8-[(1E)-1-(2-Aminophenyl-iminio)eth-yl]-2-oxo-2H-chromen-7-olate.

The title Schiff base, C(17)H(14)N(2)O(3), exists as an NH tautomer with the H atom of the phenol group transferred to the imine N atom. The iminium H atom is involved in a strong intra-molecular N(+)-H⋯O(-) hydrogen bond to the phenolate O atom, forming an S(6) motif. In the crystal structure, N-H⋯O hydrogen bonds form a C(9) chain parallel to [100] and a C(11) chain parallel to [010], while C-H⋯O hydrogen bonds form a C(11) chain parallel to [010]. The combination of N-H⋯O and C-H⋯O hydrogen bonds generates R(4) (3)(30) rings parallel to the ab plane.

Related literature

For related structures, see: Patil et al. (2010 ▶); Aazam et al. (2006 ▶); Filarowski (2005 ▶); El Husseiny et al. (2008 ▶); Aazam et al. (2008 ▶); Karabıyık et al. (2008 ▶). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H14N2O3

M = 294.30

Orthorhombic,

a = 7.5462 (3) Å

b = 18.9324 (11) Å

c = 20.0445 (9) Å

V = 2863.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.44 × 0.29 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.962, T max = 0.984

25561 measured reflections

2868 independent reflections

1972 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.095

S = 1.00

2868 reflections

212 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023093/gk2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023093/gk2282Isup2.hkl

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

C17H14N2O3	F(000) = 1232
Mr = 294.30	Dx = 1.365 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25561 reflections
a = 7.5462 (3) Å	θ = 2.0–26.7°
b = 18.9324 (11) Å	µ = 0.10 mm−1
c = 20.0445 (9) Å	T = 296 K
V = 2863.7 (2) Å3	Prism, yellow
Z = 8	0.44 × 0.29 × 0.20 mm

Stoe IPDS 2 diffractometer	2868 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
graphite	Rint = 0.039
rotation method scans	θmax = 26.2°, θmin = 2.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.962, Tmax = 0.984	k = −23→23
25561 measured reflections	l = −24→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0515P)2 + ] where P = (Fo2 + 2Fc2)/3
2868 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.15 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
C1	0.3733 (2)	0.81253 (7)	0.38471 (7)	0.0462 (4)
C2	0.5193 (2)	0.83854 (7)	0.41971 (8)	0.0487 (4)
C3	0.4876 (2)	0.89106 (8)	0.46724 (8)	0.0584 (4)
H3	0.5822	0.9095	0.4914	0.070*
C4	0.3197 (3)	0.91605 (8)	0.47909 (9)	0.0632 (5)
H4	0.3019	0.9507	0.5113	0.076*
C5	0.1777 (3)	0.89021 (9)	0.44379 (9)	0.0646 (5)
H5	0.0642	0.9073	0.4519	0.077*
C6	0.2051 (2)	0.83870 (8)	0.39613 (9)	0.0581 (4)
H6	0.1098	0.8215	0.3716	0.070*
C7	0.44310 (18)	0.69702 (7)	0.33766 (7)	0.0446 (3)
C8	0.4588 (2)	0.66606 (8)	0.40572 (8)	0.0602 (4)
H8A	0.4121	0.6987	0.4379	0.072*
H8B	0.5813	0.6569	0.4154	0.072*
H8C	0.3932	0.6227	0.4077	0.072*
C9	0.47034 (19)	0.65822 (7)	0.27529 (7)	0.0442 (3)
C10	0.4368 (2)	0.69219 (7)	0.21251 (8)	0.0491 (4)
C11	0.4623 (2)	0.65452 (8)	0.15220 (8)	0.0584 (4)
H11	0.4402	0.6767	0.1117	0.070*
C12	0.5186 (2)	0.58675 (8)	0.15284 (9)	0.0587 (4)
H12	0.5332	0.5630	0.1126	0.070*
C13	0.5555 (2)	0.55134 (7)	0.21273 (8)	0.0525 (4)
C14	0.53174 (19)	0.58766 (7)	0.27212 (8)	0.0455 (4)
C15	0.6172 (2)	0.48034 (8)	0.21610 (10)	0.0641 (5)
H15	0.6307	0.4548	0.1768	0.077*
C16	0.6561 (2)	0.44943 (8)	0.27412 (10)	0.0671 (5)
H16	0.6943	0.4027	0.2746	0.081*
C17	0.6397 (2)	0.48719 (7)	0.33552 (10)	0.0588 (4)
N1	0.39971 (17)	0.76316 (6)	0.33146 (7)	0.0488 (3)
N2	0.68956 (19)	0.81302 (8)	0.41013 (8)	0.0631 (4)
O1	0.38245 (16)	0.75749 (5)	0.20935 (6)	0.0603 (3)
O2	0.67878 (17)	0.46798 (5)	0.39135 (7)	0.0735 (4)
O3	0.57044 (14)	0.55503 (5)	0.33133 (5)	0.0541 (3)
H1	0.390 (3)	0.7742 (10)	0.2853 (8)	0.087 (6)*
H2A	0.715 (2)	0.7907 (9)	0.3703 (10)	0.071 (5)*
H2B	0.772 (3)	0.8469 (11)	0.4178 (11)	0.099 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0615 (9)	0.0363 (7)	0.0409 (9)	−0.0009 (6)	0.0025 (7)	0.0007 (6)
C2	0.0586 (9)	0.0435 (7)	0.0439 (9)	−0.0018 (7)	0.0053 (7)	−0.0002 (6)
C3	0.0700 (11)	0.0557 (8)	0.0494 (10)	−0.0061 (8)	0.0042 (8)	−0.0116 (7)
C4	0.0844 (13)	0.0537 (9)	0.0515 (10)	0.0048 (8)	0.0143 (9)	−0.0090 (7)
C5	0.0651 (10)	0.0662 (10)	0.0623 (12)	0.0133 (8)	0.0086 (9)	−0.0029 (9)
C6	0.0586 (10)	0.0577 (9)	0.0579 (11)	0.0039 (7)	−0.0008 (8)	−0.0007 (8)
C7	0.0490 (8)	0.0393 (7)	0.0454 (9)	−0.0045 (6)	−0.0014 (7)	0.0024 (6)
C8	0.0889 (12)	0.0459 (8)	0.0459 (10)	0.0056 (8)	0.0010 (9)	0.0037 (7)
C9	0.0483 (8)	0.0397 (7)	0.0446 (9)	−0.0056 (6)	−0.0026 (6)	−0.0011 (6)
C10	0.0563 (9)	0.0455 (7)	0.0454 (9)	−0.0067 (6)	−0.0048 (7)	0.0001 (6)
C11	0.0734 (11)	0.0588 (9)	0.0431 (10)	−0.0053 (8)	−0.0043 (8)	−0.0011 (7)
C12	0.0681 (10)	0.0594 (9)	0.0486 (11)	−0.0077 (8)	0.0003 (8)	−0.0134 (7)
C13	0.0544 (9)	0.0465 (8)	0.0565 (11)	−0.0054 (6)	−0.0008 (7)	−0.0097 (7)
C14	0.0474 (8)	0.0411 (7)	0.0480 (10)	−0.0076 (6)	−0.0040 (7)	0.0001 (6)
C15	0.0686 (11)	0.0489 (8)	0.0749 (13)	−0.0011 (8)	−0.0002 (10)	−0.0181 (8)
C16	0.0724 (11)	0.0416 (8)	0.0874 (15)	0.0047 (7)	−0.0082 (10)	−0.0091 (9)
C17	0.0586 (10)	0.0384 (7)	0.0795 (14)	−0.0011 (7)	−0.0101 (9)	0.0018 (8)
N1	0.0667 (8)	0.0393 (6)	0.0403 (8)	0.0007 (5)	−0.0026 (6)	−0.0012 (5)
N2	0.0562 (8)	0.0674 (9)	0.0659 (10)	−0.0034 (7)	0.0055 (8)	−0.0179 (8)
O1	0.0862 (8)	0.0476 (6)	0.0472 (7)	0.0064 (5)	−0.0074 (6)	0.0060 (5)
O2	0.0904 (9)	0.0482 (6)	0.0820 (10)	0.0054 (6)	−0.0181 (8)	0.0106 (6)
O3	0.0671 (7)	0.0391 (5)	0.0560 (7)	0.0035 (5)	−0.0068 (5)	0.0008 (5)

C1—C6	1.381 (2)	C9—C10	1.436 (2)
C1—C2	1.396 (2)	C10—O1	1.3040 (17)
C1—N1	1.4327 (18)	C10—C11	1.417 (2)
C2—N2	1.386 (2)	C11—C12	1.351 (2)
C2—C3	1.398 (2)	C11—H11	0.9300
C3—C4	1.373 (2)	C12—C13	1.403 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (3)	C13—C14	1.386 (2)
C4—H4	0.9300	C13—C15	1.424 (2)
C5—C6	1.381 (2)	C14—O3	1.3695 (17)
C5—H5	0.9300	C15—C16	1.334 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—N1	1.3004 (17)	C16—C17	1.429 (3)
C7—C9	1.464 (2)	C16—H16	0.9300
C7—C8	1.490 (2)	C17—O2	1.213 (2)
C8—H8A	0.9600	C17—O3	1.3893 (17)
C8—H8B	0.9600	N1—H1	0.952 (15)
C8—H8C	0.9600	N2—H2A	0.92 (2)
C9—C14	1.4153 (19)	N2—H2B	0.91 (2)
C6—C1—C2	121.01 (14)	O1—C10—C9	121.51 (13)
C6—C1—N1	119.04 (14)	C11—C10—C9	119.89 (13)
C2—C1—N1	119.65 (13)	C12—C11—C10	120.84 (16)
N2—C2—C1	122.62 (14)	C12—C11—H11	119.6
N2—C2—C3	120.05 (15)	C10—C11—H11	119.6
C1—C2—C3	117.31 (14)	C11—C12—C13	121.61 (15)
C4—C3—C2	121.38 (16)	C11—C12—H12	119.2
C4—C3—H3	119.3	C13—C12—H12	119.2
C2—C3—H3	119.3	C14—C13—C12	118.17 (13)
C3—C4—C5	120.51 (15)	C14—C13—C15	118.01 (16)
C3—C4—H4	119.7	C12—C13—C15	123.82 (16)
C5—C4—H4	119.7	O3—C14—C13	119.53 (13)
C4—C5—C6	119.43 (16)	O3—C14—C9	117.17 (13)
C4—C5—H5	120.3	C13—C14—C9	123.30 (14)
C6—C5—H5	120.3	C16—C15—C13	121.81 (16)
C5—C6—C1	120.36 (16)	C16—C15—H15	119.1
C5—C6—H6	119.8	C13—C15—H15	119.1
C1—C6—H6	119.8	C15—C16—C17	120.82 (15)
N1—C7—C9	115.89 (13)	C15—C16—H16	119.6
N1—C7—C8	119.11 (13)	C17—C16—H16	119.6
C9—C7—C8	124.99 (12)	O2—C17—O3	115.12 (15)
C7—C8—H8A	109.5	O2—C17—C16	128.58 (15)
C7—C8—H8B	109.5	O3—C17—C16	116.29 (16)
H8A—C8—H8B	109.5	C7—N1—C1	126.31 (13)
C7—C8—H8C	109.5	C7—N1—H1	108.9 (11)
H8A—C8—H8C	109.5	C1—N1—H1	124.8 (11)
H8B—C8—H8C	109.5	C2—N2—H2A	118.0 (11)
C14—C9—C10	116.18 (13)	C2—N2—H2B	111.5 (13)
C14—C9—C7	123.89 (13)	H2A—N2—H2B	109.3 (17)
C10—C9—C7	119.92 (12)	C14—O3—C17	123.35 (13)
O1—C10—C11	118.60 (14)
C6—C1—C2—N2	179.24 (15)	C11—C12—C13—C15	−179.15 (16)
N1—C1—C2—N2	−7.1 (2)	C12—C13—C14—O3	−178.55 (13)
C6—C1—C2—C3	1.0 (2)	C15—C13—C14—O3	1.0 (2)
N1—C1—C2—C3	174.61 (13)	C12—C13—C14—C9	0.8 (2)
N2—C2—C3—C4	−178.25 (16)	C15—C13—C14—C9	−179.68 (14)
C1—C2—C3—C4	0.0 (2)	C10—C9—C14—O3	177.82 (12)
C2—C3—C4—C5	−0.5 (3)	C7—C9—C14—O3	−1.3 (2)
C3—C4—C5—C6	0.0 (3)	C10—C9—C14—C13	−1.5 (2)
C4—C5—C6—C1	1.0 (3)	C7—C9—C14—C13	179.41 (14)
C2—C1—C6—C5	−1.5 (2)	C14—C13—C15—C16	−1.7 (2)
N1—C1—C6—C5	−175.19 (14)	C12—C13—C15—C16	177.81 (17)
N1—C7—C9—C14	174.71 (14)	C13—C15—C16—C17	−1.0 (3)
C8—C7—C9—C14	−6.3 (2)	C15—C16—C17—O2	−175.59 (18)
N1—C7—C9—C10	−4.4 (2)	C15—C16—C17—O3	4.2 (3)
C8—C7—C9—C10	174.68 (14)	C9—C7—N1—C1	−177.28 (14)
C14—C9—C10—O1	−178.93 (14)	C8—C7—N1—C1	3.6 (2)
C7—C9—C10—O1	0.2 (2)	C6—C1—N1—C7	−112.84 (17)
C14—C9—C10—C11	1.2 (2)	C2—C1—N1—C7	73.42 (19)
C7—C9—C10—C11	−179.71 (14)	C13—C14—O3—C17	2.5 (2)
O1—C10—C11—C12	179.96 (15)	C9—C14—O3—C17	−176.83 (13)
C9—C10—C11—C12	−0.1 (2)	O2—C17—O3—C14	174.78 (14)
C10—C11—C12—C13	−0.7 (3)	C16—C17—O3—C14	−5.1 (2)
C11—C12—C13—C14	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.95 (2)	1.56 (2)	2.4534 (17)	155 (2)
N2—H2A···O1i	0.92 (2)	2.13 (2)	2.9933 (19)	154.7 (15)
N2—H2B···O2ii	0.91 (2)	2.37 (2)	3.1203 (19)	138.7 (17)
C5—H5···O2iii	0.93	2.48	3.242 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.95 (2)	1.56 (2)	2.4534 (17)	155 (2)
N2—H2A⋯O1i	0.92 (2)	2.13 (2)	2.9933 (19)	154.7 (15)
N2—H2B⋯O2ii	0.91 (2)	2.37 (2)	3.1203 (19)	138.7 (17)
C5—H5⋯O2iii	0.93	2.48	3.242 (2)	139

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