(Z)-3-Butyl-5-(4-nitrobenzylidene)thiazolidine-2,4-dione (2024)

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619000944/su4169sup1.cif Contains datablocks I, Global
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314619000944/su4169Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619000944/su4169Isup3.cml Supplementary material

CCDC reference: 1890998

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (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 foundAlert level CPLAT230_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 CheckPLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C13 CheckPLAT260_ALERT_2_C Large Average Ueq of Residue Including S1 0.084 CheckPLAT340_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 CheckPLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.786 CheckPLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 11 ReportPLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 InfoAlert level GPLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.74 mmPLAT066_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

Computing details top

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) andpublCIF (Westrip, 2010).

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

Crystal data

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C₁₄H₁₄N₂O₄S	F(000) = 640
M_r = 306.33	D_x = 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) Å³	Prism, yellow
Z = 4	0.74 × 0.54 × 0.28 mm

Data collection

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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	R_int = 0.078
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.5°
rotation method scans	h = −8→8
Absorption correction: integration (X-RED32 & X-SHAPE; Stoe & Cie, 2017)	k = −33→33
T_min = 0.833, T_max = 0.936	l = −9→9
8120 measured reflections

Refinement

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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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.0719P)²] where P = (F_o² + 2F_c²)/3
2855 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details

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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) and1.2U_eq(C) for other H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

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	x	y	z	U_iso*/U_eq
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 (Å²)

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	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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)

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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)

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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···O4ⁱ	0.93	2.45	3.139 (4)	131
C5—H5···O2ⁱⁱ	0.93	2.60	3.468 (4)	156
C11—H11B···O3ⁱⁱⁱ	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.

(Z)-3-Butyl-5-(4-nitro­benzyl­idene)thia­zolidine-2,4-dione (2024)

Supporting information

Key indicators

checkCIF/PLATON results

(Z)-3-Butyl-5-(4-nitrobenzylidene)thiazolidine-2,4-dione (2024)