Crystal structure, Hirshfeld surface and crystal void analysis, inter­molecular inter­action energies, DFT calculations and energy frameworks of 2H-benzo[b][1,4]thia­zin-3(4H)-one 1,1-dioxide

In the title compound, the thia­zine ring exhibits a screw-boat conformation. In the crystal, corrugated layers of mol­ecules parallel to the ab plane are formed by N—H...O and C—H...O hydrogen bonds together with C—H...π(ring) and S=O...π(ring) inter­actions. The layers are connected by additional C—H...O hydrogen bonds and π-stacking inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 125 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.025
• wR factor = 0.074
• Data-to-parameter ratio = 32.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

2H-Benzo[b][1,4]thiazin-3(4H)-one 1,1-dioxide

Crystal data

C8H7NO3S	F(000) = 408
Mr = 197.21	Dx = 1.606 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2179 (6) Å	Cell parameters from 9215 reflections
b = 9.5043 (8) Å	θ = 2.9–36.4°
c = 11.9945 (9) Å	µ = 0.37 mm^−1
β = 97.584 (2)°	T = 125 K
V = 815.64 (11) Å^3	Prism, colourless
Z = 4	0.39 × 0.21 × 0.16 mm

Data collection

Bruker D8 QUEST PHOTON 3 diffractometer	3957 independent reflections
Radiation source: fine-focus sealed tube	3739 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 7.3910 pixels mm^-1	θmax = 36.4°, θmin = 3.6°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→15
Tmin = 0.91, Tmax = 0.94	l = −19→20
47688 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: mixed
wR(F^2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.2724P] where P = (Fo^2 + 2Fc^2)/3
3957 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.52 e Å^−3
1 restraint	Δρmin = −0.36 e Å^−3

Special details

Experimental. The diffraction data were obtained from 9 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was 15 sec/frame.

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	0.16068 (2)	0.52143 (2)	0.71754 (2)	0.01099 (4)
O1	0.61228 (8)	0.59530 (6)	0.90859 (5)	0.01991 (10)
O2	0.16268 (8)	0.66721 (6)	0.68352 (5)	0.01797 (10)
O3	−0.01882 (7)	0.45794 (7)	0.72667 (5)	0.01832 (10)
N1	0.57806 (8)	0.47975 (6)	0.74211 (5)	0.01411 (10)
H1	0.7001 (12)	0.4900 (15)	0.7398 (13)	0.027 (3)*
C1	0.27959 (8)	0.42044 (6)	0.62800 (5)	0.01059 (9)
C2	0.17997 (9)	0.35615 (7)	0.53412 (5)	0.01342 (10)
H2	0.047397	0.361237	0.521776	0.016*
C3	0.27651 (11)	0.28460 (7)	0.45882 (6)	0.01663 (11)
H3	0.210847	0.242727	0.393292	0.020*
C4	0.47092 (11)	0.27481 (8)	0.48036 (6)	0.01841 (12)
H4	0.536825	0.224837	0.429380	0.022*
C5	0.56985 (10)	0.33681 (8)	0.57499 (6)	0.01630 (11)
H5	0.701938	0.327605	0.588942	0.020*
C6	0.47486 (8)	0.41274 (7)	0.64966 (5)	0.01164 (10)
C7	0.51172 (9)	0.53288 (7)	0.83499 (5)	0.01315 (10)
C8	0.30863 (9)	0.50214 (7)	0.84603 (5)	0.01299 (10)
H8A	0.266578	0.566751	0.902374	0.016*
H8B	0.298167	0.404753	0.873825	0.016*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.00776 (7)	0.01295 (7)	0.01219 (7)	0.00109 (4)	0.00109 (4)	−0.00153 (4)
O1	0.0173 (2)	0.0236 (3)	0.0174 (2)	−0.00682 (19)	−0.00298 (17)	−0.00209 (18)
O2	0.0205 (2)	0.0129 (2)	0.0200 (2)	0.00460 (17)	0.00061 (18)	0.00015 (16)
O3	0.00783 (18)	0.0262 (3)	0.0214 (2)	−0.00199 (17)	0.00373 (16)	−0.00439 (19)
N1	0.0078 (2)	0.0195 (2)	0.0149 (2)	−0.00112 (17)	0.00092 (16)	0.00008 (18)
C1	0.0092 (2)	0.0114 (2)	0.0113 (2)	0.00061 (16)	0.00190 (16)	−0.00003 (16)
C2	0.0138 (2)	0.0137 (2)	0.0125 (2)	−0.00096 (19)	0.00073 (18)	−0.00101 (18)
C3	0.0212 (3)	0.0150 (3)	0.0140 (2)	−0.0010 (2)	0.0038 (2)	−0.00282 (19)
C4	0.0218 (3)	0.0166 (3)	0.0184 (3)	0.0025 (2)	0.0088 (2)	−0.0024 (2)
C5	0.0133 (2)	0.0177 (3)	0.0190 (3)	0.0033 (2)	0.0064 (2)	0.0004 (2)
C6	0.0093 (2)	0.0130 (2)	0.0130 (2)	0.00103 (17)	0.00242 (17)	0.00133 (17)
C7	0.0114 (2)	0.0143 (2)	0.0133 (2)	−0.00146 (18)	−0.00035 (18)	0.00154 (18)
C8	0.0115 (2)	0.0162 (2)	0.0113 (2)	−0.00114 (19)	0.00154 (18)	−0.00122 (18)

Geometric parameters (Å, º)

S1—O2	1.4450 (6)	C2—H2	0.9500
S1—O3	1.4464 (6)	C3—C4	1.3960 (11)
S1—C1	1.7478 (6)	C3—H3	0.9500
S1—C8	1.7649 (7)	C4—C5	1.3898 (11)
O1—C7	1.2203 (8)	C4—H4	0.9500
N1—C7	1.3661 (9)	C5—C6	1.3982 (9)
N1—C6	1.4043 (9)	C5—H5	0.9500
N1—H1	0.890 (8)	C7—C8	1.5175 (9)
C1—C2	1.3945 (9)	C8—H8A	0.9900
C1—C6	1.4010 (9)	C8—H8B	0.9900
C2—C3	1.3892 (10)
O2—S1—O3	117.64 (4)	C5—C4—C3	121.22 (6)
O2—S1—C1	109.21 (3)	C5—C4—H4	119.4
O3—S1—C1	109.56 (3)	C3—C4—H4	119.4
O2—S1—C8	108.59 (3)	C4—C5—C6	119.96 (6)
O3—S1—C8	109.59 (3)	C4—C5—H5	120.0
C1—S1—C8	100.95 (3)	C6—C5—H5	120.0
C7—N1—C6	127.24 (6)	C5—C6—C1	118.33 (6)
C7—N1—H1	116.1 (10)	C5—C6—N1	119.08 (6)
C6—N1—H1	116.7 (10)	C1—C6—N1	122.58 (6)
C2—C1—C6	121.72 (6)	O1—C7—N1	122.05 (6)
C2—C1—S1	119.61 (5)	O1—C7—C8	121.31 (6)
C6—C1—S1	118.58 (5)	N1—C7—C8	116.53 (6)
C3—C2—C1	119.34 (6)	C7—C8—S1	112.57 (4)
C3—C2—H2	120.3	C7—C8—H8A	109.1
C1—C2—H2	120.3	S1—C8—H8A	109.1
C2—C3—C4	119.38 (6)	C7—C8—H8B	109.1
C2—C3—H3	120.3	S1—C8—H8B	109.1
C4—C3—H3	120.3	H8A—C8—H8B	107.8
O2—S1—C1—C2	−93.69 (6)	C2—C1—C6—C5	−0.74 (9)
O3—S1—C1—C2	36.48 (6)	S1—C1—C6—C5	−177.28 (5)
C8—S1—C1—C2	152.03 (5)	C2—C1—C6—N1	178.32 (6)
O2—S1—C1—C6	82.92 (6)	S1—C1—C6—N1	1.78 (8)
O3—S1—C1—C6	−146.91 (5)	C7—N1—C6—C5	−165.40 (7)
C8—S1—C1—C6	−31.36 (6)	C7—N1—C6—C1	15.55 (10)
C6—C1—C2—C3	−1.16 (10)	C6—N1—C7—O1	−176.50 (7)
S1—C1—C2—C3	175.34 (5)	C6—N1—C7—C8	7.37 (10)
C1—C2—C3—C4	1.92 (10)	O1—C7—C8—S1	141.26 (6)
C2—C3—C4—C5	−0.81 (11)	N1—C7—C8—S1	−42.58 (7)
C3—C4—C5—C6	−1.12 (11)	O2—S1—C8—C7	−64.45 (5)
C4—C5—C6—C1	1.86 (10)	O3—S1—C8—C7	165.81 (5)
C4—C5—C6—N1	−177.23 (6)	C1—S1—C8—C7	50.29 (5)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.89 (1)	2.08 (1)	2.9472 (8)	165 (1)
C5—H5···O1^ii	0.95	2.58	3.2330 (9)	126
C8—H8A···Cg2^iii	0.99	2.93	3.7933 (8)	146
C8—H8B···O2^iv	0.99	2.39	3.2126 (9)	140

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