(E)-1-[4-(3-Bromo­prop­oxy)phen­yl]-2-p-tolyl­diazene

Yu, Z.-X.; Li, B.

doi:10.1107/S1600536812021538

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1761

doi:10.1107/S1600536812021538

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(E)-1-[4-(3-Bromopropoxy)phenyl]-2-p-tolyldiazene

Zhen-Xiang Yu ^a ^* and Bao Li ^b

^aDepartment of Respiratory Medicine, First Hospital, Jilin University, Changchun 130021, People's Republic of China, and ^bState Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: yuzhenxiang2005@hotmail.com

(Received 6 May 2012; accepted 11 May 2012; online 16 May 2012)

In the title molecule, C₁₆H₁₇BrN₂O, the benzene rings, bridged by a diazene fragment, form a dihedral angle of 6.3 (2)°. The crystal packing exhibits relatively short Br⋯Br contacts of 3.6989 (14) Å.

Related literature

For the crystal structure of (E)-4-(p-tolydiazenyl)phenol, see: Petek et al. (2006 ). For details of the synthesis, see: Badawi et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₇BrN₂O
M_r = 333.23
Monoclinic, P 2₁ /c
a = 26.530 (15) Å
b = 4.785 (2) Å
c = 11.810 (7) Å
β = 102.85 (2)°
V = 1461.8 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.81 mm⁻¹
T = 293 K
0.24 × 0.23 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.553, T_max = 0.574
13590 measured reflections
3337 independent reflections
1860 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.180
S = 1.01
3337 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021538/cv5298sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021538/cv5298Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021538/cv5298Isup3.cml

checkCIF report

Comment top

The azobenzene and its derivate have been widely investigated due to the trans-cis transformations of N=N double bond caused by heating, light or other effects. Herein, we report the crystal structure of the title compound (I), which is a new derivate of azobenzene.

In (I) (Fig. 1), all bond lengths and angles are in normal ranges and comparable with those in similar structure (Petek et al., 2006). The dihedral angle between the two aromatic rings is 6.3 (2)°. The crystal packing exhibits relatively short intermolecular Br···Br contacts of 3.6989 (14) Å.

Related literature top

For the crystal structure of (E)-4-(p-tolydiazenyl)phenol, see: Petek et al. (2006). For details of the synthesis, see: Badawi et al. (2006).

Experimental top

The title compound was prepared by refluxing 4-((4-methylphenyl)azo)phenol with 1,3-dibromopropane in acetone according to the known procedure (Badawi et al. 2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation method at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 30% probalility level.

(E)-1-[4-(3-Bromopropoxy)phenyl]-2-p-tolyldiazene top

Crystal data top

C₁₆H₁₇BrN₂O	F(000) = 680
M_r = 333.23	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6956 reflections
a = 26.530 (15) Å	θ = 3.4–27.5°
b = 4.785 (2) Å	µ = 2.81 mm⁻¹
c = 11.810 (7) Å	T = 293 K
β = 102.85 (2)°	Block, yellow
V = 1461.8 (13) Å³	0.24 × 0.23 × 0.22 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3337 independent reflections
Radiation source: fine-focus sealed tube	1860 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −34→33
T_min = 0.553, T_max = 0.574	k = −6→6
13590 measured reflections	l = −15→15

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0906P)²] where P = (F_o² + 2F_c²)/3
3337 reflections	(Δ/σ)_max = 0.012
182 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₁₇BrN₂O	V = 1461.8 (13) Å³
M_r = 333.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 26.530 (15) Å	µ = 2.81 mm⁻¹
b = 4.785 (2) Å	T = 293 K
c = 11.810 (7) Å	0.24 × 0.23 × 0.22 mm
β = 102.85 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3337 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1860 reflections with I > 2σ(I)
T_min = 0.553, T_max = 0.574	R_int = 0.080
13590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.01	Δρ_max = 0.40 e Å⁻³
3337 reflections	Δρ_min = −0.59 e Å⁻³
182 parameters

Special details top

Experimental. (See detailed section in the paper)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.03507 (2)	1.74980 (10)	0.35896 (4)	0.0780 (3)
C1	0.07293 (17)	1.5076 (9)	0.4814 (4)	0.0666 (12)
H1A	0.0493	1.3736	0.5031	0.080*
H1B	0.0990	1.4048	0.4527	0.080*
C2	0.09770 (19)	1.6700 (8)	0.5834 (4)	0.0638 (12)
H2A	0.0716	1.7772	0.6102	0.077*
H2B	0.1219	1.8008	0.5617	0.077*
C3	0.12642 (16)	1.4854 (7)	0.6820 (3)	0.0555 (10)
H3A	0.1414	1.5984	0.7493	0.067*
H3B	0.1029	1.3514	0.7042	0.067*
C4	0.19783 (14)	1.1643 (7)	0.7148 (3)	0.0438 (8)
C5	0.23339 (14)	1.0199 (7)	0.6659 (3)	0.0461 (9)
H5	0.2351	1.0542	0.5893	0.055*
C6	0.26574 (16)	0.8279 (7)	0.7304 (3)	0.0475 (9)
H6	0.2897	0.7334	0.6977	0.057*
C7	0.26299 (16)	0.7723 (6)	0.8464 (4)	0.0436 (9)
C8	0.22842 (15)	0.9224 (7)	0.8937 (3)	0.0486 (9)
H8	0.2272	0.8924	0.9708	0.058*
C9	0.19546 (15)	1.1169 (7)	0.8291 (3)	0.0475 (9)
H9	0.1720	1.2144	0.8621	0.057*
C10	0.35721 (16)	0.2505 (6)	0.9470 (3)	0.0426 (8)
C11	0.39446 (15)	0.1260 (8)	0.8990 (3)	0.0498 (9)
H11	0.3969	0.1742	0.8241	0.060*
C12	0.42806 (15)	−0.0681 (7)	0.9600 (3)	0.0490 (9)
H12	0.4531	−0.1474	0.9260	0.059*
C13	0.42526 (14)	−0.1473 (7)	1.0710 (3)	0.0395 (8)
C14	0.38674 (14)	−0.0307 (7)	1.1179 (3)	0.0453 (9)
H14	0.3832	−0.0870	1.1911	0.054*
C15	0.35311 (15)	0.1696 (7)	1.0573 (3)	0.0470 (9)
H15	0.3279	0.2489	1.0909	0.056*
C16	0.46205 (15)	−0.3593 (9)	1.1367 (3)	0.0514 (10)
H16A	0.4653	−0.3327	1.2186	0.077*
H16B	0.4953	−0.3373	1.1183	0.077*
H16C	0.4491	−0.5438	1.1154	0.077*
N1	0.29418 (12)	0.5728 (6)	0.9213 (3)	0.0476 (8)
N2	0.32604 (13)	0.4536 (6)	0.8743 (3)	0.0474 (8)
O1	0.16630 (11)	1.3435 (5)	0.6400 (2)	0.0526 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0757 (4)	0.0956 (5)	0.0551 (3)	−0.0036 (3)	−0.0017 (3)	0.0109 (2)
C1	0.059 (3)	0.072 (3)	0.064 (3)	0.003 (2)	0.005 (2)	0.000 (2)
C2	0.064 (3)	0.057 (2)	0.062 (3)	0.011 (2)	−0.003 (2)	−0.004 (2)
C3	0.056 (3)	0.052 (2)	0.056 (2)	0.0144 (19)	0.005 (2)	−0.0005 (18)
C4	0.038 (2)	0.0410 (17)	0.048 (2)	−0.0028 (15)	0.0019 (17)	−0.0006 (16)
C5	0.046 (2)	0.052 (2)	0.0408 (19)	−0.0021 (17)	0.0106 (17)	0.0005 (17)
C6	0.043 (2)	0.0473 (19)	0.052 (2)	0.0040 (16)	0.0107 (18)	−0.0037 (16)
C7	0.044 (2)	0.0375 (17)	0.046 (2)	−0.0043 (16)	0.0021 (17)	0.0009 (15)
C8	0.055 (2)	0.047 (2)	0.045 (2)	−0.0017 (18)	0.0115 (18)	0.0027 (16)
C9	0.045 (2)	0.0459 (18)	0.051 (2)	0.0026 (17)	0.0104 (18)	0.0006 (17)
C10	0.045 (2)	0.0383 (17)	0.0410 (19)	0.0010 (16)	0.0025 (17)	0.0022 (15)
C11	0.055 (3)	0.055 (2)	0.039 (2)	0.0079 (19)	0.0093 (18)	0.0049 (17)
C12	0.053 (2)	0.050 (2)	0.046 (2)	0.0090 (18)	0.0162 (18)	0.0032 (17)
C13	0.044 (2)	0.0343 (16)	0.0392 (19)	−0.0036 (15)	0.0063 (16)	−0.0017 (14)
C14	0.052 (2)	0.0468 (19)	0.0373 (19)	−0.0034 (17)	0.0109 (17)	−0.0010 (16)
C15	0.043 (2)	0.0472 (18)	0.052 (2)	0.0009 (16)	0.0138 (19)	−0.0076 (16)
C16	0.049 (2)	0.0476 (19)	0.055 (2)	0.0024 (18)	0.005 (2)	0.0058 (17)
N1	0.0466 (19)	0.0482 (17)	0.0462 (18)	−0.0038 (15)	0.0068 (15)	−0.0052 (14)
N2	0.0490 (19)	0.0426 (16)	0.0492 (18)	−0.0005 (14)	0.0078 (15)	−0.0032 (14)
O1	0.0480 (17)	0.0547 (14)	0.0530 (16)	0.0102 (13)	0.0070 (13)	0.0100 (13)

Geometric parameters (Å, º) top

Br1—C1	1.948 (4)	C7—N1	1.433 (5)
Br1—Br1ⁱ	3.6989 (14)	C8—C9	1.384 (5)
Br1—Br1ⁱⁱ	3.6989 (14)	C8—H8	0.9300
C1—C2	1.461 (6)	C9—H9	0.9300
C1—H1A	0.9700	C10—C11	1.379 (5)
C1—H1B	0.9700	C10—C15	1.387 (5)
C2—C3	1.524 (5)	C10—N2	1.432 (4)
C2—H2A	0.9700	C11—C12	1.375 (5)
C2—H2B	0.9700	C11—H11	0.9300
C3—O1	1.435 (4)	C12—C13	1.382 (5)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.383 (5)
C4—O1	1.373 (5)	C13—C16	1.499 (5)
C4—C9	1.384 (5)	C14—C15	1.394 (5)
C4—C5	1.395 (5)	C14—H14	0.9300
C5—C6	1.367 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.413 (5)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—C8	1.378 (5)	N1—N2	1.248 (4)

C1—Br1—Br1ⁱ	103.19 (13)	C7—C8—C9	121.6 (4)
C1—Br1—Br1ⁱⁱ	176.05 (13)	C7—C8—H8	119.2
Br1ⁱ—Br1—Br1ⁱⁱ	80.61 (4)	C9—C8—H8	119.2
C2—C1—Br1	111.0 (3)	C4—C9—C8	119.2 (4)
C2—C1—H1A	109.4	C4—C9—H9	120.4
Br1—C1—H1A	109.4	C8—C9—H9	120.4
C2—C1—H1B	109.4	C11—C10—C15	118.6 (3)
Br1—C1—H1B	109.4	C11—C10—N2	114.7 (3)
H1A—C1—H1B	108.0	C15—C10—N2	126.7 (3)
C1—C2—C3	112.2 (3)	C12—C11—C10	121.1 (3)
C1—C2—H2A	109.2	C12—C11—H11	119.5
C3—C2—H2A	109.2	C10—C11—H11	119.5
C1—C2—H2B	109.2	C11—C12—C13	121.1 (3)
C3—C2—H2B	109.2	C11—C12—H12	119.4
H2A—C2—H2B	107.9	C13—C12—H12	119.4
O1—C3—C2	107.0 (3)	C14—C13—C12	118.0 (3)
O1—C3—H3A	110.3	C14—C13—C16	121.3 (3)
C2—C3—H3A	110.3	C12—C13—C16	120.7 (3)
O1—C3—H3B	110.3	C13—C14—C15	121.2 (3)
C2—C3—H3B	110.3	C13—C14—H14	119.4
H3A—C3—H3B	108.6	C15—C14—H14	119.4
O1—C4—C9	125.2 (3)	C10—C15—C14	119.9 (3)
O1—C4—C5	114.5 (3)	C10—C15—H15	120.0
C9—C4—C5	120.3 (3)	C14—C15—H15	120.0
C6—C5—C4	120.1 (3)	C13—C16—H16A	109.5
C6—C5—H5	120.0	C13—C16—H16B	109.5
C4—C5—H5	120.0	H16A—C16—H16B	109.5
C5—C6—C7	120.3 (3)	C13—C16—H16C	109.5
C5—C6—H6	119.8	H16A—C16—H16C	109.5
C7—C6—H6	119.8	H16B—C16—H16C	109.5
C8—C7—C6	118.5 (3)	N2—N1—C7	112.6 (3)
C8—C7—N1	116.2 (3)	N1—N2—C10	113.7 (3)
C6—C7—N1	125.2 (3)	C4—O1—C3	117.6 (3)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇BrN₂O
M_r	333.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	26.530 (15), 4.785 (2), 11.810 (7)
β (°)	102.85 (2)
V (Å³)	1461.8 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.81
Crystal size (mm)	0.24 × 0.23 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.553, 0.574
No. of measured, independent and observed [I > 2σ(I)] reflections	13590, 3337, 1860
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.180, 1.01
No. of reflections	3337
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.59

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Badawi, A. M., Azzam, E. M. S. & Morsy, S. M. (2006). Bioorg. Med. Chem. 14, 8661–8665. Web of Science CrossRef PubMed CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Petek, H., Erşahin, F., Albayrak, Ç., Ağar, E. & Şenel, İ. (2006). Acta Cryst. E62, o5874–o5875. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar