organic compounds
N-(4-Methylphenyl)-N-{[(2-nitrophenyl)acetyl]oxy}benzamide
aGansu Health Center Hospital, Lanzhou 730000, Gansu Province, People's Republic of China, and bInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China
*Correspondence e-mail: qudonghui1020@126.com
In the title molecule, C22H18N2O5, the nitro-substituted benzene ring makes dihedral angles of 71.56 (1)° with the benzoyl ring and 16.28 (1)° with the methyl-substituted benzene ring. The features C—H⋯O interactions, which generate chains.
Related literature
For biological applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the preparation of the title compound, see: Ayyangark et al. (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812039360/zq2182sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039360/zq2182Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039360/zq2182Isup3.cml
The title compound was prepared according to the method described by Ayyangark et al. (1986). The yellow crystals were grown from a solution of dichloromethane–methanol (1:3 v/v) by slow evaporation at room temperature.
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å and Uiso = 1.2Ueq(C) for aromatic H atoms, with C—H = 0.97 Å and Uiso = 1.2Ueq(C) for methylene H atoms, and with C—H = 0.96 Å and Uiso = 1.5Ueq(C) for methyl H atoms.
Hydroxamic acid derivatives have received considerable attention in recent years as the result of the discovery of their role in the biochemical toxicology of many drugs and other chemicals. Thus, these compounds continue to attract much attention as potential biological agents (Noh et al., 2009; Zeng et al., 2003).
The title compound, C22H18N2O5, was prepared according to the method described by Ayyangark et al. (1986). The molecule contains three branched chains with its centre placed at midpoint of the N2 atom (Fig. 1). The nitro-substituted benzene ring makes a dihedral angle of 71.56 (1)° with the benzoyl ring and 16.28 (1)° with the methyl-substituted benzene ring. The
features weak intra- and inter-molecular C—H···O interactions (Table 1).For biological applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the preparation of the title compound, see: Ayyangark et al. (1986).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids (H atoms are shown as small spheres of arbitrary radius). |
C22H18N2O5 | F(000) = 816 |
Mr = 390.38 | Dx = 1.314 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2167 reflections |
a = 9.246 (3) Å | θ = 2.5–20.3° |
b = 11.911 (4) Å | µ = 0.09 mm−1 |
c = 17.923 (6) Å | T = 296 K |
V = 1974.0 (11) Å3 | Block, yellow |
Z = 4 | 0.25 × 0.23 × 0.22 mm |
Bruker APEXII CCD diffractometer | 3605 independent reflections |
Radiation source: fine-focus sealed tube | 2280 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.977, Tmax = 0.980 | k = −14→14 |
8939 measured reflections | l = −18→21 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.0436P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.040 | (Δ/σ)max = 0.001 |
wR(F2) = 0.111 | Δρmax = 0.11 e Å−3 |
S = 1.01 | Δρmin = −0.12 e Å−3 |
3605 reflections | Extinction correction: SHELXL97 (Sheldrick, 2008) |
264 parameters | Extinction coefficient: 0.0097 (13) |
0 restraints |
C22H18N2O5 | V = 1974.0 (11) Å3 |
Mr = 390.38 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.246 (3) Å | µ = 0.09 mm−1 |
b = 11.911 (4) Å | T = 296 K |
c = 17.923 (6) Å | 0.25 × 0.23 × 0.22 mm |
Bruker APEXII CCD diffractometer | 3605 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2280 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.980 | Rint = 0.033 |
8939 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.11 e Å−3 |
3605 reflections | Δρmin = −0.12 e Å−3 |
264 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 | 0.3532 (3) | 0.1353 (2) | −0.07101 (14) | 0.0662 (7) | |
C2 | 0.2883 (3) | 0.1027 (3) | −0.13739 (17) | 0.0852 (9) | |
H2 | 0.2795 | 0.0271 | −0.1496 | 0.102* | |
C3 | 0.2368 (3) | 0.1853 (4) | −0.18535 (16) | 0.0961 (11) | |
H3 | 0.1933 | 0.1658 | −0.2303 | 0.115* | |
C4 | 0.2508 (4) | 0.2945 (3) | −0.16565 (19) | 0.0956 (10) | |
H4 | 0.2173 | 0.3502 | −0.1977 | 0.115* | |
C5 | 0.3124 (3) | 0.3237 (3) | −0.10045 (17) | 0.0817 (8) | |
H5 | 0.3186 | 0.3995 | −0.0886 | 0.098* | |
C6 | 0.3665 (3) | 0.2469 (2) | −0.05063 (13) | 0.0637 (7) | |
C7 | 0.4263 (3) | 0.2894 (2) | 0.02163 (14) | 0.0747 (8) | |
H7A | 0.5196 | 0.2548 | 0.0306 | 0.090* | |
H7B | 0.4409 | 0.3698 | 0.0181 | 0.090* | |
C8 | 0.3285 (3) | 0.2649 (2) | 0.08568 (14) | 0.0648 (7) | |
C9 | 0.1744 (3) | 0.3805 (2) | 0.21269 (15) | 0.0675 (7) | |
C10 | 0.0711 (3) | 0.3651 (2) | 0.27535 (14) | 0.0613 (7) | |
C11 | −0.0023 (3) | 0.4586 (2) | 0.30155 (17) | 0.0779 (8) | |
H11 | 0.0173 | 0.5291 | 0.2817 | 0.094* | |
C12 | −0.1047 (4) | 0.4469 (3) | 0.35739 (19) | 0.0914 (10) | |
H12 | −0.1526 | 0.5098 | 0.3757 | 0.110* | |
C13 | −0.1356 (4) | 0.3429 (3) | 0.38569 (17) | 0.0914 (9) | |
H13 | −0.2047 | 0.3353 | 0.4230 | 0.110* | |
C14 | −0.0659 (3) | 0.2509 (3) | 0.35956 (16) | 0.0808 (8) | |
H14 | −0.0882 | 0.1804 | 0.3786 | 0.097* | |
C15 | 0.0376 (3) | 0.2615 (2) | 0.30509 (15) | 0.0687 (7) | |
H15 | 0.0858 | 0.1980 | 0.2880 | 0.082* | |
C16 | 0.3668 (3) | 0.2615 (2) | 0.27241 (13) | 0.0587 (6) | |
C17 | 0.4158 (3) | 0.1531 (2) | 0.26885 (16) | 0.0714 (7) | |
H17 | 0.3964 | 0.1095 | 0.2270 | 0.086* | |
C18 | 0.4936 (3) | 0.1090 (2) | 0.32708 (16) | 0.0750 (8) | |
H18 | 0.5281 | 0.0358 | 0.3236 | 0.090* | |
C19 | 0.5220 (3) | 0.1707 (2) | 0.39074 (14) | 0.0668 (7) | |
C20 | 0.4722 (3) | 0.2792 (2) | 0.39293 (15) | 0.0727 (8) | |
H20 | 0.4898 | 0.3226 | 0.4351 | 0.087* | |
C21 | 0.3968 (3) | 0.3255 (2) | 0.33402 (15) | 0.0680 (7) | |
H21 | 0.3663 | 0.3998 | 0.3361 | 0.082* | |
C22 | 0.6051 (4) | 0.1213 (3) | 0.45524 (15) | 0.0997 (11) | |
H22A | 0.5407 | 0.0785 | 0.4862 | 0.150* | |
H22B | 0.6475 | 0.1808 | 0.4841 | 0.150* | |
H22C | 0.6802 | 0.0733 | 0.4365 | 0.150* | |
N1 | 0.4064 (4) | 0.0451 (2) | −0.02206 (17) | 0.0970 (8) | |
N2 | 0.2881 (2) | 0.3064 (2) | 0.21067 (12) | 0.0713 (6) | |
O1 | 0.2230 (3) | 0.20874 (17) | 0.08620 (10) | 0.0923 (7) | |
O2 | 0.37898 (19) | 0.32093 (15) | 0.14693 (9) | 0.0750 (5) | |
O3 | 0.1555 (2) | 0.44895 (17) | 0.16349 (12) | 0.0973 (7) | |
O4 | 0.3608 (4) | −0.0472 (2) | −0.03322 (16) | 0.1591 (12) | |
O5 | 0.4911 (4) | 0.0655 (2) | 0.02581 (17) | 0.1589 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0596 (16) | 0.0736 (17) | 0.0655 (17) | 0.0017 (14) | 0.0069 (14) | 0.0037 (14) |
C2 | 0.072 (2) | 0.104 (2) | 0.080 (2) | −0.0155 (18) | 0.0139 (17) | −0.0225 (19) |
C3 | 0.0593 (19) | 0.175 (4) | 0.0541 (18) | 0.000 (2) | 0.0040 (15) | −0.003 (2) |
C4 | 0.080 (2) | 0.123 (3) | 0.084 (2) | 0.017 (2) | 0.0039 (19) | 0.026 (2) |
C5 | 0.085 (2) | 0.0853 (19) | 0.0753 (19) | 0.0026 (17) | 0.0079 (17) | 0.0145 (17) |
C6 | 0.0573 (16) | 0.0715 (17) | 0.0622 (15) | −0.0049 (14) | 0.0097 (13) | 0.0099 (14) |
C7 | 0.078 (2) | 0.0780 (17) | 0.0681 (17) | −0.0196 (15) | 0.0065 (16) | 0.0010 (14) |
C8 | 0.0636 (18) | 0.0685 (16) | 0.0624 (15) | −0.0117 (15) | −0.0025 (14) | 0.0002 (13) |
C9 | 0.0651 (19) | 0.0595 (16) | 0.0780 (18) | −0.0091 (15) | −0.0111 (15) | 0.0001 (14) |
C10 | 0.0515 (15) | 0.0589 (15) | 0.0735 (17) | 0.0002 (13) | −0.0114 (13) | −0.0039 (13) |
C11 | 0.0778 (19) | 0.0615 (16) | 0.095 (2) | 0.0096 (17) | −0.0190 (19) | −0.0074 (15) |
C12 | 0.080 (2) | 0.098 (2) | 0.096 (2) | 0.028 (2) | −0.015 (2) | −0.037 (2) |
C13 | 0.072 (2) | 0.117 (3) | 0.085 (2) | 0.006 (2) | 0.0023 (18) | −0.013 (2) |
C14 | 0.0641 (19) | 0.089 (2) | 0.090 (2) | −0.0034 (17) | 0.0018 (17) | 0.0038 (18) |
C15 | 0.0571 (18) | 0.0627 (17) | 0.0864 (18) | 0.0001 (13) | −0.0021 (15) | −0.0073 (14) |
C16 | 0.0491 (14) | 0.0635 (15) | 0.0636 (15) | −0.0052 (12) | 0.0035 (13) | −0.0056 (13) |
C17 | 0.0775 (19) | 0.0649 (17) | 0.0717 (17) | −0.0025 (15) | 0.0056 (15) | −0.0173 (14) |
C18 | 0.0778 (19) | 0.0603 (16) | 0.0869 (19) | 0.0090 (16) | 0.0150 (17) | 0.0030 (15) |
C19 | 0.0643 (17) | 0.0671 (17) | 0.0690 (17) | 0.0077 (14) | 0.0126 (15) | 0.0068 (14) |
C20 | 0.0708 (19) | 0.0748 (18) | 0.0725 (17) | 0.0015 (15) | −0.0061 (16) | −0.0120 (14) |
C21 | 0.0658 (17) | 0.0614 (15) | 0.0768 (18) | 0.0042 (15) | −0.0112 (14) | −0.0112 (13) |
C22 | 0.107 (3) | 0.114 (2) | 0.0781 (19) | 0.025 (2) | 0.0122 (19) | 0.0285 (18) |
N1 | 0.119 (2) | 0.0711 (18) | 0.101 (2) | 0.0019 (18) | 0.0082 (18) | 0.0082 (16) |
N2 | 0.0609 (14) | 0.0913 (16) | 0.0618 (13) | 0.0061 (13) | −0.0007 (12) | −0.0030 (11) |
O1 | 0.0954 (14) | 0.1119 (16) | 0.0698 (12) | −0.0502 (14) | 0.0065 (11) | −0.0052 (11) |
O2 | 0.0661 (12) | 0.0943 (13) | 0.0647 (11) | −0.0177 (11) | 0.0017 (10) | −0.0068 (10) |
O3 | 0.0899 (15) | 0.0888 (13) | 0.1131 (16) | −0.0055 (13) | −0.0006 (13) | 0.0337 (13) |
O4 | 0.238 (4) | 0.0828 (17) | 0.157 (2) | −0.020 (2) | −0.017 (3) | 0.0193 (16) |
O5 | 0.192 (3) | 0.116 (2) | 0.169 (3) | 0.001 (2) | −0.093 (3) | 0.0317 (19) |
C1—C6 | 1.384 (4) | C12—H12 | 0.9300 |
C1—C2 | 1.387 (3) | C13—C14 | 1.354 (4) |
C1—N1 | 1.472 (4) | C13—H13 | 0.9300 |
C2—C3 | 1.390 (4) | C14—C15 | 1.373 (4) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.354 (5) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.369 (4) |
C4—C5 | 1.346 (4) | C16—C21 | 1.370 (3) |
C4—H4 | 0.9300 | C16—N2 | 1.429 (3) |
C5—C6 | 1.373 (4) | C17—C18 | 1.372 (4) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.496 (3) | C18—C19 | 1.383 (4) |
C7—C8 | 1.490 (3) | C18—H18 | 0.9300 |
C7—H7A | 0.9700 | C19—C20 | 1.372 (3) |
C7—H7B | 0.9700 | C19—C22 | 1.508 (4) |
C8—O1 | 1.183 (3) | C20—C21 | 1.380 (3) |
C8—O2 | 1.367 (3) | C20—H20 | 0.9300 |
C9—O3 | 1.214 (3) | C21—H21 | 0.9300 |
C9—N2 | 1.372 (3) | C22—H22A | 0.9600 |
C9—C10 | 1.486 (4) | C22—H22B | 0.9600 |
C10—C15 | 1.379 (3) | C22—H22C | 0.9600 |
C10—C11 | 1.386 (3) | N1—O5 | 1.187 (3) |
C11—C12 | 1.385 (4) | N1—O4 | 1.194 (3) |
C11—H11 | 0.9300 | N2—O2 | 1.429 (3) |
C12—C13 | 1.369 (4) | ||
C6—C1—C2 | 122.2 (3) | C14—C13—H13 | 119.9 |
C6—C1—N1 | 120.9 (3) | C12—C13—H13 | 119.9 |
C2—C1—N1 | 116.9 (3) | C13—C14—C15 | 120.2 (3) |
C1—C2—C3 | 118.7 (3) | C13—C14—H14 | 119.9 |
C1—C2—H2 | 120.6 | C15—C14—H14 | 119.9 |
C3—C2—H2 | 120.6 | C14—C15—C10 | 120.9 (3) |
C4—C3—C2 | 119.0 (3) | C14—C15—H15 | 119.6 |
C4—C3—H3 | 120.5 | C10—C15—H15 | 119.6 |
C2—C3—H3 | 120.5 | C17—C16—C21 | 119.7 (2) |
C5—C4—C3 | 121.0 (3) | C17—C16—N2 | 119.1 (2) |
C5—C4—H4 | 119.5 | C21—C16—N2 | 121.2 (2) |
C3—C4—H4 | 119.5 | C16—C17—C18 | 119.9 (2) |
C4—C5—C6 | 123.1 (3) | C16—C17—H17 | 120.0 |
C4—C5—H5 | 118.4 | C18—C17—H17 | 120.0 |
C6—C5—H5 | 118.4 | C17—C18—C19 | 121.6 (2) |
C5—C6—C1 | 115.8 (3) | C17—C18—H18 | 119.2 |
C5—C6—C7 | 118.2 (3) | C19—C18—H18 | 119.2 |
C1—C6—C7 | 125.9 (2) | C20—C19—C18 | 117.4 (2) |
C8—C7—C6 | 112.1 (2) | C20—C19—C22 | 121.1 (3) |
C8—C7—H7A | 109.2 | C18—C19—C22 | 121.5 (2) |
C6—C7—H7A | 109.2 | C19—C20—C21 | 121.6 (3) |
C8—C7—H7B | 109.2 | C19—C20—H20 | 119.2 |
C6—C7—H7B | 109.2 | C21—C20—H20 | 119.2 |
H7A—C7—H7B | 107.9 | C16—C21—C20 | 119.8 (2) |
O1—C8—O2 | 123.5 (2) | C16—C21—H21 | 120.1 |
O1—C8—C7 | 128.1 (2) | C20—C21—H21 | 120.1 |
O2—C8—C7 | 108.4 (2) | C19—C22—H22A | 109.5 |
O3—C9—N2 | 121.5 (3) | C19—C22—H22B | 109.5 |
O3—C9—C10 | 122.6 (3) | H22A—C22—H22B | 109.5 |
N2—C9—C10 | 115.7 (2) | C19—C22—H22C | 109.5 |
C15—C10—C11 | 118.6 (3) | H22A—C22—H22C | 109.5 |
C15—C10—C9 | 123.1 (2) | H22B—C22—H22C | 109.5 |
C11—C10—C9 | 118.1 (2) | O5—N1—O4 | 122.9 (3) |
C12—C11—C10 | 119.9 (3) | O5—N1—C1 | 120.1 (3) |
C12—C11—H11 | 120.1 | O4—N1—C1 | 117.0 (3) |
C10—C11—H11 | 120.1 | C9—N2—O2 | 113.2 (2) |
C13—C12—C11 | 120.1 (3) | C9—N2—C16 | 127.6 (2) |
C13—C12—H12 | 119.9 | O2—N2—C16 | 111.39 (19) |
C11—C12—H12 | 119.9 | C8—O2—N2 | 112.48 (19) |
C14—C13—C12 | 120.3 (3) | ||
C6—C1—C2—C3 | 0.8 (4) | C21—C16—C17—C18 | 0.5 (4) |
N1—C1—C2—C3 | −179.9 (3) | N2—C16—C17—C18 | 179.0 (2) |
C1—C2—C3—C4 | −0.3 (4) | C16—C17—C18—C19 | 1.3 (4) |
C2—C3—C4—C5 | −0.6 (5) | C17—C18—C19—C20 | −1.5 (4) |
C3—C4—C5—C6 | 1.0 (5) | C17—C18—C19—C22 | 178.9 (3) |
C4—C5—C6—C1 | −0.5 (4) | C18—C19—C20—C21 | 0.0 (4) |
C4—C5—C6—C7 | −177.2 (3) | C22—C19—C20—C21 | 179.6 (3) |
C2—C1—C6—C5 | −0.4 (4) | C17—C16—C21—C20 | −2.0 (4) |
N1—C1—C6—C5 | −179.7 (3) | N2—C16—C21—C20 | 179.6 (2) |
C2—C1—C6—C7 | 176.0 (2) | C19—C20—C21—C16 | 1.8 (4) |
N1—C1—C6—C7 | −3.3 (4) | C6—C1—N1—O5 | −18.3 (5) |
C5—C6—C7—C8 | 106.5 (3) | C2—C1—N1—O5 | 162.4 (3) |
C1—C6—C7—C8 | −69.8 (4) | C6—C1—N1—O4 | 161.9 (3) |
C6—C7—C8—O1 | 8.2 (4) | C2—C1—N1—O4 | −17.4 (4) |
C6—C7—C8—O2 | −170.7 (2) | O3—C9—N2—O2 | 1.1 (3) |
O3—C9—C10—C15 | 141.9 (3) | C10—C9—N2—O2 | 176.52 (19) |
N2—C9—C10—C15 | −33.4 (3) | O3—C9—N2—C16 | 147.4 (3) |
O3—C9—C10—C11 | −33.6 (4) | C10—C9—N2—C16 | −37.2 (3) |
N2—C9—C10—C11 | 151.1 (2) | C17—C16—N2—C9 | 144.5 (3) |
C15—C10—C11—C12 | 1.2 (4) | C21—C16—N2—C9 | −37.0 (4) |
C9—C10—C11—C12 | 176.8 (2) | C17—C16—N2—O2 | −68.7 (3) |
C10—C11—C12—C13 | −1.3 (4) | C21—C16—N2—O2 | 109.7 (3) |
C11—C12—C13—C14 | 0.3 (5) | O1—C8—O2—N2 | −1.6 (4) |
C12—C13—C14—C15 | 0.8 (4) | C7—C8—O2—N2 | 177.4 (2) |
C13—C14—C15—C10 | −0.9 (4) | C9—N2—O2—C8 | −84.8 (2) |
C11—C10—C15—C14 | −0.1 (4) | C16—N2—O2—C8 | 123.4 (2) |
C9—C10—C15—C14 | −175.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O5 | 0.97 | 2.27 | 2.734 (4) | 108 |
C12—H12···O1i | 0.93 | 2.55 | 3.456 (4) | 165 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H18N2O5 |
Mr | 390.38 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 9.246 (3), 11.911 (4), 17.923 (6) |
V (Å3) | 1974.0 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.23 × 0.22 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.977, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8939, 3605, 2280 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.111, 1.01 |
No. of reflections | 3605 |
No. of parameters | 264 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.12 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O5 | 0.97 | 2.27 | 2.734 (4) | 108 |
C12—H12···O1i | 0.93 | 2.55 | 3.456 (4) | 165 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Acknowledgements
This work was supported by the Science and Technology Plan Projects of Lanzhou City (grant No. 2008-1-74)
References
Ayyangark, N. R., Hrailme, C., Kalkotf, U. R. & Srinivasan, K. V. (1986). Synth. Commun. pp. 938–941. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326–331. Web of Science CrossRef PubMed CAS Google Scholar
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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.
Hydroxamic acid derivatives have received considerable attention in recent years as the result of the discovery of their role in the biochemical toxicology of many drugs and other chemicals. Thus, these compounds continue to attract much attention as potential biological agents (Noh et al., 2009; Zeng et al., 2003).
The title compound, C22H18N2O5, was prepared according to the method described by Ayyangark et al. (1986). The molecule contains three branched chains with its centre placed at midpoint of the N2 atom (Fig. 1). The nitro-substituted benzene ring makes a dihedral angle of 71.56 (1)° with the benzoyl ring and 16.28 (1)° with the methyl-substituted benzene ring. The crystal structure features weak intra- and inter-molecular C—H···O interactions (Table 1).