4'-Cyano-biphenyl-4-yl 7-diethyl-amino-2-oxo-2H-chromene-3-carboxyl-ate.

In the title compound, C(27)H(22)N(2)O(4), the dihedral angles between the central benzene ring and the cyano-benzene ring and the 2H-coumarin ring system (r.m.s. deviation = 0.014 Å) are 22.95 (11) and 75.59 (8)°, respectively. Both terminal C atoms of the pendant diethyl-amino group lie to the same side of the coumarin ring system [deviations = 1.366 (2) and 1.266 (2) Å]. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds and a C-H⋯π inter-action, generating a three-dimensional network.

Related literature

For the biological properties of coumarin derivatives, see: Bhat et al. (2006 ▶); Chimichi et al. (2002 ▶).

Experimental

Crystal data

C27H22N2O4

M = 438.47

Triclinic,

a = 9.652 (3) Å

b = 10.252 (4) Å

c = 11.121 (4) Å

α = 87.214 (10)°

β = 86.358 (10)°

γ = 84.348 (11)°

V = 1091.9 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 300 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.979, T max = 0.984

10667 measured reflections

3783 independent reflections

2495 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.173

S = 0.97

3783 reflections

301 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001591/hb7027sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001591/hb7027Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001591/hb7027Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H22N2O4	Z = 2
Mr = 438.47	F(000) = 460
Triclinic, P1	Dx = 1.334 Mg m−3
Hall symbol: -P 1	Melting point: 541 K
a = 9.652 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.252 (4) Å	Cell parameters from 3783 reflections
c = 11.121 (4) Å	θ = 1.8–25.0°
α = 87.214 (10)°	µ = 0.09 mm−1
β = 86.358 (10)°	T = 300 K
γ = 84.348 (11)°	Prism, colourless
V = 1091.9 (6) Å3	0.24 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	3783 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω and φ scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→10
Tmin = 0.979, Tmax = 0.984	k = −12→12
10667 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.1107P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
3783 reflections	Δρmax = 0.22 e Å−3
301 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Experimental. 1H NMR (400Mz, TMS): δ 8.36(s, 1H), 7.44–7.65(m, 6H), 7.12–7.08(m, 3H), 6.34(m, 2H), 3.38(m, 4H), 1.10(m, 6H); Elemental analysis calculated for C27H22N2O4, C, 73.96; H, 5.06; N, 6.39; found C, 74.20; H, 5.32; N, 6.33.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.24765 (18)	1.10054 (17)	0.94063 (14)	0.0535 (5)
O2	0.37525 (15)	0.91308 (15)	0.92731 (12)	0.0417 (4)
O3	−0.04165 (16)	0.96402 (16)	0.71953 (13)	0.0503 (5)
O4	−0.0195 (2)	1.1161 (2)	0.85320 (18)	0.0753 (6)
N1	0.68882 (19)	0.52702 (19)	0.90485 (16)	0.0457 (5)
N2	−1.0656 (2)	1.3764 (2)	0.4192 (2)	0.0641 (7)
C1	0.7967 (3)	0.4011 (3)	0.7316 (2)	0.0668 (8)
H1A	0.7313	0.4453	0.6782	0.100*
H1B	0.8213	0.3130	0.7068	0.100*
H1C	0.8789	0.4469	0.7291	0.100*
C2	0.7317 (3)	0.3978 (2)	0.8581 (2)	0.0493 (6)
H2A	0.6507	0.3485	0.8602	0.059*
H2B	0.7980	0.3515	0.9109	0.059*
C3	0.7847 (3)	0.5811 (3)	0.9826 (2)	0.0529 (7)
H3A	0.8333	0.5094	1.0280	0.064*
H3B	0.7308	0.6370	1.0399	0.064*
C4	0.8898 (3)	0.6584 (3)	0.9148 (2)	0.0656 (8)
H4A	0.9469	0.6026	0.8608	0.098*
H4B	0.9474	0.6927	0.9706	0.098*
H4C	0.8426	0.7296	0.8695	0.098*
C5	0.4066 (2)	0.7908 (2)	0.88368 (16)	0.0342 (5)
C6	0.5309 (2)	0.7249 (2)	0.91367 (18)	0.0393 (6)
H6	0.5901	0.7641	0.9607	0.047*
C7	0.5690 (2)	0.5977 (2)	0.87307 (18)	0.0383 (5)
C8	0.4763 (2)	0.5447 (2)	0.7979 (2)	0.0448 (6)
H8	0.4998	0.4617	0.7681	0.054*
C9	0.3544 (2)	0.6131 (2)	0.76906 (19)	0.0425 (6)
H9	0.2965	0.5757	0.7195	0.051*
C10	0.3130 (2)	0.7385 (2)	0.81176 (17)	0.0361 (5)
C11	0.1893 (2)	0.8156 (2)	0.78679 (18)	0.0376 (5)
H11	0.1267	0.7824	0.7388	0.045*
C12	0.1576 (2)	0.9373 (2)	0.83021 (17)	0.0366 (5)
C13	0.2546 (2)	0.9931 (2)	0.90192 (18)	0.0380 (5)
C14	0.0264 (2)	1.0177 (2)	0.80661 (19)	0.0449 (6)
C15	−0.4115 (2)	1.0844 (2)	0.73193 (18)	0.0441 (6)
H15	−0.4890	1.0853	0.7861	0.053*
C16	−0.2848 (2)	1.0282 (2)	0.76805 (18)	0.0451 (6)
H16	−0.2770	0.9911	0.8456	0.054*
C17	−0.1706 (2)	1.0274 (2)	0.68882 (19)	0.0416 (6)
C18	−0.1806 (2)	1.0826 (2)	0.5739 (2)	0.0481 (6)
H18	−0.1022	1.0822	0.5208	0.058*
C19	−0.3081 (2)	1.1384 (3)	0.53862 (19)	0.0483 (6)
H19	−0.3147	1.1757	0.4610	0.058*
C20	−0.4266 (2)	1.1403 (2)	0.61565 (18)	0.0392 (6)
C21	−0.5644 (2)	1.1962 (2)	0.57555 (17)	0.0384 (5)
C22	−0.5909 (2)	1.2058 (2)	0.45324 (19)	0.0473 (6)
H22	−0.5202	1.1791	0.3964	0.057*
C23	−0.7190 (3)	1.2539 (3)	0.4155 (2)	0.0490 (6)
H23	−0.7338	1.2605	0.3336	0.059*
C24	−0.8261 (2)	1.2927 (2)	0.4976 (2)	0.0442 (6)
C25	−0.8024 (3)	1.2853 (3)	0.6196 (2)	0.0567 (7)
H25	−0.8733	1.3124	0.6761	0.068*
C26	−0.6725 (3)	1.2373 (3)	0.6565 (2)	0.0534 (7)
H26	−0.6573	1.2325	0.7384	0.064*
C27	−0.9608 (3)	1.3402 (2)	0.4561 (2)	0.0490 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0521 (11)	0.0481 (12)	0.0611 (10)	0.0095 (8)	−0.0207 (8)	−0.0165 (8)
O2	0.0338 (9)	0.0459 (10)	0.0452 (8)	0.0071 (7)	−0.0118 (7)	−0.0110 (7)
O3	0.0396 (10)	0.0559 (11)	0.0541 (9)	0.0177 (8)	−0.0193 (8)	−0.0138 (7)
O4	0.0577 (13)	0.0671 (14)	0.1019 (15)	0.0276 (10)	−0.0357 (11)	−0.0404 (11)
N1	0.0342 (12)	0.0484 (13)	0.0530 (11)	0.0099 (9)	−0.0095 (9)	−0.0056 (9)
N2	0.0480 (14)	0.0701 (17)	0.0754 (14)	0.0078 (12)	−0.0270 (12)	−0.0109 (12)
C1	0.068 (2)	0.0506 (18)	0.0788 (18)	0.0061 (14)	0.0090 (15)	−0.0119 (13)
C2	0.0434 (15)	0.0425 (15)	0.0594 (14)	0.0091 (12)	−0.0053 (11)	0.0016 (11)
C3	0.0398 (15)	0.0597 (18)	0.0569 (13)	0.0145 (12)	−0.0136 (11)	−0.0019 (12)
C4	0.0493 (18)	0.076 (2)	0.0709 (17)	0.0032 (15)	−0.0055 (13)	−0.0118 (14)
C5	0.0326 (13)	0.0376 (13)	0.0321 (10)	−0.0006 (10)	−0.0022 (9)	−0.0031 (8)
C6	0.0272 (13)	0.0503 (15)	0.0402 (11)	0.0010 (10)	−0.0060 (9)	−0.0051 (10)
C7	0.0288 (12)	0.0451 (15)	0.0392 (11)	0.0047 (10)	−0.0013 (9)	0.0000 (9)
C8	0.0362 (14)	0.0435 (15)	0.0537 (12)	0.0052 (11)	−0.0062 (10)	−0.0079 (10)
C9	0.0345 (14)	0.0462 (15)	0.0476 (12)	−0.0006 (11)	−0.0094 (10)	−0.0076 (10)
C10	0.0296 (13)	0.0418 (14)	0.0364 (10)	0.0004 (10)	−0.0047 (9)	−0.0019 (9)
C11	0.0309 (13)	0.0460 (15)	0.0363 (10)	−0.0018 (10)	−0.0079 (9)	−0.0019 (9)
C12	0.0319 (13)	0.0412 (14)	0.0361 (10)	0.0022 (10)	−0.0066 (9)	−0.0022 (9)
C13	0.0344 (13)	0.0426 (15)	0.0361 (10)	0.0045 (10)	−0.0054 (9)	−0.0042 (9)
C14	0.0419 (15)	0.0454 (16)	0.0473 (12)	0.0046 (12)	−0.0115 (11)	−0.0078 (11)
C15	0.0358 (14)	0.0542 (16)	0.0403 (11)	0.0034 (11)	−0.0019 (10)	0.0026 (10)
C16	0.0452 (16)	0.0518 (16)	0.0366 (11)	0.0054 (11)	−0.0093 (11)	0.0044 (10)
C17	0.0361 (14)	0.0406 (14)	0.0475 (12)	0.0081 (10)	−0.0137 (10)	−0.0053 (9)
C18	0.0355 (14)	0.0567 (17)	0.0491 (13)	0.0081 (12)	0.0002 (10)	0.0014 (11)
C19	0.0398 (15)	0.0617 (17)	0.0394 (11)	0.0094 (12)	−0.0030 (10)	0.0090 (10)
C20	0.0361 (13)	0.0407 (14)	0.0394 (11)	0.0044 (10)	−0.0050 (10)	0.0004 (9)
C21	0.0341 (13)	0.0407 (14)	0.0389 (11)	0.0039 (10)	−0.0047 (9)	0.0005 (9)
C22	0.0365 (14)	0.0634 (17)	0.0392 (11)	0.0073 (12)	−0.0019 (10)	−0.0004 (10)
C23	0.0471 (16)	0.0574 (17)	0.0420 (12)	0.0027 (12)	−0.0122 (11)	0.0013 (10)
C24	0.0322 (14)	0.0456 (15)	0.0544 (13)	0.0025 (11)	−0.0115 (11)	0.0003 (10)
C25	0.0391 (15)	0.078 (2)	0.0477 (13)	0.0180 (13)	−0.0009 (11)	−0.0029 (12)
C26	0.0428 (16)	0.0751 (19)	0.0386 (12)	0.0145 (13)	−0.0057 (11)	−0.0015 (11)
C27	0.0457 (16)	0.0495 (16)	0.0522 (13)	0.0011 (12)	−0.0120 (12)	−0.0058 (11)

O1—C13	1.196 (3)	C9—C10	1.404 (3)
O2—C5	1.365 (3)	C9—H9	0.9300
O2—C13	1.393 (3)	C10—C11	1.401 (3)
O3—C14	1.370 (3)	C11—C12	1.360 (3)
O3—C17	1.400 (3)	C11—H11	0.9300
O4—C14	1.189 (3)	C12—C13	1.443 (3)
N1—C7	1.360 (3)	C12—C14	1.473 (3)
N1—C2	1.459 (3)	C15—C16	1.374 (3)
N1—C3	1.470 (3)	C15—C20	1.399 (3)
N2—C27	1.138 (3)	C15—H15	0.9300
C1—C2	1.504 (4)	C16—C17	1.367 (3)
C1—H1A	0.9600	C16—H16	0.9300
C1—H1B	0.9600	C17—C18	1.378 (3)
C1—H1C	0.9600	C18—C19	1.377 (3)
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—C20	1.384 (3)
C3—C4	1.493 (4)	C19—H19	0.9300
C3—H3A	0.9700	C20—C21	1.482 (3)
C3—H3B	0.9700	C21—C26	1.381 (3)
C4—H4A	0.9600	C21—C22	1.397 (3)
C4—H4B	0.9600	C22—C23	1.368 (3)
C4—H4C	0.9600	C22—H22	0.9300
C5—C6	1.370 (3)	C23—C24	1.377 (3)
C5—C10	1.405 (3)	C23—H23	0.9300
C6—C7	1.408 (3)	C24—C25	1.388 (3)
C6—H6	0.9300	C24—C27	1.439 (3)
C7—C8	1.424 (3)	C25—C26	1.380 (3)
C8—C9	1.358 (3)	C25—H25	0.9300
C8—H8	0.9300	C26—H26	0.9300
C5—O2—C13	123.43 (16)	C12—C11—H11	118.9
C14—O3—C17	117.47 (18)	C10—C11—H11	118.9
C7—N1—C2	121.64 (19)	C11—C12—C13	120.2 (2)
C7—N1—C3	121.2 (2)	C11—C12—C14	122.59 (19)
C2—N1—C3	117.10 (19)	C13—C12—C14	117.3 (2)
C2—C1—H1A	109.5	O1—C13—O2	114.84 (18)
C2—C1—H1B	109.5	O1—C13—C12	128.9 (2)
H1A—C1—H1B	109.5	O2—C13—C12	116.2 (2)
C2—C1—H1C	109.5	O4—C14—O3	122.0 (2)
H1A—C1—H1C	109.5	O4—C14—C12	127.6 (2)
H1B—C1—H1C	109.5	O3—C14—C12	110.4 (2)
N1—C2—C1	114.2 (2)	C16—C15—C20	121.6 (2)
N1—C2—H2A	108.7	C16—C15—H15	119.2
C1—C2—H2A	108.7	C20—C15—H15	119.2
N1—C2—H2B	108.7	C17—C16—C15	119.31 (18)
C1—C2—H2B	108.7	C17—C16—H16	120.3
H2A—C2—H2B	107.6	C15—C16—H16	120.3
N1—C3—C4	113.6 (2)	C16—C17—C18	121.0 (2)
N1—C3—H3A	108.8	C16—C17—O3	121.06 (18)
C4—C3—H3A	108.8	C18—C17—O3	117.9 (2)
N1—C3—H3B	108.8	C19—C18—C17	119.2 (2)
C4—C3—H3B	108.8	C19—C18—H18	120.4
H3A—C3—H3B	107.7	C17—C18—H18	120.4
C3—C4—H4A	109.5	C18—C19—C20	121.68 (19)
C3—C4—H4B	109.5	C18—C19—H19	119.2
H4A—C4—H4B	109.5	C20—C19—H19	119.2
C3—C4—H4C	109.5	C19—C20—C15	117.2 (2)
H4A—C4—H4C	109.5	C19—C20—C21	121.35 (18)
H4B—C4—H4C	109.5	C15—C20—C21	121.4 (2)
O2—C5—C6	116.87 (18)	C26—C21—C22	117.3 (2)
O2—C5—C10	119.93 (19)	C26—C21—C20	121.94 (18)
C6—C5—C10	123.2 (2)	C22—C21—C20	120.8 (2)
C5—C6—C7	119.85 (19)	C23—C22—C21	121.2 (2)
C5—C6—H6	120.1	C23—C22—H22	119.4
C7—C6—H6	120.1	C21—C22—H22	119.4
N1—C7—C6	121.63 (19)	C22—C23—C24	120.7 (2)
N1—C7—C8	120.9 (2)	C22—C23—H23	119.6
C6—C7—C8	117.5 (2)	C24—C23—H23	119.6
C9—C8—C7	121.2 (2)	C23—C24—C25	119.3 (2)
C9—C8—H8	119.4	C23—C24—C27	119.77 (19)
C7—C8—H8	119.4	C25—C24—C27	120.9 (2)
C8—C9—C10	122.0 (2)	C26—C25—C24	119.4 (2)
C8—C9—H9	119.0	C26—C25—H25	120.3
C10—C9—H9	119.0	C24—C25—H25	120.3
C11—C10—C9	125.81 (19)	C25—C26—C21	122.1 (2)
C11—C10—C5	117.9 (2)	C25—C26—H26	119.0
C9—C10—C5	116.2 (2)	C21—C26—H26	119.0
C12—C11—C10	122.29 (19)	N2—C27—C24	177.5 (3)
C7—N1—C2—C1	78.6 (3)	C17—O3—C14—C12	178.42 (18)
C3—N1—C2—C1	−98.1 (2)	C11—C12—C14—O4	168.8 (3)
C7—N1—C3—C4	−87.7 (3)	C13—C12—C14—O4	−11.6 (4)
C2—N1—C3—C4	88.9 (3)	C11—C12—C14—O3	−11.4 (3)
C13—O2—C5—C6	178.28 (18)	C13—C12—C14—O3	168.26 (18)
C13—O2—C5—C10	−1.8 (3)	C20—C15—C16—C17	0.4 (4)
O2—C5—C6—C7	179.15 (18)	C15—C16—C17—C18	0.3 (4)
C10—C5—C6—C7	−0.8 (3)	C15—C16—C17—O3	−176.0 (2)
C2—N1—C7—C6	−177.0 (2)	C14—O3—C17—C16	−68.9 (3)
C3—N1—C7—C6	−0.5 (3)	C14—O3—C17—C18	114.7 (2)
C2—N1—C7—C8	3.6 (3)	C16—C17—C18—C19	−0.5 (4)
C3—N1—C7—C8	−179.86 (19)	O3—C17—C18—C19	176.0 (2)
C5—C6—C7—N1	−177.34 (19)	C17—C18—C19—C20	−0.1 (4)
C5—C6—C7—C8	2.1 (3)	C18—C19—C20—C15	0.7 (4)
N1—C7—C8—C9	177.9 (2)	C18—C19—C20—C21	−177.7 (2)
C6—C7—C8—C9	−1.6 (3)	C16—C15—C20—C19	−0.9 (4)
C7—C8—C9—C10	−0.3 (3)	C16—C15—C20—C21	177.6 (2)
C8—C9—C10—C11	−179.9 (2)	C19—C20—C21—C26	−159.0 (2)
C8—C9—C10—C5	1.6 (3)	C15—C20—C21—C26	22.6 (4)
O2—C5—C10—C11	0.3 (3)	C19—C20—C21—C22	22.7 (3)
C6—C5—C10—C11	−179.71 (19)	C15—C20—C21—C22	−155.6 (2)
O2—C5—C10—C9	179.01 (18)	C26—C21—C22—C23	−0.1 (3)
C6—C5—C10—C9	−1.0 (3)	C20—C21—C22—C23	178.2 (2)
C9—C10—C11—C12	−179.0 (2)	C21—C22—C23—C24	−0.8 (4)
C5—C10—C11—C12	−0.4 (3)	C22—C23—C24—C25	1.4 (4)
C10—C11—C12—C13	1.8 (3)	C22—C23—C24—C27	−178.6 (2)
C10—C11—C12—C14	−178.57 (19)	C23—C24—C25—C26	−1.0 (4)
C5—O2—C13—O1	−175.22 (18)	C27—C24—C25—C26	179.0 (2)
C5—O2—C13—C12	3.0 (3)	C24—C25—C26—C21	0.1 (4)
C11—C12—C13—O1	175.0 (2)	C22—C21—C26—C25	0.5 (4)
C14—C12—C13—O1	−4.7 (3)	C20—C21—C26—C25	−177.8 (2)
C11—C12—C13—O2	−3.0 (3)	C23—C24—C27—N2	8 (6)
C14—C12—C13—O2	177.36 (17)	C25—C24—C27—N2	−172 (6)
C17—O3—C14—O4	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.53	3.446 (3)	170
C11—H11···N2ii	0.93	2.59	3.435 (3)	152
C16—H16···O1iii	0.93	2.54	3.465 (3)	177
C1—H1B···Cg3iv	0.96	2.82	3.626 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.53	3.446 (3)	170
C11—H11⋯N2ii	0.93	2.59	3.435 (3)	152
C16—H16⋯O1iii	0.93	2.54	3.465 (3)	177
C1—H1B⋯Cg3iv	0.96	2.82	3.626 (3)	142

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