organic compounds
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
The title compound, C18H28N4O6, crystallizes with two molecules in the 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 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); Sykes et al. (1999).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536811049749/gk2433sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049749/gk2433Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811049749/gk2433Isup3.cml
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
(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.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
effect Friedel pairs were merged. The was determined relative to the known chiral centers.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).
Data collection: APEX2 (Bruker, 2007); cell
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).C18H28N4O6 | F(000) = 1696 |
Mr = 396.44 | Dx = 1.261 Mg m−3 |
Monoclinic, I2 | Melting point: 426 K |
Hall symbol: I 2y | Mo Kα radiation, λ = 0.71073 Å |
a = 21.1662 (16) Å | Cell parameters from 12448 reflections |
b = 9.8317 (7) Å | θ = 1.0–27.7° |
c = 22.565 (2) Å | µ = 0.10 mm−1 |
β = 117.163 (1)° | T = 296 K |
V = 4177.8 (6) Å3 | Block, colourless |
Z = 8 | 0.68 × 0.22 × 0.10 mm |
Bruker APEXII CCD area-detector diffractometer | 5062 independent reflections |
Radiation source: fine-focus sealed tube | 2956 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
phi and ω scans | θmax = 27.7°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −27→27 |
Tmin = 0.938, Tmax = 0.990 | k = −10→12 |
12447 measured reflections | l = −29→28 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-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 parameters | Δρmax = 0.62 e Å−3 |
9 restraints | Δρmin = −0.23 e Å−3 |
C18H28N4O6 | V = 4177.8 (6) Å3 |
Mr = 396.44 | Z = 8 |
Monoclinic, I2 | Mo Kα radiation |
a = 21.1662 (16) Å | µ = 0.10 mm−1 |
b = 9.8317 (7) Å | T = 296 K |
c = 22.565 (2) Å | 0.68 × 0.22 × 0.10 mm |
β = 117.163 (1)° |
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 = 0.990 | Rint = 0.031 |
12447 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 9 restraints |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.62 e Å−3 |
5062 reflections | Δρmin = −0.23 e Å−3 |
505 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2149 (3) | 0.0458 (5) | 0.4202 (2) | 0.0657 (13) | |
H1A | 0.2120 | 0.0726 | 0.4584 | 0.079* | |
C2 | 0.2775 (3) | 0.0626 (5) | 0.4176 (2) | 0.0601 (12) | |
C3 | 0.2829 (3) | 0.0145 (5) | 0.3604 (2) | 0.0536 (11) | |
C4 | 0.2239 (2) | −0.0351 (4) | 0.3071 (2) | 0.0496 (10) | |
C5 | 0.1559 (3) | −0.0464 (5) | 0.3066 (2) | 0.0559 (11) | |
C6 | 0.1564 (3) | −0.0089 (5) | 0.3689 (2) | 0.0606 (12) | |
C7 | 0.0754 (3) | −0.0949 (9) | 0.1834 (3) | 0.094 (2) | |
H7A | 0.1180 | −0.0939 | 0.1766 | 0.113* | |
C8 | 0.4036 (3) | −0.0608 (9) | 0.4051 (3) | 0.104 (2) | |
H8A | 0.4435 | −0.0541 | 0.3958 | 0.156* | |
H8B | 0.3907 | −0.1546 | 0.4044 | 0.156* | |
H8C | 0.4161 | −0.0231 | 0.4483 | 0.156* | |
C9 | 0.2352 (2) | −0.0956 (5) | 0.2504 (2) | 0.0508 (10) | |
C10 | 0.2536 (3) | −0.0434 (6) | 0.1525 (2) | 0.0695 (14) | |
H10A | 0.2298 | −0.1309 | 0.1358 | 0.083* | |
C11 | 0.2157 (6) | 0.0619 (14) | 0.0979 (4) | 0.176 (6) | |
H11A | 0.1670 | 0.0688 | 0.0891 | 0.264* | |
H11B | 0.2179 | 0.0345 | 0.0580 | 0.264* | |
H11C | 0.2385 | 0.1486 | 0.1122 | 0.264* | |
C12 | 0.3296 (4) | −0.0607 (8) | 0.1670 (4) | 0.095 (2) | |
H12A | 0.3301 | −0.0869 | 0.1253 | 0.114* | |
C13 | 0.3716 (5) | −0.1605 (11) | 0.2172 (4) | 0.129 (3) | |
H13A | 0.3493 | −0.2481 | 0.2047 | 0.193* | |
H13B | 0.3747 | −0.1344 | 0.2594 | 0.193* | |
H13C | 0.4184 | −0.1650 | 0.2205 | 0.193* | |
C14 | 0.3696 (7) | 0.0804 (12) | 0.1895 (8) | 0.208 (7) | |
H14A | 0.4182 | 0.0694 | 0.1985 | 0.313* | |
H14B | 0.3678 | 0.1113 | 0.2291 | 0.313* | |
H14C | 0.3470 | 0.1461 | 0.1546 | 0.313* | |
C15 | 0.2353 (2) | 0.3234 (5) | 0.93893 (19) | 0.0521 (10) | |
H15A | 0.2345 | 0.3099 | 0.9794 | 0.063* | |
C16 | 0.2961 (2) | 0.3005 (4) | 0.93438 (19) | 0.0490 (10) | |
C17 | 0.2997 (2) | 0.3289 (4) | 0.87464 (18) | 0.0467 (9) | |
C18 | 0.23767 (19) | 0.3671 (4) | 0.81838 (17) | 0.0394 (8) | |
C19 | 0.17142 (19) | 0.3801 (4) | 0.82059 (17) | 0.0398 (8) | |
C20 | 0.1747 (2) | 0.3663 (5) | 0.8847 (2) | 0.0497 (10) | |
C21 | 0.24722 (19) | 0.4191 (4) | 0.76034 (19) | 0.0399 (9) | |
C22 | 0.4217 (3) | 0.3907 (7) | 0.9148 (3) | 0.0807 (16) | |
H22A | 0.4590 | 0.3786 | 0.9023 | 0.121* | |
H22B | 0.4357 | 0.3512 | 0.9579 | 0.121* | |
H22C | 0.4128 | 0.4860 | 0.9164 | 0.121* | |
C23 | 0.0912 (2) | 0.3596 (5) | 0.69793 (18) | 0.0498 (10) | |
H23A | 0.1288 | 0.3864 | 0.6864 | 0.060* | |
C24 | 0.2849 (2) | 0.3677 (5) | 0.6750 (2) | 0.0521 (10) | |
H24A | 0.3017 | 0.4620 | 0.6828 | 0.063* | |
C25 | 0.3471 (3) | 0.2764 (7) | 0.6830 (3) | 0.0794 (16) | |
H25A | 0.3855 | 0.2871 | 0.7270 | 0.119* | |
H25B | 0.3628 | 0.3018 | 0.6507 | 0.119* | |
H25C | 0.3320 | 0.1831 | 0.6762 | 0.119* | |
C26 | 0.2207 (3) | 0.3596 (6) | 0.6053 (2) | 0.0685 (14) | |
H26A | 0.1826 | 0.4139 | 0.6069 | 0.082* | |
C27 | 0.1923 (4) | 0.2182 (8) | 0.5859 (3) | 0.097 (2) | |
H27A | 0.1819 | 0.1803 | 0.6196 | 0.145* | |
H27B | 0.2272 | 0.1629 | 0.5812 | 0.145* | |
H27C | 0.1498 | 0.2208 | 0.5443 | 0.145* | |
C28 | 0.2375 (4) | 0.4239 (7) | 0.5523 (3) | 0.100 (2) | |
H28A | 0.1968 | 0.4163 | 0.5094 | 0.150* | |
H28B | 0.2770 | 0.3776 | 0.5515 | 0.150* | |
H28C | 0.2491 | 0.5182 | 0.5627 | 0.150* | |
N1 | 0.0926 (3) | −0.0156 (6) | 0.3776 (3) | 0.0814 (13) | |
N2 | 0.3328 (3) | 0.1353 (5) | 0.4711 (2) | 0.0753 (12) | |
N3 | 0.2437 (2) | −0.0073 (4) | 0.21059 (17) | 0.0564 (9) | |
H3A | 0.2435 | 0.0777 | 0.2195 | 0.068* | |
N4 | 0.3536 (2) | 0.2302 (5) | 0.99008 (18) | 0.0655 (11) | |
N5 | 0.1125 (2) | 0.3863 (5) | 0.89616 (19) | 0.0641 (11) | |
N6 | 0.26495 (17) | 0.3299 (3) | 0.72681 (15) | 0.0440 (7) | |
H6A | 0.2648 | 0.2450 | 0.7360 | 0.053* | |
O1 | 0.0952 (3) | 0.0318 (6) | 0.4284 (3) | 0.1188 (18) | |
O2 | 0.3313 (2) | 0.1448 (5) | 0.5239 (2) | 0.0986 (14) | |
O3 | 0.0388 (2) | −0.0701 (6) | 0.3351 (2) | 0.1003 (15) | |
O4 | 0.3773 (3) | 0.1932 (6) | 0.4594 (2) | 0.1203 (19) | |
N7 | 0.0976 (2) | −0.0935 (5) | 0.2554 (2) | 0.0702 (11) | |
H7B | 0.0675 | −0.1296 | 0.2664 | 0.084* | |
O6 | 0.34459 (17) | 0.0131 (4) | 0.35551 (15) | 0.0648 (9) | |
O7 | 0.2352 (2) | −0.2202 (3) | 0.24356 (19) | 0.0683 (9) | |
O8 | 0.3963 (2) | 0.1660 (5) | 0.9792 (2) | 0.1004 (14) | |
O9 | 0.3522 (2) | 0.2307 (5) | 1.04399 (16) | 0.0983 (14) | |
O10 | 0.1161 (2) | 0.3519 (5) | 0.94979 (17) | 0.0871 (12) | |
O11 | 0.05903 (19) | 0.4372 (5) | 0.85230 (18) | 0.0852 (13) | |
N8 | 0.11081 (17) | 0.4067 (4) | 0.76599 (15) | 0.0479 (8) | |
H8D | 0.0803 | 0.4564 | 0.7712 | 0.058* | |
O13 | 0.35904 (14) | 0.3261 (4) | 0.86735 (14) | 0.0668 (10) | |
O14 | 0.23905 (17) | 0.5416 (3) | 0.74670 (16) | 0.0528 (7) | |
C33 | 0.0220 (2) | 0.4323 (5) | 0.6502 (2) | 0.0568 (12) | |
H33A | −0.0146 | 0.4086 | 0.6635 | 0.068* | |
C34 | 0.0310 (3) | 0.5837 (7) | 0.6548 (4) | 0.108 (2) | |
H34A | 0.0465 | 0.6121 | 0.7000 | 0.162* | |
H34B | −0.0135 | 0.6264 | 0.6266 | 0.162* | |
H34C | 0.0658 | 0.6097 | 0.6407 | 0.162* | |
C35 | −0.0028 (3) | 0.3829 (10) | 0.5789 (2) | 0.108 (2) | |
H35A | −0.0462 | 0.4281 | 0.5499 | 0.162* | |
H35B | −0.0107 | 0.2865 | 0.5768 | 0.162* | |
H35C | 0.0329 | 0.4030 | 0.5651 | 0.162* | |
C36 | 0.0854 (3) | 0.2077 (6) | 0.6950 (3) | 0.0895 (18) | |
H36A | 0.1302 | 0.1687 | 0.7254 | 0.134* | |
H36B | 0.0730 | 0.1774 | 0.6506 | 0.134* | |
H36C | 0.0495 | 0.1796 | 0.7072 | 0.134* | |
C29 | 0.0361 (5) | −0.2255 (10) | 0.1558 (4) | 0.142 (3) | |
H29A | 0.0674 | −0.3010 | 0.1761 | 0.212* | |
H29B | 0.0196 | −0.2278 | 0.1085 | 0.212* | |
H29C | −0.0036 | −0.2311 | 0.1653 | 0.212* | |
C30 | 0.0320 (7) | 0.0370 (14) | 0.1527 (5) | 0.167 (5) | |
H30A | 0.0607 | 0.1154 | 0.1769 | 0.200* | |
C31 | 0.0144 (10) | 0.051 (2) | 0.0775 (5) | 0.299 (11) | |
H31A | −0.0137 | 0.1308 | 0.0591 | 0.448* | |
H31B | −0.0118 | −0.0280 | 0.0535 | 0.448* | |
H31C | 0.0577 | 0.0572 | 0.0739 | 0.448* | |
C32 | −0.0292 (8) | 0.041 (2) | 0.1559 (7) | 0.230 (7) | |
H32A | −0.0200 | 0.0389 | 0.2017 | 0.344* | |
H32B | −0.0577 | −0.0362 | 0.1330 | 0.344* | |
H32C | −0.0542 | 0.1231 | 0.1354 | 0.344* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.090 (4) | 0.063 (3) | 0.058 (3) | 0.023 (3) | 0.046 (3) | 0.012 (2) |
C2 | 0.074 (3) | 0.054 (3) | 0.053 (3) | 0.007 (2) | 0.029 (2) | 0.006 (2) |
C3 | 0.069 (3) | 0.047 (2) | 0.058 (3) | 0.005 (2) | 0.040 (2) | 0.006 (2) |
C4 | 0.061 (3) | 0.043 (2) | 0.052 (2) | 0.0032 (19) | 0.031 (2) | 0.0044 (19) |
C5 | 0.070 (3) | 0.045 (2) | 0.065 (3) | 0.007 (2) | 0.041 (3) | 0.005 (2) |
C6 | 0.073 (3) | 0.060 (3) | 0.065 (3) | 0.011 (2) | 0.046 (3) | 0.008 (2) |
C7 | 0.061 (3) | 0.138 (6) | 0.079 (4) | −0.009 (4) | 0.028 (3) | −0.031 (4) |
C8 | 0.082 (4) | 0.133 (7) | 0.099 (4) | 0.036 (4) | 0.044 (4) | 0.033 (4) |
C9 | 0.059 (3) | 0.045 (3) | 0.056 (2) | 0.000 (2) | 0.033 (2) | 0.001 (2) |
C10 | 0.085 (4) | 0.074 (4) | 0.056 (3) | 0.000 (3) | 0.038 (3) | 0.001 (3) |
C11 | 0.233 (11) | 0.234 (14) | 0.103 (6) | 0.110 (11) | 0.114 (7) | 0.078 (8) |
C12 | 0.106 (5) | 0.102 (5) | 0.100 (4) | 0.006 (4) | 0.067 (4) | −0.019 (4) |
C13 | 0.139 (7) | 0.127 (7) | 0.150 (7) | −0.004 (6) | 0.091 (6) | 0.000 (6) |
C14 | 0.228 (12) | 0.121 (8) | 0.39 (2) | −0.074 (8) | 0.240 (14) | −0.105 (11) |
C15 | 0.064 (3) | 0.054 (3) | 0.0350 (19) | −0.007 (2) | 0.0199 (19) | −0.0027 (19) |
C16 | 0.054 (2) | 0.045 (2) | 0.0362 (19) | 0.0025 (18) | 0.0102 (18) | 0.0007 (18) |
C17 | 0.050 (2) | 0.044 (2) | 0.042 (2) | 0.0044 (18) | 0.0171 (19) | −0.0043 (18) |
C18 | 0.0428 (19) | 0.036 (2) | 0.0350 (17) | 0.0004 (16) | 0.0135 (16) | −0.0025 (16) |
C19 | 0.042 (2) | 0.039 (2) | 0.0390 (19) | −0.0017 (16) | 0.0183 (17) | −0.0023 (16) |
C20 | 0.052 (2) | 0.053 (3) | 0.049 (2) | −0.003 (2) | 0.028 (2) | −0.002 (2) |
C21 | 0.0393 (19) | 0.035 (2) | 0.043 (2) | −0.0028 (16) | 0.0161 (16) | −0.0018 (17) |
C22 | 0.060 (3) | 0.079 (4) | 0.096 (4) | −0.003 (3) | 0.029 (3) | 0.002 (3) |
C23 | 0.044 (2) | 0.063 (3) | 0.0373 (19) | 0.001 (2) | 0.0141 (17) | 0.003 (2) |
C24 | 0.065 (3) | 0.048 (2) | 0.056 (2) | 0.001 (2) | 0.039 (2) | 0.004 (2) |
C25 | 0.071 (3) | 0.100 (4) | 0.081 (3) | 0.018 (3) | 0.047 (3) | 0.015 (3) |
C26 | 0.080 (3) | 0.077 (4) | 0.056 (3) | 0.023 (3) | 0.037 (2) | 0.016 (3) |
C27 | 0.113 (5) | 0.106 (5) | 0.063 (3) | −0.019 (4) | 0.034 (3) | −0.015 (4) |
C28 | 0.145 (6) | 0.095 (5) | 0.086 (4) | 0.044 (4) | 0.074 (4) | 0.036 (4) |
N1 | 0.085 (3) | 0.089 (3) | 0.098 (4) | 0.015 (3) | 0.066 (3) | 0.013 (3) |
N2 | 0.087 (3) | 0.075 (3) | 0.060 (3) | 0.006 (3) | 0.030 (2) | −0.005 (2) |
N3 | 0.076 (3) | 0.047 (2) | 0.054 (2) | 0.0021 (18) | 0.036 (2) | −0.0006 (18) |
N4 | 0.071 (3) | 0.066 (3) | 0.044 (2) | −0.002 (2) | 0.0124 (19) | 0.008 (2) |
N5 | 0.063 (2) | 0.083 (3) | 0.057 (2) | −0.013 (2) | 0.036 (2) | −0.014 (2) |
N6 | 0.0568 (19) | 0.0363 (17) | 0.0436 (16) | 0.0000 (15) | 0.0270 (15) | 0.0033 (15) |
O1 | 0.127 (4) | 0.154 (5) | 0.125 (4) | 0.016 (4) | 0.101 (3) | −0.010 (4) |
O2 | 0.119 (3) | 0.115 (4) | 0.064 (2) | 0.008 (3) | 0.044 (2) | −0.024 (2) |
O3 | 0.075 (3) | 0.140 (4) | 0.106 (3) | 0.001 (3) | 0.058 (3) | 0.005 (3) |
O4 | 0.126 (4) | 0.139 (5) | 0.093 (3) | −0.054 (4) | 0.047 (3) | −0.039 (3) |
N7 | 0.062 (2) | 0.081 (3) | 0.076 (3) | −0.008 (2) | 0.039 (2) | −0.008 (2) |
O6 | 0.0598 (19) | 0.080 (2) | 0.0599 (18) | −0.0005 (16) | 0.0322 (16) | 0.0067 (17) |
O7 | 0.091 (3) | 0.0421 (18) | 0.084 (2) | 0.0023 (16) | 0.050 (2) | −0.0027 (17) |
O8 | 0.089 (3) | 0.115 (4) | 0.091 (3) | 0.049 (3) | 0.036 (2) | 0.045 (3) |
O9 | 0.115 (3) | 0.113 (4) | 0.0389 (18) | 0.021 (3) | 0.0106 (19) | 0.014 (2) |
O10 | 0.096 (3) | 0.122 (3) | 0.066 (2) | −0.016 (3) | 0.0562 (19) | −0.003 (2) |
O11 | 0.059 (2) | 0.135 (4) | 0.071 (2) | 0.018 (2) | 0.038 (2) | −0.002 (2) |
N8 | 0.0408 (17) | 0.058 (2) | 0.0414 (17) | 0.0061 (16) | 0.0153 (14) | −0.0012 (17) |
O13 | 0.0403 (16) | 0.103 (3) | 0.0490 (15) | 0.0133 (17) | 0.0134 (13) | −0.0031 (18) |
O14 | 0.075 (2) | 0.0330 (16) | 0.0576 (16) | −0.0021 (14) | 0.0363 (15) | −0.0008 (13) |
C33 | 0.040 (2) | 0.078 (3) | 0.044 (2) | −0.001 (2) | 0.0121 (18) | 0.011 (2) |
C34 | 0.086 (4) | 0.080 (4) | 0.106 (5) | 0.011 (3) | −0.002 (4) | 0.026 (4) |
C35 | 0.080 (4) | 0.164 (8) | 0.051 (3) | 0.021 (5) | 0.004 (3) | 0.006 (4) |
C36 | 0.095 (4) | 0.068 (4) | 0.073 (4) | 0.007 (3) | 0.010 (3) | −0.011 (3) |
C29 | 0.145 (7) | 0.101 (6) | 0.128 (7) | 0.002 (5) | 0.017 (6) | −0.042 (5) |
C30 | 0.191 (11) | 0.158 (10) | 0.096 (6) | −0.038 (9) | 0.017 (7) | 0.036 (6) |
C31 | 0.41 (2) | 0.30 (3) | 0.098 (7) | −0.07 (2) | 0.037 (11) | 0.009 (11) |
C32 | 0.253 (10) | 0.196 (10) | 0.224 (10) | 0.044 (9) | 0.095 (8) | 0.049 (8) |
C1—C6 | 1.361 (7) | C23—N8 | 1.471 (5) |
C1—C2 | 1.364 (7) | C23—C36 | 1.497 (7) |
C1—H1A | 0.9300 | C23—C33 | 1.541 (6) |
C2—C3 | 1.428 (6) | C23—H23A | 0.9800 |
C2—N2 | 1.430 (7) | C24—N6 | 1.461 (5) |
C3—O6 | 1.359 (5) | C24—C25 | 1.536 (7) |
C3—C4 | 1.368 (6) | C24—C26 | 1.541 (7) |
C4—C5 | 1.440 (6) | C24—H24A | 0.9800 |
C4—C9 | 1.525 (6) | C25—H25A | 0.9600 |
C5—N7 | 1.330 (6) | C25—H25B | 0.9600 |
C5—C6 | 1.447 (6) | C25—H25C | 0.9600 |
C6—N1 | 1.453 (6) | C26—C27 | 1.498 (9) |
C7—N7 | 1.472 (7) | C26—C28 | 1.533 (7) |
C7—C29 | 1.501 (12) | C26—H26A | 0.9800 |
C7—C30 | 1.557 (15) | C27—H27A | 0.9600 |
C7—H7A | 0.9800 | C27—H27B | 0.9600 |
C8—O6 | 1.437 (7) | C27—H27C | 0.9600 |
C8—H8A | 0.9600 | C28—H28A | 0.9600 |
C8—H8B | 0.9600 | C28—H28B | 0.9600 |
C8—H8C | 0.9600 | C28—H28C | 0.9600 |
C9—O7 | 1.236 (6) | N1—O1 | 1.215 (6) |
C9—N3 | 1.320 (6) | N1—O3 | 1.228 (7) |
C10—N3 | 1.463 (6) | N2—O2 | 1.212 (5) |
C10—C12 | 1.498 (8) | N2—O4 | 1.226 (6) |
C10—C11 | 1.526 (10) | N3—H3A | 0.8600 |
C10—H10A | 0.9800 | N4—O8 | 1.215 (6) |
C11—H11A | 0.9600 | N4—O9 | 1.231 (5) |
C11—H11B | 0.9600 | N5—O11 | 1.219 (5) |
C11—H11C | 0.9600 | N5—O10 | 1.225 (5) |
C12—C13 | 1.454 (11) | N6—H6A | 0.8600 |
C12—C14 | 1.583 (12) | N7—H7B | 0.8600 |
C12—H12A | 0.9800 | N8—H8D | 0.8600 |
C13—H13A | 0.9600 | C33—C34 | 1.499 (9) |
C13—H13B | 0.9600 | C33—C35 | 1.526 (7) |
C13—H13C | 0.9600 | C33—H33A | 0.9800 |
C14—H14A | 0.9600 | C34—H34A | 0.9600 |
C14—H14B | 0.9600 | C34—H34B | 0.9600 |
C14—H14C | 0.9600 | C34—H34C | 0.9600 |
C15—C16 | 1.357 (6) | C35—H35A | 0.9600 |
C15—C20 | 1.373 (6) | C35—H35B | 0.9600 |
C15—H15A | 0.9300 | C35—H35C | 0.9600 |
C16—C17 | 1.412 (5) | C36—H36A | 0.9600 |
C16—N4 | 1.463 (6) | C36—H36B | 0.9600 |
C17—O13 | 1.340 (5) | C36—H36C | 0.9600 |
C17—C18 | 1.398 (5) | C29—H29A | 0.9600 |
C18—C19 | 1.432 (5) | C29—H29B | 0.9600 |
C18—C21 | 1.503 (5) | C29—H29C | 0.9600 |
C19—N8 | 1.337 (5) | C30—C32 | 1.332 (16) |
C19—C20 | 1.422 (5) | C30—C31 | 1.567 (15) |
C20—N5 | 1.468 (5) | C30—H30A | 0.9800 |
C21—O14 | 1.236 (5) | C31—H31A | 0.9600 |
C21—N6 | 1.320 (5) | C31—H31B | 0.9600 |
C22—O13 | 1.419 (6) | C31—H31C | 0.9600 |
C22—H22A | 0.9600 | C32—H32A | 0.9600 |
C22—H22B | 0.9600 | C32—H32B | 0.9600 |
C22—H22C | 0.9600 | C32—H32C | 0.9600 |
C6—C1—C2 | 122.4 (4) | C25—C24—H24A | 108.1 |
C6—C1—H1A | 118.8 | C26—C24—H24A | 108.1 |
C2—C1—H1A | 118.8 | C24—C25—H25A | 109.5 |
C1—C2—C3 | 118.6 (5) | C24—C25—H25B | 109.5 |
C1—C2—N2 | 117.5 (4) | H25A—C25—H25B | 109.5 |
C3—C2—N2 | 123.8 (5) | C24—C25—H25C | 109.5 |
O6—C3—C4 | 116.8 (4) | H25A—C25—H25C | 109.5 |
O6—C3—C2 | 123.5 (4) | H25B—C25—H25C | 109.5 |
C4—C3—C2 | 119.6 (4) | C27—C26—C28 | 111.0 (5) |
C3—C4—C5 | 122.9 (4) | C27—C26—C24 | 113.3 (4) |
C3—C4—C9 | 116.5 (4) | C28—C26—C24 | 111.3 (5) |
C5—C4—C9 | 120.2 (4) | C27—C26—H26A | 106.9 |
N7—C5—C4 | 124.1 (4) | C28—C26—H26A | 106.9 |
N7—C5—C6 | 121.7 (4) | C24—C26—H26A | 106.9 |
C4—C5—C6 | 114.1 (4) | C26—C27—H27A | 109.5 |
C1—C6—C5 | 121.9 (4) | C26—C27—H27B | 109.5 |
C1—C6—N1 | 116.3 (4) | H27A—C27—H27B | 109.5 |
C5—C6—N1 | 121.6 (5) | C26—C27—H27C | 109.5 |
N7—C7—C29 | 107.6 (7) | H27A—C27—H27C | 109.5 |
N7—C7—C30 | 108.0 (7) | H27B—C27—H27C | 109.5 |
C29—C7—C30 | 115.2 (6) | C26—C28—H28A | 109.5 |
N7—C7—H7A | 108.6 | C26—C28—H28B | 109.5 |
C29—C7—H7A | 108.6 | H28A—C28—H28B | 109.5 |
C30—C7—H7A | 108.6 | C26—C28—H28C | 109.5 |
O6—C8—H8A | 109.5 | H28A—C28—H28C | 109.5 |
O6—C8—H8B | 109.5 | H28B—C28—H28C | 109.5 |
H8A—C8—H8B | 109.5 | O1—N1—O3 | 122.1 (5) |
O6—C8—H8C | 109.5 | O1—N1—C6 | 117.8 (6) |
H8A—C8—H8C | 109.5 | O3—N1—C6 | 120.1 (5) |
H8B—C8—H8C | 109.5 | O2—N2—O4 | 122.8 (5) |
O7—C9—N3 | 124.0 (4) | O2—N2—C2 | 119.3 (5) |
O7—C9—C4 | 120.1 (4) | O4—N2—C2 | 117.6 (4) |
N3—C9—C4 | 115.9 (4) | C9—N3—C10 | 124.8 (4) |
N3—C10—C12 | 114.2 (5) | C9—N3—H3A | 117.6 |
N3—C10—C11 | 108.7 (5) | C10—N3—H3A | 117.6 |
C12—C10—C11 | 111.7 (6) | O8—N4—O9 | 123.9 (4) |
N3—C10—H10A | 107.3 | O8—N4—C16 | 118.4 (4) |
C12—C10—H10A | 107.3 | O9—N4—C16 | 117.4 (4) |
C11—C10—H10A | 107.3 | O11—N5—O10 | 122.1 (4) |
C10—C11—H11A | 109.5 | O11—N5—C20 | 119.1 (4) |
C10—C11—H11B | 109.5 | O10—N5—C20 | 118.8 (4) |
H11A—C11—H11B | 109.5 | C21—N6—C24 | 123.5 (3) |
C10—C11—H11C | 109.5 | C21—N6—H6A | 118.3 |
H11A—C11—H11C | 109.5 | C24—N6—H6A | 118.3 |
H11B—C11—H11C | 109.5 | C5—N7—C7 | 131.7 (4) |
C13—C12—C10 | 117.4 (6) | C5—N7—H7B | 114.2 |
C13—C12—C14 | 107.2 (8) | C7—N7—H7B | 114.2 |
C10—C12—C14 | 109.5 (6) | C3—O6—C8 | 117.9 (4) |
C13—C12—H12A | 107.4 | C19—N8—C23 | 126.5 (3) |
C10—C12—H12A | 107.4 | C19—N8—H8D | 116.7 |
C14—C12—H12A | 107.4 | C23—N8—H8D | 116.7 |
C12—C13—H13A | 109.5 | C17—O13—C22 | 120.3 (4) |
C12—C13—H13B | 109.5 | C34—C33—C35 | 111.1 (6) |
H13A—C13—H13B | 109.5 | C34—C33—C23 | 111.3 (4) |
C12—C13—H13C | 109.5 | C35—C33—C23 | 110.5 (4) |
H13A—C13—H13C | 109.5 | C34—C33—H33A | 107.9 |
H13B—C13—H13C | 109.5 | C35—C33—H33A | 107.9 |
C12—C14—H14A | 109.5 | C23—C33—H33A | 107.9 |
C12—C14—H14B | 109.5 | C33—C34—H34A | 109.5 |
H14A—C14—H14B | 109.5 | C33—C34—H34B | 109.5 |
C12—C14—H14C | 109.5 | H34A—C34—H34B | 109.5 |
H14A—C14—H14C | 109.5 | C33—C34—H34C | 109.5 |
H14B—C14—H14C | 109.5 | H34A—C34—H34C | 109.5 |
C16—C15—C20 | 121.0 (4) | H34B—C34—H34C | 109.5 |
C16—C15—H15A | 119.5 | C33—C35—H35A | 109.5 |
C20—C15—H15A | 119.5 | C33—C35—H35B | 109.5 |
C15—C16—C17 | 120.4 (4) | H35A—C35—H35B | 109.5 |
C15—C16—N4 | 117.4 (4) | C33—C35—H35C | 109.5 |
C17—C16—N4 | 121.8 (4) | H35A—C35—H35C | 109.5 |
O13—C17—C18 | 116.0 (3) | H35B—C35—H35C | 109.5 |
O13—C17—C16 | 125.1 (3) | C23—C36—H36A | 109.5 |
C18—C17—C16 | 118.9 (4) | C23—C36—H36B | 109.5 |
C17—C18—C19 | 121.4 (3) | H36A—C36—H36B | 109.5 |
C17—C18—C21 | 116.0 (3) | C23—C36—H36C | 109.5 |
C19—C18—C21 | 121.6 (3) | H36A—C36—H36C | 109.5 |
N8—C19—C20 | 122.5 (3) | H36B—C36—H36C | 109.5 |
N8—C19—C18 | 121.9 (3) | C7—C29—H29A | 109.5 |
C20—C19—C18 | 115.6 (3) | C7—C29—H29B | 109.5 |
C15—C20—C19 | 121.9 (4) | H29A—C29—H29B | 109.5 |
C15—C20—N5 | 115.5 (4) | C7—C29—H29C | 109.5 |
C19—C20—N5 | 122.4 (4) | H29A—C29—H29C | 109.5 |
O14—C21—N6 | 123.3 (4) | H29B—C29—H29C | 109.5 |
O14—C21—C18 | 119.3 (3) | C32—C30—C7 | 113.0 (12) |
N6—C21—C18 | 117.4 (3) | C32—C30—C31 | 107.5 (13) |
O13—C22—H22A | 109.5 | C7—C30—C31 | 110.7 (13) |
O13—C22—H22B | 109.5 | C32—C30—H30A | 108.5 |
H22A—C22—H22B | 109.5 | C7—C30—H30A | 108.5 |
O13—C22—H22C | 109.5 | C31—C30—H30A | 108.5 |
H22A—C22—H22C | 109.5 | C30—C31—H31A | 109.5 |
H22B—C22—H22C | 109.5 | C30—C31—H31B | 109.5 |
N8—C23—C36 | 109.8 (4) | H31A—C31—H31B | 109.5 |
N8—C23—C33 | 108.0 (3) | C30—C31—H31C | 109.5 |
C36—C23—C33 | 113.6 (4) | H31A—C31—H31C | 109.5 |
N8—C23—H23A | 108.5 | H31B—C31—H31C | 109.5 |
C36—C23—H23A | 108.5 | C30—C32—H32A | 109.5 |
C33—C23—H23A | 108.5 | C30—C32—H32B | 109.5 |
N6—C24—C25 | 107.6 (4) | H32A—C32—H32B | 109.5 |
N6—C24—C26 | 111.2 (3) | C30—C32—H32C | 109.5 |
C25—C24—C26 | 113.6 (4) | H32A—C32—H32C | 109.5 |
N6—C24—H24A | 108.1 | H32B—C32—H32C | 109.5 |
D—H···A | D—H | H···A | D···A | 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+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C18H28N4O6 |
Mr | 396.44 |
Crystal system, space group | Monoclinic, I2 |
Temperature (K) | 296 |
a, b, c (Å) | 21.1662 (16), 9.8317 (7), 22.565 (2) |
β (°) | 117.163 (1) |
V (Å3) | 4177.8 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.68 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.938, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12447, 5062, 2956 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.654 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.188, 0.99 |
No. of reflections | 5062 |
No. of parameters | 505 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.62, −0.23 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | 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+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+3/2. |
Acknowledgements
The authors thank Henan University of Traditional Chinese Medicine for supporting this study.
References
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Neft, N. & Farley, T. M. (1971). J. Med. Chem. 14, 1169-1170. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).