6-Nitro-1,3-benzoxazole-2(3H)-thione

In the title compound, C₇H₄N₂O₃S, the dihedral angle between the fused ring system (r.m.s. deviation = 0.008 Å) and the nitro group at the 6-position is 7.3 (2)°. In the crystal, bifurcated N—H...(O,O) hydrogen bonds link the mol­ecules into [010] chains. The chains are cross-linked by π–π stacking inter­actions to form (001) sheets.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.110
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1       --C1       .        5.9 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N2 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.023 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             107.7 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXTL2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: WinGX and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

6-Nitro-1,3-benzoxazole-2(3H)-thione

Crystal data

C7H4N2O3S	F(000) = 400
Mr = 196.18	Dx = 1.651 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.576 (4) Å	Cell parameters from 1870 reflections
b = 15.755 (13) Å	θ = 2.6–27.9°
c = 11.134 (9) Å	µ = 0.38 mm^−1
β = 100.45 (3)°	T = 296 K
V = 789.3 (11) Å^3	Block, yellow
Z = 4	0.35 × 0.28 × 0.21 mm

Data collection

Bruker D8 VENTURE Super DUO diffractometer	1870 independent reflections
Radiation source: INCOATEC IµS micro-focus source	1538 reflections with I > 2σ(I)
HELIOS mirror optics monochromator	Rint = 0.032
Detector resolution: 10.4167 pixels mm^-1	θmax = 27.9°, θmin = 2.6°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −20→20
Tmin = 0.668, Tmax = 0.747	l = −14→14
17038 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 0.3797P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
1870 reflections	Δρmax = 0.30 e Å^−3
118 parameters	Δρmin = −0.26 e Å^−3
0 restraints

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	1.18641 (11)	0.72656 (3)	0.51464 (5)	0.05120 (19)
O1	0.8774 (3)	0.58902 (7)	0.44023 (12)	0.0400 (3)
O2	0.2383 (5)	0.33844 (10)	0.26846 (17)	0.0859 (7)
O3	−0.1051 (4)	0.39654 (11)	0.1403 (2)	0.0766 (6)
N1	0.7184 (3)	0.70175 (9)	0.33226 (14)	0.0374 (3)
H1	0.688902	0.753157	0.314460	0.045*
N2	0.1258 (4)	0.40037 (11)	0.21413 (16)	0.0500 (4)
C1	0.9228 (4)	0.67448 (11)	0.42680 (16)	0.0360 (4)
C2	0.6377 (4)	0.56547 (10)	0.35289 (15)	0.0325 (4)
C3	0.5143 (4)	0.48630 (11)	0.33371 (16)	0.0383 (4)
H3	0.586671	0.439175	0.380032	0.046*
C4	0.2721 (4)	0.48278 (11)	0.23917 (17)	0.0379 (4)
C5	0.1602 (4)	0.55204 (13)	0.16860 (18)	0.0429 (4)
H5	−0.004636	0.545447	0.106807	0.051*
C6	0.2929 (4)	0.63094 (12)	0.18979 (18)	0.0425 (4)
H6	0.223268	0.678035	0.142831	0.051*
C7	0.5340 (4)	0.63613 (10)	0.28427 (16)	0.0331 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0455 (3)	0.0438 (3)	0.0604 (4)	−0.0078 (2)	−0.0005 (2)	−0.0129 (2)
O1	0.0442 (7)	0.0267 (6)	0.0445 (7)	0.0005 (5)	−0.0042 (5)	0.0015 (5)
O2	0.1327 (18)	0.0374 (8)	0.0735 (12)	−0.0331 (10)	−0.0189 (11)	0.0090 (8)
O3	0.0572 (10)	0.0574 (10)	0.1077 (15)	−0.0142 (8)	−0.0056 (10)	−0.0284 (10)
N1	0.0369 (8)	0.0232 (6)	0.0508 (9)	0.0024 (6)	0.0043 (6)	0.0038 (6)
N2	0.0596 (11)	0.0418 (9)	0.0495 (10)	−0.0154 (8)	0.0120 (8)	−0.0138 (8)
C1	0.0364 (9)	0.0285 (8)	0.0437 (10)	0.0021 (7)	0.0093 (7)	−0.0027 (7)
C2	0.0345 (8)	0.0279 (8)	0.0343 (8)	0.0019 (6)	0.0044 (7)	−0.0001 (6)
C3	0.0493 (10)	0.0257 (8)	0.0392 (9)	−0.0012 (7)	0.0061 (8)	0.0015 (7)
C4	0.0428 (9)	0.0308 (8)	0.0419 (10)	−0.0062 (7)	0.0125 (8)	−0.0071 (7)
C5	0.0378 (9)	0.0453 (10)	0.0432 (10)	0.0001 (8)	0.0009 (8)	−0.0049 (8)
C6	0.0422 (10)	0.0351 (9)	0.0471 (10)	0.0049 (7)	−0.0005 (8)	0.0053 (8)
C7	0.0332 (8)	0.0248 (7)	0.0418 (9)	0.0023 (6)	0.0078 (7)	0.0015 (6)

Geometric parameters (Å, º)

S1—C1	1.630 (2)	C2—C3	1.370 (3)
O1—C1	1.375 (2)	C2—C7	1.384 (2)
O1—C2	1.378 (2)	C3—C4	1.384 (3)
O2—N2	1.212 (3)	C3—H3	0.9300
O3—N2	1.217 (3)	C4—C5	1.387 (3)
N1—C1	1.346 (2)	C5—C6	1.385 (3)
N1—C7	1.379 (2)	C5—H5	0.9300
N1—H1	0.8389	C6—C7	1.382 (3)
N2—C4	1.464 (2)	C6—H6	0.9300
C1—O1—C2	107.67 (13)	C2—C3—H3	123.0
C1—N1—C7	110.69 (15)	C4—C3—H3	123.0
C1—N1—H1	123.5	C3—C4—C5	124.17 (17)
C7—N1—H1	124.8	C3—C4—N2	117.11 (17)
O2—N2—O3	122.37 (19)	C5—C4—N2	118.72 (18)
O2—N2—C4	118.72 (19)	C6—C5—C4	120.28 (18)
O3—N2—C4	118.91 (19)	C6—C5—H5	119.9
N1—C1—O1	107.49 (14)	C4—C5—H5	119.9
N1—C1—S1	129.98 (14)	C7—C6—C5	116.58 (17)
O1—C1—S1	122.54 (13)	C7—C6—H6	121.7
C3—C2—O1	127.43 (15)	C5—C6—H6	121.7
C3—C2—C7	123.77 (17)	N1—C7—C6	133.39 (16)
O1—C2—C7	108.80 (15)	N1—C7—C2	105.34 (16)
C2—C3—C4	113.92 (16)	C6—C7—C2	121.27 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.84	2.41	3.068 (3)	135
N1—H1···O3^i	0.84	2.36	3.137 (3)	154

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.