(E)-4-[(4-Nitro-phen-yl)diazen-yl]phenyl anthracene-9-carboxyl-ate.

In the title compound, C(27)H(17)N(3)O(4), the azo group displays a trans conformation and the dihedral angles between the central benzene ring and the pendant anthracene and nitro-benzene rings are 82.94 (7) and 7.30 (9)°, respectively. In the crystal structure, weak C-H⋯O hydrogen bonds, likely associated with a dipole moment present on the mol-ecule, help to consolidate the packing.

Related literature

This structure is similar to the perviously reported compound (E)-2-{Eth­yl[4-(4-nitro­phenyl­diazen­yl)phen­yl]amino}ethyl anthracene-9-carboxyl­ate (Rodriguez, et al., 2008 ▶). For general background, see: Atassi et al. (1998 ▶); Becke (1993 ▶).

Experimental

Crystal data

C27H17N3O4

M = 447.44

Monoclinic,

a = 13.525 (2) Å

b = 8.6011 (14) Å

c = 18.956 (3) Å

β = 109.322 (3)°

V = 2080.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 (2) K

0.20 × 0.18 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.980, T max = 0.995

14511 measured reflections

3665 independent reflections

2752 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.03

3665 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XSHELL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034958/hb2827sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034958/hb2827Isup2.hkl

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

C27H17N3O4	F000 = 928
Mr = 447.44	Dx = 1.428 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 100 reflections
a = 13.525 (2) Å	θ = 1.6–25.0º
b = 8.6011 (14) Å	µ = 0.10 mm−1
c = 18.956 (3) Å	T = 173 (2) K
β = 109.322 (3)º	Plate, red
V = 2080.9 (6) Å3	0.20 × 0.18 × 0.05 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3665 independent reflections
Radiation source: fine-focus sealed tube	2752 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 0 pixels mm-1	θmax = 25.0º
T = 173(2) K	θmin = 1.6º
φ and ω scans	h = −16→16
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −10→10
Tmin = 0.980, Tmax = 0.995	l = −21→22
14511 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.7361P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3665 reflections	Δρmax = 0.39 e Å−3
307 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s, except the e.s.d. in the dihedral angle between two least-square (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	0.69229 (14)	1.52655 (19)	0.65761 (9)	0.0352 (4)
N2	0.44775 (13)	1.12430 (19)	0.43308 (9)	0.0350 (4)
N3	0.48826 (13)	1.08369 (18)	0.38663 (9)	0.0333 (4)
O1	0.78660 (13)	1.5368 (2)	0.66951 (9)	0.0581 (5)
O2	0.64573 (13)	1.60250 (18)	0.69126 (8)	0.0486 (4)
O3	0.26778 (10)	0.69438 (15)	0.15211 (7)	0.0304 (3)
O4	0.10043 (11)	0.77469 (17)	0.12517 (8)	0.0416 (4)
C1	0.63159 (15)	1.4180 (2)	0.59981 (10)	0.0272 (4)
C2	0.52768 (15)	1.3952 (2)	0.59086 (11)	0.0322 (5)
H2	0.4957	1.4476	0.6218	0.039*
C3	0.47087 (16)	1.2945 (2)	0.53590 (11)	0.0334 (5)
H3	0.3993	1.2749	0.5295	0.040*
C4	0.51755 (15)	1.2218 (2)	0.49006 (10)	0.0289 (5)
C5	0.62352 (16)	1.2433 (2)	0.50109 (11)	0.0307 (5)
H5	0.6556	1.1907	0.4703	0.037*
C6	0.68173 (16)	1.3411 (2)	0.55702 (11)	0.0304 (5)
H6	0.7545	1.3555	0.5660	0.037*
C7	0.42162 (15)	0.9862 (2)	0.32817 (10)	0.0298 (5)
C8	0.31857 (16)	0.9475 (2)	0.31890 (11)	0.0326 (5)
H8	0.2860	0.9874	0.3524	0.039*
C9	0.26266 (16)	0.8502 (2)	0.26061 (11)	0.0316 (5)
H9	0.1924	0.8218	0.2543	0.038*
C10	0.31210 (15)	0.7960 (2)	0.21211 (10)	0.0273 (4)
C11	0.41510 (15)	0.8342 (2)	0.22141 (11)	0.0296 (5)
H11	0.4480	0.7949	0.1879	0.036*
C12	0.46943 (16)	0.9293 (2)	0.27953 (11)	0.0318 (5)
H12	0.5401	0.9560	0.2862	0.038*
C13	0.16358 (15)	0.6938 (2)	0.11132 (11)	0.0281 (4)
C14	0.14418 (14)	0.5854 (2)	0.04656 (10)	0.0258 (4)
C15	0.09289 (14)	0.6443 (2)	−0.02570 (11)	0.0265 (4)
C16	0.05487 (14)	0.8006 (2)	−0.04087 (12)	0.0313 (5)
H16	0.0626	0.8699	−0.0004	0.038*
C17	0.00814 (16)	0.8515 (2)	−0.11171 (12)	0.0383 (5)
H17	−0.0159	0.9559	−0.1201	0.046*
C18	−0.00531 (17)	0.7513 (3)	−0.17329 (12)	0.0426 (6)
H18	−0.0391	0.7882	−0.2227	0.051*
C19	0.02967 (16)	0.6035 (2)	−0.16205 (12)	0.0381 (5)
H19	0.0206	0.5375	−0.2039	0.046*
C20	0.07981 (14)	0.5446 (2)	−0.08895 (11)	0.0287 (5)
C21	0.11527 (14)	0.3921 (2)	−0.07705 (11)	0.0296 (5)
H21	0.1070	0.3269	−0.1191	0.036*
C22	0.16242 (14)	0.3316 (2)	−0.00585 (11)	0.0256 (4)
C23	0.19358 (15)	0.1725 (2)	0.00493 (12)	0.0309 (5)
H23	0.1821	0.1069	−0.0373	0.037*
C24	0.23912 (15)	0.1134 (2)	0.07422 (12)	0.0345 (5)
H24	0.2597	0.0073	0.0803	0.041*
C25	0.25608 (15)	0.2095 (2)	0.13743 (12)	0.0339 (5)
H25	0.2886	0.1677	0.1860	0.041*
C26	0.22641 (15)	0.3615 (2)	0.12975 (11)	0.0312 (5)
H26	0.2376	0.4236	0.1732	0.037*
C27	0.17899 (14)	0.4293 (2)	0.05797 (11)	0.0260 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0431 (11)	0.0312 (10)	0.0275 (10)	−0.0035 (8)	0.0066 (8)	−0.0032 (8)
N2	0.0409 (10)	0.0305 (10)	0.0359 (10)	0.0027 (8)	0.0158 (9)	0.0012 (8)
N3	0.0388 (10)	0.0277 (9)	0.0353 (10)	0.0021 (8)	0.0148 (9)	0.0029 (8)
O1	0.0400 (10)	0.0717 (12)	0.0571 (11)	−0.0170 (9)	0.0088 (8)	−0.0273 (9)
O2	0.0602 (11)	0.0453 (9)	0.0393 (9)	0.0034 (8)	0.0155 (8)	−0.0165 (8)
O3	0.0253 (7)	0.0304 (8)	0.0328 (8)	−0.0026 (6)	0.0060 (6)	−0.0102 (6)
O4	0.0307 (8)	0.0404 (9)	0.0486 (9)	0.0042 (7)	0.0062 (7)	−0.0176 (7)
C1	0.0340 (11)	0.0229 (10)	0.0210 (10)	−0.0012 (8)	0.0040 (9)	0.0008 (8)
C2	0.0352 (12)	0.0302 (11)	0.0306 (11)	0.0052 (9)	0.0102 (9)	−0.0003 (9)
C3	0.0295 (11)	0.0335 (11)	0.0348 (12)	−0.0004 (9)	0.0074 (9)	0.0016 (9)
C4	0.0348 (12)	0.0224 (10)	0.0241 (10)	−0.0027 (9)	0.0023 (9)	0.0017 (8)
C5	0.0401 (12)	0.0276 (11)	0.0263 (11)	0.0024 (9)	0.0135 (9)	−0.0016 (9)
C6	0.0308 (11)	0.0299 (11)	0.0309 (11)	−0.0023 (9)	0.0106 (9)	0.0009 (9)
C7	0.0351 (12)	0.0226 (10)	0.0253 (11)	−0.0047 (9)	0.0013 (9)	0.0003 (8)
C8	0.0467 (13)	0.0280 (11)	0.0246 (11)	0.0042 (9)	0.0137 (10)	0.0006 (9)
C9	0.0327 (12)	0.0317 (11)	0.0296 (11)	−0.0027 (9)	0.0094 (9)	−0.0003 (9)
C10	0.0343 (11)	0.0202 (10)	0.0236 (10)	−0.0005 (8)	0.0045 (9)	−0.0015 (8)
C11	0.0316 (11)	0.0270 (10)	0.0282 (11)	−0.0010 (9)	0.0071 (9)	−0.0018 (9)
C12	0.0314 (11)	0.0301 (11)	0.0303 (11)	−0.0035 (9)	0.0056 (9)	−0.0022 (9)
C13	0.0271 (11)	0.0222 (10)	0.0337 (11)	−0.0021 (8)	0.0083 (9)	−0.0007 (9)
C14	0.0212 (10)	0.0246 (10)	0.0304 (11)	−0.0045 (8)	0.0069 (8)	−0.0032 (8)
C15	0.0202 (10)	0.0244 (10)	0.0343 (11)	−0.0031 (8)	0.0083 (9)	−0.0007 (9)
C16	0.0266 (11)	0.0249 (10)	0.0408 (13)	−0.0026 (8)	0.0091 (9)	−0.0020 (9)
C17	0.0350 (12)	0.0281 (11)	0.0482 (14)	0.0031 (9)	0.0092 (11)	0.0068 (10)
C18	0.0461 (14)	0.0416 (13)	0.0358 (13)	0.0042 (11)	0.0076 (11)	0.0094 (10)
C19	0.0422 (13)	0.0392 (13)	0.0316 (12)	0.0006 (10)	0.0105 (10)	−0.0004 (10)
C20	0.0256 (10)	0.0289 (11)	0.0318 (11)	−0.0015 (8)	0.0097 (9)	−0.0010 (9)
C21	0.0295 (11)	0.0299 (11)	0.0301 (11)	−0.0036 (9)	0.0108 (9)	−0.0062 (9)
C22	0.0213 (10)	0.0237 (10)	0.0319 (11)	−0.0034 (8)	0.0091 (9)	−0.0039 (8)
C23	0.0319 (11)	0.0251 (10)	0.0378 (12)	−0.0008 (9)	0.0142 (10)	−0.0050 (9)
C24	0.0336 (12)	0.0227 (10)	0.0466 (14)	−0.0001 (9)	0.0123 (10)	0.0022 (10)
C25	0.0313 (11)	0.0308 (11)	0.0353 (12)	−0.0014 (9)	0.0053 (9)	0.0056 (9)
C26	0.0319 (11)	0.0280 (11)	0.0314 (12)	−0.0040 (9)	0.0071 (9)	−0.0009 (9)
C27	0.0209 (10)	0.0248 (10)	0.0316 (11)	−0.0044 (8)	0.0078 (8)	−0.0019 (8)

N1—O1	1.223 (2)	C12—H12	0.9500
N1—O2	1.223 (2)	C13—C14	1.494 (3)
N1—C1	1.467 (2)	C14—C15	1.409 (3)
N2—N3	1.231 (2)	C14—C27	1.416 (3)
N2—C4	1.445 (2)	C15—C16	1.434 (3)
N3—C7	1.443 (2)	C15—C20	1.437 (3)
O3—C13	1.365 (2)	C16—C17	1.354 (3)
O3—C10	1.402 (2)	C16—H16	0.9500
O4—C13	1.196 (2)	C17—C18	1.413 (3)
C1—C2	1.373 (3)	C17—H17	0.9500
C1—C6	1.385 (3)	C18—C19	1.349 (3)
C2—C3	1.377 (3)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.420 (3)
C3—C4	1.381 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.389 (3)
C4—C5	1.391 (3)	C21—C22	1.389 (3)
C5—C6	1.378 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.426 (3)
C6—H6	0.9500	C22—C27	1.429 (3)
C7—C12	1.379 (3)	C23—C24	1.352 (3)
C7—C8	1.387 (3)	C23—H23	0.9500
C8—C9	1.393 (3)	C24—C25	1.411 (3)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.384 (3)	C25—C26	1.361 (3)
C9—H9	0.9500	C25—H25	0.9500
C10—C11	1.385 (3)	C26—C27	1.423 (3)
C11—C12	1.374 (3)	C26—H26	0.9500
C11—H11	0.9500
O1—N1—O2	123.42 (18)	O3—C13—C14	109.61 (15)
O1—N1—C1	118.41 (17)	C15—C14—C27	121.42 (17)
O2—N1—C1	118.17 (18)	C15—C14—C13	118.08 (16)
N3—N2—C4	111.35 (17)	C27—C14—C13	120.48 (17)
N2—N3—C7	113.66 (17)	C14—C15—C16	124.09 (18)
C13—O3—C10	123.10 (14)	C14—C15—C20	118.80 (17)
C2—C1—C6	122.62 (18)	C16—C15—C20	117.09 (17)
C2—C1—N1	118.71 (17)	C17—C16—C15	121.37 (19)
C6—C1—N1	118.67 (17)	C17—C16—H16	119.3
C1—C2—C3	118.39 (19)	C15—C16—H16	119.3
C1—C2—H2	120.8	C16—C17—C18	120.84 (19)
C3—C2—H2	120.8	C16—C17—H17	119.6
C2—C3—C4	120.25 (19)	C18—C17—H17	119.6
C2—C3—H3	119.9	C19—C18—C17	120.1 (2)
C4—C3—H3	119.9	C19—C18—H18	119.9
C3—C4—C5	120.56 (18)	C17—C18—H18	119.9
C3—C4—N2	114.30 (17)	C18—C19—C20	121.3 (2)
C5—C4—N2	125.14 (18)	C18—C19—H19	119.3
C6—C5—C4	119.65 (18)	C20—C19—H19	119.3
C6—C5—H5	120.2	C21—C20—C19	121.55 (18)
C4—C5—H5	120.2	C21—C20—C15	119.19 (18)
C5—C6—C1	118.43 (18)	C19—C20—C15	119.26 (18)
C5—C6—H6	120.8	C22—C21—C20	122.30 (18)
C1—C6—H6	120.8	C22—C21—H21	118.8
C12—C7—C8	120.27 (18)	C20—C21—H21	118.8
C12—C7—N3	114.06 (17)	C21—C22—C23	121.17 (17)
C8—C7—N3	125.67 (18)	C21—C22—C27	119.68 (17)
C7—C8—C9	120.27 (18)	C23—C22—C27	119.15 (18)
C7—C8—H8	119.9	C24—C23—C22	121.19 (19)
C9—C8—H8	119.9	C24—C23—H23	119.4
C10—C9—C8	118.32 (19)	C22—C23—H23	119.4
C10—C9—H9	120.8	C23—C24—C25	119.90 (19)
C8—C9—H9	120.8	C23—C24—H24	120.0
C9—C10—C11	121.49 (18)	C25—C24—H24	120.0
C9—C10—O3	125.30 (17)	C26—C25—C24	120.85 (19)
C11—C10—O3	113.16 (16)	C26—C25—H25	119.6
C12—C11—C10	119.47 (18)	C24—C25—H25	119.6
C12—C11—H11	120.3	C25—C26—C27	121.29 (19)
C10—C11—H11	120.3	C25—C26—H26	119.4
C11—C12—C7	120.18 (19)	C27—C26—H26	119.4
C11—C12—H12	119.9	C14—C27—C26	123.82 (17)
C7—C12—H12	119.9	C14—C27—C22	118.54 (17)
O4—C13—O3	123.49 (17)	C26—C27—C22	117.60 (17)
O4—C13—C14	126.81 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O2i	0.95	2.54	3.273 (3)	134
C17—H17···O4ii	0.95	2.57	3.509 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O2i	0.95	2.54	3.273 (3)	134
C17—H17⋯O4ii	0.95	2.57	3.509 (3)	169

Symmetry codes: (i) ; (ii) .