threo-Diethyl 2-ethyl-2-hy-droxy-3-(4-methyl-benzene-sulfonamido)-succinate.

The asymmetric unit of the title compound, C(17)H(25)NO(7)S, contains two independent mol-ecules, which are enanti-omers forming a hydrogen-bonded dimer associated with two R(2) (2)(7) patterns. In each mol-ecule, one ethyl group from the two available ethyl ester functional groups is disordered. In one mol-ecule, the ethyl group of the ester function from an α-carb-oxy-lic acid is positionally disordered over two sets of sites with occupancies of 0.66:0.34. In the second mol-ecule, it is the ethyl group in the γ-ester function that is disordered over two sets of sites with occupancies of 0.58:0.42.

Related literature

For our studies on optically pure β-substituted β-hy­droxy aspartates as glutamate transporter blockers, see: Wehbe et al. (2003a ▶,b ▶,c ▶); Mekki et al. (2011a ▶,b ▶). For hydrogen-bond motifs, see: Etter (1990 ▶); Bernstein et al. (1995 ▶). For the visualization of non-covalent inter­actions, see: Johnson et al. (2010 ▶); Jmol (2011) ▶. For a description of the Jmol toolkit for the preparation of enhanced figures, see: McMahon & Hanson (2008 ▶).

Experimental

Crystal data

C17H25NO7S

M = 387.44

Triclinic,

a = 9.5424 (3) Å

b = 12.2708 (4) Å

c = 18.2427 (5) Å

α = 90.800 (2)°

β = 91.153 (2)°

γ = 112.513 (3)°

V = 1972.36 (10) Å3

Z = 4

Cu Kα radiation

μ = 1.79 mm−1

T = 173 K

0.27 × 0.24 × 0.12 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.110, T max = 1.000

25194 measured reflections

6999 independent reflections

6214 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.02

6999 reflections

527 parameters

81 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Jmol (Jmol, 2011 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029527/dn2708sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029527/dn2708Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029527/dn2708Isup3.cml

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

Enhanced figure: interactive version of Fig. 4

C17H25NO7S	Z = 4
Mr = 387.44	F(000) = 824
Triclinic, P1	Dx = 1.305 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.5424 (3) Å	Cell parameters from 6999 reflections
b = 12.2708 (4) Å	θ = 4.6–67.3°
c = 18.2427 (5) Å	µ = 1.79 mm−1
α = 90.800 (2)°	T = 173 K
β = 91.153 (2)°	Prism, colourless
γ = 112.513 (3)°	0.27 × 0.24 × 0.12 mm
V = 1972.36 (10) Å3

Agilent Xcalibur Sapphire3 Gemini diffractometer	6999 independent reflections
Radiation source: Enhance (Cu) X-ray Source	6214 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 16.0143 pixels mm-1	θmax = 67.3°, θmin = 4.6°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
Tmin = 0.110, Tmax = 1.000	l = −21→21
25194 measured 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.066P)2 + 0.4378P] where P = (Fo2 + 2Fc2)/3
6999 reflections	(Δ/σ)max = 0.001
527 parameters	Δρmax = 0.34 e Å−3
81 restraints	Δρmin = −0.31 e Å−3

Experimental. CrysAlis PRO (Agilent, 2010); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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)
S11	0.49201 (5)	0.41250 (4)	0.16266 (2)	0.03996 (12)
O11	0.36355 (15)	0.60190 (15)	0.33568 (7)	0.0597 (4)
O21	0.48790 (14)	0.69378 (11)	0.23799 (7)	0.0461 (3)
O31	0.77622 (13)	0.69982 (11)	0.32660 (7)	0.0436 (3)
H31	0.852 (2)	0.702 (2)	0.3077 (13)	0.065*
O41	0.90123 (14)	0.54137 (12)	0.31132 (7)	0.0494 (3)
O51	0.69568 (14)	0.39398 (11)	0.35277 (7)	0.0455 (3)
O61	0.43567 (17)	0.30752 (11)	0.20417 (8)	0.0552 (3)
O71	0.57708 (15)	0.41810 (12)	0.09820 (7)	0.0516 (3)
N11	0.60481 (15)	0.51686 (13)	0.21844 (7)	0.0377 (3)
H11	0.656 (2)	0.5792 (15)	0.1966 (11)	0.045*
C11	0.46431 (18)	0.61992 (16)	0.28350 (9)	0.0400 (4)
C21	0.54737 (18)	0.53549 (15)	0.28902 (9)	0.0376 (3)
H21	0.4746	0.4577	0.3062	0.045*
C31	0.68397 (18)	0.58310 (15)	0.34482 (9)	0.0379 (3)
C41	0.77443 (19)	0.50450 (16)	0.33431 (9)	0.0400 (4)
C51	0.6352 (2)	0.58202 (18)	0.42443 (9)	0.0463 (4)
H5A1	0.5827	0.6371	0.4301	0.056*
H5B1	0.5622	0.5019	0.4355	0.056*
C61	0.7683 (2)	0.6170 (2)	0.47904 (11)	0.0575 (5)
H6A1	0.8154	0.5588	0.4767	0.086*
H6B1	0.7321	0.6200	0.5286	0.086*
H6C1	0.8431	0.6949	0.4670	0.086*
C7A1	0.2915 (6)	0.6916 (5)	0.3353 (4)	0.0568 (13)	0.66
H7A1	0.3701	0.7717	0.3301	0.068*	0.66
H7B1	0.2179	0.6752	0.2935	0.068*	0.66
C8A1	0.2124 (4)	0.6844 (4)	0.40588 (19)	0.0621 (9)	0.66
H8A1	0.1381	0.6038	0.4117	0.093*	0.66
H8B1	0.1603	0.7394	0.4056	0.093*	0.66
H8C1	0.2869	0.7052	0.4467	0.093*	0.66
C7B1	0.2456 (11)	0.6449 (11)	0.3313 (8)	0.071 (3)	0.34
H7C1	0.1489	0.5876	0.3497	0.085*	0.34
H7D1	0.2295	0.6673	0.2808	0.085*	0.34
C8B1	0.3134 (11)	0.7484 (10)	0.3809 (5)	0.093 (3)	0.34
H8D1	0.3265	0.7224	0.4302	0.139*	0.34
H8E1	0.2465	0.7922	0.3827	0.139*	0.34
H8F1	0.4124	0.7996	0.3628	0.139*	0.34
C91	0.7677 (2)	0.30975 (18)	0.33901 (11)	0.0525 (4)
H9A1	0.8184	0.3263	0.2913	0.063*
H9B1	0.6889	0.2287	0.3362	0.063*
C101	0.8821 (3)	0.3172 (2)	0.39851 (14)	0.0725 (7)
H10A1	0.9676	0.3936	0.3967	0.109*
H10B1	0.9188	0.2535	0.3913	0.109*
H10C1	0.8347	0.3095	0.4463	0.109*
C111	0.33817 (18)	0.45303 (14)	0.14075 (9)	0.0370 (3)
C121	0.3501 (2)	0.52924 (16)	0.08434 (9)	0.0423 (4)
H121	0.4370	0.5551	0.0547	0.051*
C131	0.2333 (2)	0.56743 (17)	0.07165 (11)	0.0508 (4)
H131	0.2408	0.6197	0.0327	0.061*
C141	0.1055 (2)	0.53164 (17)	0.11419 (11)	0.0504 (4)
C151	0.0970 (2)	0.4554 (2)	0.17044 (12)	0.0573 (5)
H151	0.0105	0.4301	0.2004	0.069*
C161	0.2117 (2)	0.41539 (18)	0.18398 (11)	0.0516 (4)
H161	0.2039	0.3625	0.2226	0.062*
C171	−0.0214 (3)	0.5743 (2)	0.10073 (16)	0.0741 (7)
H17A1	−0.1189	0.5069	0.0997	0.111*
H17B1	−0.0075	0.6141	0.0536	0.111*
H17C1	−0.0201	0.6298	0.1402	0.111*
S12	0.84903 (5)	1.02772 (4)	0.29860 (2)	0.04747 (13)
O12	1.16142 (13)	0.94133 (13)	0.16081 (7)	0.0505 (3)
O22	1.02729 (14)	0.80796 (11)	0.24124 (7)	0.0470 (3)
O32	0.71903 (13)	0.74485 (10)	0.13370 (7)	0.0409 (3)
H32	0.640 (2)	0.746 (2)	0.1483 (13)	0.061*
O42	0.57282 (14)	0.88091 (13)	0.09183 (8)	0.0538 (3)
O52	0.79035 (14)	1.03488 (11)	0.07151 (8)	0.0486 (3)
O62	0.8723 (2)	1.12985 (13)	0.25634 (8)	0.0641 (4)
O72	0.73105 (17)	0.98906 (16)	0.35091 (8)	0.0660 (4)
N12	0.81369 (16)	0.91758 (14)	0.24099 (8)	0.0403 (3)
H12	0.781 (2)	0.8512 (15)	0.2626 (11)	0.048*
C12	1.03877 (18)	0.88414 (15)	0.19833 (9)	0.0376 (3)
C22	0.91316 (17)	0.92874 (14)	0.17950 (9)	0.0353 (3)
H22	0.9614	1.0140	0.1670	0.042*
C32	0.81149 (17)	0.85996 (14)	0.11295 (9)	0.0340 (3)
C42	0.70850 (18)	0.92560 (15)	0.09133 (9)	0.0381 (4)
C52	0.90368 (19)	0.85057 (15)	0.04729 (9)	0.0389 (4)
H5A2	0.9816	0.9296	0.0379	0.047*
H5B2	0.9570	0.7979	0.0597	0.047*
C62	0.8076 (2)	0.8036 (2)	−0.02228 (11)	0.0579 (5)
H6A2	0.7248	0.7284	−0.0124	0.087*
H6B2	0.8708	0.7914	−0.0607	0.087*
H6C2	0.7651	0.8606	−0.0386	0.087*
C72	1.2928 (2)	0.9086 (2)	0.17253 (11)	0.0564 (5)
H7A2	1.3525	0.9224	0.1274	0.068*
H7B2	1.2575	0.8236	0.1836	0.068*
C82	1.3905 (2)	0.9804 (2)	0.23496 (14)	0.0684 (6)
H8A2	1.4197	1.0645	0.2253	0.103*
H8B2	1.4818	0.9626	0.2400	0.103*
H8C2	1.3339	0.9612	0.2804	0.103*
C9A2	0.7216 (7)	1.1129 (6)	0.0412 (3)	0.0498 (13)	0.58
H9A2	0.6213	1.0660	0.0182	0.060*	0.58
H9B2	0.7872	1.1633	0.0035	0.060*	0.58
C10A2	0.7047 (8)	1.1870 (5)	0.1027 (3)	0.0780 (14)	0.58
H10A2	0.6370	1.1364	0.1389	0.117*	0.58
H10B2	0.6617	1.2423	0.0839	0.117*	0.58
H10C2	0.8044	1.2313	0.1259	0.117*	0.58
C9B2	0.6878 (9)	1.1038 (7)	0.0679 (5)	0.0497 (18)	0.42
H9C2	0.6388	1.0954	0.0186	0.060*	0.42
H9D2	0.6080	1.0760	0.1049	0.060*	0.42
C10B2	0.7904 (7)	1.2279 (5)	0.0836 (4)	0.0624 (15)	0.42
H10D2	0.7326	1.2788	0.0802	0.094*	0.42
H10E2	0.8714	1.2524	0.0478	0.094*	0.42
H10F2	0.8351	1.2347	0.1331	0.094*	0.42
C112	1.0231 (2)	1.05241 (15)	0.34519 (9)	0.0417 (4)
C122	1.0273 (2)	0.98059 (18)	0.40217 (10)	0.0511 (4)
H122	0.9382	0.9163	0.4153	0.061*
C132	1.1631 (3)	1.0037 (2)	0.43969 (11)	0.0589 (5)
H132	1.1667	0.9545	0.4788	0.071*
C142	1.2943 (2)	1.0971 (2)	0.42160 (11)	0.0571 (5)
C152	1.2877 (3)	1.1647 (2)	0.36312 (13)	0.0642 (6)
H152	1.3773	1.2276	0.3490	0.077*
C162	1.1536 (3)	1.14287 (18)	0.32469 (12)	0.0576 (5)
H162	1.1512	1.1900	0.2842	0.069*
C172	1.4417 (3)	1.1235 (3)	0.46385 (17)	0.0910 (9)
H17A2	1.4979	1.0804	0.4411	0.137*
H17B2	1.4202	1.0988	0.5147	0.137*
H17C2	1.5026	1.2084	0.4632	0.137*

	U11	U22	U33	U12	U13	U23
S11	0.0442 (2)	0.0407 (2)	0.0390 (2)	0.02082 (18)	−0.00107 (16)	−0.00119 (16)
O11	0.0464 (7)	0.1004 (11)	0.0453 (7)	0.0415 (8)	0.0135 (6)	0.0136 (7)
O21	0.0424 (7)	0.0480 (7)	0.0516 (7)	0.0211 (6)	0.0082 (5)	0.0059 (6)
O31	0.0354 (6)	0.0449 (7)	0.0483 (7)	0.0129 (5)	0.0031 (5)	0.0038 (5)
O41	0.0380 (7)	0.0594 (8)	0.0538 (7)	0.0218 (6)	0.0046 (5)	0.0051 (6)
O51	0.0443 (7)	0.0473 (7)	0.0473 (7)	0.0199 (6)	0.0049 (5)	0.0043 (5)
O61	0.0664 (9)	0.0404 (7)	0.0598 (8)	0.0218 (6)	−0.0082 (7)	0.0038 (6)
O71	0.0541 (7)	0.0655 (8)	0.0453 (7)	0.0347 (7)	−0.0003 (6)	−0.0098 (6)
N11	0.0351 (7)	0.0436 (8)	0.0351 (7)	0.0157 (6)	0.0040 (5)	0.0029 (6)
C11	0.0298 (8)	0.0521 (10)	0.0372 (8)	0.0147 (7)	0.0026 (6)	−0.0017 (7)
C21	0.0331 (8)	0.0440 (9)	0.0343 (8)	0.0130 (7)	0.0048 (6)	0.0041 (7)
C31	0.0338 (8)	0.0430 (9)	0.0363 (8)	0.0137 (7)	0.0034 (6)	0.0041 (7)
C41	0.0370 (9)	0.0505 (10)	0.0329 (8)	0.0173 (8)	0.0003 (6)	0.0023 (7)
C51	0.0443 (9)	0.0598 (11)	0.0371 (9)	0.0225 (9)	0.0038 (7)	−0.0004 (8)
C61	0.0570 (12)	0.0768 (14)	0.0392 (9)	0.0267 (11)	−0.0043 (8)	−0.0029 (9)
C7A1	0.043 (3)	0.081 (3)	0.059 (3)	0.038 (3)	0.011 (3)	0.003 (3)
C8A1	0.0473 (18)	0.090 (3)	0.0539 (18)	0.0325 (18)	0.0016 (14)	−0.0199 (17)
C7B1	0.027 (5)	0.127 (10)	0.060 (5)	0.031 (5)	0.002 (4)	0.000 (6)
C8B1	0.101 (7)	0.148 (8)	0.064 (5)	0.087 (7)	0.004 (5)	−0.023 (5)
C91	0.0594 (11)	0.0510 (11)	0.0532 (10)	0.0282 (9)	−0.0003 (9)	−0.0025 (8)
C101	0.0917 (17)	0.0723 (15)	0.0710 (14)	0.0523 (14)	−0.0224 (13)	−0.0108 (11)
C111	0.0365 (8)	0.0381 (8)	0.0355 (8)	0.0136 (7)	−0.0009 (6)	−0.0028 (6)
C121	0.0421 (9)	0.0459 (9)	0.0391 (8)	0.0168 (8)	0.0035 (7)	0.0038 (7)
C131	0.0544 (11)	0.0487 (10)	0.0521 (10)	0.0233 (9)	−0.0060 (8)	0.0019 (8)
C141	0.0436 (10)	0.0522 (11)	0.0578 (11)	0.0224 (9)	−0.0107 (8)	−0.0171 (9)
C151	0.0368 (9)	0.0736 (14)	0.0580 (11)	0.0172 (9)	0.0078 (8)	−0.0025 (10)
C161	0.0446 (10)	0.0577 (11)	0.0478 (10)	0.0135 (9)	0.0059 (8)	0.0118 (8)
C171	0.0594 (13)	0.0789 (16)	0.0958 (18)	0.0416 (12)	−0.0172 (12)	−0.0252 (13)
S12	0.0538 (3)	0.0588 (3)	0.0417 (2)	0.0352 (2)	−0.00150 (18)	−0.00783 (19)
O12	0.0307 (6)	0.0710 (9)	0.0533 (7)	0.0228 (6)	0.0078 (5)	0.0169 (6)
O22	0.0410 (7)	0.0504 (7)	0.0556 (7)	0.0234 (6)	0.0064 (5)	0.0122 (6)
O32	0.0347 (6)	0.0384 (6)	0.0473 (6)	0.0110 (5)	0.0080 (5)	0.0058 (5)
O42	0.0334 (7)	0.0666 (9)	0.0657 (8)	0.0239 (6)	0.0021 (6)	0.0016 (7)
O52	0.0450 (7)	0.0396 (7)	0.0665 (8)	0.0227 (6)	−0.0096 (6)	0.0006 (6)
O62	0.0951 (11)	0.0635 (9)	0.0549 (8)	0.0549 (9)	−0.0132 (7)	−0.0097 (7)
O72	0.0586 (8)	0.1001 (12)	0.0516 (8)	0.0444 (8)	0.0058 (6)	−0.0156 (8)
N12	0.0361 (7)	0.0474 (8)	0.0401 (7)	0.0190 (7)	0.0050 (6)	−0.0018 (6)
C12	0.0312 (8)	0.0421 (9)	0.0405 (8)	0.0152 (7)	0.0031 (6)	0.0007 (7)
C22	0.0305 (8)	0.0386 (8)	0.0390 (8)	0.0157 (7)	0.0041 (6)	0.0022 (6)
C32	0.0304 (7)	0.0340 (8)	0.0383 (8)	0.0130 (6)	0.0046 (6)	0.0025 (6)
C42	0.0351 (9)	0.0446 (9)	0.0375 (8)	0.0187 (7)	0.0005 (6)	−0.0044 (7)
C52	0.0395 (9)	0.0386 (8)	0.0422 (9)	0.0186 (7)	0.0076 (7)	0.0013 (7)
C62	0.0553 (11)	0.0633 (12)	0.0468 (10)	0.0137 (10)	0.0076 (9)	−0.0129 (9)
C72	0.0330 (9)	0.0871 (15)	0.0577 (11)	0.0321 (10)	0.0067 (8)	0.0061 (10)
C82	0.0431 (11)	0.0901 (17)	0.0765 (15)	0.0310 (11)	−0.0062 (10)	0.0021 (13)
C9A2	0.044 (3)	0.056 (3)	0.058 (3)	0.029 (2)	0.004 (2)	0.011 (2)
C10A2	0.114 (5)	0.071 (3)	0.076 (3)	0.064 (3)	0.013 (3)	0.010 (3)
C9B2	0.046 (4)	0.043 (3)	0.073 (5)	0.031 (3)	0.001 (3)	0.010 (4)
C10B2	0.069 (4)	0.041 (3)	0.088 (4)	0.032 (3)	0.008 (3)	0.013 (3)
C112	0.0488 (10)	0.0419 (9)	0.0374 (8)	0.0210 (8)	0.0004 (7)	−0.0026 (7)
C122	0.0528 (11)	0.0497 (10)	0.0469 (10)	0.0149 (9)	0.0033 (8)	0.0080 (8)
C132	0.0656 (13)	0.0682 (13)	0.0451 (10)	0.0278 (11)	−0.0011 (9)	0.0123 (9)
C142	0.0537 (11)	0.0657 (13)	0.0493 (10)	0.0203 (10)	−0.0027 (9)	−0.0041 (9)
C152	0.0546 (12)	0.0539 (12)	0.0713 (14)	0.0064 (10)	0.0014 (10)	0.0090 (10)
C162	0.0643 (13)	0.0478 (11)	0.0568 (11)	0.0168 (10)	0.0002 (9)	0.0140 (9)
C172	0.0648 (15)	0.119 (2)	0.0807 (18)	0.0267 (16)	−0.0178 (13)	0.0017 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O32	0.84 (2)	2.23 (2)	3.0426 (18)	162.(2)
O31—H31···O22	0.80 (2)	2.10 (2)	2.7747 (17)	142 (2)
N12—H12···O31	0.86 (2)	2.19 (2)	3.019 (2)	161 (2)
O32—H32···O21	0.81 (2)	2.15 (2)	2.8321 (17)	142 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O32	0.84 (2)	2.23 (2)	3.0426 (18)	162 (2)
O31—H31⋯O22	0.80 (2)	2.10 (2)	2.7747 (17)	142 (2)
N12—H12⋯O31	0.86 (2)	2.19 (2)	3.019 (2)	161 (2)
O32—H32⋯O21	0.81 (2)	2.15 (2)	2.8321 (17)	142 (2)