Ethyl 2-(N-cyclo­hexyl-2-nitro­phenyl­sulfonamido)-2-oxoacetate

Wang, B.-L.; He, F.-Q.; Li, Z.-M.; Song, H.-B.

doi:10.1107/S1600536807026785

Buy article online - an online subscription or single-article purchase is required to access this article.

Ethyl 2-(N-cyclohexyl-2-nitrophenylsulfonamido)-2-oxoacetate

B.-L. Wang, F.-Q. He, Z.-M. Li and H.-B. Song

In the title compound, C₁₆H₂₀N₂O₇S, the cyclohexane ring has a chair conformation and the two C=O groups are in a trans arrangement, the O=C-C=O torsion angle being -114.0 (5)°. The dihedral angle between the tertiary amine plane and the ethoxycarbonyl group O-C=O is 75.1 (2)°, while the dihedral angle between the amine plane and the benzene ring is 74.0 (2)°.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026785/bh2108sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026785/bh2108Isup2.hkl Contains datablock I

CCDC reference: 655602

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.128
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.08 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O3      ..       5.29 su
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Inhibitors of KARI (ketol-acid reductoisomerase) have been synthesized and tested as herbicides. 2-Dimethylphosphinoyl-2-hydroxy acetic acid (Hoe 704, Schulz et al., 1988), N-hydroxy-N-isopropyloxamate (IpOHA, Aulabaugh et al., 1990) and cyclopropane-1,1-dicarboxylate (CPD, Lee et al., 2005) are potent inhibitors of the enzyme in vitro but their activity as herbicides are weak. There are few reports about the design, synthesis and biological activity of new KARI inhibitors. Nevertheless, inhibitors of KARI remain a potential source for finding novel herbicidal compounds (Wang et al., 2005). With this in mind, a series of ethyl-2-(N-substituted-arylsulfonamido)-2-oxoacetate compounds has been designed and synthesized, based on the structure of KARI inhibitor IpOHA. The X-ray crystal structure determination of the title compound, (I), was undertaken in order to investigate the relationship between structure and herbicidal activity.

The X-ray analysis reveals that in the title compound, the cyclohexane ring is in a chair conformation and is bonded to the amine N atom (Fig. 1). Two C═ O groups are trans arranged, with the torsion angle O5—C13—C14—O6 being -114.0 (5)°. The dihedral angle between the tertiary amine plane (S1/C7/C13/N2) and ethoxylcarbonyl O—C═O group (O6/O7/O14) is 75.1 (2)°. The dihedral angle between the amine plane and benzene ring C1···C6 is 74.0 (2)°.

Related literature top

For related reports, see: Schulz et al. (1988); Aulabaugh & Schloss (1990); Lee et al. (2005); Wang et al. (2005).

Experimental top

To a well stirred solution of N-cyclohexyl-2-nitrobenzenesulfonamide (5.68 g, 0.02 mol) in 20 ml of dry THF was added 50% NaH (1.44 g, 0.03 mol) slowly. After 1 h under stirring, a solution of ethyl oxalyl chloride (2.73 g, 0.02 mol) in 5 ml of dry THF was dropwise added and the mixture further stirred at 313–323 K for 3 h. After removing the solvent, water was added (20 ml), and the mixture was extracted with ethyl acetate and dried over magnesium sulfate. The ester was removed and the residue was purified by chromatography over silica gel with petroleum ether/ethyl acetate as eluent (9:1), affording (I). Yield: 87%; m.p. 391–392 K. ¹H NMR (CDCl₃) δ: 8.34–7.75 (m, 4H, Ph—H), 4.36 (q, J=7.20 Hz, 2H, CH₂), 3.88–3.78 (m, 1H, cyclohexyl-CH), 1.37 (t, J=7.20 Hz, 3H, CH₃), 2.23–1.11 (m, 10H, cyclohexyl-CH₂). Anal. Calcd. for C₁₆H₂₀N₂O₇S: C 49.99, H 5.24, N 7.29%. Found: C 50.13, H 5.31, N 7.61%. Colourless single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from petroleum ether and ethyl acetate (1:1).

Structure description top

For related reports, see: Schulz et al. (1988); Aulabaugh & Schloss (1990); Lee et al. (2005); Wang et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 20% probability level.

Ethyl 2-(N-cyclohexyl-2-nitrophenylsulfonamido)-2-oxoacetate top

Crystal data top

C₁₆H₂₀N₂O₇S	F(000) = 808
M_r = 384.40	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 391–392 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.962 (7) Å	Cell parameters from 1731 reflections
b = 12.352 (7) Å	θ = 2.2–21.7°
c = 13.879 (8) Å	µ = 0.22 mm⁻¹
β = 101.813 (11)°	T = 294 K
V = 1839.5 (19) Å³	Block, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3240 independent reflections
Radiation source: fine-focus sealed tube	1813 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→11
T_min = 0.896, T_max = 0.960	k = −14→12
9177 measured reflections	l = −16→16

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0538P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3240 reflections	Δρ_max = 0.23 e Å⁻³
237 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (2)

Crystal data top

C₁₆H₂₀N₂O₇S	V = 1839.5 (19) Å³
M_r = 384.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.962 (7) Å	µ = 0.22 mm⁻¹
b = 12.352 (7) Å	T = 294 K
c = 13.879 (8) Å	0.24 × 0.22 × 0.20 mm
β = 101.813 (11)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3240 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1813 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.960	R_int = 0.074
9177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
3240 reflections	Δρ_min = −0.26 e Å⁻³
237 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.30775 (8)	0.54366 (6)	0.13647 (6)	0.0434 (3)
O1	−0.0287 (3)	0.6633 (2)	0.0056 (2)	0.0895 (10)
O2	0.1287 (3)	0.7293 (2)	0.10732 (18)	0.0711 (8)
O3	0.2700 (2)	0.56089 (16)	0.03315 (15)	0.0525 (6)
O4	0.3794 (2)	0.62380 (16)	0.19704 (17)	0.0578 (7)
O5	0.5814 (3)	0.3564 (2)	0.2134 (2)	0.1016 (11)
O6	0.4471 (3)	0.4822 (2)	0.36867 (19)	0.0739 (8)
O7	0.6185 (2)	0.55085 (19)	0.32483 (16)	0.0622 (7)
N1	0.0524 (3)	0.6590 (2)	0.0797 (2)	0.0554 (8)
N2	0.3898 (2)	0.42994 (18)	0.15192 (18)	0.0429 (7)
C1	0.0573 (3)	0.5618 (2)	0.1426 (2)	0.0444 (8)
C2	−0.0531 (3)	0.5281 (3)	0.1653 (3)	0.0630 (10)
H2	−0.1273	0.5634	0.1389	0.076*
C3	−0.0524 (4)	0.4413 (3)	0.2278 (3)	0.0704 (11)
H3	−0.1263	0.4173	0.2438	0.085*
C4	0.0586 (4)	0.3903 (3)	0.2665 (3)	0.0645 (11)
H4	0.0592	0.3324	0.3094	0.077*
C5	0.1687 (3)	0.4233 (2)	0.2427 (2)	0.0494 (9)
H5	0.2425	0.3874	0.2694	0.059*
C6	0.1703 (3)	0.5101 (2)	0.1792 (2)	0.0396 (8)
C7	0.3473 (3)	0.3418 (2)	0.0781 (2)	0.0423 (8)
H7	0.2593	0.3564	0.0502	0.051*
C8	0.4136 (3)	0.3436 (3)	−0.0075 (2)	0.0556 (10)
H8A	0.5012	0.3272	0.0158	0.067*
H8B	0.4072	0.4152	−0.0368	0.067*
C9	0.3552 (3)	0.2602 (3)	−0.0844 (2)	0.0618 (11)
H9A	0.2698	0.2809	−0.1121	0.074*
H9B	0.4008	0.2591	−0.1374	0.074*
C10	0.3567 (4)	0.1474 (3)	−0.0398 (3)	0.0631 (11)
H10A	0.3144	0.0972	−0.0892	0.076*
H10B	0.4422	0.1232	−0.0186	0.076*
C11	0.2935 (4)	0.1475 (3)	0.0467 (3)	0.0668 (11)
H11A	0.2993	0.0757	0.0757	0.080*
H11B	0.2059	0.1644	0.0241	0.080*
C12	0.3517 (4)	0.2296 (3)	0.1251 (2)	0.0613 (10)
H12A	0.4374	0.2097	0.1524	0.074*
H12B	0.3061	0.2302	0.1780	0.074*
C13	0.5018 (4)	0.4223 (3)	0.2206 (3)	0.0598 (10)
C14	0.5169 (4)	0.4910 (3)	0.3133 (3)	0.0539 (9)
C15	0.6404 (4)	0.6210 (3)	0.4111 (3)	0.0705 (11)
H15A	0.6423	0.5787	0.4702	0.085*
H15B	0.5742	0.6743	0.4057	0.085*
C16	0.7611 (4)	0.6753 (4)	0.4156 (4)	0.1046 (16)
H16A	0.8246	0.6219	0.4152	0.157*
H16B	0.7816	0.7173	0.4749	0.157*
H16C	0.7557	0.7221	0.3597	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0479 (5)	0.0345 (5)	0.0484 (5)	−0.0014 (4)	0.0111 (4)	−0.0009 (4)
O1	0.068 (2)	0.105 (2)	0.083 (2)	0.0049 (16)	−0.0142 (17)	0.0407 (17)
O2	0.099 (2)	0.0392 (15)	0.0726 (18)	−0.0055 (15)	0.0123 (16)	0.0008 (13)
O3	0.0659 (16)	0.0518 (14)	0.0419 (13)	0.0043 (11)	0.0156 (11)	0.0094 (11)
O4	0.0561 (16)	0.0374 (13)	0.0761 (16)	−0.0097 (11)	0.0047 (13)	−0.0102 (12)
O5	0.070 (2)	0.104 (2)	0.112 (2)	0.0413 (18)	−0.0251 (17)	−0.0567 (19)
O6	0.082 (2)	0.0768 (19)	0.0632 (17)	−0.0175 (15)	0.0156 (16)	−0.0083 (14)
O7	0.0566 (16)	0.0690 (17)	0.0578 (15)	−0.0069 (13)	0.0042 (12)	−0.0229 (13)
N1	0.056 (2)	0.050 (2)	0.059 (2)	0.0125 (16)	0.0109 (17)	0.0091 (16)
N2	0.0451 (17)	0.0363 (15)	0.0455 (16)	0.0027 (12)	0.0050 (13)	−0.0092 (12)
C1	0.050 (2)	0.042 (2)	0.0414 (19)	0.0009 (17)	0.0101 (16)	0.0018 (15)
C2	0.047 (2)	0.070 (3)	0.073 (3)	0.006 (2)	0.017 (2)	0.003 (2)
C3	0.062 (3)	0.072 (3)	0.084 (3)	−0.008 (2)	0.032 (2)	0.012 (2)
C4	0.075 (3)	0.056 (2)	0.070 (3)	−0.006 (2)	0.032 (2)	0.014 (2)
C5	0.056 (2)	0.039 (2)	0.054 (2)	0.0025 (16)	0.0137 (18)	0.0072 (16)
C6	0.046 (2)	0.0351 (18)	0.0382 (18)	−0.0046 (15)	0.0088 (15)	−0.0032 (14)
C7	0.045 (2)	0.0376 (19)	0.0441 (19)	−0.0018 (15)	0.0078 (16)	−0.0091 (15)
C8	0.059 (2)	0.051 (2)	0.062 (2)	−0.0047 (17)	0.026 (2)	−0.0094 (18)
C9	0.076 (3)	0.061 (2)	0.054 (2)	−0.002 (2)	0.025 (2)	−0.0127 (19)
C10	0.078 (3)	0.051 (2)	0.061 (2)	−0.0043 (19)	0.016 (2)	−0.0168 (19)
C11	0.095 (3)	0.041 (2)	0.067 (3)	−0.007 (2)	0.022 (2)	−0.0048 (19)
C12	0.088 (3)	0.046 (2)	0.050 (2)	0.000 (2)	0.014 (2)	−0.0057 (18)
C13	0.054 (2)	0.054 (2)	0.066 (2)	0.0071 (19)	−0.002 (2)	−0.0185 (19)
C14	0.051 (2)	0.050 (2)	0.055 (2)	0.0026 (19)	−0.005 (2)	−0.0090 (18)
C15	0.072 (3)	0.066 (3)	0.069 (3)	−0.012 (2)	0.003 (2)	−0.027 (2)
C16	0.094 (4)	0.094 (3)	0.125 (4)	−0.035 (3)	0.019 (3)	−0.045 (3)

Geometric parameters (Å, º) top

S1—O3	1.425 (2)	C7—C12	1.528 (4)
S1—O4	1.426 (2)	C7—H7	0.9800
S1—N2	1.658 (3)	C8—C9	1.527 (4)
O5—C13	1.212 (4)	C8—H8A	0.9700
N2—C13	1.395 (4)	C8—H8B	0.9700
N2—C7	1.502 (4)	C9—C10	1.524 (4)
S1—C6	1.778 (3)	C9—H9A	0.9700
O1—N1	1.216 (4)	C9—H9B	0.9700
O2—N1	1.212 (3)	C10—C11	1.504 (5)
O6—C14	1.195 (4)	C10—H10A	0.9700
O7—C14	1.319 (4)	C10—H10B	0.9700
O7—C15	1.458 (4)	C11—C12	1.528 (4)
N1—C1	1.478 (4)	C11—H11A	0.9700
C1—C2	1.377 (5)	C11—H11B	0.9700
C1—C6	1.395 (4)	C12—H12A	0.9700
C2—C3	1.377 (5)	C12—H12B	0.9700
C2—H2	0.9300	C13—C14	1.522 (5)
C3—C4	1.378 (5)	C15—C16	1.473 (5)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.376 (5)	C15—H15B	0.9700
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.390 (4)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C7—C8	1.514 (4)

O3—S1—C6	106.24 (15)	C10—C9—C8	111.4 (3)
O3—S1—O4	120.07 (14)	C10—C9—H9A	109.4
O3—S1—N2	107.14 (13)	C8—C9—H9A	109.4
O4—S1—N2	107.06 (14)	C10—C9—H9B	109.4
O4—S1—C6	111.55 (14)	C8—C9—H9B	109.4
N2—S1—C6	103.50 (14)	H9A—C9—H9B	108.0
C7—N2—S1	116.2 (2)	C11—C10—C9	110.8 (3)
C13—N2—C7	121.6 (2)	C11—C10—H10A	109.5
C13—N2—S1	121.6 (2)	C9—C10—H10A	109.5
C14—O7—C15	115.2 (3)	C11—C10—H10B	109.5
O2—N1—O1	125.0 (3)	C9—C10—H10B	109.5
O2—N1—C1	117.1 (3)	H10A—C10—H10B	108.1
O1—N1—C1	117.8 (3)	C10—C11—C12	112.0 (3)
C2—C1—C6	122.3 (3)	C10—C11—H11A	109.2
C2—C1—N1	117.0 (3)	C12—C11—H11A	109.2
C6—C1—N1	120.6 (3)	C10—C11—H11B	109.2
C1—C2—C3	119.2 (3)	C12—C11—H11B	109.2
C1—C2—H2	120.4	H11A—C11—H11B	107.9
C3—C2—H2	120.4	C11—C12—C7	109.1 (3)
C2—C3—C4	119.4 (4)	C11—C12—H12A	109.9
C2—C3—H3	120.3	C7—C12—H12A	109.9
C4—C3—H3	120.3	C11—C12—H12B	109.9
C5—C4—C3	121.3 (3)	C7—C12—H12B	109.9
C5—C4—H4	119.4	H12A—C12—H12B	108.3
C3—C4—H4	119.4	O5—C13—N2	122.5 (3)
C4—C5—C6	120.4 (3)	O5—C13—C14	119.3 (3)
C4—C5—H5	119.8	N2—C13—C14	117.9 (3)
C6—C5—H5	119.8	O6—C14—O7	127.5 (3)
C5—C6—C1	117.3 (3)	O6—C14—C13	121.3 (3)
C5—C6—S1	120.9 (2)	O7—C14—C13	111.0 (4)
C1—C6—S1	121.4 (2)	O7—C15—C16	107.5 (3)
N2—C7—C8	113.1 (2)	O7—C15—H15A	110.2
N2—C7—C12	112.9 (2)	C16—C15—H15A	110.2
C8—C7—C12	111.7 (3)	O7—C15—H15B	110.2
N2—C7—H7	106.2	C16—C15—H15B	110.2
C8—C7—H7	106.2	H15A—C15—H15B	108.5
C12—C7—H7	106.2	C15—C16—H16A	109.5
C7—C8—C9	109.8 (3)	C15—C16—H16B	109.5
C7—C8—H8A	109.7	H16A—C16—H16B	109.5
C9—C8—H8A	109.7	C15—C16—H16C	109.5
C7—C8—H8B	109.7	H16A—C16—H16C	109.5
C9—C8—H8B	109.7	H16B—C16—H16C	109.5
H8A—C8—H8B	108.2

O3—S1—N2—C13	135.1 (3)	O4—S1—C6—C1	93.4 (3)
O4—S1—N2—C13	5.1 (3)	N2—S1—C6—C1	−151.9 (2)
C6—S1—N2—C13	−112.9 (3)	C13—N2—C7—C8	−77.8 (4)
O3—S1—N2—C7	−35.9 (2)	S1—N2—C7—C8	93.3 (3)
O4—S1—N2—C7	−166.0 (2)	C13—N2—C7—C12	50.3 (4)
C6—S1—N2—C7	76.1 (2)	S1—N2—C7—C12	−138.7 (2)
O2—N1—C1—C2	130.9 (3)	N2—C7—C8—C9	−173.6 (3)
O1—N1—C1—C2	−47.8 (4)	C12—C7—C8—C9	57.7 (4)
O2—N1—C1—C6	−46.9 (4)	C7—C8—C9—C10	−56.1 (4)
O1—N1—C1—C6	134.4 (3)	C8—C9—C10—C11	55.5 (4)
C6—C1—C2—C3	1.1 (5)	C9—C10—C11—C12	−56.1 (4)
N1—C1—C2—C3	−176.7 (3)	C10—C11—C12—C7	56.6 (4)
C1—C2—C3—C4	0.2 (6)	N2—C7—C12—C11	173.7 (3)
C2—C3—C4—C5	−1.0 (6)	C8—C7—C12—C11	−57.5 (4)
C3—C4—C5—C6	0.4 (5)	C7—N2—C13—O5	14.3 (6)
C4—C5—C6—C1	0.8 (5)	S1—N2—C13—O5	−156.2 (3)
C4—C5—C6—S1	−172.5 (3)	C7—N2—C13—C14	−158.5 (3)
C2—C1—C6—C5	−1.6 (5)	S1—N2—C13—C14	30.9 (4)
N1—C1—C6—C5	176.1 (3)	C15—O7—C14—O6	−6.1 (5)
C2—C1—C6—S1	171.7 (3)	C15—O7—C14—C13	179.1 (3)
N1—C1—C6—S1	−10.6 (4)	O5—C13—C14—O6	−114.0 (5)
O3—S1—C6—C5	133.9 (2)	N2—C13—C14—O6	59.1 (5)
O4—S1—C6—C5	−93.6 (3)	O5—C13—C14—O7	61.2 (5)
N2—S1—C6—C5	21.2 (3)	N2—C13—C14—O7	−125.7 (3)
O3—S1—C6—C1	−39.2 (3)	C14—O7—C15—C16	176.2 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₂O₇S
M_r	384.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	10.962 (7), 12.352 (7), 13.879 (8)
β (°)	101.813 (11)
V (Å³)	1839.5 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.896, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	9177, 3240, 1813
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.01
No. of reflections	3240
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL and PLATON (Spek, 2003).

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page