organic compounds
N-(5-Chloro-2-hydroxyphenyl)-N′-(3-hydroxypropyl)oxalamide
aKey Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China
*Correspondence e-mail: wuzy@ouc.edu.cn
In the structure of the title N,N′-bis(substituted)oxamide compound, C11H13ClN2O4, the chlorohydroxyphenyl ring plane subtends an angle of 15.06 (13)° to the plane of the oxalamide unit. This in turn is inclined to the hydroxypropyl substituent by 78.03 (14)°. In the crystal, classical O—H⋯O and N—H⋯O hydrogen bonds give rise to a three-dimensional supramolecular structure.
Keywords: crystal structure; oxamide compounds; hydrogen bonds.
CCDC reference: 1446193
Structure description
Oxamide complexes are of considerable current interest due to their DNA-binding properties and cytotoxic activity (Martínez-Martínez et al., 1998; Li et al., 2012; Yue et al., 2012 and Zheng et al., 2012). The title oxamide compound, N-(5-chloro-2-hydroxyphenyl)-N′-(3-hydroxypropyl)oxalamide (H3chhpox), adopts a transoid conformation as expected (Fig. 1). The benzene ring substituent is almost coplanar with the oxamide group with a C7—N1—C1—C6 torsion angle of 11.8 (4)° while the other hydroxyphenyl substituent arm is almost orthogonal to this plane with a C8—N2—C9—C10 torsion angle of 92.4 (3)°.
In the crystal, layers are formed parallel to the ac plane through O—H⋯O hydrogen bonds (Fig. 2, Table 1). Inversion-related N—H⋯O hydrogen bonds between the oxamide groups connect the parallel layers into a three-dimensional supramolecular structure.
Synthesis and crystallization
The synthesis of the title compound (H3chhpox) was achieved in two steps. The first was the preparation of N-(5-chloro-2-hydroxyphenyl)oxalamide (H3chox) according to a reported method (Marmur, 1961). Next, H3chox (5 mmol, 1.22 g) in 20 mL absolute ethanol was added dropwise to 20 mL of an absolute ethanol solution containing 3-amino-1-propanol (6 mmol, 0.76 mL) at 273 K. The resulting solution was stirred for 2 h, and H3chhpox was precipitated as a white powder. It was then recrystallized from ethanol at 273 K and dried under vacuum. Well-shaped colorless single crystals were obtained by slow evaporation of an ethanol solution of the recrystallized product. Yield: 83%. Analysis calculated for C11H13N2O4Cl: C, 48.45; H, 4.81; N, 10.27%. Found: C, 48.96; H, 4.77; N, 10.65%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1446193
10.1107/S2414314616007379/sj4028sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616007379/sj4028Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616007379/sj4028Isup3.cml
The synthesis of the title compound (H3chhpox) was achieved in two steps. The first was the preparation of N-(5-chloro-2-hydroxyphenyl)oxalamide (H3chox) according to a reported method (Marmur, 1961). Next, H3chox (5mmol, 1.22g) in 20mL absolute ethanol was added dropwise to 20mL of an absolute ethanol solution containing (6mmol, 0.76mL) 3-amino-1-propanol at 273K. The resulting solution was stirred for 2h, and H3chhpox was precipitated as a white powder. It was then recrystallized from ethanol at 273K and dried under vacuum. Well-shaped colorless single crystals were obtained by slow evaporation of an ethanol solution of the recrystallized product. Yield: 83%. Anal. Calcd for C11H13N2O4Cl: C, 48.45; H, 4.81; N, 10.27%. Found: C, 48.96; H, 4.77; N, 10.65%.
The synthesis of the title compound (H3chhpox) was achieved in two steps. The first was the preparation of N-(5-chloro-2-hydroxyphenyl)oxalamide (H3chox) according to a reported method (Marmur, 1961). Next, H3chox (5 mmol, 1.22 g) in 20 mL absolute ethanol was added dropwise to 20 mL of an absolute ethanol solution containing 3-amino-1-propanol (6 mmol, 0.76 mL) at 273 K. The resulting solution was stirred for 2 h, and H3chhpox was precipitated as a white powder. It was then recrystallized from ethanol at 273 K and dried under vacuum. Well-shaped colorless single crystals were obtained by slow evaporation of an ethanol solution of the recrystallized product. Yield: 83%. Anal. Calcd for C11H13N2O4Cl: C, 48.45; H, 4.81; N, 10.27%. Found: C, 48.96; H, 4.77; N, 10.65%.
Oxamide complexes are of considerable current interest due to their DNA-binding properties and cytotoxic activity (Martínez-Martínez et al., 1998; Li et al., 2012; Yue et al., 2012 and Zheng et al., 2012). The title oxamide compound, N-(5-chloro-2-hydroxyphenyl)-N'-(3-hydroxypropyl)oxalamide (H3chhpox), adopts a
conformation as expected (Fig. 1). The benzene ring substituent is almost coplanar with the oxamide group with a C7—N1—C1—C6 torsion angle of 11.8 (4)° while the other hydroxyphenyl substituent arm is almost orthogonal to this plane with a C8—N2—C9—C10 torsion angle of 92.4 (3)°.In the crystal, layers are formed parallel to the ac plane through O—H···O hydrogen bonds (Fig. 2, Table 1). Inversion-related N—H···O hydrogen bonds between the oxamide groups connect the parallel layers into a three-dimensional supramolecular structure.
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. A two-dimensional hydrogen-bonding network parallel to (010), constructed by classical O—H···O interactions. [Symmetry codes: (i) x - 3/2, 3/2 - y, z + 1/2; (ii) x + 1, y, z; (iii) x + 3/2, 3/2 - y, z - 1/2; (iv) x - 1, y, z.] |
C11H13ClN2O4 | F(000) = 568 |
Mr = 272.68 | Dx = 1.490 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1422 (14) Å | Cell parameters from 2400 reflections |
b = 18.117 (4) Å | θ = 3.5–25.0° |
c = 11.061 (2) Å | µ = 0.32 mm−1 |
β = 98.896 (8)° | T = 296 K |
V = 1216.0 (5) Å3 | Prism, colorless |
Z = 4 | 0.49 × 0.16 × 0.03 mm |
Bruker APEX area-detector diffractometer | 1672 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
φ and ω scans | θmax = 27.5°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −7→7 |
Tmin = 0.697, Tmax = 0.746 | k = −23→23 |
10616 measured reflections | l = −13→14 |
2779 independent reflections |
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)] = 0.047 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.107 | All H-atom parameters refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0419P)2 + 0.2977P] where P = (Fo2 + 2Fc2)/3 |
2779 reflections | (Δ/σ)max < 0.001 |
215 parameters | Δρmax = 0.25 e Å−3 |
2 restraints | Δρmin = −0.20 e Å−3 |
C11H13ClN2O4 | V = 1216.0 (5) Å3 |
Mr = 272.68 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.1422 (14) Å | µ = 0.32 mm−1 |
b = 18.117 (4) Å | T = 296 K |
c = 11.061 (2) Å | 0.49 × 0.16 × 0.03 mm |
β = 98.896 (8)° |
Bruker APEX area-detector diffractometer | 2779 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1672 reflections with I > 2σ(I) |
Tmin = 0.697, Tmax = 0.746 | Rint = 0.054 |
10616 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 2 restraints |
wR(F2) = 0.107 | All H-atom parameters refined |
S = 1.00 | Δρmax = 0.25 e Å−3 |
2779 reflections | Δρmin = −0.20 e Å−3 |
215 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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 | ||
Cl1 | 0.54932 (13) | 0.33941 (3) | 0.39890 (7) | 0.0621 (3) | |
O1 | 0.2065 (3) | 0.63169 (9) | 0.24549 (16) | 0.0484 (5) | |
O2 | 0.7936 (3) | 0.50435 (8) | 0.08106 (16) | 0.0485 (5) | |
O3 | 0.6905 (2) | 0.69246 (8) | 0.03286 (14) | 0.0400 (4) | |
O4 | 1.4561 (3) | 0.80399 (10) | −0.10518 (19) | 0.0523 (5) | |
N1 | 0.5547 (3) | 0.58139 (10) | 0.15803 (17) | 0.0334 (5) | |
N2 | 0.8959 (3) | 0.61585 (10) | −0.06633 (18) | 0.0356 (5) | |
C1 | 0.4604 (3) | 0.53575 (11) | 0.23849 (19) | 0.0312 (5) | |
C2 | 0.2779 (4) | 0.56333 (12) | 0.2848 (2) | 0.0356 (5) | |
C3 | 0.1802 (4) | 0.52106 (14) | 0.3647 (2) | 0.0449 (6) | |
C4 | 0.2617 (4) | 0.45182 (13) | 0.4005 (2) | 0.0450 (6) | |
C5 | 0.4420 (4) | 0.42605 (12) | 0.3552 (2) | 0.0390 (6) | |
C6 | 0.5429 (4) | 0.46656 (12) | 0.2747 (2) | 0.0345 (5) | |
C7 | 0.7077 (3) | 0.56439 (11) | 0.0884 (2) | 0.0310 (5) | |
C8 | 0.7663 (3) | 0.63118 (11) | 0.0148 (2) | 0.0308 (5) | |
C9 | 0.9727 (4) | 0.67265 (14) | −0.1426 (2) | 0.0385 (6) | |
C10 | 1.1919 (4) | 0.70438 (13) | −0.0862 (2) | 0.0363 (6) | |
C11 | 1.2472 (4) | 0.77284 (13) | −0.1527 (2) | 0.0398 (6) | |
H1 | 0.507 (4) | 0.6260 (14) | 0.150 (2) | 0.049 (7)* | |
H1A | 0.122 (4) | 0.6487 (14) | 0.288 (2) | 0.061 (9)* | |
H2 | 0.946 (4) | 0.5705 (14) | −0.068 (2) | 0.052 (8)* | |
H3 | 0.060 (4) | 0.5401 (13) | 0.394 (2) | 0.048 (7)* | |
H4 | 0.191 (4) | 0.4237 (12) | 0.453 (2) | 0.044 (7)* | |
H4A | 1.527 (5) | 0.7724 (14) | −0.065 (3) | 0.086 (12)* | |
H6 | 0.663 (4) | 0.4498 (12) | 0.2439 (19) | 0.038 (6)* | |
H9A | 0.863 (4) | 0.7103 (13) | −0.158 (2) | 0.048 (7)* | |
H9B | 0.985 (4) | 0.6512 (13) | −0.223 (2) | 0.051 (7)* | |
H10A | 1.300 (4) | 0.6690 (13) | −0.089 (2) | 0.049 (7)* | |
H10B | 1.191 (4) | 0.7173 (12) | 0.001 (2) | 0.047 (7)* | |
H11A | 1.134 (4) | 0.8107 (13) | −0.142 (2) | 0.051 (7)* | |
H11B | 1.244 (4) | 0.7627 (13) | −0.239 (2) | 0.055 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0836 (6) | 0.0395 (4) | 0.0696 (5) | 0.0142 (3) | 0.0319 (4) | 0.0192 (3) |
O1 | 0.0533 (12) | 0.0387 (9) | 0.0596 (12) | 0.0148 (8) | 0.0290 (10) | 0.0017 (8) |
O2 | 0.0544 (11) | 0.0292 (9) | 0.0709 (12) | 0.0096 (8) | 0.0384 (10) | 0.0073 (8) |
O3 | 0.0459 (10) | 0.0263 (8) | 0.0499 (10) | 0.0023 (7) | 0.0141 (8) | 0.0018 (7) |
O4 | 0.0427 (11) | 0.0400 (10) | 0.0750 (14) | −0.0110 (9) | 0.0117 (10) | 0.0195 (10) |
N1 | 0.0382 (11) | 0.0235 (10) | 0.0425 (12) | 0.0032 (8) | 0.0186 (9) | 0.0008 (8) |
N2 | 0.0357 (11) | 0.0289 (10) | 0.0461 (12) | −0.0019 (9) | 0.0184 (10) | 0.0019 (9) |
C1 | 0.0342 (12) | 0.0274 (11) | 0.0339 (12) | −0.0022 (9) | 0.0108 (10) | −0.0037 (9) |
C2 | 0.0374 (13) | 0.0289 (11) | 0.0425 (14) | 0.0035 (10) | 0.0127 (11) | −0.0046 (10) |
C3 | 0.0439 (15) | 0.0473 (15) | 0.0495 (16) | 0.0031 (12) | 0.0257 (13) | −0.0036 (12) |
C4 | 0.0556 (17) | 0.0402 (14) | 0.0447 (15) | −0.0047 (12) | 0.0253 (13) | 0.0021 (12) |
C5 | 0.0497 (15) | 0.0310 (12) | 0.0383 (14) | 0.0001 (11) | 0.0129 (12) | −0.0003 (10) |
C6 | 0.0364 (14) | 0.0310 (12) | 0.0393 (13) | 0.0033 (10) | 0.0154 (11) | −0.0009 (10) |
C7 | 0.0307 (12) | 0.0257 (11) | 0.0383 (13) | −0.0012 (10) | 0.0105 (10) | −0.0026 (10) |
C8 | 0.0272 (12) | 0.0285 (11) | 0.0366 (13) | −0.0026 (9) | 0.0050 (10) | −0.0007 (10) |
C9 | 0.0384 (15) | 0.0399 (14) | 0.0395 (15) | −0.0035 (12) | 0.0129 (12) | 0.0060 (12) |
C10 | 0.0351 (14) | 0.0324 (12) | 0.0430 (15) | −0.0028 (11) | 0.0105 (11) | 0.0063 (11) |
C11 | 0.0433 (15) | 0.0352 (13) | 0.0429 (16) | −0.0037 (12) | 0.0131 (12) | 0.0075 (12) |
Cl1—C5 | 1.742 (2) | C3—C4 | 1.385 (3) |
O1—C2 | 1.362 (3) | C3—H3 | 0.92 (2) |
O1—H1A | 0.813 (17) | C4—C5 | 1.366 (3) |
O2—C7 | 1.217 (2) | C4—H4 | 0.93 (2) |
O3—C8 | 1.232 (2) | C5—C6 | 1.374 (3) |
O4—C11 | 1.426 (3) | C6—H6 | 0.91 (2) |
O4—H4A | 0.812 (17) | C7—C8 | 1.532 (3) |
N1—C7 | 1.340 (3) | C9—C10 | 1.507 (3) |
N1—C1 | 1.404 (3) | C9—H9A | 0.96 (2) |
N1—H1 | 0.86 (2) | C9—H9B | 0.98 (2) |
N2—C8 | 1.317 (3) | C10—C11 | 1.507 (3) |
N2—C9 | 1.454 (3) | C10—H10A | 0.93 (2) |
N2—H2 | 0.88 (2) | C10—H10B | 0.99 (2) |
C1—C6 | 1.388 (3) | C11—H11A | 1.00 (2) |
C1—C2 | 1.395 (3) | C11—H11B | 0.97 (2) |
C2—C3 | 1.375 (3) | ||
C2—O1—H1A | 111.1 (19) | C1—C6—H6 | 118.3 (14) |
C11—O4—H4A | 107 (2) | O2—C7—N1 | 126.43 (19) |
C7—N1—C1 | 128.59 (18) | O2—C7—C8 | 122.01 (18) |
C7—N1—H1 | 114.1 (16) | N1—C7—C8 | 111.56 (17) |
C1—N1—H1 | 117.2 (16) | O3—C8—N2 | 125.7 (2) |
C8—N2—C9 | 122.0 (2) | O3—C8—C7 | 119.94 (18) |
C8—N2—H2 | 117.3 (16) | N2—C8—C7 | 114.32 (18) |
C9—N2—H2 | 120.4 (16) | N2—C9—C10 | 112.3 (2) |
C6—C1—C2 | 119.7 (2) | N2—C9—H9A | 109.1 (14) |
C6—C1—N1 | 123.15 (19) | C10—C9—H9A | 111.4 (14) |
C2—C1—N1 | 117.09 (18) | N2—C9—H9B | 108.7 (14) |
O1—C2—C3 | 124.1 (2) | C10—C9—H9B | 109.7 (14) |
O1—C2—C1 | 116.49 (19) | H9A—C9—H9B | 106 (2) |
C3—C2—C1 | 119.4 (2) | C11—C10—C9 | 111.5 (2) |
C2—C3—C4 | 120.9 (2) | C11—C10—H10A | 109.9 (14) |
C2—C3—H3 | 118.0 (15) | C9—C10—H10A | 108.7 (14) |
C4—C3—H3 | 121.1 (15) | C11—C10—H10B | 108.4 (13) |
C5—C4—C3 | 118.8 (2) | C9—C10—H10B | 110.5 (13) |
C5—C4—H4 | 121.6 (14) | H10A—C10—H10B | 108 (2) |
C3—C4—H4 | 119.6 (14) | O4—C11—C10 | 113.8 (2) |
C4—C5—C6 | 121.9 (2) | O4—C11—H11A | 106.9 (13) |
C4—C5—Cl1 | 119.99 (18) | C10—C11—H11A | 107.2 (13) |
C6—C5—Cl1 | 118.14 (17) | O4—C11—H11B | 108.6 (14) |
C5—C6—C1 | 119.2 (2) | C10—C11—H11B | 110.7 (15) |
C5—C6—H6 | 122.5 (14) | H11A—C11—H11B | 109.4 (19) |
C7—N1—C1—C6 | 11.8 (4) | C2—C1—C6—C5 | 0.5 (3) |
C7—N1—C1—C2 | −169.5 (2) | N1—C1—C6—C5 | 179.1 (2) |
C6—C1—C2—O1 | 179.8 (2) | C1—N1—C7—O2 | 0.9 (4) |
N1—C1—C2—O1 | 1.1 (3) | C1—N1—C7—C8 | −179.4 (2) |
C6—C1—C2—C3 | −0.9 (3) | C9—N2—C8—O3 | 2.5 (4) |
N1—C1—C2—C3 | −179.5 (2) | C9—N2—C8—C7 | −178.6 (2) |
O1—C2—C3—C4 | 179.9 (2) | O2—C7—C8—O3 | −173.5 (2) |
C1—C2—C3—C4 | 0.5 (4) | N1—C7—C8—O3 | 6.7 (3) |
C2—C3—C4—C5 | 0.2 (4) | O2—C7—C8—N2 | 7.5 (3) |
C3—C4—C5—C6 | −0.6 (4) | N1—C7—C8—N2 | −172.22 (19) |
C3—C4—C5—Cl1 | 179.7 (2) | C8—N2—C9—C10 | 92.4 (3) |
C4—C5—C6—C1 | 0.3 (4) | N2—C9—C10—C11 | −168.6 (2) |
Cl1—C5—C6—C1 | 179.97 (18) | C9—C10—C11—O4 | −178.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O4i | 0.81 (2) | 1.88 (2) | 2.690 (2) | 173 (3) |
O4—H4A···O3ii | 0.81 (2) | 1.98 (2) | 2.794 (2) | 178 (3) |
N2—H2···O2iii | 0.88 (2) | 2.12 (3) | 2.916 (2) | 150 (2) |
Symmetry codes: (i) x−3/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O4i | 0.813 (17) | 1.881 (17) | 2.690 (2) | 173 (3) |
O4—H4A···O3ii | 0.812 (17) | 1.983 (18) | 2.794 (2) | 178 (3) |
N2—H2···O2iii | 0.88 (2) | 2.12 (3) | 2.916 (2) | 150 (2) |
Symmetry codes: (i) x−3/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C11H13ClN2O4 |
Mr | 272.68 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 6.1422 (14), 18.117 (4), 11.061 (2) |
β (°) | 98.896 (8) |
V (Å3) | 1216.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.49 × 0.16 × 0.03 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.697, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10616, 2779, 1672 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.107, 1.00 |
No. of reflections | 2779 |
No. of parameters | 215 |
No. of restraints | 2 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.25, −0.20 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), XP in SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 2012).
Acknowledgements
This project was supported by the National Natural Science Foundation of China (Nos. 51273184 and 81202399) and the Open Research Fund Program of the Key Laboratory of Marine Drugs (Ocean University of China), Ministry of Education [No. KLMD(OUC) 201401].
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