2-[(5-Chloro-2-oxidobenzyl-idene)aza-nium-yl]-2-methyl-propane-1,3-diol.

The title compound, C(11)H(14)ClNO(3), was prepared by the condensation of equimolar quanti-ties of 5-chloro-salicyl-aldehyde and 2-amino-2-methyl-propane-1,3-diol in methanol. In the crystal, it exists in the zwitterionic form, with nominal proton transfer from the phenol group to the imine N atom. This results in the formation of an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring. Inter-molecular O-H⋯O hydrogen bonds arise from the hy-droxy groups, forming (001) sheets.

Related literature

For a related structure we have reported recently and for background to Schiff bases, see: Wang et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H14ClNO3

M = 243.68

Orthorhombic,

a = 6.0019 (16) Å

b = 8.838 (3) Å

c = 21.555 (3) Å

V = 1143.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 298 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.968

5744 measured reflections

2105 independent reflections

1745 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.076

S = 1.05

2105 reflections

155 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 842 Friedel pairs

Flack parameter: −0.06 (8)

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055784/hb6578sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055784/hb6578Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055784/hb6578Isup3.cml

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

C11H14ClNO3	Dx = 1.416 Mg m−3
Mr = 243.68	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1733 reflections
a = 6.0019 (16) Å	θ = 2.5–24.2°
b = 8.838 (3) Å	µ = 0.33 mm−1
c = 21.555 (3) Å	T = 298 K
V = 1143.4 (5) Å3	Block, yellow
Z = 4	0.13 × 0.12 × 0.10 mm
F(000) = 512

Bruker SMART 1K CCD diffractometer	2105 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scan	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→7
Tmin = 0.959, Tmax = 0.968	k = −10→10
5744 measured reflections	l = −26→21

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0287P)2 + 0.113P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2105 reflections	Δρmax = 0.17 e Å−3
155 parameters	Δρmin = −0.15 e Å−3
3 restraints	Absolute structure: Flack (1983), 842 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (8)

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	0.67835 (15)	−0.07637 (8)	−0.02077 (3)	0.0613 (2)
N1	0.8677 (3)	0.4851 (2)	0.15414 (9)	0.0356 (5)
O1	1.2095 (3)	0.30421 (19)	0.14623 (7)	0.0422 (4)
O3	0.5214 (3)	0.6832 (2)	0.27003 (8)	0.0462 (5)
O4	1.0926 (3)	0.6167 (2)	0.24842 (11)	0.0609 (6)
C1	1.0897 (4)	0.2197 (3)	0.11037 (11)	0.0350 (6)
C2	1.1701 (5)	0.0789 (3)	0.08645 (11)	0.0442 (6)
H2	1.3107	0.0449	0.0981	0.053*
C3	1.0452 (5)	−0.0064 (3)	0.04693 (12)	0.0470 (7)
H3	1.1032	−0.0965	0.0316	0.056*
C4	0.8320 (5)	0.0388 (3)	0.02898 (11)	0.0412 (6)
C5	0.7447 (4)	0.1709 (3)	0.05062 (10)	0.0366 (6)
H5	0.6031	0.2012	0.0383	0.044*
C6	0.8698 (4)	0.2620 (3)	0.09192 (10)	0.0315 (5)
C7	0.7671 (4)	0.3945 (3)	0.11616 (10)	0.0352 (6)
H7	0.6219	0.4170	0.1042	0.042*
C8	0.7731 (4)	0.6211 (3)	0.18423 (10)	0.0350 (6)
C9	0.6345 (6)	0.7147 (3)	0.13884 (12)	0.0603 (8)
H9A	0.7202	0.7341	0.1021	0.090*
H9B	0.5940	0.8089	0.1579	0.090*
H9C	0.5020	0.6598	0.1280	0.090*
C10	0.6293 (4)	0.5634 (3)	0.23840 (11)	0.0384 (6)
H10A	0.5181	0.4938	0.2226	0.046*
H10B	0.7229	0.5085	0.2674	0.046*
C11	0.9699 (4)	0.7115 (3)	0.20833 (12)	0.0462 (7)
H11A	1.0627	0.7446	0.1741	0.055*
H11B	0.9180	0.8002	0.2306	0.055*
H3A	0.603 (4)	0.720 (3)	0.2983 (10)	0.069*
H4	1.215 (3)	0.651 (3)	0.2621 (12)	0.069*
H1	1.005 (2)	0.452 (3)	0.1646 (11)	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0825 (6)	0.0435 (4)	0.0579 (4)	−0.0035 (4)	−0.0139 (4)	−0.0124 (3)
N1	0.0328 (13)	0.0364 (11)	0.0375 (11)	0.0047 (10)	−0.0019 (11)	−0.0049 (9)
O1	0.0355 (11)	0.0420 (10)	0.0492 (10)	0.0030 (8)	−0.0089 (9)	0.0012 (8)
O3	0.0260 (10)	0.0535 (11)	0.0593 (13)	0.0027 (9)	−0.0050 (9)	−0.0220 (9)
O4	0.0310 (11)	0.0618 (13)	0.0897 (15)	−0.0013 (10)	−0.0201 (11)	−0.0092 (12)
C1	0.0362 (16)	0.0340 (13)	0.0349 (13)	−0.0015 (11)	0.0023 (11)	0.0063 (11)
C2	0.0376 (15)	0.0406 (14)	0.0543 (15)	0.0119 (14)	0.0050 (14)	0.0048 (13)
C3	0.0590 (19)	0.0330 (13)	0.0491 (16)	0.0070 (14)	0.0076 (15)	−0.0023 (13)
C4	0.0514 (17)	0.0346 (13)	0.0376 (13)	−0.0026 (13)	−0.0027 (13)	−0.0006 (11)
C5	0.0362 (16)	0.0358 (13)	0.0377 (13)	−0.0003 (11)	0.0001 (12)	0.0000 (11)
C6	0.0285 (14)	0.0331 (12)	0.0329 (12)	0.0010 (11)	0.0026 (11)	0.0009 (11)
C7	0.0318 (14)	0.0378 (13)	0.0360 (13)	0.0002 (11)	0.0009 (11)	−0.0011 (11)
C8	0.0351 (15)	0.0286 (12)	0.0412 (13)	0.0039 (11)	−0.0039 (12)	−0.0041 (10)
C9	0.076 (2)	0.0487 (16)	0.0564 (17)	0.0194 (16)	−0.0117 (16)	0.0018 (14)
C10	0.0296 (14)	0.0332 (12)	0.0524 (15)	−0.0012 (12)	0.0023 (12)	−0.0090 (12)
C11	0.0412 (17)	0.0391 (14)	0.0585 (17)	−0.0131 (13)	0.0074 (15)	−0.0071 (13)

Cl1—C4	1.743 (2)	C4—C5	1.362 (3)
N1—C7	1.294 (3)	C5—C6	1.416 (3)
N1—C8	1.479 (3)	C5—H5	0.9300
N1—H1	0.903 (10)	C6—C7	1.423 (3)
O1—C1	1.293 (3)	C7—H7	0.9300
O3—C10	1.416 (3)	C8—C11	1.517 (3)
O3—H3A	0.847 (10)	C8—C9	1.528 (3)
O4—C11	1.411 (3)	C8—C10	1.539 (3)
O4—H4	0.847 (10)	C9—H9A	0.9600
C1—C6	1.428 (3)	C9—H9B	0.9600
C1—C2	1.431 (3)	C9—H9C	0.9600
C2—C3	1.362 (3)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.395 (4)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C7—N1—C8	126.9 (2)	C6—C7—H7	118.7
C7—N1—H1	112.7 (17)	N1—C8—C11	106.2 (2)
C8—N1—H1	120.1 (17)	N1—C8—C9	111.61 (19)
C10—O3—H3A	112 (2)	C11—C8—C9	111.0 (2)
C11—O4—H4	117 (2)	N1—C8—C10	106.20 (18)
O1—C1—C6	121.9 (2)	C11—C8—C10	110.55 (19)
O1—C1—C2	122.0 (2)	C9—C8—C10	111.1 (2)
C6—C1—C2	116.1 (2)	C8—C9—H9A	109.5
C3—C2—C1	121.4 (2)	C8—C9—H9B	109.5
C3—C2—H2	119.3	H9A—C9—H9B	109.5
C1—C2—H2	119.3	C8—C9—H9C	109.5
C2—C3—C4	121.3 (2)	H9A—C9—H9C	109.5
C2—C3—H3	119.3	H9B—C9—H9C	109.5
C4—C3—H3	119.3	O3—C10—C8	111.98 (19)
C5—C4—C3	120.2 (2)	O3—C10—H10A	109.2
C5—C4—Cl1	120.5 (2)	C8—C10—H10A	109.2
C3—C4—Cl1	119.27 (19)	O3—C10—H10B	109.2
C4—C5—C6	119.9 (2)	C8—C10—H10B	109.2
C4—C5—H5	120.0	H10A—C10—H10B	107.9
C6—C5—H5	120.0	O4—C11—C8	107.65 (19)
C5—C6—C7	118.0 (2)	O4—C11—H11A	110.2
C5—C6—C1	121.1 (2)	C8—C11—H11A	110.2
C7—C6—C1	120.9 (2)	O4—C11—H11B	110.2
N1—C7—C6	122.6 (2)	C8—C11—H11B	110.2
N1—C7—H7	118.7	H11A—C11—H11B	108.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.90 (1)	1.84 (2)	2.606 (3)	142 (2)
O4—H4···O3i	0.85 (1)	1.87 (1)	2.680 (2)	160 (3)
O3—H3A···O1ii	0.85 (1)	1.80 (1)	2.648 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.90 (1)	1.84 (2)	2.606 (3)	142 (2)
O4—H4⋯O3i	0.85 (1)	1.87 (1)	2.680 (2)	160 (3)
O3—H3A⋯O1ii	0.85 (1)	1.80 (1)	2.648 (2)	176 (3)

Symmetry codes: (i) ; (ii) .