(Z)-Benzyl 2-(5-methyl-2-oxoindolin-3-yl­idene)hydrazinecarbodi­thio­ate

The title compound, C₁₇H₁₅N₃OS₂ was obtained from the condensation reaction of S-benzyl­dithio­carbazate and 5-methyl­isatin. In the solid-state, the mol­ecule adopts a Z configuration with the 5-methyl­isatin and di­thio­carbazate groups located on the same side of the C=N bond, involving an intra­molecular N—H...O hydrogen bond.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.097
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S10      --C10      .        7.6 s.u.

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S11      --C10      .        5.1 s.u.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         38 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        85% Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.9 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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

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Computing details

Data collection: CrysAlis PRO 1.171.42.94a (Rigaku OD, 2023); cell refinement: CrysAlis PRO 1.171.42.94a (Rigaku OD, 2023); data reduction: CrysAlis PRO 1.171.42.94a (Rigaku OD, 2023); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

(Z)-Benzyl 2-(5-methyl-2-oxoindolin-3-ylidene)hydrazinecarbodithioate

Crystal data

C17H15N3OS2	Z = 2
Mr = 341.44	F(000) = 356
Triclinic, P1	Dx = 1.378 Mg m^−3
a = 6.5733 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.0601 (2) Å	Cell parameters from 8603 reflections
c = 15.8280 (4) Å	θ = 2.8–66.0°
α = 95.442 (2)°	µ = 2.99 mm^−1
β = 99.527 (2)°	T = 173 K
γ = 90.360 (2)°	Plate, yellow
V = 823.09 (4) Å^3	0.12 × 0.09 × 0.02 mm

Data collection

Rigaku XtaLAB P100K diffractometer	2876 independent reflections
Radiation source: Rotating Anode, Rigaku MM-007HF	2623 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	Rint = 0.034
Detector resolution: 5.8140 pixels mm^-1	θmax = 66.5°, θmin = 2.8°
shutterless scans	h = −7→7
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023)	k = −9→9
Tmin = 0.748, Tmax = 1.000	l = −18→18
14207 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 0.1676P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2876 reflections	Δρmax = 0.38 e Å^−3
217 parameters	Δρmin = −0.17 e Å^−3
2 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.

Refinement. Carbon-bound H atoms were included in calculated positions (C—H distances are 0.98 Å for methyl H atoms, 0.99 Å for methylene H atoms 0.95 Å for phenyl H atoms) and refined as riding atoms with U_iso(H) = 1.2 U_eq(parent atom, methylene and phenyl H atoms) or U_iso(H) = 1.5 U_eq(parent atom, methyl H atoms). Nitrogen-bound hydrogen atoms were located from the difference Fourier map and refined isotropically subject to a distance restraint.

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

	x	y	z	Uiso*/Ueq
S11	0.21331 (6)	0.33788 (5)	0.21855 (2)	0.03493 (14)
S10	0.58661 (6)	0.23720 (6)	0.13457 (3)	0.04020 (15)
O1	0.86838 (18)	0.08666 (16)	0.40267 (8)	0.0398 (3)
N3	0.5546 (2)	0.22521 (17)	0.29604 (9)	0.0341 (3)
N2	0.4614 (2)	0.26067 (17)	0.36534 (9)	0.0326 (3)
N9	0.7901 (2)	0.11126 (18)	0.54096 (9)	0.0358 (3)
C12	0.1188 (3)	0.5709 (2)	0.10260 (10)	0.0337 (3)
C1	0.7576 (2)	0.1314 (2)	0.45642 (11)	0.0335 (3)
C2	0.5567 (2)	0.22039 (19)	0.43850 (10)	0.0325 (3)
C10	0.4621 (2)	0.26451 (19)	0.21733 (10)	0.0319 (3)
C8	0.6299 (2)	0.1807 (2)	0.58149 (11)	0.0340 (3)
C3	0.4846 (2)	0.24993 (19)	0.52025 (10)	0.0324 (3)
C5	0.2894 (3)	0.3413 (2)	0.63055 (11)	0.0378 (4)
C11	0.1296 (3)	0.3858 (2)	0.10785 (10)	0.0359 (4)
H11A	0.227507	0.338283	0.071281	0.043*
H11B	−0.007988	0.333708	0.085640	0.043*
C4	0.3146 (3)	0.3301 (2)	0.54485 (11)	0.0365 (4)
H4	0.216108	0.376892	0.503346	0.044*
C7	0.6075 (3)	0.1888 (2)	0.66702 (11)	0.0394 (4)
H7	0.705150	0.140761	0.708391	0.047*
C6	0.4357 (3)	0.2702 (2)	0.69000 (11)	0.0415 (4)
H6	0.417242	0.277589	0.748510	0.050*
C17	−0.0561 (3)	0.6540 (2)	0.11867 (12)	0.0452 (4)
H17	−0.169973	0.593731	0.131545	0.054*
C13	0.2833 (3)	0.6589 (3)	0.08239 (12)	0.0478 (5)
H13	0.403301	0.602050	0.070803	0.057*
C9	0.1083 (3)	0.4309 (3)	0.65976 (12)	0.0474 (4)
H9A	0.023698	0.475703	0.610469	0.071*
H9B	0.158867	0.522536	0.703588	0.071*
H9C	0.024801	0.352666	0.684170	0.071*
C16	−0.0654 (5)	0.8257 (3)	0.11601 (14)	0.0685 (7)
H16	−0.184886	0.883158	0.127739	0.082*
C14	0.2728 (5)	0.8293 (3)	0.07910 (14)	0.0690 (8)
H14	0.385349	0.889230	0.064934	0.083*
C15	0.1000 (6)	0.9125 (3)	0.09623 (15)	0.0803 (10)
H15	0.094106	1.029931	0.094482	0.096*
H3	0.680 (3)	0.177 (3)	0.3057 (14)	0.052 (6)*
H9	0.901 (3)	0.053 (3)	0.5684 (14)	0.057 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S11	0.0346 (2)	0.0399 (2)	0.0312 (2)	0.01365 (17)	0.00499 (16)	0.00834 (16)
S10	0.0370 (2)	0.0487 (3)	0.0375 (2)	0.00624 (18)	0.01188 (17)	0.00715 (18)
O1	0.0344 (6)	0.0487 (7)	0.0373 (6)	0.0126 (5)	0.0052 (5)	0.0097 (5)
N3	0.0297 (7)	0.0389 (7)	0.0345 (7)	0.0087 (6)	0.0044 (6)	0.0085 (6)
N2	0.0320 (7)	0.0332 (7)	0.0325 (7)	0.0056 (5)	0.0030 (5)	0.0060 (5)
N9	0.0306 (7)	0.0424 (8)	0.0334 (7)	0.0086 (6)	0.0001 (5)	0.0081 (6)
C12	0.0413 (9)	0.0329 (8)	0.0249 (7)	0.0039 (7)	−0.0017 (6)	0.0050 (6)
C1	0.0294 (8)	0.0337 (8)	0.0365 (8)	0.0042 (6)	0.0015 (6)	0.0063 (6)
C2	0.0300 (8)	0.0310 (8)	0.0360 (8)	0.0046 (6)	0.0021 (6)	0.0067 (6)
C10	0.0320 (8)	0.0278 (7)	0.0353 (8)	0.0019 (6)	0.0031 (6)	0.0046 (6)
C8	0.0306 (8)	0.0349 (8)	0.0351 (8)	0.0018 (6)	0.0005 (6)	0.0054 (6)
C3	0.0313 (8)	0.0317 (8)	0.0332 (8)	0.0019 (6)	0.0010 (6)	0.0055 (6)
C5	0.0335 (8)	0.0406 (9)	0.0386 (9)	−0.0002 (7)	0.0056 (7)	0.0010 (7)
C11	0.0403 (9)	0.0351 (8)	0.0303 (8)	0.0067 (7)	−0.0016 (6)	0.0055 (6)
C4	0.0338 (8)	0.0364 (9)	0.0383 (9)	0.0051 (7)	0.0021 (7)	0.0054 (7)
C7	0.0355 (9)	0.0483 (10)	0.0332 (8)	0.0024 (7)	−0.0010 (7)	0.0089 (7)
C6	0.0396 (9)	0.0511 (10)	0.0333 (9)	−0.0013 (8)	0.0056 (7)	0.0019 (7)
C17	0.0529 (11)	0.0452 (10)	0.0376 (9)	0.0157 (8)	0.0049 (8)	0.0083 (7)
C13	0.0509 (10)	0.0534 (11)	0.0367 (9)	−0.0098 (9)	−0.0009 (8)	0.0076 (8)
C9	0.0419 (10)	0.0576 (11)	0.0428 (10)	0.0067 (8)	0.0102 (8)	−0.0013 (8)
C16	0.105 (2)	0.0485 (12)	0.0467 (12)	0.0390 (13)	−0.0009 (12)	0.0012 (9)
C14	0.104 (2)	0.0527 (13)	0.0441 (12)	−0.0332 (14)	−0.0100 (12)	0.0135 (10)
C15	0.155 (3)	0.0294 (10)	0.0451 (12)	−0.0012 (15)	−0.0179 (15)	0.0056 (9)

Geometric parameters (Å, º)

S11—C10	1.7449 (16)	C5—C6	1.396 (3)
S11—C11	1.8260 (16)	C5—C9	1.510 (3)
S10—C10	1.6544 (16)	C11—H11A	0.9900
O1—C1	1.239 (2)	C11—H11B	0.9900
N3—N2	1.3509 (19)	C4—H4	0.9500
N3—C10	1.360 (2)	C7—H7	0.9500
N3—H3	0.912 (16)	C7—C6	1.392 (3)
N2—C2	1.293 (2)	C6—H6	0.9500
N9—C1	1.345 (2)	C17—H17	0.9500
N9—C8	1.413 (2)	C17—C16	1.390 (3)
N9—H9	0.938 (16)	C13—H13	0.9500
C12—C11	1.503 (2)	C13—C14	1.381 (3)
C12—C17	1.381 (3)	C9—H9A	0.9800
C12—C13	1.387 (2)	C9—H9B	0.9800
C1—C2	1.505 (2)	C9—H9C	0.9800
C2—C3	1.449 (2)	C16—H16	0.9500
C8—C3	1.402 (2)	C16—C15	1.384 (4)
C8—C7	1.381 (2)	C14—H14	0.9500
C3—C4	1.387 (2)	C14—C15	1.375 (4)
C5—C4	1.388 (2)	C15—H15	0.9500
C10—S11—C11	103.16 (8)	C12—C11—H11B	109.4
N2—N3—C10	119.92 (14)	H11A—C11—H11B	108.0
N2—N3—H3	116.6 (14)	C3—C4—C5	119.52 (16)
C10—N3—H3	123.4 (14)	C3—C4—H4	120.2
C2—N2—N3	117.17 (14)	C5—C4—H4	120.2
C1—N9—C8	111.27 (14)	C8—C7—H7	121.4
C1—N9—H9	123.9 (15)	C8—C7—C6	117.16 (16)
C8—N9—H9	124.7 (15)	C6—C7—H7	121.4
C17—C12—C11	119.66 (16)	C5—C6—H6	118.7
C17—C12—C13	119.77 (17)	C7—C6—C5	122.66 (16)
C13—C12—C11	120.57 (16)	C7—C6—H6	118.7
O1—C1—N9	127.80 (15)	C12—C17—H17	120.0
O1—C1—C2	125.75 (15)	C12—C17—C16	120.0 (2)
N9—C1—C2	106.46 (14)	C16—C17—H17	120.0
N2—C2—C1	128.01 (15)	C12—C13—H13	120.0
N2—C2—C3	125.68 (15)	C14—C13—C12	120.0 (2)
C3—C2—C1	106.30 (13)	C14—C13—H13	120.0
S10—C10—S11	128.14 (10)	C5—C9—H9A	109.5
N3—C10—S11	112.22 (12)	C5—C9—H9B	109.5
N3—C10—S10	119.64 (13)	C5—C9—H9C	109.5
C3—C8—N9	109.25 (14)	H9A—C9—H9B	109.5
C7—C8—N9	129.31 (15)	H9A—C9—H9C	109.5
C7—C8—C3	121.43 (16)	H9B—C9—H9C	109.5
C8—C3—C2	106.70 (14)	C17—C16—H16	120.1
C4—C3—C2	133.05 (15)	C15—C16—C17	119.8 (2)
C4—C3—C8	120.24 (16)	C15—C16—H16	120.1
C4—C5—C6	118.99 (16)	C13—C14—H14	119.9
C4—C5—C9	120.83 (16)	C15—C14—C13	120.3 (2)
C6—C5—C9	120.18 (16)	C15—C14—H14	119.9
S11—C11—H11A	109.4	C16—C15—H15	119.9
S11—C11—H11B	109.4	C14—C15—C16	120.1 (2)
C12—C11—S11	111.12 (11)	C14—C15—H15	119.9
C12—C11—H11A	109.4
O1—C1—C2—N2	2.5 (3)	C8—N9—C1—O1	179.33 (16)
O1—C1—C2—C3	−178.95 (16)	C8—N9—C1—C2	−0.72 (18)
N3—N2—C2—C1	−2.7 (2)	C8—C3—C4—C5	0.0 (2)
N3—N2—C2—C3	178.99 (14)	C8—C7—C6—C5	0.2 (3)
N2—N3—C10—S11	−6.67 (19)	C3—C8—C7—C6	−0.7 (3)
N2—N3—C10—S10	174.23 (11)	C11—S11—C10—S10	−2.51 (13)
N2—C2—C3—C8	177.57 (15)	C11—S11—C10—N3	178.48 (11)
N2—C2—C3—C4	−3.7 (3)	C11—C12—C17—C16	178.43 (17)
N9—C1—C2—N2	−177.48 (15)	C11—C12—C13—C14	−178.98 (16)
N9—C1—C2—C3	1.09 (17)	C4—C5—C6—C7	0.4 (3)
N9—C8—C3—C2	0.65 (18)	C7—C8—C3—C2	179.54 (15)
N9—C8—C3—C4	−178.28 (14)	C7—C8—C3—C4	0.6 (2)
N9—C8—C7—C6	177.93 (16)	C6—C5—C4—C3	−0.5 (3)
C12—C17—C16—C15	0.8 (3)	C17—C12—C11—S11	−84.17 (17)
C12—C13—C14—C15	0.3 (3)	C17—C12—C13—C14	0.5 (3)
C1—N9—C8—C3	0.07 (19)	C17—C16—C15—C14	0.1 (3)
C1—N9—C8—C7	−178.72 (17)	C13—C12—C11—S11	95.35 (16)
C1—C2—C3—C8	−1.05 (17)	C13—C12—C17—C16	−1.1 (3)
C1—C2—C3—C4	177.68 (17)	C13—C14—C15—C16	−0.7 (3)
C2—C3—C4—C5	−178.56 (16)	C9—C5—C4—C3	178.71 (16)
C10—S11—C11—C12	−109.04 (13)	C9—C5—C6—C7	−178.83 (16)
C10—N3—N2—C2	179.99 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.91 (2)	2.00 (2)	2.7539 (17)	139 (2)
N9—H9···O1^i	0.94 (2)	1.91 (2)	2.8341 (18)	166 (2)

Symmetry code: (i) −x+2, −y, −z+1.