2-Aminoterephthalic acid dimethyl ester.

Single crystals of the title compound, C(10)H(11)NO(4), an inter-mediate in the industrial synthesis of yellow azo pigments, were obtained from the industrial production. The mol-ecules crystallize as centrosymmetic dimers connected by two symmetry-related N-H⋯O=C hydrogen bonds. Each mol-ecule also contains an intra-molecular N-H⋯O=C hydrogen bond. The dimers form stacks along the a-axis direction. Neighbouring stacks are arranged into a herringbone structure.

Related literature

For studies on amino­terephthalic acid esters, see: Wegscheider et al. (1912 ▶); Clark et al. (1995 ▶); O’Connor et al. (1999 ▶); Lavalette et al. (2002 ▶); Jones et al. (2008 ▶). For syntheses wherein the title compound is used, see: Cordier & Coulet (1994 ▶); Metz & Weber (1999 ▶); Stengel-Rutkowski & Metz (2000 ▶); Jung et al. (2001 ▶); Herbst & Hunger (2004 ▶); Schweikart et al. (2007 ▶). For the crystal structure of the final product, Pigment Yellow 213, see: Schmidt et al. (2009 ▶).

Experimental

Crystal data

C10H11NO4

M = 209.20

Monoclinic,

a = 4.7721 (12) Å

b = 16.928 (5) Å

c = 11.841 (5) Å

β = 93.88 (5)°

V = 954.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 166 K

0.75 × 0.32 × 0.04 mm

Data collection

Siemens SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.760, T max = 0.995

11829 measured reflections

1687 independent reflections

884 reflections with I > 2σ(I)

R int = 0.140

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.134

S = 0.96

1687 reflections

146 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036095/fk2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036095/fk2004Isup2.hkl

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

C10H11NO4	F(000) = 440
Mr = 209.20	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 57 reflections
a = 4.7721 (12) Å	θ = 3–23°
b = 16.928 (5) Å	µ = 0.11 mm−1
c = 11.841 (5) Å	T = 166 K
β = 93.88 (5)°	Plate, colourless
V = 954.4 (6) Å3	0.75 × 0.32 × 0.04 mm
Z = 4

Siemens SMART 1K CCD diffractometer	1687 independent reflections
Radiation source: normal-focus sealed tube	884 reflections with I > 2σ(I)
graphite	Rint = 0.140
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −5→5
Tmin = 0.760, Tmax = 0.995	k = −20→20
11829 measured reflections	l = −14→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3
1687 reflections	(Δ/σ)max = 0.005
146 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.24 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
O1	−0.2268 (4)	0.60319 (11)	0.30114 (17)	0.0341 (6)
O2	−0.1912 (5)	0.58551 (12)	0.11612 (18)	0.0421 (7)
O3	0.7681 (5)	0.32502 (11)	0.44342 (17)	0.0328 (6)
O4	0.8629 (4)	0.29952 (12)	0.26489 (18)	0.0333 (6)
N1	0.5292 (7)	0.36927 (18)	0.0986 (3)	0.0402 (8)
C1	0.4228 (7)	0.40860 (18)	0.1867 (3)	0.0280 (8)
C2	0.2108 (7)	0.46595 (17)	0.1622 (3)	0.0298 (8)
H2A	0.1487	0.4762	0.0857	0.036*
C3	0.0944 (6)	0.50678 (17)	0.2471 (3)	0.0258 (8)
C4	0.1783 (6)	0.49355 (17)	0.3592 (3)	0.0287 (8)
H4A	0.0967	0.5224	0.4175	0.034*
C5	0.3823 (6)	0.43779 (17)	0.3851 (2)	0.0277 (8)
H5A	0.4401	0.4281	0.4622	0.033*
C6	0.5072 (6)	0.39497 (17)	0.3004 (3)	0.0263 (8)
C7	−0.1217 (7)	0.56897 (17)	0.2121 (3)	0.0281 (8)
C8	−0.4282 (6)	0.66622 (18)	0.2753 (3)	0.0386 (9)
H8A	−0.3290	0.7134	0.2514	0.058*
H8B	−0.5277	0.6785	0.3429	0.058*
H8C	−0.5636	0.6492	0.2142	0.058*
C9	0.7296 (7)	0.33575 (17)	0.3320 (3)	0.0267 (8)
C10	0.9869 (7)	0.26942 (18)	0.4801 (3)	0.0381 (9)
H10A	0.9394	0.2170	0.4495	0.057*
H10B	1.0030	0.2670	0.5630	0.057*
H10C	1.1661	0.2867	0.4527	0.057*
H1A	0.702 (9)	0.348 (2)	0.120 (3)	0.074 (14)*
H1B	0.482 (7)	0.385 (2)	0.023 (3)	0.059 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0400 (15)	0.0187 (12)	0.0440 (14)	0.0105 (11)	0.0066 (11)	0.0034 (10)
O2	0.0606 (18)	0.0258 (14)	0.0392 (15)	0.0091 (12)	−0.0009 (12)	0.0034 (11)
O3	0.0391 (13)	0.0174 (11)	0.0416 (14)	0.0065 (11)	0.0000 (11)	0.0041 (10)
O4	0.0396 (14)	0.0177 (12)	0.0431 (14)	0.0031 (11)	0.0068 (11)	−0.0042 (10)
N1	0.049 (2)	0.0357 (19)	0.0361 (19)	0.0125 (16)	0.0027 (17)	−0.0045 (15)
C1	0.032 (2)	0.0169 (17)	0.0351 (19)	−0.0029 (16)	0.0028 (16)	−0.0014 (14)
C2	0.034 (2)	0.0208 (18)	0.0347 (19)	−0.0019 (16)	0.0017 (16)	0.0027 (15)
C3	0.0273 (19)	0.0148 (17)	0.0354 (19)	−0.0035 (15)	0.0038 (15)	0.0009 (14)
C4	0.037 (2)	0.0129 (17)	0.036 (2)	−0.0012 (16)	0.0058 (16)	−0.0015 (14)
C5	0.035 (2)	0.0139 (17)	0.0334 (18)	−0.0036 (15)	−0.0004 (15)	0.0010 (14)
C6	0.0305 (19)	0.0109 (16)	0.0376 (19)	−0.0015 (14)	0.0029 (16)	−0.0005 (14)
C7	0.034 (2)	0.0133 (18)	0.037 (2)	−0.0050 (15)	0.0053 (17)	0.0005 (16)
C8	0.040 (2)	0.0197 (19)	0.056 (2)	0.0112 (16)	−0.0004 (18)	0.0031 (16)
C9	0.035 (2)	0.0127 (17)	0.0329 (19)	−0.0090 (15)	0.0039 (16)	−0.0007 (14)
C10	0.041 (2)	0.0234 (18)	0.049 (2)	0.0059 (17)	−0.0031 (17)	0.0051 (17)

O1—C7	1.330 (3)	C3—C4	1.379 (4)
O1—C8	1.455 (3)	C3—C7	1.512 (4)
O2—C7	1.195 (3)	C4—C5	1.376 (4)
O3—C9	1.333 (3)	C4—H4A	0.9500
O3—C10	1.450 (3)	C5—C6	1.403 (4)
O4—C9	1.216 (3)	C5—H5A	0.9500
N1—C1	1.365 (4)	C6—C9	1.489 (4)
N1—H1A	0.92 (4)	C8—H8A	0.9800
N1—H1B	0.94 (3)	C8—H8B	0.9800
C1—C6	1.398 (4)	C8—H8C	0.9800
C1—C2	1.418 (4)	C10—H10A	0.9800
C2—C3	1.368 (4)	C10—H10B	0.9800
C2—H2A	0.9500	C10—H10C	0.9800
C7—O1—C8	115.6 (2)	C1—C6—C9	120.5 (3)
C9—O3—C10	115.7 (2)	C5—C6—C9	119.9 (3)
C1—N1—H1A	111 (2)	O2—C7—O1	123.8 (3)
C1—N1—H1B	120 (2)	O2—C7—C3	124.3 (3)
H1A—N1—H1B	122 (3)	O1—C7—C3	111.9 (3)
N1—C1—C6	123.9 (3)	O1—C8—H8A	109.5
N1—C1—C2	118.4 (3)	O1—C8—H8B	109.5
C6—C1—C2	117.7 (3)	H8A—C8—H8B	109.5
C3—C2—C1	121.0 (3)	O1—C8—H8C	109.5
C3—C2—H2A	119.5	H8A—C8—H8C	109.5
C1—C2—H2A	119.5	H8B—C8—H8C	109.5
C2—C3—C4	121.3 (3)	O4—C9—O3	122.3 (3)
C2—C3—C7	117.0 (3)	O4—C9—C6	124.8 (3)
C4—C3—C7	121.7 (3)	O3—C9—C6	112.9 (3)
C5—C4—C3	118.7 (3)	O3—C10—H10A	109.5
C5—C4—H4A	120.6	O3—C10—H10B	109.5
C3—C4—H4A	120.6	H10A—C10—H10B	109.5
C4—C5—C6	121.6 (3)	O3—C10—H10C	109.5
C4—C5—H5A	119.2	H10A—C10—H10C	109.5
C6—C5—H5A	119.2	H10B—C10—H10C	109.5
C1—C6—C5	119.6 (3)
N1—C1—C2—C3	179.4 (3)	C8—O1—C7—O2	−2.7 (4)
C6—C1—C2—C3	0.4 (4)	C8—O1—C7—C3	177.5 (2)
C1—C2—C3—C4	−0.1 (4)	C2—C3—C7—O2	−1.7 (4)
C1—C2—C3—C7	177.6 (3)	C4—C3—C7—O2	176.1 (3)
C2—C3—C4—C5	−0.3 (4)	C2—C3—C7—O1	178.1 (2)
C7—C3—C4—C5	−178.0 (3)	C4—C3—C7—O1	−4.1 (4)
C3—C4—C5—C6	0.5 (4)	C10—O3—C9—O4	2.2 (4)
N1—C1—C6—C5	−179.2 (3)	C10—O3—C9—C6	−178.6 (2)
C2—C1—C6—C5	−0.1 (4)	C1—C6—C9—O4	4.7 (4)
N1—C1—C6—C9	1.2 (5)	C5—C6—C9—O4	−175.0 (3)
C2—C1—C6—C9	−179.8 (3)	C1—C6—C9—O3	−174.5 (3)
C4—C5—C6—C1	−0.3 (4)	C5—C6—C9—O3	5.8 (4)
C4—C5—C6—C9	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.92 (4)	2.01 (4)	2.717 (4)	133 (3)
N1—H1B···O2i	0.95 (4)	2.14 (3)	3.016 (4)	153 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.92 (4)	2.01 (4)	2.717 (4)	133 (3)
N1—H1B⋯O2i	0.95 (4)	2.14 (3)	3.016 (4)	153 (3)

Symmetry code: (i) .