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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,5-Bis[1-(2,4-dihy­dr­oxy­phen­yl)ethyl­­idene]carbonohydrazide di­methyl­formamide disolvate

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and bLiaocheng International Peace Hospital, Shandong 252059, People's Republic of China
*Correspondence e-mail: heqp2008@163.com

(Received 15 October 2010; accepted 22 October 2010; online 30 October 2010)

In the title compound, C17H18N4O5·2C3H7NO, two solvent mol­ecules are linked to the main mol­ecule via N—H⋯O and O—H⋯O hydrogen bonds, forming a hydrogen-bonded trimer. Intra­molecular O—H⋯N hydrogen bonds influence the mol­ecular conformation of the main mol­ecule, and the two benzene rings form a dihedral angle of 10.55 (18)°. In the crystal, inter­molecular O—H⋯O hydrogen bonds link hydrogen-bonded trimers into ribbons extending along the b axis.

Related literature

For the biological activity of carbonohydrazide derivatives, see: Loncle et al. (2004[Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067-1071.]); Li et al. (2004[Li, M. X., Cai, P., Duan, C. Y., Lu, F., Xie, J. & Meng, Q. J. (2004). Inorg. Chem. 43, 5174-5176.]). For a related structure, see: Zukerman-Schpector et al. (2009[Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N4O5·2C3H7NO

  • Mr = 504.55

  • Monoclinic, P 21 /n

  • a = 11.3506 (11) Å

  • b = 9.0160 (7) Å

  • c = 24.953 (3) Å

  • β = 97.546 (1)°

  • V = 2531.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 K

  • 0.50 × 0.37 × 0.35 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 = 0.952, Tmax = 0.966

  • 12361 measured reflections

  • 4466 independent reflections

  • 2158 reflections with I > 2σ(I)

  • Rint = 0.055

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.152

  • S = 1.03

  • 4466 reflections

  • 331 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.82 1.83 2.549 (3) 145
O3—H3⋯N4 0.82 1.84 2.562 (3) 146
O2—H2⋯O7 0.82 1.90 2.704 (4) 168
N2—H2′⋯O6 0.86 2.13 2.918 (3) 153
N3—H3′⋯O6 0.86 2.16 2.932 (3) 149
O4—H4⋯O5i 0.82 1.86 2.680 (3) 173
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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

Carbonohydrazide Schiff base derivatives are known to exhibit a wide range of interesting biological activities, including antibacterial antifungal, anticonvulsant, anticancer activities as well as herbicidal and fungicidal activity (Loncle et al., 2004; Li et al., 2004). Herewith we present the crystal structure of the title compound (I) - a new carbonohydrazide derivative.

In (I) (Fig. 1), the bond lengths and angles of the main molecule are normal and correspond to those observed in N'',N'''-bis (1-(2-hydroxyphenyl)ethylidene)carbonohydrazide dimethyl sulfoxide solvate (Zukerman-Schpector et al., 2009). The intramolecular O—H···N hydrogen bonds (Table 1) influence the molecular conformation. Two DMF solvent molecules are linked to the main molecule via N—H···O and O—H···O hydrogen bonds (Table 1) forming a hydrogen-bonded trimer (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) link hydrogen-bonded trimers into ribbons extended along the b axis.

Related literature top

For the biological activity of carbonohydrazide derivatives, see: Loncle et al. (2004); Li et al. (2004). For a related structure, see: Zukerman-Schpector et al. (2009).

Experimental top

2, 4-Dihydroxylacetophenone (10.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash. After 3h stirring at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from DMF, and afforded the title compound as a crystalline solid.

Refinement top

All H atoms were placed in idealized positions (C—H 0.93–0.96 Å, N—H 0.86 Å, O—H 0.82 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(parent atom).

Structure description top

Carbonohydrazide Schiff base derivatives are known to exhibit a wide range of interesting biological activities, including antibacterial antifungal, anticonvulsant, anticancer activities as well as herbicidal and fungicidal activity (Loncle et al., 2004; Li et al., 2004). Herewith we present the crystal structure of the title compound (I) - a new carbonohydrazide derivative.

In (I) (Fig. 1), the bond lengths and angles of the main molecule are normal and correspond to those observed in N'',N'''-bis (1-(2-hydroxyphenyl)ethylidene)carbonohydrazide dimethyl sulfoxide solvate (Zukerman-Schpector et al., 2009). The intramolecular O—H···N hydrogen bonds (Table 1) influence the molecular conformation. Two DMF solvent molecules are linked to the main molecule via N—H···O and O—H···O hydrogen bonds (Table 1) forming a hydrogen-bonded trimer (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) link hydrogen-bonded trimers into ribbons extended along the b axis.

For the biological activity of carbonohydrazide derivatives, see: Loncle et al. (2004); Li et al. (2004). For a related structure, see: Zukerman-Schpector et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids. Dashed lines denote intermolecular hydrogen bonds.
1,5-Bis[1-(2,4-dihydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide disolvate top
Crystal data top
C17H18N4O5·2C3H7NOF(000) = 1072
Mr = 504.55Dx = 1.324 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.3506 (11) ÅCell parameters from 2127 reflections
b = 9.0160 (7) Åθ = 2.9–23.9°
c = 24.953 (3) ŵ = 0.10 mm1
β = 97.546 (1)°T = 298 K
V = 2531.5 (4) Å3Block, colourless
Z = 40.50 × 0.37 × 0.35 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4466 independent reflections
Radiation source: fine-focus sealed tube2158 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1113
Tmin = 0.952, Tmax = 0.966k = 1010
12361 measured reflectionsl = 2927
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.4683P]
where P = (Fo2 + 2Fc2)/3
4466 reflections(Δ/σ)max = 0.009
331 parametersΔρmax = 0.30 e Å3
1 restraintΔρmin = 0.27 e Å3
Crystal data top
C17H18N4O5·2C3H7NOV = 2531.5 (4) Å3
Mr = 504.55Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.3506 (11) ŵ = 0.10 mm1
b = 9.0160 (7) ÅT = 298 K
c = 24.953 (3) Å0.50 × 0.37 × 0.35 mm
β = 97.546 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4466 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2158 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.966Rint = 0.055
12361 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0511 restraint
wR(F2) = 0.152H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å3
4466 reflectionsΔρmin = 0.27 e Å3
331 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
N30.5482 (2)1.0132 (3)0.38574 (9)0.0413 (7)
H3'0.62331.02030.39610.050*
N40.4960 (2)1.0910 (3)0.34129 (9)0.0379 (7)
N10.4829 (2)0.7684 (3)0.48746 (9)0.0362 (7)
N20.5404 (2)0.8673 (3)0.45843 (9)0.0375 (7)
H2'0.61310.89210.46870.045*
C10.4790 (3)0.9250 (4)0.41282 (12)0.0352 (8)
C20.5629 (3)1.1733 (4)0.31528 (12)0.0371 (8)
O10.29729 (18)0.6107 (3)0.49012 (9)0.0542 (7)
H10.34140.66800.47670.081*
O40.34283 (19)1.5034 (3)0.13770 (9)0.0537 (7)
H40.27431.47580.12860.081*
C40.5033 (3)1.2567 (4)0.26924 (11)0.0346 (8)
C120.4686 (3)0.6037 (3)0.55900 (11)0.0348 (8)
O50.37418 (19)0.8984 (3)0.39800 (9)0.0519 (7)
C100.5368 (3)0.7104 (3)0.53123 (12)0.0353 (8)
C70.3926 (3)1.4211 (4)0.18086 (12)0.0405 (8)
C60.3283 (3)1.3208 (4)0.20663 (12)0.0406 (8)
H140.24801.30680.19460.049*
O30.31113 (19)1.1458 (3)0.27370 (9)0.0607 (7)
H30.35051.10270.29890.091*
C140.2910 (3)0.4568 (4)0.56516 (13)0.0465 (9)
H160.21400.43070.55090.056*
C130.3532 (3)0.5593 (4)0.53799 (12)0.0391 (8)
C90.5651 (3)1.3599 (4)0.24144 (13)0.0476 (9)
H180.64571.37380.25260.057*
C50.3820 (3)1.2408 (4)0.25034 (12)0.0378 (8)
C170.5158 (3)0.5373 (4)0.60781 (13)0.0472 (9)
H200.59230.56340.62280.057*
C150.3419 (3)0.3934 (4)0.61297 (14)0.0460 (9)
C160.4555 (3)0.4360 (4)0.63457 (13)0.0500 (9)
H220.49060.39580.66710.060*
O20.2771 (2)0.2926 (3)0.63652 (10)0.0647 (7)
H20.31370.26670.66550.097*
C80.5119 (3)1.4409 (4)0.19856 (13)0.0482 (9)
H240.55601.50900.18150.058*
C110.6630 (3)0.7461 (4)0.55445 (13)0.0512 (9)
H26A0.67540.85120.55300.077*
H26B0.71680.69640.53380.077*
H26C0.67710.71330.59130.077*
C30.6951 (3)1.1842 (4)0.33107 (14)0.0601 (11)
H32A0.71171.24730.36210.090*
H32B0.73101.22500.30160.090*
H32C0.72711.08720.33960.090*
O60.7696 (2)1.0156 (3)0.46093 (10)0.0652 (8)
C180.8226 (3)1.0859 (4)0.49864 (15)0.0531 (10)
H18A0.79161.08230.53130.064*
N50.9189 (2)1.1658 (3)0.49747 (12)0.0555 (8)
C200.9664 (4)1.1869 (5)0.44770 (17)0.0911 (15)
H20A0.92351.12620.42010.137*
H20B1.04881.15940.45230.137*
H20C0.95871.28930.43720.137*
C190.9714 (4)1.2474 (5)0.54508 (17)0.0898 (15)
H19A0.93111.22170.57530.135*
H19B0.96361.35190.53830.135*
H19C1.05401.22220.55300.135*
N60.5058 (3)0.0928 (4)0.80215 (12)0.0562 (8)
C230.4210 (3)0.0012 (4)0.82410 (14)0.0664 (11)
H23A0.34540.00590.80190.100*
H23B0.41300.03020.86020.100*
H23C0.44820.10200.82470.100*
C220.4740 (4)0.1708 (5)0.75761 (18)0.0661 (11)
H22A0.53260.22780.74480.079*
C210.6253 (3)0.0985 (5)0.83068 (17)0.0882 (14)
H21A0.67260.16500.81230.132*
H21B0.65980.00110.83180.132*
H21C0.62280.13320.86690.132*
O70.3748 (2)0.1750 (3)0.73179 (11)0.0717 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N30.0364 (15)0.0483 (19)0.0378 (15)0.0007 (14)0.0007 (12)0.0098 (14)
N40.0402 (15)0.0406 (18)0.0319 (15)0.0063 (14)0.0004 (12)0.0065 (13)
N10.0425 (16)0.0320 (17)0.0338 (15)0.0011 (13)0.0043 (13)0.0017 (13)
N20.0347 (14)0.0403 (18)0.0360 (15)0.0025 (13)0.0015 (12)0.0051 (13)
C10.040 (2)0.032 (2)0.0328 (18)0.0046 (16)0.0008 (16)0.0022 (16)
C20.0377 (18)0.042 (2)0.0318 (18)0.0001 (17)0.0061 (15)0.0038 (16)
O10.0406 (13)0.0608 (19)0.0587 (16)0.0030 (12)0.0026 (12)0.0149 (13)
O40.0482 (14)0.0626 (18)0.0477 (14)0.0000 (13)0.0038 (11)0.0189 (13)
C40.0378 (18)0.037 (2)0.0282 (17)0.0016 (16)0.0029 (14)0.0016 (15)
C120.0416 (19)0.030 (2)0.0327 (18)0.0023 (16)0.0054 (15)0.0018 (15)
O50.0396 (13)0.0582 (17)0.0542 (14)0.0065 (12)0.0077 (11)0.0107 (12)
C100.0405 (18)0.030 (2)0.0348 (18)0.0011 (16)0.0024 (15)0.0051 (16)
C70.0394 (19)0.047 (2)0.0347 (18)0.0055 (17)0.0017 (15)0.0038 (17)
C60.0298 (17)0.048 (2)0.0434 (19)0.0005 (17)0.0016 (15)0.0085 (18)
O30.0432 (14)0.072 (2)0.0669 (18)0.0047 (14)0.0067 (12)0.0319 (14)
C140.042 (2)0.042 (2)0.057 (2)0.0006 (17)0.0128 (17)0.0010 (19)
C130.0417 (19)0.036 (2)0.0395 (19)0.0052 (17)0.0044 (16)0.0005 (16)
C90.0382 (19)0.059 (3)0.044 (2)0.0081 (18)0.0004 (16)0.0053 (19)
C50.0373 (19)0.041 (2)0.0373 (18)0.0001 (17)0.0119 (15)0.0050 (16)
C170.051 (2)0.045 (2)0.045 (2)0.0019 (18)0.0012 (17)0.0013 (18)
C150.056 (2)0.038 (2)0.049 (2)0.0041 (19)0.0249 (19)0.0009 (18)
C160.065 (2)0.047 (2)0.039 (2)0.000 (2)0.0053 (18)0.0057 (18)
O20.0669 (17)0.0618 (19)0.0703 (19)0.0031 (15)0.0271 (13)0.0148 (15)
C80.042 (2)0.054 (3)0.047 (2)0.0096 (18)0.0022 (16)0.0161 (19)
C110.049 (2)0.051 (2)0.050 (2)0.0088 (18)0.0045 (16)0.0054 (18)
C30.043 (2)0.080 (3)0.055 (2)0.005 (2)0.0022 (17)0.019 (2)
O60.0573 (16)0.076 (2)0.0581 (16)0.0114 (15)0.0095 (13)0.0035 (15)
C180.047 (2)0.061 (3)0.051 (2)0.001 (2)0.0053 (18)0.008 (2)
N50.0405 (17)0.061 (2)0.065 (2)0.0069 (16)0.0060 (15)0.0056 (18)
C200.069 (3)0.113 (4)0.096 (3)0.006 (3)0.025 (3)0.036 (3)
C190.079 (3)0.084 (4)0.099 (3)0.032 (3)0.016 (3)0.016 (3)
N60.054 (2)0.055 (2)0.060 (2)0.0052 (17)0.0098 (16)0.0024 (18)
C230.079 (3)0.063 (3)0.061 (2)0.005 (2)0.025 (2)0.005 (2)
C220.073 (3)0.055 (3)0.076 (3)0.007 (2)0.033 (2)0.000 (2)
C210.072 (3)0.099 (4)0.089 (3)0.017 (3)0.004 (2)0.012 (3)
O70.0652 (18)0.078 (2)0.0736 (19)0.0075 (16)0.0137 (15)0.0123 (16)
Geometric parameters (Å, º) top
N3—C11.358 (4)C15—O21.352 (4)
N3—N41.379 (3)C15—C161.385 (4)
N3—H3'0.8600C16—H220.9300
N4—C21.295 (4)O2—H20.8200
N1—C101.291 (3)C8—H240.9300
N1—N21.368 (3)C11—H26A0.9600
N2—C11.358 (3)C11—H26B0.9600
N2—H2'0.8600C11—H26C0.9600
C1—O51.223 (3)C3—H32A0.9600
C2—C41.462 (4)C3—H32B0.9600
C2—C31.504 (4)C3—H32C0.9600
O1—C131.359 (3)O6—C181.225 (4)
O1—H10.8200C18—N51.312 (4)
O4—C71.367 (3)C18—H18A0.9300
O4—H40.8200N5—C201.430 (4)
C4—C91.402 (4)N5—C191.456 (4)
C4—C51.403 (4)C20—H20A0.9600
C12—C171.400 (4)C20—H20B0.9600
C12—C131.403 (4)C20—H20C0.9600
C12—C101.465 (4)C19—H19A0.9600
C10—C111.507 (4)C19—H19B0.9600
C7—C61.374 (4)C19—H19C0.9600
C7—C81.380 (4)N6—C221.325 (5)
C6—C51.381 (4)N6—C231.443 (4)
C6—H140.9300N6—C211.447 (4)
O3—C51.358 (3)C23—H23A0.9600
O3—H30.8200C23—H23B0.9600
C14—C151.380 (4)C23—H23C0.9600
C14—C131.392 (4)C22—O71.222 (4)
C14—H160.9300C22—H22A0.9300
C9—C81.369 (4)C21—H21A0.9600
C9—H180.9300C21—H21B0.9600
C17—C161.367 (4)C21—H21C0.9600
C17—H200.9300
C1—N3—N4118.9 (2)C15—O2—H2109.5
C1—N3—H3'120.6C9—C8—C7119.6 (3)
N4—N3—H3'120.6C9—C8—H24120.2
C2—N4—N3118.5 (3)C7—C8—H24120.2
C10—N1—N2120.4 (2)C10—C11—H26A109.5
C1—N2—N1117.7 (3)C10—C11—H26B109.5
C1—N2—H2'121.1H26A—C11—H26B109.5
N1—N2—H2'121.1C10—C11—H26C109.5
O5—C1—N3124.6 (3)H26A—C11—H26C109.5
O5—C1—N2123.4 (3)H26B—C11—H26C109.5
N3—C1—N2112.0 (3)C2—C3—H32A109.5
N4—C2—C4116.5 (3)C2—C3—H32B109.5
N4—C2—C3122.5 (3)H32A—C3—H32B109.5
C4—C2—C3121.0 (3)C2—C3—H32C109.5
C13—O1—H1109.5H32A—C3—H32C109.5
C7—O4—H4109.5H32B—C3—H32C109.5
C9—C4—C5115.7 (3)O6—C18—N5126.4 (4)
C9—C4—C2121.3 (3)O6—C18—H18A116.8
C5—C4—C2123.0 (3)N5—C18—H18A116.8
C17—C12—C13115.8 (3)C18—N5—C20120.1 (3)
C17—C12—C10121.8 (3)C18—N5—C19120.8 (3)
C13—C12—C10122.4 (3)C20—N5—C19118.7 (3)
N1—C10—C12116.4 (3)N5—C20—H20A109.5
N1—C10—C11124.1 (3)N5—C20—H20B109.5
C12—C10—C11119.6 (3)H20A—C20—H20B109.5
C6—C7—O4122.4 (3)N5—C20—H20C109.5
C6—C7—C8119.7 (3)H20A—C20—H20C109.5
O4—C7—C8117.9 (3)H20B—C20—H20C109.5
C7—C6—C5120.4 (3)N5—C19—H19A109.5
C7—C6—H14119.8N5—C19—H19B109.5
C5—C6—H14119.8H19A—C19—H19B109.5
C5—O3—H3109.5N5—C19—H19C109.5
C15—C14—C13121.0 (3)H19A—C19—H19C109.5
C15—C14—H16119.5H19B—C19—H19C109.5
C13—C14—H16119.5C22—N6—C23120.5 (3)
O1—C13—C14116.5 (3)C22—N6—C21121.9 (4)
O1—C13—C12122.4 (3)C23—N6—C21117.6 (3)
C14—C13—C12121.1 (3)N6—C23—H23A109.5
C8—C9—C4122.9 (3)N6—C23—H23B109.5
C8—C9—H18118.5H23A—C23—H23B109.5
C4—C9—H18118.5N6—C23—H23C109.5
O3—C5—C6116.3 (3)H23A—C23—H23C109.5
O3—C5—C4122.1 (3)H23B—C23—H23C109.5
C6—C5—C4121.6 (3)O7—C22—N6126.1 (4)
C16—C17—C12123.5 (3)O7—C22—H22A116.9
C16—C17—H20118.2N6—C22—H22A116.9
C12—C17—H20118.2N6—C21—H21A109.5
O2—C15—C14117.7 (3)N6—C21—H21B109.5
O2—C15—C16123.3 (3)H21A—C21—H21B109.5
C14—C15—C16119.0 (3)N6—C21—H21C109.5
C17—C16—C15119.7 (3)H21A—C21—H21C109.5
C17—C16—H22120.2H21B—C21—H21C109.5
C15—C16—H22120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.549 (3)145
O3—H3···N40.821.842.562 (3)146
O2—H2···O70.821.902.704 (4)168
N2—H2···O60.862.132.918 (3)153
N3—H3···O60.862.162.932 (3)149
O4—H4···O5i0.821.862.680 (3)173
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H18N4O5·2C3H7NO
Mr504.55
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)11.3506 (11), 9.0160 (7), 24.953 (3)
β (°) 97.546 (1)
V3)2531.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.37 × 0.35
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.952, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
12361, 4466, 2158
Rint0.055
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.152, 1.03
No. of reflections4466
No. of parameters331
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.549 (3)145.2
O3—H3···N40.821.842.562 (3)145.5
O2—H2···O70.821.902.704 (4)168
N2—H2'···O60.862.132.918 (3)153
N3—H3'···O60.862.162.932 (3)149
O4—H4···O5i0.821.862.680 (3)173.2
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

This project was supported by the University Student Science and Technology Culture Foundation of Liaocheng University (grant No. SRT10056HX2) and the Foundation of Liaocheng University (grant No. X09010).

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, M. X., Cai, P., Duan, C. Y., Lu, F., Xie, J. & Meng, Q. J. (2004). Inorg. Chem. 43, 5174–5176.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationLoncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067–1071.  Web of Science 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 citationZukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951.  Web of Science CrossRef IUCr Journals Google Scholar

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