N-(5-Chloro-2-hy­droxy­phen­yl)-N′-(3-hy­droxy­prop­yl)oxalamide

Wang, C.-K.; Zheng, K.; Li, Y.-T.; Wu, Z.-Y.

doi:10.1107/S2414314616007379

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160737

doi:10.1107/S2414314616007379

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N-(5-Chloro-2-hydroxyphenyl)-N′-(3-hydroxypropyl)oxalamide

Chang-Kai Wang,^a Kang Zheng,^a Yan-Tuan Li ^a and Zhi-Yong Wu ^a ^*

^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

Edited by J. Simpson, University of Otago, New Zealand (Received 25 April 2016; accepted 3 May 2016; online 6 May 2016)

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

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Chemical scheme

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)°.

Figure 1
The molecular structure with displacement ellipsoids drawn at the 30% probability level.

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.

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x+2, -y+1, -z.

Figure 2
The two-dimensional hydrogen-bonding network parallel to (010), constructed by classical O—H⋯O interactions. [Symmetry codes: (i) x − $[{3\over 2}]$ , $[{3\over 2}]$ − y, z + $[{1\over 2}]$ ; (ii) x + 1, y, z; (iii) x + $[{3\over 2}]$ , $[{3\over 2}]$ − y, z − $[{1\over 2}]$ ; (iv) x − 1, y, z.]

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₁₃ClN₂O₄
M_r	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 )
T_min, T_max	0.697, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10616, 2779, 1672
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20
Computer programs: SMART and SAINT (Bruker, 2002), SHELXS97 and XP in SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), and WinGX (Farrugia, 2012 ).

Structural data

CCDC reference: 1446193

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616007379/sj4028sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007379/sj4028Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616007379/sj4028Isup3.cml

checkCIF report

Synthesis and crystallization top

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%.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1

Experimental top

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%.

Structure description top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

Figures top

	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.]

N-(5-Chloro-2-hydroxyphenyl)-N'-(3-hydroxypropyl)ethanediamide top

Crystal data top

C₁₁H₁₃ClN₂O₄	F(000) = 568
M_r = 272.68	D_x = 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

Data collection top

Bruker APEX area-detector diffractometer	1672 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
φ and ω scans	θ_max = 27.5°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
T_min = 0.697, T_max = 0.746	k = −23→23
10616 measured reflections	l = −13→14
2779 independent reflections

Refinement top

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(F_o²) + (0.0419P)² + 0.2977P] where P = (F_o² + 2F_c²)/3
2779 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₁H₁₃ClN₂O₄	V = 1216.0 (5) Å³
M_r = 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)°

Data collection top

Bruker APEX area-detector diffractometer	2779 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1672 reflections with I > 2σ(I)
T_min = 0.697, T_max = 0.746	R_int = 0.054
10616 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.107	All H-atom parameters refined
S = 1.00	Δρ_max = 0.25 e Å⁻³
2779 reflections	Δρ_min = −0.20 e Å⁻³
215 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.697, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10616, 2779, 1672
R_int	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
Δρ_max, Δρ_min (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].

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Li, X.-W., Tao, L., Li, Y.-T., Wu, Z.-Y. & Yan, C.-W. (2012). Eur. J. Med. Chem. 54, 697–708. Web of Science CSD CrossRef CAS PubMed Google Scholar
Marmur, J. (1961). J. Mol. Biol. 3, 208–218. CrossRef CAS Google Scholar
Martínez-Martínez, F. J., Padilla-Martínez, I. I., Brito, M. A., Geniz, E. D., Rojas, R. C., Saavedra, J. B. R., Höpfl, H., Tlahuextl, M. & Contreras, R. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 401–406. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Yue, X.-T., Li, X.-W. & Wu, Z.-Y. (2012). Acta Cryst. E68, o8. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Y.-J., Zheng, K., Wu, Z.-Y. & Li, Y. (2012). Acta Cryst. E68, o895. CSD CrossRef IUCr Journals Google Scholar

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Volume 1| Part 5| May 2016| x160737

doi:10.1107/S2414314616007379

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(5-Chloro-2-hy­dr­oxy­phen­yl)-N′-(3-hy­dr­oxy­prop­yl)oxalamide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

N-(5-Chloro-2-hydroxyphenyl)-N′-(3-hydroxypropyl)oxalamide