7-Chloro­indoline-2,3-dione

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.160
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.16
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          5
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C7     -   C8     ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C15    -   C16    ...       1.55 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

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

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


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

---

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).

S1. Experimental

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).

S2. Refinement

H atoms were positioned geometrically, with N—H = 0.86Å and C—H = 0.93Å and refined as riding with U_iso(H) = xU_eq(C,O,N), where x = 1.5 for NH H and x = 1.2 for all other H atoms.

Computing details

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

	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

Crystal data

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) Å^3	0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2051 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Graphite monochromator	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

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.250P] where P = (Fo^2 + 2Fc^2)/3
2749 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.63 e Å^−3
13 restraints	Δρmin = −0.29 e Å^−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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4^i	0.86	2.12	2.961 (4)	165
N2—H2B···O4^i	0.86	2.10	2.923 (3)	160
C14—H14A···O2^ii	0.93	2.46	3.385 (4)	172

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