Crystal structure of (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methyl-idene]hydrazine-carbo-thio-amide.

In the title compound, C12H11N3O2S, the dihedral angle between the 4H-chromen-4-one ring system and the -CH=N-NH-CS-NH- unit is 6.22 (1)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(14) loops. The dimers are reinforced by a pair of C-H⋯O inter-actions, which generate R 2 (2)(10) loops.

Related literature

For the biological properties of related compounds, see: Khan et al. (2009 ▶); Tu et al. (2013 ▶); Kelly et al. (1996 ▶). For a related structure, see: Ishikawa & Watanabe (2014 ▶).

Experimental

Crystal data

C12H11N3O2S

M = 261.30

Monoclinic,

a = 6.3702 (7) Å

b = 20.647 (2) Å

c = 9.2717 (10) Å

β = 98.365 (3)°

V = 1206.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.924, T max = 0.948

17429 measured reflections

3560 independent reflections

2257 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 1.06

3560 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814021667/hb7287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021667/hb7287Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021667/hb7287Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814021667/hb7287fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814021667/hb7287fig2.tif

The packing of the title compound with hydrogen bonds represented by dashed lines. Hydrogen atoms not involved in these bonds are omitted for clarity.

CCDC reference: 1027156

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H11N3O2S	Z = 4
Mr = 261.30	F(000) = 544
Monoclinic, P21/n	Dx = 1.439 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.3702 (7) Å	µ = 0.27 mm−1
b = 20.647 (2) Å	T = 293 K
c = 9.2717 (10) Å	Block, colourless
β = 98.365 (3)°	0.30 × 0.25 × 0.20 mm
V = 1206.5 (2) Å3

Bruker SMART APEXII CCD diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	2257 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 30.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.924, Tmax = 0.948	k = −28→28
17429 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.056P)2 + 0.3687P] where P = (Fo2 + 2Fc2)/3
3560 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
C1	1.1216 (3)	−0.01086 (8)	−0.30947 (18)	0.0402 (4)
C2	1.2628 (3)	−0.03414 (11)	−0.3973 (2)	0.0536 (5)
H2	1.3795	−0.0097	−0.4138	0.064*
C3	1.2268 (4)	−0.09395 (12)	−0.4591 (2)	0.0615 (6)
H3	1.3198	−0.1102	−0.5187	0.074*
C4	1.0550 (4)	−0.13046 (11)	−0.4344 (2)	0.0590 (6)
H4	1.0321	−0.1708	−0.4784	0.071*
C5	0.9167 (3)	−0.10774 (9)	−0.3453 (2)	0.0485 (5)
H5	0.8020	−0.1329	−0.3279	0.058*
C6	0.9493 (3)	−0.04658 (8)	−0.28081 (17)	0.0359 (4)
C7	0.8095 (3)	−0.02066 (8)	−0.18335 (17)	0.0353 (4)
C8	0.8552 (3)	0.04523 (7)	−0.13502 (17)	0.0336 (3)
C9	1.0264 (3)	0.07560 (8)	−0.1711 (2)	0.0429 (4)
H9	1.0518	0.1177	−0.1376	0.051*
C10	0.7153 (3)	0.07618 (8)	−0.04415 (18)	0.0373 (4)
H10	0.5918	0.0552	−0.0274	0.045*
C11	0.6662 (3)	0.21399 (7)	0.16614 (18)	0.0367 (4)
C12	0.9249 (4)	0.30201 (10)	0.2112 (3)	0.0619 (6)
H12A	0.8427	0.3380	0.1689	0.093*
H12B	1.0703	0.3075	0.1976	0.093*
H12C	0.9158	0.2998	0.3136	0.093*
N1	0.7607 (2)	0.13156 (6)	0.01244 (15)	0.0367 (3)
N2	0.6206 (2)	0.15691 (6)	0.09629 (16)	0.0400 (3)
H2A	0.5048	0.1368	0.1046	0.048*
N3	0.8432 (3)	0.24283 (7)	0.14142 (18)	0.0456 (4)
H3A	0.9141	0.2252	0.0797	0.055*
O1	1.1633 (2)	0.04988 (6)	−0.25169 (15)	0.0482 (3)
O2	0.6644 (2)	−0.05230 (6)	−0.14399 (16)	0.0550 (4)
S1	0.49924 (9)	0.24309 (2)	0.27366 (6)	0.05253 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0460 (10)	0.0399 (9)	0.0355 (9)	0.0073 (7)	0.0089 (7)	0.0057 (7)
C2	0.0545 (12)	0.0624 (12)	0.0470 (11)	0.0127 (10)	0.0180 (9)	0.0078 (9)
C3	0.0724 (15)	0.0678 (14)	0.0469 (12)	0.0299 (12)	0.0167 (10)	0.0005 (10)
C4	0.0805 (16)	0.0484 (11)	0.0468 (11)	0.0189 (11)	0.0050 (11)	−0.0096 (9)
C5	0.0583 (12)	0.0403 (9)	0.0451 (10)	0.0052 (8)	0.0011 (9)	−0.0057 (8)
C6	0.0422 (9)	0.0336 (8)	0.0307 (8)	0.0050 (7)	0.0018 (7)	0.0015 (6)
C7	0.0365 (9)	0.0348 (8)	0.0339 (8)	−0.0016 (6)	0.0024 (7)	−0.0008 (6)
C8	0.0377 (9)	0.0302 (7)	0.0328 (8)	−0.0005 (6)	0.0052 (7)	0.0005 (6)
C9	0.0517 (11)	0.0329 (8)	0.0463 (10)	−0.0033 (7)	0.0147 (8)	0.0002 (7)
C10	0.0397 (9)	0.0353 (8)	0.0375 (9)	−0.0028 (7)	0.0080 (7)	−0.0028 (7)
C11	0.0430 (10)	0.0274 (7)	0.0401 (9)	0.0026 (6)	0.0072 (7)	0.0012 (6)
C12	0.0564 (13)	0.0406 (10)	0.0913 (17)	−0.0104 (9)	0.0190 (12)	−0.0151 (10)
N1	0.0445 (8)	0.0310 (7)	0.0357 (7)	0.0011 (6)	0.0097 (6)	−0.0006 (5)
N2	0.0427 (8)	0.0328 (7)	0.0469 (8)	−0.0036 (6)	0.0150 (7)	−0.0058 (6)
N3	0.0500 (9)	0.0330 (7)	0.0578 (10)	−0.0036 (6)	0.0213 (8)	−0.0072 (6)
O1	0.0510 (8)	0.0410 (7)	0.0572 (8)	−0.0043 (5)	0.0233 (6)	0.0007 (6)
O2	0.0539 (8)	0.0445 (7)	0.0712 (10)	−0.0181 (6)	0.0241 (7)	−0.0158 (6)
S1	0.0572 (3)	0.0399 (3)	0.0659 (4)	0.0015 (2)	0.0269 (3)	−0.0093 (2)

C1—O1	1.374 (2)	C8—C10	1.460 (2)
C1—C6	1.380 (2)	C9—O1	1.338 (2)
C1—C2	1.384 (3)	C9—H9	0.9300
C2—C3	1.367 (3)	C10—N1	1.274 (2)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.375 (3)	C11—N3	1.324 (2)
C3—H3	0.9300	C11—N2	1.356 (2)
C4—C5	1.375 (3)	C11—S1	1.6715 (17)
C4—H4	0.9300	C12—N3	1.444 (2)
C5—C6	1.400 (2)	C12—H12A	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C6—C7	1.459 (2)	C12—H12C	0.9600
C7—O2	1.230 (2)	N1—N2	1.3695 (18)
C7—C8	1.449 (2)	N2—H2A	0.8600
C8—C9	1.342 (2)	N3—H3A	0.8600
O1—C1—C6	121.78 (15)	O1—C9—C8	124.97 (16)
O1—C1—C2	116.17 (17)	O1—C9—H9	117.5
C6—C1—C2	122.05 (17)	C8—C9—H9	117.5
C3—C2—C1	118.5 (2)	N1—C10—C8	120.64 (15)
C3—C2—H2	120.8	N1—C10—H10	119.7
C1—C2—H2	120.8	C8—C10—H10	119.7
C2—C3—C4	121.0 (2)	N3—C11—N2	115.89 (15)
C2—C3—H3	119.5	N3—C11—S1	124.97 (13)
C4—C3—H3	119.5	N2—C11—S1	119.14 (13)
C5—C4—C3	120.5 (2)	N3—C12—H12A	109.5
C5—C4—H4	119.7	N3—C12—H12B	109.5
C3—C4—H4	119.7	H12A—C12—H12B	109.5
C4—C5—C6	119.8 (2)	N3—C12—H12C	109.5
C4—C5—H5	120.1	H12A—C12—H12C	109.5
C6—C5—H5	120.1	H12B—C12—H12C	109.5
C1—C6—C5	118.20 (16)	C10—N1—N2	116.71 (14)
C1—C6—C7	119.82 (15)	C11—N2—N1	119.45 (14)
C5—C6—C7	121.97 (16)	C11—N2—H2A	120.3
O2—C7—C8	122.21 (15)	N1—N2—H2A	120.3
O2—C7—C6	122.79 (15)	C11—N3—C12	124.28 (16)
C8—C7—C6	115.00 (14)	C11—N3—H3A	117.9
C9—C8—C7	119.72 (15)	C12—N3—H3A	117.9
C9—C8—C10	121.73 (15)	C9—O1—C1	118.35 (14)
C7—C8—C10	118.52 (14)
O1—C1—C2—C3	−179.09 (17)	C6—C7—C8—C9	−5.2 (2)
C6—C1—C2—C3	1.2 (3)	O2—C7—C8—C10	−4.0 (2)
C1—C2—C3—C4	−0.3 (3)	C6—C7—C8—C10	176.46 (14)
C2—C3—C4—C5	−0.8 (3)	C7—C8—C9—O1	0.6 (3)
C3—C4—C5—C6	0.9 (3)	C10—C8—C9—O1	178.80 (16)
O1—C1—C6—C5	179.29 (15)	C9—C8—C10—N1	−5.1 (3)
C2—C1—C6—C5	−1.0 (3)	C7—C8—C10—N1	173.16 (15)
O1—C1—C6—C7	−1.8 (2)	C8—C10—N1—N2	−179.90 (14)
C2—C1—C6—C7	177.85 (16)	N3—C11—N2—N1	3.0 (2)
C4—C5—C6—C1	−0.1 (3)	S1—C11—N2—N1	−177.53 (12)
C4—C5—C6—C7	−178.91 (17)	C10—N1—N2—C11	176.29 (15)
C1—C6—C7—O2	−173.71 (17)	N2—C11—N3—C12	−176.58 (18)
C5—C6—C7—O2	5.1 (3)	S1—C11—N3—C12	4.0 (3)
C1—C6—C7—C8	5.8 (2)	C8—C9—O1—C1	3.8 (3)
C5—C6—C7—C8	−175.36 (16)	C6—C1—O1—C9	−3.1 (2)
O2—C7—C8—C9	174.28 (17)	C2—C1—O1—C9	177.22 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.11	2.897 (2)	152
C10—H10···O2i	0.93	2.44	3.219 (2)	141

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2AO2i	0.86	2.11	2.897(2)	152
C10H10O2i	0.93	2.44	3.219(2)	141

Symmetry code: (i) .