


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015022276/hb7545sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015022276/hb7545Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015022276/hb7545Isup3.cml |
CCDC reference: 1438105
To a solution of 2H-benzo[b][1,4]thiazin-3(4H)-one (0.543 g, 3.29 mmol), benzyl chloride (0.76 ml, 6.58 mmol) and potassium carbonate (0.91 g, 6.58 mmol) in DMF (15 ml) was added a catalytic amount of tetra- n-butylammonium bromide (0.11 g, 0.33 mmol) and the mixture was stirred for 24 h. The solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from ethanol to afford colorless crystals in 75% yield.
H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.
As a continuation of our research devoted to the development of substituted 1,4-benzothiazine derivatives (Zerzouf et al., 2001; Sebbar et al., 2015), we report the synthesis of a 1,4-benzothiazine derivative by reaction of benzyl chloride with 2H-benzo[b][1,4]thiazin-3(4H)-one in the presence of tetra-n-butylammonium bromide as catalyst and potassium carbonate as base (Scheme 1).
In the title compound, the heterocyclic ring has puckering parameters Q = 0.6272 (10) Å, θ = 63.91 (10)° and φ = 325.56 (11)°. The dihedral angle between the rings C1-C6 and C10-C15 is 86.54 (4)°. Weak C—H···O interactions (Table 1) form chains running parallel to the b axis (Fig. 2).
For related structures and background to 1,4-benzothiazine derivatives, see: Zerzouf et al. (2001); Sebbar et al. (2015).
Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); 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, 2015b).
![]() | Fig. 1. Perspective view of the molecule with 50% probability ellipsoids. |
![]() | Fig. 2. Packing viewed down the b axis. Intermolecular C—H···O interactions are shown by dotted lines. |
C15H13NOS | F(000) = 536 |
Mr = 255.32 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8711 (7) Å | Cell parameters from 9273 reflections |
b = 5.3815 (3) Å | θ = 2.6–29.0° |
c = 21.1997 (13) Å | µ = 0.25 mm−1 |
β = 93.128 (1)° | T = 150 K |
V = 1238.39 (13) Å3 | Block, colourless |
Z = 4 | 0.31 × 0.19 × 0.15 mm |
Bruker SMART APEX CCD diffractometer | 3318 independent reflections |
Radiation source: fine-focus sealed tube | 2731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.1°, θmin = 1.9° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −7→7 |
Tmin = 0.88, Tmax = 0.96 | l = −28→28 |
22588 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0711P)2 + 0.0734P] where P = (Fo2 + 2Fc2)/3 |
3318 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C15H13NOS | V = 1238.39 (13) Å3 |
Mr = 255.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8711 (7) Å | µ = 0.25 mm−1 |
b = 5.3815 (3) Å | T = 150 K |
c = 21.1997 (13) Å | 0.31 × 0.19 × 0.15 mm |
β = 93.128 (1)° |
Bruker SMART APEX CCD diffractometer | 3318 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | 2731 reflections with I > 2σ(I) |
Tmin = 0.88, Tmax = 0.96 | Rint = 0.034 |
22588 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.43 e Å−3 |
3318 reflections | Δρmin = −0.19 e Å−3 |
163 parameters |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 20 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | ||
S1 | 1.01122 (3) | 0.51867 (6) | 0.64271 (2) | 0.02520 (11) | |
O1 | 0.82014 (8) | 0.06255 (17) | 0.72781 (4) | 0.0263 (2) | |
N1 | 0.77044 (9) | 0.22455 (18) | 0.63087 (4) | 0.0188 (2) | |
C1 | 0.78669 (10) | 0.4044 (2) | 0.58307 (5) | 0.0183 (2) | |
C2 | 0.69629 (11) | 0.4345 (2) | 0.53375 (5) | 0.0228 (2) | |
H2 | 0.6216 | 0.3430 | 0.5342 | 0.027* | |
C3 | 0.71505 (12) | 0.5966 (2) | 0.48439 (5) | 0.0266 (3) | |
H3 | 0.6537 | 0.6136 | 0.4510 | 0.032* | |
C4 | 0.82274 (12) | 0.7341 (2) | 0.48348 (5) | 0.0283 (3) | |
H4 | 0.8359 | 0.8435 | 0.4493 | 0.034* | |
C5 | 0.91096 (12) | 0.7109 (3) | 0.53267 (5) | 0.0273 (3) | |
H5 | 0.9839 | 0.8080 | 0.5325 | 0.033* | |
C6 | 0.89443 (10) | 0.5470 (2) | 0.58242 (5) | 0.0204 (2) | |
C7 | 0.90903 (11) | 0.4571 (2) | 0.70494 (5) | 0.0202 (2) | |
H7A | 0.9579 | 0.4299 | 0.7451 | 0.024* | |
H7B | 0.8549 | 0.6026 | 0.7104 | 0.024* | |
C8 | 0.83135 (10) | 0.2310 (2) | 0.68959 (5) | 0.0191 (2) | |
C9 | 0.68427 (11) | 0.0192 (2) | 0.61862 (6) | 0.0206 (2) | |
H9A | 0.7166 | −0.1296 | 0.6415 | 0.025* | |
H9B | 0.6814 | −0.0193 | 0.5729 | 0.025* | |
C10 | 0.55414 (10) | 0.0666 (2) | 0.63773 (5) | 0.0185 (2) | |
C11 | 0.52211 (11) | 0.2662 (2) | 0.67490 (5) | 0.0239 (3) | |
H11 | 0.5828 | 0.3854 | 0.6879 | 0.029* | |
C12 | 0.40231 (12) | 0.2935 (3) | 0.69330 (5) | 0.0290 (3) | |
H12 | 0.3813 | 0.4312 | 0.7186 | 0.035* | |
C13 | 0.31340 (12) | 0.1201 (3) | 0.67478 (6) | 0.0302 (3) | |
H13 | 0.2314 | 0.1387 | 0.6874 | 0.036* | |
C14 | 0.34421 (12) | −0.0800 (3) | 0.63797 (7) | 0.0319 (3) | |
H14 | 0.2835 | −0.1998 | 0.6255 | 0.038* | |
C15 | 0.46353 (11) | −0.1061 (2) | 0.61924 (6) | 0.0261 (3) | |
H15 | 0.4839 | −0.2430 | 0.5935 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01580 (17) | 0.0344 (2) | 0.02528 (17) | −0.00305 (11) | −0.00034 (12) | 0.00452 (11) |
O1 | 0.0243 (4) | 0.0259 (5) | 0.0282 (4) | −0.0015 (4) | −0.0014 (3) | 0.0087 (3) |
N1 | 0.0177 (4) | 0.0169 (5) | 0.0215 (4) | −0.0014 (4) | −0.0006 (3) | −0.0006 (3) |
C1 | 0.0192 (5) | 0.0181 (5) | 0.0178 (5) | 0.0024 (4) | 0.0019 (4) | −0.0025 (4) |
C2 | 0.0227 (6) | 0.0244 (6) | 0.0210 (5) | −0.0001 (5) | −0.0022 (4) | −0.0040 (4) |
C3 | 0.0296 (6) | 0.0309 (7) | 0.0189 (5) | 0.0040 (5) | −0.0033 (5) | −0.0025 (5) |
C4 | 0.0343 (7) | 0.0302 (7) | 0.0209 (5) | 0.0020 (5) | 0.0051 (5) | 0.0054 (5) |
C5 | 0.0243 (6) | 0.0318 (7) | 0.0263 (6) | −0.0026 (5) | 0.0060 (5) | 0.0039 (5) |
C6 | 0.0171 (5) | 0.0245 (6) | 0.0198 (5) | 0.0022 (4) | 0.0019 (4) | −0.0011 (4) |
C7 | 0.0200 (5) | 0.0219 (6) | 0.0186 (5) | −0.0010 (4) | −0.0006 (4) | 0.0009 (4) |
C8 | 0.0157 (5) | 0.0195 (6) | 0.0220 (5) | 0.0034 (4) | 0.0011 (4) | 0.0006 (4) |
C9 | 0.0195 (6) | 0.0145 (5) | 0.0276 (6) | −0.0002 (4) | 0.0003 (4) | −0.0032 (4) |
C10 | 0.0187 (5) | 0.0167 (5) | 0.0200 (5) | 0.0008 (4) | −0.0010 (4) | 0.0021 (4) |
C11 | 0.0239 (6) | 0.0234 (6) | 0.0242 (5) | 0.0017 (5) | −0.0014 (4) | −0.0022 (4) |
C12 | 0.0302 (7) | 0.0345 (7) | 0.0228 (5) | 0.0097 (6) | 0.0050 (5) | −0.0008 (5) |
C13 | 0.0218 (6) | 0.0410 (8) | 0.0283 (6) | 0.0048 (5) | 0.0055 (5) | 0.0115 (6) |
C14 | 0.0218 (6) | 0.0306 (7) | 0.0430 (7) | −0.0051 (5) | −0.0014 (5) | 0.0061 (6) |
C15 | 0.0236 (6) | 0.0196 (6) | 0.0349 (6) | −0.0012 (5) | −0.0004 (5) | −0.0023 (5) |
S1—C6 | 1.7583 (11) | C7—H7A | 0.9900 |
S1—C7 | 1.8013 (12) | C7—H7B | 0.9900 |
O1—C8 | 1.2262 (14) | C9—C10 | 1.5144 (16) |
N1—C8 | 1.3781 (13) | C9—H9A | 0.9900 |
N1—C1 | 1.4191 (14) | C9—H9B | 0.9900 |
N1—C9 | 1.4628 (14) | C10—C11 | 1.3880 (16) |
C1—C6 | 1.4012 (16) | C10—C15 | 1.3947 (16) |
C1—C2 | 1.4047 (15) | C11—C12 | 1.3876 (17) |
C2—C3 | 1.3860 (18) | C11—H11 | 0.9500 |
C2—H2 | 0.9500 | C12—C13 | 1.3848 (19) |
C3—C4 | 1.3859 (19) | C12—H12 | 0.9500 |
C3—H3 | 0.9500 | C13—C14 | 1.382 (2) |
C4—C5 | 1.3833 (16) | C13—H13 | 0.9500 |
C4—H4 | 0.9500 | C14—C15 | 1.3843 (18) |
C5—C6 | 1.3940 (17) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C7—C8 | 1.5066 (16) | ||
C6—S1—C7 | 95.66 (5) | O1—C8—N1 | 121.21 (10) |
C8—N1—C1 | 123.74 (9) | O1—C8—C7 | 121.93 (10) |
C8—N1—C9 | 116.79 (9) | N1—C8—C7 | 116.84 (9) |
C1—N1—C9 | 119.46 (9) | N1—C9—C10 | 115.07 (9) |
C6—C1—C2 | 118.72 (10) | N1—C9—H9A | 108.5 |
C6—C1—N1 | 121.15 (9) | C10—C9—H9A | 108.5 |
C2—C1—N1 | 120.07 (10) | N1—C9—H9B | 108.5 |
C3—C2—C1 | 120.60 (11) | C10—C9—H9B | 108.5 |
C3—C2—H2 | 119.7 | H9A—C9—H9B | 107.5 |
C1—C2—H2 | 119.7 | C11—C10—C15 | 118.70 (11) |
C4—C3—C2 | 120.38 (11) | C11—C10—C9 | 123.32 (10) |
C4—C3—H3 | 119.8 | C15—C10—C9 | 117.92 (10) |
C2—C3—H3 | 119.8 | C12—C11—C10 | 120.65 (12) |
C5—C4—C3 | 119.52 (11) | C12—C11—H11 | 119.7 |
C5—C4—H4 | 120.2 | C10—C11—H11 | 119.7 |
C3—C4—H4 | 120.2 | C13—C12—C11 | 120.02 (12) |
C4—C5—C6 | 121.00 (12) | C13—C12—H12 | 120.0 |
C4—C5—H5 | 119.5 | C11—C12—H12 | 120.0 |
C6—C5—H5 | 119.5 | C14—C13—C12 | 119.89 (12) |
C5—C6—C1 | 119.76 (10) | C14—C13—H13 | 120.1 |
C5—C6—S1 | 119.15 (9) | C12—C13—H13 | 120.1 |
C1—C6—S1 | 121.08 (9) | C13—C14—C15 | 120.04 (12) |
C8—C7—S1 | 110.56 (8) | C13—C14—H14 | 120.0 |
C8—C7—H7A | 109.5 | C15—C14—H14 | 120.0 |
S1—C7—H7A | 109.5 | C14—C15—C10 | 120.69 (12) |
C8—C7—H7B | 109.5 | C14—C15—H15 | 119.7 |
S1—C7—H7B | 109.5 | C10—C15—H15 | 119.7 |
H7A—C7—H7B | 108.1 | ||
C8—N1—C1—C6 | 23.43 (16) | C1—N1—C8—O1 | −175.23 (10) |
C9—N1—C1—C6 | −156.89 (11) | C9—N1—C8—O1 | 5.09 (15) |
C8—N1—C1—C2 | −159.32 (11) | C1—N1—C8—C7 | 6.40 (15) |
C9—N1—C1—C2 | 20.36 (15) | C9—N1—C8—C7 | −173.29 (10) |
C6—C1—C2—C3 | 1.99 (17) | S1—C7—C8—O1 | 131.04 (10) |
N1—C1—C2—C3 | −175.32 (11) | S1—C7—C8—N1 | −50.60 (12) |
C1—C2—C3—C4 | −0.93 (19) | C8—N1—C9—C10 | 88.08 (12) |
C2—C3—C4—C5 | −0.81 (19) | C1—N1—C9—C10 | −91.62 (12) |
C3—C4—C5—C6 | 1.48 (19) | N1—C9—C10—C11 | −12.01 (16) |
C4—C5—C6—C1 | −0.40 (19) | N1—C9—C10—C15 | 170.98 (10) |
C4—C5—C6—S1 | 178.35 (10) | C15—C10—C11—C12 | 0.00 (17) |
C2—C1—C6—C5 | −1.33 (17) | C9—C10—C11—C12 | −176.99 (11) |
N1—C1—C6—C5 | 175.96 (11) | C10—C11—C12—C13 | 0.24 (18) |
C2—C1—C6—S1 | 179.95 (9) | C11—C12—C13—C14 | 0.01 (18) |
N1—C1—C6—S1 | −2.77 (15) | C12—C13—C14—C15 | −0.51 (19) |
C7—S1—C6—C5 | 147.46 (11) | C13—C14—C15—C10 | 0.75 (19) |
C7—S1—C6—C1 | −33.80 (10) | C11—C10—C15—C14 | −0.49 (18) |
C6—S1—C7—C8 | 57.87 (9) | C9—C10—C15—C14 | 176.66 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O1i | 0.99 | 2.55 | 3.2504 (14) | 128 |
C7—H7B···O1ii | 0.99 | 2.53 | 3.4403 (15) | 152 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O1i | 0.99 | 2.55 | 3.2504 (14) | 128 |
C7—H7B···O1ii | 0.99 | 2.53 | 3.4403 (15) | 152 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z. |
As a continuation of our research devoted to the development of substituted 1,4-benzothiazine derivatives (Zerzouf et al., 2001; Sebbar et al., 2015), we report the synthesis of a 1,4-benzothiazine derivative by reaction of benzyl chloride with 2H-benzo[b][1,4]thiazin-3(4H)-one in the presence of tetra-n-butylammonium bromide as catalyst and potassium carbonate as base (Scheme 1).
In the title compound, the heterocyclic ring has puckering parameters Q = 0.6272 (10) Å, θ = 63.91 (10)° and φ = 325.56 (11)°. The dihedral angle between the rings C1-C6 and C10-C15 is 86.54 (4)°. Weak C—H···O interactions (Table 1) form chains running parallel to the b axis (Fig. 2).