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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 8| August 2008| Pages o1632-o1633

3,3′-Bis(3,4,5-tri­meth­oxy­benzo­yl)-1,1′-(o-phenyl­ene)di­thio­urea ethanol solvate

aInstitute of Natural Products, Research Center for Eco-Environmental Sciences, Guiyang College, Guiyang 550005, People's Republic of China, and bSchool of Chemistry and Environmental Science, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China
*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 24 July 2008; accepted 25 July 2008; online 31 July 2008)

In the mol­ecule of the title compound, C28H30N4O8S2·C2H6O, the benzene ring is oriented at dihedral angles of 38.50 (6) and 5.68 (5)° with respect to the trimethoxy­phenyl rings, while the two trimethoxy­phenyl rings are oriented at a dihedral angle of 44.18 (5)°. Intra­molecular N—H⋯O and N—H⋯S hydrogen bonds result in the formation of non-planar six-, seven- and eight-membered rings. The twisting modes of the two side arms are different [C—N—C—O and C—N—C—N torsion angles = 0.1 (3) and 11.8 (3)°, respectively, in one arm, and 4.6 (3) and −11.5 (3)° in the other]. In the crystal structure, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules.

Related literature

For a related structure, see: Thiam et al. (2008[Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776.]). For ring conformation puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C28H30N4O8S2·C2H6O

  • Mr = 660.75

  • Triclinic, [P \overline 1]

  • a = 7.7619 (15) Å

  • b = 14.473 (3) Å

  • c = 15.810 (3) Å

  • α = 67.113 (10)°

  • β = 73.069 (9)°

  • γ = 78.210 (12)°

  • V = 1556.9 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 113 (2) K

  • 0.14 × 0.12 × 0.10 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.968, Tmax = 0.977

  • 18692 measured reflections

  • 6824 independent reflections

  • 5694 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.115

  • S = 1.07

  • 6824 reflections

  • 433 parameters

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

  • Δρmax = 0.26 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
N4—H4A⋯O1i 0.90 (2) 2.51 (2) 3.403 (2) 173 (2)
N2—H2⋯S1 0.88 (2) 2.69 (2) 3.3527 (19) 133.0 (18)
N2—H2⋯O2 0.88 (2) 1.97 (2) 2.677 (2) 136 (2)
N1—H1⋯O1 0.89 (2) 1.90 (2) 2.621 (2) 137 (2)
N3—H3A⋯O9 0.84 (2) 2.23 (2) 2.949 (2) 145 (2)
O9—H9⋯O2 0.80 (3) 2.13 (3) 2.905 (2) 163 (3)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C1-C6), B (C9-C14) and C (C17-C22) are, of course, planar, and the dihedral angles between them are A/B = 38.50 (6)°, A/C = 5.68 (5)° and B/C = 44.18 (5)°.

The intramolecular N-H···O and N-H···S hydrogen bonds (Table 1) result in the formation of non-planar six-, seven- and eight-membered rings: D (O1/N1/N3/C7/C8/H1), E (O2/N2/N4/C15/C16/H2), F (S1/N1/N2/C1/C2/C7/H2) and G (S1/O2/O9/N3/C7/H2/H3A/H9). Rings D and E adopt flattened-boat [ϕ = 171.38 (2)°, θ = 109.10 (3)° (for ring D) and ϕ = -20.28 (3)°, θ = 96.87 (3)° (for ring E)] conformations, while rings F and G adopt highly twisted conformations having total puckering amplitudes, QT, of 0.160 (3), 0.109 (3), 2.486 (4) and 2.064 (4) Å, respectively (Cremer & Pople, 1975). The two side arms are not twisted in the same way, as evidenced by the torsion angles: C7-N3-C8-O1 [0.1 (3)°], C8-N3-C7-N1 [11.8 (3)°] and C15-N4-C16-O2 [4.6 (3)°], C16-N4-C15-N2 [-11.5 (3)°], as in 1,2-bis(N'-benzoylthioureido)- benzene (Thiam et al., 2008).

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

Related literature top

For related structures, see: Thiam et al. (2008). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, ammonium thiocyanate (30 mmol), 3,4,5-trimethoxylbenzoyl chloride (20 mmol), PEG-400 (0.2 mmol) and acetone (50 mL) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at room temperature for 1 h, then benzene-1,2-diamine (9.5 mmol) was added, and the mixture was stirred for 2 h. The mixture was poured into water (20 ml). The resulting solid was filtered, washed with water, and then dried. Crystals suitable for X-ray analysis were obtained by the recrystallization of the solid residue from a mixture of N,N-dimethyl- formamide/ethanol (1:1) by slow evaporation at room temperature.

Refinement top

H1, H2, H3A, H4A (for NH) and H9 (for OH) atoms were located in difference syntheses and refined isotropically [N-H = 0.84 (2)-0.90 (2) Å and Uiso(H) = 0.026 (6)-0.036 (7) Å2; O-H = 0.80 (3) Å and Uiso(H) = 0.043 Å2]. The remaining H atoms were positioned geometrically, with C-H = 0.95, 0.98 and 0.99 Å for aromatic, methyl and methylene H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (Rigaku/MSC, 2005); 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 molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
3,3'-Bis(3,4,5-trimethoxybenzoyl)-1,1'-(o-phenylene)dithiourea ethanol solvate top
Crystal data top
C28H30N4O8S2·C2H6OZ = 2
Mr = 660.75F(000) = 696
Triclinic, P1Dx = 1.409 Mg m3
Hall symbol: -P 1Melting point: 475 K
a = 7.7619 (15) ÅMo Kα radiation, λ = 0.71070 Å
b = 14.473 (3) ÅCell parameters from 4542 reflections
c = 15.810 (3) Åθ = 2.4–27.2°
α = 67.113 (10)°µ = 0.23 mm1
β = 73.069 (9)°T = 113 K
γ = 78.210 (12)°Block, colorless
V = 1556.9 (5) Å30.14 × 0.12 × 0.10 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
6824 independent reflections
Radiation source: rotating anode5694 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.046
Detector resolution: 14.63 pixels mm-1θmax = 27.2°, θmin = 2.5°
ω scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1818
Tmin = 0.968, Tmax = 0.977l = 2020
18692 measured reflections
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)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4672P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
6824 reflectionsΔρmax = 0.26 e Å3
433 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0140 (12)
Crystal data top
C28H30N4O8S2·C2H6Oγ = 78.210 (12)°
Mr = 660.75V = 1556.9 (5) Å3
Triclinic, P1Z = 2
a = 7.7619 (15) ÅMo Kα radiation
b = 14.473 (3) ŵ = 0.23 mm1
c = 15.810 (3) ÅT = 113 K
α = 67.113 (10)°0.14 × 0.12 × 0.10 mm
β = 73.069 (9)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
6824 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
5694 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.977Rint = 0.046
18692 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.26 e Å3
6824 reflectionsΔρmin = 0.32 e Å3
433 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
S10.47072 (7)0.74462 (4)0.51329 (3)0.02065 (14)
S20.93034 (8)0.44117 (4)0.34131 (4)0.02578 (15)
O11.02467 (19)0.81993 (11)0.48592 (9)0.0250 (3)
O20.6648 (2)0.51201 (10)0.60921 (10)0.0274 (4)
O31.2473 (2)0.92569 (11)0.70183 (10)0.0286 (4)
O41.0727 (2)0.82041 (11)0.87598 (10)0.0278 (4)
O50.7886 (2)0.72356 (11)0.90656 (10)0.0287 (4)
O60.7859 (2)0.27652 (10)0.93150 (10)0.0243 (3)
O70.7307 (2)0.09337 (10)0.94217 (9)0.0244 (3)
O80.6871 (2)0.06352 (10)0.79539 (9)0.0229 (3)
O90.5525 (2)0.62076 (12)0.74010 (11)0.0285 (4)
H90.568 (4)0.582 (2)0.7125 (19)0.043*
N10.8159 (2)0.76073 (12)0.41701 (11)0.0177 (4)
H10.923 (3)0.7772 (17)0.4133 (16)0.030 (7)*
N20.7346 (2)0.57673 (12)0.42050 (12)0.0200 (4)
H20.685 (3)0.5885 (17)0.4737 (17)0.028 (6)*
N30.7451 (2)0.76939 (12)0.56722 (12)0.0184 (4)
H3A0.673 (3)0.7516 (17)0.6201 (17)0.026 (6)*
N40.7865 (2)0.41196 (12)0.52015 (11)0.0198 (4)
H4A0.830 (3)0.3486 (19)0.5237 (17)0.036 (7)*
C10.7839 (3)0.75352 (14)0.33508 (13)0.0175 (4)
C20.7479 (3)0.66254 (14)0.33554 (13)0.0176 (4)
C30.7222 (3)0.65850 (15)0.25351 (14)0.0207 (4)
H30.69110.59810.25390.025*
C40.7419 (3)0.74278 (16)0.17098 (14)0.0238 (5)
H40.72720.73920.11480.029*
C50.7829 (3)0.83206 (16)0.17021 (14)0.0249 (5)
H50.79870.88900.11340.030*
C60.8006 (3)0.83775 (15)0.25285 (14)0.0213 (4)
H60.82420.89950.25320.026*
C70.6875 (3)0.75825 (13)0.49576 (13)0.0167 (4)
C80.9074 (3)0.79901 (14)0.56059 (14)0.0193 (4)
C90.9324 (3)0.80961 (14)0.64638 (14)0.0191 (4)
C101.0706 (3)0.86638 (14)0.63139 (14)0.0199 (4)
H101.13580.90010.56900.024*
C111.1123 (3)0.87340 (15)0.70806 (14)0.0207 (4)
C121.0173 (3)0.82339 (15)0.80012 (14)0.0217 (4)
C130.8750 (3)0.76923 (15)0.81379 (13)0.0215 (4)
C140.8326 (3)0.76151 (15)0.73745 (14)0.0219 (4)
H140.73700.72400.74710.026*
C150.8105 (3)0.48263 (14)0.42749 (14)0.0189 (4)
C160.7225 (3)0.42760 (15)0.60517 (14)0.0197 (4)
C170.7314 (3)0.33652 (14)0.69148 (13)0.0180 (4)
C180.7536 (3)0.35253 (15)0.76900 (14)0.0200 (4)
H180.76620.41820.76470.024*
C190.7570 (3)0.27097 (15)0.85280 (13)0.0193 (4)
C200.7301 (3)0.17510 (14)0.86015 (13)0.0187 (4)
C210.7114 (3)0.16009 (14)0.78097 (14)0.0187 (4)
C220.7134 (3)0.24057 (14)0.69593 (13)0.0172 (4)
H220.70260.23040.64190.021*
C231.3530 (3)0.97237 (17)0.60921 (16)0.0301 (5)
H23A1.41180.92090.58120.045*
H23B1.44551.00690.61270.045*
H23C1.27441.02140.57010.045*
C240.9843 (3)0.89960 (16)0.91201 (15)0.0274 (5)
H24A1.01100.96510.86280.041*
H24B1.02850.89180.96670.041*
H24C0.85320.89580.93110.041*
C250.6375 (3)0.67215 (18)0.92291 (16)0.0349 (6)
H25A0.54740.71920.89030.052*
H25B0.58340.64550.99090.052*
H25C0.67770.61640.89880.052*
C260.8306 (3)0.37088 (16)0.92470 (15)0.0277 (5)
H26A0.93370.39260.87090.042*
H26B0.86240.36290.98290.042*
H26C0.72620.42170.91560.042*
C270.5853 (3)0.09950 (17)1.02149 (16)0.0348 (6)
H27A0.62190.13371.05520.052*
H27B0.55730.03141.06430.052*
H27C0.47770.13760.99890.052*
C280.6740 (3)0.04397 (15)0.71577 (14)0.0249 (5)
H28A0.56840.08490.69290.037*
H28B0.66080.02760.73430.037*
H28C0.78390.06130.66540.037*
C290.3609 (3)0.63770 (18)0.77554 (16)0.0312 (5)
H29A0.29870.65090.72490.037*
H29B0.33430.69830.79370.037*
C300.2880 (4)0.5489 (2)0.85986 (17)0.0428 (7)
H30A0.31030.48930.84160.064*
H30B0.15750.56390.88240.064*
H30C0.34890.53580.91030.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0181 (3)0.0241 (3)0.0211 (3)0.00133 (19)0.0054 (2)0.0093 (2)
S20.0320 (3)0.0201 (3)0.0198 (3)0.0011 (2)0.0011 (2)0.0068 (2)
O10.0240 (8)0.0343 (8)0.0179 (7)0.0081 (6)0.0015 (6)0.0103 (6)
O20.0436 (10)0.0171 (7)0.0200 (8)0.0031 (6)0.0090 (7)0.0070 (6)
O30.0308 (9)0.0363 (9)0.0256 (8)0.0101 (7)0.0086 (7)0.0137 (7)
O40.0350 (9)0.0317 (8)0.0237 (8)0.0064 (6)0.0154 (7)0.0160 (7)
O50.0367 (9)0.0332 (8)0.0156 (7)0.0084 (7)0.0045 (6)0.0069 (6)
O60.0353 (9)0.0211 (7)0.0203 (7)0.0044 (6)0.0106 (6)0.0076 (6)
O70.0329 (9)0.0187 (7)0.0160 (7)0.0021 (6)0.0059 (6)0.0024 (6)
O80.0356 (9)0.0149 (7)0.0202 (7)0.0050 (6)0.0100 (6)0.0046 (6)
O90.0278 (9)0.0318 (9)0.0286 (9)0.0028 (7)0.0046 (7)0.0149 (7)
N10.0187 (9)0.0202 (8)0.0159 (8)0.0019 (6)0.0051 (7)0.0073 (7)
N20.0280 (10)0.0165 (8)0.0142 (8)0.0005 (7)0.0056 (7)0.0045 (7)
N30.0199 (9)0.0227 (9)0.0134 (8)0.0030 (7)0.0032 (7)0.0074 (7)
N40.0268 (10)0.0137 (8)0.0165 (8)0.0013 (7)0.0036 (7)0.0041 (7)
C10.0152 (10)0.0219 (10)0.0155 (9)0.0005 (7)0.0032 (7)0.0084 (8)
C20.0171 (10)0.0183 (9)0.0158 (9)0.0013 (7)0.0035 (8)0.0061 (8)
C30.0218 (11)0.0214 (10)0.0202 (10)0.0017 (8)0.0066 (8)0.0094 (8)
C40.0252 (11)0.0293 (11)0.0184 (10)0.0045 (8)0.0084 (8)0.0112 (9)
C50.0285 (12)0.0248 (11)0.0155 (10)0.0012 (8)0.0048 (9)0.0031 (8)
C60.0229 (11)0.0174 (10)0.0197 (10)0.0010 (8)0.0031 (8)0.0043 (8)
C70.0219 (10)0.0131 (9)0.0151 (9)0.0000 (7)0.0069 (8)0.0039 (7)
C80.0206 (10)0.0176 (9)0.0205 (10)0.0003 (7)0.0067 (8)0.0071 (8)
C90.0209 (10)0.0194 (10)0.0195 (10)0.0019 (8)0.0069 (8)0.0098 (8)
C100.0201 (10)0.0198 (10)0.0190 (10)0.0009 (8)0.0057 (8)0.0066 (8)
C110.0210 (11)0.0215 (10)0.0234 (10)0.0007 (8)0.0072 (8)0.0117 (8)
C120.0263 (11)0.0229 (10)0.0208 (10)0.0051 (8)0.0121 (9)0.0119 (8)
C130.0254 (11)0.0217 (10)0.0151 (10)0.0019 (8)0.0055 (8)0.0056 (8)
C140.0241 (11)0.0213 (10)0.0212 (10)0.0013 (8)0.0063 (8)0.0083 (8)
C150.0197 (10)0.0178 (9)0.0201 (10)0.0032 (7)0.0058 (8)0.0061 (8)
C160.0222 (10)0.0197 (10)0.0180 (10)0.0037 (8)0.0055 (8)0.0063 (8)
C170.0176 (10)0.0189 (10)0.0158 (9)0.0005 (7)0.0034 (8)0.0057 (8)
C180.0217 (10)0.0182 (10)0.0211 (10)0.0023 (7)0.0051 (8)0.0077 (8)
C190.0195 (10)0.0240 (10)0.0150 (9)0.0009 (8)0.0047 (8)0.0077 (8)
C200.0199 (10)0.0173 (9)0.0159 (9)0.0013 (7)0.0047 (8)0.0027 (8)
C210.0176 (10)0.0161 (9)0.0233 (10)0.0024 (7)0.0054 (8)0.0071 (8)
C220.0175 (10)0.0187 (9)0.0149 (9)0.0020 (7)0.0037 (7)0.0051 (8)
C230.0306 (13)0.0312 (12)0.0327 (12)0.0105 (9)0.0052 (10)0.0137 (10)
C240.0357 (13)0.0284 (11)0.0226 (11)0.0013 (9)0.0092 (9)0.0129 (9)
C250.0463 (15)0.0343 (13)0.0222 (11)0.0170 (11)0.0012 (10)0.0083 (10)
C260.0365 (13)0.0264 (11)0.0263 (11)0.0053 (9)0.0096 (10)0.0129 (9)
C270.0348 (13)0.0300 (12)0.0250 (12)0.0045 (10)0.0006 (10)0.0008 (10)
C280.0355 (13)0.0191 (10)0.0235 (11)0.0022 (8)0.0110 (9)0.0086 (9)
C290.0277 (12)0.0373 (13)0.0277 (12)0.0028 (9)0.0076 (10)0.0100 (10)
C300.0557 (17)0.0482 (16)0.0263 (13)0.0224 (13)0.0021 (12)0.0150 (12)
Geometric parameters (Å, º) top
S1—C71.664 (2)C9—C101.393 (3)
S2—C151.659 (2)C9—C141.396 (3)
O1—C81.234 (2)C10—C111.386 (3)
O2—C161.232 (2)C10—H100.9500
O3—C111.373 (2)C11—C121.400 (3)
O3—C231.425 (3)C12—C131.402 (3)
O4—C121.370 (2)C13—C141.389 (3)
O4—C241.438 (2)C14—H140.9500
O5—C131.375 (2)C16—C171.491 (3)
O5—C251.423 (3)C17—C181.395 (3)
O6—C191.361 (2)C17—C221.397 (3)
O6—C261.433 (2)C18—C191.393 (3)
O7—C201.374 (2)C18—H180.9500
O7—C271.441 (3)C19—C201.400 (3)
O8—C211.370 (2)C20—C211.402 (3)
O8—C281.428 (2)C21—C221.393 (3)
O9—C291.434 (3)C22—H220.9500
O9—H90.80 (3)C23—H23A0.9800
N1—C71.342 (2)C23—H23B0.9800
N1—C11.433 (3)C23—H23C0.9800
N1—H10.89 (2)C24—H24A0.9800
N2—C151.344 (3)C24—H24B0.9800
N2—C21.425 (2)C24—H24C0.9800
N2—H20.88 (2)C25—H25A0.9800
N3—C81.375 (3)C25—H25B0.9800
N3—C71.403 (3)C25—H25C0.9800
N3—H3A0.84 (2)C26—H26A0.9800
N4—C161.381 (3)C26—H26B0.9800
N4—C151.407 (2)C26—H26C0.9800
N4—H4A0.90 (2)C27—H27A0.9800
C1—C61.388 (3)C27—H27B0.9800
C1—C21.398 (3)C27—H27C0.9800
C2—C31.393 (3)C28—H28A0.9800
C3—C41.391 (3)C28—H28B0.9800
C3—H30.9500C28—H28C0.9800
C4—C51.387 (3)C29—C301.508 (3)
C4—H40.9500C29—H29A0.9900
C5—C61.388 (3)C29—H29B0.9900
C5—H50.9500C30—H30A0.9800
C6—H60.9500C30—H30B0.9800
C8—C91.493 (3)C30—H30C0.9800
C11—O3—C23116.05 (16)C18—C17—C22121.48 (17)
C12—O4—C24114.05 (15)C18—C17—C16116.36 (18)
C13—O5—C25116.56 (17)C22—C17—C16122.13 (18)
C19—O6—C26117.41 (16)C19—C18—C17119.18 (18)
C20—O7—C27114.85 (15)C19—C18—H18120.4
C21—O8—C28117.05 (15)C17—C18—H18120.4
C29—O9—H9107.2 (19)O6—C19—C18124.44 (18)
C7—N1—C1124.35 (17)O6—C19—C20115.37 (17)
C7—N1—H1116.3 (15)C18—C19—C20120.19 (18)
C1—N1—H1118.6 (15)O7—C20—C19121.59 (18)
C15—N2—C2125.79 (17)O7—C20—C21118.60 (17)
C15—N2—H2117.3 (15)C19—C20—C21119.73 (17)
C2—N2—H2116.3 (15)O8—C21—C22124.37 (18)
C8—N3—C7127.62 (17)O8—C21—C20115.14 (17)
C8—N3—H3A118.5 (16)C22—C21—C20120.47 (18)
C7—N3—H3A113.8 (16)C21—C22—C17118.83 (18)
C16—N4—C15129.46 (17)C21—C22—H22120.6
C16—N4—H4A116.0 (15)C17—C22—H22120.6
C15—N4—H4A114.3 (15)O3—C23—H23A109.5
C6—C1—C2120.34 (18)O3—C23—H23B109.5
C6—C1—N1118.33 (18)H23A—C23—H23B109.5
C2—C1—N1121.21 (17)O3—C23—H23C109.5
C3—C2—C1119.20 (18)H23A—C23—H23C109.5
C3—C2—N2121.58 (18)H23B—C23—H23C109.5
C1—C2—N2119.21 (17)O4—C24—H24A109.5
C4—C3—C2120.1 (2)O4—C24—H24B109.5
C4—C3—H3120.0H24A—C24—H24B109.5
C2—C3—H3120.0O4—C24—H24C109.5
C5—C4—C3120.44 (19)H24A—C24—H24C109.5
C5—C4—H4119.8H24B—C24—H24C109.5
C3—C4—H4119.8O5—C25—H25A109.5
C4—C5—C6119.65 (19)O5—C25—H25B109.5
C4—C5—H5120.2H25A—C25—H25B109.5
C6—C5—H5120.2O5—C25—H25C109.5
C5—C6—C1120.21 (19)H25A—C25—H25C109.5
C5—C6—H6119.9H25B—C25—H25C109.5
C1—C6—H6119.9O6—C26—H26A109.5
N1—C7—N3115.67 (17)O6—C26—H26B109.5
N1—C7—S1125.33 (15)H26A—C26—H26B109.5
N3—C7—S1118.99 (14)O6—C26—H26C109.5
O1—C8—N3121.57 (18)H26A—C26—H26C109.5
O1—C8—C9121.22 (18)H26B—C26—H26C109.5
N3—C8—C9117.16 (17)O7—C27—H27A109.5
C10—C9—C14120.91 (19)O7—C27—H27B109.5
C10—C9—C8115.91 (17)H27A—C27—H27B109.5
C14—C9—C8123.07 (18)O7—C27—H27C109.5
C11—C10—C9119.59 (18)H27A—C27—H27C109.5
C11—C10—H10120.2H27B—C27—H27C109.5
C9—C10—H10120.2O8—C28—H28A109.5
O3—C11—C10124.62 (18)O8—C28—H28B109.5
O3—C11—C12114.95 (18)H28A—C28—H28B109.5
C10—C11—C12120.41 (19)O8—C28—H28C109.5
O4—C12—C11120.25 (19)H28A—C28—H28C109.5
O4—C12—C13120.29 (18)H28B—C28—H28C109.5
C11—C12—C13119.24 (18)O9—C29—C30112.1 (2)
O5—C13—C14124.23 (19)O9—C29—H29A109.2
O5—C13—C12115.03 (18)C30—C29—H29A109.2
C14—C13—C12120.71 (18)O9—C29—H29B109.2
C13—C14—C9119.08 (19)C30—C29—H29B109.2
C13—C14—H14120.5H29A—C29—H29B107.9
C9—C14—H14120.5C29—C30—H30A109.5
N2—C15—N4114.99 (17)C29—C30—H30B109.5
N2—C15—S2128.09 (15)H30A—C30—H30B109.5
N4—C15—S2116.90 (14)C29—C30—H30C109.5
O2—C16—N4121.94 (18)H30A—C30—H30C109.5
O2—C16—C17122.15 (18)H30B—C30—H30C109.5
N4—C16—C17115.90 (17)
C7—N1—C1—C6112.1 (2)C11—C12—C13—O5179.33 (17)
C7—N1—C1—C271.9 (2)O4—C12—C13—C14171.96 (17)
C6—C1—C2—C32.4 (3)C11—C12—C13—C142.6 (3)
N1—C1—C2—C3178.42 (17)O5—C13—C14—C9178.68 (18)
C6—C1—C2—N2178.93 (17)C12—C13—C14—C90.8 (3)
N1—C1—C2—N22.9 (3)C10—C9—C14—C131.2 (3)
C15—N2—C2—C346.2 (3)C8—C9—C14—C13174.92 (18)
C15—N2—C2—C1135.2 (2)C2—N2—C15—N4176.38 (18)
C1—C2—C3—C43.5 (3)C2—N2—C15—S22.4 (3)
N2—C2—C3—C4177.94 (18)C16—N4—C15—N211.5 (3)
C2—C3—C4—C51.6 (3)C16—N4—C15—S2167.45 (17)
C3—C4—C5—C61.3 (3)C15—N4—C16—O24.6 (3)
C4—C5—C6—C12.3 (3)C15—N4—C16—C17174.03 (19)
C2—C1—C6—C50.5 (3)O2—C16—C17—C1828.7 (3)
N1—C1—C6—C5175.64 (18)N4—C16—C17—C18149.99 (18)
C1—N1—C7—N3178.21 (16)O2—C16—C17—C22149.5 (2)
C1—N1—C7—S11.0 (3)N4—C16—C17—C2231.8 (3)
C8—N3—C7—N111.8 (3)C22—C17—C18—C190.3 (3)
C8—N3—C7—S1167.47 (15)C16—C17—C18—C19177.93 (18)
C7—N3—C8—O10.1 (3)C26—O6—C19—C185.4 (3)
C7—N3—C8—C9177.21 (17)C26—O6—C19—C20174.43 (17)
O1—C8—C9—C1015.1 (3)C17—C18—C19—O6176.90 (17)
N3—C8—C9—C10162.03 (17)C17—C18—C19—C202.9 (3)
O1—C8—C9—C14161.21 (19)C27—O7—C20—C1965.1 (3)
N3—C8—C9—C1421.6 (3)C27—O7—C20—C21118.3 (2)
C14—C9—C10—C111.4 (3)O6—C19—C20—O70.9 (3)
C8—C9—C10—C11174.97 (17)C18—C19—C20—O7179.27 (17)
C23—O3—C11—C102.1 (3)O6—C19—C20—C21175.70 (17)
C23—O3—C11—C12176.46 (17)C18—C19—C20—C214.1 (3)
C9—C10—C11—O3178.88 (18)C28—O8—C21—C224.0 (3)
C9—C10—C11—C120.4 (3)C28—O8—C21—C20177.79 (17)
C24—O4—C12—C1193.5 (2)O7—C20—C21—O82.8 (3)
C24—O4—C12—C1392.0 (2)C19—C20—C21—O8179.51 (17)
O3—C11—C12—O46.4 (3)O7—C20—C21—C22178.87 (17)
C10—C11—C12—O4172.17 (17)C19—C20—C21—C222.2 (3)
O3—C11—C12—C13178.98 (17)O8—C21—C22—C17177.19 (17)
C10—C11—C12—C132.4 (3)C20—C21—C22—C171.0 (3)
C25—O5—C13—C145.1 (3)C18—C17—C22—C212.2 (3)
C25—O5—C13—C12176.94 (18)C16—C17—C22—C21175.89 (18)
O4—C12—C13—O56.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.90 (2)2.51 (2)3.403 (2)173 (2)
N2—H2···S10.88 (2)2.69 (2)3.3527 (19)133.0 (18)
N2—H2···O20.88 (2)1.97 (2)2.677 (2)136 (2)
N1—H1···O10.89 (2)1.90 (2)2.621 (2)137 (2)
N3—H3A···O90.84 (2)2.23 (2)2.949 (2)145 (2)
O9—H9···O20.80 (3)2.13 (3)2.905 (2)163 (3)
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC28H30N4O8S2·C2H6O
Mr660.75
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)7.7619 (15), 14.473 (3), 15.810 (3)
α, β, γ (°)67.113 (10), 73.069 (9), 78.210 (12)
V3)1556.9 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.14 × 0.12 × 0.10
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.968, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
18692, 6824, 5694
Rint0.046
(sin θ/λ)max1)0.644
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.115, 1.07
No. of reflections6824
No. of parameters433
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.32

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.90 (2)2.51 (2)3.403 (2)173 (2)
N2—H2···S10.88 (2)2.69 (2)3.3527 (19)133.0 (18)
N2—H2···O20.88 (2)1.97 (2)2.677 (2)136 (2)
N1—H1···O10.89 (2)1.90 (2)2.621 (2)137 (2)
N3—H3A···O90.84 (2)2.23 (2)2.949 (2)145 (2)
O9—H9···O20.80 (3)2.13 (3)2.905 (2)163 (3)
Symmetry code: (i) x+2, y+1, z+1.
 

Acknowledgements

The authors thank Guiyang College for financial support.

References

First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationRigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationThiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 8| August 2008| Pages o1632-o1633
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds