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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161757
https://doi.org/10.1107/S2414314616017570

9H-Carbazole-9-carbaldehyde

CROSSMARK_Color_square_no_text.svg
Cong Wang,a,b An-Ran Wanga,b and Sheng-Li Lia,b*

aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
*Correspondence e-mail: lsl1968@ahu.edu.cn

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 September 2016; accepted 2 November 2016; online 15 November 2016)

The title carbazole derivative, C13H9NO, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the planar carbazole ring system and the aldehyde group (HC=O) is 3.3 (2)° in A and 7.5 (2)° in B, indicating that the mol­ecules are both nearly planar. In the crystal, the A and B mol­ecules are linked by a C—H⋯O hydrogen bond and stack along the b-axis direction. The structure was refined as a two component twin with a refined BASF value of 0.102 (2).

CCDC reference: 1439578

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

Structure description

Carbazole derivatives are important compounds because of their wide range of biological activities, and also owing to their high electron affinity, hole transport properties and good planarity, which make them appropriate building blocks in the construction of chromophores for non-linear optical materials (Li et al. 2013[Li, S. L., Gao, C., Liu, F. & Wei, W. (2013). React. Funct. Polym. 73, 828-832.]; Jiang et al. 2016[Jiang, D., Chen, S. C., Xue, Z., Li, Y. L., Liu, H. B., Yang, W. S. & Li, Y. L. (2016). Dyes Pigments, 125, 100-105.]). Since carbazole derivatives have relatively low toxicity, they have been widely used in the biological area (Fei et al. 2015[Fei, X. N., Li, R., Lin, D. Y., Gu, Y. C. & Yu, L. (2015). J. Fluoresc. 25, 1251-1258.]; Wang et al. 2016[Wang, G., Chen, H., Chen, X. & Xie, Y. (2016). RSC Adv. 6, 18662-18666.]).

The title compound, Fig. 1[link], crystallized with two independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule A, the aldehyde group (H13—C13=O1) is inclined to the planar carbazole ring system [N1/C1–C12; planar to within 0.019 (2) Å] by 3.3 (2)°. In mol­ecule B, the aldehyde group (H27—C27=O2) is inclined to the planar carbazole ring system [N2/C15–C26; planar to within 0.014 (2) Å] by 7.5 (2)°. Hence, the two mol­ecules are both almost planar. The geometrical parameters of the title compound are similar to those observed for 9-benzoyl­carbazole (Claramunt et al., 2002[Claramunt, R. M., Cornago, P., Sanz, D., Santa-Mar\?ía, M. D., Foces-Foces, C., Alkorta, I. & Elguero, J. (2002). J. Mol. Struct. 605, 199-212.]).

[Figure 1]
Figure 1
The mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, the A and B mol­ecules are linked by a C—H⋯O hydrogen bond and stack along the b-axis direction (Table 1[link] and Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C27—H27⋯O1i 0.93 2.47 3.378 (3) 166
Symmetry code: (i) [-x, y-{\script{3\over 2}}, -z+1].
[Figure 2]
Figure 2
A view along the b axis of the crystal packing of the title compound. The A (blue) and B (red) mol­ecules are linked by a C—H⋯O hydrogen bond and stack along the b-axis direction (see Table 1[link]).

Synthesis and crystallization

The title compound was synthesized following a published procedure (Bose et al., 2006[Bose, A. K., Ganguly, S. N., Manhas, M. S., Guha, A. & Pombo-Villars, E. (2006). Tetrahedron Lett. 47, 4605-4607.]). A mixture of 1.67 g (10.0 mmol) of carbazole and 1.0–1.2 equiv. of aqueous 80% formic acid in toluene was reacted for 10 min under microwave irradiation (320 W). The reaction was monitored by TLC, and after starting material had disappeared, the mixture was evaporated to give the crude title compound. Further purification by flash chromatography on silica gel, using petroleum ether/ethyl acetate (1:10 v/v) as eluent, gave a pale-yellow solid (yield 75%). The solid was then dissolved in 10 ml absolute ethanol, filtered, and the filtrate evaporated slowly for a week, yielding yellow rod-like crystals of the title compound. 1H NMR (300 MHz, DMSO) δ 11.24 (s, 1H), 8.11 (d, J = 7.8 Hz, 2H), 7.48 (d, J = 8.1 Hz, 2H), 7.38 (t, J = 7.6 Hz, 2H), 7.15 (t, J = 7.4 Hz, 2H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The structure was refined as a two-component twin with a refined BASF value of 0.102 (2).

Table 2
Experimental details

Crystal data
Chemical formula C13H9NO
Mr 195.21
Crystal system, space group Monoclinic, P21
Temperature (K) 296
a, b, c (Å) 12.957 (2), 5.3621 (10), 14.440 (3)
β (°) 109.548 (2)
V (Å3) 945.4 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.30 × 0.20 × 0.20
 
Data collection
Diffractometer Bruker SMART CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections 3577, 3577, 3457
Rint 0.018
(sin θ/λ)max (Å−1) 0.644
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.076, 1.07
No. of reflections 3577
No. of parameters 273
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.20, −0.16
Computer programs: SMART and SAINT (Bruker, 2007[Bruker (2007). SMART, 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.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.])'.

Structural data

CCDC reference: 1439578

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314616017570/su4078sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017570/su4078Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616017570/su4078Isup3.cml

checkCIF report


Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010)'.

9H-Carbazole-9-carbaldehyde top
Crystal data top
C13H9NOF(000) = 408
Mr = 195.21Dx = 1.371 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 12.957 (2) ÅCell parameters from 5371 reflections
b = 5.3621 (10) Åθ = 2.6–27.0°
c = 14.440 (3) ŵ = 0.09 mm−1
β = 109.548 (2)°T = 296 K
V = 945.4 (3) Å3Rod, yellow
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area detector
diffractometer		3577 independent reflections
Radiation source: fine-focus sealed tube3457 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
phi and ω scansθmax = 27.2°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −16→16
Tmin = 0.974, Tmax = 0.983k = −6→6
3577 measured reflectionsl = −15→18
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0405P)2 + 0.1094P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.20 e Å−3
3577 reflectionsΔρmin = −0.16 e Å−3
273 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.011 (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.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.07452 (11)1.2319 (3)0.34069 (11)0.0349 (4)
N10.04534 (12)1.0956 (3)0.26573 (11)0.0241 (3)
C10.08756 (14)1.1098 (4)0.18707 (13)0.0238 (4)
C20.06519 (16)1.2822 (4)0.11060 (14)0.0290 (4)
H20.01551.41130.10480.035*
C30.11964 (17)1.2538 (4)0.04364 (14)0.0321 (5)
H30.10601.3655−0.00840.038*
C40.19488 (16)1.0603 (5)0.05256 (14)0.0319 (5)
H40.23051.04580.00660.038*
C50.21699 (15)0.8901 (4)0.12896 (14)0.0283 (4)
H50.26700.76170.13460.034*
C60.16291 (15)0.9149 (4)0.19725 (14)0.0236 (4)
C70.16787 (14)0.7763 (4)0.28531 (13)0.0223 (4)
C80.22834 (15)0.5698 (4)0.33153 (14)0.0274 (4)
H80.27610.49130.30510.033*
C90.21617 (16)0.4829 (4)0.41779 (15)0.0308 (5)
H90.25610.34500.44940.037*
C100.14431 (16)0.6008 (5)0.45775 (14)0.0313 (5)
H100.13770.54000.51580.038*
C110.08271 (15)0.8061 (4)0.41284 (14)0.0281 (4)
H110.03490.88360.43960.034*
C120.09520 (15)0.8919 (4)0.32609 (14)0.0236 (4)
C13−0.03400 (16)1.2500 (4)0.27651 (15)0.0296 (4)
H13−0.05871.37850.23120.036*
O20.16975 (11)0.3158 (3)0.83309 (10)0.0329 (4)
N20.29786 (12)0.3523 (3)0.75651 (11)0.0226 (4)
C150.34916 (14)0.2512 (4)0.69175 (12)0.0212 (4)
C160.31665 (15)0.0519 (4)0.62757 (13)0.0241 (4)
H160.2526−0.03580.62060.029*
C170.38418 (16)−0.0113 (4)0.57397 (14)0.0262 (4)
H170.3648−0.14400.53010.031*
C180.48043 (15)0.1204 (4)0.58462 (14)0.0268 (4)
H180.52440.07320.54820.032*
C190.51149 (15)0.3209 (4)0.64885 (14)0.0257 (4)
H190.57530.40920.65530.031*
C200.44523 (14)0.3873 (4)0.70346 (13)0.0216 (4)
C210.45419 (14)0.5768 (4)0.77753 (13)0.0225 (4)
C220.53065 (15)0.7648 (4)0.81761 (13)0.0258 (4)
H220.59160.78350.79790.031*
C230.51438 (17)0.9228 (4)0.88710 (14)0.0300 (4)
H230.56481.04880.91420.036*
C240.42294 (17)0.8954 (4)0.91706 (14)0.0295 (4)
H240.41381.00390.96400.035*
C250.34560 (16)0.7107 (4)0.87868 (14)0.0266 (4)
H250.28480.69340.89870.032*
C260.36272 (15)0.5518 (4)0.80878 (13)0.0218 (4)
C270.20807 (15)0.2484 (4)0.77125 (14)0.0264 (4)
H270.17390.11640.73080.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0335 (7)0.0374 (9)0.0392 (8)0.0030 (7)0.0195 (6)−0.0046 (7)
N10.0228 (7)0.0241 (9)0.0265 (8)−0.0001 (7)0.0097 (6)−0.0009 (7)
C10.0213 (8)0.0260 (10)0.0237 (9)−0.0040 (8)0.0072 (7)−0.0048 (8)
C20.0304 (10)0.0264 (11)0.0283 (10)−0.0004 (9)0.0071 (8)−0.0005 (9)
C30.0385 (11)0.0324 (12)0.0229 (10)−0.0069 (10)0.0071 (8)0.0030 (9)
C40.0333 (10)0.0398 (13)0.0252 (10)−0.0057 (10)0.0131 (8)−0.0043 (9)
C50.0267 (10)0.0316 (11)0.0284 (10)0.0009 (9)0.0116 (8)−0.0032 (9)
C60.0213 (9)0.0227 (10)0.0251 (9)−0.0025 (7)0.0055 (7)−0.0028 (8)
C70.0205 (8)0.0234 (10)0.0233 (9)−0.0034 (8)0.0078 (7)−0.0038 (8)
C80.0242 (9)0.0257 (11)0.0310 (10)0.0008 (8)0.0073 (8)−0.0004 (9)
C90.0287 (10)0.0276 (11)0.0316 (10)−0.0002 (8)0.0041 (8)0.0053 (9)
C100.0315 (10)0.0371 (12)0.0243 (9)−0.0084 (10)0.0079 (8)0.0032 (9)
C110.0268 (9)0.0333 (11)0.0259 (9)−0.0052 (9)0.0109 (8)−0.0031 (8)
C120.0210 (8)0.0238 (10)0.0249 (9)−0.0042 (8)0.0062 (7)−0.0029 (8)
C130.0271 (9)0.0267 (11)0.0347 (11)0.0029 (8)0.0100 (8)−0.0027 (9)
O20.0333 (7)0.0396 (10)0.0322 (7)0.0029 (7)0.0194 (6)0.0050 (7)
N20.0239 (8)0.0236 (9)0.0222 (8)0.0019 (6)0.0103 (6)0.0011 (6)
C150.0233 (8)0.0219 (10)0.0195 (8)0.0043 (8)0.0087 (7)0.0049 (8)
C160.0249 (9)0.0228 (10)0.0240 (9)−0.0013 (8)0.0073 (7)0.0026 (8)
C170.0340 (10)0.0233 (10)0.0204 (9)0.0020 (8)0.0080 (8)−0.0015 (8)
C180.0298 (9)0.0305 (11)0.0238 (9)0.0036 (8)0.0139 (8)0.0014 (8)
C190.0240 (9)0.0298 (11)0.0256 (9)−0.0001 (8)0.0112 (8)0.0030 (8)
C200.0249 (9)0.0190 (9)0.0206 (9)0.0010 (7)0.0071 (7)0.0039 (8)
C210.0254 (9)0.0216 (10)0.0201 (8)0.0031 (8)0.0071 (7)0.0045 (8)
C220.0278 (9)0.0257 (11)0.0233 (9)−0.0016 (8)0.0076 (7)0.0035 (8)
C230.0353 (11)0.0253 (11)0.0260 (10)−0.0018 (9)0.0059 (8)0.0009 (8)
C240.0398 (11)0.0260 (11)0.0209 (9)0.0051 (9)0.0079 (8)−0.0012 (8)
C250.0299 (9)0.0273 (11)0.0239 (9)0.0063 (8)0.0109 (8)0.0032 (8)
C260.0246 (9)0.0207 (10)0.0194 (8)0.0031 (7)0.0063 (7)0.0043 (7)
C270.0246 (9)0.0282 (11)0.0278 (9)0.0007 (8)0.0106 (8)0.0070 (8)
Geometric parameters (Å, º) top
O1—C131.212 (2)O2—C271.213 (2)
N1—C131.369 (3)N2—C271.369 (2)
N1—C121.412 (3)N2—C261.413 (2)
N1—C11.418 (2)N2—C151.423 (2)
C1—C21.394 (3)C15—C161.385 (3)
C1—C61.404 (3)C15—C201.403 (3)
C2—C31.383 (3)C16—C171.390 (3)
C2—H20.9300C16—H160.9300
C3—C41.400 (3)C17—C181.396 (3)
C3—H30.9300C17—H170.9300
C4—C51.386 (3)C18—C191.389 (3)
C4—H40.9300C18—H180.9300
C5—C61.394 (3)C19—C201.392 (3)
C5—H50.9300C19—H190.9300
C6—C71.456 (3)C20—C211.452 (3)
C7—C81.391 (3)C21—C221.396 (3)
C7—C121.410 (2)C21—C261.409 (2)
C8—C91.387 (3)C22—C231.382 (3)
C8—H80.9300C22—H220.9300
C9—C101.400 (3)C23—C241.398 (3)
C9—H90.9300C23—H230.9300
C10—C111.387 (3)C24—C251.386 (3)
C10—H100.9300C24—H240.9300
C11—C121.394 (3)C25—C261.394 (3)
C11—H110.9300C25—H250.9300
C13—H130.9300C27—H270.9300
C13—N1—C12127.14 (16)C27—N2—C26127.54 (16)
C13—N1—C1124.34 (17)C27—N2—C15123.73 (18)
C12—N1—C1108.47 (15)C26—N2—C15108.31 (15)
C2—C1—C6121.97 (17)C16—C15—C20122.73 (16)
C2—C1—N1129.53 (18)C16—C15—N2128.99 (17)
C6—C1—N1108.48 (17)C20—C15—N2108.27 (16)
C3—C2—C1117.48 (19)C15—C16—C17116.96 (17)
C3—C2—H2121.3C15—C16—H16121.5
C1—C2—H2121.3C17—C16—H16121.5
C2—C3—C4121.31 (19)C16—C17—C18121.40 (18)
C2—C3—H3119.3C16—C17—H17119.3
C4—C3—H3119.3C18—C17—H17119.3
C5—C4—C3120.90 (18)C19—C18—C17120.91 (17)
C5—C4—H4119.6C19—C18—H18119.5
C3—C4—H4119.6C17—C18—H18119.5
C4—C5—C6118.78 (19)C18—C19—C20118.70 (18)
C4—C5—H5120.6C18—C19—H19120.6
C6—C5—H5120.6C20—C19—H19120.6
C5—C6—C1119.56 (18)C19—C20—C15119.29 (18)
C5—C6—C7133.13 (19)C19—C20—C21133.13 (18)
C1—C6—C7107.31 (16)C15—C20—C21107.56 (15)
C8—C7—C12119.81 (18)C22—C21—C26119.50 (17)
C8—C7—C6132.74 (17)C22—C21—C20132.98 (16)
C12—C7—C6107.44 (17)C26—C21—C20107.51 (16)
C9—C8—C7118.89 (18)C23—C22—C21118.95 (17)
C9—C8—H8120.6C23—C22—H22120.5
C7—C8—H8120.6C21—C22—H22120.5
C8—C9—C10120.6 (2)C22—C23—C24120.72 (19)
C8—C9—H9119.7C22—C23—H23119.6
C10—C9—H9119.7C24—C23—H23119.6
C11—C10—C9121.61 (19)C25—C24—C23121.72 (19)
C11—C10—H10119.2C25—C24—H24119.1
C9—C10—H10119.2C23—C24—H24119.1
C10—C11—C12117.41 (19)C24—C25—C26117.21 (18)
C10—C11—H11121.3C24—C25—H25121.4
C12—C11—H11121.3C26—C25—H25121.4
C11—C12—C7121.65 (19)C25—C26—C21121.91 (18)
C11—C12—N1130.04 (18)C25—C26—N2129.73 (17)
C7—C12—N1108.30 (16)C21—C26—N2108.35 (15)
O1—C13—N1124.9 (2)O2—C27—N2124.9 (2)
O1—C13—H13117.6O2—C27—H27117.6
N1—C13—H13117.6N2—C27—H27117.6
C13—N1—C1—C24.3 (3)C27—N2—C15—C165.7 (3)
C12—N1—C1—C2−178.30 (19)C26—N2—C15—C16178.78 (18)
C13—N1—C1—C6−176.87 (18)C27—N2—C15—C20−173.23 (16)
C12—N1—C1—C60.5 (2)C26—N2—C15—C20−0.1 (2)
C6—C1—C2—C30.5 (3)C20—C15—C16—C170.2 (3)
N1—C1—C2—C3179.17 (19)N2—C15—C16—C17−178.55 (18)
C1—C2—C3—C4−0.4 (3)C15—C16—C17—C180.1 (3)
C2—C3—C4—C50.2 (3)C16—C17—C18—C19−0.5 (3)
C3—C4—C5—C6−0.1 (3)C17—C18—C19—C200.6 (3)
C4—C5—C6—C10.2 (3)C18—C19—C20—C15−0.3 (3)
C4—C5—C6—C7−178.6 (2)C18—C19—C20—C21177.9 (2)
C2—C1—C6—C5−0.4 (3)C16—C15—C20—C19−0.1 (3)
N1—C1—C6—C5−179.32 (17)N2—C15—C20—C19178.90 (16)
C2—C1—C6—C7178.65 (17)C16—C15—C20—C21−178.76 (17)
N1—C1—C6—C7−0.3 (2)N2—C15—C20—C210.2 (2)
C5—C6—C7—C8−0.3 (4)C19—C20—C21—C222.6 (4)
C1—C6—C7—C8−179.1 (2)C15—C20—C21—C22−179.0 (2)
C5—C6—C7—C12178.8 (2)C19—C20—C21—C26−178.7 (2)
C1—C6—C7—C12−0.1 (2)C15—C20—C21—C26−0.2 (2)
C12—C7—C8—C9−0.5 (3)C26—C21—C22—C23−0.2 (3)
C6—C7—C8—C9178.5 (2)C20—C21—C22—C23178.5 (2)
C7—C8—C9—C100.0 (3)C21—C22—C23—C240.0 (3)
C8—C9—C10—C110.4 (3)C22—C23—C24—C25−0.1 (3)
C9—C10—C11—C12−0.2 (3)C23—C24—C25—C260.2 (3)
C10—C11—C12—C7−0.3 (3)C24—C25—C26—C21−0.3 (3)
C10—C11—C12—N1−179.03 (19)C24—C25—C26—N2−178.85 (18)
C8—C7—C12—C110.6 (3)C22—C21—C26—C250.3 (3)
C6—C7—C12—C11−178.60 (18)C20—C21—C26—C25−178.64 (17)
C8—C7—C12—N1179.61 (16)C22—C21—C26—N2179.13 (16)
C6—C7—C12—N10.4 (2)C20—C21—C26—N20.2 (2)
C13—N1—C12—C11−4.4 (3)C27—N2—C26—C25−8.6 (3)
C1—N1—C12—C11178.3 (2)C15—N2—C26—C25178.65 (18)
C13—N1—C12—C7176.75 (18)C27—N2—C26—C21172.73 (18)
C1—N1—C12—C7−0.6 (2)C15—N2—C26—C210.0 (2)
C12—N1—C13—O1−0.7 (3)C26—N2—C27—O20.3 (3)
C1—N1—C13—O1176.17 (19)C15—N2—C27—O2172.09 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27···O1i0.932.473.378 (3)166
Symmetry code: (i) −x, y−3/2, −z+1.
 

Acknowledgements

This work was supported by Anhui Provincial Natural Science Foundation (1308085MB24) and the Educational Commission of Anhui Province of China (KJ2012A025).

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161757
https://doi.org/10.1107/S2414314616017570
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