organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Methyl 4-(4-methyl­benzamido)-2-sulfamoylbenzoate

aCollege of Chemistry and Chemical Engineering, The North University for Ethnics, Yinchuan, 750021, People's Republic of China
*Correspondence e-mail: nkulxh@gmail.com

(Received 16 October 2008; accepted 3 November 2008; online 8 November 2008)

The title compound, C16H16N2O5S, is a potent new fungicide. There are two mol­ecules in the asymmetric unit which are linked by C—H⋯π inter­actions, forming a dimer. The two phenyl rings in each mol­ecules are almost coplanar, with C—N—C—C torsion angles of 177.6 (2) and −172.5 (2)°. There are inter­molecular and intra­molecular N—H⋯O hydrogen bonds in the crystal structure.

Related literature

For the preparation and properties of substituted amides, see: Gong et al. (2008[Gong, Y., Barbay, J. K., Buntinx, M., Li, J., Van Wauweb, J., Claes, C., Van Lommen, G., Hornby, P. J. & He, W. (2008). Bioorg. Med. Chem. Lett. 18, 3852-3855.]); Liu et al. (2007a[Liu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007b). Bioorg. Med. Chem. Lett. 17, 3784-3788.],b[Liu, X. H., Chen, P. Q., He, F. Q., Wang, S. H., Song, H. B. & Li, Z. M. (2007a). Struct. Chem. 18, 563-568.]); Wang et al. (2008[Wang, M. Y., Guo, W. C., Lan, F., Li, Y. H. & Li, Z. M. (2008). Chin. J. Org. Chem. 287, 649-656.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O5S

  • Mr = 348.37

  • Triclinic, [P \overline 1]

  • a = 9.1968 (16) Å

  • b = 11.078 (2) Å

  • c = 15.914 (3) Å

  • α = 75.894 (3)°

  • β = 87.124 (3)°

  • γ = 84.123 (3)°

  • V = 1563.7 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 294 (2) K

  • 0.24 × 0.20 × 0.14 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.945, Tmax = 0.968

  • 8144 measured reflections

  • 5479 independent reflections

  • 3677 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.120

  • S = 1.01

  • 5479 reflections

  • 461 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O7i 0.890 (10) 2.414 (15) 3.256 (3) 158 (2)
N2—H2A⋯O8ii 0.888 (10) 2.166 (12) 2.993 (3) 155 (2)
N3—H3A⋯O8iii 0.889 (10) 2.59 (2) 3.254 (3) 132 (2)
N4—H4A⋯O1iii 0.886 (10) 2.088 (11) 2.958 (3) 168 (3)
N2—H2B⋯O4 0.892 (10) 2.149 (18) 2.905 (3) 142 (2)
N4—H4B⋯O9 0.888 (10) 2.10 (2) 2.789 (3) 134 (2)
N4—H4B⋯O6iv 0.888 (10) 2.59 (2) 3.298 (3) 137 (2)
C7—H7ACg1ii 0.96 2.87 3.7491 148 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+2, -z+2; (iv) -x+2, -y+2, -z+2. Cg1 is the centroid of the C17--C22 ring.

Data collection: SMART (Bruker, 2004[Bruker. (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker. (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Amide derivative as a kind of highly bioactive compound has been studied broadly for many years. Whereas numerous references to the preparations and properties of a large variety of substituted amides exist in the literature (Liu et al., 2007a). These compounds had long been used in agriculture (Liu et al., 2007b) and medicine (Gong et al.,2008). In view of these facts and in continuation of our interest in the agriculture, we attempted to synthesize a series of amide derivatives, some of which have comparatively high fungicidal activity.

The molecular structure of title compound is showing in Fig.1. The X-ray analysis reveals that the benzene ring is planar. The carboxamide moiety is coplanar with the benzene ring [dihedral angle -1.5 (4)°]. The crystal structure is stabilized by the formation of inversion related dimers linked by C-H···π interactions (Table 1, Fig. 2).

Related literature top

For the preparation and properties of substituted amides, see: Gong et al. (2008); Liu et al. (2007a,b); Wang et al. (2008).

Experimental top

The title compound was prepared according to the similar reported procedure (Wang, et al., 2008). Dropwised 4-methylbenzoyl chloride (7.5 mmol) to methyl 4-amino-2-sulfamoylbenzoate (7.50 mmol) in THF (20 ml) solution, then refluxed for 4 h. Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from a mixture of ethyl acetate and petroleum ether.

Refinement top

The structure was solved by direct methods and successive Fourier difference synthesis. The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aromatic C—H=0.93Å, aliphatic C—H = 0.97 (2)Å, N—H=0.86Å, Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Partial packing diagram for (I). The dotted lines show the C-H···π interactions and H-bond. H atoms have been omitted for clarity.
[Figure 3] Fig. 3. Reaction scheme.
methyl 4-(4-methylbenzamido)-2-sulfamoylbenzoate top
Crystal data top
C16H16N2O5SZ = 4
Mr = 348.37F(000) = 728
Triclinic, P1Dx = 1.480 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1968 (16) ÅCell parameters from 2452 reflections
b = 11.078 (2) Åθ = 2.6–25.9°
c = 15.914 (3) ŵ = 0.24 mm1
α = 75.894 (3)°T = 294 K
β = 87.124 (3)°Clubbed, colorless
γ = 84.123 (3)°0.24 × 0.20 × 0.14 mm
V = 1563.7 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
5479 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
phi and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 108
Tmin = 0.945, Tmax = 0.968k = 1310
8144 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.5359P]
where P = (Fo2 + 2Fc2)/3
5479 reflections(Δ/σ)max = 0.003
461 parametersΔρmax = 0.22 e Å3
8 restraintsΔρmin = 0.32 e Å3
Crystal data top
C16H16N2O5Sγ = 84.123 (3)°
Mr = 348.37V = 1563.7 (5) Å3
Triclinic, P1Z = 4
a = 9.1968 (16) ÅMo Kα radiation
b = 11.078 (2) ŵ = 0.24 mm1
c = 15.914 (3) ÅT = 294 K
α = 75.894 (3)°0.24 × 0.20 × 0.14 mm
β = 87.124 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5479 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3677 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.968Rint = 0.023
8144 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0428 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.22 e Å3
5479 reflectionsΔρmin = 0.32 e Å3
461 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
xyzUiso*/Ueq
S10.48593 (7)0.28763 (6)0.70812 (4)0.0363 (2)
S20.64701 (7)1.09651 (6)1.08377 (4)0.03159 (18)
O10.1820 (2)0.58510 (18)1.01610 (12)0.0516 (6)
O20.59114 (19)0.21940 (18)0.76916 (12)0.0465 (5)
O30.5328 (2)0.36685 (19)0.62914 (12)0.0530 (6)
O40.2127 (2)0.40235 (19)0.58979 (12)0.0556 (6)
O50.1961 (2)0.60599 (18)0.58636 (12)0.0495 (5)
O60.9616 (2)0.79515 (19)0.78099 (12)0.0543 (6)
O70.55730 (19)1.17378 (17)1.01674 (11)0.0404 (5)
O80.57554 (19)1.02353 (17)1.15791 (11)0.0431 (5)
O90.8735 (2)0.96320 (19)1.21207 (12)0.0518 (6)
O100.9933 (2)0.78427 (19)1.20227 (12)0.0571 (6)
N10.3212 (3)0.4194 (2)0.98482 (14)0.0377 (6)
N20.3947 (3)0.1860 (2)0.68291 (16)0.0423 (6)
N30.7773 (2)0.9255 (2)0.81909 (14)0.0393 (6)
N40.7427 (2)1.1888 (2)1.11465 (16)0.0376 (6)
C10.3070 (3)0.4445 (2)1.13223 (16)0.0325 (6)
C20.2253 (3)0.4934 (3)1.19400 (18)0.0480 (8)
H20.14690.55301.17700.058*
C30.2596 (3)0.4544 (3)1.28001 (18)0.0522 (8)
H30.20230.48761.32030.063*
C40.3756 (3)0.3677 (3)1.30870 (17)0.0410 (7)
C50.4579 (3)0.3219 (3)1.24656 (19)0.0533 (8)
H50.53860.26461.26330.064*
C60.4239 (3)0.3587 (3)1.16056 (18)0.0485 (8)
H60.48110.32491.12050.058*
C70.4133 (4)0.3275 (3)1.40279 (18)0.0558 (9)
H7A0.39400.24191.42530.084*
H7B0.35510.37931.43450.084*
H7C0.51500.33541.40870.084*
C80.2647 (3)0.4900 (2)1.04024 (16)0.0340 (6)
C90.2944 (3)0.4394 (2)0.89600 (16)0.0324 (6)
C100.3841 (3)0.3679 (2)0.84935 (16)0.0334 (6)
H100.45780.31060.87730.040*
C110.3642 (3)0.3814 (2)0.76245 (16)0.0312 (6)
C120.2557 (3)0.4688 (2)0.71804 (16)0.0345 (6)
C130.1686 (3)0.5392 (3)0.76606 (17)0.0407 (7)
H130.09700.59870.73790.049*
C140.1844 (3)0.5242 (3)0.85342 (17)0.0400 (7)
H140.12180.57060.88390.048*
C150.2222 (3)0.4858 (3)0.62516 (17)0.0380 (7)
C160.1575 (4)0.6338 (3)0.49659 (19)0.0649 (10)
H16A0.23360.59780.46420.097*
H16B0.14550.72270.47400.097*
H16C0.06750.59930.49180.097*
C170.8123 (3)0.9163 (3)0.66853 (17)0.0359 (6)
C180.7012 (3)1.0074 (3)0.63916 (19)0.0544 (9)
H180.64321.04070.67910.065*
C190.6733 (3)1.0506 (3)0.55252 (19)0.0556 (9)
H190.59801.11320.53530.067*
C200.7543 (3)1.0035 (3)0.49037 (18)0.0427 (7)
C210.8621 (4)0.9087 (3)0.51993 (19)0.0571 (9)
H210.91660.87270.48000.069*
C220.8920 (3)0.8655 (3)0.60655 (18)0.0509 (8)
H220.96610.80170.62390.061*
C230.7282 (4)1.0553 (3)0.39532 (18)0.0587 (9)
H23A0.63041.04310.38290.088*
H23B0.79671.01280.36230.088*
H23C0.74081.14300.38010.088*
C240.8570 (3)0.8714 (3)0.76026 (17)0.0356 (6)
C250.8069 (3)0.9098 (2)0.90663 (16)0.0318 (6)
C260.7350 (3)0.9965 (2)0.94941 (16)0.0318 (6)
H260.66921.05990.91950.038*
C270.7607 (3)0.9889 (2)1.03508 (15)0.0283 (6)
C280.8636 (3)0.8951 (2)1.08109 (16)0.0309 (6)
C290.9298 (3)0.8095 (2)1.03729 (17)0.0360 (6)
H290.99630.74611.06650.043*
C300.9014 (3)0.8142 (2)0.95255 (16)0.0355 (6)
H300.94570.75310.92620.043*
C310.9073 (3)0.8870 (2)1.17093 (16)0.0329 (6)
C321.0496 (3)0.7699 (3)1.28726 (18)0.0553 (9)
H32A1.07170.84981.29420.083*
H32B1.13690.71341.29400.083*
H32C0.97770.73711.33030.083*
H1A0.382 (3)0.3537 (18)1.0090 (17)0.056 (9)*
H2A0.374 (3)0.1235 (19)0.7272 (12)0.051 (9)*
H2B0.319 (2)0.222 (2)0.6504 (14)0.059 (10)*
H3A0.700 (2)0.979 (2)0.8004 (17)0.055 (9)*
H4A0.775 (3)1.2487 (19)1.0724 (12)0.051 (9)*
H4B0.806 (2)1.151 (2)1.1556 (13)0.062 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0364 (4)0.0364 (4)0.0364 (4)0.0022 (3)0.0045 (3)0.0123 (3)
S20.0301 (4)0.0323 (4)0.0305 (4)0.0073 (3)0.0017 (3)0.0079 (3)
O10.0721 (14)0.0415 (12)0.0356 (11)0.0238 (11)0.0059 (10)0.0095 (9)
O20.0377 (11)0.0493 (12)0.0521 (12)0.0131 (9)0.0062 (9)0.0173 (10)
O30.0604 (13)0.0513 (13)0.0464 (12)0.0103 (11)0.0193 (10)0.0120 (10)
O40.0787 (16)0.0478 (13)0.0415 (12)0.0046 (12)0.0141 (11)0.0149 (10)
O50.0683 (14)0.0400 (12)0.0349 (11)0.0076 (10)0.0095 (10)0.0024 (9)
O60.0574 (13)0.0596 (14)0.0436 (12)0.0261 (11)0.0084 (10)0.0197 (11)
O70.0395 (11)0.0411 (11)0.0379 (11)0.0156 (9)0.0102 (8)0.0101 (9)
O80.0397 (11)0.0453 (12)0.0382 (11)0.0025 (9)0.0088 (9)0.0030 (9)
O90.0670 (14)0.0497 (13)0.0380 (11)0.0193 (11)0.0147 (10)0.0166 (10)
O100.0750 (15)0.0503 (13)0.0406 (12)0.0300 (12)0.0232 (11)0.0106 (10)
N10.0463 (14)0.0334 (13)0.0311 (13)0.0108 (11)0.0048 (10)0.0087 (10)
N20.0500 (16)0.0340 (14)0.0429 (15)0.0016 (12)0.0002 (13)0.0115 (12)
N30.0349 (13)0.0495 (15)0.0336 (13)0.0132 (12)0.0062 (10)0.0162 (11)
N40.0408 (14)0.0331 (14)0.0387 (14)0.0032 (11)0.0059 (12)0.0099 (11)
C10.0370 (15)0.0282 (14)0.0319 (14)0.0013 (12)0.0018 (12)0.0070 (11)
C20.0487 (18)0.0529 (19)0.0390 (17)0.0212 (15)0.0050 (14)0.0144 (14)
C30.064 (2)0.057 (2)0.0338 (16)0.0158 (17)0.0003 (14)0.0156 (14)
C40.0524 (18)0.0353 (16)0.0341 (15)0.0038 (14)0.0037 (13)0.0057 (13)
C50.059 (2)0.0521 (19)0.0432 (18)0.0233 (16)0.0097 (15)0.0095 (15)
C60.0571 (19)0.0495 (18)0.0363 (16)0.0185 (15)0.0016 (14)0.0150 (14)
C70.074 (2)0.052 (2)0.0383 (17)0.0018 (17)0.0105 (16)0.0059 (15)
C80.0386 (15)0.0307 (15)0.0325 (14)0.0015 (13)0.0013 (12)0.0084 (12)
C90.0374 (15)0.0290 (14)0.0307 (14)0.0010 (12)0.0008 (12)0.0081 (11)
C100.0351 (15)0.0279 (14)0.0361 (15)0.0014 (12)0.0022 (12)0.0073 (12)
C110.0325 (14)0.0285 (14)0.0325 (14)0.0000 (12)0.0002 (11)0.0086 (11)
C120.0388 (15)0.0324 (15)0.0316 (14)0.0004 (12)0.0036 (12)0.0071 (12)
C130.0416 (16)0.0408 (17)0.0379 (16)0.0123 (13)0.0122 (13)0.0106 (13)
C140.0426 (17)0.0390 (16)0.0394 (16)0.0094 (13)0.0034 (13)0.0161 (13)
C150.0367 (16)0.0418 (17)0.0330 (15)0.0038 (13)0.0025 (12)0.0070 (13)
C160.086 (3)0.065 (2)0.0357 (18)0.008 (2)0.0110 (17)0.0007 (16)
C170.0353 (15)0.0380 (16)0.0372 (15)0.0008 (13)0.0023 (12)0.0156 (12)
C180.059 (2)0.066 (2)0.0393 (17)0.0270 (17)0.0078 (15)0.0258 (16)
C190.058 (2)0.061 (2)0.0457 (19)0.0245 (17)0.0130 (15)0.0193 (16)
C200.0486 (18)0.0449 (17)0.0388 (16)0.0052 (15)0.0019 (13)0.0175 (14)
C210.069 (2)0.063 (2)0.0392 (18)0.0207 (18)0.0022 (15)0.0224 (16)
C220.0561 (19)0.0534 (19)0.0408 (17)0.0197 (16)0.0012 (14)0.0171 (15)
C230.074 (2)0.064 (2)0.0374 (17)0.0037 (19)0.0082 (16)0.0148 (16)
C240.0330 (15)0.0386 (16)0.0371 (15)0.0042 (13)0.0043 (12)0.0154 (13)
C250.0278 (14)0.0353 (15)0.0339 (14)0.0016 (12)0.0014 (11)0.0121 (12)
C260.0270 (14)0.0320 (15)0.0344 (15)0.0048 (11)0.0037 (11)0.0066 (12)
C270.0279 (13)0.0247 (13)0.0309 (14)0.0005 (11)0.0008 (11)0.0049 (11)
C280.0295 (14)0.0308 (14)0.0308 (14)0.0002 (12)0.0002 (11)0.0050 (11)
C290.0356 (15)0.0324 (15)0.0365 (15)0.0080 (13)0.0046 (12)0.0051 (12)
C300.0361 (15)0.0345 (15)0.0353 (15)0.0058 (12)0.0001 (12)0.0110 (12)
C310.0287 (14)0.0359 (16)0.0310 (14)0.0011 (12)0.0008 (11)0.0030 (12)
C320.062 (2)0.060 (2)0.0378 (17)0.0126 (17)0.0176 (15)0.0043 (15)
Geometric parameters (Å, º) top
S1—O31.422 (2)C9—C141.388 (3)
S1—O21.4275 (19)C9—C101.397 (3)
S1—N21.606 (2)C10—C111.374 (3)
S1—C111.784 (2)C10—H100.9300
S2—O81.4296 (19)C11—C121.405 (3)
S2—O71.4318 (17)C12—C131.391 (4)
S2—N41.592 (2)C12—C151.488 (4)
S2—C271.797 (2)C13—C141.373 (3)
O1—C81.226 (3)C13—H130.9300
O4—C151.206 (3)C14—H140.9300
O5—C151.327 (3)C16—H16A0.9600
O5—C161.441 (3)C16—H16B0.9600
O6—C241.216 (3)C16—H16C0.9600
O9—C311.197 (3)C17—C181.374 (4)
O10—C311.322 (3)C17—C221.393 (4)
O10—C321.439 (3)C17—C241.487 (4)
N1—C81.366 (3)C18—C191.373 (4)
N1—C91.407 (3)C18—H180.9300
N1—H1A0.890 (10)C19—C201.379 (4)
N2—H2A0.888 (10)C19—H190.9300
N2—H2B0.892 (10)C20—C211.379 (4)
N3—C241.374 (3)C20—C231.503 (4)
N3—C251.398 (3)C21—C221.376 (4)
N3—H3A0.889 (10)C21—H210.9300
N4—H4A0.886 (10)C22—H220.9300
N4—H4B0.888 (10)C23—H23A0.9600
C1—C61.376 (4)C23—H23B0.9600
C1—C21.387 (3)C23—H23C0.9600
C1—C81.485 (3)C25—C301.382 (3)
C2—C31.373 (4)C25—C261.402 (3)
C2—H20.9300C26—C271.376 (3)
C3—C41.376 (4)C26—H260.9300
C3—H30.9300C27—C281.417 (3)
C4—C51.379 (4)C28—C291.384 (3)
C4—C71.502 (4)C28—C311.484 (3)
C5—C61.372 (4)C29—C301.374 (3)
C5—H50.9300C29—H290.9300
C6—H60.9300C30—H300.9300
C7—H7A0.9600C32—H32A0.9600
C7—H7B0.9600C32—H32B0.9600
C7—H7C0.9600C32—H32C0.9600
O3—S1—O2119.98 (13)C12—C13—H13118.8
O3—S1—N2106.99 (13)C13—C14—C9119.7 (2)
O2—S1—N2106.49 (13)C13—C14—H14120.2
O3—S1—C11107.35 (12)C9—C14—H14120.2
O2—S1—C11107.47 (11)O4—C15—O5123.6 (2)
N2—S1—C11108.08 (12)O4—C15—C12125.2 (3)
O8—S2—O7117.81 (11)O5—C15—C12111.1 (2)
O8—S2—N4108.82 (12)O5—C16—H16A109.5
O7—S2—N4105.66 (12)O5—C16—H16B109.5
O8—S2—C27106.89 (11)H16A—C16—H16B109.5
O7—S2—C27106.71 (11)O5—C16—H16C109.5
N4—S2—C27110.93 (12)H16A—C16—H16C109.5
C15—O5—C16116.1 (2)H16B—C16—H16C109.5
C31—O10—C32117.0 (2)C18—C17—C22116.9 (3)
C8—N1—C9127.6 (2)C18—C17—C24125.2 (2)
C8—N1—H1A114.6 (19)C22—C17—C24117.8 (2)
C9—N1—H1A117.9 (19)C19—C18—C17121.9 (3)
S1—N2—H2A114.3 (18)C19—C18—H18119.1
S1—N2—H2B111.7 (18)C17—C18—H18119.1
H2A—N2—H2B114.7 (16)C18—C19—C20121.7 (3)
C24—N3—C25127.0 (2)C18—C19—H19119.2
C24—N3—H3A118.2 (19)C20—C19—H19119.2
C25—N3—H3A114.8 (19)C21—C20—C19116.5 (3)
S2—N4—H4A114.9 (17)C21—C20—C23121.9 (3)
S2—N4—H4B114.4 (18)C19—C20—C23121.5 (3)
H4A—N4—H4B116.4 (16)C22—C21—C20122.3 (3)
C6—C1—C2117.4 (2)C22—C21—H21118.9
C6—C1—C8124.5 (2)C20—C21—H21118.9
C2—C1—C8118.1 (2)C21—C22—C17120.6 (3)
C3—C2—C1120.5 (3)C21—C22—H22119.7
C3—C2—H2119.7C17—C22—H22119.7
C1—C2—H2119.7C20—C23—H23A109.5
C2—C3—C4122.3 (3)C20—C23—H23B109.5
C2—C3—H3118.9H23A—C23—H23B109.5
C4—C3—H3118.9C20—C23—H23C109.5
C3—C4—C5116.7 (3)H23A—C23—H23C109.5
C3—C4—C7121.8 (3)H23B—C23—H23C109.5
C5—C4—C7121.5 (3)O6—C24—N3122.3 (2)
C6—C5—C4121.6 (3)O6—C24—C17121.7 (2)
C6—C5—H5119.2N3—C24—C17116.0 (2)
C4—C5—H5119.2C30—C25—N3123.7 (2)
C5—C6—C1121.5 (3)C30—C25—C26118.9 (2)
C5—C6—H6119.3N3—C25—C26117.3 (2)
C1—C6—H6119.3C27—C26—C25120.8 (2)
C4—C7—H7A109.5C27—C26—H26119.6
C4—C7—H7B109.5C25—C26—H26119.6
H7A—C7—H7B109.5C26—C27—C28120.5 (2)
C4—C7—H7C109.5C26—C27—S2115.51 (18)
H7A—C7—H7C109.5C28—C27—S2123.87 (18)
H7B—C7—H7C109.5C29—C28—C27117.0 (2)
O1—C8—N1122.2 (2)C29—C28—C31119.0 (2)
O1—C8—C1121.4 (2)C27—C28—C31123.9 (2)
N1—C8—C1116.4 (2)C30—C29—C28122.8 (2)
C14—C9—C10119.1 (2)C30—C29—H29118.6
C14—C9—N1123.9 (2)C28—C29—H29118.6
C10—C9—N1117.0 (2)C29—C30—C25119.8 (2)
C11—C10—C9120.5 (2)C29—C30—H30120.1
C11—C10—H10119.7C25—C30—H30120.1
C9—C10—H10119.7O9—C31—O10121.9 (2)
C10—C11—C12121.0 (2)O9—C31—C28126.0 (2)
C10—C11—S1117.22 (19)O10—C31—C28112.1 (2)
C12—C11—S1121.70 (19)O10—C32—H32A109.5
C13—C12—C11117.1 (2)O10—C32—H32B109.5
C13—C12—C15118.1 (2)H32A—C32—H32B109.5
C11—C12—C15124.7 (2)O10—C32—H32C109.5
C14—C13—C12122.5 (2)H32A—C32—H32C109.5
C14—C13—H13118.8H32B—C32—H32C109.5
C6—C1—C2—C31.4 (5)C22—C17—C18—C192.7 (5)
C8—C1—C2—C3179.8 (3)C24—C17—C18—C19175.1 (3)
C1—C2—C3—C40.9 (5)C17—C18—C19—C200.9 (5)
C2—C3—C4—C50.5 (5)C18—C19—C20—C211.6 (5)
C2—C3—C4—C7179.0 (3)C18—C19—C20—C23177.0 (3)
C3—C4—C5—C61.4 (5)C19—C20—C21—C222.2 (5)
C7—C4—C5—C6179.8 (3)C23—C20—C21—C22176.4 (3)
C4—C5—C6—C10.9 (5)C20—C21—C22—C170.4 (5)
C2—C1—C6—C50.5 (5)C18—C17—C22—C212.1 (5)
C8—C1—C6—C5179.2 (3)C24—C17—C22—C21175.9 (3)
C9—N1—C8—O11.5 (4)C25—N3—C24—O64.5 (5)
C9—N1—C8—C1177.6 (2)C25—N3—C24—C17172.5 (2)
C6—C1—C8—O1163.4 (3)C18—C17—C24—O6175.9 (3)
C2—C1—C8—O115.2 (4)C22—C17—C24—O61.8 (4)
C6—C1—C8—N117.4 (4)C18—C17—C24—N31.1 (4)
C2—C1—C8—N1164.0 (3)C22—C17—C24—N3178.8 (3)
C8—N1—C9—C1411.7 (4)C24—N3—C25—C3016.3 (4)
C8—N1—C9—C10169.0 (3)C24—N3—C25—C26164.2 (3)
C14—C9—C10—C110.2 (4)C30—C25—C26—C271.8 (4)
N1—C9—C10—C11179.6 (2)N3—C25—C26—C27178.7 (2)
C9—C10—C11—C121.3 (4)C25—C26—C27—C281.7 (4)
C9—C10—C11—S1179.0 (2)C25—C26—C27—S2173.9 (2)
O3—S1—C11—C10134.1 (2)O8—S2—C27—C26123.5 (2)
O2—S1—C11—C103.8 (3)O7—S2—C27—C263.4 (2)
N2—S1—C11—C10110.8 (2)N4—S2—C27—C26118.0 (2)
O3—S1—C11—C1243.6 (3)O8—S2—C27—C2852.0 (2)
O2—S1—C11—C12174.0 (2)O7—S2—C27—C28178.9 (2)
N2—S1—C11—C1271.5 (2)N4—S2—C27—C2866.5 (2)
C10—C11—C12—C130.9 (4)C26—C27—C28—C293.2 (4)
S1—C11—C12—C13178.6 (2)S2—C27—C28—C29172.1 (2)
C10—C11—C12—C15177.1 (3)C26—C27—C28—C31174.4 (2)
S1—C11—C12—C155.2 (4)S2—C27—C28—C3110.2 (4)
C11—C12—C13—C141.0 (4)C27—C28—C29—C301.2 (4)
C15—C12—C13—C14175.5 (3)C31—C28—C29—C30176.5 (2)
C12—C13—C14—C92.5 (4)C28—C29—C30—C252.3 (4)
C10—C9—C14—C132.1 (4)N3—C25—C30—C29176.7 (3)
N1—C9—C14—C13178.6 (3)C26—C25—C30—C293.7 (4)
C16—O5—C15—O41.3 (4)C32—O10—C31—O92.3 (4)
C16—O5—C15—C12178.0 (2)C32—O10—C31—C28176.5 (2)
C13—C12—C15—O4132.5 (3)C29—C28—C31—O9169.9 (3)
C11—C12—C15—O443.7 (4)C27—C28—C31—O97.7 (4)
C13—C12—C15—O544.2 (4)C29—C28—C31—O108.9 (4)
C11—C12—C15—O5139.6 (3)C27—C28—C31—O10173.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O7i0.89 (1)2.41 (2)3.256 (3)158 (2)
N2—H2A···O8ii0.89 (1)2.17 (1)2.993 (3)155 (2)
N3—H3A···O8iii0.89 (1)2.59 (2)3.254 (3)132 (2)
N4—H4A···O1iii0.89 (1)2.09 (1)2.958 (3)168 (3)
N2—H2B···O40.89 (1)2.15 (2)2.905 (3)142 (2)
N4—H4B···O90.89 (1)2.10 (2)2.789 (3)134 (2)
N4—H4B···O6iv0.89 (1)2.59 (2)3.298 (3)137 (2)
C7—H7A···Cg1ii0.962.873.7491148 (2)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+2; (iii) x+1, y+2, z+2; (iv) x+2, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC16H16N2O5S
Mr348.37
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.1968 (16), 11.078 (2), 15.914 (3)
α, β, γ (°)75.894 (3), 87.124 (3), 84.123 (3)
V3)1563.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.24 × 0.20 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.945, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
8144, 5479, 3677
Rint0.023
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.120, 1.02
No. of reflections5479
No. of parameters461
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.32

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O7i0.890 (10)2.414 (15)3.256 (3)158 (2)
N2—H2A···O8ii0.888 (10)2.166 (12)2.993 (3)155 (2)
N3—H3A···O8iii0.889 (10)2.59 (2)3.254 (3)132 (2)
N4—H4A···O1iii0.886 (10)2.088 (11)2.958 (3)168 (3)
N2—H2B···O40.892 (10)2.149 (18)2.905 (3)142 (2)
N4—H4B···O90.888 (10)2.10 (2)2.789 (3)134 (2)
N4—H4B···O6iv0.888 (10)2.59 (2)3.298 (3)137 (2)
C7—H7A···Cg1ii0.962.8663.7491148 (2)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+2; (iii) x+1, y+2, z+2; (iv) x+2, y+2, z+2.
 

References

First citationBruker. (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGong, Y., Barbay, J. K., Buntinx, M., Li, J., Van Wauweb, J., Claes, C., Van Lommen, G., Hornby, P. J. & He, W. (2008). Bioorg. Med. Chem. Lett. 18, 3852–3855.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLiu, X. H., Chen, P. Q., He, F. Q., Wang, S. H., Song, H. B. & Li, Z. M. (2007a). Struct. Chem. 18, 563–568.  Web of Science CSD CrossRef CAS Google Scholar
First citationLiu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007b). Bioorg. Med. Chem. Lett. 17, 3784–3788.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, M. Y., Guo, W. C., Lan, F., Li, Y. H. & Li, Z. M. (2008). Chin. J. Org. Chem. 287, 649–656.  Web of Science CrossRef Google Scholar

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