2-Amino-6-methyl-1,3-benzothia-zole-octa-nedioic acid (2/1).

Cocrystallization of 2-amino-6-methy-1,3-benzothia-zole with octa-nedioic acid in a mixed methanol-water medium afforded the title 2:1 cocrystal, 2C(8)H(8)N(2)S·C(8)H(14)O(4). The octa-nedioic acid mol-ecule is located on an inversion centre. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds connect the components into a three-dimensional network.

Related literature

For mol­ecular self-assembly and its application in crystal engineering, see: Yang et al. (2007 ▶); Hunter (1993 ▶); Zhao et al. (2007 ▶). For the structures and properties of metal complexes and co-crystals with amino­benzothia­zole and its derivatives, see: Shi et al. (2009 ▶); Lynch et al. (1999 ▶); Chen et al. (2008 ▶); Zhang et al. (2009 ▶). For the structure and performance of octa­nedioic acid-based metal complexes and co-crystals, see: Geraghty et al. (1999 ▶); McCann et al. (1995 ▶); Peral et al. (2001 ▶).

Experimental

Crystal data

2C8H8N2S·C8H14O4

M = 502.64

Monoclinic,

a = 12.4372 (12) Å

b = 7.9165 (8) Å

c = 16.6061 (12) Å

β = 127.992 (5)°

V = 1288.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.958

6745 measured reflections

2271 independent reflections

1767 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.098

S = 1.05

2271 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042652/bt5102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042652/bt5102Isup2.hkl

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

2C8H8N2S·C8H14O4	F(000) = 532
Mr = 502.64	Dx = 1.295 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.4372 (12) Å	Cell parameters from 2130 reflections
b = 7.9165 (8) Å	θ = 2.5–24.4°
c = 16.6061 (12) Å	µ = 0.24 mm−1
β = 127.992 (5)°	T = 293 K
V = 1288.6 (2) Å3	Block, colourless
Z = 2	0.25 × 0.20 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	2271 independent reflections
Radiation source: fine-focus sealed tube	1767 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.942, Tmax = 0.958	k = −7→9
6745 measured reflections	l = −19→19

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.215P] where P = (Fo2 + 2Fc2)/3
2271 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 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
S1	0.27303 (5)	−0.11551 (6)	1.15536 (3)	0.06084 (19)
O1	0.41522 (14)	0.48915 (16)	1.10448 (9)	0.0707 (4)
O2	0.24755 (15)	0.39416 (17)	0.95120 (9)	0.0743 (4)
H2	0.2495	0.3168	0.9849	0.111*
N1	0.23024 (15)	0.12817 (17)	1.03421 (11)	0.0561 (4)
N2	0.40617 (17)	0.1802 (2)	1.20575 (12)	0.0760 (5)
H2A	0.4222	0.2778	1.1924	0.091*
H2B	0.4541	0.1450	1.2679	0.091*
C1	0.13613 (17)	0.0017 (2)	0.97271 (13)	0.0517 (4)
C2	0.14393 (17)	−0.1411 (2)	1.02435 (13)	0.0534 (4)
C3	0.0586 (2)	−0.2780 (3)	0.97316 (14)	0.0700 (6)
H3	0.0656	−0.3730	1.0090	0.084*
C4	−0.0376 (2)	−0.2717 (3)	0.86769 (15)	0.0711 (6)
C5	−0.0446 (2)	−0.1297 (3)	0.81731 (15)	0.0716 (6)
H5	−0.1090	−0.1260	0.7465	0.086*
C6	0.03990 (19)	0.0074 (3)	0.86719 (13)	0.0656 (5)
H6	0.0325	0.1020	0.8308	0.079*
C7	0.30726 (18)	0.0837 (2)	1.13027 (13)	0.0541 (4)
C8	−0.1328 (3)	−0.4193 (4)	0.81008 (19)	0.1066 (9)
H8A	−0.1898	−0.3967	0.7381	0.160*
H8B	−0.1888	−0.4354	0.8311	0.160*
H8C	−0.0803	−0.5196	0.8246	0.160*
C9	0.33968 (18)	0.5053 (2)	1.01209 (13)	0.0537 (4)
C10	0.34445 (19)	0.6517 (2)	0.95779 (13)	0.0570 (5)
H10A	0.2554	0.7052	0.9163	0.068*
H10B	0.3616	0.6092	0.9118	0.068*
C11	0.45049 (18)	0.7847 (2)	1.02578 (12)	0.0541 (4)
H11A	0.5402	0.7330	1.0659	0.065*
H11B	0.4351	0.8265	1.0728	0.065*
C12	0.44826 (18)	0.9325 (2)	0.96670 (13)	0.0564 (4)
H12A	0.4649	0.8906	0.9204	0.068*
H12B	0.3580	0.9825	0.9257	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.0674 (3)	0.0618 (3)	0.0453 (3)	−0.0065 (2)	0.0307 (2)	0.0036 (2)
O1	0.0878 (9)	0.0557 (8)	0.0427 (7)	−0.0119 (7)	0.0270 (7)	0.0017 (6)
O2	0.0888 (10)	0.0590 (9)	0.0466 (7)	−0.0179 (7)	0.0274 (7)	0.0011 (6)
N1	0.0597 (9)	0.0503 (9)	0.0469 (8)	0.0005 (7)	0.0272 (7)	0.0031 (7)
N2	0.0856 (12)	0.0609 (10)	0.0485 (9)	−0.0145 (9)	0.0246 (9)	−0.0005 (8)
C1	0.0489 (9)	0.0540 (10)	0.0480 (9)	0.0032 (8)	0.0276 (8)	0.0002 (8)
C2	0.0515 (10)	0.0613 (11)	0.0464 (9)	−0.0034 (8)	0.0296 (8)	0.0004 (8)
C3	0.0740 (13)	0.0726 (14)	0.0621 (12)	−0.0200 (11)	0.0413 (11)	−0.0048 (10)
C4	0.0610 (12)	0.0830 (15)	0.0565 (11)	−0.0164 (11)	0.0296 (10)	−0.0111 (11)
C5	0.0592 (12)	0.0876 (16)	0.0461 (10)	−0.0005 (11)	0.0215 (9)	−0.0039 (11)
C6	0.0621 (11)	0.0698 (13)	0.0470 (10)	0.0057 (10)	0.0245 (9)	0.0068 (9)
C7	0.0588 (10)	0.0519 (10)	0.0460 (9)	0.0016 (8)	0.0294 (9)	0.0009 (8)
C8	0.0974 (18)	0.117 (2)	0.0769 (16)	−0.0487 (16)	0.0392 (14)	−0.0237 (15)
C9	0.0618 (11)	0.0464 (10)	0.0449 (10)	0.0025 (8)	0.0288 (9)	0.0002 (8)
C10	0.0641 (11)	0.0534 (10)	0.0465 (9)	0.0020 (9)	0.0304 (9)	0.0046 (8)
C11	0.0611 (11)	0.0489 (10)	0.0479 (9)	0.0039 (8)	0.0313 (9)	0.0055 (8)
C12	0.0618 (11)	0.0547 (10)	0.0475 (9)	0.0039 (8)	0.0310 (9)	0.0085 (8)

S1—C2	1.7469 (18)	C5—C6	1.377 (3)
S1—C7	1.7491 (19)	C5—H5	0.9300
O1—C9	1.2159 (19)	C6—H6	0.9300
O2—C9	1.297 (2)	C8—H8A	0.9600
O2—H2	0.8200	C8—H8B	0.9600
N1—C7	1.306 (2)	C8—H8C	0.9600
N1—C1	1.394 (2)	C9—C10	1.492 (2)
N2—C7	1.331 (2)	C10—C11	1.513 (2)
N2—H2A	0.8599	C10—H10A	0.9700
N2—H2B	0.8601	C10—H10B	0.9700
C1—C2	1.386 (2)	C11—C12	1.516 (2)
C1—C6	1.387 (2)	C11—H11A	0.9700
C2—C3	1.383 (3)	C11—H11B	0.9700
C3—C4	1.386 (3)	C12—C12i	1.507 (4)
C3—H3	0.9300	C12—H12A	0.9700
C4—C5	1.371 (3)	C12—H12B	0.9700
C4—C8	1.513 (3)
C2—S1—C7	88.84 (8)	C4—C8—H8A	109.5
C9—O2—H2	109.5	C4—C8—H8B	109.5
C7—N1—C1	110.78 (15)	H8A—C8—H8B	109.5
C7—N2—H2A	120.0	C4—C8—H8C	109.5
C7—N2—H2B	120.0	H8A—C8—H8C	109.5
H2A—N2—H2B	120.0	H8B—C8—H8C	109.5
C2—C1—C6	119.08 (17)	O1—C9—O2	122.54 (16)
C2—C1—N1	115.16 (15)	O1—C9—C10	123.85 (16)
C6—C1—N1	125.76 (17)	O2—C9—C10	113.60 (15)
C3—C2—C1	121.59 (17)	C9—C10—C11	115.48 (14)
C3—C2—S1	128.73 (15)	C9—C10—H10A	108.4
C1—C2—S1	109.67 (13)	C11—C10—H10A	108.4
C2—C3—C4	119.16 (19)	C9—C10—H10B	108.4
C2—C3—H3	120.4	C11—C10—H10B	108.4
C4—C3—H3	120.4	H10A—C10—H10B	107.5
C5—C4—C3	118.79 (19)	C10—C11—C12	113.19 (14)
C5—C4—C8	121.09 (19)	C10—C11—H11A	108.9
C3—C4—C8	120.1 (2)	C12—C11—H11A	108.9
C4—C5—C6	122.73 (18)	C10—C11—H11B	108.9
C4—C5—H5	118.6	C12—C11—H11B	108.9
C6—C5—H5	118.6	H11A—C11—H11B	107.8
C5—C6—C1	118.65 (19)	C12i—C12—C11	113.92 (17)
C5—C6—H6	120.7	C12i—C12—H12A	108.8
C1—C6—H6	120.7	C11—C12—H12A	108.8
N1—C7—N2	123.60 (17)	C12i—C12—H12B	108.8
N1—C7—S1	115.54 (13)	C11—C12—H12B	108.8
N2—C7—S1	120.86 (14)	H12A—C12—H12B	107.7
C7—N1—C1—C2	−0.4 (2)	C8—C4—C5—C6	179.7 (2)
C7—N1—C1—C6	−179.52 (17)	C4—C5—C6—C1	0.1 (3)
C6—C1—C2—C3	0.3 (3)	C2—C1—C6—C5	−0.2 (3)
N1—C1—C2—C3	−178.90 (17)	N1—C1—C6—C5	178.93 (18)
C6—C1—C2—S1	179.83 (14)	C1—N1—C7—N2	179.78 (17)
N1—C1—C2—S1	0.64 (19)	C1—N1—C7—S1	0.0 (2)
C7—S1—C2—C3	178.97 (19)	C2—S1—C7—N1	0.34 (15)
C7—S1—C2—C1	−0.53 (13)	C2—S1—C7—N2	−179.49 (17)
C1—C2—C3—C4	−0.4 (3)	O1—C9—C10—C11	−0.7 (3)
S1—C2—C3—C4	−179.81 (16)	O2—C9—C10—C11	−179.99 (16)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	−178.51 (16)
C2—C3—C4—C8	−179.5 (2)	C10—C11—C12—C12i	179.07 (19)
C3—C4—C5—C6	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.79	2.5973 (19)	169
N2—H2B···O1ii	0.86	2.10	2.922 (2)	159
N2—H2A···O1	0.86	2.19	3.009 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.79	2.5973 (19)	169
N2—H2B⋯O1i	0.86	2.10	2.922 (2)	159
N2—H2A⋯O1	0.86	2.19	3.009 (2)	160

Symmetry code: (i) .