5-Methyl-1-(4-methyl­phen­yl)-N′-[1-(thio­phen-2-yl)ethyl­idene]-1H-1,2,3-triazole-4-carbohydrazide

The asymmetric unit comprises a single mol­ecule of C₁₇H₁₇N₅OS with twist angles between the planes through the thio­phenyl, methyl­triazolyl and tolyl groups of 12.3 (1) and 44.9 (1)°, respectively. A possible weak intra­molecular hydrogen bond forms between the methyl substituent on the triazole ring and the adjacent carbonyl O atom. In the crystal structure, π–π inter­actions occur between phenyl rings of pairs of mol­ecules related by inversion symmetry with a centroid–centroid separation of 3.7647 (18) Å. The shortest inter­molecular hydrogen bonding contact is a C—H...O inter­action that generates inversion dimers.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.174
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0042 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C17 H17 N5 O S
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.038 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        765 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012), and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

5-Methyl-1-(4-methylphenyl)-N'-[1-(thiophen-2-yl)ethylidene]-1H-1,2,3-triazole-4-carbohydrazide

Crystal data

C17H17N5OS	Z = 2
Mr = 339.41	F(000) = 356
Triclinic, P1	Dx = 1.329 Mg m^−3
a = 9.0292 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.864 (1) Å	Cell parameters from 1876 reflections
c = 10.8754 (9) Å	θ = 4.2–26.3°
α = 111.021 (9)°	µ = 0.21 mm^−1
β = 105.103 (8)°	T = 296 K
γ = 96.945 (7)°	Plate, colourless
V = 847.86 (14) Å^3	0.43 × 0.18 × 0.02 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas diffractometer	2493 reflections with I > 2σ(I)
ω scans	Rint = 0.032
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	θmax = 29.6°, θmin = 3.3°
Tmin = 0.690, Tmax = 1.000	h = −11→11
7552 measured reflections	k = −13→11
3957 independent reflections	l = −13→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0711P)^2 + 0.2305P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3957 reflections	Δρmax = 0.27 e Å^−3
220 parameters	Δρmin = −0.32 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.

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

	x	y	z	Uiso*/Ueq
C1	0.1112 (3)	0.4156 (4)	0.3425 (4)	0.0601 (8)
H1	0.122378	0.438200	0.435658	0.072*
C2	−0.0111 (4)	0.3116 (4)	0.2339 (4)	0.0658 (9)
H2	−0.092623	0.254289	0.244511	0.079*
C3	−0.0012 (3)	0.2998 (3)	0.1034 (3)	0.0558 (8)
H3	−0.075280	0.233982	0.018406	0.067*
C4	0.1312 (3)	0.3974 (3)	0.1160 (3)	0.0434 (6)
C5	0.1775 (3)	0.4220 (3)	0.0050 (3)	0.0429 (6)
C6	0.0912 (3)	0.3171 (3)	−0.1446 (3)	0.0584 (8)
H6A	0.055984	0.373559	−0.197589	0.088*
H6B	0.001658	0.249516	−0.149553	0.088*
H6C	0.160803	0.261177	−0.182098	0.088*
C7	0.4505 (3)	0.6844 (3)	−0.0240 (3)	0.0421 (6)
C8	0.4679 (3)	0.7032 (3)	−0.1488 (3)	0.0404 (6)
C9	0.5722 (3)	0.8129 (3)	−0.1543 (3)	0.0399 (6)
C10	0.7022 (3)	0.9388 (3)	−0.0437 (3)	0.0539 (7)
H10A	0.791056	0.948232	−0.075463	0.081*
H10B	0.732737	0.919721	0.038836	0.081*
H10C	0.666715	1.029832	−0.022930	0.081*
C11	0.6040 (3)	0.8528 (3)	−0.3642 (3)	0.0396 (6)
C12	0.6343 (3)	0.7657 (3)	−0.4820 (3)	0.0473 (7)
H12	0.611736	0.662164	−0.513414	0.057*
C13	0.6987 (3)	0.8351 (3)	−0.5525 (3)	0.0567 (8)
H13	0.717677	0.776617	−0.632754	0.068*
C14	0.7358 (3)	0.9890 (3)	−0.5071 (3)	0.0512 (7)
C15	0.7021 (3)	1.0733 (3)	−0.3892 (3)	0.0520 (7)
H15	0.725550	1.176941	−0.357128	0.062*
C16	0.6344 (3)	1.0064 (3)	−0.3184 (3)	0.0464 (6)
H16	0.609748	1.063996	−0.241044	0.056*
C17	0.8067 (4)	1.0635 (4)	−0.5852 (4)	0.0730 (10)
H17A	0.803269	1.166931	−0.551180	0.110*
H17B	0.747381	1.014761	−0.682920	0.110*
H17C	0.914343	1.056050	−0.571143	0.110*
N1	0.2922 (2)	0.5357 (2)	0.0459 (2)	0.0451 (5)
N2	0.3362 (2)	0.5630 (2)	−0.0562 (2)	0.0473 (6)
H2A	0.290362	0.502099	−0.141972	0.057*
N3	0.3746 (2)	0.6096 (2)	−0.2804 (2)	0.0472 (6)
N4	0.4142 (3)	0.6548 (2)	−0.3689 (2)	0.0482 (6)
N5	0.5345 (2)	0.7799 (2)	−0.2928 (2)	0.0409 (5)
O1	0.5302 (2)	0.7712 (2)	0.0941 (2)	0.0595 (6)
S1	0.24161 (8)	0.49989 (8)	0.28844 (8)	0.0522 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0675 (19)	0.076 (2)	0.056 (2)	0.0198 (16)	0.0326 (16)	0.0388 (17)
C2	0.0576 (18)	0.078 (2)	0.072 (2)	0.0041 (16)	0.0295 (17)	0.0404 (19)
C3	0.0497 (15)	0.0606 (18)	0.055 (2)	0.0010 (13)	0.0169 (14)	0.0255 (16)
C4	0.0449 (14)	0.0430 (14)	0.0450 (16)	0.0106 (11)	0.0177 (12)	0.0188 (12)
C5	0.0432 (14)	0.0444 (15)	0.0435 (16)	0.0108 (11)	0.0164 (12)	0.0190 (12)
C6	0.0608 (17)	0.0615 (18)	0.0431 (18)	0.0035 (14)	0.0146 (14)	0.0157 (15)
C7	0.0494 (14)	0.0451 (15)	0.0360 (16)	0.0141 (11)	0.0199 (12)	0.0162 (12)
C8	0.0453 (13)	0.0402 (14)	0.0364 (15)	0.0092 (10)	0.0169 (11)	0.0142 (11)
C9	0.0463 (13)	0.0399 (14)	0.0350 (15)	0.0118 (11)	0.0151 (11)	0.0154 (11)
C10	0.0639 (17)	0.0500 (16)	0.0406 (17)	0.0021 (13)	0.0122 (14)	0.0175 (13)
C11	0.0453 (13)	0.0437 (14)	0.0332 (14)	0.0104 (11)	0.0143 (11)	0.0185 (12)
C12	0.0600 (16)	0.0440 (15)	0.0440 (17)	0.0136 (12)	0.0238 (13)	0.0194 (13)
C13	0.0719 (19)	0.0639 (19)	0.0479 (19)	0.0236 (15)	0.0332 (15)	0.0259 (15)
C14	0.0498 (15)	0.0613 (18)	0.0529 (19)	0.0113 (13)	0.0191 (14)	0.0337 (15)
C15	0.0564 (16)	0.0446 (16)	0.0527 (19)	0.0063 (12)	0.0109 (14)	0.0239 (14)
C16	0.0556 (15)	0.0453 (15)	0.0392 (16)	0.0126 (12)	0.0174 (13)	0.0166 (13)
C17	0.077 (2)	0.088 (2)	0.079 (3)	0.0165 (18)	0.0374 (19)	0.054 (2)
N1	0.0508 (12)	0.0516 (13)	0.0391 (13)	0.0097 (10)	0.0199 (10)	0.0225 (11)
N2	0.0565 (13)	0.0517 (13)	0.0335 (13)	0.0030 (10)	0.0177 (11)	0.0180 (11)
N3	0.0510 (13)	0.0505 (13)	0.0385 (13)	0.0037 (10)	0.0160 (11)	0.0180 (11)
N4	0.0544 (13)	0.0484 (13)	0.0357 (13)	0.0005 (10)	0.0138 (11)	0.0149 (11)
N5	0.0478 (12)	0.0430 (12)	0.0338 (12)	0.0092 (9)	0.0156 (10)	0.0169 (10)
O1	0.0732 (13)	0.0607 (13)	0.0347 (12)	−0.0031 (10)	0.0198 (10)	0.0131 (10)
S1	0.0562 (4)	0.0576 (5)	0.0451 (5)	0.0080 (3)	0.0177 (3)	0.0243 (4)

Geometric parameters (Å, º)

C1—C2	1.358 (5)	C10—H10B	0.9600
C1—S1	1.703 (3)	C10—H10C	0.9600
C1—H1	0.9300	C11—C12	1.380 (4)
C2—C3	1.410 (5)	C11—C16	1.380 (4)
C2—H2	0.9300	C11—N5	1.435 (3)
C3—C4	1.385 (4)	C12—C13	1.380 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.462 (4)	C13—C14	1.384 (4)
C4—S1	1.719 (3)	C13—H13	0.9300
C5—N1	1.284 (3)	C14—C15	1.388 (4)
C5—C6	1.504 (4)	C14—C17	1.513 (4)
C6—H6A	0.9600	C15—C16	1.384 (4)
C6—H6B	0.9600	C15—H15	0.9300
C6—H6C	0.9600	C16—H16	0.9300
C7—O1	1.217 (3)	C17—H17A	0.9600
C7—N2	1.354 (3)	C17—H17B	0.9600
C7—C8	1.479 (4)	C17—H17C	0.9600
C8—N3	1.358 (3)	N1—N2	1.372 (3)
C8—C9	1.375 (3)	N2—H2A	0.8600
C9—N5	1.358 (3)	N3—N4	1.305 (3)
C9—C10	1.486 (4)	N4—N5	1.364 (3)
C10—H10A	0.9600
C2—C1—S1	112.2 (3)	H10B—C10—H10C	109.5
C2—C1—H1	123.9	C12—C11—C16	121.0 (2)
S1—C1—H1	123.9	C12—C11—N5	118.6 (2)
C1—C2—C3	112.8 (3)	C16—C11—N5	120.4 (2)
C1—C2—H2	123.6	C13—C12—C11	118.8 (3)
C3—C2—H2	123.6	C13—C12—H12	120.6
C4—C3—C2	112.3 (3)	C11—C12—H12	120.6
C4—C3—H3	123.8	C12—C13—C14	121.9 (3)
C2—C3—H3	123.8	C12—C13—H13	119.0
C3—C4—C5	128.1 (3)	C14—C13—H13	119.0
C3—C4—S1	110.7 (2)	C13—C14—C15	117.8 (3)
C5—C4—S1	121.11 (19)	C13—C14—C17	121.3 (3)
N1—C5—C4	115.4 (2)	C15—C14—C17	120.8 (3)
N1—C5—C6	125.0 (3)	C16—C15—C14	121.4 (3)
C4—C5—C6	119.6 (2)	C16—C15—H15	119.3
C5—C6—H6A	109.5	C14—C15—H15	119.3
C5—C6—H6B	109.5	C11—C16—C15	119.0 (3)
H6A—C6—H6B	109.5	C11—C16—H16	120.5
C5—C6—H6C	109.5	C15—C16—H16	120.5
H6A—C6—H6C	109.5	C14—C17—H17A	109.5
H6B—C6—H6C	109.5	C14—C17—H17B	109.5
O1—C7—N2	124.6 (3)	H17A—C17—H17B	109.5
O1—C7—C8	122.6 (2)	C14—C17—H17C	109.5
N2—C7—C8	112.8 (2)	H17A—C17—H17C	109.5
N3—C8—C9	109.3 (2)	H17B—C17—H17C	109.5
N3—C8—C7	122.5 (2)	C5—N1—N2	116.6 (2)
C9—C8—C7	128.1 (2)	C7—N2—N1	121.1 (2)
N5—C9—C8	103.6 (2)	C7—N2—H2A	119.5
N5—C9—C10	124.4 (2)	N1—N2—H2A	119.5
C8—C9—C10	131.9 (3)	N4—N3—C8	109.2 (2)
C9—C10—H10A	109.5	N3—N4—N5	107.0 (2)
C9—C10—H10B	109.5	C9—N5—N4	110.9 (2)
H10A—C10—H10B	109.5	C9—N5—C11	129.9 (2)
C9—C10—H10C	109.5	N4—N5—C11	119.1 (2)
H10A—C10—H10C	109.5	C1—S1—C4	92.00 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1	0.96	2.53	3.124 (4)	120
C16—H16···O1^i	0.93	2.55	3.437 (4)	161

Symmetry code: (i) −x+1, −y+2, −z.