4-Chloro-1H-indole-2,3-dione

Juma, R.M.; Golen, J.A.; Manke, D.R.

doi:10.1107/S2414314616006891

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160689

doi:10.1107/S2414314616006891

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4-Chloro-1H-indole-2,3-dione

Rashid M. Juma,^a James A. Golen ^a and David R. Manke ^a ^*

^aDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA
^*Correspondence e-mail: dmanke@umassd.edu

Edited by J. Simpson, University of Otago, New Zealand (Received 16 April 2016; accepted 23 April 2016; online 29 April 2016)

The title compound, C₈H₄ClNO₂, has two planar molecules in the asymmetric unit, with the non-H atoms showing a mean deviation from planarity of 0.015 and 0.022 Å, respectively. In the crystal, the molecules are linked through N—H⋯O hydrogen bonds to form infinite chains along [010]. They are further connected through C—H⋯Cl close contacts with a donor–acceptor distance of 3.682 (5) Å. No π–π interactions are observed in the structure.

Keywords: crystal structure; hydrogen bonding; isatins.

CCDC reference: 1476174

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Chemical scheme

Structure description

As part of a continuing study of halogenated isatins, we report the crystal structure of 4-chloroisatin (4-chloro-1H-indole-2,3-dione), Fig. 1. The asymmetric unit of the structure contains two molecules that are nearly planar, with the non-H atoms possessing a mean deviation from planarity of 0.015 and 0.022 Å, respectively. The bond lengths and angles observed in the molecule are similar to those observed in the parent isatin (Goldschmidt & Llewellyn, 1950 ).

Figure 1
The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

In the crystal, molecules form infinite chains along [010] through N1—H1⋯O3 and N2—H2⋯O1 hydrogen bonds (Table 1). These chains are further linked through C5—H5⋯Cl2 close contacts (Fig. 2). Similar C—H⋯Cl close contacts were not observed in the other 4-chloroisatin structures that have been reported (Hughes & Fenical, 2010 ; Wang et al., 2012 ; Yu et al., 2012 ). Halogen–oxygen rather than C—H⋯halogen interactions are observed in the structures of 4-bromoisatin (Huang et al., 2016 ) and 4-iodoisatin (Golen & Manke, 2016 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.87 (1)	1.97 (2)	2.768 (5)	152 (4)
N2—H2⋯O1ⁱⁱ	0.87 (1)	2.11 (2)	2.905 (4)	152 (5)
C5—H5⋯Cl2ⁱⁱⁱ	0.95	2.91	3.682 (5)	139
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+2, y-{\script{3\over 2}}, -z+1]$ .

Figure 2
The molecular packing of the title compound viewed along the b axis, with hydrogen bonding shown as dashed lines.

Synthesis and crystallization

A commercial sample (Matrix Scientific) of 4-chloro-1H-indole-2,3-dione was used for crystallization. A sample suitable for single-crystal X-ray analysis was grown by slow evaporation from an acetone solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₈H₄ClNO₂
M_r	181.57
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	8.2745 (8), 6.0367 (6), 14.8609 (14)
β (°)	104.746 (5)
V (Å³)	717.86 (12)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.31
Crystal size (mm)	0.25 × 0.04 × 0.04

Data collection
Diffractometer	Bruker CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.205, 0.311
No. of measured, independent and observed [I > 2σ(I)] reflections	9961, 2579, 2388
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.04
No. of reflections	2579
No. of parameters	224
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.27
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	0.11 (3)
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1476174

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616006891/sj4026sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006891/sj4026Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006891/sj4026Isup3.cml

checkCIF report

Synthesis and crystallization top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Experimental top

Structure description top

As part of a continuing study of halogenated isatins, we report the crystal structure of 4-chloroisatin (4-chloro-1H-indole-2,3-dione), Fig.1. The asymmetric unit of the structure contains two molecules that are nearly planar, with the non-H atoms possessing a mean deviation from planarity of 0.015 and 0.022 Å, respectively. The bond lengths and angles observed in the molecule are similar to those observed in the parent isatin (Goldschmidt & Llewellyn, 1950).

In the crystal, molecules form infinite chains along [010] through N1—H1···O3 and N2—H2···O1 hydrogen bonds (Table 1). These chains are further linked through C5—H5···Cl2 close contacts (Fig. 2). Similar C—H···Cl close contacts were not observed in the other 4-chloroisatin structures that have been reported (Hughes & Fenical, 2010; Wang et al., 2012; Yu et al., 2012). Halogen–oxygen rather than C—H···halogen interactions are observed in the structures of 4-bromoisatin (Huang et al., 2016) and 4-iodoisatin (Golen & Manke, 2016).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The molecular packing of the title compound viewed along the b axis, with hydrogen bonding shown as dashed lines.

4-Chloro-1H-indole-2,3-dione top

Crystal data top

C₈H₄ClNO₂	F(000) = 368
M_r = 181.57	D_x = 1.680 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 6743 reflections
a = 8.2745 (8) Å	θ = 3.1–68.5°
b = 6.0367 (6) Å	µ = 4.31 mm⁻¹
c = 14.8609 (14) Å	T = 120 K
β = 104.746 (5)°	Block, orange
V = 717.86 (12) Å³	0.25 × 0.04 × 0.04 mm
Z = 4

Data collection top

Bruker CMOS diffractometer	2579 independent reflections
Radiation source: Cu	2388 reflections with I > 2σ(I)
HELIOS MX monochromator	R_int = 0.058
φ and ω scans	θ_max = 68.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −9→9
T_min = 0.205, T_max = 0.311	k = −7→7
9961 measured reflections	l = −17→17

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0531P)² + 0.171P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.58 e Å⁻³
2579 reflections	Δρ_min = −0.27 e Å⁻³
224 parameters	Absolute structure: Refined as an inversion twin.
3 restraints	Absolute structure parameter: 0.11 (3)

Crystal data top

C₈H₄ClNO₂	V = 717.86 (12) Å³
M_r = 181.57	Z = 4
Monoclinic, P2₁	Cu Kα radiation
a = 8.2745 (8) Å	µ = 4.31 mm⁻¹
b = 6.0367 (6) Å	T = 120 K
c = 14.8609 (14) Å	0.25 × 0.04 × 0.04 mm
β = 104.746 (5)°

Data collection top

Bruker CMOS diffractometer	2579 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2388 reflections with I > 2σ(I)
T_min = 0.205, T_max = 0.311	R_int = 0.058
9961 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.58 e Å⁻³
S = 1.04	Δρ_min = −0.27 e Å⁻³
2579 reflections	Absolute structure: Refined as an inversion twin.
224 parameters	Absolute structure parameter: 0.11 (3)
3 restraints

Special details top

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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Cl1	0.82671 (11)	−0.28031 (19)	0.40490 (7)	0.0329 (3)
Cl2	1.05021 (12)	1.19333 (19)	0.35368 (6)	0.0317 (3)
O1	0.2975 (4)	−0.0106 (5)	0.09037 (18)	0.0293 (7)
O2	0.5638 (3)	−0.2926 (6)	0.19884 (19)	0.0332 (7)
O3	1.1154 (3)	0.4626 (5)	0.11689 (18)	0.0279 (7)
O4	1.1901 (3)	0.7341 (6)	0.28454 (17)	0.0289 (7)
N1	0.3652 (4)	0.2002 (7)	0.2246 (2)	0.0246 (7)
H1	0.295 (5)	0.309 (6)	0.208 (3)	0.029*
N2	0.9124 (4)	0.7291 (7)	0.0657 (2)	0.0248 (8)
H2	0.868 (5)	0.688 (9)	0.0088 (14)	0.030*
C1	0.3785 (5)	0.0273 (7)	0.1694 (3)	0.0240 (9)
C2	0.5204 (5)	−0.1236 (7)	0.2281 (3)	0.0251 (9)
C3	0.5750 (5)	−0.0089 (7)	0.3177 (3)	0.0235 (9)
C4	0.6994 (5)	−0.0499 (8)	0.3987 (3)	0.0267 (9)
C5	0.7209 (5)	0.0939 (8)	0.4734 (3)	0.0285 (10)
H5	0.8050	0.0660	0.5290	0.034*
C6	0.6195 (5)	0.2785 (8)	0.4667 (3)	0.0285 (10)
H6	0.6340	0.3741	0.5189	0.034*
C7	0.4963 (5)	0.3293 (8)	0.3859 (3)	0.0281 (9)
H7	0.4289	0.4582	0.3815	0.034*
C8	0.4775 (4)	0.1828 (8)	0.3127 (2)	0.0226 (8)
C9	1.0412 (5)	0.6310 (7)	0.1266 (3)	0.0229 (9)
C10	1.0799 (5)	0.7769 (7)	0.2159 (3)	0.0221 (9)
C11	0.9586 (5)	0.9583 (7)	0.1941 (3)	0.0229 (9)
C12	0.9285 (5)	1.1431 (7)	0.2424 (3)	0.0252 (9)
C13	0.8008 (5)	1.2893 (8)	0.2018 (3)	0.0290 (10)
H13	0.7766	1.4130	0.2357	0.035*
C14	0.7089 (5)	1.2512 (8)	0.1105 (3)	0.0297 (10)
H14	0.6232	1.3527	0.0823	0.036*
C15	0.7387 (5)	1.0694 (8)	0.0594 (3)	0.0273 (10)
H15	0.6758	1.0467	−0.0029	0.033*
C16	0.8623 (5)	0.9235 (7)	0.1022 (3)	0.0237 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0260 (5)	0.0331 (6)	0.0362 (5)	0.0057 (5)	0.0014 (4)	0.0081 (5)
Cl2	0.0317 (5)	0.0347 (6)	0.0287 (5)	−0.0035 (5)	0.0076 (4)	−0.0071 (5)
O1	0.0320 (15)	0.0288 (18)	0.0237 (14)	0.0041 (13)	0.0010 (12)	−0.0016 (12)
O2	0.0370 (15)	0.0285 (18)	0.0328 (14)	0.0111 (17)	0.0064 (12)	−0.0021 (16)
O3	0.0281 (14)	0.0259 (17)	0.0290 (14)	0.0051 (14)	0.0061 (12)	0.0007 (13)
O4	0.0260 (13)	0.035 (2)	0.0231 (13)	0.0010 (15)	0.0006 (11)	0.0019 (14)
N1	0.0230 (16)	0.0250 (19)	0.0253 (15)	0.0065 (17)	0.0054 (12)	0.0030 (17)
N2	0.0238 (16)	0.026 (2)	0.0228 (15)	0.0023 (16)	0.0026 (12)	−0.0016 (15)
C1	0.023 (2)	0.023 (2)	0.027 (2)	0.0023 (17)	0.0082 (17)	0.0029 (17)
C2	0.022 (2)	0.025 (2)	0.029 (2)	0.0027 (17)	0.0095 (17)	0.0053 (18)
C3	0.0212 (19)	0.024 (2)	0.0264 (19)	−0.0024 (17)	0.0081 (15)	0.0050 (17)
C4	0.0191 (19)	0.031 (3)	0.030 (2)	−0.0020 (18)	0.0067 (16)	0.0081 (18)
C5	0.021 (2)	0.039 (3)	0.024 (2)	−0.0023 (19)	0.0034 (16)	0.0054 (18)
C6	0.030 (2)	0.035 (3)	0.0202 (19)	−0.0077 (19)	0.0056 (17)	−0.0027 (17)
C7	0.025 (2)	0.028 (3)	0.033 (2)	−0.0001 (18)	0.0099 (18)	0.0007 (18)
C8	0.0179 (17)	0.028 (2)	0.0219 (17)	−0.0005 (18)	0.0051 (14)	0.0031 (17)
C9	0.0207 (19)	0.025 (2)	0.0237 (19)	−0.0012 (17)	0.0078 (15)	0.0035 (16)
C10	0.0199 (19)	0.025 (2)	0.0226 (19)	−0.0002 (16)	0.0069 (16)	0.0037 (15)
C11	0.0214 (19)	0.025 (2)	0.0245 (18)	−0.0005 (17)	0.0098 (15)	0.0043 (17)
C12	0.0214 (19)	0.028 (3)	0.028 (2)	−0.0020 (17)	0.0099 (16)	0.0025 (17)
C13	0.029 (2)	0.024 (2)	0.039 (2)	0.0022 (17)	0.0165 (19)	0.0006 (18)
C14	0.0245 (19)	0.028 (3)	0.039 (2)	0.0070 (18)	0.0126 (17)	0.0083 (19)
C15	0.021 (2)	0.032 (3)	0.029 (2)	0.0031 (17)	0.0052 (17)	0.0057 (18)
C16	0.0213 (19)	0.027 (2)	0.0241 (19)	−0.0003 (17)	0.0076 (15)	0.0037 (17)

Geometric parameters (Å, º) top

Cl1—C4	1.733 (5)	C5—H5	0.9500
Cl2—C12	1.730 (4)	C5—C6	1.383 (7)
O1—C1	1.217 (5)	C6—H6	0.9500
O2—C2	1.200 (6)	C6—C7	1.398 (6)
O3—C9	1.215 (5)	C7—H7	0.9500
O4—C10	1.210 (5)	C7—C8	1.379 (6)
N1—H1	0.869 (7)	C9—C10	1.557 (6)
N1—C1	1.349 (6)	C10—C11	1.465 (6)
N1—C8	1.404 (4)	C11—C12	1.383 (6)
N2—H2	0.869 (7)	C11—C16	1.410 (6)
N2—C9	1.347 (5)	C12—C13	1.391 (6)
N2—C16	1.399 (6)	C13—H13	0.9500
C1—C2	1.564 (6)	C13—C14	1.395 (6)
C2—C3	1.467 (6)	C14—H14	0.9500
C3—C4	1.393 (6)	C14—C15	1.392 (6)
C3—C8	1.402 (6)	C15—H15	0.9500
C4—C5	1.385 (6)	C15—C16	1.376 (6)

C1—N1—H1	124 (3)	C3—C8—N1	110.3 (4)
C1—N1—C8	111.9 (4)	C7—C8—N1	127.1 (4)
C8—N1—H1	124 (3)	C7—C8—C3	122.7 (4)
C9—N2—H2	127 (4)	O3—C9—N2	128.7 (4)
C9—N2—C16	111.7 (3)	O3—C9—C10	125.0 (4)
C16—N2—H2	122 (4)	N2—C9—C10	106.3 (3)
O1—C1—N1	128.5 (4)	O4—C10—C9	123.0 (4)
O1—C1—C2	125.4 (4)	O4—C10—C11	132.3 (4)
N1—C1—C2	106.1 (3)	C11—C10—C9	104.7 (3)
O2—C2—C1	123.0 (4)	C12—C11—C10	133.8 (4)
O2—C2—C3	132.8 (4)	C12—C11—C16	119.4 (4)
C3—C2—C1	104.2 (3)	C16—C11—C10	106.9 (3)
C4—C3—C2	133.7 (4)	C11—C12—Cl2	120.0 (3)
C4—C3—C8	118.8 (4)	C11—C12—C13	120.3 (4)
C8—C3—C2	107.5 (3)	C13—C12—Cl2	119.7 (3)
C3—C4—Cl1	119.6 (3)	C12—C13—H13	120.6
C5—C4—Cl1	120.6 (3)	C12—C13—C14	118.9 (4)
C5—C4—C3	119.8 (4)	C14—C13—H13	120.6
C4—C5—H5	120.2	C13—C14—H14	118.9
C6—C5—C4	119.7 (4)	C15—C14—C13	122.1 (4)
C6—C5—H5	120.2	C15—C14—H14	118.9
C5—C6—H6	118.8	C14—C15—H15	121.1
C5—C6—C7	122.4 (4)	C16—C15—C14	117.8 (4)
C7—C6—H6	118.8	C16—C15—H15	121.1
C6—C7—H7	121.7	N2—C16—C11	110.5 (3)
C8—C7—C6	116.6 (4)	C15—C16—N2	128.0 (4)
C8—C7—H7	121.7	C15—C16—C11	121.5 (4)

Cl1—C4—C5—C6	179.2 (3)	C5—C6—C7—C8	1.4 (6)
Cl2—C12—C13—C14	177.2 (3)	C6—C7—C8—N1	−178.8 (4)
O1—C1—C2—O2	1.0 (7)	C6—C7—C8—C3	0.3 (6)
O1—C1—C2—C3	−178.8 (4)	C8—N1—C1—O1	178.1 (4)
O2—C2—C3—C4	2.8 (8)	C8—N1—C1—C2	−1.0 (4)
O2—C2—C3—C8	−179.3 (4)	C8—C3—C4—Cl1	−177.6 (3)
O3—C9—C10—O4	0.3 (6)	C8—C3—C4—C5	2.1 (6)
O3—C9—C10—C11	−179.9 (4)	C9—N2—C16—C11	−1.7 (4)
O4—C10—C11—C12	1.0 (8)	C9—N2—C16—C15	178.1 (4)
O4—C10—C11—C16	179.0 (4)	C9—C10—C11—C12	−178.7 (4)
N1—C1—C2—O2	−179.9 (4)	C9—C10—C11—C16	−0.8 (4)
N1—C1—C2—C3	0.3 (4)	C10—C11—C12—Cl2	0.0 (6)
N2—C9—C10—O4	−180.0 (4)	C10—C11—C12—C13	179.9 (4)
N2—C9—C10—C11	−0.2 (4)	C10—C11—C16—N2	1.5 (4)
C1—N1—C8—C3	1.3 (5)	C10—C11—C16—C15	−178.4 (4)
C1—N1—C8—C7	−179.6 (4)	C11—C12—C13—C14	−2.7 (6)
C1—C2—C3—C4	−177.4 (4)	C12—C11—C16—N2	179.8 (3)
C1—C2—C3—C8	0.4 (4)	C12—C11—C16—C15	0.0 (6)
C2—C3—C4—Cl1	0.0 (6)	C12—C13—C14—C15	1.3 (6)
C2—C3—C4—C5	179.7 (4)	C13—C14—C15—C16	0.7 (6)
C2—C3—C8—N1	−1.0 (4)	C14—C15—C16—N2	178.9 (4)
C2—C3—C8—C7	179.8 (4)	C14—C15—C16—C11	−1.3 (6)
C3—C4—C5—C6	−0.5 (6)	C16—N2—C9—O3	−179.2 (4)
C4—C3—C8—N1	177.2 (3)	C16—N2—C9—C10	1.1 (4)
C4—C3—C8—C7	−2.0 (6)	C16—C11—C12—Cl2	−177.8 (3)
C4—C5—C6—C7	−1.3 (6)	C16—C11—C12—C13	2.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.87 (1)	1.97 (2)	2.768 (5)	152 (4)
N2—H2···O1ⁱⁱ	0.87 (1)	2.11 (2)	2.905 (4)	152 (5)
C5—H5···Cl2ⁱⁱⁱ	0.95	2.91	3.682 (5)	139

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.869 (7)	1.97 (2)	2.768 (5)	152 (4)
N2—H2···O1ⁱⁱ	0.869 (7)	2.11 (2)	2.905 (4)	152 (5)
C5—H5···Cl2ⁱⁱⁱ	0.95	2.91	3.682 (5)	139.2

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

Experimental details

Crystal data
Chemical formula	C₈H₄ClNO₂
M_r	181.57
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	8.2745 (8), 6.0367 (6), 14.8609 (14)
β (°)	104.746 (5)
V (Å³)	717.86 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.31
Crystal size (mm)	0.25 × 0.04 × 0.04

Data collection
Diffractometer	Bruker CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2014)
T_min, T_max	0.205, 0.311
No. of measured, independent and observed [I > 2σ(I)] reflections	9961, 2579, 2388
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.04
No. of reflections	2579
No. of parameters	224
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.27
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	0.11 (3)

Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Acknowledgements

We greatly acknowledge support from the National Science Foundation (CHE-1429086).

References

Bruker (2014). APEX2, SAINT, and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Goldschmidt, G. H. & Llewellyn, F. J. (1950). Acta Cryst. 3, 294–305. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Golen, J. A. & Manke, D. R. (2016). IUCrData, 1, x160215. Google Scholar
Huang, H., Golen, J. A. & Manke, D. R. (2016). IUCrData, 1, x160007. Google Scholar
Hughes, C. C. & Fenical, W. (2010). J. Am. Chem. Soc. 132, 2528–2529. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wang, D. C., Leng, B. R., Wang, G. B., Wei, P. & Ou-yang, P. K. (2012). Acta Cryst. E68, o37. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, J. G., Tang, W., Wang, D. C. & Xu, H. (2012). Acta Cryst. E68, o219. Web of Science CSD CrossRef IUCr Journals Google Scholar

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IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160689

doi:10.1107/S2414314616006891

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Chloro-1H-indole-2,3-dione

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds