trans-4-Nitro­phenyl 4-(tosyl­oxymeth­yl)cyclo­hexa­necarboxyl­ate

Qi, Q.-R.; Huang, W.-C.; Mao, Z.-H.; Zheng, H.

doi:10.1107/S1600536808000068

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o385

doi:10.1107/S1600536808000068

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trans-4-Nitrophenyl 4-(tosyloxymethyl)cyclohexanecarboxylate

Qing-Rong Qi,^a Wen-Cai Huang,^b Zhi-Hua Mao ^c and Hu Zheng ^a ^*

^aDepartment of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China, ^bDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China, and ^cThe Center for Testing and Analysis, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: wcums416@yahoo.com.cn

(Received 18 December 2007; accepted 2 January 2008; online 9 January 2008)

The title compound, C₂₁H₂₃NO₇S, is an important intermediate in the synthesis of poly(amidoamine) dendrimers. The cyclohexane ring adopts a chair conformation. The dihedral angle between the two aromatic rings is 69.5 (2)°. The molecules are linked into a zigzag chain along the b axis by C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Bucourt & Hainaut (1965 ); Dunitz & Strickler (1966 ); Sewald & Jakubke (2002 ); Luger et al. (1972 ); van Koningsveld & Jansen (1984 ).

Experimental

Crystal data

C₂₁H₂₃NO₇S
M_r = 433.46
Monoclinic, P 2₁ /c
a = 20.499 (5) Å
b = 6.111 (3) Å
c = 17.250 (4) Å
β = 102.04 (3)°
V = 2113.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 292 (2) K
0.40 × 0.38 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
4094 measured reflections
3627 independent reflections
1850 reflections with I > 2σ(I)
R_int = 0.004
3 standard reflections every 300 reflections intensity decay: 2.1%

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.191
S = 1.06
3627 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O7ⁱ	0.93	2.49	3.290 (6)	144
Symmetry code: (i) $[-x, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000068/ci2549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000068/ci2549Isup2.hkl

checkCIF report

Comment top

Activated esters are commonly used in peptide synthesis to facilitate the reaction of carboxylic acid and amine to obtain amide. trans-Nitrophenyl ester of N-protected amino acid can react with amino group quickly at room temperature with fairly good yields (Sewald et al.,2002). In our work, cyclohexane derivatives were designed to be linked to poly(amidoamine)dendrimer[PAMAM] through the amide bond which could be formed by the reaction of terminal amino groups of PAMAM dendrimer and cyclohexanecarboxylic acid. So the title compound, a p-nitrophenyl ester of trans-4-(tosyloxymethyl) cyclohexanecarboxylic acid was synthesized. As expected, the modification of periphery of PAMAM dendrimer effectively is realised under mild conditions. We report here the crystal structure of the title compound.

The cyclohexane ring of the title compound adopts a chair conformation. The average C—C bond length of the cyclohexane ring is 1.521 (5) Å, which is close to that of trans-1,4-cyclohexanedicarboxylic acid (1.523 (3) Å, Von Luger et al., 1972). The mean endocyclic angle of the cyclohexane is 111.08 (3)°, which is close to that observed for cyclohexane rings (111.1°, Bucourt & Hainaut, 1965; 111.4 (4)°, Dunitz & Strickler, 1966; Von Luger et al., 1972).

The molecules are linked into a zigzag chain along the b axis by C—H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Bucourt & Hainaut (1965); Dunitz & Strickler (1966); Sewald & Jakubke (2002); Luger et al. (1972); van Koningsveld & Jansen (1984).

Experimental top

trans-4-(Tosyloxymethyl)cyclohexanecarboxylic acid (10 mmol) and p-nitrophenol (11 mmol) were dissolved in ethyl acetate (10 ml) and the solution was cooled to 273 K in an ice bath. Then a solution of DCC (11 mmol) in ethyl acetate (5 ml) was added dropwsie with stirring. After the addition, the stirring was continued for 30 min at 273 K and for 24 h at room temperature. Then acetic acid (0.5 ml) was added and after 30 min the reaction solution was filtered and the filtrate was evaporated to leave a yellow solid. The title compound was recrystallized from acetone. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a acetone-water solution at room temperature.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids drawn at the 30% probability level.

trans-4-Nitrophenyl 4-(tosyloxymethyl)cyclohexanecarboxylate top

Crystal data top

C₂₁H₂₃NO₇S	F(000) = 912
M_r = 433.46	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33 reflections
a = 20.499 (5) Å	θ = 4.5–7.6°
b = 6.111 (3) Å	µ = 0.20 mm⁻¹
c = 17.250 (4) Å	T = 292 K
β = 102.04 (3)°	Block, colourless
V = 2113.4 (13) Å³	0.40 × 0.38 × 0.30 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.004
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.0°
Graphite monochromator	h = −8→24
ω/2θ scans	k = −7→0
4094 measured reflections	l = −20→19
3627 independent reflections	3 standard reflections every 300 reflections
1850 reflections with I > 2σ(I)	intensity decay: 2.1%

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.097P)²] where P = (F_o² + 2F_c²)/3
3627 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₂₁H₂₃NO₇S	V = 2113.4 (13) Å³
M_r = 433.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.499 (5) Å	µ = 0.20 mm⁻¹
b = 6.111 (3) Å	T = 292 K
c = 17.250 (4) Å	0.40 × 0.38 × 0.30 mm
β = 102.04 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.004
4094 measured reflections	3 standard reflections every 300 reflections
3627 independent reflections	intensity decay: 2.1%
1850 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
3627 reflections	Δρ_min = −0.53 e Å⁻³
272 parameters

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	0.30112 (5)	−0.15510 (18)	0.17299 (7)	0.0556 (4)
O1	0.30040 (14)	−0.0770 (6)	0.09454 (16)	0.0702 (9)
O2	0.30099 (14)	−0.3830 (5)	0.1871 (2)	0.0763 (10)
O3	0.23652 (12)	−0.0742 (5)	0.19982 (18)	0.0632 (8)
O4	−0.09447 (15)	0.2718 (6)	0.1532 (2)	0.0885 (12)
O5	−0.08914 (13)	0.5252 (5)	0.06303 (18)	0.0686 (9)
O6	−0.39478 (15)	0.7233 (6)	−0.0126 (2)	0.0813 (11)
O7	−0.36075 (17)	0.9887 (7)	0.0674 (2)	0.0936 (12)
N1	−0.35100 (18)	0.8235 (8)	0.0323 (2)	0.0635 (10)
C1	0.39156 (18)	0.1686 (7)	0.2212 (2)	0.0500 (10)
H1	0.3740	0.2367	0.1732	0.060*
C2	0.44258 (19)	0.2665 (7)	0.2753 (2)	0.0536 (11)
H2	0.4589	0.4016	0.2633	0.064*
C3	0.46966 (18)	0.1673 (8)	0.3465 (2)	0.0526 (10)
C4	0.4444 (2)	−0.0304 (9)	0.3636 (3)	0.0650 (13)
H4	0.4618	−0.0973	0.4119	0.078*
C5	0.3931 (2)	−0.1337 (8)	0.3100 (2)	0.0593 (12)
H5	0.3769	−0.2690	0.3220	0.071*
C6	0.36691 (17)	−0.0320 (6)	0.2393 (2)	0.0440 (9)
C7	0.5248 (2)	0.2787 (10)	0.4050 (3)	0.0811 (16)
H7A	0.5125	0.4279	0.4121	0.122*
H7B	0.5652	0.2753	0.3852	0.122*
H7C	0.5316	0.2037	0.4550	0.122*
C8	0.21871 (19)	0.1584 (7)	0.1883 (3)	0.0657 (12)
H8A	0.2286	0.2104	0.1389	0.079*
H8B	0.2442	0.2448	0.2313	0.079*
C9	0.14546 (17)	0.1807 (7)	0.1864 (2)	0.0507 (10)
H9	0.1370	0.1230	0.2364	0.061*
C10	0.10207 (18)	0.0551 (7)	0.1192 (2)	0.0527 (10)
H10A	0.1131	−0.0992	0.1249	0.063*
H10B	0.1115	0.1046	0.0692	0.063*
C11	0.02817 (18)	0.0850 (8)	0.1176 (2)	0.0564 (11)
H11A	0.0178	0.0238	0.1655	0.068*
H11B	0.0023	0.0067	0.0726	0.068*
C12	0.00917 (18)	0.3266 (7)	0.1115 (2)	0.0525 (11)
H12	0.0175	0.3836	0.0614	0.063*
C13	0.05248 (19)	0.4533 (7)	0.1792 (3)	0.0614 (12)
H13A	0.0426	0.4050	0.2291	0.074*
H13B	0.0418	0.6078	0.1732	0.074*
C14	0.1265 (2)	0.4210 (7)	0.1814 (3)	0.0648 (12)
H14A	0.1374	0.4839	0.1340	0.078*
H14B	0.1523	0.4975	0.2269	0.078*
C15	−0.0628 (2)	0.3620 (8)	0.1128 (2)	0.0545 (11)
C16	−0.1560 (2)	0.5894 (8)	0.0600 (2)	0.0574 (12)
C17	−0.2075 (2)	0.4605 (8)	0.0214 (3)	0.0662 (13)
H17	−0.1994	0.3249	0.0008	0.079*
C18	−0.2720 (2)	0.5386 (8)	0.0140 (3)	0.0631 (13)
H18	−0.3080	0.4554	−0.0120	0.076*
C19	−0.28246 (19)	0.7380 (8)	0.0449 (2)	0.0509 (10)
C20	−0.2310 (2)	0.8667 (8)	0.0847 (2)	0.0623 (12)
H20	−0.2392	1.0013	0.1059	0.075*
C21	−0.1658 (2)	0.7874 (9)	0.0920 (3)	0.0665 (13)
H21	−0.1297	0.8690	0.1185	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0444 (6)	0.0441 (7)	0.0734 (8)	0.0019 (5)	0.0014 (5)	−0.0017 (6)
O1	0.068 (2)	0.082 (2)	0.0556 (18)	0.0010 (16)	0.0017 (14)	−0.0056 (17)
O2	0.0633 (19)	0.041 (2)	0.114 (3)	−0.0006 (15)	−0.0060 (17)	0.0007 (19)
O3	0.0386 (15)	0.053 (2)	0.096 (2)	0.0042 (13)	0.0114 (14)	0.0135 (17)
O4	0.0562 (19)	0.106 (3)	0.108 (3)	0.0247 (18)	0.0286 (18)	0.052 (2)
O5	0.0447 (16)	0.079 (2)	0.082 (2)	0.0155 (15)	0.0136 (14)	0.0340 (19)
O6	0.0471 (18)	0.101 (3)	0.091 (2)	0.0097 (18)	0.0021 (17)	−0.007 (2)
O7	0.082 (2)	0.105 (3)	0.095 (3)	0.027 (2)	0.0196 (19)	−0.024 (3)
N1	0.060 (2)	0.073 (3)	0.059 (2)	0.018 (2)	0.0138 (19)	0.000 (2)
C1	0.050 (2)	0.047 (3)	0.054 (2)	0.0062 (19)	0.0105 (18)	0.002 (2)
C2	0.052 (2)	0.047 (3)	0.062 (3)	−0.0082 (19)	0.012 (2)	0.003 (2)
C3	0.043 (2)	0.063 (3)	0.054 (2)	−0.004 (2)	0.0146 (18)	−0.001 (2)
C4	0.064 (3)	0.078 (4)	0.050 (2)	−0.004 (2)	0.006 (2)	0.011 (2)
C5	0.061 (3)	0.057 (3)	0.062 (3)	−0.006 (2)	0.016 (2)	0.009 (2)
C6	0.043 (2)	0.034 (2)	0.056 (2)	0.0020 (16)	0.0105 (17)	0.0054 (19)
C7	0.063 (3)	0.106 (5)	0.070 (3)	−0.017 (3)	0.003 (2)	−0.013 (3)
C8	0.043 (2)	0.045 (3)	0.109 (4)	0.0012 (19)	0.015 (2)	0.001 (3)
C9	0.041 (2)	0.047 (3)	0.064 (3)	0.0016 (17)	0.0104 (18)	0.005 (2)
C10	0.050 (2)	0.041 (3)	0.068 (3)	0.0056 (18)	0.0142 (19)	−0.006 (2)
C11	0.047 (2)	0.059 (3)	0.061 (3)	−0.0058 (19)	0.0077 (19)	−0.011 (2)
C12	0.042 (2)	0.063 (3)	0.053 (2)	0.008 (2)	0.0124 (17)	0.010 (2)
C13	0.048 (2)	0.042 (3)	0.095 (3)	0.0063 (19)	0.016 (2)	−0.008 (2)
C14	0.050 (2)	0.046 (3)	0.098 (3)	−0.004 (2)	0.013 (2)	−0.006 (3)
C15	0.050 (2)	0.056 (3)	0.057 (2)	0.006 (2)	0.010 (2)	0.012 (2)
C16	0.047 (2)	0.067 (3)	0.057 (3)	0.008 (2)	0.0088 (19)	0.019 (2)
C17	0.059 (3)	0.056 (3)	0.079 (3)	0.014 (2)	0.005 (2)	−0.014 (3)
C18	0.045 (2)	0.071 (4)	0.067 (3)	−0.001 (2)	−0.001 (2)	−0.004 (3)
C19	0.048 (2)	0.054 (3)	0.049 (2)	0.005 (2)	0.0060 (18)	0.001 (2)
C20	0.062 (3)	0.059 (3)	0.063 (3)	0.007 (2)	0.007 (2)	−0.004 (2)
C21	0.056 (3)	0.069 (4)	0.068 (3)	−0.005 (2)	−0.003 (2)	0.000 (3)

Geometric parameters (Å, º) top

S1—O2	1.414 (3)	C9—C10	1.515 (5)
S1—O1	1.432 (3)	C9—C14	1.517 (6)
S1—O3	1.571 (3)	C9—H9	0.98
S1—C6	1.747 (4)	C10—C11	1.520 (5)
O3—C8	1.471 (5)	C10—H10A	0.97
O4—C15	1.184 (5)	C10—H10B	0.97
O5—C15	1.353 (5)	C11—C12	1.525 (6)
O5—C16	1.416 (5)	C11—H11A	0.97
O6—N1	1.221 (5)	C11—H11B	0.97
O7—N1	1.214 (5)	C12—C15	1.495 (5)
N1—C19	1.472 (5)	C12—C13	1.523 (6)
C1—C2	1.383 (5)	C12—H12	0.98
C1—C6	1.386 (6)	C13—C14	1.523 (5)
C1—H1	0.93	C13—H13A	0.97
C2—C3	1.379 (6)	C13—H13B	0.97
C2—H2	0.93	C14—H14A	0.97
C3—C4	1.371 (6)	C14—H14B	0.97
C3—C7	1.511 (6)	C16—C21	1.362 (6)
C4—C5	1.399 (6)	C16—C17	1.374 (6)
C4—H4	0.93	C17—C18	1.386 (6)
C5—C6	1.373 (5)	C17—H17	0.93
C5—H5	0.93	C18—C19	1.365 (6)
C7—H7A	0.96	C18—H18	0.93
C7—H7B	0.96	C19—C20	1.379 (6)
C7—H7C	0.96	C20—C21	1.402 (6)
C8—C9	1.501 (5)	C20—H20	0.93
C8—H8A	0.97	C21—H21	0.93
C8—H8B	0.97

O2—S1—O1	119.4 (2)	C11—C10—H10A	109.2
O2—S1—O3	103.13 (18)	C9—C10—H10B	109.2
O1—S1—O3	109.29 (18)	C11—C10—H10B	109.2
O2—S1—C6	109.87 (18)	H10A—C10—H10B	107.9
O1—S1—C6	109.28 (19)	C10—C11—C12	110.9 (3)
O3—S1—C6	104.74 (18)	C10—C11—H11A	109.5
C8—O3—S1	117.7 (3)	C12—C11—H11A	109.5
C15—O5—C16	118.9 (3)	C10—C11—H11B	109.5
O7—N1—O6	123.9 (4)	C12—C11—H11B	109.5
O7—N1—C19	118.2 (4)	H11A—C11—H11B	108.0
O6—N1—C19	117.9 (4)	C15—C12—C13	109.5 (3)
C2—C1—C6	119.4 (4)	C15—C12—C11	112.2 (4)
C2—C1—H1	120.3	C13—C12—C11	109.9 (3)
C6—C1—H1	120.3	C15—C12—H12	108.4
C3—C2—C1	121.2 (4)	C13—C12—H12	108.4
C3—C2—H2	119.4	C11—C12—H12	108.4
C1—C2—H2	119.4	C12—C13—C14	111.8 (4)
C4—C3—C2	118.6 (4)	C12—C13—H13A	109.3
C4—C3—C7	121.1 (4)	C14—C13—H13A	109.3
C2—C3—C7	120.2 (4)	C12—C13—H13B	109.3
C3—C4—C5	121.4 (4)	C14—C13—H13B	109.3
C3—C4—H4	119.3	H13A—C13—H13B	107.9
C5—C4—H4	119.3	C9—C14—C13	111.6 (3)
C6—C5—C4	118.9 (4)	C9—C14—H14A	109.3
C6—C5—H5	120.5	C13—C14—H14A	109.3
C4—C5—H5	120.5	C9—C14—H14B	109.3
C5—C6—C1	120.4 (4)	C13—C14—H14B	109.3
C5—C6—S1	119.5 (3)	H14A—C14—H14B	108.0
C1—C6—S1	120.1 (3)	O4—C15—O5	121.4 (4)
C3—C7—H7A	109.5	O4—C15—C12	127.3 (4)
C3—C7—H7B	109.5	O5—C15—C12	111.2 (4)
H7A—C7—H7B	109.5	C21—C16—C17	122.9 (4)
C3—C7—H7C	109.5	C21—C16—O5	117.0 (4)
H7A—C7—H7C	109.5	C17—C16—O5	120.0 (4)
H7B—C7—H7C	109.5	C16—C17—C18	118.0 (5)
O3—C8—C9	108.0 (3)	C16—C17—H17	121.0
O3—C8—H8A	110.1	C18—C17—H17	121.0
C9—C8—H8A	110.1	C19—C18—C17	119.7 (4)
O3—C8—H8B	110.1	C19—C18—H18	120.1
C9—C8—H8B	110.1	C17—C18—H18	120.1
H8A—C8—H8B	108.4	C18—C19—C20	122.6 (4)
C8—C9—C10	113.3 (4)	C18—C19—N1	118.8 (4)
C8—C9—C14	109.4 (3)	C20—C19—N1	118.6 (4)
C10—C9—C14	110.1 (3)	C19—C20—C21	117.6 (5)
C8—C9—H9	107.9	C19—C20—H20	121.2
C10—C9—H9	107.9	C21—C20—H20	121.2
C14—C9—H9	107.9	C16—C21—C20	119.3 (4)
C9—C10—C11	112.2 (3)	C16—C21—H21	120.4
C9—C10—H10A	109.2	C20—C21—H21	120.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O7ⁱ	0.93	2.49	3.290 (6)	144

Symmetry code: (i) −x, y−3/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₇S
M_r	433.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	20.499 (5), 6.111 (3), 17.250 (4)
β (°)	102.04 (3)
V (Å³)	2113.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.40 × 0.38 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4094, 3627, 1850
R_int	0.004
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.191, 1.06
No. of reflections	3627
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.53

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O7ⁱ	0.93	2.49	3.290 (6)	144

Symmetry code: (i) −x, y−3/2, −z+1/2.

References

Bucourt, R. & Hainaut, D. (1965). Bull. Soc. Chim. Fr. 5, 1366–1378. Google Scholar
Dunitz, J. D. & Strickler, P. (1966). Helv. Chim. Acta, 49, 290–291. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Meeting, Pittsburgh, Abstract PA 104. Google Scholar
Koningsveld, H. van & Jansen, J. C. (1984). Acta Cryst. B40, 420–424. CSD CrossRef Web of Science IUCr Journals Google Scholar
Luger, P., Plieth, K. & Ruban, G. (1972). Acta Cryst. B28, 706–710. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sewald, N. & Jakubke, H. D. (2002). Peptides: Chemistry and Biology, 1st ed. Weinheim: Wiley. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 2| February 2008| Page o385

doi:10.1107/S1600536808000068

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