(2R,3R)-3-O-Benzoyl-N-benzyl­tartramide

Madura, I.D.; Zachara, J.; Bernaś, U.; Hajmowicz, H.; Synoradzki, L.

doi:10.1107/S1600536812022933

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1891-o1892

doi:10.1107/S1600536812022933

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(2R,3R)-3-O-Benzoyl-N-benzyltartramide †

Izabela D. Madura,^a ^* Janusz Zachara,^a Urszula Bernaś,^a Halina Hajmowicz ^a and Ludwik Synoradzki ^a

^aWarsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warszawa, Poland
^*Correspondence e-mail: izabela@ch.pw.edu.pl

(Received 17 May 2012; accepted 19 May 2012; online 26 May 2012)

The title compound, C₁₈H₁₇NO₆ [systematic name: (2R,3R)-4-benzylamino-2-benzoyloxy-3-hydroxy-4-oxobutanoic acid], is the first structurally characterized unsymmetrical monoamide–monoacyl tartaric acid derivative. The molecule shows a staggered conformation around the tartramide Csp³—Csp³ bond with trans-oriented carboxyl and amide groups. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by O—H⋯O hydrogen bonds between the carboxyl and amide carbonyl groups, forming translational chains along [001]. Further O—H⋯O and N—H⋯O hydrogen bonds as well as weaker C—H⋯O and C—H⋯π intermolecular interactions extend the supramolecular assembly into a double-layer structure parallel to (100). There are no directional interactions between the double layers.

Related literature

For crystal structures of R,R-tartaric mono amides, see: Rychlewska et al. (1999 ); Rychlewska & Warżajtis (2000 , 2001 ). For examples of the crystal structures of monoacyl derivatives, see: Madura et al. (2010 ); Knyazev et al. (1988 ); Chekhlov et al. (1986 ); Ishihara et al. (1993 ). For the synthesis, see: Bell (1987 ); Bernaś et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₇NO₆
M_r = 343.33
Monoclinic, C 2
a = 35.7118 (6) Å
b = 6.17734 (11) Å
c = 7.48599 (15) Å
β = 93.0377 (15)°
V = 1649.12 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.88 mm⁻¹
T = 100 K
0.54 × 0.22 × 0.18 mm

Data collection

Agilent Gemini A Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.724, T_max = 1.000
29440 measured reflections
2945 independent reflections
2928 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.071
S = 1.06
2945 reflections
235 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1321 Friedel pairs
Flack parameter: −0.01 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.99 (2)	1.55 (2)	2.5317 (13)	171.2 (17)
O4—H4⋯O2ⁱⁱ	0.81 (2)	1.96 (2)	2.7501 (14)	165 (2)
N1—H1A⋯O6ⁱⁱⁱ	0.88 (2)	2.002 (19)	2.7788 (17)	146.4 (18)
N1—H1A⋯O4	0.88 (2)	2.12 (2)	2.5894 (14)	112.8 (15)
C12—H12A⋯O1^iv	0.99	2.52	3.4827 (16)	165
C12—H12B⋯O1^v	0.99	2.44	3.3117 (16)	146
Symmetry codes: (i) x, y, z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+2]$ ; (iii) x, y+1, z; (iv) x, y+1, z-1; (v) x, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022933/gk2491sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022933/gk2491Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022933/gk2491Isup3.mol

Supporting information file. DOI: 10.1107/S1600536812022933/gk2491Isup4.cml

checkCIF report

Comment top

The title molecule crystallizes in non-centrosymmetric C2 space group as R,R enantiomer. Molecular structure with the atom numbering scheme is presented in Fig. 1. Similarly to the previously characterized tartaric acid mono amides (Rychlewska et al., 1999; Rychlewska & Warżajtis, 2000, 2001), the title molecule adopts the staggered conformation around the C2–C3 bond (Fig. 2.). Thus, the carboxylic group is in trans (T) orientation with respect to the amide group, whereas the hydroxy and benzoyl substituents adopt the gauche counterclockwise orientation. The conformation on C–C* bond in amide fragment enables the formation of an intramolecular N–H···O hydrogen bond between N–H donor and the hydroxyl group. Hence the carbonyl group is on the opposite side of the proximal C*–O bond. Such orientation, called antiplanar (a) is also observed in the carboxylic fragment, and the overall conformation of molecules can be given as T(a,a). It is worth noting that in case of dibenzoyl tartaric mono amides (Rychlewska & Warżajtis, 2001) or those with unsubstituted OH groups (Rychlewska et al., 1999; Rychlewska & Warżajtis, 2000) the conformation of the acid fragment is such that the carbonyl group eclipses the nearest C–O bond (synplanar conformation, s), while the presence of at least one N–H bond forces the conformation of the amide fragment to be antiplanar with the intramolecular N–H···O bond.

The analysis of intermolecular interactions shows that the title molecules related by translation along [001] form infinite head-to-tail chains via hydrogen bonds between carboxylic OH donors and amide carbonyl groups. A topologically analogous chain motif was observed in the crystal structures of dibenzoyl mono amides by Rychlewska & Warżajtis (2001). Further, the O–H hydroxyl group acts as a donor to carboxyl C=O group joining the chains related by 2₁ screw axis into a double layer (Fig. 3). The layer is enhanced by N—H···O_{benzoyl carbonyl} as well as weaker C—H···O and C—H···π intermolecular interactions. The neighbouring layers are held together by weak van der Waals forces only.

Related literature top

For crystal structures of R,R-tartaric mono amides, see: Rychlewska et al. (1999); Rychlewska & Warżajtis (2000, 2001). For examples of the crystal structures of monoacyl derivatives, see: Madura et al. (2010); Knyazev et al. (1988); Chekhlov et al. (1986); Ishihara et al. (1993). For the synthesis, see: Bell (1987); Bernaś et al. (2010).

Experimental top

A (1:2 mol/mol) mixture of O-benzoyl-L-tartaric anhydride (Bernaś et al., 2010) and benzylamine in acetonitrile was stirred at room temperature for 10 min. The mixture was then acidified with 10% HCl and filtered. The resulting white solid product was rinsed with water to give pure title compound with m.p. 465–467 K. Preparation and characterization of regioisomer of the title compound was described by Bell (1987), although its structure was defined incorrectly. [α]²⁵_D = +40.9°, (c 1, EtOH). IR (EtOH): ν = 693, 708 (C=C, Ph); 1112, 1263 (C—O); 1663 (C=O, CONH); 1710 (C=O, COOH); 1723 (C=O, COBz) cm^{-1. 1}H NMR (400 MHz, DMSO-d6): δ = 4.43–4.15 (m, 2H), 4.62 (d, 1H), 5.53 (d, 1H), 6.42 (br), 6.81–6.91 (m, 5H), 7.42–7.99 (m, 5H), 8.69 (t, 1H) p.p.m.. ¹³C NMR (400 MHz, DMSO-d6): δ = 41.87 (CH2), 71.33 (CH), 74.04 (CH), 126.44, 127.88, 128.76, 128.76, 129.06, 129.52, 133.71, 139.25 (Ph), 165.01, 168.93, 170.28 (C=O) p.p.m.. Anal. Calcd. (%) for C₁₈H₁₇NO₆: C 62.97; H 4.99; N 4.08. Found: C 62.92; H 4.99; N 4.11. Crystals suitable for single-crystal X-ray diffraction measurement were obtained from saturated ethyl acetate/methanol (3:1).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP plot of the molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are depicted as spheres with arbitrary radii. Dotted line indicates intramolecular hydrogen bond.
	Fig. 2. (a) The staggered conformation (T) around C2—C3 bond; (b) Antiplanar (a) conformations around C1—C2 and C4—C3 bonds.
	Fig. 3. View along the [010] direction showing double-layers of molecules formed by two types of O—H···O (dashed lines) and N—H···O (dotted lines) bonds. Symmetry codes: (i) x, y, z + 1; (ii) -x + 1/2, y + 1/2, -z + 2; (iii) x, y + 1, z.

(2R,3R)-4-benzylamino-2-benzoyloxy-3-hydroxy-4-oxobutanoic acid top

Crystal data top

C₁₈H₁₇NO₆	D_x = 1.383 Mg m⁻³
M_r = 343.33	Melting point: 193 K
Monoclinic, C2	Cu Kα radiation, λ = 1.5418 Å
a = 35.7118 (6) Å	Cell parameters from 23556 reflections
b = 6.17734 (11) Å	θ = 5.0–67.0°
c = 7.48599 (15) Å	µ = 0.88 mm⁻¹
β = 93.0377 (15)°	T = 100 K
V = 1649.12 (5) Å³	Prism, colourless
Z = 4	0.54 × 0.22 × 0.18 mm
F(000) = 720

Data collection top

Agilent Gemini A Ultra diffractometer	2945 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2928 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.3347 pixels mm^-1	θ_max = 67.1°, θ_min = 5.0°
ω scans	h = −42→42
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −7→7
T_min = 0.724, T_max = 1.000	l = −8→8
29440 measured reflections

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.0442P)² + 0.6346P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2945 reflections	Δρ_max = 0.19 e Å⁻³
235 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1321 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (13)

Crystal data top

C₁₈H₁₇NO₆	V = 1649.12 (5) Å³
M_r = 343.33	Z = 4
Monoclinic, C2	Cu Kα radiation
a = 35.7118 (6) Å	µ = 0.88 mm⁻¹
b = 6.17734 (11) Å	T = 100 K
c = 7.48599 (15) Å	0.54 × 0.22 × 0.18 mm
β = 93.0377 (15)°

Data collection top

Agilent Gemini A Ultra diffractometer	2945 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2928 reflections with I > 2σ(I)
T_min = 0.724, T_max = 1.000	R_int = 0.038
29440 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.071	Δρ_max = 0.19 e Å⁻³
S = 1.06	Δρ_min = −0.17 e Å⁻³
2945 reflections	Absolute structure: Flack (1983), 1321 Friedel pairs
235 parameters	Absolute structure parameter: −0.01 (13)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.31056 (3)	0.28482 (16)	1.07911 (12)	0.0222 (2)
H1	0.2993 (5)	0.315 (4)	1.194 (3)	0.046*
O2	0.25203 (3)	0.35877 (17)	0.97437 (12)	0.0229 (2)
O3	0.33951 (2)	0.36177 (15)	0.77766 (11)	0.0195 (2)
O4	0.29381 (3)	0.72671 (16)	0.76263 (12)	0.0213 (2)
H4	0.2772 (6)	0.764 (4)	0.825 (3)	0.046*
O5	0.28714 (3)	0.38296 (17)	0.38200 (11)	0.0254 (2)
O6	0.34669 (3)	0.0721 (2)	0.60328 (18)	0.0446 (3)
N1	0.31211 (3)	0.7200 (2)	0.43257 (14)	0.0196 (2)
H1A	0.3160 (5)	0.818 (3)	0.517 (3)	0.037*
C1	0.28496 (3)	0.3271 (2)	0.95296 (16)	0.0185 (3)
C2	0.29952 (3)	0.3381 (2)	0.76528 (16)	0.0175 (3)
H2	0.2924	0.2040	0.6969	0.021*
C3	0.28249 (3)	0.5372 (2)	0.67065 (16)	0.0185 (3)
H3	0.2545	0.5262	0.6689	0.022*
C4	0.29469 (3)	0.5431 (2)	0.47812 (16)	0.0176 (3)
C5	0.36003 (4)	0.2140 (2)	0.69603 (17)	0.0217 (3)
C6	0.40098 (4)	0.2478 (2)	0.72820 (16)	0.0220 (3)
C7	0.41579 (4)	0.4261 (3)	0.82131 (18)	0.0256 (3)
H7	0.3996	0.5298	0.8704	0.031*
C8	0.45432 (4)	0.4509 (3)	0.8417 (2)	0.0325 (4)
H8	0.4646	0.5732	0.9037	0.039*
C9	0.47800 (4)	0.2982 (3)	0.7721 (2)	0.0341 (4)
H9	0.5044	0.3155	0.7874	0.041*
C10	0.46321 (4)	0.1209 (3)	0.6808 (2)	0.0327 (3)
H10	0.4795	0.0163	0.6337	0.039*
C11	0.42477 (4)	0.0950 (3)	0.6574 (2)	0.0275 (3)
H11	0.4147	−0.0263	0.5935	0.033*
C12	0.32616 (4)	0.7696 (2)	0.25671 (16)	0.0202 (3)
H12A	0.3175	0.9160	0.2196	0.024*
H12B	0.3154	0.6647	0.1680	0.024*
C13	0.36848 (4)	0.7612 (2)	0.25630 (16)	0.0206 (3)
C14	0.38841 (4)	0.5883 (2)	0.33400 (19)	0.0270 (3)
H14	0.3753	0.4735	0.3876	0.032*
C15	0.42720 (4)	0.5825 (3)	0.3336 (2)	0.0310 (3)
H15	0.4406	0.4653	0.3885	0.037*
C16	0.44647 (4)	0.7487 (3)	0.25267 (19)	0.0308 (3)
H16	0.4731	0.7458	0.2530	0.037*
C17	0.42679 (4)	0.9175 (3)	0.1720 (2)	0.0317 (3)
H17	0.4399	1.0290	0.1141	0.038*
C18	0.38793 (4)	0.9259 (2)	0.17444 (19)	0.0260 (3)
H18	0.3746	1.0441	0.1203	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0249 (4)	0.0281 (5)	0.0133 (4)	0.0021 (4)	−0.0010 (3)	0.0001 (4)
O2	0.0203 (4)	0.0337 (5)	0.0152 (4)	0.0001 (4)	0.0047 (3)	0.0039 (4)
O3	0.0167 (4)	0.0254 (5)	0.0165 (4)	0.0000 (4)	0.0009 (3)	−0.0036 (4)
O4	0.0232 (4)	0.0257 (5)	0.0157 (4)	−0.0002 (4)	0.0062 (3)	−0.0049 (4)
O5	0.0358 (5)	0.0284 (5)	0.0123 (4)	−0.0105 (4)	0.0024 (4)	−0.0018 (4)
O6	0.0270 (5)	0.0438 (7)	0.0643 (8)	−0.0105 (5)	0.0154 (5)	−0.0338 (6)
N1	0.0207 (5)	0.0243 (6)	0.0140 (5)	−0.0020 (5)	0.0032 (4)	−0.0020 (5)
C1	0.0228 (6)	0.0175 (6)	0.0152 (6)	−0.0023 (5)	0.0011 (5)	−0.0002 (5)
C2	0.0167 (6)	0.0237 (6)	0.0121 (6)	−0.0015 (5)	0.0010 (4)	−0.0019 (5)
C3	0.0175 (6)	0.0257 (7)	0.0125 (6)	−0.0014 (6)	0.0020 (4)	−0.0010 (5)
C4	0.0151 (5)	0.0248 (6)	0.0128 (6)	0.0000 (5)	−0.0010 (4)	0.0011 (5)
C5	0.0229 (6)	0.0235 (7)	0.0192 (6)	−0.0012 (6)	0.0065 (5)	−0.0028 (6)
C6	0.0223 (6)	0.0284 (8)	0.0156 (6)	0.0019 (6)	0.0046 (5)	0.0034 (5)
C7	0.0234 (7)	0.0343 (8)	0.0192 (6)	0.0007 (6)	0.0030 (5)	−0.0037 (6)
C8	0.0243 (7)	0.0486 (10)	0.0243 (7)	−0.0042 (7)	−0.0010 (6)	−0.0054 (7)
C9	0.0181 (6)	0.0575 (11)	0.0266 (7)	0.0026 (7)	0.0009 (5)	0.0055 (7)
C10	0.0269 (8)	0.0434 (9)	0.0286 (8)	0.0110 (7)	0.0083 (6)	0.0052 (7)
C11	0.0269 (7)	0.0314 (8)	0.0250 (7)	0.0035 (6)	0.0073 (6)	0.0009 (6)
C12	0.0241 (6)	0.0237 (7)	0.0131 (6)	−0.0025 (5)	0.0027 (5)	0.0028 (5)
C13	0.0241 (6)	0.0255 (7)	0.0124 (5)	−0.0019 (5)	0.0029 (5)	−0.0020 (5)
C14	0.0270 (7)	0.0307 (8)	0.0237 (7)	0.0014 (6)	0.0059 (5)	0.0052 (6)
C15	0.0272 (7)	0.0399 (9)	0.0261 (7)	0.0062 (6)	0.0029 (6)	0.0027 (6)
C16	0.0203 (6)	0.0437 (9)	0.0289 (7)	−0.0010 (6)	0.0049 (5)	−0.0088 (7)
C17	0.0289 (8)	0.0345 (8)	0.0329 (8)	−0.0083 (6)	0.0111 (6)	−0.0021 (7)
C18	0.0278 (7)	0.0267 (7)	0.0241 (7)	−0.0017 (6)	0.0055 (6)	0.0019 (6)

Geometric parameters (Å, º) top

O1—C1	1.3053 (15)	C8—H8	0.9500
O1—H1	0.99 (2)	C9—C8	1.387 (2)
O2—C1	1.2111 (16)	C9—H9	0.9500
O3—C2	1.4336 (14)	C10—C9	1.381 (3)
O3—C5	1.3384 (16)	C10—C11	1.384 (2)
O4—C3	1.4067 (17)	C10—H10	0.9500
O4—H4	0.81 (2)	C11—H11	0.9500
O5—C4	1.2442 (17)	C12—H12A	0.9900
O6—C5	1.2010 (18)	C12—H12B	0.9900
N1—C4	1.3115 (18)	C13—C12	1.5126 (17)
N1—C12	1.4659 (16)	C13—C18	1.3922 (19)
N1—H1A	0.88 (2)	C14—C13	1.393 (2)
C2—C1	1.5253 (17)	C14—C15	1.386 (2)
C2—C3	1.5293 (18)	C14—H14	0.9500
C2—H2	1.0000	C15—C16	1.392 (2)
C3—C4	1.5280 (16)	C15—H15	0.9500
C3—H3	1.0000	C16—H16	0.9500
C6—C5	1.4841 (18)	C17—C16	1.379 (2)
C6—C7	1.393 (2)	C17—H17	0.9500
C6—C11	1.393 (2)	C18—H18	0.9500
C7—C8	1.385 (2)	C18—C17	1.390 (2)
C7—H7	0.9500

C1—O1—H1	106.9 (12)	C9—C8—H8	119.8
C5—O3—C2	117.93 (10)	C8—C9—C10	120.05 (13)
C3—O4—H4	108.7 (16)	C8—C9—H9	120.0
C4—N1—C12	126.69 (12)	C10—C9—H9	120.0
C4—N1—H1A	116.4 (13)	C9—C10—C11	120.34 (14)
C12—N1—H1A	116.9 (13)	C9—C10—H10	119.8
O1—C1—O2	125.75 (11)	C11—C10—H10	119.8
O1—C1—C2	114.55 (10)	C6—C11—C10	119.61 (15)
O2—C1—C2	119.70 (11)	C6—C11—H11	120.2
O3—C2—C1	109.39 (9)	C10—C11—H11	120.2
O3—C2—C3	108.56 (10)	N1—C12—C13	112.59 (10)
O3—C2—H2	110.1	N1—C12—H12A	109.1
C1—C2—C3	108.41 (10)	N1—C12—H12B	109.1
C1—C2—H2	110.1	C13—C12—H12A	109.1
C3—C2—H2	110.1	C13—C12—H12B	109.1
O4—C3—C2	110.23 (9)	H12A—C12—H12B	107.8
O4—C3—C4	110.67 (10)	C14—C13—C12	120.92 (12)
O4—C3—H3	108.9	C18—C13—C12	119.84 (12)
C2—C3—H3	108.9	C18—C13—C14	119.23 (12)
C4—C3—C2	109.26 (10)	C13—C14—H14	119.8
C4—C3—H3	108.9	C15—C14—C13	120.48 (13)
O5—C4—N1	127.10 (11)	C15—C14—H14	119.8
O5—C4—C3	117.56 (11)	C14—C15—C16	119.95 (14)
N1—C4—C3	115.34 (11)	C14—C15—H15	120.0
O3—C5—O6	123.49 (12)	C16—C15—H15	120.0
O3—C5—C6	112.86 (11)	C15—C16—H16	120.1
O6—C5—C6	123.63 (12)	C17—C16—C15	119.71 (13)
C5—C6—C7	122.51 (12)	C17—C16—H16	120.1
C5—C6—C11	117.27 (13)	C18—C17—H17	119.7
C7—C6—C11	120.20 (13)	C16—C17—C18	120.58 (14)
C6—C7—C8	119.44 (14)	C16—C17—H17	119.7
C6—C7—H7	120.3	C13—C18—H18	120.0
C8—C7—H7	120.3	C17—C18—C13	120.01 (13)
C7—C8—C9	120.35 (15)	C17—C18—H18	120.0
C7—C8—H8	119.8

C5—O3—C2—C1	123.19 (12)	C11—C6—C5—O3	176.38 (12)
C5—O3—C2—C3	−118.68 (11)	C11—C6—C5—O6	−5.2 (2)
C2—O3—C5—O6	5.3 (2)	C11—C6—C7—C8	0.5 (2)
C2—O3—C5—C6	−176.29 (10)	C5—C6—C7—C8	−178.03 (13)
C12—N1—C4—C3	−178.86 (11)	C5—C6—C11—C10	178.85 (13)
C12—N1—C4—O5	0.9 (2)	C7—C6—C11—C10	0.2 (2)
C4—N1—C12—C13	−108.11 (14)	C6—C7—C8—C9	−0.9 (2)
O3—C2—C1—O1	−16.83 (15)	C10—C9—C8—C7	0.5 (2)
O3—C2—C1—O2	162.45 (12)	C11—C10—C9—C8	0.3 (2)
C3—C2—C1—O1	−135.05 (11)	C9—C10—C11—C6	−0.6 (2)
C3—C2—C1—O2	44.24 (16)	C14—C13—C12—N1	46.90 (17)
O3—C2—C3—O4	−56.88 (12)	C18—C13—C12—N1	−134.32 (13)
O3—C2—C3—C4	64.93 (12)	C12—C13—C18—C17	−179.25 (12)
C1—C2—C3—O4	61.86 (12)	C14—C13—C18—C17	−0.4 (2)
C1—C2—C3—C4	−176.32 (10)	C15—C14—C13—C12	−179.72 (13)
O4—C3—C4—O5	178.58 (11)	C15—C14—C13—C18	1.5 (2)
O4—C3—C4—N1	−1.62 (15)	C13—C14—C15—C16	−1.0 (2)
C2—C3—C4—O5	57.03 (14)	C14—C15—C16—C17	−0.5 (2)
C2—C3—C4—N1	−123.17 (12)	C18—C17—C16—C15	1.6 (2)
C7—C6—C5—O3	−5.05 (18)	C13—C18—C17—C16	−1.1 (2)
C7—C6—C5—O6	173.34 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.99 (2)	1.55 (2)	2.5317 (13)	171.2 (17)
O4—H4···O2ⁱⁱ	0.81 (2)	1.96 (2)	2.7501 (14)	165 (2)
N1—H1A···O6ⁱⁱⁱ	0.88 (2)	2.002 (19)	2.7788 (17)	146.4 (18)
N1—H1A···O4	0.88 (2)	2.12 (2)	2.5894 (14)	112.8 (15)
C2—H2···O6	1.00	2.25	2.6879 (17)	105
C12—H12A···O1^iv	0.99	2.52	3.4827 (16)	165
C12—H12B···O1^v	0.99	2.44	3.3117 (16)	146

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇NO₆
M_r	343.33
Crystal system, space group	Monoclinic, C2
Temperature (K)	100
a, b, c (Å)	35.7118 (6), 6.17734 (11), 7.48599 (15)
β (°)	93.0377 (15)
V (Å³)	1649.12 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.54 × 0.22 × 0.18

Data collection
Diffractometer	Agilent Gemini A Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.724, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	29440, 2945, 2928
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.071, 1.06
No. of reflections	2945
No. of parameters	235
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17
Absolute structure	Flack (1983), 1321 Friedel pairs
Absolute structure parameter	−0.01 (13)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.99 (2)	1.55 (2)	2.5317 (13)	171.2 (17)
O4—H4···O2ⁱⁱ	0.81 (2)	1.96 (2)	2.7501 (14)	165 (2)
N1—H1A···O6ⁱⁱⁱ	0.88 (2)	2.002 (19)	2.7788 (17)	146.4 (18)
N1—H1A···O4	0.88 (2)	2.12 (2)	2.5894 (14)	112.8 (15)
C12—H12A···O1^iv	0.99	2.52	3.4827 (16)	165
C12—H12B···O1^v	0.99	2.44	3.3117 (16)	146

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

Footnotes

†Tartaric acid and its O-acyl derivatives. Part 13.

Acknowledgements

This work was supported financially by Warsaw University of Technology.

References

Bell, K. H. (1987). Aust. J. Chem. 40, 1723–1735. CrossRef CAS Google Scholar
Bernaś, U., Hajmowicz, H., Madura, I. D., Majcher, M., Synoradzki, L. & Zawada, K. (2010). Arkivoc, xi, 1–12. Google Scholar
Chekhlov, A. N., Belov, Yu. P., Martynov, I. V. & Aksinenko, A. Y. (1986). Russ. Chem. Bull. 35, 2587–2589. CrossRef Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ishihara, K., Gao, Q. & Yamamoto, H. (1993). J. Am. Chem. Soc. 115, 10412–10413. CSD CrossRef CAS Web of Science Google Scholar
Knyazev, V. N., Drozd, V. N., Lipovtsev, V. N., Kurapov, P. B., Yufit, D. S. & Struchkov, Y. T. (1988). Russ. J. Org. Chem. 24, 2174–2182. CAS Google Scholar
Madura, I. D., Zachara, J., Bernaś, U., Hajmowicz, H., Kliś, T., Serwatowski, J. & Synoradzki, L. (2010). J. Mol. Struct. 984, 75–82. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rychlewska, U., Szarecka, A., Rychlewski, J. & Motała, R. (1999). Acta Cryst. B55, 617–625. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rychlewska, U. & Warżajtis, B. (2000). Acta Cryst. B56, 833–848. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rychlewska, U. & Warżajtis, B. (2001). Acta Cryst. B57, 415–427. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar