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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-Meth­­oxy-N-[(S)-3-methyl­butan-2-yl]-6-{[(S)-3-methyl­butan-2-yl]amino}-3,5-di­nitro­benzamide

aCollege of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou, Henan 450008, People's Republic of China, and bSchool of Civil Engineering and Communication, North China University of Water Source and Electric Power, Zhengzhou 450011, People's Republic of China
*Correspondence e-mail: wxf568@163.com

(Received 13 November 2011; accepted 21 November 2011; online 30 November 2011)

The title compound, C18H28N4O6, crystallizes with two mol­ecules in the asymmetric unit which differ slightly in conformation. The dihedral angle between the amide plane and the benzene ring are 72.6 (2) and 66.8 (2)° in the two mol­ecules. A strong intra­molecular N—H⋯O hydrogen bond between the amino and nitro groups occurs in each mol­ecule. The crystal structure features two symmetry-independent polymeric chains along [010] generated by N—H⋯O hydrogen bonds between the amide groups.

Related literature

For aromatic mol­ecules with amide, nitro and alk­oxy groups and their use in medicinal chemistry, see: Neft & Farley (1971[Neft, N. & Farley, T. M. (1971). J. Med. Chem. 14, 1169-1170.]); Sykes et al. (1999[Sykes, B. M., Atwell, G. J., Hogg, A., Wilson, W. R., O'Connor, C. J. & Denny, W. A. (1999). J. Med. Chem. 42, 346-355.]).

[Scheme 1]

Experimental

Crystal data
  • C18H28N4O6

  • Mr = 396.44

  • Monoclinic, I 2

  • a = 21.1662 (16) Å

  • b = 9.8317 (7) Å

  • c = 22.565 (2) Å

  • β = 117.163 (1)°

  • V = 4177.8 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.68 × 0.22 × 0.10 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.938, Tmax = 0.990

  • 12447 measured reflections

  • 5062 independent reflections

  • 2956 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.188

  • S = 0.99

  • 5062 reflections

  • 505 parameters

  • 9 restraints

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯O7i 0.86 2.12 2.967 (4) 168
N6—H6A⋯O14ii 0.86 2.05 2.906 (4) 177
N7—H7B⋯O3 0.86 1.99 2.619 (6) 129
N8—H8D⋯O11 0.86 2.08 2.654 (5) 123
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; 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

Amide, nitro and alkoxy groups exist in many active compounds, and have been shown to affect biological activity of compounds in varying degrees (Neft & Farley, 1971; Sykes et al., 1999). We synthesised the title compound and plan to examine its function as potential drug or as a prodrug.

The dihedral angle between the amide plane and the benzene ring in the two molecules are 72.6 (2)° and 66.8 (2)°, respectively. The molecules are linked by intermolecular N—H···O hydrogen bonding, forming one-dimensional infinite zigzag chain in the [010] directions, in which the amide H atom acts as a donor and the carbonyl group act as acceptor (Fig.2).

Related literature top

For aromatic molecules with amide, nitro and alkoxy groups and their use in medicinal chemistry, see: Neft & Farley (1971); Sykes et al. (1999).

Experimental top

To a solution of (S)-3-methylbutan-2-amine (0.45 g, 5 mmol)) in dry dichloromethane (30 ml) and triethylamine (1 mL) was added 2,6-dimethoxy-3,5-dinitrobenzoyl chloride (0.58 g, 2 mmol) at 0°C. The mixture was stirred at room temperature for another 2 h. The residue was subjected to chromatography (petroleum ether/acetone, 5:1) to provide the product as a yellow solid (80.8 mg, 10.2%). The crystal of the title compound was grown from ethyl acetate.

Refinement top

The C- and N-bound H-atoms were included in calculated positions and treated as riding atoms with C-H = 0.93, 0.96 and 0.98Å for CH(aromatic), CH3 and CH(methine) H atoms, respectively and N-H =0.86Å, with Uiso(H)= k Ueq(C,N), where k = 1.5 for CH3 H atoms and k = 1.2 for all other H atoms. The highest residual peak in the final electron-density difference map is located close to a strongly vibrating alkyl substituent. Due to negligible anomalous dispersion effect Friedel pairs were merged. The absolute structure was determined relative to the known chiral centers.

Structure description top

Amide, nitro and alkoxy groups exist in many active compounds, and have been shown to affect biological activity of compounds in varying degrees (Neft & Farley, 1971; Sykes et al., 1999). We synthesised the title compound and plan to examine its function as potential drug or as a prodrug.

The dihedral angle between the amide plane and the benzene ring in the two molecules are 72.6 (2)° and 66.8 (2)°, respectively. The molecules are linked by intermolecular N—H···O hydrogen bonding, forming one-dimensional infinite zigzag chain in the [010] directions, in which the amide H atom acts as a donor and the carbonyl group act as acceptor (Fig.2).

For aromatic molecules with amide, nitro and alkoxy groups and their use in medicinal chemistry, see: Neft & Farley (1971); Sykes et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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
[Figure 1] Fig. 1. A view of the molecular strcuture of the title compound; the displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the hydrogen bonded infinite zigzag chain in the [010] direction. The hydrogen bonds are shown as dashed lines and C-bound H atoms have been omitted for clarity.
[Figure 3] Fig. 3. A view of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines; C-bound H atoms have been omitted for clarity.
2-Methoxy-N-[(S)-3-methylbutan-2-yl]- 6-{[(S)-3-methylbutan-2-yl]amino}-3,5-dinitrobenzamide top
Crystal data top
C18H28N4O6F(000) = 1696
Mr = 396.44Dx = 1.261 Mg m3
Monoclinic, I2Melting point: 426 K
Hall symbol: I 2yMo Kα radiation, λ = 0.71073 Å
a = 21.1662 (16) ÅCell parameters from 12448 reflections
b = 9.8317 (7) Åθ = 1.0–27.7°
c = 22.565 (2) ŵ = 0.10 mm1
β = 117.163 (1)°T = 296 K
V = 4177.8 (6) Å3Block, colourless
Z = 80.68 × 0.22 × 0.10 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5062 independent reflections
Radiation source: fine-focus sealed tube2956 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
phi and ω scansθmax = 27.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2727
Tmin = 0.938, Tmax = 0.990k = 1012
12447 measured reflectionsl = 2928
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.110P)2]
where P = (Fo2 + 2Fc2)/3
5062 reflections(Δ/σ)max = 0.003
505 parametersΔρmax = 0.62 e Å3
9 restraintsΔρmin = 0.23 e Å3
Crystal data top
C18H28N4O6V = 4177.8 (6) Å3
Mr = 396.44Z = 8
Monoclinic, I2Mo Kα radiation
a = 21.1662 (16) ŵ = 0.10 mm1
b = 9.8317 (7) ÅT = 296 K
c = 22.565 (2) Å0.68 × 0.22 × 0.10 mm
β = 117.163 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5062 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2956 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.990Rint = 0.031
12447 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0609 restraints
wR(F2) = 0.188H-atom parameters constrained
S = 0.99Δρmax = 0.62 e Å3
5062 reflectionsΔρmin = 0.23 e Å3
505 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
C10.2149 (3)0.0458 (5)0.4202 (2)0.0657 (13)
H1A0.21200.07260.45840.079*
C20.2775 (3)0.0626 (5)0.4176 (2)0.0601 (12)
C30.2829 (3)0.0145 (5)0.3604 (2)0.0536 (11)
C40.2239 (2)0.0351 (4)0.3071 (2)0.0496 (10)
C50.1559 (3)0.0464 (5)0.3066 (2)0.0559 (11)
C60.1564 (3)0.0089 (5)0.3689 (2)0.0606 (12)
C70.0754 (3)0.0949 (9)0.1834 (3)0.094 (2)
H7A0.11800.09390.17660.113*
C80.4036 (3)0.0608 (9)0.4051 (3)0.104 (2)
H8A0.44350.05410.39580.156*
H8B0.39070.15460.40440.156*
H8C0.41610.02310.44830.156*
C90.2352 (2)0.0956 (5)0.2504 (2)0.0508 (10)
C100.2536 (3)0.0434 (6)0.1525 (2)0.0695 (14)
H10A0.22980.13090.13580.083*
C110.2157 (6)0.0619 (14)0.0979 (4)0.176 (6)
H11A0.16700.06880.08910.264*
H11B0.21790.03450.05800.264*
H11C0.23850.14860.11220.264*
C120.3296 (4)0.0607 (8)0.1670 (4)0.095 (2)
H12A0.33010.08690.12530.114*
C130.3716 (5)0.1605 (11)0.2172 (4)0.129 (3)
H13A0.34930.24810.20470.193*
H13B0.37470.13440.25940.193*
H13C0.41840.16500.22050.193*
C140.3696 (7)0.0804 (12)0.1895 (8)0.208 (7)
H14A0.41820.06940.19850.313*
H14B0.36780.11130.22910.313*
H14C0.34700.14610.15460.313*
C150.2353 (2)0.3234 (5)0.93893 (19)0.0521 (10)
H15A0.23450.30990.97940.063*
C160.2961 (2)0.3005 (4)0.93438 (19)0.0490 (10)
C170.2997 (2)0.3289 (4)0.87464 (18)0.0467 (9)
C180.23767 (19)0.3671 (4)0.81838 (17)0.0394 (8)
C190.17142 (19)0.3801 (4)0.82059 (17)0.0398 (8)
C200.1747 (2)0.3663 (5)0.8847 (2)0.0497 (10)
C210.24722 (19)0.4191 (4)0.76034 (19)0.0399 (9)
C220.4217 (3)0.3907 (7)0.9148 (3)0.0807 (16)
H22A0.45900.37860.90230.121*
H22B0.43570.35120.95790.121*
H22C0.41280.48600.91640.121*
C230.0912 (2)0.3596 (5)0.69793 (18)0.0498 (10)
H23A0.12880.38640.68640.060*
C240.2849 (2)0.3677 (5)0.6750 (2)0.0521 (10)
H24A0.30170.46200.68280.063*
C250.3471 (3)0.2764 (7)0.6830 (3)0.0794 (16)
H25A0.38550.28710.72700.119*
H25B0.36280.30180.65070.119*
H25C0.33200.18310.67620.119*
C260.2207 (3)0.3596 (6)0.6053 (2)0.0685 (14)
H26A0.18260.41390.60690.082*
C270.1923 (4)0.2182 (8)0.5859 (3)0.097 (2)
H27A0.18190.18030.61960.145*
H27B0.22720.16290.58120.145*
H27C0.14980.22080.54430.145*
C280.2375 (4)0.4239 (7)0.5523 (3)0.100 (2)
H28A0.19680.41630.50940.150*
H28B0.27700.37760.55150.150*
H28C0.24910.51820.56270.150*
N10.0926 (3)0.0156 (6)0.3776 (3)0.0814 (13)
N20.3328 (3)0.1353 (5)0.4711 (2)0.0753 (12)
N30.2437 (2)0.0073 (4)0.21059 (17)0.0564 (9)
H3A0.24350.07770.21950.068*
N40.3536 (2)0.2302 (5)0.99008 (18)0.0655 (11)
N50.1125 (2)0.3863 (5)0.89616 (19)0.0641 (11)
N60.26495 (17)0.3299 (3)0.72681 (15)0.0440 (7)
H6A0.26480.24500.73600.053*
O10.0952 (3)0.0318 (6)0.4284 (3)0.1188 (18)
O20.3313 (2)0.1448 (5)0.5239 (2)0.0986 (14)
O30.0388 (2)0.0701 (6)0.3351 (2)0.1003 (15)
O40.3773 (3)0.1932 (6)0.4594 (2)0.1203 (19)
N70.0976 (2)0.0935 (5)0.2554 (2)0.0702 (11)
H7B0.06750.12960.26640.084*
O60.34459 (17)0.0131 (4)0.35551 (15)0.0648 (9)
O70.2352 (2)0.2202 (3)0.24356 (19)0.0683 (9)
O80.3963 (2)0.1660 (5)0.9792 (2)0.1004 (14)
O90.3522 (2)0.2307 (5)1.04399 (16)0.0983 (14)
O100.1161 (2)0.3519 (5)0.94979 (17)0.0871 (12)
O110.05903 (19)0.4372 (5)0.85230 (18)0.0852 (13)
N80.11081 (17)0.4067 (4)0.76599 (15)0.0479 (8)
H8D0.08030.45640.77120.058*
O130.35904 (14)0.3261 (4)0.86735 (14)0.0668 (10)
O140.23905 (17)0.5416 (3)0.74670 (16)0.0528 (7)
C330.0220 (2)0.4323 (5)0.6502 (2)0.0568 (12)
H33A0.01460.40860.66350.068*
C340.0310 (3)0.5837 (7)0.6548 (4)0.108 (2)
H34A0.04650.61210.70000.162*
H34B0.01350.62640.62660.162*
H34C0.06580.60970.64070.162*
C350.0028 (3)0.3829 (10)0.5789 (2)0.108 (2)
H35A0.04620.42810.54990.162*
H35B0.01070.28650.57680.162*
H35C0.03290.40300.56510.162*
C360.0854 (3)0.2077 (6)0.6950 (3)0.0895 (18)
H36A0.13020.16870.72540.134*
H36B0.07300.17740.65060.134*
H36C0.04950.17960.70720.134*
C290.0361 (5)0.2255 (10)0.1558 (4)0.142 (3)
H29A0.06740.30100.17610.212*
H29B0.01960.22780.10850.212*
H29C0.00360.23110.16530.212*
C300.0320 (7)0.0370 (14)0.1527 (5)0.167 (5)
H30A0.06070.11540.17690.200*
C310.0144 (10)0.051 (2)0.0775 (5)0.299 (11)
H31A0.01370.13080.05910.448*
H31B0.01180.02800.05350.448*
H31C0.05770.05720.07390.448*
C320.0292 (8)0.041 (2)0.1559 (7)0.230 (7)
H32A0.02000.03890.20170.344*
H32B0.05770.03620.13300.344*
H32C0.05420.12310.13540.344*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.090 (4)0.063 (3)0.058 (3)0.023 (3)0.046 (3)0.012 (2)
C20.074 (3)0.054 (3)0.053 (3)0.007 (2)0.029 (2)0.006 (2)
C30.069 (3)0.047 (2)0.058 (3)0.005 (2)0.040 (2)0.006 (2)
C40.061 (3)0.043 (2)0.052 (2)0.0032 (19)0.031 (2)0.0044 (19)
C50.070 (3)0.045 (2)0.065 (3)0.007 (2)0.041 (3)0.005 (2)
C60.073 (3)0.060 (3)0.065 (3)0.011 (2)0.046 (3)0.008 (2)
C70.061 (3)0.138 (6)0.079 (4)0.009 (4)0.028 (3)0.031 (4)
C80.082 (4)0.133 (7)0.099 (4)0.036 (4)0.044 (4)0.033 (4)
C90.059 (3)0.045 (3)0.056 (2)0.000 (2)0.033 (2)0.001 (2)
C100.085 (4)0.074 (4)0.056 (3)0.000 (3)0.038 (3)0.001 (3)
C110.233 (11)0.234 (14)0.103 (6)0.110 (11)0.114 (7)0.078 (8)
C120.106 (5)0.102 (5)0.100 (4)0.006 (4)0.067 (4)0.019 (4)
C130.139 (7)0.127 (7)0.150 (7)0.004 (6)0.091 (6)0.000 (6)
C140.228 (12)0.121 (8)0.39 (2)0.074 (8)0.240 (14)0.105 (11)
C150.064 (3)0.054 (3)0.0350 (19)0.007 (2)0.0199 (19)0.0027 (19)
C160.054 (2)0.045 (2)0.0362 (19)0.0025 (18)0.0102 (18)0.0007 (18)
C170.050 (2)0.044 (2)0.042 (2)0.0044 (18)0.0171 (19)0.0043 (18)
C180.0428 (19)0.036 (2)0.0350 (17)0.0004 (16)0.0135 (16)0.0025 (16)
C190.042 (2)0.039 (2)0.0390 (19)0.0017 (16)0.0183 (17)0.0023 (16)
C200.052 (2)0.053 (3)0.049 (2)0.003 (2)0.028 (2)0.002 (2)
C210.0393 (19)0.035 (2)0.043 (2)0.0028 (16)0.0161 (16)0.0018 (17)
C220.060 (3)0.079 (4)0.096 (4)0.003 (3)0.029 (3)0.002 (3)
C230.044 (2)0.063 (3)0.0373 (19)0.001 (2)0.0141 (17)0.003 (2)
C240.065 (3)0.048 (2)0.056 (2)0.001 (2)0.039 (2)0.004 (2)
C250.071 (3)0.100 (4)0.081 (3)0.018 (3)0.047 (3)0.015 (3)
C260.080 (3)0.077 (4)0.056 (3)0.023 (3)0.037 (2)0.016 (3)
C270.113 (5)0.106 (5)0.063 (3)0.019 (4)0.034 (3)0.015 (4)
C280.145 (6)0.095 (5)0.086 (4)0.044 (4)0.074 (4)0.036 (4)
N10.085 (3)0.089 (3)0.098 (4)0.015 (3)0.066 (3)0.013 (3)
N20.087 (3)0.075 (3)0.060 (3)0.006 (3)0.030 (2)0.005 (2)
N30.076 (3)0.047 (2)0.054 (2)0.0021 (18)0.036 (2)0.0006 (18)
N40.071 (3)0.066 (3)0.044 (2)0.002 (2)0.0124 (19)0.008 (2)
N50.063 (2)0.083 (3)0.057 (2)0.013 (2)0.036 (2)0.014 (2)
N60.0568 (19)0.0363 (17)0.0436 (16)0.0000 (15)0.0270 (15)0.0033 (15)
O10.127 (4)0.154 (5)0.125 (4)0.016 (4)0.101 (3)0.010 (4)
O20.119 (3)0.115 (4)0.064 (2)0.008 (3)0.044 (2)0.024 (2)
O30.075 (3)0.140 (4)0.106 (3)0.001 (3)0.058 (3)0.005 (3)
O40.126 (4)0.139 (5)0.093 (3)0.054 (4)0.047 (3)0.039 (3)
N70.062 (2)0.081 (3)0.076 (3)0.008 (2)0.039 (2)0.008 (2)
O60.0598 (19)0.080 (2)0.0599 (18)0.0005 (16)0.0322 (16)0.0067 (17)
O70.091 (3)0.0421 (18)0.084 (2)0.0023 (16)0.050 (2)0.0027 (17)
O80.089 (3)0.115 (4)0.091 (3)0.049 (3)0.036 (2)0.045 (3)
O90.115 (3)0.113 (4)0.0389 (18)0.021 (3)0.0106 (19)0.014 (2)
O100.096 (3)0.122 (3)0.066 (2)0.016 (3)0.0562 (19)0.003 (2)
O110.059 (2)0.135 (4)0.071 (2)0.018 (2)0.038 (2)0.002 (2)
N80.0408 (17)0.058 (2)0.0414 (17)0.0061 (16)0.0153 (14)0.0012 (17)
O130.0403 (16)0.103 (3)0.0490 (15)0.0133 (17)0.0134 (13)0.0031 (18)
O140.075 (2)0.0330 (16)0.0576 (16)0.0021 (14)0.0363 (15)0.0008 (13)
C330.040 (2)0.078 (3)0.044 (2)0.001 (2)0.0121 (18)0.011 (2)
C340.086 (4)0.080 (4)0.106 (5)0.011 (3)0.002 (4)0.026 (4)
C350.080 (4)0.164 (8)0.051 (3)0.021 (5)0.004 (3)0.006 (4)
C360.095 (4)0.068 (4)0.073 (4)0.007 (3)0.010 (3)0.011 (3)
C290.145 (7)0.101 (6)0.128 (7)0.002 (5)0.017 (6)0.042 (5)
C300.191 (11)0.158 (10)0.096 (6)0.038 (9)0.017 (7)0.036 (6)
C310.41 (2)0.30 (3)0.098 (7)0.07 (2)0.037 (11)0.009 (11)
C320.253 (10)0.196 (10)0.224 (10)0.044 (9)0.095 (8)0.049 (8)
Geometric parameters (Å, º) top
C1—C61.361 (7)C23—N81.471 (5)
C1—C21.364 (7)C23—C361.497 (7)
C1—H1A0.9300C23—C331.541 (6)
C2—C31.428 (6)C23—H23A0.9800
C2—N21.430 (7)C24—N61.461 (5)
C3—O61.359 (5)C24—C251.536 (7)
C3—C41.368 (6)C24—C261.541 (7)
C4—C51.440 (6)C24—H24A0.9800
C4—C91.525 (6)C25—H25A0.9600
C5—N71.330 (6)C25—H25B0.9600
C5—C61.447 (6)C25—H25C0.9600
C6—N11.453 (6)C26—C271.498 (9)
C7—N71.472 (7)C26—C281.533 (7)
C7—C291.501 (12)C26—H26A0.9800
C7—C301.557 (15)C27—H27A0.9600
C7—H7A0.9800C27—H27B0.9600
C8—O61.437 (7)C27—H27C0.9600
C8—H8A0.9600C28—H28A0.9600
C8—H8B0.9600C28—H28B0.9600
C8—H8C0.9600C28—H28C0.9600
C9—O71.236 (6)N1—O11.215 (6)
C9—N31.320 (6)N1—O31.228 (7)
C10—N31.463 (6)N2—O21.212 (5)
C10—C121.498 (8)N2—O41.226 (6)
C10—C111.526 (10)N3—H3A0.8600
C10—H10A0.9800N4—O81.215 (6)
C11—H11A0.9600N4—O91.231 (5)
C11—H11B0.9600N5—O111.219 (5)
C11—H11C0.9600N5—O101.225 (5)
C12—C131.454 (11)N6—H6A0.8600
C12—C141.583 (12)N7—H7B0.8600
C12—H12A0.9800N8—H8D0.8600
C13—H13A0.9600C33—C341.499 (9)
C13—H13B0.9600C33—C351.526 (7)
C13—H13C0.9600C33—H33A0.9800
C14—H14A0.9600C34—H34A0.9600
C14—H14B0.9600C34—H34B0.9600
C14—H14C0.9600C34—H34C0.9600
C15—C161.357 (6)C35—H35A0.9600
C15—C201.373 (6)C35—H35B0.9600
C15—H15A0.9300C35—H35C0.9600
C16—C171.412 (5)C36—H36A0.9600
C16—N41.463 (6)C36—H36B0.9600
C17—O131.340 (5)C36—H36C0.9600
C17—C181.398 (5)C29—H29A0.9600
C18—C191.432 (5)C29—H29B0.9600
C18—C211.503 (5)C29—H29C0.9600
C19—N81.337 (5)C30—C321.332 (16)
C19—C201.422 (5)C30—C311.567 (15)
C20—N51.468 (5)C30—H30A0.9800
C21—O141.236 (5)C31—H31A0.9600
C21—N61.320 (5)C31—H31B0.9600
C22—O131.419 (6)C31—H31C0.9600
C22—H22A0.9600C32—H32A0.9600
C22—H22B0.9600C32—H32B0.9600
C22—H22C0.9600C32—H32C0.9600
C6—C1—C2122.4 (4)C25—C24—H24A108.1
C6—C1—H1A118.8C26—C24—H24A108.1
C2—C1—H1A118.8C24—C25—H25A109.5
C1—C2—C3118.6 (5)C24—C25—H25B109.5
C1—C2—N2117.5 (4)H25A—C25—H25B109.5
C3—C2—N2123.8 (5)C24—C25—H25C109.5
O6—C3—C4116.8 (4)H25A—C25—H25C109.5
O6—C3—C2123.5 (4)H25B—C25—H25C109.5
C4—C3—C2119.6 (4)C27—C26—C28111.0 (5)
C3—C4—C5122.9 (4)C27—C26—C24113.3 (4)
C3—C4—C9116.5 (4)C28—C26—C24111.3 (5)
C5—C4—C9120.2 (4)C27—C26—H26A106.9
N7—C5—C4124.1 (4)C28—C26—H26A106.9
N7—C5—C6121.7 (4)C24—C26—H26A106.9
C4—C5—C6114.1 (4)C26—C27—H27A109.5
C1—C6—C5121.9 (4)C26—C27—H27B109.5
C1—C6—N1116.3 (4)H27A—C27—H27B109.5
C5—C6—N1121.6 (5)C26—C27—H27C109.5
N7—C7—C29107.6 (7)H27A—C27—H27C109.5
N7—C7—C30108.0 (7)H27B—C27—H27C109.5
C29—C7—C30115.2 (6)C26—C28—H28A109.5
N7—C7—H7A108.6C26—C28—H28B109.5
C29—C7—H7A108.6H28A—C28—H28B109.5
C30—C7—H7A108.6C26—C28—H28C109.5
O6—C8—H8A109.5H28A—C28—H28C109.5
O6—C8—H8B109.5H28B—C28—H28C109.5
H8A—C8—H8B109.5O1—N1—O3122.1 (5)
O6—C8—H8C109.5O1—N1—C6117.8 (6)
H8A—C8—H8C109.5O3—N1—C6120.1 (5)
H8B—C8—H8C109.5O2—N2—O4122.8 (5)
O7—C9—N3124.0 (4)O2—N2—C2119.3 (5)
O7—C9—C4120.1 (4)O4—N2—C2117.6 (4)
N3—C9—C4115.9 (4)C9—N3—C10124.8 (4)
N3—C10—C12114.2 (5)C9—N3—H3A117.6
N3—C10—C11108.7 (5)C10—N3—H3A117.6
C12—C10—C11111.7 (6)O8—N4—O9123.9 (4)
N3—C10—H10A107.3O8—N4—C16118.4 (4)
C12—C10—H10A107.3O9—N4—C16117.4 (4)
C11—C10—H10A107.3O11—N5—O10122.1 (4)
C10—C11—H11A109.5O11—N5—C20119.1 (4)
C10—C11—H11B109.5O10—N5—C20118.8 (4)
H11A—C11—H11B109.5C21—N6—C24123.5 (3)
C10—C11—H11C109.5C21—N6—H6A118.3
H11A—C11—H11C109.5C24—N6—H6A118.3
H11B—C11—H11C109.5C5—N7—C7131.7 (4)
C13—C12—C10117.4 (6)C5—N7—H7B114.2
C13—C12—C14107.2 (8)C7—N7—H7B114.2
C10—C12—C14109.5 (6)C3—O6—C8117.9 (4)
C13—C12—H12A107.4C19—N8—C23126.5 (3)
C10—C12—H12A107.4C19—N8—H8D116.7
C14—C12—H12A107.4C23—N8—H8D116.7
C12—C13—H13A109.5C17—O13—C22120.3 (4)
C12—C13—H13B109.5C34—C33—C35111.1 (6)
H13A—C13—H13B109.5C34—C33—C23111.3 (4)
C12—C13—H13C109.5C35—C33—C23110.5 (4)
H13A—C13—H13C109.5C34—C33—H33A107.9
H13B—C13—H13C109.5C35—C33—H33A107.9
C12—C14—H14A109.5C23—C33—H33A107.9
C12—C14—H14B109.5C33—C34—H34A109.5
H14A—C14—H14B109.5C33—C34—H34B109.5
C12—C14—H14C109.5H34A—C34—H34B109.5
H14A—C14—H14C109.5C33—C34—H34C109.5
H14B—C14—H14C109.5H34A—C34—H34C109.5
C16—C15—C20121.0 (4)H34B—C34—H34C109.5
C16—C15—H15A119.5C33—C35—H35A109.5
C20—C15—H15A119.5C33—C35—H35B109.5
C15—C16—C17120.4 (4)H35A—C35—H35B109.5
C15—C16—N4117.4 (4)C33—C35—H35C109.5
C17—C16—N4121.8 (4)H35A—C35—H35C109.5
O13—C17—C18116.0 (3)H35B—C35—H35C109.5
O13—C17—C16125.1 (3)C23—C36—H36A109.5
C18—C17—C16118.9 (4)C23—C36—H36B109.5
C17—C18—C19121.4 (3)H36A—C36—H36B109.5
C17—C18—C21116.0 (3)C23—C36—H36C109.5
C19—C18—C21121.6 (3)H36A—C36—H36C109.5
N8—C19—C20122.5 (3)H36B—C36—H36C109.5
N8—C19—C18121.9 (3)C7—C29—H29A109.5
C20—C19—C18115.6 (3)C7—C29—H29B109.5
C15—C20—C19121.9 (4)H29A—C29—H29B109.5
C15—C20—N5115.5 (4)C7—C29—H29C109.5
C19—C20—N5122.4 (4)H29A—C29—H29C109.5
O14—C21—N6123.3 (4)H29B—C29—H29C109.5
O14—C21—C18119.3 (3)C32—C30—C7113.0 (12)
N6—C21—C18117.4 (3)C32—C30—C31107.5 (13)
O13—C22—H22A109.5C7—C30—C31110.7 (13)
O13—C22—H22B109.5C32—C30—H30A108.5
H22A—C22—H22B109.5C7—C30—H30A108.5
O13—C22—H22C109.5C31—C30—H30A108.5
H22A—C22—H22C109.5C30—C31—H31A109.5
H22B—C22—H22C109.5C30—C31—H31B109.5
N8—C23—C36109.8 (4)H31A—C31—H31B109.5
N8—C23—C33108.0 (3)C30—C31—H31C109.5
C36—C23—C33113.6 (4)H31A—C31—H31C109.5
N8—C23—H23A108.5H31B—C31—H31C109.5
C36—C23—H23A108.5C30—C32—H32A109.5
C33—C23—H23A108.5C30—C32—H32B109.5
N6—C24—C25107.6 (4)H32A—C32—H32B109.5
N6—C24—C26111.2 (3)C30—C32—H32C109.5
C25—C24—C26113.6 (4)H32A—C32—H32C109.5
N6—C24—H24A108.1H32B—C32—H32C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O7i0.862.122.967 (4)168
N6—H6A···O14ii0.862.052.906 (4)177
N7—H7B···O30.861.992.619 (6)129
N8—H8D···O110.862.082.654 (5)123
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC18H28N4O6
Mr396.44
Crystal system, space groupMonoclinic, I2
Temperature (K)296
a, b, c (Å)21.1662 (16), 9.8317 (7), 22.565 (2)
β (°) 117.163 (1)
V3)4177.8 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.68 × 0.22 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.938, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
12447, 5062, 2956
Rint0.031
(sin θ/λ)max1)0.654
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.188, 0.99
No. of reflections5062
No. of parameters505
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.62, 0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O7i0.862.122.967 (4)168
N6—H6A···O14ii0.862.052.906 (4)177
N7—H7B···O30.861.992.619 (6)129
N8—H8D···O110.862.082.654 (5)123
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+3/2.
 

Acknowledgements

The authors thank Henan University of Traditional Chinese Medicine for supporting this study.

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNeft, N. & Farley, T. M. (1971). J. Med. Chem. 14, 1169-1170.  CrossRef CAS PubMed Web of Science 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 citationSykes, B. M., Atwell, G. J., Hogg, A., Wilson, W. R., O'Connor, C. J. & Denny, W. A. (1999). J. Med. Chem. 42, 346–355.  Web of Science CrossRef CAS PubMed Google Scholar

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