(Z)-1,2:5,6-Di-O-isopropyl-idene-α-d-ribo-hexofuranos-3-ulose O-benzyl-oxime.

The title compound, C(19)H(25)NO(6), is a Z diastereomer in which the phenyl ring of the 3-benzyl-oxime substituent and the 5,6-O-isopropyl-idene acetal are both located on the Si-face of the C=N double bond. Inter-molecular C-H⋯O inter-actions result in helical chains along the b axis of the monoclinic unit cell.

Related literature

For background to sugar-based oxime derivatives, see: Tronchet et al. (1979 ▶, 1981 ▶, 1989 ▶); Peri et al. (2004 ▶). For the synthesis, see: Plenkiewicz et al. (1974 ▶); Fernández-González & Alonso (2006 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For C–H⋯O inter­actions, see: Gatti et al. (2002 ▶). For the synthesis of a reactant, see: Shing et al. (1996 ▶).

Experimental

Crystal data

C19H25NO6

M = 363.40

Monoclinic,

a = 11.8012 (12) Å

b = 6.0019 (5) Å

c = 13.7021 (11) Å

β = 95.122 (11)°

V = 966.64 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.05 × 0.04 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: none

9449 measured reflections

2558 independent reflections

2023 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.131

S = 0.99

2558 reflections

235 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 1997 ▶); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1990 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶), XP and SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006333/ng2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006333/ng2545Isup2.hkl

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

C19H25NO6	F(000) = 388
Mr = 363.40	Dx = 1.249 Mg m−3
Monoclinic, P21	Melting point: 403(1) K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.8012 (12) Å	Cell parameters from 1353 reflections
b = 6.0019 (5) Å	θ = 1.9–28.2°
c = 13.7021 (11) Å	µ = 0.09 mm−1
β = 95.122 (11)°	T = 293 K
V = 966.64 (15) Å3	Prism, colourless
Z = 2	0.30 × 0.05 × 0.04 mm

Stoe IPDS diffractometer	2023 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
graphite	θmax = 28.2°, θmin = 3.0°
Detector resolution: 6.0 pixels mm-1	h = −15→15
φ scans	k = −7→7
9449 measured reflections	l = −18→17
2558 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0808P)2] where P = (Fo2 + 2Fc2)/3
2558 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

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 > 2σ (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
N1	−0.06053 (17)	0.2232 (4)	0.27810 (14)	0.0389 (4)
O1	0.02900 (13)	0.5554 (3)	0.09073 (11)	0.0389 (4)
O2	0.11981 (15)	0.8375 (3)	0.18283 (13)	0.0445 (4)
O3	0.07981 (16)	0.6561 (4)	0.32044 (12)	0.0510 (5)
O4	−0.06093 (18)	0.2884 (3)	0.37689 (13)	0.0477 (4)
O5	−0.21517 (14)	0.5609 (3)	0.09506 (14)	0.0469 (4)
O6	−0.34050 (19)	0.2785 (5)	0.0706 (3)	0.1008 (12)
C1	0.01554 (19)	0.7319 (4)	0.15833 (17)	0.0371 (5)
H1	−0.0423	0.8385	0.1321	0.044*
C2	−0.01695 (19)	0.6276 (4)	0.25278 (17)	0.0363 (5)
H2	−0.0841	0.7001	0.2758	0.044*
C3	−0.04108 (17)	0.3891 (4)	0.22521 (16)	0.0325 (4)
C4	−0.03742 (18)	0.3679 (4)	0.11580 (16)	0.0334 (4)
H4	0.0012	0.2294	0.1004	0.040*
C5	−0.15390 (19)	0.3778 (4)	0.05929 (18)	0.0384 (5)
H5	−0.1455	0.3985	−0.0106	0.046*
C6	−0.2320 (2)	0.1834 (5)	0.0731 (3)	0.0554 (7)
H6A	−0.2283	0.0754	0.0208	0.067*
H6B	−0.2119	0.1103	0.1354	0.067*
C7	0.1722 (2)	0.7382 (5)	0.27004 (19)	0.0457 (6)
C8	0.2295 (3)	0.9206 (6)	0.3320 (3)	0.0664 (9)
H8A	0.2656	0.8576	0.3913	0.100*
H8B	0.1738	1.0280	0.3479	0.100*
H8C	0.2857	0.9922	0.2963	0.100*
C9	0.2493 (3)	0.5495 (8)	0.2465 (3)	0.0773 (10)
H9A	0.2837	0.4860	0.3063	0.116*
H9B	0.3076	0.6048	0.2084	0.116*
H9C	0.2058	0.4375	0.2099	0.116*
C10	−0.0865 (2)	0.0973 (5)	0.43327 (18)	0.0494 (6)
H10A	−0.0655	0.1285	0.5020	0.059*
H10B	−0.0403	−0.0266	0.4146	0.059*
C11	−0.2096 (2)	0.0296 (5)	0.42074 (18)	0.0452 (6)
C12	−0.2392 (3)	−0.1738 (7)	0.4566 (4)	0.0787 (12)
H12	−0.1830	−0.2674	0.4856	0.094*
C13	−0.3520 (3)	−0.2411 (8)	0.4502 (4)	0.0966 (15)
H13	−0.3711	−0.3789	0.4751	0.116*
C14	−0.4337 (3)	−0.1078 (10)	0.4081 (4)	0.0921 (14)
H14	−0.5095	−0.1515	0.4058	0.111*
C15	−0.4060 (3)	0.0900 (11)	0.3690 (5)	0.114 (2)
H15	−0.4623	0.1795	0.3376	0.137*
C16	−0.2925 (3)	0.1590 (7)	0.3761 (3)	0.0835 (12)
H16	−0.2738	0.2956	0.3498	0.100*
C17	−0.3326 (2)	0.5127 (6)	0.0709 (3)	0.0613 (8)
C18	−0.3984 (3)	0.6133 (11)	0.1487 (4)	0.1084 (18)
H18A	−0.3931	0.7728	0.1458	0.163*
H18B	−0.3674	0.5623	0.2119	0.163*
H18C	−0.4767	0.5693	0.1380	0.163*
C19	−0.3701 (3)	0.5986 (8)	−0.0303 (3)	0.0872 (12)
H19A	−0.3649	0.7582	−0.0307	0.131*
H19B	−0.4473	0.5545	−0.0481	0.131*
H19C	−0.3218	0.5378	−0.0765	0.131*

	U11	U22	U33	U12	U13	U23
N1	0.0444 (10)	0.0412 (10)	0.0313 (9)	−0.0039 (8)	0.0040 (8)	−0.0003 (8)
O1	0.0417 (8)	0.0452 (9)	0.0306 (7)	−0.0071 (7)	0.0083 (6)	0.0006 (7)
O2	0.0443 (9)	0.0466 (10)	0.0421 (9)	−0.0176 (7)	0.0019 (7)	0.0041 (8)
O3	0.0495 (9)	0.0706 (12)	0.0317 (8)	−0.0259 (9)	−0.0027 (7)	0.0008 (8)
O4	0.0652 (11)	0.0476 (9)	0.0312 (8)	−0.0141 (8)	0.0090 (8)	−0.0014 (7)
O5	0.0343 (8)	0.0513 (10)	0.0536 (10)	0.0019 (8)	−0.0047 (7)	−0.0090 (9)
O6	0.0367 (10)	0.0663 (15)	0.199 (4)	−0.0063 (11)	0.0061 (15)	0.0190 (19)
C1	0.0360 (10)	0.0364 (10)	0.0383 (12)	−0.0056 (9)	0.0007 (9)	0.0028 (10)
C2	0.0349 (10)	0.0418 (11)	0.0323 (11)	−0.0041 (9)	0.0042 (8)	−0.0050 (9)
C3	0.0275 (9)	0.0375 (10)	0.0324 (11)	0.0007 (8)	0.0023 (8)	−0.0014 (9)
C4	0.0361 (10)	0.0327 (10)	0.0317 (10)	−0.0012 (8)	0.0050 (8)	−0.0017 (9)
C5	0.0398 (11)	0.0413 (11)	0.0335 (11)	−0.0010 (10)	−0.0002 (9)	−0.0070 (10)
C6	0.0411 (12)	0.0512 (15)	0.0721 (19)	−0.0080 (12)	−0.0050 (13)	−0.0109 (14)
C7	0.0400 (12)	0.0549 (14)	0.0416 (13)	−0.0101 (11)	0.0001 (10)	0.0039 (12)
C8	0.0580 (16)	0.077 (2)	0.0614 (19)	−0.0270 (16)	−0.0088 (15)	−0.0039 (16)
C9	0.0561 (17)	0.089 (3)	0.086 (2)	0.0134 (19)	−0.0004 (17)	0.001 (2)
C10	0.0557 (14)	0.0593 (16)	0.0330 (12)	−0.0121 (13)	0.0026 (10)	0.0076 (12)
C11	0.0511 (13)	0.0508 (14)	0.0350 (11)	−0.0015 (11)	0.0108 (10)	0.0022 (11)
C12	0.0552 (17)	0.073 (2)	0.108 (3)	−0.0078 (16)	0.0104 (18)	0.038 (2)
C13	0.061 (2)	0.089 (3)	0.141 (4)	−0.019 (2)	0.015 (2)	0.039 (3)
C14	0.0490 (17)	0.114 (3)	0.115 (4)	−0.004 (2)	0.016 (2)	0.008 (3)
C15	0.0470 (18)	0.126 (4)	0.169 (5)	0.019 (2)	0.009 (2)	0.051 (4)
C16	0.0572 (18)	0.075 (2)	0.119 (3)	0.0096 (17)	0.017 (2)	0.036 (2)
C17	0.0320 (11)	0.0644 (18)	0.086 (2)	0.0029 (12)	−0.0023 (12)	0.0015 (17)
C18	0.060 (2)	0.151 (5)	0.118 (4)	0.038 (3)	0.028 (2)	0.013 (4)
C19	0.0623 (18)	0.092 (3)	0.100 (3)	0.007 (2)	−0.0366 (19)	0.001 (2)

N1—C3	1.265 (3)	C8—H8B	0.9600
N1—O4	1.410 (3)	C8—H8C	0.9600
O1—C1	1.425 (3)	C9—H9A	0.9600
O1—C4	1.431 (3)	C9—H9B	0.9600
O2—C1	1.398 (3)	C9—H9C	0.9600
O2—C7	1.426 (3)	C10—C11	1.504 (4)
O3—C2	1.416 (3)	C10—H10A	0.9700
O3—C7	1.429 (3)	C10—H10B	0.9700
O4—C10	1.430 (3)	C11—C16	1.352 (4)
O5—C17	1.426 (3)	C11—C12	1.373 (5)
O5—C5	1.426 (3)	C12—C13	1.386 (5)
O6—C6	1.400 (4)	C12—H12	0.9300
O6—C17	1.409 (4)	C13—C14	1.343 (7)
C1—C2	1.518 (3)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.354 (7)
C2—C3	1.501 (3)	C14—H14	0.9300
C2—H2	0.9800	C15—C16	1.397 (6)
C3—C4	1.509 (3)	C15—H15	0.9300
C4—C5	1.517 (3)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.501 (6)
C5—C6	1.509 (4)	C17—C19	1.508 (5)
C5—H5	0.9800	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600
C7—C9	1.506 (5)	C19—H19A	0.9600
C7—C8	1.508 (4)	C19—H19B	0.9600
C8—H8A	0.9600	C19—H19C	0.9600
C3—N1—O4	110.36 (19)	H8A—C8—H8C	109.5
C1—O1—C4	109.48 (16)	H8B—C8—H8C	109.5
C1—O2—C7	108.55 (18)	C7—C9—H9A	109.5
C2—O3—C7	109.31 (17)	C7—C9—H9B	109.5
N1—O4—C10	108.36 (18)	H9A—C9—H9B	109.5
C17—O5—C5	106.0 (2)	C7—C9—H9C	109.5
C6—O6—C17	110.3 (2)	H9A—C9—H9C	109.5
O2—C1—O1	110.25 (18)	H9B—C9—H9C	109.5
O2—C1—C2	105.44 (18)	O4—C10—C11	113.8 (2)
O1—C1—C2	107.37 (19)	O4—C10—H10A	108.8
O2—C1—H1	111.2	C11—C10—H10A	108.8
O1—C1—H1	111.2	O4—C10—H10B	108.8
C2—C1—H1	111.2	C11—C10—H10B	108.8
O3—C2—C3	113.8 (2)	H10A—C10—H10B	107.7
O3—C2—C1	104.96 (18)	C16—C11—C12	118.4 (3)
C3—C2—C1	103.64 (19)	C16—C11—C10	123.3 (3)
O3—C2—H2	111.3	C12—C11—C10	118.3 (3)
C3—C2—H2	111.3	C11—C12—C13	120.6 (4)
C1—C2—H2	111.3	C11—C12—H12	119.7
N1—C3—C2	130.3 (2)	C13—C12—H12	119.7
N1—C3—C4	121.7 (2)	C14—C13—C12	120.2 (4)
C2—C3—C4	107.98 (19)	C14—C13—H13	119.9
O1—C4—C3	103.72 (17)	C12—C13—H13	119.9
O1—C4—C5	109.72 (18)	C13—C14—C15	120.2 (4)
C3—C4—C5	113.50 (18)	C13—C14—H14	119.9
O1—C4—H4	109.9	C15—C14—H14	119.9
C3—C4—H4	109.9	C14—C15—C16	119.8 (4)
C5—C4—H4	109.9	C14—C15—H15	120.1
O5—C5—C6	102.63 (19)	C16—C15—H15	120.1
O5—C5—C4	108.59 (18)	C11—C16—C15	120.8 (4)
C6—C5—C4	116.2 (2)	C11—C16—H16	119.6
O5—C5—H5	109.7	C15—C16—H16	119.6
C6—C5—H5	109.7	O6—C17—O5	105.4 (2)
C4—C5—H5	109.7	O6—C17—C18	111.4 (4)
O6—C6—C5	104.4 (2)	O5—C17—C18	107.9 (3)
O6—C6—H6A	110.9	O6—C17—C19	109.0 (4)
C5—C6—H6A	110.9	O5—C17—C19	110.1 (3)
O6—C6—H6B	110.9	C18—C17—C19	112.8 (3)
C5—C6—H6B	110.9	C17—C18—H18A	109.5
H6A—C6—H6B	108.9	C17—C18—H18B	109.5
O2—C7—O3	104.90 (19)	H18A—C18—H18B	109.5
O2—C7—C9	111.1 (3)	C17—C18—H18C	109.5
O3—C7—C9	110.2 (3)	H18A—C18—H18C	109.5
O2—C7—C8	107.9 (2)	H18B—C18—H18C	109.5
O3—C7—C8	107.6 (2)	C17—C19—H19A	109.5
C9—C7—C8	114.6 (3)	C17—C19—H19B	109.5
C7—C8—H8A	109.5	H19A—C19—H19B	109.5
C7—C8—H8B	109.5	C17—C19—H19C	109.5
H8A—C8—H8B	109.5	H19A—C19—H19C	109.5
C7—C8—H8C	109.5	H19B—C19—H19C	109.5
C3—N1—O4—C10	178.3 (2)	C3—C4—C5—C6	−68.1 (3)
C7—O2—C1—O1	−93.8 (2)	C17—O6—C6—C5	−8.4 (4)
C7—O2—C1—C2	21.8 (3)	O5—C5—C6—O6	25.7 (3)
C4—O1—C1—O2	139.51 (18)	C4—C5—C6—O6	144.0 (3)
C4—O1—C1—C2	25.1 (2)	C1—O2—C7—O3	−27.2 (3)
C7—O3—C2—C3	104.1 (2)	C1—O2—C7—C9	91.9 (3)
C7—O3—C2—C1	−8.6 (3)	C1—O2—C7—C8	−141.6 (2)
O2—C1—C2—O3	−8.0 (3)	C2—O3—C7—O2	21.7 (3)
O1—C1—C2—O3	109.5 (2)	C2—O3—C7—C9	−98.0 (3)
O2—C1—C2—C3	−127.70 (19)	C2—O3—C7—C8	136.4 (2)
O1—C1—C2—C3	−10.1 (2)	N1—O4—C10—C11	−74.9 (3)
O4—N1—C3—C2	1.8 (3)	O4—C10—C11—C16	−12.1 (4)
O4—N1—C3—C4	−179.14 (19)	O4—C10—C11—C12	168.0 (3)
O3—C2—C3—N1	58.5 (3)	C16—C11—C12—C13	−2.2 (7)
C1—C2—C3—N1	172.0 (2)	C10—C11—C12—C13	177.7 (4)
O3—C2—C3—C4	−120.6 (2)	C11—C12—C13—C14	0.4 (8)
C1—C2—C3—C4	−7.2 (2)	C12—C13—C14—C15	2.0 (9)
C1—O1—C4—C3	−28.9 (2)	C13—C14—C15—C16	−2.5 (9)
C1—O1—C4—C5	92.7 (2)	C12—C11—C16—C15	1.7 (7)
N1—C3—C4—O1	−157.54 (19)	C10—C11—C16—C15	−178.2 (5)
C2—C3—C4—O1	21.7 (2)	C14—C15—C16—C11	0.6 (9)
N1—C3—C4—C5	83.5 (3)	C6—O6—C17—O5	−12.4 (5)
C2—C3—C4—C5	−97.3 (2)	C6—O6—C17—C18	−129.1 (4)
C17—O5—C5—C6	−33.8 (3)	C6—O6—C17—C19	105.8 (4)
C17—O5—C5—C4	−157.3 (2)	C5—O5—C17—O6	29.4 (4)
O1—C4—C5—O5	−68.6 (2)	C5—O5—C17—C18	148.5 (3)
C3—C4—C5—O5	46.9 (3)	C5—O5—C17—C19	−88.0 (3)
O1—C4—C5—C6	176.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.98	2.43	3.386 (3)	164
C10—H10A···O3ii	0.97	2.46	3.387 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.98	2.43	3.386 (3)	164
C10—H10A⋯O3ii	0.97	2.46	3.387 (3)	160

Symmetry codes: (i) ; (ii) .