organic compounds
E)-[(3,4-dichlorophenyl)imino]methyl}naphthalen-2-ol
of 1-{(aDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan, and bDepartment of Chemistry, University of Sargodha, Sargodha, Punjab, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C17H11Cl2NO, the dihedral angle between the planes of the naphthalene ring system and the benzene ring is 28.88 (11)°. The main twist in the molecule occurs about the N—Cb (b = benzene ring) bond, as indicated by the C=N—Cb—Cb torsion angle of 31.0 (4)°. An intramolecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of very weak C—H⋯O interactions generate R22(16) loops.
Keywords: crystal structure; naphthalen-2-ol; inversion dimers; hydrogen bonding.
CCDC reference: 1420675
1. Related literature
For related structures, see: Elmali et al. (1998); Pavlovic et al. (2002); Pierens et al. (2012); Yıldız et al. (2006); Wang et al. (2011).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.
Supporting information
CCDC reference: 1420675
https://doi.org/10.1107/S2056989015015959/hb7492sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015015959/hb7492Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015959/hb7492Isup3.cml
Equimolar quantities of 3,4-dichloroaniline and 2-hydroxynaphthaldehyde were refluxed in methanol for 2 h. The solution was kept at room temperature for crystallization which afforded yellow needles after 2 h.
Melting point: 375 K
The H-atoms were positioned geometrically (C–H = 0.93 Å, O–H = 0.82 Å) and refined as riding with Uiso(H) = xUeq(C, O), where x = 1.5 for hydroxy and x = 1.2 for other H-atoms.
The crystal structures of (E)-1-[(2-chloro-4-nitrophenylimino)methyl]naphthalen-2-ol (Wang et al., 2011), N-(3-chlorophenyl)-2-hydroxy-1-naphthaldimine (Pavlovic et al., 2002), N-(2-hydroxy-1-naphthylmethylene)-2,5-dichloroaniline (Yildiz et al., 2006), 1-(((4-chlorophenyl)imino)methyl)-2-naphthol (Pierens et al., 2002) and N-(3,5-dichlorophenyl)naphthaldimine (Elmali et al., 1998) have been published which are related to the title compound (I, Fig. 1).
In (I), the parts of 2-hydroxynaphthaldehyde A (C1–C11/O1) and B (N1/C12–C17/CL1/CL2) of 3,4-dichloraniline are planar with r. m. s. deviation of 0.0084 Å and 0.0111 Å, respectively. The dihedral angle between A/B is 29.00 (5)°. There exists S (6) ring motif due to intramolecular H-interaction of O–H···N type. The molecules are stabilized in the form of dimmers (Table 1, Fig. 2) due to C–H···O and O–H···N types of interactions and complete R44(12) ring motif.
For related structures, see: Elmali et al. (1998); Pavlovic et al. (2002); Pierens et al. (2012); Yildiz et al. (2006); Wang et al. (2011).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C17H11Cl2NO | F(000) = 1296 |
Mr = 316.17 | Dx = 1.502 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.075 (4) Å | Cell parameters from 1624 reflections |
b = 3.9284 (6) Å | θ = 2.3–27.0° |
c = 26.359 (4) Å | µ = 0.46 mm−1 |
β = 95.287 (9)° | T = 296 K |
V = 2791.7 (8) Å3 | Needle, yellow |
Z = 8 | 0.45 × 0.22 × 0.18 mm |
Bruker Kappa APEXII CCD diffractometer | 3006 independent reflections |
Radiation source: fine-focus sealed tube | 1624 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 7.70 pixels mm-1 | θmax = 27.0°, θmin = 2.3° |
ω scans | h = −34→34 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −3→5 |
Tmin = 0.823, Tmax = 0.928 | l = −33→24 |
10968 measured reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.8217P] where P = (Fo2 + 2Fc2)/3 |
3006 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C17H11Cl2NO | V = 2791.7 (8) Å3 |
Mr = 316.17 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 27.075 (4) Å | µ = 0.46 mm−1 |
b = 3.9284 (6) Å | T = 296 K |
c = 26.359 (4) Å | 0.45 × 0.22 × 0.18 mm |
β = 95.287 (9)° |
Bruker Kappa APEXII CCD diffractometer | 3006 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1624 reflections with I > 2σ(I) |
Tmin = 0.823, Tmax = 0.928 | Rint = 0.052 |
10968 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.21 e Å−3 |
3006 reflections | Δρmin = −0.29 e Å−3 |
191 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.01545 (2) | 0.1563 (2) | −0.07226 (3) | 0.0583 (3) | |
Cl2 | 0.03878 (3) | −0.1601 (2) | −0.16134 (3) | 0.0657 (3) | |
O1 | 0.23523 (6) | 0.7303 (6) | 0.05438 (8) | 0.0661 (6) | |
H1 | 0.2167 | 0.6298 | 0.0331 | 0.099* | |
N1 | 0.15606 (7) | 0.4249 (6) | 0.01785 (9) | 0.0480 (6) | |
C1 | 0.21559 (9) | 0.7303 (7) | 0.09872 (11) | 0.0473 (7) | |
C2 | 0.24423 (10) | 0.8780 (8) | 0.14042 (12) | 0.0550 (8) | |
H2 | 0.2753 | 0.9668 | 0.1359 | 0.066* | |
C3 | 0.22719 (10) | 0.8919 (7) | 0.18642 (12) | 0.0514 (8) | |
H3 | 0.2467 | 0.9929 | 0.2132 | 0.062* | |
C4 | 0.18026 (9) | 0.7570 (7) | 0.19561 (10) | 0.0434 (7) | |
C5 | 0.16273 (10) | 0.7752 (7) | 0.24400 (11) | 0.0510 (8) | |
H5 | 0.1823 | 0.8789 | 0.2705 | 0.061* | |
C6 | 0.11812 (11) | 0.6459 (8) | 0.25307 (11) | 0.0568 (8) | |
H6 | 0.1071 | 0.6605 | 0.2854 | 0.068* | |
C7 | 0.08905 (10) | 0.4908 (8) | 0.21345 (11) | 0.0555 (8) | |
H7 | 0.0584 | 0.3998 | 0.2195 | 0.067* | |
C8 | 0.10470 (9) | 0.4700 (7) | 0.16588 (11) | 0.0465 (7) | |
H8 | 0.0844 | 0.3658 | 0.1401 | 0.056* | |
C9 | 0.15082 (8) | 0.6018 (6) | 0.15477 (10) | 0.0380 (7) | |
C10 | 0.16918 (9) | 0.5897 (7) | 0.10521 (10) | 0.0407 (7) | |
C11 | 0.14109 (9) | 0.4337 (7) | 0.06279 (11) | 0.0446 (7) | |
H11 | 0.1108 | 0.3346 | 0.0679 | 0.053* | |
C12 | 0.12664 (9) | 0.2802 (7) | −0.02362 (10) | 0.0427 (7) | |
C13 | 0.07522 (9) | 0.2847 (6) | −0.02738 (10) | 0.0396 (6) | |
H13 | 0.0587 | 0.3810 | −0.0015 | 0.047* | |
C14 | 0.04871 (9) | 0.1476 (7) | −0.06919 (10) | 0.0390 (6) | |
C15 | 0.07202 (10) | 0.0081 (7) | −0.10842 (10) | 0.0438 (7) | |
C16 | 0.12334 (10) | 0.0042 (8) | −0.10466 (11) | 0.0516 (8) | |
H16 | 0.1397 | −0.0916 | −0.1307 | 0.062* | |
C17 | 0.15025 (10) | 0.1399 (8) | −0.06306 (11) | 0.0518 (8) | |
H17 | 0.1847 | 0.1378 | −0.0612 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0427 (4) | 0.0719 (6) | 0.0601 (5) | 0.0001 (4) | 0.0043 (3) | −0.0098 (4) |
Cl2 | 0.0811 (5) | 0.0691 (6) | 0.0472 (5) | −0.0065 (4) | 0.0076 (4) | −0.0140 (4) |
O1 | 0.0435 (11) | 0.0918 (19) | 0.0632 (14) | −0.0072 (11) | 0.0063 (10) | 0.0031 (13) |
N1 | 0.0398 (12) | 0.0571 (17) | 0.0472 (15) | 0.0038 (11) | 0.0049 (11) | 0.0025 (13) |
C1 | 0.0393 (15) | 0.049 (2) | 0.0532 (19) | 0.0037 (13) | 0.0036 (13) | 0.0074 (15) |
C2 | 0.0361 (15) | 0.057 (2) | 0.071 (2) | −0.0060 (13) | −0.0020 (15) | 0.0009 (18) |
C3 | 0.0463 (16) | 0.045 (2) | 0.060 (2) | −0.0006 (14) | −0.0104 (14) | 0.0006 (16) |
C4 | 0.0414 (15) | 0.0388 (18) | 0.0484 (18) | 0.0069 (13) | −0.0041 (13) | 0.0052 (14) |
C5 | 0.0538 (17) | 0.047 (2) | 0.0503 (19) | 0.0084 (14) | −0.0075 (14) | −0.0064 (15) |
C6 | 0.0611 (19) | 0.060 (2) | 0.0496 (19) | 0.0070 (16) | 0.0051 (15) | −0.0012 (17) |
C7 | 0.0479 (17) | 0.066 (2) | 0.053 (2) | −0.0032 (15) | 0.0066 (14) | 0.0050 (18) |
C8 | 0.0422 (15) | 0.0476 (19) | 0.0476 (18) | −0.0022 (13) | −0.0066 (12) | 0.0022 (15) |
C9 | 0.0345 (13) | 0.0361 (17) | 0.0421 (16) | 0.0040 (12) | −0.0038 (11) | 0.0055 (13) |
C10 | 0.0354 (14) | 0.0375 (17) | 0.0479 (17) | 0.0024 (12) | −0.0036 (12) | 0.0062 (14) |
C11 | 0.0390 (14) | 0.0464 (19) | 0.0481 (18) | 0.0039 (13) | 0.0025 (13) | 0.0075 (15) |
C12 | 0.0441 (15) | 0.0440 (18) | 0.0403 (16) | 0.0047 (13) | 0.0052 (12) | 0.0048 (14) |
C13 | 0.0406 (14) | 0.0441 (17) | 0.0350 (15) | 0.0064 (13) | 0.0089 (11) | 0.0011 (14) |
C14 | 0.0418 (14) | 0.0368 (17) | 0.0393 (16) | 0.0030 (12) | 0.0083 (12) | 0.0059 (14) |
C15 | 0.0564 (17) | 0.0380 (17) | 0.0376 (16) | 0.0009 (14) | 0.0070 (13) | 0.0036 (14) |
C16 | 0.0600 (19) | 0.054 (2) | 0.0432 (17) | 0.0122 (15) | 0.0178 (14) | −0.0008 (16) |
C17 | 0.0416 (15) | 0.065 (2) | 0.0500 (18) | 0.0084 (15) | 0.0118 (14) | 0.0066 (17) |
Cl1—C14 | 1.732 (2) | C6—H6 | 0.9300 |
Cl2—C15 | 1.721 (3) | C7—C8 | 1.363 (4) |
O1—C1 | 1.328 (3) | C7—H7 | 0.9300 |
O1—H1 | 0.8200 | C8—C9 | 1.407 (3) |
N1—C11 | 1.287 (3) | C8—H8 | 0.9300 |
N1—C12 | 1.411 (3) | C9—C10 | 1.441 (3) |
C1—C10 | 1.397 (3) | C10—C11 | 1.431 (3) |
C1—C2 | 1.410 (4) | C11—H11 | 0.9300 |
C2—C3 | 1.338 (4) | C12—C17 | 1.384 (4) |
C2—H2 | 0.9300 | C12—C13 | 1.387 (3) |
C3—C4 | 1.418 (4) | C13—C14 | 1.369 (3) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.403 (4) | C14—C15 | 1.374 (3) |
C4—C9 | 1.417 (3) | C15—C16 | 1.384 (4) |
C5—C6 | 1.352 (4) | C16—C17 | 1.367 (4) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—C7 | 1.389 (4) | C17—H17 | 0.9300 |
C1—O1—H1 | 109.5 | C8—C9—C10 | 124.3 (2) |
C11—N1—C12 | 121.4 (2) | C4—C9—C10 | 119.1 (2) |
O1—C1—C10 | 123.0 (3) | C1—C10—C11 | 119.5 (3) |
O1—C1—C2 | 116.7 (2) | C1—C10—C9 | 119.2 (2) |
C10—C1—C2 | 120.2 (3) | C11—C10—C9 | 121.3 (2) |
C3—C2—C1 | 120.8 (3) | N1—C11—C10 | 122.7 (2) |
C3—C2—H2 | 119.6 | N1—C11—H11 | 118.6 |
C1—C2—H2 | 119.6 | C10—C11—H11 | 118.6 |
C2—C3—C4 | 121.9 (3) | C17—C12—C13 | 118.8 (2) |
C2—C3—H3 | 119.0 | C17—C12—N1 | 118.4 (2) |
C4—C3—H3 | 119.0 | C13—C12—N1 | 122.8 (2) |
C5—C4—C9 | 119.9 (2) | C14—C13—C12 | 120.1 (2) |
C5—C4—C3 | 121.3 (3) | C14—C13—H13 | 120.0 |
C9—C4—C3 | 118.8 (3) | C12—C13—H13 | 120.0 |
C6—C5—C4 | 121.6 (3) | C13—C14—C15 | 121.3 (2) |
C6—C5—H5 | 119.2 | C13—C14—Cl1 | 118.6 (2) |
C4—C5—H5 | 119.2 | C15—C14—Cl1 | 120.1 (2) |
C5—C6—C7 | 119.1 (3) | C14—C15—C16 | 118.6 (2) |
C5—C6—H6 | 120.5 | C14—C15—Cl2 | 121.4 (2) |
C7—C6—H6 | 120.5 | C16—C15—Cl2 | 120.0 (2) |
C8—C7—C6 | 121.0 (3) | C17—C16—C15 | 120.7 (3) |
C8—C7—H7 | 119.5 | C17—C16—H16 | 119.7 |
C6—C7—H7 | 119.5 | C15—C16—H16 | 119.7 |
C7—C8—C9 | 121.8 (3) | C16—C17—C12 | 120.6 (2) |
C7—C8—H8 | 119.1 | C16—C17—H17 | 119.7 |
C9—C8—H8 | 119.1 | C12—C17—H17 | 119.7 |
C8—C9—C4 | 116.6 (2) | ||
O1—C1—C2—C3 | 179.4 (3) | C4—C9—C10—C1 | 0.2 (4) |
C10—C1—C2—C3 | −1.3 (4) | C8—C9—C10—C11 | −0.8 (4) |
C1—C2—C3—C4 | 0.7 (4) | C4—C9—C10—C11 | 179.5 (2) |
C2—C3—C4—C5 | −179.6 (3) | C12—N1—C11—C10 | −177.6 (2) |
C2—C3—C4—C9 | 0.3 (4) | C1—C10—C11—N1 | −2.1 (4) |
C9—C4—C5—C6 | 0.4 (4) | C9—C10—C11—N1 | 178.6 (2) |
C3—C4—C5—C6 | −179.7 (3) | C11—N1—C12—C17 | −151.6 (3) |
C4—C5—C6—C7 | 0.1 (4) | C11—N1—C12—C13 | 31.0 (4) |
C5—C6—C7—C8 | −0.5 (4) | C17—C12—C13—C14 | 0.9 (4) |
C6—C7—C8—C9 | 0.3 (4) | N1—C12—C13—C14 | 178.4 (2) |
C7—C8—C9—C4 | 0.1 (4) | C12—C13—C14—C15 | −1.0 (4) |
C7—C8—C9—C10 | −179.5 (3) | C12—C13—C14—Cl1 | 179.7 (2) |
C5—C4—C9—C8 | −0.5 (4) | C13—C14—C15—C16 | 0.9 (4) |
C3—C4—C9—C8 | 179.6 (2) | Cl1—C14—C15—C16 | −179.8 (2) |
C5—C4—C9—C10 | 179.2 (2) | C13—C14—C15—Cl2 | −179.3 (2) |
C3—C4—C9—C10 | −0.7 (4) | Cl1—C14—C15—Cl2 | 0.1 (3) |
O1—C1—C10—C11 | 0.7 (4) | C14—C15—C16—C17 | −0.7 (4) |
C2—C1—C10—C11 | −178.5 (3) | Cl2—C15—C16—C17 | 179.4 (2) |
O1—C1—C10—C9 | −179.9 (2) | C15—C16—C17—C12 | 0.8 (5) |
C2—C1—C10—C9 | 0.8 (4) | C13—C12—C17—C16 | −0.8 (4) |
C8—C9—C10—C1 | 179.8 (2) | N1—C12—C17—C16 | −178.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.84 | 2.565 (3) | 147 |
C17—H17···O1i | 0.93 | 2.60 | 3.413 (3) | 147 |
Symmetry code: (i) −x+1/2, −y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.84 | 2.565 (3) | 147 |
C17—H17···O1i | 0.93 | 2.60 | 3.413 (3) | 147 |
Symmetry code: (i) −x+1/2, −y+1/2, −z. |
Acknowledgements
The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.
References
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The crystal structures of (E)-1-[(2-chloro-4-nitrophenylimino)methyl]naphthalen-2-ol (Wang et al., 2011), N-(3-chlorophenyl)-2-hydroxy-1-naphthaldimine (Pavlovic et al., 2002), N-(2-hydroxy-1-naphthylmethylene)-2,5-dichloroaniline (Yildiz et al., 2006), 1-(((4-chlorophenyl)imino)methyl)-2-naphthol (Pierens et al., 2002) and N-(3,5-dichlorophenyl)naphthaldimine (Elmali et al., 1998) have been published which are related to the title compound (I, Fig. 1).
In (I), the parts of 2-hydroxynaphthaldehyde A (C1–C11/O1) and B (N1/C12–C17/CL1/CL2) of 3,4-dichloraniline are planar with r. m. s. deviation of 0.0084 Å and 0.0111 Å, respectively. The dihedral angle between A/B is 29.00 (5)°. There exists S (6) ring motif due to intramolecular H-interaction of O–H···N type. The molecules are stabilized in the form of dimmers (Table 1, Fig. 2) due to C–H···O and O–H···N types of interactions and complete R44(12) ring motif.