3,3-Bis(1H-indol-3-yl)indolin-2-one

Selvanayagam, S.; Chandak, M.S.; Velmurugan, D.; Ravikumar, K.; Raghunathan, R.

doi:10.1107/S1600536805027248

3,3-Bis(1H-indol-3-yl)indolin-2-one

S. Selvanayagam, M. S. Chandak, D. Velmurugan, K. Ravikumar and R. Raghunathan

In the title compound, C₂₄H₁₇N₃O, the dihedral angles between the planes of the two indole ring systems and the oxindole group are 77.7 (1) and 71.9 (1)°. The molecular packing in the crystal structure is stabilized by an intermolecular N—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027248/bt6707sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027248/bt6707Isup2.hkl Contains datablock I

CCDC reference: 287459

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.050
wR factor = 0.134
Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3     ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Indole, being an integral part of many natural products of therapeutic importance, possesses potentially reactive sites for a variety of chemical reactions to generate molecular diversity (Farhanullah et al., 2004). Indole derivatives are identified as interfering with a G protein-independent signaling pathway of CRTH2 receptor (Mathiesen et al., 2005). These derivatives also possess antiviral (Sechi et al., 2004) and antimalarial (Agarwal et al., 2005) activities. Oxindole derivatives possess antifungal activity (Strigacova et al., 2001) and act as orally active potent growth hormone secretagogues (Tokunaga et al., 2001). In view of its importance and to obtain more detailed information about the structural conformation of the molecule, the structure of the title compound, (I), was determined.

Compound (I) (Fig. 1) consists of two indole groups (A and B) and one oxindole group (C). Selected geometric parameters are presented in Table 1. The geometry of the indole rings is comparable to those reported for other indole derivatives (Karthick et al., 2005; Sonar et al., 2005).

The two indole rign systems are oriented with a dihedral angle of 68.4 (1)° with respect to each other. The dihedral angles between the oxindole plane and the indole planes (A and B) are 77.7 (1) and 71.9 (1)°, respectively.

In the crystal structure, two inversion-related molecules are linked via an N1—H1···O1ⁱ hydrogen bond (Table 2). As a result, an R²₂(14) graph-set dimer is formed.

Experimental top

A mixture of indole (2.5 mmol), isatin (1.25 mmol) and gadolinium trifluoromethanesulfonate (55 mg, 0.093 mmol) was stirred in acetonitrile (6 ml). After completion of the reaction, water was added to quench the reaction, and the product was extracted with ethylacetate (3 × 10 ml) and washed with aqueous sodium bicarbonate and a sodium chloride solution; the combined organic layers were dried using anhydrous Na₂SO₄ and filtered, and the solvent was evaporated. The crude products were purified by column chromatography and eluted with an ethylacetate and hexane (3:1) mixture to afford the title compound. To obtain diffraction quality crystals, recrystallization was carried out using an ethylacetate and hexane (1:1) mixture.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top

Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

3,3-Bis(1H-indol-3-yl)indolin-2-one top

Crystal data top

C₂₄H₁₇N₃O	F(000) = 1520
M_r = 363.41	D_x = 1.332 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9828 reflections
a = 24.0578 (12) Å	θ = 2.5–26.6°
b = 10.2342 (5) Å	µ = 0.08 mm⁻¹
c = 18.1597 (9) Å	T = 293 K
β = 125.861 (1)°	Block, colourless
V = 3623.6 (3) Å³	0.24 × 0.22 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX area-detector diffractometer	3677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
ω scans	h = −31→31
20359 measured reflections	k = −13→13
4278 independent reflections	l = −23→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0696P)² + 1.847P] where P = (F_o² + 2F_c²)/3
4278 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₁₇N₃O	V = 3623.6 (3) Å³
M_r = 363.41	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.0578 (12) Å	µ = 0.08 mm⁻¹
b = 10.2342 (5) Å	T = 293 K
c = 18.1597 (9) Å	0.24 × 0.22 × 0.20 mm
β = 125.861 (1)°

Data collection top

Bruker SMART APEX area-detector diffractometer	3677 reflections with I > 2σ(I)
20359 measured reflections	R_int = 0.023
4278 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
4278 reflections	Δρ_min = −0.22 e Å⁻³
253 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
O1	0.36680 (6)	0.34810 (10)	0.47802 (8)	0.0527 (3)
N1	0.19426 (7)	0.10835 (13)	0.42508 (9)	0.0478 (3)
H1	0.1786	0.1034	0.4572	0.057*
N2	0.49456 (7)	−0.01347 (15)	0.60660 (10)	0.0585 (4)
H2	0.5370	−0.0108	0.6522	0.070*
N3	0.35915 (7)	0.31588 (11)	0.34777 (9)	0.0442 (3)
H3	0.3673	0.3948	0.3404	0.053*
C1	0.15557 (8)	0.11366 (14)	0.33255 (11)	0.0421 (3)
C2	0.08467 (9)	0.11248 (19)	0.26935 (14)	0.0606 (5)
H2A	0.0560	0.1068	0.2880	0.073*
C3	0.05800 (9)	0.11981 (18)	0.17889 (14)	0.0613 (5)
H3A	0.0107	0.1180	0.1356	0.074*
C4	0.10087 (8)	0.12999 (15)	0.15087 (11)	0.0497 (4)
H4	0.0816	0.1363	0.0892	0.060*
C5	0.17132 (7)	0.13091 (13)	0.21295 (10)	0.0382 (3)
H5	0.1992	0.1380	0.1933	0.046*
C6	0.20042 (7)	0.12108 (12)	0.30600 (10)	0.0335 (3)
C7	0.26870 (7)	0.11893 (12)	0.38898 (9)	0.0320 (3)
C8	0.26183 (8)	0.11228 (14)	0.45823 (10)	0.0397 (3)
H8	0.2982	0.1106	0.5196	0.048*
C9	0.45245 (8)	−0.11961 (16)	0.58086 (10)	0.0454 (4)
C10	0.46520 (9)	−0.24451 (19)	0.61847 (12)	0.0602 (5)
H10	0.5083	−0.2671	0.6698	0.072*
C11	0.41269 (10)	−0.33243 (18)	0.57782 (13)	0.0598 (5)
H11	0.4203	−0.4164	0.6015	0.072*
C12	0.34805 (9)	−0.29896 (15)	0.50172 (12)	0.0517 (4)
H12	0.3131	−0.3607	0.4756	0.062*
C13	0.33481 (7)	−0.17591 (14)	0.46412 (9)	0.0393 (3)
H13	0.2913	−0.1548	0.4131	0.047*
C14	0.38741 (7)	−0.08311 (13)	0.50346 (9)	0.0344 (3)
C15	0.39265 (7)	0.05122 (13)	0.48435 (9)	0.0343 (3)
C16	0.45856 (8)	0.08765 (17)	0.54850 (11)	0.0502 (4)
H16	0.4766	0.1698	0.5523	0.060*
C17	0.33740 (7)	0.13018 (12)	0.40370 (9)	0.0316 (3)
C18	0.35667 (7)	0.27795 (13)	0.41715 (10)	0.0379 (3)
C19	0.34700 (7)	0.21277 (13)	0.28932 (9)	0.0358 (3)
C20	0.34793 (8)	0.21436 (16)	0.21404 (10)	0.0459 (4)
H20	0.3555	0.2913	0.1939	0.055*
C21	0.33709 (9)	0.09674 (17)	0.16975 (11)	0.0508 (4)
H21	0.3378	0.0945	0.1192	0.061*
C22	0.32518 (9)	−0.01725 (16)	0.19913 (10)	0.0475 (4)
H22	0.3181	−0.0950	0.1683	0.057*
C23	0.32362 (7)	−0.01674 (13)	0.27478 (9)	0.0380 (3)
H23	0.3154	−0.0934	0.2945	0.046*
C24	0.33440 (6)	0.09928 (13)	0.31944 (9)	0.0315 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0733 (8)	0.0406 (6)	0.0699 (7)	−0.0152 (5)	0.0562 (7)	−0.0197 (5)
N1	0.0508 (7)	0.0574 (8)	0.0560 (8)	0.0045 (6)	0.0429 (7)	0.0089 (6)
N2	0.0322 (6)	0.0699 (10)	0.0507 (8)	−0.0035 (6)	0.0116 (6)	0.0013 (7)
N3	0.0614 (8)	0.0298 (6)	0.0571 (8)	−0.0066 (5)	0.0435 (7)	−0.0011 (5)
C1	0.0430 (8)	0.0380 (7)	0.0562 (9)	0.0056 (6)	0.0352 (7)	0.0106 (6)
C2	0.0409 (8)	0.0711 (12)	0.0782 (12)	0.0112 (8)	0.0396 (9)	0.0283 (9)
C3	0.0344 (8)	0.0641 (11)	0.0722 (12)	0.0063 (7)	0.0238 (8)	0.0257 (9)
C4	0.0457 (8)	0.0438 (8)	0.0481 (9)	0.0040 (6)	0.0211 (7)	0.0111 (7)
C5	0.0413 (7)	0.0319 (7)	0.0434 (7)	0.0018 (5)	0.0261 (6)	0.0046 (5)
C6	0.0367 (7)	0.0245 (6)	0.0454 (7)	0.0021 (5)	0.0275 (6)	0.0034 (5)
C7	0.0378 (7)	0.0278 (6)	0.0384 (7)	0.0003 (5)	0.0267 (6)	0.0003 (5)
C8	0.0444 (8)	0.0421 (7)	0.0429 (7)	0.0010 (6)	0.0313 (7)	0.0020 (6)
C9	0.0359 (7)	0.0550 (9)	0.0412 (8)	0.0031 (6)	0.0203 (6)	0.0014 (6)
C10	0.0514 (10)	0.0661 (11)	0.0518 (9)	0.0200 (8)	0.0238 (8)	0.0194 (8)
C11	0.0693 (11)	0.0463 (9)	0.0615 (10)	0.0119 (8)	0.0370 (9)	0.0174 (8)
C12	0.0606 (10)	0.0407 (8)	0.0540 (9)	−0.0035 (7)	0.0337 (8)	0.0025 (7)
C13	0.0417 (7)	0.0389 (7)	0.0357 (7)	−0.0023 (6)	0.0218 (6)	−0.0006 (6)
C14	0.0356 (6)	0.0393 (7)	0.0314 (6)	0.0023 (5)	0.0214 (5)	−0.0001 (5)
C15	0.0346 (6)	0.0379 (7)	0.0350 (6)	−0.0040 (5)	0.0230 (6)	−0.0044 (5)
C16	0.0413 (8)	0.0510 (9)	0.0538 (9)	−0.0109 (7)	0.0254 (7)	−0.0071 (7)
C17	0.0380 (7)	0.0287 (6)	0.0368 (6)	−0.0031 (5)	0.0267 (6)	−0.0034 (5)
C18	0.0420 (7)	0.0331 (7)	0.0497 (8)	−0.0044 (5)	0.0331 (7)	−0.0051 (6)
C19	0.0364 (7)	0.0354 (7)	0.0413 (7)	0.0000 (5)	0.0259 (6)	0.0017 (5)
C20	0.0520 (9)	0.0499 (9)	0.0449 (8)	−0.0039 (7)	0.0335 (7)	0.0070 (7)
C21	0.0599 (10)	0.0642 (10)	0.0396 (8)	−0.0024 (8)	0.0355 (8)	−0.0010 (7)
C22	0.0598 (9)	0.0480 (9)	0.0424 (8)	−0.0019 (7)	0.0343 (7)	−0.0089 (6)
C23	0.0451 (7)	0.0347 (7)	0.0399 (7)	−0.0002 (5)	0.0281 (6)	−0.0004 (5)
C24	0.0311 (6)	0.0350 (6)	0.0339 (6)	0.0010 (5)	0.0221 (5)	0.0013 (5)

Geometric parameters (Å, º) top

O1—C18	1.217 (2)	C9—C14	1.4096 (19)
N1—C1	1.364 (2)	C10—C11	1.363 (3)
N1—C8	1.3637 (19)	C10—H10	0.9300
N1—H1	0.8600	C11—C12	1.388 (3)
N2—C16	1.365 (2)	C11—H11	0.9300
N2—C9	1.367 (2)	C12—C13	1.378 (2)
N2—H2	0.8600	C12—H12	0.9300
N3—C18	1.3526 (18)	C13—C14	1.3980 (19)
N3—C19	1.4007 (18)	C13—H13	0.9300
N3—H3	0.8600	C14—C15	1.4415 (19)
C1—C2	1.390 (2)	C15—C16	1.359 (2)
C1—C6	1.4186 (19)	C15—C17	1.511 (2)
C2—C3	1.372 (3)	C16—H16	0.9300
C2—H2A	0.9300	C17—C24	1.5221 (17)
C3—C4	1.396 (3)	C17—C18	1.5585 (18)
C3—H3A	0.9300	C19—C20	1.380 (2)
C4—C5	1.380 (2)	C19—C24	1.3909 (18)
C4—H4	0.9300	C20—C21	1.385 (2)
C5—C6	1.403 (2)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.381 (2)
C6—C7	1.4384 (19)	C21—H21	0.9300
C7—C8	1.3628 (18)	C22—C23	1.3961 (19)
C7—C17	1.516 (2)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.3743 (18)
C9—C10	1.396 (2)	C23—H23	0.9300

C1—N1—C8	108.63 (12)	C13—C12—C11	121.18 (16)
C1—N1—H1	125.7	C13—C12—H12	119.4
C8—N1—H1	125.7	C11—C12—H12	119.4
C16—N2—C9	109.30 (13)	C12—C13—C14	119.37 (14)
C16—N2—H2	125.4	C12—C13—H13	120.3
C9—N2—H2	125.4	C14—C13—H13	120.3
C18—N3—C19	112.72 (11)	C13—C14—C9	118.25 (13)
C18—N3—H3	123.6	C13—C14—C15	134.88 (13)
C19—N3—H3	123.6	C9—C14—C15	106.87 (12)
N1—C1—C2	129.67 (15)	C16—C15—C14	106.15 (13)
N1—C1—C6	108.35 (13)	C16—C15—C17	127.32 (13)
C2—C1—C6	121.98 (15)	C14—C15—C17	126.29 (11)
C3—C2—C1	118.36 (15)	C15—C16—N2	110.37 (14)
C3—C2—H2A	120.8	C15—C16—H16	124.8
C1—C2—H2A	120.8	N2—C16—H16	124.8
C2—C3—C4	120.91 (16)	C15—C17—C7	112.29 (10)
C2—C3—H3A	119.5	C15—C17—C24	111.10 (10)
C4—C3—H3A	119.5	C7—C17—C24	113.71 (11)
C5—C4—C3	121.24 (16)	C15—C17—C18	110.79 (11)
C5—C4—H4	119.4	C7—C17—C18	107.14 (10)
C3—C4—H4	119.4	C24—C17—C18	101.17 (10)
C4—C5—C6	119.40 (14)	O1—C18—N3	125.60 (13)
C4—C5—H5	120.3	O1—C18—C17	126.71 (13)
C6—C5—H5	120.3	N3—C18—C17	107.69 (11)
C5—C6—C1	118.08 (13)	C20—C19—C24	122.21 (13)
C5—C6—C7	136.10 (12)	C20—C19—N3	128.64 (13)
C1—C6—C7	105.80 (12)	C24—C19—N3	109.14 (12)
C8—C7—C6	106.63 (12)	C19—C20—C21	117.26 (13)
C8—C7—C17	123.37 (12)	C19—C20—H20	121.4
C6—C7—C17	129.90 (11)	C21—C20—H20	121.4
C7—C8—N1	110.59 (13)	C22—C21—C20	121.41 (13)
C7—C8—H8	124.7	C22—C21—H21	119.3
N1—C8—H8	124.7	C20—C21—H21	119.3
N2—C9—C10	130.82 (15)	C21—C22—C23	120.55 (14)
N2—C9—C14	107.32 (14)	C21—C22—H22	119.7
C10—C9—C14	121.86 (15)	C23—C22—H22	119.7
C11—C10—C9	118.11 (15)	C24—C23—C22	118.65 (13)
C11—C10—H10	120.9	C24—C23—H23	120.7
C9—C10—H10	120.9	C22—C23—H23	120.7
C10—C11—C12	121.24 (16)	C23—C24—C19	119.91 (12)
C10—C11—H11	119.4	C23—C24—C17	130.86 (12)
C12—C11—H11	119.4	C19—C24—C17	109.21 (11)

C8—N1—C1—C2	−179.99 (16)	C16—C15—C17—C7	−137.91 (14)
C8—N1—C1—C6	0.08 (16)	C14—C15—C17—C7	48.44 (17)
N1—C1—C2—C3	179.55 (16)	C16—C15—C17—C24	93.5 (2)
C6—C1—C2—C3	−0.5 (3)	C14—C15—C17—C24	−80.16 (15)
C1—C2—C3—C4	−0.8 (3)	C16—C15—C17—C18	−18.15 (19)
C2—C3—C4—C5	1.0 (3)	C14—C15—C17—C18	168.21 (12)
C3—C4—C5—C6	0.2 (2)	C8—C7—C17—C15	37.08 (17)
C4—C5—C6—C1	−1.48 (19)	C6—C7—C17—C15	−147.15 (13)
C4—C5—C6—C7	−179.76 (14)	C8—C7—C17—C24	164.3 (1)
N1—C1—C6—C5	−178.37 (12)	C6—C7—C17—C24	−19.93 (18)
C2—C1—C6—C5	1.7 (2)	C8—C7—C17—C18	−84.79 (15)
N1—C1—C6—C7	0.39 (15)	C6—C7—C17—C18	90.98 (15)
C2—C1—C6—C7	−179.55 (14)	C19—N3—C18—O1	178.41 (14)
C5—C6—C7—C8	177.71 (14)	C19—N3—C18—C17	−2.54 (16)
C1—C6—C7—C8	−0.71 (14)	C15—C17—C18—O1	−60.28 (18)
C5—C6—C7—C17	1.4 (2)	C7—C17—C18—O1	62.52 (19)
C1—C6—C7—C17	−177.02 (12)	C24—C17—C18—O1	−178.16 (15)
C6—C7—C8—N1	0.79 (16)	C15—C17—C18—N3	120.68 (12)
C17—C7—C8—N1	177.40 (12)	C7—C17—C18—N3	−116.51 (12)
C1—N1—C8—C7	−0.55 (17)	C24—C17—C18—N3	2.81 (14)
C16—N2—C9—C10	−179.75 (18)	C18—N3—C19—C20	−177.52 (15)
C16—N2—C9—C14	−0.05 (19)	C18—N3—C19—C24	1.10 (17)
N2—C9—C10—C11	−179.91 (18)	C24—C19—C20—C21	−1.3 (2)
C14—C9—C10—C11	0.4 (3)	N3—C19—C20—C21	177.16 (15)
C9—C10—C11—C12	−0.7 (3)	C19—C20—C21—C22	0.6 (2)
C10—C11—C12—C13	0.5 (3)	C20—C21—C22—C23	0.1 (3)
C11—C12—C13—C14	−0.1 (2)	C21—C22—C23—C24	−0.2 (2)
C12—C13—C14—C9	−0.1 (2)	C22—C23—C24—C19	−0.4 (2)
C12—C13—C14—C15	−179.42 (15)	C22—C23—C24—C17	−178.43 (14)
N2—C9—C14—C13	−179.78 (13)	C20—C19—C24—C23	1.2 (2)
C10—C9—C14—C13	0.0 (2)	N3—C19—C24—C23	−177.49 (12)
N2—C9—C14—C15	−0.29 (16)	C20—C19—C24—C17	179.62 (13)
C10—C9—C14—C15	179.44 (15)	N3—C19—C24—C17	0.90 (15)
C13—C14—C15—C16	179.88 (15)	C15—C17—C24—C23	58.30 (18)
C9—C14—C15—C16	0.52 (15)	C7—C17—C24—C23	−69.54 (18)
C13—C14—C15—C17	−5.4 (2)	C18—C17—C24—C23	175.95 (14)
C9—C14—C15—C17	175.26 (12)	C15—C17—C24—C19	−119.85 (12)
C14—C15—C16—N2	−0.56 (17)	C7—C17—C24—C19	112.30 (12)
C17—C15—C16—N2	−175.23 (13)	C18—C17—C24—C19	−2.20 (14)
C9—N2—C16—C15	0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.913 (2)	162

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₇N₃O
M_r	363.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.0578 (12), 10.2342 (5), 18.1597 (9)
β (°)	125.861 (1)
V (Å³)	3623.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20359, 4278, 3677
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.134, 1.05
No. of reflections	4278
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top

O1—C18	1.217 (2)	C15—C17	1.511 (2)
C7—C17	1.516 (2)

C16—C15—C17—C24	93.5 (2)	C8—C7—C17—C24	164.3 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.913 (2)	162

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

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