Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(2,4-di­chloro­benzyl­idene)-4-[2-(2-oxo-1,3-oxazolidin-3-yl)eth­yl]-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one

In the title compound, the heterocyclic portion of the di­hydro­benzo­thia­zine unit adopts a flattened-boat conformation, while the oxazolidine ring adopts an envelope conformation. The 2-carbon link to the oxazole ring is perpendicular to the best plane through the di­hydro­benzo­thia­zine unit. In the crystal, the mol­ecules form stacks extending along the normal to (104) through π-stacking inter­actions between the two carbonyl groups and inversion-related oxazole rings. Aromatic rings from neighbouring stacks inter­calate to form an overall layer structure.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.093
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         16 Report

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             109.4 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   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
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   2 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(2Z)-2-(2,4-Dichlorobenzylidene)-4-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-3,4-dihydro-2H-1,4-benzothiazin-3-one

Crystal data

C20H16Cl2N2O3S	F(000) = 896
Mr = 435.31	Dx = 1.548 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 18.4615 (8) Å	Cell parameters from 9952 reflections
b = 12.8567 (5) Å	θ = 3.5–72.5°
c = 7.9251 (4) Å	µ = 4.39 mm^−1
β = 96.926 (2)°	T = 150 K
V = 1867.33 (14) Å^3	Column, light yellow
Z = 4	0.21 × 0.12 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3678 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3252 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.5°, θmin = 2.4°
ω scans	h = −22→21
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −14→15
Tmin = 0.51, Tmax = 0.80	l = −9→9
14033 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: difference Fourier map
wR(F^2) = 0.093	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.9972P] where P = (Fo^2 + 2Fc^2)/3
3678 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−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
Cl1	−0.02396 (3)	0.92135 (4)	0.75404 (8)	0.05021 (17)
Cl2	0.23463 (3)	0.91630 (3)	0.51698 (8)	0.04067 (15)
S1	0.17782 (2)	0.48226 (3)	0.53284 (7)	0.03232 (14)
O1	0.35726 (7)	0.62658 (10)	0.44041 (18)	0.0330 (3)
O2	0.61496 (6)	0.46053 (10)	0.16700 (16)	0.0267 (3)
O3	0.54282 (7)	0.59880 (10)	0.19909 (16)	0.0299 (3)
N1	0.33467 (7)	0.45458 (11)	0.42952 (18)	0.0227 (3)
N2	0.49920 (8)	0.43048 (11)	0.19710 (19)	0.0240 (3)
C1	0.21852 (9)	0.36941 (13)	0.4668 (2)	0.0237 (3)
C2	0.17612 (10)	0.27967 (14)	0.4671 (3)	0.0298 (4)
H2	0.1287 (13)	0.2873 (18)	0.496 (3)	0.036 (6)*
C3	0.20375 (10)	0.18467 (15)	0.4260 (3)	0.0328 (4)
H3	0.1739 (14)	0.125 (2)	0.424 (3)	0.043 (6)*
C4	0.27384 (10)	0.17928 (14)	0.3800 (2)	0.0299 (4)
H4	0.2935 (12)	0.1146 (19)	0.352 (3)	0.037 (6)*
C5	0.31603 (10)	0.26806 (14)	0.3770 (2)	0.0255 (4)
H5	0.3619 (13)	0.2616 (18)	0.342 (3)	0.035 (6)*
C6	0.28970 (9)	0.36498 (13)	0.4241 (2)	0.0221 (3)
C7	0.31385 (9)	0.55557 (13)	0.4532 (2)	0.0238 (3)
C8	0.23937 (9)	0.57999 (13)	0.5014 (2)	0.0233 (3)
C9	0.41197 (9)	0.44207 (14)	0.4043 (2)	0.0235 (3)
H9A	0.4306 (11)	0.3741 (17)	0.457 (3)	0.029 (5)*
H9B	0.4388 (11)	0.4975 (17)	0.468 (3)	0.028 (5)*
C10	0.42367 (9)	0.45187 (15)	0.2187 (2)	0.0264 (4)
H10A	0.3897 (12)	0.4031 (17)	0.146 (3)	0.031 (5)*
H10B	0.4108 (12)	0.5235 (18)	0.181 (3)	0.033 (6)*
C11	0.52850 (10)	0.32643 (14)	0.1876 (3)	0.0285 (4)
H11A	0.4991 (13)	0.2859 (18)	0.099 (3)	0.038 (6)*
H11B	0.5292 (13)	0.2906 (19)	0.295 (3)	0.043 (6)*
C12	0.60490 (10)	0.34916 (14)	0.1433 (2)	0.0272 (4)
H12A	0.6082 (12)	0.3331 (18)	0.024 (3)	0.037 (6)*
H12B	0.6420 (13)	0.3167 (19)	0.219 (3)	0.039 (6)*
C13	0.54980 (9)	0.50543 (13)	0.1887 (2)	0.0227 (3)
C14	0.22602 (9)	0.68205 (14)	0.5250 (2)	0.0246 (4)
H14	0.2654 (11)	0.7266 (17)	0.504 (3)	0.027 (5)*
C15	0.16331 (9)	0.73590 (13)	0.5785 (2)	0.0241 (4)
C16	0.10234 (10)	0.68752 (15)	0.6352 (3)	0.0311 (4)
H16	0.0973 (13)	0.612 (2)	0.640 (3)	0.044 (7)*
C17	0.04455 (10)	0.74288 (16)	0.6871 (3)	0.0344 (4)
H17	0.0037 (15)	0.710 (2)	0.725 (3)	0.050 (7)*
C18	0.04662 (10)	0.84994 (16)	0.6841 (3)	0.0330 (4)
C19	0.10510 (10)	0.90291 (15)	0.6301 (3)	0.0325 (4)
H19	0.1073 (11)	0.9771 (19)	0.626 (3)	0.032 (6)*
C20	0.16222 (10)	0.84560 (14)	0.5794 (2)	0.0271 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0335 (3)	0.0432 (3)	0.0774 (4)	0.0150 (2)	0.0207 (3)	−0.0079 (3)
Cl2	0.0354 (3)	0.0187 (2)	0.0718 (4)	−0.00040 (17)	0.0224 (2)	0.0036 (2)
S1	0.0250 (2)	0.0169 (2)	0.0593 (3)	−0.00047 (16)	0.0225 (2)	−0.00057 (19)
O1	0.0279 (6)	0.0224 (7)	0.0522 (8)	−0.0045 (5)	0.0198 (6)	−0.0021 (6)
O2	0.0227 (6)	0.0208 (6)	0.0390 (7)	−0.0020 (5)	0.0131 (5)	−0.0006 (5)
O3	0.0380 (7)	0.0183 (6)	0.0349 (7)	0.0008 (5)	0.0106 (5)	0.0001 (5)
N1	0.0187 (7)	0.0201 (7)	0.0308 (7)	0.0006 (5)	0.0097 (5)	−0.0007 (6)
N2	0.0224 (7)	0.0182 (7)	0.0338 (8)	−0.0002 (5)	0.0131 (6)	−0.0008 (6)
C1	0.0231 (8)	0.0175 (8)	0.0316 (9)	0.0011 (6)	0.0080 (7)	0.0013 (6)
C2	0.0232 (8)	0.0219 (9)	0.0454 (11)	−0.0026 (7)	0.0097 (7)	0.0003 (8)
C3	0.0306 (9)	0.0192 (9)	0.0493 (12)	−0.0039 (7)	0.0079 (8)	−0.0017 (8)
C4	0.0323 (9)	0.0187 (9)	0.0395 (10)	0.0027 (7)	0.0070 (8)	−0.0039 (7)
C5	0.0252 (8)	0.0221 (9)	0.0304 (9)	0.0036 (7)	0.0083 (7)	−0.0007 (7)
C6	0.0220 (8)	0.0183 (8)	0.0268 (8)	−0.0015 (6)	0.0060 (6)	0.0008 (6)
C7	0.0225 (8)	0.0186 (8)	0.0320 (9)	−0.0007 (6)	0.0105 (7)	0.0000 (7)
C8	0.0212 (8)	0.0187 (8)	0.0319 (9)	−0.0005 (6)	0.0103 (6)	0.0012 (6)
C9	0.0167 (7)	0.0272 (9)	0.0274 (8)	0.0014 (7)	0.0063 (6)	−0.0011 (7)
C10	0.0219 (8)	0.0298 (10)	0.0287 (9)	0.0022 (7)	0.0079 (7)	0.0010 (7)
C11	0.0294 (9)	0.0171 (8)	0.0412 (10)	−0.0003 (7)	0.0137 (8)	0.0007 (7)
C12	0.0280 (9)	0.0189 (8)	0.0365 (10)	0.0015 (7)	0.0116 (8)	−0.0030 (7)
C13	0.0257 (8)	0.0212 (8)	0.0224 (8)	−0.0008 (7)	0.0085 (6)	0.0008 (6)
C14	0.0217 (8)	0.0193 (8)	0.0346 (9)	−0.0008 (7)	0.0109 (7)	0.0007 (7)
C15	0.0229 (8)	0.0206 (8)	0.0299 (9)	0.0021 (6)	0.0075 (7)	0.0005 (7)
C16	0.0265 (9)	0.0236 (9)	0.0456 (11)	−0.0001 (7)	0.0143 (8)	−0.0021 (8)
C17	0.0255 (9)	0.0330 (10)	0.0475 (12)	0.0011 (8)	0.0155 (8)	−0.0029 (8)
C18	0.0255 (9)	0.0328 (10)	0.0416 (10)	0.0085 (8)	0.0087 (8)	−0.0040 (8)
C19	0.0311 (10)	0.0226 (9)	0.0445 (11)	0.0062 (7)	0.0070 (8)	−0.0002 (8)
C20	0.0250 (8)	0.0219 (9)	0.0353 (9)	0.0019 (7)	0.0070 (7)	0.0010 (7)

Geometric parameters (Å, º)

Cl1—C18	1.7385 (19)	C7—C8	1.504 (2)
Cl2—C20	1.7373 (18)	C8—C14	1.352 (2)
S1—C8	1.7321 (17)	C9—C10	1.518 (2)
S1—C1	1.7430 (17)	C9—H9A	1.01 (2)
O1—C7	1.227 (2)	C9—H9B	0.97 (2)
O2—C13	1.364 (2)	C10—H10A	1.01 (2)
O2—C12	1.453 (2)	C10—H10B	0.99 (2)
O3—C13	1.211 (2)	C11—C12	1.522 (2)
N1—C7	1.374 (2)	C11—H11A	0.98 (2)
N1—C6	1.418 (2)	C11—H11B	0.97 (3)
N1—C9	1.473 (2)	C12—H12A	0.97 (2)
N2—C13	1.349 (2)	C12—H12B	0.95 (2)
N2—C11	1.448 (2)	C14—C15	1.455 (2)
N2—C10	1.451 (2)	C14—H14	0.96 (2)
C1—C2	1.394 (2)	C15—C16	1.406 (2)
C1—C6	1.397 (2)	C15—C20	1.411 (2)
C2—C3	1.378 (3)	C16—C17	1.386 (3)
C2—H2	0.94 (2)	C16—H16	0.97 (3)
C3—C4	1.388 (3)	C17—C18	1.377 (3)
C3—H3	0.94 (3)	C17—H17	0.95 (3)
C4—C5	1.384 (3)	C18—C19	1.387 (3)
C4—H4	0.94 (2)	C19—C20	1.385 (3)
C5—C6	1.404 (2)	C19—H19	0.96 (2)
C5—H5	0.93 (2)
Cl1···S1^i	3.5625 (7)	O3···H10B	2.61 (2)
Cl2···C12^ii	3.470 (2)	O3···H5^ii	2.78 (2)
Cl2···C3^iii	3.557 (2)	O3···H11B^ii	2.80 (2)
Cl2···O2^ii	3.3371 (13)	O3···H9A^v	2.73 (2)
Cl1···H3^iv	3.01 (3)	O3···H9B^v	2.90 (2)
Cl1···H16^i	2.97 (3)	O3···H11A^vi	2.82 (2)
Cl2···H14	2.51 (2)	N2···O3^vi	3.165 (2)
Cl2···H4^iii	3.12 (2)	N2···C13^vi	3.190 (2)
Cl2···H12A^ii	3.15 (2)	N2···H9B^v	2.91 (2)
Cl2···H3^iii	2.97 (3)	C5···C10	3.422 (3)
S1···N1	3.1231 (14)	C7···C12^v	3.580 (3)
S1···C16	3.136 (2)	C9···C13^v	3.287 (2)
S1···H16	2.45 (2)	C10···C13^vi	3.369 (2)
O1···C10	3.187 (2)	C13···C13^vi	3.320 (2)
O1···C12^ii	3.038 (2)	C5···H10A	2.97 (2)
O1···C12^v	3.304 (3)	C5···H9A	2.53 (2)
O2···C10^vi	3.255 (2)	C7···H10B	2.99 (2)
O2···C7^v	3.143 (2)	C8···H16	2.99 (2)
O3···N2^vi	3.165 (2)	C9···H5	2.52 (2)
O3···C11^vi	3.328 (3)	C9···H9B^v	2.92 (2)
O3···C11^ii	3.375 (2)	C10···H5	2.92 (2)
O3···C9^v	3.196 (2)	C13···H9B^v	2.70 (2)
O1···H12B^ii	2.75 (2)	C14···H12B^v	2.98 (2)
O1···H9B	2.23 (2)	H5···H9A	2.06 (3)
O1···H10B	2.73 (2)	H5···H10A	2.49 (3)
O1···H12A^ii	2.74 (2)	H9A···H11B	2.58 (3)
O1···H12B^v	2.79 (2)	H9B···H9B^v	2.26 (3)
O1···H14	2.23 (2)	H10A···H11A	2.58 (3)
O2···H10B^vi	2.75 (2)	H10B···H12A^vi	2.45 (3)
O2···H4^ii	2.62 (2)	H12A···H10B^vi	2.45 (3)
C8—S1—C1	104.29 (8)	C9—C10—H10A	110.3 (12)
C13—O2—C12	109.43 (13)	N2—C10—H10B	109.8 (13)
C7—N1—C6	126.86 (14)	C9—C10—H10B	108.4 (13)
C7—N1—C9	114.42 (14)	H10A—C10—H10B	107.1 (17)
C6—N1—C9	118.72 (14)	N2—C11—C12	101.36 (14)
C13—N2—C11	113.07 (14)	N2—C11—H11A	110.5 (13)
C13—N2—C10	123.45 (15)	C12—C11—H11A	112.7 (14)
C11—N2—C10	123.45 (14)	N2—C11—H11B	111.1 (14)
C2—C1—C6	120.75 (16)	C12—C11—H11B	112.3 (14)
C2—C1—S1	115.20 (13)	H11A—C11—H11B	108.8 (19)
C6—C1—S1	123.97 (13)	O2—C12—C11	105.47 (13)
C3—C2—C1	120.61 (17)	O2—C12—H12A	108.2 (14)
C3—C2—H2	122.4 (14)	C11—C12—H12A	110.6 (13)
C1—C2—H2	117.0 (14)	O2—C12—H12B	106.3 (14)
C2—C3—C4	119.33 (17)	C11—C12—H12B	112.9 (14)
C2—C3—H3	119.4 (15)	H12A—C12—H12B	113.0 (19)
C4—C3—H3	121.2 (15)	O3—C13—N2	128.64 (16)
C5—C4—C3	120.53 (17)	O3—C13—O2	122.07 (15)
C5—C4—H4	119.3 (14)	N2—C13—O2	109.30 (14)
C3—C4—H4	120.1 (14)	C8—C14—C15	131.80 (16)
C4—C5—C6	120.93 (16)	C8—C14—H14	113.7 (13)
C4—C5—H5	117.9 (14)	C15—C14—H14	114.5 (13)
C6—C5—H5	121.2 (14)	C16—C15—C20	115.34 (16)
C1—C6—C5	117.79 (15)	C16—C15—C14	125.33 (16)
C1—C6—N1	121.60 (15)	C20—C15—C14	119.31 (16)
C5—C6—N1	120.60 (15)	C17—C16—C15	122.84 (18)
O1—C7—N1	119.71 (15)	C17—C16—H16	114.8 (15)
O1—C7—C8	119.48 (15)	C15—C16—H16	122.4 (15)
N1—C7—C8	120.77 (14)	C18—C17—C16	118.95 (18)
C14—C8—C7	115.16 (15)	C18—C17—H17	118.7 (16)
C14—C8—S1	123.40 (13)	C16—C17—H17	122.4 (16)
C7—C8—S1	121.39 (12)	C17—C18—C19	121.36 (17)
N1—C9—C10	112.06 (14)	C17—C18—Cl1	119.91 (15)
N1—C9—H9A	109.0 (12)	C19—C18—Cl1	118.70 (15)
C10—C9—H9A	113.1 (12)	C20—C19—C18	118.45 (18)
N1—C9—H9B	106.8 (12)	C20—C19—H19	118.9 (13)
C10—C9—H9B	108.7 (12)	C18—C19—H19	122.7 (13)
H9A—C9—H9B	106.9 (16)	C19—C20—C15	123.05 (17)
N2—C10—C9	110.45 (14)	C19—C20—Cl2	116.31 (14)
N2—C10—H10A	110.7 (12)	C15—C20—Cl2	120.64 (13)
C8—S1—C1—C2	−175.06 (14)	C11—N2—C10—C9	81.1 (2)
C8—S1—C1—C6	8.14 (18)	N1—C9—C10—N2	−175.21 (14)
C6—C1—C2—C3	0.3 (3)	C13—N2—C11—C12	−8.6 (2)
S1—C1—C2—C3	−176.63 (16)	C10—N2—C11—C12	173.17 (16)
C1—C2—C3—C4	−1.5 (3)	C13—O2—C12—C11	−10.95 (19)
C2—C3—C4—C5	0.6 (3)	N2—C11—C12—O2	11.27 (19)
C3—C4—C5—C6	1.5 (3)	C11—N2—C13—O3	−177.18 (18)
C2—C1—C6—C5	1.8 (3)	C10—N2—C13—O3	1.1 (3)
S1—C1—C6—C5	178.44 (13)	C11—N2—C13—O2	2.2 (2)
C2—C1—C6—N1	−177.45 (16)	C10—N2—C13—O2	−179.56 (15)
S1—C1—C6—N1	−0.8 (2)	C12—O2—C13—O3	−174.76 (16)
C4—C5—C6—C1	−2.7 (3)	C12—O2—C13—N2	5.81 (18)
C4—C5—C6—N1	176.56 (16)	C7—C8—C14—C15	−176.93 (18)
C7—N1—C6—C1	−9.1 (3)	S1—C8—C14—C15	0.3 (3)
C9—N1—C6—C1	172.24 (16)	C8—C14—C15—C16	6.6 (3)
C7—N1—C6—C5	171.68 (17)	C8—C14—C15—C20	−175.08 (19)
C9—N1—C6—C5	−7.0 (2)	C20—C15—C16—C17	0.6 (3)
C6—N1—C7—O1	−173.69 (16)	C14—C15—C16—C17	179.02 (19)
C9—N1—C7—O1	5.0 (2)	C15—C16—C17—C18	−0.3 (3)
C6—N1—C7—C8	8.7 (3)	C16—C17—C18—C19	0.1 (3)
C9—N1—C7—C8	−172.58 (15)	C16—C17—C18—Cl1	−178.22 (16)
O1—C7—C8—C14	0.9 (3)	C17—C18—C19—C20	−0.3 (3)
N1—C7—C8—C14	178.52 (16)	Cl1—C18—C19—C20	178.04 (15)
O1—C7—C8—S1	−176.37 (14)	C18—C19—C20—C15	0.7 (3)
N1—C7—C8—S1	1.2 (2)	C18—C19—C20—Cl2	−178.85 (15)
C1—S1—C8—C14	174.78 (16)	C16—C15—C20—C19	−0.8 (3)
C1—S1—C8—C7	−8.17 (17)	C14—C15—C20—C19	−179.34 (18)
C7—N1—C9—C10	−88.22 (19)	C16—C15—C20—Cl2	178.68 (14)
C6—N1—C9—C10	90.61 (19)	C14—C15—C20—Cl2	0.2 (2)
C13—N2—C10—C9	−97.0 (2)

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