6,8-Di-tert-butyl-3-(4-nitro-phen-yl)-2H-chromen-2-one.

The title compound, C(23)H(25)NO(4), was synthesized by the reaction of 2-(4-nitro-phen-yl)acetonitrile and 3,5-di-tert-butyl-2-hydroxy-benzaldehyde. The dihedral angle formed by the benzene ring and the mean plane through the benzopyran-one ring system is 35.57 (5)°. The nitro group is almost coplanar with the attached benzene ring [dihedral angle = 5.19 (15)°]. The crystal packing is stabilized by an inter-molecular C-H⋯O hydrogen-bond inter-action.

Related literature

For the applications and biological activity of coumarin deriv­atives, see: Tian et al. (2000 ▶); Fun et al. (2009 ▶).

Experimental

Crystal data

C23H25NO4

M = 379.44

Orthorhombic,

a = 14.6463 (13) Å

b = 11.8634 (10) Å

c = 23.604 (2) Å

V = 4101.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.982, T max = 1.000

33748 measured reflections

4736 independent reflections

2809 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.140

S = 1.01

4736 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002321/rz2409sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002321/rz2409Isup2.hkl

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

C23H25NO4	F(000) = 1616
Mr = 379.44	Dx = 1.229 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5698 reflections
a = 14.6463 (13) Å	θ = 3.1–27.3°
b = 11.8634 (10) Å	µ = 0.08 mm−1
c = 23.604 (2) Å	T = 293 K
V = 4101.3 (6) Å3	Block, yellow
Z = 8	0.20 × 0.20 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	4736 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.2°
phi and ω scans	h = −19→18
Absorption correction: multi-scan (SADABS; Bruker,2000)	k = −15→15
Tmin = 0.982, Tmax = 1.000	l = −30→26
33748 measured reflections

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.7021P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4736 reflections	Δρmax = 0.19 e Å−3
254 parameters	Δρmin = −0.18 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: 0.0021 (4)

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
O1	0.14469 (8)	0.87691 (10)	0.19264 (5)	0.0519 (3)
C1	0.04378 (11)	0.96286 (14)	0.12603 (7)	0.0423 (4)
C2	0.05769 (11)	0.88906 (14)	0.17099 (7)	0.0425 (4)
N1	0.50655 (12)	1.22755 (18)	0.01632 (8)	0.0709 (5)
O2	0.49270 (12)	1.31945 (18)	−0.00487 (8)	0.1067 (6)
C3	−0.01328 (11)	0.82746 (14)	0.19572 (7)	0.0434 (4)
O3	0.58048 (12)	1.18104 (17)	0.01503 (9)	0.1104 (7)
C4	−0.09936 (11)	0.84849 (14)	0.17326 (7)	0.0459 (4)
H4A	−0.1486	0.8107	0.1893	0.055*
C5	−0.11757 (11)	0.92252 (14)	0.12817 (7)	0.0433 (4)
C6	−0.04451 (11)	0.97845 (14)	0.10493 (7)	0.0452 (4)
H6A	−0.0539	1.0274	0.0747	0.054*
C7	0.00116 (12)	0.74480 (15)	0.24487 (8)	0.0503 (4)
C8	0.07354 (17)	0.65680 (19)	0.22987 (11)	0.0861 (7)
H8A	0.1299	0.6940	0.2208	0.129*
H8B	0.0534	0.6137	0.1978	0.129*
H8C	0.0828	0.6075	0.2616	0.129*
C9	0.02893 (15)	0.8108 (2)	0.29770 (8)	0.0726 (6)
H9A	0.0843	0.8516	0.2902	0.109*
H9B	0.0386	0.7595	0.3286	0.109*
H9C	−0.0187	0.8630	0.3075	0.109*
C10	−0.08682 (14)	0.68095 (18)	0.25937 (9)	0.0715 (6)
H10A	−0.1062	0.6380	0.2271	0.107*
H10B	−0.1337	0.7338	0.2695	0.107*
H10C	−0.0757	0.6310	0.2906	0.107*
C11	−0.21566 (11)	0.94186 (15)	0.10840 (7)	0.0475 (4)
C12	−0.26345 (13)	0.82947 (18)	0.09799 (10)	0.0705 (6)
H12A	−0.2316	0.7886	0.0690	0.106*
H12B	−0.3252	0.8430	0.0861	0.106*
H12C	−0.2637	0.7862	0.1323	0.106*
C13	−0.26683 (13)	1.00688 (19)	0.15457 (9)	0.0664 (6)
H13A	−0.2371	1.0778	0.1611	0.100*
H13B	−0.2669	0.9637	0.1890	0.100*
H13C	−0.3286	1.0199	0.1426	0.100*
C14	−0.21945 (13)	1.0105 (2)	0.05374 (9)	0.0685 (6)
H14A	−0.1895	1.0816	0.0595	0.103*
H14B	−0.2820	1.0232	0.0434	0.103*
H14C	−0.1892	0.9699	0.0240	0.103*
C15	0.12116 (11)	1.02005 (14)	0.10272 (7)	0.0456 (4)
H15A	0.1123	1.0684	0.0722	0.055*
C16	0.20632 (11)	1.00669 (14)	0.12319 (7)	0.0447 (4)
C17	0.22005 (12)	0.93221 (17)	0.17162 (8)	0.0529 (5)
C18	0.28618 (11)	1.06494 (15)	0.09819 (7)	0.0461 (4)
C19	0.37009 (12)	1.01170 (16)	0.09219 (8)	0.0565 (5)
H19A	0.3776	0.9389	0.1060	0.068*
C20	0.44247 (12)	1.06487 (18)	0.06604 (8)	0.0608 (5)
H20A	0.4984	1.0286	0.0623	0.073*
C21	0.43052 (12)	1.17234 (16)	0.04563 (7)	0.0538 (5)
C22	0.34929 (13)	1.22816 (16)	0.05115 (8)	0.0578 (5)
H22A	0.3425	1.3011	0.0373	0.069*
C23	0.27740 (12)	1.17399 (16)	0.07773 (8)	0.0544 (5)
H23A	0.2221	1.2115	0.0820	0.065*
O4	0.29087 (9)	0.91451 (14)	0.19558 (6)	0.0807 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0473 (7)	0.0605 (8)	0.0480 (7)	0.0011 (6)	−0.0026 (5)	0.0141 (6)
C1	0.0472 (9)	0.0418 (9)	0.0380 (9)	0.0019 (7)	0.0015 (7)	0.0018 (7)
C2	0.0442 (9)	0.0442 (9)	0.0390 (9)	0.0035 (7)	−0.0014 (7)	0.0002 (7)
N1	0.0655 (11)	0.0793 (14)	0.0680 (12)	−0.0223 (10)	0.0043 (9)	0.0057 (10)
O2	0.0982 (13)	0.1086 (15)	0.1132 (15)	−0.0251 (11)	0.0095 (10)	0.0500 (12)
C3	0.0530 (10)	0.0385 (9)	0.0387 (9)	0.0006 (7)	0.0008 (7)	−0.0009 (7)
O3	0.0677 (10)	0.1078 (14)	0.1556 (18)	−0.0113 (10)	0.0351 (11)	0.0174 (13)
C4	0.0496 (9)	0.0436 (10)	0.0445 (10)	−0.0030 (7)	0.0030 (7)	0.0015 (8)
C5	0.0468 (9)	0.0425 (9)	0.0405 (9)	0.0014 (7)	−0.0001 (7)	−0.0029 (8)
C6	0.0501 (10)	0.0452 (10)	0.0402 (9)	0.0048 (8)	−0.0018 (7)	0.0055 (7)
C7	0.0563 (10)	0.0488 (10)	0.0458 (10)	−0.0016 (8)	−0.0010 (8)	0.0084 (8)
C8	0.1032 (18)	0.0653 (14)	0.0898 (17)	0.0275 (13)	0.0165 (14)	0.0257 (13)
C9	0.0846 (14)	0.0847 (16)	0.0485 (12)	−0.0168 (12)	−0.0113 (10)	0.0076 (11)
C10	0.0800 (14)	0.0669 (13)	0.0676 (14)	−0.0178 (11)	−0.0094 (11)	0.0259 (11)
C11	0.0448 (9)	0.0492 (10)	0.0486 (10)	0.0028 (8)	−0.0006 (7)	0.0013 (8)
C12	0.0577 (12)	0.0658 (14)	0.0879 (16)	−0.0063 (10)	−0.0137 (10)	−0.0057 (12)
C13	0.0577 (11)	0.0726 (14)	0.0691 (13)	0.0102 (10)	0.0083 (10)	−0.0038 (11)
C14	0.0527 (10)	0.0902 (16)	0.0627 (13)	0.0075 (10)	−0.0050 (9)	0.0145 (12)
C15	0.0504 (10)	0.0468 (10)	0.0396 (9)	0.0006 (8)	0.0013 (7)	0.0060 (8)
C16	0.0455 (9)	0.0467 (10)	0.0420 (9)	−0.0014 (7)	0.0005 (7)	0.0019 (8)
C17	0.0458 (9)	0.0635 (12)	0.0494 (10)	−0.0002 (9)	−0.0016 (8)	0.0092 (9)
C18	0.0481 (9)	0.0507 (10)	0.0394 (9)	−0.0027 (8)	−0.0034 (7)	−0.0001 (8)
C19	0.0533 (10)	0.0557 (12)	0.0604 (12)	0.0012 (9)	0.0013 (9)	0.0089 (9)
C20	0.0484 (10)	0.0694 (13)	0.0646 (13)	0.0002 (9)	0.0032 (9)	0.0039 (10)
C21	0.0540 (10)	0.0600 (12)	0.0473 (10)	−0.0146 (9)	0.0005 (8)	−0.0002 (9)
C22	0.0650 (12)	0.0484 (11)	0.0600 (12)	−0.0077 (9)	−0.0025 (9)	0.0054 (9)
C23	0.0519 (10)	0.0514 (11)	0.0600 (11)	0.0008 (8)	−0.0009 (8)	0.0013 (9)
O4	0.0516 (8)	0.1155 (13)	0.0749 (10)	−0.0047 (8)	−0.0127 (7)	0.0394 (9)

O1—C17	1.376 (2)	C11—C12	1.526 (3)
O1—C2	1.3804 (19)	C11—C14	1.527 (3)
C1—C2	1.391 (2)	C11—C13	1.531 (2)
C1—C6	1.398 (2)	C12—H12A	0.9600
C1—C15	1.431 (2)	C12—H12B	0.9600
C2—C3	1.398 (2)	C12—H12C	0.9600
N1—O3	1.216 (2)	C13—H13A	0.9600
N1—O2	1.216 (2)	C13—H13B	0.9600
N1—C21	1.466 (2)	C13—H13C	0.9600
C3—C4	1.390 (2)	C14—H14A	0.9600
C3—C7	1.534 (2)	C14—H14B	0.9600
C4—C5	1.405 (2)	C14—H14C	0.9600
C4—H4A	0.9300	C15—C16	1.347 (2)
C5—C6	1.373 (2)	C15—H15A	0.9300
C5—C11	1.528 (2)	C16—C17	1.459 (2)
C6—H6A	0.9300	C16—C18	1.481 (2)
C7—C9	1.528 (3)	C17—O4	1.200 (2)
C7—C8	1.529 (3)	C18—C23	1.387 (2)
C7—C10	1.533 (2)	C18—C19	1.389 (2)
C8—H8A	0.9600	C19—C20	1.379 (2)
C8—H8B	0.9600	C19—H19A	0.9300
C8—H8C	0.9600	C20—C21	1.374 (3)
C9—H9A	0.9600	C20—H20A	0.9300
C9—H9B	0.9600	C21—C22	1.368 (3)
C9—H9C	0.9600	C22—C23	1.384 (2)
C10—H10A	0.9600	C22—H22A	0.9300
C10—H10B	0.9600	C23—H23A	0.9300
C10—H10C	0.9600
C17—O1—C2	123.84 (13)	C12—C11—C5	110.45 (15)
C2—C1—C6	119.39 (15)	C14—C11—C5	111.87 (14)
C2—C1—C15	118.41 (15)	C13—C11—C5	108.56 (14)
C6—C1—C15	122.20 (15)	C11—C12—H12A	109.5
O1—C2—C1	118.92 (14)	C11—C12—H12B	109.5
O1—C2—C3	118.49 (14)	H12A—C12—H12B	109.5
C1—C2—C3	122.59 (15)	C11—C12—H12C	109.5
O3—N1—O2	123.03 (19)	H12A—C12—H12C	109.5
O3—N1—C21	119.1 (2)	H12B—C12—H12C	109.5
O2—N1—C21	117.90 (19)	C11—C13—H13A	109.5
C4—C3—C2	114.90 (15)	C11—C13—H13B	109.5
C4—C3—C7	121.89 (15)	H13A—C13—H13B	109.5
C2—C3—C7	123.20 (14)	C11—C13—H13C	109.5
C3—C4—C5	124.96 (15)	H13A—C13—H13C	109.5
C3—C4—H4A	117.5	H13B—C13—H13C	109.5
C5—C4—H4A	117.5	C11—C14—H14A	109.5
C6—C5—C4	117.16 (15)	C11—C14—H14B	109.5
C6—C5—C11	122.55 (15)	H14A—C14—H14B	109.5
C4—C5—C11	120.24 (14)	C11—C14—H14C	109.5
C5—C6—C1	120.96 (15)	H14A—C14—H14C	109.5
C5—C6—H6A	119.5	H14B—C14—H14C	109.5
C1—C6—H6A	119.5	C16—C15—C1	122.66 (16)
C9—C7—C3	109.04 (15)	C16—C15—H15A	118.7
C9—C7—C8	110.76 (17)	C1—C15—H15A	118.7
C3—C7—C8	110.91 (15)	C15—C16—C17	118.68 (15)
C9—C7—C10	107.15 (16)	C15—C16—C18	122.24 (15)
C3—C7—C10	111.65 (14)	C17—C16—C18	119.07 (14)
C8—C7—C10	107.27 (16)	O4—C17—O1	116.10 (16)
C7—C8—H8A	109.5	O4—C17—C16	126.47 (17)
C7—C8—H8B	109.5	O1—C17—C16	117.43 (14)
H8A—C8—H8B	109.5	C23—C18—C19	118.07 (16)
C7—C8—H8C	109.5	C23—C18—C16	120.05 (15)
H8A—C8—H8C	109.5	C19—C18—C16	121.82 (16)
H8B—C8—H8C	109.5	C18—C19—C20	121.18 (18)
C7—C9—H9A	109.5	C18—C19—H19A	119.4
C7—C9—H9B	109.5	C20—C19—H19A	119.4
H9A—C9—H9B	109.5	C21—C20—C19	118.90 (18)
C7—C9—H9C	109.5	C21—C20—H20A	120.5
H9A—C9—H9C	109.5	C19—C20—H20A	120.5
H9B—C9—H9C	109.5	C22—C21—C20	121.77 (17)
C7—C10—H10A	109.5	C22—C21—N1	119.31 (18)
C7—C10—H10B	109.5	C20—C21—N1	118.91 (18)
H10A—C10—H10B	109.5	C21—C22—C23	118.69 (18)
C7—C10—H10C	109.5	C21—C22—H22A	120.7
H10A—C10—H10C	109.5	C23—C22—H22A	120.7
H10B—C10—H10C	109.5	C18—C23—C22	121.37 (17)
C12—C11—C14	108.27 (16)	C18—C23—H23A	119.3
C12—C11—C13	109.29 (16)	C22—C23—H23A	119.3
C14—C11—C13	108.35 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2i	0.93	2.55	3.409 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2i	0.93	2.55	3.409 (3)	154

Symmetry code: (i) .