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

Journal logoIUCrDATA
ISSN: 2414-3146

5,7-Di­methyl-1H-indole-2,3-dione

CROSSMARK_Color_square_no_text.svg

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[link]). 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[Golen, J. A. & Manke, D. R. (2016). IUCrData, 1, x161510.]).

[Figure 1]
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[link]). This dimerization is also observed in 7-methyl­isatin (Lyncee et al., 2017[Lyncee, M. A., Desikan, V., Golen, J. A. & Manke, D. R. (2017). IUCrData, 2, x170378.]). The packing of the title compound, including hydrogen bonding, is shown in Fig. 2[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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]
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[link].

Table 2
Experimental details

Crystal data
Chemical formula C10H9NO2
Mr 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)
V3) 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[Bruker (2014). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.692, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections 56302, 6187, 4523
Rint 0.060
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.39, −0.27
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


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
C10H9NO2Z = 8
Mr = 175.18F(000) = 736
Triclinic, P1Dx = 1.382 Mg m3
a = 8.7148 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.5652 (17) ÅCell parameters from 9884 reflections
c = 14.7832 (19) Åθ = 3.1–25.3°
α = 91.562 (5)°µ = 0.10 mm1
β = 96.341 (4)°T = 200 K
γ = 103.776 (4)°PLATE, orange
V = 1684.4 (4) Å30.4 × 0.4 × 0.04 mm
Data collection top
Bruker D8 Venture
diffractometer
4523 reflections with I > 2σ(I)
φ and ω scansRint = 0.060
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 25.4°, θmin = 2.8°
Tmin = 0.692, Tmax = 0.745h = 1010
56302 measured reflectionsk = 1616
6187 independent reflectionsl = 1717
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189 w = 1/[σ2(Fo2) + (0.0802P)2 + 1.7614P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
6187 reflectionsΔρmax = 0.39 e Å3
489 parametersΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
N10.4016 (2)0.11027 (16)0.69510 (15)0.0238 (5)
H10.353 (3)0.110 (2)0.6412 (8)0.029*
O10.6533 (2)0.10964 (16)0.66010 (14)0.0363 (5)
O20.7175 (2)0.10836 (17)0.86028 (14)0.0384 (5)
C10.5564 (3)0.10994 (19)0.71358 (19)0.0251 (6)
C20.5897 (3)0.10911 (19)0.81955 (19)0.0252 (6)
C30.4366 (3)0.10900 (18)0.85238 (18)0.0232 (6)
C40.3923 (3)0.10889 (19)0.93965 (18)0.0260 (6)
H40.46750.10940.99140.031*
C50.2352 (3)0.10795 (19)0.94964 (19)0.0270 (6)
C60.1284 (3)0.10665 (19)0.87147 (19)0.0271 (6)
H60.02140.10590.87920.033*
C70.1693 (3)0.10639 (18)0.78225 (18)0.0237 (6)
C80.3269 (3)0.10886 (18)0.77573 (17)0.0204 (5)
C90.1800 (4)0.1088 (2)1.0429 (2)0.0368 (7)
H9A0.21890.05841.07920.055*
H9B0.06350.09211.03670.055*
H9C0.22200.17651.07340.055*
C100.0509 (3)0.1030 (2)0.7002 (2)0.0333 (7)
H10A0.08570.16290.66520.050*
H10B0.05320.10260.71960.050*
H10C0.04250.04130.66200.050*
N20.5531 (3)0.12309 (17)0.46883 (15)0.0263 (5)
H20.595 (3)0.119 (2)0.5236 (8)0.032*
O30.3010 (2)0.12231 (16)0.50270 (13)0.0366 (5)
O40.2490 (2)0.14359 (17)0.30327 (15)0.0412 (5)
C110.4008 (3)0.1263 (2)0.44925 (19)0.0271 (6)
C120.3738 (3)0.1373 (2)0.34425 (19)0.0274 (6)
C130.5289 (3)0.14013 (19)0.31343 (18)0.0242 (6)
C140.5803 (3)0.1514 (2)0.22828 (19)0.0274 (6)
H140.50830.15640.17640.033*
C150.7394 (3)0.15539 (19)0.21970 (19)0.0281 (6)
C160.8409 (3)0.14914 (19)0.2986 (2)0.0274 (6)
H160.94950.15280.29260.033*
C170.7926 (3)0.13796 (19)0.38523 (19)0.0255 (6)
C180.6332 (3)0.13328 (18)0.39022 (18)0.0238 (6)
C190.8017 (4)0.1678 (2)0.1285 (2)0.0389 (7)
H19A0.75690.10560.08970.058*
H19B0.91800.18050.13720.058*
H19C0.77070.22530.09940.058*
C200.9053 (3)0.1327 (2)0.4685 (2)0.0354 (7)
H20A0.91590.19240.50970.053*
H20B1.00970.13140.45040.053*
H20C0.86380.07080.49960.053*
N30.3688 (2)0.35893 (17)0.85114 (15)0.0238 (5)
H30.318 (3)0.344 (2)0.7975 (9)0.029*
O50.6154 (2)0.34703 (15)0.81535 (13)0.0318 (5)
O60.6912 (2)0.37267 (16)1.01601 (14)0.0358 (5)
C210.5233 (3)0.35717 (19)0.86965 (18)0.0243 (6)
C220.5623 (3)0.36974 (19)0.97550 (18)0.0248 (6)
C230.4129 (3)0.37657 (18)1.00930 (17)0.0225 (5)
C240.3723 (3)0.3857 (2)1.09591 (18)0.0270 (6)
H240.44970.39051.14750.032*
C250.2169 (3)0.3880 (2)1.10712 (19)0.0286 (6)
C260.1068 (3)0.3803 (2)1.02911 (19)0.0278 (6)
H260.00090.38251.03710.033*
C270.1434 (3)0.36965 (19)0.94057 (18)0.0245 (6)
C280.3001 (3)0.36819 (18)0.93224 (17)0.0216 (5)
C290.1678 (4)0.3968 (3)1.2013 (2)0.0401 (7)
H29A0.18480.33881.23560.060*
H29B0.05490.39741.19620.060*
H29C0.23180.46001.23310.060*
C300.0199 (3)0.3593 (2)0.8587 (2)0.0361 (7)
H30A0.04860.41790.82130.054*
H30B0.08430.35650.87910.054*
H30C0.01510.29670.82260.054*
N40.5103 (2)0.35401 (17)0.62544 (15)0.0252 (5)
H4A0.554 (3)0.350 (2)0.6800 (8)0.030*
O70.2527 (2)0.34008 (15)0.65678 (13)0.0339 (5)
O80.2033 (2)0.37014 (16)0.45880 (14)0.0369 (5)
C310.3544 (3)0.35165 (19)0.60458 (18)0.0256 (6)
C320.3291 (3)0.36678 (19)0.50041 (18)0.0255 (6)
C330.4871 (3)0.37722 (18)0.47077 (17)0.0221 (5)
C340.5404 (3)0.39321 (19)0.38603 (18)0.0255 (6)
H340.46870.39900.33420.031*
C350.7010 (3)0.40072 (19)0.37810 (18)0.0260 (6)
C360.8016 (3)0.39118 (19)0.45634 (19)0.0280 (6)
H360.91040.39550.45060.034*
C370.7510 (3)0.37566 (19)0.54253 (18)0.0240 (6)
C380.5905 (3)0.36892 (18)0.54667 (17)0.0219 (5)
C390.7648 (4)0.4188 (2)0.2880 (2)0.0372 (7)
H39A0.70930.36310.24380.056*
H39B0.87890.42170.29560.056*
H39C0.74760.48320.26590.056*
C400.8614 (3)0.3659 (2)0.6257 (2)0.0349 (7)
H40A0.86440.42020.67140.052*
H40B0.96860.37130.60880.052*
H40C0.82320.29970.65110.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0199 (11)0.0291 (12)0.0230 (12)0.0071 (9)0.0016 (9)0.0024 (9)
O10.0239 (10)0.0527 (13)0.0358 (12)0.0127 (9)0.0098 (9)0.0065 (9)
O20.0222 (11)0.0554 (13)0.0399 (12)0.0146 (9)0.0006 (9)0.0065 (10)
C10.0161 (13)0.0262 (13)0.0350 (15)0.0072 (10)0.0069 (11)0.0036 (11)
C20.0190 (13)0.0238 (13)0.0333 (15)0.0062 (10)0.0025 (11)0.0033 (11)
C30.0191 (13)0.0195 (12)0.0311 (15)0.0053 (9)0.0019 (10)0.0020 (10)
C40.0229 (14)0.0271 (14)0.0283 (15)0.0065 (10)0.0026 (11)0.0047 (11)
C50.0260 (14)0.0231 (13)0.0329 (15)0.0052 (10)0.0092 (11)0.0031 (11)
C60.0197 (13)0.0251 (13)0.0384 (16)0.0058 (10)0.0101 (11)0.0043 (11)
C70.0172 (12)0.0196 (12)0.0341 (15)0.0036 (9)0.0042 (10)0.0020 (10)
C80.0185 (12)0.0182 (12)0.0245 (13)0.0038 (9)0.0046 (10)0.0027 (10)
C90.0326 (16)0.0420 (17)0.0375 (17)0.0072 (13)0.0150 (13)0.0051 (13)
C100.0191 (14)0.0399 (16)0.0407 (17)0.0080 (11)0.0005 (12)0.0041 (13)
N20.0188 (11)0.0338 (12)0.0268 (12)0.0075 (9)0.0019 (9)0.0012 (10)
O30.0230 (10)0.0578 (14)0.0319 (11)0.0126 (9)0.0094 (9)0.0029 (10)
O40.0188 (10)0.0629 (15)0.0436 (13)0.0160 (9)0.0017 (9)0.0034 (11)
C110.0201 (13)0.0289 (14)0.0321 (15)0.0060 (10)0.0033 (11)0.0015 (11)
C120.0193 (14)0.0300 (14)0.0333 (15)0.0072 (10)0.0028 (11)0.0001 (11)
C130.0187 (13)0.0225 (13)0.0311 (15)0.0057 (10)0.0007 (11)0.0017 (11)
C140.0236 (14)0.0279 (14)0.0305 (15)0.0067 (10)0.0027 (11)0.0013 (11)
C150.0274 (14)0.0204 (13)0.0372 (16)0.0051 (10)0.0088 (12)0.0002 (11)
C160.0187 (13)0.0245 (13)0.0407 (16)0.0061 (10)0.0085 (11)0.0013 (11)
C170.0184 (13)0.0204 (13)0.0376 (16)0.0051 (10)0.0031 (11)0.0015 (11)
C180.0185 (13)0.0200 (12)0.0336 (15)0.0059 (9)0.0030 (11)0.0002 (10)
C190.0359 (17)0.0427 (17)0.0395 (18)0.0075 (13)0.0145 (14)0.0045 (14)
C200.0220 (14)0.0430 (17)0.0413 (18)0.0106 (12)0.0015 (12)0.0007 (13)
N30.0190 (11)0.0321 (12)0.0207 (11)0.0063 (9)0.0044 (9)0.0020 (9)
O50.0221 (10)0.0433 (12)0.0323 (11)0.0099 (8)0.0086 (8)0.0037 (9)
O60.0199 (10)0.0514 (13)0.0364 (12)0.0112 (9)0.0012 (8)0.0056 (9)
C210.0212 (13)0.0256 (13)0.0267 (14)0.0056 (10)0.0042 (11)0.0042 (10)
C220.0209 (14)0.0249 (13)0.0287 (14)0.0057 (10)0.0028 (11)0.0056 (11)
C230.0178 (12)0.0231 (13)0.0256 (14)0.0039 (10)0.0013 (10)0.0002 (10)
C240.0235 (14)0.0312 (14)0.0258 (14)0.0057 (11)0.0031 (11)0.0007 (11)
C250.0264 (14)0.0322 (15)0.0293 (15)0.0085 (11)0.0088 (11)0.0016 (11)
C260.0211 (13)0.0303 (14)0.0337 (15)0.0074 (10)0.0078 (11)0.0042 (11)
C270.0166 (13)0.0274 (14)0.0306 (15)0.0067 (10)0.0032 (10)0.0042 (11)
C280.0196 (12)0.0213 (12)0.0246 (13)0.0051 (9)0.0046 (10)0.0024 (10)
C290.0326 (16)0.058 (2)0.0316 (17)0.0118 (14)0.0108 (13)0.0025 (14)
C300.0191 (14)0.0547 (19)0.0364 (17)0.0132 (12)0.0008 (12)0.0108 (14)
N40.0198 (11)0.0353 (12)0.0233 (12)0.0101 (9)0.0056 (9)0.0059 (10)
O70.0240 (10)0.0474 (12)0.0331 (11)0.0106 (8)0.0112 (8)0.0061 (9)
O80.0200 (10)0.0542 (13)0.0386 (12)0.0135 (9)0.0015 (9)0.0056 (10)
C310.0205 (13)0.0285 (14)0.0300 (15)0.0090 (10)0.0055 (11)0.0050 (11)
C320.0191 (13)0.0273 (14)0.0306 (15)0.0063 (10)0.0035 (11)0.0035 (11)
C330.0178 (13)0.0239 (13)0.0257 (14)0.0068 (10)0.0033 (10)0.0016 (10)
C340.0244 (14)0.0293 (14)0.0221 (13)0.0061 (10)0.0009 (10)0.0013 (10)
C350.0238 (14)0.0250 (13)0.0299 (15)0.0047 (10)0.0088 (11)0.0007 (11)
C360.0195 (13)0.0260 (14)0.0387 (16)0.0050 (10)0.0062 (11)0.0021 (11)
C370.0171 (12)0.0234 (13)0.0319 (15)0.0065 (10)0.0015 (10)0.0010 (11)
C380.0199 (13)0.0204 (12)0.0263 (14)0.0056 (9)0.0045 (10)0.0016 (10)
C390.0380 (17)0.0395 (17)0.0359 (17)0.0082 (13)0.0155 (13)0.0006 (13)
C400.0199 (14)0.0480 (18)0.0370 (17)0.0113 (12)0.0006 (12)0.0044 (13)
Geometric parameters (Å, º) top
N1—H10.860 (5)N3—H30.860 (5)
N1—C11.348 (3)N3—C211.350 (3)
N1—C81.418 (3)N3—C281.413 (3)
O1—C11.219 (3)O5—C211.223 (3)
O2—C21.209 (3)O6—C221.204 (3)
C1—C21.562 (4)C21—C221.560 (4)
C2—C31.469 (3)C22—C231.467 (3)
C3—C41.387 (4)C23—C241.375 (4)
C3—C81.399 (4)C23—C281.403 (3)
C4—H40.9500C24—H240.9500
C4—C51.390 (4)C24—C251.390 (4)
C5—C61.398 (4)C25—C261.401 (4)
C5—C91.510 (4)C25—C291.511 (4)
C6—H60.9500C26—H260.9500
C6—C71.404 (4)C26—C271.393 (4)
C7—C81.380 (3)C27—C281.389 (3)
C7—C101.496 (4)C27—C301.508 (4)
C9—H9A0.9800C29—H29A0.9800
C9—H9B0.9800C29—H29B0.9800
C9—H9C0.9800C29—H29C0.9800
C10—H10A0.9800C30—H30A0.9800
C10—H10B0.9800C30—H30B0.9800
C10—H10C0.9800C30—H30C0.9800
N2—H20.860 (5)N4—H4A0.862 (5)
N2—C111.338 (3)N4—C311.352 (3)
N2—C181.414 (3)N4—C381.418 (3)
O3—C111.231 (3)O7—C311.223 (3)
O4—C121.208 (3)O8—C321.207 (3)
C11—C121.561 (4)C31—C321.558 (4)
C12—C131.465 (4)C32—C331.467 (3)
C13—C141.382 (4)C33—C341.388 (4)
C13—C181.394 (4)C33—C381.384 (4)
C14—H140.9500C34—H340.9500
C14—C151.395 (4)C34—C351.398 (4)
C15—C161.401 (4)C35—C361.401 (4)
C15—C191.507 (4)C35—C391.503 (4)
C16—H160.9500C36—H360.9500
C16—C171.393 (4)C36—C371.399 (4)
C17—C181.386 (3)C37—C381.388 (3)
C17—C201.502 (4)C37—C401.505 (4)
C19—H19A0.9800C39—H39A0.9800
C19—H19B0.9800C39—H39B0.9800
C19—H19C0.9800C39—H39C0.9800
C20—H20A0.9800C40—H40A0.9800
C20—H20B0.9800C40—H40B0.9800
C20—H20C0.9800C40—H40C0.9800
C1—N1—H1125 (2)C21—N3—H3122.3 (19)
C1—N1—C8111.6 (2)C21—N3—C28111.0 (2)
C8—N1—H1124 (2)C28—N3—H3126 (2)
N1—C1—C2106.0 (2)N3—C21—C22106.2 (2)
O1—C1—N1128.3 (3)O5—C21—N3127.6 (2)
O1—C1—C2125.7 (2)O5—C21—C22126.2 (2)
O2—C2—C1124.1 (2)O6—C22—C21124.2 (2)
O2—C2—C3131.1 (3)O6—C22—C23130.6 (3)
C3—C2—C1104.8 (2)C23—C22—C21105.2 (2)
C4—C3—C2131.6 (2)C24—C23—C22132.2 (2)
C4—C3—C8121.2 (2)C24—C23—C28121.3 (2)
C8—C3—C2107.2 (2)C28—C23—C22106.4 (2)
C3—C4—H4120.8C23—C24—H24120.4
C3—C4—C5118.5 (2)C23—C24—C25119.2 (2)
C5—C4—H4120.8C25—C24—H24120.4
C4—C5—C6118.7 (2)C24—C25—C26118.4 (2)
C4—C5—C9121.0 (3)C24—C25—C29120.6 (3)
C6—C5—C9120.3 (2)C26—C25—C29121.0 (2)
C5—C6—H6117.9C25—C26—H26118.1
C5—C6—C7124.2 (2)C27—C26—C25123.8 (2)
C7—C6—H6117.9C27—C26—H26118.1
C6—C7—C10122.6 (2)C26—C27—C30122.0 (2)
C8—C7—C6115.0 (2)C28—C27—C26116.0 (2)
C8—C7—C10122.4 (2)C28—C27—C30122.0 (2)
C3—C8—N1110.3 (2)C23—C28—N3111.1 (2)
C7—C8—N1127.3 (2)C27—C28—N3127.7 (2)
C7—C8—C3122.3 (2)C27—C28—C23121.2 (2)
C5—C9—H9A109.5C25—C29—H29A109.5
C5—C9—H9B109.5C25—C29—H29B109.5
C5—C9—H9C109.5C25—C29—H29C109.5
H9A—C9—H9B109.5H29A—C29—H29B109.5
H9A—C9—H9C109.5H29A—C29—H29C109.5
H9B—C9—H9C109.5H29B—C29—H29C109.5
C7—C10—H10A109.5C27—C30—H30A109.5
C7—C10—H10B109.5C27—C30—H30B109.5
C7—C10—H10C109.5C27—C30—H30C109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
C11—N2—H2122 (2)C31—N4—H4A123 (2)
C11—N2—C18111.5 (2)C31—N4—C38110.7 (2)
C18—N2—H2126 (2)C38—N4—H4A126 (2)
N2—C11—C12106.3 (2)N4—C31—C32106.4 (2)
O3—C11—N2127.5 (3)O7—C31—N4127.1 (3)
O3—C11—C12126.2 (2)O7—C31—C32126.5 (2)
O4—C12—C11124.1 (2)O8—C32—C31124.3 (2)
O4—C12—C13131.4 (3)O8—C32—C33131.2 (3)
C13—C12—C11104.5 (2)C33—C32—C31104.5 (2)
C14—C13—C12131.6 (2)C34—C33—C32131.6 (2)
C14—C13—C18121.1 (2)C38—C33—C32107.4 (2)
C18—C13—C12107.2 (2)C38—C33—C34121.0 (2)
C13—C14—H14120.5C33—C34—H34120.5
C13—C14—C15119.0 (3)C33—C34—C35119.0 (2)
C15—C14—H14120.5C35—C34—H34120.5
C14—C15—C16118.2 (3)C34—C35—C36118.3 (2)
C14—C15—C19121.1 (3)C34—C35—C39121.0 (3)
C16—C15—C19120.7 (2)C36—C35—C39120.7 (2)
C15—C16—H16117.9C35—C36—H36118.1
C17—C16—C15124.1 (2)C37—C36—C35123.8 (2)
C17—C16—H16117.9C37—C36—H36118.1
C16—C17—C20122.7 (2)C36—C37—C40122.8 (2)
C18—C17—C16115.6 (2)C38—C37—C36115.6 (2)
C18—C17—C20121.7 (3)C38—C37—C40121.6 (2)
C13—C18—N2110.5 (2)C33—C38—N4111.0 (2)
C17—C18—N2127.6 (2)C33—C38—C37122.4 (2)
C17—C18—C13121.9 (2)C37—C38—N4126.6 (2)
C15—C19—H19A109.5C35—C39—H39A109.5
C15—C19—H19B109.5C35—C39—H39B109.5
C15—C19—H19C109.5C35—C39—H39C109.5
H19A—C19—H19B109.5H39A—C39—H39B109.5
H19A—C19—H19C109.5H39A—C39—H39C109.5
H19B—C19—H19C109.5H39B—C39—H39C109.5
C17—C20—H20A109.5C37—C40—H40A109.5
C17—C20—H20B109.5C37—C40—H40B109.5
C17—C20—H20C109.5C37—C40—H40C109.5
H20A—C20—H20B109.5H40A—C40—H40B109.5
H20A—C20—H20C109.5H40A—C40—H40C109.5
H20B—C20—H20C109.5H40B—C40—H40C109.5
N1—C1—C2—O2179.8 (2)N3—C21—C22—O6179.1 (2)
N1—C1—C2—C30.0 (3)N3—C21—C22—C230.8 (3)
O1—C1—C2—O20.2 (4)O5—C21—C22—O61.4 (4)
O1—C1—C2—C3179.5 (3)O5—C21—C22—C23178.7 (2)
O2—C2—C3—C40.6 (5)O6—C22—C23—C241.8 (5)
O2—C2—C3—C8179.3 (3)O6—C22—C23—C28179.7 (3)
C1—N1—C8—C30.8 (3)C21—N3—C28—C232.1 (3)
C1—N1—C8—C7178.4 (2)C21—N3—C28—C27178.0 (2)
C1—C2—C3—C4179.6 (3)C21—C22—C23—C24178.2 (3)
C1—C2—C3—C80.5 (3)C21—C22—C23—C280.4 (3)
C2—C3—C4—C5179.5 (2)C22—C23—C24—C25178.4 (3)
C2—C3—C8—N10.8 (3)C22—C23—C28—N31.4 (3)
C2—C3—C8—C7178.5 (2)C22—C23—C28—C27178.7 (2)
C3—C4—C5—C60.3 (4)C23—C24—C25—C260.2 (4)
C3—C4—C5—C9179.4 (2)C23—C24—C25—C29179.4 (3)
C4—C3—C8—N1179.3 (2)C24—C23—C28—N3179.6 (2)
C4—C3—C8—C71.4 (4)C24—C23—C28—C270.5 (4)
C4—C5—C6—C70.1 (4)C24—C25—C26—C270.6 (4)
C5—C6—C7—C80.8 (4)C25—C26—C27—C280.9 (4)
C5—C6—C7—C10178.8 (2)C25—C26—C27—C30178.6 (3)
C6—C7—C8—N1179.3 (2)C26—C27—C28—N3179.6 (2)
C6—C7—C8—C31.6 (3)C26—C27—C28—C230.3 (4)
C8—N1—C1—O1179.0 (3)C28—N3—C21—O5177.8 (3)
C8—N1—C1—C20.5 (3)C28—N3—C21—C221.7 (3)
C8—C3—C4—C50.4 (4)C28—C23—C24—C250.8 (4)
C9—C5—C6—C7179.6 (2)C29—C25—C26—C27178.5 (3)
C10—C7—C8—N11.1 (4)C30—C27—C28—N31.0 (4)
C10—C7—C8—C3178.1 (2)C30—C27—C28—C23179.1 (2)
N2—C11—C12—O4179.2 (3)N4—C31—C32—O8178.9 (3)
N2—C11—C12—C130.4 (3)N4—C31—C32—C330.1 (3)
O3—C11—C12—O40.2 (4)O7—C31—C32—O81.0 (4)
O3—C11—C12—C13179.0 (3)O7—C31—C32—C33179.8 (3)
O4—C12—C13—C140.5 (5)O8—C32—C33—C340.7 (5)
O4—C12—C13—C18177.8 (3)O8—C32—C33—C38178.9 (3)
C11—N2—C18—C132.1 (3)C31—N4—C38—C330.2 (3)
C11—N2—C18—C17176.9 (2)C31—N4—C38—C37179.7 (2)
C11—C12—C13—C14178.2 (3)C31—C32—C33—C34179.3 (3)
C11—C12—C13—C180.8 (3)C31—C32—C33—C380.2 (3)
C12—C13—C14—C15177.4 (3)C32—C33—C34—C35179.6 (2)
C12—C13—C18—N21.8 (3)C32—C33—C38—N40.3 (3)
C12—C13—C18—C17177.3 (2)C32—C33—C38—C37179.8 (2)
C13—C14—C15—C160.9 (4)C33—C34—C35—C360.3 (4)
C13—C14—C15—C19179.9 (2)C33—C34—C35—C39179.6 (2)
C14—C13—C18—N2179.5 (2)C34—C33—C38—N4179.3 (2)
C14—C13—C18—C170.4 (4)C34—C33—C38—C370.2 (4)
C14—C15—C16—C170.8 (4)C34—C35—C36—C370.8 (4)
C15—C16—C17—C180.1 (4)C35—C36—C37—C380.7 (4)
C15—C16—C17—C20179.3 (2)C35—C36—C37—C40179.9 (2)
C16—C17—C18—N2179.4 (2)C36—C37—C38—N4179.6 (2)
C16—C17—C18—C130.5 (4)C36—C37—C38—C330.2 (4)
C18—N2—C11—O3177.9 (3)C38—N4—C31—O7180.0 (3)
C18—N2—C11—C121.5 (3)C38—N4—C31—C320.0 (3)
C18—C13—C14—C150.3 (4)C38—C33—C34—C350.1 (4)
C19—C15—C16—C17179.8 (2)C39—C35—C36—C37179.1 (2)
C20—C17—C18—N20.2 (4)C40—C37—C38—N40.9 (4)
C20—C17—C18—C13178.7 (2)C40—C37—C38—C33179.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (1)2.07 (1)2.903 (3)164 (3)
N2—H2···O10.86 (1)2.04 (1)2.890 (3)169 (3)
N3—H3···O70.86 (1)2.09 (1)2.922 (3)163 (3)
N4—H4A···O50.86 (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

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