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organic compounds
[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis[N-(thiophen-2-ylmethylidene)methanamine]
aKey Laboratory of Fine Chemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
*Correspondence e-mail: chemsxq@yahoo.com.cn
In the title compound, C17H20N2O2S2, the five-membered heterocycle exhibits an and the molecular 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.
Experimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell 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
10.1107/S1600536812001298/fk2048sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812001298/fk2048Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812001298/fk2048Isup3.cml
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.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.98 Å, and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). As the
was not unambiguous the data were refined using TWIN and BASF.Data collection: SMART (Bruker, 2000); cell
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).C17H20N2O2S2 | F(000) = 368 |
Mr = 348.47 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 3140 independent reflections |
Radiation source: fine-focus sealed tube | 2575 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
phi and ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −8→12 |
Tmin = 0.942, Tmax = 0.956 | k = −9→8 |
5249 measured reflections | l = −13→13 |
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(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3140 reflections | Δρmax = 0.14 e Å−3 |
211 parameters | Δρmin = −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) |
C17H20N2O2S2 | V = 902.8 (3) Å3 |
Mr = 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)° |
Bruker SMART CCD area-detector diffractometer | 3140 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2575 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.956 | Rint = 0.043 |
5249 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.092 | Δρmax = 0.14 e Å−3 |
S = 1.02 | Δρmin = −0.18 e Å−3 |
3140 reflections | Absolute structure: Flack (1983), 1322 Friedel pairs |
211 parameters | Absolute structure parameter: 0.00 (8) |
19 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.942, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5249, 3140, 2575 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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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.