5,7-Dimethyl-1H-indole-2,3-dione

Perez, M.F.; Desikan, V.; Golen, J.A.; Manke, D.R.

doi:10.1107/S2414314617004448

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170444

https://doi.org/10.1107/S2414314617004448

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5,7-Dimethyl-1H-indole-2,3-dione

Matthew F. Perez,^a Vasumathi Desikan,^a James A. Golen ^b and David R. Manke ^b ^*

^aDepartment of Science & Math, Massasoit Community College, 1 Massasoit Boulevard, Brockton, MA 02302, USA, and ^bDepartment 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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 March 2017; accepted 20 March 2017; online 28 March 2017)

The title compound, C₁₀H₉NO₂, crystallizes with four molecules in the asymmetric unit. The molecules are all near planar, with the non-H atoms possessing mean deviations from planarity of 0.017, 0.026, 0.020 and 0.007 Å. In the crystal, the molecules form two dimers, each linked by a pair of N—H⋯O hydrogen bonds.

Keywords: crystal structure; isatins; N—H⋯O hydrogen bonds.

CCDC reference: 1539183

Structure description

Herein we report the crystal structure of 5,7-dimethyl-1H-indole-2,3-dione: there are four of these 5,7-dimethylisatin molecules in the asymmetric unit (Fig. 1). The molecules are near planar, with the non-H atoms demonstrating r.m.s. deviations of 0.017, 0.026, 0.020 and 0.007 Å. The bond lengths and angles of the title compound are consistent with those observed in the other reported 5,7-substituted isatin structure (Golen & Manke, 2016 ).

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

In the crystal, the four molecules combine into pairs, each linked through two N—H⋯O hydrogen bonds (Table 1). This dimerization is also observed in 7-methylisatin (Lyncee et al., 2017 ). The packing of the title compound, including hydrogen bonding, is shown in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86 (1)	2.07 (1)	2.903 (3)	164 (3)
N2—H2⋯O1	0.86 (1)	2.04 (1)	2.890 (3)	169 (3)
N3—H3⋯O7	0.86 (1)	2.09 (1)	2.922 (3)	163 (3)
N4—H4A⋯O5	0.86 (1)	2.02 (1)	2.867 (3)	168 (3)

Figure 2
The molecular packing of the title compound with hydrogen bonds drawn as dashed lines.

Synthesis and crystallization

A commercial sample (Acros) of 5,7-dimethyl-1H-indole-2,3-dione was used for the crystallization. A sample suitable for single-crystal X-ray analysis was grown from the slow evaporation of its methyl acetate solution.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₂
M_r	175.18
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	200
a, b, c (Å)	8.7148 (9), 13.5652 (17), 14.7832 (19)
α, β, γ (°)	91.562 (5), 96.341 (4), 103.776 (4)
V (Å³)	1684.4 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.4 × 0.4 × 0.04

Data collection
Diffractometer	Bruker D8 Venture
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.692, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	56302, 6187, 4523
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.189, 1.10
No. of reflections	6187
No. of parameters	489
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.27
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: 1539183

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617004448/hb4133sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617004448/hb4133Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617004448/hb4133Isup3.cml

checkCIF report

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).

5,7-Dimethyl-1H-indole-2,3-dione top

Crystal data top

C₁₀H₉NO₂	Z = 8
M_r = 175.18	F(000) = 736
Triclinic, P1	D_x = 1.382 Mg m⁻³
a = 8.7148 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5652 (17) Å	Cell parameters from 9884 reflections
c = 14.7832 (19) Å	θ = 3.1–25.3°
α = 91.562 (5)°	µ = 0.10 mm⁻¹
β = 96.341 (4)°	T = 200 K
γ = 103.776 (4)°	PLATE, orange
V = 1684.4 (4) Å³	0.4 × 0.4 × 0.04 mm

Data collection top

Bruker D8 Venture diffractometer	4523 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.060
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 25.4°, θ_min = 2.8°
T_min = 0.692, T_max = 0.745	h = −10→10
56302 measured reflections	k = −16→16
6187 independent reflections	l = −17→17

Refinement top

Refinement on F²	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.189	w = 1/[σ²(F_o²) + (0.0802P)² + 1.7614P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
6187 reflections	Δρ_max = 0.39 e Å⁻³
489 parameters	Δρ_min = −0.27 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
N1	0.4016 (2)	0.11027 (16)	0.69510 (15)	0.0238 (5)
H1	0.353 (3)	0.110 (2)	0.6412 (8)	0.029*
O1	0.6533 (2)	0.10964 (16)	0.66010 (14)	0.0363 (5)
O2	0.7175 (2)	0.10836 (17)	0.86028 (14)	0.0384 (5)
C1	0.5564 (3)	0.10994 (19)	0.71358 (19)	0.0251 (6)
C2	0.5897 (3)	0.10911 (19)	0.81955 (19)	0.0252 (6)
C3	0.4366 (3)	0.10900 (18)	0.85238 (18)	0.0232 (6)
C4	0.3923 (3)	0.10889 (19)	0.93965 (18)	0.0260 (6)
H4	0.4675	0.1094	0.9914	0.031*
C5	0.2352 (3)	0.10795 (19)	0.94964 (19)	0.0270 (6)
C6	0.1284 (3)	0.10665 (19)	0.87147 (19)	0.0271 (6)
H6	0.0214	0.1059	0.8792	0.033*
C7	0.1693 (3)	0.10639 (18)	0.78225 (18)	0.0237 (6)
C8	0.3269 (3)	0.10886 (18)	0.77573 (17)	0.0204 (5)
C9	0.1800 (4)	0.1088 (2)	1.0429 (2)	0.0368 (7)
H9A	0.2189	0.0584	1.0792	0.055*
H9B	0.0635	0.0921	1.0367	0.055*
H9C	0.2220	0.1765	1.0734	0.055*
C10	0.0509 (3)	0.1030 (2)	0.7002 (2)	0.0333 (7)
H10A	0.0857	0.1629	0.6652	0.050*
H10B	−0.0532	0.1026	0.7196	0.050*
H10C	0.0425	0.0413	0.6620	0.050*
N2	0.5531 (3)	0.12309 (17)	0.46883 (15)	0.0263 (5)
H2	0.595 (3)	0.119 (2)	0.5236 (8)	0.032*
O3	0.3010 (2)	0.12231 (16)	0.50270 (13)	0.0366 (5)
O4	0.2490 (2)	0.14359 (17)	0.30327 (15)	0.0412 (5)
C11	0.4008 (3)	0.1263 (2)	0.44925 (19)	0.0271 (6)
C12	0.3738 (3)	0.1373 (2)	0.34425 (19)	0.0274 (6)
C13	0.5289 (3)	0.14013 (19)	0.31343 (18)	0.0242 (6)
C14	0.5803 (3)	0.1514 (2)	0.22828 (19)	0.0274 (6)
H14	0.5083	0.1564	0.1764	0.033*
C15	0.7394 (3)	0.15539 (19)	0.21970 (19)	0.0281 (6)
C16	0.8409 (3)	0.14914 (19)	0.2986 (2)	0.0274 (6)
H16	0.9495	0.1528	0.2926	0.033*
C17	0.7926 (3)	0.13796 (19)	0.38523 (19)	0.0255 (6)
C18	0.6332 (3)	0.13328 (18)	0.39022 (18)	0.0238 (6)
C19	0.8017 (4)	0.1678 (2)	0.1285 (2)	0.0389 (7)
H19A	0.7569	0.1056	0.0897	0.058*
H19B	0.9180	0.1805	0.1372	0.058*
H19C	0.7707	0.2253	0.0994	0.058*
C20	0.9053 (3)	0.1327 (2)	0.4685 (2)	0.0354 (7)
H20A	0.9159	0.1924	0.5097	0.053*
H20B	1.0097	0.1314	0.4504	0.053*
H20C	0.8638	0.0708	0.4996	0.053*
N3	0.3688 (2)	0.35893 (17)	0.85114 (15)	0.0238 (5)
H3	0.318 (3)	0.344 (2)	0.7975 (9)	0.029*
O5	0.6154 (2)	0.34703 (15)	0.81535 (13)	0.0318 (5)
O6	0.6912 (2)	0.37267 (16)	1.01601 (14)	0.0358 (5)
C21	0.5233 (3)	0.35717 (19)	0.86965 (18)	0.0243 (6)
C22	0.5623 (3)	0.36974 (19)	0.97550 (18)	0.0248 (6)
C23	0.4129 (3)	0.37657 (18)	1.00930 (17)	0.0225 (5)
C24	0.3723 (3)	0.3857 (2)	1.09591 (18)	0.0270 (6)
H24	0.4497	0.3905	1.1475	0.032*
C25	0.2169 (3)	0.3880 (2)	1.10712 (19)	0.0286 (6)
C26	0.1068 (3)	0.3803 (2)	1.02911 (19)	0.0278 (6)
H26	0.0009	0.3825	1.0371	0.033*
C27	0.1434 (3)	0.36965 (19)	0.94057 (18)	0.0245 (6)
C28	0.3001 (3)	0.36819 (18)	0.93224 (17)	0.0216 (5)
C29	0.1678 (4)	0.3968 (3)	1.2013 (2)	0.0401 (7)
H29A	0.1848	0.3388	1.2356	0.060*
H29B	0.0549	0.3974	1.1962	0.060*
H29C	0.2318	0.4600	1.2331	0.060*
C30	0.0199 (3)	0.3593 (2)	0.8587 (2)	0.0361 (7)
H30A	0.0486	0.4179	0.8213	0.054*
H30B	−0.0843	0.3565	0.8791	0.054*
H30C	0.0151	0.2967	0.8226	0.054*
N4	0.5103 (2)	0.35401 (17)	0.62544 (15)	0.0252 (5)
H4A	0.554 (3)	0.350 (2)	0.6800 (8)	0.030*
O7	0.2527 (2)	0.34008 (15)	0.65678 (13)	0.0339 (5)
O8	0.2033 (2)	0.37014 (16)	0.45880 (14)	0.0369 (5)
C31	0.3544 (3)	0.35165 (19)	0.60458 (18)	0.0256 (6)
C32	0.3291 (3)	0.36678 (19)	0.50041 (18)	0.0255 (6)
C33	0.4871 (3)	0.37722 (18)	0.47077 (17)	0.0221 (5)
C34	0.5404 (3)	0.39321 (19)	0.38603 (18)	0.0255 (6)
H34	0.4687	0.3990	0.3342	0.031*
C35	0.7010 (3)	0.40072 (19)	0.37810 (18)	0.0260 (6)
C36	0.8016 (3)	0.39118 (19)	0.45634 (19)	0.0280 (6)
H36	0.9104	0.3955	0.4506	0.034*
C37	0.7510 (3)	0.37566 (19)	0.54253 (18)	0.0240 (6)
C38	0.5905 (3)	0.36892 (18)	0.54667 (17)	0.0219 (5)
C39	0.7648 (4)	0.4188 (2)	0.2880 (2)	0.0372 (7)
H39A	0.7093	0.3631	0.2438	0.056*
H39B	0.8789	0.4217	0.2956	0.056*
H39C	0.7476	0.4832	0.2659	0.056*
C40	0.8614 (3)	0.3659 (2)	0.6257 (2)	0.0349 (7)
H40A	0.8644	0.4202	0.6714	0.052*
H40B	0.9686	0.3713	0.6088	0.052*
H40C	0.8232	0.2997	0.6511	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0199 (11)	0.0291 (12)	0.0230 (12)	0.0071 (9)	0.0016 (9)	0.0024 (9)
O1	0.0239 (10)	0.0527 (13)	0.0358 (12)	0.0127 (9)	0.0098 (9)	0.0065 (9)
O2	0.0222 (11)	0.0554 (13)	0.0399 (12)	0.0146 (9)	0.0006 (9)	0.0065 (10)
C1	0.0161 (13)	0.0262 (13)	0.0350 (15)	0.0072 (10)	0.0069 (11)	0.0036 (11)
C2	0.0190 (13)	0.0238 (13)	0.0333 (15)	0.0062 (10)	0.0025 (11)	0.0033 (11)
C3	0.0191 (13)	0.0195 (12)	0.0311 (15)	0.0053 (9)	0.0019 (10)	0.0020 (10)
C4	0.0229 (14)	0.0271 (14)	0.0283 (15)	0.0065 (10)	0.0026 (11)	0.0047 (11)
C5	0.0260 (14)	0.0231 (13)	0.0329 (15)	0.0052 (10)	0.0092 (11)	0.0031 (11)
C6	0.0197 (13)	0.0251 (13)	0.0384 (16)	0.0058 (10)	0.0101 (11)	0.0043 (11)
C7	0.0172 (12)	0.0196 (12)	0.0341 (15)	0.0036 (9)	0.0042 (10)	0.0020 (10)
C8	0.0185 (12)	0.0182 (12)	0.0245 (13)	0.0038 (9)	0.0046 (10)	0.0027 (10)
C9	0.0326 (16)	0.0420 (17)	0.0375 (17)	0.0072 (13)	0.0150 (13)	0.0051 (13)
C10	0.0191 (14)	0.0399 (16)	0.0407 (17)	0.0080 (11)	0.0005 (12)	0.0041 (13)
N2	0.0188 (11)	0.0338 (12)	0.0268 (12)	0.0075 (9)	0.0019 (9)	0.0012 (10)
O3	0.0230 (10)	0.0578 (14)	0.0319 (11)	0.0126 (9)	0.0094 (9)	0.0029 (10)
O4	0.0188 (10)	0.0629 (15)	0.0436 (13)	0.0160 (9)	−0.0017 (9)	0.0034 (11)
C11	0.0201 (13)	0.0289 (14)	0.0321 (15)	0.0060 (10)	0.0033 (11)	−0.0015 (11)
C12	0.0193 (14)	0.0300 (14)	0.0333 (15)	0.0072 (10)	0.0028 (11)	0.0001 (11)
C13	0.0187 (13)	0.0225 (13)	0.0311 (15)	0.0057 (10)	0.0007 (11)	−0.0017 (11)
C14	0.0236 (14)	0.0279 (14)	0.0305 (15)	0.0067 (10)	0.0027 (11)	0.0013 (11)
C15	0.0274 (14)	0.0204 (13)	0.0372 (16)	0.0051 (10)	0.0088 (12)	0.0002 (11)
C16	0.0187 (13)	0.0245 (13)	0.0407 (16)	0.0061 (10)	0.0085 (11)	0.0013 (11)
C17	0.0184 (13)	0.0204 (13)	0.0376 (16)	0.0051 (10)	0.0031 (11)	−0.0015 (11)
C18	0.0185 (13)	0.0200 (12)	0.0336 (15)	0.0059 (9)	0.0030 (11)	−0.0002 (10)
C19	0.0359 (17)	0.0427 (17)	0.0395 (18)	0.0075 (13)	0.0145 (14)	0.0045 (14)
C20	0.0220 (14)	0.0430 (17)	0.0413 (18)	0.0106 (12)	−0.0015 (12)	−0.0007 (13)
N3	0.0190 (11)	0.0321 (12)	0.0207 (11)	0.0063 (9)	0.0044 (9)	0.0020 (9)
O5	0.0221 (10)	0.0433 (12)	0.0323 (11)	0.0099 (8)	0.0086 (8)	0.0037 (9)
O6	0.0199 (10)	0.0514 (13)	0.0364 (12)	0.0112 (9)	−0.0012 (8)	0.0056 (9)
C21	0.0212 (13)	0.0256 (13)	0.0267 (14)	0.0056 (10)	0.0042 (11)	0.0042 (10)
C22	0.0209 (14)	0.0249 (13)	0.0287 (14)	0.0057 (10)	0.0028 (11)	0.0056 (11)
C23	0.0178 (12)	0.0231 (13)	0.0256 (14)	0.0039 (10)	0.0013 (10)	−0.0002 (10)
C24	0.0235 (14)	0.0312 (14)	0.0258 (14)	0.0057 (11)	0.0031 (11)	−0.0007 (11)
C25	0.0264 (14)	0.0322 (15)	0.0293 (15)	0.0085 (11)	0.0088 (11)	0.0016 (11)
C26	0.0211 (13)	0.0303 (14)	0.0337 (15)	0.0074 (10)	0.0078 (11)	0.0042 (11)
C27	0.0166 (13)	0.0274 (14)	0.0306 (15)	0.0067 (10)	0.0032 (10)	0.0042 (11)
C28	0.0196 (12)	0.0213 (12)	0.0246 (13)	0.0051 (9)	0.0046 (10)	0.0024 (10)
C29	0.0326 (16)	0.058 (2)	0.0316 (17)	0.0118 (14)	0.0108 (13)	−0.0025 (14)
C30	0.0191 (14)	0.0547 (19)	0.0364 (17)	0.0132 (12)	0.0008 (12)	0.0108 (14)
N4	0.0198 (11)	0.0353 (12)	0.0233 (12)	0.0101 (9)	0.0056 (9)	0.0059 (10)
O7	0.0240 (10)	0.0474 (12)	0.0331 (11)	0.0106 (8)	0.0112 (8)	0.0061 (9)
O8	0.0200 (10)	0.0542 (13)	0.0386 (12)	0.0135 (9)	0.0015 (9)	0.0056 (10)
C31	0.0205 (13)	0.0285 (14)	0.0300 (15)	0.0090 (10)	0.0055 (11)	0.0050 (11)
C32	0.0191 (13)	0.0273 (14)	0.0306 (15)	0.0063 (10)	0.0035 (11)	0.0035 (11)
C33	0.0178 (13)	0.0239 (13)	0.0257 (14)	0.0068 (10)	0.0033 (10)	0.0016 (10)
C34	0.0244 (14)	0.0293 (14)	0.0221 (13)	0.0061 (10)	0.0009 (10)	−0.0013 (10)
C35	0.0238 (14)	0.0250 (13)	0.0299 (15)	0.0047 (10)	0.0088 (11)	0.0007 (11)
C36	0.0195 (13)	0.0260 (14)	0.0387 (16)	0.0050 (10)	0.0062 (11)	−0.0021 (11)
C37	0.0171 (12)	0.0234 (13)	0.0319 (15)	0.0065 (10)	0.0015 (10)	−0.0010 (11)
C38	0.0199 (13)	0.0204 (12)	0.0263 (14)	0.0056 (9)	0.0045 (10)	0.0016 (10)
C39	0.0380 (17)	0.0395 (17)	0.0359 (17)	0.0082 (13)	0.0155 (13)	0.0006 (13)
C40	0.0199 (14)	0.0480 (18)	0.0370 (17)	0.0113 (12)	−0.0006 (12)	−0.0044 (13)

Geometric parameters (Å, º) top

N1—H1	0.860 (5)	N3—H3	0.860 (5)
N1—C1	1.348 (3)	N3—C21	1.350 (3)
N1—C8	1.418 (3)	N3—C28	1.413 (3)
O1—C1	1.219 (3)	O5—C21	1.223 (3)
O2—C2	1.209 (3)	O6—C22	1.204 (3)
C1—C2	1.562 (4)	C21—C22	1.560 (4)
C2—C3	1.469 (3)	C22—C23	1.467 (3)
C3—C4	1.387 (4)	C23—C24	1.375 (4)
C3—C8	1.399 (4)	C23—C28	1.403 (3)
C4—H4	0.9500	C24—H24	0.9500
C4—C5	1.390 (4)	C24—C25	1.390 (4)
C5—C6	1.398 (4)	C25—C26	1.401 (4)
C5—C9	1.510 (4)	C25—C29	1.511 (4)
C6—H6	0.9500	C26—H26	0.9500
C6—C7	1.404 (4)	C26—C27	1.393 (4)
C7—C8	1.380 (3)	C27—C28	1.389 (3)
C7—C10	1.496 (4)	C27—C30	1.508 (4)
C9—H9A	0.9800	C29—H29A	0.9800
C9—H9B	0.9800	C29—H29B	0.9800
C9—H9C	0.9800	C29—H29C	0.9800
C10—H10A	0.9800	C30—H30A	0.9800
C10—H10B	0.9800	C30—H30B	0.9800
C10—H10C	0.9800	C30—H30C	0.9800
N2—H2	0.860 (5)	N4—H4A	0.862 (5)
N2—C11	1.338 (3)	N4—C31	1.352 (3)
N2—C18	1.414 (3)	N4—C38	1.418 (3)
O3—C11	1.231 (3)	O7—C31	1.223 (3)
O4—C12	1.208 (3)	O8—C32	1.207 (3)
C11—C12	1.561 (4)	C31—C32	1.558 (4)
C12—C13	1.465 (4)	C32—C33	1.467 (3)
C13—C14	1.382 (4)	C33—C34	1.388 (4)
C13—C18	1.394 (4)	C33—C38	1.384 (4)
C14—H14	0.9500	C34—H34	0.9500
C14—C15	1.395 (4)	C34—C35	1.398 (4)
C15—C16	1.401 (4)	C35—C36	1.401 (4)
C15—C19	1.507 (4)	C35—C39	1.503 (4)
C16—H16	0.9500	C36—H36	0.9500
C16—C17	1.393 (4)	C36—C37	1.399 (4)
C17—C18	1.386 (3)	C37—C38	1.388 (3)
C17—C20	1.502 (4)	C37—C40	1.505 (4)
C19—H19A	0.9800	C39—H39A	0.9800
C19—H19B	0.9800	C39—H39B	0.9800
C19—H19C	0.9800	C39—H39C	0.9800
C20—H20A	0.9800	C40—H40A	0.9800
C20—H20B	0.9800	C40—H40B	0.9800
C20—H20C	0.9800	C40—H40C	0.9800

C1—N1—H1	125 (2)	C21—N3—H3	122.3 (19)
C1—N1—C8	111.6 (2)	C21—N3—C28	111.0 (2)
C8—N1—H1	124 (2)	C28—N3—H3	126 (2)
N1—C1—C2	106.0 (2)	N3—C21—C22	106.2 (2)
O1—C1—N1	128.3 (3)	O5—C21—N3	127.6 (2)
O1—C1—C2	125.7 (2)	O5—C21—C22	126.2 (2)
O2—C2—C1	124.1 (2)	O6—C22—C21	124.2 (2)
O2—C2—C3	131.1 (3)	O6—C22—C23	130.6 (3)
C3—C2—C1	104.8 (2)	C23—C22—C21	105.2 (2)
C4—C3—C2	131.6 (2)	C24—C23—C22	132.2 (2)
C4—C3—C8	121.2 (2)	C24—C23—C28	121.3 (2)
C8—C3—C2	107.2 (2)	C28—C23—C22	106.4 (2)
C3—C4—H4	120.8	C23—C24—H24	120.4
C3—C4—C5	118.5 (2)	C23—C24—C25	119.2 (2)
C5—C4—H4	120.8	C25—C24—H24	120.4
C4—C5—C6	118.7 (2)	C24—C25—C26	118.4 (2)
C4—C5—C9	121.0 (3)	C24—C25—C29	120.6 (3)
C6—C5—C9	120.3 (2)	C26—C25—C29	121.0 (2)
C5—C6—H6	117.9	C25—C26—H26	118.1
C5—C6—C7	124.2 (2)	C27—C26—C25	123.8 (2)
C7—C6—H6	117.9	C27—C26—H26	118.1
C6—C7—C10	122.6 (2)	C26—C27—C30	122.0 (2)
C8—C7—C6	115.0 (2)	C28—C27—C26	116.0 (2)
C8—C7—C10	122.4 (2)	C28—C27—C30	122.0 (2)
C3—C8—N1	110.3 (2)	C23—C28—N3	111.1 (2)
C7—C8—N1	127.3 (2)	C27—C28—N3	127.7 (2)
C7—C8—C3	122.3 (2)	C27—C28—C23	121.2 (2)
C5—C9—H9A	109.5	C25—C29—H29A	109.5
C5—C9—H9B	109.5	C25—C29—H29B	109.5
C5—C9—H9C	109.5	C25—C29—H29C	109.5
H9A—C9—H9B	109.5	H29A—C29—H29B	109.5
H9A—C9—H9C	109.5	H29A—C29—H29C	109.5
H9B—C9—H9C	109.5	H29B—C29—H29C	109.5
C7—C10—H10A	109.5	C27—C30—H30A	109.5
C7—C10—H10B	109.5	C27—C30—H30B	109.5
C7—C10—H10C	109.5	C27—C30—H30C	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C11—N2—H2	122 (2)	C31—N4—H4A	123 (2)
C11—N2—C18	111.5 (2)	C31—N4—C38	110.7 (2)
C18—N2—H2	126 (2)	C38—N4—H4A	126 (2)
N2—C11—C12	106.3 (2)	N4—C31—C32	106.4 (2)
O3—C11—N2	127.5 (3)	O7—C31—N4	127.1 (3)
O3—C11—C12	126.2 (2)	O7—C31—C32	126.5 (2)
O4—C12—C11	124.1 (2)	O8—C32—C31	124.3 (2)
O4—C12—C13	131.4 (3)	O8—C32—C33	131.2 (3)
C13—C12—C11	104.5 (2)	C33—C32—C31	104.5 (2)
C14—C13—C12	131.6 (2)	C34—C33—C32	131.6 (2)
C14—C13—C18	121.1 (2)	C38—C33—C32	107.4 (2)
C18—C13—C12	107.2 (2)	C38—C33—C34	121.0 (2)
C13—C14—H14	120.5	C33—C34—H34	120.5
C13—C14—C15	119.0 (3)	C33—C34—C35	119.0 (2)
C15—C14—H14	120.5	C35—C34—H34	120.5
C14—C15—C16	118.2 (3)	C34—C35—C36	118.3 (2)
C14—C15—C19	121.1 (3)	C34—C35—C39	121.0 (3)
C16—C15—C19	120.7 (2)	C36—C35—C39	120.7 (2)
C15—C16—H16	117.9	C35—C36—H36	118.1
C17—C16—C15	124.1 (2)	C37—C36—C35	123.8 (2)
C17—C16—H16	117.9	C37—C36—H36	118.1
C16—C17—C20	122.7 (2)	C36—C37—C40	122.8 (2)
C18—C17—C16	115.6 (2)	C38—C37—C36	115.6 (2)
C18—C17—C20	121.7 (3)	C38—C37—C40	121.6 (2)
C13—C18—N2	110.5 (2)	C33—C38—N4	111.0 (2)
C17—C18—N2	127.6 (2)	C33—C38—C37	122.4 (2)
C17—C18—C13	121.9 (2)	C37—C38—N4	126.6 (2)
C15—C19—H19A	109.5	C35—C39—H39A	109.5
C15—C19—H19B	109.5	C35—C39—H39B	109.5
C15—C19—H19C	109.5	C35—C39—H39C	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
C17—C20—H20A	109.5	C37—C40—H40A	109.5
C17—C20—H20B	109.5	C37—C40—H40B	109.5
C17—C20—H20C	109.5	C37—C40—H40C	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5

N1—C1—C2—O2	179.8 (2)	N3—C21—C22—O6	−179.1 (2)
N1—C1—C2—C3	0.0 (3)	N3—C21—C22—C23	0.8 (3)
O1—C1—C2—O2	0.2 (4)	O5—C21—C22—O6	1.4 (4)
O1—C1—C2—C3	−179.5 (3)	O5—C21—C22—C23	−178.7 (2)
O2—C2—C3—C4	0.6 (5)	O6—C22—C23—C24	−1.8 (5)
O2—C2—C3—C8	−179.3 (3)	O6—C22—C23—C28	−179.7 (3)
C1—N1—C8—C3	0.8 (3)	C21—N3—C28—C23	2.1 (3)
C1—N1—C8—C7	−178.4 (2)	C21—N3—C28—C27	−178.0 (2)
C1—C2—C3—C4	−179.6 (3)	C21—C22—C23—C24	178.2 (3)
C1—C2—C3—C8	0.5 (3)	C21—C22—C23—C28	0.4 (3)
C2—C3—C4—C5	−179.5 (2)	C22—C23—C24—C25	−178.4 (3)
C2—C3—C8—N1	−0.8 (3)	C22—C23—C28—N3	−1.4 (3)
C2—C3—C8—C7	178.5 (2)	C22—C23—C28—C27	178.7 (2)
C3—C4—C5—C6	0.3 (4)	C23—C24—C25—C26	0.2 (4)
C3—C4—C5—C9	−179.4 (2)	C23—C24—C25—C29	179.4 (3)
C4—C3—C8—N1	179.3 (2)	C24—C23—C28—N3	−179.6 (2)
C4—C3—C8—C7	−1.4 (4)	C24—C23—C28—C27	0.5 (4)
C4—C5—C6—C7	−0.1 (4)	C24—C25—C26—C27	0.6 (4)
C5—C6—C7—C8	−0.8 (4)	C25—C26—C27—C28	−0.9 (4)
C5—C6—C7—C10	178.8 (2)	C25—C26—C27—C30	178.6 (3)
C6—C7—C8—N1	−179.3 (2)	C26—C27—C28—N3	−179.6 (2)
C6—C7—C8—C3	1.6 (3)	C26—C27—C28—C23	0.3 (4)
C8—N1—C1—O1	179.0 (3)	C28—N3—C21—O5	177.8 (3)
C8—N1—C1—C2	−0.5 (3)	C28—N3—C21—C22	−1.7 (3)
C8—C3—C4—C5	0.4 (4)	C28—C23—C24—C25	−0.8 (4)
C9—C5—C6—C7	179.6 (2)	C29—C25—C26—C27	−178.5 (3)
C10—C7—C8—N1	1.1 (4)	C30—C27—C28—N3	1.0 (4)
C10—C7—C8—C3	−178.1 (2)	C30—C27—C28—C23	−179.1 (2)
N2—C11—C12—O4	−179.2 (3)	N4—C31—C32—O8	−178.9 (3)
N2—C11—C12—C13	−0.4 (3)	N4—C31—C32—C33	−0.1 (3)
O3—C11—C12—O4	0.2 (4)	O7—C31—C32—O8	1.0 (4)
O3—C11—C12—C13	179.0 (3)	O7—C31—C32—C33	179.8 (3)
O4—C12—C13—C14	0.5 (5)	O8—C32—C33—C34	−0.7 (5)
O4—C12—C13—C18	177.8 (3)	O8—C32—C33—C38	178.9 (3)
C11—N2—C18—C13	−2.1 (3)	C31—N4—C38—C33	0.2 (3)
C11—N2—C18—C17	176.9 (2)	C31—N4—C38—C37	179.7 (2)
C11—C12—C13—C14	−178.2 (3)	C31—C32—C33—C34	−179.3 (3)
C11—C12—C13—C18	−0.8 (3)	C31—C32—C33—C38	0.2 (3)
C12—C13—C14—C15	177.4 (3)	C32—C33—C34—C35	179.6 (2)
C12—C13—C18—N2	1.8 (3)	C32—C33—C38—N4	−0.3 (3)
C12—C13—C18—C17	−177.3 (2)	C32—C33—C38—C37	−179.8 (2)
C13—C14—C15—C16	−0.9 (4)	C33—C34—C35—C36	0.3 (4)
C13—C14—C15—C19	−179.9 (2)	C33—C34—C35—C39	−179.6 (2)
C14—C13—C18—N2	179.5 (2)	C34—C33—C38—N4	179.3 (2)
C14—C13—C18—C17	0.4 (4)	C34—C33—C38—C37	−0.2 (4)
C14—C15—C16—C17	0.8 (4)	C34—C35—C36—C37	−0.8 (4)
C15—C16—C17—C18	−0.1 (4)	C35—C36—C37—C38	0.7 (4)
C15—C16—C17—C20	−179.3 (2)	C35—C36—C37—C40	−179.9 (2)
C16—C17—C18—N2	−179.4 (2)	C36—C37—C38—N4	−179.6 (2)
C16—C17—C18—C13	−0.5 (4)	C36—C37—C38—C33	−0.2 (4)
C18—N2—C11—O3	−177.9 (3)	C38—N4—C31—O7	−180.0 (3)
C18—N2—C11—C12	1.5 (3)	C38—N4—C31—C32	0.0 (3)
C18—C13—C14—C15	0.3 (4)	C38—C33—C34—C35	0.1 (4)
C19—C15—C16—C17	179.8 (2)	C39—C35—C36—C37	179.1 (2)
C20—C17—C18—N2	−0.2 (4)	C40—C37—C38—N4	0.9 (4)
C20—C17—C18—C13	178.7 (2)	C40—C37—C38—C33	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86 (1)	2.07 (1)	2.903 (3)	164 (3)
N2—H2···O1	0.86 (1)	2.04 (1)	2.890 (3)	169 (3)
N3—H3···O7	0.86 (1)	2.09 (1)	2.922 (3)	163 (3)
N4—H4A···O5	0.86 (1)	2.02 (1)	2.867 (3)	168 (3)

Funding information

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. CHE-1429086); Massachusetts Clean Energy Center.

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
Golen, J. A. & Manke, D. R. (2016). IUCrData, 1, x161510. Google Scholar
Lyncee, M. A., Desikan, V., Golen, J. A. & Manke, D. R. (2017). IUCrData, 2, x170378. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170444

https://doi.org/10.1107/S2414314617004448

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

5,7-Di­methyl-1H-indole-2,3-dione

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

5,7-Dimethyl-1H-indole-2,3-dione