Crystal structure of (E)-2-(4-meth­oxy­styr­yl)-2,3-di­hydro-1H-perimidine aceto­nitrile monosolvate

Manimekalai, A.; Vijayalakshmi, N.; Selvanayagam, S.

doi:10.1107/S1600536814017000

organic compounds

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Volume 70| Part 9| September 2014| Page o959

doi:10.1107/S1600536814017000

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Crystal structure of (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate

A. Manimekalai,^a ^* N. Vijayalakshmi ^a and S. Selvanayagam ^b

^aDepartment of Chemistry, Faculty of Science, Annamalai University, Annamalainagar 608 002, India, and ^bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India
^*Correspondence e-mail: profmeka1@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 22 July 2014; accepted 23 July 2014; online 1 August 2014)

The title compound, C₂₀H₁₈N₂O·CH₃CN, a perimidine derivative, crystallized as an acetonitrile monosolvate. The planes of the naphthalene ring system and the methoxyphenyl ring are oriented almost perpendicular to one another, with a dihedral angle of 87.61 (6)°. The conformation about the C=C bond is E. The hexahydropyrimidine ring has an envelope conformation, with the methine C atom as the flap. In the crystal, the molecules are linked by N—H⋯N hydrogen bonds involving the acetonitrile solvent molecule as acceptor, forming zigzag chains propagating along [100].

Keywords: crystal structure; perimidine derivative; bifurcated hydrogen bonding.

CCDC reference: 1015577

1. Related literature

For the diverse range of biological activities of perimidines, see: Bu et al. (2001 ); Ivica et al. (2008 ); Azeez & Salih (2014 ). For a related structure, see: Maloney et al. (2013 ).

2. Experimental

2.1. Crystal data

C₂₀H₁₈N₂O·C₂H₃N
M_r = 343.42
Triclinic, $[P \overline 1]$
a = 7.8128 (7) Å
b = 8.4641 (7) Å
c = 14.7427 (14) Å
α = 79.513 (7)°
β = 83.861 (7)°
γ = 77.076 (7)°
V = 932.11 (15) Å³
Z = 2
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 292 K
0.30 × 0.30 × 0.19 mm

2.2. Data collection

Oxford Diffraction Gemini/EOS CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.840, T_max = 0.890
5843 measured reflections
3569 independent reflections
2940 reflections with I > 2σ(I)
R_int = 0.023

2.3. Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.142
S = 1.03
3569 reflections
246 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.88 (2)	2.49 (2)	3.305 (3)	154.1 (15)
N2—H2⋯N3ⁱⁱ	0.84 (2)	2.44 (2)	3.234 (2)	156.8 (16)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

CCDC reference: 1015577

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814017000/su2762sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017000/su2762Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814017000/su2762Isup3.cml

checkCIF report

Synthesis and crystallization top

A mixture of 4-methoxy-trans-cinnamaldehyde (0.01 mol), 1,8-diaminonaphthalene (0.01 mol) and a pinch of MgSO₄.7H₂O was finely grinded in a mortor. The mixture was then kept under microwave irradiation (LG Grill, Intellowave 160-800 W, consumption 800 W, output power 320 W and frequency 2450 MHz) operating in a cyclic mode to prevent intense boiling of the sample as well as aggregation of 320 W at 12 min. A brown colour solid separated out which was repeatedly recrystallized using CH₂Cl₂:CH₃CN (1:5) to obtain brown crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Atoms H1 and H2 were located from a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93-0.96 Å with U_iso(H) = 1.5U_eq(C-methyl) and U_iso(H) = 1.2U_eq for other C atoms.

Related literature top

For the diverse range of biological activities of perimidines, see: Bu et al. (2001); Ivica et al. (2008); Azeez & Salih (2014). For a related structure, see: Maloney et al. (2013).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2008); cell refinement: CrysAlis PRO (Oxford Diffraction, 2008); data reduction: CrysAlis PRO (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound, viewed along the b axis, showing the hydrogen bonds as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

(E)-2-(4-Methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate top

Crystal data top

C₂₀H₁₈N₂O·C₂H₃N	Z = 2
M_r = 343.42	F(000) = 364
Triclinic, P1	D_x = 1.224 Mg m⁻³
a = 7.8128 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.4641 (7) Å	Cell parameters from 2420 reflections
c = 14.7427 (14) Å	θ = 3.8–26.7°
α = 79.513 (7)°	µ = 0.60 mm⁻¹
β = 83.861 (7)°	T = 292 K
γ = 77.076 (7)°	Block, colourless
V = 932.11 (15) Å³	0.30 × 0.30 × 0.19 mm

Data collection top

Oxford Diffraction Gemini/EOS CCD diffractometer	2940 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
ϕ and ω scans	θ_max = 72.0°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008)	h = −8→9
T_min = 0.840, T_max = 0.890	k = −9→10
5843 measured reflections	l = −18→18
3569 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0768P)² + 0.0999P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3569 reflections	Δρ_max = 0.19 e Å⁻³
246 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (2)

Crystal data top

C₂₀H₁₈N₂O·C₂H₃N	γ = 77.076 (7)°
M_r = 343.42	V = 932.11 (15) Å³
Triclinic, P1	Z = 2
a = 7.8128 (7) Å	Cu Kα radiation
b = 8.4641 (7) Å	µ = 0.60 mm⁻¹
c = 14.7427 (14) Å	T = 292 K
α = 79.513 (7)°	0.30 × 0.30 × 0.19 mm
β = 83.861 (7)°

Data collection top

Oxford Diffraction Gemini/EOS CCD diffractometer	3569 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008)	2940 reflections with I > 2σ(I)
T_min = 0.840, T_max = 0.890	R_int = 0.023
5843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
3569 reflections	Δρ_min = −0.20 e Å⁻³
246 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.19042 (19)	0.58843 (14)	0.01925 (7)	0.0797 (4)
N1	0.36331 (18)	0.27710 (16)	0.60754 (8)	0.0591 (3)
H1	0.465 (2)	0.295 (2)	0.5801 (12)	0.070 (5)*
N2	0.10070 (17)	0.19149 (16)	0.60104 (8)	0.0565 (3)
H2	0.027 (2)	0.170 (2)	0.5698 (12)	0.066 (5)*
N3	0.2463 (3)	0.7821 (3)	0.50695 (14)	0.1157 (7)
C1	0.2221 (2)	0.49942 (17)	0.10443 (9)	0.0541 (3)
C2	0.1430 (2)	0.57618 (17)	0.17864 (10)	0.0579 (4)
H2A	0.0739	0.6816	0.1677	0.069*
C3	0.16593 (19)	0.49800 (17)	0.26764 (9)	0.0534 (3)
H3	0.1121	0.5512	0.3164	0.064*
C4	0.26887 (17)	0.33940 (16)	0.28649 (9)	0.0469 (3)
C5	0.34737 (19)	0.26561 (17)	0.21182 (9)	0.0550 (4)
H5	0.4168	0.1603	0.2227	0.066*
C6	0.3260 (2)	0.34347 (18)	0.12137 (10)	0.0577 (4)
H6	0.3811	0.2912	0.0725	0.069*
C7	0.2448 (3)	0.5081 (3)	−0.05893 (11)	0.0848 (6)
H7A	0.3710	0.4773	−0.0645	0.127*
H7B	0.2041	0.5813	−0.1137	0.127*
H7C	0.1961	0.4116	−0.0514	0.127*
C8	0.29403 (18)	0.25000 (17)	0.38074 (9)	0.0518 (3)
H8	0.3531	0.1408	0.3858	0.062*
C9	0.2431 (2)	0.30587 (18)	0.45874 (10)	0.0599 (4)
H9	0.1876	0.4158	0.4560	0.072*
C10	0.26927 (19)	0.20271 (18)	0.55165 (9)	0.0550 (4)
H10	0.3362	0.0925	0.5446	0.066*
C11	0.37511 (18)	0.20595 (16)	0.70001 (9)	0.0495 (3)
C12	0.5038 (2)	0.22395 (19)	0.75213 (11)	0.0616 (4)
H12	0.5903	0.2804	0.7247	0.074*
C13	0.5045 (2)	0.1575 (2)	0.84619 (11)	0.0668 (4)
H13	0.5919	0.1710	0.8805	0.080*
C14	0.3811 (2)	0.0739 (2)	0.88851 (10)	0.0625 (4)
H14	0.3848	0.0307	0.9511	0.075*
C15	0.24639 (18)	0.05219 (16)	0.83788 (9)	0.0526 (3)
C16	0.1127 (2)	−0.03118 (19)	0.87873 (11)	0.0644 (4)
H16	0.1144	−0.0795	0.9407	0.077*
C17	−0.0188 (2)	−0.0412 (2)	0.82776 (12)	0.0684 (4)
H17	−0.1062	−0.0964	0.8555	0.082*
C18	−0.02515 (19)	0.03028 (19)	0.73418 (11)	0.0608 (4)
H18	−0.1172	0.0235	0.7009	0.073*
C19	0.10345 (17)	0.10989 (16)	0.69160 (9)	0.0489 (3)
C20	0.24349 (16)	0.12050 (15)	0.74293 (9)	0.0460 (3)
C21	0.2512 (3)	0.6594 (2)	0.67886 (14)	0.0835 (5)
H21A	0.3480	0.5668	0.6877	0.125*
H21B	0.1430	0.6246	0.7000	0.125*
H21C	0.2655	0.7410	0.7134	0.125*
C22	0.2473 (2)	0.7278 (2)	0.58287 (14)	0.0749 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1225 (10)	0.0607 (7)	0.0433 (6)	−0.0013 (6)	0.0027 (6)	−0.0027 (5)
N1	0.0629 (8)	0.0651 (8)	0.0494 (7)	−0.0174 (6)	−0.0017 (6)	−0.0063 (6)
N2	0.0556 (7)	0.0655 (8)	0.0475 (7)	−0.0064 (5)	−0.0112 (5)	−0.0100 (5)
N3	0.1015 (14)	0.168 (2)	0.0829 (13)	−0.0474 (14)	−0.0207 (10)	−0.0021 (13)
C1	0.0677 (8)	0.0491 (7)	0.0437 (7)	−0.0121 (6)	0.0009 (6)	−0.0056 (6)
C2	0.0710 (9)	0.0436 (7)	0.0528 (8)	0.0004 (6)	−0.0005 (7)	−0.0093 (6)
C3	0.0616 (8)	0.0503 (7)	0.0460 (7)	−0.0042 (6)	0.0024 (6)	−0.0147 (6)
C4	0.0472 (7)	0.0477 (7)	0.0460 (7)	−0.0083 (5)	−0.0015 (5)	−0.0112 (5)
C5	0.0619 (8)	0.0473 (7)	0.0508 (8)	0.0012 (6)	−0.0017 (6)	−0.0116 (6)
C6	0.0690 (9)	0.0543 (8)	0.0473 (7)	−0.0054 (6)	0.0059 (6)	−0.0168 (6)
C7	0.1177 (16)	0.0847 (12)	0.0441 (9)	−0.0088 (11)	0.0010 (9)	−0.0093 (8)
C8	0.0534 (7)	0.0503 (7)	0.0492 (7)	−0.0039 (6)	−0.0049 (6)	−0.0095 (6)
C9	0.0728 (9)	0.0531 (8)	0.0477 (8)	−0.0005 (7)	−0.0048 (7)	−0.0079 (6)
C10	0.0624 (8)	0.0534 (8)	0.0449 (7)	−0.0015 (6)	−0.0043 (6)	−0.0096 (6)
C11	0.0507 (7)	0.0481 (7)	0.0464 (7)	−0.0012 (5)	−0.0034 (5)	−0.0108 (5)
C12	0.0558 (8)	0.0629 (9)	0.0677 (9)	−0.0096 (7)	−0.0083 (7)	−0.0157 (7)
C13	0.0647 (9)	0.0715 (10)	0.0651 (9)	0.0021 (8)	−0.0226 (7)	−0.0230 (8)
C14	0.0692 (9)	0.0649 (9)	0.0459 (7)	0.0092 (7)	−0.0135 (7)	−0.0127 (6)
C15	0.0569 (8)	0.0471 (7)	0.0455 (7)	0.0080 (6)	−0.0027 (6)	−0.0097 (5)
C16	0.0738 (10)	0.0573 (8)	0.0506 (8)	−0.0005 (7)	0.0061 (7)	−0.0015 (6)
C17	0.0660 (9)	0.0624 (9)	0.0722 (10)	−0.0144 (7)	0.0123 (8)	−0.0081 (8)
C18	0.0531 (8)	0.0610 (9)	0.0688 (9)	−0.0100 (6)	−0.0021 (7)	−0.0154 (7)
C19	0.0499 (7)	0.0450 (7)	0.0481 (7)	0.0011 (5)	−0.0038 (5)	−0.0119 (5)
C20	0.0474 (7)	0.0419 (6)	0.0443 (7)	0.0033 (5)	−0.0029 (5)	−0.0111 (5)
C21	0.0940 (13)	0.0738 (11)	0.0794 (12)	−0.0137 (10)	0.0011 (10)	−0.0126 (9)
C22	0.0647 (10)	0.0877 (12)	0.0764 (12)	−0.0204 (9)	−0.0083 (8)	−0.0161 (10)

Geometric parameters (Å, º) top

O1—C1	1.3581 (16)	C9—C10	1.4917 (19)
O1—C7	1.422 (2)	C9—H9	0.9300
N1—C11	1.3902 (17)	C10—H10	0.9800
N1—C10	1.4630 (19)	C11—C12	1.379 (2)
N1—H1	0.882 (18)	C11—C20	1.4170 (19)
N2—C19	1.3869 (17)	C12—C13	1.398 (2)
N2—C10	1.4489 (19)	C12—H12	0.9300
N2—H2	0.842 (18)	C13—C14	1.355 (2)
N3—C22	1.130 (2)	C13—H13	0.9300
C1—C6	1.381 (2)	C14—C15	1.415 (2)
C1—C2	1.3913 (19)	C14—H14	0.9300
C2—C3	1.3685 (19)	C15—C16	1.412 (2)
C2—H2A	0.9300	C15—C20	1.4144 (18)
C3—C4	1.3983 (19)	C16—C17	1.362 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.3830 (18)	C17—C18	1.403 (2)
C4—C8	1.4666 (18)	C17—H17	0.9300
C5—C6	1.3852 (19)	C18—C19	1.368 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.4226 (19)
C7—H7A	0.9600	C21—C22	1.429 (3)
C7—H7B	0.9600	C21—H21A	0.9600
C7—H7C	0.9600	C21—H21B	0.9600
C8—C9	1.312 (2)	C21—H21C	0.9600
C8—H8	0.9300

C1—O1—C7	118.12 (13)	N2—C10—H10	109.7
C11—N1—C10	116.49 (12)	N1—C10—H10	109.7
C11—N1—H1	113.1 (11)	C9—C10—H10	109.7
C10—N1—H1	112.6 (11)	C12—C11—N1	122.29 (14)
C19—N2—C10	116.97 (11)	C12—C11—C20	119.28 (13)
C19—N2—H2	114.5 (12)	N1—C11—C20	118.32 (12)
C10—N2—H2	114.7 (12)	C11—C12—C13	120.18 (15)
O1—C1—C6	125.11 (13)	C11—C12—H12	119.9
O1—C1—C2	115.59 (13)	C13—C12—H12	119.9
C6—C1—C2	119.30 (13)	C14—C13—C12	121.58 (14)
C3—C2—C1	120.63 (13)	C14—C13—H13	119.2
C3—C2—H2A	119.7	C12—C13—H13	119.2
C1—C2—H2A	119.7	C13—C14—C15	120.31 (14)
C2—C3—C4	121.10 (12)	C13—C14—H14	119.8
C2—C3—H3	119.5	C15—C14—H14	119.8
C4—C3—H3	119.5	C16—C15—C20	118.76 (13)
C5—C4—C3	117.41 (12)	C16—C15—C14	122.73 (14)
C5—C4—C8	119.73 (12)	C20—C15—C14	118.49 (14)
C3—C4—C8	122.85 (12)	C17—C16—C15	120.21 (14)
C4—C5—C6	122.15 (12)	C17—C16—H16	119.9
C4—C5—H5	118.9	C15—C16—H16	119.9
C6—C5—H5	118.9	C16—C17—C18	121.29 (15)
C1—C6—C5	119.41 (13)	C16—C17—H17	119.4
C1—C6—H6	120.3	C18—C17—H17	119.4
C5—C6—H6	120.3	C19—C18—C17	120.33 (14)
O1—C7—H7A	109.5	C19—C18—H18	119.8
O1—C7—H7B	109.5	C17—C18—H18	119.8
H7A—C7—H7B	109.5	C18—C19—N2	123.57 (13)
O1—C7—H7C	109.5	C18—C19—C20	119.56 (13)
H7A—C7—H7C	109.5	N2—C19—C20	116.74 (12)
H7B—C7—H7C	109.5	C15—C20—C11	120.15 (12)
C9—C8—C4	127.69 (13)	C15—C20—C19	119.81 (13)
C9—C8—H8	116.2	C11—C20—C19	119.98 (12)
C4—C8—H8	116.2	C22—C21—H21A	109.5
C8—C9—C10	123.58 (14)	C22—C21—H21B	109.5
C8—C9—H9	118.2	H21A—C21—H21B	109.5
C10—C9—H9	118.2	C22—C21—H21C	109.5
N2—C10—N1	106.95 (11)	H21A—C21—H21C	109.5
N2—C10—C9	110.23 (12)	H21B—C21—H21C	109.5
N1—C10—C9	110.56 (12)	N3—C22—C21	179.1 (2)

C7—O1—C1—C6	10.1 (3)	C11—C12—C13—C14	0.2 (2)
C7—O1—C1—C2	−170.59 (16)	C12—C13—C14—C15	−0.2 (2)
O1—C1—C2—C3	−179.98 (14)	C13—C14—C15—C16	−178.84 (14)
C6—C1—C2—C3	−0.7 (2)	C13—C14—C15—C20	−0.5 (2)
C1—C2—C3—C4	−0.1 (2)	C20—C15—C16—C17	−1.8 (2)
C2—C3—C4—C5	0.5 (2)	C14—C15—C16—C17	176.61 (14)
C2—C3—C4—C8	−178.77 (13)	C15—C16—C17—C18	0.0 (2)
C3—C4—C5—C6	−0.2 (2)	C16—C17—C18—C19	1.0 (2)
C8—C4—C5—C6	179.08 (13)	C17—C18—C19—N2	−176.13 (13)
O1—C1—C6—C5	−179.82 (14)	C17—C18—C19—C20	−0.3 (2)
C2—C1—C6—C5	0.9 (2)	C10—N2—C19—C18	−152.05 (14)
C4—C5—C6—C1	−0.5 (2)	C10—N2—C19—C20	31.99 (17)
C5—C4—C8—C9	173.37 (16)	C16—C15—C20—C11	179.55 (12)
C3—C4—C8—C9	−7.4 (2)	C14—C15—C20—C11	1.10 (19)
C4—C8—C9—C10	177.61 (13)	C16—C15—C20—C19	2.48 (18)
C19—N2—C10—N1	−54.88 (16)	C14—C15—C20—C19	−175.97 (12)
C19—N2—C10—C9	−175.12 (11)	C12—C11—C20—C15	−1.08 (19)
C11—N1—C10—N2	51.33 (16)	N1—C11—C20—C15	−177.36 (11)
C11—N1—C10—C9	171.35 (12)	C12—C11—C20—C19	175.98 (12)
C8—C9—C10—N2	−116.90 (17)	N1—C11—C20—C19	−0.30 (19)
C8—C9—C10—N1	125.05 (16)	C18—C19—C20—C15	−1.48 (19)
C10—N1—C11—C12	157.87 (14)	N2—C19—C20—C15	174.65 (11)
C10—N1—C11—C20	−25.97 (18)	C18—C19—C20—C11	−178.55 (12)
N1—C11—C12—C13	176.53 (13)	N2—C19—C20—C11	−2.42 (18)
C20—C11—C12—C13	0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.88 (2)	2.49 (2)	3.305 (3)	154.1 (15)
N2—H2···N3ⁱⁱ	0.84 (2)	2.44 (2)	3.234 (2)	156.8 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.88 (2)	2.49 (2)	3.305 (3)	154.1 (15)
N2—H2···N3ⁱⁱ	0.84 (2)	2.44 (2)	3.234 (2)	156.8 (16)

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

Acknowledgements

We are grateful to IICT, Hyderabad, for support of the instrumentation facility.

References

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Volume 70| Part 9| September 2014| Page o959

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-2-(4-meth­­oxy­styr­yl)-2,3-di­hydro-1H-perimidine aceto­nitrile monosolvate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate