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

Hu, X.; Wang, Z.; Xu, W.; Zhao, G.; Wang, R.

doi:10.1107/S1600536809002232

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o372

doi:10.1107/S1600536809002232

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

Xiao Hu,^a Zhifeng Wang,^b Weiren Xu,^b Guilong Zhao ^b and Runling Wang ^a ^*

^aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: wangrunling2008@yahoo.cn

(Received 6 January 2009; accepted 16 January 2009; online 23 January 2009)

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 ); Lutun et al. (1999 ); Liras et al. (2000 ); Dhadialla et al. (1998 ).

Experimental

Crystal data

C₁₄H₁₅N₃O₇
M_r = 337.29
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.152
S = 0.90
5619 reflections
439 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected interatomic distances (Å)

Cg1 and Cg2 are the centroids of the rings C1–C6 and C15–C20, respectively.

Cg1⋯Cg2	3.722 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O12ⁱ	0.93	2.52	3.328 (4)	146
C18—H18A⋯O13ⁱⁱ	0.93	2.46	3.214 (4)	138
C21—H21B⋯O7ⁱⁱⁱ	0.97	2.48	3.422 (4)	165
C24—H24A⋯O3^iv	0.96	2.41	3.194 (4)	139
C28—H28C⋯O8^iv	0.96	2.51	3.465 (4)	172
C24—H24C⋯O14^v	0.96	2.52	3.423 (4)	157
C26—H26B⋯O5^vi	0.96	2.56	3.444 (4)	154
C10—H10B⋯O7^vii	0.96	2.54	3.469 (4)	164
C12—H12D⋯O12^viii	0.96	2.51	3.450 (4)	166
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+2, -y+1, -z+1; (vi) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vii) -x-1, -y+1, -z; (viii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

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

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

Crystal data top

C₁₄H₁₅N₃O₇	F(000) = 1408
M_r = 337.29	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5002 reflections
a = 14.949 (3) Å	θ = 1.7–27.7°
b = 11.723 (2) Å	µ = 0.11 mm⁻¹
c = 23.034 (7) Å	T = 113 K
β = 127.73 (2)°	Block, yellow
V = 3192.6 (15) Å³	0.28 × 0.24 × 0.18 mm
Z = 8

Data collection top

Rigaku Saturn diffractometer	5619 independent reflections
Radiation source: rotating anode	2699 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.082
ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −16→17
T_min = 0.969, T_max = 0.980	k = −13→13
21295 measured reflections	l = −25→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0651P)²] where P = (F_o² + 2F_c²)/3
5619 reflections	(Δ/σ)_max = 0.001
439 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₅N₃O₇	V = 3192.6 (15) Å³
M_r = 337.29	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.949 (3) Å	µ = 0.11 mm⁻¹
b = 11.723 (2) Å	T = 113 K
c = 23.034 (7) Å	0.28 × 0.24 × 0.18 mm
β = 127.73 (2)°

Data collection top

Rigaku Saturn diffractometer	5619 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2699 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.980	R_int = 0.082
21295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 0.90	Δρ_max = 0.19 e Å⁻³
5619 reflections	Δρ_min = −0.24 e Å⁻³
439 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

	x	y	z	U_iso*/U_eq
O8	0.2333 (2)	0.8689 (2)	0.21267 (15)	0.0989 (9)
O9	0.1368 (3)	0.8437 (2)	0.25247 (17)	0.1111 (11)
O10	0.42854 (18)	0.40509 (18)	0.37921 (12)	0.0621 (6)
O11	0.6321 (2)	0.49597 (19)	0.46900 (13)	0.0748 (7)
O12	0.6482 (2)	0.2300 (2)	0.36527 (15)	0.0855 (8)
O13	0.8291 (2)	0.3120 (2)	0.57451 (13)	0.0753 (7)
O14	0.9409 (3)	0.5835 (2)	0.52505 (16)	0.0881 (8)
N4	0.2110 (3)	0.8155 (2)	0.24781 (17)	0.0722 (8)
N5	0.7227 (2)	0.38153 (19)	0.44137 (13)	0.0484 (6)
N6	0.8218 (2)	0.43821 (19)	0.49755 (14)	0.0488 (6)
C15	0.4096 (3)	0.5723 (3)	0.30951 (17)	0.0579 (9)
H15A	0.4643	0.5466	0.3054	0.070*
C16	0.3531 (3)	0.6740 (3)	0.27690 (17)	0.0606 (9)
H16A	0.3689	0.7169	0.2502	0.073*
C17	0.2740 (3)	0.7106 (3)	0.28447 (16)	0.0528 (8)
C18	0.2493 (3)	0.6498 (3)	0.32446 (17)	0.0620 (9)
H18A	0.1958	0.6767	0.3294	0.074*
C19	0.3051 (3)	0.5486 (3)	0.35685 (18)	0.0591 (9)
H19A	0.2902	0.5070	0.3844	0.071*
C20	0.3834 (3)	0.5094 (3)	0.34818 (17)	0.0500 (8)
C21	0.5136 (3)	0.3581 (3)	0.37718 (17)	0.0560 (9)
H21A	0.4929	0.3675	0.3285	0.067*
H21B	0.5209	0.2771	0.3879	0.067*
C22	0.6249 (3)	0.4171 (3)	0.43298 (17)	0.0534 (8)
C23	0.7331 (3)	0.2802 (3)	0.4132 (2)	0.0615 (10)
C24	0.8493 (3)	0.2430 (3)	0.4436 (2)	0.0771 (11)
H24A	0.8452	0.1809	0.4149	0.116*
H24B	0.8886	0.2185	0.4935	0.116*
H24C	0.8893	0.3055	0.4421	0.116*
C25	0.8679 (3)	0.3978 (3)	0.56963 (19)	0.0574 (9)
C26	0.9615 (3)	0.4641 (3)	0.6347 (2)	0.0828 (11)
H26A	0.9821	0.4286	0.6789	0.124*
H26B	0.9365	0.5407	0.6321	0.124*
H26C	1.0259	0.4656	0.6349	0.124*
C27	0.8542 (3)	0.5358 (3)	0.4788 (2)	0.0609 (9)
C28	0.7769 (3)	0.5723 (3)	0.4003 (2)	0.0857 (12)
H28A	0.8077	0.6384	0.3937	0.129*
H28B	0.7040	0.5906	0.3872	0.129*
H28C	0.7693	0.5116	0.3697	0.129*
O1	0.1627 (3)	0.1506 (2)	0.30176 (15)	0.0978 (10)
O2	0.2870 (3)	0.1469 (3)	0.28234 (18)	0.1256 (12)
O3	0.04055 (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)
N1	0.2069 (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)
C1	0.0295 (3)	0.4494 (3)	0.18604 (17)	0.0594 (9)
H1A	−0.0283	0.4877	0.1823	0.071*
C2	0.0735 (3)	0.3494 (3)	0.22626 (17)	0.0607 (9)
H2A	0.0458	0.3202	0.2500	0.073*
C3	0.1581 (3)	0.2942 (2)	0.23061 (17)	0.0561 (8)
C4	0.2002 (3)	0.3346 (3)	0.19574 (19)	0.0661 (10)
H4A	0.2574	0.2954	0.1993	0.079*
C5	0.1565 (3)	0.4341 (3)	0.15526 (19)	0.0633 (9)
H5A	0.1835	0.4620	0.1308	0.076*
C6	0.0724 (3)	0.4919 (3)	0.15138 (18)	0.0547 (8)
C7	−0.0556 (3)	0.6512 (3)	0.09652 (19)	0.0608 (9)
H7A	−0.0561	0.7286	0.0815	0.073*
H7B	−0.0529	0.6546	0.1397	0.073*
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	−0.4100	0.8297	0.0229	0.094*
H10B	−0.4311	0.6982	0.0206	0.094*
H10C	−0.4525	0.7590	−0.0475	0.094*
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	−0.5187	0.5574	−0.2204	0.114*
H12B	−0.5576	0.5222	−0.1733	0.114*
H12D	−0.4681	0.4481	−0.1709	0.114*
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	−0.3470	0.3789	0.0717	0.103*
H14A	−0.3088	0.5068	0.0901	0.103*
H14B	−0.2408	0.4199	0.0789	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O8	0.111 (2)	0.0792 (18)	0.105 (2)	0.0111 (17)	0.065 (2)	0.0332 (16)
O9	0.105 (2)	0.108 (2)	0.131 (3)	0.050 (2)	0.078 (2)	0.0477 (19)
O10	0.0612 (15)	0.0601 (14)	0.0769 (16)	0.0092 (12)	0.0483 (14)	0.0163 (12)
O11	0.0656 (17)	0.0729 (15)	0.0770 (17)	0.0062 (13)	0.0390 (15)	−0.0271 (14)
O12	0.093 (2)	0.0733 (16)	0.116 (2)	−0.0312 (16)	0.0768 (19)	−0.0495 (16)
O13	0.091 (2)	0.0692 (16)	0.0765 (18)	−0.0022 (15)	0.0569 (17)	0.0086 (13)
O14	0.097 (2)	0.0708 (17)	0.112 (2)	−0.0346 (16)	0.0712 (19)	−0.0268 (16)
N4	0.072 (2)	0.066 (2)	0.063 (2)	0.0024 (18)	0.0335 (19)	0.0085 (17)
N5	0.0546 (17)	0.0382 (13)	0.0590 (17)	−0.0047 (13)	0.0381 (15)	−0.0102 (12)
N6	0.0547 (17)	0.0396 (13)	0.0561 (17)	−0.0031 (13)	0.0359 (15)	−0.0048 (13)
C15	0.056 (2)	0.066 (2)	0.059 (2)	0.0020 (18)	0.039 (2)	0.0031 (18)
C16	0.063 (2)	0.064 (2)	0.055 (2)	−0.0002 (19)	0.036 (2)	0.0116 (17)
C17	0.049 (2)	0.0513 (19)	0.0444 (19)	0.0014 (16)	0.0213 (18)	0.0029 (15)
C18	0.059 (2)	0.074 (2)	0.063 (2)	0.005 (2)	0.042 (2)	0.0057 (19)
C19	0.058 (2)	0.067 (2)	0.064 (2)	0.0060 (19)	0.044 (2)	0.0117 (18)
C20	0.047 (2)	0.0522 (18)	0.0505 (19)	−0.0003 (16)	0.0300 (18)	0.0052 (16)
C21	0.062 (2)	0.0491 (18)	0.063 (2)	−0.0002 (18)	0.042 (2)	0.0004 (17)
C22	0.062 (2)	0.0481 (18)	0.055 (2)	0.0026 (18)	0.038 (2)	−0.0007 (17)
C23	0.086 (3)	0.0460 (18)	0.088 (3)	−0.009 (2)	0.071 (3)	−0.0146 (19)
C24	0.092 (3)	0.0503 (19)	0.126 (3)	0.000 (2)	0.086 (3)	−0.012 (2)
C25	0.055 (2)	0.054 (2)	0.065 (2)	0.0112 (19)	0.039 (2)	0.0003 (19)
C26	0.065 (3)	0.085 (3)	0.065 (2)	0.004 (2)	0.023 (2)	−0.005 (2)
C27	0.077 (3)	0.0436 (19)	0.083 (3)	−0.0058 (19)	0.060 (3)	−0.0097 (19)
C28	0.127 (4)	0.049 (2)	0.095 (3)	0.000 (2)	0.075 (3)	0.009 (2)
O1	0.134 (3)	0.0697 (18)	0.0722 (19)	0.0094 (17)	0.054 (2)	0.0135 (14)
O2	0.102 (3)	0.088 (2)	0.149 (3)	0.047 (2)	0.057 (2)	0.0269 (19)
O3	0.0543 (15)	0.0625 (14)	0.0942 (18)	0.0067 (12)	0.0472 (15)	0.0271 (13)
O4	0.0671 (17)	0.0672 (15)	0.0817 (17)	0.0038 (13)	0.0438 (15)	−0.0129 (14)
O5	0.0674 (17)	0.0409 (12)	0.0892 (19)	−0.0113 (12)	0.0381 (15)	−0.0120 (12)
O6	0.092 (2)	0.0794 (17)	0.0735 (18)	−0.0156 (15)	0.0506 (16)	0.0125 (14)
O7	0.088 (2)	0.0781 (17)	0.0704 (17)	−0.0390 (16)	0.0414 (16)	−0.0145 (14)
N1	0.079 (3)	0.0516 (19)	0.064 (2)	0.0040 (18)	0.025 (2)	−0.0032 (16)
N2	0.0470 (16)	0.0364 (13)	0.0561 (17)	−0.0079 (13)	0.0302 (15)	−0.0055 (12)
N3	0.0520 (17)	0.0420 (14)	0.0482 (16)	−0.0049 (13)	0.0280 (14)	−0.0015 (13)
C1	0.055 (2)	0.0529 (19)	0.074 (2)	0.0072 (17)	0.042 (2)	0.0103 (18)
C2	0.064 (2)	0.055 (2)	0.058 (2)	−0.0022 (19)	0.035 (2)	0.0048 (17)
C3	0.056 (2)	0.0420 (17)	0.051 (2)	0.0025 (17)	0.0231 (19)	−0.0017 (16)
C4	0.049 (2)	0.068 (2)	0.070 (2)	0.0018 (19)	0.030 (2)	−0.014 (2)
C5	0.053 (2)	0.066 (2)	0.069 (2)	0.0009 (19)	0.037 (2)	0.0060 (19)
C6	0.042 (2)	0.0493 (19)	0.062 (2)	−0.0029 (16)	0.0263 (18)	0.0018 (17)
C7	0.055 (2)	0.0425 (17)	0.078 (2)	−0.0018 (17)	0.037 (2)	0.0097 (17)
C8	0.058 (2)	0.0446 (18)	0.059 (2)	−0.0031 (18)	0.037 (2)	0.0046 (17)
C9	0.064 (2)	0.0340 (16)	0.060 (2)	−0.0035 (17)	0.038 (2)	0.0043 (16)
C10	0.069 (2)	0.0477 (18)	0.084 (3)	−0.0041 (18)	0.053 (2)	−0.0034 (18)
C11	0.060 (2)	0.059 (2)	0.058 (2)	0.0089 (19)	0.035 (2)	0.0037 (19)
C12	0.086 (3)	0.069 (2)	0.053 (2)	−0.002 (2)	0.031 (2)	−0.0051 (19)
C13	0.062 (2)	0.0412 (17)	0.061 (2)	−0.0066 (17)	0.039 (2)	−0.0028 (17)
C14	0.077 (3)	0.053 (2)	0.069 (2)	−0.0114 (18)	0.041 (2)	0.0077 (18)

Geometric parameters (Å, º) top

O8—N4	1.220 (3)	O1—N1	1.232 (4)
O9—N4	1.224 (4)	O2—N1	1.215 (4)
O10—C20	1.368 (3)	O3—C6	1.367 (3)
O10—C21	1.412 (3)	O3—C7	1.418 (3)
O11—C22	1.203 (3)	O4—C8	1.206 (3)
O12—C23	1.209 (4)	O5—C9	1.200 (3)
O13—C25	1.201 (4)	O6—C11	1.197 (4)
O14—C27	1.200 (4)	O7—C13	1.204 (3)
N4—C17	1.463 (4)	N1—C3	1.471 (4)
N5—N6	1.402 (3)	N2—N3	1.398 (3)
N5—C23	1.407 (4)	N2—C8	1.414 (4)
N5—C22	1.415 (4)	N2—C9	1.424 (4)
N6—C27	1.408 (4)	N3—C13	1.413 (3)
N6—C25	1.433 (4)	N3—C11	1.437 (4)
C15—C20	1.384 (4)	C1—C2	1.385 (4)
C15—C16	1.387 (4)	C1—C6	1.386 (4)
C15—H15A	0.9300	C1—H1A	0.9300
C16—C17	1.365 (4)	C2—C3	1.370 (4)
C16—H16A	0.9300	C2—H2A	0.9300
C17—C18	1.382 (4)	C3—C4	1.372 (4)
C18—C19	1.377 (4)	C4—C5	1.383 (4)
C18—H18A	0.9300	C4—H4A	0.9300
C19—C20	1.380 (4)	C5—C6	1.382 (4)
C19—H19A	0.9300	C5—H5A	0.9300
C21—C22	1.511 (4)	C7—C8	1.501 (4)
C21—H21A	0.9700	C7—H7A	0.9700
C21—H21B	0.9700	C7—H7B	0.9700
C23—C24	1.486 (4)	C9—C10	1.479 (4)
C24—H24A	0.9600	C10—H10A	0.9600
C24—H24B	0.9600	C10—H10B	0.9600
C24—H24C	0.9600	C10—H10C	0.9600
C25—C26	1.497 (5)	C11—C12	1.493 (4)
C26—H26A	0.9600	C12—H12A	0.9600
C26—H26B	0.9600	C12—H12B	0.9600
C26—H26C	0.9600	C12—H12D	0.9600
C27—C28	1.494 (5)	C13—C14	1.487 (4)
C28—H28A	0.9600	C14—H14D	0.9600
C28—H28B	0.9600	C14—H14A	0.9600
C28—H28C	0.9600	C14—H14B	0.9600

Cg1···Cg2	3.722 (5)

C20—O10—C21	119.9 (2)	C6—O3—C7	119.5 (2)
O8—N4—O9	123.3 (3)	O2—N1—O1	124.1 (4)
O8—N4—C17	118.3 (3)	O2—N1—C3	117.8 (4)
O9—N4—C17	118.4 (3)	O1—N1—C3	118.1 (4)
N6—N5—C23	118.2 (3)	N3—N2—C8	114.8 (2)
N6—N5—C22	114.0 (2)	N3—N2—C9	117.7 (2)
C23—N5—C22	125.6 (3)	C8—N2—C9	126.1 (3)
N5—N6—C27	118.0 (3)	N2—N3—C13	116.9 (2)
N5—N6—C25	113.6 (2)	N2—N3—C11	114.3 (2)
C27—N6—C25	127.6 (3)	C13—N3—C11	127.9 (3)
C20—C15—C16	119.2 (3)	C2—C1—C6	119.5 (3)
C20—C15—H15A	120.4	C2—C1—H1A	120.3
C16—C15—H15A	120.4	C6—C1—H1A	120.3
C17—C16—C15	119.2 (3)	C3—C2—C1	119.2 (3)
C17—C16—H16A	120.4	C3—C2—H2A	120.4
C15—C16—H16A	120.4	C1—C2—H2A	120.4
C16—C17—C18	121.9 (3)	C2—C3—C4	121.9 (3)
C16—C17—N4	119.5 (3)	C2—C3—N1	119.0 (3)
C18—C17—N4	118.6 (3)	C4—C3—N1	119.2 (3)
C19—C18—C17	119.0 (3)	C3—C4—C5	119.3 (3)
C19—C18—H18A	120.5	C3—C4—H4A	120.3
C17—C18—H18A	120.5	C5—C4—H4A	120.3
C18—C19—C20	119.6 (3)	C6—C5—C4	119.5 (3)
C18—C19—H19A	120.2	C6—C5—H5A	120.2
C20—C19—H19A	120.2	C4—C5—H5A	120.2
O10—C20—C19	114.4 (3)	O3—C6—C5	114.2 (3)
O10—C20—C15	124.6 (3)	O3—C6—C1	125.1 (3)
C19—C20—C15	121.0 (3)	C5—C6—C1	120.6 (3)
O10—C21—C22	109.8 (2)	O3—C7—C8	109.4 (3)
O10—C21—H21A	109.7	O3—C7—H7A	109.8
C22—C21—H21A	109.7	C8—C7—H7A	109.8
O10—C21—H21B	109.7	O3—C7—H7B	109.8
C22—C21—H21B	109.7	C8—C7—H7B	109.8
H21A—C21—H21B	108.2	H7A—C7—H7B	108.2
O11—C22—N5	118.9 (3)	O4—C8—N2	118.6 (3)
O11—C22—C21	121.8 (3)	O4—C8—C7	123.0 (3)
N5—C22—C21	119.3 (3)	N2—C8—C7	118.3 (3)
O12—C23—N5	118.8 (3)	O5—C9—N2	119.2 (3)
O12—C23—C24	124.0 (3)	O5—C9—C10	124.6 (3)
N5—C23—C24	117.2 (3)	N2—C9—C10	116.2 (3)
C23—C24—H24A	109.5	C9—C10—H10A	109.5
C23—C24—H24B	109.5	C9—C10—H10B	109.5
H24A—C24—H24B	109.5	H10A—C10—H10B	109.5
C23—C24—H24C	109.5	C9—C10—H10C	109.5
H24A—C24—H24C	109.5	H10A—C10—H10C	109.5
H24B—C24—H24C	109.5	H10B—C10—H10C	109.5
O13—C25—N6	117.9 (3)	O6—C11—N3	118.1 (3)
O13—C25—C26	123.4 (3)	O6—C11—C12	123.5 (3)
N6—C25—C26	118.8 (3)	N3—C11—C12	118.4 (3)
C25—C26—H26A	109.5	C11—C12—H12A	109.5
C25—C26—H26B	109.5	C11—C12—H12B	109.5
H26A—C26—H26B	109.5	H12A—C12—H12B	109.5
C25—C26—H26C	109.5	C11—C12—H12D	109.5
H26A—C26—H26C	109.5	H12A—C12—H12D	109.5
H26B—C26—H26C	109.5	H12B—C12—H12D	109.5
O14—C27—N6	119.7 (3)	O7—C13—N3	119.8 (3)
O14—C27—C28	123.7 (3)	O7—C13—C14	122.6 (3)
N6—C27—C28	116.6 (3)	N3—C13—C14	117.6 (3)
C27—C28—H28A	109.5	C13—C14—H14D	109.5
C27—C28—H28B	109.5	C13—C14—H14A	109.5
H28A—C28—H28B	109.5	H14D—C14—H14A	109.5
C27—C28—H28C	109.5	C13—C14—H14B	109.5
H28A—C28—H28C	109.5	H14D—C14—H14B	109.5
H28B—C28—H28C	109.5	H14A—C14—H14B	109.5

C23—N5—N6—C27	102.4 (3)	C8—N2—N3—C13	87.8 (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—C25	77.4 (3)	C9—N2—N3—C11	85.1 (3)
C20—C15—C16—C17	0.8 (5)	C6—C1—C2—C3	−0.4 (5)
C15—C16—C17—C18	0.8 (5)	C1—C2—C3—C4	−0.5 (5)
C15—C16—C17—N4	−177.6 (3)	C1—C2—C3—N1	178.1 (3)
O8—N4—C17—C16	−1.7 (5)	O2—N1—C3—C2	−175.2 (3)
O9—N4—C17—C16	176.6 (3)	O1—N1—C3—C2	6.5 (5)
O8—N4—C17—C18	179.9 (3)	O2—N1—C3—C4	3.5 (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—C5	0.3 (5)
N4—C17—C18—C19	177.5 (3)	N1—C3—C4—C5	−178.3 (3)
C17—C18—C19—C20	−0.7 (5)	C3—C4—C5—C6	0.8 (5)
C21—O10—C20—C19	−177.0 (3)	C7—O3—C6—C5	171.0 (3)
C21—O10—C20—C15	4.4 (4)	C7—O3—C6—C1	−11.1 (5)
C18—C19—C20—O10	−176.4 (3)	C4—C5—C6—O3	176.4 (3)
C18—C19—C20—C15	2.3 (5)	C4—C5—C6—C1	−1.7 (5)
C16—C15—C20—O10	176.2 (3)	C2—C1—C6—O3	−176.4 (3)
C16—C15—C20—C19	−2.3 (5)	C2—C1—C6—C5	1.5 (5)
C20—O10—C21—C22	75.9 (3)	C6—O3—C7—C8	−74.3 (3)
N6—N5—C22—O11	5.7 (4)	N3—N2—C8—O4	−1.9 (4)
C23—N5—C22—O11	168.5 (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—C7	16.1 (4)
O10—C21—C22—O11	−3.7 (4)	O3—C7—C8—O4	−2.3 (4)
O10—C21—C22—N5	178.7 (2)	O3—C7—C8—N2	173.3 (2)
N6—N5—C23—O12	179.3 (3)	N3—N2—C9—O5	−170.1 (2)
C22—N5—C23—O12	17.1 (5)	C8—N2—C9—O5	−4.2 (4)
N6—N5—C23—C24	−2.2 (4)	N3—N2—C9—C10	11.6 (4)
C22—N5—C23—C24	−164.4 (3)	C8—N2—C9—C10	177.5 (3)
N5—N6—C25—O13	10.5 (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—C12	174.5 (3)
C27—N6—C25—C26	0.3 (4)	C13—N3—C11—C12	5.7 (4)
N5—N6—C27—O14	−177.0 (3)	N2—N3—C13—O7	177.2 (3)
C25—N6—C27—O14	13.7 (5)	C11—N3—C13—O7	−14.3 (5)
N5—N6—C27—C28	2.0 (4)	N2—N3—C13—C14	−2.1 (4)
C25—N6—C27—C28	−167.4 (3)	C11—N3—C13—C14	166.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O12ⁱ	0.93	2.52	3.328 (4)	146
C18—H18A···O13ⁱⁱ	0.93	2.46	3.214 (4)	138
C21—H21B···O7ⁱⁱⁱ	0.97	2.48	3.422 (4)	165
C24—H24A···O3^iv	0.96	2.41	3.194 (4)	139
C28—H28C···O8^iv	0.96	2.51	3.465 (4)	172
C24—H24C···O14^v	0.96	2.52	3.423 (4)	157
C26—H26B···O5^vi	0.96	2.56	3.444 (4)	154
C10—H10B···O7^vii	0.96	2.54	3.469 (4)	164
C12—H12D···O12^viii	0.96	2.51	3.450 (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.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃O₇
M_r	337.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	14.949 (3), 11.723 (2), 23.034 (7)
β (°)	127.73 (2)
V (Å³)	3192.6 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.28 × 0.24 × 0.18

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.969, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	21295, 5619, 2699
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.152, 0.90
No. of reflections	5619
No. of parameters	439
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg2

3.722 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O12ⁱ	0.93	2.52	3.328 (4)	146.1
C18—H18A···O13ⁱⁱ	0.93	2.46	3.214 (4)	138.0
C21—H21B···O7ⁱⁱⁱ	0.97	2.48	3.422 (4)	164.5
C24—H24A···O3^iv	0.96	2.41	3.194 (4)	139.2
C28—H28C···O8^iv	0.96	2.51	3.465 (4)	172.1
C24—H24C···O14^v	0.96	2.52	3.423 (4)	156.6
C26—H26B···O5^vi	0.96	2.56	3.444 (4)	154.0
C10—H10B···O7^vii	0.96	2.54	3.469 (4)	164.0
C12—H12D···O12^viii	0.96	2.51	3.450 (4)	165.8

References

Dhadialla, T. S., Carlson, G. R. & Le, D. P. (1998). Annu. Rev. Entomol. 43, 545–569. Web of Science CrossRef CAS PubMed Google Scholar
Liras, S., Allen, M. P. & Segelstein, B. (2000). Synth. Commun. 30, 437–443. Web of Science CrossRef CAS Google Scholar
Lutun, S., Hasiak, B. & Couturier, D. (1999). Synth. Commun. 29, 111–116. Web of Science CrossRef CAS Google Scholar
Pang, D. M., Wang, H. T. & Li, M. (2005). Tetrahedron, 61, 6108–6114. Web of Science CSD CrossRef CAS Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 2| February 2009| Page o372

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