7-Di-ethyl-amino-3-{(E)-4-[(E)-2-(pyridin-4-yl)ethen-yl]styr-yl}-2H-chromen-2-one.

In the title coumarin derivative, C28H26N2O2, the coumarin unit is approximately planar, with a maximum deviation of 0.048 (3) Å. The central benzene ring is oriented at dihedral angles of 30.15 (14) and 10.51 (11)°, respectively, to the pyridine ring and coumarin ring system. In the crystal, weak C-H⋯O and C-H⋯N hydrogen bonds and weak C-H⋯π inter-actions link the mol-ecules into a three-dimensional supra-molecular architecture.

Related literature

For applications of coumarin derivatives, see: Gong et al. (2012 ▶); Jones et al. (1985 ▶); Nemkovich et al. (1997 ▶); Jin et al. (2011 ▶); Helal et al. (2011 ▶).

Experimental

Crystal data

C28H26N2O2

M = 422.51

Monoclinic,

a = 15.511 (3) Å

b = 8.4745 (17) Å

c = 16.882 (7) Å

β = 97.73 (3)°

V = 2198.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.27 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

9607 measured reflections

3931 independent reflections

2993 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.170

S = 1.13

3931 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814001123/xu5763sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001123/xu5763Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001123/xu5763Isup3.cml

CCDC reference:

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

C28H26N2O2	F(000) = 896
Mr = 422.51	Dx = 1.276 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9607 reflections
a = 15.511 (3) Å	θ = 3.5–25.5°
b = 8.4745 (17) Å	µ = 0.08 mm−1
c = 16.882 (7) Å	T = 293 K
β = 97.73 (3)°	Block, pink
V = 2198.9 (11) Å3	0.27 × 0.25 × 0.23 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 25.2°, θmin = 3.6°
phi and ω scans	h = −16→18
9607 measured reflections	k = −10→8
3931 independent reflections	l = −18→20

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.054P)2 + 1.2201P] where P = (Fo2 + 2Fc2)/3
3931 reflections	(Δ/σ)max = 0.004
291 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. 1H NMR (400MHz, CDCl3) δ (ppm): 8.60 (d, J = 6.0 Hz, 2H), 7.72 (s, 1H), 7.53 (m, 7H), 7.41(d, J = 16.0 Hz, 1H), 7.33 (d, J = 9.0 Hz, 1H), 7.19 (d, J = 16.4 Hz, 1H), 7.09 (d, J = 16.4 Hz, 1H), 6.64 (dd, J1 = 2.4 Hz, J2 = 8.8 Hz, 1H), 6.54 (d, J = 2.4 Hz, 1H), 3.48 (q, J = 7.2 Hz, 4H), 1.27 (t, J = 7.2 Hz, 6H). ESI-MS (m/z): 423.3 [M+1]+. Anal. calcd for C28H26N2O2: C 79.59, H 6.20, N 6.63; found C 79.34, H 6.23, N 6.61.

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.

	x	y	z	Uiso*/Ueq
N1	1.47594 (15)	0.3672 (3)	0.89342 (16)	0.0470 (7)
N2	0.22420 (13)	0.3446 (3)	0.48620 (14)	0.0365 (6)
O1	0.65839 (12)	0.1130 (3)	0.54400 (15)	0.0588 (7)
O2	0.52260 (11)	0.1909 (2)	0.53258 (13)	0.0415 (5)
C1	1.40807 (18)	0.4019 (4)	0.93132 (19)	0.0498 (8)
H1	1.4196	0.4368	0.9839	0.060*
C2	1.32252 (18)	0.3898 (4)	0.89825 (19)	0.0457 (8)
H2	1.2783	0.4147	0.9283	0.055*
C3	1.30236 (17)	0.3397 (3)	0.81916 (17)	0.0362 (7)
C4	1.37250 (17)	0.3025 (3)	0.77916 (19)	0.0411 (7)
H4	1.3631	0.2676	0.7265	0.049*
C5	1.45611 (18)	0.3177 (4)	0.8182 (2)	0.0461 (8)
H5	1.5018	0.2916	0.7901	0.055*
C6	1.21301 (17)	0.3227 (3)	0.77934 (18)	0.0383 (7)
H6	1.2052	0.2639	0.7324	0.046*
C7	1.14170 (17)	0.3832 (3)	0.80373 (17)	0.0372 (7)
H7	1.1497	0.4475	0.8487	0.045*
C8	1.05196 (17)	0.3579 (3)	0.76635 (17)	0.0359 (7)
C9	1.02959 (17)	0.2394 (4)	0.70924 (17)	0.0386 (7)
H9	1.0731	0.1758	0.6934	0.046*
C10	0.94475 (17)	0.2154 (3)	0.67630 (17)	0.0385 (7)
H10	0.9321	0.1348	0.6392	0.046*
C11	0.87729 (17)	0.3078 (3)	0.69667 (17)	0.0369 (7)
C12	0.89826 (17)	0.4242 (4)	0.75531 (18)	0.0418 (8)
H12	0.8545	0.4864	0.7716	0.050*
C13	0.98422 (17)	0.4470 (4)	0.78924 (19)	0.0430 (7)
H13	0.9967	0.5240	0.8283	0.052*
C14	0.78861 (18)	0.2774 (3)	0.65598 (18)	0.0404 (7)
H14	0.7806	0.1860	0.6254	0.048*
C15	0.71960 (18)	0.3667 (3)	0.65861 (18)	0.0404 (7)
H15	0.7285	0.4568	0.6901	0.048*
C16	0.63081 (17)	0.3435 (3)	0.61866 (17)	0.0353 (7)
C17	0.60931 (17)	0.2112 (3)	0.5649 (2)	0.0409 (7)
C18	0.45869 (16)	0.2969 (3)	0.54637 (17)	0.0336 (7)
C19	0.48051 (17)	0.4303 (3)	0.59359 (16)	0.0342 (7)
C20	0.56747 (17)	0.4488 (3)	0.62915 (17)	0.0372 (7)
H20	0.5820	0.5368	0.6611	0.045*
C21	0.37542 (16)	0.2645 (3)	0.51058 (17)	0.0342 (7)
H21	0.3639	0.1734	0.4803	0.041*
C22	0.30769 (17)	0.3713 (3)	0.52046 (16)	0.0339 (7)
C23	0.32947 (18)	0.5082 (4)	0.56701 (17)	0.0400 (7)
H23	0.2862	0.5807	0.5743	0.048*
C24	0.41301 (18)	0.5355 (4)	0.60136 (17)	0.0417 (7)
H24	0.4253	0.6273	0.6309	0.050*
C25	0.19833 (18)	0.1976 (3)	0.44438 (18)	0.0395 (7)
H25A	0.1384	0.1744	0.4508	0.047*
H25B	0.2342	0.1124	0.4688	0.047*
C26	0.15537 (17)	0.4615 (4)	0.48859 (17)	0.0393 (7)
H26A	0.1134	0.4510	0.4408	0.047*
H26B	0.1805	0.5663	0.4884	0.047*
C27	0.2064 (2)	0.2034 (4)	0.35653 (19)	0.0475 (8)
H27A	0.1715	0.2883	0.3320	0.071*
H27B	0.1867	0.1054	0.3320	0.071*
H27C	0.2661	0.2203	0.3497	0.071*
C28	0.1087 (2)	0.4444 (5)	0.56134 (19)	0.0551 (9)
H28A	0.0833	0.3411	0.5617	0.083*
H28B	0.0638	0.5227	0.5596	0.083*
H28C	0.1495	0.4586	0.6089	0.083*

	U11	U22	U33	U12	U13	U23
N1	0.0280 (13)	0.0560 (17)	0.0546 (17)	−0.0014 (12)	−0.0031 (12)	0.0004 (14)
N2	0.0246 (12)	0.0407 (14)	0.0425 (14)	0.0028 (10)	−0.0018 (10)	0.0017 (11)
O1	0.0295 (11)	0.0415 (12)	0.101 (2)	0.0045 (10)	−0.0078 (12)	−0.0150 (13)
O2	0.0244 (10)	0.0315 (10)	0.0654 (14)	0.0001 (8)	−0.0053 (9)	−0.0033 (10)
C1	0.0315 (16)	0.070 (2)	0.0445 (19)	−0.0033 (16)	−0.0056 (14)	−0.0094 (17)
C2	0.0290 (15)	0.060 (2)	0.0471 (19)	−0.0009 (15)	0.0003 (13)	−0.0041 (16)
C3	0.0280 (14)	0.0391 (16)	0.0396 (17)	−0.0045 (12)	−0.0025 (12)	0.0014 (13)
C4	0.0333 (16)	0.0456 (17)	0.0434 (18)	−0.0023 (14)	0.0012 (13)	−0.0022 (15)
C5	0.0284 (15)	0.054 (2)	0.055 (2)	0.0012 (14)	0.0033 (14)	−0.0022 (17)
C6	0.0306 (15)	0.0446 (17)	0.0378 (17)	−0.0034 (13)	−0.0018 (13)	0.0003 (14)
C7	0.0282 (14)	0.0413 (17)	0.0399 (17)	−0.0038 (13)	−0.0037 (12)	0.0026 (13)
C8	0.0279 (14)	0.0412 (16)	0.0372 (17)	−0.0009 (13)	−0.0003 (12)	0.0106 (13)
C9	0.0251 (14)	0.0488 (18)	0.0407 (17)	−0.0015 (13)	−0.0006 (12)	0.0032 (14)
C10	0.0340 (15)	0.0440 (17)	0.0358 (17)	−0.0020 (14)	−0.0015 (13)	0.0039 (13)
C11	0.0305 (15)	0.0434 (17)	0.0351 (16)	−0.0067 (13)	−0.0014 (12)	0.0109 (14)
C12	0.0260 (14)	0.0458 (18)	0.054 (2)	0.0030 (13)	0.0052 (13)	0.0096 (15)
C13	0.0323 (15)	0.0440 (17)	0.0508 (19)	−0.0018 (14)	−0.0015 (14)	0.0001 (15)
C14	0.0364 (16)	0.0374 (16)	0.0467 (18)	−0.0047 (14)	0.0030 (14)	0.0050 (14)
C15	0.0360 (16)	0.0392 (17)	0.0450 (18)	−0.0033 (14)	0.0022 (14)	0.0058 (14)
C16	0.0277 (14)	0.0407 (16)	0.0357 (16)	−0.0067 (13)	−0.0022 (12)	0.0071 (13)
C17	0.0223 (14)	0.0345 (16)	0.064 (2)	0.0040 (13)	−0.0026 (14)	0.0067 (15)
C18	0.0237 (14)	0.0319 (15)	0.0438 (17)	0.0016 (12)	−0.0013 (12)	0.0048 (13)
C19	0.0298 (14)	0.0383 (16)	0.0332 (16)	−0.0022 (13)	−0.0004 (12)	0.0003 (13)
C20	0.0322 (15)	0.0419 (17)	0.0360 (16)	−0.0060 (13)	−0.0007 (12)	−0.0046 (13)
C21	0.0263 (14)	0.0293 (14)	0.0452 (17)	−0.0011 (12)	−0.0017 (12)	−0.0004 (12)
C22	0.0280 (14)	0.0425 (16)	0.0307 (16)	0.0013 (13)	0.0024 (12)	0.0027 (12)
C23	0.0328 (15)	0.0473 (18)	0.0391 (17)	0.0055 (14)	0.0012 (13)	−0.0076 (14)
C24	0.0404 (17)	0.0456 (18)	0.0382 (17)	−0.0020 (15)	0.0022 (13)	−0.0134 (14)
C25	0.0267 (14)	0.0379 (16)	0.0518 (19)	−0.0036 (13)	−0.0022 (13)	0.0041 (14)
C26	0.0275 (14)	0.0515 (18)	0.0383 (17)	0.0093 (14)	0.0022 (12)	0.0031 (14)
C27	0.0424 (17)	0.0476 (19)	0.051 (2)	−0.0014 (15)	0.0002 (15)	−0.0026 (15)
C28	0.0389 (17)	0.081 (3)	0.047 (2)	0.0071 (17)	0.0121 (15)	0.0084 (18)

N1—C5	1.334 (4)	C13—H13	0.9300
N1—C1	1.336 (4)	C14—C15	1.317 (4)
N2—C22	1.364 (3)	C14—H14	0.9300
N2—C25	1.461 (4)	C15—C16	1.463 (4)
N2—C26	1.461 (3)	C15—H15	0.9300
O1—C17	1.212 (3)	C16—C20	1.356 (4)
O2—C18	1.381 (3)	C16—C17	1.453 (4)
O2—C17	1.392 (3)	C18—C21	1.378 (4)
C1—C2	1.372 (4)	C18—C19	1.398 (4)
C1—H1	0.9300	C19—C24	1.395 (4)
C2—C3	1.396 (4)	C19—C20	1.409 (4)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.392 (4)	C21—C22	1.413 (4)
C3—C6	1.464 (4)	C21—H21	0.9300
C4—C5	1.379 (4)	C22—C23	1.417 (4)
C4—H4	0.9300	C23—C24	1.366 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.333 (4)	C24—H24	0.9300
C6—H6	0.9300	C25—C27	1.506 (4)
C7—C8	1.465 (4)	C25—H25A	0.9700
C7—H7	0.9300	C25—H25B	0.9700
C8—C13	1.390 (4)	C26—C28	1.514 (4)
C8—C9	1.403 (4)	C26—H26A	0.9700
C9—C10	1.373 (4)	C26—H26B	0.9700
C9—H9	0.9300	C27—H27A	0.9600
C10—C11	1.387 (4)	C27—H27B	0.9600
C10—H10	0.9300	C27—H27C	0.9600
C11—C12	1.404 (4)	C28—H28A	0.9600
C11—C14	1.475 (4)	C28—H28B	0.9600
C12—C13	1.392 (4)	C28—H28C	0.9600
C12—H12	0.9300
C5—N1—C1	115.4 (3)	C20—C16—C15	120.3 (3)
C22—N2—C25	122.0 (2)	C17—C16—C15	121.0 (3)
C22—N2—C26	122.1 (2)	O1—C17—O2	114.4 (3)
C25—N2—C26	115.9 (2)	O1—C17—C16	127.7 (3)
C18—O2—C17	122.1 (2)	O2—C17—C16	117.9 (2)
N1—C1—C2	124.7 (3)	C21—C18—O2	116.6 (2)
N1—C1—H1	117.6	C21—C18—C19	123.5 (3)
C2—C1—H1	117.6	O2—C18—C19	119.9 (2)
C1—C2—C3	119.5 (3)	C24—C19—C18	116.3 (2)
C1—C2—H2	120.3	C24—C19—C20	125.2 (3)
C3—C2—H2	120.3	C18—C19—C20	118.5 (3)
C4—C3—C2	116.3 (3)	C16—C20—C19	122.7 (3)
C4—C3—C6	120.6 (3)	C16—C20—H20	118.7
C2—C3—C6	123.1 (3)	C19—C20—H20	118.7
C5—C4—C3	119.6 (3)	C18—C21—C22	119.2 (3)
C5—C4—H4	120.2	C18—C21—H21	120.4
C3—C4—H4	120.2	C22—C21—H21	120.4
N1—C5—C4	124.4 (3)	N2—C22—C21	121.4 (3)
N1—C5—H5	117.8	N2—C22—C23	120.9 (2)
C4—C5—H5	117.8	C21—C22—C23	117.7 (2)
C7—C6—C3	126.4 (3)	C24—C23—C22	121.1 (3)
C7—C6—H6	116.8	C24—C23—H23	119.5
C3—C6—H6	116.8	C22—C23—H23	119.5
C6—C7—C8	126.2 (3)	C23—C24—C19	122.2 (3)
C6—C7—H7	116.9	C23—C24—H24	118.9
C8—C7—H7	116.9	C19—C24—H24	118.9
C13—C8—C9	117.0 (3)	N2—C25—C27	113.2 (2)
C13—C8—C7	120.7 (3)	N2—C25—H25A	108.9
C9—C8—C7	122.3 (3)	C27—C25—H25A	108.9
C10—C9—C8	121.3 (3)	N2—C25—H25B	108.9
C10—C9—H9	119.4	C27—C25—H25B	108.9
C8—C9—H9	119.4	H25A—C25—H25B	107.7
C9—C10—C11	122.0 (3)	N2—C26—C28	112.9 (2)
C9—C10—H10	119.0	N2—C26—H26A	109.0
C11—C10—H10	119.0	C28—C26—H26A	109.0
C10—C11—C12	117.4 (3)	N2—C26—H26B	109.0
C10—C11—C14	118.2 (3)	C28—C26—H26B	109.0
C12—C11—C14	124.3 (3)	H26A—C26—H26B	107.8
C13—C12—C11	120.4 (3)	C25—C27—H27A	109.5
C13—C12—H12	119.8	C25—C27—H27B	109.5
C11—C12—H12	119.8	H27A—C27—H27B	109.5
C8—C13—C12	121.9 (3)	C25—C27—H27C	109.5
C8—C13—H13	119.1	H27A—C27—H27C	109.5
C12—C13—H13	119.1	H27B—C27—H27C	109.5
C15—C14—C11	126.5 (3)	C26—C28—H28A	109.5
C15—C14—H14	116.7	C26—C28—H28B	109.5
C11—C14—H14	116.7	H28A—C28—H28B	109.5
C14—C15—C16	128.8 (3)	C26—C28—H28C	109.5
C14—C15—H15	115.6	H28A—C28—H28C	109.5
C16—C15—H15	115.6	H28B—C28—H28C	109.5
C20—C16—C17	118.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1i	0.93	2.48	3.351 (4)	156
C25—H25A···N1ii	0.97	2.60	3.485 (4)	152
C25—H25B···O1i	0.97	2.56	3.433 (4)	150
C9—H9···Cg2iii	0.93	2.94	3.728 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1i	0.93	2.48	3.351 (4)	156
C25—H25A⋯N1ii	0.97	2.60	3.485 (4)	152
C25—H25B⋯O1i	0.97	2.56	3.433 (4)	150
C9—H9⋯Cg2iii	0.93	2.94	3.728 (4)	143

Symmetry codes: (i) ; (ii) ; (iii) .