[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetra-methyl-tetra-hydro-3aH-bis-[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl (R)-N-(1-phenyl-eth-yl)sulfamate.

In the title compound, C(20)H(29)NO(8)S, 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, mol-ecules are linked by N-H⋯O hydrogen bonds into a supra-molecular 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 = 443.50

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.04

4041 reflections

276 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1736 Friedel pairs

Flack parameter: −0.02 (8)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016704/xu5509sup1.cif

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

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

C20H29NO8S	Dx = 1.285 Mg m−3
Mr = 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

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

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(Fo2) + (0.0565P)2 + 0.0232P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4041 reflections	Δρmax = 0.14 e Å−3
276 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1736 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (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	0.19640 (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*

	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)

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)

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

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) .