[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-di­yl]bis­[N-(thio­phen-2-yl­methyl­idene)methanamine]

Jiang, Y.; Bian, J.; Sun, X.

doi:10.1107/S1600536812001298

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o430

doi:10.1107/S1600536812001298

Open

access

[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis[N-(thiophen-2-ylmethylidene)methanamine]

Yan Jiang,^a Jing Bian ^a and Xiaoqiang Sun ^a ^*

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

(Received 8 December 2011; accepted 11 January 2012; online 18 January 2012)

In the title compound, C₁₇H₂₀N₂O₂S₂, the five-membered heterocycle exhibits an envelope conformation and the molecular chirality and configuration are well preserved from L-tartaric acid. The dihedral angle between the two thiophene rings is 17.0 (2)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯S hydrogen interactions, which are effective in the stabilization of the crystal structure.

Related literature

For general background to spiranes, see: Takashi et al. (2011 ); Yong (2001 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₂S₂
M_r = 348.47
Monoclinic, P 2₁
a = 10.475 (2) Å
b = 7.4792 (15) Å
c = 11.533 (2) Å
β = 92.339 (4)°
V = 902.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.942, T_max = 0.956
5249 measured reflections
3140 independent reflections
2575 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.092
S = 1.02
3140 reflections
211 parameters
19 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1322 Friedel pairs
Flack parameter: 0.00 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.93	2.56	3.431 (4)	155
C8—H8⋯S2ⁱ	0.93	2.94	3.793 (3)	153
C12—H12⋯O1ⁱⁱ	0.93	2.68	3.466 (4)	143
Symmetry codes: (i) $[-x+3, y+{\script{1\over 2}}, -z+2]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001298/fk2048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001298/fk2048Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001298/fk2048Isup3.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 (Yong, 2001). The L-(+)-tartaric acid is a well known chiral pool possessing two useful chiral centers which is an important chiral material in synthesis (Takashi et al., 2011). Herein, we synthesized ((4S,5S)-2,2-dimethyl-1,3- dioxolane-4,5-diyl)bis(N-(thiophen-2-ylmethylene)methanamine) based on L-tartaric acid and present the structure of it. The five-membered heterocycle (Fig. 1) adopts envelope conformation, the molecular chirality and configuration are well preserved from L-tartaric acid. The dihedral angle between the two thiofuran rings is 17.0 (2)°. Molecules are linked by intermolecular weak hydrogen interactions (C—H···O and C—H···S) and probabely C—H···π interactions which are effective in the stabilization of the crystal structure. Fig. 2 shows the crystal packing of the title compound along the c axis.

Related literature top

For general background to spiranes, see: Takashi et al. (2011); Yong (2001).

Experimental top

To a solution of 2-thiophenealdehyde (0.9 g, 8.04 mmol) in ethanol (10 ml), ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanamine (0.6 g, 3.75 mmol) dissolved in ethanol (10 ml) was added. The mixture was refluxed for 2 h to complete the reaction and then cooled to room temperature. The compound was recrystallized from ethanol to afford a yellow solid (1 g, 76% yield, m.p. 361.5–363.4 K). Single crystals suitable for X-ray diffraction were also obtained by evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along the c axis. Dashed lines indicate C—H···O and C—H···S interactions.

[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis[N- (thiophen-2-ylmethylidene)methanamine] top

Crystal data top

C₁₇H₂₀N₂O₂S₂	F(000) = 368
M_r = 348.47	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1762 reflections
a = 10.475 (2) Å	θ = 2.6–24.3°
b = 7.4792 (15) Å	µ = 0.31 mm⁻¹
c = 11.533 (2) Å	T = 296 K
β = 92.339 (4)°	Block, colourless
V = 902.8 (3) Å³	0.20 × 0.18 × 0.15 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3140 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
phi and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→12
T_min = 0.942, T_max = 0.956	k = −9→8
5249 measured reflections	l = −13→13

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0442P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3140 reflections	Δρ_max = 0.14 e Å⁻³
211 parameters	Δρ_min = −0.18 e Å⁻³
19 restraints	Absolute structure: Flack (1983), 1322 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Crystal data top

C₁₇H₂₀N₂O₂S₂	V = 902.8 (3) Å³
M_r = 348.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.475 (2) Å	µ = 0.31 mm⁻¹
b = 7.4792 (15) Å	T = 296 K
c = 11.533 (2) Å	0.20 × 0.18 × 0.15 mm
β = 92.339 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3140 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2575 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.956	R_int = 0.043
5249 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.14 e Å⁻³
S = 1.02	Δρ_min = −0.18 e Å⁻³
3140 reflections	Absolute structure: Flack (1983), 1322 Friedel pairs
211 parameters	Absolute structure parameter: 0.00 (8)
19 restraints

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
S1	0.51034 (7)	0.34500 (12)	0.54421 (6)	0.0557 (2)
S2	1.38990 (7)	0.13103 (10)	1.18352 (6)	0.0563 (2)
C1	0.5853 (2)	0.1387 (4)	0.7331 (2)	0.0410 (6)
H1	0.5679	0.0569	0.7911	0.049*
C2	0.4830 (2)	0.1972 (4)	0.6549 (2)	0.0401 (6)
N1	0.6976 (2)	0.1954 (3)	0.72485 (19)	0.0479 (6)
C3	1.4097 (2)	0.2230 (4)	1.0493 (2)	0.0437 (6)
O1	1.10405 (16)	−0.0651 (3)	0.77918 (17)	0.0565 (5)
C4	1.3054 (3)	0.2405 (4)	0.9630 (2)	0.0471 (7)
H4	1.3210	0.3027	0.8953	0.056*
N2	1.1964 (2)	0.1774 (4)	0.97401 (19)	0.0530 (6)
C5	1.0211 (3)	−0.1649 (4)	0.7025 (2)	0.0537 (7)
C6	1.1023 (3)	0.2134 (4)	0.8812 (3)	0.0531 (7)
H6A	1.1456	0.2609	0.8151	0.064*
H6B	1.0440	0.3046	0.9069	0.064*
C7	0.7933 (3)	0.1333 (5)	0.8120 (2)	0.0567 (8)
H7A	0.7628	0.0256	0.8487	0.068*
H7B	0.8061	0.2240	0.8715	0.068*
C8	1.5345 (3)	0.2735 (4)	1.0366 (2)	0.0495 (7)
H8	1.5644	0.3257	0.9698	0.059*
C9	1.6117 (3)	0.2371 (5)	1.1363 (3)	0.0608 (8)
H9	1.6984	0.2638	1.1430	0.073*
C10	0.3523 (3)	0.3486 (6)	0.5036 (3)	0.0653 (8)
H10	0.3180	0.4158	0.4419	0.078*
C11	0.9188 (2)	0.0949 (4)	0.7565 (2)	0.0457 (7)
H11	0.9426	0.1971	0.7088	0.055*
O2	0.90851 (19)	−0.0604 (3)	0.6865 (2)	0.0779 (7)
C12	0.3575 (3)	0.1538 (5)	0.6571 (2)	0.0538 (7)
H12	0.3242	0.0739	0.7097	0.065*
C13	0.2831 (3)	0.2434 (5)	0.5706 (3)	0.0670 (9)
H13	0.1949	0.2306	0.5612	0.080*
C14	1.5472 (3)	0.1603 (5)	1.2200 (3)	0.0615 (9)
H14	1.5845	0.1262	1.2912	0.074*
C15	1.0267 (2)	0.0527 (4)	0.8430 (2)	0.0453 (7)
H15	0.9937	−0.0092	0.9105	0.054*
C16	0.9858 (4)	−0.3401 (5)	0.7552 (4)	0.0851 (11)
H16A	0.9536	−0.3199	0.8308	0.128*
H16B	1.0599	−0.4155	0.7617	0.128*
H16C	0.9212	−0.3972	0.7067	0.128*
C17	1.0853 (3)	−0.1869 (6)	0.5889 (3)	0.0855 (12)
H17A	1.0303	−0.2529	0.5358	0.128*
H17B	1.1642	−0.2504	0.6016	0.128*
H17C	1.1022	−0.0712	0.5568	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0541 (4)	0.0605 (5)	0.0525 (4)	0.0002 (4)	0.0023 (3)	0.0154 (4)
S2	0.0611 (5)	0.0610 (5)	0.0466 (4)	−0.0102 (4)	−0.0018 (3)	0.0023 (4)
C1	0.0447 (15)	0.0404 (15)	0.0378 (13)	0.0071 (13)	0.0013 (11)	−0.0003 (13)
C2	0.0392 (14)	0.0417 (15)	0.0394 (13)	0.0054 (12)	0.0011 (11)	−0.0008 (12)
N1	0.0394 (13)	0.0531 (16)	0.0507 (13)	0.0081 (11)	−0.0034 (10)	0.0050 (11)
C3	0.0493 (16)	0.0386 (15)	0.0428 (14)	−0.0064 (13)	−0.0028 (12)	−0.0072 (12)
O1	0.0404 (10)	0.0560 (13)	0.0717 (12)	0.0093 (9)	−0.0144 (9)	−0.0117 (11)
C4	0.0574 (18)	0.0430 (16)	0.0401 (14)	−0.0056 (14)	−0.0061 (13)	−0.0031 (13)
N2	0.0486 (13)	0.0649 (18)	0.0445 (12)	−0.0056 (12)	−0.0102 (10)	−0.0034 (12)
C5	0.0486 (15)	0.0469 (17)	0.0646 (17)	0.0053 (15)	−0.0102 (13)	−0.0117 (16)
C6	0.0515 (16)	0.0516 (19)	0.0553 (17)	0.0053 (14)	−0.0082 (14)	−0.0019 (15)
C7	0.0461 (16)	0.072 (2)	0.0519 (16)	0.0054 (16)	−0.0050 (13)	0.0108 (17)
C8	0.0515 (18)	0.0472 (17)	0.0497 (16)	−0.0113 (13)	0.0018 (14)	−0.0049 (14)
C9	0.0450 (16)	0.062 (2)	0.075 (2)	−0.0085 (15)	−0.0073 (16)	−0.0150 (18)
C10	0.0618 (19)	0.077 (2)	0.0566 (17)	0.008 (2)	−0.0081 (15)	0.020 (2)
C11	0.0415 (14)	0.0458 (17)	0.0489 (14)	0.0037 (12)	−0.0092 (12)	−0.0010 (12)
O2	0.0607 (13)	0.0720 (16)	0.0975 (16)	0.0196 (12)	−0.0402 (12)	−0.0357 (14)
C12	0.0469 (15)	0.063 (2)	0.0516 (16)	−0.0044 (15)	0.0005 (13)	0.0115 (16)
C13	0.0433 (17)	0.084 (3)	0.072 (2)	0.0022 (17)	−0.0138 (16)	0.015 (2)
C14	0.0631 (19)	0.061 (2)	0.0581 (18)	0.0014 (17)	−0.0218 (15)	0.0003 (17)
C15	0.0390 (14)	0.0486 (16)	0.0476 (15)	0.0041 (13)	−0.0089 (12)	0.0022 (14)
C16	0.086 (2)	0.061 (2)	0.108 (3)	−0.010 (2)	−0.003 (2)	0.004 (2)
C17	0.073 (2)	0.106 (4)	0.077 (2)	−0.012 (2)	0.0019 (19)	−0.017 (2)

Geometric parameters (Å, º) top

S1—C10	1.703 (3)	C7—H7A	0.9700
S1—C2	1.721 (3)	C7—H7B	0.9700
S2—C14	1.699 (3)	C8—C9	1.404 (4)
S2—C3	1.714 (3)	C8—H8	0.9300
C1—N1	1.258 (3)	C9—C14	1.331 (5)
C1—C2	1.440 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C13	1.337 (5)
C2—C12	1.355 (4)	C10—H10	0.9300
N1—C7	1.466 (3)	C11—O2	1.417 (3)
C3—C8	1.375 (4)	C11—C15	1.510 (3)
C3—C4	1.453 (3)	C11—H11	0.9800
O1—C15	1.422 (3)	C12—C13	1.410 (4)
O1—C5	1.425 (3)	C12—H12	0.9300
C4—N2	1.247 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
N2—C6	1.450 (3)	C15—H15	0.9800
C5—O2	1.421 (3)	C16—H16A	0.9600
C5—C16	1.497 (5)	C16—H16B	0.9600
C5—C17	1.505 (4)	C16—H16C	0.9600
C6—C15	1.496 (4)	C17—H17A	0.9600
C6—H6A	0.9700	C17—H17B	0.9600
C6—H6B	0.9700	C17—H17C	0.9600
C7—C11	1.513 (4)

C10—S1—C2	91.42 (15)	C14—C9—H9	123.7
C14—S2—C3	91.17 (15)	C8—C9—H9	123.7
N1—C1—C2	121.6 (3)	C13—C10—S1	112.0 (2)
N1—C1—H1	119.2	C13—C10—H10	124.0
C2—C1—H1	119.2	S1—C10—H10	124.0
C12—C2—C1	127.8 (3)	O2—C11—C15	104.0 (2)
C12—C2—S1	111.0 (2)	O2—C11—C7	110.4 (2)
C1—C2—S1	121.2 (2)	C15—C11—C7	113.6 (2)
C1—N1—C7	117.2 (2)	O2—C11—H11	109.5
C8—C3—C4	126.4 (3)	C15—C11—H11	109.5
C8—C3—S2	110.9 (2)	C7—C11—H11	109.5
C4—C3—S2	122.6 (2)	C11—O2—C5	109.5 (2)
C15—O1—C5	107.45 (19)	C2—C12—C13	112.4 (3)
N2—C4—C3	124.2 (3)	C2—C12—H12	123.8
N2—C4—H4	117.9	C13—C12—H12	123.8
C3—C4—H4	117.9	C10—C13—C12	113.1 (3)
C4—N2—C6	116.9 (2)	C10—C13—H13	123.5
O2—C5—O1	105.9 (2)	C12—C13—H13	123.5
O2—C5—C16	108.4 (3)	C9—C14—S2	113.0 (2)
O1—C5—C16	111.2 (3)	C9—C14—H14	123.5
O2—C5—C17	110.2 (3)	S2—C14—H14	123.5
O1—C5—C17	108.3 (3)	O1—C15—C6	110.1 (2)
C16—C5—C17	112.6 (3)	O1—C15—C11	102.4 (2)
N2—C6—C15	113.8 (2)	C6—C15—C11	113.5 (2)
N2—C6—H6A	108.8	O1—C15—H15	110.2
C15—C6—H6A	108.8	C6—C15—H15	110.2
N2—C6—H6B	108.8	C11—C15—H15	110.2
C15—C6—H6B	108.8	C5—C16—H16A	109.5
H6A—C6—H6B	107.7	C5—C16—H16B	109.5
N1—C7—C11	110.6 (2)	H16A—C16—H16B	109.5
N1—C7—H7A	109.5	C5—C16—H16C	109.5
C11—C7—H7A	109.5	H16A—C16—H16C	109.5
N1—C7—H7B	109.5	H16B—C16—H16C	109.5
C11—C7—H7B	109.5	C5—C17—H17A	109.5
H7A—C7—H7B	108.1	C5—C17—H17B	109.5
C3—C8—C9	112.2 (3)	H17A—C17—H17B	109.5
C3—C8—H8	123.9	C5—C17—H17C	109.5
C9—C8—H8	123.9	H17A—C17—H17C	109.5
C14—C9—C8	112.7 (3)	H17B—C17—H17C	109.5

N1—C1—C2—C12	−176.7 (3)	N1—C7—C11—C15	172.7 (3)
N1—C1—C2—S1	1.3 (4)	C15—C11—O2—C5	−16.5 (3)
C10—S1—C2—C12	0.7 (3)	C7—C11—O2—C5	−138.8 (3)
C10—S1—C2—C1	−177.6 (2)	O1—C5—O2—C11	−3.2 (3)
C2—C1—N1—C7	177.3 (2)	C16—C5—O2—C11	116.2 (3)
C14—S2—C3—C8	−0.2 (2)	C17—C5—O2—C11	−120.1 (3)
C14—S2—C3—C4	179.2 (3)	C1—C2—C12—C13	176.8 (3)
C8—C3—C4—N2	172.8 (3)	S1—C2—C12—C13	−1.3 (4)
S2—C3—C4—N2	−6.5 (4)	S1—C10—C13—C12	−0.8 (4)
C3—C4—N2—C6	177.7 (3)	C2—C12—C13—C10	1.4 (5)
C15—O1—C5—O2	23.2 (3)	C8—C9—C14—S2	−0.9 (4)
C15—O1—C5—C16	−94.4 (3)	C3—S2—C14—C9	0.6 (3)
C15—O1—C5—C17	141.4 (3)	C5—O1—C15—C6	−153.6 (2)
C4—N2—C6—C15	134.1 (3)	C5—O1—C15—C11	−32.6 (3)
C1—N1—C7—C11	140.1 (3)	N2—C6—C15—O1	−72.7 (3)
C4—C3—C8—C9	−179.6 (3)	N2—C6—C15—C11	173.2 (2)
S2—C3—C8—C9	−0.2 (3)	O2—C11—C15—O1	29.7 (3)
C3—C8—C9—C14	0.7 (4)	C7—C11—C15—O1	149.8 (3)
C2—S1—C10—C13	0.1 (3)	O2—C11—C15—C6	148.3 (2)
N1—C7—C11—O2	−70.8 (3)	C7—C11—C15—C6	−91.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.56	3.431 (4)	155
C8—H8···S2ⁱ	0.93	2.94	3.793 (3)	153
C12—H12···O1ⁱⁱ	0.93	2.68	3.466 (4)	143

Symmetry codes: (i) −x+3, y+1/2, −z+2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₂S₂
M_r	348.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	10.475 (2), 7.4792 (15), 11.533 (2)
β (°)	92.339 (4)
V (Å³)	902.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.942, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	5249, 3140, 2575
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.092, 1.02
No. of reflections	3140
No. of parameters	211
No. of restraints	19
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18
Absolute structure	Flack (1983), 1322 Friedel pairs
Absolute structure parameter	0.00 (8)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.56	3.431 (4)	155.2
C8—H8···S2ⁱ	0.93	2.94	3.793 (3)	153.3
C12—H12···O1ⁱⁱ	0.93	2.68	3.466 (4)	142.6

Symmetry codes: (i) −x+3, y+1/2, −z+2; (ii) x−1, y, z.

Acknowledgements

We gratefully acknowledge financial support from the Natural Science Foundation of China (No. 20872051).

References

Bruker (2000). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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
Takashi, T., Yuki, Y., Tohru, T. & Tracy, K. S. (2011). J. Org. Chem. 76, 4669–4674. Web of Science PubMed Google Scholar
Yong, H. K. (2001). Acc. Chem. Res. 34, 955–962. Web of Science PubMed 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 68| Part 2| February 2012| Page o430

doi:10.1107/S1600536812001298

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

[(4S,5S)-2,2-Di­methyl-1,3-dioxolane-4,5-di­yl]bis­­[N-(thio­phen-2-yl­methyl­­idene)methanamine]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis[N-(thiophen-2-ylmethylidene)methanamine]