Triethyl-ammonium N'-(benzyl-sulfanylthio-carbonyl)-2-hydroxy-benzohydrazidate.

In the title compound, C(6)H(16)N(+)·C(15)H(13)N(2)O(2)S(2) (-), the thione S atom is in a cis configuration with respect to the phenyl and benzene rings, while it adopts a trans configuration with respect to the carbonyl group. The dihedral angle between the benzene and phenyl rings is 78.81 (2)°. The mol-ecular conformation is stabilized by intra-molecular O-H⋯O and N-H⋯S hydrogen bonds, while inter-molecular N-H⋯O, N-H⋯N and weak C-H⋯O inter-actions help to stabilize the crystal structure.

Related literature

For related literature, see: Scovill et al. (1982 ▶, 1984 ▶); West et al. (1989 ▶); Gou et al. (1990 ▶); Abu-Raquabah et al. (1992 ▶); Marchi et al. (1990 ▶); Ali & Livingston, (1974 ▶); Wu et al. (2000); Boga et al. (1990 ▶).

Experimental

Crystal data

C6H16N+·C15n class="Species">H13N2O2S2 −

M = 419.59

Orthorhombic,

a = 10.7109 (4) Å

b = 18.6807 (6) Å

c = 22.1814 (7) Å

V = 4438.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 173 (2) K

0.08 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

26195 measured reflections

3928 independent reflections

2542 reflections with I > 2σ(I)

R int = 0.138

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.118

S = 1.05

3928 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.23 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067037/lh2550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067037/lh2550Isup2.hkl

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

C6H16N+·C15H13N2O2S2–	Dx = 1.256 Mg m−3
Mr = 419.59	Melting point: 418 K
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 16320 reflections
a = 10.7109 (4) Å	θ = 1.0–26.0º
b = 18.6807 (6) Å	µ = 0.26 mm−1
c = 22.1814 (7) Å	T = 173 (2) K
V = 4438.2 (3) Å3	Chip, yellow
Z = 8	0.08 × 0.08 × 0.05 mm
F000 = 1792

Nonius KappaCCD diffractometer	2542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.138
Monochromator: horizonally mounted graphite crystal	θmax = 25.0º
T = 173(2) K	θmin = 2.4º
φ scans and ω scans with κ offsets	h = −12→12
Absorption correction: none	k = −22→20
26195 measured reflections	l = −26→26
3928 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.033P)2 + 3.4211P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.056	(Δ/σ)max < 0.001
wR(F2) = 0.118	Δρmax = 0.34 e Å−3
S = 1.05	Δρmin = −0.23 e Å−3
3928 reflections	Extinction correction: none
257 parameters

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	0.15592 (9)	0.33158 (5)	−0.05488 (4)	0.0436 (2)
S2	0.34667 (8)	0.44725 (4)	−0.01971 (4)	0.0380 (2)
O1	0.5287 (2)	0.23266 (12)	0.22154 (10)	0.0454 (6)
H1	0.4638	0.2259	0.2010	0.068*
O2	0.3691 (2)	0.25376 (12)	0.13887 (10)	0.0427 (6)
N1	0.3824 (2)	0.35026 (14)	0.07825 (12)	0.0351 (7)
H1A	0.4152	0.3928	0.0719	0.042*
N2	0.2880 (2)	0.32553 (13)	0.04023 (11)	0.0335 (6)
C1	0.5386 (3)	0.33468 (16)	0.15530 (13)	0.0302 (7)
C2	0.5870 (3)	0.29257 (17)	0.20199 (14)	0.0348 (8)
C3	0.6992 (3)	0.31114 (19)	0.22951 (15)	0.0434 (9)
H3	0.7313	0.2825	0.2613	0.052*
C4	0.7638 (3)	0.3707 (2)	0.21095 (16)	0.0462 (9)
H4	0.8408	0.3826	0.2297	0.055*
C5	0.7178 (3)	0.41331 (19)	0.16532 (15)	0.0431 (9)
H5	0.7627	0.4546	0.1528	0.052*
C6	0.6067 (3)	0.39574 (17)	0.13812 (15)	0.0376 (8)
H6	0.5751	0.4256	0.1070	0.045*
C7	0.4235 (3)	0.31073 (17)	0.12389 (14)	0.0332 (8)
C8	0.2719 (3)	0.36876 (16)	−0.00578 (14)	0.0320 (7)
C9	0.1697 (3)	0.38403 (17)	−0.12303 (14)	0.0395 (8)
H9A	0.2505	0.4097	−0.1220	0.047*
H9B	0.1719	0.3509	−0.1579	0.047*
C10	0.0678 (3)	0.43768 (17)	−0.13339 (14)	0.0355 (8)
C11	0.0125 (4)	0.4435 (2)	−0.18983 (16)	0.0501 (10)
H11	0.0358	0.4115	−0.2212	0.060*
C12	−0.0765 (4)	0.4959 (2)	−0.20057 (19)	0.0637 (12)
H12	−0.1135	0.4995	−0.2394	0.076*
C13	−0.1118 (4)	0.5423 (2)	−0.1562 (2)	0.0597 (11)
H13	−0.1723	0.5782	−0.1641	0.072*
C14	−0.0587 (4)	0.53656 (19)	−0.09972 (17)	0.0498 (10)
H14	−0.0833	0.5684	−0.0685	0.060*
C15	0.0300 (3)	0.48471 (17)	−0.08859 (15)	0.0394 (8)
H15	0.0659	0.4812	−0.0495	0.047*
N3	0.1590 (3)	0.18429 (14)	0.07791 (13)	0.0420 (7)
H3A	0.2145	0.2224	0.0807	0.050*
C16	0.1821 (3)	0.14954 (19)	0.01787 (16)	0.0476 (9)
H16A	0.1311	0.1055	0.0149	0.057*
H16B	0.1549	0.1825	−0.0146	0.057*
C17	0.3143 (4)	0.1311 (2)	0.0086 (2)	0.0683 (12)
H17A	0.3663	0.1730	0.0173	0.102*
H17B	0.3271	0.1163	−0.0333	0.102*
H17C	0.3374	0.0919	0.0357	0.102*
C18	0.1836 (3)	0.13709 (19)	0.13117 (17)	0.0498 (10)
H18A	0.1716	0.1655	0.1684	0.060*
H18B	0.2721	0.1218	0.1300	0.060*
C19	0.1015 (4)	0.0707 (2)	0.13475 (18)	0.0589 (11)
H19A	0.0137	0.0851	0.1377	0.088*
H19B	0.1243	0.0426	0.1704	0.088*
H19C	0.1135	0.0416	0.0985	0.088*
C20	0.0303 (4)	0.2161 (2)	0.07594 (17)	0.0527 (10)
H20A	0.0230	0.2461	0.0393	0.063*
H20B	−0.0313	0.1768	0.0725	0.063*
C21	−0.0019 (4)	0.2601 (2)	0.1287 (2)	0.0746 (13)
H21A	−0.0068	0.2295	0.1645	0.112*
H21B	−0.0827	0.2833	0.1220	0.112*
H21C	0.0625	0.2967	0.1347	0.112*

	U11	U22	U33	U12	U13	U23
S1	0.0456 (5)	0.0354 (5)	0.0496 (5)	−0.0055 (4)	−0.0148 (5)	0.0072 (4)
S2	0.0395 (5)	0.0281 (4)	0.0464 (5)	−0.0009 (4)	−0.0008 (4)	0.0027 (4)
O1	0.0535 (16)	0.0388 (14)	0.0439 (14)	−0.0102 (12)	−0.0090 (12)	0.0085 (11)
O2	0.0475 (15)	0.0396 (13)	0.0410 (13)	−0.0169 (12)	−0.0066 (11)	0.0058 (11)
N1	0.0346 (16)	0.0280 (14)	0.0427 (16)	−0.0063 (12)	−0.0066 (13)	0.0005 (12)
N2	0.0323 (16)	0.0312 (15)	0.0371 (15)	−0.0019 (12)	−0.0062 (12)	−0.0018 (12)
C1	0.0301 (18)	0.0315 (17)	0.0289 (17)	−0.0010 (15)	0.0045 (14)	−0.0056 (14)
C2	0.038 (2)	0.0342 (18)	0.0325 (18)	−0.0005 (15)	0.0032 (15)	−0.0045 (15)
C3	0.041 (2)	0.048 (2)	0.041 (2)	0.0036 (17)	−0.0057 (17)	−0.0026 (17)
C4	0.032 (2)	0.057 (2)	0.050 (2)	−0.0019 (18)	−0.0008 (18)	−0.0114 (19)
C5	0.037 (2)	0.045 (2)	0.047 (2)	−0.0115 (17)	0.0063 (17)	−0.0070 (17)
C6	0.042 (2)	0.038 (2)	0.0331 (19)	−0.0028 (16)	0.0044 (16)	−0.0010 (15)
C7	0.035 (2)	0.0324 (18)	0.0322 (18)	0.0019 (15)	−0.0003 (15)	−0.0051 (15)
C8	0.0289 (18)	0.0287 (17)	0.0384 (18)	0.0060 (14)	0.0033 (15)	−0.0024 (15)
C9	0.045 (2)	0.0400 (19)	0.0338 (18)	0.0037 (17)	−0.0032 (16)	−0.0013 (15)
C10	0.0373 (19)	0.0338 (18)	0.0354 (19)	−0.0067 (15)	−0.0019 (16)	0.0044 (15)
C11	0.062 (3)	0.046 (2)	0.043 (2)	0.001 (2)	−0.0073 (19)	0.0019 (17)
C12	0.077 (3)	0.056 (3)	0.058 (3)	0.011 (2)	−0.025 (2)	0.017 (2)
C13	0.059 (3)	0.043 (2)	0.078 (3)	0.010 (2)	−0.002 (2)	0.014 (2)
C14	0.054 (3)	0.041 (2)	0.054 (2)	0.0064 (19)	0.009 (2)	0.0055 (18)
C15	0.041 (2)	0.040 (2)	0.0371 (19)	−0.0008 (17)	0.0039 (16)	0.0043 (16)
N3	0.0357 (16)	0.0339 (15)	0.0564 (18)	−0.0110 (13)	0.0012 (15)	−0.0074 (14)
C16	0.051 (2)	0.040 (2)	0.052 (2)	−0.0060 (18)	−0.0023 (19)	−0.0038 (18)
C17	0.053 (3)	0.066 (3)	0.086 (3)	−0.002 (2)	0.005 (2)	−0.018 (2)
C18	0.046 (2)	0.051 (2)	0.053 (2)	−0.0111 (18)	−0.0063 (19)	−0.0081 (18)
C19	0.062 (3)	0.057 (3)	0.058 (3)	−0.016 (2)	−0.007 (2)	0.006 (2)
C20	0.046 (2)	0.053 (2)	0.059 (2)	−0.0035 (19)	−0.001 (2)	−0.0003 (19)
C21	0.076 (3)	0.068 (3)	0.080 (3)	0.013 (2)	0.008 (3)	−0.021 (2)

S1—C8	1.793 (3)	C12—H12	0.9500
S1—C9	1.807 (3)	C13—C14	1.379 (5)
S2—C8	1.699 (3)	C13—H13	0.9500
O1—C2	1.353 (4)	C14—C15	1.379 (5)
O1—H1	0.8400	C14—H14	0.9500
O2—C7	1.258 (4)	C15—H15	0.9500
N1—C7	1.328 (4)	N3—C18	1.498 (4)
N1—N2	1.395 (3)	N3—C20	1.502 (4)
N1—H1A	0.8800	N3—C16	1.502 (4)
N2—C8	1.313 (4)	N3—H3A	0.9300
C1—C2	1.400 (4)	C16—C17	1.471 (5)
C1—C6	1.407 (4)	C16—H16A	0.9900
C1—C7	1.485 (4)	C16—H16B	0.9900
C2—C3	1.392 (5)	C17—H17A	0.9800
C3—C4	1.374 (5)	C17—H17B	0.9800
C3—H3	0.9500	C17—H17C	0.9800
C4—C5	1.379 (5)	C18—C19	1.523 (5)
C4—H4	0.9500	C18—H18A	0.9900
C5—C6	1.374 (4)	C18—H18B	0.9900
C5—H5	0.9500	C19—H19A	0.9800
C6—H6	0.9500	C19—H19B	0.9800
C9—C10	1.499 (4)	C19—H19C	0.9800
C9—H9A	0.9900	C20—C21	1.470 (5)
C9—H9B	0.9900	C20—H20A	0.9900
C10—C15	1.387 (4)	C20—H20B	0.9900
C10—C11	1.389 (5)	C21—H21A	0.9800
C11—C12	1.387 (5)	C21—H21B	0.9800
C11—H11	0.9500	C21—H21C	0.9800
C12—C13	1.365 (6)
C8—S1—C9	103.99 (15)	C13—C14—C15	120.1 (4)
C2—O1—H1	109.5	C13—C14—H14	120.0
C7—N1—N2	121.1 (3)	C15—C14—H14	120.0
C7—N1—H1A	119.4	C14—C15—C10	121.2 (3)
N2—N1—H1A	119.4	C14—C15—H15	119.4
C8—N2—N1	111.2 (3)	C10—C15—H15	119.4
C2—C1—C6	117.7 (3)	C18—N3—C20	114.7 (3)
C2—C1—C7	119.0 (3)	C18—N3—C16	114.6 (3)
C6—C1—C7	123.2 (3)	C20—N3—C16	107.3 (3)
O1—C2—C3	117.7 (3)	C18—N3—H3A	106.6
O1—C2—C1	122.1 (3)	C20—N3—H3A	106.6
C3—C2—C1	120.3 (3)	C16—N3—H3A	106.6
C4—C3—C2	120.4 (3)	C17—C16—N3	112.5 (3)
C4—C3—H3	119.8	C17—C16—H16A	109.1
C2—C3—H3	119.8	N3—C16—H16A	109.1
C3—C4—C5	120.5 (3)	C17—C16—H16B	109.1
C3—C4—H4	119.8	N3—C16—H16B	109.1
C5—C4—H4	119.8	H16A—C16—H16B	107.8
C6—C5—C4	119.6 (3)	C16—C17—H17A	109.5
C6—C5—H5	120.2	C16—C17—H17B	109.5
C4—C5—H5	120.2	H17A—C17—H17B	109.5
C5—C6—C1	121.6 (3)	C16—C17—H17C	109.5
C5—C6—H6	119.2	H17A—C17—H17C	109.5
C1—C6—H6	119.2	H17B—C17—H17C	109.5
O2—C7—N1	121.2 (3)	N3—C18—C19	114.8 (3)
O2—C7—C1	121.0 (3)	N3—C18—H18A	108.6
N1—C7—C1	117.8 (3)	C19—C18—H18A	108.6
N2—C8—S2	127.6 (2)	N3—C18—H18B	108.6
N2—C8—S1	109.0 (2)	C19—C18—H18B	108.6
S2—C8—S1	123.40 (18)	H18A—C18—H18B	107.6
C10—C9—S1	115.5 (2)	C18—C19—H19A	109.5
C10—C9—H9A	108.4	C18—C19—H19B	109.5
S1—C9—H9A	108.4	H19A—C19—H19B	109.5
C10—C9—H9B	108.4	C18—C19—H19C	109.5
S1—C9—H9B	108.4	H19A—C19—H19C	109.5
H9A—C9—H9B	107.5	H19B—C19—H19C	109.5
C15—C10—C11	118.2 (3)	C21—C20—N3	114.4 (3)
C15—C10—C9	121.7 (3)	C21—C20—H20A	108.7
C11—C10—C9	120.0 (3)	N3—C20—H20A	108.7
C12—C11—C10	120.2 (4)	C21—C20—H20B	108.7
C12—C11—H11	119.9	N3—C20—H20B	108.7
C10—C11—H11	119.9	H20A—C20—H20B	107.6
C13—C12—C11	121.0 (4)	C20—C21—H21A	109.5
C13—C12—H12	119.5	C20—C21—H21B	109.5
C11—C12—H12	119.5	H21A—C21—H21B	109.5
C12—C13—C14	119.4 (4)	C20—C21—H21C	109.5
C12—C13—H13	120.3	H21A—C21—H21C	109.5
C14—C13—H13	120.3	H21B—C21—H21C	109.5
C7—N1—N2—C8	−172.4 (3)	C9—S1—C8—N2	−167.1 (2)
C6—C1—C2—O1	−179.7 (3)	C9—S1—C8—S2	12.3 (2)
C7—C1—C2—O1	−3.5 (4)	C8—S1—C9—C10	−105.5 (3)
C6—C1—C2—C3	−0.5 (4)	S1—C9—C10—C15	48.7 (4)
C7—C1—C2—C3	175.7 (3)	S1—C9—C10—C11	−134.3 (3)
O1—C2—C3—C4	178.9 (3)	C15—C10—C11—C12	0.9 (5)
C1—C2—C3—C4	−0.3 (5)	C9—C10—C11—C12	−176.2 (3)
C2—C3—C4—C5	0.7 (5)	C10—C11—C12—C13	−0.2 (6)
C3—C4—C5—C6	−0.3 (5)	C11—C12—C13—C14	−0.6 (6)
C4—C5—C6—C1	−0.6 (5)	C12—C13—C14—C15	0.6 (6)
C2—C1—C6—C5	0.9 (5)	C13—C14—C15—C10	0.1 (5)
C7—C1—C6—C5	−175.1 (3)	C11—C10—C15—C14	−0.9 (5)
N2—N1—C7—O2	−8.7 (5)	C9—C10—C15—C14	176.2 (3)
N2—N1—C7—C1	169.2 (3)	C18—N3—C16—C17	−64.9 (4)
C2—C1—C7—O2	0.4 (4)	C20—N3—C16—C17	166.6 (3)
C6—C1—C7—O2	176.4 (3)	C20—N3—C18—C19	62.5 (4)
C2—C1—C7—N1	−177.5 (3)	C16—N3—C18—C19	−62.2 (4)
C6—C1—C7—N1	−1.5 (4)	C18—N3—C20—C21	58.6 (4)
N1—N2—C8—S2	−2.5 (4)	C16—N3—C20—C21	−172.9 (3)
N1—N2—C8—S1	176.84 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.79	2.538 (3)	147
N1—H1A···S2	0.88	2.39	2.855 (3)	114
N3—H3A···O2	0.93	2.18	2.929 (3)	137
N3—H3A···N2	0.93	2.27	3.094 (4)	148
C9—H9A···S2	0.99	2.59	3.200 (3)	120
C21—H21A···O1i	0.98	2.56	3.377 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	1.79	2.538 (3)	147
N1—H1A⋯S2	0.88	2.39	2.855 (3)	114
N3—H3A⋯O2	0.93	2.18	2.929 (3)	137
N3—H3A⋯N2	0.93	2.27	3.094 (4)	148
C9—H9A⋯S2	0.99	2.59	3.200 (3)	120
C21—H21A⋯O1i	0.98	2.56	3.377 (5)	141

Symmetry code: (i) .