2-[(E)-({3-[(E)-(2-Hy­droxy­benzyl­idene)amino­meth­yl]-1,4-dioxaspiro­[4.5]decan-2-yl}meth­yl)imino­meth­yl]phenol

Jiang, Y.; Wang, L.; Bian, J.; Du, X.; Sun, X.

doi:10.1107/S1600536812029182

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2296

https://doi.org/10.1107/S1600536812029182

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2-[(E)-({3-[(E)-(2-Hydroxybenzylidene)aminomethyl]-1,4-dioxaspiro[4.5]decan-2-yl}methyl)iminomethyl]phenol

Yan Jiang,^a Lili Wang,^a Jing Bian,^a Xiaoying Du ^a and Xiaoqiang Sun ^a ^*

^aKey Laboratory of Fine Chemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
^*Correspondence e-mail: erliwanglili@163.com

(Received 14 June 2012; accepted 27 June 2012; online 30 June 2012)

In the title compound, C₂₄H₂₈N₂O₄, the dioxalane ring has an envelope conformation. The cyclohexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 72.5 (3)°. The molecular conformation is stabilized by two intramolecular O—H⋯N hydrogen-bonding interactions with an S(6) graph-set motif. The crystal structure is stabilized by van der Waals interactions.

Related literature

For the synthesis, see: Gan (2008 ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₈N₂O₄
M_r = 408.48
Monoclinic, P 2₁
a = 5.7443 (8) Å
b = 21.558 (3) Å
c = 9.0075 (11) Å
β = 95.074 (6)°
V = 1111.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.984, T_max = 0.988
6560 measured reflections
2102 independent reflections
1522 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.169
S = 1.01
2102 reflections
285 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.91	2.561 (5)	135
O4—H4⋯N1	0.82 (8)	1.83 (8)	2.601 (6)	157 (8)

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029182/bx2417sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029182/bx2417Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029182/bx2417Isup3.cml

checkCIF report

Comment top

Multidentate and chiral C₂-symmetric ligands have attracted considerable interest, however, the number of chiral precursors available from nature is seriously limited. Gan, (2008) have reported some similar C2-symmetric tartaric acid derivatives which have ability to metal coordination and effect to catalytic Henry reaction.We have undertaken the X-ray crystal-structure determination of (I) in order to establish its molecular conformation and relative stereochemistry. We are not able to determine the absolute stereochemistry by X-ray methods. We report here the synthesis and the crystal structure of the title compound based on L-tartaric acid. The dioxalane ring has an envelope conformation.(Q2=0.291 (5)Å, φ₂ = 286.4 (10)°. The cyclohexane ring adopt chair conformation (Q_T= 0.560 (6) Å, θ= 175.4 (6)°, φ₂ = 176.0 (8)° (Cremer & Pople, 1975). The dihedral angle between the two phenyl rings is 72.5 (3)°. The molecular conformation is stabilized by two intramolecular O—H···N hydrogen-bond interaction with graph-set motif S(6), (Bernstein et al., 1995) .The crystal structure is stabilized by van der Waals interactions. The bond lengths and angles are within normal ranges (Allen et al., 1987).

Related literature top

For the synthesis, see: Gan (2008). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound, (I) was prepared by a method reported by (Gan, 2008).To a solution of 2-hydroxybenzaldehyde(1.22 g, 10 mmol) in ethanol (15 ml), (2S,3S)-1,4-dioxaspiro[4.5]decane-2,3-diyldimethanamine(1 g, 5 mmol) dissolved in methanol(10 ml) was added. The mixture was refluxed for 2 h to complete the reaction and then cooled at room temperature. The compound was recrystallized from ethanol to afford a yellow solid (1.3 g, 63.7% yield, m.p. 360.45–361.25 K). Single crystal suitable for X-ray diffraction were also obtained by evaporation of an ethanol solution. The crystals were obtained by dissolving (I) (0.5 g, 1.22 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Structure description top

For the synthesis, see: Gan (2008). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

Figures top

Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The S(6) motifs is shows as dashed lines.

2-[(E)-({3-[(E)-(2-Hydroxybenzylidene)aminomethyl]- 1,4-dioxaspiro[4.5]decan-2-yl}methyl)iminomethyl]phenol top

Crystal data top

C₂₄H₂₈N₂O₄	F(000) = 436
M_r = 408.48	D_x = 1.221 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1658 reflections
a = 5.7443 (8) Å	θ = 2.3–20.6°
b = 21.558 (3) Å	µ = 0.08 mm⁻¹
c = 9.0075 (11) Å	T = 296 K
β = 95.074 (6)°	Block, colourless
V = 1111.1 (2) Å³	0.20 × 0.18 × 0.15 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	1522 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.5°, θ_min = 1.9°
ω/2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −26→25
T_min = 0.984, T_max = 0.988	l = −9→10
6560 measured reflections	3 standard reflections every 200 reflections
2102 independent reflections	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.1156P)²] where P = (F_o² + 2F_c²)/3
2102 reflections	(Δ/σ)_max = 0.002
285 parameters	Δρ_max = 0.57 e Å⁻³
13 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₂₈N₂O₄	V = 1111.1 (2) Å³
M_r = 408.48	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.7443 (8) Å	µ = 0.08 mm⁻¹
b = 21.558 (3) Å	T = 296 K
c = 9.0075 (11) Å	0.20 × 0.18 × 0.15 mm
β = 95.074 (6)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1522 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.984, T_max = 0.988	3 standard reflections every 200 reflections
6560 measured reflections	intensity decay: 1%
2102 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	13 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.57 e Å⁻³
2102 reflections	Δρ_min = −0.33 e Å⁻³
285 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
O2	0.7032 (5)	0.0442 (2)	0.2755 (3)	0.0579 (8)
N1	0.4452 (7)	0.19135 (19)	0.6142 (4)	0.0587 (10)
N2	0.7647 (7)	−0.01611 (17)	0.5564 (4)	0.0515 (9)
O3	0.3731 (6)	−0.0730 (2)	0.5143 (5)	0.0793 (11)
H3	0.4865	−0.0579	0.4784	0.119*
O4	0.1145 (9)	0.1775 (2)	0.7908 (5)	0.0814 (12)
C7	0.2202 (10)	0.2762 (2)	0.6925 (5)	0.0613 (13)
C19	0.8210 (8)	−0.0504 (2)	0.6661 (5)	0.0573 (12)
H19	0.9640	−0.0443	0.7209	0.069*
C24	0.7982 (8)	0.0768 (2)	0.4043 (5)	0.0536 (11)
H24	0.9080	0.1086	0.3760	0.064*
C23	0.5846 (8)	0.1074 (2)	0.4606 (5)	0.0560 (11)
H23	0.5118	0.0790	0.5278	0.067*
C14	0.4466 (9)	−0.1094 (2)	0.6303 (6)	0.0597 (12)
C13	0.6671 (8)	−0.0998 (2)	0.7097 (5)	0.0587 (12)
C8	0.0807 (9)	0.2405 (2)	0.7772 (5)	0.0601 (13)
C20	0.9224 (7)	0.0312 (2)	0.5111 (5)	0.0584 (12)
H20A	1.0488	0.0118	0.4636	0.070*
H20B	0.9898	0.0533	0.5985	0.070*
C21	0.4048 (11)	0.2486 (3)	0.6123 (6)	0.0667 (14)
H21	0.4955	0.2744	0.5579	0.080*
C22	0.6410 (11)	0.1678 (3)	0.5390 (7)	0.0675 (14)
C4	0.5053 (8)	0.0777 (3)	0.2129 (5)	0.0636 (12)
C1	0.4141 (10)	0.0380 (3)	−0.0967 (5)	0.0721 (14)
H1A	0.4493	0.0136	−0.1824	0.087*
H1B	0.2772	0.0630	−0.1254	0.087*
C10	−0.1293 (12)	0.3299 (3)	0.8382 (8)	0.0847 (19)
H10	−0.2521	0.3474	0.8844	0.102*
C2	0.3642 (11)	−0.0043 (3)	0.0280 (6)	0.0752 (16)
H2A	0.4974	−0.0312	0.0527	0.090*
H2B	0.2301	−0.0301	−0.0024	0.090*
C16	0.3780 (13)	−0.1954 (3)	0.7878 (8)	0.0859 (18)
H16	0.2854	−0.2288	0.8112	0.103*
C12	0.1847 (16)	0.3400 (3)	0.6869 (7)	0.096 (2)
H12	0.2806	0.3647	0.6336	0.115*
C15	0.3060 (11)	−0.1579 (3)	0.6720 (7)	0.0732 (15)
H15	0.1612	−0.1646	0.6198	0.088*
C6	0.6157 (11)	0.0792 (3)	−0.0503 (6)	0.0833 (18)
H6A	0.6461	0.1062	−0.1326	0.100*
H6B	0.7540	0.0541	−0.0260	0.100*
C9	−0.0925 (11)	0.2673 (3)	0.8512 (7)	0.0775 (16)
H9	−0.1835	0.2433	0.9094	0.093*
C18	0.7323 (12)	−0.1387 (4)	0.8281 (7)	0.0866 (19)
H18	0.8785	−0.1336	0.8798	0.104*
C3	0.3153 (9)	0.0337 (3)	0.1633 (6)	0.0712 (14)
H3A	0.1719	0.0569	0.1403	0.085*
H3B	0.2906	0.0057	0.2447	0.085*
C5	0.5689 (10)	0.1184 (3)	0.0836 (6)	0.0738 (15)
H5A	0.4417	0.1469	0.0562	0.089*
H5B	0.7069	0.1426	0.1149	0.089*
C11	0.0057 (15)	0.3675 (3)	0.7606 (7)	0.094 (2)
H11	−0.0195	0.4101	0.7565	0.113*
C17	0.5884 (14)	−0.1845 (4)	0.8717 (8)	0.102 (2)
H17	0.6310	−0.2080	0.9564	0.122*
H22A	0.682 (10)	0.196 (3)	0.479 (7)	0.075 (18)*
H22B	0.802 (9)	0.158 (2)	0.614 (6)	0.067 (15)*
H4	0.237 (13)	0.175 (4)	0.752 (9)	0.10 (3)*
O1	0.4339 (7)	0.1163 (3)	0.3301 (4)	0.0890 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0607 (18)	0.0631 (18)	0.0497 (17)	0.0170 (16)	0.0035 (13)	−0.0074 (15)
N1	0.069 (2)	0.052 (2)	0.055 (2)	0.007 (2)	0.0034 (18)	−0.0128 (18)
N2	0.050 (2)	0.052 (2)	0.051 (2)	0.0082 (18)	0.0011 (16)	0.0039 (17)
O3	0.063 (2)	0.080 (2)	0.091 (3)	0.000 (2)	−0.017 (2)	0.024 (2)
O4	0.080 (3)	0.057 (2)	0.110 (3)	0.001 (2)	0.022 (2)	−0.005 (2)
C7	0.089 (3)	0.051 (3)	0.043 (2)	0.016 (3)	0.004 (2)	−0.001 (2)
C19	0.049 (2)	0.072 (3)	0.051 (3)	0.012 (2)	0.005 (2)	−0.002 (2)
C24	0.049 (2)	0.061 (3)	0.051 (2)	0.006 (2)	0.0059 (18)	−0.003 (2)
C23	0.054 (2)	0.065 (3)	0.047 (2)	0.012 (2)	−0.0030 (18)	−0.014 (2)
C14	0.059 (3)	0.056 (3)	0.065 (3)	0.019 (2)	0.011 (2)	0.003 (2)
C13	0.053 (3)	0.071 (3)	0.053 (2)	0.017 (2)	0.010 (2)	0.005 (2)
C8	0.063 (3)	0.057 (3)	0.059 (3)	0.000 (2)	−0.004 (2)	−0.010 (2)
C20	0.047 (2)	0.065 (3)	0.062 (3)	0.004 (2)	−0.001 (2)	0.003 (2)
C21	0.093 (4)	0.054 (3)	0.055 (3)	0.002 (3)	0.017 (3)	0.000 (2)
C22	0.078 (4)	0.055 (3)	0.073 (4)	−0.001 (3)	0.021 (3)	−0.012 (3)
C4	0.059 (3)	0.081 (3)	0.049 (2)	0.021 (2)	−0.0022 (19)	−0.013 (2)
C1	0.090 (4)	0.077 (3)	0.050 (3)	0.010 (3)	0.003 (2)	−0.014 (3)
C10	0.078 (4)	0.091 (4)	0.082 (4)	0.032 (4)	−0.008 (3)	−0.024 (4)
C2	0.083 (4)	0.065 (3)	0.075 (4)	−0.010 (3)	−0.008 (3)	−0.007 (3)
C16	0.099 (5)	0.073 (4)	0.090 (4)	0.001 (4)	0.033 (4)	0.012 (3)
C12	0.152 (7)	0.070 (4)	0.069 (4)	0.035 (4)	0.027 (4)	0.015 (3)
C15	0.070 (3)	0.068 (3)	0.084 (4)	0.002 (3)	0.017 (3)	0.002 (3)
C6	0.087 (4)	0.106 (5)	0.058 (3)	−0.009 (4)	0.018 (3)	0.021 (3)
C9	0.068 (3)	0.079 (4)	0.087 (4)	−0.003 (3)	0.014 (3)	−0.016 (3)
C18	0.077 (4)	0.109 (5)	0.073 (4)	0.016 (4)	0.004 (3)	0.039 (4)
C3	0.062 (3)	0.091 (4)	0.060 (3)	−0.005 (3)	0.005 (2)	0.016 (3)
C5	0.089 (4)	0.054 (3)	0.074 (4)	−0.006 (3)	−0.014 (3)	0.004 (3)
C11	0.149 (7)	0.071 (4)	0.064 (3)	0.045 (4)	0.020 (4)	0.002 (3)
C17	0.098 (5)	0.120 (6)	0.089 (5)	0.015 (5)	0.021 (4)	0.048 (4)
O1	0.084 (2)	0.111 (3)	0.067 (2)	0.045 (2)	−0.0180 (17)	−0.0291 (19)

Geometric parameters (Å, º) top

O2—C4	1.420 (6)	C4—C3	1.485 (8)
O2—C24	1.424 (6)	C4—C5	1.528 (8)
N1—C21	1.257 (7)	C1—C6	1.490 (8)
N1—C22	1.455 (7)	C1—C2	1.494 (8)
N2—C19	1.253 (6)	C1—H1A	0.9700
N2—C20	1.447 (6)	C1—H1B	0.9700
O3—C14	1.344 (7)	C10—C11	1.357 (10)
O3—H3	0.8200	C10—C9	1.370 (9)
O4—C8	1.378 (8)	C10—H10	0.9300
O4—H4	0.82 (7)	C2—C3	1.515 (8)
C7—C8	1.387 (8)	C2—H2A	0.9700
C7—C12	1.389 (8)	C2—H2B	0.9700
C7—C21	1.461 (8)	C16—C15	1.355 (9)
C19—C13	1.460 (7)	C16—C17	1.388 (11)
C19—H19	0.9300	C16—H16	0.9300
C24—C20	1.509 (7)	C12—C11	1.404 (10)
C24—C23	1.519 (6)	C12—H12	0.9300
C24—H24	0.9800	C15—H15	0.9300
C23—O1	1.410 (6)	C6—C5	1.516 (8)
C23—C22	1.503 (7)	C6—H6A	0.9700
C23—H23	0.9800	C6—H6B	0.9700
C14—C15	1.393 (7)	C9—H9	0.9300
C14—C13	1.414 (7)	C18—C17	1.367 (10)
C13—C18	1.383 (8)	C18—H18	0.9300
C8—C9	1.373 (8)	C3—H3A	0.9700
C20—H20A	0.9700	C3—H3B	0.9700
C20—H20B	0.9700	C5—H5A	0.9700
C21—H21	0.9300	C5—H5B	0.9700
C22—H22A	0.86 (6)	C11—H11	0.9300
C22—H22B	1.12 (6)	C17—H17	0.9300
C4—O1	1.434 (6)

C4—O2—C24	107.9 (4)	C6—C1—H1A	109.6
C21—N1—C22	119.1 (5)	C2—C1—H1A	109.6
C19—N2—C20	121.0 (4)	C6—C1—H1B	109.6
C14—O3—H3	109.5	C2—C1—H1B	109.6
C8—O4—H4	98 (6)	H1A—C1—H1B	108.1
C8—C7—C12	118.6 (6)	C11—C10—C9	122.8 (7)
C8—C7—C21	121.7 (4)	C11—C10—H10	118.6
C12—C7—C21	119.7 (6)	C9—C10—H10	118.6
N2—C19—C13	121.5 (4)	C1—C2—C3	109.6 (5)
N2—C19—H19	119.3	C1—C2—H2A	109.7
C13—C19—H19	119.3	C3—C2—H2A	109.7
O2—C24—C20	108.8 (4)	C1—C2—H2B	109.7
O2—C24—C23	102.9 (3)	C3—C2—H2B	109.7
C20—C24—C23	114.8 (4)	H2A—C2—H2B	108.2
O2—C24—H24	110.0	C15—C16—C17	120.7 (6)
C20—C24—H24	110.0	C15—C16—H16	119.7
C23—C24—H24	110.0	C17—C16—H16	119.7
O1—C23—C22	111.3 (5)	C7—C12—C11	120.8 (7)
O1—C23—C24	103.6 (4)	C7—C12—H12	119.6
C22—C23—C24	112.7 (4)	C11—C12—H12	119.6
O1—C23—H23	109.7	C16—C15—C14	120.7 (6)
C22—C23—H23	109.7	C16—C15—H15	119.6
C24—C23—H23	109.7	C14—C15—H15	119.6
O3—C14—C15	119.9 (5)	C1—C6—C5	111.6 (5)
O3—C14—C13	120.9 (5)	C1—C6—H6A	109.3
C15—C14—C13	119.2 (5)	C5—C6—H6A	109.3
C18—C13—C14	118.1 (5)	C1—C6—H6B	109.3
C18—C13—C19	121.4 (5)	C5—C6—H6B	109.3
C14—C13—C19	120.5 (4)	H6A—C6—H6B	108.0
C9—C8—O4	118.3 (6)	C10—C9—C8	119.1 (7)
C9—C8—C7	120.8 (5)	C10—C9—H9	120.5
O4—C8—C7	120.9 (5)	C8—C9—H9	120.5
N2—C20—C24	111.5 (3)	C17—C18—C13	122.0 (6)
N2—C20—H20A	109.3	C17—C18—H18	119.0
C24—C20—H20A	109.3	C13—C18—H18	119.0
N2—C20—H20B	109.3	C4—C3—C2	113.8 (4)
C24—C20—H20B	109.3	C4—C3—H3A	108.8
H20A—C20—H20B	108.0	C2—C3—H3A	108.8
N1—C21—C7	122.3 (5)	C4—C3—H3B	108.8
N1—C21—H21	118.8	C2—C3—H3B	108.8
C7—C21—H21	118.8	H3A—C3—H3B	107.7
N1—C22—C23	112.2 (5)	C6—C5—C4	110.9 (4)
N1—C22—H22A	108 (4)	C6—C5—H5A	109.5
C23—C22—H22A	112 (4)	C4—C5—H5A	109.5
N1—C22—H22B	115 (3)	C6—C5—H5B	109.5
C23—C22—H22B	105 (3)	C4—C5—H5B	109.5
H22A—C22—H22B	105 (5)	H5A—C5—H5B	108.0
O2—C4—O1	105.9 (3)	C10—C11—C12	117.8 (6)
O2—C4—C3	109.6 (5)	C10—C11—H11	121.1
O1—C4—C3	110.0 (5)	C12—C11—H11	121.1
O2—C4—C5	110.9 (4)	C18—C17—C16	119.0 (6)
O1—C4—C5	109.3 (5)	C18—C17—H17	120.5
C3—C4—C5	110.9 (4)	C16—C17—H17	120.5
C6—C1—C2	110.4 (4)	C23—O1—C4	109.9 (4)

C20—N2—C19—C13	−177.8 (4)	C6—C1—C2—C3	57.8 (7)
C4—O2—C24—C20	152.8 (4)	C8—C7—C12—C11	−2.3 (10)
C4—O2—C24—C23	30.6 (5)	C21—C7—C12—C11	178.8 (6)
O2—C24—C23—O1	−29.2 (5)	C17—C16—C15—C14	3.0 (9)
C20—C24—C23—O1	−147.3 (5)	O3—C14—C15—C16	179.4 (6)
O2—C24—C23—C22	−149.6 (5)	C13—C14—C15—C16	0.4 (8)
C20—C24—C23—C22	92.2 (6)	C2—C1—C6—C5	−59.3 (7)
O3—C14—C13—C18	179.9 (5)	C11—C10—C9—C8	−3.3 (10)
C15—C14—C13—C18	−1.2 (8)	O4—C8—C9—C10	−179.6 (6)
O3—C14—C13—C19	−0.6 (7)	C7—C8—C9—C10	1.3 (9)
C15—C14—C13—C19	178.3 (4)	C14—C13—C18—C17	−1.6 (10)
N2—C19—C13—C18	178.1 (5)	C19—C13—C18—C17	178.9 (6)
N2—C19—C13—C14	−1.3 (7)	O2—C4—C3—C2	−70.3 (5)
C12—C7—C8—C9	1.4 (8)	O1—C4—C3—C2	173.6 (5)
C21—C7—C8—C9	−179.7 (5)	C5—C4—C3—C2	52.5 (6)
C12—C7—C8—O4	−177.6 (5)	C1—C2—C3—C4	−55.8 (6)
C21—C7—C8—O4	1.2 (8)	C1—C6—C5—C4	55.5 (6)
C19—N2—C20—C24	−165.4 (4)	O2—C4—C5—C6	70.8 (6)
O2—C24—C20—N2	−59.9 (5)	O1—C4—C5—C6	−172.8 (4)
C23—C24—C20—N2	54.8 (5)	C3—C4—C5—C6	−51.3 (6)
C22—N1—C21—C7	−176.3 (5)	C9—C10—C11—C12	2.4 (11)
C8—C7—C21—N1	0.8 (8)	C7—C12—C11—C10	0.5 (11)
C12—C7—C21—N1	179.6 (6)	C13—C18—C17—C16	5.0 (11)
C21—N1—C22—C23	−141.1 (5)	C15—C16—C17—C18	−5.7 (11)
O1—C23—C22—N1	73.8 (6)	C22—C23—O1—C4	139.1 (5)
C24—C23—C22—N1	−170.2 (4)	C24—C23—O1—C4	17.8 (6)
C24—O2—C4—O1	−20.3 (6)	O2—C4—O1—C23	0.5 (7)
C24—O2—C4—C3	−139.0 (4)	C3—C4—O1—C23	118.9 (5)
C24—O2—C4—C5	98.2 (4)	C5—C4—O1—C23	−119.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.91	2.561 (5)	135
O4—H4···N1	0.82 (8)	1.83 (8)	2.601 (6)	157 (8)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈N₂O₄
M_r	408.48
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	5.7443 (8), 21.558 (3), 9.0075 (11)
β (°)	95.074 (6)
V (Å³)	1111.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.984, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6560, 2102, 1522
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.169, 1.01
No. of reflections	2102
No. of parameters	285
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.33

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.8200	1.9100	2.561 (5)	135.00
O4—H4···N1	0.82 (8)	1.83 (8)	2.601 (6)	157 (8)

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

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
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gan, C. S. (2008). Can. J. Chem. 86, 261–263. Web of Science CrossRef CAS Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-[(E)-({3-[(E)-(2-Hy­dr­oxy­benzyl­­idene)amino­meth­yl]-1,4-dioxa­spiro­[4.5]decan-2-yl}meth­yl)imino­meth­yl]phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(E)-({3-[(E)-(2-Hydroxybenzylidene)aminomethyl]-1,4-dioxaspiro[4.5]decan-2-yl}methyl)iminomethyl]phenol