Crystal structure of 1-{(E)-[(3,4-di­chloro­phen­yl)imino]­meth­yl}naphthalen-2-ol

Abstract

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—C_b (b = benzene ring) bond, as indicated by the C=N—C_b—C_b 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 R ₂ ²(16) loops.

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 ▸).

Experimental  

Crystal data  

• C₁₇H₁₁Cl₂NO

• M _r = 316.17

• Monoclinic,

• a = 27.075 (4) Å

• b = 3.9284 (6) Å

• c = 26.359 (4) Å

• β = 95.287 (9)°

• V = 2791.7 (8) ų

• Z = 8

• Mo Kα radiation

• μ = 0.46 mm⁻¹

• T = 296 K

• 0.45 × 0.22 × 0.18 mm

Data collection  

• Bruker Kappa APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T _min = 0.823, T _max = 0.928

• 10968 measured reflections

• 3006 independent reflections

• 1624 reflections with I > 2σ(I)

• R _int = 0.052

Refinement  

• R[F ² > 2σ(F ²)] = 0.049

• wR(F ²) = 0.113

• S = 1.02

• 3006 reflections

• 191 parameters

• H-atom parameters constrained

• Δρ_max = 0.21 e Å⁻³

• Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: 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.

Supplementary Material

CCDC reference: 1420675

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.84	2.565(3)	147
C17H17O1i	0.93	2.60	3.413(3)	147

Symmetry code: (i) .

supplementary crystallographic information

S1. Comment

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.

S2. Experimental

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

S3. Refinement

The H-atoms were positioned geometrically (C–H = 0.93 Å, O–H = 0.82 Å) and refined as riding with U_iso(H) = xU_eq(C, O), where x = 1.5 for hydroxy and x = 1.2 for other H-atoms.

Figures

Fig. 1.

View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line indicates the intramolecular H-bond interaction.

Fig. 2.

Inversion dimers in the crystal of the title compound.

Crystal data

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

Data collection

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

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

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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.