2-Methyl­thio­semicarbazide

The crystal structure of the title compound, C₂H₇N₃S, displays N—H...S and N—H...N hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](N-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.079
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.822     0.951
            RT(exp) =      1.156
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.16
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3B    ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

For related literature, see [type here to add references to related literature].

Related literature

Stefanic et al. (1990). Is this a previous structure determination?

S2. Refinement

The hydrogen atoms were directly located in the crystallographic study using difference Fourier maps and were refined isotropically.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and publCIF (Westrip, 2007).

Figures

Fig. 1. DIAMOND representation of the assymetric unit of 2-methylthiosemicarbazide. The thermal ellipsoids are shown at the 50% probability level.

2-methylthiosemicarbazide

Crystal data

C2H7N3S	F(000) = 224
Mr = 105.17	Dx = 1.420 Mg m^−3
Monoclinic, P21/n	Melting point: 173 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.6071 (9) Å	Cell parameters from 913 reflections
b = 5.9337 (6) Å	µ = 0.50 mm^−1
c = 9.7415 (10) Å	T = 200 K
β = 98.508 (9)°	Block, colorless
V = 492.04 (9) Å^3	0.4 × 0.4 × 0.1 mm
Z = 4

Data collection

Oxford Xcalibur 3CCD diffractometer	900 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.5°, θmin = 4.5°
ω scans	h = −10→10
4506 measured reflections	k = −7→7
913 independent reflections	l = −11→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0322P)^2 + 0.3245P] where P = (Fo^2 + 2Fc^2)/3
913 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.23 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
H3B	0.776 (3)	0.157 (4)	1.033 (3)	0.049 (7)*
H1B	0.366 (3)	0.151 (4)	0.798 (2)	0.033 (6)*
H1A	0.504 (2)	0.043 (4)	0.862 (2)	0.025 (5)*
H2B	0.809 (3)	0.572 (4)	1.027 (3)	0.046 (7)*
H2A	0.875 (3)	0.546 (4)	0.885 (2)	0.040 (6)*
H2C	0.732 (3)	0.688 (5)	0.891 (3)	0.057 (8)*
H3A	0.837 (3)	0.130 (4)	0.911 (3)	0.041 (7)*
S1	0.44036 (5)	0.59448 (8)	0.76678 (5)	0.02764 (19)
C1	0.5343 (2)	0.3573 (3)	0.83652 (18)	0.0213 (4)
N2	0.68539 (17)	0.3589 (2)	0.89476 (16)	0.0228 (4)
N3	0.7511 (2)	0.1490 (3)	0.9432 (2)	0.0300 (4)
N1	0.4598 (2)	0.1604 (3)	0.83089 (19)	0.0292 (4)
C2	0.7809 (2)	0.5601 (4)	0.9259 (2)	0.0291 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0213 (3)	0.0227 (3)	0.0375 (3)	0.00257 (18)	−0.00012 (19)	0.00346 (19)
C1	0.0196 (9)	0.0221 (9)	0.0225 (9)	0.0003 (7)	0.0044 (7)	−0.0016 (7)
N2	0.0191 (8)	0.0189 (8)	0.0293 (8)	0.0015 (6)	−0.0005 (6)	0.0016 (6)
N3	0.0254 (9)	0.0276 (9)	0.0359 (10)	0.0059 (7)	0.0012 (7)	0.0062 (7)
N1	0.0204 (9)	0.0208 (9)	0.0452 (10)	−0.0025 (7)	0.0003 (7)	0.0010 (7)
C2	0.0217 (10)	0.0277 (11)	0.0363 (11)	−0.0046 (8)	−0.0004 (8)	0.0009 (9)

Geometric parameters (Å, º)

S1—C1	1.7128 (18)	N3—H3A	0.85 (3)
C1—N1	1.330 (2)	N1—H1B	0.82 (2)
C1—N2	1.340 (2)	N1—H1A	0.83 (2)
N2—N3	1.420 (2)	C2—H2B	0.98 (3)
N2—C2	1.456 (2)	C2—H2A	0.95 (2)
N3—H3B	0.87 (3)	C2—H2C	0.91 (3)
N1—C1—N2	117.09 (16)	C1—N1—H1B	120.8 (16)
N1—C1—S1	120.63 (14)	C1—N1—H1A	122.2 (15)
N2—C1—S1	122.25 (13)	H1B—N1—H1A	117 (2)
C1—N2—N3	116.65 (15)	N2—C2—H2B	108.5 (14)
C1—N2—C2	125.24 (15)	N2—C2—H2A	109.2 (15)
N3—N2—C2	117.73 (14)	H2B—C2—H2A	109 (2)
N2—N3—H3B	108.3 (17)	N2—C2—H2C	112.9 (17)
N2—N3—H3A	108.5 (16)	H2B—C2—H2C	110 (2)
H3B—N3—H3A	106 (2)	H2A—C2—H2C	107 (2)
N1—C1—N2—N3	0.7 (2)	N1—C1—N2—C2	−172.04 (18)
S1—C1—N2—N3	−177.29 (13)	S1—C1—N2—C2	10.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1^i	0.83 (2)	2.84 (2)	3.4150 (18)	127.6 (17)
N1—H1A···N3	0.83 (2)	2.25 (2)	2.584 (3)	104.5 (17)
N1—H1B···S1^ii	0.82 (2)	2.64 (3)	3.4573 (19)	170 (2)
N3—H3A···S1^iii	0.85 (3)	2.77 (3)	3.598 (2)	163 (2)

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+3/2, y−1/2, −z+3/2.