6,6'-Dimeth-oxy-2,2'-[p-phenyl-ene-bis(nitrilo-methyl-idyne)]diphenol chloro-form disolvate.

The title compound, C(22)H(20)N(2)O(4)·2CHCl(3), a new Schiff base compound, lies across a crystallographic inversion centre. An intra-molecular O-H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. Inter-molecular bifurcated C-H⋯O hydrogen bonds involving the two O atoms of the Schiff base ligand and the H atom of the chloro-form solvent of crystallization, generate an R(2) (1)(5) ring motif. The crystal structure is stabilized by inter-molecular C-H⋯π and π-π inter-actions [centroid to centroid distance = 3.6158 (10) Å]. In the crystal structure, mol-ecules are stacked down the c axis.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the synthesis and applications of Schiff bases see, for example: Salem & Amer (1995 ▶); Teoh et al. (1997 ▶); Viswanathamurthi et al. (1998 ▶); Cohen et al. (1964 ▶); Kabak et al. (2000 ▶); Parra et al. (2007 ▶); Al-Douh et al. (2006 ▶, 2007 ▶, 2008 ▶); Liu et al. (2006 ▶); Shah et al. (2008 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H20N2O4·2CHCl3

M = 615.14

Monoclinic,

a = 10.4773 (2) Å

b = 21.3287 (5) Å

c = 6.2424 (2) Å

β = 105.669 (2)°

V = 1343.13 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.67 mm−1

T = 100 K

0.54 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.712, T max = 0.958

10624 measured reflections

3069 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.03

3069 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007302/at2731sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007302/at2731Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H20N2O4·2CHCl3	F(000) = 628
Mr = 615.14	Dx = 1.521 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3653 reflections
a = 10.4773 (2) Å	θ = 2.8–29.6°
b = 21.3287 (5) Å	µ = 0.67 mm−1
c = 6.2424 (2) Å	T = 100 K
β = 105.669 (2)°	Plate, yellow
V = 1343.13 (6) Å3	0.54 × 0.18 × 0.07 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3069 independent reflections
Radiation source: fine-focus sealed tube	2361 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.712, Tmax = 0.958	k = −27→27
10624 measured reflections	l = −8→8

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.6965P] where P = (Fo2 + 2Fc2)/3
3069 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.05508 (5)	0.10427 (3)	0.75969 (9)	0.03053 (15)
Cl2	0.09644 (5)	0.19372 (3)	0.43542 (10)	0.03061 (15)
Cl3	0.06333 (6)	0.06178 (3)	0.32245 (10)	0.03145 (15)
O1	0.71504 (12)	0.11003 (6)	0.4437 (2)	0.0159 (3)
H1	0.6880	0.0909	0.5406	0.024*
O2	0.76612 (13)	0.16921 (6)	0.1108 (2)	0.0167 (3)
N1	0.54474 (15)	0.06871 (7)	0.6416 (3)	0.0131 (3)
C1	0.61066 (18)	0.13631 (8)	0.2936 (3)	0.0126 (4)
C2	0.63590 (18)	0.16924 (8)	0.1137 (3)	0.0125 (4)
C3	0.53268 (19)	0.19797 (8)	−0.0409 (3)	0.0146 (4)
H3A	0.5499	0.2209	−0.1606	0.017*
C4	0.40308 (19)	0.19342 (8)	−0.0216 (3)	0.0159 (4)
H4A	0.3325	0.2128	−0.1295	0.019*
C5	0.37710 (18)	0.16110 (9)	0.1525 (3)	0.0153 (4)
H5A	0.2888	0.1583	0.1643	0.018*
C6	0.48096 (18)	0.13218 (8)	0.3132 (3)	0.0130 (4)
C7	0.45272 (19)	0.09798 (8)	0.4963 (3)	0.0147 (4)
H7A	0.3645	0.0971	0.5096	0.018*
C8	0.51663 (18)	0.03447 (8)	0.8182 (3)	0.0126 (4)
C9	0.62640 (18)	0.01408 (9)	0.9863 (3)	0.0153 (4)
H9A	0.7133	0.0235	0.9766	0.018*
C10	0.39007 (19)	0.01950 (9)	0.8339 (3)	0.0166 (4)
H10A	0.3146	0.0325	0.7202	0.020*
C11	0.7985 (2)	0.20505 (10)	−0.0612 (3)	0.0197 (4)
H11A	0.8939	0.2020	−0.0459	0.029*
H11B	0.7744	0.2490	−0.0487	0.029*
H11C	0.7493	0.1887	−0.2067	0.029*
C12	0.0159 (2)	0.12323 (10)	0.4736 (4)	0.0231 (5)
H12A	−0.0821	0.1294	0.4173	0.028*

	U11	U22	U33	U12	U13	U23
Cl1	0.0318 (3)	0.0392 (3)	0.0202 (3)	0.0063 (2)	0.0064 (2)	0.0025 (2)
Cl2	0.0281 (3)	0.0258 (3)	0.0401 (4)	−0.0015 (2)	0.0128 (2)	0.0010 (2)
Cl3	0.0394 (3)	0.0294 (3)	0.0264 (3)	−0.0015 (2)	0.0102 (2)	−0.0048 (2)
O1	0.0158 (6)	0.0169 (7)	0.0145 (7)	0.0007 (5)	0.0034 (5)	0.0060 (6)
O2	0.0184 (7)	0.0165 (7)	0.0168 (7)	0.0003 (5)	0.0079 (6)	0.0046 (6)
N1	0.0192 (8)	0.0095 (7)	0.0115 (8)	−0.0006 (6)	0.0053 (6)	0.0004 (6)
C1	0.0184 (9)	0.0062 (8)	0.0120 (9)	0.0000 (7)	0.0023 (7)	−0.0009 (7)
C2	0.0165 (9)	0.0087 (8)	0.0127 (9)	−0.0017 (7)	0.0047 (7)	−0.0021 (7)
C3	0.0230 (10)	0.0084 (9)	0.0124 (10)	−0.0012 (7)	0.0050 (8)	0.0004 (7)
C4	0.0195 (9)	0.0115 (9)	0.0143 (10)	0.0017 (7)	0.0005 (8)	0.0010 (8)
C5	0.0144 (9)	0.0128 (9)	0.0189 (10)	0.0006 (7)	0.0047 (8)	0.0000 (8)
C6	0.0188 (9)	0.0084 (8)	0.0121 (9)	−0.0021 (7)	0.0050 (7)	−0.0023 (7)
C7	0.0170 (9)	0.0116 (9)	0.0167 (10)	−0.0024 (7)	0.0066 (8)	−0.0008 (7)
C8	0.0188 (9)	0.0080 (8)	0.0126 (9)	0.0003 (7)	0.0070 (7)	−0.0024 (7)
C9	0.0151 (9)	0.0138 (9)	0.0186 (10)	−0.0007 (7)	0.0072 (8)	0.0011 (8)
C10	0.0171 (9)	0.0148 (9)	0.0164 (10)	0.0021 (7)	0.0021 (8)	0.0024 (8)
C11	0.0220 (10)	0.0222 (11)	0.0179 (11)	−0.0021 (8)	0.0105 (8)	0.0048 (8)
C12	0.0190 (10)	0.0284 (12)	0.0214 (11)	0.0022 (8)	0.0049 (8)	0.0025 (9)

Cl1—C12	1.768 (2)	C4—H4A	0.9500
Cl2—C12	1.771 (2)	C5—C6	1.408 (3)
Cl3—C12	1.763 (2)	C5—H5A	0.9500
O1—C1	1.354 (2)	C6—C7	1.452 (3)
O1—H1	0.8400	C7—H7A	0.9500
O2—C2	1.369 (2)	C8—C10	1.393 (3)
O2—C11	1.431 (2)	C8—C9	1.400 (3)
N1—C7	1.292 (2)	C9—C10i	1.381 (3)
N1—C8	1.418 (2)	C9—H9A	0.9500
C1—C6	1.400 (3)	C10—C9i	1.381 (3)
C1—C2	1.409 (3)	C10—H10A	0.9500
C2—C3	1.383 (3)	C11—H11A	0.9800
C3—C4	1.399 (3)	C11—H11B	0.9800
C3—H3A	0.9500	C11—H11C	0.9800
C4—C5	1.375 (3)	C12—H12A	1.0000
C1—O1—H1	109.5	C6—C7—H7A	119.2
C2—O2—C11	116.63 (14)	C10—C8—C9	118.75 (17)
C7—N1—C8	121.48 (16)	C10—C8—N1	125.04 (17)
O1—C1—C6	122.35 (17)	C9—C8—N1	116.21 (16)
O1—C1—C2	117.87 (16)	C10i—C9—C8	120.83 (18)
C6—C1—C2	119.78 (16)	C10i—C9—H9A	119.6
O2—C2—C3	125.84 (17)	C8—C9—H9A	119.6
O2—C2—C1	114.35 (15)	C9i—C10—C8	120.41 (17)
C3—C2—C1	119.81 (17)	C9i—C10—H10A	119.8
C2—C3—C4	120.26 (18)	C8—C10—H10A	119.8
C2—C3—H3A	119.9	O2—C11—H11A	109.5
C4—C3—H3A	119.9	O2—C11—H11B	109.5
C5—C4—C3	120.46 (17)	H11A—C11—H11B	109.5
C5—C4—H4A	119.8	O2—C11—H11C	109.5
C3—C4—H4A	119.8	H11A—C11—H11C	109.5
C4—C5—C6	120.21 (18)	H11B—C11—H11C	109.5
C4—C5—H5A	119.9	Cl3—C12—Cl1	110.39 (12)
C6—C5—H5A	119.9	Cl3—C12—Cl2	110.22 (12)
C1—C6—C5	119.47 (17)	Cl1—C12—Cl2	109.93 (12)
C1—C6—C7	120.62 (17)	Cl3—C12—H12A	108.7
C5—C6—C7	119.90 (17)	Cl1—C12—H12A	108.7
N1—C7—C6	121.54 (17)	Cl2—C12—H12A	108.7
N1—C7—H7A	119.2
C11—O2—C2—C3	3.6 (3)	C2—C1—C6—C7	179.44 (17)
C11—O2—C2—C1	−176.48 (16)	C4—C5—C6—C1	−0.3 (3)
O1—C1—C2—O2	1.5 (2)	C4—C5—C6—C7	−179.84 (17)
C6—C1—C2—O2	−179.08 (16)	C8—N1—C7—C6	−178.93 (16)
O1—C1—C2—C3	−178.60 (16)	C1—C6—C7—N1	−2.4 (3)
C6—C1—C2—C3	0.9 (3)	C5—C6—C7—N1	177.12 (17)
O2—C2—C3—C4	178.67 (17)	C7—N1—C8—C10	11.6 (3)
C1—C2—C3—C4	−1.3 (3)	C7—N1—C8—C9	−169.16 (17)
C2—C3—C4—C5	0.9 (3)	C10—C8—C9—C10i	−0.9 (3)
C3—C4—C5—C6	−0.1 (3)	N1—C8—C9—C10i	179.83 (17)
O1—C1—C6—C5	179.37 (17)	C9—C8—C10—C9i	0.9 (3)
C2—C1—C6—C5	−0.1 (3)	N1—C8—C10—C9i	−179.90 (17)
O1—C1—C6—C7	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.84	2.584 (2)	147
C12—H12A···O1ii	1.00	2.21	3.120 (3)	150
C12—H12A···O2ii	1.00	2.30	3.121 (3)	139
C3—H3A···Cg1iii	0.95	2.73	3.5221 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.84	2.584 (2)	147
C12—H12A⋯O1i	1.00	2.21	3.120 (3)	150
C12—H12A⋯O2i	1.00	2.30	3.121 (3)	139
C3—H3A⋯Cg1ii	0.95	2.73	3.5221 (19)	142

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1–C6 benzene ring.