2-Ethyl-6-(2-pyrid­yl)-5,6,6a,11b-tetra­hydro-7H-indeno[2,1-c]quinoline

Bohórquez, A.R.R.; Kouznetsov, V.V.; González, T.; Briceño, A.

doi:10.1107/S1600536810005805

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o680-o681

doi:10.1107/S1600536810005805

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2-Ethyl-6-(2-pyridyl)-5,6,6a,11b-tetrahydro-7H-indeno[2,1-c]quinoline

Arnold R. Romero Bohórquez,^a Vladimir V. Kouznetsov,^a Teresa González ^b and Alexander Briceño ^b ^*

^aLaboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, Apartado 678, Bucaramanga, Colombia, and ^bCentro de Química, Instituto Venezolano de Investigaciones Científicas (IVIC), Apartado 21827, Caracas 1020-A, Venezuela
^*Correspondence e-mail: abriceno@ivic.ve

(Received 12 January 2010; accepted 11 February 2010; online 20 February 2010)

The title compound, C₂₃H₂₂N₂, was obtained using the three-component imino Diels–Alder reaction via a one-pot condensation between anilines, α-pyridinecarboxyaldehyde and indene using BF₃·OEt₂ as the catalyst. The molecular structure reveals the cis-form as the unique diastereoisomer. The crystal structure comprises one-dimensional zigzag ribbons connected via N—H⋯N hydrogen bonds. C—H⋯π interactions also occur.

Related literature

For background to polycyclic quinoline derivatives, see: Denny & Baguley (2003 ); Gelderblom & Sparreboom (2006 ). For the biological activity of quinolines, see: Ewesuedo et al. (2001 ); Ishida & Asao (2002 ); Kouznetsov et al. (2006 ); Li et al. (2006 ); Ohyama et al. (1999 ); Priel et al. (1991 ); Twelves et al. (1999 ); Martínez & Chacón-García (2005 ); Pommier (2006 ).

Experimental

Crystal data

C₂₃H₂₂N₂
M_r = 326.43
Monoclinic, P 2₁ /c
a = 13.241 (4) Å
b = 15.801 (4) Å
c = 8.789 (2) Å
β = 101.168 (6)°
V = 1804.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.26 mm

Data collection

Rigaku AFC7S Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.971, T_max = 0.981
20284 measured reflections
3688 independent reflections
2420 reflections with I > 2σ(I)
R_int = 0.044
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.157
S = 1.07
3688 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.87	2.53	3.345 (2)	157
C20—H20⋯N1	0.93	2.51	2.825 (3)	100
C14—H14⋯Cg4ⁱⁱ	0.93	2.74	3.611 (2)	153
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1.

Data collection: CrystalClear (Rigaku, 2002 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810005805/tk2615sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005805/tk2615Isup2.hkl

checkCIF report

Comment top

Within the quinoline family, polycyclic analogues are the most relevant compounds due to their broad potential as antitumoral agents (Gelderblom & Sparreboom, 2006; Denny & Baguley, 2003). Since the discovery of camptothecin, a natural topopisomerase (topo) I inhibitor (Pommier, 2006; Priel et al., 1991), a constant search for new compounds with the ability for inhibit the topoisomerases I/II enzymes has been undertaken (Li et al., 2006; Martínez & Chacón-García, 2005). The compound (6-[2-(dimethylamino)ethylamino]-3-hydroxy-7H-indeno[2,1-c] quinolin-7-one dihydrochloride (known as TAS-103) presents potent cytotoxicity in different leukemia lines (Twelves et al., 1999; Ohyama et al., 1999). The exhibited anti-cancer activity is due to its ability to function as a dual inhibitor of both topo I/II, and it has been investigated in clinical studies in recent years (Ewesuedo et al., 2001; Ishida & Asao, 2002).

In our preliminary studies of TAS-103 analogues, we have developed the synthesis (using the imino Diels Alder reaction) and studied the biological activity of the 6-α-pyridinyl- tetrahydro)indeno[2,1-c]quinolines (Kouznetsov et al., 2006). It was found that these compounds were active against MCF-7, H-460 and SF-268 cancer cell lines making them potential anti-cancer agents (Kouznetsov et al., 2006).

In order to obtain detailed information on its molecular conformation and the stereochemistry of the reaction, in this contribution, the molecular structure of the title compound, (I), is described. The structural analysis indicated (I) exists in the cis-form as a unique regio- and diastereo-isomer (Fig. 1). The tetrahydropyridine ring adopts a half-chair conformation and the indene ring displays an envelope configuration. The crystal packing of (I) consists of one-dimensional zigzag ribbons that run along the c direction and linked via N—H···N hydrogen bonding interactions (Fig. 2 & Table 1).

Related literature top

For background to polycyclic quinoline derivatives, see: Denny & Baguley (2003); Gelderblom & Sparreboom (2006). For the biological activity of quinolines, see: Ewesuedo et al. (2001); Ishida & Asao (2002); Kouznetsov et al. (2006); Li et al. (2006); Ohyama et al. (1999); Priel et al. (1991); Twelves et al. (1999); Martínez & Chacón-García (2005); Pommier (2006).

Experimental top

A mixture of aryl amine (3.6 mmol) and α-pyridinecarboxyaldehyde (4.0 mmol) in anhydrous CH₃CN (15 ml) was stirred at room temperature for 30 min after which BF₃.OEt₂ (3.6 mmol) was added. Over a period of 20 min, an acetonitrile solution (10 ml) of indene (4.0 mmol) was added dropwise. The resulting mixture was stirred at 343 K for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (3 x 15 ml). The organic layer was separated and dried (Na₂SO₄), concentrated in vacuo, and the resulting product was purified by column chromatography (silica gel, petroleum ether: EtOAc) to afford pure (I) as a colorless solid, mp 424–425 K (yield 43%). This compound was recrystallized by slow evaporation from the solvent mixture, hexane-ethyl acetate.

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. View of a one-dimensional ribbon aligned along the c axis, generated by N—H···N hydrogen bonds. Intermolecular hydrogen bonds are indicated by dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

2-Ethyl-6-(2-pyridyl)-5,6,6a,11b-tetrahydro-7H -indeno[2,1-c]quinoline top

Crystal data top

C₂₃H₂₂N₂	F(000) = 696
M_r = 326.43	D_x = 1.202 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11041 reflections
a = 13.241 (4) Å	θ = 1.6–27.7°
b = 15.801 (4) Å	µ = 0.07 mm⁻¹
c = 8.789 (2) Å	T = 293 K
β = 101.168 (6)°	Block, yellow
V = 1804.0 (8) Å³	0.30 × 0.28 × 0.26 mm
Z = 4

Data collection top

Rigaku AFC7S Mercury diffractometer	3688 independent reflections
Radiation source: Normal-focus sealed tube	2420 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 28.0°, θ_min = 2.0°
Absorption correction: multi-scan (Jacobson, 1998)	h = −15→15
T_min = 0.971, T_max = 0.981	k = −18→20
20284 measured reflections	l = −11→11

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0698P)² + 0.2578P] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₃H₂₂N₂	V = 1804.0 (8) Å³
M_r = 326.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.241 (4) Å	µ = 0.07 mm⁻¹
b = 15.801 (4) Å	T = 293 K
c = 8.789 (2) Å	0.30 × 0.28 × 0.26 mm
β = 101.168 (6)°

Data collection top

Rigaku AFC7S Mercury diffractometer	3688 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2420 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.981	R_int = 0.044
20284 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
3688 reflections	Δρ_min = −0.20 e Å⁻³
226 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
N1	0.02307 (11)	0.64024 (9)	0.43799 (17)	0.0490 (4)
H1N	−0.0192	0.6589	0.3565	0.059*
N2	−0.13358 (12)	0.73555 (10)	0.68890 (19)	0.0562 (4)
C1	0.00785 (13)	0.68474 (11)	0.5771 (2)	0.0460 (4)
H1	0.0242	0.7447	0.5668	0.055*
C2	0.07995 (13)	0.64878 (11)	0.7193 (2)	0.0458 (4)
H2	0.0741	0.6845	0.8084	0.055*
C3	0.05427 (14)	0.55713 (11)	0.7591 (2)	0.0528 (5)
H3A	0.0073	0.5563	0.8311	0.063*
H3B	0.0237	0.5261	0.6663	0.063*
C4	0.15662 (15)	0.52035 (11)	0.8317 (2)	0.0499 (5)
C5	0.17744 (17)	0.44613 (13)	0.9155 (2)	0.0636 (6)
H5	0.1240	0.4127	0.9366	0.076*
C6	0.2788 (2)	0.42241 (15)	0.9675 (3)	0.0744 (7)
H6	0.2934	0.3721	1.0223	0.089*
C7	0.35794 (19)	0.47219 (16)	0.9391 (3)	0.0766 (7)
H7	0.4257	0.4555	0.9753	0.092*
C8	0.33764 (16)	0.54720 (14)	0.8568 (2)	0.0653 (6)
H8	0.3915	0.5811	0.8387	0.078*
C9	0.23611 (14)	0.57118 (11)	0.8019 (2)	0.0485 (5)
C10	0.19475 (13)	0.64765 (11)	0.7040 (2)	0.0456 (4)
H10	0.2292	0.6992	0.7495	0.055*
C11	0.20897 (13)	0.63816 (10)	0.5372 (2)	0.0434 (4)
C12	0.30732 (15)	0.63126 (11)	0.5033 (2)	0.0523 (5)
H12	0.3636	0.6365	0.5845	0.063*
C13	0.32582 (15)	0.61707 (12)	0.3557 (2)	0.0540 (5)
C14	0.24015 (16)	0.60999 (12)	0.2362 (2)	0.0545 (5)
H14	0.2494	0.5997	0.1356	0.065*
C15	0.14227 (14)	0.61795 (11)	0.2647 (2)	0.0485 (5)
H15	0.0864	0.6128	0.1828	0.058*
C16	0.12446 (13)	0.63354 (10)	0.4138 (2)	0.0427 (4)
C17	0.43476 (17)	0.60998 (15)	0.3268 (3)	0.0731 (7)
H17A	0.4802	0.5943	0.4230	0.088*
H17B	0.4371	0.5649	0.2526	0.088*
C18	0.4737 (2)	0.6887 (2)	0.2677 (5)	0.1291 (13)
H18A	0.5427	0.6798	0.2520	0.194*
H18B	0.4734	0.7334	0.3416	0.194*
H18C	0.4303	0.7040	0.1710	0.194*
C19	−0.10323 (13)	0.67742 (11)	0.5962 (2)	0.0459 (4)
C20	−0.16803 (15)	0.61310 (12)	0.5276 (2)	0.0562 (5)
H20	−0.1446	0.5731	0.4650	0.067*
C21	−0.26739 (16)	0.60932 (13)	0.5534 (3)	0.0620 (6)
H21	−0.3120	0.5669	0.5082	0.074*
C22	−0.29921 (16)	0.66882 (15)	0.6463 (3)	0.0667 (6)
H22	−0.3660	0.6680	0.6650	0.080*
C23	−0.23034 (16)	0.73019 (14)	0.7117 (3)	0.0667 (6)
H23	−0.2525	0.7703	0.7755	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0429 (9)	0.0609 (9)	0.0431 (9)	0.0008 (7)	0.0077 (7)	−0.0047 (7)
N2	0.0480 (10)	0.0581 (10)	0.0636 (11)	0.0033 (7)	0.0136 (8)	−0.0097 (8)
C1	0.0445 (11)	0.0427 (9)	0.0513 (11)	−0.0007 (7)	0.0103 (8)	−0.0045 (8)
C2	0.0460 (11)	0.0466 (10)	0.0451 (10)	−0.0006 (7)	0.0091 (8)	−0.0094 (8)
C3	0.0511 (12)	0.0547 (11)	0.0533 (11)	−0.0027 (8)	0.0122 (9)	0.0011 (9)
C4	0.0565 (12)	0.0515 (11)	0.0408 (10)	0.0000 (8)	0.0067 (8)	−0.0038 (8)
C5	0.0707 (15)	0.0608 (13)	0.0563 (12)	−0.0049 (10)	0.0051 (11)	0.0056 (10)
C6	0.0868 (18)	0.0677 (14)	0.0625 (14)	0.0120 (13)	−0.0013 (13)	0.0099 (11)
C7	0.0646 (16)	0.0928 (17)	0.0676 (15)	0.0176 (13)	0.0005 (12)	0.0117 (13)
C8	0.0509 (13)	0.0838 (15)	0.0593 (13)	0.0032 (10)	0.0056 (10)	0.0078 (11)
C9	0.0475 (12)	0.0563 (11)	0.0402 (10)	0.0008 (8)	0.0050 (8)	−0.0065 (8)
C10	0.0439 (11)	0.0461 (10)	0.0461 (10)	−0.0033 (7)	0.0066 (8)	−0.0066 (8)
C11	0.0439 (11)	0.0418 (9)	0.0445 (10)	−0.0030 (7)	0.0086 (8)	−0.0019 (7)
C12	0.0436 (12)	0.0595 (12)	0.0526 (12)	−0.0034 (8)	0.0065 (9)	−0.0006 (9)
C13	0.0498 (12)	0.0606 (12)	0.0540 (12)	0.0000 (8)	0.0164 (10)	0.0008 (9)
C14	0.0591 (13)	0.0595 (12)	0.0478 (11)	−0.0007 (9)	0.0178 (10)	−0.0022 (9)
C15	0.0489 (12)	0.0524 (11)	0.0430 (10)	−0.0017 (8)	0.0060 (9)	−0.0009 (8)
C16	0.0423 (11)	0.0394 (9)	0.0471 (10)	−0.0024 (7)	0.0107 (8)	−0.0004 (7)
C17	0.0557 (14)	0.0962 (17)	0.0727 (15)	0.0020 (11)	0.0255 (12)	−0.0024 (13)
C18	0.085 (2)	0.129 (3)	0.188 (4)	−0.0048 (18)	0.064 (2)	0.038 (3)
C19	0.0462 (11)	0.0439 (10)	0.0474 (10)	0.0035 (8)	0.0083 (8)	−0.0001 (8)
C20	0.0514 (12)	0.0529 (11)	0.0651 (13)	−0.0019 (8)	0.0134 (10)	−0.0089 (9)
C21	0.0496 (13)	0.0631 (13)	0.0738 (15)	−0.0089 (9)	0.0129 (11)	−0.0028 (11)
C22	0.0467 (12)	0.0813 (15)	0.0751 (15)	−0.0015 (11)	0.0192 (11)	−0.0010 (12)
C23	0.0532 (14)	0.0742 (14)	0.0765 (15)	0.0050 (10)	0.0218 (11)	−0.0149 (11)

Geometric parameters (Å, º) top

N1—C16	1.403 (2)	C10—H10	0.9800
N1—C1	1.458 (2)	C11—C12	1.395 (3)
N1—H1N	0.8700	C11—C16	1.401 (2)
N2—C23	1.337 (2)	C12—C13	1.384 (3)
N2—C19	1.340 (2)	C12—H12	0.9300
C1—C19	1.517 (2)	C13—C14	1.393 (3)
C1—C2	1.528 (2)	C13—C17	1.516 (3)
C1—H1	0.9800	C14—C15	1.373 (3)
C2—C3	1.543 (2)	C14—H14	0.9300
C2—C10	1.552 (2)	C15—C16	1.397 (2)
C2—H2	0.9800	C15—H15	0.9300
C3—C4	1.499 (3)	C17—C18	1.479 (3)
C3—H3A	0.9700	C17—H17A	0.9700
C3—H3B	0.9700	C17—H17B	0.9700
C4—C5	1.384 (3)	C18—H18A	0.9600
C4—C9	1.389 (3)	C18—H18B	0.9600
C5—C6	1.383 (3)	C18—H18C	0.9600
C5—H5	0.9300	C19—C20	1.390 (3)
C6—C7	1.371 (3)	C20—C21	1.379 (3)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.387 (3)	C21—C22	1.364 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.390 (3)	C22—C23	1.378 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.522 (2)	C23—H23	0.9300
C10—C11	1.521 (2)

C16—N1—C1	117.08 (14)	C12—C11—C16	118.00 (17)
C16—N1—H1N	112.5	C12—C11—C10	120.53 (16)
C1—N1—H1N	110.8	C16—C11—C10	121.44 (16)
C23—N2—C19	117.16 (17)	C13—C12—C11	123.67 (18)
N1—C1—C19	110.52 (14)	C13—C12—H12	118.2
N1—C1—C2	109.93 (14)	C11—C12—H12	118.2
C19—C1—C2	110.28 (14)	C12—C13—C14	116.96 (18)
N1—C1—H1	108.7	C12—C13—C17	121.04 (18)
C19—C1—H1	108.7	C14—C13—C17	122.00 (18)
C2—C1—H1	108.7	C15—C14—C13	120.98 (18)
C1—C2—C3	113.82 (14)	C15—C14—H14	119.5
C1—C2—C10	113.60 (14)	C13—C14—H14	119.5
C3—C2—C10	105.75 (14)	C14—C15—C16	121.60 (17)
C1—C2—H2	107.8	C14—C15—H15	119.2
C3—C2—H2	107.8	C16—C15—H15	119.2
C10—C2—H2	107.8	C15—C16—C11	118.71 (17)
C4—C3—C2	103.86 (15)	C15—C16—N1	119.70 (16)
C4—C3—H3A	111.0	C11—C16—N1	121.53 (16)
C2—C3—H3A	111.0	C18—C17—C13	113.9 (2)
C4—C3—H3B	111.0	C18—C17—H17A	108.8
C2—C3—H3B	111.0	C13—C17—H17A	108.8
H3A—C3—H3B	109.0	C18—C17—H17B	108.8
C5—C4—C9	120.69 (18)	C13—C17—H17B	108.8
C5—C4—C3	128.74 (18)	H17A—C17—H17B	107.7
C9—C4—C3	110.56 (16)	C17—C18—H18A	109.5
C6—C5—C4	119.1 (2)	C17—C18—H18B	109.5
C6—C5—H5	120.5	H18A—C18—H18B	109.5
C4—C5—H5	120.5	C17—C18—H18C	109.5
C7—C6—C5	120.8 (2)	H18A—C18—H18C	109.5
C7—C6—H6	119.6	H18B—C18—H18C	109.5
C5—C6—H6	119.6	N2—C19—C20	122.16 (17)
C6—C7—C8	120.5 (2)	N2—C19—C1	115.24 (15)
C6—C7—H7	119.8	C20—C19—C1	122.56 (16)
C8—C7—H7	119.8	C21—C20—C19	119.26 (18)
C7—C8—C9	119.4 (2)	C21—C20—H20	120.4
C7—C8—H8	120.3	C19—C20—H20	120.4
C9—C8—H8	120.3	C22—C21—C20	118.92 (19)
C4—C9—C8	119.61 (19)	C22—C21—H21	120.5
C4—C9—C10	111.27 (16)	C20—C21—H21	120.5
C8—C9—C10	129.09 (18)	C21—C22—C23	118.6 (2)
C11—C10—C9	111.60 (14)	C21—C22—H22	120.7
C11—C10—C2	113.02 (14)	C23—C22—H22	120.7
C9—C10—C2	102.20 (14)	N2—C23—C22	123.90 (19)
C11—C10—H10	109.9	N2—C23—H23	118.1
C9—C10—H10	109.9	C22—C23—H23	118.1
C2—C10—H10	109.9

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.87	2.53	3.345 (2)	157
C20—H20···N1	0.93	2.51	2.825 (3)	100
C14—H14···Cg4ⁱⁱ	0.93	2.74	3.611 (2)	153

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₂
M_r	326.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.241 (4), 15.801 (4), 8.789 (2)
β (°)	101.168 (6)
V (Å³)	1804.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.28 × 0.26

Data collection
Diffractometer	Rigaku AFC7S Mercury diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.971, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	20284, 3688, 2420
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.157, 1.07
No. of reflections	3688
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

Computer programs: CrystalClear (Rigaku, 2002), SHELXTL-NT (Sheldrick, 2008), SHELXTL-NT (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.87	2.53	3.345 (2)	157
C20—H20···N1	0.93	2.51	2.825 (3)	100
C14—H14···Cg4ⁱⁱ	0.93	2.74	3.611 (2)	153

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y, z−1.

Acknowledgements

The authors are grateful for financial support from the Colombian Institute for Science and Research (COLCIENCIAS-CENIVAM, grant No. 432–2004) and FONACIT-MCT Venezuela (project: LAB-199700821). ARRB also thanks COLCIENCIAS for a fellowship.

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Volume 66| Part 3| March 2010| Pages o680-o681

doi:10.1107/S1600536810005805

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