Literature DB >> 21581945

4-[4-(4-Nitro-phenyl-diazen-yl)phen-yl]hexa-nenitrile.

Ran-Zhe Lu¹, Lu-Na Han, Min Zhang, Bin Wang, Hai-Bo Wang.

Abstract

In the mol-ecule of the title compound, C(18)H(18)N(4)O(2), the aromatic rings are oriented at a dihedral angle of 3.72 (3)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. There are also C-H⋯π inter-actions.

Entities: CellLine Chemical Disease Gene

Year: 2009 PMID： 21581945 PMCID： PMC2968211 DOI： 10.1107/S1600536809000853

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background, see: Bach et al. (1996 ▶); Clark & Hester (1991 ▶); Taniike et al. (1996 ▶). For a related structure, see: Zhao et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H18N4O2 M = 322.36 Monoclinic, a = 20.113 (4) Å b = 10.590 (2) Å c = 7.6820 (15) Å β = 94.78 (3)° V = 1630.5 (6) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 (2) K 0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.964, T max = 0.991 3037 measured reflections 2951 independent reflections 1336 reflections with I > 2σ(I) R int = 0.061 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.072 wR(F 2) = 0.185 S = 0.98 2951 reflections 199 parameters 62 restraints H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.37 e Å−3 Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks D, I. DOI: 10.1107/S1600536809000853/hk2611sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000853/hk2611Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₈N₄O₂	F(000) = 680
M_r = 322.36	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 20.113 (4) Å	θ = 9–13°
b = 10.590 (2) Å	µ = 0.09 mm⁻¹
c = 7.6820 (15) Å	T = 293 K
β = 94.78 (3)°	Block, red
V = 1630.5 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.061
graphite	θ_max = 25.3°, θ_min = 1.0°
ω/2θ scans	h = 0→24
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.964, T_max = 0.991	l = −9→9
3037 measured reflections	3 standard reflections every 200 reflections
2951 independent reflections	intensity decay: 1%

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.060P)² + 1.P] where P = (F_o² + 2F_c²)/3
2951 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.32 e Å⁻³
62 restraints	Δρ_min = −0.37 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
N1	0.4653 (3)	−0.1899 (5)	0.4255 (7)	0.1057 (17)
C1	0.4327 (3)	−0.1281 (7)	0.4966 (8)	0.107 (2)
O1	−0.27421 (18)	0.0779 (4)	0.7659 (5)	0.0975 (13)
O2	−0.25317 (17)	0.2141 (3)	0.9614 (5)	0.0828 (11)
N2	0.07709 (17)	0.1393 (3)	0.8661 (4)	0.0479 (7)
N3	0.03734 (18)	0.0691 (3)	0.7775 (4)	0.0506 (9)
N4	−0.2356 (2)	0.1355 (4)	0.8566 (6)	0.0658 (11)
C2	0.3903 (2)	−0.0199 (5)	0.5602 (7)	0.0829 (10)
H2B	0.4142	0.0597	0.5607	0.099*
H2C	0.3493	−0.0113	0.4853	0.099*
C3	0.3747 (2)	−0.0512 (5)	0.7350 (7)	0.0829 (10)
H3B	0.4143	−0.0822	0.8022	0.099*
H3C	0.3411	−0.1171	0.7309	0.099*
C4	0.4104 (3)	0.0772 (6)	1.1039 (8)	0.105 (2)
H4A	0.4447	0.1228	1.1719	0.157*
H4B	0.4239	−0.0091	1.0920	0.157*
H4C	0.3698	0.0801	1.1613	0.157*
C5	0.3989 (2)	0.1368 (5)	0.9246 (7)	0.0808 (17)
H5A	0.3851	0.2240	0.9360	0.097*
H5B	0.4400	0.1358	0.8671	0.097*
C6	0.3485 (2)	0.0682 (5)	0.8228 (7)	0.0829 (10)
H6A	0.3520	0.1208	0.7190	0.099*
C7	0.2832 (2)	0.0858 (4)	0.8230 (6)	0.0583 (12)
C8	0.2566 (2)	0.1767 (4)	0.9332 (5)	0.0519 (11)
H8A	0.2857	0.2281	1.0017	0.062*
C9	0.1910 (2)	0.1910 (4)	0.9421 (5)	0.0504 (11)
H9A	0.1763	0.2521	1.0169	0.060*
C10	0.1431 (2)	0.1179 (4)	0.8435 (5)	0.0479 (7)
C11	0.1685 (2)	0.0266 (4)	0.7336 (5)	0.0498 (11)
H11A	0.1390	−0.0263	0.6687	0.060*
C12	0.2337 (2)	0.0142 (4)	0.7206 (5)	0.0506 (11)
H12A	0.2479	−0.0439	0.6408	0.061*
C13	−0.0292 (2)	0.0918 (4)	0.8074 (5)	0.0470 (10)
C14	−0.0524 (2)	0.1820 (4)	0.9173 (5)	0.0511 (11)
H14A	−0.0223	0.2352	0.9798	0.061*
C15	−0.1198 (2)	0.1937 (4)	0.9352 (6)	0.0588 (12)
H15A	−0.1348	0.2540	1.0108	0.071*
C16	−0.1639 (2)	0.1184 (4)	0.8440 (5)	0.0521 (11)
C17	−0.1442 (2)	0.0243 (4)	0.7373 (6)	0.0583 (12)
H17A	−0.1753	−0.0289	0.6783	0.070*
C18	−0.0770 (2)	0.0112 (4)	0.7203 (5)	0.0618 (12)
H18A	−0.0627	−0.0528	0.6493	0.074*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.100 (4)	0.112 (4)	0.104 (4)	0.046 (3)	0.004 (3)	−0.022 (3)
C1	0.064 (4)	0.138 (6)	0.118 (5)	0.009 (4)	0.005 (3)	−0.064 (5)
O1	0.058 (2)	0.128 (3)	0.105 (3)	−0.018 (2)	−0.005 (2)	0.007 (3)
O2	0.073 (2)	0.077 (3)	0.101 (3)	0.017 (2)	0.022 (2)	0.008 (2)
N2	0.0573 (17)	0.0468 (16)	0.0392 (14)	0.0041 (14)	0.0020 (13)	0.0020 (13)
N3	0.060 (2)	0.049 (2)	0.043 (2)	0.0021 (18)	−0.0003 (17)	0.0016 (17)
N4	0.060 (3)	0.061 (3)	0.076 (3)	0.004 (2)	0.004 (2)	0.023 (2)
C2	0.069 (2)	0.093 (2)	0.086 (2)	−0.0043 (17)	−0.0003 (17)	−0.010 (2)
C3	0.069 (2)	0.093 (2)	0.086 (2)	−0.0043 (17)	−0.0003 (17)	−0.010 (2)
C4	0.086 (4)	0.112 (5)	0.111 (5)	−0.048 (4)	−0.023 (4)	0.008 (4)
C5	0.042 (3)	0.110 (4)	0.091 (4)	−0.014 (3)	0.010 (3)	−0.046 (4)
C6	0.069 (2)	0.093 (2)	0.086 (2)	−0.0043 (17)	−0.0003 (17)	−0.010 (2)
C7	0.051 (3)	0.069 (3)	0.055 (3)	−0.007 (2)	−0.001 (2)	−0.017 (2)
C8	0.055 (3)	0.040 (2)	0.061 (3)	−0.007 (2)	0.006 (2)	−0.019 (2)
C9	0.064 (3)	0.047 (3)	0.041 (2)	−0.001 (2)	0.011 (2)	−0.014 (2)
C10	0.0573 (17)	0.0468 (16)	0.0392 (14)	0.0041 (14)	0.0020 (13)	0.0020 (13)
C11	0.052 (3)	0.052 (3)	0.044 (2)	0.003 (2)	−0.003 (2)	−0.005 (2)
C12	0.056 (3)	0.044 (2)	0.052 (3)	−0.001 (2)	0.000 (2)	−0.016 (2)
C13	0.059 (3)	0.044 (2)	0.038 (2)	0.005 (2)	0.0057 (19)	0.0108 (19)
C14	0.054 (3)	0.051 (3)	0.048 (3)	0.006 (2)	−0.002 (2)	−0.005 (2)
C15	0.070 (3)	0.056 (3)	0.051 (3)	0.012 (2)	0.005 (2)	−0.005 (2)
C16	0.065 (3)	0.048 (3)	0.044 (2)	0.002 (2)	0.007 (2)	0.014 (2)
C17	0.057 (3)	0.058 (3)	0.058 (3)	−0.005 (2)	−0.005 (2)	0.003 (2)
C18	0.075 (3)	0.066 (3)	0.045 (2)	0.001 (3)	0.003 (2)	−0.007 (2)

N1—C1	1.102 (6)	C6—H6A	0.9800
C1—C2	1.533 (7)	C7—C8	1.416 (5)
O1—N4	1.171 (5)	C7—C12	1.434 (5)
O2—N4	1.230 (5)	C8—C9	1.334 (5)
N2—N3	1.251 (4)	C8—H8A	0.9300
N2—C10	1.371 (5)	C9—C10	1.407 (5)
N3—C13	1.398 (5)	C9—H9A	0.9300
N4—C16	1.464 (6)	C10—C11	1.407 (5)
C2—C3	1.443 (6)	C11—C12	1.330 (5)
C2—H2B	0.9700	C11—H11A	0.9300
C2—H2C	0.9700	C12—H12A	0.9300
C3—C6	1.546 (7)	C13—C14	1.381 (5)
C3—H3B	0.9700	C13—C18	1.412 (6)
C3—H3C	0.9700	C14—C15	1.379 (5)
C4—C5	1.515 (7)	C14—H14A	0.9300
C4—H4A	0.9600	C15—C16	1.346 (6)
C4—H4B	0.9600	C15—H15A	0.9300
C4—H4C	0.9600	C16—C17	1.369 (6)
C5—C6	1.427 (6)	C17—C18	1.376 (6)
C5—H5A	0.9700	C17—H17A	0.9300
C5—H5B	0.9700	C18—H18A	0.9300
C6—C7	1.326 (6)

N1—C1—C2	166.2 (8)	C6—C7—C8	121.3 (4)
N3—N2—C10	114.5 (3)	C6—C7—C12	124.6 (4)
N2—N3—C13	112.7 (3)	C8—C7—C12	114.0 (4)
O1—N4—O2	122.0 (5)	C9—C8—C7	122.1 (4)
O1—N4—C16	120.3 (5)	C9—C8—H8A	118.9
O2—N4—C16	117.7 (5)	C7—C8—H8A	118.9
C3—C2—C1	107.1 (5)	C8—C9—C10	123.1 (4)
C3—C2—H2B	110.0	C8—C9—H9A	118.4
C1—C2—H2B	111.2	C10—C9—H9A	118.4
C3—C2—H2C	109.5	N2—C10—C9	117.9 (4)
C1—C2—H2C	110.4	N2—C10—C11	126.4 (4)
H2B—C2—H2C	108.6	C9—C10—C11	115.7 (4)
C2—C3—C6	109.1 (5)	C12—C11—C10	121.5 (4)
C2—C3—H3B	109.9	C12—C11—H11A	119.2
C6—C3—H3B	109.9	C10—C11—H11A	119.2
C2—C3—H3C	109.9	C11—C12—C7	123.4 (4)
C6—C3—H3C	109.9	C11—C12—H12A	118.3
H3B—C3—H3C	108.3	C7—C12—H12A	118.3
C5—C4—H4A	109.5	C14—C13—N3	126.6 (4)
C5—C4—H4B	109.5	C14—C13—C18	117.2 (4)
H4A—C4—H4B	109.5	N3—C13—C18	116.2 (4)
C5—C4—H4C	109.5	C15—C14—C13	120.5 (4)
H4A—C4—H4C	109.5	C15—C14—H14A	119.7
H4B—C4—H4C	109.5	C13—C14—H14A	119.7
C6—C5—C4	109.5 (5)	C16—C15—C14	120.3 (4)
C6—C5—H5A	109.8	C16—C15—H15A	119.8
C4—C5—H5A	109.8	C14—C15—H15A	119.8
C6—C5—H5B	109.8	C15—C16—C17	122.1 (4)
C4—C5—H5B	109.8	C15—C16—N4	120.1 (4)
H5A—C5—H5B	108.2	C17—C16—N4	117.7 (4)
C7—C6—C5	125.9 (5)	C16—C17—C18	117.8 (4)
C7—C6—C3	119.3 (5)	C16—C17—H17A	121.1
C5—C6—C3	113.8 (4)	C18—C17—H17A	121.1
C7—C6—H6A	93.4	C17—C18—C13	121.9 (4)
C5—C6—H6A	93.4	C17—C18—H18A	119.0
C3—C6—H6A	93.4	C13—C18—H18A	119.0

C10—N2—N3—C13	178.6 (3)	C10—C11—C12—C7	3.9 (6)
N1—C1—C2—C3	−168 (3)	C6—C7—C12—C11	174.3 (5)
C1—C2—C3—C6	165.2 (4)	C8—C7—C12—C11	−3.4 (6)
C4—C5—C6—C7	85.4 (7)	N2—N3—C13—C14	1.4 (5)
C4—C5—C6—C3	−82.7 (6)	N2—N3—C13—C18	−176.3 (3)
C2—C3—C6—C7	97.0 (6)	N3—C13—C14—C15	−179.6 (4)
C2—C3—C6—C5	−94.1 (6)	C18—C13—C14—C15	−2.0 (6)
C5—C6—C7—C8	−1.8 (9)	C13—C14—C15—C16	−0.8 (6)
C3—C6—C7—C8	165.7 (4)	C14—C15—C16—C17	3.1 (6)
C5—C6—C7—C12	−179.3 (5)	C14—C15—C16—N4	−176.9 (4)
C3—C6—C7—C12	−11.8 (8)	O1—N4—C16—C15	173.2 (4)
C6—C7—C8—C9	−176.3 (5)	O2—N4—C16—C15	−5.0 (6)
C12—C7—C8—C9	1.4 (6)	O1—N4—C16—C17	−6.8 (6)
C7—C8—C9—C10	−0.1 (7)	O2—N4—C16—C17	175.1 (4)
N3—N2—C10—C9	−178.4 (3)	C15—C16—C17—C18	−2.3 (6)
N3—N2—C10—C11	−0.3 (6)	N4—C16—C17—C18	177.6 (4)
C8—C9—C10—N2	178.7 (4)	C16—C17—C18—C13	−0.7 (6)
C8—C9—C10—C11	0.4 (6)	C14—C13—C18—C17	2.7 (6)
N2—C10—C11—C12	179.6 (4)	N3—C13—C18—C17	−179.4 (4)
C9—C10—C11—C12	−2.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···O1ⁱ	0.97	2.46	3.343 (6)	150
C9—H9A···Cg1ⁱⁱ	0.93	2.92	3.713 (6)	144
C15—H15A···Cg2ⁱⁱ	0.93	2.90	3.690 (6)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2C⋯O1ⁱ	0.97	2.46	3.343 (6)	150
C9—H9A⋯Cg1ⁱⁱ	0.93	2.92	3.713 (6)	144
C15—H15A⋯Cg2ⁱⁱ	0.93	2.90	3.690 (6)	143

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C7–C13 and C13–C18 rings, respectively.

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