Methyl 2-benz­yloxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate monohydrate

The crystal structure of the title compound, C₁₂H₁₄O₅·H₂O, displays a supramolecular structure via O—H...O hydrogen bonds. No π–π stacking is observed.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.045
• wR factor = 0.155
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); 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, 2001); software used to prepare material for publication: SHELXTL.

Methyl 2-benzyloxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate monohydrate

Crystal data

C12H14O5·H2O	F(000) = 544
Mr = 256.25	Dx = 1.361 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2626 reflections
a = 8.3939 (10) Å	θ = 2.5–26.9°
b = 15.8376 (19) Å	µ = 0.11 mm^−1
c = 9.9983 (12) Å	T = 292 K
β = 109.821 (2)°	Block, colorless
V = 1250.4 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2197 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 27.0°, θmin = 2.5°
φ and ω scans	h = −10→10
7256 measured reflections	k = −17→20
2718 independent reflections	l = −9→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0916P)^2 + 0.0507P] where P = (Fo^2 + 2Fc^2)/3
2718 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.35 e Å^−3
3 restraints	Δρmin = −0.27 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 > 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
C1	0.4520 (2)	0.13135 (10)	0.74434 (16)	0.0367 (4)
C2	0.5828 (2)	0.18882 (11)	0.79866 (18)	0.0425 (4)
H2	0.6634	0.1964	0.7548	0.051*
C3	0.5920 (2)	0.23434 (10)	0.9177 (2)	0.0447 (4)
H3	0.6799	0.2726	0.9547	0.054*
C4	0.4723 (2)	0.22425 (10)	0.98383 (18)	0.0408 (4)
H4	0.4804	0.2557	1.0644	0.049*
C5	0.34069 (19)	0.16728 (9)	0.93007 (15)	0.0325 (3)
C6	0.33103 (18)	0.12021 (9)	0.80984 (16)	0.0318 (3)
C7	0.1924 (2)	0.05724 (10)	0.74670 (16)	0.0364 (4)
C8	0.1237 (3)	−0.08791 (13)	0.7363 (3)	0.0695 (6)
H8A	0.0410	−0.0817	0.7824	0.104*
H8B	0.1792	−0.1415	0.7611	0.104*
H8C	0.0687	−0.0850	0.6351	0.104*
C9	0.0603 (2)	0.22007 (12)	0.9366 (2)	0.0512 (5)
H9A	0.0087	0.2086	0.8369	0.077*
H9B	0.1023	0.2769	0.9496	0.077*
H9C	−0.0222	0.2132	0.9828	0.077*
C10	0.20513 (19)	0.15945 (10)	1.00040 (16)	0.0359 (4)
C11	0.3438 (3)	0.09715 (13)	1.2127 (2)	0.0573 (5)
H11A	0.3192	0.0886	1.2997	0.069*
H11B	0.4656	0.0958	1.2347	0.069*
C12	0.2590 (3)	0.03046 (12)	1.10458 (19)	0.0551 (5)
H12A	0.3412	0.0009	1.0731	0.066*
H12B	0.2006	−0.0102	1.1439	0.066*
O1	0.43534 (17)	0.08397 (9)	0.62630 (14)	0.0517 (4)
H1	0.521 (2)	0.0829 (16)	0.604 (3)	0.078*
O2	0.24740 (15)	−0.02094 (7)	0.78169 (13)	0.0481 (3)
O3	0.05202 (16)	0.07534 (9)	0.66989 (14)	0.0560 (4)
O4	0.27572 (15)	0.17512 (8)	1.14829 (12)	0.0458 (3)
O5	0.14156 (14)	0.07610 (7)	0.98974 (12)	0.0406 (3)
O6	0.70036 (17)	0.06429 (10)	0.53946 (15)	0.0568 (4)
H6A	0.8034 (15)	0.0683 (17)	0.588 (3)	0.085*
H6B	0.679 (3)	0.0238 (12)	0.485 (2)	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0373 (8)	0.0380 (8)	0.0354 (8)	0.0003 (6)	0.0132 (6)	0.0008 (6)
C2	0.0371 (9)	0.0434 (9)	0.0500 (10)	−0.0043 (7)	0.0185 (7)	0.0048 (7)
C3	0.0379 (9)	0.0354 (8)	0.0582 (10)	−0.0099 (7)	0.0129 (8)	−0.0018 (7)
C4	0.0409 (9)	0.0350 (8)	0.0440 (9)	−0.0027 (6)	0.0109 (7)	−0.0063 (7)
C5	0.0309 (8)	0.0301 (7)	0.0343 (7)	0.0035 (5)	0.0082 (6)	0.0018 (6)
C6	0.0271 (7)	0.0322 (7)	0.0352 (8)	0.0007 (6)	0.0092 (6)	0.0017 (6)
C7	0.0347 (8)	0.0429 (9)	0.0339 (8)	−0.0052 (6)	0.0147 (7)	−0.0065 (6)
C8	0.0756 (15)	0.0493 (11)	0.0910 (16)	−0.0287 (10)	0.0380 (13)	−0.0198 (11)
C9	0.0415 (10)	0.0569 (11)	0.0545 (11)	0.0148 (8)	0.0152 (8)	0.0026 (8)
C10	0.0346 (8)	0.0380 (8)	0.0342 (8)	0.0028 (6)	0.0106 (6)	−0.0025 (6)
C11	0.0564 (12)	0.0647 (12)	0.0448 (10)	0.0064 (9)	0.0091 (9)	0.0130 (9)
C12	0.0652 (12)	0.0488 (10)	0.0517 (11)	0.0089 (9)	0.0203 (9)	0.0131 (9)
O1	0.0462 (8)	0.0682 (8)	0.0489 (7)	−0.0131 (6)	0.0270 (6)	−0.0178 (6)
O2	0.0462 (7)	0.0358 (6)	0.0663 (8)	−0.0076 (5)	0.0242 (6)	−0.0110 (5)
O3	0.0388 (7)	0.0683 (9)	0.0498 (7)	−0.0085 (6)	0.0004 (6)	−0.0020 (6)
O4	0.0492 (7)	0.0523 (7)	0.0349 (6)	0.0065 (5)	0.0131 (5)	−0.0050 (5)
O5	0.0379 (6)	0.0414 (6)	0.0441 (6)	−0.0021 (5)	0.0159 (5)	0.0014 (5)
O6	0.0410 (7)	0.0730 (10)	0.0581 (8)	−0.0050 (7)	0.0192 (6)	−0.0187 (7)

Geometric parameters (Å, º)

C1—O1	1.365 (2)	C8—H8C	0.9600
C1—C2	1.387 (2)	C9—C10	1.510 (2)
C1—C6	1.393 (2)	C9—H9A	0.9600
C2—C3	1.371 (3)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
C3—C4	1.386 (3)	C10—O5	1.4142 (19)
C3—H3	0.9300	O4—C10	1.4158 (19)
C4—C5	1.386 (2)	C11—O4	1.420 (2)
C4—H4	0.9300	C11—C12	1.506 (3)
C5—C6	1.393 (2)	C11—H11A	0.9700
C5—C10	1.532 (2)	C11—H11B	0.9700
C6—C7	1.500 (2)	C12—O5	1.430 (2)
C7—O3	1.203 (2)	C12—H12A	0.9700
C7—O2	1.326 (2)	C12—H12B	0.9700
C8—O2	1.446 (2)	O1—H1	0.821 (10)
C8—H8A	0.9600	O6—H6A	0.839 (10)
C8—H8B	0.9600	O6—H6B	0.823 (10)
O1—C1—C2	122.29 (15)	C10—C9—H9B	109.5
O1—C1—C6	117.36 (14)	H9A—C9—H9B	109.5
C2—C1—C6	120.34 (15)	C10—C9—H9C	109.5
C3—C2—C1	119.26 (16)	H9A—C9—H9C	109.5
C3—C2—H2	120.4	H9B—C9—H9C	109.5
C1—C2—H2	120.4	O5—C10—O4	104.83 (13)
C2—C3—C4	121.12 (15)	O5—C10—C9	109.42 (14)
C2—C3—H3	119.4	O4—C10—C9	108.75 (13)
C4—C3—H3	119.4	O5—C10—C5	111.16 (12)
C5—C4—C3	120.09 (15)	O4—C10—C5	110.62 (12)
C5—C4—H4	120.0	C9—C10—C5	111.80 (14)
C3—C4—H4	120.0	O4—C11—C12	105.35 (14)
C4—C5—C6	119.23 (15)	O4—C11—H11A	110.7
C4—C5—C10	119.56 (14)	C12—C11—H11A	110.7
C6—C5—C10	121.17 (13)	O4—C11—H11B	110.7
C1—C6—C5	119.95 (14)	C12—C11—H11B	110.7
C1—C6—C7	118.13 (13)	H11A—C11—H11B	108.8
C5—C6—C7	121.92 (13)	O5—C12—C11	104.55 (14)
O3—C7—O2	124.69 (15)	O5—C12—H12A	110.8
O3—C7—C6	124.24 (15)	C11—C12—H12A	110.8
O2—C7—C6	111.00 (13)	O5—C12—H12B	110.8
O2—C8—H8A	109.5	C11—C12—H12B	110.8
O2—C8—H8B	109.5	H12A—C12—H12B	108.9
H8A—C8—H8B	109.5	C1—O1—H1	113.9 (18)
O2—C8—H8C	109.5	C7—O2—C8	116.94 (15)
H8A—C8—H8C	109.5	C10—O4—C11	106.41 (13)
H8B—C8—H8C	109.5	C10—O5—C12	105.75 (13)
C10—C9—H9A	109.5	H6A—O6—H6B	113 (3)
O1—C1—C2—C3	−179.97 (15)	C4—C5—C10—O5	−148.21 (14)
C6—C1—C2—C3	0.2 (2)	C6—C5—C10—O5	34.01 (19)
C1—C2—C3—C4	−0.4 (3)	C4—C5—C10—O4	−32.18 (19)
C2—C3—C4—C5	0.1 (3)	C6—C5—C10—O4	150.04 (14)
C3—C4—C5—C6	0.4 (2)	C4—C5—C10—C9	89.18 (18)
C3—C4—C5—C10	−177.42 (14)	C6—C5—C10—C9	−88.60 (17)
O1—C1—C6—C5	−179.51 (14)	O4—C11—C12—O5	−3.2 (2)
C2—C1—C6—C5	0.4 (2)	O3—C7—O2—C8	−7.0 (2)
O1—C1—C6—C7	0.1 (2)	C6—C7—O2—C8	175.77 (15)
C2—C1—C6—C7	−179.98 (14)	O5—C10—O4—C11	34.29 (17)
C4—C5—C6—C1	−0.6 (2)	C9—C10—O4—C11	151.23 (15)
C10—C5—C6—C1	177.14 (13)	C5—C10—O4—C11	−85.62 (16)
C4—C5—C6—C7	179.71 (14)	C12—C11—O4—C10	−18.8 (2)
C10—C5—C6—C7	−2.5 (2)	O4—C10—O5—C12	−36.30 (16)
C1—C6—C7—O3	−99.19 (19)	C9—C10—O5—C12	−152.78 (14)
C5—C6—C7—O3	80.5 (2)	C5—C10—O5—C12	83.24 (15)
C1—C6—C7—O2	78.01 (17)	C11—C12—O5—C10	23.96 (19)
C5—C6—C7—O2	−102.33 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3^i	0.82 (2)	1.97 (1)	2.799 (2)	170 (3)
O6—H6B···O1^ii	0.82 (1)	2.08 (1)	2.877 (2)	162 (2)
O1—H1···O6	0.82 (1)	1.85 (1)	2.666 (2)	171 (3)

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