4-Chloro-2-nitro-1-(2-phenyl­eth­yl)benzene

Manjunath, N.K.; Nabil Najib, A.A.; Nagendra, P.; Siddaraju, B.P.; Swamy, M.T.; Byrappa, K.; Madan Kumar, S.

doi:10.1107/S2414314617005478

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170547

https://doi.org/10.1107/S2414314617005478

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4-Chloro-2-nitro-1-(2-phenylethyl)benzene

N. K. Manjunath,^a A. A. Nabil Najib,^b P. Nagendra,^c B. P Siddaraju,^d M. T. Swamy,^e K. Byrappa ^f and S. Madan Kumar ^g ^*

^aDepartment of Chemistry, Shri Pillappa College of Engineering, Bengaluru 560 089, India, ^bPhysics and Basic Science Department, Faculty of Engineering Technology, Albalqa Applied University, Amman 11134, Jordan, ^cDepartment of Chemistry, Bharathi College, Bharthi Nagara, Mandya 571 422, India, ^dDepartment of Chemistry, Cauvery Institute of Technology, Mandya 571 401, India, ^eDepartment of Chemistry, Sambhram Institute of Technology, Bengaluru 560 097, India, ^fDepartment of Material Science, Mangalore University, Mangaluru 574 199, India, and ^gPURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India
^*Correspondence e-mail: madan.mx@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 March 2017; accepted 11 April 2017; online 21 April 2017)

In the title compound, C₁₄H₁₂ClNO₂, the dihedral angle between the aromatic rings is 6.09 (17)° and the C_ar—C—C—C_ar torsion angle is −179.4 (3)°. The nitro group is close to coplanar with its attached ring [dihedral angle = 7.9 (2)°] and the Cl atom is disordered over two adjacent sites in a 0.54 (4):0.46 (4) ratio. In the crystal, C—H⋯O hydrogen bonds link the molecules into C(6) [001] chains.

Keywords: crystal structure; 4-chloro-2-nitro-1-(2-phenylethyl); C—H⋯O hydrogen bond.

CCDC reference: 1543429

Structure description

As part of out interest in the synthesis and crystal structures of 4-chloronitrobenzene derivatives, the title compound (Fig. 1) is reported here.

Figure 1
A view of the title molecule, with displacement ellipsoids drawn at the 50% probability level.

The dihedral angle between the aromatic rings is 6.09 (17)° and the C6—C7—C8—C9 torsion angle is −179.4 (3)°. The nitro group is close to being coplanar with its attached ring [dihedral angle = 7.9 (2)°]. In the crystal, C—H⋯O hydrogen bonds (Table 1) link the molecules into C(6) [001] chains (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.54	3.462 (5)	175
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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

Synthesis and crystallization

4-Chloronitrobenzene (1.57 g, 0.01 mol) was dissolved in 25 ml of ethanol and styrene (1.04 g, 0.01 mol) was dissolved in 25 ml of ethanol. The solutions were mixed and stirred in a beaker at 30° C for 1 h. The mixture was kept aside for two days at room temperature. The formed product was filtered and dried in a vacuum desiccator over phosphorous pentoxide. The product was recrystallized from toluene solution by slow evaporation (m.p. 399–401 K) in the form of colourless blocks.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The Cl atom is disordered over two adjacent sites in a 0.54 (4):0.46 (4) ratio.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO₂
M_r	261.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.201 (3), 7.3285 (12), 12.974 (4)
β (°)	105.89 (2)
V (Å³)	1298.6 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.19 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (NUMABS; Rigaku, 1999 )
T_min, T_max	0.947, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13474, 2554, 1389
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.220, 1.04
No. of reflections	2554
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18
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: 1543429

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005478/hb4131sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005478/hb4131Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005478/hb4131Isup3.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-2-nitro-1-(2-phenylethyl)benzene top

Crystal data top

C₁₄H₁₂ClNO₂	D_x = 1.338 Mg m⁻³
M_r = 261.70	Melting point: 399 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.201 (3) Å	Cell parameters from 2554 reflections
b = 7.3285 (12) Å	θ = 3–52°
c = 12.974 (4) Å	µ = 0.29 mm⁻¹
β = 105.89 (2)°	T = 293 K
V = 1298.6 (5) Å³	Block, colourless
Z = 4	0.19 × 0.18 × 0.15 mm
F(000) = 544

Data collection top

Rigaku Saturn724+ diffractometer	R_int = 0.095
profile data from ω–scans	θ_max = 26.0°, θ_min = 3.0°
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	h = −17→17
T_min = 0.947, T_max = 0.960	k = −9→9
13474 measured reflections	l = −16→15
2554 independent reflections	2554 standard reflections
1389 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.220	w = 1/[σ²(F_o²) + (0.095P)² + 0.1859P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2554 reflections	Δρ_max = 0.18 e Å⁻³
173 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints

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	Occ. (<1)
Cl1	0.4908 (4)	−0.3295 (6)	0.5958 (8)	0.101 (2)	0.54 (4)
O1	0.7685 (3)	0.1384 (5)	0.4195 (2)	0.1401 (13)
O2	0.6890 (3)	−0.0951 (6)	0.3611 (3)	0.1827 (18)
N1	0.7168 (2)	0.0150 (5)	0.4293 (2)	0.0921 (9)
C1	0.6844 (2)	−0.0018 (4)	0.5279 (2)	0.0626 (8)
C2	0.6156 (2)	−0.1349 (4)	0.5248 (3)	0.0736 (9)
H2	0.5927	−0.2064	0.4639	0.088*
C3	0.5815 (2)	−0.1608 (4)	0.6111 (3)	0.0827 (10)
C4	0.6153 (3)	−0.0577 (5)	0.6996 (3)	0.1003 (12)
H4	0.5917	−0.0757	0.7590	0.120*
C5	0.6847 (3)	0.0743 (5)	0.7018 (3)	0.0945 (11)
H5	0.7069	0.1447	0.7633	0.113*
C6	0.7228 (2)	0.1067 (4)	0.6156 (2)	0.0675 (8)
C7	0.7986 (2)	0.2541 (4)	0.6279 (3)	0.0842 (10)
H7A	0.8439	0.2210	0.5871	0.101*
H7B	0.8354	0.2624	0.7027	0.101*
C8	0.7545 (2)	0.4399 (4)	0.5905 (3)	0.0904 (11)
H8A	0.7173	0.4317	0.5158	0.108*
H8B	0.7098	0.4740	0.6318	0.108*
C9	0.8315 (2)	0.5853 (4)	0.6023 (3)	0.0736 (9)
C10	0.8801 (3)	0.6110 (5)	0.5244 (3)	0.0948 (11)
H10	0.8641	0.5391	0.4630	0.114*
C11	0.9520 (3)	0.7420 (6)	0.5368 (3)	0.1023 (12)
H11	0.9830	0.7582	0.4829	0.123*
C12	0.9783 (3)	0.8470 (5)	0.6250 (3)	0.0918 (11)
H12	1.0273	0.9342	0.6325	0.110*
C13	0.9318 (3)	0.8232 (4)	0.7035 (3)	0.0874 (11)
H13	0.9491	0.8954	0.7647	0.105*
C14	0.8591 (2)	0.6926 (4)	0.6925 (3)	0.0790 (9)
H14	0.8286	0.6773	0.7468	0.095*
Cl1A	0.5021 (10)	−0.3187 (16)	0.634 (3)	0.169 (4)	0.46 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0740 (19)	0.069 (3)	0.161 (4)	−0.0124 (12)	0.031 (2)	0.015 (3)
O1	0.171 (3)	0.143 (3)	0.132 (2)	−0.030 (2)	0.084 (2)	0.025 (2)
O2	0.236 (4)	0.223 (4)	0.114 (2)	−0.069 (4)	0.089 (3)	−0.069 (3)
N1	0.100 (2)	0.102 (2)	0.080 (2)	0.0064 (18)	0.0352 (17)	−0.0007 (18)
C1	0.0647 (18)	0.0570 (16)	0.0696 (18)	0.0061 (13)	0.0240 (14)	0.0066 (14)
C2	0.0651 (19)	0.0626 (18)	0.090 (2)	0.0003 (14)	0.0151 (17)	−0.0029 (16)
C3	0.069 (2)	0.0570 (19)	0.130 (3)	0.0019 (15)	0.041 (2)	0.0143 (19)
C4	0.133 (3)	0.076 (2)	0.118 (3)	0.008 (2)	0.077 (3)	0.013 (2)
C5	0.142 (3)	0.068 (2)	0.080 (2)	−0.004 (2)	0.040 (2)	−0.0088 (17)
C6	0.0700 (19)	0.0542 (17)	0.077 (2)	−0.0004 (14)	0.0180 (16)	0.0046 (15)
C7	0.074 (2)	0.065 (2)	0.106 (2)	−0.0045 (16)	0.0099 (18)	0.0105 (18)
C8	0.076 (2)	0.0575 (19)	0.134 (3)	−0.0004 (15)	0.022 (2)	0.0109 (19)
C9	0.0648 (19)	0.0514 (17)	0.101 (2)	0.0005 (14)	0.0160 (17)	0.0065 (17)
C10	0.105 (3)	0.080 (2)	0.100 (3)	−0.018 (2)	0.030 (2)	−0.0054 (19)
C11	0.102 (3)	0.096 (3)	0.118 (3)	−0.020 (2)	0.046 (2)	0.010 (3)
C12	0.078 (2)	0.073 (2)	0.116 (3)	−0.0160 (17)	0.014 (2)	0.016 (2)
C13	0.086 (3)	0.066 (2)	0.100 (3)	−0.0012 (17)	0.008 (2)	0.0001 (18)
C14	0.075 (2)	0.063 (2)	0.101 (2)	0.0045 (16)	0.0282 (18)	0.0085 (18)
Cl1A	0.103 (4)	0.162 (6)	0.252 (12)	−0.030 (3)	0.068 (5)	0.083 (5)

Geometric parameters (Å, º) top

Cl1—C3	1.757 (6)	C7—H7B	0.9700
O1—N1	1.193 (4)	C7—C8	1.521 (4)
O2—N1	1.182 (4)	C8—H8A	0.9700
N1—C1	1.479 (4)	C8—H8B	0.9700
C1—C2	1.374 (4)	C8—C9	1.505 (4)
C1—C6	1.373 (4)	C9—C10	1.384 (5)
C2—H2	0.9300	C9—C14	1.374 (4)
C2—C3	1.350 (5)	C10—H10	0.9300
C3—C4	1.348 (5)	C10—C11	1.378 (5)
C3—Cl1A	1.697 (9)	C11—H11	0.9300
C4—H4	0.9300	C11—C12	1.344 (5)
C4—C5	1.376 (5)	C12—H12	0.9300
C5—H5	0.9300	C12—C13	1.369 (5)
C5—C6	1.389 (5)	C13—H13	0.9300
C6—C7	1.502 (4)	C13—C14	1.386 (4)
C7—H7A	0.9700	C14—H14	0.9300

O1—N1—C1	120.1 (3)	C8—C7—H7A	109.0
O2—N1—O1	121.8 (4)	C8—C7—H7B	109.0
O2—N1—C1	118.1 (3)	C7—C8—H8A	109.2
C2—C1—N1	114.9 (3)	C7—C8—H8B	109.2
C6—C1—N1	121.5 (3)	H8A—C8—H8B	107.9
C6—C1—C2	123.6 (3)	C9—C8—C7	112.2 (3)
C1—C2—H2	120.3	C9—C8—H8A	109.2
C3—C2—C1	119.3 (3)	C9—C8—H8B	109.2
C3—C2—H2	120.3	C10—C9—C8	121.0 (3)
C2—C3—Cl1	115.1 (4)	C14—C9—C8	121.5 (3)
C2—C3—Cl1A	130.3 (12)	C14—C9—C10	117.5 (3)
C4—C3—Cl1	124.7 (4)	C9—C10—H10	119.6
C4—C3—C2	120.2 (3)	C11—C10—C9	120.7 (3)
C4—C3—Cl1A	109.4 (12)	C11—C10—H10	119.6
C3—C4—H4	120.1	C10—C11—H11	119.3
C3—C4—C5	119.8 (3)	C12—C11—C10	121.5 (4)
C5—C4—H4	120.1	C12—C11—H11	119.3
C4—C5—H5	118.7	C11—C12—H12	120.6
C4—C5—C6	122.6 (3)	C11—C12—C13	118.8 (3)
C6—C5—H5	118.7	C13—C12—H12	120.6
C1—C6—C5	114.5 (3)	C12—C13—H13	119.7
C1—C6—C7	127.9 (3)	C12—C13—C14	120.6 (4)
C5—C6—C7	117.6 (3)	C14—C13—H13	119.7
C6—C7—H7A	109.0	C9—C14—C13	120.8 (3)
C6—C7—H7B	109.0	C9—C14—H14	119.6
C6—C7—C8	112.9 (3)	C13—C14—H14	119.6
H7A—C7—H7B	107.8

Cl1—C3—C4—C5	−178.1 (4)	C4—C5—C6—C1	1.0 (5)
O1—N1—C1—C2	172.2 (3)	C4—C5—C6—C7	−179.7 (3)
O1—N1—C1—C6	−9.1 (5)	C5—C6—C7—C8	−90.9 (4)
O2—N1—C1—C2	−6.8 (5)	C6—C1—C2—C3	1.2 (5)
O2—N1—C1—C6	171.9 (4)	C6—C7—C8—C9	−179.4 (3)
N1—C1—C2—C3	179.9 (3)	C7—C8—C9—C10	84.0 (4)
N1—C1—C6—C5	179.9 (3)	C7—C8—C9—C14	−93.4 (4)
N1—C1—C6—C7	0.7 (5)	C8—C9—C10—C11	−178.7 (3)
C1—C2—C3—Cl1	177.9 (3)	C8—C9—C14—C13	178.5 (3)
C1—C2—C3—C4	−0.4 (5)	C9—C10—C11—C12	1.0 (6)
C1—C2—C3—Cl1A	−176.5 (6)	C10—C9—C14—C13	1.0 (5)
C1—C6—C7—C8	88.3 (4)	C10—C11—C12—C13	−0.5 (6)
C2—C1—C6—C5	−1.4 (4)	C11—C12—C13—C14	0.3 (6)
C2—C1—C6—C7	179.3 (3)	C12—C13—C14—C9	−0.6 (5)
C2—C3—C4—C5	0.0 (6)	C14—C9—C10—C11	−1.2 (5)
C3—C4—C5—C6	−0.3 (6)	Cl1A—C3—C4—C5	176.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.54	3.462 (5)	175

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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

References

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