Crystal structure of (Z)-ethyl 2-{5-[(2-benzyl-idene-3-oxo-2,3-di-hydro-benzo[b][1,4]thia-zin-4-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

The title compound, C22H20N4O3S, features two fused six-membered rings linked to a 1,2,3-triazole ring which is attached to an ethyl acetate group. The heterocycle in the benzo-thia-zine residue has an envelope conformation with the S atom being the flap. The conformation of the ethyl acetate side chain, which is directed to the same side of the mol-ecule as the C6 ring of the fused-ring system, may be partially established by a pair of weak intra-molecular C-H⋯O(carbon-yl) inter-actions. The three-dimensional packing is aided by inter-molecular C-H⋯O and C-H⋯N inter-actions.

Related literature

For the biological activity of 1,4-benzo­thia­zine derivatives, see: Goyal et al. (2013 ▸); Gupta et al. (2011 ▸); Gautam et al. (2013 ▸); Deshmukh & Mulik (2004 ▸); Kumar et al. (2010 ▸); Hans et al. (2008 ▸); Gao et al. (2005 ▸); Bakavoli et al. (2007 ▸). For applications of 1,4-benzo­thia­zine derivatives, see: Podsiadły et al. (2009 ▸); Hong et al. (2008 ▸). For structures of 1,4-benzo­thia­zine derivatives, see: Sebbar et al. (2014 ▸).

Experimental

Crystal data

C22H20N4O3S

M = 420.48

Monoclinic,

a = 9.9767 (6) Å

b = 8.7342 (5) Å

c = 23.1027 (14) Å

β = 94.508 (1)°

V = 2006.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 150 K

0.32 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2015 ▸) T min = 0.86, T max = 0.95

37542 measured reflections

5341 independent reflections

4380 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.04

5341 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2015 ▸); cell refinement: SAINT (Bruker, 2015 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015022987/tk5410sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022987/tk5410Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022987/tk5410Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015022987/tk5410fig1.tif

The title mol­ecule showing the labeling scheme and 50% probability ellipsoids. Intra­molecular C—H⋯O inter­actions are shown by dotted lines.

Click here for additional data file.

b . DOI: 10.1107/S2056989015022987/tk5410fig2.tif

Packing viewed down the b axis. Inter­molecular C—H⋯O inter­actions are shown by dotted lines.

CCDC reference: 1439697

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H20N4O3S	F(000) = 880
Mr = 420.48	Dx = 1.392 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.9767 (6) Å	Cell parameters from 9992 reflections
b = 8.7342 (5) Å	θ = 2.2–29.0°
c = 23.1027 (14) Å	µ = 0.19 mm−1
β = 94.508 (1)°	T = 150 K
V = 2006.9 (2) Å3	Block, colourless
Z = 4	0.32 × 0.28 × 0.25 mm

Bruker SMART APEX CCD diffractometer	5341 independent reflections
Radiation source: fine-focus sealed tube	4380 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.3333 pixels mm-1	θmax = 29.1°, θmin = 1.8°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −11→11
Tmin = 0.86, Tmax = 0.95	l = −30→31
37542 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.6062P] where P = (Fo2 + 2Fc2)/3
5341 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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 8 sec/frame.

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. 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 − 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
S1	0.06354 (3)	0.15135 (4)	0.40087 (2)	0.02889 (10)
O1	0.31909 (10)	0.34881 (14)	0.51171 (4)	0.0355 (3)
O2	0.61888 (11)	0.57371 (14)	0.32065 (5)	0.0404 (3)
O3	0.83615 (10)	0.63206 (12)	0.34309 (5)	0.0307 (2)
N1	0.31595 (11)	0.34444 (14)	0.41352 (5)	0.0262 (2)
N2	0.66451 (10)	0.28821 (13)	0.37357 (5)	0.0243 (2)
N3	0.70889 (12)	0.16441 (15)	0.34542 (6)	0.0326 (3)
N4	0.60856 (13)	0.06776 (15)	0.33911 (6)	0.0374 (3)
C1	0.24452 (13)	0.34916 (16)	0.35742 (6)	0.0254 (3)
C2	0.29275 (14)	0.43188 (18)	0.31212 (7)	0.0322 (3)
H2	0.3737	0.4888	0.3184	0.039*
C3	0.22313 (15)	0.4319 (2)	0.25761 (7)	0.0364 (3)
H3	0.2568	0.4895	0.2270	0.044*
C4	0.10540 (15)	0.34906 (19)	0.24722 (7)	0.0350 (3)
H4	0.0590	0.3489	0.2097	0.042*
C5	0.05591 (14)	0.26665 (17)	0.29200 (6)	0.0296 (3)
H5	−0.0256	0.2108	0.2854	0.036*
C6	0.12545 (13)	0.26549 (16)	0.34678 (6)	0.0250 (3)
C7	0.11667 (13)	0.26130 (16)	0.46180 (6)	0.0256 (3)
C8	0.25729 (13)	0.32240 (17)	0.46472 (6)	0.0265 (3)
C9	0.04663 (13)	0.27766 (16)	0.50890 (6)	0.0275 (3)
H9	0.0936	0.3301	0.5403	0.033*
C10	−0.08942 (13)	0.22868 (16)	0.52021 (6)	0.0274 (3)
C11	−0.16582 (15)	0.11893 (19)	0.48788 (7)	0.0333 (3)
H11	−0.1284	0.0672	0.4568	0.040*
C12	−0.29624 (16)	0.0855 (2)	0.50125 (8)	0.0413 (4)
H12	−0.3479	0.0126	0.4786	0.050*
C13	−0.35135 (16)	0.1574 (2)	0.54703 (9)	0.0442 (4)
H13	−0.4413	0.1359	0.5552	0.053*
C14	−0.27500 (16)	0.2608 (2)	0.58095 (8)	0.0422 (4)
H14	−0.3113	0.3075	0.6134	0.051*
C15	−0.14533 (15)	0.29617 (18)	0.56757 (7)	0.0342 (3)
H15	−0.0938	0.3675	0.5910	0.041*
C16	0.45934 (12)	0.38457 (18)	0.41794 (6)	0.0279 (3)
H16A	0.4944	0.3859	0.4592	0.033*
H16B	0.4714	0.4879	0.4016	0.033*
C17	0.53491 (12)	0.27008 (16)	0.38550 (6)	0.0247 (3)
C18	0.50109 (14)	0.12925 (17)	0.36318 (7)	0.0309 (3)
H18	0.4157	0.0818	0.3643	0.037*
C19	0.75516 (12)	0.41430 (16)	0.38687 (6)	0.0263 (3)
H19A	0.8488	0.3793	0.3842	0.032*
H19B	0.7462	0.4486	0.4272	0.032*
C20	0.72677 (13)	0.54792 (17)	0.34581 (6)	0.0271 (3)
C21	0.82319 (18)	0.7661 (2)	0.30459 (8)	0.0434 (4)
H21A	0.7736	0.8489	0.3229	0.052*
H21B	0.7735	0.7384	0.2673	0.052*
C22	0.96129 (19)	0.8177 (2)	0.29460 (9)	0.0494 (5)
H22A	1.0087	0.8471	0.3317	0.074*
H22B	0.9564	0.9059	0.2683	0.074*
H22C	1.0100	0.7341	0.2772	0.074*

	U11	U22	U33	U12	U13	U23
S1	0.02741 (17)	0.03138 (19)	0.02719 (18)	−0.00666 (13)	−0.00227 (13)	−0.00326 (13)
O1	0.0253 (5)	0.0528 (7)	0.0275 (5)	−0.0067 (4)	−0.0030 (4)	−0.0082 (5)
O2	0.0279 (5)	0.0415 (6)	0.0497 (7)	−0.0022 (5)	−0.0106 (5)	0.0113 (5)
O3	0.0245 (5)	0.0307 (5)	0.0366 (6)	−0.0035 (4)	−0.0004 (4)	0.0053 (4)
N1	0.0167 (5)	0.0345 (6)	0.0269 (6)	−0.0013 (4)	−0.0020 (4)	−0.0043 (5)
N2	0.0179 (5)	0.0254 (6)	0.0289 (6)	0.0010 (4)	−0.0023 (4)	−0.0022 (4)
N3	0.0252 (6)	0.0314 (7)	0.0405 (7)	0.0047 (5)	−0.0021 (5)	−0.0087 (5)
N4	0.0284 (6)	0.0304 (7)	0.0517 (8)	0.0027 (5)	−0.0068 (5)	−0.0102 (6)
C1	0.0198 (6)	0.0292 (7)	0.0266 (7)	0.0027 (5)	−0.0019 (5)	−0.0027 (5)
C2	0.0248 (6)	0.0369 (8)	0.0344 (8)	−0.0022 (6)	−0.0003 (5)	0.0014 (6)
C3	0.0326 (7)	0.0433 (9)	0.0329 (8)	0.0008 (6)	0.0004 (6)	0.0087 (7)
C4	0.0315 (7)	0.0422 (9)	0.0297 (7)	0.0049 (6)	−0.0073 (6)	0.0038 (6)
C5	0.0222 (6)	0.0347 (8)	0.0306 (7)	0.0019 (5)	−0.0061 (5)	−0.0015 (6)
C6	0.0207 (6)	0.0273 (7)	0.0265 (6)	0.0024 (5)	−0.0012 (5)	−0.0017 (5)
C7	0.0213 (6)	0.0274 (7)	0.0274 (7)	−0.0009 (5)	−0.0032 (5)	−0.0022 (5)
C8	0.0203 (6)	0.0303 (7)	0.0284 (7)	−0.0002 (5)	−0.0008 (5)	−0.0044 (5)
C9	0.0230 (6)	0.0291 (7)	0.0297 (7)	−0.0036 (5)	−0.0018 (5)	−0.0012 (5)
C10	0.0221 (6)	0.0297 (7)	0.0299 (7)	−0.0011 (5)	−0.0016 (5)	0.0068 (6)
C11	0.0312 (7)	0.0376 (8)	0.0303 (7)	−0.0079 (6)	−0.0035 (6)	0.0063 (6)
C12	0.0308 (7)	0.0465 (9)	0.0444 (9)	−0.0142 (7)	−0.0114 (7)	0.0170 (8)
C13	0.0229 (7)	0.0488 (10)	0.0605 (11)	−0.0008 (6)	0.0014 (7)	0.0215 (9)
C14	0.0324 (8)	0.0389 (9)	0.0570 (11)	0.0046 (7)	0.0144 (7)	0.0082 (8)
C15	0.0299 (7)	0.0309 (8)	0.0421 (8)	0.0006 (6)	0.0055 (6)	0.0022 (6)
C16	0.0170 (6)	0.0350 (7)	0.0312 (7)	−0.0032 (5)	−0.0006 (5)	−0.0067 (6)
C17	0.0182 (6)	0.0285 (7)	0.0266 (6)	−0.0005 (5)	−0.0032 (5)	0.0002 (5)
C18	0.0238 (6)	0.0287 (7)	0.0389 (8)	−0.0019 (5)	−0.0052 (6)	−0.0025 (6)
C19	0.0175 (5)	0.0292 (7)	0.0315 (7)	−0.0022 (5)	−0.0033 (5)	0.0003 (5)
C20	0.0238 (6)	0.0290 (7)	0.0280 (7)	−0.0003 (5)	−0.0004 (5)	−0.0022 (5)
C21	0.0411 (9)	0.0374 (9)	0.0515 (10)	−0.0001 (7)	0.0013 (7)	0.0147 (8)
C22	0.0488 (10)	0.0489 (10)	0.0496 (10)	−0.0152 (8)	−0.0022 (8)	0.0153 (9)

S1—C6	1.7488 (15)	C9—H9	0.9500
S1—C7	1.7513 (14)	C10—C15	1.397 (2)
O1—C8	1.2275 (16)	C10—C11	1.403 (2)
O2—C20	1.2037 (16)	C11—C12	1.392 (2)
O3—C20	1.3212 (16)	C11—H11	0.9500
O3—C21	1.4696 (19)	C12—C13	1.380 (3)
N1—C8	1.3738 (18)	C12—H12	0.9500
N1—C1	1.4297 (17)	C13—C14	1.384 (3)
N1—C16	1.4686 (16)	C13—H13	0.9500
N2—C17	1.3523 (16)	C14—C15	1.388 (2)
N2—N3	1.3540 (17)	C14—H14	0.9500
N2—C19	1.4427 (17)	C15—H15	0.9500
N3—N4	1.3088 (18)	C16—C17	1.4897 (19)
N4—C18	1.357 (2)	C16—H16A	0.9900
C1—C2	1.389 (2)	C16—H16B	0.9900
C1—C6	1.3999 (18)	C17—C18	1.366 (2)
C2—C3	1.390 (2)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.516 (2)
C3—C4	1.384 (2)	C19—H19A	0.9900
C3—H3	0.9500	C19—H19B	0.9900
C4—C5	1.383 (2)	C21—C22	1.485 (2)
C4—H4	0.9500	C21—H21A	0.9900
C5—C6	1.3946 (18)	C21—H21B	0.9900
C5—H5	0.9500	C22—H22A	0.9800
C7—C9	1.346 (2)	C22—H22B	0.9800
C7—C8	1.4975 (18)	C22—H22C	0.9800
C9—C10	1.4660 (19)
C6—S1—C7	99.22 (7)	C13—C12—H12	119.7
C20—O3—C21	115.99 (11)	C11—C12—H12	119.7
C8—N1—C1	124.67 (11)	C12—C13—C14	119.71 (15)
C8—N1—C16	116.88 (11)	C12—C13—H13	120.1
C1—N1—C16	118.01 (11)	C14—C13—H13	120.1
C17—N2—N3	111.00 (11)	C13—C14—C15	120.01 (17)
C17—N2—C19	129.74 (12)	C13—C14—H14	120.0
N3—N2—C19	119.26 (11)	C15—C14—H14	120.0
N4—N3—N2	107.01 (11)	C14—C15—C10	121.12 (16)
N3—N4—C18	108.73 (12)	C14—C15—H15	119.4
C2—C1—C6	118.60 (13)	C10—C15—H15	119.4
C2—C1—N1	121.38 (12)	N1—C16—C17	109.49 (11)
C6—C1—N1	119.99 (12)	N1—C16—H16A	109.8
C1—C2—C3	120.32 (14)	C17—C16—H16A	109.8
C1—C2—H2	119.8	N1—C16—H16B	109.8
C3—C2—H2	119.8	C17—C16—H16B	109.8
C4—C3—C2	120.94 (15)	H16A—C16—H16B	108.2
C4—C3—H3	119.5	N2—C17—C18	103.91 (12)
C2—C3—H3	119.5	N2—C17—C16	123.63 (12)
C5—C4—C3	119.36 (14)	C18—C17—C16	132.43 (12)
C5—C4—H4	120.3	N4—C18—C17	109.36 (13)
C3—C4—H4	120.3	N4—C18—H18	125.3
C4—C5—C6	120.08 (13)	C17—C18—H18	125.3
C4—C5—H5	120.0	N2—C19—C20	111.79 (11)
C6—C5—H5	120.0	N2—C19—H19A	109.3
C5—C6—C1	120.69 (13)	C20—C19—H19A	109.3
C5—C6—S1	118.30 (11)	N2—C19—H19B	109.3
C1—C6—S1	120.97 (10)	C20—C19—H19B	109.3
C9—C7—C8	118.01 (12)	H19A—C19—H19B	107.9
C9—C7—S1	124.36 (10)	O2—C20—O3	125.70 (14)
C8—C7—S1	117.06 (10)	O2—C20—C19	124.20 (13)
O1—C8—N1	121.12 (12)	O3—C20—C19	110.09 (11)
O1—C8—C7	120.70 (13)	O3—C21—C22	107.30 (14)
N1—C8—C7	118.17 (11)	O3—C21—H21A	110.3
C7—C9—C10	131.28 (13)	C22—C21—H21A	110.3
C7—C9—H9	114.4	O3—C21—H21B	110.3
C10—C9—H9	114.4	C22—C21—H21B	110.3
C15—C10—C11	118.13 (13)	H21A—C21—H21B	108.5
C15—C10—C9	116.66 (13)	C21—C22—H22A	109.5
C11—C10—C9	125.20 (14)	C21—C22—H22B	109.5
C12—C11—C10	120.22 (16)	H22A—C22—H22B	109.5
C12—C11—H11	119.9	C21—C22—H22C	109.5
C10—C11—H11	119.9	H22A—C22—H22C	109.5
C13—C12—C11	120.69 (16)	H22B—C22—H22C	109.5
C17—N2—N3—N4	0.23 (16)	C8—C7—C9—C10	−178.60 (14)
C19—N2—N3—N4	179.65 (12)	S1—C7—C9—C10	−7.6 (2)
N2—N3—N4—C18	−0.15 (17)	C7—C9—C10—C15	−164.25 (15)
C8—N1—C1—C2	152.35 (14)	C7—C9—C10—C11	16.7 (3)
C16—N1—C1—C2	−19.71 (19)	C15—C10—C11—C12	3.4 (2)
C8—N1—C1—C6	−29.6 (2)	C9—C10—C11—C12	−177.55 (14)
C16—N1—C1—C6	158.31 (13)	C10—C11—C12—C13	−1.3 (2)
C6—C1—C2—C3	0.5 (2)	C11—C12—C13—C14	−1.7 (2)
N1—C1—C2—C3	178.50 (14)	C12—C13—C14—C15	2.4 (3)
C1—C2—C3—C4	−0.4 (2)	C13—C14—C15—C10	−0.2 (3)
C2—C3—C4—C5	0.7 (2)	C11—C10—C15—C14	−2.7 (2)
C3—C4—C5—C6	−1.0 (2)	C9—C10—C15—C14	178.17 (14)
C4—C5—C6—C1	1.0 (2)	C8—N1—C16—C17	122.76 (13)
C4—C5—C6—S1	−176.62 (12)	C1—N1—C16—C17	−64.56 (16)
C2—C1—C6—C5	−0.7 (2)	N3—N2—C17—C18	−0.20 (15)
N1—C1—C6—C5	−178.82 (13)	C19—N2—C17—C18	−179.55 (13)
C2—C1—C6—S1	176.83 (11)	N3—N2—C17—C16	177.86 (13)
N1—C1—C6—S1	−1.25 (18)	C19—N2—C17—C16	−1.5 (2)
C7—S1—C6—C5	−149.26 (11)	N1—C16—C17—N2	169.08 (12)
C7—S1—C6—C1	33.12 (13)	N1—C16—C17—C18	−13.5 (2)
C6—S1—C7—C9	144.28 (13)	N3—N4—C18—C17	0.03 (18)
C6—S1—C7—C8	−44.59 (12)	N2—C17—C18—N4	0.11 (16)
C1—N1—C8—O1	−165.70 (14)	C16—C17—C18—N4	−177.71 (15)
C16—N1—C8—O1	6.4 (2)	C17—N2—C19—C20	−77.52 (18)
C1—N1—C8—C7	15.8 (2)	N3—N2—C19—C20	103.18 (14)
C16—N1—C8—C7	−172.03 (12)	C21—O3—C20—O2	−1.6 (2)
C9—C7—C8—O1	18.9 (2)	C21—O3—C20—C19	179.90 (13)
S1—C7—C8—O1	−152.77 (12)	N2—C19—C20—O2	26.0 (2)
C9—C7—C8—N1	−162.59 (13)	N2—C19—C20—O3	−155.45 (12)
S1—C7—C8—N1	25.70 (17)	C20—O3—C21—C22	−164.23 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.95	2.55	3.4726 (18)	163
C16—H16B···O2	0.99	2.58	3.2981 (19)	129
C19—H19B···O1i	0.99	2.39	3.2547 (18)	146
C21—H21A···N4ii	0.99	2.57	3.526 (2)	162
C22—H22B···O2iii	0.98	2.59	3.521 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.95	2.55	3.4726 (18)	163
C16—H16B⋯O2	0.99	2.58	3.2981 (19)	129
C19—H19B⋯O1i	0.99	2.39	3.2547 (18)	146
C21—H21A⋯N4ii	0.99	2.57	3.526 (2)	162
C22—H22B⋯O2iii	0.98	2.59	3.521 (2)	159

Symmetry codes: (i) ; (ii) ; (iii) .