[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetra­methyl­tetra­hydro-3aH-bis­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-3a-yl]methyl (R)-N-(1-phenyl­eth­yl)sulfamate

Xie, M.; Shen, S.-S.; Chen, B.-F.; Sha, Y.

doi:10.1107/S1600536812016704

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1581

doi:10.1107/S1600536812016704

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[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-3a-yl]methyl (R)-N-(1-phenylethyl)sulfamate

Meng Xie,^a Si-Si Shen,^a Bao-Feng Chen ^a and Yu Sha ^a ^*

^aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Mail Box 40, 103 Wenhua Road, Shenhe District, Shenyang 110016, People's Republic of China
^*Correspondence e-mail: shayu@syphu.edu.cn

(Received 3 April 2012; accepted 17 April 2012; online 28 April 2012)

In the title compound, C₂₀H₂₉NO₈S, the two five-membered rings adopt envelope conformations (with an O atom at the flap in each case), while the six-membered pyran ring displays a twist-boat conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into a supramolecular chain running along the a axis.

Related literature

For general background to the drug topiramate [systematic name: 2,3:4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate] and its potential bioactivity, see: Maryanoff (2009 ); Maryanoff et al. (2008 ). For related structures, see: Maryanoff et al. (1998 ); Winum et al. (2006 ).

Experimental

Crystal data

C₂₀H₂₉NO₈S
M_r = 443.50
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.5733 (9) Å
b = 15.0134 (14) Å
c = 15.9462 (15) Å
V = 2291.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.28 × 0.20 × 0.15 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.950, T_max = 0.973
13609 measured reflections
4041 independent reflections
3348 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.100
S = 1.04
4041 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1736 Friedel pairs
Flack parameter: −0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.93	2.06	2.959 (3)	163
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536812016704/xu5509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016704/xu5509Isup2.hkl

checkCIF report

Comment top

The marketed drug Topiramate is a moderate inhibitor of carbonic anhydrase-II(CA—II), which is marketed worldwide for the treatmen of epilepsy and the prophylaxis of migraine headache(Maryanoff et al., 2008). Topiramate easily qualifies as a "billion-dollar molecule". Given the disabling effects of epileptic seizures and the misery associated with recurrent migraine attacks, this drug has helped millions of patients in need across the globe (Maryanoff, 2009). Topiramate is a sulfa-derivative monosaccharide, it contains a sulfamide group, but a sulfamate group is much more effective than the sulfamide group for inhibiting human CA—II (Maryanoff et al., 1998; Winum et al., 2006).

As the derivative of Topiramate that contains a sulfamate group are of great pharmaceutical importance, we have undertaken the crystal structure determination of the title compound. C₂₀H₂₉N₂O₈S, by X-ray diffraction in the crystal packing of (I),[Fig. 2] The bond lengths and angles are within normal ranges. The six-membered ring O4—C10—C11—C12—C13—C14 (substituted pyranoid) is far from planar, and its shape approximates to a twist-boat conformation. In this description applied to this title compound (Fig. 1), atoms C10, C11, C13 and C14 from the bottom of the boat (deviation from the mean C10/C11/C13/C14 plane = 0.176 (4) Å), O4 the prow, and C12 the stern [deviations from the C10/C11/C13/C14 mean plane = 0.557, 0.387 Å, respectively]. The two five-membered rings C10—O6—C15—O5—C11 and C12—O7—C18—O8—C13 (substituted 1,3-dioxolane rings) are non-planar and adopt nearly envelope conformation (deviation from the mean C10/O6/C15/ C11 plane = 0.007 (4) Å, C12/ C18/O8/C13 plane= 0.038 (4) Å). The O5 atom is located above the plane [deviations from the C10/N2/C13/C12 mean plane = 0.473 Å], while the O7 atom is located above the plane [deviations from the C12/ C13/ O8/C18 mean plane = 0.363 Å], Atom C7 of the title molecule is chiral: R configuration was assigned to this atom based on the known chirality of the equivalent atom in the starting material, otherwise, the C10, C11, C12, C13 of the title molecule is chiral: S, S, R, R, respectively. The suIfonyl O atom is engaged in H-bonding with the N—H of the adjacent molecular.

Related literature top

For general background to the drug topiramate [systematic name: 2,3:4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate] and its potential bioactivity, see: Maryanoff (2009); Maryanoff et al. (2008). For related structures, see: Maryanoff et al. (1998); Winum et al. (2006).

Experimental top

((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo [4,5 - b:4',5'-d]pyran-3a-yl)methyl sulfochloridate(7.16 g, 20 mmol) was placed in a round-bottomed flask, and dissolved in acetone(100 ml). Triethylamine(100 mmol)was added and then the (s)-benzenemethanamin (2.57 ml, 20 mmol) and the solution was heated to reflux for 2 h. The mixture was filtered and the filtrate was concentrated under vacuum. The pure product was obtained through silica gel chromatography(eluant petroleum ether:ethyl acetate, 2:1). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in n-hexane:ethyl acetate,6:1 at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 structure of the title compound(I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing of (I), the molecular packing viewed along the b axis, H atoms not involved in hydrogen bonding have been omitted.

[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro- 3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl (R)-N-(1-phenylethyl)sulfamate top

Crystal data top

C₂₀H₂₉NO₈S	D_x = 1.285 Mg m⁻³
M_r = 443.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3967 reflections
a = 9.5733 (9) Å	θ = 2.5–20.8°
b = 15.0134 (14) Å	µ = 0.19 mm⁻¹
c = 15.9462 (15) Å	T = 293 K
V = 2291.9 (4) Å³	Block, colourless
Z = 4	0.28 × 0.20 × 0.15 mm
F(000) = 944

Data collection top

Bruker APEX CCD area-detector diffractometer	4041 independent reflections
Radiation source: fine-focus sealed tube	3348 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.950, T_max = 0.973	k = −17→16
13609 measured reflections	l = −18→18

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0565P)² + 0.0232P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4041 reflections	Δρ_max = 0.14 e Å⁻³
276 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1736 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (8)

Crystal data top

C₂₀H₂₉NO₈S	V = 2291.9 (4) Å³
M_r = 443.50	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.5733 (9) Å	µ = 0.19 mm⁻¹
b = 15.0134 (14) Å	T = 293 K
c = 15.9462 (15) Å	0.28 × 0.20 × 0.15 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	4041 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3348 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.973	R_int = 0.029
13609 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.14 e Å⁻³
S = 1.04	Δρ_min = −0.19 e Å⁻³
4041 reflections	Absolute structure: Flack (1983), 1736 Friedel pairs
276 parameters	Absolute structure parameter: −0.02 (8)
0 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	0.19640 (7)	0.77181 (4)	0.55630 (4)	0.05958 (19)
O1	0.15464 (15)	0.71781 (12)	0.63697 (9)	0.0589 (4)
O2	0.1225 (3)	0.85374 (12)	0.55749 (13)	0.0841 (6)
O3	0.34363 (19)	0.76955 (16)	0.55879 (13)	0.0908 (7)
O4	−0.12573 (18)	0.71591 (11)	0.78266 (10)	0.0623 (5)
O5	0.1236 (2)	0.59605 (12)	0.84887 (12)	0.0785 (6)
O6	0.11065 (19)	0.73889 (11)	0.80456 (10)	0.0623 (5)
O7	−0.15017 (18)	0.53273 (13)	0.70728 (12)	0.0706 (5)
O8	−0.3187 (2)	0.55560 (17)	0.80406 (14)	0.0970 (7)
N1	0.1465 (2)	0.71749 (13)	0.47609 (12)	0.0551 (5)
H1A	0.0538	0.7337	0.4685	0.066*
C1	0.1733 (3)	0.55498 (16)	0.50384 (15)	0.0590 (6)
C2	0.0399 (3)	0.5210 (2)	0.5013 (2)	0.0891 (10)
H2	−0.0258	0.5453	0.4650	0.107*
C3	0.0038 (5)	0.4506 (3)	0.5529 (3)	0.1323 (19)
H3	−0.0864	0.4278	0.5510	0.159*
C4	0.0982 (9)	0.4147 (3)	0.6059 (3)	0.155 (3)
H4	0.0730	0.3675	0.6405	0.186*
C5	0.2294 (8)	0.4476 (3)	0.6085 (3)	0.140 (2)
H5	0.2944	0.4231	0.6452	0.168*
C6	0.2678 (4)	0.5177 (2)	0.5567 (2)	0.0941 (11)
H6	0.3589	0.5392	0.5582	0.113*
C7	0.2137 (2)	0.63303 (15)	0.44935 (14)	0.0525 (5)
H7	0.3150	0.6409	0.4541	0.063*
C8	0.1798 (3)	0.6189 (2)	0.35758 (16)	0.0782 (8)
H8A	0.0805	0.6136	0.3508	0.117*
H8B	0.2242	0.5654	0.3382	0.117*
H8C	0.2131	0.6687	0.3256	0.117*
C9	0.0129 (2)	0.72335 (19)	0.66670 (14)	0.0575 (6)
H9A	−0.0473	0.6859	0.6328	0.069*
H9B	−0.0204	0.7842	0.6629	0.069*
C10	0.0103 (3)	0.69241 (16)	0.75731 (14)	0.0512 (6)
C11	0.0462 (3)	0.59463 (16)	0.77320 (16)	0.0594 (6)
H11	0.1045	0.5717	0.7275	0.071*
C12	−0.0800 (3)	0.53558 (18)	0.78492 (18)	0.0679 (7)
H12	−0.0520	0.4757	0.8026	0.082*
C13	−0.1909 (3)	0.57379 (19)	0.84437 (17)	0.0749 (8)
H13	−0.1873	0.5424	0.8982	0.090*
C14	−0.1693 (3)	0.67232 (19)	0.85826 (17)	0.0769 (9)
H14A	−0.2558	0.6988	0.8778	0.092*
H14B	−0.0990	0.6811	0.9013	0.092*
C15	0.2006 (4)	0.67763 (19)	0.84864 (18)	0.0754 (8)
C16	0.3370 (3)	0.6682 (2)	0.8038 (3)	0.1010 (12)
H16A	0.3960	0.6276	0.8339	0.151*
H16B	0.3818	0.7253	0.8003	0.151*
H16C	0.3208	0.6457	0.7483	0.151*
C17	0.2157 (5)	0.7101 (3)	0.9384 (2)	0.1217 (15)
H17A	0.1248	0.7176	0.9628	0.183*
H17B	0.2642	0.7661	0.9388	0.183*
H17C	0.2677	0.6672	0.9703	0.183*
C18	−0.2960 (3)	0.5233 (2)	0.72210 (19)	0.0735 (8)
C19	−0.3362 (4)	0.4256 (3)	0.7196 (3)	0.1220 (14)
H19A	−0.2824	0.3934	0.7603	0.183*
H19B	−0.3178	0.4022	0.6647	0.183*
H19C	−0.4338	0.4196	0.7321	0.183*
C20	−0.3716 (4)	0.5806 (3)	0.6615 (2)	0.1097 (12)
H20A	−0.4703	0.5760	0.6712	0.164*
H20B	−0.3508	0.5616	0.6054	0.164*
H20C	−0.3426	0.6414	0.6686	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0639 (4)	0.0605 (4)	0.0542 (3)	−0.0178 (3)	0.0103 (3)	−0.0063 (3)
O1	0.0513 (9)	0.0788 (11)	0.0467 (9)	0.0067 (8)	0.0047 (7)	0.0040 (8)
O2	0.1259 (17)	0.0482 (10)	0.0781 (13)	−0.0087 (10)	0.0276 (13)	−0.0058 (10)
O3	0.0632 (12)	0.1228 (17)	0.0865 (13)	−0.0377 (11)	0.0139 (10)	−0.0305 (14)
O4	0.0721 (10)	0.0594 (10)	0.0555 (10)	0.0228 (8)	0.0178 (8)	0.0063 (9)
O5	0.0932 (14)	0.0661 (12)	0.0762 (13)	0.0151 (10)	−0.0197 (11)	0.0193 (10)
O6	0.0838 (11)	0.0538 (10)	0.0495 (9)	0.0132 (9)	−0.0116 (8)	−0.0001 (8)
O7	0.0681 (12)	0.0765 (12)	0.0671 (12)	−0.0053 (9)	0.0197 (10)	−0.0090 (10)
O8	0.0785 (14)	0.1293 (19)	0.0832 (14)	0.0074 (13)	0.0282 (12)	−0.0074 (14)
N1	0.0599 (12)	0.0553 (12)	0.0501 (11)	0.0039 (10)	−0.0009 (9)	0.0037 (9)
C1	0.0752 (18)	0.0509 (13)	0.0508 (14)	0.0014 (13)	0.0123 (12)	−0.0048 (11)
C2	0.091 (2)	0.0660 (19)	0.111 (3)	−0.0071 (16)	0.040 (2)	0.0001 (19)
C3	0.172 (4)	0.067 (2)	0.158 (4)	−0.026 (3)	0.110 (4)	−0.011 (3)
C4	0.327 (9)	0.051 (2)	0.086 (3)	0.015 (4)	0.099 (5)	0.006 (2)
C5	0.284 (8)	0.072 (3)	0.063 (2)	0.047 (4)	0.000 (4)	0.005 (2)
C6	0.146 (3)	0.0672 (19)	0.0687 (19)	0.0207 (19)	−0.022 (2)	−0.0035 (17)
C7	0.0501 (13)	0.0562 (13)	0.0511 (13)	−0.0018 (10)	0.0042 (12)	−0.0031 (12)
C8	0.103 (2)	0.0783 (18)	0.0530 (15)	−0.0034 (17)	0.0046 (16)	−0.0068 (14)
C9	0.0544 (14)	0.0732 (17)	0.0449 (12)	0.0045 (13)	0.0020 (10)	0.0071 (13)
C10	0.0605 (14)	0.0505 (13)	0.0426 (12)	0.0122 (11)	0.0030 (11)	−0.0020 (10)
C11	0.0684 (16)	0.0535 (14)	0.0562 (15)	0.0158 (12)	0.0046 (13)	0.0027 (12)
C12	0.0800 (19)	0.0528 (15)	0.0709 (18)	0.0119 (14)	0.0089 (15)	0.0088 (14)
C13	0.091 (2)	0.0798 (19)	0.0543 (15)	0.0030 (17)	0.0198 (16)	0.0136 (14)
C14	0.095 (2)	0.087 (2)	0.0487 (15)	0.0202 (17)	0.0263 (15)	0.0026 (14)
C15	0.095 (2)	0.0631 (17)	0.0684 (18)	0.0118 (16)	−0.0278 (17)	0.0084 (14)
C16	0.075 (2)	0.087 (2)	0.141 (3)	0.0195 (17)	−0.036 (2)	0.010 (2)
C17	0.176 (4)	0.121 (3)	0.068 (2)	−0.001 (3)	−0.055 (2)	0.009 (2)
C18	0.0679 (18)	0.0804 (18)	0.0722 (18)	−0.0053 (15)	0.0199 (16)	0.0013 (16)
C19	0.117 (3)	0.091 (2)	0.158 (4)	−0.032 (2)	0.040 (3)	−0.005 (3)
C20	0.085 (2)	0.138 (3)	0.106 (3)	−0.005 (2)	−0.008 (2)	0.027 (3)

Geometric parameters (Å, º) top

S1—O3	1.411 (2)	C8—H8A	0.9600
S1—O2	1.419 (2)	C8—H8B	0.9600
S1—O1	1.5722 (17)	C8—H8C	0.9600
S1—N1	1.590 (2)	C9—C10	1.518 (3)
O1—C9	1.440 (3)	C9—H9A	0.9700
O4—C10	1.409 (3)	C9—H9B	0.9700
O4—C14	1.434 (3)	C10—C11	1.529 (3)
O5—C11	1.416 (3)	C11—C12	1.510 (4)
O5—C15	1.430 (3)	C11—H11	0.9800
O6—C10	1.406 (3)	C12—C13	1.535 (4)
O6—C15	1.443 (3)	C12—H12	0.9800
O7—C12	1.409 (3)	C13—C14	1.510 (4)
O7—C18	1.423 (3)	C13—H13	0.9800
O8—C13	1.408 (4)	C14—H14A	0.9700
O8—C18	1.411 (3)	C14—H14B	0.9700
N1—C7	1.485 (3)	C15—C16	1.496 (5)
N1—H1A	0.9275	C15—C17	1.519 (4)
C1—C6	1.358 (4)	C16—H16A	0.9600
C1—C2	1.375 (4)	C16—H16B	0.9600
C1—C7	1.509 (3)	C16—H16C	0.9600
C2—C3	1.383 (5)	C17—H17A	0.9600
C2—H2	0.9300	C17—H17B	0.9600
C3—C4	1.349 (8)	C17—H17C	0.9600
C3—H3	0.9300	C18—C20	1.483 (4)
C4—C5	1.350 (8)	C18—C19	1.516 (5)
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.387 (6)	C19—H19B	0.9600
C5—H5	0.9300	C19—H19C	0.9600
C6—H6	0.9300	C20—H20A	0.9600
C7—C8	1.514 (4)	C20—H20B	0.9600
C7—H7	0.9800	C20—H20C	0.9600

O3—S1—O2	121.23 (14)	C12—C11—C10	113.8 (2)
O3—S1—O1	102.63 (12)	O5—C11—H11	110.0
O2—S1—O1	108.03 (11)	C12—C11—H11	110.0
O3—S1—N1	108.09 (11)	C10—C11—H11	110.0
O2—S1—N1	107.80 (13)	O7—C12—C11	106.9 (2)
O1—S1—N1	108.49 (10)	O7—C12—C13	103.0 (2)
C9—O1—S1	118.64 (14)	C11—C12—C13	114.3 (2)
C10—O4—C14	113.32 (19)	O7—C12—H12	110.8
C11—O5—C15	106.29 (19)	C11—C12—H12	110.8
C10—O6—C15	110.64 (19)	C13—C12—H12	110.8
C12—O7—C18	108.9 (2)	O8—C13—C14	112.1 (3)
C13—O8—C18	110.8 (2)	O8—C13—C12	104.3 (2)
C7—N1—S1	122.60 (16)	C14—C13—C12	111.2 (2)
C7—N1—H1A	126.9	O8—C13—H13	109.7
S1—N1—H1A	104.9	C14—C13—H13	109.7
C6—C1—C2	118.9 (3)	C12—C13—H13	109.7
C6—C1—C7	120.4 (3)	O4—C14—C13	111.3 (2)
C2—C1—C7	120.6 (3)	O4—C14—H14A	109.4
C1—C2—C3	119.9 (4)	C13—C14—H14A	109.4
C1—C2—H2	120.1	O4—C14—H14B	109.4
C3—C2—H2	120.1	C13—C14—H14B	109.4
C4—C3—C2	120.7 (5)	H14A—C14—H14B	108.0
C4—C3—H3	119.7	O5—C15—O6	103.9 (2)
C2—C3—H3	119.7	O5—C15—C16	111.8 (3)
C5—C4—C3	119.8 (5)	O6—C15—C16	110.4 (2)
C5—C4—H4	120.1	O5—C15—C17	108.8 (3)
C3—C4—H4	120.1	O6—C15—C17	108.1 (3)
C4—C5—C6	120.3 (5)	C16—C15—C17	113.4 (3)
C4—C5—H5	119.8	C15—C16—H16A	109.5
C6—C5—H5	119.8	C15—C16—H16B	109.5
C1—C6—C5	120.4 (4)	H16A—C16—H16B	109.5
C1—C6—H6	119.8	C15—C16—H16C	109.5
C5—C6—H6	119.8	H16A—C16—H16C	109.5
N1—C7—C1	112.74 (18)	H16B—C16—H16C	109.5
N1—C7—C8	107.7 (2)	C15—C17—H17A	109.5
C1—C7—C8	113.1 (2)	C15—C17—H17B	109.5
N1—C7—H7	107.7	H17A—C17—H17B	109.5
C1—C7—H7	107.7	C15—C17—H17C	109.5
C8—C7—H7	107.7	H17A—C17—H17C	109.5
C7—C8—H8A	109.5	H17B—C17—H17C	109.5
C7—C8—H8B	109.5	O8—C18—O7	105.7 (2)
H8A—C8—H8B	109.5	O8—C18—C20	109.2 (3)
C7—C8—H8C	109.5	O7—C18—C20	108.2 (2)
H8A—C8—H8C	109.5	O8—C18—C19	108.6 (3)
H8B—C8—H8C	109.5	O7—C18—C19	109.9 (3)
O1—C9—C10	108.12 (18)	C20—C18—C19	114.8 (3)
O1—C9—H9A	110.1	C18—C19—H19A	109.5
C10—C9—H9A	110.1	C18—C19—H19B	109.5
O1—C9—H9B	110.1	H19A—C19—H19B	109.5
C10—C9—H9B	110.1	C18—C19—H19C	109.5
H9A—C9—H9B	108.4	H19A—C19—H19C	109.5
O6—C10—O4	110.70 (18)	H19B—C19—H19C	109.5
O6—C10—C9	110.3 (2)	C18—C20—H20A	109.5
O4—C10—C9	102.21 (18)	C18—C20—H20B	109.5
O6—C10—C11	103.55 (19)	H20A—C20—H20B	109.5
O4—C10—C11	113.6 (2)	C18—C20—H20C	109.5
C9—C10—C11	116.6 (2)	H20A—C20—H20C	109.5
O5—C11—C12	108.8 (2)	H20B—C20—H20C	109.5
O5—C11—C10	104.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.93	2.06	2.959 (3)	163

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₉NO₈S
M_r	443.50
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.5733 (9), 15.0134 (14), 15.9462 (15)
V (Å³)	2291.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.28 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	13609, 4041, 3348
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.04
No. of reflections	4041
No. of parameters	276
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19
Absolute structure	Flack (1983), 1736 Friedel pairs
Absolute structure parameter	−0.02 (8)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.93	2.06	2.959 (3)	162.9

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

Acknowledgements

This work was supported by the program of the Education Department of Liaoning Province (No. L2010533), and the program of the Science and Technology Department of Liaoning Province, China (No. 2009226015–5).

References

Bruker (2007). SMART and SAINT. 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
Maryanoff, B. E. (2009). J. Med. Chem. 52, 3431–3440. Web of Science CrossRef PubMed CAS Google Scholar
Maryanoff, B. E., Costanzo, M. J., Nortey, S. O., Greco, M. N., Shank, R. P., Schupsky, J. J., Ortegon, M. P. & Vaught, J. L. (1998). J. Med. Chem. 41, 1315–1343. Web of Science CSD CrossRef CAS PubMed Google Scholar
Maryanoff, B. E., McComsey, D. F., Lee, J., Smith-Swintosky, V. L., Wang, Y.-P., Minor, L. K. & Todd, M. J. (2008). J. Med. Chem. 51, 2518–2521. Web of Science CrossRef PubMed 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
Winum, J., Temperini, C., Cheikh, K. E., Innocenti, A., Vullo, D., Ciattini, S., Montero, J., Scozzafava, A. & Supuran, C. T. (2006). J. Med. Chem. 49, 7024–7031. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 5| May 2012| Page o1581

doi:10.1107/S1600536812016704

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

[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetra­methyl­tetra­hydro-3aH-bis­­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-3a-yl]methyl (R)-N-(1-phenyl­eth­yl)sulfamate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-3a-yl]methyl (R)-N-(1-phenylethyl)sulfamate