(E)-2-{Eth-yl[4-(4-nitro-phenyl-diazen-yl)phen-yl]amino}ethyl anthracene-9-carboxyl-ate.

The crystal structure of the title compound, C(31)H(26)N(4)O(4), displays a trans conformation for the nitro-phenyl-diazenyl portion of the mol-ecule. Packing diagrams indicate that weak C-H⋯O hydrogen bonds, likely associated with a strong dipole moment present in the mol-ecule, dictate the arrangement of mol-ecules in the crystal structure.

Related literature

Simmons et al. (2007 ▶) describe the use of the title compound in the fabrication of carbon nanotubes with optically modulated electronic conduction. Sekkat et al. (1992 ▶) document the use of Disperse Red 1 for reversible photoisomerization in thin films.

For related literature, see: Atassi et al. (1998 ▶); Becke (1993 ▶).

Experimental

Crystal data

C31H26N4O4

M = 518.56

Triclinic,

a = 9.3161 (9) Å

b = 10.6586 (10) Å

c = 13.5328 (13) Å

α = 101.134 (3)°

β = 104.667 (4)°

γ = 99.779 (3)°

V = 1241.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (2) K

0.20 × 0.08 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.982, T max = 0.994

9650 measured reflections

4824 independent reflections

2786 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.123

S = 1.02

4824 reflections

353 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: XSHELL (Bruker, 2000 ▶); molecular graphics: XSHELL and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004108/fl2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004108/fl2188Isup2.hkl

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

C31H26N4O4	Z = 2
Mr = 518.56	F000 = 544
Triclinic, P1	Dx = 1.388 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.3161 (9) Å	Cell parameters from 100 reflections
b = 10.6586 (10) Å	θ = 1.6–26.0º
c = 13.5328 (13) Å	µ = 0.09 mm−1
α = 101.134 (3)º	T = 173 (2) K
β = 104.667 (4)º	Irregular, orange
γ = 99.779 (3)º	0.20 × 0.08 × 0.06 mm
V = 1241.2 (2) Å3

Bruker SMART CCD area-detector diffractometer	4824 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.050
Detector resolution: 0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 1.6º
phi and ω scans	h = −11→11
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −13→13
Tmin = 0.982, Tmax = 0.994	l = −16→16
9650 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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0333P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4824 reflections	Δρmax = 0.21 e Å−3
353 parameters	Δρmin = −0.21 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 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
C1	0.4311 (4)	0.4301 (3)	1.1818 (2)	0.0357 (8)
H1	0.3552	0.3878	1.1167	0.043*
C2	0.3871 (4)	0.4647 (3)	1.2740 (2)	0.0380 (8)
H2	0.2823	0.4455	1.2705	0.046*
C3	0.5796 (3)	0.4565 (3)	1.1849 (2)	0.0314 (8)
H3	0.6066	0.4332	1.1218	0.038*
C4	0.4936 (3)	0.5249 (3)	1.3672 (2)	0.0330 (8)
H4	0.4624	0.5486	1.4285	0.040*
C5	0.6965 (3)	0.5190 (3)	1.2820 (2)	0.0256 (7)
C6	0.6513 (3)	0.5536 (3)	1.3752 (2)	0.0267 (7)
C7	0.8515 (3)	0.5491 (3)	1.2887 (2)	0.0233 (7)
C8	0.7638 (3)	0.6146 (3)	1.4708 (2)	0.0295 (8)
H8	0.7339	0.6371	1.5328	0.035*
C9	0.9635 (3)	0.6111 (3)	1.3845 (2)	0.0262 (7)
C10	0.9183 (3)	0.6438 (3)	1.4782 (2)	0.0271 (7)
C11	1.1225 (3)	0.6452 (3)	1.3946 (2)	0.0308 (8)
H11	1.1560	0.6250	1.3339	0.037*
C12	1.0315 (4)	0.7073 (3)	1.5759 (2)	0.0363 (8)
H12	1.0017	0.7292	1.6380	0.044*
C13	1.2262 (4)	0.7058 (3)	1.4892 (3)	0.0385 (9)
H13	1.3313	0.7279	1.4938	0.046*
C14	1.1804 (4)	0.7369 (3)	1.5816 (3)	0.0404 (9)
H14	1.2548	0.7785	1.6476	0.049*
C15	0.8955 (3)	0.5179 (3)	1.1890 (2)	0.0262 (7)
C16	0.9915 (3)	0.3710 (3)	1.0822 (2)	0.0283 (7)
H16A	1.0823	0.4372	1.0856	0.034*
H16B	0.9086	0.3672	1.0185	0.034*
C17	1.0292 (3)	0.2372 (3)	1.0778 (2)	0.0306 (8)
H17A	1.1023	0.2286	1.0364	0.037*
H17B	1.0808	0.2334	1.1503	0.037*
C18	0.8293 (4)	0.0686 (3)	1.1033 (2)	0.0326 (8)
H18A	0.9052	0.0919	1.1739	0.039*
H18B	0.8035	−0.0283	1.0777	0.039*
C19	0.6864 (4)	0.1132 (3)	1.1141 (2)	0.0384 (9)
H19A	0.7124	0.2081	1.1454	0.058*
H19B	0.6428	0.0670	1.1595	0.058*
H19C	0.6117	0.0934	1.0443	0.058*
C20	0.8434 (3)	0.0764 (3)	0.9246 (2)	0.0252 (7)
C21	0.9076 (3)	0.1361 (3)	0.8559 (2)	0.0271 (7)
H21	0.9850	0.2148	0.8846	0.032*
C22	0.8607 (3)	0.0830 (3)	0.7490 (2)	0.0274 (7)
H22	0.9083	0.1238	0.7053	0.033*
C23	0.7442 (3)	−0.0300 (3)	0.7038 (2)	0.0248 (7)
C24	0.6742 (3)	−0.0860 (3)	0.7695 (2)	0.0275 (7)
H24	0.5922	−0.1614	0.7394	0.033*
C25	0.7210 (3)	−0.0349 (3)	0.8769 (2)	0.0259 (7)
H25	0.6704	−0.0750	0.9195	0.031*
C26	0.6993 (3)	−0.0968 (3)	0.4302 (2)	0.0248 (7)
C27	0.7983 (3)	−0.1047 (3)	0.3689 (2)	0.0271 (7)
H27	0.9051	−0.0733	0.4009	0.033*
C28	0.7414 (3)	−0.1583 (3)	0.2614 (2)	0.0270 (7)
H28	0.8081	−0.1663	0.2190	0.032*
C29	0.5850 (3)	−0.1999 (3)	0.2170 (2)	0.0255 (7)
C30	0.4844 (3)	−0.1891 (3)	0.2755 (2)	0.0303 (8)
H30	0.3775	−0.2172	0.2427	0.036*
C31	0.5424 (3)	−0.1365 (3)	0.3829 (2)	0.0298 (7)
H31	0.4751	−0.1274	0.4246	0.036*
N1	0.8986 (3)	0.1256 (2)	1.03191 (18)	0.0281 (6)
N2	0.6851 (3)	−0.0883 (2)	0.59401 (18)	0.0278 (6)
N3	0.7671 (3)	−0.0435 (2)	0.54054 (18)	0.0281 (6)
N4	0.5237 (3)	−0.2560 (2)	0.10309 (19)	0.0333 (7)
O1	0.9436 (2)	0.40590 (19)	1.17640 (14)	0.0297 (5)
O2	0.8885 (3)	0.5849 (2)	1.12621 (17)	0.0432 (6)
O3	0.6111 (3)	−0.2485 (2)	0.04881 (16)	0.0490 (7)
O4	0.3869 (3)	−0.3075 (2)	0.06570 (16)	0.0461 (6)

	U11	U22	U33	U12	U13	U23
C1	0.030 (2)	0.0329 (19)	0.036 (2)	0.0005 (16)	0.0081 (16)	−0.0016 (16)
C2	0.030 (2)	0.035 (2)	0.046 (2)	0.0021 (16)	0.0162 (17)	0.0015 (17)
C3	0.036 (2)	0.0261 (18)	0.0289 (18)	0.0055 (15)	0.0106 (16)	−0.0005 (14)
C4	0.036 (2)	0.0326 (19)	0.035 (2)	0.0098 (16)	0.0191 (17)	0.0063 (16)
C5	0.0308 (19)	0.0178 (16)	0.0267 (18)	0.0049 (14)	0.0099 (15)	0.0010 (13)
C6	0.0305 (19)	0.0233 (17)	0.0282 (18)	0.0062 (14)	0.0133 (15)	0.0046 (14)
C7	0.0281 (18)	0.0186 (16)	0.0264 (17)	0.0059 (13)	0.0135 (14)	0.0054 (13)
C8	0.040 (2)	0.0282 (18)	0.0238 (17)	0.0098 (15)	0.0150 (16)	0.0049 (14)
C9	0.0315 (19)	0.0203 (16)	0.0285 (18)	0.0071 (14)	0.0084 (15)	0.0096 (14)
C10	0.0320 (19)	0.0227 (17)	0.0256 (18)	0.0058 (14)	0.0084 (15)	0.0045 (14)
C11	0.0299 (19)	0.0324 (19)	0.0326 (19)	0.0089 (15)	0.0110 (16)	0.0100 (15)
C12	0.043 (2)	0.036 (2)	0.0251 (18)	0.0072 (17)	0.0068 (16)	0.0028 (15)
C13	0.029 (2)	0.036 (2)	0.047 (2)	0.0041 (16)	0.0076 (17)	0.0102 (17)
C14	0.044 (2)	0.035 (2)	0.032 (2)	0.0020 (17)	0.0012 (17)	0.0036 (16)
C15	0.0232 (18)	0.0212 (17)	0.0312 (19)	0.0026 (14)	0.0074 (15)	0.0027 (14)
C16	0.0292 (18)	0.0356 (19)	0.0184 (16)	0.0067 (15)	0.0081 (14)	0.0021 (14)
C17	0.0261 (18)	0.0376 (19)	0.0230 (17)	0.0103 (15)	0.0047 (14)	−0.0035 (15)
C18	0.043 (2)	0.0314 (19)	0.0253 (18)	0.0130 (16)	0.0100 (16)	0.0077 (15)
C19	0.046 (2)	0.035 (2)	0.036 (2)	0.0086 (17)	0.0176 (17)	0.0064 (16)
C20	0.0260 (18)	0.0265 (18)	0.0263 (18)	0.0137 (14)	0.0094 (15)	0.0052 (14)
C21	0.0234 (17)	0.0249 (17)	0.0292 (18)	0.0042 (14)	0.0072 (14)	0.0000 (14)
C22	0.0256 (18)	0.0321 (18)	0.0276 (18)	0.0088 (15)	0.0114 (14)	0.0076 (15)
C23	0.0248 (17)	0.0263 (17)	0.0204 (17)	0.0071 (14)	0.0052 (14)	0.0003 (13)
C24	0.0282 (18)	0.0263 (17)	0.0242 (17)	0.0053 (14)	0.0061 (14)	0.0007 (14)
C25	0.0292 (18)	0.0249 (17)	0.0242 (17)	0.0075 (14)	0.0095 (14)	0.0046 (14)
C26	0.0329 (19)	0.0179 (16)	0.0247 (17)	0.0092 (14)	0.0085 (15)	0.0048 (13)
C27	0.0248 (17)	0.0273 (17)	0.0256 (18)	0.0035 (14)	0.0053 (14)	0.0033 (14)
C28	0.0268 (18)	0.0322 (18)	0.0250 (18)	0.0079 (15)	0.0095 (14)	0.0104 (14)
C29	0.0332 (19)	0.0233 (17)	0.0178 (16)	0.0077 (14)	0.0045 (14)	0.0032 (13)
C30	0.0271 (18)	0.0328 (19)	0.0285 (18)	0.0077 (15)	0.0050 (15)	0.0056 (15)
C31	0.0293 (19)	0.0346 (19)	0.0268 (18)	0.0101 (15)	0.0096 (15)	0.0070 (15)
N1	0.0309 (16)	0.0331 (15)	0.0189 (14)	0.0075 (12)	0.0072 (12)	0.0028 (12)
N2	0.0308 (15)	0.0296 (15)	0.0245 (15)	0.0111 (12)	0.0093 (12)	0.0049 (12)
N3	0.0306 (16)	0.0308 (15)	0.0218 (14)	0.0083 (12)	0.0070 (12)	0.0037 (12)
N4	0.0376 (18)	0.0333 (16)	0.0253 (16)	0.0071 (14)	0.0045 (14)	0.0064 (13)
O1	0.0383 (13)	0.0302 (12)	0.0231 (12)	0.0128 (10)	0.0121 (10)	0.0043 (10)
O2	0.0657 (17)	0.0346 (14)	0.0456 (15)	0.0187 (12)	0.0329 (13)	0.0194 (12)
O3	0.0528 (16)	0.0625 (17)	0.0281 (13)	0.0052 (13)	0.0163 (12)	0.0045 (12)
O4	0.0316 (14)	0.0597 (16)	0.0327 (14)	0.0039 (12)	−0.0035 (11)	0.0011 (12)

C1—C3	1.352 (4)	C18—N1	1.460 (3)
C1—C2	1.411 (4)	C18—C19	1.519 (4)
C1—H1	0.9500	C18—H18A	0.9900
C2—C4	1.350 (4)	C18—H18B	0.9900
C2—H2	0.9500	C19—H19A	0.9800
C3—C5	1.431 (4)	C19—H19B	0.9800
C3—H3	0.9500	C19—H19C	0.9800
C4—C6	1.421 (4)	C20—N1	1.373 (3)
C4—H4	0.9500	C20—C25	1.413 (4)
C5—C7	1.400 (4)	C20—C21	1.416 (4)
C5—C6	1.431 (4)	C21—C22	1.373 (4)
C6—C8	1.397 (4)	C21—H21	0.9500
C7—C9	1.399 (4)	C22—C23	1.392 (4)
C7—C15	1.500 (4)	C22—H22	0.9500
C8—C10	1.394 (4)	C23—C24	1.392 (4)
C8—H8	0.9500	C23—N2	1.418 (3)
C9—C11	1.429 (4)	C24—C25	1.376 (4)
C9—C10	1.433 (4)	C24—H24	0.9500
C10—C12	1.422 (4)	C25—H25	0.9500
C11—C13	1.354 (4)	C26—C27	1.391 (4)
C11—H11	0.9500	C26—C31	1.391 (4)
C12—C14	1.349 (4)	C26—N3	1.423 (3)
C12—H12	0.9500	C27—C28	1.381 (4)
C13—C14	1.418 (4)	C27—H27	0.9500
C13—H13	0.9500	C28—C29	1.384 (4)
C14—H14	0.9500	C28—H28	0.9500
C15—O2	1.207 (3)	C29—C30	1.378 (4)
C15—O1	1.341 (3)	C29—N4	1.463 (3)
C16—O1	1.457 (3)	C30—C31	1.379 (4)
C16—C17	1.519 (4)	C30—H30	0.9500
C16—H16A	0.9900	C31—H31	0.9500
C16—H16B	0.9900	N2—N3	1.275 (3)
C17—N1	1.457 (3)	N4—O4	1.229 (3)
C17—H17A	0.9900	N4—O3	1.230 (3)
C17—H17B	0.9900
C3—C1—C2	120.9 (3)	N1—C18—C19	114.1 (3)
C3—C1—H1	119.5	N1—C18—H18A	108.7
C2—C1—H1	119.5	C19—C18—H18A	108.7
C4—C2—C1	120.2 (3)	N1—C18—H18B	108.7
C4—C2—H2	119.9	C19—C18—H18B	108.7
C1—C2—H2	119.9	H18A—C18—H18B	107.6
C1—C3—C5	120.9 (3)	C18—C19—H19A	109.5
C1—C3—H3	119.6	C18—C19—H19B	109.5
C5—C3—H3	119.6	H19A—C19—H19B	109.5
C2—C4—C6	121.2 (3)	C18—C19—H19C	109.5
C2—C4—H4	119.4	H19A—C19—H19C	109.5
C6—C4—H4	119.4	H19B—C19—H19C	109.5
C7—C5—C6	119.2 (3)	N1—C20—C25	122.4 (3)
C7—C5—C3	122.8 (3)	N1—C20—C21	121.0 (3)
C6—C5—C3	118.0 (3)	C25—C20—C21	116.6 (3)
C8—C6—C4	122.4 (3)	C22—C21—C20	121.7 (3)
C8—C6—C5	118.9 (3)	C22—C21—H21	119.2
C4—C6—C5	118.8 (3)	C20—C21—H21	119.2
C9—C7—C5	121.6 (3)	C21—C22—C23	120.8 (3)
C9—C7—C15	120.1 (3)	C21—C22—H22	119.6
C5—C7—C15	118.2 (3)	C23—C22—H22	119.6
C10—C8—C6	122.2 (3)	C22—C23—C24	118.4 (3)
C10—C8—H8	118.9	C22—C23—N2	124.4 (3)
C6—C8—H8	118.9	C24—C23—N2	117.1 (3)
C7—C9—C11	123.4 (3)	C25—C24—C23	121.6 (3)
C7—C9—C10	119.1 (3)	C25—C24—H24	119.2
C11—C9—C10	117.5 (3)	C23—C24—H24	119.2
C8—C10—C12	121.6 (3)	C24—C25—C20	120.8 (3)
C8—C10—C9	118.9 (3)	C24—C25—H25	119.6
C12—C10—C9	119.5 (3)	C20—C25—H25	119.6
C13—C11—C9	121.1 (3)	C27—C26—C31	120.1 (3)
C13—C11—H11	119.5	C27—C26—N3	116.6 (3)
C9—C11—H11	119.5	C31—C26—N3	123.3 (3)
C14—C12—C10	121.0 (3)	C28—C27—C26	120.0 (3)
C14—C12—H12	119.5	C28—C27—H27	120.0
C10—C12—H12	119.5	C26—C27—H27	120.0
C11—C13—C14	121.0 (3)	C27—C28—C29	118.5 (3)
C11—C13—H13	119.5	C27—C28—H28	120.8
C14—C13—H13	119.5	C29—C28—H28	120.8
C12—C14—C13	120.0 (3)	C30—C29—C28	122.6 (3)
C12—C14—H14	120.0	C30—C29—N4	118.6 (3)
C13—C14—H14	120.0	C28—C29—N4	118.8 (3)
O2—C15—O1	123.0 (3)	C29—C30—C31	118.5 (3)
O2—C15—C7	124.5 (3)	C29—C30—H30	120.8
O1—C15—C7	112.4 (3)	C31—C30—H30	120.8
O1—C16—C17	107.3 (2)	C30—C31—C26	120.3 (3)
O1—C16—H16A	110.3	C30—C31—H31	119.9
C17—C16—H16A	110.3	C26—C31—H31	119.9
O1—C16—H16B	110.3	C20—N1—C17	120.5 (2)
C17—C16—H16B	110.3	C20—N1—C18	121.5 (2)
H16A—C16—H16B	108.5	C17—N1—C18	118.0 (2)
N1—C17—C16	115.0 (2)	N3—N2—C23	113.5 (2)
N1—C17—H17A	108.5	N2—N3—C26	112.1 (2)
C16—C17—H17A	108.5	O4—N4—O3	122.8 (3)
N1—C17—H17B	108.5	O4—N4—C29	118.6 (3)
C16—C17—H17B	108.5	O3—N4—C29	118.6 (3)
H17A—C17—H17B	107.5	C15—O1—C16	115.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O3i	0.95	2.56	3.230 (4)	128
C3—H3···O4i	0.95	2.65	3.570 (4)	163
C16—H16B···O4i	0.99	2.61	3.462 (4)	144
C21—H21···O2ii	0.95	2.31	3.176 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O3i	0.95	2.56	3.230 (4)	128
C3—H3⋯O4i	0.95	2.65	3.570 (4)	163
C16—H16B⋯O4i	0.99	2.61	3.462 (4)	144
C21—H21⋯O2ii	0.95	2.31	3.176 (4)	152

Symmetry codes: (i) ; (ii) .