(±)-trans-6,6′-Dieth­oxy-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenol monohydrate

Mohan, N.; Sreejith, S.S.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536814000713

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o182-o183

doi:10.1107/S1600536814000713

Open

access

(±)-trans-6,6′-Diethoxy-2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol monohydrate

Nithya Mohan,^a S. S. Sreejith,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^a

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
^*Correspondence e-mail: eesans@yahoo.com

(Received 21 November 2013; accepted 11 January 2014; online 22 January 2014)

In the title hydrate, C₂₄H₃₀N₂O₄·H₂O, the organic molecule adopts an E conformation with respect to the azomethine double bonds. The cyclohexane ring is in a chair conformation. The dihedral angle between benzene rings is 79.6 (2)°. Two intramolecular O—H⋯N hydrogen bonds are present. In the crystal, the components are linked by O–H⋯O hydrogen bonds and weak C—H⋯π interactions, generating a three-dimensional supramolecular architecture.

CCDC reference: 981065

Related literature

For applications of Schiff bases, see: Franceschi et al. (1999 ); Hwang et al. (1998 ); Popović et al. (2002 ); Jones et al. (1979 ). For a related structure, see: Ambili et al. (2012 ). For the synthesis of Schiff bases, see: Tümer (2000 ). For ring puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₃₀N₂O₄·H₂O
M_r = 428.52
Monoclinic, P 2₁ /c
a = 9.8241 (18) Å
b = 11.6975 (19) Å
c = 21.881 (4) Å
β = 111.144 (8)°
V = 2345.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.977, T_max = 0.980
16141 measured reflections
5586 independent reflections
2701 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.190
S = 1.01
5586 reflections
299 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3′⋯N2	0.85 (1)	1.77 (3)	2.550 (4)	152 (3)
O2—H2′⋯N1	0.84 (1)	1.85 (2)	2.584 (3)	144 (4)
O1W—H1B⋯O3	0.86 (5)	2.34 (7)	3.005 (5)	134 (8)
O1W—H1B⋯O4	0.86 (5)	2.38 (8)	3.052 (5)	135 (6)
C21—H21B⋯Cg	0.97	2.92	3.810 (4)	153

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 981065

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814000713/fj2654sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000713/fj2654Isup2.hkl

checkCIF report

Comment top

Schiff bases are an important class of ligands in molecular design devoted to energy storage such as molecular batteries (Franceschi, et al. 1999) and also in transition metal catalysis (Hwang, et al. 1998). Schiff base having intramolecular hydrogen bonding shows photophysical properties such as thermochromism and photochromism (Popović, et al. 2002). Schiff bases also have an ability to reversibly bind oxygen (Jones, et al.1979).

The title compound crystallizes in the monoclinic, P2₁/c space group. The bond lengths and the bond angles agree with the related structure (Ambili, et al., 2012). The torsional angle, 177.9 (3)° of the azomethine linkage, C9—N2—C14—C15 reveals that the title compound adopts E conformation (Fig. 1). The mean plane deviation calculations show that the molecule as a whole is non-planar. Ring puckering analysis (Cremer & Pople, 1975) and least square plane calculations show that the cyclohexyl ring adopts a chair conformation (Q_T = 0.565 (4) Å) with the equatorial substitution at C9 for N2 and axial substitution at C8 for N1.

Crystal system consists of intramolecular hydrogen bonds of lengths 1.79 (3) Å and 1.85 (3) Å which exists between the azomethine N atom and the neighbouring phenolic O atom leading to the formation of two six membered rings comprising of atoms C14—C15—C20—O3—H3'···N2 and C7—C6—C5—O2—H2'···N1 (Fig. 2). A C—H···π interaction between one of the hydrogen attached at C21 and the aromatic ring (C15—C20) with H···Cg distance of 2.92 Å (Fig. 3) dominates the packing of molecules in the lattice. Fig. 4 shows the packing diagram of the title compound along a axis.

Related literature top

For applications of Schiff bases, see: Franceschi et al. (1999); Hwang et al. (1998); Popović et al. (2002); Jones et al. (1979). For a related structure, see: Ambili et al. (2012). For the synthesis of Schiff bases, see: Tümer (2000). For ring puckering analysis, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared by following the reported procedure (Tümer, 2000). 3-Ethoxy-2-hydroxybenzaldehyde (0.166 g,1 mmol) was dissolved in ethanol and an ethanolic solution of 1, 2-diaminocyclohexane (0.044 g, 0.5 mmol) was added to it. The mixture was refluxed for 5 h. Slow evaporation of the solution yielded 0.183 g (95%) yellow block type crystals of (±)-trans-6,6'-Diethoxy-2,2'-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol monohydrate. The compound melts at 115 °C.

IR (KBr, \v in cm^-1): 1626, 3530, 2930, 1468, 1249 ¹H NMR (400 MHz, CDCl₃, δ in p.p.m.): 13.871 (s, 2H), 8.231 (s, 2H), 4.093–4.041 (q, 4H), 1.442–1.477 (t, 6H), 6.679–6.686 (m, 6H), 1.589–1.953 (m, 10H)

Structure description top

For applications of Schiff bases, see: Franceschi et al. (1999); Hwang et al. (1998); Popović et al. (2002); Jones et al. (1979). For a related structure, see: Ambili et al. (2012). For the synthesis of Schiff bases, see: Tümer (2000). For ring puckering analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP diagram of the unique part of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Intramolecular hydrogen bonds present in the compound.
	Fig. 3. C—H···π interactions found in the title compound.
	Fig. 4. Packing diagram of the compound viewed along a axis.

(±)-trans-6,6'-Diethoxy-2,2'-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol monohydrate top

Crystal data top

C₂₄H₃₀N₂O₄·H₂O	F(000) = 920
M_r = 428.52	D_x = 1.214 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3026 reflections
a = 9.8241 (18) Å	θ = 2.8–23.5°
b = 11.6975 (19) Å	µ = 0.09 mm⁻¹
c = 21.881 (4) Å	T = 293 K
β = 111.144 (8)°	Block, yellow
V = 2345.2 (7) Å³	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5586 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 8.33 pixels mm^-1	θ_max = 28.0°, θ_min = 2.4°
ω and φ scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −15→15
T_min = 0.977, T_max = 0.980	l = −28→28
16141 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.190	w = 1/[σ²(F_o²) + (0.0561P)² + 1.8063P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5586 reflections	Δρ_max = 0.24 e Å⁻³
299 parameters	Δρ_min = −0.21 e Å⁻³
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (8)

Crystal data top

C₂₄H₃₀N₂O₄·H₂O	V = 2345.2 (7) Å³
M_r = 428.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8241 (18) Å	µ = 0.09 mm⁻¹
b = 11.6975 (19) Å	T = 293 K
c = 21.881 (4) Å	0.40 × 0.20 × 0.20 mm
β = 111.144 (8)°

Data collection top

Bruker APEXII CCD diffractometer	5586 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2701 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.980	R_int = 0.048
16141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	5 restraints
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.24 e Å⁻³
5586 reflections	Δρ_min = −0.21 e Å⁻³
299 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	0.7073 (2)	0.08906 (17)	0.34718 (12)	0.0591 (6)
O2	0.8516 (2)	0.28131 (19)	0.35839 (14)	0.0629 (7)
O3	0.7204 (3)	0.4164 (2)	0.18225 (11)	0.0538 (6)
O4	0.5589 (2)	0.32967 (18)	0.06864 (10)	0.0547 (6)
N1	0.8533 (3)	0.5022 (2)	0.35838 (12)	0.0449 (6)
N2	0.9286 (3)	0.5466 (2)	0.24970 (12)	0.0466 (6)
C1	0.4960 (3)	0.3961 (3)	0.34503 (16)	0.0508 (8)
H1	0.4499	0.4658	0.3442	0.061*
C2	0.4199 (4)	0.2961 (3)	0.34086 (17)	0.0574 (9)
H2	0.3232	0.2984	0.3380	0.069*
C3	0.4869 (3)	0.1916 (3)	0.34092 (15)	0.0496 (8)
H3	0.4339	0.1243	0.3369	0.060*
C4	0.6311 (3)	0.1869 (2)	0.34687 (14)	0.0420 (7)
C5	0.7104 (3)	0.2888 (2)	0.35266 (14)	0.0400 (7)
C6	0.6415 (3)	0.3937 (2)	0.35044 (13)	0.0382 (7)
C7	0.7186 (3)	0.5000 (2)	0.35060 (14)	0.0424 (7)
H7A	0.6677	0.5686	0.3448	0.051*
C8	0.9215 (3)	0.6119 (2)	0.35447 (16)	0.0471 (8)
H8	0.8450	0.6678	0.3328	0.056*
C9	1.0171 (3)	0.5952 (3)	0.31316 (15)	0.0462 (8)
H9	1.0533	0.6701	0.3058	0.055*
C10	1.1468 (3)	0.5191 (3)	0.34789 (16)	0.0539 (8)
H10A	1.2077	0.5135	0.3217	0.065*
H10B	1.1125	0.4430	0.3524	0.065*
C11	1.2369 (4)	0.5653 (3)	0.41526 (18)	0.0676 (10)
H11A	1.2790	0.6384	0.4106	0.081*
H11B	1.3162	0.5129	0.4369	0.081*
C12	1.1432 (4)	0.5804 (3)	0.45706 (18)	0.0711 (11)
H12A	1.1098	0.5063	0.4657	0.085*
H12B	1.2013	0.6145	0.4987	0.085*
C13	1.0126 (4)	0.6560 (3)	0.42242 (18)	0.0642 (10)
H13A	1.0466	0.7326	0.4185	0.077*
H13B	0.9517	0.6606	0.4487	0.077*
C14	0.9536 (3)	0.5704 (3)	0.19771 (16)	0.0497 (8)
H14	1.0277	0.6217	0.2002	0.060*
C15	0.8699 (3)	0.5199 (3)	0.13530 (14)	0.0426 (7)
C16	0.9044 (4)	0.5437 (3)	0.07977 (17)	0.0597 (9)
H16	0.9810	0.5929	0.0830	0.072*
C17	0.8259 (4)	0.4948 (3)	0.02104 (17)	0.0640 (10)
H17	0.8501	0.5100	−0.0155	0.077*
C18	0.7098 (4)	0.4224 (3)	0.01536 (15)	0.0535 (8)
H18	0.6567	0.3899	−0.0250	0.064*
C19	0.6726 (3)	0.3985 (2)	0.06895 (15)	0.0419 (7)
C20	0.7557 (3)	0.4444 (2)	0.13042 (14)	0.0403 (7)
C21	0.4662 (4)	0.2842 (3)	0.00700 (16)	0.0575 (9)
H21A	0.5221	0.2365	−0.0117	0.069*
H21B	0.4222	0.3458	−0.0235	0.069*
C22	0.3504 (4)	0.2149 (3)	0.0195 (2)	0.0823 (12)
H22A	0.2975	0.2627	0.0389	0.124*
H22B	0.3951	0.1532	0.0487	0.124*
H22C	0.2844	0.1846	−0.0212	0.124*
C23	0.7313 (5)	−0.1081 (3)	0.3322 (2)	0.0803 (12)
H23A	0.8103	−0.1114	0.3737	0.120*
H23B	0.7691	−0.0918	0.2983	0.120*
H23C	0.6814	−0.1803	0.3234	0.120*
C24	0.6272 (4)	−0.0162 (3)	0.33377 (19)	0.0616 (9)
H24A	0.5469	−0.0118	0.2920	0.074*
H24B	0.5878	−0.0319	0.3677	0.074*
O1W	0.5867 (5)	0.1883 (3)	0.1898 (2)	0.1125 (13)
H3'	0.786 (3)	0.447 (3)	0.2150 (13)	0.108 (17)*
H2'	0.890 (4)	0.3467 (17)	0.362 (2)	0.091 (14)*
H1A	0.635 (10)	0.203 (8)	0.2306 (13)	0.32 (6)*
H1B	0.573 (11)	0.255 (3)	0.172 (4)	0.31 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0575 (15)	0.0360 (12)	0.0902 (17)	0.0028 (11)	0.0343 (13)	−0.0022 (11)
O2	0.0410 (13)	0.0402 (14)	0.118 (2)	0.0047 (11)	0.0407 (14)	−0.0023 (14)
O3	0.0549 (14)	0.0642 (15)	0.0469 (13)	−0.0202 (12)	0.0240 (12)	−0.0055 (12)
O4	0.0559 (14)	0.0564 (14)	0.0502 (13)	−0.0196 (11)	0.0172 (11)	−0.0078 (11)
N1	0.0388 (15)	0.0399 (14)	0.0600 (16)	0.0007 (12)	0.0225 (13)	−0.0034 (12)
N2	0.0411 (15)	0.0477 (15)	0.0517 (16)	−0.0072 (12)	0.0175 (13)	−0.0053 (12)
C1	0.0396 (18)	0.0480 (18)	0.071 (2)	0.0099 (15)	0.0274 (17)	0.0086 (16)
C2	0.0392 (18)	0.062 (2)	0.078 (2)	0.0021 (17)	0.0295 (17)	0.0112 (18)
C3	0.0453 (19)	0.0455 (18)	0.062 (2)	−0.0063 (15)	0.0246 (16)	0.0087 (15)
C4	0.0448 (18)	0.0382 (16)	0.0466 (17)	0.0036 (14)	0.0207 (14)	0.0044 (13)
C5	0.0339 (16)	0.0414 (16)	0.0485 (17)	0.0059 (13)	0.0193 (14)	0.0030 (14)
C6	0.0351 (16)	0.0401 (16)	0.0422 (16)	0.0070 (13)	0.0173 (13)	0.0034 (13)
C7	0.0432 (18)	0.0379 (16)	0.0493 (18)	0.0074 (14)	0.0204 (15)	−0.0012 (14)
C8	0.0428 (18)	0.0366 (16)	0.063 (2)	−0.0031 (14)	0.0207 (16)	−0.0086 (15)
C9	0.0417 (18)	0.0417 (17)	0.0575 (19)	−0.0112 (14)	0.0206 (15)	−0.0078 (15)
C10	0.0363 (18)	0.060 (2)	0.068 (2)	−0.0026 (16)	0.0219 (16)	−0.0094 (17)
C11	0.045 (2)	0.079 (3)	0.071 (2)	−0.0057 (19)	0.0107 (18)	0.000 (2)
C12	0.069 (3)	0.080 (3)	0.060 (2)	−0.015 (2)	0.017 (2)	−0.009 (2)
C13	0.071 (2)	0.056 (2)	0.074 (2)	−0.0132 (19)	0.036 (2)	−0.0205 (19)
C14	0.0391 (18)	0.0450 (18)	0.068 (2)	−0.0075 (14)	0.0234 (16)	0.0032 (16)
C15	0.0343 (16)	0.0479 (17)	0.0481 (18)	−0.0030 (14)	0.0178 (14)	−0.0008 (14)
C16	0.051 (2)	0.073 (2)	0.062 (2)	−0.0134 (18)	0.0286 (18)	0.0062 (18)
C17	0.061 (2)	0.086 (3)	0.054 (2)	−0.009 (2)	0.0308 (19)	0.005 (2)
C18	0.053 (2)	0.064 (2)	0.0451 (18)	0.0004 (17)	0.0188 (16)	−0.0038 (16)
C19	0.0383 (17)	0.0400 (16)	0.0498 (18)	0.0002 (14)	0.0187 (14)	−0.0014 (14)
C20	0.0406 (17)	0.0381 (16)	0.0467 (17)	0.0015 (13)	0.0209 (14)	0.0029 (13)
C21	0.059 (2)	0.053 (2)	0.056 (2)	−0.0073 (17)	0.0149 (17)	−0.0087 (17)
C22	0.080 (3)	0.074 (3)	0.086 (3)	−0.036 (2)	0.020 (2)	−0.016 (2)
C23	0.098 (3)	0.047 (2)	0.101 (3)	0.008 (2)	0.042 (3)	−0.010 (2)
C24	0.068 (2)	0.0397 (18)	0.078 (2)	−0.0062 (17)	0.028 (2)	−0.0051 (17)
O1W	0.177 (4)	0.085 (2)	0.090 (2)	−0.048 (2)	0.066 (3)	−0.0119 (18)

Geometric parameters (Å, º) top

O1—C4	1.366 (3)	C11—H11A	0.9700
O1—C24	1.433 (4)	C11—H11B	0.9700
O2—C5	1.350 (3)	C12—C13	1.517 (5)
O2—H2'	0.846 (10)	C12—H12A	0.9700
O3—C20	1.341 (3)	C12—H12B	0.9700
O3—H3'	0.850 (10)	C13—H13A	0.9700
O4—C19	1.375 (3)	C13—H13B	0.9700
O4—C21	1.430 (4)	C14—C15	1.442 (4)
N1—C7	1.272 (3)	C14—H14	0.9300
N1—C8	1.465 (4)	C15—C20	1.401 (4)
N2—C14	1.278 (4)	C15—C16	1.402 (4)
N2—C9	1.461 (4)	C16—C17	1.363 (5)
C1—C2	1.373 (4)	C16—H16	0.9300
C1—C6	1.392 (4)	C17—C18	1.389 (5)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.388 (4)	C18—C19	1.377 (4)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.377 (4)	C19—C20	1.404 (4)
C3—H3	0.9300	C21—C22	1.501 (5)
C4—C5	1.405 (4)	C21—H21A	0.9700
C5—C6	1.394 (4)	C21—H21B	0.9700
C6—C7	1.455 (4)	C22—H22A	0.9600
C7—H7A	0.9300	C22—H22B	0.9600
C8—C13	1.522 (5)	C22—H22C	0.9600
C8—C9	1.533 (4)	C23—C24	1.493 (5)
C8—H8	0.9800	C23—H23A	0.9600
C9—C10	1.514 (4)	C23—H23B	0.9600
C9—H9	0.9800	C23—H23C	0.9600
C10—C11	1.519 (4)	C24—H24A	0.9700
C10—H10A	0.9700	C24—H24B	0.9700
C10—H10B	0.9700	O1W—H1A	0.864 (10)
C11—C12	1.524 (5)	O1W—H1B	0.866 (10)

C4—O1—C24	117.3 (2)	C11—C12—H12B	109.5
C5—O2—H2'	111 (3)	H12A—C12—H12B	108.1
C20—O3—H3'	105 (3)	C12—C13—C8	112.6 (3)
C19—O4—C21	117.5 (2)	C12—C13—H13A	109.1
C7—N1—C8	119.0 (2)	C8—C13—H13A	109.1
C14—N2—C9	121.5 (3)	C12—C13—H13B	109.1
C2—C1—C6	120.5 (3)	C8—C13—H13B	109.1
C2—C1—H1	119.8	H13A—C13—H13B	107.8
C6—C1—H1	119.8	N2—C14—C15	121.8 (3)
C1—C2—C3	120.2 (3)	N2—C14—H14	119.1
C1—C2—H2	119.9	C15—C14—H14	119.1
C3—C2—H2	119.9	C20—C15—C16	119.7 (3)
C4—C3—C2	120.4 (3)	C20—C15—C14	119.8 (3)
C4—C3—H3	119.8	C16—C15—C14	120.4 (3)
C2—C3—H3	119.8	C17—C16—C15	120.2 (3)
O1—C4—C3	125.2 (3)	C17—C16—H16	119.9
O1—C4—C5	115.2 (2)	C15—C16—H16	119.9
C3—C4—C5	119.6 (3)	C16—C17—C18	120.5 (3)
O2—C5—C6	122.0 (3)	C16—C17—H17	119.8
O2—C5—C4	118.1 (2)	C18—C17—H17	119.8
C6—C5—C4	119.8 (2)	C19—C18—C17	120.6 (3)
C1—C6—C5	119.4 (3)	C19—C18—H18	119.7
C1—C6—C7	120.1 (3)	C17—C18—H18	119.7
C5—C6—C7	120.4 (2)	O4—C19—C18	125.4 (3)
N1—C7—C6	122.2 (3)	O4—C19—C20	114.8 (2)
N1—C7—H7A	118.9	C18—C19—C20	119.8 (3)
C6—C7—H7A	118.9	O3—C20—C15	122.3 (3)
N1—C8—C13	111.1 (3)	O3—C20—C19	118.6 (3)
N1—C8—C9	108.2 (2)	C15—C20—C19	119.1 (3)
C13—C8—C9	110.5 (3)	O4—C21—C22	107.2 (3)
N1—C8—H8	109.0	O4—C21—H21A	110.3
C13—C8—H8	109.0	C22—C21—H21A	110.3
C9—C8—H8	109.0	O4—C21—H21B	110.3
N2—C9—C10	110.7 (2)	C22—C21—H21B	110.3
N2—C9—C8	109.2 (2)	H21A—C21—H21B	108.5
C10—C9—C8	111.3 (3)	C21—C22—H22A	109.5
N2—C9—H9	108.6	C21—C22—H22B	109.5
C10—C9—H9	108.6	H22A—C22—H22B	109.5
C8—C9—H9	108.6	C21—C22—H22C	109.5
C9—C10—C11	111.6 (3)	H22A—C22—H22C	109.5
C9—C10—H10A	109.3	H22B—C22—H22C	109.5
C11—C10—H10A	109.3	C24—C23—H23A	109.5
C9—C10—H10B	109.3	C24—C23—H23B	109.5
C11—C10—H10B	109.3	H23A—C23—H23B	109.5
H10A—C10—H10B	108.0	C24—C23—H23C	109.5
C10—C11—C12	110.9 (3)	H23A—C23—H23C	109.5
C10—C11—H11A	109.5	H23B—C23—H23C	109.5
C12—C11—H11A	109.5	O1—C24—C23	107.1 (3)
C10—C11—H11B	109.5	O1—C24—H24A	110.3
C12—C11—H11B	109.5	C23—C24—H24A	110.3
H11A—C11—H11B	108.0	O1—C24—H24B	110.3
C13—C12—C11	110.6 (3)	C23—C24—H24B	110.3
C13—C12—H12A	109.5	H24A—C24—H24B	108.6
C11—C12—H12A	109.5	H1A—O1W—H1B	103 (2)
C13—C12—H12B	109.5

C6—C1—C2—C3	−1.1 (5)	C8—C9—C10—C11	−56.0 (3)
C1—C2—C3—C4	1.7 (5)	C9—C10—C11—C12	56.5 (4)
C24—O1—C4—C3	6.5 (4)	C10—C11—C12—C13	−55.5 (4)
C24—O1—C4—C5	−172.9 (3)	C11—C12—C13—C8	55.4 (4)
C2—C3—C4—O1	−179.7 (3)	N1—C8—C13—C12	65.6 (3)
C2—C3—C4—C5	−0.2 (5)	C9—C8—C13—C12	−54.6 (4)
O1—C4—C5—O2	−0.5 (4)	C9—N2—C14—C15	177.9 (3)
C3—C4—C5—O2	−180.0 (3)	N2—C14—C15—C20	1.4 (5)
O1—C4—C5—C6	177.6 (3)	N2—C14—C15—C16	−177.0 (3)
C3—C4—C5—C6	−1.9 (4)	C20—C15—C16—C17	0.9 (5)
C2—C1—C6—C5	−1.0 (5)	C14—C15—C16—C17	179.3 (3)
C2—C1—C6—C7	176.1 (3)	C15—C16—C17—C18	0.9 (6)
O2—C5—C6—C1	−179.5 (3)	C16—C17—C18—C19	−0.3 (5)
C4—C5—C6—C1	2.5 (4)	C21—O4—C19—C18	−3.8 (4)
O2—C5—C6—C7	3.5 (4)	C21—O4—C19—C20	177.3 (3)
C4—C5—C6—C7	−174.6 (3)	C17—C18—C19—O4	179.0 (3)
C8—N1—C7—C6	176.8 (3)	C17—C18—C19—C20	−2.2 (5)
C1—C6—C7—N1	176.8 (3)	C16—C15—C20—O3	178.3 (3)
C5—C6—C7—N1	−6.2 (4)	C14—C15—C20—O3	−0.1 (4)
C7—N1—C8—C13	102.7 (3)	C16—C15—C20—C19	−3.3 (4)
C7—N1—C8—C9	−135.8 (3)	C14—C15—C20—C19	178.2 (3)
C14—N2—C9—C10	−89.5 (3)	O4—C19—C20—O3	1.4 (4)
C14—N2—C9—C8	147.7 (3)	C18—C19—C20—O3	−177.6 (3)
N1—C8—C9—N2	54.9 (3)	O4—C19—C20—C15	−177.1 (2)
C13—C8—C9—N2	176.7 (3)	C18—C19—C20—C15	4.0 (4)
N1—C8—C9—C10	−67.5 (3)	C19—O4—C21—C22	−178.9 (3)
C13—C8—C9—C10	54.3 (3)	C4—O1—C24—C23	176.0 (3)
N2—C9—C10—C11	−177.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3′···N2	0.85 (1)	1.77 (3)	2.550 (4)	152 (3)
O2—H2′···N1	0.84 (1)	1.85 (2)	2.584 (3)	144 (4)
O1W—H1B···O3	0.86 (5)	2.34 (7)	3.005 (5)	134 (8)
O1W—H1B···O4	0.86 (5)	2.38 (8)	3.052 (5)	135 (6)
C21—H21B···Cg	0.97	2.92	3.810 (4)	153

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3'···N2	0.850 (3)	1.77 (3)	2.550 (4)	152 (3)
O2—H2'···N1	0.840 (3)	1.85 (2)	2.584 (3)	144 (4)
O1W—H1B···O3	0.86 (5)	2.34 (7)	3.005 (5)	134 (8)
O1W—H1B···O4	0.86 (5)	2.38 (8)	3.052 (5)	135 (6)
C21—H21B···Cg	0.9700	2.92	3.810 (4)	153

Acknowledgements

We thank the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, for the diffraction measurements. MRPK, NM and SSS thank the Defence Research Development Organization, New Delhi, India, for financial support.

References

Ambili, K. U., Sreejith, S. S., Jacob, J. M., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2482. CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Franceschi, F., Solari, E., Floriani, C., Rosi, M., -Villa, A. C. & Rizzoli, C. (1999). Chem. Eur. J. 5, 708–721. CrossRef CAS Google Scholar
Hwang, C.-D., Hwang, D.-R. & Uang, B.-J. (1998). J. Org. Chem. 63, 6762–6763. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jones, R. D., Summerville, D. A. & Basolo, F. (1979). Chem. Rev. 79, 139–179. CrossRef CAS Web of Science Google Scholar
Popović, Z., Pavlović, G., Calogović, D. M., Roje, V. & Leban, I. (2002). J. Mol. Struct. 615, 23–31. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tümer, M. (2000). Synth. React. Inorg. Met. Org. Chem. 30, 1139–1158. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals 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 70| Part 2| February 2014| Pages o182-o183

doi:10.1107/S1600536814000713

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

(±)-trans-6,6′-Dieth­­oxy-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­­idene)]diphenol monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(±)-trans-6,6′-Diethoxy-2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol monohydrate