(2R,3R)-N-(4-Chloro-phen-yl)-2,3-dihydr-oxy-N'-(5-phenyl-1,3,4-thia-diazol-2-yl)succinamide.

In the structure of the title compound, C(18)H(15)ClN(4)O(4)S, the dihedral angle between the two benzene rings is 1.4 (3)°. The angle between the phenyl ring and thia-diazole 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, mol-ecules are linked by inter-molecular 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 = 418.85

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.04

2697 reflections

253 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 863 Friedel pairs

Flack parameter: 0.03 (8)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H15ClN4O4S	F(000) = 864
Mr = 418.85	Dx = 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

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

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(Fo2) + (0.0471P)2 + 0.5765P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2697 reflections	Δρmax = 0.19 e Å−3
253 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 863 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (8)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O2iv	0.86	2.17	2.951 (4)	151

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⋯O2iv	0.86	2.17	2.951 (4)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .