2-{[(E)-1,3-Benzodioxol-5-yl]methyl-idene-amino}-benzoic acid.

In the title compound, C(15)H(11)NO(4), the dihedral angle between the aromatic rings is 23.8 (2)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For a related structure, see: Yang et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11NO4

M = 269.25

Orthorhombic,

a = 22.884 (2) Å

b = 3.9402 (4) Å

c = 13.5696 (13) Å

V = 1223.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.28 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.988

28104 measured reflections

1152 independent reflections

925 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.122

S = 1.12

1152 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038420/hb5653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038420/hb5653Isup2.hkl

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

C15H11NO4	F(000) = 560
Mr = 269.25	Dx = 1.462 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 925 reflections
a = 22.884 (2) Å	θ = 2.3–25.2°
b = 3.9402 (4) Å	µ = 0.11 mm−1
c = 13.5696 (13) Å	T = 296 K
V = 1223.5 (2) Å3	Needle, orange yellow
Z = 4	0.28 × 0.14 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	1152 independent reflections
Radiation source: fine-focus sealed tube	925 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 8.20 pixels mm-1	θmax = 25.2°, θmin = 2.3°
ω scans	h = −27→27
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −4→4
Tmin = 0.980, Tmax = 0.988	l = −16→16
28104 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.1607P] where P = (Fo2 + 2Fc2)/3
1152 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.51893 (16)	0.1333 (11)	0.1270 (2)	0.0783 (14)
O2	0.60847 (16)	0.3309 (12)	0.1082 (3)	0.0870 (16)
O3	0.28294 (13)	−0.2221 (9)	0.0939 (2)	0.0644 (11)
O4	0.22350 (12)	−0.5110 (9)	0.2031 (3)	0.0615 (11)
N1	0.47183 (15)	0.1225 (8)	0.2968 (3)	0.0477 (11)
C1	0.5677 (2)	0.2642 (12)	0.1623 (3)	0.0597 (17)
C2	0.56974 (18)	0.3361 (10)	0.2714 (3)	0.0453 (12)
C3	0.62059 (19)	0.4809 (11)	0.3079 (4)	0.0557 (16)
C4	0.6268 (2)	0.5551 (12)	0.4064 (4)	0.0603 (17)
C5	0.5811 (2)	0.4898 (11)	0.4697 (4)	0.0613 (17)
C6	0.53019 (19)	0.3494 (11)	0.4360 (3)	0.0550 (16)
C7	0.52366 (16)	0.2630 (10)	0.3363 (3)	0.0427 (12)
C8	0.43348 (17)	−0.0263 (9)	0.3505 (3)	0.0487 (12)
C9	0.37893 (17)	−0.1565 (9)	0.3122 (3)	0.0453 (12)
C10	0.36230 (17)	−0.1111 (11)	0.2122 (3)	0.0480 (12)
C11	0.30981 (17)	−0.2372 (11)	0.1848 (3)	0.0463 (12)
C12	0.27312 (17)	−0.4075 (11)	0.2501 (3)	0.0477 (14)
C13	0.28753 (18)	−0.4521 (11)	0.3468 (4)	0.0520 (14)
C14	0.34183 (19)	−0.3234 (11)	0.3770 (3)	0.0520 (14)
C15	0.2282 (2)	−0.3962 (14)	0.1039 (4)	0.0650 (17)
H1	0.491 (3)	0.140 (15)	0.166 (5)	0.0937*
H3	0.65112	0.52880	0.26487	0.0668*
H4	0.66140	0.64831	0.43000	0.0722*
H5	0.58489	0.54176	0.53624	0.0734*
H6	0.49957	0.31078	0.47961	0.0655*
H8	0.44114	−0.05185	0.41734	0.0582*
H10	0.38644	0.00051	0.16763	0.0575*
H13	0.26261	−0.56229	0.39043	0.0623*
H14	0.35328	−0.35079	0.44231	0.0623*
H15A	0.19620	−0.24411	0.08841	0.0780*
H15B	0.22671	−0.58749	0.05902	0.0780*

	U11	U22	U33	U12	U13	U23
O1	0.071 (2)	0.130 (3)	0.034 (2)	−0.009 (2)	−0.0057 (16)	−0.008 (2)
O2	0.074 (2)	0.143 (4)	0.044 (2)	−0.012 (2)	0.0141 (19)	−0.003 (2)
O3	0.0587 (18)	0.094 (2)	0.0405 (18)	−0.0102 (18)	−0.0039 (15)	0.0052 (17)
O4	0.0574 (17)	0.080 (2)	0.047 (2)	−0.0098 (16)	−0.0032 (15)	0.0034 (18)
N1	0.0472 (19)	0.055 (2)	0.041 (2)	0.0002 (16)	0.0019 (17)	0.0018 (17)
C1	0.055 (3)	0.079 (3)	0.045 (3)	0.000 (2)	−0.002 (2)	0.004 (2)
C2	0.052 (2)	0.049 (2)	0.035 (2)	0.0056 (19)	0.0013 (18)	0.0029 (18)
C3	0.053 (2)	0.065 (3)	0.049 (3)	−0.002 (2)	0.002 (2)	−0.001 (2)
C4	0.057 (3)	0.068 (3)	0.056 (3)	−0.007 (2)	−0.011 (2)	−0.002 (2)
C5	0.079 (3)	0.062 (3)	0.043 (3)	−0.008 (3)	−0.007 (3)	−0.008 (2)
C6	0.063 (3)	0.059 (2)	0.043 (3)	−0.003 (2)	0.004 (2)	−0.002 (2)
C7	0.048 (2)	0.044 (2)	0.036 (2)	0.0044 (18)	−0.0005 (18)	0.0011 (16)
C8	0.055 (2)	0.049 (2)	0.042 (2)	0.007 (2)	0.000 (2)	0.002 (2)
C9	0.048 (2)	0.047 (2)	0.041 (2)	0.0048 (18)	0.0014 (19)	0.0020 (18)
C10	0.050 (2)	0.054 (2)	0.040 (2)	0.0019 (19)	0.006 (2)	0.0058 (19)
C11	0.052 (2)	0.054 (2)	0.033 (2)	0.009 (2)	0.0016 (19)	−0.0006 (19)
C12	0.045 (2)	0.055 (2)	0.043 (3)	−0.0001 (19)	0.0020 (19)	−0.001 (2)
C13	0.056 (2)	0.055 (2)	0.045 (3)	0.000 (2)	0.006 (2)	0.006 (2)
C14	0.056 (2)	0.054 (2)	0.046 (3)	0.008 (2)	0.006 (2)	0.010 (2)
C15	0.067 (3)	0.082 (3)	0.046 (3)	−0.003 (3)	−0.005 (2)	0.006 (2)

O1—C1	1.320 (6)	C9—C14	1.388 (6)
O2—C1	1.216 (6)	C9—C10	1.421 (6)
O3—C11	1.380 (5)	C10—C11	1.352 (6)
O3—C15	1.435 (6)	C11—C12	1.393 (6)
O4—C12	1.365 (5)	C12—C13	1.364 (7)
O4—C15	1.424 (7)	C13—C14	1.403 (6)
O1—H1	0.83 (7)	C3—H3	0.9300
N1—C7	1.414 (5)	C4—H4	0.9300
N1—C8	1.283 (5)	C5—H5	0.9300
C1—C2	1.508 (6)	C6—H6	0.9300
C2—C7	1.404 (6)	C8—H8	0.9300
C2—C3	1.387 (6)	C10—H10	0.9300
C3—C4	1.376 (8)	C13—H13	0.9300
C4—C5	1.378 (7)	C14—H14	0.9300
C5—C6	1.368 (6)	C15—H15A	0.9700
C6—C7	1.403 (6)	C15—H15B	0.9700
C8—C9	1.446 (5)
C11—O3—C15	106.5 (3)	C11—C12—C13	121.9 (4)
C12—O4—C15	106.5 (3)	O4—C12—C11	110.4 (4)
C1—O1—H1	114 (5)	C12—C13—C14	116.6 (4)
C7—N1—C8	122.5 (4)	C9—C14—C13	121.9 (4)
O1—C1—O2	121.0 (4)	O3—C15—O4	107.9 (4)
O1—C1—C2	117.1 (4)	C2—C3—H3	119.00
O2—C1—C2	121.9 (4)	C4—C3—H3	119.00
C1—C2—C3	117.0 (4)	C3—C4—H4	120.00
C1—C2—C7	123.7 (4)	C5—C4—H4	120.00
C3—C2—C7	119.4 (4)	C4—C5—H5	120.00
C2—C3—C4	121.4 (4)	C6—C5—H5	120.00
C3—C4—C5	119.2 (4)	C5—C6—H6	120.00
C4—C5—C6	120.9 (5)	C7—C6—H6	120.00
C5—C6—C7	120.7 (4)	N1—C8—H8	118.00
N1—C7—C2	118.2 (4)	C9—C8—H8	118.00
N1—C7—C6	123.4 (4)	C9—C10—H10	121.00
C2—C7—C6	118.4 (4)	C11—C10—H10	122.00
N1—C8—C9	123.3 (4)	C12—C13—H13	122.00
C8—C9—C14	117.9 (4)	C14—C13—H13	122.00
C10—C9—C14	120.1 (4)	C9—C14—H14	119.00
C8—C9—C10	122.0 (4)	C13—C14—H14	119.00
C9—C10—C11	117.0 (4)	O3—C15—H15A	110.00
O3—C11—C10	128.8 (4)	O3—C15—H15B	110.00
O3—C11—C12	108.7 (3)	O4—C15—H15A	110.00
C10—C11—C12	122.5 (4)	O4—C15—H15B	110.00
O4—C12—C13	127.7 (4)	H15A—C15—H15B	109.00
C15—O3—C11—C10	179.6 (5)	C3—C4—C5—C6	0.7 (7)
C15—O3—C11—C12	−1.2 (5)	C4—C5—C6—C7	1.1 (7)
C11—O3—C15—O4	0.5 (5)	C5—C6—C7—N1	−178.9 (4)
C15—O4—C12—C11	−1.1 (5)	C5—C6—C7—C2	−2.4 (6)
C15—O4—C12—C13	178.3 (5)	N1—C8—C9—C10	−3.7 (6)
C12—O4—C15—O3	0.4 (5)	N1—C8—C9—C14	177.8 (4)
C8—N1—C7—C2	162.9 (4)	C8—C9—C10—C11	−178.7 (4)
C8—N1—C7—C6	−20.6 (6)	C14—C9—C10—C11	−0.2 (6)
C7—N1—C8—C9	176.8 (3)	C8—C9—C14—C13	178.7 (4)
O1—C1—C2—C3	−178.6 (4)	C10—C9—C14—C13	0.2 (6)
O1—C1—C2—C7	1.8 (6)	C9—C10—C11—O3	178.6 (4)
O2—C1—C2—C3	−0.4 (7)	C9—C10—C11—C12	−0.5 (6)
O2—C1—C2—C7	−180.0 (5)	O3—C11—C12—O4	1.5 (5)
C1—C2—C3—C4	−179.8 (4)	O3—C11—C12—C13	−178.0 (4)
C7—C2—C3—C4	−0.1 (6)	C10—C11—C12—O4	−179.3 (4)
C1—C2—C7—N1	−1.8 (6)	C10—C11—C12—C13	1.3 (7)
C1—C2—C7—C6	−178.5 (4)	O4—C12—C13—C14	179.4 (4)
C3—C2—C7—N1	178.6 (4)	C11—C12—C13—C14	−1.2 (6)
C3—C2—C7—C6	1.9 (6)	C12—C13—C14—C9	0.5 (6)
C2—C3—C4—C5	−1.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.83 (7)	1.83 (7)	2.544 (5)	143 (7)
C14—H14···O2i	0.93	2.42	3.337 (6)	170
C15—H15A···O2ii	0.97	2.60	3.532 (6)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.83 (7)	1.83 (7)	2.544 (5)	143 (7)
C14—H14⋯O2i	0.93	2.42	3.337 (6)	170
C15—H15A⋯O2ii	0.97	2.60	3.532 (6)	162

Symmetry codes: (i) ; (ii) .