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

Co-crystallization of 2-amino-6-methyl-1,3--benzothia-zole with deca-nedioic acid under hydro-thermal conditions afforded the title 2:1 co-crystal, 2C(8)H(8)N(2)S·C(10)H(18)O(4). The deca-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 two-dimensional wave-like layer structure extending parallel to (100).

Related literature

For mol­ecular self-assembly and crystal engineering, see: Sun & Cui (2008 ▶); Hunter (1993 ▶); Yang et al. (2005 ▶). For the solid structures and properties of metal complexes of amino­benzothia­zole and its derivatives, see: Lynch et al. (1998 ▶, 1999 ▶); Sun & Cui (2008 ▶); Popović et al. (2002 ▶); Antiñolo et al. (2007 ▶); Dong et al. (2002 ▶); Chen et al. (2008 ▶); Zhang et al. (2009 ▶). For the structures of deca­nedioic acid-based n class="Chemical">metal complexes and co-crystals, see: Xian et al. (2009 ▶); Braga et al. (2006 ▶); Aakeröy et al. (2007 ▶).

Experimental

Crystal data

2C8H8N2S·C10H18O4

M = 530.71

Monoclinic,

a = 5.3791 (5) Å

b = 21.822 (2) Å

c = 11.9431 (11) Å

β = 91.6660 (10)°

V = 1401.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.931, T max = 0.952

7545 measured reflections

2470 independent reflections

1822 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.05

2470 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809031857/bt5031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031857/bt5031Isup2.hkl

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

2C8H8N2S·C10H18O4	F(000) = 564
Mr = 530.71	Dx = 1.258 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.3791 (5) Å	Cell parameters from 1765 reflections
b = 21.822 (2) Å	θ = 2.5–22.8°
c = 11.9431 (11) Å	µ = 0.23 mm−1
β = 91.666 (1)°	T = 293 K
V = 1401.3 (2) Å3	Block, pale-yellow
Z = 2	0.32 × 0.24 × 0.22 mm

Bruker APEXII CCD area-detector diffractometer	2470 independent reflections
Radiation source: fine-focus sealed tube	1822 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.931, Tmax = 0.952	k = −25→21
7545 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.3107P] where P = (Fo2 + 2Fc2)/3
2470 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 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	0.47667 (11)	0.17050 (3)	0.20230 (5)	0.0647 (2)
O1	1.1513 (3)	0.27012 (7)	−0.03449 (11)	0.0595 (4)
H1	1.0456	0.2531	0.0026	0.089*
O2	1.2105 (3)	0.32343 (7)	0.12223 (12)	0.0662 (4)
N1	0.8009 (3)	0.21067 (7)	0.06387 (13)	0.0502 (4)
N2	0.8217 (3)	0.25824 (8)	0.23838 (14)	0.0628 (5)
H2A	0.9420	0.2815	0.2189	0.075*
H2B	0.7643	0.2610	0.3046	0.075*
C1	0.7248 (4)	0.21790 (9)	0.16608 (16)	0.0495 (5)
C2	0.4781 (4)	0.13827 (9)	0.06865 (17)	0.0536 (5)
C3	0.3269 (4)	0.09285 (10)	0.02272 (19)	0.0658 (6)
H3A	0.2024	0.0754	0.0648	0.079*
C4	0.3619 (4)	0.07353 (10)	−0.0861 (2)	0.0647 (6)
C5	0.5474 (4)	0.10135 (11)	−0.14663 (18)	0.0650 (6)
H5A	0.5703	0.0889	−0.2201	0.078*
C6	0.6984 (4)	0.14661 (10)	−0.10228 (17)	0.0599 (6)
H6A	0.8214	0.1643	−0.1449	0.072*
C7	0.6645 (4)	0.16541 (9)	0.00673 (16)	0.0488 (5)
C8	0.1999 (6)	0.02374 (13)	−0.1383 (2)	0.0920 (9)
H8A	0.0819	0.0101	−0.0850	0.138*
H8B	0.3023	−0.0101	−0.1597	0.138*
H8C	0.1130	0.0397	−0.2033	0.138*
C9	1.2624 (4)	0.31276 (9)	0.02632 (16)	0.0469 (5)
C10	1.4559 (4)	0.34752 (9)	−0.03539 (16)	0.0511 (5)
H10A	1.3758	0.3681	−0.0987	0.061*
H10B	1.5740	0.3185	−0.0648	0.061*
C11	1.5968 (4)	0.39443 (9)	0.03408 (16)	0.0509 (5)
H11A	1.6931	0.3735	0.0924	0.061*
H11B	1.4788	0.4210	0.0701	0.061*
C12	1.7698 (4)	0.43316 (9)	−0.03430 (17)	0.0517 (5)
H12A	1.8855	0.4064	−0.0713	0.062*
H12B	1.6726	0.4544	−0.0920	0.062*
C13	1.9159 (4)	0.47985 (9)	0.03387 (16)	0.0511 (5)
H13A	2.0164	0.4585	0.0901	0.061*
H13B	1.8000	0.5058	0.0727	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0678 (4)	0.0744 (4)	0.0529 (3)	−0.0197 (3)	0.0191 (3)	0.0042 (3)
O1	0.0673 (10)	0.0637 (9)	0.0484 (8)	−0.0271 (7)	0.0198 (7)	−0.0071 (7)
O2	0.0763 (11)	0.0750 (10)	0.0484 (8)	−0.0275 (8)	0.0207 (7)	−0.0107 (7)
N1	0.0517 (10)	0.0565 (10)	0.0428 (9)	−0.0120 (8)	0.0086 (7)	0.0036 (7)
N2	0.0740 (13)	0.0691 (12)	0.0460 (9)	−0.0193 (10)	0.0129 (9)	−0.0042 (9)
C1	0.0512 (12)	0.0513 (11)	0.0464 (11)	−0.0036 (9)	0.0074 (9)	0.0084 (9)
C2	0.0538 (12)	0.0549 (12)	0.0524 (11)	−0.0087 (10)	0.0061 (9)	0.0091 (10)
C3	0.0606 (14)	0.0675 (14)	0.0695 (14)	−0.0214 (12)	0.0070 (11)	0.0113 (12)
C4	0.0671 (15)	0.0618 (13)	0.0646 (14)	−0.0132 (12)	−0.0080 (11)	0.0024 (11)
C5	0.0712 (15)	0.0740 (15)	0.0497 (12)	−0.0096 (12)	−0.0002 (11)	−0.0010 (11)
C6	0.0615 (14)	0.0691 (14)	0.0495 (12)	−0.0136 (11)	0.0063 (10)	0.0034 (10)
C7	0.0482 (12)	0.0515 (11)	0.0465 (11)	−0.0050 (9)	0.0012 (9)	0.0087 (9)
C8	0.097 (2)	0.0889 (19)	0.0893 (18)	−0.0331 (17)	−0.0044 (16)	−0.0102 (16)
C9	0.0476 (12)	0.0457 (11)	0.0477 (11)	−0.0043 (9)	0.0069 (9)	0.0008 (9)
C10	0.0518 (12)	0.0497 (11)	0.0525 (12)	−0.0099 (9)	0.0122 (9)	−0.0013 (9)
C11	0.0491 (12)	0.0511 (12)	0.0527 (11)	−0.0076 (9)	0.0057 (9)	0.0029 (9)
C12	0.0474 (12)	0.0519 (12)	0.0561 (12)	−0.0085 (9)	0.0078 (9)	−0.0001 (9)
C13	0.0482 (12)	0.0515 (12)	0.0538 (11)	−0.0069 (9)	0.0053 (9)	0.0040 (9)

S1—C2	1.744 (2)	C6—C7	1.382 (3)
S1—C1	1.753 (2)	C6—H6A	0.9300
O1—C9	1.313 (2)	C8—H8A	0.9600
O1—H1	0.8200	C8—H8B	0.9600
O2—C9	1.209 (2)	C8—H8C	0.9600
N1—C1	1.308 (2)	C9—C10	1.499 (3)
N1—C7	1.397 (2)	C10—C11	1.508 (3)
N2—C1	1.329 (2)	C10—H10A	0.9700
N2—H2A	0.8600	C10—H10B	0.9700
N2—H2B	0.8600	C11—C12	1.514 (3)
C2—C3	1.385 (3)	C11—H11A	0.9700
C2—C7	1.395 (3)	C11—H11B	0.9700
C3—C4	1.385 (3)	C12—C13	1.510 (3)
C3—H3A	0.9300	C12—H12A	0.9700
C4—C5	1.388 (3)	C12—H12B	0.9700
C4—C8	1.516 (3)	C13—C13i	1.513 (4)
C5—C6	1.375 (3)	C13—H13A	0.9700
C5—H5A	0.9300	C13—H13B	0.9700
C2—S1—C1	89.34 (9)	C4—C8—H8C	109.5
C9—O1—H1	109.5	H8A—C8—H8C	109.5
C1—N1—C7	111.53 (16)	H8B—C8—H8C	109.5
C1—N2—H2A	120.0	O2—C9—O1	123.13 (17)
C1—N2—H2B	120.0	O2—C9—C10	123.42 (18)
H2A—N2—H2B	120.0	O1—C9—C10	113.44 (16)
N1—C1—N2	123.95 (18)	C9—C10—C11	114.71 (16)
N1—C1—S1	114.85 (15)	C9—C10—H10A	108.6
N2—C1—S1	121.18 (15)	C11—C10—H10A	108.6
C3—C2—C7	121.1 (2)	C9—C10—H10B	108.6
C3—C2—S1	129.25 (16)	C11—C10—H10B	108.6
C7—C2—S1	109.65 (15)	H10A—C10—H10B	107.6
C4—C3—C2	119.7 (2)	C10—C11—C12	112.90 (16)
C4—C3—H3A	120.2	C10—C11—H11A	109.0
C2—C3—H3A	120.2	C12—C11—H11A	109.0
C3—C4—C5	118.4 (2)	C10—C11—H11B	109.0
C3—C4—C8	120.8 (2)	C12—C11—H11B	109.0
C5—C4—C8	120.8 (2)	H11A—C11—H11B	107.8
C6—C5—C4	122.6 (2)	C13—C12—C11	113.84 (16)
C6—C5—H5A	118.7	C13—C12—H12A	108.8
C4—C5—H5A	118.7	C11—C12—H12A	108.8
C5—C6—C7	118.9 (2)	C13—C12—H12B	108.8
C5—C6—H6A	120.6	C11—C12—H12B	108.8
C7—C6—H6A	120.6	H12A—C12—H12B	107.7
C6—C7—C2	119.34 (19)	C12—C13—C13i	114.4 (2)
C6—C7—N1	126.03 (18)	C12—C13—H13A	108.7
C2—C7—N1	114.63 (17)	C13i—C13—H13A	108.7
C4—C8—H8A	109.5	C12—C13—H13B	108.7
C4—C8—H8B	109.5	C13i—C13—H13B	108.7
H8A—C8—H8B	109.5	H13A—C13—H13B	107.6
C7—N1—C1—N2	−179.62 (19)	C5—C6—C7—C2	−0.2 (3)
C7—N1—C1—S1	−0.5 (2)	C5—C6—C7—N1	−179.8 (2)
C2—S1—C1—N1	0.29 (17)	C3—C2—C7—C6	0.0 (3)
C2—S1—C1—N2	179.42 (18)	S1—C2—C7—C6	−179.96 (17)
C1—S1—C2—C3	−180.0 (2)	C3—C2—C7—N1	179.69 (19)
C1—S1—C2—C7	0.02 (16)	S1—C2—C7—N1	−0.3 (2)
C7—C2—C3—C4	0.5 (3)	C1—N1—C7—C6	−179.8 (2)
S1—C2—C3—C4	−179.45 (19)	C1—N1—C7—C2	0.5 (3)
C2—C3—C4—C5	−0.9 (4)	O2—C9—C10—C11	4.3 (3)
C2—C3—C4—C8	179.8 (2)	O1—C9—C10—C11	−176.76 (17)
C3—C4—C5—C6	0.8 (4)	C9—C10—C11—C12	−173.70 (17)
C8—C4—C5—C6	−179.9 (2)	C10—C11—C12—C13	−179.12 (17)
C4—C5—C6—C7	−0.2 (4)	C11—C12—C13—C13i	−178.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.597 (2)	171
N2—H2A···O2	0.86	2.09	2.914 (2)	161
N2—H2B···O1ii	0.86	2.14	2.954 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.78	2.597 (2)	171
N2—H2A⋯O2	0.86	2.09	2.914 (2)	161
N2—H2B⋯O1i	0.86	2.14	2.954 (2)	157

Symmetry code: (i) .