[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-di-yl]bis-[N-(thio-phen-2-yl-methyl-idene)methanamine].

In the title compound, C(17)H(20)N(2)O(2)S(2), the five-membered heterocycle exhibits an envelope conformation and the mol-ecular chirality and configuration are well preserved from l-tartaric acid. The dihedral angle between the two thio-phene rings is 17.0 (2)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯S hydrogen inter-actions, 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 = 348.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.02

3140 reflections

211 parameters

19 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1322 Friedel pairs

Flack parameter: 0.00 (8)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001298/fk2048sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812001298/fk2048Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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	Flack parameter: 0.00 (8)

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

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) ; (ii) .