Crystal structure of 2-{[5-(methyl­sulfan­yl)-4-phenyl-4H-1,2,4-triazol-3-yl]meth­yl}benzo[d]thia­zole

In the crystal structure of the title compound, the triazole ring exhibits inter­planar angles of ca 64 and 77° with the phenyl and benzo­thia­zole planes, respectively. The packing involves three borderline C—H...N contacts and a pairing of the triazole rings across an inversion centre.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.028
• wR factor = 0.086
• Data-to-parameter ratio = 50.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.58 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT480_ALERT_4_G Long H...A H-Bond Reported H11A     ..N3       .       2.68 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13      ..N1       .       2.68 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H14      ..N2       .       2.67 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        180 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

   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
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO 1.171.41.122a (Rigaku OD, 2021); cell refinement: CrysAlis PRO 1.171.41.122a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.41.122a (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2019/3 (Sheldrick, 2015b).

2-{[5-(Methylsulfanyl)-4-phenyl-4H-1,2,4-triazol-3-yl]methyl}benzo[d]thiazole

Crystal data

C17H14N4S2	Z = 2
Mr = 338.44	F(000) = 352
Triclinic, P1	Dx = 1.410 Mg m^−3
a = 8.9714 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3564 (3) Å	Cell parameters from 69237 reflections
c = 10.4969 (2) Å	θ = 2.3–41.4°
α = 94.088 (2)°	µ = 0.34 mm^−1
β = 105.954 (2)°	T = 100 K
γ = 107.393 (2)°	Tablet, colourless
V = 797.05 (3) Å^3	0.17 × 0.12 × 0.10 mm

Data collection

XtaLAB Synergy diffractometer	10466 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	9289 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.0000 pixels mm^-1	θmax = 41.2°, θmin = 2.1°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	k = −17→17
Tmin = 0.859, Tmax = 1.000	l = −19→19
102462 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.0903P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
10466 reflections	Δρmax = 0.66 e Å^−3
209 parameters	Δρmin = −0.25 e Å^−3
0 restraints

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.6560 (0.0019) x - 4.9080 (0.0018) y + 9.3027 (0.0011) z = 3.1483 (0.0010)

* -0.0006 (0.0003) C12 * 0.0030 (0.0004) C13 * -0.0029 (0.0004) C14 * 0.0003 (0.0004) C15 * 0.0021 (0.0004) C16 * -0.0019 (0.0003) C17 0.0217 (0.0007) N4

Rms deviation of fitted atoms = 0.0021

2.6765 (0.0019) x + 7.5840 (0.0013) y - 0.9757 (0.0024) z = 2.4430 (0.0013)

Angle to previous plane (with approximate esd) = 63.863 ( 0.019 )

* -0.0001 (0.0003) N1 * 0.0018 (0.0003) N2 * 0.0025 (0.0002) N4 * -0.0014 (0.0003) C9 * -0.0027 (0.0003) C10 -0.0058 (0.0008) C8 -0.0865 (0.0007) C12 0.0346 (0.0007) S2

Rms deviation of fitted atoms = 0.0019

5.3893 (0.0012) x - 6.3624 (0.0008) y + 5.1564 (0.0013) z = 5.5973 (0.0010)

Angle to previous plane (with approximate esd) = 76.957 ( 0.014 )

* -0.0079 (0.0003) S1 * 0.0083 (0.0003) C2 * -0.0011 (0.0004) N3 * 0.0009 (0.0004) C3A * -0.0081 (0.0005) C4 * 0.0025 (0.0005) C5 * 0.0038 (0.0005) C6 * -0.0013 (0.0004) C7 * 0.0028 (0.0004) C7A 0.0979 (0.0006) C8

Rms deviation of fitted atoms = 0.0050

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.86054 (2)	0.48129 (2)	0.77843 (2)	0.01557 (3)
S2	0.40521 (2)	0.21180 (2)	0.21857 (2)	0.01692 (3)
N1	0.69326 (5)	0.14743 (5)	0.54398 (4)	0.01461 (6)
N2	0.64593 (5)	0.14656 (5)	0.40548 (4)	0.01439 (6)
N3	0.65416 (5)	0.41599 (5)	0.91486 (4)	0.01501 (6)
N4	0.47354 (4)	0.21828 (4)	0.48932 (4)	0.01123 (5)
C2	0.68997 (5)	0.36293 (5)	0.81379 (5)	0.01319 (6)
C3A	0.76637 (6)	0.55937 (6)	0.97489 (5)	0.01493 (7)
C4	0.76214 (7)	0.64760 (7)	1.08644 (6)	0.02094 (9)
H4	0.678550	0.611765	1.127062	0.025*
C5	0.88296 (8)	0.78864 (7)	1.13624 (6)	0.02484 (10)
H5	0.882744	0.849356	1.212644	0.030*
C6	1.00541 (8)	0.84304 (7)	1.07564 (7)	0.02362 (10)
H6	1.086509	0.940173	1.111582	0.028*
C7	1.01035 (7)	0.75745 (6)	0.96388 (6)	0.02010 (9)
H7	1.092893	0.794830	0.922535	0.024*
C7A	0.88963 (6)	0.61445 (5)	0.91440 (5)	0.01491 (7)
C8	0.59619 (6)	0.20550 (5)	0.73494 (5)	0.01490 (7)
H8A	0.647569	0.133827	0.778009	0.018*
H8B	0.482421	0.175752	0.739460	0.018*
C9	0.58961 (5)	0.18991 (5)	0.59118 (5)	0.01228 (6)
C10	0.51471 (5)	0.18851 (5)	0.37612 (5)	0.01212 (6)
C11	0.54143 (10)	0.18497 (8)	0.12746 (7)	0.02628 (11)
H11A	0.500730	0.200775	0.034712	0.039*
H11B	0.545540	0.081470	0.127332	0.039*
H11C	0.651920	0.258121	0.170908	0.039*
C12	0.33320 (5)	0.25713 (5)	0.49752 (5)	0.01169 (6)
C13	0.17638 (6)	0.15400 (5)	0.43243 (6)	0.01604 (7)
H13	0.162422	0.059676	0.382357	0.019*
C14	0.04025 (6)	0.19174 (6)	0.44212 (6)	0.01850 (8)
H14	−0.067511	0.123172	0.397683	0.022*
C15	0.06206 (6)	0.32983 (6)	0.51686 (6)	0.01743 (8)
H15	−0.030950	0.354811	0.523584	0.021*
C16	0.21950 (6)	0.43126 (6)	0.58166 (5)	0.01627 (7)
H16	0.233522	0.525098	0.632575	0.020*
C17	0.35680 (6)	0.39572 (5)	0.57216 (5)	0.01364 (7)
H17	0.464502	0.464813	0.615821	0.016*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01412 (5)	0.01676 (5)	0.01501 (5)	0.00285 (4)	0.00577 (4)	0.00253 (4)
S2	0.01817 (5)	0.01874 (5)	0.01337 (5)	0.00661 (4)	0.00344 (4)	0.00346 (4)
N1	0.01107 (13)	0.01546 (14)	0.01739 (16)	0.00585 (11)	0.00320 (12)	0.00174 (12)
N2	0.01163 (13)	0.01526 (14)	0.01706 (16)	0.00536 (11)	0.00506 (12)	0.00130 (12)
N3	0.01422 (14)	0.01645 (15)	0.01332 (15)	0.00367 (12)	0.00428 (12)	0.00227 (12)
N4	0.00944 (12)	0.01239 (13)	0.01242 (14)	0.00476 (10)	0.00313 (10)	0.00170 (10)
C2	0.01226 (15)	0.01421 (15)	0.01189 (15)	0.00350 (12)	0.00266 (12)	0.00293 (12)
C3A	0.01476 (16)	0.01592 (16)	0.01294 (16)	0.00514 (13)	0.00257 (13)	0.00182 (13)
C4	0.0226 (2)	0.0228 (2)	0.01640 (19)	0.00840 (18)	0.00479 (17)	−0.00129 (16)
C5	0.0265 (2)	0.0221 (2)	0.0212 (2)	0.00883 (19)	0.00129 (19)	−0.00446 (18)
C6	0.0222 (2)	0.01629 (19)	0.0242 (2)	0.00439 (17)	−0.00227 (18)	−0.00112 (17)
C7	0.01646 (18)	0.01581 (18)	0.0226 (2)	0.00197 (14)	0.00139 (16)	0.00295 (16)
C7A	0.01367 (16)	0.01456 (16)	0.01459 (17)	0.00406 (13)	0.00200 (13)	0.00291 (13)
C8	0.01522 (16)	0.01389 (15)	0.01334 (16)	0.00301 (13)	0.00283 (13)	0.00258 (12)
C9	0.01024 (14)	0.01221 (14)	0.01353 (16)	0.00399 (11)	0.00216 (12)	0.00169 (12)
C10	0.01095 (14)	0.01190 (14)	0.01336 (16)	0.00363 (11)	0.00398 (12)	0.00119 (12)
C11	0.0363 (3)	0.0289 (3)	0.0200 (2)	0.0127 (2)	0.0159 (2)	0.00653 (19)
C12	0.00982 (13)	0.01180 (14)	0.01430 (16)	0.00444 (11)	0.00418 (12)	0.00211 (12)
C13	0.01030 (14)	0.01344 (16)	0.0229 (2)	0.00391 (12)	0.00377 (14)	−0.00030 (14)
C14	0.01035 (15)	0.01583 (17)	0.0290 (2)	0.00453 (13)	0.00582 (15)	0.00189 (16)
C15	0.01381 (16)	0.01674 (17)	0.0259 (2)	0.00773 (14)	0.00937 (16)	0.00506 (15)
C16	0.01628 (17)	0.01471 (16)	0.0206 (2)	0.00720 (14)	0.00803 (15)	0.00189 (14)
C17	0.01255 (15)	0.01250 (15)	0.01612 (17)	0.00444 (12)	0.00489 (13)	0.00105 (12)

Geometric parameters (Å, º)

S1—C7A	1.7334 (5)	C12—C17	1.3928 (6)
S1—C2	1.7503 (5)	C12—C13	1.3940 (6)
S2—C10	1.7418 (5)	C13—C14	1.3955 (7)
S2—C11	1.8063 (6)	C14—C15	1.3939 (7)
N1—C9	1.3094 (6)	C15—C16	1.3917 (7)
N1—N2	1.3968 (6)	C16—C17	1.3948 (6)
N2—C10	1.3150 (6)	C4—H4	0.9500
N3—C2	1.2973 (6)	C5—H5	0.9500
N3—C3A	1.3905 (7)	C6—H6	0.9500
N4—C10	1.3716 (6)	C7—H7	0.9500
N4—C9	1.3754 (6)	C8—H8A	0.9900
N4—C12	1.4330 (5)	C8—H8B	0.9900
C2—C8	1.5050 (7)	C11—H11A	0.9800
C3A—C4	1.3997 (7)	C11—H11B	0.9800
C3A—C7A	1.4084 (7)	C11—H11C	0.9800
C4—C5	1.3873 (9)	C13—H13	0.9500
C5—C6	1.4023 (10)	C14—H14	0.9500
C6—C7	1.3912 (9)	C15—H15	0.9500
C7—C7A	1.3994 (7)	C16—H16	0.9500
C8—C9	1.4887 (7)	C17—H17	0.9500
C7A—S1—C2	88.86 (2)	C16—C15—C14	120.28 (4)
C10—S2—C11	98.33 (3)	C15—C16—C17	120.28 (4)
C9—N1—N2	107.60 (4)	C12—C17—C16	118.83 (4)
C10—N2—N1	106.63 (4)	C5—C4—H4	120.8
C2—N3—C3A	110.40 (4)	C3A—C4—H4	120.8
C10—N4—C9	104.30 (4)	C4—C5—H5	119.5
C10—N4—C12	127.66 (4)	C6—C5—H5	119.5
C9—N4—C12	127.84 (4)	C7—C6—H6	119.4
N3—C2—C8	122.28 (4)	C5—C6—H6	119.4
N3—C2—S1	116.30 (4)	C6—C7—H7	121.1
C8—C2—S1	121.35 (3)	C7A—C7—H7	121.1
N3—C3A—C4	124.68 (5)	C9—C8—H8A	108.7
N3—C3A—C7A	115.00 (4)	C2—C8—H8A	108.7
C4—C3A—C7A	120.32 (5)	C9—C8—H8B	108.7
C5—C4—C3A	118.40 (6)	C2—C8—H8B	108.7
C4—C5—C6	121.08 (6)	H8A—C8—H8B	107.6
C7—C6—C5	121.24 (5)	S2—C11—H11A	109.5
C6—C7—C7A	117.76 (5)	S2—C11—H11B	109.5
C7—C7A—C3A	121.20 (5)	H11A—C11—H11B	109.5
C7—C7A—S1	129.37 (4)	S2—C11—H11C	109.5
C3A—C7A—S1	109.43 (3)	H11A—C11—H11C	109.5
C9—C8—C2	114.28 (4)	H11B—C11—H11C	109.5
N1—C9—N4	110.51 (4)	C12—C13—H13	120.6
N1—C9—C8	124.86 (4)	C14—C13—H13	120.6
N4—C9—C8	124.63 (4)	C15—C14—H14	119.9
N2—C10—N4	110.97 (4)	C13—C14—H14	119.9
N2—C10—S2	126.93 (4)	C16—C15—H15	119.9
N4—C10—S2	122.07 (3)	C14—C15—H15	119.9
C17—C12—C13	121.63 (4)	C15—C16—H16	119.9
C17—C12—N4	119.25 (4)	C17—C16—H16	119.9
C13—C12—N4	119.12 (4)	C12—C17—H17	120.6
C12—C13—C14	118.84 (4)	C16—C17—H17	120.6
C15—C14—C13	120.14 (5)
C9—N1—N2—C10	−0.19 (5)	C12—N4—C9—N1	175.49 (4)
C3A—N3—C2—C8	175.98 (4)	C10—N4—C9—C8	−179.64 (4)
C3A—N3—C2—S1	−1.04 (5)	C12—N4—C9—C8	−4.54 (7)
C7A—S1—C2—N3	1.07 (4)	C2—C8—C9—N1	93.15 (6)
C7A—S1—C2—C8	−175.98 (4)	C2—C8—C9—N4	−86.82 (5)
C2—N3—C3A—C4	179.97 (5)	N1—N2—C10—N4	0.44 (5)
C2—N3—C3A—C7A	0.43 (6)	N1—N2—C10—S2	178.46 (3)
N3—C3A—C4—C5	179.66 (5)	C9—N4—C10—N2	−0.51 (5)
C7A—C3A—C4—C5	−0.82 (8)	C12—N4—C10—N2	−175.63 (4)
C3A—C4—C5—C6	0.86 (9)	C9—N4—C10—S2	−178.64 (3)
C4—C5—C6—C7	−0.20 (10)	C12—N4—C10—S2	6.24 (6)
C5—C6—C7—C7A	−0.49 (9)	C11—S2—C10—N2	−6.70 (5)
C6—C7—C7A—C3A	0.52 (8)	C11—S2—C10—N4	171.12 (4)
C6—C7—C7A—S1	179.73 (4)	C10—N4—C12—C17	−119.71 (5)
N3—C3A—C7A—C7	179.70 (5)	C9—N4—C12—C17	66.28 (6)
C4—C3A—C7A—C7	0.13 (8)	C10—N4—C12—C13	61.39 (6)
N3—C3A—C7A—S1	0.35 (5)	C9—N4—C12—C13	−112.62 (5)
C4—C3A—C7A—S1	−179.22 (4)	C17—C12—C13—C14	0.38 (8)
C2—S1—C7A—C7	179.99 (5)	N4—C12—C13—C14	179.25 (5)
C2—S1—C7A—C3A	−0.73 (4)	C12—C13—C14—C15	−0.59 (8)
N3—C2—C8—C9	149.86 (5)	C13—C14—C15—C16	0.35 (9)
S1—C2—C8—C9	−33.27 (6)	C14—C15—C16—C17	0.12 (8)
N2—N1—C9—N4	−0.13 (5)	C13—C12—C17—C16	0.08 (7)
N2—N1—C9—C8	179.90 (4)	N4—C12—C17—C16	−178.79 (4)
C10—N4—C9—N1	0.39 (5)	C15—C16—C17—C12	−0.33 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···N3^i	0.98	2.68	3.3610 (8)	127
C13—H13···N1^ii	0.95	2.68	3.3609 (6)	129
C14—H14···N2^iii	0.95	2.67	3.3431 (6)	129

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