Methyl 2-{[3-(4,6-dimethoxy­pyrimidin-2-yl)ureido]sulfonyl­meth­yl}benzoate

Xia, J.; Li, F.; Yin, L.; Yu, D.; Wu, D.

doi:10.1107/S1600536808005011

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o632

doi:10.1107/S1600536808005011

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Methyl 2-{[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonylmethyl}benzoate

Jin-yun Xia,^a Fang-shi Li,^a ^* Li-he Yin,^a Da-sheng Yu ^a and Deng-yu Wu ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 11 February 2008; accepted 21 February 2008; online 27 February 2008)

In the title compound, C₁₆H₁₈N₄O₇S, a synthetic sulfonylurea herbicide, there are intramolecular N—H⋯N and C—H⋯O hydrogen bonds. Intermolecular N—H⋯O and C—H⋯O hydrogen bonds form centrosymmetric dimers. The dihedral angle between the two rings is 50.00 (15)°.

Related literature

For related literature, see: Kong et al. (1990 ); Lee et al. (2002 ); Sabadie (1996 ).

Experimental

Crystal data

C₁₆H₁₈N₄O₇S
M_r = 410.41
Monoclinic, C 2/c
a = 33.831 (7) Å
b = 6.9020 (14) Å
c = 16.021 (3) Å
β = 104.48 (3)°
V = 3622.1 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 (2) K
0.40 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.914, T_max = 0.978
3325 measured reflections
3265 independent reflections
2421 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.156
S = 1.03
3265 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.86	1.94	2.648 (4)	138
N2—H2A⋯O5ⁱ	0.86	2.10	2.951 (3)	170
C9—H9B⋯O1	0.97	2.36	2.970 (4)	120
C15—H15C⋯O1ⁱ	0.96	2.43	3.068 (4)	124
Symmetry code: (i) $[-x, y, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005011/cf2185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005011/cf2185Isup2.hkl

checkCIF report

Comment top

The title compound, bensulfuron-methyl, belongs to the class of systemic sulfonylurea herbicides inhibiting acetolactate synthase, a key enzyme in the biosynthesis of the branched-chain amino acids of target plants (Lee et al., 2002). It is widely used in transplanted and direct-seeded rice fields to control most annual and perennial broadleaved weeds selectively (Sabadie, 1996).

We report here the crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the C3–C8 and C11/N3/C12/C13/C14/N4 rings is 50.00 (15)°. There are intramolecular N1—H1A···N3 and C9—H9B···O1 hydrogen bonds (Fig. 1), and intermolecular N—H···O and C—H···O hydrogen bonds form centrosymmetric dimers (Fig. 2).

Related literature top

For related literature, see: Kong et al. (1990); Lee et al. (2002); Sabadie (1996).

Experimental top

The title compound, (I), was prepared according to the literature method (Kong et al., 1990).

Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.2 g) in ethyl acetate (25 ml) and evaporating the solvent slowly at room temperature for about 15 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. A hydrogen-bonded dimer. Dashed lines indicate hydrogen bonds.

Methyl 2-{[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonylmethyl}benzoate top

Crystal data top

C₁₆H₁₈N₄O₇S	F(000) = 1712
M_r = 410.41	D_x = 1.505 Mg m⁻³
Monoclinic, C2/c	Melting point = 450–451 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 33.831 (7) Å	Cell parameters from 25 reflections
b = 6.9020 (14) Å	θ = 10–13°
c = 16.021 (3) Å	µ = 0.23 mm⁻¹
β = 104.48 (3)°	T = 298 K
V = 3622.1 (13) Å³	Needle, colorless
Z = 8	0.40 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.2°, θ_min = 1.2°
ω/2θ scans	h = −40→38
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.914, T_max = 0.978	l = 0→19
3325 measured reflections	3 standard reflections every 200 reflections
3265 independent reflections	intensity decay: none

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.08P)² + 5P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₈N₄O₇S	V = 3622.1 (13) Å³
M_r = 410.41	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.831 (7) Å	µ = 0.23 mm⁻¹
b = 6.9020 (14) Å	T = 298 K
c = 16.021 (3) Å	0.40 × 0.20 × 0.10 mm
β = 104.48 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2421 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.914, T_max = 0.978	3 standard reflections every 200 reflections
3325 measured reflections	intensity decay: none
3265 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
3265 reflections	Δρ_min = −0.31 e Å⁻³
253 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
S	0.12664 (2)	0.14338 (13)	0.69392 (5)	0.0401 (2)
N1	0.07804 (7)	0.1705 (4)	0.64572 (16)	0.0424 (7)
H1A	0.0719	0.1836	0.5906	0.051*
O1	0.15578 (7)	0.0798 (4)	0.92720 (16)	0.0557 (7)
C1	0.19376 (12)	−0.2563 (5)	0.9629 (3)	0.0570 (10)
H1B	0.2121	−0.3646	0.9704	0.085*
H1C	0.1676	−0.2946	0.9278	0.085*
H1D	0.1909	−0.2139	1.0182	0.085*
O2	0.20987 (7)	−0.0991 (3)	0.92109 (16)	0.0484 (6)
N2	0.00822 (7)	0.1970 (4)	0.63164 (16)	0.0388 (6)
H2A	−0.0114	0.1857	0.6565	0.047*
C2	0.18727 (9)	0.0615 (5)	0.90655 (19)	0.0379 (7)
N3	0.02372 (7)	0.2300 (4)	0.49733 (16)	0.0363 (6)
O3	0.13329 (8)	−0.0390 (4)	0.73670 (16)	0.0576 (7)
C3	0.20669 (9)	0.2172 (5)	0.86550 (18)	0.0356 (7)
O4	0.14650 (7)	0.1838 (4)	0.62677 (15)	0.0542 (7)
N4	−0.04352 (7)	0.2765 (4)	0.51521 (16)	0.0375 (6)
C4	0.24906 (9)	0.2405 (5)	0.8922 (2)	0.0432 (8)
H4C	0.2647	0.1513	0.9300	0.052*
O5	0.05149 (7)	0.1570 (4)	0.76305 (14)	0.0509 (6)
C5	0.26803 (10)	0.3949 (5)	0.8631 (2)	0.0470 (8)
H5A	0.2962	0.4101	0.8819	0.056*
O6	0.03580 (7)	0.2645 (4)	0.36258 (15)	0.0531 (6)
C6	0.24518 (11)	0.5258 (6)	0.8063 (2)	0.0505 (9)
H6A	0.2578	0.6302	0.7870	0.061*
O7	−0.09468 (7)	0.3699 (4)	0.39861 (15)	0.0508 (6)
C7	0.20337 (10)	0.5023 (5)	0.7779 (2)	0.0468 (8)
H7A	0.1883	0.5896	0.7382	0.056*
C8	0.18338 (9)	0.3511 (5)	0.80731 (19)	0.0363 (7)
C9	0.13757 (9)	0.3323 (5)	0.7722 (2)	0.0406 (8)
H9A	0.1264	0.4537	0.7460	0.049*
H9B	0.1249	0.3034	0.8188	0.049*
C10	0.04638 (9)	0.1743 (5)	0.6850 (2)	0.0369 (7)
C11	−0.00401 (9)	0.2356 (4)	0.54321 (19)	0.0341 (7)
C12	0.00998 (10)	0.2704 (5)	0.4133 (2)	0.0388 (7)
C13	−0.03018 (10)	0.3179 (5)	0.3764 (2)	0.0438 (8)
H13A	−0.0395	0.3469	0.3181	0.053*
C14	−0.05548 (9)	0.3198 (5)	0.4314 (2)	0.0391 (7)
C15	−0.12294 (10)	0.3408 (6)	0.4504 (2)	0.0573 (10)
H15A	−0.1496	0.3834	0.4193	0.086*
H15B	−0.1143	0.4138	0.5028	0.086*
H15C	−0.1239	0.2056	0.4639	0.086*
C16	0.07680 (10)	0.1963 (6)	0.3980 (2)	0.0597 (10)
H16A	0.0918	0.2013	0.3545	0.090*
H16B	0.0760	0.0652	0.4175	0.090*
H16C	0.0899	0.2770	0.4457	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0287 (4)	0.0485 (5)	0.0398 (4)	0.0025 (3)	0.0022 (3)	−0.0034 (4)
N1	0.0293 (13)	0.0636 (19)	0.0332 (14)	−0.0023 (13)	0.0057 (11)	0.0033 (13)
O1	0.0422 (14)	0.0684 (17)	0.0634 (15)	0.0099 (12)	0.0260 (12)	0.0167 (13)
C1	0.067 (2)	0.041 (2)	0.065 (2)	−0.0069 (18)	0.0199 (19)	0.0080 (19)
O2	0.0434 (13)	0.0434 (14)	0.0610 (15)	0.0055 (10)	0.0178 (11)	0.0100 (11)
N2	0.0292 (13)	0.0450 (16)	0.0394 (14)	0.0004 (11)	0.0035 (11)	0.0083 (12)
C2	0.0350 (17)	0.0447 (18)	0.0313 (15)	0.0025 (14)	0.0032 (13)	−0.0006 (14)
N3	0.0344 (14)	0.0381 (15)	0.0353 (14)	−0.0032 (11)	0.0069 (11)	−0.0003 (11)
O3	0.0556 (16)	0.0440 (15)	0.0620 (16)	0.0068 (12)	−0.0061 (12)	0.0009 (12)
C3	0.0359 (16)	0.0420 (18)	0.0281 (14)	−0.0003 (14)	0.0067 (12)	−0.0035 (13)
O4	0.0377 (13)	0.0835 (19)	0.0434 (13)	−0.0003 (12)	0.0140 (10)	−0.0076 (12)
N4	0.0319 (13)	0.0339 (14)	0.0419 (15)	−0.0018 (11)	0.0001 (11)	0.0019 (12)
C4	0.0339 (16)	0.055 (2)	0.0373 (17)	0.0008 (15)	0.0018 (13)	−0.0002 (16)
O5	0.0351 (12)	0.0769 (18)	0.0383 (13)	0.0013 (12)	0.0046 (10)	0.0061 (12)
C5	0.0336 (17)	0.062 (2)	0.0423 (18)	−0.0094 (16)	0.0041 (14)	−0.0014 (17)
O6	0.0460 (14)	0.0707 (17)	0.0428 (13)	0.0023 (12)	0.0117 (11)	0.0010 (12)
C6	0.049 (2)	0.057 (2)	0.0463 (19)	−0.0161 (17)	0.0120 (16)	0.0005 (17)
O7	0.0359 (12)	0.0585 (15)	0.0513 (14)	0.0048 (11)	−0.0016 (10)	0.0134 (12)
C7	0.0469 (19)	0.050 (2)	0.0393 (17)	0.0003 (16)	0.0035 (15)	0.0036 (16)
C8	0.0306 (15)	0.0397 (17)	0.0360 (16)	−0.0009 (13)	0.0035 (12)	−0.0060 (14)
C9	0.0344 (16)	0.0445 (19)	0.0406 (17)	0.0049 (14)	0.0050 (13)	−0.0014 (15)
C10	0.0304 (15)	0.0371 (17)	0.0412 (18)	−0.0007 (13)	0.0052 (13)	0.0015 (14)
C11	0.0312 (15)	0.0291 (16)	0.0389 (16)	−0.0024 (12)	0.0028 (13)	0.0013 (13)
C12	0.0439 (18)	0.0330 (17)	0.0385 (17)	−0.0033 (14)	0.0083 (14)	−0.0030 (14)
C13	0.0460 (19)	0.045 (2)	0.0340 (16)	−0.0047 (15)	−0.0020 (14)	0.0006 (14)
C14	0.0363 (17)	0.0323 (17)	0.0433 (18)	−0.0011 (13)	−0.0001 (14)	0.0054 (14)
C15	0.0384 (19)	0.068 (3)	0.062 (2)	0.0021 (18)	0.0057 (17)	0.011 (2)
C16	0.0396 (19)	0.081 (3)	0.057 (2)	−0.0040 (19)	0.0105 (16)	−0.009 (2)

Geometric parameters (Å, º) top

S—O3	1.424 (3)	O5—C10	1.224 (4)
S—O4	1.431 (2)	C5—C6	1.374 (5)
S—N1	1.643 (3)	C5—H5A	0.930
S—C9	1.782 (3)	O6—C12	1.334 (4)
N1—C10	1.372 (4)	O6—C16	1.440 (4)
N1—H1A	0.860	C6—C7	1.383 (5)
O1—C2	1.199 (4)	C6—H6A	0.930
C1—O2	1.451 (4)	O7—C14	1.344 (4)
C1—H1B	0.960	O7—C15	1.428 (4)
C1—H1C	0.960	C7—C8	1.388 (5)
C1—H1D	0.960	C7—H7A	0.930
O2—C2	1.333 (4)	C8—C9	1.516 (4)
N2—C10	1.368 (4)	C9—H9A	0.970
N2—C11	1.399 (4)	C9—H9B	0.970
N2—H2A	0.860	C12—C13	1.379 (4)
C2—C3	1.495 (5)	C13—C14	1.373 (5)
N3—C11	1.329 (4)	C13—H13A	0.930
N3—C12	1.339 (4)	C15—H15A	0.960
C3—C4	1.399 (4)	C15—H15B	0.960
C3—C8	1.406 (4)	C15—H15C	0.960
N4—C11	1.330 (4)	C16—H16A	0.960
N4—C14	1.336 (4)	C16—H16B	0.960
C4—C5	1.384 (5)	C16—H16C	0.960
C4—H4C	0.930

O3—S—O4	119.13 (17)	C6—C7—H7A	119.3
O3—S—N1	110.25 (15)	C8—C7—H7A	119.3
O4—S—N1	103.13 (14)	C7—C8—C3	118.6 (3)
O3—S—C9	109.17 (16)	C7—C8—C9	118.5 (3)
O4—S—C9	109.40 (16)	C3—C8—C9	122.8 (3)
N1—S—C9	104.73 (15)	C8—C9—S	109.7 (2)
C10—N1—S	126.2 (2)	C8—C9—H9A	109.7
C10—N1—H1A	116.9	S—C9—H9A	109.7
S—N1—H1A	116.9	C8—C9—H9B	109.7
O2—C1—H1B	109.5	S—C9—H9B	109.7
O2—C1—H1C	109.5	H9A—C9—H9B	108.2
H1B—C1—H1C	109.5	O5—C10—N2	121.3 (3)
O2—C1—H1D	109.5	O5—C10—N1	122.7 (3)
H1B—C1—H1D	109.5	N2—C10—N1	116.0 (3)
H1C—C1—H1D	109.5	N3—C11—N4	127.5 (3)
C2—O2—C1	115.9 (3)	N3—C11—N2	118.9 (3)
C10—N2—C11	130.5 (3)	N4—C11—N2	113.6 (3)
C10—N2—H2A	114.8	O6—C12—N3	119.4 (3)
C11—N2—H2A	114.8	O6—C12—C13	118.1 (3)
O1—C2—O2	123.4 (3)	N3—C12—C13	122.5 (3)
O1—C2—C3	124.3 (3)	C14—C13—C12	115.6 (3)
O2—C2—C3	112.2 (3)	C14—C13—H13A	122.2
C11—N3—C12	115.7 (3)	C12—C13—H13A	122.2
C4—C3—C8	119.3 (3)	N4—C14—O7	118.1 (3)
C4—C3—C2	118.5 (3)	N4—C14—C13	124.2 (3)
C8—C3—C2	121.9 (3)	O7—C14—C13	117.7 (3)
C11—N4—C14	114.4 (3)	O7—C15—H15A	109.5
C5—C4—C3	120.8 (3)	O7—C15—H15B	109.5
C5—C4—H4C	119.6	H15A—C15—H15B	109.5
C3—C4—H4C	119.6	O7—C15—H15C	109.5
C6—C5—C4	119.8 (3)	H15A—C15—H15C	109.5
C6—C5—H5A	120.1	H15B—C15—H15C	109.5
C4—C5—H5A	120.1	O6—C16—H16A	109.5
C12—O6—C16	118.8 (3)	O6—C16—H16B	109.5
C5—C6—C7	120.1 (3)	H16A—C16—H16B	109.5
C5—C6—H6A	120.0	O6—C16—H16C	109.5
C7—C6—H6A	120.0	H16A—C16—H16C	109.5
C14—O7—C15	118.4 (3)	H16B—C16—H16C	109.5
C6—C7—C8	121.4 (3)

O3—S—N1—C10	61.5 (3)	N1—S—C9—C8	−167.4 (2)
O4—S—N1—C10	−170.2 (3)	C11—N2—C10—O5	173.7 (3)
C9—S—N1—C10	−55.8 (3)	C11—N2—C10—N1	−6.9 (5)
C1—O2—C2—O1	1.1 (5)	S—N1—C10—O5	−0.1 (5)
C1—O2—C2—C3	178.5 (3)	S—N1—C10—N2	−179.5 (2)
O1—C2—C3—C4	139.0 (3)	C12—N3—C11—N4	0.0 (5)
O2—C2—C3—C4	−38.4 (4)	C12—N3—C11—N2	−179.3 (3)
O1—C2—C3—C8	−34.9 (5)	C14—N4—C11—N3	−1.4 (5)
O2—C2—C3—C8	147.7 (3)	C14—N4—C11—N2	178.0 (3)
C8—C3—C4—C5	1.0 (5)	C10—N2—C11—N3	8.8 (5)
C2—C3—C4—C5	−173.1 (3)	C10—N2—C11—N4	−170.6 (3)
C3—C4—C5—C6	−0.9 (5)	C16—O6—C12—N3	6.0 (5)
C4—C5—C6—C7	−0.5 (5)	C16—O6—C12—C13	−173.8 (3)
C5—C6—C7—C8	1.9 (5)	C11—N3—C12—O6	−178.8 (3)
C6—C7—C8—C3	−1.7 (5)	C11—N3—C12—C13	1.0 (5)
C6—C7—C8—C9	−179.0 (3)	O6—C12—C13—C14	179.3 (3)
C4—C3—C8—C7	0.3 (4)	N3—C12—C13—C14	−0.5 (5)
C2—C3—C8—C7	174.2 (3)	C11—N4—C14—O7	−177.5 (3)
C4—C3—C8—C9	177.5 (3)	C11—N4—C14—C13	1.9 (5)
C2—C3—C8—C9	−8.7 (5)	C15—O7—C14—N4	−11.2 (4)
C7—C8—C9—S	102.8 (3)	C15—O7—C14—C13	169.4 (3)
C3—C8—C9—S	−74.3 (3)	C12—C13—C14—N4	−1.0 (5)
O3—S—C9—C8	74.5 (3)	C12—C13—C14—O7	178.4 (3)
O4—S—C9—C8	−57.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	1.94	2.648 (4)	138
N2—H2A···O5ⁱ	0.86	2.10	2.951 (3)	170
C9—H9B···O1	0.97	2.36	2.970 (4)	120
C15—H15C···O1ⁱ	0.96	2.43	3.068 (4)	124

Symmetry code: (i) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₄O₇S
M_r	410.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	33.831 (7), 6.9020 (14), 16.021 (3)
β (°)	104.48 (3)
V (Å³)	3622.1 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.914, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	3325, 3265, 2421
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.156, 1.03
No. of reflections	3265
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.31

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	1.94	2.648 (4)	138
N2—H2A···O5ⁱ	0.86	2.10	2.951 (3)	170
C9—H9B···O1	0.97	2.36	2.970 (4)	120
C15—H15C···O1ⁱ	0.96	2.43	3.068 (4)	124

Symmetry code: (i) −x, y, −z+3/2.

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kong, F., Hu, X., Wang, L., Tao, Z., Wang, X. & Cao, W. (1990). Huaxue Shijie, 31, 211–213. CAS Google Scholar
Lee, J. K., Ahn, K. C., Park, O. S., Ko, Y. K. & Kim, D.-W. (2002). J. Agric. Food Chem. 50, 1791–1803. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sabadie, J. (1996). Weed Res. 36, 441–448. CrossRef CAS Web of Science 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 3| March 2008| Page o632

doi:10.1107/S1600536808005011

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