Glucosyl anthranilate.

In the crystal structure of the title compound, C(21)H(25)NO(11), the hexopyranosyl ring adopts a chair conformation and the five substituents are in equatorial positions. An intra-molecular hydrogen bond between the amino group and a neighbouring carbonyl group is found. Two carbonyl groups are disordered and were refined using a split model.

Related literature

The title compound was first obtained by Robert & Tabone (1953 ▶). For the glycosyl­ation reaction of N-hydroxy­phthalimide, see: Cao et al. (1995 ▶); Saulius et al. (2005 ▶). For the Hofmann rearrangement, see: Aspinall (1941 ▶); Yu et al. (2001 ▶).

Experimental

Crystal data

C21H25NO11

M = 467.42

Triclinic,

a = 5.8220 (12) Å

b = 9.1210 (18) Å

c = 11.131 (2) Å

α = 98.94 (3)°

β = 94.53 (3)°

γ = 90.22 (3)°

V = 582.0 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2321 measured reflections

2096 independent reflections

1783 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 1.04

2096 reflections

320 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040975/nc2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040975/nc2157Isup2.hkl

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

C21H25NO11	Z = 1
Mr = 467.42	F(000) = 246
Triclinic, P1	Dx = 1.334 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8220 (12) Å	Cell parameters from 25 reflections
b = 9.1210 (18) Å	θ = 9–12°
c = 11.131 (2) Å	µ = 0.11 mm−1
α = 98.94 (3)°	T = 293 K
β = 94.53 (3)°	Block, colourless
γ = 90.22 (3)°	0.30 × 0.20 × 0.10 mm
V = 582.0 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 25.3°, θmin = 1.9°
graphite	h = 0→6
ω/2θ scans	k = −10→10
2321 measured reflections	l = −13→13
2096 independent reflections	3 standard reflections every 200 reflections
1783 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.0615P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2096 reflections	Δρmin = −0.13 e Å−3
320 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
5 restraints	Extinction coefficient: 0.052 (8)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
O1	0.4723 (4)	0.2186 (3)	0.0201 (2)	0.0473 (6)
O2	0.4296 (4)	0.0007 (3)	−0.1971 (2)	0.0552 (6)
O3	0.6518 (6)	−0.1311 (4)	−0.3260 (4)	0.1014 (13)
O4	0.6863 (4)	0.4159 (3)	−0.2092 (2)	0.0478 (6)
O5	1.0705 (5)	0.4424 (4)	−0.1993 (3)	0.0797 (9)
O6	0.8323 (4)	0.6042 (3)	0.0311 (2)	0.0539 (6)
O7	0.6443 (18)	0.8007 (11)	−0.0182 (10)	0.089 (3)	0.50
O7'	0.697 (2)	0.7638 (13)	−0.0826 (9)	0.102 (4)	0.50
O8	0.4552 (5)	0.5912 (3)	0.1864 (2)	0.0642 (7)
O9	0.715 (3)	0.587 (3)	0.337 (2)	0.172 (11)	0.50
O9'	0.650 (4)	0.562 (2)	0.3641 (18)	0.138 (8)	0.50
O10	0.3348 (4)	0.2984 (3)	0.2025 (2)	0.0538 (6)
O11	−0.0099 (4)	0.2080 (3)	0.1202 (2)	0.0613 (7)
N1	−0.2584 (6)	0.0580 (5)	0.2582 (4)	0.0830 (11)
H1A	−0.3743	0.0071	0.2734	0.100*
H1B	−0.2509	0.0817	0.1868	0.100*
C1	0.3810 (6)	0.3425 (4)	0.0908 (3)	0.0468 (8)
H1C	0.2406	0.3758	0.0493	0.056*
C2	0.5594 (6)	0.4647 (4)	0.1187 (3)	0.0498 (8)
H2A	0.6935	0.4331	0.1665	0.060*
C3	0.6312 (5)	0.5090 (4)	0.0013 (3)	0.0447 (8)
H3A	0.5061	0.5628	−0.0360	0.054*
C4	0.6931 (5)	0.3744 (4)	−0.0887 (3)	0.0442 (8)
H4A	0.8474	0.3406	−0.0653	0.053*
C5	0.5175 (6)	0.2470 (4)	−0.0987 (3)	0.0423 (7)
H5A	0.3740	0.2725	−0.1423	0.051*
C6	0.6126 (6)	0.1085 (4)	−0.1660 (3)	0.0498 (8)
H6A	0.6767	0.1297	−0.2395	0.060*
H6B	0.7344	0.0707	−0.1152	0.060*
C7	0.4769 (8)	−0.1189 (5)	−0.2748 (4)	0.0656 (11)
C8	0.2885 (9)	−0.2322 (5)	−0.2932 (5)	0.0827 (14)
H8A	0.2755	−0.2799	−0.3767	0.124*
H8B	0.1459	−0.1852	−0.2739	0.124*
H8C	0.3223	−0.3049	−0.2407	0.124*
C9	0.8873 (6)	0.4456 (4)	−0.2551 (3)	0.0527 (9)
C10	0.8433 (8)	0.4856 (5)	−0.3784 (4)	0.0667 (11)
H10A	0.7942	0.5867	−0.3718	0.100*
H10B	0.7251	0.4214	−0.4236	0.100*
H10C	0.9822	0.4748	−0.4199	0.100*
C11	0.8326 (8)	0.7376 (4)	−0.0001 (4)	0.0644 (10)
C12	1.0535 (8)	0.8176 (5)	0.0358 (5)	0.0797 (13)
H12A	1.0286	0.9226	0.0444	0.120*	0.50
H12B	1.1587	0.7897	−0.0256	0.120*	0.50
H12C	1.1172	0.7928	0.1122	0.120*	0.50
H12D	1.1744	0.7475	0.0429	0.120*	0.50
H12E	1.0443	0.8804	0.1129	0.120*	0.50
H12F	1.0858	0.8773	−0.0249	0.120*	0.50
C13	0.5261 (15)	0.6275 (7)	0.3044 (5)	0.104 (2)
C14	0.3672 (15)	0.7450 (8)	0.3642 (6)	0.140 (3)
H14A	0.4208	0.7742	0.4483	0.210*
H14B	0.2135	0.7048	0.3589	0.210*
H14C	0.3675	0.8299	0.3229	0.210*
C15	0.1294 (6)	0.2281 (4)	0.2076 (3)	0.0463 (8)
C16	0.1078 (6)	0.1823 (4)	0.3258 (3)	0.0509 (8)
C17	0.2779 (7)	0.2219 (5)	0.4221 (3)	0.0662 (11)
H17A	0.4059	0.2771	0.4093	0.079*
C18	0.2601 (8)	0.1814 (6)	0.5343 (4)	0.0797 (13)
H18A	0.3756	0.2077	0.5967	0.096*
C19	0.0679 (8)	0.1007 (6)	0.5540 (4)	0.0797 (13)
H19A	0.0542	0.0727	0.6300	0.096*
C20	−0.0983 (8)	0.0629 (5)	0.4637 (4)	0.0734 (12)
H20A	−0.2259	0.0093	0.4792	0.088*
C21	−0.0876 (6)	0.1010 (5)	0.3469 (4)	0.0598 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0441 (13)	0.0510 (13)	0.0484 (14)	−0.0033 (10)	0.0031 (10)	0.0132 (11)
O2	0.0537 (14)	0.0508 (14)	0.0595 (15)	−0.0097 (11)	0.0062 (11)	0.0030 (12)
O3	0.103 (3)	0.079 (2)	0.117 (3)	−0.0201 (19)	0.056 (2)	−0.026 (2)
O4	0.0410 (12)	0.0614 (14)	0.0442 (13)	−0.0013 (10)	0.0038 (10)	0.0185 (10)
O5	0.0482 (16)	0.115 (3)	0.085 (2)	0.0004 (16)	0.0113 (14)	0.0408 (19)
O6	0.0488 (13)	0.0473 (13)	0.0660 (15)	−0.0081 (10)	−0.0006 (11)	0.0135 (11)
O7	0.097 (6)	0.059 (5)	0.111 (8)	−0.001 (4)	−0.026 (6)	0.027 (6)
O7'	0.137 (9)	0.074 (7)	0.097 (7)	−0.030 (6)	−0.043 (7)	0.048 (6)
O8	0.0817 (19)	0.0653 (17)	0.0434 (14)	−0.0074 (14)	0.0076 (13)	0.0007 (12)
O9	0.195 (14)	0.25 (2)	0.054 (10)	−0.041 (14)	−0.044 (11)	−0.003 (10)
O9'	0.24 (2)	0.120 (9)	0.045 (7)	0.027 (12)	−0.037 (9)	0.012 (6)
O10	0.0464 (13)	0.0762 (17)	0.0416 (13)	−0.0096 (12)	0.0003 (10)	0.0195 (12)
O11	0.0465 (13)	0.0835 (18)	0.0562 (15)	−0.0085 (12)	−0.0038 (12)	0.0225 (13)
N1	0.056 (2)	0.113 (3)	0.084 (3)	−0.024 (2)	0.0081 (19)	0.029 (2)
C1	0.0431 (18)	0.057 (2)	0.0412 (18)	−0.0010 (16)	0.0010 (14)	0.0115 (16)
C2	0.053 (2)	0.055 (2)	0.0421 (17)	−0.0015 (16)	−0.0016 (15)	0.0115 (16)
C3	0.0415 (18)	0.0468 (19)	0.0463 (19)	−0.0008 (15)	−0.0011 (14)	0.0115 (15)
C4	0.0395 (17)	0.051 (2)	0.0440 (18)	−0.0010 (15)	−0.0026 (14)	0.0153 (15)
C5	0.0365 (16)	0.0510 (19)	0.0408 (17)	−0.0019 (14)	0.0005 (13)	0.0127 (14)
C6	0.0476 (19)	0.052 (2)	0.0501 (19)	−0.0045 (16)	0.0055 (15)	0.0068 (16)
C7	0.083 (3)	0.055 (2)	0.057 (2)	−0.010 (2)	0.007 (2)	0.0042 (19)
C8	0.099 (4)	0.064 (3)	0.080 (3)	−0.028 (3)	0.008 (3)	−0.005 (2)
C9	0.050 (2)	0.052 (2)	0.059 (2)	−0.0008 (16)	0.0101 (18)	0.0132 (17)
C10	0.074 (3)	0.074 (3)	0.056 (2)	−0.011 (2)	0.014 (2)	0.019 (2)
C11	0.076 (3)	0.050 (2)	0.069 (3)	−0.007 (2)	0.001 (2)	0.0158 (19)
C12	0.081 (3)	0.059 (3)	0.099 (4)	−0.020 (2)	0.016 (3)	0.007 (2)
C13	0.152 (6)	0.099 (4)	0.052 (3)	−0.029 (4)	−0.004 (4)	−0.006 (3)
C14	0.209 (8)	0.121 (5)	0.081 (4)	−0.021 (5)	0.050 (5)	−0.032 (4)
C15	0.0416 (18)	0.049 (2)	0.0492 (19)	0.0038 (15)	0.0062 (15)	0.0104 (15)
C16	0.047 (2)	0.059 (2)	0.050 (2)	0.0088 (16)	0.0126 (16)	0.0149 (17)
C17	0.061 (2)	0.093 (3)	0.048 (2)	−0.001 (2)	0.0040 (18)	0.021 (2)
C18	0.069 (3)	0.121 (4)	0.053 (2)	0.005 (3)	0.006 (2)	0.028 (2)
C19	0.080 (3)	0.112 (4)	0.060 (3)	0.023 (3)	0.026 (2)	0.041 (2)
C20	0.067 (3)	0.086 (3)	0.078 (3)	0.004 (2)	0.031 (2)	0.034 (2)
C21	0.045 (2)	0.070 (2)	0.069 (2)	0.0069 (18)	0.0152 (18)	0.021 (2)

O1—C1	1.405 (4)	C6—H6A	0.9700
O1—C5	1.430 (4)	C6—H6B	0.9700
O2—C7	1.326 (5)	C7—C8	1.485 (6)
O2—C6	1.432 (4)	C8—H8A	0.9600
O3—C7	1.203 (5)	C8—H8B	0.9600
O4—C9	1.356 (4)	C8—H8C	0.9600
O4—C4	1.447 (4)	C9—C10	1.478 (5)
O5—C9	1.194 (4)	C10—H10A	0.9600
O6—C11	1.316 (4)	C10—H10B	0.9600
O6—C3	1.441 (4)	C10—H10C	0.9600
O7—C11	1.257 (10)	C11—C12	1.472 (6)
O7'—C11	1.217 (9)	C12—H12A	0.9600
O8—C13	1.335 (6)	C12—H12B	0.9600
O8—C2	1.440 (5)	C12—H12C	0.9600
O9—C13	1.204 (17)	C12—H12D	0.9600
O9'—C13	1.169 (14)	C12—H12E	0.9600
O10—C15	1.364 (4)	C12—H12F	0.9600
O10—C1	1.409 (4)	C13—C14	1.526 (11)
O11—C15	1.206 (4)	C14—H14A	0.9600
N1—C21	1.357 (5)	C14—H14B	0.9600
N1—H1A	0.8600	C14—H14C	0.9600
N1—H1B	0.8600	C15—C16	1.456 (5)
C1—C2	1.500 (5)	C16—C17	1.404 (5)
C1—H1C	0.9800	C16—C21	1.410 (5)
C2—C3	1.515 (5)	C17—C18	1.368 (6)
C2—H2A	0.9800	C17—H17A	0.9300
C3—C4	1.522 (5)	C18—C19	1.388 (7)
C3—H3A	0.9800	C18—H18A	0.9300
C4—C5	1.530 (4)	C19—C20	1.342 (7)
C4—H4A	0.9800	C19—H19A	0.9300
C5—C6	1.497 (5)	C20—C21	1.403 (6)
C5—H5A	0.9800	C20—H20A	0.9300
C1—O1—C5	112.2 (2)	H10B—C10—H10C	109.5
C7—O2—C6	115.5 (3)	O7'—C11—O7	39.0 (6)
C9—O4—C4	118.9 (3)	O7'—C11—O6	119.0 (6)
C11—O6—C3	120.2 (3)	O7—C11—O6	119.4 (6)
C13—O8—C2	117.4 (4)	O7'—C11—C12	124.0 (7)
C15—O10—C1	117.7 (3)	O7—C11—C12	123.8 (6)
C21—N1—H1A	120.0	O6—C11—C12	112.6 (4)
C21—N1—H1B	120.0	C11—C12—H12A	109.5
H1A—N1—H1B	120.0	C11—C12—H12B	109.5
O1—C1—O10	106.7 (3)	H12A—C12—H12B	109.5
O1—C1—C2	109.6 (3)	C11—C12—H12C	109.5
O10—C1—C2	107.4 (3)	H12A—C12—H12C	109.5
O1—C1—H1C	111.0	H12B—C12—H12C	109.5
O10—C1—H1C	111.0	C11—C12—H12D	109.5
C2—C1—H1C	111.0	H12A—C12—H12D	141.1
O8—C2—C1	107.6 (3)	H12B—C12—H12D	56.3
O8—C2—C3	108.0 (3)	H12C—C12—H12D	56.3
C1—C2—C3	110.1 (3)	C11—C12—H12E	109.5
O8—C2—H2A	110.3	H12A—C12—H12E	56.3
C1—C2—H2A	110.3	H12B—C12—H12E	141.1
C3—C2—H2A	110.3	H12C—C12—H12E	56.3
O6—C3—C2	107.8 (3)	H12D—C12—H12E	109.5
O6—C3—C4	108.3 (3)	C11—C12—H12F	109.5
C2—C3—C4	111.6 (3)	H12A—C12—H12F	56.3
O6—C3—H3A	109.7	H12B—C12—H12F	56.3
C2—C3—H3A	109.7	H12C—C12—H12F	141.1
C4—C3—H3A	109.7	H12D—C12—H12F	109.5
O4—C4—C3	108.6 (3)	H12E—C12—H12F	109.5
O4—C4—C5	105.5 (2)	O9'—C13—O9	28 (2)
C3—C4—C5	112.4 (3)	O9'—C13—O8	128.1 (11)
O4—C4—H4A	110.1	O9—C13—O8	117.2 (13)
C3—C4—H4A	110.1	O9'—C13—C14	120.6 (12)
C5—C4—H4A	110.1	O9—C13—C14	131.9 (12)
O1—C5—C6	107.8 (3)	O8—C13—C14	109.1 (7)
O1—C5—C4	110.3 (2)	C13—C14—H14A	109.5
C6—C5—C4	109.7 (3)	C13—C14—H14B	109.5
O1—C5—H5A	109.7	H14A—C14—H14B	109.5
C6—C5—H5A	109.7	C13—C14—H14C	109.5
C4—C5—H5A	109.7	H14A—C14—H14C	109.5
O2—C6—C5	108.5 (3)	H14B—C14—H14C	109.5
O2—C6—H6A	110.0	O11—C15—O10	120.9 (3)
C5—C6—H6A	110.0	O11—C15—C16	126.9 (3)
O2—C6—H6B	110.0	O10—C15—C16	112.2 (3)
C5—C6—H6B	110.0	C17—C16—C21	118.7 (3)
H6A—C6—H6B	108.4	C17—C16—C15	120.6 (3)
O3—C7—O2	123.0 (4)	C21—C16—C15	120.7 (3)
O3—C7—C8	124.4 (4)	C18—C17—C16	121.6 (4)
O2—C7—C8	112.5 (4)	C18—C17—H17A	119.2
C7—C8—H8A	109.5	C16—C17—H17A	119.2
C7—C8—H8B	109.5	C17—C18—C19	119.3 (4)
H8A—C8—H8B	109.5	C17—C18—H18A	120.4
C7—C8—H8C	109.5	C19—C18—H18A	120.4
H8A—C8—H8C	109.5	C20—C19—C18	120.2 (4)
H8B—C8—H8C	109.5	C20—C19—H19A	119.9
O5—C9—O4	122.9 (3)	C18—C19—H19A	119.9
O5—C9—C10	126.6 (4)	C19—C20—C21	122.7 (4)
O4—C9—C10	110.5 (3)	C19—C20—H20A	118.6
C9—C10—H10A	109.5	C21—C20—H20A	118.6
C9—C10—H10B	109.5	N1—C21—C20	120.4 (4)
H10A—C10—H10B	109.5	N1—C21—C16	122.1 (4)
C9—C10—H10C	109.5	C20—C21—C16	117.5 (4)
H10A—C10—H10C	109.5
C5—O1—C1—O10	177.4 (2)	O1—C5—C6—O2	72.2 (3)
C5—O1—C1—C2	−66.6 (3)	C4—C5—C6—O2	−167.7 (3)
C15—O10—C1—O1	−84.7 (3)	C6—O2—C7—O3	−7.3 (6)
C15—O10—C1—C2	157.9 (3)	C6—O2—C7—C8	174.2 (4)
C13—O8—C2—C1	109.3 (4)	C4—O4—C9—O5	−1.8 (5)
C13—O8—C2—C3	−131.8 (4)	C4—O4—C9—C10	−180.0 (3)
O1—C1—C2—O8	177.5 (3)	C3—O6—C11—O7'	−21.7 (9)
O10—C1—C2—O8	−67.0 (3)	C3—O6—C11—O7	23.3 (8)
O1—C1—C2—C3	60.0 (3)	C3—O6—C11—C12	−179.0 (3)
O10—C1—C2—C3	175.5 (3)	C2—O8—C13—O9'	−7.0 (19)
C11—O6—C3—C2	−124.0 (3)	C2—O8—C13—O9	23.4 (19)
C11—O6—C3—C4	115.1 (4)	C2—O8—C13—C14	−170.0 (4)
O8—C2—C3—O6	73.9 (3)	C1—O10—C15—O11	−1.9 (5)
C1—C2—C3—O6	−168.8 (3)	C1—O10—C15—C16	177.2 (3)
O8—C2—C3—C4	−167.2 (3)	O11—C15—C16—C17	−175.7 (4)
C1—C2—C3—C4	−49.9 (4)	O10—C15—C16—C17	5.2 (5)
C9—O4—C4—C3	101.4 (3)	O11—C15—C16—C21	2.4 (6)
C9—O4—C4—C5	−137.9 (3)	O10—C15—C16—C21	−176.7 (3)
O6—C3—C4—O4	−79.8 (3)	C21—C16—C17—C18	1.2 (6)
C2—C3—C4—O4	161.6 (2)	C15—C16—C17—C18	179.3 (4)
O6—C3—C4—C5	163.8 (2)	C16—C17—C18—C19	−0.8 (7)
C2—C3—C4—C5	45.2 (3)	C17—C18—C19—C20	0.0 (8)
C1—O1—C5—C6	−179.8 (3)	C18—C19—C20—C21	0.3 (8)
C1—O1—C5—C4	60.5 (3)	C19—C20—C21—N1	178.9 (4)
O4—C4—C5—O1	−167.3 (2)	C19—C20—C21—C16	0.1 (7)
C3—C4—C5—O1	−49.1 (3)	C17—C16—C21—N1	−179.6 (4)
O4—C4—C5—C6	74.1 (3)	C15—C16—C21—N1	2.2 (6)
C3—C4—C5—C6	−167.7 (3)	C17—C16—C21—C20	−0.8 (5)
C7—O2—C6—C5	169.0 (3)	C15—C16—C21—C20	−178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O11	0.86	2.06	2.704 (5)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O11	0.86	2.06	2.704 (5)	131