Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol

Tabatabaee, M.; Fotuhiardakani, M.R.; Lough, A.J.

doi:10.1107/S1600536811020599

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1579-o1580

doi:10.1107/S1600536811020599

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Redetermination of 6,6′-dimethoxy-2,2′-[hexane-1,6-diylbis(nitrilodimethylidyne)]diphenol

M. Tabatabaee,^a ^* M. R. Fotuhiardakani ^a and Alan J. Lough ^b

^aDepartment of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran, and ^bDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: tabatabaee45m@yahoo.com

(Received 20 May 2011; accepted 29 May 2011; online 4 June 2011)

The title compound, C₂₂H₂₈N₂O₄, contains two independent centrosymmetric molecules (A and B). In the previous structure determination [Xia et al. (2007 ). Acta Cryst. E63, o259] both A and B were modelled as neutral molecules with the H atoms of the the O—H groups included in calculated positions. In this redetermination, the transferrable H atoms were located in difference maps and freely refined, indicating that one molecule (A) crystallizes in the neutral (nonzwitterionic) form and the other in the zwitterionic form, namely 6,6′-dimethoxy-2,2′-[hexane-1,6-diylbis(nitrilodimethylidyne)]diphenol–6,6′-dimethoxy-2,2′-[hexane-1,6-diylbis(nitriliodimethylidyne)]diphenolate (1/1). This finding is supported by significant differences in the C—O(H) (A) and C—O⁻ (B) bond lengths. In the crystal, the zwitterionic molecules (B) are involved in intermolecular N—H⋯O hydrogen bonds forming one-dimensional chains along [001]. Each independent molecule forms an intramolecular O—H⋯N (A) or N—H⋯O (B) hydrogen bond. In molecule B, one of the –CH₂– groups is disordered over two sets of sites with refined occupancies of 0.659 (8) and 0.341 (8).

Related literature

For background to Schiff bases as ligands, see: Ray et al. (2008 ); Tabatabaee et al. (2006 ). For the previous crystal structure of the title compound, see: Xia et al. (2007).

Experimental

Crystal data

C₂₂H₂₈N₂O₄
M_r = 384.46
Monoclinic, P 2₁ /c
a = 21.2660 (4) Å
b = 8.4296 (3) Å
c = 11.1215 (9) Å
β = 92.3440 (17)°
V = 1992.02 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.32 × 0.24 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.871, T_max = 0.990
9462 measured reflections
3462 independent reflections
1976 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.247
S = 1.05
3462 reflections
268 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1O⋯N1A	1.05 (5)	1.64 (5)	2.575 (4)	146 (4)
N1B—H2O⋯O1B	0.98 (5)	1.87 (5)	2.655 (4)	136 (4)
N1B—H2O⋯O1Bⁱ	0.98 (5)	2.31 (5)	2.976 (4)	125 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO–SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020599/hb5887sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020599/hb5887Isup2.hkl

checkCIF report

Comment top

Schiff base ligands of salicylaldehyde and diamine can act as tetradentate ligands and provide suitable coordination modes for transition metal ions (Ray et al. 2008). As part of our studies on Schiff bases and their complexes (Tabatabaee et al., 2006) we have re-determined the crystal structure of the title compound, (I).

The title compound contains two centrosymmetric independent molecules [A and B] (see Figs. 1 and 2). In the original crystal structure determination (Xia et al., 2007) the H atoms of the the N—H groups were included in calculated positions. In the current determination we refined the positional and isotropic displacement parameters of these H atoms which shows that one independent molecule [B], crystallizes in the zwitterionic form. This finding is supported by the significant differnces in the distances of the C6A—O1A and C6B—O1B bonds. The zwitterionic molecules [B] are involved in intermolecular N—H···O hydrogen bonds forming one-dimensional chains along [001] (see Fig. 3). Each independent molecule forms an intramolecular O—H···N (A) or N—H···O (B) hydrogen bond. In molecule B one of the –CH₂– groups is disordeered over two sets of sites (Fig. 2) with refined occupancies 0.659 (8) and 0.341 (8). In one of the independent molecules in the original determination (Xia et al., 2007) the anisotropic displacement ellipsoids of the C atoms in the hexyl chain are significantly larger than in the other.

Related literature top

For background to Schiff bases as ligands, see: Ray et al. (2008); Tabatabaee et al. (2006). For the previous crystal structure of the title compound, see: Xia et al. (2007).

Experimental top

All purchased chemicals were of reagent grade and used without further purification. A solution of hexamethylenediamine (1.162 g, 10 mmol) in EtOH (30 ml) was treated with 2-hydroxy-3-methoxybezaldehyde (3.043 g, 20 mmol) and the resulting mixture was acidified with 37% hydrochloric acid (10 drops). The reaction mixture was refluxed for 6 h. The progress of the reaction was monitored by TLC using hexane/ethylacetate (1/2) as eluent. After completion of reaction, the solid residue was filtered and washed with cold ethanol (10 ml). The filtrate was dissolved in CH₃OH and kept at 277 K. Orange blocks of (I) were obtained after a few days (yield 82%).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecule A showing 30% probability ellipsoids. An intramolecular hydrogen bond is shown with a dashed line. Symmetry code: (a) -x, -y + 2, -z + 1.
	Fig. 2. Molecule B showing 30% probability ellipsoids. An intramolecular hydrogen bond and the disorder is shown with a dashed lines. Symmetry code: (b) -x + 1, -y + 1, -z.
	Fig. 3. Part of the crystal structure with intermolecular hydrogen bonds shown as dashed lines. Only molecule B is shown but the disorder is not shown.

6,6'-dimethoxy-2,2'-[hexane-1,6-diylbis(nitrilodimethylidyne)]diphenol– 6,6'-dimethoxy-2,2'-[hexane-1,6-diylbis(nitriliodimethylidyne)]diphenolate (1/1) top

Crystal data top

C₂₂H₂₈N₂O₄	F(000) = 824
M_r = 384.46	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8545 reflections
a = 21.2660 (4) Å	θ = 2.6–27.5°
b = 8.4296 (3) Å	µ = 0.09 mm⁻¹
c = 11.1215 (9) Å	T = 150 K
β = 92.3440 (17)°	Block, orange
V = 1992.02 (18) Å³	0.32 × 0.24 × 0.18 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3462 independent reflections
Radiation source: fine-focus sealed tube	1976 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ϕ scans and ω scans with κ offsets	h = −20→25
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −9→9
T_min = 0.871, T_max = 0.990	l = −13→13
9462 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.247	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.1195P)² + 1.1215P] where P = (F_o² + 2F_c²)/3
3462 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.35 e Å⁻³
6 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₂H₂₈N₂O₄	V = 1992.02 (18) Å³
M_r = 384.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.2660 (4) Å	µ = 0.09 mm⁻¹
b = 8.4296 (3) Å	T = 150 K
c = 11.1215 (9) Å	0.32 × 0.24 × 0.18 mm
β = 92.3440 (17)°

Data collection top

Nonius KappaCCD diffractometer	3462 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1976 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.990	R_int = 0.042
9462 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	6 restraints
wR(F²) = 0.247	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.35 e Å⁻³
3462 reflections	Δρ_min = −0.39 e Å⁻³
268 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	Occ. (<1)
O1A	0.16093 (12)	0.6165 (3)	0.8801 (3)	0.0706 (8)
O2A	0.22393 (14)	0.4763 (4)	1.0569 (3)	0.0894 (10)
N1A	0.08999 (14)	0.5965 (3)	0.6874 (3)	0.0660 (9)
C1A	0.00468 (18)	0.9101 (4)	0.4966 (3)	0.0648 (10)
H1A1	−0.0371	0.8580	0.4966	0.078*
H1A2	0.0238	0.8842	0.4193	0.078*
C2A	0.04555 (17)	0.8419 (4)	0.5979 (3)	0.0655 (11)
H2AA	0.0261	0.8645	0.6754	0.079*
H2AB	0.0872	0.8943	0.5991	0.079*
C3A	0.0543 (2)	0.6646 (4)	0.5851 (4)	0.0741 (11)
H3AA	0.0125	0.6131	0.5778	0.089*
H3AB	0.0765	0.6426	0.5105	0.089*
C4A	0.08887 (18)	0.4456 (4)	0.7018 (3)	0.0650 (11)
H4AA	0.0648	0.3830	0.6458	0.078*
C5A	0.12288 (17)	0.3671 (4)	0.8002 (3)	0.0624 (10)
C6A	0.15779 (17)	0.4555 (4)	0.8857 (4)	0.0653 (11)
C7A	0.19146 (19)	0.3778 (5)	0.9810 (4)	0.0726 (11)
C8A	0.1903 (2)	0.2153 (5)	0.9877 (4)	0.0789 (12)
H8AA	0.2136	0.1628	1.0506	0.095*
C9A	0.1552 (2)	0.1265 (5)	0.9028 (4)	0.0817 (13)
H9AA	0.1546	0.0141	0.9089	0.098*
C10A	0.12156 (19)	0.2003 (4)	0.8105 (4)	0.0738 (12)
H10A	0.0974	0.1390	0.7538	0.089*
C11A	0.2637 (2)	0.4050 (6)	1.1506 (4)	0.1000 (15)
H11A	0.2848	0.4887	1.1984	0.150*
H11B	0.2954	0.3379	1.1142	0.150*
H11C	0.2380	0.3403	1.2028	0.150*
O1B	0.43692 (11)	0.4470 (4)	0.56095 (19)	0.0886 (11)
O2B	0.38305 (12)	0.3658 (4)	0.7646 (2)	0.0954 (11)
N1B	0.43025 (14)	0.5949 (5)	0.3500 (3)	0.0882 (13)
C1B	0.4797 (2)	0.5579 (8)	0.0265 (4)	0.114 (2)
H1B1	0.4393	0.5657	−0.0206	0.137*	0.659 (8)
H1B2	0.5001	0.6636	0.0282	0.137*	0.659 (8)
C2B	0.4685 (3)	0.5001 (9)	0.1557 (4)	0.099 (2)	0.659 (8)
H2B1	0.4326	0.4251	0.1547	0.119*	0.659 (8)
H2B2	0.5063	0.4440	0.1885	0.119*	0.659 (8)
C3B	0.4545 (2)	0.6411 (7)	0.2340 (3)	0.1071 (19)
H3B1	0.4935	0.7037	0.2480	0.128*	0.659 (8)
H3B2	0.4233	0.7099	0.1911	0.128*	0.659 (8)
H1C1	0.4538	0.6014	−0.0417	0.137*	0.341 (8)
H1C2	0.5080	0.6450	0.0539	0.137*	0.341 (8)
C2C	0.4343 (5)	0.5349 (17)	0.1277 (7)	0.099 (2)	0.341 (8)
H2C1	0.4345	0.4224	0.1534	0.119*	0.341 (8)
H2C2	0.3910	0.5628	0.0989	0.119*	0.341 (8)
H3C1	0.5011	0.6418	0.2414	0.128*	0.341 (8)
H3C2	0.4406	0.7509	0.2158	0.128*	0.341 (8)
C4B	0.37526 (17)	0.6398 (6)	0.3855 (4)	0.0861 (14)
H4BA	0.3505	0.7030	0.3311	0.103*
C5B	0.34914 (16)	0.6039 (6)	0.4962 (4)	0.0798 (13)
C6B	0.38292 (16)	0.5038 (6)	0.5797 (3)	0.0772 (12)
C7B	0.35069 (17)	0.4685 (6)	0.6899 (4)	0.0813 (13)
C8B	0.2942 (2)	0.5351 (6)	0.7126 (5)	0.0921 (15)
H8BA	0.2747	0.5107	0.7857	0.110*
C9B	0.2641 (2)	0.6386 (6)	0.6309 (6)	0.1033 (18)
H9BA	0.2254	0.6868	0.6500	0.124*
C10B	0.29012 (18)	0.6703 (6)	0.5244 (5)	0.0971 (15)
H10B	0.2687	0.7376	0.4679	0.116*
C11B	0.3548 (2)	0.3244 (8)	0.8761 (3)	0.1133 (19)
H11D	0.3812	0.2460	0.9193	0.170*
H11E	0.3129	0.2795	0.8589	0.170*
H11F	0.3511	0.4196	0.9259	0.170*
H1O	0.131 (2)	0.652 (5)	0.808 (4)	0.103 (16)*
H2O	0.455 (2)	0.543 (5)	0.415 (4)	0.110 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0662 (16)	0.0594 (16)	0.0884 (19)	−0.0094 (12)	0.0296 (15)	−0.0089 (13)
O2A	0.088 (2)	0.092 (2)	0.090 (2)	−0.0109 (17)	0.0239 (17)	−0.0061 (17)
N1A	0.0681 (19)	0.0525 (19)	0.080 (2)	0.0005 (15)	0.0308 (17)	−0.0061 (15)
C1A	0.071 (2)	0.0507 (19)	0.075 (2)	−0.0066 (17)	0.040 (2)	−0.0103 (17)
C2A	0.070 (2)	0.046 (2)	0.083 (3)	−0.0049 (17)	0.036 (2)	−0.0073 (18)
C3A	0.087 (3)	0.055 (2)	0.081 (3)	0.003 (2)	0.025 (2)	−0.011 (2)
C4A	0.069 (2)	0.053 (2)	0.075 (3)	−0.0054 (18)	0.042 (2)	−0.0106 (18)
C5A	0.066 (2)	0.054 (2)	0.069 (2)	−0.0058 (18)	0.0380 (19)	−0.0024 (19)
C6A	0.063 (2)	0.054 (2)	0.082 (3)	−0.0068 (18)	0.042 (2)	−0.005 (2)
C7A	0.069 (2)	0.074 (3)	0.078 (3)	−0.006 (2)	0.041 (2)	0.000 (2)
C8A	0.080 (3)	0.074 (3)	0.086 (3)	0.003 (2)	0.044 (2)	0.009 (2)
C9A	0.101 (3)	0.061 (2)	0.087 (3)	−0.002 (2)	0.052 (3)	0.011 (2)
C10A	0.086 (3)	0.056 (2)	0.083 (3)	−0.010 (2)	0.047 (2)	−0.008 (2)
C11A	0.099 (3)	0.130 (4)	0.073 (3)	0.002 (3)	0.025 (3)	0.015 (3)
O1B	0.0384 (13)	0.189 (3)	0.0393 (13)	0.0166 (16)	0.0074 (10)	0.0170 (16)
O2B	0.0551 (15)	0.188 (3)	0.0445 (14)	−0.0037 (18)	0.0181 (12)	0.0093 (17)
N1B	0.0439 (18)	0.179 (4)	0.0413 (17)	0.000 (2)	−0.0026 (13)	0.026 (2)
C1B	0.060 (3)	0.224 (6)	0.060 (3)	0.009 (3)	0.021 (2)	0.022 (3)
C2B	0.041 (4)	0.201 (7)	0.057 (3)	0.025 (4)	0.016 (3)	0.030 (4)
C3B	0.067 (3)	0.215 (6)	0.038 (2)	−0.013 (3)	−0.0081 (18)	0.040 (3)
C1C	0.060 (3)	0.224 (6)	0.060 (3)	0.009 (3)	0.021 (2)	0.022 (3)
C2C	0.041 (4)	0.201 (7)	0.057 (3)	0.025 (4)	0.016 (3)	0.030 (4)
C3C	0.067 (3)	0.215 (6)	0.038 (2)	−0.013 (3)	−0.0081 (18)	0.040 (3)
C4B	0.041 (2)	0.139 (4)	0.077 (3)	−0.009 (2)	−0.0144 (19)	0.023 (3)
C5B	0.0350 (18)	0.129 (4)	0.076 (3)	−0.004 (2)	0.0069 (18)	0.014 (2)
C6B	0.0396 (19)	0.140 (4)	0.053 (2)	0.004 (2)	0.0116 (16)	0.001 (2)
C7B	0.045 (2)	0.139 (4)	0.060 (2)	−0.009 (2)	0.0191 (18)	−0.005 (2)
C8B	0.065 (3)	0.108 (3)	0.107 (4)	−0.014 (3)	0.046 (3)	−0.012 (3)
C9B	0.053 (2)	0.097 (3)	0.164 (5)	−0.011 (2)	0.054 (3)	−0.005 (3)
C10B	0.047 (2)	0.101 (3)	0.143 (4)	−0.005 (2)	0.018 (3)	0.015 (3)
C11B	0.086 (3)	0.205 (6)	0.051 (2)	−0.024 (3)	0.032 (2)	0.007 (3)

Geometric parameters (Å, º) top

O1A—C6A	1.360 (4)	O2B—C7B	1.366 (5)
O1A—H1O	1.05 (5)	O2B—C11B	1.443 (4)
O2A—C7A	1.353 (5)	N1B—C4B	1.306 (5)
O2A—C11A	1.446 (5)	N1B—C3B	1.462 (5)
N1A—C4A	1.283 (4)	N1B—H2O	0.98 (5)
N1A—C3A	1.459 (5)	C1B—C1Bⁱⁱ	1.443 (11)
C1A—C2A	1.508 (5)	C1B—C2B	1.545 (6)
C1A—C1Aⁱ	1.531 (7)	C1B—H1B1	0.9900
C1A—H1A1	0.9900	C1B—H1B2	0.9900
C1A—H1A2	0.9900	C2B—C3B	1.510 (6)
C2A—C3A	1.513 (5)	C2B—H2B1	0.9900
C2A—H2AA	0.9900	C2B—H2B2	0.9900
C2A—H2AB	0.9900	C3B—H3B1	0.9900
C3A—H3AA	0.9900	C3B—H3B2	0.9900
C3A—H3AB	0.9900	C2C—H2C1	0.9900
C4A—C5A	1.447 (5)	C2C—H2C2	0.9900
C4A—H4AA	0.9500	C4B—C5B	1.404 (6)
C5A—C6A	1.398 (5)	C4B—H4BA	0.9500
C5A—C10A	1.411 (5)	C5B—C10B	1.421 (6)
C6A—C7A	1.415 (6)	C5B—C6B	1.427 (6)
C7A—C8A	1.372 (6)	C6B—C7B	1.459 (5)
C8A—C9A	1.397 (6)	C7B—C8B	1.359 (6)
C8A—H8AA	0.9500	C8B—C9B	1.396 (7)
C9A—C10A	1.376 (6)	C8B—H8BA	0.9500
C9A—H9AA	0.9500	C9B—C10B	1.354 (7)
C10A—H10A	0.9500	C9B—H9BA	0.9500
C11A—H11A	0.9800	C10B—H10B	0.9500
C11A—H11B	0.9800	C11B—H11D	0.9800
C11A—H11C	0.9800	C11B—H11E	0.9800
O1B—C6B	1.269 (4)	C11B—H11F	0.9800

C6A—O1A—H1O	107 (3)	C4B—N1B—C3B	122.9 (4)
C7A—O2A—C11A	117.6 (4)	C4B—N1B—H2O	111 (3)
C4A—N1A—C3A	118.4 (3)	C3B—N1B—H2O	125 (3)
C2A—C1A—C1Aⁱ	114.3 (4)	C1Bⁱⁱ—C1B—C2B	106.5 (6)
C2A—C1A—H1A1	108.7	C1Bⁱⁱ—C1B—H1B1	110.4
C1Aⁱ—C1A—H1A1	108.7	C2B—C1B—H1B1	110.4
C2A—C1A—H1A2	108.7	C1Bⁱⁱ—C1B—H1B2	110.4
C1Aⁱ—C1A—H1A2	108.7	C2B—C1B—H1B2	110.4
H1A1—C1A—H1A2	107.6	H1B1—C1B—H1B2	108.6
C1A—C2A—C3A	112.1 (3)	C3B—C2B—C1B	109.3 (5)
C1A—C2A—H2AA	109.2	C3B—C2B—H2B1	109.8
C3A—C2A—H2AA	109.2	C1B—C2B—H2B1	109.8
C1A—C2A—H2AB	109.2	C3B—C2B—H2B2	109.8
C3A—C2A—H2AB	109.2	C1B—C2B—H2B2	109.8
H2AA—C2A—H2AB	107.9	H2B1—C2B—H2B2	108.3
N1A—C3A—C2A	112.2 (3)	N1B—C3B—C2B	112.6 (5)
N1A—C3A—H3AA	109.2	N1B—C3B—H3B1	109.1
C2A—C3A—H3AA	109.2	C2B—C3B—H3B1	109.1
N1A—C3A—H3AB	109.2	N1B—C3B—H3B2	109.1
C2A—C3A—H3AB	109.2	C2B—C3B—H3B2	109.1
H3AA—C3A—H3AB	107.9	H3B1—C3B—H3B2	107.8
N1A—C4A—C5A	122.5 (4)	H2C1—C2C—H2C2	108.3
N1A—C4A—H4AA	118.8	N1B—C4B—C5B	126.5 (4)
C5A—C4A—H4AA	118.8	N1B—C4B—H4BA	116.8
C6A—C5A—C10A	119.2 (4)	C5B—C4B—H4BA	116.8
C6A—C5A—C4A	120.4 (3)	C4B—C5B—C10B	119.6 (4)
C10A—C5A—C4A	120.4 (4)	C4B—C5B—C6B	119.4 (3)
O1A—C6A—C5A	121.8 (4)	C10B—C5B—C6B	121.0 (4)
O1A—C6A—C7A	118.2 (4)	O1B—C6B—C5B	123.4 (3)
C5A—C6A—C7A	120.1 (3)	O1B—C6B—C7B	121.4 (4)
O2A—C7A—C8A	126.0 (5)	C5B—C6B—C7B	115.2 (3)
O2A—C7A—C6A	114.4 (4)	C8B—C7B—O2B	125.2 (4)
C8A—C7A—C6A	119.6 (4)	C8B—C7B—C6B	121.4 (4)
C7A—C8A—C9A	120.5 (4)	O2B—C7B—C6B	113.4 (3)
C7A—C8A—H8AA	119.7	C7B—C8B—C9B	121.5 (4)
C9A—C8A—H8AA	119.7	C7B—C8B—H8BA	119.2
C10A—C9A—C8A	120.6 (4)	C9B—C8B—H8BA	119.2
C10A—C9A—H9AA	119.7	C10B—C9B—C8B	120.0 (4)
C8A—C9A—H9AA	119.7	C10B—C9B—H9BA	120.0
C9A—C10A—C5A	120.0 (4)	C8B—C9B—H9BA	120.0
C9A—C10A—H10A	120.0	C9B—C10B—C5B	120.8 (5)
C5A—C10A—H10A	120.0	C9B—C10B—H10B	119.6
O2A—C11A—H11A	109.5	C5B—C10B—H10B	119.6
O2A—C11A—H11B	109.5	O2B—C11B—H11D	109.5
H11A—C11A—H11B	109.5	O2B—C11B—H11E	109.5
O2A—C11A—H11C	109.5	H11D—C11B—H11E	109.5
H11A—C11A—H11C	109.5	O2B—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11D—C11B—H11F	109.5
C7B—O2B—C11B	117.3 (3)	H11E—C11B—H11F	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···N1A	1.05 (5)	1.64 (5)	2.575 (4)	146 (4)
N1B—H2O···O1B	0.98 (5)	1.87 (5)	2.655 (4)	136 (4)
N1B—H2O···O1Bⁱⁱⁱ	0.98 (5)	2.31 (5)	2.976 (4)	125 (4)

Symmetry code: (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₈N₂O₄
M_r	384.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	21.2660 (4), 8.4296 (3), 11.1215 (9)
β (°)	92.3440 (17)
V (Å³)	1992.02 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.24 × 0.18

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.871, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	9462, 3462, 1976
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.247, 1.05
No. of reflections	3462
No. of parameters	268
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.39

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···N1A	1.05 (5)	1.64 (5)	2.575 (4)	146 (4)
N1B—H2O···O1B	0.98 (5)	1.87 (5)	2.655 (4)	136 (4)
N1B—H2O···O1Bⁱ	0.98 (5)	2.31 (5)	2.976 (4)	125 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This research was supported by the Yazd Branch, Islamic Azad University, Yazd, Iran. AJL thanks NSERC Canada for funding.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Ray, A., Banerjee, S., Rosair, G. M., Gramlich, V. & Mitra, S. (2008). Struct. Chem. 19, 459–465 CrossRef CAS 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
Tabatabaee, M., Ghassemzadeh, M., Zaradi, B. & Neumüller, B. (2006). Z. Naturforsh. Teil B, 61, 1421–1425. CAS Google Scholar
Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, o259–o261. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Pages o1579-o1580

doi:10.1107/S1600536811020599

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

Redetermination of 6,6′-dimeth­­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­di­methyl­­idyne)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Redetermination of 6,6′-dimethoxy-2,2′-[hexane-1,6-diylbis(nitrilodimethylidyne)]diphenol