2,3-Di-p-toluoyl-(2R,3R)-tartaric acid ethyl acetate solvate

In the title compound, C₂₀H₁₈O₈·C₄H₈O₂, all bond lengths and angles in the di-p-toluoyltartaric acid mol­ecule are normal. The structure is stabilized by O—H...O and C—H...O hydrogen bonds in addition to van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.120
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       6.83 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C23
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               2558
           Count of symmetry unique reflns         2559
           Completeness (_total/calc)             99.96%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2,3-Di-p-toluoyl-(2R,3R)-tartaric acid ethyl acetate solvate

Crystal data

C20H18O8·C4H8O2	F(000) = 1000
Mr = 474.45	Dx = 1.246 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1528 reflections
a = 7.8516 (13) Å	θ = 2.4–22.4°
b = 16.140 (3) Å	µ = 0.10 mm^−1
c = 19.951 (3) Å	T = 298 K
V = 2528.4 (7) Å^3	Block, colourless
Z = 4	0.58 × 0.36 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2558 independent reflections
Radiation source: fine-focus sealed tube	2115 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.946, Tmax = 0.973	k = −19→18
12875 measured reflections	l = −18→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0677P)^2 + 0.1698P] where P = (Fo^2 + 2Fc^2)/3
2558 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5127 (4)	0.63629 (16)	0.42850 (14)	0.0908 (9)
O2	0.5844 (3)	0.57064 (11)	0.33461 (10)	0.0516 (5)
O3	0.4171 (3)	0.75497 (15)	0.26344 (16)	0.0865 (9)
H3	0.306 (6)	0.778 (2)	0.2558 (19)	0.091 (12)*
O4	0.2842 (3)	0.64400 (15)	0.30246 (14)	0.0750 (7)
O5	0.9379 (4)	0.55926 (19)	0.21689 (17)	0.1031 (10)
O6	0.9439 (3)	0.66189 (16)	0.29099 (16)	0.0791 (8)
H6	1.043 (6)	0.648 (2)	0.286 (2)	0.083 (13)*
O7	0.6012 (3)	0.57694 (13)	0.19780 (11)	0.0597 (6)
O8	0.6686 (5)	0.64836 (16)	0.10670 (14)	0.1019 (11)
O9	−0.1294 (3)	0.32505 (17)	0.26404 (15)	0.0850 (8)
O10	0.1252 (3)	0.37257 (16)	0.23880 (13)	0.0738 (7)
C1	0.5147 (8)	0.2521 (3)	0.5277 (3)	0.121 (2)
H1A	0.4645	0.2583	0.5712	0.182*
H1B	0.6293	0.2322	0.5323	0.182*
H1C	0.4493	0.2131	0.5020	0.182*
C2	0.5161 (6)	0.3349 (3)	0.4922 (2)	0.0834 (12)
C3	0.4601 (7)	0.4052 (4)	0.5247 (2)	0.0991 (15)
H3A	0.4169	0.4008	0.5680	0.119*
C4	0.4668 (6)	0.4815 (3)	0.49468 (19)	0.0831 (12)
H4A	0.4281	0.5281	0.5175	0.100*
C5	0.5312 (4)	0.4893 (2)	0.43025 (17)	0.0572 (8)
C6	0.5858 (5)	0.41916 (19)	0.39683 (16)	0.0590 (8)
H6A	0.6282	0.4231	0.3534	0.071*
C7	0.5768 (5)	0.3433 (2)	0.4283 (2)	0.0738 (11)
H7A	0.6132	0.2964	0.4054	0.089*
C8	0.5394 (5)	0.5722 (2)	0.40007 (17)	0.0583 (8)
C9	0.5889 (4)	0.64878 (17)	0.30202 (16)	0.0496 (7)
H9A	0.6501	0.6883	0.3305	0.059*
C10	0.4099 (4)	0.68138 (19)	0.28930 (17)	0.0558 (8)
C11	0.6851 (4)	0.63823 (18)	0.23748 (17)	0.0518 (8)
H11A	0.6820	0.6909	0.2131	0.062*
C12	0.8692 (4)	0.6133 (2)	0.24663 (18)	0.0589 (9)
C13	0.6099 (5)	0.5870 (2)	0.13119 (17)	0.0607 (9)
C14	0.5458 (5)	0.5148 (2)	0.09416 (16)	0.0563 (8)
C15	0.5735 (6)	0.5106 (2)	0.02614 (18)	0.0760 (11)
H15A	0.6263	0.5547	0.0045	0.091*
C16	0.5253 (7)	0.4434 (2)	−0.00995 (19)	0.0846 (13)
H16A	0.5481	0.4419	−0.0557	0.102*
C17	0.4431 (5)	0.3770 (2)	0.01958 (18)	0.0707 (10)
C18	0.4123 (6)	0.3820 (2)	0.0876 (2)	0.0825 (12)
H18A	0.3549	0.3390	0.1088	0.099*
C19	0.4647 (5)	0.4490 (2)	0.12433 (18)	0.0741 (11)
H19A	0.4453	0.4500	0.1703	0.089*
C20	0.3885 (8)	0.3028 (3)	−0.0205 (2)	0.1027 (15)
H20A	0.3324	0.2639	0.0084	0.154*
H20B	0.4867	0.2772	−0.0403	0.154*
H20C	0.3116	0.3200	−0.0552	0.154*
C21	0.1266 (6)	0.4318 (2)	0.3499 (2)	0.0915 (13)
H21A	0.1645	0.4231	0.3951	0.137*
H21B	0.0046	0.4360	0.3492	0.137*
H21C	0.1754	0.4821	0.3328	0.137*
C22	0.1806 (5)	0.3618 (2)	0.30796 (19)	0.0782 (11)
H22A	0.3037	0.3572	0.3093	0.094*
H22B	0.1329	0.3109	0.3257	0.094*
C23	−0.0313 (5)	0.3533 (2)	0.2233 (2)	0.0659 (9)
C24	−0.0729 (7)	0.3695 (3)	0.1519 (2)	0.0998 (14)
H24A	−0.1835	0.3473	0.1419	0.150*
H24B	0.0107	0.3434	0.1238	0.150*
H24C	−0.0727	0.4281	0.1438	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.120 (3)	0.0713 (16)	0.0813 (17)	0.0170 (17)	0.0044 (17)	−0.0217 (14)
O2	0.0476 (12)	0.0478 (11)	0.0594 (12)	0.0048 (10)	−0.0058 (10)	−0.0012 (9)
O3	0.0478 (15)	0.0655 (15)	0.146 (2)	0.0166 (12)	0.0075 (16)	0.0345 (16)
O4	0.0336 (13)	0.0779 (15)	0.114 (2)	−0.0037 (11)	−0.0066 (13)	0.0194 (14)
O5	0.073 (2)	0.103 (2)	0.134 (3)	0.0347 (17)	−0.0133 (19)	−0.0360 (19)
O6	0.0322 (13)	0.0753 (16)	0.130 (2)	0.0029 (12)	−0.0104 (15)	−0.0225 (16)
O7	0.0546 (14)	0.0652 (13)	0.0592 (13)	−0.0139 (11)	−0.0051 (11)	0.0106 (11)
O8	0.156 (3)	0.0725 (16)	0.0770 (17)	−0.0304 (19)	0.0162 (19)	0.0167 (14)
O9	0.0596 (16)	0.0959 (19)	0.0993 (19)	−0.0336 (14)	0.0093 (16)	−0.0269 (16)
O10	0.0552 (15)	0.0853 (17)	0.0808 (16)	−0.0177 (13)	0.0012 (13)	−0.0108 (13)
C1	0.131 (5)	0.113 (4)	0.120 (4)	−0.045 (4)	−0.039 (4)	0.056 (3)
C2	0.078 (3)	0.092 (3)	0.080 (3)	−0.021 (2)	−0.023 (2)	0.025 (2)
C3	0.096 (3)	0.139 (4)	0.062 (2)	−0.020 (3)	−0.006 (2)	0.031 (3)
C4	0.084 (3)	0.101 (3)	0.064 (2)	0.011 (3)	0.000 (2)	0.000 (2)
C5	0.0486 (19)	0.069 (2)	0.0539 (19)	−0.0014 (16)	−0.0107 (16)	0.0026 (15)
C6	0.058 (2)	0.0614 (18)	0.0583 (18)	−0.0005 (17)	−0.0094 (16)	−0.0020 (16)
C7	0.081 (3)	0.063 (2)	0.078 (3)	−0.006 (2)	−0.021 (2)	0.0089 (18)
C8	0.053 (2)	0.063 (2)	0.0590 (19)	0.0119 (17)	−0.0073 (16)	−0.0109 (17)
C9	0.0333 (15)	0.0432 (15)	0.072 (2)	0.0012 (13)	−0.0100 (15)	0.0000 (14)
C10	0.0381 (18)	0.0554 (18)	0.074 (2)	0.0012 (15)	−0.0046 (16)	0.0037 (16)
C11	0.0348 (15)	0.0463 (15)	0.074 (2)	−0.0050 (13)	−0.0067 (15)	0.0072 (15)
C12	0.0415 (17)	0.0513 (18)	0.084 (2)	−0.0003 (15)	−0.0005 (18)	0.0045 (17)
C13	0.056 (2)	0.063 (2)	0.063 (2)	0.0064 (17)	0.0110 (17)	0.0155 (17)
C14	0.0509 (19)	0.0625 (19)	0.0554 (19)	0.0101 (16)	−0.0023 (16)	0.0099 (15)
C15	0.090 (3)	0.072 (2)	0.066 (2)	0.001 (2)	0.015 (2)	0.0115 (18)
C16	0.114 (4)	0.078 (3)	0.062 (2)	0.011 (3)	0.003 (2)	0.002 (2)
C17	0.077 (3)	0.066 (2)	0.069 (2)	0.015 (2)	−0.025 (2)	0.0038 (18)
C18	0.093 (3)	0.077 (2)	0.077 (3)	−0.027 (2)	−0.020 (2)	0.018 (2)
C19	0.075 (3)	0.087 (3)	0.061 (2)	−0.022 (2)	−0.005 (2)	0.0113 (19)
C20	0.123 (4)	0.083 (3)	0.102 (3)	0.005 (3)	−0.042 (3)	−0.007 (2)
C21	0.093 (3)	0.082 (3)	0.100 (3)	−0.004 (2)	−0.019 (3)	−0.022 (2)
C22	0.063 (2)	0.076 (2)	0.096 (3)	−0.003 (2)	−0.016 (2)	−0.008 (2)
C23	0.055 (2)	0.0564 (18)	0.086 (3)	−0.0066 (17)	0.000 (2)	−0.0240 (18)
C24	0.106 (4)	0.103 (3)	0.090 (3)	0.007 (3)	−0.018 (3)	−0.017 (2)

Geometric parameters (Å, º)

O1—C8	1.198 (4)	C9—C10	1.522 (4)
O2—C8	1.353 (4)	C9—H9A	0.9800
O2—C9	1.419 (3)	C10—O3	1.296 (4)
O3—C10	1.296 (4)	C11—C12	1.512 (4)
O3—H3	0.96 (5)	C11—H11A	0.9800
O4—C10	1.187 (4)	C13—O8	1.196 (4)
O5—C12	1.184 (4)	C13—C14	1.469 (5)
O6—C12	1.320 (4)	C14—C15	1.376 (5)
O6—H6	0.82 (4)	C14—C19	1.377 (5)
O7—C13	1.341 (4)	C15—C16	1.356 (5)
O7—C11	1.428 (4)	C15—H15A	0.9300
O8—C13	1.196 (4)	C16—C17	1.382 (5)
O9—C23	1.209 (4)	C16—H16A	0.9300
O10—C23	1.304 (4)	C17—C18	1.380 (5)
O10—C22	1.457 (4)	C17—C20	1.503 (5)
C1—C2	1.513 (6)	C18—C19	1.370 (5)
C1—H1A	0.9600	C18—H18A	0.9300
C1—H1B	0.9600	C19—H19A	0.9300
C1—H1C	0.9600	C20—H20A	0.9600
C2—C7	1.368 (6)	C20—H20B	0.9600
C2—C3	1.379 (7)	C20—H20C	0.9600
C3—C4	1.370 (6)	C21—C22	1.469 (5)
C3—H3A	0.9300	C21—H21A	0.9600
C4—C5	1.387 (5)	C21—H21B	0.9600
C4—H4A	0.9300	C21—H21C	0.9600
C5—C6	1.382 (5)	C22—H22A	0.9700
C5—C8	1.469 (5)	C22—H22B	0.9700
C6—C7	1.378 (5)	C23—C24	1.486 (6)
C6—H6A	0.9300	C24—H24A	0.9600
C7—H7A	0.9300	C24—H24B	0.9600
C9—C11	1.503 (5)	C24—H24C	0.9600
C8—O2—C9	115.6 (2)	O6—C12—C11	110.3 (3)
C10—O3—H3	112 (2)	O8—C13—O7	121.7 (3)
C12—O6—H6	101 (3)	O8—C13—C14	125.7 (3)
C13—O7—C11	116.2 (2)	O7—C13—C14	112.6 (3)
C23—O10—C22	118.5 (3)	C15—C14—C19	117.8 (3)
C2—C1—H1A	109.5	C15—C14—C13	118.7 (3)
C2—C1—H1B	109.5	C19—C14—C13	123.4 (3)
H1A—C1—H1B	109.5	C16—C15—C14	121.2 (4)
C2—C1—H1C	109.5	C16—C15—H15A	119.4
H1A—C1—H1C	109.5	C14—C15—H15A	119.4
H1B—C1—H1C	109.5	C15—C16—C17	121.6 (4)
C7—C2—C3	117.9 (4)	C15—C16—H16A	119.2
C7—C2—C1	121.7 (5)	C17—C16—H16A	119.2
C3—C2—C1	120.3 (4)	C18—C17—C16	117.1 (4)
C4—C3—C2	121.4 (4)	C18—C17—C20	121.3 (4)
C4—C3—H3A	119.3	C16—C17—C20	121.6 (4)
C2—C3—H3A	119.3	C19—C18—C17	121.3 (4)
C3—C4—C5	120.1 (4)	C19—C18—H18A	119.3
C3—C4—H4A	120.0	C17—C18—H18A	119.3
C5—C4—H4A	120.0	C18—C19—C14	120.9 (3)
C6—C5—C4	119.1 (3)	C18—C19—H19A	119.5
C6—C5—C8	122.3 (3)	C14—C19—H19A	119.5
C4—C5—C8	118.6 (3)	C17—C20—H20A	109.5
C7—C6—C5	119.5 (3)	C17—C20—H20B	109.5
C7—C6—H6A	120.3	H20A—C20—H20B	109.5
C5—C6—H6A	120.3	C17—C20—H20C	109.5
C2—C7—C6	122.1 (4)	H20A—C20—H20C	109.5
C2—C7—H7A	119.0	H20B—C20—H20C	109.5
C6—C7—H7A	119.0	C22—C21—H21A	109.5
O1—C8—O2	121.3 (3)	C22—C21—H21B	109.5
O1—C8—C5	125.8 (3)	H21A—C21—H21B	109.5
O2—C8—C5	112.9 (3)	C22—C21—H21C	109.5
O2—C9—C11	107.7 (2)	H21A—C21—H21C	109.5
O2—C9—C10	111.1 (2)	H21B—C21—H21C	109.5
C11—C9—C10	111.1 (3)	O10—C22—C21	111.2 (3)
O2—C9—H9A	108.9	O10—C22—H22A	109.4
C11—C9—H9A	108.9	C21—C22—H22A	109.4
C10—C9—H9A	108.9	O10—C22—H22B	109.4
O4—C10—O3	126.2 (3)	C21—C22—H22B	109.4
O4—C10—C9	123.8 (3)	H22A—C22—H22B	108.0
O3—C10—C9	110.1 (3)	O9—C23—O10	122.1 (4)
O7—C11—C9	108.8 (2)	O9—C23—C24	124.8 (4)
O7—C11—C12	108.9 (3)	O10—C23—C24	113.1 (4)
C9—C11—C12	114.1 (3)	C23—C24—H24A	109.5
O7—C11—H11A	108.3	C23—C24—H24B	109.5
C9—C11—H11A	108.3	H24A—C24—H24B	109.5
C12—C11—H11A	108.3	C23—C24—H24C	109.5
O5—C12—O6	124.8 (3)	H24A—C24—H24C	109.5
O5—C12—C11	124.8 (3)	H24B—C24—H24C	109.5
C7—C2—C3—C4	−0.8 (7)	O2—C9—C11—C12	−63.2 (3)
C1—C2—C3—C4	177.2 (5)	C10—C9—C11—C12	174.8 (2)
C2—C3—C4—C5	−0.1 (7)	O7—C11—C12—O5	11.1 (5)
C3—C4—C5—C6	0.9 (6)	C9—C11—C12—O5	132.7 (4)
C3—C4—C5—C8	−178.9 (4)	O7—C11—C12—O6	−170.8 (3)
C4—C5—C6—C7	−0.7 (5)	C9—C11—C12—O6	−49.2 (3)
C8—C5—C6—C7	179.1 (3)	C11—O7—C13—O8	−7.7 (5)
C3—C2—C7—C6	1.1 (7)	C11—O7—C13—O8	−7.7 (5)
C1—C2—C7—C6	−177.0 (4)	C11—O7—C13—C14	170.5 (3)
C5—C6—C7—C2	−0.3 (6)	O8—C13—C14—C15	9.1 (6)
C9—O2—C8—O1	−3.0 (5)	O8—C13—C14—C15	9.1 (6)
C9—O2—C8—C5	177.9 (3)	O7—C13—C14—C15	−169.1 (3)
C6—C5—C8—O1	−171.1 (4)	O8—C13—C14—C19	−173.6 (4)
C4—C5—C8—O1	8.7 (6)	O8—C13—C14—C19	−173.6 (4)
C6—C5—C8—O2	7.9 (5)	O7—C13—C14—C19	8.2 (5)
C4—C5—C8—O2	−172.3 (3)	C19—C14—C15—C16	−1.1 (6)
C8—O2—C9—C11	164.8 (3)	C13—C14—C15—C16	176.4 (4)
C8—O2—C9—C10	−73.3 (3)	C14—C15—C16—C17	1.4 (7)
O2—C9—C10—O4	−3.1 (5)	C15—C16—C17—C18	−0.1 (7)
C11—C9—C10—O4	116.8 (4)	C15—C16—C17—C20	179.5 (4)
O2—C9—C10—O3	176.0 (3)	C16—C17—C18—C19	−1.5 (7)
C11—C9—C10—O3	−64.1 (3)	C20—C17—C18—C19	178.9 (4)
O2—C9—C10—O3	176.0 (3)	C17—C18—C19—C14	1.9 (7)
C11—C9—C10—O3	−64.1 (3)	C15—C14—C19—C18	−0.6 (6)
C13—O7—C11—C9	147.9 (3)	C13—C14—C19—C18	−177.9 (4)
C13—O7—C11—C12	−87.3 (3)	C23—O10—C22—C21	−81.1 (4)
O2—C9—C11—O7	58.5 (3)	C22—O10—C23—O9	−2.0 (5)
C10—C9—C11—O7	−63.5 (3)	C22—O10—C23—C24	178.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O9^i	0.96 (5)	1.63 (5)	2.585 (3)	173 (4)
O6—H6···O4^ii	0.82 (4)	1.92 (5)	2.697 (3)	159 (4)
C24—H24C···O5^iii	0.96	2.57	3.328 (5)	136
C11—H11A···O3	0.98	2.53	2.872 (4)	100
C11—H11A···O8	0.98	2.23	2.618 (4)	102

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