2-({[4-(1,3-Benzothia-zol-2-yl)phen-yl]amino}methyl)-phenol.

In the title compound, C(20)H(16)N(2)OS, the aniline substituent essentially coplanar with the benzothia-zole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å). The phenol group is almost perpendic-ular to the benzothia-zolylaniline group, with an inter-planar angle of 88.36 (2)°. In the crystal, mol-ecules aggregate as centrosymmetric dimers by pairs of O-H⋯N hydrogen bonds. C-H⋯O contacts and N-H⋯π(arene) inter-actions 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 = 332.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.03

3953 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051580/gg2063sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811051580/gg2063Isup2.cdx

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

Supplementary material file. DOI: 10.1107/S1600536811051580/gg2063Isup4.cml

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

C20H16N2OS	F(000) = 696
Mr = 332.41	Dx = 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

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

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(Fo2) + (0.0417P)2 + 0.6757P] where P = (Fo2 + 2Fc2)/3
3953 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .