N-(2-Meth-oxy-phen-yl)phthalamic acid.

The title compound, C14H13NO3, adopts a twisted conformation in the crystal, with an inter-planar angle between the two benzene rings of 87.30 (5)°. Mol-ecules within the structure are linked via O-H⋯O inter-actions, forming a hydrogen-bonded chain motif with graph set C(7) along the glide plane in the [001] direction.

Related literature

For related phthalamic acid structures, see: Smith et al. (1983 ▶) and Bocelli et al. (1989 ▶). For the structure of a diaryl amide containing the 2-meth­oxy­phenyl moeity, see: Parra et al. (2001 ▶). A description of hydrogen bonding in terms of graph sets is given by Etter (1990 ▶) and Bernstein et al. (1995) ▶. For standard bond lengths as calculated using crystal structure data, see Allen et al. (2006 ▶).

Experimental

Crystal data

C15H13NO4

M = 271.26

Monoclinic,

a = 9.038 (4) Å

b = 14.237 (5) Å

c = 10.405 (4) Å

β = 107.456 (5)°

V = 1277.2 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.53 × 0.18 × 0.09 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.978, T max = 0.991

9056 measured reflections

2904 independent reflections

2687 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.111

S = 1.09

2904 reflections

233 parameters

All H-atom parameters refined

Δρmax = 0.30 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013408/gw2134sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013408/gw2134Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013408/gw2134Isup3.cml

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

C15H13NO4	F(000) = 568
Mr = 271.26	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3461 reflections
a = 9.038 (4) Å	θ = 2.5–33.2°
b = 14.237 (5) Å	µ = 0.10 mm−1
c = 10.405 (4) Å	T = 120 K
β = 107.456 (5)°	Prism, colorless
V = 1277.2 (9) Å3	0.53 × 0.18 × 0.09 mm
Z = 4

Rigaku Saturn724+ diffractometer	2904 independent reflections
Radiation source: Sealed Tube	2687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.8°
profile data from ω–scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→18
Tmin = 0.978, Tmax = 0.991	l = −8→13
9056 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	All H-atom parameters refined
S = 1.09	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.4728P] where P = (Fo2 + 2Fc2)/3
2904 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.38628 (15)	0.07876 (9)	0.59059 (13)	0.0212 (3)
C2	0.45227 (14)	0.03553 (9)	0.71557 (13)	0.0204 (3)
C3	0.42309 (16)	−0.05935 (9)	0.73260 (14)	0.0230 (3)
C4	0.32498 (17)	−0.10968 (9)	0.62659 (14)	0.0258 (3)
C5	0.25493 (17)	−0.06637 (10)	0.50393 (14)	0.0261 (3)
C6	0.28625 (16)	0.02755 (10)	0.48532 (13)	0.0239 (3)
C7	0.42837 (15)	0.17822 (9)	0.57121 (13)	0.0221 (3)
C8	0.55286 (15)	0.08745 (9)	0.83745 (13)	0.0209 (3)
C9	0.83209 (15)	0.12208 (9)	0.95264 (13)	0.0228 (3)
C10	0.97791 (16)	0.11002 (9)	0.93125 (14)	0.0243 (3)
C11	1.11088 (17)	0.14262 (10)	1.02478 (15)	0.0299 (3)
C12	1.09965 (19)	0.18763 (11)	1.14052 (16)	0.0356 (4)
C13	0.95702 (19)	0.20079 (10)	1.16090 (15)	0.0325 (3)
C14	0.82184 (17)	0.16842 (10)	1.06717 (14)	0.0264 (3)
C15	1.11647 (18)	0.05563 (12)	0.78206 (18)	0.0324 (3)
N1	0.70557 (13)	0.08237 (8)	0.85182 (12)	0.0237 (2)
O1	0.37604 (13)	0.20728 (7)	0.44416 (10)	0.0297 (2)
O2	0.50580 (14)	0.22662 (7)	0.66190 (11)	0.0353 (3)
O3	0.49670 (11)	0.12378 (7)	0.91995 (9)	0.0251 (2)
O4	0.97329 (11)	0.06458 (7)	0.81392 (10)	0.0278 (2)
H1N	0.731 (2)	0.0563 (13)	0.7835 (19)	0.034 (5)*
H1O	0.425 (3)	0.2672 (18)	0.440 (2)	0.062 (7)*
H3	0.481 (2)	−0.0877 (12)	0.8217 (19)	0.032 (4)*
H4	0.304 (2)	−0.1725 (13)	0.6414 (17)	0.028 (4)*
H5	0.185 (2)	−0.1009 (13)	0.4320 (18)	0.032 (4)*
H6	0.2416 (18)	0.0616 (11)	0.4002 (16)	0.019 (4)*
H11	1.209 (2)	0.1333 (13)	1.0088 (18)	0.037 (5)*
H12	1.194 (3)	0.2081 (15)	1.203 (2)	0.048 (6)*
H13	0.944 (2)	0.2302 (13)	1.2380 (19)	0.035 (5)*
H14	0.728 (2)	0.1778 (12)	1.0829 (17)	0.026 (4)*
H15A	1.088 (2)	0.0212 (14)	0.694 (2)	0.044 (5)*
H15B	1.158 (2)	0.1163 (14)	0.7720 (19)	0.039 (5)*
H15C	1.192 (2)	0.0199 (13)	0.8516 (18)	0.033 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0216 (6)	0.0207 (6)	0.0216 (6)	0.0001 (5)	0.0070 (5)	−0.0006 (5)
C2	0.0187 (6)	0.0220 (6)	0.0215 (6)	0.0009 (5)	0.0074 (5)	−0.0014 (5)
C3	0.0226 (6)	0.0225 (6)	0.0230 (6)	0.0005 (5)	0.0051 (5)	0.0006 (5)
C4	0.0277 (7)	0.0205 (6)	0.0294 (7)	−0.0033 (5)	0.0090 (6)	−0.0023 (5)
C5	0.0264 (7)	0.0257 (6)	0.0243 (7)	−0.0045 (5)	0.0050 (5)	−0.0058 (5)
C6	0.0245 (7)	0.0259 (6)	0.0202 (6)	−0.0001 (5)	0.0051 (5)	−0.0014 (5)
C7	0.0229 (6)	0.0211 (6)	0.0217 (6)	0.0006 (5)	0.0056 (5)	−0.0003 (5)
C8	0.0227 (6)	0.0185 (5)	0.0202 (6)	0.0010 (5)	0.0047 (5)	0.0006 (5)
C9	0.0242 (7)	0.0199 (6)	0.0211 (6)	−0.0019 (5)	0.0020 (5)	0.0019 (5)
C10	0.0263 (7)	0.0210 (6)	0.0240 (6)	−0.0002 (5)	0.0051 (5)	0.0038 (5)
C11	0.0236 (7)	0.0285 (7)	0.0333 (8)	−0.0028 (5)	0.0020 (6)	0.0045 (6)
C12	0.0324 (8)	0.0316 (7)	0.0329 (8)	−0.0074 (6)	−0.0052 (6)	0.0002 (6)
C13	0.0429 (9)	0.0263 (7)	0.0241 (7)	−0.0045 (6)	0.0034 (6)	−0.0052 (6)
C14	0.0294 (7)	0.0239 (6)	0.0246 (7)	−0.0011 (5)	0.0059 (6)	−0.0009 (5)
C15	0.0252 (7)	0.0351 (8)	0.0393 (9)	0.0056 (6)	0.0134 (6)	0.0062 (7)
N1	0.0217 (6)	0.0283 (6)	0.0207 (6)	−0.0011 (4)	0.0058 (4)	−0.0063 (4)
O1	0.0356 (6)	0.0259 (5)	0.0240 (5)	−0.0053 (4)	0.0036 (4)	0.0033 (4)
O2	0.0497 (7)	0.0240 (5)	0.0263 (5)	−0.0099 (4)	0.0026 (5)	0.0002 (4)
O3	0.0253 (5)	0.0269 (5)	0.0238 (5)	0.0014 (4)	0.0083 (4)	−0.0054 (4)
O4	0.0225 (5)	0.0342 (5)	0.0277 (5)	0.0002 (4)	0.0091 (4)	−0.0024 (4)

C1—C6	1.3980 (19)	C9—C10	1.411 (2)
C1—C2	1.4001 (18)	C9—N1	1.4171 (17)
C1—C7	1.4955 (18)	C10—O4	1.3711 (17)
C2—C3	1.3977 (19)	C10—C11	1.380 (2)
C2—C8	1.5131 (18)	C11—C12	1.394 (2)
C3—C4	1.3891 (19)	C11—H11	0.961 (19)
C3—H3	1.002 (18)	C12—C13	1.381 (2)
C4—C5	1.387 (2)	C12—H12	0.95 (2)
C4—H4	0.937 (18)	C13—C14	1.393 (2)
C5—C6	1.392 (2)	C13—H13	0.942 (19)
C5—H5	0.956 (19)	C14—H14	0.920 (17)
C6—H6	0.984 (16)	C15—O4	1.4346 (18)
C7—O2	1.2079 (17)	C15—H15A	1.00 (2)
C7—O1	1.3293 (17)	C15—H15B	0.96 (2)
C8—O3	1.2343 (16)	C15—H15C	0.975 (19)
C8—N1	1.3449 (19)	N1—H1N	0.889 (19)
C9—C14	1.389 (2)	O1—H1O	0.97 (3)
C6—C1—C2	119.58 (12)	O4—C10—C11	125.02 (13)
C6—C1—C7	121.26 (12)	O4—C10—C9	114.67 (12)
C2—C1—C7	119.13 (12)	C11—C10—C9	120.31 (13)
C3—C2—C1	119.91 (12)	C10—C11—C12	119.33 (14)
C3—C2—C8	117.04 (11)	C10—C11—H11	119.1 (11)
C1—C2—C8	123.03 (12)	C12—C11—H11	121.6 (12)
C4—C3—C2	119.84 (12)	C13—C12—C11	120.55 (14)
C4—C3—H3	123.9 (10)	C13—C12—H12	122.4 (13)
C2—C3—H3	116.2 (10)	C11—C12—H12	117.1 (13)
C5—C4—C3	120.51 (13)	C12—C13—C14	120.71 (15)
C5—C4—H4	121.1 (11)	C12—C13—H13	123.3 (11)
C3—C4—H4	118.3 (11)	C14—C13—H13	115.9 (11)
C4—C5—C6	119.94 (13)	C9—C14—C13	119.17 (14)
C4—C5—H5	120.2 (11)	C9—C14—H14	121.5 (11)
C6—C5—H5	119.9 (11)	C13—C14—H14	119.3 (11)
C5—C6—C1	120.17 (13)	O4—C15—H15A	104.6 (12)
C5—C6—H6	123.6 (9)	O4—C15—H15B	110.8 (11)
C1—C6—H6	116.2 (9)	H15A—C15—H15B	110.0 (16)
O2—C7—O1	123.32 (12)	O4—C15—H15C	110.7 (11)
O2—C7—C1	123.10 (12)	H15A—C15—H15C	110.7 (16)
O1—C7—C1	113.56 (11)	H15B—C15—H15C	110.0 (16)
O3—C8—N1	124.58 (12)	C8—N1—C9	129.36 (12)
O3—C8—C2	121.24 (12)	C8—N1—H1N	115.7 (12)
N1—C8—C2	113.92 (11)	C9—N1—H1N	114.5 (12)
C14—C9—C10	119.92 (13)	C7—O1—H1O	106.7 (14)
C14—C9—N1	125.29 (13)	C10—O4—C15	117.33 (12)
C10—C9—N1	114.78 (12)
C6—C1—C2—C3	2.71 (19)	C1—C2—C8—N1	−93.21 (15)
C7—C1—C2—C3	−175.39 (12)	C14—C9—C10—O4	−179.05 (12)
C6—C1—C2—C8	−175.73 (12)	N1—C9—C10—O4	2.14 (16)
C7—C1—C2—C8	6.17 (18)	C14—C9—C10—C11	1.1 (2)
C1—C2—C3—C4	−1.92 (19)	N1—C9—C10—C11	−177.70 (12)
C8—C2—C3—C4	176.61 (12)	O4—C10—C11—C12	−179.85 (13)
C2—C3—C4—C5	−0.3 (2)	C9—C10—C11—C12	0.0 (2)
C3—C4—C5—C6	1.8 (2)	C10—C11—C12—C13	−0.9 (2)
C4—C5—C6—C1	−1.0 (2)	C11—C12—C13—C14	0.8 (2)
C2—C1—C6—C5	−1.3 (2)	C10—C9—C14—C13	−1.2 (2)
C7—C1—C6—C5	176.80 (12)	N1—C9—C14—C13	177.44 (13)
C6—C1—C7—O2	174.83 (14)	C12—C13—C14—C9	0.3 (2)
C2—C1—C7—O2	−7.1 (2)	O3—C8—N1—C9	−5.9 (2)
C6—C1—C7—O1	−6.92 (18)	C2—C8—N1—C9	179.87 (12)
C2—C1—C7—O1	171.15 (11)	C14—C9—N1—C8	6.6 (2)
C3—C2—C8—O3	−86.11 (16)	C10—C9—N1—C8	−174.66 (13)
C1—C2—C8—O3	92.37 (16)	C11—C10—O4—C15	−4.18 (19)
C3—C2—C8—N1	88.31 (14)	C9—C10—O4—C15	176.00 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3i	0.97 (3)	1.72 (3)	2.6837 (16)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3i	0.97 (3)	1.72 (3)	2.6837 (16)	175 (2)

Symmetry code: (i) .