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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2296.
Published online 2008 November 8. doi:  10.1107/S160053680803599X
PMCID: PMC2959991

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

Abstract

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 [triangle]); Liu et al. (2007a [triangle],b [triangle]); Wang et al. (2008 [triangle]).

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Object name is e-64-o2296-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O5S
  • M r = 348.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2296-efi1.jpg
  • 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 [triangle]) T min = 0.945, T max = 0.968
  • 8144 measured reflections
  • 5479 independent reflections
  • 3677 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 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

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks 070704Bc, I. DOI: 10.1107/S160053680803599X/bq2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803599X/bq2101Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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

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)].

Figures

Fig. 1.
The structure of (I) with displacement ellipsoids drawn at the 30% probability level.
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.
Fig. 3.
Reaction scheme.

Crystal data

C16H16N2O5SZ = 4
Mr = 348.37F000 = 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 = 2.6–25.9º
c = 15.914 (3) ŵ = 0.24 mm1
α = 75.894 (3)ºT = 294 (2) K
β = 87.124 (3)ºClubbed, colorless
γ = 84.123 (3)º0.24 × 0.20 × 0.14 mm
V = 1563.7 (5) Å3

Data collection

Bruker SMART CCD area-detector diffractometer5479 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 294(2) Kθmax = 25.0º
phi and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→8
Tmin = 0.945, Tmax = 0.968k = −13→10
8144 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120  w = 1/[σ2(Fo2) + (0.0551P)2 + 0.5359P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.003
5479 reflectionsΔρmax = 0.22 e Å3
461 parametersΔρmin = −0.32 e Å3
8 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

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)

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, °)

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—C3−1.4 (5)C22—C17—C18—C19−2.7 (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—C23−177.0 (3)
C3—C4—C5—C6−1.4 (5)C19—C20—C21—C22−2.2 (5)
C7—C4—C5—C6−179.8 (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—C21−175.9 (3)
C9—N1—C8—O1−1.5 (4)C25—N3—C24—O64.5 (5)
C9—N1—C8—C1177.6 (2)C25—N3—C24—C17−172.5 (2)
C6—C1—C8—O1−163.4 (3)C18—C17—C24—O6−175.9 (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—N1−164.0 (3)C22—C17—C24—N3178.8 (3)
C8—N1—C9—C14−11.7 (4)C24—N3—C25—C30−16.3 (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—C27−178.7 (2)
C9—C10—C11—C121.3 (4)C25—C26—C27—C281.7 (4)
C9—C10—C11—S1179.0 (2)C25—C26—C27—S2−173.9 (2)
O3—S1—C11—C10−134.1 (2)O8—S2—C27—C26123.5 (2)
O2—S1—C11—C10−3.8 (3)O7—S2—C27—C26−3.4 (2)
N2—S1—C11—C10110.8 (2)N4—S2—C27—C26−118.0 (2)
O3—S1—C11—C1243.6 (3)O8—S2—C27—C28−52.0 (2)
O2—S1—C11—C12174.0 (2)O7—S2—C27—C28−178.9 (2)
N2—S1—C11—C12−71.5 (2)N4—S2—C27—C2866.5 (2)
C10—C11—C12—C13−0.9 (4)C26—C27—C28—C29−3.2 (4)
S1—C11—C12—C13−178.6 (2)S2—C27—C28—C29172.1 (2)
C10—C11—C12—C15−177.1 (3)C26—C27—C28—C31174.4 (2)
S1—C11—C12—C155.2 (4)S2—C27—C28—C31−10.2 (4)
C11—C12—C13—C14−1.0 (4)C27—C28—C29—C301.2 (4)
C15—C12—C13—C14175.5 (3)C31—C28—C29—C30−176.5 (2)
C12—C13—C14—C92.5 (4)C28—C29—C30—C252.3 (4)
C10—C9—C14—C13−2.1 (4)N3—C25—C30—C29176.7 (3)
N1—C9—C14—C13178.6 (3)C26—C25—C30—C29−3.7 (4)
C16—O5—C15—O4−1.3 (4)C32—O10—C31—O9−2.3 (4)
C16—O5—C15—C12−178.0 (2)C32—O10—C31—C28176.5 (2)
C13—C12—C15—O4−132.5 (3)C29—C28—C31—O9169.9 (3)
C11—C12—C15—O443.7 (4)C27—C28—C31—O9−7.7 (4)
C13—C12—C15—O544.2 (4)C29—C28—C31—O10−8.9 (4)
C11—C12—C15—O5−139.6 (3)C27—C28—C31—O10173.6 (2)

Hydrogen-bond geometry (Å, °)

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···Cg1ii0.962.873.7491148 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2101).

References

  • Bruker. (2004). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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. [PubMed]
  • Liu, X. H., Chen, P. Q., He, F. Q., Wang, S. H., Song, H. B. & Li, Z. M. (2007a). Struct. Chem.18, 563–568.
  • 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. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, M. Y., Guo, W. C., Lan, F., Li, Y. H. & Li, Z. M. (2008). Chin. J. Org. Chem.287, 649–656.

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