4-Chloro-1-[2-(2-chloro­phen­yl)eth­yl]-2-nitro­benzene

Yashvanth Kumar, H.S.; Nagendra, P.; Siddaraju, B.P.; Chaluvaraju, K.C.; Byrappa, K.; Lokanath, N.K.; Madan Kumar, S.

doi:10.1107/S2414314616012049

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 7| July 2016| x161204

https://doi.org/10.1107/S2414314616012049

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4-Chloro-1-[2-(2-chlorophenyl)ethyl]-2-nitrobenzene

H. S. Yeshwanthkumar,^a P. Nagendra,^a B. P. Siddaraju,^b K. C. Chaluvaraju,^c K. Byrappa,^d N. K. Lokanath ^e and S. Madan Kumar ^f ^*

^aDepartment of Chemistry, Bharathi College, Bharathinagara, Mandya 571422, India, ^bDepartment of Engineering Chemistry, Cauvery Institute of Technology, Mandya 571 402, India, ^cDepartment of Pharmaceutical Chemistry, Government College of Pharmacy, P Kalinga Road, Bengaluru 560 027, India, ^dDepartment of Materials Science, Mangalagangotri, Mangalore University, Mangalore 574 199, India, ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^fPURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India
^*Correspondence e-mail: madan.mx@gmail.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 6 July 2016; accepted 24 July 2016; online 29 July 2016)

In the title compound, C₁₄H₁₁Cl₂NO₂, the dihedral angle between the phenyl rings is 8.60 (17)° and the nitro group makes a dihedral anle of 29.4 (4)° with its attached ring. The crystal structure features C—H⋯O hydrogen bonds and π–π interactions.

Keywords: crystal structure; nitrobenzene; intermolecular interactions.

CCDC reference: 1495647

Structure description

In continuation of our work on nitrobenzene derivatives, we report herein the crystal structure of the title compound (Anuradha et al., 2014 ).

In the title compound (Fig. 1), the dihedral angle between the phenyl rings is 8.60 (17)° and the nitro group makes a dihedral anle of 29.4 (4)° with its attached ring. The crystal structure (Fig. 2 and Table 1) features infinite chains of C4—H⋯O1 hydrogen bonds along the b axis and weak π–π interactions (Cg1⋯Cg2ⁱ = 3.672 (2) Å; Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively; symmetry code: (i) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.93	2.60	3.335 (5)	137
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Figure 1
A view of the title molecule, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
View along the b axis of the crystal packing of the title compound. Hydrogen bonds are drawn as dashed lines.

Synthesis and crystallization

The compound purchased from Sigma Aldrich and recrystallized from methanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₁Cl₂NO₂
M_r	296.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.5774 (15), 13.244 (3), 13.488 (3)
β (°)	97.157 (7)
V (Å³)	1343.0 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.48
Crystal size (mm)	0.3 × 0.23 × 0.12

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (NUMABS; Rigaku, 1999 )
T_min, T_max	0.874, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	8341, 2449, 1582
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.144, 1.04
No. of reflections	2449
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.44
Computer programs: CrystalClear SM Expert (Rigaku, 2011 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1495647

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616012049/vm4012sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616012049/vm4012Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616012049/vm4012Isup3.cml

checkCIF report

Computing details top

Data collection: CrystalClear SM Expert (Rigaku, 2011); cell refinement: CrystalClear SM Expert (Rigaku, 2011); data reduction: CrystalClear SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-Chloro-1-[2-(2-chlorophenyl)ethyl]-2-nitrobenzene top

Crystal data top

C₁₄H₁₁Cl₂NO₂	F(000) = 608
M_r = 296.14	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
a = 7.5774 (15) Å	Cell parameters from 2449 reflections
b = 13.244 (3) Å	θ = 3.0–25.3°
c = 13.488 (3) Å	µ = 0.48 mm⁻¹
β = 97.157 (7)°	T = 293 K
V = 1343.0 (5) Å³	Block, brown
Z = 4	0.3 × 0.23 × 0.12 mm

Data collection top

Rigaku Saturn724+ diffractometer	R_int = 0.064
profile data from ω–scans	θ_max = 25.4°, θ_min = 3.0°
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	h = −9→9
T_min = 0.874, T_max = 0.944	k = −15→15
8341 measured reflections	l = −16→16
2449 independent reflections	2449 standard reflections
1582 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0489P)² + 0.8842P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2449 reflections	Δρ_max = 0.31 e Å⁻³
172 parameters	Δρ_min = −0.44 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.08248 (14)	0.02730 (7)	0.87941 (8)	0.0724 (4)
Cl2	0.07879 (15)	0.41848 (11)	1.41515 (7)	0.0874 (4)
O1	0.3135 (5)	0.5551 (2)	1.0990 (2)	0.0927 (10)
O2	0.1992 (5)	0.4658 (2)	0.9772 (2)	0.1112 (12)
N1	0.2398 (4)	0.4794 (2)	1.0660 (2)	0.0645 (9)
C1	0.1915 (4)	0.4026 (2)	1.1368 (2)	0.0431 (8)
C2	0.1617 (4)	0.4389 (3)	1.2292 (2)	0.0492 (8)
H2	0.1729	0.5075	1.2435	0.059*
C3	0.1157 (4)	0.3734 (3)	1.2988 (2)	0.0511 (9)
C4	0.1024 (5)	0.2721 (3)	1.2787 (3)	0.0578 (10)
H4	0.0714	0.2271	1.3265	0.069*
C5	0.1357 (5)	0.2381 (3)	1.1866 (3)	0.0542 (9)
H5	0.1274	0.1691	1.1740	0.065*
C6	0.1811 (4)	0.3011 (3)	1.1111 (2)	0.0444 (8)
C7	0.2166 (4)	0.2570 (3)	1.0130 (2)	0.0546 (9)
H7A	0.2666	0.1899	1.0243	0.066*
H7B	0.3037	0.2984	0.9850	0.066*
C8	0.0476 (4)	0.2502 (3)	0.9375 (2)	0.0527 (9)
H8A	−0.0301	0.1985	0.9590	0.063*
H8B	−0.0153	0.3141	0.9360	0.063*
C9	0.0892 (4)	0.2255 (3)	0.8342 (2)	0.0441 (8)
C10	0.1097 (4)	0.1285 (3)	0.8002 (2)	0.0463 (8)
C11	0.1495 (5)	0.1080 (3)	0.7050 (3)	0.0588 (10)
H11	0.1628	0.0415	0.6850	0.071*
C12	0.1691 (5)	0.1851 (4)	0.6406 (3)	0.0688 (12)
H12	0.1936	0.1717	0.5760	0.083*
C13	0.1521 (5)	0.2835 (4)	0.6720 (3)	0.0717 (12)
H13	0.1675	0.3367	0.6289	0.086*
C14	0.1126 (5)	0.3027 (3)	0.7667 (3)	0.0583 (10)
H14	0.1010	0.3694	0.7865	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0822 (7)	0.0552 (6)	0.0777 (7)	−0.0030 (5)	0.0022 (5)	0.0056 (5)
Cl2	0.0788 (7)	0.1404 (11)	0.0451 (5)	0.0111 (7)	0.0157 (5)	−0.0200 (6)
O1	0.138 (3)	0.0512 (17)	0.087 (2)	−0.0271 (19)	0.0045 (19)	0.0057 (15)
O2	0.181 (4)	0.105 (3)	0.0490 (18)	−0.049 (2)	0.020 (2)	0.0081 (17)
N1	0.084 (2)	0.054 (2)	0.056 (2)	−0.0080 (19)	0.0109 (17)	0.0006 (16)
C1	0.0464 (19)	0.0454 (19)	0.0375 (17)	0.0016 (16)	0.0053 (14)	0.0019 (15)
C2	0.051 (2)	0.0474 (19)	0.048 (2)	0.0021 (17)	−0.0005 (16)	−0.0103 (17)
C3	0.042 (2)	0.072 (3)	0.0390 (18)	0.0055 (18)	0.0051 (15)	−0.0066 (17)
C4	0.054 (2)	0.071 (3)	0.048 (2)	0.001 (2)	0.0039 (17)	0.0152 (19)
C5	0.056 (2)	0.044 (2)	0.060 (2)	0.0032 (18)	−0.0034 (18)	0.0009 (17)
C6	0.0382 (19)	0.052 (2)	0.0420 (18)	0.0050 (16)	0.0001 (14)	−0.0092 (16)
C7	0.050 (2)	0.063 (2)	0.049 (2)	0.0100 (19)	−0.0002 (17)	−0.0189 (17)
C8	0.048 (2)	0.060 (2)	0.048 (2)	0.0060 (18)	0.0025 (16)	−0.0140 (17)
C9	0.0397 (18)	0.050 (2)	0.0406 (18)	0.0051 (16)	−0.0029 (14)	−0.0055 (15)
C10	0.0419 (19)	0.048 (2)	0.0474 (19)	−0.0017 (16)	−0.0012 (15)	−0.0057 (15)
C11	0.055 (2)	0.070 (3)	0.052 (2)	0.001 (2)	0.0063 (17)	−0.024 (2)
C12	0.055 (2)	0.111 (4)	0.041 (2)	−0.010 (2)	0.0065 (17)	−0.014 (2)
C13	0.062 (3)	0.096 (3)	0.055 (2)	−0.017 (2)	−0.0012 (19)	0.018 (2)
C14	0.057 (2)	0.057 (2)	0.059 (2)	0.0012 (19)	−0.0039 (18)	0.0000 (19)

Geometric parameters (Å, º) top

Cl1—C10	1.742 (4)	C7—H7B	0.9700
Cl2—C3	1.734 (3)	C7—C8	1.536 (4)
O1—N1	1.206 (4)	C8—H8A	0.9700
O2—N1	1.212 (4)	C8—H8B	0.9700
N1—C1	1.471 (4)	C8—C9	1.503 (4)
C1—C2	1.380 (4)	C9—C10	1.380 (4)
C1—C6	1.388 (4)	C9—C14	1.395 (5)
C2—H2	0.9300	C10—C11	1.381 (4)
C2—C3	1.356 (5)	C11—H11	0.9300
C3—C4	1.370 (5)	C11—C12	1.361 (5)
C4—H4	0.9300	C12—H12	0.9300
C4—C5	1.373 (5)	C12—C13	1.380 (6)
C5—H5	0.9300	C13—H13	0.9300
C5—C6	1.394 (5)	C13—C14	1.371 (5)
C6—C7	1.501 (4)	C14—H14	0.9300
C7—H7A	0.9700

O1—N1—O2	122.4 (3)	C8—C7—H7B	109.1
O1—N1—C1	118.5 (3)	C7—C8—H8A	109.2
O2—N1—C1	119.1 (3)	C7—C8—H8B	109.2
C2—C1—N1	115.3 (3)	H8A—C8—H8B	107.9
C2—C1—C6	123.5 (3)	C9—C8—C7	111.9 (3)
C6—C1—N1	121.2 (3)	C9—C8—H8A	109.2
C1—C2—H2	120.4	C9—C8—H8B	109.2
C3—C2—C1	119.2 (3)	C10—C9—C8	123.8 (3)
C3—C2—H2	120.4	C10—C9—C14	115.9 (3)
C2—C3—Cl2	119.4 (3)	C14—C9—C8	120.3 (3)
C2—C3—C4	120.6 (3)	C9—C10—Cl1	119.1 (3)
C4—C3—Cl2	120.0 (3)	C9—C10—C11	122.6 (3)
C3—C4—H4	120.6	C11—C10—Cl1	118.4 (3)
C3—C4—C5	118.9 (3)	C10—C11—H11	120.0
C5—C4—H4	120.6	C12—C11—C10	120.0 (4)
C4—C5—H5	118.2	C12—C11—H11	120.0
C4—C5—C6	123.7 (3)	C11—C12—H12	120.3
C6—C5—H5	118.2	C11—C12—C13	119.4 (3)
C1—C6—C5	114.1 (3)	C13—C12—H12	120.3
C1—C6—C7	125.9 (3)	C12—C13—H13	120.0
C5—C6—C7	119.9 (3)	C14—C13—C12	120.0 (4)
C6—C7—H7A	109.1	C14—C13—H13	120.0
C6—C7—H7B	109.1	C9—C14—H14	118.9
C6—C7—C8	112.4 (3)	C13—C14—C9	122.1 (4)
H7A—C7—H7B	107.9	C13—C14—H14	118.9
C8—C7—H7A	109.1

Cl1—C10—C11—C12	179.0 (3)	C4—C5—C6—C7	179.5 (3)
Cl2—C3—C4—C5	−178.7 (3)	C5—C6—C7—C8	89.9 (4)
O1—N1—C1—C2	27.5 (5)	C6—C1—C2—C3	−1.5 (5)
O1—N1—C1—C6	−151.4 (4)	C6—C7—C8—C9	168.7 (3)
O2—N1—C1—C2	−150.2 (4)	C7—C8—C9—C10	86.1 (4)
O2—N1—C1—C6	30.9 (5)	C7—C8—C9—C14	−92.7 (4)
N1—C1—C2—C3	179.7 (3)	C8—C9—C10—Cl1	1.2 (4)
N1—C1—C6—C5	179.4 (3)	C8—C9—C10—C11	−179.5 (3)
N1—C1—C6—C7	0.4 (5)	C8—C9—C14—C13	179.5 (3)
C1—C2—C3—Cl2	179.8 (2)	C9—C10—C11—C12	−0.3 (5)
C1—C2—C3—C4	1.3 (5)	C10—C9—C14—C13	0.5 (5)
C1—C6—C7—C8	−91.2 (4)	C10—C11—C12—C13	1.2 (6)
C2—C1—C6—C5	0.6 (5)	C11—C12—C13—C14	−1.2 (6)
C2—C1—C6—C7	−178.4 (3)	C12—C13—C14—C9	0.4 (6)
C2—C3—C4—C5	−0.3 (5)	C14—C9—C10—Cl1	−179.9 (2)
C3—C4—C5—C6	−0.6 (5)	C14—C9—C10—C11	−0.5 (5)
C4—C5—C6—C1	0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.60	3.335 (5)	137
C7—H7B···O2	0.97	2.35	2.808 (5)	108
C8—H8A···Cl1	0.97	2.69	3.074 (4)	104

Symmetry code: (i) −x+1/2, y−1/2, −z+5/2.

Acknowledgements

The authors thank the DST–PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility. PN and YHS acknowledge Bharthi College, Maddur, for research facilities.

References

Anuradha, V., Madan Kumar, S., Siddaraju, B. P., Lokanath, N. K. & Nagendra, P. (2014). Acta Cryst. E70, o616. CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2011). CrystalClear SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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