7-Chloro­indoline-2,3-dione

Sun, J.; Cai, Z.-S.

doi:10.1107/S1600536809051526

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o25

doi:10.1107/S1600536809051526

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7-Chloroindoline-2,3-dione

Jie Sun ^a,^b and Zai-Sheng Cai ^b ^*

^aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Chemistry, Chemical Engineering and Biotechnology, Donghua University, North Renmin Road No. 2999 Songjiang, Shanghai 201620, People's Republic of China
^*Correspondence e-mail: sunjie5516@126.com

(Received 16 November 2009; accepted 30 November 2009; online 4 December 2009)

There are two molecules in the asymmetric unit of the title compound, C₈H₄ClNO₂. In the crystal, they are linked by N—H⋯O hydrogen bonds, generating centrosymmetric, tetrameric assemblies. A C—H⋯O interaction also occurs.

Related literature

For general background to oxyphenastatin derivatives and further synthetic details, see: Uddin et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₈H₄ClNO₂
M_r = 181.57
Triclinic, $[P \overline 1]$
a = 7.2450 (14) Å
b = 8.6080 (17) Å
c = 12.470 (3) Å
α = 86.95 (3)°
β = 78.02 (3)°
γ = 84.89 (3)°
V = 757.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.876, T_max = 0.956
2988 measured reflections
2749 independent reflections
2051 reflections with I > 2σ(I)
R_int = 0.047
3 standard reflections every 200 reflections
intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.160
S = 1.01
2749 reflections
217 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.86	2.12	2.961 (4)	165
N2—H2B⋯O4ⁱ	0.86	2.10	2.923 (3)	160
C14—H14A⋯O2ⁱⁱ	0.93	2.46	3.385 (4)	172
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051526/hb5233sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051526/hb5233Isup2.hkl

checkCIF report

Related literature top

For general background to oxyphenastatin derivatives and further synthetic details, see: Uddin et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

85 g (0.06 mol) Sodium sulfate and 300 ml water was added into a 1000 ml three mouthed flask, mixed till the sodium sulfate dissolved, then a saturated solution of 18 g (0.11 mol) chloral hydrate was added. While stirring, the mixture of 12.7 g (0.1 mol) p-chloroaniline, 12 ml hydrochloric acid and 100 ml water was dropped to the reaction mixture causing white precipitation. Then 22 g (0.32 mol) hydroxylamine hydrochloride was added and the mixture was heated to 348 K. After 5 h, light yellow precipitation appeared, filtered and washed with water, dried and then added the yellow precipitation into concentrated sulfuric acid (50 ml) in batches at 353 K. Heated to 363 K and stirred for 30 minutes and dumped the mixture into ice water (1000 ml), stirred for 40 minutes, filtered and washed with water to neutral, dried and Yellow blocks of (I) were obtained by slow evaporation of an acetone solution (yield; 90%, m.p. 463 K).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989; data reduction: XCAD4(Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

7-chloroindoline-2,3-dione top

Crystal data top

C₈H₄ClNO₂	Z = 4
M_r = 181.57	F(000) = 368
Triclinic, P1	D_x = 1.593 Mg m⁻³
Hall symbol: -P 1	Melting point: 463K K
a = 7.2450 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6080 (17) Å	Cell parameters from 25 reflections
c = 12.470 (3) Å	θ = 9–13°
α = 86.95 (3)°	µ = 0.45 mm⁻¹
β = 78.02 (3)°	T = 293 K
γ = 84.89 (3)°	Block, yellow
V = 757.2 (3) Å³	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2051 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.047
Graphite monochromator	θ_max = 25.3°, θ_min = 1.7°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.876, T_max = 0.956	l = −14→14
2988 measured reflections	3 standard reflections every 200 reflections
2749 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1P)² + 0.250P] where P = (F_o² + 2F_c²)/3
2749 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.63 e Å⁻³
13 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₈H₄ClNO₂	γ = 84.89 (3)°
M_r = 181.57	V = 757.2 (3) Å³
Triclinic, P1	Z = 4
a = 7.2450 (14) Å	Mo Kα radiation
b = 8.6080 (17) Å	µ = 0.45 mm⁻¹
c = 12.470 (3) Å	T = 293 K
α = 86.95 (3)°	0.30 × 0.20 × 0.10 mm
β = 78.02 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2051 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.047
T_min = 0.876, T_max = 0.956	3 standard reflections every 200 reflections
2988 measured reflections	intensity decay: 1%
2749 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	13 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.01	Δρ_max = 0.63 e Å⁻³
2749 reflections	Δρ_min = −0.29 e Å⁻³
217 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.28644 (18)	0.90528 (12)	0.43418 (10)	0.0839 (4)
N1	0.4403 (4)	0.6203 (3)	0.28727 (19)	0.0415 (6)
H1A	0.4599	0.7099	0.2550	0.050*
O1	0.4519 (4)	0.2163 (3)	0.3096 (2)	0.0731 (8)
O2	0.5909 (4)	0.4581 (3)	0.1488 (2)	0.0662 (7)
C1	0.1629 (6)	0.4991 (7)	0.6003 (3)	0.0780 (13)
H1B	0.1019	0.4674	0.6702	0.094*
C2	0.1735 (5)	0.6597 (6)	0.5739 (3)	0.0701 (11)
H2A	0.1201	0.7328	0.6261	0.084*
C3	0.2638 (5)	0.7090 (4)	0.4697 (3)	0.0541 (9)
C4	0.3423 (4)	0.5985 (4)	0.3954 (2)	0.0393 (7)
C5	0.3300 (4)	0.4400 (4)	0.4231 (3)	0.0462 (8)
C6	0.2399 (5)	0.3892 (5)	0.5258 (3)	0.0636 (11)
H6A	0.2321	0.2834	0.5435	0.076*
C7	0.4285 (5)	0.3544 (4)	0.3265 (3)	0.0472 (8)
C8	0.5004 (4)	0.4814 (4)	0.2399 (3)	0.0441 (7)
Cl2	0.12910 (13)	0.66786 (10)	0.12400 (7)	0.0589 (3)
N2	0.3136 (3)	0.9103 (3)	−0.04844 (19)	0.0353 (5)
H2B	0.3737	0.8832	0.0031	0.042*
O3	0.2217 (4)	1.0991 (3)	−0.2813 (2)	0.0618 (7)
O4	0.4995 (3)	1.1009 (3)	−0.13853 (18)	0.0533 (6)
C9	−0.1833 (5)	0.7602 (4)	−0.1086 (3)	0.0486 (8)
H9A	−0.2948	0.7290	−0.1235	0.058*
C10	−0.0841 (4)	0.8681 (4)	−0.1775 (3)	0.0472 (8)
H10A	−0.1282	0.9111	−0.2384	0.057*
C11	0.0833 (4)	0.9115 (3)	−0.1544 (2)	0.0403 (7)
C12	0.1483 (4)	0.8492 (3)	−0.0617 (2)	0.0352 (6)
C13	0.0469 (4)	0.7416 (3)	0.0075 (2)	0.0414 (7)
C14	−0.1181 (4)	0.6972 (4)	−0.0167 (3)	0.0446 (7)
H14A	−0.1866	0.6243	0.0290	0.053*
C15	0.3646 (4)	1.0178 (4)	−0.1286 (2)	0.0438 (7)
C16	0.2210 (4)	1.0242 (4)	−0.2053 (3)	0.0473 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1048 (9)	0.0609 (6)	0.0837 (8)	0.0087 (6)	−0.0158 (6)	−0.0213 (5)
N1	0.0483 (14)	0.0400 (13)	0.0346 (13)	−0.0113 (11)	−0.0040 (11)	0.0076 (10)
O1	0.102 (2)	0.0405 (14)	0.083 (2)	−0.0138 (13)	−0.0326 (17)	0.0086 (13)
O2	0.0718 (17)	0.0661 (16)	0.0523 (15)	−0.0055 (13)	0.0086 (13)	−0.0098 (12)
C1	0.049 (2)	0.144 (4)	0.040 (2)	−0.025 (2)	−0.0059 (17)	0.025 (2)
C2	0.050 (2)	0.116 (3)	0.0408 (19)	0.003 (2)	−0.0039 (16)	−0.010 (2)
C3	0.0449 (18)	0.073 (2)	0.0444 (18)	−0.0010 (16)	−0.0110 (15)	−0.0040 (16)
C4	0.0342 (15)	0.0512 (17)	0.0333 (15)	−0.0076 (12)	−0.0091 (12)	0.0059 (13)
C5	0.0420 (16)	0.0554 (19)	0.0443 (17)	−0.0175 (14)	−0.0149 (14)	0.0180 (14)
C6	0.054 (2)	0.092 (3)	0.049 (2)	−0.029 (2)	−0.0186 (18)	0.033 (2)
C7	0.0547 (19)	0.0435 (18)	0.0501 (19)	−0.0152 (14)	−0.0237 (16)	0.0084 (14)
C8	0.0424 (17)	0.0451 (17)	0.0440 (18)	−0.0062 (13)	−0.0062 (14)	0.0011 (13)
Cl2	0.0661 (6)	0.0547 (5)	0.0548 (5)	−0.0123 (4)	−0.0093 (4)	0.0095 (4)
N2	0.0392 (13)	0.0354 (12)	0.0323 (12)	−0.0086 (10)	−0.0088 (10)	0.0054 (10)
O3	0.0607 (15)	0.0807 (18)	0.0447 (14)	0.0069 (13)	−0.0190 (12)	0.0044 (13)
O4	0.0564 (14)	0.0499 (13)	0.0496 (13)	−0.0119 (11)	−0.0020 (11)	0.0135 (10)
C9	0.0388 (16)	0.0509 (18)	0.057 (2)	−0.0076 (14)	−0.0067 (15)	−0.0162 (16)
C10	0.0406 (17)	0.0563 (19)	0.0460 (18)	0.0031 (15)	−0.0118 (14)	−0.0118 (15)
C11	0.0371 (15)	0.0433 (16)	0.0394 (16)	−0.0018 (12)	−0.0046 (13)	−0.0074 (13)
C12	0.0326 (14)	0.0329 (14)	0.0371 (15)	−0.0030 (11)	0.0010 (12)	−0.0052 (11)
C13	0.0405 (16)	0.0378 (15)	0.0429 (17)	−0.0050 (12)	0.0005 (13)	−0.0080 (13)
C14	0.0376 (16)	0.0398 (16)	0.0521 (18)	−0.0101 (12)	0.0046 (14)	−0.0058 (13)
C15	0.0442 (17)	0.0437 (16)	0.0406 (16)	−0.0105 (14)	−0.0012 (14)	0.0070 (13)
C16	0.0441 (18)	0.0392 (16)	0.055 (2)	−0.0014 (13)	−0.0017 (15)	−0.0040 (15)

Geometric parameters (Å, º) top

Cl1—C3	1.737 (4)	Cl2—C13	1.749 (3)
N1—C8	1.358 (4)	N2—C15	1.342 (4)
N1—C4	1.399 (4)	N2—C12	1.393 (4)
N1—H1A	0.8600	N2—H2B	0.8600
O1—C7	1.210 (4)	O3—C16	1.116 (4)
O2—C8	1.205 (4)	O4—C15	1.244 (4)
C1—C6	1.362 (6)	C9—C10	1.377 (5)
C1—C2	1.410 (7)	C9—C14	1.394 (5)
C1—H1B	0.9300	C9—H9A	0.9300
C2—C3	1.391 (5)	C10—C11	1.389 (4)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.366 (5)	C11—C12	1.401 (4)
C4—C5	1.396 (4)	C11—C16	1.478 (4)
C5—C6	1.379 (5)	C12—C13	1.384 (4)
C5—C7	1.465 (5)	C13—C14	1.382 (4)
C6—H6A	0.9300	C14—H14A	0.9300
C7—C8	1.541 (4)	C15—C16	1.548 (5)

C8—N1—C4	111.1 (2)	C15—N2—C12	109.5 (2)
C8—N1—H1A	124.5	C15—N2—H2B	125.2
C4—N1—H1A	124.5	C12—N2—H2B	125.2
C6—C1—C2	121.4 (3)	C10—C9—C14	120.5 (3)
C6—C1—H1B	119.3	C10—C9—H9A	119.7
C2—C1—H1B	119.3	C14—C9—H9A	119.7
C3—C2—C1	120.0 (4)	C9—C10—C11	118.7 (3)
C3—C2—H2A	120.0	C9—C10—H10A	120.6
C1—C2—H2A	120.0	C11—C10—H10A	120.6
C4—C3—C2	118.4 (4)	C10—C11—C12	120.8 (3)
C4—C3—Cl1	119.7 (3)	C10—C11—C16	134.1 (3)
C2—C3—Cl1	121.8 (3)	C12—C11—C16	105.0 (3)
C3—C4—C5	120.7 (3)	C13—C12—N2	126.7 (3)
C3—C4—N1	128.4 (3)	C13—C12—C11	120.1 (3)
C5—C4—N1	110.9 (3)	N2—C12—C11	113.2 (2)
C6—C5—C4	121.6 (4)	C14—C13—C12	118.9 (3)
C6—C5—C7	131.6 (3)	C14—C13—Cl2	121.9 (2)
C4—C5—C7	106.8 (3)	C12—C13—Cl2	119.2 (2)
C1—C6—C5	117.9 (4)	C13—C14—C9	121.0 (3)
C1—C6—H6A	121.1	C13—C14—H14A	119.5
C5—C6—H6A	121.1	C9—C14—H14A	119.5
O1—C7—C5	131.5 (3)	O4—C15—N2	126.6 (3)
O1—C7—C8	123.4 (3)	O4—C15—C16	125.7 (3)
C5—C7—C8	105.0 (3)	N2—C15—C16	107.7 (3)
O2—C8—N1	128.3 (3)	O3—C16—C11	128.3 (3)
O2—C8—C7	125.5 (3)	O3—C16—C15	127.2 (3)
N1—C8—C7	106.2 (3)	C11—C16—C15	104.5 (3)

C6—C1—C2—C3	0.1 (6)	C14—C9—C10—C11	0.8 (5)
C1—C2—C3—C4	−0.7 (5)	C9—C10—C11—C12	−1.3 (4)
C1—C2—C3—Cl1	−178.2 (3)	C9—C10—C11—C16	−177.5 (3)
C2—C3—C4—C5	0.8 (5)	C15—N2—C12—C13	−176.5 (3)
Cl1—C3—C4—C5	178.4 (2)	C15—N2—C12—C11	1.6 (3)
C2—C3—C4—N1	−179.5 (3)	C10—C11—C12—C13	0.8 (4)
Cl1—C3—C4—N1	−1.9 (5)	C16—C11—C12—C13	178.0 (2)
C8—N1—C4—C3	178.8 (3)	C10—C11—C12—N2	−177.4 (2)
C8—N1—C4—C5	−1.5 (4)	C16—C11—C12—N2	−0.2 (3)
C3—C4—C5—C6	−0.4 (5)	N2—C12—C13—C14	178.0 (3)
N1—C4—C5—C6	179.8 (3)	C11—C12—C13—C14	0.1 (4)
C3—C4—C5—C7	−179.6 (3)	N2—C12—C13—Cl2	−1.0 (4)
N1—C4—C5—C7	0.6 (3)	C11—C12—C13—Cl2	−179.0 (2)
C2—C1—C6—C5	0.3 (6)	C12—C13—C14—C9	−0.6 (4)
C4—C5—C6—C1	−0.1 (5)	Cl2—C13—C14—C9	178.5 (2)
C7—C5—C6—C1	178.8 (3)	C10—C9—C14—C13	0.1 (5)
C6—C5—C7—O1	2.9 (6)	C12—N2—C15—O4	176.1 (3)
C4—C5—C7—O1	−178.1 (4)	C12—N2—C15—C16	−2.2 (3)
C6—C5—C7—C8	−178.7 (3)	C10—C11—C16—O3	−3.6 (6)
C4—C5—C7—C8	0.3 (3)	C12—C11—C16—O3	179.8 (3)
C4—N1—C8—O2	−178.7 (3)	C10—C11—C16—C15	175.6 (3)
C4—N1—C8—C7	1.6 (3)	C12—C11—C16—C15	−1.0 (3)
O1—C7—C8—O2	−2.3 (5)	O4—C15—C16—O3	2.9 (6)
C5—C7—C8—O2	179.1 (3)	N2—C15—C16—O3	−178.8 (3)
O1—C7—C8—N1	177.4 (3)	O4—C15—C16—C11	−176.3 (3)
C5—C7—C8—N1	−1.2 (3)	N2—C15—C16—C11	2.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.12	2.961 (4)	165
N2—H2B···O4ⁱ	0.86	2.10	2.923 (3)	160
C14—H14A···O2ⁱⁱ	0.93	2.46	3.385 (4)	172

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

Experimental details

Crystal data
Chemical formula	C₈H₄ClNO₂
M_r	181.57
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2450 (14), 8.6080 (17), 12.470 (3)
α, β, γ (°)	86.95 (3), 78.02 (3), 84.89 (3)
V (Å³)	757.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.876, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	2988, 2749, 2051
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.160, 1.01
No. of reflections	2749
No. of parameters	217
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.29

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software (Enraf–Nonius, 1989, XCAD4(Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.12	2.961 (4)	165
N2—H2B···O4ⁱ	0.86	2.10	2.923 (3)	160
C14—H14A···O2ⁱⁱ	0.93	2.46	3.385 (4)	172

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

Acknowledgements

The authors thank the Center of Testing and Analysis of Nanjing University for support.

References

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