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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o372.
Published online 2009 January 23. doi:  10.1107/S1600536809002232
PMCID: PMC2968174

N,N′-Diacetyl-N′-[(4-nitro­phen­oxy)acetyl]acetohydrazide

Abstract

The asymmetric unit of the title compound, C14H15N3O7, contains two independent mol­ecules which are linked into a pseudocentrosymmetric dimer by a π–π inter­action, as shown by the short distance of 3.722 (5) Å between the centroids of the benzene rings. An extensive network of weak inter­molecular C—H(...)O hydrogen bonds helps to stabilize the crystal packing.

Related literature

For useful applications of hydrazide derivatives, see: Pang et al. (2005 [triangle]); Lutun et al. (1999 [triangle]); Liras et al. (2000 [triangle]); Dhadialla et al. (1998 [triangle]).

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Object name is e-65-0o372-scheme1.jpg

Experimental

Crystal data

  • C14H15N3O7
  • M r = 337.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o372-efi1.jpg
  • a = 14.949 (3) Å
  • b = 11.723 (2) Å
  • c = 23.034 (7) Å
  • β = 127.73 (2)°
  • V = 3192.6 (15) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 113 (2) K
  • 0.28 × 0.24 × 0.18 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.969, T max = 0.980
  • 21295 measured reflections
  • 5619 independent reflections
  • 2699 reflections with I > 2σ(I)
  • R int = 0.082

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.152
  • S = 0.90
  • 5619 reflections
  • 439 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected interatomic distances (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002232/cv2509sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002232/cv2509Isup2.hkl

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

supplementary crystallographic information

Comment

Hydrazide derivates were extensively used in material, chemical and medical industy. N-(4-Alkoxybenzoyl)-N'-(4'-aminobenzoyl) hydrazine was used as a liquid crystalline material (Pang et al., 2005) and bisacylhydrazines were a kind of insecticides (Dhadialla et al., 1998). Hydrazide derivates were also important intermediates in the synthesis of 1,3,4-oxadiazole (Lutun et al., 1999; Liras et al., 2000), which was a significant heterocycle in chemical industy. In order to investigate its activity in anti-hyperglycaemia, we have synthesized the title compound.

The asymmetric unit of the title compound, C14H15N3O7, contains two independent molecules, which are linked into pseudo-centrosymmetric dimer by π–π interaction proved by short distance of 3.722 (5) Å between the centroids of benzene rings C1–C6 and C15–C20 (Table 1). An extensive network of weak intermolecular C—H···O hydrogen bonds (Table 2) help to stabilize the crystal packing.

Experimental

1-Nitro-4-phenoxyacethydrazide (2.11 g, 0.01 mol) was dissolved in 30 ml of acetic anhydride. The solution was heated to reflux and stirred for 3 h and then cooled to room temperature. 300 ml of water were added and the precipitate formed was filtrated. The filter was wash with water and dried to give the title compound as a yellow powder (2.50 g, yield 76.4%, mp 400–402 K). The crystals suitable for the X-ray diffraction were obtained via slow evaporation of a solution of the title compound in dichloromethane/ethyl acetate/petroleum ether (1:1:1 v/v) at room temperature.

Refinement

All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 (1.5 for methyl) times Ueq(C).

Figures

Fig. 1.
Two independent molecules of the title compound, with displacement ellipsoids drawn at the 40% probability level.

Crystal data

C14H15N3O7F(000) = 1408
Mr = 337.29Dx = 1.403 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5002 reflections
a = 14.949 (3) Åθ = 1.7–27.7°
b = 11.723 (2) ŵ = 0.11 mm1
c = 23.034 (7) ÅT = 113 K
β = 127.73 (2)°Block, yellow
V = 3192.6 (15) Å30.28 × 0.24 × 0.18 mm
Z = 8

Data collection

Rigaku Saturn diffractometer5619 independent reflections
Radiation source: rotating anode2699 reflections with I > 2σ(I)
confocalRint = 0.082
ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)h = −16→17
Tmin = 0.969, Tmax = 0.980k = −13→13
21295 measured reflectionsl = −25→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3
5619 reflections(Δ/σ)max = 0.001
439 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.24 e Å3

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
O80.2333 (2)0.8689 (2)0.21267 (15)0.0989 (9)
O90.1368 (3)0.8437 (2)0.25247 (17)0.1111 (11)
O100.42854 (18)0.40509 (18)0.37921 (12)0.0621 (6)
O110.6321 (2)0.49597 (19)0.46900 (13)0.0748 (7)
O120.6482 (2)0.2300 (2)0.36527 (15)0.0855 (8)
O130.8291 (2)0.3120 (2)0.57451 (13)0.0753 (7)
O140.9409 (3)0.5835 (2)0.52505 (16)0.0881 (8)
N40.2110 (3)0.8155 (2)0.24781 (17)0.0722 (8)
N50.7227 (2)0.38153 (19)0.44137 (13)0.0484 (6)
N60.8218 (2)0.43821 (19)0.49755 (14)0.0488 (6)
C150.4096 (3)0.5723 (3)0.30951 (17)0.0579 (9)
H15A0.46430.54660.30540.070*
C160.3531 (3)0.6740 (3)0.27690 (17)0.0606 (9)
H16A0.36890.71690.25020.073*
C170.2740 (3)0.7106 (3)0.28447 (16)0.0528 (8)
C180.2493 (3)0.6498 (3)0.32446 (17)0.0620 (9)
H18A0.19580.67670.32940.074*
C190.3051 (3)0.5486 (3)0.35685 (18)0.0591 (9)
H19A0.29020.50700.38440.071*
C200.3834 (3)0.5094 (3)0.34818 (17)0.0500 (8)
C210.5136 (3)0.3581 (3)0.37718 (17)0.0560 (9)
H21A0.49290.36750.32850.067*
H21B0.52090.27710.38790.067*
C220.6249 (3)0.4171 (3)0.43298 (17)0.0534 (8)
C230.7331 (3)0.2802 (3)0.4132 (2)0.0615 (10)
C240.8493 (3)0.2430 (3)0.4436 (2)0.0771 (11)
H24A0.84520.18090.41490.116*
H24B0.88860.21850.49350.116*
H24C0.88930.30550.44210.116*
C250.8679 (3)0.3978 (3)0.56963 (19)0.0574 (9)
C260.9615 (3)0.4641 (3)0.6347 (2)0.0828 (11)
H26A0.98210.42860.67890.124*
H26B0.93650.54070.63210.124*
H26C1.02590.46560.63490.124*
C270.8542 (3)0.5358 (3)0.4788 (2)0.0609 (9)
C280.7769 (3)0.5723 (3)0.4003 (2)0.0857 (12)
H28A0.80770.63840.39370.129*
H28B0.70400.59060.38720.129*
H28C0.76930.51160.36970.129*
O10.1627 (3)0.1506 (2)0.30176 (15)0.0978 (10)
O20.2870 (3)0.1469 (3)0.28234 (18)0.1256 (12)
O30.04055 (18)0.59236 (18)0.11342 (13)0.0692 (7)
O4−0.1592 (2)0.50634 (19)0.00605 (13)0.0731 (7)
O5−0.2095 (2)0.79848 (17)0.07476 (13)0.0723 (7)
O6−0.3611 (2)0.6753 (2)−0.12019 (13)0.0814 (8)
O7−0.4705 (2)0.4126 (2)−0.06148 (13)0.0832 (8)
N10.2069 (3)0.1901 (2)0.27528 (17)0.0771 (9)
N2−0.2660 (2)0.62816 (18)0.01591 (13)0.0474 (6)
N3−0.3595 (2)0.56424 (19)−0.03922 (13)0.0491 (6)
C10.0295 (3)0.4494 (3)0.18604 (17)0.0594 (9)
H1A−0.02830.48770.18230.071*
C20.0735 (3)0.3494 (3)0.22626 (17)0.0607 (9)
H2A0.04580.32020.25000.073*
C30.1581 (3)0.2942 (2)0.23061 (17)0.0561 (8)
C40.2002 (3)0.3346 (3)0.19574 (19)0.0661 (10)
H4A0.25740.29540.19930.079*
C50.1565 (3)0.4341 (3)0.15526 (19)0.0633 (9)
H5A0.18350.46200.13080.076*
C60.0724 (3)0.4919 (3)0.15138 (18)0.0547 (8)
C7−0.0556 (3)0.6512 (3)0.09652 (19)0.0608 (9)
H7A−0.05610.72860.08150.073*
H7B−0.05290.65460.13970.073*
C8−0.1609 (3)0.5901 (3)0.03573 (18)0.0528 (8)
C9−0.2871 (3)0.7349 (2)0.03504 (18)0.0523 (8)
C10−0.4056 (3)0.7574 (2)0.00513 (19)0.0625 (9)
H10A−0.41000.82970.02290.094*
H10B−0.43110.69820.02060.094*
H10C−0.45250.7590−0.04750.094*
C11−0.4020 (3)0.5946 (3)−0.11249 (18)0.0591 (9)
C12−0.4949 (3)0.5243 (3)−0.17484 (17)0.0762 (11)
H12A−0.51870.5574−0.22040.114*
H12B−0.55760.5222−0.17330.114*
H12D−0.46810.4481−0.17090.114*
C13−0.3882 (3)0.4682 (2)−0.01662 (19)0.0534 (8)
C14−0.3147 (3)0.4410 (3)0.06307 (18)0.0690 (10)
H14D−0.34700.37890.07170.103*
H14A−0.30880.50680.09010.103*
H14B−0.24080.41990.07890.103*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O80.111 (2)0.0792 (18)0.105 (2)0.0111 (17)0.065 (2)0.0332 (16)
O90.105 (2)0.108 (2)0.131 (3)0.050 (2)0.078 (2)0.0477 (19)
O100.0612 (15)0.0601 (14)0.0769 (16)0.0092 (12)0.0483 (14)0.0163 (12)
O110.0656 (17)0.0729 (15)0.0770 (17)0.0062 (13)0.0390 (15)−0.0271 (14)
O120.093 (2)0.0733 (16)0.116 (2)−0.0312 (16)0.0768 (19)−0.0495 (16)
O130.091 (2)0.0692 (16)0.0765 (18)−0.0022 (15)0.0569 (17)0.0086 (13)
O140.097 (2)0.0708 (17)0.112 (2)−0.0346 (16)0.0712 (19)−0.0268 (16)
N40.072 (2)0.066 (2)0.063 (2)0.0024 (18)0.0335 (19)0.0085 (17)
N50.0546 (17)0.0382 (13)0.0590 (17)−0.0047 (13)0.0381 (15)−0.0102 (12)
N60.0547 (17)0.0396 (13)0.0561 (17)−0.0031 (13)0.0359 (15)−0.0048 (13)
C150.056 (2)0.066 (2)0.059 (2)0.0020 (18)0.039 (2)0.0031 (18)
C160.063 (2)0.064 (2)0.055 (2)−0.0002 (19)0.036 (2)0.0116 (17)
C170.049 (2)0.0513 (19)0.0444 (19)0.0014 (16)0.0213 (18)0.0029 (15)
C180.059 (2)0.074 (2)0.063 (2)0.005 (2)0.042 (2)0.0057 (19)
C190.058 (2)0.067 (2)0.064 (2)0.0060 (19)0.044 (2)0.0117 (18)
C200.047 (2)0.0522 (18)0.0505 (19)−0.0003 (16)0.0300 (18)0.0052 (16)
C210.062 (2)0.0491 (18)0.063 (2)−0.0002 (18)0.042 (2)0.0004 (17)
C220.062 (2)0.0481 (18)0.055 (2)0.0026 (18)0.038 (2)−0.0007 (17)
C230.086 (3)0.0460 (18)0.088 (3)−0.009 (2)0.071 (3)−0.0146 (19)
C240.092 (3)0.0503 (19)0.126 (3)0.000 (2)0.086 (3)−0.012 (2)
C250.055 (2)0.054 (2)0.065 (2)0.0112 (19)0.039 (2)0.0003 (19)
C260.065 (3)0.085 (3)0.065 (2)0.004 (2)0.023 (2)−0.005 (2)
C270.077 (3)0.0436 (19)0.083 (3)−0.0058 (19)0.060 (3)−0.0097 (19)
C280.127 (4)0.049 (2)0.095 (3)0.000 (2)0.075 (3)0.009 (2)
O10.134 (3)0.0697 (18)0.0722 (19)0.0094 (17)0.054 (2)0.0135 (14)
O20.102 (3)0.088 (2)0.149 (3)0.047 (2)0.057 (2)0.0269 (19)
O30.0543 (15)0.0625 (14)0.0942 (18)0.0067 (12)0.0472 (15)0.0271 (13)
O40.0671 (17)0.0672 (15)0.0817 (17)0.0038 (13)0.0438 (15)−0.0129 (14)
O50.0674 (17)0.0409 (12)0.0892 (19)−0.0113 (12)0.0381 (15)−0.0120 (12)
O60.092 (2)0.0794 (17)0.0735 (18)−0.0156 (15)0.0506 (16)0.0125 (14)
O70.088 (2)0.0781 (17)0.0704 (17)−0.0390 (16)0.0414 (16)−0.0145 (14)
N10.079 (3)0.0516 (19)0.064 (2)0.0040 (18)0.025 (2)−0.0032 (16)
N20.0470 (16)0.0364 (13)0.0561 (17)−0.0079 (13)0.0302 (15)−0.0055 (12)
N30.0520 (17)0.0420 (14)0.0482 (16)−0.0049 (13)0.0280 (14)−0.0015 (13)
C10.055 (2)0.0529 (19)0.074 (2)0.0072 (17)0.042 (2)0.0103 (18)
C20.064 (2)0.055 (2)0.058 (2)−0.0022 (19)0.035 (2)0.0048 (17)
C30.056 (2)0.0420 (17)0.051 (2)0.0025 (17)0.0231 (19)−0.0017 (16)
C40.049 (2)0.068 (2)0.070 (2)0.0018 (19)0.030 (2)−0.014 (2)
C50.053 (2)0.066 (2)0.069 (2)0.0009 (19)0.037 (2)0.0060 (19)
C60.042 (2)0.0493 (19)0.062 (2)−0.0029 (16)0.0263 (18)0.0018 (17)
C70.055 (2)0.0425 (17)0.078 (2)−0.0018 (17)0.037 (2)0.0097 (17)
C80.058 (2)0.0446 (18)0.059 (2)−0.0031 (18)0.037 (2)0.0046 (17)
C90.064 (2)0.0340 (16)0.060 (2)−0.0035 (17)0.038 (2)0.0043 (16)
C100.069 (2)0.0477 (18)0.084 (3)−0.0041 (18)0.053 (2)−0.0034 (18)
C110.060 (2)0.059 (2)0.058 (2)0.0089 (19)0.035 (2)0.0037 (19)
C120.086 (3)0.069 (2)0.053 (2)−0.002 (2)0.031 (2)−0.0051 (19)
C130.062 (2)0.0412 (17)0.061 (2)−0.0066 (17)0.039 (2)−0.0028 (17)
C140.077 (3)0.053 (2)0.069 (2)−0.0114 (18)0.041 (2)0.0077 (18)

Geometric parameters (Å, °)

O8—N41.220 (3)O1—N11.232 (4)
O9—N41.224 (4)O2—N11.215 (4)
O10—C201.368 (3)O3—C61.367 (3)
O10—C211.412 (3)O3—C71.418 (3)
O11—C221.203 (3)O4—C81.206 (3)
O12—C231.209 (4)O5—C91.200 (3)
O13—C251.201 (4)O6—C111.197 (4)
O14—C271.200 (4)O7—C131.204 (3)
N4—C171.463 (4)N1—C31.471 (4)
N5—N61.402 (3)N2—N31.398 (3)
N5—C231.407 (4)N2—C81.414 (4)
N5—C221.415 (4)N2—C91.424 (4)
N6—C271.408 (4)N3—C131.413 (3)
N6—C251.433 (4)N3—C111.437 (4)
C15—C201.384 (4)C1—C21.385 (4)
C15—C161.387 (4)C1—C61.386 (4)
C15—H15A0.9300C1—H1A0.9300
C16—C171.365 (4)C2—C31.370 (4)
C16—H16A0.9300C2—H2A0.9300
C17—C181.382 (4)C3—C41.372 (4)
C18—C191.377 (4)C4—C51.383 (4)
C18—H18A0.9300C4—H4A0.9300
C19—C201.380 (4)C5—C61.382 (4)
C19—H19A0.9300C5—H5A0.9300
C21—C221.511 (4)C7—C81.501 (4)
C21—H21A0.9700C7—H7A0.9700
C21—H21B0.9700C7—H7B0.9700
C23—C241.486 (4)C9—C101.479 (4)
C24—H24A0.9600C10—H10A0.9600
C24—H24B0.9600C10—H10B0.9600
C24—H24C0.9600C10—H10C0.9600
C25—C261.497 (5)C11—C121.493 (4)
C26—H26A0.9600C12—H12A0.9600
C26—H26B0.9600C12—H12B0.9600
C26—H26C0.9600C12—H12D0.9600
C27—C281.494 (5)C13—C141.487 (4)
C28—H28A0.9600C14—H14D0.9600
C28—H28B0.9600C14—H14A0.9600
C28—H28C0.9600C14—H14B0.9600
Cg1···Cg23.722 (5)
C20—O10—C21119.9 (2)C6—O3—C7119.5 (2)
O8—N4—O9123.3 (3)O2—N1—O1124.1 (4)
O8—N4—C17118.3 (3)O2—N1—C3117.8 (4)
O9—N4—C17118.4 (3)O1—N1—C3118.1 (4)
N6—N5—C23118.2 (3)N3—N2—C8114.8 (2)
N6—N5—C22114.0 (2)N3—N2—C9117.7 (2)
C23—N5—C22125.6 (3)C8—N2—C9126.1 (3)
N5—N6—C27118.0 (3)N2—N3—C13116.9 (2)
N5—N6—C25113.6 (2)N2—N3—C11114.3 (2)
C27—N6—C25127.6 (3)C13—N3—C11127.9 (3)
C20—C15—C16119.2 (3)C2—C1—C6119.5 (3)
C20—C15—H15A120.4C2—C1—H1A120.3
C16—C15—H15A120.4C6—C1—H1A120.3
C17—C16—C15119.2 (3)C3—C2—C1119.2 (3)
C17—C16—H16A120.4C3—C2—H2A120.4
C15—C16—H16A120.4C1—C2—H2A120.4
C16—C17—C18121.9 (3)C2—C3—C4121.9 (3)
C16—C17—N4119.5 (3)C2—C3—N1119.0 (3)
C18—C17—N4118.6 (3)C4—C3—N1119.2 (3)
C19—C18—C17119.0 (3)C3—C4—C5119.3 (3)
C19—C18—H18A120.5C3—C4—H4A120.3
C17—C18—H18A120.5C5—C4—H4A120.3
C18—C19—C20119.6 (3)C6—C5—C4119.5 (3)
C18—C19—H19A120.2C6—C5—H5A120.2
C20—C19—H19A120.2C4—C5—H5A120.2
O10—C20—C19114.4 (3)O3—C6—C5114.2 (3)
O10—C20—C15124.6 (3)O3—C6—C1125.1 (3)
C19—C20—C15121.0 (3)C5—C6—C1120.6 (3)
O10—C21—C22109.8 (2)O3—C7—C8109.4 (3)
O10—C21—H21A109.7O3—C7—H7A109.8
C22—C21—H21A109.7C8—C7—H7A109.8
O10—C21—H21B109.7O3—C7—H7B109.8
C22—C21—H21B109.7C8—C7—H7B109.8
H21A—C21—H21B108.2H7A—C7—H7B108.2
O11—C22—N5118.9 (3)O4—C8—N2118.6 (3)
O11—C22—C21121.8 (3)O4—C8—C7123.0 (3)
N5—C22—C21119.3 (3)N2—C8—C7118.3 (3)
O12—C23—N5118.8 (3)O5—C9—N2119.2 (3)
O12—C23—C24124.0 (3)O5—C9—C10124.6 (3)
N5—C23—C24117.2 (3)N2—C9—C10116.2 (3)
C23—C24—H24A109.5C9—C10—H10A109.5
C23—C24—H24B109.5C9—C10—H10B109.5
H24A—C24—H24B109.5H10A—C10—H10B109.5
C23—C24—H24C109.5C9—C10—H10C109.5
H24A—C24—H24C109.5H10A—C10—H10C109.5
H24B—C24—H24C109.5H10B—C10—H10C109.5
O13—C25—N6117.9 (3)O6—C11—N3118.1 (3)
O13—C25—C26123.4 (3)O6—C11—C12123.5 (3)
N6—C25—C26118.8 (3)N3—C11—C12118.4 (3)
C25—C26—H26A109.5C11—C12—H12A109.5
C25—C26—H26B109.5C11—C12—H12B109.5
H26A—C26—H26B109.5H12A—C12—H12B109.5
C25—C26—H26C109.5C11—C12—H12D109.5
H26A—C26—H26C109.5H12A—C12—H12D109.5
H26B—C26—H26C109.5H12B—C12—H12D109.5
O14—C27—N6119.7 (3)O7—C13—N3119.8 (3)
O14—C27—C28123.7 (3)O7—C13—C14122.6 (3)
N6—C27—C28116.6 (3)N3—C13—C14117.6 (3)
C27—C28—H28A109.5C13—C14—H14D109.5
C27—C28—H28B109.5C13—C14—H14A109.5
H28A—C28—H28B109.5H14D—C14—H14A109.5
C27—C28—H28C109.5C13—C14—H14B109.5
H28A—C28—H28C109.5H14D—C14—H14B109.5
H28B—C28—H28C109.5H14A—C14—H14B109.5
C23—N5—N6—C27102.4 (3)C8—N2—N3—C1387.8 (3)
C22—N5—N6—C27−93.4 (3)C9—N2—N3—C13−104.8 (3)
C23—N5—N6—C25−86.8 (3)C8—N2—N3—C11−82.3 (3)
C22—N5—N6—C2577.4 (3)C9—N2—N3—C1185.1 (3)
C20—C15—C16—C170.8 (5)C6—C1—C2—C3−0.4 (5)
C15—C16—C17—C180.8 (5)C1—C2—C3—C4−0.5 (5)
C15—C16—C17—N4−177.6 (3)C1—C2—C3—N1178.1 (3)
O8—N4—C17—C16−1.7 (5)O2—N1—C3—C2−175.2 (3)
O9—N4—C17—C16176.6 (3)O1—N1—C3—C26.5 (5)
O8—N4—C17—C18179.9 (3)O2—N1—C3—C43.5 (5)
O9—N4—C17—C18−1.8 (5)O1—N1—C3—C4−174.8 (3)
C16—C17—C18—C19−0.8 (5)C2—C3—C4—C50.3 (5)
N4—C17—C18—C19177.5 (3)N1—C3—C4—C5−178.3 (3)
C17—C18—C19—C20−0.7 (5)C3—C4—C5—C60.8 (5)
C21—O10—C20—C19−177.0 (3)C7—O3—C6—C5171.0 (3)
C21—O10—C20—C154.4 (4)C7—O3—C6—C1−11.1 (5)
C18—C19—C20—O10−176.4 (3)C4—C5—C6—O3176.4 (3)
C18—C19—C20—C152.3 (5)C4—C5—C6—C1−1.7 (5)
C16—C15—C20—O10176.2 (3)C2—C1—C6—O3−176.4 (3)
C16—C15—C20—C19−2.3 (5)C2—C1—C6—C51.5 (5)
C20—O10—C21—C2275.9 (3)C6—O3—C7—C8−74.3 (3)
N6—N5—C22—O115.7 (4)N3—N2—C8—O4−1.9 (4)
C23—N5—C22—O11168.5 (3)C9—N2—C8—O4−168.2 (3)
N6—N5—C22—C21−176.6 (2)N3—N2—C8—C7−177.7 (2)
C23—N5—C22—C21−13.8 (4)C9—N2—C8—C716.1 (4)
O10—C21—C22—O11−3.7 (4)O3—C7—C8—O4−2.3 (4)
O10—C21—C22—N5178.7 (2)O3—C7—C8—N2173.3 (2)
N6—N5—C23—O12179.3 (3)N3—N2—C9—O5−170.1 (2)
C22—N5—C23—O1217.1 (5)C8—N2—C9—O5−4.2 (4)
N6—N5—C23—C24−2.2 (4)N3—N2—C9—C1011.6 (4)
C22—N5—C23—C24−164.4 (3)C8—N2—C9—C10177.5 (3)
N5—N6—C25—O1310.5 (4)N2—N3—C11—O6−5.7 (4)
C27—N6—C25—O13−179.8 (3)C13—N3—C11—O6−174.6 (3)
N5—N6—C25—C26−169.5 (3)N2—N3—C11—C12174.5 (3)
C27—N6—C25—C260.3 (4)C13—N3—C11—C125.7 (4)
N5—N6—C27—O14−177.0 (3)N2—N3—C13—O7177.2 (3)
C25—N6—C27—O1413.7 (5)C11—N3—C13—O7−14.3 (5)
N5—N6—C27—C282.0 (4)N2—N3—C13—C14−2.1 (4)
C25—N6—C27—C28−167.4 (3)C11—N3—C13—C14166.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···O12i0.932.523.328 (4)146
C18—H18A···O13ii0.932.463.214 (4)138
C21—H21B···O7iii0.972.483.422 (4)165
C24—H24A···O3iv0.962.413.194 (4)139
C28—H28C···O8iv0.962.513.465 (4)172
C24—H24C···O14v0.962.523.423 (4)157
C26—H26B···O5vi0.962.563.444 (4)154
C10—H10B···O7vii0.962.543.469 (4)164
C12—H12D···O12viii0.962.513.450 (4)166

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x+1, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) −x+2, −y+1, −z+1; (vi) x+1, −y+3/2, z+1/2; (vii) −x−1, −y+1, −z; (viii) x−1, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2509).

References

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  • Liras, S., Allen, M. P. & Segelstein, B. (2000). Synth. Commun.30, 437–443.
  • Lutun, S., Hasiak, B. & Couturier, D. (1999). Synth. Commun.29, 111–116.
  • Pang, D. M., Wang, H. T. & Li, M. (2005). Tetrahedron, 61, 6108–6114.
  • Rigaku. (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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