2-{(1S*,2S*)-2-[(E)-(2,4-Dihy­droxy­benzyl­idene)amino]­cyclo­hex­yl}isoindoline-1,3-dione

Liu, Z.-J.; Fu, X.-K.; Hu, Z.-K.; Wu, X.-J.; Wu, L.

doi:10.1107/S1600536811019787

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1562

doi:10.1107/S1600536811019787

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2-{(1S,2S)-2-[(E)-(2,4-Dihydroxybenzylidene)amino]cyclohexyl}isoindoline-1,3-dione

Zhi-Jian Liu,^a Xiang-Kai Fu,^a ^* Zhong-Kai Hu,^a Xiao-Ju Wu ^a and Liu Wu ^a

^aCollege of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry, Southwest University, The Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: fxk@swu.edu.cn

(Received 17 May 2011; accepted 25 May 2011; online 4 June 2011)

In the title molecule, C₂₁H₂₀N₂O₄, the dihedral angle between the phenol ring and the isoindole-1,3-dione mean plane is 69.79 (6)°. The cyclohexane ring adopts a chair conformation. Weak intermolecular O—H⋯O and O—H⋯N interactions feature as part of the crystal packing.

Related literature

For details of the synthesis, see: Berkessel et al. (2006 ); Ren & Fu (2009 ). For background to the synthesis of salen-type Schiff base ligands, see: Campbell & Nguyen (2001 ).

Experimental

Crystal data

C₂₁H₂₀N₂O₄
M_r = 364.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.0247 (3) Å
b = 11.7748 (4) Å
c = 17.8585 (6) Å
V = 1897.72 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.982
34622 measured reflections
4727 independent reflections
4317 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.132
S = 1.10
4727 reflections
251 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.93 (1)	1.69 (1)	2.5656 (16)	157 (2)
O4—H4B⋯O3ⁱ	0.90 (2)	1.66 (2)	2.5478 (15)	170 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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: 10.1107/S1600536811019787/ff2012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019787/ff2012Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019787/ff2012Isup3.cml

checkCIF report

Comment top

Salen-type Schiff base ligands incorporating two different benzylidene moieties and a diamine backbone were synthesized in high yield under mild conditions via a stepwise approach. In the synthesis of salen-type Schiff base ligands (Campbell et al., 2001), the compound (I) was a significant intermediate product. Here we report its crystal structure.

Related literature top

For details of the synthesis, see: Berkessel et al. (2006); Ren & Fu (2009). For background to the synthesis of salen-type Schiff base ligands, see: Campbell & Nguyen (2001).

Experimental top

Compound (I) was synthesized according to the procedure of Berkessel et al. (2006); Ren et al. (2009). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of ethanol and acetonitrile (1:1) by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. Molecular structure showing 30% probability displacement ellipsoids.

2-{(1S*,2S*)-2-[(E)-(2,4- Dihydroxybenzylidene)amino]cyclohexyl}isoindoline-1,3-dione top

Crystal data top

C₂₁H₂₀N₂O₄	D_x = 1.275 Mg m⁻³
M_r = 364.39	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 34622 reflections
a = 9.0247 (3) Å	θ = 2.1–28.3°
b = 11.7748 (4) Å	µ = 0.09 mm⁻¹
c = 17.8585 (6) Å	T = 296 K
V = 1897.72 (11) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.20 mm
F(000) = 768

Data collection top

Bruker APEX CCD area-detector diffractometer	4727 independent reflections
Radiation source: fine-focus sealed tube	4317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.982, T_max = 0.982	k = −15→15
34622 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
4727 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₁H₂₀N₂O₄	V = 1897.72 (11) Å³
M_r = 364.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.0247 (3) Å	µ = 0.09 mm⁻¹
b = 11.7748 (4) Å	T = 296 K
c = 17.8585 (6) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	4727 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4317 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.982	R_int = 0.023
34622 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.26 e Å⁻³
4727 reflections	Δρ_min = −0.32 e Å⁻³
251 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
C1	0.30161 (15)	0.36416 (11)	0.06573 (7)	0.0377 (3)
C2	0.42917 (15)	0.34393 (11)	0.02192 (7)	0.0388 (3)
H2B	0.4445	0.2721	0.0017	0.047*
C3	0.53102 (15)	0.42835 (11)	0.00866 (7)	0.0405 (3)
C4	0.5076 (2)	0.53951 (12)	0.03634 (11)	0.0576 (4)
H4A	0.5759	0.5967	0.0262	0.069*
C5	0.3856 (2)	0.56221 (12)	0.07755 (10)	0.0551 (4)
H5A	0.3702	0.6358	0.0948	0.066*
C6	0.28074 (16)	0.47702 (11)	0.09522 (7)	0.0400 (3)
C7	0.15624 (16)	0.50289 (12)	0.13977 (7)	0.0442 (3)
H7A	0.1438	0.5774	0.1559	0.053*
C8	−0.07381 (16)	0.45130 (14)	0.20425 (7)	0.0452 (3)
H8A	−0.0812	0.5330	0.2141	0.054*
C9	−0.21031 (18)	0.4117 (2)	0.16090 (8)	0.0604 (4)
H9A	−0.2190	0.4554	0.1151	0.072*
H9B	−0.1986	0.3324	0.1474	0.072*
C10	−0.3512 (2)	0.4259 (3)	0.20717 (11)	0.0762 (6)
H10A	−0.4352	0.3973	0.1790	0.091*
H10B	−0.3678	0.5060	0.2169	0.091*
C11	−0.3396 (2)	0.3625 (3)	0.28091 (10)	0.0809 (7)
H11A	−0.4287	0.3751	0.3102	0.097*
H11B	−0.3311	0.2817	0.2713	0.097*
C12	−0.2046 (2)	0.4032 (2)	0.32491 (9)	0.0683 (5)
H12A	−0.1969	0.3608	0.3713	0.082*
H12B	−0.2160	0.4829	0.3372	0.082*
C13	−0.06454 (17)	0.38642 (13)	0.27883 (7)	0.0458 (3)
H13A	−0.0588	0.3054	0.2665	0.055*
C14	0.1428 (2)	0.33206 (13)	0.36431 (9)	0.0524 (4)
C15	0.27356 (18)	0.38879 (13)	0.39836 (8)	0.0480 (3)
C16	0.3843 (2)	0.34711 (16)	0.44396 (10)	0.0667 (5)
H16A	0.3845	0.2716	0.4592	0.080*
C17	0.4951 (2)	0.4208 (2)	0.46639 (11)	0.0683 (5)
H17A	0.5710	0.3945	0.4971	0.082*
C18	0.4943 (2)	0.53120 (17)	0.44398 (10)	0.0631 (5)
H18A	0.5714	0.5787	0.4585	0.076*
C19	0.38096 (18)	0.57462 (14)	0.39993 (10)	0.0549 (4)
H19A	0.3792	0.6507	0.3861	0.066*
C20	0.27078 (16)	0.50062 (12)	0.37739 (7)	0.0432 (3)
C21	0.13765 (16)	0.52076 (11)	0.33052 (7)	0.0420 (3)
N1	0.06951 (15)	0.41440 (10)	0.32197 (6)	0.0446 (3)
N2	0.05849 (14)	0.42829 (11)	0.15940 (6)	0.0445 (3)
O1	0.1041 (2)	0.23425 (11)	0.36929 (9)	0.0804 (5)
O2	0.09328 (16)	0.60904 (9)	0.30445 (7)	0.0612 (3)
O3	0.20554 (13)	0.28623 (9)	0.07975 (7)	0.0560 (3)
H3A	0.141 (2)	0.3207 (16)	0.1129 (9)	0.065*
O4	0.65643 (13)	0.41288 (9)	−0.02971 (7)	0.0526 (3)
H4B	0.665 (3)	0.340 (2)	−0.0447 (12)	0.070 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0332 (6)	0.0376 (6)	0.0423 (5)	−0.0025 (5)	−0.0030 (5)	−0.0034 (4)
C2	0.0352 (6)	0.0353 (5)	0.0459 (5)	−0.0004 (5)	−0.0008 (5)	−0.0045 (5)
C3	0.0371 (6)	0.0386 (6)	0.0459 (6)	0.0001 (5)	0.0037 (5)	−0.0001 (5)
C4	0.0567 (9)	0.0350 (6)	0.0812 (10)	−0.0097 (6)	0.0230 (8)	−0.0054 (6)
C5	0.0574 (9)	0.0341 (6)	0.0737 (9)	−0.0044 (6)	0.0188 (8)	−0.0091 (6)
C6	0.0361 (6)	0.0399 (6)	0.0439 (5)	−0.0015 (5)	0.0010 (5)	−0.0044 (5)
C7	0.0423 (7)	0.0450 (6)	0.0452 (6)	0.0012 (6)	0.0027 (5)	−0.0045 (5)
C8	0.0337 (6)	0.0610 (8)	0.0408 (5)	−0.0011 (6)	0.0023 (5)	−0.0061 (5)
C9	0.0374 (7)	0.0999 (13)	0.0439 (6)	−0.0054 (9)	−0.0031 (6)	−0.0076 (7)
C10	0.0341 (8)	0.130 (2)	0.0648 (9)	−0.0055 (11)	−0.0019 (7)	−0.0189 (11)
C11	0.0448 (9)	0.141 (2)	0.0570 (9)	−0.0316 (12)	0.0100 (7)	−0.0177 (10)
C12	0.0469 (9)	0.1134 (16)	0.0445 (7)	−0.0239 (10)	0.0069 (7)	−0.0135 (8)
C13	0.0407 (7)	0.0544 (7)	0.0423 (6)	−0.0122 (6)	−0.0009 (5)	−0.0059 (5)
C14	0.0586 (9)	0.0461 (7)	0.0524 (7)	−0.0066 (7)	−0.0056 (7)	0.0016 (6)
C15	0.0469 (8)	0.0470 (7)	0.0502 (6)	0.0010 (6)	−0.0045 (6)	−0.0030 (5)
C16	0.0713 (12)	0.0577 (9)	0.0712 (10)	0.0147 (9)	−0.0154 (9)	0.0034 (8)
C17	0.0510 (9)	0.0877 (13)	0.0661 (9)	0.0242 (9)	−0.0171 (8)	−0.0182 (9)
C18	0.0387 (8)	0.0766 (11)	0.0741 (10)	0.0040 (8)	−0.0097 (7)	−0.0236 (9)
C19	0.0422 (8)	0.0529 (8)	0.0695 (9)	−0.0048 (7)	−0.0075 (7)	−0.0107 (7)
C20	0.0391 (7)	0.0449 (6)	0.0456 (6)	0.0002 (6)	−0.0024 (5)	−0.0063 (5)
C21	0.0405 (7)	0.0408 (6)	0.0445 (6)	−0.0048 (5)	−0.0035 (5)	−0.0025 (5)
N1	0.0430 (6)	0.0445 (6)	0.0462 (5)	−0.0079 (5)	−0.0059 (5)	−0.0017 (4)
N2	0.0368 (6)	0.0543 (6)	0.0425 (5)	−0.0017 (5)	0.0042 (4)	−0.0061 (4)
O1	0.1011 (12)	0.0451 (6)	0.0951 (9)	−0.0188 (7)	−0.0246 (9)	0.0109 (6)
O2	0.0689 (8)	0.0429 (5)	0.0719 (6)	−0.0015 (5)	−0.0229 (6)	0.0039 (5)
O3	0.0460 (6)	0.0466 (5)	0.0756 (7)	−0.0154 (5)	0.0170 (5)	−0.0165 (5)
O4	0.0426 (6)	0.0449 (5)	0.0703 (6)	−0.0043 (4)	0.0187 (5)	−0.0051 (5)

Geometric parameters (Å, º) top

C1—O3	1.2869 (16)	C11—H11A	0.9700
C1—C2	1.4122 (18)	C11—H11B	0.9700
C1—C6	1.4418 (17)	C12—C13	1.521 (2)
C2—C3	1.3744 (19)	C12—H12A	0.9700
C2—H2B	0.9300	C12—H12B	0.9700
C3—O4	1.3355 (16)	C13—N1	1.4716 (17)
C3—C4	1.4150 (19)	C13—H13A	0.9800
C4—C5	1.351 (2)	C14—O1	1.207 (2)
C4—H4A	0.9300	C14—N1	1.396 (2)
C5—C6	1.415 (2)	C14—C15	1.486 (2)
C5—H5A	0.9300	C15—C20	1.369 (2)
C6—C7	1.4101 (19)	C15—C16	1.380 (2)
C7—N2	1.2933 (19)	C16—C17	1.383 (3)
C7—H7A	0.9300	C16—H16A	0.9300
C8—N2	1.4630 (17)	C17—C18	1.361 (3)
C8—C9	1.528 (2)	C17—H17A	0.9300
C8—C13	1.5377 (19)	C18—C19	1.388 (2)
C8—H8A	0.9800	C18—H18A	0.9300
C9—C10	1.525 (2)	C19—C20	1.382 (2)
C9—H9A	0.9700	C19—H19A	0.9300
C9—H9B	0.9700	C20—C21	1.4833 (19)
C10—C11	1.518 (3)	C21—O2	1.2073 (18)
C10—H10A	0.9700	C21—N1	1.4036 (18)
C10—H10B	0.9700	O3—H3A	0.927 (9)
C11—C12	1.527 (2)	O4—H4B	0.90 (2)

O3—C1—C2	122.46 (11)	H11A—C11—H11B	108.1
O3—C1—C6	119.88 (12)	C11—C12—C13	110.13 (13)
C2—C1—C6	117.66 (11)	C11—C12—H12A	109.6
C3—C2—C1	121.25 (11)	C13—C12—H12A	109.6
C3—C2—H2B	119.4	C11—C12—H12B	109.6
C1—C2—H2B	119.4	C13—C12—H12B	109.6
O4—C3—C2	123.82 (12)	H12A—C12—H12B	108.1
O4—C3—C4	115.58 (12)	N1—C13—C12	111.77 (10)
C2—C3—C4	120.60 (12)	N1—C13—C8	112.77 (11)
C5—C4—C3	119.66 (13)	C12—C13—C8	111.04 (14)
C5—C4—H4A	120.2	N1—C13—H13A	107.0
C3—C4—H4A	120.2	C12—C13—H13A	107.0
C4—C5—C6	121.77 (13)	C8—C13—H13A	107.0
C4—C5—H5A	119.1	O1—C14—N1	124.41 (16)
C6—C5—H5A	119.1	O1—C14—C15	128.97 (17)
C7—C6—C5	120.39 (12)	N1—C14—C15	106.61 (12)
C7—C6—C1	120.61 (12)	C20—C15—C16	121.12 (15)
C5—C6—C1	118.98 (12)	C20—C15—C14	107.81 (13)
N2—C7—C6	123.35 (13)	C16—C15—C14	131.07 (15)
N2—C7—H7A	118.3	C17—C16—C15	118.15 (17)
C6—C7—H7A	118.3	C17—C16—H16A	120.9
N2—C8—C9	108.92 (11)	C15—C16—H16A	120.9
N2—C8—C13	109.74 (12)	C18—C17—C16	120.68 (17)
C9—C8—C13	109.34 (13)	C18—C17—H17A	119.7
N2—C8—H8A	109.6	C16—C17—H17A	119.7
C9—C8—H8A	109.6	C17—C18—C19	121.53 (17)
C13—C8—H8A	109.6	C17—C18—H18A	119.2
C10—C9—C8	111.36 (12)	C19—C18—H18A	119.2
C10—C9—H9A	109.4	C20—C19—C18	117.58 (16)
C8—C9—H9A	109.4	C20—C19—H19A	121.2
C10—C9—H9B	109.4	C18—C19—H19A	121.2
C8—C9—H9B	109.4	C15—C20—C19	120.90 (14)
H9A—C9—H9B	108.0	C15—C20—C21	108.84 (13)
C9—C10—C11	111.02 (17)	C19—C20—C21	130.27 (14)
C9—C10—H10A	109.4	O2—C21—N1	125.52 (13)
C11—C10—H10A	109.4	O2—C21—C20	128.60 (13)
C9—C10—H10B	109.4	N1—C21—C20	105.88 (11)
C11—C10—H10B	109.4	C14—N1—C21	110.67 (11)
H10A—C10—H10B	108.0	C14—N1—C13	121.18 (12)
C12—C11—C10	110.31 (18)	C21—N1—C13	128.09 (12)
C12—C11—H11A	109.6	C7—N2—C8	125.40 (13)
C10—C11—H11A	109.6	C1—O3—H3A	103.8 (13)
C12—C11—H11B	109.6	C3—O4—H4B	110.7 (15)
C10—C11—H11B	109.6

O3—C1—C2—C3	−179.12 (13)	C20—C15—C16—C17	−1.7 (3)
C6—C1—C2—C3	0.89 (18)	C14—C15—C16—C17	178.88 (18)
C1—C2—C3—O4	177.16 (12)	C15—C16—C17—C18	0.0 (3)
C1—C2—C3—C4	−2.5 (2)	C16—C17—C18—C19	1.9 (3)
O4—C3—C4—C5	−178.20 (16)	C17—C18—C19—C20	−2.1 (3)
C2—C3—C4—C5	1.5 (3)	C16—C15—C20—C19	1.5 (2)
C3—C4—C5—C6	1.1 (3)	C14—C15—C20—C19	−178.98 (14)
C4—C5—C6—C7	178.57 (16)	C16—C15—C20—C21	−178.48 (14)
C4—C5—C6—C1	−2.7 (3)	C14—C15—C20—C21	1.04 (17)
O3—C1—C6—C7	0.4 (2)	C18—C19—C20—C15	0.4 (2)
C2—C1—C6—C7	−179.62 (11)	C18—C19—C20—C21	−179.62 (14)
O3—C1—C6—C5	−178.38 (14)	C15—C20—C21—O2	176.27 (16)
C2—C1—C6—C5	1.6 (2)	C19—C20—C21—O2	−3.7 (3)
C5—C6—C7—N2	−178.23 (14)	C15—C20—C21—N1	−3.42 (16)
C1—C6—C7—N2	3.0 (2)	C19—C20—C21—N1	176.60 (15)
N2—C8—C9—C10	176.03 (17)	O1—C14—N1—C21	177.16 (18)
C13—C8—C9—C10	56.1 (2)	C15—C14—N1—C21	−4.00 (17)
C8—C9—C10—C11	−56.8 (2)	O1—C14—N1—C13	−0.2 (3)
C9—C10—C11—C12	57.0 (3)	C15—C14—N1—C13	178.65 (12)
C10—C11—C12—C13	−57.9 (3)	O2—C21—N1—C14	−175.12 (16)
C11—C12—C13—N1	−174.55 (17)	C20—C21—N1—C14	4.58 (16)
C11—C12—C13—C8	58.6 (2)	O2—C21—N1—C13	2.0 (2)
N2—C8—C13—N1	56.93 (16)	C20—C21—N1—C13	−178.30 (12)
C9—C8—C13—N1	176.34 (13)	C12—C13—N1—C14	89.91 (19)
N2—C8—C13—C12	−176.74 (13)	C8—C13—N1—C14	−144.14 (14)
C9—C8—C13—C12	−57.33 (18)	C12—C13—N1—C21	−86.94 (19)
O1—C14—C15—C20	−179.50 (19)	C8—C13—N1—C21	39.01 (19)
N1—C14—C15—C20	1.73 (18)	C6—C7—N2—C8	−178.75 (12)
O1—C14—C15—C16	0.0 (3)	C9—C8—N2—C7	124.08 (16)
N1—C14—C15—C16	−178.81 (17)	C13—C8—N2—C7	−116.25 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.93 (1)	1.69 (1)	2.5656 (16)	157 (2)
O4—H4B···O3ⁱ	0.90 (2)	1.66 (2)	2.5478 (15)	170 (2)

Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₂O₄
M_r	364.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.0247 (3), 11.7748 (4), 17.8585 (6)
V (Å³)	1897.72 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	34622, 4727, 4317
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.132, 1.10
No. of reflections	4727
No. of parameters	251
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), 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—H3A···N2	0.927 (9)	1.686 (12)	2.5656 (16)	157.2 (19)
O4—H4B···O3ⁱ	0.90 (2)	1.66 (2)	2.5478 (15)	170 (2)

Symmetry code: (i) x+1/2, −y+1/2, −z.

Acknowledgements

The authors are grateful to Southwest University of China for financial support.

References

Berkessel, A., Mukherjee, S., Müller, T. N., Cleemann, F., Roland, K., Brandenburg, Neudörfl, J. & Lex, J. (2006). Org. Biomol. Chem. 4, 4319-4330. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Campbell, J. E. & Nguyen, S. T. (2001). Tetrahedron Lett. 42, 1221–1225. CrossRef CAS Google Scholar
Ren, W. & Fu, X. (2009). J. Mol. Catal. A, 312, 40–47. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1562

doi:10.1107/S1600536811019787

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

2-{(1S*,2S*)-2-[(E)-(2,4-Dihy­dr­oxy­benzyl­­idene)amino]­cyclo­hex­yl}isoindoline-1,3-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{(1S,2S)-2-[(E)-(2,4-Dihydroxybenzylidene)amino]cyclohexyl}isoindoline-1,3-dione