organic compounds
N-(4-chlorobenzoyl)-N-(2-chlorophenyl)-O-[2-(2-nitrophenyl)acetyl]hydroxylamine
aInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China, and bGansu College of Traditional Chinese Medicine, Lanzhou 730000, Gansu Province, People's Republic of China
*Correspondence e-mail: majing.1988.ok@163.com
In the title hydroxamic acid derivate, C21H14N2O5Cl2, the nitro-substituted benzene ring forms dihedral angles of 66.0 (2) and 59.6 (2)°, with the p-chloro and o-chloro-substituted benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 64.2 (2) Å. In the crystal, weak C—H⋯O hydrogen bonds link the molecules along [010]. The crystal studied was an with refined components in the ratio 0.60 (7):0.40 (7).
Related literature
For applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the synthesis, see: Ayyangark et al. (1986). For a related structure, see: Zhang et al. (2012).
Experimental
Crystal data
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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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812040883/lh5536sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812040883/lh5536Isup2.hkl
The title compound (I) was prepared according to the method described by Ayyangark et al. (1986). Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution of (I) in dichloromethane-methanol (1:3 v/v).
Hydrogen atoms were placed in calculated positions with C—H = 0.93 and 0.97Å and included in a riding-model approximation with Uiso = 1.2Ueq(C).
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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C21H14Cl2N2O5 | F(000) = 456 |
Mr = 445.24 | Dx = 1.450 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 985 reflections |
a = 12.366 (14) Å | θ = 2.7–19.2° |
b = 6.789 (8) Å | µ = 0.36 mm−1 |
c = 12.579 (14) Å | T = 296 K |
β = 105.150 (14)° | Block, colorless |
V = 1019 (2) Å3 | 0.21 × 0.20 × 0.16 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 3669 independent reflections |
Radiation source: fine-focus sealed tube | 1821 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.929, Tmax = 0.945 | k = −8→8 |
5091 measured reflections | l = −15→14 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0117P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.054 | (Δ/σ)max < 0.001 |
wR(F2) = 0.069 | Δρmax = 0.17 e Å−3 |
S = 0.99 | Δρmin = −0.16 e Å−3 |
3669 reflections | Absolute structure: Flack (1983), 1624 Friedel pairs |
271 parameters | Absolute structure parameter: 0.40 (7) |
1 restraint |
C21H14Cl2N2O5 | V = 1019 (2) Å3 |
Mr = 445.24 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.366 (14) Å | µ = 0.36 mm−1 |
b = 6.789 (8) Å | T = 296 K |
c = 12.579 (14) Å | 0.21 × 0.20 × 0.16 mm |
β = 105.150 (14)° |
Bruker APEXII CCD diffractometer | 3669 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1821 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.945 | Rint = 0.030 |
5091 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.069 | Δρmax = 0.17 e Å−3 |
S = 0.99 | Δρmin = −0.16 e Å−3 |
3669 reflections | Absolute structure: Flack (1983), 1624 Friedel pairs |
271 parameters | Absolute structure parameter: 0.40 (7) |
1 restraint |
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 | 0.0147 (3) | 0.5015 (8) | 0.8371 (3) | 0.0556 (12) | |
H1 | 0.0422 | 0.4007 | 0.8869 | 0.067* | |
C2 | −0.0321 (4) | 0.6675 (7) | 0.8709 (3) | 0.0590 (13) | |
H2 | −0.0363 | 0.6786 | 0.9434 | 0.071* | |
C3 | −0.0720 (4) | 0.8152 (6) | 0.7973 (4) | 0.0581 (14) | |
C4 | −0.0663 (4) | 0.8041 (7) | 0.6904 (4) | 0.0642 (15) | |
H4 | −0.0935 | 0.9061 | 0.6414 | 0.077* | |
C5 | −0.0194 (4) | 0.6382 (7) | 0.6562 (4) | 0.0554 (13) | |
H5 | −0.0148 | 0.6292 | 0.5838 | 0.067* | |
C6 | 0.0207 (3) | 0.4855 (7) | 0.7292 (3) | 0.0439 (11) | |
C7 | 0.0602 (4) | 0.3045 (7) | 0.6835 (4) | 0.0493 (13) | |
C8 | 0.2401 (3) | 0.3019 (7) | 0.8323 (4) | 0.0487 (12) | |
C9 | 0.2722 (4) | 0.2095 (7) | 0.9344 (4) | 0.0577 (13) | |
C10 | 0.3508 (4) | 0.2985 (10) | 1.0199 (5) | 0.0814 (17) | |
H10 | 0.3720 | 0.2376 | 1.0884 | 0.098* | |
C11 | 0.3970 (4) | 0.4729 (11) | 1.0044 (5) | 0.0906 (19) | |
H11 | 0.4484 | 0.5328 | 1.0628 | 0.109* | |
C12 | 0.3684 (4) | 0.5626 (8) | 0.9024 (5) | 0.0831 (18) | |
H12 | 0.4026 | 0.6801 | 0.8915 | 0.100* | |
C13 | 0.2899 (4) | 0.4789 (8) | 0.8174 (4) | 0.0640 (14) | |
H13 | 0.2697 | 0.5411 | 0.7492 | 0.077* | |
C14 | 0.2324 (3) | 0.0798 (8) | 0.6138 (4) | 0.0493 (13) | |
C15 | 0.2469 (3) | −0.1148 (6) | 0.5610 (3) | 0.0523 (12) | |
H15A | 0.2688 | −0.2138 | 0.6182 | 0.063* | |
H15B | 0.1754 | −0.1543 | 0.5128 | 0.063* | |
C16 | 0.3330 (4) | −0.1087 (6) | 0.4954 (4) | 0.0494 (12) | |
C17 | 0.2956 (4) | −0.1148 (7) | 0.3812 (4) | 0.0669 (14) | |
H17 | 0.2190 | −0.1217 | 0.3485 | 0.080* | |
C18 | 0.3679 (5) | −0.1107 (8) | 0.3152 (4) | 0.0791 (16) | |
H18 | 0.3406 | −0.1116 | 0.2390 | 0.095* | |
C19 | 0.4823 (5) | −0.1054 (7) | 0.3634 (5) | 0.0778 (16) | |
H19 | 0.5320 | −0.1053 | 0.3191 | 0.093* | |
C20 | 0.5227 (4) | −0.1003 (7) | 0.4756 (5) | 0.0690 (14) | |
H20 | 0.5994 | −0.0966 | 0.5082 | 0.083* | |
C21 | 0.4474 (4) | −0.1006 (6) | 0.5391 (4) | 0.0511 (12) | |
Cl1 | −0.13093 (10) | 1.0228 (2) | 0.84135 (10) | 0.0924 (4) | |
Cl2 | 0.21125 (11) | −0.0100 (2) | 0.95615 (10) | 0.0868 (4) | |
N1 | 0.1548 (3) | 0.2169 (6) | 0.7465 (3) | 0.0501 (9) | |
N2 | 0.4985 (4) | −0.0959 (6) | 0.6589 (4) | 0.0711 (13) | |
O1 | 0.0103 (2) | 0.2380 (4) | 0.5951 (2) | 0.0622 (9) | |
O2 | 0.1866 (2) | 0.0409 (4) | 0.7008 (2) | 0.0563 (8) | |
O3 | 0.4389 (3) | −0.0664 (6) | 0.7204 (3) | 0.0983 (14) | |
O4 | 0.5971 (3) | −0.1181 (7) | 0.6925 (3) | 0.1191 (16) | |
O5 | 0.2537 (2) | 0.2392 (5) | 0.5864 (2) | 0.0613 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.062 (3) | 0.066 (3) | 0.040 (3) | 0.008 (3) | 0.015 (2) | 0.012 (3) |
C2 | 0.068 (3) | 0.077 (4) | 0.035 (3) | 0.006 (3) | 0.017 (3) | 0.005 (3) |
C3 | 0.053 (3) | 0.053 (3) | 0.062 (4) | −0.007 (3) | 0.005 (3) | −0.006 (3) |
C4 | 0.068 (4) | 0.065 (4) | 0.048 (4) | −0.012 (3) | −0.006 (3) | 0.005 (3) |
C5 | 0.063 (4) | 0.070 (4) | 0.035 (3) | −0.020 (3) | 0.016 (3) | −0.002 (3) |
C6 | 0.038 (3) | 0.058 (3) | 0.035 (3) | −0.005 (3) | 0.007 (2) | 0.007 (3) |
C7 | 0.050 (3) | 0.068 (4) | 0.036 (3) | −0.006 (3) | 0.022 (3) | 0.003 (3) |
C8 | 0.029 (3) | 0.071 (4) | 0.043 (3) | 0.003 (3) | 0.005 (3) | −0.008 (3) |
C9 | 0.046 (3) | 0.065 (3) | 0.061 (3) | 0.011 (3) | 0.010 (3) | 0.001 (3) |
C10 | 0.067 (4) | 0.103 (5) | 0.061 (4) | 0.024 (4) | −0.007 (3) | −0.005 (4) |
C11 | 0.076 (4) | 0.108 (6) | 0.074 (4) | 0.011 (5) | −0.006 (3) | −0.012 (5) |
C12 | 0.055 (4) | 0.083 (5) | 0.104 (5) | −0.008 (4) | 0.008 (3) | −0.004 (4) |
C13 | 0.049 (3) | 0.082 (4) | 0.057 (3) | −0.009 (3) | 0.007 (3) | 0.012 (3) |
C14 | 0.031 (3) | 0.076 (4) | 0.042 (3) | −0.004 (3) | 0.011 (2) | 0.000 (3) |
C15 | 0.042 (3) | 0.059 (3) | 0.055 (3) | −0.001 (3) | 0.010 (2) | −0.006 (3) |
C16 | 0.040 (3) | 0.042 (3) | 0.068 (4) | 0.007 (3) | 0.017 (3) | −0.004 (3) |
C17 | 0.067 (4) | 0.082 (3) | 0.051 (3) | 0.009 (3) | 0.013 (3) | −0.011 (3) |
C18 | 0.101 (5) | 0.082 (4) | 0.063 (4) | 0.014 (4) | 0.036 (4) | −0.003 (3) |
C19 | 0.083 (5) | 0.055 (3) | 0.114 (5) | 0.009 (4) | 0.059 (4) | −0.005 (4) |
C20 | 0.050 (3) | 0.050 (3) | 0.110 (5) | −0.003 (3) | 0.025 (3) | −0.012 (4) |
C21 | 0.049 (3) | 0.038 (3) | 0.069 (4) | −0.001 (3) | 0.019 (3) | 0.000 (3) |
Cl1 | 0.0909 (10) | 0.0798 (10) | 0.0966 (10) | 0.0165 (10) | 0.0068 (8) | −0.0179 (9) |
Cl2 | 0.1014 (10) | 0.0849 (11) | 0.0788 (9) | 0.0064 (10) | 0.0320 (7) | 0.0200 (9) |
N1 | 0.040 (2) | 0.065 (3) | 0.044 (2) | 0.003 (2) | 0.009 (2) | −0.006 (2) |
N2 | 0.060 (4) | 0.059 (3) | 0.083 (4) | −0.002 (3) | −0.002 (3) | −0.004 (3) |
O1 | 0.057 (2) | 0.088 (2) | 0.0363 (19) | 0.001 (2) | 0.0039 (16) | −0.0121 (18) |
O2 | 0.0591 (19) | 0.060 (2) | 0.0549 (19) | −0.0036 (19) | 0.0230 (16) | −0.0048 (18) |
O3 | 0.073 (3) | 0.146 (4) | 0.067 (3) | 0.002 (3) | 0.003 (2) | 0.003 (3) |
O4 | 0.056 (2) | 0.155 (4) | 0.124 (3) | 0.012 (3) | −0.016 (2) | −0.003 (3) |
O5 | 0.063 (2) | 0.062 (2) | 0.067 (2) | −0.006 (2) | 0.0312 (18) | 0.0019 (18) |
C1—C6 | 1.382 (5) | C12—C13 | 1.366 (5) |
C1—C2 | 1.384 (6) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.366 (6) | C14—O5 | 1.186 (5) |
C2—H2 | 0.9300 | C14—O2 | 1.384 (5) |
C3—C4 | 1.367 (5) | C14—C15 | 1.510 (6) |
C3—Cl1 | 1.742 (5) | C15—C16 | 1.509 (5) |
C4—C5 | 1.386 (5) | C15—H15A | 0.9700 |
C4—H4 | 0.9300 | C15—H15B | 0.9700 |
C5—C6 | 1.388 (5) | C16—C21 | 1.379 (5) |
C5—H5 | 0.9300 | C16—C17 | 1.390 (5) |
C6—C7 | 1.492 (6) | C17—C18 | 1.370 (6) |
C7—O1 | 1.209 (5) | C17—H17 | 0.9300 |
C7—N1 | 1.367 (5) | C18—C19 | 1.386 (6) |
C8—C13 | 1.385 (5) | C18—H18 | 0.9300 |
C8—C9 | 1.391 (5) | C19—C20 | 1.369 (6) |
C8—N1 | 1.419 (5) | C19—H19 | 0.9300 |
C9—C10 | 1.386 (6) | C20—C21 | 1.378 (5) |
C9—Cl2 | 1.724 (5) | C20—H20 | 0.9300 |
C10—C11 | 1.351 (6) | C21—N2 | 1.474 (6) |
C10—H10 | 0.9300 | N1—O2 | 1.426 (4) |
C11—C12 | 1.381 (6) | N2—O4 | 1.191 (5) |
C11—H11 | 0.9300 | N2—O3 | 1.216 (4) |
C6—C1—C2 | 120.0 (4) | C12—C13—H13 | 119.8 |
C6—C1—H1 | 120.0 | C8—C13—H13 | 119.8 |
C2—C1—H1 | 120.0 | O5—C14—O2 | 124.9 (5) |
C3—C2—C1 | 119.8 (4) | O5—C14—C15 | 127.6 (4) |
C3—C2—H2 | 120.1 | O2—C14—C15 | 107.5 (4) |
C1—C2—H2 | 120.1 | C16—C15—C14 | 113.5 (4) |
C2—C3—C4 | 121.5 (4) | C16—C15—H15A | 108.9 |
C2—C3—Cl1 | 119.1 (4) | C14—C15—H15A | 108.9 |
C4—C3—Cl1 | 119.4 (4) | C16—C15—H15B | 108.9 |
C3—C4—C5 | 118.9 (4) | C14—C15—H15B | 108.9 |
C3—C4—H4 | 120.5 | H15A—C15—H15B | 107.7 |
C5—C4—H4 | 120.5 | C21—C16—C17 | 116.3 (4) |
C4—C5—C6 | 120.5 (4) | C21—C16—C15 | 125.5 (4) |
C4—C5—H5 | 119.7 | C17—C16—C15 | 118.3 (4) |
C6—C5—H5 | 119.7 | C18—C17—C16 | 122.2 (5) |
C1—C6—C5 | 119.3 (5) | C18—C17—H17 | 118.9 |
C1—C6—C7 | 123.4 (5) | C16—C17—H17 | 118.9 |
C5—C6—C7 | 117.2 (4) | C17—C18—C19 | 119.3 (5) |
O1—C7—N1 | 121.7 (4) | C17—C18—H18 | 120.4 |
O1—C7—C6 | 121.5 (4) | C19—C18—H18 | 120.4 |
N1—C7—C6 | 116.8 (4) | C20—C19—C18 | 120.5 (5) |
C13—C8—C9 | 119.1 (4) | C20—C19—H19 | 119.8 |
C13—C8—N1 | 121.2 (4) | C18—C19—H19 | 119.8 |
C9—C8—N1 | 119.6 (5) | C19—C20—C21 | 118.6 (5) |
C10—C9—C8 | 119.5 (5) | C19—C20—H20 | 120.7 |
C10—C9—Cl2 | 120.1 (5) | C21—C20—H20 | 120.7 |
C8—C9—Cl2 | 120.4 (4) | C20—C21—C16 | 123.2 (5) |
C11—C10—C9 | 120.5 (6) | C20—C21—N2 | 114.8 (5) |
C11—C10—H10 | 119.7 | C16—C21—N2 | 122.0 (4) |
C9—C10—H10 | 119.7 | C7—N1—C8 | 128.2 (4) |
C10—C11—C12 | 120.3 (6) | C7—N1—O2 | 114.5 (3) |
C10—C11—H11 | 119.8 | C8—N1—O2 | 114.8 (3) |
C12—C11—H11 | 119.8 | O4—N2—O3 | 122.0 (5) |
C13—C12—C11 | 120.1 (6) | O4—N2—C21 | 119.0 (5) |
C13—C12—H12 | 120.0 | O3—N2—C21 | 118.9 (4) |
C11—C12—H12 | 120.0 | C14—O2—N1 | 111.9 (3) |
C12—C13—C8 | 120.4 (4) | ||
C6—C1—C2—C3 | −0.1 (7) | C14—C15—C16—C17 | −107.7 (5) |
C1—C2—C3—C4 | −0.5 (7) | C21—C16—C17—C18 | −0.7 (7) |
C1—C2—C3—Cl1 | 179.9 (3) | C15—C16—C17—C18 | −179.7 (4) |
C2—C3—C4—C5 | 0.4 (7) | C16—C17—C18—C19 | 1.6 (8) |
Cl1—C3—C4—C5 | −180.0 (3) | C17—C18—C19—C20 | −1.3 (8) |
C3—C4—C5—C6 | 0.3 (7) | C18—C19—C20—C21 | 0.0 (8) |
C2—C1—C6—C5 | 0.7 (6) | C19—C20—C21—C16 | 1.0 (7) |
C2—C1—C6—C7 | −174.2 (4) | C19—C20—C21—N2 | 179.7 (4) |
C4—C5—C6—C1 | −0.8 (6) | C17—C16—C21—C20 | −0.6 (7) |
C4—C5—C6—C7 | 174.4 (4) | C15—C16—C21—C20 | 178.3 (4) |
C1—C6—C7—O1 | 134.5 (4) | C17—C16—C21—N2 | −179.3 (4) |
C5—C6—C7—O1 | −40.6 (6) | C15—C16—C21—N2 | −0.3 (7) |
C1—C6—C7—N1 | −45.1 (5) | O1—C7—N1—C8 | 159.2 (4) |
C5—C6—C7—N1 | 139.9 (4) | C6—C7—N1—C8 | −21.3 (6) |
C13—C8—C9—C10 | 1.7 (6) | O1—C7—N1—O2 | −1.6 (5) |
N1—C8—C9—C10 | −176.3 (4) | C6—C7—N1—O2 | 177.9 (3) |
C13—C8—C9—Cl2 | 179.5 (3) | C13—C8—N1—C7 | −49.9 (6) |
N1—C8—C9—Cl2 | 1.5 (6) | C9—C8—N1—C7 | 128.1 (4) |
C8—C9—C10—C11 | −0.5 (7) | C13—C8—N1—O2 | 110.9 (4) |
Cl2—C9—C10—C11 | −178.4 (4) | C9—C8—N1—O2 | −71.2 (5) |
C9—C10—C11—C12 | −1.5 (8) | C20—C21—N2—O4 | −9.7 (7) |
C10—C11—C12—C13 | 2.5 (8) | C16—C21—N2—O4 | 169.1 (5) |
C11—C12—C13—C8 | −1.3 (7) | C20—C21—N2—O3 | 169.2 (4) |
C9—C8—C13—C12 | −0.8 (6) | C16—C21—N2—O3 | −12.1 (7) |
N1—C8—C13—C12 | 177.2 (4) | O5—C14—O2—N1 | 7.0 (6) |
O5—C14—C15—C16 | 23.1 (6) | C15—C14—O2—N1 | −171.7 (3) |
O2—C14—C15—C16 | −158.2 (3) | C7—N1—O2—C14 | 74.1 (4) |
C14—C15—C16—C21 | 73.3 (6) | C8—N1—O2—C14 | −89.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.38 | 3.264 (7) | 158 |
C15—H15B···O1ii | 0.97 | 2.45 | 3.421 (6) | 175 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H14Cl2N2O5 |
Mr | 445.24 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 12.366 (14), 6.789 (8), 12.579 (14) |
β (°) | 105.150 (14) |
V (Å3) | 1019 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.21 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.929, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5091, 3669, 1821 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.069, 0.99 |
No. of reflections | 3669 |
No. of parameters | 271 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Absolute structure | Flack (1983), 1624 Friedel pairs |
Absolute structure parameter | 0.40 (7) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.38 | 3.264 (7) | 158 |
C15—H15B···O1ii | 0.97 | 2.45 | 3.421 (6) | 175 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1. |
Acknowledgements
This work was supported by the Natural Science Fund Projects of Gansu Province (0710RJZA124).
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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 (Noh et al., 2009; Zeng et al., 2003). The molecular structure of the title compound is sjown in Fig. 1. The nitro-substituted benzene ring (C16-C24) forms dihedral angles of 66.0 (2) and 59.6 (2)°, with the 4-chloro (C1-C6) and 2-chloro-substituted (C8-C13) benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings (C1-6/C8-C13) is 64.2 (2)Å. In the crystal, weak C—H···O hydrogen bonds linke molecules along [010] (Fig .2). The bond legths and angles can be compared to those in N-(2-Chlorophenyl)-1-phenylformamido 3-(2-nitrophenyl)propanoate (Zhang et al., 2012).