1-(5-Chloro-6-fluoro-1,3-benzothia-zol-2-yl)hydrazine.

In the title compound, C(7)H(5)ClFN(3)S, the 1,3-benzothia-zole ring system is nearly planar (r.m.s. deviation = 0.023 Å). In the crystal, mol-ecules are linked via inter-molecular N-H⋯N hydrogen bonds into a two-dimensional network parallel to (100).

Related literature

For general background to and the biological activities of benzothia­zole derivatives, see: Yaseen et al. (2006 ▶); Kini et al. (2007 ▶); Munirajasekhar et al. (2011 ▶); Gurupadayya et al. (2008 ▶); Bowyer et al. (2007 ▶); Mittal et al. (2007 ▶); Pozas et al. (2005 ▶); Rana et al. (2008 ▶). For a related structure, see: Fun et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C7H5ClFN3S

M = 217.65

Monoclinic,

a = 11.1287 (6) Å

b = 5.6641 (3) Å

c = 13.3419 (7) Å

β = 108.552 (1)°

V = 797.29 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 100 K

0.31 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.813, T max = 0.908

9459 measured reflections

2899 independent reflections

2638 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.066

S = 1.07

2899 reflections

138 parameters

All H-atom parameters refined

Δρmax = 0.53 e Å−3

Δρmin = −0.20 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203156X/sj5255sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203156X/sj5255Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203156X/sj5255Isup3.cml

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

C7H5ClFN3S	F(000) = 440
Mr = 217.65	Dx = 1.813 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5638 reflections
a = 11.1287 (6) Å	θ = 3.9–32.6°
b = 5.6641 (3) Å	µ = 0.70 mm−1
c = 13.3419 (7) Å	T = 100 K
β = 108.552 (1)°	Block, colourless
V = 797.29 (7) Å3	0.31 × 0.16 × 0.14 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	2899 independent reflections
Radiation source: fine-focus sealed tube	2638 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 32.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.813, Tmax = 0.908	k = −8→8
9459 measured reflections	l = −20→20

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	All H-atom parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0319P)2 + 0.296P] where P = (Fo2 + 2Fc2)/3
2899 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.17661 (2)	0.55946 (4)	0.127235 (17)	0.01252 (6)
F1	0.45495 (6)	0.83076 (11)	−0.09724 (5)	0.01932 (13)
Cl1	0.40693 (2)	0.42019 (4)	−0.236217 (18)	0.01702 (6)
N1	0.13780 (7)	0.19036 (15)	0.00140 (6)	0.01316 (14)
N2	0.02947 (8)	0.17861 (16)	0.12535 (6)	0.01531 (15)
N3	−0.01178 (8)	0.31566 (15)	0.19707 (6)	0.01435 (15)
C1	0.25396 (8)	0.54873 (16)	0.03242 (7)	0.01196 (15)
C2	0.33315 (8)	0.71802 (17)	0.01037 (7)	0.01342 (15)
C3	0.37807 (8)	0.67098 (17)	−0.07310 (7)	0.01365 (16)
C4	0.34704 (8)	0.46473 (17)	−0.13335 (7)	0.01302 (15)
C5	0.26897 (8)	0.29589 (17)	−0.11025 (7)	0.01283 (15)
C6	0.22136 (8)	0.33884 (16)	−0.02676 (7)	0.01158 (15)
C7	0.10783 (8)	0.28418 (17)	0.08008 (7)	0.01228 (15)
H2A	0.3595 (12)	0.862 (3)	0.0500 (11)	0.014 (3)*
H5A	0.2461 (12)	0.158 (3)	−0.1530 (11)	0.015 (3)*
H1N2	−0.0159 (14)	0.073 (3)	0.0922 (12)	0.023 (4)*
H1N3	−0.0937 (14)	0.360 (3)	0.1679 (12)	0.023 (4)*
H2N3	−0.0068 (14)	0.231 (3)	0.2508 (12)	0.025 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01537 (10)	0.01201 (11)	0.01173 (10)	−0.00092 (7)	0.00648 (7)	−0.00130 (7)
F1	0.0220 (3)	0.0177 (3)	0.0227 (3)	−0.0073 (2)	0.0133 (2)	−0.0019 (2)
Cl1	0.01930 (11)	0.01979 (12)	0.01571 (10)	−0.00142 (8)	0.01083 (8)	−0.00148 (8)
N1	0.0149 (3)	0.0130 (3)	0.0136 (3)	−0.0015 (3)	0.0075 (3)	−0.0013 (3)
N2	0.0196 (4)	0.0146 (4)	0.0155 (3)	−0.0048 (3)	0.0108 (3)	−0.0036 (3)
N3	0.0165 (3)	0.0160 (4)	0.0128 (3)	0.0018 (3)	0.0079 (3)	0.0001 (3)
C1	0.0131 (3)	0.0121 (4)	0.0113 (3)	0.0002 (3)	0.0048 (3)	−0.0004 (3)
C2	0.0149 (4)	0.0121 (4)	0.0142 (4)	−0.0013 (3)	0.0060 (3)	−0.0008 (3)
C3	0.0133 (3)	0.0136 (4)	0.0153 (4)	−0.0018 (3)	0.0062 (3)	0.0007 (3)
C4	0.0134 (3)	0.0150 (4)	0.0122 (3)	0.0010 (3)	0.0063 (3)	0.0002 (3)
C5	0.0134 (3)	0.0136 (4)	0.0124 (3)	0.0004 (3)	0.0054 (3)	−0.0007 (3)
C6	0.0124 (3)	0.0112 (4)	0.0118 (3)	0.0003 (3)	0.0047 (3)	−0.0002 (3)
C7	0.0133 (3)	0.0120 (4)	0.0121 (3)	−0.0004 (3)	0.0050 (3)	0.0003 (3)

S1—C1	1.7429 (9)	N3—H2N3	0.849 (17)
S1—C7	1.7625 (10)	C1—C2	1.3957 (13)
F1—C3	1.3529 (11)	C1—C6	1.4093 (13)
Cl1—C4	1.7243 (9)	C2—C3	1.3839 (12)
N1—C7	1.3109 (11)	C2—H2A	0.966 (15)
N1—C6	1.3912 (11)	C3—C4	1.3977 (13)
N2—C7	1.3483 (11)	C4—C5	1.3910 (13)
N2—N3	1.4172 (11)	C5—C6	1.3986 (12)
N2—H1N2	0.815 (16)	C5—H5A	0.951 (14)
N3—H1N3	0.905 (15)
C1—S1—C7	88.21 (4)	F1—C3—C4	118.78 (8)
C7—N1—C6	109.48 (8)	C2—C3—C4	122.51 (9)
C7—N2—N3	117.01 (8)	C5—C4—C3	120.30 (8)
C7—N2—H1N2	117.3 (11)	C5—C4—Cl1	120.18 (7)
N3—N2—H1N2	119.3 (11)	C3—C4—Cl1	119.52 (7)
N2—N3—H1N3	111.1 (10)	C4—C5—C6	118.59 (8)
N2—N3—H2N3	108.3 (11)	C4—C5—H5A	119.8 (8)
H1N3—N3—H2N3	107.7 (14)	C6—C5—H5A	121.5 (8)
C2—C1—C6	121.92 (8)	N1—C6—C5	124.41 (8)
C2—C1—S1	128.31 (7)	N1—C6—C1	115.70 (8)
C6—C1—S1	109.73 (7)	C5—C6—C1	119.85 (8)
C3—C2—C1	116.83 (9)	N1—C7—N2	122.99 (9)
C3—C2—H2A	118.6 (8)	N1—C7—S1	116.89 (7)
C1—C2—H2A	124.6 (8)	N2—C7—S1	120.11 (7)
F1—C3—C2	118.72 (8)
C7—S1—C1—C2	177.55 (9)	C7—N1—C6—C1	−0.18 (11)
C7—S1—C1—C6	0.05 (7)	C4—C5—C6—N1	176.84 (8)
C6—C1—C2—C3	0.32 (13)	C4—C5—C6—C1	−0.63 (13)
S1—C1—C2—C3	−176.91 (7)	C2—C1—C6—N1	−177.63 (8)
C1—C2—C3—F1	179.88 (8)	S1—C1—C6—N1	0.06 (10)
C1—C2—C3—C4	−0.13 (14)	C2—C1—C6—C5	0.06 (14)
F1—C3—C4—C5	179.54 (8)	S1—C1—C6—C5	177.75 (7)
C2—C3—C4—C5	−0.45 (14)	C6—N1—C7—N2	−179.09 (8)
F1—C3—C4—Cl1	−0.12 (12)	C6—N1—C7—S1	0.22 (10)
C2—C3—C4—Cl1	179.89 (7)	N3—N2—C7—N1	−169.63 (8)
C3—C4—C5—C6	0.82 (13)	N3—N2—C7—S1	11.09 (11)
Cl1—C4—C5—C6	−179.52 (7)	C1—S1—C7—N1	−0.16 (8)
C7—N1—C6—C5	−177.75 (8)	C1—S1—C7—N2	179.17 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.816 (16)	2.132 (16)	2.9478 (12)	176.9 (16)
N3—H2N3···N3ii	0.850 (16)	2.443 (17)	3.1382 (12)	139.5 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.816 (16)	2.132 (16)	2.9478 (12)	176.9 (16)
N3—H2N3⋯N3ii	0.850 (16)	2.443 (17)	3.1382 (12)	139.5 (14)

Symmetry codes: (i) ; (ii) .