6,6′-Dimeth­oxy-2,2′-[(E,E′)-(2,4,6-trimethyl-1,3-phenyl­ene)bis­(nitrilo­methanylyl­idene)]diphenol chloro­form monosolvate

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

doi:10.1107/S1600536812011531

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1176

doi:10.1107/S1600536812011531

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6,6′-Dimethoxy-2,2′-[(E,E′)-(2,4,6-trimethyl-1,3-phenylene)bis(nitrilomethanylylidene)]diphenol chloroform monosolvate

Hadariah Bahron,^a Najihah Abu Bakar,^a Bohari M. Yamin ^b and M. Sukeri M. Yusof ^c ^*

^aDepartment of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^bDepartment of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43650 Bangi, Selangor, Malaysia, and ^cDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia
^*Correspondence e-mail: mohdsukeri@umt.edu.my

(Received 8 March 2012; accepted 16 March 2012; online 24 March 2012)

In the title compound, C₂₅H₂₆N₂O₄·CHCl₃, the aromatic rings of the iminomethyl-6-methoxyphenol fragments make dihedral angles of 58.33 (6) and 87.74 (6)° with the central benzene ring. The molecular conformation is stabilized by intramolecular O—H⋯N hydrogen bonds. In the crystal, an intermolecular C—H⋯O hydrogen bond involving the chloroform solvent molecule is observed. The crystal packing is further stabilized by π–π stacking interactions [centroid–centroid distances = 3.739 (3)–3.776 (3) Å] between the benzene rings of centrosymmetrically related molecules.

Related literature

For a related structure, see: Yamin et al. (2009 ). For the synthetic procedure, see: Hernández-Molina et al. (1997 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₅H₂₆N₂O₄·CHCl₃
M_r = 537.85
Triclinic, $[P \overline 1]$
a = 10.162 (2) Å
b = 10.486 (2) Å
c = 12.640 (3) Å
α = 99.315 (4)°
β = 93.140 (4)°
γ = 90.196 (4)°
V = 1327.0 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 298 K
0.50 × 0.47 × 0.44 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.833, T_max = 0.851
14608 measured reflections
4947 independent reflections
3799 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.150
S = 1.04
4947 reflections
329 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89 (3)	1.76 (4)	2.566 (3)	150 (3)
O3—H3⋯N2	0.87 (4)	1.83 (4)	2.618 (2)	150 (4)
C26—H26⋯O1ⁱ	0.98	2.16	3.071 (4)	154
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S1600536812011531/rz2720sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011531/rz2720Isup2.hkl

checkCIF report

Comment top

The title compound is analogous to the previously reported compound 6,6'-Dimethoxy-2,2'-[(E,E')-(4-chloro-m-phenylene)bis(nitrilomethylidyne)]diphenol (Yamin et al., 2009) except for the presence of three methyl groups at positions 2, 4 and 6 and a solvate chloroform molecule (Fig. 1). The molecule exhibits a butterfly-like shape. The bond lengths are in the normal ranges (Allen et al., 1987) and comparable with those reported for similar molecules. One 2-iminomethyl-6-methoxyphenol wing (N1/C11—C17/O1/O2) is planar with a maximum deviation of 0.091 (4) Å for atom C17. The other wing (N2/C18—C25/O3/O4) is slightly twisted, with atom C25 deviating by 0.304 (4) Å. The central benzene ring (C1—C9) makes dihedral angle of 58.33 (6) and 87.74 (6) Å with N1/C11—C17/O1/O2 and O3/O4/C19—C24 wings, respectively. The dihedral angle between the two wings is 58.31 (10)°. There are two intramolecular O—H···N hydrogen bonds (Table 1) stabilizing the molecular conformation. In the crystal structure, weak intemolecular C—H···O hydrogen bonds are observed (Table 1) involving the chloroform solvated molecule (Fig. 2). The crystal packing is further stabilized by π–π stacking interactions occurring between centrosymmetrically-related molecules (Cg1···Cg1ⁱ = 3.776 (3) Å; Cg2···Cg2ⁱⁱ = 3.739 (3) Å; Cg1 and Cg2 are the centroids of the C19–C24 and C1–C6 rings, respectively (symmetry codes: (i) 1-x, -y, -z; (ii) 1-x, 1-y, 1-z).

Related literature top

For a related structure, see: Yamin et al. (2009). For the synthetic procedure, see: Hernández-Molina et al. (1997). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The Schiff base was synthesized by refluxing in ethanol 2,4,6-trimetyhl-1,3-phenylenediamine (0.4507 g, 3.0 mmol) and (o-vanillin (0.9998 g,6.0mmol) for 5 h as previously described by Hernández-Molina et al. (1997). The solvent was then evaporated off under reduced pressure. The viscous solution obtained was left in room conditions for a week affording a solid product which was recrystallized from chloroform. The yellow single crystals obtained were suitable for X-ray crystallographic investigation. Yield 92%. Melting point: 417–421 K. Analytical calculation for C₂₅H₂₆N₂O₄ [3CH₃-mpd(o -van)₂]: C, 71.75; H, 6.26; N, 6.69. Found: C, 71.90; H, 6.42; N, 6.84. 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 = 13.5027 (2H, s, OH), 8.364 (2H, s, HC=N), 7.061–6.898 (7H, m, H-Aryl), 3.975 (6H, s, OCH₃), 2.208 (6H, s, CH₃), 2.071 (3H, s, CH₃).

Structure description top

For a related structure, see: Yamin et al. (2009). For the synthetic procedure, see: Hernández-Molina et al. (1997). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. The molecular structure of the title compound, with displacement ellipsods drawn at the 50% probability level. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing diagram of the title compound approximately viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines.

6,6'-Dimethoxy-2,2'-[(E,E')-(2,4,6-trimethyl-1,3- phenylene)bis(nitrilomethanylylidene)]diphenol chloroform monosolvate top

Crystal data top

C₂₅H₂₆N₂O₄·CHCl₃	Z = 2
M_r = 537.85	F(000) = 560
Triclinic, P1	D_x = 1.346 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.162 (2) Å	Cell parameters from 5967 reflections
b = 10.486 (2) Å	θ = 2.0–25.5°
c = 12.640 (3) Å	µ = 0.38 mm⁻¹
α = 99.315 (4)°	T = 298 K
β = 93.140 (4)°	Block, colourless
γ = 90.196 (4)°	0.50 × 0.47 × 0.44 mm
V = 1327.0 (5) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4947 independent reflections
Radiation source: fine-focus sealed tube	3799 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.5°, θ_min = 2.0°
ω scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −12→12
T_min = 0.833, T_max = 0.851	l = −15→15
14608 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0709P)² + 0.542P] where P = (F_o² + 2F_c²)/3
4947 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₅H₂₆N₂O₄·CHCl₃	γ = 90.196 (4)°
M_r = 537.85	V = 1327.0 (5) Å³
Triclinic, P1	Z = 2
a = 10.162 (2) Å	Mo Kα radiation
b = 10.486 (2) Å	µ = 0.38 mm⁻¹
c = 12.640 (3) Å	T = 298 K
α = 99.315 (4)°	0.50 × 0.47 × 0.44 mm
β = 93.140 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4947 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3799 reflections with I > 2σ(I)
T_min = 0.833, T_max = 0.851	R_int = 0.017
14608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.42 e Å⁻³
4947 reflections	Δρ_min = −0.43 e Å⁻³
329 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	0.03110 (10)	0.62554 (11)	0.86722 (8)	0.1141 (4)
Cl2	0.27407 (11)	0.52065 (10)	0.93526 (9)	0.1134 (3)
Cl3	0.12916 (12)	0.69304 (10)	1.08602 (7)	0.1112 (4)
O1	0.66016 (19)	0.17533 (16)	0.16568 (15)	0.0666 (5)
O2	0.78095 (19)	0.01822 (19)	0.02179 (15)	0.0774 (5)
O3	0.24675 (16)	0.87363 (16)	0.38440 (18)	0.0742 (6)
O4	0.12149 (18)	1.08231 (16)	0.3545 (2)	0.0897 (7)
N1	0.47101 (18)	0.21937 (16)	0.29251 (15)	0.0518 (4)
N2	0.24295 (18)	0.62506 (16)	0.38954 (16)	0.0527 (4)
C1	0.4031 (2)	0.28405 (19)	0.47697 (18)	0.0500 (5)
C2	0.3505 (2)	0.3788 (2)	0.55115 (18)	0.0536 (5)
H2	0.3515	0.3665	0.6224	0.064*
C3	0.2966 (2)	0.4910 (2)	0.52441 (18)	0.0512 (5)
C4	0.2981 (2)	0.50847 (18)	0.41760 (18)	0.0473 (5)
C5	0.3573 (2)	0.42049 (19)	0.34071 (17)	0.0492 (5)
C6	0.4070 (2)	0.30635 (19)	0.37139 (18)	0.0474 (5)
C7	0.4551 (3)	0.1628 (2)	0.5135 (2)	0.0662 (6)
H7A	0.3897	0.0952	0.4967	0.099*
H7B	0.4750	0.1794	0.5896	0.099*
H7C	0.5336	0.1367	0.4774	0.099*
C8	0.2394 (3)	0.5905 (2)	0.6084 (2)	0.0705 (7)
H8A	0.1449	0.5873	0.5993	0.106*
H8B	0.2707	0.6749	0.6010	0.106*
H8C	0.2660	0.5726	0.6785	0.106*
C9	0.3669 (3)	0.4462 (2)	0.2278 (2)	0.0721 (7)
H9A	0.2897	0.4123	0.1851	0.108*
H9B	0.4437	0.4050	0.1977	0.108*
H9C	0.3735	0.5376	0.2283	0.108*
C10	0.4370 (2)	0.1001 (2)	0.26946 (18)	0.0520 (5)
H10	0.3665	0.0698	0.3027	0.062*
C11	0.5068 (2)	0.0109 (2)	0.19195 (18)	0.0515 (5)
C12	0.6140 (2)	0.0524 (2)	0.14253 (18)	0.0529 (5)
C13	0.6780 (2)	−0.0339 (2)	0.06563 (19)	0.0599 (6)
C14	0.6338 (3)	−0.1596 (2)	0.0417 (2)	0.0716 (7)
H14	0.6758	−0.2175	−0.0089	0.086*
C15	0.5280 (3)	−0.2015 (2)	0.0915 (2)	0.0767 (8)
H15	0.4998	−0.2872	0.0745	0.092*
C16	0.4642 (3)	−0.1179 (2)	0.1656 (2)	0.0655 (6)
H16	0.3927	−0.1467	0.1985	0.079*
C17	0.8454 (3)	−0.0624 (4)	−0.0602 (3)	0.1006 (11)
H17A	0.8850	−0.1334	−0.0315	0.151*
H17B	0.9125	−0.0134	−0.0870	0.151*
H17C	0.7824	−0.0949	−0.1177	0.151*
C18	0.1223 (2)	0.6255 (2)	0.36095 (18)	0.0513 (5)
H18	0.0749	0.5483	0.3533	0.062*
C19	0.0532 (2)	0.7410 (2)	0.33923 (17)	0.0498 (5)
C20	−0.0803 (2)	0.7342 (3)	0.3063 (2)	0.0689 (7)
H20	−0.1244	0.6549	0.2957	0.083*
C21	−0.1466 (3)	0.8424 (3)	0.2894 (3)	0.0801 (8)
H21	−0.2353	0.8364	0.2666	0.096*
C22	−0.0827 (3)	0.9608 (3)	0.3060 (2)	0.0720 (7)
H22	−0.1290	1.0346	0.2956	0.086*
C23	0.0486 (2)	0.9705 (2)	0.3378 (2)	0.0595 (6)
C24	0.1182 (2)	0.8603 (2)	0.35432 (18)	0.0499 (5)
C25	0.0571 (3)	1.1989 (3)	0.3692 (3)	0.0928 (10)
H25A	0.0083	1.2092	0.3040	0.139*
H25B	0.1205	1.2681	0.3880	0.139*
H25C	−0.0023	1.2005	0.4259	0.139*
C26	0.1719 (3)	0.6559 (3)	0.9533 (2)	0.0741 (7)
H26	0.2196	0.7299	0.9349	0.089*
H3	0.275 (3)	0.797 (4)	0.392 (3)	0.109 (11)*
H1	0.605 (3)	0.218 (3)	0.210 (3)	0.101 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1134 (7)	0.1233 (8)	0.0967 (6)	0.0259 (6)	−0.0080 (5)	−0.0049 (5)
Cl2	0.1231 (8)	0.1002 (7)	0.1177 (7)	0.0351 (6)	0.0131 (6)	0.0177 (5)
Cl3	0.1584 (9)	0.1091 (7)	0.0672 (5)	−0.0003 (6)	0.0309 (5)	0.0097 (4)
O1	0.0770 (12)	0.0468 (9)	0.0746 (11)	0.0004 (8)	0.0250 (9)	−0.0016 (8)
O2	0.0793 (12)	0.0798 (12)	0.0697 (11)	0.0162 (10)	0.0216 (9)	−0.0039 (9)
O3	0.0490 (9)	0.0427 (9)	0.1321 (17)	0.0056 (7)	−0.0044 (9)	0.0210 (10)
O4	0.0635 (11)	0.0417 (9)	0.167 (2)	0.0105 (8)	0.0093 (12)	0.0248 (11)
N1	0.0546 (10)	0.0388 (9)	0.0620 (11)	0.0110 (8)	0.0091 (8)	0.0065 (8)
N2	0.0534 (11)	0.0344 (9)	0.0710 (12)	0.0073 (7)	0.0058 (9)	0.0095 (8)
C1	0.0467 (11)	0.0418 (11)	0.0622 (13)	0.0061 (9)	0.0012 (10)	0.0108 (9)
C2	0.0590 (13)	0.0491 (12)	0.0537 (12)	0.0043 (10)	0.0039 (10)	0.0112 (10)
C3	0.0528 (12)	0.0405 (11)	0.0595 (13)	0.0037 (9)	0.0080 (10)	0.0035 (9)
C4	0.0465 (11)	0.0322 (10)	0.0632 (13)	0.0035 (8)	0.0039 (9)	0.0075 (9)
C5	0.0522 (12)	0.0391 (10)	0.0570 (12)	0.0042 (9)	0.0063 (9)	0.0086 (9)
C6	0.0442 (11)	0.0361 (10)	0.0611 (13)	0.0061 (8)	0.0058 (9)	0.0048 (9)
C7	0.0717 (16)	0.0554 (14)	0.0740 (16)	0.0197 (12)	−0.0027 (12)	0.0193 (12)
C8	0.0881 (18)	0.0522 (14)	0.0700 (16)	0.0146 (12)	0.0194 (14)	0.0012 (12)
C9	0.099 (2)	0.0565 (14)	0.0644 (15)	0.0228 (13)	0.0172 (14)	0.0164 (12)
C10	0.0503 (12)	0.0442 (12)	0.0611 (13)	0.0078 (9)	0.0026 (10)	0.0078 (10)
C11	0.0571 (13)	0.0389 (11)	0.0565 (12)	0.0099 (9)	−0.0030 (10)	0.0041 (9)
C12	0.0609 (13)	0.0429 (11)	0.0531 (12)	0.0129 (10)	−0.0018 (10)	0.0043 (9)
C13	0.0659 (15)	0.0569 (14)	0.0540 (13)	0.0201 (11)	−0.0001 (11)	0.0014 (10)
C14	0.0876 (19)	0.0573 (15)	0.0625 (15)	0.0236 (13)	−0.0011 (14)	−0.0115 (12)
C15	0.095 (2)	0.0425 (13)	0.0849 (19)	0.0075 (13)	−0.0076 (16)	−0.0082 (12)
C16	0.0721 (16)	0.0461 (13)	0.0753 (16)	0.0021 (11)	−0.0032 (13)	0.0034 (11)
C17	0.082 (2)	0.125 (3)	0.082 (2)	0.0240 (19)	0.0192 (16)	−0.0254 (19)
C18	0.0572 (13)	0.0373 (10)	0.0595 (13)	0.0008 (9)	0.0072 (10)	0.0066 (9)
C19	0.0520 (12)	0.0442 (11)	0.0544 (12)	0.0071 (9)	0.0059 (9)	0.0102 (9)
C20	0.0565 (14)	0.0592 (14)	0.0923 (19)	−0.0024 (11)	−0.0047 (13)	0.0196 (13)
C21	0.0532 (14)	0.0771 (18)	0.113 (2)	0.0059 (13)	−0.0115 (14)	0.0308 (16)
C22	0.0593 (15)	0.0619 (15)	0.101 (2)	0.0180 (12)	0.0056 (14)	0.0310 (14)
C23	0.0548 (13)	0.0452 (12)	0.0817 (16)	0.0100 (10)	0.0116 (11)	0.0177 (11)
C24	0.0452 (11)	0.0457 (11)	0.0603 (13)	0.0090 (9)	0.0083 (9)	0.0109 (9)
C25	0.086 (2)	0.0506 (15)	0.141 (3)	0.0160 (14)	0.0102 (19)	0.0142 (17)
C26	0.0911 (19)	0.0671 (16)	0.0665 (16)	−0.0008 (14)	0.0179 (14)	0.0136 (13)

Geometric parameters (Å, º) top

Cl1—C26	1.745 (3)	C9—H9B	0.9600
Cl2—C26	1.753 (3)	C9—H9C	0.9600
Cl3—C26	1.738 (3)	C10—C11	1.457 (3)
O1—C12	1.351 (3)	C10—H10	0.9300
O1—H1	0.89 (4)	C11—C12	1.388 (3)
O2—C13	1.363 (3)	C11—C16	1.399 (3)
O2—C17	1.419 (3)	C12—C13	1.406 (3)
O3—C24	1.340 (3)	C13—C14	1.372 (4)
O3—H3	0.88 (4)	C14—C15	1.380 (4)
O4—C23	1.366 (3)	C14—H14	0.9300
O4—C25	1.379 (3)	C15—C16	1.368 (4)
N1—C10	1.280 (3)	C15—H15	0.9300
N1—C6	1.425 (3)	C16—H16	0.9300
N2—C18	1.259 (3)	C17—H17A	0.9600
N2—C4	1.435 (3)	C17—H17B	0.9600
C1—C2	1.381 (3)	C17—H17C	0.9600
C1—C6	1.394 (3)	C18—C19	1.458 (3)
C1—C7	1.509 (3)	C18—H18	0.9300
C2—C3	1.383 (3)	C19—C24	1.394 (3)
C2—H2	0.9300	C19—C20	1.395 (3)
C3—C4	1.392 (3)	C20—C21	1.362 (4)
C3—C8	1.505 (3)	C20—H20	0.9300
C4—C5	1.391 (3)	C21—C22	1.380 (4)
C5—C6	1.404 (3)	C21—H21	0.9300
C5—C9	1.503 (3)	C22—C23	1.370 (3)
C7—H7A	0.9600	C22—H22	0.9300
C7—H7B	0.9600	C23—C24	1.396 (3)
C7—H7C	0.9600	C25—H25A	0.9600
C8—H8A	0.9600	C25—H25B	0.9600
C8—H8B	0.9600	C25—H25C	0.9600
C8—H8C	0.9600	C26—H26	0.9800
C9—H9A	0.9600

C12—O1—H1	106 (2)	O2—C13—C14	126.2 (2)
C13—O2—C17	117.6 (2)	O2—C13—C12	114.9 (2)
C24—O3—H3	107 (2)	C14—C13—C12	118.9 (2)
C23—O4—C25	118.9 (2)	C13—C14—C15	121.0 (2)
C10—N1—C6	121.59 (19)	C13—C14—H14	119.5
C18—N2—C4	118.54 (18)	C15—C14—H14	119.5
C2—C1—C6	117.92 (19)	C16—C15—C14	120.5 (2)
C2—C1—C7	119.0 (2)	C16—C15—H15	119.7
C6—C1—C7	123.0 (2)	C14—C15—H15	119.7
C1—C2—C3	123.1 (2)	C15—C16—C11	119.9 (3)
C1—C2—H2	118.5	C15—C16—H16	120.0
C3—C2—H2	118.5	C11—C16—H16	120.0
C2—C3—C4	117.53 (19)	O2—C17—H17A	109.5
C2—C3—C8	120.8 (2)	O2—C17—H17B	109.5
C4—C3—C8	121.6 (2)	H17A—C17—H17B	109.5
C5—C4—C3	121.95 (18)	O2—C17—H17C	109.5
C5—C4—N2	120.19 (19)	H17A—C17—H17C	109.5
C3—C4—N2	117.76 (18)	H17B—C17—H17C	109.5
C4—C5—C6	118.1 (2)	N2—C18—C19	123.36 (19)
C4—C5—C9	121.06 (19)	N2—C18—H18	118.3
C6—C5—C9	120.87 (19)	C19—C18—H18	118.3
C1—C6—C5	121.22 (19)	C24—C19—C20	119.0 (2)
C1—C6—N1	121.34 (18)	C24—C19—C18	120.59 (19)
C5—C6—N1	117.24 (19)	C20—C19—C18	120.4 (2)
C1—C7—H7A	109.5	C21—C20—C19	120.7 (2)
C1—C7—H7B	109.5	C21—C20—H20	119.7
H7A—C7—H7B	109.5	C19—C20—H20	119.7
C1—C7—H7C	109.5	C20—C21—C22	120.3 (2)
H7A—C7—H7C	109.5	C20—C21—H21	119.9
H7B—C7—H7C	109.5	C22—C21—H21	119.9
C3—C8—H8A	109.5	C23—C22—C21	120.4 (2)
C3—C8—H8B	109.5	C23—C22—H22	119.8
H8A—C8—H8B	109.5	C21—C22—H22	119.8
C3—C8—H8C	109.5	O4—C23—C22	125.1 (2)
H8A—C8—H8C	109.5	O4—C23—C24	114.9 (2)
H8B—C8—H8C	109.5	C22—C23—C24	120.0 (2)
C5—C9—H9A	109.5	O3—C24—C19	122.20 (18)
C5—C9—H9B	109.5	O3—C24—C23	118.2 (2)
H9A—C9—H9B	109.5	C19—C24—C23	119.6 (2)
C5—C9—H9C	109.5	O4—C25—H25A	109.5
H9A—C9—H9C	109.5	O4—C25—H25B	109.5
H9B—C9—H9C	109.5	H25A—C25—H25B	109.5
N1—C10—C11	121.1 (2)	O4—C25—H25C	109.5
N1—C10—H10	119.5	H25A—C25—H25C	109.5
C11—C10—H10	119.5	H25B—C25—H25C	109.5
C12—C11—C16	119.4 (2)	Cl3—C26—Cl1	110.58 (17)
C12—C11—C10	120.85 (19)	Cl3—C26—Cl2	110.98 (16)
C16—C11—C10	119.7 (2)	Cl1—C26—Cl2	109.26 (16)
O1—C12—C11	121.96 (19)	Cl3—C26—H26	108.7
O1—C12—C13	117.9 (2)	Cl1—C26—H26	108.7
C11—C12—C13	120.2 (2)	Cl2—C26—H26	108.7

C6—C1—C2—C3	3.1 (3)	C17—O2—C13—C14	3.3 (4)
C7—C1—C2—C3	−177.8 (2)	C17—O2—C13—C12	−176.9 (2)
C1—C2—C3—C4	−1.0 (3)	O1—C12—C13—O2	−0.5 (3)
C1—C2—C3—C8	179.3 (2)	C11—C12—C13—O2	179.3 (2)
C2—C3—C4—C5	−3.3 (3)	O1—C12—C13—C14	179.3 (2)
C8—C3—C4—C5	176.4 (2)	C11—C12—C13—C14	−0.9 (3)
C2—C3—C4—N2	−179.66 (19)	O2—C13—C14—C15	−180.0 (2)
C8—C3—C4—N2	0.0 (3)	C12—C13—C14—C15	0.3 (4)
C18—N2—C4—C5	93.5 (3)	C13—C14—C15—C16	0.4 (4)
C18—N2—C4—C3	−90.1 (3)	C14—C15—C16—C11	−0.4 (4)
C3—C4—C5—C6	5.2 (3)	C12—C11—C16—C15	−0.2 (3)
N2—C4—C5—C6	−178.49 (19)	C10—C11—C16—C15	178.8 (2)
C3—C4—C5—C9	−175.3 (2)	C4—N2—C18—C19	174.8 (2)
N2—C4—C5—C9	1.0 (3)	N2—C18—C19—C24	−3.0 (3)
C2—C1—C6—C5	−1.0 (3)	N2—C18—C19—C20	179.1 (2)
C7—C1—C6—C5	179.9 (2)	C24—C19—C20—C21	−0.2 (4)
C2—C1—C6—N1	173.84 (19)	C18—C19—C20—C21	177.7 (3)
C7—C1—C6—N1	−5.2 (3)	C19—C20—C21—C22	−0.8 (5)
C4—C5—C6—C1	−3.0 (3)	C20—C21—C22—C23	1.2 (5)
C9—C5—C6—C1	177.5 (2)	C25—O4—C23—C22	18.3 (4)
C4—C5—C6—N1	−178.06 (18)	C25—O4—C23—C24	−162.4 (3)
C9—C5—C6—N1	2.4 (3)	C21—C22—C23—O4	178.7 (3)
C10—N1—C6—C1	58.0 (3)	C21—C22—C23—C24	−0.5 (4)
C10—N1—C6—C5	−126.9 (2)	C20—C19—C24—O3	−179.0 (2)
C6—N1—C10—C11	−177.39 (19)	C18—C19—C24—O3	3.0 (3)
N1—C10—C11—C12	1.3 (3)	C20—C19—C24—C23	0.9 (3)
N1—C10—C11—C16	−177.7 (2)	C18—C19—C24—C23	−177.1 (2)
C16—C11—C12—O1	−179.3 (2)	O4—C23—C24—O3	0.1 (3)
C10—C11—C12—O1	1.7 (3)	C22—C23—C24—O3	179.4 (2)
C16—C11—C12—C13	0.8 (3)	O4—C23—C24—C19	−179.9 (2)
C10—C11—C12—C13	−178.2 (2)	C22—C23—C24—C19	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89 (3)	1.76 (4)	2.566 (3)	150 (3)
O3—H3···N2	0.87 (4)	1.83 (4)	2.618 (2)	150 (4)
C26—H26···O1ⁱ	0.98	2.16	3.071 (4)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂O₄·CHCl₃
M_r	537.85
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.162 (2), 10.486 (2), 12.640 (3)
α, β, γ (°)	99.315 (4), 93.140 (4), 90.196 (4)
V (Å³)	1327.0 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.50 × 0.47 × 0.44

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.833, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	14608, 4947, 3799
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.150, 1.04
No. of reflections	4947
No. of parameters	329
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.43

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
O1—H1···N1	0.89 (3)	1.76 (4)	2.566 (3)	150 (3)
O3—H3···N2	0.87 (4)	1.83 (4)	2.618 (2)	150 (4)
C26—H26···O1ⁱ	0.98	2.16	3.071 (4)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors wish to thank Universiti Teknologi MARA, Universiti Malaysia Terengganu and Universiti Kebangsaan Malaysia for the research facilities and the Ministry of Higher Education Malaysia 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. CSD CrossRef Web of Science Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Yamin, B. M., Bakar, S. N. A., Kassim, K. & Bahron, H. (2009). Acta Cryst. E65, o2573. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o1176

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

6,6′-Dimeth­­oxy-2,2′-[(E,E′)-(2,4,6-tri­methyl-1,3-phenyl­ene)bis­­(nitrilo­methanylyl­­idene)]diphenol chloro­form monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Dimethoxy-2,2′-[(E,E′)-(2,4,6-trimethyl-1,3-phenylene)bis(nitrilomethanylylidene)]diphenol chloroform monosolvate