Crystal structure, Hirshfeld surface analysis and inter­action energy, DFT and anti­bacterial activity studies of ethyl 2-[(2Z)-2-(2-chloro­benzyl­idene)-3-oxo-3,4-di­hydro-2H-1,4-benzo­thia­zin-4-yl]acetate

The di­hydro­benzo­thia­zine ring is distinctly folded across the S...N axis and a puckering analysis of its conformation was performed. In the crystal, two sets of weak C—H_Ph...O_Dbt (Ph = phenyl and Dbt = di­hydro­benzo­thia­zine) hydrogen bonds form layers parallel to the bc plane. The layers stack along the a-axis direction with inter­calation of the ester chains.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.101
• Data-to-parameter ratio = 88.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report

Alert level G
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         36 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 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), CELL_NOW (Sheldrick, 2008a); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Ethyl 2-[(2Z)-2-(2-chlorobenzylidene)-3-oxo-3,4-dihydro-2H-\ 1,4-benzothiazin-4-yl]acetate

Crystal data

C19H16ClNO3S	F(000) = 776
Mr = 373.84	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 11.6882 (2) Å	Cell parameters from 9820 reflections
b = 9.0903 (2) Å	θ = 3.9–74.6°
c = 16.9533 (3) Å	µ = 3.22 mm^−1
β = 105.105 (1)°	T = 150 K
V = 1739.04 (6) Å^3	Block, colourless
Z = 4	0.19 × 0.15 × 0.11 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	25761 independent reflections
Radiation source: INCOATEC IµS micro–focus source	21950 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4167 pixels mm^-1	θmax = 74.6°, θmin = 3.9°
ω scans	h = −14→13
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −11→10
Tmin = 0.57, Tmax = 0.72	l = −21→21
25761 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)] = 0.039	All H-atom parameters refined
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.4043P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
25761 reflections	Δρmax = 0.72 e Å^−3
292 parameters	Δρmin = −0.80 e Å^−3
0 restraints	Extinction correction: SHELXL2018/1 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual space	Extinction coefficient: 0.0032 (6)

Special details

Experimental. Analysis of 529 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008a) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the b axis. The raw data were processed using the multi- component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

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. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
Cl1	0.50488 (5)	0.51497 (7)	0.19568 (3)	0.03952 (18)
S1	0.44083 (4)	0.78070 (6)	0.47131 (3)	0.02735 (16)
O1	0.31103 (13)	0.39288 (15)	0.41536 (8)	0.0264 (3)
O2	0.05392 (14)	0.49512 (17)	0.29883 (9)	0.0341 (4)
O3	−0.04896 (13)	0.37965 (16)	0.37586 (9)	0.0306 (3)
N1	0.21745 (14)	0.60019 (17)	0.43805 (10)	0.0223 (3)
C1	0.19875 (18)	0.7541 (2)	0.42964 (11)	0.0216 (4)
C2	0.08488 (19)	0.8137 (2)	0.40863 (13)	0.0272 (4)
H2	0.019 (2)	0.750 (3)	0.3964 (15)	0.032 (6)*
C3	0.0683 (2)	0.9646 (2)	0.40245 (13)	0.0299 (5)
H3	−0.010 (3)	1.002 (3)	0.3866 (16)	0.038 (7)*
C4	0.1643 (2)	1.0587 (2)	0.41608 (13)	0.0294 (5)
H4	0.152 (3)	1.159 (3)	0.4110 (17)	0.045 (7)*
C5	0.2778 (2)	1.0009 (2)	0.43568 (13)	0.0274 (4)
H5	0.345 (2)	1.066 (3)	0.4429 (15)	0.033 (6)*
C6	0.29556 (17)	0.8496 (2)	0.44327 (11)	0.0228 (4)
C7	0.41573 (18)	0.6168 (2)	0.41447 (11)	0.0224 (4)
C8	0.31254 (18)	0.5270 (2)	0.42214 (11)	0.0214 (4)
C9	0.48358 (18)	0.5650 (2)	0.36782 (12)	0.0239 (4)
H9	0.461 (2)	0.474 (3)	0.3411 (15)	0.030 (6)*
C10	0.58341 (18)	0.6384 (2)	0.34694 (12)	0.0230 (4)
C11	0.59934 (19)	0.6260 (2)	0.26787 (12)	0.0266 (4)
C12	0.6869 (2)	0.7022 (2)	0.24392 (13)	0.0308 (5)
H12	0.693 (2)	0.689 (3)	0.1896 (16)	0.039 (7)*
C13	0.7644 (2)	0.7914 (2)	0.29922 (13)	0.0316 (5)
H13	0.826 (3)	0.842 (3)	0.2818 (17)	0.042 (7)*
C14	0.75389 (19)	0.8019 (2)	0.37885 (13)	0.0281 (4)
H14	0.808 (2)	0.863 (3)	0.4187 (16)	0.037 (7)*
C15	0.66479 (18)	0.7271 (2)	0.40190 (12)	0.0255 (4)
H15	0.659 (2)	0.733 (2)	0.4564 (15)	0.027 (6)*
C16	0.11979 (18)	0.5077 (2)	0.44607 (12)	0.0235 (4)
H16A	0.151 (2)	0.421 (3)	0.4763 (15)	0.029 (6)*
H16B	0.077 (2)	0.556 (3)	0.4769 (14)	0.026 (6)*
C17	0.03970 (18)	0.4622 (2)	0.36420 (12)	0.0244 (4)
C18	−0.1348 (2)	0.3263 (3)	0.30254 (15)	0.0386 (5)
H18A	−0.092 (3)	0.255 (3)	0.2763 (18)	0.048 (8)*
H18B	−0.161 (3)	0.410 (3)	0.2641 (19)	0.049 (8)*
C19	−0.2350 (3)	0.2585 (4)	0.3297 (2)	0.0509 (7)
H19A	−0.205 (3)	0.173 (3)	0.370 (2)	0.054 (8)*
H19B	−0.289 (3)	0.220 (4)	0.283 (2)	0.069 (10)*
H19C	−0.274 (3)	0.331 (4)	0.359 (2)	0.061 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0417 (4)	0.0478 (3)	0.0343 (3)	−0.0153 (2)	0.0194 (2)	−0.0140 (2)
S1	0.0165 (3)	0.0318 (3)	0.0341 (3)	−0.00303 (19)	0.0072 (2)	−0.0083 (2)
O1	0.0279 (8)	0.0251 (7)	0.0300 (7)	−0.0012 (6)	0.0143 (6)	0.0008 (5)
O2	0.0335 (9)	0.0442 (9)	0.0270 (7)	−0.0083 (7)	0.0122 (7)	0.0003 (6)
O3	0.0253 (8)	0.0361 (8)	0.0318 (7)	−0.0111 (6)	0.0100 (6)	−0.0034 (6)
N1	0.0180 (8)	0.0251 (8)	0.0265 (8)	−0.0032 (6)	0.0104 (7)	0.0002 (6)
C1	0.0196 (10)	0.0247 (9)	0.0226 (8)	−0.0025 (8)	0.0093 (8)	−0.0020 (7)
C2	0.0178 (10)	0.0308 (10)	0.0340 (10)	−0.0033 (8)	0.0086 (8)	−0.0031 (8)
C3	0.0215 (11)	0.0327 (11)	0.0357 (11)	0.0027 (9)	0.0080 (9)	−0.0027 (9)
C4	0.0296 (12)	0.0246 (10)	0.0357 (11)	0.0008 (9)	0.0117 (9)	−0.0024 (8)
C5	0.0238 (11)	0.0282 (10)	0.0323 (10)	−0.0061 (8)	0.0108 (9)	−0.0064 (8)
C6	0.0170 (10)	0.0287 (10)	0.0241 (9)	−0.0019 (8)	0.0083 (8)	−0.0036 (7)
C7	0.0190 (10)	0.0253 (9)	0.0236 (9)	−0.0012 (7)	0.0072 (8)	0.0016 (7)
C8	0.0200 (10)	0.0274 (10)	0.0184 (8)	−0.0010 (8)	0.0076 (7)	0.0006 (7)
C9	0.0217 (10)	0.0254 (10)	0.0262 (9)	−0.0004 (8)	0.0094 (8)	0.0020 (8)
C10	0.0191 (10)	0.0252 (9)	0.0275 (9)	0.0040 (7)	0.0111 (8)	0.0039 (7)
C11	0.0243 (11)	0.0282 (10)	0.0300 (10)	0.0001 (8)	0.0121 (9)	−0.0012 (8)
C12	0.0313 (12)	0.0368 (12)	0.0298 (10)	−0.0013 (9)	0.0177 (9)	0.0006 (9)
C13	0.0249 (11)	0.0386 (12)	0.0359 (11)	−0.0044 (9)	0.0164 (9)	0.0038 (9)
C14	0.0181 (10)	0.0374 (11)	0.0296 (10)	−0.0027 (9)	0.0072 (8)	0.0006 (9)
C15	0.0196 (10)	0.0333 (10)	0.0248 (9)	0.0022 (8)	0.0083 (8)	0.0038 (8)
C16	0.0208 (10)	0.0267 (10)	0.0268 (9)	−0.0039 (8)	0.0129 (8)	0.0003 (8)
C17	0.0212 (10)	0.0239 (9)	0.0307 (10)	−0.0017 (8)	0.0114 (8)	−0.0017 (8)
C18	0.0306 (13)	0.0435 (13)	0.0387 (12)	−0.0113 (11)	0.0033 (10)	−0.0085 (11)
C19	0.0319 (15)	0.0561 (17)	0.0614 (17)	−0.0187 (13)	0.0065 (14)	−0.0055 (15)

Geometric parameters (Å, º)

Cl1—C11	1.741 (2)	C9—C10	1.465 (3)
S1—C6	1.755 (2)	C9—H9	0.95 (2)
S1—C7	1.757 (2)	C10—C15	1.401 (3)
O1—C8	1.224 (2)	C10—C11	1.405 (3)
O2—C17	1.200 (2)	C11—C12	1.382 (3)
O3—C17	1.335 (2)	C12—C13	1.383 (3)
O3—C18	1.462 (3)	C12—H12	0.95 (3)
N1—C8	1.381 (2)	C13—C14	1.390 (3)
N1—C1	1.417 (2)	C13—H13	0.96 (3)
N1—C16	1.452 (2)	C14—C15	1.382 (3)
C1—C2	1.395 (3)	C14—H14	0.97 (3)
C1—C6	1.397 (3)	C15—H15	0.95 (2)
C2—C3	1.386 (3)	C16—C17	1.515 (3)
C2—H2	0.95 (3)	C16—H16A	0.96 (3)
C3—C4	1.382 (3)	C16—H16B	0.92 (3)
C3—H3	0.94 (3)	C18—C19	1.498 (4)
C4—C5	1.384 (3)	C18—H18A	0.99 (3)
C4—H4	0.93 (3)	C18—H18B	1.00 (3)
C5—C6	1.392 (3)	C19—H19A	1.03 (3)
C5—H5	0.96 (3)	C19—H19B	0.94 (4)
C7—C9	1.343 (3)	C19—H19C	1.00 (4)
C7—C8	1.490 (3)
Cl1···C14^i	3.5363 (9)	O1···H12^i	2.560 (9)
Cl1···S1^i	3.7268 (3)	O1···H15^ii	2.400 (8)
Cl1···C10^i	3.5940 (7)	O2···H18B	2.545 (11)
Cl1···C15^i	3.4359 (7)	O2···H13^i	2.606 (10)
Cl1···H9	2.674 (8)	O2···H18A	2.74 (3)
S1···N1	3.0100 (6)	O3···H16B^vi	2.666 (8)
S1···C15	3.1748 (8)	C2···C17	3.2932 (10)
S1···O1^ii	3.4189 (6)	C4···C14^iii	3.5882 (12)
S1···H15	2.660 (10)	C2···H16B	2.621 (8)
S1···H5^iii	2.906 (9)	C4···H14^iii	2.826 (10)
O1···C17	3.1263 (9)	C4···H12^vii	2.993 (10)
O1···C12^i	3.2141 (10)	C5···H12^vii	2.817 (10)
O1···C15^ii	3.2268 (8)	C7···H15	2.937 (9)
O2···N1	2.7902 (7)	C15···H16A^ii	2.900 (9)
O2···C8	3.2091 (9)	C16···H16B^vi	2.987 (9)
O2···C1	3.3715 (8)	C16···H2	2.538 (9)
O2···C3^iv	3.3498 (10)	C17···H2	2.696 (9)
O2···C2	3.4103 (9)	H2···H16B	2.223 (12)
O1···H9	2.516 (9)	H5···H12^vii	2.444 (13)
O1···H16A	2.376 (9)	H5···H15^iii	2.509 (12)
O1···H4^v	2.806 (11)	H16B···H16B^vi	2.381 (13)
C6—S1—C7	98.19 (9)	C12—C11—Cl1	117.82 (16)
C17—O3—C18	116.60 (16)	C10—C11—Cl1	119.98 (16)
C8—N1—C1	124.52 (15)	C11—C12—C13	119.92 (19)
C8—N1—C16	115.56 (16)	C11—C12—H12	118.0 (16)
C1—N1—C16	118.47 (16)	C13—C12—H12	122.0 (16)
C2—C1—C6	118.60 (18)	C12—C13—C14	119.4 (2)
C2—C1—N1	121.41 (17)	C12—C13—H13	118.8 (16)
C6—C1—N1	120.00 (17)	C14—C13—H13	121.8 (16)
C3—C2—C1	120.63 (19)	C15—C14—C13	120.3 (2)
C3—C2—H2	120.0 (15)	C15—C14—H14	119.2 (16)
C1—C2—H2	119.4 (15)	C13—C14—H14	120.5 (16)
C4—C3—C2	120.6 (2)	C14—C15—C10	121.74 (18)
C4—C3—H3	120.2 (16)	C14—C15—H15	120.3 (15)
C2—C3—H3	119.2 (16)	C10—C15—H15	118.0 (15)
C3—C4—C5	119.4 (2)	N1—C16—C17	112.65 (16)
C3—C4—H4	120.0 (18)	N1—C16—H16A	109.1 (15)
C5—C4—H4	120.6 (18)	C17—C16—H16A	109.0 (14)
C4—C5—C6	120.5 (2)	N1—C16—H16B	109.1 (15)
C4—C5—H5	119.4 (15)	C17—C16—H16B	110.8 (15)
C6—C5—H5	120.1 (15)	H16A—C16—H16B	106 (2)
C5—C6—C1	120.27 (18)	O2—C17—O3	125.18 (19)
C5—C6—S1	119.21 (15)	O2—C17—C16	125.21 (18)
C1—C6—S1	120.51 (15)	O3—C17—C16	109.61 (16)
C9—C7—C8	118.34 (17)	O3—C18—C19	107.0 (2)
C9—C7—S1	125.50 (16)	O3—C18—H18A	106.6 (17)
C8—C7—S1	116.11 (14)	C19—C18—H18A	113.0 (17)
O1—C8—N1	120.36 (17)	O3—C18—H18B	109.1 (17)
O1—C8—C7	121.99 (17)	C19—C18—H18B	112.6 (18)
N1—C8—C7	117.64 (16)	H18A—C18—H18B	108 (2)
C7—C9—C10	127.75 (19)	C18—C19—H19A	111.0 (18)
C7—C9—H9	116.7 (15)	C18—C19—H19B	108 (2)
C10—C9—H9	115.3 (15)	H19A—C19—H19B	109 (3)
C15—C10—C11	116.42 (18)	C18—C19—H19C	112.1 (19)
C15—C10—C9	123.16 (17)	H19A—C19—H19C	107 (2)
C11—C10—C9	120.39 (18)	H19B—C19—H19C	111 (3)
C12—C11—C10	122.19 (19)
C8—N1—C1—C2	149.38 (19)	C9—C7—C8—N1	−152.68 (18)
C16—N1—C1—C2	−16.2 (3)	S1—C7—C8—N1	29.5 (2)
C8—N1—C1—C6	−31.3 (3)	C8—C7—C9—C10	175.30 (18)
C16—N1—C1—C6	163.13 (17)	S1—C7—C9—C10	−7.1 (3)
C6—C1—C2—C3	−0.8 (3)	C7—C9—C10—C15	37.4 (3)
N1—C1—C2—C3	178.55 (18)	C7—C9—C10—C11	−140.4 (2)
C1—C2—C3—C4	0.8 (3)	C15—C10—C11—C12	−2.9 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	175.1 (2)
C3—C4—C5—C6	−1.3 (3)	C15—C10—C11—Cl1	178.57 (15)
C4—C5—C6—C1	1.2 (3)	C9—C10—C11—Cl1	−3.5 (3)
C4—C5—C6—S1	−178.03 (16)	C10—C11—C12—C13	1.7 (3)
C2—C1—C6—C5	−0.2 (3)	Cl1—C11—C12—C13	−179.76 (18)
N1—C1—C6—C5	−179.53 (17)	C11—C12—C13—C14	0.7 (3)
C2—C1—C6—S1	179.07 (15)	C12—C13—C14—C15	−1.8 (3)
N1—C1—C6—S1	−0.3 (2)	C13—C14—C15—C10	0.5 (3)
C7—S1—C6—C5	−146.23 (16)	C11—C10—C15—C14	1.8 (3)
C7—S1—C6—C1	34.53 (17)	C9—C10—C15—C14	−176.10 (19)
C6—S1—C7—C9	134.12 (18)	C8—N1—C16—C17	−80.3 (2)
C6—S1—C7—C8	−48.28 (16)	C1—N1—C16—C17	86.5 (2)
C1—N1—C8—O1	−165.71 (18)	C18—O3—C17—O2	−0.1 (3)
C16—N1—C8—O1	0.3 (3)	C18—O3—C17—C16	−179.95 (18)
C1—N1—C8—C7	14.8 (3)	N1—C16—C17—O2	1.2 (3)
C16—N1—C8—C7	−179.20 (16)	N1—C16—C17—O3	−179.02 (16)
C9—C7—C8—O1	27.9 (3)	C17—O3—C18—C19	−171.0 (2)
S1—C7—C8—O1	−149.91 (15)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1^vii	0.95 (3)	2.56 (3)	3.214 (2)	126 (2)
C15—H15···O1^ii	0.95 (2)	2.40 (2)	3.227 (2)	145.8 (15)

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