3,4-Bis[1-(prop-2-yn­yl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione

Huang, M.-H.; Gao, Y.-C.; Yang, F.-L.; Luo, Y.-J.

doi:10.1107/S1600536813012889

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o924-o925

doi:10.1107/S1600536813012889

Open

access

3,4-Bis[1-(prop-2-ynyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione

Mu-Hua Huang,^a ^* Yong-Chen Gao,^b Feng-Ling Yang ^b and Yun-Jun Luo ^a

^aSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, People's Republic of China, and ^bDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: mhhuang@bit.edu.cn

(Received 30 April 2013; accepted 10 May 2013; online 18 May 2013)

In the title molecule, C₂₆H₁₇N₃O₂, both indole ring systems are essentially planar, with maximum deviations of 0.019 (2) and 0.033 (1) Å for the N atoms, and form dihedral angles of 34.40 (9) and 45.06 (8)° with the essentially planar pyrrole ring [maximum deviation = 0.020 (2) Å]. The dihedral angle between the two indole ring systems is 58.78 (6)°. In the crystal, molecules are connected by pairs of N—H⋯O hydrogen bonds, forming inversion dimers and generating R₂²(8) rings. Weak π–π stacking interactions, with a centroid–centroid distance of 3.983 (2) Å, are also observed.

Related literature

For the importance of bisindolylmaleimides in medicinal chemistry, see: Bulbule et al. (2008 ); Wang et al. (2012 ) and in materials science, see: Chiu et al. (2003 ); Kaletas et al. (2005 ); Lin et al. (2010 ); Nakazono et al. (2007 ); Yeh et al. (2006 ). For the isolation of bisindolylmaleimides from natural products, see: Kamata et al. (2006 ). For the synthesis of bisindolylmaleimides, see: Prateeptongkum et al. (2010 ). For a related crystal structure, see: Huang et al. (2012 ). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₁₇N₃O₂
M_r = 403.43
Triclinic, $[P \overline 1]$
a = 8.8015 (14) Å
b = 11.2619 (14) Å
c = 11.838 (3) Å
α = 62.860 (17)°
β = 73.625 (16)°
γ = 79.593 (12)°
V = 999.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 102 K
0.11 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.991, T_max = 0.994
6379 measured reflections
3920 independent reflections
3113 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.114
S = 1.03
3920 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.01	2.872 (2)	165
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813012889/lh5613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012889/lh5613Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012889/lh5613Isup3.cml

checkCIF report

Comment top

Bisindolylmaleimides are important in medicinal chemistry (Bulbule et al., 2008; Wang et al., 2012) and in the field of materials science (Chiu et al., 2003; Kaletas et al., 2005; Lin et al., 2010; Nakazono et al., 2007; Yeh et al., 2006). Bisindolylmaleimides have been isolated from natural products (Kamata et al., 2006). The synthesis of bisindolylmaleimides (Prateeptongkum et al., 2010) and an example of a related crystal structure (Huang et al., 2012) have been reported.

The molecular structure of the title compound is shown in Fig. 1. Both indole ring systems are essentially planar with maximum deviations of 0.019 (2)Å for N3 and 0.033 (1)Å for N2 and these ring systems form dihedral angles of 34.40 (9)Å [N3/C16-C23] and 45.06 (8)Å [N2/C5-C12] with the essentially planar pyrrole ring [N1/C1-C4] (maximum deviation 0.020 (2)Å for C1). The dihedral angle between the two indole ring systems is 58.78 (6)°. In the crystal, molecules are connected by pairs of N—H···O hydrogen bonds to form inversion dimers (Fig. 2) generating R²₂(8) rings (Bernstein et al., 1995). Weak π–π stacking interactions, with a Cg···Cg(2-x, 1-y, -z) distance of 3.983 (2)Å, are also observed [Cg is the centroid of the C18-C23 ring].

Related literature top

For the importance of bisindolylmaleimides in medicinal chemistry, see: Bulbule et al. (2008); Wang et al. (2012) and in materials science, see: Chiu et al. (2003); Kaletas et al. (2005); Lin et al. (2010); Nakazono et al. (2007); Yeh et al. (2006). For the isolation of bisindolylmaleimides from natural products, see: Kamata et al. (2006). For the synthesis of bisindolylmaleimides, see: Prateeptongkum et al. (2010). For a related crystal structure, see: Huang et al. (2012). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by N-alkylation of 3, 4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione by propargyl bromide with the aid of NaH freshly distilled THF under N₂ atmosphere. The reaction was initiated at 273K for 5 h. The reaction was quenched with sat. NH₄Cl at 273K, extracted with EtOAc, dried over anhydrous Na₂SO₄ and concentrated in vacuo. The residue was purified by f.c.c.(silica gel, eluted with 14% EtOAc in Petroleum Ether) to give the title compound in a yield of 83%, which provided the sample suitable for X-ray analysis after natural evaporation of solvents.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A portion of the crystal packing viewed approximately along the a axis. The dashed lines indicate N—H···O hydrogen bonds.

3,4-Bis[1-(prop-2-ynyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione top

Crystal data top

C₂₆H₁₇N₃O₂	V = 999.9 (3) Å³
M_r = 403.43	Z = 2
Triclinic, P1	F(000) = 420
Hall symbol: -P 1	D_x = 1.340 Mg m⁻³
a = 8.8015 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2619 (14) Å	θ = 1.5–51.8°
c = 11.838 (3) Å	µ = 0.09 mm⁻¹
α = 62.860 (17)°	T = 102 K
β = 73.625 (16)°	Block, colorless
γ = 79.593 (12)°	0.11 × 0.10 × 0.07 mm

Data collection top

Bruker SMART CCD diffractometer	3920 independent reflections
Radiation source: fine-focus sealed tube	3113 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.0°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→9
T_min = 0.991, T_max = 0.994	k = −13→13
6379 measured reflections	l = −11→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0438P)² + 0.3377P] where P = (F_o² + 2F_c²)/3
3920 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₆H₁₇N₃O₂	γ = 79.593 (12)°
M_r = 403.43	V = 999.9 (3) Å³
Triclinic, P1	Z = 2
a = 8.8015 (14) Å	Mo Kα radiation
b = 11.2619 (14) Å	µ = 0.09 mm⁻¹
c = 11.838 (3) Å	T = 102 K
α = 62.860 (17)°	0.11 × 0.10 × 0.07 mm
β = 73.625 (16)°

Data collection top

Bruker SMART CCD diffractometer	3920 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3113 reflections with I > 2σ(I)
T_min = 0.991, T_max = 0.994	R_int = 0.024
6379 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 0.37 e Å⁻³
3920 reflections	Δρ_min = −0.23 e Å⁻³
280 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O2	0.33248 (15)	0.75325 (12)	0.29355 (12)	0.0242 (3)
O1	0.11940 (15)	0.34749 (12)	0.48806 (13)	0.0248 (3)
C12	0.7380 (2)	0.27334 (17)	0.39074 (16)	0.0203 (4)
H12	0.7278	0.3531	0.4017	0.024*
C20	0.8983 (2)	0.62081 (19)	−0.09736 (18)	0.0259 (4)
H20	0.9790	0.6819	−0.1502	0.031*
C19	0.7956 (2)	0.62914 (17)	0.01340 (17)	0.0200 (4)
N2	0.48798 (18)	0.09433 (14)	0.33954 (14)	0.0202 (3)
C18	0.6728 (2)	0.54223 (17)	0.09277 (17)	0.0185 (4)
C23	0.6555 (2)	0.44154 (18)	0.05835 (18)	0.0239 (4)
H23	0.5741	0.3807	0.1093	0.029*
N3	0.79109 (19)	0.71857 (15)	0.06452 (15)	0.0253 (4)
C17	0.5904 (2)	0.58517 (17)	0.19368 (17)	0.0205 (4)
C7	0.6120 (2)	0.23464 (17)	0.36673 (16)	0.0180 (4)
C9	0.7717 (2)	0.03492 (18)	0.35768 (18)	0.0245 (4)
H9	0.7834	−0.0443	0.3456	0.029*
C14	0.5187 (2)	0.04567 (18)	0.15627 (19)	0.0250 (4)
C16	0.6670 (2)	0.69296 (18)	0.17015 (19)	0.0260 (4)
H16	0.6375	0.7427	0.2206	0.031*
C13	0.4647 (2)	−0.00393 (18)	0.29867 (18)	0.0247 (4)
H13A	0.3508	−0.0218	0.3255	0.030*
H13B	0.5249	−0.0889	0.3418	0.030*
C8	0.6308 (2)	0.11411 (17)	0.35377 (16)	0.0194 (4)
C4	0.3246 (2)	0.63429 (17)	0.32913 (17)	0.0201 (4)
C22	0.7586 (2)	0.4323 (2)	−0.05068 (19)	0.0287 (5)
H22	0.7475	0.3643	−0.0737	0.034*
C11	0.8770 (2)	0.19342 (19)	0.39814 (17)	0.0250 (4)
H11	0.9624	0.2179	0.4158	0.030*
C5	0.3823 (2)	0.19972 (17)	0.34038 (17)	0.0201 (4)
H5	0.2763	0.2098	0.3312	0.024*
N1	0.19290 (18)	0.56262 (14)	0.41135 (15)	0.0228 (4)
H1	0.1059	0.5957	0.4484	0.027*
C10	0.8942 (2)	0.07670 (19)	0.37999 (18)	0.0271 (4)
H10	0.9923	0.0251	0.3831	0.033*
C2	0.3827 (2)	0.41642 (17)	0.35429 (17)	0.0178 (4)
C15	0.5634 (3)	0.09309 (19)	0.0417 (2)	0.0320 (5)
H15	0.5993	0.1313	−0.0505	0.038*
C6	0.4527 (2)	0.28858 (17)	0.35655 (16)	0.0181 (4)
C3	0.4463 (2)	0.53771 (17)	0.29249 (17)	0.0189 (4)
C21	0.8777 (2)	0.5207 (2)	−0.12664 (18)	0.0291 (5)
H21	0.9466	0.5118	−0.2006	0.035*
C25	0.9581 (2)	0.83373 (18)	0.1088 (2)	0.0277 (5)
C1	0.2178 (2)	0.43211 (17)	0.42665 (17)	0.0198 (4)
C24	0.8937 (3)	0.8296 (2)	0.0096 (2)	0.0328 (5)
H24A	0.8322	0.9148	−0.0306	0.039*
H24B	0.9822	0.8204	−0.0598	0.039*
C26	1.0093 (3)	0.83789 (19)	0.1887 (2)	0.0344 (5)
H26	1.0506	0.8413	0.2531	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0229 (8)	0.0190 (7)	0.0286 (7)	−0.0038 (5)	−0.0003 (6)	−0.0108 (6)
O1	0.0188 (7)	0.0217 (7)	0.0301 (7)	−0.0056 (5)	0.0049 (6)	−0.0124 (6)
C12	0.0228 (10)	0.0222 (9)	0.0144 (8)	−0.0046 (7)	−0.0031 (7)	−0.0062 (8)
C20	0.0177 (10)	0.0301 (11)	0.0183 (9)	−0.0005 (8)	−0.0007 (8)	−0.0027 (9)
C19	0.0159 (10)	0.0201 (9)	0.0194 (9)	0.0026 (7)	−0.0061 (7)	−0.0046 (8)
N2	0.0214 (9)	0.0190 (8)	0.0198 (8)	−0.0028 (6)	−0.0025 (6)	−0.0088 (7)
C18	0.0136 (9)	0.0201 (9)	0.0162 (9)	0.0001 (7)	−0.0044 (7)	−0.0029 (8)
C23	0.0204 (10)	0.0291 (10)	0.0203 (9)	−0.0001 (8)	−0.0058 (8)	−0.0088 (8)
N3	0.0210 (9)	0.0246 (9)	0.0238 (8)	−0.0074 (6)	0.0013 (7)	−0.0065 (7)
C17	0.0157 (10)	0.0184 (9)	0.0221 (9)	−0.0007 (7)	−0.0010 (7)	−0.0064 (8)
C7	0.0184 (10)	0.0197 (9)	0.0114 (8)	−0.0020 (7)	−0.0003 (7)	−0.0043 (7)
C9	0.0269 (11)	0.0213 (10)	0.0193 (9)	0.0018 (8)	−0.0027 (8)	−0.0063 (8)
C14	0.0304 (11)	0.0198 (10)	0.0279 (11)	−0.0038 (8)	−0.0065 (9)	−0.0120 (9)
C16	0.0244 (11)	0.0236 (10)	0.0263 (10)	−0.0048 (8)	0.0023 (8)	−0.0110 (9)
C13	0.0310 (12)	0.0204 (10)	0.0247 (10)	−0.0053 (8)	−0.0044 (9)	−0.0110 (8)
C8	0.0213 (10)	0.0196 (9)	0.0138 (8)	−0.0031 (7)	−0.0021 (7)	−0.0045 (7)
C4	0.0183 (10)	0.0212 (10)	0.0195 (9)	−0.0049 (7)	−0.0012 (7)	−0.0082 (8)
C22	0.0279 (12)	0.0329 (11)	0.0241 (10)	0.0027 (8)	−0.0087 (9)	−0.0112 (9)
C11	0.0198 (10)	0.0327 (11)	0.0170 (9)	−0.0050 (8)	−0.0048 (8)	−0.0043 (8)
C5	0.0166 (10)	0.0211 (9)	0.0187 (9)	−0.0035 (7)	0.0005 (7)	−0.0070 (8)
N1	0.0174 (8)	0.0203 (8)	0.0274 (8)	−0.0028 (6)	0.0058 (7)	−0.0133 (7)
C10	0.0211 (11)	0.0293 (11)	0.0211 (10)	0.0048 (8)	−0.0042 (8)	−0.0052 (9)
C2	0.0149 (9)	0.0219 (9)	0.0171 (9)	−0.0024 (7)	−0.0017 (7)	−0.0093 (8)
C15	0.0466 (14)	0.0262 (11)	0.0252 (11)	−0.0083 (9)	−0.0066 (10)	−0.0114 (9)
C6	0.0178 (10)	0.0188 (9)	0.0147 (8)	−0.0031 (7)	0.0013 (7)	−0.0069 (7)
C3	0.0172 (10)	0.0205 (9)	0.0185 (9)	−0.0009 (7)	−0.0015 (7)	−0.0094 (8)
C21	0.0249 (11)	0.0393 (12)	0.0197 (10)	0.0076 (9)	−0.0048 (8)	−0.0135 (9)
C25	0.0206 (11)	0.0220 (10)	0.0340 (11)	−0.0060 (8)	0.0004 (9)	−0.0088 (9)
C1	0.0190 (10)	0.0199 (9)	0.0201 (9)	−0.0036 (7)	−0.0004 (8)	−0.0099 (8)
C24	0.0291 (12)	0.0299 (11)	0.0305 (11)	−0.0137 (9)	0.0008 (9)	−0.0055 (9)
C26	0.0323 (13)	0.0262 (11)	0.0406 (13)	−0.0017 (9)	−0.0068 (10)	−0.0118 (10)

Geometric parameters (Å, º) top

O2—C4	1.216 (2)	C14—C15	1.180 (3)
O1—C1	1.224 (2)	C14—C13	1.471 (3)
C12—C11	1.380 (3)	C16—H16	0.9500
C12—C7	1.402 (2)	C13—H13A	0.9900
C12—H12	0.9500	C13—H13B	0.9900
C20—C21	1.375 (3)	C4—N1	1.388 (2)
C20—C19	1.399 (3)	C4—C3	1.506 (2)
C20—H20	0.9500	C22—C21	1.388 (3)
C19—N3	1.382 (2)	C22—H22	0.9500
C19—C18	1.407 (2)	C11—C10	1.402 (3)
N2—C5	1.371 (2)	C11—H11	0.9500
N2—C8	1.383 (2)	C5—C6	1.374 (2)
N2—C13	1.459 (2)	C5—H5	0.9500
C18—C23	1.412 (3)	N1—C1	1.380 (2)
C18—C17	1.449 (3)	N1—H1	0.8800
C23—C22	1.389 (3)	C10—H10	0.9500
C23—H23	0.9500	C2—C3	1.359 (2)
N3—C16	1.362 (2)	C2—C6	1.451 (2)
N3—C24	1.462 (2)	C2—C1	1.489 (2)
C17—C16	1.374 (2)	C15—H15	0.9500
C17—C3	1.449 (2)	C21—H21	0.9500
C7—C8	1.410 (2)	C25—C26	1.178 (3)
C7—C6	1.439 (2)	C25—C24	1.463 (3)
C9—C10	1.382 (3)	C24—H24A	0.9900
C9—C8	1.390 (3)	C24—H24B	0.9900
C9—H9	0.9500	C26—H26	0.9500

C11—C12—C7	118.76 (17)	O2—C4—N1	124.49 (17)
C11—C12—H12	120.6	O2—C4—C3	128.73 (16)
C7—C12—H12	120.6	N1—C4—C3	106.75 (14)
C21—C20—C19	117.34 (18)	C21—C22—C23	121.13 (19)
C21—C20—H20	121.3	C21—C22—H22	119.4
C19—C20—H20	121.3	C23—C22—H22	119.4
N3—C19—C20	129.06 (17)	C12—C11—C10	121.12 (18)
N3—C19—C18	107.88 (16)	C12—C11—H11	119.4
C20—C19—C18	123.06 (17)	C10—C11—H11	119.4
C5—N2—C8	109.07 (14)	N2—C5—C6	109.78 (16)
C5—N2—C13	124.26 (16)	N2—C5—H5	125.1
C8—N2—C13	125.14 (15)	C6—C5—H5	125.1
C19—C18—C23	117.57 (16)	C1—N1—C4	110.35 (15)
C19—C18—C17	106.66 (15)	C1—N1—H1	124.8
C23—C18—C17	135.75 (17)	C4—N1—H1	124.8
C22—C23—C18	119.34 (18)	C9—C10—C11	121.56 (18)
C22—C23—H23	120.3	C9—C10—H10	119.2
C18—C23—H23	120.3	C11—C10—H10	119.2
C16—N3—C19	108.84 (15)	C3—C2—C6	129.71 (17)
C16—N3—C24	124.81 (16)	C3—C2—C1	108.11 (15)
C19—N3—C24	126.19 (16)	C6—C2—C1	122.18 (15)
C16—C17—C18	106.03 (16)	C14—C15—H15	180.0
C16—C17—C3	124.76 (17)	C5—C6—C7	106.70 (15)
C18—C17—C3	128.89 (16)	C5—C6—C2	126.26 (17)
C12—C7—C8	118.80 (17)	C7—C6—C2	126.90 (15)
C12—C7—C6	134.27 (16)	C2—C3—C17	131.66 (16)
C8—C7—C6	106.86 (15)	C2—C3—C4	107.35 (15)
C10—C9—C8	116.94 (17)	C17—C3—C4	120.44 (15)
C10—C9—H9	121.5	C20—C21—C22	121.54 (19)
C8—C9—H9	121.5	C20—C21—H21	119.2
C15—C14—C13	175.8 (2)	C22—C21—H21	119.2
N3—C16—C17	110.56 (17)	C26—C25—C24	179.5 (2)
N3—C16—H16	124.7	O1—C1—N1	125.03 (17)
C17—C16—H16	124.7	O1—C1—C2	127.66 (16)
N2—C13—C14	110.29 (15)	N1—C1—C2	107.30 (14)
N2—C13—H13A	109.6	N3—C24—C25	111.76 (16)
C14—C13—H13A	109.6	N3—C24—H24A	109.3
N2—C13—H13B	109.6	C25—C24—H24A	109.3
C14—C13—H13B	109.6	N3—C24—H24B	109.3
H13A—C13—H13B	108.1	C25—C24—H24B	109.3
N2—C8—C9	129.68 (17)	H24A—C24—H24B	107.9
N2—C8—C7	107.57 (16)	C25—C26—H26	180.0
C9—C8—C7	122.74 (17)

C21—C20—C19—N3	179.63 (18)	C13—N2—C5—C6	−167.15 (15)
C21—C20—C19—C18	−1.3 (3)	O2—C4—N1—C1	176.33 (18)
N3—C19—C18—C23	−179.89 (15)	C3—C4—N1—C1	−1.9 (2)
C20—C19—C18—C23	0.8 (3)	C8—C9—C10—C11	0.1 (3)
N3—C19—C18—C17	1.25 (19)	C12—C11—C10—C9	−1.8 (3)
C20—C19—C18—C17	−178.03 (16)	N2—C5—C6—C7	−0.17 (19)
C19—C18—C23—C22	0.0 (3)	N2—C5—C6—C2	175.86 (16)
C17—C18—C23—C22	178.43 (19)	C12—C7—C6—C5	−175.92 (18)
C20—C19—N3—C16	177.35 (18)	C8—C7—C6—C5	0.94 (19)
C18—C19—N3—C16	−1.9 (2)	C12—C7—C6—C2	8.1 (3)
C20—C19—N3—C24	1.8 (3)	C8—C7—C6—C2	−175.05 (16)
C18—C19—N3—C24	−177.39 (17)	C3—C2—C6—C5	−134.3 (2)
C19—C18—C17—C16	−0.2 (2)	C1—C2—C6—C5	46.1 (3)
C23—C18—C17—C16	−178.7 (2)	C3—C2—C6—C7	40.9 (3)
C19—C18—C17—C3	173.55 (18)	C1—C2—C6—C7	−138.68 (18)
C23—C18—C17—C3	−5.0 (3)	C6—C2—C3—C17	11.6 (3)
C11—C12—C7—C8	1.3 (2)	C1—C2—C3—C17	−168.76 (19)
C11—C12—C7—C6	177.89 (18)	C6—C2—C3—C4	−177.07 (17)
C19—N3—C16—C17	1.8 (2)	C1—C2—C3—C4	2.5 (2)
C24—N3—C16—C17	177.39 (17)	C16—C17—C3—C2	−157.5 (2)
C18—C17—C16—N3	−1.0 (2)	C18—C17—C3—C2	29.8 (3)
C3—C17—C16—N3	−175.05 (17)	C16—C17—C3—C4	32.1 (3)
C5—N2—C13—C14	84.9 (2)	C18—C17—C3—C4	−140.54 (18)
C8—N2—C13—C14	−79.4 (2)	O2—C4—C3—C2	−178.66 (18)
C5—N2—C8—C9	−179.60 (18)	N1—C4—C3—C2	−0.5 (2)
C13—N2—C8—C9	−13.3 (3)	O2—C4—C3—C17	−6.2 (3)
C5—N2—C8—C7	1.29 (19)	N1—C4—C3—C17	171.94 (16)
C13—N2—C8—C7	167.59 (15)	C19—C20—C21—C22	0.9 (3)
C10—C9—C8—N2	−176.65 (17)	C23—C22—C21—C20	−0.1 (3)
C10—C9—C8—C7	2.4 (3)	C4—N1—C1—O1	−175.96 (18)
C12—C7—C8—N2	176.07 (15)	C4—N1—C1—C2	3.4 (2)
C6—C7—C8—N2	−1.36 (19)	C3—C2—C1—O1	175.62 (18)
C12—C7—C8—C9	−3.1 (3)	C6—C2—C1—O1	−4.7 (3)
C6—C7—C8—C9	179.45 (16)	C3—C2—C1—N1	−3.8 (2)
C18—C23—C22—C21	−0.3 (3)	C6—C2—C1—N1	175.90 (16)
C7—C12—C11—C10	1.1 (3)	C16—N3—C24—C25	52.3 (3)
C8—N2—C5—C6	−0.7 (2)	C19—N3—C24—C25	−132.89 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.01	2.872 (2)	165

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₇N₃O₂
M_r	403.43
Crystal system, space group	Triclinic, P1
Temperature (K)	102
a, b, c (Å)	8.8015 (14), 11.2619 (14), 11.838 (3)
α, β, γ (°)	62.860 (17), 73.625 (16), 79.593 (12)
V (Å³)	999.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.11 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.991, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	6379, 3920, 3113
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.114, 1.03
No. of reflections	3920
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.23

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.01	2.872 (2)	165.4

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors wish to thank the Natural Science Foundation of China (No. 21202008) for generous support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bulbule, V. J., Rivas, K., Verlinde, C. L. M. J., Van Voorhis, W. C. & Gelb, M. H. (2008). J. Med. Chem. 51, 384–387. Web of Science CrossRef PubMed CAS Google Scholar
Chiu, C.-W., Chow, T.-J., Chuen, C.-H., Lin, H.-M. & Tao, Y.-T. (2003). Chem. Mater. 15, 4527–4532. Web of Science CSD CrossRef CAS Google Scholar
Huang, L., Li, Y., Gao, D. & Du, Z. (2012). Acta Cryst. E68, o1328. CSD CrossRef IUCr Journals Google Scholar
Kaletas, B. K., Kozhevnikov, V. N., Zimine, M., Williams, R. M., Koenig, B. & De Cola, L. (2005). Eur. J. Org. Chem. pp. 3443–3449. Google Scholar
Kamata, K., Suetsugu, T., Yamamoto, Y., Hayashi, M., Komiyama, K. & Ishibashi, M. (2006). J. Nat. Prod. 69, 1252–1254. Web of Science CrossRef PubMed CAS Google Scholar
Lin, Z., Lin, Y.-D., Wu, C.-Y., Chow, P.-T., Sun, C.-H. & Chow, T. J. (2010). Macromolecules, 43, 5925–5931. Web of Science CrossRef CAS Google Scholar
Nakazono, M., Nanbu, S., Uesaki, A., Kuwano, R., Kashiwabara, M. & Zaitsu, K. (2007). Org. Lett. 9, 3583–3586. Web of Science CrossRef PubMed CAS Google Scholar
Prateeptongkum, S., Driller, K. M., Jackstell, R., Spannenberg, A. & Beller, M. (2010). Chem. Eur. J. 16, 9606–9615. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, K., Yan, Z., Wang, N. & Liu, Z. Z. (2012). Chin. Chem. Lett. 23, 462–465. Web of Science CrossRef CAS Google Scholar
Yeh, T.-S., Chow, T. J., Tsai, S.-H., Chiu, C.-W. & Zhao, C.-X. (2006). Chem. Mater. 18, 832–839. Web of Science CrossRef CAS Google Scholar