organic compounds
9H-Carbazole-9-carbaldehyde
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
The title carbazole derivative, C13H9NO, crystallizes with two independent molecules (A and B) in the 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).
Keywords: crystal structure; carbazole; C—H⋯O hydrogen bond.
CCDC reference: 1439578
Structure description
Carbazole derivatives are important compounds because of their wide range of biological activities, and also owing to their high et al. 2013; Jiang et al. 2016). Since carbazole derivatives have relatively low toxicity, they have been widely used in the biological area (Fei et al. 2015; Wang et al. 2016).
hole transport properties and good planarity, which make them appropriate building blocks in the construction of chromophores for non-linear optical materials (LiThe title compound, Fig. 1, crystallized with two independent molecules (A and B) in the 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).
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 and Fig. 2).
Synthesis and crystallization
The title compound was synthesized following a published procedure (Bose et al., 2006). 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 on silica gel, using petroleum ether/ethyl acetate (1:10 v/v) as 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 . The structure was refined as a two-component twin with a refined BASF value of 0.102 (2).
details are summarized in Table 2Structural data
CCDC reference: 1439578
https://doi.org/10.1107/S2414314616017570/su4078sup1.cif
contains datablocks I, Global. DOI: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
Data collection: SMART (Bruker, 2007); cell
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)'.C13H9NO | F(000) = 408 |
Mr = 195.21 | Dx = 1.371 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.957 (2) Å | Cell parameters from 5371 reflections |
b = 5.3621 (10) Å | θ = 2.6–27.0° |
c = 14.440 (3) Å | µ = 0.09 mm−1 |
β = 109.548 (2)° | T = 296 K |
V = 945.4 (3) Å3 | Rod, yellow |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Bruker SMART CCD area detector diffractometer | 3577 independent reflections |
Radiation source: fine-focus sealed tube | 3457 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
phi and ω scans | θmax = 27.2°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −16→16 |
Tmin = 0.974, Tmax = 0.983 | k = −6→6 |
3577 measured reflections | l = −15→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.07 | Δρmax = 0.20 e Å−3 |
3577 reflections | Δρmin = −0.16 e Å−3 |
273 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.011 (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. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.07452 (11) | 1.2319 (3) | 0.34069 (11) | 0.0349 (4) | |
N1 | 0.04534 (12) | 1.0956 (3) | 0.26573 (11) | 0.0241 (3) | |
C1 | 0.08756 (14) | 1.1098 (4) | 0.18707 (13) | 0.0238 (4) | |
C2 | 0.06519 (16) | 1.2822 (4) | 0.11060 (14) | 0.0290 (4) | |
H2 | 0.0155 | 1.4113 | 0.1048 | 0.035* | |
C3 | 0.11964 (17) | 1.2538 (4) | 0.04364 (14) | 0.0321 (5) | |
H3 | 0.1060 | 1.3655 | −0.0084 | 0.038* | |
C4 | 0.19488 (16) | 1.0603 (5) | 0.05256 (14) | 0.0319 (5) | |
H4 | 0.2305 | 1.0458 | 0.0066 | 0.038* | |
C5 | 0.21699 (15) | 0.8901 (4) | 0.12896 (14) | 0.0283 (4) | |
H5 | 0.2670 | 0.7617 | 0.1346 | 0.034* | |
C6 | 0.16291 (15) | 0.9149 (4) | 0.19725 (14) | 0.0236 (4) | |
C7 | 0.16787 (14) | 0.7763 (4) | 0.28531 (13) | 0.0223 (4) | |
C8 | 0.22834 (15) | 0.5698 (4) | 0.33153 (14) | 0.0274 (4) | |
H8 | 0.2761 | 0.4913 | 0.3051 | 0.033* | |
C9 | 0.21617 (16) | 0.4829 (4) | 0.41779 (15) | 0.0308 (5) | |
H9 | 0.2561 | 0.3450 | 0.4494 | 0.037* | |
C10 | 0.14431 (16) | 0.6008 (5) | 0.45775 (14) | 0.0313 (5) | |
H10 | 0.1377 | 0.5400 | 0.5158 | 0.038* | |
C11 | 0.08271 (15) | 0.8061 (4) | 0.41284 (14) | 0.0281 (4) | |
H11 | 0.0349 | 0.8836 | 0.4396 | 0.034* | |
C12 | 0.09520 (15) | 0.8919 (4) | 0.32609 (14) | 0.0236 (4) | |
C13 | −0.03400 (16) | 1.2500 (4) | 0.27651 (15) | 0.0296 (4) | |
H13 | −0.0587 | 1.3785 | 0.2312 | 0.036* | |
O2 | 0.16975 (11) | 0.3158 (3) | 0.83309 (10) | 0.0329 (4) | |
N2 | 0.29786 (12) | 0.3523 (3) | 0.75651 (11) | 0.0226 (4) | |
C15 | 0.34916 (14) | 0.2512 (4) | 0.69175 (12) | 0.0212 (4) | |
C16 | 0.31665 (15) | 0.0519 (4) | 0.62757 (13) | 0.0241 (4) | |
H16 | 0.2526 | −0.0358 | 0.6206 | 0.029* | |
C17 | 0.38418 (16) | −0.0113 (4) | 0.57397 (14) | 0.0262 (4) | |
H17 | 0.3648 | −0.1440 | 0.5301 | 0.031* | |
C18 | 0.48043 (15) | 0.1204 (4) | 0.58462 (14) | 0.0268 (4) | |
H18 | 0.5244 | 0.0732 | 0.5482 | 0.032* | |
C19 | 0.51149 (15) | 0.3209 (4) | 0.64885 (14) | 0.0257 (4) | |
H19 | 0.5753 | 0.4092 | 0.6553 | 0.031* | |
C20 | 0.44523 (14) | 0.3873 (4) | 0.70346 (13) | 0.0216 (4) | |
C21 | 0.45419 (14) | 0.5768 (4) | 0.77753 (13) | 0.0225 (4) | |
C22 | 0.53065 (15) | 0.7648 (4) | 0.81761 (13) | 0.0258 (4) | |
H22 | 0.5916 | 0.7835 | 0.7979 | 0.031* | |
C23 | 0.51438 (17) | 0.9228 (4) | 0.88710 (14) | 0.0300 (4) | |
H23 | 0.5648 | 1.0488 | 0.9142 | 0.036* | |
C24 | 0.42294 (17) | 0.8954 (4) | 0.91706 (14) | 0.0295 (4) | |
H24 | 0.4138 | 1.0039 | 0.9640 | 0.035* | |
C25 | 0.34560 (16) | 0.7107 (4) | 0.87868 (14) | 0.0266 (4) | |
H25 | 0.2848 | 0.6934 | 0.8987 | 0.032* | |
C26 | 0.36272 (15) | 0.5518 (4) | 0.80878 (13) | 0.0218 (4) | |
C27 | 0.20807 (15) | 0.2484 (4) | 0.77125 (14) | 0.0264 (4) | |
H27 | 0.1739 | 0.1164 | 0.7308 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0335 (7) | 0.0374 (9) | 0.0392 (8) | 0.0030 (7) | 0.0195 (6) | −0.0046 (7) |
N1 | 0.0228 (7) | 0.0241 (9) | 0.0265 (8) | −0.0001 (7) | 0.0097 (6) | −0.0009 (7) |
C1 | 0.0213 (8) | 0.0260 (10) | 0.0237 (9) | −0.0040 (8) | 0.0072 (7) | −0.0048 (8) |
C2 | 0.0304 (10) | 0.0264 (11) | 0.0283 (10) | −0.0004 (9) | 0.0071 (8) | −0.0005 (9) |
C3 | 0.0385 (11) | 0.0324 (12) | 0.0229 (10) | −0.0069 (10) | 0.0071 (8) | 0.0030 (9) |
C4 | 0.0333 (10) | 0.0398 (13) | 0.0252 (10) | −0.0057 (10) | 0.0131 (8) | −0.0043 (9) |
C5 | 0.0267 (10) | 0.0316 (11) | 0.0284 (10) | 0.0009 (9) | 0.0116 (8) | −0.0032 (9) |
C6 | 0.0213 (9) | 0.0227 (10) | 0.0251 (9) | −0.0025 (7) | 0.0055 (7) | −0.0028 (8) |
C7 | 0.0205 (8) | 0.0234 (10) | 0.0233 (9) | −0.0034 (8) | 0.0078 (7) | −0.0038 (8) |
C8 | 0.0242 (9) | 0.0257 (11) | 0.0310 (10) | 0.0008 (8) | 0.0073 (8) | −0.0004 (9) |
C9 | 0.0287 (10) | 0.0276 (11) | 0.0316 (10) | −0.0002 (8) | 0.0041 (8) | 0.0053 (9) |
C10 | 0.0315 (10) | 0.0371 (12) | 0.0243 (9) | −0.0084 (10) | 0.0079 (8) | 0.0032 (9) |
C11 | 0.0268 (9) | 0.0333 (11) | 0.0259 (9) | −0.0052 (9) | 0.0109 (8) | −0.0031 (8) |
C12 | 0.0210 (8) | 0.0238 (10) | 0.0249 (9) | −0.0042 (8) | 0.0062 (7) | −0.0029 (8) |
C13 | 0.0271 (9) | 0.0267 (11) | 0.0347 (11) | 0.0029 (8) | 0.0100 (8) | −0.0027 (9) |
O2 | 0.0333 (7) | 0.0396 (10) | 0.0322 (7) | 0.0029 (7) | 0.0194 (6) | 0.0050 (7) |
N2 | 0.0239 (8) | 0.0236 (9) | 0.0222 (8) | 0.0019 (6) | 0.0103 (6) | 0.0011 (6) |
C15 | 0.0233 (8) | 0.0219 (10) | 0.0195 (8) | 0.0043 (8) | 0.0087 (7) | 0.0049 (8) |
C16 | 0.0249 (9) | 0.0228 (10) | 0.0240 (9) | −0.0013 (8) | 0.0073 (7) | 0.0026 (8) |
C17 | 0.0340 (10) | 0.0233 (10) | 0.0204 (9) | 0.0020 (8) | 0.0080 (8) | −0.0015 (8) |
C18 | 0.0298 (9) | 0.0305 (11) | 0.0238 (9) | 0.0036 (8) | 0.0139 (8) | 0.0014 (8) |
C19 | 0.0240 (9) | 0.0298 (11) | 0.0256 (9) | −0.0001 (8) | 0.0112 (8) | 0.0030 (8) |
C20 | 0.0249 (9) | 0.0190 (9) | 0.0206 (9) | 0.0010 (7) | 0.0071 (7) | 0.0039 (8) |
C21 | 0.0254 (9) | 0.0216 (10) | 0.0201 (8) | 0.0031 (8) | 0.0071 (7) | 0.0045 (8) |
C22 | 0.0278 (9) | 0.0257 (11) | 0.0233 (9) | −0.0016 (8) | 0.0076 (7) | 0.0035 (8) |
C23 | 0.0353 (11) | 0.0253 (11) | 0.0260 (10) | −0.0018 (9) | 0.0059 (8) | 0.0009 (8) |
C24 | 0.0398 (11) | 0.0260 (11) | 0.0209 (9) | 0.0051 (9) | 0.0079 (8) | −0.0012 (8) |
C25 | 0.0299 (9) | 0.0273 (11) | 0.0239 (9) | 0.0063 (8) | 0.0109 (8) | 0.0032 (8) |
C26 | 0.0246 (9) | 0.0207 (10) | 0.0194 (8) | 0.0031 (7) | 0.0063 (7) | 0.0043 (7) |
C27 | 0.0246 (9) | 0.0282 (11) | 0.0278 (9) | 0.0007 (8) | 0.0106 (8) | 0.0070 (8) |
O1—C13 | 1.212 (2) | O2—C27 | 1.213 (2) |
N1—C13 | 1.369 (3) | N2—C27 | 1.369 (2) |
N1—C12 | 1.412 (3) | N2—C26 | 1.413 (2) |
N1—C1 | 1.418 (2) | N2—C15 | 1.423 (2) |
C1—C2 | 1.394 (3) | C15—C16 | 1.385 (3) |
C1—C6 | 1.404 (3) | C15—C20 | 1.403 (3) |
C2—C3 | 1.383 (3) | C16—C17 | 1.390 (3) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.400 (3) | C17—C18 | 1.396 (3) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.386 (3) | C18—C19 | 1.389 (3) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.394 (3) | C19—C20 | 1.392 (3) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.456 (3) | C20—C21 | 1.452 (3) |
C7—C8 | 1.391 (3) | C21—C22 | 1.396 (3) |
C7—C12 | 1.410 (2) | C21—C26 | 1.409 (2) |
C8—C9 | 1.387 (3) | C22—C23 | 1.382 (3) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.400 (3) | C23—C24 | 1.398 (3) |
C9—H9 | 0.9300 | C23—H23 | 0.9300 |
C10—C11 | 1.387 (3) | C24—C25 | 1.386 (3) |
C10—H10 | 0.9300 | C24—H24 | 0.9300 |
C11—C12 | 1.394 (3) | C25—C26 | 1.394 (3) |
C11—H11 | 0.9300 | C25—H25 | 0.9300 |
C13—H13 | 0.9300 | C27—H27 | 0.9300 |
C13—N1—C12 | 127.14 (16) | C27—N2—C26 | 127.54 (16) |
C13—N1—C1 | 124.34 (17) | C27—N2—C15 | 123.73 (18) |
C12—N1—C1 | 108.47 (15) | C26—N2—C15 | 108.31 (15) |
C2—C1—C6 | 121.97 (17) | C16—C15—C20 | 122.73 (16) |
C2—C1—N1 | 129.53 (18) | C16—C15—N2 | 128.99 (17) |
C6—C1—N1 | 108.48 (17) | C20—C15—N2 | 108.27 (16) |
C3—C2—C1 | 117.48 (19) | C15—C16—C17 | 116.96 (17) |
C3—C2—H2 | 121.3 | C15—C16—H16 | 121.5 |
C1—C2—H2 | 121.3 | C17—C16—H16 | 121.5 |
C2—C3—C4 | 121.31 (19) | C16—C17—C18 | 121.40 (18) |
C2—C3—H3 | 119.3 | C16—C17—H17 | 119.3 |
C4—C3—H3 | 119.3 | C18—C17—H17 | 119.3 |
C5—C4—C3 | 120.90 (18) | C19—C18—C17 | 120.91 (17) |
C5—C4—H4 | 119.6 | C19—C18—H18 | 119.5 |
C3—C4—H4 | 119.6 | C17—C18—H18 | 119.5 |
C4—C5—C6 | 118.78 (19) | C18—C19—C20 | 118.70 (18) |
C4—C5—H5 | 120.6 | C18—C19—H19 | 120.6 |
C6—C5—H5 | 120.6 | C20—C19—H19 | 120.6 |
C5—C6—C1 | 119.56 (18) | C19—C20—C15 | 119.29 (18) |
C5—C6—C7 | 133.13 (19) | C19—C20—C21 | 133.13 (18) |
C1—C6—C7 | 107.31 (16) | C15—C20—C21 | 107.56 (15) |
C8—C7—C12 | 119.81 (18) | C22—C21—C26 | 119.50 (17) |
C8—C7—C6 | 132.74 (17) | C22—C21—C20 | 132.98 (16) |
C12—C7—C6 | 107.44 (17) | C26—C21—C20 | 107.51 (16) |
C9—C8—C7 | 118.89 (18) | C23—C22—C21 | 118.95 (17) |
C9—C8—H8 | 120.6 | C23—C22—H22 | 120.5 |
C7—C8—H8 | 120.6 | C21—C22—H22 | 120.5 |
C8—C9—C10 | 120.6 (2) | C22—C23—C24 | 120.72 (19) |
C8—C9—H9 | 119.7 | C22—C23—H23 | 119.6 |
C10—C9—H9 | 119.7 | C24—C23—H23 | 119.6 |
C11—C10—C9 | 121.61 (19) | C25—C24—C23 | 121.72 (19) |
C11—C10—H10 | 119.2 | C25—C24—H24 | 119.1 |
C9—C10—H10 | 119.2 | C23—C24—H24 | 119.1 |
C10—C11—C12 | 117.41 (19) | C24—C25—C26 | 117.21 (18) |
C10—C11—H11 | 121.3 | C24—C25—H25 | 121.4 |
C12—C11—H11 | 121.3 | C26—C25—H25 | 121.4 |
C11—C12—C7 | 121.65 (19) | C25—C26—C21 | 121.91 (18) |
C11—C12—N1 | 130.04 (18) | C25—C26—N2 | 129.73 (17) |
C7—C12—N1 | 108.30 (16) | C21—C26—N2 | 108.35 (15) |
O1—C13—N1 | 124.9 (2) | O2—C27—N2 | 124.9 (2) |
O1—C13—H13 | 117.6 | O2—C27—H27 | 117.6 |
N1—C13—H13 | 117.6 | N2—C27—H27 | 117.6 |
C13—N1—C1—C2 | 4.3 (3) | C27—N2—C15—C16 | 5.7 (3) |
C12—N1—C1—C2 | −178.30 (19) | C26—N2—C15—C16 | 178.78 (18) |
C13—N1—C1—C6 | −176.87 (18) | C27—N2—C15—C20 | −173.23 (16) |
C12—N1—C1—C6 | 0.5 (2) | C26—N2—C15—C20 | −0.1 (2) |
C6—C1—C2—C3 | 0.5 (3) | C20—C15—C16—C17 | 0.2 (3) |
N1—C1—C2—C3 | 179.17 (19) | N2—C15—C16—C17 | −178.55 (18) |
C1—C2—C3—C4 | −0.4 (3) | C15—C16—C17—C18 | 0.1 (3) |
C2—C3—C4—C5 | 0.2 (3) | C16—C17—C18—C19 | −0.5 (3) |
C3—C4—C5—C6 | −0.1 (3) | C17—C18—C19—C20 | 0.6 (3) |
C4—C5—C6—C1 | 0.2 (3) | C18—C19—C20—C15 | −0.3 (3) |
C4—C5—C6—C7 | −178.6 (2) | C18—C19—C20—C21 | 177.9 (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—C19 | 178.90 (16) |
C2—C1—C6—C7 | 178.65 (17) | C16—C15—C20—C21 | −178.76 (17) |
N1—C1—C6—C7 | −0.3 (2) | N2—C15—C20—C21 | 0.2 (2) |
C5—C6—C7—C8 | −0.3 (4) | C19—C20—C21—C22 | 2.6 (4) |
C1—C6—C7—C8 | −179.1 (2) | C15—C20—C21—C22 | −179.0 (2) |
C5—C6—C7—C12 | 178.8 (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—C9 | 178.5 (2) | C20—C21—C22—C23 | 178.5 (2) |
C7—C8—C9—C10 | 0.0 (3) | C21—C22—C23—C24 | 0.0 (3) |
C8—C9—C10—C11 | 0.4 (3) | C22—C23—C24—C25 | −0.1 (3) |
C9—C10—C11—C12 | −0.2 (3) | C23—C24—C25—C26 | 0.2 (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—C11 | 0.6 (3) | C22—C21—C26—C25 | 0.3 (3) |
C6—C7—C12—C11 | −178.60 (18) | C20—C21—C26—C25 | −178.64 (17) |
C8—C7—C12—N1 | 179.61 (16) | C22—C21—C26—N2 | 179.13 (16) |
C6—C7—C12—N1 | 0.4 (2) | C20—C21—C26—N2 | 0.2 (2) |
C13—N1—C12—C11 | −4.4 (3) | C27—N2—C26—C25 | −8.6 (3) |
C1—N1—C12—C11 | 178.3 (2) | C15—N2—C26—C25 | 178.65 (18) |
C13—N1—C12—C7 | 176.75 (18) | C27—N2—C26—C21 | 172.73 (18) |
C1—N1—C12—C7 | −0.6 (2) | C15—N2—C26—C21 | 0.0 (2) |
C12—N1—C13—O1 | −0.7 (3) | C26—N2—C27—O2 | 0.3 (3) |
C1—N1—C13—O1 | 176.17 (19) | C15—N2—C27—O2 | 172.09 (18) |
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−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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