Crystal structure of (E)-2-(4-meth-oxy-styr-yl)-2,3-di-hydro-1H-perimidine aceto-nitrile monosolvate.

The title compound, C20H18N2O·CH3CN, a perimidine deriv-ative, crystallized as an aceto-nitrile monosolvate. The planes of the naphthalene ring system and the meth-oxy-phenyl 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 hexa-hydro-pyrimidine ring has an envelope conformation, with the methine C atom as the flap. In the crystal, the mol-ecules are linked by N-H⋯N hydrogen bonds involving the aceto-nitrile solvent mol-ecule as acceptor, forming zigzag chains propagating along [100].

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 ▶).

Experimental

Crystal data

C20H18N2O·C2H3N

M = 343.42

Triclinic,

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

Data collection

Oxford Diffraction Gemini/EOS CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008 ▶) T min = 0.840, T max = 0.890

5843 measured reflections

3569 independent reflections

2940 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.03

3569 reflections

246 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814017000/su2762sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S1600536814017000/su2762fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814017000/su2762fig2.tif

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).

CCDC reference: 1015577

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H18N2O·C2H3N	Z = 2
Mr = 343.42	F(000) = 364
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0768P)2 + 0.0999P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3569 reflections	Δρmax = 0.19 e Å−3
246 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) ; (ii) .