5-(4-Fluoro­phen­yl)-1,3,4-thia­diazol-2-ylamine

The title compound, C₈H₆FN₃S, was synthesized by the reaction of 4-fluoro­benzoic acid and thio­semicarbazide. The two H atoms of the amine are involved in N—H...N hydrogen bonding, resulting in the formation of layers parallel to the (100) plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.133
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.03
PLAT322_ALERT_2_C Check Hybridisation of  S      in Main Residue .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-ylamine

Crystal data

C8H6FN3S	F(000) = 400
Mr = 195.22	Dx = 1.502 Mg m^−3
Monoclinic, P21/c	Melting point: 513 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8020 (18) Å	Cell parameters from 25 reflections
b = 8.9610 (18) Å	θ = 10–13°
c = 11.035 (2) Å	µ = 0.34 mm^−1
β = 97.19 (3)°	T = 293 K
V = 863.5 (3) Å^3	Plate, yellow
Z = 4	0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1378 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 26.0°, θmin = 2.3°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.875, Tmax = 0.967	l = −13→13
1810 measured reflections	3 standard reflections every 200 reflections
1699 independent reflections	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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0831P)^2 + 0.1422P] where P = (Fo^2 + 2Fc^2)/3
1699 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 7.45–7.48 (m, 2H), 7.05–7.01 (m, 2H), 5.20 (s, 2H).

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
S	0.67382 (8)	0.64217 (7)	0.65161 (5)	0.0479 (2)
F	0.9517 (3)	0.0642 (2)	0.3617 (2)	0.1045 (8)
N1	0.6516 (3)	0.6979 (2)	0.42360 (17)	0.0498 (5)
N2	0.5926 (3)	0.8231 (2)	0.47480 (18)	0.0526 (5)
N3	0.5430 (3)	0.9128 (3)	0.66437 (19)	0.0647 (7)
H3A	0.5042	0.9942	0.6330	0.078*
H3B	0.5479	0.8979	0.7418	0.078*
C1	0.8926 (4)	0.1949 (3)	0.3983 (3)	0.0659 (8)
C2	0.9109 (3)	0.3208 (4)	0.3321 (3)	0.0634 (7)
H2	0.9639	0.3178	0.2644	0.076*
C3	0.8490 (3)	0.4523 (3)	0.3681 (2)	0.0545 (6)
H3	0.8611	0.5396	0.3247	0.065*
C4	0.7685 (3)	0.4555 (3)	0.4690 (2)	0.0434 (5)
C5	0.7544 (3)	0.3254 (3)	0.5345 (2)	0.0541 (6)
H5	0.7034	0.3274	0.6034	0.065*
C6	0.8154 (4)	0.1928 (3)	0.4984 (3)	0.0682 (8)
H6	0.8042	0.1047	0.5410	0.082*
C7	0.6987 (3)	0.5958 (3)	0.50219 (19)	0.0421 (5)
C8	0.5957 (3)	0.8094 (3)	0.5929 (2)	0.0454 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0684 (4)	0.0426 (4)	0.0327 (3)	0.0115 (3)	0.0057 (3)	0.0049 (2)
F	0.1419 (19)	0.0732 (13)	0.1000 (15)	0.0494 (13)	0.0213 (13)	−0.0206 (11)
N1	0.0748 (13)	0.0407 (11)	0.0340 (10)	0.0096 (10)	0.0075 (9)	0.0009 (8)
N2	0.0832 (15)	0.0391 (11)	0.0347 (10)	0.0134 (10)	0.0045 (10)	0.0031 (8)
N3	0.1062 (19)	0.0526 (13)	0.0340 (10)	0.0287 (13)	0.0030 (11)	−0.0025 (9)
C1	0.0777 (19)	0.0557 (16)	0.0631 (17)	0.0241 (15)	0.0043 (14)	−0.0160 (14)
C2	0.0644 (17)	0.0737 (19)	0.0531 (15)	0.0136 (14)	0.0112 (13)	−0.0101 (14)
C3	0.0628 (16)	0.0521 (15)	0.0492 (14)	0.0045 (12)	0.0097 (12)	0.0011 (11)
C4	0.0495 (13)	0.0405 (12)	0.0395 (11)	0.0032 (10)	0.0021 (9)	−0.0027 (10)
C5	0.0695 (16)	0.0432 (14)	0.0503 (14)	0.0091 (12)	0.0111 (12)	0.0047 (11)
C6	0.091 (2)	0.0430 (14)	0.0710 (18)	0.0145 (14)	0.0110 (16)	0.0054 (13)
C7	0.0540 (13)	0.0379 (12)	0.0337 (11)	0.0014 (10)	0.0031 (9)	0.0007 (9)
C8	0.0609 (14)	0.0388 (12)	0.0351 (11)	0.0076 (10)	0.0003 (10)	0.0021 (9)

Geometric parameters (Å, º)

S—C8	1.740 (2)	C1—C6	1.368 (4)
S—C7	1.741 (2)	C2—C3	1.378 (4)
F—C1	1.363 (3)	C2—H2	0.9300
N1—C7	1.293 (3)	C3—C4	1.392 (3)
N1—N2	1.386 (3)	C3—H3	0.9300
N2—C8	1.306 (3)	C4—C5	1.385 (3)
N3—C8	1.337 (3)	C4—C7	1.467 (3)
N3—H3A	0.8600	C5—C6	1.383 (4)
N3—H3B	0.8600	C5—H5	0.9300
C1—C2	1.364 (4)	C6—H6	0.9300
C8—S—C7	86.75 (11)	C5—C4—C3	119.2 (2)
C7—N1—N2	113.85 (18)	C5—C4—C7	121.5 (2)
C8—N2—N1	111.63 (19)	C3—C4—C7	119.2 (2)
C8—N3—H3A	120.0	C6—C5—C4	120.6 (3)
C8—N3—H3B	120.0	C6—C5—H5	119.7
H3A—N3—H3B	120.0	C4—C5—H5	119.7
F—C1—C2	118.5 (3)	C1—C6—C5	118.1 (3)
F—C1—C6	118.3 (3)	C1—C6—H6	121.0
C2—C1—C6	123.2 (3)	C5—C6—H6	121.0
C1—C2—C3	118.4 (2)	N1—C7—C4	123.3 (2)
C1—C2—H2	120.8	N1—C7—S	113.51 (17)
C3—C2—H2	120.8	C4—C7—S	123.23 (17)
C2—C3—C4	120.4 (2)	N2—C8—N3	123.9 (2)
C2—C3—H3	119.8	N2—C8—S	114.25 (18)
C4—C3—H3	119.8	N3—C8—S	121.82 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N1^i	0.86	2.27	3.065 (3)	155
N3—H3A···N2^ii	0.86	2.14	2.987 (3)	170

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