2-Amino-terephthalic acid N,N-dimethyl-formamide disolvate.

The asymmetric unit of the title structure, C(8)H(7)NO(4)·2C(3)H(7)NO, contains one 2-amino-terephthalic acid and two N,N-dimethyl-formamide mol-ecules. Strong O-H⋯O hydrogen bonds between the acidic carb-oxy H atoms of 2-am-ino-terephthalic acid and the O atoms of both solvent mol-ecules form linear 1:2 complex units. One H atom of the amine group is involved in intra-molecular N-H⋯O hydrogen bonding, whereas the second one takes part in an inter-molecular N-H⋯O connection. Furthermore, the crystal is stabilized by weak C-H⋯O hydrogen bonds.

Related literature

For the structure of 2-amino­terephthalic acid dimethyl ester, see: Brüning et al. (2009 ▶). For the use of this carb­oxy­lic acid in the synthesis of porous structures, see: Bauer et al. (2008 ▶). For a co-crystal of 2-amino­terephthalic acid, see: Xiao et al. (2011 ▶).

Experimental

Crystal data

C8H7NO4·2C3H7NO

M = 327.34

Monoclinic,

a = 7.8393 (2) Å

b = 9.7462 (2) Å

c = 10.9147 (2) Å

β = 103.251 (1)°

V = 811.72 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 153 K

0.58 × 0.51 × 0.37 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.941, T max = 0.962

19574 measured reflections

2260 independent reflections

2157 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.092

S = 1.05

2260 reflections

223 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-NT (Bruker, 2007 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031431/fy2048sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031431/fy2048Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031431/fy2048Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812031431/fy2048Isup4.cml

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

C8H7NO4·2C3H7NO	F(000) = 348
Mr = 327.34	Dx = 1.339 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 9996 reflections
a = 7.8393 (2) Å	θ = 2.8–33.3°
b = 9.7462 (2) Å	µ = 0.11 mm−1
c = 10.9147 (2) Å	T = 153 K
β = 103.251 (1)°	Irregular, colourless
V = 811.72 (3) Å3	0.58 × 0.51 × 0.37 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2260 independent reflections
Radiation source: fine-focus sealed tube	2157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 29.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.941, Tmax = 0.962	k = −13→13
19574 measured reflections	l = −15→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.133P] where P = (Fo2 + 2Fc2)/3
2260 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.21 e Å−3
4 restraints	Δρmin = −0.17 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	0.25655 (18)	0.55493 (13)	0.50464 (13)	0.0305 (3)
O2	0.43465 (18)	0.57438 (14)	0.69541 (12)	0.0288 (3)
H2	0.3800	0.6484	0.6961	0.043*
O3	0.55866 (19)	−0.12115 (13)	0.49500 (12)	0.0293 (3)
H3	0.6119	−0.1963	0.4984	0.044*
O4	0.72462 (18)	−0.09748 (14)	0.69012 (12)	0.0289 (3)
N1	0.2490 (2)	0.31517 (16)	0.38262 (14)	0.0282 (3)
H1A	0.214 (3)	0.3941 (14)	0.385 (3)	0.035 (6)*
H1B	0.228 (4)	0.259 (3)	0.323 (2)	0.057 (9)*
C1	0.4280 (2)	0.36183 (18)	0.59253 (14)	0.0197 (3)
C2	0.3678 (2)	0.27585 (15)	0.48708 (14)	0.0188 (3)
C3	0.4335 (2)	0.14046 (16)	0.49115 (14)	0.0197 (3)
H3A	0.3961	0.0818	0.4206	0.024*
C4	0.5515 (2)	0.09231 (17)	0.59659 (14)	0.0196 (3)
C5	0.6101 (2)	0.17684 (18)	0.70191 (15)	0.0227 (3)
H5	0.6911	0.1433	0.7742	0.027*
C6	0.5478 (2)	0.30979 (17)	0.69856 (15)	0.0224 (3)
H6	0.5868	0.3675	0.7696	0.027*
C7	0.3648 (2)	0.50511 (16)	0.59147 (16)	0.0215 (3)
C8	0.6191 (2)	−0.05168 (17)	0.59927 (15)	0.0217 (3)
O1A	0.7117 (2)	0.64886 (15)	0.48597 (13)	0.0359 (3)
N1A	0.8832 (2)	0.48490 (17)	0.59960 (15)	0.0275 (3)
C1A	0.8124 (3)	0.60873 (19)	0.58446 (17)	0.0288 (4)
H1AA	0.8403	0.6708	0.6532	0.035*
C2A	0.9926 (3)	0.4434 (2)	0.7207 (2)	0.0346 (4)
H2A1	0.9982	0.5183	0.7815	0.052*
H2A2	1.1110	0.4224	0.7109	0.052*
H2A3	0.9421	0.3618	0.7512	0.052*
C3A	0.8513 (3)	0.3853 (2)	0.49843 (19)	0.0342 (4)
H3A1	0.7960	0.4309	0.4192	0.051*
H3A2	0.7736	0.3132	0.5166	0.051*
H3A3	0.9628	0.3446	0.4910	0.051*
O1B	0.2883 (2)	0.80983 (15)	0.70391 (14)	0.0362 (3)
N1B	0.10043 (19)	0.96613 (16)	0.59172 (15)	0.0258 (3)
C1B	0.1865 (2)	0.84831 (19)	0.60504 (18)	0.0284 (4)
H1BA	0.1694	0.7890	0.5342	0.034*
C2B	0.1191 (3)	1.0619 (2)	0.6961 (2)	0.0347 (4)
H2B1	0.1608	1.0127	0.7756	0.052*
H2B2	0.0053	1.1041	0.6951	0.052*
H2B3	0.2037	1.1334	0.6878	0.052*
C3B	−0.0088 (3)	1.0077 (2)	0.47142 (19)	0.0334 (4)
H3B1	0.0445	1.0868	0.4392	0.050*
H3B2	−0.1254	1.0328	0.4823	0.050*
H3B3	−0.0190	0.9315	0.4115	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0356 (7)	0.0217 (6)	0.0287 (7)	0.0068 (5)	−0.0045 (5)	−0.0052 (5)
O2	0.0347 (7)	0.0224 (6)	0.0248 (6)	0.0032 (5)	−0.0028 (5)	−0.0082 (5)
O3	0.0399 (7)	0.0205 (6)	0.0232 (6)	0.0087 (5)	−0.0018 (5)	−0.0003 (5)
O4	0.0360 (7)	0.0214 (6)	0.0246 (6)	0.0041 (5)	−0.0028 (5)	0.0039 (5)
N1	0.0353 (8)	0.0219 (6)	0.0209 (6)	0.0074 (6)	−0.0069 (5)	−0.0031 (5)
C1	0.0210 (7)	0.0202 (8)	0.0167 (6)	−0.0003 (5)	0.0018 (5)	−0.0022 (5)
C2	0.0206 (7)	0.0179 (7)	0.0167 (6)	0.0009 (5)	0.0019 (5)	−0.0005 (5)
C3	0.0224 (7)	0.0186 (7)	0.0161 (6)	0.0004 (5)	0.0002 (5)	−0.0003 (5)
C4	0.0229 (7)	0.0167 (7)	0.0185 (7)	0.0016 (5)	0.0032 (6)	0.0020 (5)
C5	0.0247 (7)	0.0239 (8)	0.0171 (6)	0.0015 (6)	−0.0002 (6)	0.0011 (6)
C6	0.0246 (7)	0.0236 (7)	0.0177 (7)	−0.0001 (6)	0.0023 (6)	−0.0029 (6)
C7	0.0237 (7)	0.0181 (7)	0.0222 (7)	−0.0007 (6)	0.0041 (6)	−0.0045 (6)
C8	0.0244 (8)	0.0207 (8)	0.0191 (7)	−0.0002 (6)	0.0031 (6)	0.0033 (6)
O1A	0.0498 (9)	0.0278 (7)	0.0260 (7)	0.0144 (6)	−0.0001 (6)	−0.0016 (5)
N1A	0.0289 (8)	0.0272 (8)	0.0258 (7)	0.0055 (6)	0.0050 (6)	0.0009 (6)
C1A	0.0348 (9)	0.0243 (8)	0.0262 (8)	0.0052 (7)	0.0046 (7)	−0.0012 (6)
C2A	0.0313 (9)	0.0363 (10)	0.0340 (10)	0.0089 (8)	0.0030 (8)	0.0063 (8)
C3A	0.0427 (11)	0.0266 (9)	0.0341 (10)	0.0100 (8)	0.0104 (8)	−0.0024 (7)
O1B	0.0456 (8)	0.0271 (7)	0.0320 (7)	0.0090 (6)	0.0007 (6)	−0.0055 (5)
N1B	0.0258 (7)	0.0237 (7)	0.0268 (7)	0.0012 (6)	0.0036 (6)	−0.0039 (6)
C1B	0.0334 (9)	0.0226 (8)	0.0288 (9)	−0.0008 (7)	0.0065 (7)	−0.0060 (6)
C2B	0.0369 (10)	0.0308 (9)	0.0333 (9)	0.0062 (7)	0.0015 (8)	−0.0121 (8)
C3B	0.0313 (9)	0.0395 (11)	0.0276 (9)	0.0061 (8)	0.0031 (7)	−0.0006 (8)

O1—C7	1.219 (2)	N1A—C1A	1.323 (2)
O2—C7	1.326 (2)	N1A—C3A	1.448 (3)
O2—H2	0.8400	N1A—C2A	1.458 (2)
O3—C8	1.316 (2)	C1A—H1AA	0.9500
O3—H3	0.8400	C2A—H2A1	0.9800
O4—C8	1.221 (2)	C2A—H2A2	0.9800
N1—C2	1.352 (2)	C2A—H2A3	0.9800
N1—H1A	0.820 (10)	C3A—H3A1	0.9800
N1—H1B	0.837 (10)	C3A—H3A2	0.9800
C1—C6	1.407 (2)	C3A—H3A3	0.9800
C1—C2	1.414 (2)	O1B—C1B	1.244 (2)
C1—C7	1.481 (2)	N1B—C1B	1.323 (2)
C2—C3	1.413 (2)	N1B—C3B	1.451 (3)
C3—C4	1.383 (2)	N1B—C2B	1.454 (2)
C3—H3A	0.9500	C1B—H1BA	0.9500
C4—C5	1.403 (2)	C2B—H2B1	0.9800
C4—C8	1.498 (2)	C2B—H2B2	0.9800
C5—C6	1.382 (2)	C2B—H2B3	0.9800
C5—H5	0.9500	C3B—H3B1	0.9800
C6—H6	0.9500	C3B—H3B2	0.9800
O1A—C1A	1.242 (2)	C3B—H3B3	0.9800
C7—O2—H2	109.5	O1A—C1A—H1AA	117.9
C8—O3—H3	109.5	N1A—C1A—H1AA	117.9
C2—N1—H1A	114 (2)	N1A—C2A—H2A1	109.5
C2—N1—H1B	116 (2)	N1A—C2A—H2A2	109.5
H1A—N1—H1B	130 (3)	H2A1—C2A—H2A2	109.5
C6—C1—C2	119.41 (14)	N1A—C2A—H2A3	109.5
C6—C1—C7	120.36 (14)	H2A1—C2A—H2A3	109.5
C2—C1—C7	120.23 (14)	H2A2—C2A—H2A3	109.5
N1—C2—C3	117.82 (14)	N1A—C3A—H3A1	109.5
N1—C2—C1	123.73 (14)	N1A—C3A—H3A2	109.5
C3—C2—C1	118.44 (14)	H3A1—C3A—H3A2	109.5
C4—C3—C2	120.82 (14)	N1A—C3A—H3A3	109.5
C4—C3—H3A	119.6	H3A1—C3A—H3A3	109.5
C2—C3—H3A	119.6	H3A2—C3A—H3A3	109.5
C3—C4—C5	120.90 (15)	C1B—N1B—C3B	121.47 (16)
C3—C4—C8	120.03 (14)	C1B—N1B—C2B	120.93 (16)
C5—C4—C8	119.07 (14)	C3B—N1B—C2B	117.53 (15)
C6—C5—C4	118.77 (14)	O1B—C1B—N1B	124.52 (17)
C6—C5—H5	120.6	O1B—C1B—H1BA	117.7
C4—C5—H5	120.6	N1B—C1B—H1BA	117.7
C5—C6—C1	121.65 (15)	N1B—C2B—H2B1	109.5
C5—C6—H6	119.2	N1B—C2B—H2B2	109.5
C1—C6—H6	119.2	H2B1—C2B—H2B2	109.5
O1—C7—O2	122.68 (15)	N1B—C2B—H2B3	109.5
O1—C7—C1	123.64 (14)	H2B1—C2B—H2B3	109.5
O2—C7—C1	113.67 (15)	H2B2—C2B—H2B3	109.5
O4—C8—O3	123.85 (16)	N1B—C3B—H3B1	109.5
O4—C8—C4	121.95 (15)	N1B—C3B—H3B2	109.5
O3—C8—C4	114.17 (14)	H3B1—C3B—H3B2	109.5
C1A—N1A—C3A	121.45 (17)	N1B—C3B—H3B3	109.5
C1A—N1A—C2A	120.58 (16)	H3B1—C3B—H3B3	109.5
C3A—N1A—C2A	117.94 (16)	H3B2—C3B—H3B3	109.5
O1A—C1A—N1A	124.11 (17)
C6—C1—C2—N1	177.95 (16)	C6—C1—C7—O1	−177.30 (17)
C7—C1—C2—N1	−1.7 (2)	C2—C1—C7—O1	2.4 (3)
C6—C1—C2—C3	−1.3 (2)	C6—C1—C7—O2	1.5 (2)
C7—C1—C2—C3	179.05 (15)	C2—C1—C7—O2	−178.78 (15)
N1—C2—C3—C4	−178.14 (15)	C3—C4—C8—O4	179.29 (16)
C1—C2—C3—C4	1.1 (2)	C5—C4—C8—O4	−0.5 (2)
C2—C3—C4—C5	−0.5 (2)	C3—C4—C8—O3	1.0 (2)
C2—C3—C4—C8	179.80 (15)	C5—C4—C8—O3	−178.70 (15)
C3—C4—C5—C6	−0.1 (2)	C3A—N1A—C1A—O1A	1.7 (3)
C8—C4—C5—C6	179.68 (16)	C2A—N1A—C1A—O1A	−176.6 (2)
C4—C5—C6—C1	−0.1 (3)	C3B—N1B—C1B—O1B	176.51 (18)
C2—C1—C6—C5	0.8 (2)	C2B—N1B—C1B—O1B	−0.4 (3)
C7—C1—C6—C5	−179.54 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.81 (3)	2.03 (3)	2.685 (2)	138 (3)
N1—H1B···O4i	0.84 (2)	2.14 (3)	2.960 (2)	169 (3)
O3—H3···O1Aii	0.84	1.72	2.5549 (19)	173
O2—H2···O1B	0.84	1.74	2.577 (2)	174
C1A—H1AA···O4iii	0.95	2.50	3.219 (2)	133
C1B—H1BA···O1	0.95	2.42	3.155 (2)	134
C3—H3A···O4i	0.95	2.57	3.344 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.81 (3)	2.03 (3)	2.685 (2)	138 (3)
N1—H1B⋯O4i	0.84 (2)	2.14 (3)	2.960 (2)	169 (3)
O3—H3⋯O1A ii	0.84	1.72	2.5549 (19)	173
O2—H2⋯O1B	0.84	1.74	2.577 (2)	174
C1A—H1AA⋯O4iii	0.95	2.50	3.219 (2)	133
C1B—H1BA⋯O1	0.95	2.42	3.155 (2)	134
C3—H3A⋯O4i	0.95	2.57	3.344 (2)	139

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