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

Tahir, M.N.; Shad, H.A.; Rauf, A.; Khan, A.H.

doi:10.1107/S2056989015001401

organic compounds

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Volume 71| Part 2| February 2015| Pages o137-o138

doi:10.1107/S2056989015001401

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

Muhammad Nawaz Tahir,^a ^* Hazoor Ahmad Shad,^b Abdul Rauf ^c and Abdul Haleem Khan ^d

^aDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, ^cDepartment of Chemistry, Chenab College, Jhang, Punjab, Pakistan, and ^dDrug Controller, Sir Ganga Ram Hospital, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 January 2015; accepted 22 January 2015; online 28 January 2015)

In the title Schiff base, C₁₃H₉Cl₂NO₂, which arose from the condensation of 3,4-dichloroaniline with 2,3-dihydroxybenzaldehyde, the dihedral angle between the aromatic rings is 44.74 (13)°. Intramolecular O—H⋯O and O—H⋯N hydrogen bonds close S(5) and S(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(10) loops. A weak C—H⋯π interaction is also observed.

Keywords: crystal structure; benzene-1,2-diol; Schiff base; hydrogen bonding.

CCDC reference: 1044861

1. Related literature

For related structures, see: Fun et al. (2011 ); Keleşoğlu et al. (2009 ); Shuja et al. (2006 ); Tahir et al. (2012 ); Temel et al. (2007 ).

2. Experimental

2.1. Crystal data

C₁₃H₉Cl₂NO₂
M_r = 282.11
Triclinic, $[P \overline 1]$
a = 6.4237 (8) Å
b = 8.8412 (11) Å
c = 11.7799 (15) Å
α = 88.606 (6)°
β = 76.588 (6)°
γ = 70.193 (5)°
V = 611.20 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 296 K
0.34 × 0.26 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.844, T_max = 0.902
8896 measured reflections
2671 independent reflections
1866 reflections with I > 2σ(I)
R_int = 0.042

2.3. Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.164
S = 1.04
2671 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring (C1–C6).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.89	2.608 (3)	146
O2—H2⋯O1	0.82	2.28	2.729 (3)	115
O2—H2⋯O1ⁱ	0.82	2.20	2.846 (3)	136
C12—H12⋯Cg1ⁱⁱ	0.93	2.83	3.538 (4)	134
Symmetry codes: (i) -x-1, -y+2, -z+1; (ii) x+1, y-1, z.

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: SHELXL97 (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: 1044861

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015001401/hb7353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015001401/hb7353Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015001401/hb7353Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized for forming different metal complexes.

The crystal structures of 2-[(E)-(2,4,6-trichlorophenyl)iminomethyl] phenol (Fun et al., 2011), (E)-3-((2-fluorophenylimino)methyl) benzene-1,2-diol (Temel et al., 2007), (E)-3-[(3-bromophenyl) iminomethyl]benzene-1,2-diol (Kelesoglu et al., 2009), 4-([(E)-2, 3-dihydroxybenzylidene]amino)-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide (Tahir et al., 2012) and 3-(4-bromophenyliminomethyl)benzene-1,2-diol (Shuja et al., 2006) have been published which are related to the title compound due to two moieties of the Schiff base.

In (I) the moieties of 2,3-dihydroxybenzaldehyde A (C1–C7/O1/O2) and 3,4-dichloroanilline B (C8—13/N1/CL1/CL2) are almost planar with r.m.s. deviation of 0.0225 and 0.0172 Å, respectively. The dihedral angle between A/B is 44.219 (50)°. In (I), S(5) and S(6) ring motifs are present due to H-bondings of O—H···O and O—H···N types (Table 1, Fig. 2). The molecules are dimerized due to bifercated H-bonding of O—H···O type (Table 1, Fig. 2). There exist C—H···π (Table 1) and π···π interactions to stablize the dimmers. A π···π interactions between Cg1···Cg1ⁱ [i = -x, 2 - y, 1 - z] at a distance of 3.9101 (15) Å, where Cg1 is centroid of benzene ring (C1—C6) exists. Similarly, there is π···π interactions between Cg2···Cg2ⁱⁱ [il = 1 - x, 1 - y, - z] at a distance of 4.1194 (17) Å, where Cg2 is centroid of benzene ring (C8—C13).

Related literature top

For related structures, see: Fun et al. (2011); Kelesoglu et al. (2009); Shuja et al. (2006); Tahir et al. (2012); Temel et al. (2007).

Experimental top

Equimolar quantities of 3,4-dichloroanilline and 2,3-dihydroxybenzaldehyde were refluxed in methanol for 2 h. The resulting mixture was evaporated to grow crystals. Red prisms were obtained after 48 h.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing (PLATON; Spek, 2009), which shows that molecules form dimers due to O—H···O interactions.

3-{(E)-[(3,4-Dichlorophenyl)imino]methyl}benzene-1,2-diol top

Crystal data top

C₁₃H₉Cl₂NO₂	Z = 2
M_r = 282.11	F(000) = 284
Triclinic, P1	D_x = 1.533 Mg m⁻³
a = 6.4237 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8412 (11) Å	Cell parameters from 1866 reflections
c = 11.7799 (15) Å	θ = 1.8–27.0°
α = 88.606 (6)°	µ = 0.52 mm⁻¹
β = 76.588 (6)°	T = 296 K
γ = 70.193 (5)°	Prism, red
V = 611.20 (13) Å³	0.34 × 0.26 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2671 independent reflections
Radiation source: fine-focus sealed tube	1866 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 7.80 pixels mm^-1	θ_max = 27.0°, θ_min = 1.8°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→9
T_min = 0.844, T_max = 0.902	l = −14→15
8896 measured reflections

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0781P)² + 0.3755P] where P = (F_o² + 2F_c²)/3
2671 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₃H₉Cl₂NO₂	γ = 70.193 (5)°
M_r = 282.11	V = 611.20 (13) Å³
Triclinic, P1	Z = 2
a = 6.4237 (8) Å	Mo Kα radiation
b = 8.8412 (11) Å	µ = 0.52 mm⁻¹
c = 11.7799 (15) Å	T = 296 K
α = 88.606 (6)°	0.34 × 0.26 × 0.20 mm
β = 76.588 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2671 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1866 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.902	R_int = 0.042
8896 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
2671 reflections	Δρ_min = −0.33 e Å⁻³
165 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.24642 (15)	0.26936 (10)	0.01956 (8)	0.0657 (3)
Cl2	0.73742 (15)	0.11968 (10)	0.06575 (9)	0.0707 (3)
O1	−0.2559 (3)	0.9592 (2)	0.38833 (19)	0.0508 (5)
H1	−0.1671	0.8794	0.3473	0.076*
O2	−0.4973 (3)	1.2453 (3)	0.5138 (2)	0.0594 (6)
H2	−0.5353	1.1679	0.5037	0.089*
N1	0.1345 (4)	0.7735 (3)	0.2617 (2)	0.0452 (6)
C1	−0.1526 (5)	1.0707 (3)	0.3887 (2)	0.0388 (6)
C2	−0.2793 (5)	1.2167 (3)	0.4525 (2)	0.0440 (6)
C3	−0.1834 (5)	1.3338 (3)	0.4543 (2)	0.0478 (7)
H3	−0.2694	1.4313	0.4964	0.057*
C4	0.0401 (5)	1.3083 (4)	0.3943 (3)	0.0516 (7)
H4	0.1030	1.3886	0.3954	0.062*
C5	0.1694 (5)	1.1613 (4)	0.3322 (3)	0.0494 (7)
H5	0.3201	1.1427	0.2932	0.059*
C6	0.0738 (5)	1.0419 (3)	0.3285 (2)	0.0409 (6)
C7	0.2124 (5)	0.8875 (3)	0.2674 (2)	0.0440 (6)
H7	0.3638	0.8708	0.2309	0.053*
C8	0.2859 (5)	0.6190 (3)	0.2123 (2)	0.0433 (6)
C9	0.2070 (5)	0.5315 (3)	0.1462 (2)	0.0464 (7)
H9	0.0614	0.5751	0.1334	0.056*
C10	0.3479 (5)	0.3784 (3)	0.0998 (2)	0.0447 (6)
C11	0.5634 (5)	0.3123 (3)	0.1205 (2)	0.0471 (7)
C12	0.6396 (5)	0.3969 (4)	0.1879 (3)	0.0490 (7)
H12	0.7834	0.3514	0.2027	0.059*
C13	0.5000 (5)	0.5513 (3)	0.2339 (2)	0.0480 (7)
H13	0.5511	0.6091	0.2793	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0749 (6)	0.0607 (5)	0.0663 (5)	−0.0278 (4)	−0.0167 (4)	−0.0188 (4)
Cl2	0.0675 (6)	0.0459 (5)	0.0815 (6)	−0.0049 (4)	−0.0040 (4)	−0.0243 (4)
O1	0.0505 (11)	0.0377 (10)	0.0591 (13)	−0.0162 (9)	0.0005 (9)	−0.0157 (9)
O2	0.0502 (12)	0.0463 (12)	0.0765 (15)	−0.0184 (10)	0.0001 (11)	−0.0216 (11)
N1	0.0488 (13)	0.0387 (12)	0.0405 (12)	−0.0089 (10)	−0.0041 (10)	−0.0057 (10)
C1	0.0451 (14)	0.0348 (13)	0.0361 (13)	−0.0133 (11)	−0.0086 (11)	−0.0023 (10)
C2	0.0503 (16)	0.0365 (14)	0.0419 (14)	−0.0111 (12)	−0.0094 (12)	−0.0072 (11)
C3	0.0619 (18)	0.0362 (14)	0.0423 (15)	−0.0117 (13)	−0.0133 (13)	−0.0077 (12)
C4	0.067 (2)	0.0455 (16)	0.0519 (17)	−0.0291 (15)	−0.0173 (15)	0.0016 (13)
C5	0.0536 (17)	0.0495 (16)	0.0469 (16)	−0.0240 (14)	−0.0058 (13)	−0.0009 (13)
C6	0.0489 (15)	0.0346 (13)	0.0355 (13)	−0.0114 (12)	−0.0070 (11)	−0.0001 (11)
C7	0.0473 (15)	0.0405 (14)	0.0372 (14)	−0.0113 (12)	−0.0016 (11)	−0.0053 (11)
C8	0.0508 (16)	0.0365 (14)	0.0359 (14)	−0.0124 (12)	−0.0007 (12)	−0.0059 (11)
C9	0.0490 (16)	0.0435 (15)	0.0442 (15)	−0.0146 (13)	−0.0073 (12)	−0.0045 (12)
C10	0.0531 (16)	0.0436 (15)	0.0373 (14)	−0.0198 (13)	−0.0051 (12)	−0.0047 (11)
C11	0.0524 (16)	0.0396 (14)	0.0406 (15)	−0.0113 (13)	0.0001 (12)	−0.0070 (12)
C12	0.0469 (16)	0.0486 (16)	0.0463 (16)	−0.0102 (13)	−0.0094 (13)	−0.0060 (13)
C13	0.0546 (17)	0.0455 (16)	0.0422 (15)	−0.0160 (13)	−0.0089 (13)	−0.0103 (12)

Geometric parameters (Å, º) top

Cl1—C10	1.733 (3)	C4—H4	0.9300
Cl2—C11	1.731 (3)	C5—C6	1.396 (4)
O1—C1	1.363 (3)	C5—H5	0.9300
O1—H1	0.8200	C6—C7	1.450 (4)
O2—C2	1.359 (3)	C7—H7	0.9300
O2—H2	0.8200	C8—C13	1.383 (4)
N1—C7	1.277 (4)	C8—C9	1.392 (4)
N1—C8	1.423 (3)	C9—C10	1.388 (4)
C1—C2	1.394 (4)	C9—H9	0.9300
C1—C6	1.401 (4)	C10—C11	1.385 (4)
C2—C3	1.375 (4)	C11—C12	1.373 (4)
C3—C4	1.390 (4)	C12—C13	1.394 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.395 (4)	C13—H13	0.9300

C1—O1—H1	109.5	N1—C7—C6	122.5 (3)
C2—O2—H2	109.5	N1—C7—H7	118.7
C7—N1—C8	119.6 (2)	C6—C7—H7	118.7
O1—C1—C2	117.8 (2)	C13—C8—C9	119.9 (2)
O1—C1—C6	122.1 (2)	C13—C8—N1	122.1 (3)
C2—C1—C6	120.1 (2)	C9—C8—N1	117.9 (3)
O2—C2—C3	119.1 (2)	C10—C9—C8	119.3 (3)
O2—C2—C1	120.9 (2)	C10—C9—H9	120.3
C3—C2—C1	120.0 (3)	C8—C9—H9	120.3
C2—C3—C4	120.9 (3)	C11—C10—C9	120.3 (3)
C2—C3—H3	119.6	C11—C10—Cl1	120.7 (2)
C4—C3—H3	119.6	C9—C10—Cl1	118.9 (2)
C3—C4—C5	119.5 (3)	C12—C11—C10	120.5 (3)
C3—C4—H4	120.3	C12—C11—Cl2	118.9 (2)
C5—C4—H4	120.3	C10—C11—Cl2	120.6 (2)
C4—C5—C6	120.3 (3)	C11—C12—C13	119.5 (3)
C4—C5—H5	119.8	C11—C12—H12	120.2
C6—C5—H5	119.8	C13—C12—H12	120.2
C5—C6—C1	119.3 (2)	C8—C13—C12	120.4 (3)
C5—C6—C7	119.8 (3)	C8—C13—H13	119.8
C1—C6—C7	120.9 (2)	C12—C13—H13	119.8

O1—C1—C2—O2	1.1 (4)	C1—C6—C7—N1	2.5 (4)
C6—C1—C2—O2	−178.3 (3)	C7—N1—C8—C13	40.5 (4)
O1—C1—C2—C3	−179.2 (3)	C7—N1—C8—C9	−143.4 (3)
C6—C1—C2—C3	1.4 (4)	C13—C8—C9—C10	−1.9 (4)
O2—C2—C3—C4	179.0 (3)	N1—C8—C9—C10	−178.1 (2)
C1—C2—C3—C4	−0.7 (4)	C8—C9—C10—C11	1.0 (4)
C2—C3—C4—C5	−0.6 (4)	C8—C9—C10—Cl1	179.0 (2)
C3—C4—C5—C6	1.3 (5)	C9—C10—C11—C12	0.5 (4)
C4—C5—C6—C1	−0.7 (4)	Cl1—C10—C11—C12	−177.5 (2)
C4—C5—C6—C7	−177.7 (3)	C9—C10—C11—Cl2	178.5 (2)
O1—C1—C6—C5	179.9 (3)	Cl1—C10—C11—Cl2	0.5 (4)
C2—C1—C6—C5	−0.7 (4)	C10—C11—C12—C13	−1.1 (4)
O1—C1—C6—C7	−3.1 (4)	Cl2—C11—C12—C13	−179.1 (2)
C2—C1—C6—C7	176.3 (3)	C9—C8—C13—C12	1.3 (4)
C8—N1—C7—C6	−172.6 (2)	N1—C8—C13—C12	177.3 (3)
C5—C6—C7—N1	179.5 (3)	C11—C12—C13—C8	0.2 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the benzene ring (C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.608 (3)	146
O2—H2···O1	0.82	2.28	2.729 (3)	115
O2—H2···O1ⁱ	0.82	2.20	2.846 (3)	136
C12—H12···Cg1ⁱⁱ	0.93	2.83	3.538 (4)	134

Symmetry codes: (i) −x−1, −y+2, −z+1; (ii) x+1, y−1, z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the benzene ring (C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.608 (3)	146
O2—H2···O1	0.82	2.28	2.729 (3)	115
O2—H2···O1ⁱ	0.82	2.20	2.846 (3)	136
C12—H12···Cg1ⁱⁱ	0.93	2.83	3.538 (4)	134

Symmetry codes: (i) −x−1, −y+2, −z+1; (ii) x+1, y−1, z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr. Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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