(2S)-[(2S)-2-Hydro­xy-2-phenyl­ethano­yl­oxy]­phenyl­acetic acid

The novel title compound, C₁₆H₁₄O₅, forms four intermol­ecular hydrogen bonds and takes part in two chains running along the shortest crystallographic b axis.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.098
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.92 Ratio

Alert level C
PLAT213_ALERT_2_C Atom C16     has ADP max/min Ratio .............       3.10 prolat
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.83 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C15
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C13
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           27.34
           From the CIF: _reflns_number_total               1760
           Count of symmetry unique reflns         1786
           Completeness (_total/calc)             98.54%
           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
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CERIUS² (Accelrys, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C16H14O5	F(000) = 300
Mr = 286.27	Dx = 1.317 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4075 reflections
a = 10.5196 (4) Å	θ = 1.0–27.5°
b = 6.4129 (3) Å	µ = 0.10 mm^−1
c = 11.7201 (7) Å	T = 150 K
β = 114.107 (2)°	Needles, colourless
V = 721.69 (6) Å^3	0.3 × 0.15 × 0.1 mm
Z = 2

Data collection

KappaCCD diffractometer	1760 independent reflections
Radiation source: Enraf Nonius FR590	1413 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
CCD rotation images, thick slices scans	θmax = 27.3°, θmin = 3.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −11→13
Tmin = 0.916, Tmax = 0.990	k = −7→8
4184 measured reflections	l = −12→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difamp
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0442P)^2 + 0.1103P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1760 reflections	Δρmax = 0.20 e Å^−3
193 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.115 (14)

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	0.1660 (3)	0.8701 (4)	0.0327 (2)	0.0286 (5)
C2	0.3125 (3)	0.7920 (4)	0.0599 (2)	0.0296 (5)
H2	0.3782	0.909	0.0833	0.035*
C3	0.3165 (2)	0.6790 (4)	−0.0517 (2)	0.0288 (5)
C4	0.3786 (3)	0.7720 (4)	−0.1229 (3)	0.0377 (6)
H4	0.4203	0.9024	−0.101	0.045*
C5	0.3780 (3)	0.6688 (5)	−0.2269 (3)	0.0469 (7)
H5	0.4186	0.7316	−0.2754	0.056*
C6	0.3185 (3)	0.4751 (5)	−0.2597 (2)	0.0429 (7)
H6	0.3181	0.4079	−0.3302	0.051*
C7	0.2593 (3)	0.3809 (5)	−0.1873 (2)	0.0413 (7)
H7	0.2208	0.2483	−0.2077	0.05*
C8	0.2573 (3)	0.4840 (4)	−0.0841 (2)	0.0351 (6)
H8	0.2157	0.4213	−0.0364	0.042*
C11	0.3771 (3)	0.7273 (4)	0.2742 (2)	0.0315 (6)
C12	0.3946 (3)	0.5596 (4)	0.3701 (2)	0.0338 (6)
H12	0.4399	0.4374	0.3528	0.041*
C13	0.2518 (3)	0.4995 (4)	0.3619 (2)	0.0342 (6)
C14	0.1924 (4)	0.3124 (5)	0.3093 (3)	0.0668 (11)
H14	0.2399	0.2227	0.278	0.08*
C15	0.0637 (5)	0.2576 (8)	0.3026 (5)	0.111 (2)
H15	0.0254	0.1299	0.2678	0.133*
C16	−0.0080 (5)	0.3859 (12)	0.3455 (4)	0.111 (2)
H16	−0.096	0.3481	0.3392	0.134*
C17	0.0495 (4)	0.5730 (10)	0.3988 (3)	0.0881 (18)
H17	0.001	0.6612	0.4299	0.106*
C18	0.1797 (3)	0.6309 (6)	0.4063 (2)	0.0535 (8)
H18	0.218	0.7585	0.4413	0.064*
O1	0.1407 (2)	1.0446 (3)	−0.03237 (18)	0.0400 (5)
H1	0.0615	1.0845	−0.047	0.06*
O2	0.08478 (19)	0.7830 (3)	0.06471 (17)	0.0404 (5)
O3	0.35120 (18)	0.6433 (3)	0.16153 (14)	0.0351 (4)
O12	0.38098 (19)	0.9121 (3)	0.29324 (16)	0.0365 (5)
O13	0.4817 (2)	0.6462 (3)	0.48698 (17)	0.0441 (5)
H13	0.5145	0.5523	0.5382	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0333 (13)	0.0256 (13)	0.0240 (11)	−0.0043 (10)	0.0088 (10)	−0.0027 (9)
C2	0.0320 (13)	0.0231 (12)	0.0292 (12)	−0.0007 (10)	0.0079 (10)	0.0017 (10)
C3	0.0258 (12)	0.0294 (13)	0.0281 (12)	0.0041 (10)	0.0078 (10)	0.0038 (11)
C4	0.0326 (14)	0.0384 (15)	0.0444 (15)	0.0015 (12)	0.0179 (12)	0.0047 (12)
C5	0.0471 (17)	0.0562 (19)	0.0464 (16)	0.0053 (16)	0.0284 (14)	0.0089 (16)
C6	0.0438 (16)	0.0533 (18)	0.0335 (14)	0.0143 (14)	0.0179 (13)	0.0009 (13)
C7	0.0477 (17)	0.0372 (15)	0.0364 (15)	0.0009 (13)	0.0144 (13)	−0.0039 (12)
C8	0.0403 (15)	0.0320 (13)	0.0329 (12)	−0.0023 (12)	0.0148 (11)	0.0012 (11)
C11	0.0274 (13)	0.0350 (14)	0.0297 (13)	0.0020 (10)	0.0091 (11)	−0.0019 (10)
C12	0.0357 (14)	0.0333 (13)	0.0257 (12)	0.0052 (11)	0.0057 (11)	−0.0008 (10)
C13	0.0346 (13)	0.0353 (14)	0.0244 (12)	0.0020 (11)	0.0034 (10)	0.0073 (11)
C14	0.0483 (19)	0.0374 (17)	0.078 (2)	−0.0012 (15)	−0.0113 (17)	0.0060 (17)
C15	0.050 (3)	0.075 (3)	0.140 (5)	−0.028 (2)	−0.030 (3)	0.053 (3)
C16	0.034 (2)	0.183 (6)	0.085 (3)	−0.026 (3)	−0.009 (2)	0.080 (4)
C17	0.041 (2)	0.185 (6)	0.0367 (18)	0.010 (3)	0.0152 (16)	0.019 (2)
C18	0.0411 (16)	0.084 (2)	0.0310 (14)	0.0032 (17)	0.0105 (13)	−0.0048 (16)
O1	0.0391 (11)	0.0309 (10)	0.0538 (12)	0.0078 (8)	0.0227 (10)	0.0119 (9)
O2	0.0369 (10)	0.0417 (11)	0.0431 (11)	−0.0066 (9)	0.0167 (9)	0.0042 (9)
O3	0.0448 (11)	0.0314 (9)	0.0250 (9)	0.0053 (9)	0.0101 (8)	0.0021 (8)
O12	0.0451 (11)	0.0307 (10)	0.0311 (9)	−0.0014 (8)	0.0129 (8)	−0.0022 (8)
O13	0.0431 (11)	0.0440 (11)	0.0289 (9)	−0.0041 (9)	−0.0019 (8)	0.0054 (9)

Geometric parameters (Å, º)

C1—O2	1.202 (3)	C11—O3	1.347 (3)
C1—O1	1.319 (3)	C11—C12	1.511 (4)
C1—C2	1.525 (3)	C12—O13	1.414 (3)
C2—O3	1.449 (3)	C12—C13	1.515 (4)
C2—C3	1.511 (3)	C12—H12	0.98
C2—H2	0.98	C13—C18	1.370 (4)
C3—C8	1.380 (4)	C13—C14	1.377 (4)
C3—C4	1.388 (3)	C14—C15	1.369 (6)
C4—C5	1.385 (4)	C14—H14	0.93
C4—H4	0.93	C15—C16	1.345 (8)
C5—C6	1.373 (5)	C15—H15	0.93
C5—H5	0.93	C16—C17	1.374 (9)
C6—C7	1.380 (4)	C16—H16	0.93
C6—H6	0.93	C17—C18	1.387 (5)
C7—C8	1.386 (4)	C17—H17	0.93
C7—H7	0.93	C18—H18	0.93
C8—H8	0.93	O1—H1	0.82
C11—O12	1.203 (3)	O13—H13	0.82
O2—C1—O1	125.0 (2)	O3—C11—C12	111.0 (2)
O2—C1—C2	124.6 (2)	O13—C12—C11	105.9 (2)
O1—C1—C2	110.3 (2)	O13—C12—C13	113.2 (2)
O3—C2—C3	107.35 (19)	C11—C12—C13	108.5 (2)
O3—C2—C1	107.97 (19)	O13—C12—H12	109.7
C3—C2—C1	111.07 (19)	C11—C12—H12	109.7
O3—C2—H2	110.1	C13—C12—H12	109.7
C3—C2—H2	110.1	C18—C13—C14	119.1 (3)
C1—C2—H2	110.1	C18—C13—C12	120.5 (3)
C8—C3—C4	119.7 (2)	C14—C13—C12	120.4 (3)
C8—C3—C2	120.3 (2)	C15—C14—C13	120.4 (4)
C4—C3—C2	120.0 (2)	C15—C14—H14	119.8
C5—C4—C3	119.3 (3)	C13—C14—H14	119.8
C5—C4—H4	120.3	C16—C15—C14	120.9 (5)
C3—C4—H4	120.3	C16—C15—H15	119.5
C6—C5—C4	121.1 (3)	C14—C15—H15	119.5
C6—C5—H5	119.5	C15—C16—C17	119.6 (4)
C4—C5—H5	119.5	C15—C16—H16	120.2
C5—C6—C7	119.5 (3)	C17—C16—H16	120.2
C5—C6—H6	120.2	C16—C17—C18	120.2 (5)
C7—C6—H6	120.2	C16—C17—H17	119.9
C6—C7—C8	120.0 (3)	C18—C17—H17	119.9
C6—C7—H7	120	C13—C18—C17	119.8 (4)
C8—C7—H7	120	C13—C18—H18	120.1
C3—C8—C7	120.4 (2)	C17—C18—H18	120.1
C3—C8—H8	119.8	C1—O1—H1	109.5
C7—C8—H8	119.8	C11—O3—C2	114.8 (2)
O12—C11—O3	123.6 (2)	C12—O13—H13	109.5
O12—C11—C12	125.4 (2)
O2—C1—C2—O3	−18.6 (3)	O12—C11—C12—C13	92.7 (3)
O1—C1—C2—O3	162.27 (19)	O3—C11—C12—C13	−85.1 (2)
O2—C1—C2—C3	98.8 (3)	O13—C12—C13—C18	44.0 (3)
O1—C1—C2—C3	−80.3 (2)	C11—C12—C13—C18	−73.3 (3)
O3—C2—C3—C8	45.5 (3)	O13—C12—C13—C14	−136.3 (3)
C1—C2—C3—C8	−72.3 (3)	C11—C12—C13—C14	106.4 (3)
O3—C2—C3—C4	−135.1 (2)	C18—C13—C14—C15	−0.7 (5)
C1—C2—C3—C4	107.1 (2)	C12—C13—C14—C15	179.6 (3)
C8—C3—C4—C5	1.1 (4)	C13—C14—C15—C16	0.9 (6)
C2—C3—C4—C5	−178.2 (2)	C14—C15—C16—C17	−1.1 (7)
C3—C4—C5—C6	−0.8 (4)	C15—C16—C17—C18	1.1 (6)
C4—C5—C6—C7	−0.5 (4)	C14—C13—C18—C17	0.7 (4)
C5—C6—C7—C8	1.6 (4)	C12—C13—C18—C17	−179.6 (3)
C4—C3—C8—C7	−0.1 (4)	C16—C17—C18—C13	−0.9 (5)
C2—C3—C8—C7	179.2 (2)	O12—C11—O3—C2	−6.6 (3)
C6—C7—C8—C3	−1.2 (4)	C12—C11—O3—C2	171.2 (2)
O12—C11—C12—O13	−29.2 (4)	C3—C2—O3—C11	168.6 (2)
O3—C11—C12—O13	153.0 (2)	C1—C2—O3—C11	−71.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.94	2.715 (3)	157
O13—H13···O12^ii	0.82	2.04	2.817 (3)	159

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