2-[(1,3-Benzo-thia-zol-2-yl)imino-meth-yl]-6-meth-oxy-phenol: a new monoclinic polymorph.

The title compound, C15H12N2O2S, is a P21/c polymorph of a previously reported P21/n polymorph [Büyükgüngör et al. (2004 ▶). Acta Cryst. E60, o1414-o1416]. The dihedral angle between the benzo-thia-zole (r.m.s. deviation = 0.010 Å) and the benzene ring of 7.86 (6)° compares with 10.76 (10)° in the literature structure. The meth-oxy substituent is almost coplanar with the benzene ring to which it is attached [C-O-C-C torsion angle = 178.31 (14)°] and the conformation about the imine bond [1.287 (2) Å] is E. There is an intra-molecular O-H⋯N hydrogen bond and the hy-droxy O and thio-ether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C-H⋯O inter-actions and linked by π-π inter-actions between the thia-zole and benzene rings [centroid-to-centroid distance = 3.8256 (10) Å].

Related literature

For background to the biological activity of organotin compounds with N-, O- and S-atom donors, see: Affan et al. (2009 ▶). For the structure of the P21/n polymorph, see: Büyükgüngör et al. (2004 ▶).

Experimental

Crystal data

C15H12N2O2S

M = 284.33

Monoclinic,

a = 11.6697 (11) Å

b = 6.0250 (6) Å

c = 18.6441 (18) Å

β = 94.346 (1)°

V = 1307.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.669, T max = 0.746

15750 measured reflections

2983 independent reflections

2404 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.05

2983 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019387/su2623sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019387/su2623Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019387/su2623Isup3.cml

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

C15H12N2O2S	F(000) = 592
Mr = 284.33	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2808 reflections
a = 11.6697 (11) Å	θ = 2.7–26.6°
b = 6.0250 (6) Å	µ = 0.25 mm−1
c = 18.6441 (18) Å	T = 100 K
β = 94.346 (1)°	Block, yellow
V = 1307.1 (2) Å3	0.20 × 0.16 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2404 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.669, Tmax = 0.746	k = −7→7
15750 measured reflections	l = −23→24

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.3573P] where P = (Fo2 + 2Fc2)/3
2983 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.40036 (3)	−0.28845 (7)	0.51769 (2)	0.02579 (13)
O1	0.38182 (9)	0.30422 (19)	0.37054 (6)	0.0291 (3)
H1O	0.3754	0.1918	0.3966	0.044*
O2	0.37477 (10)	0.6591 (2)	0.29096 (6)	0.0319 (3)
N1	0.17783 (11)	−0.3057 (2)	0.49353 (7)	0.0242 (3)
N2	0.27272 (11)	−0.0044 (2)	0.43688 (7)	0.0233 (3)
C1	0.32893 (13)	−0.5026 (3)	0.55699 (8)	0.0231 (3)
C2	0.21017 (13)	−0.4851 (3)	0.53783 (8)	0.0232 (3)
C3	0.13496 (15)	−0.6425 (3)	0.56295 (9)	0.0301 (4)
H3	0.0549	−0.6355	0.5495	0.036*
C4	0.17954 (16)	−0.8081 (3)	0.60766 (10)	0.0335 (4)
H4	0.1292	−0.9150	0.6257	0.040*
C5	0.29730 (16)	−0.8223 (3)	0.62712 (9)	0.0318 (4)
H5	0.3253	−0.9383	0.6582	0.038*
C6	0.37344 (15)	−0.6718 (3)	0.60217 (9)	0.0278 (4)
H6	0.4535	−0.6826	0.6152	0.033*
C7	0.26852 (13)	−0.1942 (3)	0.47956 (8)	0.0228 (3)
C8	0.17759 (14)	0.0866 (3)	0.41305 (8)	0.0241 (3)
H8	0.1071	0.0233	0.4253	0.029*
C9	0.17491 (13)	0.2822 (3)	0.36818 (8)	0.0225 (3)
C10	0.27665 (13)	0.3830 (3)	0.34943 (8)	0.0221 (3)
C11	0.27064 (14)	0.5760 (3)	0.30645 (8)	0.0235 (3)
C12	0.16509 (14)	0.6647 (3)	0.28398 (8)	0.0265 (4)
H12	0.1612	0.7948	0.2551	0.032*
C13	0.06360 (15)	0.5648 (3)	0.30329 (9)	0.0298 (4)
H13	−0.0088	0.6272	0.2876	0.036*
C14	0.06870 (14)	0.3774 (3)	0.34480 (9)	0.0274 (4)
H14	−0.0004	0.3108	0.3580	0.033*
C15	0.37379 (17)	0.8514 (3)	0.24585 (10)	0.0353 (4)
H15A	0.3302	0.8193	0.2000	0.053*
H15B	0.4529	0.8914	0.2369	0.053*
H15C	0.3377	0.9751	0.2697	0.053*

	U11	U22	U33	U12	U13	U23
S1	0.0245 (2)	0.0231 (2)	0.0297 (2)	0.00138 (16)	0.00111 (16)	0.00382 (17)
O1	0.0241 (6)	0.0283 (7)	0.0344 (7)	0.0017 (5)	−0.0005 (5)	0.0084 (5)
O2	0.0308 (6)	0.0303 (7)	0.0348 (7)	−0.0024 (5)	0.0041 (5)	0.0105 (5)
N1	0.0272 (7)	0.0211 (7)	0.0243 (7)	0.0006 (5)	0.0013 (5)	0.0008 (5)
N2	0.0280 (7)	0.0181 (7)	0.0234 (7)	0.0004 (5)	0.0006 (5)	0.0010 (5)
C1	0.0289 (8)	0.0202 (8)	0.0208 (7)	0.0005 (6)	0.0047 (6)	−0.0015 (6)
C2	0.0293 (8)	0.0198 (8)	0.0206 (7)	0.0020 (6)	0.0036 (6)	−0.0013 (6)
C3	0.0318 (9)	0.0286 (9)	0.0307 (9)	−0.0012 (7)	0.0065 (7)	0.0018 (7)
C4	0.0412 (10)	0.0267 (9)	0.0342 (9)	−0.0031 (8)	0.0122 (8)	0.0049 (7)
C5	0.0466 (11)	0.0239 (9)	0.0257 (9)	0.0065 (8)	0.0075 (8)	0.0051 (7)
C6	0.0327 (9)	0.0264 (9)	0.0244 (8)	0.0060 (7)	0.0027 (7)	0.0016 (7)
C7	0.0263 (8)	0.0210 (8)	0.0209 (8)	0.0015 (6)	0.0008 (6)	−0.0021 (6)
C8	0.0259 (8)	0.0223 (8)	0.0242 (8)	−0.0028 (6)	0.0018 (6)	−0.0014 (6)
C9	0.0272 (8)	0.0201 (8)	0.0199 (7)	0.0001 (6)	0.0000 (6)	−0.0018 (6)
C10	0.0251 (8)	0.0212 (8)	0.0197 (7)	0.0016 (6)	−0.0006 (6)	−0.0028 (6)
C11	0.0293 (8)	0.0209 (8)	0.0203 (7)	−0.0023 (6)	0.0019 (6)	−0.0015 (6)
C12	0.0345 (9)	0.0226 (8)	0.0218 (8)	0.0028 (7)	−0.0014 (7)	0.0024 (6)
C13	0.0288 (9)	0.0290 (9)	0.0310 (9)	0.0046 (7)	−0.0028 (7)	0.0028 (7)
C14	0.0254 (8)	0.0260 (9)	0.0305 (9)	−0.0013 (7)	0.0003 (7)	0.0009 (7)
C15	0.0453 (11)	0.0259 (9)	0.0356 (10)	−0.0051 (8)	0.0092 (8)	0.0063 (8)

S1—C1	1.7289 (16)	C5—C6	1.375 (2)
S1—C7	1.7404 (16)	C5—H5	0.9500
O1—C10	1.3466 (18)	C6—H6	0.9500
O1—H1O	0.8400	C8—C9	1.444 (2)
O2—C11	1.3653 (19)	C8—H8	0.9500
O2—C15	1.431 (2)	C9—C10	1.401 (2)
N1—C7	1.296 (2)	C9—C14	1.405 (2)
N1—C2	1.395 (2)	C10—C11	1.411 (2)
N2—C8	1.287 (2)	C11—C12	1.378 (2)
N2—C7	1.396 (2)	C12—C13	1.400 (2)
C1—C6	1.397 (2)	C12—H12	0.9500
C1—C2	1.409 (2)	C13—C14	1.368 (2)
C2—C3	1.397 (2)	C13—H13	0.9500
C3—C4	1.377 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.397 (3)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C1—S1—C7	88.67 (8)	N2—C8—H8	119.1
C10—O1—H1O	109.5	C9—C8—H8	119.1
C11—O2—C15	116.98 (13)	C10—C9—C14	119.33 (14)
C7—N1—C2	109.40 (13)	C10—C9—C8	121.11 (14)
C8—N2—C7	118.64 (14)	C14—C9—C8	119.53 (15)
C6—C1—C2	121.41 (15)	O1—C10—C9	123.02 (14)
C6—C1—S1	129.12 (13)	O1—C10—C11	117.49 (14)
C2—C1—S1	109.47 (12)	C9—C10—C11	119.50 (14)
C3—C2—N1	125.17 (15)	O2—C11—C12	125.64 (15)
C3—C2—C1	119.68 (15)	O2—C11—C10	114.56 (14)
N1—C2—C1	115.15 (14)	C12—C11—C10	119.80 (15)
C4—C3—C2	118.49 (16)	C11—C12—C13	120.61 (15)
C4—C3—H3	120.8	C11—C12—H12	119.7
C2—C3—H3	120.8	C13—C12—H12	119.7
C3—C4—C5	121.37 (16)	C14—C13—C12	119.95 (15)
C3—C4—H4	119.3	C14—C13—H13	120.0
C5—C4—H4	119.3	C12—C13—H13	120.0
C6—C5—C4	121.34 (16)	C13—C14—C9	120.81 (16)
C6—C5—H5	119.3	C13—C14—H14	119.6
C4—C5—H5	119.3	C9—C14—H14	119.6
C5—C6—C1	117.70 (16)	O2—C15—H15A	109.5
C5—C6—H6	121.1	O2—C15—H15B	109.5
C1—C6—H6	121.1	H15A—C15—H15B	109.5
N1—C7—N2	127.11 (14)	O2—C15—H15C	109.5
N1—C7—S1	117.30 (12)	H15A—C15—H15C	109.5
N2—C7—S1	115.58 (11)	H15B—C15—H15C	109.5
N2—C8—C9	121.88 (15)
C7—S1—C1—C6	−179.01 (16)	C1—S1—C7—N2	−179.79 (12)
C7—S1—C1—C2	0.03 (12)	C7—N2—C8—C9	−179.54 (13)
C7—N1—C2—C3	−179.18 (15)	N2—C8—C9—C10	−0.8 (2)
C7—N1—C2—C1	0.46 (19)	N2—C8—C9—C14	−178.75 (15)
C6—C1—C2—C3	−1.5 (2)	C14—C9—C10—O1	179.00 (14)
S1—C1—C2—C3	179.37 (12)	C8—C9—C10—O1	1.1 (2)
C6—C1—C2—N1	178.85 (14)	C14—C9—C10—C11	−1.1 (2)
S1—C1—C2—N1	−0.28 (17)	C8—C9—C10—C11	−178.97 (14)
N1—C2—C3—C4	−178.67 (15)	C15—O2—C11—C12	−1.8 (2)
C1—C2—C3—C4	1.7 (2)	C15—O2—C11—C10	178.31 (14)
C2—C3—C4—C5	−0.9 (3)	O1—C10—C11—O2	0.5 (2)
C3—C4—C5—C6	−0.2 (3)	C9—C10—C11—O2	−179.46 (13)
C4—C5—C6—C1	0.5 (2)	O1—C10—C11—C12	−179.39 (14)
C2—C1—C6—C5	0.4 (2)	C9—C10—C11—C12	0.7 (2)
S1—C1—C6—C5	179.32 (13)	O2—C11—C12—C13	−179.97 (15)
C2—N1—C7—N2	179.60 (14)	C10—C11—C12—C13	−0.1 (2)
C2—N1—C7—S1	−0.44 (17)	C11—C12—C13—C14	0.0 (3)
C8—N2—C7—N1	6.8 (2)	C12—C13—C14—C9	−0.4 (3)
C8—N2—C7—S1	−173.12 (12)	C10—C9—C14—C13	0.9 (2)
C1—S1—C7—N1	0.25 (13)	C8—C9—C14—C13	178.87 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.84	1.88	2.6167 (17)	146
C6—H6···O2i	0.95	2.56	3.424 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.84	1.88	2.6167 (17)	146
C6—H6⋯O2i	0.95	2.56	3.424 (2)	151

Symmetry code: (i) .