organic compounds
N-(2-Chlorophenyl)-1-(4-chlorophenyl)formamido 3-(2-nitrophenyl)propanoate
aDepartment of Laboratory Center for Medical Sciences, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China, bJiuquan Institute for Food and Drug Control, Jiuquan 735000, Gansu Province, People's Republic of China, and cInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China
*Correspondence e-mail: fanlinlan1020@163.com
In the title hydroxamic acid derivative, C22H16Cl2N2O5, the nitro-substituted benzene ring forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the 4-chloro- and 2-chloro-substituted benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 68.19 (13)°. The O atoms of the nitro group were refined as disordered over two sets of sites with equal occupancies. In the crystal, weak C—H⋯O(=C) hydrogen bonds link molecules along [100].
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 related structures, see: Zhang et al. (2012); Ma et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536812048726/lh5558sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048726/lh5558Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048726/lh5558Isup3.cml
The title compound (I) was prepared according to the method described by Ayyangark et al. (1986). Crystals of (I) 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(H) = 1.2Ueq(C). The O atoms of the nitro group were refined as disorderd over two sets of sites (O4A,O5A/O4B,O5B) with equal occupancies. No geometric constraints were applied to the N—O distances or O—N—O angles as this had a negative effect on the refinment. The O atoms were restrained to be isotropic in nature, using ISOR 0.01 0.02 O4B O5A O5A O4A in SHELXL (Sheldrick, 2008).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).C22H16Cl2N2O5 | Z = 2 |
Mr = 459.27 | F(000) = 472 |
Triclinic, P1 | Dx = 1.443 Mg m−3 |
a = 9.1574 (8) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 10.1976 (6) Å | Cell parameters from 2906 reflections |
c = 12.1736 (8) Å | θ = 3.0–28.5° |
α = 91.847 (5)° | µ = 0.34 mm−1 |
β = 108.327 (8)° | T = 293 K |
γ = 100.285 (6)° | Block, colourless |
V = 1057.06 (13) Å3 | 0.32 × 0.28 × 0.25 mm |
Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer | 4785 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3434 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.018 |
Detector resolution: 16.0733 pixels mm-1 | θmax = 28.6°, θmin = 3.0° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −11→13 |
Tmin = 0.843, Tmax = 1.000 | l = −12→15 |
7898 measured reflections |
Refinement on F2 | 24 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.5564P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.139 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.48 e Å−3 |
4785 reflections | Δρmin = −0.45 e Å−3 |
298 parameters |
C22H16Cl2N2O5 | γ = 100.285 (6)° |
Mr = 459.27 | V = 1057.06 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.1574 (8) Å | Mo Kα radiation |
b = 10.1976 (6) Å | µ = 0.34 mm−1 |
c = 12.1736 (8) Å | T = 293 K |
α = 91.847 (5)° | 0.32 × 0.28 × 0.25 mm |
β = 108.327 (8)° |
Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer | 4785 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3434 reflections with I > 2σ(I) |
Tmin = 0.843, Tmax = 1.000 | Rint = 0.018 |
7898 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 24 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.48 e Å−3 |
4785 reflections | Δρmin = −0.45 e Å−3 |
298 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 | Occ. (<1) | |
Cl1 | 0.30250 (8) | 0.14141 (7) | 0.49104 (6) | 0.0635 (2) | |
Cl2 | 0.24622 (12) | −0.53403 (8) | 0.43213 (9) | 0.0942 (3) | |
O2 | 0.03359 (18) | 0.18128 (15) | 0.24969 (15) | 0.0496 (4) | |
O1 | −0.1073 (2) | −0.01016 (18) | 0.33664 (18) | 0.0641 (5) | |
O3 | −0.1782 (3) | 0.0981 (2) | 0.09403 (19) | 0.0827 (7) | |
N1 | 0.0768 (2) | 0.05360 (18) | 0.25036 (18) | 0.0455 (5) | |
C9 | 0.3548 (3) | 0.1106 (2) | 0.3701 (2) | 0.0473 (5) | |
C8 | 0.2407 (3) | 0.0716 (2) | 0.2637 (2) | 0.0436 (5) | |
C7 | 0.0030 (3) | −0.0337 (2) | 0.3102 (2) | 0.0468 (5) | |
C6 | 0.0626 (3) | −0.1603 (2) | 0.3349 (2) | 0.0456 (5) | |
C3 | 0.1726 (3) | −0.3910 (2) | 0.3938 (3) | 0.0583 (7) | |
C14 | −0.0991 (3) | 0.1893 (3) | 0.1623 (2) | 0.0532 (6) | |
C13 | 0.2822 (3) | 0.0474 (3) | 0.1654 (3) | 0.0576 (7) | |
H13 | 0.2058 | 0.0246 | 0.0927 | 0.069* | |
C4 | 0.1748 (3) | −0.3425 (2) | 0.2910 (3) | 0.0600 (7) | |
H4 | 0.2127 | −0.3874 | 0.2414 | 0.072* | |
C17 | −0.3174 (3) | 0.4808 (3) | 0.1221 (2) | 0.0558 (7) | |
C1 | 0.0565 (3) | −0.2147 (3) | 0.4362 (2) | 0.0565 (6) | |
H1 | 0.0148 | −0.1728 | 0.4849 | 0.068* | |
C5 | 0.1203 (3) | −0.2260 (2) | 0.2610 (2) | 0.0538 (6) | |
H5 | 0.1223 | −0.1919 | 0.1915 | 0.065* | |
C18 | −0.2762 (3) | 0.6005 (3) | 0.0793 (2) | 0.0594 (7) | |
C15 | −0.1275 (3) | 0.3281 (2) | 0.1738 (2) | 0.0545 (6) | |
H15A | −0.0445 | 0.3904 | 0.1583 | 0.065* | |
H15B | −0.1223 | 0.3501 | 0.2532 | 0.065* | |
N2 | −0.1934 (4) | 0.6103 (4) | −0.0050 (3) | 0.0862 (8) | |
C11 | 0.5514 (4) | 0.0928 (3) | 0.2855 (4) | 0.0758 (9) | |
H11 | 0.6565 | 0.0978 | 0.2930 | 0.091* | |
C12 | 0.4391 (4) | 0.0577 (3) | 0.1778 (3) | 0.0731 (9) | |
H12 | 0.4689 | 0.0409 | 0.1132 | 0.088* | |
C10 | 0.5115 (3) | 0.1204 (3) | 0.3813 (3) | 0.0634 (7) | |
H10 | 0.5887 | 0.1455 | 0.4533 | 0.076* | |
C2 | 0.1111 (3) | −0.3299 (3) | 0.4659 (3) | 0.0642 (7) | |
H2 | 0.1064 | −0.3660 | 0.5342 | 0.077* | |
C16 | −0.2842 (3) | 0.3464 (3) | 0.0924 (3) | 0.0670 (8) | |
H16A | −0.2836 | 0.3403 | 0.0129 | 0.080* | |
H16B | −0.3667 | 0.2756 | 0.0986 | 0.080* | |
C20 | −0.3816 (4) | 0.7203 (4) | 0.1959 (3) | 0.0823 (10) | |
H20 | −0.4026 | 0.7998 | 0.2210 | 0.099* | |
C22 | −0.3929 (4) | 0.4867 (3) | 0.2037 (3) | 0.0744 (8) | |
H22 | −0.4229 | 0.4084 | 0.2350 | 0.089* | |
C21 | −0.4252 (4) | 0.6038 (4) | 0.2402 (3) | 0.0854 (10) | |
H21 | −0.4768 | 0.6038 | 0.2949 | 0.102* | |
C19 | −0.3082 (4) | 0.7198 (3) | 0.1157 (3) | 0.0744 (9) | |
H19 | −0.2790 | 0.7987 | 0.0850 | 0.089* | |
O4B | −0.2146 (9) | 0.5291 (11) | −0.0774 (8) | 0.137 (4) | 0.50 |
O5A | −0.2098 (13) | 0.6859 (11) | −0.0663 (10) | 0.171 (4) | 0.50 |
O4A | −0.1345 (10) | 0.5136 (9) | −0.0205 (7) | 0.114 (3) | 0.50 |
O5B | −0.0987 (8) | 0.7288 (7) | −0.0029 (5) | 0.0943 (17) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0684 (4) | 0.0682 (4) | 0.0530 (4) | 0.0221 (3) | 0.0142 (3) | 0.0018 (3) |
Cl2 | 0.1052 (7) | 0.0560 (4) | 0.1179 (8) | 0.0351 (4) | 0.0201 (6) | 0.0158 (5) |
O2 | 0.0434 (9) | 0.0434 (8) | 0.0577 (10) | 0.0202 (7) | 0.0046 (7) | 0.0009 (7) |
O1 | 0.0492 (10) | 0.0645 (11) | 0.0909 (14) | 0.0216 (9) | 0.0346 (10) | 0.0043 (10) |
O3 | 0.0803 (14) | 0.0757 (13) | 0.0724 (14) | 0.0383 (11) | −0.0127 (11) | −0.0204 (11) |
N1 | 0.0394 (10) | 0.0423 (10) | 0.0578 (12) | 0.0189 (8) | 0.0140 (9) | 0.0052 (9) |
C9 | 0.0416 (12) | 0.0391 (11) | 0.0630 (15) | 0.0134 (9) | 0.0159 (11) | 0.0125 (11) |
C8 | 0.0388 (12) | 0.0397 (11) | 0.0571 (14) | 0.0161 (9) | 0.0171 (10) | 0.0110 (10) |
C7 | 0.0368 (12) | 0.0475 (12) | 0.0557 (14) | 0.0117 (10) | 0.0133 (10) | −0.0034 (11) |
C6 | 0.0340 (11) | 0.0407 (11) | 0.0608 (15) | 0.0053 (9) | 0.0154 (10) | −0.0026 (10) |
C3 | 0.0549 (15) | 0.0398 (12) | 0.0733 (19) | 0.0091 (11) | 0.0117 (13) | 0.0022 (12) |
C14 | 0.0477 (14) | 0.0620 (15) | 0.0497 (14) | 0.0255 (12) | 0.0079 (11) | 0.0009 (12) |
C13 | 0.0608 (16) | 0.0535 (14) | 0.0696 (18) | 0.0201 (12) | 0.0311 (14) | 0.0147 (13) |
C4 | 0.0606 (16) | 0.0457 (13) | 0.080 (2) | 0.0152 (12) | 0.0298 (14) | −0.0048 (13) |
C17 | 0.0432 (13) | 0.0602 (15) | 0.0573 (15) | 0.0255 (12) | −0.0009 (11) | 0.0024 (12) |
C1 | 0.0568 (15) | 0.0526 (14) | 0.0655 (17) | 0.0093 (12) | 0.0289 (13) | 0.0018 (12) |
C5 | 0.0560 (15) | 0.0455 (13) | 0.0635 (16) | 0.0116 (11) | 0.0243 (12) | 0.0003 (11) |
C18 | 0.0480 (14) | 0.0698 (17) | 0.0559 (16) | 0.0250 (13) | 0.0032 (12) | 0.0071 (13) |
C15 | 0.0506 (14) | 0.0529 (14) | 0.0571 (15) | 0.0240 (11) | 0.0064 (11) | 0.0015 (12) |
N2 | 0.088 (2) | 0.106 (2) | 0.071 (2) | 0.037 (2) | 0.0235 (16) | 0.026 (2) |
C11 | 0.0516 (17) | 0.0695 (18) | 0.122 (3) | 0.0229 (14) | 0.0430 (19) | 0.0298 (19) |
C12 | 0.086 (2) | 0.0659 (18) | 0.098 (3) | 0.0309 (16) | 0.063 (2) | 0.0240 (17) |
C10 | 0.0421 (14) | 0.0575 (15) | 0.089 (2) | 0.0134 (12) | 0.0159 (14) | 0.0201 (15) |
C2 | 0.0716 (18) | 0.0520 (15) | 0.0662 (18) | 0.0074 (13) | 0.0209 (15) | 0.0079 (13) |
C16 | 0.0606 (17) | 0.0610 (16) | 0.0701 (18) | 0.0311 (13) | −0.0015 (14) | 0.0003 (14) |
C20 | 0.070 (2) | 0.080 (2) | 0.089 (2) | 0.0403 (18) | 0.0030 (18) | −0.0141 (19) |
C22 | 0.0614 (18) | 0.084 (2) | 0.084 (2) | 0.0323 (16) | 0.0222 (16) | 0.0157 (17) |
C21 | 0.070 (2) | 0.111 (3) | 0.083 (2) | 0.045 (2) | 0.0217 (18) | −0.001 (2) |
C19 | 0.0672 (19) | 0.0629 (17) | 0.082 (2) | 0.0270 (15) | 0.0005 (16) | 0.0067 (16) |
O4B | 0.106 (6) | 0.178 (8) | 0.124 (7) | −0.001 (5) | 0.055 (5) | −0.074 (6) |
O5A | 0.222 (9) | 0.153 (7) | 0.193 (8) | 0.065 (7) | 0.119 (7) | 0.114 (7) |
O4A | 0.140 (7) | 0.131 (5) | 0.124 (6) | 0.071 (5) | 0.087 (5) | 0.062 (5) |
O5B | 0.111 (5) | 0.096 (4) | 0.082 (4) | 0.012 (3) | 0.042 (3) | 0.027 (3) |
Cl1—C9 | 1.721 (3) | C5—H5 | 0.9300 |
Cl2—C3 | 1.731 (3) | C18—N2 | 1.451 (4) |
O2—N1 | 1.426 (2) | C18—C19 | 1.391 (4) |
O2—C14 | 1.357 (3) | C15—H15A | 0.9700 |
O1—C7 | 1.211 (3) | C15—H15B | 0.9700 |
O3—C14 | 1.189 (3) | C15—C16 | 1.513 (3) |
N1—C8 | 1.436 (3) | N2—O4B | 1.135 (8) |
N1—C7 | 1.385 (3) | N2—O5A | 1.087 (8) |
C9—C8 | 1.377 (3) | N2—O4A | 1.241 (8) |
C9—C10 | 1.383 (3) | N2—O5B | 1.350 (7) |
C8—C13 | 1.392 (4) | C11—H11 | 0.9300 |
C7—C6 | 1.492 (3) | C11—C12 | 1.377 (5) |
C6—C1 | 1.381 (4) | C11—C10 | 1.363 (4) |
C6—C5 | 1.387 (3) | C12—H12 | 0.9300 |
C3—C4 | 1.365 (4) | C10—H10 | 0.9300 |
C3—C2 | 1.370 (4) | C2—H2 | 0.9300 |
C14—C15 | 1.494 (3) | C16—H16A | 0.9700 |
C13—H13 | 0.9300 | C16—H16B | 0.9700 |
C13—C12 | 1.380 (4) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.367 (5) |
C4—C5 | 1.385 (3) | C20—C19 | 1.348 (5) |
C17—C18 | 1.380 (4) | C22—H22 | 0.9300 |
C17—C16 | 1.512 (3) | C22—C21 | 1.373 (4) |
C17—C22 | 1.383 (4) | C21—H21 | 0.9300 |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C1—C2 | 1.372 (4) | ||
C14—O2—N1 | 114.19 (17) | H15A—C15—H15B | 107.7 |
O2—N1—C8 | 109.22 (16) | C16—C15—H15A | 108.9 |
C7—N1—O2 | 112.21 (17) | C16—C15—H15B | 108.9 |
C7—N1—C8 | 123.88 (18) | O4B—N2—C18 | 123.7 (6) |
C8—C9—Cl1 | 120.05 (18) | O4B—N2—O5B | 119.1 (6) |
C8—C9—C10 | 120.3 (3) | O5A—N2—C18 | 119.8 (6) |
C10—C9—Cl1 | 119.6 (2) | O5A—N2—O4B | 91.5 (9) |
C9—C8—N1 | 121.6 (2) | O5A—N2—O4A | 121.4 (7) |
C9—C8—C13 | 120.4 (2) | O5A—N2—O5B | 50.8 (6) |
C13—C8—N1 | 118.0 (2) | O4A—N2—C18 | 116.9 (4) |
O1—C7—N1 | 121.4 (2) | O4A—N2—O5B | 112.4 (6) |
O1—C7—C6 | 122.4 (2) | O5B—N2—C18 | 116.9 (4) |
N1—C7—C6 | 116.12 (19) | C12—C11—H11 | 119.4 |
C1—C6—C7 | 117.4 (2) | C10—C11—H11 | 119.4 |
C1—C6—C5 | 119.0 (2) | C10—C11—C12 | 121.3 (3) |
C5—C6—C7 | 123.5 (2) | C13—C12—H12 | 119.9 |
C4—C3—Cl2 | 119.1 (2) | C11—C12—C13 | 120.2 (3) |
C4—C3—C2 | 121.3 (2) | C11—C12—H12 | 119.9 |
C2—C3—Cl2 | 119.6 (2) | C9—C10—H10 | 120.4 |
O2—C14—C15 | 107.5 (2) | C11—C10—C9 | 119.1 (3) |
O3—C14—O2 | 124.2 (2) | C11—C10—H10 | 120.4 |
O3—C14—C15 | 128.2 (2) | C3—C2—C1 | 119.2 (3) |
C8—C13—H13 | 120.6 | C3—C2—H2 | 120.4 |
C12—C13—C8 | 118.7 (3) | C1—C2—H2 | 120.4 |
C12—C13—H13 | 120.6 | C17—C16—C15 | 110.6 (2) |
C3—C4—H4 | 120.2 | C17—C16—H16A | 109.5 |
C3—C4—C5 | 119.5 (2) | C17—C16—H16B | 109.5 |
C5—C4—H4 | 120.2 | C15—C16—H16A | 109.5 |
C18—C17—C16 | 127.2 (3) | C15—C16—H16B | 109.5 |
C18—C17—C22 | 115.7 (3) | H16A—C16—H16B | 108.1 |
C22—C17—C16 | 117.1 (3) | C21—C20—H20 | 120.0 |
C6—C1—H1 | 119.5 | C19—C20—H20 | 120.0 |
C2—C1—C6 | 120.9 (2) | C19—C20—C21 | 120.0 (3) |
C2—C1—H1 | 119.5 | C17—C22—H22 | 118.8 |
C6—C5—H5 | 120.0 | C21—C22—C17 | 122.4 (3) |
C4—C5—C6 | 119.9 (3) | C21—C22—H22 | 118.8 |
C4—C5—H5 | 120.0 | C20—C21—C22 | 119.9 (3) |
C17—C18—N2 | 121.9 (3) | C20—C21—H21 | 120.0 |
C17—C18—C19 | 122.4 (3) | C22—C21—H21 | 120.0 |
C19—C18—N2 | 115.7 (3) | C18—C19—H19 | 120.2 |
C14—C15—H15A | 108.9 | C20—C19—C18 | 119.6 (3) |
C14—C15—H15B | 108.9 | C20—C19—H19 | 120.2 |
C14—C15—C16 | 113.4 (2) | ||
Cl1—C9—C8—N1 | −1.0 (3) | C14—C15—C16—C17 | 170.5 (3) |
Cl1—C9—C8—C13 | 179.59 (17) | C4—C3—C2—C1 | −2.6 (4) |
Cl1—C9—C10—C11 | 178.5 (2) | C17—C18—N2—O4B | 36.3 (8) |
Cl2—C3—C4—C5 | −178.2 (2) | C17—C18—N2—O5A | 151.0 (9) |
Cl2—C3—C2—C1 | 178.4 (2) | C17—C18—N2—O4A | −13.5 (7) |
O2—N1—C8—C9 | 78.1 (2) | C17—C18—N2—O5B | −150.8 (4) |
O2—N1—C8—C13 | −102.5 (2) | C17—C18—C19—C20 | 0.2 (4) |
O2—N1—C7—O1 | 13.8 (3) | C17—C22—C21—C20 | −0.4 (5) |
O2—N1—C7—C6 | −168.96 (18) | C1—C6—C5—C4 | −1.8 (4) |
O2—C14—C15—C16 | −171.8 (2) | C5—C6—C1—C2 | 2.1 (4) |
O1—C7—C6—C1 | −34.9 (3) | C18—C17—C16—C15 | 89.3 (3) |
O1—C7—C6—C5 | 143.9 (3) | C18—C17—C22—C21 | 0.0 (4) |
O3—C14—C15—C16 | 5.3 (5) | N2—C18—C19—C20 | −178.5 (3) |
N1—O2—C14—O3 | 2.9 (4) | C12—C11—C10—C9 | 1.1 (4) |
N1—O2—C14—C15 | −179.87 (19) | C10—C9—C8—N1 | 176.6 (2) |
N1—C8—C13—C12 | −176.8 (2) | C10—C9—C8—C13 | −2.7 (3) |
N1—C7—C6—C1 | 147.9 (2) | C10—C11—C12—C13 | −1.2 (4) |
N1—C7—C6—C5 | −33.3 (3) | C2—C3—C4—C5 | 2.9 (4) |
C9—C8—C13—C12 | 2.6 (3) | C16—C17—C18—N2 | 0.9 (4) |
C8—N1—C7—O1 | 148.4 (2) | C16—C17—C18—C19 | −177.7 (2) |
C8—N1—C7—C6 | −34.3 (3) | C16—C17—C22—C21 | 178.1 (3) |
C8—C9—C10—C11 | 0.8 (4) | C22—C17—C18—N2 | 178.7 (3) |
C8—C13—C12—C11 | −0.7 (4) | C22—C17—C18—C19 | 0.1 (4) |
C7—N1—C8—C9 | −57.7 (3) | C22—C17—C16—C15 | −88.4 (3) |
C7—N1—C8—C13 | 121.7 (2) | C21—C20—C19—C18 | −0.5 (5) |
C7—C6—C1—C2 | −179.0 (2) | C19—C18—N2—O4B | −145.0 (8) |
C7—C6—C5—C4 | 179.4 (2) | C19—C18—N2—O5A | −30.3 (10) |
C6—C1—C2—C3 | 0.1 (4) | C19—C18—N2—O4A | 165.2 (6) |
C3—C4—C5—C6 | −0.6 (4) | C19—C18—N2—O5B | 27.9 (5) |
C14—O2—N1—C8 | 132.4 (2) | C19—C20—C21—C22 | 0.6 (5) |
C14—O2—N1—C7 | −86.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.93 | 2.52 | 3.354 (4) | 150 |
C13—H13···O3ii | 0.93 | 2.48 | 3.223 (4) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H16Cl2N2O5 |
Mr | 459.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.1574 (8), 10.1976 (6), 12.1736 (8) |
α, β, γ (°) | 91.847 (5), 108.327 (8), 100.285 (6) |
V (Å3) | 1057.06 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.32 × 0.28 × 0.25 |
Data collection | |
Diffractometer | Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.843, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7898, 4785, 3434 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.674 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.139, 1.04 |
No. of reflections | 4785 |
No. of parameters | 298 |
No. of restraints | 24 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.45 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.93 | 2.52 | 3.354 (4) | 150 |
C13—H13···O3ii | 0.93 | 2.48 | 3.223 (4) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z. |
Acknowledgements
This work was supported by the Natural Science Fund Projects of Gansu Province (0710RJZA124).
References
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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 (Noh et al., 2009; Zeng et al., 2003). We have performed the crystal structure determination of the title hydroxamic acid derivative.
The molecular structure of the title compound is shown in Fig. 1. The nitro-substituted benzene ring (C17-C22) forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the p-chloro (C1-C6) and o-chloro-substituted (C8-C13) benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 68.19 (13) °. Closely related structures appear in the literature (Zhang et al., 2012; Ma et al., 2012). In the crystal, weak C—H···O(═C) hydrogen bonds links molecules along [100] (Fig. 2).