(Z)-3-Butyl-5-(4-nitro­benzyl­idene)thia­zolidine-2,4-dione

In the title compound, C₁₄H₁₄N₂O₄S, the benzene and thia­zolidine rings are almost coplanar with a dihedral angle of 2.98 (14)°. The butyl chain is directed almost perpendicular to the plane of the rest of the mol­ecule. In the crystal, a combination of C—H...O hydrogen bonds and offset π–π inter­actions leads to the formation of a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.141
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2       --C10      .        5.5 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        S1      0.084 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00433 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     21.014 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.786 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.74 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2017); cell refinement: X-AREA (Stoe & Cie, 2017); data reduction: X-RED32 (Stoe & Cie, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(Z)-3-Butyl-5-(4-nitrobenzylidene)thiazolidine-2,4-dione

Crystal data

C14H14N2O4S	F(000) = 640
Mr = 306.33	Dx = 1.392 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2595 (8) Å	Cell parameters from 9040 reflections
b = 27.492 (3) Å	θ = 1.5–27.5°
c = 7.9630 (9) Å	µ = 0.24 mm^−1
β = 113.072 (8)°	T = 296 K
V = 1462.1 (3) Å^3	Prism, yellow
Z = 4	0.74 × 0.54 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer	2855 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1430 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.078
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.5°
rotation method scans	h = −8→8
Absorption correction: integration (X-RED32 & X-SHAPE; Stoe & Cie, 2017)	k = −33→33
Tmin = 0.833, Tmax = 0.936	l = −9→9
8120 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 0.83	w = 1/[σ^2(Fo^2) + (0.0719P)^2] where P = (Fo^2 + 2Fc^2)/3
2855 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.22 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. H atoms were positioned geometrically and refined as riding: C—H = 0.95–0.98 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

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

	x	y	z	Uiso*/Ueq
S1	0.24335 (11)	0.62282 (3)	0.56254 (11)	0.0773 (3)
O4	0.2873 (3)	0.57655 (7)	1.0303 (3)	0.0904 (6)
N2	0.2667 (3)	0.64894 (8)	0.8866 (3)	0.0700 (6)
O3	0.2360 (3)	0.71142 (7)	0.6862 (3)	0.1027 (7)
N1	0.2171 (4)	0.40379 (12)	0.1189 (4)	0.0844 (7)
O1	0.2111 (4)	0.36052 (9)	0.1416 (4)	0.1175 (9)
C4	0.2562 (3)	0.49850 (9)	0.5495 (3)	0.0611 (6)
C9	0.2755 (4)	0.59888 (10)	0.8958 (4)	0.0673 (7)
C5	0.2708 (4)	0.44824 (9)	0.5746 (4)	0.0665 (7)
H5	0.290385	0.435385	0.688347	0.080*
C8	0.2653 (3)	0.57709 (9)	0.7210 (3)	0.0621 (6)
C1	0.2298 (4)	0.43668 (10)	0.2678 (4)	0.0665 (7)
C2	0.2147 (4)	0.48596 (11)	0.2365 (4)	0.0723 (7)
H2	0.196410	0.498308	0.122312	0.087*
O2	0.2101 (4)	0.42141 (11)	−0.0246 (4)	0.1234 (9)
C7	0.2705 (3)	0.52875 (9)	0.7049 (4)	0.0643 (7)
H7	0.285820	0.511529	0.810095	0.077*
C3	0.2272 (4)	0.51661 (10)	0.3763 (4)	0.0687 (7)
H3	0.216151	0.549995	0.355939	0.082*
C6	0.2567 (4)	0.41738 (10)	0.4346 (4)	0.0700 (7)
H6	0.265227	0.383898	0.452533	0.084*
C10	0.2485 (4)	0.66871 (10)	0.7210 (4)	0.0763 (8)
C12	0.4807 (5)	0.68443 (11)	1.1853 (4)	0.0922 (10)
H12A	0.472121	0.698510	1.293761	0.111*
H12B	0.541145	0.652509	1.217739	0.111*
C11	0.2710 (4)	0.67873 (10)	1.0404 (4)	0.0838 (9)
H11A	0.186205	0.663844	1.094628	0.101*
H11B	0.216699	0.710631	0.995844	0.101*
C13	0.6140 (5)	0.71590 (13)	1.1259 (5)	0.1011 (10)
H13A	0.559680	0.748613	1.102842	0.121*
H13B	0.615268	0.703279	1.012595	0.121*
C14	0.8259 (6)	0.71780 (18)	1.2675 (6)	0.1483 (17)
H14A	0.904272	0.739189	1.226608	0.222*
H14B	0.882969	0.685760	1.285421	0.222*
H14C	0.825022	0.729644	1.380650	0.222*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0841 (5)	0.0659 (4)	0.0764 (5)	−0.0032 (4)	0.0254 (4)	0.0078 (4)
O4	0.1288 (17)	0.0698 (12)	0.0784 (14)	−0.0099 (11)	0.0470 (13)	−0.0031 (11)
N2	0.0716 (14)	0.0561 (13)	0.0759 (16)	−0.0010 (10)	0.0219 (12)	−0.0029 (11)
O3	0.1218 (19)	0.0604 (12)	0.1050 (17)	0.0011 (12)	0.0217 (14)	0.0097 (11)
N1	0.0743 (16)	0.097 (2)	0.079 (2)	−0.0081 (14)	0.0262 (14)	−0.0152 (16)
O1	0.153 (2)	0.0897 (17)	0.108 (2)	0.0012 (15)	0.0479 (17)	−0.0265 (14)
C4	0.0503 (13)	0.0654 (15)	0.0647 (17)	−0.0007 (11)	0.0197 (12)	−0.0018 (13)
C9	0.0637 (16)	0.0611 (16)	0.074 (2)	−0.0042 (12)	0.0232 (14)	0.0008 (14)
C5	0.0719 (17)	0.0616 (15)	0.0631 (17)	0.0063 (12)	0.0234 (14)	0.0069 (13)
C8	0.0521 (14)	0.0637 (15)	0.0671 (17)	−0.0018 (11)	0.0199 (12)	0.0027 (13)
C1	0.0543 (14)	0.0772 (18)	0.0669 (18)	−0.0048 (13)	0.0225 (13)	−0.0105 (14)
C2	0.0685 (17)	0.0858 (19)	0.0609 (17)	−0.0074 (15)	0.0234 (14)	0.0074 (15)
O2	0.165 (2)	0.133 (2)	0.0874 (18)	−0.0173 (17)	0.0648 (17)	−0.0174 (16)
C7	0.0620 (15)	0.0600 (15)	0.0683 (17)	0.0011 (12)	0.0228 (13)	0.0056 (13)
C3	0.0721 (17)	0.0674 (15)	0.0660 (17)	−0.0020 (13)	0.0263 (14)	0.0053 (14)
C6	0.0688 (17)	0.0653 (15)	0.0713 (18)	0.0054 (13)	0.0225 (14)	0.0017 (14)
C10	0.0645 (18)	0.0643 (18)	0.087 (2)	−0.0018 (13)	0.0157 (15)	0.0029 (15)
C12	0.107 (3)	0.0734 (19)	0.083 (2)	0.0020 (18)	0.023 (2)	−0.0097 (16)
C11	0.091 (2)	0.0665 (17)	0.094 (2)	−0.0030 (15)	0.0355 (18)	−0.0133 (16)
C13	0.083 (2)	0.107 (2)	0.103 (3)	−0.0017 (19)	0.025 (2)	−0.015 (2)
C14	0.088 (3)	0.196 (4)	0.128 (4)	−0.009 (3)	0.006 (2)	−0.038 (3)

Geometric parameters (Å, º)

S1—C8	1.744 (3)	C1—C2	1.374 (4)
S1—C10	1.774 (3)	C2—C3	1.371 (4)
O4—C9	1.208 (3)	C2—H2	0.9300
N2—C9	1.378 (3)	C7—H7	0.9300
N2—C10	1.384 (4)	C3—H3	0.9300
N2—C11	1.463 (3)	C6—H6	0.9300
O3—C10	1.202 (3)	C12—C13	1.506 (4)
N1—O1	1.207 (3)	C12—C11	1.516 (4)
N1—O2	1.223 (3)	C12—H12A	0.9700
N1—C1	1.466 (4)	C12—H12B	0.9700
C4—C5	1.394 (3)	C11—H11A	0.9700
C4—C3	1.402 (4)	C11—H11B	0.9700
C4—C7	1.461 (3)	C13—C14	1.511 (5)
C9—C8	1.490 (4)	C13—H13A	0.9700
C5—C6	1.373 (4)	C13—H13B	0.9700
C5—H5	0.9300	C14—H14A	0.9600
C8—C7	1.337 (3)	C14—H14B	0.9600
C1—C6	1.371 (4)	C14—H14C	0.9600
C8—S1—C10	91.56 (14)	C1—C6—C5	119.0 (3)
C9—N2—C10	115.3 (2)	C1—C6—H6	120.5
C9—N2—C11	121.9 (3)	C5—C6—H6	120.5
C10—N2—C11	122.7 (2)	O3—C10—N2	125.0 (3)
O1—N1—O2	122.6 (3)	O3—C10—S1	123.5 (3)
O1—N1—C1	118.8 (3)	N2—C10—S1	111.5 (2)
O2—N1—C1	118.6 (3)	C13—C12—C11	113.4 (3)
C5—C4—C3	117.8 (2)	C13—C12—H12A	108.9
C5—C4—C7	117.8 (2)	C11—C12—H12A	108.9
C3—C4—C7	124.4 (2)	C13—C12—H12B	108.9
O4—C9—N2	122.7 (3)	C11—C12—H12B	108.9
O4—C9—C8	125.7 (2)	H12A—C12—H12B	107.7
N2—C9—C8	111.6 (2)	N2—C11—C12	112.4 (2)
C6—C5—C4	121.3 (3)	N2—C11—H11A	109.1
C6—C5—H5	119.4	C12—C11—H11A	109.1
C4—C5—H5	119.4	N2—C11—H11B	109.1
C7—C8—C9	119.8 (2)	C12—C11—H11B	109.1
C7—C8—S1	130.2 (2)	H11A—C11—H11B	107.9
C9—C8—S1	110.06 (18)	C12—C13—C14	112.1 (3)
C6—C1—C2	121.9 (3)	C12—C13—H13A	109.2
C6—C1—N1	119.0 (3)	C14—C13—H13A	109.2
C2—C1—N1	119.1 (3)	C12—C13—H13B	109.2
C3—C2—C1	118.9 (3)	C14—C13—H13B	109.2
C3—C2—H2	120.5	H13A—C13—H13B	107.9
C1—C2—H2	120.5	C13—C14—H14A	109.5
C8—C7—C4	130.7 (2)	C13—C14—H14B	109.5
C8—C7—H7	114.7	H14A—C14—H14B	109.5
C4—C7—H7	114.7	C13—C14—H14C	109.5
C2—C3—C4	121.1 (2)	H14A—C14—H14C	109.5
C2—C3—H3	119.4	H14B—C14—H14C	109.5
C4—C3—H3	119.4
C10—N2—C9—O4	−178.4 (3)	S1—C8—C7—C4	−1.2 (4)
C11—N2—C9—O4	0.0 (4)	C5—C4—C7—C8	178.7 (2)
C10—N2—C9—C8	0.6 (3)	C3—C4—C7—C8	−1.8 (4)
C11—N2—C9—C8	179.0 (2)	C1—C2—C3—C4	0.5 (4)
C3—C4—C5—C6	−0.2 (4)	C5—C4—C3—C2	−0.4 (4)
C7—C4—C5—C6	179.3 (2)	C7—C4—C3—C2	−179.9 (2)
O4—C9—C8—C7	−0.5 (4)	C2—C1—C6—C5	−0.6 (4)
N2—C9—C8—C7	−179.6 (2)	N1—C1—C6—C5	179.3 (2)
O4—C9—C8—S1	178.5 (2)	C4—C5—C6—C1	0.7 (4)
N2—C9—C8—S1	−0.5 (3)	C9—N2—C10—O3	179.0 (3)
C10—S1—C8—C7	179.1 (3)	C11—N2—C10—O3	0.6 (4)
C10—S1—C8—C9	0.19 (18)	C9—N2—C10—S1	−0.5 (3)
O1—N1—C1—C6	7.1 (4)	C11—N2—C10—S1	−178.87 (19)
O2—N1—C1—C6	−173.9 (3)	C8—S1—C10—O3	−179.3 (3)
O1—N1—C1—C2	−173.0 (3)	C8—S1—C10—N2	0.1 (2)
O2—N1—C1—C2	6.0 (4)	C9—N2—C11—C12	79.0 (3)
C6—C1—C2—C3	0.1 (4)	C10—N2—C11—C12	−102.8 (3)
N1—C1—C2—C3	−179.8 (2)	C13—C12—C11—N2	70.2 (3)
C9—C8—C7—C4	177.6 (2)	C11—C12—C13—C14	−175.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···S1	0.93	2.55	3.256 (3)	133
C2—H2···O4^i	0.93	2.45	3.139 (4)	131
C5—H5···O2^ii	0.93	2.60	3.468 (4)	156
C11—H11B···O3^iii	0.97	2.60	3.281 (3)	128

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