2-[(E)-(2,4-Dihy-droxy-benzyl-idene)aza-nium-yl]-3-phenyl-propano-ate.

The title compound, C(16)H(15)NO(4), exists as a zwitterion in the solid state, with the carb-oxy-lic acid group being deprotonated and the imine N atom being protonated. The mol-ecule adopts an E configuration about the C=N double bond. The dihedral angle between the benzene rings is 46.34 (4)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, adjacent mol-ecules are connected by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, forming supra-molecular ribbons along the a axis.

Related literature

For details of Schiff bases and their applications, see: Dolaz et al. (2009 ▶); Kumar et al. (2010 ▶); Qiao et al. (2011 ▶); Sauri et al. (2009 ▶); Tamami & Ghasemi (2011 ▶). For related structures, see: Bahron et al. (2010 ▶); Hemamalini & Fun (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H15NO4

M = 285.29

Monoclinic,

a = 9.3943 (1) Å

b = 6.8946 (1) Å

c = 20.7251 (3) Å

β = 92.065 (1)°

V = 1341.49 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.34 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.982

22479 measured reflections

6007 independent reflections

4783 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.03

6007 reflections

202 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016655/rz2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016655/rz2592Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016655/rz2592Isup3.cml

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

C16H15NO4	F(000) = 600
Mr = 285.29	Dx = 1.413 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9091 reflections
a = 9.3943 (1) Å	θ = 3.0–35.3°
b = 6.8946 (1) Å	µ = 0.10 mm−1
c = 20.7251 (3) Å	T = 100 K
β = 92.065 (1)°	Block, orange
V = 1341.49 (3) Å3	0.34 × 0.27 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6007 independent reflections
Radiation source: fine-focus sealed tube	4783 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 35.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→13
Tmin = 0.966, Tmax = 0.982	k = −8→11
22479 measured reflections	l = −33→32

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.2835P] where P = (Fo2 + 2Fc2)/3
6007 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.60361 (6)	0.80079 (9)	0.04375 (3)	0.01400 (12)
O2	0.97519 (6)	0.33854 (10)	0.05402 (3)	0.01685 (13)
O3	0.03702 (7)	0.98745 (10)	0.07713 (4)	0.01988 (14)
O4	0.26610 (7)	1.04016 (9)	0.05323 (3)	0.01783 (13)
N1	0.34885 (7)	0.69321 (10)	0.08580 (3)	0.01219 (12)
C1	0.33058 (10)	0.53563 (14)	0.25232 (4)	0.01942 (16)
H1A	0.3954	0.6401	0.2590	0.023*
C2	0.35367 (11)	0.36077 (15)	0.28493 (5)	0.02434 (19)
H2A	0.4337	0.3473	0.3139	0.029*
C3	0.26067 (12)	0.20648 (14)	0.27537 (5)	0.02416 (19)
H3A	0.2770	0.0875	0.2975	0.029*
C4	0.14316 (11)	0.22715 (13)	0.23307 (5)	0.02018 (17)
H4A	0.0792	0.1219	0.2262	0.024*
C5	0.11937 (9)	0.40174 (13)	0.20089 (4)	0.01695 (15)
H5A	0.0386	0.4150	0.1723	0.020*
C6	0.21269 (9)	0.55797 (12)	0.20999 (4)	0.01422 (14)
C7	0.18457 (9)	0.74664 (12)	0.17511 (4)	0.01563 (15)
H7A	0.2505	0.8462	0.1933	0.019*
H7B	0.0863	0.7891	0.1836	0.019*
C8	0.20180 (8)	0.73766 (12)	0.10126 (4)	0.01250 (13)
H8A	0.1359	0.6381	0.0817	0.015*
C9	0.40809 (8)	0.52254 (11)	0.09102 (4)	0.01214 (13)
H9A	0.3492	0.4173	0.1029	0.015*
C10	0.55370 (8)	0.48144 (11)	0.08037 (4)	0.01121 (13)
C11	0.65246 (8)	0.61982 (11)	0.05775 (4)	0.01132 (13)
C12	0.79342 (8)	0.56952 (12)	0.04987 (4)	0.01286 (14)
H12A	0.8591	0.6634	0.0354	0.015*
C13	0.83916 (8)	0.37933 (12)	0.06334 (4)	0.01261 (14)
C14	0.74286 (8)	0.23932 (12)	0.08580 (4)	0.01396 (14)
H14A	0.7742	0.1113	0.0955	0.017*
C15	0.60318 (8)	0.29109 (12)	0.09343 (4)	0.01367 (14)
H15A	0.5381	0.1965	0.1079	0.016*
C16	0.16518 (8)	0.93989 (12)	0.07349 (4)	0.01381 (14)
H1O1	0.6599 (16)	0.855 (2)	0.0171 (7)	0.030 (4)*
H1N1	0.3969 (16)	0.791 (2)	0.0723 (7)	0.033 (4)*
H1O2	0.999 (2)	0.196 (3)	0.0635 (8)	0.052 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0131 (2)	0.0096 (2)	0.0195 (3)	0.00209 (19)	0.0036 (2)	0.0038 (2)
O2	0.0113 (2)	0.0159 (3)	0.0236 (3)	0.0048 (2)	0.0034 (2)	0.0040 (2)
O3	0.0129 (3)	0.0170 (3)	0.0299 (3)	0.0054 (2)	0.0033 (2)	0.0064 (2)
O4	0.0165 (3)	0.0150 (3)	0.0223 (3)	0.0018 (2)	0.0054 (2)	0.0063 (2)
N1	0.0109 (3)	0.0108 (3)	0.0150 (3)	0.0021 (2)	0.0019 (2)	0.0017 (2)
C1	0.0211 (4)	0.0189 (4)	0.0182 (4)	0.0017 (3)	−0.0009 (3)	0.0003 (3)
C2	0.0292 (5)	0.0244 (4)	0.0191 (4)	0.0075 (4)	−0.0044 (3)	0.0027 (3)
C3	0.0371 (5)	0.0170 (4)	0.0186 (4)	0.0083 (4)	0.0039 (4)	0.0047 (3)
C4	0.0267 (4)	0.0136 (3)	0.0207 (4)	0.0006 (3)	0.0076 (3)	0.0013 (3)
C5	0.0179 (4)	0.0155 (3)	0.0176 (4)	0.0011 (3)	0.0031 (3)	0.0011 (3)
C6	0.0165 (3)	0.0127 (3)	0.0137 (3)	0.0024 (3)	0.0043 (3)	0.0011 (3)
C7	0.0192 (4)	0.0125 (3)	0.0156 (3)	0.0028 (3)	0.0048 (3)	0.0018 (3)
C8	0.0104 (3)	0.0113 (3)	0.0160 (3)	0.0027 (2)	0.0022 (2)	0.0023 (2)
C9	0.0118 (3)	0.0110 (3)	0.0137 (3)	0.0016 (2)	0.0013 (2)	0.0010 (2)
C10	0.0102 (3)	0.0100 (3)	0.0135 (3)	0.0013 (2)	0.0013 (2)	0.0009 (2)
C11	0.0118 (3)	0.0098 (3)	0.0123 (3)	0.0016 (2)	0.0009 (2)	0.0002 (2)
C12	0.0108 (3)	0.0117 (3)	0.0162 (3)	0.0016 (2)	0.0015 (2)	0.0011 (3)
C13	0.0114 (3)	0.0129 (3)	0.0136 (3)	0.0029 (2)	0.0003 (2)	0.0007 (2)
C14	0.0129 (3)	0.0108 (3)	0.0182 (3)	0.0027 (2)	0.0014 (3)	0.0020 (3)
C15	0.0125 (3)	0.0107 (3)	0.0179 (3)	0.0013 (2)	0.0021 (2)	0.0022 (3)
C16	0.0136 (3)	0.0122 (3)	0.0157 (3)	0.0028 (2)	0.0017 (3)	0.0029 (3)

O1—C11	1.3572 (9)	C5—H5A	0.9500
O1—H1O1	0.863 (15)	C6—C7	1.5068 (12)
O2—C13	1.3293 (10)	C7—C8	1.5461 (12)
O2—H1O2	1.025 (19)	C7—H7A	0.9900
O3—C16	1.2527 (10)	C7—H7B	0.9900
O4—C16	1.2577 (10)	C8—C16	1.5425 (11)
N1—C9	1.3045 (10)	C8—H8A	1.0000
N1—C8	1.4617 (10)	C9—C10	1.4220 (11)
N1—H1N1	0.864 (16)	C9—H9A	0.9500
C1—C2	1.3952 (13)	C10—C15	1.4152 (11)
C1—C6	1.3965 (12)	C10—C11	1.4220 (11)
C1—H1A	0.9500	C11—C12	1.3842 (11)
C2—C3	1.3863 (16)	C12—C13	1.4048 (11)
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.3921 (15)	C13—C14	1.4133 (11)
C3—H3A	0.9500	C14—C15	1.3745 (11)
C4—C5	1.3903 (13)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.3973 (12)
C11—O1—H1O1	108.9 (10)	N1—C8—C7	111.03 (6)
C13—O2—H1O2	112.1 (10)	C16—C8—C7	107.65 (6)
C9—N1—C8	125.08 (7)	N1—C8—H8A	110.1
C9—N1—H1N1	120.3 (10)	C16—C8—H8A	110.1
C8—N1—H1N1	114.6 (10)	C7—C8—H8A	110.1
C2—C1—C6	120.37 (9)	N1—C9—C10	125.23 (7)
C2—C1—H1A	119.8	N1—C9—H9A	117.4
C6—C1—H1A	119.8	C10—C9—H9A	117.4
C3—C2—C1	120.51 (9)	C15—C10—C9	117.79 (7)
C3—C2—H2A	119.7	C15—C10—C11	118.13 (7)
C1—C2—H2A	119.7	C9—C10—C11	124.07 (7)
C2—C3—C4	119.53 (9)	O1—C11—C12	121.51 (7)
C2—C3—H3A	120.2	O1—C11—C10	117.88 (7)
C4—C3—H3A	120.2	C12—C11—C10	120.60 (7)
C5—C4—C3	120.06 (9)	C11—C12—C13	119.84 (7)
C5—C4—H4A	120.0	C11—C12—H12A	120.1
C3—C4—H4A	120.0	C13—C12—H12A	120.1
C4—C5—C6	120.90 (8)	O2—C13—C12	117.22 (7)
C4—C5—H5A	119.6	O2—C13—C14	122.24 (7)
C6—C5—H5A	119.6	C12—C13—C14	120.54 (7)
C1—C6—C5	118.64 (8)	C15—C14—C13	119.06 (7)
C1—C6—C7	121.20 (8)	C15—C14—H14A	120.5
C5—C6—C7	120.17 (8)	C13—C14—H14A	120.5
C6—C7—C8	114.68 (7)	C14—C15—C10	121.81 (7)
C6—C7—H7A	108.6	C14—C15—H15A	119.1
C8—C7—H7A	108.6	C10—C15—H15A	119.1
C6—C7—H7B	108.6	O3—C16—O4	127.87 (8)
C8—C7—H7B	108.6	O3—C16—C8	114.59 (7)
H7A—C7—H7B	107.6	O4—C16—C8	117.43 (7)
N1—C8—C16	107.91 (6)
C6—C1—C2—C3	0.53 (15)	C15—C10—C11—O1	178.38 (7)
C1—C2—C3—C4	−0.27 (15)	C9—C10—C11—O1	−1.95 (12)
C2—C3—C4—C5	−0.22 (15)	C15—C10—C11—C12	−1.04 (11)
C3—C4—C5—C6	0.45 (14)	C9—C10—C11—C12	178.63 (8)
C2—C1—C6—C5	−0.29 (13)	O1—C11—C12—C13	−178.40 (7)
C2—C1—C6—C7	179.02 (8)	C10—C11—C12—C13	1.00 (12)
C4—C5—C6—C1	−0.19 (13)	C11—C12—C13—O2	179.06 (7)
C4—C5—C6—C7	−179.51 (8)	C11—C12—C13—C14	−0.93 (12)
C1—C6—C7—C8	112.09 (9)	O2—C13—C14—C15	−179.07 (8)
C5—C6—C7—C8	−68.61 (10)	C12—C13—C14—C15	0.92 (12)
C9—N1—C8—C16	−166.85 (7)	C13—C14—C15—C10	−0.99 (13)
C9—N1—C8—C7	75.39 (10)	C9—C10—C15—C14	−178.64 (8)
C6—C7—C8—N1	−63.66 (9)	C11—C10—C15—C14	1.05 (12)
C6—C7—C8—C16	178.43 (7)	N1—C8—C16—O3	172.58 (7)
C8—N1—C9—C10	−175.36 (7)	C7—C8—C16—O3	−67.51 (9)
N1—C9—C10—C15	174.78 (8)	N1—C8—C16—O4	−10.87 (10)
N1—C9—C10—C11	−4.90 (13)	C7—C8—C16—O4	109.04 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O4i	0.863 (15)	1.790 (14)	2.6302 (9)	163.9 (15)
N1—H1N1···O1	0.864 (14)	2.051 (15)	2.6810 (9)	129.1 (12)
O2—H1O2···O3ii	1.03 (2)	1.51 (2)	2.5310 (10)	179 (2)
C5—H5A···O2iii	0.95	2.56	3.3155 (10)	137
C12—H12A···O2iv	0.95	2.46	3.1781 (10)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O4i	0.863 (15)	1.790 (14)	2.6302 (9)	163.9 (15)
N1—H1N1⋯O1	0.864 (14)	2.051 (15)	2.6810 (9)	129.1 (12)
O2—H1O2⋯O3ii	1.03 (2)	1.51 (2)	2.5310 (10)	179 (2)
C5—H5A⋯O2iii	0.95	2.56	3.3155 (10)	137
C12—H12A⋯O2iv	0.95	2.46	3.1781 (10)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .