(E)-2-({[3-Benzyl­sulfan­yl-5-(p-tol­yl)-4H-1,2,4-triazol-4-yl]imino}­meth­yl)phenol

In the title compound, C₂₃H₂₀N₄OS, the 1,2,4-triazole ring (r.m.s. deviation = 0.014 Å) forms dihedral angles of 88.66 (8), 24.48 (8) and 17.97 (7)° with the benzyl, p-tolyl and phenol rings, respectively. The conformation about the C=N bond is E. In the crystal, mol­ecules are linked by O—H...N hydrogen bonds, forming chains along [010].

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.099
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  C8      ..        5.1 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.793 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

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

(E)-2-({[3-Benzylsulfanyl-5-(p-tolyl)-4H-1,2,4-triazol-4-yl]imino}methyl)phenol

Crystal data

C23H20N4OS	F(000) = 840
Mr = 400.49	Dx = 1.358 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6546 reflections
a = 11.8003 (12) Å	θ = 1.8–27.9°
b = 17.9297 (16) Å	µ = 0.19 mm^−1
c = 9.8723 (8) Å	T = 113 K
β = 110.279 (5)°	Prism, colourless
V = 1959.3 (3) Å^3	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection

Rigaku Saturn CCD area detector diffractometer	4677 independent reflections
Radiation source: rotating anode	4023 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.044
Detector resolution: 14.22 pixels mm^-1	θmax = 27.9°, θmin = 1.8°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −23→20
Tmin = 0.963, Tmax = 0.978	l = −12→12
22129 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.0691P] where P = (Fo^2 + 2Fc^2)/3
4677 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.05368 (3)	0.073331 (19)	0.84276 (4)	0.02198 (11)
O1	0.04559 (9)	−0.07904 (5)	0.64668 (11)	0.0235 (2)
H1	0.0323 (17)	−0.1309 (12)	0.657 (2)	0.053 (6)*
N1	−0.05660 (10)	0.22483 (6)	0.83583 (13)	0.0211 (3)
N2	0.00556 (10)	0.28249 (6)	0.79821 (13)	0.0201 (3)
N3	0.07357 (10)	0.17775 (6)	0.74342 (12)	0.0170 (2)
N4	0.15716 (10)	0.12969 (6)	0.71510 (12)	0.0182 (2)
C1	−0.32364 (13)	0.12819 (8)	0.76880 (16)	0.0225 (3)
H1A	−0.2946	0.1052	0.7005	0.027*
C2	−0.44007 (13)	0.15724 (8)	0.72435 (17)	0.0271 (3)
H2	−0.4902	0.1540	0.6257	0.032*
C3	−0.48351 (13)	0.19083 (9)	0.82265 (18)	0.0297 (4)
H3	−0.5635	0.2100	0.7921	0.036*
C4	−0.40971 (14)	0.19621 (9)	0.96563 (18)	0.0292 (4)
H4	−0.4388	0.2194	1.0337	0.035*
C5	−0.29371 (13)	0.16795 (8)	1.00994 (16)	0.0243 (3)
H5	−0.2431	0.1726	1.1082	0.029*
C6	−0.25002 (12)	0.13271 (7)	0.91230 (15)	0.0182 (3)
C7	−0.12538 (12)	0.09818 (8)	0.97144 (15)	0.0221 (3)
H7A	−0.1309	0.0526	1.0254	0.027*
H7B	−0.0717	0.1335	1.0418	0.027*
C8	−0.01388 (12)	0.16245 (7)	0.80360 (15)	0.0191 (3)
C9	0.08464 (12)	0.25386 (7)	0.74565 (15)	0.0174 (3)
C10	0.16945 (12)	0.29819 (7)	0.70022 (15)	0.0176 (3)
C11	0.21798 (12)	0.27415 (8)	0.59754 (15)	0.0192 (3)
H11	0.2010	0.2252	0.5589	0.023*
C12	0.29062 (12)	0.32083 (8)	0.55128 (16)	0.0215 (3)
H12	0.3224	0.3033	0.4809	0.026*
C13	0.31820 (12)	0.39299 (8)	0.60553 (16)	0.0215 (3)
C14	0.27198 (13)	0.41596 (8)	0.71107 (17)	0.0239 (3)
H14	0.2913	0.4643	0.7518	0.029*
C15	0.19875 (13)	0.37003 (8)	0.75794 (16)	0.0225 (3)
H15	0.1682	0.3873	0.8296	0.027*
C16	0.39281 (14)	0.44438 (8)	0.54910 (18)	0.0281 (3)
H16A	0.4761	0.4259	0.5793	0.042*
H16B	0.3922	0.4946	0.5879	0.042*
H16C	0.3586	0.4460	0.4434	0.042*
C17	0.11524 (12)	0.06527 (7)	0.66711 (15)	0.0184 (3)
H17	0.0323	0.0547	0.6487	0.022*
C18	0.19257 (12)	0.00785 (7)	0.64025 (14)	0.0177 (3)
C19	0.30414 (12)	0.02410 (8)	0.62744 (16)	0.0227 (3)
H19	0.3310	0.0743	0.6337	0.027*
C20	0.37576 (13)	−0.03235 (8)	0.60577 (16)	0.0259 (3)
H20	0.4515	−0.0211	0.5968	0.031*
C21	0.33616 (14)	−0.10567 (8)	0.59720 (16)	0.0257 (3)
H21	0.3859	−0.1444	0.5834	0.031*
C22	0.22584 (13)	−0.12335 (8)	0.60829 (15)	0.0217 (3)
H22	0.1994	−0.1737	0.6006	0.026*
C23	0.15335 (12)	−0.06653 (7)	0.63100 (15)	0.0185 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02314 (19)	0.01440 (19)	0.0331 (2)	0.00067 (14)	0.01575 (16)	0.00221 (14)
O1	0.0241 (5)	0.0149 (5)	0.0357 (6)	−0.0020 (4)	0.0160 (5)	0.0011 (4)
N1	0.0196 (6)	0.0157 (6)	0.0301 (7)	0.0003 (5)	0.0114 (5)	0.0013 (5)
N2	0.0202 (6)	0.0147 (6)	0.0270 (6)	0.0003 (5)	0.0102 (5)	0.0012 (5)
N3	0.0164 (5)	0.0128 (6)	0.0230 (6)	0.0013 (4)	0.0086 (5)	−0.0001 (5)
N4	0.0183 (6)	0.0149 (6)	0.0231 (6)	0.0046 (5)	0.0095 (5)	0.0007 (5)
C1	0.0259 (7)	0.0204 (7)	0.0241 (8)	−0.0021 (6)	0.0122 (6)	0.0011 (6)
C2	0.0216 (7)	0.0301 (8)	0.0269 (8)	−0.0035 (6)	0.0049 (6)	0.0070 (6)
C3	0.0193 (7)	0.0289 (8)	0.0425 (10)	0.0037 (6)	0.0126 (7)	0.0086 (7)
C4	0.0285 (8)	0.0276 (8)	0.0382 (9)	0.0022 (7)	0.0200 (7)	−0.0013 (7)
C5	0.0254 (7)	0.0248 (8)	0.0244 (8)	−0.0014 (6)	0.0108 (6)	−0.0005 (6)
C6	0.0188 (7)	0.0133 (7)	0.0244 (7)	−0.0037 (5)	0.0099 (6)	0.0025 (5)
C7	0.0221 (7)	0.0228 (7)	0.0232 (7)	0.0022 (6)	0.0100 (6)	0.0038 (6)
C8	0.0156 (6)	0.0174 (7)	0.0245 (7)	0.0011 (5)	0.0072 (6)	0.0011 (6)
C9	0.0161 (6)	0.0141 (7)	0.0211 (7)	0.0019 (5)	0.0054 (6)	0.0003 (5)
C10	0.0162 (6)	0.0154 (7)	0.0204 (7)	0.0012 (5)	0.0055 (6)	0.0028 (5)
C11	0.0202 (7)	0.0161 (7)	0.0201 (7)	0.0012 (6)	0.0054 (6)	−0.0001 (5)
C12	0.0210 (7)	0.0228 (8)	0.0221 (7)	0.0025 (6)	0.0091 (6)	0.0019 (6)
C13	0.0176 (7)	0.0207 (7)	0.0249 (8)	0.0001 (6)	0.0060 (6)	0.0038 (6)
C14	0.0243 (8)	0.0156 (7)	0.0343 (9)	−0.0026 (6)	0.0134 (7)	−0.0019 (6)
C15	0.0243 (7)	0.0183 (7)	0.0284 (8)	−0.0001 (6)	0.0136 (6)	−0.0027 (6)
C16	0.0291 (8)	0.0265 (8)	0.0328 (9)	−0.0047 (7)	0.0157 (7)	0.0007 (7)
C17	0.0180 (7)	0.0189 (7)	0.0185 (7)	0.0003 (5)	0.0068 (6)	0.0022 (5)
C18	0.0199 (7)	0.0157 (7)	0.0181 (7)	0.0010 (5)	0.0073 (6)	0.0006 (5)
C19	0.0232 (7)	0.0214 (7)	0.0251 (8)	−0.0012 (6)	0.0104 (6)	−0.0003 (6)
C20	0.0228 (7)	0.0294 (8)	0.0302 (8)	0.0023 (6)	0.0153 (7)	0.0004 (7)
C21	0.0302 (8)	0.0246 (8)	0.0262 (8)	0.0092 (6)	0.0148 (7)	0.0000 (6)
C22	0.0299 (8)	0.0161 (7)	0.0208 (7)	0.0009 (6)	0.0110 (6)	−0.0003 (6)
C23	0.0210 (7)	0.0190 (7)	0.0166 (7)	0.0000 (6)	0.0078 (6)	0.0009 (5)

Geometric parameters (Å, º)

S1—C8	1.7462 (14)	C10—C11	1.3941 (19)
S1—C7	1.8091 (14)	C10—C15	1.4025 (19)
O1—C23	1.3519 (16)	C11—C12	1.3839 (19)
O1—H1	0.95 (2)	C11—H11	0.9500
N1—C8	1.3106 (17)	C12—C13	1.395 (2)
N1—N2	1.3904 (16)	C12—H12	0.9500
N2—C9	1.3187 (17)	C13—C14	1.395 (2)
N3—C9	1.3704 (17)	C13—C16	1.508 (2)
N3—C8	1.3849 (17)	C14—C15	1.3842 (19)
N3—N4	1.4088 (15)	C14—H14	0.9500
N4—C17	1.2810 (17)	C15—H15	0.9500
C1—C6	1.3838 (19)	C16—H16A	0.9800
C1—C2	1.391 (2)	C16—H16B	0.9800
C1—H1A	0.9500	C16—H16C	0.9800
C2—C3	1.383 (2)	C17—C18	1.4597 (19)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.381 (2)	C18—C19	1.3963 (18)
C3—H3	0.9500	C18—C23	1.4042 (19)
C4—C5	1.381 (2)	C19—C20	1.382 (2)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.3923 (19)	C20—C21	1.388 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.5141 (19)	C21—C22	1.381 (2)
C7—H7A	0.9900	C21—H21	0.9500
C7—H7B	0.9900	C22—C23	1.3974 (19)
C9—C10	1.4648 (18)	C22—H22	0.9500
C8—S1—C7	99.05 (7)	C12—C11—H11	119.7
C23—O1—H1	111.8 (12)	C10—C11—H11	119.7
C8—N1—N2	106.67 (11)	C11—C12—C13	121.53 (13)
C9—N2—N1	109.05 (11)	C11—C12—H12	119.2
C9—N3—C8	105.75 (11)	C13—C12—H12	119.2
C9—N3—N4	122.88 (11)	C12—C13—C14	117.45 (13)
C8—N3—N4	129.87 (11)	C12—C13—C16	120.88 (13)
C17—N4—N3	114.69 (11)	C14—C13—C16	121.66 (13)
C6—C1—C2	120.14 (14)	C15—C14—C13	121.66 (13)
C6—C1—H1A	119.9	C15—C14—H14	119.2
C2—C1—H1A	119.9	C13—C14—H14	119.2
C3—C2—C1	120.51 (14)	C14—C15—C10	120.34 (13)
C3—C2—H2	119.7	C14—C15—H15	119.8
C1—C2—H2	119.7	C10—C15—H15	119.8
C4—C3—C2	119.46 (14)	C13—C16—H16A	109.5
C4—C3—H3	120.3	C13—C16—H16B	109.5
C2—C3—H3	120.3	H16A—C16—H16B	109.5
C5—C4—C3	120.18 (15)	C13—C16—H16C	109.5
C5—C4—H4	119.9	H16A—C16—H16C	109.5
C3—C4—H4	119.9	H16B—C16—H16C	109.5
C4—C5—C6	120.76 (14)	N4—C17—C18	121.17 (12)
C4—C5—H5	119.6	N4—C17—H17	119.4
C6—C5—H5	119.6	C18—C17—H17	119.4
C1—C6—C5	118.92 (13)	C19—C18—C23	119.48 (13)
C1—C6—C7	123.51 (13)	C19—C18—C17	122.53 (12)
C5—C6—C7	117.51 (13)	C23—C18—C17	117.97 (12)
C6—C7—S1	117.27 (10)	C20—C19—C18	120.51 (13)
C6—C7—H7A	108.0	C20—C19—H19	119.7
S1—C7—H7A	108.0	C18—C19—H19	119.7
C6—C7—H7B	108.0	C19—C20—C21	119.47 (13)
S1—C7—H7B	108.0	C19—C20—H20	120.3
H7A—C7—H7B	107.2	C21—C20—H20	120.3
N1—C8—N3	109.97 (12)	C22—C21—C20	121.30 (13)
N1—C8—S1	124.86 (11)	C22—C21—H21	119.3
N3—C8—S1	125.02 (10)	C20—C21—H21	119.3
N2—C9—N3	108.51 (12)	C21—C22—C23	119.45 (13)
N2—C9—C10	124.13 (11)	C21—C22—H22	120.3
N3—C9—C10	127.36 (12)	C23—C22—H22	120.3
C11—C10—C15	118.29 (13)	O1—C23—C22	123.35 (12)
C11—C10—C9	123.45 (12)	O1—C23—C18	116.87 (12)
C15—C10—C9	118.19 (12)	C22—C23—C18	119.77 (13)
C12—C11—C10	120.69 (13)
C8—N1—N2—C9	−0.55 (15)	N2—C9—C10—C11	−154.26 (14)
C9—N3—N4—C17	−156.47 (13)	N3—C9—C10—C11	26.5 (2)
C8—N3—N4—C17	39.60 (19)	N2—C9—C10—C15	22.5 (2)
C6—C1—C2—C3	0.0 (2)	N3—C9—C10—C15	−156.66 (14)
C1—C2—C3—C4	0.8 (2)	C15—C10—C11—C12	−1.6 (2)
C2—C3—C4—C5	−0.3 (2)	C9—C10—C11—C12	175.15 (12)
C3—C4—C5—C6	−1.0 (2)	C10—C11—C12—C13	0.2 (2)
C2—C1—C6—C5	−1.2 (2)	C11—C12—C13—C14	1.4 (2)
C2—C1—C6—C7	175.89 (13)	C11—C12—C13—C16	−177.20 (13)
C4—C5—C6—C1	1.8 (2)	C12—C13—C14—C15	−1.7 (2)
C4—C5—C6—C7	−175.54 (13)	C16—C13—C14—C15	176.88 (13)
C1—C6—C7—S1	17.78 (18)	C13—C14—C15—C10	0.4 (2)
C5—C6—C7—S1	−165.06 (11)	C11—C10—C15—C14	1.3 (2)
C8—S1—C7—C6	74.69 (11)	C9—C10—C15—C14	−175.62 (13)
N2—N1—C8—N3	−0.98 (15)	N3—N4—C17—C18	−176.57 (12)
N2—N1—C8—S1	174.78 (10)	N4—C17—C18—C19	−17.4 (2)
C9—N3—C8—N1	2.08 (16)	N4—C17—C18—C23	160.89 (13)
N4—N3—C8—N1	168.11 (12)	C23—C18—C19—C20	0.0 (2)
C9—N3—C8—S1	−173.67 (10)	C17—C18—C19—C20	178.29 (13)
N4—N3—C8—S1	−7.6 (2)	C18—C19—C20—C21	−0.2 (2)
C7—S1—C8—N1	−14.82 (14)	C19—C20—C21—C22	0.7 (2)
C7—S1—C8—N3	160.31 (12)	C20—C21—C22—C23	−1.1 (2)
N1—N2—C9—N3	1.86 (15)	C21—C22—C23—O1	−178.32 (13)
N1—N2—C9—C10	−177.46 (12)	C21—C22—C23—C18	0.9 (2)
C8—N3—C9—N2	−2.39 (15)	C19—C18—C23—O1	178.88 (12)
N4—N3—C9—N2	−169.64 (11)	C17—C18—C23—O1	0.53 (19)
C8—N3—C9—C10	176.91 (13)	C19—C18—C23—C22	−0.4 (2)
N4—N3—C9—C10	9.7 (2)	C17—C18—C23—C22	−178.72 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.95 (2)	1.72 (2)	2.6555 (15)	167.6 (19)

Symmetry code: (i) −x, y−1/2, −z+3/2.