(E)-1-(2,4-Dichloro­benzyl­idene)thio­semicarbazide

In the crystal structure of the title compound, C₈H₇Cl₂N₃S, the Schiff base is approximately planar. An intra­molecular N—H...S hydrogen bond stabilizes the mol­ecular structure. The mol­ecules are linked by N—H...S and N—H...Cl hydrogen bonds, forming a chain along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.072
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C1      ..       5.64 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  CL1     ..       2.95 Ang.

   0 ALERT level A = In general: serious problem
   0 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
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

(E)-1-(2,4-Dichlorobenzylidene)thiosemicarbazide

Crystal data

C8H7Cl2N3S	Z = 2
Mr = 248.13	F(000) = 252
Triclinic, P1	Dx = 1.611 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.8840 (12) Å	Cell parameters from 1824 reflections
b = 8.1407 (13) Å	θ = 2.6–27.8°
c = 8.3101 (14) Å	µ = 0.80 mm^−1
α = 100.603 (8)°	T = 113 K
β = 101.290 (8)°	Block, colourless
γ = 93.550 (9)°	0.22 × 0.18 × 0.16 mm
V = 511.44 (14) Å^3

Data collection

Rigaku Saturn diffractometer	2411 independent reflections
Radiation source: rotating anode	1860 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.032
Detector resolution: 7.31 pixels mm^-1	θmax = 27.8°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.844, Tmax = 0.883	l = −10→10
6307 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0392P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
2411 reflections	Δρmax = 0.32 e Å^−3
141 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (6)

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
Cl1	0.27717 (6)	0.04297 (5)	0.51954 (5)	0.02956 (15)
Cl2	0.44450 (5)	0.23381 (5)	−0.01707 (4)	0.01858 (12)
S1	0.04947 (5)	0.77161 (4)	1.09708 (5)	0.01505 (12)
N1	0.12433 (18)	0.86165 (17)	0.82603 (18)	0.0185 (3)
N2	0.13221 (16)	0.58437 (15)	0.83655 (15)	0.0132 (3)
N3	0.18089 (15)	0.55800 (16)	0.68523 (15)	0.0143 (3)
C1	0.10287 (18)	0.73955 (18)	0.90792 (18)	0.0129 (3)
C2	0.20699 (19)	0.40743 (19)	0.62849 (18)	0.0139 (3)
H2	0.1891	0.3224	0.6896	0.017*
C3	0.26414 (18)	0.36426 (18)	0.47057 (18)	0.0126 (3)
C4	0.30179 (19)	0.20260 (18)	0.40910 (18)	0.0151 (3)
C5	0.35839 (18)	0.16003 (18)	0.26126 (18)	0.0154 (3)
H5	0.3829	0.0486	0.2224	0.018*
C6	0.37824 (18)	0.28415 (19)	0.17159 (18)	0.0140 (3)
C7	0.34232 (19)	0.44700 (19)	0.22689 (18)	0.0152 (3)
H7	0.3565	0.5309	0.1635	0.018*
C8	0.28602 (18)	0.48579 (18)	0.37445 (18)	0.0150 (3)
H8	0.2614	0.5974	0.4123	0.018*
H1	0.091 (2)	0.957 (2)	0.859 (2)	0.030 (5)*
H3	0.145 (2)	0.833 (2)	0.732 (2)	0.030 (6)*
H4	0.104 (2)	0.504 (2)	0.868 (2)	0.027 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0584 (3)	0.0157 (2)	0.0238 (2)	0.00910 (19)	0.0236 (2)	0.00963 (17)
Cl2	0.0195 (2)	0.0245 (2)	0.0142 (2)	0.00306 (16)	0.00847 (15)	0.00480 (15)
S1	0.0213 (2)	0.01092 (19)	0.0143 (2)	0.00307 (15)	0.00673 (16)	0.00227 (14)
N1	0.0276 (8)	0.0126 (7)	0.0205 (8)	0.0064 (6)	0.0129 (6)	0.0068 (6)
N2	0.0179 (7)	0.0110 (7)	0.0125 (6)	0.0011 (5)	0.0065 (5)	0.0035 (5)
N3	0.0133 (6)	0.0173 (6)	0.0126 (6)	0.0008 (5)	0.0047 (5)	0.0021 (5)
C1	0.0085 (7)	0.0132 (7)	0.0155 (8)	−0.0012 (6)	0.0001 (6)	0.0023 (6)
C2	0.0145 (7)	0.0148 (7)	0.0127 (7)	0.0014 (6)	0.0026 (6)	0.0036 (6)
C3	0.0100 (7)	0.0157 (7)	0.0118 (7)	0.0005 (6)	0.0017 (6)	0.0026 (6)
C4	0.0172 (8)	0.0150 (8)	0.0146 (8)	0.0012 (6)	0.0035 (6)	0.0069 (6)
C5	0.0165 (8)	0.0144 (8)	0.0152 (8)	0.0027 (6)	0.0042 (6)	0.0018 (6)
C6	0.0097 (7)	0.0221 (8)	0.0102 (7)	0.0005 (6)	0.0023 (6)	0.0038 (6)
C7	0.0152 (7)	0.0172 (8)	0.0146 (8)	0.0006 (6)	0.0034 (6)	0.0064 (6)
C8	0.0151 (8)	0.0138 (7)	0.0161 (8)	0.0028 (6)	0.0026 (6)	0.0035 (6)

Geometric parameters (Å, º)

Cl1—C4	1.7453 (14)	C2—H2	0.9500
Cl2—C6	1.7348 (15)	C3—C4	1.393 (2)
S1—C1	1.6847 (15)	C3—C8	1.404 (2)
N1—C1	1.3239 (19)	C4—C5	1.381 (2)
N1—H1	0.846 (19)	C5—C6	1.380 (2)
N1—H3	0.826 (18)	C5—H5	0.9500
N2—C1	1.3474 (18)	C6—C7	1.386 (2)
N2—N3	1.3691 (16)	C7—C8	1.374 (2)
N2—H4	0.783 (17)	C7—H7	0.9500
N3—C2	1.2742 (19)	C8—H8	0.9500
C2—C3	1.4595 (19)
C1—N1—H1	119.6 (13)	C5—C4—C3	122.90 (13)
C1—N1—H3	116.1 (12)	C5—C4—Cl1	117.01 (11)
H1—N1—H3	122.2 (16)	C3—C4—Cl1	120.09 (11)
C1—N2—N3	120.08 (12)	C6—C5—C4	118.00 (14)
C1—N2—H4	122.1 (14)	C6—C5—H5	121.0
N3—N2—H4	116.6 (14)	C4—C5—H5	121.0
C2—N3—N2	115.49 (12)	C5—C6—C7	121.47 (13)
N1—C1—N2	117.12 (13)	C5—C6—Cl2	119.17 (12)
N1—C1—S1	123.20 (12)	C7—C6—Cl2	119.34 (11)
N2—C1—S1	119.63 (11)	C8—C7—C6	119.28 (14)
N3—C2—C3	120.68 (13)	C8—C7—H7	120.4
N3—C2—H2	119.7	C6—C7—H7	120.4
C3—C2—H2	119.7	C7—C8—C3	121.49 (14)
C4—C3—C8	116.86 (13)	C7—C8—H8	119.3
C4—C3—C2	122.09 (13)	C3—C8—H8	119.3
C8—C3—C2	121.04 (13)
C1—N2—N3—C2	179.46 (13)	C3—C4—C5—C6	0.1 (2)
N3—N2—C1—N1	−0.4 (2)	Cl1—C4—C5—C6	179.79 (11)
N3—N2—C1—S1	−177.99 (10)	C4—C5—C6—C7	−0.2 (2)
N2—N3—C2—C3	−178.28 (12)	C4—C5—C6—Cl2	−178.58 (11)
N3—C2—C3—C4	176.88 (14)	C5—C6—C7—C8	0.1 (2)
N3—C2—C3—C8	−2.2 (2)	Cl2—C6—C7—C8	178.52 (11)
C8—C3—C4—C5	0.1 (2)	C6—C7—C8—C3	0.0 (2)
C2—C3—C4—C5	−179.04 (13)	C4—C3—C8—C7	−0.1 (2)
C8—C3—C4—Cl1	−179.63 (11)	C2—C3—C8—C7	178.99 (13)
C2—C3—C4—Cl1	1.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^i	0.846 (19)	2.534 (19)	3.3685 (15)	169.0 (16)
N1—H3···Cl1^ii	0.826 (18)	2.955 (17)	3.5331 (15)	128.9 (15)
N2—H4···S1^iii	0.783 (17)	2.574 (17)	3.3372 (14)	165.1 (17)

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