(2R,3R)-N-(4-Chloro­phen­yl)-2,3-dihydr­oxy-N′-(5-phenyl-1,3,4-thia­diazol-2-yl)succinamide

Huang, H.-M.; Chen, G.-L.; Li, M.; Tu, G.-G.; Liu, C.-M.

doi:10.1107/S1600536810007919

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o765

doi:10.1107/S1600536810007919

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(2R,3R)-N-(4-Chlorophenyl)-2,3-dihydroxy-N′-(5-phenyl-1,3,4-thiadiazol-2-yl)succinamide

Hui-Ming Huang,^a,^b Gen-Lin Chen,^b ^* Min Li,^b Guo-Gang Tu ^b and Cheng-Mei Liu ^a

^aState Key Laboratory of Food Science and Technology, Nanchang University, 330047 Nanchang, Jiangxi, People's Republic of China, and ^bNanchang University School of Pharmaceutical Science, 330006 Nanchang, Jiangxi, People's Republic of China
^*Correspondence e-mail: huiminghuang@yahoo.cn

(Received 8 February 2010; accepted 2 March 2010; online 6 March 2010)

In the structure of the title compound, C₁₈H₁₅ClN₄O₄S, the dihedral angle between the two benzene rings is 1.4 (3)°. The angle between the phenyl ring and thiadiazole ring is 5.8 (4)°. The conformations of the N—H and C=O bonds are anti with respect to each other. In the crystal structure, molecules are linked by intermolecular O—H⋯N, N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis, see: Marson & Melling (2005 ); Tu et al. (2008 ); Shriner & Furrow (1955 ). For related structures, see: Watadani et al. (2005 ); Li et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₅ClN₄O₄S
M_r = 418.85
Monoclinic, C 2
a = 41.381 (3) Å
b = 5.1744 (5) Å
c = 8.7442 (9) Å
β = 98.315 (1)°
V = 1852.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 K
0.46 × 0.40 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.855, T_max = 0.962
4632 measured reflections
2697 independent reflections
2319 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.091
S = 1.04
2697 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ), 863 Friedel pairs
Flack parameter: 0.03 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1ⁱ	0.82	1.95	2.733 (3)	159
N3—H3B⋯O3ⁱⁱ	0.86	2.35	3.061 (4)	140
O4—H4⋯O1ⁱⁱⁱ	0.82	2.02	2.790 (3)	155
N4—H4A⋯O2^iv	0.86	2.17	2.951 (4)	151
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+2]$ ; (iv) x, y+1, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007919/im2182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007919/im2182Isup2.hkl

checkCIF report

Comment top

The present tartaric acid derivate is in continuation to our previously reported crystal structure of thiadiazole scaffold compounds (Li et al., 2008). The title compound (Fig. 1) was synthesized according to literature procedures (Marson & Melling 2005; Tu et al., 2008; Shriner & Furrow 1995) and crystallized in the monoclinic crystal system. The dihedral angle between the two benzene rings is 1.4 (3)°; the angle between the benzene ring (C7-C12) and thiadiazole ring is 5.8 (4)°. The conformations of the N—H and C=O bonds are anti with respect to each other. Bond lengths and angles are in normal ranges and comparable to those in related structures (Watadani et al., 2005). In the crystal structure, molecules are linked by intermolecular O—H···N, N—H···O and O—H···O hydrogen bonds forming a three-dimensional network (Table 1, Figure 2).

Related literature top

For the synthesic procedure, see: Marson & Melling (2005); Tu et al. (2008); Shriner & Furrow (1955). For related structures, see: Watadani et al. (2005); Li et al. (2008).

Experimental top

To a solution of 2-amino-5-phenyl-1,3,4-thiadiazole (10 mmol) in THF was added diacetyl-L-tartaric anhydride (12 mmol). After the mixture was stirred at room temperature for 16 h, N,N-dicyclohexylcarbodiimide (9 mmol) and p-chloroaniline (9 mmol) in THF were added to the mixture. The reaction mixture was stirred at room temperature overnight. After insoluble material was filtered off the filtrate was evaporated in vacuo. The residual was hydrolyzed by a solution of K₂CO₃ in methanol at 65°C for 2 h and recrystallized from THF to afford the target compound. Yield: 3.06 g, 81%, m.p. 221-222°C. Colorless block-shaped single crystals of the title compound suitable for X-ray diffraction analysis precipitated after several days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of title compound, viewed along the b axis with hydrogen bonds drawn as dashed lines.

(2R,3R)-N-(4-Chlorophenyl)-2,3-dihydroxy-N'-(5- phenyl-1,3,4-thiadiazol-2-yl)succinamide top

Crystal data top

C₁₈H₁₅ClN₄O₄S	F(000) = 864
M_r = 418.85	D_x = 1.502 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2277 reflections
a = 41.381 (3) Å	θ = 2.4–27.9°
b = 5.1744 (5) Å	µ = 0.35 mm⁻¹
c = 8.7442 (9) Å	T = 298 K
β = 98.315 (1)°	Block, colourless
V = 1852.6 (3) Å³	0.46 × 0.40 × 0.11 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2697 independent reflections
Radiation source: fine-focus sealed tube	2319 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −44→48
T_min = 0.855, T_max = 0.962	k = −6→4
4632 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0471P)² + 0.5765P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2697 reflections	Δρ_max = 0.19 e Å⁻³
253 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 863 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (8)

Crystal data top

C₁₈H₁₅ClN₄O₄S	V = 1852.6 (3) Å³
M_r = 418.85	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 41.381 (3) Å	µ = 0.35 mm⁻¹
b = 5.1744 (5) Å	T = 298 K
c = 8.7442 (9) Å	0.46 × 0.40 × 0.11 mm
β = 98.315 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2697 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2319 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.962	R_int = 0.022
4632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.19 e Å⁻³
S = 1.04	Δρ_min = −0.15 e Å⁻³
2697 reflections	Absolute structure: Flack (1983), 863 Friedel pairs
253 parameters	Absolute structure parameter: 0.03 (8)
1 restraint

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 > 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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.51651 (2)	0.5674 (3)	0.31490 (11)	0.0776 (4)
N1	0.82422 (6)	0.6761 (7)	0.6878 (3)	0.0533 (8)
N2	0.85606 (6)	0.7102 (6)	0.7553 (3)	0.0510 (8)
N3	0.77780 (5)	0.4311 (5)	0.7013 (3)	0.0438 (7)
H3B	0.7686	0.5112	0.6203	0.053*
N4	0.64966 (5)	0.5279 (6)	0.6689 (3)	0.0412 (6)
H4A	0.6589	0.6749	0.6906	0.049*
O1	0.76958 (5)	0.1304 (5)	0.8778 (3)	0.0567 (7)
O2	0.65669 (5)	0.0938 (5)	0.7001 (3)	0.0587 (6)
O3	0.72236 (4)	0.3604 (6)	0.5396 (2)	0.0508 (6)
H3	0.7052	0.3206	0.4860	0.076*
O4	0.70977 (5)	0.6252 (4)	0.8040 (2)	0.0485 (6)
H4	0.7120	0.6645	0.8958	0.073*
S1	0.833503 (16)	0.34609 (19)	0.90607 (8)	0.0471 (2)
C1	0.75941 (7)	0.2576 (6)	0.7638 (3)	0.0394 (8)
C2	0.72451 (6)	0.2352 (7)	0.6839 (3)	0.0404 (8)
H2	0.7187	0.0524	0.6681	0.048*
C3	0.70219 (6)	0.3600 (7)	0.7875 (3)	0.0378 (6)
H3A	0.7059	0.2776	0.8894	0.045*
C4	0.66679 (6)	0.3166 (7)	0.7157 (3)	0.0386 (7)
C5	0.80992 (7)	0.4943 (7)	0.7539 (3)	0.0412 (8)
C6	0.86447 (6)	0.5530 (7)	0.8697 (3)	0.0374 (7)
C7	0.89748 (6)	0.5497 (7)	0.9587 (3)	0.0363 (7)
C8	0.92006 (7)	0.7319 (7)	0.9290 (4)	0.0510 (9)
H8	0.9142	0.8595	0.8553	0.061*
C9	0.95150 (8)	0.7257 (8)	1.0084 (4)	0.0590 (10)
H9	0.9667	0.8478	0.9869	0.071*
C10	0.96029 (7)	0.5415 (8)	1.1180 (4)	0.0557 (9)
H10	0.9814	0.5391	1.1716	0.067*
C11	0.93800 (7)	0.3592 (9)	1.1492 (4)	0.0558 (9)
H11	0.9441	0.2335	1.2238	0.067*
C12	0.90653 (7)	0.3624 (8)	1.0698 (3)	0.0469 (8)
H12	0.8915	0.2389	1.0911	0.056*
C13	0.61733 (6)	0.5301 (7)	0.5857 (3)	0.0373 (7)
C14	0.60929 (7)	0.7228 (7)	0.4779 (3)	0.0464 (8)
H14	0.6250	0.8437	0.4602	0.056*
C15	0.57817 (8)	0.7379 (7)	0.3959 (4)	0.0505 (9)
H15	0.5727	0.8704	0.3251	0.061*
C16	0.55547 (7)	0.5544 (7)	0.4205 (3)	0.0465 (8)
C17	0.56310 (6)	0.3612 (8)	0.5266 (4)	0.0505 (8)
H17	0.5475	0.2388	0.5428	0.061*
C18	0.59436 (6)	0.3490 (8)	0.6101 (3)	0.0455 (7)
H18	0.5997	0.2183	0.6824	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0454 (5)	0.1052 (10)	0.0745 (6)	0.0098 (6)	−0.0174 (4)	−0.0027 (6)
N1	0.0330 (13)	0.072 (2)	0.0507 (15)	−0.0065 (14)	−0.0070 (11)	0.0187 (15)
N2	0.0342 (13)	0.067 (2)	0.0487 (15)	−0.0096 (14)	−0.0045 (11)	0.0138 (15)
N3	0.0319 (12)	0.057 (2)	0.0389 (13)	−0.0026 (12)	−0.0077 (10)	0.0075 (12)
N4	0.0353 (12)	0.0280 (14)	0.0570 (14)	−0.0032 (12)	−0.0039 (10)	−0.0028 (13)
O1	0.0445 (11)	0.0624 (18)	0.0572 (13)	−0.0051 (12)	−0.0125 (10)	0.0186 (13)
O2	0.0386 (11)	0.0314 (14)	0.1006 (18)	−0.0036 (11)	−0.0086 (11)	0.0009 (13)
O3	0.0376 (10)	0.0773 (17)	0.0334 (10)	−0.0068 (13)	−0.0091 (8)	−0.0006 (12)
O4	0.0474 (12)	0.0397 (14)	0.0545 (12)	−0.0058 (11)	−0.0056 (9)	−0.0140 (10)
S1	0.0327 (3)	0.0557 (6)	0.0486 (4)	−0.0064 (4)	−0.0085 (3)	0.0129 (4)
C1	0.0365 (15)	0.043 (2)	0.0369 (15)	0.0019 (14)	−0.0022 (13)	−0.0028 (14)
C2	0.0332 (15)	0.042 (2)	0.0422 (16)	−0.0023 (14)	−0.0063 (12)	−0.0065 (15)
C3	0.0371 (14)	0.0351 (17)	0.0385 (14)	−0.0033 (16)	−0.0036 (11)	0.0013 (16)
C4	0.0350 (14)	0.0327 (19)	0.0469 (15)	−0.0010 (15)	0.0023 (12)	−0.0036 (15)
C5	0.0333 (14)	0.053 (2)	0.0356 (14)	0.0019 (15)	−0.0020 (12)	0.0008 (15)
C6	0.0333 (14)	0.043 (2)	0.0347 (14)	0.0013 (15)	0.0020 (11)	−0.0008 (15)
C7	0.0284 (13)	0.042 (2)	0.0374 (14)	−0.0007 (14)	0.0016 (11)	−0.0050 (15)
C8	0.0420 (17)	0.055 (2)	0.0530 (19)	−0.0029 (17)	−0.0049 (14)	0.0103 (17)
C9	0.0375 (17)	0.066 (3)	0.071 (2)	−0.0122 (17)	−0.0017 (16)	0.007 (2)
C10	0.0316 (15)	0.062 (3)	0.068 (2)	0.0018 (18)	−0.0092 (14)	0.000 (2)
C11	0.0433 (16)	0.061 (2)	0.0585 (19)	0.007 (2)	−0.0093 (14)	0.012 (2)
C12	0.0386 (14)	0.048 (2)	0.0519 (17)	−0.0052 (18)	−0.0012 (13)	0.0067 (19)
C13	0.0312 (13)	0.0354 (18)	0.0439 (15)	0.0022 (14)	0.0011 (11)	−0.0047 (15)
C14	0.0459 (17)	0.040 (2)	0.0516 (18)	−0.0033 (15)	0.0001 (14)	0.0037 (16)
C15	0.0555 (19)	0.046 (2)	0.0463 (17)	0.0077 (17)	−0.0040 (15)	0.0056 (16)
C16	0.0377 (15)	0.053 (2)	0.0461 (16)	0.0080 (18)	−0.0027 (13)	−0.0106 (17)
C17	0.0324 (14)	0.047 (2)	0.071 (2)	−0.0044 (18)	0.0031 (14)	−0.001 (2)
C18	0.0354 (14)	0.0396 (19)	0.0599 (18)	0.0019 (17)	0.0014 (13)	0.0069 (19)

Geometric parameters (Å, º) top

Cl1—C16	1.739 (3)	C6—C7	1.471 (3)
N1—C5	1.292 (4)	C7—C8	1.379 (4)
N1—N2	1.375 (3)	C7—C12	1.385 (5)
N2—C6	1.297 (4)	C8—C9	1.384 (4)
N3—C1	1.343 (4)	C8—H8	0.9300
N3—C5	1.381 (3)	C9—C10	1.363 (5)
N3—H3B	0.8600	C9—H9	0.9300
N4—C4	1.335 (4)	C10—C11	1.374 (5)
N4—C13	1.427 (3)	C10—H10	0.9300
N4—H4A	0.8600	C11—C12	1.384 (4)
O1—C1	1.218 (3)	C11—H11	0.9300
O2—C4	1.227 (4)	C12—H12	0.9300
O3—C2	1.410 (4)	C13—C18	1.373 (4)
O3—H3	0.8200	C13—C14	1.380 (5)
O4—C3	1.411 (4)	C14—C15	1.383 (4)
O4—H4	0.8200	C14—H14	0.9300
S1—C5	1.713 (3)	C15—C16	1.374 (5)
S1—C6	1.734 (3)	C15—H15	0.9300
C1—C2	1.515 (4)	C16—C17	1.369 (5)
C2—C3	1.528 (4)	C17—C18	1.392 (4)
C2—H2	0.9800	C17—H17	0.9300
C3—C4	1.525 (3)	C18—H18	0.9300
C3—H3A	0.9800

C5—N1—N2	112.0 (2)	C8—C7—C6	119.7 (3)
C6—N2—N1	112.6 (3)	C12—C7—C6	121.0 (3)
C1—N3—C5	126.7 (2)	C7—C8—C9	120.2 (3)
C1—N3—H3B	116.7	C7—C8—H8	119.9
C5—N3—H3B	116.7	C9—C8—H8	119.9
C4—N4—C13	125.5 (3)	C10—C9—C8	120.3 (3)
C4—N4—H4A	117.3	C10—C9—H9	119.8
C13—N4—H4A	117.3	C8—C9—H9	119.8
C2—O3—H3	109.5	C9—C10—C11	120.1 (3)
C3—O4—H4	109.5	C9—C10—H10	120.0
C5—S1—C6	86.24 (14)	C11—C10—H10	120.0
O1—C1—N3	123.0 (3)	C10—C11—C12	120.1 (3)
O1—C1—C2	122.0 (3)	C10—C11—H11	119.9
N3—C1—C2	115.0 (2)	C12—C11—H11	119.9
O3—C2—C1	108.1 (2)	C11—C12—C7	120.0 (3)
O3—C2—C3	111.8 (3)	C11—C12—H12	120.0
C1—C2—C3	108.2 (2)	C7—C12—H12	120.0
O3—C2—H2	109.6	C18—C13—C14	119.7 (3)
C1—C2—H2	109.6	C18—C13—N4	122.3 (3)
C3—C2—H2	109.6	C14—C13—N4	118.0 (3)
O4—C3—C4	111.8 (3)	C13—C14—C15	120.6 (3)
O4—C3—C2	109.1 (2)	C13—C14—H14	119.7
C4—C3—C2	108.7 (2)	C15—C14—H14	119.7
O4—C3—H3A	109.0	C16—C15—C14	119.1 (3)
C4—C3—H3A	109.0	C16—C15—H15	120.4
C2—C3—H3A	109.0	C14—C15—H15	120.4
O2—C4—N4	125.3 (3)	C17—C16—C15	121.0 (3)
O2—C4—C3	118.4 (3)	C17—C16—Cl1	119.6 (3)
N4—C4—C3	116.2 (3)	C15—C16—Cl1	119.5 (3)
N1—C5—N3	120.3 (3)	C16—C17—C18	119.6 (3)
N1—C5—S1	115.3 (2)	C16—C17—H17	120.2
N3—C5—S1	124.4 (3)	C18—C17—H17	120.2
N2—C6—C7	122.7 (3)	C13—C18—C17	120.0 (3)
N2—C6—S1	113.92 (19)	C13—C18—H18	120.0
C7—C6—S1	123.4 (2)	C17—C18—H18	120.0
C8—C7—C12	119.3 (2)

C5—N1—N2—C6	−0.1 (4)	C5—S1—C6—C7	−179.0 (3)
C5—N3—C1—O1	−0.5 (5)	N2—C6—C7—C8	5.0 (5)
C5—N3—C1—C2	178.1 (3)	S1—C6—C7—C8	−175.8 (2)
O1—C1—C2—O3	−167.3 (3)	N2—C6—C7—C12	−173.5 (3)
N3—C1—C2—O3	14.1 (4)	S1—C6—C7—C12	5.8 (4)
O1—C1—C2—C3	71.5 (4)	C12—C7—C8—C9	0.6 (5)
N3—C1—C2—C3	−107.1 (3)	C6—C7—C8—C9	−177.9 (3)
O3—C2—C3—O4	−55.8 (3)	C7—C8—C9—C10	−0.8 (6)
C1—C2—C3—O4	63.0 (3)	C8—C9—C10—C11	0.6 (6)
O3—C2—C3—C4	66.4 (3)	C9—C10—C11—C12	−0.2 (6)
C1—C2—C3—C4	−174.8 (3)	C10—C11—C12—C7	0.0 (6)
C13—N4—C4—O2	−3.5 (5)	C8—C7—C12—C11	−0.2 (5)
C13—N4—C4—C3	173.6 (2)	C6—C7—C12—C11	178.3 (3)
O4—C3—C4—O2	−177.4 (3)	C4—N4—C13—C18	34.5 (4)
C2—C3—C4—O2	62.1 (4)	C4—N4—C13—C14	−145.7 (3)
O4—C3—C4—N4	5.3 (3)	C18—C13—C14—C15	1.1 (5)
C2—C3—C4—N4	−115.3 (3)	N4—C13—C14—C15	−178.7 (3)
N2—N1—C5—N3	−179.7 (3)	C13—C14—C15—C16	−1.5 (5)
N2—N1—C5—S1	0.4 (4)	C14—C15—C16—C17	1.2 (5)
C1—N3—C5—N1	−176.0 (3)	C14—C15—C16—Cl1	−178.6 (2)
C1—N3—C5—S1	3.9 (5)	C15—C16—C17—C18	−0.5 (5)
C6—S1—C5—N1	−0.4 (3)	Cl1—C16—C17—C18	179.4 (3)
C6—S1—C5—N3	179.6 (3)	C14—C13—C18—C17	−0.2 (5)
N1—N2—C6—C7	179.1 (3)	N4—C13—C18—C17	179.5 (3)
N1—N2—C6—S1	−0.2 (4)	C16—C17—C18—C13	−0.1 (5)
C5—S1—C6—N2	0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1ⁱ	0.82	1.95	2.733 (3)	159
N3—H3B···O3ⁱⁱ	0.86	2.35	3.061 (4)	140
O4—H4···O1ⁱⁱⁱ	0.82	2.02	2.790 (3)	155
N4—H4A···O2^iv	0.86	2.17	2.951 (4)	151

Symmetry codes: (i) −x+3/2, y−1/2, −z+1; (ii) −x+3/2, y+1/2, −z+1; (iii) −x+3/2, y+1/2, −z+2; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClN₄O₄S
M_r	418.85
Crystal system, space group	Monoclinic, C2
Temperature (K)	298
a, b, c (Å)	41.381 (3), 5.1744 (5), 8.7442 (9)
β (°)	98.315 (1)
V (Å³)	1852.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.46 × 0.40 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.855, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	4632, 2697, 2319
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.091, 1.04
No. of reflections	2697
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15
Absolute structure	Flack (1983), 863 Friedel pairs
Absolute structure parameter	0.03 (8)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1ⁱ	0.82	1.95	2.733 (3)	159
N3—H3B···O3ⁱⁱ	0.86	2.35	3.061 (4)	140
O4—H4···O1ⁱⁱⁱ	0.82	2.02	2.790 (3)	155
N4—H4A···O2^iv	0.86	2.17	2.951 (4)	151

Symmetry codes: (i) −x+3/2, y−1/2, −z+1; (ii) −x+3/2, y+1/2, −z+1; (iii) −x+3/2, y+1/2, −z+2; (iv) x, y+1, z.

Acknowledgements

The work was supported by the Science and Technology Research Project of Jiangxi Provincial Educational Department (grant No. GJJ09076), the Natural Science Foundation of Jiangxi Province, China (grant No. 0620074) and the Scientific Research Fund of Nanchang University.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, S.-H., Huang, H.-M., Kuang, B.-H., Tu, G.-G. & Liu, C.-M. (2008). Acta Cryst. E64, o2006. Web of Science CrossRef IUCr Journals Google Scholar
Marson, C. M. & Melling, R. C. (2005). J. Org. Chem. 70, 9771–9779. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shriner, R. L. & Furrow, C. L. (1955). Org. Synth. 35, 49–50. CAS Google Scholar
Tu, G. G., Li, S. H., Huang, H. M., Li, G., Xiong, F., Mai, X., Zhu, H. W., Kuang, B. H. & Xu, W. F. (2008). Bioorg. Med. Chem. 16, 6663–6668. Web of Science CrossRef PubMed CAS Google Scholar
Watadani, T., Nunomura, S., Takahashi, Y. & Fujii, I. (2005). Anal. Sci. X. 21, x131–x132. CSD CrossRef CAS Google Scholar

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Volume 66| Part 4| April 2010| Page o765

doi:10.1107/S1600536810007919

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

(2R,3R)-N-(4-Chloro­phen­yl)-2,3-dihydr­­oxy-N′-(5-phenyl-1,3,4-thia­diazol-2-yl)succinamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2R,3R)-N-(4-Chlorophenyl)-2,3-dihydroxy-N′-(5-phenyl-1,3,4-thiadiazol-2-yl)succinamide