organic compounds
5,7-Dimethyl-1H-indole-2,3-dione
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
The title compound, C10H9NO2, crystallizes with four molecules in the 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 H-indole-2,3-dione: there are four of these 5,7-dimethylisatin molecules in the (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).
of 5,7-dimethyl-1In 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.
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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 .
details are summarized in Table 2Structural data
CCDC reference: 1539183
https://doi.org/10.1107/S2414314617004448/hb4133sup1.cif
contains datablock I. DOI: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
Data collection: APEX2 (Bruker, 2014); cell
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).C10H9NO2 | Z = 8 |
Mr = 175.18 | F(000) = 736 |
Triclinic, P1 | Dx = 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 |
Bruker D8 Venture diffractometer | 4523 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.060 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 25.4°, θmin = 2.8° |
Tmin = 0.692, Tmax = 0.745 | h = −10→10 |
56302 measured reflections | k = −16→16 |
6187 independent reflections | l = −17→17 |
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(Fo2) + (0.0802P)2 + 1.7614P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
6187 reflections | Δρmax = 0.39 e Å−3 |
489 parameters | Δρmin = −0.27 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 Scienceshttps://doi.org/10.13039/100000086 (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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