2-Benz­yloxy-2-hydr­oxy-1-phenyl­ethanone

The stable title hemiacetal, C₁₅H₁₄O₃, has been prepared. One attractive feature in the structure is the gauche conformation determined by stereoelectronic factors. A hydrogen bond is formed between two neighbouring mol­ecules, in which the hydroxyl group acts as both donor and acceptor.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.126
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       6.57 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C10    -C15           1.37 Ang.

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

2-benzyloxy-2-hydroxy-1-phenylethanone

Crystal data

C15H14O3	F(000) = 512
Mr = 242.26	Dx = 1.254 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1709 reflections
a = 12.019 (3) Å	θ = 3.0–23.9°
b = 5.6824 (13) Å	µ = 0.09 mm^−1
c = 19.049 (4) Å	T = 294 K
β = 99.439 (4)°	Block, white
V = 1283.4 (5) Å^3	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2609 independent reflections
Radiation source: fine-focus sealed tube	1488 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→15
Tmin = 0.978, Tmax = 0.983	k = −7→7
6834 measured reflections	l = −23→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.1183P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2609 reflections	Δρmax = 0.14 e Å^−3
165 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (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 > 2σ(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	0.54684 (12)	−0.3476 (2)	0.63951 (7)	0.0736 (4)
O2	0.53160 (12)	−0.0465 (2)	0.73940 (7)	0.0739 (5)
H2	0.5121	0.0680	0.7606	0.111*
O3	0.71108 (9)	0.0378 (2)	0.71723 (6)	0.0597 (4)
C1	0.61786 (15)	−0.2672 (3)	0.51023 (10)	0.0577 (5)
H1	0.5804	−0.4071	0.5163	0.069*
C2	0.65741 (18)	−0.2272 (4)	0.44735 (11)	0.0712 (6)
H2A	0.6451	−0.3375	0.4108	0.085*
C3	0.71496 (19)	−0.0241 (4)	0.43897 (11)	0.0761 (6)
H3	0.7433	0.0017	0.3970	0.091*
C4	0.73104 (19)	0.1412 (4)	0.49185 (11)	0.0758 (6)
H4	0.7700	0.2790	0.4856	0.091*
C5	0.68957 (15)	0.1041 (3)	0.55451 (10)	0.0598 (5)
H5	0.6997	0.2181	0.5900	0.072*
C6	0.63301 (13)	−0.1025 (3)	0.56457 (8)	0.0450 (4)
C7	0.58837 (14)	−0.1570 (3)	0.63097 (9)	0.0488 (4)
C8	0.59593 (13)	0.0281 (3)	0.68918 (9)	0.0491 (4)
H8	0.5693	0.1808	0.6692	0.059*
C9	0.74335 (18)	0.2435 (4)	0.75800 (12)	0.0821 (7)
H9A	0.6872	0.2790	0.7877	0.098*
H9B	0.7475	0.3759	0.7264	0.098*
C10	0.85583 (15)	0.2070 (3)	0.80388 (9)	0.0546 (5)
C11	0.87571 (18)	0.0169 (4)	0.84761 (12)	0.0748 (6)
H11	0.8199	−0.0967	0.8473	0.090*
C12	0.9777 (2)	−0.0096 (5)	0.89241 (13)	0.0945 (8)
H12	0.9904	−0.1398	0.9223	0.113*
C13	1.0596 (2)	0.1564 (5)	0.89250 (14)	0.0982 (8)
H13	1.1278	0.1410	0.9232	0.118*
C14	1.04214 (19)	0.3426 (5)	0.84840 (14)	0.0920 (8)
H14	1.0989	0.4534	0.8477	0.110*
C15	0.94016 (18)	0.3684 (4)	0.80432 (11)	0.0719 (6)
H15	0.9284	0.4982	0.7743	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0964 (10)	0.0589 (9)	0.0705 (9)	−0.0246 (8)	0.0285 (8)	−0.0072 (7)
O2	0.0831 (10)	0.0706 (9)	0.0785 (10)	−0.0080 (8)	0.0444 (8)	−0.0122 (8)
O3	0.0472 (8)	0.0668 (9)	0.0627 (8)	0.0021 (6)	0.0022 (6)	−0.0211 (7)
C1	0.0548 (11)	0.0586 (12)	0.0590 (11)	−0.0036 (9)	0.0070 (9)	−0.0092 (10)
C2	0.0804 (14)	0.0800 (16)	0.0536 (12)	0.0098 (12)	0.0121 (11)	−0.0115 (11)
C3	0.0989 (17)	0.0794 (16)	0.0556 (12)	0.0180 (13)	0.0296 (12)	0.0126 (12)
C4	0.0986 (16)	0.0607 (13)	0.0737 (14)	−0.0022 (12)	0.0307 (12)	0.0121 (12)
C5	0.0756 (13)	0.0500 (11)	0.0558 (11)	−0.0020 (10)	0.0165 (10)	0.0012 (9)
C6	0.0404 (9)	0.0472 (10)	0.0460 (9)	0.0028 (8)	0.0029 (7)	0.0011 (8)
C7	0.0419 (9)	0.0482 (10)	0.0551 (11)	−0.0026 (9)	0.0047 (8)	−0.0004 (9)
C8	0.0428 (10)	0.0525 (11)	0.0535 (10)	−0.0009 (8)	0.0123 (8)	−0.0020 (9)
C9	0.0647 (14)	0.0757 (15)	0.0978 (17)	0.0049 (11)	−0.0104 (12)	−0.0315 (13)
C10	0.0520 (11)	0.0610 (12)	0.0506 (10)	−0.0034 (9)	0.0080 (8)	−0.0118 (10)
C11	0.0696 (14)	0.0793 (16)	0.0770 (15)	−0.0203 (12)	0.0163 (12)	0.0001 (13)
C12	0.111 (2)	0.0912 (19)	0.0740 (16)	0.0015 (16)	−0.0066 (14)	0.0191 (14)
C13	0.0762 (17)	0.112 (2)	0.0938 (18)	−0.0056 (17)	−0.0232 (14)	−0.0078 (18)
C14	0.0616 (15)	0.1010 (19)	0.1084 (19)	−0.0252 (14)	−0.0010 (14)	−0.0004 (17)
C15	0.0727 (15)	0.0719 (14)	0.0700 (13)	−0.0121 (12)	0.0078 (11)	0.0034 (11)

Geometric parameters (Å, º)

O1—C7	1.215 (2)	C7—C8	1.520 (2)
O2—C8	1.391 (2)	C8—H8	0.980
O2—H2	0.8200	C9—C10	1.499 (3)
O3—C8	1.401 (2)	C9—H9A	0.9700
O3—C9	1.422 (2)	C9—H9B	0.9700
C1—C2	1.378 (3)	C10—C11	1.361 (3)
C1—C6	1.385 (2)	C10—C15	1.366 (3)
C1—H1	0.9300	C11—C12	1.383 (3)
C2—C3	1.368 (3)	C11—H11	0.9300
C2—H2A	0.9300	C12—C13	1.363 (3)
C3—C4	1.368 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.346 (3)
C4—C5	1.383 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.375 (3)
C5—C6	1.386 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.485 (2)
C8—O2—H2	109.5	O3—C8—H8	110.7
C8—O3—C9	113.9 (1)	C7—C8—H8	110.7
C2—C1—C6	121.06 (19)	O3—C9—C10	110.12 (16)
C2—C1—H1	119.5	O3—C9—H9A	109.6
C6—C1—H1	119.5	C10—C9—H9A	109.6
C3—C2—C1	119.6 (2)	O3—C9—H9B	109.6
C3—C2—H2A	120.2	C10—C9—H9B	109.6
C1—C2—H2A	120.2	H9A—C9—H9B	108.2
C4—C3—C2	120.42 (19)	C11—C10—C15	118.26 (19)
C4—C3—H3	119.8	C11—C10—C9	121.16 (18)
C2—C3—H3	119.8	C15—C10—C9	120.5 (2)
C3—C4—C5	120.2 (2)	C10—C11—C12	120.9 (2)
C3—C4—H4	119.9	C10—C11—H11	119.6
C5—C4—H4	119.9	C12—C11—H11	119.6
C4—C5—C6	120.19 (19)	C13—C12—C11	119.5 (2)
C4—C5—H5	119.9	C13—C12—H12	120.3
C6—C5—H5	119.9	C11—C12—H12	120.3
C1—C6—C5	118.46 (16)	C14—C13—C12	120.3 (2)
C1—C6—C7	118.29 (16)	C14—C13—H13	119.8
C5—C6—C7	123.24 (16)	C12—C13—H13	119.8
O1—C7—C6	120.90 (16)	C13—C14—C15	119.8 (2)
O1—C7—C8	119.74 (16)	C13—C14—H14	120.1
C6—C7—C8	119.36 (15)	C15—C14—H14	120.1
O2—C8—O3	112.1 (2)	C10—C15—C14	121.2 (2)
O2—C8—C7	108.5 (1)	C10—C15—H15	119.4
O3—C8—C7	104.04 (13)	C14—C15—H15	119.4
O2—C8—H8	110.7
C6—C1—C2—C3	1.6 (3)	C6—C7—C8—O2	169.5 (1)
C1—C2—C3—C4	−1.5 (3)	O3—C8—O2—H2	90.0
C2—C3—C4—C5	0.2 (3)	O1—C7—C8—O3	108.37 (17)
C3—C4—C5—C6	1.0 (3)	C6—C7—C8—O3	−71.06 (18)
C2—C1—C6—C5	−0.3 (3)	C8—O3—C9—C10	162.35 (16)
C2—C1—C6—C7	−179.94 (16)	O3—C9—C10—C11	−52.3 (3)
C4—C5—C6—C1	−1.0 (3)	O3—C9—C10—C15	129.7 (2)
C4—C5—C6—C7	178.62 (17)	C15—C10—C11—C12	1.4 (3)
C1—C6—C7—O1	5.2 (2)	C9—C10—C11—C12	−176.7 (2)
C5—C6—C7—O1	−174.42 (17)	C10—C11—C12—C13	−0.3 (4)
C1—C6—C7—C8	−175.40 (15)	C11—C12—C13—C14	−1.2 (4)
C5—C6—C7—C8	5.0 (2)	C12—C13—C14—C15	1.7 (4)
C9—O3—C8—O2	−80.2 (2)	C11—C10—C15—C14	−0.9 (3)
C9—O3—C8—C7	162.80 (16)	C9—C10—C15—C14	177.2 (2)
O1—C7—C8—O2	−11.1 (2)	C13—C14—C15—C10	−0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	2.19	2.864 (2)	140 (1)
O2—H2···O2^i	0.82	2.25	2.986 (2)	149 (1)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.