7-Chloro-indoline-2,3-dione.

There are two mol-ecules in the asymmetric unit of the title compound, C(8)H(4)ClNO(2). In the crystal, they are linked by N-H⋯O hydrogen bonds, generating centrosymmetric, tetra-meric assemblies. A C-H⋯O inter-action 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 = 181.57

Triclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.160

S = 1.01

2749 reflections

217 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H4ClNO2	Z = 4
Mr = 181.57	F(000) = 368
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1P)2 + 0.250P] where P = (Fo2 + 2Fc2)/3
2749 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.63 e Å−3
13 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .