2-[(3-Propyl-sulfanyl-5-p-tolyl-4H-1,2,4-triazol-4-yl)imino-meth-yl]phenol.

In the title mol-ecule, C(19)H(20)N(4)OS, the two benzene rings form dihedral angles of 16.2 (1) and 12.0 (1)°, respectively, with the central triazole ring. In the crystal, inter-molecular O-H⋯N hydrogen bonds link mol-ecules into chains in the [010] direction.

Related literature

For standard values of the bond lengths, see: Allen et al. (1987 ▶). For the crystal structure of a related compound, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C19H20N4OS

M = 352.45

Monoclinic,

a = 22.682 (2) Å

b = 18.1736 (15) Å

c = 9.1557 (8) Å

β = 109.678 (7)°

V = 3553.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.962, T max = 0.977

16201 measured reflections

3499 independent reflections

3206 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.122

S = 1.14

3499 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029849/cv5131sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029849/cv5131Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029849/cv5131Isup3.cml

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

C19H20N4OS	F(000) = 1488
Mr = 352.45	Dx = 1.318 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5676 reflections
a = 22.682 (2) Å	θ = 1.9–27.9°
b = 18.1736 (15) Å	µ = 0.20 mm−1
c = 9.1557 (8) Å	T = 113 K
β = 109.678 (7)°	Prism, colourless
V = 3553.7 (5) Å3	0.20 × 0.16 × 0.12 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	3499 independent reflections
Radiation source: rotating anode	3206 reflections with I > 2σ(I)
multilayer	Rint = 0.061
Detector resolution: 14.22 pixels mm-1	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −27→27
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −21→22
Tmin = 0.962, Tmax = 0.977	l = −11→11
16201 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0382P)2 + 4.5494P] where P = (Fo2 + 2Fc2)/3
3499 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 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	0.28535 (3)	0.18666 (3)	0.66027 (7)	0.02339 (18)
O1	0.22719 (7)	0.34890 (9)	0.84176 (19)	0.0231 (4)
H1	0.2327 (15)	0.3982 (19)	0.816 (4)	0.065 (11)*
N1	0.28721 (9)	0.03831 (11)	0.6965 (2)	0.0231 (5)
N2	0.25373 (9)	−0.01562 (11)	0.7421 (2)	0.0234 (5)
N3	0.21532 (9)	0.09105 (10)	0.7742 (2)	0.0190 (4)
N4	0.17143 (9)	0.14097 (10)	0.7951 (2)	0.0206 (4)
C1	0.43083 (12)	0.09850 (16)	0.5327 (3)	0.0357 (7)
H1A	0.4081	0.0552	0.4785	0.053*
H1B	0.4737	0.0844	0.5946	0.053*
H1C	0.4320	0.1359	0.4566	0.053*
C2	0.39763 (11)	0.12982 (14)	0.6392 (3)	0.0257 (6)
H2A	0.3961	0.0919	0.7156	0.031*
H2B	0.4215	0.1725	0.6969	0.031*
C3	0.33133 (11)	0.15388 (13)	0.5455 (3)	0.0240 (5)
H3A	0.3092	0.1118	0.4819	0.029*
H3B	0.3337	0.1935	0.4735	0.029*
C4	0.26334 (10)	0.10185 (12)	0.7148 (3)	0.0194 (5)
C5	0.21029 (11)	0.01597 (12)	0.7866 (3)	0.0196 (5)
C6	0.16446 (11)	−0.02466 (13)	0.8370 (3)	0.0227 (5)
C7	0.12894 (12)	0.00694 (14)	0.9178 (3)	0.0268 (6)
H7	0.1336	0.0578	0.9433	0.032*
C8	0.08665 (12)	−0.03538 (15)	0.9615 (3)	0.0312 (6)
H8	0.0623	−0.0126	1.0152	0.037*
C9	0.07908 (11)	−0.11011 (14)	0.9288 (3)	0.0299 (6)
C10	0.11503 (12)	−0.14132 (14)	0.8479 (3)	0.0321 (6)
H10	0.1106	−0.1923	0.8234	0.038*
C11	0.15695 (11)	−0.09988 (13)	0.8024 (3)	0.0277 (6)
H11	0.1808	−0.1226	0.7473	0.033*
C12	0.03444 (13)	−0.15614 (17)	0.9807 (3)	0.0410 (7)
H12A	0.0174	−0.1957	0.9055	0.061*
H12B	0.0001	−0.1251	0.9875	0.061*
H12C	0.0568	−0.1775	1.0827	0.061*
C13	0.19299 (11)	0.20586 (13)	0.8382 (3)	0.0207 (5)
H13	0.2355	0.2165	0.8521	0.025*
C14	0.15332 (11)	0.26319 (13)	0.8662 (3)	0.0199 (5)
C15	0.09753 (11)	0.24755 (14)	0.8943 (3)	0.0256 (5)
H15	0.0839	0.1980	0.8929	0.031*
C16	0.06239 (12)	0.30375 (14)	0.9239 (3)	0.0300 (6)
H16	0.0247	0.2930	0.9434	0.036*
C17	0.08210 (12)	0.37635 (14)	0.9251 (3)	0.0283 (6)
H17	0.0574	0.4149	0.9448	0.034*
C18	0.13694 (11)	0.39332 (13)	0.8982 (3)	0.0228 (5)
H18	0.1501	0.4430	0.8997	0.027*
C19	0.17279 (11)	0.33639 (13)	0.8688 (3)	0.0200 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0284 (3)	0.0148 (3)	0.0310 (3)	−0.0006 (2)	0.0153 (3)	0.0012 (2)
O1	0.0262 (9)	0.0155 (9)	0.0319 (9)	0.0002 (7)	0.0153 (8)	0.0028 (7)
N1	0.0248 (11)	0.0157 (10)	0.0317 (11)	0.0003 (8)	0.0134 (9)	0.0030 (9)
N2	0.0256 (11)	0.0168 (10)	0.0300 (11)	−0.0006 (8)	0.0121 (9)	0.0008 (9)
N3	0.0205 (10)	0.0145 (10)	0.0235 (10)	0.0028 (8)	0.0093 (8)	−0.0001 (8)
N4	0.0222 (10)	0.0164 (10)	0.0252 (10)	0.0028 (8)	0.0108 (8)	0.0001 (8)
C1	0.0310 (15)	0.0409 (17)	0.0403 (16)	0.0033 (12)	0.0189 (13)	−0.0005 (13)
C2	0.0261 (13)	0.0246 (13)	0.0277 (13)	−0.0015 (10)	0.0108 (11)	−0.0009 (11)
C3	0.0277 (13)	0.0195 (13)	0.0274 (12)	−0.0009 (10)	0.0126 (11)	0.0021 (10)
C4	0.0210 (12)	0.0156 (12)	0.0218 (11)	−0.0009 (9)	0.0073 (10)	0.0002 (9)
C5	0.0219 (12)	0.0136 (11)	0.0229 (11)	0.0015 (9)	0.0070 (10)	0.0000 (9)
C6	0.0227 (12)	0.0188 (12)	0.0262 (12)	0.0002 (10)	0.0075 (10)	0.0069 (10)
C7	0.0330 (14)	0.0230 (13)	0.0274 (13)	0.0010 (11)	0.0140 (11)	0.0038 (11)
C8	0.0301 (14)	0.0366 (15)	0.0298 (13)	0.0002 (12)	0.0139 (11)	0.0059 (12)
C9	0.0250 (14)	0.0299 (15)	0.0322 (14)	−0.0059 (11)	0.0063 (11)	0.0107 (12)
C10	0.0265 (14)	0.0203 (13)	0.0462 (16)	−0.0027 (11)	0.0079 (12)	0.0056 (12)
C11	0.0250 (13)	0.0200 (13)	0.0377 (14)	0.0004 (10)	0.0099 (11)	0.0037 (11)
C12	0.0327 (16)	0.0453 (18)	0.0445 (17)	−0.0104 (13)	0.0125 (13)	0.0141 (14)
C13	0.0235 (12)	0.0190 (12)	0.0201 (11)	0.0002 (10)	0.0081 (10)	0.0014 (9)
C14	0.0238 (12)	0.0179 (12)	0.0186 (11)	0.0010 (9)	0.0079 (9)	0.0005 (9)
C15	0.0279 (13)	0.0201 (13)	0.0322 (13)	−0.0020 (10)	0.0145 (11)	−0.0018 (11)
C16	0.0297 (14)	0.0246 (14)	0.0428 (15)	−0.0012 (11)	0.0217 (12)	−0.0028 (12)
C17	0.0306 (14)	0.0240 (13)	0.0340 (14)	0.0053 (11)	0.0159 (12)	−0.0007 (11)
C18	0.0283 (13)	0.0169 (12)	0.0251 (12)	−0.0004 (10)	0.0115 (10)	0.0002 (10)
C19	0.0239 (12)	0.0199 (12)	0.0177 (11)	−0.0005 (10)	0.0088 (9)	0.0007 (10)

S1—C4	1.744 (2)	C7—H7	0.9500
S1—C3	1.812 (2)	C8—C9	1.389 (4)
O1—C19	1.357 (3)	C8—H8	0.9500
O1—H1	0.95 (3)	C9—C10	1.394 (4)
N1—C4	1.310 (3)	C9—C12	1.508 (3)
N1—N2	1.388 (3)	C10—C11	1.382 (3)
N2—C5	1.318 (3)	C10—H10	0.9500
N3—C5	1.377 (3)	C11—H11	0.9500
N3—C4	1.386 (3)	C12—H12A	0.9800
N3—N4	1.407 (3)	C12—H12B	0.9800
N4—C13	1.287 (3)	C12—H12C	0.9800
C1—C2	1.529 (3)	C13—C14	1.455 (3)
C1—H1A	0.9800	C13—H13	0.9500
C1—H1B	0.9800	C14—C19	1.399 (3)
C1—H1C	0.9800	C14—C15	1.403 (3)
C2—C3	1.523 (3)	C15—C16	1.377 (3)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—C17	1.392 (3)
C3—H3A	0.9900	C16—H16	0.9500
C3—H3B	0.9900	C17—C18	1.382 (3)
C5—C6	1.470 (3)	C17—H17	0.9500
C6—C7	1.388 (3)	C18—C19	1.397 (3)
C6—C11	1.401 (3)	C18—H18	0.9500
C7—C8	1.390 (3)
C4—S1—C3	98.71 (11)	C9—C8—H8	119.1
C19—O1—H1	114 (2)	C7—C8—H8	119.1
C4—N1—N2	107.00 (19)	C8—C9—C10	117.4 (2)
C5—N2—N1	109.10 (19)	C8—C9—C12	121.5 (3)
C5—N3—C4	105.69 (18)	C10—C9—C12	121.1 (2)
C5—N3—N4	123.09 (18)	C11—C10—C9	121.6 (2)
C4—N3—N4	130.37 (19)	C11—C10—H10	119.2
C13—N4—N3	114.81 (19)	C9—C10—H10	119.2
C2—C1—H1A	109.5	C10—C11—C6	120.5 (2)
C2—C1—H1B	109.5	C10—C11—H11	119.8
H1A—C1—H1B	109.5	C6—C11—H11	119.8
C2—C1—H1C	109.5	C9—C12—H12A	109.5
H1A—C1—H1C	109.5	C9—C12—H12B	109.5
H1B—C1—H1C	109.5	H12A—C12—H12B	109.5
C3—C2—C1	110.6 (2)	C9—C12—H12C	109.5
C3—C2—H2A	109.5	H12A—C12—H12C	109.5
C1—C2—H2A	109.5	H12B—C12—H12C	109.5
C3—C2—H2B	109.5	N4—C13—C14	121.1 (2)
C1—C2—H2B	109.5	N4—C13—H13	119.4
H2A—C2—H2B	108.1	C14—C13—H13	119.4
C2—C3—S1	114.79 (17)	C19—C14—C15	119.3 (2)
C2—C3—H3A	108.6	C19—C14—C13	118.3 (2)
S1—C3—H3A	108.6	C15—C14—C13	122.5 (2)
C2—C3—H3B	108.6	C16—C15—C14	120.2 (2)
S1—C3—H3B	108.6	C16—C15—H15	119.9
H3A—C3—H3B	107.5	C14—C15—H15	119.9
N1—C4—N3	109.80 (19)	C15—C16—C17	119.9 (2)
N1—C4—S1	124.89 (18)	C15—C16—H16	120.0
N3—C4—S1	125.18 (17)	C17—C16—H16	120.0
N2—C5—N3	108.4 (2)	C18—C17—C16	121.1 (2)
N2—C5—C6	124.0 (2)	C18—C17—H17	119.5
N3—C5—C6	127.6 (2)	C16—C17—H17	119.5
C7—C6—C11	118.4 (2)	C17—C18—C19	119.1 (2)
C7—C6—C5	123.9 (2)	C17—C18—H18	120.4
C11—C6—C5	117.7 (2)	C19—C18—H18	120.4
C6—C7—C8	120.4 (2)	O1—C19—C18	122.4 (2)
C6—C7—H7	119.8	O1—C19—C14	117.2 (2)
C8—C7—H7	119.8	C18—C19—C14	120.4 (2)
C9—C8—C7	121.8 (2)
C4—N1—N2—C5	0.2 (3)	C5—C6—C7—C8	−179.9 (2)
C5—N3—N4—C13	154.6 (2)	C6—C7—C8—C9	1.0 (4)
C4—N3—N4—C13	−37.5 (3)	C7—C8—C9—C10	−0.9 (4)
C1—C2—C3—S1	176.26 (18)	C7—C8—C9—C12	178.2 (2)
C4—S1—C3—C2	−80.05 (19)	C8—C9—C10—C11	0.4 (4)
N2—N1—C4—N3	1.0 (3)	C12—C9—C10—C11	−178.8 (2)
N2—N1—C4—S1	−175.07 (16)	C9—C10—C11—C6	0.0 (4)
C5—N3—C4—N1	−1.8 (2)	C7—C6—C11—C10	0.0 (4)
N4—N3—C4—N1	−171.2 (2)	C5—C6—C11—C10	179.4 (2)
C5—N3—C4—S1	174.29 (17)	N3—N4—C13—C14	−179.28 (19)
N4—N3—C4—S1	4.8 (3)	N4—C13—C14—C19	−161.9 (2)
C3—S1—C4—N1	11.7 (2)	N4—C13—C14—C15	19.7 (3)
C3—S1—C4—N3	−163.77 (19)	C19—C14—C15—C16	0.1 (4)
N1—N2—C5—N3	−1.3 (3)	C13—C14—C15—C16	178.4 (2)
N1—N2—C5—C6	177.6 (2)	C14—C15—C16—C17	0.3 (4)
C4—N3—C5—N2	1.9 (2)	C15—C16—C17—C18	−0.5 (4)
N4—N3—C5—N2	172.28 (19)	C16—C17—C18—C19	0.3 (4)
C4—N3—C5—C6	−177.0 (2)	C17—C18—C19—O1	−179.8 (2)
N4—N3—C5—C6	−6.6 (4)	C17—C18—C19—C14	0.2 (3)
N2—C5—C6—C7	164.0 (2)	C15—C14—C19—O1	179.7 (2)
N3—C5—C6—C7	−17.3 (4)	C13—C14—C19—O1	1.2 (3)
N2—C5—C6—C11	−15.3 (3)	C15—C14—C19—C18	−0.3 (3)
N3—C5—C6—C11	163.4 (2)	C13—C14—C19—C18	−178.7 (2)
C11—C6—C7—C8	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.95 (3)	2.58 (3)	3.464 (3)	155 (3)
O1—H1···N2i	0.95 (3)	1.71 (3)	2.658 (2)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.95 (3)	1.71 (3)	2.658 (2)	175 (3)

Symmetry code: (i) .