2-[(1,3-Benzo­thia­zol-2-yl)imino­meth­yl]-6-meth­oxy­phenol: a new monoclinic polymorph

Affan, M.A.; Jessop, P.G.; Salam, M.A.; Halim, S.N.B.A.; Tiekink, E.R.T.

doi:10.1107/S1600536813019387

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1273

doi:10.1107/S1600536813019387

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2-[(1,3-Benzothiazol-2-yl)iminomethyl]-6-methoxyphenol: a new monoclinic polymorph

Md. Abu Affan,^a ‡ Philip G. Jessop,^a Md. Abdus Salam,^b Siti Nadiah Binti Abdul Halim ^c and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada, ^bFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samaharan, Sawarak, Malaysia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 13 July 2013; accepted 13 July 2013; online 20 July 2013)

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 benzothiazole (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 methoxy 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 intramolecular O—H⋯N hydrogen bond and the hydroxy O and thioether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C—H⋯O interactions and linked by π–π interactions between the thiazole 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_r = 284.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.095
S = 1.05
2983 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x+1, -y, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019387/su2623sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813019387/su2623Isup3.cml

checkCIF report

Comment top

The title compound, (I), was prepared in connection with on-going studies of organotin compounds with N, O and S donors for evaluation for biological activity (Affan et al., 2009).

In (I), Fig. 1, the dihedral angle between the benzothiazole (r.m.s. deviation = 0.010 Å) and the benzene ring is 7.86 (6)°. This, coupled with the observation that the methoxy substituent is coplanar with the benzene ring to which it is attached, the C15—O2—C11—C10 torsion angle is 178.31 (14)°, indicates that the molecule is approximately planar. Indeed, the r.m.s. deviation for all 20 non-hydrogen atoms is 0.083 Å, with maximum deviations of 0.123 (1) Å for the S1 atom and -0.148 (2) Å for C3. As seen from the overlay diagram in Fig. 2, this conformation is similar to that found in the P2₁/n polymorph, for which the dihedral angle between the benzothiazole and benzene ring is 10.76 (10)° (Büyükgüngör et al., 2004). The coplanarity about the imine C8═N2 bond [1.287 (2) Å], with an E conformation, enables the formation of an intramolecular O—H···N hydrogen bond, Table 1. The hydroxyl-O and thioether-S atoms are syn.

In the crystal packing, centrosymmetrically related molecules associate into dimers via C—H···O interactions and stack in columns along the b axis via π–π interactions between the thiazole and benzene rings [inter-centroid distance = 3.8256 (10) Å, angle of inclination = 7.47 (8)° for symmetry operation x, -1 + y, z], Fig. 3 and Table 1.

Related literature top

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 top

2-Aminobenzothiazole (0.765 g, 5 mmol) in ethanol (10 ml) was added to an ethanolic solution of 4-(aminomethyl)-2-methoxyphenol (0.751 g, 5 mmol) and the reaction mixture was refluxed for 2 h. After cooling, a yellow solid was filtered off and washed with cold ethanol. The title compound (I) was obtained after recrystallization from its methanol solution [m.p. 466–468 K, yield 1.18 g (78%)].

Computing details top

Data collection: SMART (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. Superimposition of the molecule in (I) (red image) on that found in the polymorph (blue image). The five-membered rings have been superimposed.
	Fig. 3. A view in projection down the b axis of the unit-cell contents for (I). The C—H···O and π—π interactions are shown as orange and purple dashed lines, respectively.

2-[(1,3-Benzothiazol-2-yl)iminomethyl]-6-methoxyphenol top

Crystal data top

C₁₅H₁₂N₂O₂S	F(000) = 592
M_r = 284.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0424P)² + 0.3573P] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O₂S	V = 1307.1 (2) Å³
M_r = 284.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6697 (11) Å	µ = 0.25 mm⁻¹
b = 6.0250 (6) Å	T = 100 K
c = 18.6441 (18) Å	0.20 × 0.16 × 0.15 mm
β = 94.346 (1)°

Data collection top

Bruker SMART APEX diffractometer	2983 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2404 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.746	R_int = 0.046
15750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
2983 reflections	Δρ_min = −0.26 e Å⁻³
183 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Footnotes

‡Additional correspondence author, e-mail: maaffan@gmail.com.

Acknowledgements

The authors thank the Natural Sciences and Engineering Council of Canada for support. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR-MOHE/SC/03).

References

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Volume 69| Part 8| August 2013| Page o1273

doi:10.1107/S1600536813019387

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[(1,3-Benzo­thia­zol-2-yl)imino­meth­yl]-6-meth­­oxy­phenol: a new monoclinic polymorph

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-[(1,3-Benzothiazol-2-yl)iminomethyl]-6-methoxyphenol: a new monoclinic polymorph