	C13—C14—H14	119.6
C6—C7—C2	121.4 (3)	C9—C14—H14	119.6
O2—C1—C2—C3	1.9 (4)	C8—N1—C7—C6	−11.1 (5)
O1—C1—C2—C3	−178.8 (3)	C8—N1—C7—C2	169.5 (3)
O2—C1—C2—C7	−177.6 (3)	C7—N1—C8—C9	179.4 (3)
O1—C1—C2—C7	1.7 (4)	N1—C8—C9—C10	172.3 (3)
C7—C2—C3—C4	0.6 (4)	N1—C8—C9—C14	−8.1 (5)
C1—C2—C3—C4	−179.0 (3)	C14—C9—C10—C11	1.9 (4)
C2—C3—C4—C5	−0.6 (5)	C8—C9—C10—C11	−178.6 (3)
C3—C4—C5—C6	0.1 (5)	C9—C10—C11—C12	0.0 (5)
C4—C5—C6—C7	0.4 (5)	C10—C11—C12—O3	178.3 (3)
C5—C6—C7—C2	−0.4 (4)	C10—C11—C12—C13	−2.1 (4)
C5—C6—C7—N1	−179.7 (3)	O3—C12—C13—C14	−178.0 (3)
C3—C2—C7—C6	0.0 (4)	C11—C12—C13—C14	2.3 (4)
C1—C2—C7—C6	179.5 (3)	C12—C13—C14—C9	−0.5 (4)
C3—C2—C7—N1	179.3 (3)	C10—C9—C14—C13	−1.6 (4)
C1—C2—C7—N1	−1.2 (4)	C8—C9—C14—C13	178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1i	0.95 (4)	1.71 (4)	2.656 (3)	173 (3)
N1—H1···O1	1.00 (3)	1.62 (3)	2.522 (3)	148 (2)
C6—H6···O2ii	0.93	2.51	3.397 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1i	0.95 (4)	1.71 (4)	2.656 (3)	173 (3)
N1—H1⋯O1	1.00 (3)	1.62 (3)	2.522 (3)	148 (2)
C6—H6⋯O2ii	0.93	2.51	3.397 (4)	160

Symmetry codes: (i) ; (ii) .