(2S,3S)-Diethyl 2,3-O-benzyl­idenetartrate

The asymmetric unit of the title compound, C₁₅H₁₈O₆, contains two crystallographically independent mol­ecules. There are intramolecular and intermolecular C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.066
• wR factor = 0.150
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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           26.99
           From the CIF: _reflns_number_total               3323
           Count of symmetry unique reflns         3329
           Completeness (_total/calc)             99.82%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24    = .          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Diethyl 2,3-O-benzylidene-D-tartarate

Crystal data

C15H18O6	F(000) = 624
Mr = 294.29	Dx = 1.310 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 7.5400 (15) Å	θ = 9–12°
b = 26.500 (5) Å	µ = 0.10 mm^−1
c = 8.2100 (16) Å	T = 291 K
β = 114.50 (3)°	Block, colourless
V = 1492.7 (6) Å^3	0.30 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3323 independent reflections
Radiation source: sealed tube	2549 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→9
Tmin = 0.97, Tmax = 0.97	k = −22→33
8736 measured reflections	l = −10→10

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.99P] where P = (Fo^2 + 2Fc^2)/3
3323 reflections	(Δ/σ)max < 0.001
384 parameters	Δρmax = 0.22 e Å^−3
1 restraint	Δρmin = −0.22 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
C1	1.1727 (9)	0.8725 (3)	0.2846 (8)	0.0476 (15)
C2	1.2078 (10)	0.8236 (3)	0.2463 (10)	0.0588 (18)
H2	1.1083	0.8049	0.1606	0.071*
C3	1.3215 (9)	0.9006 (3)	0.4137 (9)	0.0525 (16)
H3	1.2977	0.9334	0.4391	0.063*
C4	1.5069 (10)	0.8793 (3)	0.5049 (9)	0.0494 (14)
H4	1.6074	0.8975	0.5914	0.059*
C5	1.5359 (9)	0.8301 (2)	0.4621 (8)	0.0450 (13)
H5	1.6580	0.8154	0.5214	0.054*
C6	1.3898 (9)	0.8026 (3)	0.3352 (9)	0.0563 (17)
H6	1.4137	0.7699	0.3091	0.068*
C7	0.9717 (9)	0.8899 (2)	0.1815 (8)	0.0450 (13)
H7	0.9106	0.8651	0.0859	0.054*
C8	0.7349 (8)	0.9511 (2)	0.0707 (7)	0.0386 (12)
H8	0.6446	0.9518	−0.0562	0.046*
C9	0.6764 (8)	0.9106 (2)	0.1749 (8)	0.0424 (13)
H9	0.5984	0.9232	0.2366	0.051*
C10	0.7397 (9)	1.0013 (2)	0.1624 (8)	0.0443 (14)
C11	0.5422 (8)	1.0611 (2)	0.2281 (7)	0.0406 (12)
H11A	0.5443	1.0888	0.1517	0.049*
H11B	0.6462	1.0659	0.3462	0.049*
C12	0.3415 (8)	1.0580 (2)	0.2387 (8)	0.0453 (14)
H12A	0.2841	1.0255	0.1972	0.068*
H12B	0.2572	1.0839	0.1650	0.068*
H12C	0.3593	1.0627	0.3605	0.068*
C13	0.5855 (8)	0.8668 (2)	0.0464 (7)	0.0388 (12)
C14	0.2761 (9)	0.8399 (2)	−0.1768 (8)	0.0456 (14)
H14A	0.2960	0.8079	−0.1144	0.055*
H14B	0.3141	0.8359	−0.2754	0.055*
C15	0.0596 (9)	0.8546 (2)	−0.2501 (8)	0.0442 (14)
H15A	0.0318	0.8685	−0.1553	0.066*
H15B	−0.0194	0.8252	−0.2975	0.066*
H15C	0.0313	0.8792	−0.3433	0.066*
C16	0.7141 (9)	0.6673 (2)	0.3514 (7)	0.0415 (13)
C17	0.8833 (8)	0.6460 (2)	0.4815 (7)	0.0423 (13)
H17	0.8824	0.6127	0.5172	0.051*
C18	1.0524 (8)	0.6744 (2)	0.5572 (7)	0.0380 (12)
H18	1.1643	0.6603	0.6447	0.046*
C19	1.0549 (9)	0.7244 (2)	0.5020 (7)	0.0402 (12)
H19	1.1689	0.7433	0.5513	0.048*
C20	0.8859 (8)	0.7456 (2)	0.3729 (7)	0.0396 (12)
H20	0.8867	0.7788	0.3364	0.048*
C21	0.7154 (9)	0.7169 (2)	0.2984 (8)	0.0424 (13)
H21	0.6024	0.7312	0.2130	0.051*
C22	0.5514 (9)	0.6315 (2)	0.2710 (7)	0.0421 (13)
H22	0.5994	0.5968	0.2804	0.051*
C23	0.2238 (9)	0.6249 (2)	0.2336 (7)	0.0404 (12)
H23	0.1270	0.6434	0.2611	0.049*
C24	0.2236 (8)	0.6414 (2)	0.0559 (6)	0.0346 (11)
H24	0.1570	0.6159	−0.0352	0.041*
C25	0.2039 (8)	0.5683 (2)	0.2466 (7)	0.0389 (12)
C26	−0.0143 (9)	0.5029 (2)	0.2321 (9)	0.0473 (14)
H26A	0.0906	0.4868	0.3319	0.057*
H26B	−0.0273	0.4866	0.1219	0.057*
C27	−0.2038 (9)	0.5002 (2)	0.2544 (8)	0.0411 (12)
H27A	−0.1940	0.5207	0.3541	0.062*
H27B	−0.2288	0.4659	0.2757	0.062*
H27C	−0.3085	0.5123	0.1475	0.062*
C28	0.1201 (9)	0.6911 (2)	−0.0020 (7)	0.0389 (12)
C29	−0.1877 (8)	0.7302 (2)	−0.1310 (7)	0.0360 (11)
H29A	−0.1631	0.7481	−0.2227	0.043*
H29B	−0.1617	0.7524	−0.0296	0.043*
C30	−0.3949 (8)	0.7086 (2)	−0.2038 (8)	0.0423 (13)
H30A	−0.4374	0.7007	−0.3284	0.063*
H30B	−0.4813	0.7331	−0.1896	0.063*
H30C	−0.3956	0.6786	−0.1389	0.063*
O1	0.9301 (6)	0.93990 (15)	0.0945 (5)	0.0440 (10)
O2	0.8604 (6)	0.88909 (15)	0.2893 (5)	0.0434 (10)
O3	0.8785 (5)	1.02980 (16)	0.2151 (5)	0.0431 (9)
O4	0.5637 (6)	1.01352 (14)	0.1536 (5)	0.0425 (9)
O5	0.6363 (5)	0.82564 (14)	0.0246 (5)	0.0387 (9)
O6	0.3962 (6)	0.87824 (15)	−0.0556 (5)	0.0407 (9)
O7	0.4201 (6)	0.63674 (16)	0.3578 (5)	0.0485 (10)
O8	0.4236 (6)	0.64430 (15)	0.0836 (5)	0.0399 (9)
O9	0.3241 (6)	0.53567 (17)	0.2538 (5)	0.0487 (10)
O10	0.0227 (6)	0.55682 (15)	0.2270 (5)	0.0409 (9)
O11	0.1993 (6)	0.73071 (17)	0.0087 (5)	0.0483 (10)
O12	−0.0752 (5)	0.68353 (13)	−0.0778 (5)	0.0367 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.048 (4)	0.055 (4)	0.039 (3)	0.011 (3)	0.017 (3)	0.012 (3)
C2	0.045 (4)	0.062 (4)	0.067 (4)	0.006 (3)	0.021 (3)	0.033 (4)
C3	0.047 (3)	0.058 (4)	0.053 (4)	0.004 (3)	0.021 (3)	0.022 (3)
C4	0.056 (4)	0.052 (4)	0.045 (3)	0.002 (3)	0.026 (3)	0.021 (3)
C5	0.046 (3)	0.048 (3)	0.037 (3)	−0.001 (3)	0.012 (3)	0.002 (3)
C6	0.042 (3)	0.055 (4)	0.050 (4)	0.000 (3)	−0.003 (3)	0.002 (3)
C7	0.043 (3)	0.040 (3)	0.044 (3)	−0.001 (2)	0.010 (3)	0.013 (2)
C8	0.038 (3)	0.037 (3)	0.036 (3)	−0.001 (2)	0.011 (2)	0.019 (2)
C9	0.036 (3)	0.040 (3)	0.040 (3)	0.002 (2)	0.005 (2)	0.021 (2)
C10	0.037 (3)	0.044 (3)	0.043 (3)	−0.010 (2)	0.008 (3)	0.005 (2)
C11	0.040 (3)	0.045 (3)	0.035 (3)	−0.013 (2)	0.014 (2)	−0.003 (2)
C12	0.045 (3)	0.037 (3)	0.048 (3)	0.015 (2)	0.013 (3)	−0.007 (3)
C13	0.035 (3)	0.036 (3)	0.040 (3)	0.012 (2)	0.009 (2)	0.010 (2)
C14	0.050 (4)	0.035 (3)	0.044 (3)	0.003 (2)	0.010 (3)	0.001 (2)
C15	0.046 (3)	0.041 (3)	0.044 (3)	0.006 (2)	0.016 (3)	−0.016 (3)
C16	0.045 (3)	0.041 (3)	0.034 (3)	0.002 (2)	0.012 (2)	0.001 (2)
C17	0.040 (3)	0.042 (3)	0.040 (3)	−0.004 (2)	0.011 (2)	−0.003 (2)
C18	0.043 (3)	0.035 (3)	0.043 (3)	0.011 (2)	0.025 (3)	−0.002 (2)
C19	0.046 (3)	0.035 (3)	0.043 (3)	−0.001 (2)	0.021 (3)	−0.004 (2)
C20	0.040 (3)	0.038 (3)	0.041 (3)	−0.004 (2)	0.017 (2)	0.010 (2)
C21	0.047 (3)	0.032 (3)	0.043 (3)	0.000 (2)	0.013 (3)	0.005 (2)
C22	0.051 (3)	0.029 (3)	0.039 (3)	0.004 (2)	0.012 (2)	−0.001 (2)
C23	0.048 (3)	0.041 (3)	0.030 (2)	−0.012 (3)	0.014 (2)	−0.001 (2)
C24	0.040 (3)	0.040 (3)	0.027 (2)	−0.010 (2)	0.017 (2)	−0.013 (2)
C25	0.043 (3)	0.041 (3)	0.031 (3)	−0.011 (2)	0.014 (2)	−0.004 (2)
C26	0.045 (3)	0.038 (3)	0.049 (3)	−0.007 (2)	0.010 (3)	−0.004 (3)
C27	0.052 (3)	0.028 (3)	0.044 (3)	−0.009 (2)	0.020 (3)	0.001 (2)
C28	0.049 (3)	0.038 (3)	0.031 (3)	−0.009 (3)	0.019 (2)	−0.011 (2)
C29	0.041 (3)	0.030 (3)	0.032 (2)	−0.002 (2)	0.011 (2)	0.001 (2)
C30	0.033 (3)	0.045 (3)	0.038 (3)	−0.009 (2)	0.004 (2)	−0.008 (2)
O1	0.043 (2)	0.043 (2)	0.044 (2)	0.0114 (18)	0.0151 (19)	0.0179 (17)
O2	0.038 (2)	0.047 (2)	0.040 (2)	−0.0088 (17)	0.0111 (17)	0.0236 (17)
O3	0.038 (2)	0.047 (2)	0.043 (2)	−0.0176 (18)	0.0151 (17)	0.0104 (18)
O4	0.049 (2)	0.038 (2)	0.040 (2)	−0.0159 (17)	0.0186 (18)	−0.0082 (17)
O5	0.038 (2)	0.036 (2)	0.042 (2)	0.0146 (17)	0.0158 (17)	0.0115 (17)
O6	0.045 (2)	0.040 (2)	0.0380 (19)	0.0024 (17)	0.0180 (17)	0.0023 (17)
O7	0.054 (2)	0.045 (2)	0.043 (2)	−0.0064 (19)	0.0166 (19)	0.0075 (19)
O8	0.046 (2)	0.039 (2)	0.0300 (17)	−0.0108 (17)	0.0113 (16)	−0.0023 (16)
O9	0.052 (2)	0.053 (3)	0.043 (2)	0.007 (2)	0.0207 (19)	−0.0037 (19)
O10	0.044 (2)	0.042 (2)	0.0349 (18)	−0.0144 (17)	0.0143 (17)	−0.0084 (17)
O11	0.042 (2)	0.057 (3)	0.043 (2)	−0.015 (2)	0.0153 (18)	0.0066 (19)
O12	0.042 (2)	0.032 (2)	0.0347 (18)	−0.0050 (16)	0.0143 (16)	−0.0022 (15)

Geometric parameters (Å, º)

C1—C2	1.383 (10)	C16—C21	1.386 (8)
C1—C3	1.397 (10)	C16—C17	1.400 (8)
C1—C7	1.471 (8)	C16—C22	1.473 (8)
C2—C6	1.377 (9)	C17—C18	1.387 (8)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.402 (9)	C18—C19	1.402 (8)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.391 (10)	C19—C20	1.394 (8)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.369 (9)	C20—C21	1.398 (8)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—O2	1.450 (7)	C22—O7	1.446 (7)
C7—O1	1.476 (7)	C22—O8	1.476 (7)
C7—H7	0.9800	C22—H22	0.9800
C8—O1	1.434 (7)	C23—O7	1.441 (7)
C8—C10	1.522 (9)	C23—C25	1.517 (8)
C8—C9	1.545 (7)	C23—C24	1.522 (7)
C8—H8	0.9800	C23—H23	0.9800
C9—O2	1.432 (6)	C24—O8	1.431 (6)
C9—C13	1.528 (9)	C24—C28	1.502 (8)
C9—H9	0.9800	C24—H24	0.9800
C10—O3	1.216 (7)	C25—O9	1.236 (7)
C10—O4	1.339 (7)	C25—O10	1.343 (7)
C11—O4	1.439 (7)	C26—O10	1.460 (7)
C11—C12	1.554 (8)	C26—C27	1.516 (9)
C11—H11A	0.9700	C26—H26A	0.9700
C11—H11B	0.9700	C26—H26B	0.9700
C12—H12A	0.9600	C27—H27A	0.9600
C12—H12B	0.9600	C27—H27B	0.9600
C12—H12C	0.9600	C27—H27C	0.9600
C13—O5	1.193 (6)	C28—O11	1.194 (7)
C13—O6	1.356 (6)	C28—O12	1.354 (7)
C14—O6	1.447 (7)	C29—O12	1.461 (6)
C14—C15	1.537 (9)	C29—C30	1.534 (7)
C14—H14A	0.9700	C29—H29A	0.9700
C14—H14B	0.9700	C29—H29B	0.9700
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600
C2—C1—C3	120.2 (6)	C18—C17—H17	120.0
C2—C1—C7	114.3 (6)	C16—C17—H17	120.0
C3—C1—C7	125.5 (6)	C17—C18—C19	120.1 (6)
C6—C2—C1	120.0 (7)	C17—C18—H18	119.9
C6—C2—H2	120.0	C19—C18—H18	119.9
C1—C2—H2	120.0	C20—C19—C18	119.8 (5)
C1—C3—C4	120.0 (7)	C20—C19—H19	120.1
C1—C3—H3	120.0	C18—C19—H19	120.1
C4—C3—H3	120.0	C19—C20—C21	119.9 (5)
C5—C4—C3	118.0 (7)	C19—C20—H20	120.1
C5—C4—H4	121.0	C21—C20—H20	120.1
C3—C4—H4	121.0	C16—C21—C20	120.2 (6)
C6—C5—C4	121.9 (6)	C16—C21—H21	119.9
C6—C5—H5	119.0	C20—C21—H21	119.9
C4—C5—H5	119.0	O7—C22—C16	109.3 (4)
C5—C6—C2	120.0 (7)	O7—C22—O8	102.0 (4)
C5—C6—H6	120.0	C16—C22—O8	112.5 (4)
C2—C6—H6	120.0	O7—C22—H22	110.9
O2—C7—C1	111.3 (5)	C16—C22—H22	110.9
O2—C7—O1	104.4 (5)	O8—C22—H22	110.9
C1—C7—O1	121.4 (5)	O7—C23—C25	105.5 (5)
O2—C7—H7	106.3	O7—C23—C24	102.0 (4)
C1—C7—H7	106.3	C25—C23—C24	113.1 (5)
O1—C7—H7	106.3	O7—C23—H23	111.9
O1—C8—C10	107.5 (4)	C25—C23—H23	111.9
O1—C8—C9	107.1 (4)	C24—C23—H23	111.9
C10—C8—C9	106.6 (5)	O8—C24—C28	112.3 (4)
O1—C8—H8	111.8	O8—C24—C23	106.3 (4)
C10—C8—H8	111.8	C28—C24—C23	110.5 (4)
C9—C8—H8	111.8	O8—C24—H24	109.2
O2—C9—C13	100.7 (4)	C28—C24—H24	109.2
O2—C9—C8	102.6 (4)	C23—C24—H24	109.2
C13—C9—C8	107.1 (5)	O9—C25—O10	122.5 (5)
O2—C9—H9	114.9	O9—C25—C23	127.1 (5)
C13—C9—H9	114.9	O10—C25—C23	109.9 (5)
C8—C9—H9	114.9	O10—C26—C27	104.5 (5)
O3—C10—O4	123.8 (6)	O10—C26—H26A	110.9
O3—C10—C8	124.0 (6)	C27—C26—H26A	110.9
O4—C10—C8	111.5 (5)	O10—C26—H26B	110.9
O4—C11—C12	105.2 (4)	C27—C26—H26B	110.9
O4—C11—H11A	110.7	H26A—C26—H26B	108.9
C12—C11—H11A	110.7	C26—C27—H27A	109.5
O4—C11—H11B	110.7	C26—C27—H27B	109.5
C12—C11—H11B	110.7	H27A—C27—H27B	109.5
H11A—C11—H11B	108.8	C26—C27—H27C	109.5
C11—C12—H12A	109.5	H27A—C27—H27C	109.5
C11—C12—H12B	109.5	H27B—C27—H27C	109.5
H12A—C12—H12B	109.5	O11—C28—O12	125.4 (6)
C11—C12—H12C	109.5	O11—C28—C24	124.7 (5)
H12A—C12—H12C	109.5	O12—C28—C24	109.8 (4)
H12B—C12—H12C	109.5	O12—C29—C30	99.9 (4)
O5—C13—O6	115.7 (5)	O12—C29—H29A	111.8
O5—C13—C9	135.9 (5)	C30—C29—H29A	111.8
O6—C13—C9	108.2 (4)	O12—C29—H29B	111.8
O6—C14—C15	110.6 (5)	C30—C29—H29B	111.8
O6—C14—H14A	109.5	H29A—C29—H29B	109.5
C15—C14—H14A	109.5	C29—C30—H30A	109.5
O6—C14—H14B	109.5	C29—C30—H30B	109.5
C15—C14—H14B	109.5	H30A—C30—H30B	109.5
H14A—C14—H14B	108.1	C29—C30—H30C	109.5
C14—C15—H15A	109.5	H30A—C30—H30C	109.5
C14—C15—H15B	109.5	H30B—C30—H30C	109.5
H15A—C15—H15B	109.5	C8—O1—C7	104.5 (4)
C14—C15—H15C	109.5	C9—O2—C7	104.0 (4)
H15A—C15—H15C	109.5	C10—O4—C11	118.2 (4)
H15B—C15—H15C	109.5	C13—O6—C14	117.7 (4)
C21—C16—C17	120.0 (6)	C23—O7—C22	110.0 (4)
C21—C16—C22	125.7 (5)	C24—O8—C22	110.0 (4)
C17—C16—C22	114.1 (5)	C25—O10—C26	114.5 (5)
C18—C17—C16	120.0 (6)	C28—O12—C29	113.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O9	0.98	2.57	3.035 (7)	109
C14—H14A···O11	0.97	2.52	3.430 (7)	156
C7—H7···O5	0.98	2.18	2.873 (7)	126