5-[(6-Fluoro-1,3-benzothia­zol-2-ylamino)methyl­ene]-2,2-dimethyl-1,3-dioxane-4,6-dione

In the title compound, C₂₀H₁₆N₂O₄S, the 1,3-dioxane-4,6-dione ring exhibits a half-chair conformation. The amino H atom forms an intra­molecular contact to a carbonyl O atom, forming a six-membered ring, and an inter­molecular contact to a carbonyl O atom. Additional inter­molecular hydrogen bonds of the the types C—H...O and C—H...F are also observed.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.094
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-[(6-Fluoro-1,3-benzothiazol-2-ylamino)methylene]-2,2-dimethyl-1,3-dioxane- 4,6-dione

Crystal data

C14H11FN2O4S	F(000) = 664
Mr = 322.31	Dx = 1.556 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.433 (1) Å	θ = 4.6–18.6°
b = 19.532 (2) Å	µ = 2.41 mm^−1
c = 11.218 (2) Å	T = 299 K
β = 102.52 (1)°	Rod, light brown
V = 1376.0 (4) Å^3	0.20 × 0.13 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 67.0°, θmin = 4.5°
Graphite monochromator	h = −7→1
ω/2θ scans	k = −23→0
2707 measured reflections	l = −13→13
2454 independent reflections	3 standard reflections every 120 min
1949 reflections with I > 2σ(I)	intensity decay: 2.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	Only H-atom coordinates refined
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.3778P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.004
2454 reflections	Δρmax = 0.26 e Å^−3
233 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (3)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	1.07160 (8)	−0.04044 (3)	0.17716 (5)	0.04063 (18)
F1	1.8327 (2)	−0.07862 (8)	0.42808 (16)	0.0694 (5)
O1	0.2004 (2)	0.16178 (7)	−0.03010 (14)	0.0392 (4)
O2	0.3669 (2)	0.26855 (7)	0.02415 (13)	0.0383 (4)
O3	0.3780 (2)	0.06384 (7)	0.00090 (14)	0.0436 (4)
O4	0.6901 (2)	0.27516 (8)	0.13867 (16)	0.0506 (4)
N1	1.1530 (3)	0.08694 (8)	0.23835 (16)	0.0380 (4)
N2	0.8093 (3)	0.06921 (9)	0.11746 (16)	0.0351 (4)
H2N	0.713 (4)	0.0399 (12)	0.077 (2)	0.042*
C1	1.0102 (3)	0.04631 (10)	0.17900 (17)	0.0328 (4)
C2	1.3199 (3)	−0.02079 (10)	0.26628 (18)	0.0346 (5)
C3	1.4860 (4)	−0.06573 (12)	0.3119 (2)	0.0431 (5)
H3	1.472 (4)	−0.1130 (13)	0.299 (2)	0.052*
C4	1.6666 (3)	−0.03659 (12)	0.3804 (2)	0.0462 (6)
C5	1.6894 (4)	0.03252 (13)	0.4055 (2)	0.0496 (6)
H5	1.813 (4)	0.0473 (14)	0.453 (2)	0.060*
C6	1.5216 (4)	0.07608 (12)	0.3606 (2)	0.0458 (6)
H6	1.539 (4)	0.1247 (13)	0.380 (2)	0.055*
C7	1.3344 (3)	0.04932 (10)	0.28938 (18)	0.0347 (4)
C8	0.7609 (3)	0.13532 (11)	0.11482 (19)	0.0348 (5)
H8	0.874 (4)	0.1655 (12)	0.153 (2)	0.042*
C9	0.5699 (3)	0.16531 (10)	0.06328 (18)	0.0336 (5)
C10	0.3831 (3)	0.12567 (10)	0.00861 (18)	0.0331 (4)
C11	0.2185 (3)	0.23168 (10)	−0.06809 (19)	0.0344 (5)
C12	0.5542 (3)	0.23906 (10)	0.07853 (18)	0.0351 (5)
C13	0.0058 (4)	0.26480 (13)	−0.0743 (3)	0.0463 (6)
H13A	−0.028 (4)	0.2620 (13)	0.006 (3)	0.056*
H13B	−0.099 (4)	0.2411 (13)	−0.135 (2)	0.056*
H13C	0.013 (4)	0.3128 (14)	−0.097 (2)	0.056*
C14	0.2891 (5)	0.23293 (13)	−0.1872 (2)	0.0482 (6)
H14A	0.281 (4)	0.2825 (14)	−0.219 (2)	0.058*
H14B	0.434 (4)	0.2158 (14)	−0.176 (2)	0.058*
H14C	0.192 (4)	0.2091 (14)	−0.244 (2)	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0360 (3)	0.0299 (3)	0.0492 (3)	0.0010 (2)	−0.0056 (2)	−0.0030 (2)
F1	0.0410 (8)	0.0664 (10)	0.0895 (12)	0.0158 (7)	−0.0104 (7)	0.0166 (8)
O1	0.0329 (8)	0.0304 (7)	0.0488 (9)	0.0002 (6)	−0.0030 (6)	0.0068 (6)
O2	0.0374 (8)	0.0299 (7)	0.0430 (8)	0.0039 (6)	−0.0016 (6)	−0.0045 (6)
O3	0.0437 (9)	0.0269 (7)	0.0547 (9)	−0.0005 (6)	−0.0017 (7)	0.0004 (6)
O4	0.0417 (9)	0.0376 (8)	0.0647 (11)	−0.0015 (7)	−0.0052 (8)	−0.0146 (8)
N1	0.0359 (10)	0.0316 (9)	0.0404 (10)	0.0032 (7)	−0.0051 (8)	−0.0028 (7)
N2	0.0317 (9)	0.0305 (9)	0.0379 (9)	0.0003 (7)	−0.0035 (7)	−0.0018 (7)
C1	0.0328 (10)	0.0319 (10)	0.0314 (10)	0.0032 (8)	0.0018 (8)	0.0006 (8)
C2	0.0319 (11)	0.0359 (10)	0.0339 (11)	0.0001 (8)	0.0024 (8)	0.0018 (8)
C3	0.0409 (12)	0.0369 (12)	0.0490 (13)	0.0066 (10)	0.0040 (10)	0.0051 (10)
C4	0.0316 (11)	0.0531 (14)	0.0496 (13)	0.0091 (10)	−0.0005 (9)	0.0128 (11)
C5	0.0340 (12)	0.0559 (15)	0.0517 (14)	−0.0040 (11)	−0.0066 (10)	0.0050 (11)
C6	0.0423 (13)	0.0389 (12)	0.0495 (13)	−0.0022 (10)	−0.0050 (10)	−0.0026 (10)
C7	0.0346 (10)	0.0342 (10)	0.0327 (10)	0.0014 (8)	0.0015 (8)	0.0013 (8)
C8	0.0343 (11)	0.0330 (10)	0.0345 (11)	−0.0008 (8)	0.0019 (9)	−0.0020 (8)
C9	0.0324 (10)	0.0315 (10)	0.0339 (11)	0.0001 (8)	0.0009 (8)	−0.0017 (8)
C10	0.0341 (10)	0.0313 (10)	0.0316 (10)	0.0021 (8)	0.0024 (8)	0.0033 (8)
C11	0.0363 (11)	0.0279 (10)	0.0352 (11)	0.0000 (8)	−0.0008 (9)	0.0018 (8)
C12	0.0326 (10)	0.0336 (10)	0.0369 (11)	0.0016 (9)	0.0031 (9)	−0.0029 (8)
C13	0.0373 (12)	0.0446 (13)	0.0527 (15)	0.0071 (10)	−0.0001 (11)	0.0038 (11)
C14	0.0609 (16)	0.0452 (13)	0.0379 (13)	0.0039 (12)	0.0092 (11)	0.0021 (10)

Geometric parameters (Å, º)

S1—C2	1.734 (2)	C4—C5	1.380 (3)
S1—C1	1.741 (2)	C5—C6	1.381 (3)
F1—C4	1.362 (2)	C5—H5	0.90 (3)
O1—C10	1.358 (2)	C6—C7	1.394 (3)
O1—C11	1.442 (2)	C6—H6	0.98 (3)
O2—C12	1.356 (2)	C8—C9	1.371 (3)
O2—C11	1.439 (2)	C8—H8	0.96 (2)
O3—C10	1.211 (2)	C9—C10	1.449 (3)
O4—C12	1.209 (2)	C9—C12	1.457 (3)
N1—C1	1.285 (3)	C11—C13	1.501 (3)
N1—C7	1.393 (3)	C11—C14	1.502 (3)
N2—C8	1.327 (3)	C13—H13A	0.97 (3)
N2—C1	1.400 (2)	C13—H13B	0.97 (3)
N2—H2N	0.89 (2)	C13—H13C	0.98 (3)
C2—C3	1.391 (3)	C14—H14A	1.03 (3)
C2—C7	1.393 (3)	C14—H14B	0.97 (3)
C3—C4	1.370 (3)	C14—H14C	0.91 (3)
C3—H3	0.94 (3)
C2—S1—C1	87.75 (9)	N2—C8—H8	115.9 (13)
C10—O1—C11	117.79 (15)	C9—C8—H8	116.6 (13)
C12—O2—C11	119.81 (15)	C8—C9—C10	122.38 (18)
C1—N1—C7	109.16 (17)	C8—C9—C12	116.84 (18)
C8—N2—C1	120.59 (18)	C10—C9—C12	120.38 (18)
C8—N2—H2N	118.5 (15)	O3—C10—O1	119.12 (18)
C1—N2—H2N	120.9 (15)	O3—C10—C9	124.78 (18)
N1—C1—N2	122.53 (18)	O1—C10—C9	116.01 (17)
N1—C1—S1	117.96 (15)	O2—C11—O1	110.15 (15)
N2—C1—S1	119.51 (14)	O2—C11—C13	105.87 (17)
C3—C2—C7	122.46 (19)	O1—C11—C13	106.89 (18)
C3—C2—S1	127.61 (17)	O2—C11—C14	110.49 (18)
C7—C2—S1	109.93 (15)	O1—C11—C14	109.72 (18)
C4—C3—C2	115.7 (2)	C13—C11—C14	113.6 (2)
C4—C3—H3	122.5 (15)	O4—C12—O2	117.93 (18)
C2—C3—H3	121.7 (15)	O4—C12—C9	125.61 (19)
F1—C4—C3	117.9 (2)	O2—C12—C9	116.40 (17)
F1—C4—C5	118.0 (2)	C11—C13—H13A	108.6 (15)
C3—C4—C5	124.1 (2)	C11—C13—H13B	108.5 (15)
C4—C5—C6	119.2 (2)	H13A—C13—H13B	111 (2)
C4—C5—H5	118.2 (18)	C11—C13—H13C	109.2 (16)
C6—C5—H5	122.5 (18)	H13A—C13—H13C	109 (2)
C5—C6—C7	119.2 (2)	H13B—C13—H13C	110 (2)
C5—C6—H6	118.4 (15)	C11—C14—H14A	108.9 (14)
C7—C6—H6	122.4 (15)	C11—C14—H14B	110.4 (15)
N1—C7—C2	115.20 (18)	H14A—C14—H14B	110 (2)
N1—C7—C6	125.48 (19)	C11—C14—H14C	108.5 (17)
C2—C7—C6	119.31 (19)	H14A—C14—H14C	105 (2)
N2—C8—C9	127.56 (19)	H14B—C14—H14C	114 (2)
C7—N1—C1—N2	179.95 (18)	C5—C6—C7—C2	0.8 (4)
C7—N1—C1—S1	0.4 (2)	C1—N2—C8—C9	−177.1 (2)
C8—N2—C1—N1	2.3 (3)	N2—C8—C9—C10	4.0 (4)
C8—N2—C1—S1	−178.18 (17)	N2—C8—C9—C12	176.8 (2)
C2—S1—C1—N1	−0.25 (18)	C11—O1—C10—O3	−154.73 (19)
C2—S1—C1—N2	−179.78 (17)	C11—O1—C10—C9	28.7 (3)
C1—S1—C2—C3	179.4 (2)	C8—C9—C10—O3	−1.5 (3)
C1—S1—C2—C7	−0.03 (16)	C12—C9—C10—O3	−174.1 (2)
C7—C2—C3—C4	−0.6 (3)	C8—C9—C10—O1	174.85 (19)
S1—C2—C3—C4	−179.92 (18)	C12—C9—C10—O1	2.3 (3)
C2—C3—C4—F1	179.3 (2)	C12—O2—C11—O1	44.0 (2)
C2—C3—C4—C5	0.3 (4)	C12—O2—C11—C13	159.25 (18)
F1—C4—C5—C6	−178.5 (2)	C12—O2—C11—C14	−77.4 (2)
C3—C4—C5—C6	0.6 (4)	C10—O1—C11—O2	−50.9 (2)
C4—C5—C6—C7	−1.1 (4)	C10—O1—C11—C13	−165.50 (18)
C1—N1—C7—C2	−0.5 (3)	C10—O1—C11—C14	70.9 (2)
C1—N1—C7—C6	−179.6 (2)	C11—O2—C12—O4	166.97 (19)
C3—C2—C7—N1	−179.2 (2)	C11—O2—C12—C9	−15.7 (3)
S1—C2—C7—N1	0.3 (2)	C8—C9—C12—O4	−4.8 (3)
C3—C2—C7—C6	0.1 (3)	C10—C9—C12—O4	168.2 (2)
S1—C2—C7—C6	179.51 (18)	C8—C9—C12—O2	178.11 (18)
C5—C6—C7—N1	179.9 (2)	C10—C9—C12—O2	−9.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.89 (2)	2.19 (2)	2.801 (2)	125.5 (19)
N2—H2N···O3^i	0.89 (2)	2.23 (2)	3.045 (2)	151 (2)
C3—H3···O4^ii	0.94 (3)	2.58 (3)	3.394 (3)	145 (2)
C5—H5···F1^iii	0.90 (3)	2.46 (3)	3.356 (3)	174 (2)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+4, −y, −z+1.