2-({[4-(1,3-Benzothia­zol-2-yl)phen­yl]amino}methyl)­phenol

Potgieter, K.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536811051580

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o27

doi:10.1107/S1600536811051580

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2-({[4-(1,3-Benzothiazol-2-yl)phenyl]amino}methyl)phenol

Kim Potgieter,^a Thomas Gerber,^a Eric Hosten ^a and Richard Betz ^a ^*

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 3 November 2011; accepted 30 November 2011; online 3 December 2011)

In the title compound, C₂₀H₁₆N₂OS, the aniline substituent essentially coplanar with the benzothiazole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å). The phenol group is almost perpendicular to the benzothiazolylaniline group, with an interplanar angle of 88.36 (2)°. In the crystal, molecules aggregate as centrosymmetric dimers by pairs of O—H⋯N hydrogen bonds. C—H⋯O contacts and N—H⋯π(arene) interactions also occur.

Related literature

For general information about rhenium-supported radio-pharmaceuticals, see: Gerber et al. (2011 ). For the crystal structure of 4-(1,3-benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate, see: Su et al. (2009 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₆N₂OS
M_r = 332.41
Monoclinic, P 2₁ /c
a = 13.3260 (4) Å
b = 5.7940 (1) Å
c = 24.2246 (6) Å
β = 121.546 (1)°
V = 1593.99 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 200 K
0.44 × 0.17 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.929, T_max = 1.000
15126 measured reflections
3953 independent reflections
3272 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.03
3953 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	1.95	2.7459 (14)	164
C26—H26⋯O1ⁱ	0.95	2.48	3.3645 (16)	156
N2—H72⋯Cgⁱⁱ	0.82 (2)	2.61 (2)	3.4024 (14)	163.0 (19)
Symmetry codes: (i) -x, -y, -z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811051580/gg2063sup1.cif

Supporting information file. DOI: 10.1107/S1600536811051580/gg2063Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051580/gg2063Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536811051580/gg2063Isup4.cml

checkCIF report

Comment top

In our continuous efforts to create new radio-pharmaceuticals (Gerber et al., 2011), we attempted the coordination reaction of a potentially multidentate ligand towards a rhenium precursor upon which a crystalline reaction product was obtained. The crystal structure analysis showed the presence of the free ligand only whose molecular and crystal structure has not been reported to date. The structure of 4-(1,3-benzothiazol-2-yl)-N-(2-pyridylmethyl) aniline monohydrate is noted in the literature (Su et al., 2009).

The benzothiazolyl system and the attached aniline system are nearly co-planar (r.m.s. of all fitted non-hydrogen atoms including the nitrogen bound methylene group = 0.0612 Å). The phenolic substituent, however, adopts a nearly perpendicular orientation with respect to the rest of the molecule, with an interplanar angle of 88.36 (2)° between the two least-squares planes defined by both moieties (Fig. 1).

In the crystal, classical hydrogen bonds of the O–H···N type as well as C–H···O contacts (whose range lies by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating) are observed. The latter are supported by one of the hydrogen atoms of the central phenyl ring. In total, the molecules are connected to centrosymmetric dimers by these two interactions. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is R²₂(18)R²₂(24) on the unitary level. The nitrogen-bonded hydrogen atom forms a hydrogen bond to the aromatic system of the phenolic moiety, connecting the molecules to chains along the crystallographic b axis. Metrical parameters about these contacts as well as information about their symmetry is listed in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 4.6019 (10) Å and is apparent between the phenyl unit of the benzothiazole moiety and the central C₆ aromatic ring (Fig 2.)

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For general information about rhenium-supported radio-pharmaceuticals, see: Gerber et al. (2011). For the crystal structure of 4-(1,3-benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate, see: Su et al. (2009). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

A mixture of 2.00 g of 4-aminobenzoic acid and 1.33 g of 2-aminothiophenol was added to hot polyphosphoric acid. The stirring solution was heated to 220 °C for four hours. The reaction solution was cooled to room temperature and poured into a 10% K₂CO₃ solution. The yellow precipitate which formed was filtered and dried under vacuum, yielding 4-(benzo[d]thiazol-2-yl)benzenamine. A solution of 1.0 g of this product dissolved in 25 cm³ of methanol was added to a 25 cm³ methanol solution of 2-hydroxybenzaldehyde (0.4 g). The solution was refluxed for three hours after which it was cooled to room temperature and stirred overnight. An excess of NaBH₄ (2.0 g) was added in portions with stirring and the mixture was left to stir at room temperature overnight. The solvent was removed by evaporation and 50 cm³ of water was added. HCl was added to adjust the pH to 6, resulting in the formation of a light yellow precipitate which was filtered and dried under vacuum. Crystals suitable for the X-ray diffraction study were obtained upon the attempted synthesis of a rhenium coordination compound in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 1 0]. Blue dashed lines indicate classical hydrogen bonds of the O–H···N type, green dashed lines indicate C–H···O contacts. Symmetry operator: ⁱ -x, -y, -z.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

2-({[4-(1,3-Benzothiazol-2-yl)phenyl]amino}methyl)phenol top

Crystal data top

C₂₀H₁₆N₂OS	F(000) = 696
M_r = 332.41	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 7469 reflections
a = 13.3260 (4) Å	θ = 3.1–28.3°
b = 5.7940 (1) Å	µ = 0.21 mm⁻¹
c = 24.2246 (6) Å	T = 200 K
β = 121.546 (1)°	Platelet, brown
V = 1593.99 (7) Å³	0.44 × 0.17 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3953 independent reflections
Radiation source: fine-focus sealed tube	3272 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
T_min = 0.929, T_max = 1.000	k = −4→7
15126 measured reflections	l = −31→32

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0417P)² + 0.6757P] where P = (F_o² + 2F_c²)/3
3953 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₆N₂OS	V = 1593.99 (7) Å³
M_r = 332.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3260 (4) Å	µ = 0.21 mm⁻¹
b = 5.7940 (1) Å	T = 200 K
c = 24.2246 (6) Å	0.44 × 0.17 × 0.11 mm
β = 121.546 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3953 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3272 reflections with I > 2σ(I)
T_min = 0.929, T_max = 1.000	R_int = 0.018
15126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
3953 reflections	Δρ_min = −0.23 e Å⁻³
221 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.42147 (3)	0.68632 (6)	0.257240 (17)	0.03011 (10)
O1	−0.15303 (8)	0.05617 (17)	−0.19880 (5)	0.0317 (2)
H1	−0.1951	−0.0563	−0.2167	0.048*
N1	0.31149 (9)	0.30173 (19)	0.24291 (5)	0.0264 (2)
N2	0.09494 (11)	0.5026 (2)	−0.06249 (6)	0.0317 (3)
H72	0.1055 (16)	0.621 (4)	−0.0774 (9)	0.049 (5)*
C1	0.32433 (11)	0.4656 (2)	0.20995 (6)	0.0246 (3)
C2	0.00373 (12)	0.3473 (2)	−0.10753 (6)	0.0291 (3)
H2A	−0.0541	0.4367	−0.1460	0.035*
H2B	−0.0380	0.2851	−0.0869	0.035*
C11	0.44852 (11)	0.5440 (2)	0.32639 (7)	0.0284 (3)
C12	0.38217 (11)	0.3396 (2)	0.30904 (6)	0.0273 (3)
C13	0.39226 (13)	0.1916 (3)	0.35715 (7)	0.0343 (3)
H13	0.3484	0.0521	0.3461	0.041*
C14	0.46741 (14)	0.2528 (3)	0.42110 (7)	0.0398 (3)
H14	0.4755	0.1534	0.4544	0.048*
C15	0.53187 (13)	0.4580 (3)	0.43785 (7)	0.0390 (3)
H15	0.5821	0.4962	0.4823	0.047*
C16	0.52407 (12)	0.6063 (3)	0.39127 (7)	0.0344 (3)
H16	0.5683	0.7454	0.4028	0.041*
C21	0.26744 (11)	0.4708 (2)	0.13979 (6)	0.0254 (3)
C22	0.27965 (12)	0.6609 (2)	0.10797 (7)	0.0295 (3)
H22	0.3280	0.7866	0.1328	0.035*
C23	0.22327 (12)	0.6691 (2)	0.04174 (7)	0.0305 (3)
H23	0.2331	0.8004	0.0215	0.037*
C24	0.15098 (11)	0.4861 (2)	0.00317 (6)	0.0266 (3)
C25	0.14071 (12)	0.2928 (2)	0.03483 (7)	0.0296 (3)
H25	0.0941	0.1652	0.0101	0.035*
C26	0.19777 (12)	0.2865 (2)	0.10154 (6)	0.0286 (3)
H26	0.1896	0.1541	0.1220	0.034*
C31	0.04626 (11)	0.1472 (2)	−0.12987 (6)	0.0250 (3)
C32	−0.03897 (11)	0.0004 (2)	−0.17724 (6)	0.0258 (3)
C33	−0.00650 (12)	−0.1827 (2)	−0.20165 (6)	0.0306 (3)
H33	−0.0649	−0.2806	−0.2340	0.037*
C34	0.11211 (13)	−0.2216 (3)	−0.17839 (7)	0.0351 (3)
H34	0.1348	−0.3467	−0.1949	0.042*
C35	0.19715 (12)	−0.0793 (3)	−0.13149 (7)	0.0343 (3)
H35	0.2781	−0.1073	−0.1155	0.041*
C36	0.16400 (11)	0.1046 (3)	−0.10779 (6)	0.0302 (3)
H36	0.2228	0.2031	−0.0759	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02935 (17)	0.02586 (17)	0.03296 (18)	−0.00579 (12)	0.01480 (14)	−0.00429 (13)
O1	0.0241 (5)	0.0321 (5)	0.0340 (5)	−0.0054 (4)	0.0118 (4)	−0.0005 (4)
N1	0.0234 (5)	0.0264 (5)	0.0283 (5)	−0.0015 (4)	0.0129 (4)	−0.0011 (4)
N2	0.0387 (7)	0.0273 (6)	0.0282 (6)	−0.0073 (5)	0.0170 (5)	−0.0016 (5)
C1	0.0209 (6)	0.0219 (6)	0.0310 (6)	−0.0003 (4)	0.0137 (5)	−0.0028 (5)
C2	0.0284 (6)	0.0303 (7)	0.0277 (6)	−0.0025 (5)	0.0139 (5)	−0.0015 (5)
C11	0.0235 (6)	0.0298 (7)	0.0322 (7)	0.0015 (5)	0.0147 (5)	−0.0033 (5)
C12	0.0227 (6)	0.0293 (6)	0.0297 (6)	0.0017 (5)	0.0137 (5)	−0.0015 (5)
C13	0.0342 (7)	0.0341 (7)	0.0349 (7)	0.0010 (6)	0.0182 (6)	0.0023 (6)
C14	0.0390 (8)	0.0489 (9)	0.0314 (7)	0.0077 (7)	0.0184 (6)	0.0055 (7)
C15	0.0305 (7)	0.0531 (9)	0.0281 (7)	0.0051 (6)	0.0117 (6)	−0.0059 (6)
C16	0.0264 (6)	0.0396 (8)	0.0342 (7)	0.0003 (6)	0.0138 (6)	−0.0093 (6)
C21	0.0231 (6)	0.0245 (6)	0.0300 (6)	0.0003 (5)	0.0149 (5)	−0.0010 (5)
C22	0.0281 (6)	0.0244 (6)	0.0332 (7)	−0.0057 (5)	0.0142 (6)	−0.0027 (5)
C23	0.0328 (7)	0.0252 (6)	0.0339 (7)	−0.0044 (5)	0.0177 (6)	0.0018 (5)
C24	0.0275 (6)	0.0246 (6)	0.0299 (6)	0.0004 (5)	0.0166 (5)	−0.0007 (5)
C25	0.0352 (7)	0.0237 (6)	0.0314 (7)	−0.0058 (5)	0.0186 (6)	−0.0043 (5)
C26	0.0346 (7)	0.0228 (6)	0.0321 (7)	−0.0030 (5)	0.0201 (6)	−0.0009 (5)
C31	0.0266 (6)	0.0275 (6)	0.0216 (6)	−0.0027 (5)	0.0131 (5)	0.0017 (5)
C32	0.0253 (6)	0.0294 (6)	0.0211 (6)	−0.0027 (5)	0.0111 (5)	0.0038 (5)
C33	0.0344 (7)	0.0301 (7)	0.0236 (6)	−0.0045 (5)	0.0128 (5)	−0.0019 (5)
C34	0.0400 (8)	0.0370 (8)	0.0309 (7)	0.0022 (6)	0.0204 (6)	−0.0031 (6)
C35	0.0279 (7)	0.0420 (8)	0.0337 (7)	0.0009 (6)	0.0165 (6)	−0.0007 (6)
C36	0.0260 (6)	0.0350 (7)	0.0274 (6)	−0.0046 (5)	0.0124 (5)	−0.0023 (5)

Geometric parameters (Å, º) top

S1—C11	1.7275 (14)	C16—H16	0.9500
S1—C1	1.7526 (13)	C21—C26	1.3999 (18)
O1—C32	1.3627 (15)	C21—C22	1.4018 (18)
O1—H1	0.8200	C22—C23	1.3709 (19)
N1—C1	1.3082 (17)	C22—H22	0.9500
N1—C12	1.3866 (16)	C23—C24	1.4083 (18)
N2—C24	1.3616 (17)	C23—H23	0.9500
N2—C2	1.4459 (17)	C24—C25	1.4038 (18)
N2—H72	0.82 (2)	C25—C26	1.3804 (19)
C1—C21	1.4547 (18)	C25—H25	0.9500
C2—C31	1.5098 (19)	C26—H26	0.9500
C2—H2A	0.9900	C31—C36	1.3893 (18)
C2—H2B	0.9900	C31—C32	1.4022 (17)
C11—C16	1.3995 (19)	C32—C33	1.3890 (19)
C11—C12	1.4042 (19)	C33—C34	1.391 (2)
C12—C13	1.3954 (19)	C33—H33	0.9500
C13—C14	1.380 (2)	C34—C35	1.381 (2)
C13—H13	0.9500	C34—H34	0.9500
C14—C15	1.397 (2)	C35—C36	1.388 (2)
C14—H14	0.9500	C35—H35	0.9500
C15—C16	1.378 (2)	C36—H36	0.9500
C15—H15	0.9500

C11—S1—C1	89.62 (6)	C22—C21—C1	121.28 (11)
C32—O1—H1	109.4	C23—C22—C21	121.38 (12)
C1—N1—C12	111.32 (11)	C23—C22—H22	119.3
C24—N2—C2	124.65 (12)	C21—C22—H22	119.3
C24—N2—H72	117.2 (13)	C22—C23—C24	121.07 (12)
C2—N2—H72	117.3 (13)	C22—C23—H23	119.5
N1—C1—C21	124.99 (11)	C24—C23—H23	119.5
N1—C1—S1	114.74 (10)	N2—C24—C25	122.93 (12)
C21—C1—S1	120.26 (9)	N2—C24—C23	119.26 (12)
N2—C2—C31	115.06 (11)	C25—C24—C23	117.81 (12)
N2—C2—H2A	108.5	C26—C25—C24	120.60 (12)
C31—C2—H2A	108.5	C26—C25—H25	119.7
N2—C2—H2B	108.5	C24—C25—H25	119.7
C31—C2—H2B	108.5	C25—C26—C21	121.54 (12)
H2A—C2—H2B	107.5	C25—C26—H26	119.2
C16—C11—C12	121.61 (13)	C21—C26—H26	119.2
C16—C11—S1	128.92 (11)	C36—C31—C32	118.40 (12)
C12—C11—S1	109.46 (10)	C36—C31—C2	123.94 (12)
N1—C12—C13	125.32 (12)	C32—C31—C2	117.63 (11)
N1—C12—C11	114.83 (12)	O1—C32—C33	123.46 (12)
C13—C12—C11	119.84 (13)	O1—C32—C31	115.67 (12)
C14—C13—C12	118.43 (14)	C33—C32—C31	120.80 (12)
C14—C13—H13	120.8	C32—C33—C34	119.49 (12)
C12—C13—H13	120.8	C32—C33—H33	120.3
C13—C14—C15	121.28 (15)	C34—C33—H33	120.3
C13—C14—H14	119.4	C35—C34—C33	120.40 (13)
C15—C14—H14	119.4	C35—C34—H34	119.8
C16—C15—C14	121.42 (14)	C33—C34—H34	119.8
C16—C15—H15	119.3	C34—C35—C36	119.79 (13)
C14—C15—H15	119.3	C34—C35—H35	120.1
C15—C16—C11	117.41 (14)	C36—C35—H35	120.1
C15—C16—H16	121.3	C35—C36—C31	121.11 (12)
C11—C16—H16	121.3	C35—C36—H36	119.4
C26—C21—C22	117.56 (12)	C31—C36—H36	119.4
C26—C21—C1	121.16 (11)

C12—N1—C1—C21	176.61 (11)	C1—C21—C22—C23	−178.02 (12)
C12—N1—C1—S1	−1.79 (14)	C21—C22—C23—C24	−0.1 (2)
C11—S1—C1—N1	1.11 (10)	C2—N2—C24—C25	11.3 (2)
C11—S1—C1—C21	−177.37 (11)	C2—N2—C24—C23	−169.07 (13)
C24—N2—C2—C31	−93.43 (16)	C22—C23—C24—N2	178.90 (13)
C1—S1—C11—C16	178.94 (13)	C22—C23—C24—C25	−1.4 (2)
C1—S1—C11—C12	−0.09 (10)	N2—C24—C25—C26	−178.83 (13)
C1—N1—C12—C13	−177.24 (13)	C23—C24—C25—C26	1.5 (2)
C1—N1—C12—C11	1.72 (15)	C24—C25—C26—C21	−0.1 (2)
C16—C11—C12—N1	180.00 (12)	C22—C21—C26—C25	−1.5 (2)
S1—C11—C12—N1	−0.88 (14)	C1—C21—C26—C25	178.10 (12)
C16—C11—C12—C13	−1.0 (2)	N2—C2—C31—C36	2.59 (19)
S1—C11—C12—C13	178.14 (10)	N2—C2—C31—C32	−175.35 (11)
N1—C12—C13—C14	179.44 (13)	C36—C31—C32—O1	−177.51 (11)
C11—C12—C13—C14	0.5 (2)	C2—C31—C32—O1	0.55 (16)
C12—C13—C14—C15	0.3 (2)	C36—C31—C32—C33	−0.21 (18)
C13—C14—C15—C16	−0.8 (2)	C2—C31—C32—C33	177.85 (12)
C14—C15—C16—C11	0.3 (2)	O1—C32—C33—C34	177.58 (12)
C12—C11—C16—C15	0.5 (2)	C31—C32—C33—C34	0.49 (19)
S1—C11—C16—C15	−178.40 (11)	C32—C33—C34—C35	−0.1 (2)
N1—C1—C21—C26	−3.99 (19)	C33—C34—C35—C36	−0.5 (2)
S1—C1—C21—C26	174.33 (10)	C34—C35—C36—C31	0.8 (2)
N1—C1—C21—C22	175.56 (12)	C32—C31—C36—C35	−0.44 (19)
S1—C1—C21—C22	−6.12 (17)	C2—C31—C36—C35	−178.37 (13)
C26—C21—C22—C23	1.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.95	2.7459 (14)	164
C26—H26···O1ⁱ	0.95	2.48	3.3645 (16)	156
N2—H72···Cgⁱⁱ	0.82 (2)	2.61 (2)	3.4024 (14)	163.0 (19)

Symmetry codes: (i) −x, −y, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂OS
M_r	332.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	13.3260 (4), 5.7940 (1), 24.2246 (6)
β (°)	121.546 (1)
V (Å³)	1593.99 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.44 × 0.17 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.929, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15126, 3953, 3272
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.03
No. of reflections	3953
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SIR97 (Altomare et al., 1999), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.95	2.7459 (14)	163.6
C26—H26···O1ⁱ	0.95	2.48	3.3645 (16)	155.6
N2—H72···Cgⁱⁱ	0.82 (2)	2.61 (2)	3.4024 (14)	163.0 (19)

Symmetry codes: (i) −x, −y, −z; (ii) x, y+1, z.

Acknowledgements

The authors thank Mr Jason Kopp for helpful discussions.

References

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