Pelanserin: 3-[3-(4-phenyl­piperazin-1-yl)prop­yl]quinazoline-2,4(1H,3H)-dione

Aguirre Hernández, G.; Somanathan, R.; Bernès, S.

doi:10.1107/S160053681401602X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o878

doi:10.1107/S160053681401602X

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Pelanserin: 3-[3-(4-phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione

Gerardo Aguirre Hernández,^a ^* Ratnasamy Somanathan ^a and Sylvain Bernès ^b ‡

^aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500 Tijuana, B.C., Mexico, and ^bDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, N.L., Mexico
^*Correspondence e-mail: gaguirre777@gmail.com

Edited by G. Smith, Queensland University of Technology, Australia (Received 11 June 2014; accepted 9 July 2014; online 23 July 2014)

The title compound, C₂₁H₂₄N₄O₂, is a potent serotonin 5-HT₂ and α₁-adrenoceptor antagonist. The n-propyl chain links the quinazolinedione heterocycle and the phenylpiperazine group in which the benzene ring is equatorially located and the piperazine ring has the expected chair conformation. The dihedral angle between the planes of the benzene ring and the quinazolinedione ring system is 74.1 (1)°. In the crystal, molecules form centrosymmetric dimers through R₂²(8) hydrogen-bonded rings involving the amine and one carbonyl group of the quinazolinedione moiety. These dimers are extended into chains extending along the a-axis direction through expanded centrosymmetric cyclic C—H⋯O associations involving the second carbonyl group, giving R₂²(20) and R₁²(7) motifs.

Keywords: crystal structure.

CCDC reference: 1013055

Related literature

For the synthesis of pelanserin, see: Cortez et al. (1991 ); Garcia et al. (2000 ); Li et al. (2011 ). For the pharmacology of pelanserin, see: Flores-Murrieta et al. (1990 , 1992 ); Villalobos-Molina et al. (1995 ). For the structure of quinazoline-2,4(1H,3H)-dione, see: Liu (2008 ).

Experimental

Crystal data

C₂₁H₂₄N₄O₂
M_r = 364.44
Monoclinic, P 2₁ /c
a = 15.7531 (17) Å
b = 5.4345 (10) Å
c = 22.756 (3) Å
β = 104.506 (9)°
V = 1886.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.60 × 0.30 × 0.10 mm

Data collection

Bruker P4 diffractometer
3452 measured reflections
3323 independent reflections
1301 reflections with I > 2σ(I)
R_int = 0.077
3 standard reflections every 97 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.148
S = 0.99
3323 reflections
247 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2ⁱ	0.95 (4)	1.85 (4)	2.799 (5)	171 (4)
C18—H18A⋯O10ⁱⁱ	0.97	2.71	3.625 (6)	157
C25—H25A⋯O10ⁱⁱ	0.93	2.59	3.404 (6)	147
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL2013.

Supporting information

CCDC reference: 1013055

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681401602X/zs2304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401602X/zs2304Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681401602X/zs2304Isup3.cml

checkCIF report

Comment top

Quinazolinediones are important heterocycles, which have been shown to possess pharmacologically interesting properties, displaying for example anti-hypertensive, or antidiabetic activity. Among these, synthetic pelanserin (TR-2515) is a well-established potent antihypertensive agent, a feature attributed to its 5-HT₂ and α₁-adrenoceptor antagonist activity (Flores-Murrieta et al., 1990, 1992; Villalobos-Molina et al., 1995). Indeed, this molecule presents an activity comparable to that of ketanserin, a clinically used drug. Both molecules also share the quinazoline-2,4-dione scaffold.

We synthesized pelanserin via a ring closure procedure we have developed, based on the reaction between an o-aminobenzamide and triphosgene (Cortez et al., 1991; Garcia et al., 2000). Such a strategy has also been used starting from isatoic anhydride and a readily available primary amine, with triphosgene as ring closure agent (Li et al., 2011).

The title compound has the expected conformation, with the extended n-propyl chain linking the heterocyclic systems (Fig. 1). The quinazolinedione group has the same geometry as that observed for free quinazoline-2,4(1H,3H)-dione (Liu, 2008), and the piperazine ring is found in the chair conformation, with the phenyl substituent group equatorially located. Both lone pairs in the piperazine ring are thus placed in axial positions. The dihedral angle between phenyl and quinazolinedione rings is 74.1 (1)°, giving a twisted conformation for the overall molecule. The crystal structure is dominated by common intermolecular R₂²(8) hydrogen-bonded ring motifs formed through N3—H···O2ⁱ hydrogen bonds (Table 2). These centrosymmetric dimers are extended through weak C—H···O hydrogen-bonding associations involving the second carbonyl group in a bifurcated R₁²(7) motif (C18—H···O10ⁱⁱ, C25—H···O10ⁱⁱ), giving an expanded cyclic R₂²(20) motif in one-dimensional chains extending along a (Fig. 2).

Related literature top

For the synthesis of pelanserin, see: Cortez et al. (1991); Garcia et al. (2000); Li et al. (2011). For the pharmacology of pelanserin, see: Flores-Murrieta et al. (1990, 1992); Villalobos-Molina et al. (1995). For the structure of quinazoline-2,4(1H,3H)-dione, see: Liu (2008).

Experimental top

2-Amino-N-[3-(4-phenhylpiperazin-1-yl)propyl]benzamide (1.7 g, 5 mmol) was stirred in CH₂Cl₂ (50 ml) at room temperature and triphosgene (0.5 g, 1.7 mmol) in CH₂Cl₂ (10 ml) was added. The mixture was refluxed for 2 h. The organic phase was washed with water and dried over MgSO₄. The solvent was removed under reduced pressure, to give a solid product, which was recrystallized from ethanol, affording pure pelanserin. M.p. 190–192 °C, yield 88%; IR (KBr): 3358 (NH), 2982 (CH), 1737 cm^-1 (C═O). ¹H-NMR (200 MHz, CDCl₃, p.p.m.): δ 10.70 (s, 1H), 8.12 (d, 1H, J = 8.0 Hz), 7.0 (t, 1H, J = 8.4 Hz), 7.25 (m, 4H), 6.87 (m, 3H), 4.19 (t, 2H, J = 6.9 Hz), 3.12 (t, 4H, J = 6.0 Hz), 2.61 (m, 6H), 1.95 (q, 2H); ¹³C-NMR (50 MHz, CDCl₃, p.p.m.): δ 162, 152, 151, 139, 135, 129, 128, 123, 119, 116, 114, 56, 53, 49, 30, 25. EIMS (m/z): 364 [M⁺, 3], 175 [100]. Anal. calcd. for C₂₁H₂₄N₄O₂: C 69.21, H 6.64%; found: C 69.23, H 6.58%.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, with 30% probability level displacement ellipsoids for non-H atoms.
	Fig. 2. Part of the crystal structure, showing hydrogen bonds as dashed lines.

3-[3-(4-Phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione top

Crystal data top

C₂₁H₂₄N₄O₂	D_x = 1.283 Mg m⁻³
M_r = 364.44	Melting point = 463–465 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.7531 (17) Å	Cell parameters from 33 reflections
b = 5.4345 (10) Å	θ = 4.7–10.7°
c = 22.756 (3) Å	µ = 0.09 mm⁻¹
β = 104.506 (9)°	T = 296 K
V = 1886.0 (5) Å³	Plate, yellow
Z = 4	0.60 × 0.30 × 0.10 mm
F(000) = 776

Data collection top

Bruker P4 diffractometer	R_int = 0.077
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.5°
Graphite monochromator	h = 0→18
2θ/ω scans	k = 0→6
3452 measured reflections	l = −27→26
3323 independent reflections	3 standard reflections every 97 reflections
1301 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.072	Hydrogen site location: mixed
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0399P)²] where P = (F_o² + 2F_c²)/3
3323 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³
0 constraints

Crystal data top

C₂₁H₂₄N₄O₂	V = 1886.0 (5) Å³
M_r = 364.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.7531 (17) Å	µ = 0.09 mm⁻¹
b = 5.4345 (10) Å	T = 296 K
c = 22.756 (3) Å	0.60 × 0.30 × 0.10 mm
β = 104.506 (9)°

Data collection top

Bruker P4 diffractometer	R_int = 0.077
3452 measured reflections	3 standard reflections every 97 reflections
3323 independent reflections	intensity decay: 1%
1301 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.18 e Å⁻³
3323 reflections	Δρ_min = −0.19 e Å⁻³
247 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.8261 (2)	0.4446 (7)	0.56297 (15)	0.0441 (10)
C2	0.8955 (3)	0.4694 (10)	0.5359 (2)	0.0476 (13)
O2	0.90428 (19)	0.3299 (6)	0.49494 (13)	0.0615 (10)
N3	0.9524 (2)	0.6547 (8)	0.55692 (17)	0.0510 (11)
H3	1.004 (3)	0.669 (8)	0.5430 (17)	0.061*
C4	0.9477 (3)	0.8081 (9)	0.60436 (19)	0.0437 (12)
C5	1.0100 (3)	0.9929 (9)	0.6239 (2)	0.0530 (14)
H5A	1.0556	1.0136	0.6051	0.064*
C6	1.0035 (3)	1.1443 (10)	0.6712 (2)	0.0602 (14)
H6A	1.0447	1.2681	0.6842	0.072*
C7	0.9361 (3)	1.1131 (10)	0.6995 (2)	0.0592 (14)
H7A	0.9326	1.2143	0.7318	0.071*
C8	0.8741 (3)	0.9326 (9)	0.6800 (2)	0.0536 (14)
H8A	0.8282	0.9145	0.6986	0.064*
C9	0.8798 (3)	0.7762 (9)	0.63228 (18)	0.0416 (12)
C10	0.8130 (3)	0.5898 (9)	0.61014 (19)	0.0457 (12)
O10	0.7479 (2)	0.5615 (6)	0.62947 (13)	0.0649 (10)
C11	0.7659 (3)	0.2377 (9)	0.54229 (18)	0.0488 (13)
H11A	0.7447	0.1788	0.5763	0.059*
H11B	0.7982	0.1045	0.5296	0.059*
C12	0.6878 (3)	0.3001 (9)	0.49053 (18)	0.0506 (13)
H12A	0.7075	0.3740	0.4575	0.061*
H12B	0.6502	0.4169	0.5041	0.061*
C13	0.6375 (3)	0.0642 (9)	0.46908 (18)	0.0502 (13)
H13A	0.6737	−0.0416	0.4510	0.060*
H13B	0.6271	−0.0211	0.5041	0.060*
N14	0.5535 (2)	0.1028 (7)	0.42500 (15)	0.0435 (10)
C15	0.5664 (3)	0.1797 (9)	0.36668 (18)	0.0551 (14)
H15A	0.6014	0.0573	0.3524	0.066*
H15B	0.5985	0.3337	0.3717	0.066*
C16	0.4801 (3)	0.2128 (9)	0.31949 (19)	0.0605 (14)
H16A	0.4476	0.3471	0.3317	0.073*
H16B	0.4917	0.2565	0.2809	0.073*
N17	0.4269 (2)	−0.0093 (7)	0.31190 (15)	0.0432 (10)
C18	0.4153 (3)	−0.0908 (9)	0.37070 (18)	0.0528 (13)
H18A	0.3833	−0.2451	0.3657	0.063*
H18B	0.3811	0.0302	0.3862	0.063*
C19	0.5027 (3)	−0.1247 (9)	0.41534 (19)	0.0555 (14)
H19A	0.4935	−0.1805	0.4538	0.067*
H19B	0.5356	−0.2507	0.4004	0.067*
C20	0.3524 (3)	−0.0201 (9)	0.26258 (19)	0.0446 (12)
C21	0.3356 (3)	0.1559 (10)	0.2177 (2)	0.0651 (16)
H21A	0.3723	0.2919	0.2209	0.078*
C22	0.2645 (3)	0.1331 (11)	0.1677 (2)	0.0708 (17)
H22A	0.2545	0.2541	0.1378	0.085*
C23	0.2089 (3)	−0.0630 (11)	0.1614 (2)	0.0643 (15)
H23A	0.1614	−0.0777	0.1278	0.077*
C24	0.2254 (3)	−0.2380 (11)	0.2063 (2)	0.0656 (15)
H24A	0.1878	−0.3722	0.2031	0.079*
C25	0.2961 (3)	−0.2202 (10)	0.2562 (2)	0.0559 (14)
H25A	0.3061	−0.3428	0.2857	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.033 (2)	0.057 (3)	0.043 (2)	−0.005 (2)	0.0113 (18)	0.003 (2)
C2	0.032 (3)	0.069 (4)	0.038 (3)	0.001 (3)	0.000 (2)	0.000 (3)
O2	0.059 (2)	0.079 (3)	0.0492 (19)	−0.012 (2)	0.0193 (17)	−0.019 (2)
N3	0.037 (2)	0.065 (3)	0.052 (2)	−0.010 (2)	0.013 (2)	−0.008 (2)
C4	0.039 (3)	0.049 (3)	0.040 (3)	0.002 (3)	0.005 (2)	0.001 (3)
C5	0.040 (3)	0.063 (4)	0.053 (3)	0.001 (3)	0.005 (2)	0.012 (3)
C6	0.057 (3)	0.056 (4)	0.061 (3)	−0.002 (3)	0.002 (3)	−0.002 (3)
C7	0.065 (3)	0.056 (4)	0.054 (3)	0.006 (3)	0.010 (3)	−0.005 (3)
C8	0.047 (3)	0.063 (4)	0.050 (3)	0.014 (3)	0.011 (2)	0.007 (3)
C9	0.039 (3)	0.048 (3)	0.034 (2)	0.012 (3)	0.003 (2)	0.007 (2)
C10	0.042 (3)	0.051 (3)	0.042 (3)	0.006 (3)	0.007 (2)	0.004 (3)
O10	0.054 (2)	0.079 (3)	0.073 (2)	−0.009 (2)	0.0345 (18)	−0.008 (2)
C11	0.036 (3)	0.061 (3)	0.049 (3)	−0.001 (3)	0.010 (2)	0.004 (3)
C12	0.044 (3)	0.052 (3)	0.048 (3)	−0.005 (3)	−0.002 (2)	0.002 (3)
C13	0.048 (3)	0.051 (3)	0.048 (3)	−0.001 (3)	0.005 (2)	−0.003 (3)
N14	0.044 (2)	0.046 (3)	0.039 (2)	−0.006 (2)	0.0074 (18)	−0.005 (2)
C15	0.051 (3)	0.064 (4)	0.048 (3)	−0.015 (3)	0.008 (2)	0.000 (3)
C16	0.059 (3)	0.064 (4)	0.055 (3)	−0.016 (3)	0.007 (3)	0.006 (3)
N17	0.045 (2)	0.048 (3)	0.038 (2)	−0.010 (2)	0.0131 (18)	0.000 (2)
C18	0.047 (3)	0.062 (4)	0.048 (3)	−0.018 (3)	0.008 (2)	−0.001 (3)
C19	0.060 (3)	0.060 (4)	0.045 (3)	−0.011 (3)	0.012 (2)	0.000 (3)
C20	0.044 (3)	0.050 (3)	0.039 (3)	0.002 (3)	0.008 (2)	−0.010 (3)
C21	0.077 (4)	0.067 (4)	0.044 (3)	−0.011 (3)	0.000 (3)	−0.002 (3)
C22	0.076 (4)	0.076 (4)	0.051 (3)	0.001 (4)	0.000 (3)	0.008 (3)
C23	0.049 (3)	0.087 (4)	0.054 (3)	0.000 (4)	0.007 (3)	−0.011 (3)
C24	0.053 (3)	0.079 (4)	0.064 (3)	−0.022 (3)	0.015 (3)	−0.016 (4)
C25	0.049 (3)	0.058 (4)	0.056 (3)	−0.005 (3)	0.004 (3)	−0.006 (3)

Geometric parameters (Å, º) top

N1—C2	1.389 (5)	C13—H13B	0.9700
N1—C10	1.389 (5)	N14—C15	1.453 (5)
N1—C11	1.470 (5)	N14—C19	1.459 (5)
C2—O2	1.235 (5)	C15—C16	1.518 (5)
C2—N3	1.353 (5)	C15—H15A	0.9700
N3—C4	1.381 (5)	C15—H15B	0.9700
N3—H3	0.95 (4)	C16—N17	1.454 (5)
C4—C9	1.385 (5)	C16—H16A	0.9700
C4—C5	1.397 (6)	C16—H16B	0.9700
C5—C6	1.379 (6)	N17—C20	1.407 (5)
C5—H5A	0.9300	N17—C18	1.464 (5)
C6—C7	1.384 (6)	C18—C19	1.504 (5)
C6—H6A	0.9300	C18—H18A	0.9700
C7—C8	1.377 (6)	C18—H18B	0.9700
C7—H7A	0.9300	C19—H19A	0.9700
C8—C9	1.400 (6)	C19—H19B	0.9700
C8—H8A	0.9300	C20—C21	1.375 (6)
C9—C10	1.456 (6)	C20—C25	1.388 (6)
C10—O10	1.223 (5)	C21—C22	1.388 (6)
C11—C12	1.513 (5)	C21—H21A	0.9300
C11—H11A	0.9700	C22—C23	1.364 (6)
C11—H11B	0.9700	C22—H22A	0.9300
C12—C13	1.522 (6)	C23—C24	1.373 (6)
C12—H12A	0.9700	C23—H23A	0.9300
C12—H12B	0.9700	C24—C25	1.381 (5)
C13—N14	1.462 (5)	C24—H24A	0.9300
C13—H13A	0.9700	C25—H25A	0.9300

C2—N1—C10	125.0 (4)	C15—N14—C19	107.6 (3)
C2—N1—C11	116.7 (4)	C15—N14—C13	111.0 (3)
C10—N1—C11	118.2 (4)	C19—N14—C13	110.5 (4)
O2—C2—N3	122.3 (4)	N14—C15—C16	112.0 (4)
O2—C2—N1	121.6 (5)	N14—C15—H15A	109.2
N3—C2—N1	116.1 (5)	C16—C15—H15A	109.2
C2—N3—C4	124.4 (4)	N14—C15—H15B	109.2
C2—N3—H3	119 (3)	C16—C15—H15B	109.2
C4—N3—H3	115 (3)	H15A—C15—H15B	107.9
N3—C4—C9	118.8 (5)	N17—C16—C15	111.9 (4)
N3—C4—C5	120.7 (5)	N17—C16—H16A	109.2
C9—C4—C5	120.4 (5)	C15—C16—H16A	109.2
C6—C5—C4	119.6 (5)	N17—C16—H16B	109.2
C6—C5—H5A	120.2	C15—C16—H16B	109.2
C4—C5—H5A	120.2	H16A—C16—H16B	107.9
C5—C6—C7	120.4 (5)	C20—N17—C16	118.0 (4)
C5—C6—H6A	119.8	C20—N17—C18	116.5 (3)
C7—C6—H6A	119.8	C16—N17—C18	110.1 (3)
C8—C7—C6	120.1 (5)	N17—C18—C19	110.6 (3)
C8—C7—H7A	119.9	N17—C18—H18A	109.5
C6—C7—H7A	119.9	C19—C18—H18A	109.5
C7—C8—C9	120.3 (5)	N17—C18—H18B	109.5
C7—C8—H8A	119.8	C19—C18—H18B	109.5
C9—C8—H8A	119.8	H18A—C18—H18B	108.1
C4—C9—C8	119.1 (5)	N14—C19—C18	111.9 (4)
C4—C9—C10	120.1 (4)	N14—C19—H19A	109.2
C8—C9—C10	120.6 (5)	C18—C19—H19A	109.2
O10—C10—N1	120.5 (5)	N14—C19—H19B	109.2
O10—C10—C9	124.1 (5)	C18—C19—H19B	109.2
N1—C10—C9	115.4 (4)	H19A—C19—H19B	107.9
N1—C11—C12	114.3 (4)	C21—C20—C25	117.9 (4)
N1—C11—H11A	108.7	C21—C20—N17	122.0 (5)
C12—C11—H11A	108.7	C25—C20—N17	119.9 (4)
N1—C11—H11B	108.7	C20—C21—C22	120.8 (5)
C12—C11—H11B	108.7	C20—C21—H21A	119.6
H11A—C11—H11B	107.6	C22—C21—H21A	119.6
C11—C12—C13	108.5 (4)	C23—C22—C21	121.4 (5)
C11—C12—H12A	110.0	C23—C22—H22A	119.3
C13—C12—H12A	110.0	C21—C22—H22A	119.3
C11—C12—H12B	110.0	C22—C23—C24	117.8 (5)
C13—C12—H12B	110.0	C22—C23—H23A	121.1
H12A—C12—H12B	108.4	C24—C23—H23A	121.1
N14—C13—C12	114.1 (4)	C23—C24—C25	121.8 (5)
N14—C13—H13A	108.7	C23—C24—H24A	119.1
C12—C13—H13A	108.7	C25—C24—H24A	119.1
N14—C13—H13B	108.7	C24—C25—C20	120.2 (5)
C12—C13—H13B	108.7	C24—C25—H25A	119.9
H13A—C13—H13B	107.6	C20—C25—H25A	119.9

C10—N1—C2—O2	178.3 (4)	C10—N1—C11—C12	92.2 (4)
C11—N1—C2—O2	2.5 (6)	N1—C11—C12—C13	173.4 (4)
C10—N1—C2—N3	−1.7 (6)	C11—C12—C13—N14	171.7 (3)
C11—N1—C2—N3	−177.5 (4)	C12—C13—N14—C15	71.1 (5)
O2—C2—N3—C4	−176.9 (4)	C12—C13—N14—C19	−169.6 (4)
N1—C2—N3—C4	3.1 (6)	C19—N14—C15—C16	57.1 (5)
C2—N3—C4—C9	−1.2 (6)	C13—N14—C15—C16	178.1 (4)
C2—N3—C4—C5	179.0 (4)	N14—C15—C16—N17	−56.3 (5)
N3—C4—C5—C6	179.7 (4)	C15—C16—N17—C20	−169.2 (4)
C9—C4—C5—C6	−0.1 (6)	C15—C16—N17—C18	53.8 (5)
C4—C5—C6—C7	0.4 (7)	C20—N17—C18—C19	167.0 (4)
C5—C6—C7—C8	−1.0 (7)	C16—N17—C18—C19	−55.2 (5)
C6—C7—C8—C9	1.3 (7)	C15—N14—C19—C18	−59.3 (5)
N3—C4—C9—C8	−179.4 (4)	C13—N14—C19—C18	179.4 (3)
C5—C4—C9—C8	0.5 (6)	N17—C18—C19—N14	59.6 (5)
N3—C4—C9—C10	−2.3 (6)	C16—N17—C20—C21	8.9 (6)
C5—C4—C9—C10	177.5 (4)	C18—N17—C20—C21	143.2 (4)
C7—C8—C9—C4	−1.1 (6)	C16—N17—C20—C25	−175.1 (4)
C7—C8—C9—C10	−178.1 (4)	C18—N17—C20—C25	−40.7 (6)
C2—N1—C10—O10	176.8 (4)	C25—C20—C21—C22	−0.1 (7)
C11—N1—C10—O10	−7.4 (6)	N17—C20—C21—C22	176.1 (4)
C2—N1—C10—C9	−1.5 (6)	C20—C21—C22—C23	0.3 (8)
C11—N1—C10—C9	174.3 (3)	C21—C22—C23—C24	0.1 (8)
C4—C9—C10—O10	−174.7 (4)	C22—C23—C24—C25	−0.7 (8)
C8—C9—C10—O10	2.3 (7)	C23—C24—C25—C20	0.9 (7)
C4—C9—C10—N1	3.5 (6)	C21—C20—C25—C24	−0.5 (7)
C8—C9—C10—N1	−179.5 (4)	N17—C20—C25—C24	−176.7 (4)
C2—N1—C11—C12	−91.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.95 (4)	1.85 (4)	2.799 (5)	171 (4)
C18—H18A···O10ⁱⁱ	0.97	2.71	3.625 (6)	157
C25—H25A···O10ⁱⁱ	0.93	2.59	3.404 (6)	147

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.95 (4)	1.85 (4)	2.799 (5)	171 (4)
C18—H18A···O10ⁱⁱ	0.97	2.71	3.625 (6)	157
C25—H25A···O10ⁱⁱ	0.93	2.59	3.404 (6)	147

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

Footnotes

‡Currently unaffiliated to UANL.

References

Cortez, R., Rivero, I. A., Somanathan, R., Aguirre, G., Ramirez, F. & Hong, E. (1991). Synth. Commun. 21, 285–292. CrossRef CAS Web of Science Google Scholar
Flores-Murrieta, F. J., Castañeda Hernández, G. & Hong, E. (1990). Arch. Inst. Cardiol. Mex. 60, 347–351. CAS PubMed Google Scholar
Flores-Murrieta, F. J., Herrera, J. E., Castañeda-Hernández, G. & Hong, E. (1992). Proc. West. Pharmacol. Soc. 35, 113–116. PubMed CAS Google Scholar
Garcia, J. D., Somanathan, R., Rivero, I. A., Aguirre, G. & Hellberg, L. H. (2000). Synth. Commun. 30, 2707–2711. Web of Science CrossRef CAS Google Scholar
Li, X., Lee, Y. R. & Kim, S. H. (2011). Bull. Korean Chem. Soc. 32, 3480–3482. Web of Science CrossRef CAS Google Scholar
Liu, G. (2008). Acta Cryst. E64, o1677. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Villalobos-Molina, R., Ibarra, M. & Hong, E. (1995). Eur. J. Pharmacol. 277, 181–185. CAS PubMed Web of Science Google Scholar