organic compounds
4-Chloro-2-nitro-1-(2-phenylethyl)benzene
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
In the title compound, C14H12ClNO2, the dihedral angle between the aromatic rings is 6.09 (17)° and the Car—C—C—Car 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.
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.
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).
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 . The Cl atom is disordered over two adjacent sites in a 0.54 (4):0.46 (4) ratio.
details are summarized in Table 2Structural data
CCDC reference: 1543429
https://doi.org/10.1107/S2414314617005478/hb4131sup1.cif
contains datablock I. DOI: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
Data collection: CrystalClear SM Expert (Rigaku, 2011); cell
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).C14H12ClNO2 | Dx = 1.338 Mg m−3 |
Mr = 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 |
Rigaku Saturn724+ diffractometer | Rint = 0.095 |
profile data from ω–scans | θmax = 26.0°, θmin = 3.0° |
Absorption correction: multi-scan (NUMABS; Rigaku, 1999) | h = −17→17 |
Tmin = 0.947, Tmax = 0.960 | k = −9→9 |
13474 measured reflections | l = −16→15 |
2554 independent reflections | 2554 standard reflections |
1389 reflections with I > 2σ(I) |
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(Fo2) + (0.095P)2 + 0.1859P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2554 reflections | Δρmax = 0.18 e Å−3 |
173 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | 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) |
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) |
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) |
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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