6,6′-Dimeth­oxy-2,2′-[(E,E′)-(4-chloro-m-phenyl­ene)bis­(nitrilo­methyl­idyne)]diphenol

Yamin, B.M.; Bakar, S.N.A.; Kassim, K.; Bahron, H.

doi:10.1107/S1600536809037386

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2573

doi:10.1107/S1600536809037386

Open

access

6,6′-Dimethoxy-2,2′-[(E,E′)-(4-chloro-m-phenylene)bis(nitrilomethylidyne)]diphenol

Bohari M. Yamin,^a Siti Najihah A. Bakar,^b Karimah Kassim ^b and Hadariah Bahron ^b ^*

^aSchool of Chemical Sciences and Food Technology, Univeriti Kebangsaan Malaysia, UKM 43500 Bangi Selangor. Malaysia, and ^bDepartment of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
^*Correspondence e-mail: hadariah@salam.uitm.edu.my

(Received 4 September 2009; accepted 15 September 2009; online 30 September 2009)

The title compound, C₂₂H₁₉ClN₂O₄, has the appearance of a warped butterfly. One 2-hydroxy-3-methoxybenzylideneamino fragment is planar [with a maximum deviation of 0.056 (3) Å] and forms a dihedral angle of 9.85 (9)° with the central benzene ring. The other fragment is not planar; however, the methoxyphenol group is planar [with the maximum deviation of 0.033 (2) Å] and makes a dihedral angle of 41.7 (3)° with the central benzene ring. The molecule is stabilized by intramolecular O—H⋯N hydrogen bonding. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonding and C—H⋯π interactions.

Related literature

For the biological activity of Schiff bases, see: Aranha et al. (2007 ) and for the corrosion inhibition potential of Schiff bases, see: Chetouani et al. (2005 ). For related structures, see: Hernández-Molina et al. (1997 ); Torayama et al. (1997 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₉ClN₂O₄
M_r = 410.84
Monoclinic, P 2₁ /n
a = 9.900 (2) Å
b = 6.8589 (12) Å
c = 28.830 (6) Å
β = 94.659 (4)°
V = 1951.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.41 × 0.40 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.912, T_max = 0.975
12204 measured reflections
4049 independent reflections
2758 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.131
S = 1.06
4049 reflections
272 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.83 (3)	1.81 (3)	2.586 (3)	155 (3)
O4—H4⋯N2	0.82 (3)	1.86 (3)	2.588 (3)	148 (3)
C11—H11⋯O4ⁱ	0.93	2.59	3.392 (3)	145
C3—H3⋯Cg3ⁱⁱ	0.93	2.89	3.635 (3)	138
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x, y+1, z. Cg3 is the centroid of the C16–C21 ring.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037386/dn2481sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037386/dn2481Isup2.hkl

checkCIF report

Comment top

Continous studies on Schiff bases are driven by their biological activities such as antimicrobial (Aranha et al., 2007) and chemical properties such as corrosion inhibition (Chetouani et al., 2005). Some m-phenylenediamine derived Schiff bases such as N,N'-disalicylidene-1,3-diiminobenzene and their complexes have been reported (Hernández-Molina et al., 1997; Torayama et al., 1997). The present compound is also a m-phenylenediamine derived Schiff base but with a chloro substituent at the ortho position. The Schiff base groups that attached to the 1,3-positions are 2-iminomethyl-6-methoxyphenols (Fig.1).

The whole molecule appears like a warped butterfly. The 2-imino methyl-6-methoxyphenol right wing N1/C7—C14)/O1/O2 is planar with a maximum deviation of 0.056 (3)Å for C14 atom from the least square plane. However, the left wing is twisted with the C15—N2—C4—C3 torsion angle of 41.7 (3)° compared to 9.1 (3)°. for the C7—N1—C6—C5 torsion angle of the right wing. The methoxyphenol O3/O4/(C16—C22) fragment of the left wing is planar with the maximum deviation of 0.033 (2)Å for C20 atom. As a result, the methoxyphenol groups are in opposite orientation. The central (C1—C6) benzene ring makes dihedral angle of 9.85 (9)Å with the right N1/C7—C14)/O1/O1 wing and 44.25 (9)° with the O3/O4/(C16—C22) methoxyphenol fragment. The dihedral angle between the right wing and the methoxyphenol fragment is 53.17 (7)°. The bond lengths and angles are in normal ranges (Allen et al., 1987).

There are two O—H···N intramolecular hydrogen bonds (Table 1). In the crystal structure, the molecule is stabilized by weak C—H···O intermolecular hydrogen bonds, C—H···π interaction (Tables 1) and van der Waal forces.

Related literature top

For the biological activity of Schiff bases, see: Aranha et al. (2007); Chetouani et al. (2005). For related structures, see: Hernández-Molina et al. (1997); Torayama et al. (1997). For bond-length data, see: Allen et al. (1987). Cg3 is the centroid of the C16–C21 ring.

Experimental top

The compound was synthesized by refluxing 1,3-diamino-4-chlorobenzene (0.428 g, 3 mmol) with 3-methoxysalicylaldehyde (0.912 g, 6 mmol) in ethanol for 24 h. The precipitate obtained was filtered off, washed with ethanol and dried in-vacuo. It was recrystallized from a mixed solvent of chloroform and ethanol (1:1) to afford brownish yellow single crystals. Yield 92%. Melting point 468–470 K. Analytical calculation for C₂₂H₁₉ClN₂O₄ [Cl-mpd(o-van)₂]: C, 64.31; H, 4.66; N, 6.82. Found: C, 64.18; H, 4.65; N, 6.93. IR (cm^-1): ν(C=N) 1611.7 (m), ν(C—O—C) 1253.9 (s), ν(C—OH) 1212.7 (w), ν(C—Cl) 1099.8 (w). ¹H NMR (CDCl₃, 300 MHz, p.p.m.): δ = 13.5002 (1H, s, OH), 13.2536 (1H, s, OH), 8.737 (1H, s, HC=N), 8.684 (1H, s, HC=N), 7.220–6.935)(9H, m, H-aromatic), 3.977 (3H, s, OCH₃), 3.969 (3H, s, OCH₃).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of compound, (1), with displacement ellipsoid drawn at the 50% probablity level. H atoms are represented as small sphere of arbitrary radii.

6,6'-Dimethoxy-2,2'-[(E,E')-(4-chloro-m- phenylene)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₂H₁₉ClN₂O₄	F(000) = 856
M_r = 410.84	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 468.0–470.0 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.900 (2) Å	Cell parameters from 2429 reflections
b = 6.8589 (12) Å	θ = 1.4–26.5°
c = 28.830 (6) Å	µ = 0.23 mm⁻¹
β = 94.659 (4)°	T = 298 K
V = 1951.2 (7) Å³	Block, yellow
Z = 4	0.41 × 0.40 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4049 independent reflections
Radiation source: fine-focus sealed tube	2758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 83.66 pixels mm^-1	θ_max = 26.5°, θ_min = 1.4°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −8→7
T_min = 0.912, T_max = 0.975	l = −29→36
12204 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0536P)² + 0.4146P] where P = (F_o² + 2F_c²)/3
4049 reflections	(Δ/σ)_max = 0.002
272 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₁₉ClN₂O₄	V = 1951.2 (7) Å³
M_r = 410.84	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.900 (2) Å	µ = 0.23 mm⁻¹
b = 6.8589 (12) Å	T = 298 K
c = 28.830 (6) Å	0.41 × 0.40 × 0.11 mm
β = 94.659 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4049 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2758 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.975	R_int = 0.030
12204 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	2 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.21 e Å⁻³
4049 reflections	Δρ_min = −0.17 e Å⁻³
272 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
O1	0.4334 (2)	0.6076 (3)	1.14002 (7)	0.0751 (5)
O2	0.5923 (2)	0.6402 (2)	1.07204 (7)	0.0671 (5)
O3	0.90619 (18)	−0.3720 (3)	0.77614 (6)	0.0682 (5)
O4	0.86271 (17)	−0.0603 (3)	0.82460 (7)	0.0655 (5)
Cl1	0.83872 (7)	0.86091 (8)	1.00563 (2)	0.0658 (2)
N2	0.9571 (2)	0.2143 (3)	0.87964 (6)	0.0560 (5)
N1	0.71450 (19)	0.4773 (2)	1.00623 (7)	0.0496 (5)
C5	0.8366 (2)	0.3491 (3)	0.94045 (8)	0.0523 (6)
H5	0.7886	0.2325	0.9402	0.063*
C6	0.8069 (2)	0.4937 (3)	0.97170 (8)	0.0470 (5)
C1	0.8754 (2)	0.6715 (3)	0.96890 (8)	0.0497 (6)
C2	0.9714 (3)	0.6982 (3)	0.93761 (8)	0.0594 (7)
H2A	1.0153	0.8177	0.9363	0.071*
C3	1.0032 (3)	0.5503 (4)	0.90814 (8)	0.0602 (7)
H3	1.0695	0.5683	0.8874	0.072*
C4	0.9347 (2)	0.3727 (3)	0.90976 (8)	0.0519 (6)
C7	0.6600 (2)	0.3163 (3)	1.01624 (8)	0.0509 (6)
H7	0.6779	0.2059	0.9990	0.061*
C8	0.5717 (2)	0.2992 (3)	1.05322 (8)	0.0474 (5)
C9	0.5173 (3)	0.1175 (3)	1.06386 (9)	0.0572 (6)
H9	0.5382	0.0082	1.0468	0.069*
C10	0.4341 (3)	0.0992 (3)	1.09897 (10)	0.0633 (7)
H10	0.3987	−0.0222	1.1057	0.076*
C11	0.4019 (2)	0.2612 (4)	1.12488 (9)	0.0590 (6)
H11	0.3432	0.2482	1.1483	0.071*
C12	0.4565 (2)	0.4408 (3)	1.11604 (8)	0.0542 (6)
C13	0.5416 (2)	0.4621 (3)	1.08000 (8)	0.0491 (6)
C15	1.0764 (3)	0.1673 (4)	0.86971 (8)	0.0591 (6)
H15	1.1497	0.2411	0.8819	0.071*
C16	1.1010 (2)	0.0026 (4)	0.84010 (8)	0.0549 (6)
C17	1.2336 (3)	−0.0564 (5)	0.83404 (10)	0.0728 (8)
H17	1.3061	0.0163	0.8473	0.087*
C18	1.2577 (3)	−0.2191 (5)	0.80892 (10)	0.0788 (8)
H18	1.3463	−0.2582	0.8056	0.095*
C19	1.1499 (3)	−0.3269 (4)	0.78828 (9)	0.0687 (7)
H19	1.1673	−0.4366	0.7708	0.082*
C20	1.0186 (2)	−0.2735 (4)	0.79340 (8)	0.0549 (6)
C21	0.9926 (2)	−0.1070 (4)	0.81969 (8)	0.0521 (6)
C14	0.3549 (3)	0.5911 (5)	1.17851 (11)	0.0893 (9)
H14A	0.2687	0.5341	1.1687	0.134*
H14B	0.3412	0.7181	1.1913	0.134*
H14C	0.4013	0.5098	1.2018	0.134*
C22	0.9258 (3)	−0.5492 (4)	0.75161 (11)	0.0839 (9)
H22A	0.9725	−0.5221	0.7244	0.126*
H22B	0.8394	−0.6070	0.7425	0.126*
H22C	0.9787	−0.6377	0.7714	0.126*
H4	0.861 (3)	0.027 (4)	0.8438 (9)	0.102 (12)*
H2	0.643 (3)	0.620 (5)	1.0511 (9)	0.110 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0940 (14)	0.0583 (11)	0.0763 (12)	0.0002 (9)	0.0263 (11)	−0.0095 (9)
O2	0.0916 (14)	0.0332 (9)	0.0793 (13)	−0.0106 (9)	0.0236 (11)	−0.0061 (8)
O3	0.0633 (11)	0.0731 (12)	0.0684 (11)	−0.0013 (9)	0.0056 (9)	−0.0191 (9)
O4	0.0494 (11)	0.0733 (12)	0.0736 (12)	−0.0005 (9)	0.0040 (9)	−0.0192 (10)
Cl1	0.0819 (5)	0.0395 (3)	0.0753 (4)	−0.0074 (3)	0.0026 (3)	−0.0034 (3)
N2	0.0637 (14)	0.0580 (12)	0.0462 (11)	−0.0071 (10)	0.0044 (10)	−0.0001 (10)
N1	0.0562 (12)	0.0357 (10)	0.0563 (11)	−0.0062 (8)	0.0013 (10)	0.0008 (8)
C5	0.0593 (15)	0.0426 (12)	0.0538 (13)	−0.0104 (11)	−0.0028 (12)	0.0013 (11)
C6	0.0521 (14)	0.0405 (12)	0.0471 (13)	−0.0022 (10)	−0.0045 (11)	0.0041 (10)
C1	0.0610 (15)	0.0372 (12)	0.0490 (13)	−0.0042 (10)	−0.0064 (11)	0.0058 (10)
C2	0.0772 (17)	0.0457 (13)	0.0542 (14)	−0.0173 (12)	−0.0012 (13)	0.0103 (12)
C3	0.0732 (17)	0.0589 (15)	0.0488 (14)	−0.0128 (13)	0.0062 (12)	0.0096 (12)
C4	0.0626 (15)	0.0505 (13)	0.0419 (12)	−0.0081 (11)	−0.0005 (11)	0.0032 (11)
C7	0.0577 (14)	0.0345 (12)	0.0599 (14)	0.0004 (10)	0.0015 (12)	−0.0025 (10)
C8	0.0480 (13)	0.0359 (11)	0.0572 (14)	−0.0027 (9)	−0.0013 (11)	0.0029 (10)
C9	0.0669 (16)	0.0373 (12)	0.0669 (16)	−0.0074 (11)	0.0029 (13)	0.0001 (11)
C10	0.0705 (18)	0.0450 (14)	0.0734 (17)	−0.0167 (12)	−0.0005 (14)	0.0080 (12)
C11	0.0537 (15)	0.0626 (16)	0.0606 (15)	−0.0073 (12)	0.0044 (12)	0.0092 (13)
C12	0.0563 (15)	0.0475 (13)	0.0581 (15)	0.0012 (11)	0.0008 (12)	−0.0016 (12)
C13	0.0527 (14)	0.0352 (12)	0.0586 (14)	−0.0027 (10)	0.0001 (12)	0.0020 (10)
C15	0.0621 (17)	0.0682 (16)	0.0466 (13)	−0.0132 (13)	0.0011 (12)	0.0046 (12)
C16	0.0527 (15)	0.0685 (16)	0.0436 (13)	−0.0057 (12)	0.0045 (11)	0.0049 (12)
C17	0.0521 (17)	0.099 (2)	0.0667 (17)	−0.0091 (15)	0.0034 (14)	−0.0022 (17)
C18	0.0530 (17)	0.108 (2)	0.0767 (19)	0.0087 (16)	0.0120 (15)	−0.0070 (19)
C19	0.0680 (18)	0.0807 (19)	0.0584 (16)	0.0079 (15)	0.0111 (14)	−0.0029 (14)
C20	0.0537 (15)	0.0703 (16)	0.0409 (12)	0.0011 (13)	0.0057 (11)	0.0028 (12)
C21	0.0479 (14)	0.0653 (15)	0.0433 (12)	0.0004 (12)	0.0057 (11)	0.0039 (11)
C14	0.101 (2)	0.092 (2)	0.078 (2)	0.0127 (19)	0.0249 (18)	−0.0081 (17)
C22	0.089 (2)	0.080 (2)	0.082 (2)	0.0068 (17)	−0.0002 (17)	−0.0270 (17)

Geometric parameters (Å, º) top

O1—C12	1.366 (3)	C8—C13	1.403 (3)
O1—C14	1.410 (3)	C9—C10	1.361 (4)
O2—C13	1.348 (3)	C9—H9	0.9300
O2—H2	0.83 (3)	C10—C11	1.390 (4)
O3—C20	1.361 (3)	C10—H10	0.9300
O3—C22	1.427 (3)	C11—C12	1.378 (3)
O4—C21	1.343 (3)	C11—H11	0.9300
O4—H4	0.82 (2)	C12—C13	1.397 (3)
Cl1—C1	1.733 (2)	C15—C16	1.448 (3)
N2—C15	1.279 (3)	C15—H15	0.9300
N2—C4	1.419 (3)	C16—C17	1.398 (4)
N1—C7	1.273 (3)	C16—C21	1.401 (3)
N1—C6	1.410 (3)	C17—C18	1.362 (4)
C5—C4	1.376 (3)	C17—H17	0.9300
C5—C6	1.388 (3)	C18—C19	1.391 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—C1	1.401 (3)	C19—C20	1.370 (4)
C1—C2	1.375 (3)	C19—H19	0.9300
C2—C3	1.377 (3)	C20—C21	1.406 (3)
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.397 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C7—C8	1.438 (3)	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—C9	1.402 (3)	C22—H22C	0.9600

C12—O1—C14	117.2 (2)	O1—C12—C11	124.8 (2)
C13—O2—H2	103 (2)	O1—C12—C13	115.1 (2)
C20—O3—C22	117.6 (2)	C11—C12—C13	120.0 (2)
C21—O4—H4	109 (2)	O2—C13—C12	118.4 (2)
C15—N2—C4	121.5 (2)	O2—C13—C8	122.0 (2)
C7—N1—C6	122.7 (2)	C12—C13—C8	119.6 (2)
C4—C5—C6	122.1 (2)	N2—C15—C16	122.1 (2)
C4—C5—H5	119.0	N2—C15—H15	119.0
C6—C5—H5	119.0	C16—C15—H15	119.0
C5—C6—C1	117.1 (2)	C17—C16—C21	119.2 (2)
C5—C6—N1	125.8 (2)	C17—C16—C15	120.3 (2)
C1—C6—N1	117.1 (2)	C21—C16—C15	120.4 (2)
C2—C1—C6	121.2 (2)	C18—C17—C16	120.7 (3)
C2—C1—Cl1	119.44 (17)	C18—C17—H17	119.7
C6—C1—Cl1	119.39 (19)	C16—C17—H17	119.7
C1—C2—C3	120.8 (2)	C17—C18—C19	120.1 (3)
C1—C2—H2A	119.6	C17—C18—H18	120.0
C3—C2—H2A	119.6	C19—C18—H18	120.0
C2—C3—C4	119.1 (2)	C20—C19—C18	120.9 (3)
C2—C3—H3	120.5	C20—C19—H19	119.6
C4—C3—H3	120.5	C18—C19—H19	119.6
C5—C4—C3	119.6 (2)	O3—C20—C19	125.7 (2)
C5—C4—N2	117.2 (2)	O3—C20—C21	114.8 (2)
C3—C4—N2	123.2 (2)	C19—C20—C21	119.5 (2)
N1—C7—C8	122.2 (2)	O4—C21—C16	122.3 (2)
N1—C7—H7	118.9	O4—C21—C20	118.0 (2)
C8—C7—H7	118.9	C16—C21—C20	119.7 (2)
C9—C8—C13	119.0 (2)	O1—C14—H14A	109.5
C9—C8—C7	120.2 (2)	O1—C14—H14B	109.5
C13—C8—C7	120.8 (2)	H14A—C14—H14B	109.5
C10—C9—C8	120.7 (2)	O1—C14—H14C	109.5
C10—C9—H9	119.6	H14A—C14—H14C	109.5
C8—C9—H9	119.6	H14B—C14—H14C	109.5
C9—C10—C11	120.3 (2)	O3—C22—H22A	109.5
C9—C10—H10	119.8	O3—C22—H22B	109.5
C11—C10—H10	119.8	H22A—C22—H22B	109.5
C12—C11—C10	120.3 (2)	O3—C22—H22C	109.5
C12—C11—H11	119.8	H22A—C22—H22C	109.5
C10—C11—H11	119.8	H22B—C22—H22C	109.5

C4—C5—C6—C1	3.9 (3)	O1—C12—C13—O2	−0.1 (3)
C4—C5—C6—N1	−175.7 (2)	C11—C12—C13—O2	179.4 (2)
C7—N1—C6—C5	9.1 (3)	O1—C12—C13—C8	−179.99 (19)
C7—N1—C6—C1	−170.4 (2)	C11—C12—C13—C8	−0.5 (3)
C5—C6—C1—C2	−2.3 (3)	C9—C8—C13—O2	179.0 (2)
N1—C6—C1—C2	177.3 (2)	C7—C8—C13—O2	0.8 (3)
C5—C6—C1—Cl1	177.84 (16)	C9—C8—C13—C12	−1.1 (3)
N1—C6—C1—Cl1	−2.5 (3)	C7—C8—C13—C12	−179.4 (2)
C6—C1—C2—C3	−0.2 (4)	C4—N2—C15—C16	178.2 (2)
Cl1—C1—C2—C3	179.66 (18)	N2—C15—C16—C17	−173.3 (2)
C1—C2—C3—C4	1.2 (4)	N2—C15—C16—C21	2.5 (4)
C6—C5—C4—C3	−3.0 (3)	C21—C16—C17—C18	−0.5 (4)
C6—C5—C4—N2	179.5 (2)	C15—C16—C17—C18	175.4 (3)
C2—C3—C4—C5	0.3 (4)	C16—C17—C18—C19	1.1 (4)
C2—C3—C4—N2	177.6 (2)	C17—C18—C19—C20	−1.0 (4)
C15—N2—C4—C5	−140.9 (2)	C22—O3—C20—C19	1.8 (4)
C15—N2—C4—C3	41.7 (3)	C22—O3—C20—C21	−176.1 (2)
C6—N1—C7—C8	176.54 (19)	C18—C19—C20—O3	−177.6 (2)
N1—C7—C8—C9	−178.1 (2)	C18—C19—C20—C21	0.3 (4)
N1—C7—C8—C13	0.1 (3)	C17—C16—C21—O4	179.1 (2)
C13—C8—C9—C10	1.4 (3)	C15—C16—C21—O4	3.3 (3)
C7—C8—C9—C10	179.6 (2)	C17—C16—C21—C20	−0.2 (3)
C8—C9—C10—C11	0.0 (4)	C15—C16—C21—C20	−176.1 (2)
C9—C10—C11—C12	−1.6 (4)	O3—C20—C21—O4	−0.9 (3)
C14—O1—C12—C11	4.3 (4)	C19—C20—C21—O4	−179.0 (2)
C14—O1—C12—C13	−176.2 (2)	O3—C20—C21—C16	178.4 (2)
C10—C11—C12—O1	−178.7 (2)	C19—C20—C21—C16	0.3 (3)
C10—C11—C12—C13	1.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.83 (3)	1.81 (3)	2.586 (3)	155 (3)
O4—H4···N2	0.82 (3)	1.86 (3)	2.588 (3)	148 (3)
C11—H11···O4ⁱ	0.93	2.59	3.392 (3)	145
C3—H3···Cg3ⁱⁱ	0.93	2.89	3.635 (3)	138

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉ClN₂O₄
M_r	410.84
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.900 (2), 6.8589 (12), 28.830 (6)
β (°)	94.659 (4)
V (Å³)	1951.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.41 × 0.40 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.912, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	12204, 4049, 2758
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.131, 1.06
No. of reflections	4049
No. of parameters	272
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.83 (3)	1.81 (3)	2.586 (3)	155 (3)
O4—H4···N2	0.82 (3)	1.86 (3)	2.588 (3)	148 (3)
C11—H11···O4ⁱ	0.93	2.59	3.392 (3)	145
C3—H3···Cg3ⁱⁱ	0.93	2.89	3.635 (3)	138

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

Acknowledgements

The authors wish to thank both Universiti Teknologi MARA and Universiti Kebangsaan Malaysia for the facilities and the Malaysian Ministry of Higher Education for the research grant FRGS UiTM 5/3/FST/(12/2008).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Aranha, P. E., dos Santos, M. P., Romera, S. & Dockal, E. R. (2007). Polyhedron, 26, 1373–1382. Web of Science CrossRef CAS Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chetouani, A., Hammouti, B., Benhadda, T. & Daoudi, M. (2005). Appl. Surface Sci. 249, 375–385. Web of Science CrossRef CAS Google Scholar
Hernández-Molina, R., Mederos, A., Gili, P., Domínguez, S., Lloret, F., Cano, J., Julve, M., Ruiz-Pérez, C. & Solans, X. (1997). J. Chem. Soc. Dalton Trans. pp. 4327–4334. CSD CrossRef Web of Science Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Torayama, H., Nishide, T., Asada, H., Fujiwara, M. & Matsushita, T. (1997). Polyhedron, 16, 3787–3794. CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2573

doi:10.1107/S1600536809037386

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

6,6′-Dimeth­­oxy-2,2′-[(E,E′)-(4-chloro-m-phenyl­ene)bis­­(nitrilo­methyl­­idyne)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Dimethoxy-2,2′-[(E,E′)-(4-chloro-m-phenylene)bis(nitrilomethylidyne)]diphenol