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Acta Cryst. (2008). E64, o1248    [ doi:10.1107/S1600536808017029 ]

Ethyl 2-{N-[N-(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate

C. Lu, F. Li, D.-S. Yu, W. Yao and Y.-H. Liu

Abstract top

The asymmetric unit of the title compound, C15H15ClN4O6S, contains two independent molecules, in which the pyrimidine and benzene rings are oriented at dihedral angles of 75.21 (3) and 86.00 (3)°. Intramolecular N-H...N and C-H...O hydrogen bonds result in the formation of two five- and two six-membered rings. The six-membered rings have flattened-boat conformations, while the five-membered rings adopt envelope conformations. In the crystal structure, intermolecular N-H...O hydrogen bonds link the molecules.

Comment top

The title compound, (I), is a highly effective postemergence sulfonylurea herbicide used to control many annual broadleaf weeds in soybean fields (Zhao et al., 2006). As part of our studies in this area, we report herein its crystal structure.

The asymmetric unit of (I) (Fig. 1) contains two independent molecules. The bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C4-C9), B (N3/N4/C11-C14) and C (C19-C24), D (N7/N8/C26-C29) are, of course, planar, and the dihedral angles between them are A/B = 75.21 (3)° and C/D = 86.00 (3)°. The intramolecular N-H···N and C-H···O hydrogen bonds (Table 1) result in the formation of two five- and two six-membered rings: E (N1-N3/C10/C11/H1A), F (S1/O4/C8/C9/H8A), G (N5-N7/C25/C26/H5B) and H (S2/O9/C20/C21/H21A). Rings E and G adopt flattened-boat conformations, having total puckering amplitudes, QT, of 0.139 (3) and 0.117 (3) Å (Cremer & Pople, 1975), while rings F and H have envelope conformations, with O4 and O9 atoms displaced by 0.291 (3) and -0.182 (3) Å from the planes of the other ring atoms, respectively.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Zhao et al. (2006); Li & Liu (1995). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound, (I), was prepared according to the literature method (Li & Liu, 1995). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.1 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Refinement top

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
[Figure 2] Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.
Ethyl 2-{N-[N-(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate top
Crystal data top
C15H15ClN4O6SZ = 4
Mr = 414.83F000 = 856
Triclinic, P1Dx = 1.439 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.8210 (16) ÅCell parameters from 25 reflections
b = 12.310 (3) Åθ = 10–13º
c = 20.200 (4) ŵ = 0.35 mm−1
α = 94.97 (3)ºT = 298 (2) K
β = 97.58 (3)ºBlock, colorless
γ = 93.76 (3)º0.40 × 0.30 × 0.10 mm
V = 1914.7 (7) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.069
Radiation source: fine-focus sealed tubeθmax = 25.2º
Monochromator: graphiteθmin = 1.0º
T = 298(2) Kh = −9→9
ω/2θ scansk = −14→14
Absorption correction: ψ scan
(North et al., 1968)		l = 0→24
Tmin = 0.873, Tmax = 0.9663 standard reflections
7430 measured reflections every 120 min
6882 independent reflections intensity decay: none
3809 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.088H-atom parameters constrained
wR(F2) = 0.209  w = 1/[σ2(Fo2) + (0.06P)2 + 3P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
6882 reflectionsΔρmax = 0.39 e Å−3
451 parametersΔρmin = −0.92 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C15H15ClN4O6Sγ = 93.76 (3)º
Mr = 414.83V = 1914.7 (7) Å3
Triclinic, P1Z = 4
a = 7.8210 (16) ÅMo Kα
b = 12.310 (3) ŵ = 0.35 mm−1
c = 20.200 (4) ÅT = 298 (2) K
α = 94.97 (3)º0.40 × 0.30 × 0.10 mm
β = 97.58 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		3809 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.069
Tmin = 0.873, Tmax = 0.9663 standard reflections
7430 measured reflections every 120 min
6882 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.088? restraints
wR(F2) = 0.209H-atom parameters constrained
S = 1.07Δρmax = 0.39 e Å−3
6882 reflectionsΔρmin = −0.92 e Å−3
451 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 > 2sigma(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
xyzUiso*/Ueq
Cl10.2819 (3)1.35508 (17)0.20491 (14)0.1456 (9)
Cl2−0.2214 (4)1.36337 (15)0.18268 (12)0.1378 (9)
S10.30971 (16)0.69683 (11)0.07830 (8)0.0633 (4)
S2−0.4009 (2)1.21087 (14)0.41116 (9)0.0851 (5)
O10.6496 (7)0.6052 (5)0.2354 (3)0.121
O20.5614 (6)0.7692 (4)0.2171 (2)0.1023 (14)
O30.2506 (5)0.6505 (3)0.1335 (2)0.0809 (11)
O40.2122 (5)0.6758 (3)0.0137 (2)0.0790 (11)
O50.4435 (4)0.8758 (3)0.00933 (17)0.0617 (9)
O60.1314 (6)0.9834 (4)0.27791 (19)0.0895 (12)
O70.1026 (6)1.3566 (4)0.4533 (2)0.1042 (14)
O8−0.0191 (6)1.2479 (4)0.3635 (2)0.0983 (14)
O9−0.5648 (6)1.1767 (5)0.4287 (3)0.1230 (18)
O10−0.3643 (6)1.3245 (4)0.4050 (2)0.1082 (15)
O11−0.4315 (5)0.9729 (3)0.3604 (2)0.0879 (12)
O12−0.1102 (5)1.0051 (3)0.0628 (2)0.087
N10.3246 (5)0.8291 (3)0.0994 (2)0.0621 (11)
H1A0.29270.85300.13680.074*
N20.3823 (5)1.0128 (3)0.0822 (2)0.0562 (10)
H2A0.42461.05870.05780.067*
N30.2572 (5)0.9970 (4)0.1804 (2)0.0645 (11)
N40.3277 (5)1.1683 (4)0.1435 (2)0.0727 (12)
N5−0.3771 (5)1.1487 (4)0.3380 (2)0.0696 (12)
H5B−0.35911.18870.30640.084*
N6−0.3321 (5)1.0026 (4)0.2635 (2)0.0664 (11)
H6B−0.34060.93280.25430.080*
N7−0.2656 (6)1.1691 (4)0.2210 (2)0.0780 (13)
N8−0.2204 (5)0.9995 (4)0.1625 (2)0.0710 (12)
C10.7097 (10)0.5750 (6)0.3555 (4)0.110
H1B0.65470.58300.39530.166*
H1C0.82830.60360.36580.166*
H1D0.70480.49890.33960.166*
C20.6224 (10)0.6335 (6)0.3050 (3)0.105
H2B0.65680.71080.31630.127*
H2C0.49930.62350.30710.127*
C30.6109 (8)0.6821 (5)0.1952 (4)0.0849 (19)
C40.6389 (7)0.6488 (4)0.1286 (4)0.0716 (15)
C50.8039 (7)0.6113 (4)0.1169 (4)0.087 (2)
H5A0.88780.60410.15300.104*
C60.8363 (9)0.5873 (5)0.0558 (6)0.103 (3)
H6A0.94050.55800.04980.123*
C70.7241 (9)0.6033 (5)0.0002 (4)0.095 (2)
H7A0.75590.5902−0.04240.113*
C80.5624 (7)0.6392 (4)0.0077 (4)0.0794 (17)
H8A0.48280.6478−0.02960.095*
C90.5227 (6)0.6617 (4)0.0718 (3)0.0610 (13)
C100.3871 (6)0.9035 (4)0.0590 (3)0.0562 (12)
C110.3213 (6)1.0596 (4)0.1379 (3)0.0585 (12)
C120.2003 (7)1.0443 (5)0.2328 (3)0.0688 (15)
C130.2059 (8)1.1576 (6)0.2442 (3)0.0843 (18)
H13A0.16851.19250.28180.101*
C140.2698 (8)1.2139 (5)0.1968 (3)0.0809 (17)
C150.1267 (10)0.8714 (7)0.2624 (4)0.113 (2)
H15A0.07620.83470.29600.169*
H15B0.24220.85020.26100.169*
H15C0.05840.85150.21950.169*
C160.2150 (10)1.5357 (6)0.4433 (4)0.119
H16A0.27301.58230.41610.178*
H16B0.28471.53500.48610.178*
H16C0.10531.56260.44970.178*
C170.1872 (10)1.4226 (6)0.4092 (4)0.110
H17A0.11491.42170.36620.132*
H17B0.29691.39470.40170.132*
C180.0078 (8)1.2714 (5)0.4211 (3)0.0780 (16)
C19−0.0646 (8)1.2030 (5)0.4724 (3)0.0746 (15)
C20−0.2409 (8)1.1672 (5)0.4701 (3)0.0764 (15)
C21−0.2891 (9)1.1016 (5)0.5153 (3)0.0913 (18)
H21A−0.40581.08000.51420.110*
C22−0.1676 (12)1.0649 (6)0.5642 (4)0.110 (2)
H22A−0.20281.01710.59390.132*
C23−0.0037 (11)1.0987 (7)0.5676 (4)0.109 (2)
H23A0.07581.07470.60050.131*
C240.0571 (10)1.1704 (6)0.5229 (4)0.106 (2)
H24A0.17341.19500.52700.127*
C25−0.3841 (7)1.0362 (5)0.3238 (3)0.0684 (14)
C26−0.2682 (6)1.0601 (5)0.2143 (3)0.0675 (13)
C27−0.2115 (9)1.2230 (6)0.1711 (4)0.0914 (18)
C28−0.1619 (9)1.1722 (6)0.1197 (4)0.0905 (18)
H28A−0.12511.21070.08590.109*
C29−0.1637 (7)1.0629 (5)0.1155 (3)0.0747 (15)
C30−0.1119 (5)0.8938 (3)0.0581 (2)0.0413 (10)
H30A−0.07250.86800.01700.062*
H30B−0.22760.86290.05870.062*
H30C−0.03690.87200.09540.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.163 (2)0.0865 (13)0.183 (2)−0.0031 (13)0.0484 (17)−0.0403 (14)
Cl20.199 (2)0.0701 (12)0.1447 (19)0.0120 (13)0.0191 (16)0.0190 (11)
S10.0420 (7)0.0561 (8)0.0927 (10)−0.0030 (6)0.0109 (7)0.0143 (7)
S20.0714 (10)0.0853 (12)0.0964 (12)0.0066 (8)0.0153 (9)−0.0094 (9)
O10.1210.1210.1210.0090.0170.012
O20.131 (4)0.064 (3)0.109 (3)0.008 (3)0.009 (3)−0.001 (2)
O30.066 (2)0.070 (2)0.113 (3)0.0030 (19)0.025 (2)0.030 (2)
O40.071 (3)0.078 (3)0.085 (3)−0.009 (2)0.007 (2)0.010 (2)
O50.058 (2)0.060 (2)0.069 (2)0.0027 (16)0.0199 (18)0.0014 (17)
O60.092 (3)0.121 (4)0.062 (2)0.027 (3)0.018 (2)0.018 (2)
O70.100 (3)0.094 (3)0.112 (4)−0.023 (3)0.021 (3)−0.013 (3)
O80.099 (3)0.114 (4)0.077 (3)−0.015 (3)0.014 (2)−0.007 (3)
O90.072 (3)0.151 (5)0.145 (4)−0.003 (3)0.041 (3)−0.026 (3)
O100.109 (4)0.072 (3)0.134 (4)0.019 (3)−0.010 (3)−0.019 (3)
O110.093 (3)0.082 (3)0.088 (3)−0.017 (2)0.018 (2)0.011 (2)
O120.0870.0870.0870.0070.0120.008
N10.050 (2)0.060 (3)0.081 (3)0.013 (2)0.017 (2)0.012 (2)
N20.045 (2)0.059 (3)0.066 (3)0.0026 (19)0.0112 (19)0.010 (2)
N30.051 (3)0.082 (3)0.061 (3)0.020 (2)0.002 (2)0.009 (2)
N40.054 (3)0.066 (3)0.093 (3)−0.002 (2)0.005 (2)−0.010 (3)
N50.068 (3)0.072 (3)0.064 (3)0.006 (2)−0.005 (2)−0.002 (2)
N60.067 (3)0.065 (3)0.063 (3)0.000 (2)−0.005 (2)0.010 (2)
N70.082 (3)0.078 (3)0.073 (3)0.004 (3)0.002 (2)0.014 (2)
N80.053 (3)0.088 (3)0.067 (3)0.004 (2)−0.007 (2)0.005 (2)
C10.1100.1100.1100.0090.0150.011
C20.1050.1050.1050.0080.0150.010
C30.079 (4)0.062 (4)0.109 (5)0.000 (3)−0.015 (4)0.034 (4)
C40.051 (3)0.045 (3)0.116 (5)−0.002 (2)0.002 (3)0.012 (3)
C50.048 (3)0.047 (3)0.164 (7)−0.004 (3)0.015 (4)0.001 (4)
C60.048 (4)0.056 (4)0.205 (9)0.000 (3)0.043 (5)−0.019 (5)
C70.071 (4)0.052 (3)0.163 (7)−0.015 (3)0.057 (5)−0.021 (4)
C80.060 (4)0.058 (3)0.120 (5)−0.009 (3)0.014 (3)0.013 (3)
C90.049 (3)0.041 (3)0.090 (4)−0.011 (2)0.010 (3)0.005 (3)
C100.036 (3)0.056 (3)0.077 (4)0.010 (2)0.005 (2)0.014 (3)
C110.043 (3)0.066 (3)0.063 (3)0.005 (2)−0.004 (2)0.004 (3)
C120.052 (3)0.098 (5)0.054 (3)0.014 (3)−0.003 (3)0.006 (3)
C130.067 (4)0.113 (6)0.069 (4)0.015 (4)0.007 (3)−0.017 (4)
C140.069 (4)0.079 (4)0.086 (4)0.000 (3)−0.006 (3)−0.013 (3)
C150.126 (6)0.122 (7)0.096 (5)−0.004 (5)0.026 (4)0.037 (5)
C160.1190.1190.1190.0090.0160.011
C170.1100.1100.1100.0090.0150.011
C180.064 (4)0.082 (4)0.084 (4)−0.007 (3)0.012 (3)−0.007 (3)
C190.078 (4)0.080 (4)0.065 (3)−0.009 (3)0.017 (3)0.001 (3)
C200.076 (3)0.075 (4)0.074 (3)−0.006 (3)0.008 (3)−0.006 (3)
C210.094 (4)0.095 (4)0.083 (4)−0.019 (3)0.025 (3)0.001 (3)
C220.138 (5)0.110 (5)0.075 (4)−0.012 (4)0.008 (4)0.006 (3)
C230.127 (5)0.117 (5)0.079 (4)0.015 (4)−0.008 (4)0.015 (4)
C240.094 (4)0.114 (5)0.099 (5)−0.002 (4)−0.010 (3)−0.005 (4)
C250.056 (3)0.074 (4)0.073 (4)0.002 (3)−0.002 (3)0.011 (3)
C260.042 (3)0.091 (4)0.064 (3)−0.002 (3)−0.004 (2)0.003 (3)
C270.088 (4)0.101 (4)0.082 (4)0.012 (3)−0.004 (3)0.013 (3)
C280.092 (4)0.086 (4)0.090 (4)−0.002 (3)0.004 (3)0.017 (3)
C290.058 (3)0.099 (4)0.063 (3)0.010 (3)−0.005 (3)0.002 (3)
C300.030 (2)0.050 (3)0.041 (2)0.0020 (18)0.0019 (17)−0.0027 (18)
Geometric parameters (Å, °) top
Cl1—C141.727 (7)Cl2—C271.732 (7)
S1—O31.413 (4)S2—O91.421 (5)
S1—O41.416 (4)S2—O101.429 (5)
S1—N11.639 (4)S2—N51.643 (4)
S1—C91.767 (5)S2—C201.755 (6)
O1—C31.325 (7)O7—C181.314 (7)
O1—C21.464 (8)O7—C171.450 (8)
O2—C31.230 (8)O8—C181.161 (7)
O5—C101.180 (6)O11—C251.195 (6)
O6—C121.370 (7)O12—C291.356 (6)
O6—C151.384 (8)O12—C301.364 (5)
N1—C101.386 (6)N5—C251.385 (7)
N1—H1A0.8600N5—H5B0.8600
N2—C111.374 (6)N6—C251.373 (7)
N2—C101.391 (6)N6—C261.395 (7)
N2—H2A0.8600N6—H6B0.8600
N3—C121.306 (6)N7—C261.335 (7)
N3—C111.327 (6)N7—C271.352 (8)
N4—C141.319 (7)N8—C261.341 (7)
N4—C111.331 (6)N8—C291.380 (7)
C1—C21.427 (7)C16—C171.488 (9)
C1—H1B0.9600C16—H16A0.9600
C1—H1C0.9600C16—H16B0.9600
C1—H1D0.9600C16—H16C0.9600
C2—H2B0.9700C17—H17A0.9700
C2—H2C0.9700C17—H17B0.9700
C3—C41.422 (9)C18—C191.533 (8)
C4—C91.393 (8)C19—C241.404 (9)
C4—C51.440 (8)C19—C201.413 (8)
C5—C61.305 (10)C20—C211.344 (8)
C5—H5A0.9300C21—C221.403 (10)
C6—C71.369 (10)C21—H21A0.9300
C6—H6A0.9300C22—C231.313 (10)
C7—C81.389 (8)C22—H22A0.9300
C7—H7A0.9300C23—C241.420 (10)
C8—C91.381 (8)C23—H23A0.9300
C8—H8A0.9300C24—H24A0.9300
C12—C131.391 (8)C27—C281.282 (9)
C13—C141.357 (8)C28—C291.339 (8)
C13—H13A0.9300C28—H28A0.9300
C15—H15A0.9600C30—H30A0.9600
C15—H15B0.9600C30—H30B0.9600
C15—H15C0.9600C30—H30C0.9600
O3—S1—O4120.0 (2)O9—S2—O10118.1 (3)
O3—S1—N1104.5 (2)O9—S2—N5109.7 (3)
O4—S1—N1108.2 (2)O10—S2—N5104.9 (3)
O3—S1—C9109.6 (2)O9—S2—C20107.9 (3)
O4—S1—C9107.6 (3)O10—S2—C20109.1 (3)
N1—S1—C9106.0 (2)N5—S2—C20106.5 (2)
C3—O1—C2113.9 (6)C18—O7—C17113.0 (5)
C12—O6—C15114.6 (5)C29—O12—C30121.9 (5)
C10—N1—S1122.1 (4)C25—N5—S2124.5 (4)
C10—N1—H1A119.0C25—N5—H5B117.8
S1—N1—H1A119.0S2—N5—H5B117.8
C11—N2—C10130.6 (4)C25—N6—C26132.3 (5)
C11—N2—H2A114.7C25—N6—H6B113.9
C10—N2—H2A114.7C26—N6—H6B113.9
C12—N3—C11118.6 (5)C26—N7—C27117.3 (5)
C14—N4—C11115.5 (5)C26—N8—C29112.1 (5)
C2—C1—H1B109.5C17—C16—H16A109.5
C2—C1—H1C109.5C17—C16—H16B109.5
H1B—C1—H1C109.5H16A—C16—H16B109.5
C2—C1—H1D109.5C17—C16—H16C109.5
H1B—C1—H1D109.5H16A—C16—H16C109.5
H1C—C1—H1D109.5H16B—C16—H16C109.5
C1—C2—O1117.7 (6)O7—C17—C16106.5 (6)
C1—C2—H2B107.9O7—C17—H17A110.4
O1—C2—H2B107.9C16—C17—H17A110.4
C1—C2—H2C107.9O7—C17—H17B110.4
O1—C2—H2C107.9C16—C17—H17B110.4
H2B—C2—H2C107.2H17A—C17—H17B108.6
O2—C3—O1120.8 (7)O8—C18—O7127.7 (6)
O2—C3—C4128.4 (6)O8—C18—C19123.5 (6)
O1—C3—C4110.8 (6)O7—C18—C19108.8 (5)
C9—C4—C3123.8 (5)C24—C19—C20119.1 (6)
C9—C4—C5116.4 (6)C24—C19—C18116.2 (6)
C3—C4—C5119.4 (6)C20—C19—C18124.6 (6)
C6—C5—C4120.4 (7)C21—C20—C19119.8 (6)
C6—C5—H5A119.8C21—C20—S2118.8 (5)
C4—C5—H5A119.8C19—C20—S2121.3 (5)
C5—C6—C7123.0 (6)C20—C21—C22121.6 (7)
C5—C6—H6A118.5C20—C21—H21A119.2
C7—C6—H6A118.5C22—C21—H21A119.2
C6—C7—C8119.6 (7)C23—C22—C21119.3 (7)
C6—C7—H7A120.2C23—C22—H22A120.3
C8—C7—H7A120.2C21—C22—H22A120.3
C9—C8—C7118.4 (7)C22—C23—C24122.6 (8)
C9—C8—H8A120.8C22—C23—H23A118.7
C7—C8—H8A120.8C24—C23—H23A118.7
C8—C9—C4122.1 (5)C19—C24—C23117.6 (7)
C8—C9—S1116.4 (4)C19—C24—H24A121.2
C4—C9—S1121.3 (4)C23—C24—H24A121.2
O5—C10—N1122.3 (5)O11—C25—N6122.1 (6)
O5—C10—N2122.7 (5)O11—C25—N5123.4 (6)
N1—C10—N2114.9 (5)N6—C25—N5114.4 (5)
N3—C11—N4124.6 (5)N7—C26—N8125.6 (5)
N3—C11—N2120.2 (5)N7—C26—N6118.2 (5)
N4—C11—N2115.2 (5)N8—C26—N6116.1 (5)
N3—C12—O6120.8 (6)C28—C27—N7121.7 (7)
N3—C12—C13121.3 (6)C28—C27—Cl2124.5 (6)
O6—C12—C13117.9 (5)N7—C27—Cl2113.9 (5)
C14—C13—C12115.4 (5)C27—C28—C29119.2 (7)
C14—C13—H13A122.3C27—C28—H28A120.4
C12—C13—H13A122.3C29—C28—H28A120.4
N4—C14—C13124.6 (6)C28—C29—O12121.7 (6)
N4—C14—Cl1115.5 (5)C28—C29—N8124.1 (6)
C13—C14—Cl1119.9 (5)O12—C29—N8114.2 (6)
O6—C15—H15A109.5O12—C30—H30A109.5
O6—C15—H15B109.5O12—C30—H30B109.5
H15A—C15—H15B109.5H30A—C30—H30B109.5
O6—C15—H15C109.5O12—C30—H30C109.5
H15A—C15—H15C109.5H30A—C30—H30C109.5
H15B—C15—H15C109.5H30B—C30—H30C109.5
O3—S1—N1—C10176.9 (4)O9—S2—N5—C25−58.7 (5)
O4—S1—N1—C10−54.2 (4)O10—S2—N5—C25173.5 (4)
C9—S1—N1—C1061.1 (4)C20—S2—N5—C2557.8 (5)
C3—O1—C2—C1−160.3 (6)C18—O7—C17—C16153.5 (6)
C2—O1—C3—O21.8 (9)C17—O7—C18—O8−3.6 (10)
C2—O1—C3—C4−179.5 (5)C17—O7—C18—C19175.9 (5)
O2—C3—C4—C9−46.4 (9)O8—C18—C19—C24125.1 (7)
O1—C3—C4—C9135.0 (6)O7—C18—C19—C24−54.4 (7)
O2—C3—C4—C5125.9 (7)O8—C18—C19—C20−51.7 (9)
O1—C3—C4—C5−52.6 (7)O7—C18—C19—C20128.8 (6)
C9—C4—C5—C6−2.5 (8)C24—C19—C20—C21−1.0 (8)
C3—C4—C5—C6−175.4 (6)C18—C19—C20—C21175.7 (6)
C4—C5—C6—C74.8 (10)C24—C19—C20—S2176.5 (5)
C5—C6—C7—C8−4.8 (10)C18—C19—C20—S2−6.7 (7)
C6—C7—C8—C92.5 (8)O9—S2—C20—C217.4 (5)
C7—C8—C9—C4−0.4 (8)O10—S2—C20—C21136.8 (5)
C7—C8—C9—S1−175.3 (4)N5—S2—C20—C21−110.4 (5)
C3—C4—C9—C8172.9 (5)O9—S2—C20—C19−170.2 (4)
C5—C4—C9—C80.4 (7)O10—S2—C20—C19−40.8 (5)
C3—C4—C9—S1−12.5 (7)N5—S2—C20—C1972.1 (5)
C5—C4—C9—S1175.0 (4)C19—C20—C21—C22−1.7 (9)
O3—S1—C9—C8142.1 (4)S2—C20—C21—C22−179.3 (5)
O4—S1—C9—C810.0 (4)C20—C21—C22—C232.6 (11)
N1—S1—C9—C8−105.7 (4)C21—C22—C23—C24−0.8 (12)
O3—S1—C9—C4−32.8 (5)C20—C19—C24—C232.7 (9)
O4—S1—C9—C4−164.9 (4)C18—C19—C24—C23−174.3 (6)
N1—S1—C9—C479.4 (4)C22—C23—C24—C19−1.8 (11)
S1—N1—C10—O5−5.1 (7)C26—N6—C25—O11−177.9 (5)
S1—N1—C10—N2176.5 (3)C26—N6—C25—N52.3 (8)
C11—N2—C10—O5179.5 (5)S2—N5—C25—O1110.6 (8)
C11—N2—C10—N1−2.1 (7)S2—N5—C25—N6−169.5 (4)
C12—N3—C11—N4−2.0 (7)C27—N7—C26—N80.6 (8)
C12—N3—C11—N2180.0 (4)C27—N7—C26—N6−176.7 (5)
C14—N4—C11—N32.1 (7)C29—N8—C26—N70.9 (7)
C14—N4—C11—N2−179.8 (4)C29—N8—C26—N6178.2 (4)
C10—N2—C11—N31.8 (7)C25—N6—C26—N7−6.2 (8)
C10—N2—C11—N4−176.4 (4)C25—N6—C26—N8176.3 (5)
C11—N3—C12—O6179.4 (4)C26—N7—C27—C28−1.1 (9)
C11—N3—C12—C130.0 (7)C26—N7—C27—Cl2177.4 (4)
C15—O6—C12—N3−0.7 (8)N7—C27—C28—C290.0 (11)
C15—O6—C12—C13178.6 (6)Cl2—C27—C28—C29−178.3 (5)
N3—C12—C13—C141.6 (8)C27—C28—C29—O12−179.0 (6)
O6—C12—C13—C14−177.8 (5)C27—C28—C29—N81.7 (10)
C11—N4—C14—C13−0.3 (8)C30—O12—C29—C28−180.0 (5)
C11—N4—C14—Cl1178.8 (4)C30—O12—C29—N8−0.6 (7)
C12—C13—C14—N4−1.5 (9)C26—N8—C29—C28−2.1 (8)
C12—C13—C14—Cl1179.5 (4)C26—N8—C29—O12178.6 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N30.861.962.648 (6)136
N2—H2A···O5i0.862.002.831 (8)162
N5—H5B···N70.861.962.651 (6)136
N6—H6B···O2ii0.862.142.973 (7)162
C8—H8A···O40.932.432.821 (6)105
C21—H21A···O90.932.442.848 (8)107
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N30.861.962.648 (6)136
N2—H2A···O5i0.862.002.831 (8)162
N5—H5B···N70.861.962.651 (6)136
N6—H6B···O2ii0.862.142.973 (7)162
C8—H8A···O40.932.432.821 (6)105
C21—H21A···O90.932.442.848 (8)107
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z.
references
References top

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Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

Li, B. & Liu, C. L. (1995). Nongyao, 34, 36–37.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Zhao, J., Yi, G. X., He, S. P., Wang, B. M., Yu, C. X., Li, G., Zhai, Z. X., Li, Z. H. & Li, Q. X. (2006). J. Agric. Food Chem. 54, 4948–4953.