4-Methyl-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one

In the crystal of the title compound, C₉H₉NOS, the mol­ecules are linked by C—H...O hydrogen bonds to generate bilayers lying parallel to (001).

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.076
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B    ..  O1      ..       2.62 Ang.

Alert level G
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1     ..  C7      ..       2.96 Ang.
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Note

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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 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: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-Methyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

Crystal data

C9H9NOS	Dx = 1.400 Mg m^−3
Mr = 179.23	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9930 reflections
a = 7.3148 (6) Å	θ = 3.2–72.4°
b = 8.4030 (6) Å	µ = 2.95 mm^−1
c = 27.670 (2) Å	T = 150 K
V = 1700.8 (2) Å^3	Plate, colourless
Z = 8	0.33 × 0.31 × 0.04 mm
F(000) = 752

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	1674 independent reflections
Radiation source: INCOATEC IµS micro-focus source	1628 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.2°, θmin = 3.2°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
Tmin = 0.63, Tmax = 0.88	l = −34→30
16139 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	All H-atom parameters refined
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.7672P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
1674 reflections	Δρmax = 0.29 e Å^−3
146 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (3)

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.

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.

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

	x	y	z	Uiso*/Ueq
S1	0.70736 (4)	0.30751 (4)	0.62414 (2)	0.02827 (15)
O1	0.44820 (14)	0.32356 (11)	0.50834 (3)	0.0293 (2)
N1	0.36431 (14)	0.44168 (12)	0.57877 (3)	0.0207 (2)
C1	0.55962 (17)	0.44702 (14)	0.65097 (4)	0.0227 (3)
C2	0.59106 (19)	0.50090 (17)	0.69783 (5)	0.0302 (3)
H2	0.693 (2)	0.458 (2)	0.7141 (6)	0.039 (5)*
C3	0.4778 (2)	0.61424 (18)	0.71846 (5)	0.0347 (3)
H3	0.499 (3)	0.652 (2)	0.7512 (7)	0.046 (5)*
C4	0.3350 (2)	0.67709 (18)	0.69178 (5)	0.0320 (3)
H4	0.261 (3)	0.759 (2)	0.7048 (6)	0.047 (5)*
C5	0.29965 (17)	0.62271 (16)	0.64548 (5)	0.0257 (3)
H5	0.195 (2)	0.666 (2)	0.6276 (5)	0.030 (4)*
C6	0.40958 (16)	0.50524 (14)	0.62472 (4)	0.0200 (3)
C7	0.49111 (17)	0.38099 (14)	0.54745 (4)	0.0220 (3)
C8	0.68710 (17)	0.38743 (16)	0.56376 (5)	0.0254 (3)
H8A	0.731 (2)	0.492 (2)	0.5634 (6)	0.033 (4)*
H8B	0.759 (3)	0.319 (2)	0.5421 (6)	0.034 (4)*
C9	0.17297 (18)	0.44689 (17)	0.56278 (5)	0.0280 (3)
H9A	0.095 (2)	0.435 (2)	0.5922 (6)	0.034 (4)*
H9B	0.148 (3)	0.549 (2)	0.5456 (6)	0.043 (5)*
H9C	0.152 (2)	0.359 (2)	0.5394 (6)	0.033 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0234 (2)	0.0272 (2)	0.0342 (2)	0.00595 (11)	−0.00356 (11)	0.00232 (12)
O1	0.0317 (5)	0.0301 (5)	0.0261 (5)	−0.0038 (4)	−0.0010 (4)	−0.0083 (4)
N1	0.0175 (5)	0.0229 (5)	0.0217 (5)	0.0001 (4)	−0.0023 (4)	−0.0015 (4)
C1	0.0213 (6)	0.0234 (6)	0.0233 (6)	−0.0027 (5)	−0.0004 (4)	0.0032 (5)
C2	0.0280 (7)	0.0383 (7)	0.0242 (6)	−0.0054 (6)	−0.0050 (5)	0.0052 (5)
C3	0.0367 (8)	0.0469 (8)	0.0206 (6)	−0.0080 (6)	0.0020 (5)	−0.0050 (6)
C4	0.0322 (7)	0.0364 (7)	0.0275 (7)	−0.0012 (6)	0.0074 (6)	−0.0069 (5)
C5	0.0239 (6)	0.0270 (6)	0.0262 (6)	0.0010 (5)	0.0023 (5)	−0.0006 (5)
C6	0.0194 (6)	0.0214 (6)	0.0192 (6)	−0.0030 (4)	0.0008 (4)	0.0011 (4)
C7	0.0242 (6)	0.0189 (5)	0.0229 (6)	−0.0016 (5)	0.0007 (5)	−0.0012 (4)
C8	0.0209 (6)	0.0269 (6)	0.0283 (6)	0.0000 (5)	0.0018 (5)	−0.0044 (5)
C9	0.0202 (6)	0.0345 (7)	0.0294 (7)	0.0014 (5)	−0.0059 (5)	−0.0028 (6)

Geometric parameters (Å, º)

S1—C1	1.7589 (13)	C3—H3	0.97 (2)
S1—C8	1.8067 (14)	C4—C5	1.3846 (19)
O1—C7	1.2257 (15)	C4—H4	0.94 (2)
N1—C7	1.3680 (16)	C5—C6	1.3967 (17)
N1—C6	1.4183 (15)	C5—H5	0.979 (17)
N1—C9	1.4684 (16)	C7—C8	1.5040 (18)
C1—C2	1.3924 (18)	C8—H8A	0.937 (19)
C1—C6	1.4042 (17)	C8—H8B	0.983 (18)
C2—C3	1.385 (2)	C9—H9A	0.998 (17)
C2—H2	0.943 (18)	C9—H9B	0.998 (19)
C3—C4	1.384 (2)	C9—H9C	0.995 (17)
C1—S1—C8	95.30 (6)	C5—C6—C1	118.91 (11)
C7—N1—C6	123.36 (10)	C5—C6—N1	120.02 (11)
C7—N1—C9	117.81 (10)	C1—C6—N1	121.00 (11)
C6—N1—C9	118.77 (10)	O1—C7—N1	122.17 (12)
C2—C1—C6	119.84 (12)	O1—C7—C8	121.54 (11)
C2—C1—S1	120.56 (10)	N1—C7—C8	116.29 (10)
C6—C1—S1	119.61 (9)	C7—C8—S1	110.02 (9)
C3—C2—C1	120.56 (13)	C7—C8—H8A	110.9 (10)
C3—C2—H2	122.5 (11)	S1—C8—H8A	109.3 (10)
C1—C2—H2	116.9 (11)	C7—C8—H8B	108.0 (11)
C4—C3—C2	119.59 (13)	S1—C8—H8B	107.6 (10)
C4—C3—H3	119.6 (12)	H8A—C8—H8B	110.9 (14)
C2—C3—H3	120.8 (12)	N1—C9—H9A	107.2 (10)
C3—C4—C5	120.59 (13)	N1—C9—H9B	110.2 (11)
C3—C4—H4	120.4 (12)	H9A—C9—H9B	111.7 (14)
C5—C4—H4	119.0 (12)	N1—C9—H9C	108.8 (10)
C4—C5—C6	120.40 (12)	H9A—C9—H9C	111.4 (14)
C4—C5—H5	119.5 (9)	H9B—C9—H9C	107.6 (13)
C6—C5—H5	120.1 (9)
C8—S1—C1—C2	−145.51 (11)	S1—C1—C6—N1	6.45 (16)
C8—S1—C1—C6	34.01 (11)	C7—N1—C6—C5	152.11 (12)
C6—C1—C2—C3	−1.42 (19)	C9—N1—C6—C5	−25.19 (16)
S1—C1—C2—C3	178.10 (11)	C7—N1—C6—C1	−30.72 (17)
C1—C2—C3—C4	−1.6 (2)	C9—N1—C6—C1	151.98 (12)
C2—C3—C4—C5	2.8 (2)	C6—N1—C7—O1	178.39 (11)
C3—C4—C5—C6	−1.0 (2)	C9—N1—C7—O1	−4.28 (17)
C4—C5—C6—C1	−1.97 (19)	C6—N1—C7—C8	−1.19 (16)
C4—C5—C6—N1	175.26 (11)	C9—N1—C7—C8	176.13 (11)
C2—C1—C6—C5	3.18 (18)	O1—C7—C8—S1	−129.74 (11)
S1—C1—C6—C5	−176.35 (9)	N1—C7—C8—S1	49.85 (13)
C2—C1—C6—N1	−174.02 (11)	C1—S1—C8—C7	−60.08 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1^i	0.983 (18)	2.301 (18)	3.2819 (16)	175.0 (15)
C9—H9B···O1^ii	0.998 (19)	2.62 (2)	3.6157 (17)	173.3 (15)
C9—H9C···O1^iii	0.995 (17)	2.512 (17)	3.4265 (16)	152.6 (14)

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