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

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COMMUNICATIONS
ISSN: 2056-9890

(E)-N′-[2-(4-Chloro-3-nitro­phenyl­sulfon­yl­oxy)-3-meth­oxy­benzyl­­idene]isonicotinohydrazide acetic acid tetra­solvate

aCollege of Chemistry & Environmental Science, Hebei University, Baoding 071002, People's Republic of China, and bCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
*Correspondence e-mail: li_xiaoliu99@163.com

(Received 7 October 2008; accepted 18 October 2008; online 22 October 2008)

In the title compound, C20H15ClN4O7S·4CH3COOH, the central o-vanillin group makes dihedral angles of 9.50 (11) and 42.86 (7)°, respectively, with its attached pyridine and nitro­benzene rings. The crystal packing is stabilized by N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds and C—H⋯O inter­actions, leading to an infinite three-dimensional network. A short intramolecular C—H⋯O contact is also seen.

Related literature

For general background, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Jones et al. (1979[Jones, R. D., Summerville, D. A. & Basolo, F. (1979). Chem. Rev. 17, 139-179.]); Larson & Pecoraro, (1991[Larson, E. J. & Pecoraro, V. L. (1991). J. Am. Chem. Soc. 113, 3810-3818.]); Santos et al. (2001[Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15ClN4O7S·4C2H4O2

  • Mr = 731.09

  • Triclinic, [P \overline 1]

  • a = 8.0565 (16) Å

  • b = 13.876 (3) Å

  • c = 16.097 (3) Å

  • α = 79.01 (3)°

  • β = 76.01 (3)°

  • γ = 75.44 (3)°

  • V = 1673.8 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 294 (2) K

  • 0.23 × 0.18 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.913, Tmax = 0.970

  • 9794 measured reflections

  • 5882 independent reflections

  • 4448 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.146

  • S = 1.01

  • 5882 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O71—H71⋯N11i 0.82 1.84 2.661 (3) 176
C35—H35⋯O17ii 0.93 2.51 3.360 (3) 152
O41—H41⋯O17iii 0.82 1.96 2.698 (3) 150
O41—H41⋯N27iii 0.82 2.59 3.211 (3) 134
N17—H17⋯O42iv 0.86 2.10 2.875 (3) 150
C27—H27⋯O42iv 0.93 2.43 3.206 (4) 140
O51—H51⋯O52iii 0.82 1.87 2.672 (3) 167
C24—H24⋯O62iii 0.93 2.54 3.461 (3) 170
O61—H61⋯O62v 0.82 1.83 2.648 (3) 178
C12—H12⋯O72i 0.93 2.59 3.255 (3) 129
C32—H32⋯O72 0.93 2.37 3.122 (4) 137
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x-1, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) x, y, z+1; (v) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART and SAINT for Windows NT. 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al., 2001). As part of an investigation of the coordination properties of Schiff bases functioning as ligands, we report the synthesis and structure of the title compound (I).

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The o-vanillin group (C21–C27/O22/O23) is essentially planar, with an r.m.s. deviation for fitted atoms of 0.0236 Å. This group makes dihedral angles of 9.50 (11)° and 42.86 (7)°, respectively, with the pyridine ring (C12—C16/N11) and the benzene ring (C31—C36). Furthermore, the dihedral angle between the pyridine ring (C12—C16/N11) and the benzene ring (C31—C36) is 50.43 (8)°.

The crystal packing is stabilized by N—H···O, O—H···O, O—H···N hydrogen bonds and C—H···O interactions (Table 1, Fig. 2), leading to an infinite network.

Related literature top

For general background, see: Allen et al. (1987); Jones et al. (1979); Larson & Pecoraro, (1991); Santos et al. (2001).

Experimental top

An anhydrous ethanol solution (50 ml) of 2-formyl-6-methoxyphenyl 4-chloro-3-nitrobenzenesulfonate (3.72 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of isonicotinohydrazide (1.37 g, 10 mmol) and the mixture stirred at 350 K for 5 h under nitrogen, giving a yellow precipitate. The product was isolated, recrystallized from ethanol and then dried in a vacuum to give the pure compound in 78% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetic acid solution.

Refinement top

The H atoms of the water molecule and imine group were located in difference maps and then treated as riding atoms. All other H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H, O—H and N—H bond lengths and isotropic U parameters: 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2—H; 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl C—H; 0.82 Å and Uiso(H) = 1.5Ueq(O) for hydroxyl O—H; 0.86 Å and Uiso(H) = 1.2Ueq(N) for imino N—H.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of compound (I), showing the formation of a complex network. For the sake of clarity, H atoms not involved in the hydrogen bonds shown have been omitted.
(E)-N'-[2-(4-Chloro-3-nitrophenylsulfonyloxy)-3- methoxybenzylidene]isonicotinohydrazide acetic acid tetrasolvate top
Crystal data top
C20H15ClN4O7S·4C2H4O2Z = 2
Mr = 731.09F(000) = 760
Triclinic, P1Dx = 1.451 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0565 (16) ÅCell parameters from 4854 reflections
b = 13.876 (3) Åθ = 2.2–28.0°
c = 16.097 (3) ŵ = 0.25 mm1
α = 79.01 (3)°T = 294 K
β = 76.01 (3)°Block, yellow
γ = 75.44 (3)°0.23 × 0.18 × 0.12 mm
V = 1673.8 (7) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5882 independent reflections
Radiation source: fine-focus sealed tube4448 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.913, Tmax = 0.970k = 1613
9794 measured reflectionsl = 1914
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0627P)2]
where P = (Fo2 + 2Fc2)/3
5882 reflections(Δ/σ)max = 0.001
451 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C20H15ClN4O7S·4C2H4O2γ = 75.44 (3)°
Mr = 731.09V = 1673.8 (7) Å3
Triclinic, P1Z = 2
a = 8.0565 (16) ÅMo Kα radiation
b = 13.876 (3) ŵ = 0.25 mm1
c = 16.097 (3) ÅT = 294 K
α = 79.01 (3)°0.23 × 0.18 × 0.12 mm
β = 76.01 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5882 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4448 reflections with I > 2σ(I)
Tmin = 0.913, Tmax = 0.970Rint = 0.081
9794 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å3
5882 reflectionsΔρmin = 0.44 e Å3
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 > 2σ(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
S10.36674 (7)0.89584 (4)0.99002 (5)0.01955 (19)
O10.2825 (2)0.90760 (14)1.07606 (14)0.0286 (5)
O20.5507 (2)0.85500 (13)0.96749 (14)0.0244 (5)
N111.0675 (2)0.32110 (15)1.23406 (16)0.0208 (5)
C121.1069 (3)0.27264 (19)1.1657 (2)0.0207 (6)
H121.18800.21171.16620.025*
C131.0324 (3)0.30910 (18)1.0941 (2)0.0201 (6)
H131.06300.27311.04750.024*
C140.9115 (3)0.40008 (17)1.09249 (18)0.0169 (6)
C150.8746 (3)0.45215 (19)1.1617 (2)0.0226 (6)
H150.79760.51461.16180.027*
C160.9547 (3)0.4098 (2)1.2318 (2)0.0247 (6)
H160.92840.44481.27880.030*
C170.8325 (3)0.43673 (18)1.01316 (19)0.0178 (6)
N170.7134 (2)0.52433 (14)1.01405 (16)0.0181 (5)
H170.68020.55431.05930.022*
O170.8782 (2)0.38954 (13)0.95161 (13)0.0238 (5)
C210.4519 (3)0.70078 (17)0.87464 (18)0.0164 (6)
C220.3222 (3)0.78844 (18)0.88440 (18)0.0155 (5)
O220.26276 (19)0.82421 (12)0.96469 (12)0.0177 (4)
C230.2359 (3)0.83875 (17)0.81745 (19)0.0189 (6)
O230.1050 (2)0.91963 (12)0.83710 (13)0.0214 (4)
C23A0.0280 (3)0.9805 (2)0.7665 (2)0.0268 (7)
H23A0.02910.94130.74400.040*
H23B0.11831.00290.72160.040*
H23C0.05611.03780.78710.040*
C240.2833 (3)0.80131 (18)0.73985 (19)0.0189 (6)
H240.22760.83350.69460.023*
C250.4150 (3)0.71516 (18)0.72938 (19)0.0200 (6)
H250.44750.69070.67650.024*
C260.4983 (3)0.66517 (18)0.7960 (2)0.0206 (6)
H260.58570.60750.78780.025*
C270.5316 (3)0.64754 (17)0.94872 (19)0.0178 (6)
H270.49930.67371.00080.021*
N270.6456 (2)0.56518 (14)0.94087 (15)0.0173 (5)
C310.3174 (3)1.00961 (18)0.92192 (19)0.0202 (6)
C320.4306 (3)1.02540 (18)0.8445 (2)0.0210 (6)
H320.53290.97810.82870.025*
C330.3873 (3)1.11389 (19)0.7910 (2)0.0230 (6)
N330.5045 (3)1.13006 (17)0.7079 (2)0.0342 (6)
O330.4431 (3)1.14733 (18)0.64263 (17)0.0503 (7)
O340.6588 (2)1.12465 (17)0.70740 (18)0.0486 (7)
C340.2382 (3)1.18656 (19)0.8158 (2)0.0246 (7)
Cl340.19242 (9)1.30033 (5)0.75118 (6)0.0351 (2)
C350.1276 (3)1.16966 (19)0.8944 (2)0.0244 (6)
H350.02731.21790.91110.029*
C360.1665 (3)1.08062 (19)0.9483 (2)0.0223 (6)
H360.09281.06821.00150.027*
C410.3533 (3)0.61046 (19)0.2126 (2)0.0254 (7)
O410.2137 (2)0.58404 (16)0.20296 (15)0.0329 (5)
H410.22250.57960.15190.049*
O420.4795 (2)0.61927 (15)0.15511 (15)0.0318 (5)
C420.3373 (4)0.6290 (3)0.3024 (2)0.0473 (9)
H42A0.44830.63600.30970.071*
H42B0.30200.57350.34240.071*
H42C0.25120.68960.31310.071*
C510.3163 (4)0.4268 (2)0.5144 (2)0.0378 (8)
O510.2940 (3)0.4842 (2)0.57278 (19)0.0548 (7)
H510.36720.51920.55830.082*
O520.4437 (3)0.42050 (18)0.45479 (18)0.0491 (6)
C520.1786 (5)0.3693 (3)0.5263 (3)0.0520 (10)
H52A0.16740.35860.47090.078*
H52B0.06910.40650.55490.078*
H52C0.20980.30560.56080.078*
C610.8864 (3)0.1393 (2)0.4933 (2)0.0299 (7)
O610.9839 (2)0.10855 (16)0.55199 (15)0.0348 (5)
H611.02880.04860.55140.052*
O620.8689 (3)0.08503 (15)0.44639 (16)0.0371 (6)
C620.7966 (4)0.2472 (2)0.4893 (2)0.0400 (8)
H62A0.67360.25270.51250.060*
H62B0.81370.27870.43020.060*
H62C0.84460.27990.52250.060*
C710.6959 (3)0.8590 (2)0.6418 (2)0.0239 (7)
O710.7975 (2)0.77024 (14)0.62854 (14)0.0272 (5)
H710.83380.74290.67250.041*
O720.6782 (2)0.89620 (14)0.70593 (15)0.0316 (5)
C720.6031 (3)0.9089 (2)0.5696 (2)0.0333 (8)
H72A0.48790.89500.58290.050*
H72B0.66790.88340.51710.050*
H72C0.59400.98010.56260.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0179 (3)0.0224 (4)0.0203 (4)0.0036 (2)0.0060 (3)0.0059 (3)
O10.0352 (10)0.0325 (11)0.0204 (13)0.0055 (8)0.0070 (9)0.0096 (9)
O20.0186 (8)0.0266 (10)0.0302 (13)0.0039 (7)0.0092 (8)0.0054 (9)
N110.0165 (10)0.0231 (12)0.0227 (15)0.0043 (8)0.0057 (10)0.0009 (11)
C120.0142 (11)0.0227 (14)0.0237 (18)0.0045 (9)0.0026 (11)0.0008 (12)
C130.0182 (11)0.0201 (13)0.0230 (17)0.0059 (9)0.0039 (11)0.0033 (12)
C140.0149 (11)0.0201 (13)0.0157 (16)0.0073 (9)0.0026 (11)0.0013 (11)
C150.0225 (12)0.0190 (13)0.0261 (18)0.0003 (10)0.0083 (12)0.0041 (12)
C160.0236 (12)0.0305 (15)0.0203 (18)0.0041 (11)0.0049 (12)0.0059 (13)
C170.0151 (11)0.0184 (13)0.0208 (17)0.0075 (10)0.0030 (11)0.0002 (12)
N170.0182 (9)0.0173 (11)0.0195 (14)0.0022 (8)0.0068 (10)0.0027 (10)
O170.0265 (9)0.0212 (10)0.0237 (13)0.0021 (7)0.0087 (9)0.0081 (9)
C210.0148 (10)0.0163 (13)0.0191 (16)0.0064 (9)0.0043 (11)0.0006 (11)
C220.0154 (11)0.0199 (13)0.0123 (15)0.0068 (9)0.0007 (10)0.0037 (11)
O220.0166 (8)0.0209 (9)0.0157 (11)0.0048 (6)0.0028 (8)0.0028 (8)
C230.0140 (11)0.0165 (13)0.0275 (18)0.0048 (9)0.0065 (11)0.0015 (12)
O230.0190 (8)0.0243 (9)0.0199 (12)0.0013 (7)0.0076 (8)0.0036 (8)
C23A0.0271 (13)0.0265 (14)0.0245 (19)0.0019 (11)0.0139 (13)0.0029 (13)
C240.0189 (11)0.0238 (14)0.0166 (16)0.0087 (10)0.0057 (11)0.0011 (12)
C250.0217 (12)0.0239 (14)0.0167 (16)0.0080 (10)0.0020 (11)0.0064 (12)
C260.0182 (11)0.0181 (13)0.0266 (18)0.0037 (10)0.0043 (12)0.0063 (12)
C270.0175 (11)0.0206 (13)0.0164 (16)0.0079 (10)0.0035 (11)0.0002 (11)
N270.0161 (9)0.0174 (11)0.0194 (14)0.0043 (8)0.0063 (9)0.0008 (9)
C310.0165 (11)0.0208 (13)0.0270 (18)0.0056 (9)0.0048 (12)0.0099 (12)
C320.0156 (11)0.0191 (13)0.0281 (18)0.0008 (9)0.0048 (12)0.0080 (12)
C330.0201 (12)0.0254 (14)0.0232 (18)0.0062 (10)0.0001 (12)0.0068 (12)
N330.0341 (13)0.0245 (13)0.0343 (19)0.0002 (10)0.0037 (12)0.0027 (12)
O330.0529 (13)0.0589 (15)0.0228 (15)0.0053 (11)0.0007 (12)0.0003 (12)
O340.0249 (10)0.0518 (14)0.0540 (19)0.0077 (9)0.0101 (11)0.0052 (12)
C340.0211 (12)0.0189 (13)0.036 (2)0.0016 (10)0.0101 (13)0.0067 (12)
Cl340.0359 (4)0.0236 (4)0.0399 (5)0.0018 (3)0.0083 (4)0.0007 (3)
C350.0187 (12)0.0229 (14)0.0305 (19)0.0001 (10)0.0027 (12)0.0102 (13)
C360.0162 (11)0.0262 (14)0.0263 (18)0.0056 (10)0.0008 (11)0.0112 (12)
C410.0258 (13)0.0254 (14)0.0229 (19)0.0002 (11)0.0073 (13)0.0027 (13)
O410.0276 (10)0.0474 (13)0.0254 (14)0.0059 (8)0.0047 (10)0.0127 (11)
O420.0275 (10)0.0381 (11)0.0261 (14)0.0023 (8)0.0008 (10)0.0080 (10)
C420.0498 (19)0.073 (2)0.027 (2)0.0286 (17)0.0041 (17)0.0110 (19)
C510.0457 (18)0.0357 (18)0.032 (2)0.0015 (14)0.0159 (17)0.0072 (16)
O510.0612 (15)0.0578 (16)0.050 (2)0.0169 (12)0.0004 (14)0.0288 (15)
O520.0518 (14)0.0538 (15)0.0441 (18)0.0069 (11)0.0038 (13)0.0264 (13)
C520.059 (2)0.061 (2)0.042 (3)0.0182 (17)0.0104 (19)0.0138 (19)
C610.0215 (13)0.0445 (18)0.0185 (18)0.0082 (12)0.0015 (12)0.0021 (15)
O610.0312 (10)0.0453 (12)0.0282 (14)0.0054 (9)0.0093 (10)0.0054 (10)
O620.0427 (12)0.0388 (12)0.0330 (15)0.0062 (9)0.0180 (11)0.0033 (11)
C620.0346 (15)0.0464 (19)0.034 (2)0.0027 (13)0.0053 (15)0.0036 (16)
C710.0169 (12)0.0291 (16)0.0236 (19)0.0072 (11)0.0007 (12)0.0002 (13)
O710.0268 (9)0.0301 (11)0.0226 (13)0.0001 (8)0.0089 (9)0.0017 (9)
O720.0359 (10)0.0298 (11)0.0283 (14)0.0003 (8)0.0091 (10)0.0086 (10)
C720.0278 (14)0.0384 (17)0.029 (2)0.0028 (12)0.0090 (14)0.0035 (14)
Geometric parameters (Å, º) top
S1—O11.408 (2)C32—C331.378 (4)
S1—O21.4303 (18)C32—H320.9300
S1—O221.6107 (17)C33—C341.390 (4)
S1—C311.757 (3)C33—N331.453 (4)
N11—C121.330 (4)N33—O331.225 (4)
N11—C161.334 (3)N33—O341.225 (3)
C12—C131.380 (4)C34—C351.377 (4)
C12—H120.9300C34—Cl341.726 (3)
C13—C141.388 (3)C35—C361.380 (4)
C13—H130.9300C35—H350.9300
C14—C151.375 (4)C36—H360.9300
C14—C171.509 (4)C41—O421.212 (3)
C15—C161.393 (4)C41—O411.318 (3)
C15—H150.9300C41—C421.486 (5)
C16—H160.9300O41—H410.8200
C17—O171.223 (3)C42—H42A0.9600
C17—N171.346 (3)C42—H42B0.9600
N17—N271.381 (3)C42—H42C0.9600
N17—H170.8600C51—O521.222 (4)
C21—C261.380 (4)C51—O511.297 (4)
C21—C221.397 (3)C51—C521.479 (5)
C21—C271.475 (3)O51—H510.8200
C22—C231.401 (3)C52—H52A0.9600
C22—O221.404 (3)C52—H52B0.9600
C23—O231.360 (3)C52—H52C0.9600
C23—C241.376 (4)C61—O621.216 (4)
O23—C23A1.450 (3)C61—O611.315 (3)
C23A—H23A0.9600C61—C621.487 (4)
C23A—H23B0.9600O61—H610.8200
C23A—H23C0.9600C62—H62A0.9600
C24—C251.391 (4)C62—H62B0.9600
C24—H240.9300C62—H62C0.9600
C25—C261.383 (4)C71—O721.203 (4)
C25—H250.9300C71—O711.320 (3)
C26—H260.9300C71—C721.497 (4)
C27—N271.279 (3)O71—H710.8200
C27—H270.9300C72—H72A0.9600
C31—C321.371 (4)C72—H72B0.9600
C31—C361.392 (4)C72—H72C0.9600
O1—S1—O2121.40 (12)C36—C31—S1119.3 (2)
O1—S1—O22103.04 (11)C31—C32—C33117.6 (2)
O2—S1—O22108.77 (10)C31—C32—H32121.2
O1—S1—C31110.02 (13)C33—C32—H32121.2
O2—S1—C31108.32 (12)C32—C33—C34121.4 (3)
O22—S1—C31103.83 (10)C32—C33—N33117.9 (2)
C12—N11—C16118.2 (2)C34—C33—N33120.7 (2)
N11—C12—C13122.7 (2)O33—N33—O34124.1 (3)
N11—C12—H12118.6O33—N33—C33118.0 (2)
C13—C12—H12118.6O34—N33—C33117.9 (3)
C12—C13—C14119.2 (3)C35—C34—C33120.0 (2)
C12—C13—H13120.4C35—C34—Cl34119.0 (2)
C14—C13—H13120.4C33—C34—Cl34121.0 (2)
C15—C14—C13118.3 (2)C34—C35—C36119.6 (2)
C15—C14—C17124.2 (2)C34—C35—H35120.2
C13—C14—C17117.4 (3)C36—C35—H35120.2
C14—C15—C16118.9 (2)C35—C36—C31119.1 (3)
C14—C15—H15120.6C35—C36—H36120.4
C16—C15—H15120.6C31—C36—H36120.4
N11—C16—C15122.6 (3)O42—C41—O41124.2 (3)
N11—C16—H16118.7O42—C41—C42123.9 (2)
C15—C16—H16118.7O41—C41—C42111.9 (3)
O17—C17—N17122.8 (2)C41—O41—H41109.5
O17—C17—C14121.1 (2)C41—C42—H42A109.5
N17—C17—C14116.1 (3)C41—C42—H42B109.5
C17—N17—N27118.7 (2)H42A—C42—H42B109.5
C17—N17—H17120.7C41—C42—H42C109.5
N27—N17—H17120.7H42A—C42—H42C109.5
C26—C21—C22118.6 (2)H42B—C42—H42C109.5
C26—C21—C27121.9 (2)O52—C51—O51121.7 (3)
C22—C21—C27119.5 (3)O52—C51—C52123.1 (3)
C21—C22—C23121.7 (3)O51—C51—C52115.2 (3)
C21—C22—O22120.7 (2)C51—O51—H51109.5
C23—C22—O22117.4 (2)C51—C52—H52A109.5
C22—O22—S1119.17 (15)C51—C52—H52B109.5
O23—C23—C24125.5 (2)H52A—C52—H52B109.5
O23—C23—C22115.7 (3)C51—C52—H52C109.5
C24—C23—C22118.7 (2)H52A—C52—H52C109.5
C23—O23—C23A116.9 (2)H52B—C52—H52C109.5
O23—C23A—H23A109.5O62—C61—O61123.7 (3)
O23—C23A—H23B109.5O62—C61—C62122.3 (3)
H23A—C23A—H23B109.5O61—C61—C62114.1 (3)
O23—C23A—H23C109.5C61—O61—H61109.5
H23A—C23A—H23C109.5C61—C62—H62A109.5
H23B—C23A—H23C109.5C61—C62—H62B109.5
C23—C24—C25119.7 (2)H62A—C62—H62B109.5
C23—C24—H24120.1C61—C62—H62C109.5
C25—C24—H24120.1H62A—C62—H62C109.5
C26—C25—C24121.3 (3)H62B—C62—H62C109.5
C26—C25—H25119.3O72—C71—O71123.4 (2)
C24—C25—H25119.3O72—C71—C72123.0 (3)
C21—C26—C25120.0 (2)O71—C71—C72113.5 (3)
C21—C26—H26120.0C71—O71—H71109.5
C25—C26—H26120.0C71—C72—H72A109.5
N27—C27—C21119.6 (3)C71—C72—H72B109.5
N27—C27—H27120.2H72A—C72—H72B109.5
C21—C27—H27120.2C71—C72—H72C109.5
C27—N27—N17113.8 (2)H72A—C72—H72C109.5
C32—C31—C36122.3 (2)H72B—C72—H72C109.5
C32—C31—S1118.43 (19)
C16—N11—C12—C131.8 (3)C23—C24—C25—C260.8 (3)
N11—C12—C13—C140.1 (4)C22—C21—C26—C251.0 (3)
C12—C13—C14—C152.1 (3)C27—C21—C26—C25177.3 (2)
C12—C13—C14—C17179.6 (2)C24—C25—C26—C210.3 (3)
C13—C14—C15—C162.5 (3)C26—C21—C27—N271.0 (3)
C17—C14—C15—C16179.3 (2)C22—C21—C27—N27177.3 (2)
C12—N11—C16—C151.4 (4)C21—C27—N27—N17178.38 (18)
C14—C15—C16—N110.8 (4)C17—N17—N27—C27179.00 (19)
C15—C14—C17—O17175.8 (2)O1—S1—C31—C32156.83 (19)
C13—C14—C17—O172.4 (3)O2—S1—C31—C3222.0 (2)
C15—C14—C17—N172.9 (3)O22—S1—C31—C3293.5 (2)
C13—C14—C17—N17178.9 (2)O1—S1—C31—C3622.8 (2)
O17—C17—N17—N273.1 (3)O2—S1—C31—C36157.57 (19)
C14—C17—N17—N27175.57 (18)O22—S1—C31—C3686.9 (2)
C26—C21—C22—C231.8 (3)C36—C31—C32—C332.1 (4)
C27—C21—C22—C23176.5 (2)S1—C31—C32—C33178.31 (18)
C26—C21—C22—O22176.0 (2)C31—C32—C33—C342.6 (4)
C27—C21—C22—O222.3 (3)C31—C32—C33—N33178.5 (2)
C21—C22—O22—S186.2 (2)C32—C33—N33—O33123.9 (3)
C23—C22—O22—S199.4 (2)C34—C33—N33—O3357.3 (4)
O1—S1—O22—C22174.26 (16)C32—C33—N33—O3455.5 (3)
O2—S1—O22—C2244.21 (18)C34—C33—N33—O34123.4 (3)
C31—S1—O22—C2270.97 (19)C32—C33—C34—C351.9 (4)
C21—C22—C23—O23176.15 (19)N33—C33—C34—C35179.3 (2)
O22—C22—C23—O231.7 (3)C32—C33—C34—Cl34175.97 (19)
C21—C22—C23—C241.2 (3)N33—C33—C34—Cl342.9 (4)
O22—C22—C23—C24175.7 (2)C33—C34—C35—C360.5 (4)
C24—C23—O23—C23A10.3 (3)Cl34—C34—C35—C36177.41 (19)
C22—C23—O23—C23A172.6 (2)C34—C35—C36—C310.1 (4)
O23—C23—C24—C25177.2 (2)C32—C31—C36—C350.8 (4)
C22—C23—C24—C250.1 (3)S1—C31—C36—C35179.63 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O71—H71···N11i0.821.842.661 (3)176
C35—H35···O17ii0.932.513.360 (3)152
O41—H41···O17iii0.821.962.698 (3)150
O41—H41···N27iii0.822.593.211 (3)134
N17—H17···O42iv0.862.102.875 (3)150
C27—H27···O42iv0.932.433.206 (4)140
O51—H51···O52iii0.821.872.672 (3)167
C24—H24···O62iii0.932.543.461 (3)170
O61—H61···O62v0.821.832.648 (3)178
C12—H12···O72i0.932.593.255 (3)129
C32—H32···O720.932.373.122 (4)137
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, y+1, z; (iii) x+1, y+1, z+1; (iv) x, y, z+1; (v) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC20H15ClN4O7S·4C2H4O2
Mr731.09
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)8.0565 (16), 13.876 (3), 16.097 (3)
α, β, γ (°)79.01 (3), 76.01 (3), 75.44 (3)
V3)1673.8 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.23 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.913, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
9794, 5882, 4448
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.146, 1.01
No. of reflections5882
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.44

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O71—H71···N11i0.821.842.661 (3)176
C35—H35···O17ii0.932.513.360 (3)152
O41—H41···O17iii0.821.962.698 (3)150
O41—H41···N27iii0.822.593.211 (3)134
N17—H17···O42iv0.862.102.875 (3)150
C27—H27···O42iv0.932.433.206 (4)140
O51—H51···O52iii0.821.872.672 (3)167
C24—H24···O62iii0.932.543.461 (3)170
O61—H61···O62v0.821.832.648 (3)178
C12—H12···O72i0.932.593.255 (3)129
C32—H32···O720.932.373.122 (4)137
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, y+1, z; (iii) x+1, y+1, z+1; (iv) x, y, z+1; (v) x+2, y, z+1.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (1999). SMART and SAINT for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationJones, R. D., Summerville, D. A. & Basolo, F. (1979). Chem. Rev. 17, 139–179.  CrossRef Web of Science Google Scholar
First citationLarson, E. J. & Pecoraro, V. L. (1991). J. Am. Chem. Soc. 113, 3810–3818.  CSD CrossRef CAS Web of Science Google Scholar
First citationSantos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844.  Web of Science CrossRef 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 citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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