1-(Furan-2-ylmethyl­ene)-4-phenyl­thio­semicarbazide

In the mol­ecule of the title compound, C₁₂H₁₁N₃OS, the dihedral angle between the planar rings is 59.4 (2)°. The structure is stabilized by intra­molecular N—H...N and inter­molecular N—H...S hydrogen bonds. Inter­molecular N—H...S hydrogen bonds link the independent mol­ecules into dimers.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.180
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    -   C11     ..      10.36 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C9      ..       6.89 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(2-Furylmethylene)-4-phenylthiosemicarbazide

Crystal data

C12H11N3OS	Z = 2
Mr = 245.31	F(000) = 256
Triclinic, P1	Dx = 1.332 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8810 (12) Å	Cell parameters from 25 reflections
b = 9.878 (2) Å	θ = 4–14°
c = 11.186 (2) Å	µ = 0.25 mm^−1
α = 71.45 (3)°	T = 296 K
β = 83.18 (3)°	Block, brown
γ = 88.95 (3)°	0.35 × 0.25 × 0.25 mm
V = 611.6 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.010
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 1.9°
Graphite monochromator	h = 0→7
ω scans	k = −11→12
2889 measured reflections	l = −13→14
2675 independent reflections	3 standard reflections every 100 reflections
1882 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.180	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1127P)^2 + 0.1125P] where P = (Fo^2 + 2Fc^2)/3
2675 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	−0.00860 (11)	0.88112 (8)	0.36216 (6)	0.0568 (3)
O1	0.9002 (4)	1.3198 (3)	0.2645 (2)	0.0859 (7)
N1	0.4182 (3)	0.9470 (2)	0.2383 (2)	0.0517 (5)
H1A	0.5460	0.9911	0.2321	0.062*
N2	0.2959 (4)	1.0658 (2)	0.3766 (2)	0.0507 (5)
H2A	0.2008	1.0786	0.4365	0.061*
N3	0.4977 (3)	1.1451 (2)	0.33697 (19)	0.0473 (5)
C1	0.5891 (5)	0.7683 (3)	0.1526 (3)	0.0586 (7)
H1B	0.7064	0.7605	0.2032	0.070*
C2	0.5921 (5)	0.6884 (3)	0.0697 (3)	0.0658 (8)
H2B	0.7117	0.6267	0.0652	0.079*
C3	0.4183 (5)	0.7005 (3)	−0.0058 (3)	0.0600 (7)
H3B	0.4215	0.6472	−0.0611	0.072*
C4	0.2400 (5)	0.7916 (3)	0.0008 (3)	0.0613 (7)
H4A	0.1226	0.7990	−0.0497	0.074*
C5	0.2351 (4)	0.8722 (3)	0.0826 (2)	0.0523 (6)
H5A	0.1158	0.9344	0.0864	0.063*
C6	0.4102 (4)	0.8591 (2)	0.1588 (2)	0.0450 (5)
C7	0.2480 (4)	0.9684 (2)	0.3215 (2)	0.0432 (5)
C8	0.5265 (4)	1.2403 (3)	0.3894 (2)	0.0506 (6)
H8A	0.4165	1.2503	0.4528	0.061*
C9	0.7263 (5)	1.3318 (3)	0.3514 (2)	0.0514 (6)
C10	0.7627 (5)	1.4413 (3)	0.3950 (3)	0.0606 (7)
H10A	0.6682	1.4706	0.4545	0.073*
C11	0.9788 (8)	1.5019 (4)	0.3294 (5)	0.1004 (15)
H11A	1.0510	1.5807	0.3379	0.120*
C12	1.0581 (6)	1.4289 (5)	0.2557 (5)	0.0998 (14)
H12A	1.1983	1.4462	0.2048	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0451 (4)	0.0715 (5)	0.0627 (4)	−0.0175 (3)	0.0085 (3)	−0.0383 (3)
O1	0.0804 (16)	0.0857 (16)	0.0912 (17)	−0.0079 (13)	0.0043 (13)	−0.0321 (13)
N1	0.0392 (10)	0.0621 (13)	0.0632 (13)	−0.0114 (9)	0.0033 (9)	−0.0356 (11)
N2	0.0465 (11)	0.0562 (12)	0.0558 (12)	−0.0114 (9)	0.0040 (9)	−0.0297 (10)
N3	0.0449 (11)	0.0497 (11)	0.0517 (11)	−0.0064 (9)	−0.0046 (9)	−0.0224 (9)
C1	0.0458 (13)	0.0696 (17)	0.0714 (17)	0.0026 (12)	−0.0100 (12)	−0.0367 (14)
C2	0.0588 (17)	0.0698 (18)	0.080 (2)	0.0069 (14)	−0.0050 (14)	−0.0408 (16)
C3	0.0659 (17)	0.0668 (17)	0.0567 (15)	−0.0117 (13)	0.0023 (12)	−0.0358 (13)
C4	0.0588 (16)	0.0810 (19)	0.0509 (15)	−0.0058 (14)	−0.0093 (12)	−0.0291 (14)
C5	0.0469 (13)	0.0639 (16)	0.0506 (13)	0.0039 (11)	−0.0055 (10)	−0.0250 (12)
C6	0.0409 (12)	0.0486 (13)	0.0485 (12)	−0.0100 (9)	0.0030 (9)	−0.0218 (10)
C7	0.0432 (12)	0.0442 (12)	0.0447 (12)	−0.0016 (9)	−0.0037 (9)	−0.0181 (10)
C8	0.0529 (14)	0.0518 (14)	0.0527 (14)	−0.0025 (11)	−0.0055 (11)	−0.0243 (11)
C9	0.0546 (14)	0.0513 (14)	0.0539 (14)	−0.0039 (11)	−0.0121 (11)	−0.0221 (11)
C10	0.0736 (18)	0.0454 (14)	0.0765 (18)	0.0006 (12)	−0.0211 (14)	−0.0340 (13)
C11	0.100 (3)	0.0519 (18)	0.150 (4)	−0.0202 (18)	−0.068 (3)	−0.014 (2)
C12	0.058 (2)	0.081 (2)	0.130 (4)	−0.0138 (18)	−0.002 (2)	0.007 (2)

Geometric parameters (Å, º)

S1—C7	1.692 (2)	C3—C4	1.380 (4)
O1—C9	1.356 (4)	C3—H3B	0.9300
O1—C12	1.407 (5)	C4—C5	1.388 (4)
N1—C7	1.345 (3)	C4—H4A	0.9300
N1—C6	1.432 (3)	C5—C6	1.392 (4)
N1—H1A	0.8600	C5—H5A	0.9300
N2—C7	1.347 (3)	C8—C9	1.433 (4)
N2—N3	1.381 (3)	C8—H8A	0.9300
N2—H2A	0.8600	C9—C10	1.349 (3)
N3—C8	1.280 (3)	C10—C11	1.428 (6)
C1—C6	1.379 (4)	C10—H10A	0.9300
C1—C2	1.395 (4)	C11—C12	1.301 (6)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.381 (4)	C12—H12A	0.9300
C2—H2B	0.9300
C9—O1—C12	104.8 (3)	C6—C5—H5A	120.3
C7—N1—C6	127.21 (19)	C1—C6—C5	120.7 (2)
C7—N1—H1A	116.4	C1—C6—N1	118.3 (2)
C6—N1—H1A	116.4	C5—C6—N1	120.9 (2)
C7—N2—N3	120.0 (2)	N1—C7—N2	114.9 (2)
C7—N2—H2A	120.0	N1—C7—S1	125.35 (17)
N3—N2—H2A	120.0	N2—C7—S1	119.72 (18)
C8—N3—N2	116.5 (2)	N3—C8—C9	120.8 (2)
C6—C1—C2	119.3 (3)	N3—C8—H8A	119.6
C6—C1—H1B	120.4	C9—C8—H8A	119.6
C2—C1—H1B	120.4	C10—C9—O1	111.9 (3)
C3—C2—C1	120.4 (3)	C10—C9—C8	124.7 (3)
C3—C2—H2B	119.8	O1—C9—C8	123.5 (2)
C1—C2—H2B	119.8	C9—C10—C11	104.6 (3)
C4—C3—C2	120.0 (2)	C9—C10—H10A	127.7
C4—C3—H3B	120.0	C11—C10—H10A	127.7
C2—C3—H3B	120.0	C12—C11—C10	108.9 (3)
C3—C4—C5	120.2 (2)	C12—C11—H11A	125.6
C3—C4—H4A	119.9	C10—C11—H11A	125.6
C5—C4—H4A	119.9	C11—C12—O1	109.9 (3)
C4—C5—C6	119.4 (2)	C11—C12—H12A	125.1
C4—C5—H5A	120.3	O1—C12—H12A	125.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.19	2.607 (3)	109
N2—H2A···S1^i	0.86	2.54	3.382 (2)	166

Symmetry code: (i) −x, −y+2, −z+1.