Pyromellitic acid-sarcosine (1/2).

The title compound, C(10)H(6)O(8)·2C(3)H(7)NO(2), crystallizes as an adduct with the acid and amino acid mol-ecules in their neutral forms. The asymmetric unit contains one half of a centrosymmetric pyromellitic acid mol-ecule and one sarcosine mol-ecule. The sarcosine has the amine group protonated and the carboxyl group deprotonated, as is usual for amino acids (zwitterionic form). The pyromellitic acid mol-ecules retain the four carboxyl H atoms with the carboxyl groups rotated out of the ring plane [O-C-C-C torsion angles = 24.1 (3) and 61.6 (2)°]. There is a three-dimensional hydrogen-bond network linking the mol-ecules.

Related literature

For related compounds, see: Yaghi et al. (1997 ▶); Arora & Pedireddi (2003 ▶); Rochon & Massarweh (2001 ▶); Kumagai et al. (2003 ▶).

Experimental

Crystal data

C10H6O8·2C3H7NO2

M = 432.34

Monoclinic,

a = 8.8894 (3) Å

b = 5.4118 (2) Å

c = 20.2205 (7) Å

β = 104.388 (2)°

V = 942.25 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 (2) K

0.47 × 0.10 × 0.07 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.915, T max = 0.998

16656 measured reflections

2351 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.01

2351 reflections

166 parameters

Only H-atom coordinates refined

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus (Bruker, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009045/dn2326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009045/dn2326Isup2.hkl

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

C10H6O8·2C3H7NO2	F000 = 452
Mr = 432.34	Dx = 1.524 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2870 reflections
a = 8.8894 (3) Å	θ = 2.4–23.7º
b = 5.4118 (2) Å	µ = 0.13 mm−1
c = 20.2205 (7) Å	T = 293 (2) K
β = 104.388 (2)º	Prism, colourless
V = 942.25 (6) Å3	0.47 × 0.10 × 0.07 mm
Z = 2

Bruker APEX CCD area-detector diffractometer	2351 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 293(2) K	θmax = 28.4º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −11→11
Tmin = 0.915, Tmax = 0.998	k = −7→7
16656 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	Only H-atom coordinates refined
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.056P)2 + 0.2509P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2351 reflections	Δρmax = 0.25 e Å−3
166 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.19992 (15)	0.1100 (3)	0.89313 (8)	0.0531 (4)
O2	0.43230 (15)	−0.0346 (2)	0.88997 (7)	0.0415 (4)
H2	0.389 (3)	−0.163 (4)	0.8612 (11)	0.050*
C1	0.33933 (19)	0.1205 (3)	0.90904 (8)	0.0291 (4)
C2	0.42466 (17)	0.3192 (3)	0.95451 (8)	0.0236 (3)
C3	0.57683 (17)	0.3865 (3)	0.95565 (8)	0.0239 (3)
C4	0.65079 (18)	0.5655 (3)	1.00139 (8)	0.0256 (3)
H1	0.758 (2)	0.621 (3)	1.0018 (9)	0.031*
C5	0.66506 (19)	0.2833 (3)	0.90749 (8)	0.0284 (4)
O4	0.78636 (14)	0.1742 (3)	0.92796 (7)	0.0418 (4)
O3	0.61224 (16)	0.3342 (3)	0.84210 (6)	0.0382 (3)
H3	0.515 (2)	0.430 (4)	0.8318 (11)	0.046*
O5	0.35723 (14)	0.5924 (2)	0.81422 (6)	0.0377 (3)
O6	0.12981 (14)	0.7404 (2)	0.75521 (6)	0.0365 (3)
C6	0.23381 (18)	0.5845 (3)	0.76612 (8)	0.0261 (4)
C7	0.21727 (19)	0.3602 (3)	0.71983 (9)	0.0284 (4)
H7A	0.205 (2)	0.202 (4)	0.7448 (9)	0.034*
H7B	0.310 (2)	0.343 (3)	0.7009 (9)	0.034*
N1	0.07624 (17)	0.3848 (3)	0.66375 (8)	0.0283 (3)
H1A	−0.004 (2)	0.404 (4)	0.6805 (10)	0.034*
H1B	0.087 (2)	0.516 (4)	0.6393 (10)	0.034*
C8	0.0406 (3)	0.1733 (4)	0.61676 (12)	0.0437 (5)
H8A	−0.047 (3)	0.212 (4)	0.5816 (12)	0.052*
H8B	0.123 (3)	0.159 (4)	0.5931 (11)	0.052*
H8C	0.033 (3)	0.037 (5)	0.6395 (12)	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0296 (7)	0.0604 (10)	0.0672 (10)	−0.0132 (6)	0.0080 (6)	−0.0350 (8)
O2	0.0364 (7)	0.0329 (7)	0.0517 (8)	−0.0029 (6)	0.0042 (6)	−0.0215 (6)
C1	0.0313 (9)	0.0282 (9)	0.0271 (8)	−0.0057 (7)	0.0061 (7)	−0.0040 (7)
C2	0.0250 (8)	0.0231 (8)	0.0213 (8)	−0.0009 (6)	0.0030 (6)	−0.0020 (6)
C3	0.0240 (7)	0.0247 (8)	0.0227 (8)	0.0016 (6)	0.0054 (6)	−0.0013 (6)
C4	0.0227 (7)	0.0282 (9)	0.0255 (8)	−0.0026 (6)	0.0052 (6)	−0.0021 (7)
C5	0.0275 (8)	0.0283 (9)	0.0298 (9)	−0.0015 (7)	0.0079 (7)	−0.0059 (7)
O4	0.0333 (7)	0.0487 (8)	0.0437 (8)	0.0126 (6)	0.0105 (6)	−0.0056 (6)
O3	0.0410 (7)	0.0487 (8)	0.0271 (7)	0.0070 (6)	0.0128 (5)	−0.0032 (6)
O5	0.0416 (7)	0.0326 (7)	0.0321 (7)	0.0032 (6)	−0.0034 (5)	−0.0080 (5)
O6	0.0374 (7)	0.0330 (7)	0.0393 (7)	0.0073 (6)	0.0098 (6)	−0.0068 (6)
C6	0.0295 (8)	0.0253 (8)	0.0242 (8)	−0.0017 (7)	0.0079 (6)	−0.0009 (7)
C7	0.0292 (9)	0.0258 (9)	0.0274 (9)	0.0031 (7)	0.0019 (7)	−0.0028 (7)
N1	0.0255 (7)	0.0285 (8)	0.0292 (8)	0.0006 (6)	0.0036 (6)	−0.0038 (6)
C8	0.0486 (12)	0.0370 (11)	0.0390 (11)	0.0027 (10)	−0.0015 (10)	−0.0142 (9)

O1—C1	1.202 (2)	O5—C6	1.273 (2)
O2—C1	1.302 (2)	O6—C6	1.230 (2)
O2—H2	0.93 (2)	C6—C7	1.518 (2)
C1—C2	1.493 (2)	C7—N1	1.473 (2)
C2—C4i	1.390 (2)	C7—H7A	1.02 (2)
C2—C3	1.396 (2)	C7—H7B	0.995 (19)
C3—C4	1.387 (2)	N1—C8	1.471 (2)
C3—C5	1.502 (2)	N1—H1A	0.87 (2)
C4—C2i	1.390 (2)	N1—H1B	0.88 (2)
C4—H1	0.997 (18)	C8—H8A	0.94 (2)
C5—O4	1.209 (2)	C8—H8B	0.97 (2)
C5—O3	1.318 (2)	C8—H8C	0.88 (2)
O3—H3	0.98 (2)
C1—O2—H2	118.4 (14)	O5—C6—C7	115.53 (14)
O1—C1—O2	125.37 (16)	N1—C7—C6	109.64 (13)
O1—C1—C2	122.06 (16)	N1—C7—H7A	106.5 (11)
O2—C1—C2	112.57 (14)	C6—C7—H7A	112.0 (10)
C4i—C2—C3	119.49 (14)	N1—C7—H7B	109.9 (11)
C4i—C2—C1	117.78 (14)	C6—C7—H7B	110.5 (11)
C3—C2—C1	122.70 (14)	H7A—C7—H7B	108.2 (15)
C4—C3—C2	119.36 (14)	C8—N1—C7	115.63 (15)
C4—C3—C5	117.05 (14)	C8—N1—H1A	106.3 (13)
C2—C3—C5	123.53 (14)	C7—N1—H1A	109.5 (13)
C3—C4—C2i	121.14 (14)	C8—N1—H1B	107.4 (13)
C3—C4—H1	120.5 (10)	C7—N1—H1B	108.1 (13)
C2i—C4—H1	118.3 (11)	H1A—N1—H1B	109.8 (18)
O4—C5—O3	120.72 (15)	N1—C8—H8A	108.6 (14)
O4—C5—C3	121.66 (15)	N1—C8—H8B	108.0 (14)
O3—C5—C3	117.36 (14)	H8A—C8—H8B	103.5 (18)
C5—O3—H3	113.4 (12)	N1—C8—H8C	110.2 (16)
O6—C6—O5	125.48 (16)	H8A—C8—H8C	115 (2)
O6—C6—C7	118.98 (15)	H8B—C8—H8C	111 (2)
O1—C1—C2—C4i	24.1 (3)	C5—C3—C4—C2i	176.64 (15)
O2—C1—C2—C4i	−155.56 (15)	C4—C3—C5—O4	61.6 (2)
O1—C1—C2—C3	−157.90 (18)	C2—C3—C5—O4	−121.1 (2)
O2—C1—C2—C3	22.4 (2)	C4—C3—C5—O3	−112.73 (18)
C4i—C2—C3—C4	0.7 (3)	C2—C3—C5—O3	64.5 (2)
C1—C2—C3—C4	−177.23 (15)	O6—C6—C7—N1	4.9 (2)
C4i—C2—C3—C5	−176.47 (15)	O5—C6—C7—N1	−175.62 (15)
C1—C2—C3—C5	5.5 (3)	C6—C7—N1—C8	−176.75 (17)
C2—C3—C4—C2i	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ii	0.93 (2)	1.61 (2)	2.5216 (18)	166 (2)
O3—H3···O5	0.98 (2)	1.62 (2)	2.6026 (18)	179 (2)
N1—H1A···O6iii	0.87 (2)	2.11 (2)	2.854 (2)	143.4 (17)
N1—H1A···O1iv	0.87 (2)	2.28 (2)	2.7262 (19)	111.8 (15)
N1—H1B···O4v	0.88 (2)	2.15 (2)	2.917 (2)	145.5 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5i	0.93 (2)	1.61 (2)	2.5216 (18)	166 (2)
O3—H3⋯O5	0.98 (2)	1.62 (2)	2.6026 (18)	179 (2)
N1—H1A⋯O6ii	0.87 (2)	2.11 (2)	2.854 (2)	143.4 (17)
N1—H1A⋯O1iii	0.87 (2)	2.28 (2)	2.7262 (19)	111.8 (15)
N1—H1B⋯O4iv	0.88 (2)	2.15 (2)	2.917 (2)	145.5 (16)

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